##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-11-22
_journal_date_accepted     2006-11-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      1
_journal_page_first     m15
_journal_page_last     m16
_journal_paper_category     EM
_journal_coeditor_code     CI2231
_publ_contact_author_name     'Dr. Seik Weng Ng'
_publ_contact_author_address
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Bis[(1H-benzimidazol-2-yl)methanol-κ²N,O](nitrato-\
κ²O,O')zinc(II) nitrate monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhou, Yan-Ling'
;
Department of Chemistry
Guangxi Normal University
Guilin 541000
Guangxi
People's Republic of China
;
    'Zeng, Ming-Hua'
;
Department of Chemistry
Guangxi Normal University
Guilin 541000
Guangxi
People's Republic of China
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis[(1H-benzimidazol-2-yl)methanol-κ²N,O](nitrato-κ²O,O')zinc(II)
nitrate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N5 O5 Zn +, N O3 -, H2 O'
_chemical_formula_sum     'C16 H18 N6 O9 Zn'
_chemical_formula_iupac     '[Zn (N O3) (C8 H8 N2 O)2] N O3, H2 O'
_chemical_formula_weight     503.73
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.2287(8)
_cell_length_b     9.6745(9)
_cell_length_c     13.5420(10)
_cell_angle_alpha     81.506(2)
_cell_angle_beta     80.678(2)
_cell_angle_gamma     69.867(2)
_cell_volume     993.89(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1775
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     25.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     'Pale yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.683
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     516
_exptl_absorpt_coefficient_mu     1.301
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.781
_exptl_absorpt_correction_T_max     0.903
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX2 area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5025
_diffrn_reflns_av_R_equivalents     0.020
_diffrn_reflns_av_sigmaI/netI     0.044
_diffrn_reflns_theta_min     1.5
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.98
_diffrn_measured_fraction_theta_full     0.98
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3444
_reflns_number_gt     2947
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.050
_refine_ls_R_factor_gt     0.042
_refine_ls_wR_factor_gt     0.101
_refine_ls_wR_factor_ref     0.114
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.06
_refine_ls_number_reflns     3444
_refine_ls_number_parameters     313
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0636P)²+0.1377P] 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     0.42
_refine_diff_density_min     -0.38
_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, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     SHELXL97
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_disorder_assembly
    _atom_site_disorder_group
    Zn Zn1 0.63068(5) 0.28762(4) 0.71867(3) 0.03887(16) Uani d . 1 . .
    O O1 0.7129(4) 0.4602(3) 0.61315(18) 0.0498(6) Uani d D 1 . .
    O O2 0.8274(4) 0.1249(3) 0.80316(19) 0.0552(7) Uani d D 1 . .
    O O3 0.3507(3) 0.3877(3) 0.70619(18) 0.0528(6) Uani d . 1 . .
    O O4 0.4400(4) 0.1801(3) 0.7952(2) 0.0597(7) Uani d . 1 . .
    O O5 0.1635(4) 0.2852(4) 0.7842(2) 0.0794(9) Uani d . 1 . .
    O O6 1.0456(4) 0.1810(3) 0.23550(19) 0.0685(8) Uani d . 1 . .
    O O7 0.9411(4) 0.3797(3) 0.1372(2) 0.0639(8) Uani d . 1 . .
    O O8 1.0147(4) 0.1678(3) 0.0834(2) 0.0733(9) Uani d . 1 . .
    O O1w 0.9389(4) 0.5498(4) 0.6807(2) 0.0660(8) Uani d D 1 . .
    N N1 0.7096(3) 0.1969(3) 0.58860(18) 0.0362(6) Uani d . 1 . .
    N N2 0.8324(4) 0.1899(3) 0.4307(2) 0.0428(7) Uani d D 1 . .
    N N3 0.6455(3) 0.3992(3) 0.82755(18) 0.0364(6) Uani d . 1 . .
    N N4 0.7730(4) 0.4208(3) 0.9528(2) 0.0436(7) Uani d D 1 . .
    N N5 0.3140(4) 0.2837(4) 0.7627(2) 0.0518(8) Uani d . 1 . .
    N N6 0.9990(4) 0.2446(4) 0.1516(2) 0.0480(7) Uani d . 1 . .
    C C1 0.7183(4) 0.0643(4) 0.5560(2) 0.0366(7) Uani d . 1 . .
    C C2 0.6608(4) -0.0497(4) 0.6050(3) 0.0428(8) Uani d . 1 . .
    H H2 0.6090 -0.0474 0.6714 0.051 Uiso calc R 1 . .
