#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017667.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_2017667
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 + , C5 H3 N2 O4 - , 3H2 O'
_chemical_formula_moiety         'C7 H9 N2 + , C5 H3 N2 O4 - , 3H2 O'
_chemical_formula_sum            'C12 H18 N4 O7'
_chemical_formula_weight         330.30
_chemical_name_common
;
benzamidinium isoorotate trihydrate
;
_chemical_name_systematic
;
benzamidinium 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate trihydrate
;
_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                 96.221(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3562(2)
_cell_length_b                   6.04020(10)
_cell_length_c                   22.3763(4)
_cell_measurement_reflns_used    39574
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      32.5607
_cell_measurement_theta_min      2.6837
_cell_volume                     1525.84(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            218566
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.990021
_exptl_absorpt_correction_T_min  0.918007
_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    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0865
_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)+(0.0799P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                3884
_reflns_number_total             5260
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3053.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017667
_cod_database_fobs_code          2017667
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 0.26236(11) 1.4201(2) -0.03821(6) 0.0409(3) Uani d . 1 . .
O O2 0.43826(10) 0.8013(2) 0.04372(6) 0.0398(3) Uani d . 1 . .
O O3 0.29919(13) 0.5324(3) 0.11227(8) 0.0589(5) Uani d . 1 . .
O O4 0.12458(11) 0.6721(2) 0.12812(6) 0.0427(4) Uani d . 1 . .
N N1 0.15370(12) 1.1941(3) 0.01643(7) 0.0358(4) Uani d . 1 . .
H H1 0.094(2) 1.297(4) 0.0115(11) 0.060(7) Uiso d . 1 . .
C C2 0.25451(14) 1.2515(3) -0.00842(8) 0.0308(4) Uani d . 1 . .
N N3 0.34525(12) 1.1024(3) 0.00255(7) 0.0309(3) Uani d . 1 . .
H H3 0.410(2) 1.136(4) -0.0146(11) 0.053(7) Uiso d . 1 . .
C C4 0.34696(13) 0.9121(3) 0.03751(7) 0.0273(3) Uani d . 1 . .
C C5 0.23792(13) 0.8678(3) 0.06406(7) 0.0282(4) Uani d . 1 . .
C C6 0.14801(14) 1.0140(3) 0.05187(8) 0.0319(4) Uani d . 1 . .
H H6 0.0751 0.9878 0.0697 0.038 Uiso calc R 1 . .
C C7 0.22149(15) 0.6745(3) 0.10440(8) 0.0330(4) Uani d . 1 . .
N N4 0.53366(15) 0.3845(3) 0.09913(8) 0.0374(4) Uani d . 1 . .
H H4A 0.470(2) 0.479(4) 0.0904(12) 0.060(7) Uiso d . 1 . .
H H4B 0.592(2) 0.408(4) 0.0797(11) 0.055(7) Uiso d . 1 . .
N N5 0.43814(15) 0.1995(3) 0.16819(8) 0.0418(4) Uani d . 1 . .
H H5A 0.376(2) 0.293(4) 0.1573(12) 0.060(7) Uiso d . 1 . .
H H5B 0.442(2) 0.101(4) 0.1975(11) 0.049(6) Uiso d . 1 . .
C C8 0.63617(15) 0.0799(3) 0.15370(7) 0.0298(4) Uani d . 1 . .
C C9 0.62272(17) -0.1276(3) 0.17948(9) 0.0375(4) Uani d . 1 . .
H H9 0.5449 -0.1784 0.1874 0.045 Uiso calc R 1 . .
C C10 0.7211(2) -0.2612(3) 0.19376(9) 0.0441(5) Uani d . 1 . .
H H10 0.7119 -0.4045 0.2122 0.053 Uiso calc R 1 . .
C C11 0.83168(19) -0.1922(4) 0.18196(10) 0.0491(5) Uani d . 1 . .
H H11 0.8999 -0.2874 0.1916 0.059 Uiso calc R 1 . .
