# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_HR030223
_database_code_depnum_ccdc_archive 'CCDC 2352461'
_audit_update_record             
;
2024-05-01 deposited with the CCDC.	2024-07-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C50 H39 Cl2 F4 N3 S2'
_chemical_formula_sum            'C50 H39 Cl2 F4 N3 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         892.86

_chemical_melting_point          ?

_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                   24.971(3)
_cell_length_b                   14.4865(19)
_cell_length_c                   12.3630(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.316(4)
_cell_angle_gamma                90
_cell_volume                     4399.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.4423
_cell_measurement_theta_max      27.4196
_cell_measurement_temperature    146.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848

_exptl_absorpt_coefficient_mu    0.299
_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  0.71
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      146.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon II 14 '
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            10045
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             10045
_reflns_number_gt                6830
_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          0.1106
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1895
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         10045
_refine_ls_number_parameters     556
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+5.7545P] 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         0.393
_refine_diff_density_min         -0.660
_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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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'

_computing_data_collection       
"Bruker APEX3 v2017.3-0'(Bruker AXS Inc., 2017)"
_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-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1365)'
_computing_publication_material  'APEX4 v2022.1-0 (Bruker AXS Inc., 2022)'

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
S S1_1 0.26221(3) 0.15332(6) 0.36623(7) 0.0373(2) Uani d . . . 1 . .
S S2_1 0.21447(3) 0.34440(6) 0.57916(6) 0.03385(19) Uani d . . . 1 . .
F F1_1 0.36593(8) 0.47816(15) 0.48924(15) 0.0429(5) Uani d . . . 1 . .
F F2_1 0.46459(9) 0.58676(18) 0.22653(18) 0.0607(7) Uani d . . . 1 . .
F F3_1 0.18807(9) 0.80902(16) 0.2037(2) 0.0593(6) Uani d . . . 1 . .
F F4_1 0.23909(9) 0.61557(17) 0.50946(17) 0.0537(6) Uani d . . . 1 . .
N N1_1 0.36932(10) 0.32091(18) 0.3455(2) 0.0275(5) Uani d . . . 1 . .
H H1_1 0.3443(15) 0.335(3) 0.377(3) 0.041000 Uiso d U . . 1 . .
N N2_1 0.22690(9) 0.48650(19) 0.1941(2) 0.0303(6) Uani d . . . 1 . .
N N3_1 0.15504(9) 0.50030(18) 0.3939(2) 0.0293(5) Uani d . . . 1 . .
H H3_1 0.187607 0.483784 0.428119 0.035000 Uiso calc U . R 1 . .
C C1_1 0.37969(13) 0.0654(2) 0.3875(3) 0.0336(7) Uani d . . . 1 . .
C C2_1 0.35378(13) 0.0390(2) 0.2838(3) 0.0373(7) Uani d . . . 1 . .
H H2_1 0.335889 0.084500 0.234910 0.045000 Uiso calc U . R 1 . .
C C3_1 0.35320(15) -0.0516(3) 0.2493(3) 0.0455(8) Uani d . . . 1 . .
H H3A_1 0.334497 -0.067903 0.178015 0.055000 Uiso calc U . R 1 . .
C C4_1 0.37987(17) -0.1189(3) 0.3184(4) 0.0566(11) Uani d . . . 1 . .
C C5_1 0.40740(18) -0.0930(3) 0.4210(4) 0.0595(11) Uani d . . . 1 . .
H H5_1 0.426755 -0.138186 0.468266 0.071000 Uiso calc U . R 1 . .
C C6_1 0.40724(15) -0.0027(3) 0.4559(3) 0.0441(8) Uani d . . . 1 . .
H H6_1 0.426042 0.013472 0.527081 0.053000 Uiso calc U . R 1 . .
C C7_1 0.37616(12) 0.1628(2) 0.4297(2) 0.0303(6) Uani d . . . 1 . .
H H7_1 0.403174 0.167933 0.499652 0.036000 Uiso calc U . R 1 . .
C C8_1 0.39143(11) 0.2343(2) 0.3513(2) 0.0278(6) Uani d . . . 1 . .
C C9_1 0.39142(11) 0.3756(2) 0.2749(2) 0.0256(6) Uani d . . . 1 . .
C C10_1 0.42902(11) 0.3223(2) 0.2351(2) 0.0286(6) Uani d . . . 1 . .
H H10_1 0.451291 0.341665 0.184574 0.034000 Uiso calc U . R 1 . .
