#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:26:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179579 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504477.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_4504477
loop_
_publ_author_name
'Yigit, Mehmet V.'
'Biyikli, Kasim'
'Moulton, Brian'
'MacDonald, John C.'
_publ_section_title
;
 Bis(imidazolium 2,4,6-tricarboxypyridine) Metal(II) Complexes: 
 Molecular Building Blocks that Generate Isomorphous Hydrogen-Bonded
 Frameworks
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              63
_journal_paper_doi               10.1021/cg050084t
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C22 H22 Co N6 O15'
_chemical_formula_weight         667.37
_chemical_melting_point          'decomposes above 220 degrees C'
_chemical_name_systematic
;
 bis(imidazolium 2,4,6-tricarboxypyridine) cobalt(II) trihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 112.172(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.172(3)
_cell_length_b                   18.456(4)
_cell_length_c                   9.900(2)
_cell_measurement_temperature    200(2)
_cell_volume                     2736.4(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8552
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0785P)²+3.8291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                2790
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050084tsi20050909_105434.cif
_cod_data_source_block           co_final
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4504477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Co1 Co 0.5000 0.70789(2) 0.7500 0.02916(17) Uani 1 2 d S
N1 N 0.39009(14) 0.70726(10) 0.8010(2) 0.0278(4) Uani 1 1 d .
O1 O 0.41727(13) 0.78912(10) 0.6095(2) 0.0413(5) Uani 1 1 d .
O2 O 0.28415(14) 0.84282(11) 0.5497(2) 0.0454(5) Uani 1 1 d .
O3 O 0.53079(12) 0.62944(10) 0.9259(2) 0.0395(4) Uani 1 1 d .
O4 O 0.47416(13) 0.57932(12) 1.0786(2) 0.0486(5) Uani 1 1 d .
O5 O 0.08356(17) 0.7255(2) 0.7754(4) 0.0856(10) Uani 1 1 d .
H5O H 0.0351 0.7103 0.7715 0.103 Uiso 0.50 1 calc PR
O6 O 0.1374(2) 0.63822(19) 0.9384(4) 0.0955(11) Uani 1 1 d .
H6 H 0.0859 0.6375 0.9348 0.115 Uiso 0.50 1 calc PR
C1 C 0.32166(16) 0.74892(13) 0.7242(3) 0.0293(5) Uani 1 1 d .
C2 C 0.24080(17) 0.74417(14) 0.7415(3) 0.0353(5) Uani 1 1 d .
H2 H 0.1929 0.7734 0.6874 0.042 Uiso 1 1 calc R
C3 C 0.23317(17) 0.69475(15) 0.8415(3) 0.0351(5) Uani 1 1 d .
C4 C 0.30643(17) 0.65349(14) 0.9254(3) 0.0341(5) Uani 1 1 d .
H4 H 0.3029 0.6215 0.9957 0.041 Uiso 1 1 calc R
C5 C 0.38484(16) 0.66134(13) 0.9012(3) 0.0293(5) Uani 1 1 d .
C6 C 0.34190(18) 0.79841(13) 0.6180(3) 0.0330(5) Uani 1 1 d .
C7 C 0.14416(18) 0.68418(18) 0.8529(3) 0.0441(7) Uani 1 1 d .
C8 C 0.47025(16) 0.61932(14) 0.9764(3) 0.0329(5) Uani 1 1 d .
N1I N 0.75773(16) 1.04105(13) 0.6265(3) 0.0433(5) Uani 1 1 d .
H1N H 0.7289 1.0737 0.5646 0.052 Uiso 1 1 calc R
N2I N 0.86343(16) 0.97404(12) 0.7630(3) 0.0392(5) Uani 1 1 d .
H2N H 0.9156 0.9554 0.8058 0.047 Uiso 1 1 calc R
C1I C 0.84363(18) 1.02689(14) 0.6676(3) 0.0379(6) Uani 1 1 d .
H1I H 0.8833 1.0503 0.6346 0.045 Uiso 1 1 calc R
C2I C 0.7219(2) 0.99525(19) 0.6987(4) 0.0525(8) Uani 1 1 d .
H2I H 0.6627 0.9936 0.6902 0.063 Uiso 1 1 calc R
C3I C 0.7883(2) 0.95343(16) 0.7834(3) 0.0465(7) Uani 1 1 d .
H3I H 0.7841 0.9169 0.8451 0.056 Uiso 1 1 calc R
O1W O 0.9949(3) 0.6037(2) 0.0050(6) 0.1294(17) Uani 1 1 d .
O2W O 0.0000 0.4892(4) 0.7500 0.209(5) Uani 1 2 d S
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'
Co Co 0.3494 0.9721 '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
N1 Co1 N1 179.33(11) 2_656 .
N1 Co1 O1 76.90(8) 2_656 2_656
N1 Co1 O1 103.58(8) . 2_656
N1 Co1 O1 103.59(8) 2_656 .
N1 Co1 O1 76.90(8) . .
O1 Co1 O1 90.92(12) 2_656 .
N1 Co1 O3 75.72(7) 2_656 2_656
N1 Co1 O3 103.82(7) . 2_656
O1 Co1 O3 152.47(7) 2_656 2_656
O1 Co1 O3 92.75(8) . 2_656
N1 Co1 O3 103.82(7) 2_656 .
N1 Co1 O3 75.72(7) . .
O1 Co1 O3 92.75(8) 2_656 .
O1 Co1 O3 152.47(7) . .
O3 Co1 O3 96.43(11) 2_656 .
