# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_22_a
_database_code_depnum_ccdc_archive 'CCDC 2401625'
loop_
_audit_author_name
_audit_author_address
'Fei Zeng'
;Hunan University of Science and Engineering
China
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C H Cl3), C45 H36 N6 O3'
_chemical_formula_sum            'C48 H39 Cl9 N6 O3'
_chemical_formula_weight         1066.90
_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      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                   13.234(7)
_cell_length_b                   13.892(7)
_cell_length_c                   16.543(9)
_cell_angle_alpha                109.362(7)
_cell_angle_beta                 96.339(7)
_cell_angle_gamma                102.534(7)
_cell_volume                     2746(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.96
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0834 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.7983.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26432
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.331
_diffrn_ambient_temperature      296.15
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_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                3620
_reflns_number_total             9686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         9686
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.2085
_refine_ls_R_factor_gt           0.0918
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1475P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.3105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C20, O1, C7, N1, N2, C6, C43, C5, C8, C1, C40, H43A, H43B, C4, H8A, H8B, C9,
 H1, C2, C39, C42, C3, H4, C10, C14, H2, C38, H39, C41, H42, H3, H10, C11, C13,
 H14, C37, H38, H41, H11, C12, H13, C36, C15, N6, H36A, H36B, N3, H15A, H15B,
 C00O, C35, C00R, C16, O3, N5, C30, C34, O2, N4, C17, C21, C29, C31, C33, H34,
 C22, H17, C18, C26, H29A, H29B, H31, C32, H33, H22A, H22B, C23, H18, C19, H20,
 C25, C28, H32, C24, C27, H19, H25, H28, H24, H27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 Cl6, Cl4, C45, Cl5, H45
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 Cl1, C44, Cl2, Cl3, H44
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 Cl8, Cl7, C46, Cl9, H46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
3.a Ternary CH refined with riding coordinates:
 C44(H44), C45(H45), C46(H46)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C22(H22A,H22B), C29(H29A,H29B), C36(H36A,H36B),
 C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C28(H28),
  C31(H31), C32(H32), C33(H33), C34(H34), C38(H38), C39(H39), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27938(13) 0.65091(14) 0.09445(12) 0.1777(8) Uani 1 1 d . . . . .
Cl2 Cl 0.45654(13) 0.60769(11) 0.02069(8) 0.1530(6) Uani 1 1 d . . . . .
Cl3 Cl 0.41224(16) 0.80514(11) 0.04689(10) 0.1770(7) Uani 1 1 d . . . . .
C44 C 0.4087(3) 0.7050(3) 0.0872(2) 0.0911(14) Uani 1 1 d . . . . .
H44 H 0.453206 0.734629 0.145775 0.109 Uiso 1 1 calc R U . . .
Cl4 Cl 0.12128(16) 0.30630(11) 0.34003(11) 0.1839(8) Uani 1 1 d . . . . .
Cl5 Cl 0.28162(13) 0.24782(14) 0.42264(11) 0.1720(7) Uani 1 1 d . . . . .
Cl6 Cl 0.08028(13) 0.22044(12) 0.47074(10) 0.1686(7) Uani 1 1 d . . . . .
C45 C 0.1445(4) 0.2169(3) 0.3853(3) 0.1146(18) Uani 1 1 d . . . . .
H45 H 0.120416 0.145520 0.340290 0.138 Uiso 1 1 calc R U . . .
Cl7 Cl 0.15831(10) 0.89688(12) 0.78371(9) 0.1421(6) Uani 1 1 d . . . . .
Cl8 Cl 0.30952(15) 0.94324(11) 0.93994(9) 0.1676(6) Uani 1 1 d . . . . .
Cl9 Cl 0.26494(14) 1.11003(11) 0.88950(10) 0.1616(7) Uani 1 1 d . . . . .
C46 C 0.2766(3) 0.9808(3) 0.8538(2) 0.1061(15) Uani 1 1 d . . . . .
H46 H 0.333137 0.977842 0.820193 0.127 Uiso 1 1 calc R U . . .
O1 O 0.56848(17) 0.75735(18) 0.25194(14) 0.0781(7) Uani 1 1 d . . . . .
O2 O 0.46072(16) 0.93201(17) 0.75460(15) 0.0749(8) Uani 1 1 d . . . . .
O3 O 0.53856(19) 0.30034(18) 0.47666(16) 0.0902(8) Uani 1 1 d . . . . .
N1 N 0.7246(2) 0.70476(19) 0.25571(16) 0.0630(7) Uani 1 1 d . . . . .
N2 N 0.7331(2) 0.8730(2) 0.32477(17) 0.0673(7) Uani 1 1 d . . . . .
N3 N 0.6338(2) 1.0141(2) 0.75115(17) 0.0672(6) Uani 1 1 d . . . . .
N4 N 0.60995(19) 0.8980(2) 0.81670(17) 0.0658(6) Uani 1 1 d . . . . .
N5 N 0.66594(19) 0.38396(18) 0.60652(17) 0.0628(7) Uani 1 1 d . . . . .
N6 N 0.7207(2) 0.34376(18) 0.48147(16) 0.0625(7) Uani 1 1 d . . . . .
C00O C 0.6314(3) 0.3388(2) 0.5166(2) 0.0645(8) Uani 1 1 d . . . . .
C00R C 0.5576(2) 0.9464(2) 0.7721(2) 0.0640(7) Uani 1 1 d . . . . .
C1 C 0.9205(3) 0.7207(3) 0.2967(2) 0.0807(11) Uani 1 1 d . . . . .
H1 H 0.917001 0.649509 0.268791 0.097 Uiso 1 1 calc R U . . .
C2 C 1.0154(3) 0.7941(3) 0.3414(3) 0.0961(12) Uani 1 1 d . . . . .
H2 H 1.076900 0.772123 0.343107 0.115 Uiso 1 1 calc R U . . .
C3 C 1.0208(3) 0.8994(3) 0.3837(2) 0.0891(11) Uani 1 1 d . . . . .
H3 H 1.085785 0.946712 0.414072 0.107 Uiso 1 1 calc R U . . .
C4 C 0.9313(3) 0.9367(3) 0.3822(2) 0.0772(10) Uani 1 1 d . . . . .
H4 H 0.934785 1.007813 0.410250 0.093 Uiso 1 1 calc R U . . .
C5 C 0.8373(2) 0.8624(2) 0.33697(19) 0.0614(8) Uani 1 1 d . . . . .
C6 C 0.8306(2) 0.7564(2) 0.2946(2) 0.0654(8) Uani 1 1 d . . . . .
C7 C 0.6644(2) 0.7755(2) 0.27341(19) 0.0638(8) Uani 1 1 d . . . . .
C8 C 0.7030(3) 0.9702(2) 0.3564(2) 0.0725(8) Uani 1 1 d . . . . .
H8A H 0.640580 0.964895 0.316726 0.087 Uiso 1 1 calc R U . . .
H8B H 0.759285 1.027535 0.355693 0.087 Uiso 1 1 calc R U . . .
C9 C 0.6802(2) 0.9976(2) 0.4475(2) 0.0613(7) Uani 1 1 d . . . . .
C10 C 0.7159(3) 1.1014(2) 0.5071(2) 0.0697(9) Uani 1 1 d . . . . .
H10 H 0.755702 1.153408 0.490974 0.084 Uiso 1 1 calc R U . . .
C11 C 0.6938(3) 1.1277(2) 0.5882(2) 0.0737(8) Uani 1 1 d . . . . .
H11 H 0.718346 1.197859 0.626534 0.088 Uiso 1 1 calc R U . . .
C12 C 0.6356(2) 1.0532(2) 0.6157(2) 0.0631(7) Uani 1 1 d . . . . .
C13 C 0.6001(3) 0.9494(2) 0.5564(2) 0.0715(9) Uani 1 1 d . . . . .
H13 H 0.561391 0.897136 0.572918 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6213(3) 0.9230(2) 0.4739(2) 0.0749(9) Uani 1 1 d . . . . .
H14 H 0.595375 0.853293 0.434844 0.090 Uiso 1 1 calc R U . . .
C15 C 0.6123(3) 1.0829(3) 0.7073(2) 0.0791(8) Uani 1 1 d . . . . .
H15A H 0.654282 1.154631 0.741925 0.095 Uiso 1 1 calc R U . . .
H15B H 0.538545 1.082219 0.703958 0.095 Uiso 1 1 calc R U . . .
C16 C 0.7345(3) 1.0068(3) 0.7810(2) 0.0668(7) Uani 1 1 d . . . . .
C17 C 0.8325(3) 1.0576(3) 0.7768(3) 0.0906(11) Uani 1 1 d . . . . .
H17 H 0.842877 1.108108 0.750972 0.109 Uiso 1 1 calc R U . . .
C18 C 0.9170(3) 1.0303(3) 0.8133(3) 0.1068(9) Uani 1 1 d . . . . .
H18 H 0.984948 1.060360 0.808343 0.128 Uiso 1 1 calc R U . . .
C19 C 0.9036(3) 0.9614(4) 0.8556(3) 0.1072(9) Uani 1 1 d . . . . .
H19 H 0.962284 0.948017 0.881675 0.129 Uiso 1 1 calc R U . . .
C20 C 0.8028(3) 0.9103(3) 0.8604(3) 0.0934(11) Uani 1 1 d . . . . .
H20 H 0.792951 0.861768 0.888210 0.112 Uiso 1 1 calc R U . . .
C21 C 0.7185(3) 0.9340(3) 0.8228(2) 0.0676(7) Uani 1 1 d . . . . .
C22 C 0.5576(3) 0.8170(3) 0.8467(2) 0.0768(9) Uani 1 1 d . . . . .
H22A H 0.482536 0.811394 0.837880 0.092 Uiso 1 1 calc R U . . .
H22B H 0.583706 0.839000 0.908929 0.092 Uiso 1 1 calc R U . . .
C23 C 0.5732(2) 0.7089(2) 0.8011(2) 0.0643(7) Uani 1 1 d . . . . .
C24 C 0.5593(3) 0.6671(2) 0.7120(2) 0.0694(9) Uani 1 1 d . . . . .
H24 H 0.543263 0.707096 0.679640 0.083 Uiso 1 1 calc R U . . .
C25 C 0.5688(3) 0.5652(2) 0.6686(2) 0.0690(8) Uani 1 1 d . . . . .
H25 H 0.559811 0.538283 0.608024 0.083 Uiso 1 1 calc R U . . .
C26 C 0.5916(2) 0.5052(2) 0.7159(2) 0.0634(7) Uani 1 1 d . . . . .
C27 C 0.5979(3) 0.6486(3) 0.8474(2) 0.0829(10) Uani 1 1 d . . . . .
H27 H 0.609170 0.675835 0.908093 0.100 Uiso 1 1 calc R U . . .
C28 C 0.6063(3) 0.5474(3) 0.8041(2) 0.0812(10) Uani 1 1 d . . . . .
H28 H 0.622467 0.507395 0.836518 0.097 Uiso 1 1 calc R U . . .
C29 C 0.5958(3) 0.3929(3) 0.6683(2) 0.0771(9) Uani 1 1 d . . . . .
H29A H 0.618391 0.364154 0.711078 0.092 Uiso 1 1 calc R U . . .
H29B H 0.525118 0.350057 0.637394 0.092 Uiso 1 1 calc R U . . .
