Nickel catalyzed site selective C-H functionalization of α-aryl-thioamides.
Bandyopadhyay, Debashruti; Thirupathi, Annaram; Dhage, Nagsen Munjaji; Mohanta, Nirmala; Peruncheralathan, S.; Organic & biomolecular chemistry 16 (2018) 6405–6409; doi:10.1039/c8ob01712c

data_7156388
_publ_section_title
;
 Nickel catalyzed site selective C-H functionalization of
 \a-aryl-thioamides.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6405
_journal_page_last               6409
_journal_paper_doi               10.1039/c8ob01712c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.38
_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_creation_date             2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.046(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7047(2)
_cell_length_b                   10.3186(2)
_cell_length_c                   13.6857(3)
_cell_measurement_reflns_used    10815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.1720
_cell_measurement_theta_min      4.0870
_cell_volume                     1520.99(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9756
_diffrn_measured_fraction_theta_max 0.9756
_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   -104.00 -48.00   0.50    0.25    --  -38.50-162.00 -24.00  112
  2  \w   -108.00 -22.00   0.50    0.25    --  -38.50 162.00   2.00  172
  3  \w    -84.00   5.00   0.50    0.25    --  -38.50 117.00-147.00  178
  4  \w     17.00  96.00   0.50    0.25    --   49.56-117.00 125.00  158
  5  \w     44.00 119.00   0.50    0.25    --   49.56-162.00 -24.00  150
  6  \w     69.00 115.00   0.50    0.25    --   49.56 162.00   2.00   92
  7  \w     44.00 142.00   0.50    1.00    --  102.63-162.00 -24.00  196
  8  \w     98.00 170.00   0.50    1.00    --  102.63 117.00-147.00  144
  9  \w     36.00 113.00   0.50    1.00    --  102.63-117.00 125.00  154
 10  \w     69.00 162.00   0.50    1.00    --  102.63 162.00   2.00  186
 11  \w    -62.00  26.00   0.50    0.25    --  -38.50  77.00-120.00  176
 12  \w    -17.00  53.00   0.50    0.25    --   49.56 -37.00 -90.00  140
 13  \w     38.00 107.00   0.50    1.00    --  102.63 -45.00 -90.00  138
 14  \w     40.00 116.00   0.50    1.00    --  102.63 -61.00 -90.00  152
 15  \w     40.00 116.00   0.50    1.00    --  102.63 -61.00  30.00  152
 16  \w     95.00 171.00   0.50    1.00    --  102.63  15.00  30.00  152
 17  \w     80.00 167.00   0.50    1.00    --  102.63  77.00 -90.00  174
 18  \w     38.00 107.00   0.50    1.00    --  102.63 -45.00   0.00  138
 19  \w     38.00 107.00   0.50    1.00    --  102.63 -45.00  90.00  138
 20  \w    109.00 160.00   0.50    1.00    --  102.63  45.00-150.00  102
 21  \w     99.00 167.00   0.50    1.00    --  102.63  45.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0586336000
_diffrn_orient_matrix_UB_12      0.0299292000
_diffrn_orient_matrix_UB_13      0.1197947000
_diffrn_orient_matrix_UB_21      -0.0844976000
_diffrn_orient_matrix_UB_22      0.1197429000
_diffrn_orient_matrix_UB_23      -0.0180078000
_diffrn_orient_matrix_UB_31      -0.0993503000
_diffrn_orient_matrix_UB_32      -0.0840419000
_diffrn_orient_matrix_UB_33      0.0170920000
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15328
_diffrn_reflns_theta_full        75.5125
_diffrn_reflns_theta_max         75.51
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3553
_exptl_crystal_description       needle
_exptl_crystal_F_000             651.2294
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2363
_refine_diff_density_min         -0.4255
_refine_diff_density_rms         0.0986
_refine_ls_d_res_high            0.7962
_refine_ls_d_res_low             10.7706
_refine_ls_goodness_of_fit_ref   1.0565
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0565
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0758P)^2^+0.3490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2834
_reflns_number_total             3077
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob01712c2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7156387--7156388.cif.'
_cod_database_code               7156388
_chemical_oxdiff_formula         'C72 H56 N4 O8 S4 '
_reflns_odcompleteness_completeness 99.79
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H10), C6(H6), C7(H7), C10(H12), C14(H16), C11(H13), C12(H14), C13(H15)
2.b Idealised Me refined as rotating group:
 C17(H20a,H20b,H20c), C16(H18a,H18b,H18c)
;
_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 2.461
_oxdiff_exptl_absorpt_empirical_full_min 0.474