#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/32/2213246.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_2213246
loop_
_publ_author_name
'Maroszová, Jaroslava'
'Findoráková, Lenka'
'Györyvá, Katarína'
'Moncol, Jan'
'Melník, Milan'
_publ_section_title
;
 Bis(2-chlorobenzoato-κ²O,O')bis[methyl
 N-(3-pyridyl)carbamato-κN]zinc(II)
;
_journal_coeditor_code           CI2367
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1520
_journal_page_last               m1520
_journal_paper_doi               10.1107/S1600536807019836
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Zn (C7 H4 Cl O2)2 (C7 H8 N2 O2)2]'
_chemical_formula_moiety         'C28 H24 Cl2 N4 O8 Zn'
_chemical_formula_sum            'C28 H24 Cl2 N4 O8 Zn'
_chemical_formula_weight         680.78
_chemical_name_systematic
;
Bis(2-chlorobenzoato-κ²O,O')bis[methyl
N-(3-pyridyl)carbamato-κN]zinc(II)
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.444(3)
_cell_length_b                   13.650(3)
_cell_length_c                   13.627(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      8.61
_cell_measurement_theta_min      4.52
_cell_volume                     2872.7(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            4275
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        4.3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.339
_exptl_absorpt_correction_T_min  0.304
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XEMP; Siemens, 1994)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.9964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                2566
_reflns_number_total             3429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2367.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2872.7(10)
_cod_database_code               2213246
_cod_database_fobs_code          2213246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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
Zn Zn 0.2500 0.2500 0.00830(3) 0.04173(11) Uani d S 1
Cl Cl 0.02319(4) 0.17755(6) -0.27367(6) 0.0697(2) Uani d . 1
N N1 0.30551(11) 0.34776(13) 0.10944(13) 0.0420(4) Uani d . 1
N N2 0.22484(13) 0.47062(13) 0.32673(15) 0.0503(5) Uani d . 1
H H2 0.1861 0.4281 0.3423 0.060 Uiso calc R 1
O O1 0.14614(11) 0.33727(13) -0.02481(14) 0.0577(4) Uani d . 1
O O2 0.14705(12) 0.20595(14) -0.11392(15) 0.0677(5) Uani d . 1
O O3 0.27541(12) 0.62242(13) 0.36654(14) 0.0632(5) Uani d . 1
O O4 0.15579(14) 0.55887(13) 0.43625(14) 0.0683(5) Uani d . 1
C C1 0.11059(14) 0.28121(17) -0.08633(17) 0.0458(5) Uani d . 1
C C2 0.02036(13) 0.30729(14) -0.11921(16) 0.0402(4) Uani d . 1
C C3 -0.02401(14) 0.26336(16) -0.19616(17) 0.0450(5) Uani d . 1
