# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

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

data_3v
_database_code_depnum_ccdc_archive 'CCDC 2178229'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-10-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 Cl N O'
_chemical_formula_sum            'C23 H16 Cl N O'
_chemical_formula_weight         357.82
_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                   6.1239(8)
_cell_length_b                   17.725(3)
_cell_length_c                   18.644(3)
_cell_angle_alpha                65.607(6)
_cell_angle_beta                 80.571(5)
_cell_angle_gamma                89.902(5)
_cell_volume                     1813.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7659
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.429
_cell_measurement_theta_min      2.304
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1944 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.3378.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28020
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.092
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4704
_reflns_number_total             6349
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0797
_refine_ls_restrained_S_all      1.015
_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)+(0.1376P)²+0.2638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C18(H18), C28(H28), C39(H39)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25),
  C26(H26), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C41(H41), C43(H43), C44(H44), C45(H45), C46(H46)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80164(15) 0.62176(6) 1.05478(5) 0.0384(3) Uani 1 1 d . . . . .
Cl2 Cl -0.35627(14) 1.12173(6) 1.05481(5) 0.0383(3) Uani 1 1 d . . . . .
O1 O 1.1479(4) 0.55146(16) 0.72143(15) 0.0378(6) Uani 1 1 d . . . . .
O2 O -0.3689(4) 1.05133(16) 0.72155(15) 0.0373(6) Uani 1 1 d . . . . .
N1 N 0.5713(5) 0.71085(18) 0.66339(19) 0.0373(7) Uani 1 1 d . . . . .
N2 N 0.2653(5) 1.21059(18) 0.66307(19) 0.0366(7) Uani 1 1 d . . . . .
C1 C 0.4500(6) 0.6503(2) 0.9795(2) 0.0300(8) Uani 1 1 d . . . . .
H1 H 0.3903 0.6759 1.0135 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3359(5) 0.64599(19) 0.9223(2) 0.0281(7) Uani 1 1 d . . . . .
H2 H 0.1958 0.6688 0.9175 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4230(5) 0.60910(19) 0.8726(2) 0.0251(7) Uani 1 1 d . . . . .
H3 H 0.3426 0.6070 0.8339 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6281(5) 0.57495(18) 0.87878(19) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.7351(5) 0.53594(18) 0.82672(19) 0.0230(7) Uani 1 1 d . . . . .
H5 H 0.8642 0.5044 0.8467 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7671(5) 0.57768(18) 0.73533(19) 0.0219(7) Uani 1 1 d . . . . .
C7 C 0.9884(5) 0.57183(19) 0.6880(2) 0.0258(7) Uani 1 1 d . . . . .
C8 C 1.0006(5) 0.5917(2) 0.6030(2) 0.0275(7) Uani 1 1 d . . . . .
C9 C 1.2011(6) 0.6254(2) 0.5496(2) 0.0388(9) Uani 1 1 d . . . . .
H9 H 1.3272 0.6357 0.5688 0.047 Uiso 1 1 calc R U . . .
C10 C 1.2168(7) 0.6438(3) 0.4694(3) 0.0508(11) Uani 1 1 d . . . . .
H10 H 1.3518 0.6680 0.4332 0.061 Uiso 1 1 calc R U . . .
C11 C 1.0352(7) 0.6269(3) 0.4423(2) 0.0501(11) Uani 1 1 d . . . . .
H11 H 1.0463 0.6391 0.3872 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7131(6) 0.2681(2) 0.7670(2) 0.0359(9) Uani 1 1 d . . . . .
H12 H 0.7321 0.2168 0.7628 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8664(6) 0.2982(2) 0.7972(2) 0.0332(8) Uani 1 1 d . . . . .
H13 H 0.9916 0.2681 0.8130 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8363(5) 0.37309(19) 0.8043(2) 0.0270(7) Uani 1 1 d . . . . .
