##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{(E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-
yliminomethyl)phenoxy]acetic acid monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H19 N3 O4, H2 O'
_chemical_formula_sum     'C20 H21 N3 O5'
_chemical_formula_iupac     'C20 H19 N3 O4, H2 O'
_chemical_formula_weight     383.40
_chemical_melting_point     '466.2-466.9'
_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     18.0213(15)
_cell_length_b     6.8755(6)
_cell_length_c     30.352(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.518(2)
_cell_angle_gamma     90.00
_cell_volume     3749.1(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1657
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.359
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1616
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.98
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(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 APEX-II area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10093
_diffrn_reflns_av_R_equivalents     0.0675
_diffrn_reflns_av_sigmaI/netI     0.0803
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.976
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -36
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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     3231
_reflns_number_gt     1522
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1236
_refine_ls_R_factor_gt     0.0516
_refine_ls_wR_factor_gt     0.1091
_refine_ls_wR_factor_ref     0.1265
_refine_ls_goodness_of_fit_ref     1.009
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     3231
_refine_ls_number_parameters     265
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0499P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.184
_refine_diff_density_min     -0.177
_refine_ls_extinction_method     APEX2
_refine_ls_extinction_coef     0.0009(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 2004)'
_computing_cell_refinement     'APEX2'
_computing_data_reduction     'APEX2'
_computing_structure_solution     'APEX2'
_computing_structure_refinement     'APEX2'
_computing_molecular_graphics     'APEX2'
_computing_publication_material     'APEX2'
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 -0.00791(11) 0.6046(3) 0.87063(7) 0.0610(6) Uani d . 1 . .
    O O2 0.18056(11) 0.8674(3) 0.94052(7) 0.0574(6) Uani d . 1 . .
    O O3 0.05648(12) 1.0462(4) 0.95971(8) 0.0841(8) Uani d . 1 . .
    O O4 0.12074(13) 1.2879(4) 0.99355(9) 0.0860(8) Uani d . 1 . .
    H H4A 0.0792 1.3259 0.9987 0.129 Uiso calc R 1 . .
    O O5 0.00245(16) 0.6615(5) 0.96328(10) 0.0902(8) Uani d D 1 . .
    N N1 -0.05004(12) 0.3334(3) 0.83101(8) 0.0489(7) Uani d . 1 . .
    N N2 -0.01738(13) 0.1641(4) 0.81545(8) 0.0492(6) Uani d . 1 . .
    N N3 0.14185(12) 0.3618(4) 0.87651(7) 0.0487(6) Uani d . 1 . .
    C C1 0.15482(16) 0.5224(5) 0.89700(9) 0.0497(8) Uani d . 1 . .
    H H1 0.1150 0.6028 0.9024 0.060 Uiso calc R 1 . .
    C C2 0.23058(15) 0.5836(4) 0.91218(9) 0.0449(8) Uani d . 1 . .
    C C3 0.24315(16) 0.7617(5) 0.93360(9) 0.0492(8) Uani d . 1 . .
    C C4 0.31477(17) 0.8228(5) 0.94696(10) 0.0574(9) Uani d . 1 . .
    H H4 0.3225 0.9411 0.9615 0.069 Uiso calc R 1 . .
    C C5 0.37456(18) 0.7064(6) 0.93853(11) 0.0668(10) Uani d . 1 . .
    H H5 0.4227 0.7480 0.9469 0.080 Uiso calc R 1 . .
    C C6 0.36338(17) 0.5296(5) 0.91789(10) 0.0672(10) Uani d . 1 . .
    H H6 0.4038 0.4507 0.9129 0.081 Uiso calc R 1 . .
    C C7 0.29245(16) 0.4699(5) 0.90473(10) 0.0591(9) Uani d . 1 . .
    H H7 0.2854 0.3508 0.8905 0.071 Uiso calc R 1 . .
    C C8 0.18960(16) 1.0448(4) 0.96428(9) 0.0531(8) Uani d . 1 . .
    H H8A 0.2168 1.1374 0.9476 0.064 Uiso calc R 1 . .
    H H8B 0.2176 1.0223 0.9924 0.064 Uiso calc R 1 . .
    C C9 0.11482(19) 1.1230(5) 0.97158(11) 0.0601(9) Uani d . 1 . .
    C C10 0.00416(16) 0.4392(5) 0.85674(9) 0.0479(8) Uani d . 1 . .
    C C11 0.06979(16) 0.3183(4) 0.85914(9) 0.0437(8) Uani d . 1 . .
