data_cu_rs297cu_0m
_audit_creation_date              2017-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number      '2017/1'
_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. (2015a). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2015b). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C22 H24 N2 O2'
_chemical_formula_sum             'C22 H24 N2 O2'
_chemical_formula_weight          348.43
_chemical_absolute_configuration  rmad
_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'
 '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       'orthorhombic'
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'

_cell_length_a                    10.4511(7)
_cell_length_b                    12.4377(8)
_cell_length_c                    14.3024(9)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1859.1(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     2853
_cell_measurement_temperature     296.15
_cell_measurement_theta_max       64.98
_cell_measurement_theta_min       4.71
_shelx_estimated_absorpt_T_max    0.951
_shelx_estimated_absorpt_T_min    0.823
_exptl_absorpt_coefficient_mu     0.634
_exptl_absorpt_correction_T_max   0.7528
_exptl_absorpt_correction_T_min   0.5490
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0624 before and 0.0381 after correction. The Ratio 
of minimum to maximum transmission is 0.7293. The \l/2 correction 
factor is Not present.'
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.245
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        irregular
_exptl_crystal_F_000              744
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.23
_exptl_crystal_size_min           0.08
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0271
_diffrn_reflns_av_unetI/netI      0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_number             6273
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full         66.649
_diffrn_reflns_theta_max          66.649
_diffrn_reflns_theta_min          4.711
_diffrn_ambient_temperature       296.15
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54178
_diffrn_source                    ?
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.696
_reflns_Friedel_fraction_full     0.918
_reflns_Friedel_fraction_max      0.918
_reflns_number_gt                 2870
_reflns_number_total              3130
_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 V8.38A (?, 2016)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution     'XT (Sheldrick, 2015a)'
_refine_diff_density_max          0.098
_refine_diff_density_min          -0.105
_refine_diff_density_rms          0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.19(15)
_refine_ls_extinction_coef        0.0041(6)
_refine_ls_extinction_expression  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method      'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref    1.053
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      256
_refine_ls_number_reflns          3130
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0361
_refine_ls_R_factor_gt            0.0324
_refine_ls_restrained_S_all       1.053
_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)+(0.0473P)²+0.0878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0825
_refine_ls_wR_factor_ref          0.0859
_refine_special_details
;
The pyrrolidine group was highly disordered ; we modeled this disorder
 considering two positions with following occupancies : 0.65 (2) 
 and 0.35(2).
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H11C)=Sof(H11D)=Sof(H14C)=Sof(H14D)=Sof(C12B)=Sof(H12C)=Sof(H12D)=
 Sof(C13B)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12A)=
 Sof(H12B)=Sof(H14A)=Sof(H14B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C9(H9A,H9B), C11(H11A,H11B), C11(H11C,H11D), C12A(H12A,H12B),
  C14(H14A,H14B), C14(H14C,H14D), C12B(H12C,H12D), C13B(H13C,H13D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C22(H22), C21(H21), C20(H20), C19(H19),
 C18(H18)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      ?
_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
 C13A C 1.2129(6) 0.2611(4) 0.9817(5) 0.0699(18) Uani 0.655(13) 1 d . . P A 1
 H13A H 1.174782 0.273265 1.042575 0.084 Uiso 0.655(13) 1 calc R . P A 1
 H13B H 1.287453 0.215370 0.988693 0.084 Uiso 0.655(13) 1 calc R . P A 1
 C1 C 0.5346(2) 0.5831(2) 0.6569(2) 0.0752(7) Uani 1 1 d . . . . .
 H1 H 0.519743 0.617638 0.600264 0.090 Uiso 1 1 calc R . . . .
 C2 C 0.4634(3) 0.6072(3) 0.7353(3) 0.0913(10) Uani 1 1 d . . . . .
 H2 H 0.398671 0.658339 0.731359 0.110 Uiso 1 1 calc R . . . .
 C3 C 0.4866(2) 0.5566(3) 0.8198(2) 0.0836(9) Uani 1 1 d . . . . .
 H3 H 0.437483 0.574448 0.871766 0.100 Uiso 1 1 calc R . . . .
 C4 C 0.5810(2) 0.4804(2) 0.82804(18) 0.0646(6) Uani 1 1 d . . . . .
 H4 H 0.597335 0.446874 0.884910 0.078 Uiso 1 1 calc R . . . .
 C5 C 0.65117(18) 0.45524(17) 0.74893(15) 0.0487(5) Uani 1 1 d . . . . .
 C6 C 0.62837(17) 0.50614(17) 0.66525(15) 0.0516(5) Uani 1 1 d . . . . .
