# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Blockhuys, Frank' _publ_contact_author_email Frank.Blockhuys@ua.ac.be _publ_section_title ; Activation and de-activation of fluorine synthons by nitrogen substitution in fluorinated aza-distyrylbenzenes ; loop_ _publ_author_name A.Collas 'R.De Borger' T.Amanova F.Blockhuys # Attachment '- compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 781116' #TrackingRef '- compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-(p-phenylenedimethylidyne)bis[2,3,4,5,6-pentafluoroaniline] ; _chemical_name_common ;N,N'-(p-phenylenedimethylidyne)bis(2,3,4,5,6- pentafluoroaniline) ; _chemical_melting_point 458 _chemical_formula_moiety 'C20 H6 F10 N2' _chemical_formula_sum 'C20 H6 F10 N2' _chemical_formula_weight 464.27 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 '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 4.871(2) _cell_length_b 6.3980(10) _cell_length_c 28.420(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.57(2) _cell_angle_gamma 90.00 _cell_volume 879.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.36 _cell_measurement_theta_max 10.23 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_detector_area_resol_mean ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -1 _diffrn_reflns_number 3389 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1582 _reflns_number_gt 1108 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2496P] where P=(Fo^2^+2Fc^2^)/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 1582 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _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 F6 F -0.1775(3) -0.0179(2) -0.16615(4) 0.0811(5) Uani 1 1 d . . . F2 F -0.2844(3) 0.61526(19) -0.08651(5) 0.0762(4) Uani 1 1 d . . . F5 F -0.6098(3) 0.0791(3) -0.22839(5) 0.1024(6) Uani 1 1 d . . . N1 N 0.0108(3) 0.2624(2) -0.08970(5) 0.0467(4) Uani 1 1 d . . . C1 C -0.2187(4) 0.2943(3) -0.12351(6) 0.0448(4) Uani 1 1 d . . . F3 F -0.7179(3) 0.7105(2) -0.14931(6) 0.1010(5) Uani 1 1 d . . . C9 C 0.2862(4) 0.0425(3) -0.03536(6) 0.0432(4) Uani 1 1 d . . . F4 F -0.8843(3) 0.4423(3) -0.22086(5) 0.1019(6) Uani 1 1 d . . . C8 C 0.0548(4) 0.0829(3) -0.07181(7) 0.0474(5) Uani 1 1 d . . . H8 H -0.0629 -0.0264 -0.0821 0.057 Uiso 1 1 calc R . . C4 C -0.6680(4) 0.3958(4) -0.18952(8) 0.0664(6) Uani 1 1 d . . . C11 C 0.3311(4) -0.1599(3) -0.01835(7) 0.0502(5) Uani 1 1 d . . . H11 H 0.2169 -0.2678 -0.0307 0.060 Uiso 1 1 calc R . . C6 C -0.3108(4) 0.1613(3) -0.16053(7) 0.0544(5) Uani 1 1 d . . . C10 C 0.4574(4) 0.2014(3) -0.01653(6) 0.0481(5) Uani 1 1 d . . . H10 H 0.4290 0.3373 -0.0276 0.058 Uiso 1 1 calc R . . C2 C -0.3605(4) 0.4812(3) -0.12179(7) 0.0520(5) Uani 1 1 d . . . C5 C -0.5301(4) 0.2110(4) -0.19322(7) 0.0635(6) Uani 1 1 d . . . C3 C -0.5822(4) 0.5314(4) -0.15376(8) 0.0649(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F6 0.0878(10) 0.0825(9) 0.0669(8) -0.0243(7) -0.0181(7) 0.0311(8) F2 0.0873(9) 0.0543(7) 0.0832(9) -0.0086(7) -0.0070(7) 0.0113(7) F5 0.0871(10) 0.1475(15) 