data_6a
_audit_creation_date               2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C23 H27 N3 O2'
_chemical_formula_sum              'C23 H27 N3 O2'
_chemical_formula_weight           377.47
_chemical_melting_point            ?
_chemical_oxdiff_formula           C20
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     13.5506(7)
_cell_length_b                     9.7144(3)
_cell_length_c                     15.9727(10)
_cell_angle_alpha                  90
_cell_angle_beta                   111.673(6)
_cell_angle_gamma                  90
_cell_volume                       1953.94(19)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      4040
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        31.1070
_cell_measurement_theta_min        3.2560
_shelx_estimated_absorpt_T_max     0.984
_shelx_estimated_absorpt_T_min     0.984
_exptl_absorpt_coefficient_mu      0.083
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.89534
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.283
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               808
_exptl_crystal_size_max            0.2
_exptl_crystal_size_mid            0.2
_exptl_crystal_size_min            0.2
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0250
_diffrn_reflns_av_unetI/netI       0.0306
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              11449
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.498
_diffrn_reflns_theta_min           2.648
_diffrn_ambient_temperature        100(2)
_diffrn_detector_area_resol_mean   8.1048
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -37.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  178.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00  -37.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   87.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   52.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -19.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00   97.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -       24.4558   19.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega  -60.00  -35.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -99.00  -74.00   1.0000   30.0100
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  178.0000 -120.0000 25
;
_diffrn_measurement_device_type    'Xcalibur, Eos'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        -0.0443293000
_diffrn_orient_matrix_UB_12        0.0355862000
_diffrn_orient_matrix_UB_13        -0.0307171000
_diffrn_orient_matrix_UB_21        0.0328261000
_diffrn_orient_matrix_UB_22        0.0283538000
_diffrn_orient_matrix_UB_23        -0.0214736000
_diffrn_orient_matrix_UB_31        -0.0114155000
_diffrn_orient_matrix_UB_32        -0.0569694000
_diffrn_orient_matrix_UB_33        -0.0297635000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3754
_reflns_number_total               4497
_reflns_odcompleteness_completeness  99.87
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       28.98
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max           1.848
_refine_diff_density_min           -0.226
_refine_diff_density_rms           0.058
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       262
_refine_ls_number_reflns           4497
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0681
_refine_ls_R_factor_gt             0.0562
_refine_ls_restrained_S_all        1.038
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0660P)²+1.9413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1418
_refine_ls_wR_factor_ref           0.1500
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C9(H9), C14(H14), C16(H16), C4(H4), C8(H8), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?

# start Validation Reply Form
_vrf_PLAT094_7680-9379_sp-8_recryst
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       8.18 Report
RESPONSE: The structure contains an artifact of 
electron density, apparently connected with packing defects. 
Unfortunately, with recrystallization this peak becomes smaller, 
but is systematically reproduced.
;
_vrf_PLAT097_7680-9379_sp-8_recryst
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.85 eA-3  
RESPONSE: The structure contains an artifact of 
electron density, apparently connected with packing defects. 
Unfortunately, with recrystallization this peak becomes smaller, 
but is systematically reproduced.
;
# end Validation Reply Form

loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.67053(10) 0.67696(13) 0.13135(9) 0.0201(3) Uani 1 1 d . . . . .
 O2 O 0.69445(10) 0.18989(13) 0.13869(9) 0.0217(3) Uani 1 1 d . . . . .
 N1 N 0.42980(12) 0.56429(15) 0.28016(10) 0.0176(3) Uani 1 1 d . . . . .
 N3 N 0.47149(13) 0.79540(16) 0.09010(11) 0.0202(3) Uani 1 1 d . . . . .
 H3 H 0.5336(19) 0.794(2) 0.0809(15) 0.024 Uiso 1 1 d R . . . .
 N2 N 0.29464(13) 0.60164(16) 0.37818(11) 0.0200(3) Uani 1 1 d . . . . .
 C10 C 0.34891(13) 0.65912(17) 0.12818(12) 0.0155(3) Uani 1 1 d . . . . .
 C15 C 0.63060(14) 0.30197(18) 0.13086(12) 0.0174(4) Uani 1 1 d . . . . .
 C13 C 0.62506(14) 0.55044(18) 0.12902(11) 0.0155(3) Uani 1 1 d . . . . .
 C12 C 0.51644(13) 0.54855(18) 0.11916(12) 0.0153(3) Uani 1 1 d . . . . .
 C1 C 0.34078(13) 0.60814(17) 0.20729(12) 0.0151(3) Uani 1 1 d . . . . .
 C17 C 0.46956(14) 0.41932(19) 0.11428(12) 0.0180(4) Uani 1 1 d . . . . .
 H17 H 0.3969 0.4153 0.1074 0.022 Uiso 1 1 calc R . . . .
 C2 C 0.23584(13) 0.59538(17) 0.21167(12) 0.0156(3) Uani 1 1 d . . . . .
 C11 C 0.45211(14) 0.67514(18) 0.11347(12) 0.0157(3) Uani 1 1 d . . . . .
 C9 C 0.25641(14) 0.68891(18) 0.05197(12) 0.0180(4) Uani 1 1 d . . . . .
 H9 H 0.2631 0.7326 0.0011 0.022 Uiso 1 1 calc R . . . .
 C14 C 0.68091(14) 0.42890(18) 0.13614(12) 0.0171(4) Uani 1 1 d . . . . .
 H14 H 0.7541 0.4319 0.1447 0.021 Uiso 1 1 calc R . . . .
 C16 C 0.52362(14) 0.29629(18) 0.11897(12) 0.0186(4) Uani 1 1 d . . . . .
 H16 H 0.4884 0.2104 0.1142 0.022 Uiso 1 1 calc R . . . .
 C7 C 0.14534(14) 0.60491(18) 0.12934(12) 0.0170(4) Uani 1 1 d . . . . .
 C3 C 0.21565(14) 0.57185(17) 0.29370(12) 0.0171(4) Uani 1 1 d . . . . .
 C4 C 0.11643(15) 0.52181(18) 0.28637(13) 0.0204(4) Uani 1 1 d . . . . .
 H4 H 0.1055 0.4922 0.3390 0.025 Uiso 1 1 calc R . . . .
 C8 C 0.15789(14) 0.65569(19) 0.05057(12) 0.0187(4) Uani 1 1 d . . . . .
 H8 H 0.0975 0.6666 -0.0034 0.022 Uiso 1 1 calc R . . . .
 C6 C 0.04290(14) 0.56293(19) 0.12597(13) 0.0208(4) Uani 1 1 d . . . . .
 H6 H -0.0171 0.5687 0.0713 0.025 Uiso 1 1 calc R . . . .
 C23 C 0.64395(16) 0.05771(19) 0.11955(14) 0.0237(4) Uani 1 1 d . . . . .
 H23A H 0.5934 0.0558 0.0571 0.036 Uiso 1 1 calc GR . . . .
 H23B H 0.6062 0.0409 0.1604 0.036 Uiso 1 1 calc GR . . . .
 H23C H 0.6978 -0.0138 0.1281 0.036 Uiso 1 1 calc GR . . . .
 C20 C 0.53064(14) 0.6361(2) 0.31190(13) 0.0212(4) Uani 1 1 d . . . . .
 H20A H 0.5826 0.5835 0.2956 0.032 Uiso 1 1 calc GR . . . .
 H20B H 0.5559 0.6460 0.3775 0.032 Uiso 1 1 calc GR . . . .
 H20C H 0.5216 0.7274 0.2840 0.032 Uiso 1 1 calc GR . . . .
 C5 C 0.03241(14) 0.51440(19) 0.20257(14) 0.0216(4) Uani 1 1 d . . . . .
 H5 H -0.0331 0.4748 0.1990 0.026 Uiso 1 1 calc R . . . .
 C22 C 0.77897(14) 0.6813(2) 0.13903(14) 0.0229(4) Uani 1 1 d . . . . .
 H22A H 0.7865 0.6322 0.0881 0.034 Uiso 1 1 calc GR . . . .
 H22B H 0.8237 0.6373 0.1955 0.034 Uiso 1 1 calc GR . . . .
 H22C H 0.8010 0.7773 0.1387 0.034 Uiso 1 1 calc GR . . . .
 C21 C 0.43258(15) 0.42874(19) 0.31906(13) 0.0220(4) Uani 1 1 d . . . . .
 H21A H 0.3621 0.3865 0.2933 0.033 Uiso 1 1 calc GR . . . .
 H21B H 0.4534 0.4371 0.3845 0.033 Uiso 1 1 calc GR . . . .
 H21C H 0.4842 0.3710 0.3056 0.033 Uiso 1 1 calc GR . . . .
 C18 C 0.33685(15) 0.7420(2) 0.38877(13) 0.0226(4) Uani 1 1 d . . . . .
 H18A H 0.3450 0.7710 0.3329 0.034 Uiso 1 1 calc GR . . . .
 H18B H 0.4061 0.7446 0.4384 0.034 Uiso 1 1 calc GR . . . .
 H18C H 0.2877 0.8044 0.4020 0.034 Uiso 1 1 calc GR . . . .
 C19 C 0.27274(17) 0.5604(2) 0.45750(13) 0.0257(4) Uani 1 1 d . . . . .
 H19A H 0.2145 0.6163 0.4616 0.039 Uiso 1 1 calc GR . . . .
 H19B H 0.3365 0.5743 0.5117 0.039 Uiso 1 1 calc GR . . . .
 H19C H 0.2525 0.4630 0.4524 0.039 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C13 1.369(2) . ?
 O1 C22 1.429(2) . ?
 O2 C15 1.367(2) . ?
 O2 C23 1.434(2) . ?
 N1 C1 1.398(2) . ?
 N1 C20 1.449(2) . ?
 N1 C21 1.451(2) . ?
 N3 H3 0.91(2) . ?
 N3 C11 1.283(2) . ?
 N2 C3 1.408(2) . ?
 N2 C18 1.464(2) . ?
 N2 C19 1.460(2) . ?
 C10 C1 1.399(2) . ?
 C10 C11 1.509(2) . ?
 C10 C9 1.418(2) . ?
 C15 C14 1.396(2) . ?
 C15 C16 1.392(2) . ?
 C13 C12 1.422(2) . ?
 C13 C14 1.384(2) . ?
 C12 C17 1.396(2) . ?
 C12 C11 1.491(2) . ?
 C1 C2 1.455(2) . ?
 C17 H17 0.9500 . ?
 C17 C16 1.389(2) . ?
 C2 C7 1.432(2) . ?
 C2 C3 1.452(2) . ?
 C9 H9 0.9500 . ?
 C9 C8 1.366(2) . ?
 C14 H14 0.9500 . ?
 C16 H16 0.9500 . ?
 C7 C8 1.419(3) . ?
 C7 C6 1.429(2) . ?
 C3 C4 1.393(2) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.403(3) . ?
 C8 H8 0.9500 . ?
 C6 H6 0.9500 . ?
 C6 C5 1.367(3) . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 0.9800 . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C5 H5 0.9500 . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C13 O1 C22 117.82(13) . . ?
 C15 O2 C23 117.22(14) . . ?
 C1 N1 C20 123.85(15) . . ?
 C1 N1 C21 120.74(15) . . ?
