##############################################################################
###                                                                        ###
###        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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-10-10
_journal_date_accepted     2005-10-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     11
_journal_page_first     o3862
_journal_page_last     o3863
_journal_paper_category     EO
_journal_coeditor_code     HK6045
_publ_contact_author_name     'Jiang-Sheng Li'
_publ_contact_author_address
; School of Chemical Engineering & Technology, Tianjin University
  Tianjin 300072
  People's Republic of China
;
_publ_contact_author_email     jansenlee1103@yahoo.com.cn
_publ_contact_author_fax     '8622 2740 6314'
_publ_contact_author_phone     '8622 2740 6314'
_publ_section_title
;
1,3-Diphenyl-1H-pyrazol-5-yl 4-chlorobenzoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li, Jiang-Sheng' .
;
School of Chemical Engineering & Technology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Duan, Xue-Min' .
;
School of Pharmacy
Jiangxi Science & Technology Normal University
Nanchang 330013
People's Republic of China
;
    'Huang, Peng-Mian' .
;
School of Chemical Engineering & Technology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Zeng, Tao' .
;
School of Chemical Engineering & Technology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Fan, Mei-Lian' .
;
School of Chemical Engineering & Technology
Tianjin University
Tianjin 300072
People's Republic of China
;
data_I
_chemical_name_systematic
;
1,3-diphenyl-1H-pyrazol-5-yl 4-chlorobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H15 Cl N2 O2'
_chemical_formula_sum     'C22 H15 Cl N2 O2'
_chemical_formula_iupac     'C22 H15 Cl N2 O2'
_chemical_formula_weight     374.81
_chemical_melting_point     398.8-399.9
_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     7.934(3)
_cell_length_b     10.607(4)
_cell_length_c     11.752(4)
_cell_angle_alpha     80.890(5)
_cell_angle_beta     75.500(6)
_cell_angle_gamma     72.550(6)
_cell_volume     909.6(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1612
_cell_measurement_theta_min     2.58
_cell_measurement_theta_max     24.88
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.368
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     388
_exptl_absorpt_coefficient_mu     0.230
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.932
_exptl_absorpt_correction_T_max     0.955
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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_detector_area_resol_mean     ?
_diffrn_reflns_number     4664
_diffrn_reflns_av_R_equivalents     0.0358
_diffrn_reflns_av_sigmaI/netI     0.0535
_diffrn_reflns_theta_min     1.80
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_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     3195
_reflns_number_gt     2173
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0713
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.0935
_refine_ls_wR_factor_ref     0.1123
_refine_ls_goodness_of_fit_ref     1.033
_refine_ls_restrained_S_all     1.033
_refine_ls_number_reflns     3195
