# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Joerg Sundermeyer' _publ_contact_author_email JSU@STAFF.UNI-MARBURG.DE loop_ _publ_author_name J.Sundermeyer T.Linder data_tlc22 _database_code_depnum_ccdc_archive 'CCDC 715077' _audit_creation_date 2008-03-14T11:01:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H17 N2, C12 F10 N' _chemical_formula_sum 'C21 H17 F10 N3' _chemical_formula_weight 501.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8625(11) _cell_length_b 10.3192(12) _cell_length_c 10.8965(12) _cell_angle_alpha 81.843(13) _cell_angle_beta 80.651(13) _cell_angle_gamma 75.228(13) _cell_volume 1052.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 466(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9413 _exptl_absorpt_correction_T_max 0.9768 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'rotation method' _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_number 10424 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.935 _diffrn_measured_fraction_theta_max 0.924 _reflns_number_total 3839 _reflns_number_gt 3077 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SIR97 (Giacovazzo et al, 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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0613P)^2^+0.0203P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3839 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.196 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_ _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 C1 C 0.37417(12) 0.36725(12) 0.23390(13) 0.0294(3) Uani 1 1 d . . . C2 C 0.46152(13) 0.39797(14) 0.31006(15) 0.0353(3) Uani 1 1 d . . . C3 C 0.50887(14) 0.51484(16) 0.28980(17) 0.0448(4) Uani 1 1 d . . . C4 C 0.46980(16) 0.60964(15) 0.19163(19) 0.0492(4) Uani 1 1 d . . . C5 C 0.38511(16) 0.58428(14) 0.11361(17) 0.0452(4) Uani 1 1 d . . . C6 C 0.34108(14) 0.46553(13) 0.13356(14) 0.0350(3) Uani 1 1 d . . . C7 C 0.21823(12) 0.22652(12) 0.22863(12) 0.0252(3) Uani 1 1 d . . . C8 C 0.20998(14) 0.09689(13) 0.20725(13) 0.0304(3) Uani 1 1 d . . . C9 C 0.08827(16) 0.06737(14) 0.18475(14) 0.0375(3) Uani 1 1 d . . . C10 C -0.03582(15) 0.16574(16) 0.18327(15) 0.0415(4) Uani 1 1 d . . . C11 C -0.03510(14) 0.29344(15) 0.20576(14) 0.0372(3) Uani 1 1 d . . . C12 C 0.08680(13) 0.32133(12) 0.22851(13) 0.0293(3) Uani 1 1 d . . . C13 C 0.23171(12) 0.17838(12) -0.23687(12) 0.0259(3) Uani 1 1 d . . . C14 C 0.38559(13) 0.01244(14) -0.32943(14) 0.0323(3) Uani 1 1 d . . . C15 C 0.32448(14) 0.10096(14) -0.41936(15) 0.0332(3) Uani 1 1 d . . . C16 C 0.36304(16) -0.00350(15) -0.09458(15) 0.0349(3) Uani 1 1 d . . . C17 C 