C C11_1 0.42877(12) 0.2331(2) 0.2828(2) 0.0314(7) Uani d . . . 1 . .
H H11_1 0.450561 0.182057 0.269562 0.038000 Uiso calc U . R 1 . .
C C12_1 0.3795(3) -0.2193(4) 0.2793(6) 0.107(2) Uani d . . . 1 . .
H H12A_1 0.342095 -0.237652 0.248152 0.161000 Uiso calc U . R 1 . .
H H12B_1 0.393620 -0.259446 0.341754 0.161000 Uiso calc U . R 1 . .
H H12C_1 0.402369 -0.225147 0.223105 0.161000 Uiso calc U . R 1 . .
C C13_1 0.32078(12) 0.1865(2) 0.4563(2) 0.0285(6) Uani d . . . 1 . .
C C14_1 0.22315(12) 0.2261(2) 0.4295(2) 0.0298(6) Uani d . . . 1 . .
C C15_1 0.25432(11) 0.2709(2) 0.5175(2) 0.0269(6) Uani d . . . 1 . .
C C16_1 0.31070(11) 0.2479(2) 0.5341(2) 0.0274(6) Uani d . . . 1 . .
H H16_1 0.337558 0.271902 0.591446 0.033000 Uiso calc U . R 1 . .
C C17_1 0.37690(10) 0.4760(2) 0.2610(2) 0.0253(6) Uani d . . . 1 . .
H H17_1 0.387369 0.496039 0.190199 0.030000 Uiso calc U . R 1 . .
C C18_1 0.41210(11) 0.5318(2) 0.3520(2) 0.0267(6) Uani d . . . 1 . .
C C19_1 0.40621(12) 0.5309(2) 0.4605(3) 0.0327(7) Uani d . . . 1 . .
C C20_1 0.43905(13) 0.5787(3) 0.5429(3) 0.0415(8) Uani d . . . 1 . .
H H20_1 0.432887 0.576034 0.616449 0.050000 Uiso calc U . R 1 . .
C C21_1 0.48112(14) 0.6307(3) 0.5165(3) 0.0468(9) Uani d . . . 1 . .
H H21_1 0.504041 0.664973 0.571857 0.056000 Uiso calc U . R 1 . .
C C22_1 0.48983(14) 0.6329(3) 0.4104(3) 0.0480(9) Uani d . . . 1 . .
H H22_1 0.519078 0.667702 0.391536 0.058000 Uiso calc U . R 1 . .
C C23_1 0.45551(13) 0.5839(3) 0.3313(3) 0.0380(7) Uani d . . . 1 . .
C C24_1 0.16703(12) 0.2522(2) 0.4079(3) 0.0333(7) Uani d . . . 1 . .
H H24_1 0.140479 0.227852 0.350225 0.040000 Uiso calc U . R 1 . .
C C25_1 0.15708(11) 0.3167(2) 0.4815(3) 0.0305(6) Uani d . . . 1 . .
C C26_1 0.31661(11) 0.4958(2) 0.2509(2) 0.0245(6) Uani d . . . 1 . .
C C27_1 0.29095(11) 0.5704(2) 0.2958(2) 0.0267(6) Uani d . . . 1 . .
H H27_1 0.308814 0.617262 0.342503 0.032000 Uiso calc U . R 1 . .
C C28_1 0.23597(11) 0.5630(2) 0.2599(2) 0.0251(6) Uani d . . . 1 . .
C C29_1 0.27579(11) 0.4451(2) 0.1888(3) 0.0326(7) Uani d . . . 1 . .
H H29_1 0.280599 0.390598 0.148952 0.039000 Uiso calc U . R 1 . .
C C30_1 0.10527(11) 0.3728(2) 0.4761(3) 0.0324(7) Uani d . . . 1 . .
H H30_1 0.075213 0.333569 0.435823 0.039000 Uiso calc U . R 1 . .
C C31_1 0.10719(11) 0.4573(2) 0.4066(2) 0.0301(6) Uani d . . . 1 . .
C C32_1 0.06600(12) 0.5036(2) 0.3392(3) 0.0395(8) Uani d . . . 1 . .
H H32_1 0.028232 0.490096 0.330188 0.047000 Uiso calc U . R 1 . .
C C33_1 0.08989(12) 0.5749(2) 0.2858(3) 0.0369(7) Uani d . . . 1 . .
H H33_1 0.071002 0.617562 0.234295 0.044000 Uiso calc U . R 1 . .
C C34_1 0.14508(11) 0.5716(2) 0.3214(2) 0.0274(6) Uani d . . . 1 . .
