# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2161404'
loop_
_audit_author_name
_audit_author_address
'Julia Voronina'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N4 O2'
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.659(3)
_cell_length_b                   18.266(5)
_cell_length_c                   10.132(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.345(10)
_cell_angle_gamma                90
_cell_volume                     1641.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1333
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1113 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.8688.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11447
_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         25.999
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2043
_reflns_number_total             3235
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.014
_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)+(0.0382P)²+0.5360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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
O2 O 0.3446(2) 0.40527(9) 0.25646(18) 0.0249(4) Uani 1 1 d . . . . .
O12 O 1.0818(2) 0.56415(9) 0.81371(18) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.6044(2) 0.39039(10) 0.3668(2) 0.0188(5) Uani 1 1 d . . . . .
N3 N 0.5121(2) 0.50118(11) 0.2860(2) 0.0202(5) Uani 1 1 d . . . . .
N11 N 0.8824(2) 0.52376(10) 0.6067(2) 0.0180(5) Uani 1 1 d . . . . .
N13 N 0.9654(2) 0.45238(10) 0.7993(2) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.4734(3) 0.42936(13) 0.2987(3) 0.0190(6) Uani 1 1 d . . . . .
C4 C 0.6727(3) 0.50532(13) 0.3133(3) 0.0185(5) Uani 1 1 d . . . . .
H4 H 0.685084 0.495928 0.221310 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7453(3) 0.57813(13) 0.3743(3) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.7138(3) 0.63909(14) 0.2841(3) 0.0252(6) Uani 1 1 d . . . . .
H6 H 0.649206 0.633622 0.185590 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7742(3) 0.70747(14) 0.3345(3) 0.0274(7) Uani 1 1 d . . . . .
H7 H 0.751535 0.748400 0.271638 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8684(3) 0.71484(14) 0.4789(3) 0.0273(7) Uani 1 1 d . . . . .
H8 H 0.908627 0.761609 0.515156 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9048(3) 0.65528(13) 0.5707(3) 0.0232(6) Uani 1 1 d . . . . .
H9 H 0.970616 0.661066 0.668829 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8442(3) 0.58650(13) 0.5184(3) 0.0191(6) Uani 1 1 d . . . . .
C12 C 0.9864(3) 0.51843(13) 0.7480(3) 0.0204(6) Uani 1 1 d . . . . .
C14 C 0.8708(3) 0.40519(13) 0.6822(3) 0.0199(6) Uani 1 1 d . . . . .
H14A H 0.804837 0.373737 0.712117 0.024 Uiso 1 1 calc R U . . .
H14B H 0.932135 0.374017 0.646231 0.024 Uiso 1 1 calc R U . . .
C15 C 0.7793(3) 0.46140(12) 0.5698(3) 0.0186(6) Uani 1 1 d . . . . .
H15 H 0.686749 0.474692 0.585944 0.022 Uiso 1 1 calc R U . . .
C16 C 0.7348(3) 0.43975(12) 0.4135(3) 0.0185(6) Uani 1 1 d . . . . .
H16 H 0.821613 0.416870 0.398645 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6124(3) 0.32066(13) 0.4329(3) 0.0198(6) Uani 1 1 d . . . . .
C18 C 0.7299(3) 0.27415(13) 0.4421(3) 0.0211(6) Uani 1 1 d . . . . .
H18 H 0.796693 0.287552 0.398152 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7495(3) 0.20838(13) 0.5151(3) 0.0219(6) Uani 1 1 d . . . . .
H19 H 0.831444 0.177269 0.523628 0.026 Uiso 1 1 calc R U . . .
C20 C 0.6493(3) 0.18799(13) 0.5757(3) 0.0222(6) Uani 1 1 d . . . . .
H20 H 0.662232 0.142783 0.625509 0.027 Uiso 1 1 calc R U . . .
C21 C 0.5305(3) 0.23354(13) 0.5635(3) 0.0230(6) Uani 1 1 d . . . . .
H21 H 0.460762 0.218832 0.603173 0.028 Uiso 1 1 calc R U . . .
C22 C 0.5121(3) 0.30039(13) 0.4941(3) 0.0211(6) Uani 1 1 d . . . . .
H22 H 0.431921 0.332059 0.488321 0.025 Uiso 1 1 calc R U . . .
C23 C 0.4045(3) 0.54734(13) 0.1766(3) 0.0241(6) Uani 1 1 d . . . . .
H23A H 0.418526 0.542038 0.086422 0.036 Uiso 1 1 calc R U . . .
H23B H 0.420588 0.598535 0.207908 0.036 Uiso 1 1 calc R U . . .
H23C H 0.301782 0.532597 0.161549 0.036 Uiso 1 1 calc R U . . .
C24 C 1.0772(3) 0.42217(14) 0.9307(3) 0.0245(6) Uani 1 1 d . . . . .
H24A H 1.138063 0.385705 0.906776 0.037 Uiso 1 1 calc R U . . .
H24B H 1.026479 0.398881 0.986457 0.037 Uiso 1 1 calc R U . . .
H24C H 1.142745 0.461531 0.987559 0.037 Uiso 1 1 calc R U . . .


_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
O2 C2 1.226(3) . ?
O12 C12 1.227(3) . ?
N1 C2 1.376(3) . ?
N1 C16 1.467(3) . ?
N1 C17 1.427(3) . ?
N3 C2 1.384(3) . ?
N3 C4 1.467(3) . ?
N3 C23 1.451(3) . ?
N11 C10 1.410(3) . ?
N11 C12 1.388(3) . ?
N11 C15 1.461(3) . ?
N13 C12 1.360(3) . ?
N13 C14 1.458(3) . ?
N13 C24 1.451(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.516(3) . ?
C4 C16 1.531(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.401(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.528(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.520(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.391(3) . ?
C17 C22 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C2 N1 C16 110.22(19) . . ?
C2 N1 C17 124.4(2) . . ?
C17 N1 C16 121.2(2) . . ?
C2 N3 C4 109.6(2) . . ?
C2 N3 C23 118.9(2) . . ?
C23 N3 C4 119.84(19) . . ?
C10 N11 C15 119.4(2) . . ?
C12 N11 C10 127.7(2) . . ?
C12 N11 C15 110.52(19) . . ?
C12 N13 C14 110.7(2) . . ?
C12 N13 C24 121.2(2) . . ?
C24 N13 C14 121.37(19) . . ?
O2 C2 N1 126.4(2) . . ?
O2 C2 N3 125.6(2) . . ?
N1 C2 N3 108.0(2) . . ?
N3 C4 H4 108.9 . . ?
N3 C4 C5 113.9(2) . . ?
N3 C4 C16 101.06(18) . . ?
C5 C4 H4 108.9 . . ?
C5 C4 C16 114.8(2) . . ?
C16 C4 H4 108.9 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 C10 118.5(2) . . ?
C10 C5 C4 122.3(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.6(2) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 N11 118.1(2) . . ?
C9 C10 N11 121.6(2) . . ?
C9 C10 C5 120.2(2) . . ?
O12 C12 N11 126.4(2) . . ?
O12 C12 N13 126.2(2) . . ?
N13 C12 N11 107.4(2) . . ?
N13 C14 H14A 111.5 . . ?
N13 C14 H14B 111.5 . . ?
N13 C14 C15 101.54(19) . . ?
H14A C14 H14B 109.3 . . ?
C15 C14 H14A 111.5 . . ?
C15 C14 H14B 111.5 . . ?
N11 C15 C14 101.5(2) . . ?
N11 C15 H15 109.4 . . ?
N11 C15 C16 110.60(19) . . ?
C14 C15 H15 109.4 . . ?
C16 C15 C14 116.3(2) . . ?
C16 C15 H15 109.4 . . ?
N1 C16 C4 101.9(2) . . ?
N1 C16 C15 110.36(19) . . ?
N1 C16 H16 111.0 . . ?
C4 C16 H16 111.0 . . ?
C15 C16 C4 111.25(19) . . ?
C15 C16 H16 111.0 . . ?
C18 C17 N1 117.9(2) . . ?
C18 C17 C22 120.1(2) . . ?
C22 C17 N1 121.9(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.3(2) . . ?
C21 C22 H22 120.4 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N13 C24 H24A 109.5 . . ?
N13 C24 H24B 109.5 . . ?
N13 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 C17 C18 C19 174.9(2) . . . . ?
N1 C17 C22 C21 -176.5(2) . . . . ?
N3 C4 C5 C6 -74.0(3) . . . . ?
N3 C4 C5 C10 106.4(3) . . . . ?
N3 C4 C16 N1 28.8(2) . . . . ?
N3 C4 C16 C15 -88.8(2) . . . . ?
N11 C15 C16 N1 -165.80(19) . . . . ?
N11 C15 C16 C4 -53.5(3) . . . . ?
N13 C14 C15 N11 27.4(2) . . . . ?
N13 C14 C15 C16 147.4(2) . . . . ?
C2 N1 C16 C4 -22.3(2) . . . . ?
C2 N1 C16 C15 96.0(2) . . . . ?
C2 N1 C17 C18 152.9(2) . . . . ?
C2 N1 C17 C22 -30.6(4) . . . . ?
C2 N3 C4 C5 -151.3(2) . . . . ?
C2 N3 C4 C16 -27.7(2) . . . . ?
C4 N3 C2 O2 -165.2(2) . . . . ?
C4 N3 C2 N1 14.9(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C4 C5 C10 N11 3.2(3) . . . . ?
C4 C5 C10 C9 -178.1(2) . . . . ?
C5 C4 C16 N1 151.88(19) . . . . ?
C5 C4 C16 C15 34.3(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C5 C10 N11 -176.4(2) . . . . ?
C6 C5 C10 C9 2.4(4) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 N11 177.7(2) . . . . ?
C8 C9 C10 C5 -1.0(4) . . . . ?
C10 N11 C12 O12 -13.1(4) . . . . ?
C10 N11 C12 N13 168.2(2) . . . . ?
C10 N11 C15 C14 174.62(19) . . . . ?
C10 N11 C15 C16 50.6(3) . . . . ?
C10 C5 C6 C7 -1.9(4) . . . . ?
C12 N11 C10 C5 174.5(2) . . . . ?
C12 N11 C10 C9 -4.2(4) . . . . ?
C12 N11 C15 C14 -21.5(2) . . . . ?
C12 N11 C15 C16 -145.5(2) . . . . ?
C12 N13 C14 C15 -26.3(3) . . . . ?
C14 N13 C12 O12 -165.0(2) . . . . ?
C14 N13 C12 N11 13.6(3) . . . . ?
C14 C15 C16 N1 79.2(3) . . . . ?
C14 C15 C16 C4 -168.5(2) . . . . ?
C15 N11 C10 C5 -24.8(3) . . . . ?
C15 N11 C10 C9 156.5(2) . . . . ?
C15 N11 C12 O12 -175.3(2) . . . . ?
C15 N11 C12 N13 6.1(3) . . . . ?
C16 N1 C2 O2 -174.3(2) . . . . ?
C16 N1 C2 N3 5.6(3) . . . . ?
C16 N1 C17 C18 -52.4(3) . . . . ?
C16 N1 C17 C22 124.1(3) . . . . ?
C16 C4 C5 C6 170.1(2) . . . . ?
C16 C4 C5 C10 -9.4(3) . . . . ?
C17 N1 C2 O2 -17.3(4) . . . . ?
C17 N1 C2 N3 162.7(2) . . . . ?
C17 N1 C16 C4 179.81(19) . . . . ?
C17 N1 C16 C15 -61.9(3) . . . . ?
C17 C18 C19 C20 1.8(4) . . . . ?
C18 C17 C22 C21 -0.2(4) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C22 -1.5(4) . . . . ?
C20 C21 C22 C17 1.7(4) . . . . ?
C22 C17 C18 C19 -1.6(4) . . . . ?
C23 N3 C2 O2 -22.0(3) . . . . ?
C23 N3 C2 N1 158.1(2) . . . . ?
C23 N3 C4 C5 65.8(3) . . . . ?
C23 N3 C4 C16 -170.5(2) . . . . ?
C24 N13 C12 O12 -13.4(4) . . . . ?
C24 N13 C12 N11 165.2(2) . . . . ?
C24 N13 C14 C15 -177.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2161407'
loop_
_audit_author_name
_audit_author_address
'Julia Voronina'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N4 O4'
_chemical_formula_sum            'C22 H24 N4 O4'
_chemical_formula_weight         408.45
_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                   9.7783(9)
_cell_length_b                   11.9953(10)
_cell_length_c                   17.4364(15)
_cell_angle_alpha                81.427(3)
_cell_angle_beta                 83.627(4)
_cell_angle_gamma                70.331(3)
_cell_volume                     1900.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4759
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0600 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9012.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14765
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5288
_reflns_number_total             7401
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         7401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.030
_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)+(0.0560P)²+0.5166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1386
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C4A(H4A), C15A(H15A), C16A(H16A), C4B(H4B), C15B(H15B), C16B(H16B)
2.b Secondary CH2 refined with riding coordinates:
 C14A(H14A,H14B), C14B(H14C,H14D)
2.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C8A(H8A), C9A(H9A), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A),
 C6B(H6B), C8B(H8B), C9B(H9B), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B)
2.d Idealised Me refined as rotating group:
 C23A(H23A,H23B,H23C), C24A(H24A,H24B,H24C), C25A(H25A,H25B,H25C), C26A(H26A,
 H26B,H26C), C23B(H23D,H23E,H23F), C24B(H24D,H24E,H24F), C25B(H25D,H25E,H25F),
 C26B(H26D,H26E,H26F)
;
_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
O2A O 0.06152(18) 0.35136(15) 0.90026(9) 0.0191(4) Uani 1 1 d . . . . .
O7A O 0.13268(19) -0.01360(15) 0.55680(10) 0.0227(4) Uani 1 1 d . . . . .
O12A O 0.23424(18) 0.50303(15) 0.56248(10) 0.0206(4) Uani 1 1 d . . . . .
O20A O -0.43739(19) 0.85459(15) 0.95054(10) 0.0226(4) Uani 1 1 d . . . . .
N1A N -0.1151(2) 0.44526(17) 0.81041(11) 0.0146(4) Uani 1 1 d . . . . .
N3A N 0.0505(2) 0.27036(17) 0.79058(11) 0.0141(4) Uani 1 1 d . . . . .
N11A N 0.0530(2) 0.43853(17) 0.63338(11) 0.0142(4) Uani 1 1 d . . . . .
N13A N 0.0274(2) 0.63112(17) 0.61818(11) 0.0173(5) Uani 1 1 d . . . . .
C2A C 0.0034(3) 0.3546(2) 0.84043(13) 0.0151(5) Uani 1 1 d . . . . .
C4A C -0.0576(3) 0.2877(2) 0.73427(13) 0.0137(5) Uani 1 1 d . . . . .
H4A H -0.122387 0.239244 0.754360 0.016 Uiso 1 1 calc R U . . .
C5A C 0.0183(3) 0.2497(2) 0.65747(13) 0.0138(5) Uani 1 1 d . . . . .
C6A C 0.0362(3) 0.1381(2) 0.63761(13) 0.0162(5) Uani 1 1 d . . . . .
H6A H -0.009856 0.087807 0.669470 0.019 Uiso 1 1 calc R U . . .
C7A C 0.1216(3) 0.0986(2) 0.57107(14) 0.0165(5) Uani 1 1 d . . . . .
C8A C 0.1891(3) 0.1726(2) 0.52503(14) 0.0176(5) Uani 1 1 d . . . . .
H8A H 0.248842 0.145505 0.480283 0.021 Uiso 1 1 calc R U . . .
C9A C 0.1702(3) 0.2859(2) 0.54371(14) 0.0172(5) Uani 1 1 d . . . . .
H9A H 0.215876 0.336135 0.511575 0.021 Uiso 1 1 calc R U . . .
C10A C 0.0840(3) 0.3250(2) 0.60970(13) 0.0135(5) Uani 1 1 d . . . . .
C12A C 0.1170(3) 0.5239(2) 0.60022(14) 0.0167(5) Uani 1 1 d . . . . .
C14A C -0.0916(3) 0.6203(2) 0.67375(14) 0.0173(5) Uani 1 1 d . . . . .
H14A H -0.184159 0.683959 0.660945 0.021 Uiso 1 1 calc R U . . .
H14B H -0.070222 0.623255 0.727450 0.021 Uiso 1 1 calc R U . . .
C15A C -0.0975(3) 0.4976(2) 0.66357(14) 0.0146(5) Uani 1 1 d . . . . .
H15A H -0.163936 0.508331 0.621443 0.018 Uiso 1 1 calc R U . . .
C16A C -0.1448(3) 0.4220(2) 0.73482(13) 0.0134(5) Uani 1 1 d . . . . .
H16A H -0.250965 0.434141 0.734085 0.016 Uiso 1 1 calc R U . . .
C17A C -0.2018(3) 0.5469(2) 0.84674(13) 0.0140(5) Uani 1 1 d . . . . .
C18A C -0.3250(3) 0.6271(2) 0.81317(14) 0.0160(5) Uani 1 1 d . . . . .
H18A H -0.353839 0.611494 0.766709 0.019 Uiso 1 1 calc R U . . .
C19A C -0.4072(3) 0.7301(2) 0.84615(14) 0.0174(5) Uani 1 1 d . . . . .
H19A H -0.491042 0.783678 0.822060 0.021 Uiso 1 1 calc R U . . .
C20A C -0.3672(3) 0.7546(2) 0.91388(14) 0.0168(5) Uani 1 1 d . . . . .
C21A C -0.2469(3) 0.6733(2) 0.94905(13) 0.0163(5) Uani 1 1 d . . . . .
H21A H -0.220392 0.688279 0.996352 0.020 Uiso 1 1 calc R U . . .
C22A C -0.1647(3) 0.5709(2) 0.91678(13) 0.0150(5) Uani 1 1 d . . . . .
H22A H -0.082788 0.516531 0.942042 0.018 Uiso 1 1 calc R U . . .
C23A C 0.1461(3) 0.1513(2) 0.81624(14) 0.0194(6) Uani 1 1 d . . . . .
H23A H 0.199786 0.154896 0.859533 0.029 Uiso 1 1 calc R U . . .
H23B H 0.214940 0.120217 0.773120 0.029 Uiso 1 1 calc R U . . .
H23C H 0.087811 0.098686 0.833373 0.029 Uiso 1 1 calc R U . . .
C24A C 0.0767(3) 0.7336(2) 0.61089(15) 0.0217(6) Uani 1 1 d . . . . .
H24A H 0.070403 0.759680 0.662203 0.032 Uiso 1 1 calc R U . . .
H24B H 0.015160 0.798587 0.576177 0.032 Uiso 1 1 calc R U . . .
H24C H 0.177843 0.711895 0.589357 0.032 Uiso 1 1 calc R U . . .
C25A C 0.2062(3) -0.0515(2) 0.48462(15) 0.0235(6) Uani 1 1 d . . . . .
H25A H 0.160480 0.006653 0.441474 0.035 Uiso 1 1 calc R U . . .
H25B H 0.199486 -0.129560 0.479040 0.035 Uiso 1 1 calc R U . . .
H25C H 0.308707 -0.057458 0.484030 0.035 Uiso 1 1 calc R U . . .
C26A C -0.5666(3) 0.9372(2) 0.91857(16) 0.0277(7) Uani 1 1 d . . . . .
H26A H -0.543632 0.967770 0.865122 0.042 Uiso 1 1 calc R U . . .
H26B H -0.606107 1.003658 0.950001 0.042 Uiso 1 1 calc R U . . .
H26C H -0.638820 0.896993 0.918650 0.042 Uiso 1 1 calc R U . . .
O2B O 0.51497(19) 0.58473(15) 0.64257(10) 0.0209(4) Uani 1 1 d . . . . .
O7B O 0.61021(19) -0.11170(14) 0.65418(10) 0.0199(4) Uani 1 1 d . . . . .
O12B O 0.80733(18) 0.17867(15) 0.88981(9) 0.0180(4) Uani 1 1 d . . . . .
O20B O 0.04343(19) 0.90618(15) 0.88362(10) 0.0211(4) Uani 1 1 d . . . . .
N1B N 0.3733(2) 0.50563(17) 0.73769(11) 0.0142(4) Uani 1 1 d . . . . .
N3B N 0.5227(2) 0.38838(17) 0.65481(11) 0.0151(4) Uani 1 1 d . . . . .
N11B N 0.6001(2) 0.25368(17) 0.81871(11) 0.0144(4) Uani 1 1 d . . . . .
N13B N 0.5978(2) 0.32186(17) 0.93026(11) 0.0162(5) Uani 1 1 d . . . . .
C2B C 0.4735(3) 0.5018(2) 0.67370(13) 0.0156(5) Uani 1 1 d . . . . .
C4B C 0.4326(3) 0.3179(2) 0.69352(13) 0.0144(5) Uani 1 1 d . . . . .
H4B H 0.354757 0.322897 0.659210 0.017 Uiso 1 1 calc R U . . .
C5B C 0.5224(3) 0.1889(2) 0.71448(13) 0.0147(5) Uani 1 1 d . . . . .
C6B C 0.5157(3) 0.0994(2) 0.67396(13) 0.0148(5) Uani 1 1 d . . . . .
H6B H 0.447152 0.117464 0.635587 0.018 Uiso 1 1 calc R U . . .
C7B C 0.6092(3) -0.0162(2) 0.68970(13) 0.0154(5) Uani 1 1 d . . . . .
C8B C 0.7137(3) -0.0415(2) 0.74377(14) 0.0174(5) Uani 1 1 d . . . . .
H8B H 0.782076 -0.119505 0.751826 0.021 Uiso 1 1 calc R U . . .
C9B C 0.7185(3) 0.0457(2) 0.78555(14) 0.0168(5) Uani 1 1 d . . . . .
H9B H 0.789384 0.027740 0.822641 0.020 Uiso 1 1 calc R U . . .
C10B C 0.6186(3) 0.1610(2) 0.77324(13) 0.0150(5) Uani 1 1 d . . . . .
C12B C 0.6823(3) 0.2439(2) 0.88164(13) 0.0138(5) Uani 1 1 d . . . . .
C14B C 0.4662(3) 0.4004(2) 0.89548(13) 0.0149(5) Uani 1 1 d . . . . .
H14C H 0.479243 0.475462 0.869063 0.018 Uiso 1 1 calc R U . . .
H14D H 0.382766 0.419206 0.934561 0.018 Uiso 1 1 calc R U . . .
C15B C 0.4468(3) 0.3246(2) 0.83762(13) 0.0140(5) Uani 1 1 d . . . . .
H15B H 0.396886 0.268932 0.866223 0.017 Uiso 1 1 calc R U . . .
C16B C 0.3643(3) 0.3865(2) 0.76414(13) 0.0137(5) Uani 1 1 d . . . . .
H16B H 0.259861 0.391173 0.773783 0.016 Uiso 1 1 calc R U . . .
C17B C 0.2869(3) 0.6077(2) 0.77295(13) 0.0148(5) Uani 1 1 d . . . . .
C18B C 0.1828(3) 0.5980(2) 0.83351(14) 0.0164(5) Uani 1 1 d . . . . .
H18B H 0.168752 0.523025 0.849105 0.020 Uiso 1 1 calc R U . . .
C19B C 0.1000(3) 0.6952(2) 0.87096(14) 0.0164(5) Uani 1 1 d . . . . .
H19B H 0.031367 0.685814 0.912303 0.020 Uiso 1 1 calc R U . . .
C20B C 0.1164(3) 0.8056(2) 0.84881(14) 0.0147(5) Uani 1 1 d . . . . .
C21B C 0.2161(3) 0.8175(2) 0.78703(14) 0.0174(5) Uani 1 1 d . . . . .
H21B H 0.225910 0.893563 0.769932 0.021 Uiso 1 1 calc R U . . .
C22B C 0.3011(3) 0.7201(2) 0.75027(14) 0.0161(5) Uani 1 1 d . . . . .
H22B H 0.369832 0.729981 0.709089 0.019 Uiso 1 1 calc R U . . .
C23B C 0.5972(3) 0.3626(2) 0.57936(14) 0.0225(6) Uani 1 1 d . . . . .
H23D H 0.528110 0.357827 0.544320 0.034 Uiso 1 1 calc R U . . .
H23E H 0.676441 0.286350 0.585351 0.034 Uiso 1 1 calc R U . . .
H23F H 0.637111 0.426185 0.557560 0.034 Uiso 1 1 calc R U . . .
C24B C 0.6584(3) 0.3533(2) 0.99264(14) 0.0211(6) Uani 1 1 d . . . . .
H24D H 0.749753 0.290377 1.005843 0.032 Uiso 1 1 calc R U . . .
H24E H 0.589260 0.361896 1.038337 0.032 Uiso 1 1 calc R U . . .
H24F H 0.677209 0.428759 0.976004 0.032 Uiso 1 1 calc R U . . .
C25B C 0.4857(3) -0.0976(2) 0.61358(14) 0.0213(6) Uani 1 1 d . . . . .
H25D H 0.480697 -0.038217 0.567896 0.032 Uiso 1 1 calc R U . . .
H25E H 0.397649 -0.070832 0.647967 0.032 Uiso 1 1 calc R U . . .
H25F H 0.493057 -0.174051 0.596954 0.032 Uiso 1 1 calc R U . . .
C26B C -0.0544(3) 0.8943(2) 0.94979(14) 0.0219(6) Uani 1 1 d . . . . .
H26D H -0.129586 0.866288 0.934521 0.033 Uiso 1 1 calc R U . . .
H26E H -0.100416 0.971889 0.969186 0.033 Uiso 1 1 calc R U . . .
H26F H -0.000103 0.836758 0.990780 0.033 Uiso 1 1 calc R U . . .


