#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:38:18 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133763.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_7133763
loop_
_publ_author_name
'Dillon, Alexandra M.'
'Shtukenberg, Alexander G.'
'Demkiw, Krystyna M.'
'Woerpel, K. A.'
'Ward, Michael D.'
_publ_section_title
;
 Hydrogen-bonded frameworks for conformational analysis of reactive
 substrates.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11770
_journal_page_last               11773
_journal_paper_doi               10.1039/d4cc03430a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C23 H33 Br N6 O9 S2'
_chemical_formula_weight         681.58
_chemical_name_systematic
'guanidinium 4,4?-biphenyldisulfonate 2-bromopropiophenone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.032(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.674(3)
_cell_length_b                   11.6225(12)
_cell_length_c                   8.2592(8)
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      22.83
_cell_measurement_theta_min      2.62
_cell_volume                     2984.3(5)
_computing_cell_refinement       'Bruker APEX4'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 SMART APEXII'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.1323
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21396
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.87
_diffrn_source                   Incoatec
_diffrn_source_type              'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.69
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.059
_refine_diff_density_min         -1.169
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7077
_refine_ls_number_restraints     661
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0831
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0578P)²+15.6818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1996
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                4459
_reflns_number_total             7077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03430a2.cif
_cod_data_source_block           23mdw67d
_cod_depositor_comments
'Adding full bibliography for 7133757--7133764.cif.'
_cod_database_code               7133763
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
Br Br1A 0.44555(10) 0.2728(2) 0.1550(3) 0.0689(10) Uani d U P D 0.707(6) A 1
C C22A 0.4586(5) 0.4045(14) 0.3047(17) 0.023(2) Uani d U P D 0.707(6) A 1
H H22A 0.465875 0.374573 0.420158 0.028000 Uiso calc U P R 0.707(6) A 1
C C21A 0.4199(5) 0.4842(14) 0.2921(18) 0.023(2) Uani d U P D 0.707(6) A 1
H H21A 0.426492 0.545432 0.374652 0.035000 Uiso calc U P R 0.707(6) A 1
H H21B 0.395040 0.440109 0.312064 0.035000 Uiso calc U P R 0.707(6) A 1
H H21C 0.413358 0.518228 0.181616 0.035000 Uiso calc U P R 0.707(6) A 1
C C23A 0.4988(5) 0.4586(15) 0.263(2) 0.033(3) Uani d U P D 0.707(6) A 1
O O7A 0.4953(4) 0.5414(13) 0.1755(16) 0.054(4) Uani d U P D 0.707(6) A 1
