##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Hydroxy-4,4-diphenylbutan-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 O2'
_chemical_formula_sum     'C16 H16 O2'
_chemical_formula_iupac     'C16 H16 O2'
_chemical_formula_weight     240.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.8619(2)
_cell_length_b     9.2015(2)
_cell_length_c     14.3720(3)
_cell_angle_alpha     90.00
_cell_angle_beta     102.098(2)
_cell_angle_gamma     90.00
_cell_volume     1275.21(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3618
_cell_measurement_theta_min     2.8915
_cell_measurement_theta_max     28.7165
_cell_measurement_temperature     150(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.252
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_absorpt_correction_T_min     0.933
_exptl_absorpt_correction_T_max     0.984
_exptl_special_details
;
Crystal cleaved from larger prism.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     16.0774
_diffrn_reflns_number     7361
_diffrn_reflns_av_R_equivalents     0.0207
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     2.90
_diffrn_reflns_theta_max     28.79
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.880
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_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     2935
_reflns_number_gt     2144
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0542
_refine_ls_R_factor_gt     0.0362
_refine_ls_wR_factor_gt     0.0631
_refine_ls_wR_factor_ref     0.0657
_refine_ls_goodness_of_fit_ref     1.009
_refine_ls_restrained_S_all     1.011
_refine_ls_number_reflns     2935
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'calc w=1/[σ²(Fo²)+(0.01P)²+0.4P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.219
_refine_diff_density_min     -0.199
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2007)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_structure_solution     'SIR97 (Altomare et al. 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2006)
;
_computing_publication_material     'publCIF (Westrip, 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 0.55546(14) 0.14657(15) 0.76771(9) 0.0373(3) Uani d . 1 . .
    H H1A 0.6047 0.0538 0.7694 0.056 Uiso calc R 1 . .
    H H1B 0.6224 0.2266 0.7750 0.056 Uiso calc R 1 . .
    H H1C 0.4896 0.1562 0.7067 0.056 Uiso calc R 1 . .
    C C2 0.47849(12) 0.15136(14) 0.84736(8) 0.0276(3) Uani d . 1 . .
    C C3 0.42255(12) 0.29752(13) 0.86860(8) 0.0256(3) Uani d . 1 . .
    H H3A 0.3802 0.3449 0.8076 0.031 Uiso calc R 1 . .
    H H3B 0.5012 0.3589 0.9004 0.031 Uiso calc R 1 . .
    C C4 0.31411(11) 0.29285(13) 0.93164(7) 0.0224(2) Uani d . 1 . .
    C C5 0.27448(11) 0.44508(13) 0.95954(8) 0.0227(2) Uani d . 1 . .
    C C6 0.30596(13) 0.57091(14) 0.91585(8) 0.0294(3) Uani d . 1 . .
    H H6 0.3561 0.5648 0.8663 0.035 Uiso calc R 1 . .
    C C7 0.26527(13) 0.70651(14) 0.94343(9) 0.0328(3) Uani d . 1 . .
    H H7 0.2875 0.7920 0.9127 0.039 Uiso calc R 1 . .
    C C8 0.19261(12) 0.71662(14) 1.01542(8) 0.0311(3) Uani d . 1 . .
    H H8 0.1649 0.8089 1.0345 0.037 Uiso calc R 1 . .
    C C9 0.16028(13) 0.59169(15) 1.05965(9) 0.0330(3) Uani d . 1 . .
    H H9 0.1100 0.5983 1.1091 0.040 Uiso calc R 1 . .
    C C10 0.20081(13) 0.45708(14) 1.03224(8) 0.0291(3) Uani d . 1 . .
    H H10 0.1783 0.3719 1.0632 0.035 Uiso calc R 1 . .
    C C11 0.18229(11) 0.21520(13) 0.87881(7) 0.0221(2) Uani d . 1 . .
    C C12 0.10703(12) 0.27142(14) 0.79318(8) 0.0282(3) Uani d . 1 . .
    H H12 0.1379 0.3576 0.7677 0.034 Uiso calc R 1 . .
    C C13 -0.01221(13) 0.20283(15) 0.74497(8) 0.0336(3) Uani d . 1 . .
    H H13 -0.0627 0.2423 0.6869 0.040 Uiso calc R 1 . .
    C C14 -0.05786(13) 0.07704(15) 0.78118(9) 0.0344(3) Uani d . 1 . .
    H H14 -0.1390 0.0294 0.7477 0.041 Uiso calc R 1 . .
    C C15 0.01500(13) 0.02096(15) 0.86617(9) 0.0341(3) Uani d . 1 . .
    H H15 -0.0165 -0.0650 0.8915 0.041 Uiso calc R 1 . .
