#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/11/2211161.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_2211161
loop_
_publ_author_name
'Xie, Xue-Qun'
'Yang, Chun-Long'
'Li, Qian-Jin'
'Luo, Jin-Xiang'
_publ_section_title
Dichlorobis(1-{[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl}-1H-1,2,4-triazole-κN⁴)zinc(II)
_journal_coeditor_code           OB3027
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3096
_journal_page_last               m3097
_journal_paper_doi               10.1107/S1600536806042723
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Zn Cl2 (C12 H11 Cl2 N3 O2)2]'
_chemical_formula_moiety         'C24 H22 Cl6 N6 O4 Zn'
_chemical_formula_sum            'C24 H22 Cl6 N6 O4 Zn'
_chemical_formula_weight         736.55
_chemical_melting_point          459
_chemical_name_systematic
;
Dichlorobis{1-[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-
1H-1,2,4-triazole-\kN⁴}zinc(II)
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.958(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.662(4)
_cell_length_b                   5.5801(13)
_cell_length_c                   16.295(4)
_cell_measurement_reflns_used    1793
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.51
_cell_volume                     1470.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3983
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    1.424
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.606
_refine_ls_abs_structure_details 'Flack (1983), 1145 Friedel pairs'
_refine_ls_abs_structure_Flack   0.037(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0480
_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)+(0.0608P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2461
_reflns_number_total             2745
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob3027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2211161
_cod_database_fobs_code          2211161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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 0.2572(3) 1.0299(8) 0.2971(3) 0.0360(11) Uani d . 1
C C2 0.1887(3) 1.1696(9) 0.2950(3) 0.0396(11) Uani d . 1
C C3 0.1386(3) 1.1313(13) 0.3504(3) 0.0516(13) Uani d . 1
H H3 0.0929 1.2285 0.3486 0.062 Uiso calc R 1
C C4 0.1570(3) 0.9524(12) 0.4066(3) 0.0539(15) Uani d . 1
C C5 0.2238(4) 0.8069(12) 0.4123(3) 0.0604(16) Uani d . 1
H H5 0.2357 0.6844 0.4521 0.073 Uiso calc R 1
C C6 0.2734(3) 0.8483(11) 0.3566(3) 0.0535(14) Uani d . 1
H H6 0.3191 0.7505 0.3593 0.064 Uiso calc R 1
C C7 0.3117(3) 1.0501(8) 0.2345(3) 0.0362(11) Uani d . 1
C C8 0.2656(3) 0.9419(10) 0.1503(3) 0.0420(11) Uani d . 1
H H8A 0.2458 0.7835 0.1601 0.050 Uiso calc R 1
H H8B 0.2179 1.0406 0.1258 0.050 Uiso calc R 1
C C9 0.3676(3) 0.7487(9) 0.0837(3) 0.0381(11) Uani d . 1
H H9 0.3740 0.6079 0.1151 0.046 Uiso calc R 1
C C10 0.3773(3) 1.0162(9) -0.0015(3) 0.0427(12) Uani d . 1
H H10 0.3942 1.1002 -0.0436 0.051 Uiso calc R 1
C C11 0.4503(3) 1.0826(11) 0.2890(3) 0.0519(12) Uani d . 1
H H11A 0.4880 1.0722 0.2522 0.062 Uiso calc R 1
H H11B 0.4809 1.0503 0.3466 0.062 Uiso calc R 1
C C12 0.4114(3) 1.3230(11) 0.2830(3) 0.0498(13) Uani d . 1
H H12A 0.4025 1.3735 0.3371 0.060 Uiso calc R 1
H H12B 0.4449 1.4418 0.2633 0.060 Uiso calc R 1
Cl Cl1 0.15906(8) 1.4006(3) 0.22328(8) 0.0563(4) Uani d . 1
Cl Cl2 0.09348(10) 0.9034(5) 0.47553(10) 0.0921(7) Uani d . 1
Cl Cl3 0.53721(7) 0.3978(2) 0.12156(7) 0.0476(3) Uani d . 1
N N1 0.3180(2) 0.9241(7) 0.0911(2) 0.0362(8) Uani d . 1
N N2 0.3225(2) 1.1004(9) 0.0360(2) 0.0439(8) Uani d . 1
N N3 0.4072(2) 0.8009(7) 0.0250(2) 0.0367(9) Uani d . 1
O O1 0.3848(2) 0.9181(6) 0.2637(2) 0.0453(8) Uani d . 1
O O2 0.3356(2) 1.2854(6) 0.22318(19) 0.0409(8) Uani d . 1
Zn Zn1 0.5000 0.60209(12) 0.0000 0.0388(2) Uani d S 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
_geom_angle_publ_flag
C2 C1 C6 . . 116.8(4) ?
