Direct Sb‒S cross-coupling of halostibines with thiols and disulfides at room temperature
Li, Wei; Li, Shan; Wang, Zixiu; Liu, Chenfu; Ye, Yifei; Chen, Yujing; Xiong, Yuyan; lei, jian; Organic & Biomolecular Chemistry  (2021) –; doi:10.1039/D1OB00959A

data_7158128
_publ_section_title
;
 Direct Sb--S cross-coupling of halostibines with thiols and disulfides at
 room temperature
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB00959A
_journal_year                    2021
_chemical_formula_moiety         'C26 H28 N S Sb'
_chemical_formula_sum            'C26 H28 N S Sb'
_chemical_formula_weight         508.30
_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_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-28
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-01-31 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.451(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7657(6)
_cell_length_b                   19.2142(13)
_cell_length_c                   13.3556(9)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.0860
_cell_measurement_theta_min      2.6220
_cell_volume                     2204.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -11.00  21.00   1.00    5.60    --   11.90  38.00 120.00   32
  2  \w     57.00  84.00   1.00    5.60    --   11.90  38.00 120.00   27
  3  \w    -13.00  30.00   1.00    5.60    --  -11.27 -99.00  30.00   43
  4  \w    -61.00  44.00   1.00    5.60    --   11.90 -77.00-180.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147471000
_diffrn_orient_matrix_UB_12      -0.0204360000
_diffrn_orient_matrix_UB_13      0.0450546000
_diffrn_orient_matrix_UB_21      0.0250495000
_diffrn_orient_matrix_UB_22      0.0302082000
_diffrn_orient_matrix_UB_23      0.0292231000
_diffrn_orient_matrix_UB_31      -0.0772975000
_diffrn_orient_matrix_UB_32      0.0059292000
_diffrn_orient_matrix_UB_33      0.0066320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.882
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0304P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3135
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00959a2.cif
_cod_data_source_block           xray4
_cod_database_code               7158128
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              6393
_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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.602