#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017759.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_2017759
loop_
_publ_author_name
'Sridhar, Balasubramanian'
'Ravikumar, Krishnan'
_publ_section_title
;
 Supramolecular hydrogen-bonded networks in cytosinium nicotinate
 monohydrate and cytosinium isonicotinate cytosine dihydrate
;
_journal_coeditor_code           SF3134
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o414
_journal_page_last               o417
_journal_paper_doi               10.1107/S0108270110026430
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'C4 H6 N3 O + , C6 H4 N O2 - , C4 H5 N3 O , 2H2 O'
_chemical_formula_moiety
'C4 H6 N3 O + , C6 H4 N O2 - , C4 H5 N3 O , 2H2 O'
_chemical_formula_sum            'C14 H19 N7 O6'
_chemical_formula_weight         381.36
_chemical_name_common            'cytosinium isonicotinate cytosine dihydrate'
_chemical_name_systematic
;
4-amino-2-oxo-2,3-dihydropyrimidin-1-ium
isonicotinate--4-aminopyrimidin-2(1H)-one--water (1/1/2)
;
_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                99.831(2)
_cell_angle_beta                 92.928(2)
_cell_angle_gamma                107.862(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1852(8)
_cell_length_b                   7.3627(8)
_cell_length_c                   17.7387(18)
_cell_measurement_reflns_used    4610
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.34
_cell_volume                     874.70(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8483
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0409
_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)+(0.0807P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                2751
_reflns_number_total             3083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3134.cif
_cod_data_source_block           II
_cod_database_code               2017759
_cod_database_fobs_code          2017759
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
C C2A 0.6069(2) 1.2108(2) 0.38576(8) 0.0374(3) Uani d . 1 . .
C C4A 0.6144(2) 0.8963(2) 0.38975(8) 0.0368(3) Uani d . 1 . .
C C5A 0.5315(2) 0.8287(2) 0.31191(9) 0.0436(4) Uani d . 1 . .
H H5A 0.5058 0.6997 0.2877 0.052 Uiso calc R 1 . .
C C6A 0.4918(2) 0.9582(2) 0.27464(9) 0.0455(4) Uani d . 1 . .
H H6A 0.4379 0.9190 0.2234 0.055 Uiso calc R 1 . .
N N1A 0.52901(19) 1.14623(18) 0.31048(7) 0.0430(3) Uani d . 1 . .
H H1A 0.488(3) 1.227(3) 0.2820(12) 0.062(5) Uiso d . 1 . .
N N3A 0.65268(18) 1.08314(16) 0.42440(7) 0.0381(3) Uani d . 1 . .
N N7A 0.6549(2) 0.7774(2) 0.43129(9) 0.0464(3) Uani d . 1 . .
H H7A 0.630(3) 0.654(3) 0.4127(11) 0.056(5) Uiso d . 1 . .
H H8A 0.710(3) 0.829(3) 0.4807(12) 0.056(5) Uiso d . 1 . .
O O8A 0.63483(17) 1.38231(15) 0.41713(6) 0.0506(3) Uani d . 1 . .
C C2B 0.8936(2) 1.1051(2) 0.61533(8) 0.0366(3) Uani d . 1 . .
C C4B 0.8905(2) 1.4256(2) 0.60700(8) 0.0374(3) Uani d . 1 . .
C C5B 0.9878(2) 1.4965(2) 0.68276(9) 0.0445(4) Uani d . 1 . .
H H5B 1.0222 1.6275 0.7055 0.053 Uiso calc R 1 . .
C C6B 1.0286(2) 1.3683(2) 0.72048(9) 0.0449(4) Uani d . 1 . .
H H6B 1.0910 1.4117 0.7705 0.054 Uiso calc R 1 . .
N N1B 0.98202(19) 1.17733(18) 0.68825(7) 0.0413(3) Uani d . 1 . .
H H1B 1.001(3) 1.087(3) 0.7188(12) 0.073(6) Uiso d . 1 . .
N N3B 0.85146(18) 1.23564(16) 0.57567(7) 0.0371(3) Uani d . 1 . .
H H3B 0.779(3) 1.186(3) 0.5237(13) 0.075(6) Uiso d . 1 . .
N N7B 0.8358(2) 1.5361(2) 0.56600(8) 0.0487(4) Uani d . 1 . .
H H7B 0.853(3) 1.661(3) 0.5842(12) 0.065(6) Uiso d . 1 . .
H H8B 0.768(3) 1.478(3) 0.5185(12) 0.056(5) Uiso d . 1 . .
O O8B 0.85081(17) 0.93212(14) 0.58537(6) 0.0485(3) Uani d . 1 . .
C C11 1.1259(2) 1.0564(2) 0.84675(9) 0.0430(4) Uani d . 1 . .
C C12 1.1685(2) 0.9584(2) 0.91075(8) 0.0422(4) Uani d . 1 . .
