##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
#                                                                            #
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data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-11-05
_journal_date_accepted     2010-11-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3177
_journal_page_last     o3177
_journal_paper_category     QO
_journal_coeditor_code     KP2288
_publ_contact_author_name     'von Eschwege, Karel G.'
_publ_contact_author_address
;
Department of Chemistry
University of the Free State
P.O. Box 339
Bloemfontein
9300
South Africa
;
_publ_contact_author_email     veschwkg@ufs.ac.za
_publ_contact_author_fax     '+27-51-444 6384'
_publ_contact_author_phone     '+27-51-401 2923'
_publ_section_title
;
Low-temperature redetermination of 1,3-bis(pentafluorophenyl)triazene
;
loop_
    _publ_author_name
    _publ_author_address
    'von Eschwege, Karel G.'
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein 9300
South Africa
;
    'Kuhn, Annemarie'
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein 9300
South Africa
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
1,3-bis(pentafluorophenyl)triazene
;
_chemical_formula_moiety     'C12 H F10 N3'
_chemical_formula_sum     'C12 H F10 N3'
_chemical_formula_iupac     'C12 H F10 N3'
_chemical_formula_weight     377.16
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     9.9930(8)
_cell_length_b     9.4850(8)
_cell_length_c     12.9200(11)
_cell_angle_alpha     90
_cell_angle_beta     95.585(2)
_cell_angle_gamma     90
_cell_volume     1218.79(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2521
_cell_measurement_theta_min     3.46
_cell_measurement_theta_max     28.11
_cell_measurement_temperature     100(2)
_exptl_crystal_description     cuboid
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     2.055
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     0.234
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker; 2004)
;
_exptl_absorpt_correction_T_min     0.9332
_exptl_absorpt_correction_T_max     0.9658
_exptl_special_details
;
The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD
diffractometer using an exposure time of 10 s/frame. A total of 1126 frames
were collected with a frame width of 0.5° covering up to θ = 28.33° with
98.8% completeness accomplished.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K Kappa CCD
;
_diffrn_measurement_method     φ
_diffrn_detector_area_resol_mean     8.4
_diffrn_reflns_number     12525
_diffrn_reflns_av_R_equivalents     0.0385
_diffrn_reflns_theta_min     2.67
_diffrn_reflns_theta_max     28.33
_diffrn_reflns_theta_full     28.33
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 >
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     3013
_reflns_number_gt     2177
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0588
_refine_ls_R_factor_gt     0.0385
_refine_ls_wR_factor_ref     0.1068
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     3013
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0438P)²+0.6444P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.358
_refine_diff_density_min     -0.314
_refine_ls_extinction_method     none
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 0 '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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    N N1 0.32054(15) -0.00606(18) 0.51342(13) 0.0176(4) Uani d . 1 . .
    N N2 0.29181(15) 0.01759(18) 0.41693(13) 0.0170(4) Uani d . 1 . .
    N N3 0.39984(15) 0.04639(18) 0.36826(13) 0.0187(4) Uani d . 1 . .
    H H3 0.4793 0.0554 0.4034 0.022 Uiso calc R 1 . .
    C C1 0.38491(18) 0.0620(2) 0.26046(15) 0.0161(4) Uani d . 1 . .
    C C2 0.28659(18) -0.0055(2) 0.19428(16) 0.0170(4) Uani d . 1 . .
    C C3 0.27844(18) 0.0129(2) 0.08793(16) 0.0183(4) Uani d . 1 . .
    C C4 0.37001(19) 0.0977(2) 0.04420(16) 0.0198(4) Uani d . 1 . .
    C C5 0.46978(19) 0.1626(2) 0.10765(16) 0.0199(4) Uani d . 1 . .
    C C6 0.47531(18) 0.1467(2) 0.21357(16) 0.0184(4) Uani d . 1 . .
    C C7 0.20622(17) -0.0486(2) 0.56306(15) 0.0156(4) Uani d . 1 . .
    C C8 0.20040(18) -0.0106(2) 0.66629(16) 0.0178(4) Uani d . 1 . .
