# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/493 data_k56 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ' "NORBORNADIEN EXO" ' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C35 H39 Cl18 N9 Sb2' _chemical_formula_weight 1467.35 _chemical_melting_point 205_C _chemical_compound_source ? 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' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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 9.537(3) _cell_length_b 10.640(4) _cell_length_c 27.931(11) _cell_angle_alpha 90.85(2) _cell_angle_beta 92.16(2) _cell_angle_gamma 89.99(2) _cell_volume 2831.9(18) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.010 _cell_measurement_theta_max 19.051 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.08 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method ? _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.840 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 0.9991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius-CAD4 4-circle-diffractometer' _diffrn_measurement_method '\w/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 42.3 _diffrn_reflns_number 8824 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.00 _reflns_number_total 8215 _reflns_number_observed 7179 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD4' _computing_cell_refinement 'Enraf Nonius CAD4' _computing_data_reduction 'Enraf Nonius MolEN (1990)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP,SCHAKAL 93' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 167 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1099P)^2^+18.3521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom (H812,H813,H922,H923,H12,H13,H14)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8048 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_obs 0.0570 _refine_ls_wR_factor_all 0.3901 _refine_ls_wR_factor_obs 0.1558 _refine_ls_goodness_of_fit_all 1.070 _refine_ls_goodness_of_fit_obs 0.990 _refine_ls_restrained_S_all 2.440 _refine_ls_restrained_S_obs 0.990 _refine_ls_shift/esd_max -0.049 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sb1 Sb 0.28376(5) 0.28377(4) 0.11706(2) 0.0311(2) Uani 1 d . . Cl11 Cl 0.5157(2) 0.3311(2) 0.09517(8) 0.0491(5) Uani 1 d . . Cl12 Cl 0.0494(2) 0.2421(2) 0.13637(10) 0.0601(6) Uani 1 d . . Cl13 Cl 