C C13 1.2473(2) 1.0642(2) 0.98333(9) 0.0467(4) Uani d . 1 . .
H H13 1.2762 1.1987 0.9942 0.056 Uiso calc R 1 . .
C C14 1.2823(3) 0.9665(3) 1.03958(10) 0.0543(4) Uani d . 1 . .
H H14 1.3330 1.0389 1.0887 0.065 Uiso calc R 1 . .
C C16 1.1728(3) 0.6753(3) 0.95761(11) 0.0685(5) Uani d . 1 . .
H H16 1.1482 0.5414 0.9478 0.082 Uiso calc R 1 . .
C C17 1.1297(3) 0.7603(3) 0.89875(10) 0.0614(5) Uani d . 1 . .
H H17 1.0742 0.6837 0.8508 0.074 Uiso calc R 1 . .
N N15 1.2479(2) 0.7755(2) 1.02790(9) 0.0603(4) Uani d . 1 . .
O O9 1.02491(18) 0.94678(16) 0.78613(6) 0.0559(3) Uani d . 1 . .
O O10 1.19248(19) 1.23543(16) 0.85658(7) 0.0599(4) Uani d . 1 . .
O O1W 0.3493(2) 1.3221(2) 0.21982(8) 0.0640(4) Uani d . 1 . .
H H1W 0.231(4) 1.243(4) 0.2141(13) 0.089(8) Uiso d . 1 . .
H H2W 0.358(3) 1.399(4) 0.1864(14) 0.086(7) Uiso d . 1 . .
O O2W 0.4076(3) 1.5630(3) 0.11872(11) 0.0930(6) Uani d . 1 . .
H H3W 0.525(4) 1.618(4) 0.1211(14) 0.090(8) Uiso d . 1 . .
H H4W 0.350(4) 1.620(4) 0.0942(16) 0.103(9) 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
O8A C2A N3A . . 121.62(13) ?
O8A C2A N1A . . 120.01(12) ?
N3A C2A N1A . . 118.36(12) ?
N7A C4A N3A . . 117.50(13) ?
N7A C4A C5A . . 121.21(13) ?
N3A C4A C5A . . 121.28(13) ?
C6A C5A C4A . . 117.20(13) ?
C6A C5A H5A . . 121.4 ?
C4A C5A H5A . . 121.4 ?
C5A C6A N1A . . 121.03(14) ?
C5A C6A H6A . . 119.5 ?
N1A C6A H6A . . 119.5 ?
C6A N1A C2A . . 121.74(13) ?
C6A N1A H1A . . 116.5(12) ?
C2A N1A H1A . . 121.6(12) ?
C4A N3A C2A . . 120.33(12) y
C4A N7A H7A . . 122.1(12) ?
C4A N7A H8A . . 117.7(11) ?
H7A N7A H8A . . 120.1(17) ?
O8B C2B N1B . . 122.52(13) ?
O8B C2B N3B . . 120.90(13) ?
N1B C2B N3B . . 116.57(12) ?
N7B C4B N3B . . 118.39(13) ?
N7B C4B C5B . . 122.91(14) ?
N3B C4B C5B . . 118.69(13) ?
C6B C5B C4B . . 117.66(14) ?
C6B C5B H5B . . 121.2 ?
C4B C5B H5B . . 121.2 ?
C5B C6B N1B . . 122.17(14) ?
C5B C6B H6B . . 118.9 ?
N1B C6B H6B . . 118.9 ?
C6B N1B C2B . . 121.89(12) ?
C6B N1B H1B . . 119.8(12) ?
C2B N1B H1B . . 118.0(13) ?
C4B N3B C2B . . 122.94(12) y
C4B N3B H3B . . 118.4(12) ?
C2B N3B H3B . . 118.4(12) ?
C4B N7B H7B . . 122.3(13) ?
C4B N7B H8B . . 117.5(12) ?
H7B N7B H8B . . 120.0(18) ?
O10 C11 O9 . . 124.69(14) y
O10 C11 C12 . . 118.49(13) y
O9 C11 C12 . . 116.82(13) y
C17 C12 C13 . . 117.54(15) ?
C17 C12 C11 . . 121.24(14) ?
C13 C12 C11 . . 121.22(14) ?
C12 C13 C14 . . 118.62(16) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
N15 C14 C13 . . 124.02(16) ?
N15 C14 H14 . . 118.0 ?
C13 C14 H14 . . 118.0 ?
N15 C16 C17 . . 123.02(18) ?
N15 C16 H16 . . 118.5 ?
C17 C16 H16 . . 118.5 ?
C16 C17 C12 . . 120.02(17) ?
C16 C17 H17 . . 120.0 ?
C12 C17 H17 . . 120.0 ?
C14 N15 C16 . . 116.75(15) ?
H1W O1W H2W . . 108(2) ?
H3W O2W H4W . . 108(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
C2A O8A . 1.2399(17) ?
