# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2160757'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_chemical_name_systematic        
'8-tert-butyl-1,2-diphenyltribenzo[b,g,ij]imidazo[2,1,5-de]quinolizin-1-ium chloride'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H29 Cl N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         537.07

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   30.678(3)
_cell_length_b                   6.7193(5)
_cell_length_c                   13.7302(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.728(4)
_cell_angle_gamma                90
_cell_volume                     2760.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3117
_cell_measurement_theta_min      2.7227
_cell_measurement_theta_max      26.5447
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128

_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Sevvana, M., Ruf, M., Usón, I., Sheldrick, G. M., and Herbst-Irmer, R. (2019)
"Non-merohedral twinning: from minerals to proteins"
Acta. Cryst. D75, 1040-1050.
doi:10.1107/S2059798319010179
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             ?
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            3825
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             3825
_reflns_number_gt                2177
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1965
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.033
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     298
_refine_ls_number_restraints     274
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0821P)²+1.8890P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.31769(15) 0.500000 0.3645(4) 0.0256(11) Uani d TU P DS 1.000000 . .
C C2 0.3612(7) 0.500000 0.2607(18) 0.027(2) Uani d TU P DS 0.60(4) A 1
N N2 0.3609(5) 0.500000 0.3587(13) 0.024(2) Uani d TU P DS 0.60(4) A 1
C C2A 0.3603(9) 0.500000 0.346(3) 0.026(3) Uani d TU P DS 0.40(4) A 2
N N2A 0.3618(8) 0.500000 0.249(2) 0.024(2) Uani d TU P DS 0.40(4) A 2
C C3 0.31863(14) 0.500000 0.2005(4) 0.0247(11) Uani d TU P DS 1.000000 . .
C C4 0.24572(12) 0.500000 0.2442(4) 0.0208(8) Uani d T P S 1.000000 . .
C C5 0.22451(16) 0.500000 0.1425(4) 0.0235(11) Uani d T P S 1.000000 A .
C C6 0.17786(16) 0.500000 0.1219(4) 0.0259(11) Uani d T P S 1.000000 . .
H H6 0.161997 0.500000 0.054157 0.031000 Uiso calc U P R 1.000000 A .
C C7 0.15360(13) 0.500000 0.1967(5) 0.0253(10) Uani d T P DS 1.000000 A .
C C8 0.17661(16) 0.500000 0.2960(4) 0.0251(11) Uani d T P S 1.000000 . .
H H8 0.160223 0.500000 0.347238 0.030000 Uiso calc U P R 1.000000 A .
C C9 0.22348(15) 0.500000 0.3223(4) 0.0219(11) Uani d T P S 1.000000 A .
C C10 0.29652(17) 0.500000 0.4480(4) 0.0212(11) Uani d T P S 1.000000 A .
C C11 0.24881(18) 0.500000 0.4264(4) 0.0240(12) Uani d T P S 1.000000 . .
C C12 0.22784(16) 0.500000 0.5069(4) 0.0278(12) Uani d T P S 1.000000 A .
H H12 0.196119 0.500000 0.494262 0.033000 Uiso calc U P R 1.000000 . .
C C13 0.2522(2) 0.500000 0.6048(4) 0.0302(13) Uani d T P S 1.000000 . .
H H13 0.237253 0.500000 0.658445 0.036000 Uiso calc U P R 1.000000 A .
C C14 0.2987(2) 0.500000 0.6242(4) 0.0335(14) Uani d T P S 1.000000 A .
H H14 0.315361 0.500000 0.691331 0.040000 Uiso calc U P R 1.000000 . .
C C15 0.32056(15) 0.500000 0.5477(5) 0.0291(11) Uani d T P S 1.000000 . .
H H15 0.352304 0.500000 0.562043 0.035000 Uiso calc U P R 1.000000 A .
C C16 0.40130(16) 0.500000 0.4351(4) 0.0306(12) Uani d T P S 1.000000 . .
C C17 0.41850(12) 0.6797(6) 0.4740(3) 0.0392(10) Uani d . . . 1.000000 . .
H H17 0.405711 0.801584 0.446426 0.047000 Uiso calc U . R 1.000000 . .
C C18 0.45484(13) 0.6785(7) 0.5542(3) 0.0508(12) Uani d . . . 1.000000 . .
H H18 0.467298 0.800514 0.582331 0.061000 Uiso calc U . R 1.000000 . .
C C19 0.47298(18) 0.500000 0.5933(5) 0.0531(17) Uani d T P S 1.000000 . .
H H19 0.498227 0.500002 0.647627 0.064000 Uiso calc U P R 1.000000 . .
C C22 0.40284(16) 0.500000 0.2170(4) 0.0291(12) Uani d T P S 1.000000 . .
C C23 0.42140(13) 0.6787(6) 0.1990(3) 0.0405(10) Uani d . . . 1.000000 . .
H H23 0.408809 0.801012 0.214040 0.049000 Uiso calc U . R 1.000000 . .
C C24 0.45929(13) 0.6764(7) 0.1578(3) 0.0462(11) Uani d . . . 1.000000 . .
H H24 0.472552 0.798233 0.144401 0.055000 Uiso calc U . R 1.000000 . .
C C25 0.47727(18) 0.500000 0.1368(4) 0.0438(16) Uani d T P S 1.000000 . .
H H25 0.502516 0.499998 0.107241 0.053000 Uiso calc U P R 1.000000 . .
C C28 0.29806(18) 0.500000 0.0956(4) 0.0262(12) Uani d T P S 1.000000 A .
C C29 0.32311(14) 0.500000 0.0214(4) 0.0258(11) Uani d T P S 1.000000 . .
H H29 0.354819 0.500000 0.040281 0.031000 Uiso calc U P R 1.000000 A .
C C30 0.30239(19) 0.500000 -0.0780(4) 0.0281(13) Uani d T P S 1.000000 A .
H H30 0.319829 0.500000 -0.127277 0.034000 Uiso calc U P R 1.000000 . .
C C31 0.25624(19) 0.500000 -0.1069(4) 0.0302(13) Uani d T P S 1.000000 . .
H H31 0.242030 0.500000 -0.175724 0.036000 Uiso calc U P R 1.000000 A .
C C32 0.23073(16) 0.500000 -0.0350(4) 0.0253(12) Uani d T P S 1.000000 A .
H H32 0.199052 0.500000 -0.055031 0.030000 Uiso calc U P R 1.000000 . .
C C33 0.25124(17) 0.500000 0.0669(4) 0.0221(11) Uani d T P S 1.000000 . .
C C34 0.10205(17) 0.493(11) 0.1658(11) 0.032(3) Uani d U P D 0.375(8) A -1
C C35 0.0881(5) 0.284(2) 0.1267(13) 0.043(3) Uani d U P D 0.375(8) A -1
H H35A 0.101286 0.254726 0.069378 0.064000 Uiso calc U P R 0.375(8) A -1
H H35B 0.055495 0.276989 0.106057 0.064000 Uiso calc U P R 0.375(8) A -1
H H35C 0.098736 0.186268 0.179622 0.064000 Uiso calc U P R 0.375(8) A -1
C C36 0.0810(3) 0.541(2) 0.2572(8) 0.036(3) Uani d U P D 0.375(8) A -1
H H36A 0.088835 0.435968 0.307396 0.054000 Uiso calc U P R 0.375(8) A -1
H H36B 0.048422 0.549116 0.234949 0.054000 Uiso calc U P R 0.375(8) A -1
H H36C 0.092579 0.668941 0.286439 0.054000 Uiso calc U P R 0.375(8) A -1
C C37 0.0845(5) 0.652(2) 0.0877(10) 0.041(3) Uani d U P D 0.375(8) A -1
H H37A 0.095378 0.783305 0.113835 0.062000 Uiso calc U P R 0.375(8) A -1
H H37B 0.051767 0.651693 0.072282 0.062000 Uiso calc U P R 0.375(8) A -1
H H37C 0.095155 0.624661 0.026791 0.062000 Uiso calc U P R 0.375(8) A -1
C C34A 0.1023(3) 0.498(10) 0.182(3) 0.038(4) Uani d U P D 0.125(8) A -2
C C35A 0.0847(12) 0.648(5) 0.248(2) 0.044(6) Uani d U P D 0.125(8) A -2
H H35D 0.097211 0.617726 0.318262 0.066000 Uiso calc U P R 0.125(8) A -2
H H35E 0.052024 0.639792 0.234617 0.066000 Uiso calc U P R 0.125(8) A -2
H H35F 0.093571 0.782663 0.232762 0.066000 Uiso calc U P R 0.125(8) A -2
C C36A 0.0835(10) 0.543(6) 0.0690(19) 0.041(5) Uani d U P D 0.125(8) A -2
H H36D 0.092627 0.677312 0.053540 0.061000 Uiso calc U P R 0.125(8) A -2
H H36E 0.050830 0.535081 0.054000 0.061000 Uiso calc U P R 0.125(8) A -2
H H36F 0.095365 0.445647 0.028500 0.061000 Uiso calc U P R 0.125(8) A -2
C C37A 0.0901(11) 0.284(4) 0.201(3) 0.041(5) Uani d U P D 0.125(8) A -2
H H37D 0.102283 0.194618 0.157239 0.061000 Uiso calc U P R 0.125(8) A -2
H H37E 0.057518 0.270165 0.187162 0.061000 Uiso calc U P R 0.125(8) A -2
H H37F 0.102702 0.249126 0.270903 0.061000 Uiso calc U P R 0.125(8) A -2
Cl Cl1 0.34538(4) 0.000000 0.29197(15) 0.0392(3) Uani d T P S 1.000000 . .
N N1 0.29210(10) 0.500000 0.2690(4) 0.0231(7) Uani d T P S 1.000000 A .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.345(18) ?
C1 N1 . 1.372(6) ?
C1 C2A . 1.38(2) ?
C1 C10 . 1.436(7) ?
C2 N2 . 1.347(9) ?
C2 C3 . 1.38(2) ?
C2 C22 . 1.53(2) ?
N2 C16 . 1.437(17) ?
C2A N2A . 1.347(10) ?
C2A C16 . 1.55(3) ?
N2A C3 . 1.35(2) ?
N2A C22 . 1.42(3) ?
C3 N1 . 1.373(6) ?
C3 C28 . 1.439(7) ?
C4 N1 . 1.388(5) ?
C4 C9 . 1.392(7) ?
C4 C5 . 1.405(7) ?
C5 C6 . 1.396(7) ?
C5 C33 . 1.457(7) ?
C6 C7 . 1.395(7) ?
C6 H6 . 0.950000 ?
C7 C8 . 1.391(7) ?
C7 C34A . 1.543(10) ?
C7 C34 . 1.545(7) ?
C8 C9 . 1.403(6) ?
C8 H8 . 0.950000 ?
C9 C11 . 1.468(7) ?
C10 C15 . 1.405(7) ?
C10 C11 . 1.428(7) ?
C11 C12 . 1.395(8) ?
C12 C13 . 1.388(8) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.391(9) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.365(8) ?
C14 H14 . 0.950000 ?
C15 H15 . 0.950000 ?
C16 C17 . 1.377(5) ?
C16 C17 6_565 1.377(5) ?
C17 C18 . 1.383(5) ?
C17 H17 . 0.950000 ?
C18 C19 . 1.380(5) ?
C18 H18 . 0.950000 ?
C19 H19 . 0.950000 ?
C22 C23 . 1.375(5) ?
C22 C23 6_565 1.375(5) ?
C23 C24 . 1.400(6) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.365(5) ?
C24 H24 . 0.950000 ?
C25 H25 . 0.950000 ?
C28 C33 . 1.403(7) ?
C28 C29 . 1.405(7) ?
C29 C30 . 1.373(7) ?
C29 H29 . 0.950000 ?
C30 C31 . 1.384(8) ?
C30 H30 . 0.950000 ?
C31 C32 . 1.388(7) ?
C31 H31 . 0.950000 ?
C32 C33 . 1.402(7) ?
C32 H32 . 0.950000 ?
C34 C35 . 1.53(7) ?
C34 C37 . 1.53(5) ?
C34 C36 . 1.57(3) ?
C35 H35A . 0.980000 ?
C35 H35B . 0.980000 ?
C35 H35C . 0.980000 ?
C36 H36A . 0.980000 ?
C36 H36B . 0.980000 ?
C36 H36C . 0.980000 ?
C37 H37A . 0.980000 ?
C37 H37B . 0.980000 ?
C37 H37C . 0.980000 ?
C34A C35A . 1.53(7) ?
C34A C37A . 1.52(5) ?
C34A C36A . 1.56(3) ?