0.3293(3) 0.0684(2) 0.10741(13) 0.0787(9) Uani 1 d . . Cl14 Cl 0.2426(4) 0.5008(2) 0.1255(2) 0.1040(14) Uani 1 d . . Cl15 Cl 0.2129(3) 0.2942(3) 0.03536(10) 0.0767(8) Uani 1 d . . Cl16 Cl 0.3529(3) 0.2712(4) 0.19752(10) 0.0951(12) Uani 1 d . . Sb2 Sb 0.35973(5) 0.97271(4) 0.62963(2) 0.0303(2) Uani 1 d . . Cl21 Cl 0.4274(3) 1.1726(2) 0.66047(11) 0.0615(7) Uani 1 d . . Cl22 Cl 0.2877(3) 0.7763(2) 0.59767(10) 0.0619(7) Uani 1 d . . Cl23 Cl 0.5836(2) 0.9471(2) 0.59733(10) 0.0595(6) Uani 1 d . . Cl24 Cl 0.2794(3) 1.0677(3) 0.55807(10) 0.0667(7) Uani 1 d . . Cl25 Cl 0.1353(3) 0.9979(3) 0.66106(10) 0.0663(7) Uani 1 d . . Cl26 Cl 0.4440(3) 0.8797(3) 0.70090(10) 0.0734(8) Uani 1 d . . Cl31 Cl 0.1764(2) 0.3911(2) 0.62183(7) 0.0439(5) Uani 1 d . . Cl32 Cl -0.1297(3) 0.7258(2) 0.52178(9) 0.0639(7) Uani 1 d . . Cl33 Cl -0.0946(3) 0.7646(2) 0.71282(8) 0.0548(6) Uani 1 d . . Cl41 Cl -0.1285(2) 0.2000(2) 0.91903(8) 0.0478(5) Uani 1 d . . Cl42 Cl 0.3262(3) -0.0571(2) 0.97905(9) 0.0659(7) Uani 1 d . . Cl43 Cl 0.2142(2) -0.0104(2) 0.79122(7) 0.0429(5) Uani 1 d . . N1 N 0.0857(6) 0.5405(5) 0.7081(2) 0.0266(13) Uani 1 d . . N2 N 0.2106(7) 0.5615(5) 0.7194(2) 0.0312(14) Uani 1 d . . N3 N -0.0335(6) 0.1460(5) 0.8216(2) 0.0251(13) Uani 1 d . . N4 N -0.1167(6) 0.0820(5) 0.7961(2) 0.0298(13) Uani 1 d . . C1 C -0.0249(7) 0.2835(6) 0.8115(3) 0.0265(15) Uani 1 d . . C2 C -0.1327(7) 0.2984(6) 0.7695(3) 0.0254(15) Uani 1 d . . C3 C -0.0397(7) 0.3408(6) 0.7292(3) 0.027(2) Uani 1 d . . C4 C 0.0006(7) 0.4772(6) 0.7447(2) 0.0251(15) Uani 1 d . . C5 C 0.1058(8) 0.4621(6) 0.7868(3) 0.029(2) Uani 1 d . . C6 C 0.1169(7) 0.3183(6) 0.7913(2) 0.0224(14) Uani 1 d . . C7 C 0.0992(7) 0.2732(6) 0.7394(2) 0.0238(14) Uani 1 d . . C8 C -0.1998(8) 0.1642(6) 0.7637(3) 0.030(2) Uani 1 d . . C81 C -0.3457(9) 0.1623(7) 0.7856(3) 0.040(2) Uani 1 d . . C82 C -0.2057(9) 0.1065(7) 0.7139(3) 0.037(2) Uani 1 d . . C9 C 0.2399(8) 0.5306(6) 0.7703(3) 0.030(2) Uani 1 d . . C91 C 0.2526(9) 0.6616(7) 0.7936(3) 0.042(2) Uani 1 d . . C92 C 0.3783(8) 0.4596(8) 0.7752(3) 0.041(2) Uani 1 d . . C10 C 0.0303(7) 0.5799(6) 0.6621(3) 0.027(2) Uani 1 d . . C11 C 0.0659(8) 0.5199(6) 0.6198(3) 0.030(2) Uani 1 d . . C12 C 0.0147(8) 0.5630(7) 0.5768(3) 0.035(2) Uani 1 d . . C13 C -0.0702(9) 0.6673(7) 0.5760(3) 0.039(2) Uani 1 d . . C14 C -0.1070(8) 0.7299(7) 0.6177(3) 