#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/22/7052200.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_7052200
loop_
_publ_author_name
'Braga, Dario'
'Cadoni, Marcella'
'Grepioni, Fabrizia'
'Maini, Lucia'
'van de Streek, Jacco'
_publ_section_title
;
 Solid--gas reactions between 1,3-dimethylbarbituric acid and amines. A
 structural and spectroscopic study
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1935
_journal_paper_doi               10.1039/b704772j
_journal_volume                  31
_journal_year                    2007
_chemical_formula_sum            'C20 H31 N7 O9'
_chemical_formula_weight         513.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.082(2)
_cell_angle_beta                 95.887(2)
_cell_angle_gamma                95.181(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4950(10)
_cell_length_b                   12.416(2)
_cell_length_c                   12.697(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1239.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.888
_diffrn_measured_fraction_theta_max 0.888
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10652
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.742871
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0457
_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)+(0.0886P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                3883
_reflns_number_total             5575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b704772j.txt
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
H700 H 0.477(2) 0.4486(19) 0.6983(18) 0.071(6) Uiso 1 1 d . . .
H701 H 0.316(3) 0.4934(17) 0.7213(17) 0.068(6) Uiso 1 1 d . . .
C1 C 0.70612(18) 0.34620(13) 0.58279(14) 0.0461(4) Uani 1 1 d . . .
C2 C 0.8819(2) 0.25239(14) 0.44805(13) 0.0484(4) Uani 1 1 d . . .
C3 C 0.98688(18) 0.42648(13) 0.61305(14) 0.0459(4) Uani 1 1 d . . .
C4 C 0.83466(18) 0.42844(13) 0.64398(14) 0.0475(4) Uani 1 1 d . . .
H4 H 0.8183 0.4878 0.7088 0.057 Uiso 1 1 calc R . .
C5 C 0.6084(2) 0.16389(17) 0.42257(18) 0.0665(5) Uani 1 1 d . . .
H5A H 0.6014 0.1518 0.3433 0.100 Uiso 1 1 calc R . .
H5B H 0.5089 0.1840 0.4482 0.100 Uiso 1 1 calc R . .
H5C H 0.6308 0.0942 0.4346 0.100 Uiso 1 1 calc R . .
C6 C 1.1602(2) 0.33299(19) 0.47333(18) 0.0670(5) Uani 1 1 d . . .
H6A H 1.1535 0.2689 0.4034 0.100 Uiso 1 1 calc R . .
H6B H 1.2379 0.3240 0.5291 0.100 Uiso 1 1 calc R . .
H6C H 1.1915 0.4038 0.4615 0.100 Uiso 1 1 calc R . .
N1 N 0.73640(16) 0.25771(11) 0.48593(11) 0.0484(3) Uani 1 1 d . . .
N2 N 1.00456(15) 0.33653(12) 0.51284(11) 0.0476(3) Uani 1 1 d . . .
O1 O 0.56631(14) 0.34225(11) 0.60523(12) 0.0639(3) Uani 1 1 d . . .
O2 O 0.90186(17) 0.17541(12) 0.36134(11) 0.0697(4) Uani 1 1 d . . .
O3 O 1.10744(14) 0.49670(11) 0.66644(11) 0.0638(3) Uani 1 1 d . . .
C7 C 0.8818(3) -0.11895(19) 0.38363(19) 0.0755(6) Uani 1 1 d . . .
H7A H 0.7734 -0.1535 0.3755 0.113 Uiso 1 1 calc R . .
H7B H 0.8827 -0.0455 0.3740 0.113 Uiso 1 1 calc R . .
H7C H 0.9352 -0.1079 0.4577 0.113 Uiso 1 1 calc R . .
C8 C 0.8786(2) -0.28720(16) 0.21264(18) 0.0602(5) Uani 1 1 d . . .
C9 C 0.9662(2) -0.35894(19) 0.12576(18) 0.0713(5) Uani 1 1 d . . .
H9A H 0.9139 -0.3639 0.0523 0.086 Uiso 1 1 calc R . .
H9B H 0.9538 -0.4365 0.1280 0.086 Uiso 1 1 calc R . .
C10 C 1.1387(2) -0.32292(18) 0.13170(18) 0.0639(5) Uani 1 1 d . . .
C11 C 1.3788(2) -0.1880(2) 0.2294(2) 0.0834(7) Uani 1 1 d . . .
