#------------------------------------------------------------------------------
#$Date: 2021-12-07 04:54:30 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243770
loop_
_publ_author_name
'Okayasu, Misaki'
'Kikkawa, Shoko'
'Hikawa, Hidemasa'
'Azumaya, Isao'
_publ_section_title
;
 Relationship between crystal shape and unit cell shape: crystal shape
 modification via co-crystallization toward SXRD-suitable crystals
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              7760
_journal_page_last               7770
_journal_paper_doi               10.1039/D1CE00897H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C54 H42 Br4 N8 O4 S2'
_chemical_formula_sum            'C54 H42 Br4 N8 O4 S2'
_chemical_formula_weight         1250.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                99.089(2)
_cell_angle_beta                 98.944(2)
_cell_angle_gamma                110.799(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7276(4)
_cell_length_b                   14.3853(4)
_cell_length_c                   16.9385(5)
_cell_measurement_reflns_used    19669
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.65
_cell_volume                     2567.63(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            81776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.502
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1252.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     657
_refine_ls_number_reflns         11753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0223P)²+1.5215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8532
_reflns_number_total             11753
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1ce00897h2.cif
_cod_data_source_block           mfu355-s22a21N-block
_cod_depositor_comments
'Adding full bibliography for 7243759--7243776.cif.'
_cod_database_code               7243770
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.19338(3) 0.86506(2) 0.32336(2) 0.02346(8) Uani 1 1 d . . . . .
Br2 Br 0.58281(3) 1.00858(2) 0.27441(2) 0.03275(9) Uani 1 1 d . . . . .
Br3 Br -0.15490(3) 0.59964(2) 1.15621(2) 0.02460(8) Uani 1 1 d . . . . .
Br4 Br 0.47138(3) 0.47383(2) 1.15727(2) 0.03367(9) Uani 1 1 d . . . . .
S1 S 0.70413(6) 0.64355(5) 0.38456(4) 0.01655(15) Uani 1 1 d . . . . .
S2 S 0.31838(6) 0.84525(5) 1.09369(4) 0.01818(15) Uani 1 1 d . . . . .
O1 O 0.60447(17) 0.57993(14) 0.41508(11) 0.0221(4) Uani 1 1 d . . . . .
O2 O 0.75108(17) 0.59760(14) 0.32242(11) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.41491(17) 0.91684(14) 1.06630(11) 0.0226(4) Uani 1 1 d . . . . .
O4 O 0.27092(17) 0.88047(14) 1.16045(11) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.8186(2) 0.70456(18) 0.46533(15) 0.0168(5) Uani 1 1 d . . . . .
N2 N 0.2028(2) 0.79071(17) 1.01252(15) 0.0175(5) Uani 1 1 d . . . . .
N3 N 0.7047(2) 0.74239(18) 0.59693(14) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.3158(2) 0.76517(17) 0.87537(14) 0.0203(5) Uani 1 1 d . . . . .
N5 N 1.0818(2) 0.9543(2) 0.74765(15) 0.0313(6) Uani 1 1 d . . . . .
N6 N 0.7192(2) 0.8489(2) 1.04828(17) 0.0356(7) Uani 1 1 d . . . . .
N7 N 0.6379(2) 0.2860(2) 0.50082(16) 0.0317(6) Uani 1 1 d . . . . .
N8 N 1.1292(2) 0.4874(2) 0.29605(16) 0.0314(6) Uani 1 1 d . . . . .
C1 C 0.9335(2) 0.78502(19) 0.46650(15) 0.0146(6) Uani 1 1 d . . . . .
C2 C 0.9942(2) 0.7852(2) 0.40179(16) 0.0164(6) Uani 1 1 d . . . . .
H2A H 0.957898 0.732650 0.352931 0.020 Uiso 1 1 calc R U . . .
C3 C 1.1093(2) 0.8645(2) 0.41083(16) 0.0170(6) Uani 1 1 d . . . . .