C35A H35D . 0.980000 ?
C35A H35E . 0.980000 ?
C35A H35F . 0.980000 ?
C36A H36D . 0.980000 ?
C36A H36E . 0.980000 ?
C36A H36F . 0.980000 ?
C37A H37D . 0.980000 ?
C37A H37E . 0.980000 ?
C37A H37F . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 107.9(8) ?
N1 C1 C2A . . 101.1(14) ?
N2 C1 C10 . . 132.2(9) ?
N1 C1 C10 . . 119.9(4) ?
C2A C1 C10 . . 139.0(15) ?
N2 C2 C3 . . 113.(2) ?
N2 C2 C22 . . 126.(2) ?
C3 C2 C22 . . 121.8(17) ?
C1 N2 C2 . . 106.5(18) ?
C1 N2 C16 . . 131.2(14) ?
C2 N2 C16 . . 122.(2) ?
N2A C2A C1 . . 115.(3) ?
N2A C2A C16 . . 126.(3) ?
C1 C2A C16 . . 120.(2) ?
C3 N2A C2A . . 104.(3) ?
C3 N2A C22 . . 134.(2) ?
C2A N2A C22 . . 122.(3) ?
N2A C3 N1 . . 109.1(12) ?
N1 C3 C2 . . 102.4(10) ?
N2A C3 C28 . . 131.5(13) ?
N1 C3 C28 . . 119.3(4) ?
C2 C3 C28 . . 138.3(11) ?
N1 C4 C9 . . 117.4(5) ?
N1 C4 C5 . . 118.0(5) ?
C9 C4 C5 . . 124.6(3) ?
C6 C5 C4 . . 115.5(5) ?
C6 C5 C33 . . 124.6(5) ?
C4 C5 C33 . . 119.9(4) ?
C5 C6 C7 . . 122.7(5) ?
C5 C6 H6 . . 118.600000 ?
C7 C6 H6 . . 118.600000 ?
C8 C7 C6 . . 119.0(4) ?
C8 C7 C34A . . 114.2(17) ?
C6 C7 C34A . . 126.9(17) ?
C8 C7 C34 . . 122.5(7) ?
C6 C7 C34 . . 118.6(8) ?
C7 C8 C9 . . 121.5(5) ?
C7 C8 H8 . . 119.300000 ?
C9 C8 H8 . . 119.300000 ?
C4 C9 C8 . . 116.7(5) ?
C4 C9 C11 . . 120.4(4) ?
C8 C9 C11 . . 122.9(5) ?
C15 C10 C11 . . 119.7(5) ?
C15 C10 C1 . . 123.0(4) ?
C11 C10 C1 . . 117.2(5) ?
C12 C11 C10 . . 117.8(5) ?
C12 C11 C9 . . 122.2(4) ?
C10 C11 C9 . . 120.0(5) ?
C13 C12 C11 . . 121.5(4) ?
C13 C12 H12 . . 119.200000 ?
C11 C12 H12 . . 119.200000 ?
C12 C13 C14 . . 119.8(5) ?
C12 C13 H13 . . 120.100000 ?
C14 C13 H13 . . 120.100000 ?
C15 C14 C13 . . 120.6(5) ?
C15 C14 H14 . . 119.700000 ?
C13 C14 H14 . . 119.700000 ?
C14 C15 C10 . . 120.6(4) ?
C14 C15 H15 . . 119.700000 ?
C10 C15 H15 . . 119.700000 ?
C17 C16 C17 . 6_565 122.5(5) ?
C17 C16 N2 . . 118.6(2) ?
C17 C16 N2 6_565 . 118.6(2) ?
C17 C16 C2A . . 118.8(3) ?
C17 C16 C2A 6_565 . 118.8(3) ?
C16 C17 C18 . . 118.4(4) ?
C16 C17 H17 . . 120.800000 ?
C18 C17 H17 . . 120.800000 ?
C19 C18 C17 . . 120.0(5) ?
C19 C18 H18 . . 120.000000 ?
C17 C18 H18 . . 120.000000 ?
C18 C19 C18 . 6_565 120.7(6) ?
C18 C19 H19 . . 119.600000 ?
C18 C19 H19 6_565 . 119.600000 ?
C23 C22 C23 . 6_565 121.7(5) ?
C23 C22 N2A . . 119.1(3) ?
C23 C22 N2A 6_565 . 119.1(3) ?
C23 C22 C2 . . 119.1(3) ?
C23 C22 C2 6_565 . 119.1(3) ?
C22 C23 C24 . . 118.5(4) ?
C22 C23 H23 . . 120.800000 ?
C24 C23 H23 . . 120.800000 ?
C25 C24 C23 . . 120.4(4) ?
C25 C24 H24 . . 119.800000 ?
C23 C24 H24 . . 119.800000 ?
C24 C25 C24 . 6_565 120.6(6) ?
C24 C25 H25 . . 119.700000 ?
C24 C25 H25 6_565 . 119.700000 ?
C33 C28 C29 . . 119.1(5) ?
C33 C28 C3 . . 118.5(5) ?
C29 C28 C3 . . 122.4(5) ?
C30 C29 C28 . . 120.9(4) ?
C30 C29 H29 . . 119.500000 ?
C28 C29 H29 . . 119.500000 ?
C29 C30 C31 . . 120.3(5) ?
C29 C30 H30 . . 119.800000 ?
C31 C30 H30 . . 119.800000 ?
C30 C31 C32 . . 119.9(5) ?
C30 C31 H31 . . 120.100000 ?
C32 C31 H31 . . 120.100000 ?
C31 C32 C33 . . 120.7(4) ?
C31 C32 H32 . . 119.700000 ?
C33 C32 H32 . . 119.700000 ?
C32 C33 C28 . . 119.1(5) ?
C32 C33 C5 . . 120.8(4) ?
C28 C33 C5 . . 120.1(5) ?
C35 C34 C37 . . 111.7(17) ?
C35 C34 C7 . . 108.(4) ?
C37 C34 C7 . . 111.(3) ?
C35 C34 C36 . . 110.(3) ?
C37 C34 C36 . . 106.(4) ?
C7 C34 C36 . . 110.6(16) ?
C34 C35 H35A . . 109.500000 ?
C34 C35 H35B . . 109.500000 ?
H35A C35 H35B . . 109.500000 ?
C34 C35 H35C . . 109.500000 ?
H35A C35 H35C . . 109.500000 ?
H35B C35 H35C . . 109.500000 ?
C34 C36 H36A . . 109.500000 ?
C34 C36 H36B . . 109.500000 ?
H36A C36 H36B . . 109.500000 ?
C34 C36 H36C . . 109.500000 ?
H36A C36 H36C . . 109.500000 ?
H36B C36 H36C . . 109.500000 ?
C34 C37 H37A . . 109.500000 ?
C34 C37 H37B . . 109.500000 ?
H37A C37 H37B . . 109.500000 ?
C34 C37 H37C . . 109.500000 ?
H37A C37 H37C . . 109.500000 ?
H37B C37 H37C . . 109.500000 ?
C35A C34A C37A . . 113.(2) ?
C35A C34A C7 . . 114.(4) ?
C37A C34A C7 . . 105.(3) ?
C35A C34A C36A . . 111.(3) ?
C37A C34A C36A . . 108.(4) ?
C7 C34A C36A . . 106.(2) ?
C34A C35A H35D . . 109.500000 ?
C34A C35A H35E . . 109.500000 ?
H35D C35A H35E . . 109.500000 ?
C34A C35A H35F . . 109.500000 ?
H35D C35A H35F . . 109.500000 ?
H35E C35A H35F . . 109.500000 ?
C34A C36A H36D . . 109.500000 ?
C34A C36A H36E . . 109.500000 ?
H36D C36A H36E . . 109.500000 ?
C34A C36A H36F . . 109.500000 ?
H36D C36A H36F . . 109.500000 ?
H36E C36A H36F . . 109.500000 ?
C34A C37A H37D . . 109.500000 ?
C34A C37A H37E . . 109.500000 ?
H37D C37A H37E . . 109.500000 ?
C34A C37A H37F . . 109.500000 ?
H37D C37A H37F . . 109.500000 ?
H37E C37A H37F . . 109.500000 ?
C3 N1 C1 . . 110.7(3) ?
C3 N1 C4 . . 124.2(5) ?
C1 N1 C4 . . 125.0(5) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_3m
_database_code_depnum_ccdc_archive 'CCDC 2160758'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H32 Cl2 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         623.54

_chemical_melting_point          ?

_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                   11.6921(13)
_cell_length_b                   11.7421(12)
_cell_length_c                   12.1976(12)
_cell_angle_alpha                85.354(3)
_cell_angle_beta                 62.684(3)
_cell_angle_gamma                88.515(3)
_cell_volume                     1482.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.5719
_cell_measurement_theta_max      26.4032
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652

_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            34882
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             6096
_reflns_number_gt                4010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2155
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         6096
_refine_ls_number_parameters     440
_refine_ls_number_restraints     163
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²+3.9989P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.932
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5937(4) 0.6493(3) 0.3771(4) 0.0251(8) Uani d . . . 1.000000 . .
C C2 0.5949(4) 0.6843(3) 0.1950(4) 0.0311(9) Uani d . . . 1.000000 . .
C C3 0.6737(4) 0.5916(3) 0.1865(4) 0.0286(9) Uani d . . . 1.000000 . .
C C4 0.7399(4) 0.4957(3) 0.3395(4) 0.0271(9) Uani d . . . 1.000000 . .
C C5 0.8278(4) 0.4276(3) 0.2505(4) 0.0296(9) Uani d . . . 1.000000 . .
C C6 0.8989(4) 0.3523(3) 0.2884(4) 0.0337(10) Uani d . . . 1.000000 . .
H H6 0.958903 0.304177 0.230281 0.040000 Uiso calc U . R 1.000000 . .
C C7 0.8858(4) 0.3448(3) 0.4087(4) 0.0347(10) Uani d . . D 1.000000 . .
C C8 0.7960(4) 0.4143(3) 0.4933(4) 0.0313(9) Uani d . . . 1.000000 . .
H H8 0.785282 0.409113 0.575579 0.038000 Uiso calc U . R 1.000000 . .
C C9 0.7208(4) 0.4918(3) 0.4617(4) 0.0266(8) Uani d . . . 1.000000 . .
C C10 0.5676(4) 0.6503(3) 0.5010(4) 0.0261(8) Uani d . . . 1.000000 . .
C C11 0.6283(4) 0.5690(3) 0.5485(4) 0.0260(8) Uani d . . . 1.000000 . .
C C12 0.5952(4) 0.5696(3) 0.6737(4) 0.0296(9) Uani d . . . 1.000000 . .
H H12 0.632493 0.516212 0.710428 0.035000 Uiso calc U . R 1.000000 . .
C C13 0.5076(4) 0.6485(3) 0.7445(4) 0.0309(9) Uani d . . . 1.000000 . .
H H13 0.485258 0.647184 0.829951 0.037000 Uiso calc U . R 1.000000 . .
C C14 0.4515(4) 0.7291(3) 0.6960(4) 0.0297(9) Uani d . . . 1.000000 . .
H H14 0.392292 0.781929 0.747673 0.036000 Uiso calc U . R 1.000000 . .
C C15 0.4817(4) 0.7327(3) 0.5713(4) 0.0273(9) Uani d . . . 1.000000 . .
C C16 0.4723(4) 0.8147(3) 0.3778(4) 0.0288(9) Uani d . . . 1.000000 . .
C C17 0.4355(4) 0.8167(3) 0.5060(4) 0.0290(9) Uani d . . . 1.000000 . .
C C18 0.3608(4) 0.9092(4) 0.5660(4) 0.0323(9) Uani d . . . 1.000000 . .
H H18 0.332292 0.911928 0.652274 0.039000 Uiso calc U . R 1.000000 . .
C C19 0.3279(4) 0.9959(4) 0.5038(4) 0.0333(10) Uani d . . . 1.000000 . .
H H19 0.276597 1.057116 0.546980 0.040000 Uiso calc U . R 1.000000 . .
C C20 0.3695(4) 0.9938(4) 0.3781(4) 0.0361(10) Uani d . . . 1.000000 . .
H H20 0.348736 1.055044 0.334743 0.043000 Uiso calc U . R 1.000000 . .
C C21 0.4407(4) 0.9041(4) 0.3151(4) 0.0348(10) Uani d . . . 1.000000 . .
H H21 0.468234 0.903287 0.228789 0.042000 Uiso calc U . R 1.000000 . .
C C22 0.5594(4) 0.7472(3) 0.1051(4) 0.0298(9) Uani d . . . 1.000000 . .
