##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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#            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     2006-09-21
_journal_date_accepted     2006-09-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o4798
_journal_page_last     o4799
_journal_paper_category     EO
_journal_coeditor_code     GG2012
_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
;
3-(3-Bromophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'P. S. Patil' ?
;     Department of Studies in Physics
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
    'Mohd Mustaqim Rosli' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    '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
;
    'Vedavati G. Puranik' ?
;     Centre for Materials Characterisation
      National Chemical Laboratory
      Pune 411 008
      India
;
    '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
;
3-(3-Bromophenyl)-1-(4-meyhoxyphenyl)prop-2-en-1-one
;
_chemical_name_common
;
3-(3-Bromophenyl)-1-(4-meyhoxyphenyl)prop-2-en-1-one
;
_chemical_formula_moiety     'C16 H13 Br O2'
_chemical_formula_sum     'C16 H13 Br O2'
_chemical_formula_iupac     'C16 H13 Br O2'
_chemical_formula_weight     317.17
_chemical_melting_point     ?
_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     10.29170(10)
_cell_length_b     3.89700(10)
_cell_length_c     17.0919(2)
_cell_angle_alpha     90.00
_cell_angle_beta     107.3130(10)
_cell_angle_gamma     90.00
_cell_volume     654.459(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7113
_cell_measurement_theta_min     2.73
_cell_measurement_theta_max     37.50
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     Block
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.37
_exptl_crystal_density_diffrn     1.610
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     320
_exptl_absorpt_coefficient_mu     3.135
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.369
_exptl_absorpt_correction_T_max     0.391
_exptl_special_details
;
The data was collected with the Oxford Cyrosystem
Cobra low-temperature attachment.
;
_diffrn_ambient_temperature     100.0(10)
_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 area-detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     31059
_diffrn_reflns_av_R_equivalents     0.027
_diffrn_reflns_av_sigmaI/netI     0.039
_diffrn_reflns_theta_min     1.25
_diffrn_reflns_theta_max     37.50
_diffrn_reflns_theta_full     37.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     28
_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     6812
_reflns_number_gt     6194
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0289
_refine_ls_R_factor_gt     0.0235
_refine_ls_wR_factor_gt     0.0568
_refine_ls_wR_factor_ref     0.0674
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_restrained_S_all     1.083
_refine_ls_number_reflns     6812
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0342P)²] 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     0.001
_refine_diff_density_max     0.64
_refine_diff_density_min     -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 2981 Friedel pairs'
_refine_ls_abs_structure_Flack     0.008(5)
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'
    'Br' 'Br' -0.2901 2.4595
                         '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
    Br Br1 0.357551(11) 0.79782(5) 0.574543(6) 0.02143(3) Uani d . 1 . .
    O O1 0.28008(10) 0.9906(3) 0.10248(7) 0.0264(2) Uani d . 1 . .
    O O2 0.91154(9) 1.0452(3) 0.14142(6) 0.02069(17) Uani d . 1 . .
    C C1 0.63215(12) 0.8777(3) 0.22358(8) 0.0174(2) Uani d . 1 . .
    H H1A 0.6200 0.7819 0.2707 0.021 Uiso calc R 1 . .
    C C2 0.76174(12) 0.9006(3) 0.21518(8) 0.0187(2) Uani d . 1 . .
    H H2A 0.8362 0.8197 0.2566 0.022 Uiso calc R 1 . .
    C C3 0.78077(11) 1.0448(3) 0.14462(8) 0.01631(18) Uani d . 1 . .
    C C4 0.67021(12) 1.1740(3) 0.08284(8) 0.01701(18) Uani d . 1 . .
    H H4A 0.6829 1.2756 0.0364 0.020 Uiso calc R 1 . .
    C C5 0.54069(11) 1.1481(3) 0.09195(7) 0.01675(19) Uani d . 1 . .
    H H5A 0.4666 1.2326 0.0508 0.020 Uiso calc R 1 . .
    C C6 0.51905(11) 0.9985(3) 0.16124(7) 0.01585(18) Uani d . 1 . .
    C C7 0.37727(12) 0.9554(3) 0.16440(8) 0.0184(2) Uani d . 1 . .
    C C8 0.35654(12) 0.8662(3) 0.24421(8) 0.0190(2) Uani d . 1 . .
    H H8A 0.4259 0.9089 0.2923 0.023 Uiso calc R 1 . .
    C C9 0.24013(12) 0.7255(3) 0.24851(8) 0.0180(2) Uani d . 1 . .
    H H9A 0.1745 0.6783 0.1990 0.022 Uiso calc R 1 . .
    C C10 0.20588(11) 0.6387(3) 0.32349(8) 0.01608(18) Uani d . 1 . .
