#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230560.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_2230560
loop_
_publ_author_name
'Li, Yong-Xiang'
'Du, Shan'
'Wang, Jian-Long'
_publ_section_title
;
 3,4-Dinitro-1H-pyrazole benzene 0.25-solvate
;
_journal_coeditor_code           ZS2110
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1369
_journal_paper_doi               10.1107/S1600536811015996
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C3 H2 N4 O4, 0.5C6 H6'
_chemical_formula_moiety         '2(C3 H2 N4 O4), 0.5(C6 H6)'
_chemical_formula_sum            'C9 H7 N8 O8'
_chemical_formula_weight         355.23
_chemical_name_common            '3,4-dinitropyrazole benzene 0.25-solvate'
_chemical_name_systematic
;
3,4-Dinitro-1H-pyrazole benzene 0.25-solvate
;
_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                 94.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4579(15)
_cell_length_b                   9.787(2)
_cell_length_c                   19.534(4)
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.09
_cell_volume                     1420.6(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0839
_diffrn_reflns_av_sigmaI/netI    0.1445
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3256
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.328
_refine_ls_extinction_coef       0.0081(6)
_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   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0601
_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)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                1267
_reflns_number_total             3256
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2110.cif
_cod_data_source_block           I
_cod_original_cell_volume        1420.7(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230560
_cod_database_fobs_code          2230560
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9887(4) 0.1907(3) 0.19586(16) 0.0327(8) Uani d . 1 1 . .
C C2 1.1357(4) 0.1088(4) 0.19047(17) 0.0420(9) Uani d . 1 1 . .
H H2 1.2585 0.1359 0.1953 0.050 Uiso calc R 1 1 . .
C C3 0.8410(4) 0.1014(3) 0.18468(16) 0.0289(8) Uani d . 1 1 . .
C C4 0.5086(4) 0.5510(3) 0.09984(17) 0.0387(9) Uani d . 1 1 . .
C C5 0.3685(4) 0.6383(3) 0.11466(16) 0.0344(8) Uani d . 1 1 . .
C C6 0.6606(4) 0.6268(4) 0.10959(18) 0.0538(11) Uani d . 1 1 . .
H H6 0.7801 0.5975 0.1045 0.065 Uiso calc R 1 1 . .
C C7 1.1648(8) 0.0615(7) 0.0108(2) 0.0902(16) Uani d . 1 1 . .
H H7 1.2790 0.1045 0.0180 0.108 Uiso calc R 1 1 . .
C C8 1.0067(11) 0.1372(5) 0.0150(2) 0.0921(19) Uani d . 1 1 . .
H H8 1.0132 0.2318 0.0258 0.111 Uiso calc R 1 1 . .
C C9 0.8469(8) 0.0760(7) 0.0040(2) 0.0880(17) Uani d . 1 1 . .
H H9 0.7399 0.1279 0.0063 0.106 Uiso calc R 1 1 . .
N N1 0.9970(4) 0.3361(3) 0.20565(14) 0.0409(7) Uani d . 1 1 . .
N N2 0.6477(3) 0.1259(3) 0.18791(15) 0.0431(8) Uani d . 1 1 . .
N N3 1.0721(3) -0.0172(3) 0.17704(15) 0.0415(8) Uani d D 1 1 . .
N N4 0.8896(3) -0.0246(3) 0.17325(13) 0.0364(7) Uani d . 1 1 . .
N N5 0.5049(4) 0.4072(3) 0.08235(17) 0.0540(9) Uani d . 1 1 . .
N N6 0.1748(3) 0.6197(3) 0.10954(15) 0.0422(7) Uani d . 1 1 . .
N N7 0.6079(4) 0.7520(4) 0.12796(17) 0.0533(9) Uani d D 1 1 . .
N N8 0.4295(3) 0.7621(3) 0.13217(14) 0.0455(8) Uani d . 1 1 . .
O O1 1.1467(3) 0.3853(3) 0.22096(13) 0.0593(8) Uani d . 1 1 . .
O O2 0.8580(3) 0.4027(3) 0.19682(14) 0.0638(8) Uani d . 1 1 . .
O O3 0.6020(3) 0.2140(3) 0.22658(13) 0.0616(8) Uani d . 1 1 . .
O O4 0.5471(3) 0.0518(3) 0.15166(14) 0.0585(8) Uani d . 1 1 . .
O O5 0.6340(4) 0.3642(3) 0.05424(15) 0.0840(10) Uani d . 1 1 . .
O O6 0.3762(4) 0.3390(3) 0.09674(17) 0.0864(10) Uani d . 1 1 . .
O O7 0.1130(3) 0.5307(3) 0.07052(13) 0.0636(8) Uani d . 1 1 . .
O O8 0.0861(3) 0.6953(3) 0.14284(14) 0.0631(8) Uani d . 1 1 . .
H H7A 0.684(5) 0.820(4) 0.127(3) 0.17(2) Uiso d D 1 1 . .
H H3 1.138(3) -0.091(2) 0.1735(17) 0.052(11) Uiso d D 1 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
C2 C1 C3 . . 104.2(3) ?
C2 C1 N1 . . 124.3(3) ?
C3 C1 N1 . . 131.3(3) ?
N3 C2 C1 . . 106.3(3) ?
N3 C2 H2 . . 126.8 ?
C1 C2 H2 . . 126.8 ?
N4 C3 C1 . . 112.7(3) ?
N4 C3 N2 . . 116.7(3) ?
C1 C3 N2 . . 130.5(3) ?
C6 C4 C5 . . 105.5(3) ?
