##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'APEX3 v2015.5-2'
_journal_date_recd_electronic     2016-02-24
_journal_date_accepted     2016-05-11
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      6
_journal_page_first     491
_journal_page_last     497
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616007798
_journal_coeditor_code     UK3125
_publ_contact_author_name     'David K. Geiger'
_publ_contact_author_address
;
Department of Chemistry
SUNY--College at Geneseo
Geneseo, NY 14454
USA
;
_publ_contact_author_email     geiger@geneseo.edu
_publ_contact_author_fax     '585-245-5288'
_publ_contact_author_phone     '585-245-5452'
_publ_section_title
;
Structural and spectroscopic characterization of two new blue luminescent
pyridylbenzimidazole zinc(II) complexes
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'DeStefano, Matthew R.' .
;
Department of Chemistry
SUNY--College at Geneseo
Geneseo, NY 14454
USA
;
    'Geiger, David K.' .
;
Department of Chemistry
SUNY--College at Geneseo
Geneseo, NY 14454
USA
;
_publ_section_synopsis
;
The structures of two zinc(II) complexes of
5,6-dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)methyl]-1H-benzimidazole
were determined. The absorption and emission data of the complexes and the
free ligand are reported. The spectra are examined in the context of a
frontier orbital analysis based on DFT calculations of the benzimidazole
ligand and the zinc(II) complexes.
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1479261'
_chemical_name_systematic
;\
Dichlorido(dimethylformamide-κO){5,6-dimethyl-2-(pyridin-2-yl-\
κN)-1-[(pyridin-2-yl)methyl]-1H-benzimidazole-\
κN³}zinc(II) dimethylformamide monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H25 Cl2 N5 O Zn, C3 H7 N O'
_chemical_formula_sum     'C26 H32 Cl2 N6 O2 Zn'
_chemical_formula_iupac     '[Zn Cl2 (C20 H18 N4) (C3 H7 N O)], C3 H7 N O'
_chemical_formula_weight     596.84
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     11.2504(11)
_cell_length_b     11.7298(11)
_cell_length_c     12.6588(13)
_cell_angle_alpha     71.518(4)
_cell_angle_beta     71.087(3)
_cell_angle_gamma     65.760(3)
_cell_volume     1407.9(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4156
_cell_measurement_theta_min     2.3609
_cell_measurement_theta_max     25.2212
_cell_measurement_temperature     200.(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.580
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     620
_exptl_absorpt_coefficient_mu     1.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.56
_exptl_absorpt_correction_T_max     0.81
_exptl_special_details
;
;
_diffrn_ambient_temperature     200.(2)
_diffrn_radiation_type     MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S benchtop'
_diffrn_measurement_method     '/w scans'
_diffrn_detector_area_resol_mean     8.3330
_diffrn_reflns_number     12063
_diffrn_reflns_av_R_equivalents     0.0470
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     25.39
_diffrn_reflns_theta_full     25.39
_diffrn_measured_fraction_theta_max     0.959
_diffrn_measured_fraction_theta_full     0.959
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_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.
;
_reflns_number_total     4976
_reflns_number_gt     4058
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0522
_refine_ls_R_factor_gt     0.0398
_refine_ls_wR_factor_gt     0.0992
_refine_ls_wR_factor_ref     0.1066
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     4976
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.403
_refine_diff_density_min     -0.639
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    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'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Zn Zn1 0.56523(3) 0.12184(3) 0.66858(2) 0.02769(12) Uani d 1 . .
    Cl Cl1 0.47553(7) -0.03597(7) 0.75730(6) 0.0398(2) Uani d 1 . .
    Cl Cl2 0.76891(8) 0.08344(8) 0.69805(8) 0.0539(2) Uani d 1 . .
    O O1 0.6512(2) 0.0607(2) 0.51059(17) 0.0518(6) Uani d 1 . .
    O O2 0.0887(3) 0.7101(3) 0.8691(2) 0.0719(8) Uani d 1 . .
    N N1 0.4590(2) 0.2990(2) 0.58394(16) 0.0224(5) Uani d 1 . .
    N N2 0.4455(2) 0.2320(2) 0.80622(17) 0.0273(5) Uani d 1 . .
    N N3 0.31680(19) 0.4993(2) 0.58193(16) 0.0215(5) Uani d 1 . .
    N N4 0.0522(2) 0.5219(2) 0.6568(2) 0.0325(6) Uani d 1 . .
    N N5 0.7837(2) -0.0957(2) 0.41491(19) 0.0343(6) Uani d 1 . .
    N N6 -0.0489(3) 0.8385(3) 0.9914(2) 0.0465(7) Uani d 1 . .
    C C1 0.4522(2) 0.3607(3) 0.4705(2) 0.0211(5) Uani d 1 . .
    C C2 0.5174(2) 0.3181(3) 0.3683(2) 0.0238(6) Uani d 1 . .
    H H2 0.579 0.2334 0.3682 0.029 Uiso calc 1 . .
    C C3 0.4897(3) 0.4032(3) 0.2668(2) 0.0268(6) Uani d 1 . .
    C C4 0.3968(3) 0.5294(3) 0.2673(2) 0.0280(6) Uani d 1 . .
    C C5 0.3328(3) 0.5717(3) 0.3681(2) 0.0267(6) Uani d 1 . .
    H H5 0.2708 0.6563 0.3687 0.032 Uiso calc 1 . .
    C C6 0.3625(2) 0.4858(3) 0.4689(2) 0.0220(6) Uani d 1 . .
    C C7 0.3752(2) 0.3848(3) 0.6468(2) 0.0217(6) Uani d 1 . .
    C C8 0.3564(2) 0.3466(3) 0.7727(2) 0.0237(6) Uani d 1 . .