    C C12 0.05254(16) 0.1511(4) 0.83597(9) 0.0465(8) Uani d . 1 . .
    C C13 0.09902(16) -0.0241(4) 0.83191(10) 0.0640(9) Uani d . 1 . .
    H H13A 0.1462 -0.0057 0.8484 0.096 Uiso calc R 1 . .
    H H13B 0.1068 -0.0456 0.8014 0.096 Uiso calc R 1 . .
    H H13C 0.0743 -0.1347 0.8433 0.096 Uiso calc R 1 . .
    C C14 -0.06675(17) -0.0012(4) 0.80614(10) 0.0636(9) Uani d . 1 . .
    H H14A -0.0792 -0.0584 0.8334 0.095 Uiso calc R 1 . .
    H H14B -0.0422 -0.0960 0.7892 0.095 Uiso calc R 1 . .
    H H14C -0.1114 0.0420 0.7897 0.095 Uiso calc R 1 . .
    C C15 -0.10746(15) 0.4290(4) 0.80384(9) 0.0440(8) Uani d . 1 . .
    C C16 -0.10647(15) 0.4333(4) 0.75853(10) 0.0492(8) Uani d . 1 . .
    H H16 -0.0699 0.3658 0.7448 0.059 Uiso calc R 1 . .
    C C17 -0.16005(16) 0.5383(5) 0.73342(10) 0.0560(9) Uani d . 1 . .
    H H17 -0.1601 0.5393 0.7028 0.067 Uiso calc R 1 . .
    C C18 -0.21312(16) 0.6412(4) 0.75379(11) 0.0562(9) Uani d . 1 . .
    H H18 -0.2483 0.7148 0.7370 0.067 Uiso calc R 1 . .
    C C19 -0.21403(16) 0.6349(4) 0.79913(11) 0.0581(9) Uani d . 1 . .
    H H19 -0.2502 0.7037 0.8129 0.070 Uiso calc R 1 . .
    C C20 -0.16193(16) 0.5276(4) 0.82428(10) 0.0551(9) Uani d . 1 . .
    H H20 -0.1634 0.5217 0.8548 0.066 Uiso calc R 1 . .
    H H5A 0.023(2) 0.779(3) 0.9636(12) 0.106(17) Uiso d D 1 . .
    H H5B -0.004(3) 0.624(7) 0.9351(9) 0.25(4) 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
    O1 C10 . 1.238(3) y
    O2 C3 . 1.372(3) ?
    O2 C8 . 1.420(3) ?
    O3 C9 . 1.206(4) ?
    O4 C9 . 1.315(4) ?
    O4 H4A . 0.8200 ?
    O5 H5A . 0.883(18) ?
    O5 H5B . 0.892(19) ?
    N1 N2 . 1.403(3) y
    N1 C10 . 1.405(3) y
    N1 C15 . 1.432(3) y
    N2 C12 . 1.364(3) y
    N2 C14 . 1.457(3) y
    N3 C1 . 1.280(3) y
    N3 C11 . 1.395(3) y
    C1 C2 . 1.468(4) y
    C1 H1 . 0.9300 ?
    C2 C7 . 1.395(4) ?
    C2 C3 . 1.396(4) ?
    C3 C4 . 1.387(4) ?
    C4 C5 . 1.382(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.375(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.372(4) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.484(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C10 C11 . 1.443(4) ?
    C11 C12 . 1.370(4) y
    C12 C13 . 1.478(4) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 C16 . 1.377(4) ?
    C15 C20 . 1.380(4) ?
    C16 C17 . 1.385(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.375(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.378(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.377(4) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 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
    C3 O2 C8 . . 118.0(2) ?
    C9 O4 H4A . . 109.5 ?
    H5A O5 H5B . . 108(3) ?
    N2 N1 C10 . . 109.0(2) y
    N2 N1 C15 . . 119.4(2) y
    C10 N1 C15 . . 121.4(2) y
    C12 N2 N1 . . 107.3(2) y
    C12 N2 C14 . . 124.5(3) y
    N1 N2 C14 . . 116.5(2) y
    C1 N3 C11 . . 119.9(3) y
    N3 C1 C2 . . 122.0(3) y
    N3 C1 H1 . . 119.0 ?
    C2 C1 H1 . . 119.0 ?
    C7 C2 C3 . . 117.7(3) ?
    C7 C2 C1 . . 121.6(3) ?
    C3 C2 C1 . . 120.7(3) ?
    O2 C3 C4 . . 123.5(3) ?
    O2 C3 C2 . . 115.5(3) ?