C4 C 1.1652(3) 0.9425(2) 0.48079(16) 0.0198(6) Uani 1 1 d . . . . .
H4 H 1.243815 0.995808 0.485201 0.024 Uiso 1 1 calc R U . . .
C5 C 1.1030(3) 0.9409(2) 0.54487(17) 0.0203(6) Uani 1 1 d . . . . .
H5 H 1.139591 0.993547 0.593670 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9888(2) 0.8630(2) 0.53753(16) 0.0171(6) Uani 1 1 d . . . . .
H6 H 0.947321 0.862610 0.581463 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6599(2) 0.7369(2) 0.34864(16) 0.0167(6) Uani 1 1 d . . . . .
C8 C 0.5901(2) 0.7788(2) 0.39120(17) 0.0196(6) Uani 1 1 d . . . . .
H8 H 0.560857 0.753152 0.435782 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5644(3) 0.8580(2) 0.36744(17) 0.0221(6) Uani 1 1 d . . . . .
H9 H 0.516687 0.887420 0.395356 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6088(3) 0.8943(2) 0.30242(17) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.6724(3) 0.8501(2) 0.25728(17) 0.0212(6) Uani 1 1 d . . . . .
H11 H 0.697280 0.873459 0.210836 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6992(2) 0.7709(2) 0.28112(16) 0.0189(6) Uani 1 1 d . . . . .
H12 H 0.744071 0.739929 0.251601 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0898(2) 0.7076(2) 1.00929(16) 0.0155(6) Uani 1 1 d . . . . .
C14 C 0.0313(3) 0.6371(2) 0.93407(17) 0.0196(6) Uani 1 1 d . . . . .
H14 H 0.069479 0.644543 0.888655 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0809(3) 0.5569(2) 0.92507(17) 0.0227(7) Uani 1 1 d . . . . .
H15 H -0.120330 0.510164 0.873250 0.027 Uiso 1 1 calc R U . . .
C16 C -0.1370(3) 0.5436(2) 0.99112(17) 0.0229(7) Uani 1 1 d . . . . .
H16 H -0.213530 0.487378 0.985717 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0782(2) 0.6147(2) 1.06509(16) 0.0179(6) Uani 1 1 d . . . . .
C18 C 0.0336(2) 0.6969(2) 1.07555(16) 0.0175(6) Uani 1 1 d . . . . .
H18 H 0.071155 0.745028 1.126853 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3682(2) 0.7486(2) 1.11717(16) 0.0184(6) Uani 1 1 d . . . . .
C20 C 0.3329(3) 0.7018(2) 1.18054(16) 0.0210(6) Uani 1 1 d . . . . .
H20 H 0.286406 0.725108 1.214325 0.025 Uiso 1 1 calc R U . . .
C21 C 0.3657(3) 0.6214(2) 1.19401(17) 0.0227(7) Uani 1 1 d . . . . .
H21 H 0.342793 0.589269 1.237258 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4326(3) 0.5884(2) 1.14334(18) 0.0226(6) Uani 1 1 d . . . . .
C23 C 0.4713(3) 0.6363(2) 1.08179(18) 0.0237(7) Uani 1 1 d . . . . .
H23 H 0.519658 0.613943 1.049125 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4389(3) 0.7165(2) 1.06847(17) 0.0219(6) Uani 1 1 d . . . . .
H24 H 0.464559 0.749772 1.026319 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7093(3) 0.8315(2) 0.63789(17) 0.0232(7) Uani 1 1 d . . . . .
H25 H 0.765329 0.892629 0.628052 0.028 Uiso 1 1 calc R U . . .
C26 C 0.6370(3) 0.8398(2) 0.69386(17) 0.0197(6) Uani 1 1 d . . . . .
H26 H 0.643414 0.905064 0.721107 0.024 Uiso 1 1 calc R U . . .