C C35_1 0.18996(11) 0.6249(2) 0.2806(2) 0.0292(6) Uani d . . . 1 . .
H H35_1 0.173189 0.650830 0.207422 0.035000 Uiso calc U . R 1 . .
C C36_1 0.21173(12) 0.7071(2) 0.3518(3) 0.0333(7) Uani d . . . 1 . .
C C37_1 0.21069(13) 0.7961(3) 0.3105(3) 0.0432(8) Uani d . . . 1 . .
C C38_1 0.23128(17) 0.8729(3) 0.3714(5) 0.0608(12) Uani d . . . 1 . .
H H38_1 0.229659 0.932498 0.338826 0.073000 Uiso calc U . R 1 . .
C C39_1 0.25404(18) 0.8603(3) 0.4801(5) 0.0674(14) Uani d . . . 1 . .
H H39_1 0.268497 0.911794 0.523238 0.081000 Uiso calc U . R 1 . .
C C40_1 0.25614(16) 0.7749(3) 0.5266(4) 0.0592(11) Uani d . . . 1 . .
H H40_1 0.271480 0.766475 0.602021 0.071000 Uiso calc U . R 1 . .
C C41_1 0.23558(14) 0.7007(3) 0.4623(3) 0.0429(8) Uani d . . . 1 . .
C C42_1 0.17511(13) 0.4534(3) 0.1323(3) 0.0500(10) Uani d . . . 1 . .
H H42A_1 0.155049 0.505139 0.093175 0.075000 Uiso calc U . R 1 . .
H H42B_1 0.153565 0.426177 0.183118 0.075000 Uiso calc U . R 1 . .
H H42C_1 0.181957 0.406595 0.079168 0.075000 Uiso calc U . R 1 . .
C C43_1 0.09134(11) 0.3899(2) 0.5890(3) 0.0330(7) Uani d . . . 1 . .
C C44_1 0.11072(13) 0.4653(3) 0.6535(3) 0.0416(8) Uani d . . . 1 . .
H H44_1 0.132858 0.509626 0.625864 0.050000 Uiso calc U . R 1 . .
C C45_1 0.09827(14) 0.4771(3) 0.7581(3) 0.0432(8) Uani d . . . 1 . .
H H45_1 0.112625 0.528628 0.801221 0.052000 Uiso calc U . R 1 . .
C C46_1 0.06521(12) 0.4145(3) 0.8002(3) 0.0380(8) Uani d . . . 1 . .
C C47_1 0.04637(12) 0.3385(3) 0.7358(3) 0.0390(8) Uani d . . . 1 . .
H H47_1 0.024100 0.294373 0.763331 0.047000 Uiso calc U . R 1 . .
C C48_1 0.05932(12) 0.3256(2) 0.6320(3) 0.0355(7) Uani d . . . 1 . .
H H48_1 0.046240 0.272664 0.590229 0.043000 Uiso calc U . R 1 . .
C C49_1 0.05008(15) 0.4274(3) 0.9118(3) 0.0515(10) Uani d . . . 1 . .
H H49A_1 0.010758 0.418724 0.906288 0.077000 Uiso calc U . R 1 . .
H H49B_1 0.060093 0.489796 0.938592 0.077000 Uiso calc U . R 1 . .
H H49C_1 0.069527 0.381982 0.963091 0.077000 Uiso calc U . R 1 . .
Cl Cl1_2 0.05150(4) 0.80410(8) 0.12665(10) 0.0640(3) Uani d . . . 1 . .
Cl Cl2_2 0.08091(7) 0.69067(11) -0.04589(16) 0.1014(5) Uani d . . . 1 . .
C C1_2 0.08277(18) 0.7996(3) 0.0108(4) 0.0622(12) Uani d . . . 1 . .
H H1A_2 0.064272 0.843351 -0.045166 0.075000 Uiso calc U . R 1 . .
H H1B_2 0.121165 0.819407 0.031834 0.075000 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1_1 C14_1 . 1.717(3) ?
S1_1 C13_1 . 1.740(3) ?
S2_1 C15_1 . 1.725(3) ?
S2_1 C25_1 . 1.747(3) ?
F1_1 C19_1 . 1.360(4) ?
F2_1 C23_1 . 1.356(4) ?
F3_1 C37_1 . 1.354(5) ?
F4_1 C41_1 . 1.361(5) ?
N1_1 C9_1 . 1.366(4) ?
N1_1 C8_1 . 1.368(4) ?