C C18A 0.5430(3) 0.4085(11) 0.3283(17) 0.033(3) Uani d U P DG 0.707(6) A 1
C C15A 0.5779(4) 0.4775(11) 0.314(2) 0.072(6) Uani d U P DG 0.707(6) A 1
H H15A 0.573437 0.548788 0.256463 0.086000 Uiso calc U P R 0.707(6) A 1
C C16A 0.6194(3) 0.4423(14) 0.382(2) 0.094(5) Uani d U P DG 0.707(6) A 1
H H16A 0.643295 0.489454 0.372164 0.112000 Uiso calc U P R 0.707(6) A 1
C C17A 0.6260(3) 0.3380(15) 0.466(2) 0.094(5) Uani d U P DG 0.707(6) A 1
H H17A 0.654391 0.313944 0.512691 0.112000 Uiso calc U P R 0.707(6) A 1
C C19A 0.5911(5) 0.2690(10) 0.4805(19) 0.063(5) Uani d U P DG 0.707(6) A 1
H H19A 0.595630 0.197766 0.537517 0.076000 Uiso calc U P R 0.707(6) A 1
C C20A 0.5496(4) 0.3043(9) 0.4117(17) 0.048(4) Uani d U P DG 0.707(6) A 1
H H20A 0.525771 0.257098 0.421816 0.057000 Uiso calc U P R 0.707(6) A 1
Br Br1B 0.4744(4) 0.2006(8) 0.2329(16) 0.132(6) Uani d U P D 0.293(6) A 2
C C22B 0.4776(11) 0.359(2) 0.314(4) 0.034(6) Uani d U P D 0.293(6) A 2
H H22B 0.488812 0.354444 0.435265 0.041000 Uiso calc U P R 0.293(6) A 2
C C21B 0.4360(11) 0.437(3) 0.291(4) 0.023(2) Uani d U P D 0.293(6) A 2
H H21D 0.440591 0.499273 0.372465 0.035000 Uiso calc U P R 0.293(6) A 2
H H21E 0.411448 0.389978 0.308008 0.035000 Uiso calc U P R 0.293(6) A 2
H H21F 0.430182 0.469210 0.179841 0.035000 Uiso calc U P R 0.293(6) A 2
C C23B 0.5136(9) 0.410(3) 0.239(4) 0.037(6) Uani d U P D 0.293(6) A 2
O O7B 0.5038(10) 0.445(3) 0.101(3) 0.054(4) Uani d U P D 0.293(6) A 2
C C18B 0.5605(7) 0.406(3) 0.321(4) 0.033(3) Uani d U P DG 0.293(6) A 2
C C15B 0.5855(9) 0.492(3) 0.271(4) 0.072(6) Uani d U P DG 0.293(6) A 2
H H15B 0.574038 0.538051 0.177358 0.086000 Uiso calc U P R 0.293(6) A 2
C C16B 0.6271(9) 0.511(3) 0.356(5) 0.094(5) Uani d U P DG 0.293(6) A 2
H H16B 0.644167 0.569987 0.321379 0.112000 Uiso calc U P R 0.293(6) A 2
C C17B 0.6438(7) 0.444(4) 0.492(4) 0.069(9) Uani d U P DG 0.293(6) A 2
H H17B 0.672311 0.456708 0.550925 0.082000 Uiso calc U P R 0.293(6) A 2
C C19B 0.6189(10) 0.357(3) 0.543(4) 0.078(10) Uani d U P DG 0.293(6) A 2
H H19B 0.630326 0.311492 0.636451 0.094000 Uiso calc U P R 0.293(6) A 2
C C20B 0.5772(10) 0.339(3) 0.458(4) 0.072(10) Uani d U P DG 0.293(6) A 2
H H20B 0.560196 0.279555 0.492432 0.087000 Uiso calc U P R 0.293(6) A 2
S S1 0.69383(8) 0.1573(2) 1.0360(2) 0.0148(5) Uani d . . . 1.000000 . .
S S2 0.36381(8) 0.1527(2) 0.4714(2) 0.0138(5) Uani d . . . 1.000000 . .
O O1 0.7169(2) 0.1154(6) 0.9103(8) 0.0173(15) Uani d . . . 1.000000 . .
O O2 0.7019(2) 0.0868(6) 1.1820(8) 0.0165(15) Uani d . . . 1.000000 . .
O O3 0.7014(2) 0.2798(6) 1.0754(9) 0.0222(17) Uani d . . . 1.000000 . .
O O4 0.3581(2) 0.0788(6) 0.3245(9) 0.0206(17) Uani d . . . 1.000000 . .
O O5 0.3380(2) 0.1169(6) 0.5911(9) 0.0213(16) Uani d . . . 1.000000 . .
O O6 0.3575(2) 0.2734(6) 0.4328(8) 0.0201(16) Uani d . . . 1.000000 . .
C C1 0.6379(3) 0.1437(8) 0.9529(13) 0.018(2) Uani d U . D 1.000000 . .
C C4 0.5509(3) 0.1308(8) 0.8160(11) 0.0144(17) Uani d U . D 1.000000 . .