0.040(2) Uani 1 d . . C15 C -0.0558(8) 0.6860(7) 0.6603(3) 0.036(2) Uani 1 d . . C16 C 0.0522(8) 0.0901(6) 0.8594(2) 0.027(2) Uani 1 d . . C17 C 0.0182(8) 0.1131(6) 0.9068(3) 0.033(2) Uani 1 d . . C18 C 0.1016(10) 0.0658(7) 0.9439(3) 0.041(2) Uani 1 d . . C19 C 0.2182(9) -0.0030(7) 0.9323(3) 0.039(2) Uani 1 d . . C20 C 0.2528(8) -0.0299(6) 0.8861(3) 0.035(2) Uani 1 d . . C21 C 0.1691(8) 0.0179(6) 0.8493(3) 0.030(2) Uani 1 d . . N11L N 0.1715(12) 0.7156(11) 0.3923(4) 0.085(3) Uani 1 d . . C12L C 0.1472(11) 0.7972(11) 0.4175(4) 0.062(3) Uani 1 d . . C11L C 0.1179(13) 0.8976(12) 0.4507(5) 0.079(3) Uani 1 d . . N22L N 0.1402(11) 0.4229(9) 0.9070(3) 0.072(2) Uani 1 d . . C22L C 0.1463(9) 0.5028(10) 0.9343(3) 0.050(2) Uani 1 d . . C21L C 0.1582(12) 0.6045(11) 0.9694(4) 0.068(3) Uani 1 d . . N33L C 0.2959(14) 0.5519(10) 0.5040(4) 0.076(4) Uani 1 d . . C32L C 0.3733(14) 0.6248(11) 0.4960(4) 0.069(3) Uani 1 d . . C31L C 0.4780(12) 0.7212(11) 0.4843(5) 0.075(3) Uani 1 d . . N44L N 0.3294(10) 0.5140(11) 0.2973(4) 0.080(3) Uani 1 d . . C42L C 0.3767(10) 0.4955(9) 0.3343(4) 0.052(2) Uani 1 d . . C41L C 0.4356(14) 0.4667(15) 0.3802(5) 0.089(4) Uani 1 d . . N55L N 0.4163(11) 0.2314(10) 0.8673(4) 0.078(3) Uani 1 d . . C52L C 0.4527(11) 0.2705(10) 0.9042(5) 0.061(3) Uani 1 d . . C51L C 0.4989(14) 0.3210(14) 0.9512(4) 0.084(4) Uani 1 d . . H1 H -0.0461 0.3186 0.8400 0.050 Uiso 1 d . . H2 H -0.2045 0.3477 0.7800 0.050 Uiso 1 d . . H3 H -0.0888 0.3361 0.7000 0.050 Uiso 1 d . . H4 H -0.0848 0.5312 0.7400 0.050 Uiso 1 d . . H5 H 0.0706 0.4985 0.8100 0.050 Uiso 1 d . . H6 H 0.2010 0.2845 0.8100 0.050 Uiso 1 d . . H71 H 0.1713 0.2963 0.7200 0.050 Uiso 1 d . . H72 H 0.0868 0.1894 0.7400 0.050 Uiso 1 d . . H811 H -0.4061 0.2035 0.7600 0.050 Uiso 1 d . . H812 H -0.3763 0.0737 0.7917 0.050 Uiso 1 d . . H813 H -0.3462 0.2110 0.8170 0.050 Uiso 1 d . . H821 H -0.1076 0.1022 0.7000 0.050 Uiso 1 d . . H822 H -0.2573 0.1520 0.6900 0.050 Uiso 1 d . . H823 H -0.2437 0.0227 0.7100 0.050 Uiso 1 d . . H911 H 0.3200 0.7026 0.7800 0.050 Uiso 1 d . . H912 H 0.2658 0.6522 0.8200 0.050 Uiso 1 d . . H913 H 0.1588 0.7219 0.7900 0.050 Uiso 1 d . . H921 H 0.3922 0.4520 0.8100 0.050 Uiso 1 d . . H922 H 0.3739 0.3736 0.7600 0.050 Uiso 1 d . . H923 H 0.4591 0.5068 0.7620 0.050 Uiso 1 d . . H12 H 0.0374 0.5191 0.5458 0.050 Uiso 1 d . . H14 H -0.1709 