_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
O2A C2A 1.231(3) . ?
O7A C7A 1.372(3) . ?
O7A C25A 1.434(3) . ?
O12A C12A 1.224(3) . ?
O20A C20A 1.376(3) . ?
O20A C26A 1.428(3) . ?
N1A C2A 1.384(3) . ?
N1A C16A 1.466(3) . ?
N1A C17A 1.422(3) . ?
N3A C2A 1.360(3) . ?
N3A C4A 1.465(3) . ?
N3A C23A 1.455(3) . ?
N11A C10A 1.406(3) . ?
N11A C12A 1.395(3) . ?
N11A C15A 1.477(3) . ?
N13A C12A 1.349(3) . ?
N13A C14A 1.458(3) . ?
N13A C24A 1.448(3) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.511(3) . ?
C4A C16A 1.549(3) . ?
C5A C6A 1.382(3) . ?
C5A C10A 1.404(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.396(3) . ?
C7A C8A 1.390(3) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.391(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.391(3) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C14A C15A 1.529(3) . ?
C15A H15A 1.0000 . ?
C15A C16A 1.549(3) . ?
C16A H16A 1.0000 . ?
C17A C18A 1.388(3) . ?
C17A C22A 1.407(3) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.394(3) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.385(3) . ?
C20A C21A 1.386(3) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.383(3) . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
O2B C2B 1.229(3) . ?
O7B C7B 1.378(3) . ?
O7B C25B 1.424(3) . ?
O12B C12B 1.220(3) . ?
O20B C20B 1.370(3) . ?
O20B C26B 1.437(3) . ?
N1B C2B 1.397(3) . ?
N1B C16B 1.463(3) . ?
N1B C17B 1.416(3) . ?
N3B C2B 1.359(3) . ?
N3B C4B 1.465(3) . ?
N3B C23B 1.454(3) . ?
N11B C10B 1.411(3) . ?
N11B C12B 1.399(3) . ?
N11B C15B 1.481(3) . ?
N13B C12B 1.355(3) . ?
N13B C14B 1.448(3) . ?
N13B C24B 1.446(3) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.512(3) . ?
C4B C16B 1.546(3) . ?
C5B C6B 1.393(3) . ?
C5B C10B 1.395(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.386(3) . ?
C7B C8B 1.394(3) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.377(3) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.401(3) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C14B C15B 1.520(3) . ?
C15B H15B 1.0000 . ?
C15B C16B 1.545(3) . ?
C16B H16B 1.0000 . ?
C17B C18B 1.404(3) . ?
C17B C22B 1.396(3) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.384(3) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.380(3) . ?
C20B C21B 1.395(3) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.384(3) . ?
C22B H22B 0.9500 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 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
C7A O7A C25A 117.1(2) . . ?
C20A O20A C26A 117.53(19) . . ?
C2A N1A C16A 110.79(18) . . ?
C2A N1A C17A 126.32(19) . . ?
C17A N1A C16A 122.87(19) . . ?
C2A N3A C4A 111.24(19) . . ?
C2A N3A C23A 120.21(19) . . ?
C23A N3A C4A 120.51(19) . . ?
C10A N11A C15A 117.09(19) . . ?
C12A N11A C10A 125.6(2) . . ?
C12A N11A C15A 110.05(19) . . ?
C12A N13A C14A 111.96(19) . . ?
C12A N13A C24A 121.7(2) . . ?
C24A N13A C14A 121.3(2) . . ?
O2A C2A N1A 126.7(2) . . ?
O2A C2A N3A 124.9(2) . . ?
N3A C2A N1A 108.31(19) . . ?
N3A C4A H4A 109.6 . . ?
N3A C4A C5A 109.85(19) . . ?
N3A C4A C16A 101.44(17) . . ?
C5A C4A H4A 109.6 . . ?
C5A C4A C16A 116.40(19) . . ?
C16A C4A H4A 109.6 . . ?
C6A C5A C4A 121.1(2) . . ?
C6A C5A C10A 119.9(2) . . ?
C10A C5A C4A 118.7(2) . . ?
C5A C6A H6A 119.8 . . ?
C5A C6A C7A 120.5(2) . . ?
C7A C6A H6A 119.8 . . ?
O7A C7A C6A 115.8(2) . . ?
O7A C7A C8A 124.9(2) . . ?
C8A C7A C6A 119.3(2) . . ?
C7A C8A H8A 119.6 . . ?
C7A C8A C9A 120.8(2) . . ?
C9A C8A H8A 119.6 . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A C8A 119.6(2) . . ?
C10A C9A H9A 120.2 . . ?
C5A C10A N11A 115.1(2) . . ?
C9A C10A N11A 125.0(2) . . ?
C9A C10A C5A 119.9(2) . . ?
O12A C12A N11A 125.2(2) . . ?
O12A C12A N13A 127.1(2) . . ?
N13A C12A N11A 107.7(2) . . ?
N13A C14A H14A 111.3 . . ?
N13A C14A H14B 111.3 . . ?
N13A C14A C15A 102.22(18) . . ?
H14A C14A H14B 109.2 . . ?
C15A C14A H14A 111.3 . . ?
C15A C14A H14B 111.3 . . ?
N11A C15A C14A 101.37(19) . . ?
N11A C15A H15A 108.0 . . ?
N11A C15A C16A 112.10(19) . . ?
C14A C15A H15A 108.0 . . ?
C14A C15A C16A 118.78(19) . . ?
C16A C15A H15A 108.0 . . ?
N1A C16A C4A 102.33(18) . . ?
N1A C16A C15A 115.12(19) . . ?
N1A C16A H16A 109.3 . . ?
C4A C16A H16A 109.3 . . ?
C15A C16A C4A 111.16(18) . . ?
C15A C16A H16A 109.3 . . ?
C18A C17A N1A 120.8(2) . . ?
C18A C17A C22A 117.8(2) . . ?
C22A C17A N1A 121.5(2) . . ?
C17A C18A H18A 119.3 . . ?
C17A C18A C19A 121.4(2) . . ?
C19A C18A H18A 119.3 . . ?
C18A C19A H19A 119.9 . . ?
C20A C19A C18A 120.3(2) . . ?
C20A C19A H19A 119.9 . . ?
O20A C20A C19A 125.5(2) . . ?
O20A C20A C21A 115.8(2) . . ?
C19A C20A C21A 118.7(2) . . ?
C20A C21A H21A 119.3 . . ?
C22A C21A C20A 121.4(2) . . ?
C22A C21A H21A 119.3 . . ?
C17A C22A H22A 119.8 . . ?
C21A C22A C17A 120.4(2) . . ?
C21A C22A H22A 119.8 . . ?
N3A C23A H23A 109.5 . . ?
N3A C23A H23B 109.5 . . ?
N3A C23A H23C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N13A C24A H24A 109.5 . . ?
N13A C24A H24B 109.5 . . ?
N13A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
O7A C25A H25A 109.5 . . ?
O7A C25A H25B 109.5 . . ?
O7A C25A H25C 109.5 . . ?
H25A C25A H25B 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
O20A C26A H26A 109.5 . . ?
O20A C26A H26B 109.5 . . ?
O20A C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C7B O7B C25B 117.00(18) . . ?
C20B O20B C26B 117.08(19) . . ?
C2B N1B C16B 110.30(18) . . ?
C2B N1B C17B 127.0(2) . . ?
C17B N1B C16B 122.68(19) . . ?
C2B N3B C4B 111.93(19) . . ?
C2B N3B C23B 120.6(2) . . ?
C23B N3B C4B 120.0(2) . . ?
C10B N11B C15B 115.00(18) . . ?
C12B N11B C10B 124.50(19) . . ?
C12B N11B C15B 108.94(18) . . ?
C12B N13B C14B 111.89(18) . . ?
C12B N13B C24B 121.4(2) . . ?
C24B N13B C14B 122.30(19) . . ?
O2B C2B N1B 125.9(2) . . ?
O2B C2B N3B 126.2(2) . . ?
N3B C2B N1B 107.8(2) . . ?
N3B C4B H4B 109.9 . . ?
N3B C4B C5B 111.67(19) . . ?
N3B C4B C16B 100.86(18) . . ?
C5B C4B H4B 109.9 . . ?
C5B C4B C16B 114.39(19) . . ?
C16B C4B H4B 109.9 . . ?
C6B C5B C4B 121.3(2) . . ?
C6B C5B C10B 119.9(2) . . ?
C10B C5B C4B 118.7(2) . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B C5B 119.9(2) . . ?
C7B C6B H6B 120.0 . . ?
O7B C7B C6B 124.7(2) . . ?
O7B C7B C8B 115.4(2) . . ?
C6B C7B C8B 119.9(2) . . ?
C7B C8B H8B 119.8 . . ?
C9B C8B C7B 120.5(2) . . ?
C9B C8B H8B 119.8 . . ?
C8B C9B H9B 120.1 . . ?
C8B C9B C10B 119.8(2) . . ?
C10B C9B H9B 120.1 . . ?
C5B C10B N11B 115.1(2) . . ?
C5B C10B C9B 119.6(2) . . ?
C9B C10B N11B 125.2(2) . . ?
O12B C12B N11B 125.9(2) . . ?
O12B C12B N13B 127.0(2) . . ?
N13B C12B N11B 107.0(2) . . ?
N13B C14B H14C 111.5 . . ?
N13B C14B H14D 111.5 . . ?
N13B C14B C15B 101.29(18) . . ?
H14C C14B H14D 109.3 . . ?
C15B C14B H14C 111.5 . . ?
C15B C14B H14D 111.5 . . ?
N11B C15B C14B 100.99(18) . . ?
N11B C15B H15B 107.8 . . ?
N11B C15B C16B 112.36(18) . . ?
C14B C15B H15B 107.8 . . ?
C14B C15B C16B 119.34(19) . . ?
C16B C15B H15B 107.8 . . ?
N1B C16B C4B 102.89(18) . . ?
N1B C16B C15B 113.98(19) . . ?
N1B C16B H16B 109.6 . . ?
C4B C16B H16B 109.6 . . ?
C15B C16B C4B 110.97(18) . . ?
C15B C16B H16B 109.6 . . ?
C18B C17B N1B 120.0(2) . . ?
C22B C17B N1B 122.6(2) . . ?
C22B C17B C18B 117.5(2) . . ?
C17B C18B H18B 119.3 . . ?
C19B C18B C17B 121.4(2) . . ?
C19B C18B H18B 119.3 . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B C18B 120.6(2) . . ?
C20B C19B H19B 119.7 . . ?
O20B C20B C19B 125.1(2) . . ?
O20B C20B C21B 116.3(2) . . ?
C19B C20B C21B 118.6(2) . . ?
C20B C21B H21B 119.5 . . ?
C22B C21B C20B 121.1(2) . . ?
C22B C21B H21B 119.5 . . ?
C17B C22B H22B 119.6 . . ?
C21B C22B C17B 120.8(2) . . ?
C21B C22B H22B 119.6 . . ?
N3B C23B H23D 109.5 . . ?
N3B C23B H23E 109.5 . . ?
N3B C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
N13B C24B H24D 109.5 . . ?
N13B C24B H24E 109.5 . . ?
N13B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
O7B C25B H25D 109.5 . . ?
O7B C25B H25E 109.5 . . ?
O7B C25B H25F 109.5 . . ?
H25D C25B H25E 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
O20B C26B H26D 109.5 . . ?
O20B C26B H26E 109.5 . . ?
O20B C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

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
O7A C7A C8A C9A 179.3(2) . . . . ?
O20A C20A C21A C22A -178.2(2) . . . . ?
N1A C17A C18A C19A -176.9(2) . . . . ?
N1A C17A C22A C21A 176.9(2) . . . . ?
N3A C4A C5A C6A 97.6(3) . . . . ?
N3A C4A C5A C10A -75.8(3) . . . . ?
N3A C4A C16A N1A -22.5(2) . . . . ?
N3A C4A C16A C15A 100.9(2) . . . . ?
N11A C15A C16A N1A 90.4(2) . . . . ?
N11A C15A C16A C4A -25.4(3) . . . . ?
N13A C14A C15A N11A 24.7(2) . . . . ?
N13A C14A C15A C16A 148.0(2) . . . . ?
C2A N1A C16A C4A 16.2(2) . . . . ?
C2A N1A C16A C15A -104.5(2) . . . . ?
C2A N1A C17A C18A -175.0(2) . . . . ?
C2A N1A C17A C22A 6.2(4) . . . . ?
C2A N3A C4A C5A 147.0(2) . . . . ?
C2A N3A C4A C16A 23.3(2) . . . . ?
C4A N3A C2A O2A 168.5(2) . . . . ?
C4A N3A C2A N1A -14.1(3) . . . . ?
C4A C5A C6A C7A -172.2(2) . . . . ?
C4A C5A C10A N11A -9.4(3) . . . . ?
C4A C5A C10A C9A 171.8(2) . . . . ?
C5A C4A C16A N1A -141.7(2) . . . . ?
C5A C4A C16A C15A -18.3(3) . . . . ?
C5A C6A C7A O7A 179.8(2) . . . . ?
C5A C6A C7A C8A 0.3(4) . . . . ?
C6A C5A C10A N11A 177.1(2) . . . . ?
C6A C5A C10A C9A -1.7(3) . . . . ?
C6A C7A C8A C9A -1.3(4) . . . . ?
C7A C8A C9A C10A 0.7(4) . . . . ?
C8A C9A C10A N11A -178.0(2) . . . . ?
C8A C9A C10A C5A 0.8(3) . . . . ?
C10A N11A C12A O12A -22.0(4) . . . . ?
C10A N11A C12A N13A 158.7(2) . . . . ?
C10A N11A C15A C14A -173.88(19) . . . . ?
C10A N11A C15A C16A 58.4(3) . . . . ?
C10A C5A C6A C7A 1.2(4) . . . . ?
C12A N11A C10A C5A 173.1(2) . . . . ?
C12A N11A C10A C9A -8.1(4) . . . . ?
C12A N11A C15A C14A -22.0(2) . . . . ?
C12A N11A C15A C16A -149.68(19) . . . . ?
C12A N13A C14A C15A -21.4(3) . . . . ?
C14A N13A C12A O12A -171.2(2) . . . . ?
C14A N13A C12A N11A 8.1(3) . . . . ?
C14A C15A C16A N1A -27.4(3) . . . . ?
C14A C15A C16A C4A -143.1(2) . . . . ?
C15A N11A C10A C5A -39.9(3) . . . . ?
C15A N11A C10A C9A 138.9(2) . . . . ?
C15A N11A C12A O12A -171.0(2) . . . . ?
C15A N11A C12A N13A 9.7(3) . . . . ?
C16A N1A C2A O2A 175.0(2) . . . . ?
C16A N1A C2A N3A -2.4(3) . . . . ?
C16A N1A C17A C18A 3.2(3) . . . . ?
C16A N1A C17A C22A -175.6(2) . . . . ?
C16A C4A C5A C6A -147.9(2) . . . . ?
C16A C4A C5A C10A 38.7(3) . . . . ?
C17A N1A C2A O2A -6.6(4) . . . . ?
C17A N1A C2A N3A 176.0(2) . . . . ?
C17A N1A C16A C4A -162.2(2) . . . . ?
C17A N1A C16A C15A 77.1(3) . . . . ?
C17A C18A C19A C20A 0.0(4) . . . . ?
C18A C17A C22A C21A -1.9(3) . . . . ?
C18A C19A C20A O20A 178.2(2) . . . . ?
C18A C19A C20A C21A -1.8(4) . . . . ?
C19A C20A C21A C22A 1.8(4) . . . . ?
C20A C21A C22A C17A 0.0(4) . . . . ?
C22A C17A C18A C19A 1.9(3) . . . . ?
C23A N3A C2A O2A 19.6(4) . . . . ?
C23A N3A C2A N1A -163.0(2) . . . . ?
C23A N3A C4A C5A -64.2(3) . . . . ?
C23A N3A C4A C16A 172.1(2) . . . . ?
C24A N13A C12A O12A -15.8(4) . . . . ?
C24A N13A C12A N11A 163.4(2) . . . . ?
C24A N13A C14A C15A -176.9(2) . . . . ?
C25A O7A C7A C6A 173.3(2) . . . . ?
C25A O7A C7A C8A -7.2(3) . . . . ?
C26A O20A C20A C19A 3.4(3) . . . . ?
C26A O20A C20A C21A -176.5(2) . . . . ?
O7B C7B C8B C9B -176.9(2) . . . . ?
O20B C20B C21B C22B 176.7(2) . . . . ?
N1B C17B C18B C19B 177.8(2) . . . . ?
N1B C17B C22B C21B -179.0(2) . . . . ?
N3B C4B C5B C6B -107.2(2) . . . . ?
N3B C4B C5B C10B 69.7(3) . . . . ?
N3B C4B C16B N1B 23.5(2) . . . . ?
N3B C4B C16B C15B -98.8(2) . . . . ?
N11B C15B C16B N1B -89.8(2) . . . . ?
N11B C15B C16B C4B 25.8(3) . . . . ?
N13B C14B C15B N11B -30.0(2) . . . . ?
N13B C14B C15B C16B -153.6(2) . . . . ?
C2B N1B C16B C4B -17.6(2) . . . . ?
C2B N1B C16B C15B 102.6(2) . . . . ?
C2B N1B C17B C18B 175.1(2) . . . . ?
C2B N1B C17B C22B -5.2(4) . . . . ?
C2B N3B C4B C5B -145.5(2) . . . . ?
C2B N3B C4B C16B -23.6(2) . . . . ?
C4B N3B C2B O2B -169.7(2) . . . . ?
C4B N3B C2B N1B 13.6(3) . . . . ?
C4B C5B C6B C7B 174.0(2) . . . . ?
C4B C5B C10B N11B 12.9(3) . . . . ?
C4B C5B C10B C9B -170.3(2) . . . . ?
C5B C4B C16B N1B 143.5(2) . . . . ?
C5B C4B C16B C15B 21.2(3) . . . . ?
C5B C6B C7B O7B 178.8(2) . . . . ?
C5B C6B C7B C8B -2.6(4) . . . . ?
C6B C5B C10B N11B -170.1(2) . . . . ?
C6B C5B C10B C9B 6.7(3) . . . . ?
C6B C7B C8B C9B 4.4(4) . . . . ?
C7B C8B C9B C10B -0.6(4) . . . . ?
C8B C9B C10B N11B 171.5(2) . . . . ?
C8B C9B C10B C5B -4.9(4) . . . . ?
C10B N11B C12B O12B 28.5(4) . . . . ?
C10B N11B C12B N13B -152.7(2) . . . . ?
C10B N11B C15B C14B 171.68(19) . . . . ?
C10B N11B C15B C16B -60.0(3) . . . . ?
C10B C5B C6B C7B -2.9(4) . . . . ?
C12B N11B C10B C5B 178.4(2) . . . . ?
C12B N11B C10B C9B 1.8(4) . . . . ?
C12B N11B C15B C14B 26.5(2) . . . . ?
C12B N11B C15B C16B 154.81(19) . . . . ?
C12B N13B C14B C15B 25.9(2) . . . . ?
C14B N13B C12B O12B 169.0(2) . . . . ?
C14B N13B C12B N11B -9.8(3) . . . . ?
C14B C15B C16B N1B 28.1(3) . . . . ?
C14B C15B C16B C4B 143.7(2) . . . . ?
C15B N11B C10B C5B 39.4(3) . . . . ?
C15B N11B C10B C9B -137.2(2) . . . . ?
C15B N11B C12B O12B 169.6(2) . . . . ?
C15B N11B C12B N13B -11.6(2) . . . . ?
C16B N1B C2B O2B -173.2(2) . . . . ?
C16B N1B C2B N3B 3.6(3) . . . . ?
C16B N1B C17B C18B -3.1(3) . . . . ?
C16B N1B C17B C22B 176.6(2) . . . . ?
C16B C4B C5B C6B 139.0(2) . . . . ?
C16B C4B C5B C10B -44.1(3) . . . . ?
C17B N1B C2B O2B 8.5(4) . . . . ?
C17B N1B C2B N3B -174.8(2) . . . . ?
C17B N1B C16B C4B 160.8(2) . . . . ?
C17B N1B C16B C15B -79.0(3) . . . . ?
C17B C18B C19B C20B 1.0(4) . . . . ?
C18B C17B C22B C21B 0.7(3) . . . . ?
C18B C19B C20B O20B -177.8(2) . . . . ?
C18B C19B C20B C21B 1.1(4) . . . . ?
C19B C20B C21B C22B -2.3(4) . . . . ?
C20B C21B C22B C17B 1.4(4) . . . . ?
C22B C17B C18B C19B -1.9(4) . . . . ?
C23B N3B C2B O2B -19.9(4) . . . . ?
C23B N3B C2B N1B 163.4(2) . . . . ?
C23B N3B C4B C5B 64.5(3) . . . . ?
C23B N3B C4B C16B -173.6(2) . . . . ?
C24B N13B C12B O12B 12.1(4) . . . . ?
C24B N13B C12B N11B -166.7(2) . . . . ?
C24B N13B C14B C15B -177.4(2) . . . . ?
C25B O7B C7B C6B -16.3(3) . . . . ?
C25B O7B C7B C8B 165.1(2) . . . . ?
C26B O20B C20B C19B 1.9(3) . . . . ?
C26B O20B C20B C21B -177.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_v
_database_code_depnum_ccdc_archive 'CCDC 2161406'
loop_
_audit_author_name
_audit_author_address
'Julia Voronina'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H32 N4 O8'
_chemical_formula_sum            'C26 H32 N4 O8'
_chemical_formula_weight         528.55
_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           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                   10.678(3)
_cell_length_b                   9.987(3)
_cell_length_c                   24.015(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.609(15)
_cell_angle_gamma                90
_cell_volume                     2517.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.7350.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1967
_diffrn_reflns_av_unetI/netI     0.3270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.973
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1343
_reflns_number_total             4418
_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.
;
# start Validation Reply Form
_vrf_RINTA01_v                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Crystals were very poor quality
;
_vrf_PLAT020_v                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.197 Report
RESPONSE: Crystals were very poor quality
;
_vrf_PLAT026_v                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        30% Check 
RESPONSE: Crystals were very poor quality
;
_vrf_PLAT340_v                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01187 Ang.  
RESPONSE: Crystals were very poor quality
;
# end Validation Reply Form
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0065(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2888
_refine_ls_R_factor_gt           0.0968
_refine_ls_restrained_S_all      0.954
_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)+(0.0809P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2804
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C18(H18), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C)
;
_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
O2 O -0.0855(6) 1.4167(6) -0.0611(2) 0.0508(18) Uani 1 1 d . . . . .
O6 O 0.0732(6) 1.2149(6) 0.1445(2) 0.0505(17) Uani 1 1 d . . . . .
O7 O 0.1311(6) 0.9880(6) 0.21265(18) 0.0511(17) Uani 1 1 d . . . . .
O8 O 0.2411(6) 0.7760(6) 0.1738(2) 0.0522(18) Uani 1 1 d . . . . .
O12 O 0.4123(6) 0.8350(6) 0.0005(2) 0.0540(19) Uani 1 1 d . . . . .
O19 O 0.4346(7) 1.5763(6) -0.1374(2) 0.064(2) Uani 1 1 d . . . . .
O20 O 0.2679(6) 1.5889(6) -0.2366(2) 0.0568(18) Uani 1 1 d . . . . .
O21 O 0.0405(6) 1.4742(6) -0.2486(2) 0.0512(17) Uani 1 1 d . . . . .
N1 N 0.1243(7) 1.3450(7) -0.0494(2) 0.044(2) Uani 1 1 d . . . . .
N3 N 0.0046(7) 1.2666(7) 0.0092(2) 0.045(2) Uani 1 1 d . . . . .
N11 N 0.2668(7) 1.0147(7) 0.0000(2) 0.045(2) Uani 1 1 d . . . . .
N13 N 0.3424(7) 0.9707(8) -0.0780(3) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.0049(10) 1.3520(9) -0.0367(3) 0.042(2) Uani 1 1 d . . . . .
C4 C 0.1370(9) 1.2424(9) 0.0376(3) 0.048(3) Uani 1 1 d . . . . .
H4 H 0.1662 1.3189 0.0636 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1602(9) 1.1120(9) 0.0707(3) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.1328(8) 1.1051(10) 0.1257(3) 0.047(2) Uani 1 1 d . . . . .
C7 C 0.1570(8) 0.9905(9) 0.1583(3) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.2177(8) 0.8847(9) 0.1386(3) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.2552(8) 0.8883(8) 0.0864(3) 0.044(2) Uani 1 1 d . . . . .
H9 H 0.2994 0.8153 0.0736 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2255(8) 1.0046(9) 0.0525(3) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.3477(10) 0.9295(10) -0.0229(3) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.2895(9) 1.1030(10) -0.0874(3) 0.061(3) Uani 1 1 d . . . . .
H14A H 0.2371 1.1114 -0.1259 0.073 Uiso 1 1 calc R U . . .
H14B H 0.3573 1.1719 -0.0826 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2062(9) 1.1157(9) -0.0411(3) 0.051(3) Uani 1 1 d . . . . .
H15 H 0.1173 1.0866 -0.0571 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2022(9) 1.2510(9) -0.0138(3) 0.054(3) Uani 1 1 d . . . . .
H16 H 0.2905 1.2871 -0.0023 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1612(10) 1.4047(9) -0.0988(3) 0.050(3) Uani 1 1 d . . . . .
C18 C 0.2789(10) 1.4590(9) -0.0927(3) 0.050(3) Uani 1 1 d . . . . .
H18 H 0.3359 1.4531 -0.0574 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3165(9) 1.5241(8) -0.1388(3) 0.043(2) Uani 1 1 d . . . . .
C20 C 0.2330(9) 1.5275(8) -0.1899(3) 0.044(2) Uani 1 1 d . . . . .
C21 C 0.1148(9) 1.4698(8) -0.1960(3) 0.038(2) Uani 1 1 d . . . . .
C22 C 0.0742(8) 1.4042(7) -0.1503(3) 0.041(2) Uani 1 1 d . . . . .
H22 H -0.0068 1.3623 -0.1543 0.049 Uiso 1 1 calc R U . . .
C23 C -0.0970(8) 1.2834(9) 0.0419(3) 0.052(3) Uani 1 1 d . . . . .
H23A H -0.0736 1.3545 0.0700 0.078 Uiso 1 1 calc R U . . .
H23B H -0.1092 1.1994 0.0613 0.078 Uiso 1 1 calc R U . . .
H23C H -0.1763 1.3077 0.0164 0.078 Uiso 1 1 calc R U . . .
C24 C 0.4359(9) 0.9265(9) -0.1112(3) 0.064(3) Uani 1 1 d . . . . .
H24A H 0.5190 0.9661 -0.0956 0.095 Uiso 1 1 calc R U . . .
H24B H 0.4092 0.9549 -0.1506 0.095 Uiso 1 1 calc R U . . .
H24C H 0.4426 0.8286 -0.1096 0.095 Uiso 1 1 calc R U . . .
C25 C 0.1568(9) 1.2949(9) 0.1864(3) 0.061(3) Uani 1 1 d . . . . .
H25A H 0.2289 1.3275 0.1701 0.092 Uiso 1 1 calc R U . . .
H25B H 0.1886 1.2398 0.2198 0.092 Uiso 1 1 calc R U . . .
H25C H 0.1094 1.3714 0.1975 0.092 Uiso 1 1 calc R U . . .
C26 C -0.0023(9) 0.9749(9) 0.2135(3) 0.054(3) Uani 1 1 d . . . . .
H26A H -0.0386 0.9040 0.1872 0.081 Uiso 1 1 calc R U . . .
H26B H -0.0454 1.0598 0.2020 0.081 Uiso 1 1 calc R U . . .
H26C H -0.0140 0.9520 0.2519 0.081 Uiso 1 1 calc R U . . .
C27 C 0.3205(9) 0.6701(9) 0.1584(3) 0.058(3) Uani 1 1 d . . . . .
H27A H 0.2793 0.6303 0.1223 0.087 Uiso 1 1 calc R U . . .
H27B H 0.3325 0.6011 0.1879 0.087 Uiso 1 1 calc R U . . .
H27C H 0.4035 0.7069 0.1544 0.087 Uiso 1 1 calc R U . . .
C28 C 0.5241(10) 1.5702(10) -0.0856(4) 0.079(4) Uani 1 1 d . . . . .
H28A H 0.6042 1.6122 -0.0907 0.118 Uiso 1 1 calc R U . . .
H28B H 0.5398 1.4764 -0.0745 0.118 Uiso 1 1 calc R U . . .
H28C H 0.4899 1.6177 -0.0560 0.118 Uiso 1 1 calc R U . . .
C29 C 0.2121(10) 1.7176(9) -0.2490(4) 0.072(3) Uani 1 1 d . . . . .
H29A H 0.2378 1.7536 -0.2831 0.108 Uiso 1 1 calc R U . . .
H29B H 0.2410 1.7781 -0.2170 0.108 Uiso 1 1 calc R U . . .
H29C H 0.1191 1.7098 -0.2552 0.108 Uiso 1 1 calc R U . . .
C30 C -0.0695(9) 1.3935(9) -0.2604(3) 0.051(3) Uani 1 1 d . . . . .
H30A H -0.1050 1.3971 -0.3010 0.077 Uiso 1 1 calc R U . . .
H30B H -0.1329 1.4264 -0.2389 0.077 Uiso 1 1 calc R U . . .
H30C H -0.0471 1.3008 -0.2494 0.077 Uiso 1 1 calc R U . . .


