#------------------------------------------------------------------------------
#$Date: 2022-08-02 23:57:45 +0200 (Tue 02 de Aug de 2022) $
#$Revision: 277043 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/04/7130465.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_7130465
loop_
_publ_author_name
'Yu, Ke-Yin'
'Ge, Xiao-Min'
'Fan, Yi-Jun'
'Liu, Xiao-Tao'
'Yang, Xue'
'Yang, Yu-Han'
'Zhao, Xian-He'
'An, Xian-Tao'
'Fan, Chun-An'
_publ_section_title
;
 Iron(III)-catalyzed tandem annulation of indolyl-substituted
 p-quinone methides with ynamides for the synthesis of
 cyclopenta[b]indoles.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8710
_journal_page_last               8713
_journal_paper_doi               10.1039/d2cc03252j
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C46 H47 Br N2 O4 S'
_chemical_formula_sum            'C46 H47 Br N2 O4 S'
_chemical_formula_weight         803.82
_chemical_melting_point          478.6(5)
_chemical_name_systematic        'Compound 3ia'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-15 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.55960(10)
_cell_length_b                   12.86910(10)
_cell_length_c                   30.3703(3)
_cell_measurement_reflns_used    18218
_cell_measurement_temperature    303.78(10)
_cell_measurement_theta_max      76.2650
_cell_measurement_theta_min      2.9020
_cell_volume                     4103.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.78(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 176.00   0.50    0.05    --  104.25  45.00-150.00  168
  2  ω    106.00 176.00   0.50    0.05    --  104.25 104.00-120.00  140
  3  ω    -28.00  27.00   0.50    0.05    --   46.32 -19.00  60.00  110
  4  ω     35.00  61.00   0.50    0.05    --   46.32-104.00 137.00   52
  5  ω     75.00 105.00   0.50    0.05    --  104.25-104.00 137.00   60
  6  ω     34.00  83.00   0.50    0.05    --  104.25 -94.00-180.00   98
  7  ω     39.00  66.00   0.50    0.05    --  104.25 -61.00 -60.00   54
  8  ω     34.00  66.00   0.50    0.05    --  104.25 -61.00 -30.00   64
  9  ω     35.00  60.00   0.50    0.05    --  104.25 -61.00   0.00   50
 10  ω     35.00  71.00   0.50    0.05    --  104.25 -61.00  30.00   72
 11  ω     34.00  60.00   0.50    0.05    --  104.25 -61.00 120.00   52
 12  ω     35.00  60.00   0.50    0.05    --  104.25 -61.00 150.00   50
 13  ω   -104.00 -29.00   0.50    0.05    -- -102.00  77.00-120.00  150
 14  ω    -69.00 -30.00   0.50    0.05    -- -102.00  61.00  90.00   78
 15  ω    -66.00 -30.00   0.50    0.05    -- -102.00  61.00  60.00   72
 16  ω    -57.00 -29.00   0.50    0.05    -- -102.00  61.00  30.00   56
 17  ω    -58.00 -32.00   0.50    0.05    -- -102.00  61.00   0.00   52
 18  ω    -57.00 -32.00   0.50    0.05    -- -102.00  61.00 -30.00   50
 19  ω    -40.00  18.00   0.50    0.05    --  -46.32  37.00   0.00  116
 20  ω   -118.00 -76.00   0.50    0.05    --  -46.32-125.00 -60.00   84
 21  ω   -118.00 -84.00   0.50    0.05    --  -46.32-125.00 -90.00   68
 22  ω   -116.00 -90.00   0.50    0.05    --  -46.32-125.00-180.00   52
 23  ω    -81.00   1.00   0.50    0.05    --  -46.32 104.00-120.00  164
 24  ω   -105.00 -52.00   0.50    0.05    -- -102.00 104.00-120.00  106
 25  ω   -155.00 -86.00   0.50    0.05    -- -102.00-104.00 137.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137903000
_diffrn_orient_matrix_UB_12      -0.1140250000
_diffrn_orient_matrix_UB_13      -0.0152422000
_diffrn_orient_matrix_UB_21      0.1442097000
_diffrn_orient_matrix_UB_22      -0.0162304000
_diffrn_orient_matrix_UB_23      0.0117463000
_diffrn_orient_matrix_UB_31      -0.0232784000
_diffrn_orient_matrix_UB_32      -0.0327051000
_diffrn_orient_matrix_UB_33      0.0472514000
_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  0.0556
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            29600
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.451
_diffrn_reflns_theta_min         2.927
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8255
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0470
_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)+(0.0629P)²+1.3607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6899
_reflns_number_total             8255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3ia
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '478.15-479.15' was changed
to '478.6(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130465
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 H26C-H4
 2.1 with sigma of 0.01
 H4-H25A
 2.1 with sigma of 0.01
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C14(H14), C18(H18), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C41(H41), C42(H42),
  C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C39(H39A,
 H39B,H39C), C46(H46A,H46B,H46C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 4.755
_oxdiff_exptl_absorpt_empirical_full_min 0.385
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br01 Br 1.01671(3) 0.68596(3) 0.46232(2) 0.08124(14) Uani 1 1 d . . . . .