 C7 C 0.7159(2) 0.46314(16) 0.59405(14) 0.0487(5) Uani 1 1 d . . . . .
 C8 C 0.75865(19) 0.37605(15) 0.73768(13) 0.0451(4) Uani 1 1 d . . . . .
 H8 H 0.725288 0.303164 0.746810 0.054 Uiso 1 1 calc R . . . .
 C15 C 0.8750(2) 0.31678(17) 0.58488(14) 0.0518(5) Uani 1 1 d . . . . .
 H15 H 0.871112 0.341190 0.519788 0.062 Uiso 1 1 calc R . . . .
 C16 C 0.8193(3) 0.20341(19) 0.58560(19) 0.0713(7) Uani 1 1 d . . . . .
 H16A H 0.864838 0.159430 0.541596 0.107 Uiso 1 1 calc GR . . . .
 H16B H 0.730529 0.206197 0.568581 0.107 Uiso 1 1 calc GR . . . .
 H16C H 0.827578 0.173235 0.647089 0.107 Uiso 1 1 calc GR . . . .
 C17 C 1.0143(2) 0.32533(17) 0.61388(13) 0.0503(5) Uani 1 1 d . . . . .
 C22 C 1.0710(2) 0.42603(18) 0.62070(16) 0.0583(6) Uani 1 1 d . . . . .
 H22 H 1.022281 0.486818 0.607806 0.070 Uiso 1 1 calc R . . . .
 C21 C 1.1971(2) 0.4384(2) 0.64599(18) 0.0708(7) Uani 1 1 d . . . . .
 H21 H 1.232548 0.506806 0.650705 0.085 Uiso 1 1 calc R . . . .
 C20 C 1.2706(3) 0.3489(3) 0.66428(19) 0.0801(8) Uani 1 1 d . . . . .
 H20 H 1.356007 0.356528 0.681381 0.096 Uiso 1 1 calc R . . . .
 C19 C 1.2175(3) 0.2488(3) 0.6572(2) 0.0809(8) Uani 1 1 d . . . . .
 H19 H 1.267220 0.188342 0.669315 0.097 Uiso 1 1 calc R . . . .
 C18 C 1.0897(3) 0.2365(2) 0.63193(18) 0.0667(6) Uani 1 1 d . . . . .
 H18 H 1.054840 0.167907 0.627172 0.080 Uiso 1 1 calc R . . . .
 C9 C 0.86776(19) 0.39560(16) 0.80690(13) 0.0457(4) Uani 1 1 d . . . . .
 H9A H 0.928972 0.444575 0.778884 0.055 Uiso 1 1 calc R . . . .
 H9B H 0.833476 0.429986 0.862378 0.055 Uiso 1 1 calc R . . . .
 C10 C 0.9365(2) 0.29374(15) 0.83545(13) 0.0464(4) Uani 1 1 d . . . . .
 C11 C 1.1135(2) 0.40756(19) 0.89929(17) 0.0600(6) Uani 1 1 d . . . . .
 H11A H 1.069669 0.449336 0.946759 0.072 Uiso 0.655(13) 1 calc R . P A 1
 H11B H 1.122988 0.450543 0.843129 0.072 Uiso 0.655(13) 1 calc R . P A 1
 H11C H 1.141879 0.440070 0.841234 0.072 Uiso 0.345(13) 1 calc R . P A 2
 H11D H 1.056223 0.457332 0.930488 0.072 Uiso 0.345(13) 1 calc R . P A 2
 C12A C 1.2468(11) 0.3644(10) 0.9355(8) 0.074(2) Uani 0.655(13) 1 d . . P A 1
 H12A H 1.305656 0.352939 0.884054 0.089 Uiso 0.655(13) 1 calc R . P A 1
 H12B H 1.285029 0.414172 0.979669 0.089 Uiso 0.655(13) 1 calc R . P A 1
 C14 C 1.1186(3) 0.2133(2) 0.9153(2) 0.0779(8) Uani 1 1 d . . . . .
 H14A H 1.161700 0.176009 0.864677 0.093 Uiso 0.655(13) 1 calc R . P A 1
 H14B H 1.062185 0.163331 0.947059 0.093 Uiso 0.655(13) 1 calc R . P A 1
 H14C H 1.120783 0.155116 0.870111 0.093 Uiso 0.345(13) 1 calc R . P A 2
 H14D H 1.084533 0.187198 0.974118 0.093 Uiso 0.345(13) 1 calc R . P A 2
 N1 N 0.79282(16) 0.39039(13) 0.63834(11) 0.0453(4) Uani 1 1 d . . . . .
