Regioselective transition metal- and halogen-free direct dithiolation at C(sp(3))-H of nitrotoluenes with diaryl disulfides.
Kumar, Shailesh; Kadu, Rahul; Kumar, Sangit; Organic & biomolecular chemistry 14 (2016) 9210–9214; doi:10.1039/c6ob01856d

data_7155276
_publ_section_title
;
 Regioselective transition metal- and halogen-free direct dithiolation at
 C(sp(3))-H of nitrotoluenes with diaryl disulfides.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9210
_journal_page_last               9214
_journal_paper_doi               10.1039/c6ob01856d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C19 H13 Br2 N O2 S2'
_chemical_formula_sum            'C19 H13 Br2 N O2 S2'
_chemical_formula_weight         511.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_primary     iterative
_audit_creation_date             2016-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-06-28 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.845(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6546(8)
_cell_length_b                   29.982(3)
_cell_length_c                   8.7107(10)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.56
_cell_volume                     1891.9(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      187.23
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4339
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.519
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.6958.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.7948
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.6281
_refine_diff_density_min         -0.5255
_refine_diff_density_rms         0.1338
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             7.9488
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0694
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0694
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0167P)^2^+2.5101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0603
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -9
_reflns_limit_k_max              38
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -5
_reflns_number_gt                3710
_reflns_number_total             4339
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ob01856d2.cif
_cod_data_source_block           SK_543_P
_cod_depositor_comments
;Adding full bibliography for 7155275--7155277.cif.

 Adding full bibliography for 7155275--7155277.cif.
;
_cod_original_cell_volume        1892.0(4)
_cod_database_code               7155276
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C15(H15), C18(H18), C12(H12), C7(H7), C9(H9), C6(H6),
 C19(H19), C4(H4), C3(H3), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'