# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9b
_database_code_depnum_ccdc_archive 'CCDC 1547596'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2016-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H18 N4 O2'
_chemical_formula_sum            'C24 H18 N4 O2'
_chemical_formula_weight         394.42
_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      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                   8.7409(5)
_cell_length_b                   9.6037(6)
_cell_length_c                   12.1665(7)
_cell_angle_alpha                72.299(4)
_cell_angle_beta                 87.366(4)
_cell_angle_gamma                72.955(5)
_cell_volume                     929.19(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.744
_cell_measurement_theta_min      2.329
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0666 before and 0.0485 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0725 before and 0.0532 after correction.
 The Ratio of minimum to maximum transmission is 0.90.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 24553 reflections, Rint = 0.0713
 (7063 with I > 3sig(I), Rint = 0.0393)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.189
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.759
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2861
_reflns_number_total             3785
_reflns_special_details          
;
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.050
_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)+(0.0429P)²+0.4336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6697(14) 0.3303(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3C,H3D), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.6362(2) 0.6675(2) 0.06537(16) 0.0292(5) Uani 1 1 d . . . . .
O2 O 0.5399(2) 0.4861(2) 0.16386(17) 0.0313(5) Uani 1 1 d . . . . .
N1 N 0.5360(3) 0.8038(2) 0.63543(18) 0.0183(5) Uani 1 1 d . . . . .
N2 N 0.5944(3) 0.5935(2) 0.15629(19) 0.0210(5) Uani 1 1 d . . . . .
N3 N 0.3465(3) 0.5981(3) 0.3171(2) 0.0221(5) Uani 1 1 d . . . . .
N4 N 0.2489(3) 0.7065(2) 0.56034(19) 0.0240(5) Uani 1 1 d . . . . .
C1 C 0.6226(3) 0.7362(3) 0.4502(2) 0.0161(5) Uani 1 1 d . . . . .
C2 C 0.7541(3) 0.7210(3) 0.3770(2) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.9042(3) 0.7485(3) 0.4104(2) 0.0240(6) Uani 1 1 d . . . . .
H3C H 0.9694 0.6549 0.4645 0.029 Uiso 1 1 calc R . . . .
H3D H 0.9650 0.7722 0.3420 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8750(3) 0.8745(3) 0.4636(2) 0.0227(6) Uani 1 1 d . . . . .
H4A H 0.9744 0.8706 0.4985 0.027 Uiso 1 1 calc R . . . .
H4B H 0.8369 0.9725 0.4044 0.027 Uiso 1 1 calc R . . . .
C5 C 0.7545(3) 0.8596(3) 0.5528(2) 0.0173(5) Uani 1 1 d . . . . .
C6 C 0.6371(3) 0.7940(3) 0.5445(2) 0.0162(5) Uani 1 1 d . . . . .
C7 C 0.7299(3) 0.9086(3) 0.6532(2) 0.0175(5) Uani 1 1 d . . . . .
C8 C 0.5915(3) 0.8730(3) 0.7026(2) 0.0159(5) Uani 1 1 d . . . . .
C9 C 0.5311(3) 0.9038(3) 0.8041(2) 0.0192(6) Uani 1 1 d . . . . .
C10 C 0.6158(3) 0.9721(3) 0.8541(2) 0.0220(6) Uani 1 1 d . . . . .
H10 H 0.5790 0.9959 0.9210 0.026 Uiso 1 1 calc R . . . .
C11 C 0.7552(3) 1.0067(3) 0.8077(2) 0.0242(6) Uani 1 1 d . . . . .
H11 H 0.8090 1.0511 0.8451 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8137(3) 0.9760(3) 0.7078(2) 0.0224(6) Uani 1 1 d . . . . .
H12 H 0.9059 0.9992 0.6773 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3844(3) 0.8627(3) 0.8551(2) 0.0244(6) Uani 1 1 d . . . . .
H13A H 0.2971 0.9087 0.7982 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.3564 0.8996 0.9206 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.4059 0.7536 0.8792 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.7453(3) 0.6710(3) 0.2816(2) 0.0176(5) Uani 1 1 d . . . . .
C15 C 0.8860(3) 0.6433(3) 0.2077(2) 0.0183(5) Uani 1 1 d . . . . .
C16 C 0.9270(3) 0.7644(3) 0.1283(2) 0.0251(6) Uani 1 1 d . . . . .
H16 H 0.8677 0.8645 0.1218 0.030 Uiso 1 1 calc R . . . .
C17 C 1.0554(3) 0.7368(3) 0.0589(2) 0.0263(6) Uani 1 1 d . . . . .