0.8058 0.6161 0.050 Uiso 1 d . . H18 H 0.0770 0.0779 0.9800 0.050 Uiso 1 d . . H20 H 0.3361 -0.0849 0.8789 0.050 Uiso 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 Sb1 0.0219(4) 0.0246(3) 0.0469(3) -0.0043(2) 0.0055(2) -0.0023(2) Cl11 0.0239(12) 0.0596(13) 0.0645(13) 0.0025(10) 0.0101(9) -0.0043(9) Cl12 0.0270(14) 0.0602(14) 0.094(2) 0.0076(12) 0.0136(11) -0.0116(10) Cl13 0.082(2) 0.0287(11) 0.128(3) 0.0026(13) 0.035(2) 0.0069(11) Cl14 0.088(2) 0.0254(11) 0.204(4) -0.016(2) 0.080(2) 0.0022(12) Cl15 0.050(2) 0.119(2) 0.061(2) 0.0178(15) -0.0102(12) -0.010(2) Cl16 0.063(2) 0.173(4) 0.0487(15) -0.001(2) 0.0019(12) -0.049(2) Sb2 0.0199(3) 0.0249(3) 0.0461(3) -0.0030(2) 0.0035(2) -0.0015(2) Cl21 0.0387(14) 0.0346(11) 0.109(2) -0.0192(11) -0.0173(12) -0.0007(9) Cl22 0.051(2) 0.0366(11) 0.099(2) -0.0245(11) 0.0165(12) -0.0138(10) Cl23 0.0236(13) 0.0607(14) 0.095(2) -0.0013(12) 0.0188(11) 0.0027(10) Cl24 0.051(2) 0.074(2) 0.073(2) 0.0246(13) -0.0178(12) -0.0069(12) Cl25 0.0303(14) 0.081(2) 0.088(2) -0.0379(14) 0.0219(11) -0.0069(11) Cl26 0.079(2) 0.074(2) 0.067(2) 0.0268(13) -0.0075(13) -0.0066(14) Cl31 0.0476(14) 0.0341(10) 0.0505(12) 0.0006(8) 0.0085(9) 0.0158(9) Cl32 0.067(2) 0.0595(14) 0.0639(15) 0.0272(11) -0.0257(12) -0.0099(12) Cl33 0.070(2) 0.0279(10) 0.0687(14) 0.0088(9) 0.0261(12) 0.0203(10) Cl41 0.0505(14) 0.0354(10) 0.0595(13) 0.0028(9) 0.0260(10) 0.0083(9) Cl42 0.078(2) 0.0619(15) 0.0561(14) 0.0116(11) -0.0254(12) 0.0062(13) Cl43 0.0550(14) 0.0324(9) 0.0417(11) -0.0005(7) 0.0096(9) 0.0198(9) N1 0.016(4) 0.018(3) 0.047(4) 0.001(2) 0.004(3) 0.002(2) N2 0.025(4) 0.022(3) 0.047(4) 0.001(2) 0.004(3) -0.001(2) N3 0.031(4) 0.014(3) 0.030(3) -0.001(2) 0.005(2) 0.002(2) N4 0.020(4) 0.019(3) 0.050(4) -0.001(2) 0.001(3) -0.003(2) C1 0.023(4) 0.012(3) 0.045(4) 0.002(3) 0.004(3) 0.001(3) C2 0.012(4) 0.016(3) 0.048(4) 0.000(3) 0.002(3) 0.000(3) C3 0.022(4) 0.014(3) 0.045(4) 0.000(3) -0.001(3) -0.003(3) C4 0.022(4) 0.013(3) 0.040(4) 0.001(3) 0.004(3) 0.000(3) C5 0.030(5) 0.012(3) 0.046(4) 0.000(3) 0.003(3) -0.004(3) C6 0.022(4) 0.018(3) 0.028(3) 0.000(2) 0.003(3) 0.002(3) C7 0.021(4) 0.016(3) 0.035(4) -0.001(3) 0.003(3) -0.004(3) C8 0.015(4) 0.019(3) 0.056(5) 0.003(3) 0.000(3) -0.003(3) C81 0.026(5) 0.039(4) 0.056(5) 0.003(3) 0.011(4) -0.001(3) C82 0.035(5) 0.025(4) 0.051(5) -0.004(3) -0.004(3) -0.009(3) C9 