C30 C 0.7759(2) 0.4176(2) 0.6270(2) 0.0571(7) Uani 1 1 d . . . . .
C31 C 0.8452(3) 0.4651(3) 0.7054(2) 0.0743(10) Uani 1 1 d . . . . .
H31 H 0.821812 0.481303 0.758111 0.089 Uiso 1 1 calc R U . . .
C32 C 0.9528(3) 0.4883(3) 0.7030(3) 0.0872(11) Uani 1 1 d . . . . .
H32 H 1.002235 0.521107 0.755098 0.105 Uiso 1 1 calc R U . . .
C33 C 0.9864(3) 0.4638(3) 0.6258(3) 0.0934(12) Uani 1 1 d . . . . .
H33 H 1.058620 0.480062 0.626878 0.112 Uiso 1 1 calc R U . . .
C34 C 0.9173(3) 0.4155(3) 0.5454(2) 0.0803(10) Uani 1 1 d . . . . .
H34 H 0.941113 0.399538 0.492910 0.096 Uiso 1 1 calc R U . . .
C35 C 0.8095(2) 0.3924(2) 0.5481(2) 0.0560(7) Uani 1 1 d . . . . .
C36 C 0.7176(3) 0.3048(2) 0.3895(2) 0.0760(10) Uani 1 1 d . . . . .
H36A H 0.654850 0.246099 0.361543 0.091 Uiso 1 1 calc R U . . .
H36B H 0.778337 0.277322 0.379129 0.091 Uiso 1 1 calc R U . . .
C37 C 0.7174(2) 0.3856(2) 0.3461(2) 0.0592(7) Uani 1 1 d . . . . .
C38 C 0.7059(2) 0.4848(2) 0.3890(2) 0.0600(8) Uani 1 1 d . . . . .
H38 H 0.702902 0.506487 0.448058 0.072 Uiso 1 1 calc R U . . .
C39 C 0.6988(2) 0.5525(2) 0.34411(19) 0.0610(8) Uani 1 1 d . . . . .
H39 H 0.693660 0.620257 0.374492 0.073 Uiso 1 1 calc R U . . .
C40 C 0.6993(2) 0.5227(2) 0.2567(2) 0.0597(7) Uani 1 1 d . . . . .
C41 C 0.7227(3) 0.3570(3) 0.2587(2) 0.0733(9) Uani 1 1 d . . . . .
H41 H 0.733231 0.291338 0.229158 0.088 Uiso 1 1 calc R U . . .
C42 C 0.7126(3) 0.4241(3) 0.2139(2) 0.0735(9) Uani 1 1 d . . . . .
H42 H 0.714846 0.402373 0.154731 0.088 Uiso 1 1 calc R U . . .
C43 C 0.6842(3) 0.5923(2) 0.2057(2) 0.0733(10) Uani 1 1 d . . . . .
H43A H 0.719055 0.574398 0.156251 0.088 Uiso 1 1 calc R U . . .
H43B H 0.609419 0.576833 0.182774 0.088 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 C44 1.747(4) . ?
Cl2 C44 1.726(4) . ?
Cl3 C44 1.725(5) . ?
C44 H44 0.9800 . ?
Cl4 C45 1.711(5) . ?
Cl5 C45 1.760(5) . ?
Cl6 C45 1.721(5) . ?
C45 H45 0.9800 . ?
Cl7 C46 1.751(4) . ?
Cl8 C46 1.717(5) . ?
Cl9 C46 1.741(5) . ?
C46 H46 0.9800 . ?
O1 C7 1.226(4) . ?
O2 C00R 1.239(4) . ?
O3 C00O 1.238(4) . ?
N1 C6 1.398(4) . ?
N1 C7 1.373(4) . ?
N1 C43 1.447(4) . ?
N2 C5 1.418(4) . ?
N2 C7 1.383(3) . ?
N2 C8 1.438(4) . ?
N3 C00R 1.380(4) . ?
N3 C15 1.433(5) . ?
N3 C16 1.405(4) . ?
N4 C00R 1.377(5) . ?
N4 C21 1.395(4) . ?
N4 C22 1.449(5) . ?
N5 C00O 1.387(4) . ?
N5 C29 1.449(4) . ?
N5 C30 1.393(4) . ?
N6 C00O 1.371(4) . ?
N6 C35 1.389(4) . ?
N6 C36 1.428(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(5) . ?
C1 C6 1.386(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.384(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(5) . ?
C9 C10 1.390(4) . ?
C9 C14 1.377(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.351(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(5) . ?
C12 C13 1.389(4) . ?
C12 C15 1.518(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(5) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.357(5) . ?
C16 C21 1.395(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.395(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.355(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.511(5) . ?
C23 C24 1.368(4) . ?
C23 C27 1.372(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.399(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(5) . ?
C26 C28 1.353(4) . ?
C26 C29 1.513(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.386(5) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.366(4) . ?
C30 C35 1.385(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.399(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.359(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.389(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.402(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.520(5) . ?
C37 C38 1.376(4) . ?
C37 C41 1.381(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.391(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.367(4) . ?
C40 C42 1.378(5) . ?
C40 C43 1.509(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.387(5) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C44 H44 108.8 . . ?
Cl2 C44 Cl1 110.1(2) . . ?
Cl2 C44 H44 108.8 . . ?
Cl3 C44 Cl1 110.0(2) . . ?
Cl3 C44 Cl2 110.3(2) . . ?
Cl3 C44 H44 108.8 . . ?
Cl4 C45 Cl5 107.9(3) . . ?
Cl4 C45 Cl6 111.9(3) . . ?
Cl4 C45 H45 109.1 . . ?
Cl5 C45 H45 109.1 . . ?
Cl6 C45 Cl5 109.8(3) . . ?
Cl6 C45 H45 109.1 . . ?
Cl7 C46 H46 108.1 . . ?
Cl8 C46 Cl7 112.3(3) . . ?
Cl8 C46 Cl9 111.6(2) . . ?
Cl8 C46 H46 108.1 . . ?
Cl9 C46 Cl7 108.5(3) . . ?
Cl9 C46 H46 108.1 . . ?
C6 N1 C43 124.5(3) . . ?
C7 N1 C6 110.4(2) . . ?
C7 N1 C43 125.1(3) . . ?
C5 N2 C8 125.8(2) . . ?
C7 N2 C5 109.4(3) . . ?
C7 N2 C8 124.7(3) . . ?
C00R N3 C15 124.4(3) . . ?
C00R N3 C16 109.8(3) . . ?
C16 N3 C15 125.7(3) . . ?
C00R N4 C21 109.6(3) . . ?
C00R N4 C22 124.0(3) . . ?
C21 N4 C22 126.4(3) . . ?
C00O N5 C29 123.8(3) . . ?
C30 N5 C00O 110.0(3) . . ?
C30 N5 C29 126.2(3) . . ?
C00O N6 C35 109.7(3) . . ?
C00O N6 C36 122.9(3) . . ?
C35 N6 C36 127.4(3) . . ?
O3 C00O N5 126.6(3) . . ?
O3 C00O N6 127.3(3) . . ?
N6 C00O N5 106.1(3) . . ?
O2 C00R N3 126.9(3) . . ?
O2 C00R N4 126.5(3) . . ?
N4 C00R N3 106.7(3) . . ?
C2 C1 H1 121.1 . . ?
C2 C1 C6 117.8(3) . . ?
C6 C1 H1 121.1 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.8 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4 121.9 . . ?
C4 C5 N2 130.6(3) . . ?
C4 C5 C6 122.7(3) . . ?
C6 C5 N2 106.7(2) . . ?
C1 C6 N1 132.5(3) . . ?
C1 C6 C5 120.2(3) . . ?
C5 C6 N1 107.3(3) . . ?
O1 C7 N1 128.0(3) . . ?
O1 C7 N2 125.7(3) . . ?
N1 C7 N2 106.3(3) . . ?
N2 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
N2 C8 C9 114.2(3) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C10 C9 C8 120.3(3) . . ?
C14 C9 C8 122.0(3) . . ?
C14 C9 C10 117.7(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 117.3(3) . . ?
C11 C12 C15 121.6(3) . . ?
C13 C12 C15 121.1(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
N3 C15 C12 114.0(3) . . ?
N3 C15 H15A 108.7 . . ?
N3 C15 H15B 108.7 . . ?
C12 C15 H15A 108.7 . . ?
C12 C15 H15B 108.8 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 N3 131.7(4) . . ?
C17 C16 C21 122.0(4) . . ?
C21 C16 N3 106.3(3) . . ?
C16 C17 H17 121.7 . . ?
C16 C17 C18 116.7(4) . . ?
C18 C17 H17 121.7 . . ?
C17 C18 H18 118.9 . . ?
C19 C18 C17 122.3(4) . . ?
C19 C18 H18 118.9 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.9(4) . . ?
C21 C20 H20 121.1 . . ?
N4 C21 C16 107.7(3) . . ?
C20 C21 N4 131.9(4) . . ?
C20 C21 C16 120.4(3) . . ?
N4 C22 H22A 108.7 . . ?
N4 C22 H22B 108.7 . . ?
N4 C22 C23 114.1(3) . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 C27 118.2(3) . . ?
C27 C23 C22 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.3(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C29 119.5(3) . . ?
C28 C26 C25 118.8(3) . . ?
C28 C26 C29 121.8(3) . . ?
C23 C27 H27 119.8 . . ?
C23 C27 C28 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C28 C27 121.7(4) . . ?
C26 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
N5 C29 C26 114.0(3) . . ?
N5 C29 H29A 108.8 . . ?
N5 C29 H29B 108.8 . . ?
C26 C29 H29A 108.8 . . ?
C26 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C31 C30 N5 131.6(3) . . ?
C31 C30 C35 122.1(3) . . ?
C35 C30 N5 106.3(2) . . ?
C30 C31 H31 121.5 . . ?
C30 C31 C32 117.0(3) . . ?
C32 C31 H31 121.5 . . ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.2(3) . . ?
C33 C32 H32 119.4 . . ?
C32 C33 H33 118.6 . . ?
C32 C33 C34 122.7(4) . . ?
C34 C33 H33 118.6 . . ?
C33 C34 H34 122.0 . . ?
C33 C34 C35 115.9(4) . . ?
C35 C34 H34 122.0 . . ?
N6 C35 C34 131.0(3) . . ?
C30 C35 N6 107.9(3) . . ?
C30 C35 C34 121.1(3) . . ?
N6 C36 H36A 108.4 . . ?
N6 C36 H36B 108.4 . . ?
N6 C36 C37 115.3(3) . . ?
H36A C36 H36B 107.5 . . ?
C37 C36 H36A 108.4 . . ?
C37 C36 H36B 108.4 . . ?
C38 C37 C36 122.6(3) . . ?
C38 C37 C41 118.1(3) . . ?
C41 C37 C36 119.2(3) . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0(3) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.0 . . ?
C40 C39 C38 122.0(3) . . ?
C40 C39 H39 119.0 . . ?
C39 C40 C42 118.0(3) . . ?
C39 C40 C43 122.8(3) . . ?
C42 C40 C43 119.2(3) . . ?
C37 C41 H41 119.3 . . ?
C37 C41 C42 121.5(3) . . ?
C42 C41 H41 119.3 . . ?
C40 C42 C41 120.3(3) . . ?
