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_1564326
_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         'C14 H17 F3 O3 S'
_chemical_formula_sum            'C14 H17 F3 O3 S'
_chemical_formula_weight         322.33
_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             2021-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-19 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.185(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8048(3)
_cell_length_b                   12.4774(5)
_cell_length_c                   17.3856(6)
_cell_measurement_reflns_used    8301
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.9190
_cell_measurement_theta_min      3.4110
_cell_volume                     1473.87(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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    -76.00 -51.00   1.00    4.00    --    0.20 -57.00   0.00   25
  2  \w     46.00  72.00   1.00    4.00    --    0.20  57.00-180.00   26
  3  \w    -16.00  17.00   1.00    4.00    --    0.20  38.00 -60.00   33
  4  \w     24.00  90.00   1.00    4.00    --    0.20  38.00 -60.00   66
  5  \w    -89.00  -9.00   1.00    4.00    --    0.20 -57.00  60.00   80
  6  \w     -4.00  24.00   1.00    4.00    --    0.20 -57.00  60.00   28
  7  \w    -34.00  31.00   1.00    4.00    --    0.20 -77.00-150.00   65
  8  \w    -18.00  80.00   1.00    4.00    --    0.20  38.00  30.00   98
  9  \w    -15.00  10.00   1.00    4.00    --    0.20 -38.00   0.00   25
 10  \w     -4.00  21.00   1.00    4.00    --    0.20 -24.00 152.28   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0368824000
_diffrn_orient_matrix_UB_12      -0.0312840000
_diffrn_orient_matrix_UB_13      0.0316874000
_diffrn_orient_matrix_UB_21      -0.0021476000
_diffrn_orient_matrix_UB_22      0.0456935000
_diffrn_orient_matrix_UB_23      0.0241957000
_diffrn_orient_matrix_UB_31      -0.0976291000
_diffrn_orient_matrix_UB_32      -0.0128207000
_diffrn_orient_matrix_UB_33      0.0089917000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25409
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.265
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0556P)^2^+0.2975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2946
_reflns_number_total             3377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03315h2.cif
_cod_data_source_block           exp_1870
_cod_database_code               1564326
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              69277
_shelx_hkl_checksum              19653
_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 1.804
_oxdiff_exptl_absorpt_empirical_full_min 0.602