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###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 4-(3-chlorophenyl)-3,6-dihydroxy-6-methyl-2-(2-pyridyl)-4,5,6,7-
tetrahydroindazole-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H22 Cl N3 O4'
_chemical_formula_sum     'C22 H22 Cl N3 O4'
_chemical_formula_iupac     'C22 H22 Cl N3 O4'
_chemical_formula_weight     427.88
_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     8.585(5)
_cell_length_b     9.053(3)
_cell_length_c     14.884(3)
_cell_angle_alpha     94.68(2)
_cell_angle_beta     90.19(2)
_cell_angle_gamma     115.66(3)
_cell_volume     1038.3(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1965
_cell_measurement_theta_min     2.51
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.218
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.9374
_exptl_absorpt_correction_T_max     0.9576
_exptl_special_details
;
;
_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 Kappa APEXII CCD diffractometer'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4446
_diffrn_reflns_av_R_equivalents     0.0097
_diffrn_reflns_av_sigmaI/netI     0.0128
_diffrn_reflns_theta_min     2.51
_diffrn_reflns_theta_max     24.97
_diffrn_reflns_theta_full     24.97
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_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 >
σ(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     3647
_reflns_number_gt     3025
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0425
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_gt     0.0865
_refine_ls_wR_factor_ref     0.0923
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     3647
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0426P)²+0.3338P] 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     0.242
_refine_diff_density_min     -0.301
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0065(15)
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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 (Bruker, 2004)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 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
    C C1 0.23589(18) 0.01801(18) 0.72716(10) 0.0366(3) Uani d . 1 . .
    H H1 0.2978 -0.0511 0.7220 0.044 Uiso calc R 1 . .
    C C2 0.07219(19) -0.06547(18) 0.66275(10) 0.0375(3) Uani d . 1 . .
    C C3 0.12780(19) -0.09587(18) 0.56754(10) 0.0396(4) Uani d . 1 . .
    H H3A 0.1634 -0.1841 0.5665 0.048 Uiso calc R 1 . .
    H H3B 0.0304 -0.1297 0.5248 0.048 Uiso calc R 1 . .
    C C4 0.27363(19) 0.05594(18) 0.54012(10) 0.0361(3) Uani d . 1 . .
    C C5 0.38310(19) 0.18470(18) 0.60252(10) 0.0369(3) Uani d . 1 . .
    C C6 0.36178(19) 0.19180(18) 0.70250(10) 0.0356(3) Uani d . 1 . .
    H H6 0.3088 0.2666 0.7180 0.043 Uiso calc R 1 . .
    C C7 0.53145(18) 0.25391(18) 0.75799(10) 0.0351(3) Uani d . 1 . .
    C C8 0.5566(2) 0.3545(2) 0.83731(10) 0.0414(4) Uani d . 1 . .
    H H8 0.4731 0.3891 0.8551 0.050 Uiso calc R 1 . .
    C C9 0.7067(2) 0.4029(2) 0.88964(10) 0.0447(4) Uani d . 1 . .
    C C10 0.8331(2) 0.3542(2) 0.86565(11) 0.0469(4) Uani d . 1 . .
    H H10 0.9332 0.3878 0.9019 0.056 Uiso calc R 1 . .
    C C11 0.8082(2) 0.2543(2) 0.78656(11) 0.0469(4) Uani d . 1 . .
    H H11 0.8920 0.2196 0.7693 0.056 Uiso calc R 1 . .
    C C12 0.6592(2) 0.2054(2) 0.73290(11) 0.0417(4) Uani d . 1 . .
    H H12 0.6445 0.1393 0.6794 0.050 Uiso calc R 1 . .
    C C13 0.1873(2) 0.0274(2) 0.82426(11) 0.0427(4) Uani d . 1 . .
    C C14 0.1681(4) -0.0911(3) 0.96324(14) 0.0803(7) Uani d . 1 . .
