#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:14:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180383 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/52/7205284.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_7205284
loop_
_publ_author_name
'Collas, Alain'
'De Borger, Roeland'
'Amanova, Tatyana'
'Blockhuys, Frank'
_publ_section_title
;
 Activation and de-activation of fluorine synthons by nitrogen
 substitution in fluorinated aza-distyrylbenzenes
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              702
_journal_paper_doi               10.1039/c0ce00319k
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C20 H6 F10 N2'
_chemical_formula_sum            'C20 H6 F10 N2'
_chemical_formula_weight         464.27
_chemical_melting_point          448
_chemical_name_common
;N,N'-bis(2,3,4,5,6-pentafluorobenzylidene)-1,4-
phenylenediamine
;
_chemical_name_systematic
;
N,N'-bis(2,3,4,5,6-pentafluorobenzylidene)-1,4-phenylenediamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.78(2)
_cell_angle_beta                 102.35(3)
_cell_angle_gamma                96.13(3)
_cell_formula_units_Z            1
_cell_length_a                   5.846(2)
_cell_length_b                   7.929(2)
_cell_length_c                   10.331(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.22
_cell_measurement_theta_min      6.00
_cell_volume                     431.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2612
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        27
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             230.0
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1172P)²+0.0231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                1219
_reflns_number_total             1571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00319K.TXT
_cod_data_source_block           pf345mpa
_cod_original_cell_volume        431.8(2)
_cod_database_code               7205284
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C31 C 0.1777(3) 0.1577(3) 0.5602(2) 0.0469(5) Uani 1 1 d . . .
C32 C 0.2282(4) -0.0061(3) 0.5678(2) 0.0524(5) Uani 1 1 d . . .
H32 H 0.3817 -0.0109 0.6130 0.063 Uiso 1 1 calc R . .
C36 C -0.0527(4) 0.1619(3) 0.4911(2) 0.0504(5) Uani 1 1 d . . .
H36 H -0.0886 0.2708 0.4846 0.060 Uiso 1 1 calc R . .
F2 F 0.4658(2) 0.69214(18) 0.67276(16) 0.0626(4) Uani 1 1 d . . .
F5 F 1.3491(2) 0.6655(2) 0.94843(15) 0.0692(5) Uani 1 1 d . . .
C2 C 0.6816(4) 0.6772(3) 0.7369(2) 0.0468(5) Uani 1 1 d . . .
F6 F 1.0057(2) 0.36729(18) 0.84558(14) 0.0611(4) Uani 1 1 d . . .
C5 C 1.1317(4) 0.6700(3) 0.8784(2) 0.0502(6) Uani 1 1 d . . .
C4 C 1.0840(4) 0.8274(3) 0.8610(2) 0.0520(6) Uani 1 1 d . . .
C11 C 0.5412(4) 0.3466(3) 0.6958(2) 0.0495(5) Uani 1 1 d . . .
H11 H 0.5766 0.2507 0.7242 0.059 Uiso 1 1 calc R . .
F3 F 0.8091(3) 0.98695(19) 0.77885(17) 0.0698(5) Uani 1 1 d . . .
N11 N 0.3443(3) 0.3257(2) 0.6136(2) 0.0559(5) Uani 1 1 d . . .
C6 C 0.9532(4) 0.5169(3) 0.8247(2) 0.0459(5) Uani 1 1 d . . .
C1 C 0.7228(3) 0.5150(3) 0.7513(2) 0.0439(5) Uani 1 1 d . . .
C3 C 0.8571(4) 0.8320(3) 0.7909(2) 0.0508(5) Uani 1 1 d . . .
F4 F 1.2545(3) 0.9771(2) 0.91189(17) 0.0739(5) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 C31 C36 118.9(2) . . ?
C32 C31 N11 125.7(2) . . ?
C36 C31 N11 115.4(2) . . ?
C36 C32 C31 120.5(2) 2_556 . ?
C36 C32 H32 119.7 2_556 . ?
C31 C32 H32 119.7 . . ?
