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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 2.4.    #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,5-Bis(5-bromo-2-thienyl)thiophene
;
_chemical_name_common      3157
_chemical_formula_moiety     'C12 H6 Br2 S3'
_chemical_formula_sum     'C12 H6 Br2 S3'
_chemical_formula_iupac     'C12 H6 Br2 S3'
_chemical_formula_weight     406.17
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P c c 2'
_symmetry_space_group_name_Hall     'P 2 -2c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x, -y, z+1/2'
    '-x, y, z+1/2'
_cell_length_a     7.6216(16)
_cell_length_b     30.003(6)
_cell_length_c     5.8841(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1345.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     903
_cell_measurement_theta_min     2.671
_cell_measurement_theta_max     27.463
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     2.005
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     6.462
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2008a)'
_exptl_absorpt_correction_T_min     0.1844
_exptl_absorpt_correction_T_max     0.5242
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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     'Siemens SMART Platform CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9565
_diffrn_reflns_av_R_equivalents     0.0345
_diffrn_reflns_av_sigmaI/netI     0.0368
_diffrn_reflns_theta_min     2.67
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -38
_diffrn_reflns_limit_k_max     38
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     ?
_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.
The structure refined as a merohedral inversion twin, whose mass ratio
converged to 61:39.
;
_reflns_number_total     3045
_reflns_number_gt     2818
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0584
_refine_ls_R_factor_gt     0.0528
_refine_ls_wR_factor_gt     0.1121
_refine_ls_wR_factor_ref     0.1139
_refine_ls_goodness_of_fit_ref     1.250
_refine_ls_restrained_S_all     1.249
_refine_ls_number_reflns     3045
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0403P)²+2.9087P] 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     1.237
_refine_diff_density_min     -0.619
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1341 Friedel pairs'
_refine_ls_abs_structure_Flack     0.00(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'
    '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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008b)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008b)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008b)'
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 0.69877(9) 0.96042(2) 1.02236(11) 0.0374(2) Uani d . 1 . .
    Br Br2 0.71126(13) 0.54014(2) 0.07093(13) 0.0532(3) Uani d . 1 . .
    S S1 0.6713(2) 0.86007(5) 0.9031(3) 0.0271(3) Uani d . 1 . .
    S S2 0.81817(19) 0.76622(5) 0.3646(3) 0.0232(3) Uani d . 1 . .
    S S3 0.6749(2) 0.62433(5) 0.3757(3) 0.0279(3) Uani d . 1 . .
    C C1 0.7418(8) 0.9124(2) 0.8288(11) 0.0253(13) Uani d . 1 . .
    C C2 0.8278(8) 0.9124(2) 0.6263(12) 0.0287(14) Uani d . 1 . .
    H H2 0.8761 0.9384 0.5584 0.034 Uiso calc R 1 . .
    C C3 0.8376(7) 0.86976(19) 0.5284(11) 0.0238(12) Uani d . 1 . .
    H H3 0.8933 0.8642 0.3868 0.029 Uiso calc R 1 . .
    C C4 0.7597(7) 0.8370(2) 0.6553(10) 0.0215(12) Uani d . 1 . .
    C C5 0.7360(7) 0.7908(2) 0.6122(10) 0.0172(12) Uani d . 1 . .
    C C6 0.6539(7) 0.75937(18) 0.7416(10) 0.0197(12) Uani d . 1 . .
    H H6 0.6009 0.7660 0.8838 0.024 Uiso calc R 1 . .
    C C7 0.6546(7) 0.71661(19) 0.6471(10) 0.0201(12) Uani d . 1 . .
    H H7 0.6016 0.6916 0.7182 0.024 Uiso calc R 1 . .
    C C8 0.7397(8) 0.71439(19) 0.4407(12) 0.0190(12) Uani d . 1 . .
    C C9 0.7621(7) 0.67576(19) 0.2972(10) 0.0175(11) Uani d . 1 . .
    C C10 0.8467(8) 0.6726(2) 0.0932(10) 0.0233(12) Uani d . 1 . .
    H H10 0.9036 0.6972 0.0231 0.028 Uiso calc R 1 . .
    C C11 0.8421(8) 0.62914(19) -0.0055(11) 0.0249(12) Uani d . 1 . .