    H H14A 0.1570 -0.1955 0.9816 0.096 Uiso calc R 1 . .
    H H14B 0.0556 -0.0903 0.9672 0.096 Uiso calc R 1 . .
    C C15 0.2938(3) 0.0447(3) 1.02645(15) 0.0851(7) Uani d . 1 . .
    H H15A 0.4060 0.0462 1.0219 0.128 Uiso calc R 1 . .
    H H15B 0.2568 0.0276 1.0871 0.128 Uiso calc R 1 . .
    H H15C 0.2997 0.1479 1.0111 0.128 Uiso calc R 1 . .
    C C16 -0.0561(2) -0.2271(2) 0.69547(12) 0.0507(4) Uani d . 1 . .
    H H16A -0.0970 -0.2058 0.7528 0.076 Uiso calc R 1 . .
    H H16B -0.0002 -0.2976 0.7018 0.076 Uiso calc R 1 . .
    H H16C -0.1521 -0.2799 0.6525 0.076 Uiso calc R 1 . .
    C C17 0.5006(2) 0.29568(19) 0.55071(10) 0.0413(4) Uani d . 1 . .
    C C18 0.5488(2) 0.30146(19) 0.38582(11) 0.0402(4) Uani d . 1 . .
    C C19 0.4867(2) 0.2333(2) 0.29936(11) 0.0466(4) Uani d . 1 . .
    H H19 0.3820 0.1401 0.2887 0.056 Uiso calc R 1 . .
    C C20 0.5862(3) 0.3088(2) 0.22937(12) 0.0575(5) Uani d . 1 . .
    H H20 0.5490 0.2663 0.1701 0.069 Uiso calc R 1 . .
    C C21 0.7400(3) 0.4464(3) 0.24685(13) 0.0605(5) Uani d . 1 . .
    H H21 0.8084 0.4975 0.2000 0.073 Uiso calc R 1 . .
    C C22 0.7904(2) 0.5064(2) 0.33443(13) 0.0584(5) Uani d . 1 . .
    H H22 0.8939 0.6006 0.3462 0.070 Uiso calc R 1 . .
    N N1 0.31575(16) 0.08157(15) 0.45512(8) 0.0394(3) Uani d . 1 . .
    N N2 0.45910(16) 0.23300(15) 0.46190(8) 0.0408(3) Uani d . 1 . .
    N N3 0.69768(19) 0.43596(18) 0.40430(10) 0.0510(4) Uani d . 1 . .
    O O1 0.12768(17) 0.11693(18) 0.85661(8) 0.0608(4) Uani d . 1 . .
    O O2 0.21903(18) -0.07785(16) 0.87015(8) 0.0602(3) Uani d . 1 . .
    O O3 -0.00213(13) 0.04846(13) 0.66127(7) 0.0443(3) Uani d . 1 . .
    H H3 -0.0884 0.0092 0.6272 0.066 Uiso calc R 1 . .
    O O4 0.63299(16) 0.44010(14) 0.57502(8) 0.0589(3) Uani d . 1 . .
    H H4 0.6822 0.4810 0.5300 0.088 Uiso calc R 1 . .
    Cl Cl1 0.73648(7) 0.52862(8) 0.98989(3) 0.0772(2) Uani 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
    C1 C13 . 1.512(2) ?
    C1 C6 . 1.550(2) ?
    C1 C2 . 1.555(2) ?
    C1 H1 . 0.9800 ?
    C2 O3 . 1.4300(19) ?
    C2 C16 . 1.521(2) ?
    C2 C3 . 1.538(2) ?
    C3 C4 . 1.492(2) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 N1 . 1.328(2) ?
    C4 C5 . 1.405(2) ?
    C5 C17 . 1.369(2) ?
    C5 C6 . 1.500(2) ?
    C6 C7 . 1.525(2) ?
    C6 H6 . 0.9800 ?
    C7 C8 . 1.387(2) ?