C32 C36 C31 120.6(2) 2_556 . ?
C32 C36 H36 119.7 2_556 . ?
C31 C36 H36 119.7 . . ?
F2 C2 C3 116.51(19) . . ?
F2 C2 C1 121.11(18) . . ?
C3 C2 C1 122.4(2) . . ?
F5 C5 C4 120.1(2) . . ?
F5 C5 C6 120.1(2) . . ?
C4 C5 C6 119.7(2) . . ?
F4 C4 C5 120.7(2) . . ?
F4 C4 C3 119.6(2) . . ?
C5 C4 C3 119.8(2) . . ?
N11 C11 C1 123.5(2) . . ?
N11 C11 H11 118.3 . . ?
C1 C11 H11 118.3 . . ?
C11 N11 C31 121.0(2) . . ?
F6 C6 C5 117.92(19) . . ?
F6 C6 C1 119.77(18) . . ?
C5 C6 C1 122.3(2) . . ?
C2 C1 C6 116.17(19) . . ?
C2 C1 C11 124.3(2) . . ?
C6 C1 C11 119.6(2) . . ?
F3 C3 C2 120.7(2) . . ?
F3 C3 C4 119.61(19) . . ?
C2 C3 C4 119.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C31 C32 1.386(3) . ?
C31 C36 1.393(3) . ?
C31 N11 1.422(3) . ?
C32 C36 1.380(3) 2_556 ?
C32 H32 0.9300 . ?
C36 C32 1.380(3) 2_556 ?
C36 H36 0.9300 . ?
F2 C2 1.331(2) . ?
F5 C5 1.332(3) . ?
C2 C3 1.376(3) . ?
C2 C1 1.384(3) . ?
F6 C6 1.331(3) . ?
C5 C4 1.369(3) . ?
C5 C6 1.377(3) . ?
C4 F4 1.334(2) . ?
C4 C3 1.379(3) . ?
C11 N11 1.233(3) . ?
C11 C1 1.469(3) . ?
C11 H11 0.9300 . ?
F3 C3 1.329(3) . ?
C6 C1 1.393(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C36 C31 C32 C36 -0.5(4) . . . 2_556 ?
N11 C31 C32 C36 -178.32(18) . . . 2_556 ?
C32 C31 C36 C32 0.5(4) . . . 2_556 ?
N11 C31 C36 C32 178.54(17) . . . 2_556 ?
F5 C5 C4 F4 0.9(3) . . . . ?
C6 C5 C4 F4 -179.80(18) . . . . ?
F5 C5 C4 C3 -178.69(18) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C1 C11 N11 C31 178.33(16) . . . . ?
C32 C31 N11 C11 -13.9(4) . . . . ?
C36 C31 N11 C11 168.2(2) . . . . ?
F5 C5 C6 F6 0.3(3) . . . . ?
C4 C5 C6 F6 -179.07(17) . . . . ?
F5 C5 C6 C1 179.70(17) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
F2 C2 C1 C6 -177.79(17) . . . . ?
C3 C2 C1 C6 0.3(3) . . . . ?
F2 C2 C1 C11 1.8(3) . . . . ?
C3 C2 C1 C11 179.87(18) . . . . ?
F6 C6 C1 C2 178.62(17) . . . . ?
C5 C6 C1 C2 -0.8(3) . . . . ?
F6 C6 C1 C11 -1.0(3) . . . . ?
C5 C6 C1 C11 179.56(18) . . . . ?
N11 C11 C1 C2 10.8(4) . . . . ?
N11 C11 C1 C6 -169.6(2) . . . . ?
F2 C2 C3 F3 0.2(3) . . . . ?
C1 C2 C3 F3 -177.90(17) . . . . ?
F2 C2 C3 C4 178.85(18) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
F4 C4 C3 F3 -2.1(3) . . . . ?
C5 C4 C3 F3 177.46(18) . . . . ?
F4 C4 C3 C2 179.27(18) . . . . ?
C5 C4 C3 C2 -1.2(3) . . . . ?