    H H11 0.8927 0.6216 -0.1479 0.030 Uiso calc R 1 . .
    C C12 0.7553(9) 0.5999(2) 0.1323(12) 0.0269(13) 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
    Br1 0.0447(4) 0.0317(4) 0.0359(4) 0.0053(3) 0.0051(4) -0.0089(3)
    Br2 0.0814(7) 0.0272(4) 0.0512(7) -0.0077(4) 0.0045(5) -0.0099(4)
    S1 0.0315(8) 0.0282(7) 0.0217(8) -0.0025(6) 0.0079(6) -0.0021(6)
    S2 0.0252(7) 0.0259(7) 0.0185(7) -0.0031(6) 0.0045(6) 0.0006(6)
    S3 0.0338(8) 0.0234(7) 0.0263(8) -0.0046(6) 0.0066(7) 0.0012(7)
    C1 0.028(3) 0.025(3) 0.023(3) 0.002(2) -0.005(3) -0.003(3)
    C2 0.023(3) 0.029(3) 0.035(3) -0.002(2) -0.003(3) 0.009(3)
    C3 0.026(3) 0.024(3) 0.021(3) 0.000(2) 0.006(3) 0.004(3)
    C4 0.018(3) 0.030(3) 0.017(3) 0.003(2) 0.000(2) 0.000(2)
    C5 0.012(3) 0.026(3) 0.013(3) -0.001(2) -0.003(2) -0.004(2)
    C6 0.019(3) 0.023(3) 0.017(3) -0.001(2) -0.001(2) 0.001(2)
    C7 0.012(3) 0.026(3) 0.022(3) 0.000(2) -0.001(2) 0.005(2)
    C8 0.014(2) 0.017(3) 0.026(3) -0.002(2) 0.004(2) 0.010(2)
    C9 0.016(3) 0.015(3) 0.021(3) 0.002(2) -0.001(2) 0.000(2)
    C10 0.020(3) 0.029(3) 0.021(3) 0.002(2) -0.001(2) 0.003(2)
    C11 0.028(3) 0.023(3) 0.024(3) 0.005(2) 0.004(3) -0.006(2)
    C12 0.035(3) 0.022(3) 0.024(3) -0.004(3) 0.000(3) -0.006(3)
_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 C1 . 1.864(6) ?
    Br2 C12 . 1.858(6) ?
    S1 C1 . 1.717(7) ?
    S1 C4 . 1.749(6) ?
    S2 C8 . 1.725(6) ?
    S2 C5 . 1.750(6) ?
    S3 C12 . 1.722(7) ?
    S3 C9 . 1.742(6) ?
    C1 C2 . 1.360(10) ?
    C2 C3 . 1.404(9) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.370(8) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.419(8) ?
    C5 C6 . 1.365(8) ?
    C6 C7 . 1.398(8) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.379(9) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.444(8) ?
    C9 C10 . 1.366(8) ?
    C10 C11 . 1.428(8) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.367(9) ?
    C11 H11 . 0.9500 ?
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
    C1 S1 C4 . . 91.7(3) ?
    C8 S2 C5 . . 92.3(3) ?
    C12 S3 C9 . . 91.2(3) ?
    C2 C1 S1 . . 111.9(5) ?
    C2 C1 Br1 . . 128.4(5) ?
    S1 C1 Br1 . . 119.8(4) ?
    C1 C2 C3 . . 112.7(6) ?
    C1 C2 H2 . . 123.6 ?
    C3 C2 H2 . . 123.6 ?
    C4 C3 C2 . . 114.0(6) ?
    C4 C3 H3 . . 123.0 ?
    C2 C3 H3 . . 123.0 ?
    C3 C4 C5 . . 131.2(5) ?
    C3 C4 S1 . . 109.7(5) ?
    C5 C4 S1 . . 119.1(4) ?
    C6 C5 C4 . . 129.3(5) ?
    C6 C5 S2 . . 109.7(4) ?
    C4 C5 S2 . . 121.0(4) ?
    C5 C6 C7 . . 114.3(5) ?
    C5 C6 H6 . . 122.9 ?
    C7 C6 H6 . . 122.9 ?
    C8 C7 C6 . . 113.4(5) ?