 N2 N 1.04760(18) 0.30651(14) 0.88029(12) 0.0543(4) Uani 1 1 d . . . . .
 O1 O 0.72134(18) 0.48657(14) 0.51085(11) 0.0702(5) Uani 1 1 d . . . . .
 O2 O 0.89001(17) 0.20411(11) 0.82193(11) 0.0638(4) Uani 1 1 d . . . . .
 C12B C 1.219(2) 0.385(3) 0.957(2) 0.089(6) Uani 0.345(13) 1 d . . P A 2
 H12C H 1.194716 0.387277 1.022030 0.106 Uiso 0.345(13) 1 calc R . P A 2
 H12D H 1.287072 0.436478 0.945984 0.106 Uiso 0.345(13) 1 calc R . P A 2
 C13B C 1.2616(11) 0.2709(10) 0.9284(11) 0.086(4) Uani 0.345(13) 1 d . . P A 2
 H13C H 1.311326 0.236535 0.977298 0.103 Uiso 0.345(13) 1 calc R . P A 2
 H13D H 1.310082 0.270990 0.870605 0.103 Uiso 0.345(13) 1 calc R . 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
 C13A H13A 0.9700 . ?
 C13A H13B 0.9700 . ?
 C13A C12A 1.487(15) . ?
 C13A C14 1.492(5) . ?
 C1 H1 0.9300 . ?
 C1 C2 1.380(4) . ?
 C1 C6 1.374(3) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.384(5) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.373(4) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.384(3) . ?
 C5 C6 1.375(3) . ?
 C5 C8 1.503(3) . ?
 C6 C7 1.470(3) . ?
 C7 N1 1.366(3) . ?
 C7 O1 1.226(3) . ?
 C8 H8 0.9800 . ?
 C8 C9 1.530(3) . ?
 C8 N1 1.476(2) . ?
 C15 H15 0.9800 . ?
 C15 C16 1.525(3) . ?
 C15 C17 1.518(3) . ?
 C15 N1 1.470(3) . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 0.9600 . ?
 C17 C22 1.389(3) . ?
 C17 C18 1.382(3) . ?
 C22 H22 0.9300 . ?
 C22 C21 1.375(4) . ?
 C21 H21 0.9300 . ?
 C21 C20 1.378(4) . ?
 C20 H20 0.9300 . ?
 C20 C19 1.367(4) . ?
 C19 H19 0.9300 . ?
 C19 C18 1.392(4) . ?
 C18 H18 0.9300 . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C9 C10 1.513(3) . ?
 C10 N2 1.336(3) . ?
 C10 O2 1.232(2) . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?
 C11 H11C 0.9700 . ?
 C11 H11D 0.9700 . ?
 C11 C12A 1.580(11) . ?
 C11 N2 1.459(3) . ?
 C11 C12B 1.40(3) . ?
 C12A H12A 0.9700 . ?
 C12A H12B 0.9700 . ?
 C14 H14A 0.9700 . ?
 C14 H14B 0.9700 . ?
 C14 H14C 0.9700 . ?
 C14 H14D 0.9700 . ?
 C14 N2 1.465(3) . ?
 C14 C13B 1.668(12) . ?
 C12B H12C 0.9700 . ?
 C12B H12D 0.9700 . ?
 C12B C13B 1.54(3) . ?
 C13B H13C 0.9700 . ?
 C13B H13D 0.9700 . ?

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
 H13A C13A H13B 109.1 . . ?
 C12A C13A H13A 111.2 . . ?
 C12A C13A H13B 111.2 . . ?
 C12A C13A C14 102.7(5) . . ?
 C14 C13A H13A 111.2 . . ?
 C14 C13A H13B 111.2 . . ?
 C2 C1 H1 121.1 . . ?
 C6 C1 H1 121.1 . . ?
 C6 C1 C2 117.7(3) . . ?
 C1 C2 H2 119.5 . . ?
 C1 C2 C3 121.1(3) . . ?
 C3 C2 H2 119.5 . . ?
 C2 C3 H3 119.5 . . ?
 C4 C3 C2 121.0(3) . . ?
 C4 C3 H3 119.5 . . ?
 C3 C4 H4 121.1 . . ?
 C3 C4 C5 117.8(2) . . ?
 C5 C4 H4 121.1 . . ?
 C4 C5 C8 129.2(2) . . ?
 C6 C5 C4 121.0(2) . . ?
 C6 C5 C8 109.77(18) . . ?
 C1 C6 C5 121.3(2) . . ?
