##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2005-05-20
_journal_date_accepted     2005-08-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     o3011
_journal_page_last     o3013
_journal_paper_category     EO
_journal_coeditor_code     ER6020
_publ_contact_author_name     'Arvid Mostad'
_publ_contact_author_address
;
Department of Chemistry
University of Oslo
P.O. Box 1033 Blindern
N-0315 Oslo, Norway
;
_publ_contact_author_email     arvidm@kjemi.uio.no
_publ_contact_author_fax     '+47 22 85 54 41'
_publ_contact_author_phone     '+47 22 85 54 15'
_publ_section_title
;
Weak hydrogen bonds in 5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Arrieta, Antonio F. '
; ?
;
;
Leibniz-Institut für Organische Katalyse
Albert-Einstein-Straße 29a
D-18059 Rostock
Germany
;
    'Arvid Mostad. '
; ?
;
;
Department of Chemistry
University of Oslo
PO Box 1033 Blindern
N-0315 Oslo
Norway
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 O3'
_chemical_formula_sum     'C18 H16 O3'
_chemical_formula_iupac     'C18 H16 O3'
_chemical_formula_weight     280.31
_chemical_melting_point        .393E-305
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     3.9754(8)
_cell_length_b     9.790(2)
_cell_length_c     17.958(4)
_cell_angle_alpha     90.00
_cell_angle_beta     92.91(3)
_cell_angle_gamma     90.00
_cell_volume     698.0(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     10099
_cell_measurement_theta_min     2.07
_cell_measurement_theta_max     28.38
_cell_measurement_temperature     105(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2002)'
_exptl_absorpt_correction_T_min     0.9646
_exptl_absorpt_correction_T_max     0.9910
_exptl_special_details
;
;
_diffrn_ambient_temperature     105(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'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8
_diffrn_reflns_number     11132
_diffrn_reflns_av_R_equivalents     0.0220
_diffrn_reflns_av_sigmaI/netI     0.0129
_diffrn_reflns_theta_min     1.14
_diffrn_reflns_theta_max     28.30
_diffrn_reflns_theta_full     28.30
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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     1838
_reflns_number_gt     1794
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0292
_refine_ls_R_factor_gt     0.0284
_refine_ls_wR_factor_gt     0.0766
_refine_ls_wR_factor_ref     0.0793
_refine_ls_goodness_of_fit_ref     1.120
_refine_ls_restrained_S_all     1.120
_refine_ls_number_reflns     1838
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0881P)²+0.4691P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.020
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.238
_refine_diff_density_min     -0.214
_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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_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
    O1 0.7478(3) 0.23595(12) 0.28853(6) 0.0277(3) Uani d . 1 . . O
    O2 0.6016(3) 0.29013(12) 0.15712(6) 0.0309(3) Uani d . 1 . . O
    O3 0.8910(3) 0.37033(14) 0.75071(6) 0.0271(2) Uani d . 1 . . O
    C1 0.4700(4) 0.40322(15) 0.17643(8) 0.0220(3) Uani d . 1 . . C
    C2 0.4670(4) 0.43937(16) 0.25299(8) 0.0216(3) Uani d . 1 . . C
    H2 0.361(5) 0.522(3) 0.2661(12) 0.028(5) Uiso d . 1 . . H