C C23 0.6476(4) 0.8190(4) 0.0099(4) 0.0368(10) Uani d . . . 1.000000 . .
H H23 0.732104 0.827575 0.001010 0.044000 Uiso calc U . R 1.000000 . .
C C24 0.6124(5) 0.8784(4) -0.0722(4) 0.0395(11) Uani d . . . 1.000000 . .
H H24 0.673048 0.927743 -0.137637 0.047000 Uiso calc U . R 1.000000 . .
C C25 0.4906(5) 0.8667(4) -0.0600(4) 0.0388(11) Uani d . . . 1.000000 . .
H H25 0.466866 0.908119 -0.116487 0.047000 Uiso calc U . R 1.000000 . .
C C26 0.4021(4) 0.7942(4) 0.0354(4) 0.0369(10) Uani d . . . 1.000000 . .
H H26 0.317924 0.785394 0.043532 0.044000 Uiso calc U . R 1.000000 . .
C C27 0.4357(4) 0.7354(3) 0.1174(4) 0.0320(9) Uani d . . . 1.000000 . .
H H27 0.374568 0.686400 0.182948 0.038000 Uiso calc U . R 1.000000 . .
C C28 0.7556(4) 0.5126(3) 0.0944(4) 0.0315(9) Uani d . . . 1.000000 . .
C C29 0.7615(5) 0.5020(4) -0.0222(4) 0.0403(11) Uani d . . . 1.000000 . .
C C30 0.8503(5) 0.4348(4) -0.1083(4) 0.0407(11) Uani d . . . 1.000000 . .
H H30 0.853541 0.433245 -0.187369 0.049000 Uiso calc U . R 1.000000 . .
C C31 0.9333(5) 0.3709(4) -0.0806(4) 0.0416(12) Uani d . . . 1.000000 . .
H H31 0.996387 0.326429 -0.140903 0.050000 Uiso calc U . R 1.000000 . .
C C32 0.9252(4) 0.3708(4) 0.0363(4) 0.0378(11) Uani d . . . 1.000000 . .
H H32 0.981315 0.323729 0.056376 0.045000 Uiso calc U . R 1.000000 . .
C C33 0.8364(4) 0.4385(3) 0.1252(4) 0.0327(10) Uani d . . . 1.000000 . .
C C34 0.9686(7) 0.2613(7) 0.4445(7) 0.037(2) Uani d U P D 0.579(13) A 1
C C35 0.8972(10) 0.2137(10) 0.5801(7) 0.056(3) Uani d U P D 0.579(13) A 1
H H35A 0.953697 0.162001 0.599526 0.083000 Uiso calc U P R 0.579(13) A 1
H H35B 0.819921 0.171708 0.593433 0.083000 Uiso calc U P R 0.579(13) A 1
H H35C 0.872245 0.276874 0.634049 0.083000 Uiso calc U P R 0.579(13) A 1
C C36 1.0849(12) 0.3309(9) 0.4281(14) 0.059(3) Uani d U P D 0.579(13) A 1
H H36A 1.140104 0.282295 0.452403 0.089000 Uiso calc U P R 0.579(13) A 1
H H36B 1.055280 0.395483 0.480143 0.089000 Uiso calc U P R 0.579(13) A 1
H H36C 1.133742 0.359634 0.341155 0.089000 Uiso calc U P R 0.579(13) A 1
C C37 1.0147(13) 0.1598(9) 0.3644(11) 0.051(3) Uani d U P D 0.579(13) A 1
H H37A 1.058492 0.105473 0.397261 0.077000 Uiso calc U P R 0.579(13) A 1
H H37B 1.074467 0.186895 0.279233 0.077000 Uiso calc U P R 0.579(13) A 1
H H37C 0.940506 0.121864 0.365246 0.077000 Uiso calc U P R 0.579(13) A 1
C C34A 0.9794(10) 0.2741(10) 0.4429(10) 0.038(3) Uani d U P D 0.421(13) A 2
C C35A 0.9531(16) 0.2784(15) 0.5779(10) 0.064(4) Uani d U P D 0.421(13) A 2
H H35D 1.002066 0.218571 0.597890 0.096000 Uiso calc U P R 0.421(13) A 2
H H35E 0.860945 0.266111 0.632838 0.096000 Uiso calc U P R 0.421(13) A 2
H H35F 0.979485 0.353316 0.589224 0.096000 Uiso calc U P R 0.421(13) A 2
C C36A 1.1183(12) 0.3173(12) 0.3620(15) 0.048(3) Uani d U P D 0.421(13) A 2
H H36D 1.177044 0.269769 0.382433 0.072000 Uiso calc U P R 0.421(13) A 2
H H36E 1.125624 0.396757 0.377424 0.072000 Uiso calc U P R 0.421(13) A 2
H H36F 1.140828 0.312963 0.274530 0.072000 Uiso calc U P R 0.421(13) A 2
C C37A 0.9707(17) 0.1489(11) 0.4202(18) 0.058(4) Uani d U P D 0.421(13) A 2
H H37D 1.035113 0.104438 0.434943 0.087000 Uiso calc U P R 0.421(13) A 2
H H37E 0.986930 0.143838 0.334487 0.087000 Uiso calc U P R 0.421(13) A 2
H H37F 0.884535 0.118328 0.476722 0.087000 Uiso calc U P R 0.421(13) A 2
Cl Cl1 0.64812(17) 0.56130(13) -0.06094(14) 0.0684(5) Uani d . . . 1.000000 . .
Cl Cl2 0.82473(11) 0.83928(10) 0.22361(12) 0.0466(3) Uani d . . . 1.000000 . .
N N1 0.6711(3) 0.5734(3) 0.3019(3) 0.0278(7) Uani d . . . 1.000000 . .
N N2 0.5460(3) 0.7181(3) 0.3166(3) 0.0283(7) Uani d . . . 1.000000 . .
O O1 0.1070(3) 0.9349(3) 0.1482(3) 0.0545(9) Uani d . . . 1.000000 . .
H H1O 0.152302 0.915567 0.066508 0.082000 Uiso d U . R 1.000000 . .
H H2O 0.032796 0.891179 0.184640 0.082000 Uiso d U . R 1.000000 . .
O O2 0.0278(3) 0.1367(3) 0.0746(3) 0.0497(9) Uani d . . . 1.000000 . .
H H3O 0.039876 0.070506 0.116972 0.075000 Uiso d U . R 1.000000 . .
H H4O 0.059961 0.125420 -0.006039 0.075000 Uiso d U . R 1.000000 . .
O O3 0.7792(3) 0.0828(3) 0.1138(3) 0.0472(8) Uani d . . . 1.000000 . .
H H5O 0.776398 0.006344 0.130106 0.071000 Uiso d U . R 1.000000 . .
H H6O 0.849591 0.112960 0.113487 0.071000 Uiso d U . R 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.329(5) ?
C1 N1 . 1.336(5) ?
C1 C10 . 1.398(5) ?
C2 C3 . 1.387(6) ?
C2 N2 . 1.410(5) ?
C2 C22 . 1.480(6) ?
C3 N1 . 1.392(5) ?
C3 C28 . 1.475(5) ?
C4 N1 . 1.386(5) ?
C4 C5 . 1.396(5) ?
C4 C9 . 1.400(6) ?
C5 C6 . 1.391(6) ?
C5 C33 . 1.480(6) ?
C6 C7 . 1.398(6) ?
C7 C8 . 1.389(6) ?
C7 C34 . 1.537(8) ?
C7 C34A . 1.542(9) ?
C8 C9 . 1.401(6) ?
C9 C11 . 1.472(5) ?
C10 C15 . 1.405(5) ?
C10 C11 . 1.416(6) ?
C11 C12 . 1.393(6) ?
C12 C13 . 1.386(6) ?
C13 C14 . 1.382(6) ?
C14 C15 . 1.391(6) ?
C15 C17 . 1.464(6) ?
C16 C21 . 1.391(6) ?
C16 C17 . 1.421(6) ?
C16 N2 . 1.443(5) ?
C17 C18 . 1.404(6) ?
C18 C19 . 1.372(6) ?
C19 C20 . 1.381(6) ?
C20 C21 . 1.375(6) ?
C22 C23 . 1.383(6) ?
C22 C27 . 1.394(6) ?
C23 C24 . 1.382(6) ?
C24 C25 . 1.371(7) ?
C25 C26 . 1.389(6) ?
C26 C27 . 1.366(6) ?
C28 C29 . 1.407(6) ?
C28 C33 . 1.421(6) ?
C29 C30 . 1.376(6) ?
C29 Cl1 . 1.714(5) ?
C30 C31 . 1.357(7) ?
C31 C32 . 1.385(7) ?
C32 C33 . 1.397(6) ?
C34 C36 . 1.529(7) ?
C34 C37 . 1.529(7) ?
C34 C35 . 1.534(7) ?
C34A C37A . 1.532(8) ?
C34A C35A . 1.536(8) ?
C34A C36A . 1.536(8) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 109.5(3) ?
N2 C1 C10 . . 127.4(4) ?
N1 C1 C10 . . 123.1(4) ?
C3 C2 N2 . . 106.8(4) ?
C3 C2 C22 . . 132.9(4) ?
N2 C2 C22 . . 120.3(4) ?
C2 C3 N1 . . 105.9(3) ?
C2 C3 C28 . . 139.1(4) ?
N1 C3 C28 . . 115.1(4) ?
N1 C4 C5 . . 117.2(4) ?
N1 C4 C9 . . 119.0(3) ?
C5 C4 C9 . . 123.8(4) ?
C6 C5 C4 . . 116.6(4) ?
C6 C5 C33 . . 125.1(4) ?
C4 C5 C33 . . 118.2(4) ?
C5 C6 C7 . . 122.7(4) ?
C8 C7 C6 . . 118.0(4) ?
C8 C7 C34 . . 121.8(5) ?
C6 C7 C34 . . 120.3(5) ?
C8 C7 C34A . . 120.1(6) ?
C6 C7 C34A . . 121.4(5) ?
C7 C8 C9 . . 122.5(4) ?
C4 C9 C8 . . 116.5(4) ?
C4 C9 C11 . . 120.1(4) ?
C8 C9 C11 . . 123.4(4) ?
C1 C10 C15 . . 117.5(4) ?
C1 C10 C11 . . 118.7(3) ?
C15 C10 C11 . . 123.7(4) ?
C12 C11 C10 . . 116.9(4) ?
C12 C11 C9 . . 125.8(4) ?
C10 C11 C9 . . 117.3(4) ?
C13 C12 C11 . . 119.7(4) ?
C14 C13 C12 . . 122.8(4) ?
C13 C14 C15 . . 119.9(4) ?
C14 C15 C10 . . 117.0(4) ?
C14 C15 C17 . . 125.9(4) ?
C10 C15 C17 . . 117.1(4) ?
C21 C16 C17 . . 120.6(4) ?
C21 C16 N2 . . 122.3(4) ?
C17 C16 N2 . . 117.1(4) ?
C18 C17 C16 . . 116.9(4) ?
C18 C17 C15 . . 120.7(4) ?
C16 C17 C15 . . 122.2(4) ?
C19 C18 C17 . . 122.0(4) ?
C18 C19 C20 . . 119.8(4) ?
C21 C20 C19 . . 120.7(4) ?
C20 C21 C16 . . 120.0(4) ?
C23 C22 C27 . . 119.6(4) ?
C23 C22 C2 . . 120.4(4) ?
C27 C22 C2 . . 119.9(4) ?
C24 C23 C22 . . 119.7(4) ?
C25 C24 C23 . . 120.6(4) ?
C24 C25 C26 . . 119.7(4) ?
C27 C26 C25 . . 120.2(4) ?
C26 C27 C22 . . 120.1(4) ?
C29 C28 C33 . . 115.9(4) ?
C29 C28 C3 . . 126.4(4) ?
C33 C28 C3 . . 117.7(4) ?
C30 C29 C28 . . 122.8(5) ?
C30 C29 Cl1 . . 115.1(4) ?
C28 C29 Cl1 . . 121.9(3) ?
C31 C30 C29 . . 120.3(4) ?
C30 C31 C32 . . 119.5(4) ?
C31 C32 C33 . . 121.4(5) ?
C32 C33 C28 . . 119.7(4) ?
C32 C33 C5 . . 118.0(4) ?
C28 C33 C5 . . 122.3(4) ?
C36 C34 C37 . . 109.5(7) ?
C36 C34 C35 . . 108.3(8) ?
C37 C34 C35 . . 107.7(7) ?
C36 C34 C7 . . 105.8(7) ?
C37 C34 C7 . . 113.3(7) ?