C40 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
N1 C43 C40 114.4(3) . . ?
N1 C43 H43A 108.7 . . ?
N1 C43 H43B 108.7 . . ?
C40 C43 H43A 108.7 . . ?
C40 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C5 C6 N1 1.5(4) . . . . ?
N2 C5 C6 C1 -178.5(3) . . . . ?
N2 C8 C9 C10 138.1(3) . . . . ?
N2 C8 C9 C14 -44.0(4) . . . . ?
N3 C16 C17 C18 -179.5(3) . . . . ?
N3 C16 C21 N4 0.7(3) . . . . ?
N3 C16 C21 C20 -179.2(3) . . . . ?
N4 C22 C23 C24 -47.6(4) . . . . ?
N4 C22 C23 C27 134.7(3) . . . . ?
N5 C30 C31 C32 179.5(3) . . . . ?
N5 C30 C35 N6 -0.3(3) . . . . ?
N5 C30 C35 C34 -179.8(3) . . . . ?
N6 C36 C37 C38 -8.8(5) . . . . ?
N6 C36 C37 C41 175.1(3) . . . . ?
C00O N5 C29 C26 -109.8(3) . . . . ?
C00O N5 C30 C31 -179.4(4) . . . . ?
C00O N5 C30 C35 -0.2(3) . . . . ?
C00O N6 C35 C30 0.7(4) . . . . ?
C00O N6 C35 C34 -179.9(3) . . . . ?
C00O N6 C36 C37 91.6(4) . . . . ?
C00R N3 C15 C12 -112.3(3) . . . . ?
C00R N3 C16 C17 -179.3(3) . . . . ?
C00R N3 C16 C21 -1.2(3) . . . . ?
C00R N4 C21 C16 0.0(3) . . . . ?
C00R N4 C21 C20 179.9(3) . . . . ?
C00R N4 C22 C23 113.1(3) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C1 C6 N1 179.5(4) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N2 178.1(4) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 N1 -179.8(3) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C5 N2 C7 O1 178.8(3) . . . . ?
C5 N2 C7 N1 1.5(4) . . . . ?
C5 N2 C8 C9 -88.3(4) . . . . ?
C6 N1 C7 O1 -177.7(3) . . . . ?
C6 N1 C7 N2 -0.5(4) . . . . ?
C6 N1 C43 C40 61.9(4) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C7 N1 C6 C1 179.4(4) . . . . ?
C7 N1 C6 C5 -0.7(4) . . . . ?
C7 N1 C43 C40 -116.7(4) . . . . ?
C7 N2 C5 C4 179.6(4) . . . . ?
C7 N2 C5 C6 -1.9(4) . . . . ?
C7 N2 C8 C9 95.2(4) . . . . ?
C8 N2 C5 C4 2.7(6) . . . . ?
C8 N2 C5 C6 -178.8(3) . . . . ?
C8 N2 C7 O1 -4.3(5) . . . . ?
C8 N2 C7 N1 178.4(3) . . . . ?
C8 C9 C10 C11 178.2(3) . . . . ?
C8 C9 C14 C13 -179.1(3) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C10 C11 C12 C15 179.0(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C11 C12 C15 N3 -131.5(3) . . . . ?
C12 C13 C14 C9 1.4(6) . . . . ?
C13 C12 C15 N3 47.7(4) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C15 N3 C00R O2 2.3(5) . . . . ?
C15 N3 C00R N4 -177.4(3) . . . . ?
C15 N3 C16 C17 -0.7(5) . . . . ?
C15 N3 C16 C21 177.4(3) . . . . ?
C15 C12 C13 C14 -180.0(3) . . . . ?
C16 N3 C00R O2 -179.1(3) . . . . ?
C16 N3 C00R N4 1.2(3) . . . . ?
C16 N3 C15 C12 69.4(4) . . . . ?
C16 C17 C18 C19 -3.9(6) . . . . ?
C17 C16 C21 N4 179.0(3) . . . . ?
C17 C16 C21 C20 -0.9(5) . . . . ?
C17 C18 C19 C20 3.4(6) . . . . ?
C18 C19 C20 C21 -1.5(6) . . . . ?
C19 C20 C21 N4 -179.7(3) . . . . ?
C19 C20 C21 C16 0.2(5) . . . . ?
C21 N4 C00R O2 179.5(3) . . . . ?
C21 N4 C00R N3 -0.7(3) . . . . ?
C21 N4 C22 C23 -62.4(4) . . . . ?
C21 C16 C17 C18 2.6(5) . . . . ?
C22 N4 C00R O2 3.3(5) . . . . ?
C22 N4 C00R N3 -176.9(3) . . . . ?
C22 N4 C21 C16 176.1(3) . . . . ?
C22 N4 C21 C20 -4.0(5) . . . . ?
C22 C23 C24 C25 -177.1(3) . . . . ?
C22 C23 C27 C28 176.5(3) . . . . ?
C23 C24 C25 C26 0.6(5) . . . . ?
C23 C27 C28 C26 0.6(6) . . . . ?
C24 C23 C27 C28 -1.3(5) . . . . ?
C24 C25 C26 C28 -1.3(5) . . . . ?
C24 C25 C26 C29 176.6(3) . . . . ?
C25 C26 C28 C27 0.7(5) . . . . ?
C25 C26 C29 N5 53.8(4) . . . . ?
C27 C23 C24 C25 0.7(5) . . . . ?
C28 C26 C29 N5 -128.4(3) . . . . ?
C29 N5 C00O O3 -0.2(5) . . . . ?
C29 N5 C00O N6 -179.0(3) . . . . ?
C29 N5 C30 C31 0.2(6) . . . . ?
C29 N5 C30 C35 179.4(3) . . . . ?
C29 C26 C28 C27 -177.2(3) . . . . ?
C30 N5 C00O O3 179.4(3) . . . . ?
C30 N5 C00O N6 0.6(3) . . . . ?
C30 N5 C29 C26 70.7(4) . . . . ?
C30 C31 C32 C33 -0.4(6) . . . . ?
C31 C30 C35 N6 179.0(3) . . . . ?
C31 C30 C35 C34 -0.5(5) . . . . ?
C31 C32 C33 C34 0.5(7) . . . . ?
C32 C33 C34 C35 -0.5(6) . . . . ?
C33 C34 C35 N6 -178.9(3) . . . . ?
C33 C34 C35 C30 0.5(5) . . . . ?
C35 N6 C00O O3 -179.6(3) . . . . ?
C35 N6 C00O N5 -0.8(3) . . . . ?
C35 N6 C36 C37 -87.4(4) . . . . ?
C35 C30 C31 C32 0.5(5) . . . . ?
C36 N6 C00O O3 1.3(5) . . . . ?
C36 N6 C00O N5 -179.9(3) . . . . ?
C36 N6 C35 C30 179.8(3) . . . . ?
C36 N6 C35 C34 -0.8(5) . . . . ?
C36 C37 C38 C39 -175.5(3) . . . . ?
C36 C37 C41 C42 173.8(3) . . . . ?
C37 C38 C39 C40 2.3(5) . . . . ?
C37 C41 C42 C40 1.4(5) . . . . ?
C38 C37 C41 C42 -2.5(5) . . . . ?
C38 C39 C40 C42 -3.4(5) . . . . ?
C38 C39 C40 C43 175.7(3) . . . . ?
C39 C40 C42 C41 1.5(5) . . . . ?
C39 C40 C43 N1 31.6(5) . . . . ?
C41 C37 C38 C39 0.7(5) . . . . ?
C42 C40 C43 N1 -149.3(3) . . . . ?
C43 N1 C6 C1 0.7(6) . . . . ?
C43 N1 C6 C5 -179.4(3) . . . . ?
C43 N1 C7 O1 1.0(6) . . . . ?
C43 N1 C7 N2 178.2(3) . . . . ?
C43 C40 C42 C41 -177.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 424.2 119.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT026_22_a                
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: We tried many times to obtain the high-quanlity crystals, 
but failed. In the crystal, it is thin and the high anlge of diffraction 
is weak, thus the ratio observed/ unique reflecitons is low. but, the strucuture can 
be clearly determined. 
However, the structure can be clearly determined. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_11_a_a
_database_code_depnum_ccdc_archive 'CCDC 2401631'
loop_
_audit_author_name
_audit_author_address
'Fei Zeng'
;Hunan University of Science and Engineering
China
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Br2, C15 H12 N2 O'
_chemical_formula_sum            'C16 H14 Br2 N2 O'
_chemical_formula_weight         410.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   9.02(2)
_cell_length_b                   9.39(2)
_cell_length_c                   10.71(3)
_cell_angle_alpha                84.17(3)
_cell_angle_beta                 67.13(3)
_cell_angle_gamma                66.09(3)
_cell_volume                     763(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.52
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.619
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    5.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.6750.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7846
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_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           30.0
_diffrn_source_power             1.5
_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                1506
_reflns_number_total             3137
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      0.879
_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)+(0.0326P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0999
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30908(8) 0.98079(7) 0.16222(6) 0.0603(2) Uani 1 1 d . . . . .
Br2 Br 0.29865(10) 1.24368(8) 0.32866(7) 0.0789(3) Uani 1 1 d . . . . .
C31 C 0.2241(10) 1.1987(8) 0.1995(8) 0.0593(18) Uani 1 1 d . . . . .
H31A H 0.268(7) 1.241(6) 0.116(6) 0.058(19) Uiso 1 1 d . . . . .
H31B H 0.098(8) 1.240(6) 0.247(6) 0.07(2) Uiso 1 1 d . . . . .
O2 O 0.5833(5) 0.6226(4) 0.1082(4) 0.0499(10) Uani 1 1 d . . . . .
N004 N 0.6608(5) 0.3722(5) 0.1851(4) 0.0357(10) Uani 1 1 d . . . . .
N005 N 0.6539(5) 0.5587(5) 0.2992(4) 0.0356(10) Uani 1 1 d . . . . .
C16 C 0.7166(6) 0.3016(6) 0.2897(5) 0.0346(12) Uani 1 1 d . . . . .
C17 C 0.7643(7) 0.1522(7) 0.3277(6) 0.0464(15) Uani 1 1 d . . . . .
H17 H 0.776(6) 0.072(6) 0.278(5) 0.066(18) Uiso 1 1 d . . . . .
C18 C 0.8106(8) 0.1220(9) 0.4404(6) 0.0530(17) Uani 1 1 d . . . . .
H18 H 0.827(7) 0.037(6) 0.463(6) 0.049(19) Uiso 1 1 d . . . . .
C19 C 0.8018(8) 0.2401(8) 0.5134(6) 0.0546(17) Uani 1 1 d . . . . .
H19 H 0.844(7) 0.211(6) 0.576(6) 0.065(19) Uiso 1 1 d . . . . .
C20 C 0.7541(7) 0.3905(7) 0.4736(5) 0.0452(14) Uani 1 1 d . . . . .
H20 H 0.751981 0.469075 0.521461 0.054 Uiso 1 1 calc R U . . .
C21 C 0.7097(6) 0.4224(6) 0.3618(5) 0.0360(12) Uani 1 1 d . . . . .
C22 C 0.6508(8) 0.7092(7) 0.3283(6) 0.0414(14) Uani 1 1 d . . . . .
H22A H 0.635(5) 0.710(4) 0.419(4) 0.019(11) Uiso 1 1 d . . . . .
