#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:26:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179579 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504478.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_4504478
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 N6 Ni O15'
_chemical_formula_weight         667.15
_chemical_melting_point          'decomposes above 220 degrees C'
_chemical_name_systematic
;
 bis(imidazolium 2,4,6-tricarboxypyridine) nickel(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                 111.6090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0967(13)
_cell_length_b                   18.4218(15)
_cell_length_c                   9.8346(8)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.41
_cell_volume                     2711.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SMART'
_computing_publication_material  'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8127
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0465
_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)+(0.0517P)²+6.7629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2674
_reflns_number_total             3062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050084tsi20050909_105453.cif
_cod_data_source_block           ni_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               4504478
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
Ni1 Ni 0.0000 0.20551(2) 0.7500 0.01883(15) Uani 1 2 d S
O1A O 0.07900(12) 0.28583(10) 0.8933(2) 0.0258(4) Uani 1 1 d .
N1A N 0.10774(14) 0.20541(11) 0.6995(2) 0.0197(4) Uani 1 1 d .
O2A O 0.21170(13) 0.34179(11) 0.9522(2) 0.0307(5) Uani 1 1 d .
O3A O -0.03288(12) 0.12738(10) 0.5763(2) 0.0244(4) Uani 1 1 d .
O4A O 0.02380(13) 0.07751(11) 0.4200(2) 0.0319(5) Uani 1 1 d .
O5A O 0.41597(15) 0.22600(17) 0.7234(3) 0.0598(8) Uani 1 1 d .
H5A H 0.4639 0.2168 0.7112 0.072 Uiso 0.50 1 calc PR
C6A C 0.11341(16) 0.15961(13) 0.5987(3) 0.0211(5) Uani 1 1 d .
O6A O 0.36377(18) 0.13648(17) 0.5629(4) 0.0730(10) Uani 1 1 d .
H6A H 0.4167 0.1360 0.5664 0.088 Uiso 0.50 1 calc PR
C5A C 0.19223(17) 0.15220(14) 0.5731(3) 0.0238(5) Uani 1 1 d .
H5A H 0.1962 0.1198 0.5006 0.029 Uiso 1 1 calc R
C3A C 0.25733(17) 0.24367(15) 0.7583(3) 0.0244(5) Uani 1 1 d .
H3A H 0.3060 0.2739 0.8130 0.029 Uiso 1 1 calc R
C1A C 0.15444(17) 0.29630(14) 0.8836(3) 0.0230(5) Uani 1 1 d .
C2A C 0.17584(16) 0.24782(13) 0.7768(3) 0.0209(5) Uani 1 1 d .
C4A C 0.26557(17) 0.19399(15) 0.6575(3) 0.0244(5) Uani 1 1 d .
C7A C 0.02768(16) 0.11724(14) 0.5237(3) 0.0223(5) Uani 1 1 d .
C8A C 0.35576(18) 0.18362(17) 0.6466(3) 0.0305(6) Uani 1 1 d .
N1B N 0.13957(15) 0.02599(12) 0.2369(2) 0.0258(5) Uani 1 1 d .
H1B H 0.0859 0.0447 0.1943 0.031 Uiso 1 1 calc R
N2B N 0.24728(15) -0.04078(13) 0.3726(3) 0.0290(5) Uani 1 1 d .
H2B H 0.2772 -0.0740 0.4360 0.035 Uiso 1 1 calc R
C1B C 0.16069(17) -0.02713(14) 0.3332(3) 0.0256(5) Uani 1 1 d .
H1B1 H 0.1207 -0.0515 0.3685 0.031 Uiso 1 1 calc R
C3B C 0.2147(2) 0.04731(16) 0.2136(3) 0.0317(6) Uani 1 1 d .
H3B H 0.2184 0.0847 0.1496 0.038 Uiso 1 1 calc R
C2B C 0.2825(2) 0.00527(18) 0.2986(3) 0.0353(7) Uani 1 1 d .
