#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229902.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_2229902
loop_
_publ_author_name
'Wang, Wan-Qiang'
_publ_section_title
;
 Picric acid--2,4,6-trichloroaniline (1/1)
;
_journal_coeditor_code           ZS2097
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o860
_journal_paper_doi               10.1107/S160053681100571X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H4 Cl3 N, C6 H3 N3 O7'
_chemical_formula_moiety         'C6 H4 Cl3 N, C6 H3 N3 O7'
_chemical_formula_sum            'C12 H7 Cl3 N4 O7'
_chemical_formula_weight         425.57
_chemical_name_systematic
;
Picric acid--2,4,6-trichloroaniline (1/1)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2162(14)
_cell_length_b                   10.0174(14)
_cell_length_c                   35.051(5)
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.18
_cell_measurement_theta_min      2.50
_cell_volume                     3236.0(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(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       'φ and ω scans'
_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  0.0756
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            19589
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0581
_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/[σ²(Fo²)+(0.0381P)²+1.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2287
_reflns_number_total             3186
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2097.cif
_cod_data_source_block           I
_cod_database_code               2229902
_cod_database_fobs_code          2229902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4507(4) 0.4557(3) 0.57639(9) 0.0373(8) Uani d . 1 . .
C C2 0.5792(3) 0.4955(3) 0.55888(10) 0.0396(8) Uani d . 1 . .
C C3 0.5881(4) 0.6056(4) 0.53560(10) 0.0422(9) Uani d . 1 . .
H H3 0.6760 0.6295 0.5245 0.051 Uiso calc R 1 . .
C C4 0.4651(4) 0.6801(3) 0.52893(9) 0.0390(8) Uani d . 1 . .
C C5 0.3352(4) 0.6456(3) 0.54541(10) 0.0415(9) Uani d . 1 . .
H H5 0.2523 0.6960 0.5408 0.050 Uiso calc R 1 . .
C C6 0.3293(3) 0.5361(3) 0.56874(9) 0.0375(8) Uani d . 1 . .
C C7 0.4085(3) 0.4501(3) 0.70238(9) 0.0325(7) Uani d . 1 . .
C C8 0.5325(3) 0.3724(3) 0.70914(9) 0.0343(8) Uani d . 1 . .
C C9 0.6640(3) 0.3992(3) 0.69253(9) 0.0360(8) Uani d . 1 . .
H H9 0.7437 0.3447 0.6972 0.043 Uiso calc R 1 . .
C C10 0.6760(4) 0.5082(3) 0.66889(9) 0.0379(8) Uani d . 1 . .
C C11 0.5597(4) 0.5899(3) 0.66136(9) 0.0379(8) Uani d . 1 . .
H H11 0.5694 0.6642 0.6456 0.046 Uiso calc R 1 . .
C C12 0.4278(3) 0.5584(3) 0.67784(9) 0.0324(8) Uani d . 1 . .
Cl Cl1 0.73498(10) 0.40282(11) 0.56753(3) 0.0607(3) Uani d . 1 . .
Cl Cl2 0.47396(11) 0.81912(11) 0.49911(3) 0.0592(3) Uani d . 1 . .
Cl Cl3 0.16542(10) 0.49502(10) 0.59030(3) 0.0560(3) Uani d . 1 . .
N N1 0.5268(3) 0.2597(3) 0.73550(9) 0.0478(8) Uani d . 1 . .
N N2 0.8171(3) 0.5390(4) 0.65186(9) 0.0507(8) Uani d . 1 . .
N N3 0.3064(3) 0.6474(3) 0.66942(9) 0.0452(8) Uani d . 1 . .
N N4 0.4439(4) 0.3486(3) 0.60078(10) 0.0520(8) Uani d D 1 . .
H H4A 0.512(3) 0.290(3) 0.6009(11) 0.062 Uiso d D 1 . .
H H4B 0.359(2) 0.332(4) 0.6079(11) 0.062 Uiso d D 1 . .
O O1 0.2826(3) 0.4170(2) 0.71812(7) 0.0494(7) Uani d . 1 . .
H H1A 0.218(5) 0.479(4) 0.7114(11) 0.074 Uiso d . 1 . .
O O2 0.4487(4) 0.2669(3) 0.76291(9) 0.0979(13) Uani d . 1 . .
O O3 0.6055(3) 0.1642(3) 0.72928(8) 0.0643(8) Uani d . 1 . .
O O4 0.9144(3) 0.4573(3) 0.65587(9) 0.0711(9) Uani d . 1 . .
O O5 0.8294(3) 0.6445(3) 0.63491(9) 0.0726(9) Uani d . 1 . .
O O6 0.3275(3) 0.7422(3) 0.64860(8) 0.0672(8) Uani d . 1 . .
O O7 0.1878(3) 0.6247(3) 0.68450(8) 0.0602(8) Uani d . 1 . .
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'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
_geom_angle_publ_flag
N4 C1 C2 . . 122.5(3) ?
N4 C1 C6 . . 122.0(3) ?
C2 C1 C6 . . 115.4(3) ?
C3 C2 C1 . . 122.8(3) ?
C3 C2 Cl1 . . 118.9(3) ?
C1 C2 Cl1 . . 118.3(3) ?
C2 C3 C4 . . 119.1(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 120.7(3) ?
C5 C4 Cl2 . . 119.6(3) ?
C3 C4 Cl2 . . 119.8(3) ?
C6 C5 C4 . . 119.1(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C1 . . 122.8(3) ?
C5 C6 Cl3 . . 118.9(3) ?
C1 C6 Cl3 . . 118.3(3) ?
O1 C7 C12 . . 124.2(3) ?
O1 C7 C8 . . 120.2(3) ?