    C C11 0.08441(11) 0.4626(3) 0.31654(8) 0.01783(19) Uani d . 1 . .
    H H11A 0.0293 0.3963 0.2651 0.021 Uiso calc R 1 . .
    C C12 0.04532(12) 0.3856(3) 0.38569(9) 0.0199(2) Uani d . 1 . .
    H H12A -0.0359 0.2697 0.3801 0.024 Uiso calc R 1 . .
    C C13 0.12654(12) 0.4804(3) 0.46296(8) 0.0186(2) Uani d . 1 . .
    H H13A 0.1009 0.4290 0.5094 0.022 Uiso calc R 1 . .
    C C14 0.24757(11) 0.6546(3) 0.46931(7) 0.01674(19) Uani d . 1 . .
    C C15 0.28875(11) 0.7349(3) 0.40159(7) 0.0165(2) Uani d . 1 . .
    H H15A 0.3701 0.8508 0.4076 0.020 Uiso calc R 1 . .
    C C16 0.93644(13) 1.1917(4) 0.07045(9) 0.0230(2) Uani d . 1 . .
    H H16A 1.0320 1.1802 0.0760 0.034 Uiso calc R 1 . .
    H H16B 0.9075 1.4270 0.0651 0.034 Uiso calc R 1 . .
    H H16C 0.8865 1.0662 0.0226 0.034 Uiso calc R 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
    Br1 0.02897(5) 0.01920(5) 0.01360(5) 0.00116(6) 0.00248(3) -0.00054(5)
    O1 0.0187(4) 0.0426(6) 0.0166(4) -0.0007(4) 0.0033(3) 0.0031(4)
    O2 0.0161(3) 0.0288(5) 0.0178(4) 0.0003(3) 0.0060(3) 0.0010(3)
    C1 0.0185(4) 0.0204(5) 0.0129(4) 0.0011(3) 0.0042(3) 0.0010(3)
    C2 0.0182(4) 0.0221(5) 0.0146(5) 0.0018(4) 0.0033(3) 0.0012(4)
    C3 0.0172(4) 0.0177(4) 0.0142(5) -0.0004(3) 0.0049(3) -0.0018(4)
    C4 0.0189(4) 0.0184(4) 0.0136(5) -0.0011(4) 0.0046(3) 0.0003(4)
    C5 0.0175(4) 0.0185(5) 0.0131(5) -0.0005(4) 0.0028(3) 0.0006(4)
    C6 0.0168(4) 0.0179(4) 0.0127(5) -0.0004(3) 0.0042(3) -0.0008(4)
    C7 0.0174(4) 0.0227(5) 0.0154(5) -0.0007(4) 0.0055(4) -0.0001(4)
    C8 0.0197(4) 0.0241(6) 0.0138(5) -0.0032(4) 0.0057(3) -0.0011(4)
    C9 0.0185(4) 0.0216(6) 0.0143(5) -0.0009(3) 0.0055(3) 0.0000(3)
    C10 0.0154(4) 0.0179(5) 0.0150(5) 0.0003(3) 0.0045(3) 0.0002(4)
    C11 0.0161(4) 0.0191(5) 0.0176(5) -0.0004(4) 0.0039(4) 0.0001(4)
    C12 0.0180(4) 0.0212(5) 0.0214(6) -0.0010(3) 0.0070(4) 0.0016(4)
    C13 0.0203(4) 0.0188(5) 0.0189(5) 0.0019(4) 0.0089(4) 0.0027(4)
    C14 0.0193(4) 0.0158(5) 0.0146(5) 0.0023(4) 0.0042(3) 0.0004(4)
    C15 0.0167(4) 0.0183(6) 0.0142(4) -0.0001(3) 0.0044(3) 0.0000(3)
    C16 0.0232(5) 0.0271(5) 0.0218(6) -0.0002(4) 0.0115(4) 0.0014(5)
_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
    Br1 C14 . 1.9017(12) ?
    O1 C7 . 1.2286(16) ?
    O2 C3 . 1.3632(14) ?
    O2 C16 . 1.4312(18) ?
    C1 C2 . 1.3861(16) ?
    C1 C6 . 1.4048(16) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.3961(18) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.3957(17) ?
    C4 C5 . 1.3910(16) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.3960(17) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.4857(16) ?
    C7 C8 . 1.4833(18) ?
    C8 C9 . 1.3391(16) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.4664(17) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.4000(16) ?
    C10 C15 . 1.4042(17) ?
    C11 C12 . 1.3898(19) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.3865(19) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.3941(17) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.3818(17) ?
    C15 H15A . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 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
    C3 O2 C16 . . 117.54(10) ?
