# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_compound2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common 'Benzaldehyde pentafluoromethylidenehydrazone' _chemical_melting_point 390K _chemical_formula_moiety 'C14 H7 F5 N2' _chemical_formula_sum 'C14 H7 F5 N2' _chemical_formula_weight 298.22 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 Triclinic _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9053(2) _cell_length_b 7.4709(3) _cell_length_c 14.3540(5) _cell_angle_alpha 102.927(2) _cell_angle_beta 92.143(2) _cell_angle_gamma 91.222(2) _cell_volume 616.50(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2294 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9452 _exptl_absorpt_correction_T_max 0.9764 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 4344 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2736 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection "Collect" data collection software, Nonius 1998. _computing_cell_refinement DENZO-SMN _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP and PLUTON _computing_publication_material SHELXL-97 _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^)+(0.0557P)^2^+0.1217P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 2736 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.002 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F17 F 0.67601(13) 0.37547(11) 0.72447(6) 0.0320(2) Uani 1 1 d . . . F21 F -0.03312(13) 0.06178(12) 0.63671(6) 0.0351(2) Uani 1 1 d . . . F20 F -0.11643(13) 0.10058(12) 0.82287(6) 0.0354(2) Uani 1 1 d . . . F18 F 0.59164(14) 0.40608(12) 0.90750(6) 0.0365(2) Uani 1 1 d . . . F19 F 0.19455(15) 0.27199(13) 0.95915(6) 0.0400(3) Uani 1 1 d . . . C3 C 0.0787(2) 0.16784(19) 0.79715(10) 0.0272(3) Uani 1 1 d . . . C2 C 0.1230(2) 0.14964(18) 0.70207(10) 0.0262(3) Uani 1 1 d . . . C5 C 0.4371(2) 0.32289(19) 0.84019(10) 0.0274(3) Uani 1 1 d . . . C1 C 0.3230(2) 0.21878(18) 0.67217(10) 0.0250(3) Uani 1 1 d . . . C10 C 0.5358(2) 0.1983(2) 0.23562(11) 0.0296(3) Uani 1 1 d . . . H10A H 0.396(3) 0.160(2) 0.2599(12) 0.035 Uiso 1 1 d . . . C6 C 0.4779(2) 0.30526(19) 0.74480(10) 0.0253(3) Uani 1 1 d . . . N15 N 0.5134(2) 0.23302(17) 0.43726(8) 0.0317(3) Uani 1 1 d . . . C7 C 0.3551(2) 0.1985(2) 0.56968(10) 0.0278(3) Uani 1 1 d . . . H7A H 0.240(3) 0.130(2) 0.5265(12) 0.033 Uiso 1 1 d . . . C9 C 0.7102(2) 0.27705(18) 0.30112(10) 0.0264(3) Uani 1 1 d . . . N16 N 0.5265(2) 0.27004(17) 0.53839(9) 0.0320(3) Uani 1 1 d . . . C4 C 0.2358(2) 0.2546(2) 0.86646(10) 0.0281(3) Uani 1 1 d . . . C12 C 0.7657(3) 0.2338(2) 0.10565(11) 0.0347(3) Uani 1 1 d . . . H12A H 0.788(3) 0.217(2) 0.0364(13) 0.042 Uiso 1 1 d . . . C8 C 0.6867(3) 0.2988(2) 0.40439(11) 0.0299(3) Uani 1 1 d . . . H8A H 0.811(3) 0.369(2) 0.4472(12) 0.036 Uiso 1 1 d . . . C13 C 0.9390(3) 0.3132(2) 0.17020(11) 0.0333(3) Uani 1 1 d . . . H13A H 1.081(3) 0.356(2) 0.1479(12) 0.040 Uiso 1 1 d . . . C14 C 