0.0636(9) -0.0304(9) -0.0297(7) 0.0076(10) N1 0.0434(8) 0.0504(9) 0.0435(8) 0.0039(7) -0.0065(7) 0.0055(7) C1 0.0399(9) 0.0524(11) 0.0404(10) 0.0067(8) -0.0027(8) 0.0027(8) F3 0.0904(11) 0.0881(10) 0.1210(13) 0.0211(9) -0.0033(9) 0.0479(9) C9 0.0413(9) 0.0495(10) 0.0375(9) 0.0005(8) -0.0017(8) 0.0067(8) F4 0.0584(8) 0.1620(16) 0.0781(9) 0.0332(10) -0.0232(7) 0.0259(9) C8 0.0439(10) 0.0505(11) 0.0450(10) -0.0003(8) -0.0073(8) 0.0025(8) C4 0.0428(11) 0.1000(18) 0.0532(12) 0.0233(13) -0.0076(9) 0.0093(12) C11 0.0494(10) 0.0457(10) 0.0522(11) -0.0001(9) -0.0077(9) -0.0014(9) C6 0.0503(11) 0.0661(13) 0.0447(10) -0.0022(10) -0.0038(9) 0.0111(10) C10 0.0507(10) 0.0431(10) 0.0473(10) 0.0035(8) -0.0077(8) 0.0062(8) C2 0.0528(11) 0.0503(11) 0.0515(11) 0.0057(9) 0.0002(9) 0.0032(9) C5 0.0521(12) 0.0914(17) 0.0436(11) -0.0028(11) -0.0096(9) 0.0019(12) C3 0.0534(12) 0.0684(14) 0.0721(15) 0.0227(12) 0.0040(11) 0.0218(11) _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 F6 C6 1.336(2) . ? F2 C2 1.339(2) . ? F5 C5 1.331(3) . ? N1 C8 1.264(2) . ? N1 C1 1.403(2) . ? C1 C2 1.384(3) . ? C1 C6 1.388(3) . ? F3 C3 1.336(2) . ? C9 C10 1.383(2) . ? C9 C11 1.391(3) . ? C9 C8 1.464(2) . ? F4 C4 1.333(2) . ? C8 H8 0.9300 . ? C4 C3 1.365(3) . ? C4 C5 1.370(3) . ? C11 C10 1.371(3) 3_655 ? C11 H11 0.9300 . ? C6 C5 1.370(3) . ? C10 C11 1.371(3) 3_655 ? C10 H10 0.9300 . ? C2 C3 1.368(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 C8 N1 C1 119.54(16) . . ? C2 C1 C6 115.92(17) . . ? C2 C1 N1 117.61(17) . . ? C6 C1 N1 126.38(17) . . ? C10 C9 C11 119.08(16) . . ? C10 C9 C8 121.70(17) . . ? C11 C9 C8 119.20(17) . . ? N1 C8 C9 121.76(17) . . ? N1 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? F4 C4 C3 120.4(2) . . ? F4 C4 C5 119.9(2) . . ? C3 C4 C5 119.66(18) . . ? C10 C11 C9 120.43(17) 3_655 . ? C10 C11 H11 119.8 3_655 . ? C9 C11 H11 119.8 . . ? F6 C6 C5 118.02(19) . . ? F6 C6 C1 119.83(17) . . ? C5 C6 C1 122.1(2) . . ? C11 C10 C9 120.48(17) 3_655 . ? C11 C10 H10 119.8 3_655 . ? C9 C10 H10 119.8 . . ? F2 C2 C3 118.47(18) . . ? F2 C2 C1 118.89(16) . . ? C3 C2 C1 122.60(19) . . ? F5 C5 C4 120.07(19) . . ? F5 C5 C6 120.0(2) . . ? C4 C5 C6 120.0(2) . . ? F3 C3 C4 120.2(2) . . ? F3 C3 C2 120.0(2) . . ? C4 C3 C2 119.8(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 141.59(19) . . . . ? C8 N1 C1 C6 -42.1(3) . . . . ? C1 N1 C8 C9 -178.09(16) . . . . ? C10 C9 C8 N1 4.2(3) . . . . ? C11 C9 C8 N1 -177.40(19) . . . . ? C10 C9 C11 C10 -0.1(3) . . . 3_655 ? C8 C9 C11 C10 -178.56(18) . . . 3_655 ? C2 C1 C6 F6 176.84(18) . . . . ? N1 C1 C6 F6 0.5(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? N1 C1 C6 C5 -176.78(19) . . . . ? C11 C9 C10 C11 0.1(3) . . . 3_655 ? C8 C9 C10 C11 178.51(18) . . . 