C C5A 0.5645(7) 0.1982(18) 0.955(2) 0.020(4) Uani d U P D 0.46(2) B 1
H H5A 0.544253 0.238840 1.004039 0.024000 Uiso calc U P R 0.46(2) B 1
C C6A 0.6086(6) 0.2053(19) 1.021(3) 0.019(4) Uani d U P D 0.46(2) B 1
H H6A 0.618280 0.253293 1.113505 0.022000 Uiso calc U P R 0.46(2) B 1
C C2A 0.6247(7) 0.074(2) 0.817(3) 0.020(6) Uani d U P D 0.46(2) B 1
H H2A 0.645066 0.032403 0.769597 0.023000 Uiso calc U P R 0.46(2) B 1
C C3A 0.5802(6) 0.0670(18) 0.749(3) 0.0144(17) Uani d U P D 0.46(2) B 1
H H3A 0.570419 0.017994 0.657593 0.017000 Uiso calc U P R 0.46(2) B 1
C C5B 0.5669(6) 0.2266(15) 0.904(2) 0.020(4) Uani d U P D 0.54(2) B 2
H H5B 0.548035 0.287127 0.921380 0.024000 Uiso calc U P R 0.54(2) B 2
C C6B 0.6107(6) 0.2348(15) 0.969(3) 0.019(4) Uani d U P D 0.54(2) B 2
H H6B 0.622050 0.302944 1.024358 0.022000 Uiso calc U P R 0.54(2) B 2
C C2B 0.6222(6) 0.0492(15) 0.859(3) 0.012(5) Uani d U P D 0.54(2) B 2
H H2B 0.641481 -0.009341 0.838470 0.015000 Uiso calc U P R 0.54(2) B 2
C C3B 0.5777(5) 0.0389(15) 0.794(2) 0.0144(17) Uani d U P D 0.54(2) B 2
H H3B 0.566324 -0.028464 0.736411 0.017000 Uiso calc U P R 0.54(2) B 2
C C7 0.5044(3) 0.1282(8) 0.7349(11) 0.0150(19) Uani d U . D 1.000000 . .
C C10 0.4177(3) 0.1401(9) 0.5732(13) 0.018(2) Uani d U . D 1.000000 . .
C C8A 0.4889(5) 0.0675(13) 0.589(2) 0.016(4) Uani d U P D 0.561(17) C 1
H H8A 0.508596 0.021583 0.543419 0.020000 Uiso calc U P R 0.561(17) C 1
C C9A 0.4466(5) 0.0708(15) 0.507(2) 0.016(4) Uani d U P D 0.561(17) C 1
H H9A 0.437304 0.027606 0.409088 0.019000 Uiso calc U P R 0.561(17) C 1
C C11A 0.4320(5) 0.1956(16) 0.721(2) 0.020(4) Uani d U P D 0.561(17) C 1
H H11A 0.412311 0.237491 0.771803 0.024000 Uiso calc U P R 0.561(17) C 1
C C12A 0.4743(5) 0.1908(14) 0.795(2) 0.015(3) Uani d U P D 0.561(17) C 1
H H12A 0.483275 0.233428 0.893524 0.018000 Uiso calc U P R 0.561(17) C 1
C C8B 0.4845(6) 0.0366(17) 0.645(3) 0.018(5) Uani d U P D 0.439(17) C 2
H H8B 0.500476 -0.031658 0.637126 0.022000 Uiso calc U P R 0.439(17) C 2
C C9B 0.4422(6) 0.0417(17) 0.567(3) 0.020(6) Uani d U P D 0.439(17) C 2
H H9B 0.429443 -0.023487 0.507709 0.024000 Uiso calc U P R 0.439(17) C 2
C C11B 0.4374(7) 0.2359(18) 0.663(3) 0.025(5) Uani d U P D 0.439(17) C 2
H H11B 0.421387 0.304306 0.669983 0.030000 Uiso calc U P R 0.439(17) C 2
C C12B 0.4796(6) 0.2294(16) 0.740(3) 0.015(3) Uani d U P D 0.439(17) C 2
H H12B 0.492675 0.294414 0.799314 0.018000 Uiso calc U P R 0.439(17) C 2
O O8 0.3026(2) 0.4620(7) 0.4340(10) 0.0229(17) Uani d . . D 1.000000 . .
H H1 0.318(3) 0.405(7) 0.415(15) 0.034000 Uiso d U . D 1.000000 . .