    C C9 0.2576(3) 0.4158(3) 0.8511(2) 0.0328(7) Uani d 1 . .
    H H9 0.1939 0.4962 0.8265 0.039 Uiso calc 1 . .
    C C10 0.2550(3) 0.3634(3) 0.9669(2) 0.0398(8) Uani d 1 . .
    H H10 0.1883 0.4081 1.0226 0.048 Uiso calc 1 . .
    C C11 0.3478(3) 0.2481(3) 1.0008(2) 0.0402(8) Uani d 1 . .
    H H11 0.3481 0.2127 1.0795 0.048 Uiso calc 1 . .
    C C12 0.4417(3) 0.1841(3) 0.9170(2) 0.0351(7) Uani d 1 . .
    H H12 0.5056 0.1031 0.9398 0.042 Uiso calc 1 . .
    C C13 0.2217(2) 0.6187(3) 0.6145(2) 0.0246(6) Uani d 1 . .
    H H13A 0.2355 0.6912 0.5517 0.03 Uiso calc 1 . .
    H H13B 0.24 0.6266 0.6828 0.03 Uiso calc 1 . .
    C C14 0.0774(2) 0.6283(2) 0.64060(19) 0.0215(6) Uani d 1 . .
    C C15 -0.0220(3) 0.7448(3) 0.6523(2) 0.0280(6) Uani d 1 . .
    H H15 0.0004 0.819 0.6375 0.034 Uiso calc 1 . .
    C C16 -0.1542(3) 0.7525(3) 0.6858(2) 0.0349(7) Uani d 1 . .
    H H16 -0.2241 0.8311 0.6967 0.042 Uiso calc 1 . .
    C C17 -0.1819(3) 0.6432(3) 0.7029(3) 0.0395(8) Uani d 1 . .
    H H17 -0.2716 0.6445 0.7262 0.047 Uiso calc 1 . .
    C C18 -0.0776(3) 0.5329(3) 0.6855(3) 0.0425(8) Uani d 1 . .
    H H18 -0.098 0.459 0.6942 0.051 Uiso calc 1 . .
    C C19 0.6822(3) -0.0471(3) 0.4948(2) 0.0365(7) Uani d 1 . .
    H H19 0.63 -0.0982 0.5431 0.044 Uiso calc 1 . .
    C C20 0.8633(4) -0.0198(4) 0.3359(4) 0.0749(14) Uani d 1 . .
    H H20A 0.9574 -0.0648 0.3398 0.112 Uiso calc 1 . .
    H H20B 0.8319 0.0632 0.3565 0.112 Uiso calc 1 . .
    H H20C 0.8544 -0.0065 0.258 0.112 Uiso calc 1 . .
    C C21 0.8162(4) -0.2229(3) 0.3986(3) 0.0524(9) Uani d 1 . .
    H H21A 0.9098 -0.273 0.402 0.079 Uiso calc 1 . .
    H H21B 0.8031 -0.2166 0.3239 0.079 Uiso calc 1 . .
    H H21C 0.7579 -0.265 0.4589 0.079 Uiso calc 1 . .
    C C22 -0.0046(3) 0.8047(3) 0.8915(3) 0.0466(8) Uani d 1 . .
    H H22 -0.0499 0.8593 0.8325 0.056 Uiso calc 1 . .
    C C23 0.0117(5) 0.7549(5) 1.0860(3) 0.0915(16) Uani d 1 . .
    H H23A 0.0968 0.6918 1.0572 0.137 Uiso calc 1 . .
    H H23B -0.0485 0.7106 1.14 0.137 Uiso calc 1 . .
    H H23C 0.0278 0.8057 1.1247 0.137 Uiso calc 1 . .
    C C24 -0.1634(4) 0.9519(4) 1.0116(4) 0.0724(12) Uani d 1 . .
    H H24A -0.1972 0.9956 0.9417 0.109 Uiso calc 1 . .
    H H24B -0.1369 1.0095 1.0335 0.109 Uiso calc 1 . .
    H H24C -0.2337 0.9276 1.0733 0.109 Uiso calc 1 . .
    C C31 0.5605(3) 0.3587(3) 0.1557(2) 0.0371(7) Uani d 1 . .
    H H31A 0.6122 0.2671 0.1718 0.056 Uiso calc 1 . .
    H H31B 0.6209 0.4063 0.1097 0.056 Uiso calc 1 . .
    H H31C 0.4943 0.3741 0.1134 0.056 Uiso calc 1 . .
    C C41 0.3633(3) 0.6185(3) 0.1564(2) 0.0411(8) Uani d 1 . .
    H H41A 0.3034 0.7032 0.1709 0.062 Uiso calc 1 . .
    H H41B 0.319 0.5842 0.1251 0.062 Uiso calc 1 . .
    H H41C 0.4458 0.6258 0.1015 0.062 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C1 . 1.400(3) ?
    C9 C10 . 1.394(4) ?
    C10 C11 . 1.366(5) ?
    C11 C12 . 1.390(4) ?
    N2 C12 . 1.329(3) ?
    N3 C13 . 1.459(3) ?
    C13 C14 . 1.511(3) ?
    N4 C14 . 1.331(3) ?
    C14 C15 . 1.380(4) ?
    C15 C16 . 1.380(4) ?
    C16 C17 . 1.378(4) ?
    C17 C18 . 1.366(4) ?
    N4 C18 . 1.346(3) ?
    N5 C19 . 1.317(3) ?
    O1 C19 . 1.229(3) ?
    C1 C2 . 1.398(3) ?
    N5 C20 . 1.451(4) ?
    N5 C21 . 1.448(4) ?