0.9123(2) 0.3355(2) 0.26771(11) 0.0311(3) Uani 1 1 d . . . H14A H 1.031(3) 0.391(2) 0.3106(13) 0.037 Uiso 1 1 d . . . C11 C 0.5634(3) 0.1761(2) 0.13857(11) 0.0332(3) Uani 1 1 d . . . H11A H 0.449(3) 0.123(2) 0.0960(13) 0.040 Uiso 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 F17 0.0245(4) 0.0385(5) 0.0324(5) 0.0066(4) 0.0046(3) -0.0074(3) F21 0.0285(4) 0.0416(5) 0.0324(5) 0.0040(4) -0.0034(3) -0.0083(4) F20 0.0255(4) 0.0421(5) 0.0399(5) 0.0112(4) 0.0094(4) -0.0055(3) F18 0.0319(5) 0.0466(5) 0.0270(5) 0.0011(4) -0.0026(3) -0.0066(4) F19 0.0416(5) 0.0540(6) 0.0239(5) 0.0069(4) 0.0093(4) -0.0047(4) C3 0.0221(6) 0.0278(7) 0.0333(8) 0.0089(6) 0.0079(6) 0.0003(5) C2 0.0239(7) 0.0254(7) 0.0278(7) 0.0032(6) -0.0013(5) 0.0000(5) C5 0.0261(7) 0.0277(7) 0.0268(7) 0.0029(6) 0.0000(5) 0.0001(5) C1 0.0261(7) 0.0230(7) 0.0261(7) 0.0052(5) 0.0037(5) 0.0020(5) C10 0.0279(7) 0.0294(7) 0.0328(8) 0.0093(6) 0.0051(6) 0.0004(6) C6 0.0211(6) 0.0251(7) 0.0299(7) 0.0060(6) 0.0054(5) -0.0005(5) N15 0.0376(7) 0.0335(7) 0.0241(6) 0.0070(5) 0.0043(5) -0.0028(5) C7 0.0308(7) 0.0275(7) 0.0251(7) 0.0054(6) 0.0026(6) 0.0001(6) C9 0.0285(7) 0.0239(7) 0.0282(7) 0.0080(6) 0.0049(6) 0.0013(5) N16 0.0387(7) 0.0334(7) 0.0240(6) 0.0063(5) 0.0049(5) -0.0017(5) C4 0.0299(7) 0.0321(7) 0.0226(7) 0.0058(6) 0.0061(5) 0.0029(6) C12 0.0392(8) 0.0393(9) 0.0285(8) 0.0123(7) 0.0079(6) 0.0052(7) C8 0.0333(7) 0.0275(7) 0.0287(7) 0.0059(6) 0.0025(6) -0.0001(6) C13 0.0310(8) 0.0364(8) 0.0349(8) 0.0119(7) 0.0092(6) 0.0000(6) C14 0.0289(7) 0.0319(8) 0.0332(8) 0.0088(6) 0.0037(6) -0.0009(6) C11 0.0320(8) 0.0371(8) 0.0306(8) 0.0085(6) -0.0011(6) -0.0001(6) _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 F17 C6 1.3406(15) . ? F21 C2 1.3396(16) . ? F20 C3 1.3443(15) . ? F18 C5 1.3395(16) . ? F19 C4 1.3395(16) . ? C3 C4 1.374(2) . ? C3 C2 1.376(2) . ? C2 C1 1.3992(19) . ? C5 C6 1.377(2) . ? C5 C4 1.3820(19) . ? C1 C6 1.3937(19) . ? C1 C7 1.4647(19) . ? C10 C11 1.382(2) . ? C10 C9 1.395(2) . ? C10 H10A 0.970(17) . ? N15 C8 1.2766(19) . ? N15 N16 1.4145(17) . ? C7 N16 1.2768(18) . ? C7 H7A 0.960(18) . ? C9 C14 1.4000(19) . ? C9 C8 1.467(2) . ? C12 C13 1.384(2) . ? C12 C11 1.396(2) . ? C12 H12A 0.989(18) . ? C8 H8A 0.999(17) . ? C13 C14 1.387(2) . ? C13 H13A 0.980(18) . ? C14 H14A 0.940(18) . ? C11 H11A 0.915(18) . ? 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 F20 C3 C4 119.62(12) . . ? F20 C3 C2 120.60(12) . . ? C4 C3 C2 119.78(12) . . ? F21 C2 C3 117.91(12) . . ? F21 C2 C1 119.62(12) . . ? C3 C2 C1 122.47(12) . . ? F18 C5 C6 120.25(12) . . ? F18 C5 C4 119.95(12) . . ? C6 C5 C4 119.80(12) . . ? C6 C1 C2 115.85(12) . . ? C6 C1 C7 124.86(12) . . ? C2 C1 C7 119.28(12) . . ? C11 C10 C9 120.28(13) . . ? C11 C10 H10A 121.3(10) . . ? C9 C10 H10A 118.5(10) . . ? F17 C6 C5 116.63(12) . . ? F17 C6 C1 121.01(12) . . ? C5 C6 C1 122.36(12) . . ? C8 N15 N16 111.48(12) . . ? N16 C7 C1 122.04(13) . . ? N16 C7 H7A 