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_7156387
_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         310.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4456(3)
_cell_length_b                   9.07642(17)
_cell_length_c                   22.7259(5)
_cell_measurement_reflns_used    6710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3650
_cell_measurement_theta_min      3.8480
_cell_volume                     2979.69(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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    -56.00 -30.00   0.50    2.60    --  -38.50 126.00  35.00   52
  2  \w    -70.00 -44.00   0.50    2.60    --  -38.50 144.00-156.00   52
  3  \w     49.00  74.00   0.50    2.60    --   49.31-144.00 150.00   50
  4  \w     26.00  98.00   0.50    2.60    --   49.31-126.00 -41.00  144
  5  \w     72.00 117.00   0.50   11.00    --  106.38-126.00 -41.00   90
  6  \w     84.00 169.00   0.50   11.00    --  106.38 144.00-156.00  170
  7  \w    108.00 133.00   0.50   11.00    --  106.38 126.00  35.00   50
  8  \w   -100.00 -36.00   0.50    2.60    --  -38.50 -37.00 150.00  128
  9  \w     38.00 108.00   0.50    2.60    --   49.31  57.00  30.00  140
 10  \w     54.00  82.00   0.50    2.60    --   49.31  37.00 -60.00   56
 11  \w     94.00 120.00   0.50   11.00    --  106.38 -61.00 -60.00   52
 12  \w     46.00  73.00   0.50   11.00    --  106.38 -61.00 -60.00   54
 13  \w     97.00 171.00   0.50   11.00    --  106.38 125.00 120.00  148
 14  \w     48.00  83.00   0.50   11.00    --  106.38 -30.00  90.00   70
 15  \w     39.00 104.00   0.50   11.00    --  106.38 -30.00-120.00  130
 16  \w    103.00 154.00   0.50   11.00    --  106.38  45.00 120.00  102
;
_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      -0.0045725000
_diffrn_orient_matrix_UB_12      -0.0092635000
_diffrn_orient_matrix_UB_13      0.0676314000
_diffrn_orient_matrix_UB_21      -0.0980376000
_diffrn_orient_matrix_UB_22      0.0666460000
_diffrn_orient_matrix_UB_23      -0.0012414000
_diffrn_orient_matrix_UB_31      -0.0416631000
_diffrn_orient_matrix_UB_32      -0.1558523000
_diffrn_orient_matrix_UB_33      -0.0045328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12918
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.515
_diffrn_reflns_theta_min         3.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (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    1.384
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0930
_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^)+(0.0655P)^2^+9.6138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2459
_reflns_number_total             3069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01712c2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7156387--7156388.cif.'
_cod_database_code               7156387
_chemical_oxdiff_formula         'C128 H112 N24 O16 S8 '
_diffrn_oxdiff_ac3_digest_frames
;
017c25b96c53316d8de0487ea1f250373400027ce8b
;
_diffrn_oxdiff_ac3_digest_hkl
;
01f1b8e0b9847f2d838da8d74f4d0125d12c62
;
_reflns_odcompleteness_completeness 99.64
_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(H1), C4(H4), C7(H7), C17(H17), C13(H13), C16(H16), C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              7062
_shelx_shelxl_version_number     2016/4
_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 2.741
_oxdiff_exptl_absorpt_empirical_full_min 0.142