0.14587(17) 0.26219(16) -0.13870(16) 0.0388(3) Uani 1 1 d . . . C18 C 0.13833(15) 0.32033(13) -0.42473(15) 0.0335(3) Uani 1 1 d . . . C19 C -0.01399(15) 0.30822(14) -0.41384(16) 0.0355(3) Uani 1 1 d . . . C20 C -0.03257(15) 0.18284(15) -0.46061(15) 0.0358(3) Uani 1 1 d . . . C21 C -0.18741(19) 0.1891(2) -0.4643(2) 0.0529(4) Uani 1 1 d . . . N1 N 0.34127(11) 0.24343(10) 0.25731(11) 0.0293(3) Uani 1 1 d . . . N2 N 0.32660(10) 0.06187(10) -0.21672(10) 0.0263(2) Uani 1 1 d . . . N3 N 0.22934(10) 0.20389(10) -0.35989(11) 0.0273(2) Uani 1 1 d . . . F1 F 0.50198(9) 0.30821(9) 0.40785(10) 0.0497(3) Uani 1 1 d . . . F2 F 0.59281(10) 0.53727(11) 0.36658(12) 0.0658(3) Uani 1 1 d . . . F3 F 0.51505(12) 0.72472(10) 0.17131(14) 0.0752(4) Uani 1 1 d . . . F4 F 0.34748(12) 0.67435(10) 0.01590(12) 0.0683(3) Uani 1 1 d . . . F5 F 0.26603(9) 0.44305(9) 0.04845(9) 0.0457(2) Uani 1 1 d . . . F6 F 0.32821(9) -0.00388(7) 0.20674(9) 0.0422(2) Uani 1 1 d . . . F7 F 0.09109(11) -0.05811(9) 0.16035(10) 0.0553(3) Uani 1 1 d . . . F8 F -0.15487(11) 0.13705(12) 0.16109(12) 0.0691(3) Uani 1 1 d . . . F9 F -0.15583(9) 0.39090(10) 0.20956(11) 0.0583(3) Uani 1 1 d . . . F10 F 0.07626(8) 0.44643(8) 0.26061(8) 0.0392(2) Uani 1 1 d . . . H1 H 0.3408(17) 0.1021(16) -0.5058(19) 0.042(4) Uiso 1 1 d . . . H2 H 0.4556(17) -0.0687(17) -0.3293(16) 0.043(4) Uiso 1 1 d . . . H3 H 0.058(3) 0.233(3) -0.103(3) 0.097(8) Uiso 1 1 d . . . H4 H 0.126(3) 0.353(3) -0.166(3) 0.094(8) Uiso 1 1 d . . . H5 H 0.195(2) 0.256(2) -0.075(2) 0.069(6) Uiso 1 1 d . . . H6 H 0.2786(17) -0.0262(16) -0.0430(16) 0.039(4) Uiso 1 1 d . . . H7 H 0.3990(17) 0.0551(17) -0.0534(17) 0.044(4) Uiso 1 1 d . . . H8 H 0.438(2) -0.085(2) -0.1065(19) 0.058(5) Uiso 1 1 d . . . H9 H 0.1426(16) 0.4026(17) -0.3901(16) 0.039(4) Uiso 1 1 d . . . H10 H 0.1802(18) 0.3223(17) -0.5107(19) 0.043(4) Uiso 1 1 d . . . H11 H -0.0634(18) 0.3175(17) -0.3230(18) 0.046(4) Uiso 1 1 d . . . H12 H -0.0622(16) 0.3865(17) -0.4606(17) 0.041(4) Uiso 1 1 d . . . H13 H 0.0076(17) 0.1058(18) -0.4042(18) 0.043(4) Uiso 1 1 d . . . H14 H 0.0222(18) 0.1686(17) -0.5406(19) 0.047(5) Uiso 1 1 d . . . H15 H -0.245(2) 0.2002(19) -0.380(2) 0.062(6) Uiso 1 1 d . . . H16 H -0.203(2) 0.111(2) -0.491(2) 0.072(6) Uiso 1 1 d . . . H17 H -0.230(2) 0.270(2) -0.514(2) 0.066(6) 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 C1 0.0270(6) 0.0255(6) 0.0352(9) -0.0074(5) -0.0012(5) -0.0051(5) C2 0.0302(6) 0.0340(7) 0.0429(10) -0.0103(6) -0.0062(6) -0.0057(5) C3 0.0320(7) 0.0430(8) 0.0656(12) -0.0269(8) 0.0006(7) -0.0133(6) C4 0.0406(7) 0.0296(7) 0.0788(14) -0.0166(8) 0.0111(8) -0.0168(6) C5 