#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236576.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_2236576
loop_
_publ_author_name
'Song, Lianqing'
'Zhao, Meihong'
'Cui, Guoshi'
'Gao, Jianghua'
'Lin, Lin'
_publ_section_title
;
 Dichloridobis{1-[(2-methylbenzimidazol-1-yl-κN³)methyl]benzotriazole}zinc
;
_journal_coeditor_code           RK2368
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1179
_journal_paper_doi               10.1107/S160053681203526X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Zn Cl2 (C15 H13 N5)2]'
_chemical_formula_moiety         'C30 H26 Cl2 N10 Zn'
_chemical_formula_sum            'C30 H26 Cl2 N10 Zn'
_chemical_formula_weight         662.90
_chemical_name_systematic
;
Dichloridobis{1-[(2-methylbenzimidazol-1-yl-
κN³)methyl]benzotriazole}zinc
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.721(4)
_cell_length_b                   12.617(4)
_cell_length_c                   14.728(3)
_cell_measurement_reflns_used    3926
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.8565
_cell_measurement_theta_min      2.0780
_cell_volume                     2884.3(13)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17560
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.8133
_exptl_absorpt_correction_T_min  0.7974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2006)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0504
_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)+(0.0749P)²+0.7625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                2977
_reflns_number_total             3423
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2368.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236576
_cod_database_fobs_code          2236576
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
_atom_site_symmetry_multiplicity
Zn Zn1 0.0000 0.58999(3) 0.2500 0.04555(17) Uani d S 1 2
N N1 0.02430(13) 0.48160(16) 0.15242(14) 0.0412(5) Uani d . 1 1
N N2 0.08873(13) 0.35668(17) 0.08201(15) 0.0421(5) Uani d . 1 1
N N3 0.14451(15) 0.18031(19) 0.08324(15) 0.0489(5) Uani d . 1 1
N N4 0.14628(19) 0.1031(2) 0.01911(17) 0.0623(7) Uani d . 1 1
N N5 0.13466(19) 0.0122(2) 0.05545(18) 0.0653(7) Uani d . 1 1
C C1 -0.03854(16) 0.42678(18) 0.09166(16) 0.0379(5) Uani d . 1 1
C C2 -0.12745(17) 0.4407(2) 0.07150(18) 0.0472(6) Uani d . 1 1
H H2 -0.1550 0.4934 0.1000 0.057 Uiso calc R 1 1
C C3 -0.17295(18) 0.3735(3) 0.0079(2) 0.0525(7) Uani d . 1 1
H H3 -0.2325 0.3805 -0.0062 0.063 Uiso calc R 1 1
