#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/09/7050967.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7050967
loop_
_publ_author_name
'Bertolasi, Valerio'
'Pretto, Loretta'
'Gilli, Paola'
'Ferretti, Valeria'
'Gilli, Gastone'
_publ_section_title
;
 Hydrogen-bonded supramolecular structures in co-crystals of ??- or
 ??-diketone enols with 2,6-diaminopyridine or 2,4-diaminopyrimidine
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1559
_journal_paper_doi               10.1039/b205705k
_journal_volume                  26
_journal_year                    2002
_chemical_formula_moiety         '(C5 H5 O2)-, (C5 N3 H8)+, H2 O'
_chemical_formula_sum            'C10 H15 N3 O3'
_chemical_formula_weight         225.25
_chemical_name_systematic
; 
1,3-cyclopentanedionate, 2,6-diaminopyridinium, hydrate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.56(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.394(2)
_cell_length_b                   19.603(2)
_cell_length_c                   8.107(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1171.3(4)
_computing_cell_refinement       'CAD4 Enraf-Nonius, 1984'
_computing_data_collection       'CAD4 Enraf-Nonius, 1984'
_computing_data_reduction        'MolEN (Fair, Enraf-Nonius, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994) '
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3631
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0481
_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)+(0.0710P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                2013
_reflns_number_total             3413
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b205705k.txt
_cod_data_source_block           (1)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7050967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88015(15) 0.11221(5) 0.73551(13) 0.0600(3) Uani 1 1 d . . .
O2 O 0.74121(16) 0.00156(5) 0.22875(13) 0.0636(3) Uani 1 1 d . . .
C1 C 0.82575(17) 0.06853(6) 0.62729(17) 0.0449(3) Uani 1 1 d . . .
C2 C 0.81584(19) 0.07522(7) 0.45774(18) 0.0466(3) Uani 1 1 d . . .
C3 C 0.75914(17) 0.01434(7) 0.38043(17) 0.0454(3) Uani 1 1 d . . .
C4 C 0.72039(19) -0.03778(7) 0.51026(18) 0.0466(3) Uani 1 1 d . . .
C5 C 0.7635(2) -0.00173(7) 0.67429(19) 0.0493(3) Uani 1 1 d . . .
N1 N 1.18602(16) 0.19417(5) 0.76709(14) 0.0471(3) Uani 1 1 d . . .
N2 N 1.4124(2) 0.12350(7) 0.87868(19) 0.0640(4) Uani 1 1 d . . .
N3 N 0.9392(2) 0.25563(8) 0.6570(2) 0.0660(4) Uani 1 1 d . . .
C6 C 1.3597(2) 0.18594(7) 0.83145(18) 0.0502(3) Uani 1 1 d . . .
C7 C 1.4700(3) 0.24370(8) 0.8445(2) 0.0630(4) Uani 1 1 d . . .
C8 C 1.3996(3) 0.30512(8) 0.7923(2) 0.0679(5) Uani 1 1 d . . .
C9 C 1.2239(2) 0.31229(8) 0.7277(2) 0.0613(4) Uani 1 1 d . . .
C10 C 1.1133(2) 0.25539(7) 0.71579(17) 0.0488(3) Uani 1 1 d . . .
O3 O 0.78588(18) 0.11523(6) 1.04722(15) 0.0638(3) Uani 1 1 d . . .
H2 H 0.848(2) 0.1147(8) 0.4044(19) 0.053(4) Uiso 1 1 d . . .
H41 H 0.799(2) -0.0779(8) 0.4950(18) 0.053(4) Uiso 1 1 d . . .
H42 H 0.594(2) -0.0544(8) 0.4894(17) 0.054(4) Uiso 1 1 d . . .
H51 H 0.865(2) -0.0236(8) 0.7413(18) 0.053(4) Uiso 1 1 d . . .
H52 H 0.656(2) 0.0010(8) 0.742(2) 0.063(4) Uiso 1 1 d . . .
H1 H 1.108(2) 0.1584(8) 0.7637(19) 0.057(4) Uiso 1 1 d . . .
H21 H 1.340(3) 0.0818(11) 0.849(3) 0.094(6) Uiso 1 1 d . . .
H22 H 1.522(3) 0.1161(9) 0.931(2) 0.075(6) Uiso 1 1 d . . .