    N6 C22 . 1.323(4) ?
    O2 C22 . 1.211(4) ?
    N6 C23 . 1.448(5) ?
    N6 C24 . 1.445(4) ?
    C2 C3 . 1.391(4) ?
    C3 C31 . 1.511(3) ?
    C3 C4 . 1.419(4) ?
    C4 C41 . 1.514(4) ?
    C4 C5 . 1.381(4) ?
    C5 C6 . 1.392(4) ?
    C1 C6 . 1.396(4) ?
    N3 C6 . 1.392(3) ?
    N3 C7 . 1.355(3) ?
    N1 C7 . 1.333(3) ?
    C7 C8 . 1.481(3) ?
    N2 C8 . 1.341(3) ?
    C8 C9 . 1.391(3) ?
    Zn1 Cl1 . 2.2775(8) yes
    Zn1 Cl2 . 2.2788(9) yes
    C10 H10 . 0.95 ?
    C11 H11 . 0.95 ?
    C12 H12 . 0.95 ?
    C13 H13A . 0.99 ?
    C13 H13B . 0.99 ?
    C15 H15 . 0.95 ?
    C16 H16 . 0.95 ?
    C17 H17 . 0.95 ?
    C18 H18 . 0.95 ?
    C19 H19 . 0.95 ?
    C2 H2 . 0.95 ?
    C20 H20A . 0.98 ?
    C20 H20B . 0.98 ?
    C20 H20C . 0.98 ?
    C21 H21A . 0.98 ?
    C21 H21B . 0.98 ?
    C21 H21C . 0.98 ?
    C22 H22 . 0.95 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
    C24 H24A . 0.98 ?
    C24 H24B . 0.98 ?
    C24 H24C . 0.98 ?
    C31 H31A . 0.98 ?
    C31 H31B . 0.98 ?
    C31 H31C . 0.98 ?
    C41 H41A . 0.98 ?
    C41 H41B . 0.98 ?
    C41 H41C . 0.98 ?
    C5 H5 . 0.95 ?
    C9 H9 . 0.95 ?
    Zn1 N1 . 2.067(2) yes
    Zn1 N2 . 2.235(2) yes
    Zn1 O1 . 2.1298(19) yes
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
    N1 Zn1 O1 . . 89.50(8) y
    N1 Zn1 N2 . . 75.63(8) y
    O1 Zn1 N2 . . 165.10(9) y
    N1 Zn1 Cl1 . . 122.26(6) y
    O1 Zn1 Cl1 . . 94.81(6) y
    N2 Zn1 Cl1 . . 92.36(6) y
    N1 Zn1 Cl2 . . 121.19(6) y
    O1 Zn1 Cl2 . . 92.71(7) y
    N2 Zn1 Cl2 . . 95.85(6) y
    Cl1 Zn1 Cl2 . . 116.08(3) y
    C19 O1 Zn1 . . 127.57(18) ?
    C7 N1 C1 . . 105.8(2) ?
    C7 N1 Zn1 . . 117.44(16) ?
    C1 N1 Zn1 . . 136.71(17) ?
    C12 N2 C8 . . 119.5(2) ?
    C12 N2 Zn1 . . 124.7(2) ?
    C8 N2 Zn1 . . 114.86(16) ?
    C7 N3 C6 . . 107.0(2) ?
    C7 N3 C13 . . 130.6(2) ?
    C6 N3 C13 . . 122.4(2) ?
    C14 N4 C18 . . 116.3(2) ?
    C19 N5 C21 . . 122.0(2) ?
    C19 N5 C20 . . 120.3(3) ?
    C21 N5 C20 . . 117.6(2) ?
    C22 N6 C24 . . 121.8(3) ?
    C22 N6 C23 . . 119.4(3) ?
    C24 N6 C23 . . 118.7(3) ?
    C6 C1 C2 . . 120.1(2) ?
    C6 C1 N1 . . 108.5(2) ?
    C2 C1 N1 . . 131.4(3) ?
    C3 C2 C1 . . 118.2(3) ?
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C2 C3 C4 . . 120.8(2) ?
    C2 C3 C31 . . 118.7(3) ?
    C4 C3 C31 . . 120.5(2) ?
    C5 C4 C3 . . 121.0(2) ?
    C5 C4 C41 . . 119.0(3) ?
    C3 C4 C41 . . 120.0(2) ?
    C4 C5 C6 . . 117.4(3) ?
    C4 C5 H5 . . 121.3 ?
    C6 C5 H5 . . 121.3 ?
    N3 C6 C5 . . 131.2(2) ?
    N3 C6 C1 . . 106.3(2) ?
    C5 C6 C1 . . 122.4(2) ?
    N1 C7 N3 . . 112.3(2) ?
    N1 C7 C8 . . 119.0(2) ?
    N3 C7 C8 . . 128.7(2) ?
    N2 C8 C9 . . 121.7(2) ?
    N2 C8 C7 . . 112.1(2) ?
    C9 C8 C7 . . 126.1(3) ?
    C8 C9 C10 . . 117.8(3) ?
    C8 C9 H9 . . 121.1 ?
    C10 C9 H9 . . 121.1 ?
    C11 C10 C9 . . 120.4(3) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C10 C11 C12 . . 118.1(3) ?
    C10 C11 H11 . . 120.9 ?
    C12 C11 H11 . . 120.9 ?
    N2 C12 C11 . . 122.4(3) ?
    N2 C12 H12 . . 118.8 ?
    C11 C12 H12 . . 118.8 ?
    N3 C13 C14 . . 113.5(2) ?
    N3 C13 H13A . . 108.9 ?
    C14 C13 H13A . . 108.9 ?
