# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ales Ruzicka' _publ_contact_author_email ales.ruzicka@upce.cz loop_ _publ_author_name P.Simon R.Jambor A.Ruzicka A.Lycka 'F.De Proft' L.Dostal # Attachment '- compound 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 846899' #TrackingRef '- compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H27 N2 Sb Se' _chemical_formula_sum 'C26 H27 N2 Sb Se' _chemical_formula_weight 568.21 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' Se Se -0.0929 2.2259 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.0599(7) _cell_length_b 12.2821(11) _cell_length_c 16.2390(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2405.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18542 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 2.675 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.132 0 -1 0 0.095 0 0 1 0.314 0 0 -1 0.195 1 0 0 0.096 -1 0 0 0.118 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.450 _exptl_absorpt_correction_T_max 0.598 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18494 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5480 _reflns_number_gt 4934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0171P)^2^+1.7690P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(9) _refine_ls_number_reflns 5480 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Sb1 Sb 0.679994(15) 0.495610(17) 0.900326(10) 0.01886(5) Uani 1 1 d . . . Se1 Se 0.73510(3) 0.31881(3) 0.84657(2) 0.02806(8) Uani 1 1 d . . . N1 N 0.4879(2) 0.4474(2) 0.90836(15) 0.0190(5) Uani 1 1 d . . . C1 C 0.6412(3) 0.4702(2) 1.02647(18) 0.0226(7) Uani 1 1 d . . . N2 N 0.8443(2) 0.5327(2) 0.97807(16) 0.0258(6) Uani 1 1 d . . . C23 C 1.0264(3) 0.5055(4) 0.9144(2) 0.0393(8) Uani 1 1 d . . . C8 C 0.4205(2) 0.4387(2) 0.8365(2) 0.0204(6) Uani 1 1 d . . . C7 C 0.4512(3) 0.4298(3) 0.98180(19) 0.0234(7) Uani 1 1 d . . . C18 C 0.9426(3) 0.5750(3) 0.9388(2) 0.0321(8) Uani 1 1 d . . . C13 C 0.3886(3) 0.3363(3) 0.8070(2) 0.0248(7) Uani 1 1 d . . . C6 C 0.7211(3) 0.4910(3) 1.08589(17) 0.0268(6) Uani 1 1 d . . . C10 C 0.3355(3) 0.5264(3) 0.7209(2) 0.0304(7) Uani 1 1 d . . . H10 H 0.3197 0.5890 0.6909 0.036 Uiso 1 1 d R . . C9 C 0.3946(3) 0.5347(2) 0.79361(19) 0.0216(6) Uani 1 1 d . . . C19 C 0.9447(3) 0.6871(3) 0.9213(3) 0.0449(10) Uani 1 1 d . . . C20 C 1.0356(4) 0.7256(4) 0.8762(3) 0.0626(15) Uani 1 1 d . . . H20 H 1.0399 0.7992 0.8631 0.075 Uiso 1 1 d R . . C2 C 0.5338(3) 0.4404(3) 1.04847(19) 0.0264(7) Uani 1 1 d . . . C5 C 0.6937(3) 0.4787(3) 1.16904(19) 0.0354(8) Uani 1 1 d . . . H5 H 0.7458 0.4940 1.2096 0.042 Uiso 1 1 d R . . C17 C 0.8303(3) 