Synthesis and crystal structure of (<i>E</i>)-1,2-bis[2-(methylsulfanyl)phenyl]diazene
Hoffmann, Jonas; Kuczmera, Thomas J.; Lork, Enno; Staubitz, Anne; Acta Crystallographica Section E 75 (2019) 1808–1811; doi:10.1107/S2056989019014592

data_2243161
_publ_section_title
;
 Synthesis and crystal structure of
 (<i>E</i>)-1,2-bis[2-(methylsulfanyl)phenyl]diazene
;
_journal_coeditor_code           WM5522
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1808
_journal_page_last               1811
_journal_paper_doi               10.1107/S2056989019014592
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H14 N2 S2'
_chemical_formula_moiety         'C14 H14 N2 S2'
_chemical_formula_sum            'C14 H14 N2 S2'
_chemical_formula_weight         274.39
_chemical_name_systematic
;
(<i>E</i>)-1,2-Bis[2-(methylsulfanyl)phenyl]diazene
;
_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
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0656(5)
_cell_length_b                   12.1787(4)
_cell_length_c                   8.3471(3)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.29
_cell_volume                     1320.55(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         2.292
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.377
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0401P)^2^+0.6716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2842
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5522sup1.cif
_cod_data_source_block           I
_cod_database_code               2243161
_cod_database_fobs_code          2243161
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.937