#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224105.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_2224105
loop_
_publ_author_name
'Zhang, Qiao-Ling'
'Qu, Xiao-Feng'
'Wang, Jian-Long'
_publ_section_title
;
 (3,5-Dinitro-1,3,5-triazinan-1-yl)methanone
;
_journal_coeditor_code           ZS2012
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2749
_journal_paper_doi               10.1107/S1600536809041531
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H9 N5 O5'
_chemical_formula_moiety         'C5 H9 N5 O5'
_chemical_formula_sum            'C5 H9 N5 O5'
_chemical_formula_weight         219.17
_chemical_melting_point          431(2)
_chemical_name_systematic
;
(3,5-Dinitro-1,3,5-triazinan-1-yl)methanone
;
_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                 100.42(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8972(18)
_cell_length_b                   10.061(2)
_cell_length_c                   9.890(2)
_cell_measurement_reflns_used    3599
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.84
_cell_volume                     870.7(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 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      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3599
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9429
_exptl_absorpt_correction_T_min  0.9294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.257
_refine_ls_extinction_coef       0.242(16)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.09P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                1419
_reflns_number_total             1988
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2012.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224105
_cod_database_fobs_code          2224105
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_disorder_assembly
_atom_site_disorder_group
C C1 0.47469(19) 0.41301(16) 0.32195(16) 0.0389(4) Uani d . 1 . .
H H1A 0.5005 0.3837 0.4168 0.047 Uiso calc R 1 . .
H H1B 0.4000 0.4839 0.3170 0.047 Uiso calc R 1 . .
C C2 0.72467(19) 0.35894(19) 0.26987(18) 0.0456(4) Uani d . 1 . .
H H2A 0.8044 0.3941 0.2248 0.055 Uiso calc R 1 . .
H H2B 0.7713 0.3329 0.3624 0.055 Uiso calc R 1 . .
C C3 0.51659(19) 0.19589(16) 0.23350(19) 0.0429(4) Uani d . 1 . .
H H3A 0.4708 0.1292 0.1680 0.052 Uiso calc R 1 . .
H H3B 0.5392 0.1547 0.3236 0.052 Uiso calc R 1 . .
C C4 0.26587(18) 0.29469(17) 0.16314(15) 0.0385(4) Uani d . 1 . .
C C5 0.1604(2) 0.4079(2) 0.1715(2) 0.0531(5) Uani d . 1 . .
H H5A 0.0627 0.3892 0.1158 0.080 Uiso calc R 1 . .
H H5B 0.2020 0.4873 0.1390 0.080 Uiso calc R 1 . .
H H5C 0.1485 0.4201 0.2653 0.080 Uiso calc R 1 . .
N N1 0.41055(15) 0.30361(13) 0.23592(13) 0.0357(3) Uani d . 1 . .
N N2 0.61111(16) 0.46206(14) 0.27642(13) 0.0405(4) Uani d . 1 . .
N N3 0.65682(16) 0.24375(17) 0.19558(16) 0.0491(4) Uani d . 1 . .
N N4 0.5835(2) 0.54679(16) 0.16262(16) 0.0550(5) Uani d . 1 . .
N N5 0.69287(18) 0.21008(15) 0.07159(15) 0.0468(4) Uani d . 1 . .
O O1 0.6820(2) 0.55437(17) 0.09159(16) 0.0839(6) Uani d . 1 . .
O O2 0.22571(14) 0.19538(13) 0.09572(13) 0.0525(4) Uani d . 1 . .
O O3 0.6163(2) 0.12455(17) 0.00671(15) 0.0723(5) Uani d . 1 . .
O O4 0.80447(17) 0.26203(18) 0.03929(15) 0.0685(5) Uani d . 1 . .
O O5 0.4676(2) 0.61206(16) 0.14783(19) 0.0819(6) 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
N1 C1 N2 . . 109.82(13) ?
N1 C1 H1A . . 109.7 ?
N2 C1 H1A . . 109.7 ?
N1 C1 H1B . . 109.7 ?
N2 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
N3 C2 N2 . . 111.37(13) ?
N3 C2 H2A . . 109.4 ?
N2 C2 H2A . . 109.4 ?
N3 C2 H2B . . 109.4 ?
N2 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
N1 C3 N3 . . 110.59(14) ?
N1 C3 H3A . . 109.5 ?
N3 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
N3 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
O2 C4 N1 . . 119.99(16) ?
O2 C4 C5 . . 122.20(16) ?
N1 C4 C5 . . 117.81(15) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 N1 C3 . . 120.14(13) ?
C4 N1 C1 . . 126.71(14) ?
C3 N1 C1 . . 113.15(13) ?
N4 N2 C1 . . 114.91(14) ?
N4 N2 C2 . . 114.86(15) ?
C1 N2 C2 . . 113.33(13) ?
N5 N3 C2 . . 120.76(15) ?
N5 N3 C3 . . 120.23(15) ?
C2 N3 C3 . . 115.80(14) ?
O5 N4 O1 . . 125.60(18) ?
O5 N4 N2 . . 116.75(17) ?
O1 N4 N2 . . 117.51(19) ?
O3 N5 O4 . . 125.20(17) ?
O3 N5 N3 . . 116.89(16) ?
O4 N5 N3 . . 117.74(16) ?
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 N1 . 1.4440(19) ?
C1 N2 . 1.455(2) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N3 . 1.445(2) ?
C2 N2 . 1.458(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N1 . 1.440(2) ?
C3 N3 . 1.449(2) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O2 . 1.2184(19) ?
C4 N1 . 1.359(2) ?
C4 C5 . 1.487(2) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
N2 N4 . 1.398(2) ?
N3 N5 . 1.365(2) ?
N4 O5 . 1.209(2) ?
N4 O1 . 1.220(2) ?
N5 O3 . 1.208(2) ?
N5 O4 . 1.215(2) ?
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
O2 C4 N1 C3 . . . . 0.0(2) ?
C5 C4 N1 C3 . . . . 178.88(14) ?
O2 C4 N1 C1 . . . . -179.01(15) ?
C5 C4 N1 C1 . . . . -0.2(2) ?
N3 C3 N1 C4 . . . . 126.86(15) ?
N3 C3 N1 C1 . . . . -53.98(18) ?
N2 C1 N1 C4 . . . . -123.74(16) ?
N2 C1 N1 C3 . . . . 57.17(17) ?
N1 C1 N2 N4 . . . . 80.18(16) ?
N1 C1 N2 C2 . . . . -54.65(17) ?
N3 C2 N2 N4 . . . . -85.27(16) ?
N3 C2 N2 C1 . . . . 49.60(18) ?
N2 C2 N3 N5 . . . . 112.60(17) ?
N2 C2 N3 C3 . . . . -47.2(2) ?
N1 C3 N3 N5 . . . . -110.68(18) ?
N1 C3 N3 C2 . . . . 49.2(2) ?
C1 N2 N4 O5 . . . . 28.9(2) ?
C2 N2 N4 O5 . . . . 163.00(15) ?
C1 N2 N4 O1 . . . . -155.26(16) ?
C2 N2 N4 O1 . . . . -21.1(2) ?
C2 N3 N5 O3 . . . . -169.79(16) ?
C3 N3 N5 O3 . . . . -10.9(2) ?
C2 N3 N5 O4 . . . . 14.7(2) ?
C3 N3 N5 O4 . . . . 173.59(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24706
