One-pot thiol-free synthetic approach to sulfides, and sulfoxides selectively
Kotha, Sambasivarao; Gupta, Naveen Kumar; Ansari, Saima; RSC Advances 12 (2022) 25154–25162; doi:10.1039/D2RA04872H

data_7245444
_publ_section_title
;
 One-pot thiol-free synthetic approach to sulfides, and sulfoxides
 selectively
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              25154
_journal_page_last               25162
_journal_paper_doi               10.1039/D2RA04872H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C9 H9 Br S'
_chemical_formula_sum            'C9 H9 Br S'
_chemical_formula_weight         229.13
_chemical_melting_point          358.0(10)
_chemical_name_systematic        (E)-1,4-bis((4-bromobenzyl)thio)but-2-ene
_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     dual
_audit_creation_date             2021-06-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.622(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5752(12)
_cell_length_b                   6.3230(6)
_cell_length_c                   9.1422(8)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    304.00(10)
_cell_measurement_theta_max      24.5240
_cell_measurement_theta_min      3.7400
_cell_volume                     941.73(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -25.75 154.25   1.00    4.00 -25.75   0.00  73.76    --   180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032916000
_diffrn_orient_matrix_UB_12      0.0931128000
_diffrn_orient_matrix_UB_13      -0.0437786000
_diffrn_orient_matrix_UB_21      -0.0356946000
_diffrn_orient_matrix_UB_22      0.0295917000
_diffrn_orient_matrix_UB_23      0.0276574000
_diffrn_orient_matrix_UB_31      0.0246832000
_diffrn_orient_matrix_UB_32      0.0551535000
_diffrn_orient_matrix_UB_33      0.0595690000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5115
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.456
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0350
_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/[\s^2^(Fo^2^)+(0.0270P)^2^+0.4977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1285
_reflns_number_total             1641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04872h2.cif
_cod_data_source_block           fastscan_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '357-359' was changed to
'358.0(10)' -- 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               7245444
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.487
_shelx_estimated_absorpt_t_min   0.371
_reflns_odcompleteness_completeness 83.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C2(H2), C5(H5), C6(H6)
;
_shelx_res_checksum              18095
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.888