H11A H 1.4405 -0.2381 0.2544 0.125 Uiso 1 1 calc R . .
H11B H 1.4049 -0.1102 0.2826 0.125 Uiso 1 1 calc R . .
H11C H 1.4026 -0.1906 0.1563 0.125 Uiso 1 1 calc R . .
C12 C 1.1265(2) -0.15993(16) 0.30354(16) 0.0566(4) Uani 1 1 d . . .
N3 N 0.96452(17) -0.19526(12) 0.29743(13) 0.0540(4) Uani 1 1 d . . .
N4 N 1.20797(17) -0.22670(13) 0.22143(14) 0.0575(4) Uani 1 1 d . . .
O4 O 1.19296(19) -0.07375(14) 0.37825(14) 0.0822(4) Uani 1 1 d . . .
O5 O 0.73625(18) -0.30969(14) 0.20880(18) 0.0973(6) Uani 1 1 d . . .
O6 O 1.2153(2) -0.37516(17) 0.06082(16) 0.1018(6) Uani 1 1 d . . .
C13 C 1.02967(18) 0.98457(13) 0.86865(12) 0.0426(3) Uani 1 1 d . . .
C14 C 1.3090(2) 1.06321(17) 0.89544(18) 0.0655(5) Uani 1 1 d . . .
H14A H 1.4095 1.0529 0.9303 0.098 Uiso 1 1 calc R . .
H14B H 1.2774 1.1350 0.9410 0.098 Uiso 1 1 calc R . .
H14C H 1.3196 1.0645 0.8213 0.098 Uiso 1 1 calc R . .
C15 C 1.23557(18) 0.86290(14) 0.87943(14) 0.0495(4) Uani 1 1 d . . .
C16 C 1.10915(19) 0.76672(15) 0.86747(15) 0.0525(4) Uani 1 1 d . . .
H16A H 1.1234 0.7005 0.8027 0.063 Uiso 1 1 calc R . .
H16B H 1.1273 0.7454 0.9339 0.063 Uiso 1 1 calc R . .
C17 C 0.93987(19) 0.78686(14) 0.85325(14) 0.0487(4) Uani 1 1 d . . .
C18 C 0.74716(19) 0.91186(18) 0.82108(17) 0.0615(5) Uani 1 1 d . . .
H18A H 0.7335 0.9148 0.7462 0.092 Uiso 1 1 calc R . .
H18B H 0.7263 0.9836 0.8743 0.092 Uiso 1 1 calc R . .
H18C H 0.6741 0.8494 0.8237 0.092 Uiso 1 1 calc R . .
N5 N 0.91159(14) 0.89312(11) 0.85027(11) 0.0439(3) Uani 1 1 d . . .
N6 N 1.18764(14) 0.96733(11) 0.88586(11) 0.0442(3) Uani 1 1 d . . .
O7 O 0.99541(15) 1.07834(11) 0.87253(11) 0.0623(3) Uani 1 1 d . . .
O8 O 1.37542(14) 0.85107(13) 0.88652(14) 0.0788(4) Uani 1 1 d . . .
O9 O 0.83123(16) 0.71290(12) 0.84402(15) 0.0785(4) Uani 1 1 d . . .
C19 C 0.4688(2) 0.60301(17) 0.6866(2) 0.0685(5) Uani 1 1 d . . .
H19A H 0.4210 0.6710 0.7225 0.103 Uiso 1 1 calc R . .
H19B H 0.4278 0.5716 0.6073 0.103 Uiso 1 1 calc R . .
H19C H 0.5826 0.6229 0.6961 0.103 Uiso 1 1 calc R . .
C20 C 0.4854(3) 0.5579(2) 0.86125(18) 0.0739(6) Uani 1 1 d . . .
H20A H 0.6000 0.5728 0.8748 0.111 Uiso 1 1 calc R . .
H20B H 0.4498 0.5002 0.8912 0.111 Uiso 1 1 calc R . .
H20C H 0.4423 0.6280 0.8978 0.111 Uiso 1 1 calc R . .
N7 N 0.43068(17) 0.51629(12) 0.73858(13) 0.0526(3) Uani 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
_geom_angle_publ_flag
O1 C1 C4 126.73(15) . . ?
O1 C1 N1 116.70(14) . . ?
