##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-05
_journal_date_accepted     2010-07-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     o1995
_journal_page_last     o1995
_journal_paper_category     QO
_journal_coeditor_code     CI5129
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435, USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '603 358-2563'
_publ_section_title
;
(E)-1-(4-Bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Pek, Albert E.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Narayana, B.'
;
Department of Studies in Chemistry
Mangalore University
Mangalagangotri 574 199, India
;
    'Kamath, Prakash K.'
;
Department of Studies in Physics
Mangalore University
Mangalagangotri 574 199, India
;
    'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
data_I
_chemical_name_systematic
;
(E)-1-(4-Bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
;
_chemical_name_common     ?
_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/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     17.729(4)
_cell_length_b     4.3505(9)
_cell_length_c     19.335(4)
_cell_angle_alpha     90.00
_cell_angle_beta     116.93(3)
_cell_angle_gamma     90.00
_cell_volume     1329.6(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6810
_cell_measurement_theta_min     2.3629
_cell_measurement_theta_max     31.2337
_cell_measurement_temperature     100
_exptl_crystal_description     Block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.584
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     3.086
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.6740
_exptl_absorpt_correction_T_max     0.7462
_exptl_special_details
;
;
_diffrn_ambient_temperature     100
_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 APEXII CCD area-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19884
_diffrn_reflns_av_R_equivalents     0.0246
_diffrn_reflns_av_sigmaI/netI     0.0192
_diffrn_reflns_theta_min     1.29
_diffrn_reflns_theta_max     31.27
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.949
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -27
_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 >
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     4121
_reflns_number_gt     3635
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0298
_refine_ls_R_factor_gt     0.0244
_refine_ls_wR_factor_gt     0.0682
_refine_ls_wR_factor_ref     0.0697
_refine_ls_goodness_of_fit_ref     1.323
_refine_ls_restrained_S_all     1.323
_refine_ls_number_reflns     4121
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0363P)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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.670
_refine_diff_density_min     -0.218
_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'
    '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, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 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
    Br Br1 0.945523(8) -0.41655(3) 0.378517(7) 0.02597(6) Uani d . 1 . .
    O O1 0.68442(7) 0.3686(3) 0.49024(6) 0.0336(2) Uani d . 1 . .
    O O2 0.43404(7) 0.9395(2) 0.39362(6) 0.0264(2) Uani d . 1 . .
    C C1 0.73529(8) 0.1076(3) 0.41311(7) 0.0189(2) Uani d . 1 . .
    C C2 0.81716(8) 0.0874(3) 0.47366(7) 0.0220(2) Uani d . 1 . .
    H H2 0.8298 0.1829 0.5207 0.026 Uiso calc R 1 . .
    C C3 0.88004(8) -0.0719(3) 0.46513(7) 0.0231(3) Uani d . 1 . .
    H H3 0.9346 -0.0823 0.5056 0.028 Uiso calc R 1 . .
    C C4 0.85962(8) -0.2161(3) 0.39466(7) 0.0205(2) Uani d . 1 . .
    C C5 0.77855(8) -0.2084(3) 0.33435(7) 0.0218(2) Uani d . 1 . .
    H H5 0.7657 -0.3108 0.2881 0.026 Uiso calc R 1 . .
    C C6 0.71655(8) -0.0455(3) 0.34384(7) 0.0208(2) Uani d . 1 . .
    H H6 0.6618 -0.0383 0.3035 0.025 Uiso calc R 1 . .
    C C7 0.67125(8) 0.2954(3) 0.42458(7) 0.0217(2) Uani d . 1 . .
    C C8 0.59523(8) 0.3990(3) 0.35504(7) 0.0220(2) Uani d . 1 . .
    H H8 0.5869 0.3352 0.3062 0.026 Uiso calc R 1 . .
    C C9 0.53875(9) 0.5816(3) 0.36129(7) 0.0228(2) Uani d . 1 . .
    H H9 0.5472 0.6243 0.4114 0.027 Uiso calc R 1 . .
    C C10 0.46472(7) 0.7234(3) 0.29846(7) 0.0200(2) Uani d . 1 . .
    C C11 0.44482(8) 0.6850(3) 0.22024(7) 0.0236(2) Uani d . 1 . .
    H H11 0.4792 0.5618 0.2070 0.028 Uiso calc R 1 . .
    C C12 0.37500(9) 0.8268(3) 0.16228(7) 0.0261(3) Uani d . 1 . .
