data_x85552
_audit_creation_date              2016-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_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.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C24 H15 N O2'
_chemical_formula_sum             'C24 H15 N O2'
_chemical_formula_weight          349.37
_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' 0.0033 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            15
_space_group_name_H-M_alt         'C 1 2/c 1'
_space_group_name_Hall            '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                    9.4955(3)
_cell_length_b                    25.1250(9)
_cell_length_c                    22.1462(8)
_cell_angle_alpha                 90
_cell_angle_beta                  101.7566(17)
_cell_angle_gamma                 90
_cell_volume                      5172.7(3)
_cell_formula_units_Z             12
_cell_measurement_reflns_used     9906
_cell_measurement_temperature     100
_cell_measurement_theta_max       27.656
_cell_measurement_theta_min       2.336
_shelx_estimated_absorpt_T_max    0.993
_shelx_estimated_absorpt_T_min    0.971
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_correction_T_min   0.6950
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.9321.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             red
_exptl_crystal_colour_primary     red
_exptl_crystal_density_diffrn     1.346
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'PLATE'
_exptl_crystal_F_000              2184
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.32
_exptl_crystal_size_min           0.08
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0418
_diffrn_reflns_av_unetI/netI      0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        33
_diffrn_reflns_limit_k_min        -33
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_number             45962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full         26.000
_diffrn_reflns_theta_max          28.003
_diffrn_reflns_theta_min          2.336
_diffrn_ambient_temperature       100
_diffrn_detector_area_resol_mean  8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'sealed tube'
_diffrn_special_details           ?
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 4584
_reflns_number_total              6250
_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        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'XL (Sheldrick, 2008)'
_computing_structure_solution     'XS (Sheldrick, 2008)'
_refine_diff_density_max          0.317
_refine_diff_density_min          -0.279
_refine_diff_density_rms          0.043
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      397
_refine_ls_number_reflns          6250
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0691
_refine_ls_R_factor_gt            0.0448
_refine_ls_restrained_S_all       1.025
_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)+(0.0536P)²+3.4891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1073
_refine_ls_wR_factor_ref          0.1196
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O14B) = Uanis(O13A)
3. Others
 Fixed Sof: C12A(0.5) C13A(0.5) O13A(0.5) C14A(0.5) H14A(0.5) C15A(0.5)
 H15A(0.5) C13B(0.5) H13B(0.5) O14B(0.5) C14B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C3A(H3A),
  C4A(H4A), C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A), C14A(H14A), C15A(H15A),
 C13B(H13B)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_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
 N1 N 1.09274(12) 0.11873(5) 0.59016(6) 0.0231(3) Uani 1 1 d . . . . .
 C2 C 1.17512(15) 0.07178(6) 0.59712(7) 0.0264(3) Uani 1 1 d . . . . .
 C3 C 1.13552(17) 0.02000(6) 0.57849(8) 0.0325(4) Uani 1 1 d . . . . .
 H3 H 1.0400 0.0118 0.5581 0.039 Uiso 1 1 calc R . . . .
 C4 C 1.2405(2) -0.01912(7) 0.59085(9) 0.0445(5) Uani 1 1 d . . . . .
 H4 H 1.2167 -0.0546 0.5777 0.053 Uiso 1 1 calc R . . . .
 C5 C 1.3803(2) -0.00767(8) 0.62212(9) 0.0484(5) Uani 1 1 d . . . . .
 H5 H 1.4488 -0.0356 0.6313 0.058 Uiso 1 1 calc R . . . .
 C6 C 1.41980(17) 0.04352(8) 0.63973(8) 0.0425(5) Uani 1 1 d . . . . .
 H6 H 1.5152 0.0511 0.6608 0.051 Uiso 1 1 calc R . . . .
 C7 C 1.31743(16) 0.08450(7) 0.62621(7) 0.0318(4) Uani 1 1 d . . . . .
 C8 C 1.32203(15) 0.14094(7) 0.63712(7) 0.0311(4) Uani 1 1 d . . . . .
 C9 C 1.42991(17) 0.17584(8) 0.66556(8) 0.0407(4) Uani 1 1 d . . . . .
 H9 H 1.5253 0.1634 0.6801 0.049 Uiso 1 1 calc R . . . .