    C7 C12 . 1.389(2) ?
    C8 C9 . 1.381(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.375(2) ?
    C9 Cl1 . 1.7482(17) ?
    C10 C11 . 1.381(2) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.384(2) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 O1 . 1.204(2) ?
    C13 O2 . 1.333(2) ?
    C14 O2 . 1.453(2) ?
    C14 C15 . 1.489(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 O4 . 1.3287(19) ?
    C17 N2 . 1.377(2) ?
    C18 N3 . 1.337(2) ?
    C18 C19 . 1.379(2) ?
    C18 N2 . 1.402(2) ?
    C19 C20 . 1.378(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.372(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.363(3) ?
    C21 H21 . 0.9300 ?
    C22 N3 . 1.340(2) ?
    C22 H22 . 0.9300 ?
    N1 N2 . 1.3854(19) ?
    O3 H3 . 0.8200 ?
    O4 H4 . 0.8200 ?
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
    C13 C1 C6 . . 109.76(12) ?
    C13 C1 C2 . . 111.12(12) ?
    C6 C1 C2 . . 113.02(12) ?
    C13 C1 H1 . . 107.6 ?
    C6 C1 H1 . . 107.6 ?
    C2 C1 H1 . . 107.6 ?
    O3 C2 C16 . . 110.78(13) ?
    O3 C2 C3 . . 109.40(13) ?
    C16 C2 C3 . . 110.15(13) ?
    O3 C2 C1 . . 106.58(12) ?
    C16 C2 C1 . . 111.06(13) ?
    C3 C2 C1 . . 108.78(12) ?
    C4 C3 C2 . . 110.91(12) ?
    C4 C3 H3A . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    C4 C3 H3B . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.0 ?
    N1 C4 C5 . . 113.24(14) ?
    N1 C4 C3 . . 123.79(13) ?
    C5 C4 C3 . . 122.95(14) ?
    C17 C5 C4 . . 104.49(13) ?
    C17 C5 C6 . . 130.71(13) ?
    C4 C5 C6 . . 124.75(14) ?
    C5 C6 C7 . . 113.80(13) ?
    C5 C6 C1 . . 108.64(12) ?
    C7 C6 C1 . . 110.03(12) ?
    C5 C6 H6 . . 108.1 ?
    C7 C6 H6 . . 108.1 ?
    C1 C6 H6 . . 108.1 ?
    C8 C7 C12 . . 118.85(14) ?
    C8 C7 C6 . . 119.86(13) ?
    C12 C7 C6 . . 121.22(13) ?
    C9 C8 C7 . . 119.45(15) ?
    C9 C8 H8 . . 120.3 ?
    C7 C8 H8 . . 120.3 ?
    C10 C9 C8 . . 122.03(15) ?
    C10 C9 Cl1 . . 118.91(12) ?
    C8 C9 Cl1 . . 119.06(13) ?
    C9 C10 C11 . . 118.52(15) ?
    C9 C10 H10 . . 120.7 ?
    C11 C10 H10 . . 120.7 ?
    C10 C11 C12 . . 120.31(15) ?
    C10 C11 H11 . . 119.8 ?
    C12 C11 H11 . . 119.8 ?
    C11 C12 C7 . . 120.83(15) ?
    C11 C12 H12 . . 119.6 ?
    C7 C12 H12 . . 119.6 ?
    O1 C13 O2 . . 123.97(16) ?
    O1 C13 C1 . . 125.16(15) ?
    O2 C13 C1 . . 110.87(14) ?
    O2 C14 C15 . . 112.8(2) ?
    O2 C14 H14A . . 109.0 ?
    C15 C14 H14A . . 109.0 ?
    O2 C14 H14B . . 109.0 ?
    C15 C14 H14B . . 109.0 ?
    H14A C14 H14B . . 107.8 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C2 C16 H16A . . 109.5 ?
    C2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O4 C17 C5 . . 130.01(14) ?