H17 H 1.0817 0.8184 0.0061 0.032 Uiso 1 1 calc R . . . .
C18 C 1.1453(3) 0.5880(3) 0.0676(2) 0.0234(6) Uani 1 1 d . . . . .
H18 H 1.2311 0.5697 0.0207 0.028 Uiso 1 1 calc R . . . .
C19 C 1.1064(3) 0.4671(3) 0.1465(2) 0.0239(6) Uani 1 1 d . . . . .
H19 H 1.1664 0.3672 0.1532 0.029 Uiso 1 1 calc R . . . .
C20 C 0.9770(3) 0.4952(3) 0.2162(2) 0.0224(6) Uani 1 1 d . . . . .
H20 H 0.9513 0.4134 0.2691 0.027 Uiso 1 1 calc R . . . .
C21 C 0.6071(3) 0.6353(3) 0.2597(2) 0.0183(5) Uani 1 1 d . . . . .
C22 C 0.4778(3) 0.6398(3) 0.3335(2) 0.0179(5) Uani 1 1 d . . . . .
C23 C 0.4882(3) 0.6945(3) 0.4274(2) 0.0169(5) Uani 1 1 d . . . . .
C24 C 0.3552(3) 0.7040(3) 0.5011(2) 0.0177(5) Uani 1 1 d . . . . .
H1 H 0.461(4) 0.761(3) 0.652(3) 0.033(9) Uiso 1 1 d . . . . .
H3A H 0.341(4) 0.561(3) 0.257(3) 0.039(9) Uiso 1 1 d . . . . .
H3B H 0.264(4) 0.615(3) 0.362(3) 0.026(8) Uiso 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
O1 N2 1.225(3) . ?
O2 N2 1.235(3) . ?
N1 C6 1.392(3) . ?
N1 C8 1.378(3) . ?
N1 H1 0.86(3) . ?
N2 C21 1.450(3) . ?
N3 C22 1.363(3) . ?
N3 H3A 0.91(3) . ?
N3 H3B 0.88(3) . ?
N4 C24 1.149(3) . ?
C1 C2 1.422(3) . ?
C1 C6 1.444(3) . ?
C1 C23 1.410(3) . ?
C2 C3 1.508(3) . ?
C2 C14 1.397(4) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C3 C4 1.493(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.481(3) . ?
C5 C6 1.374(3) . ?
C5 C7 1.424(3) . ?
C7 C8 1.411(3) . ?
C7 C12 1.407(4) . ?
C8 C9 1.401(3) . ?
C9 C10 1.384(4) . ?
C9 C13 1.504(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.405(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.498(3) . ?
C14 C21 1.405(3) . ?
C15 C16 1.395(4) . ?
C15 C20 1.386(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.409(3) . ?
C22 C23 1.412(3) . ?
C23 C24 1.434(3) . ?

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
C6 N1 H1 125(2) . . ?
C8 N1 C6 108.7(2) . . ?
C8 N1 H1 126(2) . . ?
O1 N2 O2 123.1(2) . . ?
O1 N2 C21 118.5(2) . . ?
O2 N2 C21 118.4(2) . . ?
C22 N3 H3A 119.5(19) . . ?
C22 N3 H3B 119.1(19) . . ?
H3A N3 H3B 121(3) . . ?
C2 C1 C6 116.7(2) . . ?
C23 C1 C2 119.1(2) . . ?
C23 C1 C6 124.2(2) . . ?
C1 C2 C3 118.3(2) . . ?
C14 C2 C1 119.6(2) . . ?
C14 C2 C3 121.9(2) . . ?
C2 C3 H3C 108.7 . . ?
C2 C3 H3D 108.7 . . ?
H3C C3 H3D 107.6 . . ?
C4 C3 C2 114.4(2) . . ?
C4 C3 H3C 108.7 . . ?
C4 C3 H3D 108.7 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.1(2) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 C7 108.0(2) . . ?
C7 C5 C4 130.9(2) . . ?
N1 C6 C1 128.4(2) . . ?
C5 C6 N1 108.6(2) . . ?
C5 C6 C1 122.9(2) . . ?
C8 C7 C5 106.5(2) . . ?
C12 C7 C5 133.9(2) . . ?
C12 C7 C8 119.5(2) . . ?
N1 C8 C7 108.1(2) . . ?
N1 C8 C9 129.2(2) . . ?
C9 C8 C7 122.7(2) . . ?
C8 C9 C13 121.4(2) . . ?
C10 C9 C8 115.9(2) . . ?
C10 C9 C13 122.7(2) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.5(2) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 120.9 . . ?
C11 C12 C7 118.1(2) . . ?
C11 C12 H12 120.9 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 C15 120.8(2) . . ?
