#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/14/2231461.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_2231461
loop_
_publ_author_name
'Booysen, Irvin'
'Ismail, Muhammed'
'Gerber, Thomas'
'Hosten, Eric'
'Betz, Richard'
_publ_section_title
;
 2-[(E)-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iminomethyl]pyridinium
 chloride monohydrate
;
_journal_coeditor_code           DN2714
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2436
_journal_page_last               o2437
_journal_paper_doi               10.1107/S1600536811033307
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H14 N5 O2 +, Cl -, H2 O'
_chemical_formula_moiety         'C12 H14 N5 O2 +, Cl -, H2 O'
_chemical_formula_sum            'C12 H16 Cl N5 O3'
_chemical_formula_weight         313.75
_chemical_name_systematic
'2-[(E)-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iminomethyl]pyridinium chloride monohydrate'
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3797(4)
_cell_length_b                   15.7975(5)
_cell_length_c                   12.9998(4)
_cell_measurement_reflns_used    5575
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.54
_cell_volume                     2747.71(15)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24436
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0424
_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)+(0.0549P)²+0.7712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2327
_reflns_number_total             3415
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2714.cif
_cod_data_source_block           I
_cod_database_code               2231461
_cod_database_fobs_code          2231461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_symmetry_multiplicity
O O1 0.75612(9) -0.02776(9) 0.13036(10) 0.0310(3) Uani d . 1 1
O O2 0.43377(9) -0.11801(8) 0.12425(10) 0.0282(3) Uani d . 1 1
N N1 0.63382(10) 0.07221(9) 0.12603(11) 0.0222(3) Uani d . 1 1
N N2 0.59510(11) -0.07228(9) 0.13227(11) 0.0224(3) Uani d . 1 1
N N3 0.36366(10) 0.05754(9) 0.12000(11) 0.0201(3) Uani d . 1 1
N N4 0.51074(12) 0.17487(10) 0.11875(13) 0.0260(3) Uani d . 1 1
H H741 0.5501(17) 0.2148(14) 0.1230(14) 0.026(5) Uiso d . 1 1
H H742 0.4432(19) 0.1906(15) 0.1194(16) 0.040(6) Uiso d . 1 1
N N5 0.18069(11) 0.13375(9) 0.11007(12) 0.0246(3) Uani d . 1 1
H H751 0.2352(17) 0.1666(15) 0.1123(15) 0.034(6) Uiso d . 1 1
C C1 0.46118(12) 0.02987(11) 0.12260(12) 0.0194(3) Uani d . 1 1
C C2 0.53451(12) 0.09375(11) 0.12252(13) 0.0202(3) Uani d . 1 1
C C3 0.66668(13) -0.01110(11) 0.12946(13) 0.0224(4) Uani d . 1 1
C C4 0.49100(13) -0.05750(11) 0.12589(13) 0.0205(3) Uani d . 1 1
C C5 0.71013(14) 0.13949(12) 0.12604(18) 0.0344(5) Uani d . 1 1
H H5A 0.7050 0.1723 0.0623 0.052 Uiso calc R 1 1
H H5B 0.7767 0.1140 0.1307 0.052 Uiso calc R 1 1
H H5C 0.6994 0.1769 0.1851 0.052 Uiso calc R 1 1
C C6 0.62944(15) -0.16046(12) 0.13966(17) 0.0329(5) Uani d . 1 1
H H6A 0.6593 -0.1777 0.0741 0.049 Uiso calc R 1 1
H H6B 0.5725 -0.1973 0.1554 0.049 Uiso calc R 1 1
H H6C 0.6794 -0.1652 0.1945 0.049 Uiso calc R 1 1
C C7 0.28582(12) 0.00923(11) 0.12190(13) 0.0230(4) Uani d . 1 1
H H7 0.2925 -0.0506 0.1257 0.028 Uiso calc R 1 1
C C8 0.18734(13) 0.04871(11) 0.11802(13) 0.0221(4) Uani d . 1 1
C C9 0.09840(14) 0.00262(12) 0.12149(15) 0.0281(4) Uani d . 1 1
H H9 0.1001 -0.0572 0.1288 0.034 Uiso calc R 1 1
C C10 0.00810(15) 0.04423(13) 0.11423(16) 0.0332(5) Uani d . 1 1
H H10 -0.0525 0.0130 0.1171 0.040 Uiso calc R 1 1
