##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_k52_01
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.2
_journal_date_recd_electronic     2002-01-18
_journal_date_accepted     2002-01-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue      3
_journal_page_first     o298
_journal_page_last     o299
_journal_paper_category     EO
_publ_contact_author_name     'Gary D. Fallon'
_publ_contact_author_address
;
School of Chemistry
PO Box 23
Monash University
Victoria 3800
Australia
;
_publ_contact_author_email     'g.fallon@sci.monash.edu.au'
_publ_contact_author_fax     '613 9905 4597'
_publ_contact_author_phone     '613 9905 4588'
_publ_section_title
;
(+-)-2-Oxo-4-(2-oxo-2-phenylethyl)-5-phenyltetrahydrofuran-3-carboxylic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Greatrex, Ben W.'
;
Department of Chemistry
University of Adelaide
South Australia 5005
Australia
;
    'Kimber, Marc C.'
;
Department of Chemistry
University of Adelaide
South Australia 5005
Australia
;
    'Taylor, Dennis K.'
;
Department of Chemistry
University of Adelaide
South Australia 5005
Australia
;
    'Fallon, Gary D.'
;
School of Chemistry
PO Box 23
Monash University
Victoria 3800
Australia
;
data_I
_chemical_formula_moiety     'C19 H16 O5'
_chemical_formula_sum     'C19 H16 O5'
_chemical_formula_iupac     'C19 H16 O5'
_chemical_formula_weight     324.32
_chemical_melting_point     '130-132'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     30.0282(4)
_cell_length_b     8.92260(10)
_cell_length_c     12.1979(2)
_cell_angle_alpha     90
_cell_angle_beta     104.8840(10)
_cell_angle_gamma     90
_cell_volume     3158.52(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     20303
_cell_measurement_theta_min     3.4
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     123(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .27
_exptl_crystal_size_mid      .13
_exptl_crystal_size_min      .1
_exptl_crystal_density_diffrn     1.364
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1360
_exptl_absorpt_coefficient_mu      .099
_exptl_absorpt_correction_type     none
_exptl_special_details
;
m.p. 130-132°C decomp.
IR(nujol) 1783, 1711, 1678, 1457, 1377, 1336, 1300, 1267 cm⁻¹.
¹H n.m.r. (300MHz, CDCl₃): δ 2.67 (dd,J=9.3, 18.6 Hz, 1H),
3.26 (dd,J=5.1, 18.6 Hz, 1H),
3.64 (d,J=10.8 Hz, 1H),
3.90, (dddd,J=5.1, 7.8, 9.3, 10.8 Hz, 1H),
6.14 (d,J=7.8 Hz, 1H),
7.12-7.14 (m,2H),
7.31-7.36 (m,3H),
7.42-7.44 (m,2H),
7.51-7.57 (m,1H),
7.74-7.77 (m,2H).
MS (M⁺,%) 324
(M^.+^, 12), 280(10), 252(18), 174(15), 146(28), 120(25),
105(100), 77(52).
Anal. Calcd. for C₁₉H₁₆O₅: C, 70.36; H, 4.97%.
Found C, 70.31; H, 4.90%.
;
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'CCD-rotation images, thick slices'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21591
_diffrn_reflns_av_R_equivalents      .037
_diffrn_reflns_theta_min     3.4
_diffrn_reflns_theta_max     28.3
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max      .989
_diffrn_measured_fraction_theta_full      .996
_diffrn_reflns_limit_h_min     -40
_diffrn_reflns_limit_h_max     40
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_reflns_number_total     3871
_reflns_number_gt     3023
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt      .045
_refine_ls_wR_factor_ref      .096
_refine_ls_goodness_of_fit_ref     1.03
_refine_ls_restrained_S_all     1.03
_refine_ls_number_reflns     3871
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