C2 C14 C21 119.6(2) . . ?
C21 C14 C15 119.4(2) . . ?
C16 C15 C14 121.2(2) . . ?
C20 C15 C14 120.1(2) . . ?
C20 C15 C16 118.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 121.0(2) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C14 C21 N2 119.2(2) . . ?
C14 C21 C22 122.9(2) . . ?
C22 C21 N2 117.8(2) . . ?
N3 C22 C21 123.9(2) . . ?
N3 C22 C23 120.0(2) . . ?
C21 C22 C23 116.1(2) . . ?
C1 C23 C22 122.6(2) . . ?
C1 C23 C24 120.8(2) . . ?
C22 C23 C24 116.6(2) . . ?
N4 C24 C23 177.6(3) . . ?

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
O1 N2 C21 C14 -43.0(3) . . . . ?
O1 N2 C21 C22 136.3(2) . . . . ?
O2 N2 C21 C14 137.9(2) . . . . ?
O2 N2 C21 C22 -42.8(3) . . . . ?
N1 C8 C9 C10 178.5(2) . . . . ?
N1 C8 C9 C13 -0.8(4) . . . . ?
N2 C21 C22 N3 4.3(4) . . . . ?
N2 C21 C22 C23 -174.3(2) . . . . ?
N3 C22 C23 C1 178.6(2) . . . . ?
N3 C22 C23 C24 -0.5(3) . . . . ?
C1 C2 C3 C4 -37.2(3) . . . . ?
C1 C2 C14 C15 -175.7(2) . . . . ?
C1 C2 C14 C21 -0.4(3) . . . . ?
C2 C1 C6 N1 -172.1(2) . . . . ?
C2 C1 C6 C5 12.4(3) . . . . ?
C2 C1 C23 C22 -0.8(4) . . . . ?
C2 C1 C23 C24 178.2(2) . . . . ?
C2 C3 C4 C5 46.4(3) . . . . ?
C2 C14 C15 C16 -76.1(3) . . . . ?
C2 C14 C15 C20 104.9(3) . . . . ?
C2 C14 C21 N2 175.8(2) . . . . ?
C2 C14 C21 C22 -3.4(4) . . . . ?
C3 C2 C14 C15 -0.4(4) . . . . ?
C3 C2 C14 C21 174.9(2) . . . . ?
C3 C4 C5 C6 -29.4(3) . . . . ?
C3 C4 C5 C7 153.2(3) . . . . ?
C4 C5 C6 N1 -176.4(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C7 C8 176.3(2) . . . . ?
C4 C5 C7 C12 -5.5(5) . . . . ?
C5 C7 C8 N1 0.6(3) . . . . ?
C5 C7 C8 C9 179.4(2) . . . . ?
C5 C7 C12 C11 -178.9(3) . . . . ?
C6 N1 C8 C7 0.3(3) . . . . ?
C6 N1 C8 C9 -178.4(2) . . . . ?
C6 C1 C2 C3 6.9(3) . . . . ?
C6 C1 C2 C14 -177.7(2) . . . . ?
C6 C1 C23 C22 179.3(2) . . . . ?
C6 C1 C23 C24 -1.6(4) . . . . ?
C6 C5 C7 C8 -1.4(3) . . . . ?
C6 C5 C7 C12 176.9(3) . . . . ?
C7 C5 C6 N1 1.5(3) . . . . ?
C7 C5 C6 C1 177.9(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C7 C8 C9 C13 -179.3(2) . . . . ?
C8 N1 C6 C1 -177.2(2) . . . . ?
C8 N1 C6 C5 -1.1(3) . . . . ?
C8 C7 C12 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C12 C7 C8 N1 -177.9(2) . . . . ?
C12 C7 C8 C9 0.9(4) . . . . ?
C13 C9 C10 C11 178.3(2) . . . . ?
C14 C2 C3 C4 147.5(2) . . . . ?
C14 C15 C16 C17 -178.6(2) . . . . ?
C14 C15 C20 C19 178.7(2) . . . . ?
C14 C21 C22 N3 -176.5(2) . . . . ?
C14 C21 C22 C23 4.9(3) . . . . ?
C15 C14 C21 N2 -8.9(3) . . . . ?
C15 C14 C21 C22 171.9(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C15 C20 C19 -0.4(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C21 C14 C15 C16 108.7(3) . . . . ?
C21 C14 C15 C20 -70.4(3) . . . . ?
C21 C22 C23 C1 -2.7(3) . . . . ?
C21 C22 C23 C24 178.2(2) . . . . ?
C23 C1 C2 C3 -173.0(2) . . . . ?