H14 H 0.9406 0.3935 0.8258 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6547(5) 0.41804(18) 0.78025(18) 0.0227(7) Uani 1 1 d . . . . .
C16 C 0.5036(5) 0.3864(2) 0.7497(2) 0.0279(7) Uani 1 1 d . . . . .
H16 H 0.3784 0.4161 0.7332 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5343(6) 0.3115(2) 0.7432(2) 0.0342(8) Uani 1 1 d . . . . .
H17 H 0.4303 0.2906 0.7220 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6103(5) 0.49763(18) 0.78623(19) 0.0220(7) Uani 1 1 d . . . . .
H18 H 0.4495 0.5085 0.7907 0.026 Uiso 1 1 calc R U . . .
C19 C 0.8350(7) 0.5920(3) 0.4946(2) 0.0433(9) Uani 1 1 d . . . . .
H19 H 0.7118 0.5795 0.4753 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8175(6) 0.5759(2) 0.5742(2) 0.0338(8) Uani 1 1 d . . . . .
H20 H 0.6801 0.5539 0.6097 0.041 Uiso 1 1 calc R U . . .
C21 C 0.6517(5) 0.61616(19) 0.98515(19) 0.0264(7) Uani 1 1 d . . . . .
C22 C 0.7416(5) 0.57865(18) 0.93599(19) 0.0243(7) Uani 1 1 d . . . . .
H22 H 0.8812 0.5554 0.9415 0.029 Uiso 1 1 calc R U . . .
C23 C 0.6573(5) 0.6520(2) 0.6955(2) 0.0262(7) Uani 1 1 d . . . . .
C24 C 0.0706(5) 1.1501(2) 0.9794(2) 0.0289(8) Uani 1 1 d . . . . .
H24 H 0.0962 1.1757 1.0133 0.035 Uiso 1 1 calc R U . . .
C25 C 0.2419(5) 1.14575(19) 0.9222(2) 0.0275(7) Uani 1 1 d . . . . .
H25 H 0.3867 1.1684 0.9175 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2052(5) 1.10929(19) 0.8728(2) 0.0253(7) Uani 1 1 d . . . . .
H26 H 0.3243 1.1072 0.8341 0.030 Uiso 1 1 calc R U . . .
C27 C -0.0071(5) 1.07503(18) 0.87882(19) 0.0226(7) Uani 1 1 d . . . . .
C28 C -0.0613(5) 1.03602(18) 0.82652(19) 0.0234(7) Uani 1 1 d . . . . .
H28 H -0.2103 1.0046 0.8463 0.028 Uiso 1 1 calc R U . . .
C29 C -0.0015(5) 1.07767(18) 0.73506(19) 0.0218(7) Uani 1 1 d . . . . .
C30 C -0.1761(5) 1.07193(19) 0.6877(2) 0.0264(7) Uani 1 1 d . . . . .
C31 C -0.1031(5) 1.09211(19) 0.6026(2) 0.0281(7) Uani 1 1 d . . . . .
C32 C 0.1079(6) 1.0763(2) 0.5737(2) 0.0360(8) Uani 1 1 d . . . . .
H32 H 0.2102 1.0545 0.6092 0.043 Uiso 1 1 calc R U . . .
C33 C 0.1704(7) 1.0920(3) 0.4939(2) 0.0437(9) Uani 1 1 d . . . . .
H33 H 0.3126 1.0791 0.4748 0.052 Uiso 1 1 calc R U . . .
C34 C 0.0228(7) 1.1267(3) 0.4419(2) 0.0501(11) Uani 1 1 d . . . . .
H34 H 0.0661 1.1392 0.3867 0.060 Uiso 1 1 calc R U . . .
C35 C 0.0196(6) 0.7680(2) 0.7666(2) 0.0336(8) Uani 1 1 d . . . . .
H35 H 0.0045 0.7170 0.7619 0.040 Uiso 1 1 calc R U . . .