H H1E 0.2779(17) 0.430(9) 0.415(15) 0.034000 Uiso d U . D 1.000000 . .
O O9 0.7562(2) 0.5317(6) 0.5778(12) 0.029(2) Uani d . . D 1.000000 . .
H H1D 0.741(3) 0.591(6) 0.588(16) 0.043000 Uiso d U . D 1.000000 . .
H H1C 0.7830(10) 0.543(11) 0.582(17) 0.043000 Uiso d U . D 1.000000 . .
N N4 0.7187(3) 0.1438(7) 0.5378(11) 0.0194(19) Uani d . . . 1.000000 . .
H H4A 0.716373 0.101754 0.624257 0.023000 Uiso calc U . R 1.000000 . .
H H4B 0.712479 0.113810 0.438220 0.023000 Uiso calc U . R 1.000000 . .
N N5 0.7351(3) 0.3162(7) 0.4259(10) 0.0182(19) Uani d . . . 1.000000 . .
H H5C 0.743593 0.388319 0.437945 0.022000 Uiso calc U . R 1.000000 . .
H H5D 0.728805 0.285640 0.326690 0.022000 Uiso calc U . R 1.000000 . .
N N6 0.7413(3) 0.3012(7) 0.7035(10) 0.0208(19) Uani d . . . 1.000000 . .
H H6C 0.749713 0.373427 0.712949 0.025000 Uiso calc U . R 1.000000 . .
H H6D 0.739243 0.261148 0.792095 0.025000 Uiso calc U . R 1.000000 . .
C C14 0.7317(3) 0.2534(9) 0.5577(13) 0.018(2) Uani d . . . 1.000000 . .
N N1 0.3242(3) 0.6937(8) 0.3045(10) 0.023(2) Uani d . . . 1.000000 . .
H H1A 0.315927 0.621367 0.292815 0.027000 Uiso calc U . R 1.000000 . .
H H1B 0.326353 0.735020 0.217174 0.027000 Uiso calc U . R 1.000000 . .
N N2 0.3300(3) 0.6769(8) 0.5830(11) 0.022(2) Uani d . . . 1.000000 . .
H H2C 0.336080 0.706821 0.682682 0.026000 Uiso calc U . R 1.000000 . .
H H2D 0.321691 0.604776 0.569639 0.026000 Uiso calc U . R 1.000000 . .
N N3 0.3459(3) 0.8490(7) 0.4717(10) 0.0192(19) Uani d . . . 1.000000 . .
H H3C 0.352067 0.879725 0.570817 0.023000 Uiso calc U . R 1.000000 . .
H H3D 0.348104 0.890491 0.384591 0.023000 Uiso calc U . R 1.000000 . .
C C13 0.3334(3) 0.7403(8) 0.4538(12) 0.017(2) Uani d . . . 1.000000 . .
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23A C22A C21A . . 115.6(13) ?
C23A C22A Br1A . . 105.3(10) ?
C21A C22A Br1A . . 111.2(10) ?
C23A C22A H22A . . 108.200000 ?
C21A C22A H22A . . 108.200000 ?
Br1A C22A H22A . . 108.200000 ?
C22A C21A H21A . . 109.500000 ?
C22A C21A H21B . . 109.500000 ?
H21A C21A H21B . . 109.500000 ?
C22A C21A H21C . . 109.500000 ?
H21A C21A H21C . . 109.500000 ?
H21B C21A H21C . . 109.500000 ?
O7A C23A C18A . . 119.8(14) ?
O7A C23A C22A . . 119.1(16) ?
C18A C23A C22A . . 121.1(14) ?
C15A C18A C20A . . 120.000000 ?
C15A C18A C23A . . 116.2(10) ?
C20A C18A C23A . . 123.5(10) ?
C16A C15A C18A . . 120.000000 ?
C16A C15A H15A . . 120.000000 ?
C18A C15A H15A . . 120.000000 ?
C15A C16A C17A . . 120.000000 ?
C15A C16A H16A . . 120.000000 ?
C17A C16A H16A . . 120.000000 ?