 C10 C 1.39652(19) 0.22825(9) 0.67231(8) 0.0452(5) Uani 1 1 d . . . . .
 H10 H 1.4699 0.2521 0.6912 0.054 Uiso 1 1 calc R . . . .
 C11 C 1.25624(19) 0.24732(7) 0.65189(8) 0.0390(4) Uani 1 1 d . . . . .
 H11 H 1.2357 0.2837 0.6582 0.047 Uiso 1 1 calc R . . . .
 C12 C 1.14682(17) 0.21405(6) 0.62258(7) 0.0296(3) Uani 1 1 d . . . . .
 H12 H 1.0518 0.2270 0.6083 0.036 Uiso 1 1 calc R . . . .
 C13 C 1.18169(15) 0.16097(6) 0.61486(7) 0.0257(3) Uani 1 1 d . . . . .
 C14 C 0.94164(14) 0.12201(5) 0.56797(6) 0.0209(3) Uani 1 1 d . . . . .
 C15 C 0.88248(14) 0.16325(5) 0.52862(7) 0.0221(3) Uani 1 1 d . . . . .
 H15 H 0.9435 0.1891 0.5160 0.027 Uiso 1 1 calc R . . . .
 C16 C 0.73483(14) 0.16642(5) 0.50797(7) 0.0217(3) Uani 1 1 d . . . . .
 H16 H 0.6948 0.1955 0.4828 0.026 Uiso 1 1 calc R . . . .
 C17 C 0.64388(14) 0.12723(5) 0.52386(6) 0.0208(3) Uani 1 1 d . . . . .
 C18 C 0.70549(14) 0.08600(5) 0.56279(7) 0.0222(3) Uani 1 1 d . . . . .
 H18 H 0.6454 0.0590 0.5737 0.027 Uiso 1 1 calc R . . . .
 C19 C 0.85213(14) 0.08375(5) 0.58573(7) 0.0220(3) Uani 1 1 d . . . . .
 H19 H 0.8916 0.0562 0.6135 0.026 Uiso 1 1 calc R . . . .
 C20 C 0.48726(14) 0.12663(5) 0.49845(6) 0.0205(3) Uani 1 1 d . . . . .
 O21 O 0.46024(10) 0.21947(4) 0.51383(5) 0.0280(2) Uani 1 1 d . . . . .
 C21 C 0.40239(14) 0.17700(5) 0.49652(6) 0.0210(3) Uani 1 1 d . . . . .
 C22 C 0.24491(14) 0.17444(6) 0.47321(7) 0.0245(3) Uani 1 1 d . . . . .
 H22 H 0.1893 0.2060 0.4724 0.029 Uiso 1 1 calc R . . . .
 C23 C 0.17917(15) 0.12890(6) 0.45332(7) 0.0256(3) Uani 1 1 d . . . . .
 H23 H 0.0778 0.1285 0.4390 0.031 Uiso 1 1 calc R . . . .
 C24 C 0.26140(15) 0.07941(6) 0.45330(7) 0.0253(3) Uani 1 1 d . . . . .
 O24 O 0.20252(12) 0.03806(4) 0.43276(6) 0.0382(3) Uani 1 1 d . . . . .
 C25 C 0.41744(15) 0.08147(6) 0.47791(7) 0.0244(3) Uani 1 1 d . . . . .
 H25 H 0.4713 0.0495 0.4794 0.029 Uiso 1 1 calc R . . . .
 N1A N 0.0000 0.21706(7) 0.7500 0.0250(4) Uani 1 2 d S T P . .
 C2A C -0.09861(15) 0.24977(6) 0.71119(7) 0.0258(3) Uani 1 1 d . . . . .
 C3A C -0.21187(15) 0.23556(7) 0.66339(7) 0.0287(3) Uani 1 1 d . . . . .
 H3A H -0.2334 0.1993 0.6532 0.034 Uiso 1 1 calc R . . . .
 C4A C -0.29167(16) 0.27640(7) 0.63135(7) 0.0328(4) Uani 1 1 d . . . . .
 H4A H -0.3701 0.2679 0.5988 0.039 Uiso 1 1 calc R . . . .
