##############################################################################
###                                                                        ###
###        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                #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2006-11-22
_journal_date_accepted     2006-11-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      1
_journal_page_first     o54
_journal_page_last     o56
_journal_paper_category     EO
_journal_coeditor_code     SJ2180
_publ_contact_author_name     'Prof. Fun Hoong Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6577888  Ext. 3690'
_publ_section_title
;
1-(4-Fluorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Jeannie Bee-Jan Teh' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'P. S. Patil' ?
;    Department of Studies in Physics
     Mangalore University
     Mangalagangotri
     Mangalore 574 199
     India
;
    'Hoong-Kun Fun' ?
;    X-ray Crystallography Unit
     School of Physics
     Universiti Sains Malaysia
     11800 USM, Penang
     Malaysia
;
    'Ibrahim Abdul Razak' ?
;    X-ray Crystallography Unit
     School of Physics
     Universiti Sains Malaysia
     11800 USM, Penang
     Malaysia
;
    'S. M. Dharmaprakash' ?
;    Department of Studies in Physics
     Mangalore University
     Mangalagangotri
     Mangalore 574 199
     India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(4-Fluorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 F O4'
_chemical_formula_sum     'C18 H17 F O4'
_chemical_formula_iupac     'C18 H17 F O4'
_chemical_formula_weight     316.32
_chemical_melting_point     ?
_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     8.5325(2)
_cell_length_b     8.8404(2)
_cell_length_c     10.1468(2)
_cell_angle_alpha     87.0480(10)
_cell_angle_beta     73.3130(10)
_cell_angle_gamma     85.9190(10)
_cell_volume     730.90(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6193
_cell_measurement_theta_min     2.10
_cell_measurement_theta_max     32.50
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     Block
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.52
_exptl_crystal_size_min     0.51
_exptl_crystal_density_diffrn     1.437
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     332
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9350
_exptl_absorpt_correction_T_max     0.9459
_exptl_special_details
;
;
_diffrn_ambient_temperature     297(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 APEX2 CCD
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     18180
_diffrn_reflns_av_R_equivalents     0.0214
_diffrn_reflns_av_sigmaI/netI     0.0193
_diffrn_reflns_theta_min     2.10
_diffrn_reflns_theta_max     32.50
_diffrn_reflns_theta_full     32.50
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     5266
_reflns_number_gt     4726
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0443
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.1185
_refine_ls_wR_factor_ref     0.1229
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     5266
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0739P)²+0.1553P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.550
_refine_diff_density_min     -0.303
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'APEX2'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
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
    F F1 0.91205(7) 0.27494(8) 0.52013(7) 0.03012(15) Uani d . 1 . .
    O O1 0.29214(8) 0.39667(7) 0.30815(7) 0.02026(13) Uani d . 1 . .
    O O2 0.04143(7) 0.68679(7) 0.02825(7) 0.01908(13) Uani d . 1 . .
    O O3 0.29784(7) 1.08381(7) -0.29340(6) 0.01864(13) Uani d . 1 . .
    O O4 0.57204(7) 1.01833(7) -0.23947(6) 0.01902(13) Uani d . 1 . .
    C C1 0.69568(10) 0.50196(9) 0.31411(8) 0.01706(14) Uani d . 1 . .
    H H1A 0.7078 0.5897 0.2584 0.020 Uiso calc R 1 . .
    C C2 0.81770(10) 0.45281(10) 0.37523(9) 0.01934(15) Uani d . 1 . .
    H H2A 0.9122 0.5055 0.3600 0.023 Uiso calc R 1 . .
    C C3 0.79425(10) 0.32319(10) 0.45934(9) 0.01956(16) Uani d . 1 . .
    C C4 0.65617(11) 0.24121(10) 0.48521(8) 0.01937(15) Uani d . 1 . .
    H H4A 0.6432 0.1556 0.5437 0.023 Uiso calc R 1 . .
    C C5 0.53743(10) 0.29054(9) 0.42124(8) 0.01659(14) Uani d . 1 . .
    H H5A 0.4445 0.2358 0.4357 0.020 Uiso calc R 1 . .
    C C6 0.55467(9) 0.42088(8) 0.33543(7) 0.01401(13) Uani d . 1 . .
    C C7 0.41811(10) 0.46668(9) 0.27395(8) 0.01475(14) Uani d . 1 . .
    C C8 0.43671(10) 0.59369(9) 0.17135(8) 0.01640(14) Uani d . 1 . .
    H H8A 0.5300 0.6490 0.1488 0.020 Uiso calc R 1 . .
    C C9 0.31695(9) 0.62835(9) 0.11098(8) 0.01476(14) Uani d . 1 . .
