#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/25/8102528.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_8102528
loop_
_publ_author_name
'Ni Wang'
'Ji-Jiang Wang'
'Peng Zhang'
'Cai-Xia Meng'
'Xiao-Ning Zhang'
_publ_section_title
;
 Crystal structure of
 (2,2'-bipyridine)-bis(1H-1,2-phenylenediacetato)zinc(II),
 Zn(C10H9O4)2(C10H8N2)
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              605
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C60 H52 N4 O16 Zn2'
_chemical_formula_weight         1215.80
_chemical_name_systematic
;
(2,2'-bipyridine) zinc(II) bis-(1H-1,2-phenylenediacetic), 
Zn(C₁₀H₉O₄)₂(C₁₀H₈N₂)
;
_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                 111.975(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.398(4)
_cell_length_b                   8.6224(18)
_cell_length_c                   20.785(4)
_cell_measurement_reflns_used    4010
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.68
_cell_volume                     2725.3(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  0.8841
_exptl_absorpt_correction_T_min  0.7655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0089(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0590
_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)+(0.1480P)²+4.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2163
_reflns_number_gt                2253
_reflns_number_total             2536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2735.cff
_cod_data_source_block           d
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to
'constr' 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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2725.4(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8102528
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.06039(7) 0.2500 0.0411(3) Uani 1 2 d S . .
O1 O -0.0827(3) 0.2065(6) 0.1589(3) 0.0937(14) Uani 1 1 d . . .
O2 O 0.0530(3) 0.1725(6) 0.1701(2) 0.0875(13) Uani 1 1 d . . .
O3 O -0.1893(4) 0.3191(8) -0.1289(3) 0.119(2) Uani 1 1 d . . .
O4 O -0.2626(3) 0.1667(8) -0.0835(4) 0.120(2) Uani 1 1 d . . .
H4 H -0.3034 0.2256 -0.1039 0.180 Uiso 1 1 calc R . .
N1 N 0.0893(3) -0.1478(6) 0.2721(3) 0.0702(12) Uani 1 1 d . . .
C1 C -0.0186(4) 0.2307(7) 0.1390(3) 0.0686(14) Uani 1 1 d . . .
C2 C -0.0361(6) 0.3366(9) 0.0767(4) 0.092(2) Uani 1 1 d . . .
H2A H -0.0986 0.3351 0.0491 0.111 Uiso 1 1 calc R . .
H2B H -0.0207 0.4417 0.0934 0.111 Uiso 1 1 calc R . .
C3 C 0.0127(4) 0.2962(7) 0.0302(3) 0.0680(14) Uani 1 1 d . . .
C4 C 0.0946(4) 0.3577(8) 0.0442(4) 0.0820(17) Uani 1 1 d . . .
H4A H 0.1189 0.4214 0.0828 0.098 Uiso 1 1 calc R . .
C5 C 0.1420(5) 0.3285(11) 0.0033(5) 0.100(2) Uani 1 1 d . . .
H5 H 0.1981 0.3699 0.0150 0.119 Uiso 1 1 calc R . .
C6 C 0.1066(5) 0.2388(11) -0.0544(4) 0.096(2) Uani 1 1 d . . .
H6 H 0.1377 0.2193 -0.0829 0.115 Uiso 1 1 calc R . .
C7 C 0.0245(6) 0.1777(9) -0.0696(3) 0.096(2) Uani 1 1 d . . .
H7 H 0.0006 0.1165 -0.1091 0.115 Uiso 1 1 calc R . .
C8 C -0.0247(4) 0.2027(7) -0.0288(3) 0.0718(15) Uani 1 1 d . . .
C9 C -0.1116(5) 0.1269(10) -0.0456(5) 0.106(3) Uani 1 1 d . . .
H9A H -0.1181 0.1014 -0.0023 0.127 Uiso 1 1 calc R . .
H9B H -0.1111 0.0299 -0.0691 0.127 Uiso 1 1 calc R . .
C10 C -0.1910(4) 0.2175(8) -0.0895(3) 0.0764(16) Uani 1 1 d . . .