    C3 0.6085(4) 0.35162(16) 0.30711(8) 0.0215(3) Uani d . 1 . . C
    C4 0.6079(4) 0.38521(17) 0.38649(8) 0.0221(3) Uani d . 1 . . C
    H4 0.488(6) 0.467(3) 0.3969(12) 0.032(5) Uiso d . 1 . . H
    C5 0.7587(4) 0.30436(15) 0.43892(8) 0.0213(3) Uani d . 1 . . C
    H5 0.858(5) 0.223(2) 0.4223(10) 0.020(4) Uiso d . 1 . . H
    C6 0.7792(3) 0.32671(15) 0.51963(8) 0.0199(3) Uani d . 1 . . C
    C7 0.9452(4) 0.22908(16) 0.56558(9) 0.0228(3) Uani d . 1 . . C
    H7 1.034(5) 0.154(3) 0.5430(11) 0.030(5) Uiso d . 1 . . H
    C8 0.9768(4) 0.24602(17) 0.64229(8) 0.0234(3) Uani d . 1 . . C
    H8 1.090(5) 0.182(3) 0.6734(12) 0.033(5) Uiso d . 1 . . H
    C9 0.8427(3) 0.36190(16) 0.67501(8) 0.0215(3) Uani d . 1 . . C
    C10 0.6743(4) 0.46067(16) 0.63072(8) 0.0220(3) Uani d . 1 . . C
    H10 0.580(5) 0.543(3) 0.6536(12) 0.032(5) Uiso d . 1 . . H
    C11 0.6444(4) 0.44191(15) 0.55375(8) 0.0213(3) Uani d . 1 . . C
    H11 0.525(6) 0.516(3) 0.5259(11) 0.034(6) Uiso d . 1 . . H
    C12 0.7318(4) 0.4814(2) 0.78748(8) 0.0283(3) Uani d . 1 . . C
    H122 0.784(6) 0.465(3) 0.8432(12) 0.041(6) Uiso d . 1 . . H
    H123 0.496(6) 0.479(3) 0.7785(11) 0.031(5) Uiso d . 1 . . H
    H121 0.807(6) 0.567(3) 0.7704(12) 0.035(6) Uiso d . 1 . . H
    C13 0.3293(3) 0.49390(15) 0.11628(8) 0.0201(3) Uani d . 1 . . C
    C14 0.1465(4) 0.61172(16) 0.13135(8) 0.0233(3) Uani d . 1 . . C
    H14 0.103(5) 0.638(2) 0.1817(12) 0.026(5) Uiso d . 1 . . H
    C15 0.0218(4) 0.69481(16) 0.07341(9) 0.0260(3) Uani d . 1 . . C
    C16 0.0827(4) 0.66171(17) -0.00027(9) 0.0251(3) Uani d . 1 . . C
    H16 -0.007(6) 0.720(3) -0.0395(12) 0.037(6) Uiso d . 1 . . H
    H15 -0.112(5) 0.773(3) 0.0841(12) 0.035(6) Uiso d . 1 . . H
    C17 0.2669(4) 0.54523(17) -0.01551(8) 0.0245(3) Uani d . 1 . . C
    H17 0.315(5) 0.525(2) -0.0671(11) 0.032(5) Uiso d . 1 . . H
    C18 0.3876(4) 0.46115(16) 0.04206(8) 0.0227(3) Uani d . 1 . . C
    H18 0.519(5) 0.382(2) 0.0312(11) 0.027(5) Uiso d . 1 . . H
    H21 0.708(10) 0.243(5) 0.222(2) 0.110(14) Uiso d . 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
    O1 C3 . 1.3110(19) y
    O1 H21 . 1.19(4) n
    O2 C1 . 1.2797(19) y
    O2 H21 . 1.31(4) n
    O3 C9 . 1.3657(17) y
    O3 C12 . 1.436(2) y
    C1 C2 . 1.4203(19) y
    C1 C13 . 1.485(2) y
    C2 C3 . 1.394(2) y
    C2 H2 . 0.94(2) n
    C3 C4 . 1.4631(19) y
    C4 C5 . 1.347(2) y
    C4 H4 . 0.96(3) n
    C5 C6 . 1.4638(19) y
    C5 H5 . 0.94(2) n
    C6 C11 . 1.403(2) n
    C6 C7 . 1.405(2) n
    C7 C8 . 1.387(2) n
    C7 H7 . 0.92(3) n
    C8 C9 . 1.396(2) n
    C8 H8 . 0.94(2) n
    C9 C10 . 1.401(2) n
    C10 C11 . 1.393(2) n
    C10 H10 . 0.99(2) n
    C11 H11 . 0.99(2) n
    C12 H122 . 1.02(2) n
    C12 H123 . 0.94(2) n
    C12 H121 . 0.95(3) n
    C13 C14 . 1.397(2) n
    C13 C18 . 1.4014(19) n
    C14 C15 . 1.392(2) n
    C14 H14 . 0.97(2) n
    C15 C16 . 1.395(2) n
    C15 H15 . 0.95(2) n
    C16 C17 . 1.390(2) n
    C16 H16 . 0.96(2) n
    C17 C18 . 1.388(2) n
    C17 H17 . 0.97(2) n
    C18 H18 . 0.96(2) n
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
    C3 O1 H21 . . 100(2) n
    C1 O2 H21 . . 100(2) n
    C9 O3 C12 . . 117.43(12) y
    O2 C1 C2 . . 120.09(14) y
    O2 C1 C13 . . 117.65(12) y
    C2 C1 C13 . . 122.25(13) y
    C3 C2 C1 . . 119.89(14) y