H22B H 0.551(6) 0.786(5) 0.320(5) 0.039(15) Uiso 1 1 d . . . . .
C23 C 0.8197(7) 0.7229(6) 0.2371(5) 0.0361(13) Uani 1 1 d . . . . .
C24 C 0.8245(8) 0.8087(7) 0.1238(6) 0.0447(14) Uani 1 1 d . . . . .
H24 H 0.717(6) 0.869(5) 0.105(5) 0.045(14) Uiso 1 1 d . . . . .
C25 C 0.9821(7) 0.8080(7) 0.0306(6) 0.0453(15) Uani 1 1 d . . . . .
H25 H 0.985(6) 0.872(5) -0.044(5) 0.036(14) Uiso 1 1 d . . . . .
C26 C 1.1365(7) 0.7237(6) 0.0482(5) 0.0369(13) Uani 1 1 d . . . . .
C27 C 1.1309(8) 0.6453(7) 0.1627(6) 0.0472(15) Uani 1 1 d . . . . .
H27 H 1.239(6) 0.589(5) 0.176(4) 0.033(13) Uiso 1 1 d . . . . .
C28 C 0.9740(8) 0.6467(7) 0.2576(6) 0.0479(15) Uani 1 1 d . . . . .
H28 H 0.974(6) 0.575(6) 0.328(5) 0.056(17) Uiso 1 1 d . . . . .
C29 C 0.6881(7) 0.2911(7) 0.0629(5) 0.0407(14) Uani 1 1 d . . . . .
H29A H 0.686(5) 0.188(5) 0.095(4) 0.020(11) Uiso 1 1 d . . . . .
H29B H 0.589(7) 0.350(6) 0.034(6) 0.08(2) Uiso 1 1 d . . . . .
C30 C 0.6276(6) 0.5293(7) 0.1879(5) 0.0407(13) 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
Br1 C31 1.896(8) . ?
Br2 C31 1.902(7) . ?
C31 H31A 0.95(5) . ?
C31 H31B 0.97(5) . ?
O2 C30 1.219(6) . ?
N004 C16 1.401(7) . ?
N004 C29 1.468(7) . ?
N004 C30 1.384(7) . ?
N005 C21 1.382(6) . ?
N005 C22 1.465(7) . ?
N005 C30 1.377(6) . ?
C16 C17 1.361(8) . ?
C16 C21 1.404(7) . ?
C17 H17 0.91(5) . ?
C17 C18 1.393(9) . ?
C18 H18 0.78(5) . ?
C18 C19 1.380(9) . ?
C19 H19 0.86(5) . ?
C19 C20 1.375(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(7) . ?
C22 H22A 0.93(4) . ?
C22 H22B 0.93(4) . ?
C22 C23 1.506(8) . ?
C23 C24 1.383(7) . ?
C23 C28 1.377(8) . ?
C24 H24 0.99(5) . ?
C24 C25 1.381(8) . ?
C25 H25 0.94(5) . ?
C25 C26 1.372(7) . ?
C26 C27 1.360(8) . ?
C26 C29 1.526(8) 2_765 ?
C27 H27 0.96(4) . ?
C27 C28 1.380(8) . ?
C28 H28 0.96(5) . ?
C29 H29A 1.00(4) . ?
C29 H29B 0.99(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 C31 Br2 111.6(4) . . ?
Br1 C31 H31A 107(3) . . ?
Br1 C31 H31B 109(3) . . ?
Br2 C31 H31A 110(3) . . ?
Br2 C31 H31B 102(3) . . ?
H31A C31 H31B 117(5) . . ?
C16 N004 C29 125.9(5) . . ?
C30 N004 C16 110.3(4) . . ?
C30 N004 C29 120.8(4) . . ?
C21 N005 C22 126.5(4) . . ?
C30 N005 C21 110.2(4) . . ?
C30 N005 C22 122.5(5) . . ?
N004 C16 C21 105.7(5) . . ?
C17 C16 N004 132.2(4) . . ?
C17 C16 C21 122.1(5) . . ?
C16 C17 H17 123(4) . . ?
C16 C17 C18 117.2(5) . . ?
C18 C17 H17 120(4) . . ?
C17 C18 H18 114(4) . . ?
C19 C18 C17 121.2(7) . . ?
C19 C18 H18 125(4) . . ?
C18 C19 H19 115(4) . . ?
C20 C19 C18 121.0(6) . . ?
C20 C19 H19 123(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
N005 C21 C16 107.7(5) . . ?
C20 C21 N005 132.5(5) . . ?
C20 C21 C16 119.8(5) . . ?
N005 C22 H22A 105(2) . . ?
N005 C22 H22B 107(3) . . ?
N005 C22 C23 110.3(4) . . ?
H22A C22 H22B 107(4) . . ?
C23 C22 H22A 112(2) . . ?
C23 C22 H22B 114(3) . . ?
C24 C23 C22 119.5(5) . . ?
C28 C23 C22 122.6(5) . . ?
C28 C23 C24 117.8(5) . . ?
C23 C24 H24 121(3) . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 118(3) . . ?
C24 C25 H25 121(3) . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25 118(3) . . ?
C25 C26 C29 120.6(5) . 2_765 ?
C27 C26 C25 118.6(5) . . ?
C27 C26 C29 120.7(5) . 2_765 ?
C26 C27 H27 118(3) . . ?
C26 C27 C28 120.9(6) . . ?
C28 C27 H27 121(3) . . ?
C23 C28 C27 121.1(6) . . ?
C23 C28 H28 117(3) . . ?
C27 C28 H28 120(3) . . ?
N004 C29 C26 109.4(4) . 2_765 ?
N004 C29 H29A 103(2) . . ?
N004 C29 H29B 109(3) . . ?
C26 C29 H29A 113(2) 2_765 . ?
C26 C29 H29B 111(3) 2_765 . ?
H29A C29 H29B 111(4) . . ?
O2 C30 N004 126.9(5) . . ?
O2 C30 N005 127.1(5) . . ?
N005 C30 N004 106.0(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
N004 C16 C17 C18 -178.8(5) . . . . ?
N004 C16 C21 N005 -0.8(5) . . . . ?
N004 C16 C21 C20 178.8(4) . . . . ?
N005 C22 C23 C24 100.4(6) . . . . ?
N005 C22 C23 C28 -76.2(6) . . . . ?
C16 N004 C29 C26 -88.7(6) . . . 2_765 ?
C16 N004 C30 O2 177.2(5) . . . . ?
C16 N004 C30 N005 -3.1(5) . . . . ?
C16 C17 C18 C19 2.4(9) . . . . ?
C17 C16 C21 N005 -178.8(4) . . . . ?
C17 C16 C21 C20 0.8(7) . . . . ?
C17 C18 C19 C20 -2.8(9) . . . . ?
C18 C19 C20 C21 2.1(8) . . . . ?
C19 C20 C21 N005 178.5(5) . . . . ?
C19 C20 C21 C16 -1.0(7) . . . . ?
C21 N005 C22 C23 91.7(6) . . . . ?
C21 N005 C30 O2 -177.7(5) . . . . ?
C21 N005 C30 N004 2.5(5) . . . . ?
C21 C16 C17 C18 -1.4(8) . . . . ?
C22 N005 C21 C16 -171.0(4) . . . . ?
C22 N005 C21 C20 9.5(8) . . . . ?
C22 N005 C30 O2 -7.3(7) . . . . ?
C22 N005 C30 N004 172.9(4) . . . . ?
C22 C23 C24 C25 -172.5(5) . . . . ?
C22 C23 C28 C27 171.5(5) . . . . ?
C23 C24 C25 C26 -0.4(8) . . . . ?
C24 C23 C28 C27 -5.2(8) . . . . ?
C24 C25 C26 C27 -2.7(8) . . . . ?
C24 C25 C26 C29 173.0(5) . . . 2_765 ?
C25 C26 C27 C28 1.8(8) . . . . ?
C26 C27 C28 C23 2.2(8) . . . . ?
C28 C23 C24 C25 4.3(7) . . . . ?
C29 N004 C16 C17 -19.3(8) . . . . ?
C29 N004 C16 C21 163.0(4) . . . . ?
C29 N004 C30 O2 15.5(7) . . . . ?
C29 N004 C30 N005 -164.8(4) . . . . ?
C29 C26 C27 C28 -173.9(5) 2_765 . . . ?
C30 N004 C16 C17 -179.8(5) . . . . ?
C30 N004 C16 C21 2.5(5) . . . . ?
C30 N004 C29 C26 70.0(6) . . . 2_765 ?
C30 N005 C21 C16 -1.1(5) . . . . ?
C30 N005 C21 C20 179.4(5) . . . . ?
C30 N005 C22 C23 -77.0(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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2401792'
loop_
_audit_author_name
_audit_author_address
'Fei Zeng'
;Hunan University of Science and Engineering
China
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, 2(C15 H12 N2 O)'
_chemical_formula_sum            'C31 H25 Cl3 N4 O2'
_chemical_formula_weight         591.90
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.696(7)
_cell_length_b                   10.737(2)
_cell_length_c                   17.724(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.638(3)
_cell_angle_gamma                90
_cell_volume                     5781(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.65
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9061.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.341
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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           30.0
_diffrn_source_power             1.5
_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                3021
_reflns_number_total             6561
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      0.998
_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)+(0.0691P)²+0.8050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30)
;
_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 0.63536(4) 0.69783(12) 0.74031(8) 0.1368(6) Uani 1 1 d . . . . .
Cl2 Cl 0.57715(5) 0.82787(15) 0.59436(8) 0.1439(6) Uani 1 1 d . . . . .
Cl3 Cl 0.56777(5) 0.85190(12) 0.74524(7) 0.1238(5) Uani 1 1 d . . . . .
C31 C 0.58213(12) 0.7524(4) 0.6833(2) 0.0783(10) Uani 1 1 d . . . . .
H31 H 0.561966 0.681199 0.667033 0.094 Uiso 1 1 calc R U . . .
O1 O 0.52654(7) 0.5113(2) 0.68209(12) 0.0587(6) Uani 1 1 d . . . . .
N3 N 0.45753(7) 0.4211(2) 0.63698(14) 0.0463(6) Uani 1 1 d . . . . .
N4 N 0.51457(7) 0.2975(2) 0.66612(14) 0.0500(6) Uani 1 1 d . . . . .
C1 C 0.56913(8) 0.4029(3) 0.45912(17) 0.0443(7) Uani 1 1 d . . . . .
C2 C 0.54623(9) 0.2945(3) 0.45557(19) 0.0531(8) Uani 1 1 d . . . . .
H2 H 0.531473 0.254157 0.404483 0.064 Uiso 1 1 calc R U . . .
C3 C 0.54480(9) 0.2448(3) 0.52602(19) 0.0535(8) Uani 1 1 d . . . . .
H3 H 0.529693 0.170819 0.522141 0.064 Uiso 1 1 calc R U . . .
C4 C 0.56566(9) 0.3043(3) 0.60249(18) 0.0489(7) Uani 1 1 d . . . . .
C5 C 0.58939(9) 0.4117(3) 0.60694(19) 0.0538(8) Uani 1 1 d . . . . .
H5 H 0.604154 0.452124 0.657985 0.065 Uiso 1 1 calc R U . . .
C6 C 0.59127(9) 0.4592(3) 0.53613(19) 0.0527(8) Uani 1 1 d . . . . .