S1 S 0.54192(5) 0.70917(4) 0.65095(2) 0.04043(13) Uani 1 1 d . . . . .
O1 O 0.52362(16) 0.72614(12) 0.60398(5) 0.0491(4) Uani 1 1 d . . . . .
O2 O 0.62774(17) 0.77373(12) 0.67832(5) 0.0531(4) Uani 1 1 d . . . . .
O3 O 0.57418(19) 0.61891(16) 0.74641(5) 0.0658(5) Uani 1 1 d . . . . .
O4 O 0.5792(2) -0.04788(14) 0.60192(8) 0.0845(7) Uani 1 1 d . . . . .
H4 H 0.523916 -0.083619 0.588259 0.127 Uiso 1 1 calc DR U . . .
N1 N 0.65876(17) 0.44020(13) 0.51809(5) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.59179(16) 0.58738(13) 0.65866(5) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.7338(2) 0.57773(16) 0.56118(7) 0.0410(4) Uani 1 1 d . . . . .
C2 C 0.8092(2) 0.66598(19) 0.57036(8) 0.0529(5) Uani 1 1 d . . . . .
H2 H 0.803286 0.703710 0.596176 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8925(3) 0.6967(2) 0.54085(9) 0.0606(6) Uani 1 1 d . . . . .
H3 H 0.943061 0.755257 0.546662 0.073 Uiso 1 1 calc R U . . .
C4 C 0.9005(2) 0.6394(2) 0.50221(9) 0.0563(6) Uani 1 1 d . . . . .
C5 C 0.8293(2) 0.5530(2) 0.49133(7) 0.0511(5) Uani 1 1 d . . . . .
H5 H 0.837088 0.516068 0.465427 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7441(2) 0.52265(17) 0.52108(7) 0.0417(4) Uani 1 1 d . . . . .
C7 C 0.6384(3) 0.3660(2) 0.48217(7) 0.0555(6) Uani 1 1 d . . . . .
H7A H 0.613739 0.402204 0.454952 0.083 Uiso 1 1 calc R U . . .
H7B H 0.572170 0.318447 0.488016 0.083 Uiso 1 1 calc R U . . .
H7C H 0.715681 0.328213 0.479731 0.083 Uiso 1 1 calc R U . . .
C8 C 0.59816(19) 0.44195(15) 0.55566(6) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.64013(19) 0.52218(15) 0.58250(6) 0.0383(4) Uani 1 1 d . . . . .
C10 C 0.56959(19) 0.51819(14) 0.62141(6) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.48406(18) 0.43938(14) 0.61740(6) 0.0357(4) Uani 1 1 d . . . . .
C12 C 0.49387(19) 0.38149(15) 0.57326(6) 0.0367(4) Uani 1 1 d . . . . .
H12 H 0.414823 0.392388 0.553780 0.044 Uiso 1 1 calc R U . . .
C13 C 0.51587(19) 0.26564(15) 0.57923(6) 0.0371(4) Uani 1 1 d . . . . .
C14 C 0.6294(2) 0.22902(16) 0.60065(7) 0.0410(4) Uani 1 1 d . . . . .
H14 H 0.692657 0.276627 0.610295 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6526(2) 0.12424(17) 0.60831(7) 0.0437(5) Uani 1 1 d . . . . .
C16 C 0.5529(2) 0.05462(16) 0.59403(7) 0.0465(5) Uani 1 1 d . . . . .
