Proton transfer <i>versus</i> nontransfer in compounds of the diazo-dye precursor 4-(phenyldiazenyl)aniline (aniline yellow) with strong organic acids: the 5-sulfosalicylate and the dichroic benzenesulfonate salts, and the 1:2 adduct with 3,5-dinitrobenzoic acid
Smith, Graham; Wermuth, Urs D.; Young, David J.; White, Jonathan M.; Acta Crystallographica Section C 65 (2009) o543–o548; doi:10.1107/S0108270109036622

data_2017341
_publ_section_title
;
 Proton transfer <i>versus</i> nontransfer in compounds of the
 diazo-dye precursor 4-(phenyldiazenyl)aniline (aniline yellow) with
 strong organic acids: the 5-sulfosalicylate and the dichroic
 benzenesulfonate salts, and the 1:2 adduct with 3,5-dinitrobenzoic
 acid
;
_journal_coeditor_code           GD3306
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o543
_journal_page_last               o548
_journal_paper_doi               10.1107/S0108270109036622
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C12 H12 N3 +, 2C6 H5 O3 S -'
_chemical_formula_moiety         '2(C12 H12 N3 +), 2(C6 H5 O3 S -)'
_chemical_formula_sum            'C36 H34 N6 O6 S2'
_chemical_formula_weight         710.82
_chemical_melting_point_gt       533
_chemical_name_common            '4-phenylazoanilinium benzenesulfonate'
_chemical_name_systematic
;
2-(4-aminophenyl)-1-phenylhydrazin-1-ium (4-phenyldiazenyl)anilinium
bis(benzenesulfonate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                77.937(5)
_cell_angle_beta                 83.985(5)
_cell_angle_gamma                86.971(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7601(4)
_cell_length_b                   13.0794(8)
_cell_length_c                   23.6556(15)
_cell_measurement_reflns_used    9206
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.82
_cell_measurement_theta_min      3.12
_cell_volume                     1732.4(2)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini-S CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22657
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red-black
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.1286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                5717
_reflns_number_total             7187
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3306.cif
_cod_data_source_block           II
_cod_database_code               2017341
_cod_database_fobs_code          2017341