# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_aa

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?

_chemical_name_common            
'dicholoride 1,2-di(1H-benzo[d]imidazol-2-yl)benzene Zinc(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Cl2 N4 Zn, C3 H7 N O, H2 O'
_chemical_formula_sum            'C23 H23 Cl2 N5 O2 Zn'
_chemical_formula_weight         537.73

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.374(2)
_cell_length_b                   10.3710(16)
_cell_length_c                   18.186(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.074(3)
_cell_angle_gamma                90.00
_cell_volume                     2320.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    1.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5819
_exptl_absorpt_correction_T_max  0.7971
_exptl_absorpt_process_details   'SADABS (Bruker, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9873
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4055
_reflns_number_gt                3184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.8496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.22768(2) 0.80039(3) 0.095929(16) 0.01923(10) Uani 1 1 d . . .
N1 N 0.19192(17) 0.6233(2) 0.13176(12) 0.0194(5) Uani 1 1 d . . .
C1 C 0.1659(2) 0.5884(3) 0.20215(14) 0.0208(6) Uani 1 1 d . . .
C2 C 0.1570(2) 0.6637(3) 0.26508(15) 0.0270(7) Uani 1 1 d . . .
H2 H 0.1723 0.7534 0.2655 0.032 Uiso 1 1 calc R . .
C3 C 0.1254(3) 0.6025(3) 0.32607(16) 0.0343(8) Uani 1 1 d . . .
H3 H 0.1203 0.6509 0.3699 0.041 Uiso 1 1 calc R . .
C4 C 0.1001(2) 0.4703(3) 0.32579(16) 0.0344(8) Uani 1 1 d . . .
H4 H 0.0777 0.4318 0.3691 0.041 Uiso 1 1 calc R . .
C5 C 0.1075(2) 0.3953(3) 0.26367(16) 0.0313(7) Uani 1 1 d . . .
H5 H 0.0906 0.3059 0.2630 0.038 Uiso 1 1 calc R . .
C6 C 0.1411(2) 0.4580(3) 0.20203(15) 0.0220(6) Uani 1 1 d . . .
N2 N 0.15262(18) 0.4150(2) 0.13169(12) 0.0220(5) Uani 1 1 d . . .
H2A H 0.1428 0.3353 0.1157 0.026 Uiso 1 1 calc R . .
C7 C 0.1817(2) 0.5166(2) 0.09129(14) 0.0182(6) Uani 1 1 d . . .
C8 C 0.1831(2) 0.5038(2) 0.01025(14) 0.0185(6) Uani 1 1 d . . .
C9 C 0.1057(2) 0.4204(3) -0.02455(15) 0.0221(6) Uani 1 1 d . . .
H9 H 0.0597 0.3742 0.0048 0.027 Uiso 1 1 calc R . .
C10 C 0.0935(2) 0.4026(3) -0.10023(15) 0.0251(6) Uani 1 1 d . . .
H10 H 0.0411 0.3433 -0.1220 0.030 Uiso 1 1 calc R . .
C11 C 0.1573(2) 0.4711(3) -0.14399(15) 0.0280(7) Uani 1 1 d . . .
H11 H 0.1473 0.4623 -0.1963 0.034 Uiso 1 1 calc R . .
C12 C 0.2363(2) 0.5529(3) -0.11069(15) 0.0231(6) Uani 1 1 d . . .
H12 H 0.2812 0.5988 -0.1410 0.028 Uiso 1 1 calc R . .
C13 C 0.2525(2) 0.5706(2) -0.03419(14) 0.0197(6) Uani 1 1 d . . .
C14 C 0.3473(2) 0.6515(3) -0.00788(14) 0.0190(6) Uani 1 1 d . . .
N3 N 0.44213(18) 0.6375(2) -0.03735(12) 0.0211(5) Uani 1 1 d . . .
H3A H 0.4559 0.5795 -0.0704 0.025 Uiso 1 1 calc R . .
C15 C 0.5139(2) 0.7294(3) -0.00685(14) 0.0214(6) Uani 1 1 d . . .
C16 C 0.6216(2) 0.7566(3) -0.01668(15) 0.0270(7) Uani 1 1 d . . .
H16 H 0.6600 0.7080 -0.0497 0.032 Uiso 1 1 calc R . .
C17 C 0.6697(2) 0.8574(3) 0.02383(17) 0.0323(7) Uani 1 1 d . . .
H17 H 0.7430 0.8795 0.0184 0.039 Uiso 1 1 calc R . .
