##############################################################################
###                                                                        ###
###        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     'SHELXL97'
_journal_date_recd_electronic     2006-05-30
_journal_date_accepted     2006-06-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      7
_journal_page_first     m1535
_journal_page_last     m1537
_journal_paper_category     EM
_journal_coeditor_code     HB2075
_publ_contact_author_name     'Guang-Bo Che'
_publ_contact_author_address
;
Department of Chemistry
Jilin Normal University
Siping 136000
People's Republic of China
;
_publ_contact_author_email     guangbochejl@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
A new dinuclear ZnII compound with a 1,4-benzenedicarboxylate bridge
;
loop_
    _publ_author_name
    _publ_author_address
    'Guang-Bo Che'
;
Department of Chemistry
Jilin Normal University
Siping 136000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
μ₂-1,4-benzenedicarboxylate-κ²O,O'[bis[aquachloro-4-(1H-1,3,7,8-
tetraazacyclopenta[l]phenanthren-2-yl)phenol-κ²N,N']zinc(II)] dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C46 H32 Cl2 N8 O8 Zn2 , 2H2 O'
_chemical_formula_sum     'C46 H36 Cl2 N8 O10 Zn2'
_chemical_formula_iupac
                          '[Zn2 Cl2 (C8 H4 O4) (C19 H12 N4 O)2 (H2 O)2] , 2H2 O'
_chemical_formula_weight     1062.47
_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     9.1608(18)
_cell_length_b     9.4769(19)
_cell_length_c     13.334(3)
_cell_angle_alpha     109.24(3)
_cell_angle_beta     90.66(3)
_cell_angle_gamma     104.02(3)
_cell_volume     1055.1(5)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     7257
_cell_measurement_theta_min     3.25
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.672
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     542
_exptl_absorpt_coefficient_mu     1.337
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.684
_exptl_absorpt_correction_T_max     0.758
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     292(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     10429
_diffrn_reflns_av_R_equivalents     0.0587
_diffrn_reflns_av_sigmaI/netI     0.0820
_diffrn_reflns_theta_min     3.25
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     none
_diffrn_standards_interval_count     none
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     4780
_reflns_number_gt     3065
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0967
_refine_ls_R_factor_gt     0.0515
_refine_ls_wR_factor_gt     0.0970
_refine_ls_wR_factor_ref     0.1127
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     4780
_refine_ls_number_parameters     321
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0392P)²+0.7847P] 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     0.735
_refine_diff_density_min     -0.428
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'PROCESS-AUTO'
_computing_data_reduction     'PROCESS-AUTO'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL-Plus (Sheldrick, 1990)'
_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
    C C1 0.9669(4) 0.7960(5) 0.3295(3) 0.0395(10) Uani d . 1 . .
    H H1 1.0457 0.7649 0.3531 0.047 Uiso calc R 1 . .
    C C2 1.0013(5) 0.9286(5) 0.3025(3) 0.0415(11) Uani d . 1 . .
    H H2 1.1014 0.9848 0.3082 0.050 Uiso calc R 1 . .
    C C3 0.8875(4) 0.9768(5) 0.2673(3) 0.0362(10) Uani d . 1 . .
    H H3 0.9090 1.0664 0.2498 0.043 Uiso calc R 1 . .
    C C4 0.7374(4) 0.8882(4) 0.2580(3) 0.0255(8) Uani d . 1 . .
    C C5 0.7119(4) 0.7549(4) 0.2870(3) 0.0268(8) Uani d . 1 . .
    C C6 0.5606(4) 0.6583(4) 0.2806(3) 0.0244(8) Uani d . 1 . .
    C C7 0.4110(4) 0.4480(5) 0.3136(3) 0.0319(9) Uani d . 1 . .
    H H7 0.4022 0.3658 0.3385 0.038 Uiso calc R 1 . .
    C C8 0.2801(5) 0.4724(5) 0.2760(3) 0.0344(9) Uani d . 1 . .
    H H8 0.1861 0.4073 0.2760 0.041 Uiso calc R 1 . .