C35 C34 C7 . . 112.1(6) ?
C37A C34A C35A . . 107.9(10) ?
C37A C34A C36A . . 108.7(9) ?
C35A C34A C36A . . 106.5(9) ?
C37A C34A C7 . . 108.9(10) ?
C35A C34A C7 . . 114.4(9) ?
C36A C34A C7 . . 110.4(9) ?
C1 N1 C4 . . 121.5(3) ?
C1 N1 C3 . . 109.5(3) ?
C4 N1 C3 . . 128.9(3) ?
C1 N2 C2 . . 108.2(3) ?
C1 N2 C16 . . 117.7(3) ?
C2 N2 C16 . . 133.6(4) ?

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2160759'
loop_
_audit_author_name
_audit_author_address
'Hiroyasu Sato'
;Rigaku
Japan
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'9-tert-butyl-14-chloro-15-phenyl-14b1,15a-diazadibenzo[fg,ij]cyclopenta[rst]pentaphenium chloride'
_chemical_formula_moiety         'F6 Sb, C37 H25 N2, 0.25(C6 H4 Cl2)'
_chemical_formula_sum            'C38.50 H26 Cl0.50 F6 N2 Sb'
_chemical_formula_weight         770.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Cl Sb F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 '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                   6.83820(10)
_cell_length_b                   31.9395(3)
_cell_length_c                   29.5549(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.5790(10)
_cell_angle_gamma                90
_cell_volume                     6452.60(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    34661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.1860
_cell_measurement_theta_min      2.0440
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.126
_exptl_absorpt_coefficient_mu    7.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.1a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3076
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 21 0 0.0116
0 -21 0 0.0116
4 0 1 0.2266
-4 0 -1 0.2266
0 0 -19 0.0171
0 0 19 0.0171

_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.023
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0540 20.7263 0.4125 -0.1805 0.9712 0.1555
-0.0540 -20.7263 -0.4125 0.1805 -0.9712 -0.1555
4.4196 -0.4503 1.1943 0.0291 -0.1604 0.9866
-4.4196 0.4503 -1.1943 -0.0291 0.1604 -0.9866
0.1144 0.2298 -19.1837 0.9812 0.1822 -0.0643
-0.1144 -0.2298 19.1837 -0.9812 -0.1822 0.0643

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            72021
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         2.037
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00 104.00   0.50    1.00    --   69.57   0.00 -60.00  132
  2  ω     62.00  87.00   0.50    1.00    --   69.57 162.00 113.00   50
  3  ω     58.00  83.00   0.50    1.00    --   65.22 162.00 113.00   50
  4  ω     31.00  99.00   0.50    1.00    --   65.22   0.00  30.00  136
  5  ω     31.00  56.00   0.50    1.00    --   65.22-117.00-124.00   50
  6  ω     34.00  96.00   0.50    1.00    --   69.57-125.00 -90.00  124
  7  ω     59.00  86.00   0.50    1.00    --   65.22-125.00 -30.00   54
  8  ω     25.00  89.00   0.50    1.00    --   65.22-125.00  30.00  128
  9  ω     47.00  72.00   0.50    1.00    --   65.22-162.00  85.00   50
 10  ω     51.00  76.00   0.50    1.00    --   69.57-162.00  85.00   50
 11  ω     36.00  61.00   0.50    1.00    --   69.57-117.00-124.00   50
 12  ω    -98.00 -71.00   0.50    1.00    --  -74.92   0.00  60.00   54
 13  ω    -97.00 -41.00   0.50    1.00    --  -65.40 162.00 113.00  112
 14  ω   -105.00 -80.00   0.50    1.00    --  -74.92 162.00 113.00   50
 15  ω   -108.00 -83.00   0.50    1.00    --  -78.67 162.00 113.00   50
 16  ω    -84.00 -39.00   0.50    1.00    --  -78.67 125.00 120.00   90
 17  ω    -88.00 -40.00   0.50    1.00    --  -65.40 125.00   0.00   96
 18  ω    -81.00 -39.00   0.50    1.00    --  -78.67 117.00 -36.00   84
 19  ω    -89.00 -64.00   0.50    1.00    --  -74.92 117.00 -36.00   50
 20  ω   -106.00 -40.00   0.50    1.00    --  -79.61 125.00 -91.92  132
 21  ω    -74.00 -49.00   0.50    1.00    --  -65.40 125.00-150.00   50
 22  ω   -105.00 -80.00   0.50    1.00    --  -79.61 123.00-151.79   50
 23  ω   -102.00 -39.00   0.50    1.00    --  -79.61 117.00-134.68  126
 24  ω   -102.00 -55.00   0.50    1.00    --  -79.61 117.00-118.79   94
 25  ω    -80.00 -55.00   0.50    1.00    --  -65.40 117.00 -36.00   50
 26  ω    -97.00 -37.00   0.50    1.00    --  -65.40 -15.00-120.00  120
 27  ω   -104.00 -37.00   0.50    1.00    --  -65.40 -15.00-180.00  134
 28  ω   -120.00 -50.00   0.50    1.00    --  -78.67 -15.00-150.00  140
 29  ω   -121.00 -50.00   0.50    1.00    --  -78.67 -15.00   0.00  142
 30  ω    -92.00 -66.00   0.50    1.00    --  -74.92-162.00  85.00   52
 31  ω   -108.00 -83.00   0.50    1.00    --  -78.67-162.00  85.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196013000
_diffrn_orient_matrix_UB_12      -0.0077426000
_diffrn_orient_matrix_UB_13      -0.0511212000
_diffrn_orient_matrix_UB_21      -0.0290222000
_diffrn_orient_matrix_UB_22      0.0471156000
_diffrn_orient_matrix_UB_23      -0.0091062000
_diffrn_orient_matrix_UB_31      0.2226458000
_diffrn_orient_matrix_UB_32      0.0068271000
_diffrn_orient_matrix_UB_33      0.0047631000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11241
_reflns_number_total             11746
_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       'CrysAlisPro 1.171.43.1a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.43.1a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.43.1a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.930
_refine_diff_density_min         -2.394
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     938
_refine_ls_number_reflns         11746
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0893
_refine_ls_restrained_S_all      1.158
_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)+(0.0815P)²+54.7320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2250
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C79 \\sim Cl1 \\sim C77 \\sim C76 \\sim C78 \\sim Cl2 \\sim C81 \\sim C80:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C34 \\sim C37 \\sim C35 \\sim C36 \\sim C36A \\sim C37A \\sim C35A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C78, Cl1, C77, C76, Cl2, C81, C79, C80
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C34, C37, C35, C36, C36A, C37A, C35A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C37A)=Sof(H37D)=Sof(H37E)=
 Sof(H37F)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
 Fixed Sof: Cl1(0.5) Cl2(0.5) C77(0.5) C76(0.5) C81(0.5) H81(0.5) C80(0.5)
 H80(0.5) C79(0.5) H79(0.5) C78(0.5) H78(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C32(H32), C60(H60), C45(H45), C43(H43), C30(H30), C31(H31), C6(H6),
 C12(H12), C8(H8), C49(H49), C24(H24), C14(H14), C58(H58), C67(H67), C26(H26),
 C21(H21), C69(H69), C18(H18), C63(H63), C25(H25), C13(H13), C20(H20), C51(H51),
  C61(H61), C62(H62), C68(H68), C19(H19), C55(H55), C57(H57), C50(H50),
 C56(H56), C81(H81), C80(H80), C79(H79), C78(H78)
5.b Idealised Me refined as rotating group:
 C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C72(H72A,H72B,H72C), C37(H37A,H37B,
 H37C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C36A(H36D,H36E,H36F),
 C37A(H37D,H37E,H37F), C35A(H35D,H35E,H35F)
;
_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
Sb1 Sb 0.26055(8) 0.56856(2) 0.74030(2) 0.0518(2) Uani 1 1 d . . . . .
Sb2 Sb 0.67462(12) 0.31173(2) 0.96306(2) 0.0585(2) Uani 1 1 d . . . . .
N1 N 0.7153(7) 0.36191(17) 0.70186(18) 0.0220(11) Uani 1 1 d . . . . .
N2 N 0.7014(8) 0.34141(17) 0.63106(18) 0.0230(11) Uani 1 1 d . . . . .
N3 N 1.2255(7) 0.26349(18) 0.71213(19) 0.0255(12) Uani 1 1 d . . . . .
N4 N 1.2048(8) 0.28438(18) 0.64138(19) 0.0267(12) Uani 1 1 d . . . . .
F6 F 0.2425(11) 0.58405(19) 0.8012(2) 0.082(2) Uani 1 1 d . . . . .
F10 F 0.6860(11) 0.26789(18) 1.00494(18) 0.0746(18) Uani 1 1 d . . . . .
F11 F 0.5034(11) 0.2804(2) 0.9262(2) 0.082(2) Uani 1 1 d . . . . .
F5 F 0.2789(11) 0.55367(19) 0.6793(2) 0.0786(19) Uani 1 1 d . . . . .
F3 F 0.2158(11) 0.62374(19) 0.7220(2) 0.084(2) Uani 1 1 d . . . . .
C2 C 0.7117(9) 0.30461(19) 0.6588(2) 0.0197(12) Uani 1 1 d . . . . .
C1 C 0.7003(8) 0.3751(2) 0.6592(2) 0.0215(13) Uani 1 1 d . . . . .
C3 C 0.7246(9) 0.3198(2) 0.7024(2) 0.0220(13) Uani 1 1 d . . . . .
F4 F 0.3080(12) 0.51386(19) 0.7577(2) 0.084(2) Uani 1 1 d . . . . .
C16 C 0.7136(9) 0.3505(2) 0.5831(2) 0.0236(13) Uani 1 1 d . . . . .
F1 F -0.0061(9) 0.5581(2) 0.7380(3) 0.088(2) Uani 1 1 d . . . . .
F9 F 0.6657(12) 0.3547(2) 0.9201(2) 0.083(2) Uani 1 1 d . . . . .
C40 C 1.2333(9) 0.3064(2) 0.7130(2) 0.0254(14) Uani 1 1 d . . . . .
C65 C 1.2423(9) 0.3280(2) 0.7537(2) 0.0289(15) Uani 1 1 d . . . . .
C10 C 0.6818(9) 0.4175(2) 0.6485(2) 0.0246(13) Uani 1 1 d . . . . .
C15 C 0.6627(9) 0.4274(2) 0.6026(2) 0.0262(14) Uani 1 1 d . . . . .
C29 C 0.7352(9) 0.2543(2) 0.7410(2) 0.0256(14) Uani 1 1 d . . . . .
C22 C 0.6938(9) 0.2596(2) 0.6545(2) 0.0247(13) Uani 1 1 d . . . . .
C39 C 1.2181(9) 0.3212(2) 0.6692(2) 0.0253(13) Uani 1 1 d . . . . .
C9 C 0.7128(10) 0.4311(2) 0.7321(2) 0.0284(14) Uani 1 1 d . . . . .
C38 C 1.2082(9) 0.2506(2) 0.6699(2) 0.0255(14) Uani 1 1 d . . . . .
F7 F 0.4680(12) 0.3365(2) 0.9929(2) 0.082(2) Uani 1 1 d . . . . .
C17 C 0.6817(9) 0.3934(2) 0.5697(2) 0.0240(13) Uani 1 1 d . . . . .
F12 F 0.8488(12) 0.3429(2) 0.9990(2) 0.085(2) Uani 1 1 d . . . . .
C41 C 1.2308(9) 0.2382(2) 0.7500(2) 0.0256(14) Uani 1 1 d . . . . .
C46 C 1.2162(9) 0.1948(2) 0.7426(2) 0.0270(14) Uani 1 1 d . . . . .
F8 F 0.8835(12) 0.2870(2) 0.9330(2) 0.088(2) Uani 1 1 d . . . . .
C53 C 1.2109(9) 0.2751(2) 0.5939(2) 0.0289(15) Uani 1 1 d . . . . .
C5 C 0.7435(9) 0.3679(2) 0.7821(2) 0.0267(14) Uani 1 1 d . . . . .
C27 C 0.7143(9) 0.2350(2) 0.6955(2) 0.0269(14) Uani 1 1 d . . . . .
C66 C 1.2398(9) 0.3715(2) 0.7509(3) 0.0337(16) Uani 1 1 d . . . . .
C28 C 0.7375(8) 0.2985(2) 0.7439(2) 0.0213(13) Uani 1 1 d . . . . .
C4 C 0.7253(9) 0.3880(2) 0.7394(2) 0.0250(14) Uani 1 1 d . . . . .
