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###        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/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1,2-Bis(3-bromo-4-methylphenyl)ethene
;
_chemical_name_common     trans-1,2-bis(3-bromo-4-methylphenyl)ethylene
_chemical_formula_moiety     'C16 H14 Br2'
_chemical_formula_sum     'C16 H14 Br2'
_chemical_formula_iupac     'C16 H14 Br2'
_chemical_formula_weight     366.09
_chemical_melting_point     424.75
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     -P2ybc
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.3301(4)
_cell_length_b     7.6499(5)
_cell_length_c     28.164(2)
_cell_angle_alpha     90.00
_cell_angle_beta     91.2080(10)
_cell_angle_gamma     90.00
_cell_volume     1363.55(16)
_cell_formula_units_Z     4
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.783
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     5.924
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2004)
;
_exptl_absorpt_correction_T_min     0.303
_exptl_absorpt_correction_T_max     0.578
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     14025
_diffrn_reflns_av_R_equivalents     0.0273
_diffrn_reflns_av_sigmaI/netI     0.0211
_diffrn_reflns_theta_min     2.76
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     35
_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     2793
_reflns_number_gt     2393
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0329
_refine_ls_R_factor_gt     0.0246
_refine_ls_wR_factor_gt     0.0512
_refine_ls_wR_factor_ref     0.0536
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.085
_refine_ls_number_reflns     2793
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0179P)²+1.6865P] 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     0.425
_refine_diff_density_min     -0.319
_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'
    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, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2003)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2006)'
_computing_publication_material     'publCIF (Westrip, 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 0.08255(4) 0.93057(4) 0.562520(9) 0.02689(8) Uani d . 1 . .
    C C1 0.0145(4) 0.8529(3) 0.62456(8) 0.0197(5) Uani d . 1 . .
    C C2 -0.1806(4) 0.7739(3) 0.63183(9) 0.0217(5) Uani d . 1 . .
    C C3 -0.2158(4) 0.7151(3) 0.67779(10) 0.0241(6) Uani d . 1 . .
    H H3 -0.3476 0.6620 0.6844 0.029 Uiso calc R 1 . .
    C C4 -0.0673(4) 0.7309(3) 0.71400(9) 0.0237(6) Uani d . 1 . .
    H H4 -0.0972 0.6867 0.7446 0.028 Uiso calc R 1 . .
    C C5 0.1280(4) 0.8119(3) 0.70600(9) 0.0213(6) Uani d . 1 . .
    C C6 0.1650(4) 0.8749(3) 0.66049(9) 0.0212(5) Uani d . 1 . .
    H H6 0.2939 0.9332 0.6541 0.025 Uiso calc R 1 . .
    C C7 0.2912(4) 0.8315(4) 0.74343(9) 0.0241(6) Uani d . 1 . .
    H H7 0.4101 0.9015 0.7361 0.029 Uiso calc R 1 . .
    C C8 -0.3452(4) 0.7506(4) 0.59307(10) 0.0282(6) Uani d . 1 . .
    H H8A -0.2872 0.6792 0.5676 0.034 Uiso calc R 1 . .
    H H8B -0.3865 0.8653 0.5804 0.034 Uiso calc R 1 . .
    H H8C -0.4693 0.6922 0.6060 0.034 Uiso calc R 1 . .
    Br Br2 0.44176(4) 0.73105(4) 0.971236(9) 0.02871(8) Uani d . 1 . .
    C C11 0.5297(4) 0.7870(3) 0.90906(9) 0.0205(5) Uani d . 1 . .
    C C12 0.7254(4) 0.8675(3) 0.90274(9) 0.0218(5) Uani d . 1 . .
    C C13 0.7768(4) 0.9044(3) 0.85612(10) 0.0243(6) Uani d . 1 . .
    H H13 0.9102 0.9558 0.8501 0.029 Uiso calc R 1 . .
