#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/24/7052477.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_7052477
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         '(C7 H5 O2)-, (C5 H8 N3)+, H2O'
_chemical_formula_sum            'C24 H30 N6 O6'
_chemical_formula_weight         498.54
_chemical_name_systematic
;
tropolonate, 2,6-diaminopyridinium, hydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.376(3)
_cell_length_b                   17.697(2)
_cell_length_c                   14.647(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2539.5(10)
_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, 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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.012
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7652
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.12
_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            'pale yellow'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.1081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                4146
_reflns_number_total             7394
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b205705k.txt
_cod_data_source_block           (5)
_cod_original_cell_volume        2539.5(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7052477
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_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
O11 O 0.89360(11) 0.06806(6) 0.18605(8) 0.0642(3) Uani 1 1 d . . .
O21 O 0.70722(10) 0.05159(6) 0.26497(8) 0.0671(3) Uani 1 1 d . . .
C11 C 0.84496(13) 0.12912(8) 0.20720(9) 0.0477(3) Uani 1 1 d . . .
C21 C 0.73894(13) 0.12054(8) 0.25217(9) 0.0501(3) Uani 1 1 d . . .
C31 C 0.67190(18) 0.17946(12) 0.28006(13) 0.0717(5) Uani 1 1 d . . .
C41 C 0.6828(2) 0.25702(13) 0.27469(14) 0.0827(6) Uani 1 1 d . . .
C51 C 0.7654(2) 0.29889(12) 0.23921(14) 0.0807(6) Uani 1 1 d . . .
C61 C 0.8594(2) 0.27190(11) 0.19977(15) 0.0826(5) Uani 1 1 d . . .
C71 C 0.89345(18) 0.19886(10) 0.18641(13) 0.0680(4) Uani 1 1 d . . .
N11 N 0.61888(13) -0.04523(7) 0.10316(8) 0.0511(3) Uani 1 1 d . . .
N21 N 0.78113(14) -0.03354(9) 0.02885(11) 0.0675(4) Uani 1 1 d . . .
N31 N 0.4695(2) -0.04556(11) 0.18900(13) 0.0817(5) Uani 1 1 d . . .
C81 C 0.66828(15) -0.06691(8) 0.03175(10) 0.0518(3) Uani 1 1 d . . .
C91 C 0.59701(17) -0.12279(9) -0.03185(11) 0.0613(4) Uani 1 1 d . . .
C101 C 0.48318(19) -0.15361(10) -0.01918(13) 0.0666(4) Uani 1 1 d . . .
C111 C 0.43433(19) -0.13056(10) 0.05302(13) 0.0691(4) Uani 1 1 d . . .
C121 C 0.50434(16) -0.07444(9) 0.11565(11) 0.0599(4) Uani 1 1 d . . .
O12 O 0.50559(11) -0.09425(6) 0.53348(7) 0.0665(3) Uani 1 1 d . . .
O22 O 0.67362(14) -0.09218(6) 0.70633(9) 0.0913(4) Uani 1 1 d . . .
C12 C 0.54299(14) -0.15850(8) 0.57105(10) 0.0499(3) Uani 1 1 d . . .
C22 C 0.64242(14) -0.15713(8) 0.66962(11) 0.0566(4) Uani 1 1 d . . .
C32 C 0.70162(18) -0.22150(10) 0.72401(15) 0.0721(5) Uani 1 1 d . . .
C42 C 0.6832(2) -0.29743(11) 0.70451(19) 0.0826(6) Uani 1 1 d . . .
C52 C 0.6002(3) -0.33383(12) 0.6254(2) 0.0894(7) Uani 1 1 d . . .
C62 C 0.5123(3) -0.30030(11) 0.54367(17) 0.0873(6) Uani 1 1 d . . .
C72 C 0.4882(2) -0.22462(10) 0.52029(13) 0.0694(4) Uani 1 1 d . . .
N12 N 0.88535(11) -0.04310(6) 0.39367(8) 0.0463(3) Uani 1 1 d . . .
