#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017669.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_2017669
loop_
_publ_author_name
'Portalone, Gustavo'
_publ_section_title
;
 Supramolecular association in proton-transfer adducts containing
 benzamidinium cations. I. Four molecular salts with uracil derivatives
;
_journal_coeditor_code           FN3053
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o295
_journal_page_last               o301
_journal_paper_doi               10.1107/S0108270110016252
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H9 N2 + , C4 H2 N3 O4 -'
_chemical_formula_moiety         'C7 H9 N2 + , C4 H2 N3 O4 -'
_chemical_formula_sum            'C11 H11 N5 O4'
_chemical_formula_weight         277.25
_chemical_name_common
;
benzamidinidium 5-nitrouracilate
;
_chemical_name_systematic
;
benzamidinidium 5-nitro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ide
;
_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           SHELXL97
_cell_angle_alpha                78.551(7)
_cell_angle_beta                 86.841(8)
_cell_angle_gamma                84.051(7)
_cell_formula_units_Z            2
_cell_length_a                   4.3625(4)
_cell_length_b                   10.4461(11)
_cell_length_c                   13.8556(12)
_cell_measurement_reflns_used    2451
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.6885
_cell_measurement_theta_min      2.7051
_cell_volume                     615.13(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Oxford Xcalibur S CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4864
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2006); empirical absorption
correction
using spherical harmonics implemented in the SCALE3 ABSPACK scaling algorithm]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0508
_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)+(0.0590P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                1427
_reflns_number_total             2153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3053.cif
_cod_data_source_block           IV
_cod_database_code               2017669
_cod_database_fobs_code          2017669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1899(4) 0.68872(17) 0.01314(12) 0.0498(5) Uani d . 1 . .
O O2 0.7422(4) 0.98092(16) 0.10665(12) 0.0491(5) Uani d . 1 . .
O O3 1.0469(4) 0.88810(18) 0.27942(13) 0.0562(5) Uani d . 1 . .
O O4 1.0080(5) 0.68823(18) 0.34994(13) 0.0622(6) Uani d . 1 . .
N N1 0.4511(5) 0.61358(19) 0.15366(15) 0.0427(6) Uani d . 1 . .
C C2 0.3644(5) 0.7085(2) 0.07448(17) 0.0358(6) Uani d . 1 . .
N N3 0.4734(4) 0.82919(19) 0.06400(15) 0.0361(5) Uani d . 1 . .
H H3 0.414(6) 0.890(3) 0.009(2) 0.065(9) Uiso d . 1 . .
C C4 0.6652(5) 0.8690(2) 0.12624(17) 0.0345(6) Uani d . 1 . .
C C5 0.7458(5) 0.7654(2) 0.20896(16) 0.0316(5) Uani d . 1 . .
C C6 0.6324(5) 0.6451(2) 0.21636(17) 0.0387(6) Uani d . 1 . .
H H6 0.6918 0.5778 0.2729 0.046 Uiso calc R 1 . .
N N7 0.9421(5) 0.7824(2) 0.28300(14) 0.0401(5) Uani d . 1 . .
N N4 -0.1471(6) 0.6134(2) -0.13726(18) 0.0525(7) Uani d . 1 . .
H H4A -0.040(7) 0.603(3) -0.080(2) 0.082(10) Uiso d . 1 . .
H H4B -0.244(5) 0.550(3) -0.1495(18) 0.048(8) Uiso d . 1 . .
N N5 -0.0940(5) 0.8307(2) -0.16192(18) 0.0453(6) Uani d . 1 . .
H H5A -0.001(6) 0.817(3) -0.104(2) 0.056(8) Uiso d . 1 . .
H H5B -0.092(6) 0.906(3) -0.201(2) 0.050(8) Uiso d . 1 . .
C C8 -0.3422(5) 0.7507(2) -0.28649(16) 0.0369(6) Uani d . 1 . .
C C9 -0.5120(6) 0.8683(3) -0.32222(18) 0.0469(7) Uani d . 1 . .
H H9 -0.5297 0.9381 -0.2848 0.056 Uiso calc R 1 . .
C C10 -0.6557(7) 0.8869(3) -0.4105(2) 0.0646(9) Uani d . 1 . .
H H10 -0.7773 0.9691 -0.4345 0.078 Uiso calc R 1 . .
C C11 -0.6273(8) 0.7896(4) -0.4643(2) 0.0732(10) Uani d . 1 . .
H H11 -0.7278 0.8035 -0.5268 0.088 Uiso calc R 1 . .
C C12 -0.4575(8) 0.6725(4) -0.4308(2) 0.0733(10) Uani d . 1 . .
H H12 -0.4367 0.6044 -0.4698 0.088 Uiso calc R 1 . .
C C13 -0.3150(7) 0.6514(3) -0.34063(19) 0.0526(7) Uani d . 1 . .
H H13 -0.1981 0.5683 -0.3160 0.063 Uiso calc R 1 . .
C C14 -0.1896(5) 0.7313(2) -0.19131(17) 0.0352(6) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 117.3(2) ?
O1 C2 N1 . . 121.8(2) ?
O1 C2 N3 . . 119.5(2) ?
N1 C2 N3 . . 118.7(2) ?
C2 N3 C4 . . 127.2(2) ?
C2 N3 H3 . . 116.2(17) ?
C4 N3 H3 . . 116.6(17) ?
