##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-05-12
_journal_date_accepted     2008-05-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      7
_journal_page_first     o1225
_journal_page_last     o1225
_journal_paper_category     QO
_journal_coeditor_code     TK2271
_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
;
4-Hydroxy-1-oxo-1,2-dihydrophthalazine-6,7-dicarboxylic acid dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Liang, Ling-Ling'
;
     Department of Chemistry
     Shaanxi Key Laboratory for Physico-Inorganic Chemistry
     Northwest University
     Xi'an 710069
     People's Republic of China
;
    'Zhao, Jian-She'
;
     Department of Chemistry
     Shaanxi Key Laboratory for Physico-Inorganic Chemistry
     Northwest University
     Xi'an 710069
     People's Republic of China
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Hydroxy-1-oxo-1,2-dihydrophthalazine-6,7-dicarboxylic acid dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H6 N2 O6, 2(H2 O)'
_chemical_formula_sum     'C10 H10 N2 O8'
_chemical_formula_iupac     'C10 H6 N2 O6, 2H2 O'
_chemical_formula_weight     286.20
_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     6.40690(10)
_cell_length_b     9.4254(2)
_cell_length_c     9.6922(2)
_cell_angle_alpha     82.843(2)
_cell_angle_beta     87.4960(10)
_cell_angle_gamma     73.451(2)
_cell_volume     556.65(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2234
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.708
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.151
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(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
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4702
_diffrn_reflns_av_R_equivalents     0.017
_diffrn_reflns_av_sigmaI/netI     0.026
_diffrn_reflns_theta_min     2.1
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2530
_reflns_number_gt     2160
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.041
_refine_ls_R_factor_gt     0.035
_refine_ls_wR_factor_gt     0.100
_refine_ls_wR_factor_ref     0.105
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     2530
_refine_ls_number_parameters     221
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0657P)²+0.0694P] 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     0.43
_refine_diff_density_min     -0.24
_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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2008)'
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
    O O1 0.92046(15) 0.93958(11) 0.64792(10) 0.0166(2) Uani d D 1 . .
    O O2 0.86240(15) 0.86579(11) 0.87194(10) 0.0195(2) Uani d . 1 . .
    O O3 0.44292(15) 0.84970(10) 1.00234(9) 0.0155(2) Uani d D 1 . .
    O O4 0.68492(16) 0.62355(11) 1.02233(9) 0.0199(2) Uani d . 1 . .
    O O5 0.10736(15) 0.53241(11) 0.66473(9) 0.0180(2) Uani d D 1 . .
    O O6 0.49784(14) 0.82489(10) 0.27322(9) 0.0147(2) Uani d . 1 . .
    O O1W 1.14691(16) 1.06674(12) 0.78414(11) 0.0207(2) Uani d D 1 . .
    O O2W 0.85169(16) 0.35754(12) 0.90954(10) 0.0213(2) Uani d D 1 . .
    N N1 0.16571(17) 0.60686(12) 0.43675(11) 0.0136(2) Uani d . 1 . .
    N N2 0.27394(17) 0.68218(12) 0.34120(11) 0.0134(2) Uani d D 1 . .
    C C1 0.5698(2) 0.73086(14) 0.95287(13) 0.0129(3) Uani d . 1 . .
    C C2 0.54372(19) 0.73590(14) 0.79857(13) 0.0120(3) Uani d . 1 . .
    C C3 0.39766(19) 0.66628(14) 0.75724(13) 0.0126(3) Uani d D 1 . .
    C C4 0.35973(19) 0.67201(13) 0.61528(12) 0.0116(3) Uani d . 1 . .
    C C5 0.20578(19) 0.60273(14) 0.56725(13) 0.0126(3) Uani d . 1 . .
    C C6 0.41699(19) 0.75457(14) 0.36872(13) 0.0117(3) Uani d . 1 . .
    C C7 0.46733(19) 0.74720(14) 0.51629(12) 0.0114(3) Uani d . 1 . .
    C C8 0.61956(19) 0.81353(14) 0.55846(13) 0.0119(3) Uani d D 1 . .
    C C9 0.65794(19) 0.80760(14) 0.69923(12) 0.0117(3) Uani d . 1 . .