    C C16 0.13418(12) 0.08994(14) 0.91473(8) 0.0281(3) Uani d . 1 . .
    H H16 0.1834 0.0508 0.9733 0.034 Uiso calc R 1 . .
    O O1 0.46398(10) 0.04232(10) 0.89213(6) 0.0388(2) Uani d . 1 . .
    O O2 0.37110(8) 0.22230(9) 1.01953(5) 0.02635(19) Uani d D 1 . .
    H H2O 0.4104(14) 0.1379(14) 1.0054(9) 0.040 Uiso d D 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0371(8) 0.0363(8) 0.0426(7) 0.0045(6) 0.0178(6) -0.0073(6)
    C2 0.0246(6) 0.0290(7) 0.0283(6) 0.0047(5) 0.0030(5) -0.0038(5)
    C3 0.0260(6) 0.0247(6) 0.0271(6) 0.0035(5) 0.0077(5) -0.0001(5)
    C4 0.0258(6) 0.0221(6) 0.0196(5) 0.0044(5) 0.0057(4) 0.0023(5)
    C5 0.0219(6) 0.0225(6) 0.0230(5) 0.0026(5) 0.0032(4) -0.0014(5)
    C6 0.0337(7) 0.0256(7) 0.0315(6) 0.0036(5) 0.0127(5) 0.0010(6)
    C7 0.0379(7) 0.0221(6) 0.0391(7) 0.0039(6) 0.0099(6) 0.0023(6)
    C8 0.0316(7) 0.0245(7) 0.0360(6) 0.0080(6) 0.0042(5) -0.0057(6)
    C9 0.0348(7) 0.0341(7) 0.0331(6) 0.0062(6) 0.0141(5) -0.0043(6)
    C10 0.0336(7) 0.0259(7) 0.0304(6) 0.0016(5) 0.0126(5) 0.0008(5)
    C11 0.0247(6) 0.0227(6) 0.0200(5) 0.0055(5) 0.0074(4) -0.0024(5)
    C12 0.0318(6) 0.0310(7) 0.0227(6) 0.0070(6) 0.0078(5) 0.0012(5)
    C13 0.0318(7) 0.0444(8) 0.0230(6) 0.0105(6) 0.0018(5) -0.0046(6)
    C14 0.0257(6) 0.0414(8) 0.0354(7) 0.0009(6) 0.0049(5) -0.0143(6)
    C15 0.0333(7) 0.0308(7) 0.0396(7) -0.0031(6) 0.0110(6) -0.0035(6)
    C16 0.0307(7) 0.0270(7) 0.0268(6) 0.0027(5) 0.0063(5) 0.0007(5)
    O1 0.0515(6) 0.0275(5) 0.0405(5) 0.0123(4) 0.0166(4) 0.0030(4)
    O2 0.0320(5) 0.0241(5) 0.0214(4) 0.0077(4) 0.0021(3) 0.0016(4)
_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_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.5009(16) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 O1 . 1.2165(15) ?
    C2 C3 . 1.5089(16) ?
    C3 C4 . 1.5403(15) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 O2 . 1.4266(13) ?
    C4 C5 . 1.5301(16) ?
    C4 C11 . 1.5373(16) ?
    C5 C6 . 1.3830(16) ?
    C5 C10 . 1.3964(15) ?
    C6 C7 . 1.3934(17) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3795(17) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.3828(18) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.3839(17) ?
    C9 H9 . 0.9500 ?
    C10 H10 . 0.9500 ?
    C11 C16 . 1.3866(16) ?
    C11 C12 . 1.3965(15) ?
    C12 C13 . 1.3855(17) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.3826(19) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.3808(18) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.3884(17) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    O2 H2O . 0.910(12) ?
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 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C1 . . 120.90(12) ?
    O1 C2 C3 . . 122.65(11) ?
    C1 C2 C3 . . 116.44(11) ?
    C2 C3 C4 . . 114.99(10) ?
    C2 C3 H3A . . 108.5 ?
    C4 C3 H3A . . 108.5 ?
    C2 C3 H3B . . 108.5 ?
    C4 C3 H3B . . 108.5 ?
    H3A C3 H3B . . 107.5 ?
    O2 C4 C5 . . 105.04(8) ?
    O2 C4 C11 . . 111.18(9) ?
    C5 C4 C11 . . 108.60(9) ?
    O2 C4 C3 . . 109.89(9) ?
    C5 C4 C3 . . 112.06(10) ?
    C11 C4 C3 . . 110.00(9) ?
    C6 C5 C10 . . 118.35(11) ?
    C6 C5 C4 . . 123.61(10) ?