_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
O2 C2 1.218(10) . ?
O6 C6 1.385(9) . ?
O6 C25 1.455(9) . ?
O7 C7 1.383(8) . ?
O7 C26 1.434(9) . ?
O8 C8 1.369(8) . ?
O8 C27 1.446(9) . ?
O12 C12 1.241(10) . ?
O19 C19 1.360(9) . ?
O19 C28 1.422(10) . ?
O20 C20 1.390(9) . ?
O20 C29 1.425(9) . ?
O21 C21 1.363(9) . ?
O21 C30 1.410(9) . ?
N1 C2 1.365(10) . ?
N1 C16 1.429(10) . ?
N1 C17 1.445(10) . ?
N3 C2 1.396(9) . ?
N3 C4 1.472(10) . ?
N3 C23 1.461(9) . ?
N11 C10 1.413(8) . ?
N11 C12 1.396(11) . ?
N11 C15 1.475(9) . ?
N13 C12 1.378(9) . ?
N13 C14 1.439(10) . ?
N13 C24 1.456(10) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(10) . ?
C4 C16 1.528(10) . ?
C5 C6 1.407(9) . ?
C5 C10 1.393(11) . ?
C6 C7 1.383(11) . ?
C7 C8 1.369(10) . ?
C8 C9 1.386(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.420(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.553(10) . ?
C15 H15 1.0000 . ?
C15 C16 1.505(10) . ?
C16 H16 1.0000 . ?
C17 C18 1.352(11) . ?
C17 C22 1.404(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.405(10) . ?
C19 C20 1.378(11) . ?
C20 C21 1.370(11) . ?
C21 C22 1.413(10) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C6 O6 C25 113.5(7) . . ?
C7 O7 C26 112.8(6) . . ?
C8 O8 C27 118.1(6) . . ?
C19 O19 C28 118.4(7) . . ?
C20 O20 C29 113.7(6) . . ?
C21 O21 C30 119.2(6) . . ?
C2 N1 C16 111.4(7) . . ?
C2 N1 C17 124.7(7) . . ?
C16 N1 C17 123.0(7) . . ?
C2 N3 C4 108.9(7) . . ?
C2 N3 C23 117.7(7) . . ?
C23 N3 C4 121.0(6) . . ?
C10 N11 C15 118.3(7) . . ?
C12 N11 C10 128.7(7) . . ?
C12 N11 C15 112.4(6) . . ?
C12 N13 C14 111.8(7) . . ?
C12 N13 C24 121.6(8) . . ?
C14 N13 C24 118.8(7) . . ?
O2 C2 N1 127.6(8) . . ?
O2 C2 N3 125.9(9) . . ?
N1 C2 N3 106.5(8) . . ?
N3 C4 H4 109.0 . . ?
N3 C4 C5 115.6(7) . . ?
N3 C4 C16 99.1(6) . . ?
C5 C4 H4 109.0 . . ?
C5 C4 C16 114.5(7) . . ?
C16 C4 H4 109.0 . . ?
C6 C5 C4 119.4(8) . . ?
C10 C5 C4 122.6(7) . . ?
C10 C5 C6 117.4(8) . . ?
O6 C6 C5 117.0(8) . . ?
C7 C6 O6 121.3(7) . . ?
C7 C6 C5 121.5(8) . . ?
O7 C7 C6 120.0(8) . . ?
C8 C7 O7 120.1(8) . . ?
C8 C7 C6 119.6(7) . . ?
O8 C8 C9 121.9(8) . . ?
C7 C8 O8 116.3(7) . . ?
C7 C8 C9 121.8(8) . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(8) . . ?
C10 C9 H9 121.0 . . ?
N11 C10 C9 119.8(7) . . ?
C5 C10 N11 118.8(7) . . ?
C5 C10 C9 121.4(7) . . ?
O12 C12 N11 128.2(7) . . ?
O12 C12 N13 125.7(9) . . ?
N13 C12 N11 106.1(9) . . ?
N13 C14 H14A 111.2 . . ?
N13 C14 H14B 111.2 . . ?
N13 C14 C15 102.8(7) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
N11 C15 C14 100.7(7) . . ?
N11 C15 H15 109.1 . . ?
N11 C15 C16 111.5(6) . . ?
C14 C15 H15 109.1 . . ?
C16 C15 C14 116.8(8) . . ?
C16 C15 H15 109.1 . . ?
N1 C16 C4 102.6(7) . . ?
N1 C16 C15 113.0(7) . . ?
N1 C16 H16 110.1 . . ?
C4 C16 H16 110.1 . . ?
C15 C16 C4 110.8(7) . . ?
C15 C16 H16 110.1 . . ?
C18 C17 N1 117.7(8) . . ?
C18 C17 C22 123.2(8) . . ?
C22 C17 N1 119.1(9) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(8) . . ?
C19 C18 H18 120.2 . . ?
O19 C19 C18 123.8(8) . . ?
O19 C19 C20 117.3(8) . . ?
C20 C19 C18 118.7(9) . . ?
C19 C20 O20 120.3(9) . . ?
C21 C20 O20 118.5(7) . . ?
C21 C20 C19 121.2(8) . . ?
O21 C21 C20 117.0(8) . . ?
O21 C21 C22 121.7(8) . . ?
C20 C21 C22 121.3(7) . . ?
C17 C22 C21 115.8(8) . . ?
C17 C22 H22 122.1 . . ?
C21 C22 H22 122.1 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N13 C24 H24A 109.5 . . ?
N13 C24 H24B 109.5 . . ?
N13 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C27 H27A 109.5 . . ?
O8 C27 H27B 109.5 . . ?
O8 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O19 C28 H28A 109.5 . . ?
O19 C28 H28B 109.5 . . ?
O19 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O20 C29 H29A 109.5 . . ?
O20 C29 H29B 109.5 . . ?
O20 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O21 C30 H30A 109.5 . . ?
O21 C30 H30B 109.5 . . ?
O21 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O6 C6 C7 O7 -5.3(12) . . . . ?
O6 C6 C7 C8 -179.1(8) . . . . ?
O7 C7 C8 O8 4.8(12) . . . . ?
O7 C7 C8 C9 -174.3(7) . . . . ?
O8 C8 C9 C10 179.2(7) . . . . ?
O19 C19 C20 O20 -3.5(12) . . . . ?
O19 C19 C20 C21 176.0(7) . . . . ?
O20 C20 C21 O21 1.6(11) . . . . ?
O20 C20 C21 C22 179.1(7) . . . . ?
O21 C21 C22 C17 178.6(8) . . . . ?
N1 C17 C18 C19 -176.7(7) . . . . ?
N1 C17 C22 C21 177.1(7) . . . . ?
N3 C4 C5 C6 -81.4(10) . . . . ?
N3 C4 C5 C10 108.6(9) . . . . ?
N3 C4 C16 N1 31.3(8) . . . . ?
N3 C4 C16 C15 -89.5(8) . . . . ?
N11 C15 C16 N1 -169.3(7) . . . . ?
N11 C15 C16 C4 -54.9(10) . . . . ?
N13 C14 C15 N11 22.4(8) . . . . ?
N13 C14 C15 C16 143.3(8) . . . . ?
C2 N1 C16 C4 -22.4(9) . . . . ?
C2 N1 C16 C15 96.9(8) . . . . ?
C2 N1 C17 C18 142.6(9) . . . . ?
C2 N1 C17 C22 -37.2(12) . . . . ?
C2 N3 C4 C5 -154.8(7) . . . . ?
C2 N3 C4 C16 -31.9(8) . . . . ?
C4 N3 C2 O2 -161.9(8) . . . . ?
C4 N3 C2 N1 19.8(8) . . . . ?
C4 C5 C6 O6 6.6(12) . . . . ?
C4 C5 C6 C7 -177.4(8) . . . . ?
C4 C5 C10 N11 -2.9(13) . . . . ?
C4 C5 C10 C9 174.6(8) . . . . ?
C5 C4 C16 N1 155.0(7) . . . . ?
C5 C4 C16 C15 34.2(11) . . . . ?
C5 C6 C7 O7 178.8(8) . . . . ?
C5 C6 C7 C8 5.1(13) . . . . ?
C6 C5 C10 N11 -173.1(7) . . . . ?
C6 C5 C10 C9 4.5(13) . . . . ?
C6 C7 C8 O8 178.5(7) . . . . ?
C6 C7 C8 C9 -0.5(13) . . . . ?
C7 C8 C9 C10 -1.8(12) . . . . ?
C8 C9 C10 N11 177.2(7) . . . . ?
C8 C9 C10 C5 -0.3(12) . . . . ?
C10 N11 C12 O12 -9.0(15) . . . . ?
C10 N11 C12 N13 170.8(7) . . . . ?
C10 N11 C15 C14 173.7(7) . . . . ?
C10 N11 C15 C16 49.1(10) . . . . ?
C10 C5 C6 O6 177.1(7) . . . . ?
C10 C5 C6 C7 -6.9(13) . . . . ?
C12 N11 C10 C5 170.3(8) . . . . ?
C12 N11 C10 C9 -7.3(12) . . . . ?
C12 N11 C15 C14 -14.3(9) . . . . ?
C12 N11 C15 C16 -138.9(8) . . . . ?
C12 N13 C14 C15 -25.2(9) . . . . ?
C14 N13 C12 O12 -163.5(9) . . . . ?
C14 N13 C12 N11 16.7(10) . . . . ?
C14 C15 C16 N1 75.7(10) . . . . ?
C14 C15 C16 C4 -169.9(7) . . . . ?
C15 N11 C10 C5 -19.2(11) . . . . ?
C15 N11 C10 C9 163.2(7) . . . . ?
C15 N11 C12 O12 180.0(9) . . . . ?
C15 N11 C12 N13 -0.2(10) . . . . ?
C16 N1 C2 O2 -175.7(8) . . . . ?
C16 N1 C2 N3 2.6(9) . . . . ?
C16 N1 C17 C18 -49.5(12) . . . . ?
C16 N1 C17 C22 130.7(9) . . . . ?
C16 C4 C5 C6 164.2(8) . . . . ?
C16 C4 C5 C10 -5.7(12) . . . . ?
C17 N1 C2 O2 -6.6(14) . . . . ?
C17 N1 C2 N3 171.7(7) . . . . ?
C17 N1 C16 C4 168.3(7) . . . . ?
C17 N1 C16 C15 -72.4(11) . . . . ?
C17 C18 C19 O19 -176.9(8) . . . . ?
C17 C18 C19 C20 -1.9(13) . . . . ?
C18 C17 C22 C21 -2.7(13) . . . . ?
C18 C19 C20 O20 -178.8(7) . . . . ?
C18 C19 C20 C21 0.6(13) . . . . ?
C19 C20 C21 O21 -177.8(8) . . . . ?
C19 C20 C21 C22 -0.4(13) . . . . ?
C20 C21 C22 C17 1.3(12) . . . . ?
C22 C17 C18 C19 3.0(14) . . . . ?
C23 N3 C2 O2 -19.2(12) . . . . ?
C23 N3 C2 N1 162.5(7) . . . . ?
C23 N3 C4 C5 64.0(9) . . . . ?
C23 N3 C4 C16 -173.1(7) . . . . ?
C24 N13 C12 O12 -14.8(14) . . . . ?
C24 N13 C12 N11 165.4(7) . . . . ?
C24 N13 C14 C15 -174.9(7) . . . . ?
C25 O6 C6 C5 -106.6(8) . . . . ?
C25 O6 C6 C7 77.4(10) . . . . ?
C26 O7 C7 C6 76.1(10) . . . . ?
C26 O7 C7 C8 -110.2(9) . . . . ?
C27 O8 C8 C7 -171.4(8) . . . . ?
C27 O8 C8 C9 7.6(11) . . . . ?
C28 O19 C19 C18 -2.9(12) . . . . ?
C28 O19 C19 C20 -178.0(8) . . . . ?
C29 O20 C20 C19 -103.3(10) . . . . ?
C29 O20 C20 C21 77.3(10) . . . . ?
C30 O21 C21 C20 166.8(8) . . . . ?
C30 O21 C21 C22 -10.6(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dp9_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2164571'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of
Russia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(3aS,3bR,11bS)-9-chloro-3-(3-chlorophenyl)-1,5-dimethyl-1,3a,3b,4,5,11b-hexahydro-2H-diimidazo[1,5-a:4',5'-c]quinoline-2,6(3H)-dione
_chemical_name_common            ?
_chemical_formula_moiety         '0.333(C20 H18 Cl2 N4 O2)'
_chemical_formula_sum            'C6.67 H6 Cl0.67 N1.33 O0.67'
_chemical_formula_weight         139.09
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100.00
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'
Cl Cl 0.1484 0.1585 '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'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8202(9)
_cell_length_b                   12.3589(10)
_cell_length_c                   15.5997(14)
_cell_angle_alpha                92.661(3)
_cell_angle_beta                 109.964(3)
_cell_angle_gamma                107.892(3)
_cell_volume                     1839.0(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1794 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.9082.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.156
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            34578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.058
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5302
_reflns_number_total             8012
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         8012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.070
_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)+(0.0432P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C2B(H2B), C3A(H3A), C2A(H2A), C11A(H11A), C3B(H3B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C20B(H20B), C18B(H18B), C10A(H10A), C10B(H10B), C20A(H20A), C17B(H17B),
 C6A(H6A), C6B(H6B), C18A(H18A), C7B(H7B), C8B(H8B), C7A(H7A), C17A(H17A),
 C8A(H8A)
2.d Idealised Me refined as rotating group:
 C4B(H4BA,H4BB,H4BC), C14B(H14D,H14E,H14F), C14A(H14A,H14B,H14C), C4A(H4AA,
 H4AB,H4AC)
;
_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
Cl1A Cl 0.65965(7) 0.02949(5) 0.19080(4) 0.03268(17) Uani 1 1 d . . . . .
Cl2B Cl 0.42529(6) 0.59572(5) 0.33279(4) 0.03229(16) Uani 1 1 d . . . . .
Cl2A Cl 1.10331(7) 0.89680(5) -0.08881(4) 0.03625(17) Uani 1 1 d . . . . .
Cl1B Cl -0.29160(7) 1.01977(6) 0.69917(5) 0.04197(19) Uani 1 1 d . . . . .
O1B O 0.11779(17) 1.05527(13) 0.62257(11) 0.0281(4) Uani 1 1 d . . . . .
O2B O -0.05746(17) 0.45950(13) 0.34823(11) 0.0263(4) Uani 1 1 d . . . . .
O2A O 0.88603(17) 0.47373(13) -0.15328(11) 0.0272(4) Uani 1 1 d . . . . .
O1A O 0.51106(18) 0.51888(14) 0.17579(11) 0.0312(4) Uani 1 1 d . . . . .
N4A N 0.8266(2) 0.51197(15) -0.02678(12) 0.0210(4) Uani 1 1 d . . . . .
N2B N 0.0223(2) 0.85391(15) 0.59588(13) 0.0216(4) Uani 1 1 d . . . . .
N3A N 0.7293(2) 0.33694(15) -0.10959(13) 0.0226(4) Uani 1 1 d . . . . .
N1B N 0.2124(2) 0.93951(15) 0.56432(13) 0.0230(4) Uani 1 1 d . . . . .
N4B N 0.01944(19) 0.65570(15) 0.40625(13) 0.0225(4) Uani 1 1 d . . . . .
N2A N 0.6691(2) 0.44106(16) 0.15066(13) 0.0224(4) Uani 1 1 d . . . . .
N3B N -0.1948(2) 0.54642(15) 0.38911(13) 0.0253(5) Uani 1 1 d . . . . .
N1A N 0.7034(2) 0.62810(16) 0.14604(13) 0.0253(5) Uani 1 1 d . . . . .
C13B C -0.0768(2) 0.54377(19) 0.37827(15) 0.0199(5) Uani 1 1 d . . . . .
C16B C 0.2575(2) 0.76764(18) 0.50564(15) 0.0206(5) Uani 1 1 d . . . . .
C15B C 0.1649(2) 0.68414(19) 0.42854(16) 0.0213(5) Uani 1 1 d . . . . .
C1B C 0.1175(2) 0.96011(19) 0.59726(15) 0.0215(5) Uani 1 1 d . . . . .
C2B C 0.0537(2) 0.76162(19) 0.55452(16) 0.0218(5) Uani 1 1 d . . . . .
H2B H 0.038295 0.692271 0.585415 0.026 Uiso 1 1 calc R U . . .
C5B C -0.0796(2) 0.83722(19) 0.63603(15) 0.0212(5) Uani 1 1 d . . . . .
C3A C 0.8323(2) 0.61286(19) 0.14544(16) 0.0227(5) Uani 1 1 d . . . . .
H3A H 0.903688 0.634810 0.210046 0.027 Uiso 1 1 calc R U . . .
C5A C 0.5875(2) 0.32190(19) 0.13538(15) 0.0221(5) Uani 1 1 d . . . . .
C2A C 0.7828(2) 0.48164(19) 0.11615(15) 0.0210(5) Uani 1 1 d . . . . .
H2A H 0.859353 0.450339 0.145466 0.025 Uiso 1 1 calc R U . . .
C16A C 0.8940(2) 0.68301(19) 0.08294(15) 0.0225(5) Uani 1 1 d . . . . .
C11A C 0.7244(2) 0.45024(19) 0.01106(15) 0.0225(5) Uani 1 1 d . . . . .
H11A H 0.638633 0.471726 -0.014818 0.027 Uiso 1 1 calc R U . . .
C15A C 0.8924(2) 0.63150(19) 0.00004(15) 0.0216(5) Uani 1 1 d . . . . .
C20B C 0.2161(2) 0.63040(19) 0.37410(16) 0.0224(5) Uani 1 1 d . . . . .
H20B H 0.153780 0.575132 0.320325 0.027 Uiso 1 1 calc R U . . .
C3B C 0.2079(2) 0.82091(18) 0.57106(16) 0.0215(5) Uani 1 1 d . . . . .
H3B H 0.265504 0.818259 0.635982 0.026 Uiso 1 1 calc R U . . .
C18B C 0.4533(3) 0.73946(19) 0.47771(16) 0.0247(5) Uani 1 1 d . . . . .
H18B H 0.551316 0.756935 0.495054 0.030 Uiso 1 1 calc R U . . .
C10A C 0.6552(3) 0.24466(19) 0.16854(15) 0.0238(5) Uani 1 1 d . . . . .
H10A H 0.753039 0.271139 0.203710 0.029 Uiso 1 1 calc R U . . .
C10B C -0.1334(2) 0.9245(2) 0.64504(16) 0.0245(5) Uani 1 1 d . . . . .
H10B H -0.104869 0.994078 0.622174 0.029 Uiso 1 1 calc R U . . .
C12A C 0.6898(3) 0.32450(19) -0.02971(16) 0.0245(5) Uani 1 1 d . . . . .
H12A H 0.745244 0.286478 0.014672 0.029 Uiso 1 1 calc R U . . .
H12B H 0.588854 0.279902 -0.048127 0.029 Uiso 1 1 calc R U . . .
C11B C -0.0315(2) 0.7317(2) 0.45008(16) 0.0231(5) Uani 1 1 d . . . . .
H11B H -0.022815 0.803786 0.422523 0.028 Uiso 1 1 calc R U . . .
C20A C 0.9560(2) 0.6990(2) -0.05287(16) 0.0242(5) Uani 1 1 d . . . . .
H20A H 0.955236 0.664626 -0.108895 0.029 Uiso 1 1 calc R U . . .
C13A C 0.8199(2) 0.4433(2) -0.10302(16) 0.0231(5) Uani 1 1 d . . . . .
C9A C 0.5765(3) 0.1280(2) 0.14906(16) 0.0247(5) Uani 1 1 d . . . . .
C1A C 0.6165(3) 0.5286(2) 0.15939(16) 0.0262(6) Uani 1 1 d . . . . .
C17B C 0.4004(2) 0.79333(19) 0.52925(17) 0.0250(5) Uani 1 1 d . . . . .
H17B H 0.463734 0.849461 0.582276 0.030 Uiso 1 1 calc R U . . .
C19B C 0.3590(3) 0.6596(2) 0.40037(16) 0.0246(5) Uani 1 1 d . . . . .
C6A C 0.4439(3) 0.2823(2) 0.08580(16) 0.0276(6) Uani 1 1 d . . . . .
H6A H 0.397686 0.335442 0.064274 0.033 Uiso 1 1 calc R U . . .
C12B C -0.1864(2) 0.65953(19) 0.42372(17) 0.0262(6) Uani 1 1 d . . . . .
H12C H -0.213438 0.658461 0.478299 0.031 Uiso 1 1 calc R U . . .
H12D H -0.247348 0.689764 0.375463 0.031 Uiso 1 1 calc R U . . .
C9B C -0.2286(3) 0.9079(2) 0.68772(16) 0.0280(6) Uani 1 1 d . . . . .
C6B C -0.1264(2) 0.7349(2) 0.66792(16) 0.0262(6) Uani 1 1 d . . . . .
H6B H -0.090863 0.674830 0.661733 0.031 Uiso 1 1 calc R U . . .
C18A C 1.0241(3) 0.8698(2) 0.05823(17) 0.0297(6) Uani 1 1 d . . . . .
H18A H 1.068292 0.950867 0.077413 0.036 Uiso 1 1 calc R U . . .
C4B C 0.3413(3) 1.03179(19) 0.57871(18) 0.0290(6) Uani 1 1 d . . . . .
H4BA H 0.325557 1.105711 0.579612 0.044 Uiso 1 1 calc R U . . .
H4BB H 0.373172 1.020105 0.528381 0.044 Uiso 1 1 calc R U . . .
H4BC H 0.412862 1.032229 0.637894 0.044 Uiso 1 1 calc R U . . .
C14B C -0.3177(2) 0.44545(19) 0.37057(16) 0.0260(6) Uani 1 1 d . . . . .
H14D H -0.301496 0.377234 0.348891 0.039 Uiso 1 1 calc R U . . .
H14E H -0.398282 0.455357 0.322877 0.039 Uiso 1 1 calc R U . . .
H14F H -0.336447 0.435388 0.427400 0.039 Uiso 1 1 calc R U . . .
C7B C -0.2244(3) 0.7206(2) 0.70859(17) 0.0314(6) Uani 1 1 d . . . . .
H7B H -0.256949 0.649943 0.729090 0.038 Uiso 1 1 calc R U . . .
C19A C 1.0198(3) 0.8160(2) -0.02257(16) 0.0269(6) Uani 1 1 d . . . . .
C8B C -0.2759(3) 0.8077(2) 0.71984(17) 0.0325(6) Uani 1 1 d . . . . .
H8B H -0.341780 0.798514 0.748876 0.039 Uiso 1 1 calc R U . . .
C7A C 0.3682(3) 0.1654(2) 0.06774(17) 0.0327(6) Uani 1 1 d . . . . .
H7A H 0.270014 0.138759 0.033799 0.039 Uiso 1 1 calc R U . . .
C17A C 0.9620(3) 0.8019(2) 0.11056(17) 0.0277(6) Uani 1 1 d . . . . .
H17A H 0.965796 0.837384 0.167175 0.033 Uiso 1 1 calc R U . . .
C8A C 0.4340(3) 0.0871(2) 0.09857(16) 0.0307(6) Uani 1 1 d . . . . .
H8A H 0.382243 0.006769 0.085343 0.037 Uiso 1 1 calc R U . . .
C14A C 0.7057(3) 0.23866(19) -0.17400(17) 0.0300(6) Uani 1 1 d . . . . .
H14A H 0.755474 0.263619 -0.215560 0.045 Uiso 1 1 calc R U . . .
H14B H 0.605177 0.202805 -0.210350 0.045 Uiso 1 1 calc R U . . .
H14C H 0.740371 0.182606 -0.139952 0.045 Uiso 1 1 calc R U . . .
C4A C 0.7015(3) 0.7391(2) 0.17969(17) 0.0342(7) Uani 1 1 d . . . . .
H4AA H 0.615574 0.727723 0.191699 0.051 Uiso 1 1 calc R U . . .
H4AB H 0.704615 0.789145 0.132987 0.051 Uiso 1 1 calc R U . . .
H4AC H 0.783041 0.775206 0.237071 0.051 Uiso 1 1 calc R U . . .


