#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:10:05 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179778 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/74/7007489.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_7007489
loop_
_publ_author_name
'Chen, Chun-Long'
'Ellsworth, Joseph M.'
'Goforth, Andrea M.'
'Smith, Mark D.'
'Su, Cheng-Yong'
'Zur Loye, Hans-Conrad'
_publ_section_title
;
 A new 2-carboxylate-substituted 4,4'-bipyridine ligand: coordination
 chemistry of 4,4'-bipyridine-2-carboxylic acid and its synthetic
 intermediate 2-methyl-4,4'-bipyridine.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5278
_journal_page_last               5286
_journal_paper_doi               10.1039/b606280f
_journal_year                    2006
_chemical_formula_moiety         'C22 H18 N4 O6 Zn, 2(H2 O)'
_chemical_formula_sum            'C22 H22 N4 O8 Zn'
_chemical_formula_weight         535.81
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.4456(12)
_cell_length_b                   7.6438(4)
_cell_length_c                   14.8027(9)
_cell_measurement_reflns_used    6439
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      26.358
_cell_measurement_theta_min      2.758
_cell_volume                     2195.9(2)
_computing_cell_refinement       'SAINT+ NT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 1998)'
_computing_data_reduction        'SAINT+ NT V6.22'
_computing_molecular_graphics    'SHELXTL V6.1 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8881
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0277
_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)+(0.0461P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                2063
_reflns_number_total             2263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606280f.txt
_cod_data_source_block           c12171m
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7007489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Zn1 Zn 0.2500 0.30577(3) 0.5000 0.01988(11) Uani 1 2 d S . .
C1 C 0.33109(9) 0.20437(19) 0.34908(11) 0.0198(3) Uani 1 1 d . . .
C2 C 0.38022(9) 0.20345(19) 0.28527(11) 0.0205(3) Uani 1 1 d . . .
H2 H 0.3713 0.1461 0.2288 0.020(4) Uiso 1 1 calc R . .
C3 C 0.44286(9) 0.2878(2) 0.30503(12) 0.0212(3) Uani 1 1 d . . .
C4 C 0.45317(9) 0.3703(2) 0.38831(11) 0.0263(4) Uani 1 1 d . . .
H4 H 0.4958 0.4258 0.4048 0.034(5) Uiso 1 1 calc R . .
C5 C 0.40060(9) 0.3709(2) 0.44700(11) 0.0260(4) Uani 1 1 d . . .
H5 H 0.4074 0.4317 0.5028 0.036(5) Uiso 1 1 calc R . .
C6 C 0.26303(8) 0.1065(2) 0.33467(10) 0.0205(3) Uani 1 1 d . . .
C7 C 0.61484(9) 0.2596(2) 0.20178(13) 0.0287(4) Uani 1 1 d . . .
H7 H 0.6612 0.2319 0.2205 0.017(4) Uiso 1 1 calc R . .
C8 C 0.56531(9) 0.2556(2) 0.26554(12) 0.0263(4) Uani 1 1 d . . .
H8 H 0.5780 0.2289 0.3270 0.027(5) Uiso 1 1 calc R . .
C9 C 0.49718(9) 0.2910(2) 0.23859(12) 0.0225(4) Uani 1 1 d . . .
C10 C 0.48065(10) 0.3303(2) 0.14833(12) 0.0269(4) Uani 1 1 d . . .
H10 H 0.4345 0.3537 0.1271 0.021(4) Uiso 1 1 calc R . .
C11 C 0.53415(10) 0.3344(2) 0.08982(12) 0.0295(4) Uani 1 1 d . . .
H11 H 0.5231 0.3630 0.0282 0.034(5) Uiso 1 1 calc R . .
N1 N 0.34055(7) 0.28918(16) 0.42834(9) 0.0207(3) Uani 1 1 d . . .
N2 N 0.59970(8) 0.30077(18) 0.11513(11) 0.0299(4) Uani 1 1 d . . .
O1 O 0.22240(6) 0.12110(15) 0.39829(7) 0.0231(3) Uani 1 1 d . . .
O2 O 0.25236(6) 0.01996(14) 0.26484(8) 0.0252(3) Uani 1 1 d . . .
O3 O 0.20747(7) 0.49714(16) 0.41024(8) 0.0294(3) Uani 1 1 d D . .
H3A H 0.2019(13) 0.5953(14) 0.4267(15) 0.056(7) Uiso 1 1 d D . .
H3B H 0.2183(10) 0.504(3) 0.3597(7) 0.037(6) Uiso 1 1 d D . .
O4 O 0.16108(7) 0.81259(16) 0.45079(10) 0.0300(3) Uani 1 1 d D . .
H4A H 0.1822(10) 0.8968(18) 0.4413(14) 0.040(6) Uiso 1 1 d D . .
H4B H 0.1529(13) 0.824(3) 0.5020(7) 0.046(7) Uiso 1 1 d D . .
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'
Zn Zn 0.2839 1.4301 '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 Zn1 O1 95.96(6) . 2_556 ?
O1 Zn1 O3 170.40(4) . 2_556 ?
O1 Zn1 O3 86.69(5) 2_556 2_556 ?
O1 Zn1 O3 86.69(5) . . ?
O1 Zn1 O3 170.40(4) 2_556 . ?
O3 Zn1 O3 92.21(7) 2_556 . ?
O1 Zn1 N1 97.77(5) . 2_556 ?
O1 Zn1 N1 77.56(5) 2_556 2_556 ?
O3 Zn1 N1 91.81(5) 2_556 2_556 ?