120.9(10) . . ? C1 C7 H7A 117.0(10) . . ? C10 C9 C14 119.41(13) . . ? C10 C9 C8 121.31(12) . . ? C14 C9 C8 119.28(13) . . ? C7 N16 N15 110.48(12) . . ? F19 C4 C3 120.16(12) . . ? F19 C4 C5 120.12(12) . . ? C3 C4 C5 119.73(12) . . ? C13 C12 C11 120.01(14) . . ? C13 C12 H12A 119.2(10) . . ? C11 C12 H12A 120.8(10) . . ? N15 C8 C9 121.16(13) . . ? N15 C8 H8A 122.1(10) . . ? C9 C8 H8A 116.8(10) . . ? C12 C13 C14 120.16(14) . . ? C12 C13 H13A 120.6(10) . . ? C14 C13 H13A 119.2(10) . . ? C13 C14 C9 120.07(14) . . ? C13 C14 H14A 119.0(11) . . ? C9 C14 H14A 120.9(11) . . ? C10 C11 C12 120.06(14) . . ? C10 C11 H11A 119.9(11) . . ? C12 C11 H11A 120.1(11) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.230 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.045 #######END######## data_compound3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis(Pentafluorophenylmethylidenehydrazone)' _chemical_melting_point 411K _chemical_formula_moiety 'C14 H2 F10 N2' _chemical_formula_sum 'C14 H2 F10 N2' _chemical_formula_weight 388.18 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 2 1/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.65700(10) _cell_length_b 7.9005(2) _cell_length_c 13.1424(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.6800(10) _cell_angle_gamma 90.00 _cell_volume 671.60(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1607 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.51 _exptl_crystal_description lathes _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.920 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9195 _exptl_absorpt_correction_T_max 0.9446 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 3257 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 30.50 _reflns_number_total 1977 _reflns_number_gt 1496 _reflns_threshold_expression >2sigma(I) _computing_data_collection "Collect" data collection software, Nonius 1998. _computing_cell_refinement DENZO-SMN _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP and PLUTON _computing_publication_material SHELXL-97 _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^)+(0.0485P)^2^+0.1857P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 1977 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15637(18) 0.16071(15) 0.07562(9) 0.0247(2) Uani 1 1 d . . . F2 F -0.03177(13) 0.33081(11) -0.06186(6) 0.0370(2) Uani 1 1 d . . . F3 F 0.32348(13) -0.00214(11) 0.22367(6) 0.0430(2) Uani 1 1 d . . . F4 F 0.03426(14) 0.07207(12) 0.32625(6) 0.0416(2) Uani 1 1 d . . . F5 F -0.31923(13) 0.40485(13) 0.04418(6) 0.0437(2) Uani 1 1 d . . . F6 F -0.29031(13) 0.27145(13) 0.23858(6) 0.0428(2) Uani 1 1 d . . . C7 C 0.30618(19) 0.12495(16) 0.01299(10) 0.0277(3) Uani 1 1 d . . . H7 H 0.303(3) 0.193(2) -0.0449(13) 0.039(4) Uiso 1 1 d . . . C8 C 0.0177(2) 0.13300(16) 0.22994(9) 0.0286(3) Uani 1 1 d . . . C9 C 0.16571(19) 0.09609(15) 0.17555(10) 0.0275(3) Uani 1 1 d . . . N10 N 0.43776(17) 0.00502(14) 