#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/97/2229754.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_2229754
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline
;
_journal_coeditor_code           LH5220
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o948
_journal_paper_doi               10.1107/S160053681101004X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H12 N6 O6'
_chemical_formula_moiety         'C18 H12 N6 O6'
_chemical_formula_sum            'C18 H12 N6 O6'
_chemical_formula_weight         408.34
_chemical_name_common            N-picryl(phenylazo)aniline
_chemical_name_systematic
;
2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 98.160(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4255(4)
_cell_length_b                   7.6613(4)
_cell_length_c                   16.1510(9)
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      3.482
_cell_volume                     909.51(9)
_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      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0763
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6768
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         3.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_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         -0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0371
_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)+(0.0210P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                1407
_reflns_number_total             2297
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5220.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2229754
_cod_database_fobs_code          2229754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O O21A 0.7894(3) 0.0405(2) 0.33042(15) 0.0557(8) Uani . . 1.000
O O22A 0.8395(3) -0.0131(3) 0.20499(15) 0.0673(10) Uani . . 1.000
O O41A 0.7046(3) 0.3737(3) -0.01934(12) 0.0524(8) Uani . . 1.000
O O42A 0.5573(3) 0.6113(3) -0.00428(13) 0.0733(10) Uani . . 1.000
O O61A 0.4815(3) 0.8150(3) 0.26498(14) 0.0582(9) Uani . . 1.000
O O62A 0.4238(2) 0.6124(3) 0.35215(12) 0.0467(7) Uani . . 1.000
N N1 0.6941(3) 0.3543(3) 0.36913(14) 0.0379(8) Uani . . 1.000
N N2A 0.7860(3) 0.0827(3) 0.25675(17) 0.0438(10) Uani . . 1.000
N N4 0.8515(3) 0.7986(3) 0.64591(15) 0.0376(8) Uani . . 1.000
N N4A 0.6334(3) 0.4775(3) 0.02299(15) 0.0403(9) Uani . . 1.000
N N6A 0.4931(3) 0.6655(3) 0.29240(16) 0.0397(9) Uani . . 1.000
N N41 0.7964(3) 0.7460(3) 0.71112(15) 0.0388(8) Uani . . 1.000
C C1 0.7256(3) 0.4761(4) 0.43607(17) 0.0343(10) Uani . . 1.000
C C1A 0.6660(3) 0.3836(3) 0.28559(17) 0.0304(9) Uani . . 1.000
C C2 0.8086(3) 0.6339(3) 0.42983(17) 0.0367(10) Uani . . 1.000
C C2A 0.7143(3) 0.2547(3) 0.22900(18) 0.0323(9) Uani . . 1.000
C C3 0.8466(3) 0.7381(4) 0.50001(17) 0.0363(10) Uani . . 1.000
C C3A 0.7034(3) 0.2855(3) 0.14441(17) 0.0325(10) Uani . . 1.000
C C4 0.8030(3) 0.6843(4) 0.57641(18) 0.0357(10) Uani . . 1.000
C C4A 0.6397(3) 0.4442(4) 0.11242(17) 0.0304(9) Uani . . 1.000
C C5 0.7209(4) 0.5221(4) 0.58222(18) 0.0420(11) Uani . . 1.000
C C5A 0.5793(3) 0.5688(3) 0.16261(17) 0.0321(10) Uani . . 1.000
