#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:13:03 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179619 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/83/4508391.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_4508391
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         'C4 H3 N3 O4, C2 H4 N4, O'
_chemical_formula_sum            'C6 H7 N7 O5'
_chemical_formula_weight         257.19
_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                82.580(9)
_cell_angle_beta                 71.724(9)
_cell_angle_gamma                66.004(9)
_cell_formula_units_Z            2
_cell_length_a                   6.8634(19)
_cell_length_b                   8.126(2)
_cell_length_c                   10.584(3)
_cell_measurement_temperature    199(2)
_cell_volume                     512.1(2)
_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      199(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4930
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1793
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0520
_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)+(0.0795P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                1277
_reflns_number_total             1793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Struct-70.cif
_cod_data_source_block           bi77
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        512.1(3)
_cod_database_code               4508391
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
O1 O 0.6332(3) 0.8376(3) 0.6037(2) 0.0414(6) Uani 1 1 d .
O2 O 0.8628(3) 0.6753(3) 0.3717(2) 0.0432(6) Uani 1 1 d .
H2 H 0.9703 0.6281 0.3048 0.065 Uiso 1 1 calc R
O3 O -0.0922(4) 0.9298(3) 0.7380(2) 0.0507(7) Uani 1 1 d .
O1S O 0.7721(3) 0.9587(3) 0.0991(2) 0.0390(6) Uani 1 1 d .
O4 O 0.3180(4) 0.6197(3) 0.3548(2) 0.0400(6) Uani 1 1 d .
N1 N 0.1135(4) 0.7783(3) 0.5449(2) 0.0300(6) Uani 1 1 d .
H7LH H -0.0063 0.7719 0.5356 0.036 Uiso 1 1 calc R
N2 N 1.3823(4) 0.3508(3) -0.0208(2) 0.0267(6) Uani 1 1 d .
N3 N 0.2751(4) 0.8727(3) 0.6704(2) 0.0304(6) Uani 1 1 d .
H11E H 0.2602 0.9205 0.7446 0.036 Uiso 1 1 calc R
N4 N 1.5537(4) 0.1941(3) -0.0862(3) 0.0334(7) Uani 1 1 d .
H@6 H 1.488(5) 0.143(4) -0.124(3) 0.050 Uiso 1 1 d D
H@4 H 1.646(5) 0.230(4) -0.154(4) 0.050 Uiso 1 1 d D
N5 N 0.6823(4) 0.6588(3) 0.3628(3) 0.0324(6) Uani 1 1 d .
N6 N 1.1424(4) 0.5272(3) 0.1426(3) 0.0359(7) Uani 1 1 d .
C1 C 1.2785(5) 0.5124(4) -0.0709(3) 0.0322(7) Uani 1 1 d .
H0GW H 1.3072 0.5415 -0.1630 0.039 Uiso 1 1 calc R
C2 C 0.5050(4) 0.7248(4) 0.4615(3) 0.0254(7) Uani 1 1 d .
C3 C 0.0864(5) 0.8645(4) 0.6564(3) 0.0299(7) Uani 1 1 d .
N7 N 1.1328(4) 0.6235(3) 0.0244(3) 0.0372(7) Uani 1 1 d .
C5 C 1.2924(5) 0.3657(4) 0.1120(3) 0.0321(7) Uani 1 1 d .
H2GQ H 1.3326 0.2721 0.1742 0.039 Uiso 1 1 calc R
C6 C 0.4842(5) 0.8142(4) 0.5810(3) 0.0271(7) Uani 1 1 d .
C4 C 0.3085(5) 0.7013(4) 0.4468(3) 0.0270(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
N5 O2 H2 109.5
C4 N1 C3 126.4(3)
C4 N1 H7LH 116.8
C3 N1 H7LH 116.8
C1 N2 C5 105.8(2)
C1 N2 N4 130.0(2)
C5 N2 N4 124.2(2)
C6 N3 C3 127.1(2)
C6 N3 H11E 116.5
C3 N3 H11E 116.5
N2 N4 H@6 106(2)
N2 N4 H@4 107(2)
H@6 N4 H@4 107(3)
C2 N5 O2 115.4(2)
C5 N6 N7 107.5(2)
N7 C1 N2 110.6(3)
N7 C1 H0GW 124.7
N2 C1 H0GW 124.7
N5 C2 C6 126.9(3)
N5 C2 C4 113.1(2)
C6 C2 C4 120.0(2)
O3 C3 N1 122.3(3)
O3 C3 N3 121.4(3)
N1 C3 N3 116.3(3)
C1 N7 N6 106.1(2)
N6 C5 N2 109.9(3)
N6 C5 H2GQ 125.0
N2 C5 H2GQ 125.0
O1 C6 N3 119.9(3)
O1 C6 C2 125.4(3)
N3 C6 C2 114.7(3)
O4 C4 N1 121.5(3)
O4 C4 C2 123.2(3)
N1 C4 C2 115.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.210(3)
O2 N5 1.332(3)
O2 H2 0.8400
O3 C3 1.206(4)
O4 C4 1.218(3)
N1 C4 1.370(4)
N1 C3 1.375(4)
N1 H7LH 0.8800
N2 C1 1.345(4)
N2 C5 1.346(4)
N2 N4 1.408(3)
N3 C6 1.375(4)
N3 C3 1.377(4)
N3 H11E 0.8800
N4 H@6 0.92(3)
N4 H@4 0.90(3)
N5 C2 1.295(4)
N6 C5 1.300(4)
N6 N7 1.392(4)
C1 N7 1.304(4)
C1 H0GW 0.9500
C2 C6 1.479(4)
C2 C4 1.492(4)
C5 H2GQ 0.9500
