The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids
Smith, Graham; Wermuth, Urs D.; Young, David J.; White, Jonathan M.; Acta Crystallographica Section C 64 (2008) o123–o127; doi:10.1107/S0108270108001595

data_2016498
_publ_section_title
;
 The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline
 (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and
 5-nitroisophthalic acids
;
_journal_coeditor_code           GZ3114
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o123
_journal_page_last               o127
_journal_paper_doi               10.1107/S0108270108001595
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H12 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_moiety         'C12 H12 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_sum            'C20 H18 N4 O7'
_chemical_formula_weight         426.38
_chemical_melting_point          393
_chemical_name_common
'4-(phenylazo)anilinium hydrogen 5-nitroisophthalate monohydrate'
_chemical_name_systematic
;
4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 (Sheldrick, 2008)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0965(15)
_cell_length_b                   6.7602(7)
_cell_length_c                   43.091(5)
_cell_measurement_reflns_used    3315
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.38
_cell_volume                     4106.4(8)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            20144
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0846
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0P)^2^+14.8749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                2720
_reflns_number_total             3612
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gz3114.cif
_cod_data_source_block           III
_cod_database_code               2016498
_cod_database_fobs_code          2016498