Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Mike Hill' 'Peter B. Hitchcock' 'Ruti Pongtavornpinyo' _publ_contact_author_name 'Dr Mike Hill' _publ_contact_author_address ; Department of Chemistry Imperial College London Exhibition Rd S. Kensington London SW7 2AZ UNITED KINGDOM ; _publ_contact_author_email MIKE.HILL@IMPERIAL.AC.UK _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Neutral Carbene Analogues of the Heaviest Group 13 Elements: Consideration of Electronic and Steric Effects on Structure and Stability ; _publ_requested_category FM data_(4)-may704 _database_code_depnum_ccdc_archive 'CCDC 250588' _audit_creation_date 2004-05-11T10:11:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '(C29 H35 F6 In1 N2), 0.5(C6 H14)' _chemical_formula_sum 'C32 H42 F6 In N2' _chemical_formula_weight 683.5 _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 11.7118(2) _cell_length_b 12.2606(3) _cell_length_c 12.6611(3) _cell_angle_alpha 101.986(1) _cell_angle_beta 94.742(2) _cell_angle_gamma 112.549(1) _cell_volume 1615.74(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16810 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 702 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.789 _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 0.8683 _exptl_absorpt_correction_T_max 0.9615 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.904391E-1 _diffrn_orient_matrix_ub_12 0.268295E-1 _diffrn_orient_matrix_ub_13 0.318817E-1 _diffrn_orient_matrix_ub_21 -0.56115E-2 _diffrn_orient_matrix_ub_22 0.646167E-1 _diffrn_orient_matrix_ub_23 0.595189E-1 _diffrn_orient_matrix_ub_31 -0.24934E-1 _diffrn_orient_matrix_ub_32 -0.589063E-1 _diffrn_orient_matrix_ub_33 0.466668E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 24961 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 5665 _reflns_number_gt 5099 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # 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^)+(0.0344P)^2^+1.7161P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 5665 _refine_ls_number_parameters 399 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.037 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 2.136 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.567 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.31 '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' 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 In In 0.06640(3) 0.66526(4) 0.12346(3) 0.03096(17) Uani 1 1 d . . . F1 F 0.1745(3) 0.9907(3) 0.5001(3) 0.0407(8) Uani 1 1 d . . . F2 F 0.0822(3) 1.0891(3) 0.4348(3) 0.0445(9) Uani 1 1 d . . . F3 F 0.2553(3) 1.0947(3) 0.3876(3) 0.0408(8) Uani 1 1 d . . . F4 F -0.2596(6) 0.9101(7) 0.2160(7) 0.069(3) Uani 0.783(16) 1 d PD . . F5 F -0.2785(9) 0.8239(11) 0.0554(5) 0.092(4) Uani 0.783(16) 1 d PD . . F6 F -0.3493(5) 0.7171(6) 0.1620(11) 0.100(5) Uani 0.783(16) 1 d PD . . N1 N 0.1335(4) 0.8391(4) 0.2735(3) 