C12 C7 C8 . . 115.5(3) ?
C9 C8 C7 . . 122.6(3) ?
C9 C8 N1 . . 116.9(3) ?
C7 C8 N1 . . 120.4(3) ?
C8 C9 C10 . . 118.9(3) ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
C9 C10 C11 . . 121.7(3) ?
C9 C10 N2 . . 119.0(3) ?
C11 C10 N2 . . 119.3(3) ?
C10 C11 C12 . . 118.0(3) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
C11 C12 C7 . . 123.2(3) ?
C11 C12 N3 . . 116.7(3) ?
C7 C12 N3 . . 120.0(3) ?
O2 N1 O3 . . 123.0(3) ?
O2 N1 C8 . . 118.8(3) ?
O3 N1 C8 . . 118.1(3) ?
O5 N2 O4 . . 124.7(3) ?
O5 N2 C10 . . 117.7(3) ?
O4 N2 C10 . . 117.6(3) ?
O6 N3 O7 . . 122.9(3) ?
O6 N3 C12 . . 118.4(3) ?
O7 N3 C12 . . 118.6(3) ?
C1 N4 H4A . . 120(3) ?
C1 N4 H4B . . 112(3) ?
H4A N4 H4B . . 123(4) ?
C7 O1 H1A . . 108(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N4 . 1.373(4) ?
C1 C2 . 1.392(5) ?
C1 C6 . 1.404(5) ?
C2 C3 . 1.374(5) ?
C2 Cl1 . 1.736(3) ?
C3 C4 . 1.377(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 Cl2 . 1.743(3) ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 Cl3 . 1.739(3) ?
C7 O1 . 1.327(4) ?
C7 C12 . 1.396(4) ?
C7 C8 . 1.404(4) ?
C8 C9 . 1.371(4) ?
C8 N1 . 1.460(4) ?
C9 C10 . 1.374(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.375(5) ?
C10 N2 . 1.464(4) ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.9300 ?
C12 N3 . 1.461(4) ?
N1 O2 . 1.202(4) ?
N1 O3 . 1.221(4) ?
N2 O5 . 1.218(4) ?
N2 O4 . 1.222(4) ?
N3 O6 . 1.213(4) ?
N3 O7 . 1.235(4) ?
N4 H4A . 0.854(18) ?
N4 H4B . 0.842(18) ?
O1 H1A . 0.89(4) ?
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
O1 H1A O7 . 0.89(4) 1.76(4) 2.546(4) 145(4)
N4 H4A Cl1 . 0.854(18) 2.62(4) 2.975(3) 106(3)
N4 H4A O5 8_755 0.854(18) 2.39(2) 3.159(4) 150(3)
N4 H4B Cl3 . 0.842(18) 2.49(3) 2.979(3) 118(3)
N4 H4B O6 8_655 0.842(18) 2.40(2) 3.194(4) 156(4)
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
N4 C1 C2 C3 . . . . -177.4(3) ?
C6 C1 C2 C3 . . . . -0.1(5) ?
N4 C1 C2 Cl1 . . . . 1.6(5) ?
C6 C1 C2 Cl1 . . . . 179.0(2) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
Cl1 C2 C3 C4 . . . . -179.4(3) ?
C2 C3 C4 C5 . . . . 0.4(5) ?
C2 C3 C4 Cl2 . . . . -179.4(3) ?
C3 C4 C5 C6 . . . . 0.2(5) ?
Cl2 C4 C5 C6 . . . . 179.9(3) ?
C4 C5 C6 C1 . . . . -0.7(5) ?
C4 C5 C6 Cl3 . . . . 178.7(3) ?
N4 C1 C6 C5 . . . . 178.0(3) ?
C2 C1 C6 C5 . . . . 0.6(5) ?
N4 C1 C6 Cl3 . . . . -1.4(5) ?
C2 C1 C6 Cl3 . . . . -178.8(2) ?
O1 C7 C8 C9 . . . . 177.6(3) ?
C12 C7 C8 C9 . . . . -0.7(5) ?
O1 C7 C8 N1 . . . . -4.1(5) ?
C12 C7 C8 N1 . . . . 177.6(3) ?
C7 C8 C9 C10 . . . . 1.4(5) ?
N1 C8 C9 C10 . . . . -177.0(3) ?
C8 C9 C10 C11 . . . . -0.4(5) ?
C8 C9 C10 N2 . . . . 178.5(3) ?
C9 C10 C11 C12 . . . . -1.0(5) ?
N2 C10 C11 C12 . . . . -180.0(3) ?
C10 C11 C12 C7 . . . . 1.7(5) ?
C10 C11 C12 N3 . . . . 179.8(3) ?
O1 C7 C12 C11 . . . . -179.0(3) ?
C8 C7 C12 C11 . . . . -0.8(5) ?
O1 C7 C12 N3 . . . . 2.9(5) ?
C8 C7 C12 N3 . . . . -178.8(3) ?
C9 C8 N1 O2 . . . . 144.8(4) ?
C7 C8 N1 O2 . . . . -33.6(5) ?
C9 C8 N1 O3 . . . . -32.8(5) ?
C7 C8 N1 O3 . . . . 148.8(3) ?
C9 C10 N2 O5 . . . . -171.2(3) ?
C11 C10 N2 O5 . . . . 7.8(5) ?
C9 C10 N2 O4 . . . . 8.4(5) ?
C11 C10 N2 O4 . . . . -172.6(3) ?
C11 C12 N3 O6 . . . . 0.4(4) ?
C7 C12 N3 O6 . . . . 178.5(3) ?
C11 C12 N3 O7 . . . . -178.0(3) ?
C7 C12 N3 O7 . . . . 0.2(5) ?
