##############################################################################
###                                                                        ###
###        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.                                        #
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# 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     SHELXL-97
_journal_date_recd_electronic     2006-03-22
_journal_date_accepted     2006-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o3776
_journal_page_last     o3777
_journal_paper_category     EO
_journal_coeditor_code     GH2004
_publ_contact_author_name     'Dr. Ziwei Huang'
_publ_contact_author_address
; The Burnham Institute for Medical Research
  10901 N. Torrey Pines Rd.
  La Jolla, CA 92037
  USA
;
_publ_contact_author_email     ziweihuang@burnham.org
_publ_contact_author_fax     '001 858 713 9927'
_publ_contact_author_phone     '001 858 646 3100 ext. 3928'
_publ_section_title
;
[3-(2-Hydroxyphenyl)-5-phenyl-4,5-dihydropyrazol-1-yl](pyridin-3-yl)methanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Nie, Aihua' .
; The Burnham Institute for Medical Research
  10901 N. Torrey Pines Rd.
  La Jolla, CA 92037
  USA
;
    'Ghosh, Sutapa' .
; The Burnham Institute for Medical Research
  10901 N. Torrey Pines Rd.
  La Jolla, CA 92037
  USA
;
    'Huang, Ziwei' .
; The Burnham Institute for Medical Research
  10901 N. Torrey Pines Rd.
  La Jolla, CA 92037
  USA
;
data_I
_chemical_name_systematic
;
[3-(2-Hydroxyphenyl)-5-phenyl-4,5-dihydropyrazol-1-yl](pyridin-3-yl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H17 N3 O2'
_chemical_formula_sum     'C21 H17 N3 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C21 H17 N3 O2'
_chemical_formula_weight     343.38
_chemical_melting_point     168
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.9050(10)
_cell_length_b     19.840(3)
_cell_length_c     14.283(2)
_cell_angle_alpha     90.00
_cell_angle_beta     97.516(3)
_cell_angle_gamma     90.00
_cell_volume     1659.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3690
_cell_measurement_theta_min     2.51
_cell_measurement_theta_max     26.57
_cell_measurement_temperature     100(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.375
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9821
_exptl_absorpt_correction_T_max     0.9821
_exptl_special_details
;
¹H NMR (300 MHz, DMSO-d₆): δ 10.070
(s, 1H), 9.009 (s, 1H,), 8.732 (d, 1H, J = 4.8
Hz), 8.233 (d, 1H, J = 6.9 Hz), 7.583--7.538 (m, 2H),
7.397--7.317 (m, 6H), 6.956--6.895 (m, 2H), 5.755 (dd,
1H, J₁ = 11.7 Hz, J₂ = 4.8Hz), 4.065 (d, 1H,
J₁ = 18.3 Hz, J₂ = 11.7 Hz), 3.318 (d, 1H, J
= 5.7 Hz).
;
_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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     13968
_diffrn_reflns_av_R_equivalents     0.0485
_diffrn_reflns_av_sigmaI/netI     0.0552
_diffrn_reflns_theta_min     1.77
_diffrn_reflns_theta_max     27.53
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     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     3742
_reflns_number_gt     2687
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0720
_refine_ls_R_factor_gt     0.0441
_refine_ls_wR_factor_gt     0.0975
_refine_ls_wR_factor_ref     0.1070
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3742
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0496P)²+0.1984P] 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     0.239
_refine_diff_density_min     -0.242
_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     'SMART (Bruker, 2005)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SI2004 (Altomare et al.,  1993)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-32 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 -0.1694(3) 0.08235(8) 0.32846(11) 0.0224(4) Uani d . 1 . .
    H H1A -0.2693 0.0493 0.2976 0.027 Uiso calc R 1 . .
    C C2 -0.2028(3) 0.10569(8) 0.41685(12) 0.0254(4) Uani d . 1 . .
    H H2 -0.3246 0.0880 0.4467 0.030 Uiso calc R 1 . .
    C C3 -0.0618(3) 0.15439(8) 0.46245(12) 0.0265(4) Uani d . 1 . .
    H H3 -0.0853 0.1700 0.5233 0.032 Uiso calc R 1 . .
    C C4 0.1138(3) 0.18002(8) 0.41821(11) 0.0236(4) Uani d . 1 . .
