Facile Synthesis of 1,2-Thiobenzonitriles via Cu-Catalyzed Denitrogenative Radical Coupling Reaction
Zhou, Yao; Wang, Ya; Lou, Yixian; Song, Qiuling; Chemical Communications  (2019) –; doi:10.1039/C9CC05099J

data_7123934
_publ_section_title
;
 Facile Synthesis of 1,2-Thiobenzonitriles via Cu-Catalyzed
 Denitrogenative Radical Coupling Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05099J
_journal_year                    2019
_chemical_formula_moiety         'C14 H9 N O S'
_chemical_formula_sum            'C14 H9 N O S'
_chemical_formula_weight         239.30
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20jwyd
_audit_creation_date             2018-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-07-27 deposited with the CCDC.    2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.535(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2127(8)
_cell_length_b                   13.0460(12)
_cell_length_c                   11.9273(15)
_cell_measurement_reflns_used    986
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.5530
_cell_measurement_theta_min      4.2390
_cell_volume                     1106.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_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     -3.00  82.00   1.00   22.50    --   15.49  38.00 -90.00   85
  2  \w    -17.00  10.00   1.00   22.50    --  -16.12 -99.00-120.00   27
  3  \w    -52.00 -26.00   1.00   22.50    --   15.49 -77.00 120.00   26
  4  \w     16.00  41.00   1.00   22.50    --   15.49 -77.00 120.00   25
  5  \w     35.00  86.00   1.00   22.50    --   15.49 178.00-120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0019455000
_diffrn_orient_matrix_UB_12      -0.0519728000
_diffrn_orient_matrix_UB_13      0.0173787000
_diffrn_orient_matrix_UB_21      -0.0200486000
_diffrn_orient_matrix_UB_22      -0.0154996000
_diffrn_orient_matrix_UB_23      -0.0576776000
_diffrn_orient_matrix_UB_31      0.0976904000
_diffrn_orient_matrix_UB_32      -0.0042613000
_diffrn_orient_matrix_UB_33      -0.0012766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5124
_diffrn_reflns_theta_full        24.9981
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.4360
_exptl_crystal_description       block
_exptl_crystal_F_000             496.6926
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.58
_refine_diff_density_max         0.3869
_refine_diff_density_min         -0.3713
_refine_diff_density_rms         0.0928
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7045
_refine_ls_goodness_of_fit_ref   0.8443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8443
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1309
_reflns_number_total             1945
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc05099j2.cif
_cod_data_source_block           exp_5832
_cod_database_code               7123934
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00A(H00A), C009(H009), C00B(H00B), C008(H008)
2.b Idealised Me refined as rotating group:
 C00H(H00c,H00f,H00g)
;
_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.724