C36 C 0.2235(6) 0.8120(2) 0.7428(2) 0.0333(8) Uani 1 1 d . . . . .
H36 H 0.3488 0.7913 0.7214 0.040 Uiso 1 1 calc R U . . .
C37 C 0.2469(5) 0.8868(2) 0.7497(2) 0.0275(7) Uani 1 1 d . . . . .
H37 H 0.3880 0.9166 0.7334 0.033 Uiso 1 1 calc R U . . .
C38 C 0.0649(5) 0.91744(18) 0.78032(18) 0.0221(7) Uani 1 1 d . . . . .
C39 C 0.1031(5) 0.99782(18) 0.78604(19) 0.0215(7) Uani 1 1 d . . . . .
H39 H 0.2593 1.0085 0.7907 0.026 Uiso 1 1 calc R U . . .
C40 C -0.1371(5) 1.11610(19) 0.98502(19) 0.0265(7) Uani 1 1 d . . . . .
C41 C -0.1768(5) 1.07898(18) 0.93616(19) 0.0247(7) Uani 1 1 d . . . . .
H41 H -0.3217 1.0558 0.9417 0.030 Uiso 1 1 calc R U . . .
C42 C 0.1461(5) 1.15171(19) 0.6957(2) 0.0249(7) Uani 1 1 d . . . . .
C43 C -0.1861(7) 1.1433(3) 0.4697(3) 0.0521(11) Uani 1 1 d . . . . .
H43 H -0.2858 1.1672 0.4337 0.062 Uiso 1 1 calc R U . . .
C44 C -0.2512(6) 1.1254(2) 0.5501(2) 0.0395(9) Uani 1 1 d . . . . .
H44 H -0.3964 1.1357 0.5694 0.047 Uiso 1 1 calc R U . . .
C45 C -0.1407(5) 0.8736(2) 0.8040(2) 0.0286(7) Uani 1 1 d . . . . .
H45 H -0.2664 0.8948 0.8246 0.034 Uiso 1 1 calc R U . . .
C46 C -0.1635(6) 0.7986(2) 0.7974(2) 0.0339(8) Uani 1 1 d . . . . .
H46 H -0.3043 0.7684 0.8141 0.041 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 C21 1.742(3) . ?
Cl2 C40 1.743(3) . ?
O1 C7 1.219(4) . ?
O2 C30 1.222(4) . ?
N1 C23 1.145(4) . ?
N2 C42 1.151(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(5) . ?
C1 C21 1.375(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C4 C5 1.481(4) . ?
C4 C22 1.388(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.529(4) . ?
C5 C18 1.493(4) . ?
C6 C7 1.519(4) . ?
C6 C18 1.559(4) . ?
C6 C23 1.446(5) . ?
C7 C8 1.464(5) . ?
C8 C9 1.403(5) . ?
C8 C20 1.396(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(6) . ?
C11 H11 0.9500 . ?
C11 C19 1.396(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(5) . ?
C12 C17 1.365(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.397(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(4) . ?
C15 C16 1.391(4) . ?
C15 C18 1.482(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(5) . ?
C17 H17 0.9500 . ?
C18 H18 1.0000 . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(5) . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.394(5) . ?
C24 C40 1.378(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.371(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.403(4) . ?
C27 C28 1.484(4) . ?
C27 C41 1.388(5) . ?
C28 H28 1.0000 . ?
C28 C29 1.531(4) . ?
C28 C39 1.487(4) . ?
C29 C30 1.522(4) . ?
C29 C39 1.550(4) . ?
C29 C42 1.439(4) . ?
C30 C31 1.465(5) . ?
C31 C32 1.391(5) . ?
C31 C44 1.393(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.383(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.388(6) . ?
C34 H34 0.9500 . ?
C34 C43 1.378(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.378(5) . ?
C35 C46 1.388(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.393(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.382(5) . ?
C38 C39 1.494(4) . ?
