#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/38/2233882.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_2233882
loop_
_publ_author_name
'Zhang, Bi-Song'
'Zhu, Hong-Line'
'Li, Jun'
'Dai, Dong-Dong'
'Peng, Yi-Bao'
_publ_section_title
;
 (2,2'-Bipyridine-κ²N,N')bis(4-chlorobenzoato-κO)zinc
;
_journal_coeditor_code           HY2516
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m321
_journal_page_last               m322
_journal_paper_doi               10.1107/S160053681200699X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Zn (C7 H4 Cl O2)2 (C10 H8 N2)]'
_chemical_formula_moiety         'C24 H16 Cl2 N2 O4 Zn'
_chemical_formula_sum            'C24 H16 Cl2 N2 O4 Zn'
_chemical_formula_weight         532.68
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')bis(4-chlorobenzoato-
κO)zinc(II)
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 107.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.453(2)
_cell_length_b                   8.4896(17)
_cell_length_c                   12.337(3)
_cell_measurement_reflns_used    6683
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.04
_cell_volume                     1146.4(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics
'XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotation anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8641
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.360
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2012
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0411
_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)+(0.0510P)²+0.4320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                1560
_reflns_number_total             2012
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2516.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2233882
_cod_database_fobs_code          2233882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
Zn Zn1 0.0000 0.78102(6) 0.2500 0.0564(2) Uani d S 1 2
Cl Cl2 0.59680(10) 1.35611(14) 0.61254(11) 0.0912(4) Uani d . 1 1
O O1 0.1788(3) 0.9459(3) 0.2186(2) 0.0738(7) Uani d . 1 1
O O2 0.1206(2) 0.8948(3) 0.3696(2) 0.0650(7) Uani d . 1 1
C C1 -0.1402(4) 0.6021(6) 0.3867(4) 0.0889(13) Uani d U 1 1
H H1 -0.1636 0.7013 0.4048 0.107 Uiso calc R 1 1
C C2 -0.1780(5) 0.4710(8) 0.4330(5) 0.122(2) Uani d U 1 1
H H2 -0.2269 0.4814 0.4808 0.146 Uiso calc R 1 1
C C3 -0.1427(7) 0.3267(9) 0.4076(6) 0.144(3) Uani d U 1 1
H H3 -0.1657 0.2369 0.4394 0.172 Uiso calc R 1 1
C C4 -0.0731(6) 0.3138(6) 0.3351(5) 0.121(2) Uani d U 1 1
H H4 -0.0493 0.2150 0.3168 0.145 Uiso calc R 1 1
C C5 -0.0377(4) 0.4489(4) 0.2888(3) 0.0827(13) Uani d U 1 1
N N1 -0.0713(3) 0.5916(3) 0.3171(3) 0.0686(8) Uani d U 1 1
C C6 0.2915(3) 1.0622(4) 0.3941(3) 0.0512(8) Uani d . 1 1
C C7 0.3756(4) 1.1328(5) 0.3489(3) 0.0679(10) Uani d . 1 1
H H7 0.3691 1.1184 0.2726 0.082 Uiso calc R 1 1