C2 C1 C7 . . 124.5(4) ?
C6 C1 C7 . . 118.5(4) ?
C1 C2 C3 . . 121.6(5) ?
C1 C2 Cl1 . . 122.6(4) ?
C3 C2 Cl1 . . 115.8(4) ?
C4 C3 C2 . . 119.1(5) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 122.6(5) ?
C3 C4 Cl2 . . 119.0(4) ?
C5 C4 Cl2 . . 118.4(5) ?
C4 C5 C6 . . 117.5(5) ?
C4 C5 H5 . . 121.2 ?
C6 C5 H5 . . 121.2 ?
C1 C6 C5 . . 122.4(5) ?
C1 C6 H6 . . 118.8 ?
C5 C6 H6 . . 118.8 ?
O2 C7 O1 . . 106.6(4) ?
O2 C7 C1 . . 113.1(3) ?
O1 C7 C1 . . 110.0(3) ?
O2 C7 C8 . . 110.6(4) ?
O1 C7 C8 . . 107.7(4) ?
C1 C7 C8 . . 108.7(4) ?
N1 C8 C7 . . 111.8(4) ?
N1 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
N1 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
N1 C9 N3 . . 109.9(4) ?
N1 C9 H9 . . 125.0 ?
N3 C9 H9 . . 125.0 ?
N2 C10 N3 . . 115.1(4) ?
N2 C10 H10 . . 122.5 ?
N3 C10 H10 . . 122.5 ?
O1 C11 C12 . . 105.9(4) ?
O1 C11 H11A . . 110.6 ?
C12 C11 H11A . . 110.6 ?
O1 C11 H11B . . 110.6 ?
C12 C11 H11B . . 110.6 ?
H11A C11 H11B . . 108.7 ?
O2 C12 C11 . . 102.4(4) ?
O2 C12 H12A . . 111.3 ?
C11 C12 H12A . . 111.3 ?
O2 C12 H12B . . 111.3 ?
C11 C12 H12B . . 111.3 ?
H12A C12 H12B . . 109.2 ?
C9 N1 N2 . . 110.3(4) ?
C9 N1 C8 . . 127.5(4) ?
N2 N1 C8 . . 122.2(4) ?
C10 N2 N1 . . 102.0(4) ?
C9 N3 C10 . . 102.7(4) ?
C9 N3 Zn1 . . 124.5(3) ?
C10 N3 Zn1 . . 132.4(3) ?
C7 O1 C11 . . 107.8(4) ?
C7 O2 C12 . . 106.5(4) ?
N3 Zn1 N3 2_655 . 113.5(2) yes
N3 Zn1 Cl3 2_655 2_655 99.38(11) ?
N3 Zn1 Cl3 . 2_655 113.28(11) yes
N3 Zn1 Cl3 2_655 . 113.28(11) ?
N3 Zn1 Cl3 . . 99.38(11) yes
Cl3 Zn1 Cl3 2_655 . 118.80(8) yes
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
C1 C2 . 1.376(6) ?
C1 C6 . 1.383(7) ?
C1 C7 . 1.524(6) ?
C2 C3 . 1.386(6) ?
C2 Cl1 . 1.730(5) ?
C3 C4 . 1.339(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.363(8) ?
C4 Cl2 . 1.741(5) ?
C5 C6 . 1.385(7) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O2 . 1.398(6) ?
C7 O1 . 1.404(5) ?
C7 C8 . 1.526(6) ?
C8 N1 . 1.451(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N1 . 1.305(6) ?
C9 N3 . 1.320(6) ?
C9 H9 . 0.9300 ?
C10 N2 . 1.301(6) ?
C10 N3 . 1.332(6) ?
C10 H10 . 0.9300 ?
C11 O1 . 1.410(6) ?
C11 C12 . 1.483(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O2 . 1.412(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
Zn1 Cl3 . 2.2394(13) yes
N1 N2 . 1.347(6) ?
Zn1 N3 . 2.023(4) ?
Zn1 N3 2_655 2.023(4) yes
Zn1 Cl3 2_655 2.2394(13) ?
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
C8 H8A Cl1 1_545 0.97 2.90 3.835(5) 161.3 yes
C9 H9 O2 1_545 0.93 2.70 3.566(6) 155.3 yes
C10 H10 Cl3 2_665 0.93 2.52 3.426(5) 163.3 yes