0.03675(9) 0.0315(3) Uani 1 1 d . . . C11 C -0.14689(19) 0.23664(17) 0.18569(10) 0.0289(3) Uani 1 1 d . . . C12 C -0.16099(19) 0.30451(17) 0.08765(9) 0.0288(3) Uani 1 1 d . . . C13 C -0.01128(19) 0.26569(16) 0.03461(9) 0.0261(3) 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 C1 0.0255(6) 0.0232(5) 0.0263(5) -0.0015(4) 0.0080(4) 0.0009(4) F2 0.0392(4) 0.0479(5) 0.0265(4) 0.0106(3) 0.0133(3) 0.0159(4) F3 0.0466(5) 0.0463(5) 0.0361(5) 0.0137(4) 0.0102(4) 0.0205(4) F4 0.0497(5) 0.0498(5) 0.0274(4) 0.0092(4) 0.0135(4) -0.0016(4) F5 0.0353(4) 0.0624(6) 0.0347(4) 0.0049(4) 0.0109(3) 0.0241(4) F6 0.0357(5) 0.0641(6) 0.0340(4) -0.0033(4) 0.0192(4) 0.0043(4) C7 0.0280(6) 0.0280(6) 0.0286(6) -0.0008(5) 0.0096(5) 0.0026(5) C8 0.0347(6) 0.0293(6) 0.0227(5) 0.0007(5) 0.0083(5) -0.0059(5) C9 0.0297(6) 0.0242(6) 0.0282(6) 0.0016(5) 0.0057(5) 0.0026(5) N10 0.0311(6) 0.0316(5) 0.0355(6) 0.0003(5) 0.0151(5) 0.0062(4) C11 0.0273(6) 0.0359(6) 0.0265(6) -0.0056(5) 0.0121(5) -0.0035(5) C12 0.0251(6) 0.0341(6) 0.0272(6) -0.0012(5) 0.0064(5) 0.0054(5) C13 0.0283(6) 0.0283(6) 0.0225(5) 0.0002(4) 0.0079(4) 0.0023(5) _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 C1 C13 1.3926(17) . ? C1 C9 1.3967(17) . ? C1 C7 1.4629(17) . ? F2 C13 1.3450(14) . ? F3 C9 1.3383(14) . ? F4 C8 1.3341(14) . ? F5 C12 1.3341(14) . ? F6 C11 1.3358(14) . ? C7 N10 1.2780(17) . ? C7 H7 0.930(17) . ? C8 C9 1.3784(18) . ? C8 C11 1.3812(19) . ? N10 N10 1.416(2) 3_655 ? C11 C12 1.3781(18) . ? C12 C13 1.3790(17) . ? 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 C13 C1 C9 115.78(11) . . ? C13 C1 C7 119.20(11) . . ? C9 C1 C7 125.02(11) . . ? N10 C7 C1 121.65(12) . . ? N10 C7 H7 120.7(10) . . ? C1 C7 H7 117.6(10) . . ? F4 C8 C9 120.45(12) . . ? F4 C8 C11 119.52(11) . . ? C9 C8 C11 120.02(11) . . ? F3 C9 C8 117.06(11) . . ? F3 C9 C1 120.78(11) . . ? C8 C9 C1 122.14(12) . . ? C7 N10 N10 110.65(13) . 3_655 ? F6 C11 C12 120.49(12) . . ? F6 C11 C8 119.76(11) . . ? C12 C11 C8 119.75(11) . . ? F5 C12 C11 120.26(11) . . ? F5 C12 C13 120.50(11) . . ? C11 C12 C13 119.24(11) . . ? F2 C13 C12 117.84(11) . . ? F2 C13 C1 119.07(11) . . ? C12 C13 C1 123.07(11) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.236 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.048 ########END########## data_compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 Complex of Benzalazine : bis(Pentafluorophenylmethylidenehydrazone)' _chemical_melting_point 391K _chemical_formula_moiety 'C14 H2 F10 N2 . C14 H12 N2' _chemical_formula_sum 'C14 H2 F10 N2 . C14 H12 N2' _chemical_formula_weight 596.43 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2820(2) _cell_length_b 7.9073(2) _cell_length_c 11.9305(4) _cell_angle_alpha 93.052(2) _cell_angle_beta 93.590(2) _cell_angle_gamma 113.3100(10) _cell_volume 627.37(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2210 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9544 