 C1 C6 C7 129.5(2) . . ?
 C5 C6 C7 109.13(18) . . ?
 N1 C7 C6 106.62(17) . . ?
 O1 C7 C6 127.9(2) . . ?
 O1 C7 N1 125.4(2) . . ?
 C5 C8 H8 109.0 . . ?
 C5 C8 C9 112.57(15) . . ?
 C9 C8 H8 109.0 . . ?
 N1 C8 C5 101.81(15) . . ?
 N1 C8 H8 109.0 . . ?
 N1 C8 C9 115.06(16) . . ?
 C16 C15 H15 106.1 . . ?
 C17 C15 H15 106.1 . . ?
 C17 C15 C16 115.4(2) . . ?
 N1 C15 H15 106.1 . . ?
 N1 C15 C16 110.47(19) . . ?
 N1 C15 C17 112.00(16) . . ?
 C15 C16 H16A 109.5 . . ?
 C15 C16 H16B 109.5 . . ?
 C15 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 C22 C17 C15 119.46(19) . . ?
 C18 C17 C15 122.8(2) . . ?
 C18 C17 C22 117.7(2) . . ?
 C17 C22 H22 119.0 . . ?
 C21 C22 C17 121.9(2) . . ?
 C21 C22 H22 119.0 . . ?
 C22 C21 H21 120.2 . . ?
 C22 C21 C20 119.6(3) . . ?
 C20 C21 H21 120.2 . . ?
 C21 C20 H20 120.1 . . ?
 C19 C20 C21 119.7(3) . . ?
 C19 C20 H20 120.1 . . ?
 C20 C19 H19 119.7 . . ?
 C20 C19 C18 120.6(3) . . ?
 C18 C19 H19 119.7 . . ?
 C17 C18 C19 120.5(3) . . ?
 C17 C18 H18 119.7 . . ?
 C19 C18 H18 119.7 . . ?
 C8 C9 H9A 108.9 . . ?
 C8 C9 H9B 108.9 . . ?
 H9A C9 H9B 107.7 . . ?
 C10 C9 C8 113.32(16) . . ?
 C10 C9 H9A 108.9 . . ?
 C10 C9 H9B 108.9 . . ?
 N2 C10 C9 116.29(17) . . ?
 O2 C10 C9 121.88(18) . . ?
 O2 C10 N2 121.75(18) . . ?
 H11A C11 H11B 109.4 . . ?
 H11C C11 H11D 108.4 . . ?
 C12A C11 H11A 111.6 . . ?
 C12A C11 H11B 111.6 . . ?
 N2 C11 H11A 111.6 . . ?
 N2 C11 H11B 111.6 . . ?
 N2 C11 H11C 110.1 . . ?
 N2 C11 H11D 110.1 . . ?
 N2 C11 C12A 100.7(5) . . ?
 C12B C11 H11C 110.1 . . ?
 C12B C11 H11D 110.1 . . ?
 C12B C11 N2 107.9(14) . . ?
 C13A C12A C11 103.2(8) . . ?
 C13A C12A H12A 111.1 . . ?
 C13A C12A H12B 111.1 . . ?
 C11 C12A H12A 111.1 . . ?
 C11 C12A H12B 111.1 . . ?
 H12A C12A H12B 109.1 . . ?
 C13A C14 H14A 111.0 . . ?
 C13A C14 H14B 111.0 . . ?
 H14A C14 H14B 109.0 . . ?
 H14C C14 H14D 109.7 . . ?
 N2 C14 C13A 103.7(2) . . ?
 N2 C14 H14A 111.0 . . ?
 N2 C14 H14B 111.0 . . ?
 N2 C14 H14C 112.0 . . ?
 N2 C14 H14D 112.0 . . ?
 N2 C14 C13B 98.8(4) . . ?
 C13B C14 H14C 112.0 . . ?
 C13B C14 H14D 112.0 . . ?
 C7 N1 C8 112.59(16) . . ?
 C7 N1 C15 121.01(17) . . ?
 C15 N1 C8 124.54(16) . . ?
 C10 N2 C11 127.04(17) . . ?
 C10 N2 C14 120.68(18) . . ?
 C11 N2 C14 112.27(18) . . ?
 C11 C12B H12C 110.7 . . ?
 C11 C12B H12D 110.7 . . ?
 C11 C12B C13B 105(2) . . ?
 H12C C12B H12D 108.8 . . ?
 C13B C12B H12C 110.7 . . ?
 C13B C12B H12D 110.7 . . ?
 C14 C13B H13C 111.9 . . ?