C23 C1 C2 C14 2.5(3) . . . . ?
C23 C1 C6 N1 7.8(4) . . . . ?
C23 C1 C6 C5 -167.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6697(14)
2 0.3303(14)
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9d
_database_code_depnum_ccdc_archive 'CCDC 1547597'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2016-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H16 N4 O2'
_chemical_formula_sum            'C23 H16 N4 O2'
_chemical_formula_weight         380.40
_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      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                   8.3973(8)
_cell_length_b                   8.5161(9)
_cell_length_c                   14.1035(13)
_cell_angle_alpha                97.848(6)
_cell_angle_beta                 104.222(6)
_cell_angle_gamma                108.609(6)
_cell_volume                     900.83(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1413 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7480.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.102
_diffrn_reflns_theta_min         1.532
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3070
_reflns_number_total             4340
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     275
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.077
_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)+(0.0617P)²+0.2521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          
;
Occupancies of the disordered fragment were fixed at refined values.
Restraints applied to maintain sensible thermal and geometric
parameters.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 C3-C2 \\sim C3A-C2A \\sim C6-C1A \\sim C6-C1
 with sigma of 0.01
 C2A-C1A \\sim C2-C1
 with sigma of 0.01
 C5-C4 \\sim C5-C4A \\sim C4A-C3A \\sim C4-C3 \\sim C3-C2 \\sim C3A-C2A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C4A \\sim C3A \\sim C1A \\sim C2A \\sim
C22A \\sim C22 \\sim C23A \\sim C23 \\sim N4A \\sim N4 \\sim C21A \\sim C21
\\sim N3A \\sim N3: within 2A with sigma of 0.003 and sigma for terminal atoms
of 0.006
4. Others
 Fixed Sof: N3(0.68973) H3A(0.68973) H3B(0.68973) N4(0.68973) C1(0.68973)
 C2(0.68973) C3(0.68973) H3C(0.68973) H3D(0.68973) C4(0.68973) H4A(0.68973)
 H4B(0.68973) C21(0.68973) C22(0.68973) C23(0.68973) C4A(0.31027) H4AA(0.31027)
 H4AB(0.31027) C3A(0.31027) H3AA(0.31027) H3AB(0.31027) C22A(0.31027)
 C21A(0.31027) N3A(0.31027) H3AC(0.31027) H3AD(0.31027) C23A(0.31027)
 N4A(0.31027) C1A(0.31027) C2A(0.31027)
5.a Rotating group:
 N3(H3A,H3B), N3A(H3AC,H3AD)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3C,H3D), C4(H4A,H4B), C4A(H4AA,H4AB), C3A(H3AA,H3AB)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.58876(16) 0.34139(18) 0.02667(9) 0.0321(3) Uani 1 1 d . . . . .
O2 O 0.6755(2) 0.13167(17) 0.04661(10) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.63691(18) 0.35860(18) 0.55209(10) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.5782 0.2505 0.5353 0.028 Uiso 1 1 calc R . . . .
N2 N 0.64534(18) 0.25716(19) 0.07993(10) 0.0252(3) Uani 1 1 d . . . . .
N3 N 0.4836(3) 0.0087(4) 0.1789(2) 0.0249(6) Uani 0.6897 1 d . U P A 1
H3A H 0.3874 -0.0294 0.1948 0.030 Uiso 0.6897 1 d GR . P A 1
H3B H 0.4557 0.0039 0.1150 0.030 Uiso 0.6897 1 d GR . P A 1
N4 N 0.3988(3) -0.0139(3) 0.39326(16) 0.0348(5) Uani 0.6897 1 d . U P A 1
C1 C 0.6950(7) 0.3910(8) 0.3884(3) 0.0194(6) Uani 0.6897 1 d D U P A 1
C2 C 0.7892(15) 0.5151(6) 0.3443(5) 0.0192(7) Uani 0.6897 1 d D U P A 1
C3 C 0.9171(4) 0.6854(4) 0.4090(2) 0.0238(6) Uani 0.6897 1 d D U P A 1
H3C H 0.9366 0.7657 0.3666 0.029 Uiso 0.6897 1 calc R . P A 1
H3D H 1.0292 0.6748 0.4388 0.029 Uiso 0.6897 1 calc R . P A 1
C4 C 0.8586(4) 0.7571(3) 0.4918(2) 0.0283(6) Uani 0.6897 1 d D U P A 1
H4A H 0.9562 0.8534 0.5389 0.034 Uiso 0.6897 1 calc R . P A 1
H4B H 0.7641 0.7957 0.4640 0.034 Uiso 0.6897 1 calc R . P A 1
C5 C 0.7962(3) 0.6214(2) 0.54358(13) 0.0299(4) Uani 1 1 d D . . . .