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 4453 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2836 _reflns_number_gt 1819 _reflns_threshold_expression >2sigma(I) _computing_data_collection "Collect" data collection software, Nonius 1998. _computing_cell_refinement DENZO-SMN _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP and PLUTON _computing_publication_material SHELXL-97 _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^)+(0.0362P)^2^+0.5000P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 2836 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.6085(2) 0.5480(2) 0.39763(12) 0.0421(4) Uani 1 1 d . . . F2 F 0.3051(2) 0.4290(3) 0.02804(13) 0.0491(5) Uani 1 1 d . . . F4 F 0.3057(3) -0.0637(2) 0.22549(13) 0.0479(5) Uani 1 1 d . . . F6 F 0.5132(3) 0.6723(2) 0.20745(14) 0.0507(5) Uani 1 1 d . . . F9 F 0.2103(3) 0.0632(3) 0.03926(13) 0.0565(5) Uani 1 1 d . . . N3 N 0.4668(3) 0.0086(3) 0.44437(16) 0.0297(5) Uani 1 1 d . . . C8 C 0.3591(4) 0.1194(3) 0.2262(2) 0.0295(5) Uani 1 1 d . . . C11 C 0.5081(4) 0.4235(3) 0.31046(19) 0.0287(5) Uani 1 1 d . . . C13 C 0.4587(3) 0.2368(3) 0.32116(18) 0.0252(5) Uani 1 1 d . . . C14 C 0.4603(4) 0.4898(3) 0.2136(2) 0.0324(6) Uani 1 1 d . . . C15 C 0.5111(4) 0.1781(3) 0.42872(19) 0.0269(5) Uani 1 1 d . . . H15A H 0.586(4) 0.278(4) 0.486(2) 0.032 Uiso 1 1 d . . . C19 C 0.3583(4) 0.3683(4) 0.1226(2) 0.0346(6) Uani 1 1 d . . . C21 C 0.3089(4) 0.1829(4) 0.1287(2) 0.0350(6) Uani 1 1 d . . . N5 N 1.0137(3) 0.0842(3) 0.47705(17) 0.0331(5) Uani 1 1 d . . . C7 C 0.8666(4) 0.3286(4) 0.1394(2) 0.0348(6) Uani 1 1 d . . . H7A H 0.808(4) 0.305(4) 0.060(2) 0.042 Uiso 1 1 d . . . C10 C 0.9552(4) 0.5074(4) 0.1895(2) 0.0361(6) Uani 1 1 d . . . H10A H 0.959(4) 0.609(4) 0.145(2) 0.043 Uiso 1 1 d . . . C12 C 0.9393(4) 0.2136(3) 0.31309(19) 0.0281(5) Uani 1 1 d . . . C16 C 1.0286(4) 0.3948(4) 0.3624(2) 0.0305(6) Uani 1 1 d . . . H16A H 1.088(4) 0.415(4) 0.439(2) 0.037 Uiso 1 1 d . . . C17 C 1.0355(4) 0.5407(4) 0.3009(2) 0.0357(6) Uani 1 1 d . . . H17A H 1.099(4) 0.664(4) 0.337(2) 0.043 Uiso 1 1 d . . . C18 C 0.9301(4) 0.0576(3) 0.3763(2) 0.0299(6) Uani 1 1 d . . . H18A H 0.854(4) -0.072(4) 0.340(2) 0.036 Uiso 1 1 d . . . C20 C 0.8570(4) 0.1814(4) 0.2007(2) 0.0315(6) Uani 1 1 d . . . H20A H 0.798(4) 0.061(4) 0.169(2) 0.038 Uiso 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 F1 0.0596(11) 0.0301(8) 0.0363(8) 0.0031(6) 0.0016(7) 0.0179(8) F2 0.0431(10) 0.0755(12) 0.0386(9) 0.0335(8) 0.0068(7) 0.0303(9) F4 0.0673(12) 0.0289(9) 0.0382(9) 0.0038(7) -0.0084(8) 0.0114(8) F6 0.0673(12) 0.0377(9) 0.0574(10) 0.0239(8) 0.0125(9) 0.0286(9) F9 0.0607(12) 0.0637(12) 0.0308(8) 0.0022(8) -0.0133(8) 0.0125(9) N3 0.0336(12) 0.0330(12) 0.0250(10) 0.0104(8) 0.0011(8) 0.0153(10) C8 0.0302(13) 0.0299(14) 0.0274(12) 0.0071(10) 0.0023(10) 0.0104(11) C11 0.0323(14) 0.0312(14) 0.0266(12) 0.0063(10) 0.0052(10) 0.0160(11) C13 0.0267(13) 0.0290(13) 0.0235(11) 