_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
Cl1A C9A 1.750(2) . ?
Cl2B C19B 1.742(2) . ?
Cl2A C19A 1.750(2) . ?
Cl1B C9B 1.746(2) . ?
O1B C1B 1.222(3) . ?
O2B C13B 1.226(2) . ?
O2A C13A 1.230(3) . ?
O1A C1A 1.225(3) . ?
N4A C11A 1.457(3) . ?
N4A C15A 1.399(3) . ?
N4A C13A 1.397(3) . ?
N2B C1B 1.391(3) . ?
N2B C2B 1.467(3) . ?
N2B C5B 1.413(3) . ?
N3A C12A 1.450(3) . ?
N3A C13A 1.351(3) . ?
N3A C14A 1.439(3) . ?
N1B C1B 1.376(3) . ?
N1B C3B 1.461(3) . ?
N1B C4B 1.443(3) . ?
N4B C13B 1.392(3) . ?
N4B C15B 1.413(3) . ?
N4B C11B 1.472(3) . ?
N2A C5A 1.425(3) . ?
N2A C2A 1.468(3) . ?
N2A C1A 1.388(3) . ?
N3B C13B 1.353(3) . ?
N3B C12B 1.440(3) . ?
N3B C14B 1.447(3) . ?
N1A C3A 1.467(3) . ?
N1A C1A 1.374(3) . ?
N1A C4A 1.455(3) . ?
C16B C15B 1.394(3) . ?
C16B C3B 1.514(3) . ?
C16B C17B 1.388(3) . ?
C15B C20B 1.402(3) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.525(3) . ?
C2B C11B 1.533(3) . ?
C5B C10B 1.396(3) . ?
C5B C6B 1.393(3) . ?
C3A H3A 1.0000 . ?
C3A C2A 1.535(3) . ?
C3A C16A 1.522(3) . ?
C5A C10A 1.390(3) . ?
C5A C6A 1.389(3) . ?
C2A H2A 1.0000 . ?
C2A C11A 1.523(3) . ?
C16A C15A 1.407(3) . ?
C16A C17A 1.395(3) . ?
C11A H11A 1.0000 . ?
C11A C12A 1.532(3) . ?
C15A C20A 1.396(3) . ?
C20B H20B 0.9500 . ?
C20B C19B 1.378(3) . ?
C3B H3B 1.0000 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.384(3) . ?
C18B C19B 1.379(3) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.387(3) . ?
C10B H10B 0.9500 . ?
C10B C9B 1.378(3) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C11B H11B 1.0000 . ?
C11B C12B 1.533(3) . ?
C20A H20A 0.9500 . ?
C20A C19A 1.375(3) . ?
C9A C8A 1.382(3) . ?
C17B H17B 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C7A 1.384(3) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C9B C8B 1.374(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.383(3) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.377(3) . ?
C18A C17A 1.383(3) . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B H4BC 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C7B H7B 0.9500 . ?
C7B C8B 1.385(3) . ?
C8B H8B 0.9500 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.381(3) . ?
C17A H17A 0.9500 . ?
C8A H8A 0.9500 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 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
C15A N4A C11A 119.71(18) . . ?
C13A N4A C11A 111.12(18) . . ?
C13A N4A C15A 127.4(2) . . ?
C1B N2B C2B 109.26(18) . . ?
C1B N2B C5B 125.21(18) . . ?
C5B N2B C2B 125.27(18) . . ?
C13A N3A C12A 112.58(18) . . ?
C13A N3A C14A 123.3(2) . . ?
C14A N3A C12A 121.91(19) . . ?
C1B N1B C3B 108.80(18) . . ?
C1B N1B C4B 119.32(19) . . ?
C4B N1B C3B 121.71(18) . . ?
C13B N4B C15B 124.30(19) . . ?
C13B N4B C11B 110.96(18) . . ?
C15B N4B C11B 119.42(18) . . ?
C5A N2A C2A 121.63(18) . . ?
C1A N2A C5A 122.8(2) . . ?
C1A N2A C2A 109.77(18) . . ?
C13B N3B C12B 113.81(19) . . ?
C13B N3B C14B 123.92(18) . . ?
C12B N3B C14B 122.24(19) . . ?
C1A N1A C3A 110.62(18) . . ?
C1A N1A C4A 119.5(2) . . ?
C4A N1A C3A 121.9(2) . . ?
O2B C13B N4B 125.7(2) . . ?
O2B C13B N3B 127.0(2) . . ?
N3B C13B N4B 107.29(18) . . ?
C15B C16B C3B 122.1(2) . . ?
C17B C16B C15B 119.0(2) . . ?
C17B C16B C3B 118.5(2) . . ?
C16B C15B N4B 118.8(2) . . ?
C16B C15B C20B 120.2(2) . . ?
C20B C15B N4B 121.0(2) . . ?
O1B C1B N2B 126.8(2) . . ?
O1B C1B N1B 125.5(2) . . ?
N1B C1B N2B 107.75(18) . . ?
N2B C2B H2B 112.0 . . ?
N2B C2B C3B 101.48(17) . . ?
N2B C2B C11B 109.90(18) . . ?
C3B C2B H2B 112.0 . . ?
C3B C2B C11B 109.04(19) . . ?
C11B C2B H2B 112.0 . . ?
C10B C5B N2B 119.9(2) . . ?
C6B C5B N2B 120.79(19) . . ?
C6B C5B C10B 119.3(2) . . ?
N1A C3A H3A 109.0 . . ?
N1A C3A C2A 101.19(18) . . ?
N1A C3A C16A 113.84(18) . . ?
C2A C3A H3A 109.0 . . ?
C16A C3A H3A 109.0 . . ?
C16A C3A C2A 114.61(18) . . ?
C10A C5A N2A 118.6(2) . . ?
C6A C5A N2A 121.1(2) . . ?
C6A C5A C10A 120.2(2) . . ?
N2A C2A C3A 101.99(17) . . ?
N2A C2A H2A 111.5 . . ?
N2A C2A C11A 109.76(18) . . ?
C3A C2A H2A 111.5 . . ?
C11A C2A C3A 110.22(18) . . ?
C11A C2A H2A 111.5 . . ?
C15A C16A C3A 122.3(2) . . ?
C17A C16A C3A 119.4(2) . . ?
C17A C16A C15A 118.1(2) . . ?
N4A C11A C2A 110.91(18) . . ?
N4A C11A H11A 108.9 . . ?
N4A C11A C12A 102.00(18) . . ?
C2A C11A H11A 108.9 . . ?
C2A C11A C12A 117.00(19) . . ?
C12A C11A H11A 108.9 . . ?
N4A C15A C16A 118.1(2) . . ?
C20A C15A N4A 121.6(2) . . ?
C20A C15A C16A 120.2(2) . . ?
C15B C20B H20B 120.8 . . ?
C19B C20B C15B 118.5(2) . . ?
C19B C20B H20B 120.8 . . ?
N1B C3B C16B 115.73(19) . . ?
N1B C3B C2B 100.56(17) . . ?
N1B C3B H3B 108.7 . . ?
C16B C3B C2B 114.13(19) . . ?
C16B C3B H3B 108.7 . . ?
C2B C3B H3B 108.7 . . ?
C17B C18B H18B 121.1 . . ?
C19B C18B H18B 121.1 . . ?
C19B C18B C17B 117.8(2) . . ?
C5A C10A H10A 120.8 . . ?
C9A C10A C5A 118.4(2) . . ?
C9A C10A H10A 120.8 . . ?
C5B C10B H10B 120.6 . . ?
C9B C10B C5B 118.8(2) . . ?
C9B C10B H10B 120.6 . . ?
N3A C12A C11A 102.05(18) . . ?
N3A C12A H12A 111.4 . . ?
N3A C12A H12B 111.4 . . ?
C11A C12A H12A 111.4 . . ?
C11A C12A H12B 111.4 . . ?
H12A C12A H12B 109.2 . . ?
N4B C11B C2B 109.67(18) . . ?
N4B C11B H11B 110.0 . . ?
N4B C11B C12B 102.75(17) . . ?
C2B C11B H11B 110.0 . . ?
C2B C11B C12B 114.2(2) . . ?
C12B C11B H11B 110.0 . . ?
C15A C20A H20A 120.5 . . ?
C19A C20A C15A 118.9(2) . . ?
C19A C20A H20A 120.5 . . ?
O2A C13A N4A 126.3(2) . . ?
O2A C13A N3A 126.8(2) . . ?
N3A C13A N4A 106.8(2) . . ?
C10A C9A Cl1A 119.11(19) . . ?
C8A C9A Cl1A 118.86(18) . . ?
C8A C9A C10A 122.0(2) . . ?
O1A C1A N2A 126.1(2) . . ?
O1A C1A N1A 125.9(2) . . ?
N1A C1A N2A 108.0(2) . . ?
C16B C17B H17B 119.1 . . ?
C18B C17B C16B 121.8(2) . . ?
C18B C17B H17B 119.1 . . ?
C20B C19B Cl2B 119.33(18) . . ?
C20B C19B C18B 122.7(2) . . ?
C18B C19B Cl2B 117.95(18) . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A C5A 120.0(2) . . ?
C7A C6A H6A 120.0 . . ?
N3B C12B C11B 103.23(17) . . ?
N3B C12B H12C 111.1 . . ?
N3B C12B H12D 111.1 . . ?
C11B C12B H12C 111.1 . . ?
C11B C12B H12D 111.1 . . ?
H12C C12B H12D 109.1 . . ?
C10B C9B Cl1B 117.44(19) . . ?
C8B C9B Cl1B 119.7(2) . . ?
C8B C9B C10B 122.8(2) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B C5B 120.2(2) . . ?
C7B C6B H6B 119.9 . . ?
C19A C18A H18A 121.1 . . ?
C19A C18A C17A 117.8(2) . . ?
C17A C18A H18A 121.1 . . ?
N1B C4B H4BA 109.5 . . ?
N1B C4B H4BB 109.5 . . ?
N1B C4B H4BC 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
N3B C14B H14D 109.5 . . ?
N3B C14B H14E 109.5 . . ?
N3B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C6B C7B H7B 119.5 . . ?
C6B C7B C8B 121.0(2) . . ?
C8B C7B H7B 119.5 . . ?
C20A C19A Cl2A 117.52(19) . . ?
C20A C19A C18A 122.7(2) . . ?
C18A C19A Cl2A 119.70(19) . . ?
C9B C8B C7B 118.0(2) . . ?
C9B C8B H8B 121.0 . . ?
C7B C8B H8B 121.0 . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A C6A 120.7(2) . . ?
C8A C7A H7A 119.7 . . ?
C16A C17A H17A 118.9 . . ?
C18A C17A C16A 122.2(2) . . ?
C18A C17A H17A 118.9 . . ?
C9A C8A H8A 120.7 . . ?
C7A C8A C9A 118.7(2) . . ?
C7A C8A H8A 120.7 . . ?
N3A C14A H14A 109.5 . . ?
N3A C14A H14B 109.5 . . ?
N3A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
N1A C4A H4AA 109.5 . . ?
N1A C4A H4AB 109.5 . . ?
N1A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?