    C C14 0.6420(4) 0.8695(4) 0.81816(9) 0.0253(6) Uani d . 1 . .
    H H14 0.6834 0.8991 0.7869 0.030 Uiso calc R 1 . .
    C C15 0.4454(4) 0.7913(3) 0.82503(9) 0.0218(6) Uani d . 1 . .
    C C16 0.3931(4) 0.7476(3) 0.87155(9) 0.0224(6) Uani d . 1 . .
    H H16 0.2629 0.6906 0.8774 0.027 Uiso calc R 1 . .
    C C17 0.2894(4) 0.7613(4) 0.78658(9) 0.0250(6) Uani d . 1 . .
    H H17 0.1761 0.6842 0.7932 0.030 Uiso calc R 1 . .
    C C18 0.8708(4) 0.9153(4) 0.94351(10) 0.0279(6) Uani d . 1 . .
    H H18A 0.8014 1.0011 0.9638 0.033 Uiso calc R 1 . .
    H H18B 1.0011 0.9656 0.9313 0.033 Uiso calc R 1 . .
    H H18C 0.9047 0.8104 0.9621 0.033 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 0.02994(15) 0.03138(16) 0.01930(14) -0.00196(12) -0.00088(10)
                                                                     0.00574(11)
    C1 0.0243(14) 0.0192(13) 0.0157(12) 0.0034(11) 0.0018(10) 0.0006(10)
    C2 0.0207(13) 0.0217(14) 0.0226(13) 0.0025(11) -0.0021(10) -0.0016(11)
    C3 0.0214(13) 0.0219(14) 0.0291(15) 0.0000(11) 0.0031(11) 0.0012(11)
    C4 0.0295(15) 0.0221(14) 0.0196(13) 0.0031(11) 0.0033(11) -0.0001(11)
    C5 0.0252(14) 0.0196(13) 0.0190(13) 0.0025(11) 0.0001(11) -0.0042(10)
    C6 0.0193(13) 0.0224(14) 0.0218(13) -0.0019(11) 0.0014(10) -0.0017(11)
    C7 0.0253(14) 0.0256(15) 0.0213(14) 0.0010(11) 0.0001(11) -0.0028(11)
    C8 0.0247(14) 0.0314(16) 0.0283(15) -0.0022(12) -0.0052(11) -0.0001(12)
    Br2 0.03120(16) 0.03709(17) 0.01781(14) -0.00261(12) -0.00030(11)
                                                                     0.00279(12)
    C11 0.0259(14) 0.0184(13) 0.0172(13) 0.0044(11) 0.0003(10) 0.0014(10)
    C12 0.0221(13) 0.0169(13) 0.0262(14) 0.0042(10) -0.0029(11) -0.0014(11)
    C13 0.0192(13) 0.0218(14) 0.0321(15) 0.0008(11) 0.0027(11) 0.0016(11)
    C14 0.0298(15) 0.0249(14) 0.0213(14) 0.0026(12) 0.0030(11) 0.0018(11)
    C15 0.0251(14) 0.0185(13) 0.0217(13) 0.0028(11) -0.0017(11) -0.0011(10)
    C16 0.0216(13) 0.0216(14) 0.0240(14) -0.0008(11) -0.0008(10) 0.0009(11)
    C17 0.0287(15) 0.0243(14) 0.0218(14) -0.0022(12) -0.0013(11) -0.0023(11)
    C18 0.0272(15) 0.0248(15) 0.0314(15) -0.0020(12) -0.0052(12) -0.0019(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
    Br1 C1 . 1.904(2) ?
    C1 C6 . 1.386(3) ?
    C1 C2 . 1.393(4) ?
    C2 C3 . 1.393(4) ?
    C2 C8 . 1.504(4) ?
    C3 C4 . 1.378(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.405(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.394(4) ?
    C5 C7 . 1.468(4) ?
    C6 H6 . 0.9500 ?
    C7 C17 . 1.329(4) ?