C6 C 0.7142(2) 0.4543(2) 0.49237(12) 0.0217(3) Uani 1 1 d D . . . .
C7 C 0.6700(2) 0.4653(2) 0.64243(12) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.7704(3) 0.6318(2) 0.64037(13) 0.0282(4) Uani 1 1 d . . . . .
C9 C 0.8205(3) 0.7646(3) 0.72505(14) 0.0421(5) Uani 1 1 d . . . . .
H9 H 0.8879 0.8754 0.7257 0.051 Uiso 1 1 calc R . . . .
C10 C 0.7683(3) 0.7280(3) 0.80718(14) 0.0357(5) Uani 1 1 d . . . . .
H10 H 0.8023 0.8152 0.8640 0.043 Uiso 1 1 calc R . . . .
C11 C 0.6649(2) 0.5623(2) 0.80711(13) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.6291 0.5420 0.8631 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6155(2) 0.4293(2) 0.72565(13) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.5481 0.3190 0.7258 0.031 Uiso 1 1 calc R . . . .
C13 C 0.7710(2) 0.4729(2) 0.24021(12) 0.0201(3) Uani 1 1 d . . . . .
C14 C 0.8559(2) 0.5975(2) 0.18601(12) 0.0217(3) Uani 1 1 d . . . . .
C15 C 0.8000(2) 0.7299(2) 0.16628(13) 0.0271(4) Uani 1 1 d . . . . .
H15 H 0.7115 0.7465 0.1903 0.033 Uiso 1 1 calc R . . . .
C16 C 0.8755(3) 0.8372(2) 0.11098(14) 0.0319(4) Uani 1 1 d . . . . .
H16 H 0.8371 0.9252 0.0974 0.038 Uiso 1 1 calc R . . . .
C17 C 1.0088(2) 0.8132(2) 0.07571(14) 0.0316(4) Uani 1 1 d . . . . .
H17 H 1.0592 0.8849 0.0382 0.038 Uiso 1 1 calc R . . . .
C18 C 1.0663(2) 0.6837(2) 0.09607(13) 0.0291(4) Uani 1 1 d . . . . .
H18 H 1.1566 0.6689 0.0732 0.035 Uiso 1 1 calc R . . . .
C19 C 0.9895(2) 0.5749(2) 0.15092(13) 0.0255(4) Uani 1 1 d . . . . .
H19 H 1.0278 0.4867 0.1641 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6757(2) 0.3036(2) 0.18811(12) 0.0235(4) Uani 1 1 d . . . . .
C21 C 0.5800(4) 0.1731(6) 0.2302(3) 0.0220(7) Uani 0.6897 1 d . U P A 1
C22 C 0.5918(4) 0.2264(4) 0.3316(3) 0.0222(6) Uani 0.6897 1 d . U P A 1
C23 C 0.4872(4) 0.0979(3) 0.37040(18) 0.0239(5) Uani 0.6897 1 d . U P A 1
C4A C 0.9336(8) 0.7454(7) 0.5057(4) 0.0215(9) Uani 0.3103 1 d D U P A 2
H4AA H 0.9532 0.8623 0.5353 0.026 Uiso 0.3103 1 calc R . P A 2
H4AB H 1.0452 0.7291 0.5257 0.026 Uiso 0.3103 1 calc R . P A 2
C3A C 0.8663(9) 0.7119(9) 0.3937(4) 0.0239(9) Uani 0.3103 1 d D U P A 2
H3AA H 0.9629 0.7710 0.3701 0.029 Uiso 0.3103 1 calc R . P A 2
H3AB H 0.7770 0.7614 0.3764 0.029 Uiso 0.3103 1 calc R . P A 2
C22A C 0.6499(9) 0.2283(11) 0.3381(6) 0.0224(8) Uani 0.3103 1 d . U P A 2
C21A C 0.6314(10) 0.1763(14) 0.2349(8) 0.0227(11) Uani 0.3103 1 d . U P A 2
N3A N 0.5580(8) 0.0061(9) 0.1898(6) 0.0291(13) Uani 0.3103 1 d . U P A 2
H3AC H 0.4694 -0.0466 0.2106 0.035 Uiso 0.3103 1 d GR . P A 2
H3AD H 0.5164 -0.0083 0.1246 0.035 Uiso 0.3103 1 d GR . P A 2
C23A C 0.6017(9) 0.0935(7) 0.3862(4) 0.0286(9) Uani 0.3103 1 d . U P A 2
N4A N 0.5632(8) -0.0266(7) 0.4172(4) 0.0419(12) Uani 0.3103 1 d . U P A 2
C1A C 0.7200(17) 0.405(2) 0.3892(6) 0.0209(10) Uani 0.3103 1 d D U P A 2
C2A C 0.789(3) 0.5291(12) 0.3378(11) 0.0203(10) Uani 0.3103 1 d D U 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 N2 1.2221(18) . ?
