Regioselective thiolation of arenes and heteroarenes: C-h functionalization strategy for C-s bond formation.
Varun, Begur Vasanthkumar; Prabhu, Kandikere Ramaiah; The Journal of organic chemistry 79 (2014) 9655–9668; doi:10.1021/jo501793q

data_4030012
_publ_section_title
;
 Regioselective thiolation of arenes and heteroarenes: C-h
 functionalization strategy for C-s bond formation.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9655
_journal_page_last               9668
_journal_paper_doi               10.1021/jo501793q
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C12 H9 N O S2'
_chemical_formula_sum            'C12 H9 N O S2'
_chemical_formula_weight         247.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.807(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.601(2)
_cell_length_b                   9.794(2)
_cell_length_c                   13.733(3)
_cell_measurement_reflns_used    4790
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      3.21
_cell_volume                     1118.4(4)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8714
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.439
_diffrn_reflns_theta_min         2.536
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0852 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.9154.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0567
_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^)+(0.1090P)^2^+0.7067P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1947
_reflns_number_total             2346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501793q_si_002.cif
_cod_data_source_block           7a
_cod_depositor_comments
'Adding full bibliography for 4030011--4030013.cif.'
_cod_original_cell_volume        1118.5(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4030012
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.896
_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:
 C1(H1), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              82931
_shelx_hkl_checksum              45842