    C7 H7 . 0.9500 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    Br2 C11 . 1.898(3) ?
    C11 C16 . 1.385(4) ?
    C11 C12 . 1.398(4) ?
    C12 C13 . 1.389(4) ?
    C12 C18 . 1.502(4) ?
    C13 C14 . 1.380(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.398(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.399(4) ?
    C15 C17 . 1.468(4) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 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
    C6 C1 C2 . . 122.9(2) ?
    C6 C1 Br1 . . 117.82(19) ?
    C2 C1 Br1 . . 119.25(19) ?
    C3 C2 C1 . . 115.9(2) ?
    C3 C2 C8 . . 120.9(2) ?
    C1 C2 C8 . . 123.2(2) ?
    C4 C3 C2 . . 122.6(3) ?
    C4 C3 H3 . . 118.7 ?
    C2 C3 H3 . . 118.7 ?
    C3 C4 C5 . . 120.6(2) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C6 C5 C4 . . 117.7(2) ?
    C6 C5 C7 . . 119.7(2) ?
    C4 C5 C7 . . 122.6(2) ?
    C1 C6 C5 . . 120.2(2) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C17 C7 C5 . . 126.6(3) ?
    C17 C7 H7 . . 116.7 ?
    C5 C7 H7 . . 116.7 ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C16 C11 C12 . . 122.7(2) ?
    C16 C11 Br2 . . 117.7(2) ?
    C12 C11 Br2 . . 119.67(19) ?
    C13 C12 C11 . . 115.9(2) ?
    C13 C12 C18 . . 121.4(2) ?
    C11 C12 C18 . . 122.7(2) ?
    C14 C13 C12 . . 122.7(3) ?
    C14 C13 H13 . . 118.7 ?
    C12 C13 H13 . . 118.7 ?
    C13 C14 C15 . . 120.9(2) ?
    C13 C14 H14 . . 119.6 ?
    C15 C14 H14 . . 119.6 ?
    C14 C15 C16 . . 117.5(2) ?
    C14 C15 C17 . . 123.5(2) ?
    C16 C15 C17 . . 119.0(2) ?
    C11 C16 C15 . . 120.4(2) ?
    C11 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    C7 C17 C15 . . 126.4(3) ?
    C7 C17 H17 . . 116.8 ?
    C15 C17 H17 . . 116.8 ?
    C12 C18 H18A . . 109.5 ?
    C12 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C12 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
    Br2 C11 C12 C18 . . . . -1.0(3) ?
    Br1 C1 C2 C8 . . . . -1.7(4) ?
    C4 C5 C7 C17 . . . . 8.2(4) ?
    C14 C15 C17 C7 . . . . -14.1(4) ?
    C6 C5 C7 C17 . . . . -171.7(3) ?
    C16 C15 C17 C7 . . . . 162.7(3) ?
    C5 C7 C17 C15 . . . . -175.4(2) ?
data_global
_journal_date_recd_electronic     2007-12-15
_journal_date_accepted     2007-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o363
_journal_page_last     o363
_journal_paper_category     QO
_journal_coeditor_code     PV2061
_publ_contact_author_name     "Boeré, René T."
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
University of Lethbridge
Lethbridge, AB Canada
T1K 3M4
;
_publ_contact_author_email     boere@uleth.ca
_publ_contact_author_fax     +1-403-329-2057
_publ_contact_author_phone     +1-403-329-2045
_publ_section_title
;
(E)-1,2-Bis(3-bromo-4-methylphenyl)ethene
;
loop_
    _publ_author_name
    _publ_author_address
    "Boeré, René T."
;
 Department of Chemistry and Biochemistry
 University of Lethbridge
 Lethbridge, AB, Canada T1K 3M4
;
    'Robbins, Steven J.'
;
 Department of Chemistry and Biochemistry
 University of Lethbridge
 Lethbridge, AB, Canada T1K 3M4
;
_publ_section_synopsis     .
