##############################################################################
###                                                                        ###
###        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/  #
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data_global
_audit_creation_method     'SHELXL and local programs'
_journal_date_recd_electronic     2010-09-08
_journal_date_accepted     2010-09-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     o2649
_journal_page_last     o2649
_journal_paper_category     QO
_journal_coeditor_code     RZ2487
_publ_contact_author_name     'Lynne S. Taylor'
_publ_contact_author_address
;
Department of Industrial and Physical Pharmacy, Purdue University,
575 Stadium Mall Drive, West Lafayette, IN 47907, USA
;
_publ_contact_author_email     'lstaylor@purdue.edu'
_publ_contact_author_fax     '+1 (765) 496-6614'
_publ_contact_author_phone     '+1 (765) 494-6545'
_publ_section_title
;
1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole (bifonazole)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Van Eerdenbrugh, Bernard' .
;
Department of Industrial and Physical Pharmacy, Purdue University,
575 Stadium Mall Drive, West Lafayette, IN 47907, USA
and
Laboratory for Pharmacotechnology and Biopharmacy,
K.U. Leuven, Gasthuisberg O&N2, Herestraat 49, Box 921, 3000, Leuven, Belgium
;
    'Fanwick, Phillip E.' .
;
Department of Chemistry, Purdue University,
560 Oval Drive, West Lafayette, IN 47907, USA
;
    'Taylor, Lynne S.' .
;
Department of Industrial and Physical Pharmacy, Purdue University,
575 Stadium Mall Drive, West Lafayette, IN 47907, USA
;
data_I
_chemical_name_systematic
;
1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole
;
_chemical_name_common     'bifonazole'
_chemical_formula_moiety     'C22 H18 N2'
_chemical_formula_sum     'C22 H18 N2'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C22 H18 N2'
_chemical_formula_weight     310.40
_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     7.9737(7)
_cell_length_b     6.2591(6)
_cell_length_c     33.265(3)
_cell_angle_alpha     90.00
_cell_angle_beta     93.805(8)
_cell_angle_gamma     90.00
_cell_volume     1656.5(3)
_cell_formula_units_z     4
_cell_measurement_reflns_used     3380
_cell_measurement_theta_min     2
_cell_measurement_theta_max     71
_cell_measurement_temperature     150.0(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.245
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.564
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.8595
_exptl_absorpt_correction_T_max     0.9790
_diffrn_ambient_temperature     150.0(2)
_diffrn_radiation_type     Cu-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     'confocal optics'
_diffrn_measurement_device_type     'Rigaku Rapid II'
_diffrn_measurement_method     ω
_diffrn_reflns_number     19391
_diffrn_reflns_av_R_equivalents     0.0300
_diffrn_reflns_av_sigmaI/netI     0.0145
_diffrn_reflns_theta_min     2.66
_diffrn_reflns_theta_max     71.76
_diffrn_reflns_theta_full     71.8
_diffrn_measured_fraction_theta_max     0.9420
_diffrn_measured_fraction_theta_full     0.9420
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -40
_diffrn_reflns_limit_l_max     40
_diffrn_standards_number     0
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Outlier data were removed using a local program based on the method of Prince
and Nicholson.
Refinement on F² for ALL reflections except for 0 with very negative
F² or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F², conventional R-factors R are based on F,
with F set to zero for negative F². The observed criterion of
F² > σ(F²) is used only for calculating R_factor_obs
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     3064
_reflns_number_gt     2801
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.044
_refine_ls_R_factor_gt     0.041
_refine_ls_wR_factor_gt     0.104
_refine_ls_wR_factor_ref     0.107
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_number_reflns     3064
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0501P)²+0.7321P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_diff_density_max     0.19
_refine_diff_density_min     -0.20
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.20E-02
loop_
    _atom_type_symbol
    N
    C
    H
_atom_type_scat_source     'International Tables for Crystallography (Vol C)'
_computing_data_collection     'CrystalClear (Rigaku, 2001)'
_computing_cell_refinement     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                               'ORTEPII (Johnson, 1976) and PLATON (Spek, 2009)'
_computing_publication_material
                                 'SHELXL97 (Sheldrick, 2008) and local programs'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.15014(12) 0.10641(19) 0.07667(3) 0.0251(3) Uani Uani d . 1 . .
    N N2 0.26374(14) -0.2162(2) 0.07143(3) 0.0316(3) Uani Uani d . 1 . .
    C C1 -0.10284(15) 0.3342(2) 0.07936(4) 0.0247(3) Uani Uani d . 1 . .
    C C2 -0.21816(16) 0.1678(2) 0.08086(4) 0.0277(3) Uani Uani d . 1 . .
    C C3 -0.38706(16) 0.2022(2) 0.06900(4) 0.0313(3) Uani Uani d . 1 . .
