#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220923.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_2220923
loop_
_publ_author_name
'Tan, Kong Wai'
'Ng, Chew Hee'
'Maah, Mohd Jamil'
'Ng, Seik Weng'
_publ_section_title
;
 (2,2'-Bipyridine-κ²N,N')(4-hydroxy-2-oxidobenzaldehyde
 thiosemicarbazonato-κ³O²,N¹,S)zinc(II)
;
_journal_coeditor_code           TK2348
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m143
_journal_paper_doi               10.1107/S1600536808043973
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (C8 H7 N3 O2 S) (C10 H8 N2)]'
_chemical_formula_moiety         'C18 H15 N5 O2 S Zn'
_chemical_formula_sum            'C18 H15 N5 O2 S Zn'
_chemical_formula_weight         430.78
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')(4-hydroxy-2-oxidobenzaldehyde
thiosemicarbazonato-κ³O²,N¹,S)zinc(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 113.646(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1256(4)
_cell_length_b                   7.0478(2)
_cell_length_c                   17.6387(5)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      2.3
_cell_volume                     1836.33(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.086
_diffrn_reflns_av_sigmaI/netI    0.085
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15773
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.96
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.098
_refine_ls_R_factor_gt           0.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1071P)²+3.3408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.169
_refine_ls_wR_factor_ref         0.195
_reflns_number_gt                2919
_reflns_number_total             4191
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2348.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220923
_cod_database_fobs_code          2220923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.26010(4) 0.61341(9) 0.78222(4) 0.0186(2) Uani d . 1 . .
S S1 0.35671(10) 0.8297(2) 0.75159(9) 0.0239(3) Uani d . 1 . .
O O1 0.1393(2) 0.4912(5) 0.7423(2) 0.0221(8) Uani d . 1 . .
O O2 -0.0804(3) -0.0017(6) 0.6388(2) 0.0238(8) Uani d . 1 . .
H H2 -0.0941 0.0325 0.6780 0.036 Uiso calc R 1 . .
N N1 0.2953(3) 0.4436(7) 0.7058(3) 0.0213(10) Uani d . 1 . .
N N2 0.3774(3) 0.4754(7) 0.6981(3) 0.0226(10) Uani d . 1 . .
N N3 0.4867(3) 0.6892(7) 0.7112(3) 0.0276(11) Uani d . 1 . .
H H31 0.5135 0.6021 0.6932 0.033 Uiso calc R 1 . .
H H32 0.5107 0.8029 0.7242 0.033 Uiso calc R 1 . .
N N4 0.3299(3) 0.4781(7) 0.8970(3) 0.0276(11) Uani d . 1 . .
N N6 0.2340(3) 0.7942(6) 0.8656(3) 0.0186(9) Uani d . 1 . .
C C1 0.1130(4) 0.3300(8) 0.7005(3) 0.0198(11) Uani d . 1 . .
C C2 0.0305(3) 0.2459(8) 0.6918(3) 0.0192(11) Uani d . 1 . .
H H2A -0.0049 0.3053 0.7170 0.023 Uiso calc R 1 . .
C C3 -0.0009(4) 0.0790(8) 0.6476(3) 0.0199(11) Uani d . 1 . .
C C4 0.0493(4) -0.0115(8) 0.6105(3) 0.0250(12) Uani d . 1 . .
H H4 0.0276 -0.1248 0.5798 0.030 Uiso calc R 1 . .
C C5 0.1305(4) 0.0642(8) 0.6187(3) 0.0246(12) Uani d . 1 . .
H H5 0.1644 0.0017 0.5927 0.030 Uiso calc R 1 . .
C C6 0.1660(3) 0.2315(7) 0.6641(3) 0.0182(10) Uani d . 1 . .
C C7 0.2514(4) 0.2930(8) 0.6672(3) 0.0210(11) Uani d . 1 . .
H H7 0.2788 0.2180 0.6388 0.025 Uiso calc R 1 . .
C C8 0.4083(4) 0.6481(8) 0.7189(3) 0.0233(12) Uani d . 1 . .
