#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:24:11 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/24/7132423.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_7132423
loop_
_publ_author_name
'Feng, Guang-Chao'
'Li, Jun-Chi'
'Huang, Xiang'
'Liu, Ji-Kai'
'Wu, Bin'
'Yang, Jin-Ming'
_publ_section_title
;
 Cascade hydroarylation/Diels-Alder cycloaddition of alkynylindoles with
 electron-deficient alkynes and alkenes.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              328
_journal_page_last               331
_journal_paper_doi               10.1039/d3cc05210a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C30 H25 Br2 N3 O4 S'
_chemical_formula_sum            'C30 H25 Br2 N3 O4 S'
_chemical_formula_weight         683.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-24
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-12 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.922(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8975(8)
_cell_length_b                   9.0370(2)
_cell_length_c                   31.2449(14)
_cell_measurement_reflns_used    4674
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.5550
_cell_measurement_theta_min      4.4260
_cell_volume                     5581.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  24.00   1.00    2.00    --  -40.98  37.00  30.00   88
  2  ω     34.00  94.00   1.00    2.00    --   40.98-125.00  90.00   60
  3  ω     71.00  97.00   1.00    5.00    --  107.58 -94.00 -30.00   26
  4  ω     90.00 134.00   1.00    5.00    --  107.58-149.00 -50.00   44
  5  ω     52.00  95.00   1.00    2.00    --   40.98-125.00 -60.00   43
  6  ω     45.00 104.00   1.00    5.00    --  107.58 -94.00  30.00   59
  7  ω     48.00 115.00   1.00    5.00    --  107.58 -45.00   0.00   67
  8  ω     79.00 178.00   1.00    5.00    --  107.58  30.00  60.00   99
  9  ω    153.00 178.00   1.00    5.00    --  107.58 125.00 -90.00   25
 10  ω    146.00 177.00   1.00    5.00    --  107.58 125.00-120.00   31
 11  ω     94.00 120.00   1.00    5.00    --  107.58 125.00 -90.00   26
 12  ω     94.00 123.00   1.00    5.00    --  107.58 125.00 -60.00   29
 13  ω     97.00 129.00   1.00    5.00    --  107.58 125.00-120.00   32
 14  ω     94.00 175.00   1.00    5.00    --  107.58 125.00 -30.00   81
 15  ω     58.00  84.00   1.00    5.00    --  107.58 -30.00 150.00   26
 16  ω     36.00 102.00   1.00    5.00    --  107.58 -45.00  90.00   66
 17  ω     31.00 121.00   1.00    5.00    --  107.58 -30.00-120.00   90
 18  ω     34.00 130.00   1.00    5.00    --  107.58 -77.00-120.00   96
 19  ω    -99.00 -73.00   1.00    2.00    --  -40.98-149.00 -50.00   26
 20  ω   -113.00 -17.00   1.00    2.00    --  -40.98 -37.00-150.00   96
 21  ω   -115.00 -24.00   1.00    2.00    --  -40.98 -37.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0320911500
_diffrn_orient_matrix_UB_12      -0.0152683500
_diffrn_orient_matrix_UB_13      -0.0377623500
_diffrn_orient_matrix_UB_21      -0.0708609500
_diffrn_orient_matrix_UB_22      0.0050118500
_diffrn_orient_matrix_UB_23      -0.0358637500
_diffrn_orient_matrix_UB_31      0.0050048500
_diffrn_orient_matrix_UB_32      0.1696382500
_diffrn_orient_matrix_UB_33      -0.0023672500
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18816
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.884
_diffrn_reflns_theta_min         2.990
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4015
_reflns_number_total             5534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05210a2.cif
_cod_data_source_block           f678
_cod_depositor_comments          'Adding full bibliography for 7132423.cif.'
_cod_database_code               7132423
_shelx_shelxl_version_number     2018/3
_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.
;
_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:
 C8(H8), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C20(H20), C21(H21), C22(H22), C25(H25),
 C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2023-04-23
_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 2.195
_oxdiff_exptl_absorpt_empirical_full_min 0.361
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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 0.76198(3) 0.57791(9) 0.93409(3) 0.0607(2) Uani 1 1 d . . . . .
Br2 Br 0.27519(3) 0.52232(5) 0.80649(2) 0.03050(14) Uani 1 1 d . . . . .
S1 S 0.39693(6) 0.66819(12) 0.54035(4) 0.0271(2) Uani 1 1 d . . . . .
O1 O 0.43318(16) 0.5031(3) 0.79886(12) 0.0265(7) Uani 1 1 d . . . . .
