#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229647.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_2229647
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'White, Jonathan M.'
_publ_section_title
;
 2-(4-Aminophenyl)-1-phenyldiazenium 2,4,6-trinitrophenolate
;
_journal_coeditor_code           FL2338
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o878
_journal_paper_doi               10.1107/S1600536811008968
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 N3 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C12 H12 N3 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C18 H14 N6 O7'
_chemical_formula_weight         426.35
_chemical_melting_point_gt       443
_chemical_melting_point_lt       445
_chemical_name_common            'phenylazoaniline picrate'
_chemical_name_systematic
;
2-(4-Aminophenyl)-1-phenyldiazenium 2,4,6-trinitrophenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.063(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4506(2)
_cell_length_b                   16.8974(5)
_cell_length_c                   19.9386(6)
_cell_measurement_reflns_used    3903
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.738
_cell_measurement_theta_min      3.158
_cell_volume                     1831.75(10)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_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 et al., 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12224
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            red-black
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0369
_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)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                2278
_reflns_number_total             3593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2338.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229647
_cod_database_fobs_code          2229647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x+1/2, -y+1/2, z+1/2'
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 N1 0.5298(2) 0.49802(8) 0.36091(6) 0.0251(4) Uani . . 1.000
N N4 -0.2497(3) 0.32118(10) 0.25985(9) 0.0344(6) Uani . . 1.000
N N11 0.6596(2) 0.54559(8) 0.32635(7) 0.0252(5) Uani . . 1.000
C C1 0.3432(3) 0.45678(9) 0.33086(8) 0.0222(5) Uani . . 1.000
C C2 0.2730(3) 0.45249(10) 0.26070(8) 0.0269(6) Uani . . 1.000
C C3 0.0809(3) 0.40706(10) 0.23773(8) 0.0276(5) Uani . . 1.000
C C4 -0.0594(3) 0.36418(9) 0.28318(8) 0.0238(5) Uani . . 1.000
C C5 0.0074(3) 0.36874(9) 0.35319(8) 0.0254(5) Uani . . 1.000
C C6 0.2047(3) 0.41246(10) 0.37563(8) 0.0264(5) Uani . . 1.000
C C11 0.8581(3) 0.58730(10) 0.35919(8) 0.0242(5) Uani . . 1.000
C C21 1.0003(3) 0.63434(10) 0.32020(9) 0.0296(6) Uani . . 1.000
C C31 1.1992(3) 0.67474(10) 0.35069(9) 0.0343(6) Uani . . 1.000
C C41 1.2563(3) 0.66787(11) 0.41880(9) 0.0385(7) Uani . . 1.000
C C51 1.1132(3) 0.62021(12) 0.45732(9) 0.0410(7) Uani . . 1.000
C C61 0.9138(3) 0.57997(11) 0.42795(9) 0.0336(6) Uani . . 1.000
O O1A 0.5381(2) 0.60880(7) 0.19268(6) 0.0355(4) Uani . . 1.000
O O21A 0.9876(2) 0.55846(7) 0.15684(7) 0.0441(5) Uani . . 1.000
O O22A 0.9183(2) 0.48046(7) 0.07170(7) 0.0434(5) Uani . . 1.000
O O41A 0.5231(2) 0.62072(8) -0.12058(6) 0.0504(5) Uani . . 1.000
O O42A 0.2254(2) 0.70145(8) -0.10480(6) 0.0402(4) Uani . . 1.000
O O61A -0.0343(2) 0.74572(7) 0.11123(7) 0.0408(5) Uani . . 1.000
O O62A 0.2079(2) 0.72543(7) 0.20024(6) 0.0392(5) Uani . . 1.000