 C20 N1 C21 114.54(15) . . ?
 C11 N3 H3 109.5(15) . . ?
 C3 N2 C18 115.36(15) . . ?
 C3 N2 C19 116.68(15) . . ?
 C19 N2 C18 110.55(15) . . ?
 C1 C10 C11 124.32(16) . . ?
 C1 C10 C9 120.55(15) . . ?
 C9 C10 C11 114.93(15) . . ?
 O2 C15 C14 114.78(15) . . ?
 O2 C15 C16 124.95(16) . . ?
 C16 C15 C14 120.26(16) . . ?
 O1 C13 C12 116.85(15) . . ?
 O1 C13 C14 122.45(15) . . ?
 C14 C13 C12 120.70(16) . . ?
 C13 C12 C11 123.67(15) . . ?
 C17 C12 C13 116.68(15) . . ?
 C17 C12 C11 119.65(15) . . ?
 N1 C1 C10 121.89(15) . . ?
 N1 C1 C2 119.49(15) . . ?
 C10 C1 C2 118.57(16) . . ?
 C12 C17 H17 118.3 . . ?
 C16 C17 C12 123.41(16) . . ?
 C16 C17 H17 118.3 . . ?
 C7 C2 C1 118.10(15) . . ?
 C7 C2 C3 117.13(15) . . ?
 C3 C2 C1 124.76(16) . . ?
 N3 C11 C10 116.12(15) . . ?
 N3 C11 C12 126.24(16) . . ?
 C12 C11 C10 117.39(14) . . ?
 C10 C9 H9 119.5 . . ?
 C8 C9 C10 120.99(17) . . ?
 C8 C9 H9 119.5 . . ?
 C15 C14 H14 119.7 . . ?
 C13 C14 C15 120.55(16) . . ?
 C13 C14 H14 119.7 . . ?
 C15 C16 H16 120.8 . . ?
 C17 C16 C15 118.37(16) . . ?
 C17 C16 H16 120.8 . . ?
 C8 C7 C2 119.63(16) . . ?
 C8 C7 C6 119.92(17) . . ?
 C6 C7 C2 120.45(16) . . ?
 N2 C3 C2 120.16(15) . . ?
 C4 C3 N2 121.37(16) . . ?
 C4 C3 C2 118.46(17) . . ?
 C3 C4 H4 119.5 . . ?
 C3 C4 C5 121.07(17) . . ?
 C5 C4 H4 119.5 . . ?
 C9 C8 C7 120.28(17) . . ?
 C9 C8 H8 119.9 . . ?
 C7 C8 H8 119.9 . . ?
 C7 C6 H6 120.5 . . ?
 C5 C6 C7 119.05(18) . . ?
 C5 C6 H6 120.5 . . ?
 O2 C23 H23A 109.5 . . ?
 O2 C23 H23B 109.5 . . ?
 O2 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?
 N1 C20 H20A 109.5 . . ?
 N1 C20 H20B 109.5 . . ?
 N1 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C4 C5 H5 119.3 . . ?
 C6 C5 C4 121.36(17) . . ?
 C6 C5 H5 119.3 . . ?
 O1 C22 H22A 109.5 . . ?
 O1 C22 H22B 109.5 . . ?
 O1 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 N1 C21 H21A 109.5 . . ?
 N1 C21 H21B 109.5 . . ?
 N1 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 N2 C18 H18A 109.5 . . ?
 N2 C18 H18B 109.5 . . ?
 N2 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 N2 C19 H19A 109.5 . . ?
 N2 C19 H19B 109.5 . . ?
 N2 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_6b
_audit_creation_date               2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'B F4, C23 H28 N3 O2, C2 H6 O'
_chemical_formula_sum              'C25 H34 B F4 N3 O3'
_chemical_formula_weight           511.36
_chemical_melting_point            ?
_chemical_oxdiff_formula           'N3 C18 F4 B O2'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     7.61226(12)
_cell_length_b                     21.1202(4)
_cell_length_c                     15.7463(2)
_cell_angle_alpha                  90
_cell_angle_beta                   91.5601(14)
_cell_angle_gamma                  90
_cell_volume                       2530.63(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      20545
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        71.9450
_cell_measurement_theta_min        2.1540
_shelx_estimated_absorpt_T_max     0.876
_shelx_estimated_absorpt_T_min     0.826
_exptl_absorpt_coefficient_mu      0.906
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.55118
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.342
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               1080
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.22
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.15
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0343
_diffrn_reflns_av_unetI/netI       0.0188
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         25
_diffrn_reflns_limit_k_min         -25
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              28374
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           71.863
_diffrn_reflns_theta_min           3.502
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              HyPix3000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -104.00 -56.00   0.50    0.20    --  -41.22 -47.00 -21.00   96
  2  ω    -55.00 -23.00   0.50    0.20    --  -41.22  47.00 127.00   64
  3  ω     42.00  70.00   0.50    0.20    --   41.22  47.00 127.00   56
  4  ω    132.00 157.00   0.50    0.20    --  101.00  47.00 127.00   50
  5  ω     88.00 114.00   0.50    0.20    --  101.00  47.00 127.00   52
  6  ω     68.00 116.00   0.50    0.20    --  101.00 -47.00 -21.00   96
  7  ω    -55.00  16.00   0.50    0.20    --  -41.22  54.00 -90.00  142
  8  ω    -57.00  18.00   0.50    0.20    --  -41.22  54.00-150.00  150
  9  ω     16.00  53.00   0.50    0.20    --   41.22 -65.00 -30.00   74
 10  ω     26.00  86.00   0.50    0.20    --   41.22  54.00 -90.00  120
 11  ω     33.00 102.00   0.50    0.20    --   41.22  43.00-150.00  138
 12  ω    -17.00   9.00   0.50    0.20    --   41.22 -65.00 -30.00   52
 13  ω    -18.00  55.00   0.50    0.20    --   41.22 -43.00  60.00  146
 14  ω    -10.00  36.00   0.50    0.20    --   41.22 -47.00 -21.00   92
 15  ω    -31.00   4.00   0.50    0.20    --   41.22 -11.00-150.00   70
 16  ω     14.00  52.00   0.50    0.20    --   41.22 -11.00-150.00   76
 17  ω     32.00  57.00   0.50    0.20    --   41.22  21.00 120.00   50
 18  ω    125.00 155.00   0.50    0.20    --  101.00  93.00-150.00   60
 19  ω     98.00 157.00   0.50    0.20    --  101.00  33.00 120.00  118
 20  ω     52.00 119.00   0.50    0.20    --  101.00 -59.00 -90.00  134
 21  ω     93.00 119.00   0.50    0.20    --  101.00  93.00-150.00   52
 22  ω     66.00  92.00   0.50    0.20    --  101.00 -68.00-150.00   52
 23  ω    109.00 157.00   0.50    0.20    --  101.00   8.00  60.00   96
 24  ω    102.00 150.00   0.50    0.20    --  101.00  33.00 -90.00   96
 25  ω     48.00 119.00   0.50    0.20    --  101.00 -59.00-180.00  142
 26  ω     92.00 130.00   0.50    0.20    --  101.00  33.00  90.00   76
 27  ω    102.00 127.00   0.50    0.20    --  101.00  33.00   0.00   50
 28  ω     99.00 130.00   0.50    0.20    --  101.00  25.00-120.00   62
 29  ω     79.00 108.00   0.50    0.20    --  101.00 -33.00 -60.00   58
 30  ω     43.00  69.00   0.50    0.20    --  101.00 -33.00 -60.00   52
 31  ω     82.00 110.00   0.50    0.20    --  101.00  93.00-180.00   56
 32  ω     80.00 150.00   0.50    0.20    --  101.00  68.00 150.00  140
 33  ω     43.00 110.00   0.50    0.20    --  101.00 -33.00-180.00  134
 34  ω     48.00 106.00   0.50    0.20    --  101.00 -42.00 120.00  116
 35  ω    -19.00  19.00   0.50    0.20    --  -41.22  47.00 127.00   76
 36  ω    -43.00 -16.00   0.50    0.20    --  -41.22 -77.00 -90.00   54
 37  ω   -105.00 -80.00   0.50    0.20    --  -41.22 -77.00 -90.00   50
 38  ω     33.00  73.00   0.50    0.20    --   41.22  32.00 -90.00   80
 39  ω     59.00  85.00   0.50    0.20    --   41.22  77.00 -90.00   52
 40  ω     22.00  55.00   0.50    0.20    --   41.22  77.00 -60.00   66
 41  ω      7.00  33.00   0.50    0.20    --   41.22 -43.00 150.00   52
 42  ω     35.00  62.00   0.50    0.20    --   41.22  43.00-180.00   54
 43  ω     22.00  47.00   0.50    0.20    --   41.22  77.00 -90.00   50
 44  ω     87.00 113.00   0.50    0.20    --  101.00  50.00  60.00   52
 45  ω     91.00 144.00   0.50    0.20    --  101.00  50.00 -60.00  106
 46  ω     83.00 109.00   0.50    0.20    --  101.00 -17.00  90.00   52
 47  ω     30.00  72.00   0.50    0.20    --  101.00 -17.00-180.00   84
 48  ω     89.00 114.00   0.50    0.20    --  101.00 -17.00-180.00   50
 49  ω     82.00 108.00   0.50    0.20    --  101.00  77.00 150.00   52
 50  ω    132.00 157.00   0.50    0.20    --  101.00  68.00 -90.00   50
 51  ω    109.00 154.00   0.50    0.20    --  101.00  17.00   0.00   90
 52  ω    116.00 151.00   0.50    0.20    --  101.00  77.00-120.00   70
 53  ω    120.00 146.00   0.50    0.20    --  101.00  77.00-150.00   52
 54  ω     49.00  75.00   0.50    0.20    --  101.00 -17.00  90.00   52
 55  ω     76.00 102.00   0.50    0.20    --  101.00  77.00 -90.00   52
 56  ω     83.00 109.00   0.50    0.20    --  101.00  59.00-120.00   52
 57  ω     85.00 111.00   0.50    0.20    --  101.00  59.00-150.00   52
 58  ω     76.00 102.00   0.50    0.20    --  101.00  77.00-120.00   52
 59  ω    131.00 157.00   0.50    0.20    --  101.00  77.00-180.00   52
 60  ω     76.00 102.00   0.50    0.20    --  101.00  76.00-140.80   52
 61  ω     38.00  64.00   0.50    0.20    --  101.00 -68.00  30.00   52
 62  ω     84.00 120.00   0.50    0.20    --  101.00 -68.00  30.00   72
 63  ω     83.00 109.00   0.50    0.20    --  101.00  59.00-180.00   52
 64  ω     83.00 109.00   0.50    0.20    --  101.00  59.00 -90.00   52
 65  ω     85.00 111.00   0.50    0.20    --  101.00-111.00 -60.00   52
 66  ω     76.00 102.00   0.50    0.20    --  101.00  77.00-150.00   52
 67  ω    132.00 157.00   0.50    0.20    --  101.00  50.00-150.00   50
 68  ω     87.00 113.00   0.50    0.20    --  101.00  50.00-150.00   52
 69  ω     76.00 102.00   0.50    0.20    --  101.00  77.00-180.00   52
 70  ω     46.00  93.00   0.50    0.20    --  101.00 -42.00 -30.00   94
 71  ω     88.00 153.00   0.50    0.20    --  101.00  50.00-180.00  130
 72  ω     86.00 112.00   0.50    0.20    --  101.00  50.00 -90.00   52
 73  ω    131.00 156.00   0.50    0.20    --  101.00  50.00 -90.00   50
 74  ω     54.00  90.00   0.50    0.20    --  101.00 -33.00-120.00   72
 75  ω    130.00 156.00   0.50    0.20    --  101.00  77.00 150.00   52
 76  ω     80.00 106.00   0.50    0.20    --  101.00  68.00-150.00   52
 77  ω    129.00 157.00   0.50    0.20    --  101.00  50.00  60.00   56
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type   
 'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.1288116000
_diffrn_orient_matrix_UB_12        0.0252821000
_diffrn_orient_matrix_UB_13        0.0657299000
_diffrn_orient_matrix_UB_21        -0.1058218000
_diffrn_orient_matrix_UB_22        0.0338762000
_diffrn_orient_matrix_UB_23        -0.0713861000
_diffrn_orient_matrix_UB_31        -0.1148469000
_diffrn_orient_matrix_UB_32        -0.0594668000
_diffrn_orient_matrix_UB_33        -0.0126479000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4755
_reflns_number_total               4958
_reflns_odcompleteness_completeness  99.98
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       70.93
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection         'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction          'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.875
_refine_diff_density_min           -0.379
_refine_diff_density_rms           0.080
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       336
_refine_ls_number_reflns           4958
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0435
_refine_ls_R_factor_gt             0.0424
_refine_ls_restrained_S_all        1.027
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0615P)²+1.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1107
_refine_ls_wR_factor_ref           0.1117
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C6(H6), C14(H14), C8(H8), C7(H7), C16(H16), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C2S(H2SA,H2SB,H2SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F3 F 0.87462(12) 0.53298(4) 0.66254(6) 0.0276(2) Uani 1 1 d . . . . .
