# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Cristian Silvestru' _publ_contact_author_email CRISTI@CHEM.UBBCLUJ.RO _publ_section_title ; New chiral organoantimony(III) compounds containing intramolecular N?Sb interactions - solution behaviour and solid state structures ; _publ_author_address 'Arany Janos No11, Cluj-Napoca, 400028, Romania' _publ_contact_author_address 'Arany Janos No11, Cluj-Napoca, 400028, Romania' loop_ _publ_author_name 'Cristian Silvestru' 'Vilma R. Bojan' 'Hans J Breunig' 'Dana Copolovici' 'Ciprian Rat' ; A.Silvestru ; # Attachment 'Compound 7 - CCDC - 752086.cif' data_137rich _database_code_depnum_ccdc_archive 'CCDC 752086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 Br N Sb' _chemical_formula_sum 'C18 H23 Br N Sb' _chemical_formula_weight 455.03 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 8.8931(5) _cell_length_b 9.5876(6) _cell_length_c 21.2914(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.2650(10) _cell_angle_gamma 90.00 _cell_volume 1791.70(19) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6781 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 3.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.276 _exptl_absorpt_correction_T_max 0.3895 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13934 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3656 _reflns_number_gt 3419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0358P)^2^+3.4761P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3656 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.36779(6) 0.55410(5) 0.15409(2) 0.05202(15) Uani 1 1 d . . . C1 C 0.5408(5) 0.2198(5) 0.1601(2) 0.0382(9) Uani 1 1 d . . . C2 C 0.5766(5) 0.0844(5) 0.1445(2) 0.0450(10) Uani 1 1 d . . . C3 C 0.7253(6) 0.0358(6) 0.1612(3) 0.0607(14) Uani 1 1 d . . . H3 H 0.7494 -0.0546 0.1505 0.073 Uiso 1 1 calc R . . C4 C 0.8360(6) 0.1198(7) 0.1931(3) 0.0624(15) Uani 1 1 d . . . H4 H 0.9346 0.0860 0.2043 0.075 Uiso 1 1 calc R . . C5 C 0.8027(6) 0.2532(6) 0.2087(2) 0.0563(13) Uani 1 1 d . . . H5 H 0.8789 0.3099 0.2303 0.068 Uiso 1 1 calc R . . C6 C 0.6556(5) 0.3042(5) 0.1926(2) 0.0452(11) Uani 1 1 d . . . H6 H 0.6334 0.3950 0.2034 0.054 Uiso 1 1 calc R . . C7 C 0.4548(6) -0.0038(5) 0.1071(3) 0.0565(13) Uani 1 1 d . . . H7A H 0.4494 0.0157 0.0621 0.068 Uiso 1 1 calc R . . H7B H 0.4804 -0.1015 0.1141 0.068 Uiso 1 1 calc R . . C8 C 0.2997(7) -0.0379(6) 0.1895(3) 0.0650(15) Uani 1 1 d . . . H8A H 0.2039 -0.0154 0.2024 0.097 Uiso 1 1 calc R . . H8B H 0.3813 -0.0012 0.2200 0.097 Uiso 1 1 calc R . . H8C H 0.3097 -0.1374 0.1872 0.097 Uiso 1 1 calc R . . C9 C 0.1817(8) -0.0310(6) 0.0798(3) 0.0777(19) Uani 1 1 d . . . H9A H 0.1817 0.0139 0.0395 0.117 Uiso 1 1 calc R . . H9B H 0.0865 -0.0137 0.0941 0.117 Uiso 1 1 calc R . . H9C H 0.1951 -0.1297 0.0752 0.117 Uiso 1 1 calc R . . C10 C 0.2462(4) 0.3032(4) 0.04085(18) 0.0313(8) Uani 1 1 d . . . C11 C 0.3501(5) 0.3161(4) -0.00225(19) 0.0340(8) Uani 1 1 d . . . C12 C 0.2928(5) 0.3314(5) -0.06664(19) 0.0392(9) Uani 1 1 d . . . H12 H 0.3611 0.3367 -0.0953 0.047 Uiso 1 1 calc R . . C13 C 0.1387(5) 0.3392(5) -0.08972(19) 0.0397(9) Uani 1 1 d . . . C14 C 0.0391(5) 0.3317(5) -0.0462(2) 0.0386(9) Uani 1 1 d . . . H14 H -0.0648 0.3400 -0.0608 0.046 Uiso 1 1 calc R . . C15 C 0.0888(4) 0.3122(4) 0.01799(19) 0.0334(8) Uani 1 1 d . . . C16 C 0.5201(5) 0.3197(6) 0.0171(2) 0.0459(11) Uani 1 1 d . . . H16A H 0.5667 0.3476 -0.0186 0.069 Uiso 1 1 calc R . . H16B H 0.5560 0.2286 0.0309 0.069 Uiso 1 1 calc R . . H16C H 0.5464 0.3851 0.0512 0.069 Uiso 1 1 calc R . . C17 C 0.0808(6) 0.3577(6) -0.1595(2) 0.0585(13) Uani 1 1 d . . . H17A H 0.0390 0.2712 -0.1771 0.088 Uiso 1 1 calc R . . H17B H 0.1633 0.3855 -0.1808 0.088 Uiso 1 1 calc R . . H17C H 0.0031 0.4282 -0.1652 0.088 Uiso 1 1 calc R . . C18 C -0.0319(5) 0.3033(5) 0.0603(2) 0.0473(11) Uani 1 1 d . . . H18A H -0.1292 0.3274 0.0363 0.071 Uiso 1 1 calc R . . H18B H -0.0075 0.3668 0.0954 0.071 Uiso 1 1 calc R . . H18C H -0.0357 0.2099 0.0763 0.071 Uiso 1 1 calc R . . N1 N 0.3059(5) 0.0241(4) 0.12610(19) 0.0463(9) Uani 1 1 d . . . Sb1 Sb 0.30467(3) 0.27872(3) 0.143048(12) 0.03359(10) 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 Br1 0.0576(3) 0.0418(3) 0.0562(3) -0.0052(2) 0.0079(2) -0.0003(2) C1 0.039(2) 0.041(2) 0.033(2) 0.0051(18) 0.0014(17) -0.0015(18) C2 0.052(3) 0.040(3) 0.044(2) 0.005(2) 0.012(2) 0.004(2) C3 0.060(3) 0.055(3) 0.071(4) 0.016(3) 0.022(3) 0.022(3) C4 0.044(3) 0.084(4) 0.060(3) 0.027(3) 0.011(2) 0.017(3) C5 0.042(3) 0.078(4) 0.046(3) 0.012(3) -0.001(2) -0.004(2) C6 0.044(2) 0.052(3) 0.038(2) 0.003(2) 0.0016(19) -0.002(2) C7 0.067(3) 0.040(3) 0.065(3) -0.005(2) 0.019(3) 0.003(2) C8 0.071(4) 0.049(3) 0.076(4) 0.016(3) 0.016(3) -0.001(3) C9 0.087(4) 0.045(3) 0.091(5) -0.013(3) -0.015(4) -0.016(3) C10 0.034(2) 0.029(2) 0.0304(19) -0.0016(15) 0.0034(15) -0.0026(15) C11 0.033(2) 0.034(2) 0.036(2) -0.0001(17) 0.0065(16) -0.0009(16) C12 0.043(2) 0.042(2) 0.034(2) -0.0049(18) 0.0103(17) 0.0007(19) C13 0.050(2) 0.035(2) 0.032(2) -0.0016(18) 0.0005(18) -0.0011(19) C14 0.034(2) 0.037(2) 0.042(2) -0.0019(19) -0.0020(17) -0.0029(17) C15 0.032(2) 0.031(2) 0.037(2) -0.0027(17) 0.0058(16) -0.0042(16) C16 0.035(2) 0.061(3) 0.042(2) 0.010(2) 0.0080(18) 0.000(2) C17 0.064(3) 0.074(4) 0.034(2) -0.002(2) 0.000(2) 0.007(3) C18 0.036(2) 0.062(3) 0.045(2) 0.004(2) 0.0099(19) -0.001(2) N1 0.057(2) 0.0282(19) 0.052(2) -0.0003(16) 0.0024(18) -0.0045(16) Sb1 0.03493(16) 0.03643(17) 0.02935(15) -0.00050(11) 0.00498(10) -0.00093(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Sb1 2.7016(6) . ? C1 C2 1.390(6) . ? C1 C6 1.395(6) . ? C1 Sb1 2.149(4) . ? C2 C3 1.394(7) . ? C2 C7 1.498(7) . ? C3 C4 1.364(8) . ? C3 H3 0.9300 . ? C4 C5 1.366(8) . ? C4 H4 0.9300 . ? C5 C6 1.387(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.470(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.485(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.456(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.408(6) . ? C10 C15 1.409(6) . ? C10 Sb1 2.167(4) . ? C11 C12 1.391(6) . ? C11 C16 1.502(6) . ? C12 C13 1.381(6) . ? C12 H12 0.9300 . ? C13 C14 1.382(6) . ? C13 C17 1.503(6) . ? C14 C15 1.380(6) . ? C14 H14 0.9300 . ? C15 C18 1.511(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 Sb1 2.468(4) . ? 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 C2 C1 C6 118.9(4) . . ? C2 C1 Sb1 117.4(3) . . ? C6 C1 Sb1 123.3(3) . . ? C1 C2 C3 119.7(5) . . ? C1 C2 C7 118.7(4) . . ? C3 C2 C7 121.5(5) . . ? C4 C3 C2 120.6(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.4(5) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.2(5) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N1 C7 C2 111.0(4) . . ? N1 C7 H7A 109.4 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C2 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 119.3(4) . . ? C11 C10 Sb1 126.0(3) . . ? C15 C10 Sb1 114.7(3) . . ? C12 C11 C10 118.5(4) . . ? C12 C11 C16 117.4(4) . . ? C10 C11 C16 124.1(4) . . ? C13 C12 C11 122.8(4) . . ? C13 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? C12 C13 C14 117.7(4) . . ? C12 C13 C17 121.4(4) . . ? C14 C13 C17 121.0(4) . . ? C15 C14 C13 122.3(4) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C10 119.5(4) . . ? C14 C15 C18 117.0(4) . . ? C10 C15 C18 123.5(4) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 N1 C7 111.5(5) . . ? C9 N1 C8 109.6(4) . . ? C7 N1 C8 110.1(4) . . ? C9 N1 Sb1 115.9(3) . . ? C7 N1 Sb1 104.2(3) . . ? C8 N1 Sb1 105.2(3) . . ? C1 Sb1 C10 105.55(15) . . ? C1 Sb1 N1 74.79(15) . . ? C10 Sb1 N1 88.06(14) . . ? C1 Sb1 Br1 93.35(12) . . ? C10 Sb1 Br1 89.69(10) . . ? N1 Sb1 Br1 166.82(10) . . ? 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 C6 C1 C2 C3 -0.2(7) . . . . ? Sb1 C1 C2 C3 -172.7(4) . . . . ? C6 C1 C2 C7 -177.3(4) . . . . ? Sb1 C1 C2 C7 10.1(6) . . . . ? C1 C2 C3 C4 0.4(8) . . . . ? C7 C2 C3 C4 177.5(5) . . . . ? C2 C3 C4 C5 -0.5(8) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C2 C1 C6 C5 0.1(7) . . . . ? Sb1 C1 C6 C5 172.1(4) . . . . ? C1 C2 C7 N1 -36.4(6) . . . . ? C3 C2 C7 N1 146.5(5) . . . . ? C15 C10 C11 C12 -2.7(6) . . . . ? Sb1 C10 C11 C12 -179.8(3) . . . . ? C15 C10 C11 C16 174.9(4) . . . . ? Sb1 C10 C11 C16 -2.2(6) . . . . ? C10 C11 C12 C13 2.2(7) . . . . ? C16 C11 C12 C13 -175.6(4) . . . . ? C11 C12 C13 C14 0.2(7) . . . . ? C11 C12 C13 C17 179.2(4) . . . . ? C12 C13 C14 C15 -2.2(7) . . . . ? C17 C13 C14 C15 178.8(4) . . . . ? C13 C14 C15 C10 1.6(6) . . . . ? C13 C14 C15 C18 -178.9(4) . . . . ? C11 C10 C15 C14 0.9(6) . . . . ? Sb1 C10 C15 C14 178.3(3) . . . . ? C11 C10 C15 C18 -178.5(4) . . . . ? Sb1 C10 C15 C18 -1.1(5) . . . . ? C2 C7 N1 C9 164.7(4) . . . . ? C2 C7 N1 C8 -73.4(5) . . . . ? C2 C7 N1 Sb1 38.9(5) . . . . ? C2 C1 Sb1 C10 -74.0(4) . . . . ? C6 C1 Sb1 C10 113.8(4) . . . . ? C2 C1 Sb1 N1 9.6(3) . . . . ? C6 C1 Sb1 N1 -162.6(4) . . . . ? C2 C1 Sb1 Br1 -164.6(3) . . . . ? C6 C1 Sb1 Br1 23.2(4) . . . . ? C11 C10 Sb1 C1 -15.9(4) . . . . ? C15 C10 Sb1 C1 166.9(3) . . . . ? C11 C10 Sb1 N1 -89.5(4) . . . . ? C15 C10 Sb1 N1 93.3(3) . . . . ? C11 C10 Sb1 Br1 77.5(3) . . . . ? C15 C10 Sb1 Br1 -99.7(3) . . . . ? C9 N1 Sb1 C1 -149.5(4) . . . . ? C7 N1 Sb1 C1 -26.6(3) . . . . ? C8 N1 Sb1 C1 89.3(3) . . . . ? C9 N1 Sb1 C10 -42.8(4) . . . . ? C7 N1 Sb1 C10 80.1(3) . . . . ? C8 N1 Sb1 C10 -164.0(3) . . . . ? C9 N1 Sb1 Br1 -123.1(5) . . . . ? C7 N1 Sb1 Br1 -0.2(6) . . . . ? C8 N1 Sb1 Br1 115.