 C5A C -0.26006(17) 0.32977(7) 0.64559(8) 0.0365(4) Uani 1 1 d . . . . .
 H5A H -0.3185 0.3568 0.6233 0.044 Uiso 1 1 calc R . . . .
 C6A C -0.14487(17) 0.34373(7) 0.69175(8) 0.0328(4) Uani 1 1 d . . . . .
 H6A H -0.1219 0.3801 0.7006 0.039 Uiso 1 1 calc R . . . .
 C7A C -0.06287(15) 0.30332(6) 0.72518(7) 0.0270(3) Uani 1 1 d . . . . .
 C8A C 0.0000 0.16055(8) 0.7500 0.0255(4) Uani 1 2 d S T P . .
 C9A C 0.12618(16) 0.13279(6) 0.74832(7) 0.0287(3) Uani 1 1 d . . . . .
 H9A H 0.2124 0.1517 0.7473 0.034 Uiso 1 1 calc R . . . .
 C10A C 0.12581(18) 0.07787(6) 0.74817(7) 0.0329(4) Uani 1 1 d . . . . .
 H10A H 0.2120 0.0592 0.7468 0.039 Uiso 1 1 calc R . . . .
 C11A C 0.0000 0.04933(9) 0.7500 0.0343(5) Uani 1 2 d S T P A .
 C12A C -0.0229(11) -0.00976(13) 0.7446(7) 0.033(2) Uani 0.5 1 d . . . . .
 C13A C -0.1125(8) -0.0402(4) 0.7226(5) 0.0458(18) Uani 0.5 1 d . . . A -1
 O13A O -0.2169(7) -0.0229(2) 0.6956(2) 0.0796(9) Uani 0.5 1 d . . . A -1
 C14A C -0.0807(7) -0.1018(2) 0.7264(3) 0.0515(14) Uani 0.5 1 d . . . A -1
 H14A H -0.1532 -0.1248 0.7047 0.062 Uiso 0.5 1 calc R . . A -1
 C15A C -0.0393(7) -0.12454(19) 0.7424(4) 0.056(2) Uani 0.5 1 d . . . . .
 H15A H -0.0740 -0.1597 0.7453 0.067 Uiso 0.5 1 calc R . . B -2
 C13B C -0.149(2) -0.0373(6) 0.7156(6) 0.137(7) Uani 0.5 1 d . . . A -2
 H13B H -0.2310 -0.0167 0.6984 0.165 Uiso 0.5 1 calc R . . A -2
 O14B O -0.2657(5) -0.11204(12) 0.68217(15) 0.0796(9) Uani 0.5 1 d . . . A -2
 C14B C -0.1601(6) -0.0926(2) 0.7104(2) 0.0461(12) Uani 0.5 1 d . . . 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
 N1 C2 1.4065(18) . ?
 N1 C13 1.3967(18) . ?
 N1 C14 1.4211(17) . ?
 C2 C3 1.393(2) . ?
 C2 C7 1.410(2) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.387(2) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.397(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.374(3) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.406(2) . ?
 C7 C8 1.438(2) . ?
 C8 C9 1.397(2) . ?
 C8 C13 1.416(2) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.370(3) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.401(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.387(2) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.393(2) . ?
 C14 C15 1.396(2) . ?
 C14 C19 1.3919(19) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.3855(19) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.4011(19) . ?
 C17 C18 1.3974(19) . ?
 C17 C20 1.4791(18) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.3827(19) . ?
 C19 H19 0.9500 . ?
 C20 C21 1.4962(19) . ?
 C20 C25 1.3458(19) . ?
 O21 C21 1.2254(17) . ?
 C21 C22 1.4806(19) . ?
 C22 H22 0.9500 . ?
 C22 C23 1.334(2) . ?
 C23 H23 0.9500 . ?
 C23 C24 1.468(2) . ?
 C24 O24 1.2228(17) . ?
 C24 C25 1.472(2) . ?
 C25 H25 0.9500 . ?
 N1A C2A 1.4011(17) . ?
 N1A C2A 1.4011(17) 2_556 ?
 N1A C8A 1.420(3) . ?
 C2A C3A 1.393(2) . ?
 C2A C7A 1.407(2) . ?
 C3A H3A 0.9500 . ?