0.0446(8) 0.0278(7) 0.0578(11) 0.0027(6) 0.0035(7) -0.0091(6) C6 0.0362(7) 0.0304(7) 0.0381(9) -0.0018(6) -0.0024(6) -0.0097(5) C7 0.0320(6) 0.0250(6) 0.0187(7) -0.0004(5) -0.0033(5) -0.0077(5) C8 0.0392(7) 0.0263(6) 0.0256(8) -0.0025(5) -0.0011(5) -0.0100(5) C9 0.0568(9) 0.0368(7) 0.0273(9) -0.0038(6) -0.0020(6) -0.0284(7) C10 0.0423(7) 0.0580(9) 0.0332(9) 0.0035(6) -0.0103(6) -0.0292(7) C11 0.0322(7) 0.0451(8) 0.0331(9) 0.0043(6) -0.0068(5) -0.0101(6) C12 0.0331(6) 0.0276(6) 0.0273(8) -0.0016(5) -0.0044(5) -0.0076(5) C13 0.0295(6) 0.0252(6) 0.0248(8) -0.0021(5) -0.0063(5) -0.0084(5) C14 0.0317(6) 0.0297(7) 0.0327(9) -0.0045(5) -0.0026(5) -0.0023(5) C15 0.0359(7) 0.0366(7) 0.0247(9) -0.0065(5) -0.0011(5) -0.0045(5) C16 0.0387(7) 0.0376(8) 0.0301(9) 0.0061(6) -0.0144(6) -0.0114(6) C17 0.0478(8) 0.0376(8) 0.0294(10) -0.0092(6) -0.0071(6) -0.0030(6) C18 0.0424(7) 0.0278(7) 0.0289(9) 0.0047(5) -0.0109(6) -0.0060(5) C19 0.0377(7) 0.0294(7) 0.0370(10) 0.0013(6) -0.0137(6) -0.0010(5) C20 0.0417(7) 0.0361(8) 0.0294(9) -0.0010(6) -0.0069(6) -0.0089(6) C21 0.0475(9) 0.0541(11) 0.0624(14) -0.0056(9) -0.0159(8) -0.0165(8) N1 0.0310(5) 0.0236(5) 0.0344(7) -0.0015(4) -0.0091(4) -0.0064(4) N2 0.0275(5) 0.0254(5) 0.0264(7) 0.0011(4) -0.0074(4) -0.0071(4) N3 0.0303(5) 0.0265(5) 0.0242(7) -0.0002(4) -0.0060(4) -0.0051(4) F1 0.0514(5) 0.0516(5) 0.0524(7) -0.0073(4) -0.0255(4) -0.0113(4) F2 0.0490(5) 0.0723(7) 0.0931(9) -0.0418(6) -0.0107(5) -0.0264(5) F3 0.0648(6) 0.0371(5) 0.1286(11) -0.0206(6) 0.0123(6) -0.0304(5) F4 0.0785(7) 0.0390(5) 0.0785(9) 0.0218(5) -0.0039(6) -0.0172(5) F5 0.0573(5) 0.0457(5) 0.0370(6) 0.0075(4) -0.0145(4) -0.0186(4) F6 0.0484(5) 0.0242(4) 0.0504(6) -0.0064(3) -0.0006(4) -0.0047(3) F7 0.0843(7) 0.0448(5) 0.0511(7) -0.0103(4) -0.0047(5) -0.0408(5) F8 0.0585(6) 0.0893(8) 0.0788(9) 0.0052(6) -0.0265(5) -0.0493(6) F9 0.0304(4) 0.0621(6) 0.0767(8) 0.0030(5) -0.0135(4) -0.0026(4) F10 0.0375(4) 0.0276(4) 0.0510(6) -0.0105(3) -0.0061(4) -0.0012(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 1.3766(16) . ? C1 C6 1.401(2) . ? C1 C2 1.4062(19) . ? C2 F1 1.3499(18) . ? C2 C3 1.378(2) . ? C3 F2 1.3478(18) . ? C3 C4 1.376(3) . ? C4 F3 1.3498(16) . ? C4 C5 1.376(3) . ? C5 F4 1.344(2) . ? C5 C6 1.379(2) . ? C6 F5 1.3540(17) . ? C7 N1 1.3591(16) . ? C7 C12 1.4110(18) . ? C7 C8 1.4144(17) . ? C8 F6 1.3499(15) . ? C8 C9 1.3772(19) . ? C9 F7 1.3510(16) . ? C9 C10 1.377(2) . ? C10 F8 1.3469(16) . ? C10 C11 1.376(2) . ? C11 F9 1.3476(17) . ? C11 C12 1.3724(19) . ? C12 F10 1.3592(15) . ? C13 N3 1.3318(18) . ? C13 N2 1.3370(16) . ? C13 C17 1.4846(19) . ? C14 C15 