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.881 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.093 # Attachment 'Compound 5 - CCDC - 752087.cif' data_150rich _database_code_depnum_ccdc_archive 'CCDC 752087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H29 N2 Sb' _chemical_formula_sum 'C24 H29 N2 Sb' _chemical_formula_weight 467.24 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7366(6) _cell_length_b 16.1565(11) _cell_length_c 16.1689(11) _cell_angle_alpha 88.2760(10) _cell_angle_beta 89.6180(10) _cell_angle_gamma 82.7230(10) _cell_volume 2262.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4018 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 21.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7737 _exptl_absorpt_correction_T_max 0.8974 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22113 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0566 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7962 _reflns_number_gt 6442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0251P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7962 _refine_ls_number_parameters 495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4072(4) 0.3630(2) 0.7783(3) 0.0399(10) Uani 1 1 d . . . C2 C 0.4962(5) 0.4236(3) 0.7488(3) 0.0463(11) Uani 1 1 d . . . C3 C 0.5717(6) 0.4683(3) 0.8045(3) 0.0639(14) Uani 1 1 d . . . H3 H 0.6319 0.5080 0.7844 0.077 Uiso 1 1 calc R . . C4 C 0.5595(6) 0.4552(3) 0.8878(3) 0.0742(16) Uani 1 1 d . . . H4 H 0.6094 0.4867 0.9239 0.089 Uiso 1 1 calc R . . C5 C 0.4733(6) 0.3954(3) 0.9187(3) 0.0660(14) Uani 1 1 d . . . H5 H 0.4662 0.3852 0.9754 0.079 Uiso 1 1 calc R . . C6 C 0.3973(5) 0.3505(3) 0.8636(3) 0.0534(12) Uani 1 1 d . . . H6 H 0.3378 0.3108 0.8844 0.064 Uiso 1 1 calc R . . C7 C 0.5066(5) 0.4427(3) 0.6571(3) 0.0567(13) Uani 1 1 d . . . H7A H 0.4101 0.4737 0.6383 0.068 Uiso 1 1 calc R . . H7B H 0.5879 0.4775 0.6468 0.068 Uiso 1 1 calc R . . C8 C 0.6976(5) 0.3285(3) 0.6208(3) 0.0794(17) Uani 1 1 d . . . H8A H 0.7128 0.2760 0.5937 0.119 Uiso 1 1 calc R . . H8B H 0.7191 0.3196 0.6787 0.119 Uiso 1 1 calc R . . H8C H 0.7658 0.3649 0.5971 0.119 Uiso 1 1 calc R . . C9 C 0.5016(6) 0.3808(3) 0.5229(3) 0.0793(17) Uani 1 1 d . . . H9A H 0.5675 0.4184 0.4987 0.119 Uiso 1 1 calc R . . H9B H 0.3959 0.4050 0.5174 0.119 Uiso 1 1 calc R . . H9C H 0.5170 0.3288 0.4949 0.119 Uiso 1 1 calc R . . C10 C 0.4578(4) 0.1862(2) 0.6887(2) 0.0375(10) Uani 1 1 d . . . C11 C 0.4564(5) 0.1303(3) 0.6245(3) 0.0420(10) Uani 1 1 d . . . C12 C 0.5742(5) 0.0639(3) 0.6193(3) 0.0551(13) Uani 1 1 d . . . H12 H 0.5730 0.0264 0.5768 0.066 Uiso 1 1 calc R . . C13 C 0.6915(5) 0.0530(3) 0.6757(3) 0.0627(14) Uani 1 1 d . . . H13 H 0.7701 0.0089 0.6709 0.075 Uiso 1 1 calc R . . C14 C 0.6938(5) 0.1064(3) 0.7387(3) 0.0613(14) Uani 1 1 d . . . H14 H 0.7731 0.0985 0.7774 0.074 Uiso 1 1 calc R . . C15 C 0.5776(5) 0.1728(3) 0.7454(3) 0.0492(11) Uani 1 1 d . . . H15 H 0.5799 0.2091 0.7888 0.059 Uiso 1 1 calc R . . C16 C 0.3287(5) 0.1416(3) 0.5610(3) 0.0527(12) Uani 1 1 d . . . H16A H 0.3384 0.1909 0.5267 0.063 Uiso 1 1 calc R . . H16B H 0.3386 0.0938 0.5256 0.063 Uiso 1 1 calc R . . C17 C 0.0578(6) 0.1781(4) 0.5408(3) 0.0934(19) Uani 1 1 d . . . H17A H 0.0727 0.2323 0.5186 0.140 Uiso 1 1 calc R . . H17B H -0.0409 0.1811 0.5677 0.140 Uiso 1 1 calc R . . H17C H 0.0617 0.1393 0.4967 0.140 Uiso 1 1 calc R . . C18 C 0.1494(6) 0.0728(3) 0.6422(3) 0.0781(16) Uani 1 1 d . . . H18A H 0.1411 0.0310 0.6021 0.117 Uiso 1 1 calc R . . H18B H 0.0548 0.0823 0.6731 0.117 Uiso 1 1 calc R . . H18C H 0.2329 0.0541 0.6793 0.117 Uiso 1 1 calc R . . C19 C 0.1391(5) 0.2477(3) 0.7868(3) 0.0442(11) Uani 1 1 d . . . C20 C 0.1792(6) 0.1753(3) 0.8356(3) 0.0577(13) Uani 1 1 d . . . H20 H 0.2756 0.1445 0.8293 0.069 Uiso 1 1 calc R . . C21 C 0.0774(7) 0.1497(3) 0.8926(3) 0.0721(16) Uani 1 1 d . . . H21 H 0.1057 0.1021 0.9255 0.087 Uiso 1 1 calc R . . C22 C -0.0669(8) 0.1942(5) 0.9015(4) 0.090(2) Uani 1 1 d . . . H22 H -0.1364 0.1765 0.9399 0.108 Uiso 1 1 calc R . . C23 C -0.1069(6) 0.2640(4) 0.8538(4) 0.087(2) Uani 1 1 d . . . H23 H -0.2041 0.2941 0.8600 0.105 Uiso 1 1 calc R . . C24 C -0.0057(5) 0.2910(3) 0.7966(3) 0.0615(14) Uani 1 1 d . . . H24 H -0.0353 0.3388 0.7642 0.074 Uiso 1 1 calc R . . C25 C 0.1598(5) 0.3647(2) 0.2744(2) 0.0403(10) Uani 1 1 d . . . C26 C 0.0421(5) 0.4250(3) 0.2438(3) 0.0468(11) Uani 1 1 d . . . C27 C -0.0524(6) 0.4718(3) 0.2984(3) 0.0647(14) Uani 1 1 d . . . H27 H -0.1296 0.5118 0.2777 0.078 Uiso 1 1 calc R . . C28 C -0.0356(6) 0.4611(3) 0.3824(3) 0.0728(16) Uani 1 1 d . . . H28 H -0.1002 0.4935 0.4181 0.087 Uiso 1 1 calc R . . C29 C 0.0783(6) 0.4015(3) 0.4133(3) 0.0651(14) Uani 1 1 d . . . H29 H 0.0901 0.3928 0.4702 0.078 Uiso 1 1 calc R . . C30 C 0.1752(5) 0.3547(3) 0.3592(3) 0.0525(12) Uani 1 1 d . . . H30 H 0.2528 0.3153 0.3806 0.063 Uiso 1 1 calc R . . C31 C 0.0240(5) 0.4414(3) 0.1520(3) 0.0577(13) Uani 1 1 d . . . H31A H -0.0718 0.4775 0.1415 0.069 Uiso 1 1 calc R . . H31B H 0.1081 0.4703 0.1317 0.069 Uiso 1 1 calc R . . C32 C -0.1201(6) 0.3290(3) 0.1201(3) 0.0809(17) Uani 1 1 d . . . H32A H -0.1357 0.3200 0.1783 0.121 Uiso 1 1 calc R . . H32B H -0.1145 0.2768 0.0927 0.121 Uiso 1 1 calc R . . H32C H -0.2046 0.3668 0.0980 0.121 Uiso 1 1 calc R . . C33 C 0.0545(6) 0.3765(3) 0.0185(3) 0.0817(17) Uani 1 1 d . . . H33A H 0.0648 0.3235 -0.0076 0.122 Uiso 1 1 calc R . . H33B H 0.1485 0.4010 0.0117 0.122 Uiso 1 1 calc R . . H33C H -0.0291 0.4128 -0.0064 0.122 Uiso 1 1 calc R . . C34 C 0.1864(4) 0.1852(2) 0.1895(2) 0.0377(10) Uani 1 1 d . . . C35 C 0.2134(4) 0.1263(3) 0.1274(2) 0.0407(10) Uani 1 1 d . . . C36 C 0.1222(5) 0.0629(3) 0.1227(3) 0.0498(12) Uani 1 1 d . . . H36 H 0.1397 0.0245 0.0810 0.060 Uiso 1 1 calc R . . C37 C 0.0056(5) 0.0558(3) 0.1793(3) 0.0537(12) Uani 1 1 d . . . H37 H -0.0548 0.0126 0.1757 0.064 Uiso 1 1 calc R . . C38 C -0.0213(5) 0.1123(3) 0.2405(3) 0.0554(13) Uani 1 1 d . . . H38 H -0.1004 0.1078 0.2785 0.066 Uiso 1 1 calc R . . C39 C 0.0695(5) 0.1763(2) 0.2459(3) 0.0465(11) Uani 1 1 d . . . H39 H 0.0515 0.2140 0.2883 0.056 Uiso 1 1 calc R . . C40 C 0.3420(5) 0.1327(3) 0.0656(3) 0.0528(12) Uani 1 1 d . . . H40A H 0.3539 0.0834 0.0322 0.063 Uiso 1 1 calc R . . H40B H 0.3146 0.1809 0.0290 0.063 Uiso 1 1 calc R . . C41 C 0.6015(6) 0.1653(4) 0.0478(3) 0.097(2) Uani 1 1 d . . . H41A H 0.6259 0.1227 0.0080 0.145 Uiso 1 1 calc R . . H41B H 0.6932 0.1733 0.0773 0.145 Uiso 1 1 calc R . . H41C H 0.5611 0.2166 0.0198 0.145 Uiso 1 1 calc R . . C42 C 0.5454(6) 0.0633(3) 0.1499(3) 0.0787(17) Uani 1 1 d . . . H42A H 0.4706 0.0497 0.1901 0.118 Uiso 1 1 calc R . . H42B H 0.6399 0.0703 0.1773 0.118 Uiso 1 1 calc R . . H42C H 0.5643 0.0189 0.1115 0.118 Uiso 1 1 calc R . . C43 C 0.4789(4) 0.2491(3) 0.2828(2) 0.0411(10) Uani 1 1 d . . . C44 C 0.4813(5) 0.1760(3) 0.3298(3) 0.0575(13) Uani 1 1 d . . . H44 H 0.4045 0.1420 0.3225 0.069 Uiso 1 1 calc R . . C45 C 0.5955(6) 0.1527(4) 0.3874(3) 0.0729(15) Uani 1 1 d . . . H45 H 0.5944 0.1035 0.4186 0.087 Uiso 1 1 calc R . . C46 C 0.7092(6) 0.2009(4) 0.3990(3) 0.0750(17) Uani 1 1 d . . . H46 H 0.7862 0.1843 0.4377 0.090 Uiso 1 1 calc R . . C47 C 0.7111(6) 0.2736(4) 0.3541(4) 0.0755(17) Uani 1 1 d . . . H47 H 0.7885 0.3070 0.3625 0.091 Uiso 1 1 calc R . . C48 C 0.5967(5) 0.2973(3) 0.2959(3) 0.0574(13) Uani 1 1 d . . . H48 H 0.5990 0.3466 0.2650 0.069 Uiso 1 1 calc R . . N1 N 0.5388(4) 0.3662(2) 0.6099(2) 0.0516(10) Uani 1 1 d . . . N2 N 0.1786(4) 0.1501(2) 0.6002(2) 0.0547(10) Uani 1 1 d . . . N3 N 0.0230(4) 0.3646(2) 0.1068(2) 0.0515(10) Uani 1 1 d . . . N4 N 0.4873(4) 0.1402(2) 0.1056(2) 0.0574(10) Uani 1 1 d . . . Sb1 Sb 0.28559(3) 0.294041(17) 0.691803(17) 0.04063(10) Uani 1 1 d . . . Sb2 Sb 0.31211(3) 0.291971(17) 0.188252(17) 0.04084(10) 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 0.043(2) 0.032(2) 0.044(3) -0.006(2) -0.001(2) -0.0004(19) C2 0.051(3) 0.039(3) 0.049(3) -0.002(2) 0.003(2) -0.006(2) C3 0.071(3) 0.053(3) 0.073(4) -0.009(3) 0.005(3) -0.027(3) C4 0.087(4) 0.073(4) 0.068(4) -0.032(3) -0.004(3) -0.026(3) C5 0.084(4) 0.072(4) 0.045(3) -0.017(3) 0.003(3) -0.021(3) C6 0.061(3) 0.050(3) 0.053(3) -0.008(2) 0.008(2) -0.016(2) C7 0.066(3) 0.043(3) 0.062(3) 0.005(2) 0.007(3) -0.012(2) C8 0.062(4) 0.082(4) 0.089(4) 0.005(3) 0.015(3) 0.008(3) C9 0.105(5) 0.085(4) 0.045(3) 0.002(3) 0.003(3) -0.003(3) C10 0.037(2) 0.031(2) 0.044(3) -0.0005(19) 0.0011(19) -0.0060(18) C11 0.040(2) 0.040(3) 0.046(3) -0.003(2) 0.002(2) -0.005(2) C12 0.053(3) 0.044(3) 0.069(3) -0.017(2) 0.000(3) -0.002(2) C13 