    C C9 0.2908(4) 0.5925(5) 0.2393(3) 0.0313(9) Uani d . 1 . .
    H H9 0.2044 0.6090 0.2128 0.038 Uiso calc R 1 . .
    C C10 0.4336(4) 0.6909(4) 0.2418(3) 0.0254(8) Uani d . 1 . .
    C C11 0.4622(4) 0.8246(4) 0.2106(3) 0.0257(8) Uani d . 1 . .
    C C12 0.6065(4) 0.9177(4) 0.2205(3) 0.0280(8) Uani d . 1 . .
    C C13 0.4428(4) 1.0063(4) 0.1535(3) 0.0303(9) Uani d . 1 . .
    C C14 0.3841(4) 1.1032(4) 0.1065(3) 0.0289(8) Uani d . 1 . .
    C C15 0.2298(5) 1.0816(5) 0.0882(3) 0.0366(9) Uani d . 1 . .
    H H15 0.1635 1.0053 0.1070 0.044 Uiso calc R 1 . .
    C C16 0.1720(5) 1.1704(5) 0.0427(3) 0.0405(10) Uani d . 1 . .
    H H16 0.0680 1.1547 0.0319 0.049 Uiso calc R 1 . .
    C C17 0.2694(5) 1.2830(5) 0.0132(3) 0.0356(9) Uani d . 1 . .
    C C18 0.4241(5) 1.3061(5) 0.0307(3) 0.0356(9) Uani d . 1 . .
    H H18 0.4902 1.3820 0.0114 0.043 Uiso calc R 1 . .
    C C19 0.4805(5) 1.2169(5) 0.0768(3) 0.0335(9) Uani d . 1 . .
    H H19 0.5846 1.2332 0.0881 0.040 Uiso calc R 1 . .
    C C20 0.6948(4) 0.2648(4) 0.4631(3) 0.0298(9) Uani d . 1 . .
    C C21 0.5926(4) 0.1264(4) 0.4807(3) 0.0265(8) Uani d . 1 . .
    C C22 0.4369(4) 0.0984(4) 0.4681(3) 0.0307(9) Uani d . 1 . .
    H H22 0.3940 0.1645 0.4465 0.037 Uiso calc R 1 . .
    C C23 0.3454(4) -0.0261(5) 0.4872(3) 0.0318(9) Uani d . 1 . .
    H H23 0.2409 -0.0435 0.4787 0.038 Uiso calc R 1 . .
    N N1 0.8264(3) 0.7114(4) 0.3231(2) 0.0296(7) Uani d . 1 . .
    N N2 0.5478(3) 0.5374(3) 0.3154(2) 0.0271(7) Uani d . 1 . .
    N N3 0.3606(3) 0.8805(4) 0.1686(2) 0.0299(7) Uani d . 1 . .
    N N4 0.5907(4) 1.0336(4) 0.1846(2) 0.0298(7) Uani d . 1 . .
    H H4 0.6622 1.1100 0.1824 0.036 Uiso calc R 1 . .
    O O1 0.6346(3) 0.3325(3) 0.4135(2) 0.0405(7) Uani d . 1 . .
    O O2 0.8287(3) 0.3067(3) 0.5005(2) 0.0449(8) Uani d . 1 . .
    O O1W 0.8694(4) 0.6100(4) 0.5082(2) 0.0419(8) Uani d . 1 . .
    O O3 0.2213(4) 1.3747(3) -0.0318(2) 0.0481(8) Uani d . 1 . .
    H H3A 0.1285 1.3514 -0.0388 0.072 Uiso calc R 1 . .
    O O2W 0.0842(4) 0.6786(4) 0.0430(3) 0.0604(9) Uani d D 1 . .
    Zn Zn1 0.75014(5) 0.50066(5) 0.35762(4) 0.03021(14) Uani d . 1 . .
    Cl Cl1 0.86655(11) 0.35345(12) 0.22822(8) 0.0415(3) Uani d . 1 . .