    C C4 -0.44051(16) 0.4013(3) 0.05515(4) 0.0322(3) Uani Uani d . 1 . .
    C C5 -0.32601(17) 0.5661(2) 0.05271(4) 0.0324(3) Uani Uani d . 1 . .
    C C6 -0.15719(16) 0.5331(2) 0.06485(4) 0.0291(3) Uani Uani d . 1 . .
    C C7 0.08225(15) 0.3066(2) 0.09321(4) 0.0247(3) Uani Uani d . 1 . .
    C C8 0.12033(15) 0.3155(2) 0.13881(4) 0.0245(3) Uani Uani d . 1 . .
    C C9 0.02747(16) 0.2044(2) 0.16633(4) 0.0288(3) Uani Uani d . 1 . .
    C C10 0.07544(16) 0.2074(2) 0.20723(4) 0.0290(3) Uani Uani d . 1 . .
    C C11 0.21664(15) 0.3221(2) 0.22243(4) 0.0262(3) Uani Uani d . 1 . .
    C C12 0.30588(16) 0.4380(2) 0.19481(4) 0.0288(3) Uani Uani d . 1 . .
    C C13 0.25869(16) 0.4334(2) 0.15381(4) 0.0276(3) Uani Uani d . 1 . .
    C C14 0.27240(15) 0.3177(2) 0.26618(4) 0.0266(3) Uani Uani d . 1 . .
    C C15 0.36722(17) 0.4845(2) 0.28421(4) 0.0318(3) Uani Uani d . 1 . .
    C C16 0.42239(18) 0.4754(3) 0.32482(4) 0.0350(3) Uani Uani d . 1 . .
    C C17 0.38402(17) 0.3018(2) 0.34818(4) 0.0319(3) Uani Uani d . 1 . .
    C C18 0.28887(17) 0.1358(3) 0.33100(4) 0.0342(3) Uani Uani d . 1 . .
    C C19 0.23430(17) 0.1436(2) 0.29038(4) 0.0324(3) Uani Uani d . 1 . .
    C C20 0.21208(16) -0.0692(2) 0.09636(4) 0.0283(3) Uani Uani d . 1 . .
    C C21 0.23282(16) -0.1299(2) 0.03361(4) 0.0316(3) Uani Uani d . 1 . .
    C C22 0.16304(17) 0.0681(2) 0.03627(4) 0.0314(3) Uani Uani d . 1 . .
    H H2 -0.1817 0.0306 0.0900 0.033 Uiso Uiso calc R 1 . .
    H H3 -0.4657 0.0888 0.0704 0.038 Uiso Uiso calc R 1 . .
    H H4 -0.5558 0.4246 0.0473 0.039 Uiso Uiso calc R 1 . .
    H H5 -0.3624 0.7018 0.0428 0.039 Uiso Uiso calc R 1 . .
    H H6 -0.0789 0.6467 0.0632 0.035 Uiso Uiso calc R 1 . .
    H H7 0.1445 0.4277 0.0814 0.030 Uiso Uiso calc R 1 . .
    H H9 -0.0694 0.1261 0.1569 0.035 Uiso Uiso calc R 1 . .
    H H10 0.0110 0.1299 0.2253 0.035 Uiso Uiso calc R 1 . .
    H H12 0.4002 0.5210 0.2042 0.035 Uiso Uiso calc R 1 . .
    H H13 0.3221 0.5123 0.1357 0.033 Uiso Uiso calc R 1 . .
    H H15 0.3942 0.6052 0.2686 0.038 Uiso Uiso calc R 1 . .
    H H16 0.4870 0.5896 0.3366 0.042 Uiso Uiso calc R 1 . .
    H H17 0.4225 0.2962 0.3758 0.038 Uiso Uiso calc R 1 . .
    H H18 0.2609 0.0167 0.3469 0.041 Uiso Uiso calc R 1 . .
    H H19 0.1699 0.0286 0.2789 0.039 Uiso Uiso calc R 1 . .
    H H20 0.2177 -0.0849 0.1248 0.034 Uiso Uiso calc R 1 . .
    H H21 0.2567 -0.1985 0.0092 0.038 Uiso Uiso calc R 1 . .
    H H22 0.1300 0.1609 0.0146 0.038 Uiso Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C20 . . 1.3560(17) ?
    N1 C22 . . 1.3758(17) ?
    N1 C7 . . 1.4854(17) ?
    N2 C20 . . 1.3226(18) ?
    N2 C21 . . 1.3765(18) ?
    C1 C2 . . 1.3921(19) ?
    C1 C6 . . 1.3940(19) ?
    C1 C7 . . 1.5263(16) ?
    C2 C3 . . 1.3947(18) ?
    C2 H2 . . 0.9500 ?