C C6 0.6810(4) 0.4184(4) 0.51302(18) 0.0429(11) Uani . . 1.000
C C6A 0.5887(3) 0.5373(3) 0.24652(17) 0.0301(9) Uani . . 1.000
C C11 0.9043(4) 1.0521(4) 0.92620(19) 0.0475(11) Uani . . 1.000
C C21 0.9363(3) 1.1240(4) 0.8506(2) 0.0455(11) Uani . . 1.000
C C31 0.9046(3) 1.0274(4) 0.77855(17) 0.0361(10) Uani . . 1.000
C C41 0.8401(3) 0.8580(3) 0.78142(17) 0.0313(10) Uani . . 1.000
C C51 0.8078(3) 0.7876(4) 0.85652(18) 0.0391(10) Uani . . 1.000
C C61 0.8423(4) 0.8851(4) 0.92962(19) 0.0437(11) Uani . . 1.000
H H1 0.69280 0.24650 0.38380 0.0450 Uiso calc R 1.000
H H2 0.83930 0.67080 0.37880 0.0440 Uiso calc R 1.000
H H3 0.90220 0.84590 0.49580 0.0430 Uiso calc R 1.000
H H3A 0.73870 0.19990 0.10920 0.0390 Uiso calc R 1.000
H H5 0.69290 0.48390 0.63360 0.0500 Uiso calc R 1.000
H H5A 0.53250 0.67380 0.14000 0.0390 Uiso calc R 1.000
H H6 0.62490 0.31080 0.51700 0.0510 Uiso calc R 1.000
H H11 0.92550 1.11840 0.97480 0.0570 Uiso calc R 1.000
H H21 0.97920 1.23780 0.84890 0.0540 Uiso calc R 1.000
H H31 0.92630 1.07520 0.72800 0.0430 Uiso calc R 1.000
H H51 0.76280 0.67450 0.85820 0.0470 Uiso calc R 1.000
H H61 0.82320 0.83690 0.98050 0.0520 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 N1 C1A . . . 129.4(2) n
O21A N2A O22A . . . 122.7(2) n
O21A N2A C2A . . . 119.2(2) n
O22A N2A C2A . . . 118.0(3) n
N41 N4 C4 . . . 112.9(2) n
O41A N4A O42A . . . 124.1(2) n
O41A N4A C4A . . . 119.1(2) n
O42A N4A C4A . . . 116.8(2) n
O61A N6A O62A . . . 125.3(2) n
O61A N6A C6A . . . 117.1(2) n
O62A N6A C6A . . . 117.5(2) n
N4 N41 C41 . . . 114.4(2) n
C1 N1 H1 . . . 115.00 no
C1A N1 H1 . . . 115.00 no
N1 C1 C2 . . . 123.5(2) n
C2 C1 C6 . . . 120.6(3) no
N1 C1 C6 . . . 115.7(3) n
C2A C1A C6A . . . 114.4(2) no
N1 C1A C6A . . . 125.2(2) n
N1 C1A C2A . . . 120.4(2) n
C1 C2 C3 . . . 119.5(2) no
C1A C2A C3A . . . 122.2(2) no
N2A C2A C1A . . . 122.7(2) n
N2A C2A C3A . . . 115.1(2) n
C2 C3 C4 . . . 120.9(3) no
C2A C3A C4A . . . 119.5(2) no
N4 C4 C5 . . . 123.9(3) n
N4 C4 C3 . . . 117.0(3) n
C3 C4 C5 . . . 119.1(3) no
N4A C4A C5A . . . 119.8(2) n
N4A C4A C3A . . . 119.1(2) n
C3A C4A C5A . . . 121.1(3) no
C4 C5 C6 . . . 120.6(3) no
C4A C5A C6A . . . 119.3(2) no
C1 C6 C5 . . . 119.3(3) no
N6A C6A C1A . . . 121.6(2) n
N6A C6A C5A . . . 114.9(2) n
C1A C6A C5A . . . 123.2(2) no
C21 C11 C61 . . . 120.5(3) no
C11 C21 C31 . . . 120.1(3) no
C21 C31 C41 . . . 119.7(3) no
N41 C41 C51 . . . 114.7(2) n
N41 C41 C31 . . . 125.3(2) n
C31 C41 C51 . . . 120.0(3) no
C41 C51 C61 . . . 120.2(3) no
C11 C61 C51 . . . 119.5(3) 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
C2A C3A H3A . . . 120.00 no
C4A C3A H3A . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C4A C5A H5A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C21 C11 H11 . . . 120.00 no
C61 C11 H11 . . . 120.00 no
C11 C21 H21 . . . 120.00 no
C31 C21 H21 . . . 120.00 no
C21 C31 H31 . . . 120.00 no
C41 C31 H31 . . . 120.00 no
C41 C51 H51 . . . 120.00 no
C61 C51 H51 . . . 120.00 no
C11 C61 H61 . . . 120.00 no
C51 C61 H61 . . . 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
O21A N2A . . 1.230(4) n
O22A N2A . . 1.221(3) n
O41A N4A . . 1.217(3) n
O42A N4A . . 1.222(3) n
O61A N6A . . 1.227(3) n