    H HW11 0.961(7) 0.641(7) 0.503(4) 0.07(2) Uiso d . 1 . .
    H HW12 0.860(6) 0.527(6) 0.524(4) 0.059(16) Uiso d . 1 . .
    H HW21 0.169(4) 0.733(6) 0.084(3) 0.089 Uiso d D 1 . .
    H HW22 0.121(5) 0.626(6) -0.020(2) 0.089 Uiso d D 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
    Zn1 O1 . 2.049(3) y
    Zn1 O1W . 2.080(3) y
    Zn1 N1 . 2.150(3) y
    Zn1 N2 . 2.072(3) y
    Zn1 Cl1 . 2.2885(14) y
    C1 N1 . 1.327(5) ?
    C1 C2 . 1.385(5) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.370(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.407(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.407(5) ?
    C4 C12 . 1.416(5) ?
    C5 N1 . 1.354(5) ?
    C5 C6 . 1.448(5) ?
    C6 N2 . 1.352(4) ?
    C6 C10 . 1.407(5) ?
    C7 N2 . 1.327(5) ?
    C7 C8 . 1.392(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.363(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.403(5) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.427(5) ?
    C11 N3 . 1.372(4) ?
    C11 C12 . 1.378(5) ?
    C12 N4 . 1.370(4) ?
    C13 N3 . 1.325(5) ?
    C13 N4 . 1.349(5) ?
    C13 C14 . 1.462(5) ?
    C14 C15 . 1.385(5) ?
    C14 C19 . 1.388(5) ?
    C15 C16 . 1.379(5) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.382(6) ?
    C16 H16 . 0.9300 ?
    C17 O3 . 1.354(4) ?
    C17 C18 . 1.386(6) ?
    C18 C19 . 1.381(5) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
    C20 O2 . 1.237(4) y
    C20 O1 . 1.263(4) y
    C20 C21 . 1.505(5) ?
    C21 C22 . 1.384(5) ?
    C21 C23 2_656 1.390(5) ?
    C22 C23 . 1.373(5) ?
    C22 H22 . 0.9300 ?
    C23 C21 2_656 1.390(5) ?
    C23 H23 . 0.9300 ?
    N4 H4 . 0.8600 ?
    O1W HW11 . 0.83(6) ?
    O1W HW12 . 0.87(5) ?
    O3 H3A . 0.8200 ?
    O2W HW21 . 0.88(4) ?
    O2W HW22 . 0.941(19) ?
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 C1 C2 . . 122.8(4) ?
    N1 C1 H1 . . 118.6 ?
    C2 C1 H1 . . 118.6 ?
    C3 C2 C1 . . 119.8(4) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 118.8(4) ?
    C2 C3 H3 . . 120.6 ?
    C4 C3 H3 . . 120.6 ?
    C3 C4 C5 . . 117.9(3) ?
    C3 C4 C12 . . 126.6(3) ?
    C5 C4 C12 . . 115.5(3) ?
    N1 C5 C4 . . 122.0(3) ?
    N1 C5 C6 . . 116.7(3) ?
    C4 C5 C6 . . 121.3(3) ?
    N2 C6 C10 . . 122.0(3) ?
    N2 C6 C5 . . 116.6(3) ?
    C10 C6 C5 . . 121.4(3) ?
    N2 C7 C8 . . 122.7(4) ?
    N2 C7 H7 . . 118.7 ?
    C8 C7 H7 . . 118.7 ?
    C9 C8 C7 . . 119.5(4) ?
    C9 C8 H8 . . 120.3 ?
    C7 C8 H8 . . 120.3 ?
    C8 C9 C10 . . 119.3(4) ?
    C8 C9 H9 . . 120.4 ?
    C10 C9 H9 . . 120.4 ?
    C9 C10 C6 . . 117.8(3) ?
    C9 C10 C11 . . 125.7(3) ?
    C6 C10 C11 . . 116.4(3) ?
    N3 C11 C12 . . 110.3(3) ?
    N3 C11 C10 . . 128.4(3) ?