C38 C45 1.386(4) . ?
C39 H39 1.0000 . ?
C40 C41 1.375(5) . ?
C41 H41 0.9500 . ?
C43 H43 0.9500 . ?
C43 C44 1.384(6) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C45 C46 1.395(5) . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.1 . . ?
C21 C1 H1 121.1 . . ?
C21 C1 C2 117.8(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 123.8(3) . . ?
C22 C4 C3 118.6(3) . . ?
C22 C4 C5 117.6(3) . . ?
C4 C5 H5 112.8 . . ?
C4 C5 C6 123.4(3) . . ?
C4 C5 C18 123.8(3) . . ?
C6 C5 H5 112.8 . . ?
C18 C5 H5 112.8 . . ?
C18 C5 C6 62.1(2) . . ?
C5 C6 C18 57.8(2) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 C18 119.6(3) . . ?
C23 C6 C5 120.3(3) . . ?
C23 C6 C7 114.3(3) . . ?
C23 C6 C18 115.3(3) . . ?
O1 C7 C6 119.6(3) . . ?
O1 C7 C8 122.5(3) . . ?
C8 C7 C6 117.9(3) . . ?
C9 C8 C7 119.6(3) . . ?
C20 C8 C7 121.2(3) . . ?
C20 C8 C9 119.1(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C19 121.0(4) . . ?
C19 C11 H11 119.5 . . ?
C13 C12 H12 119.8 . . ?
C17 C12 H12 119.8 . . ?
C17 C12 C13 120.4(3) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C18 123.8(3) . . ?
C16 C15 C14 118.6(3) . . ?
C16 C15 C18 117.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C5 C18 C6 60.1(2) . . ?
C5 C18 H18 113.2 . . ?
C6 C18 H18 113.2 . . ?
C15 C18 C5 125.6(3) . . ?
C15 C18 C6 121.5(3) . . ?
C15 C18 H18 113.2 . . ?
C11 C19 H19 120.2 . . ?
C20 C19 C11 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C8 C20 H20 119.9 . . ?
C19 C20 C8 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C1 C21 Cl1 119.2(3) . . ?
C1 C21 C22 121.9(3) . . ?
C22 C21 Cl1 118.9(3) . . ?
C4 C22 H22 119.9 . . ?
C21 C22 C4 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
N1 C23 C6 179.4(4) . . ?
C25 C24 H24 121.0 . . ?
C40 C24 H24 121.0 . . ?
C40 C24 C25 117.9(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 123.7(3) . . ?
C41 C27 C26 118.2(3) . . ?
C41 C27 C28 118.1(3) . . ?
C27 C28 H28 112.8 . . ?
C27 C28 C29 123.5(3) . . ?
C27 C28 C39 124.1(3) . . ?
C29 C28 H28 112.8 . . ?
C39 C28 H28 112.8 . . ?
C39 C28 C29 61.8(2) . . ?
C28 C29 C39 57.7(2) . . ?
C30 C29 C28 117.8(3) . . ?
C30 C29 C39 119.5(2) . . ?
C42 C29 C28 120.3(3) . . ?
C42 C29 C30 114.4(3) . . ?
C42 C29 C39 115.8(3) . . ?
O2 C30 C29 119.3(3) . . ?
O2 C30 C31 123.0(3) . . ?
C31 C30 C29 117.7(3) . . ?
C32 C31 C30 121.4(3) . . ?
C32 C31 C44 119.5(4) . . ?
C44 C31 C30 119.1(3) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(4) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 120.4 . . ?
C32 C33 C34 119.2(4) . . ?
C34 C33 H33 120.4 . . ?
C33 C34 H34 119.7 . . ?
C43 C34 C33 120.6(4) . . ?
C43 C34 H34 119.7 . . ?
C36 C35 H35 120.1 . . ?
C36 C35 C46 119.7(3) . . ?
C46 C35 H35 120.1 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.4(3) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0(3) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C39 116.9(3) . . ?
