##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2E)-1-(3-Bromo-2-thienyl)-3-(4-methoxyphenyl)prop-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Br O2 S'
_chemical_formula_sum     'C14 H11 Br O2 S'
_chemical_formula_iupac     'C14 H11 Br O2 S'
_chemical_formula_weight     323.20
_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     4.00250(10)
_cell_length_b     10.7048(3)
_cell_length_c     14.6451(5)
_cell_angle_alpha     90.00
_cell_angle_beta     91.789(2)
_cell_angle_gamma     90.00
_cell_volume     627.18(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1442
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.711
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     324
_exptl_absorpt_coefficient_mu     3.433
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.388
_exptl_absorpt_correction_T_max     0.795
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(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     'Nonius KappaCCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7197
_diffrn_reflns_av_R_equivalents     0.0241
_diffrn_reflns_av_sigmaI/netI     0.0487
_diffrn_reflns_theta_min     3.37
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_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     -18
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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     2705
_reflns_number_gt     2555
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0255
_refine_ls_R_factor_gt     0.0231
_refine_ls_wR_factor_gt     0.0549
_refine_ls_wR_factor_ref     0.0556
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     2705
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'calc w=1/[σ²(Fo²)+0.0736P] 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     0.000
_refine_diff_density_max     0.695
_refine_diff_density_min     -0.546
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.016(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 1198 Friedel pairs'
_refine_ls_abs_structure_Flack     0.013(7)
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'
    'S' 'S' 0.1246 0.1234
                         '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     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
;
SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing,
1995)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
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
    C C1 0.2423(6) -0.0427(2) -0.04736(17) 0.0193(5) Uani d . 1 . .
    H H1 0.2683 -0.0523 -0.1112 0.023 Uiso calc R 1 . .
    C C2 0.3344(6) 0.0614(2) -0.00015(17) 0.0184(5) Uani d . 1 . .
    H H2 0.4282 0.1337 -0.0269 0.022 Uiso calc R 1 . .
    C C3 0.2730(6) 0.0486(2) 0.09375(16) 0.0164(5) Uani d . 1 . .
    C C4 0.1342(5) -0.0634(2) 0.11667(16) 0.0156(5) Uani d . 1 . .
    C C5 0.0263(6) -0.1228(2) 0.20151(18) 0.0207(5) Uani d . 1 . .
    C C6 0.1591(6) -0.0777(3) 0.29061(18) 0.0224(5) Uani d . 1 . .
    H H6 0.3067 -0.0082 0.2934 0.027 Uiso calc R 1 . .
    C C7 0.0716(6) -0.1346(2) 0.36740(18) 0.0221(5) Uani d . 1 . .
    H H7 -0.0866 -0.2004 0.3608 0.026 Uiso calc R 1 . .
    C C8 0.1923(6) -0.1069(2) 0.46063(18) 0.0205(5) Uani d . 1 . .
    C C9 0.3797(6) -0.0006(2) 0.48433(18) 0.0220(5) Uani d . 1 . .
    H H9 0.4361 0.0566 0.4376 0.026 Uiso calc R 1 . .
    C C10 0.4853(6) 0.0241(2) 0.57303(18) 0.0221(5) Uani d . 1 . .
    H H10 0.6066 0.0981 0.5875 0.027 Uiso calc R 1 . .
    C C11 0.4104(6) -0.0621(3) 0.64133(18) 0.0194(5) Uani d . 1 . .
    C C12 0.2243(6) -0.1685(2) 0.62022(18) 0.0207(6) Uani d . 1 . .
    H H12 0.1722 -0.2264 0.6668 0.025 Uiso calc R 1 . .
    C C13 0.1154(6) -0.1897(2) 0.53092(17) 0.0215(5) Uani d . 1 . .
    H H13 -0.0144 -0.2619 0.5171 0.026 Uiso calc R 1 . .
    C C14 0.6933(6) 0.0627(3) 0.75581(19) 0.0251(6) Uani d . 1 . .
    H H14A 0.7517 0.0604 0.8213 0.038 Uiso calc R 1 . .
    H H14B 0.5541 0.1361 0.7424 0.038 Uiso calc R 1 . .
    H H14C 0.8979 0.0673 0.7209 0.038 Uiso calc R 1 . .
    O O1 -0.1577(5) -0.2146(2) 0.19520(14) 0.0293(4) Uani d . 1 . .
    O O2 0.5115(4) -0.04857(17) 0.73066(12) 0.0252(4) Uani d . 1 . .
    S S1 0.07572(15) -0.15396(5) 0.01985(4) 0.01747(14) Uani d . 1 . .
