#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017668.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_2017668
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 O5 - , 2H2 O'
_chemical_formula_moiety         'C7 H9 N2 + , C4 H2 N3 O5 - , 2H2 O'
_chemical_formula_sum            'C11 H15 N5 O7'
_chemical_formula_weight         329.28
_chemical_name_common
;
benzamidinium diliturate dihydrate
;
_chemical_name_systematic
;
benzamidinium 5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 98.2485(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7607(3)
_cell_length_b                   5.0998(2)
_cell_length_c                   27.2412(5)
_cell_measurement_reflns_used    109123
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      32.6648
_cell_measurement_theta_min      2.9968
_cell_volume                     1479.46(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Xcalibur S CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            306312
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.99102
_exptl_absorpt_correction_T_min  0.90782
_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    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0642
_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)+(0.0635P)²+0.6910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                4542
_reflns_number_total             5116
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3053.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017668
_cod_database_fobs_code          2017668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.20675(11) 1.0305(3) 1.05258(5) 0.0443(3) Uani d . 1 . .
O O2 0.08156(10) 0.3367(2) 0.95529(4) 0.0362(3) Uani d . 1 . .
O O3 0.23715(13) 0.1631(3) 0.89742(6) 0.0590(4) Uani d . 1 . .
O O4 0.41060(14) 0.3588(3) 0.89454(7) 0.0695(5) Uani d . 1 . .
O O5 0.48272(10) 0.7389(3) 0.95592(5) 0.0435(3) Uani d . 1 . .
N N1 0.34360(11) 0.8703(3) 1.00466(5) 0.0322(3) Uani d . 1 . .
H H1 0.400(2) 0.994(5) 1.0182(8) 0.047(6) Uiso d . 1 . .
C C2 0.23149(13) 0.8694(3) 1.02225(5) 0.0296(3) Uani d . 1 . .
N N3 0.14927(11) 0.6774(3) 1.00394(5) 0.0313(3) Uani d . 1 . .
H H3 0.078(2) 0.674(5) 1.0176(8) 0.052(6) Uiso d . 1 . .
C C4 0.16764(12) 0.4934(3) 0.96836(5) 0.0262(3) Uani d . 1 . .
C C5 0.28619(12) 0.5111(3) 0.94975(5) 0.0262(3) Uani d . 1 . .
C C6 0.37880(13) 0.7058(3) 0.96863(5) 0.0290(3) Uani d . 1 . .
N N7 0.31216(11) 0.3390(3) 0.91275(5) 0.0331(3) Uani d . 1 . .
N N4 -0.00024(13) -0.1025(3) 0.89387(5) 0.0336(3) Uani d . 1 . .
H H4A 0.057(2) 0.007(4) 0.9031(8) 0.046(6) Uiso d . 1 . .
H H4B -0.068(2) -0.102(4) 0.9086(8) 0.045(5) Uiso d . 1 . .
N N5 0.11348(14) -0.2591(3) 0.83616(6) 0.0442(4) Uani d . 1 . .
H H5A 0.172(2) -0.151(5) 0.8455(9) 0.057(7) Uiso d . 1 . .
H H5B 0.126(2) -0.373(5) 0.8130(9) 0.053(6) Uiso d . 1 . .
C C8 -0.08858(13) -0.4616(3) 0.84180(5) 0.0283(3) Uani d . 1 . .
C C9 -0.07573(16) -0.6385(3) 0.80398(6) 0.0378(3) Uani d . 1 . .
H H9 -0.0013 -0.6339 0.7877 0.045 Uiso calc R 1 . .
C C10 -0.16936(18) -0.8218(3) 0.78951(6) 0.0434(4) Uani d . 1 . .
H H10 -0.1598 -0.9446 0.7631 0.052 Uiso calc R 1 . .
C C11 -0.27553(17) -0.8307(3) 0.81227(6) 0.0427(4) Uani d . 1 . .
H H11 -0.3403 -0.9600 0.8022 0.051 Uiso calc R 1 . .