1.347(2) . ? C14 N2 1.3789(18) . ? C14 H2 0.940(17) . ? C15 N3 1.3850(17) . ? C15 H1 0.928(19) . ? C16 N2 1.4603(18) . ? C16 H6 0.987(17) . ? C16 H7 0.965(18) . ? C16 H8 0.98(2) . ? C17 H3 0.99(3) . ? C17 H4 0.93(3) . ? C17 H5 0.90(2) . ? C18 N3 1.4709(17) . ? C18 C19 1.5232(19) . ? C18 H9 0.989(17) . ? C18 H10 0.960(19) . ? C19 C20 1.518(2) . ? C19 H11 1.036(19) . ? C19 H12 0.951(17) . ? C20 C21 1.519(2) . ? C20 H13 0.973(18) . ? C20 H14 0.957(19) . ? C21 H15 1.01(2) . ? C21 H16 0.95(2) . ? C21 H17 0.97(2) . ? 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 N1 C1 C6 127.25(12) . . ? N1 C1 C2 118.61(13) . . ? C6 C1 C2 113.87(12) . . ? F1 C2 C3 118.08(13) . . ? F1 C2 C1 118.48(12) . . ? C3 C2 C1 123.45(15) . . ? F2 C3 C4 119.70(14) . . ? F2 C3 C2 120.14(16) . . ? C4 C3 C2 120.15(14) . . ? F3 C4 C3 120.63(16) . . ? F3 C4 C5 120.56(17) . . ? C3 C4 C5 118.81(13) . . ? F4 C5 C4 119.89(14) . . ? F4 C5 C6 119.77(15) . . ? C4 C5 C6 120.33(15) . . ? F5 C6 C5 117.22(14) . . ? F5 C6 C1 119.40(11) . . ? C5 C6 C1 123.34(14) . . ? N1 C7 C12 127.98(11) . . ? N1 C7 C8 119.19(11) . . ? C12 C7 C8 112.52(11) . . ? F6 C8 C9 117.65(11) . . ? F6 C8 C7 118.55(11) . . ? C9 C8 C7 123.79(12) . . ? F7 C9 C10 119.47(13) . . ? F7 C9 C8 119.91(13) . . ? C10 C9 C8 120.60(12) . . ? F8 C10 C11 121.02(14) . . ? F8 C10 C9 120.66(14) . . ? C11 C10 C9 118.32(12) . . ? F9 C11 C12 119.61(13) . . ? F9 C11 C10 119.89(12) . . ? C12 C11 C10 120.47(13) . . ? F10 C12 C11 116.94(12) . . ? F10 C12 C7 118.65(11) . . ? C11 C12 C7 124.27(12) . . ? N3 C13 N2 107.33(11) . . ? N3 C13 C17 127.10(12) . . ? N2 C13 C17 125.56(12) . . ? C15 C14 N2 106.90(12) . . ? C15 C14 H2 134.4(10) . . ? N2 C14 H2 118.7(10) . . ? C14 C15 N3 106.87(13) . . ? C14 C15 H1 130.7(10) . . ? N3 C15 H1 122.4(10) . . ? N2 C16 H6 109.6(10) . . ? N2 C16 H7 110.1(11) . . ? H6 C16 H7 110.2(14) . . ? N2 C16 H8 108.9(12) . . ? H6 C16 H8 110.1(15) . . ? H7 C16 H8 107.8(15) . . ? C13 C17 H3 112.5(15) . . ? C13 C17 H4 112.5(17) . . ? H3 C17 H4 111(2) . . ? C13 C17 H5 110.3(14) . . ? H3 C17 H5 107(2) . . ? H4 C17 H5 103(2) . . ? N3 C18 C19 112.87(11) . . ? N3 C18 H9 108.2(9) . . ? C19 C18 H9 110.8(9) . . ? N3 C18 H10 105.0(10) . . ? C19 C18 H10 110.0(10) . . ? H9 C18 H10 109.8(14) . . ? C20 C19 C18 115.23(12) . . ? C20 C19 H11 110.9(9) . . ? C18 C19 H11 110.4(9) . . ? C20 C19 H12 109.8(10) . . ? C18 C19 H12 105.9(9) . . ? H11 C19 H12 103.9(14) . . ? C19 C20 C21 111.57(13) . . ? C19 C20 H13 107.5(10) . . ? C21 C20 H13 110.2(10) . . ? C19 C20 H14 110.8(10) . . ? C21 C20 H14 111.3(10) . . ? H13 C20 H14 105.3(15) . . ? C20 C21 H15 111.9(11) . . ? C20 C21 H16 113.5(13) . . ? H15 C21 H16 106.1(18) . . ? C20 C21 H17 110.2(12) . . ? H15 C21 H17 102.5(17) . . ? H16 C21 H17 112.0(18) . . ? C7 N1 C1 120.99(11) . . ? C13 N2 C14 109.51(11) . . ? C13 N2 C16 125.56(12) . . ? C14 N2 C16 124.93(11) . . ? C13 N3 C15 109.39(11) . . ? C13 N3 C18 126.32(12) . . ? C15 N3 C18 124.28(13) . . ? 