0.049(3) 0.040(3) 0.095(4) -0.005(3) -0.001(3) 0.009(2) C14 0.053(3) 0.049(3) 0.080(4) 0.002(3) -0.018(3) 0.002(2) C15 0.052(3) 0.042(3) 0.054(3) -0.005(2) -0.014(2) -0.005(2) C16 0.056(3) 0.057(3) 0.046(3) -0.014(2) -0.003(2) -0.008(2) C17 0.062(4) 0.108(5) 0.106(5) 0.005(4) -0.033(3) 0.009(3) C18 0.065(4) 0.079(4) 0.096(4) 0.003(3) -0.002(3) -0.029(3) C19 0.042(3) 0.050(3) 0.044(3) -0.014(2) 0.002(2) -0.016(2) C20 0.067(3) 0.062(3) 0.049(3) -0.007(3) 0.001(3) -0.023(3) C21 0.109(5) 0.078(4) 0.039(3) 0.003(3) 0.004(3) -0.052(4) C22 0.086(5) 0.134(6) 0.067(4) -0.038(4) 0.034(4) -0.071(5) C23 0.053(4) 0.118(6) 0.096(5) -0.039(4) 0.018(4) -0.027(4) C24 0.041(3) 0.074(4) 0.072(4) -0.020(3) 0.000(3) -0.016(3) C25 0.048(3) 0.034(2) 0.040(3) -0.008(2) -0.003(2) -0.0075(19) C26 0.057(3) 0.033(3) 0.051(3) -0.004(2) -0.002(2) -0.009(2) C27 0.065(3) 0.048(3) 0.077(4) -0.015(3) -0.007(3) 0.009(2) C28 0.081(4) 0.064(4) 0.072(4) -0.030(3) 0.003(3) 0.005(3) C29 0.077(4) 0.070(4) 0.047(3) -0.017(3) -0.003(3) -0.001(3) C30 0.056(3) 0.050(3) 0.050(3) -0.006(2) -0.006(2) 0.001(2) C31 0.067(3) 0.044(3) 0.060(3) 0.007(2) -0.007(3) -0.001(2) C32 0.070(4) 0.093(4) 0.084(4) 0.010(3) -0.023(3) -0.027(3) C33 0.112(5) 0.080(4) 0.054(3) 0.009(3) -0.014(3) -0.018(3) C34 0.038(2) 0.034(2) 0.040(2) -0.0004(19) -0.0023(19) -0.0013(18) C35 0.038(2) 0.044(3) 0.041(3) -0.002(2) -0.005(2) -0.005(2) C36 0.050(3) 0.044(3) 0.057(3) -0.011(2) -0.002(2) -0.008(2) C37 0.045(3) 0.043(3) 0.075(4) 0.000(3) -0.006(3) -0.014(2) C38 0.045(3) 0.044(3) 0.077(4) 0.007(3) 0.016(2) -0.008(2) C39 0.048(3) 0.036(3) 0.054(3) -0.010(2) 0.007(2) -0.001(2) C40 0.052(3) 0.056(3) 0.051(3) -0.012(2) 0.007(2) -0.007(2) C41 0.078(4) 0.107(5) 0.110(5) -0.011(4) 0.039(4) -0.033(4) C42 0.055(3) 0.089(4) 0.087(4) 0.007(3) 0.009(3) 0.005(3) C43 0.037(2) 0.045(3) 0.041(3) -0.007(2) 0.0011(19) -0.004(2) C44 0.045(3) 0.071(4) 0.057(3) 0.002(3) -0.004(2) -0.007(2) C45 0.065(4) 0.086(4) 0.062(4) 0.008(3) -0.004(3) 0.009(3) C46 0.051(3) 0.114(5) 0.055(4) -0.028(4) -0.015(3) 0.017(3) C47 0.045(3) 0.099(5) 0.084(4) -0.036(4) -0.007(3) -0.009(3) C48 0.045(3) 0.057(3) 0.072(3) -0.018(3) 0.002(3) -0.008(2) N1 0.058(2) 0.050(2) 0.046(2) 0.0012(19) 0.0044(19) -0.0012(19) N2 0.044(2) 0.058(3) 0.062(3) -0.003(2) -0.010(2) -0.0046(19) N3 0.063(3) 0.049(2) 0.044(2) 0.0024(19) -0.0086(19) -0.0144(19) N4 0.046(2) 0.067(3) 0.060(3) -0.007(2) 0.014(2) -0.012(2) Sb1 0.04066(18) 0.03761(18) 0.04224(19) -0.00190(14) -0.00107(13) 0.00058(13) Sb2 0.04262(18) 0.03864(18) 0.04247(19) -0.00134(14) 0.00308(13) -0.01000(13) _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 C6 1.392(5) . ? C1 C2 1.397(5) . ? C1 Sb1 2.177(4) . ? C2 C3 1.391(6) . ? C2 C7 1.509(6) . ? C3 C4 1.364(6) . ? C3 H3 0.9300 . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.468(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.452(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.452(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.388(5) . ? C10 C11 1.396(5) . ? C10 Sb1 2.155(4) . ? C11 C12 1.393(6) . ? C11 C16 1.511(5) . ? C12 C13 1.369(6) . ? C12 H12 0.9300 . ? C13 C14 1.356(6) . ? C13 H13 0.9300 . ? C14 C15 1.387(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N2 1.445(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.452(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N2 1.455(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.376(6) . ? C19 C20 1.399(6) . ? C19 Sb1 2.169(4) . ? C20 C21 1.367(6) . ? C20 H20 0.9300 . ? C21 C22 1.379(8) . ? C21 H21 0.9300 . ? C22 C23 1.357(8) . ? C22 H22 0.9300 . ? C23 C24 1.375(7) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.382(5) . ? C25 C26 1.405(5) . ? C25 Sb2 2.184(4) . ? C26 C27 1.381(6) . ? C26 C31 1.506(6) . ? C27 C28 1.370(6) . ? C27 H27 0.9300 . ? C28 C29 1.379(6) . ? C28 H28 0.9300 . ? C29 C30 1.387(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 N3 1.460(5) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 N3 1.452(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 N3 1.463(5) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C39 1.383(5) . ? C34 C35 1.402(5) . ? C34 Sb2 2.158(4) . ? C35 C36 1.379(5) . ? C35 C40 1.510(5) . ? C36 C37 1.377(6) . ? C36 H36 0.9300 . ? C37 C38 1.366(6) . ? C37 H37 0.9300 . ? C38 C39 1.386(5) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 N4 1.450(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 N4 1.449(5) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 N4 1.451(6) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 C44 1.383(6) . ? C43 C48 1.388(5) . ? C43 Sb2 2.157(4) . ? C44 C45 1.378(6) . ? C44 H44 0.9300 . ? C45 C46 1.355(7) . ? C45 H45 0.9300 . ? C46 C47 1.365(7) . ? C46 H46 0.9300 . ? C47 C48 1.387(6) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.7(4) . . ? C6 C1 Sb1 122.3(3) . . ? C2 C1 Sb1 120.0(3) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 C7 120.0(4) . . ? C1 C2 C7 120.3(4) . . ? C4 C3 C2 121.6(5) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 118.9(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 122.2(4) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? N1 C7 C2 111.6(4) . . ? N1 C7 H7A 109.3 . . ? C2 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C2 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.2(4) . . ? C15 C10 Sb1 122.2(3) . . ? C11 C10 Sb1 119.5(3) . . ? C12 C11 C10 119.4(4) . . ? C12 C11 C16 120.0(4) . . ? C10 C11 C16 120.5(4) . . ? C13 C12 C11 120.9(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.3(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.8(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 121.4(4) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? N2 C16 C11 111.3(4) . . ? N2 C16 H16A 109.4 . . ? C11 C16 H16A 109.4 . . ? N2 C16 H16B 109.4 . . ? C11 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 118.3(4) . . ? C24 C19 Sb1 117.0(4) . . ? C20 C19 Sb1 124.6(3) . . ? C21 C20 C19 120.4(5) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.3(6) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.6(5) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 121.0(6) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C19 120.5(5) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C30 C25 C26 117.8(4) . . ? C30 C25 Sb2 122.4(3) . . ? C26 C25 Sb2 119.8(3) . . ? C27 C26 C25 119.6(4) . . ? C27 C26 C31 120.1(4) . . ? C25 C26 C31 120.2(4) . . ? C28 C27 C26 121.9(5) . . ? C28 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? C27 C28 C29 119.2(5) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? C28 C29 C30 119.6(5) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C25 C30 C29 121.9(4) . . ? C25 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? N3 C31 C26 112.3(4) . . ? N3 C31 H31A 109.1 . . ? C26 C31 H31A 109.1 . . ? N3 C31 H31B 109.1 . . ? C26 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? N3 C32 H32A 109.5 . . ? N3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N3 C33 H33A 109.5 . . ? N3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C39 C34 C35 118.1(4) . . ? C39 C34 Sb2 121.9(3) . . ? C35 C34 Sb2 119.7(3) . . ? C36 C35 C34 120.0(4) . . ? C36 C35 C40 120.1(4) . . ? C34 C35 C40 119.9(4) . . ? C37 C36 C35 120.8(4) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C38 C37 C36 120.0(4) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C39 119.9(4) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C34 C39 C38 121.3(4) . . ? C34 C39 H39 119.4 . . ? C38 C39 H39 119.4 . . ? N4 C40 C35 112.0(4) . . ? N4 C40 H40A 109.2 . . ? C35 C40 H40A 109.2 . . ? N4 C40 H40B 109.2 . . ? C35 C40 H40B 109.2 . . ? H40A C40 H40B 107.9 . . ? N4 C41 H41A 109.5 . . ? N4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? N4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N4 C42 H42A 109.5 . . ? N4 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? N4 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C44 C43 C48 117.1(4) . . ? C44 C43 Sb2 125.4(3) . . ? C48 C43 Sb2 117.5(3) . . ? C45 C44 C43 121.2(5) . . ? C45 C44 H44 119.4 . . ? C43 C44 H44 119.4 . . ? C46 C45 C44 120.6(5) . . ? C46 C45 H45 119.7 . . ? C44 C45 H45 119.7 . . ? C45 C46 C47 120.2(5) . . ? C45 C46 H46 119.9 . . ? C47 C46 H46 119.9 . . ? C46 C47 C48 119.5(5) . . ? C46 C47 H47 120.3 . . ? C48 C47 H47 120.3 . . ? C47 C48 C43 121.5(5) . . ? C47 C48 H48 119.3 . . ? C43 C48 H48 119.3 . . ? C9 N1 C8 111.2(4) . . ? C9 N1 C7 111.9(4) . . ? C8 N1 C7 111.2(4) . . ? C16 N2 C17 111.1(4) . . ? C16 N2 C18 111.4(4) . . ? C17 N2 C18 110.9(4) . . ? C32 N3 C31 111.4(4) . . ? C32 N3 C33 111.4(4) . . ? C31 N3 C33 112.2(4) . . ? C41 N4 C40 112.1(4) . . ? C41 N4 C42 110.9(4) . . ? C40 N4 C42 110.9(4) . . ? C10 Sb1 C19 97.64(16) . . ? C10 Sb1 C1 96.09(14) . . ? C19 Sb1 C1 93.76(15) . . ? C43 Sb2 C34 98.48(15) . . ? C43 Sb2 C25 93.23(15) . . ? C34 Sb2 C25 95.99(14) . . ? 