C18 C 0.6124(2) 0.9281(3) 0.07302(16) 0.0328(7) Uani 1 1 d . . .
H18 H 0.6483 0.9965 0.1005 0.039 Uiso 1 1 calc R . .
C19 C 0.5053(2) 0.9015(3) 0.08276(16) 0.0284(7) Uani 1 1 d . . .
H19 H 0.4671 0.9503 0.1158 0.034 Uiso 1 1 calc R . .
C20 C 0.4562(2) 0.7998(3) 0.04188(14) 0.0204(6) Uani 1 1 d . . .
N4 N 0.35175(17) 0.7486(2) 0.03992(12) 0.0198(5) Uani 1 1 d . . .
Cl1 Cl 0.27687(6) 0.94358(7) 0.18609(4) 0.02883(18) Uani 1 1 d . . .
Cl2 Cl 0.08291(6) 0.86395(7) 0.02149(4) 0.03029(18) Uani 1 1 d . . .
C21 C 0.5562(2) 0.6156(3) 0.17105(15) 0.0271(7) Uani 1 1 d . . .
H21 H 0.6191 0.6357 0.1476 0.032 Uiso 1 1 calc R . .
O1 O 0.49727(17) 0.52875(19) 0.14331(11) 0.0304(5) Uani 1 1 d . . .
N5 N 0.53995(19) 0.6833(2) 0.23030(12) 0.0247(5) Uani 1 1 d . . .
C22 C 0.6189(3) 0.7769(3) 0.26129(19) 0.0431(9) Uani 1 1 d . . .
H22A H 0.6564 0.7432 0.3075 0.065 Uiso 1 1 calc R . .
H22B H 0.5817 0.8575 0.2714 0.065 Uiso 1 1 calc R . .
H22C H 0.6719 0.7935 0.2260 0.065 Uiso 1 1 calc R . .
C23 C 0.4459(3) 0.6628(3) 0.26961(17) 0.0350(8) Uani 1 1 d . . .
H23A H 0.4007 0.5944 0.2452 0.053 Uiso 1 1 calc R . .
H23B H 0.4036 0.7427 0.2696 0.053 Uiso 1 1 calc R . .
H23C H 0.4695 0.6373 0.3207 0.053 Uiso 1 1 calc R . .
O2 O 0.12973(19) 0.1613(2) 0.09916(13) 0.0424(6) Uani 1 1 d . . .
H202 H 0.0747 0.1342 0.0713 0.076(15) Uiso 1 1 d R . .
H201 H 0.1624 0.0985 0.1217 0.049(11) Uiso 1 1 d R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N4 2.003(2) . ?
Zn1 N1 2.013(2) . ?
Zn1 Cl2 2.2278(8) . ?
Zn1 Cl1 2.2479(8) . ?
N1 C7 1.327(3) . ?
N1 C1 1.400(3) . ?
C1 C6 1.387(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9500 . ?
C6 N2 1.376(3) . ?
N2 C7 1.355(3) . ?
N2 H2A 0.8800 . ?
C7 C8 1.482(3) . ?
C8 C9 1.392(4) . ?
C8 C13 1.420(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.480(4) . ?
C14 N4 1.328(3) . ?
C14 N3 1.349(3) . ?
N3 C15 1.379(3) . ?
N3 H3A 0.8800 . ?
C15 C16 1.392(4) . ?
C15 C20 1.400(4) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 N4 1.394(3) . ?
C21 O1 1.233(3) . ?
C21 N5 1.319(3) . ?
C21 H21 0.9500 . ?
N5 C23 1.445(4) . ?
N5 C22 1.448(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O2 H202 0.8523 . ?
O2 H201 0.8479 . ?

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
_geom_angle_publ_flag
N4 Zn1 N1 97.28(9) . . ?
N4 Zn1 Cl2 112.37(7) . . ?
N1 Zn1 Cl2 106.05(7) . . ?
N4 Zn1 Cl1 112.64(7) . . ?
N1 Zn1 Cl1 114.73(6) . . ?
Cl2 Zn1 Cl1 112.71(3) . . ?
C7 N1 C1 105.9(2) . . ?
C7 N1 Zn1 126.31(17) . . ?
C1 N1 Zn1 127.70(17) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 N1 108.9(2) . . ?
C2 C1 N1 130.4(3) . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
N2 C6 C1 105.8(2) . . ?
N2 C6 C5 131.6(3) . . ?
C1 C6 C5 122.5(3) . . ?