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 N1 C1 C2 F1 -4.18(18) . . . . ? C6 C1 C2 F1 -178.62(12) . . . . ? N1 C1 C2 C3 175.45(13) . . . . ? C6 C1 C2 C3 1.0(2) . . . . ? F1 C2 C3 F2 -0.2(2) . . . . ? C1 C2 C3 F2 -179.79(12) . . . . ? F1 C2 C3 C4 -179.67(13) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? F2 C3 C4 F3 0.2(2) . . . . ? C2 C3 C4 F3 179.69(13) . . . . ? F2 C3 C4 C5 179.40(13) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? F3 C4 C5 F4 0.3(2) . . . . ? C3 C4 C5 F4 -178.91(14) . . . . ? F3 C4 C5 C6 178.92(13) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? F4 C5 C6 F5 3.0(2) . . . . ? C4 C5 C6 F5 -175.63(13) . . . . ? F4 C5 C6 C1 -179.19(13) . . . . ? C4 C5 C6 C1 2.2(2) . . . . ? N1 C1 C6 F5 1.5(2) . . . . ? C2 C1 C6 F5 175.33(11) . . . . ? N1 C1 C6 C5 -176.32(13) . . . . ? C2 C1 C6 C5 -2.5(2) . . . . ? N1 C7 C8 F6 -4.96(19) . . . . ? C12 C7 C8 F6 -179.10(11) . . . . ? N1 C7 C8 C9 176.12(13) . . . . ? C12 C7 C8 C9 2.0(2) . . . . ? F6 C8 C9 F7 -1.5(2) . . . . ? C7 C8 C9 F7 177.39(12) . . . . ? F6 C8 C9 C10 -179.64(12) . . . . ? C7 C8 C9 C10 -0.7(2) . . . . ? F7 C9 C10 F8 1.8(2) . . . . ? C8 C9 C10 F8 179.90(14) . . . . ? F7 C9 C10 C11 -178.61(13) . . . . ? C8 C9 C10 C11 -0.5(2) . . . . ? F8 C10 C11 F9 2.0(2) . . . . ? C9 C10 C11 F9 -177.57(13) . . . . ? F8 C10 C11 C12 179.85(14) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? F9 C11 C12 F10 3.4(2) . . . . ? C10 C11 C12 F10 -174.42(13) . . . . ? F9 C11 C12 C7 179.08(12) . . . . ? C10 C11 C12 C7 1.2(2) . . . . ? N1 C7 C12 F10 -0.2(2) . . . . ? C8 C7 C12 F10 173.35(11) . . . . ? N1 C7 C12 C11 -175.76(14) . . . . ? C8 C7 C12 C11 -2.3(2) . . . . ? N2 C14 C15 N3 0.35(14) . . . . ? N3 C18 C19 C20 -56.70(19) . . . . ? C18 C19 C20 C21 -171.50(14) . . . . ? C12 C7 N1 C1 -31.3(2) . . . . ? C8 C7 N1 C1 155.62(12) . . . . ? C6 C1 N1 C7 -34.6(2) . . . . ? C2 C1 N1 C7 151.75(13) . . . . ? N3 C13 N2 C14 -0.04(13) . . . . ? C17 C13 N2 C14 179.92(12) . . . . ? N3 C13 N2 C16 179.84(11) . . . . ? C17 C13 N2 C16 -0.20(19) . . . . ? C15 C14 N2 C13 -0.20(14) . . . . ? C15 C14 N2 C16 179.92(12) . . . . ? N2 C13 N3 C15 0.26(13) . . . . ? C17 C13 N3 C15 -179.70(13) . . . . ? N2 C13 N3 C18 178.71(11) . . . . ? C17 C13 N3 C18 -1.2(2) . . . . ? C14 C15 N3 C13 -0.38(14) . . . . ? C14 