Nickel-catalyzed directed sulfenylation of sp2 and sp3 C-H bonds
Xiaohan Ye; Jeffrey L. Petersen; Xiaodong Shi; Chem.Commun. 51 (2015) 7863–; doi:10.1039/C5cc01970B

data_7117067
_publ_section_title
;
 Nickel-catalyzed directed sulfenylation of sp2 and sp3 C-H bonds
;
_journal_name_full               Chem.Commun.
_journal_page_first              7863
_journal_paper_doi               10.1039/C5cc01970B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C22 H15 Cl N2 O S'
_chemical_formula_weight         390.87
_chemical_name_systematic
3-chloro-2-(phenylthio)-N-(quinolin-8-yl)benzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-03-05 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.3945(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0459(5)
_cell_length_b                   10.3781(5)
_cell_length_c                   15.4051(7)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      32.5824
_cell_measurement_theta_min      3.2223
_cell_volume                     1837.78(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed-chi'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28740
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.77
_diffrn_source_type              fine-focus
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.607
_exptl_crystal_size_min          0.526
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0835P)^2^+1.1019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                3444
_reflns_number_total             4214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01970b2.cif
_cod_data_source_block           Ia
_cod_database_code               7117067
_shelx_res_checksum              75318