N2_1 C28_1 . 1.369(4) ?
N2_1 C29_1 . 1.372(4) ?
N2_1 C42_1 . 1.460(4) ?
N3_1 C34_1 . 1.361(4) ?
N3_1 C31_1 . 1.381(4) ?
C1_1 C2_1 . 1.383(5) ?
C1_1 C6_1 . 1.397(4) ?
C1_1 C7_1 . 1.513(5) ?
C2_1 C3_1 . 1.379(5) ?
C3_1 C4_1 . 1.386(6) ?
C4_1 C5_1 . 1.382(6) ?
C4_1 C12_1 . 1.532(7) ?
C5_1 C6_1 . 1.378(6) ?
C7_1 C8_1 . 1.513(4) ?
C7_1 C13_1 . 1.517(4) ?
C8_1 C11_1 . 1.367(4) ?
C9_1 C10_1 . 1.373(4) ?
C9_1 C17_1 . 1.502(4) ?
C10_1 C11_1 . 1.420(4) ?
C13_1 C16_1 . 1.366(4) ?
C14_1 C15_1 . 1.381(4) ?
C14_1 C24_1 . 1.430(4) ?
C15_1 C16_1 . 1.425(4) ?
C17_1 C26_1 . 1.515(4) ?
C17_1 C18_1 . 1.528(4) ?
C18_1 C19_1 . 1.376(4) ?
C18_1 C23_1 . 1.382(4) ?
C19_1 C20_1 . 1.375(4) ?
C20_1 C21_1 . 1.379(5) ?
C21_1 C22_1 . 1.368(5) ?
C22_1 C23_1 . 1.376(5) ?
C24_1 C25_1 . 1.359(5) ?
C25_1 C30_1 . 1.519(4) ?
C26_1 C29_1 . 1.373(4) ?
C26_1 C27_1 . 1.419(4) ?
C27_1 C28_1 . 1.369(4) ?
C28_1 C35_1 . 1.515(4) ?
C30_1 C31_1 . 1.502(4) ?
C30_1 C43_1 . 1.517(4) ?
C31_1 C32_1 . 1.377(4) ?
C32_1 C33_1 . 1.414(5) ?
C33_1 C34_1 . 1.371(4) ?
C34_1 C35_1 . 1.519(4) ?
C35_1 C36_1 . 1.522(4) ?
C36_1 C37_1 . 1.386(5) ?
C36_1 C41_1 . 1.392(5) ?
C37_1 C38_1 . 1.390(6) ?
C38_1 C39_1 . 1.374(7) ?
C39_1 C40_1 . 1.362(7) ?
C40_1 C41_1 . 1.379(5) ?
C43_1 C44_1 . 1.387(5) ?
C43_1 C48_1 . 1.393(4) ?
C44_1 C45_1 . 1.394(5) ?
C45_1 C46_1 . 1.388(5) ?
C46_1 C47_1 . 1.390(5) ?
C46_1 C49_1 . 1.506(5) ?
C47_1 C48_1 . 1.390(5) ?
Cl1_2 C1_2 . 1.751(4) ?
Cl2_2 C1_2 . 1.723(5) ?

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
C14_1 S1_1 C13_1 . . 91.12(14) ?
C15_1 S2_1 C25_1 . . 91.15(14) ?
C9_1 N1_1 C8_1 . . 111.1(2) ?
C28_1 N2_1 C29_1 . . 109.1(2) ?
C28_1 N2_1 C42_1 . . 127.8(3) ?
C29_1 N2_1 C42_1 . . 122.9(3) ?
C34_1 N3_1 C31_1 . . 110.9(2) ?
C2_1 C1_1 C6_1 . . 117.6(3) ?
C2_1 C1_1 C7_1 . . 122.1(3) ?
C6_1 C1_1 C7_1 . . 120.2(3) ?
C3_1 C2_1 C1_1 . . 121.8(3) ?
C2_1 C3_1 C4_1 . . 120.1(4) ?
C5_1 C4_1 C3_1 . . 118.7(4) ?
C5_1 C4_1 C12_1 . . 121.4(4) ?
C3_1 C4_1 C12_1 . . 119.9(5) ?
C6_1 C5_1 C4_1 . . 121.1(4) ?
C5_1 C6_1 C1_1 . . 120.6(4) ?
C8_1 C7_1 C1_1 . . 112.4(2) ?
C8_1 C7_1 C13_1 . . 109.2(2) ?
C1_1 C7_1 C13_1 . . 113.4(3) ?
C11_1 C8_1 N1_1 . . 107.0(3) ?
