# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MWIV41_2fa
_database_code_depnum_ccdc_archive 'CCDC 1987266'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;Ramanujan Fellow at CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2020-02-29 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(4-Bromobenzyl)-2-[(4-bromophenyl)(phenylsulfonyl)methyl]disulfane
_chemical_name_common            'Dibenzyl disulfanylsulfone'
_chemical_melting_point          117(2)
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br2 O2 S3'
_chemical_formula_weight         544.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   14.1114(13)
_cell_length_b                   5.6423(5)
_cell_length_c                   25.433(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.033(3)
_cell_angle_gamma                90
_cell_volume                     2005.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    4.369
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_T_max  0.382
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33707
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4352
_reflns_number_gt                4100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0102P)²+1.3769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4352
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0432
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_
_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 . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.057