O2 O 0.50575(19) 0.9745(3) 0.78828(12) 0.0341(8) Uani 1 1 d . . . . .
O3 O 0.34401(19) 0.6602(4) 0.49752(12) 0.0375(8) Uani 1 1 d . . . . .
O4 O 0.44103(19) 0.7934(3) 0.55095(12) 0.0316(8) Uani 1 1 d . . . . .
N1 N 0.48488(19) 0.7311(4) 0.80270(13) 0.0224(7) Uani 1 1 d . . . . .
N2 N 0.27436(19) 0.5728(4) 0.64261(13) 0.0232(8) Uani 1 1 d . . . . .
N3 N 0.3598(2) 0.6604(4) 0.57969(13) 0.0257(8) Uani 1 1 d . . . . .
C1 C 0.5495(2) 0.6973(4) 0.83451(15) 0.0214(9) Uani 1 1 d . . . . .
C2 C 0.6073(2) 0.7397(5) 0.82472(17) 0.0278(10) Uani 1 1 d . . . . .
H2 H 0.603432 0.792895 0.797774 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6709(3) 0.7034(5) 0.85482(18) 0.0309(10) Uani 1 1 d . . . . .
H3 H 0.710792 0.730191 0.848375 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6750(3) 0.6287(5) 0.89374(19) 0.0318(11) Uani 1 1 d . . . . .
C5 C 0.6179(3) 0.5840(5) 0.90414(17) 0.0291(10) Uani 1 1 d . . . . .
H5 H 0.622118 0.530454 0.931075 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5546(2) 0.6201(5) 0.87394(15) 0.0244(9) Uani 1 1 d . . . . .
H6 H 0.514812 0.592010 0.880306 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4700(2) 0.8667(4) 0.77915(16) 0.0247(9) Uani 1 1 d . . . . .
C8 C 0.4064(2) 0.8450(4) 0.74006(15) 0.0217(9) Uani 1 1 d . . . . .
H8 H 0.377461 0.935664 0.733924 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4312(2) 0.6306(4) 0.78742(15) 0.0211(9) Uani 1 1 d . . . . .
C10 C 0.3717(2) 0.7149(4) 0.75497(16) 0.0215(9) Uani 1 1 d . . . . .
H10 H 0.343958 0.755762 0.772936 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3259(2) 0.6317(4) 0.71624(16) 0.0218(9) Uani 1 1 d . . . . .
C12 C 0.3259(2) 0.6511(4) 0.67256(16) 0.0211(8) Uani 1 1 d . . . . .
C13 C 0.3720(2) 0.7514(5) 0.65797(15) 0.0223(9) Uani 1 1 d . . . . .
H13 H 0.345615 0.839476 0.642441 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4293(2) 0.8038(5) 0.69947(16) 0.0234(9) Uani 1 1 d . . . . .
H14A H 0.451098 0.891254 0.690943 0.028 Uiso 1 1 calc R U . . .
H14B H 0.463805 0.724614 0.708838 0.028 Uiso 1 1 calc R U . . .
C15 C 0.4059(2) 0.6791(5) 0.62625(15) 0.0240(9) Uani 1 1 d . . . . .
H15A H 0.444705 0.740900 0.625647 0.029 Uiso 1 1 calc R U . . .
H15B H 0.423726 0.580991 0.638545 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3090(3) 0.5429(5) 0.57325(17) 0.0311(10) Uani 1 1 d . . . . .
H16A H 0.331388 0.450743 0.587749 0.037 Uiso 1 1 calc R U . . .
H16B H 0.287802 0.523281 0.540511 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2543(2) 0.5862(6) 0.59360(17) 0.0319(10) Uani 1 1 d . . . . .
H17A H 0.240765 0.689922 0.585148 0.038 Uiso 1 1 calc R U . . .
H17B H 0.214082 0.523087 0.579993 0.038 Uiso 1 1 calc R U . . .
C18 C 0.2703(2) 0.5338(4) 0.71320(16) 0.0220(9) Uani 1 1 d . . . . .
C19 C 0.2389(2) 0.4992(4) 0.66688(17) 0.0245(9) Uani 1 1 d . . . . .
C20 C 0.1835(2) 0.4046(5) 0.65168(18) 0.0278(10) Uani 1 1 d . . . . .
H20 H 0.163475 0.382972 0.620409 0.033 Uiso 1 1 calc R U . . .
C21 C 0.1585(2) 0.3431(5) 0.68360(19) 0.0318(11) Uani 1 1 d . . . . .
H21 H 0.121310 0.276680 0.674125 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1868(2) 0.3767(5) 0.72933(19) 0.0300(10) Uani 1 1 d . . . . .
