#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:31:50 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290218 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/80/7248008.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_7248008
loop_
_publ_author_name
'Liu, Ya-Zhou'
'Chen, Yu'
'Wang, Amu'
'Shen, Zhongke'
'Zhou, Xueting'
'Zhang, Jichao'
'Jian, Yinxiang'
'Ma, Xiaofeng'
_publ_section_title
;
 An electron-donor--acceptor complex between two intermediates enables a
 N--N bond cleavage cascade process to access 2,3-difunctionalized
 pyridines
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              2280
_journal_page_last               2289
_journal_paper_doi               10.1039/D3GC04425D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 Br N2 O4 S2, C3 H6 O'
_chemical_formula_sum            'C24 H25 Br N2 O5 S2'
_chemical_formula_weight         565.49
_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
_audit_creation_date             2022-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                92.802(6)
_cell_angle_beta                 98.268(7)
_cell_angle_gamma                103.730(7)
_cell_formula_units_Z            2
_cell_length_a                   8.1423(8)
_cell_length_b                   12.2839(8)
_cell_length_c                   12.9853(9)
_cell_measurement_reflns_used    1959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2890
_cell_measurement_theta_min      3.3200
_cell_volume                     1243.89(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  49.00   1.00    2.25    --  -15.48  57.00 -60.00   51
  2  ω    -42.00  52.00   1.00    2.25    --  -15.48  77.00 150.00   94
  3  ω    -17.00  19.00   1.00    2.25    --  -15.48 -99.00 -60.00   36
  4  ω    -19.00  39.00   1.00    2.25    --  -15.48  57.00-150.00   58
  5  ω      3.00  79.00   1.00    2.25    --   17.66  57.00 -60.00   76
  6  ω     -8.00  85.00   1.00    2.25    --   17.66  77.00  60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208346000
_diffrn_orient_matrix_UB_12      -0.0573454000
_diffrn_orient_matrix_UB_13      0.0105406000
_diffrn_orient_matrix_UB_21      0.0129889000
_diffrn_orient_matrix_UB_22      0.0164513000
_diffrn_orient_matrix_UB_23      0.0542679000
_diffrn_orient_matrix_UB_31      -0.0874683000
_diffrn_orient_matrix_UB_32      0.0007814000
_diffrn_orient_matrix_UB_33      -0.0036688000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10277
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.182
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3207
_reflns_number_total             5093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc04425d2.cif
_cod_data_source_block           221011_s4_lyz
_cod_depositor_comments
'Adding full bibliography for 7248007--7248009.cif.'
_cod_database_code               7248008
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_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.
;
_shelx_estimated_absorpt_t_max   0.654
_shelx_estimated_absorpt_t_min   0.562
_diffrn_oxdiff_digest_frames
;
0127f5b8d7120ecf6fefb0bdba1d1d016000029311c
;
_diffrn_oxdiff_digest_hkl
;
01e62c10eb1c671a073b62e8949411a15be98b
;
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.802
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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 0.61686(6) 0.67646(4) 0.12954(3) 0.0655(2) Uani 1 1 d . . . . .
S1 S 0.68219(13) 0.29613(9) 0.48346(8) 0.0505(3) Uani 1 1 d . . . . .
O1 O 0.5278(3) 0.3126(2) 0.4258(2) 0.0659(9) Uani 1 1 d . . . . .
N1 N 0.8122(4) 0.5431(3) 0.3883(2) 0.0497(9) Uani 1 1 d . . . . .
C1 C 0.7024(5) 0.5766(3) 0.2172(3) 0.0431(9) Uani 1 1 d . . . . .
S2 S 0.74880(13) 0.21301(8) 0.12205(8) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.6896(4) 0.1840(2) 0.5052(2) 0.0670(9) Uani 1 1 d . . . . .
N2 N 0.7974(4) 0.2976(3) 0.2284(2) 0.0470(8) Uani 1 1 d . . . . .
C2 C 0.7569(5) 0.6104(3) 0.3212(3) 0.0497(10) Uani 1 1 d . . . . .
H2 H 0.755178 0.682520 0.345696 0.060 Uiso 1 1 calc R . . . .
O3 O 0.8749(3) 0.1495(2) 0.1289(2) 0.0580(8) Uani 1 1 d . . . . .
