#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223271.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_2223271
loop_
_publ_author_name
'Li, Yan-jun'
_publ_section_title
;
 4-Nitroaniline--picric acid (2/1)
;
_journal_coeditor_code           BG2290
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2566
_journal_paper_doi               10.1107/S1600536809037416
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H3 N3 O7, 0.5C6 H6 N2 O2'
_chemical_formula_moiety         'C6 H3 N3 O7, 0.5(C6 H6 N2 O2)'
_chemical_formula_sum            'C9 H6 N4 O8'
_chemical_formula_weight         298.18
_chemical_name_systematic
;
4-Nitroaniline--picric acid (2/1)
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   23.534(2)
_cell_length_b                   9.3318(8)
_cell_length_c                   10.5047(9)
_cell_measurement_reflns_used    5243
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.35
_cell_volume                     2307.0(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16332
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.262
_refine_ls_extinction_coef       0.0032(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0464
_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)+(0.0712P)²+0.2759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2154
_reflns_number_total             2855
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2290.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223271
_cod_database_fobs_code          2223271
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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 0.66852(7) 0.40572(18) 0.75606(17) 0.0504(4) Uani d . 1 . .
H H1 0.6733 0.5023 0.7753 0.061 Uiso calc PR 0.194(3) A 2
C C2 0.69244(6) 0.29633(18) 0.83061(16) 0.0496(4) Uani d D 1 A .
C C3 0.68653(7) 0.15487(18) 0.80130(17) 0.0517(4) Uani d . 1 . .
H H3 0.7032 0.0852 0.8524 0.062 Uiso calc R 1 A .
C C4 0.65585(7) 0.11617(18) 0.69592(17) 0.0511(4) Uani d D 1 A .
C C5 0.63050(7) 0.21640(19) 0.61822(16) 0.0508(4) Uani d . 1 . .
H H5 0.6098 0.1890 0.5468 0.061 Uiso calc PR 0.806(3) A 1
C C6 0.63686(6) 0.35912(17) 0.65015(16) 0.0488(4) Uani d D 1 A .
C C7 0.5000 0.6849(3) 0.2500 0.0505(5) Uani d S 1 . .
C C8 0.52386(7) 0.76184(19) 0.35141(16) 0.0533(4) Uani d . 1 . .
H H8 0.5397 0.7127 0.4198 0.064 Uiso calc R 1 . .
C C9 0.52404(7) 0.90824(19) 0.35084(15) 0.0533(4) Uani d . 1 . .
H H9 0.5403 0.9585 0.4181 0.064 Uiso calc R 1 . .
C C10 0.5000 0.9812(3) 0.2500 0.0515(6) Uani d S 1 . .
N N4 0.5000 0.5397(3) 0.2500 0.0760(7) Uani d S 1 . .
H H4A 0.5148 0.4936 0.3127 0.091 Uiso d R 1 . .
N N5 0.5000 1.1374(3) 0.2500 0.0705(6) Uani d S 1 . .
N N1 0.72518(7) 0.33052(17) 0.94650(15) 0.0607(4) Uani d D 1 . .
N N2 0.64972(8) -0.03633(18) 0.66686(19) 0.0733(5) Uani d D 1 . .
N N3 0.60883(7) 0.46447(16) 0.56958(16) 0.0598(4) Uani d . 1 . .
O O1 0.67753(7) 0.54438(16) 0.78695(17) 0.0670(6) Uani d PD 0.81(2) A 1
H H1A 0.6603 0.5962 0.7370 0.080 Uiso calc PR 0.806(3) A 1
O O2 0.7225(5) 0.4511(5) 0.9832(7) 0.084(2) Uani d PD 0.55(3) A 1
O O3 0.7584(9) 0.2434(12) 0.980(2) 0.130(5) Uani d PD 0.55(3) A 1
O O5 0.6212(4) -0.0676(7) 0.5744(6) 0.100(2) Uani d PD 0.77(4) A 1
O O4 0.6739(6) -0.1218(7) 0.7350(9) 0.108(2) Uani d PD 0.77(4) A 1
O O1' 0.6057(3) 0.1603(7) 0.5099(6) 0.079(3) Uani d PD 0.19(2) A 2
H H1' 0.6101 0.0731 0.5088 0.119 Uiso calc PR 0.194(3) A 2
O O2' 0.7386(8) 0.4462(8) 0.9798(8) 0.093(3) Uani d PD 0.45(3) A 2
O O3' 0.7319(7) 0.2298(7) 1.0257(8) 0.082(3) Uani d PD 0.45(3) A 2
O O4' 0.6609(16) -0.120(3) 0.752(2) 0.106(8) Uani d PD 0.23(4) A 2
O O5' 0.6331(17) -0.077(3) 0.5624(14) 0.108(8) Uani d PD 0.23(4) A 2
O O6 0.58058(7) 0.42228(16) 0.48088(16) 0.0820(5) Uani d . 1 A .