    N3 C13 H13B . . 108.9 ?
    C14 C13 H13B . . 108.9 ?
    H13A C13 H13B . . 107.7 ?
    N4 C14 C15 . . 123.0(2) ?
    N4 C14 C13 . . 118.0(2) ?
    C15 C14 C13 . . 118.9(2) ?
    C16 C15 C14 . . 119.5(2) ?
    C16 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    C17 C16 C15 . . 118.1(3) ?
    C17 C16 H16 . . 120.9 ?
    C15 C16 H16 . . 120.9 ?
    C18 C17 C16 . . 118.5(3) ?
    C18 C17 H17 . . 120.7 ?
    C16 C17 H17 . . 120.7 ?
    N4 C18 C17 . . 124.4(3) ?
    N4 C18 H18 . . 117.8 ?
    C17 C18 H18 . . 117.8 ?
    O1 C19 N5 . . 123.8(3) ?
    O1 C19 H19 . . 118.1 ?
    N5 C19 H19 . . 118.1 ?
    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 ?
    N5 C21 H21A . . 109.5 ?
    N5 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    N5 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O2 C22 N6 . . 125.5(3) ?
    O2 C22 H22 . . 117.3 ?
    N6 C22 H22 . . 117.3 ?
    N6 C23 H23A . . 109.5 ?
    N6 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    N6 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    N6 C24 H24A . . 109.5 ?
    N6 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    N6 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C3 C31 H31A . . 109.5 ?
    C3 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C3 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C4 C41 H41A . . 109.5 ?
    C4 C41 H41B . . 109.5 ?
    H41A C41 H41B . . 109.5 ?
    C4 C41 H41C . . 109.5 ?
    H41A C41 H41C . . 109.5 ?
    H41B C41 H41C . . 109.5 ?
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
    C2 H2 O1 . 0.95 2.30 3.034(4) 133.5
    C5 H5 Cl2 2_666 0.95 2.78 3.612(3) 146.7
    C9 H9 O2 . 0.95 2.45 3.226(4) 139.1
    C19 H19 Cl1 . 0.95 2.84 3.389(2) 117.8
data_II
_database_code_depnum_ccdc_archive     'CCDC 1479262'
_chemical_name_systematic
;\
Bis(acetato-κ²O,O'){5,6-dimethyl-2-(pyridin-2-yl-κN)-\
1-[(pyridin-2-yl)methyl]-1H-benzimidazole-κN³}zinc(II) ethanol
monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H24 N4 O4 Zn, C2 H6 O'
_chemical_formula_sum     'C26 H30 N4 O5 Zn'
_chemical_formula_iupac     'Zn (C2 H3 O2)2 (C20 H18 N4)], C2 H6 O'
_chemical_formula_weight     543.91
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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     16.0866(17)
_cell_length_b     8.7150(8)
_cell_length_c     18.745(2)
_cell_angle_alpha     90
_cell_angle_beta     94.193(4)
_cell_angle_gamma     90
_cell_volume     2620.9(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6456
_cell_measurement_theta_min     2.1757
_cell_measurement_theta_max     23.2337
_cell_measurement_temperature     200.(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'clear pale grey'
_exptl_crystal_size_max     0.600
_exptl_crystal_size_mid     0.400
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.378
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1136
_exptl_absorpt_coefficient_mu     0.980
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.67
_exptl_absorpt_correction_T_max     0.83
_exptl_special_details
;
;
_diffrn_ambient_temperature     200.(2)
_diffrn_radiation_type     'Mo Ka'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S benchtop'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     8.3330
_diffrn_reflns_number     23075
_diffrn_reflns_av_R_equivalents     0.0532
_diffrn_reflns_theta_min     2.54
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     22
_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.
;
_reflns_number_total     4636
_reflns_number_gt     3543
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0542
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.0823
_refine_ls_wR_factor_ref     0.0904
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     4636
_refine_ls_number_parameters     361
_refine_ls_number_restraints     4
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0415P)²+0.6452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.283
_refine_diff_density_min     -0.298
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and  Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Zn Zn1 1.00931(2) 0.64742(3) 0.76586(2) 0.03809(11) Uani d 1.0 . .
    O O1 1.11296(13) 0.5215(3) 0.78573(12) 0.0750(7) Uani d 1.0 . .
    O O2 1.05973(13) 0.4878(3) 0.67684(11) 0.0671(6) Uani d 1.0 . .
    O O3 0.95559(14) 0.8052(2) 0.69317(11) 0.0620(6) Uani d 1.0 . .
    O O4 1.06838(15) 0.8835(3) 0.75097(13) 0.0794(7) Uani d 1.0 . .
    N N1 0.89210(12) 0.5955(2) 0.95226(10) 0.0332(5) Uani d 1.0 . .
    N N2 0.96702(12) 0.6853(2) 0.86594(10) 0.0333(5) Uani d 1.0 . .
    N N3 0.89927(12) 0.5090(2) 0.76307(10) 0.0355(5) Uani d 1.0 . .
    N N4 0.71641(14) 0.6761(2) 0.96555(11) 0.0439(5) Uani d 1.0 . .
    C C1 1.00139(14) 0.7414(3) 0.93111(13) 0.0354(6) Uani d 1.0 . .
    C C2 1.06942(16) 0.8386(3) 0.94653(14) 0.0399(6) Uani d 1.0 . .
    H H2 1.1003 0.8785 0.9094 0.048 Uiso calc 1.0 . .
    C C3 1.09048(17) 0.8751(3) 1.01728(16) 0.0458(7) Uani d 1.0 . .
    C C4 1.04362(18) 0.8161(3) 1.07236(15) 0.0458(7) Uani d 1.0 . .