C7 N2 C6 108.2(2) . . ?
C7 N2 H2A 125.9 . . ?
C6 N2 H2A 125.9 . . ?
N1 C7 N2 111.3(2) . . ?
N1 C7 C8 128.0(2) . . ?
N2 C7 C8 120.1(2) . . ?
C9 C8 C13 118.2(2) . . ?
C9 C8 C7 115.3(2) . . ?
C13 C8 C7 126.5(2) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 122.4(3) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C8 118.2(2) . . ?
C12 C13 C14 114.9(2) . . ?
C8 C13 C14 126.8(2) . . ?
N4 C14 N3 111.3(2) . . ?
N4 C14 C13 128.2(2) . . ?
N3 C14 C13 120.2(2) . . ?
C14 N3 C15 108.4(2) . . ?
C14 N3 H3A 125.8 . . ?
C15 N3 H3A 125.8 . . ?
N3 C15 C16 132.3(3) . . ?
N3 C15 C20 105.4(2) . . ?
C16 C15 C20 122.3(3) . . ?
C17 C16 C15 116.8(3) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 116.9(3) . . ?
C18 C19 H19 121.5 . . ?
C20 C19 H19 121.5 . . ?
C19 C20 N4 130.8(3) . . ?
C19 C20 C15 120.6(3) . . ?
N4 C20 C15 108.6(2) . . ?
C14 N4 C20 106.2(2) . . ?
C14 N4 Zn1 123.70(18) . . ?
C20 N4 Zn1 130.05(18) . . ?
O1 C21 N5 126.1(3) . . ?
O1 C21 H21 117.0 . . ?
N5 C21 H21 117.0 . . ?
C21 N5 C23 121.7(2) . . ?
C21 N5 C22 121.3(3) . . ?
C23 N5 C22 116.9(2) . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 H23A 109.5 . . ?
N5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H202 O2 H201 110.2 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Zn1 N1 C7 -46.8(2) . . . . ?
Cl2 Zn1 N1 C7 69.0(2) . . . . ?
Cl1 Zn1 N1 C7 -165.92(19) . . . . ?
N4 Zn1 N1 C1 137.7(2) . . . . ?
Cl2 Zn1 N1 C1 -106.4(2) . . . . ?
Cl1 Zn1 N1 C1 18.7(2) . . . . ?
C7 N1 C1 C6 0.6(3) . . . . ?
Zn1 N1 C1 C6 176.72(18) . . . . ?
C7 N1 C1 C2 -175.8(3) . . . . ?
Zn1 N1 C1 C2 0.4(4) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
N1 C1 C2 C3 177.3(3) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 N2 176.9(2) . . . . ?
N1 C1 C6 N2 0.2(3) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
N1 C1 C6 C5 -177.4(2) . . . . ?
C4 C5 C6 N2 -176.9(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C1 C6 N2 C7 -0.9(3) . . . . ?
C5 C6 N2 C7 176.4(3) . . . . ?
C1 N1 C7 N2 -1.1(3) . . . . ?
Zn1 N1 C7 N2 -177.36(17) . . . . ?
C1 N1 C7 C8 169.7(2) . . . . ?
Zn1 N1 C7 C8 -6.5(4) . . . . ?
C6 N2 C7 N1 1.3(3) . . . . ?
C6 N2 C7 C8 -170.4(2) . . . . ?
N1 C7 C8 C9 -137.8(3) . . . . ?
N2 C7 C8 C9 32.4(3) . . . . ?
N1 C7 C8 C13 40.1(4) . . . . ?
N2 C7 C8 C13 -149.7(3) . . . . ?
C13 C8 C9 C10 -1.1(4) . . . . ?
C7 C8 C9 C10 177.0(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C9 C10 C11 C12 2.8(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 C8 -1.5(4) . . . . ?
C11 C12 C13 C14 174.3(3) . . . . ?
C9 C8 C13 C12 2.6(4) . . . . ?
C7 C8 C13 C12 -175.3(2) . . . . ?
C9 C8 C13 C14 -172.7(2) . . . . ?
C7 C8 C13 C14 9.5(4) . . . . ?
C12 C13 C14 N4 132.6(3) . . . . ?
C8 C13 C14 N4 -52.0(4) . . . . ?
C12 C13 C14 N3 -41.9(3) . . . . ?
C8 C13 C14 N3 133.5(3) . . . . ?
N4 C14 N3 C15 0.7(3) . . . . ?