O3 Zn1 N1 92.95(5) . 2_556 ?
O1 Zn1 N1 77.56(5) . . ?
O1 Zn1 N1 97.77(5) 2_556 . ?
O3 Zn1 N1 92.95(5) 2_556 . ?
O3 Zn1 N1 91.81(5) . . ?
N1 Zn1 N1 173.13(7) 2_556 . ?
N1 C1 C2 122.39(15) . . ?
N1 C1 C6 115.45(13) . . ?
C2 C1 C6 122.15(14) . . ?
C1 C2 C3 119.07(15) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 118.21(15) . . ?
C4 C3 C9 120.71(15) . . ?
C2 C3 C9 121.08(15) . . ?
C5 C4 C3 119.21(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 122.63(16) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
O2 C6 O1 126.01(15) . . ?
O2 C6 C1 118.67(14) . . ?
O1 C6 C1 115.32(14) . . ?
N2 C7 C8 122.45(17) . . ?
N2 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C9 C8 C7 119.38(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.63(16) . . ?
C8 C9 C3 120.79(16) . . ?
C10 C9 C3 120.58(16) . . ?
C9 C10 C11 117.77(17) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
N2 C11 C10 123.99(17) . . ?
N2 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C5 N1 C1 118.41(14) . . ?
C5 N1 Zn1 127.71(11) . . ?
C1 N1 Zn1 113.21(11) . . ?
C11 N2 C7 117.76(15) . . ?
C6 O1 Zn1 116.45(10) . . ?
Zn1 O3 H3A 120.9(18) . . ?
Zn1 O3 H3B 121.5(15) . . ?
H3A O3 H3B 106(2) . . ?
H4A O4 H4B 103(2) . . ?
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
Zn1 O1 2.1086(11) . ?
Zn1 O1 2.1086(11) 2_556 ?
Zn1 O3 2.1099(12) 2_556 ?
Zn1 O3 2.1099(12) . ?
Zn1 N1 2.1155(14) 2_556 ?
Zn1 N1 2.1155(14) . ?
C1 N1 1.343(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.524(2) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 C9 1.488(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.338(2) . ?
C5 H5 0.9500 . ?
C6 O2 1.2337(19) . ?
C6 O1 1.2716(19) . ?
C7 N2 1.336(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C10 C11 1.395(2) . ?
C10 H10 0.9500 . ?
C11 N2 1.331(3) . ?
C11 H11 0.9500 . ?
O3 H3A 0.799(8) . ?
O3 H3B 0.792(8) . ?
O4 H4A 0.781(8) . ?
O4 H4B 0.789(8) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O4 0.799(8) 1.884(11) 2.6562(17) 162(3) .
O3 H3B O2 0.792(8) 1.971(9) 2.7564(17) 171(2) 7
O4 H4A O1 0.781(8) 2.004(9) 2.7753(17) 169(2) 1_565
O4 H4B N2 0.789(8) 2.031(12) 2.777(2) 158(2) 3_455
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 2.5(2) . . . . ?
C6 C1 C2 C3 -176.49(14) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C2 C3 C9 -179.80(14) . . . . ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C9 C3 C4 C5 177.43(15) . . . . ?
C3 C4 C5 N1 2.5(3) . . . . ?
N1 C1 C6 O2 -177.06(14) . . . . ?
C2 C1 C6 O2 2.0(2) . . . . ?
N1 C1 C6 O1 2.0(2) . . . . ?
C2 C1 C6 O1 -178.95(14) . . . . ?
N2 C7 C8 C9 1.8(3) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C3 179.98(15) . . . . ?
C4 C3 C9 C8 46.2(2) . . . . ?
C2 C3 C9 C8 -134.25(17) . . . . ?
C4 C3 C9 C10 -133.43(18) . . . . ?
C2 C3 C9 C10 46.1(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C3 C9 C10 C11 178.78(14) . . . . ?
C9 C10 C11 N2 0.9(3) . . . . ?
C4 C5 N1 C1 -0.4(2) . . . . ?
C4 C5 N1 Zn1 -170.40(13) . . . . ?
C2 C1 N1 C5 -2.1(2) . . . . ?
C6 C1 N1 C5 176.90(14) . . . . ?
C2 C1 N1 Zn1 169.27(12) . . . . ?
C6 C1 N1 Zn1 -11.70(16) . . . . ?
O1 Zn1 N1 C5 -177.27(15) . . . . ?
O1 Zn1 N1 C5 -82.84(14) 2_556 . . . ?
O3 Zn1 N1 C5 4.21(14) 2_556 . . . ?
O3 Zn1 N1 C5 96.53(14) . . . . ?
O1 Zn1 N1 C1 12.31(10) . . . . ?
O1 Zn1 N1 C1 106.73(11) 2_556 . . . ?
O3 Zn1 N1 C1 -166.21(11) 2_556 . . . ?
O3 Zn1 N1 C1 -73.90(11) . . . . ?
C10 C11 N2 C7 0.4(3) . . . . ?
C8 C7 N2 C11 -1.8(3) . . . . ?
O2 C6 O1 Zn1 -171.98(12) . . . . ?
C1 C6 O1 Zn1 9.01(17) . . . . ?
O1 Zn1 O1 C6 -108.43(12) 2_556 . . . ?
O3 Zn1 O1 C6 80.83(12) . . . . ?
N1 Zn1 O1 C6 173.36(11) 2_556 . . . ?
N1 Zn1 O1 C6 -11.76(11) . . . . ?
