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_4032267
_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         'C74 H93 I N2 O4 S'
_chemical_formula_sum            'C74 H93 I N2 O4 S'
_chemical_formula_weight         1233.46
_chemical_name_systematic
;
{(t-BuC6H4)3CCONH}2C6H3SI-DME
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-01-28
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3441(4)
_cell_length_b                   40.3816(9)
_cell_length_c                   11.4691(3)
_cell_measurement_reflns_used    30734
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.02
_cell_volume                     6643.3(3)
_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-2016/6 (Sheldrick, 2016)'
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            48545
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.014
_diffrn_source
;
 MicroMax-007HF microfocus rotating anode X-ray generator
;
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5931
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+7.4123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4277
_reflns_number_total             5931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00160_si_002.cif
_cod_data_source_block           Ar1SI-DME
_cod_database_code               4032267
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.983
_shelx_hkl_checksum              83867