3_655 ? C6 C1 C2 F2 179.02(18) . . . . ? N1 C1 C2 F2 -4.3(3) . . . . ? C6 C1 C2 C3 1.5(3) . . . . ? N1 C1 C2 C3 178.13(19) . . . . ? F4 C4 C5 F5 0.8(3) . . . . ? C3 C4 C5 F5 -179.0(2) . . . . ? F4 C4 C5 C6 -178.8(2) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? F6 C6 C5 F5 2.1(3) . . . . ? C1 C6 C5 F5 179.4(2) . . . . ? F6 C6 C5 C4 -178.3(2) . . . . ? C1 C6 C5 C4 -0.9(3) . . . . ? F4 C4 C3 F3 1.3(3) . . . . ? C5 C4 C3 F3 -178.9(2) . . . . ? F4 C4 C3 C2 179.8(2) . . . . ? C5 C4 C3 C2 -0.4(3) . . . . ? F2 C2 C3 F3 -0.2(3) . . . . ? C1 C2 C3 F3 177.40(18) . . . . ? F2 C2 C3 C4 -178.64(19) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.141 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.032 # Attachment '- compound4.cif' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 781117' #TrackingRef '- compound4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2,3,4,5,6-pentafluorostyryl)-2,5-pyrazine ; _chemical_name_common Bis(2,3,4,5,6-pentafluorostyryl)-2,5-pyrazine _chemical_melting_point 477 _chemical_formula_moiety 'C20 H6 F10 N2' _chemical_formula_sum 'C20 H6 F10 N2' _chemical_formula_weight 464.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 6.223(2) _cell_length_b 5.9070(10) _cell_length_c 24.427(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.80(3) _cell_angle_gamma 90.00 _cell_volume 872.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.03 _cell_measurement_theta_max 13.01 _exptl_crystal_description plates _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 19 _diffrn_reflns_number 3326 _diffrn_reflns_av_R_equivalents 0.0941 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1598 _reflns_number_gt 778 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0827P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 1598 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1477 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1738 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _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 N1 N 0.1194(5) 0.8030(5) 0.01881(13) 0.0467(8) Uani 1 1 d . . . F4 F 1.4161(4) 0.8233(5) 0.22107(11) 0.0855(9) Uani 1 1 d . . . F5 F 1.1503(4) 1.1723(5) 0.23291(10) 0.0818(9) Uani 1 1 d . . . F6 F 0.7384(4) 1.1937(4) 0.17173(10) 0.0637(8) Uani 1 1 d . . . C1 C 0.7741(6) 0.8487(6) 0.12505(15) 0.0435(10) Uani 1 1 d . . . F2 F 0.8399(4) 0.4963(4) 0.08722(10) 0.0676(8) Uani 1 1 d . . . C9 C 0.2016(6) 1.0081(6) 0.03511(14) 0.0410(9) Uani 1 1 d . . . C3 C 1.1256(7) 0.6582(7) 0.15343(18) 0.0568(11) Uani 1 1 d . . . C7 C 0.5521(6) 0.8496(6) 0.08833(15) 0.0446(10) Uani 1 1 d . . . H7 H 0.4976 0.7101 0.0736 0.053 Uiso 1 1 calc R . . C6 C 0.8635(6) 1.0167(7) 0.16371(15) 0.0481(10) Uani 1 1 d . . . C5 C 1.0743(7) 1.0094(7) 0.19578(15) 0.0539(11) Uani 1 1 d . . . C2 C 0.9148(7) 0.6680(6) 0.12288(16) 0.0479(10) Uani 1 1 d . . . C10 C -0.0783(7) 0.7977(6) -0.01597(16) 0.0491(11) Uani 1 1 d . . . H10 H -0.1388 0.6575 -0.0284 0.059 Uiso 1 1 calc R . . C4 C 1.2084(7) 0.8287(8) 0.19053(17) 0.0583(12) Uani 1 1 d . . . F3 F 1.2571(4) 0.4845(5) 0.14803(12) 0.0826(9) Uani 1 1 d . . . C8 C 0.4188(6) 1.0245(6) 0.07341(15) 0.0469(10) Uani 1 1 d . . . H8 H 0.4667 1.1657 0.0882 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.047(2) 0.0294(17) 0.0563(19) -0.0038(15) -0.0027(16) -0.0003(16) F4 0.0499(16) 0.119(2) 0.0779(17) 0.0133(17) -0.0042(12) 