#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206120.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_2206120
loop_
_publ_author_name
'Rodriguez, Mark A.'
'Andrews, Nicholas L.'
'Boyle, Timothy J.'
'Frazer, Colleen S.'
_publ_section_title
;
 N-Methylimidazolidinetrione
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2288
_journal_page_last               o2290
_journal_paper_doi               10.1107/S1600536805019690
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C4 H4 N2 O3'
_chemical_formula_moiety         'C4 H4 N2 O3'
_chemical_formula_sum            'C4 H4 N2 O3'
_chemical_formula_weight         128.09
_chemical_name_systematic
;
N-Methylimidazolidinetrione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8966(8)
_cell_length_b                   7.2049(12)
_cell_length_c                   14.719(2)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.77
_cell_volume                     519.28(14)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'XSHELL (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 1998)'
_diffrn_ambient_temperature      168(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4577
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0313
_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)+(0.0435P)²+0.0879P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                632
_reflns_number_total             731
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bd6004.cif
_cod_data_source_block           I
_cod_original_cell_volume        519.27(15)
_cod_database_code               2206120
_cod_database_fobs_code          2206120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.4710(4) 0.3568(3) 0.41926(13) 0.0231(4) Uani d . 1 C
C2 0.4846(5) 0.1652(3) 0.37199(13) 0.0241(4) Uani d . 1 C
C3 0.8358(4) 0.3486(3) 0.32407(13) 0.0221(4) Uani d . 1 C
C4 0.7525(5) 0.6460(3) 0.40907(15) 0.0306(5) Uani d . 1 C
H4A 0.5987 0.7277 0.3943 0.046 Uiso calc R 1 H
H4B 0.9149 0.6865 0.3756 0.046 Uiso calc R 1 H
H4C 0.7891 0.6518 0.4745 0.046 Uiso calc R 1 H
N1 0.6851(4) 0.4555(2) 0.38358(11) 0.0231(4) Uani d . 1 N
N2 0.7086(4) 0.1781(2) 0.31660(12) 0.0248(4) Uani d . 1 N
H2 0.783(6) 0.088(4) 0.2892(17) 0.042(8) Uiso d . 1 H
O1 0.3048(3) 0.4072(2) 0.47416(10) 0.0304(4) Uani d . 1 O
O2 0.3306(3) 0.0368(2) 0.38108(10) 0.0321(4) Uani d . 1 O
O3 1.0429(3) 0.3944(2) 0.28512(10) 0.0271(4) Uani d . 1 O
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0193(9) 0.0278(10) 0.0223(9) 0.0047(9) -0.0008(9) 0.0028(8)
C2 0.0207(10) 0.0271(10) 0.0246(10) 0.0018(9) -0.0042(9) 0.0027(9)
C3 0.0215(10) 0.0243(10) 0.0203(9) 0.0035(9) -0.0034(9) 0.0041(8)
C4 0.0372(12) 0.0214(10) 0.0332(11) 0.0014(10) 0.0008(10) -0.0028(9)
N1 0.0235(9) 0.0214(8) 0.0245(8) 0.0013(7) 0.0018(8) -0.0009(7)
N2 0.0232(9) 0.0224(9) 0.0287(9) 0.0012(8) 0.0024(8) -0.0027(8)
O1 0.0254(8) 0.0375(8) 0.0282(7) 0.0052(8) 0.0032(7) -0.0007(7)
O2 0.0254(8) 0.0301(8) 0.0408(9) -0.0047(7) -0.0027(8) 0.0059(7)
O3 0.0253(8) 0.0297(8) 0.0264(7) 0.0010(7) 0.0056(7) 0.0052(7)
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
O1 C1 N1 128.1(2) y
O1 C1 C2 126.9(2) y
N1 C1 C2 104.92(17) y
O2 C2 N2 128.4(2) y
O2 C2 C1 127.6(2) y
N2 C2 C1 103.98(18) y
O3 C3 N1 126.6(2) y
O3 C3 N2 125.6(2) y
N1 C3 N2 107.79(18) y
N1 C4 H4A 109.5 y
N1 C4 H4B 109.5 y
H4A C4 H4B 109.5 y
N1 C4 H4C 109.5 y
H4A C4 H4C 109.5 y
H4B C4 H4C 109.5 y
C1 N1 C3 111.25(17) y
C1 N1 C4 124.16(18) y
C3 N1 C4 124.52(18) y
C2 N2 C3 111.97(18) y
C2 N2 H2 125.2(18) y
C3 N2 H2 121.7(18) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.204(2) yes
C1 N1 1.372(3) yes
C1 C2 1.545(3) yes
C2 O2 1.202(3) yes
C2 N2 1.369(3) yes
C3 O3 1.210(2) yes
C3 N2 1.381(3) yes
C3 N1 1.382(3) yes
C4 N1 1.460(3) yes
C4 H4A 0.9800 yes
C4 H4B 0.9800 yes
C4 H4C 0.9800 yes
N2 H2 0.86(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 109811