    C C3 0.6835(5) -0.1657(4) 0.5515(3) 0.0504(9) Uani d . 1 . .
    H H3 0.6439 -0.2427 0.5821 0.060 Uiso calc R 1 . .
    C C4 0.7641(5) -0.1721(4) 0.4527(3) 0.0531(9) Uani d . 1 . .
    H H4 0.7782 -0.2538 0.4195 0.064 Uiso calc R 1 . .
    C C5 0.8235(5) -0.0603(4) 0.4030(3) 0.0482(9) Uani d . 1 . .
    H H5 0.8783 -0.0647 0.3373 0.058 Uiso calc R 1 . .
    C C6 0.7972(4) 0.0583(4) 0.4562(2) 0.0395(8) Uani d . 1 . .
    C C7 0.7782(4) 0.2673(4) 0.5116(2) 0.0378(7) Uani d . 1 . .
    C C8 0.7888(5) 0.4168(4) 0.5156(3) 0.0496(9) Uani d . 1 . .
    H H8A 0.9094 0.4138 0.5039 0.059 Uiso calc R 1 . .
    H H8B 0.7258 0.4867 0.4645 0.059 Uiso calc R 1 . .
    C C9 0.5821(4) 0.5475(4) 0.8472(2) 0.0377(7) Uani d . 1 . .
    C C10 0.4643(5) 0.6696(4) 0.8017(3) 0.0469(9) Uani d . 1 . .
    H H10 0.4082 0.6612 0.7496 0.056 Uiso calc R 1 . .
    C C11 0.4330(5) 0.8044(4) 0.8362(3) 0.0564(10) Uani d . 1 . .
    H H11 0.3544 0.8886 0.8068 0.068 Uiso calc R 1 . .
    C C12 0.5167(6) 0.8169(4) 0.9142(3) 0.0610(11) Uani d . 1 . .
    H H12 0.4936 0.9100 0.9349 0.073 Uiso calc R 1 . .
    C C13 0.6315(5) 0.6975(4) 0.9613(3) 0.0539(10) Uani d . 1 . .
    H H13 0.6855 0.7069 1.0140 0.065 Uiso calc R 1 . .
    C C14 0.6637(4) 0.5609(4) 0.9267(2) 0.0417(8) Uani d . 1 . .
    C C15 0.7580(4) 0.3290(4) 0.8921(2) 0.0389(7) Uani d . 1 . .
    C C16 0.8541(5) 0.1691(4) 0.8933(2) 0.0460(8) Uani d . 1 . .
    H H16A 0.9773 0.1497 0.8955 0.055 Uiso calc R 1 . .
    H H16B 0.8101 0.1154 0.9517 0.055 Uiso calc R 1 . .
    H H1O 0.782(5) 0.485(6) 0.641(4) 0.11(2) Uiso d D 1 . .
    H H2O 0.855(5) 0.0325(12) 0.808(3) 0.056(12) Uiso d D 1 . .
    H H1W1 0.996(6) 0.478(4) 0.719(3) 0.084(17) Uiso d D 1 . .
    H H1W2 0.900(6) 0.628(3) 0.711(3) 0.090(19) Uiso d D 1 . .
    H H2N 0.881(6) 0.218(5) 0.3748(19) 0.088(16) Uiso d D 1 . .
    H H4N 0.837(4) 0.393(4) 1.0003(19) 0.048(10) Uiso d D 1 . .
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 . 2.246(3) yes
    Zn1 O2 . 2.173(3) yes
    Zn1 O3 . 2.195(2) yes
    Zn1 O4 . 2.213(3) yes
    Zn1 N1 . 1.997(2) yes
    Zn1 N3 . 1.993(3) yes
    O1 C8 . 1.424(4) ?
    O1 H1O . 0.850(10)
                     ?
    O2 C16 . 1.424(4) ?
    O2 H2O . 0.840(10)
                     ?
    O3 N5 . 1.263(4) ?
    O4 N5 . 1.255(4) ?
    O5 N5 . 1.221(4) ?
    O6 N6 . 1.261(4) ?
    O7 N6 . 1.224(4) ?
    O8 N6 . 1.233(4) ?
    O1w H1W1 . 0.850(10)
                       ?
    O1w H1W2 . 0.850(10)
                       ?
    N1 C7 . 1.316(4) ?
    N1 C1 . 1.393(4) ?
    N2 C7 . 1.346(4) ?
    N2 C6 . 1.385(5) ?
    N2 H2N . 0.850(10)
                     ?
    N3 C15 . 1.318(4) ?
    N3 C9 . 1.398(4) ?