 F4 F 0.89657(12) 0.63814(4) 0.63483(7) 0.0349(2) Uani 1 1 d . . . . .
 F2 F 0.69771(13) 0.60337(5) 0.72926(6) 0.0356(2) Uani 1 1 d . . . . .
 F1 F 0.65423(14) 0.58350(5) 0.58906(7) 0.0413(3) Uani 1 1 d . . . . .
 O1 O 0.61692(12) 0.92820(5) 0.62689(6) 0.0204(2) Uani 1 1 d . . . . .
 O2 O 0.82384(13) 0.98536(5) 0.35666(6) 0.0233(2) Uani 1 1 d . . . . .
 O1S O 0.01886(13) 0.83581(5) 0.73756(6) 0.0246(2) Uani 1 1 d . . . . .
 H1S H 0.1037 0.8428 0.7058 0.037 Uiso 1 1 calc GR . . . .
 N3 N 0.28291(13) 0.60748(5) 0.48547(6) 0.0134(2) Uani 1 1 d . . . . .
 H3 H 0.3469 0.6395 0.5214 0.016 Uiso 1 1 calc R . . . .
 N2 N 0.37075(13) 0.71275(5) 0.55716(7) 0.0140(2) Uani 1 1 d . . . . .
 N1 N 0.30634(16) 0.86359(6) 0.63636(8) 0.0250(3) Uani 1 1 d . . . . .
 H1 H 0.386(3) 0.8912(9) 0.6616(12) 0.030 Uiso 1 1 d R . . . .
 C5 C 0.12506(16) 0.63936(6) 0.44994(8) 0.0137(2) Uani 1 1 d . . . . .
 C4 C 0.10693(15) 0.70611(6) 0.46298(8) 0.0131(2) Uani 1 1 d . . . . .
 C15 C 0.70196(17) 0.95212(6) 0.40041(9) 0.0175(3) Uani 1 1 d . . . . .
 C3 C 0.22868(16) 0.74540(6) 0.51068(8) 0.0134(2) Uani 1 1 d . . . . .
 C9 C -0.04180(16) 0.73555(6) 0.42147(8) 0.0149(3) Uani 1 1 d . . . . .
 C17 C 0.45280(17) 0.88464(6) 0.41589(9) 0.0175(3) Uani 1 1 d . . . . .
 H17 H 0.3621 0.8595 0.3906 0.021 Uiso 1 1 calc R . . . .
 C6 C 0.00594(17) 0.60487(6) 0.40218(8) 0.0170(3) Uani 1 1 d . . . . .
 H6 H 0.0226 0.5606 0.3950 0.020 Uiso 1 1 calc R . . . .
 C14 C 0.72021(17) 0.95669(6) 0.48882(9) 0.0171(3) Uani 1 1 d . . . . .
 H14 H 0.8129 0.9812 0.5135 0.020 Uiso 1 1 calc R . . . .
 C2 C 0.20830(16) 0.81044(6) 0.51126(8) 0.0160(3) Uani 1 1 d . . . . .
 C13 C 0.60376(17) 0.92561(6) 0.54050(8) 0.0158(3) Uani 1 1 d . . . . .
 C12 C 0.46374(16) 0.88857(6) 0.50469(8) 0.0158(3) Uani 1 1 d . . . . .
 C8 C -0.16358(16) 0.69874(7) 0.37282(8) 0.0170(3) Uani 1 1 d . . . . .
 H8 H -0.2623 0.7188 0.3462 0.020 Uiso 1 1 calc R . . . .
 C7 C -0.14111(17) 0.63490(7) 0.36367(8) 0.0182(3) Uani 1 1 d . . . . .
 H7 H -0.2245 0.6108 0.3314 0.022 Uiso 1 1 calc R . . . .
 C20 C 0.40609(17) 0.58780(6) 0.41797(8) 0.0175(3) Uani 1 1 d . . . . .
 H20A H 0.3546 0.5525 0.3854 0.026 Uiso 1 1 calc GR . . . .
 H20B H 0.5181 0.5744 0.4444 0.026 Uiso 1 1 calc GR . . . .
 H20C H 0.4264 0.6236 0.3798 0.026 Uiso 1 1 calc GR . . . .
 C18 C 0.33567(18) 0.70482(7) 0.64897(8) 0.0197(3) Uani 1 1 d . . . . .
 H18A H 0.3399 0.7462 0.6770 0.030 Uiso 1 1 calc GR . . . .
 H18B H 0.4249 0.6770 0.6750 0.030 Uiso 1 1 calc GR . . . .
 H18C H 0.2191 0.6860 0.6554 0.030 Uiso 1 1 calc GR . . . .
 C1 C 0.33236(17) 0.85550(6) 0.55707(9) 0.0171(3) Uani 1 1 d . . . . .
 C16 C 0.56799(17) 0.91567(6) 0.36300(9) 0.0186(3) Uani 1 1 d . . . . .
 H16 H 0.5558 0.9122 0.3030 0.022 Uiso 1 1 calc R . . . .
 C11 C 0.06033(18) 0.83841(6) 0.46905(9) 0.0198(3) Uani 1 1 d . . . . .
 H11 H 0.0467 0.8831 0.4700 0.024 Uiso 1 1 calc R . . . .
 C10 C -0.06265(17) 0.80210(6) 0.42712(9) 0.0193(3) Uani 1 1 d . . . . .
 H10 H -0.1632 0.8217 0.4015 0.023 Uiso 1 1 calc R . . . .
 C19 C 0.55082(17) 0.73595(7) 0.54206(9) 0.0192(3) Uani 1 1 d . . . . .
 H19A H 0.5624 0.7457 0.4816 0.029 Uiso 1 1 calc GR . . . .
 H19B H 0.6362 0.7032 0.5589 0.029 Uiso 1 1 calc GR . . . .
 H19C H 0.5730 0.7743 0.5757 0.029 Uiso 1 1 calc GR . . . .
 C21 C 0.24111(18) 0.55340(6) 0.54258(9) 0.0194(3) Uani 1 1 d . . . . .
 H21A H 0.1529 0.5667 0.5831 0.029 Uiso 1 1 calc GR . . . .
 H21B H 0.3481 0.5400 0.5736 0.029 Uiso 1 1 calc GR . . . .
 H21C H 0.1950 0.5180 0.5085 0.029 Uiso 1 1 calc GR . . . .
 C22 C 0.76626(19) 0.96040(7) 0.66507(9) 0.0235(3) Uani 1 1 d . . . . .
 H22A H 0.8748 0.9414 0.6448 0.035 Uiso 1 1 calc GR . . . .
 H22B H 0.7629 0.9564 0.7270 0.035 Uiso 1 1 calc GR . . . .
 H22C H 0.7625 1.0053 0.6493 0.035 Uiso 1 1 calc GR . . . .
 C23 C 0.8136(2) 0.98174(8) 0.26580(9) 0.0283(3) Uani 1 1 d . . . . .
 H23A H 0.9013 1.0101 0.2418 0.042 Uiso 1 1 calc GR . . . .
 H23B H 0.6960 0.9945 0.2456 0.042 Uiso 1 1 calc GR . . . .
 H23C H 0.8366 0.9382 0.2478 0.042 Uiso 1 1 calc GR . . . .
 C1S C -0.0996(2) 0.79280(8) 0.69696(10) 0.0300(3) Uani 1 1 d . . . . .
 H1SA H -0.0340 0.7560 0.6752 0.036 Uiso 1 1 calc R . . . .
 H1SB H -0.1600 0.8139 0.6482 0.036 Uiso 1 1 calc R . . . .
 C2S C -0.2321(2) 0.77085(9) 0.75884(11) 0.0354(4) Uani 1 1 d . . . . .
 H2SA H -0.3075 0.7385 0.7321 0.053 Uiso 1 1 calc GR . . . .
 H2SB H -0.3042 0.8068 0.7761 0.053 Uiso 1 1 calc GR . . . .
 H2SC H -0.1714 0.7528 0.8089 0.053 Uiso 1 1 calc GR . . . .
 B1 B 0.7808(2) 0.58997(7) 0.65435(10) 0.0188(3) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F3 B1 1.4038(17) . ?
 F4 B1 1.3862(18) . ?
 F2 B1 1.3827(18) . ?
 F1 B1 1.3961(17) . ?
 O1 C13 1.3623(16) . ?
 O1 C22 1.4419(16) . ?
 O2 C15 1.3650(16) . ?
 O2 C23 1.4327(18) . ?
 O1S H1S 0.8400 . ?
 O1S C1S 1.4197(17) . ?
 N3 H3 1.0000 . ?
 N3 C5 1.4743(15) . ?
 N3 C20 1.4954(16) . ?
 N3 C21 1.4932(16) . ?
 N2 C3 1.4620(15) . ?
 N2 C18 1.4868(16) . ?
 N2 C19 1.4809(16) . ?
 N1 H1 0.93(2) . ?
 N1 C1 1.2809(18) . ?
 C5 C4 1.4317(17) . ?
 C5 C6 1.3716(18) . ?
 C4 C3 1.4401(17) . ?
 C4 C9 1.4337(17) . ?
 C15 C14 1.3986(19) . ?
 C15 C16 1.3954(19) . ?
 C3 C2 1.3824(18) . ?