    C C10 0.8230(2) 0.87406(14) 0.74930(13) 0.0137(3) Uani d . 1 . .
    H H10 0.998(3) 0.980(2) 0.6878(19) 0.042(6) Uiso d D 1 . .
    H H30 0.458(3) 0.838(2) 1.0895(10) 0.036(5) Uiso d D 1 . .
    H H50 0.026(3) 0.496(2) 0.622(2) 0.048(6) Uiso d D 1 . .
    H H11 1.253(2) 1.101(2) 0.760(2) 0.044(6) Uiso d D 1 . .
    H H12 1.180(3) 1.0209(19) 0.8645(12) 0.034(5) Uiso d D 1 . .
    H H21 0.824(3) 0.4435(13) 0.9343(19) 0.034(5) Uiso d D 1 . .
    H H22 0.975(2) 0.314(3) 0.942(3) 0.074(8) Uiso d D 1 . .
    H H2 0.241(3) 0.681(2) 0.2530(11) 0.037(5) Uiso d D 1 . .
    H H3 0.320(2) 0.6187(16) 0.8236(13) 0.017(4) Uiso d D 1 . .
    H H8 0.693(2) 0.8618(17) 0.4898(14) 0.019(4) 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
    O1 C10 . 1.3235(15) ?
    O1 H10 . 0.840(10)
                     ?
    O2 C10 . 1.2143(16) ?
    O3 C1 . 1.3139(15) ?
    O3 H30 . 0.840(10)
                     ?
    O4 C1 . 1.2121(16) ?
    O5 C5 . 1.3265(15) ?
    O5 H50 . 0.850(10)
                     ?
    O6 C6 . 1.2511(15) ?
    O1W H11 . 0.850(10)
                      ?
    O1W H12 . 0.850(10)
                      ?
    O2W H21 . 0.840(10)
                      ?
    O2W H22 . 0.830(10)
                      ?
    N1 C5 . 1.2953(16) ?
    N1 N2 . 1.3794(14) ?
    N2 C6 . 1.3415(16) ?
    N2 H2 . 0.890(10)
                    ?
    C1 C2 . 1.5054(17) ?
    C2 C3 . 1.3838(17) ?
    C2 C9 . 1.4061(16) ?
    C3 C4 . 1.3993(17) ?
    C3 H3 . 0.941(9) ?
    C4 C7 . 1.3961(16) ?
    C4 C5 . 1.4487(16) ?
    C6 C7 . 1.4688(17) ?
    C7 C8 . 1.3983(17) ?
    C8 C9 . 1.3884(17) ?
    C8 H8 . 0.942(9) ?
    C9 C10 . 1.4981(17) ?
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
    C10 O1 H10 . . 105.3(14) ?
    C1 O3 H30 . . 107.8(13) ?
    C5 O5 H50 . . 106.0(15) ?
    H11 O1W H12 . . 104.8(18) ?
    H21 O2W H22 . . 104(2) ?
    C5 N1 N2 . . 117.77(10) ?
    C6 N2 N1 . . 126.82(10) ?
    C6 N2 H2 . . 119.3(12) ?
    N1 N2 H2 . . 113.9(12) ?
    O4 C1 O3 . . 125.08(12) ?
    O4 C1 C2 . . 122.51(12) ?
    O3 C1 C2 . . 112.24(10) ?
    C3 C2 C9 . . 120.51(11) ?
    C3 C2 C1 . . 116.41(11) ?
    C9 C2 C1 . . 123.07(11) ?
    C2 C3 C4 . . 119.19(11) ?
    C2 C3 H3 . . 120.6(9) ?
    C4 C3 H3 . . 120.2(10) ?
    C7 C4 C3 . . 120.56(11) ?
    C7 C4 C5 . . 118.31(11) ?
    C3 C4 C5 . . 121.13(11) ?
    N1 C5 O5 . . 120.97(11) ?
    N1 C5 C4 . . 122.70(11) ?
    O5 C5 C4 . . 116.32(11) ?
    O6 C6 N2 . . 121.07(11) ?
    O6 C6 C7 . . 123.23(11) ?
    N2 C6 C7 . . 115.70(11) ?