    C12 C11 C10 . . 121.3(3) ?
    N4 C12 C11 . . 105.1(3) ?
    N4 C12 C4 . . 130.7(3) ?
    C11 C12 C4 . . 124.1(3) ?
    N3 C13 N4 . . 111.7(3) ?
    N3 C13 C14 . . 125.1(3) ?
    N4 C13 C14 . . 123.2(3) ?
    C15 C14 C19 . . 118.0(3) ?
    C15 C14 C13 . . 120.7(3) ?
    C19 C14 C13 . . 121.2(4) ?
    C16 C15 C14 . . 121.6(4) ?
    C16 C15 H15 . . 119.2 ?
    C14 C15 H15 . . 119.2 ?
    C15 C16 C17 . . 119.7(4) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    O3 C17 C16 . . 123.1(4) ?
    O3 C17 C18 . . 117.4(4) ?
    C16 C17 C18 . . 119.5(4) ?
    C19 C18 C17 . . 120.2(4) ?
    C19 C18 H18 . . 119.9 ?
    C17 C18 H18 . . 119.9 ?
    C18 C19 C14 . . 120.9(4) ?
    C18 C19 H19 . . 119.6 ?
    C14 C19 H19 . . 119.6 ?
    O2 C20 O1 . . 124.9(3) ?
    O2 C20 C21 . . 118.4(3) ?
    O1 C20 C21 . . 116.6(3) ?
    C22 C21 C23 . 2_656 118.9(3) ?
    C22 C21 C20 . . 121.2(3) ?
    C23 C21 C20 2_656 . 119.8(3) ?
    C23 C22 C21 . . 120.5(4) ?
    C23 C22 H22 . . 119.8 ?
    C21 C22 H22 . . 119.8 ?
    C22 C23 C21 . 2_656 120.6(4) ?
    C22 C23 H23 . . 119.7 ?
    C21 C23 H23 2_656 . 119.7 ?
    C1 N1 C5 . . 118.7(3) ?
    C1 N1 Zn1 . . 128.5(3) ?
    C5 N1 Zn1 . . 112.8(2) ?
    C7 N2 C6 . . 118.7(3) ?
    C7 N2 Zn1 . . 125.7(3) ?
    C6 N2 Zn1 . . 115.5(2) ?
    C13 N3 C11 . . 105.1(3) ?
    C13 N4 C12 . . 107.8(3) ?
    C13 N4 H4 . . 126.1 ?
    C12 N4 H4 . . 126.1 ?
    C20 O1 Zn1 . . 125.1(2) ?
    Zn1 O1W HW11 . . 110(4) ?
    Zn1 O1W HW12 . . 96(3) ?
    HW11 O1W HW12 . . 106(5) ?
    C17 O3 H3A . . 109.5 ?
    HW21 O2W HW22 . . 101(3) ?
    O1 Zn1 N2 . . 90.17(11) y
    O1 Zn1 O1W . . 87.43(13) y
    N2 Zn1 O1W . . 124.01(13) y
    O1 Zn1 N1 . . 163.57(12) y
    N2 Zn1 N1 . . 78.13(12) y
    O1W Zn1 N1 . . 89.60(13) y
    O1 Zn1 Cl1 . . 98.97(10) y
    N2 Zn1 Cl1 . . 118.99(9) y
    O1W Zn1 Cl1 . . 116.62(11) y
    N1 Zn1 Cl1 . . 96.81(9) y
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
    O1W HW12 O2 . 0.87(5) 1.95(6) 2.774(5) 158(4)
    O1W HW11 O2 2_766 0.83(6) 1.88(6) 2.700(5) 172(6)
    O3 H3A O2W 2_575 0.82 1.90 2.713(5) 173
    N4 H4 Cl1 1_565 0.86 2.48 3.318(4) 165
    O2W HW21 N3 . 0.88(4) 2.01(2) 2.884(5) 172(6)
    O2W HW22 Cl1 2_665 0.941(19) 2.85(4) 3.571(4) 134(5)