C27 C 0.5550(2) 0.7514(2) 0.70968(16) 0.0159(6) Uani 1 1 d . . . . .
C28 C 0.5499(3) 0.6586(2) 0.66701(16) 0.0191(6) Uani 1 1 d . . . . .
H28 H 0.495394 0.596198 0.675857 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6246(3) 0.6580(2) 0.61170(17) 0.0212(6) Uani 1 1 d . . . . .
H29 H 0.618604 0.593749 0.582468 0.025 Uiso 1 1 calc R U . . .
C30 C 0.4229(3) 0.8441(2) 0.88079(17) 0.0207(6) Uani 1 1 d . . . . .
H30 H 0.444684 0.904536 0.921976 0.025 Uiso 1 1 calc R U . . .
C31 C 0.5034(2) 0.8422(2) 0.82944(16) 0.0177(6) Uani 1 1 d . . . . .
H31 H 0.578691 0.899986 0.836099 0.021 Uiso 1 1 calc R U . . .
C32 C 0.4736(2) 0.75529(19) 0.76810(15) 0.0135(6) Uani 1 1 d . . . . .
C33 C 0.3632(2) 0.6726(2) 0.76349(16) 0.0173(6) Uani 1 1 d . . . . .
H33 H 0.339828 0.610781 0.723593 0.021 Uiso 1 1 calc R U . . .
C34 C 0.2881(3) 0.6808(2) 0.81691(16) 0.0197(6) Uani 1 1 d . . . . .
H34 H 0.212789 0.623785 0.812115 0.024 Uiso 1 1 calc R U . . .
C35 C 1.0761(3) 0.8804(2) 0.78618(19) 0.0336(8) Uani 1 1 d . . . . .
H35 H 1.124350 0.841457 0.773873 0.040 Uiso 1 1 calc R U . . .
C36 C 1.0047(3) 0.8560(2) 0.84321(19) 0.0304(7) Uani 1 1 d . . . . .
H36 H 1.004167 0.801188 0.868188 0.037 Uiso 1 1 calc R U . . .
C37 C 0.9336(3) 0.9114(2) 0.86406(16) 0.0202(6) Uani 1 1 d . . . . .
C38 C 0.9391(3) 0.9898(2) 0.82391(18) 0.0282(7) Uani 1 1 d . . . . .
H38 H 0.892350 1.030437 0.835075 0.034 Uiso 1 1 calc R U . . .
C39 C 1.0134(3) 1.0078(3) 0.76770(19) 0.0342(8) Uani 1 1 d . . . . .
H39 H 1.016158 1.061905 0.741403 0.041 Uiso 1 1 calc R U . . .
C40 C 0.7566(3) 0.7805(3) 1.0094(2) 0.0458(10) Uani 1 1 d . . . . .
H40 H 0.735715 0.716600 1.024436 0.055 Uiso 1 1 calc R U . . .
C41 C 0.8232(3) 0.7956(3) 0.9491(2) 0.0367(8) Uani 1 1 d . . . . .
H41 H 0.845258 0.742938 0.923212 0.044 Uiso 1 1 calc R U . . .
C42 C 0.8577(3) 0.8891(2) 0.92659(17) 0.0217(6) Uani 1 1 d . . . . .
C43 C 0.8190(3) 0.9603(2) 0.96634(17) 0.0261(7) Uani 1 1 d . . . . .
H43 H 0.839465 1.025276 0.953284 0.031 Uiso 1 1 calc R U . . .
C44 C 0.7501(3) 0.9367(3) 1.02532(19) 0.0310(7) Uani 1 1 d . . . . .
H44 H 0.723475 0.986599 1.050752 0.037 Uiso 1 1 calc R U . . .
C45 C 0.6901(3) 0.3861(2) 0.50287(18) 0.0308(7) Uani 1 1 d . . . . .
H45 H 0.658017 0.430057 0.531350 0.037 Uiso 1 1 calc R U . . .