H22 H 0.168576 0.333717 0.750611 0.036 Uiso 1 1 calc R U . . .
C23 C 0.2412(2) 0.4722(5) 0.74403(17) 0.0257(9) Uani 1 1 d . . . . .
C24 C 0.4469(3) 0.5070(5) 0.54544(17) 0.0298(10) Uani 1 1 d . . . . .
C25 C 0.4232(3) 0.3884(6) 0.51700(18) 0.0371(12) Uani 1 1 d . . . . .
H25 H 0.380035 0.393085 0.494377 0.045 Uiso 1 1 calc R U . . .
C26 C 0.4626(3) 0.2621(6) 0.5215(2) 0.0435(14) Uani 1 1 d . . . . .
H26 H 0.446405 0.181767 0.501248 0.052 Uiso 1 1 calc R U . . .
C27 C 0.5254(3) 0.2509(5) 0.55509(19) 0.0362(12) Uani 1 1 d . . . . .
C28 C 0.5103(3) 0.4998(5) 0.5791(2) 0.0354(11) Uani 1 1 d . . . . .
H28 H 0.527041 0.581801 0.598557 0.042 Uiso 1 1 calc R U . . .
C29 C 0.5478(3) 0.3724(6) 0.5837(2) 0.0396(12) Uani 1 1 d . . . . .
H29 H 0.590323 0.366856 0.606949 0.048 Uiso 1 1 calc R U . . .
C30 C 0.5677(4) 0.1130(6) 0.5601(2) 0.0514(16) Uani 1 1 d . . . . .
H30A H 0.593061 0.116095 0.538704 0.077 Uiso 1 1 calc R U . . .
H30B H 0.538180 0.025895 0.553950 0.077 Uiso 1 1 calc R U . . .
H30C H 0.599418 0.107239 0.591080 0.077 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O3 S1 N3 106.6(2) . . ?
O3 S1 C24 107.2(2) . . ?
O4 S1 O3 120.0(2) . . ?
O4 S1 N3 106.5(2) . . ?
O4 S1 C24 108.3(2) . . ?
N3 S1 C24 107.7(2) . . ?
C7 N1 C1 123.2(4) . . ?
C9 N1 C1 124.8(3) . . ?
C9 N1 C7 111.6(4) . . ?
C12 N2 C17 124.7(4) . . ?
C12 N2 C19 108.3(4) . . ?
C19 N2 C17 126.2(4) . . ?
C15 N3 S1 114.5(3) . . ?
C16 N3 S1 114.9(3) . . ?
C16 N3 C15 115.5(4) . . ?
C2 C1 N1 118.7(4) . . ?
C6 C1 N1 120.5(4) . . ?
C6 C1 C2 120.7(4) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Br1 118.7(4) . . ?
C3 C4 C5 122.5(5) . . ?
C5 C4 Br1 118.8(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(5) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O2 C7 N1 124.4(5) . . ?
O2 C7 C8 128.1(4) . . ?
N1 C7 C8 107.3(4) . . ?
C7 C8 H8 111.8 . . ?
C7 C8 C10 103.6(4) . . ?
C7 C8 C14 105.8(4) . . ?
C10 C8 H8 111.8 . . ?
C10 C8 C14 111.7(3) . . ?
C14 C8 H8 111.8 . . ?
O1 C9 N1 124.9(4) . . ?
O1 C9 C10 128.1(4) . . ?
N1 C9 C10 106.9(3) . . ?
C8 C10 H10 107.8 . . ?
C9 C10 C8 102.8(3) . . ?
C9 C10 H10 107.8 . . ?
C11 C10 C8 112.7(4) . . ?
C11 C10 C9 117.4(3) . . ?
C11 C10 H10 107.8 . . ?
C12 C11 C10 122.5(4) . . ?
C12 C11 C18 105.8(4) . . ?
C18 C11 C10 131.3(4) . . ?
N2 C12 C11 111.0(4) . . ?
N2 C12 C13 123.0(4) . . ?
C11 C12 C13 125.9(4) . . ?
C12 C13 H13 108.8 . . ?
C12 C13 C14 109.6(4) . . ?
C12 C13 C15 114.5(4) . . ?
C14 C13 H13 108.8 . . ?
C14 C13 C15 106.3(4) . . ?
C15 C13 H13 108.8 . . ?
C8 C14 H14A 108.8 . . ?
C8 C14 H14B 108.8 . . ?
C13 C14 C8 114.0(4) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N3 C15 C13 113.3(4) . . ?
N3 C15 H15A 108.9 . . ?
N3 C15 H15B 108.9 . . ?