O2 N2 1.2335(19) . ?
N1 H1 0.8600 . ?
N1 C6 1.3833(19) . ?
N1 C7 1.369(2) . ?
N2 C20 1.459(2) . ?
N3 H3A 0.8661 . ?
N3 H3B 0.8655 . ?
N3 C21 1.360(5) . ?
N4 C23 1.145(3) . ?
C1 C2 1.420(4) . ?
C1 C6 1.442(4) . ?
C1 C22 1.391(6) . ?
C2 C3 1.501(5) . ?
C2 C13 1.421(7) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C3 C4 1.502(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.475(3) . ?
C5 C6 1.367(2) . ?
C5 C8 1.429(2) . ?
C5 C4A 1.553(5) . ?
C6 C1A 1.476(7) . ?
C7 C8 1.408(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.401(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.401(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.491(2) . ?
C13 C20 1.395(2) . ?
C13 C2A 1.349(15) . ?
C14 C15 1.389(2) . ?
C14 C19 1.388(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.442(5) . ?
C20 C21A 1.345(12) . ?
C21 C22 1.409(5) . ?
C22 C23 1.433(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C3A 1.493(6) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C2A 1.494(7) . ?
C22A C21A 1.416(12) . ?
C22A C23A 1.412(10) . ?
C22A C1A 1.434(16) . ?
C21A N3A 1.367(12) . ?
N3A H3AC 0.8784 . ?
N3A H3AD 0.8752 . ?
C23A N4A 1.150(7) . ?
C1A C2A 1.416(8) . ?

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
C6 N1 H1 125.8 . . ?
C7 N1 H1 125.8 . . ?
C7 N1 C6 108.32(13) . . ?
O1 N2 O2 123.21(15) . . ?
O1 N2 C20 119.05(14) . . ?
O2 N2 C20 117.72(14) . . ?
H3A N3 H3B 108.6 . . ?
C21 N3 H3A 110.5 . . ?
C21 N3 H3B 109.2 . . ?
C2 C1 C6 113.9(5) . . ?
C22 C1 C2 120.5(3) . . ?
C22 C1 C6 125.5(4) . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 C13 119.6(3) . . ?
C13 C2 C3 120.2(5) . . ?
C2 C3 H3C 108.6 . . ?
C2 C3 H3D 108.6 . . ?
C2 C3 C4 114.5(5) . . ?
H3C C3 H3D 107.6 . . ?
C4 C3 H3C 108.6 . . ?
C4 C3 H3D 108.6 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 108.1(2) . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C6 C5 C4 121.17(17) . . ?
C6 C5 C8 107.11(14) . . ?
C6 C5 C4A 119.3(3) . . ?
C8 C5 C4 130.33(18) . . ?
C8 C5 C4A 130.9(3) . . ?
N1 C6 C1 125.1(3) . . ?
N1 C6 C1A 131.2(6) . . ?
C5 C6 N1 109.63(14) . . ?
C5 C6 C1 125.0(3) . . ?
C5 C6 C1A 119.2(6) . . ?
N1 C7 C8 108.46(14) . . ?
N1 C7 C12 129.62(16) . . ?
C12 C7 C8 121.90(16) . . ?
C7 C8 C5 106.49(15) . . ?
C9 C8 C5 134.45(17) . . ?
C9 C8 C7 119.06(16) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.75(18) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.46(18) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.04(16) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 121.1 . . ?
C11 C12 C7 117.76(16) . . ?
C11 C12 H12 121.1 . . ?
C2 C13 C14 123.5(2) . . ?
C20 C13 C2 117.5(2) . . ?
C20 C13 C14 118.91(14) . . ?
C2A C13 C14 118.5(5) . . ?
C2A C13 C20 122.6(5) . . ?
C15 C14 C13 121.95(14) . . ?
C19 C14 C13 118.47(15) . . ?
C19 C14 C15 119.52(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.26(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.84(17) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.22(16) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.96(16) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.20(17) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C13 C20 N2 119.12(14) . . ?
C13 C20 C21 124.3(2) . . ?
C21 C20 N2 115.9(2) . . ?
C21A C20 N2 117.6(5) . . ?
C21A C20 C13 122.6(5) . . ?
N3 C21 C20 124.4(4) . . ?
N3 C21 C22 120.4(3) . . ?
