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_1564327
_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_absolute_configuration unk
_chemical_formula_moiety         'C13 H14 F4 O2 S'
_chemical_formula_sum            'C13 H14 F4 O2 S'
_chemical_formula_weight         310.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.425(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1315(7)
_cell_length_b                   8.3917(5)
_cell_length_c                   15.5384(10)
_cell_measurement_reflns_used    7098
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.487
_cell_measurement_theta_min      4.212
_cell_volume                     1368.85(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8209
_diffrn_reflns_point_group_measured_fraction_full 0.733
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.482
_diffrn_reflns_theta_min         4.211
_diffrn_source                   'sealed tube'
_diffrn_source_current           0.64
_diffrn_source_power             0.0286272
_diffrn_source_voltage           44.73
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0654 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.0171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.472
_reflns_Friedel_fraction_full    0.474
_reflns_Friedel_fraction_max     0.467
_reflns_number_gt                3604
_reflns_number_total             3662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03315h2.cif
_cod_data_source_block           ykd
_cod_database_code               1564327
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.749
_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. Rigid bond restraints
 S1, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C13A(H13A)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C1A(H1AA,H1AB,H1AC),
 C6A(H6AA,H6AB,H6AC), C7A(H7AA,H7AB,H7AC)
;
_shelx_res_checksum              69774
_shelx_hkl_checksum              31542
_olex2_submission_special_instructions 'No special instructions were received'