 C3A C4A 1.383(2) . ?
 C4A H4A 0.9500 . ?
 C4A C5A 1.396(2) . ?
 C5A H5A 0.9500 . ?
 C5A C6A 1.382(2) . ?
 C6A H6A 0.9500 . ?
 C6A C7A 1.397(2) . ?
 C7A C7A 1.449(3) 2_556 ?
 C8A C9A 1.3934(18) 2_556 ?
 C8A C9A 1.3934(18) . ?
 C9A H9A 0.9500 . ?
 C9A C10A 1.380(2) . ?
 C10A H10A 0.9500 . ?
 C10A C11A 1.401(2) . ?
 C11A C10A 1.401(2) 2_556 ?
 C11A C12A 1.502(4) . ?
 C11A C12A 1.502(4) 2_556 ?
 C12A C12A 0.452(17) 2_556 ?
 C12A C13A 1.174(12) . ?
 C12A C13B 1.415(18) . ?
 C13A C12A 1.545(10) 2_556 ?
 C13A O13A 1.135(12) . ?
 C13A C14A 1.576(12) . ?
 C14A H14A 0.9500 . ?
 C14A C15A 1.334(8) 2_556 ?
 C15A C15A 0.754(11) 2_556 ?
 C15A H15A 0.9500 . ?
 C15A C14B 1.459(6) . ?
 C13B H13B 0.9500 . ?
 C13B C14B 1.398(16) . ?
 O14B C14B 1.175(6) . ?

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
 C2 N1 C14 125.90(12) . . ?
 C13 N1 C2 108.42(12) . . ?
 C13 N1 C14 125.36(12) . . ?
 N1 C2 C7 108.65(13) . . ?
 C3 C2 N1 129.81(14) . . ?
 C3 C2 C7 121.52(14) . . ?
 C2 C3 H3 121.2 . . ?
 C4 C3 C2 117.62(16) . . ?
 C4 C3 H3 121.2 . . ?
 C3 C4 H4 119.2 . . ?
 C3 C4 C5 121.62(18) . . ?
 C5 C4 H4 119.2 . . ?
 C4 C5 H5 119.7 . . ?
 C6 C5 C4 120.69(16) . . ?
 C6 C5 H5 119.7 . . ?
 C5 C6 H6 120.4 . . ?
 C5 C6 C7 119.23(17) . . ?
 C7 C6 H6 120.4 . . ?
 C2 C7 C8 107.09(13) . . ?
 C6 C7 C2 119.21(17) . . ?
 C6 C7 C8 133.68(16) . . ?
 C9 C8 C7 133.57(16) . . ?
 C9 C8 C13 119.04(16) . . ?
 C13 C8 C7 107.33(13) . . ?
 C8 C9 H9 120.4 . . ?
 C10 C9 C8 119.20(16) . . ?
 C10 C9 H9 120.4 . . ?
 C9 C10 H10 119.3 . . ?
 C9 C10 C11 121.30(16) . . ?
 C11 C10 H10 119.3 . . ?
 C10 C11 H11 119.4 . . ?
 C12 C11 C10 121.14(17) . . ?
 C12 C11 H11 119.4 . . ?
 C11 C12 H12 121.3 . . ?
 C11 C12 C13 117.40(15) . . ?
 C13 C12 H12 121.3 . . ?
 N1 C13 C8 108.50(13) . . ?
 C12 C13 N1 129.47(13) . . ?
 C12 C13 C8 121.87(14) . . ?
 C15 C14 N1 120.56(12) . . ?
 C19 C14 N1 119.59(12) . . ?
 C19 C14 C15 119.85(12) . . ?
 C14 C15 H15 120.0 . . ?
 C16 C15 C14 120.01(13) . . ?
 C16 C15 H15 120.0 . . ?
 C15 C16 H16 119.6 . . ?
 C15 C16 C17 120.71(13) . . ?
 C17 C16 H16 119.6 . . ?
 C16 C17 C20 122.34(12) . . ?
 C18 C17 C16 118.29(12) . . ?
 C18 C17 C20 119.30(12) . . ?
 C17 C18 H18 119.3 . . ?
 C19 C18 C17 121.38(13) . . ?