 C14 C13B H13D 111.9 . . ?
 C12B C13B C14 99.5(13) . . ?
 C12B C13B H13C 111.9 . . ?
 C12B C13B H13D 111.9 . . ?
 H13C C13B H13D 109.6 . . ?

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
 C13A C14 N2 C10 -164.8(4) . . . . ?
 C13A C14 N2 C11 16.2(4) . . . . ?
 C1 C2 C3 C4 -0.2(5) . . . . ?
 C1 C6 C7 N1 178.4(2) . . . . ?
 C1 C6 C7 O1 -1.4(4) . . . . ?
 C2 C1 C6 C5 -0.4(4) . . . . ?
 C2 C1 C6 C7 178.6(2) . . . . ?
 C2 C3 C4 C5 -0.7(4) . . . . ?
 C3 C4 C5 C6 1.1(3) . . . . ?
 C3 C4 C5 C8 -180.0(2) . . . . ?
 C4 C5 C6 C1 -0.6(3) . . . . ?
 C4 C5 C6 C7 -179.70(18) . . . . ?
 C4 C5 C8 C9 -54.8(3) . . . . ?
 C4 C5 C8 N1 -178.5(2) . . . . ?
 C5 C6 C7 N1 -2.5(2) . . . . ?
 C5 C6 C7 O1 177.7(2) . . . . ?
 C5 C8 C9 C10 148.54(17) . . . . ?
 C5 C8 N1 C7 -2.2(2) . . . . ?
 C5 C8 N1 C15 -166.70(17) . . . . ?
 C6 C1 C2 C3 0.8(5) . . . . ?
 C6 C5 C8 C9 124.30(18) . . . . ?
 C6 C5 C8 N1 0.5(2) . . . . ?
 C6 C7 N1 C8 2.9(2) . . . . ?
 C6 C7 N1 C15 168.04(17) . . . . ?
 C8 C5 C6 C1 -179.7(2) . . . . ?
 C8 C5 C6 C7 1.1(2) . . . . ?
 C8 C9 C10 N2 167.02(17) . . . . ?
 C8 C9 C10 O2 -16.2(3) . . . . ?
 C15 C17 C22 C21 -179.5(2) . . . . ?
 C15 C17 C18 C19 179.2(2) . . . . ?
 C16 C15 C17 C22 -176.2(2) . . . . ?
 C16 C15 C17 C18 5.5(3) . . . . ?
 C16 C15 N1 C7 -105.2(2) . . . . ?
 C16 C15 N1 C8 58.0(3) . . . . ?
 C17 C15 N1 C7 124.66(19) . . . . ?
 C17 C15 N1 C8 -72.1(2) . . . . ?
 C17 C22 C21 C20 0.7(4) . . . . ?
 C22 C17 C18 C19 0.8(3) . . . . ?
 C22 C21 C20 C19 0.0(4) . . . . ?
 C21 C20 C19 C18 -0.2(4) . . . . ?
 C20 C19 C18 C17 -0.2(4) . . . . ?
 C18 C17 C22 C21 -1.1(3) . . . . ?
 C9 C8 N1 C7 -124.26(18) . . . . ?
 C9 C8 N1 C15 71.2(2) . . . . ?
 C9 C10 N2 C11 -4.3(3) . . . . ?
 C9 C10 N2 C14 176.8(2) . . . . ?
 C11 C12B C13B C14 -40(2) . . . . ?
 C12A C13A C14 N2 -36.0(7) . . . . ?
 C12A C11 N2 C10 -169.7(4) . . . . ?
 C12A C11 N2 C14 9.2(5) . . . . ?
 C14 C13A C12A C11 42.0(8) . . . . ?
 N1 C8 C9 C10 -95.4(2) . . . . ?
 N1 C15 C17 C22 -48.7(3) . . . . ?
 N1 C15 C17 C18 133.0(2) . . . . ?
 N2 C11 C12A C13A -31.4(7) . . . . ?
 N2 C11 C12B C13B 31.3(19) . . . . ?
 N2 C14 C13B C12B 33.6(15) . . . . ?
 O1 C7 N1 C8 -177.2(2) . . . . ?
 O1 C7 N1 C15 -12.1(3) . . . . ?
 O2 C10 N2 C11 178.9(2) . . . . ?
 O2 C10 N2 C14 0.0(3) . . . . ?
 C12B C11 N2 C10 173.6(10) . . . . ?
 C12B C11 N2 C14 -7.4(10) . . . . ?
 C13B C14 N2 C10 161.5(6) . . . . ?
 C13B C14 N2 C11 -17.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
