Oxidation-Induced β-Selective C–H Bond Functionalization: Thiolation and Selenation of N-Heterocycles
Wang, Huamin; Li, Yongli; Lu, Qingquan; Yu, Mingming; Bai, Xudong; Wang, Shengchun; Cong, Hengjiang; Zhang, Heng; Lei, Aiwen; ACS Catalysis 9 (2019) 1888–; doi:10.1021/acscatal.8b05054

data_4514889
_publ_section_title
;
 Oxidation-Induced \b-Selective C--H Bond Functionalization: Thiolation
 and Selenation of N-Heterocycles
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1888
_journal_paper_doi               10.1021/acscatal.8b05054
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C16 H12 Cl N S'
_chemical_formula_weight         285.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6912(12)
_cell_length_b                   23.747(4)
_cell_length_c                   7.5180(13)
_cell_measurement_reflns_used    4500
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.67
_cell_measurement_theta_min      3.72
_cell_volume                     1373.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4302
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        63.683
_diffrn_reflns_theta_max         63.683
_diffrn_reflns_theta_min         6.048
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.737
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.114(19)
_refine_ls_extinction_coef       0.0067(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0971P)^2^+0.2954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.326
_reflns_Friedel_fraction_full    0.377
_reflns_Friedel_fraction_max     0.377
_reflns_number_gt                1556
_reflns_number_total             1582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05054_si_002.cif
_cod_data_source_block           x_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514889
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.706
_shelx_estimated_absorpt_t_max   0.807
_shelx_res_checksum              4473
_shelx_hkl_checksum              38552