C22 C21 C20 115.2(3) . . ?
C1 C22 C21 122.4(3) . . ?
C1 C22 C23 123.1(3) . . ?
C21 C22 C23 114.4(3) . . ?
N4 C23 C22 174.0(3) . . ?
C5 C4A H4AA 109.8 . . ?
C5 C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.3 . . ?
C3A C4A C5 109.3(4) . . ?
C3A C4A H4AA 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
C4A C3A H3AA 108.2 . . ?
C4A C3A H3AB 108.2 . . ?
C4A C3A C2A 116.3(8) . . ?
H3AA C3A H3AB 107.4 . . ?
C2A C3A H3AA 108.2 . . ?
C2A C3A H3AB 108.2 . . ?
C21A C22A C1A 121.8(8) . . ?
C23A C22A C21A 114.7(7) . . ?
C23A C22A C1A 123.5(8) . . ?
C20 C21A C22A 115.2(8) . . ?
C20 C21A N3A 125.7(9) . . ?
N3A C21A C22A 118.9(8) . . ?
C21A N3A H3AC 111.4 . . ?
C21A N3A H3AD 109.9 . . ?
H3AC N3A H3AD 107.3 . . ?
N4A C23A C22A 173.1(7) . . ?
C22A C1A C6 119.9(10) . . ?
C2A C1A C6 121.2(13) . . ?
C2A C1A C22A 118.9(7) . . ?
C13 C2A C3A 125.2(10) . . ?
C13 C2A C1A 116.9(7) . . ?
C1A C2A C3A 117.9(13) . . ?

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
O1 N2 C20 C13 -49.2(2) . . . . ?
O1 N2 C20 C21 121.5(2) . . . . ?
O1 N2 C20 C21A 139.9(4) . . . . ?
O2 N2 C20 C13 132.07(17) . . . . ?
O2 N2 C20 C21 -57.2(2) . . . . ?
O2 N2 C20 C21A -38.8(4) . . . . ?
N1 C6 C1A C22A -6.0(17) . . . . ?
N1 C6 C1A C2A 172.0(15) . . . . ?
N1 C7 C8 C5 0.31(19) . . . . ?
N1 C7 C8 C9 179.84(17) . . . . ?
N1 C7 C12 C11 -178.70(16) . . . . ?
N2 C20 C21 N3 8.3(4) . . . . ?
N2 C20 C21 C22 -171.8(2) . . . . ?
N2 C20 C21A C22A -175.0(4) . . . . ?
N2 C20 C21A N3A -0.9(9) . . . . ?
N3 C21 C22 C1 177.1(4) . . . . ?
N3 C21 C22 C23 -3.8(4) . . . . ?
C1 C2 C3 C4 -38.3(11) . . . . ?
C1 C2 C13 C14 176.2(7) . . . . ?
C1 C2 C13 C20 -7.1(12) . . . . ?
C1 C2 C13 C2A 143(17) . . . . ?
C1 C6 C1A C22A -47(7) . . . . ?
C1 C6 C1A C2A 131(9) . . . . ?
C2 C1 C6 N1 -179.5(6) . . . . ?
C2 C1 C6 C5 7.6(9) . . . . ?
C2 C1 C6 C1A -36(7) . . . . ?
C2 C1 C22 C21 2.1(10) . . . . ?
C2 C1 C22 C23 -177.0(7) . . . . ?
C2 C3 C4 C5 47.5(5) . . . . ?
C2 C13 C14 C15 -70.4(6) . . . . ?
C2 C13 C14 C19 112.3(6) . . . . ?
C2 C13 C20 N2 176.4(6) . . . . ?
C2 C13 C20 C21 6.6(6) . . . . ?
C2 C13 C20 C21A -13.2(7) . . . . ?
C2 C13 C2A C3A 158(18) . . . . ?
C2 C13 C2A C1A -26(14) . . . . ?
C3 C2 C13 C14 -8.3(11) . . . . ?
C3 C2 C13 C20 168.4(6) . . . . ?
C3 C2 C13 C2A -41(15) . . . . ?
C3 C4 C5 C6 -33.4(3) . . . . ?
C3 C4 C5 C8 161.8(2) . . . . ?
C3 C4 C5 C4A 59.8(6) . . . . ?
C4 C5 C6 N1 -167.6(2) . . . . ?
C4 C5 C6 C1 6.2(5) . . . . ?
C4 C5 C6 C1A 12.5(8) . . . . ?
C4 C5 C8 C7 166.0(2) . . . . ?
C4 C5 C8 C9 -13.4(4) . . . . ?
C4 C5 C4A C3A -59.3(6) . . . . ?
