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_2017342
_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 H11 N3, 2C7 H4 N2 O6'
_chemical_formula_moiety         'C12 H11 N3, 2(C7 H4 N2 O6)'
_chemical_formula_sum            'C26 H19 N7 O12'
_chemical_formula_weight         621.48
_chemical_melting_point          453
_chemical_name_systematic
;
4-(phenyldiazenyl)aniline--3,5-dinitrobenzoic acid (1/2)
;
_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                112.292(8)
_cell_angle_beta                 92.560(7)
_cell_angle_gamma                114.072(8)
_cell_formula_units_Z            1
_cell_length_a                   8.2048(7)
_cell_length_b                   8.8859(7)
_cell_length_c                   11.5802(9)
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      2.89
_cell_volume                     693.09(13)
_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
;
SHELXS97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8021
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0446P)^2^+0.0825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                1989
_reflns_number_total             2440
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3306.cif
_cod_data_source_block           III
_cod_database_code               2017342
_cod_database_fobs_code          2017342