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 C6 C1 C2 C3 0.5(6) . . . . ? Sb1 C1 C2 C3 179.1(3) . . . . ? C6 C1 C2 C7 -177.6(4) . . . . ? Sb1 C1 C2 C7 1.0(5) . . . . ? C1 C2 C3 C4 -0.9(7) . . . . ? C7 C2 C3 C4 177.2(5) . . . . ? C2 C3 C4 C5 1.4(8) . . . . ? C3 C4 C5 C6 -1.4(8) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C2 C1 C6 C5 -0.6(7) . . . . ? Sb1 C1 C6 C5 -179.1(3) . . . . ? C3 C2 C7 N1 134.2(4) . . . . ? C1 C2 C7 N1 -47.7(6) . . . . ? C15 C10 C11 C12 -0.3(6) . . . . ? Sb1 C10 C11 C12 175.4(3) . . . . ? C15 C10 C11 C16 179.8(4) . . . . ? Sb1 C10 C11 C16 -4.4(5) . . . . ? C10 C11 C12 C13 -0.5(7) . . . . ? C16 C11 C12 C13 179.4(4) . . . . ? C11 C12 C13 C14 1.0(7) . . . . ? C12 C13 C14 C15 -0.7(8) . . . . ? C13 C14 C15 C10 0.0(7) . . . . ? C11 C10 C15 C14 0.5(6) . . . . ? Sb1 C10 C15 C14 -175.1(3) . . . . ? C12 C11 C16 N2 128.2(4) . . . . ? C10 C11 C16 N2 -51.9(5) . . . . ? C24 C19 C20 C21 -1.3(7) . . . . ? Sb1 C19 C20 C21 -178.2(3) . . . . ? C19 C20 C21 C22 1.1(7) . . . . ? C20 C21 C22 C23 -0.6(8) . . . . ? C21 C22 C23 C24 0.2(9) . . . . ? C22 C23 C24 C19 -0.4(8) . . . . ? C20 C19 C24 C23 0.9(7) . . . . ? Sb1 C19 C24 C23 178.1(4) . . . . ? C30 C25 C26 C27 0.3(6) . . . . ? Sb2 C25 C26 C27 -179.0(3) . . . . ? C30 C25 C26 C31 177.4(4) . . . . ? Sb2 C25 C26 C31 -1.9(5) . . . . ? C25 C26 C27 C28 -0.3(7) . . . . ? C31 C26 C27 C28 -177.4(5) . . . . ? C26 C27 C28 C29 -0.4(8) . . . . ? C27 C28 C29 C30 1.1(8) . . . . ? C26 C25 C30 C29 0.4(6) . . . . ? Sb2 C25 C30 C29 179.6(3) . . . . ? C28 C29 C30 C25 -1.1(7) . . . . ? C27 C26 C31 N3 -133.5(4) . . . . ? C25 C26 C31 N3 49.4(6) . . . . ? C39 C34 C35 C36 1.4(6) . . . . ? Sb2 C34 C35 C36 -173.1(3) . . . . ? C39 C34 C35 C40 -178.8(4) . . . . ? Sb2 C34 C35 C40 6.7(5) . . . . ? C34 C35 C36 C37 -0.9(6) . . . . ? C40 C35 C36 C37 179.3(4) . . . . ? C35 C36 C37 C38 0.4(7) . . . . ? C36 C37 C38 C39 -0.4(7) . . . . ? C35 C34 C39 C38 -1.5(6) . . . . ? Sb2 C34 C39 C38 172.9(3) . . . . ? C37 C38 C39 C34 1.0(7) . . . . ? C36 C35 C40 N4 -129.1(4) . . . . ? C34 C35 C40 N4 51.1(5) . . . . ? C48 C43 C44 C45 0.4(7) . . . . ? Sb2 C43 C44 C45 178.2(3) . . . . ? C43 C44 C45 C46 -0.4(8) . . . . ? C44 C45 C46 C47 0.6(8) . . . . ? C45 C46 C47 C48 -0.7(8) . . . . ? C46 C47 C48 C43 0.7(7) . . . . ? C44 C43 C48 C47 -0.5(6) . . . . ? Sb2 C43 C48 C47 -178.5(3) . . . . ? C2 C7 N1 C9 161.9(4) . . . . ? C2 C7 N1 C8 -73.1(5) . . . . ? C11 C16 N2 C17 168.1(4) . . . . ? C11 C16 N2 C18 -67.8(5) . . . . ? C26 C31 N3 C32 72.5(5) . . . . ? C26 C31 N3 C33 -161.9(4) . . . . ? C35 C40 N4 C41 -166.8(4) . . . . ? C35 C40 N4 C42 68.6(5) . . . . ? C15 C10 Sb1 C19 -82.0(3) . . . . ? C11 C10 Sb1 C19 102.5(3) . . . . ? C15 C10 Sb1 C1 12.7(4) . . . . ? C11 C10 Sb1 C1 -162.9(3) . . . . ? C24 C19 Sb1 C10 -166.5(3) . . . . ? C20 C19 Sb1 C10 10.4(4) . . . . ? C24 C19 Sb1 C1 96.8(3) . . . . ? C20 C19 Sb1 C1 -86.2(4) . . . . ? C6 C1 Sb1 C10 -84.4(4) . . . . ? C2 C1 Sb1 C10 97.1(3) . . . . ? C6 C1 Sb1 C19 13.7(4) . . . . ? C2 C1 Sb1 C19 -164.8(3) . . . . ? C44 C43 Sb2 C34 -4.6(4) . . . . ? C48 C43 Sb2 C34 173.2(3) . . . . ? C44 C43 Sb2 C25 92.0(4) . . . . ? C48 C43 Sb2 C25 -90.2(3) . . . . ? C39 C34 Sb2 C43 83.7(3) . . . . ? C35 C34 Sb2 C43 -102.0(3) . . . . ? C39 C34 Sb2 C25 -10.5(3) . . . . ? C35 C34 Sb2 C25 163.9(3) . . . . ? C30 C25 Sb2 C43 -14.4(4) . . . . ? C26 C25 Sb2 C43 164.9(3) . . . . ? C30 C25 Sb2 C34 84.5(3) . . . . ? C26 C25 Sb2 C34 -96.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.647 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.072 # Attachment 'Compound 2 - CCDC 752088.cif' data_351rich _database_code_depnum_ccdc_archive 'CCDC 752088' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 Br N Sb' _chemical_formula_sum 'C15 H17 Br N Sb' _chemical_formula_weight 412.96 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc ' 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 25.7685(17) _cell_length_b 7.9478(5) _cell_length_c 15.3568(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.2590(10) _cell_angle_gamma 90.00 _cell_volume 3061.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4820 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 4.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.259 _exptl_absorpt_correction_T_max 0.338 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11854 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3115 _reflns_number_gt 2809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0333P)^2^+11.3626P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3115 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.38206(3) 0.22998(8) 0.35457(4) 0.06578(19) Uani 1 1 d . . . C1 C 0.33882(17) 0.6243(5) 0.4205(3) 0.0355(9) Uani 1 1 d . . . C2 C 0.3316(2) 0.7660(7) 0.4680(4) 0.0523(13) Uani 1 1 d . . . C3 C 0.2873(2) 0.8681(8) 0.4378(4) 0.0669(16) Uani 1 1 d . . . H3 H 0.2835 0.9667 0.4684 0.080 Uiso 1 1 calc R . . C4 C 0.2493(2) 0.8245(8) 0.3635(4) 0.0560(14) Uani 1 1 d . . . H4 H 0.2197 0.8930 0.3434 0.067 Uiso 1 1 calc R . . C5 C 0.2552(2) 0.6789(8) 0.3187(4) 0.0581(14) Uani 1 1 d . . . H5 H 0.2289 0.6466 0.2693 0.070 Uiso 1 1 calc R . . C6 C 0.29986(19) 0.5804(7) 0.3469(3) 0.0490(12) Uani 1 1 d . . . H6 H 0.3037 0.4827 0.3156 0.059 Uiso 1 1 calc R . . C7 C 0.3696(2) 0.8015(8) 0.5584(4) 0.0665(16) Uani 1 1 d . . . H7A H 0.3698 0.9211 0.5711 0.080 Uiso 1 1 calc R . . H7B H 0.3574 0.7427 0.6053 0.080 Uiso 1 1 calc R . . C8 C 0.4483(3) 0.8648(8) 0.5064(5) 0.0775(19) Uani 1 1 d . . . H8A H 0.4240 0.8905 0.4506 0.116 Uiso 1 1 calc R . . H8B H 0.4800 0.8147 0.4950 0.116 Uiso 1 1 calc R . . H8C H 0.4574 0.9664 0.5402 0.116 Uiso 1 1 calc R . . C9 C 0.4568(3) 0.7312(9) 0.6476(4) 0.0761(19) Uani 1 1 d . . . H9A H 0.4600 0.8387 0.6768 0.114 Uiso 1 1 calc R . . H9B H 0.4915 0.6924 0.6439 0.114 Uiso 1 1 calc R . . H9C H 0.4412 0.6520 0.6813 0.114 Uiso 1 1 calc R . . C10 C 0.39126(19) 0.3579(6) 0.5730(3) 0.0402(10) Uani 1 1 d . . . C11 C 0.3384(2) 0.3232(6) 0.5726(4) 0.0502(12) Uani 1 1 d . . . H11 H 0.3115 0.3599 0.5251 0.060 Uiso 1 1 calc R . . C12 C 0.3252(3) 0.2351(7) 0.6416(4) 0.0666(16) Uani 1 1 d . . . H12 H 0.2896 0.2146 0.6411 0.080 Uiso 1 1 calc R . . C13 C 0.3644(3) 0.1778(7) 0.7109(4) 0.0711(18) Uani 1 1 d . . . H13 H 0.3554 0.1178 0.7572 0.085 Uiso 1 1 calc R . . C14 C 0.4163(3) 0.2074(8) 0.7126(4) 0.0714(19) Uani 1 1 d . . . H14 H 0.4427 0.1673 0.7599 0.086 Uiso 1 1 calc R . . C15 C 0.4304(2) 0.2984(7) 0.6435(3) 0.0570(14) Uani 1 1 d . . . H15 H 0.4661 0.3189 0.6450 0.068 Uiso 1 1 calc R . . N1 N 0.42294(15) 0.7469(5) 0.5574(3) 0.0410(9) Uani 1 1 d . . . Sb1 Sb 0.413037(11) 0.49262(4) 0.465604(19) 0.03682(11) 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 Br1 0.0721(4) 0.0565(3) 0.0620(4) -0.0229(3) 0.0015(3) 0.0055(3) C1 0.033(2) 0.038(2) 0.034(2) 0.0065(18) 0.0055(18) 0.0044(18) C2 0.043(3) 0.051(3) 0.057(3) -0.006(2) -0.001(2) 0.012(2) C3 0.055(3) 0.060(4) 0.083(4) -0.006(3) 0.010(3) 0.020(3) C4 0.041(3) 0.065(4) 0.060(3) 0.023(3) 0.009(2) 0.015(3) C5 0.040(3) 0.074(4) 0.051(3) 0.014(3) -0.008(2) 0.000(3) C6 0.044(3) 0.052(3) 0.046(3) -0.001(2) 0.001(2) -0.002(2) C7 0.060(3) 0.065(4) 0.075(4) -0.019(3) 0.016(3) 0.008(3) C8 0.084(5) 0.057(4) 0.096(5) 0.001(3) 0.031(4) -0.016(3) C9 0.076(4) 0.078(4) 0.063(4) -0.022(3) -0.008(3) 0.005(3) C10 0.050(3) 0.032(2) 0.038(2) -0.0018(18) 0.008(2) 0.006(2) C11 0.056(3) 0.041(3) 0.055(3) 0.005(2) 0.015(2) 0.004(2) C12 0.084(4) 0.054(3) 0.073(4) 0.006(3) 0.041(4) -0.002(3) C13 0.121(6) 0.045(3) 0.056(4) 0.005(3) 0.037(4) 0.002(4) C14 0.111(6) 0.057(4) 0.038(3) 0.008(2) 0.000(3) 0.013(4) C15 0.064(3) 0.055(3) 0.045(3) 0.002(2) -0.001(2) 0.009(3) N1 0.036(2) 0.040(2) 0.043(2) -0.0044(17) 0.0025(16) -0.0023(17) Sb1 0.03159(17) 0.04054(18) 0.03750(18) -0.00282(12) 0.00622(12) 0.00298(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 Br1 Sb1 2.6977(6) . ? C1 C6 1.374(6) . ? C1 C2 1.378(7) . ? C1 Sb1 2.150(4) . ? C2 C3 1.390(7) . ? C2 C7 1.531(8) . ? C3 C4 1.367(8) . ? C3 H3 0.9300 . ? C4 C5 1.372(8) . ? C4 H4 0.9300 . ? C5 C6 1.377(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.444(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.467(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.464(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.383(7) . ? C10 C11 1.390(7) . ? C10 Sb1 2.146(5) . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 C13 1.367(9) . ? C12 H12 0.9300 . ? C13 C14 1.352(9) . ? C13 H13 0.9300 . ? C14 C15 1.399(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 Sb1 2.444(4) . ? 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 C6 C1 C2 118.7(4) . . ? C6 C1 Sb1 124.7(4) . . ? C2 C1 Sb1 116.5(3) . . ? C1 C2 C3 120.1(5) . . ? C1 C2 C7 119.6(4) . . ? C3 C2 C7 120.1(5) . . ? C4 C3 C2 120.4(6) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.5(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 121.0(5) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N1 C7 C2 110.3(4) . . ? N1 C7 H7A 109.6 . . ? C2 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.3(5) . . ? C15 C10 Sb1 120.0(4) . . ? C11 C10 Sb1 121.7(3) . . ? C12 C11 C10 120.8(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.1(6) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.1(6) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C7 N1 C9 112.2(5) . . ? C7 N1 C8 110.8(5) . . ? C9 N1 C8 108.5(5) . . ? C7 N1 Sb1 106.3(3) . . ? C9 N1 Sb1 115.8(3) . . ? C8 N1 Sb1 102.8(3) . . ? C10 Sb1 C1 96.90(17) . . ? C10 Sb1 N1 88.88(15) . . ? C1 Sb1 N1 75.57(15) . . ? C10 Sb1 Br1 90.46(12) . . ? C1 Sb1 Br1 93.47(12) . . ? N1 Sb1 Br1 168.85(9) . . ? 