C C12 0.84547(19) 0.0126(4) 0.15639(11) 0.0500(6) Uani d . 1 . .
H H12 0.9236 0.0613 0.1483 0.060 Uiso calc R 1 . .
C C13 0.74854(17) 0.1489(3) 0.14223(9) 0.0397(4) Uani d . 1 . .
H H13 0.7589 0.2928 0.1243 0.048 Uiso calc R 1 . .
C C14 0.53215(15) 0.2267(3) 0.13968(8) 0.0294(4) Uani d . 1 . .
O O5 -0.03586(15) 0.3885(3) 0.06362(8) 0.0550(5) Uani d . 1 . .
H H51 0.003(3) 0.499(6) 0.0845(17) 0.110(14) Uiso d . 1 . .
H H52 -0.102(3) 0.447(5) 0.0593(13) 0.068(8) Uiso d . 1 . .
O O6 0.1476(2) 0.9933(3) 0.22115(11) 0.0669(5) Uani d . 1 . .
H H61 0.135(3) 0.901(6) 0.1891(16) 0.089(11) Uiso d . 1 . .
H H62 0.217(4) 0.975(6) 0.2296(18) 0.100(14) Uiso d . 1 . .
O O7 0.10895(17) 0.4328(3) 0.23105(8) 0.0546(4) Uani d . 1 . .
H H71 0.114(3) 0.497(5) 0.1971(15) 0.075(9) Uiso d . 1 . .
H H72 0.112(2) 0.297(5) 0.2232(12) 0.064(8) 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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 122.46(14) ?
C6 N1 H1 . . 122.1(16) ?
C2 N1 H1 . . 114.9(16) ?
O1 C2 N1 . . 122.97(15) ?
O1 C2 N3 . . 123.09(15) ?
N1 C2 N3 . . 113.94(16) ?
C2 N3 C4 . . 127.51(14) ?
C2 N3 H3 . . 114.6(15) ?
C4 N3 H3 . . 117.9(15) ?
O2 C4 N3 . . 118.31(14) ?
O2 C4 C5 . . 126.76(16) ?
N3 C4 C5 . . 114.93(13) ?
C6 C5 C4 . . 117.00(15) ?
C6 C5 C7 . . 119.23(14) ?
C4 C5 C7 . . 123.76(14) ?
N1 C6 C5 . . 124.03(15) ?
N1 C6 H6 . . 118.0 ?
C5 C6 H6 . . 118.0 ?
O3 C7 O4 . . 124.90(17) ?
O3 C7 C5 . . 119.68(15) ?
O4 C7 C5 . . 115.42(15) ?
C14 N4 H4A . . 121.6(16) ?
C14 N4 H4B . . 123.2(17) ?
H4A N4 H4B . . 115(2) ?
C14 N5 H5A . . 115.9(16) ?
C14 N5 H5B . . 118.0(15) ?
H5A N5 H5B . . 126(2) ?
C13 C8 C9 . . 119.25(16) ?
C13 C8 C14 . . 120.47(16) ?
C9 C8 C14 . . 120.27(15) ?
C10 C9 C8 . . 119.76(18) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C11 C10 C9 . . 120.6(2) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 119.90(19) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C13 . . 120.4(2) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C12 C13 C8 . . 120.12(19) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
N5 C14 N4 . . 119.82(17) ?
N5 C14 C8 . . 119.61(16) ?
N4 C14 C8 . . 120.57(16) ?
H51 O5 H52 . . 98(3) ?
H61 O6 H62 . . 100(3) ?
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 . 1.225(2) ?
O2 C4 . 1.2293(19) ?
O3 C7 . 1.230(2) ?
O4 C7 . 1.273(2) ?
N1 C6 . 1.352(2) ?
N1 C2 . 1.370(2) ?
N1 H1 . 0.92(3) ?
C2 N3 . 1.371(2) ?
N3 C4 . 1.389(2) ?
N3 H3 . 0.89(3) ?
C4 C5 . 1.455(2) ?
