#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018391.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_2018391
loop_
_publ_author_name
'Gelbrich, Thomas'
'Rossi, Denise'
'Griesser, Ulrich J.'
_publ_section_title
;
 Two polymorphs and the diethylammonium salt of the barbiturate eldoral
;
_journal_coeditor_code           SK3420
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o65
_journal_page_last               o70
_journal_paper_doi               10.1107/S0108270111055120
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H17 N3 O3'
_chemical_formula_moiety         'C11 H17 N3 O3'
_chemical_formula_sum            'C11 H17 N3 O3'
_chemical_formula_weight         239.28
_chemical_name_common            eldoral
_chemical_name_systematic
;
5-ethyl-5-(piperidin-1-yl)-1,3-diazinane-2,4,6-trione
;
_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'
_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                 98.189(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8761(2)
_cell_length_b                   12.7102(4)
_cell_length_c                   11.9438(3)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.1820
_cell_measurement_theta_min      3.4714
_cell_volume                     1183.46(6)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2003)'
_computing_molecular_graphics
;
XP in SHELXTL (Bruker, 1998) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini Ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6405
_diffrn_reflns_theta_full        67.29
_diffrn_reflns_theta_max         67.29
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7346
_exptl_absorpt_correction_T_min  0.7189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0442
_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)+(0.0823P)²+0.3019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1900
_reflns_number_total             2111
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3420.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018391
_cod_database_fobs_code          2018391
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_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_symmetry_multiplicity
O O2 0.36517(13) 0.45037(8) 0.58288(8) 0.0228(3) Uani d . 1 1
O O4 0.44593(13) 0.31051(8) 0.24714(8) 0.0236(3) Uani d . 1 1
O O6 0.16698(14) 0.12057(8) 0.51336(8) 0.0243(3) Uani d . 1 1
N N1 0.25601(15) 0.28807(10) 0.54236(9) 0.0186(3) Uani d D 1 1
H H1 0.226(2) 0.2883(15) 0.6090(13) 0.029(5) Uiso d D 1 1
N N3 0.41092(15) 0.37557(10) 0.41746(10) 0.0189(3) Uani d D 1 1
H H3 0.472(3) 0.4313(14) 0.4043(17) 0.040(5) Uiso d D 1 1
N N9 0.14381(15) 0.18896(9) 0.26946(9) 0.0178(3) Uani d . 1 1
C C2 0.34506(17) 0.37528(11) 0.51811(11) 0.0182(3) Uani d . 1 1
C C4 0.38837(17) 0.29899(11) 0.33517(11) 0.0178(3) Uani d . 1 1
C C5 0.29329(17) 0.19810(11) 0.36097(11) 0.0175(3) Uani d . 1 1
C C6 0.23423(18) 0.19751(11) 0.47846(11) 0.0188(3) Uani d . 1 1
C C7 0.42276(18) 0.10750(12) 0.35950(12) 0.0208(3) Uani d . 1 1
H H7A 0.3682 0.0409 0.3785 0.026(4) Uiso calc R 1 1
H H7B 0.4530 0.1004 0.2822 0.022(4) Uiso calc R 1 1
C C8 0.58668(19) 0.12463(13) 0.44271(13) 0.0260(4) Uani d . 1 1
H H8A 0.6449 0.1883 0.4216 0.035(5) Uiso calc R 1 1
