#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217555.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_2217555
loop_
_publ_author_name
'Yurii S. Moroz'
'Tetyana Yu. Sliva'
'Kinga Kulon'
'Henryk Kozłowski'
'Igor O. Fritsky'
_publ_section_title
;Dichlorido{2-hydroxyimino-N'-[1-(2-pyridyl)ethylidene]propanohydrazide-κ³N,N',O}zinc(II)
 hemihydrate
;
_journal_coeditor_code           HY2108
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m353
_journal_page_last               m354
_journal_paper_doi               10.1107/S160053680706535X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Zn Cl2 (C10 H12 N4 O2)], 0.5H2 O'
_chemical_formula_moiety         'C10 H13 Cl2 N4 O2.50 Zn'
_chemical_formula_sum            'C10 H13 Cl2 N4 O2.5 Zn'
_chemical_formula_weight         365.51
_chemical_name_systematic
;
Dichlorido[2-hydroxyimino-N'-[1-(2-pyridyl)ethylidene]propanohydrazide-
κ³N,N',O]zinc(II) monohydrate
;
_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                 109.873(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5666(8)
_cell_length_b                   12.9898(8)
_cell_length_c                   15.8671(8)
_cell_measurement_reflns_used    3373
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      3.06
_cell_volume                     2823.5(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'KM-4 CCD Software (Kuma, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Kum KM4 CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17382
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(PLATON; Spek, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+3.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                3069
_reflns_number_total             3373
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            hy2108.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C10 H13 Cl2 N4 O2.50 Zn'
_cod_database_code               2217555
_cod_database_fobs_code          2217555
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_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
C C1 0.8446(2) 0.45584(19) 0.90460(16) 0.0300(6) Uani d . 1
H H1A 0.8849 0.3958 0.9225 0.045 Uiso calc R 1
H H1B 0.8500 0.4827 0.8501 0.045 Uiso calc R 1
H H1C 0.7778 0.4378 0.8949 0.045 Uiso calc R 1
C C2 0.87720(17) 0.53560(17) 0.97658(14) 0.0155(4) Uani d . 1
C C3 0.86291(17) 0.64543(17) 0.95017(14) 0.0149(4) Uani d . 1
C C4 0.89866(16) 0.89516(17) 1.03894(14) 0.0127(4) Uani d . 1
C C5 0.96032(18) 0.89213(18) 1.13564(14) 0.0187(5) Uani d . 1
H H5A 0.9937 0.8272 1.1490 0.028 Uiso calc R 1
H H5B 0.9197 0.9003 1.1718 0.028 Uiso calc R 1
H H5C 1.0073 0.9469 1.1483 0.028 Uiso calc R 1
C C6 0.86661(16) 0.99579(17) 0.99301(14) 0.0124(4) Uani d . 1
C C7 0.89136(17) 1.08943(18) 1.03628(15) 0.0163(5) Uani d . 1
H H7 0.9293 1.0921 1.0967 0.020 Uiso calc R 1
C C8 0.85855(19) 1.17985(18) 0.98807(16) 0.0194(5) Uani d . 1
H H8 0.8745 1.2437 1.0157 0.023 Uiso calc R 1
C C9 0.80194(19) 1.17314(18) 0.89857(16) 0.0203(5) Uani d . 1
H H9 0.7788 1.2323 0.8650 0.024 Uiso calc R 1
C C10 0.78027(17) 1.07659(18) 0.85973(15) 0.0181(5) Uani d . 1
H H10 0.7424 1.0722 0.7994 0.022 Uiso calc R 1
N N1 0.81153(14) 0.98950(15) 0.90538(12) 0.0140(4) Uani d . 1
N N2 0.86837(14) 0.81687(14) 0.98712(12) 0.0127(4) Uani d . 1
N N3 0.88998(14) 0.71758(14) 1.01651(13) 0.0144(4) Uani d . 1
N N4 0.91703(14) 0.51964(14) 1.06044(12) 0.0161(4) Uani d . 1
O O1 0.82753(14) 0.67055(12) 0.87067(10) 0.0213(4) Uani d . 1
O O2 0.92836(13) 0.41557(13) 1.08008(11) 0.0211(4) Uani d . 1
Cl Cl2 0.88241(4) 0.85938(4) 0.75864(3) 0.01726(13) Uani d . 1
Cl Cl3 0.63307(4) 0.81753(5) 0.78506(4) 0.01874(13) Uani d . 1
Zn Zn1 0.793127(19) 0.838156(19) 0.848619(16) 0.01239(8) Uani d . 1
H H1 0.954(3) 0.413(3) 1.139(2) 0.048(10) Uiso d . 1
O O1W 0.0000 0.34448(19) 0.2500 0.0206(5) Uani d S 1
H H1W 0.045(2) 0.308(3) 0.250(2) 0.048(11) Uiso d . 1
H H2 0.905(2) 0.699(2) 1.068(2) 0.024(8) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
N4 C2 C3 115.0(2) ?
N4 C2 C1 126.8(2) ?
C3 C2 C1 118.27(19) ?
O1 C3 N3 121.2(2) ?
O1 C3 C2 120.9(2) ?
N3 C3 C2 117.88(19) ?
N2 C4 C5 126.3(2) ?
N2 C4 C6 113.42(18) ?
C5 C4 C6 120.29(19) ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
N1 C6 C7 121.8(2) ?
N1 C6 C4 115.30(19) ?
C7 C6 C4 122.86(19) ?
C6 C7 C8 119.1(2) ?
C6 C7 H7 120.5 ?
C8 C7 H7 120.5 ?
C9 C8 C7 119.0(2) ?
