Regioselective C-H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation.
Kawashima, Hitomi; Yanagi, Tomoyuki; Wu, Chien-Chi; Nogi, Keisuke; Yorimitsu, Hideki; Organic letters 19 (2017) 4552–4555; doi:10.1021/acs.orglett.7b02147

data_1547015
_publ_section_title
;
 Regioselective C-H Sulfanylation of Aryl Sulfoxides by Means of
 Pummerer-Type Activation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4552
_journal_page_last               4555
_journal_paper_doi               10.1021/acs.orglett.7b02147
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C22 H18 O4 S2'
_chemical_formula_sum            'C22 H18 O4 S2'
_chemical_formula_weight         410.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.662(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.878(4)
_cell_length_b                   19.159(5)
_cell_length_c                   7.189(2)
_cell_measurement_reflns_used    974
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.3
_cell_volume                     1849.2(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6043
_diffrn_reflns_point_group_measured_fraction_full 0.768
_diffrn_reflns_point_group_measured_fraction_max 0.765
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.490
_diffrn_reflns_theta_min         6.594
_exptl_absorpt_coefficient_mu    2.843
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.561
_reflns_Friedel_fraction_full    0.555
_reflns_Friedel_fraction_max     0.552
_reflns_number_gt                2389
_reflns_number_total             2617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02147_si_002.cif
_cod_data_source_block           170408TY
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1547015
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.659
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              438
_shelx_hkl_checksum              18022