0.0204(9) Uani 1 1 d . . . N2 N -0.1090(4) 0.7161(4) 0.1152(3) 0.0207(9) Uani 1 1 d . . . C1 C 0.0764(5) 0.9087(4) 0.3110(4) 0.0219(10) Uani 1 1 d . . . C2 C -0.0450(5) 0.8929(5) 0.2699(4) 0.0251(11) Uani 1 1 d . . . H2 H -0.0736 0.95 0.3081 0.03 Uiso 1 1 calc R . . C3 C -0.1296(5) 0.8031(5) 0.1793(4) 0.0226(11) Uani 1 1 d D . . C4 C 0.1467(5) 1.0200(5) 0.4080(5) 0.0295(12) Uani 1 1 d D . . C5 C -0.2559(5) 0.8123(5) 0.1587(5) 0.0345(14) Uani 1 1 d . . . C6 C 0.2563(4) 0.8561(4) 0.3251(4) 0.0207(10) Uani 1 1 d . . . C7 C 0.2638(5) 0.7954(5) 0.4062(4) 0.0272(12) Uani 1 1 d . . . C8 C 0.3805(6) 0.7986(5) 0.4445(5) 0.0364(14) Uani 1 1 d . . . H8 H 0.3875 0.7587 0.5 0.044 Uiso 1 1 calc R . . C9 C 0.4858(6) 0.8585(6) 0.4036(5) 0.0392(15) Uani 1 1 d . . . H9 H 0.5644 0.859 0.43 0.047 Uiso 1 1 calc R . . C10 C 0.4766(5) 0.9173(5) 0.3245(5) 0.0344(13) Uani 1 1 d . . . H10 H 0.5499 0.9591 0.2974 0.041 Uiso 1 1 calc R . . C11 C 0.3630(5) 0.9178(5) 0.2827(4) 0.0250(11) Uani 1 1 d . . . C12 C 0.1477(6) 0.7230(5) 0.4492(5) 0.0355(13) Uani 1 1 d . . . H12 H 0.0792 0.7474 0.426 0.043 Uiso 1 1 calc R . . C13 C 0.1699(8) 0.7503(7) 0.5748(6) 0.059(2) Uani 1 1 d . . . H13A H 0.0928 0.7021 0.5982 0.088 Uiso 1 1 calc R . . H13B H 0.193 0.8376 0.6065 0.088 Uiso 1 1 calc R . . H13C H 0.2379 0.7288 0.5999 0.088 Uiso 1 1 calc R . . C14 C 0.1029(7) 0.5858(6) 0.3976(6) 0.0517(18) Uani 1 1 d . . . H14A H 0.0281 0.5407 0.4257 0.078 Uiso 1 1 calc R . . H14B H 0.1697 0.5599 0.4165 0.078 Uiso 1 1 calc R . . H14C H 0.0821 0.5689 0.3177 0.078 Uiso 1 1 calc R . . C15 C 0.3573(5) 0.9832(5) 0.1942(5) 0.0336(13) Uani 1 1 d . . . H15 H 0.2726 0.9852 0.1844 0.04 Uiso 1 1 calc R . . C16 C 0.4566(7) 1.1158(6) 0.2254(7) 0.0545(19) Uani 1 1 d . . . H16A H 0.4491 1.1542 0.1662 0.082 Uiso 1 1 calc R . . H16B H 0.5407 1.1163 0.2368 0.082 Uiso 1 1 calc R . . H16C H 0.4435 1.1613 0.2932 0.082 Uiso 1 1 calc R . . C17 C 0.3719(8) 0.9137(7) 0.0844(6) 0.0544(18) Uani 1 1 d . . . H17A H 0.3677 0.9574 0.0286 0.082 Uiso 1 1 calc R . . H17B H 0.3042 0.8312 0.0618 0.082 Uiso 1 1 calc R . . H17C H 0.4533 0.908 0.0925 0.082 Uiso 1 1 calc R . . C18 C -0.1931(5) 0.6286(5) 0.0182(4) 0.0219(11) Uani 1 1 d . . . C19 C -0.2771(5) 0.5131(5) 0.0255(4) 0.0242(11) Uani 1 1 d . . . C20 C -0.3422(5) 0.4235(5) -0.0724(5) 0.0323(13) Uani 1 1 d . . . H20 H -0.3995 0.345 -0.0694 0.039 Uiso 1 1 calc R . . C21 C -0.3247(6) 0.4469(6) -0.1728(5) 0.0381(15) Uani 1 1 d . . . H21 H -0.369 0.3845 -0.2383 0.046 Uiso 1 1 calc R . . C22 C -0.2431(6) 0.5609(6) -0.1786(5) 0.0366(14) Uani 1 1 d . . . H22 H -0.2329 0.5764 -0.2484 0.044 Uiso 1 1 calc R . . C23 C -0.1750(5) 0.6540(5) -0.0841(4) 0.0276(12) Uani 1 1 d . . . C24 C -0.2973(5) 0.4833(5) 0.1348(5) 0.0295(12) Uani 1 1 d . . . H24 H -0.2588 0.5621 0.1935 0.035 Uiso 1 1 calc R . . C25 C -0.2320(6) 0.4022(6) 0.1592(5) 0.0420(15) Uani 1 1 d . . . H25A H -0.2465 0.385 0.2303 0.063 Uiso 1 1 