N N2A 0.8675(2) 0.53839(9) 0.10537(8) 0.0300(5) Uani . . 1.000
N N4A 0.3933(3) 0.65722(9) -0.08305(7) 0.0330(5) Uani . . 1.000
N N6A 0.1562(3) 0.71719(8) 0.13953(7) 0.0299(5) Uani . . 1.000
C C1A 0.5121(3) 0.62347(9) 0.13155(8) 0.0239(6) Uani . . 1.000
C C2A 0.6597(3) 0.58734(9) 0.08148(8) 0.0238(5) Uani . . 1.000
C C3A 0.6232(3) 0.59705(9) 0.01357(8) 0.0250(6) Uani . . 1.000
C C4A 0.4368(3) 0.64710(10) -0.01148(8) 0.0251(5) Uani . . 1.000
C C5A 0.2883(3) 0.68524(10) 0.03106(8) 0.0245(5) Uani . . 1.000
C C6A 0.3236(3) 0.67494(9) 0.09927(8) 0.0231(5) Uani . . 1.000
H H2 0.36010 0.48120 0.23050 0.0320 Uiso calc R 1.000
H H3 0.03980 0.40380 0.19170 0.0330 Uiso calc R 1.000
H H5 -0.08410 0.34180 0.38350 0.0300 Uiso calc R 1.000
H H6 0.25080 0.41350 0.42140 0.0320 Uiso calc R 1.000
H H11 0.626(3) 0.5560(10) 0.2835(9) 0.041(6) Uiso . . 1.000
H H21 0.96250 0.63870 0.27410 0.0360 Uiso calc R 1.000
H H31 1.29490 0.70670 0.32500 0.0410 Uiso calc R 1.000
H H41 -0.289(3) 0.3182(12) 0.2157(11) 0.061(7) Uiso . . 1.000
H H42 -0.337(4) 0.2946(13) 0.2877(12) 0.077(8) Uiso . . 1.000
H H43 1.39030 0.69510 0.43900 0.0460 Uiso calc R 1.000
H H51 1.15240 0.61550 0.50330 0.0490 Uiso calc R 1.000
H H61 0.81770 0.54830 0.45380 0.0400 Uiso calc R 1.000
H H3A 0.72160 0.57060 -0.01540 0.0300 Uiso calc R 1.000
H H5A 0.16310 0.71820 0.01350 0.0290 Uiso calc R 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
N11 N1 C1 . . . 120.61(13) no
N1 N11 C11 . . . 119.37(13) no
C4 N4 H41 . . . 120.3(12) no
C4 N4 H42 . . . 120.3(15) no
H41 N4 H42 . . . 119.4(19) no
C11 N11 H11 . . . 116.8(11) no
N1 N11 H11 . . . 123.7(11) no
O21A N2A O22A . . . 123.37(13) no
O21A N2A C2A . . . 118.30(14) no
O22A N2A C2A . . . 118.29(14) no
O42A N4A C4A . . . 119.03(14) no
O41A N4A C4A . . . 118.78(14) no
O41A N4A O42A . . . 122.19(14) no
O61A N6A C6A . . . 118.63(14) no
O61A N6A O62A . . . 121.87(15) no
O62A N6A C6A . . . 119.49(14) no
N1 C1 C6 . . . 114.41(14) no
N1 C1 C2 . . . 127.45(15) no
C2 C1 C6 . . . 118.13(14) no
C1 C2 C3 . . . 120.59(15) no
C2 C3 C4 . . . 120.74(15) no
C3 C4 C5 . . . 119.09(14) no
N4 C4 C5 . . . 121.03(15) no
N4 C4 C3 . . . 119.89(15) no
C4 C5 C6 . . . 119.79(15) no
C1 C6 C5 . . . 121.61(15) no
N11 C11 C21 . . . 117.80(14) no
C21 C11 C61 . . . 120.86(16) no
N11 C11 C61 . . . 121.32(15) no
C11 C21 C31 . . . 119.20(16) no
C21 C31 C41 . . . 120.45(16) no
C31 C41 C51 . . . 119.84(16) no
C41 C51 C61 . . . 120.53(17) no
C11 C61 C51 . . . 119.12(16) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C11 C21 H21 . . . 120.00 no
C31 C21 H21 . . . 120.00 no
C41 C31 H31 . . . 120.00 no
C21 C31 H31 . . . 120.00 no
C51 C41 H43 . . . 120.00 no
C31 C41 H43 . . . 120.00 no
C41 C51 H51 . . . 120.00 no
C61 C51 H51 . . . 120.00 no
C51 C61 H61 . . . 120.00 no
C11 C61 H61 . . . 120.00 no
O1A C1A C2A . . . 123.89(14) no
O1A C1A C6A . . . 125.39(15) no
C2A C1A C6A . . . 110.63(14) no
N2A C2A C1A . . . 117.89(14) no
N2A C2A C3A . . . 116.65(14) no
C1A C2A C3A . . . 125.44(15) no
C2A C3A C4A . . . 118.82(15) no
N4A C4A C3A . . . 119.61(15) no
N4A C4A C5A . . . 119.56(15) no
C3A C4A C5A . . . 120.81(15) no
C4A C5A C6A . . . 120.36(15) no
N6A C6A C1A . . . 120.09(14) no
N6A C6A C5A . . . 116.00(14) no
C1A C6A C5A . . . 123.90(15) no
C2A C3A H3A . . . 121.00 no
C4A C3A H3A . . . 121.00 no
C4A C5A H5A . . . 120.00 no
C6A C5A H5A . . . 120.00 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
O1A C1A . . 1.242(2) no