C C9 0.3807(6) 0.3222(11) 0.9082(5) 0.0486(19) Uani d U 1 . .
H H9 0.3852 0.2632 0.8615 0.058 Uiso calc R 1 . .
C C10 0.4268(7) 0.2446(14) 0.9857(5) 0.068(3) Uani d U 1 . .
H H10 0.4631 0.1346 0.9924 0.082 Uiso calc R 1 . .
C C11 0.4195(6) 0.3282(13) 1.0529(5) 0.059(2) Uani d U 1 . .
H H11 0.4503 0.2752 1.1065 0.071 Uiso calc R 1 . .
C C12 0.3680(5) 0.4878(11) 1.0429(4) 0.0390(16) Uani d U 1 . .
H H12 0.3628 0.5480 1.0890 0.047 Uiso calc R 1 . .
C C13 0.3235(4) 0.5594(9) 0.9635(3) 0.0246(12) Uani d . 1 . .
C C14 0.2655(4) 0.7348(8) 0.9444(3) 0.0235(12) Uani d . 1 . .
C C15 0.2450(5) 0.8306(10) 1.0037(4) 0.0345(15) Uani d . 1 . .
H H15 0.2672 0.7861 1.0592 0.041 Uiso calc R 1 . .
C C16 0.1917(5) 0.9915(11) 0.9804(4) 0.0429(18) Uani d . 1 . .
H H16 0.1754 1.0573 1.0194 0.051 Uiso calc R 1 . .
C C17 0.1624(5) 1.0556(9) 0.9000(4) 0.0356(15) Uani d . 1 . .
H H17 0.1276 1.1684 0.8831 0.043 Uiso calc R 1 . .
C C18 0.1848(4) 0.9525(8) 0.8448(4) 0.0242(12) Uani d . 1 . .
H H18 0.1643 0.9961 0.7893 0.029 Uiso calc R 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'
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'
S S 0.1246 0.1234 '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 N1 . . 90.29(16) ?
O1 Zn1 N4 . . 102.37(18) ?
N1 Zn1 N4 . . 100.70(19) ?
O1 Zn1 N6 . . 93.82(16) ?
N1 Zn1 N6 . . 175.77(18) ?
N4 Zn1 N6 . . 77.46(19) ?
O1 Zn1 S1 . . 146.42(12) ?
N1 Zn1 S1 . . 81.14(13) ?
N4 Zn1 S1 . . 111.10(15) ?
N6 Zn1 S1 . . 95.92(13) ?
C8 S1 Zn1 . . 92.73(19) ?
C1 O1 Zn1 . . 128.1(3) ?
C3 O2 H2 . . 109.5 ?
C7 N1 N2 . . 114.5(5) ?
C7 N1 Zn1 . . 125.7(4) ?
N2 N1 Zn1 . . 119.5(3) ?
C8 N2 N1 . . 112.9(5) ?
C8 N3 H31 . . 120.0 ?
C8 N3 H32 . . 120.0 ?
H31 N3 H32 . . 120.0 ?
C9 N4 C13 . . 118.5(5) ?
C9 N4 Zn1 . . 124.9(5) ?
C13 N4 Zn1 . . 116.5(4) ?
C18 N6 C14 . . 118.9(5) ?
C18 N6 Zn1 . . 125.2(4) ?
C14 N6 Zn1 . . 115.8(4) ?
O1 C1 C2 . . 119.8(5) ?
O1 C1 C6 . . 123.2(5) ?
C2 C1 C6 . . 117.0(5) ?
C3 C2 C1 . . 122.2(5) ?
C3 C2 H2A . . 118.9 ?
C1 C2 H2A . . 118.9 ?
O2 C3 C4 . . 117.3(5) ?
O2 C3 C2 . . 122.4(5) ?
C4 C3 C2 . . 120.3(5) ?
C5 C4 C3 . . 119.2(5) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 122.6(5) ?
C4 C5 H5 . . 118.7 ?
C6 C5 H5 . . 118.7 ?
C5 C6 C7 . . 116.2(5) ?
C5 C6 C1 . . 118.6(5) ?
C7 C6 C1 . . 125.1(5) ?