    O4 C17 N2 . . 122.42(15) ?
    C5 C17 N2 . . 107.56(13) ?
    N3 C18 C19 . . 123.45(16) ?
    N3 C18 N2 . . 114.62(14) ?
    C19 C18 N2 . . 121.93(15) ?
    C20 C19 C18 . . 117.28(17) ?
    C20 C19 H19 . . 121.4 ?
    C18 C19 H19 . . 121.4 ?
    C21 C20 C19 . . 120.22(18) ?
    C21 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
    C22 C21 C20 . . 118.54(18) ?
    C22 C21 H21 . . 120.7 ?
    C20 C21 H21 . . 120.7 ?
    N3 C22 C21 . . 122.97(18) ?
    N3 C22 H22 . . 118.5 ?
    C21 C22 H22 . . 118.5 ?
    C4 N1 N2 . . 103.89(12) ?
    C17 N2 N1 . . 110.81(13) ?
    C17 N2 C18 . . 127.39(13) ?
    N1 N2 C18 . . 121.72(13) ?
    C18 N3 C22 . . 117.54(16) ?
    C13 O2 C14 . . 117.31(16) ?
    C2 O3 H3 . . 109.5 ?
    C17 O4 H4 . . 109.5 ?
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
    C13 C1 C2 O3 . . . . 70.80(16) ?
    C6 C1 C2 O3 . . . . -53.11(16) ?
    C13 C1 C2 C16 . . . . -49.95(17) ?
    C6 C1 C2 C16 . . . . -173.86(13) ?
    C13 C1 C2 C3 . . . . -171.33(13) ?
    C6 C1 C2 C3 . . . . 64.75(16) ?
    O3 C2 C3 C4 . . . . 66.92(16) ?
    C16 C2 C3 C4 . . . . -171.08(13) ?
    C1 C2 C3 C4 . . . . -49.14(17) ?
    C2 C3 C4 N1 . . . . -160.33(14) ?
    C2 C3 C4 C5 . . . . 21.3(2) ?
    N1 C4 C5 C17 . . . . -0.35(18) ?
    C3 C4 C5 C17 . . . . 178.15(14) ?
    N1 C4 C5 C6 . . . . 177.45(14) ?
    C3 C4 C5 C6 . . . . -4.0(2) ?
    C17 C5 C6 C7 . . . . -44.3(2) ?
    C4 C5 C6 C7 . . . . 138.48(15) ?
    C17 C5 C6 C1 . . . . -167.28(16) ?
    C4 C5 C6 C1 . . . . 15.5(2) ?
    C13 C1 C6 C5 . . . . -170.09(12) ?
    C2 C1 C6 C5 . . . . -45.43(16) ?
    C13 C1 C6 C7 . . . . 64.71(16) ?
    C2 C1 C6 C7 . . . . -170.63(12) ?
    C5 C6 C7 C8 . . . . 142.41(15) ?
    C1 C6 C7 C8 . . . . -95.41(17) ?
    C5 C6 C7 C12 . . . . -40.7(2) ?
    C1 C6 C7 C12 . . . . 81.54(17) ?
    C12 C7 C8 C9 . . . . -0.5(2) ?
    C6 C7 C8 C9 . . . . 176.50(15) ?
    C7 C8 C9 C10 . . . . -0.1(3) ?
    C7 C8 C9 Cl1 . . . . -179.58(12) ?
    C8 C9 C10 C11 . . . . 0.2(3) ?
    Cl1 C9 C10 C11 . . . . 179.72(13) ?
    C9 C10 C11 C12 . . . . 0.3(3) ?
    C10 C11 C12 C7 . . . . -0.9(3) ?
    C8 C7 C12 C11 . . . . 1.0(2) ?
    C6 C7 C12 C11 . . . . -176.00(15) ?
    C6 C1 C13 O1 . . . . 54.3(2) ?
    C2 C1 C13 O1 . . . . -71.5(2) ?
