#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:33:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180085 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/31/7053181.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7053181
loop_
_publ_author_name
'Hou, Kehui'
'Ma, Congming'
'Liu, Zuliang'
_publ_section_title
;
 Synthesis, single crystal structure and performance of N-substituted
 derivatives of dinitroimidazole
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2837
_journal_paper_doi               10.1039/c3nj00521f
_journal_volume                  37
_journal_year                    2013
_chemical_formula_sum            'C9 H5 N9 O10'
_chemical_formula_weight         399.22
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0830(18)
_cell_length_b                   11.395(2)
_cell_length_c                   14.089(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1439.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2814
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9511
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0505
_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)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                1747
_reflns_number_total             2639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00521f.txt
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/N
_cod_database_code               7053181
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.0882(3) 0.32215(19) 0.57882(16) 0.0366(6) Uani 1 1 d .
C1 C 0.0343(3) 0.2924(2) 0.66686(17) 0.0288(6) Uani 1 1 d .
O1 O 0.2144(3) 0.29183(19) 0.56980(16) 0.0616(7) Uani 1 1 d .
O2 O 0.0106(3) 0.37623(19) 0.51617(14) 0.0582(6) Uani 1 1 d .
C2 C -0.0798(3) 0.3626(2) 0.69853(19) 0.0361(6) Uani 1 1 d .
N2 N -0.1299(3) 0.4574(2) 0.64997(19) 0.0613(8) Uani 1 1 d .
H2A H -0.1955 0.5011 0.6704 0.074 Uiso 1 1 calc R
H2B H -0.0970 0.4755 0.5979 0.074 Uiso 1 1 calc R
N3 N -0.2378(3) 0.3990(2) 0.82302(19) 0.0444(6) Uani 1 1 d .
O3 O -0.2955(3) 0.4823(2) 0.77693(19) 0.0798(8) Uani 1 1 d .
C3 C -0.1296(3) 0.3275(2) 0.78528(18) 0.0339(6) Uani 1 1 d .
N4 N -0.1332(3) 0.1836(2) 0.91097(16) 0.0462(7) Uani 1 1 d .
H4A H -0.2049 0.2205 0.9309 0.055 Uiso 1 1 calc R
H4B H -0.0980 0.1205 0.9396 0.055 Uiso 1 1 calc R
C4 C -0.0770(3) 0.2237(2) 0.83624(18) 0.0327(6) Uani 1 1 d .
O4 O -0.2714(3) 0.3775(2) 0.90207(16) 0.0653(7) Uani 1 1 d .
C5 C 0.0426(3) 0.1628(2) 0.80279(18) 0.0331(6) Uani 1 1 d .
N5 N 0.1172(3) 0.0666(2) 0.85878(17) 0.0450(6) Uani 1 1 d .
O5 O 0.0443(3) 0.0035(2) 0.90501(18) 0.0756(8) Uani 1 1 d .
N6 N 0.1909(2) 0.11765(18) 0.67963(15) 0.0311(5) Uani 1 1 d .
C6 C 0.0927(3) 0.1965(2) 0.71944(18) 0.0287(6) Uani 1 1 d .
O6 O 0.2495(3) 0.0517(2) 0.85854(17) 0.0660(7) Uani 1 1 d .
N7 N 0.3921(3) 0.0369(2) 0.63335(17) 0.0413(6) Uani 1 1 d .
C7 C 0.1398(3) 0.0263(2) 0.62099(18) 0.0328(6) Uani 1 1 d .
H7B H 0.0418 0.0012 0.6034 0.039 Uiso 1 1 calc R
O7 O 0.5668(3) 0.2020(2) 0.7361(2) 0.0831(9) Uani 1 1 d .
C8 C 0.2650(3) -0.0196(2) 0.59420(19) 0.0354(6) Uani 1 1 d .
O8 O 0.3726(2) 0.2803(2) 0.77933(17) 0.0661(7) Uani 1 1 d .
N8 N 0.4349(3) 0.2065(2) 0.73729(19) 0.0502(7) Uani 1 1 d .
C9 C 0.3420(3) 0.1190(2) 0.68355(19) 0.0362(7) Uani 1 1 d .
N9 N 0.2683(3) -0.1151(2) 0.52812(17) 0.0465(6) Uani 1 1 d .
O9 O 0.1469(3) -0.1517(2) 0.48981(18) 0.0676(7) Uani 1 1 d .
O10 O 0.3868(3) -0.1525(2) 0.51289(18) 0.0764(8) Uani 1 1 d .
