#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/94/2219414.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_2219414
loop_
_publ_author_name
'Li, Ying'
'Li, Ping'
'Zhou, Qiu-Ping'
'Zhang, Guo-Fang'
'Ng, Seik Weng'
_publ_section_title
;
 3,5-Dinitropyridin-4(1H)-one monohydrate
;
_journal_coeditor_code           PK2110
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1701
_journal_paper_doi               10.1107/S1600536808024604
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C5 H3 N3 O5, H2 O'
_chemical_formula_moiety         'C5 H3 N3 O5, H2 O'
_chemical_formula_sum            'C5 H5 N3 O6'
_chemical_formula_weight         203.12
_chemical_name_systematic
;
3,5-Dinitropyridin-4(1H)-one monohydrate
;
_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            16
_cell_length_a                   21.728(2)
_cell_length_b                   21.654(2)
_cell_length_c                   6.5713(5)
_cell_measurement_reflns_used    6494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.7
_cell_volume                     3091.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21800
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.6904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                2852
_reflns_number_total             3555
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2110.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_original_cell_volume        3091.7(4)
_cod_database_code               2219414
_cod_database_fobs_code          2219414
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
O O1 0.69961(7) 0.46193(6) 0.2892(3) 0.0552(4) Uani d . 1
O O2 0.62136(6) 0.50982(6) 0.4163(3) 0.0464(4) Uani d . 1
O O3 0.60319(6) 0.62125(6) 0.2292(2) 0.0431(4) Uani d . 1
O O4 0.61633(6) 0.73545(6) 0.0695(3) 0.0486(4) Uani d . 1
O O5 0.70310(8) 0.77792(8) 0.1081(6) 0.1176(12) Uani d . 1
O O6 0.60858(6) 0.75858(6) 0.5467(3) 0.0496(4) Uani d . 1
O O7 0.65774(6) 0.67898(7) 0.6579(3) 0.0562(4) Uani d . 1
O O8 0.5000 0.77618(7) 0.7500 0.0389(4) Uani d S 1
O O9 0.65904(7) 0.92189(7) 0.1991(3) 0.0659(5) Uani d . 1
O O10 0.61401(6) 1.00203(6) 0.0759(3) 0.0482(4) Uani d . 1
O O11 0.5000 1.02039(7) 0.2500 0.0357(4) Uani d S 1
O O1W 0.91543(6) 0.62174(6) 0.2293(3) 0.0507(4) Uani d D 1
O O2W 0.5000 0.46255(9) 0.7500 0.0627(7) Uani d SD 1
O O3W 0.5000 0.70522(8) 0.2500 0.0416(5) Uani d SD 1
N N1 0.67114(7) 0.50953(7) 0.3278(3) 0.0360(3) Uani d . 1
N N2 0.67066(7) 0.73271(7) 0.1089(3) 0.0435(4) Uani d . 1
N N3 0.79137(7) 0.61956(8) 0.1992(3) 0.0434(4) Uani d D 1
N N4 0.61008(6) 0.70807(7) 0.6311(3) 0.0357(3) Uani d . 1