C23 C 0.6526(10) 0.2386(2) 0.6134(2) 0.0276(14) Uani 1 1 d . . . . .
H23 H 0.632899 0.254243 0.586348 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7470(10) 0.4390(2) 0.8139(2) 0.0309(15) Uani 1 1 d . . . . .
C11 C 0.6888(9) 0.4469(2) 0.6840(2) 0.0273(14) Uani 1 1 d . . . . .
C42 C 1.2455(10) 0.2581(2) 0.7925(2) 0.0311(15) Uani 1 1 d . . . . .
C33 C 0.7501(9) 0.3219(2) 0.7847(2) 0.0265(14) Uani 1 1 d . . . . .
C32 C 0.7608(10) 0.2983(2) 0.8247(2) 0.0300(15) Uani 1 1 d . . . . .
H32 H 0.768175 0.311925 0.853308 0.036 Uiso 1 1 calc R U . . .
C60 C 1.1536(10) 0.3868(2) 0.6236(3) 0.0353(16) Uani 1 1 d . . . . .
H60 H 1.129145 0.370677 0.597046 0.042 Uiso 1 1 calc R U . . .
C45 C 1.2247(11) 0.1698(2) 0.7813(2) 0.0330(16) Uani 1 1 d . . . . .
H45 H 1.219601 0.140182 0.778294 0.040 Uiso 1 1 calc R U . . .
C48 C 1.1932(10) 0.1788(2) 0.6955(2) 0.0307(15) Uani 1 1 d . . . . .
C59 C 1.1993(9) 0.3658(2) 0.6641(3) 0.0304(15) Uani 1 1 d . . . . .
C52 C 1.1566(10) 0.1981(2) 0.6128(2) 0.0316(15) Uani 1 1 d . . . . .
C43 C 1.2538(9) 0.2308(2) 0.8295(2) 0.0319(16) Uani 1 1 d . . . . .
H43 H 1.268981 0.242284 0.859036 0.038 Uiso 1 1 calc R U . . .
C64 C 1.2170(10) 0.3903(2) 0.7052(3) 0.0346(16) Uani 1 1 d . . . . .
C30 C 0.7476(10) 0.2326(2) 0.7824(2) 0.0315(15) Uani 1 1 d . . . . .
H30 H 0.747198 0.202822 0.783019 0.038 Uiso 1 1 calc R U . . .
F2 F 0.5303(10) 0.5782(3) 0.7429(3) 0.106(3) Uani 1 1 d . . . . .
C47 C 1.1866(10) 0.2089(2) 0.6589(2) 0.0302(15) Uani 1 1 d . . . . .
C31 C 0.7604(9) 0.2553(2) 0.8223(2) 0.0308(15) Uani 1 1 d . . . . .
H31 H 0.769487 0.240142 0.849937 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7552(10) 0.3956(2) 0.8190(2) 0.0301(15) Uani 1 1 d . . . . .
H6 H 0.769261 0.384365 0.848654 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6659(11) 0.4885(2) 0.6727(3) 0.0345(16) Uani 1 1 d . . . . .
H12 H 0.665924 0.509532 0.695415 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7242(11) 0.4565(2) 0.7705(3) 0.0345(16) Uani 1 1 d . . . . .
H8 H 0.716316 0.486024 0.767205 0.041 Uiso 1 1 calc R U . . .
C44 C 1.2409(10) 0.1878(3) 0.8247(2) 0.0328(16) Uani 1 1 d . . . . .
C70 C 1.2554(10) 0.3044(2) 0.7952(2) 0.0321(15) Uani 1 1 d . . . . .
C54 C 1.1722(11) 0.2334(3) 0.5805(2) 0.0358(16) Uani 1 1 d . . . . .
C49 C 1.1715(11) 0.1379(2) 0.6833(3) 0.0353(16) Uani 1 1 d . . . . .
H49 H 1.179102 0.116606 0.705718 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6406(10) 0.1956(2) 0.6120(2) 0.0298(15) Uani 1 1 d . . . . .
H24 H 0.613018 0.182010 0.583909 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6421(10) 0.4700(2) 0.5928(3) 0.0322(15) Uani 1 1 d . . . . .
H14 H 0.627406 0.478926 0.562264 0.039 Uiso 1 1 calc R U . . .
C58 C 1.2675(10) 0.3048(3) 0.5623(3) 0.0365(17) Uani 1 1 d . . . . .
H58 H 1.308117 0.331764 0.572267 0.044 Uiso 1 1 calc R U . . .
C67 C 1.2536(11) 0.3933(3) 0.7915(3) 0.0401(18) Uani 1 1 d . . . . .
H67 H 1.254066 0.423046 0.791495 0.048 Uiso 1 1 calc R U . . .
C26 C 0.7037(10) 0.1913(2) 0.6914(2) 0.0311(15) Uani 1 1 d . . . . .
H26 H 0.722123 0.174683 0.717777 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7687(10) 0.3211(2) 0.5515(2) 0.0292(14) Uani 1 1 d . . . . .
H21 H 0.803671 0.293679 0.561133 0.035 Uiso 1 1 calc R U . . .
C69 C 1.2688(10) 0.3280(3) 0.8344(3) 0.0359(17) Uani 1 1 d . . . . .
H69 H 1.279394 0.314441 0.863042 0.043 Uiso 1 1 calc R U . . .
C18 C 0.6902(11) 0.4019(2) 0.5239(2) 0.0322(15) Uani 1 1 d . . . . .
H18 H 0.667009 0.429752 0.513744 0.039 Uiso 1 1 calc R U . . .
C63 C 1.2072(11) 0.4345(2) 0.7000(3) 0.0407(19) Uani 1 1 d . . . . .
H63 H 1.224609 0.451502 0.726173 0.049 Uiso 1 1 calc R U . . .
C25 C 0.6682(11) 0.1718(2) 0.6510(3) 0.0346(16) Uani 1 1 d . . . . .
H25 H 0.662294 0.142158 0.649512 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6428(11) 0.4992(2) 0.6269(3) 0.0365(17) Uani 1 1 d . . . . .
H13 H 0.626887 0.527849 0.619124 0.044 Uiso 1 1 calc R U . . .
C20 C 0.7735(10) 0.3310(2) 0.5067(2) 0.0338(16) Uani 1 1 d . . . . .
H20 H 0.805875 0.310073 0.485294 0.041 Uiso 1 1 calc R U . . .
C51 C 1.1310(12) 0.1562(3) 0.6032(3) 0.0404(18) Uani 1 1 d . . . . .
H51 H 1.108557 0.147432 0.572787 0.048 Uiso 1 1 calc R U . . .
C61 C 1.1427(11) 0.4290(3) 0.6206(3) 0.044(2) Uani 1 1 d . . . . .
H61 H 1.114010 0.442031 0.592258 0.053 Uiso 1 1 calc R U . . .
C62 C 1.1743(11) 0.4534(3) 0.6597(3) 0.045(2) Uani 1 1 d . . . . .
H62 H 1.172508 0.483085 0.657742 0.054 Uiso 1 1 calc R U . . .
C71 C 1.2484(13) 0.1604(3) 0.8671(3) 0.0425(19) Uani 1 1 d . . . . .
C34 C 0.7558(14) 0.4679(3) 0.8558(3) 0.0472(18) Uani 1 1 d . U . . .
C68 C 1.2666(11) 0.3716(3) 0.8320(3) 0.0430(19) Uani 1 1 d . . . . .
H68 H 1.274530 0.387170 0.859391 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7314(11) 0.3714(2) 0.4922(2) 0.0342(16) Uani 1 1 d . . . . .
H19 H 0.730805 0.378034 0.460844 0.041 Uiso 1 1 calc R U . . .
C55 C 1.1645(13) 0.2252(3) 0.5336(3) 0.0444(19) Uani 1 1 d . . . . .
H55 H 1.127866 0.198050 0.523265 0.053 Uiso 1 1 calc R U . . .
C73 C 1.0711(13) 0.1714(3) 0.8958(3) 0.045(2) Uani 1 1 d . . . . .
H73A H 1.070244 0.201515 0.901877 0.068 Uiso 1 1 calc R U . . .
H73B H 1.079672 0.156010 0.924496 0.068 Uiso 1 1 calc R U . . .
H73C H 0.950373 0.163519 0.879267 0.068 Uiso 1 1 calc R U . . .
C57 C 1.2652(12) 0.2955(3) 0.5171(3) 0.0437(19) Uani 1 1 d . . . . .
H57 H 1.301634 0.316000 0.495677 0.052 Uiso 1 1 calc R U . . .
C50 C 1.1379(13) 0.1269(3) 0.6374(3) 0.0444(19) Uani 1 1 d . . . . .
H50 H 1.119250 0.098229 0.629905 0.053 Uiso 1 1 calc R U . . .
C56 C 1.2088(14) 0.2555(3) 0.5027(3) 0.051(2) Uani 1 1 d . . . . .
H56 H 1.201120 0.249298 0.471316 0.061 Uiso 1 1 calc R U . . .
C74 C 1.4410(13) 0.1704(4) 0.8947(3) 0.063(3) Uani 1 1 d . . . . .
H74A H 1.554010 0.163068 0.876621 0.094 Uiso 1 1 calc R U . . .
H74B H 1.444457 0.154036 0.922770 0.094 Uiso 1 1 calc R U . . .
H74C H 1.445192 0.200303 0.901992 0.094 Uiso 1 1 calc R U . . .
C72 C 1.237(2) 0.1135(3) 0.8569(3) 0.076(4) Uani 1 1 d . . . . .
H72A H 1.116916 0.107468 0.839312 0.114 Uiso 1 1 calc R U . . .
H72B H 1.237242 0.097737 0.885322 0.114 Uiso 1 1 calc R U . . .
H72C H 1.350712 0.105199 0.839374 0.114 Uiso 1 1 calc R U . . .
C37 C 0.592(2) 0.4570(4) 0.8869(4) 0.057(3) Uani 0.801(11) 1 d . U P A 1
H37A H 0.466662 0.465973 0.873038 0.085 Uiso 0.801(11) 1 calc R U P A 1
H37B H 0.612387 0.471352 0.915946 0.085 Uiso 0.801(11) 1 calc R U P A 1
H37C H 0.589266 0.426685 0.891854 0.085 Uiso 0.801(11) 1 calc R U P A 1
C35 C 0.744(3) 0.5138(4) 0.8441(4) 0.065(3) Uani 0.801(11) 1 d . U P A 1
H35A H 0.860756 0.522020 0.827779 0.098 Uiso 0.801(11) 1 calc R U P A 1
H35B H 0.736674 0.530298 0.872025 0.098 Uiso 0.801(11) 1 calc R U P A 1
H35C H 0.627122 0.519013 0.825053 0.098 Uiso 0.801(11) 1 calc R U P A 1
C36 C 0.955(2) 0.4577(4) 0.8823(4) 0.065(3) Uani 0.801(11) 1 d . U P A 1
H36A H 0.944299 0.430374 0.897219 0.098 Uiso 0.801(11) 1 calc R U P A 1
H36B H 0.980988 0.479348 0.905127 0.098 Uiso 0.801(11) 1 calc R U P A 1
H36C H 1.061795 0.456938 0.860963 0.098 Uiso 0.801(11) 1 calc R U P A 1
Cl1 Cl 0.8712(9) 0.46875(19) 0.43261(19) 0.0650(13) Uani 0.5 1 d . U P B -1
Cl2 Cl 1.2414(9) 0.44759(19) 0.4947(2) 0.0723(15) Uani 0.5 1 d . U P B -1
C77 C 0.926(6) 0.5003(8) 0.4830(12) 0.054(5) Uani 0.5 1 d . U P B -1
C76 C 1.088(7) 0.4856(10) 0.5080(13) 0.067(6) Uani 0.5 1 d . U P B -1
C81 C 1.135(4) 0.5109(8) 0.5419(10) 0.067(5) Uani 0.5 1 d . U P B -1
H81 H 1.256136 0.506748 0.558000 0.081 Uiso 0.5 1 calc R U P B -1
C80 C 1.002(4) 0.5467(8) 0.5563(9) 0.072(5) Uani 0.5 1 d . U P B -1
H80 H 1.030773 0.561703 0.583415 0.087 Uiso 0.5 1 calc R U P B -1
C79 C 0.861(4) 0.5559(8) 0.5333(9) 0.078(6) Uani 0.5 1 d . U P B -1
H79 H 0.792339 0.580977 0.539437 0.093 Uiso 0.5 1 calc R U P B -1
C78 C 0.785(5) 0.5250(9) 0.4902(7) 0.083(6) Uani 0.5 1 d . U P B -1
H78 H 0.661635 0.525800 0.474597 0.100 Uiso 0.5 1 calc R U P B -1
C36A C 0.954(8) 0.4946(15) 0.8516(15) 0.055(5) Uani 0.199(11) 1 d . U P A 2
H36D H 1.066078 0.477570 0.861894 0.083 Uiso 0.199(11) 1 calc R U P A 2
H36E H 0.946629 0.519825 0.870275 0.083 Uiso 0.199(11) 1 calc R U P A 2
H36F H 0.970850 0.502617 0.819884 0.083 Uiso 0.199(11) 1 calc R U P A 2
C37A C 0.764(8) 0.4450(16) 0.8984(15) 0.056(5) Uani 0.199(11) 1 d . U P A 2
H37D H 0.694174 0.418381 0.894724 0.084 Uiso 0.199(11) 1 calc R U P A 2
H37E H 0.701803 0.461734 0.921864 0.084 Uiso 0.199(11) 1 calc R U P A 2
H37F H 0.900493 0.439640 0.907315 0.084 Uiso 0.199(11) 1 calc R U P A 2
C35A C 0.608(9) 0.5027(16) 0.8520(17) 0.058(5) Uani 0.199(11) 1 d . U P A 2
H35D H 0.601700 0.513193 0.820818 0.087 Uiso 0.199(11) 1 calc R U P A 2
H35E H 0.646323 0.525521 0.872561 0.087 Uiso 0.199(11) 1 calc R U P A 2
H35F H 0.478859 0.492126 0.860116 0.087 Uiso 0.199(11) 1 calc R 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
Sb1 F6 1.873(6) . ?