C11 C 0.1753(4) -0.1418(11) 0.2896(4) 0.090(2) Uani 1 1 d . . .
H11 H 0.2018 -0.0446 0.2968 0.108 Uiso 1 1 calc R . .
C12 C 0.2271(5) -0.2663(14) 0.2978(4) 0.103(3) Uani 1 1 d . . .
H12 H 0.2877 -0.2562 0.3109 0.124 Uiso 1 1 calc R . .
C13 C 0.1877(6) -0.4088(13) 0.2860(5) 0.106(3) Uani 1 1 d . . .
H13 H 0.2211 -0.4978 0.2896 0.127 Uiso 1 1 calc R . .
C14 C 0.0960(6) -0.4201(9) 0.2684(4) 0.092(2) Uani 1 1 d . . .
H14 H 0.0686 -0.5164 0.2622 0.111 Uiso 1 1 calc R . .
C15 C 0.0487(4) -0.2878(6) 0.2607(3) 0.0644(13) Uani 1 1 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
N1 Zn1 N1 74.3(2) . 2 ?
N1 Zn1 O1 97.64(19) . 2 ?
N1 Zn1 O1 139.20(18) 2 2 ?
N1 Zn1 O1 139.20(18) . . ?
N1 Zn1 O1 97.64(19) 2 . ?
O1 Zn1 O1 112.1(3) 2 . ?
N1 Zn1 O2 95.06(17) . . ?
N1 Zn1 O2 124.54(18) 2 . ?
O1 Zn1 O2 95.66(17) 2 . ?
O1 Zn1 O2 56.11(16) . . ?
N1 Zn1 O2 124.54(18) . 2 ?
N1 Zn1 O2 95.06(17) 2 2 ?
O1 Zn1 O2 56.11(16) 2 2 ?
O1 Zn1 O2 95.67(17) . 2 ?
O2 Zn1 O2 131.5(3) . 2 ?
C1 O1 Zn1 93.0(4) . . ?
C1 O2 Zn1 90.4(4) . . ?
C10 O4 H4 109.5 . . ?
C11 N1 C15 119.2(6) . . ?
C11 N1 Zn1 124.8(5) . . ?
C15 N1 Zn1 115.7(3) . . ?
O2 C1 O1 120.5(6) . . ?
O2 C1 C2 122.5(6) . . ?
O1 C1 C2 117.1(5) . . ?
C3 C2 C1 115.5(5) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C8 118.8(6) . . ?
C4 C3 C2 119.2(7) . . ?
C8 C3 C2 122.0(6) . . ?
C3 C4 C5 122.3(7) . . ?
C3 C4 H4A 118.8 . . ?
C5 C4 H4A 118.8 . . ?
C6 C5 C4 119.7(7) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 118.8(7) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 123.0(7) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C7 C8 C3 117.3(7) . . ?
C7 C8 C9 120.9(7) . . ?
C3 C8 C9 121.7(7) . . ?
C8 C9 C10 116.8(6) . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
O3 C10 O4 124.1(6) . . ?
O3 C10 C9 123.7(7) . . ?
O4 C10 C9 112.0(6) . . ?
N1 C11 C12 124.4(8) . . ?
N1 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C11 C12 C13 117.5(7) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C12 C13 C14 119.7(8) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 118.7(8) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 N1 120.4(6) . . ?
C14 C15 C15 122.5(5) . 2 ?
N1 C15 C15 117.0(3) . 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 N1 2.253(5) . ?
Zn1 N1 2.253(5) 2 ?
Zn1 O1 2.257(5) 2 ?
Zn1 O1 2.257(5) . ?
Zn1 O2 2.351(5) . ?
Zn1 O2 2.352(5) 2 ?
O1 C1 1.282(7) . ?
O2 C1 1.216(7) . ?
O3 C10 1.207(8) . ?
O4 C10 1.301(8) . ?
O4 H4 0.8200 . ?
N1 C11 1.319(8) . ?
N1 C15 1.356(7) . ?
C1 C2 1.521(9) . ?