    C10 C5 C4 . . 118.03(10) ?
    C5 C6 C7 . . 121.00(11) ?
    C5 C6 H6 . . 119.5 ?
    C7 C6 H6 . . 119.5 ?
    C8 C7 C6 . . 119.97(12) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C7 C8 C9 . . 119.65(12) ?
    C7 C8 H8 . . 120.2 ?
    C9 C8 H8 . . 120.2 ?
    C8 C9 C10 . . 120.33(11) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C9 C10 C5 . . 120.69(12) ?
    C9 C10 H10 . . 119.7 ?
    C5 C10 H10 . . 119.7 ?
    C16 C11 C12 . . 118.42(11) ?
    C16 C11 C4 . . 121.49(10) ?
    C12 C11 C4 . . 120.09(11) ?
    C13 C12 C11 . . 120.70(12) ?
    C13 C12 H12 . . 119.6 ?
    C11 C12 H12 . . 119.6 ?
    C14 C13 C12 . . 120.15(11) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 119.72(12) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C16 . . 120.17(12) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C11 C16 C15 . . 120.84(11) ?
    C11 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C4 O2 H2O . . 107.4(8) ?
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
    O1 C2 C3 C4 . . . . -15.52(17) ?
    C1 C2 C3 C4 . . . . 165.07(10) ?
    C2 C3 C4 O2 . . . . 57.09(13) ?
    C2 C3 C4 C5 . . . . 173.47(9) ?
    C2 C3 C4 C11 . . . . -65.63(12) ?
    O2 C4 C5 C6 . . . . 133.63(11) ?
    C11 C4 C5 C6 . . . . -107.35(12) ?
    C3 C4 C5 C6 . . . . 14.36(15) ?
    O2 C4 C5 C10 . . . . -47.29(13) ?
    C11 C4 C5 C10 . . . . 71.72(12) ?
    C3 C4 C5 C10 . . . . -166.56(10) ?
    C10 C5 C6 C7 . . . . -0.05(18) ?
    C4 C5 C6 C7 . . . . 179.02(11) ?
    C5 C6 C7 C8 . . . . 0.10(19) ?
    C6 C7 C8 C9 . . . . -0.17(19) ?
    C7 C8 C9 C10 . . . . 0.21(19) ?
    C8 C9 C10 C5 . . . . -0.16(19) ?
    C6 C5 C10 C9 . . . . 0.08(18) ?
    C4 C5 C10 C9 . . . . -179.04(11) ?
    O2 C4 C11 C16 . . . . -2.22(14) ?
    C5 C4 C11 C16 . . . . -117.30(11) ?
    C3 C4 C11 C16 . . . . 119.73(11) ?
    O2 C4 C11 C12 . . . . 177.02(10) ?
    C5 C4 C11 C12 . . . . 61.94(13) ?
    C3 C4 C11 C12 . . . . -61.03(13) ?
    C16 C11 C12 C13 . . . . -0.53(17) ?
    C4 C11 C12 C13 . . . . -179.79(11) ?
    C11 C12 C13 C14 . . . . -0.24(18) ?
    C12 C13 C14 C15 . . . . 0.74(18) ?
    C13 C14 C15 C16 . . . . -0.48(19) ?
    C12 C11 C16 C15 . . . . 0.79(17) ?
    C4 C11 C16 C15 . . . . -179.96(11) ?
    C14 C15 C16 C11 . . . . -0.29(18) ?
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
    O2 H2O O1 . 0.910(12) 2.016(12) 2.7636(12) 138.5(11)
    O2 H2O O1 3_657 0.910(12) 2.385(13) 3.0530(12) 130.3(10)
data_global
_journal_date_recd_electronic     2008-07-03
_journal_date_accepted     2008-07-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1465
_journal_page_last     o1465
_journal_paper_category     QO
_journal_coeditor_code     HG2422
_publ_contact_author_name     'John McMurtrie'
_publ_contact_author_address
;
School of Physical and Chemical Sciences
Queensland University of Technology
2 George St
Brisbane, Queensland, 4001,
Australia.
;
_publ_contact_author_email     j.mcmurtrie@qut.edu.au
_publ_contact_author_fax      61731381804
_publ_contact_author_phone      61731381220
_publ_section_title
;
4-Hydroxy-4,4-diphenylbutan-2-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Arnold, Dennis P.'
;
;
;
School of Physical and Chemical Sciences
Queensland University of Technology
2 George St
Brisbane, Queensland 4001,
Australia
;
    'McMurtrie, John C.'
;
;
;
School of Physical and Chemical Sciences
Queensland University of Technology
2 George St
Brisbane, Queensland 4001,
Australia
;