C1 N1 C5 121.5(2) . .
C1 N1 Co1 118.40(16) . .
C5 N1 Co1 119.92(16) . .
C6 O1 Co1 115.72(16) . .
C8 O3 Co1 115.83(15) . .
N1 C1 C2 121.0(2) . .
N1 C1 C6 113.2(2) . .
C2 C1 C6 125.7(2) . .
C1 C2 C3 118.2(2) . .
C2 C3 C4 120.1(2) . .
C2 C3 C7 119.1(2) . .
C4 C3 C7 120.7(2) . .
C5 C4 C3 118.0(2) . .
N1 C5 C4 121.0(2) . .
N1 C5 C8 112.9(2) . .
C4 C5 C8 126.0(2) . .
O2 C6 O1 127.0(2) . .
O2 C6 C1 117.5(2) . .
O1 C6 C1 115.4(2) . .
O6 C7 O5 126.1(3) . .
O6 C7 C3 118.6(3) . .
O5 C7 C3 115.3(3) . .
O4 C8 O3 127.0(2) . .
O4 C8 C5 117.7(2) . .
O3 C8 C5 115.3(2) . .
C1I N1I C2I 108.7(2) . .
C1I N2I C3I 109.1(2) . .
N2I C1I N1I 108.2(2) . .
C3I C2I N1I 106.7(3) . .
C2I C3I N2I 107.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 N1 2.023(2) 2_656
Co1 N1 2.023(2) .
Co1 O1 2.1372(19) 2_656
Co1 O1 2.1373(19) .
Co1 O3 2.1729(19) 2_656
Co1 O3 2.1730(19) .
N1 C1 1.326(3) .
N1 C5 1.332(3) .
O1 C6 1.265(3) .
O2 C6 1.235(3) .
O3 C8 1.270(3) .
O4 C8 1.235(3) .
O5 C7 1.251(4) .
O6 C7 1.232(4) .
C1 C2 1.384(3) .
C1 C6 1.519(3) .
C2 C3 1.386(4) .
C3 C4 1.389(4) .
C3 C7 1.499(3) .
C4 C5 1.384(3) .
C5 C8 1.512(3) .
N1I C1I 1.318(4) .
N1I C2I 1.368(4) .
N2I C1I 1.310(3) .
N2I C3I 1.358(4) .
C2I C3I 1.332(5) .
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
_geom_torsion_site_symmetry_1
N1 Co1 N1 C1 -131.48(17) 2_656
O1 Co1 N1 C1 92.46(19) 2_656
O1 Co1 N1 C1 4.71(17) .
O3 Co1 N1 C1 -84.92(18) 2_656
O3 Co1 N1 C1 -178.15(19) .
N1 Co1 N1 C5 43.0(2) 2_656
O1 Co1 N1 C5 -93.04(19) 2_656
O1 Co1 N1 C5 179.2(2) .
O3 Co1 N1 C5 89.59(19) 2_656
O3 Co1 N1 C5 -3.65(18) .
N1 Co1 O1 C6 178.01(19) 2_656
N1 Co1 O1 C6 -1.52(19) .
O1 Co1 O1 C6 -105.3(2) 2_656
O3 Co1 O1 C6 102.0(2) 2_656
O3 Co1 O1 C6 -7.5(3) .
N1 Co1 O3 C8 -179.16(19) 2_656
N1 Co1 O3 C8 0.34(18) .
O1 Co1 O3 C8 103.66(19) 2_656
O1 Co1 O3 C8 6.4(3) .
O3 Co1 O3 C8 -102.3(2) 2_656
C5 N1 C1 C2 -2.6(4) .
Co1 N1 C1 C2 171.85(19) .
C5 N1 C1 C6 178.9(2) .
Co1 N1 C1 C6 -6.7(3) .
N1 C1 C2 C3 0.2(4) .
C6 C1 C2 C3 178.6(2) .
C1 C2 C3 C4 2.4(4) .
C1 C2 C3 C7 -174.9(2) .
C2 C3 C4 C5 -2.6(4) .
C7 C3 C4 C5 174.6(2) .
C1 N1 C5 C4 2.3(4) .
Co1 N1 C5 C4 -171.99(19) .
C1 N1 C5 C8 -179.8(2) .
Co1 N1 C5 C8 5.9(3) .
C3 C4 C5 N1 0.3(4) .
C3 C4 C5 C8 -177.3(2) .
Co1 O1 C6 O2 178.7(2) .
Co1 O1 C6 C1 -1.4(3) .
N1 C1 C6 O2 -174.8(2) .
C2 C1 C6 O2 6.7(4) .
N1 C1 C6 O1 5.2(3) .
C2 C1 C6 O1 -173.3(2) .
C2 C3 C7 O6 177.4(3) .
C4 C3 C7 O6 0.1(5) .
C2 C3 C7 O5 -4.6(4) .
C4 C3 C7 O5 178.2(3) .
Co1 O3 C8 O4 -177.6(2) .
Co1 O3 C8 C5 2.5(3) .
N1 C5 C8 O4 174.7(2) .
C4 C5 C8 O4 -7.5(4) .
N1 C5 C8 O3 -5.4(3) .
C4 C5 C8 O3 172.4(2) .
C3I N2I C1I N1I 0.3(3) .
C2I N1I C1I N2I -0.1(3) .
C1I N1I C2I C3I -0.1(4) .
N1I C2I C3I N2I 0.3(4) .
C1I N2I C3I C2I -0.3(4) .