C11_1 C8_1 C7_1 . . 131.8(3) ?
N1_1 C8_1 C7_1 . . 121.0(3) ?
N1_1 C9_1 C10_1 . . 106.5(3) ?
N1_1 C9_1 C17_1 . . 121.2(2) ?
C10_1 C9_1 C17_1 . . 132.1(3) ?
C9_1 C10_1 C11_1 . . 107.9(3) ?
C8_1 C11_1 C10_1 . . 107.5(3) ?
C16_1 C13_1 C7_1 . . 126.2(3) ?
C16_1 C13_1 S1_1 . . 113.0(2) ?
C7_1 C13_1 S1_1 . . 119.5(2) ?
C15_1 C14_1 C24_1 . . 114.7(3) ?
C15_1 C14_1 S1_1 . . 111.2(2) ?
C24_1 C14_1 S1_1 . . 134.0(2) ?
C14_1 C15_1 C16_1 . . 114.0(3) ?
C14_1 C15_1 S2_1 . . 110.5(2) ?
C16_1 C15_1 S2_1 . . 135.5(2) ?
C13_1 C16_1 C15_1 . . 110.6(3) ?
C9_1 C17_1 C26_1 . . 114.1(2) ?
C9_1 C17_1 C18_1 . . 109.4(2) ?
C26_1 C17_1 C18_1 . . 113.1(2) ?
C19_1 C18_1 C23_1 . . 114.2(3) ?
C19_1 C18_1 C17_1 . . 124.4(3) ?
C23_1 C18_1 C17_1 . . 121.3(3) ?
F1_1 C19_1 C20_1 . . 117.5(3) ?
F1_1 C19_1 C18_1 . . 118.2(3) ?
C20_1 C19_1 C18_1 . . 124.3(3) ?
C19_1 C20_1 C21_1 . . 118.6(3) ?
C22_1 C21_1 C20_1 . . 119.9(3) ?
C21_1 C22_1 C23_1 . . 118.9(3) ?
F2_1 C23_1 C22_1 . . 118.2(3) ?
F2_1 C23_1 C18_1 . . 117.7(3) ?
C22_1 C23_1 C18_1 . . 124.1(3) ?
C25_1 C24_1 C14_1 . . 110.3(3) ?
C24_1 C25_1 C30_1 . . 126.5(3) ?
C24_1 C25_1 S2_1 . . 113.3(2) ?
C30_1 C25_1 S2_1 . . 119.7(2) ?
C29_1 C26_1 C27_1 . . 106.5(2) ?
C29_1 C26_1 C17_1 . . 124.9(3) ?
C27_1 C26_1 C17_1 . . 128.5(2) ?
C28_1 C27_1 C26_1 . . 108.1(3) ?
C27_1 C28_1 N2_1 . . 107.7(2) ?
C27_1 C28_1 C35_1 . . 130.3(3) ?
N2_1 C28_1 C35_1 . . 122.0(2) ?
N2_1 C29_1 C26_1 . . 108.5(3) ?
C31_1 C30_1 C43_1 . . 115.4(3) ?
C31_1 C30_1 C25_1 . . 110.3(2) ?
C43_1 C30_1 C25_1 . . 112.4(2) ?
C32_1 C31_1 N3_1 . . 106.2(3) ?
C32_1 C31_1 C30_1 . . 130.3(3) ?
N3_1 C31_1 C30_1 . . 123.3(2) ?
C31_1 C32_1 C33_1 . . 107.8(3) ?
C34_1 C33_1 C32_1 . . 108.0(3) ?
N3_1 C34_1 C33_1 . . 107.0(3) ?
N3_1 C34_1 C35_1 . . 123.1(2) ?
C33_1 C34_1 C35_1 . . 129.4(3) ?
C28_1 C35_1 C34_1 . . 112.5(2) ?
C28_1 C35_1 C36_1 . . 111.0(2) ?
C34_1 C35_1 C36_1 . . 114.4(3) ?
C37_1 C36_1 C41_1 . . 113.5(3) ?
C37_1 C36_1 C35_1 . . 122.3(3) ?
C41_1 C36_1 C35_1 . . 124.2(3) ?
F3_1 C37_1 C36_1 . . 117.7(3) ?
F3_1 C37_1 C38_1 . . 117.9(4) ?
C36_1 C37_1 C38_1 . . 124.4(4) ?
C39_1 C38_1 C37_1 . . 118.1(4) ?
C40_1 C39_1 C38_1 . . 120.8(4) ?