H6 H 0.607793 0.530444 0.540453 0.063 Uiso 1 1 calc R U . . .
C7 C 0.55885(9) 0.2624(3) 0.67755(19) 0.0601(8) Uani 1 1 d . . . . .
H7A H 0.562386 0.172796 0.683851 0.072 Uiso 1 1 calc R U . . .
H7B H 0.580665 0.301123 0.727856 0.072 Uiso 1 1 calc R U . . .
C8 C 0.47173(11) 0.0957(3) 0.6245(2) 0.0624(9) Uani 1 1 d . . . . .
H8 H 0.495641 0.043061 0.636534 0.075 Uiso 1 1 calc R U . . .
C9 C 0.47721(9) 0.2226(3) 0.63652(17) 0.0477(7) Uani 1 1 d . . . . .
C10 C 0.50238(10) 0.4209(3) 0.66373(17) 0.0487(7) Uani 1 1 d . . . . .
C11 C 0.44120(9) 0.3002(3) 0.61861(16) 0.0453(7) Uani 1 1 d . . . . .
C12 C 0.39927(10) 0.2532(3) 0.58916(18) 0.0550(8) Uani 1 1 d . . . . .
H12 H 0.375286 0.305177 0.577986 0.066 Uiso 1 1 calc R U . . .
C13 C 0.39393(11) 0.1265(3) 0.5767(2) 0.0653(9) Uani 1 1 d . . . . .
H13 H 0.365850 0.092283 0.556448 0.078 Uiso 1 1 calc R U . . .
C14 C 0.42945(12) 0.0500(3) 0.5939(2) 0.0705(9) Uani 1 1 d . . . . .
H14 H 0.424823 -0.035172 0.584526 0.085 Uiso 1 1 calc R U . . .
C15 C 0.43270(9) 0.5372(3) 0.61921(18) 0.0521(8) Uani 1 1 d . . . . .
H15A H 0.446502 0.593890 0.666014 0.063 Uiso 1 1 calc R U . . .
H15B H 0.403026 0.520549 0.612319 0.063 Uiso 1 1 calc R U . . .
O2 O 0.32689(6) 0.4601(2) 0.58796(14) 0.0721(7) Uani 1 1 d . . . . .
N1 N 0.26313(8) 0.5643(2) 0.50248(16) 0.0520(6) Uani 1 1 d . . . . .
N2 N 0.27399(8) 0.5199(2) 0.63200(15) 0.0513(6) Uani 1 1 d . . . . .
C16 C 0.28243(11) 0.3461(3) 0.3809(2) 0.0665(9) Uani 1 1 d . . . . .
H16 H 0.312018 0.367432 0.401483 0.080 Uiso 1 1 calc R U . . .
C17 C 0.26876(11) 0.2284(3) 0.3486(2) 0.0655(9) Uani 1 1 d . . . . .
H17 H 0.289288 0.172016 0.346826 0.079 Uiso 1 1 calc R U . . .
C18 C 0.22533(10) 0.1930(3) 0.31897(18) 0.0531(8) Uani 1 1 d . . . . .
C19 C 0.19550(11) 0.2806(3) 0.3192(2) 0.0656(9) Uani 1 1 d . . . . .
H19 H 0.165856 0.259607 0.298150 0.079 Uiso 1 1 calc R U . . .
C20 C 0.20887(11) 0.3986(3) 0.3501(2) 0.0684(9) Uani 1 1 d . . . . .
H20 H 0.188094 0.456588 0.348908 0.082 Uiso 1 1 calc R U . . .
C21 C 0.25258(11) 0.4319(3) 0.38281(18) 0.0571(8) Uani 1 1 d . . . . .
C22 C 0.26817(11) 0.5570(3) 0.4256(2) 0.0669(9) Uani 1 1 d . . . . .
H22A H 0.298894 0.568863 0.437783 0.080 Uiso 1 1 calc R U . . .
H22B H 0.251314 0.623162 0.388157 0.080 Uiso 1 1 calc R U . . .
C23 C 0.29215(10) 0.5092(3) 0.5758(2) 0.0515(8) Uani 1 1 d . . . . .
C24 C 0.28848(10) 0.4394(3) 0.70565(19) 0.0646(9) Uani 1 1 d . . . . .
H24A H 0.275917 0.468794 0.742369 0.077 Uiso 1 1 calc R U . . .
H24B H 0.320282 0.443415 0.736127 0.077 Uiso 1 1 calc R U . . .
C25 C 0.23294(9) 0.5770(2) 0.59309(19) 0.0482(7) Uani 1 1 d . . . . .
C26 C 0.22629(9) 0.6049(2) 0.5121(2) 0.0500(7) Uani 1 1 d . . . . .
C27 C 0.18880(11) 0.6641(3) 0.4567(2) 0.0655(9) Uani 1 1 d . . . . .
H27 H 0.184313 0.682613 0.402291 0.079 Uiso 1 1 calc R U . . .
C28 C 0.15826(11) 0.6946(3) 0.4859(3) 0.0803(12) Uani 1 1 d . . . . .
H28 H 0.132642 0.735454 0.450283 0.096 Uiso 1 1 calc R U . . .
C29 C 0.16428(12) 0.6668(3) 0.5655(3) 0.0791(11) Uani 1 1 d . . . . .
H29 H 0.142615 0.688442 0.582351 0.095 Uiso 1 1 calc R U . . .
C30 C 0.20194(11) 0.6070(3) 0.6214(2) 0.0667(9) Uani 1 1 d . . . . .
H30 H 0.206138 0.588055 0.675588 0.080 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 C31 1.736(4) . ?
Cl2 C31 1.715(4) . ?
Cl3 C31 1.743(4) . ?
C31 H31 0.9800 . ?
O1 C10 1.217(3) . ?
N3 C10 1.374(3) . ?
N3 C11 1.393(3) . ?
N3 C15 1.457(3) . ?
N4 C7 1.465(3) . ?
N4 C9 1.391(3) . ?
N4 C10 1.382(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.379(4) . ?
C1 C15 1.507(4) 5_666 ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.386(4) . ?
C4 C7 1.513(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C8 C14 1.377(4) . ?
C9 C11 1.391(4) . ?
C11 C12 1.373(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O2 C23 1.215(3) . ?
N1 C22 1.447(4) . ?
N1 C23 1.376(4) . ?
N1 C26 1.394(3) . ?
N2 C23 1.382(4) . ?
N2 C24 1.462(4) . ?
N2 C25 1.393(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C16 C21 1.375(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(4) . ?
C18 C19 1.378(4) . ?
C18 C24 1.501(4) 7_556 ?
C19 H19 0.9300 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 C22 1.520(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.386(4) . ?
C25 C30 1.379(4) . ?
C26 C27 1.375(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.369(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(5) . ?
C30 H30 0.9300 . ?

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
Cl1 C31 Cl3 109.82(19) . . ?
Cl1 C31 H31 108.5 . . ?
Cl2 C31 Cl1 111.1(2) . . ?
Cl2 C31 Cl3 110.3(2) . . ?
Cl2 C31 H31 108.5 . . ?
Cl3 C31 H31 108.5 . . ?
C10 N3 C11 110.1(2) . . ?
C10 N3 C15 121.3(2) . . ?
C11 N3 C15 127.9(2) . . ?
C9 N4 C7 127.2(2) . . ?
C10 N4 C7 121.5(3) . . ?
C10 N4 C9 109.5(2) . . ?
C2 C1 C15 121.2(3) . 5_666 ?
C6 C1 C2 117.7(3) . . ?
C6 C1 C15 120.9(3) . 5_666 ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C7 121.2(3) . . ?
C5 C4 C7 120.0(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 121.3(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
N4 C7 C4 109.6(2) . . ?
N4 C7 H7A 109.8 . . ?
N4 C7 H7B 109.8 . . ?
C4 C7 H7A 109.8 . . ?
C4 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 H8 121.3 . . ?
C14 C8 H8 121.3 . . ?
C14 C8 C9 117.4(3) . . ?
C8 C9 N4 131.9(3) . . ?
C8 C9 C11 120.8(3) . . ?
C11 C9 N4 107.3(2) . . ?
O1 C10 N3 126.8(3) . . ?
O1 C10 N4 126.9(3) . . ?
N3 C10 N4 106.3(3) . . ?
C9 C11 N3 106.7(2) . . ?
C12 C11 N3 132.0(3) . . ?
C12 C11 C9 121.3(3) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.7(3) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C8 C14 H14 119.1 . . ?
C13 C14 C8 121.9(3) . . ?
C13 C14 H14 119.1 . . ?
N3 C15 C1 110.8(2) . 5_666 ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
C1 C15 H15A 109.5 5_666 . ?
C1 C15 H15B 109.5 5_666 . ?
H15A C15 H15B 108.1 . . ?
C23 N1 C22 122.7(3) . . ?
C23 N1 C26 109.0(3) . . ?
C26 N1 C22 127.3(3) . . ?
C23 N2 C24 120.9(2) . . ?
C23 N2 C25 109.5(2) . . ?
C25 N2 C24 125.4(2) . . ?
C17 C16 H16 119.8 . . ?
C21 C16 H16 119.8 . . ?
C21 C16 C17 120.5(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C24 121.1(3) . 7_556 ?
C19 C18 C24 120.8(3) . 7_556 ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 118.5(3) . . ?
C16 C21 C22 120.4(3) . . ?
C20 C21 C22 121.0(3) . . ?
N1 C22 C21 111.2(2) . . ?
N1 C22 H22A 109.4 . . ?
N1 C22 H22B 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
O2 C23 N1 126.2(3) . . ?
O2 C23 N2 126.9(3) . . ?
N1 C23 N2 106.8(3) . . ?
N2 C24 C18 111.0(2) . 7_556 ?
N2 C24 H24A 109.4 . . ?
N2 C24 H24B 109.4 . . ?
C18 C24 H24A 109.4 7_556 . ?
C18 C24 H24B 109.4 7_556 . ?
H24A C24 H24B 108.0 . . ?
C26 C25 N2 106.8(2) . . ?
C30 C25 N2 132.0(3) . . ?
C30 C25 C26 121.2(3) . . ?
C25 C26 N1 107.8(2) . . ?
C27 C26 N1 130.4(3) . . ?
C27 C26 C25 121.8(3) . . ?
C26 C27 H27 121.8 . . ?
C26 C27 C28 116.5(3) . . ?
C28 C27 H27 121.8 . . ?
C27 C28 H28 118.8 . . ?
C29 C28 C27 122.3(3) . . ?
C29 C28 H28 118.8 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C25 C30 C29 116.8(3) . . ?
C25 C30 H30 121.6 . . ?
C29 C30 H30 121.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C11 C12 C13 179.5(3) . . . . ?
N4 C9 C11 N3 0.6(3) . . . . ?
N4 C9 C11 C12 -179.0(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C2 C3 C4 C5 -2.6(4) . . . . ?
C2 C3 C4 C7 170.7(2) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C3 C4 C7 N4 -72.3(3) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C5 C4 C7 N4 100.9(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C7 N4 C9 C8 13.4(5) . . . . ?
C7 N4 C9 C11 -167.1(2) . . . . ?
C7 N4 C10 O1 -11.4(4) . . . . ?
C7 N4 C10 N3 169.0(2) . . . . ?
