#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157444.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_7157444
loop_
_publ_author_name
'Jannapu Reddy, Raju'
'Waheed, Md'
'Rama Krishna, Gamidi'
_publ_section_title
;
 Phenylboronic acid-catalyzed tandem construction of S-S and C-S bonds: a
 new method for the synthesis of benzyl disulfanylsulfone derivatives from
 S-benzyl thiosulfonates.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3243
_journal_page_last               3248
_journal_paper_doi               10.1039/d0ob00442a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C20 H16 Br2 O2 S3'
_chemical_formula_weight         544.31
_chemical_melting_point          117(2)
_chemical_name_common            'Dibenzyl disulfanylsulfone'
_chemical_name_systematic
1-(4-Bromobenzyl)-2-[(4-bromophenyl)(phenylsulfonyl)methyl]disulfane
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-29 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.033(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1114(13)
_cell_length_b                   5.6423(5)
_cell_length_c                   25.433(2)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.92
_cell_volume                     2005.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            33707
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.650
_exptl_absorpt_coefficient_mu    4.369
_exptl_absorpt_correction_T_max  0.382
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0179
_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)+(0.0102P)²+1.3769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4100
_reflns_number_total             4352
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00442a2.cif
_cod_data_source_block           MWIV41_2fa
_cod_depositor_comments          'Adding full bibliography for 7157444.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157444
_shelx_shelxl_version_number     2014/7
_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br2 Br 0.09483(2) -0.00381(3) 0.73355(2) 0.01869(6) Uani 1 1 d . . . . .
Br1 Br 0.62986(2) -0.07648(3) 0.34679(2) 0.02089(6) Uani 1 1 d . . . . .
S1 S 0.16706(3) 0.14020(7) 0.41758(2) 0.01582(8) Uani 1 1 d . . . . .
S2 S 0.29816(3) 0.27275(7) 0.51389(2) 0.01710(9) Uani 1 1 d . . . . .
S3 S 0.28983(3) 0.61266(7) 0.53819(2) 0.02051(9) Uani 1 1 d . . . . .
O1 O 0.18374(8) -0.1110(2) 0.42360(4) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.09194(8) 0.2483(2) 0.44223(4) 0.0225(2) Uani 1 1 d . . . . .
C6 C 0.18025(11) 0.0490(3) 0.31350(6) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.2123 -0.0927 0.3259 0.020 Uiso 1 1 calc R U . . .
C18 C 0.11228(11) 0.1988(3) 0.67589(6) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.14099(12) 0.4925(3) 0.59216(6) 0.0178(3) Uani 1 1 d . . . . .
C5 C 0.16495(11) 0.1019(3) 0.25952(6) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.1862 -0.0045 0.2347 0.022 Uiso 1 1 calc R U . . .
C11 C 0.52103(11) 0.0420(3) 0.37472(6) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.36151(11) 0.2033(3) 0.41646(5) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.08691(12) 0.4671(3) 0.27788(6) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.0553 0.6091 0.2654 0.023 Uiso 1 1 calc R U . . .
C2 C 0.10131(11) 0.4168(3) 0.33199(6) 0.0178(3) Uani 1 1 d . . . . .
H2 H 0.0799 0.5232 0.3568 0.021 Uiso 1 1 calc R U . . .
C20 C 0.08959(11) 0.2830(3) 0.58286(6) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.0641 0.2410 0.5475 0.022 Uiso 1 1 calc R U . . .
C1 C 0.14783(11) 0.2071(3) 0.34898(6) 0.0148(3) Uani 1 1 d . . . . .
C12 C 0.48134(11) 0.2575(3) 0.35786(6) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.5083 0.3498 0.3325 0.022 Uiso 1 1 calc R U . . .
C7 C 0.27732(11) 0.2970(3) 0.44096(6) 0.0156(3) Uani 1 1 d . . . . .
H7 H 0.2683 0.4681 0.4313 0.019 Uiso 1 1 calc R U . . .
C17 C 0.16245(11) 0.4080(3) 0.68662(6) 0.0173(3) Uani 1 1 d . . . . .
H17 H 0.1864 0.4512 0.7221 0.021 Uiso 1 1 calc R U . . .
C4 C 0.11864(11) 0.3102(3) 0.24211(6) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.1085 0.3459 0.2053 0.022 Uiso 1 1 calc R U . . .
C19 C 0.07488(11) 0.1340(3) 0.62454(6) 0.0172(3) Uani 1 1 d . . . . .
H19 H 0.0399 -0.0093 0.6180 0.021 Uiso 1 1 calc R U . . .