    C C5 0.97574(16) 0.7211(3) 1.05715(13) 0.0423(6) Uani d 1.0 . .
    H H5 0.9444 0.6815 1.0941 0.051 Uiso calc 1.0 . .
    C C6 0.95497(15) 0.6855(2) 0.98528(13) 0.0350(6) Uani d 1.0 . .
    C C7 0.90267(15) 0.6000(2) 0.88077(13) 0.0319(5) Uani d 1.0 . .
    C C8 0.85525(15) 0.5185(2) 0.82155(12) 0.0323(5) Uani d 1.0 . .
    C C9 0.77485(15) 0.4623(3) 0.82189(14) 0.0398(6) Uani d 1.0 . .
    H H9 0.7435 0.4747 0.8625 0.048 Uiso calc 1.0 . .
    C C10 0.74102(17) 0.3866(3) 0.76076(15) 0.0451(7) Uani d 1.0 . .
    H H10 0.6864 0.345 0.7598 0.054 Uiso calc 1.0 . .
    C C11 0.78682(17) 0.3726(3) 0.70210(14) 0.0453(7) Uani d 1.0 . .
    H H11 0.7651 0.3194 0.6606 0.054 Uiso calc 1.0 . .
    C C12 0.86535(17) 0.4380(3) 0.70506(13) 0.0419(6) Uani d 1.0 . .
    H H12 0.8964 0.432 0.664 0.05 Uiso calc 1.0 . .
    C C13 0.83317(15) 0.5064(3) 0.99180(13) 0.0386(6) Uani d 1.0 . .
    H H12A 0.8635 0.4581 1.0338 0.046 Uiso calc 1.0 . .
    H H13B 0.8091 0.4234 0.9607 0.046 Uiso calc 1.0 . .
    C C14 0.76361(15) 0.6042(3) 1.01669(13) 0.0358(6) Uani d 1.0 . .
    C C15 0.74968(18) 0.6147(3) 1.08821(14) 0.0511(7) Uani d 1.0 . .
    H H15 0.7841 0.5606 1.1231 0.061 Uiso calc 1.0 . .
    C C16 0.68468(19) 0.7054(4) 1.10838(16) 0.0644(9) Uani d 1.0 . .
    H H16 0.6743 0.7157 1.1574 0.077 Uiso calc 1.0 . .
    C C17 0.63584(19) 0.7799(4) 1.05690(16) 0.0620(8) Uani d 1.0 . .
    H H17 0.591 0.8431 1.0692 0.074 Uiso calc 1.0 . .
    C C18 0.65325(18) 0.7610(3) 0.98690(15) 0.0564(8) Uani d 1.0 . .
    H H18 0.6183 0.8114 0.9512 0.068 Uiso calc 1.0 . .
    C C19 1.1156(2) 0.4625(4) 0.72414(19) 0.0627(8) Uani d 1.0 . .
    C C20 1.1889(2) 0.3617(5) 0.7095(2) 0.1041(15) Uani d 1.0 . .
    H H20A 1.183 0.3264 0.6598 0.156 Uiso calc 1.0 . .
    H H20B 1.1905 0.2729 0.7417 0.156 Uiso calc 1.0 . .
    H H20C 1.2406 0.4205 0.7176 0.156 Uiso calc 1.0 . .
    C C21 1.0095(2) 0.9078(4) 0.70617(18) 0.0612(8) Uani d 1.0 . .
    C C22 1.0000(3) 1.0561(4) 0.6651(2) 0.0966(14) Uani d 1.0 . .
    H H22A 1.043 1.1287 0.6833 0.145 Uiso calc 1.0 . .
    H H22B 0.9448 1.0997 0.6711 0.145 Uiso calc 1.0 . .
    H H22C 1.0059 1.0365 0.6143 0.145 Uiso calc 1.0 . .
    C C31 1.16477(18) 0.9773(3) 1.03577(18) 0.0617(9) Uani d 1.0 . .
    H H31A 1.2078 0.9191 1.0638 0.093 Uiso calc 1.0 . .
    H H31B 1.1475 1.0651 1.0638 0.093 Uiso calc 1.0 . .
    H H31C 1.1872 1.0142 0.9917 0.093 Uiso calc 1.0 . .
    C C41 1.0660(2) 0.8603(3) 1.14974(16) 0.0636(9) Uani d 1.0 . .
    H H41A 1.0295 0.8056 1.1808 0.095 Uiso calc 1.0 . .
    H H41B 1.0588 0.9711 1.1555 0.095 Uiso calc 1.0 . .
    H H41C 1.1241 0.8325 1.1629 0.095 Uiso calc 1.0 . .