C7 C4 C5 C6 -172.0(2) . . . . ?
C8 C9 C11 N3 -179.8(2) . . . . ?
C8 C9 C11 C12 0.6(4) . . . . ?
C9 N4 C7 C4 97.2(3) . . . . ?
C9 N4 C10 O1 -177.1(3) . . . . ?
C9 N4 C10 N3 3.3(3) . . . . ?
C9 C8 C14 C13 -0.8(5) . . . . ?
C9 C11 C12 C13 -0.9(4) . . . . ?
C10 N3 C11 C9 1.5(3) . . . . ?
C10 N3 C11 C12 -179.0(3) . . . . ?
C10 N3 C15 C1 70.6(3) . . . 5_666 ?
C10 N4 C7 C4 -65.7(3) . . . . ?
C10 N4 C9 C8 178.0(3) . . . . ?
C10 N4 C9 C11 -2.5(3) . . . . ?
C11 N3 C10 O1 177.4(3) . . . . ?
C11 N3 C10 N4 -3.0(3) . . . . ?
C11 N3 C15 C1 -98.6(3) . . . 5_666 ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C8 0.4(5) . . . . ?
C14 C8 C9 N4 179.8(3) . . . . ?
C14 C8 C9 C11 0.3(4) . . . . ?
C15 N3 C10 O1 6.5(4) . . . . ?
C15 N3 C10 N4 -173.9(2) . . . . ?
C15 N3 C11 C9 171.7(2) . . . . ?
C15 N3 C11 C12 -8.8(5) . . . . ?
C15 C1 C2 C3 -174.6(2) 5_666 . . . ?
C15 C1 C6 C5 173.3(2) 5_666 . . . ?
N1 C26 C27 C28 -178.8(3) . . . . ?
N2 C25 C26 N1 0.2(3) . . . . ?
N2 C25 C26 C27 -179.0(2) . . . . ?
N2 C25 C30 C29 178.8(3) . . . . ?
C16 C17 C18 C19 2.7(5) . . . . ?
C16 C17 C18 C24 -172.0(3) . . . 7_556 ?
C16 C21 C22 N1 -109.0(3) . . . . ?
C17 C16 C21 C20 -1.5(5) . . . . ?
C17 C16 C21 C22 174.3(3) . . . . ?
C17 C18 C19 C20 -1.7(5) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
C19 C20 C21 C16 2.5(5) . . . . ?
C19 C20 C21 C22 -173.2(3) . . . . ?
C20 C21 C22 N1 66.7(4) . . . . ?
C21 C16 C17 C18 -1.2(5) . . . . ?
C22 N1 C23 O2 7.9(4) . . . . ?
C22 N1 C23 N2 -171.7(2) . . . . ?
C22 N1 C26 C25 170.2(2) . . . . ?
C22 N1 C26 C27 -10.7(5) . . . . ?
C23 N1 C22 C21 78.7(4) . . . . ?
C23 N1 C26 C25 1.3(3) . . . . ?
C23 N1 C26 C27 -179.6(3) . . . . ?
C23 N2 C24 C18 -68.5(3) . . . 7_556 ?
C23 N2 C25 C26 -1.6(3) . . . . ?
C23 N2 C25 C30 179.1(3) . . . . ?
C24 N2 C23 O2 -19.0(4) . . . . ?
C24 N2 C23 N1 160.6(2) . . . . ?
C24 N2 C25 C26 -158.6(2) . . . . ?
C24 N2 C25 C30 22.1(5) . . . . ?
C24 C18 C19 C20 173.0(3) 7_556 . . . ?
C25 N2 C23 O2 -177.2(3) . . . . ?
C25 N2 C23 N1 2.3(3) . . . . ?
C25 N2 C24 C18 86.2(3) . . . 7_556 ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 N1 C22 C21 -88.8(4) . . . . ?
C26 N1 C23 O2 177.4(3) . . . . ?
C26 N1 C23 N2 -2.2(3) . . . . ?
C26 C25 C30 C29 -0.4(4) . . . . ?
C26 C27 C28 C29 -0.7(5) . . . . ?
C27 C28 C29 C30 0.6(5) . . . . ?
C28 C29 C30 C25 0.0(5) . . . . ?
C30 C25 C26 N1 179.6(3) . . . . ?
C30 C25 C26 C27 0.4(4) . . . . ?

_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_11_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2401626'
loop_
_audit_author_name
_audit_author_address
'Fei Zeng'
;Hunan University of Science and Engineering
China
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-09-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C45 H36 N6 O3'
_chemical_formula_sum            'C46 H38 Cl2 N6 O3'
_chemical_formula_weight         793.72
_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      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                   12.106(6)
_cell_length_b                   13.118(6)
_cell_length_c                   13.961(7)
_cell_angle_alpha                76.807(6)
_cell_angle_beta                 75.289(6)
_cell_angle_gamma                84.733(7)
_cell_volume                     2086.7(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.66
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0700 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8220.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20197
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.543
_diffrn_ambient_temperature      296.15
_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_source_current           30.0
_diffrn_source_power             1.5
_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                3105
_reflns_number_total             7357
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7357
_refine_ls_number_restraints     468
_refine_ls_R_factor_all          0.2213
_refine_ls_R_factor_gt           0.1270
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3448
_refine_ls_wR_factor_ref         0.4085
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C39, O1, C9, N2, N1, C8, C10, C15, C16, H8A, H8B, C5, C11, C14, H16A, H16B,
 C17, C4, C6, H11, C12, C13, H14, C18, C21, C3, H4, H6, C7, H12, H13, H18, C19,
 H21, C22, C2, H3, H7, H19, C20, H22, C1, C23, N3, H1A, H1B, N5, H23A, H23B,
 C44, C45, C24, C30, C43, N4, O3, C25, C29, N6, O2, C40, C42, H43, C38, C26,
 C28, H29, C31, H40, C41, H42, C35, H38A, H38B, H26, C27, H28, H31A, H31B, C32,
 H41, C34, C37, H27, C33, C36, H34, H37, H33, H36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.006
3. Others
 Fixed Sof: Cl(0.5) Cl1(0.5) C46(0.5) H46A(0.5) H46B(0.5) Cl00(0.5) Cl01(0.5)
 C47(0.5) H47A(0.5) H47B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C1(H1A,H1B), C8(H8A,H8B), C16(H16A,H16B),
 C23(H23A,H23B), C31(H31A,H31B), C38(H38A,H38B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29),
  C33(H33), C34(H34), C36(H36), C37(H37), C40(H40), C41(H41), C42(H42), C43(H43)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.2763(4) -0.0416(3) 0.9681(3) 0.1866(15) Uani 0.5 1 d . . P . .
Cl1 Cl 0.1402(3) -0.0429(2) 0.8303(2) 0.1373(9) Uani 0.5 1 d . . P . .
C46 C 0.2062(8) 0.0216(6) 0.8901(6) 0.094(3) Uani 0.5 1 d . . P . .
H46A H 0.258272 0.068877 0.838251 0.113 Uiso 0.5 1 calc R U P . .
H46B H 0.148453 0.064716 0.926047 0.113 Uiso 0.5 1 calc R U P . .
Cl00 Cl 0.4329(2) 0.94721(17) 0.19877(19) 0.1123(9) Uani 0.5 1 d . . P . .
Cl01 Cl 0.47969(18) 0.77272(15) 0.10508(14) 0.0836(6) Uani 0.5 1 d . . P . .
C47 C 0.3818(6) 0.8351(5) 0.1852(5) 0.063(2) Uani 0.5 1 d . . P . .
H47A H 0.360666 0.788132 0.251083 0.076 Uiso 0.5 1 calc R U P . .
H47B H 0.313657 0.852528 0.159529 0.076 Uiso 0.5 1 calc R U P . .
O1 O -0.1049(2) 0.6574(2) 0.5665(2) 0.0935(9) Uani 1 1 d . . . . .
O2 O 0.4868(2) 0.4579(2) 0.12572(18) 0.0871(7) Uani 1 1 d . . . . .
O3 O 0.2738(2) 0.2238(2) 0.74294(19) 0.0840(8) Uani 1 1 d . . . . .
N1 N -0.0061(2) 0.7826(2) 0.4339(2) 0.0756(7) Uani 1 1 d . . . . .
N2 N 0.0146(2) 0.7770(2) 0.5852(2) 0.0701(6) Uani 1 1 d . . . . .
N3 N 0.3912(2) 0.3659(2) 0.71225(19) 0.0624(6) Uani 1 1 d . . . . .
N4 N 0.4462(2) 0.2453(2) 0.6201(2) 0.0670(6) Uani 1 1 d . . . . .
N5 N 0.3150(2) 0.4745(2) 0.0804(2) 0.0691(7) Uani 1 1 d . . . . .
N6 N 0.3919(2) 0.3158(2) 0.1184(2) 0.0715(6) Uani 1 1 d . . . . .
C1 C 0.3307(3) 0.4126(3) 0.7959(2) 0.0679(8) Uani 1 1 d . . . . .
H1A H 0.386280 0.439845 0.822083 0.081 Uiso 1 1 calc R U . . .
H1B H 0.290612 0.358261 0.849578 0.081 Uiso 1 1 calc R U . . .
C2 C 0.2463(3) 0.4994(3) 0.7706(2) 0.0625(7) Uani 1 1 d . . . . .
C3 C 0.1436(3) 0.4760(3) 0.7525(3) 0.0704(9) Uani 1 1 d . . . . .
H3 H 0.128420 0.406883 0.755722 0.085 Uiso 1 1 calc R U . . .
C4 C 0.0660(3) 0.5542(3) 0.7302(3) 0.0755(10) Uani 1 1 d . . . . .
H4 H -0.001954 0.537758 0.718769 0.091 Uiso 1 1 calc R U . . .
C5 C 0.0870(3) 0.6585(3) 0.7244(2) 0.0671(7) Uani 1 1 d . . . . .
C6 C 0.1877(3) 0.6803(3) 0.7423(3) 0.0755(9) Uani 1 1 d . . . . .
H6 H 0.203056 0.749472 0.738306 0.091 Uiso 1 1 calc R U . . .
C7 C 0.2663(3) 0.6024(3) 0.7661(3) 0.0704(9) Uani 1 1 d . . . . .
H7 H 0.333274 0.619157 0.779182 0.084 Uiso 1 1 calc R U . . .
C8 C 0.0006(3) 0.7438(3) 0.6961(3) 0.0831(10) Uani 1 1 d . . . . .
H8A H -0.075815 0.718480 0.727062 0.100 Uiso 1 1 calc R U . . .
H8B H 0.008716 0.803899 0.723014 0.100 Uiso 1 1 calc R U . . .
C9 C -0.0411(3) 0.7314(3) 0.5324(3) 0.0739(7) Uani 1 1 d . . . . .
C10 C 0.0800(3) 0.8573(3) 0.5230(3) 0.0712(7) Uani 1 1 d . . . . .
C11 C 0.1465(3) 0.9263(3) 0.5396(3) 0.0878(9) Uani 1 1 d . . . . .
H11 H 0.157138 0.922432 0.603993 0.105 Uiso 1 1 calc R U . . .
C12 C 0.1980(4) 1.0024(3) 0.4585(4) 0.1022(11) Uani 1 1 d . . . . .
H12 H 0.242782 1.050683 0.469291 0.123 Uiso 1 1 calc R U . . .