N1 C7 C6 . . 125.5(5) ?
N1 C7 H7 . . 117.2 ?
C6 C7 H7 . . 117.2 ?
N2 C8 N3 . . 115.8(5) ?
N2 C8 S1 . . 126.5(4) ?
N3 C8 S1 . . 117.6(4) ?
N4 C9 C10 . . 121.7(7) ?
N4 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
C11 C10 C9 . . 119.2(7) ?
C11 C10 H10 . . 120.4 ?
C9 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.0(7) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C13 . . 118.1(7) ?
C11 C12 H12 . . 121.0 ?
C13 C12 H12 . . 121.0 ?
N4 C13 C12 . . 122.4(6) ?
N4 C13 C14 . . 114.3(5) ?
C12 C13 C14 . . 123.2(6) ?
N6 C14 C15 . . 121.5(6) ?
N6 C14 C13 . . 115.6(5) ?
C15 C14 C13 . . 122.9(5) ?
C16 C15 C14 . . 118.7(6) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C17 C16 C15 . . 119.3(6) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C18 C17 C16 . . 118.5(6) ?
C18 C17 H17 . . 120.8 ?
C16 C17 H17 . . 120.8 ?
N6 C18 C17 . . 123.0(5) ?
N6 C18 H18 . . 118.5 ?
C17 C18 H18 . . 118.5 ?
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 . 1.983(4) ?
Zn1 N1 . 2.045(5) ?
Zn1 N4 . 2.109(5) ?
Zn1 N6 . 2.112(5) ?
Zn1 S1 . 2.3911(15) ?
S1 C8 . 1.746(6) ?
O1 C1 . 1.329(7) ?
O2 C3 . 1.354(6) ?
O2 H2 . 0.8400 ?
N1 C7 . 1.306(7) ?
N1 N2 . 1.403(6) ?
N2 C8 . 1.310(7) ?
N3 C8 . 1.355(7) ?
N3 H31 . 0.8800 ?
N3 H32 . 0.8800 ?
N4 C9 . 1.338(8) ?
N4 C13 . 1.346(8) ?
N6 C18 . 1.333(7) ?
N6 C14 . 1.340(7) ?
C1 C2 . 1.408(7) ?
C1 C6 . 1.437(7) ?
C2 C3 . 1.389(8) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.385(8) ?
C4 C5 . 1.367(8) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.412(8) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.423(7) ?
C7 H7 . 0.9500 ?
C9 C10 . 1.381(10) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.370(12) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.367(10) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.387(8) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.505(8) ?
C14 C15 . 1.393(8) ?
C15 C16 . 1.382(10) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.380(9) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.373(9) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
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
O2 H2 O1 2_546 0.84 1.85 2.625(5) 153 yes
N3 H32 N2 2_656 0.88 2.15 2.936(7) 148 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 Zn1 S1 C8 . . . . -95.8(3) ?
N1 Zn1 S1 C8 . . . . -18.8(2) ?
N4 Zn1 S1 C8 . . . . 79.3(2) ?
N6 Zn1 S1 C8 . . . . 158.1(2) ?
N1 Zn1 O1 C1 . . . . 15.3(4) ?
N4 Zn1 O1 C1 . . . . -85.8(4) ?
N6 Zn1 O1 C1 . . . . -163.8(4) ?
S1 Zn1 O1 C1 . . . . 89.5(5) ?
O1 Zn1 N1 C7 . . . . -13.1(5) ?
N4 Zn1 N1 C7 . . . . 89.5(5) ?
S1 Zn1 N1 C7 . . . . -160.5(5) ?
O1 Zn1 N1 N2 . . . . 173.2(4) ?
N4 Zn1 N1 N2 . . . . -84.1(4) ?
S1 Zn1 N1 N2 . . . . 25.8(4) ?
C7 N1 N2 C8 . . . . 163.9(5) ?
Zn1 N1 N2 C8 . . . . -21.8(6) ?
O1 Zn1 N4 C9 . . . . 92.1(6) ?
N1 Zn1 N4 C9 . . . . -0.5(6) ?