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
O2 N1 O1 121.0(2)
O2 N1 C1 120.6(2)
O1 N1 C1 118.4(2)
C6 C1 C2 120.6(2)
C6 C1 N1 119.6(2)
C2 C1 N1 119.8(2)
N2 C2 C3 122.9(3)
N2 C2 C1 120.1(2)
C3 C2 C1 117.0(2)
C2 N2 H2A 120.0
C2 N2 H2B 120.0
H2A N2 H2B 120.0
O3 N3 O4 119.4(3)
O3 N3 C3 120.2(2)
O4 N3 C3 120.4(3)
C4 C3 C2 122.6(2)
C4 C3 N3 118.4(2)
C2 C3 N3 119.0(2)
C4 N4 H4A 120.0
C4 N4 H4B 120.0
H4A N4 H4B 120.0
N4 C4 C3 123.2(2)
N4 C4 C5 120.3(2)
C3 C4 C5 116.5(2)
C6 C5 C4 121.1(2)
C6 C5 N5 118.9(2)
C4 C5 N5 120.0(2)
O6 N5 O5 122.4(3)
O6 N5 C5 118.6(2)
O5 N5 C5 118.9(3)
C7 N6 C9 106.0(2)
C7 N6 C6 122.7(2)
C9 N6 C6 131.1(2)
C1 C6 C5 121.8(2)
C1 C6 N6 119.6(2)
C5 C6 N6 117.8(2)
C9 N7 C8 102.3(2)
C8 C7 N6 104.1(2)
C8 C7 H7B 127.9
N6 C7 H7B 127.9
C7 C8 N7 113.5(2)
C7 C8 N9 125.2(3)
N7 C8 N9 121.2(2)
O7 N8 O8 125.3(3)
O7 N8 C9 117.7(3)
O8 N8 C9 117.0(2)
N7 C9 N6 114.1(2)
N7 C9 N8 123.9(3)
N6 C9 N8 122.0(2)
O10 N9 O9 124.6(3)
O10 N9 C8 119.6(3)
O9 N9 C8 115.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.207(3)
N1 O1 1.223(3)
N1 C1 1.445(3)
C1 C6 1.378(3)
C1 C2 1.436(3)
C2 N2 1.320(3)
C2 C3 1.427(4)
N2 H2A 0.8600
N2 H2B 0.8600
N3 O3 1.220(3)
N3 O4 1.226(3)
N3 C3 1.443(3)
C3 C4 1.425(4)
N4 C4 1.323(3)
N4 H4A 0.8600
N4 H4B 0.8600
C4 C5 1.432(4)
C5 C6 1.380(3)
C5 N5 1.454(3)
N5 O6 1.214(3)
N5 O5 1.232(3)
N6 C7 1.363(3)
N6 C9 1.365(3)
N6 C6 1.441(3)
N7 C9 1.299(3)
N7 C8 1.359(3)
C7 C8 1.359(4)
C7 H7B 0.9300
O7 N8 1.202(3)
C8 N9 1.436(3)
O8 N8 1.219(3)
N8 C9 1.440(4)
N9 O10 1.209(3)
N9 O9 1.221(3)
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
O2 N1 C1 C6 154.6(2)
O1 N1 C1 C6 -25.8(4)
O2 N1 C1 C2 -25.1(4)
O1 N1 C1 C2 154.4(2)
C6 C1 C2 N2 176.8(3)
N1 C1 C2 N2 -3.4(4)
C6 C1 C2 C3 -0.6(4)
N1 C1 C2 C3 179.1(2)
N2 C2 C3 C4 178.7(3)
C1 C2 C3 C4 -3.9(4)
N2 C2 C3 N3 -0.9(4)
C1 C2 C3 N3 176.5(2)
O3 N3 C3 C4 -173.2(3)
O4 N3 C3 C4 7.6(4)
O3 N3 C3 C2 6.5(4)
O4 N3 C3 C2 -172.7(3)
C2 C3 C4 N4 -172.8(3)
N3 C3 C4 N4 6.9(4)
C2 C3 C4 C5 7.4(4)
N3 C3 C4 C5 -172.9(2)
N4 C4 C5 C6 173.5(2)
C3 C4 C5 C6 -6.7(4)
N4 C4 C5 N5 -8.8(4)
C3 C4 C5 N5 171.0(2)
C6 C5 N5 O6 31.3(4)
C4 C5 N5 O6 -146.4(3)
C6 C5 N5 O5 -149.0(3)
C4 C5 N5 O5 33.3(4)
C2 C1 C6 C5 1.3(4)
N1 C1 C6 C5 -178.5(2)
C2 C1 C6 N6 171.0(2)
N1 C1 C6 N6 -8.7(4)
C4 C5 C6 C1 2.6(4)
N5 C5 C6 C1 -175.1(2)
C4 C5 C6 N6 -167.4(2)
N5 C5 C6 N6 14.9(4)
C7 N6 C6 C1 -86.0(3)
C9 N6 C6 C1 88.7(3)
C7 N6 C6 C5 84.2(3)
C9 N6 C6 C5 -101.1(3)
C9 N6 C7 C8 -0.2(3)
C6 N6 C7 C8 175.7(2)
N6 C7 C8 N7 0.6(3)
N6 C7 C8 N9 -176.9(2)
C9 N7 C8 C7 -0.8(3)
C9 N7 C8 N9 176.8(2)
C8 N7 C9 N6 0.7(3)
C8 N7 C9 N8 -177.9(3)
C7 N6 C9 N7 -0.3(3)
C6 N6 C9 N7 -175.7(2)
C7 N6 C9 N8 178.3(2)
C6 N6 C9 N8 2.9(4)
O7 N8 C9 N7 -0.8(4)
O8 N8 C9 N7 178.2(3)
O7 N8 C9 N6 -179.3(3)
O8 N8 C9 N6 -0.3(4)
C7 C8 N9 O10 -176.5(3)
N7 C8 N9 O10 6.1(4)
C7 C8 N9 O9 4.5(4)
N7 C8 N9 O9 -172.9(3)