C2 C3 1.508(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.369(9) . ?
C3 C8 1.403(9) . ?
C4 C5 1.374(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.361(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(10) . ?
C9 C10 1.501(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.340(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.411(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(8) . ?
C14 H14 0.9300 . ?
C15 C15 1.488(11) 2 ?
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
O4 H4 O1 0.82 1.88 2.666(7) 159.9 7_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 Zn1 O1 C1 -52.9(5) . . . . ?
N1 Zn1 O1 C1 -127.7(4) 2 . . . ?
O1 Zn1 O1 C1 80.8(4) 2 . . . ?
O2 Zn1 O1 C1 -0.9(3) . . . . ?
O2 Zn1 O1 C1 136.4(4) 2 . . . ?
N1 Zn1 O2 C1 149.8(4) . . . . ?
N1 Zn1 O2 C1 75.4(4) 2 . . . ?
O1 Zn1 O2 C1 -112.0(4) 2 . . . ?
O1 Zn1 O2 C1 0.9(4) . . . . ?
O2 Zn1 O2 C1 -63.3(4) 2 . . . ?
N1 Zn1 N1 C11 175.8(7) 2 . . . ?
O1 Zn1 N1 C11 -45.1(6) 2 . . . ?
O1 Zn1 N1 C11 92.3(6) . . . . ?
O2 Zn1 N1 C11 51.3(5) . . . . ?
O2 Zn1 N1 C11 -98.9(5) 2 . . . ?
N1 Zn1 N1 C15 1.3(3) 2 . . . ?
O1 Zn1 N1 C15 140.4(4) 2 . . . ?
O1 Zn1 N1 C15 -82.2(5) . . . . ?
O2 Zn1 N1 C15 -123.2(4) . . . . ?
O2 Zn1 N1 C15 86.6(4) 2 . . . ?
Zn1 O2 C1 O1 -1.6(6) . . . . ?
Zn1 O2 C1 C2 177.1(6) . . . . ?
Zn1 O1 C1 O2 1.7(6) . . . . ?
Zn1 O1 C1 C2 -177.1(5) . . . . ?
O2 C1 C2 C3 35.0(10) . . . . ?
O1 C1 C2 C3 -146.3(7) . . . . ?
C1 C2 C3 C4 -88.8(8) . . . . ?
C1 C2 C3 C8 93.9(8) . . . . ?
C8 C3 C4 C5 -1.3(9) . . . . ?
C2 C3 C4 C5 -178.6(6) . . . . ?
C3 C4 C5 C6 1.7(11) . . . . ?
C4 C5 C6 C7 -0.9(12) . . . . ?
C5 C6 C7 C8 -0.1(11) . . . . ?
C6 C7 C8 C3 0.5(10) . . . . ?
C6 C7 C8 C9 -176.7(7) . . . . ?
C4 C3 C8 C7 0.2(8) . . . . ?
C2 C3 C8 C7 177.5(6) . . . . ?
C4 C3 C8 C9 177.4(6) . . . . ?
C2 C3 C8 C9 -5.3(8) . . . . ?
C7 C8 C9 C10 -93.6(9) . . . . ?
C3 C8 C9 C10 89.3(9) . . . . ?
C8 C9 C10 O3 24.5(13) . . . . ?
C8 C9 C10 O4 -159.8(8) . . . . ?
C15 N1 C11 C12 -0.6(11) . . . . ?
Zn1 N1 C11 C12 -174.9(6) . . . . ?
N1 C11 C12 C13 1.1(12) . . . . ?
C11 C12 C13 C14 -2.1(13) . . . . ?
C12 C13 C14 C15 2.8(13) . . . . ?
C13 C14 C15 N1 -2.2(11) . . . . ?
C13 C14 C15 C15 177.3(8) . . . 2 ?
C11 N1 C15 C14 1.2(9) . . . . ?
Zn1 N1 C15 C14 176.0(5) . . . . ?
C11 N1 C15 C15 -178.4(6) . . . 2 ?
Zn1 N1 C15 C15 -3.5(8) . . . 2 ?