0.5296(2) 1.05672(19) 0.0268(7) Uani 1 1 d . . . C16 C 0.4185(3) 0.2335(3) 0.8518(2) 0.0323(8) Uani 1 1 d . . . H16A H 0.3707 0.2251 0.8987 0.039 Uiso 1 1 d R . . H16B H 0.4096 0.1724 0.8156 0.039 Uiso 1 1 d R . . H16C H 0.4942 0.2375 0.8699 0.039 Uiso 1 1 d R . . C14 C 0.3335(3) 0.4034(3) 1.0021(2) 0.0327(8) Uani 1 1 d . . . H14A H 0.2911 0.3982 0.9522 0.039 Uiso 1 1 d R . . H14B H 0.3305 0.3352 1.0309 0.039 Uiso 1 1 d R . . H14C H 0.3032 0.4598 1.0363 0.039 Uiso 1 1 d R . . C4 C 0.5883(4) 0.4444(3) 1.1909(2) 0.0409(10) Uani 1 1 d . . . H4 H 0.5715 0.4335 1.2462 0.049 Uiso 1 1 d R . . C11 C 0.3023(4) 0.4261(3) 0.6919(2) 0.0404(10) Uani 1 1 d . . . H11 H 0.2614 0.4218 0.6435 0.049 Uiso 1 1 d R . . C12 C 0.3279(3) 0.3324(3) 0.7349(2) 0.0350(8) Uani 1 1 d . . . H12 H 0.3037 0.2655 0.7151 0.042 Uiso 1 1 d R . . C3 C 0.5082(3) 0.4259(3) 1.1318(2) 0.0360(9) Uani 1 1 d . . . H3 H 0.4374 0.4039 1.1473 0.043 Uiso 1 1 d R . . C24 C 0.9172(4) 0.5658(3) 1.1169(2) 0.0429(10) Uani 1 1 d . . . H24A H 0.9743 0.6047 1.0881 0.052 Uiso 1 1 d R . . H24B H 0.8843 0.6125 1.1575 0.052 Uiso 1 1 d R . . H24C H 0.9487 0.5033 1.1435 0.052 Uiso 1 1 d R . . C15 C 0.4249(3) 0.6447(3) 0.8271(2) 0.0295(8) Uani 1 1 d . . . H15A H 0.3972 0.7001 0.7907 0.035 Uiso 1 1 d R . . H15B H 0.3928 0.6541 0.8807 0.035 Uiso 1 1 d R . . H15C H 0.5041 0.6505 0.8309 0.035 Uiso 1 1 d R . . C21 C 1.1177(4) 0.6574(5) 0.8502(4) 0.0726(17) Uani 1 1 d . . . H21 H 1.1776 0.6855 0.8211 0.087 Uiso 1 1 d R . . C26 C 1.0241(3) 0.3868(3) 0.9352(3) 0.0445(10) Uani 1 1 d . . . H26A H 1.0679 0.3475 0.8958 0.053 Uiso 1 1 d R . . H26B H 1.0537 0.3756 0.9894 0.053 Uiso 1 1 d R . . H26C H 0.9490 0.3612 0.9333 0.053 Uiso 1 1 d R . . C25 C 0.8534(4) 0.7600(3) 0.9512(3) 0.0572(14) Uani 1 1 d . . . H25A H 0.8693 0.8340 0.9362 0.069 Uiso 1 1 d R . . H25B H 0.7847 0.7379 0.9264 0.069 Uiso 1 1 d R . . H25C H 0.8474 0.7546 1.0100 0.069 Uiso 1 1 d R . . C22 C 1.1130(3) 0.5489(4) 0.8685(3) 0.0559(13) Uani 1 1 d . . . H22 H 1.1678 0.5027 0.8483 0.067 Uiso 1 1 d 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 0.01969(8) 0.02121(9) 0.01569(8) 0.00119(9) -0.00167(7) -0.00100(10) Se1 0.02964(17) 0.02598(16) 0.02854(17) -0.00577(13) -0.00145(15) 0.00315(14) N1 0.0199(12) 0.0187(12) 0.0183(13) 0.0018(10) -0.0027(11) -0.0005(10) C1 0.0289(16) 0.0222(16) 0.0167(13) -0.0021(11) -0.0004(12) 0.0058(12) N2 0.0247(15) 0.0236(13) 0.0292(14) 0.0011(10) -0.0092(11) -0.0018(10) C23 0.0226(15) 0.051(2) 0.0441(19) 0.019(2) -0.0065(14) -0.003(2) C8 0.0189(15) 0.0232(16) 0.0192(15) 0.0041(13) 0.0013(13) -0.0009(12) C7 0.0256(17) 0.0198(15) 0.0247(16) -0.0002(12) 0.0034(13) 