    C3 C2 H2 . . 121.4(13) n
    C1 C2 H2 . . 118.7(13) n
    O1 C3 C2 . . 121.03(13) y
    O1 C3 C4 . . 117.63(13) y
    C2 C3 C4 . . 121.34(14) y
    C5 C4 C3 . . 121.74(14) y
    C5 C4 H4 . . 124.4(13) n
    C3 C4 H4 . . 113.9(13) n
    C4 C5 C6 . . 127.19(14) y
    C4 C5 H5 . . 117.0(11) n
    C6 C5 H5 . . 115.8(11) n
    C11 C6 C7 . . 117.95(13) n
    C11 C6 C5 . . 123.32(13) y
    C7 C6 C5 . . 118.72(13) y
    C8 C7 C6 . . 121.21(14) n
    C8 C7 H7 . . 121.2(13) n
    C6 C7 H7 . . 117.6(13) n
    C7 C8 C9 . . 119.87(13) n
    C7 C8 H8 . . 121.8(14) n
    C9 C8 H8 . . 118.4(14) n
    O3 C9 C8 . . 115.52(13) n
    O3 C9 C10 . . 124.23(14) n
    C8 C9 C10 . . 120.25(13) n
    C11 C10 C9 . . 119.12(13) n
    C11 C10 H10 . . 120.4(12) n
    C9 C10 H10 . . 120.5(12) n
    C10 C11 C6 . . 121.60(13) n
    C10 C11 H11 . . 115.0(13) n
    C6 C11 H11 . . 123.4(12) n
    O3 C12 H122 . . 104.8(15) n
    O3 C12 H123 . . 111.2(15) n
    H122 C12 H123 . . 108.2(18) n
    O3 C12 H121 . . 111.6(14) n
    H122 C12 H121 . . 114(2) n
    H123 C12 H121 . . 107(2) n
    C14 C13 C18 . . 119.07(13) n
    C14 C13 C1 . . 122.21(13) y
    C18 C13 C1 . . 118.71(13) y
    C15 C14 C13 . . 120.44(14) n
    C15 C14 H14 . . 117.9(13) n
    C13 C14 H14 . . 121.7(13) n
    C14 C15 C16 . . 120.06(14) n
    C14 C15 H15 . . 119.8(13) n
    C16 C15 H15 . . 120.1(13) n
    C17 C16 C15 . . 119.72(14) n
    C17 C16 H16 . . 121.4(14) n
    C15 C16 H16 . . 118.9(14) n
    C18 C17 C16 . . 120.37(14) n
    C18 C17 H17 . . 120.8(14) n
    C16 C17 H17 . . 118.8(14) n
    C17 C18 C13 . . 120.33(14) n
    C17 C18 H18 . . 119.9(12) n
    C13 C18 H18 . . 119.7(12) n
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
    O2 C1 C2 C3 . . . . 0.2(2) y
    C13 C1 C2 C3 . . . . -178.74(13) y
    C1 C2 C3 O1 . . . . 0.5(2) y
    C1 C2 C3 C4 . . . . -179.61(13) y
    O1 C3 C4 C5 . . . . 3.2(2) y
    C2 C3 C4 C5 . . . . -176.65(14) y
    C3 C4 C5 C6 . . . . 179.36(14) y
    C4 C5 C6 C11 . . . . -1.5(2) y
    C4 C5 C6 C7 . . . . 179.25(14) y
    C11 C6 C7 C8 . . . . -0.3(2) n
    C5 C6 C7 C8 . . . . 178.98(14) n
    C6 C7 C8 C9 . . . . -0.1(2) n
    C12 O3 C9 C8 . . . . -174.56(13) y
    C12 O3 C9 C10 . . . . 6.0(2) y
    C7 C8 C9 O3 . . . . -179.07(13) y
    C7 C8 C9 C10 . . . . 0.4(2) n
    O3 C9 C10 C11 . . . . 179.12(13) y
    C8 C9 C10 C11 . . . . -0.3(2) n
    C9 C10 C11 C6 . . . . -0.1(2) n
    C7 C6 C11 C10 . . . . 0.4(2) n
    C5 C6 C11 C10 . . . . -178.84(13) n
    O2 C1 C13 C14 . . . . 172.53(14) y
    C2 C1 C13 C14 . . . . -8.5(2) y
    O2 C1 C13 C18 . . . . -8.7(2) y
    C2 C1 C13 C18 . . . . 170.29(13) y
    C18 C13 C14 C15 . . . . 0.5(2) n
    C1 C13 C14 C15 . . . . 179.31(14) n
    C13 C14 C15 C16 . . . . -0.8(2) n
    C14 C15 C16 C17 . . . . 0.3(2) n
    C15 C16 C17 C18 . . . . 0.6(2) n
    C16 C17 C18 C13 . . . . -0.9(2) n
    C14 C13 C18 C17 . . . . 0.4(2) n
    C1 C13 C18 C17 . . . . -178.47(13) n
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
    C18 H18 C16 2_645 0.96(2) 2.75(2) 3.708(2) 178(2)
    C12 H121 O1 2_756 0.95(3) 2.68(2) 3.556(2) 154(2)
    C12 H123 O3 1_455 0.94(2) 2.65(2) 3.545(2) 158(2)
    C10 H10 O1 2_656 0.99(2) 2.55(2) 3.525(2) 172(2)
    C14 H14 O3 2_656 0.97(2) 2.57(2) 3.3089(19) 133(2)
    O1 H21 O2 . 1.19(4) 1.31(4) 2.4594(16) 159(4)