    N4 C15 . 1.343(4) ?
    N4 C14 . 1.376(4) ?
    N4 H4N . 0.850(10)
                     ?
    C1 C2 . 1.386(5) ?
    C1 C6 . 1.403(4) ?
    C2 C3 . 1.368(5) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.394(5) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.380(5) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.380(5) ?
    C5 H5 . 0.93 ?
    C7 C8 . 1.489(5) ?
    C8 H8A . 0.97 ?
    C8 H8B . 0.97 ?
    C9 C10 . 1.380(5) ?
    C9 C14 . 1.401(5) ?
    C10 C11 . 1.376(5) ?
    C10 H10 . 0.93 ?
    C11 C12 . 1.392(6) ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.363(6) ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.392(5) ?
    C13 H13 . 0.93 ?
    C15 C16 . 1.474(5) ?
    C16 H16A . 0.97 ?
    C16 H16B . 0.97 ?
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 O2 . . 117.30(10)
                           yes
    O1 Zn1 O3 . . 96.20(10)
                          yes
    O1 Zn1 O4 . . 154.10(10)
                           yes
    O1 Zn1 N1 . . 76.20(10)
                          yes
    O1 Zn1 N3 . . 85.30(10)
                          yes
    O2 Zn1 O3 . . 145.40(10)
                           yes
    O2 Zn1 O4 . . 88.60(10)
                          yes
    O2 Zn1 N1 . . 96.70(10)
                          yes
    O2 Zn1 N3 . . 77.10(10)
                          yes
    O3 Zn1 O4 . . 58.10(10)
                          yes
    O3 Zn1 N1 . . 99.50(10)
                          yes
    O3 Zn1 N3 . . 98.80(10)
                          yes
    O4 Zn1 N1 . . 103.10(10)
                           yes
    O4 Zn1 N3 . . 100.80(10)
                           yes
    N1 Zn1 N3 . . 155.20(10)
                           yes
    C8 O1 Zn1 . . 114.9(2) ?
    C8 O1 H1O . . 110(4) ?
    Zn1 O1 H1O . . 108(4) ?
    C16 O2 Zn1 . . 115.8(2) ?
    C16 O2 H2O . . 110(3) ?
    Zn1 O2 H2O . . 128(3) ?
    N5 O3 Zn1 . . 93.0(2) ?
    N5 O4 Zn1 . . 92.4(2) ?
    H1W1 O1w H1W2 . . 110(5) ?
    C7 N1 C1 . . 106.0(3) ?
    C7 N1 Zn1 . . 119.0(2) ?
    C1 N1 Zn1 . . 134.9(2) ?
    C7 N2 C6 . . 107.8(3) ?
    C7 N2 H2N . . 125(3) ?
    C6 N2 H2N . . 127(3) ?
    C15 N3 C9 . . 106.4(3) ?
    C15 N3 Zn1 . . 117.5(2) ?
    C9 N3 Zn1 . . 135.2(2) ?
    C15 N4 C14 . . 108.2(3) ?
    C15 N4 H4N . . 124(2) ?
    C14 N4 H4N . . 128(2) ?
    O5 N5 O4 . . 122.3(4) ?
    O5 N5 O3 . . 121.3(4) ?
    O4 N5 O3 . . 116.5(3) ?
    O7 N6 O8 . . 120.4(3) ?
    O7 N6 O6 . . 121.1(3) ?
    O8 N6 O6 . . 118.5(3) ?
    C2 C1 N1 . . 130.7(3) ?
    C2 C1 C6 . . 120.6(3) ?
    N1 C1 C6 . . 108.7(3) ?
    C3 C2 C1 . . 117.1(3) ?
    C3 C2 H2 . . 121.4 ?
    C1 C2 H2 . . 121.4 ?
    C2 C3 C4 . . 122.1(4) ?
    C2 C3 H3 . . 119.0 ?
    C4 C3 H3 . . 119.0 ?
    C5 C4 C3 . . 121.6(3) ?
    C5 C4 H4 . . 119.2 ?
    C3 C4 H4 . . 119.2 ?
    C4 C5 C6 . . 116.4(3) ?
    C4 C5 H5 . . 121.8 ?
    C6 C5 H5 . . 121.8 ?
    C5 C6 N2 . . 132.6(3) ?
    C5 C6 C1 . . 122.2(3) ?
    N2 C6 C1 . . 105.2(3) ?
    N1 C7 N2 . . 112.3(3) ?
    N1 C7 C8 . . 122.5(3) ?
    N2 C7 C8 . . 125.2(3) ?
