#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/14/2011432.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_2011432
loop_
_publ_author_name
'Spirlet, Marie-Rose'
'Desreux, Jean F.'
'Riondel, Alain'
'Herbst, Gilles'
'Goudiakas, Jean'
_publ_section_title
;
 2-(2-Oxoimidazolidinyl)ethyl 2-methylprop-2-enoate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1258
_journal_page_last               1259
_journal_paper_doi               10.1107/S0108270100009835
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C9 H14 N2 O3'
_chemical_formula_moiety         'C9 H14 N2 O3'
_chemical_formula_sum            'C9 H14 N2 O3'
_chemical_formula_weight         198.22
_chemical_name_systematic
;
2-(2-oxoimidazolidinyl)ethyl 2-methylprop-2-enoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.197(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6304(8)
_cell_length_b                   11.3329(10)
_cell_length_c                   7.0306(6)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     998.42(14)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .989
_diffrn_measured_fraction_theta_max .989
_diffrn_measurement_device_type  'Siemens R3m/V 4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .020
_diffrn_reflns_av_sigmaI/netI    .040
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1866
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .100
_exptl_absorpt_correction_T_max  .980
_exptl_absorpt_correction_T_min  .933
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         .16
_refine_diff_density_min         -.12
_refine_ls_extinction_coef       .024(8)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .950
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .950
_refine_ls_R_factor_all          .045
_refine_ls_R_factor_gt           .032
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0521P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .090
_reflns_number_gt                1287
_reflns_number_total             1739
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1113.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011432
_cod_database_fobs_code          2011432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .37741(10) .01561(10) .31547(18) .0479(4) Uani d . 1 . . N
C2 .40906(11) -.09828(12) .3120(2) .0425(4) Uani d . 1 . . C
O2 .45777(9) -.14318(9) .18905(16) .0588(3) Uani d . 1 . . O
N3 .37725(12) -.15247(13) .4640(2) .0635(4) Uani d . 1 . . N
H3 .4044(14) -.2177(18) .505(3) .069(6) Uiso d . 1 . . H
C4 .33111(16) -.07326(15) .5895(3) .0585(5) Uani d . 1 . . C
H4 .2625(16) -.0998(16) .620(2) .070(5) Uiso d . 1 . . H
H4' .3752(16) -.0636(19) .714(3) .095(7) Uiso d . 1 . . H
C5 .32236(15) .04172(14) .4776(2) .0537(4) Uani d . 1 . . C
H5 .2518(17) .0634(17) .440(3) .077(6) Uiso d . 1 . . H
H5' .3614(14) .1111(17) .559(2) .072(5) Uiso d . 1 . . H
C6 .38685(13) .09691(14) .1601(2) .0514(4) Uani d . 1 . . C
H6 .4253(13) .1710(16) .216(3) .070(5) Uiso d . 1 . . H
H6' .4270(12) .0529(14) .070(2) .053(4) Uiso d . 1 . . H
C7 .28199(14) .13312(14) .0510(3) .0560(4) Uani d . 1 . . C
H7 .2940(14) .1761(17) -.068(3) .075(5) Uiso d . 1 . . H
H7' .2357(14) .1804(16) .123(2) .063(5) Uiso d . 1 . . H
O8 .22224(8) .02686(9) -.00198(16) .0550(3) Uani d . 1 . . O
O9 .11230(10) .12760(11) -.21436(19) .0756(4) Uani d . 1 . . O
C9 .13597(12) .03736(13) -.1317(2) .0485(4) Uani d . 1 . . C
C10 .07659(12) -.07629(14) -.1588(2) .0500(4) Uani d . 1 . . C
C11 -.01372(16) -.07624(19) -.2786(3) .0686(5) Uani d . 1 . . C
H11 -.0539(16) -.1449(19) -.303(3) .086(6) Uiso d . 1 . . H
H11' -.0353(16) -.001(2) -.343(3) .090(7) Uiso d . 1 . . H
C12 .11847(19) -.18016(17) -.0493(3) .0681(5) Uani d . 1 . . C
H12 .0709(14) -.2483(19) -.076(3) .078(6) Uiso d . 1 . . H
H12' .1158(19) -.164(2) .100(4) .131(9) Uiso d . 1 . . H
H12'' .1830(17) -.197(2) -.070(3) .088(7) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . 112.60(12) yes
C2 N1 C6 . 122.83(13) yes
C5 N1 C6 . 124.16(12) yes
O2 C2 N3 . 126.69(14) yes
O2 C2 N1 . 125.58(14) yes
N3 C2 N1 . 107.73(13) yes
C2 O2 N3 4 122.55(9) ?
