##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2012-07-02
_journal_date_accepted     2012-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     m1088
_journal_page_last     m1088
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536812031789
_journal_coeditor_code     XU5588
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Poly[[bis(μ-3-amino-5-carboxybenzoato-κ²N:O¹)diaquazinc]
dihydrate]
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhang, Kou-Lin'
;
College of Chemistry and Chemical Engineering
Yangzhou University
Yangzhou 225002
People's Republic of China
;
    'Qiu, Ting-Ting'
;
College of Chemistry and Chemical Engineering
Yangzhou University
Yangzhou 225002
People's Republic of China
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
     Chemistry Department
     King Abdulaziz University
     PO Box 80203 Jeddah
     Saudi Arabia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Poly[[bis(μ-3-amino-5-carboxybenzoato-
κ²N:O¹)diaquazinc] dihydrate]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N2 O10 Zn, 2H2 O'
_chemical_formula_sum     'C16 H20 N2 O12 Zn'
_chemical_formula_iupac     '[Zn (C8 H6 N O4)2 (H2 O)2], 2H2 O'
_chemical_formula_weight     497.71
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     14.2209(10)
_cell_length_b     11.2252(8)
_cell_length_c     12.7139(9)
_cell_angle_alpha     90.00
_cell_angle_beta     113.2860(10)
_cell_angle_gamma     90.00
_cell_volume     1864.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4815
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     28.15
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.773
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     1.392
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6802
_exptl_absorpt_correction_T_max     0.7878
_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 SMART APEX'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8005
_diffrn_reflns_av_R_equivalents     0.0177
_diffrn_reflns_av_sigmaI/netI     0.0163
_diffrn_reflns_theta_min     2.39
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2130
_reflns_number_gt     1843
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0385
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0949
_refine_ls_wR_factor_ref     0.0979
_refine_ls_goodness_of_fit_ref     1.070
_refine_ls_restrained_S_all     1.070
_refine_ls_number_reflns     2130
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0506P)²+3.2779P] 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     0.001
_refine_diff_density_max     0.373
_refine_diff_density_min     -0.371
_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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
               'OLEX (Dolomanov et al., 2003) and X-SEED (Barbour, 2001)'
_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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Zn Zn1 0.2500 0.2500 0.0000 0.02950(14) Uani d S 1 2 . .
    O O1 0.20751(15) 0.32463(16) 0.12770(14) 0.0412(4) Uani d . 1 1 . .
    O O2 0.1529(2) 0.1571(2) 0.1754(2) 0.0655(7) Uani d . 1 1 . .
    O O3 0.09628(17) 0.14472(16) 0.53610(16) 0.0436(4) Uani d . 1 1 . .
    H H1 0.0885 0.1154 0.5929 0.065 Uiso calc R 1 1 . .
    O O4 0.07472(15) 0.31377(16) 0.61500(15) 0.0408(4) Uani d . 1 1 . .
    O O1W 0.35790(16) 0.38916(19) 0.03707(18) 0.0531(5) Uani d . 1 1 . .
    H H2 0.3743 0.3994 -0.0189 0.080 Uiso calc R 1 1 . .
    H H3 0.4102 0.3714 0.0953 0.080 Uiso calc PR 0.50 1 . .
    H H3' 0.3322 0.4522 0.0496 0.080 Uiso calc PR 0.50 1 . .
    O O2W 0.0898(2) -0.04635(18) 0.22475(18) 0.0594(6) Uani d . 1 1 . .
    H H4 0.1052 0.0229 0.2118 0.089 Uiso d R 1 1 . .
    H H5 0.0334 -0.0439 0.2320 0.089 Uiso d PR 0.50 1 . .
    H H5' 0.1397 -0.0755 0.2797 0.089 Uiso d PR 0.50 1 . .
    N N1 0.12864(15) 0.64309(17) 0.36983(16) 0.0312(4) Uani d . 1 1 . .
    H H6 0.0705 0.6633 0.3742 0.037 Uiso calc R 1 1 . .
    H H7 0.1250 0.6675 0.3025 0.037 Uiso calc R 1 1 . .
    C C1 0.1718(2) 0.2655(2) 0.1878(2) 0.0349(5) Uani d . 1 1 . .
    C C2 0.15207(17) 0.3304(2) 0.28176(18) 0.0291(4) Uani d . 1 1 . .
    C C3 0.15228(17) 0.4538(2) 0.28397(18) 0.0294(5) Uani d . 1 1 . .
    H H3A 0.1667 0.4963 0.2293 0.035 Uiso calc R 1 1 . .
    C C4 0.13087(16) 0.5152(2) 0.36787(17) 0.0274(4) Uani d . 1 1 . .
    C C5 0.11166(17) 0.4506(2) 0.45058(18) 0.0295(5) Uani d . 1 1 . .