C4 C1 N1 116.57(13) . . ?
O2 C2 N1 121.45(16) . . ?
O2 C2 N2 121.69(16) . . ?
N1 C2 N2 116.86(13) . . ?
O3 C3 C4 125.69(15) . . ?
O3 C3 N2 118.06(14) . . ?
C4 C3 N2 116.25(14) . . ?
C1 C4 C3 123.08(14) . . ?
C1 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 . . ?
C2 N1 C1 123.60(14) . . ?
C2 N1 C5 117.31(14) . . ?
C1 N1 C5 119.07(14) . . ?
C2 N2 C3 123.56(13) . . ?
C2 N2 C6 117.69(14) . . ?
C3 N2 C6 118.73(15) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C8 N3 121.31(18) . . ?
O5 C8 C9 121.4(2) . . ?
N3 C8 C9 117.26(17) . . ?
C8 C9 C10 118.74(18) . . ?
C8 C9 H9A 107.6 . . ?
C10 C9 H9A 107.6 . . ?
C8 C9 H9B 107.6 . . ?
C10 C9 H9B 107.6 . . ?
H9A C9 H9B 107.1 . . ?
O6 C10 N4 121.1(2) . . ?
O6 C10 C9 121.9(2) . . ?
N4 C10 C9 116.99(16) . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N4 121.27(18) . . ?
O4 C12 N3 120.70(18) . . ?
N4 C12 N3 118.03(17) . . ?
C8 N3 C12 124.45(15) . . ?
C8 N3 C7 119.27(16) . . ?
C12 N3 C7 115.97(17) . . ?
C10 N4 C12 124.36(16) . . ?
C10 N4 C11 118.38(17) . . ?
C12 N4 C11 117.21(18) . . ?
O7 C13 N6 120.82(15) . . ?
O7 C13 N5 120.69(14) . . ?
N6 C13 N5 118.46(13) . . ?
N6 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 C15 N6 120.98(16) . . ?
O8 C15 C16 121.63(16) . . ?
N6 C15 C16 117.35(13) . . ?
C17 C16 C15 118.06(14) . . ?
C17 C16 H16A 107.8 . . ?
C15 C16 H16A 107.8 . . ?
C17 C16 H16B 107.8 . . ?
C15 C16 H16B 107.8 . . ?
H16A C16 H16B 107.1 . . ?
O9 C17 N5 121.22(15) . . ?
O9 C17 C16 121.56(16) . . ?
N5 C17 C16 117.22(14) . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N5 C13 124.31(13) . . ?
C17 N5 C18 119.20(14) . . ?
C13 N5 C18 116.43(14) . . ?
C15 N6 C13 124.06(13) . . ?
C15 N6 C14 118.69(14) . . ?
C13 N6 C14 116.66(14) . . ?
N7 C19 H19A 109.5 . . ?
N7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 N7 C19 113.39(16) . . ?
C20 N7 H700 112.0(12) . . ?
C19 N7 H700 106.9(12) . . ?
C20 N7 H701 111.6(12) . . ?
C19 N7 H701 107.0(12) . . ?
H700 N7 H701 105.4(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2500(19) . ?
C1 C4 1.385(2) . ?
C1 N1 1.405(2) . ?
C2 O2 1.2246(19) . ?
C2 N1 1.370(2) . ?
C2 N2 1.375(2) . ?
C3 O3 1.249(2) . ?
C3 C4 1.389(2) . ?
C3 N2 1.408(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.461(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N2 1.460(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N3 1.468(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O5 1.208(2) . ?
C8 N3 1.356(3) . ?
C8 C9 1.476(3) . ?
C9 C10 1.479(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O6 1.204(2) . ?
C10 N4 1.368(3) . ?
C11 N4 1.469(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.203(2) . ?
C12 N4 1.383(2) . ?
C12 N3 1.392(2) . ?
C13 O7 1.2113(19) . ?
C13 N6 1.3850(19) . ?
C13 N5 1.384(2) . ?
C14 N6 1.466(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O8 1.2082(19) . ?
C15 N6 1.372(2) . ?
C15 C16 1.487(2) . ?
C16 C17 1.485(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O9 1.208(2) . ?
C17 N5 1.375(2) . ?
C18 N5 1.468(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N7 1.473(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N7 1.471(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N7 H700 0.96(2) . ?
N7 H701 0.97(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175818