C17 C 0.4356(2) 0.08828(16) 0.57259(7) 0.0411(4) Uani 1 1 d . . . . .
C18 C 0.4213(2) 0.19456(15) 0.56522(6) 0.0393(4) Uani 1 1 d . . . . .
H18 H 0.345447 0.218829 0.550343 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7808(2) 0.0852(2) 0.63125(9) 0.0573(6) Uani 1 1 d . . . . .
C20 C 0.8710(3) 0.1756(3) 0.64472(12) 0.0816(10) Uani 1 1 d . . . . .
H20A H 0.885941 0.214847 0.618895 0.122 Uiso 1 1 calc R U . . .
H20B H 0.950405 0.148905 0.658548 0.122 Uiso 1 1 calc R U . . .
H20C H 0.833232 0.219811 0.665175 0.122 Uiso 1 1 calc R U . . .
C21 C 0.7628(3) 0.0253(3) 0.67371(11) 0.0835(10) Uani 1 1 d . . . . .
H21A H 0.727326 0.070676 0.694258 0.125 Uiso 1 1 calc R U . . .
H21B H 0.843705 -0.000305 0.686716 0.125 Uiso 1 1 calc R U . . .
H21C H 0.706077 -0.032135 0.666769 0.125 Uiso 1 1 calc R U . . .
C22 C 0.8476(4) 0.0159(4) 0.59917(15) 0.1042(13) Uani 1 1 d . . . . .
H22A H 0.795576 -0.043801 0.591166 0.156 Uiso 1 1 calc R U . . .
H22B H 0.928635 -0.006418 0.613400 0.156 Uiso 1 1 calc R U . . .
H22C H 0.860091 0.054751 0.573006 0.156 Uiso 1 1 calc R U . . .
C23 C 0.3243(2) 0.01278(18) 0.55896(8) 0.0516(5) Uani 1 1 d . . . . .
C24 C 0.2096(3) 0.0695(2) 0.53521(13) 0.0827(10) Uani 1 1 d . . . . .
H24A H 0.181276 0.121969 0.554366 0.124 Uiso 1 1 calc R U . . .
H24B H 0.142007 0.020751 0.527587 0.124 Uiso 1 1 calc R U . . .
H24C H 0.233533 0.101415 0.508755 0.124 Uiso 1 1 calc R U . . .
C25 C 0.2814(3) -0.0381(3) 0.60077(11) 0.0901(11) Uani 1 1 d . . . . .
H25A H 0.352271 -0.073403 0.616652 0.135 Uiso 1 1 calc DR U . . .
H25B H 0.214573 -0.087011 0.592388 0.135 Uiso 1 1 calc R U . . .
H25C H 0.250693 0.014560 0.619354 0.135 Uiso 1 1 calc R U . . .
C26 C 0.3607(3) -0.0710(2) 0.52674(11) 0.0805(9) Uani 1 1 d . . . . .
H26A H 0.435037 -0.049247 0.513575 0.121 Uiso 1 1 calc R U . . .
H26B H 0.291477 -0.081231 0.503956 0.121 Uiso 1 1 calc R U . . .
H26C H 0.378360 -0.134913 0.542488 0.121 Uiso 1 1 calc DR U . . .
C27 C 0.3918(2) 0.40695(15) 0.64769(7) 0.0392(4) Uani 1 1 d . . . . .
C28 C 0.2755(2) 0.3648(2) 0.63118(8) 0.0550(6) Uani 1 1 d . . . . .
H28 H 0.256177 0.357167 0.600752 0.066 Uiso 1 1 calc R U . . .
C29 C 0.1877(3) 0.3339(3) 0.65933(11) 0.0745(8) Uani 1 1 d . . . . .
H29 H 0.110310 0.305250 0.647749 0.089 Uiso 1 1 calc R U . . .
C30 C 0.2147(3) 0.3454(3) 0.70432(10) 0.0742(8) Uani 1 1 d . . . . .
H30 H 0.155811 0.324387 0.723182 0.089 Uiso 1 1 calc R U . . .
C31 C 0.3282(3) 0.3877(2) 0.72137(9) 0.0660(7) Uani 1 1 d . . . . .
H31 H 0.345664 0.396334 0.751823 0.079 Uiso 1 1 calc R U . . .
C32 C 0.4177(2) 0.41778(19) 0.69356(7) 0.0520(5) Uani 1 1 d . . . . .