calc R . . H25B H -0.1415 0.4445 0.1613 0.063 Uiso 1 1 calc R . . H25C H -0.266 0.3252 0.1015 0.063 Uiso 1 1 calc R . . C26 C -0.4366(6) 0.4230(7) 0.1413(6) 0.0500(17) Uani 1 1 d . . . H26A H -0.4451 0.4059 0.2132 0.075 Uiso 1 1 calc R . . H26B H -0.4774 0.3462 0.0835 0.075 Uiso 1 1 calc R . . H26C H -0.4766 0.478 0.1313 0.075 Uiso 1 1 calc R . . C27 C -0.0851(6) 0.7780(6) -0.0938(5) 0.0386(14) Uani 1 1 d . . . H27 H -0.0474 0.8319 -0.0178 0.046 Uiso 1 1 calc R . . C28 C -0.1534(9) 0.8381(10) -0.1526(11) 0.100(4) Uani 1 1 d . . . H28A H -0.093 0.918 -0.1569 0.15 Uiso 1 1 calc R . . H28B H -0.2176 0.8489 -0.1118 0.15 Uiso 1 1 calc R . . H28C H -0.1936 0.7861 -0.2269 0.15 Uiso 1 1 calc R . . C29 C 0.0211(8) 0.7703(8) -0.1501(9) 0.077(3) Uani 1 1 d . . . H29A H 0.0768 0.8521 -0.1544 0.116 Uiso 1 1 calc R . . H29B H -0.0132 0.7161 -0.2244 0.116 Uiso 1 1 calc R . . H29C H 0.0687 0.7378 -0.1083 0.116 Uiso 1 1 calc R . . F4A F -0.268(2) 0.913(2) 0.163(3) 0.13(2) Uani 0.217(16) 1 d PD . . F5A F -0.3299(12) 0.7427(16) 0.0825(15) 0.030(6) Uani 0.217(16) 1 d PD . . F6A F -0.3247(15) 0.777(2) 0.2458(14) 0.047(7) Uani 0.217(16) 1 d PD . . C1S C 0.4338(9) 1.4943(8) 0.5047(7) 0.081(3) Uani 1 1 d . . . H1S1 H 0.4392 1.5721 0.5517 0.097 Uiso 1 1 calc R . . H1S2 H 0.3884 1.4825 0.4309 0.097 Uiso 1 1 calc R . . C2S C 0.3581(11) 1.3916(7) 0.5514(8) 0.085(3) Uani 1 1 d . . . H2S1 H 0.4011 1.4052 0.6267 0.102 Uiso 1 1 calc R . . H2S2 H 0.3554 1.3139 0.5064 0.102 Uiso 1 1 calc R . . C3S C 0.2242(10) 1.3787(8) 0.5554(8) 0.084(3) Uani 1 1 d . . . H3S1 H 0.1802 1.3101 0.586 0.126 Uiso 1 1 calc R . . H3S2 H 0.1803 1.3636 0.481 0.126 Uiso 1 1 calc R . . H3S3 H 0.2259 1.4543 0.6017 0.126 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 In 0.0234(2) 0.0349(3) 0.0312(3) -0.00475(17) -0.00255(16) 0.01667(18) F1 0.043(2) 0.043(2) 0.0264(17) -0.0045(15) -0.0020(14) 0.0154(16) F2 0.0351(19) 0.0339(19) 0.053(2) -0.0153(16) -0.0042(16) 0.0184(15) F3 0.0281(18) 0.0262(17) 0.049(2) -0.0048(15) 0.0045(15) -0.0009(14) F4 0.030(3) 0.059(5) 0.097(6) -0.040(4) -0.030(3) 0.037(3) F5 0.104(7) 0.169(11) 0.056(4) 0.025(5) 0.002(4) 0.116(8) F6 0.022(3) 0.052(4) 0.241(17) 0.058(7) 0.043(5) 0.017(3) N1 0.015(2) 0.021(2) 0.022(2) 0.0042(17) 0.0018(16) 0.0055(17) N2 0.016(2) 0.022(2) 0.023(2) 0.0048(18) 0.0010(16) 0.0075(17) C1 0.021(3) 0.021(3) 0.022(3) 0.005(2) 0.004(2) 0.006(2) C2 0.020(3) 0.023(3) 0.030(3) 0.000(2) 0.004(2) 0.011(2) C3 0.017(2) 0.023(3) 0.029(3) 0.007(2) 0.005(2) 0.010(2) C4 0.022(3) 0.028(3) 0.033(3) -0.001(2) 0.002(2) 0.009(2) C5 0.021(3) 0.027(3) 0.050(4) -0.002(3) -0.003(3) 0.012(3) C6 0.017(2) 0.019(2) 0.022(3) -0.001(2) -0.0012(19) 0.007(2) C7 0.033(3) 0.022(3) 0.022(3) 0.002(2) -0.001(2) 0.010(2) C8 0.043(4) 0.033(3) 0.030(3) 0.002(3) -0.010(3) 0.020(3) C9 0.026(3) 0.037(3) 0.047(4) -0.004(3) -0.012(3) 0.015(3) C10 0.018(3) 0.031(3) 0.047(4) 0.001(3) 0.003(2) 0.007(2) C11 0.020(3) 