 C9 C8 1.4184(18) . ?
 C9 C10 1.4176(19) . ?
 C17 H17 0.9500 . ?
 C17 C12 1.4010(18) . ?
 C17 C16 1.3899(19) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.4092(18) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.3851(19) . ?
 C2 C1 1.5103(17) . ?
 C2 C11 1.4209(18) . ?
 C13 C12 1.4259(17) . ?
 C12 C1 1.4877(18) . ?
 C8 H8 0.9500 . ?
 C8 C7 1.367(2) . ?
 C7 H7 0.9500 . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C16 H16 0.9500 . ?
 C11 H11 0.9500 . ?
 C11 C10 1.3663(19) . ?
 C10 H10 0.9500 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 0.9800 . ?
 C1S H1SA 0.9900 . ?
 C1S H1SB 0.9900 . ?
 C1S C2S 1.495(2) . ?
 C2S H2SA 0.9800 . ?
 C2S H2SB 0.9800 . ?
 C2S H2SC 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C13 O1 C22 118.10(11) . . ?
 C15 O2 C23 117.23(11) . . ?
 C1S O1S H1S 109.5 . . ?
 C5 N3 H3 106.6 . . ?
 C5 N3 C20 112.18(9) . . ?
 C5 N3 C21 113.15(10) . . ?
 C20 N3 H3 106.6 . . ?
 C21 N3 H3 106.6 . . ?
 C21 N3 C20 111.31(10) . . ?
 C3 N2 C18 112.95(10) . . ?
 C3 N2 C19 116.04(10) . . ?
 C19 N2 C18 112.64(10) . . ?
 C1 N1 H1 112.7(12) . . ?
 C4 C5 N3 118.43(11) . . ?
 C6 C5 N3 119.03(11) . . ?
 C6 C5 C4 122.45(11) . . ?
 C5 C4 C3 125.38(11) . . ?
 C5 C4 C9 116.08(11) . . ?
 C9 C4 C3 118.48(11) . . ?
 O2 C15 C14 114.61(11) . . ?
 O2 C15 C16 124.72(12) . . ?
 C16 C15 C14 120.66(12) . . ?
 C4 C3 N2 116.49(11) . . ?
 C2 C3 N2 123.16(11) . . ?
 C2 C3 C4 120.35(11) . . ?
 C8 C9 C4 120.32(12) . . ?
 C10 C9 C4 119.33(11) . . ?
 C10 C9 C8 120.31(12) . . ?
 C12 C17 H17 118.4 . . ?
 C16 C17 H17 118.4 . . ?
 C16 C17 C12 123.29(12) . . ?
 C5 C6 H6 119.9 . . ?
 C5 C6 C7 120.16(12) . . ?
 C7 C6 H6 119.9 . . ?
 C15 C14 H14 119.9 . . ?
 C13 C14 C15 120.28(12) . . ?
 C13 C14 H14 119.9 . . ?
 C3 C2 C1 124.09(11) . . ?
 C3 C2 C11 119.85(12) . . ?
 C11 C2 C1 116.03(11) . . ?
 O1 C13 C14 122.46(12) . . ?
 O1 C13 C12 116.80(12) . . ?
 C14 C13 C12 120.74(12) . . ?
 C17 C12 C13 116.79(12) . . ?
 C17 C12 C1 120.20(11) . . ?
 C13 C12 C1 123.01(12) . . ?
 C9 C8 H8 119.5 . . ?
 C7 C8 C9 121.04(12) . . ?
 C7 C8 H8 119.5 . . ?
 C6 C7 H7 120.0 . . ?
 C8 C7 C6 119.91(12) . . ?
 C8 C7 H7 120.0 . . ?
 N3 C20 H20A 109.5 . . ?
 N3 C20 H20B 109.5 . . ?
 N3 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 N2 C18 H18A 109.5 . . ?
 N2 C18 H18B 109.5 . . ?
 N2 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 N1 C1 C2 116.00(12) . . ?
 N1 C1 C12 127.00(12) . . ?
 C12 C1 C2 116.88(11) . . ?
 C15 C16 H16 120.9 . . ?
 C17 C16 C15 118.22(12) . . ?
 C17 C16 H16 120.9 . . ?
 C2 C11 H11 119.4 . . ?
 C10 C11 C2 121.11(12) . . ?
 C10 C11 H11 119.4 . . ?
 C9 C10 H10 119.7 . . ?
 C11 C10 C9 120.70(12) . . ?
 C11 C10 H10 119.7 . . ?
 N2 C19 H19A 109.5 . . ?
 N2 C19 H19B 109.5 . . ?
 N2 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 N3 C21 H21A 109.5 . . ?
 N3 C21 H21B 109.5 . . ?
 N3 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 O1 C22 H22A 109.5 . . ?
 O1 C22 H22B 109.5 . . ?
 O1 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 O2 C23 H23A 109.5 . . ?
 O2 C23 H23B 109.5 . . ?
 O2 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?
 O1S C1S H1SA 109.7 . . ?
 O1S C1S H1SB 109.7 . . ?
 O1S C1S C2S 109.65(12) . . ?
 H1SA C1S H1SB 108.2 . . ?
 C2S C1S H1SA 109.7 . . ?
 C2S C1S H1SB 109.7 . . ?
 C1S C2S H2SA 109.5 . . ?
 C1S C2S H2SB 109.5 . . ?
 C1S C2S H2SC 109.5 . . ?
 H2SA C2S H2SB 109.5 . . ?
 H2SA C2S H2SC 109.5 . . ?
 H2SB C2S H2SC 109.5 . . ?
 F4 B1 F3 108.93(12) . . ?
 F4 B1 F1 109.80(12) . . ?
 F2 B1 F3 109.91(12) . . ?
 F2 B1 F4 110.31(12) . . ?
 F2 B1 F1 109.03(12) . . ?
 F1 B1 F3 108.85(12) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.223
_oxdiff_exptl_absorpt_empirical_full_min  0.716

data_6c
_audit_creation_date               2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           '2(B F4), C23 H29 N3 O2'
_chemical_formula_sum              'C23 H29 B2 F8 N3 O2'
_chemical_formula_weight           553.11
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     7.6816(3)
_cell_length_b                     12.3759(5)
_cell_length_c                     15.8693(5)
_cell_angle_alpha                  112.684(3)
_cell_angle_beta                   93.269(3)
_cell_angle_gamma                  93.060(3)
_cell_volume                       1385.01(9)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      11569
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        71.0070
_cell_measurement_theta_min        2.9630
_shelx_estimated_absorpt_T_max     0.817
_shelx_estimated_absorpt_T_min     0.750
_exptl_absorpt_coefficient_mu      1.051
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.56926
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_lustre       .
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.326
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               572
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.29
_exptl_crystal_size_mid            0.24
_exptl_crystal_size_min            0.2
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0364
_diffrn_reflns_av_unetI/netI       0.0193
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.990
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              27137
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.990
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           71.608
_diffrn_reflns_theta_min           3.029
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              HyPix3000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -101.00 -62.00   0.50    1.00    --  -41.10 -44.00 -34.00   78
  2  ω    -52.00   6.00   0.50    1.00    --  -41.10  44.00 116.00  116
  3  ω     -7.00  18.00   0.50    1.00    --   41.10 -44.00 -34.00   50
  4  ω     51.00 104.00   0.50    1.00    --   41.10  44.00 116.00  106
  5  ω     38.00 114.00   0.50    5.00    --  100.29 -44.00 -34.00  152
  6  ω     87.00 150.00   0.50    5.00    --  100.29  44.00 116.00  126
  7  ω    -50.00 -11.00   0.50    1.00    --  -41.10 138.00  90.00   78
  8  ω    -62.00 -22.00   0.50    1.00    --  -41.10 -65.00   0.00   80
  9  ω    -73.00  11.00   0.50    1.00    --  -41.10 104.00  90.00  168
 10  ω    -96.00 -71.00   0.50    1.00    --  -41.10 -65.00   0.00   50
 11  ω    -45.00  -7.00   0.50    1.00    --  -41.10  32.00 150.00   76
 12  ω    -73.00 -23.00   0.50    1.00    --  -41.10 -54.00-150.00  100
 13  ω    -95.00 -57.00   0.50    1.00    --  -41.10 138.00  90.00   76
 14  ω    -19.00  47.00   0.50    1.00    --   41.10 -43.00 120.00  132
 15  ω    -22.00  60.00   0.50    1.00    --   41.10 -65.00-150.00  164
 16  ω     52.00 105.00   0.50    1.00    --   41.10  32.00-120.00  106
 17  ω     31.00  67.00   0.50    1.00    --   41.10 -77.00 -90.00   72
 18  ω    -22.00  25.00   0.50    1.00    --   41.10 -77.00 -90.00   94
 19  ω     77.00 107.00   0.50    1.00    --   41.10  32.00   0.00   60
 20  ω     42.00  76.00   0.50    1.00    --   41.10-104.00  60.00   68
 21  ω     -9.00  17.00   0.50    1.00    --   41.10-104.00  60.00   52
 22  ω     49.00  74.00   0.50    1.00    --   41.10  32.00 -90.00   50
 23  ω     35.00  62.00   0.50    1.00    --   41.10  32.00   0.00   54
 24  ω    -18.00  59.00   0.50    1.00    --   41.10 -65.00 -60.00  154
 25  ω     35.00 110.00   0.50    5.00    --  100.29 -33.00-150.00  150
 26  ω     39.00  93.00   0.50    5.00    --  100.29-145.00  90.00  108
 27  ω     38.00 123.00   0.50    5.00    --  100.29-145.00   0.00  170
 28  ω     51.00 102.00   0.50    5.00    --  100.29 -33.00  60.00  102
 29  ω     47.00 114.00   0.50    5.00    --  100.29 -50.00  30.00  134
 30  ω     35.00  92.00   0.50    5.00    --  100.29 -96.00 -30.00  114
 31  ω     85.00 131.00   0.50    5.00    --  100.29-145.00 -30.00   92
 32  ω     61.00 113.00   0.50    5.00    --  100.29-117.00 150.00  104
 33  ω     42.00  96.00   0.50    5.00    --  100.29 -96.00  60.00  108
 34  ω    106.00 131.00   0.50    5.00    --  100.29-145.00  90.00   50
 35  ω     86.00 131.00   0.50    5.00    --  100.29 117.00  30.00   90
 36  ω    100.00 157.00   0.50    5.00    --  100.29  25.00 -90.00  114
 37  ω    116.00 155.00   0.50    5.00    --  100.29  96.00 120.00   78
 38  ω     88.00 138.00   0.50    5.00    --  100.29  42.00  60.00  100
 39  ω     97.00 136.00   0.50    5.00    --  100.29  25.00-120.00   78
 40  ω    117.00 157.00   0.50    5.00    --  100.29  59.00 120.00   80
 41  ω     31.00 106.00   0.50    5.00    --  100.29 -96.00   0.00  150
 42  ω     86.00 111.00   0.50    5.00    --  100.29  96.00 120.00   50
 43  ω    132.00 157.00   0.50    5.00    --  100.29 145.00-150.00   50
 44  ω     77.00 104.00   0.50    5.00    --  100.29 145.00-150.00   54
 45  ω     34.00  60.00   0.50    5.00    --  100.29 -87.00-180.00   52
 46  ω    128.00 157.00   0.50    5.00    --  100.29  25.00  30.00   58
 47  ω     38.00 107.00   0.50    5.00    --  100.29 -50.00-180.00  138