0.0035(13) C18 0.0295(19) 0.0333(19) 0.0335(19) 0.0099(15) -0.0180(15) -0.0126(15) C13 0.0246(17) 0.0225(16) 0.0274(16) 0.0018(13) -0.0032(13) -0.0039(14) C6 0.0353(15) 0.0236(15) 0.0217(14) -0.0004(13) -0.0047(12) 0.0072(16) C10 0.0350(19) 0.0260(17) 0.0301(16) 0.0059(12) -0.0082(14) 0.0025(14) C9 0.0208(15) 0.0208(15) 0.0233(15) 0.0001(11) 0.0028(12) 0.0018(12) C19 0.047(2) 0.035(2) 0.053(2) 0.0134(17) -0.0322(19) -0.0187(19) C20 0.063(3) 0.053(3) 0.072(3) 0.037(2) -0.035(3) -0.035(3) C2 0.0319(18) 0.0276(17) 0.0195(15) 0.0024(13) 0.0028(14) 0.0070(14) C5 0.048(2) 0.040(2) 0.0183(14) -0.0065(13) -0.0110(14) 0.0119(17) C17 0.0352(18) 0.0154(14) 0.0298(16) -0.0018(11) -0.0125(15) 0.0026(13) C16 0.038(2) 0.0221(16) 0.0369(19) 0.0050(15) -0.0064(17) -0.0051(14) C14 0.0268(19) 0.043(2) 0.0287(17) 0.0067(14) 0.0084(15) -0.0006(16) C4 0.051(3) 0.056(2) 0.0152(16) 0.0014(16) 0.0048(16) 0.014(2) C11 0.050(3) 0.0341(18) 0.038(2) -0.0027(15) -0.0237(18) -0.0027(18) C12 0.039(2) 0.0245(16) 0.0411(19) -0.0026(14) -0.0147(17) -0.0037(17) C3 0.037(2) 0.049(2) 0.0222(17) 0.0059(16) 0.0050(15) 0.0077(18) C24 0.057(3) 0.033(2) 0.039(2) 0.0039(16) -0.0274(19) -0.0057(18) C15 0.035(2) 0.0223(17) 0.0313(19) 0.0021(14) -0.0053(15) 0.0014(14) C21 0.033(2) 0.098(4) 0.087(4) 0.051(3) -0.018(3) -0.025(3) C26 0.024(2) 0.050(3) 0.059(3) 0.012(2) 0.0050(18) 0.0063(18) C25 0.079(4) 0.026(2) 0.066(3) 0.0011(19) -0.042(3) -0.005(2) C22 0.0211(19) 0.083(3) 0.064(3) 0.036(2) -0.0038(18) -0.010(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 C1 2.124(3) . ? Sb1 N2 2.394(3) . ? Sb1 N1 2.395(2) . ? Sb1 Se1 2.4329(4) . ? N1 C7 1.290(4) . ? N1 C8 1.426(4) . ? C1 C6 1.388(4) . ? C1 C2 1.392(5) . ? N2 C17 1.289(4) . ? N2 C18 1.442(5) . ? C23 C18 1.381(6) . ? C23 C22 1.389(5) . ? C23 C26 1.497(6) . ? C8 C13 1.400(4) . ? C8 C9 1.404(4) . ? C7 C2 1.477(5) . ? C7 C14 1.493(5) . ? C18 C19 1.407(5) . ? C13 C12 1.381(5) . ? C13 C16 1.501(4) . ? C6 C5 1.399(4) . ? C6 C17 1.477(5) . ? C10 C11 1.378(5) . ? C10 C9 1.383(4) . ? C10 H10 0.9300 . ? C9 C15 1.502(4) . ? C19 C20 1.401(7) . ? C19 C25 1.500(7) . ? C20 C21 1.363(8) . ? C20 H20 0.9301 . ? C2 C3 1.400(5) . ? C5 C4 1.384(6) . ? C5 H5 0.9299 . ? C17 C24 1.500(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9599 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C4 C3 1.380(5) . ? C4 H4 0.9301 . ? C11 C12 1.380(5) . ? C11 H11 0.9299 . ? C12 H12 0.9300 . ? C3 H3 0.9301 . ? C24 H24A 0.9600 . ? C24 H24B 0.9601 . ? C24 H24C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C21 C22 1.367(7) . ? C21 H21 0.9299 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C22 H22 