O2 C4 N3 . . 119.4(2) ?
O2 C4 C5 . . 129.0(2) ?
N3 C4 C5 . . 111.6(2) ?
C6 C5 N7 . . 118.6(2) ?
C6 C5 C4 . . 119.3(2) ?
N7 C5 C4 . . 122.11(19) ?
N1 C6 C5 . . 125.9(2) ?
N1 C6 H6 . . 117.1 ?
C5 C6 H6 . . 117.1 ?
O3 N7 O4 . . 120.94(19) ?
O3 N7 C5 . . 120.62(19) ?
O4 N7 C5 . . 118.43(19) ?
C14 N4 H4A . . 118.3(19) ?
C14 N4 H4B . . 120.2(17) ?
H4A N4 H4B . . 121(2) ?
C14 N5 H5A . . 118.8(17) ?
C14 N5 H5B . . 120.8(17) ?
H5A N5 H5B . . 120(2) ?
C9 C8 C13 . . 119.6(2) ?
C9 C8 C14 . . 120.1(2) ?
C13 C8 C14 . . 120.3(2) ?
C10 C9 C8 . . 120.4(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C11 C10 C9 . . 120.0(3) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.5(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C13 . . 120.0(3) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C8 C13 C12 . . 119.3(3) ?
C8 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
N5 C14 N4 . . 120.1(2) ?
N5 C14 C8 . . 120.2(2) ?
N4 C14 C8 . . 119.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.232(3) ?
O2 C4 . 1.224(3) ?
O3 N7 . 1.229(2) ?
O4 N7 . 1.232(2) ?
N1 C6 . 1.316(3) ?
N1 C2 . 1.366(3) ?
C2 N3 . 1.371(3) ?
N3 C4 . 1.382(3) ?
N3 H3 . 0.92(3) ?
C4 C5 . 1.443(3) ?
C5 C6 . 1.381(3) ?
C5 N7 . 1.421(3) ?
C6 H6 . 0.9700 ?
N4 C14 . 1.309(3) ?
N4 H4A . 0.92(3) ?
N4 H4B . 0.87(3) ?
N5 C14 . 1.302(3) ?
N5 H5A . 0.89(3) ?
N5 H5B . 0.86(3) ?
C8 C9 . 1.384(3) ?
C8 C13 . 1.387(4) ?
C8 C14 . 1.478(3) ?
C9 C10 . 1.375(4) ?
C9 H9 . 0.9700 ?
C10 C11 . 1.368(4) ?
C10 H10 . 0.9700 ?
C11 C12 . 1.373(5) ?
C11 H11 . 0.9700 ?
C12 C13 . 1.394(4) ?
C12 H12 . 0.9700 ?
C13 H13 . 0.9700 ?
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
N3 H3 O2 2_675 0.92(3) 1.98(3) 2.899(2) 176(2)
N4 H4A O1 . 0.92(3) 2.07(3) 2.890(3) 148(3)
N4 H4B N1 2_565 0.87(3) 2.03(3) 2.886(3) 170(2)
N5 H5A O1 . 0.89(3) 2.05(3) 2.853(3) 149(2)
N5 H5B O3 2_675 0.86(3) 2.23(3) 3.084(3) 169(2)
C9 H9 O2 2_575 0.97 2.84 3.691(3) 146.5
C11 H11 O4 1_354 0.97 2.65 3.487(3) 144.9
C13 H13 O4 2_665 0.97 2.84 3.685(4) 145.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 O1 . . . . -178.4(2) ?
C6 N1 C2 N3 . . . . 1.0(4) ?
O1 C2 N3 C4 . . . . 178.8(2) ?
N1 C2 N3 C4 . . . . -0.6(4) ?
C2 N3 C4 O2 . . . . -179.9(3) ?
C2 N3 C4 C5 . . . . -0.1(3) ?
O2 C4 C5 C6 . . . . -179.8(3) ?
N3 C4 C5 C6 . . . . 0.5(3) ?
O2 C4 C5 N7 . . . . -0.5(4) ?
N3 C4 C5 N7 . . . . 179.7(2) ?
C2 N1 C6 C5 . . . . -0.6(4) ?
N7 C5 C6 N1 . . . . -179.4(2) ?
C4 C5 C6 N1 . . . . -0.1(4) ?
C6 C5 N7 O3 . . . . -179.7(2) ?
C4 C5 N7 O3 . . . . 1.1(3) ?
C6 C5 N7 O4 . . . . 1.3(3) ?
C4 C5 N7 O4 . . . . -177.9(2) ?
C13 C8 C9 C10 . . . . 0.6(4) ?
C14 C8 C9 C10 . . . . -179.7(2) ?
C8 C9 C10 C11 . . . . -1.1(4) ?
C9 C10 C11 C12 . . . . 0.5(5) ?
C10 C11 C12 C13 . . . . 0.7(5) ?
C9 C8 C13 C12 . . . . 0.6(4) ?
C14 C8 C13 C12 . . . . -179.2(2) ?
C11 C12 C13 C8 . . . . -1.2(4) ?
C9 C8 C14 N5 . . . . -30.4(3) ?
C13 C8 C14 N5 . . . . 149.3(2) ?
C9 C8 C14 N4 . . . . 150.6(2) ?
C13 C8 C14 N4 . . . . -29.7(4) ?
