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_4030011
_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         'C15 H9 N O S2'
_chemical_formula_sum            'C15 H9 N O S2'
_chemical_formula_weight         283.35
_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
_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                 99.044(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5913(7)
_cell_length_b                   14.7571(10)
_cell_length_c                   8.3539(5)
_cell_measurement_reflns_used    5185
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.39
_cell_volume                     1289.46(14)
_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      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.027
_diffrn_reflns_theta_min         1.947
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0481P)^2^+0.3306P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2088
_reflns_number_total             3024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501793q_si_003.cif
_cod_data_source_block           7g
_cod_depositor_comments
'Adding full bibliography for 4030011--4030013.cif.'
_cod_database_code               4030011
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.889
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15),
 C17(H17)
;
_shelx_res_checksum              30037
_shelx_hkl_checksum              77780