# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_httmcn
_database_code_depnum_ccdc_archive 'CCDC 2325273'
loop_
_audit_author_name
_audit_author_address
lvkuo
;JILIN UNIVERSITY
China
;
_audit_update_record             
;
2024-01-13 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2024-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            TTM-1CN
_chemical_name_systematic        BnBTM
_chemical_formula_moiety         'C20 H6 Cl8 N1'
_chemical_formula_sum            'C20 H6 Cl8 N'
_chemical_formula_weight         543.86
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0305(9)
_cell_length_b                   8.0731(5)
_cell_length_c                   18.9296(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.608(2)
_cell_angle_gamma                90
_cell_volume                     2137.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47418
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.700
_diffrn_ambient_temperature      110.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4235
_reflns_number_total             4910
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+11.0585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1-C2
 1.53 with sigma of 0.02
 N1-C1
 1.158 with sigma of 0.02
 C18-C22
 1.53 with sigma of 0.02
 N3-C22
 1.158 with sigma of 0.02
 C21-C12
 1.53 with sigma of 0.01
 N2-C21
 1.158 with sigma of 0.02
 C2-Cl9 \\sim C2-C1
 with sigma of 0.02
 C1-C3 \\sim C1-C7
 with sigma of 0.02
 Cl5-C18 \\sim C22-C18
 with sigma of 0.02
 Cl5-N3 \\sim C22-N3
 with sigma of 0.02
 C22-C17 \\sim C22-C19
 with sigma of 0.02
 C21-C11 \\sim C21-C13
 with sigma of 0.02
 N1-C3 \\sim N1-C7
 with sigma of 0.02
 N2-C11 \\sim N2-C13
 with sigma of 0.02
 N3-C17 \\sim N3-C19
 with sigma of 0.02
3. Restrained planarity
 C1, N1, C2, C3, C7
 with sigma of 0.01
 C21, N2, C11, C12, C13
 with sigma of 0.01
 C22, N3, C19, C17, C18
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim C1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C22 \\sim N3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Cl8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C21 \\sim N2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C22) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C21) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
Uanis(C1) = Uanis(C22) = Uanis(C21)
Uanis(N2) = Uanis(N1) = Uanis(N3)
5. Others
 Fixed Sof: Cl8(0.66667) Cl5(0.66667) Cl9(0.66667) N1(0.33333) C1(0.33333)
 N3(0.33333) N2(0.33333) C22(0.33333) C21(0.33333)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C19(H19), C13(H13), C17(H17), C7(H7), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41810(7) 0.64735(13) 0.63367(5) 0.0309(2) Uani 1 1 d . . . . .
Cl4 Cl 0.25165(7) -0.02176(13) 0.57986(6) 0.0336(2) Uani 1 1 d . . . . .
Cl6 Cl 0.38893(8) 0.38126(14) 0.46908(6) 0.0358(2) Uani 1 1 d . . . . .
Cl3 Cl 0.16663(8) 0.62158(13) 0.51452(6) 0.0358(2) Uani 1 1 d . . . . .
Cl7 Cl 0.35809(8) 0.19601(15) 0.74297(6) 0.0373(3) Uani 1 1 d . . . . .
Cl2 Cl 0.09384(9) 0.30035(17) 0.67666(7) 0.0494(3) Uani 1 1 d . . . . .
Cl8 Cl 0.66351(11) 0.0199(2) 0.60633(10) 0.0309(4) Uani 0.6667 1 d . U P A 1
Cl5 Cl -0.01216(13) 0.1238(3) 0.37009(10) 0.0355(4) Uani 0.6667 1 d D . P B 1
C15 C 0.2067(3) 0.2993(5) 0.5454(2) 0.0245(8) Uani 1 1 d . . . . .
C11 C 0.5050(3) 0.1222(5) 0.6682(2) 0.0255(8) Uani 1 1 d D . . . .
H11 H 0.530671 0.069109 0.710313 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3760(3) 0.2808(5) 0.6052(2) 0.0249(8) Uani 1 1 d . . . . .
C19 C 0.1250(3) 0.0756(5) 0.4771(2) 0.0236(7) Uani 1 1 d D . . . .