H32 H 0.495236 0.445333 0.705521 0.062 Uiso 1 1 calc R U . . .
C33 C 0.6967(2) 0.56457(17) 0.69169(7) 0.0486(5) Uani 1 1 d . . . . .
C34 C 0.8090(2) 0.5219(2) 0.67819(10) 0.0637(7) Uani 1 1 d . . . . .
H34 H 0.816337 0.510573 0.648334 0.076 Uiso 1 1 calc R U . . .
C35 C 0.9090(3) 0.4970(3) 0.71019(13) 0.0871(10) Uani 1 1 d . . . . .
H35 H 0.982901 0.466581 0.702040 0.104 Uiso 1 1 calc R U . . .
C36 C 0.8971(4) 0.5179(3) 0.75403(13) 0.0926(11) Uani 1 1 d . . . . .
H36 H 0.965526 0.503576 0.775072 0.111 Uiso 1 1 calc R U . . .
C37 C 0.7889(4) 0.5589(3) 0.76775(10) 0.0805(9) Uani 1 1 d . . . . .
H37 H 0.783653 0.571379 0.797657 0.097 Uiso 1 1 calc R U . . .
C38 C 0.6862(3) 0.58175(19) 0.73645(8) 0.0575(6) Uani 1 1 d . . . . .
C39 C 0.5520(4) 0.6240(3) 0.79215(9) 0.0933(11) Uani 1 1 d . . . . .
H39A H 0.467068 0.648485 0.794354 0.140 Uiso 1 1 calc R U . . .
H39B H 0.612100 0.670899 0.807569 0.140 Uiso 1 1 calc R U . . .
H39C H 0.562143 0.556110 0.805129 0.140 Uiso 1 1 calc R U . . .
C40 C 0.3894(2) 0.71583(17) 0.66914(7) 0.0478(5) Uani 1 1 d . . . . .
C41 C 0.2864(3) 0.6728(2) 0.64356(10) 0.0639(7) Uani 1 1 d . . . . .
H41 H 0.298804 0.635110 0.618244 0.077 Uiso 1 1 calc R U . . .
C42 C 0.1659(3) 0.6856(3) 0.65557(13) 0.0803(9) Uani 1 1 d . . . . .
H42 H 0.097041 0.657166 0.637972 0.096 Uiso 1 1 calc R U . . .
C43 C 0.1446(3) 0.7402(2) 0.69340(13) 0.0808(9) Uani 1 1 d . . . . .
C44 C 0.2492(3) 0.7806(3) 0.71889(11) 0.0778(9) Uani 1 1 d . . . . .
H44 H 0.237146 0.816488 0.744683 0.093 Uiso 1 1 calc R U . . .
C45 C 0.3706(3) 0.7692(2) 0.70729(9) 0.0641(7) Uani 1 1 d . . . . .
H45 H 0.439570 0.797316 0.724986 0.077 Uiso 1 1 calc R U . . .
C46 C 0.0102(4) 0.7582(4) 0.7052(2) 0.1294(19) Uani 1 1 d . . . . .
H46A H -0.030224 0.810987 0.686274 0.194 Uiso 1 1 calc R U . . .
H46B H 0.013446 0.780161 0.735508 0.194 Uiso 1 1 calc R U . . .
H46C H -0.037546 0.694781 0.701278 0.194 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
O1 S1 N2 106.87(8) . . ?
O1 S1 C40 105.93(11) . . ?
O2 S1 O1 119.92(10) . . ?
O2 S1 N2 107.16(9) . . ?
O2 S1 C40 109.50(11) . . ?
N2 S1 C40 106.77(10) . . ?
C38 O3 C39 118.3(2) . . ?
C16 O4 H4 109.5 . . ?
C6 N1 C7 126.58(18) . . ?
C8 N1 C6 106.94(16) . . ?
C8 N1 C7 126.47(19) . . ?
C10 N2 S1 116.78(12) . . ?
C10 N2 C33 117.96(16) . . ?
C33 N2 S1 119.86(14) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C9 136.3(2) . . ?
C6 C1 C9 104.96(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 Br01 117.9(2) . . ?
C5 C4 Br01 118.5(2) . . ?
C5 C4 C3 123.6(2) . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(2) . . ?
C6 C5 H5 121.7 . . ?