Sb1 F5 1.871(6) . ?
Sb1 F3 1.866(6) . ?
Sb1 F4 1.848(6) . ?
Sb1 F1 1.853(6) . ?
Sb1 F2 1.870(7) . ?
Sb2 F10 1.869(5) . ?
Sb2 F11 1.867(6) . ?
Sb2 F9 1.869(6) . ?
Sb2 F7 1.862(7) . ?
Sb2 F12 1.862(7) . ?
Sb2 F8 1.878(7) . ?
N1 C1 1.331(8) . ?
N1 C3 1.345(8) . ?
N1 C4 1.386(8) . ?
N2 C2 1.434(8) . ?
N2 C1 1.359(8) . ?
N2 C16 1.450(8) . ?
N3 C40 1.371(9) . ?
N3 C38 1.317(9) . ?
N3 C41 1.382(9) . ?
N4 C39 1.437(9) . ?
N4 C38 1.369(9) . ?
N4 C53 1.437(9) . ?
C2 C3 1.376(9) . ?
C2 C22 1.448(9) . ?
C1 C10 1.397(9) . ?
C3 C28 1.403(9) . ?
C16 C17 1.440(9) . ?
C16 C21 1.386(10) . ?
C40 C65 1.386(10) . ?
C40 C39 1.380(9) . ?
C65 C66 1.392(10) . ?
C65 C70 1.441(10) . ?
C10 C15 1.396(9) . ?
C10 C11 1.406(10) . ?
C15 C17 1.465(10) . ?
C15 C14 1.399(10) . ?
C29 C27 1.483(9) . ?
C29 C28 1.415(9) . ?
C29 C30 1.409(10) . ?
C22 C27 1.448(9) . ?
C22 C23 1.410(9) . ?
C39 C59 1.437(10) . ?
C9 C4 1.395(10) . ?
C9 C11 1.513(10) . ?
C9 C8 1.396(10) . ?
C38 C47 1.377(10) . ?
C17 C18 1.386(9) . ?
C41 C46 1.405(10) . ?
C41 C42 1.407(10) . ?
C46 C45 1.396(10) . ?
C46 C48 1.486(10) . ?
C53 C54 1.413(11) . ?
C53 C58 1.391(10) . ?
C5 C4 1.419(10) . ?
C5 C33 1.473(10) . ?
C5 C6 1.405(10) . ?
C27 C26 1.402(10) . ?
C66 C64 1.483(11) . ?
C66 C67 1.387(11) . ?
C28 C33 1.418(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(10) . ?
C7 C6 1.395(10) . ?
C7 C8 1.404(11) . ?
C7 C34 1.543(10) . ?
C11 C12 1.380(10) . ?
C42 C43 1.398(10) . ?
C42 C70 1.482(11) . ?
C33 C32 1.404(10) . ?
C32 H32 0.9500 . ?
C32 C31 1.375(11) . ?
C60 H60 0.9500 . ?
C60 C59 1.400(10) . ?
C60 C61 1.353(11) . ?
C45 H45 0.9500 . ?
C45 C44 1.408(10) . ?
C48 C47 1.450(10) . ?
C48 C49 1.362(11) . ?
C59 C64 1.447(11) . ?
C52 C47 1.414(10) . ?
C52 C54 1.485(10) . ?
C52 C51 1.378(11) . ?
C43 H43 0.9500 . ?
C43 C44 1.384(11) . ?
C64 C63 1.420(11) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(10) . ?
C31 H31 0.9500 . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.398(11) . ?
C8 H8 0.9500 . ?
C44 C71 1.529(10) . ?
C70 C69 1.384(10) . ?
C54 C55 1.408(11) . ?
C49 H49 0.9500 . ?
C49 C50 1.413(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(10) . ?
C14 H14 0.9500 . ?
C14 C13 1.371(11) . ?
C58 H58 0.9500 . ?
C58 C57 1.369(11) . ?
C67 H67 0.9500 . ?
C67 C68 1.383(12) . ?
C26 H26 0.9500 . ?
C26 C25 1.362(11) . ?
C21 H21 0.9500 . ?
C21 C20 1.361(10) . ?
C69 H69 0.9500 . ?
C69 C68 1.397(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(10) . ?
C63 H63 0.9500 . ?
C63 C62 1.350(12) . ?
C25 H25 0.9500 . ?
C13 H13 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.388(11) . ?
C51 H51 0.9500 . ?
C51 C50 1.377(12) . ?
C61 H61 0.9500 . ?
C61 C62 1.406(13) . ?
C62 H62 0.9500 . ?
C71 C73 1.539(11) . ?
C71 C74 1.562(13) . ?
C71 C72 1.530(13) . ?
C34 C37 1.510(14) . ?
C34 C35 1.510(15) . ?
C34 C36 1.584(16) . ?
C34 C36A 1.61(5) . ?
C34 C37A 1.45(5) . ?
C34 C35A 1.51(5) . ?
C68 H68 0.9500 . ?
C19 H19 0.9500 . ?
C55 H55 0.9500 . ?
C55 C56 1.372(12) . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C57 H57 0.9500 . ?
C57 C56 1.395(13) . ?
C50 H50 0.9500 . ?
C56 H56 0.9500 . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cl1 C77 1.83(4) . ?
Cl2 C76 1.66(4) . ?
C77 C76 1.40(3) . ?
C77 C78 1.27(5) . ?
C76 C81 1.32(4) . ?
C81 H81 0.9500 . ?
C81 C80 1.53(3) . ?
C80 H80 0.9500 . ?
C80 C79 1.20(3) . ?
C79 H79 0.9500 . ?
C79 C78 1.68(4) . ?
C78 H78 0.9500 . ?
C36A H36D 0.9800 . ?
C36A H36E 0.9800 . ?
C36A H36F 0.9800 . ?
C37A H37D 0.9800 . ?
C37A H37E 0.9800 . ?
C37A H37F 0.9800 . ?
C35A H35D 0.9800 . ?
C35A H35E 0.9800 . ?
C35A H35F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5 Sb1 F6 179.4(3) . . ?
F3 Sb1 F6 90.8(3) . . ?
F3 Sb1 F5 88.6(3) . . ?
F3 Sb1 F2 90.6(4) . . ?
F4 Sb1 F6 89.8(3) . . ?
F4 Sb1 F5 90.7(3) . . ?
F4 Sb1 F3 179.1(4) . . ?
F4 Sb1 F1 90.3(4) . . ?
F4 Sb1 F2 88.8(4) . . ?
F1 Sb1 F6 89.6(3) . . ?
F1 Sb1 F5 90.6(3) . . ?
F1 Sb1 F3 90.3(3) . . ?
F1 Sb1 F2 179.1(4) . . ?
F2 Sb1 F6 90.5(4) . . ?
F2 Sb1 F5 89.3(4) . . ?
F10 Sb2 F9 178.6(3) . . ?
F10 Sb2 F8 88.8(3) . . ?
F11 Sb2 F10 89.9(3) . . ?
F11 Sb2 F9 89.4(3) . . ?
F11 Sb2 F8 88.4(4) . . ?
F9 Sb2 F8 89.9(3) . . ?
F7 Sb2 F10 91.4(3) . . ?
F7 Sb2 F11 91.8(3) . . ?
F7 Sb2 F9 89.9(3) . . ?
F7 Sb2 F12 89.1(3) . . ?
F7 Sb2 F8 179.7(4) . . ?
F12 Sb2 F10 90.5(3) . . ?
F12 Sb2 F11 179.0(3) . . ?
F12 Sb2 F9 90.2(3) . . ?
F12 Sb2 F8 90.7(4) . . ?
C1 N1 C3 109.2(5) . . ?
C1 N1 C4 124.7(6) . . ?
C3 N1 C4 126.1(6) . . ?
C2 N2 C16 136.1(5) . . ?
C1 N2 C2 107.4(5) . . ?
C1 N2 C16 116.1(5) . . ?
C40 N3 C41 124.7(6) . . ?
C38 N3 C40 109.5(6) . . ?
C38 N3 C41 125.8(6) . . ?
C39 N4 C53 136.5(6) . . ?
C38 N4 C39 107.1(5) . . ?
C38 N4 C53 116.0(6) . . ?
N2 C2 C22 139.4(6) . . ?
C3 C2 N2 104.3(5) . . ?
C3 C2 C22 115.9(6) . . ?
N1 C1 N2 109.1(6) . . ?
N1 C1 C10 121.6(6) . . ?
N2 C1 C10 129.2(6) . . ?
N1 C3 C2 109.9(6) . . ?
N1 C3 C28 119.7(6) . . ?
C2 C3 C28 130.3(6) . . ?
C17 C16 N2 116.5(6) . . ?
C21 C16 N2 123.2(6) . . ?
C21 C16 C17 120.0(6) . . ?
N3 C40 C65 121.0(6) . . ?
N3 C40 C39 108.8(6) . . ?
C39 C40 C65 130.0(7) . . ?
C40 C65 C66 116.6(7) . . ?
C40 C65 C70 118.5(7) . . ?
C66 C65 C70 124.9(7) . . ?
C1 C10 C11 118.6(6) . . ?
C15 C10 C1 116.3(6) . . ?
C15 C10 C11 125.1(6) . . ?
C10 C15 C17 118.0(6) . . ?
C10 C15 C14 115.2(6) . . ?
C14 C15 C17 126.6(6) . . ?
C28 C29 C27 118.1(6) . . ?
C30 C29 C27 125.8(6) . . ?
C30 C29 C28 116.1(6) . . ?
C2 C22 C27 117.3(6) . . ?
C23 C22 C2 124.4(6) . . ?
C23 C22 C27 118.3(6) . . ?
N4 C39 C59 138.3(6) . . ?
C40 C39 N4 105.0(6) . . ?
C40 C39 C59 116.3(6) . . ?
C4 C9 C11 118.6(6) . . ?
C4 C9 C8 116.5(7) . . ?
C8 C9 C11 124.9(7) . . ?
N3 C38 N4 109.6(6) . . ?
N3 C38 C47 122.2(6) . . ?
N4 C38 C47 128.1(6) . . ?
C16 C17 C15 122.6(6) . . ?
C18 C17 C16 116.5(6) . . ?
C18 C17 C15 120.6(6) . . ?
N3 C41 C46 116.7(6) . . ?
N3 C41 C42 117.2(6) . . ?
C46 C41 C42 126.1(6) . . ?
C41 C46 C48 119.5(6) . . ?
C45 C46 C41 115.8(6) . . ?
C45 C46 C48 124.7(7) . . ?
C54 C53 N4 117.2(6) . . ?
C58 C53 N4 122.0(7) . . ?
C58 C53 C54 120.5(7) . . ?
C4 C5 C33 119.9(6) . . ?
C6 C5 C4 114.1(6) . . ?
C6 C5 C33 126.1(6) . . ?
C22 C27 C29 122.5(6) . . ?
C26 C27 C29 119.8(6) . . ?
C26 C27 C22 117.6(6) . . ?
C65 C66 C64 117.2(7) . . ?
C67 C66 C65 116.7(8) . . ?