C39_1 C40_1 C41_1 . . 118.8(4) ?
F4_1 C41_1 C40_1 . . 118.0(4) ?
F4_1 C41_1 C36_1 . . 117.6(3) ?
C40_1 C41_1 C36_1 . . 124.4(4) ?
C44_1 C43_1 C48_1 . . 118.1(3) ?
C44_1 C43_1 C30_1 . . 122.9(3) ?
C48_1 C43_1 C30_1 . . 118.9(3) ?
C43_1 C44_1 C45_1 . . 121.1(3) ?
C46_1 C45_1 C44_1 . . 121.0(3) ?
C45_1 C46_1 C47_1 . . 117.7(3) ?
C45_1 C46_1 C49_1 . . 121.8(3) ?
C47_1 C46_1 C49_1 . . 120.5(3) ?
C46_1 C47_1 C48_1 . . 121.6(3) ?
C47_1 C48_1 C43_1 . . 120.5(3) ?
Cl2_2 C1_2 Cl1_2 . . 112.5(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6_1 C1_1 C2_1 C3_1 . . . . 2.2(5) ?
C7_1 C1_1 C2_1 C3_1 . . . . -174.3(3) ?
C1_1 C2_1 C3_1 C4_1 . . . . -1.2(5) ?
C2_1 C3_1 C4_1 C5_1 . . . . -0.9(6) ?
C2_1 C3_1 C4_1 C12_1 . . . . -179.5(4) ?
C3_1 C4_1 C5_1 C6_1 . . . . 1.9(7) ?
C12_1 C4_1 C5_1 C6_1 . . . . -179.5(5) ?
C4_1 C5_1 C6_1 C1_1 . . . . -0.8(6) ?
C2_1 C1_1 C6_1 C5_1 . . . . -1.2(5) ?
C7_1 C1_1 C6_1 C5_1 . . . . 175.3(3) ?
C2_1 C1_1 C7_1 C8_1 . . . . -52.5(4) ?
C6_1 C1_1 C7_1 C8_1 . . . . 131.1(3) ?
C2_1 C1_1 C7_1 C13_1 . . . . 71.9(4) ?
C6_1 C1_1 C7_1 C13_1 . . . . -104.4(3) ?
C9_1 N1_1 C8_1 C11_1 . . . . 0.1(3) ?
C9_1 N1_1 C8_1 C7_1 . . . . 176.0(3) ?
C1_1 C7_1 C8_1 C11_1 . . . . -34.7(4) ?
C13_1 C7_1 C8_1 C11_1 . . . . -161.5(3) ?
C1_1 C7_1 C8_1 N1_1 . . . . 150.5(3) ?
C13_1 C7_1 C8_1 N1_1 . . . . 23.8(4) ?
C8_1 N1_1 C9_1 C10_1 . . . . -0.5(3) ?
C8_1 N1_1 C9_1 C17_1 . . . . -175.3(2) ?
N1_1 C9_1 C10_1 C11_1 . . . . 0.6(3) ?
C17_1 C9_1 C10_1 C11_1 . . . . 174.6(3) ?
N1_1 C8_1 C11_1 C10_1 . . . . 0.3(3) ?
C7_1 C8_1 C11_1 C10_1 . . . . -175.1(3) ?
C9_1 C10_1 C11_1 C8_1 . . . . -0.5(3) ?
C8_1 C7_1 C13_1 C16_1 . . . . -83.4(4) ?
C1_1 C7_1 C13_1 C16_1 . . . . 150.5(3) ?
C8_1 C7_1 C13_1 S1_1 . . . . 82.8(3) ?
C1_1 C7_1 C13_1 S1_1 . . . . -43.3(3) ?
C14_1 S1_1 C13_1 C16_1 . . . . 2.3(2) ?
C14_1 S1_1 C13_1 C7_1 . . . . -165.6(3) ?
C13_1 S1_1 C14_1 C15_1 . . . . -1.8(2) ?
C13_1 S1_1 C14_1 C24_1 . . . . 175.2(3) ?
C24_1 C14_1 C15_1 C16_1 . . . . -176.7(3) ?
S1_1 C14_1 C15_1 C16_1 . . . . 0.9(3) ?
C24_1 C14_1 C15_1 S2_1 . . . . 1.9(3) ?
S1_1 C14_1 C15_1 S2_1 . . . . 179.47(16) ?
C25_1 S2_1 C15_1 C14_1 . . . . -2.3(2) ?
C25_1 S2_1 C15_1 C16_1 . . . . 175.9(3) ?