    C4 C3 C2 . . 121.0(3) ?
    C5 C4 C3 . . 119.4(3) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C6 C5 C4 . . 120.5(3) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C7 C6 C5 . . 119.8(3) ?
    C7 C6 H6 . . 120.1 ?
    C5 C6 H6 . . 120.1 ?
    C6 C7 C2 . . 121.6(3) ?
    C6 C7 H7 . . 119.2 ?
    C2 C7 H7 . . 119.2 ?
    O2 C8 C9 . . 108.6(3) ?
    O2 C8 H8A . . 110.0 ?
    C9 C8 H8A . . 110.0 ?
    O2 C8 H8B . . 110.0 ?
    C9 C8 H8B . . 110.0 ?
    H8A C8 H8B . . 108.4 ?
    O3 C9 O4 . . 124.3(3) ?
    O3 C9 C8 . . 125.2(3) ?
    O4 C9 C8 . . 110.5(3) ?
    O1 C10 N1 . . 122.1(3) y
    O1 C10 C11 . . 132.6(3) y
    N1 C10 C11 . . 105.1(3) ?
    C12 C11 N3 . . 122.7(3) ?
    C12 C11 C10 . . 107.8(3) ?
    N3 C11 C10 . . 129.1(3) ?
    N2 C12 C11 . . 110.1(3) ?
    N2 C12 C13 . . 121.6(3) ?
    C11 C12 C13 . . 128.3(3) ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N2 C14 H14A . . 109.5 ?
    N2 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    N2 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C16 C15 C20 . . 120.3(3) ?
    C16 C15 N1 . . 121.3(3) ?
    C20 C15 N1 . . 118.3(3) ?
    C15 C16 C17 . . 119.8(3) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C18 C17 C16 . . 120.0(3) ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C17 C18 C19 . . 119.8(3) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C20 C19 C18 . . 120.6(3) ?
    C20 C19 H19 . . 119.7 ?
    C18 C19 H19 . . 119.7 ?
    C19 C20 C15 . . 119.5(3) ?
    C19 C20 H20 . . 120.3 ?
    C15 C20 H20 . . 120.3 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O4 H4A O5 . . 5_577 0.82 1.94 2.688(4) 151.0 yes
    O5 H5B O1 . . ? 0.89(2) 1.96(3) 2.831(4) 166(4) yes
    O5 H5A O3 . . ? 0.88(2) 1.95(3) 2.823(4) 173(4) yes
    C4 H4 O4 . . 7_577 0.93 2.48 3.383(4) 163.0 yes
    C13 H13C O1 . . 1_545 0.96 2.51 3.459(4) 171.5 yes
data_global
_journal_date_recd_electronic     2006-07-03
_journal_date_accepted     2006-07-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      8
_journal_page_first     o3558
_journal_page_last     o3560
_journal_paper_category     EO
_journal_coeditor_code     HG2063
_publ_contact_author_name     'Xiao-Niu Fang'
_publ_contact_author_address
;
      College of Chemistry & Chemical Engineering
      JingGangShan University
      343009 Ji'an, JiangXi
      China
;
_publ_contact_author_email     fangxiaoniu@163.com
_publ_contact_author_fax     '+86-796-8100490'
_publ_contact_author_phone     '+86-796-8859572'
_publ_section_title
;
{(E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-
yliminomethyl)phenoxy]acetic acid monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Hu, Rong-Hua'
;
JiangXi Province Key Laboratory of Coordination Chemistry
 College of Chemistry and Chemical Engineering
 JingGangShan University
 343009 Ji'an, JiangXi
 People's Republic of China
;
    'Fang, Xiao-Niu'
;
JiangXi Province Key Laboratory of Coordination Chemistry
 College of Chemistry and Chemical Engineering
 JingGangShan University
 343009 Ji'an, JiangXi
 People's Republic of China
;
    'Sui, Yan'
;
JiangXi Province Key Laboratory of Coordination Chemistry
 College of Chemistry and Chemical Engineering
 JingGangShan University
 343009 Ji'an, JiangXi
 People's Republic of China
;
    'Luo, Qiu-Yan'
;
JiangXi Province Key Laboratory of Coordination Chemistry
 College of Chemistry and Chemical Engineering
 JingGangShan University
 343009 Ji'an, JiangXi
 People's Republic of China
;
    'Zou, Meng-Qiang'
;
JiangXi Province Key Laboratory of Coordination Chemistry
 College of Chemistry and Chemical Engineering
 JingGangShan University
 343009 Ji'an, JiangXi
 People's Republic of China
;
