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_7130710
_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         'C13 H21 N S'
_chemical_formula_sum            'C13 H21 N S'
_chemical_formula_weight         223.37
_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                 94.9987(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.16255(17)
_cell_length_b                   10.98512(17)
_cell_length_c                   10.23216(13)
_cell_measurement_reflns_used    7016
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3990
_cell_measurement_theta_min      3.9590
_cell_volume                     1249.92(3)
_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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_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     61.00 105.00   0.50    0.05    --   47.57 147.00 -11.00   88
  2  \w     90.00 115.00   0.50    0.08    --  107.75 147.00 -11.00   50
  3  \w     79.00 142.00   0.50    0.08    --  107.75 124.00-177.00  126
  4  \w    131.00 174.00   0.50    0.08    --  107.75  19.00   0.00   86
  5  \w     95.00 121.00   0.50    0.08    --  107.75  19.00   0.00   52
  6  \w     46.00  72.00   0.50    0.08    --  107.75 -99.00 120.00   52
  7  \w     74.00 108.00   0.50    0.08    --  107.75-124.00 103.00   68
  8  \w     35.00  62.00   0.50    0.08    --  107.75 -57.00  60.00   54
  9  \w     67.00 120.00   0.50    0.08    --  107.75-147.00 -61.00  106
 10  \w     67.00 103.00   0.50    0.08    --  107.75 -77.00 -60.00   72
 11  \w     38.00  63.00   0.50    0.08    --  107.75 -57.00-120.00   50
 12  \w     46.00  72.00   0.50    0.08    --  107.75 -77.00-180.00   52
 13  \w    -23.00  23.00   0.50    0.05    --   47.57 -19.00-150.00   92
 14  \w    -26.00  22.00   0.50    0.05    --   47.57 -19.00  90.00   96
 15  \w    -26.00  26.00   0.50    0.05    --  -47.57  19.00 -60.00  104
 16  \w    -93.00 -44.00   0.50    0.05    --  -47.57 124.00-177.00   98
 17  \w    -97.00 -70.00   0.50    0.05    --  -47.57 147.00 -11.00   54
 18  \w   -105.00 -79.00   0.50    0.08    -- -100.00 147.00 -11.00   52
 19  \w   -122.00 -65.00   0.50    0.08    -- -100.00 140.00  85.57  114
 20  \w   -112.00 -46.00   0.50    0.08    -- -100.00 125.00 120.00  132
 21  \w    -64.00 -27.00   0.50    0.08    -- -100.00  57.00 -30.00   74
 22  \w   -172.00 -85.00   0.50    0.08    -- -100.00 -57.00 150.00  174
 23  \w   -115.00 -80.00   0.50    0.08    -- -100.00 -77.00 120.00   70
 24  \w   -172.00-126.00   0.50    0.08    -- -100.00 -77.00 120.00   92
 25  \w   -118.00 -89.00   0.50    0.05    --  -47.57-147.00 -61.00   58
;
_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      -0.0835033000
_diffrn_orient_matrix_UB_12      0.1118992000
_diffrn_orient_matrix_UB_13      -0.0089097000
_diffrn_orient_matrix_UB_21      -0.1097285000
_diffrn_orient_matrix_UB_22      -0.0837289000
_diffrn_orient_matrix_UB_23      0.0085979000
_diffrn_orient_matrix_UB_31      0.0134444000
_diffrn_orient_matrix_UB_32      0.0114650000
_diffrn_orient_matrix_UB_33      0.1506373000
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_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       -10
_diffrn_reflns_number            8622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.566
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48240
_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    1.187
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0752P)^2^+0.9405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2346
_reflns_number_total             2508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04210j2.cif
_cod_data_source_block           tangshizhong2_0425_auto
_cod_database_code               7130710
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_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), C5(H5), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_shelx_res_checksum              37688
_shelx_hkl_checksum              26733
_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 2.678
_oxdiff_exptl_absorpt_empirical_full_min 0.473