H H8B 0.6627 0.0639 0.4405 0.035(5) Uiso calc R 1 1
H H8C 0.5575 0.1327 0.5193 0.033(5) Uiso calc R 1 1
C C10 0.06325(19) 0.08342(12) 0.25699(12) 0.0231(4) Uani d . 1 1
H H10A 0.0107 0.0665 0.3253 0.025(4) Uiso calc R 1 1
H H10B 0.1517 0.0297 0.2490 0.029(5) Uiso calc R 1 1
C C11 -0.0739(2) 0.08171(13) 0.15296(13) 0.0283(4) Uani d . 1 1
H H11A -0.0192 0.0937 0.0844 0.025(4) Uiso calc R 1 1
H H11B -0.1289 0.0115 0.1462 0.034(5) Uiso calc R 1 1
C C12 -0.2103(2) 0.16542(14) 0.15971(14) 0.0298(4) Uani d . 1 1
H H12A -0.2906 0.1668 0.0880 0.035(5) Uiso calc R 1 1
H H12B -0.2766 0.1481 0.2217 0.037(5) Uiso calc R 1 1
C C13 -0.12730(19) 0.27285(13) 0.18097(13) 0.0267(4) Uani d . 1 1
H H13A -0.2155 0.3249 0.1946 0.035(5) Uiso calc R 1 1
H H13B -0.0778 0.2953 0.1131 0.026(4) Uiso calc R 1 1
C C14 0.01334(18) 0.26990(12) 0.28261(12) 0.0234(4) Uani d . 1 1
H H14A 0.0694 0.3397 0.2920 0.027(4) Uiso calc R 1 1
H H14B -0.0385 0.2549 0.3517 0.028(4) Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C6 126.01(12)
C2 N1 H1 114.2(13)
C6 N1 H1 119.0(13)
C2 N3 C4 126.56(12)
C2 N3 H3 116.1(13)
C4 N3 H3 117.3(13)
C14 N9 C10 110.27(11)
C14 N9 C5 110.84(10)
C10 N9 C5 115.19(11)
O2 C2 N1 121.54(12)
O2 C2 N3 121.27(13)
N1 C2 N3 117.19(12)
N9 C5 C4 105.90(10)
N9 C5 C7 112.83(11)
C4 C5 C7 106.21(11)
N9 C5 C6 110.96(10)
C4 C5 C6 113.92(11)
C7 C5 C6 107.05(11)
O4 C4 N3 120.52(13)
O4 C4 C5 121.84(12)
N3 C4 C5 117.61(12)
O6 C6 N1 120.57(12)
O6 C6 C5 121.34(12)
N1 C6 C5 118.08(12)
C8 C7 C5 112.67(12)
C8 C7 H7A 109.1
C5 C7 H7A 109.1
C8 C7 H7B 109.1
C5 C7 H7B 109.1
H7A C7 H7B 107.8
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N9 C10 C11 109.75(12)
N9 C10 H10A 109.7
C11 C10 H10A 109.7
N9 C10 H10B 109.7
C11 C10 H10B 109.7
H10A C10 H10B 108.2
C12 C11 C10 111.71(13)
C12 C11 H11A 109.3
C10 C11 H11A 109.3
C12 C11 H11B 109.3
C10 C11 H11B 109.3
H11A C11 H11B 107.9
C13 C12 C11 110.29(12)
C13 C12 H12A 109.6
C11 C12 H12A 109.6
C13 C12 H12B 109.6
C11 C12 H12B 109.6
H12A C12 H12B 108.1
C12 C13 C14 110.97(13)
C12 C13 H13A 109.4
C14 C13 H13A 109.4
C12 C13 H13B 109.4
C14 C13 H13B 109.4
H13A C13 H13B 108.0
N9 C14 C13 111.72(12)
N9 C14 H14A 109.3
C13 C14 H14A 109.3
N9 C14 H14B 109.3
C13 C14 H14B 109.3
H14A C14 H14B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C2 1.2246(17)
O4 C4 1.2117(17)
O6 C6 1.2139(18)
N1 C2 1.3647(18)
N1 C6 1.3782(19)
N1 H1 0.862(14)
N3 C2 1.3755(18)
N3 C4 1.3767(18)
N3 H3 0.881(16)
N9 C14 1.4782(18)
N9 C10 1.4824(18)
N9 C5 1.4926(17)
C5 C4 1.5381(19)
C5 C7 1.5399(19)
C5 C6 1.5400(18)
C7 C8 1.529(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 C11 1.526(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.522(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.520(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.523(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
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
N1 H1 N9 4_566 0.862(14) 2.128(15) 2.9843(16) 172.1(17)
N3 H3 O2 3_666 0.881(16) 1.970(16) 2.8295(16) 164.6(19)
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
C2 C5 C7 C8 -4.38(16)
C8 C7 C5 N9 172.30(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 91912
2 PubChem 101726