    H H5A 0.0982 0.4904 0.5073 0.035 Uiso calc R 1 1 . .
    C C6 0.11247(17) 0.3261(2) 0.44894(17) 0.0277(4) Uani d . 1 1 . .
    C C7 0.13167(19) 0.2662(2) 0.3638(2) 0.0302(5) Uani d . 1 1 . .
    H H7A 0.1309 0.1834 0.3618 0.036 Uiso calc R 1 1 . .
    C C8 0.09264(19) 0.2626(2) 0.54063(19) 0.0309(5) Uani d . 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Zn1 0.0412(2) 0.0297(2) 0.0248(2) -0.00028(15) 0.02079(16) -0.00161(13)
    O1 0.0631(12) 0.0436(10) 0.0312(9) 0.0127(9) 0.0339(8) 0.0038(7)
    O2 0.121(2) 0.0466(12) 0.0583(13) -0.0156(13) 0.0664(14) -0.0190(10)
    O3 0.0725(13) 0.0354(9) 0.0375(9) 0.0045(9) 0.0374(9) 0.0025(7)
    O4 0.0639(12) 0.0404(10) 0.0321(9) -0.0022(9) 0.0340(8) -0.0024(7)
    O1W 0.0501(11) 0.0531(12) 0.0538(12) -0.0046(9) 0.0181(9) -0.0207(10)
    O2W 0.1023(18) 0.0426(11) 0.0469(11) 0.0111(11) 0.0441(12) 0.0074(9)
    N1 0.0419(11) 0.0334(10) 0.0242(9) 0.0046(8) 0.0194(8) 0.0030(7)
    C1 0.0436(13) 0.0414(14) 0.0258(11) 0.0043(10) 0.0203(10) -0.0048(9)
    C2 0.0323(11) 0.0388(12) 0.0199(9) 0.0037(9) 0.0142(8) -0.0027(8)
    C3 0.0324(11) 0.0394(12) 0.0203(9) 0.0035(9) 0.0148(8) 0.0011(8)
    C4 0.0290(10) 0.0343(11) 0.0208(9) 0.0016(9) 0.0118(8) -0.0011(8)
    C5 0.0340(11) 0.0367(12) 0.0227(10) 0.0037(9) 0.0165(9) -0.0024(8)
    C6 0.0295(11) 0.0366(11) 0.0200(9) 0.0015(9) 0.0129(8) 0.0000(8)
    C7 0.0376(12) 0.0323(11) 0.0256(10) 0.0033(9) 0.0178(9) -0.0022(8)
    C8 0.0356(11) 0.0380(12) 0.0233(10) 0.0028(9) 0.0160(9) 0.0013(8)
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 O1W . 2.108(2) ?
    Zn1 O1W 7 2.108(2) ?
    Zn1 O1 . 2.1163(16) ?
    Zn1 O1 7 2.1163(16) ?
    Zn1 N1 6_565 2.214(2) ?
    Zn1 N1 4_545 2.214(2) ?
    O1 C1 . 1.261(3) ?
    O2 C1 . 1.243(3) ?
    O3 C8 . 1.326(3) ?
    O3 H1 . 0.8400 ?
    O4 C8 . 1.217(3) ?
    O1W H2 . 0.8400 ?
    O1W H3 . 0.8400 ?
    O1W H3' . 0.8400 ?
    O2W H4 . 0.8408 ?
    O2W H5 . 0.8425 ?
    O2W H5' . 0.8407 ?
    N1 C4 . 1.436(3) ?
    N1 Zn1 4 2.214(2) ?
    N1 H6 . 0.8800 ?
    N1 H7 . 0.8800 ?
    C1 C2 . 1.517(3) ?
    C2 C7 . 1.390(3) ?
    C2 C3 . 1.386(3) ?
    C3 C4 . 1.401(3) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.390(3) ?
    C5 C6 . 1.398(3) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.390(3) ?
    C6 C8 . 1.486(3) ?
    C7 H7A . 0.9300 ?
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
    O1W Zn1 O1W . 7 180.00(9) ?
    O1W Zn1 O1 . . 86.47(8) ?
    O1W Zn1 O1 7 . 93.53(8) ?
    O1W Zn1 O1 . 7 93.53(8) ?
    O1W Zn1 O1 7 7 86.47(8) ?
    O1 Zn1 O1 . 7 180.00(8) ?
    O1W Zn1 N1 . 6_565 92.80(8) ?
    O1W Zn1 N1 7 6_565 87.20(8) ?
    O1 Zn1 N1 . 6_565 89.10(7) ?
    O1 Zn1 N1 7 6_565 90.90(7) ?
    O1W Zn1 N1 . 4_545 87.20(8) ?
    O1W Zn1 N1 7 4_545 92.80(8) ?
    O1 Zn1 N1 . 4_545 90.90(7) ?
    O1 Zn1 N1 7 4_545 89.10(7) ?