C67 C66 C64 126.0(7) . . ?
C3 C28 C29 115.5(6) . . ?
C3 C28 C33 119.3(6) . . ?
C29 C28 C33 125.2(6) . . ?
N1 C4 C9 117.9(6) . . ?
N1 C4 C5 116.2(6) . . ?
C9 C4 C5 125.9(6) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.9(6) . . ?
C24 C23 H23 119.6 . . ?
C6 C7 C8 119.7(6) . . ?
C6 C7 C34 120.4(7) . . ?
C8 C7 C34 119.8(7) . . ?
C10 C11 C9 118.6(6) . . ?
C12 C11 C10 117.4(6) . . ?
C12 C11 C9 124.0(7) . . ?
C41 C42 C70 120.1(6) . . ?
C43 C42 C41 114.6(7) . . ?
C43 C42 C70 125.3(7) . . ?
C28 C33 C5 118.7(6) . . ?
C32 C33 C5 125.4(6) . . ?
C32 C33 C28 115.8(6) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 C33 119.5(7) . . ?
C31 C32 H32 120.3 . . ?
C59 C60 H60 118.5 . . ?
C61 C60 H60 118.5 . . ?
C61 C60 C59 123.0(8) . . ?
C46 C45 H45 119.6 . . ?
C46 C45 C44 120.9(7) . . ?
C44 C45 H45 119.6 . . ?
C47 C48 C46 118.0(6) . . ?
C49 C48 C46 126.0(7) . . ?
C49 C48 C47 115.9(7) . . ?
C39 C59 C64 116.3(7) . . ?
C60 C59 C39 125.5(7) . . ?
C60 C59 C64 118.0(7) . . ?
C47 C52 C54 115.0(7) . . ?
C51 C52 C47 116.7(7) . . ?
C51 C52 C54 128.1(7) . . ?
C42 C43 H43 118.8 . . ?
C44 C43 C42 122.5(7) . . ?
C44 C43 H43 118.8 . . ?
C59 C64 C66 123.4(7) . . ?
C63 C64 C66 120.2(7) . . ?
C63 C64 C59 116.3(7) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.8(7) . . ?
C31 C30 H30 120.6 . . ?
C38 C47 C48 117.7(6) . . ?
C38 C47 C52 118.4(6) . . ?
C52 C47 C48 123.9(7) . . ?
C32 C31 C30 124.6(7) . . ?
C32 C31 H31 117.7 . . ?
C30 C31 H31 117.7 . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.8(7) . . ?
C7 C6 H6 118.6 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.6(7) . . ?
C13 C12 H12 120.7 . . ?
C9 C8 C7 121.0(7) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C45 C44 C71 120.9(7) . . ?
C43 C44 C45 120.1(7) . . ?
C43 C44 C71 118.9(7) . . ?
C65 C70 C42 118.3(6) . . ?
C69 C70 C65 115.5(7) . . ?
C69 C70 C42 126.1(7) . . ?
C53 C54 C52 123.5(6) . . ?
C55 C54 C53 117.0(7) . . ?
C55 C54 C52 119.3(7) . . ?
C48 C49 H49 119.8 . . ?
C48 C49 C50 120.5(7) . . ?
C50 C49 H49 119.8 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(7) . . ?
C25 C24 H24 119.6 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.8(7) . . ?
C13 C14 H14 119.6 . . ?
C53 C58 H58 119.7 . . ?
C57 C58 C53 120.7(8) . . ?
C57 C58 H58 119.7 . . ?
C66 C67 H67 120.1 . . ?
C68 C67 C66 119.9(8) . . ?
C68 C67 H67 120.1 . . ?
C27 C26 H26 118.7 . . ?
C25 C26 C27 122.6(7) . . ?
C25 C26 H26 118.7 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.9(7) . . ?
C20 C21 H21 119.5 . . ?
C70 C69 H69 120.0 . . ?
C70 C69 C68 119.9(8) . . ?
C68 C69 H69 120.0 . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.5(7) . . ?
C19 C18 H18 118.8 . . ?
C64 C63 H63 118.4 . . ?
C62 C63 C64 123.1(8) . . ?
C62 C63 H63 118.4 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(7) . . ?
C26 C25 H25 120.2 . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.9(7) . . ?
C14 C13 H13 118.6 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.4(7) . . ?
C19 C20 H20 119.8 . . ?
C52 C51 H51 119.8 . . ?
C50 C51 C52 120.4(7) . . ?
C50 C51 H51 119.8 . . ?
C60 C61 H61 120.3 . . ?
C60 C61 C62 119.4(8) . . ?
C62 C61 H61 120.3 . . ?
C63 C62 C61 119.7(8) . . ?
C63 C62 H62 120.1 . . ?
C61 C62 H62 120.1 . . ?
C44 C71 C73 108.2(6) . . ?
C44 C71 C74 108.7(7) . . ?
C44 C71 C72 113.4(7) . . ?
C73 C71 C74 109.4(7) . . ?
C72 C71 C73 107.2(8) . . ?
C72 C71 C74 109.9(8) . . ?
C7 C34 C36 106.7(8) . . ?
C7 C34 C36A 105.5(15) . . ?
C37 C34 C7 109.7(7) . . ?
C37 C34 C36 107.1(9) . . ?
C35 C34 C7 113.3(8) . . ?
C35 C34 C37 109.0(10) . . ?
C35 C34 C36 110.7(10) . . ?
C37A C34 C7 113.3(19) . . ?
C37A C34 C36A 109(3) . . ?
C37A C34 C35A 116(3) . . ?
C35A C34 C7 111.7(19) . . ?
C35A C34 C36A 100(3) . . ?
C67 C68 C69 123.0(7) . . ?
C67 C68 H68 118.5 . . ?
C69 C68 H68 118.5 . . ?
C18 C19 C20 119.3(6) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C54 C55 H55 119.4 . . ?
C56 C55 C54 121.3(8) . . ?
C56 C55 H55 119.4 . . ?
C71 C73 H73A 109.5 . . ?
C71 C73 H73B 109.5 . . ?
C71 C73 H73C 109.5 . . ?
H73A C73 H73B 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C58 C57 H57 120.3 . . ?
C58 C57 C56 119.4(8) . . ?
C56 C57 H57 120.3 . . ?
C49 C50 H50 118.8 . . ?
C51 C50 C49 122.5(7) . . ?
C51 C50 H50 118.8 . . ?
C55 C56 C57 120.5(8) . . ?
C55 C56 H56 119.7 . . ?
C57 C56 H56 119.7 . . ?
C71 C74 H74A 109.5 . . ?
C71 C74 H74B 109.5 . . ?
C71 C74 H74C 109.5 . . ?
H74A C74 H74B 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72B 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C76 C77 Cl1 113(2) . . ?
C78 C77 Cl1 110(3) . . ?
C78 C77 C76 136(3) . . ?
C77 C76 Cl2 128(3) . . ?
C81 C76 Cl2 119(3) . . ?
C81 C76 C77 112(3) . . ?
C76 C81 H81 118.9 . . ?
C76 C81 C80 122(3) . . ?
C80 C81 H81 118.9 . . ?
C81 C80 H80 120.0 . . ?
C79 C80 C81 120(3) . . ?
C79 C80 H80 120.0 . . ?
C80 C79 H79 119.6 . . ?
C80 C79 C78 121(2) . . ?
C78 C79 H79 119.6 . . ?
C77 C78 C79 106(3) . . ?
C77 C78 H78 127.2 . . ?
C79 C78 H78 127.2 . . ?
C34 C36A H36D 109.5 . . ?
C34 C36A H36E 109.5 . . ?
C34 C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
C34 C37A H37D 109.5 . . ?
C34 C37A H37E 109.5 . . ?
C34 C37A H37F 109.5 . . ?
H37D C37A H37E 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
C34 C35A H35D 109.5 . . ?
C34 C35A H35E 109.5 . . ?
C34 C35A H35F 109.5 . . ?
H35D C35A H35E 109.5 . . ?
H35D C35A H35F 109.5 . . ?
H35E C35A H35F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C10 C15 -178.6(6) . . . . ?
N1 C1 C10 C11 3.0(9) . . . . ?
N1 C3 C28 C29 176.5(5) . . . . ?
N1 C3 C28 C33 -3.0(9) . . . . ?
N2 C2 C3 N1 2.2(7) . . . . ?
N2 C2 C3 C28 179.6(6) . . . . ?
N2 C2 C22 C27 -178.7(7) . . . . ?
N2 C2 C22 C23 -0.6(12) . . . . ?
N2 C1 C10 C15 -0.4(10) . . . . ?
N2 C1 C10 C11 -178.8(6) . . . . ?
N2 C16 C17 C15 7.6(9) . . . . ?
N2 C16 C17 C18 -179.0(6) . . . . ?
N2 C16 C21 C20 178.5(6) . . . . ?
N3 C40 C65 C66 -176.9(6) . . . . ?
N3 C40 C65 C70 3.7(9) . . . . ?
N3 C40 C39 N4 -1.2(7) . . . . ?
N3 C40 C39 C59 172.6(5) . . . . ?
N3 C38 C47 C48 -3.0(10) . . . . ?
N3 C38 C47 C52 176.0(6) . . . . ?
N3 C41 C46 C45 179.1(6) . . . . ?
N3 C41 C46 C48 -0.9(9) . . . . ?
N3 C41 C42 C43 -178.9(6) . . . . ?
N3 C41 C42 C70 -0.3(9) . . . . ?
N4 C39 C59 C60 0.8(12) . . . . ?
N4 C39 C59 C64 176.6(7) . . . . ?
N4 C38 C47 C48 -179.2(6) . . . . ?
N4 C38 C47 C52 -0.1(11) . . . . ?
N4 C53 C54 C52 -9.8(10) . . . . ?
N4 C53 C54 C55 175.6(6) . . . . ?
N4 C53 C58 C57 -177.7(7) . . . . ?
C2 N2 C1 N1 1.9(6) . . . . ?
C2 N2 C1 C10 -176.4(6) . . . . ?
C2 N2 C16 C17 176.1(6) . . . . ?
C2 N2 C16 C21 -9.2(11) . . . . ?
C2 C3 C28 C29 -0.7(10) . . . . ?
C2 C3 C28 C33 179.8(6) . . . . ?
C2 C22 C27 C29 5.3(9) . . . . ?
C2 C22 C27 C26 -177.9(6) . . . . ?
C2 C22 C23 C24 179.1(6) . . . . ?
C1 N1 C3 C2 -1.1(7) . . . . ?
C1 N1 C3 C28 -178.8(5) . . . . ?
C1 N1 C4 C9 2.0(9) . . . . ?
C1 N1 C4 C5 -179.2(6) . . . . ?
C1 N2 C2 C3 -2.5(6) . . . . ?
C1 N2 C2 C22 169.7(7) . . . . ?
C1 N2 C16 C17 -12.7(8) . . . . ?
C1 N2 C16 C21 162.0(6) . . . . ?
C1 C10 C15 C17 -5.5(8) . . . . ?
C1 C10 C15 C14 179.2(6) . . . . ?
C1 C10 C11 C9 -0.9(9) . . . . ?
C1 C10 C11 C12 -178.6(6) . . . . ?
C3 N1 C1 N2 -0.6(7) . . . . ?
C3 N1 C1 C10 178.0(6) . . . . ?
C3 N1 C4 C9 -179.9(6) . . . . ?
C3 N1 C4 C5 -1.2(9) . . . . ?
C3 C2 C22 C27 -7.1(8) . . . . ?
C3 C2 C22 C23 171.1(6) . . . . ?
C3 C28 C33 C5 1.7(9) . . . . ?
C3 C28 C33 C32 179.4(6) . . . . ?
C16 N2 C2 C3 169.2(6) . . . . ?
C16 N2 C2 C22 -18.6(13) . . . . ?
C16 N2 C1 N1 -171.7(5) . . . . ?
C16 N2 C1 C10 9.9(9) . . . . ?
C16 C17 C18 C19 -1.4(10) . . . . ?
C16 C21 C20 C19 2.9(11) . . . . ?
C40 N3 C38 N4 0.3(7) . . . . ?
C40 N3 C38 C47 -176.5(6) . . . . ?
C40 N3 C41 C46 178.4(6) . . . . ?
C40 N3 C41 C42 -0.1(9) . . . . ?
C40 C65 C66 C64 3.2(9) . . . . ?
C40 C65 C66 C67 -178.5(6) . . . . ?
C40 C65 C70 C42 -4.0(9) . . . . ?
C40 C65 C70 C69 178.5(6) . . . . ?
C40 C39 C59 C60 -170.1(6) . . . . ?
