 
data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
(E)-4-fluoro-N-(3,4,5-trifluorobenzylidene)aniline
; 
_chemical_name_common            
(E)-4-fluoro-N-(3,4,5-trifluorobenzylidene)aniline
_chemical_melting_point           ?
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum 
 'C13 H7 F4 N' 
_chemical_formula_weight          253.20 
 
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' 
 
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                    11.8955(3) 
_cell_length_b                    7.1235(2) 
_cell_length_c                    25.8183(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  101.6930(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      2142.38(9) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used    18258
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
 
_exptl_crystal_description       Fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max           0.21 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.13 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.570 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1024 
_exptl_absorpt_coefficient_mu     0.142 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9709 
_exptl_absorpt_correction_T_max   0.9818 
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details 
; 
 ?
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean  '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             26821 
_diffrn_reflns_av_R_equivalents   0.0653 
_diffrn_reflns_av_sigmaI/netI     0.0632 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -33 
_diffrn_reflns_limit_l_max        33 
_diffrn_reflns_theta_min          3.22 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              4901 
_reflns_number_gt                 3353 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction         'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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 > 2sigma(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. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0569P)²+0.9569P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4901 
_refine_ls_number_parameters      325 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0856 
_refine_ls_R_factor_gt            0.0530 
_refine_ls_wR_factor_ref          0.1422 
_refine_ls_wR_factor_gt           0.1220 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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 
F111 F 0.81968(12) 0.9084(2) 0.18297(5) 0.0406(3) Uani 1 1 d . . . 
F106 F 1.29277(11) 0.7638(2) 0.59174(5) 0.0436(4) Uani 1 1 d . . . 
F211 F 0.27713(12) 0.5063(2) 0.89494(5) 0.0450(4) Uani 1 1 d . . . 
F105 F 1.12749(12) 0.64817(19) 0.64249(5) 0.0419(3) Uani 1 1 d . . . 
F204 F 0.70006(11) 0.4186(2) 0.56874(5) 0.0460(4) Uani 1 1 d . . . 
F205 F 0.55754(12) 0.2514(2) 0.48767(5) 0.0419(4) Uani 1 1 d . . . 
F104 F 0.90843(12) 0.6237(2) 0.59039(5) 0.0464(4) Uani 1 1 d . . . 
F206 F 0.33922(12) 0.1708(2) 0.49501(5) 0.0457(4) Uani 1 1 d . . . 
N101 N 0.91424(15) 0.8023(2) 0.39976(6) 0.0285(4) Uani 1 1 d . . . 
C208 C 0.41902(17) 0.4646(3) 0.76266(8) 0.0263(4) Uani 1 1 d . . . 
N201 N 0.47078(15) 0.4409(2) 0.71791(7) 0.0278(4) Uani 1 1 d . . . 
C203 C 0.55768(18) 0.4180(3) 0.62055(8) 0.0298(5) Uani 1 1 d . . . 
H203 H 0.6089 0.4749 0.6493 0.036 Uiso 1 1 calc R . . 
C201 C 0.40419(19) 0.4047(3) 0.67392(8) 0.0289(5) Uani 1 1 d . . . 
H201 H 0.3240 0.3970 0.6729 0.035 Uiso 1 1 calc R . . 
C109 C 0.96674(19) 0.7547(3) 0.31268(8) 0.0302(5) Uani 1 1 d . . . 
H109 H 1.0326 0.6845 0.3286 0.036 Uiso 1 1 calc R . . 
C213 C 0.47832(19) 0.3974(3) 0.81139(8) 0.0300(5) Uani 1 1 d . . . 
H213 H 0.5521 0.3428 0.8139 0.036 Uiso 1 1 calc R . . 
C107 C 1.15724(18) 0.7922(3) 0.51097(8) 0.0302(5) Uani 1 1 d . . . 
H107 H 1.2156 0.8317 0.4931 0.036 Uiso 1 1 calc R . . 
C207 C 0.37037(19) 0.2923(3) 0.58189(8) 0.0304(5) Uani 1 1 d . . . 
H207 H 0.2933 0.2649 0.5841 0.036 Uiso 1 1 calc R . . 
C202 C 0.44545(18) 0.3740(3) 0.62459(8) 0.0279(5) Uani 1 1 d . . . 
C110 C 0.94143(19) 0.7814(3) 0.25808(8) 0.0322(5) Uani 1 1 d . . . 
H110 H 0.9896 0.7307 0.2364 0.039 Uiso 1 1 calc R . . 
C101 C 1.01637(18) 0.8152(3) 0.42666(8) 0.0280(5) Uani 1 1 d . . . 