C13 C14 N3 C15 176.1(2) . . . . ?
C14 N3 C15 C16 179.0(3) . . . . ?
C14 N3 C15 C20 -0.5(3) . . . . ?
N3 C15 C16 C17 -179.7(3) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 N4 179.1(3) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
N3 C15 C20 C19 179.8(2) . . . . ?
C16 C15 C20 C19 0.2(4) . . . . ?
N3 C15 C20 N4 0.2(3) . . . . ?
C16 C15 C20 N4 -179.3(2) . . . . ?
N3 C14 N4 C20 -0.5(3) . . . . ?
C13 C14 N4 C20 -175.4(3) . . . . ?
N3 C14 N4 Zn1 -179.71(16) . . . . ?
C13 C14 N4 Zn1 5.4(4) . . . . ?
C19 C20 N4 C14 -179.4(3) . . . . ?
C15 C20 N4 C14 0.2(3) . . . . ?
C19 C20 N4 Zn1 -0.2(4) . . . . ?
C15 C20 N4 Zn1 179.28(18) . . . . ?
N1 Zn1 N4 C14 48.6(2) . . . . ?
Cl2 Zn1 N4 C14 -62.1(2) . . . . ?
Cl1 Zn1 N4 C14 169.28(19) . . . . ?
N1 Zn1 N4 C20 -130.4(2) . . . . ?
Cl2 Zn1 N4 C20 118.9(2) . . . . ?
Cl1 Zn1 N4 C20 -9.7(2) . . . . ?
O1 C21 N5 C23 -1.2(5) . . . . ?
O1 C21 N5 C22 175.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.88 1.83 2.705(3) 170.0 .
N3 H3A O1 0.88 1.87 2.748(3) 171.6 3_665
O2 H202 Cl2 0.85 2.44 3.253(2) 159.8 3_565
O2 H202 Cl2 0.85 2.95 3.416(2) 116.3 1_545
O2 H201 Cl1 0.85 2.37 3.210(2) 171.4 1_545

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 939161'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?

_chemical_name_common            
'tetrachloride 1,2,4,5-tetra(1H-benzo[d]imidazol-2-yl)benzene dinuclear zinc (II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H22 Cl4 N8 Zn2, 4(C3 H7 N O)'
_chemical_formula_sum            'C46 H50 Cl4 N12 O4 Zn2'
_chemical_formula_weight         1107.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8612(10)
_cell_length_b                   25.265(3)
_cell_length_c                   11.1161(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.146(2)
_cell_angle_gamma                90.00
_cell_volume                     2583.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6709
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_T_max  0.6542
_exptl_absorpt_process_details   'SADABS (Bruker, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11185
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4534
_reflns_number_gt                3797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.8369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4534
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.70032(3) 0.149041(10) 0.45974(2) 0.02552(10) Uani 1 1 d . . .
Cl1 Cl 0.46267(6) 0.14971(2) 0.35020(6) 0.04118(17) Uani 1 1 d . . .
Cl2 Cl 0.82091(7) 0.22155(2) 0.44807(6) 0.03990(16) Uani 1 1 d . . .
N1 N 0.73886(18) 0.12394(7) 0.64224(17) 0.0250(4) Uani 1 1 d . . .
C1 C 0.8183(2) 0.14623(8) 0.7616(2) 0.0261(5) Uani 1 1 d . . .
C2 C 0.8950(3) 0.19411(9) 0.7922(2) 0.0330(5) Uani 1 1 d . . .
H2 H 0.8976 0.2180 0.7271 0.040 Uiso 1 1 calc R . .
C3 C 0.9662(3) 0.20478(10) 0.9209(2) 0.0375(6) Uani 1 1 d . . .
H3 H 1.0197 0.2368 0.9450 0.045 Uiso 1 1 calc R . .
C4 C 0.9624(3) 0.17001(10) 1.0174(2) 0.0382(6) Uani 1 1 d . . .
H4 H 1.0140 0.1789 1.1051 0.046 Uiso 1 1 calc R . .
C5 C 0.8853(2) 0.12295(10) 0.9887(2) 0.0332(5) Uani 1 1 d . . .
H5 H 0.8822 0.0994 1.0542 0.040 Uiso 1 1 calc R . .
C6 C 0.8132(2) 0.11228(9) 0.8589(2) 0.0256(5) Uani 1 1 d . . .
N2 N 0.72923(19) 0.06996(7) 0.79600(17) 0.0251(4) Uani 1 1 d . . .
