#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/48/2204875.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204875
loop_
_publ_author_name
'You-Fu Zhou'
'Wan-Juan Lin'
'Yong-Gui Huang'
'Mao-Chun Hong'
_publ_section_title
;
 (2,2'-Bipyridine)bis(hydrogen isophthalato)zinc(II)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m177
_journal_page_last               m179
_journal_paper_doi               10.1107/S1600536804033318
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Zn (C8 H5 O4)2 (C10 H8 N2)]'
_chemical_formula_moiety         'C26 H18 N2 O8 Zn'
_chemical_formula_sum            'C26 H18 N2 O8 Zn'
_chemical_formula_weight         551.81
_chemical_name_systematic
;
(2,2'-Bipyridine)bis(hydrogen isophthalato)zinc(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 121.595(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.731(2)
_cell_length_b                   8.1038(7)
_cell_length_c                   15.1428(16)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.20
_cell_volume                     2271.4(4)
_computing_cell_refinement       'SMART and SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Siemens, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruekr SMART CCD'
_diffrn_measurement_method       ω
_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  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3608
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  .796
_exptl_absorpt_correction_T_min  .761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.651
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_gt           0.0814
_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)+(0.0098P)²+22.9335P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                1446
_reflns_number_total             2026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6428.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2204875
_cod_database_fobs_code          2204875
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Zn1 0.5000 0.38566(15) 0.7500 0.0393(4) Uani d S 1 Zn
C1 0.3813(4) 0.2000(8) 0.6658(6) 0.0339(16) Uani d . 1 C
C2 0.3190(4) 0.0957(8) 0.5932(5) 0.0337(16) Uani d . 1 C
C3 0.2996(4) 0.0769(9) 0.4909(6) 0.0424(19) Uani d . 1 C
H3A 0.3279 0.1244 0.4681 0.051 Uiso calc R 1 H
C4 0.2380(4) -0.0128(10) 0.4217(6) 0.050(2) Uani d . 1 C
H4A 0.2247 -0.0233 0.3528 0.060 Uiso calc R 1 H
C5 0.1969(4) -0.0857(9) 0.4557(6) 0.0459(19) Uani d . 1 C
H5A 0.1552 -0.1432 0.4092 0.055 Uiso calc R 1 H
C6 0.2173(3) -0.0738(8) 0.5591(5) 0.0351(17) Uani d . 1 C
C7 0.2780(4) 0.0183(9) 0.6267(6) 0.0360(17) Uani d . 1 C
H7A 0.2914 0.0280 0.6957 0.043 Uiso calc R 1 H
C8 0.1729(4) -0.1609(9) 0.5929(6) 0.0426(19) Uani d . 1 C
C9 0.5505(4) 0.5704(10) 0.6239(6) 0.050(2) Uani d . 1 C
H9A 0.5569 0.4662 0.6041 0.060 Uiso calc R 1 H
C10 0.5666(4) 0.7071(11) 0.5858(6) 0.054(2) Uani d . 1 C
H10A 0.5848 0.6955 0.5426 0.065 Uiso calc R 1 H
C11 0.5552(4) 0.8604(10) 0.6126(6) 0.052(2) Uani d . 1 C
H11A 0.5654 0.9549 0.5877 0.063 Uiso calc R 1 H
C12 0.5284(4) 0.8725(10) 0.6776(6) 0.048(2) Uani d . 1 C
H12A 0.5203 0.9755 0.6967 0.058 Uiso calc R 1 H
C13 0.5138(4) 0.7309(8) 0.7136(5) 0.0336(16) Uani d . 1 C
N1 0.5260(3) 0.5825(7) 0.6886(4) 0.0356(14) Uani d . 1 N
O1 0.4249(3) 0.2478(6) 0.6379(4) 0.0426(13) Uani d . 1 O
O2 0.3919(3) 0.2377(6) 0.7522(4) 0.0421(13) Uani d . 1 O
O3 0.1151(3) -0.2249(8) 0.5336(4) 0.0675(18) Uani d . 1 O
O4 0.2026(3) -0.1640(7) 0.6952(4) 0.0564(16) Uani d . 1 O
H4B 0.1725 -0.1945 0.7088 0.085 Uiso calc R 1 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Zn1 O1 . 6_657 111.0(3) yes
O1 Zn1 N1 . 6_657 121.8(2) yes
O1 Zn1 N1 6_657 6_657 110.3(2) ?
O1 Zn1 N1 . . 110.3(2) ?
O1 Zn1 N1 6_657 . 121.8(2) yes
N1 Zn1 N1 6_657 . 79.0(3) yes
O2 C1 O1 . . 120.8(7) ?
O2 C1 C2 . . 121.0(6) ?
O1 C1 C2 . . 118.3(6) ?
C7 C2 C3 . . 118.9(7) ?
C7 C2 C1 . . 120.0(6) ?
C3 C2 C1 . . 121.1(6) ?