C C8 0.4688(4) 1.2242(5) 0.4152(4) 0.0741(11) Uani d . 1 1
H H8 0.5246 1.2720 0.3842 0.089 Uiso calc R 1 1
C C9 0.4779(3) 1.2436(4) 0.5275(4) 0.0629(10) Uani d . 1 1
C C10 0.3952(4) 1.1763(5) 0.5739(3) 0.0690(10) Uani d . 1 1
H H10 0.4017 1.1915 0.6501 0.083 Uiso calc R 1 1
C C11 0.3019(3) 1.0853(4) 0.5063(3) 0.0614(9) Uani d . 1 1
H H11 0.2455 1.0391 0.5375 0.074 Uiso calc R 1 1
C C12 0.1909(3) 0.9613(4) 0.3207(3) 0.0553(8) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
O2 Zn1 O2 . 2 120.76(15)
O2 Zn1 N1 . . 110.75(11)
O2 Zn1 N1 2 . 114.15(11)
O2 Zn1 N1 . 2 114.15(11)
O2 Zn1 N1 2 2 110.75(11)
N1 Zn1 N1 . 2 78.9(2)
O2 Zn1 C12 . . 28.13(10)
O2 Zn1 C12 2 . 107.47(11)
N1 Zn1 C12 . . 135.29(12)
N1 Zn1 C12 2 . 101.44(12)
O2 Zn1 C12 . 2 107.47(11)
O2 Zn1 C12 2 2 28.13(10)
N1 Zn1 C12 . 2 101.44(12)
N1 Zn1 C12 2 2 135.29(12)
C12 Zn1 C12 . 2 107.90(14)
O2 Zn1 O1 . . 55.55(9)
O2 Zn1 O1 2 . 91.94(10)
N1 Zn1 O1 . . 153.21(11)
N1 Zn1 O1 2 . 86.47(11)
C12 Zn1 O1 . . 27.42(9)
C12 Zn1 O1 2 . 104.74(10)
O2 Zn1 O1 . 2 91.94(10)
O2 Zn1 O1 2 2 55.55(9)
N1 Zn1 O1 . 2 86.47(11)
N1 Zn1 O1 2 2 153.21(11)
C12 Zn1 O1 . 2 104.74(10)
C12 Zn1 O1 2 2 27.42(9)
O1 Zn1 O1 . 2 114.90(12)
C12 O1 Zn1 . . 76.2(2)
C12 O2 Zn1 . . 105.5(2)
N1 C1 C2 . . 122.1(5)
N1 C1 H1 . . 118.9
C2 C1 H1 . . 118.9
C3 C2 C1 . . 118.9(6)
C3 C2 H2 . . 120.5
C1 C2 H2 . . 120.5
C2 C3 C4 . . 119.6(5)
C2 C3 H3 . . 120.2
C4 C3 H3 . . 120.2
C3 C4 C5 . . 119.9(6)
C3 C4 H4 . . 120.1
C5 C4 H4 . . 120.1
N1 C5 C4 . . 119.6(5)
N1 C5 C5 . 2 115.9(2)
C4 C5 C5 . 2 124.5(4)
C1 N1 C5 . . 119.8(4)
C1 N1 Zn1 . . 125.5(3)
C5 N1 Zn1 . . 114.6(3)
C11 C6 C7 . . 118.8(3)
C11 C6 C12 . . 120.9(3)
C7 C6 C12 . . 120.3(3)
C8 C7 C6 . . 120.9(4)
C8 C7 H7 . . 119.6
C6 C7 H7 . . 119.6
C9 C8 C7 . . 119.0(4)
C9 C8 H8 . . 120.5
C7 C8 H8 . . 120.5
C10 C9 C8 . . 121.2(4)
C10 C9 Cl2 . . 119.5(3)
C8 C9 Cl2 . . 119.3(3)
C9 C10 C11 . . 119.3(4)
C9 C10 H10 . . 120.4
C11 C10 H10 . . 120.4
C6 C11 C10 . . 120.8(4)
C6 C11 H11 . . 119.6
C10 C11 H11 . . 119.6
O1 C12 O2 . . 122.8(3)
O1 C12 C6 . . 120.7(3)
O2 C12 C6 . . 116.5(3)
O1 C12 Zn1 . . 76.4(2)
O2 C12 Zn1 . . 46.41(16)
C6 C12 Zn1 . . 162.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 O2 . 1.954(2)
Zn1 N1 . 2.082(3)
Zn1 O1 . 2.602(3)
Cl2 C9 . 1.740(4)
O1 C12 . 1.233(4)
O2 C12 . 1.272(4)
C1 N1 . 1.329(6)
C1 C2 . 1.377(6)
C1 H1 . 0.9300
C2 C3 . 1.356(10)
C2 H2 . 0.9300
C3 C4 . 1.366(11)
C3 H3 . 0.9300
C4 C5 . 1.394(6)
C4 H4 . 0.9300
C5 N1 . 1.347(5)
C5 C5 2 1.466(10)
C6 C11 . 1.368(5)
C6 C7 . 1.384(5)
C6 C12 . 1.506(5)
C7 C8 . 1.377(6)
C7 H7 . 0.9300
C8 C9 . 1.368(6)
C8 H8 . 0.9300
C9 C10 . 1.368(5)
C10 C11 . 1.382(5)
C10 H10 . 0.9300
C11 H11 . 0.9300
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
_geom_hbond_publ_flag
C1 H1 O1 2_555 0.930 2.550 3.172(6) 125 yes
C3 H3 O2 3_566 0.930 2.520 3.278(5) 139 yes
C11 H11 O1 4_576 0.930 2.570 3.330(5) 139 yes