C7_1 C13_1 C16_1 C15_1 . . . . 164.7(3) ?
S1_1 C13_1 C16_1 C15_1 . . . . -2.2(3) ?
C14_1 C15_1 C16_1 C13_1 . . . . 0.8(4) ?
S2_1 C15_1 C16_1 C13_1 . . . . -177.3(3) ?
N1_1 C9_1 C17_1 C26_1 . . . . -44.4(4) ?
C10_1 C9_1 C17_1 C26_1 . . . . 142.3(3) ?
N1_1 C9_1 C17_1 C18_1 . . . . 83.5(3) ?
C10_1 C9_1 C17_1 C18_1 . . . . -89.8(4) ?
C9_1 C17_1 C18_1 C19_1 . . . . -71.8(4) ?
C26_1 C17_1 C18_1 C19_1 . . . . 56.5(4) ?
C9_1 C17_1 C18_1 C23_1 . . . . 104.1(3) ?
C26_1 C17_1 C18_1 C23_1 . . . . -127.5(3) ?
C23_1 C18_1 C19_1 F1_1 . . . . -177.3(3) ?
C17_1 C18_1 C19_1 F1_1 . . . . -1.0(5) ?
C23_1 C18_1 C19_1 C20_1 . . . . 1.6(5) ?
C17_1 C18_1 C19_1 C20_1 . . . . 177.8(3) ?
F1_1 C19_1 C20_1 C21_1 . . . . 178.3(3) ?
C18_1 C19_1 C20_1 C21_1 . . . . -0.6(5) ?
C19_1 C20_1 C21_1 C22_1 . . . . -0.8(6) ?
C20_1 C21_1 C22_1 C23_1 . . . . 1.0(6) ?
C21_1 C22_1 C23_1 F2_1 . . . . 179.9(4) ?
C21_1 C22_1 C23_1 C18_1 . . . . 0.1(6) ?
C19_1 C18_1 C23_1 F2_1 . . . . 178.8(3) ?
C17_1 C18_1 C23_1 F2_1 . . . . 2.5(5) ?
C19_1 C18_1 C23_1 C22_1 . . . . -1.3(5) ?
C17_1 C18_1 C23_1 C22_1 . . . . -177.7(3) ?
C15_1 C14_1 C24_1 C25_1 . . . . -0.2(4) ?
S1_1 C14_1 C24_1 C25_1 . . . . -177.1(3) ?
C14_1 C24_1 C25_1 C30_1 . . . . 169.8(3) ?
C14_1 C24_1 C25_1 S2_1 . . . . -1.5(3) ?
C15_1 S2_1 C25_1 C24_1 . . . . 2.2(3) ?
C15_1 S2_1 C25_1 C30_1 . . . . -169.7(2) ?
C9_1 C17_1 C26_1 C29_1 . . . . -43.1(4) ?
C18_1 C17_1 C26_1 C29_1 . . . . -169.0(3) ?
C9_1 C17_1 C26_1 C27_1 . . . . 141.1(3) ?
C18_1 C17_1 C26_1 C27_1 . . . . 15.2(4) ?
C29_1 C26_1 C27_1 C28_1 . . . . -0.1(3) ?
C17_1 C26_1 C27_1 C28_1 . . . . 176.4(3) ?
C26_1 C27_1 C28_1 N2_1 . . . . -0.2(3) ?
C26_1 C27_1 C28_1 C35_1 . . . . -178.5(3) ?
C29_1 N2_1 C28_1 C27_1 . . . . 0.5(3) ?
C42_1 N2_1 C28_1 C27_1 . . . . -176.4(3) ?
C29_1 N2_1 C28_1 C35_1 . . . . 178.9(3) ?
C42_1 N2_1 C28_1 C35_1 . . . . 2.1(5) ?
C28_1 N2_1 C29_1 C26_1 . . . . -0.5(4) ?
C42_1 N2_1 C29_1 C26_1 . . . . 176.5(3) ?
C27_1 C26_1 C29_1 N2_1 . . . . 0.3(4) ?
C17_1 C26_1 C29_1 N2_1 . . . . -176.2(3) ?
C24_1 C25_1 C30_1 C31_1 . . . . -85.7(4) ?
S2_1 C25_1 C30_1 C31_1 . . . . 85.1(3) ?
C24_1 C25_1 C30_1 C43_1 . . . . 144.0(3) ?
S2_1 C25_1 C30_1 C43_1 . . . . -45.2(3) ?