    O1 C8 C7 . . 107.1(3) ?
    O1 C8 H8A . . 110.3 ?
    C7 C8 H8A . . 110.3 ?
    O1 C8 H8B . . 110.3 ?
    C7 C8 H8B . . 110.3 ?
    H8A C8 H8B . . 108.5 ?
    C10 C9 N3 . . 131.3(3) ?
    C10 C9 C14 . . 120.8(3) ?
    N3 C9 C14 . . 107.9(3) ?
    C11 C10 C9 . . 117.5(3) ?
    C11 C10 H10 . . 121.2 ?
    C9 C10 H10 . . 121.2 ?
    C10 C11 C12 . . 121.2(4) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C13 C12 C11 . . 122.3(4) ?
    C13 C12 H12 . . 118.8 ?
    C11 C12 H12 . . 118.8 ?
    C12 C13 C14 . . 116.7(4) ?
    C12 C13 H13 . . 121.6 ?
    C14 C13 H13 . . 121.6 ?
    N4 C14 C13 . . 132.9(3) ?
    N4 C14 C9 . . 105.7(3) ?
    C13 C14 C9 . . 121.4(3) ?
    N3 C15 N4 . . 111.8(3) ?
    N3 C15 C16 . . 122.1(3) ?
    N4 C15 C16 . . 126.1(3) ?
    O2 C16 C15 . . 106.3(3) ?
    O2 C16 H16A . . 110.5 ?
    C15 C16 H16A . . 110.5 ?
    O2 C16 H16B . . 110.5 ?
    C15 C16 H16B . . 110.5 ?
    H16A C16 H16B . . 108.7 ?
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
    N3 Zn1 O1 C8 . . . . 158.5(3) ?
    N1 Zn1 O1 C8 . . . . -4.8(2) ?
    O2 Zn1 O1 C8 . . . . 85.7(3) ?
    O3 Zn1 O1 C8 . . . . -103.1(2) ?
    O4 Zn1 O1 C8 . . . . -96.4(3) ?
    N3 Zn1 O2 C16 . . . . 6.1(2) ?
    N1 Zn1 O2 C16 . . . . 161.7(2) ?
    O3 Zn1 O2 C16 . . . . -80.7(3) ?
    O4 Zn1 O2 C16 . . . . -95.3(2) ?
    O1 Zn1 O2 C16 . . . . 83.8(3) ?
    N3 Zn1 O3 N5 . . . . -96.53(19) ?
    N1 Zn1 O3 N5 . . . . 100.28(19) ?
    O2 Zn1 O3 N5 . . . . -16.6(3) ?
    O4 Zn1 O3 N5 . . . . 0.76(18) ?
    O1 Zn1 O3 N5 . . . . 177.30(18) ?
    N3 Zn1 O4 N5 . . . . 93.0(2) ?
    N1 Zn1 O4 N5 . . . . -94.0(2) ?
    O2 Zn1 O4 N5 . . . . 169.5(2) ?
    O3 Zn1 O4 N5 . . . . -0.76(18) ?
    O1 Zn1 O4 N5 . . . . -8.7(3) ?
    N3 Zn1 N1 C7 . . . . -38.4(4) ?
    O2 Zn1 N1 C7 . . . . -111.9(2) ?
    O3 Zn1 N1 C7 . . . . 98.7(2) ?
    O4 Zn1 N1 C7 . . . . 158.0(2) ?
    O1 Zn1 N1 C7 . . . . 4.6(2) ?
    N3 Zn1 N1 C1 . . . . 138.2(3) ?
    O2 Zn1 N1 C1 . . . . 64.7(3) ?
    O3 Zn1 N1 C1 . . . . -84.7(3) ?
    O4 Zn1 N1 C1 . . . . -25.4(3) ?
    O1 Zn1 N1 C1 . . . . -178.8(3) ?
    N1 Zn1 N3 C15 . . . . -77.0(3) ?
    O2 Zn1 N3 C15 . . . . 0.8(2) ?
    O3 Zn1 N3 C15 . . . . 145.8(2) ?
    O4 Zn1 N3 C15 . . . . 86.8(2) ?
    O1 Zn1 N3 C15 . . . . -118.6(2) ?
    N1 Zn1 N3 C9 . . . . 91.3(4) ?
    O2 Zn1 N3 C9 . . . . 169.1(3) ?
    O3 Zn1 N3 C9 . . . . -45.9(3) ?
    O4 Zn1 N3 C9 . . . . -104.9(3) ?
    O1 Zn1 N3 C9 . . . . 49.6(3) ?