C46 C 0.7874(3) 0.4296(2) 0.46630(17) 0.0258(7) Uani 1 1 d . . . . .
H46 H 0.820463 0.501205 0.470201 0.031 Uiso 1 1 calc R U . . .
C47 C 0.8365(3) 0.3677(2) 0.42381(17) 0.0216(6) Uani 1 1 d . . . . .
C48 C 0.7828(3) 0.2635(2) 0.42141(18) 0.0267(7) Uani 1 1 d . . . . .
H48 H 0.812853 0.217582 0.393470 0.032 Uiso 1 1 calc R U . . .
C49 C 0.6859(3) 0.2275(3) 0.45984(19) 0.0331(8) Uani 1 1 d . . . . .
H49 H 0.650915 0.156195 0.456934 0.040 Uiso 1 1 calc R U . . .
C50 C 1.0606(3) 0.5390(2) 0.3197(2) 0.0326(8) Uani 1 1 d . . . . .
H50 H 1.077751 0.604131 0.307483 0.039 Uiso 1 1 calc R U . . .
C51 C 0.9667(3) 0.5038(2) 0.36059(19) 0.0286(7) Uani 1 1 d . . . . .
H51 H 0.920501 0.543963 0.374639 0.034 Uiso 1 1 calc R U . . .
C52 C 0.9395(3) 0.4100(2) 0.38126(17) 0.0225(6) Uani 1 1 d . . . . .
C53 C 1.0119(3) 0.3558(2) 0.35789(18) 0.0250(7) Uani 1 1 d . . . . .
H53 H 0.998486 0.291332 0.370718 0.030 Uiso 1 1 calc R U . . .
C54 C 1.1032(3) 0.3969(2) 0.31595(18) 0.0303(7) Uani 1 1 d . . . . .
H54 H 1.150333 0.358221 0.300300 0.036 Uiso 1 1 calc R U . . .
H1 H 0.791(3) 0.714(2) 0.5012(18) 0.013(8) Uiso 1 1 d . . . . .
H2 H 0.233(3) 0.783(2) 0.974(2) 0.033(10) Uiso 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
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
O1 S1 O2 119.46(11) . . ?
O1 S1 N1 104.85(12) . . ?
O2 S1 N1 108.55(12) . . ?
O1 S1 C7 108.89(12) . . ?
O2 S1 C7 108.19(12) . . ?
N1 S1 C7 106.14(12) . . ?
O3 S2 O4 119.77(11) . . ?
O3 S2 N2 104.48(12) . . ?
O4 S2 N2 108.37(12) . . ?
O3 S2 C19 108.60(12) . . ?
O4 S2 C19 108.69(12) . . ?
N2 S2 C19 106.10(12) . . ?
C1 N1 S1 125.12(19) . . ?
C1 N1 H1 114(2) . . ?
S1 N1 H1 108(2) . . ?
C13 N2 S2 124.17(19) . . ?
C13 N2 H2 114(2) . . ?
S2 N2 H2 107(2) . . ?
C29 N3 C25 116.7(2) . . ?
C30 N4 C34 116.9(2) . . ?
C35 N5 C39 115.6(3) . . ?
C44 N6 C40 115.6(3) . . ?
C49 N7 C45 115.5(3) . . ?
C50 N8 C54 115.6(3) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 N1 117.4(2) . . ?
C2 C1 N1 122.7(2) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 Br1 118.7(2) . . ?
C2 C3 Br1 118.55(19) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C12 C7 C8 121.2(3) . . ?
C12 C7 S1 120.0(2) . . ?
C8 C7 S1 118.7(2) . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 Br2 118.5(2) . . ?
C9 C10 Br2 119.4(2) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 119.6(2) . . ?
C18 C13 N2 123.2(2) . . ?
C14 C13 N2 117.2(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.0(3) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 122.7(2) . . ?
C18 C17 Br3 118.5(2) . . ?
C16 C17 Br3 118.8(2) . . ?