H19 H 0.116188 -0.039465 0.468425 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5179(3) 0.1983(5) 0.5459(2) 0.0266(8) Uani 1 1 d D . . . .
H13 H 0.552330 0.198544 0.504687 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5542(3) 0.1204(5) 0.6071(2) 0.0251(8) Uani 1 1 d D . . . .
C5 C 0.2543(3) 0.4787(5) 0.6547(2) 0.0241(8) Uani 1 1 d . . . . .
C16 C 0.1501(3) 0.4098(5) 0.5032(2) 0.0252(8) Uani 1 1 d . . . . .
C10 C 0.4182(3) 0.2030(5) 0.6661(2) 0.0248(8) Uani 1 1 d . . . . .
C14 C 0.4299(3) 0.2764(5) 0.5461(2) 0.0257(8) Uani 1 1 d . . . . .
C18 C 0.0717(2) 0.1916(5) 0.43719(19) 0.0238(8) Uani 1 1 d D . . . .
C17 C 0.0829(3) 0.3596(5) 0.4497(2) 0.0256(8) Uani 1 1 d D . . . .
H17 H 0.045605 0.438438 0.422427 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2897(3) 0.7346(5) 0.7216(2) 0.0290(8) Uani 1 1 d D . . . .
H7 H 0.331770 0.824714 0.732765 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1914(3) 0.1308(5) 0.5302(2) 0.0236(7) Uani 1 1 d . . . . .
C6 C 0.3126(3) 0.6154(5) 0.6738(2) 0.0249(8) Uani 1 1 d . . . . .
C4 C 0.1697(3) 0.4693(6) 0.6904(2) 0.0309(9) Uani 1 1 d . . . . .
C3 C 0.1443(3) 0.5883(6) 0.7384(2) 0.0352(10) Uani 1 1 d D . . . .
H3 H 0.086349 0.578373 0.760714 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2043(3) 0.7209(6) 0.7532(2) 0.0358(10) Uani 1 1 d D . . . .
C8 C 0.2791(3) 0.3563(7) 0.6018(3) 0.0535(16) Uani 1 1 d . . . . .
Cl9 Cl 0.1749(2) 0.8680(4) 0.81646(16) 0.0747(8) Uani 0.6667 1 d D . P C 2
N1 N 0.1564(12) 0.972(2) 0.8342(8) 0.070(2) Uani 0.3333 1 d D U P C 1
C1 C 0.1733(13) 0.8681(18) 0.8018(6) 0.056(2) Uani 0.3333 1 d D U P C 1
N3 N -0.0453(11) 0.0846(19) 0.3321(8) 0.070(2) Uani 0.3333 1 d D U P B 2
N2 N 0.7114(11) -0.0283(18) 0.6172(8) 0.070(2) Uani 0.3333 1 d D U P A 2
C22 C 0.0011(9) 0.130(2) 0.3732(6) 0.056(2) Uani 0.3333 1 d D U P B 2
C21 C 0.6492(7) 0.0343(13) 0.6085(10) 0.056(2) Uani 0.3333 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.737(4) . ?
Cl4 C20 1.728(4) . ?
Cl6 C14 1.744(4) . ?
Cl3 C16 1.736(4) . ?
Cl7 C10 1.741(4) . ?
Cl2 C4 1.736(5) . ?
Cl8 C12 1.736(4) . ?
Cl5 C18 1.749(4) . ?
C15 C16 1.402(5) . ?
C15 C20 1.404(5) . ?
C15 C8 1.485(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(5) . ?
C11 C10 1.379(5) . ?
C9 C10 1.401(6) . ?
C9 C14 1.399(6) . ?
C9 C8 1.487(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.384(5) . ?
C19 C20 1.387(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.379(5) . ?
C13 C14 1.387(5) . ?
C12 C21 1.502(9) . ?
C5 C6 1.404(5) . ?
C5 C4 1.414(6) . ?
C5 C8 1.469(6) . ?
C16 C17 1.387(5) . ?
C18 C17 1.384(6) . ?
C18 C22 1.583(13) . ?
C17 H17 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.375(5) . ?
C7 C2 1.386(6) . ?
C4 C3 1.388(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.376(7) . ?
C2 Cl9 1.760(5) . ?