0.020(3) 0.031(3) 0.002(2) 0.004(2) 0.006(2) C12 0.042(3) 0.034(3) 0.030(3) 0.014(3) 0.010(3) 0.012(3) C13 0.078(5) 0.063(5) 0.033(4) 0.019(3) 0.017(4) 0.022(4) C14 0.063(5) 0.036(4) 0.046(4) 0.016(3) 0.015(3) 0.006(3) C15 0.027(3) 0.031(3) 0.042(3) 0.015(3) 0.011(2) 0.008(2) C16 0.045(4) 0.036(4) 0.080(5) 0.028(4) 0.018(4) 0.007(3) C17 0.065(5) 0.055(4) 0.046(4) 0.021(3) 0.027(4) 0.021(4) C18 0.018(2) 0.024(3) 0.023(3) 0.001(2) -0.002(2) 0.012(2) C19 0.018(3) 0.023(3) 0.030(3) 0.002(2) 0.001(2) 0.011(2) C20 0.023(3) 0.026(3) 0.041(3) -0.003(2) -0.003(2) 0.011(2) C21 0.036(3) 0.041(4) 0.029(3) -0.011(3) -0.011(2) 0.020(3) C22 0.041(3) 0.051(4) 0.022(3) 0.005(3) 0.000(2) 0.027(3) C23 0.026(3) 0.034(3) 0.028(3) 0.009(2) 0.002(2) 0.018(2) C24 0.029(3) 0.022(3) 0.034(3) 0.005(2) 0.006(2) 0.009(2) C25 0.048(4) 0.047(4) 0.039(4) 0.015(3) 0.006(3) 0.026(3) C26 0.035(4) 0.049(4) 0.073(5) 0.030(4) 0.023(3) 0.016(3) C27 0.046(4) 0.042(4) 0.035(3) 0.017(3) 0.010(3) 0.020(3) C28 0.076(6) 0.092(7) 0.175(11) 0.100(8) 0.031(7) 0.045(6) C29 0.060(5) 0.072(6) 0.112(8) 0.036(5) 0.049(5) 0.026(5) F4A 0.10(2) 0.031(15) 0.22(6) 0.03(2) -0.07(3) 0.019(14) F5A 0.005(7) 0.018(11) 0.051(12) -0.008(8) -0.003(7) -0.001(7) F6A 0.042(11) 0.084(18) 0.037(11) 0.019(10) 0.035(9) 0.041(12) C1S 0.119(8) 0.047(5) 0.064(5) 0.000(4) -0.029(6) 0.037(5) C2S 0.131(9) 0.041(5) 0.071(6) 0.000(4) -0.022(6) 0.038(5) C3S 0.116(9) 0.051(5) 0.070(6) -0.002(4) -0.014(6) 0.034(5) #----------------------------------------------------------------------------# # 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 In N1 2.357(4) . ? In N2 2.364(4) . ? F1 C4 1.340(7) . ? F2 C4 1.347(6) . ? F3 C4 1.336(6) . ? F4 C5 1.284(8) . ? F5 C5 1.360(9) . ? F6 C5 1.269(8) . ? N1 C1 1.312(6) . ? N1 C6 1.448(6) . ? N2 C3 1.313(6) . ? N2 C18 1.439(6) . ? C1 C2 1.398(7) . ? C1 C4 1.524(7) . ? C2 C3 1.400(7) . ? C3 C5 1.532(7) . ? C5 F5A 1.167(14) . ? C5 F4A 1.29(2) . ? C5 F6A 1.461(16) . ? C6 C7 1.404(7) . ? C6 C11 1.406(7) . ? C7 C8 1.394(8) . ? C7 C12 1.526(8) . ? C8 C9 1.378(9) . ? C9 C10 1.369(9) . ? C10 C11 1.393(8) . ? C11 C15 1.518(8) . ? C12 C14 1.530(9) . ? C12 C13 1.534(9) . ? C15 C17 1.533(9) . ? C15 C16 1.536(8) . ? C18 C23 1.407(7) . ? C18 C19 1.409(7) . ? C19 C20 1.400(8) . ? C19 C24 1.517(8) . ? C20 C21 1.375(9) . ? C21 C22 1.379(9) . ? C22 C23 1.395(8) . ? C23 C27 1.520(8) . ? C24 C26 1.528(8) . ? C24 C25 1.530(8) . ? C27 C29 1.507(10) . ? C27 C28 1.522(10) . ? C1S C2S 1.503(14) . ? C1S C1S 1.52(2) 2_686 ? C2S C3S 1.521(14) . ? 