C17 C18 C13 118.5(2) . . ?
C17 C18 H18 120.8 . . ?
C13 C18 H18 120.8 . . ?
C20 C19 C24 120.5(3) . . ?
C20 C19 S2 120.9(2) . . ?
C24 C19 S2 118.6(2) . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 Br4 118.6(2) . . ?
C21 C22 Br4 119.6(2) . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C19 119.7(3) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
N3 C25 C26 123.7(3) . . ?
N3 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C25 C26 C27 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 117.2(2) . . ?
C28 C27 C32 121.1(2) . . ?
C26 C27 C32 121.7(2) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
N3 C29 C28 123.7(3) . . ?
N3 C29 H29 118.1 . . ?
C28 C29 H29 118.1 . . ?
N4 C30 C31 123.3(2) . . ?
N4 C30 H30 118.3 . . ?
C31 C30 H30 118.3 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 116.8(2) . . ?
C31 C32 C27 121.5(2) . . ?
C33 C32 C27 121.7(2) . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
N4 C34 C33 123.4(3) . . ?
N4 C34 H34 118.3 . . ?
C33 C34 H34 118.3 . . ?
N5 C35 C36 124.4(3) . . ?
N5 C35 H35 117.8 . . ?
C36 C35 H35 117.8 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 116.1(3) . . ?
C36 C37 C42 121.8(3) . . ?
C38 C37 C42 122.1(3) . . ?
C39 C38 C37 119.2(3) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
N5 C39 C38 124.7(3) . . ?
N5 C39 H39 117.7 . . ?
C38 C39 H39 117.7 . . ?
N6 C40 C41 124.9(3) . . ?
N6 C40 H40 117.5 . . ?
C41 C40 H40 117.5 . . ?
C40 C41 C42 119.2(3) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
C43 C42 C41 116.3(3) . . ?
C43 C42 C37 122.0(3) . . ?
C41 C42 C37 121.7(3) . . ?
C42 C43 C44 119.9(3) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
N6 C44 C43 124.1(3) . . ?
N6 C44 H44 118.0 . . ?
C43 C44 H44 118.0 . . ?
N7 C45 C46 124.4(3) . . ?
N7 C45 H45 117.8 . . ?
C46 C45 H45 117.8 . . ?
C45 C46 C47 119.5(3) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C46 C47 C48 116.5(3) . . ?
C46 C47 C52 121.9(3) . . ?
C48 C47 C52 121.6(3) . . ?
C49 C48 C47 119.6(3) . . ?
C49 C48 H48 120.2 . . ?
C47 C48 H48 120.2 . . ?
N7 C49 C48 124.5(3) . . ?
N7 C49 H49 117.7 . . ?
C48 C49 H49 117.7 . . ?
N8 C50 C51 124.3(3) . . ?
N8 C50 H50 117.8 . . ?
C51 C50 H50 117.8 . . ?
C50 C51 C52 120.2(3) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
C51 C52 C53 116.1(3) . . ?
C51 C52 C47 122.0(3) . . ?
C53 C52 C47 121.9(3) . . ?
C54 C53 C52 119.5(3) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
N8 C54 C53 124.3(3) . . ?
N8 C54 H54 117.9 . . ?
C53 C54 H54 117.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.903(3) . ?
Br2 C10 1.892(3) . ?
Br3 C17 1.907(3) . ?
Br4 C22 1.898(3) . ?
S1 O1 1.4312(19) . ?
S1 O2 1.4376(19) . ?
S1 N1 1.630(2) . ?
S1 C7 1.760(3) . ?
S2 O3 1.4295(19) . ?
S2 O4 1.4354(19) . ?
S2 N2 1.633(2) . ?
S2 C19 1.763(3) . ?
N1 C1 1.426(3) . ?
N1 H1 0.75(3) . ?
N2 C13 1.421(3) . ?
N2 H2 0.80(3) . ?
N3 C29 1.334(4) . ?