C2 C1 1.586(13) . ?
N1 C1 1.075(15) . ?
N3 C22 1.039(15) . ?
N2 C21 1.011(15) . ?

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
C16 C15 C20 115.4(3) . . ?
C16 C15 C8 122.4(4) . . ?
C20 C15 C8 122.2(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.4(4) . . ?
C10 C9 C8 123.0(4) . . ?
C14 C9 C10 115.2(3) . . ?
C14 C9 C8 121.8(4) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(4) . . ?
C20 C19 H19 120.7 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(4) . . ?
C14 C13 H13 120.9 . . ?
C11 C12 Cl8 120.6(3) . . ?
C11 C12 C21 119.3(8) . . ?
C13 C12 Cl8 118.2(3) . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 C21 119.5(8) . . ?
C6 C5 C4 114.4(4) . . ?
C6 C5 C8 122.7(4) . . ?
C4 C5 C8 122.9(4) . . ?
C15 C16 Cl3 119.5(3) . . ?
C17 C16 Cl3 117.0(3) . . ?
C17 C16 C15 123.4(4) . . ?
C11 C10 Cl7 116.5(3) . . ?
C11 C10 C9 123.4(4) . . ?
C9 C10 Cl7 120.0(3) . . ?
C9 C14 Cl6 119.5(3) . . ?
C13 C14 Cl6 116.9(3) . . ?
C13 C14 C9 123.5(4) . . ?
C19 C18 Cl5 119.2(3) . . ?
C19 C18 C22 118.7(8) . . ?
C17 C18 Cl5 119.5(3) . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 C22 119.8(8) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.2(4) . . ?
C18 C17 H17 120.9 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C2 118.9(4) . . ?
C2 C7 H7 120.6 . . ?
C15 C20 Cl4 121.2(3) . . ?
C19 C20 Cl4 115.8(3) . . ?
C19 C20 C15 122.9(4) . . ?
C5 C6 Cl1 120.2(3) . . ?
C7 C6 Cl1 115.9(3) . . ?
C7 C6 C5 123.9(4) . . ?
C5 C4 Cl2 119.9(3) . . ?
C3 C4 Cl2 117.1(3) . . ?
C3 C4 C5 123.0(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C7 C2 Cl9 119.9(4) . . ?
C7 C2 C1 118.5(8) . . ?
C3 C2 C7 120.7(4) . . ?
C3 C2 Cl9 119.4(4) . . ?
C3 C2 C1 120.6(8) . . ?
C15 C8 C9 118.3(4) . . ?
C5 C8 C15 120.9(4) . . ?
C5 C8 C9 120.8(4) . . ?
N1 C1 C2 176.5(19) . . ?
N3 C22 C18 177.9(19) . . ?
N2 C21 C12 171(2) . . ?

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
Cl3 C16 C17 C18 176.8(3) . . . . ?
Cl2 C4 C3 C2 177.3(3) . . . . ?
Cl5 C18 C17 C16 -179.9(3) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C19 C18 C17 C16 0.7(5) . . . . ?
C12 C11 C10 Cl7 178.1(3) . . . . ?
C12 C11 C10 C9 1.3(6) . . . . ?
C12 C13 C14 Cl6 177.2(3) . . . . ?
C12 C13 C14 C9 0.2(6) . . . . ?
C5 C4 C3 C2 -1.0(7) . . . . ?
C16 C15 C20 Cl4 -177.1(3) . . . . ?
C16 C15 C20 C19 0.0(6) . . . . ?
C16 C15 C8 C9 -133.0(5) . . . . ?
C16 C15 C8 C5 49.7(7) . . . . ?
C10 C11 C12 Cl8 -179.7(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C10 C11 C12 C21 179.5(5) . . . . ?
C10 C9 C14 Cl6 -175.5(3) . . . . ?
C10 C9 C14 C13 1.4(6) . . . . ?
C10 C9 C8 C15 -124.0(5) . . . . ?
C10 C9 C8 C5 53.3(7) . . . . ?
C14 C9 C10 Cl7 -178.9(3) . . . . ?
C14 C9 C10 C11 -2.2(6) . . . . ?
C14 C9 C8 C15 53.1(7) . . . . ?
