#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/77/1517705.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_1517705
loop_
_publ_author_name
'Bozidar Cobeljic'
'Andrej Pevec'
'Iztok Turel'
'Marcel Swart'
'Dragana Mitic'
'Marina Milenkovic'
'Ivanka Markovic'
'Maja Jovanovic'
'Dusan Sladic'
'Marko Jeremic'
'Katarina Andelkovic'
_publ_section_title
;
 Synthesis, characterization, DFT calculations and biological activity of
 derivatives of 3-acetylpyridine and the zinc(II) complex with the
 condensation product of 3-acetylpyridine and semicarbazide
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              5
_journal_page_last               12
_journal_volume                  404
_journal_year                    2013
_chemical_formula_sum            'C16 H20 Cl2 N8 O2 Zn'
_chemical_formula_weight         492.67
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.43810(10)
_cell_length_b                   11.6257(2)
_cell_length_c                   23.9731(5)
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2073.03(6)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'φ scans + 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4402
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    1.473
_exptl_absorpt_correction_T_max  0.8667
_exptl_absorpt_correction_T_min  0.7571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+0.8938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                1827
_reflns_number_total             2378
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ICA-2013-404-5-12-1.cif
_cod_data_source_block           k2212
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               1517705
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
Zn1 Zn 0.0000 0.36953(3) 0.2500 0.03426(12) Uani 1 2 d S
Cl1 Cl 0.18450(8) 0.47114(5) 0.30428(3) 0.05644(19) Uani 1 1 d .
N1 N 0.1659(2) 0.27138(14) 0.20067(7) 0.0366(4) Uani 1 1 d .
N2 N 0.3064(2) -0.03340(14) 0.07983(7) 0.0374(4) Uani 1 1 d .
N3 N 0.2811(2) -0.12410(14) 0.04439(8) 0.0393(4) Uani 1 1 d D
H3N H 0.177(2) -0.1513(19) 0.0344(10) 0.047 Uiso 1 1 d D
N4 N 0.5859(3) -0.1530(2) 0.05172(10) 0.0568(6) Uani 1 1 d D
H4NA H 0.681(3) -0.182(2) 0.0385(11) 0.068 Uiso 1 1 d D
H4NB H 0.585(4) -0.103(2) 0.0775(10) 0.068 Uiso 1 1 d D
O1 O 0.41956(19) -0.26169(13) -0.00665(6) 0.0453(4) Uani 1 1 d .
C1 C 0.1145(3) 0.18189(17) 0.16830(8) 0.0363(4) Uani 1 1 d .
H1 H -0.0041 0.1569 0.1703 0.044 Uiso 1 1 calc R
C2 C 0.2304(3) 0.12610(16) 0.13243(8) 0.0331(4) Uani 1 1 d .
C3 C 0.4081(3) 0.16482(19) 0.13045(9) 0.0409(5) Uani 1 1 d .
H3 H 0.4903 0.1295 0.1068 0.049 Uiso 1 1 calc R
C4 C 0.4609(3) 0.2549(2) 0.16347(10) 0.0456(5) Uani 1 1 d .
H4 H 0.5793 0.2807 0.1629 0.055 Uiso 1 1 calc R
C5 C 0.3364(3) 0.30636(18) 0.19733(9) 0.0421(5) Uani 1 1 d .
H5 H 0.3723 0.3686 0.2190 0.051 Uiso 1 1 calc R
C6 C 0.1740(3) 0.02822(16) 0.09632(8) 0.0336(4) Uani 1 1 d .
C7 C -0.0188(3) 0.01249(19) 0.08144(9) 0.0405(5) Uani 1 1 d .
H7A H -0.0286 -0.0415 0.0513 0.061 Uiso 1 1 calc R
H7B H -0.0689 0.0850 0.0702 0.061 Uiso 1 1 calc R
H7C H -0.0832 -0.0162 0.1132 0.061 Uiso 1 1 calc R
C8 C 0.4320(3) -0.18341(18) 0.02809(9) 0.0383(5) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Zn1 N1 112.55(9) . 4
N1 Zn1 Cl1 105.09(5) . .
N1 Zn1 Cl1 109.14(5) 4 .
N1 Zn1 Cl1 109.14(5) . 4
N1 Zn1 Cl1 105.09(5) 4 4
Cl1 Zn1 Cl1 116.02(4) . 4
C5 N1 C1 117.96(18) . .
C5 N1 Zn1 115.86(14) . .
C1 N1 Zn1 125.94(14) . .
C6 N2 N3 121.19(17) . .
N2 N3 C8 116.83(17) . .
N2 N3 H3N 125.1(16) . .
C8 N3 H3N 117.7(15) . .
C8 N4 H4NA 117.1(19) . .
C8 N4 H4NB 119(2) . .
H4NA N4 H4NB 124(3) . .
N1 C1 C2 122.83(19) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
C1 C2 C3 117.44(18) . .
C1 C2 C6 123.06(18) . .
C3 C2 C6 119.51(18) . .
C4 C3 C2 119.9(2) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 118.8(2) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
N1 C5 C4 123.1(2) . .
N1 C5 H5 118.5 . .
C4 C5 H5 118.5 . .
N2 C6 C7 126.72(18) . .
N2 C6 C2 112.99(17) . .
C7 C6 C2 120.25(17) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O1 C8 N4 123.3(2) . .
O1 C8 N3 119.95(19) . .
N4 C8 N3 116.74(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.0552(16) .
Zn1 N1 2.0552(16) 4
Zn1 Cl1 2.2298(6) .
Zn1 Cl1 2.2298(6) 4
N1 C5 1.334(3) .
N1 C1 1.353(2) .
N2 C6 1.280(3) .
N2 N3 1.367(2) .
N3 C8 1.374(3) .
N3 H3N 0.868(16) .
N4 C8 1.325(3) .
N4 H4NA 0.841(16) .
N4 H4NB 0.850(17) .
O1 C8 1.237(2) .
C1 C2 1.380(3) .
C1 H1 0.9300 .
C2 C3 1.397(3) .
C2 C6 1.490(3) .
C3 C4 1.371(3) .
C3 H3 0.9300 .
C4 C5 1.369(3) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.489(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
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
N1 Zn1 N1 C5 -136.96(17) 4
Cl1 Zn1 N1 C5 -18.30(16) .
Cl1 Zn1 N1 C5 106.77(15) 4
N1 Zn1 N1 C1 48.87(15) 4
Cl1 Zn1 N1 C1 167.54(15) .
Cl1 Zn1 N1 C1 -67.39(16) 4
C6 N2 N3 C8 178.57(19) .
C5 N1 C1 C2 0.1(3) .
Zn1 N1 C1 C2 174.11(15) .
N1 C1 C2 C3 0.4(3) .
N1 C1 C2 C6 -179.43(18) .
C1 C2 C3 C4 0.1(3) .
C6 C2 C3 C4 179.9(2) .
C2 C3 C4 C5 -0.9(3) .
C1 N1 C5 C4 -1.0(3) .
Zn1 N1 C5 C4 -175.66(18) .
C3 C4 C5 N1 1.4(4) .
N3 N2 C6 C7 0.8(3) .
N3 N2 C6 C2 -177.17(17) .
C1 C2 C6 N2 -159.59(19) .
C3 C2 C6 N2 20.6(3) .
C1 C2 C6 C7 22.3(3) .
C3 C2 C6 C7 -157.49(19) .
N2 N3 C8 O1 -175.44(19) .
N2 N3 C8 N4 5.3(3) .
