B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed regio- and stereoselective thiosulfonylation of terminal alkynes with thiosulfonates.
Qin, Wenjie; Ni, Qian; Jiao, Wenjun; Ma, Yuanhong; Chemical communications (Cambridge, England) 59 (2023) 7951–7954; doi:10.1039/d3cc02151c

data_1569250
_publ_section_title
;
 B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed regio- and
 stereoselective thiosulfonylation of terminal alkynes with
 thiosulfonates.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7951
_journal_page_last               7954
_journal_paper_doi               10.1039/d3cc02151c
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H22 O3 S2, 0.5(C H Cl3)'
_chemical_formula_sum            'C23.5 H22.5 Cl1.5 O3 S2'
_chemical_formula_weight         470.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2fhk9t
_audit_creation_date             2023-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                113.174(4)
_cell_angle_beta                 97.818(3)
_cell_angle_gamma                97.371(3)
_cell_formula_units_Z            4
_cell_length_a                   9.9799(3)
_cell_length_b                   15.1960(6)
_cell_length_c                   16.9612(7)
_cell_measurement_reflns_used    5213
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.2460
_cell_measurement_theta_min      2.9270
_cell_volume                     2295.56(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     58.00 102.00   1.00    1.00    --   34.48  57.00 -30.00   44
  2  \w     36.00 112.00   1.00    6.00    --  105.25 -30.00 -30.00   76
  3  \w     69.00 125.00   1.00    6.00    --  105.25 -30.00-120.00   56
  4  \w     85.00 127.00   1.00    6.00    --  105.25 -30.00-180.00   42
  5  \w     84.00 116.00   1.00    6.00    --  105.25-111.00 -90.00   32
  6  \w     46.00  83.00   1.00    1.00    --   34.48-125.00 -30.00   37
  7  \w    104.00 130.00   1.00    6.00    --  105.25 111.00-120.00   26
  8  \w     35.00  69.00   1.00    6.00    --  105.25 -30.00-180.00   34
  9  \w     38.00 115.00   1.00    6.00    --  105.25 -61.00-120.00   77
 10  \w     36.00  98.00   1.00    6.00    --  105.25 -94.00-150.00   62
 11  \w     39.00  65.00   1.00    6.00    --  105.25-111.00 -90.00   26
 12  \w     48.00 115.00   1.00    6.00    --  105.25-111.00  30.00   67
 13  \w     83.00 108.00   1.00    6.00    --  105.25 -94.00 120.00   25
 14  \w     37.00  86.00   1.00    1.00    --   34.48-125.00 120.00   49
 15  \w     38.00 118.00   1.00    6.00    --  105.25 -45.00  60.00   80
 16  \w     99.00 165.00   1.00    6.00    --  105.25  30.00 150.00   66
 17  \w     38.00 140.00   1.00    6.00    --  105.25 -15.00 120.00  102
 18  \w     39.00 135.00   1.00    6.00    --  105.25 -82.00  46.00   96
 19  \w     24.00  63.00   1.00    1.00    --   34.48 -19.00 150.00   39
 20  \w     23.00  89.00   1.00    1.00    --   34.48  38.00  60.00   66
 21  \w     23.00  84.00   1.00    1.00    --   34.48  38.00 -30.00   61
 22  \w      9.00  87.00   1.00    1.00    --   34.48  77.00-150.00   78
 23  \w    -29.00  51.00   1.00    1.00    --   34.48 -57.00  90.00   80
 24  \w    -37.00  -4.00   1.00    1.00    --   34.48 -19.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0489024000
_diffrn_orient_matrix_UB_12      -0.0841494000
_diffrn_orient_matrix_UB_13      0.0249189000
_diffrn_orient_matrix_UB_21      0.0375055000
_diffrn_orient_matrix_UB_22      -0.0732042000
_diffrn_orient_matrix_UB_23      -0.0828926000
_diffrn_orient_matrix_UB_31      0.1465880000
_diffrn_orient_matrix_UB_32      0.0150309000
_diffrn_orient_matrix_UB_33      0.0519213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14124
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.574
_diffrn_reflns_theta_max         66.574
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0661
_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^)+(0.0689P)^2^+2.0619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5605
_reflns_number_total             7991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02151c2.cif
_cod_data_source_block           exp_2752
_cod_depositor_comments
;
          Adding full bibliography for 1569250.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C47 H45 Cl3 O6 S4'
_cod_original_formula_weight         940.42
_cod_original_formula_moiety         '2(C23 H22 O3 S2), C H Cl3'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2295.56(16)
_cod_database_code               1569250
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 S1 O6'
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 Ternary CH refined with riding coordinates:
 C47(H47)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C29(H29), C30(H30), C33(H33), C34(H34), C36(H36),
 C37(H37), C38(H38), C41(H41), C42(H42), C44(H44), C45(H45), C3(H3), C4(H4),
 C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17),
 C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C46(H46A,H46B,H46C), C1(H1A,H1B,
 H1C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              42856
_shelx_hkl_checksum              92383
_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 1.919
_oxdiff_exptl_absorpt_empirical_full_min 0.663