H2A H 0.7062 0.0424 0.8330 0.030 Uiso 1 1 calc R . .
C7 C 0.6885(2) 0.07808(8) 0.6680(2) 0.0234(4) Uani 1 1 d . . .
C8 C 0.5943(2) 0.03956(8) 0.5749(2) 0.0228(4) Uani 1 1 d . . .
C9 C 0.6152(2) 0.01944(8) 0.4646(2) 0.0233(4) Uani 1 1 d . . .
C10 C 0.7343(2) 0.03378(8) 0.4204(2) 0.0242(5) Uani 1 1 d . . .
N3 N 0.79924(19) -0.00309(7) 0.37080(18) 0.0264(4) Uani 1 1 d . . .
H3A H 0.7775 -0.0370 0.3609 0.032 Uiso 1 1 calc R . .
C11 C 0.9057(2) 0.02210(9) 0.3385(2) 0.0263(5) Uani 1 1 d . . .
C12 C 1.0062(2) 0.00370(10) 0.2874(2) 0.0332(5) Uani 1 1 d . . .
H12 H 1.0082 -0.0323 0.2630 0.040 Uiso 1 1 calc R . .
C13 C 1.1027(3) 0.04035(10) 0.2739(2) 0.0360(6) Uani 1 1 d . . .
H13 H 1.1740 0.0292 0.2403 0.043 Uiso 1 1 calc R . .
C14 C 1.0997(2) 0.09324(10) 0.3077(2) 0.0339(5) Uani 1 1 d . . .
H14 H 1.1700 0.1169 0.2982 0.041 Uiso 1 1 calc R . .
C15 C 0.9972(2) 0.11206(10) 0.3545(2) 0.0295(5) Uani 1 1 d . . .
H15 H 0.9933 0.1484 0.3749 0.035 Uiso 1 1 calc R . .
C16 C 0.8995(2) 0.07541(9) 0.3707(2) 0.0242(5) Uani 1 1 d . . .
N4 N 0.78956(18) 0.08167(7) 0.42014(17) 0.0237(4) Uani 1 1 d . . .
C17 C 0.4800(2) 0.01964(8) 0.6064(2) 0.0241(5) Uani 1 1 d . . .
H17 H 0.4659 0.0334 0.6805 0.029 Uiso 1 1 calc R . .
O1 O 0.7767(3) 0.39476(8) 0.1947(2) 0.0625(6) Uani 1 1 d . . .
C18 C 0.7214(4) 0.35112(11) 0.1583(3) 0.0495(7) Uani 1 1 d . . .
H18 H 0.6186 0.3486 0.1318 0.059 Uiso 1 1 calc R . .
N5 N 0.7920(2) 0.30824(8) 0.1532(2) 0.0395(5) Uani 1 1 d . . .
C19 C 0.9499(3) 0.30817(14) 0.1923(3) 0.0624(9) Uani 1 1 d . . .
H19A H 0.9905 0.2790 0.2527 0.094 Uiso 1 1 calc R . .
H19B H 0.9888 0.3419 0.2342 0.094 Uiso 1 1 calc R . .
H19C H 0.9765 0.3036 0.1160 0.094 Uiso 1 1 calc R . .
C20 C 0.7193(3) 0.25833(11) 0.1053(3) 0.0541(8) Uani 1 1 d . . .
H20A H 0.6157 0.2616 0.0914 0.081 Uiso 1 1 calc R . .
H20B H 0.7626 0.2303 0.1686 0.081 Uiso 1 1 calc R . .
H20C H 0.7306 0.2494 0.0236 0.081 Uiso 1 1 calc R . .
O4 O 0.6624(3) -0.01352(9) 0.9152(2) 0.0689(6) Uani 1 1 d . . .
C211 C 0.6851(6) -0.0578(2) 0.9476(5) 0.0522(16) Uani 0.603(7) 1 d P A 1
H211 H 0.7828 -0.0692 0.9690 0.063 Uiso 0.603(7) 1 calc PR A 1
C212 C 0.5780(10) -0.0433(3) 0.9186(7) 0.048(2) Uani 0.397(7) 1 d P A 2
H212 H 0.4809 -0.0305 0.8886 0.057 Uiso 0.397(7) 1 calc PR A 2
N6 N 0.5937(2) -0.09380(8) 0.9585(2) 0.0393(5) Uani 1 1 d . . .
