Synthesis and crystal structure of (<i>E</i>)-2-({2-[azaniumylidene(methylsulfanyl)methyl]hydrazinylidene}methyl)benzene-1,4-diol hydrogen sulfate
Nehar, Oussama; Louhibi, Samira; Roisnel, Thierry; Acta Crystallographica Section E 75 (2019) 1738–1740; doi:10.1107/S2056989019014233

data_2243167
_publ_section_title
;
 Synthesis and crystal structure of
 (<i>E</i>)-2-({2-[azaniumylidene(methylsulfanyl)methyl]hydrazinylidene}methyl)benzene-1,4-diol
 hydrogen sulfate
;
_journal_coeditor_code           LH5926
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1738
_journal_page_last               1740
_journal_paper_doi               10.1107/S2056989019014233
_journal_volume                  75
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_iupac          'C9 H12 N3 O2 S +, H S O4 -'
_chemical_formula_moiety         'C9 H12 N3 O2 S +, H O4 S -'
_chemical_formula_sum            'C9 H13 N3 O6 S2'
_chemical_formula_weight         323.34
_chemical_name_systematic
;
(<i>E</i>)-2-({2-[Azaniumylidene(methylsulfanyl)methyl]hydrazinylidene}\
methyl)benzene-1,4-diol sulfate
;
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.440(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9411(8)
_cell_length_b                   16.139(2)
_cell_length_c                   16.426(3)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.9884
_cell_measurement_theta_min      2.5241
_cell_volume                     1288.2(4)
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.253
_diffrn_reflns_theta_min         3.569
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                2014
_reflns_number_total             2846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lh5926sup1.cif
_cod_data_source_block           global
_cod_original_cell_volume        1288.2(3)
_cod_database_code               2243167
_shelx_hkl_file                  {a6986d5e-fe3e-4309-af82-6f5f253b7b8a}
_shelx_hkl_checksum              68398
_shelx_res_file                  {fb63088b-adc4-496e-b539-a7298bb76c23}
_shelx_res_checksum              18719