C15 N3 C18 -178.88(11) . . . . ? C19 C18 N3 C13 -75.82(17) . . . . ? C19 C18 N3 C15 102.41(15) . . . . ? # Attachment '[iPiPIM][BPFPA].cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-02-07 at 17:12:14 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : tlgj1 absorb struct ipds2 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_tlgj1 _database_code_depnum_ccdc_archive 'CCDC 715078' _audit_creation_date 2009-02-07T17:12:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H17 F10' _chemical_formula_sum 'C21 H17 F10 N3' _chemical_formula_weight 501.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.1670(16) _cell_length_b 11.0290(10) _cell_length_c 13.6160(14) _cell_angle_alpha 90 _cell_angle_beta 91.0680(10) _cell_angle_gamma 90 _cell_volume 2127.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 8436 _cell_measurement_theta_min 1.495 _cell_measurement_theta_max 27.13 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9401 _exptl_absorpt_correction_T_max 0.9961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 6.67 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_unetI/netI 0.0238 _diffrn_reflns_number 10551 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.76 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2269 _reflns_number_gt 1627 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0632P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0051(8) _refine_ls_number_reflns 2269 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.102 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.208 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_ _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 C1 C -0.07319(10) 0.24852(13) 0.70554(9) 0.0423(3) Uani 1 1 d . . . C2 C -0.06985(12) 0.13814(14) 0.65409(11) 0.0488(4) Uani 1 1 d . . . C3 C -0.14604(14) 0.08924(15) 0.60414(12) 0.0574(4) Uani 1 1 d . . . C4 C -0.23086(13) 0.14860(17) 0.60010(12) 0.0601(5) Uani 1 1 d . . . C5 C -0.23784(11) 0.25846(18) 0.64711(12) 0.0578(4) Uani 1 1 d . . . C6 C -0.16196(11) 0.30490(14) 0.69924(10) 0.0473(4) Uani 1 1 d . . . C10 C 0.20126(12) 0.65296(18) 0.89050(13) 0.0534(4) Uani 1 1 d . . . C11 C 0.05763(15) 0.6663(2) 0.99637(12) 0.0605(4) Uani 1 1 d . . . C12 C 0.09908(11) 0.61844(14) 0.90251(10) 0.0450(4) Uani 1 1 d . . . C13 C 0 0.59177(19) 0.75 0.0393(4) Uani 1 2 d S . . C14 C 0.02619(11) 0.78080(14) 0.79152(11) 0.0469(4) Uani 1 1 d . . . N1 N 0 0.30871(15) 0.75 0.0435(4) Uani 1 2 d S . . N11 N 0.04236(8) 0.66198(10) 0.81671(8) 0.0397(3) Uani 1 1 d . . . F1 F 0.01266(7) 0.07761(8) 0.64917(7) 0.0607(3) Uani 1 1 d . . . F2 F -0.13668(9) -0.01741(9) 