    H H4 0.2097 0.2140 0.4490 0.028 Uiso calc R 1 . .
    C C5 0.1543(3) 0.15732(8) 0.32926(11) 0.0192(3) Uani d . 1 . .
    C C6 0.0101(3) 0.10716(7) 0.28472(11) 0.0191(3) Uani d . 1 . .
    C C7 0.3357(3) 0.18746(7) 0.28331(11) 0.0193(3) Uani d . 1 . .
    C C8 0.4794(3) 0.24640(8) 0.32096(11) 0.0226(4) Uani d . 1 . .
    H H8A 0.5650 0.2361 0.3836 0.027 Uiso calc R 1 . .
    H H8B 0.3844 0.2870 0.3262 0.027 Uiso calc R 1 . .
    C C9 0.6421(3) 0.25620(8) 0.24635(11) 0.0206(3) Uani d . 1 . .
    H H9 0.8012 0.2441 0.2741 0.025 Uiso calc R 1 . .
    C C10 0.6398(3) 0.32637(8) 0.20576(11) 0.0200(3) Uani d . 1 . .
    C C11 0.8302(3) 0.36729(8) 0.22445(12) 0.0239(4) Uani d . 1 . .
    H H11 0.9642 0.3504 0.2609 0.029 Uiso calc R 1 . .
    C C12 0.8266(3) 0.43256(8) 0.19053(12) 0.0283(4) Uani d . 1 . .
    H H12 0.9583 0.4602 0.2036 0.034 Uiso calc R 1 . .
    C C13 0.6333(3) 0.45765(8) 0.13795(12) 0.0280(4) Uani d . 1 . .
    H H13 0.6313 0.5026 0.1151 0.034 Uiso calc R 1 . .
    C C14 0.4419(3) 0.41735(8) 0.11839(12) 0.0269(4) Uani d . 1 . .
    H H14 0.3084 0.4345 0.0818 0.032 Uiso calc R 1 . .
    C C15 0.4452(3) 0.35182(8) 0.15230(11) 0.0240(4) Uani d . 1 . .
    H H15 0.3135 0.3242 0.1389 0.029 Uiso calc R 1 . .
    C C16 0.6704(3) 0.18811(7) 0.10113(11) 0.0203(3) Uani d . 1 . .
    C C17 0.5629(3) 0.13908(7) 0.02984(10) 0.0195(3) Uani d . 1 . .
    C C18 0.3295(3) 0.13668(8) -0.00025(11) 0.0218(4) Uani d . 1 . .
    H H18 0.2325 0.1655 0.0298 0.026 Uiso calc R 1 . .
    C C20 0.3736(3) 0.05574(8) -0.10932(12) 0.0279(4) Uani d . 1 . .
    H H20 0.3080 0.0257 -0.1571 0.034 Uiso calc R 1 . .
    C C21 0.6074(3) 0.05498(8) -0.08567(12) 0.0261(4) Uani d . 1 . .
    H H21 0.7001 0.0257 -0.1171 0.031 Uiso calc R 1 . .
    C C22 0.7038(3) 0.09771(8) -0.01539(11) 0.0238(4) Uani d . 1 . .
    H H22 0.8646 0.0988 0.0018 0.029 Uiso calc R 1 . .
    N N1 0.3806(2) 0.16609(6) 0.20245(9) 0.0197(3) Uani d . 1 . .
    N N2 0.5547(2) 0.20539(6) 0.17433(9) 0.0208(3) Uani d . 1 . .
    N N3 0.2337(2) 0.09623(7) -0.06900(9) 0.0275(3) Uani d . 1 . .
    O O1 0.03606(19) 0.08124(5) 0.19886(7) 0.0237(3) Uani d . 1 . .
    H H1 0.1396 0.1024 0.1762 0.035 Uiso calc R 1 . .
    O O2 0.85361(18) 0.21517(5) 0.09370(8) 0.0248(3) 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 C2 . 1.383(2) ?
    C1 C6 . 1.389(2) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.382(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.380(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.398(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.407(2) ?
    C5 C7 . 1.456(2) ?
    C6 O1 . 1.3567(18) ?
    C7 N1 . 1.2900(19) ?
    C7 C8 . 1.502(2) ?
