#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/83/4508383.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_4508383
loop_
_publ_author_name
'Ivanova, Bojidarka'
'Spiteller, Michael'
_publ_section_title
;
 On the application of the organic barbiturates as NLO materials
;
_journal_name_full               'Crystal Growth and Design'
_journal_page_first              2470
_journal_page_last               2474
_journal_paper_doi               10.1021/cg100284r
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         C6H6N2O,C4H3N3O4
_chemical_formula_sum            'C10 H9 N5 O5'
_chemical_formula_weight         279.22
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.971(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.142(4)
_cell_length_b                   5.7613(17)
_cell_length_c                   15.534(5)
_cell_measurement_temperature    300(2)
_cell_volume                     1169.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6984
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.266
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0547
_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)+(0.0691P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                1451
_reflns_number_total             2067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Struct-9.cif
_cod_data_source_block           bi9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4508383
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_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
O1 O 0.82604(15) 0.6469(4) 0.24950(13) 0.0497(6) Uani 1 1 d .
H1 H 0.8216 0.5233 0.2232 0.075 Uiso 1 1 calc R
O2 O 0.28307(16) 0.8057(4) 0.34582(14) 0.0542(6) Uani 1 1 d .
H2 H 0.3422 0.8518 0.3470 0.081 Uiso 1 1 calc R
O3 O -0.07631(14) 0.1929(3) 0.43237(13) 0.0487(6) Uani 1 1 d .
O4 O 0.26509(15) 0.2591(4) 0.50135(14) 0.0532(6) Uani 1 1 d .
O5 O 0.08035(16) 0.7726(4) 0.30402(16) 0.0720(8) Uani 1 1 d .
N1 N 0.72841(17) 0.7136(4) 0.27069(15) 0.0389(6) Uani 1 1 d .
N2 N 0.46444(16) 0.9792(4) 0.36297(14) 0.0364(6) Uani 1 1 d .
N3 N 0.09535(16) 0.2264(4) 0.46327(14) 0.0360(6) Uani 1 1 d .
H3 H 0.0951 0.1051 0.4955 0.043 Uiso 1 1 calc R
N4 N 0.00528(17) 0.4841(4) 0.37037(14) 0.0374(6) Uani 1 1 d .
H4 H -0.0526 0.5300 0.3452 0.045 Uiso 1 1 calc R
C1 C 0.7319(2) 0.9061(4) 0.30830(16) 0.0339(6) Uani 1 1 d .
H1A H 0.7937 0.9857 0.3166 0.041 Uiso 1 1 calc R
C2 C 0.64083(18) 1.0080(4) 0.33924(15) 0.0287(6) Uani 1 1 d .
C3 C 0.5469(2) 0.8932(5) 0.33120(16) 0.0333(6) Uani 1 1 d .
H3A H 0.5416 0.7513 0.3026 0.040 Uiso 1 1 calc R
C4 C 0.4703(2) 1.1841(5) 0.40375(17) 0.0387(7) Uani 1 1 d .
H4A H 0.4125 1.2434 0.4258 0.046 Uiso 1 1 calc R
C5 C 0.5601(2) 1.3092(5) 0.41378(18) 0.0407(7) Uani 1 1 d .
H5 H 0.5628 1.4522 0.4417 0.049 Uiso 1 1 calc R
C6 C 0.6459(2) 1.2197(4) 0.38195(17) 0.0355(7) Uani 1 1 d .
H6 H 0.7073 1.3013 0.3891 0.043 Uiso 1 1 calc R
N5 N 0.2796(2) 0.6294(4) 0.39758(14) 0.0429(6) Uani 1 1 d .
C8 C 0.1876(2) 0.5357(4) 0.40068(16) 0.0318(6) Uani 1 1 d .
C9 C 0.1892(2) 0.3326(5) 0.45883(16) 0.0345(7) Uani 1 1 d .
C10 C 0.0033(2) 0.2935(5) 0.42204(16) 0.0345(7) Uani 1 1 d .
C11 C 0.0902(2) 0.6120(5) 0.35387(17) 0.0386(7) 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
N1 O1 H1 109.5
N5 O2 H2 109.5
C1 N1 O1 111.1(2)
C3 N2 C4 119.6(2)
C10 N3 C9 127.0(2)
C10 N3 H3 116.5
C9 N3 H3 116.5
C10 N4 C11 127.1(2)
C10 N4 H4 116.4
C11 N4 H4 116.4
N1 C1 C2 121.2(2)
N1 C1 H1A 119.4
C2 C1 H1A 119.4
C6 C2 C3 117.3(2)
C6 C2 C1 120.7(2)
C3 C2 C1 121.9(2)
N2 C3 C2 122.5(2)
N2 C3 H3A 118.8
C2 C3 H3A 118.8
N2 C4 C5 121.5(2)
N2 C4 H4A 119.3
C5 C4 H4A 119.3
C6 C5 C4 119.1(3)
C6 C5 H5 120.4
C4 C5 H5 120.4
C5 C6 C2 120.0(2)
C5 C6 H6 120.0
C2 C6 H6 120.0
O2 N5 C8 115.5(2)
N5 C8 C11 127.5(2)
N5 C8 C9 112.9(2)
C11 C8 C9 119.7(2)
O4 C9 N3 120.3(2)
O4 C9 C8 124.6(2)
N3 C9 C8 115.1(2)
O3 C10 N4 121.9(2)
O3 C10 N3 122.3(2)
N4 C10 N3 115.8(2)
O5 C11 N4 119.6(2)
O5 C11 C8 125.2(2)
N4 C11 C8 115.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.411(3)
O1 H1 0.8200
O2 N5 1.299(3)
O2 H2 0.8200
O3 C10 1.221(3)
O4 C9 1.214(3)
O5 C11 1.205(3)
N1 C1 1.253(3)
N2 C3 1.332(3)
N2 C4 1.338(3)
N3 C10 1.364(3)
N3 C9 1.384(3)
N3 H3 0.8600
N4 C10 1.362(3)
N4 C11 1.383(3)
N4 H4 0.8600
C1 C2 1.459(3)
C1 H1A 0.9300
C2 C6 1.387(3)
C2 C3 1.395(3)
C3 H3A 0.9300
C4 C5 1.378(4)
C4 H4A 0.9300
C5 C6 1.377(4)
C5 H5 0.9300
C6 H6 0.9300
N5 C8 1.331(3)
C8 C11 1.472(4)
C8 C9 1.477(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146683