 C19 C18 H18 119.3 . . ?
 C14 C19 H19 120.2 . . ?
 C18 C19 C14 119.67(13) . . ?
 C18 C19 H19 120.2 . . ?
 C17 C20 C21 119.75(12) . . ?
 C25 C20 C17 121.67(12) . . ?
 C25 C20 C21 118.57(12) . . ?
 O21 C21 C20 121.54(12) . . ?
 O21 C21 C22 120.23(12) . . ?
 C22 C21 C20 118.23(12) . . ?
 C21 C22 H22 119.2 . . ?
 C23 C22 C21 121.57(13) . . ?
 C23 C22 H22 119.2 . . ?
 C22 C23 H23 119.6 . . ?
 C22 C23 C24 120.88(13) . . ?
 C24 C23 H23 119.6 . . ?
 C23 C24 C25 117.74(12) . . ?
 O24 C24 C23 121.11(13) . . ?
 O24 C24 C25 121.14(13) . . ?
 C20 C25 C24 122.97(13) . . ?
 C20 C25 H25 118.5 . . ?
 C24 C25 H25 118.5 . . ?
 C2A N1A C2A 108.17(17) . 2_556 ?
 C2A N1A C8A 125.92(8) . . ?
 C2A N1A C8A 125.92(8) 2_556 . ?
 N1A C2A C7A 108.96(13) . . ?
 C3A C2A N1A 129.18(14) . . ?
 C3A C2A C7A 121.79(14) . . ?
 C2A C3A H3A 121.4 . . ?
 C4A C3A C2A 117.21(15) . . ?
 C4A C3A H3A 121.4 . . ?
 C3A C4A H4A 119.1 . . ?
 C3A C4A C5A 121.78(15) . . ?
 C5A C4A H4A 119.1 . . ?
 C4A C5A H5A 119.6 . . ?
 C6A C5A C4A 120.83(15) . . ?
 C6A C5A H5A 119.6 . . ?
 C5A C6A H6A 120.7 . . ?
 C5A C6A C7A 118.65(15) . . ?
 C7A C6A H6A 120.7 . . ?
 C2A C7A C7A 106.96(8) . 2_556 ?
 C6A C7A C2A 119.68(14) . . ?
 C6A C7A C7A 133.35(9) . 2_556 ?
 C9A C8A N1A 120.03(10) 2_556 . ?
 C9A C8A N1A 120.03(10) . . ?
 C9A C8A C9A 119.9(2) . 2_556 ?
 C8A C9A H9A 120.0 . . ?
 C10A C9A C8A 119.92(15) . . ?
 C10A C9A H9A 120.0 . . ?
 C9A C10A H10A 119.5 . . ?
 C9A C10A C11A 120.90(16) . . ?
 C11A C10A H10A 119.5 . . ?
 C10A C11A C10A 118.4(2) . 2_556 ?
 C10A C11A C12A 127.9(5) . . ?
 C10A C11A C12A 113.4(5) . 2_556 ?
 C10A C11A C12A 127.9(5) 2_556 2_556 ?
 C10A C11A C12A 113.5(5) 2_556 . ?
 C12A C11A C12A 17.3(7) . 2_556 ?
 C12A C12A C11A 81.3(3) 2_556 . ?
 C12A C12A C13A 139.3(7) 2_556 . ?
 C12A C12A C13B 150.8(7) 2_556 . ?
 C13A C12A C11A 139.4(9) . . ?
 C13B C12A C11A 127.9(9) . . ?
 C12A C13A C12A 11.0(5) . 2_556 ?
 C12A C13A C14A 120.2(9) . . ?
 C12A C13A C14A 109.2(7) 2_556 . ?
 O13A C13A C12A 116.7(10) . . ?
 O13A C13A C12A 127.7(9) . 2_556 ?
 O13A C13A C14A 122.8(7) . . ?
 C13A C14A H14A 117.2 . . ?
 C15A C14A C13A 125.6(6) 2_556 . ?
 C15A C14A H14A 117.2 2_556 . ?
 C15A C15A H15A 107.2 2_556 . ?
 C15A C15A C14B 145.6(5) 2_556 . ?
 C14B C15A H15A 107.2 . . ?