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 C6 C1 C2 C3 -4.4(8) . . . . ? Sb1 C1 C2 C3 173.3(5) . . . . ? C6 C1 C2 C7 170.0(5) . . . . ? Sb1 C1 C2 C7 -12.4(7) . . . . ? C1 C2 C3 C4 3.3(9) . . . . ? C7 C2 C3 C4 -171.1(6) . . . . ? C2 C3 C4 C5 0.0(9) . . . . ? C3 C4 C5 C6 -2.1(9) . . . . ? C2 C1 C6 C5 2.4(8) . . . . ? Sb1 C1 C6 C5 -175.1(4) . . . . ? C4 C5 C6 C1 0.9(8) . . . . ? C1 C2 C7 N1 35.0(7) . . . . ? C3 C2 C7 N1 -150.7(6) . . . . ? C15 C10 C11 C12 1.4(7) . . . . ? Sb1 C10 C11 C12 179.3(4) . . . . ? C10 C11 C12 C13 -1.3(9) . . . . ? C11 C12 C13 C14 0.3(9) . . . . ? C12 C13 C14 C15 0.4(9) . . . . ? C11 C10 C15 C14 -0.7(8) . . . . ? Sb1 C10 C15 C14 -178.6(4) . . . . ? C13 C14 C15 C10 -0.2(9) . . . . ? C2 C7 N1 C9 -163.0(5) . . . . ? C2 C7 N1 C8 75.5(6) . . . . ? C2 C7 N1 Sb1 -35.4(5) . . . . ? C15 C10 Sb1 C1 -157.3(4) . . . . ? C11 C10 Sb1 C1 24.8(4) . . . . ? C15 C10 Sb1 N1 -82.0(4) . . . . ? C11 C10 Sb1 N1 100.1(4) . . . . ? C15 C10 Sb1 Br1 109.1(4) . . . . ? C11 C10 Sb1 Br1 -68.7(4) . . . . ? C6 C1 Sb1 C10 -101.8(4) . . . . ? C2 C1 Sb1 C10 80.7(4) . . . . ? C6 C1 Sb1 N1 171.2(4) . . . . ? C2 C1 Sb1 N1 -6.3(4) . . . . ? C6 C1 Sb1 Br1 -10.9(4) . . . . ? C2 C1 Sb1 Br1 171.6(4) . . . . ? C7 N1 Sb1 C10 -73.6(4) . . . . ? C9 N1 Sb1 C10 51.7(4) . . . . ? C8 N1 Sb1 C10 169.9(4) . . . . ? C7 N1 Sb1 C1 23.8(4) . . . . ? C9 N1 Sb1 C1 149.2(4) . . . . ? C8 N1 Sb1 C1 -92.7(4) . . . . ? C7 N1 Sb1 Br1 13.1(7) . . . . ? C9 N1 Sb1 Br1 138.5(5) . . . . ? C8 N1 Sb1 Br1 -103.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.739 _refine_diff_density_min -0.905 _refine_diff_density_rms 0.101 # Attachment 'Compound 3 - CCDC - 752089.cif' data_364rich _database_code_depnum_ccdc_archive 'CCDC 752089' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 I N Sb' _chemical_formula_sum 'C15 H17 I N Sb' _chemical_formula_weight 459.95 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2997(9) _cell_length_b 12.2869(8) _cell_length_c 10.4529(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.1290(10) _cell_angle_gamma 90.00 _cell_volume 1593.29(18) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5153 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.66 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.917 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 3.653 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.370 _exptl_absorpt_correction_T_max 0.521 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12446 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3248 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0168P)^2^+1.2670P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3248 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3347(3) -0.0765(3) 0.8782(4) 0.0420(8) Uani 1 1 d . . . C2 C 0.2927(3) -0.1318(3) 0.7533(4) 0.0458(9) Uani 1 1 d . . . C3 C 0.3153(3) -0.2412(3) 0.7466(4) 0.0535(11) Uani 1 1 d . . . H3 H 0.2870 -0.2780 0.6635 0.064 Uiso 1 1 calc R . . C4 C 0.3795(4) -0.2961(3) 0.8625(5) 0.0578(11) Uani 1 1 d . . . H4 H 0.3937 -0.3697 0.8575 0.069 Uiso 1 1 calc R . . C5 C 0.4222(3) -0.2419(3) 0.9851(5) 0.0547(11) Uani 1 1 d . . . H5 H 0.4664 -0.2786 1.0628 0.066 Uiso 1 1 calc R . . C6 C 0.3998(3) -0.1323(3) 0.9934(4) 0.0470(9) Uani 1 1 d . . . H6 H 0.4286 -0.0961 1.0769 0.056 Uiso 1 1 calc R . . C7 C 0.2224(4) -0.0710(3) 0.6272(4) 0.0550(11) Uani 1 1 d . . . H7A H 0.2280 -0.1044 0.5460 0.066 Uiso 1 1 calc R . . H7B H 0.1477 -0.0752 0.6202 0.066 Uiso 1 1 calc R . . C8 C 0.3583(4) 0.0553(4) 0.6087(5) 0.0697(13) Uani 1 1 d . . . H8A H 0.4124 0.0091 0.6705 0.104 Uiso 1 1 calc R . . H8B H 0.3821 0.1296 0.6229 0.104 Uiso 1 1 calc R . . H8C H 0.3465 0.0346 0.5158 0.104 Uiso 1 1 calc R . . C9 C 0.1718(4) 0.1111(4) 0.5348(5) 0.0751(15) Uani 1 1 d . . . H9A H 0.1656 0.0912 0.4434 0.113 Uiso 1 1 calc R . . H9B H 0.1911 0.1866 0.5501 0.113 Uiso 1 1 calc R . . H9C H 0.1040 0.0992 0.5458 0.113 Uiso 1 1 calc R . . C10 C 0.1295(3) 0.0796(3) 0.8350(4) 0.0450(9) Uani 1 1 d . . . C11 C 0.0824(3) -0.0150(3) 0.8588(4) 0.0499(10) Uani 1 1 d . . . H11 H 0.1242 -0.0769 0.8905 0.060 Uiso 1 1 calc R . . C12 C -0.0267(3) -0.0175(4) 0.8353(4) 0.0612(12) Uani 1 1 d . . . H12 H -0.0578 -0.0814 0.8512 0.073 Uiso 1 1 calc R . . C13 C -0.0893(4) 0.0724(4) 0.7893(5) 0.0680(13) Uani 1 1 d . . . H13 H -0.1626 0.0698 0.7745 0.082 Uiso 1 1 calc R . . C14 C -0.0442(4) 0.1662(5) 0.7650(5) 0.0750(15) Uani 1 1 d . . . H14 H -0.0869 0.2274 0.7326 0.090 Uiso 1 1 calc R . . C15 C 0.0654(4) 0.1704(4) 0.7885(5) 0.0624(12) Uani 1 1 d . . . H15 H 0.0959 0.2348 0.7729 0.075 Uiso 1 1 calc R . . I1 I 0.33963(2) 0.10311(2) 1.17302(3) 0.05619(10) Uani 1 1 d . . . N1 N 0.2558(3) 0.0439(3) 0.6348(3) 0.0508(8) Uani 1 1 d . . . Sb1 Sb 0.29915(2) 0.094661(19) 0.87294(3) 0.04218(9) 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 0.039(2) 0.043(2) 0.045(2) -0.0012(17) 0.0161(17) 0.0006(16) C2 0.046(2) 0.046(2) 0.050(2) -0.0040(18) 0.0228(18) -0.0055(18) C3 0.060(3) 0.051(2) 0.057(3) -0.010(2) 0.031(2) -0.010(2) C4 0.062(3) 0.042(2) 0.078(3) 0.000(2) 0.036(2) 0.002(2) C5 0.049(2) 0.053(2) 0.065(3) 0.013(2) 0.024(2) 0.0052(19) C6 0.043(2) 0.051(2) 0.049(2) 0.0065(18) 0.0190(18) 0.0046(18) C7 0.062(3) 0.058(3) 0.041(2) -0.0075(19) 0.014(2) -0.008(2) C8 0.087(4) 0.070(3) 0.064(3) 0.008(2) 0.042(3) -0.005(3) C9 0.092(4) 0.072(3) 0.043(3) 0.007(2) 0.002(2) 0.008(3) C10 0.042(2) 0.047(2) 0.038(2) -0.0061(17) 0.0049(16) 0.0013(17) C11 0.047(2) 0.048(2) 0.049(2) -0.0045(18) 0.0108(19) 0.0040(19) C12 0.054(3) 0.066(3) 0.064(3) -0.015(2) 0.022(2) -0.014(2) C13 0.042(2) 0.088(4) 0.067(3) -0.018(3) 0.011(2) 0.003(3) C14 0.057(3) 0.079(4) 0.074(3) -0.003(3) 0.005(2) 0.024(3) C15 0.056(3) 0.052(3) 0.066(3) -0.002(2) 0.006(2) 0.008(2) I1 0.0650(2) 0.05498(18) 0.04139(16) -0.00476(12) 0.01053(13) -0.00134(13) N1 0.057(2) 0.053(2) 0.0384(18) 0.0009(15) 0.0127(16) -0.0024(17) Sb1 0.04249(15) 0.03879(15) 0.03985(15) 0.00041(11) 0.00831(11) -0.00418(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.384(5) . ? C1 C2 1.397(5) . ? C1 Sb1 2.152(4) . ? C2 C3 1.385(5) . ? C2 C7 1.510(6) . ? C3 C4 1.380(6) . ? C3 H3 0.9300 . ? C4 C5 1.372(6) . ? C4 H4 0.9300 . ? C5 C6 1.388(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.474(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.490(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.477(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.382(5) . ? C10 C11 1.384(5) . ? C10 Sb1 2.154(4) . ? C11 C12 1.383(5) . ? C11 H11 0.9300 . ? C12 C13 1.361(6) . ? C12 H12 0.9300 . ? C13 C14 1.365(7) . ? C13 H13 0.9300 . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? I1 Sb1 2.9870(4) . ? N1 Sb1 2.426(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 C6 C1 C2 119.1(4) . . ? C6 C1 Sb1 124.7(3) . . ? C2 C1 Sb1 116.2(3) . . ? C3 C2 C1 119.9(4) . . ? C3 C2 C7 120.9(4) . . ? C1 C2 C7 119.2(4) . . ? C4 C3 C2 120.4(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.2(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.4(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 C2 110.3(3) . . ? N1 C7 H7A 109.6 . . ? C2 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.7(4) . . ? C15 C10 Sb1 117.9(3) . . ? C11 C10 Sb1 123.4(3) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.9(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.8(4) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.2(5) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.4(5) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C7 N1 C9 111.2(3) . . ? C7 N1 C8 111.0(3) . . ? C9 N1 C8 109.1(4) . . ? C7 N1 Sb1 104.9(2) . . ? C9 N1 Sb1 115.0(3) . . ? C8 N1 Sb1 105.6(3) . . ? C1 Sb1 C10 97.28(14) . . ? C1 Sb1 N1 75.15(13) . . ? C10 Sb1 N1 86.75(13) . . ? C1 Sb1 I1 93.00(10) . . ? C10 Sb1 I1 88.67(10) . . ? N1 Sb1 I1 166.62(8) . . ? 