0.0089(16) F5 0.0678(18) 0.092(2) 0.0750(17) -0.0265(15) -0.0033(14) -0.0111(15) F6 0.0628(16) 0.0510(14) 0.0714(15) -0.0166(12) 0.0047(12) 0.0075(12) C1 0.045(2) 0.038(2) 0.048(2) 0.0052(18) 0.0118(18) -0.0031(18) F2 0.0710(17) 0.0445(14) 0.0850(17) -0.0098(13) 0.0140(12) 0.0078(13) C9 0.048(2) 0.0314(19) 0.0421(18) -0.0024(17) 0.0075(17) 0.0040(18) C3 0.047(3) 0.057(3) 0.067(3) 0.013(2) 0.015(2) 0.016(2) C7 0.043(2) 0.036(2) 0.052(2) -0.0003(17) 0.0067(19) -0.0044(18) C6 0.045(2) 0.052(3) 0.048(2) 0.003(2) 0.0120(19) 0.004(2) C5 0.045(3) 0.067(3) 0.046(2) -0.006(2) 0.0043(19) -0.009(2) C2 0.052(3) 0.038(2) 0.054(2) 0.0035(19) 0.013(2) 0.0017(19) C10 0.052(3) 0.027(2) 0.064(3) -0.0034(18) 0.004(2) -0.0038(19) C4 0.037(2) 0.079(3) 0.056(3) 0.015(2) 0.006(2) 0.004(2) F3 0.0668(17) 0.0760(19) 0.103(2) 0.0140(16) 0.0161(15) 0.0305(15) C8 0.047(2) 0.034(2) 0.055(2) -0.0039(18) 0.0032(18) -0.0006(18) _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 N1 C10 1.318(4) . ? N1 C9 1.338(4) . ? F4 C4 1.330(4) . ? F5 C5 1.330(4) . ? F6 C6 1.345(4) . ? C1 C2 1.390(5) . ? C1 C6 1.391(5) . ? C1 C7 1.457(5) . ? F2 C2 1.346(4) . ? C9 C10 1.397(5) 3_575 ? C9 C8 1.452(5) . ? C3 F3 1.338(4) . ? C3 C2 1.347(6) . ? C3 C4 1.370(6) . ? C7 C8 1.320(5) . ? C7 H7 0.9300 . ? C6 C5 1.359(5) . ? C5 C4 1.379(6) . ? C10 C9 1.397(5) 3_575 ? C10 H10 0.9300 . ? C8 H8 0.9300 . ? 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 C10 N1 C9 116.4(3) . . ? C2 C1 C6 114.9(4) . . ? C2 C1 C7 119.5(3) . . ? C6 C1 C7 125.6(3) . . ? N1 C9 C10 120.2(3) . 3_575 ? N1 C9 C8 118.9(3) . . ? C10 C9 C8 120.9(3) 3_575 . ? F3 C3 C2 121.0(4) . . ? F3 C3 C4 119.1(4) . . ? C2 C3 C4 119.8(4) . . ? C8 C7 C1 127.8(3) . . ? C8 C7 H7 116.1 . . ? C1 C7 H7 116.1 . . ? F6 C6 C5 117.0(4) . . ? F6 C6 C1 120.1(3) . . ? C5 C6 C1 122.9(4) . . ? F5 C5 C6 120.5(4) . . ? F5 C5 C4 119.9(4) . . ? C6 C5 C4 119.6(4) . . ? F2 C2 C3 117.9(3) . . ? F2 C2 C1 118.7(3) . . ? C3 C2 C1 123.4(4) . . ? N1 C10 C9 123.3(3) . 3_575 ? N1 C10 H10 118.3 . . ? C9 C10 H10 118.3 3_575 . ? F4 C4 C3 121.0(4) . . ? F4 C4 C5 119.7(4) . . ? C3 C4 C5 119.3(4) . . ? C7 C8 C9 123.5(3) . . ? C7 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C9 C10 0.8(6) . . . 3_575 ? C10 N1 C9 C8 -180.0(3) . . . . ? C2 C1 C7 C8 -160.6(4) . . . . ? C6 C1 C7 C8 19.5(6) . . . . ? C2 C1 C6 F6 -176.3(3) . . . . ? C7 C1 C6 F6 3.6(6) . . . . ? C2 C1 C6 C5 2.0(5) . . . . ? C7 C1 C6 C5 -178.1(4) . . . . ? F6 C6 C5 F5 -0.4(5) . . . . ? C1 C6 C5 F5 -178.7(4) . . . . ? F6 C6 C5 C4 178.2(3) . . . . ? C1 C6 C5 C4 -0.1(6) . . . . ? F3 C3 C2 F2 0.7(5) . . . . ? C4 C3 C2 F2 -179.6(4) . . . . ? F3 C3 C2 C1 -177.2(4) . . . . ? C4 C3 C2 C1 2.5(6) . . . . ? C6 C1 C2 F2 178.9(3) . . . . ? C7 C1 C2 F2 -1.0(5) . . . . ? C6 C1 C2 C3 -3.2(5) . . . . ? C7 C1 C2 C3 176.9(4) . . . . ? C9 N1 C10 C9 -0.8(6) . . . 