O O7 0.61414(7) 0.59241(15) 0.59443(18) 0.0839(5) Uani d . 1 A .
O O8 0.52462(9) 1.20034(17) 0.33516(17) 0.1041(7) 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'
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
O1 C1 C2 . . 119.97(16) no
O1 C1 C6 . . 124.67(16) no
C2 C1 C6 . . 115.35(15) no
C2 C1 H1 . . 122.3 no
C6 C1 H1 . . 122.3 no
C3 C2 C1 . . 122.50(16) no
C3 C2 N1 . . 116.69(15) no
C1 C2 N1 . . 120.81(15) no
C2 C3 C4 . . 119.45(16) no
C2 C3 H3 . . 120.3 no
C4 C3 H3 . . 120.3 no
C3 C4 C5 . . 121.88(16) no
C3 C4 N2 . . 118.49(16) no
C5 C4 N2 . . 119.63(16) no
C4 C5 C6 . . 117.63(16) no
C4 C5 O1' . . 114.4(3) no
C6 C5 O1' . . 127.7(3) no
C4 C5 H5 . . 121.2 no
C6 C5 H5 . . 121.2 no
C5 C6 C1 . . 123.16(15) no
C5 C6 N3 . . 117.44(15) no
C1 C6 N3 . . 119.39(15) no
N4 C7 C8 . . 120.81(11) no
N4 C7 C8 . 3_655 120.81(11) no
C8 C7 C8 . 3_655 118.4(2) no
C9 C8 C7 . . 120.67(16) no
C9 C8 H8 . . 119.7 no
C7 C8 H8 . . 119.7 no
C8 C9 C10 . . 119.70(16) no
C8 C9 H9 . . 120.2 no
C10 C9 H9 . . 120.2 no
C9 C10 C9 . 3_655 120.9(2) no
C9 C10 N5 . . 119.56(11) no
C9 C10 N5 3_655 . 119.56(11) no
C7 N4 H4A . . 120.0 no
O8 N5 O8 3_655 . 122.3(3) no
O8 N5 C10 3_655 . 118.85(13) no
O8 N5 C10 . . 118.85(13) no
O2' N1 O3 . . 111.4(6) no
O3 N1 O2 . . 126.1(5) no
O2' N1 O3' . . 116.8(5) no
O2 N1 O3' . . 119.7(6) no
O2' N1 C2 . . 125.7(5) no
O3 N1 C2 . . 116.3(4) no
O2 N1 C2 . . 116.3(4) no
O3' N1 C2 . . 116.6(4) no
O4 N2 O5 . . 124.9(4) no
O5 N2 O4' . . 123.6(15) no
O4 N2 O5' . . 118.4(16) no
O4' N2 O5' . . 122.1(15) no
O4 N2 C4 . . 118.0(4) no
O5 N2 C4 . . 117.0(3) no
O4' N2 C4 . . 116.7(13) no
O5' N2 C4 . . 121.3(13) no
O6 N3 O7 . . 122.38(16) no
O6 N3 C6 . . 118.48(15) no
O7 N3 C6 . . 119.13(16) no
C1 O1 H1A . . 109.5 no
C5 O1' H1' . . 109.5 no
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 O1 . 1.351(2) no
C1 C2 . 1.404(2) no
C1 C6 . 1.408(2) no
C1 H1 . 0.9300 no
C2 C3 . 1.363(2) no
C2 N1 . 1.476(2) no
C3 C4 . 1.370(2) no
C3 H3 . 0.9300 no
C4 C5 . 1.377(2) no
C4 N2 . 1.463(2) no
C5 C6 . 1.382(2) no
C5 O1' . 1.382(6) no
C5 H5 . 0.9300 no
C6 N3 . 1.455(2) no
C7 N4 . 1.355(3) no
C7 C8 . 1.402(2) no
C7 C8 3_655 1.402(2) no
C8 C9 . 1.366(2) no
C8 H8 . 0.9300 no
C9 C10 . 1.381(2) no
C9 H9 . 0.9300 no
C10 C9 3_655 1.381(2) no