    O O50 0.6649(10) 0.2518(17) 0.9156(7) 0.077(4) Uani d 0.496(14) A 1
    H H50 0.6313 0.2702 0.8802 0.115 Uiso calc 0.496(14) A 1
    C C51 0.6223(8) 0.1850(13) 0.9699(5) 0.094(4) Uani d 0.496(14) A 1
    H H51A 0.6623 0.1272 1.0024 0.113 Uiso calc 0.496(14) A 1
    H H51B 0.5807 0.1114 0.9485 0.113 Uiso calc 0.496(14) A 1
    C C52 0.5814(7) 0.2963(13) 1.0097(7) 0.099(4) Uani d 0.496(14) A 1
    H H52A 0.6226 0.368 1.0318 0.148 Uiso calc 0.496(14) A 1
    H H52B 0.552 0.2453 1.0471 0.148 Uiso calc 0.496(14) A 1
    H H52C 0.5412 0.3528 0.9778 0.148 Uiso calc 0.496(14) A 1
    O O60 0.6600(11) 0.303(2) 0.9271(8) 0.101(5) Uani d 0.504(14) A 2
    H H60 0.62 0.2958 0.8958 0.151 Uiso calc 0.504(14) A 2
    C C61 0.6301(12) 0.292(2) 0.9948(8) 0.164(8) Uani d 0.504(14) A 2
    H H61A 0.5954 0.3833 1.0028 0.197 Uiso calc 0.504(14) A 2
    H H61B 0.6781 0.2939 1.031 0.197 Uiso calc 0.504(14) A 2
    C C62 0.5823(7) 0.1581(11) 1.0052(7) 0.102(4) Uani d 0.504(14) A 2
    H H62A 0.5439 0.1404 0.963 0.153 Uiso calc 0.504(14) A 2
    H H62B 0.5504 0.1716 1.0474 0.153 Uiso calc 0.504(14) A 2
    H H62C 0.6196 0.0696 1.0126 0.153 Uiso calc 0.504(14) 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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Zn1 O1 . 2.008(2) y
    Zn1 N2 . 2.068(2) y
    Zn1 O3 . 2.079(2) y
    Zn1 N3 . 2.139(2) y
    Zn1 O4 . 2.292(2) y
    Zn1 O2 . 2.362(2) y
    Zn1 C19 . 2.515(3) ?
    Zn1 C21 . 2.530(3) ?
    O1 C19 . 1.268(4) ?
    O2 C19 . 1.235(4) ?
    O3 C21 . 1.257(4) ?
    O4 C21 . 1.237(4) ?
    N1 C7 . 1.364(3) ?
    N1 C6 . 1.389(3) ?
    N1 C13 . 1.467(3) ?
    N2 C7 . 1.320(3) ?
    N2 C1 . 1.392(3) ?
    N3 C12 . 1.333(3) ?
    N3 C8 . 1.350(3) ?
    N4 C14 . 1.335(3) ?
    N4 C18 . 1.342(3) ?
    C1 C6 . 1.392(3) ?
    C1 C2 . 1.398(3) ?
    C2 C3 . 1.382(4) ?
    C2 H2 . 0.95 ?
    C3 C4 . 1.419(4) ?
    C3 C31 . 1.511(4) ?
    C4 C5 . 1.383(4) ?
    C4 C41 . 1.518(4) ?
    C5 C6 . 1.399(3) ?
    C5 H5 . 0.95 ?
    C7 C8 . 1.481(3) ?
    C8 C9 . 1.384(3) ?
    C9 C10 . 1.397(3) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.373(4) ?
    C10 H10 . 0.95 ?
    C11 C12 . 1.383(4) ?
    C11 H11 . 0.95 ?
    C12 H12 . 0.95 ?
    C13 C14 . 1.507(3) ?
    C13 H12A . 0.99 ?
    C13 H13B . 0.99 ?
    C14 C15 . 1.378(3) ?
    C15 C16 . 1.386(4) ?
    C15 H15 . 0.95 ?
    C16 C17 . 1.363(4) ?
    C16 H16 . 0.95 ?
    C17 C18 . 1.371(4) ?
    C17 H17 . 0.95 ?
    C18 H18 . 0.95 ?
    C19 C20 . 1.511(4) ?
    C20 H20A . 0.98 ?
    C20 H20B . 0.98 ?
    C20 H20C . 0.98 ?
    C21 C22 . 1.506(4) ?
    C22 H22A . 0.98 ?
    C22 H22B . 0.98 ?
    C22 H22C . 0.98 ?
    C31 H31A . 0.98 ?
    C31 H31B . 0.98 ?
    C31 H31C . 0.98 ?
    C41 H41A . 0.98 ?
    C41 H41B . 0.98 ?
    C41 H41C . 0.98 ?
    O50 C51 . 1.395(14) ?
    O50 H50 . 0.84 ?
    C51 C52 . 1.416(9) ?
    C51 H51A . 0.99 ?
    C51 H51B . 0.99 ?
    C52 H52A . 0.98 ?
    C52 H52B . 0.98 ?
    C52 H52C . 0.98 ?
    O60 C61 . 1.392(14) ?
    O60 H60 . 0.84 ?
    C61 C62 . 1.420(9) ?
    C61 H61A . 0.99 ?
    C61 H61B . 0.99 ?
    C62 H62A . 0.98 ?
    C62 H62B . 0.98 ?
    C62 H62C . 0.98 ?
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
    O1 Zn1 N2 . . 104.04(9) y
    O1 Zn1 O3 . . 141.51(9) y
    N2 Zn1 O3 . . 109.90(8) y
    O1 Zn1 N3 . . 111.77(9) y
    N2 Zn1 N3 . . 77.63(7) y
    O3 Zn1 N3 . . 93.07(8) y
    O1 Zn1 O4 . . 99.61(10) y
    N2 Zn1 O4 . . 97.70(8) y
    O3 Zn1 O4 . . 58.83(9) n
    N3 Zn1 O4 . . 148.52(8) y
    O1 Zn1 O2 . . 59.05(8) n
    N2 Zn1 O2 . . 152.59(7) y
    O3 Zn1 O2 . . 94.27(8) y
    N3 Zn1 O2 . . 88.67(8) y
    O4 Zn1 O2 . . 106.02(8) y
    O1 Zn1 C19 . . 29.95(9) ?
    N2 Zn1 C19 . . 131.32(10) ?
    O3 Zn1 C19 . . 118.65(10) ?
    N3 Zn1 C19 . . 102.18(9) ?
    O4 Zn1 C19 . . 103.89(10) ?
    O2 Zn1 C19 . . 29.12(8) ?
    O1 Zn1 C21 . . 122.97(11) ?
    N2 Zn1 C21 . . 105.61(9) ?