      'calc w = 1/[σ²(Fo²)+(0.033P)²+2.4814P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_diff_density_max      .25
_refine_diff_density_min      -.21
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C  .0033  .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O  .0106  .006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius BV, 1997-2000)'
_computing_cell_refinement     'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    O2  .02622(3)  .06044(11)  .61898(8)  .0237(2) Uani d . 1 . . O
    O3  .05222(3)  .43059(11)  .51859(9)  .0310(3) Uani d . 1 . . O
    O1  .09404(3)  -.00993(10)  .59291(7)  .0211(2) Uani d . 1 . . O
    O5  .19441(3)  .20465(11)  .45237(8)  .0264(2) Uani d . 1 . . O
    O4  -.01351(3)  .31388(11)  .43670(10)  .0364(3) Uani d . 1 . . O
    H4  -.0251  .3952  .4503  .055 Uiso calc R 1 . . H
    C6'  .18191(4)  .32455(14)  .27511(11)  .0192(3) Uani d . 1 . . C
    C7  .12161(5)  -.09861(15)  .43314(11)  .0223(3) Uani d . 1 . . C
    C8'  .16888(5)  .42504(16)  .08592(12)  .0259(3) Uani d . 1 . . C
    H8'  .1496  .4375  .0115  .031 Uiso calc R 1 . . H
    C2  .05491(5)  .07121(14)  .56675(11)  .0196(3) Uani d . 1 . . C
    C3  .05476(4)  .17228(14)  .46548(11)  .0185(3) Uani d . 1 . . C
    H3  .0377  .121  .3941  .022 Uiso calc R 1 . . H
    C6  .03137(4)  .31961(15)  .47628(11)  .0204(3) Uani d . 1 . . C
    C4  .10582(4)  .18119(14)  .46827(11)  .0184(3) Uani d . 1 . . C
    H4a  .1202  .2594  .5251  .022 Uiso calc R 1 . . H
    C5'  .16628(5)  .24622(14)  .36648(11)  .0197(3) Uani d . 1 . . C
    C5  .12375(5)  .02611(15)  .51819(11)  .0203(3) Uani d . 1 . . C
    H5  .1562  .037  .565  .024 Uiso calc R 1 . . H
    C12  .08136(5)  -.17789(16)  .38821(11)  .0257(3) Uani d . 1 . . C
    H12  .0544  -.1559  .4123  .031 Uiso calc R 1 . . H
    C4'  .11532(4)  .22346(15)  .35525(11)  .0192(3) Uani d . 1 . . C
    H4'1  .1036  .1432  .2992  .023 Uiso calc R 1 . . H
    H4'2  .0985  .3169  .3267  .023 Uiso calc R 1 . . H
    C10  .11918(7)  -.32168(18)  .27205(13)  .0385(4) Uani d . 1 . . C
    H10  .1182  -.397  .2164  .046 Uiso calc R 1 . . H
    C11'  .22634(5)  .38428(16)  .30194(12)  .0237(3) Uani d . 1 . . C
    H11'  .2463  .3683  .3752  .028 Uiso calc R 1 . . H
    C8  .16096(6)  -.13375(17)  .39779(14)  .0318(4) Uani d . 1 . . C
    H8  .1889  -.0817  .4292  .038 Uiso calc R 1 . . H
    C9'  .21256(5)  .48722(17)  .11422(12)  .0289(3) Uani d . 1 . . C
    H9'  .2229  .5441  .0597  .035 Uiso calc R 1 . . H
    C7'  .15318(5)  .34436(15)  .16621(11)  .0219(3) Uani d . 1 . . C
    H7'  .123  .3029  .147  .026 Uiso calc R 1 . . H
    C9  .15950(6)  -.24448(18)  .31686(14)  .0398(4) Uani d . 1 . . C
    H9  .1863  -.267  .2924  .048 Uiso calc R 1 . . H
    C10'  .24141(5)  .46674(17)  .22220(12)  .0282(3) Uani d . 1 . . C
    H10'  .2714  .5092  .2413  .034 Uiso calc R 1 . . H
    C11  .08033(6)  -.28965(17)  .30798(13)  .0339(4) Uani d . 1 . . C
    H11  .0527  -.3441  .2779  .041 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
    O2 C2 . 1.1996(16) ?
    O3 C6 . 1.2137(16) ?
    O1 C2 . 1.3470(16) ?
    O1 C5 . 1.4653(15) ?
    O5 C5' . 1.2224(16) ?
    O4 C6 . 1.3106(16) ?
    O4 H4 .  .84 ?
    C6' C11' . 1.3953(19) ?
    C6' C7' . 1.3970(18) ?
    C6' C5' . 1.4900(18) ?
    C7 C12 . 1.386(2) ?
    C7 C8 . 1.3934(19) ?
    C7 C5 . 1.5115(19) ?
    C8' C9' . 1.384(2) ?
    C8' C7' . 1.3917(19) ?
    C8' H8' .  .95 ?
    C2 C3 . 1.5285(18) ?
    C3 C6 . 1.5120(18) ?
    C3 C4 . 1.5269(17) ?
    C3 H3 . 1 ?
    C4 C4' . 1.5252(18) ?