C C12 -0.28899(18) -0.6554(4) 0.84935(7) 0.0480(4) Uani d . 1 . .
H H12 -0.3639 -0.6607 0.8653 0.058 Uiso calc R 1 . .
C C13 -0.19668(17) -0.4708(4) 0.86416(7) 0.0437(4) Uani d . 1 . .
H H13 -0.2076 -0.3473 0.8903 0.052 Uiso calc R 1 . .
C C14 0.01158(13) -0.2672(3) 0.85800(5) 0.0294(3) Uani d . 1 . .
O O6 0.4502(2) -0.1249(5) 0.84345(7) 0.0746(5) Uani d . 1 . .
H H61 0.443(4) 0.013(9) 0.8638(16) 0.121(14) Uiso d . 1 . .
H H62 0.454(4) -0.244(9) 0.8614(15) 0.115(15) Uiso d . 1 . .
O O7 0.31408(19) -0.0585(4) 0.75176(8) 0.0674(5) Uani d . 1 . .
H H71 0.363(3) -0.087(7) 0.7806(12) 0.082(10) Uiso d . 1 . .
H H72 0.272(4) -0.203(9) 0.7466(15) 0.112(13) Uiso 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
C2 N1 C6 . . 126.45(11) ?
C2 N1 H1 . . 115.4(14) ?
C6 N1 H1 . . 118.1(14) ?
O1 C2 N1 . . 121.76(12) ?
O1 C2 N3 . . 122.48(13) ?
N1 C2 N3 . . 115.76(12) ?
C2 N3 C4 . . 126.32(12) ?
C2 N3 H3 . . 114.1(15) ?
C4 N3 H3 . . 119.6(16) ?
O2 C4 N3 . . 117.62(12) ?
O2 C4 C5 . . 127.13(12) ?
N3 C4 C5 . . 115.24(11) ?
N7 C5 C4 . . 119.59(11) ?
N7 C5 C6 . . 119.28(11) ?
C4 C5 C6 . . 121.12(11) ?
O5 C6 N1 . . 117.96(12) ?
O5 C6 C5 . . 127.02(13) ?
N1 C6 C5 . . 115.02(12) ?
O4 N7 O3 . . 118.56(13) ?
O4 N7 C5 . . 120.71(12) ?
O3 N7 C5 . . 120.73(12) ?
C14 N4 H4A . . 120.1(15) ?
C14 N4 H4B . . 121.1(15) ?
H4A N4 H4B . . 119(2) ?
C14 N5 H5A . . 121.0(17) ?
C14 N5 H5B . . 121.8(16) ?
H5A N5 H5B . . 117(2) ?
C13 C8 C9 . . 118.77(13) ?
C13 C8 C14 . . 120.68(13) ?
C9 C8 C14 . . 120.55(13) ?
C10 C9 C8 . . 120.09(16) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C11 C10 C9 . . 120.63(15) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.48(15) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.67(17) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.37(15) ?
C12 C13 H13 . . 119.8 ?
C8 C13 H13 . . 119.8 ?
N4 C14 N5 . . 119.49(14) ?
N4 C14 C8 . . 120.43(13) ?
N5 C14 C8 . . 120.07(13) ?
H61 O6 H62 . . 103(4) ?
H71 O7 H72 . . 104(3) ?
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 . 1.2215(18) ?
O2 C4 . 1.2364(16) ?
O3 N7 . 1.2385(16) ?
O4 N7 . 1.2364(17) ?
O5 C6 . 1.2287(17) ?
N1 C2 . 1.3605(18) ?
N1 C6 . 1.3848(18) ?
N1 H1 . 0.91(2) ?
C2 N3 . 1.3652(17) ?
N3 C4 . 1.3835(17) ?
N3 H3 . 0.90(2) ?
C4 C5 . 1.4416(18) ?
C5 N7 . 1.3945(17) ?
C5 C6 . 1.4478(17) ?
N4 C14 . 1.3083(19) ?