C9 C8 H8 120.5 ?
C7 C8 H8 120.5 ?
C8 C9 C10 118.7(2) ?
C8 C9 H9 120.6 ?
C10 C9 H9 120.6 ?
N1 C10 C9 122.7(2) ?
N1 C10 H10 118.6 ?
C9 C10 H10 118.6 ?
C10 N1 C6 118.69(19) ?
C10 N1 Zn1 125.33(15) ?
C6 N1 Zn1 115.73(15) ?
C4 N2 N3 122.44(18) ?
C4 N2 Zn1 120.30(15) ?
N3 N2 Zn1 117.03(13) ?
C3 N3 N2 114.28(18) ?
C3 N3 H2 119(2) ?
N2 N3 H2 125(2) ?
C2 N4 O2 111.77(18) ?
C3 O1 Zn1 114.29(14) ?
N4 O2 H1 104(2) ?
N2 Zn1 N1 74.71(7) yes
N2 Zn1 Cl3 123.36(5) ?
N1 Zn1 Cl3 105.30(5) ?
N2 Zn1 O1 72.57(6) yes
N1 Zn1 O1 147.07(6) ?
Cl3 Zn1 O1 95.66(5) ?
N2 Zn1 Cl2 117.91(5) ?
N1 Zn1 Cl2 97.91(5) ?
Cl3 Zn1 Cl2 118.08(2) ?
O1 Zn1 Cl2 94.10(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.495(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 N4 1.275(3) ?
C2 C3 1.482(3) ?
C3 O1 1.233(3) ?
C3 N3 1.364(3) ?
C4 N2 1.288(3) ?
C4 C5 1.492(3) ?
C4 C6 1.492(3) ?
C5 H5A 0.9600 ?
C5 H5B 0.9600 ?
C5 H5C 0.9600 ?
C6 N1 1.351(3) ?
C6 C7 1.383(3) ?
C7 C8 1.394(3) ?
C7 H7 0.9300 ?
C8 C9 1.381(3) ?
C8 H8 0.9300 ?
C9 C10 1.386(3) ?
C9 H9 0.9300 ?
C10 N1 1.337(3) ?
C10 H10 0.9300 ?
Zn1 N1 2.1409(19) y
N2 N3 1.371(3) ?
Zn1 N2 2.1142(18) y
N3 H2 0.80(3) ?
N4 O2 1.384(2) ?
Zn1 O1 2.2348(16) y
O2 H1 0.88(3) ?
Zn1 Cl2 2.2513(6) y
Zn1 Cl3 2.2195(6) y
O1W H1W 0.81(3) ?
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
N3 H2 Cl3 7_667 0.80(3) 2.59(3) 3.310(2) 150(3) y
O1W H1W Cl2 5_666 0.81(3) 2.44(3) 3.182(2) 153(3) y
O2 H1 O1W 1_656 0.88(3) 1.89(4) 2.7015(19) 153(3) y
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
N4 C2 C3 O1 178.0(2)
C1 C2 C3 O1 -2.0(4)
N4 C2 C3 N3 -2.1(3)
C1 C2 C3 N3 177.9(2)
N2 C4 C6 N1 0.0(3)
C5 C4 C6 N1 179.6(2)
N2 C4 C6 C7 -179.8(2)
C5 C4 C6 C7 -0.1(3)
N1 C6 C7 C8 0.0(3)
C4 C6 C7 C8 179.7(2)
C6 C7 C8 C9 0.3(4)
C7 C8 C9 C10 -0.4(4)
C8 C9 C10 N1 0.3(4)
C9 C10 N1 C6 -0.1(3)
C9 C10 N1 Zn1 -173.99(18)
C7 C6 N1 C10 -0.1(3)
C4 C6 N1 C10 -179.9(2)
C7 C6 N1 Zn1 174.42(17)
C4 C6 N1 Zn1 -5.4(2)
C5 C4 N2 N3 0.4(3)
C6 C4 N2 N3 179.97(19)
C5 C4 N2 Zn1 -173.95(18)
C6 C4 N2 Zn1 5.7(3)
O1 C3 N3 N2 4.1(3)
C2 C3 N3 N2 -175.80(19)
C4 N2 N3 C3 -171.8(2)
Zn1 N2 N3 C3 2.7(2)
C3 C2 N4 O2 -179.79(19)
C1 C2 N4 O2 0.2(4)
N3 C3 O1 Zn1 -8.3(3)
C2 C3 O1 Zn1 171.56(16)
C4 N2 Zn1 N1 -6.55(17)
N3 N2 Zn1 N1 178.85(17)
C4 N2 Zn1 Cl3 -105.03(17)
N3 N2 Zn1 Cl3 80.36(16)
C4 N2 Zn1 O1 169.73(19)
N3 N2 Zn1 O1 -4.88(15)
C4 N2 Zn1 Cl2 84.41(17)
N3 N2 Zn1 Cl2 -90.20(15)
C10 N1 Zn1 N2 -179.8(2)
C6 N1 Zn1 N2 6.09(15)
C10 N1 Zn1 Cl3 -58.74(19)
C6 N1 Zn1 Cl3 127.17(14)
C10 N1 Zn1 O1 173.63(16)
C6 N1 Zn1 O1 -0.5(2)
C10 N1 Zn1 Cl2 63.31(19)
C6 N1 Zn1 Cl2 -110.78(15)
C3 O1 Zn1 N2 6.96(17)
C3 O1 Zn1 N1 13.6(2)
C3 O1 Zn1 Cl3 -116.27(17)
C3 O1 Zn1 Cl2 124.96(17)