0.0089(9) 0.0053(9) 0.0137(10) C14 0.0341(14) 0.0327(14) 0.0389(14) 0.0186(11) 0.0106(11) 0.0192(12) C15 0.0295(13) 0.0296(14) 0.0239(12) 0.0064(10) 0.0019(10) 0.0139(11) C19 0.0303(14) 0.0521(17) 0.0292(13) 0.0229(12) 0.0068(10) 0.0218(13) C21 0.0300(14) 0.0472(17) 0.0251(12) 0.0054(11) -0.0019(10) 0.0129(12) N5 0.0373(13) 0.0309(12) 0.0322(11) 0.0105(9) 0.0016(9) 0.0140(10) C7 0.0336(15) 0.0478(17) 0.0287(13) 0.0116(11) 0.0047(11) 0.0210(13) C10 0.0370(15) 0.0417(16) 0.0362(14) 0.0184(12) 0.0068(11) 0.0204(13) C12 0.0260(13) 0.0325(14) 0.0293(12) 0.0086(10) 0.0051(10) 0.0143(11) C16 0.0321(14) 0.0345(15) 0.0280(13) 0.0080(10) 0.0040(10) 0.0158(11) C17 0.0396(15) 0.0300(14) 0.0384(14) 0.0082(11) 0.0026(11) 0.0142(12) C18 0.0316(14) 0.0283(14) 0.0303(13) 0.0058(10) 0.0044(10) 0.0119(11) C20 0.0314(14) 0.0371(15) 0.0281(13) 0.0048(11) 0.0032(10) 0.0158(12) _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 F1 C11 1.346(3) . ? F2 C19 1.343(3) . ? F4 C8 1.342(3) . ? F6 C14 1.345(3) . ? F9 C21 1.344(3) . ? N3 C15 1.276(3) . ? N3 N3 1.416(4) 2_656 ? C8 C21 1.376(3) . ? C8 C13 1.387(3) . ? C11 C14 1.375(3) . ? C11 C13 1.390(3) . ? C13 C15 1.466(3) . ? C14 C19 1.369(4) . ? C15 H15A 0.98(3) . ? C19 C21 1.372(4) . ? N5 C18 1.281(3) . ? N5 N5 1.412(4) 2_756 ? C7 C10 1.383(4) . ? C7 C20 1.388(4) . ? C7 H7A 1.00(3) . ? C10 C17 1.386(4) . ? C10 H10A 0.97(3) . ? C12 C16 1.395(4) . ? C12 C20 1.401(3) . ? C12 C18 1.461(3) . ? C16 C17 1.387(3) . ? C16 H16A 0.96(3) . ? C17 H17A 0.96(3) . ? C18 H18A 1.01(3) . ? C20 H20A 0.93(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 C15 N3 N3 110.4(2) . 2_656 ? F4 C8 C21 116.6(2) . . ? F4 C8 C13 121.1(2) . . ? C21 C8 C13 122.3(2) . . ? F1 C11 C14 117.3(2) . . ? F1 C11 C13 119.6(2) . . ? C14 C11 C13 123.1(2) . . ? C8 C13 C11 115.5(2) . . ? C8 C13 C15 125.2(2) . . ? C11 C13 C15 119.3(2) . . ? F6 C14 C19 120.0(2) . . ? F6 C14 C11 120.6(2) . . ? C19 C14 C11 119.4(2) . . ? N3 C15 C13 122.3(2) . . ? N3 C15 H15A 122.4(15) . . ? C13 C15 H15A 115.3(15) . . ? F2 C19 C14 120.6(2) . . ? F2 C19 C21 119.8(2) . . ? C14 C19 C21 119.6(2) . . ? F9 C21 C19 119.8(2) . . ? F9 C21 C8 120.1(2) . . ? C19 C21 C8 120.1(2) . . ? C18 N5 N5 111.7(3) . 2_756 ? C10 C7 C20 120.1(2) . . ? C10 C7 H7A 119.8(16) . . ? C20 C7 H7A 120.1(16) . . ? C7 C10 C17 120.2(2) . . ? C7 C10 H10A 118.9(17) . . ? C17 C10 H10A 120.9(17) . . ? C16 C12 C20 119.1(2) . . ? C16 C12 C18 121.3(2) . . ? C20 C12 C18 119.6(2) . . ? C17 C16 C12 120.3(2) . . ? C17 C16 H16A 121.5(16) . . ? C12 C16 H16A 118.2(16) . . ? C10 C17 C16 120.1(3) . . ? C10 C17 H17A 121.4(17) . . ? C16 C17 H17A 118.5(17) . . ? N5 C18 C12 120.7(2) . . ? N5 C18 H18A 120.2(15) . . ? C12 C18 H18A 119.0(15) . . ? C7 C20 C12 120.1(3) . . ? C7 C20 H20A 121.5(17) . . ? C12 C20 H20A 118.3(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.204 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.055 ######## END OF FILE #########