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 C1 Sb1 N2 72.66(11) . . ? C1 Sb1 N1 72.41(11) . . ? N2 Sb1 N1 145.02(9) . . ? C1 Sb1 Se1 105.97(8) . . ? N2 Sb1 Se1 97.65(6) . . ? N1 Sb1 Se1 93.61(6) . . ? C7 N1 C8 123.3(3) . . ? C7 N1 Sb1 115.0(2) . . ? C8 N1 Sb1 121.67(18) . . ? C6 C1 C2 121.1(3) . . ? C6 C1 Sb1 119.3(2) . . ? C2 C1 Sb1 119.4(2) . . ? C17 N2 C18 123.8(3) . . ? C17 N2 Sb1 114.1(2) . . ? C18 N2 Sb1 121.0(2) . . ? C18 C23 C22 117.9(4) . . ? C18 C23 C26 121.5(3) . . ? C22 C23 C26 120.6(4) . . ? C13 C8 C9 121.5(3) . . ? C13 C8 N1 120.3(3) . . ? C9 C8 N1 118.1(3) . . ? N1 C7 C2 115.6(3) . . ? N1 C7 C14 124.5(3) . . ? C2 C7 C14 119.9(3) . . ? C23 C18 C19 122.3(4) . . ? C23 C18 N2 120.4(3) . . ? C19 C18 N2 117.1(4) . . ? C12 C13 C8 117.8(3) . . ? C12 C13 C16 120.6(3) . . ? C8 C13 C16 121.5(3) . . ? C1 C6 C5 119.1(3) . . ? C1 C6 C17 117.1(3) . . ? C5 C6 C17 123.7(3) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 119.5 . . ? C10 C9 C8 118.5(3) . . ? C10 C9 C15 120.0(3) . . ? C8 C9 C15 121.4(3) . . ? C20 C19 C18 116.7(4) . . ? C20 C19 C25 122.9(4) . . ? C18 C19 C25 120.4(4) . . ? C21 C20 C19 121.5(4) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.4 . . ? C1 C2 C3 119.1(3) . . ? C1 C2 C7 117.5(3) . . ? C3 C2 C7 123.3(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.2 . . ? N2 C17 C6 116.4(3) . . ? N2 C17 C24 123.0(3) . . ? C6 C17 C24 120.6(3) . . ? C13 C16 H16A 109.4 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 C14 H14A 109.6 . . ? C7 C14 H14B 109.4 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.4 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.4 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 121.2(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.3 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.0 . . ? C17 C24 H24A 109.4 . . ? C17 C24 H24B 109.6 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.4 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 C15 H15A 109.3 . . ? C9 C15 H15B 109.8 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.4 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C20 C21 C22 120.1(4) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 120.3 . . ? C23 C26 H26A 109.2 . . ? C23 C26 H26B 109.9 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.3 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C25 H25A 109.6 . . ? C19 C25 H25B 109.2 . . ? H25A C25 H25B 109.5 . . ? C19 C25 H25C 109.6 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 C22 C23 121.4(5) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.375 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.076 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 