    C2 C1 C6 . . 120.37(11) ?
    C2 C1 H1A . . 119.8 ?
    C6 C1 H1A . . 119.8 ?
    C1 C2 C3 . . 120.13(11) ?
    C1 C2 H2A . . 119.9 ?
    C3 C2 H2A . . 119.9 ?
    O2 C3 C4 . . 124.17(11) ?
    O2 C3 C2 . . 115.41(10) ?
    C4 C3 C2 . . 120.42(11) ?
    C5 C4 C3 . . 118.80(11) ?
    C5 C4 H4A . . 120.6 ?
    C3 C4 H4A . . 120.6 ?
    C4 C5 C6 . . 121.70(11) ?
    C4 C5 H5A . . 119.2 ?
    C6 C5 H5A . . 119.2 ?
    C5 C6 C1 . . 118.55(10) ?
    C5 C6 C7 . . 118.98(10) ?
    C1 C6 C7 . . 122.38(11) ?
    O1 C7 C8 . . 121.02(11) ?
    O1 C7 C6 . . 120.84(11) ?
    C8 C7 C6 . . 118.14(11) ?
    C9 C8 C7 . . 121.48(11) ?
    C9 C8 H8A . . 119.3 ?
    C7 C8 H8A . . 119.3 ?
    C8 C9 C10 . . 126.44(11) ?
    C8 C9 H9A . . 116.8 ?
    C10 C9 H9A . . 116.8 ?
    C11 C10 C15 . . 119.07(11) ?
    C11 C10 C9 . . 118.68(11) ?
    C15 C10 C9 . . 122.23(10) ?
    C12 C11 C10 . . 120.72(12) ?
    C12 C11 H11A . . 119.6 ?
    C10 C11 H11A . . 119.6 ?
    C13 C12 C11 . . 120.50(11) ?
    C13 C12 H12A . . 119.8 ?
    C11 C12 H12A . . 119.8 ?
    C12 C13 C14 . . 118.38(11) ?
    C12 C13 H13A . . 120.8 ?
    C14 C13 H13A . . 120.8 ?
    C15 C14 C13 . . 122.33(11) ?
    C15 C14 Br1 . . 118.76(9) ?
    C13 C14 Br1 . . 118.89(9) ?
    C14 C15 C10 . . 119.01(10) ?
    C14 C15 H15A . . 120.5 ?
    C10 C15 H15A . . 120.5 ?
    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 ?
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 . . . . 0.15(19) ?
    C16 O2 C3 C4 . . . . 0.81(18) ?
    C16 O2 C3 C2 . . . . -179.74(12) ?
    C1 C2 C3 O2 . . . . -178.05(11) ?
    C1 C2 C3 C4 . . . . 1.43(19) ?
    O2 C3 C4 C5 . . . . 177.76(12) ?
    C2 C3 C4 C5 . . . . -1.67(18) ?
    C3 C4 C5 C6 . . . . 0.35(19) ?
    C4 C5 C6 C1 . . . . 1.18(19) ?
    C4 C5 C6 C7 . . . . -175.49(12) ?
    C2 C1 C6 C5 . . . . -1.43(18) ?
    C2 C1 C6 C7 . . . . 175.13(12) ?
    C5 C6 C7 O1 . . . . 13.2(2) ?
    C1 C6 C7 O1 . . . . -163.35(14) ?
    C5 C6 C7 C8 . . . . -167.25(12) ?
    C1 C6 C7 C8 . . . . 16.21(18) ?
    O1 C7 C8 C9 . . . . 19.6(2) ?
    C6 C7 C8 C9 . . . . -159.93(12) ?
    C7 C8 C9 C10 . . . . -177.52(12) ?
    C8 C9 C10 C11 . . . . -173.94(13) ?
    C8 C9 C10 C15 . . . . 7.93(19) ?
    C15 C10 C11 C12 . . . . 0.51(18) ?
    C9 C10 C11 C12 . . . . -177.68(11) ?
    C10 C11 C12 C13 . . . . -0.39(19) ?
    C11 C12 C13 C14 . . . . 0.14(19) ?
    C12 C13 C14 C15 . . . . -0.02(18) ?
    C12 C13 C14 Br1 . . . . 178.23(9) ?
    C13 C14 C15 C10 . . . . 0.15(17) ?
    Br1 C14 C15 C10 . . . . -178.11(9) ?
    C11 C10 C15 C14 . . . . -0.38(17) ?
    C9 C10 C15 C14 . . . . 177.74(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
    _geom_hbond_publ_flag
    C11 H11A O2 1_445 0.93 2.51 3.4060(16) 163 y
    C16 H16A O1 1_655 0.96 2.57 3.5028(18) 165 y
