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_7159568
_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 H20 O3 S2'
_chemical_formula_sum            'C22 H20 O3 S2'
_chemical_formula_weight         396.50
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2022-10-28 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.71(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.264(3)
_cell_length_b                   8.475(2)
_cell_length_c                   22.934(6)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.3150
_cell_measurement_theta_min      4.2560
_cell_volume                     1988.2(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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 2018/3 (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 0.997
_diffrn_measured_fraction_theta_max 0.841
_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     20.00  71.00   1.00    5.00    --   15.65  57.00 120.00   51
  2  \w    -25.00  22.00   1.00    5.00    --  -16.43 -99.00 150.00   47
  3  \w    -75.00  -2.00   1.00    5.00    --  -16.43 -57.00 -90.00   73
  4  \w    -27.00  44.00   1.00    5.00    --  -16.43  57.00-180.00   71
;
_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      -0.0038596000
_diffrn_orient_matrix_UB_12      -0.0828056000
_diffrn_orient_matrix_UB_13      -0.0039371000
_diffrn_orient_matrix_UB_21      -0.0244435000
_diffrn_orient_matrix_UB_22      -0.0080651000
_diffrn_orient_matrix_UB_23      0.0279861000
_diffrn_orient_matrix_UB_31      -0.0647580000
_diffrn_orient_matrix_UB_32      0.0080288000
_diffrn_orient_matrix_UB_33      -0.0129059000
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10272
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         3.513
_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  0.75828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.7163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2793
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01249b2.cif
_cod_data_source_block           exp_10412
_cod_depositor_comments
'Adding full bibliography for 7159568--7159569.cif.'
_cod_database_code               7159568
_shelx_shelxl_version_number     2018/3
_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:
 C1(H1), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              98340
_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.780