C9 C 0.40277(11) -0.0144(3) 0.43257(6) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.3761 -0.1074 0.4580 0.021 Uiso 1 1 calc R U . . .
C16 C 0.17703(12) 0.5532(3) 0.64447(6) 0.0194(3) Uani 1 1 d . . . . .
H16 H 0.2121 0.6963 0.6512 0.023 Uiso 1 1 calc R U . . .
C10 C 0.48252(11) -0.0960(3) 0.41175(6) 0.0173(3) Uani 1 1 d . . . . .
H10 H 0.5105 -0.2443 0.4227 0.021 Uiso 1 1 calc R U . . .
C14 C 0.16403(13) 0.6448(3) 0.54712(6) 0.0229(3) Uani 1 1 d . . . . .
H14A H 0.1506 0.8128 0.5546 0.027 Uiso 1 1 calc R U . . .
H14B H 0.1228 0.5986 0.5140 0.027 Uiso 1 1 calc R U . . .
C13 C 0.40070(11) 0.3370(3) 0.37895(6) 0.0168(3) Uani 1 1 d . . . . .
H13 H 0.3723 0.4842 0.3675 0.020 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
O2 S1 O1 119.31(7) . . ?
O2 S1 C1 108.56(7) . . ?
O1 S1 C1 108.35(7) . . ?
O2 S1 C7 107.46(7) . . ?
O1 S1 C7 108.93(7) . . ?
C1 S1 C7 103.02(7) . . ?
C7 S2 S3 103.25(5) . . ?
C14 S3 S2 103.34(6) . . ?
C1 C6 C5 118.85(14) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C17 C18 C19 121.80(14) . . ?
C17 C18 Br2 118.58(11) . . ?
C19 C18 Br2 119.62(12) . . ?
C20 C15 C16 118.82(14) . . ?
C20 C15 C14 121.31(15) . . ?
C16 C15 C14 119.73(15) . . ?
C4 C5 C6 119.85(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C12 C11 C10 121.56(15) . . ?
C12 C11 Br1 120.48(12) . . ?
C10 C11 Br1 117.95(12) . . ?
C13 C8 C9 119.29(14) . . ?
C13 C8 C7 120.25(14) . . ?
C9 C8 C7 120.42(13) . . ?
C4 C3 C2 120.15(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C1 C2 C3 118.51(14) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C15 C20 C19 120.94(14) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C6 C1 C2 121.83(14) . . ?
C6 C1 S1 118.94(12) . . ?
C2 C1 S1 119.22(12) . . ?
C11 C12 C13 118.67(14) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C7 S1 112.41(10) . . ?
C8 C7 S2 111.40(10) . . ?
S1 C7 S2 107.61(8) . . ?
C8 C7 H7 108.4 . . ?
S1 C7 H7 108.4 . . ?
S2 C7 H7 108.4 . . ?
C18 C17 C16 118.59(14) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C5 C4 C3 120.81(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C18 C19 C20 118.72(15) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C10 C9 C8 120.47(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C17 C16 C15 121.11(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C9 C10 C11 119.17(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C15 C14 S3 110.77(11) . . ?
C15 C14 H14A 109.5 . . ?
S3 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
S3 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C8 C13 C12 120.82(15) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
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
Br2 C18 1.9022(15) . ?
Br1 C11 1.9014(16) . ?
S1 O2 1.4403(12) . ?
S1 O1 1.4415(12) . ?
S1 C1 1.7686(15) . ?
S1 C7 1.8162(16) . ?
S2 C7 1.8420(15) . ?
S2 S3 2.0234(6) . ?
S3 C14 1.8299(18) . ?
C6 C1 1.391(2) . ?
C6 C5 1.392(2) . ?
C6 H6 0.9500 . ?
C18 C17 1.384(2) . ?
C18 C19 1.388(2) . ?
C15 C20 1.389(2) . ?
C15 C16 1.399(2) . ?
C15 C14 1.504(2) . ?
C5 C4 1.387(2) . ?
C5 H5 0.9500 . ?
C11 C12 1.382(2) . ?
C11 C10 1.390(2) . ?
C8 C13 1.390(2) . ?
C8 C9 1.396(2) . ?
C8 C7 1.512(2) . ?
C3 C4 1.387(2) . ?
C3 C2 1.392(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.392(2) . ?
C2 H2 0.9500 . ?
C20 C19 1.391(2) . ?
C20 H20 0.9500 . ?
C12 C13 1.398(2) . ?
C12 H12 0.9500 . ?
C7 H7 1.0000 . ?
C17 C16 1.387(2) . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C19 H19 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353356