C13 C 0.1849(4) 1.0087(4) 0.3621(4) 0.1090(9) Uani 1 1 d . . . . .
H13 H 0.220702 1.060703 0.308898 0.131 Uiso 1 1 calc R U . . .
C14 C 0.1185(3) 0.9377(3) 0.3444(3) 0.0931(10) Uani 1 1 d . . . . .
H14 H 0.108489 0.941428 0.279826 0.112 Uiso 1 1 calc R U . . .
C15 C 0.0671(3) 0.8604(3) 0.4266(3) 0.0735(7) Uani 1 1 d . . . . .
C16 C -0.0466(3) 0.7595(4) 0.3531(3) 0.0896(10) Uani 1 1 d . . . . .
H16A H -0.080338 0.822958 0.319131 0.108 Uiso 1 1 calc R U . . .
H16B H -0.106228 0.708912 0.381943 0.108 Uiso 1 1 calc R U . . .
C17 C 0.0458(3) 0.7163(3) 0.2753(3) 0.0707(8) Uani 1 1 d . . . . .
C18 C 0.1191(3) 0.6371(3) 0.3059(3) 0.0835(10) Uani 1 1 d . . . . .
H18 H 0.114081 0.612114 0.374691 0.100 Uiso 1 1 calc R U . . .
C19 C 0.1999(3) 0.5939(3) 0.2365(3) 0.0829(11) Uani 1 1 d . . . . .
H19 H 0.248523 0.539676 0.258720 0.100 Uiso 1 1 calc R U . . .
C20 C 0.2095(3) 0.6302(3) 0.1343(3) 0.0673(8) Uani 1 1 d . . . . .
C21 C 0.0541(3) 0.7512(3) 0.1752(3) 0.0825(11) Uani 1 1 d . . . . .
H21 H 0.003780 0.804371 0.153931 0.099 Uiso 1 1 calc R U . . .
C22 C 0.1367(3) 0.7097(3) 0.1021(3) 0.0822(10) Uani 1 1 d . . . . .
H22 H 0.141964 0.735529 0.033373 0.099 Uiso 1 1 calc R U . . .
C23 C 0.3011(4) 0.5863(3) 0.0566(3) 0.0820(11) Uani 1 1 d . . . . .
H23A H 0.282215 0.607594 -0.008721 0.098 Uiso 1 1 calc R U . . .
H23B H 0.373283 0.616649 0.050736 0.098 Uiso 1 1 calc R U . . .
C24 C 0.2424(3) 0.4040(3) 0.0685(2) 0.0680(7) Uani 1 1 d . . . . .
C25 C 0.2926(3) 0.3018(3) 0.0926(2) 0.0681(7) Uani 1 1 d . . . . .
C26 C 0.2412(3) 0.2175(3) 0.0857(3) 0.0896(9) Uani 1 1 d . . . . .
H26 H 0.272915 0.150243 0.101218 0.108 Uiso 1 1 calc R U . . .
C27 C 0.1397(4) 0.2343(4) 0.0548(3) 0.1025(10) Uani 1 1 d . . . . .
H27 H 0.104187 0.176860 0.048867 0.123 Uiso 1 1 calc R U . . .
C28 C 0.0911(4) 0.3289(4) 0.0334(3) 0.1008(11) Uani 1 1 d . . . . .
H28 H 0.021830 0.335518 0.014798 0.121 Uiso 1 1 calc R U . . .
C29 C 0.1419(3) 0.4193(4) 0.0380(3) 0.0884(8) Uani 1 1 d . . . . .
H29 H 0.109046 0.485844 0.021351 0.106 Uiso 1 1 calc R U . . .
C30 C 0.4070(3) 0.4196(3) 0.1089(2) 0.0666(7) Uani 1 1 d . . . . .
C31 C 0.4701(3) 0.2341(3) 0.1533(3) 0.0800(10) Uani 1 1 d . . . . .
H31A H 0.547713 0.253558 0.118045 0.096 Uiso 1 1 calc R U . . .
H31B H 0.456201 0.169897 0.135704 0.096 Uiso 1 1 calc R U . . .
C32 C 0.4600(3) 0.2136(3) 0.2662(3) 0.0663(8) Uani 1 1 d . . . . .
C33 C 0.5441(3) 0.1525(3) 0.3034(3) 0.0797(9) Uani 1 1 d . . . . .
H33 H 0.604838 0.125984 0.259103 0.096 Uiso 1 1 calc R U . . .
C34 C 0.5398(3) 0.1295(3) 0.4073(3) 0.0777(10) Uani 1 1 d . . . . .
H34 H 0.596710 0.086893 0.431746 0.093 Uiso 1 1 calc R U . . .
C35 C 0.4510(3) 0.1702(3) 0.4735(3) 0.0645(7) Uani 1 1 d . . . . .
C36 C 0.3711(3) 0.2514(3) 0.3341(3) 0.0696(9) Uani 1 1 d . . . . .
H36 H 0.311617 0.290884 0.311014 0.084 Uiso 1 1 calc R U . . .
C37 C 0.3694(3) 0.2317(3) 0.4347(3) 0.0691(9) Uani 1 1 d . . . . .
H37 H 0.310386 0.261235 0.478203 0.083 Uiso 1 1 calc R U . . .
C38 C 0.4504(4) 0.1517(3) 0.5835(3) 0.0766(10) Uani 1 1 d . . . . .
H38A H 0.384757 0.110867 0.622774 0.092 Uiso 1 1 calc R U . . .
H38B H 0.518495 0.110538 0.594602 0.092 Uiso 1 1 calc R U . . .
C39 C 0.5318(3) 0.3208(3) 0.5885(2) 0.0631(7) Uani 1 1 d . . . . .
C40 C 0.6328(3) 0.3251(3) 0.5204(3) 0.0785(9) Uani 1 1 d . . . . .
H40 H 0.657958 0.272705 0.484060 0.094 Uiso 1 1 calc R U . . .
C41 C 0.6978(3) 0.4108(3) 0.5065(3) 0.0846(9) Uani 1 1 d . . . . .
H41 H 0.767605 0.416701 0.458911 0.102 Uiso 1 1 calc R U . . .
C42 C 0.6623(3) 0.4869(3) 0.5605(3) 0.0817(9) Uani 1 1 d . . . . .
H42 H 0.708493 0.543407 0.549078 0.098 Uiso 1 1 calc R U . . .
C43 C 0.5575(3) 0.4820(3) 0.6334(3) 0.0710(9) Uani 1 1 d . . . . .
H43 H 0.532469 0.534359 0.669799 0.085 Uiso 1 1 calc R U . . .
C44 C 0.4940(3) 0.3957(3) 0.6479(2) 0.0605(7) Uani 1 1 d . . . . .
C45 C 0.3601(3) 0.2731(3) 0.6981(2) 0.0649(7) 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
Cl C46 1.589(9) . ?
Cl1 C46 1.683(10) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
Cl00 C47 1.713(8) . ?
Cl01 C47 1.700(7) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
O1 C9 1.228(4) . ?
O2 C30 1.224(5) . ?
O3 C45 1.228(4) . ?
N1 C9 1.362(4) . ?
N1 C15 1.382(5) . ?
N1 C16 1.439(5) . ?
N2 C8 1.480(5) . ?
N2 C9 1.372(5) . ?
N2 C10 1.370(4) . ?
N3 C1 1.444(4) . ?
N3 C44 1.368(4) . ?
N3 C45 1.376(5) . ?
N4 C38 1.426(5) . ?
N4 C39 1.416(4) . ?
N4 C45 1.394(4) . ?
N5 C23 1.433(5) . ?
N5 C24 1.396(5) . ?
N5 C30 1.364(5) . ?
N6 C25 1.378(5) . ?
N6 C30 1.363(5) . ?
N6 C31 1.447(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.501(5) . ?
C2 C3 1.403(5) . ?
C2 C7 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(5) . ?
C5 C6 1.371(5) . ?
C5 C8 1.515(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.359(6) . ?
C10 C15 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.517(5) . ?
C17 C18 1.367(5) . ?
C17 C21 1.348(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(5) . ?
C20 C22 1.373(5) . ?
C20 C23 1.514(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.404(5) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.424(5) . ?
C24 C29 1.372(5) . ?
C25 C26 1.352(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.327(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.407(7) . ?
C29 H29 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.512(5) . ?
C32 C33 1.370(5) . ?
C32 C36 1.379(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.401(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.381(5) . ?
C35 C37 1.359(5) . ?
C35 C38 1.498(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.364(5) . ?
C37 H37 0.9300 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.342(5) . ?
C39 C44 1.399(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.380(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.360(6) . ?
C42 H42 0.9300 . ?
C42 C43 1.407(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.375(5) . ?

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
Cl C46 Cl1 120.2(5) . . ?
Cl C46 H46A 107.3 . . ?
Cl C46 H46B 107.3 . . ?
Cl1 C46 H46A 107.3 . . ?
Cl1 C46 H46B 107.3 . . ?
H46A C46 H46B 106.9 . . ?
Cl00 C47 H47A 109.2 . . ?
Cl00 C47 H47B 109.2 . . ?
Cl01 C47 Cl00 112.2(4) . . ?
Cl01 C47 H47A 109.2 . . ?
Cl01 C47 H47B 109.2 . . ?
H47A C47 H47B 107.9 . . ?
C9 N1 C15 109.9(3) . . ?
C9 N1 C16 123.1(3) . . ?
C15 N1 C16 127.0(3) . . ?
C9 N2 C8 122.9(3) . . ?
C10 N2 C8 125.5(3) . . ?
C10 N2 C9 111.6(3) . . ?
C44 N3 C1 126.1(3) . . ?
C44 N3 C45 110.6(3) . . ?
C45 N3 C1 122.5(3) . . ?
C39 N4 C38 125.9(3) . . ?
C45 N4 C38 124.9(3) . . ?
C45 N4 C39 109.2(3) . . ?
C24 N5 C23 125.5(3) . . ?
C30 N5 C23 125.6(3) . . ?
C30 N5 C24 108.6(3) . . ?
C25 N6 C31 126.4(3) . . ?
C30 N6 C25 110.5(3) . . ?
C30 N6 C31 123.1(3) . . ?
N3 C1 H1A 108.5 . . ?
N3 C1 H1B 108.5 . . ?
N3 C1 C2 115.0(3) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C3 C2 C1 119.8(3) . . ?
C7 C2 C1 121.4(3) . . ?
C7 C2 C3 118.8(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C8 119.6(4) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C8 122.2(4) . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.7(4) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
N2 C8 C5 112.5(3) . . ?
N2 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C5 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 N1 127.6(4) . . ?
O1 C9 N2 127.0(4) . . ?
N1 C9 N2 105.3(3) . . ?
N2 C10 C15 105.5(3) . . ?
C11 C10 N2 133.5(4) . . ?
C11 C10 C15 121.0(3) . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.5(4) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 121.0 . . ?
C13 C14 C15 118.0(4) . . ?
C15 C14 H14 121.0 . . ?
N1 C15 C10 107.8(3) . . ?
N1 C15 C14 131.5(4) . . ?
C10 C15 C14 120.6(4) . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
N1 C16 C17 113.8(3) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C17 C16 120.2(3) . . ?
C21 C17 C16 121.1(3) . . ?
C21 C17 C18 118.7(3) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.9(4) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C23 121.2(3) . . ?