N N5 0.5000 0.58686(9) 0.7500 0.0376(5) Uani d SD 1
N N6 0.5000 0.83100(9) 0.2500 0.0384(5) Uani d SD 1
N N7 0.61264(7) 0.95139(7) 0.1582(3) 0.0377(4) Uani d . 1
C C1 0.76100(8) 0.56854(9) 0.2549(3) 0.0390(4) Uani d . 1
H H1A 0.7829 0.5329 0.2857 0.047 Uiso calc R 1
C C2 0.69872(8) 0.56805(8) 0.2672(3) 0.0315(4) Uani d . 1
C C3 0.65995(8) 0.62114(7) 0.2208(3) 0.0302(4) Uani d . 1
C C4 0.69804(8) 0.67347(8) 0.1610(3) 0.0337(4) Uani d . 1
C C5 0.76066(8) 0.67135(9) 0.1539(3) 0.0405(4) Uani d . 1
H H5A 0.7825 0.7065 0.1169 0.049 Uiso calc R 1
C C6 0.55166(8) 0.61756(8) 0.7027(3) 0.0345(4) Uani d . 1
H H6A 0.5874 0.5957 0.6733 0.041 Uiso calc R 1
C C7 0.55244(7) 0.68038(7) 0.6972(3) 0.0290(4) Uani d . 1
C C8 0.5000 0.71922(10) 0.7500 0.0269(5) Uani d S 1
C C9 0.55223(9) 0.86172(8) 0.2128(3) 0.0360(4) Uani d . 1
H H9 0.5884 0.8398 0.1893 0.043 Uiso calc R 1
C C10 0.55324(8) 0.92451(7) 0.2090(3) 0.0301(4) Uani d . 1
C C11 0.5000 0.96327(10) 0.2500 0.0278(5) Uani d S 1
H H11 0.9376(8) 0.6540(6) 0.220(4) 0.059(7) Uiso d D 1
H H12 0.9385(8) 0.5898(6) 0.218(4) 0.053(7) Uiso d D 1
H H21 0.4680(2) 0.4409(7) 0.757(4) 0.055(7) Uiso d D 1
H H31 0.5318(3) 0.6832(7) 0.236(4) 0.058(7) Uiso d D 1
H H3 0.8306(5) 0.6181(10) 0.199(4) 0.057(7) Uiso d D 1
H H5 0.5000 0.5477(5) 0.7500 0.051(9) Uiso d SD 1
H H6 0.5000 0.7915(5) 0.2500 0.051(9) Uiso d SD 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
H11 O1W H12 . . 109.1(14)
O2 N1 O1 . . 123.08(16)
O2 N1 C2 . . 119.15(14)
O1 N1 C2 . . 117.76(15)
O5 N2 O4 . . 121.96(17)
O5 N2 C4 . . 118.53(17)
O4 N2 C4 . . 119.51(15)
C1 N3 C5 . . 120.47(16)
C1 N3 H3 . . 117.6(16)
C5 N3 H3 . . 121.8(16)
O7 N4 O6 . . 123.11(15)
O7 N4 C7 . . 118.20(15)
O6 N4 C7 . . 118.66(14)
C6 N5 C6 . 3_656 120.6(2)
C6 N5 H5 . . 119.71(10)
C6 N5 H5 3_656 . 119.71(10)
C9 N6 C9 . 3_655 120.4(2)
C9 N6 H6 . . 119.82(11)
C9 N6 H6 3_655 . 119.82(10)
O10 N7 O9 . . 123.05(16)
O10 N7 C10 . . 118.79(14)
O9 N7 C10 . . 118.16(16)
N3 C1 C2 . . 120.99(17)
N3 C1 H1A . . 119.5
C2 C1 H1A . . 119.5
C1 C2 N1 . . 115.69(15)
C1 C2 C3 . . 123.94(16)
N1 C2 C3 . . 120.36(14)
O3 C3 C4 . . 125.31(15)
O3 C3 C2 . . 124.72(15)
C4 C3 C2 . . 109.97(14)
C5 C4 N2 . . 115.48(16)
C5 C4 C3 . . 123.38(16)
N2 C4 C3 . . 121.12(15)
N3 C5 C4 . . 121.24(17)
N3 C5 H5A . . 119.4
C4 C5 H5A . . 119.4
N5 C6 C7 . . 120.80(16)
N5 C6 H6A . . 119.6
C7 C6 H6A . . 119.6
C6 C7 N4 . . 115.51(15)
C6 C7 C8 . . 124.09(16)
N4 C7 C8 . . 120.39(14)
O8 C8 C7 . 3_656 125.23(9)
O8 C8 C7 . . 125.23(9)
C7 C8 C7 3_656 . 109.54(19)
N6 C9 C10 . . 120.94(17)
N6 C9 H9 . . 119.5
C10 C9 H9 . . 119.5
C9 C10 C11 . . 124.11(16)