C14 C9 C8 C5 -129.6(5) . . . . ?
C14 C13 C12 Cl8 179.0(3) . . . . ?
C14 C13 C12 C11 -1.2(5) . . . . ?
C14 C13 C12 C21 179.8(5) . . . . ?
C18 C19 C20 Cl4 177.6(3) . . . . ?
C18 C19 C20 C15 0.3(6) . . . . ?
C20 C15 C16 Cl3 -177.1(3) . . . . ?
C20 C15 C16 C17 0.0(6) . . . . ?
C20 C15 C8 C9 46.2(7) . . . . ?
C20 C15 C8 C5 -131.2(5) . . . . ?
C20 C19 C18 Cl5 179.9(3) . . . . ?
C20 C19 C18 C17 -0.7(5) . . . . ?
C20 C19 C18 C22 175.8(5) . . . . ?
C6 C5 C4 Cl2 -176.0(3) . . . . ?
C6 C5 C4 C3 2.3(6) . . . . ?
C6 C5 C8 C15 -134.0(5) . . . . ?
C6 C5 C8 C9 48.7(7) . . . . ?
C6 C7 C2 C3 1.6(6) . . . . ?
C6 C7 C2 Cl9 178.1(3) . . . . ?
C6 C7 C2 C1 -173.6(5) . . . . ?
C4 C5 C6 Cl1 -178.8(3) . . . . ?
C4 C5 C6 C7 -1.8(6) . . . . ?
C4 C5 C8 C15 45.6(8) . . . . ?
C4 C5 C8 C9 -131.6(5) . . . . ?
C4 C3 C2 C7 -1.0(7) . . . . ?
C4 C3 C2 Cl9 -177.6(4) . . . . ?
C4 C3 C2 C1 174.0(5) . . . . ?
C2 C7 C6 Cl1 177.1(3) . . . . ?
C2 C7 C6 C5 -0.1(6) . . . . ?
C8 C15 C16 Cl3 2.1(6) . . . . ?
C8 C15 C16 C17 179.2(4) . . . . ?
C8 C15 C20 Cl4 3.7(6) . . . . ?
C8 C15 C20 C19 -179.2(4) . . . . ?
C8 C9 C10 Cl7 -1.6(5) . . . . ?
C8 C9 C10 C11 175.1(4) . . . . ?
C8 C9 C14 Cl6 7.1(5) . . . . ?
C8 C9 C14 C13 -175.9(4) . . . . ?
C8 C5 C6 Cl1 0.9(6) . . . . ?
C8 C5 C6 C7 177.9(4) . . . . ?
C8 C5 C4 Cl2 4.3(6) . . . . ?
C8 C5 C4 C3 -177.4(4) . . . . ?
C22 C18 C17 C16 -175.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane?methanol'
####################################################################### 
# 
# 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_TTM-2CN
_database_code_depnum_ccdc_archive 'CCDC 2325274'
loop_
_audit_author_name
_audit_author_address
'kuo lv'
;jilin university
China
;
_audit_update_record             
;
2024-01-13 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H6 Cl7 N2'
_chemical_formula_sum            'C21 H6 Cl7 N2'
_chemical_formula_weight         534.43
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2197(11)
_cell_length_b                   11.2036(15)
_cell_length_c                   13.6336(18)
_cell_angle_alpha                67.189(5)
_cell_angle_beta                 84.761(5)
_cell_angle_gamma                73.004(5)
_cell_volume                     1106.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    201.00
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      201.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4448
_reflns_number_total             5069
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.883
_refine_diff_density_min         -1.279
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+2.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C22-C19
 1.53 with sigma of 0.01
 N1-C22
 1.158 with sigma of 0.001
 C19-C22
 1.53 with sigma of 0.0001
 C2-C1
 1.53 with sigma of 0.001
 N3-C1
 1.158 with sigma of 0.01
 C22-C18 \\sim C22-C20
 with sigma of 0.02
 N1-C18 \\sim N1-C20
 with sigma of 0.02
 C1-C3 \\sim C1-C7
 with sigma of 0.02
 N3-C3 \\sim N3-C7
 with sigma of 0.02
3. Restrained planarity
 C20, C19, C18, C22
 with sigma of 0.01
 N1, C22, C18, C20, C19
 with sigma of 0.01
 C2, C1, N3, C3, C7
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Cl8: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
N1 \\sim C22: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C1 \\sim N3: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(C22) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
Uanis(N1) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(Cl8) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
5. Others
 Fixed Sof: Cl1(0.75) C22(0.83) N1(0.83) Cl8(0.25) N3(0.17) C1(0.17)
6.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C7(H7), C3(H3), C13(H13), C20(H20), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl6 Cl 0.44664(8) 0.31369(6) 0.45596(5) 0.02754(14) Uani 1 1 d . . . . .
