Electro-oxidative coupling of Bunte salts with aryldiazonium tetrafluoroborates: a benign access to unsymmetrical sulfoxides.
Kumar, Saurabh; Chand, Shiv; Singh, Krishna Nand; Organic & biomolecular chemistry 22 (2024) 850–856; doi:10.1039/d3ob01955a

data_7159721
_publ_section_title
;
 Electro-oxidative coupling of Bunte salts with aryldiazonium
 tetrafluoroborates: a benign access to unsymmetrical sulfoxides.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              850
_journal_page_last               856
_journal_paper_doi               10.1039/d3ob01955a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H12 Cl2 O S'
_chemical_formula_sum            'C14 H12 Cl2 O S'
_chemical_formula_weight         299.20
_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_primary     iterative
_audit_creation_date             2023-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-23 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.205(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7326(5)
_cell_length_b                   16.7916(19)
_cell_length_c                   14.3441(12)
_cell_measurement_reflns_used    729
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.2900
_cell_measurement_theta_min      4.0510
_cell_volume                     1379.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9738
_diffrn_measured_fraction_theta_max 0.9738
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00 -39.00   1.00    1.00    --    0.00 178.00 -30.00   35
  2  \w     33.00  77.00   1.00    1.00    --    0.00-178.00 -30.00   44
  3  \w   -124.00 -79.00   1.00    1.01    --  -56.00 -99.00 -60.00   45
  4  \w    -81.00  -3.00   1.00    1.01    --  -56.00  37.00  90.00   78
  5  \w    -97.00 -26.00   1.00    1.01    --  -56.00 -77.00 -60.00   71
  6  \w   -121.00 -95.00   1.00    1.01    --  -56.00 -99.00  60.00   26
  7  \w    -75.00 -22.00   1.00    1.01    --  -56.00  57.00 -60.00   53
  8  \w     51.00  78.00   1.00    1.01    --  112.00 -25.00 120.00   27
  9  \w     85.00 112.00   1.00    1.01    --  112.00-111.00 -90.00   27
 10  \w     99.00 145.00   1.00    1.01    --  112.00 178.00  90.00   46
 11  \w     79.00 145.00   1.00    1.01    --  112.00 111.00-120.00   66
 12  \w     43.00  74.00   1.00    1.01    --  112.00 178.00  90.00   31
 13  \w     45.00 130.00   1.00    1.01    --  112.00 -50.00  60.00   85
 14  \w     47.00 106.00   1.00    1.01    --  112.00-111.00-120.00   59
 15  \w     88.00 142.00   1.00    1.01    --  112.00 -25.00 120.00   54
 16  \w     51.00 136.00   1.00    1.01    --  112.00 -37.00 -90.00   85
 17  \w    145.00 177.00   1.00    1.01    --  112.00  37.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1911715000
_diffrn_orient_matrix_UB_12      -0.0017850000
_diffrn_orient_matrix_UB_13      -0.0785463000
_diffrn_orient_matrix_UB_21      -0.0941732000
_diffrn_orient_matrix_UB_22      0.0805484000
_diffrn_orient_matrix_UB_23      0.0336263000
_diffrn_orient_matrix_UB_31      0.1642699000
_diffrn_orient_matrix_UB_32      0.0439638000
_diffrn_orient_matrix_UB_33      -0.0650558000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5008
_diffrn_reflns_theta_full        72.3312
_diffrn_reflns_theta_max         72.33
_diffrn_reflns_theta_min         4.06
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00976
_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    1.4404
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             621.5854
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.7384
_refine_diff_density_min         -0.4572
_refine_diff_density_rms         0.1162
_refine_ls_d_res_high            0.8091
_refine_ls_d_res_low             10.9018
_refine_ls_goodness_of_fit_ref   1.0169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0169
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1162P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2285
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -5
_reflns_number_gt                1721
_reflns_number_total             2644
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob01955a2.cif
_cod_data_source_block           saurabh-27-02-second
_cod_depositor_comments          'Adding full bibliography for 7159721.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159721
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C9(H9), C13(H13), C12(H12), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_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 51.440
_oxdiff_exptl_absorpt_empirical_full_min 0.545