C40 C39 C59 C64 5.6(8) . . . . ?
C65 C40 C39 N4 -177.1(6) . . . . ?
C65 C40 C39 C59 -3.3(10) . . . . ?
C65 C66 C64 C59 -0.5(9) . . . . ?
C65 C66 C64 C63 178.1(6) . . . . ?
C65 C66 C67 C68 -0.7(10) . . . . ?
C65 C70 C69 C68 0.7(10) . . . . ?
C10 C15 C17 C16 1.8(9) . . . . ?
C10 C15 C17 C18 -171.4(6) . . . . ?
C10 C15 C14 C13 0.5(10) . . . . ?
C10 C11 C12 C13 -1.7(10) . . . . ?
C15 C10 C11 C9 -179.2(6) . . . . ?
C15 C10 C11 C12 3.1(10) . . . . ?
C15 C17 C18 C19 172.1(7) . . . . ?
C15 C14 C13 C12 0.7(11) . . . . ?
C29 C27 C26 C25 174.4(7) . . . . ?
C29 C28 C33 C5 -177.7(6) . . . . ?
C29 C28 C33 C32 0.0(9) . . . . ?
C29 C30 C31 C32 0.4(10) . . . . ?
C22 C2 C3 N1 -172.2(5) . . . . ?
C22 C2 C3 C28 5.2(10) . . . . ?
C22 C27 C26 C25 -2.5(10) . . . . ?
C22 C23 C24 C25 0.2(11) . . . . ?
C39 N4 C38 N3 -1.0(7) . . . . ?
C39 N4 C38 C47 175.5(6) . . . . ?
C39 N4 C53 C54 -174.0(7) . . . . ?
C39 N4 C53 C58 11.0(11) . . . . ?
C39 C40 C65 C66 -1.4(10) . . . . ?
C39 C40 C65 C70 179.2(6) . . . . ?
C39 C59 C64 C66 -4.1(9) . . . . ?
C39 C59 C64 C63 177.3(6) . . . . ?
C9 C11 C12 C13 -179.3(6) . . . . ?
C38 N3 C40 C65 177.0(6) . . . . ?
C38 N3 C40 C39 0.6(7) . . . . ?
C38 N3 C41 C46 -0.1(9) . . . . ?
C38 N3 C41 C42 -178.6(6) . . . . ?
C38 N4 C39 C40 1.4(6) . . . . ?
C38 N4 C39 C59 -170.2(7) . . . . ?
C38 N4 C53 C54 15.0(8) . . . . ?
C38 N4 C53 C58 -160.0(6) . . . . ?
C17 C16 C21 C20 -7.0(10) . . . . ?
C17 C15 C14 C13 -174.3(6) . . . . ?
C17 C18 C19 C20 -2.6(11) . . . . ?
C41 N3 C40 C65 -1.7(9) . . . . ?
C41 N3 C40 C39 -178.1(5) . . . . ?
C41 N3 C38 N4 178.9(5) . . . . ?
C41 N3 C38 C47 2.2(10) . . . . ?
C41 C46 C45 C44 1.9(10) . . . . ?
C41 C46 C48 C47 0.0(9) . . . . ?
C41 C46 C48 C49 -177.9(7) . . . . ?
C41 C42 C43 C44 -2.4(10) . . . . ?
C41 C42 C70 C65 2.3(10) . . . . ?
C41 C42 C70 C69 179.6(7) . . . . ?
C46 C41 C42 C43 2.8(10) . . . . ?
C46 C41 C42 C70 -178.6(6) . . . . ?
C46 C45 C44 C43 -1.8(10) . . . . ?
C46 C45 C44 C71 179.5(7) . . . . ?
C46 C48 C47 C38 2.0(9) . . . . ?
C46 C48 C47 C52 -177.1(6) . . . . ?
C46 C48 C49 C50 175.8(7) . . . . ?
C53 N4 C39 C40 -170.2(7) . . . . ?
C53 N4 C39 C59 18.2(13) . . . . ?
C53 N4 C38 N3 172.5(5) . . . . ?
C53 N4 C38 C47 -10.9(9) . . . . ?
C53 C54 C55 C56 5.3(12) . . . . ?
C53 C58 C57 C56 -1.2(12) . . . . ?
C5 C33 C32 C31 178.1(6) . . . . ?
C27 C29 C28 C3 -1.6(8) . . . . ?
C27 C29 C28 C33 177.9(6) . . . . ?
C27 C29 C30 C31 -177.9(6) . . . . ?
C27 C22 C23 C24 -2.8(10) . . . . ?
C27 C26 C25 C24 -0.1(11) . . . . ?
C66 C65 C70 C42 176.7(6) . . . . ?
C66 C65 C70 C69 -0.9(10) . . . . ?
C66 C64 C63 C62 -175.7(7) . . . . ?
C66 C67 C68 C69 0.7(12) . . . . ?
C28 C29 C27 C22 -0.8(9) . . . . ?
C28 C29 C27 C26 -177.5(6) . . . . ?
C28 C29 C30 C31 0.2(9) . . . . ?
C28 C33 C32 C31 0.6(9) . . . . ?
C4 N1 C1 N2 177.8(5) . . . . ?
C4 N1 C1 C10 -3.7(9) . . . . ?
C4 N1 C3 C2 -179.4(5) . . . . ?
C4 N1 C3 C28 2.9(9) . . . . ?
C4 C9 C11 C10 -0.6(9) . . . . ?
C4 C9 C11 C12 177.0(6) . . . . ?
C4 C9 C8 C7 0.0(10) . . . . ?
C4 C5 C33 C28 -0.2(9) . . . . ?
C4 C5 C33 C32 -177.6(6) . . . . ?
C4 C5 C6 C7 0.8(9) . . . . ?
C23 C22 C27 C29 -172.9(6) . . . . ?
C23 C22 C27 C26 3.9(9) . . . . ?
C23 C24 C25 C26 1.3(11) . . . . ?
C11 C10 C15 C17 172.7(6) . . . . ?
C11 C10 C15 C14 -2.5(9) . . . . ?
C11 C9 C4 N1 0.1(9) . . . . ?
C11 C9 C4 C5 -178.4(6) . . . . ?
C11 C9 C8 C7 -179.9(6) . . . . ?
C11 C12 C13 C14 -0.1(11) . . . . ?
C42 C41 C46 C45 -2.5(10) . . . . ?
C42 C41 C46 C48 177.4(6) . . . . ?
C42 C43 C44 C45 2.1(10) . . . . ?
C42 C43 C44 C71 -179.1(6) . . . . ?
C42 C70 C69 C68 -176.6(7) . . . . ?
C33 C5 C4 N1 -0.2(8) . . . . ?
C33 C5 C4 C9 178.4(6) . . . . ?
C33 C5 C6 C7 -179.7(6) . . . . ?
C33 C32 C31 C30 -0.8(10) . . . . ?
C60 C59 C64 C66 172.0(6) . . . . ?
C60 C59 C64 C63 -6.7(9) . . . . ?
C60 C61 C62 C63 -2.7(12) . . . . ?
C45 C46 C48 C47 179.9(6) . . . . ?
C45 C46 C48 C49 2.0(11) . . . . ?
C45 C44 C71 C73 -118.7(8) . . . . ?
C45 C44 C71 C74 122.6(8) . . . . ?
C45 C44 C71 C72 0.1(11) . . . . ?
C48 C46 C45 C44 -178.1(6) . . . . ?
C48 C49 C50 C51 1.9(13) . . . . ?
C59 C60 C61 C62 -1.4(12) . . . . ?
C59 C64 C63 C62 3.0(11) . . . . ?
C52 C54 C55 C56 -169.6(8) . . . . ?
C52 C51 C50 C49 -0.3(13) . . . . ?
C43 C42 C70 C65 -179.2(6) . . . . ?
C43 C42 C70 C69 -2.0(12) . . . . ?
C43 C44 C71 C73 62.5(9) . . . . ?
C43 C44 C71 C74 -56.2(9) . . . . ?
C43 C44 C71 C72 -178.7(8) . . . . ?
C64 C66 C67 C68 177.4(7) . . . . ?
C64 C63 C62 C61 1.7(12) . . . . ?
C30 C29 C27 C22 177.2(6) . . . . ?
C30 C29 C27 C26 0.5(10) . . . . ?
C30 C29 C28 C3 -179.9(6) . . . . ?
C30 C29 C28 C33 -0.4(9) . . . . ?
C47 C48 C49 C50 -2.2(11) . . . . ?
C47 C52 C54 C53 -1.0(10) . . . . ?
C47 C52 C54 C55 173.6(7) . . . . ?
C47 C52 C51 C50 -0.9(11) . . . . ?
C6 C5 C4 N1 179.3(5) . . . . ?
C6 C5 C4 C9 -2.1(9) . . . . ?
C6 C5 C33 C28 -179.6(6) . . . . ?
C6 C5 C33 C32 2.9(11) . . . . ?
C6 C7 C8 C9 -1.1(11) . . . . ?
C6 C7 C34 C37 -57.5(11) . . . . ?
C6 C7 C34 C35 -179.7(9) . . . . ?
C6 C7 C34 C36 58.3(10) . . . . ?
C6 C7 C34 C36A 116(2) . . . . ?
C6 C7 C34 C37A -3(3) . . . . ?
C6 C7 C34 C35A -136(3) . . . . ?
C8 C9 C4 N1 -179.7(6) . . . . ?
C8 C9 C4 C5 1.7(10) . . . . ?
C8 C9 C11 C10 179.3(6) . . . . ?
C8 C9 C11 C12 -3.2(11) . . . . ?
C8 C7 C6 C5 0.7(11) . . . . ?
C8 C7 C34 C37 120.4(9) . . . . ?
C8 C7 C34 C35 -1.8(13) . . . . ?
C8 C7 C34 C36 -123.8(9) . . . . ?
C8 C7 C34 C36A -66(2) . . . . ?
C8 C7 C34 C37A 175(3) . . . . ?
C8 C7 C34 C35A 42(3) . . . . ?
C70 C65 C66 C64 -177.4(6) . . . . ?
C70 C65 C66 C67 0.9(10) . . . . ?
C70 C42 C43 C44 179.0(6) . . . . ?
C70 C69 C68 C67 -0.7(12) . . . . ?
C54 C53 C58 C57 7.5(11) . . . . ?
C54 C52 C47 C38 6.0(10) . . . . ?
C54 C52 C47 C48 -174.9(6) . . . . ?
C54 C52 C51 C50 173.9(8) . . . . ?
C54 C55 C56 C57 0.7(14) . . . . ?
C49 C48 C47 C38 -179.9(6) . . . . ?
C49 C48 C47 C52 1.1(10) . . . . ?
C14 C15 C17 C16 176.4(6) . . . . ?
C14 C15 C17 C18 3.2(10) . . . . ?
C58 C53 C54 C52 165.3(7) . . . . ?
C58 C53 C54 C55 -9.4(10) . . . . ?
C58 C57 C56 C55 -2.9(13) . . . . ?
C67 C66 C64 C59 -178.7(7) . . . . ?
C67 C66 C64 C63 -0.1(10) . . . . ?
C21 C16 C17 C15 -167.2(6) . . . . ?
C21 C16 C17 C18 6.1(9) . . . . ?
C21 C20 C19 C18 2.0(11) . . . . ?
C51 C52 C47 C38 -178.5(7) . . . . ?
C51 C52 C47 C48 0.5(11) . . . . ?
C51 C52 C54 C53 -175.8(8) . . . . ?
C51 C52 C54 C55 -1.2(12) . . . . ?
C61 C60 C59 C39 -178.2(7) . . . . ?
C61 C60 C59 C64 6.1(10) . . . . ?
C34 C7 C6 C5 178.6(7) . . . . ?
C34 C7 C8 C9 -179.0(7) . . . . ?
Cl1 C77 C76 Cl2 7(3) . . . . ?
Cl1 C77 C76 C81 175(3) . . . . ?
Cl1 C77 C78 C79 -173.7(17) . . . . ?
Cl2 C76 C81 C80 180(2) . . . . ?
C77 C76 C81 C80 11(4) . . . . ?
C76 C77 C78 C79 22(4) . . . . ?
C76 C81 C80 C79 -9(4) . . . . ?
C81 C80 C79 C78 11(4) . . . . ?
C80 C79 C78 C77 -15(4) . . . . ?
C78 C77 C76 Cl2 170(4) . . . . ?
C78 C77 C76 C81 -22(4) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.167 0.500 0.000 315 80 '1 C6H4Cl2'
2 0.345 1.000 0.500 315 80 '1 C6H4Cl2'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.523
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichlorobenzene and hexane'