0.022(4) 0.026(4) 0.042(4) 0.003(3) -0.002(3) -0.006(3) C91 0.045(6) 0.027(4) 0.056(5) -0.001(3) 0.004(4) -0.013(3) C92 0.022(5) 0.043(4) 0.059(5) 0.005(4) 0.002(3) -0.009(3) C10 0.020(4) 0.023(3) 0.040(4) 0.006(3) 0.003(3) -0.007(3) C11 0.018(4) 0.022(3) 0.052(5) 0.003(3) 0.002(3) -0.002(3) C12 0.031(5) 0.034(4) 0.040(4) 0.008(3) -0.004(3) -0.015(3) C13 0.033(5) 0.037(4) 0.046(5) 0.012(3) -0.009(3) -0.011(3) C14 0.024(5) 0.029(4) 0.066(6) 0.018(4) 0.000(4) -0.001(3) C15 0.027(5) 0.024(4) 0.059(5) 0.012(3) 0.009(3) 0.000(3) C16 0.030(4) 0.015(3) 0.035(4) 0.003(3) 0.000(3) -0.002(3) C17 0.033(5) 0.018(3) 0.049(5) 0.002(3) 0.010(3) -0.002(3) C18 0.062(6) 0.027(4) 0.034(4) 0.005(3) 0.006(4) -0.009(4) C19 0.046(5) 0.022(3) 0.048(5) 0.007(3) -0.010(4) -0.006(3) C20 0.034(5) 0.020(3) 0.050(5) 0.003(3) -0.004(3) 0.001(3) C21 0.032(5) 0.017(3) 0.040(4) 0.000(3) 0.003(3) 0.001(3) N11L 0.084(8) 0.090(8) 0.080(7) -0.010(6) -0.006(5) -0.015(6) C12L 0.049(7) 0.075(7) 0.060(6) 0.006(5) -0.005(5) -0.025(5) C11L 0.061(8) 0.074(8) 0.103(9) -0.015(6) 0.023(6) -0.018(6) N22L 0.075(7) 0.068(6) 0.071(6) -0.013(5) -0.009(5) 0.004(5) C22L 0.027(5) 0.070(6) 0.053(5) 0.001(5) -0.005(4) -0.001(4) C21L 0.053(7) 0.077(7) 0.073(7) -0.024(5) -0.004(5) -0.001(5) N33L 0.088(9) 0.048(6) 0.095(9) -0.012(5) 0.044(7) -0.032(6) C32L 0.082(9) 0.072(7) 0.054(6) -0.013(5) 0.012(5) 0.009(7) C31L 0.047(7) 0.073(7) 0.107(9) 0.006(6) 0.012(6) -0.023(6) N44L 0.051(6) 0.103(8) 0.086(7) 0.004(6) 0.008(5) 0.030(5) C42L 0.035(6) 0.056(6) 0.065(6) -0.002(4) 0.000(4) 0.014(4) C41L 0.072(9) 0.115(11) 0.080(8) 0.022(7) -0.014(6) -0.004(8) N55L 0.070(7) 0.073(7) 0.093(8) 0.001(6) 0.013(6) -0.004(5) C52L 0.034(6) 0.055(6) 0.095(9) 0.029(6) 0.014(5) 0.011(4) C51L 0.076(9) 0.114(10) 0.062(7) 0.021(7) -0.006(6) 0.006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Cl16 2.324(3) . ? Sb1 Cl13 2.345(2) . ? Sb1 Cl14 2.352(3) . ? Sb1 Cl15 2.359(3) . ? Sb1 Cl12 2.362(2) . ? Sb1 Cl11 2.373(2) . ? Sb2 Cl26 2.351(3) . ? Sb2 Cl22 2.352(2) . ? Sb2 Cl24 2.355(3) . ? Sb2 Cl25 2.357(2) . ? Sb2 Cl21 2.363(2) . ? Sb2 Cl23 2.363(2) . ? Cl31 C11 1.729(7) . ? Cl32 C13 1.722(8) . ? Cl33 C15 1.729(9) . ? Cl41 C17 1.719(8) . ? Cl42 C19 1.737(8) . ? Cl43 C21 1.716(7) . ? N1 N2 1.240(9) . ? N1 C10 1.440(9) . ? N1 C4 1.497(9) . ? N2 C9 1.479(10) . ? N3 