#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228454.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228454
loop_
_publ_author_name
'von Eschwege, Karel G.'
'Kuhn, Annemarie'
_publ_section_title
;
 Low-temperature redetermination of 1,3-bis(pentafluorophenyl)triazene
;
_journal_coeditor_code           KP2288
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3177
_journal_paper_doi               10.1107/S1600536810045447
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H F10 N3'
_chemical_formula_moiety         'C12 H F10 N3'
_chemical_formula_sum            'C12 H F10 N3'
_chemical_formula_weight         377.16
_chemical_name_systematic
;
1,3-bis(pentafluorophenyl)triazene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.585(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9930(8)
_cell_length_b                   9.4850(8)
_cell_length_c                   12.9200(11)
_cell_measurement_reflns_used    2521
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      3.46
_cell_volume                     1218.79(18)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.4
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K Kappa CCD
;
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12525
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker; 2004)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.6444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                2177
_reflns_number_total             3013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            kp2288.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228454
_cod_database_fobs_code          2228454
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'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656373