C C4 -0.10918(16) 0.2880(2) -0.21635(19) 0.0567(6) Uani d . 1
H H4 -0.1382 0.2570 -0.2675 0.068 Uiso calc R 1
C C5 -0.15084(17) 0.3575(2) -0.1616(2) 0.0647(7) Uani d . 1
H H5 -0.2082 0.3732 -0.1752 0.078 Uiso calc R 1
C C6 -0.10790(17) 0.4042(2) -0.0863(2) 0.0643(7) Uani d . 1
H H6 -0.1356 0.4525 -0.0499 0.077 Uiso calc R 1
C C7 -0.02320(15) 0.37853(18) -0.06538(18) 0.0519(5) Uani d . 1
H H7 0.0053 0.4097 -0.0140 0.062 Uiso calc R 1
C C8 0.25616(14) 0.37803(15) 0.18363(16) 0.0423(4) Uani d . 1
H H8 0.2005 0.3525 0.1891 0.051 Uiso calc R 1
C C9 0.28322(14) 0.44532(15) 0.25299(15) 0.0411(4) Uani d . 1
C C10 0.36653(15) 0.48203(17) 0.24529(17) 0.0494(5) Uani d . 1
H H10 0.3877 0.5266 0.2910 0.059 Uiso calc R 1
C C11 0.41724(15) 0.45099(18) 0.16834(19) 0.0539(6) Uani d . 1
H H11 0.4732 0.4751 0.1612 0.065 Uiso calc R 1
C C12 0.38551(14) 0.38477(18) 0.10245(17) 0.0502(5) Uani d . 1
H H12 0.4207 0.3647 0.0509 0.060 Uiso calc R 1
C C13 0.22424(16) 0.55699(17) 0.37586(17) 0.0492(5) Uani d . 1
C C14 0.1445(2) 0.6486(2) 0.4903(2) 0.0798(9) Uani d . 1
H H14A 0.1280 0.7000 0.4461 0.120 Uiso calc R 1
H H14B 0.1979 0.6656 0.5220 0.120 Uiso calc R 1
H H14C 0.1001 0.6398 0.5388 0.120 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'
Zn Zn 0.2839 1.4301 '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'
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
O1 Zn O1 . 2 154.55(11)
O1 Zn N1 . . 95.43(7)
O1 Zn N1 2 . 101.20(7)
O1 Zn N1 . 2 101.20(7)
O1 Zn N1 2 2 95.43(7)
N1 Zn N1 . 2 98.02(10)
O1 Zn O2 . . 57.97(6)
O1 Zn O2 2 . 102.83(7)
N1 Zn O2 . . 153.14(6)
N1 Zn O2 2 . 91.49(7)
O1 Zn O2 . 2 102.83(7)
O1 Zn O2 2 2 57.97(6)
N1 Zn O2 . 2 91.49(7)
N1 Zn O2 2 2 153.14(6)
O2 Zn O2 . 2 91.17(10)
O1 Zn C1 . 2 130.40(8)
O1 Zn C1 2 2 29.39(7)
N1 Zn C1 . 2 95.36(7)
N1 Zn C1 2 2 124.83(7)
O2 Zn C1 . 2 99.69(7)
O2 Zn C1 2 2 28.68(7)
C8 N1 C12 . . 117.73(19)
C8 N1 Zn . . 117.48(14)
C12 N1 Zn . . 124.73(15)
C13 N2 C9 . . 125.2(2)
C13 N2 H2 . . 117.4
C9 N2 H2 . . 117.4
C1 O1 Zn . . 97.73(14)
C1 O2 Zn . . 83.16(15)
C13 O4 C14 . . 115.2(2)
O2 C1 O1 . . 120.7(2)
O2 C1 C2 . . 122.0(2)
O1 C1 C2 . . 117.2(2)
C3 C2 C7 . . 117.46(19)
C3 C2 C1 . . 125.4(2)
C7 C2 C1 . . 117.1(2)
C4 C3 C2 . . 120.9(2)
C4 C3 Cl . . 116.18(19)
C2 C3 Cl . . 122.89(17)
C5 C4 C3 . . 120.4(2)
C5 C4 H4 . . 119.8
C3 C4 H4 . . 119.8
C4 C5 C6 . . 120.0(2)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C5 C6 C7 . . 119.4(3)
C5 C6 H6 . . 120.3
C7 C6 H6 . . 120.3
C6 C7 C2 . . 121.7(2)
C6 C7 H7 . . 119.2
C2 C7 H7 . . 119.2
N1 C8 C9 . . 123.51(19)
N1 C8 H8 . . 118.2
C9 C8 H8 . . 118.2
C8 C9 C10 . . 118.0(2)
C8 C9 N2 . . 117.5(2)
C10 C9 N2 . . 124.5(2)