N4 1.243(8) . ? N3 C16 1.445(9) . ? N3 C1 1.496(8) . ? N4 C8 1.478(9) . ? C1 C6 1.533(10) . ? C1 C2 1.540(10) . ? C2 C3 1.533(10) . ? C2 C8 1.568(9) . ? C3 C7 1.527(10) . ? C3 C4 1.552(9) . ? C4 C5 1.526(10) . ? C5 C6 1.540(8) . ? C5 C9 1.559(10) . ? C6 C7 1.525(9) . ? C8 C82 1.510(11) . ? C8 C81 1.542(11) . ? C9 C92 1.524(11) . ? C9 C91 1.533(10) . ? C10 C11 1.388(10) . ? C10 C15 1.396(10) . ? C11 C12 1.364(11) . ? C12 C13 1.374(12) . ? C13 C14 1.389(12) . ? C14 C15 1.359(11) . ? C16 C21 1.389(10) . ? C16 C17 1.394(10) . ? C17 C18 1.382(11) . ? C18 C19 1.378(12) . ? C19 C20 1.372(12) . ? C20 C21 1.380(11) . ? N11L C12L 1.140(15) . ? C12L C11L 1.44(2) . ? N22L C22L 1.134(13) . ? C22L C21L 1.451(14) . ? N33L C32L 1.102(15) . ? C32L C31L 1.48(2) . ? N44L C42L 1.131(13) . ? C42L C41L 1.42(2) . ? N55L C52L 1.146(15) . ? C52L C51L 1.46(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 Cl16 Sb1 Cl13 89.66(15) . . ? Cl16 Sb1 Cl14 90.9(2) . . ? Cl13 Sb1 Cl14 178.59(10) . . ? Cl16 Sb1 Cl15 179.39(13) . . ? Cl13 Sb1 Cl15 89.79(13) . . ? Cl14 Sb1 Cl15 89.64(15) . . ? Cl16 Sb1 Cl12 90.11(10) . . ? Cl13 Sb1 Cl12 91.18(10) . . ? Cl14 Sb1 Cl12 90.10(10) . . ? Cl15 Sb1 Cl12 89.64(10) . . ? Cl16 Sb1 Cl11 91.80(10) . . ? Cl13 Sb1 Cl11 90.17(9) . . ? Cl14 Sb1 Cl11 88.52(10) . . ? Cl15 Sb1 Cl11 88.47(9) . . ? Cl12 Sb1 Cl11 177.67(8) . . ? Cl26 Sb2 Cl22 91.39(11) . . ? Cl26 Sb2 Cl24 178.93(10) . . ? Cl22 Sb2 Cl24 89.25(11) . . ? Cl26 Sb2 Cl25 91.01(11) . . ? Cl22 Sb2 Cl25 88.88(9) . . ? Cl24 Sb2 Cl25 89.86(11) . . ? Cl26 Sb2 Cl21 89.96(10) . . ? Cl22 Sb2 Cl21 178.48(9) . . ? Cl24 Sb2 Cl21 89.42(10) . . ? Cl25 Sb2 Cl21 90.39(9) . . ? Cl26 Sb2 Cl23 89.48(11) . . ? Cl22 Sb2 Cl23 90.78(9) . . ? Cl24 Sb2 Cl23 89.65(10) . . ? Cl25 Sb2 Cl23 179.41(10) . . ? Cl21 Sb2 Cl23 89.93(10) . . ? N2 N1 C10 119.3(6) . . ? N2 N1 C4 116.6(6) . . ? C10 N1 C4 124.0(6) . . ? N1 N2 C9 110.3(6) . . ? N4 N3 C16 121.5(5) . . ? N4 N3 C1 117.3(6) . . ? C16 N3 C1 121.2(5) . . ? N3 N4 C8 110.1(5) . . ? N3 C1 C6 111.6(5) . . ? N3 C1 C2 102.4(5) . . ? C6 C1 C2 105.3(5) . . ? C3 C2 C1 101.9(5) . . ? C3 C2 C8 116.5(6) . . ? C1 C2 C8 103.6(5) . . ? C2 C3 C7 103.9(5) . . ? C2 C3 C4 102.9(5) . . ? C7 C3 C4 100.7(5) . . ? N1 C4 C5 102.8(6) . . ? N1 C4 C3 111.9(5) . . ? C5 C4 C3 104.8(5) . . ? C4 C5 C6 102.8(5) . . ? C4 C5 C9 104.0(6) . . ? C6 C5 