    C3 C4 . . 1.386(2) ?
    C3 H3 . . 0.9500 ?
    C4 C5 . . 1.384(2) ?
    C4 H4 . . 0.9500 ?
    C5 C6 . . 1.3949(19) ?
    C5 H5 . . 0.9500 ?
    C6 H6 . . 0.9500 ?
    C7 C8 . . 1.5280(17) ?
    C7 H7 . . 1.0000 ?
    C8 C13 . . 1.3921(18) ?
    C8 C9 . . 1.4000(19) ?
    C9 C10 . . 1.3887(18) ?
    C9 H9 . . 0.9500 ?
    C10 C11 . . 1.4011(18) ?
    C10 H10 . . 0.9500 ?
    C11 C12 . . 1.4012(19) ?
    C11 C14 . . 1.4935(18) ?
    C12 C13 . . 1.3907(18) ?
    C12 H12 . . 0.9500 ?
    C13 H13 . . 0.9500 ?
    C14 C19 . . 1.400(2) ?
    C14 C15 . . 1.4005(19) ?
    C15 C16 . . 1.3939(19) ?
    C15 H15 . . 0.9500 ?
    C16 C17 . . 1.381(2) ?
    C16 H16 . . 0.9500 ?
    C17 C18 . . 1.387(2) ?
    C17 H17 . . 0.9500 ?
    C18 C19 . . 1.3928(19) ?
    C18 H18 . . 0.9500 ?
    C19 H19 . . 0.9500 ?
    C20 H20 . . 0.9500 ?
    C21 C22 . . 1.364(2) ?
    C21 H21 . . 0.9500 ?
    C22 H22 . . 0.9500 ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C20 N1 C22 . . . 106.39(11) ?
    C20 N1 C7 . . . 129.43(11) ?
    C22 N1 C7 . . . 124.18(11) ?
    C20 N2 C21 . . . 104.82(12) ?
    C2 C1 C6 . . . 119.30(11) ?
    C2 C1 C7 . . . 122.18(12) ?
    C6 C1 C7 . . . 118.52(12) ?
    C1 C2 C3 . . . 120.16(13) ?
    C1 C2 H2 . . . 119.90 ?
    C3 C2 H2 . . . 119.90 ?
    C4 C3 C2 . . . 120.16(13) ?
    C4 C3 H3 . . . 119.90 ?
    C2 C3 H3 . . . 119.90 ?
    C5 C4 C3 . . . 120.03(12) ?
    C5 C4 H4 . . . 120.00 ?
    C3 C4 H4 . . . 120.00 ?
    C4 C5 C6 . . . 120.02(13) ?
    C4 C5 H5 . . . 120.00 ?
    C6 C5 H5 . . . 120.00 ?
    C1 C6 C5 . . . 120.30(13) ?
    C1 C6 H6 . . . 119.80 ?
    C5 C6 H6 . . . 119.80 ?
    N1 C7 C1 . . . 110.62(10) ?
    N1 C7 C8 . . . 110.18(10) ?
    C1 C7 C8 . . . 114.84(10) ?
    N1 C7 H7 . . . 106.90 ?
    C1 C7 H7 . . . 106.90 ?
    C8 C7 H7 . . . 106.90 ?
    C13 C8 C9 . . . 118.03(12) ?
    C13 C8 C7 . . . 118.39(11) ?
    C9 C8 C7 . . . 123.53(11) ?
    C10 C9 C8 . . . 120.71(12) ?
    C10 C9 H9 . . . 119.60 ?
    C8 C9 H9 . . . 119.60 ?
    C9 C10 C11 . . . 121.53(12) ?
    C9 C10 H10 . . . 119.20 ?
    C11 C10 H10 . . . 119.20 ?
    C10 C11 C12 . . . 117.35(12) ?
    C10 C11 C14 . . . 121.48(12) ?
    C12 C11 C14 . . . 121.16(12) ?
    C13 C12 C11 . . . 121.09(12) ?
    C13 C12 H12 . . . 119.50 ?
    C11 C12 H12 . . . 119.50 ?
    C12 C13 C8 . . . 121.25(12) ?
    C12 C13 H13 . . . 119.40 ?
    C8 C13 H13 . . . 119.40 ?
    C19 C14 C15 . . . 117.75(12) ?
    C19 C14 C11 . . . 120.86(12) ?
    C15 C14 C11 . . . 121.38(12) ?
    C16 C15 C14 . . . 120.74(14) ?
    C16 C15 H15 . . . 119.60 ?
    C14 C15 H15 . . . 119.60 ?
    C17 C16 C15 . . . 120.66(14) ?
    C17 C16 H16 . . . 119.70 ?
    C15 C16 H16 . . . 119.70 ?
    C16 C17 C18 . . . 119.52(13) ?