H101 H 1.0764 0.8506 0.4094 0.034 Uiso 1 1 calc R . . 
C102 C 1.04366(18) 0.7767(3) 0.48380(8) 0.0265(4) Uani 1 1 d . . . 
C112 C 0.77105(19) 0.9566(3) 0.26586(8) 0.0311(5) Uani 1 1 d . . . 
H112 H 0.7043 1.0239 0.2495 0.037 Uiso 1 1 calc R . . 
C212 C 0.4310(2) 0.4095(3) 0.85604(8) 0.0321(5) Uani 1 1 d . . . 
H212 H 0.4705 0.3616 0.8891 0.038 Uiso 1 1 calc R . . 
C209 C 0.31335(18) 0.5520(3) 0.75997(8) 0.0311(5) Uani 1 1 d . . . 
H209 H 0.2735 0.6019 0.7273 0.037 Uiso 1 1 calc R . . 
C108 C 0.89532(18) 0.8313(3) 0.34398(8) 0.0274(4) Uani 1 1 d . . . 
C103 C 0.95833(19) 0.7211(3) 0.51071(8) 0.0294(5) Uani 1 1 d . . . 
H103 H 0.8806 0.7118 0.4926 0.035 Uiso 1 1 calc R . . 
C106 C 1.18338(18) 0.7496(3) 0.56400(8) 0.0305(5) Uani 1 1 d . . . 
C111 C 0.84517(19) 0.8826(3) 0.23640(8) 0.0303(5) Uani 1 1 d . . . 
C113 C 0.79758(18) 0.9291(3) 0.32015(8) 0.0293(5) Uani 1 1 d . . . 
H113 H 0.7480 0.9781 0.3414 0.035 Uiso 1 1 calc R . . 
C204 C 0.59254(19) 0.3776(3) 0.57424(9) 0.0323(5) Uani 1 1 d . . . 
C210 C 0.26570(19) 0.5669(3) 0.80447(8) 0.0353(5) Uani 1 1 d . . . 
H210 H 0.1938 0.6271 0.8028 0.042 Uiso 1 1 calc R . . 
C205 C 0.52049(19) 0.2932(3) 0.53219(8) 0.0310(5) Uani 1 1 d . . . 
C211 C 0.3251(2) 0.4926(3) 0.85117(8) 0.0325(5) Uani 1 1 d . . . 
C105 C 1.1006(2) 0.6922(3) 0.59059(8) 0.0304(5) Uani 1 1 d . . . 
C206 C 0.40947(19) 0.2522(3) 0.53664(8) 0.0311(5) Uani 1 1 d . . . 
C104 C 0.98820(19) 0.6801(3) 0.56365(8) 0.0310(5) Uani 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
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 
F111 C111 1.363(2) . ? 
F106 C106 1.356(2) . ? 
F211 C211 1.369(2) . ? 
F105 C105 1.350(2) . ? 
F204 C204 1.347(2) . ? 
F205 C205 1.345(2) . ? 
F104 C104 1.343(2) . ? 
F206 C206 1.351(2) . ? 
N101 C101 1.275(3) . ? 
N101 C108 1.427(3) . ? 
C208 C209 1.392(3) . ? 
C208 C213 1.396(3) . ? 
C208 N201 1.425(2) . ? 
N201 C201 1.272(3) . ? 
C203 C204 1.373(3) . ? 
C203 C202 1.396(3) . ? 
C203 H203 0.9500 . ? 
C201 C202 1.471(3) . ? 
C201 H201 0.9500 . ? 
C109 C110 1.394(3) . ? 
C109 C108 1.397(3) . ? 
C109 H109 0.9500 . ? 
C213 C212 1.384(3) . ? 
C213 H213 0.9500 . ? 
C107 C106 1.375(3) . ? 
C107 C102 1.395(3) . ? 
C107 H107 0.9500 . ? 
C207 C206 1.372(3) . ? 
C207 C202 1.398(3) . ? 
C207 H207 0.9500 . ? 
C110 C111 1.373(3) . ? 
C110 H110 0.9500 . ? 
C101 C102 1.471(3) . ? 
C101 H101 0.9500 . ? 
C102 C103 1.398(3) . ? 
C112 C111 1.380(3) . ? 
C112 C113 1.387(3) . ? 
C112 H112 0.9500 . ? 
C212 C211 1.374(3) . ? 
C212 H212 0.9500 . ? 
C209 C210 1.384(3) . ? 
C209 H209 0.9500 . ? 
C108 C113 1.388(3) . ? 