C C11 0.00552(15) 0.13148(13) 0.10267(17) 0.0368(5) Uani d . 1 1
H H11 -0.0564 0.1603 0.0951 0.044 Uiso calc R 1 1
C C12 0.09408(14) 0.17558(12) 0.10235(16) 0.0315(5) Uani d . 1 1
H H12 0.0938 0.2355 0.0967 0.038 Uiso calc R 1 1
Cl Cl1 0.31571(3) 0.28729(3) 0.11637(4) 0.03282(15) Uani d . 1 1
O O90 0.39829(14) 0.33807(11) 0.34015(17) 0.0472(4) Uani d . 1 1
H H901 0.350(2) 0.373(2) 0.359(2) 0.063(8) Uiso d . 1 1
H H902 0.393(2) 0.326(2) 0.279(3) 0.082(12) Uiso d . 1 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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C3 122.87(15)
C2 N1 C5 119.47(15)
C3 N1 C5 117.66(14)
C3 N2 C4 125.03(14)
C3 N2 C6 117.05(14)
C4 N2 C6 117.90(14)
C7 N3 C1 125.19(15)
C2 N4 H741 125.9(15)
C2 N4 H742 119.3(14)
H741 N4 H742 114(2)
C12 N5 C8 123.66(16)
C12 N5 H751 114.9(14)
C8 N5 H751 121.4(14)
N3 C1 C2 115.66(15)
N3 C1 C4 124.67(15)
C2 C1 C4 119.67(15)
N4 C2 N1 118.34(16)
N4 C2 C1 121.85(15)
N1 C2 C1 119.81(15)
O1 C3 N2 122.31(16)
O1 C3 N1 120.87(16)
N2 C3 N1 116.82(15)
O2 C4 N2 119.19(15)
O2 C4 C1 125.12(16)
N2 C4 C1 115.68(15)
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N2 C6 H6A 109.5
N2 C6 H6B 109.5
H6A C6 H6B 109.5
N2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N3 C7 C8 118.36(16)
N3 C7 H7 120.8
C8 C7 H7 120.8
N5 C8 C9 117.73(16)
N5 C8 C7 119.18(16)
C9 C8 C7 123.09(16)
C10 C9 C8 119.75(17)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.20(18)
C9 C10 H10 119.9
C11 C10 H10 119.9
C12 C11 C10 118.85(18)
C12 C11 H11 120.6
C10 C11 H11 120.6
N5 C12 C11 119.75(18)
N5 C12 H12 120.1
C11 C12 H12 120.1
H901 O90 H902 111(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.225(2)
O2 C4 1.225(2)
N1 C2 1.372(2)
N1 C3 1.388(2)
N1 C5 1.474(2)
N2 C3 1.361(2)
N2 C4 1.415(2)
N2 C6 1.470(2)
N3 C7 1.291(2)
N3 C1 1.377(2)
N4 C2 1.321(2)
N4 H741 0.82(2)
N4 H742 0.94(2)
N5 C12 1.338(2)
N5 C8 1.350(2)
N5 H751 0.90(2)
C1 C2 1.407(2)
C1 C4 1.437(2)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.459(2)
C7 H7 0.9500
C8 C9 1.396(2)
C9 C10 1.379(3)
C9 H9 0.9500
C10 C11 1.387(3)
C10 H10 0.9500
C11 C12 1.374(3)
C11 H11 0.9500
C12 H12 0.9500
O90 H901 0.89(3)
O90 H902 0.82(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
N4 H741 O90 4_655 0.82(2) 2.12(2) 2.901(2) 158(2)
N4 H742 Cl1 . 0.94(2) 2.29(2) 3.1565(16) 153(2)
N5 H751 Cl1 . 0.90(2) 2.19(2) 3.0255(16) 155(2)
O90 H901 O1 6_566 0.89(3) 2.01(3) 2.874(2) 164(3)
O90 H902 Cl1 . 0.82(3) 2.43(3) 3.213(2) 159(3)
C5 H5A Cl1 3 0.98 2.83 3.642(2) 141.1
C9 H9 Cl1 7_655 0.95 2.71 3.5912(19) 155.0
C10 H10 O1 1_455 0.95 2.65 3.564(2) 162.8
C12 H12 O2 7_665 0.95 2.37 3.294(2) 164.2
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
C7 N3 C1 C2 -178.39(16)
C7 N3 C1 C4 1.2(3)
C3 N1 C2 N4 -179.57(16)
C5 N1 C2 N4 0.3(3)
C3 N1 C2 C1 0.2(3)
C5 N1 C2 C1 -179.93(17)
N3 C1 C2 N4 -0.9(2)
C4 C1 C2 N4 179.47(17)
N3 C1 C2 N1 179.36(15)
C4 C1 C2 N1 -0.3(2)
C4 N2 C3 O1 -176.43(17)
C6 N2 C3 O1 1.8(3)
C4 N2 C3 N1 3.9(3)
C6 N2 C3 N1 -177.86(16)
C2 N1 C3 O1 178.46(16)
C5 N1 C3 O1 -1.4(3)
C2 N1 C3 N2 -1.9(3)
C5 N1 C3 N2 178.23(16)
C3 N2 C4 O2 176.49(17)
C6 N2 C4 O2 -1.7(3)
C3 N2 C4 C1 -4.0(3)
C6 N2 C4 C1 177.82(16)
N3 C1 C4 O2 1.9(3)
C2 C1 C4 O2 -178.50(17)
N3 C1 C4 N2 -177.63(15)
C2 C1 C4 N2 2.0(2)
C1 N3 C7 C8 -179.65(15)
C12 N5 C8 C9 -2.0(3)
C12 N5 C8 C7 177.56(18)
N3 C7 C8 N5 1.6(3)
N3 C7 C8 C9 -178.81(17)
N5 C8 C9 C10 1.6(3)
C7 C8 C9 C10 -177.98(18)
C8 C9 C10 C11 0.5(3)
C9 C10 C11 C12 -2.3(3)
C8 N5 C12 C11 0.3(3)
C10 C11 C12 N5 1.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656920
