#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/62/2016262.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_2016262
loop_
_publ_author_name
'Gustavo Portalone'
'Marcello Colapietro'
_publ_section_title
;
 An unusual syn conformation of 5-formyluracil stabilized by
 supramolecular interactions
;
_journal_coeditor_code           HJ3051
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o650
_journal_page_last               o654
_journal_paper_doi               10.1107/S0108270107045659
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H4 N2 O3'
_chemical_formula_moiety         'C5 H4 N2 O3'
_chemical_formula_sum            'C5 H4 N2 O3'
_chemical_formula_weight         140.10
_chemical_melting_point          593
_chemical_name_common            5-Formyluracil
_chemical_name_systematic
;
2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2840(5)
_cell_length_b                   6.7050(6)
_cell_length_c                   12.8302(9)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      15
_cell_volume                     540.59(8)
_computing_cell_refinement       'XCS (Colapietro et al.,  1992)'
_computing_data_collection       'XCS (Colapietro et al.,  1992)'
_computing_data_reduction        'XCS (Colapietro et al.,  1992)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Huber CS single-crystal'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            710
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0792P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                398
_reflns_number_total             413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj3051.cif
_cod_data_source_block           I
_cod_database_code               2016262
_cod_database_fobs_code          2016262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -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
O O1 0.0000 -0.0396(4) -0.0842(3) 0.0638(12) Uani d S 1
O O2 0.0000 0.5820(3) 0.0475(2) 0.0391(8) Uani d S 1
O O7 0.0000 0.6077(4) 0.2715(2) 0.0453(7) Uani d S 1
N N1 0.0000 -0.0102(4) 0.0923(2) 0.0296(6) Uani d S 1
H H1 0.0000 -0.1418 0.1013 0.035 Uiso calc S 1
N N3 0.0000 0.2684(4) -0.0146(2) 0.0331(7) Uani d S 1
H H3 0.0000 0.3198 -0.0785 0.040 Uiso calc S 1
C C2 0.0000 0.0662(4) -0.0081(3) 0.0338(8) Uani d S 1
C C4 0.0000 0.4038(5) 0.0669(2) 0.0280(8) Uani d S 1
C C5 0.0000 0.3117(4) 0.1698(3) 0.0272(6) Uani d S 1
C C6 0.0000 0.1092(4) 0.1763(2) 0.0266(6) Uani d S 1
H H6 0.0000 0.0475 0.2456 0.032 Uiso calc S 1
C C7 0.0000 0.4268(5) 0.2660(3) 0.0338(8) Uani d S 1
H H7 0.0000 0.3523 0.3317 0.041 Uiso calc S 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0302(14) 0.0192(12) 0.0204(12) 0.000 0.000 -0.0039(12)
O2 0.077(2) 0.0104(9) 0.0294(13) 0.000 0.000 0.0012(9)
O7 0.088(2) 0.0215(11) 0.0263(13) 0.000 0.000 -0.0086(10)
N1 0.0578(15) 0.0103(9) 0.0207(12) 0.000 0.000 0.0027(9)
N3 0.0687(19) 0.0137(10) 0.0168(11) 0.000 0.000 0.0020(9)
C2 0.069(2) 0.0140(12) 0.0185(16) 0.000 0.000 -0.0006(11)
C4 0.050(2) 0.0118(11) 0.0223(17) 0.000 0.000 0.0005(10)
C5 0.0473(16) 0.0155(11) 0.0189(12) 0.000 0.000 -0.0001(11)
C6 0.0463(16) 0.0162(12) 0.0172(13) 0.000 0.000 -0.0009(10)
C7 0.062(2) 0.0184(14) 0.0205(14) 0.000 0.000 -0.0033(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N1 C2 121.7(3)
C6 N1 H1 119.1
C2 N1 H1 119.1
C2 N3 C4 127.5(3)
C2 N3 H3 116.3
C4 N3 H3 116.3
O1 C2 N3 122.5(3)
O1 C2 N1 122.3(3)
N3 C2 N1 115.2(3)
O2 C4 N3 119.2(3)
O2 C4 C5 126.8(3)
N3 C4 C5 114.0(3)
C6 C5 C7 118.5(3)
C6 C5 C4 118.6(3)
C7 C5 C4 122.9(3)
N1 C6 C5 123.1(3)
N1 C6 H6 118.5
C5 C6 H6 118.5
O7 C7 C5 125.3(3)
O7 C7 H7 117.3
C5 C7 H7 117.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.207(4)
O2 C4 1.220(3)
O7 C7 1.215(4)
N1 C6 1.343(4)
N1 C2 1.386(4)
N1 H1 0.8900
N3 C2 1.358(4)
N3 C4 1.384(4)
N3 H3 0.8900
C4 C5 1.458(4)
C5 C6 1.360(3)
C5 C7 1.456(5)
C6 H6 0.9800
C7 H7 0.9800
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 O2 1_545 0.89 1.98 2.794(3) 152.1
N1 H1 O7 1_545 0.89 2.75 3.442(4) 135.0
N3 H3 O7 2_564 0.89 1.99 2.868(4) 171.4
C6 H6 O1 2 0.98 2.18 3.108(5) 156.5
C7 H7 O1 2 0.98 2.36 3.231(5) 147.9
C7 H7 O2 2_565 0.98 2.80 3.613(5) 140.3
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
C4 N3 C2 O1 180.0
C4 N3 C2 N1 0.0
C6 N1 C2 O1 180.0
C6 N1 C2 N3 0.0
C2 N3 C4 O2 180.0
C2 N3 C4 C5 0.0
O2 C4 C5 C6 180.0
N3 C4 C5 C6 0.0
O2 C4 C5 C7 0.0
N3 C4 C5 C7 180.0
C2 N1 C6 C5 0.0
C7 C5 C6 N1 180.0
C4 C5 C6 N1 0.0
C6 C5 C7 O7 180.0
C4 C5 C7 O7 0.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 269368