O21A N2A . . 1.225(2) no
O22A N2A . . 1.230(2) no
O41A N4A . . 1.2312(19) no
O42A N4A . . 1.236(2) no
O61A N6A . . 1.2434(19) no
O62A N6A . . 1.2311(18) no
N1 C1 . . 1.339(2) no
N1 N11 . . 1.3002(18) no
N4 C4 . . 1.324(2) no
N11 C11 . . 1.413(2) no
N4 H41 . . 0.89(2) no
N4 H42 . . 0.88(2) no
N11 H11 . . 0.879(18) no
N2A C2A . . 1.455(2) no
N4A C4A . . 1.440(2) no
N6A C6A . . 1.446(2) no
C1 C6 . . 1.422(2) no
C1 C2 . . 1.426(2) no
C2 C3 . . 1.352(2) no
C3 C4 . . 1.425(2) no
C4 C5 . . 1.420(2) no
C5 C6 . . 1.354(2) no
C11 C21 . . 1.387(2) no
C11 C61 . . 1.389(2) no
C21 C31 . . 1.385(2) no
C31 C41 . . 1.377(3) no
C41 C51 . . 1.390(3) no
C51 C61 . . 1.377(2) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C21 H21 . . 0.9300 no
C31 H31 . . 0.9300 no
C41 H43 . . 0.9300 no
C51 H51 . . 0.9300 no
C61 H61 . . 0.9300 no
C1A C2A . . 1.460(2) no
C1A C6A . . 1.460(2) no
C2A C3A . . 1.365(2) no
C3A C4A . . 1.388(2) no
C4A C5A . . 1.374(2) no
C5A C6A . . 1.371(2) no
C3A H3A . . 0.9300 no
C5A H5A . . 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
N11 H11 O1A . 0.879(18) 2.045(18) 2.9039(18) 165.4(16) yes
N4 H41 O41A 3_565 0.89(2) 2.44(2) 3.211(2) 145.0(16) yes
N4 H41 O42A 3_565 0.89(2) 2.29(2) 3.127(2) 156.9(15) yes
N4 H42 O61A 2_445 0.88(2) 2.33(2) 3.170(2) 159(2) yes
N4 H42 O62A 2_445 0.88(2) 2.36(2) 3.126(2) 145(2) yes
C2 H2 O1A . 0.93 2.50 3.344(2) 151 no
C3A H3A O22A 3_765 0.93 2.48 3.384(2) 163 no
C5A H5A O61A . 0.93 2.34 2.663(2) 100 no
C21 H21 O62A 1_655 0.93 2.53 3.123(2) 122 no
C31 H31 O62A 1_655 0.93 2.52 3.123(2) 123 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
C1 N1 N11 C11 . . . . -178.90(14) no
N11 N1 C1 C2 . . . . 5.7(2) no
N11 N1 C1 C6 . . . . -174.89(14) no
N1 N11 C11 C21 . . . . 176.74(14) no
N1 N11 C11 C61 . . . . -1.6(2) no
O21A N2A C2A C1A . . . . -36.9(2) no
O21A N2A C2A C3A . . . . 141.62(15) no
O22A N2A C2A C1A . . . . 145.46(15) no
O22A N2A C2A C3A . . . . -36.1(2) no
O41A N4A C4A C5A . . . . -177.77(16) no
O42A N4A C4A C3A . . . . 179.40(15) no
O41A N4A C4A C3A . . . . 0.2(2) no
O42A N4A C4A C5A . . . . 1.4(2) no
O61A N6A C6A C1A . . . . -163.87(14) no
O61A N6A C6A C5A . . . . 14.6(2) no
O62A N6A C6A C5A . . . . -163.83(15) no
O62A N6A C6A C1A . . . . 17.7(2) no
C6 C1 C2 C3 . . . . -0.4(2) no
N1 C1 C6 C5 . . . . 178.82(15) no
N1 C1 C2 C3 . . . . 179.05(16) no
C2 C1 C6 C5 . . . . -1.7(2) no
C1 C2 C3 C4 . . . . 1.7(3) no
C2 C3 C4 N4 . . . . 178.74(16) no
C2 C3 C4 C5 . . . . -1.0(2) no
C3 C4 C5 C6 . . . . -1.1(2) no
N4 C4 C5 C6 . . . . 179.24(16) no
C4 C5 C6 C1 . . . . 2.4(2) no
N11 C11 C21 C31 . . . . -178.72(15) no
C61 C11 C21 C31 . . . . -0.4(3) no
N11 C11 C61 C51 . . . . 178.27(16) no
C21 C11 C61 C51 . . . . 0.0(3) no
C11 C21 C31 C41 . . . . 0.5(3) no
C21 C31 C41 C51 . . . . -0.1(3) no
C31 C41 C51 C61 . . . . -0.3(3) no
C41 C51 C61 C11 . . . . 0.3(3) no
O1A C1A C2A N2A . . . . -7.4(2) no
O1A C1A C2A C3A . . . . 174.32(16) no
C6A C1A C2A N2A . . . . 175.85(13) no
C6A C1A C2A C3A . . . . -2.5(2) no
O1A C1A C6A N6A . . . . 3.5(2) no
O1A C1A C6A C5A . . . . -174.90(16) no
C2A C1A C6A N6A . . . . -179.79(14) no
C2A C1A C6A C5A . . . . 1.8(2) no
N2A C2A C3A C4A . . . . -176.08(14) no
C1A C2A C3A C4A . . . . 2.3(2) no
C2A C3A C4A N4A . . . . -179.13(15) no
C2A C3A C4A C5A . . . . -1.2(2) no
N4A C4A C5A C6A . . . . 178.58(15) no
C3A C4A C5A C6A . . . . 0.6(3) no
C4A C5A C6A N6A . . . . -179.50(15) no
C4A C5A C6A C1A . . . . -1.1(3) no