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 C6 C1 C2 C3 0.9(6) . . . . ? Sb1 C1 C2 C3 177.5(3) . . . . ? C6 C1 C2 C7 -179.6(4) . . . . ? Sb1 C1 C2 C7 -2.9(5) . . . . ? C1 C2 C3 C4 -0.3(6) . . . . ? C7 C2 C3 C4 -179.8(4) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 C6 1.0(6) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? Sb1 C1 C6 C5 -176.9(3) . . . . ? C4 C5 C6 C1 -0.4(6) . . . . ? C3 C2 C7 N1 -148.8(4) . . . . ? C1 C2 C7 N1 31.7(5) . . . . ? C15 C10 C11 C12 0.3(6) . . . . ? Sb1 C10 C11 C12 178.2(3) . . . . ? C10 C11 C12 C13 -0.2(6) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? C12 C13 C14 C15 -0.7(7) . . . . ? C11 C10 C15 C14 -0.6(6) . . . . ? Sb1 C10 C15 C14 -178.6(4) . . . . ? C13 C14 C15 C10 0.8(7) . . . . ? C2 C7 N1 C9 -164.2(4) . . . . ? C2 C7 N1 C8 74.2(4) . . . . ? C2 C7 N1 Sb1 -39.4(4) . . . . ? C6 C1 Sb1 C10 -113.9(3) . . . . ? C2 C1 Sb1 C10 69.7(3) . . . . ? C6 C1 Sb1 N1 161.5(3) . . . . ? C2 C1 Sb1 N1 -15.0(3) . . . . ? C6 C1 Sb1 I1 -24.8(3) . . . . ? C2 C1 Sb1 I1 158.7(3) . . . . ? C15 C10 Sb1 C1 -163.6(3) . . . . ? C11 C10 Sb1 C1 18.5(3) . . . . ? C15 C10 Sb1 N1 -89.0(3) . . . . ? C11 C10 Sb1 N1 93.0(3) . . . . ? C15 C10 Sb1 I1 103.5(3) . . . . ? C11 C10 Sb1 I1 -74.4(3) . . . . ? C7 N1 Sb1 C1 29.9(3) . . . . ? C9 N1 Sb1 C1 152.3(3) . . . . ? C8 N1 Sb1 C1 -87.4(3) . . . . ? C7 N1 Sb1 C10 -68.5(3) . . . . ? C9 N1 Sb1 C10 53.9(3) . . . . ? C8 N1 Sb1 C10 174.1(3) . . . . ? C7 N1 Sb1 I1 1.6(5) . . . . ? C9 N1 Sb1 I1 124.0(4) . . . . ? C8 N1 Sb1 I1 -115.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.442 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.078 # Attachment 'Compound 8 - CCDC - 752090.cif' data_365rich _database_code_depnum_ccdc_archive 'CCDC 752090' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 I N Sb' _chemical_formula_sum 'C18 H23 I N Sb' _chemical_formula_weight 502.02 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8671(6) _cell_length_b 15.2192(9) _cell_length_c 13.3666(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.1590(10) _cell_angle_gamma 90.00 _cell_volume 1946.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5043 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 2.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.491 _exptl_absorpt_correction_T_max 0.625 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15379 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3976 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0264P)^2^+4.0211P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3976 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.89579(3) 0.084192(19) 0.37926(2) 0.03468(10) Uani 1 1 d . . . I1 I 1.17293(4) 0.10754(2) 0.33637(4) 0.06063(13) Uani 1 1 d . . . C10 C 0.8182(5) 0.0144(3) 0.2354(3) 0.0362(10) Uani 1 1 d . . . C2 C 0.6889(5) 0.2358(3) 0.3183(3) 0.0387(10) Uani 1 1 d . . . C1 C 0.8325(5) 0.2180(3) 0.3407(3) 0.0361(10) Uani 1 1 d . . . C5 C 0.8749(6) 0.3723(3) 0.3230(5) 0.0535(13) Uani 1 1 d . . . H5 H 0.9377 0.4182 0.3247 0.064 Uiso 1 1 calc R . . C6 C 0.9240(5) 0.2876(3) 0.3450(4) 0.0464(12) Uani 1 1 d . . . H6 H 1.0198 0.2772 0.3628 0.056 Uiso 1 1 calc R . . C11 C 0.7828(6) 0.0510(4) 0.1362(4) 0.0501(12) Uani 1 1 d . . . C3 C 0.6420(5) 0.3204(3) 0.2974(4) 0.0505(13) Uani 1 1 d . . . H3 H 0.5465 0.3317 0.2820 0.061 Uiso 1 1 calc R . . C15 C 0.7991(5) -0.0761(3) 0.2452(4) 0.0398(10) Uani 1 1 d . . . C13 C 0.6972(7) -0.0900(4) 0.0629(5) 0.0672(17) Uani 1 1 d . . . C4 C 0.7344(6) 0.3888(3) 0.2987(5) 0.0579(15) Uani 1 1 d . . . H4 H 0.7014 0.4457 0.2833 0.070 Uiso 1 1 calc R . . C16 C 0.8132(8) 0.1454(4) 0.1148(4) 0.0695(18) Uani 1 1 d . . . H16A H 0.8039 0.1531 0.0421 0.104 Uiso 1 1 calc R . . H16B H 0.9068 0.1600 0.1516 0.104 Uiso 1 1 calc R . . H16C H 0.7484 0.1832 0.1370 0.104 Uiso 1 1 calc R . . C12 C 0.7220(7) -0.0019(4) 0.0528(4) 0.0701(18) Uani 1 1 d . . . H12 H 0.6969 0.0232 -0.0126 0.084 Uiso 1 1 calc R . . C18 C 0.8489(7) -0.1258(4) 0.3456(4) 0.0605(15) Uani 1 1 d . . . H18A H 0.8231 -0.1865 0.3349 0.091 Uiso 1 1 calc R . . H18B H 0.8064 -0.1013 0.3967 0.091 Uiso 1 1 calc R . . H18C H 0.9487 -0.1211 0.3687 0.091 Uiso 1 1 calc R . . N1 N 0.6524(4) 0.0939(2) 0.3927(3) 0.0388(9) Uani 1 1 d . . . C7 C 0.5906(5) 0.1598(3) 0.3144(4) 0.0477(12) Uani 1 1 d . . . H7A H 0.5032 0.1807 0.3267 0.057 Uiso 1 1 calc R . . H7B H 0.5707 0.1332 0.2465 0.057 Uiso 1 1 calc R . . C9 C 0.5713(5) 0.0115(3) 0.3752(5) 0.0556(14) Uani 1 1 d . . . H9A H 0.6102 -0.0296 0.4290 0.083 Uiso 1 1 calc R . . H9B H 0.5749 -0.0129 0.3097 0.083 Uiso 1 1 calc R . . H9C H 0.4759 0.0235 0.3755 0.083 Uiso 1 1 calc R . . C14 C 0.7374(5) -0.1261(4) 0.1590(4) 0.0498(12) Uani 1 1 d . . . H14 H 0.7232 -0.1858 0.1671 0.060 Uiso 1 1 calc R . . C8 C 0.6582(6) 0.1268(4) 0.4965(4) 0.0553(14) Uani 1 1 d . . . H8A H 0.7126 0.1798 0.5083 0.083 Uiso 1 1 calc R . . H8B H 0.7006 0.0833 0.5465 0.083 Uiso 1 1 calc R . . H8C H 0.5652 0.1388 0.5029 0.083 Uiso 1 1 calc R . . C17 C 0.6308(10) -0.1452(6) -0.0312(6) 0.117(3) Uani 1 1 d . . . H17A H 0.6755 -0.1327 -0.0858 0.175 Uiso 1 1 calc R . . H17B H 0.5331 -0.1315 -0.0535 0.175 Uiso 1 1 calc R . . H17C H 0.6419 -0.2064 -0.0136 0.175 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 Sb1 0.03225(17) 0.03157(17) 0.03833(17) 0.00128(12) 0.00498(12) 0.00037(12) I1 0.0379(2) 0.0460(2) 0.1029(3) -0.00445(19) 0.02659(19) 0.00311(14) C10 0.036(2) 0.038(2) 0.034(2) -0.0038(19) 0.0081(19) -0.0001(19) C2 0.032(2) 0.044(3) 0.042(2) 0.005(2) 0.0122(19) 0.0041(19) C1 0.035(2) 0.034(2) 0.041(2) 0.0014(19) 0.0139(19) 0.0018(18) C5 0.058(3) 0.034(3) 0.078(4) 0.006(3) 0.035(3) -0.002(2) C6 0.038(3) 0.039(3) 0.066(3) 0.000(2) 0.021(2) 0.002(2) C11 0.062(3) 0.050(3) 0.039(3) 0.003(2) 0.013(2) 0.009(3) C3 0.039(3) 0.054(3) 0.063(3) 0.017(3) 0.021(2) 0.014(2) C15 0.033(2) 0.041(3) 0.046(3) -0.002(2) 0.011(2) 0.0005(19) C13 0.071(4) 0.061(4) 0.059(4) -0.017(3) -0.006(3) 0.007(3) C4 0.067(4) 0.038(3) 0.076(4) 0.015(3) 0.032(3) 0.013(3) C16 0.110(5) 0.056(4) 0.044(3) 0.014(3) 0.022(3) 0.005(3) C12 0.094(5) 0.079(4) 0.031(3) 0.003(3) 0.002(3) 0.019(4) C18 0.086(4) 0.040(3) 0.056(3) 0.003(3) 0.016(3) 0.000(3) N1 0.035(2) 0.038(2) 0.047(2) -0.0008(17) 0.0165(17) -0.0055(16) C7 0.028(2) 0.055(3) 0.059(3) 0.010(2) 0.008(2) 0.002(2) C9 0.042(3) 0.048(3) 0.081(4) -0.003(3) 0.023(3) -0.015(2) C14 0.046(3) 0.043(3) 0.060(3) -0.008(2) 0.012(2) 0.002(2) C8 0.067(4) 0.051(3) 0.058(3) 0.002(3) 0.034(3) -0.004(3) C17 0.146(8) 0.095(6) 0.080(5) -0.031(5) -0.027(5) 0.000(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 Sb1 C1 2.156(4) . ? Sb1 C10 2.166(4) . ? Sb1 N1 2.456(4) . ? Sb1 I1 2.9496(5) . ? C10 C15 1.400(6) . ? C10 C11 1.401(6) . ? C2 C3 1.374(7) . ? C2 C1 1.401(6) . ? C2 C7 1.501(7) . ? C1 C6 1.383(6) . ? C5 C4 1.367(8) . ? C5 C6 1.384(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C11 C12 1.387(8) . ? C11 C16 1.509(8) . ? C3 C4 1.382(7) . ? C3 H3 0.9300 . ? C15 C14 1.391(7) . ? C15 C18 1.514(7) . ? C13 C14 1.364(8) . ? C13 C12 1.374(9) . ? C13 C17 1.522(8) . ? C4 H4 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 H12 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 C8 1.463(6) . ? N1 C7 1.470(6) . ? N1 C9 1.475(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C14 H14 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 C1 Sb1 C10 103.44(17) . . ? C1 Sb1 N1 74.31(14) . . ? C10 Sb1 N1 87.42(15) . . ? C1 Sb1 I1 93.88(12) . . ? C10 Sb1 I1 91.70(12) . . ? N1 Sb1 I1 167.57(9) . . ? C15 C10 C11 118.1(4) . . ? C15 C10 Sb1 115.2(3) . . ? C11 C10 Sb1 126.7(3) . . ? C3 C2 C1 119.8(4) . . ? C3 C2 C7 122.1(4) . . ? C1 C2 C7 118.0(4) . . ? C6 C1 C2 118.5(4) . . ? C6 C1 Sb1 124.4(3) . . ? C2 C1 Sb1 116.8(3) . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.9(5) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C12 C11 C10 119.2(5) . . ? C12 C11 C16 117.9(5) . . ? C10 C11 C16 122.9(5) . . ? C2 C3 C4 121.0(5) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C14 C15 C10 120.2(4) . . ? C14 C15 C18 116.2(4) . . ? C10 C15 C18 123.5(4) . . ? C14 C13 C12 117.9(5) . . ? C14 C13 C17 121.5(6) . . ? C12 C13 C17 120.6(6) . . ? C5 C4 C3 119.5(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C12 C11 122.7(5) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 N1 C7 110.8(4) . . ? C8 N1 C9 109.5(4) . . ? C7 N1 C9 110.7(4) . . ? C8 N1 Sb1 106.2(3) . . ? C7 N1 Sb1 103.4(3) . . ? C9 N1 Sb1 116.1(3) . . ? N1 C7 C2 110.4(4) . . ? N1 C7 H7A 109.6 . . ? C2 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C13 C14 C15 121.8(5) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C1 Sb1 C10 C15 -157.8(3) . . . . ? N1 Sb1 C10 C15 -84.6(3) . . . . ? I1 Sb1 C10 C15 107.8(3) . . . . ? C1 Sb1 C10 C11 20.4(4) . . . . ? N1 Sb1 C10 C11 93.6(4) . . . . ? I1 Sb1 C10 C11 -74.0(4) . . . . ? C3 C2 C1 C6 2.5(7) . . . . ? C7 C2 C1 C6 -179.7(4) . . . . ? C3 C2 C1 Sb1 177.3(4) . . . . ? C7 C2 C1 Sb1 -4.9(6) . . . . ? C10 Sb1 C1 C6 -117.1(4) . . . . ? N1 Sb1 C1 C6 159.5(4) . . . . ? I1 Sb1 C1 C6 -24.4(4) . . . . ? C10 Sb1 C1 C2 68.4(4) . . . . ? N1 Sb1 C1 C2 -15.0(3) . . . . ? I1 Sb1 C1 C2 161.1(3) . . . . ? C2 C1 C6 C5 -2.9(7) . . . . ? Sb1 C1 C6 C5 -177.3(4) . . . . ? C4 C5 C6 C1 1.4(8) . . . . ? C15 C10 C11 C12 4.3(7) . . . . ? Sb1 C10 C11 C12 -173.9(4) . . . . ? C15 C10 C11 C16 -173.2(5) . . . . ? Sb1 C10 C11 C16 8.7(8) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C7 C2 C3 C4 -178.2(5) . . . . ? C11 C10 C15 C14 -4.5(7) . . . . ? Sb1 C10 C15 C14 173.9(3) . . . . ? C11 C10 C15 C18 172.4(5) . . . . ? Sb1 C10 C15 C18 -9.2(6) . . . . ? C6 C5 C4 C3 0.6(9) . . . . ? C2 C3 C4 C5 -1.0(9) . . . . ? C14 C13 C12 C11 -1.4(10) . . . . ? C17 C13 C12 C11 -179.7(7) . . . . ? C10 C11 C12 C13 -1.4(9) . . . . ? C16 C11 C12 C13 176.2(6) . . . . ? C1 Sb1 N1 C8 -85.1(3) . . . . ? C10 Sb1 N1 C8 170.2(3) . . . . ? I1 Sb1 N1 C8 -103.6(5) . . . . ? C1 Sb1 N1 C7 31.6(3) . . . . ? C10 Sb1 N1 C7 -73.2(3) . . . . ? I1 Sb1 N1 C7 13.0(6) . . . . ? C1 Sb1 N1 C9 152.9(4) . . . . ? C10 Sb1 N1 C9 48.2(4) . . . . ? I1 Sb1 N1 C9 134.4(4) . . . . ? C8 N1 C7 C2 70.4(5) . . . . ? C9 N1 C7 C2 -168.0(4) . . . . ? Sb1 N1 C7 C2 -43.0(4) . . . . ? C3 C2 C7 N1 -146.3(5) . . . . ? C1 C2 C7 N1 36.0(6) . . . . ? C12 C13 C14 C15 1.3(9) . . . . ? C17 C13 C14 C15 179.5(6) . . . . ? C10 C15 C14 C13 1.7(8) . . . . ? C18 C15 C14 C13 -175.4(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.707 _refine_diff_density_min -1.168 _refine_diff_density_rms 0.095 # Attachment 'Compound 6 - CCDC - 752091.cif' data_410r _database_code_depnum_ccdc_archive 'CCDC 752091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N Sb' _chemical_formula_sum 'C24 H28 N Sb' _chemical_formula_weight 452.22 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4829(17) _cell_length_b 37.717(8) _cell_length_c 6.7885(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.986(3) _cell_angle_gamma 90.00 _cell_volume 2145.