N22 N 0.70226(14) -0.03350(9) 0.44810(12) 0.0673(4) Uani 1 1 d . . .
N32 N 1.05512(15) -0.04375(9) 0.32519(10) 0.0624(3) Uani 1 1 d . . .
C82 C 0.82142(14) -0.06604(8) 0.45682(10) 0.0502(3) Uani 1 1 d . . .
C92 C 0.88438(17) -0.12096(9) 0.52417(11) 0.0603(4) Uani 1 1 d . . .
C102 C 1.00794(17) -0.14943(9) 0.52455(11) 0.0601(4) Uani 1 1 d . . .
C112 C 1.07150(16) -0.12514(8) 0.46131(11) 0.0573(4) Uani 1 1 d . . .
C122 C 1.00750(13) -0.07056(8) 0.39278(10) 0.0481(3) Uani 1 1 d . . .
O1 O 1.12858(15) 0.05382(8) 0.13090(9) 0.0755(4) Uani 1 1 d . . .
O2 O 0.34353(11) -0.05565(7) 0.34797(8) 0.0551(3) Uani 1 1 d . . .
H31 H 0.605(2) 0.1631(12) 0.3065(15) 0.103(7) Uiso 1 1 d . . .
H41 H 0.624(2) 0.2834(12) 0.2989(16) 0.109(7) Uiso 1 1 d . . .
H51 H 0.761(2) 0.3529(14) 0.2437(14) 0.098(6) Uiso 1 1 d . . .
H61 H 0.914(2) 0.3074(12) 0.1773(15) 0.101(7) Uiso 1 1 d . . .
H71 H 0.9593(18) 0.1927(10) 0.1554(13) 0.085(6) Uiso 1 1 d . . .
H11 H 0.6653(16) -0.0115(10) 0.1444(12) 0.065(5) Uiso 1 1 d . . .
H211 H 0.8173(16) 0.0013(9) 0.0745(12) 0.067(5) Uiso 1 1 d . . .
H212 H 0.814(2) -0.0407(11) -0.0216(15) 0.094(6) Uiso 1 1 d . . .
H311 H 0.523(2) -0.0070(13) 0.2245(15) 0.101(7) Uiso 1 1 d . . .
H312 H 0.401(3) -0.0654(12) 0.2006(17) 0.109(8) Uiso 1 1 d . . .
H91 H 0.6267(19) -0.1373(9) -0.0842(14) 0.084(5) Uiso 1 1 d . . .
H101 H 0.4346(17) -0.1917(10) -0.0604(13) 0.072(5) Uiso 1 1 d . . .
H111 H 0.3543(18) -0.1534(9) 0.0610(12) 0.070(5) Uiso 1 1 d . . .
H32 H 0.768(2) -0.2076(11) 0.7841(15) 0.091(6) Uiso 1 1 d . . .
H42 H 0.740(2) -0.3294(13) 0.7581(14) 0.101(6) Uiso 1 1 d . . .
H52 H 0.598(2) -0.3824(13) 0.6295(15) 0.104(7) Uiso 1 1 d . . .
H62 H 0.454(2) -0.3304(13) 0.4939(16) 0.104(7) Uiso 1 1 d . . .
H72 H 0.4212(18) -0.2150(9) 0.4564(14) 0.075(5) Uiso 1 1 d . . .
H12 H 0.8415(15) -0.0095(9) 0.3482(11) 0.057(4) Uiso 1 1 d . . .
H221 H 0.6776(17) 0.0029(10) 0.4113(12) 0.064(5) Uiso 1 1 d . . .
H222 H 0.6543(19) -0.0481(10) 0.4852(13) 0.078(6) Uiso 1 1 d . . .
H321 H 1.0090(17) -0.0071(10) 0.2859(12) 0.074(5) Uiso 1 1 d . . .
H322 H 1.140(2) -0.0538(9) 0.3263(12) 0.072(5) Uiso 1 1 d . . .
