#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017342.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017342
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
'White, Jonathan M.'
_publ_section_title
;
 Proton transfer versus 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       ω
_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/[σ²(Fo²)+(0.0446P)²+0.0825P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            gd3306.cif
_cod_data_source_block           III
_cod_database_code               2017342
_cod_database_fobs_code          2017342
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1A 0.55044(15) 2.00276(15) 0.46048(10) 0.0365(3) Uani . . 1.000
N N4A 0.5346(4) 1.3392(4) 0.1456(3) 0.0522(10) Uani . . 0.500
C C1A 0.54603(17) 1.83104(18) 0.38400(13) 0.0344(4) Uani . . 1.000
C C2A 0.46975(18) 1.67703(18) 0.40837(13) 0.0381(5) Uani . . 1.000
C C3A 0.46505(19) 1.51471(19) 0.32679(14) 0.0424(5) Uani . . 1.000
C C4A 0.53747(19) 1.5009(2) 0.21861(15) 0.0438(5) Uani . . 1.000
C C5A 0.6170(2) 1.6555(2) 0.19546(14) 0.0454(5) Uani . . 1.000
C C6A 0.62273(18) 1.81963(19) 0.27822(14) 0.0408(5) Uani . . 1.000
O O11 -0.06079(15) 0.12182(14) 0.14147(10) 0.0468(4) Uani . . 1.000
O O12 0.08141(14) 0.20224(12) -0.00162(9) 0.0411(3) Uani . . 1.000
O O31 0.32547(15) 0.84705(14) 0.07643(10) 0.0491(4) Uani . . 1.000
O O32 0.29333(17) 1.04248(14) 0.24268(11) 0.0621(4) Uani . . 1.000
O O51 -0.04017(17) 0.84183(14) 0.53163(11) 0.0621(4) Uani . . 1.000
O O52 -0.16179(15) 0.55597(15) 0.49171(10) 0.0521(4) Uani . . 1.000
N N3 0.26847(16) 0.88755(15) 0.17407(11) 0.0389(4) Uani . . 1.000
N N5 -0.07430(16) 0.68298(16) 0.46627(11) 0.0379(4) Uani . . 1.000
C C1 0.04311(17) 0.42637(16) 0.17231(11) 0.0302(4) Uani . . 1.000
C C2 0.14076(17) 0.56494(17) 0.13703(12) 0.0303(4) Uani . . 1.000
C C3 0.16234(17) 0.73976(16) 0.21019(12) 0.0302(4) Uani . . 1.000
C C4 0.09292(17) 0.78354(17) 0.31756(12) 0.0314(4) Uani . . 1.000
C C5 -0.00239(17) 0.64194(17) 0.34949(12) 0.0309(4) Uani . . 1.000
C C6 -0.03051(17) 0.46434(17) 0.27937(12) 0.0311(4) Uani . . 1.000
C C11 0.02321(18) 0.23897(18) 0.09566(13) 0.0333(4) Uani . . 1.000
H H2A 0.42170 1.68440 0.48040 0.0460 Uiso calc R 1.000
H H3A 0.41310 1.41310 0.34390 0.0510 Uiso calc R 1.000
H H4A 0.53290 1.39060 0.16290 0.0530 Uiso . . 0.500
H H5A 0.66650 1.64850 0.12400 0.0540 Uiso calc R 1.000
H H6A 0.67820 1.92250 0.26290 0.0490 Uiso calc R 1.000
H H41A 0.572(5) 1.324(5) 0.078(4) 0.074(13) Uiso . . 0.500
H H42A 0.481(5) 1.264(5) 0.163(4) 0.067(14) Uiso . . 0.500
H H2 0.19080 0.54090 0.06570 0.0360 Uiso calc R 1.000
H H4 0.10930 0.90170 0.36580 0.0380 Uiso calc R 1.000
H H6 -0.09720 0.37240 0.30340 0.0370 Uiso calc R 1.000
H H11 -0.074(3) 0.010(3) 0.0908(18) 0.078(6) Uiso . . 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O11 H11 . . . 111.2(15) no
N1A N1A C1A 2_696 . . 114.21(13) no
H41A N4A H42A . . . 124(5) no
C4A N4A H41A . . . 120(3) no
H4A N4A H42A . . . 120.00 no
C4A N4A H42A . . . 114(3) no
H4A N4A H41A . . . 113.00 no
O32 N3 C3 . . . 118.15(12) no
O31 N3 C3 . . . 117.83(12) no
O31 N3 O32 . . . 124.02(14) no
O51 N5 O52 . . . 124.44(13) no
O52 N5 C5 . . . 117.62(13) no
O51 N5 C5 . . . 117.94(13) no
C2A C1A C6A . . . 119.01(14) no
N1A C1A C6A . . . 116.52(14) no
N1A C1A C2A . . . 124.48(13) no
C1A C2A C3A . . . 120.63(14) no
C2A C3A C4A . . . 120.66(16) no
N4A C4A C3A . . . 117.4(2) no
N4A C4A C5A . . . 123.7(2) no
C3A C4A C5A . . . 118.81(15) no
