Metal-free cascade rearrangement/radical addition/oxidative C–H annulation of propargyl alcohols with sodium sulfinates: access to 2-sulfenylindenones
Liu, Changqing; Wang, Bo; Guo, Ziyi; Zhang, Jitan; Xie, Meihua; Organic Chemistry Frontiers 6 (2019) 2796–; doi:10.1039/C9QO00688E

data_1555010
_publ_section_title
;
 Metal-free cascade rearrangement/radical addition/oxidative C--H
 annulation of propargyl alcohols with sodium sulfinates: access to
 2-sulfenylindenones
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2796
_journal_paper_doi               10.1039/C9QO00688E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C22 H14 Cl F O S'
_chemical_formula_weight         380.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-01-07 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.3370(10)
_cell_angle_beta                 91.5180(10)
_cell_angle_gamma                104.3610(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3464(2)
_cell_length_b                   8.5371(3)
_cell_length_c                   15.0907(5)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.94
_cell_volume                     911.69(5)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36064
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.866
_exptl_absorpt_coefficient_mu    0.341
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3454
_reflns_number_total             4161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00688e2.cif
_cod_data_source_block           mo_20180411c_0m
_cod_database_code               1555010
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.920
_shelx_estimated_absorpt_t_max   0.935
_shelx_res_checksum              57823
_shelx_hkl_checksum              43161