 C12A C13B H13B 117.7 . . ?
 C14B C13B C12A 124.6(14) . . ?
 C14B C13B H13B 117.7 . . ?
 C13B C14B C15A 117.8(9) . . ?
 O14B C14B C15A 122.1(5) . . ?
 O14B C14B C13B 120.0(9) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
 C3 H3 O24 0.95 2.67 3.488(2) 145.2 5_656
 C22 H22 O21 0.95 2.41 3.3480(17) 170.5 7_556
 C4A H4A O21 0.95 2.53 3.4453(19) 163.0 1_455

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
 N1 C2 C3 C4 179.24(15) . . . . ?
 N1 C2 C7 C6 178.30(14) . . . . ?
 N1 C2 C7 C8 -0.19(16) . . . . ?
 N1 C14 C15 C16 -179.12(13) . . . . ?
 N1 C14 C19 C18 -178.16(13) . . . . ?
 C2 N1 C13 C8 0.61(16) . . . . ?
 C2 N1 C13 C12 -174.86(15) . . . . ?
 C2 N1 C14 C15 -140.32(14) . . . . ?
 C2 N1 C14 C19 39.7(2) . . . . ?
 C2 C3 C4 C5 1.5(3) . . . . ?
 C2 C7 C8 C9 177.71(17) . . . . ?
 C2 C7 C8 C13 0.56(17) . . . . ?
 C3 C2 C7 C6 -3.5(2) . . . . ?
 C3 C2 C7 C8 178.00(14) . . . . ?
 C3 C4 C5 C6 -2.4(3) . . . . ?
 C4 C5 C6 C7 0.3(3) . . . . ?
 C5 C6 C7 C2 2.5(2) . . . . ?
 C5 C6 C7 C8 -179.45(17) . . . . ?
 C6 C7 C8 C9 -0.5(3) . . . . ?
 C6 C7 C8 C13 -177.62(17) . . . . ?
 C7 C2 C3 C4 1.5(2) . . . . ?
 C7 C8 C9 C10 -175.56(17) . . . . ?
 C7 C8 C13 N1 -0.73(16) . . . . ?
 C7 C8 C13 C12 175.16(14) . . . . ?
 C8 C9 C10 C11 0.7(3) . . . . ?
 C9 C8 C13 N1 -178.37(14) . . . . ?
 C9 C8 C13 C12 -2.5(2) . . . . ?
 C9 C10 C11 C12 -1.7(3) . . . . ?
 C10 C11 C12 C13 0.6(2) . . . . ?
 C11 C12 C13 N1 176.43(15) . . . . ?
 C11 C12 C13 C8 1.5(2) . . . . ?
 C13 N1 C2 C3 -178.25(15) . . . . ?
 C13 N1 C2 C7 -0.25(16) . . . . ?
 C13 N1 C14 C15 46.9(2) . . . . ?
 C13 N1 C14 C19 -133.01(15) . . . . ?
 C13 C8 C9 C10 1.3(2) . . . . ?
 C14 N1 C2 C3 8.0(2) . . . . ?
 C14 N1 C2 C7 -174.01(13) . . . . ?
 C14 N1 C13 C8 174.41(13) . . . . ?
 C14 N1 C13 C12 -1.1(2) . . . . ?
 C14 C15 C16 C17 -2.9(2) . . . . ?
 C15 C14 C19 C18 1.9(2) . . . . ?
 C15 C16 C17 C18 2.2(2) . . . . ?
 C15 C16 C17 C20 -174.58(13) . . . . ?
 C16 C17 C18 C19 0.5(2) . . . . ?
 C16 C17 C20 C21 -45.8(2) . . . . ?
 C16 C17 C20 C25 135.54(15) . . . . ?
 C17 C18 C19 C14 -2.6(2) . . . . ?
 C17 C20 C21 O21 2.3(2) . . . . ?
 C17 C20 C21 C22 -177.46(12) . . . . ?
 C17 C20 C25 C24 178.99(13) . . . . ?
 C18 C17 C20 C21 137.36(14) . . . . ?
 C18 C17 C20 C25 -41.3(2) . . . . ?
 C19 C14 C15 C16 0.8(2) . . . . ?