C10 N5 . 1.457(3) no
N4 H4A . 0.8600 no
N5 O8 3_655 1.2169(18) no
N5 O8 . 1.2169(18) no
N1 O2' . 1.178(6) no
N1 O3 . 1.182(5) no
N1 O2 . 1.191(5) no
N1 O3' . 1.265(5) no
N2 O4 . 1.214(5) no
N2 O5 . 1.216(4) no
N2 O4' . 1.221(10) no
N2 O5' . 1.225(10) no
N3 O6 . 1.210(2) no
N3 O7 . 1.228(2) no
O1 H1A . 0.8200 no
O1' H1' . 0.8200 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
C3 H3 O2 8_755 0.93 2.55 3.442(10) 160.5 yes
C9 H9 O5 1_565 0.93 2.53 3.286(4) 139.0 yes
N4 H4A O6 . 0.86 2.44 3.2677(16) 161.2 yes
O1 H1A O7 . 0.82 1.85 2.553(2) 142.8 yes
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
O1 C1 C2 C3 . . . . -177.52(17) no
C6 C1 C2 C3 . . . . 1.3(2) no
O1 C1 C2 N1 . . . . 3.0(2) no
C6 C1 C2 N1 . . . . -178.16(14) no
C1 C2 C3 C4 . . . . -0.5(3) no
N1 C2 C3 C4 . . . . 179.01(15) no
C2 C3 C4 C5 . . . . -0.1(3) no
C2 C3 C4 N2 . . . . -179.55(16) no
C3 C4 C5 C6 . . . . -0.1(3) no
N2 C4 C5 C6 . . . . 179.26(16) no
C3 C4 C5 O1' . . . . 174.3(4) no
N2 C4 C5 O1' . . . . -6.3(5) no
C4 C5 C6 C1 . . . . 1.1(2) no
O1' C5 C6 C1 . . . . -172.5(5) no
C4 C5 C6 N3 . . . . -178.51(15) no
O1' C5 C6 N3 . . . . 7.9(5) no
O1 C1 C6 C5 . . . . 177.14(16) no
C2 C1 C6 C5 . . . . -1.6(2) no
O1 C1 C6 N3 . . . . -3.3(3) no
C2 C1 C6 N3 . . . . 177.95(14) no
N4 C7 C8 C9 . . . . 179.68(12) no
C8 C7 C8 C9 3_655 . . . -0.32(12) no
C7 C8 C9 C10 . . . . 0.6(2) no
C8 C9 C10 C9 . . . 3_655 -0.31(12) no
C8 C9 C10 N5 . . . . 179.68(12) no
C9 C10 N5 O8 . . . 3_655 -175.18(14) no
C9 C10 N5 O8 3_655 . . 3_655 4.82(14) no
C9 C10 N5 O8 . . . . 4.82(14) no
C9 C10 N5 O8 3_655 . . . -175.18(14) no
C3 C2 N1 O2' . . . . 173.0(10) no
C1 C2 N1 O2' . . . . -7.5(10) no
C3 C2 N1 O3 . . . . 24.2(17) no
C1 C2 N1 O3 . . . . -156.3(17) no
C3 C2 N1 O2 . . . . -168.1(6) no
C1 C2 N1 O2 . . . . 11.4(6) no
C3 C2 N1 O3' . . . . -18.2(9) no
C1 C2 N1 O3' . . . . 161.3(9) no
C3 C4 N2 O4 . . . . -2.7(9) no
C5 C4 N2 O4 . . . . 177.9(9) no
C3 C4 N2 O5 . . . . 178.4(6) no
C5 C4 N2 O5 . . . . -1.0(6) no
C3 C4 N2 O4' . . . . 16(2) no
C5 C4 N2 O4' . . . . -163(2) no
C3 C4 N2 O5' . . . . -165(2) no
C5 C4 N2 O5' . . . . 15(2) no
C5 C6 N3 O6 . . . . 1.5(2) no
C1 C6 N3 O6 . . . . -178.11(17) no
C5 C6 N3 O7 . . . . -179.18(17) no
C1 C6 N3 O7 . . . . 1.2(2) no