C2 C3 C4 . . 120.4(7) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C5 C4 C3 . . 119.9(7) ?
C5 C4 H4A . . 120.1 ?
C3 C4 H4A . . 120.1 ?
C4 C5 C6 . . 120.4(7) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C5 C6 C7 . . 119.1(7) ?
C5 C6 C8 . . 118.3(7) ?
C7 C6 C8 . . 122.6(7) ?
C2 C7 C6 . . 121.3(7) ?
C2 C7 H7A . . 119.4 ?
C6 C7 H7A . . 119.4 ?
O3 C8 O4 . . 122.5(7) ?
O3 C8 C6 . . 123.7(7) ?
O4 C8 C6 . . 113.8(7) ?
N1 C9 C10 . . 122.2(8) ?
N1 C9 H9A . . 118.9 ?
C10 C9 H9A . . 118.9 ?
C11 C10 C9 . . 118.8(7) ?
C11 C10 H10A . . 120.6 ?
C9 C10 H10A . . 120.6 ?
C10 C11 C12 . . 118.9(7) ?
C10 C11 H11A . . 120.6 ?
C12 C11 H11A . . 120.6 ?
C13 C12 C11 . . 119.6(7) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
N1 C13 C12 . . 121.3(6) ?
N1 C13 C13 . 6_657 115.1(4) ?
C12 C13 C13 . 6_657 123.6(4) ?
C13 N1 C9 . . 119.2(6) ?
C13 N1 Zn1 . . 115.4(4) ?
C9 N1 Zn1 . . 125.3(5) ?
C1 O1 Zn1 . . 107.9(4) ?
C8 O4 H4B . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 . 1.972(5) yes
Zn1 O1 6_657 1.972(5) yes
Zn1 N1 6_657 2.067(5) yes
Zn1 N1 . 2.067(5) yes
C1 O2 . 1.242(8) ?
C1 O1 . 1.283(8) ?
C1 C2 . 1.482(10) ?
C2 C7 . 1.384(9) ?
C2 C3 . 1.385(9) ?
C3 C4 . 1.397(10) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.377(10) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.388(10) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.390(9) ?
C6 C8 . 1.486(10) ?
C7 H7A . 0.9300 ?
C8 O3 . 1.214(9) ?
C8 O4 . 1.330(8) ?
C9 N1 . 1.343(9) ?
C9 C10 . 1.376(11) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.369(11) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.385(11) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.378(10) ?
C12 H12A . 0.9300 ?
C13 N1 . 1.329(8) ?
C13 C13 6_657 1.504(13) ?
O4 H4B . 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4B O2 8_547 0.82 1.86 2.684(7) 177
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O2 C1 C2 C7 . . -9.8(10)
O1 C1 C2 C7 . . 168.9(6)
O2 C1 C2 C3 . . 168.6(6)
O1 C1 C2 C3 . . -12.7(10)
C7 C2 C3 C4 . . 2.7(11)
C1 C2 C3 C4 . . -175.8(7)
C2 C3 C4 C5 . . -1.2(12)
C3 C4 C5 C6 . . -1.5(12)
C4 C5 C6 C7 . . 2.6(11)
C4 C5 C6 C8 . . -177.3(7)
C3 C2 C7 C6 . . -1.6(10)
C1 C2 C7 C6 . . 176.9(6)
C5 C6 C7 C2 . . -1.1(10)
C8 C6 C7 C2 . . 178.9(6)
C5 C6 C8 O3 . . -9.4(11)
C7 C6 C8 O3 . . 170.7(7)
C5 C6 C8 O4 . . 170.1(6)
C7 C6 C8 O4 . . -9.9(10)
N1 C9 C10 C11 . . -1.8(12)
C9 C10 C11 C12 . . 0.3(12)
C10 C11 C12 C13 . . 0.0(12)
C11 C12 C13 N1 . . 1.1(11)
C11 C12 C13 C13 . 6_657 178.5(8)
C12 C13 N1 C9 . . -2.5(10)
C13 C13 N1 C9 6_657 . 179.9(7)
C12 C13 N1 Zn1 . . -179.7(5)
C13 C13 N1 Zn1 6_657 . 2.7(9)
C10 C9 N1 C13 . . 2.9(11)
C10 C9 N1 Zn1 . . 179.8(6)
O1 Zn1 N1 C13 . . 119.0(5)
O1 Zn1 N1 C13 6_657 . -108.3(5)
N1 Zn1 N1 C13 6_657 . -1.0(4)
O1 Zn1 N1 C9 . . -58.0(6)
O1 Zn1 N1 C9 6_657 . 74.7(6)
N1 Zn1 N1 C9 6_657 . -178.0(7)
O2 C1 O1 Zn1 . . -2.2(8)
C2 C1 O1 Zn1 . . 179.1(5)
O1 Zn1 O1 C1 6_657 . 80.6(4)
N1 Zn1 O1 C1 6_657 . -51.8(5)
N1 Zn1 O1 C1 . . -141.3(4)