C2 N3 C4 . 113.00(14) yes
C4 N3 O2 . 138.32(12) ?
C2 N3 H3 . 121.4(12) ?
C4 N3 H3 . 120.9(12) ?
N3 C4 C5 . 103.11(13) yes
N3 C4 H4 . 112.9(11) ?
C5 C4 H4 . 111.9(11) ?
N3 C4 H4' . 112.9(12) ?
C5 C4 H4' . 111.2(13) ?
H4 C4 H4' . 105.0(15) ?
N1 C5 C4 . 102.89(12) yes
N1 C5 H5 . 111.6(12) ?
C4 C5 H5 . 112.4(12) ?
N1 C5 H5' . 110.1(9) ?
C4 C5 H5' . 110.9(10) ?
H5 C5 H5' . 108.9(15) ?
N1 C6 C7 . 114.15(14) yes
N1 C6 H6 . 108.1(10) ?
C7 C6 H6 . 108.6(10) ?
N1 C6 H6' . 105.0(9) ?
C7 C6 H6' . 107.4(9) ?
H6 C6 H6' . 113.7(13) ?
O8 C7 C6 . 107.61(12) yes
O8 C7 H7 . 108.6(11) ?
C6 C7 H7 . 110.2(10) ?
O8 C7 H7' . 105.2(10) ?
C6 C7 H7' . 115.4(10) ?
H7 C7 H7' . 109.4(15) ?
C9 O8 C7 . 117.19(12) yes
O9 C9 O8 . 122.76(15) yes
O9 C9 C10 . 125.86(15) yes
O8 C9 C10 . 111.38(13) yes
C11 C10 C12 . 123.79(17) yes
C11 C10 C9 . 117.28(16) yes
C12 C10 C9 . 118.91(15) yes
C10 C11 H11 . 121.3(13) ?
C10 C11 H11' . 117.2(12) ?
H11 C11 H11' . 121.5(18) ?
C10 C12 H12 . 111.1(11) ?
C10 C12 H12' . 109.0(14) ?
H12 C12 H12' . 103.0(17) ?
C10 C12 H12'' . 111.7(15) ?
H12 C12 H12" . 111.5(18) ?
H12' C12 H12" . 110(2) ?
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
N1 C2 . 1.3523(18) yes
N1 C5 . 1.438(2) yes
N1 C6 . 1.4451(19) yes
C2 O2 . 1.2318(16) yes
C2 N3 . 1.3374(19) yes
O2 N3 4 2.9151(18) yes
N3 C4 . 1.433(2) yes
N3 H3 . .85(2) yes
C4 C5 . 1.519(2) yes
C4 H4 . .968(19) ?
C4 H4' . .98(2) ?
C5 H5 . .93(2) ?
C5 H5' . 1.058(19) ?
C6 C7 . 1.502(2) yes
C6 H6 . 1.024(18) ?
C6 H6' . .994(16) ?
C7 O8 . 1.4450(19) yes
C7 H7 . .998(19) ?
C7 H7' . .981(18) ?
O8 C9 . 1.3357(18) yes
O9 C9 . 1.1956(18) yes
C9 C10 . 1.491(2) yes
C10 C11 . 1.330(3) yes
C10 C12 . 1.468(3) yes
C11 H11 . .93(2) ?
C11 H11' . .99(2) ?
C12 H12 . .98(2) ?
C12 H12' . 1.07(3) ?
C12 H12'' . .87(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
_geom_torsion_publ_flag
N1 C6 C7 O8 -50.8(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 643493
