Recyclable iodine-catalyzed oxidative C–H chalcogenation of 1,1-diarylethenes in water: green synthesis of trisubstituted vinyl sulfides and selenides
Mukherjee, Nilanjana; Chatterjee, Tanmay; Green Chemistry 25 (2023) 8798–8807; doi:10.1039/D3GC02999A

data_7247432
_publ_section_title
;
 Recyclable iodine-catalyzed oxidative C--H chalcogenation of
 1,1-diarylethenes in water: green synthesis of trisubstituted vinyl
 sulfides and selenides
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              8798
_journal_page_last               8807
_journal_paper_doi               10.1039/D3GC02999A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H18 S'
_chemical_formula_sum            'C17 H18 S'
_chemical_formula_weight         254.37
_chemical_name_systematic        NM-1287
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2023-05-09 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4617(5)
_cell_length_b                   11.8672(7)
_cell_length_c                   13.2190(8)
_cell_measurement_reflns_used    2648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1160
_cell_measurement_theta_min      4.9460
_cell_volume                     1484.28(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.957
_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    -19.00  25.00   0.50   10.00    --    0.00  37.00-180.00   88
  2  \w     53.00  79.00   0.50   10.00    --    0.00  37.00-180.00   52
  3  \w     39.00  82.00   0.50   10.00    --    0.00  77.00-180.00   86
  4  \w    140.00 166.00   0.50   40.00    --  107.20  45.00  90.00   52
  5  \w     29.00  58.00   0.50   40.00    --  107.20 -30.00  30.00   58
  6  \w     63.00 125.00   0.50   40.00    --  107.20 -30.00  30.00  124
  7  \w     18.00 132.00   0.50   40.00    --  107.20 -61.00 -60.00  228
  8  \w     88.00 115.00   0.50   40.00    --  107.20  61.00 -90.00   54
  9  \w    114.00 181.00   0.50   40.00    --  107.20  77.00 -60.00  134
 10  \w     88.00 127.00   0.50   40.00    --  107.20  45.00  90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1109406000
_diffrn_orient_matrix_UB_12      -0.0756063000
_diffrn_orient_matrix_UB_13      -0.0514351000
_diffrn_orient_matrix_UB_21      -0.0427378000
_diffrn_orient_matrix_UB_22      0.0477882000
_diffrn_orient_matrix_UB_23      -0.1039694000
_diffrn_orient_matrix_UB_31      0.1113287000
_diffrn_orient_matrix_UB_32      0.0939978000
_diffrn_orient_matrix_UB_33      0.0114561000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.763
_diffrn_reflns_theta_min         5.008
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             544
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0614P)^2^+0.1737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                2395
_reflns_number_total             2754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02999a2.cif
_cod_data_source_block           nm-1287-crysalis
_cod_depositor_comments          'Adding full bibliography for 7247432.cif.'
_cod_database_code               7247432
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009)
2.b Idealised Me refined as rotating group:
 C00G(H00b,H00d,H00g), C1(H1a,H1b,H1c)
;
_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 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.546