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0452P)²+0.2055P] 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     0.003
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.131
_refine_diff_density_min     -0.253
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART, (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL, (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    Cl1 0.16366(10) 0.69599(7) 0.59198(6) 0.0818(3) Uani d . 1 . . Cl
    O1 0.61222(19) 0.14367(13) 0.85171(12) 0.0473(4) Uani d . 1 . . O
    O2 0.5816(2) 0.27743(15) 0.99086(13) 0.0548(4) Uani d . 1 . . O
    N1 0.7494(2) -0.08017(17) 0.85447(14) 0.0439(4) Uani d . 1 . . N
    N2 0.8346(2) -0.18688(17) 0.92006(15) 0.0476(5) Uani d . 1 . . N
    C1 0.7200(3) -0.0975(2) 0.74335(18) 0.0419(5) Uani d . 1 . . C
    C2 0.7692(3) -0.0174(2) 0.64386(19) 0.0505(6) Uani d . 1 . . C
    H2 0.8186 0.0502 0.6489 0.061 Uiso calc R 1 . . H
    C3 0.7450(3) -0.0381(2) 0.5366(2) 0.0588(6) Uani d . 1 . . C
    H3 0.7771 0.0162 0.4693 0.071 Uiso calc R 1 . . H
    C4 0.6735(3) -0.1390(3) 0.5295(2) 0.0597(7) Uani d . 1 . . C
    H4 0.6578 -0.1533 0.4572 0.072 Uiso calc R 1 . . H
    C5 0.6253(3) -0.2184(3) 0.6284(2) 0.0593(7) Uani d . 1 . . C
    H5 0.5775 -0.2866 0.6229 0.071 Uiso calc R 1 . . H
    C6 0.6470(3) -0.1982(2) 0.73700(19) 0.0511(6) Uani d . 1 . . C
    H6 0.6130 -0.2517 0.8044 0.061 Uiso calc R 1 . . H
    C7 0.8407(3) -0.1375(2) 1.01575(17) 0.0396(5) Uani d . 1 . . C
    C8 0.9278(3) -0.2268(2) 1.10658(17) 0.0407(5) Uani d . 1 . . C
    C9 1.0001(3) -0.3617(2) 1.09294(19) 0.0492(6) Uani d . 1 . . C
    H9 0.9930 -0.3945 1.0259 0.059 Uiso calc R 1 . . H
    C10 1.0813(3) -0.4474(2) 1.1759(2) 0.0577(6) Uani d . 1 . . C
    H10 1.1283 -0.5372 1.1648 0.069 Uiso calc R 1 . . H
    C11 1.0937(3) -0.4012(3) 1.2758(2) 0.0591(7) Uani d . 1 . . C
    H11 1.1485 -0.4592 1.3324 0.071 Uiso calc R 1 . . H
    C12 1.0240(3) -0.2677(3) 1.2908(2) 0.0589(6) Uani d . 1 . . C
    H12 1.0327 -0.2356 1.3577 0.071 Uiso calc R 1 . . H
    C13 0.9414(3) -0.1813(2) 1.20741(19) 0.0511(6) Uani d . 1 . . C
    H13 0.8944 -0.0916 1.2190 0.061 Uiso calc R 1 . . H
    C14 0.7586(3) 0.0001(2) 1.01370(18) 0.0435(5) Uani d . 1 . . C
    H14 0.7456 0.0564 1.0703 0.052 Uiso calc R 1 . . H
    C15 0.7028(3) 0.0317(2) 0.91014(17) 0.0399(5) Uani d . 1 . . C
    C16 0.5554(3) 0.2634(2) 0.89877(18) 0.0398(5) Uani d . 1 . . C
    C17 0.4616(3) 0.36804(19) 0.81935(17) 0.0377(5) Uani d . 1 . . C
    C18 0.3850(3) 0.4942(2) 0.85712(19) 0.0462(5) Uani d . 1 . . C
    H18 0.3951 0.5106 0.9302 0.055 Uiso calc R 1 . . H
    C19 0.2942(3) 0.5952(2) 0.7876(2) 0.0525(6) Uani d . 1 . . C
    H19 0.2425 0.6796 0.8134 0.063 Uiso calc R 1 . . H
    C20 0.2806(3) 0.5700(2) 0.6793(2) 0.0493(6) Uani d . 1 . . C
    C21 0.3560(3) 0.4456(2) 0.6400(2) 0.0543(6) Uani d . 1 . . C
    H21 0.3461 0.4301 0.5666 0.065 Uiso calc R 1 . . H
    C22 0.4460(3) 0.3444(2) 0.70994(18) 0.0476(6) Uani d . 1 . . C
    H22 0.4966 0.2601 0.6840 0.057 Uiso calc R 1 . . H
_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
    Cl1 C20 . 1.732(2) ?
    O1 C15 . 1.370(2) ?
    O1 C16 . 1.370(2) ?
    O2 C16 . 1.191(2) ?
    N1 C15 . 1.354(3) ?
    N1 N2 . 1.363(2) ?
    N1 C1 . 1.431(2) ?
    N2 C7 . 1.330(2) ?
    C1 C2 . 1.377(3) ?