C34_1 N3_1 C31_1 C32_1 . . . . 0.1(4) ?
C34_1 N3_1 C31_1 C30_1 . . . . 176.2(3) ?
C43_1 C30_1 C31_1 C32_1 . . . . -84.2(4) ?
C25_1 C30_1 C31_1 C32_1 . . . . 147.2(4) ?
C43_1 C30_1 C31_1 N3_1 . . . . 100.7(3) ?
C25_1 C30_1 C31_1 N3_1 . . . . -27.9(4) ?
N3_1 C31_1 C32_1 C33_1 . . . . 0.1(4) ?
C30_1 C31_1 C32_1 C33_1 . . . . -175.6(3) ?
C31_1 C32_1 C33_1 C34_1 . . . . -0.3(4) ?
C31_1 N3_1 C34_1 C33_1 . . . . -0.3(4) ?
C31_1 N3_1 C34_1 C35_1 . . . . -172.7(3) ?
C32_1 C33_1 C34_1 N3_1 . . . . 0.4(4) ?
C32_1 C33_1 C34_1 C35_1 . . . . 172.1(3) ?
C27_1 C28_1 C35_1 C34_1 . . . . -128.7(3) ?
N2_1 C28_1 C35_1 C34_1 . . . . 53.2(4) ?
C27_1 C28_1 C35_1 C36_1 . . . . 0.9(4) ?
N2_1 C28_1 C35_1 C36_1 . . . . -177.2(3) ?
N3_1 C34_1 C35_1 C28_1 . . . . 39.1(4) ?
C33_1 C34_1 C35_1 C28_1 . . . . -131.5(3) ?
N3_1 C34_1 C35_1 C36_1 . . . . -88.8(3) ?
C33_1 C34_1 C35_1 C36_1 . . . . 100.7(4) ?
C28_1 C35_1 C36_1 C37_1 . . . . 109.4(3) ?
C34_1 C35_1 C36_1 C37_1 . . . . -122.0(3) ?
C28_1 C35_1 C36_1 C41_1 . . . . -68.9(4) ?
C34_1 C35_1 C36_1 C41_1 . . . . 59.7(4) ?
C41_1 C36_1 C37_1 F3_1 . . . . -179.8(3) ?
C35_1 C36_1 C37_1 F3_1 . . . . 1.7(5) ?
C41_1 C36_1 C37_1 C38_1 . . . . 0.2(5) ?
C35_1 C36_1 C37_1 C38_1 . . . . -178.3(3) ?
F3_1 C37_1 C38_1 C39_1 . . . . 179.7(3) ?
C36_1 C37_1 C38_1 C39_1 . . . . -0.3(6) ?
C37_1 C38_1 C39_1 C40_1 . . . . -0.2(6) ?
C38_1 C39_1 C40_1 C41_1 . . . . 0.8(6) ?
C39_1 C40_1 C41_1 F4_1 . . . . 178.6(3) ?
C39_1 C40_1 C41_1 C36_1 . . . . -1.0(6) ?
C37_1 C36_1 C41_1 F4_1 . . . . -179.1(3) ?
C35_1 C36_1 C41_1 F4_1 . . . . -0.6(5) ?
C37_1 C36_1 C41_1 C40_1 . . . . 0.5(5) ?
C35_1 C36_1 C41_1 C40_1 . . . . 178.9(3) ?
C31_1 C30_1 C43_1 C44_1 . . . . -39.0(4) ?
C25_1 C30_1 C43_1 C44_1 . . . . 88.6(4) ?
C31_1 C30_1 C43_1 C48_1 . . . . 143.5(3) ?
C25_1 C30_1 C43_1 C48_1 . . . . -88.9(3) ?
C48_1 C43_1 C44_1 C45_1 . . . . -0.5(5) ?
C30_1 C43_1 C44_1 C45_1 . . . . -178.1(3) ?
C43_1 C44_1 C45_1 C46_1 . . . . -1.2(5) ?
C44_1 C45_1 C46_1 C47_1 . . . . 1.9(5) ?
C44_1 C45_1 C46_1 C49_1 . . . . -178.3(3) ?
C45_1 C46_1 C47_1 C48_1 . . . . -0.9(5) ?
C49_1 C46_1 C47_1 C48_1 . . . . 179.3(3) ?
C46_1 C47_1 C48_1 C43_1 . . . . -0.8(5) ?
C44_1 C43_1 C48_1 C47_1 . . . . 1.5(4) ?
C30_1 C43_1 C48_1 C47_1 . . . . 179.2(3) ?