C3 C 0.8142(5) 0.4426(3) 0.3493(3) 0.0416(9) Uani 1 1 d . . . . .
O4 O 0.7283(4) 0.2807(2) 0.03784(19) 0.0563(8) Uani 1 1 d . . . . .
C4 C 0.8558(5) 0.3506(3) 0.4117(3) 0.0439(10) Uani 1 1 d . . . . .
H4 H 0.965274 0.377017 0.458857 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8653(5) 0.2608(3) 0.3280(3) 0.0507(11) Uani 1 1 d . . . . .
H5A H 0.982657 0.256029 0.328788 0.061 Uiso 1 1 calc R . . . .
H5B H 0.796670 0.187678 0.339681 0.061 Uiso 1 1 calc R . . . .
C6 C 0.7685(4) 0.4052(3) 0.2435(3) 0.0381(9) Uani 1 1 d . . . . .
C7 C 0.7074(5) 0.4727(3) 0.1745(3) 0.0422(9) Uani 1 1 d . . . . .
H7 H 0.671930 0.450028 0.103745 0.051 Uiso 1 1 calc R . . . .
C8 C 0.7290(5) 0.3782(3) 0.6021(3) 0.0469(10) Uani 1 1 d . . . . .
C9 C 0.6872(5) 0.4808(4) 0.6098(3) 0.0539(11) Uani 1 1 d . . . . .
H9 H 0.638283 0.508176 0.550519 0.065 Uiso 1 1 calc R . . . .
C10 C 0.7183(5) 0.5425(4) 0.7055(3) 0.0583(12) Uani 1 1 d . . . . .
H10 H 0.689187 0.611128 0.710282 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7919(5) 0.5035(4) 0.7943(3) 0.0567(11) Uani 1 1 d . . . . .
C12 C 0.8332(6) 0.4014(4) 0.7850(3) 0.0618(12) Uani 1 1 d . . . . .
H12 H 0.882112 0.374054 0.844276 0.074 Uiso 1 1 calc R . . . .
C13 C 0.8038(5) 0.3387(4) 0.6901(3) 0.0571(11) Uani 1 1 d . . . . .
H13 H 0.833960 0.270374 0.685503 0.069 Uiso 1 1 calc R . . . .
C14 C 0.8212(7) 0.5695(4) 0.8986(4) 0.0803(15) Uani 1 1 d . . . . .
H14A H 0.830619 0.647528 0.888595 0.120 Uiso 1 1 calc GR . . . .
H14B H 0.925098 0.561242 0.939252 0.120 Uiso 1 1 calc GR . . . .
H14C H 0.726727 0.541894 0.934664 0.120 Uiso 1 1 calc GR . . . .
C15 C 0.5510(5) 0.1209(3) 0.1285(3) 0.0407(9) Uani 1 1 d . . . . .
C16 C 0.5409(5) 0.0104(3) 0.1467(3) 0.0511(11) Uani 1 1 d . . . . .
H16 H 0.639831 -0.015667 0.156845 0.061 Uiso 1 1 calc R . . . .
C17 C 0.3848(5) -0.0614(4) 0.1498(3) 0.0567(11) Uani 1 1 d . . . . .
H17 H 0.378768 -0.136164 0.161636 0.068 Uiso 1 1 calc R . . . .
C18 C 0.2358(5) -0.0241(4) 0.1356(3) 0.0525(11) Uani 1 1 d . . . . .
C19 C 0.2516(6) 0.0878(4) 0.1172(4) 0.0631(13) Uani 1 1 d . . . . .
H19 H 0.153347 0.114595 0.106935 0.076 Uiso 1 1 calc R . . . .
C20 C 0.4052(5) 0.1599(4) 0.1136(3) 0.0558(11) Uani 1 1 d . . . . .
H20 H 0.411667 0.234628 0.101170 0.067 Uiso 1 1 calc R . . . .
C21 C 0.0647(5) -0.1022(4) 0.1375(4) 0.0741(14) Uani 1 1 d . . . . .
H21A H 0.057636 -0.172632 0.099471 0.111 Uiso 1 1 calc GR . . . .
H21B H -0.023999 -0.069522 0.105663 0.111 Uiso 1 1 calc GR . . . .