O62A N6A . . 1.226(3) n
N1 C1 . . 1.422(4) n
N1 C1A . . 1.354(4) n
N2A C2A . . 1.467(3) n
N4 N41 . . 1.250(3) n
N4 C4 . . 1.429(4) n
N4A C4A . . 1.461(4) n
N6A C6A . . 1.472(3) n
N41 C41 . . 1.423(3) n
N1 H1 . . 0.8600 no
C1 C6 . . 1.402(4) no
C1 C2 . . 1.367(4) no
C1A C2A . . 1.426(4) no
C1A C6A . . 1.418(3) no
C2 C3 . . 1.382(4) no
C2A C3A . . 1.378(4) no
C3 C4 . . 1.382(4) no
C3A C4A . . 1.378(4) no
C4 C5 . . 1.393(4) no
C4A C5A . . 1.369(4) no
C5 C6 . . 1.369(4) no
C5A C6A . . 1.369(4) no
C11 C61 . . 1.364(4) no
C11 C21 . . 1.390(4) no
C21 C31 . . 1.371(4) no
C31 C41 . . 1.386(4) no
C41 C51 . . 1.379(4) no
C51 C61 . . 1.390(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C3A H3A . . 0.9300 no
C5 H5 . . 0.9300 no
C5A H5A . . 0.9300 no
C6 H6 . . 0.9300 no
C11 H11 . . 0.9300 no
C21 H21 . . 0.9300 no
C31 H31 . . 0.9300 no
C51 H51 . . 0.9300 no
C61 H61 . . 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
N1 H1 O21A . 0.86 1.98 2.607(3) 129 yes
C3A H3A O22A . 0.93 2.30 2.633(3) 100 no
C5 H5 O61A 2_646 0.93 2.58 3.453(4) 157 no
C11 H11 O41A 1_566 0.93 2.56 3.068(4) 115 no
C21 H21 O22A 2_766 0.93 2.56 3.425(4) 155 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
C1A N1 C1 C2 . . . . -29.4(4) no
C1A N1 C1 C6 . . . . 156.3(3) no
C1 N1 C1A C2A . . . . 152.5(2) no
C1 N1 C1A C6A . . . . -27.7(4) no
O21A N2A C2A C1A . . . . 7.0(4) no
O21A N2A C2A C3A . . . . -175.4(2) no
O22A N2A C2A C1A . . . . -173.3(2) no
O22A N2A C2A C3A . . . . 4.3(3) no
C4 N4 N41 C41 . . . . -179.2(2) no
N41 N4 C4 C3 . . . . 175.4(2) no
N41 N4 C4 C5 . . . . -6.7(4) no
O41A N4A C4A C3A . . . . -8.9(4) no
O41A N4A C4A C5A . . . . 172.4(2) no
O42A N4A C4A C3A . . . . 172.0(2) no
O42A N4A C4A C5A . . . . -6.7(3) no
O61A N6A C6A C1A . . . . 157.5(2) no
O61A N6A C6A C5A . . . . -29.3(3) no
O62A N6A C6A C1A . . . . -26.1(3) no
O62A N6A C6A C5A . . . . 147.1(2) no
N4 N41 C41 C31 . . . . 12.6(4) no
N4 N41 C41 C51 . . . . -169.5(2) no
N1 C1 C2 C3 . . . . -174.9(2) no
C6 C1 C2 C3 . . . . -0.8(4) no
N1 C1 C6 C5 . . . . 174.7(3) no
C2 C1 C6 C5 . . . . 0.2(4) no
N1 C1A C2A N2A . . . . 3.5(3) no
N1 C1A C2A C3A . . . . -174.0(2) no
C6A C1A C2A N2A . . . . -176.3(2) no
C6A C1A C2A C3A . . . . 6.3(3) no
N1 C1A C6A N6A . . . . -14.0(4) no
N1 C1A C6A C5A . . . . 173.3(2) no
C2A C1A C6A N6A . . . . 165.7(2) no
C2A C1A C6A C5A . . . . -7.0(3) no
C1 C2 C3 C4 . . . . 0.5(4) no
N2A C2A C3A C4A . . . . -179.3(2) no
C1A C2A C3A C4A . . . . -1.6(4) no
C2 C3 C4 N4 . . . . 178.5(2) no
C2 C3 C4 C5 . . . . 0.5(4) no
C2A C3A C4A N4A . . . . 178.3(2) no
C2A C3A C4A C5A . . . . -3.0(4) no
N4 C4 C5 C6 . . . . -178.9(3) no
C3 C4 C5 C6 . . . . -1.1(4) no
N4A C4A C5A C6A . . . . -178.9(2) no
C3A C4A C5A C6A . . . . 2.4(4) no
C4 C5 C6 C1 . . . . 0.8(4) no
C4A C5A C6A N6A . . . . -170.2(2) no
C4A C5A C6A C1A . . . . 2.9(4) no
C61 C11 C21 C31 . . . . 0.4(4) no
C21 C11 C61 C51 . . . . -1.2(4) no
C11 C21 C31 C41 . . . . 0.2(4) no
C21 C31 C41 N41 . . . . 178.0(2) no
C21 C31 C41 C51 . . . . 0.1(4) no
N41 C41 C51 C61 . . . . -179.0(2) no
C31 C41 C51 C61 . . . . -1.0(4) no
C41 C51 C61 C11 . . . . 1.5(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 483394