0.55630(8) 0.0807(4) Uani 1 1 d . . . F3 F -0.30598(8) 0.10039(12) 0.55110(9) 0.0840(4) Uani 1 1 d . . . F4 F -0.31972(7) 0.32019(13) 0.64361(8) 0.0829(4) Uani 1 1 d . . . F5 F -0.17395(7) 0.41080(9) 0.74780(7) 0.0611(3) Uani 1 1 d . . . H1 H 0 0.508(2) 0.75 0.042(5) Uiso 1 2 d S . . H2 H 0.0510(13) 0.8462(17) 0.8282(13) 0.056(5) Uiso 1 1 d . . . H3 H 0.0918(10) 0.5322(15) 0.9003(10) 0.039(4) Uiso 1 1 d . . . H4 H 0.2081(12) 0.7409(19) 0.8896(12) 0.059(5) Uiso 1 1 d . . . H5 H 0.2257(14) 0.6188(17) 0.8299(15) 0.062(5) Uiso 1 1 d . . . H6 H 0.2360(15) 0.6178(18) 0.9451(16) 0.075(6) Uiso 1 1 d . . . H7 H 0.0638(13) 0.753(2) 1.0014(13) 0.067(5) Uiso 1 1 d . . . H8 H -0.0097(17) 0.6523(18) 1.0003(15) 0.073(6) Uiso 1 1 d . . . H9 H 0.0897(15) 0.6303(19) 1.0530(16) 0.074(6) 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 C1 0.0483(8) 0.0392(7) 0.0394(7) 0.0069(6) -0.0008(6) -0.0024(6) C2 0.0568(9) 0.0415(8) 0.0475(8) 0.0040(6) -0.0112(7) 0.0002(7) C3 0.0751(11) 0.0442(9) 0.0521(9) 0.0078(7) -0.0212(8) -0.0103(8) C4 0.0605(10) 0.0647(11) 0.0543(9) 0.0143(8) -0.0169(8) -0.0196(9) C5 0.0411(8) 0.0783(12) 0.0541(9) 0.0201(9) 0.0012(6) 0.0004(8) C6 0.0506(9) 0.0479(9) 0.0436(7) 0.0058(6) 0.0050(6) 0.0020(7) C10 0.0522(9) 0.0592(11) 0.0483(8) 0.0071(8) -0.0133(7) -0.0058(8) C11 0.0720(12) 0.0689(13) 0.0405(8) -0.0012(8) 0.0007(8) -0.0086(10) C12 0.0526(9) 0.0447(8) 0.0374(7) 0.0032(6) -0.0080(6) -0.0043(7) C13 0.0459(11) 0.0344(11) 0.0373(9) 0 -0.0036(8) 0 C14 0.0494(8) 0.0367(8) 0.0543(8) -0.0028(6) -0.0058(6) -0.0026(6) N1 0.0484(10) 0.0367(9) 0.0453(9) 0 -0.0038(7) 0 N11 0.0430(6) 0.0378(6) 0.0382(6) 0.0003(5) -0.0041(5) -0.0024(5) F1 0.0718(7) 0.0462(5) 0.0634(6) -0.0128(4) -0.0209(5) 0.0135(4) F2 0.1115(9) 0.0490(6) 0.0796(7) -0.0050(5) -0.0480(6) -0.0064(6) F3 0.0713(7) 0.0977(9) 0.0818(7) 0.0195(6) -0.0342(6) -0.0300(6) F4 0.0442(6) 0.1212(10) 0.0834(7) 0.0115(7) -0.0012(5) 0.0114(6) F5 0.0590(6) 0.0640(6) 0.0606(6) -0.0002(4) 0.0074(4) 0.0143(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.3633(16) . ? C1 C6 1.404(2) . ? C1 C2 1.406(2) . ? C2 F1 1.3490(19) . ? C2 C3 1.375(2) . ? C3 F2 1.352(2) . ? C3 C4 1.369(3) . ? C4 F3 1.3542(18) . ? C4 C5 1.375(3) . ? C5 F4 1.345(2) . ? C5 C6 1.376(2) . ? C6 F5 1.3543(18) . ? C10 C12 1.509(2) . ? C10 H4 0.97(2) . ? C10 H5 0.98(2) . ? C10 H6 0.96(2) . ? C11 C12 1.512(2) . ? C11 H7 0.97(2) . ? C11 H8 0.97(2) . ? C11 H9 0.97(2) . ? C12 N11 1.4854(17) . ? C12 H3 0.957(16) . ? C13 N11 1.3283(16) . ? C13 N11 1.3283(16) 2_556 ? C13 H1 0.92(2) . ? C14 C14 1.341(3) 2_556 ? C14 N11 1.3727(19) . ? C14 H2 0.942(19) . ? N1 C1 1.3633(16) 2_556 ? 