    C C9 0.09951(19) -0.0571(2) 0.72416(15) 0.0190(4) Uani d . 1 . .
    C C10 0.00216(18) -0.1471(2) 0.67859(16) 0.0187(4) Uani d . 1 . .
    C C11 0.00446(18) -0.1863(2) 0.57591(16) 0.0174(4) Uani d . 1 . .
    C C12 0.10529(18) -0.1381(2) 0.51888(15) 0.0165(4) Uani d . 1 . .
    F F2 0.19834(11) -0.09374(13) 0.23200(9) 0.0218(3) Uani d . 1 . .
    F F3 0.18284(12) -0.05460(13) 0.02754(9) 0.0254(3) Uani d . 1 . .
    F F4 0.36352(12) 0.11346(14) -0.05941(9) 0.0272(3) Uani d . 1 . .
    F F5 0.56138(12) 0.24230(14) 0.06517(10) 0.0283(3) Uani d . 1 . .
    F F6 0.57237(11) 0.21376(13) 0.27471(9) 0.0246(3) Uani d . 1 . .
    F F8 0.29674(11) 0.07433(13) 0.71246(9) 0.0241(3) Uani d . 1 . .
    F F9 0.09641(12) -0.01701(14) 0.82274(9) 0.0269(3) Uani d . 1 . .
    F F10 -0.09396(11) -0.19674(13) 0.73422(10) 0.0243(3) Uani d . 1 . .
    F F11 -0.09111(11) -0.27180(13) 0.53101(10) 0.0245(3) Uani d . 1 . .
    F F12 0.10472(11) -0.18344(13) 0.42082(9) 0.0218(3) 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
    N1 0.0153(7) 0.0214(9) 0.0163(9) 0.0000(6) 0.0024(6) -0.0012(7)
    N2 0.0160(7) 0.0181(9) 0.0172(9) 0.0000(6) 0.0031(6) -0.0005(7)
    N3 0.0142(7) 0.0247(10) 0.0172(9) -0.0037(7) 0.0009(6) 0.0012(7)
    C1 0.0152(8) 0.0164(10) 0.0167(10) 0.0014(7) 0.0017(7) 0.0008(8)
    C2 0.0158(8) 0.0147(10) 0.0209(11) 0.0001(7) 0.0035(7) 0.0003(8)
    C3 0.0173(9) 0.0182(10) 0.0190(11) 0.0016(8) -0.0006(8) -0.0006(8)
    C4 0.0244(10) 0.0200(11) 0.0155(10) 0.0055(8) 0.0040(8) 0.0026(8)
    C5 0.0193(9) 0.0177(11) 0.0236(11) 0.0004(8) 0.0070(8) 0.0035(9)
    C6 0.0150(8) 0.0167(10) 0.0230(11) -0.0002(7) -0.0003(8) -0.0013(8)
    C7 0.0138(8) 0.0171(10) 0.0159(10) 0.0027(7) 0.0014(7) 0.0014(8)
    C8 0.0144(8) 0.0186(11) 0.0199(11) 0.0000(7) -0.0003(7) -0.0018(8)
    C9 0.0210(9) 0.0226(11) 0.0134(10) 0.0053(8) 0.0023(8) 0.0014(8)
    C10 0.0163(9) 0.0192(11) 0.0215(11) 0.0035(8) 0.0060(8) 0.0069(8)
    C11 0.0155(8) 0.0152(10) 0.0211(11) -0.0005(7) -0.0009(7) 0.0004(8)
    C12 0.0176(9) 0.0187(10) 0.0130(10) 0.0025(7) 0.0004(7) -0.0002(8)
    F2 0.0208(5) 0.0244(7) 0.0203(6) -0.0077(5) 0.0023(5) 0.0023(5)
    F3 0.0293(6) 0.0275(7) 0.0183(7) -0.0069(5) -0.0036(5) -0.0011(5)
    F4 0.0334(7) 0.0318(8) 0.0171(7) 0.0016(6) 0.0055(5) 0.0032(5)
    F5 0.0265(6) 0.0308(7) 0.0292(7) -0.0082(5) 0.0106(5) 0.0064(6)
    F6 0.0197(5) 0.0285(7) 0.0252(7) -0.0087(5) -0.0005(5) -0.0005(5)
    F8 0.0226(6) 0.0298(7) 0.0195(7) -0.0071(5) 0.0004(5) -0.0053(5)
    F9 0.0304(6) 0.0342(8) 0.0168(6) -0.0011(5) 0.0060(5) -0.0033(5)
    F10 0.0212(6) 0.0270(7) 0.0260(7) -0.0008(5) 0.0098(5) 0.0048(5)
    F11 0.0198(5) 0.0260(7) 0.0274(7) -0.0088(5) -0.0002(5) -0.0008(5)
    F12 0.0241(6) 0.0249(7) 0.0162(6) -0.0046(5) 0.0018(5) -0.0029(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
    N1 N2 . 1.272(2) ?
