Cu(OTf)2-mediated C(sp2)–H arylsulfonylation of enamides via the insertion of sulfur dioxide
Zhu, Tong-Hao; Zhang, Xiao-Chen; Zhao, Kai; Loh, Teck-Peng; Organic Chemistry Frontiers 6 (2019) 94–; doi:10.1039/C8QO01144C

data_1554519
_publ_section_title
;
 Cu(OTf)2-mediated C(sp2)--H arylsulfonylation of enamides via the
 insertion of sulfur dioxide
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              94
_journal_paper_doi               10.1039/C8QO01144C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C23 H21 N O3 S'
_chemical_formula_weight         391.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-08-17 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.005(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3257(7)
_cell_length_b                   15.1988(12)
_cell_length_c                   16.3404(13)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.90
_cell_volume                     2059.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.970
_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  0.0537
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13021
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         3.895
_exptl_absorpt_coefficient_mu    0.180
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4422
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0450
_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^)+(0.1155P)^2^+0.1598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4077
_reflns_number_total             4422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01144c2.cif
_cod_data_source_block           mo_zthso2a_0m
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               1554519
_shelxl_version_number           2014-3
_shelx_res_checksum              57046
_shelx_hkl_checksum              5131