    Br Br1 0.36561(5) 0.18455(3) 0.172837(14) 0.02187(9) Uani d . 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
    C1 0.0257(12) 0.0204(12) 0.0121(12) 0.0067(10) 0.0037(9) 0.0018(10)
    C2 0.0190(11) 0.0179(12) 0.0186(13) 0.0024(9) 0.0038(9) 0.0024(10)
    C3 0.0173(11) 0.0168(12) 0.0148(12) 0.0011(9) -0.0026(9) -0.0016(10)
    C4 0.0170(10) 0.0155(12) 0.0141(12) 0.0008(9) -0.0026(9) -0.0009(10)
    C5 0.0266(12) 0.0185(13) 0.0170(14) 0.0042(10) 0.0006(10) 0.0034(10)
    C6 0.0241(12) 0.0245(13) 0.0187(14) -0.0001(11) -0.0002(10) 0.0014(11)
    C7 0.0230(12) 0.0225(13) 0.0207(15) 0.0009(11) 0.0004(10) 0.0005(11)
    C8 0.0238(12) 0.0227(13) 0.0153(13) 0.0068(10) 0.0045(10) 0.0018(10)
    C9 0.0245(12) 0.0196(13) 0.0223(14) 0.0048(10) 0.0068(10) 0.0077(11)
    C10 0.0205(11) 0.0201(12) 0.0260(15) 0.0002(11) 0.0036(10) 0.0050(11)
    C11 0.0167(10) 0.0250(13) 0.0167(13) 0.0062(10) 0.0046(9) 0.0042(11)
    C12 0.0201(12) 0.0251(14) 0.0172(14) 0.0040(10) 0.0041(10) 0.0100(11)
    C13 0.0259(12) 0.0182(12) 0.0206(14) 0.0021(10) 0.0041(10) 0.0034(10)
    C14 0.0216(12) 0.0295(14) 0.0240(15) 0.0039(11) -0.0014(10) -0.0022(11)
    O1 0.0318(10) 0.0298(11) 0.0262(11) -0.0097(8) 0.0006(8) 0.0079(9)
    O2 0.0282(9) 0.0273(10) 0.0199(10) -0.0009(8) -0.0034(7) 0.0036(8)
    S1 0.0220(3) 0.0143(3) 0.0159(3) -0.0006(2) -0.0015(2) -0.0022(2)
    Br1 0.02817(13) 0.01867(13) 0.01862(14) -0.00414(12) -0.00191(8)
                                                                    -0.00505(12)
_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
    C1 C2 . 1.357(4) ?
    C1 S1 . 1.695(3) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.411(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.368(3) ?
    C3 Br1 . 1.889(2) ?
    C4 C5 . 1.472(3) ?
    C4 S1 . 1.727(2) ?
    C5 O1 . 1.230(3) ?
    C5 C6 . 1.475(4) ?
    C6 C7 . 1.335(4) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.464(4) ?
    C7 H7 . 0.9500 ?
    C8 C13 . 1.400(4) ?
    C8 C9 . 1.401(4) ?
    C9 C10 . 1.379(4) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.400(4) ?
    C10 H10 . 0.9500 ?
    C11 O2 . 1.365(3) ?
    C11 C12 . 1.390(4) ?
    C12 C13 . 1.384(4) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 0.9500 ?
    C14 O2 . 1.437(3) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
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 C1 S1 . . 112.75(19) ?
    C2 C1 H1 . . 123.6 ?
    S1 C1 H1 . . 123.6 ?
    C1 C2 C3 . . 111.4(2) ?
    C1 C2 H2 . . 124.3 ?
    C3 C2 H2 . . 124.3 ?
    C4 C3 C2 . . 114.1(2) ?
    C4 C3 Br1 . . 126.74(18) ?
    C2 C3 Br1 . . 119.08(18) ?
    C3 C4 C5 . . 135.8(2) ?
    C3 C4 S1 . . 109.64(18) ?
    C5 C4 S1 . . 114.52(18) ?
    O1 C5 C4 . . 118.2(2) ?
    O1 C5 C6 . . 121.8(2) ?
    C4 C5 C6 . . 119.9(2) ?
    C7 C6 C5 . . 119.9(3) ?
    C7 C6 H6 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C6 C7 C8 . . 127.2(3) ?
    C6 C7 H7 . . 116.4 ?
    C8 C7 H7 . . 116.4 ?
    C13 C8 C9 . . 117.4(2) ?
    C13 C8 C7 . . 118.9(2) ?
