Trace water in a BF<sub>3</sub>·OEt<sub>2</sub> system: a facile access to sulfinyl alkenylsulfones from alkynes and sodium sulfinates.
Yu, Shi-Wei; Chen, Zu-Jia; Chen, Zhao-Hua; Chen, Si-Hong; Yang, Kai; Xu, Wen-Jin; Wang, Zhao-Yang; Organic & biomolecular chemistry 21 (2023) 7776–7781; doi:10.1039/d3ob01249b

data_7159569
_publ_section_title
;
 Trace water in a BF<sub>3</sub>&#xb7;OEt<sub>2</sub> system: a facile
 access to sulfinyl alkenylsulfones from alkynes and sodium sulfinates.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7776
_journal_page_last               7781
_journal_paper_doi               10.1039/d3ob01249b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 F O3 S2'
_chemical_formula_sum            'C22 H19 F O3 S2'
_chemical_formula_weight         414.49
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                101.895(6)
_cell_angle_beta                 92.033(7)
_cell_angle_gamma                91.343(7)
_cell_formula_units_Z            4
_cell_length_a                   8.4367(9)
_cell_length_b                   10.2011(7)
_cell_length_c                   24.4853(15)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.1900
_cell_measurement_theta_min      2.3110
_cell_volume                     2059.7(3)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -52.00  41.60   0.90    5.00    --   15.65 -77.00 -90.00  104
  2  \w    -25.00  22.70   0.90    5.00    --  -16.43 -99.00-180.00   53
  3  \w     -2.00  70.00   0.90    5.00    --   15.65  38.00-180.00   80
  4  \w    -10.00  80.00   0.90    5.00    --   15.65  77.00  30.00  100
  5  \w     49.00  75.10   0.90    5.00    --   15.65 178.00 -30.00   29
  6  \w    -86.00 -32.00   0.90    5.00    --  -16.43 -38.00 -60.00   60
  7  \w     -6.00  26.40   0.90    5.00    --   15.65 -57.00 150.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0388002000
_diffrn_orient_matrix_UB_12      -0.0212284000
_diffrn_orient_matrix_UB_13      -0.0254005000
_diffrn_orient_matrix_UB_21      0.0694974000
_diffrn_orient_matrix_UB_22      0.0369630000
_diffrn_orient_matrix_UB_23      0.0119029000
_diffrn_orient_matrix_UB_31      0.0273652000
_diffrn_orient_matrix_UB_32      -0.0568971000
_diffrn_orient_matrix_UB_33      0.0095410000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87276
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0432P)^2^+0.4433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4818
_reflns_number_total             7242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01249b2.cif
_cod_data_source_block           exp_12199
_cod_depositor_comments
'Adding full bibliography for 7159568--7159569.cif.'
_cod_database_code               7159569
_shelx_shelxl_version_number     2019/2
_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 Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C14(H14), C16(H16), C18(H18), C22(H22), C24(H24),
 C26(H26), C28(H28), C30(H30), C32(H32), C38(H38), C44(H44), C5(H5), C7(H7),
 C13(H13), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29), C33(H33), C35(H35),
  C39(H39), C41(H41), C43(H43)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C9(H9A,H9B,H9C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              11701
_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 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.800