N1 C6 C1 109.16(17) . . ?
N1 C6 C5 129.0(2) . . ?
C5 C6 C1 121.8(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C12 136.02(18) . . ?
C9 C8 N1 111.17(18) . . ?
C9 C8 C12 112.72(17) . . ?
C1 C9 C10 145.02(19) . . ?
C8 C9 C1 107.75(17) . . ?
C8 C9 C10 107.21(17) . . ?
N2 C10 C9 123.98(17) . . ?
C11 C10 N2 125.78(17) . . ?
C11 C10 C9 110.22(16) . . ?
C10 C11 C12 109.42(16) . . ?
C10 C11 C27 129.51(18) . . ?
C27 C11 C12 121.07(17) . . ?
C8 C12 C11 100.37(15) . . ?
C8 C12 H12 108.8 . . ?
C8 C12 C13 116.45(17) . . ?
C11 C12 H12 108.8 . . ?
C13 C12 C11 113.18(15) . . ?
C13 C12 H12 108.8 . . ?
C14 C13 C12 120.31(17) . . ?
C14 C13 C18 118.59(18) . . ?
C18 C13 C12 121.04(18) . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.60(19) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C16 116.92(19) . . ?
C14 C15 C19 121.7(2) . . ?
C16 C15 C19 121.4(2) . . ?
O4 C16 C15 115.4(2) . . ?
O4 C16 C17 122.2(2) . . ?
C17 C16 C15 122.48(19) . . ?
C16 C17 C23 122.50(19) . . ?
C18 C17 C16 116.95(19) . . ?
C18 C17 C23 120.51(19) . . ?
C13 C18 C17 122.43(19) . . ?
C13 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C15 C19 C22 110.0(2) . . ?
C20 C19 C15 111.3(2) . . ?
C20 C19 C22 107.1(3) . . ?
C21 C19 C15 111.3(2) . . ?
C21 C19 C20 106.7(2) . . ?
C21 C19 C22 110.3(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C17 111.56(19) . . ?
C24 C23 C25 107.7(3) . . ?
C24 C23 C26 106.0(2) . . ?
C25 C23 C17 109.2(2) . . ?
C26 C23 C17 112.2(2) . . ?
C26 C23 C25 110.1(3) . . ?
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 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C11 120.36(19) . . ?
C28 C27 C32 118.0(2) . . ?
C32 C27 C11 121.59(19) . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.0(2) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(2) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.4(3) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C34 C33 N2 119.0(2) . . ?
C38 C33 N2 120.7(2) . . ?
C38 C33 C34 120.2(2) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 C33 119.1(3) . . ?
C35 C34 H34 120.5 . . ?
C34 C35 H35 120.4 . . ?
C36 C35 C34 119.2(3) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 H36 118.7 . . ?
C37 C36 C35 122.5(3) . . ?
C37 C36 H36 118.7 . . ?
C36 C37 H37 120.4 . . ?
C36 C37 C38 119.3(3) . . ?
C38 C37 H37 120.4 . . ?
O3 C38 C33 116.2(2) . . ?
O3 C38 C37 124.2(3) . . ?
C33 C38 C37 119.6(3) . . ?
O3 C39 H39A 109.5 . . ?
O3 C39 H39B 109.5 . . ?
O3 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 S1 119.69(18) . . ?
C45 C40 S1 120.4(2) . . ?
C45 C40 C41 119.8(2) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 119.9(3) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.3 . . ?
C41 C42 C43 121.3(3) . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C46 120.8(4) . . ?
C44 C43 C42 117.7(3) . . ?
C44 C43 C46 121.5(3) . . ?
C43 C44 H44 119.0 . . ?
C45 C44 C43 121.9(3) . . ?
C45 C44 H44 119.0 . . ?
C40 C45 H45 120.3 . . ?
C44 C45 C40 119.4(3) . . ?
C44 C45 H45 120.3 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
Br01 C4 1.911(2) . ?
S1 O1 1.4356(15) . ?
S1 O2 1.4284(16) . ?
S1 N2 1.6620(17) . ?
S1 C40 1.760(2) . ?
O3 C38 1.341(3) . ?
O3 C39 1.435(3) . ?
O4 H4 0.8200 . ?
O4 C16 1.364(3) . ?
N1 C6 1.388(3) . ?
N1 C7 1.448(3) . ?