C9 C10 N7 . . 114.74(15)
C11 C10 N7 . . 121.15(14)
O11 C11 C10 . 3_655 125.25(9)
O11 C11 C10 . . 125.25(9)
C10 C11 C10 3_655 . 109.50(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N1 . 1.2285(19)
O2 N1 . 1.228(2)
O3 C3 . 1.235(2)
O4 N2 . 1.210(2)
O5 N2 . 1.206(2)
O6 N4 . 1.227(2)
O7 N4 . 1.225(2)
O8 C8 . 1.233(3)
O9 N7 . 1.223(2)
O10 N7 . 1.223(2)
O11 C11 . 1.237(3)
O1W H11 . 0.851(9)
O1W H12 . 0.858(9)
O2W H21 . 0.840(8)
O3W H31 . 0.844(8)
N1 C2 . 1.457(2)
N2 C4 . 1.455(2)
N3 C1 . 1.338(3)
N3 C5 . 1.338(3)
N3 H3 . 0.853(10)
N4 C7 . 1.455(2)
N5 C6 . 1.341(2)
N5 C6 3_656 1.341(2)
N5 H5 . 0.848(10)
N6 C9 . 1.338(2)
N6 C9 3_655 1.338(2)
N6 H6 . 0.854(10)
N7 C10 . 1.455(2)
C1 C2 . 1.356(2)
C1 H1A . 0.9300
C2 C3 . 1.457(2)
C3 C4 . 1.457(2)
C4 C5 . 1.362(2)
C5 H5A . 0.9300
C6 C7 . 1.361(2)
C6 H6A . 0.9300
C7 C8 . 1.458(2)
C8 C7 3_656 1.458(2)
C9 C10 . 1.360(2)
C9 H9 . 0.9300
C10 C11 . 1.454(2)
C11 C10 3_655 1.454(2)
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
N3 H3 O1w . 0.850(10) 1.860(10) 2.703(2) 172(2) yes
N5 H5 O2w . 0.850(10) 1.840(10) 2.692(3) 180 yes
N6 H6 O3w . 0.850(10) 1.870(10) 2.723(3) 180 yes
O1w H11 O8 2_664 0.850(10) 2.040(10) 2.878(2) 168(2) yes
O1w H12 O11 6_656 0.860(10) 2.020(10) 2.866(2) 168(2) yes
O2w H21 O3 5_666 0.840(10) 2.050(10) 2.888(2) 173.0(10) yes
O3w H31 O3 . 0.840(10) 2.050(10) 2.890(2) 172(2) 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_4
_geom_torsion
C5 N3 C1 C2 . . -0.1(3)
N3 C1 C2 N1 . . 179.48(18)
N3 C1 C2 C3 . . 0.5(3)
O2 N1 C2 C1 . . 152.19(18)
O1 N1 C2 C1 . . -27.0(3)
O2 N1 C2 C3 . . -28.8(3)
O1 N1 C2 C3 . . 151.95(18)
C1 C2 C3 O3 . . 179.23(19)
N1 C2 C3 O3 . . 0.3(3)
C1 C2 C3 C4 . . -0.1(3)
N1 C2 C3 C4 . . -179.00(16)
O5 N2 C4 C5 . . -16.1(3)
O4 N2 C4 C5 . . 164.46(19)
O5 N2 C4 C3 . . 162.5(3)
O4 N2 C4 C3 . . -16.9(3)
O3 C3 C4 C5 . . 179.9(2)
C2 C3 C4 C5 . . -0.7(3)
O3 C3 C4 N2 . . 1.4(3)
C2 C3 C4 N2 . . -179.23(17)
C1 N3 C5 C4 . . -0.7(3)
N2 C4 C5 N3 . . 179.75(19)
C3 C4 C5 N3 . . 1.2(3)
C6 N5 C6 C7 3_656 . -1.47(13)
N5 C6 C7 N4 . . -176.15(14)
N5 C6 C7 C8 . . 3.0(3)
O7 N4 C7 C6 . . -26.7(2)
O6 N4 C7 C6 . . 151.55(18)
O7 N4 C7 C8 . . 154.12(15)
O6 N4 C7 C8 . . -27.7(2)
C6 C7 C8 O8 . . 178.50(13)
N4 C7 C8 O8 . . -2.34(18)
C6 C7 C8 C7 . 3_656 -1.50(13)
N4 C7 C8 C7 . 3_656 177.66(18)
C9 N6 C9 C10 3_655 . -0.98(13)
N6 C9 C10 C11 . . 2.0(3)
N6 C9 C10 N7 . . -177.52(15)
O10 N7 C10 C9 . . 152.08(18)
O9 N7 C10 C9 . . -27.5(3)
O10 N7 C10 C11 . . -27.5(2)
O9 N7 C10 C11 . . 152.96(17)
C9 C10 C11 O11 . . 179.01(13)
N7 C10 C11 O11 . . -1.48(19)
C9 C10 C11 C10 . 3_655 -0.99(13)
N7 C10 C11 C10 . 3_655 178.52(19)