C16A C17A C19A . . 120.000000 ?
C16A C17A H17A . . 120.000000 ?
C19A C17A H17A . . 120.000000 ?
C20A C19A C17A . . 120.000000 ?
C20A C19A H19A . . 120.000000 ?
C17A C19A H19A . . 120.000000 ?
C19A C20A C18A . . 120.000000 ?
C19A C20A H20A . . 120.000000 ?
C18A C20A H20A . . 120.000000 ?
C23B C22B C21B . . 114.(3) ?
C23B C22B Br1B . . 103.(2) ?
C21B C22B Br1B . . 121.(2) ?
C23B C22B H22B . . 106.100000 ?
C21B C22B H22B . . 106.100000 ?
Br1B C22B H22B . . 106.100000 ?
C22B C21B H21D . . 109.500000 ?
C22B C21B H21E . . 109.500000 ?
H21D C21B H21E . . 109.500000 ?
C22B C21B H21F . . 109.500000 ?
H21D C21B H21F . . 109.500000 ?
H21E C21B H21F . . 109.500000 ?
O7B C23B C18B . . 120.(3) ?
O7B C23B C22B . . 116.(3) ?
C18B C23B C22B . . 124.(3) ?
C15B C18B C20B . . 120.000000 ?
C15B C18B C23B . . 114.(2) ?
C20B C18B C23B . . 125.(2) ?
C18B C15B C16B . . 120.000000 ?
C18B C15B H15B . . 120.000000 ?
C16B C15B H15B . . 120.000000 ?
C17B C16B C15B . . 120.000000 ?
C17B C16B H16B . . 120.000000 ?
C15B C16B H16B . . 120.000000 ?
C16B C17B C19B . . 120.000000 ?
C16B C17B H17B . . 120.000000 ?
C19B C17B H17B . . 120.000000 ?
C20B C19B C17B . . 120.000000 ?
C20B C19B H19B . . 120.000000 ?
C17B C19B H19B . . 120.000000 ?
C19B C20B C18B . . 120.000000 ?
C19B C20B H20B . . 120.000000 ?
C18B C20B H20B . . 120.000000 ?
O2 S1 O1 . . 111.9(4) ?
O2 S1 O3 . . 111.7(4) ?
O1 S1 O3 . . 113.4(4) ?
O2 S1 C1 . . 106.0(5) ?
O1 S1 C1 . . 107.0(5) ?
O3 S1 C1 . . 106.3(4) ?
O6 S2 O5 . . 110.8(4) ?
O6 S2 O4 . . 113.3(4) ?
O5 S2 O4 . . 113.3(4) ?
O6 S2 C10 . . 105.5(5) ?
O5 S2 C10 . . 105.7(5) ?
O4 S2 C10 . . 107.5(5) ?
C6A C1 C2A . . 120.9(15) ?
C2B C1 C6B . . 120.0(13) ?
C6A C1 S1 . . 119.8(11) ?
C2B C1 S1 . . 120.7(10) ?
C2A C1 S1 . . 119.2(11) ?
C6B C1 S1 . . 119.0(10) ?
C3A C4 C5A . . 120.5(14) ?
C5B C4 C3B . . 121.3(13) ?
C5B C4 C7 . . 119.0(11) ?
C3A C4 C7 . . 119.2(11) ?
C5A C4 C7 . . 120.3(12) ?
C3B C4 C7 . . 119.7(11) ?
C4 C5A C6A . . 119.0(18) ?
C4 C5A H5A . . 120.500000 ?
C6A C5A H5A . . 120.500000 ?
C1 C6A C5A . . 120.7(18) ?
C1 C6A H6A . . 119.700000 ?
C5A C6A H6A . . 119.700000 ?
C1 C2A C3A . . 118.6(18) ?
C1 C2A H2A . . 120.700000 ?
C3A C2A H2A . . 120.700000 ?
C4 C3A C2A . . 120.2(16) ?
C4 C3A H3A . . 119.900000 ?
C2A C3A H3A . . 119.900000 ?