 48  ω     94.00 119.00   0.50    5.00    --  100.29  25.00  30.00   50
 49  ω     50.00 109.00   0.50    5.00    --  100.29 -59.00 150.00  118
 50  ω    104.00 157.00   0.50    5.00    --  100.29  33.00-180.00  106
 51  ω     35.00 105.00   0.50    5.00    --  100.29 -25.00 120.00  140
 52  ω     97.00 124.00   0.50    5.00    --  100.29  42.00   0.00   54
 53  ω     35.00 115.00   0.50    5.00    --  100.29 -87.00 150.00  160
 54  ω     42.00  67.00   0.50    1.00    --   41.10  44.00 116.00   50
 55  ω    -54.00 -29.00   0.50    1.00    --    4.00 141.00  95.77   50
 56  ω    -36.00 -11.00   0.50    1.00    --   12.00 125.00-107.98   50
 57  ω    -12.00  13.00   0.50    1.00    --   24.00 104.00  70.99   50
 58  ω     -2.00  23.00   0.50    1.00    --   28.00  93.00 -10.24   50
 59  ω     -2.00  23.00   0.50    1.00    --   28.00  93.00-126.21   50
 60  ω      2.00  27.00   0.50    1.00    --   32.00  91.00  35.60   50
 61  ω      4.00  29.00   0.50    1.00    --   32.00  88.00-142.58   50
 62  ω      4.00  29.00   0.50    1.00    --   32.00  88.00 -68.87   50
 63  ω      3.00  28.00   0.50    1.00    --   32.00  89.00 117.36   50
 64  ω      2.00  27.00   0.50    1.00    --   32.00  91.00 165.79   50
 65  ω      4.00  29.00   0.50    1.00    --   32.00  87.00  62.73   50
 66  ω      9.00  34.00   0.50    1.00    --   36.00  85.00 -30.81   50
 67  ω     14.00  39.00   0.50    1.00    --   40.00  82.00 125.95   50
 68  ω     15.00  40.00   0.50    1.00    --   40.00  79.00  67.35   50
 69  ω     19.00  44.00   0.50    1.00    --   44.00  80.00 162.54   50
 70  ω     19.00  44.00   0.50    1.00    --   44.00  80.00  -0.43   50
 71  ω     19.00  45.00   0.50    1.00    --   44.00  82.00-152.35   52
 72  ω     19.00  44.00   0.50    1.00    --   44.00  80.00-164.53   50
 73  ω     19.00  44.00   0.50    1.00    --   44.00  79.00 -44.41   50
 74  ω     19.00  44.00   0.50    1.00    --   44.00  80.00  91.97   50
 75  ω     18.00  43.00   0.50    1.00    --   44.00  82.00  28.64   50
 76  ω     64.00 100.00   0.50    1.00    --   48.00  77.00 -76.42   72
 77  ω     24.00  58.00   0.50    1.00    --   48.00  77.00 -76.42   68
 78  ω     27.00  53.00   0.50    1.00    --   52.00  77.00  71.56   52
 79  ω     27.00  54.00   0.50    1.00    --   52.00  76.00  37.72   54
 80  ω     32.00  58.00   0.50    1.00    --   56.00  75.00-113.72   52
 81  ω     32.00  59.00   0.50    1.00    --   56.00  76.00 -13.43   54
 82  ω     31.00  58.00   0.50    1.00    --   56.00  77.00 160.36   54
 83  ω     32.00  59.00   0.50    1.00    --   56.00  75.00 135.49   54
 84  ω     34.00  59.00   0.50    1.00    --   56.00  73.00 108.83   50
 85  ω     77.00 105.00   0.50    1.00    --   56.00  75.00 135.49   56
 86  ω     40.00  75.00   0.50    1.00    --   64.00  75.00 155.32   70
 87  ω     40.00  70.00   0.50    1.00    --   64.00  76.00-161.89   60
 88  ω     43.00  70.00   0.50    1.00    --   64.00  71.00 115.12   54
 89  ω     45.00  72.00   0.50    1.00    --   68.00  77.00 -12.45   54
 90  ω     81.00 108.00   0.50    1.00    --   68.00  77.00 -12.45   54
 91  ω     43.00  86.00   0.50    1.00    --   68.00  77.00  32.06   86
 92  ω     49.00  74.00   0.50    1.00    --   68.00  64.00-127.46   50
 93  ω     45.00  81.00   0.50    1.00    --   68.00  77.00-107.13   72
 94  ω     48.00  86.00   0.50    5.00    --   72.00  77.00 -90.36   76
 95  ω     47.00  79.00   0.50    5.00    --   72.00  77.00 -59.46   64
 96  ω     51.00  87.00   0.50    5.00    --   72.00  72.00-128.39   72
 97  ω     54.00  91.00   0.50    5.00    --   76.00  71.00 163.03   74
 98  ω     57.00  93.00   0.50    5.00    --   80.00  72.00 -67.64   72
 99  ω     57.00  92.00   0.50    5.00    --   80.00  73.00  -9.00   70
100  ω     57.00  85.00   0.50    5.00    --   80.00  73.00 116.35   56
101  ω     55.00  93.00   0.50    5.00    --   80.00  77.00  48.02   76
102  ω     63.00  97.00   0.50    5.00    --   84.00  77.00  51.83   68
103  ω     76.00 102.00   0.50    5.00    --  100.29  77.00 -60.00   52
104  ω    121.00 148.00   0.50    5.00    --  100.29  59.00  90.00   54
105  ω     75.00 149.00   0.50    5.00    --  100.29  77.00 -90.00  148
106  ω    123.00 150.00   0.50    5.00    --  100.29  77.00-180.00   54
107  ω     76.00 112.00   0.50    5.00    --  100.29  77.00-180.00   72
108  ω    132.00 157.00   0.50    5.00    --  100.29  77.00-150.00   50
109  ω     82.00 136.00   0.50    5.00    --  100.29  59.00 -30.00  108
110  ω    124.00 151.00   0.50    5.00    --  100.29  59.00-150.00   54
111  ω     77.00 113.00   0.50    5.00    --  100.29  77.00-150.00   72
112  ω     82.00 109.00   0.50    5.00    --  100.29  59.00  90.00   54
113  ω     75.00 102.00   0.50    5.00    --  100.29  77.00  30.00   54
114  ω    126.00 153.00   0.50    5.00    --  100.29  77.00-120.00   54
115  ω     75.00 116.00   0.50    5.00    --  100.29  77.00-120.00   82
116  ω     82.00 109.00   0.50    5.00    --  100.29  59.00-150.00   54
117  ω    119.00 150.00   0.50    5.00    --  100.29  77.00 150.00   62
118  ω     75.00 101.00   0.50    5.00    --  100.29  77.00 150.00   52
119  ω     85.00 110.00   0.50    5.00    --  100.29 -33.00   0.00   50
120  ω    110.00 150.00   0.50    5.00    --  100.29  68.00   0.00   80
121  ω    115.00 152.00   0.50    5.00    --  100.29  77.00  60.00   74
122  ω     38.00  65.00   0.50    5.00    --  100.29 -33.00   0.00   54
123  ω     80.00 107.00   0.50    5.00    --  100.29  68.00   0.00   54
124  ω     75.00 108.00   0.50    5.00    --  100.29  77.00  90.00   66
125  ω     82.00 121.00   0.50    5.00    --  100.29  59.00-180.00   78
126  ω     77.00 104.00   0.50    5.00    --  100.29  77.00  60.00   54
127  ω     76.00 104.00   0.50    5.00    --  100.29  77.00   0.00   56
128  ω     77.00 112.00   0.50    5.00    --  100.29  77.00 120.00   70
129  ω     79.00 106.00   0.50    5.00    --  100.29  68.00-150.00   54
130  ω    120.00 150.00   0.50    5.00    --  100.29  77.00 -30.00   60
131  ω    127.00 156.00   0.50    5.00    --  100.29  68.00  30.00   58
132  ω     75.00 101.00   0.50    5.00    --  100.29  77.00 -30.00   52
133  ω    112.00 156.00   0.50    5.00    --  100.29  50.00 -60.00   88
134  ω     80.00 105.00   0.50    5.00    --  100.29  68.00  30.00   50
135  ω    112.00 149.00   0.50    5.00    --  100.29  77.00 -60.00   74
136  ω     40.00  65.00   0.50    1.00    --   41.10  54.00 -90.00   50
137  ω     19.00  44.00   0.50    1.00    --   44.00  81.00-114.01   50
138  ω     51.00  76.00   0.50    5.00    --   72.00  70.00 109.03   50
139  ω     57.00  84.00   0.50    5.00    --   80.00  72.00-175.69   54
140  ω     58.00  85.00   0.50    5.00    --   80.00  74.00 -33.30   54
141  ω     60.00  87.00   0.50    5.00    --   84.00  76.00  -4.01   54
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type   
 'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.1662469000
_diffrn_orient_matrix_UB_12        0.0829179000
_diffrn_orient_matrix_UB_13        0.0434655000
_diffrn_orient_matrix_UB_21        0.0685095000
_diffrn_orient_matrix_UB_22        -0.0883259000
_diffrn_orient_matrix_UB_23        0.0381368000
_diffrn_orient_matrix_UB_31        0.0910604000
_diffrn_orient_matrix_UB_32        -0.0604046000
_diffrn_orient_matrix_UB_33        -0.0883498000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4668
_reflns_number_total               5370
_reflns_odcompleteness_completeness  99.91
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       69.95
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection         'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction          'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.423
_refine_diff_density_min           -0.326
_refine_diff_density_rms           0.044
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       349
_refine_ls_number_reflns           5370
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0533
_refine_ls_R_factor_gt             0.0482
_refine_ls_restrained_S_all        1.084
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0740P)²+0.5012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1371
_refine_ls_wR_factor_ref           0.1415
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C16(H16), C11(H11), C10(H10), C8(H8), C7(H7), C6(H6)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F6 F 0.47572(13) 1.04407(10) 0.34633(8) 0.0507(3) Uani 1 1 d . . . . .
 F3 F 1.05561(14) 0.42546(11) 0.24849(7) 0.0537(3) Uani 1 1 d . . . . .
 F8 F 0.33523(15) 0.94147(11) 0.41807(8) 0.0540(3) Uani 1 1 d . . . . .
 F7 F 0.18012(14) 1.03778(11) 0.34711(9) 0.0582(3) Uani 1 1 d . . . . .
 O2 O 0.85102(16) 0.33705(11) 0.50408(8) 0.0433(3) Uani 1 1 d . . . . .
 O1 O 0.64412(16) 0.71422(11) 0.59387(7) 0.0402(3) Uani 1 1 d . . . . .
 F4 F 0.81148(16) 0.30742(14) 0.17442(8) 0.0699(4) Uani 1 1 d . . . . .
 F5 F 0.3102(2) 0.87453(12) 0.26325(9) 0.0716(4) Uani 1 1 d . . . . .