Cl4 Cl -0.12303(7) 0.28896(7) 0.23053(5) 0.03049(15) Uani 1 1 d . . . . .
Cl3 Cl -0.02712(8) 0.55293(6) 0.30297(5) 0.03037(15) Uani 1 1 d . . . . .
Cl2 Cl 0.28416(8) 0.01111(6) 0.46563(6) 0.03058(15) Uani 1 1 d . . . . .
Cl5 Cl 0.57295(8) 0.13854(8) 0.23484(6) 0.03818(18) Uani 1 1 d . . . . .
Cl7 Cl 0.19080(9) 0.48085(8) 0.05098(5) 0.03599(17) Uani 1 1 d . . . . .
Cl1 Cl -0.22411(15) 0.23236(13) 0.67213(10) 0.0438(3) Uani 0.75 1 d . . P A 2
C10 C 0.0733(3) 0.1989(2) 0.20074(19) 0.0209(5) Uani 1 1 d . . . . .
C16 C 0.3238(3) 0.3956(2) 0.25207(19) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.2255(3) 0.2111(2) 0.23057(19) 0.0212(5) Uani 1 1 d . . . . .
C4 C 0.1322(3) 0.1549(2) 0.4682(2) 0.0227(5) Uani 1 1 d . . . . .
C14 C 0.3766(3) 0.1381(3) 0.1978(2) 0.0242(5) Uani 1 1 d . . . . .
C12 C 0.2230(3) 0.0540(2) 0.11102(19) 0.0221(5) Uani 1 1 d . . . . .
C5 C 0.1238(3) 0.2814(2) 0.38645(19) 0.0203(4) Uani 1 1 d . . . . .
C18 C 0.5200(3) 0.5062(2) 0.2846(2) 0.0239(5) Uani 1 1 d D . . . .
H18 H 0.590662 0.513786 0.332008 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1023(3) 0.3795(3) 0.4867(2) 0.0253(5) Uani 1 1 d D . . . .
H7 H -0.181692 0.456544 0.493670 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0279(3) 0.1379(3) 0.5555(2) 0.0262(5) Uani 1 1 d D . . . .
H3 H 0.036822 0.051051 0.609036 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0039(3) 0.3923(2) 0.40064(19) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.3777(3) 0.0603(3) 0.1397(2) 0.0255(5) Uani 1 1 d . . . . .
H13 H 0.482101 0.012185 0.119651 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3213(3) 0.4816(3) 0.1441(2) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.2231(3) -0.0913(3) 0.0038(2) 0.0414(6) Uani 1 1 d . . . . .
C20 C 0.4128(3) 0.5762(3) 0.1058(2) 0.0269(5) Uani 1 1 d D . . . .
H20 H 0.410128 0.631329 0.032289 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0696(3) 0.1233(3) 0.14127(19) 0.0232(5) Uani 1 1 d . . . . .
H11 H -0.035755 0.118921 0.121507 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2226(3) -0.0294(3) 0.0490(2) 0.0266(5) Uani 1 1 d . . . . .
C17 C 0.4264(3) 0.4130(2) 0.32086(19) 0.0207(4) Uani 1 1 d . . . . .
C2 C -0.0900(3) 0.2517(3) 0.5624(2) 0.0280(5) Uani 1 1 d D . . . .
C8 C 0.2274(3) 0.2957(3) 0.2905(2) 0.0250(5) Uani 1 1 d . . . . .
C19 C 0.5076(2) 0.58693(17) 0.1786(2) 0.0253(5) Uani 1 1 d D . . . .