C37 C38 C45 119.8(3) . . ?
C45 C38 C39 123.3(3) . . ?
C28 C39 C29 60.5(2) . . ?
C28 C39 C38 125.6(3) . . ?
C28 C39 H39 113.0 . . ?
C29 C39 H39 113.0 . . ?
C38 C39 C29 121.8(3) . . ?
C38 C39 H39 113.0 . . ?
C24 C40 Cl2 119.2(3) . . ?
C41 C40 Cl2 119.1(2) . . ?
C41 C40 C24 121.7(3) . . ?
C27 C41 H41 119.7 . . ?
C40 C41 C27 120.6(3) . . ?
C40 C41 H41 119.7 . . ?
N2 C42 C29 178.9(4) . . ?
C34 C43 H43 119.9 . . ?
C34 C43 C44 120.2(4) . . ?
C44 C43 H43 119.9 . . ?
C31 C44 H44 120.1 . . ?
C43 C44 C31 119.8(4) . . ?
C43 C44 H44 120.1 . . ?
C38 C45 H45 119.9 . . ?
C38 C45 C46 120.1(3) . . ?
C46 C45 H45 119.9 . . ?
C35 C46 C45 119.9(3) . . ?
C35 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C21 C22 C4 -178.6(2) . . . . ?
Cl2 C40 C41 C27 178.6(2) . . . . ?
O1 C7 C8 C9 -29.8(5) . . . . ?
O1 C7 C8 C20 148.6(3) . . . . ?
O2 C30 C31 C32 -148.4(3) . . . . ?
O2 C30 C31 C44 29.6(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C21 C22 C4 0.2(5) . . . . ?
C2 C1 C21 Cl1 179.0(2) . . . . ?
C2 C1 C21 C22 0.1(5) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
C2 C3 C4 C22 0.2(5) . . . . ?
C3 C4 C5 C6 50.7(4) . . . . ?
C3 C4 C5 C18 -25.8(5) . . . . ?
C3 C4 C22 C21 -0.4(4) . . . . ?
C4 C5 C6 C7 137.1(3) . . . . ?
C4 C5 C6 C18 -113.9(3) . . . . ?
C4 C5 C6 C23 -11.3(4) . . . . ?
C4 C5 C18 C6 113.3(3) . . . . ?
C4 C5 C18 C15 -137.4(3) . . . . ?
C5 C4 C22 C21 178.5(3) . . . . ?
C5 C6 C7 O1 -16.2(4) . . . . ?
C5 C6 C7 C8 164.2(3) . . . . ?
C5 C6 C18 C15 -115.8(3) . . . . ?
C6 C5 C18 C15 109.3(3) . . . . ?
C6 C7 C8 C9 149.8(3) . . . . ?
C6 C7 C8 C20 -31.7(4) . . . . ?
C7 C6 C18 C5 106.3(3) . . . . ?
C7 C6 C18 C15 -9.5(4) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C7 C8 C20 C19 -177.4(3) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C9 C8 C20 C19 1.1(5) . . . . ?
C9 C10 C11 C19 0.6(7) . . . . ?
C10 C11 C19 C20 1.3(7) . . . . ?
C11 C19 C20 C8 -2.1(6) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C13 C14 C15 C18 179.6(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C14 C15 C18 C5 -7.5(5) . . . . ?
C14 C15 C18 C6 66.3(4) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
C16 C15 C18 C5 171.6(3) . . . . ?
C16 C15 C18 C6 -114.6(3) . . . . ?
C17 C12 C13 C14 0.9(5) . . . . ?
C18 C5 C6 C7 -109.0(3) . . . . ?
C18 C5 C6 C23 102.5(3) . . . . ?
C18 C6 C7 O1 -83.1(4) . . . . ?
C18 C6 C7 C8 97.3(3) . . . . ?
C18 C15 C16 C17 -179.4(3) . . . . ?