    O3 Zn1 C21 . . 29.63(10) ?
    N3 Zn1 C21 . . 121.50(10) ?
    O4 Zn1 C21 . . 29.20(9) ?
    O2 Zn1 C21 . . 101.80(9) ?
    C19 Zn1 C21 . . 114.48(10) ?
    C19 O1 Zn1 . . 97.78(18) ?
    C19 O2 Zn1 . . 82.36(19) ?
    C21 O3 Zn1 . . 95.5(2) ?
    C21 O4 Zn1 . . 86.1(2) ?
    C7 N1 C6 . . 106.41(19) ?
    C7 N1 C13 . . 130.0(2) ?
    C6 N1 C13 . . 123.4(2) ?
    C7 N2 C1 . . 106.3(2) ?
    C7 N2 Zn1 . . 114.58(15) ?
    C1 N2 Zn1 . . 135.73(16) ?
    C12 N3 C8 . . 118.9(2) ?
    C12 N3 Zn1 . . 124.78(17) ?
    C8 N3 Zn1 . . 115.32(15) ?
    C14 N4 C18 . . 116.6(2) ?
    C6 C1 N2 . . 108.5(2) ?
    C6 C1 C2 . . 121.0(2) ?
    N2 C1 C2 . . 130.5(2) ?
    C3 C2 C1 . . 118.1(3) ?
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C2 C3 C4 . . 120.6(2) ?
    C2 C3 C31 . . 119.4(3) ?
    C4 C3 C31 . . 120.0(3) ?
    C5 C4 C3 . . 121.4(2) ?
    C5 C4 C41 . . 118.5(3) ?
    C3 C4 C41 . . 120.1(3) ?
    C4 C5 C6 . . 117.4(3) ?
    C4 C5 H5 . . 121.3 ?
    C6 C5 H5 . . 121.3 ?
    N1 C6 C1 . . 106.5(2) ?
    N1 C6 C5 . . 132.0(2) ?
    C1 C6 C5 . . 121.5(2) ?
    N2 C7 N1 . . 112.3(2) ?
    N2 C7 C8 . . 118.7(2) ?
    N1 C7 C8 . . 128.9(2) ?
    N3 C8 C9 . . 121.9(2) ?
    N3 C8 C7 . . 111.4(2) ?
    C9 C8 C7 . . 126.6(2) ?
    C8 C9 C10 . . 118.1(2) ?
    C8 C9 H9 . . 120.9 ?
    C10 C9 H9 . . 120.9 ?
    C11 C10 C9 . . 120.0(2) ?
    C11 C10 H10 . . 120.0 ?
    C9 C10 H10 . . 120.0 ?
    C10 C11 C12 . . 118.2(2) ?
    C10 C11 H11 . . 120.9 ?
    C12 C11 H11 . . 120.9 ?
    N3 C12 C11 . . 122.8(3) ?
    N3 C12 H12 . . 118.6 ?
    C11 C12 H12 . . 118.6 ?
    N1 C13 C14 . . 112.28(18) ?
    N1 C13 H12A . . 109.1 ?
    C14 C13 H12A . . 109.1 ?
    N1 C13 H13B . . 109.1 ?
    C14 C13 H13B . . 109.1 ?
    H12A C13 H13B . . 107.9 ?
    N4 C14 C15 . . 122.9(2) ?
    N4 C14 C13 . . 116.1(2) ?
    C15 C14 C13 . . 121.0(2) ?
    C14 C15 C16 . . 118.9(3) ?
    C14 C15 H15 . . 120.6 ?
    C16 C15 H15 . . 120.6 ?
    C17 C16 C15 . . 119.1(3) ?
    C17 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    C16 C17 C18 . . 118.2(3) ?
    C16 C17 H17 . . 120.9 ?
    C18 C17 H17 . . 120.9 ?
    N4 C18 C17 . . 124.3(3) ?
    N4 C18 H18 . . 117.8 ?
    C17 C18 H18 . . 117.8 ?
    O2 C19 O1 . . 120.7(3) ?
    O2 C19 C20 . . 120.6(3) ?
    O1 C19 C20 . . 118.7(3) ?
    O2 C19 Zn1 . . 68.52(17) ?
    O1 C19 Zn1 . . 52.27(14) ?
    C20 C19 Zn1 . . 170.3(3) ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O4 C21 O3 . . 119.5(3) ?
    O4 C21 C22 . . 122.5(4) ?
    O3 C21 C22 . . 117.9(3) ?
    O4 C21 Zn1 . . 64.66(18) ?
    O3 C21 Zn1 . . 54.87(15) ?
    C22 C21 Zn1 . . 172.8(3) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C3 C31 H31A . . 109.5 ?
    C3 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C3 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C4 C41 H41A . . 109.5 ?
    C4 C41 H41B . . 109.5 ?
    H41A C41 H41B . . 109.5 ?
    C4 C41 H41C . . 109.5 ?
    H41A C41 H41C . . 109.5 ?
    H41B C41 H41C . . 109.5 ?
    C51 O50 H50 . . 109.5 ?
    O50 C51 C52 . . 111.8(14) ?
    O50 C51 H51A . . 109.3 ?
    C52 C51 H51A . . 109.3 ?
    O50 C51 H51B . . 109.3 ?
    C52 C51 H51B . . 109.3 ?
    H51A C51 H51B . . 107.9 ?
    C51 C52 H52A . . 109.5 ?
    C51 C52 H52B . . 109.5 ?
    H52A C52 H52B . . 109.5 ?
    C51 C52 H52C . . 109.5 ?
    H52A C52 H52C . . 109.5 ?
    H52B C52 H52C . . 109.5 ?