C C4 -0.13169(19) 0.2953(2) -0.0360(2) 0.0567(7) Uani d . 1 1
H H4 -0.1646 0.2515 -0.0787 0.068 Uiso calc R 1 1
C C5 -0.04384(19) 0.2807(2) -0.01797(18) 0.0493(6) Uani d . 1 1
H H5 -0.0163 0.2288 -0.0475 0.059 Uiso calc R 1 1
C C6 0.00111(16) 0.34824(19) 0.04711(16) 0.0387(5) Uani d . 1 1
C C7 0.09879(16) 0.4373(2) 0.14406(17) 0.0417(6) Uani d . 1 1
C C8 0.18438(18) 0.4695(3) 0.1936(2) 0.0620(8) Uani d . 1 1
H H8A 0.1787 0.5340 0.2268 0.093 Uiso calc R 1 1
H H8B 0.2230 0.4808 0.1502 0.093 Uiso calc R 1 1
H H8C 0.2068 0.4147 0.2360 0.093 Uiso calc R 1 1
C C9 0.15636(18) 0.2894(2) 0.0572(2) 0.0509(7) Uani d . 1 1
H H9A 0.1560 0.2934 -0.0086 0.061 Uiso calc R 1 1
H H9B 0.2119 0.3146 0.0878 0.061 Uiso calc R 1 1
C C10 0.13101(16) 0.1366(2) 0.16454(17) 0.0454(6) Uani d . 1 1
C C11 0.1241(2) 0.1776(3) 0.25161(19) 0.0562(7) Uani d . 1 1
H H11 0.1292 0.2497 0.2644 0.067 Uiso calc R 1 1
C C12 0.1096(2) 0.1053(3) 0.3164(2) 0.0637(9) Uani d . 1 1
H H12 0.1046 0.1293 0.3750 0.076 Uiso calc R 1 1
C C13 0.10205(19) -0.0044(3) 0.2980(2) 0.0668(9) Uani d . 1 1
H H13 0.0923 -0.0508 0.3444 0.080 Uiso calc R 1 1
C C14 0.1089(2) -0.0433(3) 0.2129(2) 0.0633(8) Uani d . 1 1
H H14 0.1034 -0.1154 0.2002 0.076 Uiso calc R 1 1
C C15 0.12426(18) 0.0289(2) 0.14573(19) 0.0512(7) Uani d . 1 1
Cl Cl1 -0.11365(6) 0.69095(6) 0.19298(5) 0.0643(3) Uani d . 1 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'
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'
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
N1 Zn1 N1 2 . 96.95(12)
N1 Zn1 Cl1 2 2 109.86(6)
N1 Zn1 Cl1 . 2 114.34(6)
N1 Zn1 Cl1 2 . 114.34(6)
N1 Zn1 Cl1 . . 109.86(6)
Cl1 Zn1 Cl1 2 . 110.89(5)
C7 N1 C1 . . 106.0(2)
C7 N1 Zn1 . . 127.62(17)
C1 N1 Zn1 . . 125.50(16)
C7 N2 C6 . . 107.9(2)
C7 N2 C9 . . 126.5(2)
C6 N2 C9 . . 125.6(2)
N4 N3 C10 . . 110.1(2)
N4 N3 C9 . . 118.6(2)
C10 N3 C9 . . 131.3(2)
N5 N4 N3 . . 109.2(2)
N4 N5 C15 . . 108.1(2)
C6 C1 C2 . . 119.9(2)
C6 C1 N1 . . 109.2(2)
C2 C1 N1 . . 130.8(2)
C3 C2 C1 . . 117.6(3)
C3 C2 H2 . . 121.2
C1 C2 H2 . . 121.2
C2 C3 C4 . . 121.4(3)
C2 C3 H3 . . 119.3
C4 C3 H3 . . 119.3
C5 C4 C3 . . 122.1(3)
C5 C4 H4 . . 119.0
C3 C4 H4 . . 119.0
C4 C5 C6 . . 115.8(3)
C4 C5 H5 . . 122.1
C6 C5 H5 . . 122.1
C5 C6 C1 . . 123.1(2)
C5 C6 N2 . . 131.7(2)
C1 C6 N2 . . 105.2(2)
N1 C7 N2 . . 111.7(2)
N1 C7 C8 . . 125.9(2)
N2 C7 C8 . . 122.4(2)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
N3 C9 N2 . . 111.0(2)
N3 C9 H9A . . 109.4
N2 C9 H9A . . 109.4
N3 C9 H9B . . 109.4
N2 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
