Preparation of thioamides from alkyl bromides, nitriles, and hydrogen sulfide through a thio-Ritter-type reaction
Tang, Shi-Zhong; Xiang, Kai; Ye, Rui; Chen, Meng-En; Yu, Jian-Chang; He, Zhi-Juan; Zhang, Fu-Min; Chemical Communications  (2022) –; doi:10.1039/D2CC04210J

data_7130711
_publ_section_title
;
 Preparation of thioamides from alkyl bromides, nitriles, and hydrogen
 sulfide through a thio-Ritter-type reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04210J
_journal_year                    2022
_chemical_formula_moiety         'C14 H23 N S'
_chemical_formula_sum            'C14 H23 N S'
_chemical_formula_weight         237.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-26 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9195(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.57483(18)
_cell_length_b                   11.2206(2)
_cell_length_c                   10.30302(15)
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.7890
_cell_measurement_theta_min      3.8380
_cell_volume                     1334.99(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     62.00 117.00   0.50    0.05    --   47.57 148.00-143.00  110
  2  \w     61.00  87.00   0.50    0.10    --  107.75 148.00-143.00   52
  3  \w    102.00 127.00   0.50    0.10    --  107.75 123.00  51.00   50
  4  \w     88.00 124.00   0.50    0.10    --  107.75 125.00  90.00   72
  5  \w    135.00 174.00   0.50    0.10    --  107.75 125.00  90.00   78
  6  \w     48.00  73.00   0.50    0.10    --  107.75-123.00 -28.00   50
  7  \w     37.00  64.00   0.50    0.10    --  107.75-148.00 167.00   54
  8  \w     86.00 128.00   0.50    0.10    --  107.75-148.00 167.00   84
  9  \w     44.00  69.00   0.50    0.05    --   47.57-148.00 167.00   50
 10  \w    -24.00  18.00   0.50    0.05    --   47.57 -19.00   0.00   84
 11  \w    -17.00  23.00   0.50    0.05    --   47.57 -19.00  30.00   80
 12  \w    -26.00  23.00   0.50    0.05    --   47.57 -19.00 -60.00   98
 13  \w    -18.00   8.00   0.50    0.05    --   47.57 -19.00-150.00   52
 14  \w     40.00  66.00   0.50    0.10    --  107.75 -77.00-180.00   52
 15  \w     77.00 102.00   0.50    0.10    --  107.75 -77.00-180.00   50
 16  \w     37.00  62.00   0.50    0.10    --  107.75 -57.00-150.00   50
 17  \w     38.00  63.00   0.50    0.10    --  107.75 -57.00 120.00   50
 18  \w   -100.00 -67.00   0.50    0.05    --  -47.57-148.00 167.00   66
 19  \w   -171.00 -86.00   0.50    0.10    -- -100.00 -57.00-120.00  170
 20  \w   -175.00-139.00   0.50    0.10    -- -100.00 -19.00 150.00   72
 21  \w   -118.00 -91.00   0.50    0.10    -- -100.00 -19.00 150.00   54
 22  \w    -68.00 -27.00   0.50    0.10    -- -100.00  57.00  90.00   82
 23  \w    -62.00 -37.00   0.50    0.10    -- -100.00  57.00  30.00   50
 24  \w   -112.00 -36.00   0.50    0.10    -- -100.00 125.00   0.00  152
 25  \w    -68.00 -43.00   0.50    0.10    -- -100.00 123.00  51.00   50
 26  \w    -94.00 -68.00   0.50    0.05    --  -47.57 123.00  51.00   52
 27  \w    -69.00 -44.00   0.50    0.10    -- -100.00  57.00-120.00   50
 28  \w   -109.00 -89.00   0.50    0.05    --  -47.57 148.00-143.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0277500000
_diffrn_orient_matrix_UB_12      -0.1338150000
_diffrn_orient_matrix_UB_13      0.0109624000
_diffrn_orient_matrix_UB_21      0.1304384000
_diffrn_orient_matrix_UB_22      -0.0284366000
_diffrn_orient_matrix_UB_23      0.0114890000
_diffrn_orient_matrix_UB_31      0.0009992000
_diffrn_orient_matrix_UB_32      0.0119878000
_diffrn_orient_matrix_UB_33      0.1490680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.988
_diffrn_reflns_theta_min         3.828
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0723P)^2^+0.5879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2391
_reflns_number_total             2659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04210j2.cif
_cod_data_source_block           tangshizhong3_0425_auto
_cod_database_code               7130711
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.802
_shelx_estimated_absorpt_t_min   0.615
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_shelx_res_checksum              69949
_shelx_hkl_checksum              36911
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.745
_oxdiff_exptl_absorpt_empirical_full_min 0.403