Snapshot of Oxidation of Thiolate by Diiodine: Stabilization of Intermediate by NH···S Hydrogen Bonds.
Okamura, Taka-Aki; Kaga, Toshihisa; Yamashita, Satoshi; Furuya, Ryosuke; Onitsuka, Kiyotaka; The Journal of organic chemistry 82 (2017) 2187–2192; doi:10.1021/acs.joc.7b00160

data_4032265
_publ_section_title
;
 Snapshot of Oxidation of Thiolate by Diiodine: Stabilization of
 Intermediate by NH&#x00B7;&#x00B7;&#x00B7;S Hydrogen Bonds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2187
_journal_page_last               2192
_journal_paper_doi               10.1021/acs.joc.7b00160
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C81.5 H108.25 N4.75 O2 S'
_chemical_formula_sum            'C81.5 H108.25 N4.75 O2 S'
_chemical_formula_weight         1218.53
_chemical_name_systematic
;
(NEt4)[SC6H3{NHCOC(C6H4-t-Bu)3}2]-1.75CH3CN
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.596(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.6286(14)
_cell_length_b                   14.3600(6)
_cell_length_c                   19.9963(9)
_cell_measurement_reflns_used    24777
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.04
_cell_volume                     7474.0(7)
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2015)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2015)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1248
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55344
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.036
_diffrn_source
;
 MicroMax-007HF microfocus rotating anode X-ray generator
;
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2650
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     900
_refine_ls_number_reflns         13128
_refine_ls_number_restraints     411
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.0808
_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^)+(0.0789P)^2^+3.6169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.2085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6739
_reflns_number_total             13128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00160_si_002.cif
_cod_data_source_block           (NEt4)[Ar1S]-1.75CH3CN
_cod_original_formula_sum        'C81.50 H108.25 N4.75 O2 S'
_cod_database_code               4032265
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              14939