C22 C20 C19 119.3(3) . . ?
C22 C20 C23 119.4(3) . . ?
C17 C21 H21 119.1 . . ?
C17 C21 C22 121.9(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C22 C21 118.6(4) . . ?
C20 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
N5 C23 C20 113.9(3) . . ?
N5 C23 H23A 108.8 . . ?
N5 C23 H23B 108.8 . . ?
C20 C23 H23A 108.8 . . ?
C20 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
N5 C24 C25 107.1(3) . . ?
C29 C24 N5 131.6(4) . . ?
C29 C24 C25 121.3(4) . . ?
N6 C25 C24 105.7(3) . . ?
C26 C25 N6 134.3(4) . . ?
C26 C25 C24 120.0(4) . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 117.9(4) . . ?
C27 C26 H26 121.0 . . ?
C26 C27 H27 118.6 . . ?
C28 C27 C26 122.7(5) . . ?
C28 C27 H27 118.6 . . ?
C27 C28 H28 119.2 . . ?
C27 C28 C29 121.6(4) . . ?
C29 C28 H28 119.2 . . ?
C24 C29 C28 116.4(4) . . ?
C24 C29 H29 121.8 . . ?
C28 C29 H29 121.8 . . ?
O2 C30 N5 125.4(4) . . ?
O2 C30 N6 126.5(3) . . ?
N6 C30 N5 108.0(3) . . ?
N6 C31 H31A 108.8 . . ?
N6 C31 H31B 108.8 . . ?
N6 C31 C32 113.7(3) . . ?
H31A C31 H31B 107.7 . . ?
C32 C31 H31A 108.8 . . ?
C32 C31 H31B 108.8 . . ?
C33 C32 C31 117.8(3) . . ?
C33 C32 C36 117.9(3) . . ?
C36 C32 C31 124.3(3) . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.9(3) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(4) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C38 120.1(3) . . ?
C37 C35 C34 118.2(3) . . ?
C37 C35 C38 121.7(3) . . ?
C32 C36 H36 119.5 . . ?
C37 C36 C32 120.9(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C37 C36 122.1(3) . . ?
C35 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
N4 C38 C35 114.0(3) . . ?
N4 C38 H38A 108.7 . . ?
N4 C38 H38B 108.8 . . ?
C35 C38 H38A 108.7 . . ?
C35 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C40 C39 N4 131.2(4) . . ?
C40 C39 C44 122.8(4) . . ?
C44 C39 N4 105.9(3) . . ?
C39 C40 H40 121.4 . . ?
C39 C40 C41 117.1(4) . . ?
C41 C40 H40 121.4 . . ?
C40 C41 H41 119.2 . . ?
C42 C41 C40 121.7(4) . . ?
C42 C41 H41 119.2 . . ?
C41 C42 H42 119.2 . . ?
C41 C42 C43 121.6(4) . . ?
C43 C42 H42 119.2 . . ?
C42 C43 H43 121.8 . . ?
C44 C43 C42 116.4(4) . . ?
C44 C43 H43 121.8 . . ?
N3 C44 C39 108.2(3) . . ?
N3 C44 C43 131.5(3) . . ?
C43 C44 C39 120.3(3) . . ?
O3 C45 N3 128.1(3) . . ?
O3 C45 N4 125.7(3) . . ?
N3 C45 N4 106.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C16 C17 C18 47.7(5) . . . . ?
N1 C16 C17 C21 -135.5(4) . . . . ?
N2 C10 C11 C12 -177.0(4) . . . . ?
N2 C10 C15 N1 0.5(4) . . . . ?
N2 C10 C15 C14 176.7(3) . . . . ?
N3 C1 C2 C3 72.2(4) . . . . ?
N3 C1 C2 C7 -108.8(4) . . . . ?
N4 C39 C40 C41 179.9(4) . . . . ?
N4 C39 C44 N3 0.3(4) . . . . ?
N4 C39 C44 C43 -178.2(3) . . . . ?
N5 C24 C25 N6 0.5(3) . . . . ?
N5 C24 C25 C26 -178.8(3) . . . . ?
N5 C24 C29 C28 179.2(3) . . . . ?
N6 C25 C26 C27 -178.9(4) . . . . ?
N6 C31 C32 C33 -167.8(3) . . . . ?
N6 C31 C32 C36 12.8(5) . . . . ?
C1 N3 C44 C39 170.5(3) . . . . ?
C1 N3 C44 C43 -11.2(6) . . . . ?
C1 N3 C45 O3 9.3(6) . . . . ?
C1 N3 C45 N4 -171.6(3) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C7 C6 179.7(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 C8 178.0(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C4 C5 C8 N2 -83.5(4) . . . . ?
C5 C6 C7 C2 1.2(5) . . . . ?
C6 C5 C8 N2 94.9(4) . . . . ?
C7 C2 C3 C4 0.5(5) . . . . ?
C8 N2 C9 O1 -2.5(6) . . . . ?
C8 N2 C9 N1 -179.8(3) . . . . ?
C8 N2 C10 C11 -0.2(6) . . . . ?
C8 N2 C10 C15 -179.6(3) . . . . ?
C8 C5 C6 C7 -178.8(3) . . . . ?
C9 N1 C15 C10 0.8(4) . . . . ?
C9 N1 C15 C14 -174.9(4) . . . . ?
C9 N1 C16 C17 -115.5(4) . . . . ?
C9 N2 C8 C5 90.4(4) . . . . ?
C9 N2 C10 C11 177.8(4) . . . . ?
C9 N2 C10 C15 -1.6(4) . . . . ?
C10 N2 C8 C5 -91.7(4) . . . . ?
C10 N2 C9 O1 179.3(4) . . . . ?
C10 N2 C9 N1 2.0(4) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C10 C15 N1 -179.0(3) . . . . ?
C11 C10 C15 C14 -2.8(6) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 C15 -0.5(6) . . . . ?
C13 C14 C15 N1 177.1(4) . . . . ?
C13 C14 C15 C10 1.8(6) . . . . ?
C15 N1 C9 O1 -179.0(4) . . . . ?
C15 N1 C9 N2 -1.7(4) . . . . ?
C15 N1 C16 C17 67.8(5) . . . . ?
C15 C10 C11 C12 2.3(6) . . . . ?
C16 N1 C9 O1 3.8(6) . . . . ?
C16 N1 C9 N2 -178.9(3) . . . . ?
C16 N1 C15 C10 177.9(3) . . . . ?
C16 N1 C15 C14 2.1(6) . . . . ?
C16 C17 C18 C19 177.1(4) . . . . ?
C16 C17 C21 C22 -177.8(4) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C17 C21 C22 C20 1.0(6) . . . . ?
C18 C17 C21 C22 -0.9(6) . . . . ?
C18 C19 C20 C22 -0.5(6) . . . . ?
C18 C19 C20 C23 177.6(4) . . . . ?
C19 C20 C22 C21 -0.2(6) . . . . ?
C19 C20 C23 N5 43.7(6) . . . . ?
C21 C17 C18 C19 0.2(6) . . . . ?
C22 C20 C23 N5 -138.1(4) . . . . ?
C23 N5 C24 C25 175.1(3) . . . . ?
C23 N5 C24 C29 -3.5(6) . . . . ?
C23 N5 C30 O2 5.8(5) . . . . ?
C23 N5 C30 N6 -176.1(3) . . . . ?
C23 C20 C22 C21 -178.4(4) . . . . ?
C24 N5 C23 C20 76.7(5) . . . . ?
C24 N5 C30 O2 -180.0(3) . . . . ?
C24 N5 C30 N6 -1.9(3) . . . . ?
C24 C25 C26 C27 0.0(5) . . . . ?
C25 N6 C30 O2 -179.7(3) . . . . ?
C25 N6 C30 N5 2.3(4) . . . . ?
C25 N6 C31 C32 -103.4(4) . . . . ?
C25 C24 C29 C28 0.8(5) . . . . ?
C25 C26 C27 C28 -0.9(6) . . . . ?
C26 C27 C28 C29 1.8(6) . . . . ?
C27 C28 C29 C24 -1.7(6) . . . . ?
C29 C24 C25 N6 179.2(3) . . . . ?
C29 C24 C25 C26 0.0(5) . . . . ?
C30 N5 C23 C20 -110.1(4) . . . . ?
C30 N5 C24 C25 0.9(3) . . . . ?
C30 N5 C24 C29 -177.6(3) . . . . ?
C30 N6 C25 C24 -1.7(3) . . . . ?
C30 N6 C25 C26 177.4(4) . . . . ?
C30 N6 C31 C32 75.0(4) . . . . ?
C31 N6 C25 C24 176.9(3) . . . . ?
C31 N6 C25 C26 -4.0(6) . . . . ?
C31 N6 C30 O2 1.6(5) . . . . ?
C31 N6 C30 N5 -176.4(3) . . . . ?
C31 C32 C33 C34 -179.5(4) . . . . ?
C31 C32 C36 C37 -178.3(4) . . . . ?
C32 C33 C34 C35 -1.2(6) . . . . ?
C32 C36 C37 C35 -3.3(6) . . . . ?
C33 C32 C36 C37 2.3(6) . . . . ?
C33 C34 C35 C37 0.3(6) . . . . ?
C33 C34 C35 C38 -175.9(4) . . . . ?
C34 C35 C37 C36 1.9(6) . . . . ?
C34 C35 C38 N4 122.0(4) . . . . ?
C36 C32 C33 C34 -0.1(6) . . . . ?
C37 C35 C38 N4 -54.1(5) . . . . ?
C38 N4 C39 C40 0.2(6) . . . . ?
C38 N4 C39 C44 -177.1(3) . . . . ?
C38 N4 C45 O3 -3.4(6) . . . . ?
C38 N4 C45 N3 177.5(3) . . . . ?
C38 C35 C37 C36 178.1(3) . . . . ?
C39 N4 C38 C35 -64.4(5) . . . . ?
C39 N4 C45 O3 -179.4(3) . . . . ?
C39 N4 C45 N3 1.5(4) . . . . ?
C39 C40 C41 C42 1.1(6) . . . . ?
C40 C39 C44 N3 -177.2(3) . . . . ?
C40 C39 C44 C43 4.3(5) . . . . ?
C40 C41 C42 C43 0.0(6) . . . . ?
C41 C42 C43 C44 1.0(6) . . . . ?
C42 C43 C44 N3 178.9(4) . . . . ?
C42 C43 C44 C39 -3.0(5) . . . . ?
C44 N3 C1 C2 91.9(4) . . . . ?
C44 N3 C45 O3 179.6(4) . . . . ?
C44 N3 C45 N4 -1.3(4) . . . . ?
C44 C39 C40 C41 -3.3(6) . . . . ?
C45 N3 C1 C2 -99.3(4) . . . . ?
C45 N3 C44 C39 0.6(4) . . . . ?
C45 N3 C44 C43 178.9(4) . . . . ?
C45 N4 C38 C35 120.3(4) . . . . ?
C45 N4 C39 C40 176.1(4) . . . . ?
C45 N4 C39 C44 -1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT084_11_a                
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: We tried many times to obtain the high-quanlity crystals, 
but failed. In the crystal, it is thin and the high anlge of diffraction 
is weak, thus the wR2 value is beyond 0.36. 
However, the structure can be clearly determined. 
;

# end Validation Reply Form