    H H12 0.3627 0.7990 0.1106 0.031 Uiso calc R 1 . .
    C C13 0.32339(9) 1.0104(3) 0.18148(8) 0.0264(3) Uani d . 1 . .
    H H13 0.2764 1.1052 0.1424 0.032 Uiso calc R 1 . .
    C C14 0.34131(8) 1.0537(3) 0.25838(8) 0.0242(3) Uani d . 1 . .
    H H14 0.3065 1.1775 0.2709 0.029 Uiso calc R 1 . .
    C C15 0.41145(8) 0.9114(3) 0.31666(7) 0.0204(2) Uani d . 1 . .
    C C16 0.38472(10) 1.1365(3) 0.41671(9) 0.0305(3) Uani d . 1 . .
    H H16A 0.3883 1.3440 0.4016 0.046 Uiso calc R 1 . .
    H H16B 0.4060 1.1269 0.4720 0.046 Uiso calc R 1 . .
    H H16C 0.3268 1.0706 0.3920 0.046 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 0.02597(8) 0.02800(8) 0.02547(8) 0.00666(5) 0.01300(6) 0.00312(5)
    O1 0.0330(5) 0.0476(6) 0.0203(4) 0.0095(5) 0.0120(4) -0.0023(4)
    O2 0.0279(5) 0.0312(5) 0.0211(4) 0.0059(4) 0.0120(4) -0.0031(4)
    C1 0.0210(6) 0.0194(5) 0.0173(5) -0.0001(4) 0.0097(4) 0.0022(4)
    C2 0.0236(6) 0.0248(6) 0.0168(5) -0.0009(5) 0.0086(5) 0.0000(4)
    C3 0.0215(6) 0.0266(6) 0.0189(5) 0.0007(5) 0.0071(5) 0.0027(4)
    C4 0.0236(6) 0.0185(5) 0.0217(5) 0.0022(4) 0.0122(4) 0.0037(4)
    C5 0.0262(6) 0.0204(6) 0.0187(5) 0.0006(5) 0.0101(5) -0.0001(4)
    C6 0.0217(6) 0.0203(6) 0.0184(5) -0.0017(4) 0.0074(4) 0.0001(4)
    C7 0.0226(6) 0.0233(6) 0.0203(5) -0.0004(5) 0.0108(4) 0.0001(4)
    C8 0.0222(6) 0.0245(6) 0.0193(5) -0.0009(5) 0.0092(4) -0.0015(4)
    C9 0.0222(6) 0.0267(6) 0.0200(5) -0.0026(5) 0.0100(5) -0.0039(4)
    C10 0.0187(5) 0.0203(5) 0.0214(5) -0.0033(4) 0.0094(4) -0.0028(4)
    C11 0.0253(6) 0.0236(6) 0.0234(6) -0.0033(5) 0.0124(5) -0.0046(5)
    C12 0.0304(7) 0.0261(6) 0.0190(5) -0.0047(5) 0.0089(5) -0.0015(5)
    C13 0.0233(6) 0.0246(6) 0.0260(6) -0.0021(5) 0.0064(5) 0.0015(5)
    C14 0.0217(6) 0.0222(6) 0.0284(6) -0.0010(5) 0.0110(5) -0.0013(5)
    C15 0.0203(6) 0.0197(6) 0.0217(6) -0.0038(4) 0.0100(5) -0.0031(4)
    C16 0.0345(7) 0.0325(7) 0.0310(7) 0.0052(6) 0.0206(6) -0.0036(5)
_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
    Br1 C4 . 1.8993(13) ?
    O1 C7 . 1.2243(16) ?
    O2 C15 . 1.3600(15) ?
    O2 C16 . 1.4325(16) ?
    C1 C6 . 1.3945(17) ?
    C1 C2 . 1.3950(18) ?
    C1 C7 . 1.4946(17) ?
    C2 C3 . 1.3846(19) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.3907(17) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.3817(18) ?
    C5 C6 . 1.3882(18) ?
    C5 H5 . 0.93 ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.4787(18) ?
    C8 C9 . 1.3259(18) ?
    C8 H8 . 0.93 ?
    C9 C10 . 1.4611(18) ?
    C9 H9 . 0.93 ?
    C10 C11 . 1.3987(17) ?
    C10 C15 . 1.4090(17) ?
    C11 C12 . 1.383(2) ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.386(2) ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.3853(19) ?