C4A C5A C6A . . . 120.53(15) no
C1A C6A C5A . . . 120.32(15) no
C3A C2A H2A . . . 120.00 no
C1A C2A H2A . . . 120.00 no
C4A C3A H3A . . . 120.00 no
C2A C3A H3A . . . 120.00 no
C3A C4A H4A . . . 121.00 no
C5A C4A H4A . . . 121.00 no
C4A C5A H5A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C1A C6A H6A . . . 120.00 no
C5A C6A H6A . . . 120.00 no
C2 C1 C11 . . . 119.02(12) no
C6 C1 C11 . . . 121.01(13) no
C2 C1 C6 . . . 119.95(13) no
C1 C2 C3 . . . 118.83(12) no
N3 C3 C2 . . . 118.87(12) no
C2 C3 C4 . . . 123.08(13) no
N3 C3 C4 . . . 118.03(12) no
C3 C4 C5 . . . 116.16(13) no
N5 C5 C6 . . . 118.26(13) no
C4 C5 C6 . . . 123.42(13) no
N5 C5 C4 . . . 118.30(13) no
C1 C6 C5 . . . 118.56(13) no
O11 C11 C1 . . . 114.17(12) no
O12 C11 C1 . . . 121.55(14) no
O11 C11 O12 . . . 124.28(14) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 121.00 no
C3 C4 H4 . . . 122.00 no
C5 C4 H4 . . . 122.00 no
C1 C6 H6 . . . 121.00 no
C5 C6 H6 . . . 121.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C11 . . 1.306(2) no
O12 C11 . . 1.2247(18) no
O31 N3 . . 1.2258(17) no
O32 N3 . . 1.2226(18) no
O51 N5 . . 1.2214(18) no
O52 N5 . . 1.2190(19) no
O11 H11 . . 0.90(2) no
N1A C1A . . 1.429(2) no
N1A N1A . 2_696 1.2625(17) no
N4A C4A . . 1.352(4) no
N4A H41A . . 0.84(4) no
N4A H42A . . 0.74(5) no
N3 C3 . . 1.475(2) no
N5 C5 . . 1.4774(18) no
C1A C2A . . 1.398(2) no
C1A C6A . . 1.391(2) no
C2A C3A . . 1.376(2) no
C3A C4A . . 1.395(2) no
C4A C5A . . 1.396(3) no
C5A C6A . . 1.388(2) no
C2A H2A . . 0.9300 no
C3A H3A . . 0.9300 no
C4A H4A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
C1 C6 . . 1.3898(19) no
C1 C11 . . 1.494(2) no
C1 C2 . . 1.390(2) no
C2 C3 . . 1.388(2) no
C3 C4 . . 1.3780(19) no
C4 C5 . . 1.381(2) no
C5 C6 . . 1.385(2) no
C2 H2 . . 0.9300 no
C4 H4 . . 0.9300 no
C6 H6 . . 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O11 H11 O12 2_555 0.90(2) 1.75(2) 2.6426(16) 175(2) yes
N4A H41A O31 2_675 0.84(4) 2.31(4) 3.042(4) 147(4) yes
N4A H42A O32 . 0.74(5) 2.48(4) 3.213(4) 173(4) yes
C2A H2A O52 2_576 0.93 2.47 3.134(2) 129 no
C4 H4 O51 2_576 0.93 2.45 3.339(2) 161 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1A N1A C1A C2A 2_696 . . . -12.6(2) no
N1A N1A C1A C6A 2_696 . . . 167.00(13) no
C1A N1A N1A C1A . . 2_696 2_696 -180.00(12) no
O31 N3 C3 C2 . . . . 3.6(2) no
O31 N3 C3 C4 . . . . -177.94(14) no
O32 N3 C3 C2 . . . . -176.79(14) no
O32 N3 C3 C4 . . . . 1.6(2) no
O52 N5 C5 C4 . . . . 178.35(14) no
O52 N5 C5 C6 . . . . -3.1(2) no
O51 N5 C5 C6 . . . . 175.97(14) no
O51 N5 C5 C4 . . . . -2.6(2) no
N1A C1A C2A C3A . . . . 177.48(14) no
C6A C1A C2A C3A . . . . -2.1(2) no
C2A C1A C6A C5A . . . . 2.5(2) no
N1A C1A C6A C5A . . . . -177.13(14) no
C1A C2A C3A C4A . . . . 0.5(2) no
C2A C3A C4A N4A . . . . 177.5(2) no
C2A C3A C4A C5A . . . . 0.8(2) no
C3A C4A C5A C6A . . . . -0.4(2) no
N4A C4A C5A C6A . . . . -176.8(2) no
C4A C5A C6A C1A . . . . -1.2(2) no
C6 C1 C2 C3 . . . . -0.1(2) no
C11 C1 C2 C3 . . . . -178.60(13) no
C2 C1 C6 C5 . . . . -0.7(2) no
C11 C1 C6 C5 . . . . 177.76(13) no
C2 C1 C11 O11 . . . . 175.89(13) no
C2 C1 C11 O12 . . . . -4.4(2) no
C6 C1 C11 O11 . . . . -2.6(2) no
C6 C1 C11 O12 . . . . 177.18(14) no
C1 C2 C3 N3 . . . . 179.03(13) no
C1 C2 C3 C4 . . . . 0.7(2) no
N3 C3 C4 C5 . . . . -178.73(13) no
C2 C3 C4 C5 . . . . -0.4(2) no
C3 C4 C5 N5 . . . . 177.99(13) no
C3 C4 C5 C6 . . . . -0.5(2) no
N5 C5 C6 C1 . . . . -177.47(13) no
C4 C5 C6 C1 . . . . 1.0(2) no