C13 C15 H15A 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
N3 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
N3 C16 C17 111.3(4) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
N2 C17 C16 114.7(4) . . ?
N2 C17 H17A 108.6 . . ?
N2 C17 H17B 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C11 107.4(4) . . ?
C23 C18 C11 135.7(5) . . ?
C23 C18 C19 116.8(4) . . ?
N2 C19 C18 107.4(4) . . ?
N2 C19 C20 129.7(5) . . ?
C20 C19 C18 122.8(4) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.8(5) . . ?
C21 C20 H20 121.1 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(5) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.5(5) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 Br2 120.4(4) . . ?
C22 C23 Br2 118.9(4) . . ?
C22 C23 C18 120.7(5) . . ?
C25 C24 S1 120.3(4) . . ?
C25 C24 C28 120.2(5) . . ?
C28 C24 S1 119.5(4) . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.9(6) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.2(5) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C29 117.6(5) . . ?
C26 C27 C30 121.1(5) . . ?
C29 C27 C30 121.3(6) . . ?
C24 C28 H28 120.5 . . ?
C29 C28 C24 119.0(5) . . ?
C29 C28 H28 120.5 . . ?
C27 C29 H29 119.0 . . ?
C28 C29 C27 122.1(6) . . ?
C28 C29 H29 119.0 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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 C4 1.901(5) . ?
Br2 C23 1.903(5) . ?
S1 O3 1.435(4) . ?
S1 O4 1.428(4) . ?
S1 N3 1.655(4) . ?
S1 C24 1.769(5) . ?
O1 C9 1.203(5) . ?
O2 C7 1.203(6) . ?
N1 C1 1.427(6) . ?
N1 C7 1.411(6) . ?
N1 C9 1.402(6) . ?
N2 C12 1.372(6) . ?
N2 C17 1.456(6) . ?
N2 C19 1.390(6) . ?
N3 C15 1.471(6) . ?
N3 C16 1.469(6) . ?
C1 C2 1.391(6) . ?
C1 C6 1.390(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(8) . ?
C4 C5 1.394(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.498(7) . ?
C8 H8 1.0000 . ?
C8 C10 1.530(6) . ?
C8 C14 1.539(6) . ?
C9 C10 1.528(6) . ?
C10 H10 1.0000 . ?
C10 C11 1.482(6) . ?
C11 C12 1.376(6) . ?
C11 C18 1.439(6) . ?
C12 C13 1.497(6) . ?
C13 H13 1.0000 . ?
C13 C14 1.528(6) . ?
C13 C15 1.538(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.528(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.417(7) . ?
C18 C23 1.410(6) . ?
C19 C20 1.393(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(7) . ?
C24 C25 1.378(7) . ?
C24 C28 1.400(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.394(9) . ?
C27 C29 1.397(8) . ?
C27 C30 1.506(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.374(7) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
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 C4 C5 C6 -179.1(3) . . . . ?
S1 N3 C15 C13 149.7(3) . . . . ?
S1 N3 C16 C17 -151.1(3) . . . . ?
S1 C24 C25 C26 -179.5(4) . . . . ?
S1 C24 C28 C29 178.1(4) . . . . ?
O1 C9 C10 C8 -158.7(4) . . . . ?
O1 C9 C10 C11 -34.4(6) . . . . ?
O2 C7 C8 C10 -160.9(5) . . . . ?
O2 C7 C8 C14 81.5(6) . . . . ?
O3 S1 N3 C15 -175.4(3) . . . . ?
O3 S1 N3 C16 47.4(4) . . . . ?
O3 S1 C24 C25 -14.9(5) . . . . ?
O3 S1 C24 C28 166.3(4) . . . . ?
O4 S1 N3 C15 -46.1(4) . . . . ?
O4 S1 N3 C16 176.6(3) . . . . ?
O4 S1 C24 C25 -145.7(4) . . . . ?
O4 S1 C24 C28 35.4(5) . . . . ?
N1 C1 C2 C3 -178.0(4) . . . . ?
N1 C1 C6 C5 178.2(4) . . . . ?
N1 C7 C8 C10 23.7(4) . . . . ?
N1 C7 C8 C14 -94.0(4) . . . . ?
N1 C9 C10 C8 22.1(4) . . . . ?
N1 C9 C10 C11 146.3(4) . . . . ?
N2 C12 C13 C14 -172.1(4) . . . . ?
N2 C12 C13 C15 -52.8(5) . . . . ?
N2 C19 C20 C21 178.7(4) . . . . ?
N3 S1 C24 C25 99.5(4) . . . . ?
N3 S1 C24 C28 -79.4(5) . . . . ?
