#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008339.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_2008339
loop_
_publ_author_name
'Yoshihara, Ryouko'
'Hosomi, Hiroyuki'
'Aoyama, Hiromu'
'Ohba, Shigeru'
_publ_section_title
;
 N-Propylimidazolidinetrione and
 N-methyl-N'-phenylethylimidazolidinetrione
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              594
_journal_page_last               596
_journal_paper_doi               10.1107/S0108270198017600
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C6 H8 N2 O3'
_chemical_formula_sum            'C6 H8 N2 O3'
_chemical_formula_weight         156.14
_chemical_name_common            N-propylimidazolidinetrion
_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'
_cell_angle_alpha                90
_cell_angle_beta                 99.86(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.503(4)
_cell_length_b                   4.975(2)
_cell_length_c                   13.304(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.6
_cell_volume                     750.1(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1998)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2829
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         32.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00226|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                1549
_reflns_number_total             2715
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            da1052.cif
_cod_data_source_block           I
_cod_original_cell_volume        750.2(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C6 H8 N2 O3 '
_cod_database_code               2008339
_cod_database_fobs_code          2008339
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
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_occupancy
_atom_site_type_symbol
O1 -0.03304(10) 0.5487(2) 0.62965(8) 0.0413(3) Uani 1.00 O
O2 0.20250(10) -0.1512(3) 0.57090(10) 0.0501(3) Uani 1.00 O
O3 0.16610(10) -0.1680(2) 0.78845(9) 0.0454(3) Uani 1.00 O
N4 0.08440(10) 0.2257(2) 0.57249(9) 0.0361(3) Uani 1.00 N
N5 0.05520(10) 0.2087(2) 0.73418(9) 0.0345(3) Uani 1.00 N
C6 0.02870(10) 0.3510(3) 0.64330(10) 0.0324(3) Uani 1.00 C
C7 0.14730(10) 0.0048(3) 0.61290(10) 0.0346(3) Uani 1.00 C
C8 0.12820(10) -0.0045(3) 0.72430(10) 0.0349(3) Uani 1.00 C
C9 0.0091(2) 0.2780(4) 0.82640(10) 0.0427(4) Uani 1.00 C
C10 -0.1080(2) 0.1439(7) 0.8291(2) 0.0768(8) Uani 1.00 C
C11 -0.1575(3) 0.2180(10) 0.9231(3) 0.1070(10) Uani 1.00 C
H4 0.074(2) 0.284(4) 0.506(2) 0.063(6) Uiso 1.00 H
H9A 0.068(2) 0.218(4) 0.880(2) 0.059(6) Uiso 1.00 H
H9B 0.009(2) 0.462(5) 0.833(2) 0.056(6) Uiso 1.00 H
H10A -0.162(3) 0.176(8) 0.767(3) 0.130(10) Uiso 1.00 H
H10B -0.115(3) -0.036(9) 0.825(3) 0.130(10) Uiso 1.00 H
H11A -0.101(5) 0.186(9) 1.001(4) 0.180(10) Uiso 1.00 H
H11B -0.230(4) 0.071(9) 0.925(3) 0.150(10) Uiso 1.00 H
H11C -0.181(5) 0.440(10) 0.901(5) 0.23(2) Uiso 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 1
-2 1 4
-2 0 2
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N4 C7 1_555 1_555 1_555 111.70(10) yes