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
Cl1A C9A C8A C7A 178.40(19) . . . . ?
Cl1B C9B C8B C7B 179.35(19) . . . . ?
N4A C11A C12A N3A -22.2(2) . . . . ?
N4A C15A C20A C19A -179.6(2) . . . . ?
N2B C2B C3B N1B -32.6(2) . . . . ?
N2B C2B C3B C16B -157.15(18) . . . . ?
N2B C2B C11B N4B 169.25(18) . . . . ?
N2B C2B C11B C12B -76.0(2) . . . . ?
N2B C5B C10B C9B -177.5(2) . . . . ?
N2B C5B C6B C7B 178.8(2) . . . . ?
N4B C15B C20B C19B -178.5(2) . . . . ?
N4B C11B C12B N3B 12.9(2) . . . . ?
N2A C5A C10A C9A -176.5(2) . . . . ?
N2A C5A C6A C7A 176.6(2) . . . . ?
N2A C2A C11A N4A 166.59(17) . . . . ?
N2A C2A C11A C12A -77.0(2) . . . . ?
N1A C3A C2A N2A -27.9(2) . . . . ?
N1A C3A C2A C11A 88.6(2) . . . . ?
N1A C3A C16A C15A -109.7(2) . . . . ?
N1A C3A C16A C17A 74.1(3) . . . . ?
C13B N4B C15B C16B -137.7(2) . . . . ?
C13B N4B C15B C20B 42.8(3) . . . . ?
C13B N4B C11B C2B 108.2(2) . . . . ?
C13B N4B C11B C12B -13.6(2) . . . . ?
C13B N3B C12B C11B -9.0(3) . . . . ?
C16B C15B C20B C19B 2.0(3) . . . . ?
C15B N4B C13B O2B -18.4(4) . . . . ?
C15B N4B C13B N3B 162.6(2) . . . . ?
C15B N4B C11B C2B -47.1(3) . . . . ?
C15B N4B C11B C12B -168.99(19) . . . . ?
C15B C16B C3B N1B -106.4(2) . . . . ?
C15B C16B C3B C2B 9.7(3) . . . . ?
C15B C16B C17B C18B 0.9(3) . . . . ?
C15B C20B C19B Cl2B -178.97(17) . . . . ?
C15B C20B C19B C18B -0.1(4) . . . . ?
C1B N2B C2B C3B 23.4(2) . . . . ?
C1B N2B C2B C11B -91.9(2) . . . . ?
C1B N2B C5B C10B 27.8(3) . . . . ?
C1B N2B C5B C6B -151.4(2) . . . . ?
C1B N1B C3B C16B 156.3(2) . . . . ?
C1B N1B C3B C2B 32.8(2) . . . . ?
C2B N2B C1B O1B 176.0(2) . . . . ?
C2B N2B C1B N1B -3.7(2) . . . . ?
C2B N2B C5B C10B -158.7(2) . . . . ?
C2B N2B C5B C6B 22.1(3) . . . . ?
C2B C11B C12B N3B -105.8(2) . . . . ?
C5B N2B C1B O1B -9.6(4) . . . . ?
C5B N2B C1B N1B 170.73(19) . . . . ?
C5B N2B C2B C3B -151.0(2) . . . . ?
C5B N2B C2B C11B 93.7(3) . . . . ?
C5B C10B C9B Cl1B 179.11(17) . . . . ?
C5B C10B C9B C8B -1.7(4) . . . . ?
C5B C6B C7B C8B -1.2(4) . . . . ?
C3A N1A C1A O1A 169.3(2) . . . . ?
C3A N1A C1A N2A -10.9(2) . . . . ?
C3A C2A C11A N4A 55.0(2) . . . . ?
C3A C2A C11A C12A 171.41(19) . . . . ?
C3A C16A C15A N4A 2.6(3) . . . . ?
C3A C16A C15A C20A -177.1(2) . . . . ?
C3A C16A C17A C18A 177.9(2) . . . . ?
C5A N2A C2A C3A 177.53(19) . . . . ?
C5A N2A C2A C11A 60.7(3) . . . . ?
C5A N2A C1A O1A 17.3(4) . . . . ?
C5A N2A C1A N1A -162.49(19) . . . . ?
C5A C10A C9A Cl1A -179.61(17) . . . . ?
C5A C10A C9A C8A -0.4(3) . . . . ?
C5A C6A C7A C8A 0.0(4) . . . . ?
C2A N2A C5A C10A 58.9(3) . . . . ?
C2A N2A C5A C6A -118.9(2) . . . . ?
C2A N2A C1A O1A 170.8(2) . . . . ?
C2A N2A C1A N1A -9.0(2) . . . . ?
C2A C3A C16A C15A 6.1(3) . . . . ?
C2A C3A C16A C17A -170.1(2) . . . . ?
C2A C11A C12A N3A -143.4(2) . . . . ?
C16A C3A C2A N2A -150.83(18) . . . . ?
C16A C3A C2A C11A -34.3(3) . . . . ?
C16A C15A C20A C19A 0.0(3) . . . . ?
C11A N4A C15A C16A 20.4(3) . . . . ?
C11A N4A C15A C20A -160.0(2) . . . . ?
C11A N4A C13A O2A 174.7(2) . . . . ?
C11A N4A C13A N3A -6.5(2) . . . . ?
C15A N4A C11A C2A -50.2(3) . . . . ?
C15A N4A C11A C12A -175.55(19) . . . . ?
C15A N4A C13A O2A 10.0(4) . . . . ?
C15A N4A C13A N3A -171.1(2) . . . . ?
C15A C16A C17A C18A 1.5(4) . . . . ?
C15A C20A C19A Cl2A 177.92(17) . . . . ?
C15A C20A C19A C18A 0.2(4) . . . . ?
C3B N1B C1B O1B 161.0(2) . . . . ?
C3B N1B C1B N2B -19.3(2) . . . . ?
C3B C16B C15B N4B 5.7(3) . . . . ?
C3B C16B C15B C20B -174.8(2) . . . . ?
C3B C16B C17B C18B 173.6(2) . . . . ?
C3B C2B C11B N4B 58.8(2) . . . . ?
C3B C2B C11B C12B 173.54(17) . . . . ?
C10A C5A C6A C7A -1.2(3) . . . . ?
C10A C9A C8A C7A -0.8(4) . . . . ?
C10B C5B C6B C7B -0.4(3) . . . . ?
C10B C9B C8B C7B 0.2(4) . . . . ?
C12A N3A C13A O2A 169.1(2) . . . . ?
C12A N3A C13A N4A -9.8(3) . . . . ?
C11B N4B C13B O2B -172.3(2) . . . . ?
C11B N4B C13B N3B 8.6(2) . . . . ?
C11B N4B C15B C16B 14.2(3) . . . . ?
C11B N4B C15B C20B -165.3(2) . . . . ?
C11B C2B C3B N1B 83.4(2) . . . . ?
C11B C2B C3B C16B -41.2(2) . . . . ?
C13A N4A C11A C2A 143.74(19) . . . . ?
C13A N4A C11A C12A 18.4(2) . . . . ?
C13A N4A C15A C16A -176.1(2) . . . . ?
C13A N4A C15A C20A 3.5(3) . . . . ?
C13A N3A C12A C11A 20.7(3) . . . . ?
C1A N2A C5A C10A -150.6(2) . . . . ?
C1A N2A C5A C6A 31.5(3) . . . . ?
C1A N2A C2A C3A 23.7(2) . . . . ?
C1A N2A C2A C11A -93.2(2) . . . . ?
C1A N1A C3A C2A 24.8(2) . . . . ?
C1A N1A C3A C16A 148.23(19) . . . . ?
C17B C16B C15B N4B 178.1(2) . . . . ?
C17B C16B C15B C20B -2.3(3) . . . . ?
C17B C16B C3B N1B 81.1(3) . . . . ?
C17B C16B C3B C2B -162.9(2) . . . . ?
C17B C18B C19B Cl2B 177.55(17) . . . . ?
C17B C18B C19B C20B -1.3(4) . . . . ?
C19B C18B C17B C16B 0.9(3) . . . . ?
C6A C5A C10A C9A 1.4(3) . . . . ?
C6A C7A C8A C9A 1.0(4) . . . . ?
C12B N3B C13B O2B -178.3(2) . . . . ?
C12B N3B C13B N4B 0.7(3) . . . . ?
C6B C5B C10B C9B 1.8(3) . . . . ?
C6B C7B C8B C9B 1.3(4) . . . . ?
C4B N1B C1B O1B 15.1(3) . . . . ?
C4B N1B C1B N2B -165.17(19) . . . . ?
C4B N1B C3B C16B -58.8(3) . . . . ?
C4B N1B C3B C2B 177.7(2) . . . . ?
C14B N3B C13B O2B 3.4(4) . . . . ?
C14B N3B C13B N4B -177.6(2) . . . . ?
C14B N3B C12B C11B 169.3(2) . . . . ?
C19A C18A C17A C16A -1.3(4) . . . . ?
C17A C16A C15A N4A 178.8(2) . . . . ?
C17A C16A C15A C20A -0.8(3) . . . . ?
C17A C18A C19A Cl2A -177.22(18) . . . . ?
C17A C18A C19A C20A 0.4(4) . . . . ?
C14A N3A C12A C11A -175.6(2) . . . . ?
C14A N3A C13A O2A 5.5(4) . . . . ?
C14A N3A C13A N4A -173.3(2) . . . . ?
C4A N1A C3A C2A 173.30(19) . . . . ?
C4A N1A C3A C16A -63.2(3) . . . . ?
C4A N1A C1A O1A 20.0(4) . . . . ?
C4A N1A C1A N2A -160.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_a_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2161405'
loop_
_audit_author_name
_audit_author_address
'Julia Voronina'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Cl2 N4 O2'
_chemical_formula_sum            'C20 H18 Cl2 N4 O2'
_chemical_formula_weight         417.28
_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'
Cl Cl 0.1484 0.1585 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8126(4)
_cell_length_b                   23.7747(9)
_cell_length_c                   9.4899(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.6060(10)
_cell_angle_gamma                90
_cell_volume                     1861.09(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8911
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0600 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9012.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19811
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4271
_reflns_number_total             4938
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.077
_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)+(0.0363P)²+1.0183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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
Cl1 Cl 0.31902(6) 0.03267(2) 0.86129(5) 0.03257(11) Uani 1 1 d . . . . .
Cl2 Cl 0.14240(5) 0.58786(2) 0.86655(5) 0.03203(11) Uani 1 1 d . . . . .
O2 O -0.01995(13) 0.34041(5) 0.49931(12) 0.0225(2) Uani 1 1 d . . . . .
O12 O 0.69822(13) 0.26030(5) 0.66471(13) 0.0258(2) Uani 1 1 d . . . . .
N1 N 0.16754(14) 0.34394(5) 0.74349(13) 0.0176(2) Uani 1 1 d . . . . .
N3 N 0.10420(14) 0.26067(5) 0.62938(13) 0.0176(2) Uani 1 1 d . . . . .
N11 N 0.49352(15) 0.26629(5) 0.76690(14) 0.0185(2) Uani 1 1 d . . . . .
N13 N 0.64675(15) 0.34131(5) 0.77465(15) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.07308(16) 0.31753(6) 0.61136(15) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.19350(17) 0.24701(6) 0.78837(15) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.114960 0.236386 0.838440 0.021 Uiso 1 1 calc R U . . .
C5 C 0.31130(17) 0.19947(6) 0.80374(15) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.26957(18) 0.14497(6) 0.83011(16) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.171754 0.138043 0.848056 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3728(2) 0.10095(6) 0.82980(17) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.5164(2) 0.11014(7) 0.80468(18) 0.0263(3) Uani 1 1 d . . . . .
H8 H 0.583978 0.079292 0.802274 0.032 Uiso 1 1 calc R U . . .
C9 C 0.56168(19) 0.16466(6) 0.78295(17) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.661476 0.171343 0.768493 0.028 Uiso 1 1 calc R U . . .
C10 C 0.45885(17) 0.20944(6) 0.78262(16) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.62215(17) 0.28667(6) 0.72826(16) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.51334(18) 0.36170(6) 0.81794(18) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.428158 0.379749 0.732170 0.027 Uiso 1 1 calc R U . . .
H14B H 0.551652 0.388649 0.902679 0.027 Uiso 1 1 calc R U . . .
C15 C 0.45254(17) 0.30716(6) 0.86506(16) 0.0182(3) Uani 1 1 d . . . . .
H15 H 0.521304 0.298869 0.971794 0.022 Uiso 1 1 calc R U . . .
C16 C 0.27318(16) 0.30418(6) 0.85146(15) 0.0169(3) Uani 1 1 d . . . . .
H16 H 0.265065 0.310659 0.952688 0.020 Uiso 1 1 calc R U . . .
C17 C 0.16348(16) 0.40225(6) 0.77261(16) 0.0173(3) Uani 1 1 d . . . . .
C18 C 0.1850(2) 0.42102(7) 0.91728(17) 0.0247(3) Uani 1 1 d . . . . .
H18 H 0.203616 0.394566 0.996630 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1796(2) 0.47814(7) 0.94677(18) 0.0286(3) Uani 1 1 d . . . . .
H19 H 0.193827 0.490738 1.045609 0.034 Uiso 1 1 calc R U . . .
C20 C 0.15333(18) 0.51633(6) 0.83118(17) 0.0219(3) Uani 1 1 d . . . . .
C21 C 0.13498(19) 0.49868(7) 0.68749(18) 0.0251(3) Uani 1 1 d . . . . .
H21 H 0.118663 0.525414 0.609116 0.030 Uiso 1 1 calc R U . . .
C22 C 0.14051(19) 0.44174(6) 0.65821(17) 0.0232(3) Uani 1 1 d . . . . .
H22 H 0.128572 0.429520 0.559560 0.028 Uiso 1 1 calc R U . . .
C23 C -0.02010(17) 0.22140(6) 0.54059(17) 0.0212(3) Uani 1 1 d . . . . .
H23A H -0.093349 0.212543 0.594865 0.032 Uiso 1 1 calc R U . . .
H23B H 0.031560 0.186777 0.523962 0.032 Uiso 1 1 calc R U . . .
H23C H -0.081932 0.238533 0.443355 0.032 Uiso 1 1 calc R U . . .
C24 C 0.7341(2) 0.37978(7) 0.7116(2) 0.0278(3) Uani 1 1 d . . . . .
H24A H 0.798298 0.358223 0.664439 0.042 Uiso 1 1 calc R U . . .
H24B H 0.806371 0.403396 0.791901 0.042 Uiso 1 1 calc R U . . .
H24C H 0.656595 0.403656 0.635766 0.042 Uiso 1 1 calc R U . . .


_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
Cl1 C7 1.7462(16) . ?
Cl2 C20 1.7426(15) . ?
O2 C2 1.2187(17) . ?
O12 C12 1.2210(18) . ?
N1 C2 1.3874(18) . ?
N1 C16 1.4625(17) . ?
N1 C17 1.4164(18) . ?
N3 C2 1.3781(18) . ?
N3 C4 1.4716(18) . ?
N3 C23 1.4600(18) . ?
N11 C10 1.4052(19) . ?
N11 C12 1.3953(19) . ?
N11 C15 1.4762(17) . ?
N13 C12 1.3642(19) . ?
N13 C14 1.4581(18) . ?
N13 C24 1.453(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.5067(19) . ?
C4 C16 1.550(2) . ?
C5 C6 1.393(2) . ?
C5 C10 1.404(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 C8 1.385(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.529(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.5416(19) . ?
C16 H16 1.0000 . ?
C17 C18 1.392(2) . ?
C17 C22 1.395(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(2) . ?
C20 C21 1.381(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C2 N1 C16 111.85(11) . . ?
C2 N1 C17 124.82(12) . . ?
C17 N1 C16 123.33(11) . . ?
C2 N3 C4 110.79(11) . . ?
C2 N3 C23 118.65(12) . . ?
C23 N3 C4 118.20(12) . . ?
C10 N11 C15 117.10(12) . . ?
C12 N11 C10 126.08(12) . . ?
C12 N11 C15 109.82(12) . . ?
C12 N13 C14 110.81(12) . . ?
C12 N13 C24 120.89(13) . . ?
C24 N13 C14 120.23(13) . . ?
O2 C2 N1 126.30(13) . . ?
O2 C2 N3 126.12(13) . . ?
N3 C2 N1 107.58(11) . . ?
N3 C4 H4 109.5 . . ?
N3 C4 C5 111.49(11) . . ?
N3 C4 C16 102.04(11) . . ?
C5 C4 H4 109.5 . . ?
C5 C4 C16 114.67(12) . . ?
C16 C4 H4 109.5 . . ?
C6 C5 C4 119.90(13) . . ?
C6 C5 C10 119.93(13) . . ?
C10 C5 C4 120.06(13) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.09(14) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 Cl1 118.88(13) . . ?
C8 C7 Cl1 119.72(12) . . ?
C8 C7 C6 121.40(15) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.93(14) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.35(14) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 N11 115.12(12) . . ?
C9 C10 N11 124.62(14) . . ?
C9 C10 C5 120.24(14) . . ?
O12 C12 N11 126.13(14) . . ?
O12 C12 N13 126.57(14) . . ?
N13 C12 N11 107.30(12) . . ?
N13 C14 H14A 111.5 . . ?
N13 C14 H14B 111.5 . . ?
N13 C14 C15 101.58(11) . . ?
H14A C14 H14B 109.3 . . ?
C15 C14 H14A 111.5 . . ?
C15 C14 H14B 111.5 . . ?
N11 C15 C14 100.66(11) . . ?
N11 C15 H15 108.3 . . ?
N11 C15 C16 112.84(11) . . ?
C14 C15 H15 108.3 . . ?
C14 C15 C16 117.98(12) . . ?
C16 C15 H15 108.3 . . ?
N1 C16 C4 101.89(11) . . ?
N1 C16 C15 114.21(12) . . ?
N1 C16 H16 109.3 . . ?
C4 C16 H16 109.3 . . ?
C15 C16 C4 112.61(11) . . ?
C15 C16 H16 109.3 . . ?
C18 C17 N1 120.15(13) . . ?
C18 C17 C22 118.95(13) . . ?
C22 C17 N1 120.90(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.61(14) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.39(15) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 Cl2 119.63(12) . . ?
C19 C20 C21 120.93(14) . . ?
C21 C20 Cl2 119.45(12) . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.64(14) . . ?
C22 C21 H21 120.2 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.46(14) . . ?
C21 C22 H22 119.8 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N13 C24 H24A 109.5 . . ?
N13 C24 H24B 109.5 . . ?
N13 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
Cl1 C7 C8 C9 -178.53(12) . . . . ?
Cl2 C20 C21 C22 -178.77(12) . . . . ?
N1 C17 C18 C19 -179.33(14) . . . . ?
N1 C17 C22 C21 179.30(14) . . . . ?
N3 C4 C5 C6 -99.06(15) . . . . ?
N3 C4 C5 C10 77.14(16) . . . . ?
N3 C4 C16 N1 22.71(13) . . . . ?
N3 C4 C16 C15 -100.08(12) . . . . ?
N11 C15 C16 N1 -94.17(14) . . . . ?
N11 C15 C16 C4 21.43(16) . . . . ?
N13 C14 C15 N11 -29.92(13) . . . . ?
N13 C14 C15 C16 -153.11(12) . . . . ?
C2 N1 C16 C4 -16.97(14) . . . . ?
C2 N1 C16 C15 104.73(13) . . . . ?
C2 N1 C17 C18 144.81(15) . . . . ?
C2 N1 C17 C22 -36.2(2) . . . . ?
C2 N3 C4 C5 -145.65(12) . . . . ?
C2 N3 C4 C16 -22.79(14) . . . . ?
C4 N3 C2 O2 -167.30(13) . . . . ?
C4 N3 C2 N1 13.05(15) . . . . ?
C4 C5 C6 C7 173.97(13) . . . . ?
C4 C5 C10 N11 7.86(19) . . . . ?
C4 C5 C10 C9 -174.07(13) . . . . ?
C5 C4 C16 N1 143.39(11) . . . . ?
C5 C4 C16 C15 20.60(16) . . . . ?
C5 C6 C7 Cl1 -179.45(11) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C5 C10 N11 -175.94(13) . . . . ?
C6 C5 C10 C9 2.1(2) . . . . ?
C6 C7 C8 C9 1.7(2) . . . . ?
C7 C8 C9 C10 -1.8(2) . . . . ?
C8 C9 C10 N11 177.77(14) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C10 N11 C12 O12 20.6(2) . . . . ?
C10 N11 C12 N13 -159.42(13) . . . . ?
C10 N11 C15 C14 178.03(12) . . . . ?
C10 N11 C15 C16 -55.30(16) . . . . ?
C10 C5 C6 C7 -2.2(2) . . . . ?
C12 N11 C10 C5 -172.34(13) . . . . ?
C12 N11 C10 C9 9.7(2) . . . . ?
C12 N11 C15 C14 25.43(14) . . . . ?
C12 N11 C15 C16 152.11(12) . . . . ?
C12 N13 C14 C15 26.88(15) . . . . ?
C14 N13 C12 O12 168.47(15) . . . . ?
C14 N13 C12 N11 -11.54(16) . . . . ?
C14 C15 C16 N1 22.65(17) . . . . ?
C14 C15 C16 C4 138.24(13) . . . . ?
C15 N11 C10 C5 40.05(17) . . . . ?
C15 N11 C10 C9 -137.92(14) . . . . ?
C15 N11 C12 O12 170.11(14) . . . . ?
C15 N11 C12 N13 -9.88(15) . . . . ?
C16 N1 C2 O2 -176.23(13) . . . . ?
C16 N1 C2 N3 3.43(15) . . . . ?
C16 N1 C17 C18 -35.0(2) . . . . ?
C16 N1 C17 C22 144.04(14) . . . . ?
C16 C4 C5 C6 145.63(13) . . . . ?
C16 C4 C5 C10 -38.17(18) . . . . ?
C17 N1 C2 O2 4.0(2) . . . . ?
C17 N1 C2 N3 -176.37(12) . . . . ?
C17 N1 C16 C4 162.83(12) . . . . ?
C17 N1 C16 C15 -75.47(16) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C17 C22 C21 -1.7(2) . . . . ?
C18 C19 C20 Cl2 178.74(13) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C17 0.4(2) . . . . ?
C22 C17 C18 C19 1.6(2) . . . . ?
C23 N3 C2 O2 -25.7(2) . . . . ?
C23 N3 C2 N1 154.62(12) . . . . ?
C23 N3 C4 C5 72.59(15) . . . . ?
C23 N3 C4 C16 -164.55(11) . . . . ?
C24 N13 C12 O12 19.7(2) . . . . ?
C24 N13 C12 N11 -160.28(13) . . . . ?
C24 N13 C14 C15 175.85(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_almir2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2164570'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of
Russia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-methyl-4-(3-methyl-2-oxo-1-phenylimidazolidin-4-yl)-3-phenyl-1,3-dihydro-2H-imidazol-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H20 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H24 N4 O4'
_chemical_formula_weight         384.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_chemical_absolute_configuration ad
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'
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100.00
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.
;

_cell_length_a                   12.5996(6)
_cell_length_b                   7.2670(3)
_cell_length_c                   42.5196(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3893.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9113
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.7110.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.194
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            44052
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.916
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7806
_reflns_number_total             8472
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 3311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         8472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.098
_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)+(0.0593P)²+2.8097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1443
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B), O3(H3C,H3D), O6(H6C,H6D)
2.b Ternary CH refined with riding coordinates:
 C11B(H11B), C11A(H11A)
2.c Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D)
2.d Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C17A(H17A), C20A(H20A), C16B(H16B), C20B(H20B), C17B(H17B),
 C6B(H6B), C18B(H18B), C16A(H16A), C19B(H19B), C6A(H6A), C18A(H18A), C19A(H19A),
  C10B(H10B), C10A(H10A), C7A(H7A), C3A(H3A), C9A(H9A), C9B(H9B), C8A(H8A),
 C7B(H7B), C8B(H8B)
2.e Idealised Me refined as rotating group:
 C14B(H14D,H14E,H14F), C4A(H4AA,H4AB,H4AC), C14A(H14A,H14B,H14C), C4B(H4BA,
 H4BB,H4BC)
;
_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
O1A O 0.1523(2) 0.1674(4) 0.43367(6) 0.0249(6) Uani 1 1 d . . . . .
O2B O 0.7103(2) 0.8574(4) 0.66057(7) 0.0242(6) Uani 1 1 d . . . . .
O4 O 0.2489(2) 0.1736(4) 0.52995(8) 0.0313(7) Uani 1 1 d G . . . .
H4A H 0.183880 0.191099 0.536189 0.047 Uiso 1 1 d G U . . .
H4B H 0.289908 0.256607 0.538321 0.047 Uiso 1 1 d G U . . .
O2A O 0.4632(2) -0.3633(4) 0.34129(8) 0.0281(6) Uani 1 1 d . . . . .
O1B O 0.4020(2) 0.3714(4) 0.56085(7) 0.0295(7) Uani 1 1 d . . . . .
O5 O 0.3150(2) 0.2907(5) 0.47151(8) 0.0359(7) Uani 1 1 d G . . . .
H5A H 0.271238 0.244367 0.457801 0.054 Uiso 1 1 d G U . . .
H5B H 0.296460 0.240956 0.489281 0.054 Uiso 1 1 d G U . . .
N4B N 0.5275(2) 0.8695(4) 0.66958(7) 0.0188(6) Uani 1 1 d . . . . .
N2B N 0.4498(2) 0.6173(4) 0.59376(8) 0.0196(6) Uani 1 1 d . . . . .
N3B N 0.5898(2) 0.9234(5) 0.62167(8) 0.0215(7) Uani 1 1 d . . . . .
N1B N 0.3611(3) 0.6821(5) 0.55130(8) 0.0238(7) Uani 1 1 d . . . . .
N4A N 0.2808(2) -0.3593(4) 0.33154(8) 0.0208(7) Uani 1 1 d . . . . .
N2A N 0.2008(2) -0.0909(4) 0.40352(8) 0.0198(6) Uani 1 1 d . . . . .
N1A N 0.1183(3) -0.1381(5) 0.44799(8) 0.0230(7) Uani 1 1 d . . . . .
N3A N 0.3396(3) -0.4186(4) 0.37948(8) 0.0234(7) Uani 1 1 d . . . . .
C3B C 0.3785(3) 0.8458(6) 0.56706(10) 0.0246(8) Uani 1 1 d . . . . .
H3B H 0.355521 0.964161 0.560425 0.030 Uiso 1 1 calc R U . . .
C13B C 0.6185(3) 0.8798(5) 0.65154(9) 0.0202(8) Uani 1 1 d . . . . .
C2B C 0.4333(3) 0.8086(5) 0.59333(9) 0.0203(7) Uani 1 1 d . . . . .
C1B C 0.4047(3) 0.5398(6) 0.56755(9) 0.0221(8) Uani 1 1 d . . . . .
C15A C 0.2774(3) -0.2970(5) 0.30037(9) 0.0223(8) Uani 1 1 d . . . . .
C12A C 0.1852(3) -0.4044(5) 0.34937(9) 0.0214(8) Uani 1 1 d . . . . .
H12A H 0.153544 -0.521225 0.341893 0.026 Uiso 1 1 calc R U . . .
H12B H 0.131678 -0.305232 0.347567 0.026 Uiso 1 1 calc R U . . .
C15B C 0.5186(3) 0.8019(5) 0.70049(9) 0.0180(7) Uani 1 1 d . . . . .
C12B C 0.4335(3) 0.9193(5) 0.65120(9) 0.0192(7) Uani 1 1 d . . . . .
H12C H 0.402311 1.036013 0.658838 0.023 Uiso 1 1 calc R U . . .
H12D H 0.379040 0.821304 0.652313 0.023 Uiso 1 1 calc R U . . .
C11B C 0.4763(3) 0.9407(5) 0.61715(9) 0.0196(7) Uani 1 1 d . . . . .
H11B H 0.460812 1.068709 0.609842 0.023 Uiso 1 1 calc R U . . .
C17A C 0.1743(4) -0.2454(6) 0.25316(11) 0.0339(10) Uani 1 1 d . . . . .
H17A H 0.110016 -0.260540 0.241800 0.041 Uiso 1 1 calc R U . . .
C1A C 0.1563(3) -0.0030(5) 0.42918(8) 0.0199(7) Uani 1 1 d . . . . .
C11A C 0.2251(3) -0.4231(5) 0.38360(10) 0.0233(8) Uani 1 1 d . . . . .
H11A H 0.204507 -0.547258 0.391692 0.028 Uiso 1 1 calc R U . . .
C13A C 0.3715(3) -0.3771(5) 0.34996(9) 0.0208(8) Uani 1 1 d . . . . .
C2A C 0.1871(3) -0.2806(5) 0.40637(9) 0.0219(8) Uani 1 1 d . . . . .
C20A C 0.3635(3) -0.2104(6) 0.28578(10) 0.0254(8) Uani 1 1 d . . . . .
H20A H 0.429372 -0.200694 0.296514 0.030 Uiso 1 1 calc R U . . .
C16B C 0.4213(3) 0.8160(6) 0.71561(10) 0.0250(8) Uani 1 1 d . . . . .
H16B H 0.363952 0.877652 0.705648 0.030 Uiso 1 1 calc R U . . .
C20B C 0.6027(3) 0.7128(6) 0.71539(9) 0.0227(8) Uani 1 1 d . . . . .
H20B H 0.670000 0.704529 0.705391 0.027 Uiso 1 1 calc R U . . .
C5A C 0.2595(3) 0.0073(5) 0.38002(9) 0.0216(8) Uani 1 1 d . . . . .
C17B C 0.4079(3) 0.7401(6) 0.74522(10) 0.0296(10) Uani 1 1 d . . . . .
H17B H 0.341369 0.751495 0.755537 0.036 Uiso 1 1 calc R U . . .
C6B C 0.4635(5) 0.4664(6) 0.64498(10) 0.0359(11) Uani 1 1 d . . . . .
H6B H 0.392239 0.500266 0.649427 0.043 Uiso 1 1 calc R U . . .
C14B C 0.6646(3) 0.9390(6) 0.59633(10) 0.0281(9) Uani 1 1 d . . . . .
H14D H 0.733826 0.892461 0.603199 0.042 Uiso 1 1 calc R U . . .
H14E H 0.671342 1.068355 0.590159 0.042 Uiso 1 1 calc R U . . .
H14F H 0.639640 0.866638 0.578336 0.042 Uiso 1 1 calc R U . . .
C5B C 0.5082(3) 0.5117(6) 0.61654(10) 0.0272(9) Uani 1 1 d . . . . .
C18B C 0.4908(4) 0.6472(6) 0.76014(10) 0.0307(10) Uani 1 1 d . . . . .
H18B H 0.480896 0.592926 0.780250 0.037 Uiso 1 1 calc R U . . .
C16A C 0.1827(3) -0.3159(6) 0.28337(10) 0.0271(9) Uani 1 1 d . . . . .
H16A H 0.123860 -0.377291 0.292604 0.033 Uiso 1 1 calc R U . . .
C19B C 0.5874(4) 0.6360(6) 0.74503(10) 0.0284(9) Uani 1 1 d . . . . .
H19B H 0.644740 0.574620 0.755062 0.034 Uiso 1 1 calc R U . . .
C4A C 0.0629(4) -0.1045(6) 0.47739(10) 0.0305(9) Uani 1 1 d . . . . .
H4AA H 0.110485 -0.041018 0.492057 0.046 Uiso 1 1 calc R U . . .
H4AB H 0.040578 -0.222029 0.486544 0.046 Uiso 1 1 calc R U . . .
H4AC H 0.000408 -0.027743 0.473417 0.046 Uiso 1 1 calc R U . . .
C6A C 0.2101(4) 0.0546(5) 0.35184(10) 0.0304(9) Uani 1 1 d . . . . .
H6A H 0.137632 0.025240 0.348230 0.037 Uiso 1 1 calc R U . . .
C18A C 0.2578(4) -0.1539(6) 0.23942(11) 0.0346(10) Uani 1 1 d . . . . .
H18A H 0.250619 -0.101473 0.219063 0.042 Uiso 1 1 calc R U . . .
C14A C 0.4128(3) -0.4398(7) 0.40541(10) 0.0318(9) Uani 1 1 d . . . . .
H14A H 0.402793 -0.338632 0.420361 0.048 Uiso 1 1 calc R U . . .
H14B H 0.485733 -0.437834 0.397446 0.048 Uiso 1 1 calc R U . . .
H14C H 0.399329 -0.557286 0.415999 0.048 Uiso 1 1 calc R U . . .
C19A C 0.3531(4) -0.1392(6) 0.25588(11) 0.0311(10) Uani 1 1 d . . . . .
H19A H 0.411804 -0.079219 0.246344 0.037 Uiso 1 1 calc R U . . .
C10B C 0.6123(4) 0.4596(6) 0.60919(14) 0.0371(11) Uani 1 1 d . . . . .
H10B H 0.642524 0.487740 0.589294 0.045 Uiso 1 1 calc R U . . .
C10A C 0.3638(3) 0.0529(6) 0.38589(12) 0.0317(10) Uani 1 1 d . . . . .
H10A H 0.396348 0.021710 0.405321 0.038 Uiso 1 1 calc R U . . .
C4B C 0.3003(3) 0.6631(6) 0.52224(9) 0.0288(9) Uani 1 1 d . . . . .
H4BA H 0.228088 0.622202 0.527207 0.043 Uiso 1 1 calc R U . . .
H4BB H 0.334647 0.572288 0.508586 0.043 Uiso 1 1 calc R U . . .
H4BC H 0.297325 0.782122 0.511439 0.043 Uiso 1 1 calc R U . . .
C7A C 0.2692(6) 0.1456(6) 0.32921(12) 0.0460(14) Uani 1 1 d . . . . .
H7A H 0.237079 0.177114 0.309733 0.055 Uiso 1 1 calc R U . . .
C3A C 0.1361(3) -0.3086(6) 0.43410(10) 0.0267(9) Uani 1 1 d . . . . .
H3A H 0.116111 -0.424507 0.442551 0.032 Uiso 1 1 calc R U . . .
C9A C 0.4203(5) 0.1460(7) 0.36262(16) 0.0501(16) Uani 1 1 d . . . . .
H9A H 0.492214 0.178878 0.366291 0.060 Uiso 1 1 calc R U . . .
C9B C 0.6698(5) 0.3659(7) 0.63185(19) 0.060(2) Uani 1 1 d . . . . .
H9B H 0.740932 0.330804 0.627432 0.072 Uiso 1 1 calc R U . . .
C8A C 0.3734(6) 0.1909(6) 0.33443(14) 0.0522(17) Uani 1 1 d . . . . .
H8A H 0.412995 0.253055 0.318656 0.063 Uiso 1 1 calc R U . . .
C7B C 0.5225(6) 0.3714(7) 0.66715(13) 0.0570(19) Uani 1 1 d . . . . .
H7B H 0.491760 0.339811 0.686831 0.068 Uiso 1 1 calc R U . . .
C8B C 0.6266(6) 0.3224(7) 0.66055(18) 0.070(2) Uani 1 1 d . . . . .
H8B H 0.667723 0.259108 0.675822 0.084 Uiso 1 1 calc R U . . .
O3 O 0.0581(3) 0.3438(5) 0.53142(8) 0.0353(7) Uani 1 1 d G . . . .
H3C H 0.041287 0.353991 0.511666 0.053 Uiso 1 1 d G U . . .
H3D H 0.009888 0.271420 0.539238 0.053 Uiso 1 1 d G U . . .
O6 O 0.5065(3) 0.1275(4) 0.46823(8) 0.0325(7) Uani 1 1 d G . . . .
H6C H 0.444843 0.180512 0.466477 0.049 Uiso 1 1 d G U . . .
H6D H 0.549798 0.200106 0.458163 0.049 Uiso 1 1 d G U . . .