N3 C16 C17 N2 -77.4(5) . . . . ?
C1 N1 C7 O2 -12.1(7) . . . . ?
C1 N1 C7 C8 163.6(4) . . . . ?
C1 N1 C9 O1 -0.8(7) . . . . ?
C1 N1 C9 C10 178.4(4) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C2 C3 C4 Br1 179.3(3) . . . . ?
C2 C3 C4 C5 1.5(7) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C7 N1 C1 C2 -40.6(6) . . . . ?
C7 N1 C1 C6 141.0(4) . . . . ?
C7 N1 C9 O1 172.8(4) . . . . ?
C7 N1 C9 C10 -7.9(5) . . . . ?
C7 C8 C10 C9 -27.2(4) . . . . ?
C7 C8 C10 C11 -154.5(3) . . . . ?
C7 C8 C14 C13 170.2(3) . . . . ?
C8 C10 C11 C12 12.6(6) . . . . ?
C8 C10 C11 C18 -159.6(4) . . . . ?
C9 N1 C1 C2 132.3(4) . . . . ?
C9 N1 C1 C6 -46.0(6) . . . . ?
C9 N1 C7 O2 174.1(4) . . . . ?
C9 N1 C7 C8 -10.2(5) . . . . ?
C9 C10 C11 C12 -106.6(5) . . . . ?
C9 C10 C11 C18 81.3(6) . . . . ?
C10 C8 C14 C13 58.1(5) . . . . ?
C10 C11 C12 N2 -173.8(4) . . . . ?
C10 C11 C12 C13 2.2(7) . . . . ?
C10 C11 C18 C19 172.9(4) . . . . ?
C10 C11 C18 C23 -5.3(8) . . . . ?
C11 C12 C13 C14 12.4(6) . . . . ?
C11 C12 C13 C15 131.6(4) . . . . ?
C11 C18 C19 N2 0.2(4) . . . . ?
C11 C18 C19 C20 179.1(4) . . . . ?
C11 C18 C23 Br2 2.5(7) . . . . ?
C11 C18 C23 C22 -178.8(4) . . . . ?
C12 N2 C17 C16 62.1(6) . . . . ?
C12 N2 C19 C18 -0.2(5) . . . . ?
C12 N2 C19 C20 -178.9(4) . . . . ?
C12 C11 C18 C19 -0.2(4) . . . . ?
C12 C11 C18 C23 -178.4(5) . . . . ?
C12 C13 C14 C8 -41.7(5) . . . . ?
C12 C13 C15 N3 75.3(5) . . . . ?
C14 C8 C10 C9 86.3(4) . . . . ?
C14 C8 C10 C11 -41.0(5) . . . . ?
C14 C13 C15 N3 -163.6(3) . . . . ?
C15 N3 C16 C17 72.1(5) . . . . ?
C15 C13 C14 C8 -165.9(3) . . . . ?
C16 N3 C15 C13 -73.3(5) . . . . ?
C17 N2 C12 C11 170.7(4) . . . . ?
C17 N2 C12 C13 -5.5(6) . . . . ?
C17 N2 C19 C18 -170.6(4) . . . . ?
C17 N2 C19 C20 10.7(7) . . . . ?
C18 C11 C12 N2 0.1(5) . . . . ?
C18 C11 C12 C13 176.1(4) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 N2 C12 C11 0.0(5) . . . . ?
C19 N2 C12 C13 -176.1(4) . . . . ?
C19 N2 C17 C16 -128.9(4) . . . . ?
C19 C18 C23 Br2 -175.6(3) . . . . ?
C19 C18 C23 C22 3.2(6) . . . . ?
C19 C20 C21 C22 1.3(7) . . . . ?
C20 C21 C22 C23 -0.5(7) . . . . ?
C21 C22 C23 Br2 176.9(3) . . . . ?
C21 C22 C23 C18 -1.9(7) . . . . ?
C23 C18 C19 N2 178.8(4) . . . . ?
C23 C18 C19 C20 -2.4(6) . . . . ?
C24 S1 N3 C15 69.9(4) . . . . ?
C24 S1 N3 C16 -67.4(4) . . . . ?
C24 C25 C26 C27 1.6(9) . . . . ?
C24 C28 C29 C27 1.4(8) . . . . ?
C25 C24 C28 C29 -0.8(8) . . . . ?
C25 C26 C27 C29 -1.0(8) . . . . ?
C25 C26 C27 C30 179.4(5) . . . . ?
C26 C27 C29 C28 -0.5(8) . . . . ?
C28 C24 C25 C26 -0.7(8) . . . . ?
C30 C27 C29 C28 179.1(5) . . . . ?
