##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1060721'
_audit_creation_method     SHELXL-2012
_chemical_name_systematic
;
4'-Bromo-2,3,5,6-tetrafluorobiphenyl-4-carbonitrile
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C13 H4 Br F4 N'
_chemical_formula_sum     'C13 H4 Br F4 N'
_chemical_formula_iupac     'C13 H4 Br F4 N'
_chemical_formula_weight     330.08
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     7.3560(15)
_cell_length_b     12.107(2)
_cell_length_c     12.723(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1133.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4750
_cell_measurement_theta_min     3.21
_cell_measurement_theta_max     28.42
_cell_measurement_temperature     93(2)
_exptl_crystal_description     'splitter'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.493
_exptl_crystal_size_mid     0.133
_exptl_crystal_size_min     0.097
_exptl_crystal_density_diffrn     1.935
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     3.663
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_shelx_estimated_absorpt_T_min     0.265
_shelx_estimated_absorpt_T_max     0.718
_exptl_absorpt_correction_T_min     0.486
_exptl_absorpt_correction_T_max     0.718
_exptl_special_details     ?
_diffrn_ambient_temperature     93(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18347
_diffrn_reflns_av_R_equivalents     0.0532
_diffrn_reflns_theta_min     2.322
_diffrn_reflns_theta_max     29.801
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_reflns_number_total     3234
_reflns_number_gt     2930
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0341
_refine_ls_R_factor_gt     0.0277
_refine_ls_wR_factor_gt     0.0505
_refine_ls_wR_factor_ref     0.0521
_refine_ls_goodness_of_fit_ref     0.987
_refine_ls_restrained_S_all     0.987
_refine_ls_number_reflns     3234
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0144P)²]
where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.463
_refine_diff_density_min     -0.311
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.011(9)
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'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2012 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010)
and SHELXLE
(Hübschle et al.,  2011)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.89811(4) 0.35795(3) 0.37922(2) 0.01853(8) Uani d 1 . .
    F F1 0.7744(2) 1.00596(16) 0.75920(12) 0.0196(4) Uani d 1 . .
    F F2 0.7639(2) 0.79698(15) 0.69387(12) 0.0179(4) Uani d 1 . .
    F F3 1.0359(2) 0.90632(14) 0.37137(13) 0.0163(4) Uani d 1 . .
    F F4 1.0323(2) 1.11450(14) 0.43493(13) 0.0196(4) Uani d 1 . .
    N N1 0.9005(4) 1.2681(2) 0.66563(19) 0.0208(6) Uani d 1 . .
    C C1 0.9026(4) 1.1790(2) 0.6343(2) 0.0161(6) Uani d 1 . .
    C C2 0.9029(5) 1.0664(2) 0.5984(2) 0.0153(6) Uani d 1 . .
    C C3 0.8371(4) 0.9812(3) 0.6627(2) 0.0154(7) Uani d 1 . .
    C C4 0.8354(4) 0.8729(3) 0.6295(2) 0.0147(6) Uani d 1 . .
    C C5 0.9004(4) 0.8418(2) 0.5296(2) 0.0131(6) Uani d 1 . .
    C C6 0.9650(4) 0.9283(3) 0.4667(2) 0.0129(6) Uani d 1 . .
    C C7 0.9665(4) 1.0369(3) 0.4992(2) 0.0144(6) Uani d 1 . .
    C C8 0.8998(5) 0.7249(2) 0.4938(2) 0.0133(6) Uani d 1 . .
    C C9 0.9476(4) 0.6389(3) 0.5620(2) 0.0145(6) Uani d 1 . .
    H H9 0.9807 0.6555 0.6324 0.017 Uiso calc 1 . .
    C C10 0.9474(4) 0.5302(3) 0.5286(2) 0.0161(7) Uani d 1 . .
    H H10 0.9795 0.4725 0.5756 0.019 Uiso calc 1 . .
    C C11 0.8997(5) 0.5065(2) 0.4254(2) 0.0148(6) Uani d 1 . .
    C C12 0.8517(4) 0.5894(3) 0.3554(2) 0.0153(7) Uani d 1 . .
    H H12 0.8191 0.5720 0.2851 0.018 Uiso calc 1 . .
    C C13 0.8520(4) 0.6986(3) 0.3898(2) 0.0142(6) Uani d 1 . .
    H H13 0.8196 0.7560 0.3424 0.017 Uiso calc 1 . .
_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 C11 . 1.892(3) ?
    F1 C3 . 1.346(3) ?
    F2 C4 . 1.339(3) ?
    F3 C6 . 1.347(3) ?
    F4 C7 . 1.336(3) ?
    N1 C1 . 1.150(4) ?
    C1 C2 . 1.438(4) ?
    C2 C7 . 1.393(4) ?
    C2 C3 . 1.402(4) ?
    C3 C4 . 1.377(4) ?
    C4 C5 . 1.409(4) ?
    C5 C6 . 1.401(4) ?
    C5 C8 . 1.487(4) ?
    C6 C7 . 1.379(4) ?
    C8 C9 . 1.400(4) ?
    C8 C13 . 1.406(4) ?
    C9 C10 . 1.383(4) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.389(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.388(4) ?
    C12 C13 . 1.392(4) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 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
    N1 C1 C2 . . 178.1(3) ?
    C7 C2 C3 . . 117.1(3) ?
    C7 C2 C1 . . 122.1(3) ?
    C3 C2 C1 . . 120.8(2) ?