H2B1 H 0.3430 0.0072 0.3058 0.042 Uiso 1 1 calc R
O1C O 0.0078(2) 0.3974(2) -0.0032(5) 0.1010(14) Uani 1 1 d .
O1D O 0.5000 0.0148(3) 0.2500 0.160(4) 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'
Ni Ni 0.3393 1.1124 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1A Ni1 N1A 179.90(12) 2_556 .
N1A Ni1 O1A 78.44(8) 2_556 2_556
N1A Ni1 O1A 101.63(8) . 2_556
N1A Ni1 O1A 101.63(8) 2_556 .
N1A Ni1 O1A 78.44(8) . .
O1A Ni1 O1A 91.20(11) 2_556 .
N1A Ni1 O3A 77.35(8) 2_556 2_556
N1A Ni1 O3A 102.59(8) . 2_556
O1A Ni1 O3A 155.69(7) 2_556 2_556
O1A Ni1 O3A 91.56(7) . 2_556
N1A Ni1 O3A 102.59(8) 2_556 .
N1A Ni1 O3A 77.35(8) . .
O1A Ni1 O3A 91.56(7) 2_556 .
O1A Ni1 O3A 155.69(7) . .
O3A Ni1 O3A 95.75(10) 2_556 .
C1A O1A Ni1 114.45(16) . .
C6A N1A C2A 121.9(2) . .
C6A N1A Ni1 119.75(17) . .
C2A N1A Ni1 118.09(17) . .
C7A O3A Ni1 114.85(15) . .
C8A O5A H5A 109.5 . .
N1A C6A C5A 121.1(2) . .
N1A C6A C7A 112.9(2) . .
C5A C6A C7A 126.0(2) . .
C8A O6A H6A 109.5 . .
C6A C5A C4A 117.8(2) . .
C6A C5A H5A 121.1 . .
C4A C5A H5A 121.1 . .
C4A C3A C2A 118.1(2) . .
C4A C3A H3A 120.9 . .
C2A C3A H3A 120.9 . .
O2A C1A O1A 126.9(2) . .
O2A C1A C2A 117.5(2) . .
O1A C1A C2A 115.6(2) . .
N1A C2A C3A 120.7(2) . .
N1A C2A C1A 113.1(2) . .
C3A C2A C1A 126.2(2) . .
C3A C4A C5A 120.3(2) . .
C3A C4A C8A 118.8(2) . .
C5A C4A C8A 120.9(2) . .
O4A C7A O3A 127.4(2) . .
O4A C7A C6A 117.7(2) . .
O3A C7A C6A 114.9(2) . .
O6A C8A O5A 126.2(3) . .
O6A C8A C4A 118.4(3) . .
O5A C8A C4A 115.3(3) . .
C1B N1B C3B 108.9(2) . .
C1B N1B H1B 125.6 . .
C3B N1B H1B 125.6 . .
C1B N2B C2B 108.9(2) . .
C1B N2B H2B 125.6 . .
C2B N2B H2B 125.6 . .
N1B C1B N2B 108.5(2) . .
N1B C1B H1B1 125.8 . .
N2B C1B H1B1 125.8 . .
C2B C3B N1B 107.2(2) . .
C2B C3B H3B 126.4 . .
N1B C3B H3B 126.4 . .
C3B C2B N2B 106.6(2) . .
C3B C2B H2B1 126.7 . .
N2B C2B H2B1 126.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1A 1.972(2) 2_556
Ni1 N1A 1.972(2) .
Ni1 O1A 2.1149(18) 2_556
Ni1 O1A 2.1150(18) .
Ni1 O3A 2.1458(18) 2_556
Ni1 O3A 2.1458(18) .
O1A C1A 1.267(3) .
N1A C6A 1.330(3) .
N1A C2A 1.333(3) .
O2A C1A 1.245(3) .
O3A C7A 1.274(3) .
O4A C7A 1.238(3) .
O5A C8A 1.257(4) .
O5A H5A 0.8400 .
C6A C5A 1.388(3) .
