#------------------------------------------------------------------------------
#$Date: 2022-01-26 00:50:45 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129618.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_7129618
loop_
_publ_author_name
'Hayakawa, Masahiro'
'Horike, Satoshi'
'Hijikata, Yuh'
'Yasui, Kosuke'
'Yamaguchi, Shigehiro'
'Fukazawa, Aiko'
_publ_section_title
;
 Late-Stage Modification of π-Electron Systems Based on Asymmetric
 Oxidation of a Medium-Sized Sulfur-Containing Ring
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06996A
_journal_year                    2022
_chemical_formula_sum            'C10 H13 Br O S2'
_chemical_formula_weight         293.23
_chemical_name_common            (R)-oxTN-Br
_chemical_name_systematic
'(R)-2-bromo-4,5,6,7,8,9-hexahydrothieno[2,3-b]thionine S-oxide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.66070(10)
_cell_length_b                   9.6197(2)
_cell_length_c                   15.2085(3)
_cell_measurement_reflns_used    14188
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.8330
_cell_measurement_theta_min      2.5160
_cell_volume                     1120.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Rigaku Saturn70 (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15102
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.505
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    4.004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.214
_refine_ls_R_factor_all          0.0152
_refine_ls_R_factor_gt           0.0146
_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)+(0.0252P)²+0.1126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0449
_refine_ls_wR_factor_ref         0.0452
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2520
_reflns_number_total             2561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06996a2.cif
_cod_data_source_block           R-2
_cod_database_code               7129618
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br01 Br 0.53945(3) 0.31248(2) 0.51594(2) 0.02097(8) Uani 1 1 d . . . . .
S002 S 0.22917(7) 0.57009(6) 0.19662(4) 0.01473(12) Uani 1 1 d . . . . .
S003 S 0.29537(8) 0.45255(6) 0.37853(4) 0.01675(13) Uani 1 1 d . . . . .
O004 O 0.0834(2) 0.64640(18) 0.24166(13) 0.0244(4) Uani 1 1 d . . . . .
C005 C 0.4956(3) 0.4083(2) 0.05193(16) 0.0166(5) Uani 1 1 d . . . . .
H00A H 0.432689 0.497310 0.060088 0.020 Uiso 1 1 calc R U . . .
H00B H 0.539441 0.406571 -0.009288 0.020 Uiso 1 1 calc R U . . .
C006 C 0.5491(3) 0.4853(2) 0.26670(15) 0.0140(4) Uani 1 1 d . . . . .
C007 C 0.2658(3) 0.2826(2) 0.15031(17) 0.0170(5) Uani 1 1 d . . . . .
H00C H 0.200782 0.193751 0.152436 0.020 Uiso 1 1 calc R U . . .
H00D H 0.352621 0.280870 0.198514 0.020 Uiso 1 1 calc R U . . .
C008 C 0.6546(3) 0.5202(3) 0.18629(16) 0.0161(5) Uani 1 1 d . . . . .
H00E H 0.776860 0.537320 0.204462 0.019 Uiso 1 1 calc R U . . .
H00F H 0.609090 0.607711 0.160793 0.019 Uiso 1 1 calc R U . . .
C009 C 0.3742(3) 0.5103(2) 0.27827(16) 0.0140(4) Uani 1 1 d . . . . .
C00A C 0.3642(3) 0.2896(2) 0.06278(16) 0.0186(5) Uani 1 1 d . . . . .
H00G H 0.277123 0.296869 0.014898 0.022 Uiso 1 1 calc R U . . .
H00H H 0.427177 0.200650 0.054629 0.022 Uiso 1 1 calc R U . . .
C00B C 0.6539(3) 0.4074(2) 0.11424(17) 0.0167(5) Uani 1 1 d . . . . .
H00I H 0.761017 0.418037 0.078468 0.020 Uiso 1 1 calc R U . . .
H00J H 0.659711 0.315278 0.143140 0.020 Uiso 1 1 calc R U . . .
C00C C 0.6214(3) 0.4172(2) 0.34188(16) 0.0160(5) Uani 1 1 d . . . . .
H00K H 0.740794 0.391532 0.346881 0.019 Uiso 1 1 calc R U . . .
C00D C 0.1375(3) 0.4010(2) 0.16805(17) 0.0172(5) Uani 1 1 d . . . . .
H00L H 0.059408 0.371750 0.216507 0.021 Uiso 1 1 calc R U . . .
H00M H 0.064087 0.412998 0.115023 0.021 Uiso 1 1 calc R U . . .
C00E C 0.5008(3) 0.3933(2) 0.40510(16) 0.0161(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables 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'
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'
Br Br -0.2901 2.4595 '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
O004 S002 C009 107.86(11) . . ?
O004 S002 C00D 104.96(11) . . ?
C009 S002 C00D 96.87(11) . . ?
C00E S003 C009 89.68(12) . . ?
C00A C005 C00B 116.6(2) . . ?
C009 C006 C00C 110.9(2) . . ?
C009 C006 C008 126.2(2) . . ?
C00C C006 C008 122.9(2) . . ?
C00D C007 C00A 115.9(2) . . ?
C006 C008 C00B 114.7(2) . . ?
C006 C009 S003 113.39(19) . . ?
C006 C009 S002 125.6(2) . . ?
S003 C009 S002 120.36(14) . . ?
C007 C00A C005 116.7(2) . . ?
C005 C00B C008 115.9(2) . . ?
C00E C00C C006 112.4(2) . . ?
C007 C00D S002 117.31(17) . . ?
C00C C00E S003 113.66(18) . . ?
C00C C00E Br01 126.85(18) . . ?
S003 C00E Br01 119.43(14) . . ?
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 C00E 1.880(2) . ?
S002 O004 1.5018(18) . ?
S002 C009 1.762(2) . ?
S002 C00D 1.824(2) . ?
S003 C00E 1.722(2) . ?
S003 C009 1.732(2) . ?
C005 C00A 1.531(3) . ?
C005 C00B 1.539(3) . ?
C006 C009 1.373(3) . ?
C006 C00C 1.430(3) . ?
C006 C008 1.504(3) . ?
C007 C00D 1.528(3) . ?
C007 C00A 1.531(3) . ?
C008 C00B 1.543(3) . ?
C00C C00E 1.353(3) . ?