    H H9A 0.2247 0.5719 0.1416 0.018 Uiso calc R 1 . .
    C C10 0.31405(9) 0.74315(8) 0.00374(8) 0.01387(13) Uani d . 1 . .
    C C11 0.16957(9) 0.77412(9) -0.03503(8) 0.01415(13) Uani d . 1 . .
    C C12 0.15849(9) 0.88987(9) -0.13193(8) 0.01476(14) Uani d . 1 . .
    H H12A 0.0601 0.9123 -0.1531 0.018 Uiso calc R 1 . .
    C C13 0.29475(9) 0.97125(9) -0.19648(8) 0.01413(14) Uani d . 1 . .
    C C14 0.44441(9) 0.93665(9) -0.16461(8) 0.01427(14) Uani d . 1 . .
    C C15 0.45130(9) 0.82633(9) -0.06458(8) 0.01460(14) Uani d . 1 . .
    H H15A 0.5489 0.8063 -0.0416 0.018 Uiso calc R 1 . .
    C C16 -0.09566(10) 0.69496(9) -0.02582(9) 0.01811(15) Uani d . 1 . .
    H H16A -0.1648 0.6135 0.0136 0.027 Uiso calc R 1 . .
    H H16B -0.0580 0.6866 -0.1240 0.027 Uiso calc R 1 . .
    H H16C -0.1566 0.7903 -0.0035 0.027 Uiso calc R 1 . .
    C C17 0.15215(10) 1.11696(10) -0.33490(9) 0.01898(15) Uani d . 1 . .
    H H17A 0.1717 1.1943 -0.4067 0.028 Uiso calc R 1 . .
    H H17B 0.0649 1.1520 -0.2576 0.028 Uiso calc R 1 . .
    H H17C 0.1220 1.0269 -0.3682 0.028 Uiso calc R 1 . .
    C C18 0.73204(10) 0.96730(10) -0.23273(9) 0.01910(15) Uani d . 1 . .
    H H18A 0.8122 1.0245 -0.2985 0.029 Uiso calc R 1 . .
    H H18B 0.7511 0.8616 -0.2532 0.029 Uiso calc R 1 . .
    H H18C 0.7405 0.9815 -0.1419 0.029 Uiso calc R 1 . .
_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
    F1 C3 . 1.3567(9) ?
    O1 C7 . 1.2317(10) ?
    O2 C11 . 1.3673(9) ?
    O2 C16 . 1.4237(10) ?
    O3 C13 . 1.3586(9) ?
    O3 C17 . 1.4299(9) ?
    O4 C14 . 1.3656(9) ?
    O4 C18 . 1.4264(10) ?
    C1 C2 . 1.3915(11) ?
    C1 C6 . 1.4020(11) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.3839(12) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.3808(13) ?
    C4 C5 . 1.3869(11) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.3981(10) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.4950(11) ?
    C7 C8 . 1.4764(11) ?
    C8 C9 . 1.3449(10) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.4535(10) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.4032(10) ?
    C10 C15 . 1.4130(10) ?
    C11 C12 . 1.3996(10) ?
    C12 C13 . 1.3898(10) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.4142(10) ?
    C14 C15 . 1.3817(10) ?
    C15 H15A . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
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
    C11 O2 C16 . . 117.88(6) ?
    C13 O3 C17 . . 117.50(6) ?
    C14 O4 C18 . . 117.12(6) ?
    C2 C1 C6 . . 120.85(7) ?
    C2 C1 H1A . . 119.6 ?
    C6 C1 H1A . . 119.6 ?
    C3 C2 C1 . . 118.00(8) ?
    C3 C2 H2A . . 121.0 ?
    C1 C2 H2A . . 121.0 ?
    F1 C3 C4 . . 118.40(7) ?
    F1 C3 C2 . . 118.43(8) ?
    C4 C3 C2 . . 123.17(7) ?
    C3 C4 C5 . . 117.90(7) ?
    C3 C4 H4A . . 121.0 ?
    C5 C4 H4A . . 121.0 ?
    C4 C5 C6 . . 121.32(7) ?
    C4 C5 H5A . . 119.3 ?
    C6 C5 H5A . . 119.3 ?
    C5 C6 C1 . . 118.74(7) ?
    C5 C6 C7 . . 117.24(7) ?
    C1 C6 C7 . . 124.01(7) ?
    O1 C7 C8 . . 120.73(7) ?
    O1 C7 C6 . . 119.59(7) ?
    C8 C7 C6 . . 119.67(7) ?
    C9 C8 C7 . . 119.15(7) ?
    C9 C8 H8A . . 120.4 ?