    C4 C5 . 1.5514(18) ?
    C4 H4a . 1 ?
    C5' C4' . 1.5143(18) ?
    C5 H5 . 1 ?
    C12 C11 . 1.392(2) ?
    C12 H12 .  .95 ?
    C4' H4'1 .  .99 ?
    C4' H4'2 .  .99 ?
    C10 C11 . 1.377(2) ?
    C10 C9 . 1.378(3) ?
    C10 H10 .  .95 ?
    C11' C10' . 1.3850(19) ?
    C11' H11' .  .95 ?
    C8 C9 . 1.389(2) ?
    C8 H8 .  .95 ?
    C9' C10' . 1.390(2) ?
    C9' H9' .  .95 ?
    C7' H7' .  .95 ?
    C9 H9 .  .95 ?
    C10' H10' .  .95 ?
    C11 H11 .  .95 ?
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 O1 C5 . . 111.60(10) ?
    C6 O4 H4 . . 109.5 ?
    C11' C6' C7' . . 119.64(12) ?
    C11' C6' C5' . . 118.02(12) ?
    C7' C6' C5' . . 122.30(12) ?
    C12 C7 C8 . . 119.04(13) ?
    C12 C7 C5 . . 121.73(12) ?
    C8 C7 C5 . . 119.23(13) ?
    C9' C8' C7' . . 120.17(13) ?
    C9' C8' H8' . . 119.9 ?
    C7' C8' H8' . . 119.9 ?
    O2 C2 O1 . . 122.21(12) ?
    O2 C2 C3 . . 128.53(12) ?
    O1 C2 C3 . . 109.26(10) ?
    C6 C3 C4 . . 116.04(11) ?
    C6 C3 C2 . . 110.34(10) ?
    C4 C3 C2 . . 102.61(10) ?
    C6 C3 H3 . . 109.2 ?
    C4 C3 H3 . . 109.2 ?
    C2 C3 H3 . . 109.2 ?
    O3 C6 O4 . . 123.91(12) ?
    O3 C6 C3 . . 123.09(12) ?
    O4 C6 C3 . . 113.00(11) ?
    C4' C4 C3 . . 114.38(11) ?
    C4' C4 C5 . . 116.66(10) ?
    C3 C4 C5 . . 101.98(10) ?
    C4' C4 H4a . . 107.8 ?
    C3 C4 H4a . . 107.8 ?
    C5 C4 H4a . . 107.8 ?
    O5 C5' C6' . . 120.15(12) ?
    O5 C5' C4' . . 119.78(12) ?
    C6' C5' C4' . . 120.03(11) ?
    O1 C5 C7 . . 109.89(11) ?
    O1 C5 C4 . . 103.57(10) ?
    C7 C5 C4 . . 115.97(11) ?
    O1 C5 H5 . . 109.1 ?
    C7 C5 H5 . . 109.1 ?
    C4 C5 H5 . . 109.1 ?
    C7 C12 C11 . . 120.20(14) ?
    C7 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C5' C4' C4 . . 111.76(10) ?
    C5' C4' H4'1 . . 109.3 ?
    C4 C4' H4'1 . . 109.3 ?
    C5' C4' H4'2 . . 109.3 ?
    C4 C4' H4'2 . . 109.3 ?
    H4'1 C4' H4'2 . . 107.9 ?
    C11 C10 C9 . . 119.97(15) ?
    C11 C10 H10 . . 120 ?
    C9 C10 H10 . . 120 ?
    C10' C11' C6' . . 120.22(13) ?
    C10' C11' H11' . . 119.9 ?
    C6' C11' H11' . . 119.9 ?
    C9 C8 C7 . . 120.36(16) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8' C9' C10' . . 120.25(13) ?
    C8' C9' H9' . . 119.9 ?
    C10' C9' H9' . . 119.9 ?
    C8' C7' C6' . . 119.77(13) ?
    C8' C7' H7' . . 120.1 ?
    C6' C7' H7' . . 120.1 ?
    C10 C9 C8 . . 120.09(15) ?
    C10 C9 H9 . . 120 ?
    C8 C9 H9 . . 120 ?
    C11' C10' C9' . . 119.91(13) ?
    C11' C10' H10' . . 120 ?
    C9' C10' H10' . . 120 ?
    C10 C11 C12 . . 120.32(16) ?
    C10 C11 H11 . . 119.8 ?
    C12 C11 H11 . . 119.8 ?
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 O3 5_566  .84 1.84 2.6782(14) 178