    C4 C7 C8 . . 119.99(11) ?
    C4 C7 C6 . . 118.67(11) ?
    C8 C7 C6 . . 121.35(11) ?
    C9 C8 C7 . . 119.53(11) ?
    C9 C8 H8 . . 121.9(10) ?
    C7 C8 H8 . . 118.6(10) ?
    C8 C9 C2 . . 120.16(11) ?
    C8 C9 C10 . . 121.46(11) ?
    C2 C9 C10 . . 118.37(11) ?
    O2 C10 O1 . . 124.29(11) ?
    O2 C10 C9 . . 122.03(11) ?
    O1 C10 C9 . . 113.68(11) ?
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
    C5 N1 N2 C6 . . . . -0.85(19) ?
    O4 C1 C2 C3 . . . . 81.31(15) ?
    O3 C1 C2 C3 . . . . -94.09(13) ?
    O4 C1 C2 C9 . . . . -99.19(15) ?
    O3 C1 C2 C9 . . . . 85.40(14) ?
    C9 C2 C3 C4 . . . . -1.98(19) ?
    C1 C2 C3 C4 . . . . 177.53(11) ?
    C2 C3 C4 C7 . . . . -0.12(19) ?
    C2 C3 C4 C5 . . . . -179.04(11) ?
    N2 N1 C5 O5 . . . . 179.93(10) ?
    N2 N1 C5 C4 . . . . -0.70(18) ?
    C7 C4 C5 N1 . . . . 0.56(19) ?
    C3 C4 C5 N1 . . . . 179.50(12) ?
    C7 C4 C5 O5 . . . . 179.95(11) ?
    C3 C4 C5 O5 . . . . -1.10(18) ?
    N1 N2 C6 O6 . . . . -176.72(11) ?
    N1 N2 C6 C7 . . . . 2.30(18) ?
    C3 C4 C7 C8 . . . . 2.03(19) ?
    C5 C4 C7 C8 . . . . -179.02(11) ?
    C3 C4 C7 C6 . . . . -177.98(11) ?
    C5 C4 C7 C6 . . . . 0.97(17) ?
    O6 C6 C7 C4 . . . . 176.75(11) ?
    N2 C6 C7 C4 . . . . -2.25(17) ?
    O6 C6 C7 C8 . . . . -3.27(19) ?
    N2 C6 C7 C8 . . . . 177.73(11) ?
    C4 C7 C8 C9 . . . . -1.82(19) ?
    C6 C7 C8 C9 . . . . 178.19(11) ?
    C7 C8 C9 C2 . . . . -0.26(19) ?
    C7 C8 C9 C10 . . . . 178.62(11) ?
    C3 C2 C9 C8 . . . . 2.19(19) ?
    C1 C2 C9 C8 . . . . -177.29(11) ?
    C3 C2 C9 C10 . . . . -176.73(11) ?
    C1 C2 C9 C10 . . . . 3.80(18) ?
    C8 C9 C10 O2 . . . . -177.84(12) ?
    C2 C9 C10 O2 . . . . 1.06(19) ?
    C8 C9 C10 O1 . . . . 1.46(17) ?
    C2 C9 C10 O1 . . . . -179.64(10) ?
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 . 0.840(10)
                         1.780(10)
                                 2.6150(10)
                                          175(2) y
    O3 H3o O6 1_556 0.840(10)
                            1.790(10)
                                    2.6370(10)
                                             176(2) y
    O5 H5o N1 2_566 0.850(10)
                            1.910(10)
                                    2.7440(10)
                                             168(2) y
    N2 H2 O2w 2_666 0.890(10)
                            1.820(10)
                                    2.6950(10)
                                             167(2) y
    O1w H11 O6 2_776 0.850(10)
                             1.910(10)
                                     2.7580(10)
                                              173(2) y
    O1w H12 O3 1_655 0.850(10)
                             2.310(10)
                                     3.0520(10)
                                              146(2) y
    O2w H21 O4 . 0.840(10)
                         1.960(10)
                                 2.7710(10)
                                          162(2) y
    O2w H22 O2 2_767 0.830(10)
                             2.37(2) 3.0500(10)
                                              139(2) y
