Copper-Catalyzed Cyanothiolation to Incorporate Sulfur-Substituted Quaternary Carbon Center
Jiang, Huanfeng; Huang, Yubing; Li, Xianwei; Wang, Xu; Yu, Yue; Zheng, Jia; Wu, Wanqing; Chem. Sci.  (2017) –; doi:10.1039/C7SC02867A

data_1546783
_publ_section_title
;
 Copper-Catalyzed Cyanothiolation to Incorporate Sulfur-Substituted
 Quaternary Carbon Center
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02867A
_journal_year                    2017
_chemical_formula_moiety         'C20 H17 N S'
_chemical_formula_sum            'C20 H17 N O0 S'
_chemical_formula_weight         303.41
_chemical_name_systematic
;
 ? 
;
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1nwzgz
_audit_creation_date             2016-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2017-04-26 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8227(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.18234(17)
_cell_length_b                   5.96601(10)
_cell_length_c                   23.6894(4)
_cell_measurement_reflns_used    4134
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7230
_cell_measurement_theta_min      5.2090
_cell_volume                     1574.82(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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    -66.00  31.00   1.00    1.00    --  -41.89  37.00-120.00   97
  2  \w      1.00  79.00   1.00    1.00    --   41.89 -99.00 -30.00   78
  3  \w     32.00  97.00   1.00    1.00    --   41.89-125.00-150.00   65
  4  \w     25.00  82.00   1.00    1.00    --  107.79 -94.00   0.00   57
  5  \w     67.00 133.00   1.00    1.00    --  107.79 -61.00  30.00   66
  6  \w    109.00 144.00   1.00    1.00    --  107.79  30.00 120.00   35
  7  \w    100.00 138.00   1.00    1.00    --  107.79  89.00 120.00   38
  8  \w    103.00 177.00   1.00    1.00    --  107.79 125.00  60.00   74
  9  \w     89.00 172.00   1.00    1.00    --  107.79  45.00-120.00   83
 10  \w    116.00 176.00   1.00    1.00    --  107.79 125.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1076045000
_diffrn_orient_matrix_UB_12      0.1056149000
_diffrn_orient_matrix_UB_13      -0.0352736000
_diffrn_orient_matrix_UB_21      0.0761628000
_diffrn_orient_matrix_UB_22      0.2087512000
_diffrn_orient_matrix_UB_23      -0.0103477000
_diffrn_orient_matrix_UB_31      0.0417751000
_diffrn_orient_matrix_UB_32      -0.1092637000
_diffrn_orient_matrix_UB_33      -0.0539083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5794
_diffrn_reflns_theta_full        73.88
_diffrn_reflns_theta_max         73.88
_diffrn_reflns_theta_min         3.75
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.3175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                2892
_reflns_number_total             3098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc02867a2.cif
_cod_data_source_block           1609235
_cod_database_code               1546783
_chemical_oxdiff_formula         'C20 H20 N4 O4'
_chemical_oxdiff_usercomment     HYB-15a
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C16(H16), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C)
;
_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 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.637