    C13 H13 . 0.93 ?
    C14 C15 . 1.3894(18) ?
    C14 H14 . 0.93 ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
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
    C15 O2 C16 . . 118.42(11) ?
    C6 C1 C2 . . 118.74(12) ?
    C6 C1 C7 . . 122.47(11) ?
    C2 C1 C7 . . 118.79(11) ?
    C3 C2 C1 . . 121.29(12) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 118.44(12) ?
    C2 C3 H3 . . 120.8 ?
    C4 C3 H3 . . 120.8 ?
    C5 C4 C3 . . 121.71(12) ?
    C5 C4 Br1 . . 118.52(9) ?
    C3 C4 Br1 . . 119.72(10) ?
    C4 C5 C6 . . 118.96(11) ?
    C4 C5 H5 . . 120.5 ?
    C6 C5 H5 . . 120.5 ?
    C5 C6 C1 . . 120.82(12) ?
    C5 C6 H6 . . 119.6 ?
    C1 C6 H6 . . 119.6 ?
    O1 C7 C8 . . 122.06(12) ?
    O1 C7 C1 . . 119.67(12) ?
    C8 C7 C1 . . 118.20(11) ?
    C9 C8 C7 . . 120.98(12) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C8 C9 C10 . . 127.46(12) ?
    C8 C9 H9 . . 116.3 ?
    C10 C9 H9 . . 116.3 ?
    C11 C10 C15 . . 118.03(11) ?
    C11 C10 C9 . . 122.71(12) ?
    C15 C10 C9 . . 119.25(11) ?
    C12 C11 C10 . . 121.20(13) ?
    C12 C11 H11 . . 119.4 ?
    C10 C11 H11 . . 119.4 ?
    C11 C12 C13 . . 119.82(12) ?
    C11 C12 H12 . . 120.1 ?
    C13 C12 H12 . . 120.1 ?
    C12 C13 C14 . . 120.49(13) ?
    C12 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C13 C14 C15 . . 119.74(13) ?
    C13 C14 H14 . . 120.1 ?
    C15 C14 H14 . . 120.1 ?
    O2 C15 C14 . . 124.01(12) ?
    O2 C15 C10 . . 115.27(11) ?
    C14 C15 C10 . . 120.73(12) ?
    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 . . . . 2.17(18) ?
    C7 C1 C2 C3 . . . . -177.12(11) ?
    C1 C2 C3 C4 . . . . -0.75(18) ?
    C2 C3 C4 C5 . . . . -1.24(18) ?
    C2 C3 C4 Br1 . . . . 176.31(9) ?
    C3 C4 C5 C6 . . . . 1.73(18) ?
    Br1 C4 C5 C6 . . . . -175.85(9) ?
    C4 C5 C6 C1 . . . . -0.24(18) ?
    C2 C1 C6 C5 . . . . -1.67(18) ?
    C7 C1 C6 C5 . . . . 177.60(11) ?
    C6 C1 C7 O1 . . . . 164.07(13) ?
    C2 C1 C7 O1 . . . . -16.66(18) ?
    C6 C1 C7 C8 . . . . -18.73(18) ?
    C2 C1 C7 C8 . . . . 160.54(11) ?
    O1 C7 C8 C9 . . . . 1.3(2) ?
    C1 C7 C8 C9 . . . . -175.87(12) ?
    C7 C8 C9 C10 . . . . 174.50(12) ?
    C8 C9 C10 C11 . . . . -1.3(2) ?
    C8 C9 C10 C15 . . . . 179.82(12) ?
    C15 C10 C11 C12 . . . . 0.01(19) ?
    C9 C10 C11 C12 . . . . -178.89(13) ?
    C10 C11 C12 C13 . . . . -0.1(2) ?
    C11 C12 C13 C14 . . . . 0.2(2) ?
    C12 C13 C14 C15 . . . . -0.2(2) ?
    C16 O2 C15 C14 . . . . -2.45(19) ?
    C16 O2 C15 C10 . . . . 177.64(11) ?
    C13 C14 C15 O2 . . . . -179.85(12) ?
    C13 C14 C15 C10 . . . . 0.06(19) ?
    C11 C10 C15 O2 . . . . 179.93(11) ?
    C9 C10 C15 O2 . . . . -1.13(17) ?
    C11 C10 C15 C14 . . . . 0.01(18) ?
    C9 C10 C15 C14 . . . . 178.95(11) ?