H21C H 0.050825 -0.114565 0.208464 0.111 Uiso 1 1 calc GR . . . .
O5 O 0.1018(5) 0.1693(3) 0.5054(3) 0.0982(13) Uani 1 1 d . . . . .
C22 C 0.2186(7) 0.0591(4) 0.3989(4) 0.0886(17) Uani 1 1 d . . . . .
H22A H 0.142457 0.078872 0.343510 0.133 Uiso 1 1 calc GR . . . .
H22B H 0.193381 -0.021299 0.399501 0.133 Uiso 1 1 calc GR . . . .
H22C H 0.334799 0.086961 0.388110 0.133 Uiso 1 1 calc GR . . . .
C23 C 0.1957(6) 0.1091(4) 0.4996(4) 0.0626(12) Uani 1 1 d . . . . .
C24 C 0.2932(7) 0.0788(4) 0.5950(4) 0.0864(17) Uani 1 1 d . . . . .
H24A H 0.273529 0.119107 0.655384 0.130 Uiso 1 1 calc GR . . . .
H24B H 0.413202 0.098220 0.590671 0.130 Uiso 1 1 calc GR . . . .
H24C H 0.255789 -0.000624 0.600587 0.130 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.42(18) . . ?
O1 S1 C4 107.81(18) . . ?
O1 S1 C8 108.86(18) . . ?
O2 S1 C4 107.16(18) . . ?
O2 S1 C8 107.71(19) . . ?
C8 S1 C4 106.26(18) . . ?
C3 N1 C2 116.5(3) . . ?
C2 C1 Br1 118.6(3) . . ?
C2 C1 C7 122.3(3) . . ?
C7 C1 Br1 119.1(3) . . ?
N2 S2 C15 106.43(17) . . ?
O3 S2 N2 105.53(16) . . ?
O3 S2 C15 107.96(18) . . ?
O4 S2 N2 106.43(16) . . ?
O4 S2 O3 120.70(18) . . ?
O4 S2 C15 108.92(17) . . ?
C5 N2 S2 120.8(2) . . ?
C6 N2 S2 128.4(2) . . ?
C6 N2 C5 110.5(3) . . ?
N1 C2 C1 122.0(3) . . ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C3 C4 125.3(3) . . ?
N1 C3 C6 124.2(3) . . ?
C6 C3 C4 110.5(3) . . ?
S1 C4 H4 111.3 . . ?
C3 C4 S1 109.4(3) . . ?
C3 C4 H4 111.3 . . ?
C3 C4 C5 103.3(3) . . ?
C5 C4 S1 110.1(3) . . ?
C5 C4 H4 111.3 . . ?
N2 C5 C4 105.3(3) . . ?
N2 C5 H5A 110.7 . . ?
N2 C5 H5B 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C3 C6 N2 109.1(3) . . ?
C7 C6 N2 131.3(3) . . ?
C7 C6 C3 119.6(3) . . ?
C1 C7 H7 122.3 . . ?
C6 C7 C1 115.3(3) . . ?
C6 C7 H7 122.3 . . ?
C9 C8 S1 120.7(3) . . ?
C13 C8 S1 119.5(3) . . ?
C13 C8 C9 119.7(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.7(4) . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 C14 121.0(4) . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.7(4) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S2 120.5(3) . . ?
C16 C15 C20 120.3(4) . . ?
C20 C15 S2 119.2(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 121.3(4) . . ?
C19 C18 C17 117.2(4) . . ?
C19 C18 C21 121.5(4) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.5(4) . . ?
C20 C19 H19 118.7 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.0(4) . . ?
C19 C20 H20 120.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
O5 C23 C22 122.3(5) . . ?
O5 C23 C24 121.1(5) . . ?
C22 C23 C24 116.6(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 C1 1.897(4) . ?
S1 O1 1.431(3) . ?
S1 O2 1.433(3) . ?
S1 C4 1.818(4) . ?
S1 C8 1.741(4) . ?
N1 C2 1.335(4) . ?
N1 C3 1.316(4) . ?
C1 C2 1.370(5) . ?
C1 C7 1.379(5) . ?
S2 N2 1.628(3) . ?
S2 O3 1.425(3) . ?
S2 O4 1.421(3) . ?
S2 C15 1.751(4) . ?