    C1 C6 . 1.379(3) ?
    C2 C3 . 1.381(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.376(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.366(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.386(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C14 . 1.408(3) ?
    C7 C8 . 1.473(3) ?
    C8 C13 . 1.388(3) ?
    C8 C9 . 1.392(3) ?
    C9 C10 . 1.369(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.377(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.379(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.381(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.357(3) ?
    C14 H14 . 0.9300 ?
    C16 C17 . 1.477(3) ?
    C17 C18 . 1.386(3) ?
    C17 C22 . 1.390(3) ?
    C18 C19 . 1.375(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.376(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.376(3) ?
    C21 C22 . 1.376(3) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 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
    C15 O1 C16 . . 120.88(15) ?
    C15 N1 N2 . . 110.80(16) ?
    C15 N1 C1 . . 129.41(17) ?
    N2 N1 C1 . . 119.79(16) ?
    C7 N2 N1 . . 104.64(16) ?
    C2 C1 C6 . . 120.70(19) ?
    C2 C1 N1 . . 120.42(19) ?
    C6 C1 N1 . . 118.85(19) ?
    C1 C2 C3 . . 119.7(2) ?
    C1 C2 H2 . . 120.2 ?
    C3 C2 H2 . . 120.2 ?
    C4 C3 C2 . . 119.9(2) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C5 C4 C3 . . 120.1(2) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.7(2) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C1 C6 C5 . . 118.8(2) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    N2 C7 C14 . . 111.92(18) ?
    N2 C7 C8 . . 119.33(18) ?
    C14 C7 C8 . . 128.75(18) ?
    C13 C8 C9 . . 117.7(2) ?
    C13 C8 C7 . . 122.22(19) ?
    C9 C8 C7 . . 120.10(18) ?
    C10 C9 C8 . . 121.5(2) ?
    C10 C9 H9 . . 119.2 ?
    C8 C9 H9 . . 119.2 ?
    C9 C10 C11 . . 120.3(2) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C10 C11 C12 . . 119.2(2) ?
    C10 C11 H11 . . 120.4 ?
    C12 C11 H11 . . 120.4 ?
    C11 C12 C13 . . 120.6(2) ?
    C11 C12 H12 . . 119.7 ?
    C13 C12 H12 . . 119.7 ?
    C12 C13 C8 . . 120.7(2) ?
    C12 C13 H13 . . 119.7 ?
    C8 C13 H13 . . 119.7 ?
    C15 C14 C7 . . 104.11(18) ?
    C15 C14 H14 . . 127.9 ?
    C7 C14 H14 . . 127.9 ?
    N1 C15 C14 . . 108.52(18) ?
    N1 C15 O1 . . 114.82(17) ?
    C14 C15 O1 . . 136.65(18) ?
    O2 C16 O1 . . 123.06(19) ?
    O2 C16 C17 . . 126.47(19) ?
    O1 C16 C17 . . 110.47(16) ?
    C18 C17 C22 . . 119.28(19) ?
    C18 C17 C16 . . 118.03(17) ?
    C22 C17 C16 . . 122.68(18) ?
    C19 C18 C17 . . 120.66(19) ?
    C19 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
    C20 C19 C18 . . 119.2(2) ?
    C20 C19 H19 . . 120.4 ?
    C18 C19 H19 . . 120.4 ?
    C19 C20 C21 . . 121.1(2) ?
    C19 C20 Cl1 . . 119.60(18) ?
    C21 C20 Cl1 . . 119.30(18) ?
    C20 C21 C22 . . 119.6(2) ?
    C20 C21 H21 . . 120.2 ?
    C22 C21 H21 . . 120.2 ?
    C21 C22 C17 . . 120.1(2) ?
    C21 C22 H22 . . 119.9 ?
    C17 C22 H22 . . 119.9 ?
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
    C15 N1 N2 C7 . . . . -0.7(2) ?