    N1 Zn1 N1 6_565 4_545 180.00(18) ?
    C1 O1 Zn1 . . 124.19(16) ?
    C8 O3 H1 . . 109.5 ?
    Zn1 O1W H2 . . 109.5 ?
    Zn1 O1W H3 . . 109.5 ?
    H2 O1W H3 . . 109.5 ?
    Zn1 O1W H3' . . 109.5 ?
    H2 O1W H3' . . 109.5 ?
    H3 O1W H3' . . 109.5 ?
    H4 O2W H5 . . 108.9 ?
    H4 O2W H5' . . 108.8 ?
    H5 O2W H5' . . 116.7 ?
    C4 N1 Zn1 . 4 122.60(14) ?
    C4 N1 H6 . . 106.7 ?
    Zn1 N1 H6 4 . 106.7 ?
    C4 N1 H7 . . 106.7 ?
    Zn1 N1 H7 4 . 106.7 ?
    H6 N1 H7 . . 106.6 ?
    O2 C1 O1 . . 123.9(2) ?
    O2 C1 C2 . . 118.2(2) ?
    O1 C1 C2 . . 117.9(2) ?
    C7 C2 C3 . . 120.2(2) ?
    C7 C2 C1 . . 120.1(2) ?
    C3 C2 C1 . . 119.8(2) ?
    C2 C3 C4 . . 120.5(2) ?
    C2 C3 H3A . . 119.7 ?
    C4 C3 H3A . . 119.7 ?
    C5 C4 C3 . . 119.1(2) ?
    C5 C4 N1 . . 119.72(19) ?
    C3 C4 N1 . . 121.18(19) ?
    C4 C5 C6 . . 120.31(19) ?
    C4 C5 H5A . . 119.8 ?
    C6 C5 H5A . . 119.8 ?
    C7 C6 C5 . . 120.1(2) ?
    C7 C6 C8 . . 122.4(2) ?
    C5 C6 C8 . . 117.58(19) ?
    C2 C7 C6 . . 119.8(2) ?
    C2 C7 H7A . . 120.1 ?
    C6 C7 H7A . . 120.1 ?
    O4 C8 O3 . . 121.9(2) ?
    O4 C8 C6 . . 123.1(2) ?
    O3 C8 C6 . . 114.96(19) ?
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
    O1W Zn1 O1 C1 . . . . -150.9(2) ?
    O1W Zn1 O1 C1 7 . . . 29.1(2) ?
    N1 Zn1 O1 C1 6_565 . . . 116.2(2) ?
    N1 Zn1 O1 C1 4_545 . . . -63.8(2) ?
    Zn1 O1 C1 O2 . . . . -3.4(4) ?
    Zn1 O1 C1 C2 . . . . 175.68(15) ?
    O2 C1 C2 C7 . . . . 11.5(4) ?
    O1 C1 C2 C7 . . . . -167.7(2) ?
    O2 C1 C2 C3 . . . . -167.1(3) ?
    O1 C1 C2 C3 . . . . 13.8(3) ?
    C7 C2 C3 C4 . . . . -0.7(3) ?
    C1 C2 C3 C4 . . . . 177.9(2) ?
    C2 C3 C4 C5 . . . . 1.4(3) ?
    C2 C3 C4 N1 . . . . -178.7(2) ?
    Zn1 N1 C4 C5 4 . . . 72.4(2) ?
    Zn1 N1 C4 C3 4 . . . -107.5(2) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    N1 C4 C5 C6 . . . . 179.3(2) ?
    C4 C5 C6 C7 . . . . -0.6(3) ?
    C4 C5 C6 C8 . . . . 179.3(2) ?
    C3 C2 C7 C6 . . . . -0.7(3) ?
    C1 C2 C7 C6 . . . . -179.2(2) ?
    C5 C6 C7 C2 . . . . 1.3(3) ?
    C8 C6 C7 C2 . . . . -178.5(2) ?
    C7 C6 C8 O4 . . . . -179.2(2) ?
    C5 C6 C8 O4 . . . . 1.0(3) ?
    C7 C6 C8 O3 . . . . 1.0(3) ?
    C5 C6 C8 O3 . . . . -178.8(2) ?
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
    O3 H1 O2W 6_556 0.84 1.84 2.675(3) 172.3
    O1W H2 O2 7 0.84 1.97 2.695(3) 143.1
    O2W H4 O2 . 0.84 1.79 2.619(3) 169.9
    O2W H5 O2W 2 0.84 2.03 2.869(5) 170.9
    O2W H5' O1 4_545 0.84 2.31 3.106(3) 157.9
    O2W H5' O1W 4_545 0.84 2.35 2.910(3) 124.5
    N1 H6 O4 5_566 0.88 2.14 3.013(3) 171.9
    N1 H7 O4 6_565 0.88 2.21 3.059(2) 161.3