H92 H 0.8409(19) -0.1362(10) 0.5725(14) 0.086(6) Uiso 1 1 d . . .
H102 H 1.0523(18) -0.1888(10) 0.5712(13) 0.081(5) Uiso 1 1 d . . .
H112 H 1.1553(18) -0.1453(9) 0.4591(12) 0.073(5) Uiso 1 1 d . . .
H100 H 1.193(2) 0.0684(12) 0.1827(18) 0.098(7) Uiso 1 1 d . . .
H200 H 1.057(2) 0.0641(12) 0.1410(16) 0.099(7) Uiso 1 1 d . . .
H300 H 0.391(2) -0.0696(11) 0.4060(15) 0.088(6) Uiso 1 1 d . . .
H400 H 0.3551(18) -0.0071(12) 0.3469(13) 0.079(6) 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
O11 C11 C71 119.63(13) . . ?
O11 C11 C21 115.98(12) . . ?
C71 C11 C21 124.39(13) . . ?
O21 C21 C31 119.35(14) . . ?
O21 C21 C11 115.32(12) . . ?
C31 C21 C11 125.32(15) . . ?
C41 C31 C21 132.19(18) . . ?
C41 C31 H31 114.4(13) . . ?
C21 C31 H31 113.4(13) . . ?
C51 C41 C31 129.57(18) . . ?
C51 C41 H41 116.7(14) . . ?
C31 C41 H41 113.7(14) . . ?
C41 C51 C61 126.60(19) . . ?
C41 C51 H51 117.7(12) . . ?
C61 C51 H51 115.6(12) . . ?
C71 C61 C51 129.8(2) . . ?
C71 C61 H61 110.9(12) . . ?
C51 C61 H61 119.3(12) . . ?
C61 C71 C11 132.10(17) . . ?
C61 C71 H71 116.1(11) . . ?
C11 C71 H71 111.8(11) . . ?
C81 N11 C121 124.16(14) . . ?
C81 N11 H11 117.6(11) . . ?
C121 N11 H11 118.2(11) . . ?
C81 N21 H211 116.1(10) . . ?
C81 N21 H212 122.0(13) . . ?
H211 N21 H212 121.3(16) . . ?
C121 N31 H311 117.3(13) . . ?
C121 N31 H312 117.5(16) . . ?
H311 N31 H312 125(2) . . ?
N21 C81 N11 117.32(14) . . ?
N21 C81 C91 125.14(14) . . ?
N11 C81 C91 117.54(14) . . ?
C101 C91 C81 118.97(15) . . ?
C101 C91 H91 121.7(11) . . ?
C81 C91 H91 119.3(11) . . ?
C91 C101 C111 122.61(17) . . ?
C91 C101 H101 120.4(10) . . ?
C111 C101 H101 117.0(10) . . ?
C101 C111 C121 118.43(17) . . ?
C101 C111 H111 121.2(10) . . ?
C121 C111 H111 120.4(10) . . ?
N31 C121 N11 116.09(17) . . ?
N31 C121 C111 125.64(17) . . ?
N11 C121 C111 118.27(15) . . ?
O12 C12 C72 120.38(15) . . ?
O12 C12 C22 115.25(13) . . ?
C72 C12 C22 124.35(14) . . ?
O22 C22 C32 119.42(15) . . ?
O22 C22 C12 115.48(13) . . ?
C32 C22 C12 125.10(15) . . ?
C42 C32 C22 131.91(19) . . ?
C42 C32 H32 116.9(12) . . ?
C22 C32 H32 111.1(12) . . ?
C52 C42 C32 130.3(2) . . ?
C52 C42 H42 116.8(13) . . ?
C32 C42 H42 112.8(13) . . ?
C42 C52 C62 126.15(19) . . ?
C42 C52 H52 115.8(15) . . ?
C62 C52 H52 117.8(15) . . ?
C52 C62 C72 130.2(2) . . ?
C52 C62 H62 120.1(13) . . ?
C72 C62 H62 109.6(14) . . ?
C62 C72 C12 131.86(19) . . ?