C20 C8 C9 C10 0.9(5) . . . . ?
C21 C1 C2 C3 -0.3(5) . . . . ?
C22 C4 C5 C6 -128.2(3) . . . . ?
C22 C4 C5 C18 155.3(3) . . . . ?
C23 C6 C7 O1 134.1(3) . . . . ?
C23 C6 C7 C8 -45.5(4) . . . . ?
C23 C6 C18 C5 -111.3(3) . . . . ?
C23 C6 C18 C15 133.0(3) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C24 C40 C41 C27 -0.3(5) . . . . ?
C25 C24 C40 Cl2 -179.1(2) . . . . ?
C25 C24 C40 C41 -0.2(5) . . . . ?
C25 C26 C27 C28 178.8(3) . . . . ?
C25 C26 C27 C41 -0.2(4) . . . . ?
C26 C27 C28 C29 -50.6(4) . . . . ?
C26 C27 C28 C39 25.7(5) . . . . ?
C26 C27 C41 C40 0.5(4) . . . . ?
C27 C28 C29 C30 -137.0(3) . . . . ?
C27 C28 C29 C39 114.1(3) . . . . ?
C27 C28 C29 C42 11.0(4) . . . . ?
C27 C28 C39 C29 -113.1(3) . . . . ?
C27 C28 C39 C38 137.0(3) . . . . ?
C28 C27 C41 C40 -178.5(3) . . . . ?
C28 C29 C30 O2 15.8(4) . . . . ?
C28 C29 C30 C31 -164.5(3) . . . . ?
C28 C29 C39 C38 115.8(3) . . . . ?
C29 C28 C39 C38 -109.8(3) . . . . ?
C29 C30 C31 C32 32.0(4) . . . . ?
C29 C30 C31 C44 -150.1(3) . . . . ?
C30 C29 C39 C28 -106.0(3) . . . . ?
C30 C29 C39 C38 9.8(4) . . . . ?
C30 C31 C32 C33 176.8(3) . . . . ?
C30 C31 C44 C43 -178.8(3) . . . . ?
C31 C32 C33 C34 2.4(6) . . . . ?
C32 C31 C44 C43 -0.8(5) . . . . ?
C32 C33 C34 C43 -1.8(6) . . . . ?
C33 C34 C43 C44 -0.1(7) . . . . ?
C34 C43 C44 C31 1.4(6) . . . . ?
C35 C36 C37 C38 -0.3(5) . . . . ?
C36 C35 C46 C45 0.2(5) . . . . ?
C36 C37 C38 C39 179.9(3) . . . . ?
C36 C37 C38 C45 0.0(5) . . . . ?
C37 C38 C39 C28 -171.6(3) . . . . ?
C37 C38 C39 C29 114.0(3) . . . . ?
C37 C38 C45 C46 0.5(5) . . . . ?
C38 C45 C46 C35 -0.5(5) . . . . ?
C39 C28 C29 C30 109.0(3) . . . . ?
C39 C28 C29 C42 -103.1(3) . . . . ?
C39 C29 C30 O2 82.5(4) . . . . ?
C39 C29 C30 C31 -97.9(3) . . . . ?
C39 C38 C45 C46 -179.5(3) . . . . ?
C40 C24 C25 C26 0.4(5) . . . . ?
C41 C27 C28 C29 128.3(3) . . . . ?
C41 C27 C28 C39 -155.3(3) . . . . ?
C42 C29 C30 O2 -134.0(3) . . . . ?
C42 C29 C30 C31 45.7(4) . . . . ?
C42 C29 C39 C28 110.9(3) . . . . ?
C42 C29 C39 C38 -133.2(3) . . . . ?
C44 C31 C32 C33 -1.1(5) . . . . ?
C45 C38 C39 C28 8.4(5) . . . . ?
C45 C38 C39 C29 -66.0(4) . . . . ?
C46 C35 C36 C37 0.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
