#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/54/2205499.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_2205499
loop_
_publ_author_name
'Jan Lokaj '
'Viktor Kettmann '
'Viktor Milata '
'Milan Marko '
_publ_section_title
;
 4,4-Dinitro-5,6,7,8,9,10-hexahydro-4H-cyclonona[d]isoxazole
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o808
_journal_page_last               o810
_journal_paper_doi               10.1107/S1600536805004186
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H13 N3 O5'
_chemical_formula_moiety         'C10 H13 N3 O5'
_chemical_formula_sum            'C10 H13 N3 O5'
_chemical_formula_weight         255.23
_chemical_melting_point          375
_chemical_name_systematic
;
4,4-Dinitro-5,6,7,8,9,10-hexahydro-4H-cyclonona[d]isoxazole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 113.81(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.735(2)
_cell_length_b                   16.569(4)
_cell_length_c                   8.764(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      7
_cell_volume                     1160.5(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'PLUTON (Spek, 1992)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_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  0.0389
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3583
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0694P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                1421
_reflns_number_total             3383
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6133.cif
_cod_data_source_block           II
_cod_original_cell_volume        1160.5(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205499
_cod_database_fobs_code          2205499
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_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_type_symbol
O1 0.9096(2) -0.05376(10) -0.2294(2) 0.0662(5) Uani d . 1 O
N2 0.7924(3) -0.09898(12) -0.1923(3) 0.0718(6) Uani d . 1 N
C3 0.6943(3) -0.04550(14) -0.1733(3) 0.0594(6) Uani d . 1 C
H3 0.6042 -0.0582 -0.1469 0.071 Uiso calc R 1 H
C3A 0.7373(2) 0.03438(12) -0.1966(2) 0.0427(5) Uani d . 1 C
C4 0.6522(2) 0.10938(12) -0.1786(2) 0.0427(5) Uani d . 1 C
C5 0.6752(3) 0.18516(14) -0.2641(3) 0.0582(6) Uani d . 1 C
H5A 0.7936 0.1976 -0.2231 0.070 Uiso calc R 1 H
H5B 0.6204 0.2299 -0.2352 0.070 Uiso calc R 1 H
C6 0.6041(4) 0.1769(3) -0.4540(4) 0.1237(16) Uani d . 1 C
H6A 0.5645 0.1217 -0.4790 0.148 Uiso calc R 1 H
H6B 0.5056 0.2110 -0.4975 0.148 Uiso calc R 1 H
C7 0.6907(6) 0.1922(4) -0.5451(4) 0.175(3) Uani d . 1 C
H7A 0.6624 0.2471 -0.5846 0.211 Uiso calc R 1 H
H7B 0.6425 0.1579 -0.6427 0.211 Uiso calc R 1 H
C8 0.8713(5) 0.18582(18) -0.4916(4) 0.0915(10) Uani d . 1 C
H8A 0.9233 0.2216 -0.3970 0.110 Uiso calc R 1 H
H8B 0.8988 0.2063 -0.5811 0.110 Uiso calc R 1 H
C9 0.9512(3) 0.10494(16) -0.4434(3) 0.0662(7) Uani d . 1 C
H9A 1.0527 0.1045 -0.4632 0.079 Uiso calc R 1 H
H9B 0.8762 0.0649 -0.5166 0.079 Uiso calc R 1 H
C10 0.9959(3) 0.07882(17) -0.2630(3) 0.0644(7) Uani d . 1 C
H10A 1.1027 0.0511 -0.2236 0.077 Uiso calc R 1 H
H10B 1.0113 0.1271 -0.1958 0.077 Uiso calc R 1 H
C10A 0.8748(3) 0.02586(14) -0.2312(2) 0.0479(5) Uani d . 1 C
N3 0.7033(2) 0.12410(13) 0.0101(2) 0.0566(5) Uani d . 1 N
O2 0.7829(3) 0.18347(12) 0.0707(2) 0.0890(6) Uani d . 1 O
O3 0.6669(2) 0.07114(12) 0.0864(2) 0.0804(6) Uani d . 1 O
N4 0.4612(2) 0.09592(12) -0.2430(3) 0.0584(5) Uani d . 1 N
O4 0.3978(2) 0.04630(11) -0.3503(2) 0.0764(6) Uani d . 1 O
O5 0.3870(2) 0.13998(12) -0.1852(3) 0.0970(7) Uani d . 1 O
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
_geom_angle_publ_flag
C10A O1 N2 109.97(16) yes
C3 N2 O1 104.29(19) yes
N2 C3 C3A 113.3(2) yes
N2 C3 H3 123.3 ?
C3A C3 H3 123.3 ?
C10A C3A C3 104.18(19) yes
C10A C3A C4 129.34(19) ?