C221 C 0.4447(6) -0.0838(3) 0.9273(6) 0.0592(17) Uani 0.603(7) 1 d P A 1
H22A H 0.4232 -0.0471 0.8982 0.089 Uiso 0.603(7) 1 calc PR A 1
H22B H 0.4191 -0.0896 1.0036 0.089 Uiso 0.603(7) 1 calc PR A 1
H22C H 0.3880 -0.1079 0.8582 0.089 Uiso 0.603(7) 1 calc PR A 1
C231 C 0.6441(8) -0.1489(2) 0.9941(6) 0.0592(18) Uani 0.603(7) 1 d P A 1
H23A H 0.5984 -0.1723 0.9202 0.089 Uiso 0.603(7) 1 calc PR A 1
H23B H 0.6172 -0.1604 1.0667 0.089 Uiso 0.603(7) 1 calc PR A 1
H23C H 0.7500 -0.1505 1.0190 0.089 Uiso 0.603(7) 1 calc PR A 1
C222 C 0.4582(12) -0.1240(6) 0.9518(11) 0.087(4) Uani 0.397(7) 1 d P A 2
H22D H 0.3740 -0.1002 0.9223 0.131 Uiso 0.397(7) 1 calc PR A 2
H22E H 0.4703 -0.1377 1.0376 0.131 Uiso 0.397(7) 1 calc PR A 2
H22F H 0.4426 -0.1536 0.8912 0.131 Uiso 0.397(7) 1 calc PR A 2
C232 C 0.7235(11) -0.1220(4) 0.9940(8) 0.061(3) Uani 0.397(7) 1 d P A 2
H23D H 0.7117 -0.1522 0.9356 0.092 Uiso 0.397(7) 1 calc PR A 2
H23E H 0.7492 -0.1349 1.0826 0.092 Uiso 0.397(7) 1 calc PR A 2
H23F H 0.8009 -0.0989 0.9887 0.092 Uiso 0.397(7) 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.0263(18) . ?
Zn1 N4 2.0360(17) . ?
Zn1 Cl2 2.2131(6) . ?
Zn1 Cl1 2.2173(7) . ?
N1 C7 1.332(3) . ?
N1 C1 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.378(3) . ?
N2 C7 1.347(3) . ?
N2 H2A 0.8800 . ?
C7 C8 1.479(3) . ?
C8 C17 1.390(3) . ?
C8 C9 1.410(3) . ?
C9 C17 1.394(3) 3_656 ?
C9 C10 1.473(3) . ?
C10 N4 1.327(3) . ?
C10 N3 1.355(3) . ?
N3 C11 1.381(3) . ?
N3 H3A 0.8800 . ?
C11 C12 1.389(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 N4 1.390(3) . ?
C17 C9 1.394(3) 3_656 ?
C17 H17 0.9500 . ?
O1 C18 1.232(3) . ?
C18 N5 1.300(3) . ?
C18 H18 0.9500 . ?
N5 C20 1.453(3) . ?
N5 C19 1.457(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O4 C212 1.133(8) . ?
O4 C211 1.171(6) . ?
C211 N6 1.318(5) . ?
C211 H211 0.9500 . ?
C212 N6 1.340(8) . ?
C212 H212 0.9500 . ?
N6 C232 1.392(8) . ?
N6 C221 1.405(6) . ?
N6 C231 1.484(5) . ?
N6 C222 1.517(9) . ?
C221 H22A 0.9800 . ?
C221 H22B 0.9800 . ?
C221 H22C 0.9800 . ?
C231 H23A 0.9800 . ?
C231 H23B 0.9800 . ?
C231 H23C 0.9800 . ?
C222 H22D 0.9800 . ?
C222 H22E 0.9800 . ?
C222 H22F 0.9800 . ?
C232 H23D 0.9800 . ?
C232 H23E 0.9800 . ?
C232 H23F 0.9800 . ?

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
_geom_angle_publ_flag
N1 Zn1 N4 90.87(7) . . ?
N1 Zn1 Cl2 114.02(5) . . ?
N4 Zn1 Cl2 113.33(5) . . ?
N1 Zn1 Cl1 109.36(5) . . ?
N4 Zn1 Cl1 109.95(5) . . ?
Cl2 Zn1 Cl1 116.45(3) . . ?
C7 N1 C1 105.78(18) . . ?
C7 N1 Zn1 122.54(14) . . ?
C1 N1 Zn1 131.66(15) . . ?
N1 C1 C6 108.93(18) . . ?
N1 C1 C2 130.4(2) . . ?