N1 C8 1.367(2) . ?
N2 C10 1.439(2) . ?
N2 C33 1.442(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.423(3) . ?
C1 C9 1.431(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 C5 1.363(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.360(3) . ?
C8 C12 1.493(3) . ?
C9 C10 1.464(3) . ?
C10 C11 1.355(3) . ?
C11 C12 1.547(3) . ?
C11 C27 1.470(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.517(3) . ?
C13 C14 1.384(3) . ?
C13 C18 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 C16 1.414(3) . ?
C15 C19 1.539(3) . ?
C16 C17 1.404(3) . ?
C17 C18 1.392(3) . ?
C17 C23 1.547(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.532(4) . ?
C19 C21 1.532(4) . ?
C19 C22 1.546(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.527(4) . ?
C23 C25 1.539(4) . ?
C23 C26 1.532(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.386(3) . ?
C27 C32 1.397(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.374(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.366(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.388(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.407(4) . ?
C33 C38 1.393(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.394(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.377(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.364(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.394(4) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.383(4) . ?
C40 C45 1.380(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.371(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.386(5) . ?
C43 C44 1.380(5) . ?
C43 C46 1.518(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.373(4) . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 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
Br01 C4 C5 C6 -178.98(16) . . . . ?
S1 N2 C10 C9 72.9(2) . . . . ?
S1 N2 C10 C11 -108.7(2) . . . . ?
S1 N2 C33 C34 -117.4(2) . . . . ?
S1 N2 C33 C38 64.3(3) . . . . ?
S1 C40 C41 C42 -174.3(2) . . . . ?
S1 C40 C45 C44 174.7(2) . . . . ?
O1 S1 N2 C10 -18.34(18) . . . . ?
O1 S1 N2 C33 135.21(17) . . . . ?
O1 S1 C40 C41 39.2(2) . . . . ?
O1 S1 C40 C45 -136.7(2) . . . . ?
O2 S1 N2 C10 -148.07(15) . . . . ?
O2 S1 N2 C33 5.48(19) . . . . ?
O2 S1 C40 C41 169.9(2) . . . . ?
O2 S1 C40 C45 -6.1(2) . . . . ?
O4 C16 C17 C18 -178.1(2) . . . . ?
O4 C16 C17 C23 4.0(4) . . . . ?
N1 C8 C9 C1 0.5(2) . . . . ?
N1 C8 C9 C10 179.57(16) . . . . ?
N1 C8 C12 C11 -178.1(2) . . . . ?
N1 C8 C12 C13 59.4(3) . . . . ?
N2 S1 C40 C41 -74.4(2) . . . . ?
N2 S1 C40 C45 109.6(2) . . . . ?
N2 C10 C11 C12 -177.82(17) . . . . ?
N2 C10 C11 C27 2.4(3) . . . . ?
N2 C33 C34 C35 -178.1(3) . . . . ?
N2 C33 C38 O3 0.7(3) . . . . ?
N2 C33 C38 C37 179.9(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C9 C10 N2 -4.9(4) . . . . ?
C1 C9 C10 C11 176.5(3) . . . . ?
C2 C1 C6 N1 -178.3(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C9 C8 178.4(3) . . . . ?
C2 C1 C9 C10 0.0(5) . . . . ?
C2 C3 C4 Br01 179.6(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 N1 178.5(2) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C6 N1 C8 C9 0.4(2) . . . . ?
C6 N1 C8 C12 176.6(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C1 C9 C8 -1.2(2) . . . . ?
C6 C1 C9 C10 -179.6(3) . . . . ?
C7 N1 C6 C1 179.2(2) . . . . ?
C7 N1 C6 C5 -0.6(4) . . . . ?
C7 N1 C8 C9 -180.0(2) . . . . ?
C7 N1 C8 C12 -3.8(4) . . . . ?
C8 N1 C6 C1 -1.1(2) . . . . ?
C8 N1 C6 C5 179.1(2) . . . . ?
C8 C9 C10 N2 176.66(18) . . . . ?
C8 C9 C10 C11 -2.0(2) . . . . ?
C8 C12 C13 C14 48.3(2) . . . . ?
C8 C12 C13 C18 -134.57(19) . . . . ?
C9 C1 C2 C3 179.6(2) . . . . ?
C9 C1 C6 N1 1.4(2) . . . . ?
