Radical-Mediated Vicinal Addition of Alkoxysulfonyl/Fluorosulfonyl and Trifluoromethyl Groups to Aryl Alkyl Alkynes
Dong, Xinrui; Jiang, Wenhua; Hua, Dexiang; Wang, Xiaohui; Xu, Liang; Wu, Xiaoxing; Chemical Science  (2021) –; doi:10.1039/D1SC03315H

data_1564328
_publ_section_title
;
 Radical-Mediated Vicinal Addition of Alkoxysulfonyl/Fluorosulfonyl and
 Trifluoromethyl Groups to Aryl Alkyl Alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03315H
_journal_year                    2021
_chemical_formula_moiety         'C19 H21 F3 O3 S Si'
_chemical_formula_sum            'C19 H21 F3 O3 S Si'
_chemical_formula_weight         414.51
_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             2021-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.362(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4060(3)
_cell_length_b                   15.9894(6)
_cell_length_c                   34.9562(12)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      44.428
_cell_measurement_theta_min      3.264
_cell_volume                     4127.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            46817
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.092
_diffrn_reflns_theta_min         3.263
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1557 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.6978. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+6.4085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4172
_reflns_number_total             7828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03315h2.cif
_cod_data_source_block           2104122315_0m
_cod_database_code               1564328
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.928
_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:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C20(H20A,
 H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              62598
_shelx_hkl_checksum              78589
_olex2_submission_special_instructions 'No special instructions were received'