C3 C3A C4 126.43(18) ?
C3A C4 C5 117.88(17) ?
C3A C4 N4 110.61(16) ?
C5 C4 N4 106.14(17) ?
C3A C4 N3 107.67(16) ?
C5 C4 N3 111.01(17) ?
N4 C4 N3 102.45(16) ?
C4 C5 C6 112.7(2) ?
C4 C5 H5A 109.0 ?
C6 C5 H5A 109.0 ?
C4 C5 H5B 109.0 ?
C6 C5 H5B 109.0 ?
H5A C5 H5B 107.8 ?
C7 C6 C5 123.9(3) ?
C7 C6 H6A 106.4 ?
C5 C6 H6A 106.4 ?
C7 C6 H6B 106.4 ?
C5 C6 H6B 106.4 ?
H6A C6 H6B 106.4 ?
C6 C7 C8 126.8(3) ?
C6 C7 H7A 105.6 ?
C8 C7 H7A 105.6 ?
C6 C7 H7B 105.6 ?
C8 C7 H7B 105.6 ?
H7A C7 H7B 106.1 ?
C7 C8 C9 118.6(3) ?
C7 C8 H8A 107.7 ?
C9 C8 H8A 107.7 ?
C7 C8 H8B 107.7 ?
C9 C8 H8B 107.7 ?
H8A C8 H8B 107.1 ?
C8 C9 C10 116.2(2) ?
C8 C9 H9A 108.2 ?
C10 C9 H9A 108.2 ?
C8 C9 H9B 108.2 ?
C10 C9 H9B 108.2 ?
H9A C9 H9B 107.4 ?
C10A C10 C9 117.2(2) ?
C10A C10 H10A 108.0 ?
C9 C10 H10A 108.0 ?
C10A C10 H10B 108.0 ?
C9 C10 H10B 108.0 ?
H10A C10 H10B 107.2 ?
O1 C10A C3A 108.2(2) yes
O1 C10A C10 113.95(19) ?
C3A C10A C10 137.8(2) ?
O2 N3 O3 125.5(2) ?
O2 N3 C4 117.92(19) ?
O3 N3 C4 116.43(19) ?
O4 N4 O5 125.6(2) ?
O4 N4 C4 118.16(18) ?
O5 N4 C4 116.09(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10A 1.352(3) yes
O1 N2 1.408(3) yes
N2 C3 1.289(3) yes
C3 C3A 1.413(3) yes
C3 H3 0.9300 ?
C3A C10A 1.360(3) yes
C3A C4 1.489(3) ?
C4 C5 1.516(3) ?
C4 N4 1.547(3) yes
C4 N3 1.549(3) yes
C5 C6 1.530(4) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.327(5) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.457(5) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.491(4) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.530(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C10A 1.484(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
N3 O2 1.198(2) yes
N3 O3 1.220(2) yes
N4 O4 1.202(2) yes
N4 O5 1.214(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
C10A O1 N2 C3 -0.2(3)
O1 N2 C3 C3A 0.4(3)
N2 C3 C3A C10A -0.5(3)
N2 C3 C3A C4 -178.1(2)
C10A C3A C4 C5 23.7(3)
C3 C3A C4 C5 -159.3(2)
C10A C3A C4 N4 146.1(2)
C3 C3A C4 N4 -37.0(3)
C10A C3A C4 N3 -102.7(2)
C3 C3A C4 N3 74.2(3)
C3A C4 C5 C6 63.0(3)
N4 C4 C5 C6 -61.6(3)
N3 C4 C5 C6 -172.2(2)
C4 C5 C6 C7 -127.1(5)
C5 C6 C7 C8 27.7(9)
C6 C7 C8 C9 63.6(7)
C7 C8 C9 C10 -85.1(3)
C8 C9 C10 C10A 96.9(3)
N2 O1 C10A C3A -0.1(2)
N2 O1 C10A C10 177.79(17)
C3 C3A C10A O1 0.3(2)
C4 C3A C10A O1 177.83(19)
C3 C3A C10A C10 -176.8(2)
C4 C3A C10A C10 0.7(4)
C9 C10 C10A O1 94.6(2)
C9 C10 C10A C3A -88.4(3)
C3A C4 N3 O2 115.7(2)
C5 C4 N3 O2 -14.7(3)
N4 C4 N3 O2 -127.6(2)
C3A C4 N3 O3 -60.1(2)
C5 C4 N3 O3 169.55(19)
N4 C4 N3 O3 56.6(2)
C3A C4 N4 O4 -28.1(3)
C5 C4 N4 O4 100.9(2)
N3 C4 N4 O4 -142.6(2)
C3A C4 N4 O5 155.4(2)
C5 C4 N4 O5 -75.6(2)
N3 C4 N4 O5 40.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24733718
