Electrochemically driven α-thiocarbamylation via a dehydrocoupling strategy of β-ketoesters with amines and CS2
Wang, Qian; Meng, Xiu-Jin; Tang, Hai-Tao; Pan, Ying-Ming; Duan, Wen-Gui; He, Mu-Xue; Green Chemistry 25 (2023) 2572–2576; doi:10.1039/D2GC04544C

data_7246419
_publ_section_title
;
 Electrochemically driven \a-thiocarbamylation via a dehydrocoupling
 strategy of \b-ketoesters with amines and CS2
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2572
_journal_page_last               2576
_journal_paper_doi               10.1039/D2GC04544C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H19 N O3 S2'
_chemical_formula_sum            'C16 H19 N O3 S2'
_chemical_formula_weight         337.44
_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     iterative
_audit_creation_date             2022-11-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-15 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.866(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6432(2)
_cell_length_b                   16.4149(2)
_cell_length_c                   9.6857(2)
_cell_measurement_reflns_used    18311
_cell_measurement_temperature    294.5(3)
_cell_measurement_theta_max      75.5050
_cell_measurement_theta_min      2.7430
_cell_volume                     1692.87(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.5(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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   -103.00 -25.00   0.50    0.50    --  -42.99 149.00-160.00  156
  2  \w   -116.00 -57.00   0.50    0.50    --  -42.99-149.00 152.00  118
  3  \w    -85.00 -11.00   0.50    0.50    --  -42.99 123.00  36.00  148
  4  \w     33.00  96.00   0.50    0.50    --   42.99-123.00 -44.00  126
  5  \w     49.00  94.00   0.50    0.50    --   42.99-149.00 152.00   90
  6  \w   -120.00 -81.00   0.50    1.00    --  -90.25-123.00 -44.00   78
  7  \w    -67.00 -42.00   0.50    1.00    --  -90.25 123.00  36.00   50
  8  \w    -64.00 -39.00   0.50    1.00    --  -90.25 149.00-160.00   50
  9  \w     99.00 124.00   0.50    1.00    --  109.26 149.00-160.00   50
 10  \w     71.00 110.00   0.50    1.00    --  109.26-123.00 -44.00   78
 11  \w     83.00 125.00   0.50    1.00    --  109.26-149.00 152.00   84
 12  \w     97.00 142.00   0.50    1.00    --  109.26 123.00  36.00   90
 13  \w    -42.00 -16.00   0.50    0.50    --  -42.99 125.00   0.00   52
 14  \w    -26.00  38.00   0.50    0.50    --  -42.99  19.00   0.00  128
 15  \w    -26.00  21.00   0.50    0.50    --  -42.99  19.00 -60.00   94
 16  \w    -27.00  36.00   0.50    0.50    --  -42.99  19.00  60.00  126
 17  \w    -36.00  16.00   0.50    0.50    --   42.99 -19.00-150.00  104
 18  \w     36.00  93.00   0.50    0.50    --   42.99-125.00-120.00  114
 19  \w    -51.00 -20.00   0.50    1.00    --  -90.25  45.00 -30.00   62
 20  \w    -81.00 -42.00   0.50    1.00    --  -90.25 -15.00 150.00   78
 21  \w   -165.00 -93.00   0.50    1.00    --  -90.25 -15.00 150.00  144
 22  \w   -162.00 -69.00   0.50    1.00    --  -90.25 -54.00  12.18  186
 23  \w   -127.00-102.00   0.50    1.00    --  -90.25-149.00 152.00   50
 24  \w    -45.00 -17.00   0.50    1.00    --  -90.25  45.00 150.00   56
 25  \w     72.00 103.00   0.50    1.00    --  109.26-125.00-180.00   62
 26  \w     96.00 123.00   0.50    1.00    --  109.26 125.00-180.00   54
 27  \w     43.00  69.00   0.50    1.00    --  109.26-125.00-180.00   52
 28  \w     38.00  70.00   0.50    1.00    --  109.26 -61.00 -60.00   64
 29  \w     49.00  75.00   0.50    1.00    --  109.26 -94.00   0.00   52
 30  \w     46.00  71.00   0.50    1.00    --  109.26 -61.00   0.00   50
 31  \w     36.00  70.00   0.50    1.00    --  109.26 -61.00 150.00   68
 32  \w     32.00 177.00   0.50    1.00    --  109.26   0.00  30.00  290
 33  \w    137.00 163.00   0.50    1.00    --  109.26 125.00   0.00   52
 34  \w     96.00 121.00   0.50    1.00    --  109.26 125.00   0.00   50
 35  \w     35.00  96.00   0.50    1.00    --  109.26 -77.00-150.00  122
 36  \w     36.00  71.00   0.50    1.00    --  109.26 -61.00 -90.00   70
 37  \w     80.00 105.00   0.50    1.00    --  109.26 -94.00   0.00   50
 38  \w     78.00 106.00   0.50    1.00    --  109.26 -99.00 156.87   56
 39  \w     35.00  71.00   0.50    1.00    --  109.26 -61.00 -30.00   72
 40  \w     35.00  60.00   0.50    1.00    --  109.26 -61.00-180.00   50
 41  \w    130.00 173.00   0.50    1.00    --  109.26 125.00-180.00   86
 42  \w     37.00  63.00   0.50    1.00    --  109.26-125.00 -60.00   52
 43  \w     80.00 105.00   0.50    1.00    --  109.26 -94.00 -30.00   50
 44  \w     70.00 105.00   0.50    1.00    --  109.26 -77.00 150.00   70
 45  \w     85.00 111.00   0.50    1.00    --  109.26-125.00   0.00   52
 46  \w     48.00  79.00   0.50    1.00    --  109.26-125.00   0.00   62
 47  \w     90.00 173.00   0.50    1.00    --  109.26  30.00  90.00  166
 48  \w    125.00 173.00   0.50    1.00    --  109.26  45.00-180.00   96
 49  \w     95.00 121.00   0.50    1.00    --  109.26-137.00 158.02   52
 50  \w     42.00  86.00   0.50    1.00    --  109.26-137.00 158.02   88
 51  \w     35.00  64.00   0.50    1.00    --  109.26 -77.00 150.00   58
 52  \w     36.00 110.00   0.50    1.00    --  109.26-121.00 -74.30  148
 53  \w     35.00  71.00   0.50    1.00    --  109.26 -61.00  90.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0096550000
_diffrn_orient_matrix_UB_12      0.0932337000
_diffrn_orient_matrix_UB_13      0.0096401000
_diffrn_orient_matrix_UB_21      -0.1441874000
_diffrn_orient_matrix_UB_22      -0.0066447000
_diffrn_orient_matrix_UB_23      -0.0634610000
_diffrn_orient_matrix_UB_31      0.0069430000
_diffrn_orient_matrix_UB_32      -0.0081693000
_diffrn_orient_matrix_UB_33      0.1616963000
_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  0.0979
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.424
_diffrn_reflns_theta_min         4.152
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1267P)^2^+1.1765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3274
_reflns_number_total             3473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04544c2.cif
_cod_data_source_block           20221104-pym-wq-201101_auto
_cod_depositor_comments          'Adding full bibliography for 7246419.cif.'
_cod_database_code               7246419
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N  O S'
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.757
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              62152
_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 2.301
_oxdiff_exptl_absorpt_empirical_full_min 0.456