 F1 F 1.0757(2) 0.26299(15) 0.11918(9) 0.0764(4) Uani 1 1 d . . . . .
 F2 F 0.94763(19) 0.42003(15) 0.11065(9) 0.0772(4) Uani 1 1 d . . . . .
 N2 N 0.82461(17) 0.78241(13) 0.30218(9) 0.0361(3) Uani 1 1 d . . . . .
 N1 N 0.52870(18) 0.78630(13) 0.46758(10) 0.0403(3) Uani 1 1 d . . . . .
 H1A H 0.5364 0.8002 0.5265 0.048 Uiso 1 1 calc R . . . .
 H1B H 0.4840 0.8373 0.4480 0.048 Uiso 1 1 calc R . . . .
 N3 N 0.8606(2) 0.82097(19) 0.15444(11) 0.0580(5) Uani 1 1 d . . . . .
 H3 H 0.8830 0.8206 0.2170 0.070 Uiso 1 1 calc R . . . .
 C17 C 0.7028(2) 0.49755(16) 0.36627(11) 0.0361(4) Uani 1 1 d . . . . .
 H17 H 0.6882 0.4893 0.3042 0.043 Uiso 1 1 calc R . . . .
 C12 C 0.65801(19) 0.60250(15) 0.43527(11) 0.0350(4) Uani 1 1 d . . . . .
 C15 C 0.7927(2) 0.42017(15) 0.47701(11) 0.0363(4) Uani 1 1 d . . . . .
 C14 C 0.7573(2) 0.52467(16) 0.54815(11) 0.0368(4) Uani 1 1 d . . . . .
 H14 H 0.7809 0.5342 0.6101 0.044 Uiso 1 1 calc R . . . .
 C2 C 0.5491(2) 0.67062(15) 0.30975(11) 0.0360(4) Uani 1 1 d . . . . .
 C1 C 0.5837(2) 0.68991(15) 0.40920(11) 0.0358(4) Uani 1 1 d . . . . .
 C16 C 0.7663(2) 0.40737(16) 0.38507(11) 0.0370(4) Uani 1 1 d . . . . .
 H16 H 0.7922 0.3372 0.3368 0.044 Uiso 1 1 calc R . . . .
 C13 C 0.6886(2) 0.61313(15) 0.52848(11) 0.0352(4) Uani 1 1 d . . . . .
 C4 C 0.6011(2) 0.70153(16) 0.17028(11) 0.0376(4) Uani 1 1 d . . . . .
 C9 C 0.4402(2) 0.63296(16) 0.12812(11) 0.0391(4) Uani 1 1 d . . . . .
 C3 C 0.6552(2) 0.71812(16) 0.26359(11) 0.0359(4) Uani 1 1 d . . . . .
 C11 C 0.3908(2) 0.60172(16) 0.26627(12) 0.0397(4) Uani 1 1 d . . . . .
 H11 H 0.3202 0.5689 0.2991 0.048 Uiso 1 1 calc R . . . .
 C5 C 0.6937(2) 0.74963(18) 0.11547(12) 0.0433(4) Uani 1 1 d . . . . .
 C10 C 0.3401(2) 0.58261(16) 0.17720(12) 0.0414(4) Uani 1 1 d . . . . .
 H10 H 0.2357 0.5347 0.1482 0.050 Uiso 1 1 calc R . . . .
 C8 C 0.3798(2) 0.61734(17) 0.03721(11) 0.0443(4) Uani 1 1 d . . . . .
 H8 H 0.2729 0.5717 0.0100 0.053 Uiso 1 1 calc R . . . .
 C7 C 0.4724(3) 0.66663(19) -0.01114(12) 0.0491(5) Uani 1 1 d . . . . .
 H7 H 0.4293 0.6563 -0.0713 0.059 Uiso 1 1 calc R . . . .
 C6 C 0.6320(2) 0.73287(19) 0.02787(12) 0.0479(5) Uani 1 1 d . . . . .
 H6 H 0.6976 0.7662 -0.0064 0.057 Uiso 1 1 calc R . . . .
 C19 C 0.9601(2) 0.70675(19) 0.31258(15) 0.0494(5) Uani 1 1 d . . . . .
 H19A H 0.9391 0.6861 0.3651 0.074 Uiso 1 1 calc GR . . . .
 H19B H 1.0759 0.7491 0.3227 0.074 Uiso 1 1 calc GR . . . .
 H19C H 0.9551 0.6349 0.2568 0.074 Uiso 1 1 calc GR . . . .
 C23 C 0.8780(3) 0.22433(17) 0.43450(13) 0.0475(4) Uani 1 1 d . . . . .
 H23A H 0.7701 0.1924 0.3943 0.071 Uiso 1 1 calc GR . . . .
 H23B H 0.9097 0.1704 0.4636 0.071 Uiso 1 1 calc GR . . . .
 H23C H 0.9725 0.2335 0.3983 0.071 Uiso 1 1 calc GR . . . .
 C22 C 0.6781(3) 0.73268(18) 0.68928(11) 0.0452(4) Uani 1 1 d . . . . .
 H22A H 0.6138 0.6702 0.7012 0.068 Uiso 1 1 calc GR . . . .
 H22B H 0.6397 0.8090 0.7281 0.068 Uiso 1 1 calc GR . . . .
 H22C H 0.8037 0.7313 0.7031 0.068 Uiso 1 1 calc GR . . . .
 C18 C 0.8260(2) 0.89235(19) 0.38437(14) 0.0518(5) Uani 1 1 d . . . . .
 H18A H 0.7268 0.9359 0.3776 0.078 Uiso 1 1 calc GR . . . .
 H18B H 0.9355 0.9405 0.3914 0.078 Uiso 1 1 calc GR . . . .
 H18C H 0.8165 0.8736 0.4387 0.078 Uiso 1 1 calc GR . . . .
 B2 B 0.3243(3) 0.97422(19) 0.34203(14) 0.0411(4) Uani 1 1 d . . . . .
 B1 B 0.9718(3) 0.3530(2) 0.16298(14) 0.0498(5) Uani 1 1 d . . . . .
 C21 C 1.0094(3) 0.7649(4) 0.10201(16) 0.1214(17) Uani 1 1 d . . . . .
 H21A H 1.0074 0.6828 0.0955 0.182 Uiso 1 1 calc GR . . . .
 H21B H 1.1201 0.8071 0.1350 0.182 Uiso 1 1 calc GR . . . .
 H21C H 0.9984 0.7680 0.0412 0.182 Uiso 1 1 calc GR . . . .
 C20 C 0.8479(5) 0.9472(3) 0.1684(2) 0.1055(13) Uani 1 1 d . . . . .
 H20A H 0.8276 0.9529 0.1087 0.158 Uiso 1 1 calc GR . . . .
 H20B H 0.9572 0.9931 0.1999 0.158 Uiso 1 1 calc GR . . . .
 H20C H 0.7505 0.9781 0.2055 0.158 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F6 B2 1.394(2) . ?
 F3 B1 1.400(2) . ?
 F8 B2 1.413(2) . ?
 F7 B2 1.381(2) . ?
 O2 C15 1.346(2) . ?
 O2 C23 1.441(2) . ?
 O1 C13 1.358(2) . ?
 O1 C22 1.4471(19) . ?
 F4 B1 1.378(3) . ?
 F5 B2 1.370(2) . ?
 F1 B1 1.387(3) . ?
 F2 B1 1.393(3) . ?
 N2 C3 1.458(2) . ?
 N2 C19 1.480(2) . ?
 N2 C18 1.477(2) . ?
 N1 H1A 0.8800 . ?
 N1 H1B 0.8800 . ?
 N1 C1 1.306(2) . ?
 N3 H3 1.0000 . ?
 N3 C5 1.474(2) . ?
 N3 C21 1.493(3) . ?
 N3 C20 1.501(4) . ?
 C17 H17 0.9500 . ?
 C17 C12 1.414(2) . ?
 C17 C16 1.368(3) . ?
 C12 C1 1.432(2) . ?
 C12 C13 1.438(2) . ?
 C15 C14 1.403(2) . ?
 C15 C16 1.407(2) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.371(3) . ?
 C2 C1 1.508(2) . ?
 C2 C3 1.376(3) . ?
 C2 C11 1.422(2) . ?
 C16 H16 0.9500 . ?
 C4 C9 1.432(2) . ?
 C4 C3 1.447(2) . ?
 C4 C5 1.429(3) . ?
 C9 C10 1.407(3) . ?
 C9 C8 1.426(2) . ?
 C11 H11 0.9500 . ?
 C11 C10 1.369(2) . ?
 C5 C6 1.376(2) . ?
 C10 H10 0.9500 . ?
 C8 H8 0.9500 . ?
 C8 C7 1.358(3) . ?
 C7 H7 0.9500 . ?
 C7 C6 1.405(3) . ?
 C6 H6 0.9500 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 0.9800 . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C15 O2 C23 118.12(13) . . ?
 C13 O1 C22 118.80(14) . . ?
 C3 N2 C19 113.31(14) . . ?
 C3 N2 C18 117.11(13) . . ?
 C18 N2 C19 111.93(15) . . ?
 H1A N1 H1B 120.0 . . ?
 C1 N1 H1A 120.0 . . ?
 C1 N1 H1B 120.0 . . ?
 C5 N3 H3 106.0 . . ?
 C5 N3 C21 111.3(2) . . ?
 C5 N3 C20 111.98(18) . . ?
 C21 N3 H3 106.0 . . ?
 C21 N3 C20 114.7(3) . . ?
 C20 N3 H3 106.0 . . ?
 C12 C17 H17 118.6 . . ?
 C16 C17 H17 118.6 . . ?
 C16 C17 C12 122.82(15) . . ?
 C17 C12 C1 119.14(14) . . ?
 C17 C12 C13 116.71(15) . . ?
 C1 C12 C13 124.14(15) . . ?
 O2 C15 C14 115.13(14) . . ?
 O2 C15 C16 124.49(16) . . ?
 C14 C15 C16 120.38(16) . . ?
 C15 C14 H14 119.9 . . ?
 C13 C14 C15 120.19(15) . . ?
 C13 C14 H14 119.9 . . ?
 C3 C2 C1 124.35(15) . . ?
 C3 C2 C11 121.22(15) . . ?
 C11 C2 C1 114.39(15) . . ?
 N1 C1 C12 123.52(15) . . ?
 N1 C1 C2 115.13(15) . . ?
 C12 C1 C2 121.15(14) . . ?
 C17 C16 C15 118.93(16) . . ?
 C17 C16 H16 120.5 . . ?
 C15 C16 H16 120.5 . . ?
 O1 C13 C12 115.95(15) . . ?
 O1 C13 C14 123.17(14) . . ?
 C14 C13 C12 120.87(15) . . ?
 C9 C4 C3 118.48(16) . . ?
 C5 C4 C9 115.96(15) . . ?
 C5 C4 C3 125.55(16) . . ?
 C10 C9 C4 119.84(15) . . ?
 C10 C9 C8 119.93(16) . . ?
 C8 C9 C4 120.23(17) . . ?
 C2 C3 N2 123.78(14) . . ?
 C2 C3 C4 119.38(15) . . ?
 C4 C3 N2 116.82(15) . . ?
 C2 C11 H11 119.9 . . ?