N3 C25 1.336(4) . ?
N4 C30 1.339(3) . ?
N4 C34 1.341(3) . ?
N5 C35 1.320(4) . ?
N5 C39 1.338(4) . ?
N6 C44 1.323(4) . ?
N6 C40 1.337(4) . ?
N7 C49 1.334(4) . ?
N7 C45 1.342(4) . ?
N8 C50 1.337(4) . ?
N8 C54 1.338(4) . ?
C1 C6 1.393(4) . ?
C1 C2 1.397(4) . ?
C2 C3 1.390(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(4) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.393(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.389(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(4) . ?
C19 C24 1.395(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(4) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 C32 1.486(4) . ?
C28 C29 1.380(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.384(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(4) . ?
C33 C34 1.377(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.381(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.389(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.395(4) . ?
C37 C42 1.488(4) . ?
C38 C39 1.382(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.377(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.394(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.385(4) . ?
C43 C44 1.389(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.383(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.390(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.396(4) . ?
C47 C52 1.495(4) . ?
C48 C49 1.379(4) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C51 1.379(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.401(4) . ?
C53 C54 1.385(4) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N3 . . . 2.848(4) 0.75(3) 2.10(3) 176(3) no
N2 H2 N4 . . . 2.885(4) 0.80(4) 2.08(4) 178(3) no
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
O1 S1 N1 C1 -172.9(2) . . . . ?
O2 S1 N1 C1 58.3(2) . . . . ?
C7 S1 N1 C1 -57.8(2) . . . . ?
O3 S2 N2 C13 174.5(2) . . . . ?
O4 S2 N2 C13 -56.7(2) . . . . ?
C19 S2 N2 C13 59.9(2) . . . . ?
S1 N1 C1 C6 145.8(2) . . . . ?
S1 N1 C1 C2 -37.6(4) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
N1 C1 C2 C3 -176.6(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 Br1 179.57(19) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Br1 C3 C4 C5 -179.5(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
N1 C1 C6 C5 176.8(2) . . . . ?
O1 S1 C7 C12 -145.9(2) . . . . ?
O2 S1 C7 C12 -14.6(2) . . . . ?
N1 S1 C7 C12 101.7(2) . . . . ?
O1 S1 C7 C8 36.9(2) . . . . ?
O2 S1 C7 C8 168.2(2) . . . . ?
N1 S1 C7 C8 -75.5(2) . . . . ?
C12 C7 C8 C9 -2.6(4) . . . . ?
S1 C7 C8 C9 174.6(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 3.7(4) . . . . ?
C8 C9 C10 Br2 -175.9(2) . . . . ?
C9 C10 C11 C12 -4.0(4) . . . . ?
Br2 C10 C11 C12 175.6(2) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
C8 C7 C12 C11 2.2(4) . . . . ?
S1 C7 C12 C11 -174.9(2) . . . . ?
S2 N2 C13 C18 35.3(4) . . . . ?
S2 N2 C13 C14 -147.8(2) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
N2 C13 C14 C15 -177.4(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 1.6(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C15 C16 C17 Br3 178.9(2) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
Br3 C17 C18 C13 179.68(19) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
N2 C13 C18 C17 178.2(2) . . . . ?
O3 S2 C19 C20 146.6(2) . . . . ?
O4 S2 C19 C20 14.8(3) . . . . ?
N2 S2 C19 C20 -101.6(2) . . . . ?
O3 S2 C19 C24 -36.4(2) . . . . ?
O4 S2 C19 C24 -168.2(2) . . . . ?
N2 S2 C19 C24 75.4(2) . . . . ?
C24 C19 C20 C21 -1.5(4) . . . . ?
S2 C19 C20 C21 175.4(2) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C23 2.5(4) . . . . ?
C20 C21 C22 Br4 -176.9(2) . . . . ?
C21 C22 C23 C24 -2.3(4) . . . . ?