    C8 C9 . 1.538(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 N2 . 1.4839(19) ?
    C9 C10 . 1.508(2) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.384(2) ?
    C10 C15 . 1.389(2) ?
    C11 C12 . 1.382(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.375(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.383(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.387(2) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 O2 . 1.2247(18) ?
    C16 N2 . 1.3655(19) ?
    C16 C17 . 1.489(2) ?
    C17 C22 . 1.387(2) ?
    C17 C18 . 1.390(2) ?
    C18 N3 . 1.335(2) ?
    C18 H18 . 0.9500 ?
    C20 N3 . 1.336(2) ?
    C20 C21 . 1.378(2) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.379(2) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
    N1 N2 . 1.3906(17) ?
    O1 H1 . 0.8400 ?
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
    C2 C1 C6 . . 120.02(15) ?
    C2 C1 H1A . . 120.0 ?
    C6 C1 H1A . . 120.0 ?
    C3 C2 C1 . . 121.01(16) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C4 C3 C2 . . 118.98(15) ?
    C4 C3 H3 . . 120.5 ?
    C2 C3 H3 . . 120.5 ?
    C3 C4 C5 . . 121.71(16) ?
    C3 C4 H4 . . 119.1 ?
    C5 C4 H4 . . 119.1 ?
    C4 C5 C6 . . 118.28(15) ?
    C4 C5 C7 . . 120.06(15) ?
    C6 C5 C7 . . 121.61(14) ?
    O1 C6 C1 . . 117.08(14) ?
    O1 C6 C5 . . 122.94(14) ?
    C1 C6 C5 . . 119.98(14) ?
    N1 C7 C5 . . 121.22(14) ?
    N1 C7 C8 . . 113.80(14) ?
    C5 C7 C8 . . 124.94(13) ?
    C7 C8 C9 . . 103.02(12) ?
    C7 C8 H8A . . 111.2 ?
    C9 C8 H8A . . 111.2 ?
    C7 C8 H8B . . 111.2 ?
    C9 C8 H8B . . 111.2 ?
    H8A C8 H8B . . 109.1 ?
    N2 C9 C10 . . 112.08(12) ?
    N2 C9 C8 . . 101.67(12) ?
    C10 C9 C8 . . 114.09(13) ?
    N2 C9 H9 . . 109.6 ?
    C10 C9 H9 . . 109.6 ?
    C8 C9 H9 . . 109.6 ?
    C11 C10 C15 . . 119.06(15) ?
    C11 C10 C9 . . 120.08(14) ?
    C15 C10 C9 . . 120.82(14) ?
    C12 C11 C10 . . 120.50(16) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C13 C12 C11 . . 120.27(16) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 119.96(16) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 119.85(16) ?
    C13 C14 H14 . . 120.1 ?
    C15 C14 H14 . . 120.1 ?
    C14 C15 C10 . . 120.37(15) ?
    C14 C15 H15 . . 119.8 ?
    C10 C15 H15 . . 119.8 ?
    O2 C16 N2 . . 119.51(14) ?
    O2 C16 C17 . . 121.97(14) ?
    N2 C16 C17 . . 118.45(13) ?
    C22 C17 C18 . . 117.81(15) ?
    C22 C17 C16 . . 118.51(14) ?
    C18 C17 C16 . . 123.41(14) ?
    N3 C18 C17 . . 123.75(15) ?
    N3 C18 H18 . . 118.1 ?
    C17 C18 H18 . . 118.1 ?
    N3 C20 C21 . . 123.88(16) ?
    N3 C20 H20 . . 118.1 ?
    C21 C20 H20 . . 118.1 ?
    C20 C21 C22 . . 118.45(15) ?
    C20 C21 H21 . . 120.8 ?
    C22 C21 H21 . . 120.8 ?
    C21 C22 C17 . . 119.20(15) ?
    C21 C22 H22 . . 120.4 ?
    C17 C22 H22 . . 120.4 ?
    C7 N1 N2 . . 108.71(13) ?
    C16 N2 N1 . . 122.91(12) ?
    C16 N2 C9 . . 122.53(12) ?
    N1 N2 C9 . . 112.57(11) ?
    C18 N3 C20 . . 116.89(14) ?
    C6 O1 H1 . . 109.5 ?