    C8 C7 H7 . . 123.3 ?
    C6 C7 H7 . . 123.3 ?
    C7 C8 C9 . . 127.6(5) ?
    C7 C8 S2 . . 110.4(5) ?
    C9 C8 S2 . . 122.1(5) ?
    C10 C9 C8 . . 128.7(5) ?
    C10 C9 S3 . . 110.6(4) ?
    C8 C9 S3 . . 120.7(4) ?
    C9 C10 C11 . . 114.2(6) ?
    C9 C10 H10 . . 122.9 ?
    C11 C10 H10 . . 122.9 ?
    C12 C11 C10 . . 110.9(5) ?
    C12 C11 H11 . . 124.5 ?
    C10 C11 H11 . . 124.5 ?
    C11 C12 S3 . . 113.0(5) ?
    C11 C12 Br2 . . 126.3(5) ?
    S3 C12 Br2 . . 120.6(4) ?
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
    C4 S1 C1 C2 . . . . 0.0(5) ?
    C4 S1 C1 Br1 . . . . -179.1(4) ?
    S1 C1 C2 C3 . . . . 0.1(7) ?
    Br1 C1 C2 C3 . . . . 179.1(5) ?
    C1 C2 C3 C4 . . . . -0.2(8) ?
    C2 C3 C4 C5 . . . . 177.2(6) ?
    C2 C3 C4 S1 . . . . 0.2(7) ?
    C1 S1 C4 C3 . . . . -0.1(5) ?
    C1 S1 C4 C5 . . . . -177.6(5) ?
    C3 C4 C5 C6 . . . . -178.4(7) ?
    S1 C4 C5 C6 . . . . -1.6(9) ?
    C3 C4 C5 S2 . . . . 2.0(9) ?
    S1 C4 C5 S2 . . . . 178.8(3) ?
    C8 S2 C5 C6 . . . . 0.2(5) ?
    C8 S2 C5 C4 . . . . 179.8(5) ?
    C4 C5 C6 C7 . . . . -180.0(5) ?
    S2 C5 C6 C7 . . . . -0.4(7) ?
    C5 C6 C7 C8 . . . . 0.4(7) ?
    C6 C7 C8 C9 . . . . -179.1(6) ?
    C6 C7 C8 S2 . . . . -0.3(6) ?
    C5 S2 C8 C7 . . . . 0.0(5) ?
    C5 S2 C8 C9 . . . . 179.0(5) ?
    C7 C8 C9 C10 . . . . -179.5(6) ?
    S2 C8 C9 C10 . . . . 1.8(9) ?
    C7 C8 C9 S3 . . . . 0.8(9) ?
    S2 C8 C9 S3 . . . . -178.0(3) ?
    C12 S3 C9 C10 . . . . 0.2(5) ?
    C12 S3 C9 C8 . . . . 180.0(5) ?
    C8 C9 C10 C11 . . . . -179.2(6) ?
    S3 C9 C10 C11 . . . . 0.6(7) ?
    C9 C10 C11 C12 . . . . -1.3(8) ?
    C10 C11 C12 S3 . . . . 1.4(7) ?
    C10 C11 C12 Br2 . . . . 178.2(5) ?
    C9 S3 C12 C11 . . . . -1.0(5) ?
    C9 S3 C12 Br2 . . . . -177.9(4) ?
data_global
_journal_date_recd_electronic     2009-07-25
_journal_date_accepted     2009-08-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      9
_journal_page_first     o2119
_journal_page_last     o2119
_journal_paper_category     QO
_journal_coeditor_code     NG2619
_publ_contact_author_name     'Mamoun M. Bader'
_publ_contact_author_address
;
Department of Chemistry
Pennsylvania State University at Hazleton
76 University Drive
Hazleton, PA 18202
USA
;
_publ_contact_author_email     mmb11@psu.edu
_publ_contact_author_fax     '570 450 3182'
_publ_contact_author_phone     '570 450 3385'
_publ_section_title
;
2,5-Bis(5-bromo-2-thienyl)thiophene
;
loop_
    _publ_author_name
    _publ_author_address
    'Bader, Mamoun M.'
;
Department of Chemistry
Pennsylvania State University at Hazleton
76 University Drive
Hazleton, PA 18202
USA
;