    C9 C8 C7 . . 123.6(2) ?
    C10 C9 C8 . . 122.3(2) ?
    C10 C9 H9 . . 118.8 ?
    C8 C9 H9 . . 118.8 ?
    C9 C10 C11 . . 118.8(2) ?
    C9 C10 H10 . . 120.6 ?
    C11 C10 H10 . . 120.6 ?
    O2 C11 C12 . . 116.2(2) ?
    O2 C11 C10 . . 123.4(2) ?
    C12 C11 C10 . . 120.4(2) ?
    C13 C12 C11 . . 119.7(2) ?
    C13 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C12 C13 C8 . . 121.4(2) ?
    C12 C13 H13 . . 119.3 ?
    C8 C13 H13 . . 119.3 ?
    O2 C14 H14A . . 109.5 ?
    O2 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O2 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C11 O2 C14 . . 117.8(2) ?
    C1 S1 C4 . . 92.12(12) ?
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
    S1 C1 C2 C3 . . . . 1.2(3) ?
    C1 C2 C3 C4 . . . . -0.4(3) ?
    C1 C2 C3 Br1 . . . . -177.62(17) ?
    C2 C3 C4 C5 . . . . 179.6(2) ?
    Br1 C3 C4 C5 . . . . -3.5(4) ?
    C2 C3 C4 S1 . . . . -0.5(3) ?
    Br1 C3 C4 S1 . . . . 176.42(13) ?
    C3 C4 C5 O1 . . . . 164.0(3) ?
    S1 C4 C5 O1 . . . . -15.9(3) ?
    C3 C4 C5 C6 . . . . -20.6(4) ?
    S1 C4 C5 C6 . . . . 159.54(18) ?
    O1 C5 C6 C7 . . . . -2.1(4) ?
    C4 C5 C6 C7 . . . . -177.4(2) ?
    C5 C6 C7 C8 . . . . 176.5(2) ?
    C6 C7 C8 C13 . . . . -169.4(3) ?
    C6 C7 C8 C9 . . . . 11.3(4) ?
    C13 C8 C9 C10 . . . . -0.4(3) ?
    C7 C8 C9 C10 . . . . 178.9(2) ?
    C8 C9 C10 C11 . . . . 1.8(4) ?
    C9 C10 C11 O2 . . . . 178.0(2) ?
    C9 C10 C11 C12 . . . . -1.9(3) ?
    O2 C11 C12 C13 . . . . -179.3(2) ?
    C10 C11 C12 C13 . . . . 0.6(4) ?
    C11 C12 C13 C8 . . . . 0.9(4) ?
    C9 C8 C13 C12 . . . . -1.0(3) ?
    C7 C8 C13 C12 . . . . 179.7(2) ?
    C12 C11 O2 C14 . . . . -177.6(2) ?
    C10 C11 O2 C14 . . . . 2.5(3) ?
    C2 C1 S1 C4 . . . . -1.29(19) ?
    C3 C4 S1 C1 . . . . 1.00(18) ?
    C5 C4 S1 C1 . . . . -179.08(18) ?
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
    C1 H1 O2 1_554 0.95 2.54 3.457(3) 162
data_global
_journal_date_recd_electronic     2006-08-22
_journal_date_accepted     2006-08-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o4164
_journal_page_last     o4165
_journal_paper_category     EO
_journal_coeditor_code     BG2004
_publ_contact_author_name     'William T. A. Harrison'
_publ_contact_author_address
;
Department of Chemistry
University of Aberdeen
Aberdeen  AB24 3UE
UK
;
_publ_contact_author_email     w.harrison@abdn.ac.uk
_publ_contact_author_fax     ' 44 1224 272921 '
_publ_contact_author_phone     ' 44 1224 272897 '
_publ_section_title
;
(2E)-1-(3-Bromo-2-thienyl)-3-(4-methoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Harrison, William T. A.'
;   Department of Chemistry
    University of Aberdeen
    Meston Walk
    Aberdeen AB24 3UE
    Scotland
;
    'Yathirajan, H. S.'
;     Department of Studies in Chemistry
      University of Mysore
      Manasagangotri,
      Mysore 570 006,
      India
;
    'Ashalatha, B. V.'
;     Department of Chemistry,
      Mangalore University,
      Mangalagangotri 574 199,
      India
;
    'Bindya, S.'
;     Department of Chemistry,
      Sri Jayachamarajendra College of Engineering,
      Mysore 570 006,
      India
;
    'Narayana, B.'
;     Department of Chemistry,
      Mangalore University,
      Mangalagangotri 574 199,
      India
;