C6 C1 C2 120.6(2) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.1(2) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
N2 C6 C5 131.9(2) . . ?
N2 C6 C1 105.44(19) . . ?
C5 C6 C1 122.6(2) . . ?
C7 N2 C6 108.26(18) . . ?
C7 N2 H2A 125.9 . . ?
C6 N2 H2A 125.9 . . ?
N1 C7 N2 111.56(18) . . ?
N1 C7 C8 127.63(19) . . ?
N2 C7 C8 120.76(18) . . ?
C17 C8 C9 118.37(19) . . ?
C17 C8 C7 115.06(19) . . ?
C9 C8 C7 126.45(18) . . ?
C17 C9 C8 117.91(19) 3_656 . ?
C17 C9 C10 116.14(19) 3_656 . ?
C8 C9 C10 125.86(19) . . ?
N4 C10 N3 111.79(18) . . ?
N4 C10 C9 127.04(19) . . ?
N3 C10 C9 121.16(19) . . ?
C10 N3 C11 107.70(18) . . ?
C10 N3 H3A 126.2 . . ?
C11 N3 H3A 126.2 . . ?
N3 C11 C12 132.4(2) . . ?
N3 C11 C16 105.64(18) . . ?
C12 C11 C16 122.0(2) . . ?
C13 C12 C11 116.3(2) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C12 C13 C14 122.3(2) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 117.1(2) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
N4 C16 C15 130.5(2) . . ?
N4 C16 C11 108.80(18) . . ?
C15 C16 C11 120.7(2) . . ?
C10 N4 C16 106.05(17) . . ?
C10 N4 Zn1 123.50(14) . . ?
C16 N4 Zn1 129.80(14) . . ?
C8 C17 C9 123.7(2) . 3_656 ?
C8 C17 H17 118.1 . . ?
C9 C17 H17 118.1 3_656 . ?
O1 C18 N5 125.4(3) . . ?
O1 C18 H18 117.3 . . ?
N5 C18 H18 117.3 . . ?
C18 N5 C20 122.5(2) . . ?
C18 N5 C19 121.3(2) . . ?
C20 N5 C19 116.2(2) . . ?
N5 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C212 O4 C211 54.3(4) . . ?
O4 C211 N6 128.8(5) . . ?
O4 C211 H211 115.6 . . ?
N6 C211 H211 115.6 . . ?
O4 C212 N6 130.2(8) . . ?
O4 C212 H212 114.9 . . ?
N6 C212 H212 114.9 . . ?
C211 N6 C212 46.6(4) . . ?
C211 N6 C232 77.9(5) . . ?
C212 N6 C232 124.5(6) . . ?
C211 N6 C221 122.9(4) . . ?
C212 N6 C221 76.3(4) . . ?
C232 N6 C221 159.1(5) . . ?
C211 N6 C231 119.9(4) . . ?
C212 N6 C231 165.6(5) . . ?
C232 N6 C231 42.1(4) . . ?
C221 N6 C231 117.0(4) . . ?
C211 N6 C222 164.4(6) . . ?
C212 N6 C222 117.9(7) . . ?
C232 N6 C222 117.3(7) . . ?
C221 N6 C222 41.7(5) . . ?
C231 N6 C222 75.3(6) . . ?
N6 C221 H22A 109.5 . . ?
N6 C221 H22B 109.5 . . ?
N6 C221 H22C 109.5 . . ?
N6 C231 H23A 109.5 . . ?
N6 C231 H23B 109.5 . . ?
N6 C231 H23C 109.5 . . ?
N6 C222 H22D 109.5 . . ?
N6 C222 H22E 109.5 . . ?
H22D C222 H22E 109.5 . . ?
N6 C222 H22F 109.5 . . ?
H22D C222 H22F 109.5 . . ?
H22E C222 H22F 109.5 . . ?
N6 C232 H23D 109.5 . . ?
N6 C232 H23E 109.5 . . ?
H23D C232 H23E 109.5 . . ?
N6 C232 H23F 109.5 . . ?
H23D C232 H23F 109.5 . . ?
H23E C232 H23F 109.5 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Zn1 N1 C7 -56.49(17) . . . . ?
Cl2 Zn1 N1 C7 -172.62(14) . . . . ?
Cl1 Zn1 N1 C7 55.05(17) . . . . ?
N4 Zn1 N1 C1 121.94(19) . . . . ?
Cl2 Zn1 N1 C1 5.8(2) . . . . ?
Cl1 Zn1 N1 C1 -126.52(18) . . . . ?