C2A N3A . 1.3596(18) ?
C2A N1A . 1.3661(19) ?
C4A N7A . 1.3223(19) ?
C4A N3A . 1.3444(18) ?
C4A C5A . 1.417(2) ?
C5A C6A . 1.338(2) ?
C5A H5A . 0.9300 ?
C6A N1A . 1.359(2) ?
C6A H6A . 0.9300 ?
N1A H1A . 0.94(2) ?
N7A H7A . 0.87(2) ?
N7A H8A . 0.91(2) ?
C2B O8B . 1.2292(17) ?
C2B N1B . 1.3539(19) ?
C2B N3B . 1.3778(18) ?
C4B N7B . 1.3092(19) ?
C4B N3B . 1.3498(18) ?
C4B C5B . 1.417(2) ?
C5B C6B . 1.338(2) ?
C5B H5B . 0.9300 ?
C6B N1B . 1.3536(19) ?
C6B H6B . 0.9300 ?
N1B H1B . 0.96(2) ?
N3B H3B . 0.99(2) ?
N7B H7B . 0.89(2) ?
N7B H8B . 0.92(2) ?
C11 O10 . 1.2340(18) y
C11 O9 . 1.2645(18) y
C11 C12 . 1.511(2) ?
C12 C17 . 1.374(2) ?
C12 C13 . 1.377(2) ?
C13 C14 . 1.381(2) ?
C13 H13 . 0.9300 ?
C14 N15 . 1.328(2) ?
C14 H14 . 0.9300 ?
C16 N15 . 1.328(3) ?
C16 C17 . 1.373(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
O1W H1W . 0.86(3) ?
O1W H2W . 0.88(3) ?
O2W H3W . 0.81(3) ?
O2W H4W . 0.83(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
N1A H1A O1W . 0.94(2) 1.81(2) 2.730(2) 164(2)
N7A H7A O8A 1_545 0.87(2) 2.02(2) 2.835(2) 154(2)
N7A H8A O8B . 0.91(2) 1.98(2) 2.883(2) 175(2)
N1B H1B O9 . 0.96(2) 1.74(2) 2.695(2) 171(2)
N3B H3B N3A . 0.99(2) 1.86(2) 2.846(2) 176(2)
N7B H7B O8B 1_565 0.89(2) 2.00(2) 2.845(2) 159(2)
N7B H8B O8A . 0.92(2) 1.90(2) 2.816(2) 174(2)
O1W H1W O9 2_676 0.86(3) 1.94(3) 2.792(2) 172(2)
O1W H2W O2W . 0.88(3) 1.82(3) 2.691(2) 173(2)
O2W H3W O10 2_786 0.81(3) 1.96(3) 2.772(2) 171(2)
O2W H4W N15 1_464 0.83(3) 2.03(3) 2.852(2) 171(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
N7A C4A C5A C6A . . . . 178.76(14) ?
N3A C4A C5A C6A . . . . -0.5(2) ?
C4A C5A C6A N1A . . . . -0.3(2) ?
C5A C6A N1A C2A . . . . -0.4(2) ?
O8A C2A N1A C6A . . . . -178.38(14) ?
N3A C2A N1A C6A . . . . 1.9(2) ?
N7A C4A N3A C2A . . . . -177.30(13) ?
C5A C4A N3A C2A . . . . 2.0(2) ?
O8A C2A N3A C4A . . . . 177.65(13) ?
N1A C2A N3A C4A . . . . -2.6(2) ?
N7B C4B C5B C6B . . . . 176.98(15) ?
N3B C4B C5B C6B . . . . -2.8(2) ?
C4B C5B C6B N1B . . . . 0.8(2) ?
C5B C6B N1B C2B . . . . 1.0(2) ?
O8B C2B N1B C6B . . . . 179.91(14) ?
N3B C2B N1B C6B . . . . -0.6(2) ?
N7B C4B N3B C2B . . . . -176.57(13) ?
C5B C4B N3B C2B . . . . 3.2(2) ?
O8B C2B N3B C4B . . . . 177.98(13) ?
N1B C2B N3B C4B . . . . -1.5(2) ?
O10 C11 C12 C17 . . . . -168.25(17) ?
O9 C11 C12 C17 . . . . 11.1(2) ?
O10 C11 C12 C13 . . . . 11.9(2) ?
O9 C11 C12 C13 . . . . -168.74(15) ?
C17 C12 C13 C14 . . . . -0.1(2) ?
C11 C12 C13 C14 . . . . 179.74(14) ?
C12 C13 C14 N15 . . . . 1.2(3) ?
N15 C16 C17 C12 . . . . 1.6(3) ?
C13 C12 C17 C16 . . . . -1.2(3) ?
C11 C12 C17 C16 . . . . 178.95(17) ?
C13 C14 N15 C16 . . . . -0.9(3) ?
C17 C16 N15 C14 . . . . -0.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654255