C4 C5B C6B . . 119.8(15) ?
C4 C5B H5B . . 120.100000 ?
C6B C5B H5B . . 120.100000 ?
C1 C6B C5B . . 120.2(15) ?
C1 C6B H6B . . 119.900000 ?
C5B C6B H6B . . 119.900000 ?
C1 C2B C3B . . 120.3(15) ?
C1 C2B H2B . . 119.800000 ?
C3B C2B H2B . . 119.800000 ?
C4 C3B C2B . . 118.1(14) ?
C4 C3B H3B . . 121.000000 ?
C2B C3B H3B . . 121.000000 ?
C12A C7 C8A . . 115.1(12) ?
C8B C7 C12B . . 117.2(13) ?
C12A C7 C4 . . 121.6(10) ?
C8B C7 C4 . . 124.5(12) ?
C8A C7 C4 . . 123.2(10) ?
C12B C7 C4 . . 118.2(11) ?
C11A C10 C9A . . 119.0(13) ?
C9B C10 C11B . . 118.3(14) ?
C11A C10 S2 . . 120.6(10) ?
C9B C10 S2 . . 123.4(11) ?
C9A C10 S2 . . 120.5(10) ?
C11B C10 S2 . . 118.3(10) ?
C9A C8A C7 . . 123.6(14) ?
C9A C8A H8A . . 118.200000 ?
C7 C8A H8A . . 118.200000 ?
C8A C9A C10 . . 118.0(14) ?
C8A C9A H9A . . 121.000000 ?
C10 C9A H9A . . 121.000000 ?
C12A C11A C10 . . 120.4(14) ?
C12A C11A H11A . . 119.800000 ?
C10 C11A H11A . . 119.800000 ?
C11A C12A C7 . . 123.8(14) ?
C11A C12A H12A . . 118.100000 ?
C7 C12A H12A . . 118.100000 ?
C9B C8B C7 . . 121.6(17) ?
C9B C8B H8B . . 119.200000 ?
C7 C8B H8B . . 119.200000 ?
C8B C9B C10 . . 121.4(18) ?
C8B C9B H9B . . 119.300000 ?
C10 C9B H9B . . 119.300000 ?
C12B C11B C10 . . 119.5(16) ?
C12B C11B H11B . . 120.200000 ?
C10 C11B H11B . . 120.200000 ?
C11B C12B C7 . . 121.9(16) ?
C11B C12B H12B . . 119.000000 ?
C7 C12B H12B . . 119.000000 ?
H1 O8 H1E . . 99.(10) ?
H1D O9 H1C . . 116.(10) ?
C14 N4 H4A . . 120.000000 ?
C14 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C14 N5 H5C . . 120.000000 ?
C14 N5 H5D . . 120.000000 ?
H5C N5 H5D . . 120.000000 ?
C14 N6 H6C . . 120.000000 ?
C14 N6 H6D . . 120.000000 ?
H6C N6 H6D . . 120.000000 ?
N6 C14 N5 . . 118.6(9) ?
N6 C14 N4 . . 121.9(9) ?
N5 C14 N4 . . 119.5(10) ?
C13 N1 H1A . . 120.000000 ?
C13 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C13 N2 H2C . . 120.000000 ?
C13 N2 H2D . . 120.000000 ?
H2C N2 H2D . . 120.000000 ?
C13 N3 H3C . . 120.000000 ?
C13 N3 H3D . . 120.000000 ?
H3C N3 H3D . . 120.000000 ?
N2 C13 N3 . . 120.8(9) ?
N2 C13 N1 . . 119.1(10) ?
N3 C13 N1 . . 120.2(9) ?
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
Br1A C22A . 1.962(15) ?
C22A C23A . 1.519(18) ?
C22A C21A . 1.52(2) ?
C22A H22A . 1.000000 ?
C21A H21A . 0.980000 ?
C21A H21B . 0.980000 ?
C21A H21C . 0.980000 ?
C23A O7A . 1.19(2) ?
C23A C18A . 1.52(2) ?