C62 C72 H72 114.8(10) . . ?
C12 C72 H72 113.4(10) . . ?
C122 N12 C82 124.19(12) . . ?
C122 N12 H12 118.4(9) . . ?
C82 N12 H12 117.4(9) . . ?
C82 N22 H221 118.6(12) . . ?
C82 N22 H222 120.4(12) . . ?
H221 N22 H222 120.7(17) . . ?
C122 N32 H321 119.1(11) . . ?
C122 N32 H322 121.4(11) . . ?
H321 N32 H322 118.1(15) . . ?
N22 C82 N12 116.71(14) . . ?
N22 C82 C92 125.23(15) . . ?
N12 C82 C92 118.06(13) . . ?
C102 C92 C82 118.68(15) . . ?
C102 C92 H92 122.6(11) . . ?
C82 C92 H92 118.6(11) . . ?
C112 C102 C92 122.50(15) . . ?
C112 C102 H102 118.3(10) . . ?
C92 C102 H102 119.2(10) . . ?
C102 C112 C122 118.87(14) . . ?
C102 C112 H112 123.7(10) . . ?
C122 C112 H112 117.4(10) . . ?
N32 C122 N12 117.05(13) . . ?
N32 C122 C112 125.25(14) . . ?
N12 C122 C112 117.69(13) . . ?
H100 O1 H200 105(2) . . ?
H300 O2 H400 105.2(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
O11 C11 1.2734(16) . ?
O21 C21 1.2934(17) . ?
C11 C71 1.404(2) . ?
C11 C21 1.4644(19) . ?
C21 C31 1.387(2) . ?
C31 C41 1.382(3) . ?
C31 H31 0.94(2) . ?
C41 C51 1.359(3) . ?
C41 H41 0.93(2) . ?
C51 C61 1.373(3) . ?
C51 H51 0.96(2) . ?
C61 C71 1.371(3) . ?
C61 H61 0.97(2) . ?
C71 H71 0.943(18) . ?
N11 C81 1.3627(18) . ?
N11 C121 1.363(2) . ?
N11 H11 0.872(17) . ?
N21 C81 1.324(2) . ?
N21 H211 0.897(17) . ?
N21 H212 0.92(2) . ?
N31 C121 1.343(2) . ?
N31 H311 0.93(2) . ?
N31 H312 0.86(2) . ?
C81 C91 1.392(2) . ?
C91 C101 1.368(3) . ?
C91 H91 0.952(19) . ?
C101 C111 1.377(3) . ?
C101 H101 0.934(18) . ?
C111 C121 1.384(2) . ?
C111 H111 0.964(17) . ?
O12 C12 1.2670(17) . ?
O22 C22 1.2651(18) . ?
C12 C72 1.402(2) . ?
C12 C22 1.472(2) . ?
C22 C32 1.410(2) . ?
C32 C42 1.374(3) . ?
C32 H32 0.95(2) . ?
C42 C52 1.357(3) . ?
C42 H42 0.99(2) . ?
C52 C62 1.378(3) . ?
C52 H52 0.86(2) . ?
C62 C72 1.385(3) . ?
C62 H62 0.94(2) . ?
C72 H72 0.979(18) . ?
N12 C122 1.3615(18) . ?
N12 C82 1.3655(18) . ?
N12 H12 0.897(16) . ?
N22 C82 1.331(2) . ?
N22 H221 0.824(17) . ?
N22 H222 0.89(2) . ?
N32 C122 1.3310(19) . ?
N32 H321 0.894(18) . ?
N32 H322 0.893(19) . ?
C82 C92 1.386(2) . ?
C92 C102 1.376(2) . ?
C92 H92 0.994(19) . ?
C102 C112 1.371(2) . ?
C102 H102 0.978(18) . ?
C112 C122 1.394(2) . ?
C112 H112 0.951(17) . ?
O1 H100 0.87(3) . ?
O1 H200 0.83(2) . ?
O2 H300 0.87(2) . ?
O2 H400 0.87(2) . ?