C6 N4 H4 1_555 1_555 1_555 120.0(10) no
C7 N4 H4 1_555 1_555 1_555 127.0(10) no
C6 N5 C8 1_555 1_555 1_555 111.00(10) yes
C6 N5 C9 1_555 1_555 1_555 123.70(10) no
C8 N5 C9 1_555 1_555 1_555 125.40(10) no
O1 C6 N4 1_555 1_555 1_555 126.60(10) no
O1 C6 N5 1_555 1_555 1_555 125.50(10) no
N4 C6 N5 1_555 1_555 1_555 107.80(10) yes
O2 C7 N4 1_555 1_555 1_555 128.30(10) no
O2 C7 C8 1_555 1_555 1_555 127.20(10) no
N4 C7 C8 1_555 1_555 1_555 104.40(10) yes
O3 C8 N5 1_555 1_555 1_555 127.40(10) no
O3 C8 C7 1_555 1_555 1_555 127.50(10) no
N5 C8 C7 1_555 1_555 1_555 105.10(10) yes
N5 C9 C10 1_555 1_555 1_555 111.7(2) no
N5 C9 H9A 1_555 1_555 1_555 104.0(10) no
N5 C9 H9B 1_555 1_555 1_555 108.0(10) no
C10 C9 H9A 1_555 1_555 1_555 111.0(10) no
C10 C9 H9B 1_555 1_555 1_555 114.0(10) no
H9A C9 H9B 1_555 1_555 1_555 104.0(10) no
C9 C10 C11 1_555 1_555 1_555 112.2(2) no
C9 C10 H10A 1_555 1_555 1_555 111(2) no
C9 C10 H10B 1_555 1_555 1_555 120(2) no
C11 C10 H10A 1_555 1_555 1_555 112(2) no
C11 C10 H10B 1_555 1_555 1_555 104(2) no
H10A C10 H10B 1_555 1_555 1_555 94(3) no
C10 C11 H11A 1_555 1_555 1_555 119(2) no
C10 C11 H11B 1_555 1_555 1_555 104(2) no
C10 C11 H11C 1_555 1_555 1_555 97(3) no
H11A C11 H11B 1_555 1_555 1_555 101(3) no
H11A C11 H11C 1_555 1_555 1_555 115(3) no
H11B C11 H11C 1_555 1_555 1_555 119(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1_555 1_555 1.208(2) yes
O2 C7 1_555 1_555 1.200(2) yes
O3 C8 1_555 1_555 1.205(2) yes
N4 C6 1_555 1_555 1.376(2) yes
N4 C7 1_555 1_555 1.374(2) yes
N4 H4 1_555 1_555 0.92(2) no
N5 C6 1_555 1_555 1.390(2) yes
N5 C8 1_555 1_555 1.372(2) yes
N5 C9 1_555 1_555 1.459(2) yes
C7 C8 1_555 1_555 1.536(2) yes
C9 C10 1_555 1_555 1.509(3) yes
C9 H9A 1_555 1_555 0.95(2) no
C9 H9B 1_555 1_555 0.92(2) no
C10 C11 1_555 1_555 1.505(4) yes
C10 H10A 1_555 1_555 0.96(4) no
C10 H10B 1_555 1_555 0.90(4) no
C11 H11A 1_555 1_555 1.14(5) no
C11 H11B 1_555 1_555 1.11(4) no
C11 H11C 1_555 1_555 1.17(6) no
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
N4 H4 O1 3_566 0.92(2) 1.97(2) 2.881(2) 170(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
O1 C6 N4 C7 1_555 1_555 1_555 1_555 -179.70(10) no
O1 C6 N5 C8 1_555 1_555 1_555 1_555 -179.60(10) no
O1 C6 N5 C9 1_555 1_555 1_555 1_555 1.3(2) no
O2 C7 N4 C6 1_555 1_555 1_555 1_555 177.70(10) no
O2 C7 C8 O3 1_555 1_555 1_555 1_555 0.8(2) no
O2 C7 C8 N5 1_555 1_555 1_555 1_555 -177.30(10) no
O3 C8 N5 C6 1_555 1_555 1_555 1_555 -179.10(10) no
O3 C8 N5 C9 1_555 1_555 1_555 1_555 0.0(2) no
O3 C8 C7 N4 1_555 1_555 1_555 1_555 179.00(10) no
N4 C6 N5 C8 1_555 1_555 1_555 1_555 0.7(2) no
N4 C6 N5 C9 1_555 1_555 1_555 1_555 -178.30(10) no
N4 C7 C8 N5 1_555 1_555 1_555 1_555 1.00(10) no
N5 C6 N4 C7 1_555 1_555 1_555 1_555 -0.1(2) no
N5 C9 C10 C11 1_555 1_555 1_555 1_555 -178.9(3) yes
C6 N4 C7 C8 1_555 1_555 1_555 1_555 -0.60(10) no
C6 N5 C8 C7 1_555 1_555 1_555 1_555 -1.00(10) no
C6 N5 C9 C10 1_555 1_555 1_555 1_555 88.3(2) yes
C7 C8 N5 C9 1_555 1_555 1_555 1_555 178.00(10) no
C8 N5 C9 C10 1_555 1_555 1_555 1_555 -90.7(2) no
