Metal-free hydrosulfonylation of α,β-unsaturated ketones: synthesis and application of γ-keto sulfones
Cheng, Xiufang; Wang, Shuo; Wei, Yibo; Wang, Huamin; Lin, Ying-Wu; RSC Advances 12 (2022) 35649–35654; doi:10.1039/D2RA06784F

data_7246004
_publ_section_title
;
 Metal-free hydrosulfonylation of \a,\b-unsaturated ketones: synthesis and
 application of \g-keto sulfones
;
_journal_issue                   55
_journal_name_full               'RSC Advances'
_journal_page_first              35649
_journal_page_last               35654
_journal_paper_doi               10.1039/D2RA06784F
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 F O5 S'
_chemical_formula_sum            'C21 H19 F O5 S'
_chemical_formula_weight         402.42
_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             2022-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9808(7)
_cell_length_b                   10.9396(3)
_cell_length_c                   10.3118(4)
_cell_measurement_reflns_used    8509
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.36
_cell_volume                     1947.84(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21333
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.775
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.9319.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4272
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0433P)^2^+0.7916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3672
_reflns_number_total             4272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra06784f2.cif
_cod_data_source_block           mo_220621_ws_2_1
_cod_database_code               7246004
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-C20 \\sim O5-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 O5-C21 \\sim O5-C21A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O5 \\sim C20 \\sim C21 \\sim C20A \\sim C21A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
4. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C20(H20A,H20B), C20A(H20C,H20D)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              5027
_olex2_submission_special_instructions 'No special instructions were received'