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6607 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 26.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.714 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15307 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3758 _reflns_number_gt 3413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0307P)^2^+12.0887P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3758 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.376 _refine_ls_restrained_S_all 1.376 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7277(9) 0.1631(2) 0.6158(13) 0.0350(19) Uani 1 1 d . . . C2 C 0.6315(11) 0.1455(2) 0.7349(15) 0.050(2) Uani 1 1 d . . . C3 C 0.5449(12) 0.1649(3) 0.8535(16) 0.062(3) Uani 1 1 d . . . H3 H 0.4793 0.1531 0.9301 0.074 Uiso 1 1 calc R . . C4 C 0.5542(12) 0.2010(3) 0.8597(15) 0.055(3) Uani 1 1 d . . . H4 H 0.4960 0.2136 0.9415 0.066 Uiso 1 1 calc R . . C5 C 0.6479(12) 0.2186(3) 0.7473(15) 0.053(3) Uani 1 1 d . . . H5 H 0.6535 0.2432 0.7506 0.064 Uiso 1 1 calc R . . C6 C 0.7346(11) 0.1994(2) 0.6282(13) 0.043(2) Uani 1 1 d . . . H6 H 0.8003 0.2115 0.5534 0.052 Uiso 1 1 calc R . . C7 C 0.6309(15) 0.1053(3) 0.7518(19) 0.073(3) Uani 1 1 d . . . H7A H 0.7257 0.0979 0.8411 0.087 Uiso 1 1 calc R . . H7B H 0.5388 0.0981 0.8106 0.087 Uiso 1 1 calc R . . C8 C 0.4765(6) 0.0950(3) 0.4339(13) 0.100(5) Uani 1 1 d . . . H8A H 0.3885 0.0878 0.4981 0.149 Uiso 1 1 calc R . . H8B H 0.4736 0.0821 0.3115 0.149 Uiso 1 1 calc R . . H8C H 0.4688 0.1200 0.4057 0.149 Uiso 1 1 calc R . . C10 C 1.0101(6) 0.10137(14) 0.5831(7) 0.0309(18) Uani 1 1 d R . . C11 C 1.0867(6) 0.10940(13) 0.7750(8) 0.037(2) Uani 1 1 d R . . C12 C 1.1821(5) 0.08341(13) 0.8833(7) 0.048(2) Uani 1 1 d R . . H12 H 1.2327 0.0891 1.0109 0.058 Uiso 1 1 calc R . . C13 C 1.2048(11) 0.0505(3) 0.8128(17) 0.053(3) Uani 1 1 d . . . C14 C 1.1330(11) 0.0434(2) 0.6223(17) 0.052(3) Uani 1 1 d . . . H14 H 1.1490 0.0213 0.5685 0.062 Uiso 1 1 calc R . . C15 C 1.0376(10) 0.0676(2) 0.5060(13) 0.038(2) Uani 1 1 d . . . C16 C 1.0705(11) 0.1445(2) 0.8744(13) 0.048(2) Uani 1 1 d . . . H16A H 1.0612 0.1630 0.7763 0.072 Uiso 1 1 calc R . . H16B H 1.1629 0.1486 0.9727 0.072 Uiso 1 1 calc R . . H16C H 0.9769 0.1443 0.9378 0.072 Uiso 1 1 calc R . . C17 C 1.3061(15) 0.0230(4) 0.939(2) 0.090(4) Uani 1 1 d . . . H17A H 1.4042 0.0337 1.0009 0.135 Uiso 1 1 calc R . . H17B H 1.3291 0.0037 0.8559 0.135 Uiso 1 1 calc R . . H17C H 1.2488 0.0143 1.0405 0.135 Uiso 1 1 calc R . . C18 C 0.9668(14) 0.0571(3) 0.2942(15) 0.060(3) Uani 1 1 d . . . H18A H 1.0043 0.0730 0.2016 0.090 Uiso 1 1 calc R . . H18B H 0.8525 0.0582 0.2790 0.090 Uiso 1 1 calc R . . H18C H 0.9990 0.0333 0.2686 0.090 Uiso 1 1 calc R . . C19 C 1.0147(10) 0.1758(2) 0.3521(12) 0.0343(19) Uani 1 1 d . . . C20 C 1.1768(11) 0.1743(3) 0.4226(13) 0.045(2) Uani 1 1 d . . . H20 H 1.2163 0.1567 0.5130 0.053 Uiso 1 1 calc R . . C21 C 1.2805(12) 0.1985(3) 0.3605(15) 0.053(3) Uani 1 1 d . . . H21 H 1.3891 0.1969 0.4089 0.064 Uiso 1 1 calc R . . C22 C 1.2275(12) 0.2247(3) 0.2307(15) 0.054(3) Uani 1 1 d . . . H22 H 1.2988 0.2410 0.1913 0.064 Uiso 1 1 calc R . . C23 C 1.0683(13) 0.2270(2) 0.1580(14) 0.051(3) Uani 1 1 d . . . H23 H 1.0304 0.2448 0.0682 0.061 Uiso 1 1 calc R . . C24 C 0.9638(11) 0.2027(2) 0.2189(13) 0.043(2) Uani 1 1 d . . . H24 H 0.8556 0.2044 0.1685 0.052 Uiso 1 1 calc R . . N1 N 0.6265(10) 0.0876(2) 0.5653(15) 0.061(2) Uani 1 1 d . . . Sb1 Sb 0.84402(7) 0.135195(15) 0.39952(9) 0.0358(2) Uani 1 1 d . . . C9 C 0.6465(17) 0.0501(3) 0.585(3) 0.104(5) Uani 1 1 d . . . H9A H 0.7502 0.0450 0.6586 0.156 Uiso 1 1 calc R . . H9B H 0.6367 0.0395 0.4553 0.156 Uiso 1 1 calc R . . H9C H 0.5660 0.0406 0.6552 0.156 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 C1 0.025(4) 0.039(5) 0.042(5) -0.002(4) 0.007(4) 0.004(4) C2 0.040(5) 0.047(6) 0.066(7) 0.005(5) 0.024(5) -0.004(4) C3 0.045(6) 0.088(9) 0.061(7) 0.016(6) 0.031(5) 0.012(6) C4 0.047(6) 0.071(7) 0.047(6) -0.010(5) 0.009(5) 0.019(5) C5 0.055(6) 0.045(6) 0.060(7) -0.006(5) 0.009(5) 0.010(5) C6 0.038(5) 0.047(6) 0.044(5) -0.001(4) 0.004(4) 0.000(4) C7 0.082(9) 0.052(7) 0.090(9) 0.024(6) 0.037(7) 0.006(6) C8 0.061(8) 0.109(11) 0.130(13) -0.014(10) 0.019(8) -0.025(8) C10 0.032(4) 0.028(4) 0.035(5) 0.000(4) 0.014(4) 0.002(3) C11 0.033(5) 0.042(5) 0.037(5) 0.008(4) 0.011(4) 0.002(4) C12 0.046(6) 0.059(6) 0.038(5) 0.011(5) 0.006(4) -0.001(5) C13 0.043(6) 0.047(6) 0.070(7) 0.018(5) 0.011(5) 0.007(5) C14 0.046(6) 0.037(5) 0.079(8) 0.002(5) 0.027(5) 0.006(4) C15 0.035(5) 0.035(5) 0.047(5) 0.003(4) 0.018(4) -0.004(4) C16 0.051(6) 0.053(6) 0.035(5) -0.004(4) -0.007(4) 0.009(4) C17 0.069(9) 0.093(10) 0.099(10) 0.030(8) -0.012(7) 0.019(7) C18 0.085(8) 0.045(6) 0.055(6) -0.008(5) 0.025(6) -0.008(5) C19 0.042(5) 0.035(5) 0.029(4) 0.003(4) 0.011(4) 0.002(4) C20 0.042(5) 0.051(6) 0.039(5) 0.007(4) 0.002(4) 0.005(4) C21 0.039(5) 0.065(7) 0.056(6) 0.000(5) 0.007(5) -0.005(5) C22 0.057(7) 0.051(6) 0.057(6) -0.003(5) 0.021(5) -0.010(5) C23 0.072(7) 0.041(5) 0.046(6) 0.010(4) 0.027(5) 0.015(5) C24 0.039(5) 0.054(6) 0.038(5) -0.006(4) 0.006(4) 0.014(4) N1 0.046(5) 0.048(5) 0.093(7) -0.002(5) 0.024(5) -0.011(4) Sb1 0.0327(3) 0.0383(3) 0.0357(3) -0.0003(3) 0.0031(2) 0.0003(3) C9 0.104(11) 0.051(7) 0.176(16) 0.004(9) 0.082(11) -0.008(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 C1 C6 1.371(12) . ? C1 C2 1.402(12) . ? C1 Sb1 2.166(8) . ? C2 C3 1.380(13) . ? C2 C7 1.522(14) . ? C3 C4 1.364(15) . ? C3 H3 0.9300 . ? C4 C5 1.358(14) . ? C4 H4 0.9300 . ? C5 C6 1.381(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.426(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.462(10) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.3952 . ? C10 C15 1.410(10) . ? C10 Sb1 2.149(5) . ? C11 C12 1.4038(17) . ? C11 C16 1.502(10) . ? C12 C13 1.353(11) . ? C12 H12 0.9300 . ? C13 C14 1.368(14) . ? C13 C17 1.524(14) . ? C14 C15 1.382(13) . ? C14 H14 0.9300 . ? C15 C18 1.522(13) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.382(12) . ? C19 C20 1.385(12) . ? C19 Sb1 2.165(8) . ? C20 C21 1.379(13) . ? C20 H20 0.9300 . ? C21 C22 1.352(14) . ? C21 H21 0.9300 . ? C22 C23 1.367(14) . ? C22 H22 0.9300 . ? C23 C24 1.384(13) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? N1 C9 1.430(14) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 C6 C1 C2 117.4(8) . . ? C6 C1 Sb1 120.4(6) . . ? C2 C1 Sb1 122.0(6) . . ? C3 C2 C1 119.9(9) . . ? C3 C2 C7 118.3(9) . . ? C1 C2 C7 121.6(8) . . ? C4 C3 C2 120.8(10) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.5(9) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.9(10) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 122.5(9) . . ? C1 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? N1 C7 C2 113.5(9) . . ? N1 C7 H7A 108.9 . . ? C2 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C10 C15 117.6(4) . . ? C11 C10 Sb1 125.47(17) . . ? C15 C10 Sb1 116.9(5) . . ? C10 C11 C12 118.92(12) . . ? C10 C11 C16 123.3(4) . . ? C12 C11 C16 117.8(4) . . ? C13 C12 C11 123.8(5) . . ? C13 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? C12 C13 C14 116.6(8) . . ? C12 C13 C17 121.6(10) . . ? C14 C13 C17 121.8(10) . . ? C13 C14 C15 123.0(9) . . ? C13 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C14 C15 C10 120.0(8) . . ? C14 C15 C18 118.5(9) . . ? C10 C15 C18 121.5(7) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 116.6(8) . . ? C24 C19 Sb1 117.9(6) . . ? C20 C19 Sb1 124.9(6) . . ? C21 C20 C19 121.0(9) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 121.3(9) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 119.5(9) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 119.5(9) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C19 C24 C23 122.2(9) . . ? C19 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? C7 N1 C9 113.1(10) . . ? C7 N1 C8 110.6(9) . . ? C9 N1 C8 109.0(10) . . ? C10 Sb1 C19 96.5(3) . . ? C10 Sb1 C1 102.8(3) . . ? C19 Sb1 C1 98.2(3) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.923 _refine_diff_density_min -2.624 _refine_diff_density_rms 0.122 # Attachment 'Compound 4 - CCDC - 752092.cif' data_78richy _database_code_depnum_ccdc_archive 'CCDC 752092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N Sb' _chemical_formula_sum 'C21 H22 N Sb' _chemical_formula_weight 410.