    N1 C7 . 1.422(2) ?
    N2 N3 . 1.330(2) ?
    N3 C1 . 1.394(2) ?
    N3 H3 . 0.88 ?
    C1 C6 . 1.391(3) ?
    C1 C2 . 1.394(3) ?
    C2 F2 . 1.341(2) ?
    C2 C3 . 1.380(3) ?
    C3 F3 . 1.336(2) ?
    C3 C4 . 1.380(3) ?
    C4 F4 . 1.342(2) ?
    C4 C5 . 1.373(3) ?
    C5 F5 . 1.345(2) ?
    C5 C6 . 1.373(3) ?
    C6 F6 . 1.349(2) ?
    C7 C8 . 1.388(3) ?
    C7 C12 . 1.397(3) ?
    C8 F8 . 1.349(2) ?
    C8 C9 . 1.385(3) ?
    C9 F9 . 1.332(2) ?
    C9 C10 . 1.382(3) ?
    C10 F10 . 1.340(2) ?
    C10 C11 . 1.380(3) ?
    C11 F11 . 1.341(2) ?
    C11 C12 . 1.383(3) ?
    C12 F12 . 1.337(2) ?
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
    N2 N1 C7 . . 112.19(15) ?
    N1 N2 N3 . . 112.56(15) ?
    N2 N3 C1 . . 118.78(15) ?
    N2 N3 H3 . . 120.6 ?
    C1 N3 H3 . . 120.6 ?
    C6 C1 C2 . . 116.55(18) ?
    C6 C1 N3 . . 119.05(17) ?
    C2 C1 N3 . . 124.38(17) ?
    F2 C2 C3 . . 117.62(17) ?
    F2 C2 C1 . . 120.85(18) ?
    C3 C2 C1 . . 121.51(18) ?
    F3 C3 C2 . . 119.36(17) ?
    F3 C3 C4 . . 120.34(18) ?
    C2 C3 C4 . . 120.28(18) ?
    F4 C4 C5 . . 120.47(18) ?
    F4 C4 C3 . . 120.24(18) ?
    C5 C4 C3 . . 119.27(19) ?
    F5 C5 C6 . . 120.39(18) ?
    F5 C5 C4 . . 119.46(19) ?
    C6 C5 C4 . . 120.14(18) ?
    F6 C6 C5 . . 119.25(17) ?
    F6 C6 C1 . . 118.53(18) ?
    C5 C6 C1 . . 122.21(18) ?
    C8 C7 C12 . . 117.02(17) ?
    C8 C7 N1 . . 118.04(17) ?
    C12 C7 N1 . . 124.61(18) ?
    F8 C8 C9 . . 118.51(18) ?
    F8 C8 C7 . . 119.02(17) ?
    C9 C8 C7 . . 122.46(18) ?
    F9 C9 C10 . . 120.19(17) ?
    F9 C9 C8 . . 120.73(18) ?
    C10 C9 C8 . . 119.08(18) ?
    F10 C10 C11 . . 120.04(18) ?
    F10 C10 C9 . . 120.00(18) ?
    C11 C10 C9 . . 119.95(17) ?
