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_7155275
_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 H15 N O2 S2'
_chemical_formula_sum            'C19 H15 N O2 S2'
_chemical_formula_weight         353.44
_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'
_audit_creation_date             2016-02-29
_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                 103.740(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.385(2)
_cell_length_b                   13.037(2)
_cell_length_c                   8.2869(14)
_cell_measurement_reflns_used    2115
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.97
_cell_volume                     1719.5(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)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.9844
_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  0.0607
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8283
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         23.53
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9242.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.3652
_exptl_crystal_description       plate
_exptl_crystal_F_000             736.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.3767
_refine_diff_density_min         -0.3779
_refine_diff_density_rms         0.0913
_refine_ls_d_res_high            0.8903
_refine_ls_d_res_low             7.9582
_refine_ls_goodness_of_fit_ref   1.0511
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0511
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0313P)^2^+0.4103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1906
_reflns_number_total             2559
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ob01856d2.cif
_cod_data_source_block           SK_01_489
_cod_depositor_comments
;Adding full bibliography for 7155275--7155277.cif.

 Adding full bibliography for 7155275--7155277.cif.
;
_cod_original_cell_volume        1719.6(5)
_cod_database_code               7155275
_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:
 C19(H19), C3(H3), C7(H7), C11(H11), C10(H10), C13(H13), C18(H18), C6(H6),
 C5(H5), C16(H16), C17(H17), C12(H12), C9(H9), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'