N2 C5 1.468(4) . ?
N2 C6 1.406(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.497(5) . ?
C3 C6 1.395(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.533(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.371(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 C13 1.381(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(6) . ?
C11 C12 1.378(6) . ?
C11 C14 1.503(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.374(5) . ?
C15 C20 1.375(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C18 C19 1.385(6) . ?
C18 C21 1.496(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.359(6) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O5 C23 1.189(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C23 1.473(6) . ?
C23 C24 1.485(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
Br1 C1 C2 N1 177.3(3) . . . . ?
Br1 C1 C7 C6 -179.0(3) . . . . ?
S1 C4 C5 N2 106.2(3) . . . . ?
S1 C8 C9 C10 177.0(3) . . . . ?
S1 C8 C13 C12 -176.9(3) . . . . ?
O1 S1 C4 C3 28.0(3) . . . . ?
O1 S1 C4 C5 -84.9(3) . . . . ?
O1 S1 C8 C9 -32.7(4) . . . . ?
O1 S1 C8 C13 145.1(3) . . . . ?
N1 C3 C4 S1 70.8(4) . . . . ?
N1 C3 C4 C5 -171.9(4) . . . . ?
N1 C3 C6 N2 175.7(4) . . . . ?
N1 C3 C6 C7 -4.0(6) . . . . ?
S2 N2 C5 C4 -167.4(3) . . . . ?
S2 N2 C6 C3 173.8(3) . . . . ?
S2 N2 C6 C7 -6.5(6) . . . . ?
S2 C15 C16 C17 -178.9(3) . . . . ?
S2 C15 C20 C19 179.1(3) . . . . ?
O2 S1 C4 C3 156.5(3) . . . . ?
O2 S1 C4 C5 43.6(3) . . . . ?
O2 S1 C8 C9 -162.3(3) . . . . ?
O2 S1 C8 C13 15.6(4) . . . . ?
N2 S2 C15 C16 -107.8(3) . . . . ?
N2 S2 C15 C20 73.2(3) . . . . ?
N2 C6 C7 C1 -177.5(4) . . . . ?
C2 N1 C3 C4 -174.1(4) . . . . ?
C2 N1 C3 C6 2.3(6) . . . . ?
C2 C1 C7 C6 0.8(6) . . . . ?
O3 S2 N2 C5 -36.7(3) . . . . ?
O3 S2 N2 C6 150.1(3) . . . . ?
O3 S2 C15 C16 5.1(4) . . . . ?
O3 S2 C15 C20 -173.9(3) . . . . ?
C3 N1 C2 C1 0.9(6) . . . . ?
C3 C4 C5 N2 -10.6(4) . . . . ?
C3 C6 C7 C1 2.2(5) . . . . ?
O4 S2 N2 C5 -166.1(3) . . . . ?
O4 S2 N2 C6 20.7(4) . . . . ?
O4 S2 C15 C16 137.8(3) . . . . ?
O4 S2 C15 C20 -41.2(4) . . . . ?
C4 S1 C8 C9 83.1(4) . . . . ?
C4 S1 C8 C13 -99.0(4) . . . . ?
C4 C3 C6 N2 -7.4(4) . . . . ?
C4 C3 C6 C7 172.8(3) . . . . ?
C5 N2 C6 C3 0.1(4) . . . . ?
C5 N2 C6 C7 179.8(4) . . . . ?
C6 N2 C5 C4 6.9(4) . . . . ?
C6 C3 C4 S1 -106.0(3) . . . . ?
C6 C3 C4 C5 11.2(4) . . . . ?
C7 C1 C2 N1 -2.6(6) . . . . ?
C8 S1 C4 C3 -88.6(3) . . . . ?
C8 S1 C4 C5 158.5(3) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C8 C13 C12 1.0(6) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C9 C10 C11 C14 -178.4(4) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 C8 -0.8(7) . . . . ?
C13 C8 C9 C10 -0.8(6) . . . . ?
C14 C11 C12 C13 178.6(4) . . . . ?
C15 S2 N2 C5 77.9(3) . . . . ?
C15 S2 N2 C6 -95.3(4) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C16 C17 C18 C21 179.2(4) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C18 C19 C20 C15 0.1(7) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
C21 C18 C19 C20 -179.0(4) . . . . ?