    C16 C17 H17 . . . 120.20 ?
    C18 C17 H17 . . . 120.20 ?
    C17 C18 C19 . . . 120.02(14) ?
    C17 C18 H18 . . . 120.00 ?
    C19 C18 H18 . . . 120.00 ?
    C18 C19 C14 . . . 121.31(13) ?
    C18 C19 H19 . . . 119.30 ?
    C14 C19 H19 . . . 119.30 ?
    N2 C20 N1 . . . 112.32(12) ?
    N2 C20 H20 . . . 123.80 ?
    N1 C20 H20 . . . 123.80 ?
    C22 C21 N2 . . . 110.27(12) ?
    C22 C21 H21 . . . 124.90 ?
    N2 C21 H21 . . . 124.90 ?
    C21 C22 N1 . . . 106.21(12) ?
    C21 C22 H22 . . . 126.90 ?
    N1 C22 H22 . . . 126.90 ?
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
    C6 C1 C2 C3 . . . . -1.77(19) ?
    C7 C1 C2 C3 . . . . 178.09(12) ?
    C1 C2 C3 C4 . . . . 0.9(2) ?
    C2 C3 C4 C5 . . . . 0.6(2) ?
    C3 C4 C5 C6 . . . . -1.1(2) ?
    C2 C1 C6 C5 . . . . 1.24(19) ?
    C7 C1 C6 C5 . . . . -178.63(12) ?
    C4 C5 C6 C1 . . . . 0.2(2) ?
    C20 N1 C7 C1 . . . . -116.94(13) ?
    C22 N1 C7 C1 . . . . 63.98(15) ?
    C20 N1 C7 C8 . . . . 11.12(17) ?
    C22 N1 C7 C8 . . . . -167.95(11) ?
    C2 C1 C7 N1 . . . . 46.28(16) ?
    C6 C1 C7 N1 . . . . -133.85(12) ?
    C2 C1 C7 C8 . . . . -79.20(15) ?
    C6 C1 C7 C8 . . . . 100.67(14) ?
    N1 C7 C8 C13 . . . . 98.12(14) ?
    C1 C7 C8 C13 . . . . -136.18(12) ?
    N1 C7 C8 C9 . . . . -79.26(15) ?
    C1 C7 C8 C9 . . . . 46.44(18) ?
    C13 C8 C9 C10 . . . . -1.8(2) ?
    C7 C8 C9 C10 . . . . 175.57(12) ?
    C8 C9 C10 C11 . . . . 0.5(2) ?
    C9 C10 C11 C12 . . . . 1.4(2) ?
    C9 C10 C11 C14 . . . . -177.33(12) ?
    C10 C11 C12 C13 . . . . -1.9(2) ?
    C14 C11 C12 C13 . . . . 176.77(12) ?
    C11 C12 C13 C8 . . . . 0.6(2) ?
    C9 C8 C13 C12 . . . . 1.3(2) ?
    C7 C8 C13 C12 . . . . -176.27(12) ?
    C10 C11 C14 C19 . . . . 25.82(19) ?
    C12 C11 C14 C19 . . . . -152.84(13) ?
    C10 C11 C14 C15 . . . . -155.53(13) ?
    C12 C11 C14 C15 . . . . 25.82(19) ?
    C19 C14 C15 C16 . . . . 0.5(2) ?
    C11 C14 C15 C16 . . . . -178.19(12) ?
    C14 C15 C16 C17 . . . . -0.3(2) ?
    C15 C16 C17 C18 . . . . -0.3(2) ?
    C16 C17 C18 C19 . . . . 0.7(2) ?
    C17 C18 C19 C14 . . . . -0.5(2) ?
    C15 C14 C19 C18 . . . . -0.1(2) ?
    C11 C14 C19 C18 . . . . 178.57(12) ?
    C21 N2 C20 N1 . . . . -0.11(15) ?
    C22 N1 C20 N2 . . . . 0.13(15) ?
    C7 N1 C20 N2 . . . . -179.07(11) ?
    C20 N2 C21 C22 . . . . 0.04(15) ?
    N2 C21 C22 N1 . . . . 0.03(15) ?
    C20 N1 C22 C21 . . . . -0.09(14) ?
    C7 N1 C22 C21 . . . . 179.16(11) ?
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
    C7 H7 N2 1_565 1.00 2.45 3.418(2) 161
    C3 H3 Cg1 1_655 0.95 2.76 3.609(2) 149
    C6 H6 Cg1 1_545 0.95 2.96 3.900(3) 171
    C18 H18 Cg2 2_555 0.95 3.01 3.797(7) 141
    C21 H21 Cg2 3_555 0.95 2.76 3.694(7) 170
    C12 H12 Cg3 2_645 0.95 2.87 3.737(5) 153