    F1 C3 C4 . . 119.3(3) ?
    F1 C3 C2 . . 119.1(3) ?
    C4 C3 C2 . . 121.6(3) ?
    F2 C4 C3 . . 118.0(3) ?
    F2 C4 C5 . . 120.1(3) ?
    C3 C4 C5 . . 121.9(3) ?
    C6 C5 C4 . . 115.5(3) ?
    C6 C5 C8 . . 122.5(2) ?
    C4 C5 C8 . . 122.0(3) ?
    F3 C6 C7 . . 117.1(3) ?
    F3 C6 C5 . . 119.8(3) ?
    C7 C6 C5 . . 123.0(3) ?
    F4 C7 C6 . . 119.3(3) ?
    F4 C7 C2 . . 119.8(3) ?
    C6 C7 C2 . . 120.9(3) ?
    C9 C8 C13 . . 118.6(3) ?
    C9 C8 C5 . . 121.2(2) ?
    C13 C8 C5 . . 120.3(3) ?
    C10 C9 C8 . . 121.1(3) ?
    C10 C9 H9 . . 119.4 ?
    C8 C9 H9 . . 119.4 ?
    C9 C10 C11 . . 119.2(3) ?
    C9 C10 H10 . . 120.4 ?
    C11 C10 H10 . . 120.4 ?
    C12 C11 C10 . . 121.4(3) ?
    C12 C11 Br1 . . 119.1(2) ?
    C10 C11 Br1 . . 119.5(2) ?
    C11 C12 C13 . . 119.0(3) ?
    C11 C12 H12 . . 120.5 ?
    C13 C12 H12 . . 120.5 ?
    C12 C13 C8 . . 120.7(3) ?
    C12 C13 H13 . . 119.6 ?
    C8 C13 H13 . . 119.6 ?
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
    C7 C2 C3 F1 . . . . 179.9(3) ?
    C1 C2 C3 F1 . . . . -0.5(4) ?
    C7 C2 C3 C4 . . . . 0.1(5) ?
    C1 C2 C3 C4 . . . . 179.7(3) ?
    F1 C3 C4 F2 . . . . 2.6(4) ?
    C2 C3 C4 F2 . . . . -177.5(3) ?
    F1 C3 C4 C5 . . . . -179.5(3) ?
    C2 C3 C4 C5 . . . . 0.3(5) ?
    F2 C4 C5 C6 . . . . 177.3(3) ?
    C3 C4 C5 C6 . . . . -0.5(4) ?
    F2 C4 C5 C8 . . . . -2.6(4) ?
    C3 C4 C5 C8 . . . . 179.6(3) ?
    C4 C5 C6 F3 . . . . 177.6(2) ?
    C8 C5 C6 F3 . . . . -2.4(4) ?
    C4 C5 C6 C7 . . . . 0.2(4) ?
    C8 C5 C6 C7 . . . . -179.8(3) ?
    F3 C6 C7 F4 . . . . 1.8(4) ?
    C5 C6 C7 F4 . . . . 179.3(3) ?
    F3 C6 C7 C2 . . . . -177.3(3) ?
    C5 C6 C7 C2 . . . . 0.2(5) ?
    C3 C2 C7 F4 . . . . -179.4(3) ?
    C1 C2 C7 F4 . . . . 1.0(5) ?
    C3 C2 C7 C6 . . . . -0.3(4) ?
    C1 C2 C7 C6 . . . . -179.9(3) ?
    C6 C5 C8 C9 . . . . 139.2(3) ?
    C4 C5 C8 C9 . . . . -40.8(4) ?
    C6 C5 C8 C13 . . . . -40.4(5) ?
    C4 C5 C8 C13 . . . . 139.6(3) ?
    C13 C8 C9 C10 . . . . -0.3(4) ?
    C5 C8 C9 C10 . . . . -179.9(3) ?
    C8 C9 C10 C11 . . . . 0.3(4) ?
    C9 C10 C11 C12 . . . . -0.2(5) ?
    C9 C10 C11 Br1 . . . . -179.8(2) ?
    C10 C11 C12 C13 . . . . 0.1(5) ?
    Br1 C11 C12 C13 . . . . 179.7(2) ?
    C11 C12 C13 C8 . . . . -0.1(4) ?
    C9 C8 C13 C12 . . . . 0.2(4) ?
    C5 C8 C13 C12 . . . . 179.8(3) ?
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
    C9 H9 F2 . 0.95 2.47 2.882(4) 106.3
    C13 H13 F3 . 0.95 2.45 2.865(3) 106.6
_shelxl_version_number         .000002012
data_Global
_journal_date_recd_electronic     2015-04-16
_journal_date_accepted     2015-04-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      5
_journal_page_first     o347
_journal_page_last     o348
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015007847
_journal_coeditor_code     IM2464
_publ_contact_author_name     'Anke Schwarzer'
_publ_contact_author_address
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_contact_author_email     'anke.schwarzer@chemie.tu-freiberg.de'
_publ_contact_author_fax     '+49 3731 393170'
_publ_contact_author_phone     '+49 3731 393075'
_publ_section_title
;
Crystal structure of 4'-bromo-2,3,5,6-tetrafluorobiphenyl-4-carbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Heckel, Ricarda' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Hulliger, Jürg' .
;
Department of Chemistry and Biochemistry
University of Berne
Freiestrasse 3
CH-3012 Berne
Switzerland
;
    'Schwarzer, Anke' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Weber, Edwin' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_section_synopsis     .