3_575 ? F3 C3 C4 F4 -0.1(6) . . . . ? C2 C3 C4 F4 -179.9(3) . . . . ? F3 C3 C4 C5 179.3(3) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? F5 C5 C4 F4 -2.7(6) . . . . ? C6 C5 C4 F4 178.7(4) . . . . ? F5 C5 C4 C3 177.9(4) . . . . ? C6 C5 C4 C3 -0.7(6) . . . . ? C1 C7 C8 C9 178.2(4) . . . . ? N1 C9 C8 C7 8.0(6) . . . . ? C10 C9 C8 C7 -172.8(4) 3_575 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.274 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.073 # Attachment '- compound3.cif' data_pf345mpa _database_code_depnum_ccdc_archive 'CCDC 781118' #TrackingRef '- compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2,3,4,5,6-pentafluorobenzylidene)-1,4-phenylenediamine ; _chemical_name_common ;N,N'-bis(2,3,4,5,6-pentafluorobenzylidene)-1,4- phenylenediamine ; _chemical_melting_point 448 _chemical_formula_moiety 'C20 H6 F10 N2' _chemical_formula_sum 'C20 H6 F10 N2' _chemical_formula_weight 464.27 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.846(2) _cell_length_b 7.929(2) _cell_length_c 10.331(3) _cell_angle_alpha 109.78(2) _cell_angle_beta 102.35(3) _cell_angle_gamma 96.13(3) _cell_volume 431.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 14.22 _exptl_crystal_description prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 230.0 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_detector_area_resol_mean ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 27 _diffrn_reflns_number 2612 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1571 _reflns_number_gt 1219 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.1172P)^2^+0.0231P] where P=(Fo^2^+2Fc^2^)/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 1571 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _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 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C31 0.0373(10) 0.0458(11) 0.0509(11) 0.0148(9) 0.0071(8) 0.0008(8) C32 0.0353(10) 0.0526(11) 0.0618(12) 0.0198(9) 0.0025(9) 0.0040(9) C36 0.0403(11) 0.0469(12) 0.0599(12) 0.0197(9) 0.0071(9) 0.0050(9) F2 0.0416(7) 0.0603(8) 0.0840(9) 0.0325(7) 0.0042(6) 0.0092(6) F5 0.0371(7) 0.0810(10) 0.0740(9) 0.0229(7) -0.0025(6) 0.0021(6) C2 0.0361(10) 0.0509(11) 0.0506(11) 0.0170(9) 0.0102(8) 0.0059(9) F6 0.0510(8) 0.0570(8) 0.0720(9) 0.0266(6) 0.0047(6) 0.0114(6) C5 0.0338(10) 0.0614(13) 0.0473(11) 0.0148(9) 0.0064(8) 0.0027(9) C4 0.0430(11) 0.0485(12) 0.0525(11) 0.0102(9) 0.0101(9) -0.0064(9) C11 0.0411(10) 0.0434(10) 0.0582(12) 0.0178(9) 0.0065(9) 0.0017(9) F3 0.0687(9) 0.0474(7) 0.0900(10) 0.0273(7) 0.0138(8) 0.0065(7) N11 0.0407(10) 0.0485(10) 0.0694(12) 0.0212(9) 0.0027(8) -0.0012(8) C6 0.0400(11) 0.0471(11) 0.0466(10) 0.0152(8) 0.0086(8) 0.0052(9) C1 0.0362(10) 0.0460(10) 0.0451(10) 0.0141(8) 0.0098(8) 0.0020(8) C3 0.0487(12) 0.0450(11) 0.0561(12) 0.0171(9) 0.0141(9) 0.0038(9) F4 0.0551(8) 0.0597(8) 0.0831(10) 0.0141(7) 0.0050(7) -0.0180(7) _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 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_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_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) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.255 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.072