    C6 C1 C13 O2 . . . . -125.83(14) ?
    C2 C1 C13 O2 . . . . 108.41(15) ?
    C4 C5 C17 O4 . . . . 179.84(17) ?
    C6 C5 C17 O4 . . . . 2.2(3) ?
    C4 C5 C17 N2 . . . . 0.32(17) ?
    C6 C5 C17 N2 . . . . -177.30(15) ?
    N3 C18 C19 C20 . . . . 0.6(3) ?
    N2 C18 C19 C20 . . . . -179.03(15) ?
    C18 C19 C20 C21 . . . . -0.2(3) ?
    C19 C20 C21 C22 . . . . -0.5(3) ?
    C20 C21 C22 N3 . . . . 0.9(3) ?
    C5 C4 N1 N2 . . . . 0.23(17) ?
    C3 C4 N1 N2 . . . . -178.26(13) ?
    O4 C17 N2 N1 . . . . -179.77(14) ?
    C5 C17 N2 N1 . . . . -0.21(18) ?
    O4 C17 N2 C18 . . . . 3.5(3) ?
    C5 C17 N2 C18 . . . . -176.92(14) ?
    C4 N1 N2 C17 . . . . -0.01(16) ?
    C4 N1 N2 C18 . . . . 176.92(13) ?
    N3 C18 N2 C17 . . . . 5.5(2) ?
    C19 C18 N2 C17 . . . . -174.84(15) ?
    N3 C18 N2 N1 . . . . -170.91(13) ?
    C19 C18 N2 N1 . . . . 8.8(2) ?
    C19 C18 N3 C22 . . . . -0.3(3) ?
    N2 C18 N3 C22 . . . . 179.38(15) ?
    C21 C22 N3 C18 . . . . -0.5(3) ?
    O1 C13 O2 C14 . . . . 3.9(3) ?
    C1 C13 O2 C14 . . . . -175.97(16) ?
    C15 C14 O2 C13 . . . . -79.9(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
    O4 H4 N3 . 0.82 1.90 2.604(3) 143.4
    O3 H3 N1 2_556 0.82 2.10 2.920(2) 176
    C11 H11 O3 1_655 0.93 2.58 3.418(3) 150.7
    C16 H16C O4 1_445 0.96 2.57 3.397(3) 144
data_global
_journal_date_recd_electronic     2010-03-10
_journal_date_accepted     2010-03-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o861
_journal_page_last     o861
_journal_paper_category     QO
_journal_coeditor_code     NG2744
_publ_contact_author_name     'Yeon Tae Jeong'
_publ_contact_author_address
;
      Division of Image and Information Engineering
      Pukyong National University
      Busan 608-739
      Republic of Korea
;
_publ_contact_author_email     ytjeong@pknu.ac.kr
_publ_contact_author_fax     '+82-51-629-6408'
_publ_contact_author_phone     '+82-51-629-6411'
_publ_section_title
;\
Ethyl
4-(3-chlorophenyl)-3,6-dihydroxy-6-methyl-2-(2-pyridyl)-4,5,6,7-\
tetrahydroindazole-5-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'S. Amirthaganesan'
;     Division of Image Science and Information Engineering
      Pukyong National University
      Busan 608-739
      Republic of Korea
;
    'G. Aridoss'
;     Division of Image Science and Information Engineering
      Pukyong National University
      Busan 608-739
      Republic of Korea
;
    'D.Gayathri'
;     Institute of Structural Biology and Biophysics-2: Molecular Biophysics
      Research Centre Jülich
      D-52425 Jülich
      Germany
;
    'Keun Soo Park'
;     Division of Image Science and Information Engineering
      Pukyong National University
      Busan 608-739
      Republic of Korea
;
    'Yeon Tae Jeong'
;     Division of Image Science and Information Engineering
      Pukyong National University
      Busan 608-739
      Republic of Korea
;