C9 116.0(6) . . ? C1 C6 C7 102.0(5) . . ? C1 C6 C5 102.6(5) . . ? C7 C6 C5 102.5(5) . . ? C6 C7 C3 95.7(5) . . ? N4 C8 C82 109.1(6) . . ? N4 C8 C81 102.5(6) . . ? C82 C8 C81 110.9(6) . . ? N4 C8 C2 105.9(5) . . ? C82 C8 C2 117.0(6) . . ? C81 C8 C2 110.3(6) . . ? N2 C9 C92 109.6(6) . . ? N2 C9 C91 101.7(6) . . ? C92 C9 C91 110.9(6) . . ? N2 C9 C5 105.5(6) . . ? C92 C9 C5 117.2(6) . . ? C91 C9 C5 110.7(6) . . ? C11 C10 C15 119.7(7) . . ? C11 C10 N1 122.0(6) . . ? C15 C10 N1 118.2(6) . . ? C12 C11 C10 120.1(7) . . ? C12 C11 Cl31 120.2(6) . . ? C10 C11 Cl31 119.7(6) . . ? C13 C12 C11 119.2(7) . . ? C12 C13 C14 122.0(7) . . ? C12 C13 Cl32 119.5(7) . . ? C14 C13 Cl32 118.5(6) . . ? C15 C14 C13 118.4(7) . . ? C14 C15 C10 120.6(8) . . ? C14 C15 Cl33 119.6(6) . . ? C10 C15 Cl33 119.8(6) . . ? C21 C16 C17 119.9(6) . . ? C21 C16 N3 121.3(6) . . ? C17 C16 N3 118.7(6) . . ? C18 C17 C16 120.3(7) . . ? C18 C17 Cl41 120.1(6) . . ? C16 C17 Cl41 119.6(6) . . ? C19 C18 C17 117.9(7) . . ? C18 C19 C20 123.3(7) . . ? C18 C19 Cl42 117.7(6) . . ? C20 C19 Cl42 118.9(7) . . ? C21 C20 C19 118.3(7) . . ? C20 C21 C16 120.2(7) . . ? C20 C21 Cl43 118.9(6) . . ? C16 C21 Cl43 120.9(5) . . ? N11L C12L C11L 178.1(13) . . ? N22L C22L C21L 178.5(11) . . ? N33L C32L C31L 178.8(12) . . ? N44L C42L C41L 177.6(12) . . ? N55L C52L C51L 179.8(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 N2 C9 171.7(5) . . . . ? C4 N1 N2 C9 -6.8(8) . . . . ? C16 N3 N4 C8 174.7(6) . . . . ? C1 N3 N4 C8 -5.7(8) . . . . ? N4 N3 C1 C6 -111.7(7) . . . . ? C16 N3 C1 C6 67.9(8) . . . . ? N4 N3 C1 C2 0.5(8) . . . . ? C16 N3 C1 C2 -179.9(6) . . . . ? N3 C1 C2 C3 -116.8(5) . . . . ? C6 C1 C2 C3 0.0(6) . . . . ? N3 C1 C2 C8 4.5(7) . . . . ? C6 C1 C2 C8 121.3(5) . . . . ? C1 C2 C3 C7 33.2(6) . . . . ? C8 C2 C3 C7 -78.7(7) . . . . ? C1 C2 C3 C4 -71.4(6) . . . . ? C8 C2 C3 C4 176.7(5) . . . . ? N2 N1 C4 C5 1.1(7) . . . . ? C10 N1 C4 C5 -177.3(6) . . . . ? N2 N1 C4 C3 -110.8(7) . . . . ? C10 N1 C4 C3 70.8(8) . . . . ? C2 C3 C4 N1 -176.4(5) . . . . ? C7 C3 C4 N1 76.5(6) . . . . ? C2 C3 C4 C5 73.0(6) . . . . ? C7 C3 C4 C5 -34.1(7) . . . . ? N1 C4 C5 C6 -116.8(5) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? N1 C4 C5 C9 4.6(6) . . . . ? C3 C4 C5 C9 121.6(6) . . . . ? N3 C1 C6 C7 77.5(6) . . . . ? C2 C1 C6 C7 -32.9(6) . . . . ? N3 C1 C6 C5 -176.7(5) . . . . ? C2 