C11 C10 C9 . . 118.4(2)
C11 C10 H10 . . 120.8
C9 C10 H10 . . 120.8
C12 C11 C10 . . 120.1(2)
C12 C11 H11 . . 120.0
C10 C11 H11 . . 120.0
N1 C12 C11 . . 122.3(2)
N1 C12 H12 . . 118.8
C11 C12 H12 . . 118.8
O3 C13 O4 . . 124.8(2)
O3 C13 N2 . . 126.2(2)
O4 C13 N2 . . 109.0(2)
O4 C14 H14A . . 109.5
O4 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
O4 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn O1 . 2.0484(16)
Zn O1 2 2.0484(16)
Zn N1 . 2.1012(18)
Zn N1 2 2.1012(18)
Zn O2 . 2.380(2)
Zn O2 2 2.380(2)
Zn C1 2 2.546(2)
Cl C3 . 1.737(2)
N1 C8 . 1.332(3)
N1 C12 . 1.338(3)
N2 C13 . 1.356(3)
N2 C9 . 1.394(3)
N2 H2 . 0.86
O1 C1 . 1.261(3)
O2 C1 . 1.230(3)
O3 C13 . 1.199(3)
O4 C13 . 1.340(3)
O4 C14 . 1.439(3)
C1 C2 . 1.506(3)
C2 C3 . 1.389(3)
C2 C7 . 1.391(3)
C3 C4 . 1.385(3)
C4 C5 . 1.368(4)
C4 H4 . 0.93
C5 C6 . 1.378(4)
C5 H5 . 0.93
C6 C7 . 1.384(3)
C6 H6 . 0.93
C7 H7 . 0.93
C8 C9 . 1.383(3)
C8 H8 . 0.93
C9 C10 . 1.385(3)
C10 C11 . 1.376(3)
C10 H10 . 0.93
C11 C12 . 1.365(3)
C11 H11 . 0.93
C12 H12 . 0.93
C14 H14A . 0.96
C14 H14B . 0.96
C14 H14C . 0.96
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
N2 H2 O2 8_566 0.86 2.02 2.812(3) 153
C8 H8 Cl 8_566 0.93 2.82 3.723(2) 165
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
O1 Zn N1 C8 . 55.12(16)
O1 Zn N1 C8 2 -144.24(15)
N1 Zn N1 C8 2 -47.03(13)
O2 Zn N1 C8 . 62.6(2)
O2 Zn N1 C8 2 158.16(15)
C1 Zn N1 C8 2 -173.37(15)
O1 Zn N1 C12 . -122.03(18)
O1 Zn N1 C12 2 38.62(19)
N1 Zn N1 C12 2 135.8(2)
O2 Zn N1 C12 . -114.5(2)
O2 Zn N1 C12 2 -18.99(18)
C1 Zn N1 C12 2 9.49(19)
O1 Zn O1 C1 2 48.91(13)
N1 Zn O1 C1 . 179.75(14)
N1 Zn O1 C1 2 -80.94(15)
O2 Zn O1 C1 . 3.74(13)
O2 Zn O1 C1 2 86.97(15)
C1 Zn O1 C1 2 77.97(19)
O1 Zn O2 C1 . -3.83(13)
O1 Zn O2 C1 2 -165.62(14)
N1 Zn O2 C1 . -12.6(2)
N1 Zn O2 C1 2 98.47(15)
O2 Zn O2 C1 2 -108.26(15)
C1 Zn O2 C1 2 -135.80(13)
Zn O2 C1 O1 . 6.1(2)
Zn O2 C1 C2 . -170.09(19)
Zn O1 C1 O2 . -7.2(2)
Zn O1 C1 C2 . 169.25(16)
O2 C1 C2 C3 . -13.6(3)
O1 C1 C2 C3 . 170.0(2)
O2 C1 C2 C7 . 163.7(2)
O1 C1 C2 C7 . -12.7(3)
C7 C2 C3 C4 . -1.8(3)
C1 C2 C3 C4 . 175.5(2)
C7 C2 C3 Cl . 176.85(17)
C1 C2 C3 Cl . -5.9(3)
C2 C3 C4 C5 . 1.1(3)
Cl C3 C4 C5 . -177.63(19)
C3 C4 C5 C6 . 0.6(4)
C4 C5 C6 C7 . -1.5(4)
C5 C6 C7 C2 . 0.7(4)
C3 C2 C7 C6 . 0.9(3)
C1 C2 C7 C6 . -176.6(2)
C12 N1 C8 C9 . 0.1(3)
Zn N1 C8 C9 . -177.22(16)
N1 C8 C9 C10 . -0.9(3)
N1 C8 C9 N2 . 179.92(19)
C13 N2 C9 C8 . -153.2(2)
C13 N2 C9 C10 . 27.6(4)
C8 C9 C10 C11 . 1.1(3)
N2 C9 C10 C11 . -179.7(2)
C9 C10 C11 C12 . -0.7(4)
C8 N1 C12 C11 . 0.3(3)
Zn N1 C12 C11 . 177.46(18)
C10 C11 C12 N1 . 0.0(4)
C14 O4 C13 O3 . 1.7(4)
C14 O4 C13 N2 . -177.3(2)
C9 N2 C13 O3 . -3.4(4)
C9 N2 C13 O4 . 175.6(2)