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.452(3) _cell_length_b 35.081(12) _cell_length_c 6.335(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.200(6) _cell_angle_gamma 90.00 _cell_volume 1870.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5271 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 24.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5832 _exptl_absorpt_correction_T_max 0.8546 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14969 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3817 _reflns_number_gt 3516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0358P)^2^+2.1183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3817 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.85059(3) 0.119059(7) -0.03897(4) 0.04402(11) Uani 1 1 d . . . N1 N 0.6151(4) 0.07662(10) 0.1538(6) 0.0582(9) Uani 1 1 d . . . C1 C 0.7336(4) 0.15516(10) 0.1766(6) 0.0416(8) Uani 1 1 d . . . C6 C 0.7595(5) 0.19388(11) 0.1810(7) 0.0502(9) Uani 1 1 d . . . H6 H 0.8330 0.2041 0.0962 0.060 Uiso 1 1 calc R . . C5 C 0.6796(6) 0.21810(13) 0.3076(7) 0.0592(11) Uani 1 1 d . . . H5 H 0.7008 0.2441 0.3093 0.071 Uiso 1 1 calc R . . C4 C 0.5696(6) 0.20340(14) 0.4297(8) 0.0639(12) Uani 1 1 d . . . H4 H 0.5119 0.2196 0.5103 0.077 Uiso 1 1 calc R . . C3 C 0.5442(6) 0.16506(15) 0.4337(8) 0.0689(13) Uani 1 1 d . . . H3 H 0.4716 0.1552 0.5211 0.083 Uiso 1 1 calc R . . C2 C 0.6243(5) 0.14068(13) 0.3105(8) 0.0577(11) Uani 1 1 d . . . C7 C 0.6060(7) 0.09757(16) 0.3424(9) 0.0764(14) Uani 1 1 d . . . H7A H 0.6887 0.0889 0.4475 0.092 Uiso 1 1 calc R . . H7B H 0.5043 0.0926 0.3969 0.092 Uiso 1 1 calc R . . C8 C 0.6295(8) 0.03659(15) 0.1778(13) 0.104(2) Uani 1 1 d . . . H8A H 0.7228 0.0308 0.2702 0.157 Uiso 1 1 calc R . . H8B H 0.6381 0.0251 0.0418 0.157 Uiso 1 1 calc R . . H8C H 0.5375 0.0268 0.2377 0.157 Uiso 1 1 calc R . . C9 C 0.4719(7) 0.08379(19) 0.0006(11) 0.0935(19) Uani 1 1 d . . . H9A H 0.4831 0.0703 -0.1289 0.140 Uiso 1 1 calc R . . H9B H 0.4628 0.1106 -0.0283 0.140 Uiso 1 1 calc R . . H9C H 0.3783 0.0751 0.0612 0.140 Uiso 1 1 calc R . . C10 C 1.0022(4) 0.08868(11) 0.1950(6) 0.0445(9) Uani 1 1 d . . . C11 C 1.0526(5) 0.10439(13) 0.3892(7) 0.0565(10) Uani 1 1 d . . . H11 H 1.0233 0.1292 0.4191 0.068 Uiso 1 1 calc R . . C12 C 1.1454(5) 0.08411(16) 0.5396(7) 0.0681(13) Uani 1 1 d . . . H12 H 1.1806 0.0955 0.6679 0.082 Uiso 1 1 calc R . . C13 C 1.1862(6) 0.04697(16) 0.5002(9) 0.0760(15) Uani 1 1 d . . . H13 H 1.2460 0.0328 0.6029 0.091 Uiso 1 1 calc R . . C14 C 1.1375(6) 0.03108(14) 0.3073(10) 0.0757(15) Uani 1 1 d . . . H14 H 1.1662 0.0061 0.2787 0.091 Uiso 1 1 calc R . . C15 C 1.0462(5) 0.05169(12) 0.1547(8) 0.0586(11) Uani 1 1 d . . . H15 H 1.0143 0.0405 0.0245 0.070 Uiso 1 1 calc R . . C16 C 1.0241(4) 0.16196(11) -0.1072(6) 0.0441(9) Uani 1 1 d . . . C17 C 0.9817(5) 0.18634(13) -0.2738(7) 0.0558(10) Uani 1 1 d . . . H17 H 0.8820 0.1838 -0.3475 0.067 Uiso 1 1 calc R . . C18 C 1.0828(6) 0.21431(13) -0.3340(7) 0.0621(12) Uani 1 1 d . . . H18 H 1.0505 0.2306 -0.4457 0.075 Uiso 1 1 calc R . . C19 C 1.2305(6) 0.21813(14) -0.2295(8) 0.0633(12) Uani 1 1 d . . . H19 H 1.2990 0.2371 -0.2692 0.076 Uiso 1 1 calc R . . C20 C 1.2770(5) 0.19405(14) -0.0668(8) 0.0650(12) Uani 1 1 d . . . H20 H 1.3782 0.1963 0.0031 0.078 Uiso 1 1 calc R . . C21 C 1.1751(5) 0.16632(13) -0.0050(7) 0.0566(11) Uani 1 1 d . . . H21 H 1.2082 0.1503 0.1072 0.068 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 Sb1 0.04397(16) 0.04519(17) 0.04201(16) -0.00417(11) -0.00091(11) -0.00201(11) N1 0.054(2) 0.049(2) 0.071(2) -0.0047(18) 0.0035(18) -0.0119(17) C1 0.0407(19) 0.043(2) 0.040(2) -0.0021(16) -0.0029(15) 0.0051(16) C6 0.053(2) 0.046(2) 0.052(2) 0.0016(18) 0.0039(18) -0.0010(18) C5 0.064(3) 0.047(2) 0.064(3) -0.008(2) -0.004(2) 0.009(2) C4 0.056(3) 0.067(3) 0.068(3) -0.015(2) 0.003(2) 0.016(2) C3 0.055(3) 0.079(3) 0.076(3) 0.001(3) 0.021(2) 0.000(2) C2 0.053(2) 0.051(2) 0.070(3) -0.001(2) 0.008(2) -0.003(2) C7 0.075(3) 0.082(4) 0.074(3) 0.004(3) 0.018(3) -0.020(3) C8 0.089(4) 0.055(3) 0.174(7) 0.001(4) 0.036(4) -0.016(3) C9 0.066(3) 0.105(5) 0.105(5) -0.002(4) -0.012(3) -0.020(3) C10 0.0396(19) 0.043(2) 0.052(2) 0.0003(17) 0.0073(16) 0.0052(16) C11 0.060(3) 0.056(2) 0.052(2) -0.002(2) 0.001(2) 0.015(2) C12 0.061(3) 0.090(4) 0.052(3) 0.004(2) -0.002(2) 0.016(3) C13 0.068(3) 0.075(3) 0.084(4) 0.026(3) 0.000(3) 0.016(3) C14 0.068(3) 0.045(3) 0.114(5) 0.009(3) 0.006(3) 0.016(2) C15 0.053(2) 0.046(2) 0.076(3) -0.007(2) 0.003(2) 0.0023(19) C16 0.041(2) 0.047(2) 0.045(2) -0.0050(17) 0.0064(16) 0.0015(16) C17 0.053(2) 0.065(3) 0.049(2) 0.002(2) 0.0046(19) -0.001(2) C18 0.071(3) 0.063(3) 0.055(3) 0.012(2) 0.015(2) -0.001(2) C19 0.058(3) 0.060(3) 0.075(3) -0.001(2) 0.025(2) -0.007(2) C20 0.045(2) 0.070(3) 0.080(3) -0.004(3) 0.007(2) -0.008(2) C21 0.049(2) 0.060(3) 0.060(3) 0.006(2) -0.0011(19) 0.005(2) _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 C10 2.152(4) . ? Sb1 C1 2.166(4) . ? Sb1 C16 2.172(4) . ? N1 C7 1.411(6) . ? N1 C8 1.417(6) . ? N1 C9 1.502(6) . ? C1 C6 1.376(5) . ? C1 C2 1.405(6) . ? C6 C5 1.385(6) . ? C6 H6 0.9300 . ? C5 C4 1.363(7) . ? C5 H5 0.9300 . ? C4 C3 1.363(7) . ? C4 H4 0.9300 . ? C3 C2 1.376(6) . ? C3 H3 0.9300 . ? C2 C7 1.535(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.380(5) . ? C10 C11 1.380(6) . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.376(7) . ? C12 H12 0.9300 . ? C13 C14 1.372(8) . ? C13 H13 0.9300 . ? C14 C15 1.385(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.380(6) . ? C16 C21 1.386(5) . ? C17 C18 1.377(6) . ? C17 H17 0.9300 . ? C18 C19 1.366(7) . ? C18 H18 0.9300 . ? C19 C20 1.363(7) . ? C19 H19 0.9300 . ? C20 C21 1.379(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Sb1 C1 97.62(14) . . ? C10 Sb1 C16 96.29(15) . . ? C1 Sb1 C16 94.33(14) . . ? C7 N1 C8 115.9(5) . . ? C7 N1 C9 110.9(4) . . ? C8 N1 C9 107.0(5) . . ? C6 C1 C2 117.2(4) . . ? C6 C1 Sb1 120.6(3) . . ? C2 C1 Sb1 122.2(3) . . ? C1 C6 C5 122.2(4) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C3 C2 121.1(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C2 C1 120.1(4) . . ? C3 C2 C7 118.5(4) . . ? C1 C2 C7 121.0(4) . . ? N1 C7 C2 112.8(4) . . ? N1 C7 H7A 109.0 . . ? C2 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.3(4) . . ? C15 C10 Sb1 119.5(3) . . ? C11 C10 Sb1 122.2(3) . . ? C12 C11 C10 121.4(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.1(4) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 120.9(5) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 120.3(5) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C21 116.9(4) . . ? C17 C16 Sb1 116.6(3) . . ? C21 C16 Sb1 126.4(3) . . ? C18 C17 C16 121.9(4) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C19 C18 C17 119.9(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C16 121.2(4) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? 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 Sb1 C1 C6 112.3(3) . . . . ? C16 Sb1 C1 C6 15.4(3) . . . . ? C10 Sb1 C1 C2 -70.4(3) . . . . ? C16 Sb1 C1 C2 -167.3(3) . . . . ? C2 C1 C6 C5 -1.4(6) . . . . ? Sb1 C1 C6 C5 176.1(3) . . . . ? C1 C6 C5 C4 -1.1(7) . . . . ? C6 C5 C4 C3 2.9(7) . . . . ? C5 C4 C3 C2 -2.2(8) . . . . ? C4 C3 C2 C1 -0.4(8) . . . . ? C4 C3 C2 C7 172.5(5) . . . . ? C6 C1 C2 C3 2.1(6) . . . . ? Sb1 C1 C2 C3 -175.3(4) . . . . ? C6 C1 C2 C7 -170.6(4) . . . . ? Sb1 C1 C2 C7 12.0(6) . . . . ? C8 N1 C7 C2 168.5(4) . . . . ? C9 N1 C7 C2 -69.3(5) . . . . ? C3 C2 C7 N1 147.9(5) . . . . ? C1 C2 C7 N1 -39.2(6) . . . . ? C1 Sb1 C10 C15 150.0(3) . . . . ? C16 Sb1 C10 C15 -114.8(3) . . . . ? C1 Sb1 C10 C11 -27.4(4) . . . . ? C16 Sb1 C10 C11 67.8(4) . . . . ? C15 C10 C11 C12 0.5(7) . . . . ? Sb1 C10 C11 C12 177.9(4) . . . . ? C10 C11 C12 C13 -1.8(8) . . . . ? C11 C12 C13 C14 2.1(8) . . . . ? C12 C13 C14 C15 -1.1(8) . . . . ? C11 C10 C15 C14 0.5(7) . . . . ? Sb1 C10 C15 C14 -177.0(4) . . . . ? C13 C14 C15 C10 -0.2(8) . . . . ? C10 Sb1 C16 C17 172.8(3) . . . . ? C1 Sb1 C16 C17 -89.0(3) . . . . ? C10 Sb1 C16 C21 -4.6(4) . . . . ? C1 Sb1 C16 C21 93.5(4) . . . . ? C21 C16 C17 C18 -1.3(6) . . . . ? Sb1 C16 C17 C18 -179.0(3) . . . . ? C16 C17 C18 C19 0.9(7) . . . . ? C17 C18 C19 C20 0.3(7) . . . . ? C18 C19 C20 C21 -1.1(7) . . . . ? C19 C20 C21 C16 0.6(7) . . . . ? C17 C16 C21 C20 0.5(6) . . . . ? Sb1 C16 C21 C20 178.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.840 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.075