C22 C 0.6027(3) 0.6949(2) 0.1440(4) 0.0444(10) Uani 0.83 1 d D U P B 1
N1 N 0.6733(4) 0.7770(3) 0.1150(3) 0.0461(7) Uani 0.83 1 d D U P B 1
Cl8 Cl 0.6289(5) 0.7072(4) 0.1223(4) 0.0491(9) Uani 0.25 1 d . U P B 2
N3 N -0.3271(14) 0.2232(12) 0.7059(9) 0.031(3) Uani 0.17 1 d D U P A 1
C1 C -0.2273(10) 0.2340(15) 0.6462(6) 0.029(3) Uani 0.17 1 d D U P A 1


_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
Cl6 C17 1.737(2) . ?
Cl4 C10 1.742(2) . ?
Cl3 C6 1.736(2) . ?
Cl2 C4 1.737(2) . ?
Cl5 C14 1.737(2) . ?
Cl7 C21 1.739(2) . ?
Cl1 C2 1.757(3) . ?
C10 C9 1.409(3) . ?
C10 C11 1.388(3) . ?
C16 C21 1.410(3) . ?
C16 C17 1.418(3) . ?
C16 C8 1.464(3) . ?
C9 C14 1.414(3) . ?
C9 C8 1.476(3) . ?
C4 C5 1.410(3) . ?
C4 C3 1.386(3) . ?
C14 C13 1.385(3) . ?
C12 C13 1.393(3) . ?
C12 C11 1.394(3) . ?
C12 C15 1.484(3) . ?
C5 C6 1.410(3) . ?
C5 C8 1.475(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.388(3) . ?
C18 C19 1.370(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(3) . ?
C7 C2 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.388(4) . ?
C13 H13 0.9500 . ?
C21 C20 1.388(3) . ?
N2 C15 1.091(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.377(4) . ?
C11 H11 0.9500 . ?
C2 C1 1.5293(10) . ?
C19 C22 1.52994(19) . ?
C19 Cl8 1.800(5) . ?
C22 N1 1.1524(10) . ?
N3 C1 1.100(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C10 Cl4 120.46(18) . . ?
C11 C10 Cl4 116.42(18) . . ?
C11 C10 C9 123.0(2) . . ?
C21 C16 C17 115.2(2) . . ?
C21 C16 C8 122.5(2) . . ?
C17 C16 C8 122.4(2) . . ?
C10 C9 C14 115.3(2) . . ?
C10 C9 C8 122.4(2) . . ?
C14 C9 C8 122.2(2) . . ?
C5 C4 Cl2 120.13(18) . . ?
C3 C4 Cl2 116.5(2) . . ?
C3 C4 C5 123.3(2) . . ?
C9 C14 Cl5 119.82(18) . . ?
C13 C14 Cl5 116.94(19) . . ?
C13 C14 C9 123.2(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 C15 119.3(2) . . ?
C11 C12 C15 120.0(2) . . ?
C4 C5 C8 122.3(2) . . ?
C6 C5 C4 115.2(2) . . ?
C6 C5 C8 122.4(2) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C19 C18 C17 118.2(2) . . ?
C6 C7 H7 120.8 . . ?
C2 C7 H7 120.8 . . ?
C2 C7 C6 118.3(2) . . ?
C4 C3 H3 121.0 . . ?
C4 C3 C2 118.0(2) . . ?
C2 C3 H3 121.0 . . ?
C5 C6 Cl3 120.11(18) . . ?
C7 C6 Cl3 116.56(18) . . ?
C7 C6 C5 123.2(2) . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C16 C21 Cl7 120.86(18) . . ?
C20 C21 Cl7 115.6(2) . . ?
C20 C21 C16 123.5(2) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 C21 117.3(2) . . ?
C19 C20 H20 121.3 . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N2 C15 C12 179.5(3) . . ?
C16 C17 Cl6 121.25(18) . . ?
C18 C17 Cl6 116.14(18) . . ?
C18 C17 C16 122.6(2) . . ?
C7 C2 Cl1 119.3(2) . . ?
C7 C2 C3 122.0(2) . . ?
C7 C2 C1 118.4(6) . . ?
C3 C2 Cl1 118.7(2) . . ?
C3 C2 C1 119.0(6) . . ?