C103 C104 1.372(3) . ? 
C103 H103 0.9500 . ? 
C106 C105 1.372(3) . ? 
C113 H113 0.9500 . ? 
C204 C205 1.377(3) . ? 
C210 C211 1.374(3) . ? 
C210 H210 0.9500 . ? 
C205 C206 1.380(3) . ? 
C105 C104 1.379(3) . ? 
 
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 
C101 N101 C108 118.52(18) . . ? 
C209 C208 C213 118.98(19) . . ? 
C209 C208 N201 123.14(18) . . ? 
C213 C208 N201 117.88(18) . . ? 
C201 N201 C208 117.04(18) . . ? 
C204 C203 C202 118.7(2) . . ? 
C204 C203 H203 120.7 . . ? 
C202 C203 H203 120.7 . . ? 
N201 C201 C202 123.11(19) . . ? 
N201 C201 H201 118.4 . . ? 
C202 C201 H201 118.4 . . ? 
C110 C109 C108 120.0(2) . . ? 
C110 C109 H109 120.0 . . ? 
C108 C109 H109 120.0 . . ? 
C212 C213 C208 120.8(2) . . ? 
C212 C213 H213 119.6 . . ? 
C208 C213 H213 119.6 . . ? 
C106 C107 C102 118.9(2) . . ? 
C106 C107 H107 120.5 . . ? 
C102 C107 H107 120.5 . . ? 
C206 C207 C202 119.1(2) . . ? 
C206 C207 H207 120.5 . . ? 
C202 C207 H207 120.5 . . ? 
C203 C202 C207 120.18(19) . . ? 
C203 C202 C201 121.56(19) . . ? 
C207 C202 C201 118.22(19) . . ? 
C111 C110 C109 118.4(2) . . ? 
C111 C110 H110 120.8 . . ? 
C109 C110 H110 120.8 . . ? 
N101 C101 C102 121.69(19) . . ? 
N101 C101 H101 119.2 . . ? 
C102 C101 H101 119.2 . . ? 
C107 C102 C103 119.95(19) . . ? 
C107 C102 C101 118.95(19) . . ? 
C103 C102 C101 121.09(19) . . ? 
C111 C112 C113 117.6(2) . . ? 
C111 C112 H112 121.2 . . ? 
C113 C112 H112 121.2 . . ? 
C211 C212 C213 118.1(2) . . ? 
C211 C212 H212 121.0 . . ? 
C213 C212 H212 121.0 . . ? 
C210 C209 C208 120.7(2) . . ? 
C210 C209 H209 119.7 . . ? 
C208 C209 H209 119.7 . . ? 
C113 C108 C109 119.53(19) . . ? 
C113 C108 N101 117.82(18) . . ? 
C109 C108 N101 122.51(19) . . ? 
C104 C103 C102 119.2(2) . . ? 
C104 C103 H103 120.4 . . ? 
C102 C103 H103 120.4 . . ? 
F106 C106 C105 117.87(18) . . ? 
F106 C106 C107 120.56(19) . . ? 
C105 C106 C107 121.6(2) . . ? 
F111 C111 C110 118.65(19) . . ? 
F111 C111 C112 118.03(19) . . ? 
C110 C111 C112 123.30(19) . . ? 
C112 C113 C108 121.2(2) . . ? 
C112 C113 H113 119.4 . . ? 
C108 C113 H113 119.4 . . ? 
F204 C204 C203 120.46(19) . . ? 
F204 C204 C205 117.65(19) . . ? 
C203 C204 C205 121.9(2) . . ? 
C211 C210 C209 118.3(2) . . ? 
C211 C210 H210 120.8 . . ? 
C209 C210 H210 120.8 . . ? 
F205 C205 C204 120.7(2) . . ? 
F205 C205 C206 120.6(2) . . ? 
C204 C205 C206 118.68(19) . . ? 
F211 C211 C210 118.1(2) . . ? 
F211 C211 C212 118.86(19) . . ? 
C210 C211 C212 123.02(19) . . ? 
F105 C105 C106 121.0(2) . . ? 
F105 C105 C104 119.81(19) . . ? 
C106 C105 C104 119.14(19) . . ? 
F206 C206 C207 120.3(2) . . ? 
F206 C206 C205 118.21(19) . . ? 
C207 C206 C205 121.5(2) . . ? 
F104 C104 C103 120.6(2) . . ? 
F104 C104 C105 118.22(19) . . ? 
C103 C104 C105 121.2(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.248 
_refine_diff_density_min   -0.317 
_refine_diff_density_rms    0.063 
