#------------------------------------------------------------------------------
#$Date: 2022-01-26 00:50:45 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129611.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_7129611
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 O2 S2'
_chemical_formula_weight         309.23
_chemical_name_common            dioxTN-Br
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-08 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.813(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7355(3)
_cell_length_b                   9.6941(2)
_cell_length_c                   8.6079(3)
_cell_measurement_reflns_used    6897
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.8430
_cell_measurement_theta_min      2.6020
_cell_volume                     585.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Rigaku Pilatus 200K
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7902
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79967
_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            white
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       platlet
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0215
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2532
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06996a2.cif
_cod_data_source_block           18
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129611
_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.
;
_shelx_estimated_absorpt_t_min   0.514
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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 0.38153(5) 0.24817(3) -0.02032(4) 0.03896(12) Uani 1 1 d . . . . .
S002 S 0.93680(10) 0.61987(8) 0.48041(10) 0.02549(17) Uani 1 1 d . . . . .
S003 S 0.73106(11) 0.41768(8) 0.20806(10) 0.02559(17) Uani 1 1 d . . . . .
O004 O 0.8754(3) 0.7546(3) 0.5037(3) 0.0388(6) Uani 1 1 d . . . . .
O005 O 1.0466(3) 0.6069(3) 0.3816(3) 0.0386(6) Uani 1 1 d . . . . .
C006 C 0.5685(4) 0.5115(3) 0.3959(4) 0.0221(6) Uani 1 1 d . . . . .
C007 C 0.5030(4) 0.3686(3) 0.1633(4) 0.0254(6) Uani 1 1 d . . . . .
C008 C 0.4334(4) 0.4234(3) 0.2712(4) 0.0252(6) Uani 1 1 d . . . . .
H008 H 0.309700 0.405039 0.264254 0.030 Uiso 1 1 calc R U . . .
C009 C 0.5578(5) 0.4639(4) 0.6772(4) 0.0308(7) Uani 1 1 d . . . . .
H00A H 0.542211 0.509685 0.773380 0.037 Uiso 1 1 calc R U . . .
H00B H 0.452847 0.396355 0.626799 0.037 Uiso 1 1 calc R U . . .
C00A C 0.7459(4) 0.3848(4) 0.7498(4) 0.0314(7) Uani 1 1 d . . . . .
H00C H 0.776521 0.358187 0.653182 0.038 Uiso 1 1 calc R U . . .
H00D H 0.726478 0.298517 0.802018 0.038 Uiso 1 1 calc R U . . .
C00B C 0.5350(4) 0.5736(3) 0.5409(4) 0.0271(6) Uani 1 1 d . . . . .
H00E H 0.405010 0.612946 0.496456 0.033 Uiso 1 1 calc R U . . .
H00F H 0.627089 0.649300 0.593470 0.033 Uiso 1 1 calc R U . . .
C00C C 0.7340(4) 0.5184(3) 0.3744(4) 0.0207(6) Uani 1 1 d . . . . .
C00D C 1.0055(5) 0.5798(4) 0.8250(4) 0.0308(7) Uani 1 1 d . . . . .
H00G H 0.909853 0.654672 0.783397 0.037 Uiso 1 1 calc R U . . .
H00H H 1.115926 0.615416 0.925764 0.037 Uiso 1 1 calc R U . . .
C00E C 1.0712(4) 0.5463(3) 0.6845(4) 0.0238(6) Uani 1 1 d . . . . .
H00I H 1.069998 0.444857 0.671233 0.029 Uiso 1 1 calc R U . . .
H00J H 1.204947 0.577204 0.723896 0.029 Uiso 1 1 calc R U . . .
C00F C 0.9189(5) 0.4591(4) 0.8829(4) 0.0383(8) Uani 1 1 d . . . . .
H00K H 1.020411 0.389531 0.936714 0.046 Uiso 1 1 calc R U . . .
H00L H 0.882856 0.493737 0.973457 0.046 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 0.0033 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 O005 118.39(16) . . ?
O004 S002 C00C 107.94(14) . . ?
O005 S002 C00C 105.40(15) . . ?
O004 S002 C00E 108.58(15) . . ?
O005 S002 C00E 107.76(14) . . ?
C00C S002 C00E 108.40(14) . . ?
C007 S003 C00C 89.85(14) . . ?
C00C C006 C008 111.1(3) . . ?
C00C C006 C00B 126.1(3) . . ?
C008 C006 C00B 122.5(3) . . ?
C008 C007 S003 113.9(2) . . ?
C008 C007 Br01 128.1(2) . . ?
S003 C007 Br01 118.00(17) . . ?
C007 C008 C006 111.8(3) . . ?
C00A C009 C00B 116.3(2) . . ?
C009 C00A C00F 117.0(3) . . ?
C006 C00B C009 110.6(3) . . ?
C006 C00C S003 113.4(2) . . ?
C006 C00C S002 129.9(2) . . ?
S003 C00C S002 116.60(17) . . ?
C00E C00D C00F 115.5(3) . . ?
C00D C00E S002 116.5(2) . . ?
C00A C00F C00D 118.7(3) . . ?
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 C007 1.871(3) . ?
S002 O004 1.432(3) . ?
S002 O005 1.438(2) . ?
S002 C00C 1.749(3) . ?
S002 C00E 1.773(3) . ?
S003 C007 1.708(3) . ?
S003 C00C 1.726(3) . ?
C006 C00C 1.370(4) . ?
C006 C008 1.426(4) . ?
C006 C00B 1.503(4) . ?
C007 C008 1.361(5) . ?
C009 C00A 1.528(5) . ?
C009 C00B 1.538(5) . ?
C00A C00F 1.528(5) . ?
C00D C00E 1.530(4) . ?
C00D C00F 1.532(5) . ?