_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
O1A C1A 1.254(5) . ?
O2B C13B 1.229(5) . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8706 . ?
O2A C13A 1.217(5) . ?
O1B C1B 1.257(5) . ?
O5 H5A 0.8706 . ?
O5 H5B 0.8697 . ?
N4B C13B 1.381(5) . ?
N4B C15B 1.408(5) . ?
N4B C12B 1.464(5) . ?
N2B C2B 1.406(5) . ?
N2B C1B 1.372(5) . ?
N2B C5B 1.438(5) . ?
N3B C13B 1.358(5) . ?
N3B C11B 1.448(5) . ?
N3B C14B 1.435(5) . ?
N1B C3B 1.383(5) . ?
N1B C1B 1.360(5) . ?
N1B C4B 1.460(5) . ?
N4A C15A 1.401(5) . ?
N4A C12A 1.461(5) . ?
N4A C13A 1.391(5) . ?
N2A C1A 1.383(5) . ?
N2A C2A 1.394(5) . ?
N2A C5A 1.433(5) . ?
N1A C1A 1.353(5) . ?
N1A C4A 1.452(5) . ?
N1A C3A 1.391(6) . ?
N3A C11A 1.454(5) . ?
N3A C13A 1.352(5) . ?
N3A C14A 1.445(5) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.341(6) . ?
C2B C11B 1.497(5) . ?
C15A C20A 1.399(6) . ?
C15A C16A 1.402(6) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C11A 1.546(6) . ?
C15B C16B 1.388(5) . ?
C15B C20B 1.394(5) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C12B C11B 1.553(5) . ?
C11B H11B 1.0000 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.387(6) . ?
C17A C18A 1.374(7) . ?
C11A H11A 1.0000 . ?
C11A C2A 1.497(6) . ?
C2A C3A 1.358(6) . ?
C20A H20A 0.9500 . ?
C20A C19A 1.379(6) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.385(6) . ?
C20B H20B 0.9500 . ?
C20B C19B 1.391(6) . ?
C5A C6A 1.393(6) . ?
C5A C10A 1.378(6) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.396(7) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.374(7) . ?
C6B C7B 1.385(7) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C5B C10B 1.400(6) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.379(7) . ?
C16A H16A 0.9500 . ?
C19B H19B 0.9500 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C6A H6A 0.9500 . ?
C6A C7A 1.385(7) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.394(7) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C19A H19A 0.9500 . ?
C10B H10B 0.9500 . ?
C10B C9B 1.385(8) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.394(7) . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B H4BC 0.9800 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.371(9) . ?
C3A H3A 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C8A 1.376(9) . ?
C9B H9B 0.9500 . ?
C9B C8B 1.374(11) . ?
C8A H8A 0.9500 . ?
C7B H7B 0.9500 . ?
C7B C8B 1.387(11) . ?
C8B H8B 0.9500 . ?
O3 H3C 0.8691 . ?
O3 H3D 0.8695 . ?
O6 H6C 0.8705 . ?
O6 H6D 0.8712 . ?

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
H4A O4 H4B 109.4 . . ?
H5A O5 H5B 104.5 . . ?
C13B N4B C15B 127.1(3) . . ?
C13B N4B C12B 111.2(3) . . ?
C15B N4B C12B 121.4(3) . . ?
C2B N2B C5B 127.7(3) . . ?
C1B N2B C2B 109.5(3) . . ?
C1B N2B C5B 122.7(3) . . ?
C13B N3B C11B 114.0(3) . . ?
C13B N3B C14B 123.1(3) . . ?
C14B N3B C11B 122.8(3) . . ?
C3B N1B C4B 125.0(4) . . ?
C1B N1B C3B 110.1(3) . . ?
C1B N1B C4B 124.8(3) . . ?
C15A N4A C12A 122.5(3) . . ?
C13A N4A C15A 126.0(3) . . ?
C13A N4A C12A 111.4(3) . . ?
C1A N2A C2A 109.7(3) . . ?
C1A N2A C5A 122.0(3) . . ?
C2A N2A C5A 128.1(3) . . ?
C1A N1A C4A 123.8(4) . . ?
C1A N1A C3A 109.8(3) . . ?
C3A N1A C4A 126.4(4) . . ?
C13A N3A C11A 114.3(3) . . ?
C13A N3A C14A 122.8(3) . . ?
C14A N3A C11A 122.6(3) . . ?
N1B C3B H3B 125.9 . . ?
C2B C3B N1B 108.2(4) . . ?
C2B C3B H3B 125.9 . . ?
O2B C13B N4B 126.9(4) . . ?
O2B C13B N3B 125.0(4) . . ?
N3B C13B N4B 108.1(3) . . ?
N2B C2B C11B 124.9(3) . . ?
C3B C2B N2B 106.7(3) . . ?
C3B C2B C11B 128.4(4) . . ?
O1B C1B N2B 126.5(4) . . ?
O1B C1B N1B 127.9(4) . . ?
N1B C1B N2B 105.6(3) . . ?
N4A C15A C16A 118.8(4) . . ?
C20A C15A N4A 122.7(4) . . ?
C20A C15A C16A 118.4(4) . . ?
N4A C12A H12A 111.0 . . ?
N4A C12A H12B 111.0 . . ?
N4A C12A C11A 103.9(3) . . ?
H12A C12A H12B 109.0 . . ?
C11A C12A H12A 111.0 . . ?
C11A C12A H12B 111.0 . . ?
C16B C15B N4B 118.5(3) . . ?
C16B C15B C20B 119.7(4) . . ?
C20B C15B N4B 121.7(3) . . ?
N4B C12B H12C 111.0 . . ?
N4B C12B H12D 111.0 . . ?
N4B C12B C11B 104.0(3) . . ?
H12C C12B H12D 109.0 . . ?
C11B C12B H12C 111.0 . . ?
C11B C12B H12D 111.0 . . ?
N3B C11B C2B 113.0(3) . . ?
N3B C11B C12B 102.2(3) . . ?
N3B C11B H11B 108.4 . . ?
C2B C11B C12B 116.1(3) . . ?
C2B C11B H11B 108.4 . . ?
C12B C11B H11B 108.4 . . ?
C16A C17A H17A 119.5 . . ?
C18A C17A H17A 119.5 . . ?
C18A C17A C16A 121.0(5) . . ?
O1A C1A N2A 126.3(3) . . ?
O1A C1A N1A 127.7(4) . . ?
N1A C1A N2A 105.9(3) . . ?
N3A C11A C12A 102.0(3) . . ?
N3A C11A H11A 108.6 . . ?
N3A C11A C2A 112.3(3) . . ?
C12A C11A H11A 108.6 . . ?
C2A C11A C12A 116.4(3) . . ?
C2A C11A H11A 108.6 . . ?
O2A C13A N4A 127.0(4) . . ?
O2A C13A N3A 125.6(4) . . ?
N3A C13A N4A 107.4(3) . . ?
N2A C2A C11A 126.0(3) . . ?
C3A C2A N2A 106.4(3) . . ?
C3A C2A C11A 127.5(4) . . ?
C15A C20A H20A 119.9 . . ?
C19A C20A C15A 120.2(4) . . ?
C19A C20A H20A 119.9 . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B C15B 119.9(4) . . ?
C17B C16B H16B 120.0 . . ?
C15B C20B H20B 120.3 . . ?
C19B C20B C15B 119.5(4) . . ?
C19B C20B H20B 120.3 . . ?
C6A C5A N2A 119.5(4) . . ?
C10A C5A N2A 119.0(4) . . ?
C10A C5A C6A 121.5(4) . . ?
C16B C17B H17B 119.5 . . ?
C16B C17B C18B 121.0(4) . . ?
C18B C17B H17B 119.5 . . ?
C5B C6B H6B 120.0 . . ?
C5B C6B C7B 119.9(6) . . ?
C7B C6B H6B 120.0 . . ?
N3B C14B H14D 109.5 . . ?
N3B C14B H14E 109.5 . . ?
N3B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C6B C5B N2B 120.7(4) . . ?
C6B C5B C10B 121.0(4) . . ?
C10B C5B N2B 118.2(4) . . ?
C17B C18B H18B 120.7 . . ?
C19B C18B C17B 118.5(4) . . ?
C19B C18B H18B 120.7 . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A C15A 120.4(4) . . ?
C17A C16A H16A 119.8 . . ?
C20B C19B H19B 119.3 . . ?
C18B C19B C20B 121.4(4) . . ?
C18B C19B H19B 119.3 . . ?
N1A C4A H4AA 109.5 . . ?
N1A C4A H4AB 109.5 . . ?
N1A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C5A C6A H6A 120.8 . . ?
C7A C6A C5A 118.4(5) . . ?
C7A C6A H6A 120.8 . . ?
C17A C18A H18A 120.6 . . ?
C17A C18A C19A 118.8(4) . . ?
C19A C18A H18A 120.6 . . ?
N3A C14A H14A 109.5 . . ?
N3A C14A H14B 109.5 . . ?
N3A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C20A C19A C18A 121.1(4) . . ?
C20A C19A H19A 119.5 . . ?
C18A C19A H19A 119.5 . . ?
C5B C10B H10B 121.0 . . ?
C9B C10B C5B 117.9(6) . . ?
C9B C10B H10B 121.0 . . ?
C5A C10A H10A 120.8 . . ?
C5A C10A C9A 118.4(5) . . ?
C9A C10A H10A 120.8 . . ?
N1B C4B H4BA 109.5 . . ?
N1B C4B H4BB 109.5 . . ?
N1B C4B H4BC 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A C6A 121.2(5) . . ?
C8A C7A H7A 119.4 . . ?
N1A C3A H3A 125.9 . . ?
C2A C3A N1A 108.2(4) . . ?
C2A C3A H3A 125.9 . . ?
C10A C9A H9A 119.5 . . ?
C8A C9A C10A 120.9(5) . . ?
C8A C9A H9A 119.5 . . ?
C10B C9B H9B 119.2 . . ?
C8B C9B C10B 121.6(6) . . ?
C8B C9B H9B 119.2 . . ?
C7A C8A C9A 119.7(5) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A H8A 120.2 . . ?
C6B C7B H7B 120.1 . . ?
C6B C7B C8B 119.8(6) . . ?
C8B C7B H7B 120.1 . . ?
C9B C8B C7B 119.7(5) . . ?
C9B C8B H8B 120.1 . . ?
C7B C8B H8B 120.1 . . ?
H3C O3 H3D 104.5 . . ?
H6C O6 H6D 104.4 . . ?

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
N4B C15B C16B C17B 175.8(4) . . . . ?
N4B C15B C20B C19B -175.1(4) . . . . ?
N4B C12B C11B N3B -7.0(4) . . . . ?
N4B C12B C11B C2B 116.5(3) . . . . ?
N2B C2B C11B N3B 52.7(5) . . . . ?
N2B C2B C11B C12B -64.9(5) . . . . ?
N2B C5B C10B C9B 176.9(4) . . . . ?
N1B C3B C2B N2B -0.1(4) . . . . ?
N1B C3B C2B C11B 176.3(4) . . . . ?
N4A C15A C20A C19A -175.0(4) . . . . ?
N4A C15A C16A C17A 175.9(4) . . . . ?
N4A C12A C11A N3A -9.8(4) . . . . ?
N4A C12A C11A C2A 112.8(4) . . . . ?
N2A C2A C3A N1A 0.3(4) . . . . ?
N2A C5A C6A C7A -178.5(4) . . . . ?
N2A C5A C10A C9A 179.0(4) . . . . ?
N3A C11A C2A N2A 59.5(5) . . . . ?
N3A C11A C2A C3A -118.1(5) . . . . ?
C3B N1B C1B O1B 177.9(4) . . . . ?
C3B N1B C1B N2B -0.1(4) . . . . ?
C3B C2B C11B N3B -123.1(4) . . . . ?
C3B C2B C11B C12B 119.3(4) . . . . ?
C13B N4B C15B C16B 175.1(4) . . . . ?
C13B N4B C15B C20B -8.6(6) . . . . ?
C13B N4B C12B C11B 6.6(4) . . . . ?
C13B N3B C11B C2B -120.0(4) . . . . ?
C13B N3B C11B C12B 5.6(4) . . . . ?
C2B N2B C1B O1B -178.0(4) . . . . ?
C2B N2B C1B N1B 0.0(4) . . . . ?
C2B N2B C5B C6B 79.4(5) . . . . ?
C2B N2B C5B C10B -99.4(5) . . . . ?
C1B N2B C2B C3B 0.1(4) . . . . ?
C1B N2B C2B C11B -176.4(3) . . . . ?
C1B N2B C5B C6B -103.6(5) . . . . ?
C1B N2B C5B C10B 77.6(5) . . . . ?
C1B N1B C3B C2B 0.1(5) . . . . ?
C15A N4A C12A C11A -167.8(3) . . . . ?
C15A N4A C13A O2A -9.4(6) . . . . ?
C15A N4A C13A N3A 172.4(3) . . . . ?
C15A C20A C19A C18A -0.9(6) . . . . ?
C12A N4A C15A C20A 163.4(4) . . . . ?
C12A N4A C15A C16A -14.2(5) . . . . ?
C12A N4A C13A O2A 173.8(4) . . . . ?
C12A N4A C13A N3A -4.3(4) . . . . ?
C12A C11A C2A N2A -57.5(5) . . . . ?
C12A C11A C2A C3A 124.9(4) . . . . ?
C15B N4B C13B O2B -11.5(6) . . . . ?
C15B N4B C13B N3B 169.8(3) . . . . ?
C15B N4B C12B C11B -167.0(3) . . . . ?
C15B C16B C17B C18B -0.7(7) . . . . ?
C15B C20B C19B C18B -0.4(6) . . . . ?
C12B N4B C13B O2B 175.3(4) . . . . ?
C12B N4B C13B N3B -3.4(4) . . . . ?
C12B N4B C15B C16B -12.3(5) . . . . ?
C12B N4B C15B C20B 164.0(4) . . . . ?
C11B N3B C13B O2B 179.6(4) . . . . ?
C11B N3B C13B N4B -1.7(4) . . . . ?
C17A C18A C19A C20A -1.7(6) . . . . ?
C1A N2A C2A C11A -179.3(4) . . . . ?
C1A N2A C2A C3A -1.3(4) . . . . ?
C1A N2A C5A C6A -99.5(4) . . . . ?
C1A N2A C5A C10A 80.4(5) . . . . ?
C1A N1A C3A C2A 0.7(5) . . . . ?
C11A N3A C13A O2A 178.9(4) . . . . ?
C11A N3A C13A N4A -2.8(4) . . . . ?
C11A C2A C3A N1A 178.4(4) . . . . ?
C13A N4A C15A C20A -12.9(6) . . . . ?
C13A N4A C15A C16A 169.4(4) . . . . ?
C13A N4A C12A C11A 9.1(4) . . . . ?
C13A N3A C11A C12A 8.1(4) . . . . ?
C13A N3A C11A C2A -117.2(4) . . . . ?
C2A N2A C1A O1A -178.1(4) . . . . ?
C2A N2A C1A N1A 1.7(4) . . . . ?
C2A N2A C5A C6A 86.6(5) . . . . ?
C2A N2A C5A C10A -93.5(5) . . . . ?
C20A C15A C16A C17A -1.8(6) . . . . ?
C16B C15B C20B C19B 1.2(6) . . . . ?
C16B C17B C18B C19B 1.4(6) . . . . ?
C20B C15B C16B C17B -0.6(6) . . . . ?
C5A N2A C1A O1A 7.0(6) . . . . ?
C5A N2A C1A N1A -173.2(3) . . . . ?
C5A N2A C2A C11A -4.9(6) . . . . ?
C5A N2A C2A C3A 173.2(4) . . . . ?
C5A C6A C7A C8A -1.0(6) . . . . ?
C5A C10A C9A C8A -0.2(7) . . . . ?
C17B C18B C19B C20B -0.9(6) . . . . ?
C6B C5B C10B C9B -1.9(6) . . . . ?
C6B C7B C8B C9B -1.1(8) . . . . ?
C14B N3B C13B O2B 3.6(6) . . . . ?
C14B N3B C13B N4B -177.7(3) . . . . ?
C14B N3B C11B C2B 56.1(5) . . . . ?
C14B N3B C11B C12B -178.4(3) . . . . ?
C5B N2B C2B C3B 177.4(4) . . . . ?
C5B N2B C2B C11B 0.8(6) . . . . ?
C5B N2B C1B O1B 4.6(6) . . . . ?
C5B N2B C1B N1B -177.5(4) . . . . ?
C5B C6B C7B C8B 0.1(7) . . . . ?
C5B C10B C9B C8B 0.8(7) . . . . ?
C16A C15A C20A C19A 2.6(6) . . . . ?
C16A C17A C18A C19A 2.6(7) . . . . ?
C4A N1A C1A O1A 1.1(6) . . . . ?
C4A N1A C1A N2A -178.7(3) . . . . ?
C4A N1A C3A C2A 177.8(4) . . . . ?
C6A C5A C10A C9A -1.0(6) . . . . ?
C6A C7A C8A C9A -0.2(7) . . . . ?
C18A C17A C16A C15A -0.8(7) . . . . ?
C14A N3A C11A C12A -177.3(4) . . . . ?
C14A N3A C11A C2A 57.3(5) . . . . ?
C14A N3A C13A O2A 4.4(6) . . . . ?
C14A N3A C13A N4A -177.4(3) . . . . ?
C10B C9B C8B C7B 0.6(8) . . . . ?
C10A C5A C6A C7A 1.6(6) . . . . ?
C10A C9A C8A C7A 0.8(7) . . . . ?
C4B N1B C3B C2B 177.4(4) . . . . ?
C4B N1B C1B O1B 0.6(7) . . . . ?
C4B N1B C1B N2B -177.3(4) . . . . ?
C3A N1A C1A O1A 178.3(4) . . . . ?
C3A N1A C1A N2A -1.5(4) . . . . ?
C7B C6B C5B N2B -177.3(4) . . . . ?
C7B C6B C5B C10B 1.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_dp21_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2164573'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of
Russia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(10cS,13aS,13bR)-2,11-dimethyl-13-(naphthalen-2-yl)-1,10c,11,13,13a,13b-hexahydro-3H-benzo[f]diimidazo[1,5-a:4',5'-c]quinoline-3,12(2H)-dione
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H24 N4 O2'
_chemical_formula_sum            'C28 H24 N4 O2'
_chemical_formula_weight         448.51
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100.00
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'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.118(4)
_cell_length_b                   10.799(4)
_cell_length_c                   10.873(5)
_cell_angle_alpha                90.043(14)
_cell_angle_beta                 100.093(12)
_cell_angle_gamma                95.192(12)
_cell_volume                     1049.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5828
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1898 before and 0.0936 after correction.
The Ratio of minimum to maximum transmission is 0.7812.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.381
_exptl_crystal_size_min          0.262
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         1.894
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3305
_reflns_number_total             4584
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.029
_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)+(0.0475P)²+0.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C9(H9), C6(H6), C22(H22), C25(H25), C28(H28), C27(H27), C7(H7),
 C23(H23), C12(H12), C10(H10), C24(H24), C11(H11)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.69665(13) 0.32976(10) 0.00336(10) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.95541(13) 0.66356(10) 0.62711(10) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.66014(14) 0.50863(11) 0.11063(11) 0.0177(3) Uani 1 1 d . . . . .
N1 N 0.64509(15) 0.32600(11) 0.20372(11) 0.0203(3) Uani 1 1 d . . . . .
N4 N 0.81064(15) 0.55976(12) 0.45052(11) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.97373(15) 0.71885(12) 0.42603(12) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.71850(17) 0.60205(14) 0.03557(13) 0.0186(3) Uani 1 1 d . . . . .
C13 C 0.73853(18) 0.81951(14) -0.02202(14) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.85185(18) 0.79690(15) -0.09165(14) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.67071(18) 0.38202(14) 0.09606(14) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.67071(18) 0.71937(14) 0.03840(14) 0.0195(3) Uani 1 1 d . . . . .
H14 H 0.591360 0.733218 0.081402 0.023 Uiso 1 1 calc R U . . .
C20 C 0.61819(17) 0.38906(14) 0.42183(14) 0.0186(3) Uani 1 1 d . . . . .
C19 C 0.72761(17) 0.46314(14) 0.50069(14) 0.0185(3) Uani 1 1 d . . . . .
C17 C 0.91706(17) 0.64914(14) 0.51399(14) 0.0191(3) Uani 1 1 d . . . . .
C21 C 0.52993(17) 0.29325(14) 0.47448(14) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.91828(19) 0.89760(15) -0.15223(14) 0.0256(4) Uani 1 1 d . . . . .
H9 H 0.992879 0.883322 -0.200263 0.031 Uiso 1 1 calc R U . . .
C26 C 0.56471(18) 0.26777(14) 0.60449(14) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.65496(17) 0.53557(14) 0.24235(13) 0.0178(3) Uani 1 1 d . . . . .
H2 H 0.591872 0.605135 0.250712 0.021 Uiso 1 1 calc R U . . .
C6 C 0.83116(18) 0.57985(15) -0.03404(14) 0.0208(3) Uani 1 1 d . . . . .
H6 H 0.862559 0.498634 -0.037903 0.025 Uiso 1 1 calc R U . . .
C3 C 0.58390(18) 0.41209(14) 0.28289(14) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.472981 0.408461 0.255625 0.023 Uiso 1 1 calc R U . . .
C16 C 0.89073(18) 0.69231(14) 0.30085(14) 0.0213(4) Uani 1 1 d . . . . .
H16A H 0.958434 0.690817 0.239047 0.026 Uiso 1 1 calc R U . . .
H16B H 0.817459 0.753826 0.275381 0.026 Uiso 1 1 calc R U . . .
C15 C 0.81244(18) 0.56289(14) 0.31599(13) 0.0190(3) Uani 1 1 d . . . . .
H15 H 0.876338 0.498457 0.294378 0.023 Uiso 1 1 calc R U . . .
C22 C 0.40616(18) 0.22067(15) 0.40312(15) 0.0230(4) Uani 1 1 d . . . . .
H22 H 0.377705 0.237124 0.316822 0.028 Uiso 1 1 calc R U . . .
C25 C 0.48296(18) 0.16905(15) 0.65549(15) 0.0231(4) Uani 1 1 d . . . . .
H25 H 0.509230 0.150626 0.741533 0.028 Uiso 1 1 calc R U . . .
C28 C 0.75456(18) 0.44208(15) 0.63175(14) 0.0219(4) Uani 1 1 d . . . . .
H28 H 0.826735 0.495528 0.685376 0.026 Uiso 1 1 calc R U . . .
C4 C 0.64385(19) 0.19306(14) 0.21740(15) 0.0242(4) Uani 1 1 d . . . . .
H4A H 0.673548 0.173682 0.305811 0.036 Uiso 1 1 calc R U . . .
H4B H 0.714252 0.161352 0.169274 0.036 Uiso 1 1 calc R U . . .
H4C H 0.542922 0.153842 0.186422 0.036 Uiso 1 1 calc R U . . .
C27 C 0.67785(18) 0.34622(15) 0.68048(14) 0.0220(4) Uani 1 1 d . . . . .
H27 H 0.700533 0.331382 0.767566 0.026 Uiso 1 1 calc R U . . .
C7 C 0.89484(19) 0.67443(15) -0.09557(14) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.969926 0.657761 -0.142233 0.027 Uiso 1 1 calc R U . . .
C23 C 0.3272(2) 0.12773(15) 0.45585(16) 0.0271(4) Uani 1 1 d . . . . .
H23 H 0.244390 0.081354 0.405984 0.033 Uiso 1 1 calc R U . . .
C12 C 0.69845(19) 0.94283(15) -0.01372(15) 0.0246(4) Uani 1 1 d . . . . .
H12 H 0.623184 0.959175 0.032885 0.029 Uiso 1 1 calc R U . . .
C10 C 0.8765(2) 1.01489(16) -0.14251(15) 0.0295(4) Uani 1 1 d . . . . .
H10 H 0.922164 1.081300 -0.183919 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3670(2) 0.09996(15) 0.58303(16) 0.0268(4) Uani 1 1 d . . . . .
H24 H 0.313509 0.033471 0.618230 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7663(2) 1.03848(15) -0.07166(15) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.739290 1.120704 -0.064157 0.034 Uiso 1 1 calc R U . . .
C18 C 1.06474(19) 0.83487(14) 0.45742(15) 0.0255(4) Uani 1 1 d . . . . .
H18A H 1.008141 0.904140 0.424358 0.038 Uiso 1 1 calc R U . . .
H18B H 1.155592 0.835308 0.420735 0.038 Uiso 1 1 calc R U . . .
H18C H 1.092236 0.843862 0.548449 0.038 Uiso 1 1 calc R U . . .