N6 Zn1 N4 C9 . . . . -176.7(6) ?
S1 Zn1 N4 C9 . . . . -85.1(6) ?
O1 Zn1 N4 C13 . . . . -89.4(4) ?
N1 Zn1 N4 C13 . . . . 177.9(4) ?
N6 Zn1 N4 C13 . . . . 1.8(4) ?
S1 Zn1 N4 C13 . . . . 93.4(4) ?
O1 Zn1 N6 C18 . . . . -78.4(4) ?
N4 Zn1 N6 C18 . . . . 179.8(5) ?
S1 Zn1 N6 C18 . . . . 69.4(4) ?
O1 Zn1 N6 C14 . . . . 97.3(4) ?
N4 Zn1 N6 C14 . . . . -4.6(4) ?
S1 Zn1 N6 C14 . . . . -114.9(4) ?
Zn1 O1 C1 C2 . . . . 167.2(4) ?
Zn1 O1 C1 C6 . . . . -11.3(7) ?
O1 C1 C2 C3 . . . . 179.0(5) ?
C6 C1 C2 C3 . . . . -2.4(8) ?
C1 C2 C3 O2 . . . . -179.6(5) ?
C1 C2 C3 C4 . . . . 0.3(8) ?
O2 C3 C4 C5 . . . . -179.3(5) ?
C2 C3 C4 C5 . . . . 0.7(8) ?
C3 C4 C5 C6 . . . . 0.4(9) ?
C4 C5 C6 C7 . . . . 179.9(5) ?
C4 C5 C6 C1 . . . . -2.5(8) ?
O1 C1 C6 C5 . . . . -178.1(5) ?
C2 C1 C6 C5 . . . . 3.3(7) ?
O1 C1 C6 C7 . . . . -0.7(8) ?
C2 C1 C6 C7 . . . . -179.2(5) ?
N2 N1 C7 C6 . . . . -178.8(5) ?
Zn1 N1 C7 C6 . . . . 7.3(8) ?
C5 C6 C7 N1 . . . . 180.0(5) ?
C1 C6 C7 N1 . . . . 2.5(9) ?
N1 N2 C8 N3 . . . . -178.7(5) ?
N1 N2 C8 S1 . . . . -1.0(7) ?
Zn1 S1 C8 N2 . . . . 17.3(5) ?
Zn1 S1 C8 N3 . . . . -165.0(4) ?
C13 N4 C9 C10 . . . . -0.5(12) ?
Zn1 N4 C9 C10 . . . . 178.0(7) ?
N4 C9 C10 C11 . . . . 0.7(15) ?
C9 C10 C11 C12 . . . . -0.8(16) ?
C10 C11 C12 C13 . . . . 0.6(13) ?
C9 N4 C13 C12 . . . . 0.3(10) ?
Zn1 N4 C13 C12 . . . . -178.3(5) ?
C9 N4 C13 C14 . . . . 179.5(6) ?
Zn1 N4 C13 C14 . . . . 0.9(6) ?
C11 C12 C13 N4 . . . . -0.4(10) ?
C11 C12 C13 C14 . . . . -179.5(7) ?
C18 N6 C14 C15 . . . . 2.6(8) ?
Zn1 N6 C14 C15 . . . . -173.4(5) ?
C18 N6 C14 C13 . . . . -177.6(5) ?
Zn1 N6 C14 C13 . . . . 6.4(6) ?
N4 C13 C14 N6 . . . . -4.9(7) ?
C12 C13 C14 N6 . . . . 174.3(6) ?
N4 C13 C14 C15 . . . . 174.9(6) ?
C12 C13 C14 C15 . . . . -5.9(9) ?
N6 C14 C15 C16 . . . . -0.7(10) ?
C13 C14 C15 C16 . . . . 179.5(6) ?
C14 C15 C16 C17 . . . . -1.7(11) ?
C15 C16 C17 C18 . . . . 2.3(11) ?
C14 N6 C18 C17 . . . . -2.0(9) ?
Zn1 N6 C18 C17 . . . . 173.5(5) ?
C16 C17 C18 N6 . . . . -0.5(10) ?