C6 C4 N5 . . 124.4(3) ?
C5 C4 N5 . . 130.0(3) ?
N8 C5 C4 . . 111.4(3) ?
N8 C5 N6 . . 116.7(3) ?
C4 C5 N6 . . 131.7(3) ?
N7 C6 C4 . . 106.1(3) ?
N7 C6 H6 . . 127.0 ?
C4 C6 H6 . . 127.0 ?
C9 C7 C8 3_755 . 119.4(5) ?
C9 C7 H7 3_755 . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 119.8(5) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C7 . 3_755 120.8(5) ?
C8 C9 H9 . . 119.6 ?
C7 C9 H9 3_755 . 119.6 ?
O2 N1 O1 . . 124.5(3) ?
O2 N1 C1 . . 118.8(3) ?
O1 N1 C1 . . 116.6(3) ?
O3 N2 O4 . . 126.1(3) ?
O3 N2 C3 . . 118.1(3) ?
O4 N2 C3 . . 115.7(3) ?
C2 N3 N4 . . 113.3(3) ?
C2 N3 H3 . . 125(2) ?
N4 N3 H3 . . 121(2) ?
C3 N4 N3 . . 103.4(3) ?
O6 N5 O5 . . 125.4(3) ?
O6 N5 C4 . . 118.5(3) ?
O5 N5 C4 . . 116.1(3) ?
O8 N6 O7 . . 125.0(3) ?
O8 N6 C5 . . 118.0(3) ?
O7 N6 C5 . . 117.0(3) ?
N8 N7 C6 . . 113.4(3) ?
N8 N7 H7A . . 126(3) ?
C6 N7 H7A . . 119(3) ?
C5 N8 N7 . . 103.7(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 C2 . 1.370(4) ?
C1 C3 . 1.409(4) ?
C1 N1 . 1.436(4) ?
C2 N3 . 1.339(4) ?
C2 H2 . 0.9500 ?
C3 N4 . 1.310(4) ?
C3 N2 . 1.468(3) ?
C4 C6 . 1.355(4) ?
C4 C5 . 1.398(4) ?
C4 N5 . 1.448(4) ?
C5 N8 . 1.328(4) ?
C5 N6 . 1.451(4) ?
C6 N7 . 1.344(4) ?
C6 H6 . 0.9500 ?
C7 C9 3_755 1.377(7) ?
C7 C8 . 1.401(7) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.335(7) ?
C8 H8 . 0.9500 ?
C9 C7 3_755 1.377(7) ?
C9 H9 . 0.9500 ?
N1 O2 . 1.224(3) ?
N1 O1 . 1.229(3) ?
N2 O3 . 1.214(3) ?
N2 O4 . 1.225(3) ?
N3 N4 . 1.359(3) ?
N3 H3 . 0.876(10) ?
N5 O6 . 1.221(4) ?
N5 O5 . 1.223(4) ?
N6 O8 . 1.217(3) ?
N6 O7 . 1.222(3) ?
N7 N8 . 1.344(4) ?
N7 H7A . 0.878(10) ?
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
C3 C1 C2 N3 . . . . 0.1(4) ?
N1 C1 C2 N3 . . . . -175.8(3) ?
C2 C1 C3 N4 . . . . -0.1(4) ?
N1 C1 C3 N4 . . . . 175.4(3) ?
C2 C1 C3 N2 . . . . 175.9(3) ?
N1 C1 C3 N2 . . . . -8.6(6) ?
C6 C4 C5 N8 . . . . 0.5(4) ?
N5 C4 C5 N8 . . . . 176.4(4) ?
C6 C4 C5 N6 . . . . 175.6(3) ?
N5 C4 C5 N6 . . . . -8.5(6) ?
C5 C4 C6 N7 . . . . -1.0(4) ?
N5 C4 C6 N7 . . . . -177.2(3) ?
C9 C7 C8 C9 3_755 . . . -0.8(8) ?
C7 C8 C9 C7 . . . 3_755 0.8(9) ?
C2 C1 N1 O2 . . . . 166.3(3) ?
C3 C1 N1 O2 . . . . -8.5(6) ?
C2 C1 N1 O1 . . . . -12.0(5) ?
C3 C1 N1 O1 . . . . 173.2(3) ?
N4 C3 N2 O3 . . . . 146.8(3) ?
C1 C3 N2 O3 . . . . -29.0(5) ?
N4 C3 N2 O4 . . . . -31.6(4) ?
C1 C3 N2 O4 . . . . 152.5(3) ?
C1 C2 N3 N4 . . . . -0.1(4) ?
C1 C3 N4 N3 . . . . 0.0(4) ?
N2 C3 N4 N3 . . . . -176.6(3) ?
C2 N3 N4 C3 . . . . 0.1(4) ?
C6 C4 N5 O6 . . . . 155.9(4) ?
C5 C4 N5 O6 . . . . -19.3(6) ?
C6 C4 N5 O5 . . . . -23.7(5) ?
C5 C4 N5 O5 . . . . 161.0(3) ?
N8 C5 N6 O8 . . . . -25.2(4) ?
C4 C5 N6 O8 . . . . 159.9(3) ?
N8 C5 N6 O7 . . . . 153.1(3) ?
C4 C5 N6 O7 . . . . -21.8(5) ?
C4 C6 N7 N8 . . . . 1.2(4) ?
C4 C5 N8 N7 . . . . 0.3(4) ?
N6 C5 N8 N7 . . . . -175.7(3) ?
C6 N7 N8 C5 . . . . -0.9(4) ?