 C10 C11 C2 120.12(17) . . ?
 C10 C11 H11 119.9 . . ?
 C4 C5 N3 118.90(14) . . ?
 C6 C5 N3 118.67(18) . . ?
 C6 C5 C4 122.43(18) . . ?
 C9 C10 H10 119.5 . . ?
 C11 C10 C9 120.91(16) . . ?
 C11 C10 H10 119.5 . . ?
 C9 C8 H8 119.4 . . ?
 C7 C8 C9 121.15(17) . . ?
 C7 C8 H8 119.4 . . ?
 C8 C7 H7 120.0 . . ?
 C8 C7 C6 119.93(16) . . ?
 C6 C7 H7 120.0 . . ?
 C5 C6 C7 120.29(19) . . ?
 C5 C6 H6 119.9 . . ?
 C7 C6 H6 119.9 . . ?
 N2 C19 H19A 109.5 . . ?
 N2 C19 H19B 109.5 . . ?
 N2 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 O2 C23 H23A 109.5 . . ?
 O2 C23 H23B 109.5 . . ?
 O2 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?
 O1 C22 H22A 109.5 . . ?
 O1 C22 H22B 109.5 . . ?
 O1 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 N2 C18 H18A 109.5 . . ?
 N2 C18 H18B 109.5 . . ?
 N2 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 F6 B2 F8 108.39(14) . . ?
 F7 B2 F6 109.71(16) . . ?
 F7 B2 F8 108.51(16) . . ?
 F5 B2 F6 110.34(16) . . ?
 F5 B2 F8 108.75(17) . . ?
 F5 B2 F7 111.07(15) . . ?
 F4 B1 F3 109.78(16) . . ?
 F4 B1 F1 110.2(2) . . ?
 F4 B1 F2 109.35(17) . . ?
 F1 B1 F3 109.28(16) . . ?
 F1 B1 F2 109.52(17) . . ?
 F2 B1 F3 108.7(2) . . ?
 N3 C21 H21A 109.5 . . ?
 N3 C21 H21B 109.5 . . ?
 N3 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 N3 C20 H20A 109.5 . . ?
 N3 C20 H20B 109.5 . . ?
 N3 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.669
_oxdiff_exptl_absorpt_empirical_full_min  0.467

 
data_4a.HClO4
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 '(C22 H26 N3 O)+, (Cl O4)-' 
_chemical_formula_sum 
 'C22 H26 Cl N3 O5' 
_chemical_formula_weight          447.91 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            'Monoclinic'
_symmetry_space_group_name_H-M    'P 21/c  '
_symmetry_space_group_name_Hall   '-P 2ybc' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    7.7872(7) 
_cell_length_b                    14.0217(12) 
_cell_length_c                    20.1562(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.971(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2192.6(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     6131
_cell_measurement_theta_min       2.63
_cell_measurement_theta_max       29.19
 
_exptl_crystal_description        'prizm'
_exptl_crystal_colour             'light-yellow'
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.357 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              944 
_exptl_absorpt_coefficient_mu     0.213 
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0
_diffrn_reflns_number             26618 
_diffrn_reflns_av_R_equivalents   0.0602 
_diffrn_reflns_av_sigmaI/netI     0.0498 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        27 
_diffrn_reflns_theta_min          2.03 
_diffrn_reflns_theta_max          29.34 
_reflns_number_total              5961 
_reflns_number_gt                 4424 
_reflns_threshold_expression      'I>2σ(I)'
  
_computing_data_collection        'APEX (Bruker, 2009)' 
_computing_cell_refinement        'SAINT (Bruker, 2009)' 
_computing_data_reduction         'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material   
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0561P)²+1.7420P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5961 
_refine_ls_number_parameters      302 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0826 
_refine_ls_R_factor_gt            0.0560 
_refine_ls_wR_factor_ref          0.1389 
_refine_ls_wR_factor_gt           0.1266 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.039 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O -0.4531(2) 0.66171(11) 0.02944(8) 0.0309(4) Uani 1 1 d . . . 
N1 N 0.19065(19) 0.41801(11) 0.26709(8) 0.0178(3) Uani 1 1 d . . . 
N2 N 0.2427(2) 0.43086(12) 0.39427(8) 0.0197(3) Uani 1 1 d . . . 
H2 H 0.2446 0.4341 0.3497 0.024 Uiso 1 1 d R . . 
N3 N 0.0442(2) 0.31317(15) 0.11438(9) 0.0316(4) Uani 1 1 d . . . 
H3 H 0.097(4) 0.267(2) 0.1389(14) 0.044(8) Uiso 1 1 d . . . 
C1 C 0.0309(2) 0.36580(13) 0.27342(9) 0.0157(4) Uani 1 1 d . . . 
C2 C -0.0050(2) 0.33959(13) 0.33972(10) 0.0168(4) Uani 1 1 d . . . 
C3 C 0.0940(2) 0.36753(14) 0.39918(10) 0.0196(4) Uani 1 1 d . . . 
C4 C 0.0535(3) 0.33890(16) 0.46079(11) 0.0267(4) Uani 1 1 d . . . 
H4A H 0.1227 0.3589 0.4994 0.032 Uiso 1 1 calc R . . 
C5 C -0.0905(3) 0.27986(16) 0.46708(11) 0.0296(5) Uani 1 1 d . . . 
H5A H -0.1175 0.2593 0.5099 0.036 Uiso 1 1 calc R . . 
C6 C -0.1910(3) 0.25228(15) 0.41176(11) 0.0267(4) Uani 1 1 d . . . 
H6A H -0.2887 0.2130 0.4164 0.032 Uiso 1 1 calc R . . 
C7 C -0.1524(2) 0.28105(13) 0.34763(10) 0.0204(4) Uani 1 1 d . . . 
C8 C -0.2604(2) 0.25452(14) 0.29079(11) 0.0239(4) Uani 1 1 d . . . 
H8A H -0.3579 0.2154 0.2959 0.029 Uiso 1 1 calc R . . 
C9 C -0.2274(2) 0.28389(15) 0.22909(11) 0.0237(4) Uani 1 1 d . . . 
H9A H -0.3043 0.2670 0.1918 0.028 Uiso 1 1 calc R . . 
C10 C -0.0796(2) 0.33951(13) 0.21955(10) 0.0181(4) Uani 1 1 d . . . 
C11 C -0.0530(2) 0.36249(14) 0.14836(10) 0.0209(4) Uani 1 1 d . . . 
C12 C -0.1576(2) 0.44128(14) 0.11654(10) 0.0192(4) Uani 1 1 d . . . 
C13 C -0.1567(2) 0.45785(14) 0.04853(10) 0.0208(4) Uani 1 1 d . . . 
H13A H -0.0883 0.4185 0.0229 0.025 Uiso 1 1 calc R . . 
C14 C -0.2536(3) 0.53055(15) 0.01734(11) 0.0225(4) Uani 1 1 d . . . 
H14A H -0.2519 0.5408 -0.0292 0.027 Uiso 1 1 calc R . . 
C15 C -0.3533(3) 0.58826(15) 0.05493(11) 0.0239(4) Uani 1 1 d . . . 
C16 C -0.3553(3) 0.57270(16) 0.12279(11) 0.0293(5) Uani 1 1 d . . . 
H16A H -0.4233 0.6124 0.1483 0.035 Uiso 1 1 calc R . . 
C17 C -0.2587(3) 0.49979(16) 0.15350(11) 0.0253(4) Uani 1 1 d . . . 
H17A H -0.2612 0.4895 0.2000 0.030 Uiso 1 1 calc R . . 
C18 C 0.3281(3) 0.35820(17) 0.24166(12) 0.0288(5) Uani 1 1 d . . . 
H18A H 0.3300 0.2957 0.2635 0.043 Uiso 1 1 calc R . . 
H18B H 0.4400 0.3895 0.2513 0.043 Uiso 1 1 calc R . . 
H18C H 0.3049 0.3499 0.1934 0.043 Uiso 1 1 calc R . . 
C19 C 0.1732(3) 0.51109(15) 0.23277(11) 0.0261(4) Uani 1 1 d . . . 
H19A H 0.0771 0.5466 0.2491 0.039 Uiso 1 1 calc R . . 
H19B H 0.1510 0.5007 0.1847 0.039 Uiso 1 1 calc R . . 
H19C H 0.2800 0.5476 0.2417 0.039 Uiso 1 1 calc R . . 
C20 C 0.4068(3) 0.38897(17) 0.42528(12) 0.0305(5) Uani 1 1 d . . . 
H20A H 0.4221 0.3248 0.4074 0.046 Uiso 1 1 calc R . . 
H20B H 0.4022 0.3852 0.4736 0.046 Uiso 1 1 calc R . . 
H20C H 0.5039 0.4294 0.4152 0.046 Uiso 1 1 calc R . . 
C21 C 0.2126(3) 0.52799(15) 0.42040(11) 0.0286(5) Uani 1 1 d . . . 
H21A H 0.1051 0.5537 0.3986 0.043 Uiso 1 1 calc R . . 
H21B H 0.3088 0.5697 0.4112 0.043 Uiso 1 1 calc R . . 
H21C H 0.2042 0.5246 0.4686 0.043 Uiso 1 1 calc R . . 
C22 C -0.4504(3) 0.68203(17) -0.04002(11) 0.0301(5) Uani 1 1 d . . . 
H22A H -0.5239 0.7373 -0.0516 0.045 Uiso 1 1 calc R . . 
H22B H -0.4935 0.6267 -0.0661 0.045 Uiso 1 1 calc R . . 
H22C H -0.3320 0.6960 -0.0499 0.045 Uiso 1 1 calc R . . 
Cl1 Cl 0.32075(6) 0.08742(3) 0.15904(2) 0.02039(12) Uani 1 1 d D . . 
O1S O 0.1666(2) 0.11717(15) 0.18614(11) 0.0536(6) Uani 1 1 d . A . 
O2S O 0.3964(8) 0.0061(3) 0.19111(17) 0.0640(15) Uani 0.847(11) 1 d P A 1 
O3S O 0.2849(7) 0.0678(4) 0.09025(12) 0.0758(16) Uani 0.847(11) 1 d P A 1 
O4S O 0.4411(4) 0.1624(3) 0.1644(4) 0.090(2) Uani 0.847(11) 1 d P A 1 
O2S' O 0.3184(19) -0.0086(9) 0.1780(6) 0.018(3) Uiso 0.153(11) 1 d P A 2 
O3S' O 0.353(3) 0.0923(14) 0.0914(4) 0.048(5) Uiso 0.153(11) 1 d PD A 2 
O4S' O 0.442(2) 0.1327(12) 0.2038(9) 0.045(5) Uiso 0.153(11) 1 d P A 2 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C15 1.363(2) . ? 
O1 C22 1.431(3) . ? 
N1 C1 1.458(2) . ? 
N1 C19 1.478(3) . ? 
N1 C18 1.485(3) . ? 
N2 C3 1.469(2) . ? 
N2 C21 1.486(3) . ? 
N2 C20 1.493(3) . ? 
N2 H2 0.9000 . ? 
N3 C11 1.269(3) . ? 
N3 H3 0.90(3) . ? 
C1 C10 1.376(3) . ? 
