The solvent-controlled chemoselective construction of C-S/S-S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones.
Zhang, Xi; Wang, Tong-Lin; Liu, Xiao-Jun; Wang, Xi-Cun; Quan, Zheng-Jun; Organic & biomolecular chemistry 17 (2019) 2379–2383; doi:10.1039/c8ob02971g

data_7157184
_publ_section_title
;
 The solvent-controlled chemoselective construction of C-S/S-S bonds via
 the Michael reaction/thiol coupling of quinoline-2-thiones.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2379
_journal_page_last               2383
_journal_paper_doi               10.1039/c8ob02971g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C19 H16 N2 S'
_chemical_formula_weight         304.40
_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'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc210g1l
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-11-07 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.192(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.5086(4)
_cell_length_b                   17.1346(8)
_cell_length_c                   22.5907(11)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      3.25
_cell_volume                     3251.2(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      291(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            67074
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.253
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0153(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5659
_refine_ls_number_restraints     492
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0540P)^2^+0.6077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5101
_reflns_number_total             5659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02971g2.cif
_cod_data_source_block           cu_20180905A_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157184
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              27393