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_2017340
_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          'C12 H12 N3 +, C7 H5 O6 S -, C H4 O'
_chemical_formula_moiety         'C12 H12 N3 +, C7 H5 O6 S -, C H4 O'
_chemical_formula_sum            'C20 H21 N3 O7 S'
_chemical_formula_weight         447.46
_chemical_melting_point_gt       485
_chemical_melting_point_lt       488
_chemical_name_systematic
;
2-(4-aminophenyl)-1-phenylhydrazin-1-ium
3-carboxy-4-hydroxybenzenesulfonate methanol solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.145(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7174(7)
_cell_length_b                   20.1160(16)
_cell_length_c                   11.8827(9)
_cell_measurement_reflns_used    3449
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.35
_cell_volume                     2067.6(3)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10840
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red-black
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.4842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                3102
_reflns_number_total             3640
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3306.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017340
_cod_database_fobs_code          2017340