_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 C1 1.2236(18) . ?
O2 C17 1.2241(19) . ?
N2 C5 1.4223(19) . ?
N2 C1 1.390(2) . ?
N2 C2 1.4709(19) . ?
N1 C1 1.365(2) . ?
N1 C3 1.4756(19) . ?
N1 C4 1.443(2) . ?
N4 C19 1.401(2) . ?
N4 C17 1.394(2) . ?
N4 C15 1.4660(19) . ?
N3 C17 1.361(2) . ?
N3 C16 1.451(2) . ?
N3 C18 1.445(2) . ?
C5 C14 1.379(2) . ?
C5 C6 1.415(2) . ?
C13 C8 1.421(2) . ?
C13 C14 1.416(2) . ?
C13 C12 1.419(2) . ?
C8 C9 1.416(2) . ?
C8 C7 1.416(2) . ?
C14 H14 0.9500 . ?
C20 C19 1.387(2) . ?
C20 C21 1.434(2) . ?
C20 C3 1.514(2) . ?
C19 C28 1.425(2) . ?
C21 C26 1.426(2) . ?
C21 C22 1.422(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(2) . ?
C26 C25 1.415(2) . ?
C26 C27 1.417(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(2) . ?
C2 C15 1.520(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.363(2) . ?
C3 H3 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.533(2) . ?
C15 H15 1.0000 . ?
C22 H22 0.9500 . ?
C22 C23 1.367(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.364(2) . ?
C28 H28 0.9500 . ?
C28 C27 1.357(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C27 H27 0.9500 . ?
C7 H7 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.407(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.367(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.409(3) . ?
C24 H24 0.9500 . ?
C11 H11 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C5 N2 C2 120.17(12) . . ?
C1 N2 C5 124.28(13) . . ?
C1 N2 C2 108.87(12) . . ?
C1 N1 C3 110.76(12) . . ?
C1 N1 C4 121.34(13) . . ?
C4 N1 C3 126.12(13) . . ?
C19 N4 C15 120.38(12) . . ?
C17 N4 C19 128.23(13) . . ?
C17 N4 C15 110.55(12) . . ?
C17 N3 C16 112.52(13) . . ?
C17 N3 C18 121.92(13) . . ?
C18 N3 C16 121.64(13) . . ?
C14 C5 N2 118.49(14) . . ?
C14 C5 C6 119.63(14) . . ?
C6 C5 N2 121.72(14) . . ?
C14 C13 C8 119.34(14) . . ?
C14 C13 C12 121.98(15) . . ?
C12 C13 C8 118.67(14) . . ?
C9 C8 C13 118.84(15) . . ?
C7 C8 C13 118.22(14) . . ?
C7 C8 C9 122.93(15) . . ?
O1 C1 N2 126.45(14) . . ?
O1 C1 N1 126.04(14) . . ?
N1 C1 N2 107.50(13) . . ?
C5 C14 C13 120.78(15) . . ?
C5 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C19 C20 C21 119.07(14) . . ?
C19 C20 C3 121.47(14) . . ?
C21 C20 C3 119.36(13) . . ?
N4 C19 C28 120.16(14) . . ?
C20 C19 N4 119.42(14) . . ?
C20 C19 C28 120.41(14) . . ?
O2 C17 N4 127.62(14) . . ?
O2 C17 N3 125.30(14) . . ?
N3 C17 N4 107.08(13) . . ?
C26 C21 C20 119.82(14) . . ?
C22 C21 C20 123.17(14) . . ?
C22 C21 C26 117.02(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.84(16) . . ?
C10 C9 H9 119.6 . . ?
C25 C26 C21 119.97(15) . . ?
C25 C26 C27 121.57(14) . . ?
C27 C26 C21 118.41(14) . . ?
N2 C2 H2 111.5 . . ?
N2 C2 C3 101.62(11) . . ?
N2 C2 C15 110.26(12) . . ?
C3 C2 H2 111.5 . . ?
C15 C2 H2 111.5 . . ?
C15 C2 C3 110.13(13) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.32(15) . . ?
C7 C6 H6 119.8 . . ?
N1 C3 C20 115.33(13) . . ?
N1 C3 C2 99.45(12) . . ?
N1 C3 H3 109.0 . . ?
C20 C3 C2 114.70(12) . . ?
C20 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
N3 C16 H16A 111.4 . . ?
N3 C16 H16B 111.4 . . ?
N3 C16 C15 101.74(12) . . ?
H16A C16 H16B 109.3 . . ?
C15 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
N4 C15 C2 110.39(12) . . ?
N4 C15 C16 102.34(11) . . ?
N4 C15 H15 109.0 . . ?
C2 C15 C16 116.66(13) . . ?
C2 C15 H15 109.0 . . ?
C16 C15 H15 109.0 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.51(15) . . ?
C23 C22 H22 119.2 . . ?
C26 C25 H25 119.5 . . ?
C24 C25 C26 121.00(15) . . ?
C24 C25 H25 119.5 . . ?
C19 C28 H28 119.8 . . ?
C27 C28 C19 120.46(15) . . ?
C27 C28 H28 119.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.51(15) . . ?
C28 C27 H27 119.2 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.62(15) . . ?
C6 C7 H7 119.2 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.81(16) . . ?
C24 C23 H23 119.6 . . ?
C13 C12 H12 119.4 . . ?
C11 C12 C13 121.10(16) . . ?
C11 C12 H12 119.4 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.65(16) . . ?
C11 C10 H10 119.7 . . ?
C25 C24 C23 119.58(15) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C12 C11 C10 119.88(16) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N2 C5 C14 C13 172.11(13) . . . . ?
N2 C5 C6 C7 -173.76(14) . . . . ?
N2 C2 C3 N1 32.65(14) . . . . ?
N2 C2 C3 C20 156.28(13) . . . . ?
N2 C2 C15 N4 -166.25(12) . . . . ?
N2 C2 C15 C16 77.54(16) . . . . ?
N4 C19 C28 C27 -177.90(14) . . . . ?
N3 C16 C15 N4 22.98(15) . . . . ?
N3 C16 C15 C2 143.58(13) . . . . ?
C5 N2 C1 O1 -18.7(2) . . . . ?
C5 N2 C1 N1 161.98(13) . . . . ?
C5 N2 C2 C3 179.26(13) . . . . ?
C5 N2 C2 C15 -63.97(18) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C13 C8 C9 C10 1.1(2) . . . . ?
C13 C8 C7 C6 -0.5(2) . . . . ?
C13 C12 C11 C10 0.9(2) . . . . ?
C8 C13 C14 C5 3.3(2) . . . . ?
C8 C13 C12 C11 0.3(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C1 N2 C5 C14 164.57(14) . . . . ?
C1 N2 C5 C6 -20.0(2) . . . . ?
C1 N2 C2 C3 -28.21(16) . . . . ?
C1 N2 C2 C15 88.56(15) . . . . ?
C1 N1 C3 C20 -152.12(13) . . . . ?
C1 N1 C3 C2 -28.93(16) . . . . ?
C14 C5 C6 C7 1.6(2) . . . . ?
C14 C13 C8 C9 179.66(14) . . . . ?
C14 C13 C8 C7 -1.3(2) . . . . ?
C14 C13 C12 C11 179.30(15) . . . . ?
C20 C19 C28 C27 2.7(2) . . . . ?
C20 C21 C26 C25 -176.67(14) . . . . ?
C20 C21 C26 C27 5.7(2) . . . . ?
C20 C21 C22 C23 178.14(16) . . . . ?
C19 N4 C17 O2 -2.8(3) . . . . ?
C19 N4 C17 N3 176.57(14) . . . . ?
C19 N4 C15 C2 45.43(19) . . . . ?
C19 N4 C15 C16 170.27(13) . . . . ?
C19 C20 C21 C26 -5.9(2) . . . . ?
C19 C20 C21 C22 173.80(14) . . . . ?
C19 C20 C3 N1 103.06(17) . . . . ?
C19 C20 C3 C2 -11.6(2) . . . . ?
C19 C28 C27 C26 -2.8(2) . . . . ?
C17 N4 C19 C20 175.13(15) . . . . ?
C17 N4 C19 C28 -4.3(2) . . . . ?
C17 N4 C15 C2 -144.26(13) . . . . ?
C17 N4 C15 C16 -19.42(16) . . . . ?
C17 N3 C16 C15 -20.93(17) . . . . ?
C21 C20 C19 N4 -177.73(13) . . . . ?
C21 C20 C19 C28 1.7(2) . . . . ?
C21 C20 C3 N1 -80.65(18) . . . . ?
C21 C20 C3 C2 164.67(14) . . . . ?
C21 C26 C25 C24 -2.4(2) . . . . ?
C21 C26 C27 C28 -1.4(2) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C9 C8 C7 C6 178.54(15) . . . . ?
C9 C10 C11 C12 -1.2(2) . . . . ?
C26 C21 C22 C23 -2.2(2) . . . . ?
C26 C25 C24 C23 -0.5(2) . . . . ?
C2 N2 C5 C14 -47.3(2) . . . . ?
C2 N2 C5 C6 128.07(15) . . . . ?
C2 N2 C1 O1 -169.86(15) . . . . ?
C2 N2 C1 N1 10.84(17) . . . . ?
C6 C5 C14 C13 -3.4(2) . . . . ?
C3 N1 C1 O1 -166.81(15) . . . . ?
C3 N1 C1 N2 12.49(17) . . . . ?
C3 C20 C19 N4 -1.4(2) . . . . ?
C3 C20 C19 C28 177.99(14) . . . . ?
C3 C20 C21 C26 177.74(13) . . . . ?
C3 C20 C21 C22 -2.6(2) . . . . ?
C3 C2 C15 N4 -54.90(16) . . . . ?
C3 C2 C15 C16 -171.12(12) . . . . ?
C16 N3 C17 O2 -171.13(15) . . . . ?
C16 N3 C17 N4 9.47(18) . . . . ?
C15 N4 C19 C20 -16.4(2) . . . . ?
C15 N4 C19 C28 164.14(14) . . . . ?
C15 N4 C17 O2 -172.16(16) . . . . ?
C15 N4 C17 N3 7.22(17) . . . . ?
C15 C2 C3 N1 -84.22(14) . . . . ?
C15 C2 C3 C20 39.41(17) . . . . ?
C22 C21 C26 C25 3.6(2) . . . . ?
C22 C21 C26 C27 -173.96(14) . . . . ?
C22 C23 C24 C25 2.0(3) . . . . ?
C25 C26 C27 C28 -178.95(15) . . . . ?
C4 N1 C1 O1 -1.1(3) . . . . ?
C4 N1 C1 N2 178.19(14) . . . . ?
C4 N1 C3 C20 43.0(2) . . . . ?
C4 N1 C3 C2 166.21(14) . . . . ?
C27 C26 C25 C24 175.14(15) . . . . ?
C7 C8 C9 C10 -177.87(15) . . . . ?
C12 C13 C8 C9 -1.3(2) . . . . ?
C12 C13 C8 C7 177.73(14) . . . . ?
C12 C13 C14 C5 -175.75(14) . . . . ?
C18 N3 C17 O2 -13.1(3) . . . . ?
C18 N3 C17 N4 167.49(14) . . . . ?
C18 N3 C16 C15 -179.02(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_dp13_0m
_database_code_depnum_ccdc_archive 'CCDC 2164569'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of
Russia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-methyl-3-phenyl-1,3-dihydro-2H-imidazol-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H10 N2 O'
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100.00
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 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3685(3)
_cell_length_b                   7.0657(3)
_cell_length_c                   18.9967(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.181(2)
_cell_angle_gamma                90
_cell_volume                     848.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1476 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.9009.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.162
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22245
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_min         2.161
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1663
_reflns_number_total             1842
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v2021.4-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.111
_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)+(0.0388P)²+1.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C6(H6), C7(H7), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
O1 O 0.8191(2) 0.2443(2) 0.43862(7) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.6400(2) 0.2044(2) 0.53681(8) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.4536(2) 0.2982(2) 0.43849(8) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.8212(3) 0.1530(3) 0.58740(10) 0.0225(4) Uani 1 1 d . . . . .
H4A H 0.919288 0.075997 0.563631 0.034 Uiso 1 1 calc R U . . .
H4B H 0.773237 0.080270 0.626318 0.034 Uiso 1 1 calc R U . . .
H4C H 0.893362 0.268022 0.606377 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6568(3) 0.2498(3) 0.46787(9) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.3936(3) 0.3622(2) 0.36776(9) 0.0147(4) Uani 1 1 d . . . . .
C10 C 0.1831(3) 0.3450(3) 0.33803(9) 0.0169(4) Uani 1 1 d . . . . .
H10 H 0.082277 0.287792 0.364208 0.020 Uiso 1 1 calc R U . . .
C9 C 0.1216(3) 0.4123(3) 0.26979(9) 0.0194(4) Uani 1 1 d . . . . .
H9 H -0.021920 0.400785 0.249457 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2672(3) 0.4960(3) 0.23107(9) 0.0199(4) Uani 1 1 d . . . . .
H8 H 0.224048 0.542050 0.184529 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5414(3) 0.4448(3) 0.32915(9) 0.0160(4) Uani 1 1 d . . . . .
H6 H 0.685270 0.455303 0.349180 0.019 Uiso 1 1 calc R U . . .
C7 C 0.4770(3) 0.5118(3) 0.26100(10) 0.0195(4) Uani 1 1 d . . . . .
H7 H 0.577424 0.568948 0.234664 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4311(3) 0.2210(3) 0.54987(9) 0.0164(4) Uani 1 1 d . . . . .
H3 H 0.379180 0.195286 0.593655 0.020 Uiso 1 1 calc R U . . .
C2 C 0.3156(3) 0.2793(3) 0.49029(9) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.167734 0.303463 0.484085 0.020 Uiso 1 1 calc R U . . .


_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 C1 1.234(2) . ?
N1 C4 1.452(2) . ?
N1 C1 1.366(2) . ?
N1 C3 1.389(2) . ?
N2 C1 1.387(2) . ?
N2 C5 1.424(2) . ?
N2 C2 1.405(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.394(2) . ?
C5 C6 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.335(3) . ?
C2 H2 0.9500 . ?

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
C1 N1 C4 122.84(15) . . ?
C1 N1 C3 110.07(15) . . ?
C3 N1 C4 127.07(15) . . ?
C1 N2 C5 125.79(15) . . ?
C1 N2 C2 109.18(14) . . ?
C2 N2 C5 125.02(15) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C1 N1 126.52(17) . . ?
O1 C1 N2 128.23(16) . . ?
N1 C1 N2 105.24(15) . . ?
C10 C5 N2 119.06(16) . . ?
C6 C5 N2 120.75(16) . . ?
C6 C5 C10 120.18(16) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.52(17) . . ?
C9 C10 H10 120.2 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.75(17) . . ?
C8 C9 H9 119.6 . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.35(17) . . ?
C7 C8 H8 120.3 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.53(17) . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.66(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N1 C3 H3 125.9 . . ?
C2 C3 N1 108.23(15) . . ?
C2 C3 H3 125.9 . . ?
N2 C2 H2 126.4 . . ?
C3 C2 N2 107.27(16) . . ?
C3 C2 H2 126.4 . . ?

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
_geom_hbond_publ_flag
C10 H10 O1 0.95 2.34 3.262(2) 162.2 1_455 yes
C6 H6 O1 0.95 2.34 2.922(2) 119.1 . yes