    C7 C8 H8A . . 120.4 ?
    C8 C9 C10 . . 127.98(7) ?
    C8 C9 H9A . . 116.0 ?
    C10 C9 H9A . . 116.0 ?
    C11 C10 C15 . . 117.74(7) ?
    C11 C10 C9 . . 119.33(7) ?
    C15 C10 C9 . . 122.93(7) ?
    O2 C11 C12 . . 122.50(7) ?
    O2 C11 C10 . . 116.34(7) ?
    C12 C11 C10 . . 121.15(7) ?
    C13 C12 C11 . . 119.87(7) ?
    C13 C12 H12A . . 120.1 ?
    C11 C12 H12A . . 120.1 ?
    O3 C13 C12 . . 124.56(7) ?
    O3 C13 C14 . . 115.43(6) ?
    C12 C13 C14 . . 120.00(7) ?
    O4 C14 C15 . . 125.78(7) ?
    O4 C14 C13 . . 114.88(7) ?
    C15 C14 C13 . . 119.33(7) ?
    C14 C15 C10 . . 121.75(7) ?
    C14 C15 H15A . . 119.1 ?
    C10 C15 H15A . . 119.1 ?
    O2 C16 H16A . . 109.5 ?
    O2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O4 C18 H18A . . 109.5 ?
    O4 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O4 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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 . . . . -1.07(12) ?
    C1 C2 C3 F1 . . . . -179.57(7) ?
    C1 C2 C3 C4 . . . . -0.07(13) ?
    F1 C3 C4 C5 . . . . -179.26(7) ?
    C2 C3 C4 C5 . . . . 1.24(13) ?
    C3 C4 C5 C6 . . . . -1.31(12) ?
    C4 C5 C6 C1 . . . . 0.23(11) ?
    C4 C5 C6 C7 . . . . -178.60(7) ?
    C2 C1 C6 C5 . . . . 0.99(12) ?
    C2 C1 C6 C7 . . . . 179.73(7) ?
    C5 C6 C7 O1 . . . . 5.38(11) ?
    C1 C6 C7 O1 . . . . -173.38(8) ?
    C5 C6 C7 C8 . . . . -173.66(7) ?
    C1 C6 C7 C8 . . . . 7.58(11) ?
    O1 C7 C8 C9 . . . . -2.77(12) ?
    C6 C7 C8 C9 . . . . 176.26(7) ?
    C7 C8 C9 C10 . . . . -176.86(7) ?
    C8 C9 C10 C11 . . . . -172.71(8) ?
    C8 C9 C10 C15 . . . . 7.35(13) ?
    C16 O2 C11 C12 . . . . 12.28(11) ?
    C16 O2 C11 C10 . . . . -168.59(7) ?
    C15 C10 C11 O2 . . . . 176.97(7) ?
    C9 C10 C11 O2 . . . . -2.97(11) ?
    C15 C10 C11 C12 . . . . -3.88(11) ?
    C9 C10 C11 C12 . . . . 176.17(7) ?
    O2 C11 C12 C13 . . . . -177.69(7) ?
    C10 C11 C12 C13 . . . . 3.22(12) ?
    C17 O3 C13 C12 . . . . -2.21(12) ?
    C17 O3 C13 C14 . . . . 176.47(7) ?
    C11 C12 C13 O3 . . . . 178.87(7) ?
    C11 C12 C13 C14 . . . . 0.25(11) ?
    C18 O4 C14 C15 . . . . 12.27(12) ?
    C18 O4 C14 C13 . . . . -167.30(7) ?
    O3 C13 C14 O4 . . . . -2.06(10) ?
    C12 C13 C14 O4 . . . . 176.68(7) ?
    O3 C13 C14 C15 . . . . 178.33(7) ?
    C12 C13 C14 C15 . . . . -2.92(11) ?
    O4 C14 C15 C10 . . . . -177.35(7) ?
    C13 C14 C15 C10 . . . . 2.21(12) ?
    C11 C10 C15 C14 . . . . 1.14(11) ?
    C9 C10 C15 C14 . . . . -178.91(7) ?
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
    C18 H18C Cg 2_675 0.96 2.80 3.6930(10)
                                         155 y
    C4 H4A O4 1_546 0.93 2.40 3.2690(10)
                                       156 y
    C5 H5A O1 1_555 0.93 2.43 2.7510(10)
                                       100 y
    C9 H9A O1 1_555 0.93 2.40 2.7640(10)
                                       103 y
    C9 H9A O2 1_555 0.93 2.34 2.7230(10)
                                       104 y
    C18 H18B O1 2_665 0.96 2.46 3.3790(10)
                                         161 y