846900' #TrackingRef '- compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H27 N2 S Sb' _chemical_formula_sum 'C26 H27 N2 S Sb' _chemical_formula_weight 521.31 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' S S 0.1246 0.1234 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.1292(7) _cell_length_b 12.1288(17) _cell_length_c 16.2089(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2384.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 17069 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.259 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 -1 0 0.037 -1 1 0 0.180 1 1 0 0.170 -1 -1 0 0.068 0 0 1 0.021 0 0 -1 0.041 -1 0 0 0.113 1 0 0 0.126 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17042 _diffrn_reflns_av_R_equivalents 0.1030 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5391 _reflns_number_gt 4828 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0115P)^2^+5.9150P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(1) _refine_ls_number_reflns 5391 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 0.68012(3) 0.98994(3) 0.89647(2) 0.02431(10) Uani 1 1 d . . . S1 S 0.72921(13) 0.81894(14) 0.84864(10) 0.0343(4) Uani 1 1 d . . . N1 N 0.8453(4) 1.0281(4) 0.9746(3) 0.0298(11) Uani 1 1 d . . . C1 C 0.6412(5) 0.9692(5) 1.0232(3) 0.0264(12) Uani 1 1 d . . . C19 C 0.3891(4) 0.8339(5) 0.8037(4) 0.0280(13) Uani 1 1 d . . . C18 C 0.4193(4) 0.9368(5) 0.8330(4) 0.0250(12) Uani 1 1 d . . . N2 N 0.4865(3) 0.9450(4) 0.9064(3) 0.0232(9) Uani 1 1 d . . . C4 C 0.5879(6) 0.9510(7) 1.1891(4) 0.0485(19) Uani 1 1 d . . . H4 H 0.5712 0.9422 1.2448 0.058 Uiso 1 1 d R . . C22 C 0.3375(5) 1.0265(5) 0.7179(4) 0.0347(13) Uani 1 1 d . . . H22 H 0.3209 1.0904 0.6887 0.042 Uiso 1 1 d R . . C17 C 0.4503(5) 0.9284(5) 0.9795(4) 0.0308(13) Uani 1 1 d . . . C2 C 0.7211(5) 0.9920(6) 1.0827(3) 0.0350(13) Uani 1 1 d . . . C25 C 0.4186(5) 0.7300(5) 0.8477(4) 0.0335(13) Uani 1 1 d . . . H25A H 0.3705 0.7205 0.8941 0.040 Uiso 1 1 d R . . H25B H 0.4103 0.6687 0.8107 0.040 Uiso 1 1 d R . . H25C H 0.4936 0.7336 0.8665 0.040 Uiso 1 1 d R . . C23 C 0.3938(4) 1.0337(5) 0.7914(3) 0.0271(12) Uani 1 1 d . . . C8 C 0.9441(5) 1.0696(6) 0.9342(4) 0.0391(16) Uani 1 1 d . . . C6 C 0.5333(5) 0.9405(5) 1.0470(4) 0.0313(13) Uani 1 1 d . . . C7 C 0.8303(5) 1.0292(5) 1.0527(4) 0.0356(13) Uani 1 1 d . . . C13 C 1.0261(4) 0.9954(6) 0.9083(4) 0.0406(14) Uani 1 1 d . . . C24 C 0.3328(5) 0.9009(6) 1.0001(4) 0.0373(14) Uani 1 1 d . . . H24A H 0.2923 0.8900 0.9499 0.045 Uiso 1 1 d R . . H24B H 0.3301 0.8348 1.0327 0.045 Uiso 1 1 d R . . H24C H 0.3008 0.9607 1.0307 0.045 Uiso 1 