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 In N2 78.23(14) . . ? C1 N1 C6 123.4(4) . . ? C1 N1 In 130.6(3) . . ? C6 N1 In 105.9(3) . . ? C3 N2 C18 125.8(4) . . ? C3 N2 In 130.7(3) . . ? C18 N2 In 103.5(3) . . ? N1 C1 C2 126.5(5) . . ? N1 C1 C4 118.7(4) . . ? C2 C1 C4 114.8(4) . . ? C1 C2 C3 127.9(5) . . ? N2 C3 C2 126.0(5) . . ? N2 C3 C5 120.2(5) . . ? C2 C3 C5 113.8(4) . . ? F3 C4 F1 106.6(4) . . ? F3 C4 F2 105.9(4) . . ? F1 C4 F2 105.4(4) . . ? F3 C4 C1 111.7(4) . . ? F1 C4 C1 113.1(4) . . ? F2 C4 C1 113.5(4) . . ? F6 C5 F4 111.8(7) . . ? F5A C5 F4A 104.4(13) . . ? F6 C5 F5 104.3(8) . . ? F4 C5 F5 100.8(6) . . ? F5A C5 F6A 99.4(12) . . ? F4A C5 F6A 98.3(17) . . ? F5A C5 C3 117.7(8) . . ? F6 C5 C3 113.6(5) . . ? F4 C5 C3 114.9(5) . . ? F4A C5 C3 124.2(12) . . ? F5 C5 C3 110.1(5) . . ? F6A C5 C3 108.4(8) . . ? C7 C6 C11 121.1(5) . . ? C7 C6 N1 118.7(4) . . ? C11 C6 N1 119.5(4) . . ? C8 C7 C6 118.2(5) . . ? C8 C7 C12 120.1(5) . . ? C6 C7 C12 121.7(5) . . ? C9 C8 C7 121.3(5) . . ? C10 C9 C8 119.6(5) . . ? C9 C10 C11 122.0(5) . . ? C10 C11 C6 117.7(5) . . ? C10 C11 C15 120.1(5) . . ? C6 C11 C15 122.2(5) . . ? C7 C12 C14 110.5(5) . . ? C7 C12 C13 112.6(5) . . ? C14 C12 C13 110.4(5) . . ? C11 C15 C17 110.9(5) . . ? C11 C15 C16 112.4(5) . . ? C17 C15 C16 109.7(5) . . ? C23 C18 C19 121.3(5) . . ? C23 C18 N2 118.3(4) . . ? C19 C18 N2 119.6(4) . . ? C20 C19 C18 117.9(5) . . ? C20 C19 C24 119.8(5) . . ? C18 C19 C24 122.3(5) . . ? C21 C20 C19 121.3(5) . . ? C20 C21 C22 120.0(5) . . ? C21 C22 C23 121.5(5) . . ? C22 C23 C18 117.9(5) . . ? C22 C23 C27 119.9(5) . . ? C18 C23 C27 122.2(5) . . ? C19 C24 C26 112.3(5) . . ? C19 C24 C25 111.6(5) . . ? C26 C24 C25 109.8(5) . . ? C29 C27 C23 112.2(6) . . ? C29 C27 C28 110.1(7) . . ? C23 C27 C28 111.5(6) . . ? C2S C1S C1S 114.8(9) . 2_686 ? C1S C2S C3S 113.7(8) . . ? #===END data_(5)-aug504 _database_code_depnum_ccdc_archive 'CCDC 250589' _audit_creation_date 2004-08-13T14:19:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C29 H41 N2 Tl1' _chemical_formula_sum 'C29 H41 N2 Tl1' _chemical_formula_weight 622.01 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.8500(3) _cell_length_b 17.4867(5) _cell_length_c 12.8901(2) _cell_angle_alpha 90 _cell_angle_beta 102.355(1) _cell_angle_gamma 90 _cell_volume 2829.38(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 24159 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.46 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.725 _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 0.3408 _exptl_absorpt_correction_T_max 0.44 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.324948E-1 _diffrn_orient_matrix_ub_12 -0.199777E-1 _diffrn_orient_matrix_ub_13 0.723735E-1 _diffrn_orient_matrix_ub_21 -0.68957E-1 _diffrn_orient_matrix_ub_22 0.83512E-2 _diffrn_orient_matrix_ub_23 0.224523E-1 _diffrn_orient_matrix_ub_31 -0.231453E-1 _diffrn_orient_matrix_ub_32 -0.529285E-1 _diffrn_orient_matrix_ub_33 -0.237746E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_unetI/netI 0.037 _diffrn_reflns_number 38836 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4975 _reflns_number_gt 4093 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # 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^)+(0.0143P)^2^+17.6625P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 