C16 C8 C9 120.3(2) . . ?
C16 C8 C5 121.3(2) . . ?
C5 C8 C9 118.4(2) . . ?
C18 C19 C20 123.3(2) . . ?
C18 C19 C22 116.2(3) . . ?
C18 C19 Cl8 121.9(2) . . ?
C20 C19 C22 120.5(3) . . ?
C20 C19 Cl8 114.7(2) . . ?
N1 C22 C19 178.1(5) . . ?
N3 C1 C2 179.0(16) . . ?

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
Cl4 C10 C9 C14 -177.20(19) . . . . ?
Cl4 C10 C9 C8 2.0(3) . . . . ?
Cl4 C10 C11 C12 177.17(19) . . . . ?
Cl2 C4 C5 C6 -175.60(17) . . . . ?
Cl2 C4 C5 C8 7.2(3) . . . . ?
Cl2 C4 C3 C2 177.26(19) . . . . ?
Cl5 C14 C13 C12 178.2(2) . . . . ?
Cl7 C21 C20 C19 175.17(15) . . . . ?
C10 C9 C14 Cl5 -177.06(19) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C10 C9 C8 C16 -128.4(3) . . . . ?
C10 C9 C8 C5 48.8(3) . . . . ?
C16 C21 C20 C19 -1.3(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C9 C14 C13 C12 0.5(4) . . . . ?
C4 C5 C6 Cl3 -176.86(17) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C4 C5 C8 C16 -132.1(3) . . . . ?
C4 C5 C8 C9 50.7(3) . . . . ?
C4 C3 C2 Cl1 179.7(2) . . . . ?
C4 C3 C2 C7 -1.6(4) . . . . ?
C4 C3 C2 C1 169.2(4) . . . . ?
C14 C9 C8 C16 50.7(4) . . . . ?
C14 C9 C8 C5 -132.1(3) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C3 C4 C5 C8 -175.4(2) . . . . ?
C6 C5 C8 C16 50.9(3) . . . . ?
C6 C5 C8 C9 -126.3(3) . . . . ?
C6 C7 C2 Cl1 -179.66(19) . . . . ?
C6 C7 C2 C3 1.7(4) . . . . ?
C6 C7 C2 C1 -169.1(4) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
C21 C16 C17 Cl6 -178.98(17) . . . . ?
C21 C16 C17 C18 -1.0(3) . . . . ?
C21 C16 C8 C9 43.8(4) . . . . ?
C21 C16 C8 C5 -133.3(3) . . . . ?
C21 C20 C19 C18 2.4(3) . . . . ?
C21 C20 C19 C22 -176.0(2) . . . . ?
C21 C20 C19 Cl8 177.8(2) . . . . ?
C11 C10 C9 C14 -1.4(4) . . . . ?
C11 C10 C9 C8 177.7(2) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C15 C12 C13 C14 -179.8(2) . . . . ?
C15 C12 C11 C10 179.0(2) . . . . ?
C17 C16 C21 Cl7 -175.67(17) . . . . ?
C17 C16 C21 C20 0.6(3) . . . . ?
C17 C16 C8 C9 -136.4(2) . . . . ?
C17 C16 C8 C5 46.5(3) . . . . ?
C17 C18 C19 C20 -2.9(3) . . . . ?
C17 C18 C19 C22 175.68(19) . . . . ?
C17 C18 C19 Cl8 -177.8(2) . . . . ?
C2 C7 C6 Cl3 175.4(2) . . . . ?
C2 C7 C6 C5 0.0(4) . . . . ?
C8 C16 C21 Cl7 4.2(3) . . . . ?
C8 C16 C21 C20 -179.5(2) . . . . ?
C8 C16 C17 Cl6 1.1(3) . . . . ?
C8 C16 C17 C18 179.1(2) . . . . ?
C8 C9 C14 Cl5 3.8(3) . . . . ?
C8 C9 C14 C13 -178.6(2) . . . . ?
C8 C5 C6 Cl3 0.3(3) . . . . ?
C8 C5 C6 C7 175.5(2) . . . . ?
C19 C18 C17 Cl6 -179.84(14) . . . . ?
C19 C18 C17 C16 2.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
