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_1564325
_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         'C12 H13 F3 O4 S'
_chemical_formula_sum            'C12 H13 F3 O4 S'
_chemical_formula_weight         310.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.14(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.086(2)
_cell_length_b                   5.508(2)
_cell_length_c                   12.766(3)
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.08
_cell_volume                     674.0(3)
_computing_cell_refinement       '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 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5559
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.125
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.7433.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0807P)^2^+0.4283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1920
_reflns_number_total             2333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03315h2.cif
_cod_data_source_block           11_a_pl
_cod_database_code               1564325
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(2)
 0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C3(H3)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              96147
_shelx_hkl_checksum              38695
_olex2_submission_special_instructions 'No special instructions were received'