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 N1 C1 C6 118.97(13) . . ? N1 C1 C2 127.63(13) . . ? C6 C1 C2 113.04(13) . . ? F1 C2 C3 117.02(14) . . ? F1 C2 C1 119.37(13) . . ? C3 C2 C1 123.56(15) . . ? F2 C3 C4 119.38(15) . . ? F2 C3 C2 119.76(17) . . ? C4 C3 C2 120.84(16) . . ? F3 C4 C3 120.88(17) . . ? F3 C4 C5 120.85(17) . . ? C3 C4 C5 118.27(15) . . ? F4 C5 C4 119.94(16) . . ? F4 C5 C6 119.66(17) . . ? C4 C5 C6 120.40(15) . . ? F5 C6 C5 117.97(14) . . ? F5 C6 C1 118.19(13) . . ? C5 C6 C1 123.84(15) . . ? C12 C10 H4 110.4(10) . . ? C12 C10 H5 110.5(11) . . ? H4 C10 H5 109.7(15) . . ? C12 C10 H6 107.0(13) . . ? H4 C10 H6 111.1(16) . . ? H5 C10 H6 108.2(16) . . ? C12 C11 H7 111.8(11) . . ? C12 C11 H8 112.9(12) . . ? H7 C11 H8 104.0(17) . . ? C12 C11 H9 110.2(13) . . ? H7 C11 H9 108.0(17) . . ? H8 C11 H9 109.6(18) . . ? N11 C12 C10 109.83(12) . . ? N11 C12 C11 109.81(14) . . ? C10 C12 C11 113.09(14) . . ? N11 C12 H3 103.9(8) . . ? C10 C12 H3 110.5(9) . . ? C11 C12 H3 109.3(9) . . ? N11 C13 N11 108.68(18) . 2_556 ? N11 C13 H1 125.66(9) . . ? N11 C13 H1 125.66(9) 2_556 . ? C14 C14 N11 107.33(8) 2_556 . ? C14 C14 H2 130.0(11) 2_556 . ? N11 C14 H2 122.7(11) . . ? C1 N1 C1 121.73(17) 2_556 . ? C13 N11 C14 108.33(12) . . ? C13 N11 C12 125.47(13) . . ? C14 N11 C12 126.19(12) . . ? 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 N1 C1 C2 F1 3.2(2) . . . . ? C6 C1 C2 F1 176.22(13) . . . . ? N1 C1 C2 C3 -174.10(14) . . . . ? C6 C1 C2 C3 -1.1(2) . . . . ? F1 C2 C3 F2 2.5(2) . . . . ? C1 C2 C3 F2 179.85(14) . . . . ? F1 C2 C3 C4 -175.86(15) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? F2 C3 C4 F3 1.8(2) . . . . ? C2 C3 C4 F3 -179.87(14) . . . . ? F2 C3 C4 C5 -178.25(14) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? F3 C4 C5 F4 -0.9(2) . . . . ? C3 C4 C5 F4 179.10(15) . . . . ? F3 C4 C5 C6 177.99(14) . . . . ? C3 C4 C5 C6 -2.0(2) . . . . ? F4 C5 C6 F5 1.8(2) . . . . ? C4 C5 C6 F5 -177.08(14) . . . . ? F4 C5 C6 C1 -178.64(13) . . . . ? C4 C5 C6 C1 2.5(2) . . . . ? N1 C1 C6 F5 -7.66(19) . . . . ? C2 C1 C6 F5 178.66(12) . . . . ? N1 C1 C6 C5 172.80(12) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? C6 C1 N1 C1 152.64(14) . . . 2_556 ? C2 C1 N1 C1 -34.70(12) . . . 2_556 ? N11 C13 N11 C14 0.09(8) 2_556 . . . ? N11 C13 N11 C12 -178.74(15) 2_556 . . . ? C14 C14 N11 C13 -0.2(2) 2_556 . . . ? C14 C14 N11 C12 178.57(15) 2_556 . . . ? C10 C12 N11 C13 112.91(15) . . . . ? C11 C12 N11 C13 -122.12(15) . . . . ? C10 C12 N11 C14 -65.71(19) . . . . ? C11 C12 N11 C14 59.25(19) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF