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#$Date: 2023-04-20 11:25:31 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107097.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107097
loop_
_publ_author_name
'Barakat, Assem'
'Ghabbour, Hazem A.'
'Al-Majid, Abdullah Mohammed'
'Islam, Mohammad Shahidul'
'Shaik, Mohammed Rafi'
_publ_section_title
;
 Crystal structure of diethylammonium
 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C10H19N3O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1063
_journal_page_last               1064
_journal_paper_doi               10.1515/ncrs-2016-0051
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C10 H19 N3 O3'
_chemical_formula_weight         229.28
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4714(2)
_cell_length_b                   17.8690(7)
_cell_length_c                   14.6323(6)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.04
_cell_measurement_theta_min      2.28
_cell_volume                     1164.17(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25648
_diffrn_reflns_theta_full        33.17
_diffrn_reflns_theta_max         33.17
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0518
_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)+(0.0731P)²+0.5388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                3160
_reflns_number_total             4436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0051_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8107097
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_label
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5693(2) 0.63954(5) 0.55115(6) 0.01686(18) Uani 1 1 d . . .
O2 O 1.01732(19) 0.65228(5) 0.85558(6) 0.01701(19) Uani 1 1 d . . .
O3 O 0.3361(2) 0.47036(5) 0.76703(6) 0.0207(2) Uani 1 1 d . . .
N1 N 0.6862(2) 0.55934(5) 0.80938(6) 0.01324(19) Uani 1 1 d . . .
N2 N 0.4494(2) 0.55573(5) 0.65952(6) 0.01191(18) Uani 1 1 d . . .
N3 N 0.2275(2) 0.74202(6) 0.45099(7) 0.01223(19) Uani 1 1 d . . .
C1 C 0.6092(2) 0.61877(6) 0.63375(8) 0.0120(2) Uani 1 1 d . . .
C2 C 0.8023(3) 0.65257(6) 0.70195(8) 0.0137(2) Uani 1 1 d . . .
H2A H 0.9080 0.6964 0.6872 0.016 Uiso 1 1 calc R . .
C3 C 0.8456(2) 0.62417(6) 0.79107(8) 0.0121(2) Uani 1 1 d . . .
C4 C 0.7332(4) 0.52439(8) 0.89953(9) 0.0250(3) Uani 1 1 d . . .
H4A H 0.7562 0.4702 0.8923 0.038 Uiso 1 1 calc R . .
H4B H 0.5599 0.5345 0.9341 0.038 Uiso 1 1 calc R . .
H4C H 0.9149 0.5450 0.9328 0.038 Uiso 1 1 calc R . .
C5 C 0.4807(2) 0.52529(6) 0.74650(8) 0.0130(2) Uani 1 1 d . . .
C6 C 0.2295(3) 0.52080(7) 0.59247(9) 0.0170(2) Uani 1 1 d . . .
H6A H 0.0643 0.5001 0.6241 0.025 Uiso 1 1 calc R . .
H6B H 0.3264 0.4805 0.5606 0.025 Uiso 1 1 calc R . .
H6C H 0.1506 0.5584 0.5478 0.025 Uiso 1 1 calc R . .
C7 C 0.2712(3) 0.82170(7) 0.58976(9) 0.0209(3) Uani 1 1 d . . .
H7A H 0.1579 0.8534 0.6290 0.031 Uiso 1 1 calc R . .
H7B H 0.4233 0.8519 0.5627 0.031 Uiso 1 1 calc R . .
H7C H 0.3699 0.7814 0.6266 0.031 Uiso 1 1 calc R . .
C8 C 0.0587(3) 0.78828(7) 0.51393(8) 0.0159(2) Uani 1 1 d . . .
H8A H -0.0921 0.7567 0.5411 0.019 Uiso 1 1 calc R . .
H8B H -0.0490 0.8289 0.4787 0.019 Uiso 1 1 calc R . .
C9 C 0.0283(3) 0.69953(7) 0.38160(8) 0.0158(2) Uani 1 1 d . . .
H9A H -0.0979 0.7351 0.3431 0.019 Uiso 1 1 calc R . .
H9B H -0.1066 0.6665 0.4134 0.019 Uiso 1 1 calc R . .
C10 C 0.2127(3) 0.65281(7) 0.32121(9) 0.0188(2) Uani 1 1 d . . .
H10A H 0.0782 0.6232 0.2787 0.028 Uiso 1 1 calc R . .
H10B H 0.3439 0.6192 0.3596 0.028 Uiso 1 1 calc R . .
H10C H 0.3353 0.6858 0.2863 0.028 Uiso 1 1 calc R . .
H2N3 H 0.345(3) 0.7742(9) 0.4209(10) 0.016(4) Uiso 1 1 d . . .
H1N3 H 0.347(4) 0.7072(10) 0.4851(12) 0.030(5) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N1 C3 123.85(10) . .
C5 N1 C4 116.50(10) . .
C3 N1 C4 119.65(10) . .
C5 N2 C1 123.59(9) . .
C5 N2 C6 117.09(9) . .
C1 N2 C6 119.30(9) . .
C8 N3 C9 113.37(9) . .
C8 N3 H2N3 107.1(9) . .
C9 N3 H2N3 108.9(9) . .
C8 N3 H1N3 109.6(11) . .
C9 N3 H1N3 107.5(11) . .
H2N3 N3 H1N3 110.4(14) . .
O1 C1 C2 125.56(10) . .
O1 C1 N2 117.56(10) . .
C2 C1 N2 116.87(10) . .
C1 C2 C3 122.28(10) . .
C1 C2 H2A 118.9 . .
C3 C2 H2A 118.9 . .
O2 C3 C2 125.11(11) . .
O2 C3 N1 118.10(10) . .
C2 C3 N1 116.78(10) . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O3 C5 N2 122.00(11) . .
O3 C5 N1 121.50(10) . .
N2 C5 N1 116.49(10) . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N3 C8 C7 110.56(9) . .
N3 C8 H8A 109.5 . .
C7 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N3 C9 C10 110.73(9) . .
N3 C9 H9A 109.5 . .
C10 C9 H9A 109.5 . .
N3 C9 H9B 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2612(14) .
O2 C3 1.2647(14) .
O3 C5 1.2277(14) .
N1 C5 1.3804(15) .
N1 C3 1.3989(15) .
N1 C4 1.4572(16) .
N2 C5 1.3793(15) .
N2 C1 1.4040(14) .
N2 C6 1.4634(14) .
N3 C8 1.4930(15) .
N3 C9 1.4948(15) .
N3 H2N3 0.919(16) .
N3 H1N3 0.934(19) .
C1 C2 1.3957(16) .
C2 C3 1.3962(16) .
C2 H2A 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.5156(18) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5138(17) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N2 C1 O1 177.35(10) . . . .
C6 N2 C1 O1 -4.63(15) . . . .
C5 N2 C1 C2 -1.86(16) . . . .
C6 N2 C1 C2 176.17(10) . . . .
O1 C1 C2 C3 -176.84(11) . . . .
N2 C1 C2 C3 2.30(16) . . . .
C1 C2 C3 O2 179.98(11) . . . .
C1 C2 C3 N1 0.27(16) . . . .
C5 N1 C3 O2 176.64(10) . . . .
C4 N1 C3 O2 -3.05(16) . . . .
C5 N1 C3 C2 -3.63(16) . . . .
C4 N1 C3 C2 176.68(11) . . . .
C1 N2 C5 O3 179.53(11) . . . .
C6 N2 C5 O3 1.46(16) . . . .
C1 N2 C5 N1 -1.17(16) . . . .
C6 N2 C5 N1 -179.24(9) . . . .
C3 N1 C5 O3 -176.65(10) . . . .
C4 N1 C5 O3 3.04(17) . . . .
C3 N1 C5 N2 4.05(16) . . . .
C4 N1 C5 N2 -176.26(10) . . . .
C9 N3 C8 C7 172.67(10) . . . .
C8 N3 C9 C10 -178.97(10) . . . .