N3 C10 C15 . . 103.8(2)
N3 C10 C11 . . 134.3(3)
C15 C10 C11 . . 121.9(3)
C12 C11 C10 . . 116.0(3)
C12 C11 H11 . . 122.0
C10 C11 H11 . . 122.0
C11 C12 C13 . . 122.7(3)
C11 C12 H12 . . 118.7
C13 C12 H12 . . 118.7
C14 C13 C12 . . 120.7(3)
C14 C13 H13 . . 119.6
C12 C13 H13 . . 119.6
C13 C14 C15 . . 117.7(3)
C13 C14 H14 . . 121.2
C15 C14 H14 . . 121.2
N5 C15 C10 . . 108.9(2)
N5 C15 C14 . . 130.1(3)
C10 C15 C14 . . 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 N1 2 2.063(2)
Zn1 N1 . 2.063(2)
Zn1 Cl1 2 2.2458(9)
Zn1 Cl1 . 2.2458(9)
N1 C7 . 1.321(3)
N1 C1 . 1.405(3)
N2 C7 . 1.359(3)
N2 C6 . 1.396(3)
N2 C9 . 1.451(3)
N3 N4 . 1.360(3)
N3 C10 . 1.365(3)
N3 C9 . 1.449(3)
N4 N5 . 1.290(4)
N5 C15 . 1.381(4)
C1 C6 . 1.390(3)
C1 C2 . 1.393(4)
C2 C3 . 1.376(4)
C2 H2 . 0.9300
C3 C4 . 1.395(4)
C3 H3 . 0.9300
C4 C5 . 1.377(4)
C4 H4 . 0.9300
C5 C6 . 1.389(3)
C5 H5 . 0.9300
C7 C8 . 1.482(4)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C15 . 1.388(4)
C10 C11 . 1.403(4)
C11 C12 . 1.366(4)
C11 H11 . 0.9300
C12 C13 . 1.412(5)
C12 H12 . 0.9300
C13 C14 . 1.366(5)
C13 H13 . 0.9300
C14 C15 . 1.395(4)
C14 H14 . 0.9300
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
N1 Zn1 N1 C7 2 -88.2(2)
Cl1 Zn1 N1 C7 2 27.3(2)
Cl1 Zn1 N1 C7 . 152.8(2)
N1 Zn1 N1 C1 2 79.87(19)
Cl1 Zn1 N1 C1 2 -164.61(17)
Cl1 Zn1 N1 C1 . -39.2(2)
C10 N3 N4 N5 . -0.1(3)
C9 N3 N4 N5 . 180.0(3)
N3 N4 N5 C15 . 0.4(4)
C7 N1 C1 C6 . 0.1(3)
Zn1 N1 C1 C6 . -170.04(15)
C7 N1 C1 C2 . -179.1(3)
Zn1 N1 C1 C2 . 10.7(4)
C6 C1 C2 C3 . 0.9(4)
N1 C1 C2 C3 . -179.9(3)
C1 C2 C3 C4 . -0.9(4)
C2 C3 C4 C5 . 0.2(5)
C3 C4 C5 C6 . 0.5(4)
C4 C5 C6 C1 . -0.5(4)
C4 C5 C6 N2 . -179.9(3)
C2 C1 C6 C5 . -0.2(4)
N1 C1 C6 C5 . -179.5(2)
C2 C1 C6 N2 . 179.4(2)
N1 C1 C6 N2 . 0.0(3)
C7 N2 C6 C5 . 179.3(3)
C9 N2 C6 C5 . -1.8(4)
C7 N2 C6 C1 . -0.1(3)
C9 N2 C6 C1 . 178.7(2)
C1 N1 C7 N2 . -0.2(3)
Zn1 N1 C7 N2 . 169.67(16)
C1 N1 C7 C8 . 178.9(3)
Zn1 N1 C7 C8 . -11.2(4)
C6 N2 C7 N1 . 0.2(3)
C9 N2 C7 N1 . -178.6(2)
C6 N2 C7 C8 . -179.0(3)
C9 N2 C7 C8 . 2.2(4)
N4 N3 C9 N2 . 129.2(3)
C10 N3 C9 N2 . -50.8(4)
C7 N2 C9 N3 . 115.7(3)
C6 N2 C9 N3 . -62.9(3)
N4 N3 C10 C15 . -0.3(3)
C9 N3 C10 C15 . 179.7(3)
N4 N3 C10 C11 . 179.5(3)
C9 N3 C10 C11 . -0.6(5)
N3 C10 C11 C12 . 179.7(3)
C15 C10 C11 C12 . -0.6(4)
C10 C11 C12 C13 . 0.1(4)
C11 C12 C13 C14 . -0.2(5)
C12 C13 C14 C15 . 0.6(4)
N4 N5 C15 C10 . -0.6(3)
N4 N5 C15 C14 . 179.0(3)
N3 C10 C15 N5 . 0.6(3)
C11 C10 C15 N5 . -179.3(3)
N3 C10 C15 C14 . -179.1(3)
C11 C10 C15 C14 . 1.1(4)
C13 C14 C15 N5 . 179.4(3)
C13 C14 C15 C10 . -1.0(4)