C5 C6 C1A C22A 173.9(8) . . . . ?
C5 C6 C1A C2A -8(2) . . . . ?
C5 C8 C9 C10 178.7(2) . . . . ?
C5 C4A C3A C2A -45.3(14) . . . . ?
C6 N1 C7 C8 -0.15(18) . . . . ?
C6 N1 C7 C12 178.04(16) . . . . ?
C6 C1 C2 C3 9.1(13) . . . . ?
C6 C1 C2 C13 -175.3(6) . . . . ?
C6 C1 C22 C21 -179.7(4) . . . . ?
C6 C1 C22 C23 1.2(8) . . . . ?
C6 C5 C8 C7 -0.4(2) . . . . ?
C6 C5 C8 C9 -179.8(2) . . . . ?
C6 C5 C4A C3A 42.1(6) . . . . ?
C6 C1A C2A C13 -172.9(14) . . . . ?
C6 C1A C2A C3A 4(3) . . . . ?
C7 N1 C6 C1 -173.9(4) . . . . ?
C7 N1 C6 C5 -0.08(19) . . . . ?
C7 N1 C6 C1A 179.8(9) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C5 C6 N1 0.3(2) . . . . ?
C8 C5 C6 C1 174.1(4) . . . . ?
C8 C5 C6 C1A -179.7(8) . . . . ?
C8 C5 C4A C3A -159.1(4) . . . . ?
C8 C7 C12 C11 -0.7(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C12 C7 C8 C5 -178.05(16) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C13 C2 C3 C4 146.1(7) . . . . ?
C13 C14 C15 C16 -176.42(17) . . . . ?
C13 C14 C19 C18 177.07(16) . . . . ?
C13 C20 C21 N3 178.5(2) . . . . ?
C13 C20 C21 C22 -1.7(4) . . . . ?
C13 C20 C21A C22A 14.5(8) . . . . ?
C13 C20 C21A N3A -171.4(6) . . . . ?
C14 C13 C20 N2 -6.7(2) . . . . ?
C14 C13 C20 C21 -176.6(2) . . . . ?
C14 C13 C20 C21A 163.7(4) . . . . ?
C14 C13 C2A C3A 9(3) . . . . ?
C14 C13 C2A C1A -174.7(16) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C19 C14 C15 C16 0.8(3) . . . . ?
C20 C13 C14 C15 112.90(19) . . . . ?
C20 C13 C14 C19 -64.4(2) . . . . ?
C20 C13 C2A C3A -170.7(15) . . . . ?
C20 C13 C2A C1A 6(3) . . . . ?
C20 C21 C22 C1 -2.8(5) . . . . ?
C20 C21 C22 C23 176.3(3) . . . . ?
C21 C20 C21A C22A -87(2) . . . . ?
C21 C20 C21A N3A 87(2) . . . . ?
C22 C1 C2 C3 -172.5(6) . . . . ?
C22 C1 C2 C13 3.0(14) . . . . ?
C22 C1 C6 N1 2.2(8) . . . . ?
C22 C1 C6 C5 -170.7(4) . . . . ?
C22 C1 C6 C1A 145(9) . . . . ?
C4A C5 C6 N1 163.6(3) . . . . ?
C4A C5 C6 C1 -22.5(5) . . . . ?
C4A C5 C6 C1A -16.3(8) . . . . ?
C4A C5 C8 C7 -161.1(3) . . . . ?
C4A C5 C8 C9 19.5(5) . . . . ?
C4A C3A C2A C13 -158.7(18) . . . . ?
C4A C3A C2A C1A 25(3) . . . . ?
C22A C1A C2A C13 5(3) . . . . ?
C22A C1A C2A C3A -178.2(14) . . . . ?
C21A C20 C21 N3 -92(2) . . . . ?
C21A C20 C21 C22 88(2) . . . . ?
C21A C22A C1A C6 171.5(9) . . . . ?
C21A C22A C1A C2A -7(2) . . . . ?
C23A C22A C21A C20 179.5(6) . . . . ?
C23A C22A C21A N3A 5.0(10) . . . . ?
C23A C22A C1A C6 -11.5(16) . . . . ?
C23A C22A C1A C2A 170.4(17) . . . . ?
C1A C22A C21A C20 -3.2(12) . . . . ?
C1A C22A C21A N3A -177.8(9) . . . . ?
C2A C13 C14 C15 -66.8(14) . . . . ?
C2A C13 C14 C19 116.0(14) . . . . ?
C2A C13 C20 N2 173.0(14) . . . . ?
C2A C13 C20 C21 3.1(15) . . . . ?
C2A C13 C20 C21A -16.7(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