C1 C6 C5 73.0(6) . . . . ? C4 C5 C6 C1 -71.6(6) . . . . ? C9 C5 C6 C1 175.7(6) . . . . ? C4 C5 C6 C7 33.9(7) . . . . ? C9 C5 C6 C7 -78.8(7) . . . . ? C1 C6 C7 C3 51.5(5) . . . . ? C5 C6 C7 C3 -54.5(6) . . . . ? C2 C3 C7 C6 -52.8(6) . . . . ? C4 C3 C7 C6 53.5(6) . . . . ? N3 N4 C8 C82 135.1(6) . . . . ? N3 N4 C8 C81 -107.3(6) . . . . ? N3 N4 C8 C2 8.3(8) . . . . ? C3 C2 C8 N4 103.4(7) . . . . ? C1 C2 C8 N4 -7.5(7) . . . . ? C3 C2 C8 C82 -18.5(9) . . . . ? C1 C2 C8 C82 -129.4(7) . . . . ? C3 C2 C8 C81 -146.4(6) . . . . ? C1 C2 C8 C81 102.6(7) . . . . ? N1 N2 C9 C92 136.3(6) . . . . ? N1 N2 C9 C91 -106.3(6) . . . . ? N1 N2 C9 C5 9.3(7) . . . . ? C4 C5 C9 N2 -8.1(7) . . . . ? C6 C5 C9 N2 103.9(7) . . . . ? C4 C5 C9 C92 -130.4(6) . . . . ? C6 C5 C9 C92 -18.4(9) . . . . ? C4 C5 C9 C91 101.2(7) . . . . ? C6 C5 C9 C91 -146.8(6) . . . . ? N2 N1 C10 C11 72.1(8) . . . . ? C4 N1 C10 C11 -109.5(8) . . . . ? N2 N1 C10 C15 -104.5(8) . . . . ? C4 N1 C10 C15 73.9(8) . . . . ? C15 C10 C11 C12 -1.2(10) . . . . ? N1 C10 C11 C12 -177.8(6) . . . . ? C15 C10 C11 Cl31 178.2(6) . . . . ? N1 C10 C11 Cl31 1.7(9) . . . . ? C10 C11 C12 C13 1.0(11) . . . . ? Cl31 C11 C12 C13 -178.4(6) . . . . ? C11 C12 C13 C14 -0.6(11) . . . . ? C11 C12 C13 Cl32 177.5(6) . . . . ? C12 C13 C14 C15 0.5(12) . . . . ? Cl32 C13 C14 C15 -177.7(6) . . . . ? C13 C14 C15 C10 -0.7(11) . . . . ? C13 C14 C15 Cl33 177.9(6) . . . . ? C11 C10 C15 C14 1.0(11) . . . . ? N1 C10 C15 C14 177.7(7) . . . . ? C11 C10 C15 Cl33 -177.5(6) . . . . ? N1 C10 C15 Cl33 -0.8(9) . . . . ? N4 N3 C16 C21 75.2(9) . . . . ? C1 N3 C16 C21 -104.4(7) . . . . ? N4 N3 C16 C17 -106.7(7) . . . . ? C1 N3 C16 C17 73.7(8) . . . . ? C21 C16 C17 C18 1.0(10) . . . . ? N3 C16 C17 C18 -177.1(6) . . . . ? C21 C16 C17 Cl41 -178.8(5) . . . . ? N3 C16 C17 Cl41 3.1(9) . . . . ? C16 C17 C18 C19 0.4(11) . . . . ? Cl41 C17 C18 C19 -179.8(6) . . . . ? C17 C18 C19 C20 -2.1(12) . . . . ? C17 C18 C19 Cl42 177.6(6) . . . . ? C18 C19 C20 C21 2.3(11) . . . . ? Cl42 C19 C20 C21 -177.5(6) . . . . ? C19 C20 C21 C16 -0.7(10) . . . . ? C19 C20 C21 Cl43 177.8(6) . . . . ? C17 C16 C21 C20 -0.9(10) . . . . ? N3 C16 C21 C20 177.2(6) . . . . ? C17 C16 C21 Cl43 -179.4(5) . . . . ? N3 C16 C21 Cl43 -1.3(9) . . . . ? _refine_diff_density_max 2.885 _refine_diff_density_min -1.924 _refine_diff_density_rms 0.172