C1 C2 1.436(3) . ? 
C2 C3 1.423(3) . ? 
C2 C7 1.431(3) . ? 
C3 C4 1.368(3) . ? 
C4 C5 1.409(3) . ? 
C4 H4A 0.9500 . ? 
C5 C6 1.362(3) . ? 
C5 H5A 0.9500 . ? 
C6 C7 1.411(3) . ? 
C6 H6A 0.9500 . ? 
C7 C8 1.411(3) . ? 
C8 C9 1.356(3) . ? 
C8 H8A 0.9500 . ? 
C9 C10 1.417(3) . ? 
C9 H9A 0.9500 . ? 
C10 C11 1.502(3) . ? 
C11 C12 1.485(3) . ? 
C12 C13 1.391(3) . ? 
C12 C17 1.396(3) . ? 
C13 C14 1.386(3) . ? 
C13 H13A 0.9500 . ? 
C14 C15 1.391(3) . ? 
C14 H14A 0.9500 . ? 
C15 C16 1.386(3) . ? 
C16 C17 1.383(3) . ? 
C16 H16A 0.9500 . ? 
C17 H17A 0.9500 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
C21 H21A 0.9800 . ? 
C21 H21B 0.9800 . ? 
C21 H21C 0.9800 . ? 
C22 H22A 0.9800 . ? 
C22 H22B 0.9800 . ? 
C22 H22C 0.9800 . ? 
Cl1 O2S' 1.400(13) . ? 
Cl1 O4S' 1.402(15) . ? 
Cl1 O4S 1.407(3) . ? 
Cl1 O3S' 1.409(5) . ? 
Cl1 O2S 1.414(2) . ? 
Cl1 O3S 1.417(3) . ? 
Cl1 O1S 1.4239(18) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C15 O1 C22 117.59(16) . . ? 
C1 N1 C19 116.10(15) . . ? 
C1 N1 C18 113.09(15) . . ? 
C19 N1 C18 112.13(16) . . ? 
C3 N2 C21 112.37(16) . . ? 
C3 N2 C20 112.64(16) . . ? 
C21 N2 C20 111.57(17) . . ? 
C3 N2 H2 100.3 . . ? 
C21 N2 H2 108.9 . . ? 
C20 N2 H2 110.5 . . ? 
C11 N3 H3 111.5(18) . . ? 
C10 C1 C2 120.45(16) . . ? 
C10 C1 N1 123.04(17) . . ? 
C2 C1 N1 116.48(16) . . ? 
C3 C2 C7 116.45(17) . . ? 
C3 C2 C1 125.34(16) . . ? 
C7 C2 C1 118.21(17) . . ? 
C4 C3 C2 122.22(18) . . ? 
C4 C3 N2 118.92(18) . . ? 
C2 C3 N2 118.84(17) . . ? 
C3 C4 C5 120.2(2) . . ? 
C3 C4 H4A 119.9 . . ? 
C5 C4 H4A 119.9 . . ? 
C6 C5 C4 119.9(2) . . ? 
C6 C5 H5A 120.0 . . ? 
C4 C5 H5A 120.0 . . ? 
C5 C6 C7 121.06(19) . . ? 
C5 C6 H6A 119.5 . . ? 
C7 C6 H6A 119.5 . . ? 
C6 C7 C8 120.60(18) . . ? 
C6 C7 C2 120.17(19) . . ? 
C8 C7 C2 119.22(18) . . ? 
C9 C8 C7 121.19(18) . . ? 
C9 C8 H8A 119.4 . . ? 
C7 C8 H8A 119.4 . . ? 
C8 C9 C10 120.82(19) . . ? 
C8 C9 H9A 119.6 . . ? 
C10 C9 H9A 119.6 . . ? 
C1 C10 C9 120.00(18) . . ? 
C1 C10 C11 124.58(17) . . ? 
C9 C10 C11 115.37(17) . . ? 
N3 C11 C12 120.18(19) . . ? 
N3 C11 C10 122.46(19) . . ? 
C12 C11 C10 117.16(16) . . ? 
C13 C12 C17 118.60(18) . . ? 
C13 C12 C11 120.05(17) . . ? 
C17 C12 C11 121.35(18) . . ? 
C14 C13 C12 121.39(18) . . ? 
C14 C13 H13A 119.3 . . ? 
C12 C13 H13A 119.3 . . ? 
C13 C14 C15 119.25(19) . . ? 
C13 C14 H14A 120.4 . . ? 
C15 C14 H14A 120.4 . . ? 
O1 C15 C16 115.86(18) . . ? 
O1 C15 C14 124.14(19) . . ? 
C16 C15 C14 120.00(19) . . ? 
C17 C16 C15 120.40(19) . . ? 
C17 C16 H16A 119.8 . . ? 
C15 C16 H16A 119.8 . . ? 
C16 C17 C12 120.36(19) . . ? 
C16 C17 H17A 119.8 . . ? 
C12 C17 H17A 119.8 . . ? 
N1 C18 H18A 109.5 . . ? 
N1 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
N1 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
N1 C19 H19A 109.5 . . ? 
N1 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
N1 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
N2 C20 H20A 109.5 . . ? 
N2 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
N2 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
N2 C21 H21A 109.5 . . ? 
N2 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
N2 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
O1 C22 H22A 109.5 . . ? 
O1 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
O1 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
O2S' Cl1 O4S' 106.5(7) . . ? 
O2S' Cl1 O4S 136.2(5) . . ? 
O4S' Cl1 O4S 37.2(6) . . ? 
O2S' Cl1 O3S' 108.6(10) . . ? 
O4S' Cl1 O3S' 115.6(9) . . ? 
O4S Cl1 O3S' 82.2(7) . . ? 
O2S' Cl1 O2S 27.7(4) . . ? 
O4S' Cl1 O2S 80.8(6) . . ? 
O4S Cl1 O2S 108.6(3) . . ? 
O3S' Cl1 O2S 112.3(9) . . ? 
O2S' Cl1 O3S 94.3(5) . . ? 
O4S' Cl1 O3S 141.4(7) . . ? 
O4S Cl1 O3S 107.1(3) . . ? 
O3S' Cl1 O3S 25.8(7) . . ? 
O2S Cl1 O3S 109.3(2) . . ? 
O2S' Cl1 O1S 98.4(5) . . ? 
O4S' Cl1 O1S 99.5(7) . . ? 
O4S Cl1 O1S 109.25(16) . . ? 
O3S' Cl1 O1S 125.8(9) . . ? 
O2S Cl1 O1S 113.12(18) . . ? 
O3S Cl1 O1S 109.3(2) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C19 N1 C1 C10 58.0(2) . . . . ? 
C18 N1 C1 C10 -73.6(2) . . . . ? 
C19 N1 C1 C2 -123.87(18) . . . . ? 
C18 N1 C1 C2 104.46(19) . . . . ? 
C10 C1 C2 C3 -176.02(18) . . . . ? 
N1 C1 C2 C3 5.8(3) . . . . ? 
C10 C1 C2 C7 3.6(3) . . . . ? 
N1 C1 C2 C7 -174.55(16) . . . . ? 
C7 C2 C3 C4 1.2(3) . . . . ? 
C1 C2 C3 C4 -179.18(19) . . . . ? 
C7 C2 C3 N2 -177.53(16) . . . . ? 
C1 C2 C3 N2 2.1(3) . . . . ? 
C21 N2 C3 C4 -68.8(2) . . . . ? 
C20 N2 C3 C4 58.2(2) . . . . ? 
C21 N2 C3 C2 110.0(2) . . . . ? 
C20 N2 C3 C2 -123.0(2) . . . . ? 
C2 C3 C4 C5 -0.1(3) . . . . ? 
N2 C3 C4 C5 178.64(19) . . . . ? 
C3 C4 C5 C6 -0.9(3) . . . . ? 
C4 C5 C6 C7 0.7(3) . . . . ? 
C5 C6 C7 C8 -178.0(2) . . . . ? 
C5 C6 C7 C2 0.5(3) . . . . ? 
C3 C2 C7 C6 -1.4(3) . . . . ? 
C1 C2 C7 C6 178.98(17) . . . . ? 
C3 C2 C7 C8 177.13(17) . . . . ? 
C1 C2 C7 C8 -2.5(3) . . . . ? 
C6 C7 C8 C9 178.14(19) . . . . ? 
C2 C7 C8 C9 -0.4(3) . . . . ? 
C7 C8 C9 C10 2.3(3) . . . . ? 
C2 C1 C10 C9 -1.8(3) . . . . ? 
N1 C1 C10 C9 176.21(17) . . . . ? 
C2 C1 C10 C11 -179.39(17) . . . . ? 
N1 C1 C10 C11 -1.4(3) . . . . ? 
C8 C9 C10 C1 -1.2(3) . . . . ? 
C8 C9 C10 C11 176.64(18) . . . . ? 
C1 C10 C11 N3 82.2(3) . . . . ? 
C9 C10 C11 N3 -95.5(2) . . . . ? 
C1 C10 C11 C12 -103.0(2) . . . . ? 
C9 C10 C11 C12 79.3(2) . . . . ? 
N3 C11 C12 C13 3.6(3) . . . . ? 
C10 C11 C12 C13 -171.32(17) . . . . ? 
N3 C11 C12 C17 -176.6(2) . . . . ? 
C10 C11 C12 C17 8.4(3) . . . . ? 
C17 C12 C13 C14 -0.1(3) . . . . ? 
C11 C12 C13 C14 179.68(18) . . . . ? 
C12 C13 C14 C15 0.2(3) . . . . ? 
C22 O1 C15 C16 178.1(2) . . . . ? 
C22 O1 C15 C14 -1.9(3) . . . . ? 
C13 C14 C15 O1 179.89(19) . . . . ? 
C13 C14 C15 C16 -0.1(3) . . . . ? 
O1 C15 C16 C17 179.9(2) . . . . ? 
C14 C15 C16 C17 -0.2(3) . . . . ? 
C15 C16 C17 C12 0.3(3) . . . . ? 
C13 C12 C17 C16 -0.2(3) . . . . ? 
C11 C12 C17 C16 -179.9(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              29.34 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.545 
_refine_diff_density_min   -0.388 
_refine_diff_density_rms    0.064 

_publ_section_references 
; 
Bruker (2009). APEX2, SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;

_publ_section_exptl_refinement
;
The H2 and H3 hydrogen atoms attached to the N2 and N3 atoms, correspondingly
were found in the difference Fourier synthesis. The H3 atom was refined 
isotropically without any constraints. The H2 atom was normalized
on 0.9 Ang. and refined in isotropic approximatiom within riding model
with the Uiso(H) parameters equal to 1.2 Ueq(N). The H(C) atom positions
were calculated. All the hydrogen atoms were refined in isotropic 
approximatiom within riding model with the Uiso(H) parameters equal to
1.5 Ueq(Ci), 1.2 Ueq(Cj), where U(Ci) and U(Cj) are 
the equivalent thermal parameters of the methyl carbons and all the 
other carbons, to which corresponding H atoms are bonded
The O2S, O3S, O4S atoms of the anion are disordered over two positions
with occupancies equal to 0.847(12):0.153(12). Major part was refined 
in anisotropic approximation while the minor part was refined isotropically
;