C7 N1 C1 C6 -0.2(2) . . . . ?
Zn1 N1 C1 C6 -178.83(15) . . . . ?
C7 N1 C1 C2 179.9(2) . . . . ?
Zn1 N1 C1 C2 1.3(4) . . . . ?
N1 C1 C2 C3 -178.6(2) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 N2 179.1(2) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
N1 C1 C6 N2 -0.4(2) . . . . ?
C2 C1 C6 N2 179.5(2) . . . . ?
N1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C5 C6 N2 C7 -177.7(2) . . . . ?
C1 C6 N2 C7 0.8(2) . . . . ?
C1 N1 C7 N2 0.7(2) . . . . ?
Zn1 N1 C7 N2 179.53(13) . . . . ?
C1 N1 C7 C8 178.2(2) . . . . ?
Zn1 N1 C7 C8 -3.0(3) . . . . ?
C6 N2 C7 N1 -1.0(2) . . . . ?
C6 N2 C7 C8 -178.71(19) . . . . ?
N1 C7 C8 C17 -135.3(2) . . . . ?
N2 C7 C8 C17 42.0(3) . . . . ?
N1 C7 C8 C9 48.9(3) . . . . ?
N2 C7 C8 C9 -133.8(2) . . . . ?
C17 C8 C9 C17 -0.3(3) . . . 3_656 ?
C7 C8 C9 C17 175.4(2) . . . 3_656 ?
C17 C8 C9 C10 -176.7(2) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C17 C9 C10 N4 143.0(2) 3_656 . . . ?
C8 C9 C10 N4 -40.6(3) . . . . ?
C17 C9 C10 N3 -35.6(3) 3_656 . . . ?
C8 C9 C10 N3 140.8(2) . . . . ?
N4 C10 N3 C11 1.3(2) . . . . ?
C9 C10 N3 C11 -179.95(19) . . . . ?
C10 N3 C11 C12 178.4(2) . . . . ?
C10 N3 C11 C16 -0.4(2) . . . . ?
N3 C11 C12 C13 -176.6(2) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C13 C14 C15 C16 2.1(3) . . . . ?
C14 C15 C16 N4 177.1(2) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
N3 C11 C16 N4 -0.6(2) . . . . ?
C12 C11 C16 N4 -179.6(2) . . . . ?
N3 C11 C16 C15 177.70(19) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
N3 C10 N4 C16 -1.7(2) . . . . ?
C9 C10 N4 C16 179.7(2) . . . . ?
N3 C10 N4 Zn1 169.90(14) . . . . ?
C9 C10 N4 Zn1 -8.8(3) . . . . ?
C15 C16 N4 C10 -176.7(2) . . . . ?
C11 C16 N4 C10 1.4(2) . . . . ?
C15 C16 N4 Zn1 12.4(3) . . . . ?
C11 C16 N4 Zn1 -169.45(15) . . . . ?
N1 Zn1 N4 C10 63.89(17) . . . . ?
Cl2 Zn1 N4 C10 -179.37(15) . . . . ?
Cl1 Zn1 N4 C10 -47.10(18) . . . . ?
N1 Zn1 N4 C16 -126.70(18) . . . . ?
Cl2 Zn1 N4 C16 -10.0(2) . . . . ?
Cl1 Zn1 N4 C16 122.31(17) . . . . ?
C9 C8 C17 C9 0.4(4) . . . 3_656 ?
C7 C8 C17 C9 -175.8(2) . . . 3_656 ?
O1 C18 N5 C20 -178.0(3) . . . . ?
O1 C18 N5 C19 0.2(5) . . . . ?
C212 O4 C211 N6 -2.8(6) . . . . ?
C211 O4 C212 N6 2.8(6) . . . . ?
O4 C211 N6 C212 2.6(5) . . . . ?
O4 C211 N6 C232 179.3(7) . . . . ?
O4 C211 N6 C221 1.8(8) . . . . ?
O4 C211 N6 C231 176.3(5) . . . . ?
O4 C211 N6 C222 11(2) . . . . ?
O4 C212 N6 C211 -2.8(6) . . . . ?
O4 C212 N6 C232 -6.6(11) . . . . ?
O4 C212 N6 C221 176.5(9) . . . . ?
O4 C212 N6 C231 -25(2) . . . . ?
O4 C212 N6 C222 179.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.88 1.82 2.696(3) 177.9 .
N3 H3A O1 0.88 1.84 2.713(3) 168.4 2_645

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 939162'