H31 H 0.879(3) 0.2981(10) 0.627(2) 0.081(6) Uiso 1 1 d . . .
H32 H 0.877(2) 0.2180(10) 0.664(2) 0.070(5) Uiso 1 1 d . . .
H7 H 1.588(3) 0.2390(9) 0.883(2) 0.072(5) Uiso 1 1 d . . .
H8 H 1.477(3) 0.3453(10) 0.800(2) 0.087(6) Uiso 1 1 d . . .
H9 H 1.169(2) 0.3563(9) 0.686(2) 0.071(5) Uiso 1 1 d . . .
H301 H 0.779(3) 0.0723(11) 1.106(2) 0.082(6) Uiso 1 1 d . . .
H302 H 0.829(3) 0.1057(10) 0.949(3) 0.092(7) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 127.96(12) . . ?
O1 C1 C5 121.82(13) . . ?
C2 C1 C5 110.21(12) . . ?
C1 C2 C3 110.91(12) . . ?
C1 C2 H2 123.3(9) . . ?
C3 C2 H2 125.7(9) . . ?
O2 C3 C2 128.06(13) . . ?
O2 C3 C4 122.55(12) . . ?
C2 C3 C4 109.39(12) . . ?
C3 C4 C5 104.92(11) . . ?
C3 C4 H41 107.6(9) . . ?
C5 C4 H41 113.2(9) . . ?
C3 C4 H42 109.4(9) . . ?
C5 C4 H42 115.6(8) . . ?
H41 C4 H42 105.9(12) . . ?
C1 C5 C4 104.50(11) . . ?
C1 C5 H51 107.5(9) . . ?
C4 C5 H51 112.1(9) . . ?
C1 C5 H52 111.1(9) . . ?
C4 C5 H52 112.8(9) . . ?
H51 C5 H52 108.6(13) . . ?
C6 N1 C10 123.98(12) . . ?
C6 N1 H1 120.1(10) . . ?
C10 N1 H1 115.8(10) . . ?
C6 N2 H21 123.2(12) . . ?
C6 N2 H22 121.2(12) . . ?
H21 N2 H22 115.4(17) . . ?
C10 N3 H31 120.1(11) . . ?
C10 N3 H32 118.3(12) . . ?
H31 N3 H32 120.7(17) . . ?
N2 C6 N1 117.80(13) . . ?
N2 C6 C7 124.64(15) . . ?
N1 C6 C7 117.56(14) . . ?
C8 C7 C6 119.09(17) . . ?
C8 C7 H7 121.9(12) . . ?
C6 C7 H7 119.0(12) . . ?
C7 C8 C9 122.41(15) . . ?
C7 C8 H8 119.1(12) . . ?
C9 C8 H8 118.5(12) . . ?
C8 C9 C10 118.83(15) . . ?
C8 C9 H9 124.6(11) . . ?
C10 C9 H9 116.6(11) . . ?
N3 C10 N1 117.14(13) . . ?
N3 C10 C9 124.74(14) . . ?
N1 C10 C9 118.13(15) . . ?
H301 O3 H302 107.0(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2683(16) . ?
O2 C3 1.2516(17) . ?
C1 C2 1.377(2) . ?
C1 C5 1.5108(18) . ?
C2 C3 1.3967(19) . ?
C2 H2 0.928(16) . ?
C3 C4 1.5105(19) . ?
C4 C5 1.517(2) . ?
C4 H41 0.992(16) . ?
C4 H42 0.990(15) . ?
C5 H51 0.988(15) . ?
C5 H52 1.004(18) . ?
N1 C6 1.3567(19) . ?
N1 C10 1.3663(17) . ?
N1 H1 0.907(17) . ?
N2 C6 1.3317(19) . ?
N2 H21 0.99(2) . ?
N2 H22 0.90(2) . ?
N3 C10 1.337(2) . ?
N3 H31 0.97(2) . ?
N3 H32 0.874(19) . ?
C6 C7 1.395(2) . ?
C7 C8 1.365(3) . ?
C7 H7 0.906(19) . ?
C8 C9 1.369(3) . ?
C8 H8 0.97(2) . ?
C9 C10 1.382(2) . ?
C9 H9 1.003(18) . ?
O3 H301 0.97(2) . ?
O3 H302 0.90(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652851