Br4 C22 C23 C24 177.0(2) . . . . ?
C22 C23 C24 C19 0.2(4) . . . . ?
C20 C19 C24 C23 1.6(4) . . . . ?
S2 C19 C24 C23 -175.4(2) . . . . ?
C29 N3 C25 C26 0.4(4) . . . . ?
N3 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C25 C26 C27 C32 -179.0(3) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C32 C27 C28 C29 178.4(2) . . . . ?
C25 N3 C29 C28 -1.2(4) . . . . ?
C27 C28 C29 N3 1.1(4) . . . . ?
C34 N4 C30 C31 0.4(4) . . . . ?
N4 C30 C31 C32 0.6(4) . . . . ?
C30 C31 C32 C33 -1.6(4) . . . . ?
C30 C31 C32 C27 177.7(2) . . . . ?
C28 C27 C32 C31 159.0(3) . . . . ?
C26 C27 C32 C31 -22.6(4) . . . . ?
C28 C27 C32 C33 -21.8(4) . . . . ?
C26 C27 C32 C33 156.6(3) . . . . ?
C31 C32 C33 C34 1.7(4) . . . . ?
C27 C32 C33 C34 -177.6(2) . . . . ?
C30 N4 C34 C33 -0.3(4) . . . . ?
C32 C33 C34 N4 -0.8(4) . . . . ?
C39 N5 C35 C36 0.7(5) . . . . ?
N5 C35 C36 C37 -0.7(5) . . . . ?
C35 C36 C37 C38 0.5(4) . . . . ?
C35 C36 C37 C42 -178.5(3) . . . . ?
C36 C37 C38 C39 -0.4(4) . . . . ?
C42 C37 C38 C39 178.7(3) . . . . ?
C35 N5 C39 C38 -0.6(5) . . . . ?
C37 C38 C39 N5 0.4(5) . . . . ?
C44 N6 C40 C41 0.1(5) . . . . ?
N6 C40 C41 C42 1.3(6) . . . . ?
C40 C41 C42 C43 -1.4(5) . . . . ?
C40 C41 C42 C37 177.8(3) . . . . ?
C36 C37 C42 C43 159.5(3) . . . . ?
C38 C37 C42 C43 -19.5(4) . . . . ?
C36 C37 C42 C41 -19.7(4) . . . . ?
C38 C37 C42 C41 161.3(3) . . . . ?
C41 C42 C43 C44 0.3(4) . . . . ?
C37 C42 C43 C44 -178.9(3) . . . . ?
C40 N6 C44 C43 -1.4(5) . . . . ?
C42 C43 C44 N6 1.2(5) . . . . ?
C49 N7 C45 C46 -0.2(4) . . . . ?
N7 C45 C46 C47 0.3(5) . . . . ?
C45 C46 C47 C48 -0.3(4) . . . . ?
C45 C46 C47 C52 178.4(3) . . . . ?
C46 C47 C48 C49 0.3(4) . . . . ?
C52 C47 C48 C49 -178.4(3) . . . . ?
C45 N7 C49 C48 0.3(5) . . . . ?
C47 C48 C49 N7 -0.3(5) . . . . ?
C54 N8 C50 C51 -1.2(5) . . . . ?
N8 C50 C51 C52 1.2(5) . . . . ?
C50 C51 C52 C53 -0.2(4) . . . . ?
C50 C51 C52 C47 -178.5(3) . . . . ?
C46 C47 C52 C51 -19.4(4) . . . . ?
C48 C47 C52 C51 159.2(3) . . . . ?
C46 C47 C52 C53 162.4(3) . . . . ?
C48 C47 C52 C53 -19.0(4) . . . . ?
C51 C52 C53 C54 -0.6(4) . . . . ?
C47 C52 C53 C54 177.7(3) . . . . ?
C50 N8 C54 C53 0.2(4) . . . . ?
C52 C53 C54 N8 0.7(5) . . . . ?