4975 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.694 _refine_diff_density_min -2.468 _refine_diff_density_rms 0.115 #----------------------------------------------------------------------------# # 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' Tl Tl -2.8358 9.6688 '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 Tl Tl -0.00518(2) 0.067681(19) 0.87836(2) 0.05550(12) Uani 1 1 d . . . N1 N -0.1858(3) 0.0448(3) 0.7800(4) 0.0262(10) Uani 1 1 d . . . N2 N -0.0159(3) 0.1418(3) 0.7195(3) 0.0262(10) Uani 1 1 d . . . C1 C -0.2388(4) 0.0717(3) 0.6891(4) 0.0289(12) Uani 1 1 d . . . C2 C -0.1971(4) 0.1232(3) 0.6246(4) 0.0286(13) Uani 1 1 d . . . H2 H -0.2467 0.1401 0.5634 0.034 Uiso 1 1 calc R . . C3 C -0.0943(4) 0.1537(3) 0.6358(4) 0.0257(12) Uani 1 1 d . . . C4 C -0.3537(5) 0.0468(4) 0.6470(5) 0.0437(17) Uani 1 1 d . . . H4A H -0.3552 -0.0074 0.6273 0.066 Uiso 1 1 calc R . . H4B H -0.385 0.0774 0.5844 0.066 Uiso 1 1 calc R . . H4C H -0.3947 0.0543 0.7021 0.066 Uiso 1 1 calc R . . C5 C -0.0744(5) 0.2024(4) 0.5450(5) 0.0378(15) Uani 1 1 d . . . H5A H -0.0473 0.2525 0.5721 0.057 Uiso 1 1 calc R . . H5B H -0.1411 0.2089 0.4924 0.057 Uiso 1 1 calc R . . H5C H -0.0217 0.1772 0.5117 0.057 Uiso 1 1 calc R . . C6 C -0.2333(4) -0.0064(3) 0.8433(4) 0.0258(12) Uani 1 1 d . . . C7 C -0.2875(4) 0.0237(3) 0.9181(5) 0.0300(13) Uani 1 1 d . . . C8 C -0.3183(5) -0.0261(4) 0.9904(5) 0.0383(15) Uani 1 1 d . . . H8 H -0.3544 -0.0066 1.0419 0.046 Uiso 1 1 calc R . . C9 C -0.2974(5) -0.1028(4) 0.9884(5) 0.0407(16) Uani 1 1 d . . . H9 H -0.3172 -0.1358 1.0394 0.049 Uiso 1 1 calc R . . C10 C -0.2475(5) -0.1324(4) 0.9125(5) 0.0353(14) Uani 1 1 d . . . H10 H -0.2352 -0.1859 0.9108 0.042 Uiso 1 1 calc R . . C11 C -0.2150(4) -0.0856(3) 0.8388(4) 0.0286(13) Uani 1 1 d . . . C12 C -0.3122(5) 0.1085(4) 0.9223(5) 0.0390(15) Uani 1 1 d . . . H12 H -0.2925 0.1332 0.8592 0.047 Uiso 1 1 calc R . . C13 C -0.2450(7) 0.1453(4) 1.0211(6) 0.067(2) Uani 1 1 d . . . H13A H -0.2622 0.1999 1.022 0.1 Uiso 1 1 calc R . . H13B H -0.1693 0.1392 1.0205 0.1 Uiso 1 1 calc R . . H13C H -0.2602 0.1206 1.0845 0.1 Uiso 1 1 calc R . . C14 C -0.4310(6) 0.1239(5) 0.9158(8) 0.072(3) Uani 1 1 d . . . H14A H -0.4431 0.1792 0.9181 0.108 Uiso 1 1 calc R . . H14B H -0.4531 0.0993 0.976 0.108 Uiso 1 1 calc R . . H14C H -0.4727 0.103 0.8492 0.108 Uiso 1 1 calc R . . C15 C -0.1605(5) -0.1192(4) 0.7558(5) 0.0360(14) Uani 1 1 d . . . H15 H -0.1508 -0.077 0.7064 0.043 Uiso 1 1 calc R . . C16 C -0.2282(6) -0.1807(5) 0.6898(6) 0.066(2) Uani 1 1 d . . . H16A H -0.1907 -0.2007 0.6369 0.099 Uiso 1 1 calc R . . H16B H -0.2964 -0.1586 0.6536 0.099 Uiso 1 1 calc R . . H16C H -0.2411 -0.2223 0.7364 0.099 Uiso 1 1 calc R . . C17 C -0.0507(6) -0.1508(6) 0.8047(7) 0.083(3) Uani 1 1 d . . . H17A H -0.018 -0.1714 0.7485 0.125 Uiso 1 1 calc R . . H17B H -0.0574 -0.1916 0.855 0.125 Uiso 1 1 calc R . . H17C H -0.0059 -0.1097 0.8421 0.125 Uiso 1 1 calc R . . C18 C 0.0876(4) 0.1739(3) 0.7232(4) 0.0249(12) Uani 1 1 d . . . C19 C 0.1119(4) 0.2461(3) 0.7691(5) 0.0314(13) Uani 1 1 d . . . C20 C 0.2171(5) 0.2724(4) 0.7840(5) 0.0424(16) Uani 1 1 d . . . H20 H 0.2353 0.3211 0.8154 0.051 Uiso 1 1 calc R . . C21 C 0.2942(5) 0.2284(4) 0.7537(6) 0.0481(18) Uani 1 1 d . . . H21 H 0.3655 0.2465 0.7655 0.058 Uiso 1 1 calc R . . C22 C 0.2690(5) 0.1584(4) 0.7065(5) 0.0448(17) Uani 1 1 d . . . H22 H 0.3229 0.129 0.685 0.054 Uiso 1 1 calc R . . C23 C 0.1648(5) 0.1299(3) 0.6896(5) 0.0336(14) Uani 1 1 d . . . C24 C 0.0276(5) 0.2950(4) 0.8036(5) 0.0442(16) Uani 1 1 d . . . H24 H -0.0431 0.2742 0.7663 0.053 Uiso 1 1 calc R . . C25 C 0.0328(7) 0.2864(6) 0.9232(6) 0.083(3) Uani 1 1 d . . . H25A H -0.0225 0.3181 0.9435 0.124 Uiso 1 1 calc R . . H25B H 0.103 0.3029 0.963 0.124 Uiso 1 1 calc R . . H25C H 0.0213 0.2327 0.9396 0.124 Uiso 1 1 calc R . . C26 C 0.0309(7) 0.3780(4) 0.7698(10) 0.102(4) Uani 1 1 d . . . H26A H -0.0252 0.4067 0.7936 0.154 Uiso 1 1 calc R . . H26B H 0.0195 0.3808 0.6923 0.154 Uiso 1 1 calc R . . H26C H 0.1005 0.3999 0.8019 0.154 Uiso 1 1 calc R . . C27 C 0.1373(6) 0.0534(4) 0.6357(5) 0.0484(18) Uani 1 1 d . . . H27 H 0.0586 0.0465 0.6268 0.058 Uiso 1 1 calc R . . C28 C 0.1898(8) -0.0122(5) 0.7040(9) 0.093(3) Uani 1 1 d . . . H28A H 0.1697 -0.0606 0.6669 0.14 Uiso 1 1 calc R . . H28B H 0.1664 -0.0122 0.7715 0.14 Uiso 1 1 calc R . . H28C H 0.2674 -0.0061 0.7177 0.14 Uiso 1 1 calc R . . C29 C 0.1608(10) 0.0521(6) 0.5249(8) 0.110(4) Uani 1 1 d . . . H29A H 0.1415 0.002 0.4923 0.165 Uiso 1 1 calc R . . H29B H 0.2369 0.0614 0.5298 0.165 Uiso 1 1 calc R . . H29C H 0.1191 0.092 0.4813 0.165 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 Tl 0.03764(15) 0.0887(2) 0.03408(15) 0.02638(15) -0.00588(10) -0.02673(15) N1 0.020(2) 0.029(3) 0.030(3) 0.001(2) 0.007(2) -0.0030(19) N2 0.023(2) 0.030(3) 0.026(2) -0.001(2) 0.005(2) -0.002(2) C1 0.027(3) 0.029(3) 0.030(3) -0.003(3) 0.003(2) 0.002(3) C2 0.028(3) 0.030(3) 0.024(3) 0.005(2) -0.003(2) 0.000(2) C3 0.028(3) 0.023(3) 0.027(3) -0.001(2) 0.006(2) 0.002(2) C4 0.027(3) 0.053(5) 0.047(4) 0.011(3) -0.001(3) -0.010(3) C5 0.039(3) 0.038(4) 0.034(3) 0.014(3) 0.002(3) -0.003(3) C6 0.020(3) 0.030(3) 0.026(3) -0.001(2) 0.002(2) -0.004(2) C7 0.024(3) 0.030(3) 0.038(3) -0.005(3) 0.010(3) -0.005(2) C8 0.040(4) 0.040(4) 0.040(4) -0.005(3) 0.018(3) -0.011(3) C9 0.046(4) 0.039(4) 0.041(4) 0.002(3) 0.018(3) -0.015(3) C10 0.040(3) 0.030(4) 0.037(3) 0.000(3) 0.010(3) -0.004(3) C11 0.023(3) 0.033(4) 0.029(3) -0.002(3) 0.003(2) -0.002(2) C12 0.041(4) 0.039(4) 0.040(4) -0.003(3) 0.016(3) -0.004(3) C13 0.100(7) 0.030(4) 0.062(5) -0.006(4) 0.000(5) -0.002(4) C14 0.055(5) 0.060(6) 0.111(7) 0.000(5) 0.039(5) 0.017(4) C15 0.035(3) 0.033(4) 0.040(4) -0.005(3) 0.009(3) 0.002(3) C16 0.073(5) 0.067(6) 0.063(5) -0.033(4) 0.023(4) -0.017(4) C17 0.054(5) 0.128(9) 