C6A C7A 1.519(3) .
O6A C8A 1.235(4) .
O6A H6A 0.8400 .
C5A C4A 1.398(4) .
C5A H5A 0.9500 .
C3A C4A 1.391(4) .
C3A C2A 1.391(4) .
C3A H3A 0.9500 .
C1A C2A 1.512(4) .
C4A C8A 1.507(3) .
N1B C1B 1.317(3) .
N1B C3B 1.368(4) .
N1B H1B 0.8800 .
N2B C1B 1.326(3) .
N2B C2B 1.369(4) .
N2B H2B 0.8800 .
C1B H1B1 0.9500 .
C3B C2B 1.348(4) .
C3B H3B 0.9500 .
C2B H2B1 0.9500 .
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
N1A Ni1 O1A C1A 179.35(18) 2_556
N1A Ni1 O1A C1A -0.58(18) .
O1A Ni1 O1A C1A -102.20(19) 2_556
O3A Ni1 O1A C1A 101.95(18) 2_556
O3A Ni1 O1A C1A -5.7(3) .
N1A Ni1 N1A C6A 44(100) 2_556
O1A Ni1 N1A C6A -92.5(2) 2_556
O1A Ni1 N1A C6A 178.7(2) .
O3A Ni1 N1A C6A 89.7(2) 2_556
O3A Ni1 N1A C6A -3.48(19) .
N1A Ni1 N1A C2A -131(100) 2_556
O1A Ni1 N1A C2A 92.75(19) 2_556
O1A Ni1 N1A C2A 3.90(18) .
O3A Ni1 N1A C2A -85.11(19) 2_556
O3A Ni1 N1A C2A -178.3(2) .
N1A Ni1 O3A C7A -179.88(18) 2_556
N1A Ni1 O3A C7A 0.05(18) .
O1A Ni1 O3A C7A 101.62(18) 2_556
O1A Ni1 O3A C7A 5.2(3) .
O3A Ni1 O3A C7A -101.60(18) 2_556
C2A N1A C6A C5A 2.2(4) .
Ni1 N1A C6A C5A -172.34(19) .
C2A N1A C6A C7A -179.6(2) .
Ni1 N1A C6A C7A 5.8(3) .
N1A C6A C5A C4A 0.5(4) .
C7A C6A C5A C4A -177.4(2) .
Ni1 O1A C1A O2A 177.6(2) .
Ni1 O1A C1A C2A -2.4(3) .
C6A N1A C2A C3A -2.4(4) .
Ni1 N1A C2A C3A 172.25(19) .
C6A N1A C2A C1A 179.2(2) .
Ni1 N1A C2A C1A -6.1(3) .
C4A C3A C2A N1A -0.2(4) .
C4A C3A C2A C1A 178.0(2) .
O2A C1A C2A N1A -174.5(2) .
O1A C1A C2A N1A 5.5(3) .
O2A C1A C2A C3A 7.2(4) .
O1A C1A C2A C3A -172.8(2) .
C2A C3A C4A C5A 2.9(4) .
C2A C3A C4A C8A -174.1(2) .
C6A C5A C4A C3A -3.1(4) .
C6A C5A C4A C8A 173.9(2) .
Ni1 O3A C7A O4A -177.0(2) .
Ni1 O3A C7A C6A 2.8(3) .
N1A C6A C7A O4A 174.3(2) .
C5A C6A C7A O4A -7.7(4) .
N1A C6A C7A O3A -5.6(3) .
C5A C6A C7A O3A 172.5(2) .
C3A C4A C8A O6A 175.9(3) .
C5A C4A C8A O6A -1.1(4) .
C3A C4A C8A O5A -5.5(4) .
C5A C4A C8A O5A 177.5(3) .
C3B N1B C1B N2B -0.1(3) .
C2B N2B C1B N1B -0.1(3) .
C1B N1B C3B C2B 0.2(3) .
N1B C3B C2B N2B -0.2(3) .
C1B N2B C2B C3B 0.2(3) .