C5 C6 . 1.355(2) ?
C5 C7 . 1.500(2) ?
C6 H6 . 0.9700 ?
N4 C14 . 1.318(2) ?
N4 H4A . 0.92(3) ?
N4 H4B . 0.84(3) ?
N5 C14 . 1.312(2) ?
N5 H5A . 0.92(3) ?
N5 H5B . 0.88(3) ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.395(3) ?
C8 C14 . 1.483(2) ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.9700 ?
C10 C11 . 1.376(3) ?
C10 H10 . 0.9700 ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.9700 ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.9700 ?
C13 H13 . 0.9700 ?
O5 H51 . 0.90(4) ?
O5 H52 . 0.83(3) ?
O6 H61 . 0.91(4) ?
O6 H62 . 0.80(4) ?
O7 H71 . 0.86(3) ?
O7 H72 . 0.84(3) ?
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 1_565 0.92(3) 2.05(3) 2.760(2) 133(2)
N3 H3 O2 3_675 0.89(3) 1.95(3) 2.8296(18) 174(2)
N4 H4A O2 . 0.92(3) 2.22(3) 2.959(2) 136(2)
N4 H4A O3 . 0.92(3) 2.08(3) 2.854(2) 141(2)
N4 H4B O1 3_675 0.84(3) 2.24(3) 3.050(2) 162(2)
N5 H5A O3 . 0.92(3) 1.92(3) 2.770(2) 154(2)
N5 H5B O7 2_545 0.88(3) 2.03(3) 2.868(2) 158(2)
O5 H51 O4 . 0.90(4) 1.91(4) 2.787(2) 163(3)
O5 H52 O1 3_575 0.83(3) 2.00(3) 2.821(2) 173(3)
O6 H61 O4 . 0.91(4) 1.94(4) 2.837(3) 171(3)
O6 H62 O7 2 0.80(4) 2.09(4) 2.878(3) 169(4)
O7 H71 O4 . 0.86(3) 1.89(3) 2.741(2) 173(3)
O7 H72 O6 1_545 0.84(3) 1.88(3) 2.704(3) 166(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_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 . . . . -176.40(18) ?
C6 N1 C2 N3 . . . . 4.2(3) ?
O1 C2 N3 C4 . . . . 177.21(17) ?
N1 C2 N3 C4 . . . . -3.4(3) ?
C2 N3 C4 O2 . . . . -177.76(17) ?
C2 N3 C4 C5 . . . . 1.3(3) ?
O2 C4 C5 C6 . . . . 179.15(18) ?
N3 C4 C5 C6 . . . . 0.2(2) ?
O2 C4 C5 C7 . . . . 0.4(3) ?
N3 C4 C5 C7 . . . . -178.60(16) ?
C2 N1 C6 C5 . . . . -3.2(3) ?
C4 C5 C6 N1 . . . . 0.8(3) ?
C7 C5 C6 N1 . . . . 179.63(17) ?
C6 C5 C7 O3 . . . . 174.78(19) ?
C4 C5 C7 O3 . . . . -6.5(3) ?
C6 C5 C7 O4 . . . . -5.0(3) ?
C4 C5 C7 O4 . . . . 173.72(16) ?
C13 C8 C9 C10 . . . . 0.6(3) ?
C14 C8 C9 C10 . . . . -178.41(18) ?
C8 C9 C10 C11 . . . . -0.9(3) ?
C9 C10 C11 C12 . . . . 0.8(3) ?
C10 C11 C12 C13 . . . . -0.3(4) ?
C11 C12 C13 C8 . . . . 0.0(3) ?
C9 C8 C13 C12 . . . . -0.1(3) ?
C14 C8 C13 C12 . . . . 178.89(19) ?
C13 C8 C14 N5 . . . . -156.43(19) ?
C9 C8 C14 N5 . . . . 22.5(3) ?
C13 C8 C14 N4 . . . . 23.2(3) ?
C9 C8 C14 N4 . . . . -157.83(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654241