N4 H4A . 0.84(2) ?
N4 H4B . 0.88(2) ?
N5 C14 . 1.321(2) ?
N5 H5A . 0.85(3) ?
N5 H5B . 0.88(3) ?
C8 C13 . 1.389(2) ?
C8 C9 . 1.391(2) ?
C8 C14 . 1.4843(19) ?
C9 C10 . 1.389(2) ?
C9 H9 . 0.9700 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9700 ?
C11 C12 . 1.372(3) ?
C11 H11 . 0.9700 ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.9700 ?
C13 H13 . 0.9700 ?
O6 H61 . 0.91(5) ?
O6 H62 . 0.78(4) ?
O7 H71 . 0.89(3) ?
O7 H72 . 0.87(4) ?
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 O5 3_677 0.91(2) 1.92(2) 2.8359(16) 178(2)
N3 H3 O2 3_567 0.90(2) 1.97(2) 2.8635(16) 178(2)
N4 H4A O2 . 0.84(2) 2.19(2) 2.8581(16) 135.5(19)
N4 H4A O3 . 0.84(2) 2.12(2) 2.8808(18) 150(2)
N4 H4B O1 3_567 0.88(2) 1.98(2) 2.8514(18) 168(2)
N5 H5A O3 . 0.85(3) 2.19(3) 2.9250(19) 146(2)
N5 H5B O7 2_546 0.88(3) 2.18(3) 3.035(2) 164(2)
O6 H61 O4 . 0.91(5) 2.00(5) 2.894(2) 167(4)
O6 H62 O4 1_545 0.78(4) 2.29(4) 3.037(3) 160(4)
O7 H71 O6 . 0.89(3) 1.84(3) 2.729(3) 173(3)
O7 H72 O7 2_546 0.87(4) 2.04(4) 2.8940(19) 169(4)
C9 H9 O7 2_546 0.97 2.45 3.410(2) 172.3
C13 H13 O1 3_567 0.97 2.24 3.204(2) 171.1
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 . . . . -176.59(16) ?
C6 N1 C2 N3 . . . . 3.5(2) ?
O1 C2 N3 C4 . . . . 177.54(15) ?
N1 C2 N3 C4 . . . . -2.6(2) ?
C2 N3 C4 O2 . . . . -178.44(15) ?
C2 N3 C4 C5 . . . . 0.2(2) ?
O2 C4 C5 N7 . . . . 0.3(2) ?
N3 C4 C5 N7 . . . . -178.20(13) ?
O2 C4 C5 C6 . . . . 180.00(15) ?
N3 C4 C5 C6 . . . . 1.5(2) ?
C2 N1 C6 O5 . . . . 177.73(15) ?
C2 N1 C6 C5 . . . . -2.0(2) ?
N7 C5 C6 O5 . . . . -0.7(2) ?
C4 C5 C6 O5 . . . . 179.63(16) ?
N7 C5 C6 N1 . . . . 178.97(13) ?
C4 C5 C6 N1 . . . . -0.7(2) ?
C4 C5 N7 O4 . . . . 176.48(17) ?
C6 C5 N7 O4 . . . . -3.2(2) ?
C4 C5 N7 O3 . . . . -3.5(2) ?
C6 C5 N7 O3 . . . . 176.81(16) ?
C13 C8 C9 C10 . . . . -0.7(2) ?
C14 C8 C9 C10 . . . . 179.22(15) ?
C8 C9 C10 C11 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C10 C11 C12 C13 . . . . -0.3(3) ?
C11 C12 C13 C8 . . . . -0.4(3) ?
C9 C8 C13 C12 . . . . 0.8(3) ?
C14 C8 C13 C12 . . . . -179.05(17) ?
C13 C8 C14 N4 . . . . 0.5(2) ?
C9 C8 C14 N4 . . . . -179.40(15) ?
C13 C8 C14 N5 . . . . -179.46(17) ?
C9 C8 C14 N5 . . . . 0.7(2) ?