 C20 C17 C18 C19 177.45(13) . . . . ?
 C20 C21 C22 C23 -1.1(2) . . . . ?
 O21 C21 C22 C23 179.14(14) . . . . ?
 C21 C20 C25 C24 0.4(2) . . . . ?
 C21 C22 C23 C24 -0.6(2) . . . . ?
 C22 C23 C24 O24 -176.94(15) . . . . ?
 C22 C23 C24 C25 2.1(2) . . . . ?
 C23 C24 C25 C20 -2.0(2) . . . . ?
 O24 C24 C25 C20 177.03(15) . . . . ?
 C25 C20 C21 O21 -179.05(14) . . . . ?
 C25 C20 C21 C22 1.2(2) . . . . ?
 N1A C2A C3A C4A -178.76(13) . . . . ?
 N1A C2A C7A C6A 179.04(12) . . . . ?
 N1A C2A C7A C7A -0.14(19) . . . 2_556 ?
 N1A C8A C9A C10A -179.84(10) . . . . ?
 C2A N1A C2A C3A 176.95(18) 2_556 . . . ?
 C2A N1A C2A C7A 0.06(8) 2_556 . . . ?
 C2A N1A C8A C9A 130.40(10) 2_556 . . 2_556 ?
 C2A N1A C8A C9A 130.39(10) . . . . ?
 C2A N1A C8A C9A -49.60(10) . . . 2_556 ?
 C2A N1A C8A C9A -49.61(10) 2_556 . . . ?
 C2A C3A C4A C5A 0.6(2) . . . . ?
 C3A C2A C7A C6A 1.9(2) . . . . ?
 C3A C2A C7A C7A -177.31(15) . . . 2_556 ?
 C3A C4A C5A C6A 1.4(3) . . . . ?
 C4A C5A C6A C7A -1.8(2) . . . . ?
 C5A C6A C7A C2A 0.2(2) . . . . ?
 C5A C6A C7A C7A 179.1(2) . . . 2_556 ?
 C7A C2A C3A C4A -2.2(2) . . . . ?
 C8A N1A C2A C3A -3.05(18) . . . . ?
 C8A N1A C2A C7A -179.94(8) . . . . ?
 C8A C9A C10A C11A -0.3(2) . . . . ?
 C9A C8A C9A C10A 0.15(10) 2_556 . . . ?
 C9A C10A C11A C10A 0.16(11) . . . 2_556 ?
 C9A C10A C11A C12A 174.2(7) . . . . ?
 C9A C10A C11A C12A -174.7(7) . . . 2_556 ?
 C10A C11A C12A C12A 37(5) . . . 2_556 ?
 C10A C11A C12A C12A -149(4) 2_556 . . 2_556 ?
 C10A C11A C12A C13A -142.2(19) . . . . ?
 C10A C11A C12A C13A 32(3) 2_556 . . . ?
 C10A C11A C12A C13B 30.0(18) 2_556 . . . ?
 C10A C11A C12A C13B -144.2(12) . . . . ?
 C11A C12A C13A C12A 178(100) . . . 2_556 ?
 C11A C12A C13A O13A 1(3) . . . . ?
 C11A C12A C13A C14A 176.3(16) . . . . ?
 C11A C12A C13B C14B 177.5(12) . . . . ?
 C12A C11A C12A C13A -179(100) 2_556 . . . ?
 C12A C11A C12A C13B 179(100) 2_556 . . . ?
 C12A C12A C13A O13A -177(8) 2_556 . . . ?
 C12A C12A C13A C14A -2(9) 2_556 . . . ?
 C12A C12A C13B C14B -4(11) 2_556 . . . ?
 C12A C13A C14A C15A 5.7(15) . . . 2_556 ?
 C12A C13A C14A C15A 5.4(12) 2_556 . . 2_556 ?
 C12A C13B C14B C15A 6.5(17) . . . . ?
 C12A C13B C14B O14B -175.1(11) . . . . ?
 O13A C13A C14A C15A -179.7(8) . . . 2_556 ?
 C15A C15A C14B C13B -18(3) 2_556 . . . ?
 C15A C15A C14B O14B 164(3) 2_556 . . . ?

_shelx_SHELXL_version_number      '2014/7'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