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 C3 C2 N2 0.5(2) . . . . ?
N2 C5 C10 C9 178.06(16) . . . . ?
N2 C5 C6 C7 -177.86(16) . . . . ?
C4 N1 C1 O1 4.0(3) . . . . ?
C4 N1 C1 N2 -177.26(16) . . . . ?
C4 N1 C3 C2 177.15(17) . . . . ?
C1 N1 C3 C2 -0.9(2) . . . . ?
C1 N2 C5 C10 158.55(17) . . . . ?
C1 N2 C5 C6 -22.9(3) . . . . ?
C1 N2 C2 C3 0.0(2) . . . . ?
C5 N2 C1 O1 -3.6(3) . . . . ?
C5 N2 C1 N1 177.74(16) . . . . ?
C5 N2 C2 C3 -178.32(16) . . . . ?
C5 C10 C9 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C3 N1 C1 O1 -177.76(18) . . . . ?
C3 N1 C1 N2 0.9(2) . . . . ?
C2 N2 C1 O1 178.07(19) . . . . ?
C2 N2 C1 N1 -0.60(19) . . . . ?
C2 N2 C5 C10 -23.4(3) . . . . ?
C2 N2 C5 C6 155.18(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_dp10_0m_c
_database_code_depnum_ccdc_archive 'CCDC 2164572'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of
Russia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(3aS,3bS,11bS)-10-bromo-3-(4-bromophenyl)-1,5-dimethyl-1,3a,3b,4,5,11b-hexahydro-2H-diimidazo[1,5-a:4',5'-c]quinoline-2,6(3H)-dione
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 Br2 N4 O2'
_chemical_formula_sum            'C20 H18 Br2 N4 O2'
_chemical_formula_weight         506.20
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100.00
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'
Br Br -0.2901 2.4595 '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 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .
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                   14.616(3)
_cell_length_b                   9.5381(15)
_cell_length_c                   15.044(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.626(5)
_cell_angle_gamma                90
_cell_volume                     1858.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9042
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.75
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.388
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5824
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1302 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7807.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53022
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.626
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3519
_reflns_number_total             4055
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.034
_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)+(0.0237P)²+1.8345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0584
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C20(H20), C19(H19), C17(H17), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C14(H14A,H14B,H14C)
;
_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
Br1 Br 0.58557(2) 0.89569(3) 0.75357(2) 0.02385(7) Uani 1 1 d . . . . .
Br2 Br 0.85013(2) 0.83275(3) 0.00075(2) 0.02518(7) Uani 1 1 d . . . . .
O1 O 0.88554(13) 0.61402(19) 0.54590(12) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.49487(12) 0.50427(17) 0.13007(12) 0.0221(3) Uani 1 1 d . . . . .
N2 N 0.75881(14) 0.7833(2) 0.46247(13) 0.0182(4) Uani 1 1 d . . . . .
N4 N 0.60440(13) 0.68617(19) 0.22053(13) 0.0167(4) Uani 1 1 d . . . . .
N3 N 0.47784(13) 0.6247(2) 0.25428(14) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.64417(16) 0.8632(2) 0.66609(16) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.62492(16) 0.9562(2) 0.58948(16) 0.0189(4) Uani 1 1 d . . . . .
H9 H 0.584466 1.037580 0.581915 0.023 Uiso 1 1 calc R U . . .
C10 C 0.66477(16) 0.9309(2) 0.52331(16) 0.0190(4) Uani 1 1 d . . . . .
H10 H 0.651447 0.995133 0.470436 0.023 Uiso 1 1 calc R U . . .
C5 C 0.72443(16) 0.8113(2) 0.53401(16) 0.0163(4) Uani 1 1 d . . . . .
C2 C 0.71263(16) 0.8480(2) 0.36331(15) 0.0164(4) Uani 1 1 d . . . . .
H2 H 0.709882 0.951820 0.370956 0.020 Uiso 1 1 calc R U . . .
C11 C 0.60320(16) 0.7944(2) 0.28963(16) 0.0174(4) Uani 1 1 d . . . . .
H11 H 0.561829 0.875714 0.248837 0.021 Uiso 1 1 calc R U . . .
C15 C 0.65786(16) 0.7136(2) 0.16512(16) 0.0163(4) Uani 1 1 d . . . . .
C20 C 0.62356(17) 0.6721(2) 0.06592(16) 0.0186(4) Uani 1 1 d . . . . .
H20 H 0.561179 0.620538 0.031735 0.022 Uiso 1 1 calc R U . . .
C19 C 0.68166(17) 0.7069(2) 0.01748(16) 0.0193(4) Uani 1 1 d . . . . .
H19 H 0.659567 0.677896 -0.049817 0.023 Uiso 1 1 calc R U . . .
C1 C 0.83465(17) 0.6864(2) 0.47328(17) 0.0204(5) Uani 1 1 d . . . . .
N1 N 0.84049(14) 0.6876(2) 0.38508(14) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.92325(18) 0.6157(3) 0.37663(18) 0.0300(6) Uani 1 1 d . . . . .
H4A H 0.982772 0.678543 0.397868 0.045 Uiso 1 1 calc R U . . .
H4B H 0.899802 0.587551 0.306758 0.045 Uiso 1 1 calc R U . . .
H4C H 0.943253 0.532277 0.419548 0.045 Uiso 1 1 calc R U . . .
C3 C 0.79338(16) 0.8141(2) 0.32709(16) 0.0187(5) Uani 1 1 d . . . . .
H3 H 0.845879 0.890814 0.347890 0.022 Uiso 1 1 calc R U . . .
C16 C 0.75021(17) 0.7873(2) 0.21616(16) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.80662(17) 0.8235(2) 0.16650(17) 0.0202(5) Uani 1 1 d . . . . .
H17 H 0.868925 0.875360 0.200224 0.024 Uiso 1 1 calc R U . . .
C18 C 0.77136(17) 0.7835(2) 0.06724(17) 0.0189(4) Uani 1 1 d . . . . .
C13 C 0.52158(16) 0.5959(2) 0.19375(16) 0.0171(4) Uani 1 1 d . . . . .
C14 C 0.41278(16) 0.5227(2) 0.26929(17) 0.0215(5) Uani 1 1 d . . . . .
H14A H 0.369986 0.474345 0.205906 0.032 Uiso 1 1 calc R U . . .
H14B H 0.368204 0.570606 0.292218 0.032 Uiso 1 1 calc R U . . .
H14C H 0.456166 0.454271 0.319903 0.032 Uiso 1 1 calc R U . . .
C12 C 0.54081(17) 0.7204(2) 0.33405(17) 0.0206(5) Uani 1 1 d . . . . .
H12A H 0.586383 0.669338 0.396333 0.025 Uiso 1 1 calc R U . . .
H12B H 0.497710 0.787633 0.348361 0.025 Uiso 1 1 calc R U . . .
C6 C 0.74540(16) 0.7200(2) 0.61384(16) 0.0182(4) Uani 1 1 d . . . . .
H6 H 0.787064 0.639465 0.622951 0.022 Uiso 1 1 calc R U . . .
C7 C 0.70575(16) 0.7465(2) 0.67949(16) 0.0183(4) Uani 1 1 d . . . . .
H7 H 0.720711 0.684585 0.733998 0.022 Uiso 1 1 calc R U . . .


_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
Br1 C8 1.899(2) . ?
Br2 C18 1.901(2) . ?
O1 C1 1.212(3) . ?
O2 C13 1.219(3) . ?
N2 C5 1.409(3) . ?
N2 C2 1.459(3) . ?
N2 C1 1.394(3) . ?
N4 C11 1.471(3) . ?
N4 C15 1.406(3) . ?
N4 C13 1.385(3) . ?
N3 C13 1.361(3) . ?
N3 C14 1.449(3) . ?
N3 C12 1.448(3) . ?
C8 C9 1.376(3) . ?
C8 C7 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C5 1.399(3) . ?
C5 C6 1.398(3) . ?
C2 H2 1.0000 . ?
C2 C11 1.551(3) . ?
C2 C3 1.546(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.530(3) . ?
C15 C20 1.393(3) . ?
C15 C16 1.395(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.392(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.379(3) . ?
C1 N1 1.369(3) . ?
N1 C4 1.447(3) . ?
N1 C3 1.460(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3 1.0000 . ?
C3 C16 1.507(3) . ?
C16 C17 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?

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
C5 N2 C2 122.75(17) . . ?
C1 N2 C5 125.67(19) . . ?
C1 N2 C2 111.46(17) . . ?
C15 N4 C11 118.71(17) . . ?
C13 N4 C11 110.29(17) . . ?
C13 N4 C15 126.47(18) . . ?
C13 N3 C14 120.93(19) . . ?
C13 N3 C12 111.51(17) . . ?
C12 N3 C14 120.32(18) . . ?
C9 C8 Br1 119.49(17) . . ?
C9 C8 C7 120.4(2) . . ?
C7 C8 Br1 120.10(17) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C5 120.4(2) . . ?
C5 C10 H10 119.8 . . ?
C10 C5 N2 119.43(19) . . ?
C6 C5 N2 121.62(19) . . ?
C6 C5 C10 118.92(19) . . ?
N2 C2 H2 109.0 . . ?
N2 C2 C11 115.23(17) . . ?
N2 C2 C3 101.82(17) . . ?
C11 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C11 112.46(17) . . ?
N4 C11 C2 112.97(17) . . ?
N4 C11 H11 108.2 . . ?
N4 C11 C12 100.95(17) . . ?
C2 C11 H11 108.2 . . ?
C12 C11 C2 117.78(18) . . ?
C12 C11 H11 108.2 . . ?
C20 C15 N4 123.98(19) . . ?
C20 C15 C16 120.6(2) . . ?
C16 C15 N4 115.43(19) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 C15 119.3(2) . . ?
C19 C20 H20 120.4 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
O1 C1 N2 127.2(2) . . ?
O1 C1 N1 126.2(2) . . ?
N1 C1 N2 106.55(19) . . ?
C1 N1 C4 120.77(19) . . ?
C1 N1 C3 111.24(18) . . ?
C4 N1 C3 121.40(19) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C3 H3 109.7 . . ?
N1 C3 C2 100.83(17) . . ?
N1 C3 H3 109.7 . . ?
N1 C3 C16 111.17(18) . . ?
C16 C3 C2 115.43(18) . . ?
C16 C3 H3 109.7 . . ?
C15 C16 C3 119.76(19) . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 C3 120.36(19) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C19 C18 Br2 120.02(17) . . ?
C19 C18 C17 121.0(2) . . ?
C17 C18 Br2 118.98(17) . . ?
O2 C13 N4 126.3(2) . . ?
O2 C13 N3 126.3(2) . . ?
N3 C13 N4 107.34(18) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C12 C11 101.96(17) . . ?
N3 C12 H12A 111.4 . . ?
N3 C12 H12B 111.4 . . ?
C11 C12 H12A 111.4 . . ?
C11 C12 H12B 111.4 . . ?
H12A C12 H12B 109.2 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?

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
Br1 C8 C9 C10 -177.98(16) . . . . ?
Br1 C8 C7 C6 177.70(16) . . . . ?
O1 C1 N1 C4 -10.5(4) . . . . ?
O1 C1 N1 C3 -162.4(2) . . . . ?
N2 C5 C6 C7 -176.4(2) . . . . ?
N2 C2 C11 N4 -97.5(2) . . . . ?
N2 C2 C11 C12 19.7(3) . . . . ?
N2 C2 C3 N1 25.84(19) . . . . ?
N2 C2 C3 C16 145.71(18) . . . . ?
N2 C1 N1 C4 169.9(2) . . . . ?
N2 C1 N1 C3 18.0(2) . . . . ?
N4 C11 C12 N3 -26.9(2) . . . . ?
N4 C15 C20 C19 178.9(2) . . . . ?
N4 C15 C16 C3 8.4(3) . . . . ?
N4 C15 C16 C17 -177.8(2) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C9 C8 C7 C6 -2.3(3) . . . . ?
C9 C10 C5 N2 176.1(2) . . . . ?
C9 C10 C5 C6 -1.7(3) . . . . ?
C10 C5 C6 C7 1.4(3) . . . . ?
C5 N2 C2 C11 -71.9(3) . . . . ?
C5 N2 C2 C3 166.13(18) . . . . ?
C5 N2 C1 O1 -2.5(4) . . . . ?
C5 N2 C1 N1 177.13(19) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C2 N2 C5 C10 -18.0(3) . . . . ?
C2 N2 C5 C6 159.7(2) . . . . ?
C2 N2 C1 O1 -178.7(2) . . . . ?
C2 N2 C1 N1 1.0(2) . . . . ?
C2 C11 C12 N3 -150.38(18) . . . . ?
C2 C3 C16 C15 -38.2(3) . . . . ?
C2 C3 C16 C17 148.0(2) . . . . ?
C11 N4 C15 C20 -141.8(2) . . . . ?
C11 N4 C15 C16 38.1(3) . . . . ?
C11 N4 C13 O2 172.1(2) . . . . ?
C11 N4 C13 N3 -10.2(2) . . . . ?
C11 C2 C3 N1 -98.06(19) . . . . ?
C11 C2 C3 C16 21.8(3) . . . . ?
C15 N4 C11 C2 -52.0(3) . . . . ?
C15 N4 C11 C12 -178.66(18) . . . . ?
C15 N4 C13 O2 16.5(3) . . . . ?
C15 N4 C13 N3 -165.73(19) . . . . ?
C15 C20 C19 C18 -0.9(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C20 C15 C16 C3 -171.6(2) . . . . ?
C20 C15 C16 C17 2.1(3) . . . . ?
C20 C19 C18 Br2 -179.37(16) . . . . ?
C20 C19 C18 C17 1.8(3) . . . . ?
C1 N2 C5 C10 166.2(2) . . . . ?
C1 N2 C5 C6 -16.0(3) . . . . ?
C1 N2 C2 C11 104.4(2) . . . . ?
C1 N2 C2 C3 -17.6(2) . . . . ?
C1 N1 C3 C2 -27.9(2) . . . . ?
C1 N1 C3 C16 -150.82(18) . . . . ?
N1 C3 C16 C15 75.8(2) . . . . ?
N1 C3 C16 C17 -97.9(2) . . . . ?
C4 N1 C3 C2 -179.63(19) . . . . ?
C4 N1 C3 C16 57.5(3) . . . . ?
C3 C2 C11 N4 18.6(3) . . . . ?
C3 C2 C11 C12 135.8(2) . . . . ?
C3 C16 C17 C18 172.5(2) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
C16 C17 C18 Br2 -179.53(17) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C13 N4 C11 C2 150.38(18) . . . . ?
C13 N4 C11 C12 23.7(2) . . . . ?
C13 N4 C15 C20 11.9(3) . . . . ?
C13 N4 C15 C16 -168.2(2) . . . . ?
C13 N3 C12 C11 23.5(2) . . . . ?
C14 N3 C13 O2 18.2(3) . . . . ?
C14 N3 C13 N4 -159.55(18) . . . . ?
C14 N3 C12 C11 174.01(18) . . . . ?
C12 N3 C13 O2 168.5(2) . . . . ?
C12 N3 C13 N4 -9.2(2) . . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_SAB1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2165308'
loop_
_audit_author_name
_audit_author_address
'Alexey Dobrynin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2022-04-08 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3aS,3bR,11bS)-3,5-bis(4-bromobenzyl)-1-phenyl-1,3a,3b,4,5,11b-hexahydro-2H-diimidazo[1,5-a:4',5'-c]quinoline-2,6(3H)-dione
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 Br2 N4 O2'
_chemical_melting_point          ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         658.39

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   9.6635(7)
_cell_length_b                   11.4629(8)
_cell_length_c                   14.1743(10)
_cell_angle_alpha                91.874(2)
_cell_angle_beta                 106.844(2)
_cell_angle_gamma                112.114(2)
_cell_volume                     1374.29(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.54
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    2.987
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37004
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.521
_diffrn_reflns_theta_max         27.943
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6591
_reflns_number_gt                4984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²+3.8551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6591
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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_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
C2 C -0.1029(4) 0.6683(3) 0.5005(3) 0.0203(7) Uani 1 1 d . . . . .
C4 C 0.1193(4) 0.6452(3) 0.6306(2) 0.0174(6) Uani 1 1 d . . . . .
C5 C 0.0363(4) 0.5997(3) 0.6972(2) 0.0211(7) Uani 1 1 d . . . . .
H5 H -0.0693 0.5924 0.6824 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1084(4) 0.5652(3) 0.7850(3) 0.0239(7) Uani 1 1 d . . . . .
H6 H 0.0508 0.5323 0.8291 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2633(4) 0.5783(3) 0.8088(3) 0.0246(7) Uani 1 1 d . . . . .
H7 H 0.3134 0.5572 0.8700 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3444(4) 0.6224(3) 0.7425(3) 0.0218(7) Uani 1 1 d . . . . .
H8 H 0.4502 0.6300 0.7586 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2757(4) 0.6559(3) 0.6529(2) 0.0184(6) Uani 1 1 d . . . . .
C10 C 0.3646(4) 0.6921(3) 0.5793(2) 0.0173(6) Uani 1 1 d . . . . .
H10 H 0.4089 0.6279 0.5710 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2654(4) 0.7024(3) 0.4765(2) 0.0172(6) Uani 1 1 d . . . . .
H11 H 0.2065 0.6171 0.4329 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1524(4) 0.7608(3) 0.4878(2) 0.0179(6) Uani 1 1 d . . . . .
H12 H 0.2135 0.8491 0.5265 0.021 Uiso 1 1 calc R U . . .
C13 C 0.0305(4) 0.7620(3) 0.3911(3) 0.0217(7) Uani 1 1 d . . . . .
H13A H 0.0638 0.8464 0.3691 0.026 Uiso 1 1 calc R U . . .
H13B H 0.0120 0.6958 0.3368 0.026 Uiso 1 1 calc R U . . .
C15 C -0.2643(4) 0.7017(3) 0.3469(3) 0.0250(7) Uani 1 1 d . . . . .
H15A H -0.3438 0.6870 0.3813 0.030 Uiso 1 1 calc R U . . .
H15B H -0.2938 0.6212 0.3032 0.030 Uiso 1 1 calc R U . . .
C16 C -0.2694(4) 0.8035(3) 0.2831(3) 0.0225(7) Uani 1 1 d . . . . .
C17 C -0.3208(4) 0.7729(3) 0.1796(3) 0.0276(8) Uani 1 1 d . . . . .
H17 H -0.3476 0.6885 0.1498 0.033 Uiso 1 1 calc R U . . .
C18 C -0.3336(4) 0.8639(3) 0.1189(3) 0.0272(8) Uani 1 1 d . . . . .
H18 H -0.3700 0.8422 0.0483 0.033 Uiso 1 1 calc R U . . .
C19 C -0.2926(4) 0.9859(3) 0.1632(3) 0.0225(7) Uani 1 1 d . . . . .
C20 C -0.2413(4) 1.0188(3) 0.2665(3) 0.0252(7) Uani 1 1 d . . . . .
H20 H -0.2148 1.1031 0.2963 0.030 Uiso 1 1 calc R U . . .
C21 C -0.2293(4) 0.9266(4) 0.3252(3) 0.0267(8) Uani 1 1 d . . . . .
H21 H -0.1928 0.9487 0.3959 0.032 Uiso 1 1 calc R U . . .
C24 C 0.5194(4) 0.8616(3) 0.5193(2) 0.0178(6) Uani 1 1 d . . . . .
C27 C 0.3631(4) 0.8175(3) 0.3409(2) 0.0194(6) Uani 1 1 d . . . . .
H27A H 0.4602 0.8877 0.3388 0.023 Uiso 1 1 calc R U . . .
H27B H 0.2777 0.8487 0.3256 0.023 Uiso 1 1 calc R U . . .
C28 C 0.3185(4) 0.7067(3) 0.2617(2) 0.0188(6) Uani 1 1 d . . . . .
C29 C 0.2570(5) 0.7158(3) 0.1618(3) 0.0256(7) Uani 1 1 d . . . . .
H29 H 0.2401 0.7901 0.1453 0.031 Uiso 1 1 calc R U . . .
C30 C 0.2201(5) 0.6189(4) 0.0860(3) 0.0317(9) Uani 1 1 d . . . . .
H30 H 0.1788 0.6265 0.0181 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2446(5) 0.5107(3) 0.1109(3) 0.0273(8) Uani 1 1 d . . . . .
C32 C 0.3024(4) 0.4975(3) 0.2088(3) 0.0221(7) Uani 1 1 d . . . . .
H32 H 0.3174 0.4224 0.2249 0.026 Uiso 1 1 calc R U . . .
C33 C 0.3387(4) 0.5958(3) 0.2839(2) 0.0205(7) Uani 1 1 d . . . . .
H33 H 0.3781 0.5869 0.3517 0.025 Uiso 1 1 calc R U . . .
C35 C 0.6288(4) 0.8505(3) 0.6938(2) 0.0166(6) Uani 1 1 d . . . . .
C36 C 0.7500(4) 0.8146(3) 0.6908(3) 0.0217(7) Uani 1 1 d . . . . .
H36 H 0.7436 0.7708 0.6305 0.026 Uiso 1 1 calc R U . . .
C37 C 0.8800(4) 0.8425(3) 0.7754(3) 0.0263(7) Uani 1 1 d . . . . .
H37 H 0.9626 0.8175 0.7737 0.032 Uiso 1 1 calc R U . . .
C38 C 0.8884(4) 0.9072(4) 0.8626(3) 0.0284(8) Uani 1 1 d . . . . .
H38 H 0.9779 0.9275 0.9206 0.034 Uiso 1 1 calc R U . . .
C39 C 0.7679(4) 0.9426(3) 0.8661(3) 0.0265(8) Uani 1 1 d . . . . .
H39 H 0.7744 0.9864 0.9264 0.032 Uiso 1 1 calc R U . . .
C40 C 0.6367(4) 0.9142(3) 0.7810(3) 0.0224(7) Uani 1 1 d . . . . .
H40 H 0.5536 0.9383 0.7830 0.027 Uiso 1 1 calc R U . . .
Br22 Br -0.30342(4) 1.11449(3) 0.08408(3) 0.02824(12) Uani 1 1 d . . . . .
Br34 Br 0.19569(6) 0.37617(4) 0.00874(3) 0.04130(14) Uani 1 1 d . . . . .
N1 N -0.1105(3) 0.7336(3) 0.4214(2) 0.0210(6) Uani 1 1 d . . . . .
N3 N 0.0516(3) 0.6807(3) 0.5409(2) 0.0171(5) Uani 1 1 d . . . . .
N23 N 0.3898(3) 0.7853(3) 0.4407(2) 0.0180(6) Uani 1 1 d . . . . .
N25 N 0.4944(3) 0.8215(3) 0.60673(19) 0.0173(5) Uani 1 1 d . . . . .
O14 O -0.2138(3) 0.6106(2) 0.52968(18) 0.0229(5) Uani 1 1 d . . . . .
O26 O 0.6360(3) 0.9491(2) 0.51370(17) 0.0201(5) 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
C2 O14 1.224(4) . ?
C2 N1 1.368(4) . ?
C2 N3 1.385(4) . ?
C4 N3 1.400(4) . ?
C4 C5 1.402(4) . ?
C4 C9 1.408(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.510(4) . ?
C10 N25 1.484(4) . ?
C10 C11 1.531(5) . ?
C10 H10 1.0000 . ?
C11 N23 1.459(4) . ?
C11 C12 1.521(4) . ?
C11 H11 1.0000 . ?
C12 N3 1.467(4) . ?
C12 C13 1.532(5) . ?
C12 H12 1.0000 . ?
C13 N1 1.470(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 N1 1.454(4) . ?
C15 C16 1.506(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.377(5) . ?
C16 C17 1.392(5) . ?
C17 C18 1.392(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(5) . ?
C19 Br22 1.897(4) . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C24 O26 1.220(4) . ?
C24 N23 1.370(4) . ?
C24 N25 1.390(4) . ?
C27 N23 1.448(4) . ?
C27 C28 1.507(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C33 1.390(5) . ?
C28 C29 1.392(5) . ?
C29 C30 1.385(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.375(5) . ?
C31 Br34 1.900(4) . ?
C32 C33 1.390(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C35 C40 1.382(4) . ?
C35 C36 1.391(5) . ?
C35 N25 1.428(4) . ?
C36 C37 1.385(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.383(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.394(5) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?

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
O14 C2 N1 125.4(3) . . ?
O14 C2 N3 127.0(3) . . ?
N1 C2 N3 107.6(3) . . ?
N3 C4 C5 122.2(3) . . ?
N3 C4 C9 118.0(3) . . ?
C5 C4 C9 119.8(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C4 118.3(3) . . ?
C8 C9 C10 119.7(3) . . ?
C4 C9 C10 121.9(3) . . ?
N25 C10 C9 114.8(3) . . ?
N25 C10 C11 100.4(2) . . ?
C9 C10 C11 114.4(3) . . ?
N25 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
N23 C11 C12 113.4(3) . . ?
N23 C11 C10 100.4(2) . . ?
C12 C11 C10 110.0(2) . . ?
N23 C11 H11 110.9 . . ?
C12 C11 H11 110.9 . . ?
C10 C11 H11 110.9 . . ?
N3 C12 C11 108.5(3) . . ?
N3 C12 C13 102.1(2) . . ?
C11 C12 C13 116.2(3) . . ?
N3 C12 H12 109.9 . . ?
C11 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
N1 C13 C12 101.9(3) . . ?
N1 C13 H13A 111.4 . . ?
C12 C13 H13A 111.4 . . ?
N1 C13 H13B 111.4 . . ?
C12 C13 H13B 111.4 . . ?
H13A C13 H13B 109.3 . . ?
N1 C15 C16 113.5(3) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C21 C16 C17 118.8(3) . . ?
C21 C16 C15 121.1(3) . . ?
C17 C16 C15 120.0(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 Br22 120.4(3) . . ?
C20 C19 Br22 118.3(3) . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C16 C21 C20 121.2(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
O26 C24 N23 126.2(3) . . ?
O26 C24 N25 126.0(3) . . ?
N23 C24 N25 107.8(3) . . ?
N23 C27 C28 113.2(3) . . ?
N23 C27 H27A 108.9 . . ?
C28 C27 H27A 108.9 . . ?
N23 C27 H27B 108.9 . . ?
C28 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C33 C28 C29 118.1(3) . . ?
C33 C28 C27 122.8(3) . . ?
C29 C28 C27 119.1(3) . . ?
C30 C29 C28 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 118.8(3) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C32 C31 C30 121.3(3) . . ?
C32 C31 Br34 118.7(3) . . ?
C30 C31 Br34 119.9(3) . . ?
C31 C32 C33 119.0(3) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C28 121.3(3) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?
C40 C35 C36 120.5(3) . . ?
C40 C35 N25 119.3(3) . . ?
C36 C35 N25 120.2(3) . . ?
C37 C36 C35 120.1(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 119.4(3) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C39 C38 C37 120.7(3) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 120.0(3) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C35 C40 C39 119.4(3) . . ?
C35 C40 H40 120.3 . . ?
C39 C40 H40 120.3 . . ?
C2 N1 C15 118.0(3) . . ?
C2 N1 C13 110.6(3) . . ?
C15 N1 C13 120.5(3) . . ?
C2 N3 C4 127.6(3) . . ?
C2 N3 C12 111.2(3) . . ?
C4 N3 C12 120.2(3) . . ?
C24 N23 C27 121.7(3) . . ?
C24 N23 C11 110.6(2) . . ?
C27 N23 C11 124.2(3) . . ?
C24 N25 C35 118.4(3) . . ?
C24 N25 C10 107.7(2) . . ?
C35 N25 C10 120.1(3) . . ?

_refine_diff_density_max         1.194
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.105