    F11 C11 C10 . . 120.08(17) ?
    F11 C11 C12 . . 119.65(18) ?
    C10 C11 C12 . . 120.28(18) ?
    F12 C12 C11 . . 117.55(17) ?
    F12 C12 C7 . . 121.24(17) ?
    C11 C12 C7 . . 121.18(18) ?
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 N1 N2 N3 . . . . -174.92(16) ?
    N1 N2 N3 C1 . . . . 174.28(17) ?
    N2 N3 C1 C6 . . . . 152.97(18) ?
    N2 N3 C1 C2 . . . . -29.0(3) ?
    C6 C1 C2 F2 . . . . 177.31(17) ?
    N3 C1 C2 F2 . . . . -0.7(3) ?
    C6 C1 C2 C3 . . . . -1.0(3) ?
    N3 C1 C2 C3 . . . . -179.05(18) ?
    F2 C2 C3 F3 . . . . 1.3(3) ?
    C1 C2 C3 F3 . . . . 179.65(17) ?
    F2 C2 C3 C4 . . . . -177.26(17) ?
    C1 C2 C3 C4 . . . . 1.1(3) ?
    F3 C3 C4 F4 . . . . 0.2(3) ?
    C2 C3 C4 F4 . . . . 178.76(17) ?
    F3 C3 C4 C5 . . . . -178.06(18) ?
    C2 C3 C4 C5 . . . . 0.5(3) ?
    F4 C4 C5 F5 . . . . -0.1(3) ?
    C3 C4 C5 F5 . . . . 178.22(18) ?
    F4 C4 C5 C6 . . . . 179.63(18) ?
    C3 C4 C5 C6 . . . . -2.1(3) ?
    F5 C5 C6 F6 . . . . 1.1(3) ?
    C4 C5 C6 F6 . . . . -178.58(18) ?
    F5 C5 C6 C1 . . . . -178.10(18) ?
    C4 C5 C6 C1 . . . . 2.2(3) ?
    C2 C1 C6 F6 . . . . -179.85(17) ?
    N3 C1 C6 F6 . . . . -1.7(3) ?
    C2 C1 C6 C5 . . . . -0.6(3) ?
    N3 C1 C6 C5 . . . . 177.51(18) ?
    N2 N1 C7 C8 . . . . -147.83(18) ?
    N2 N1 C7 C12 . . . . 38.9(3) ?
    C12 C7 C8 F8 . . . . 179.22(17) ?
    N1 C7 C8 F8 . . . . 5.4(3) ?
    C12 C7 C8 C9 . . . . -0.5(3) ?
    N1 C7 C8 C9 . . . . -174.24(18) ?
    F8 C8 C9 F9 . . . . 1.1(3) ?
    C7 C8 C9 F9 . . . . -179.21(18) ?
    F8 C8 C9 C10 . . . . -178.35(17) ?
    C7 C8 C9 C10 . . . . 1.3(3) ?
    F9 C9 C10 F10 . . . . -1.5(3) ?
    C8 C9 C10 F10 . . . . 177.96(17) ?
    F9 C9 C10 C11 . . . . 178.85(17) ?
    C8 C9 C10 C11 . . . . -1.7(3) ?
    F10 C10 C11 F11 . . . . 1.4(3) ?
    C9 C10 C11 F11 . . . . -178.93(17) ?
    F10 C10 C11 C12 . . . . -178.43(17) ?
    C9 C10 C11 C12 . . . . 1.2(3) ?
    F11 C11 C12 F12 . . . . -2.0(3) ?
    C10 C11 C12 F12 . . . . 177.86(17) ?
    F11 C11 C12 C7 . . . . 179.80(17) ?
    C10 C11 C12 C7 . . . . -0.3(3) ?
    C8 C7 C12 F12 . . . . -178.17(17) ?
    N1 C7 C12 F12 . . . . -4.9(3) ?
    C8 C7 C12 C11 . . . . 0.0(3) ?
    N1 C7 C12 C11 . . . . 173.28(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
    N3 H3 N1 3_656 0.88 2.23 3.076(2) 162.2