    C1 N1 N2 C7 . . . . 179.78(18) ?
    C15 N1 C1 C2 . . . . 51.0(3) ?
    N2 N1 C1 C2 . . . . -129.6(2) ?
    C15 N1 C1 C6 . . . . -131.1(2) ?
    N2 N1 C1 C6 . . . . 48.3(3) ?
    C6 C1 C2 C3 . . . . 0.1(3) ?
    N1 C1 C2 C3 . . . . 178.0(2) ?
    C1 C2 C3 C4 . . . . -0.6(3) ?
    C2 C3 C4 C5 . . . . 0.4(4) ?
    C3 C4 C5 C6 . . . . 0.3(4) ?
    C2 C1 C6 C5 . . . . 0.5(3) ?
    N1 C1 C6 C5 . . . . -177.4(2) ?
    C4 C5 C6 C1 . . . . -0.7(4) ?
    N1 N2 C7 C14 . . . . 0.6(2) ?
    N1 N2 C7 C8 . . . . -179.10(17) ?
    N2 C7 C8 C13 . . . . 178.86(19) ?
    C14 C7 C8 C13 . . . . -0.8(3) ?
    N2 C7 C8 C9 . . . . -1.1(3) ?
    C14 C7 C8 C9 . . . . 179.2(2) ?
    C13 C8 C9 C10 . . . . 0.3(3) ?
    C7 C8 C9 C10 . . . . -179.8(2) ?
    C8 C9 C10 C11 . . . . -0.1(4) ?
    C9 C10 C11 C12 . . . . -0.2(4) ?
    C10 C11 C12 C13 . . . . 0.5(4) ?
    C11 C12 C13 C8 . . . . -0.4(4) ?
    C9 C8 C13 C12 . . . . 0.0(3) ?
    C7 C8 C13 C12 . . . . -180.0(2) ?
    N2 C7 C14 C15 . . . . -0.3(2) ?
    C8 C7 C14 C15 . . . . 179.4(2) ?
    N2 N1 C15 C14 . . . . 0.5(2) ?
    C1 N1 C15 C14 . . . . -180.0(2) ?
    N2 N1 C15 O1 . . . . -178.50(16) ?
    C1 N1 C15 O1 . . . . 1.0(3) ?
    C7 C14 C15 N1 . . . . -0.2(2) ?
    C7 C14 C15 O1 . . . . 178.6(2) ?
    C16 O1 C15 N1 . . . . 179.31(17) ?
    C16 O1 C15 C14 . . . . 0.6(4) ?
    C15 O1 C16 O2 . . . . 0.5(3) ?
    C15 O1 C16 C17 . . . . -179.97(17) ?
    O2 C16 C17 C18 . . . . -4.5(3) ?
    O1 C16 C17 C18 . . . . 175.94(18) ?
    O2 C16 C17 C22 . . . . 176.2(2) ?
    O1 C16 C17 C22 . . . . -3.3(3) ?
    C22 C17 C18 C19 . . . . 0.1(3) ?
    C16 C17 C18 C19 . . . . -179.25(19) ?
    C17 C18 C19 C20 . . . . -0.3(3) ?
    C18 C19 C20 C21 . . . . 0.2(3) ?
    C18 C19 C20 Cl1 . . . . 179.05(17) ?
    C19 C20 C21 C22 . . . . 0.2(4) ?
    Cl1 C20 C21 C22 . . . . -178.72(17) ?
    C20 C21 C22 C17 . . . . -0.4(3) ?
    C18 C17 C22 C21 . . . . 0.3(3) ?
    C16 C17 C22 C21 . . . . 179.55(19) ?
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
    C6 H6 O2 2_657 0.93 2.54 3.373(3) 150 yes
    C9 H9 N2 . 0.93 2.50 2.823(3) 101 yes
    C14 H14 O2 . 0.93 2.48 2.856(3) 104 yes
    C22 H22 O1 . 0.93 2.39 2.709(3) 100 yes