C9 C1 C6 C5 -178.77(19) . . . . ?
C9 C8 C12 C11 -1.9(2) . . . . ?
C9 C8 C12 C13 -124.43(19) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C9 C10 C11 C27 -178.97(19) . . . . ?
C10 N2 C33 C34 35.8(3) . . . . ?
C10 N2 C33 C38 -142.5(2) . . . . ?
C10 C11 C12 C8 0.6(2) . . . . ?
C10 C11 C12 C13 125.39(18) . . . . ?
C10 C11 C27 C28 147.3(2) . . . . ?
C10 C11 C27 C32 -32.5(3) . . . . ?
C11 C12 C13 C14 -67.3(2) . . . . ?
C11 C12 C13 C18 109.8(2) . . . . ?
C11 C27 C28 C29 180.0(2) . . . . ?
C11 C27 C32 C31 179.2(2) . . . . ?
C12 C8 C9 C1 -176.65(16) . . . . ?
C12 C8 C9 C10 2.4(2) . . . . ?
C12 C11 C27 C28 -32.4(3) . . . . ?
C12 C11 C27 C32 147.8(2) . . . . ?
C12 C13 C14 C15 177.72(19) . . . . ?
C12 C13 C18 C17 -176.02(19) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C13 C14 C15 C19 178.6(2) . . . . ?
C14 C13 C18 C17 1.1(3) . . . . ?
C14 C15 C16 O4 179.7(2) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C14 C15 C19 C20 1.8(3) . . . . ?
C14 C15 C19 C21 120.7(3) . . . . ?
C14 C15 C19 C22 -116.8(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C15 C16 C17 C23 -177.0(2) . . . . ?
C16 C15 C19 C20 -178.3(2) . . . . ?
C16 C15 C19 C21 -59.4(3) . . . . ?
C16 C15 C19 C22 63.2(3) . . . . ?
C16 C17 C18 C13 -1.8(3) . . . . ?
C16 C17 C23 C24 -178.5(2) . . . . ?
C16 C17 C23 C25 62.6(3) . . . . ?
C16 C17 C23 C26 -59.8(3) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C18 C17 C23 C24 3.7(3) . . . . ?
C18 C17 C23 C25 -115.2(3) . . . . ?
C18 C17 C23 C26 122.4(3) . . . . ?
C19 C15 C16 O4 -0.2(3) . . . . ?
C19 C15 C16 C17 -179.3(2) . . . . ?
C23 C17 C18 C13 176.15(19) . . . . ?
C27 C11 C12 C8 -179.65(17) . . . . ?
C27 C11 C12 C13 -54.8(2) . . . . ?
C27 C28 C29 C30 0.5(5) . . . . ?
C28 C27 C32 C31 -0.5(4) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C32 -1.0(5) . . . . ?
C30 C31 C32 C27 1.2(4) . . . . ?
C32 C27 C28 C29 -0.3(4) . . . . ?
C33 N2 C10 C9 -81.2(2) . . . . ?
C33 N2 C10 C11 97.3(2) . . . . ?
C33 C34 C35 C36 -2.2(5) . . . . ?
C34 C33 C38 O3 -177.6(2) . . . . ?
C34 C33 C38 C37 1.6(4) . . . . ?
C34 C35 C36 C37 2.5(6) . . . . ?
C35 C36 C37 C38 -0.7(6) . . . . ?
C36 C37 C38 O3 177.7(3) . . . . ?
C36 C37 C38 C33 -1.4(5) . . . . ?
C38 C33 C34 C35 0.2(4) . . . . ?
C39 O3 C38 C33 171.3(3) . . . . ?
C39 O3 C38 C37 -7.8(4) . . . . ?
C40 S1 N2 C10 94.67(16) . . . . ?
C40 S1 N2 C33 -111.78(18) . . . . ?
C40 C41 C42 C43 -0.8(5) . . . . ?
C41 C40 C45 C44 -1.2(4) . . . . ?
C41 C42 C43 C44 -0.6(5) . . . . ?
C41 C42 C43 C46 177.2(4) . . . . ?
C42 C43 C44 C45 1.1(5) . . . . ?
C43 C44 C45 C40 -0.2(5) . . . . ?
C45 C40 C41 C42 1.7(4) . . . . ?
C46 C43 C44 C45 -176.7(4) . . . . ?