    Zn1 O4 N5 O5 . . . . -178.5(3) ?
    Zn1 O4 N5 O3 . . . . 1.3(3) ?
    Zn1 O3 N5 O5 . . . . 178.5(3) ?
    Zn1 O3 N5 O4 . . . . -1.3(3) ?
    C7 N1 C1 C2 . . . . -178.0(3) ?
    Zn1 N1 C1 C2 . . . . 5.1(5) ?
    C7 N1 C1 C6 . . . . 0.6(3) ?
    Zn1 N1 C1 C6 . . . . -176.3(2) ?
    N1 C1 C2 C3 . . . . 178.0(3) ?
    C6 C1 C2 C3 . . . . -0.4(5) ?
    C1 C2 C3 C4 . . . . 1.4(5) ?
    C2 C3 C4 C5 . . . . -0.9(6) ?
    C3 C4 C5 C6 . . . . -0.6(5) ?
    C4 C5 C6 N2 . . . . -177.4(3) ?
    C4 C5 C6 C1 . . . . 1.5(5) ?
    C7 N2 C6 C5 . . . . 179.5(3) ?
    C7 N2 C6 C1 . . . . 0.4(4) ?
    C2 C1 C6 C5 . . . . -1.0(5) ?
    N1 C1 C6 C5 . . . . -179.8(3) ?
    C2 C1 C6 N2 . . . . 178.1(3) ?
    N1 C1 C6 N2 . . . . -0.6(4) ?
    C1 N1 C7 N2 . . . . -0.3(4) ?
    Zn1 N1 C7 N2 . . . . 177.2(2) ?
    C1 N1 C7 C8 . . . . 178.4(3) ?
    Zn1 N1 C7 C8 . . . . -4.1(4) ?
    C6 N2 C7 N1 . . . . -0.1(4) ?
    C6 N2 C7 C8 . . . . -178.7(3) ?
    Zn1 O1 C8 C7 . . . . 4.0(4) ?
    N1 C7 C8 O1 . . . . -0.3(5) ?
    N2 C7 C8 O1 . . . . 178.2(3) ?
    C15 N3 C9 C10 . . . . 178.9(3) ?
    Zn1 N3 C9 C10 . . . . 9.7(5) ?
    C15 N3 C9 C14 . . . . 0.1(3) ?
    Zn1 N3 C9 C14 . . . . -169.1(2) ?
    N3 C9 C10 C11 . . . . -177.5(3) ?
    C14 C9 C10 C11 . . . . 1.1(5) ?
    C9 C10 C11 C12 . . . . -0.1(5) ?
    C10 C11 C12 C13 . . . . -0.9(6) ?
    C11 C12 C13 C14 . . . . 0.9(6) ?
    C15 N4 C14 C13 . . . . -177.4(4) ?
    C15 N4 C14 C9 . . . . 0.2(4) ?
    C12 C13 C14 N4 . . . . 177.4(4) ?
    C12 C13 C14 C9 . . . . 0.1(5) ?
    C10 C9 C14 N4 . . . . -179.1(3) ?
    N3 C9 C14 N4 . . . . -0.2(4) ?
    C10 C9 C14 C13 . . . . -1.1(5) ?
    N3 C9 C14 C13 . . . . 177.8(3) ?
    C9 N3 C15 N4 . . . . 0.0(4) ?
    Zn1 N3 C15 N4 . . . . 171.4(2) ?
    C9 N3 C15 C16 . . . . -179.2(3) ?
    Zn1 N3 C15 C16 . . . . -7.8(4) ?
    C14 N4 C15 N3 . . . . -0.1(4) ?
    C14 N4 C15 C16 . . . . 179.1(3) ?
    Zn1 O2 C16 C15 . . . . -10.5(3) ?
    N3 C15 C16 O2 . . . . 12.1(4) ?
    N4 C15 C16 O2 . . . . -167.0(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
    O1 H1O O1w . 0.850(10)
                         1.800(10)
                                 2.635(4) 172(5) yes
    O2 H2O O6 2_756 0.840(10)
                            2.08(2) 2.877(4) 159(4) yes
    O1w H1w1 O5 1_655 0.850(10)
                              2.07(2) 2.908(5) 168(5) yes
    O1w H1w2 O6 2_766 0.850(10)
                              2.29(3) 3.038(5) 148(5) yes
    N2 H2n O6 . 0.850(10)
                        2.14(2) 2.922(4) 154(4) yes
    N4 H4n O7 1_556 0.850(10)
                            2.14(2) 2.959(4) 163(3) yes