    C61 O60 H60 . . 109.5 ?
    O60 C61 C62 . . 114.1(16) ?
    O60 C61 H61A . . 108.7 ?
    C62 C61 H61A . . 108.7 ?
    O60 C61 H61B . . 108.7 ?
    C62 C61 H61B . . 108.7 ?
    H61A C61 H61B . . 107.6 ?
    C61 C62 H62A . . 109.5 ?
    C61 C62 H62B . . 109.5 ?
    H62A C62 H62B . . 109.5 ?
    C61 C62 H62C . . 109.5 ?
    H62A C62 H62C . . 109.5 ?
    H62B C62 H62C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 N2 C1 C6 . . . . 0.2(2) ?
    Zn1 N2 C1 C6 . . . . -156.77(17) ?
    C7 N2 C1 C2 . . . . -179.0(2) ?
    Zn1 N2 C1 C2 . . . . 24.0(4) ?
    C6 C1 C2 C3 . . . . 1.4(3) ?
    N2 C1 C2 C3 . . . . -179.5(2) ?
    C1 C2 C3 C4 . . . . -0.5(3) ?
    C1 C2 C3 C31 . . . . 178.8(2) ?
    C2 C3 C4 C5 . . . . -0.1(4) ?
    C31 C3 C4 C5 . . . . -179.4(2) ?
    C2 C3 C4 C41 . . . . -178.4(2) ?
    C31 C3 C4 C41 . . . . 2.3(3) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C41 C4 C5 C6 . . . . 178.2(2) ?
    C7 N1 C6 C1 . . . . 0.1(2) ?
    C13 N1 C6 C1 . . . . 175.37(19) ?
    C7 N1 C6 C5 . . . . -179.0(2) ?
    C13 N1 C6 C5 . . . . -3.7(4) ?
    N2 C1 C6 N1 . . . . -0.2(2) ?
    C2 C1 C6 N1 . . . . 179.14(19) ?
    N2 C1 C6 C5 . . . . 179.0(2) ?
    C2 C1 C6 C5 . . . . -1.7(3) ?
    C4 C5 C6 N1 . . . . 179.9(2) ?
    C4 C5 C6 C1 . . . . 0.9(3) ?
    C1 N2 C7 N1 . . . . -0.1(2) ?
    Zn1 N2 C7 N1 . . . . 162.37(14) ?
    C1 N2 C7 C8 . . . . -177.37(19) ?
    Zn1 N2 C7 C8 . . . . -14.9(3) ?
    C6 N1 C7 N2 . . . . 0.1(2) ?
    C13 N1 C7 N2 . . . . -174.8(2) ?
    C6 N1 C7 C8 . . . . 176.9(2) ?
    C13 N1 C7 C8 . . . . 2.0(4) ?
    C12 N3 C8 C9 . . . . -2.7(3) ?
    Zn1 N3 C8 C9 . . . . 166.30(17) ?
    C12 N3 C8 C7 . . . . 179.6(2) ?
    Zn1 N3 C8 C7 . . . . -11.4(2) ?
    N2 C7 C8 N3 . . . . 17.6(3) ?
    N1 C7 C8 N3 . . . . -159.1(2) ?
    N2 C7 C8 C9 . . . . -160.0(2) ?
    N1 C7 C8 C9 . . . . 23.3(4) ?
    N3 C8 C9 C10 . . . . 3.5(3) ?
    C7 C8 C9 C10 . . . . -179.3(2) ?
    C8 C9 C10 C11 . . . . -1.3(4) ?
    C9 C10 C11 C12 . . . . -1.5(4) ?
    C8 N3 C12 C11 . . . . -0.3(3) ?
    Zn1 N3 C12 C11 . . . . -168.15(18) ?
    C10 C11 C12 N3 . . . . 2.3(4) ?
    C7 N1 C13 C14 . . . . -105.8(3) ?
    C6 N1 C13 C14 . . . . 80.1(3) ?
    C18 N4 C14 C15 . . . . -0.1(4) ?
    C18 N4 C14 C13 . . . . 178.7(2) ?
    N1 C13 C14 N4 . . . . 59.4(3) ?
    N1 C13 C14 C15 . . . . -121.8(3) ?
    N4 C14 C15 C16 . . . . -0.9(4) ?
    C13 C14 C15 C16 . . . . -179.7(3) ?
    C14 C15 C16 C17 . . . . 0.9(5) ?
    C15 C16 C17 C18 . . . . 0.2(5) ?
    C14 N4 C18 C17 . . . . 1.2(4) ?
    C16 C17 C18 N4 . . . . -1.3(5) ?
    Zn1 O2 C19 O1 . . . . 3.0(3) ?
    Zn1 O2 C19 C20 . . . . -176.5(3) ?
    Zn1 O1 C19 O2 . . . . -3.5(4) ?
    Zn1 O1 C19 C20 . . . . 175.9(3) ?
    Zn1 O4 C21 O3 . . . . -0.5(3) ?
    Zn1 O4 C21 C22 . . . . -179.6(3) ?
    Zn1 O3 C21 O4 . . . . 0.6(3) ?
    Zn1 O3 C21 C22 . . . . 179.7(3) ?
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
    C9 H9 O50 . 0.95 2.56 3.167(15) 122.1 y
    C9 H9 O60 . 0.95 2.40 3.125(14) 133.1 ?
    C15 H15 O1 3_767 0.95 2.40 3.333(3) 167.0 y
    C17 H17 O2 4_576 0.95 2.58 3.325(4) 135.8 y
    O50 H50 O3 2_646 0.84 1.91 2.749(15) 173.1 y
    C10 H10 O3 2_646 0.95 2.53 3.414(4) 154.5 y