0.068(6) -0.011(6) 0.013(4) 0.042(5) C18 0.025(3) 0.026(3) 0.025(3) 0.009(2) 0.007(2) 0.000(2) C19 0.030(3) 0.027(3) 0.034(3) 0.004(3) 0.002(3) -0.003(3) C20 0.032(3) 0.036(4) 0.054(4) 0.013(3) -0.003(3) -0.009(3) C21 0.024(3) 0.058(5) 0.062(5) 0.022(4) 0.007(3) -0.001(3) C22 0.034(4) 0.056(5) 0.048(4) 0.017(4) 0.019(3) 0.011(3) C23 0.036(3) 0.037(4) 0.030(3) 0.009(3) 0.010(3) 0.005(3) C24 0.036(4) 0.035(4) 0.058(4) -0.015(3) 0.003(3) 0.004(3) C25 0.056(5) 0.127(9) 0.062(5) -0.041(6) 0.005(4) 0.016(5) C26 0.066(6) 0.032(5) 0.211(13) -0.001(6) 0.035(7) 0.014(4) C27 0.051(4) 0.043(5) 0.053(4) -0.006(3) 0.014(3) 0.012(3) C28 0.112(8) 0.037(5) 0.120(9) -0.004(5) -0.002(7) 0.021(5) C29 0.167(11) 0.107(9) 0.072(7) -0.036(6) 0.060(7) 0.002(8) #----------------------------------------------------------------------------# # 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 Tl N2 2.403(4) . ? Tl N1 2.428(4) . ? N1 C1 1.310(7) . ? N1 C6 1.433(7) . ? N2 C3 1.325(7) . ? N2 C18 1.435(7) . ? C1 C2 1.408(8) . ? C1 C4 1.523(8) . ? C2 C3 1.402(7) . ? C3 C5 1.513(8) . ? C6 C7 1.407(8) . ? C6 C11 1.408(8) . ? C7 C8 1.393(8) . ? C7 C12 1.520(8) . ? C8 C9 1.370(9) . ? C9 C10 1.380(9) . ? C10 C11 1.385(8) . ? C11 C15 1.518(8) . ? C12 C13 1.521(9) . ? C12 C14 1.535(9) . ? C15 C17 1.521(9) . ? C15 C16 1.523(9) . ? C18 C23 1.395(8) . ? C18 C19 1.401(8) . ? C19 C20 1.401(8) . ? C19 C24 1.519(8) . ? C20 C21 1.376(9) . ? C21 C22 1.374(10) . ? C22 C23 1.401(9) . ? C23 C27 1.515(9) . ? C24 C26 1.518(10) . ? C24 C25 1.537(10) . ? C27 C28 1.514(10) . ? C27 C29 1.522(11) . ? 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 N2 Tl N1 76.67(15) . . ? C1 N1 C6 122.0(4) . . ? C1 N1 Tl 131.7(4) . . ? C6 N1 Tl 106.4(3) . . ? C3 N2 C18 120.3(4) . . ? C3 N2 Tl 132.3(4) . . ? C18 N2 Tl 107.4(3) . . ? N1 C1 C2 124.5(5) . . ? N1 C1 C4 119.7(5) . . ? C2 C1 C4 115.8(5) . . ? C3 C2 C1 130.7(5) . . ? N2 C3 C2 124.0(5) . . ? N2 C3 C5 119.5(5) . . ? C2 C3 C5 116.5(5) . . ? C7 C6 C11 120.5(5) . . ? C7 C6 N1 119.4(5) . . ? C11 C6 N1 119.8(5) . . ? C8 C7 C6 118.6(5) . . ? C8 C7 C12 119.7(5) . . ? C6 C7 C12 121.7(5) . . ? C9 C8 C7 120.9(6) . . ? C8 C9 C10 120.3(6) . . ? C9 C10 C11 121.2(6) . . ? C10 C11 C6 118.4(5) . . ? C10 C11 C15 120.5(5) . . ? C6 C11 C15 121.1(5) . . ? C7 C12 C13 110.9(6) . . ? C7 C12 C14 112.4(5) . . ? C13 C12 C14 110.6(6) . . ? C11 C15 C17 112.0(5) . . ? C11 C15 C16 111.9(5) . . ? C17 C15 C16 110.1(6) . . ? C23 C18 C19 121.3(5) . . ? C23 C18 N2 119.3(5) . . ? C19 C18 N2 119.2(5) . . ? C18 C19 C20 118.3(6) . . ? C18 C19 C24 121.5(5) . . ? C20 C19 C24 120.2(6) . . ? C21 C20 C19 120.7(6) . . ? C22 C21 C20 120.5(6) . . ? C21 C22 C23 120.8(6) . . ? C18 C23 C22 118.4(6) . . ? C18 C23 C27 121.2(5) . . ? C22 C23 C27 120.5(6) . . ? C26 C24 C19 112.8(6) . . ? C26 C24 C25 112.5(7) . . ? C19 C24 C25 111.0(6) . . ? C28 C27 C23 111.8(6) . . ? C28 C27 C29 112.4(7) . . ? C23 C27 C29 111.7(7) . . ? #===END