C18A C15A . 1.390000 ?
C18A C20A . 1.390000 ?
C15A C16A . 1.390000 ?
C15A H15A . 0.950000 ?
C16A C17A . 1.390000 ?
C16A H16A . 0.950000 ?
C17A C19A . 1.390000 ?
C17A H17A . 0.950000 ?
C19A C20A . 1.390000 ?
C19A H19A . 0.950000 ?
C20A H20A . 0.950000 ?
Br1B C22B . 1.96(3) ?
C22B C23B . 1.52(3) ?
C22B C21B . 1.58(3) ?
C22B H22B . 1.000000 ?
C21B H21D . 0.980000 ?
C21B H21E . 0.980000 ?
C21B H21F . 0.980000 ?
C23B O7B . 1.20(3) ?
C23B C18B . 1.51(3) ?
C18B C15B . 1.390000 ?
C18B C20B . 1.390000 ?
C15B C16B . 1.390000 ?
C15B H15B . 0.950000 ?
C16B C17B . 1.390000 ?
C16B H16B . 0.950000 ?
C17B C19B . 1.390000 ?
C17B H17B . 0.950000 ?
C19B C20B . 1.390000 ?
C19B H19B . 0.950000 ?
C20B H20B . 0.950000 ?
S1 O2 . 1.439(7) ?
S1 O1 . 1.463(7) ?
S1 O3 . 1.470(7) ?
S1 C1 . 1.781(11) ?
S2 O6 . 1.444(7) ?
S2 O5 . 1.459(7) ?
S2 O4 . 1.470(7) ?
S2 C10 . 1.759(11) ?
C1 C6A . 1.37(2) ?
C1 C2B . 1.380(18) ?
C1 C2A . 1.38(2) ?
C1 C6B . 1.386(18) ?
C4 C5B . 1.373(18) ?
C4 C3A . 1.382(18) ?
C4 C5A . 1.39(2) ?
C4 C3B . 1.397(16) ?
C4 C7 . 1.497(11) ?
C5A C6A . 1.40(2) ?
C5A H5A . 0.950000 ?
C6A H6A . 0.950000 ?
C2A C3A . 1.42(2) ?
C2A H2A . 0.950000 ?
C3A H3A . 0.950000 ?
C5B C6B . 1.392(19) ?
C5B H5B . 0.950000 ?
C6B H6B . 0.950000 ?
C2B C3B . 1.416(19) ?
C2B H2B . 0.950000 ?
C3B H3B . 0.950000 ?
C7 C12A . 1.367(16) ?
C7 C8B . 1.38(2) ?
C7 C8A . 1.404(18) ?
C7 C12B . 1.420(19) ?
C10 C11A . 1.380(18) ?
C10 C9B . 1.388(19) ?
C10 C9A . 1.405(17) ?
C10 C11B . 1.42(2) ?
C8A C9A . 1.380(19) ?
C8A H8A . 0.950000 ?
C9A H9A . 0.950000 ?
C11A C12A . 1.36(2) ?
C11A H11A . 0.950000 ?
C12A H12A . 0.950000 ?
C8B C9B . 1.37(2) ?
C8B H8B . 0.950000 ?
C9B H9B . 0.950000 ?
C11B C12B . 1.37(2) ?
C11B H11B . 0.950000 ?
C12B H12B . 0.950000 ?
O8 H1 . 0.846(15) ?
O8 H1E . 0.852(14) ?
O9 H1D . 0.849(14) ?
O9 H1C . 0.851(15) ?
N4 C14 . 1.339(13) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C14 . 1.332(12) ?
N5 H5C . 0.880000 ?
N5 H5D . 0.880000 ?
N6 C14 . 1.308(13) ?
N6 H6C . 0.880000 ?
N6 H6D . 0.880000 ?
N1 C13 . 1.327(12) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C13 . 1.319(13) ?
N2 H2C . 0.880000 ?
N2 H2D . 0.880000 ?
N3 C13 . 1.323(12) ?
N3 H3C . 0.880000 ?
N3 H3D . 0.880000 ?
