Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyldiazenyl)aniline (aniline yellow) with <small>L</small>-tartaric acid
Smith, Graham; Wermuth, Urs D.; Young, David J.; Acta Crystallographica Section C 66 (2010) o345–o348; doi:10.1107/S0108270110020597

data_2017702
_publ_section_title
;
 Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded
 structure of the 1:1 proton-transfer salt of the diazo-dye precursor
 4-(phenyldiazenyl)aniline (aniline yellow) with
 <small>L</small>-tartaric acid
;
_journal_coeditor_code           FG3168
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o345
_journal_page_last               o348
_journal_paper_doi               10.1107/S0108270110020597
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H12 N3 + , C4 H5 O6 -'
_chemical_formula_moiety         'C12 H12 N3 + , C4 H5 O6 -'
_chemical_formula_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.33
_chemical_melting_point          467
_chemical_name_common
;
4-(phenyldiazenyl)anilinium hydrogen (2<i>R</i>,3<i>R</i>)-tartrate
;
_chemical_name_systematic
;
4-(phenyldiazenyl)anilinium
(2<i>R</i>,3<i>R</i>)-3-carboxy-2,3-dihydroxypropanoate
;
_space_group_IT_number           1
_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                91.754(3)
_cell_angle_beta                 91.308(3)
_cell_angle_gamma                108.135(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1710(3)
_cell_length_b                   7.4134(3)
_cell_length_c                   18.2438(6)
_cell_measurement_reflns_used    7191
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.15
_cell_measurement_theta_min      2.89
_cell_volume                     792.33(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Gemini-S CCD 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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16695
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0802P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3593
_reflns_number_total             4174
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3168.cif
_cod_data_source_block           I
_cod_database_code               2017702
_cod_database_fobs_code          2017702