1 d R . . C14 C 0.9174(6) 1.0672(6) 1.1131(5) 0.0482(18) Uani 1 1 d . . . H14A H 0.9783 1.0980 1.0832 0.058 Uiso 1 1 d R . . H14B H 0.8868 1.1222 1.1490 0.058 Uiso 1 1 d R . . H14C H 0.9424 1.0057 1.1453 0.058 Uiso 1 1 d R . . C26 C 0.4224(5) 1.1450(5) 0.8269(4) 0.0340(15) Uani 1 1 d . . . H26A H 0.3856 1.1542 0.8789 0.041 Uiso 1 1 d R . . H26B H 0.5006 1.1498 0.8350 0.041 Uiso 1 1 d R . . H26C H 0.3991 1.2018 0.7896 0.041 Uiso 1 1 d R . . C21 C 0.3058(6) 0.9251(6) 0.6876(5) 0.0455(17) Uani 1 1 d . . . H21 H 0.2678 0.9208 0.6379 0.055 Uiso 1 1 d R . . C20 C 0.3301(6) 0.8300(5) 0.7302(4) 0.0385(14) Uani 1 1 d . . . H20 H 0.3065 0.7622 0.7100 0.046 Uiso 1 1 d R . . C3 C 0.6933(6) 0.9846(6) 1.1657(3) 0.0446(16) Uani 1 1 d . . . H3 H 0.7447 1.0023 1.2062 0.054 Uiso 1 1 d R . . C9 C 0.9491(6) 1.1824(6) 0.9175(5) 0.048(2) Uani 1 1 d . . . C5 C 0.5077(6) 0.9293(7) 1.1299(4) 0.0420(17) Uani 1 1 d . . . H5 H 0.4371 0.9083 1.1458 0.050 Uiso 1 1 d R . . C10 C 1.0401(7) 1.2207(7) 0.8710(6) 0.065(3) Uani 1 1 d . . . H10 H 1.0452 1.2954 0.8584 0.078 Uiso 1 1 d R . . C12 C 1.1128(6) 1.0393(8) 0.8618(5) 0.060(2) Uani 1 1 d . . . H12 H 1.1668 0.9918 0.8419 0.072 Uiso 1 1 d R . . C15 C 0.8600(7) 1.2586(6) 0.9471(5) 0.062(2) Uani 1 1 d . . . H15A H 0.8531 1.2523 1.0059 0.075 Uiso 1 1 d R . . H15B H 0.8783 1.3332 0.9328 0.075 Uiso 1 1 d R . . H15C H 0.7915 1.2387 0.9215 0.075 Uiso 1 1 d R . . C16 C 1.0200(6) 0.8759(7) 0.9285(5) 0.0480(19) Uani 1 1 d . . . H16A H 0.9459 0.8503 0.9202 0.058 Uiso 1 1 d R . . H16B H 1.0691 0.8358 0.8929 0.058 Uiso 1 1 d R . . H16C H 1.0410 0.8642 0.9849 0.058 Uiso 1 1 d R . . C11 C 1.1204(6) 1.1489(8) 0.8435(6) 0.069(3) Uani 1 1 d . . . H11 H 1.1795 1.1760 0.8131 0.083 Uiso 1 1 d 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 0.02267(15) 0.02666(17) 0.02362(15) 0.00072(15) -0.00190(14) -0.00113(15) S1 0.0304(7) 0.0326(9) 0.0397(8) -0.0083(7) -0.0004(7) 0.0013(6) N1 0.031(2) 0.021(2) 0.038(3) 0.002(2) -0.0100(19) 0.0019(19) C1 0.033(3) 0.021(3) 0.025(2) -0.003(2) 0.000(2) 0.006(2) C19 0.020(3) 0.032(3) 0.033(3) 0.007(3) 0.000(2) -0.003(2) C18 0.017(2) 0.031(3) 0.028(3) 0.000(2) 0.000(2) 0.000(2) N2 0.023(2) 0.023(2) 0.024(2) 0.0039(19) -0.0012(19) 0.0004(17) C4 0.063(4) 0.064(5) 0.018(3) -0.001(3) 0.002(3) 0.016(4) C22 0.035(3) 0.030(3) 0.038(3) 0.006(3) -0.010(2) 0.004(3) C17 0.029(3) 0.030(3) 0.034(3) 0.001(3) 0.004(3) 0.007(3) C2 0.042(3) 0.030(3) 0.033(3) -0.010(3) -0.008(2) 0.009(3) C25 0.039(3) 0.021(3) 0.041(3) 0.005(3) -0.005(3) -0.001(3) C23 0.021(2) 0.028(3) 0.032(3) -0.002(2) -0.004(2) -0.003(2) C8 0.031(3) 0.037(4) 0.049(4) 0.013(3) -0.018(3) -0.011(3) C6 0.037(3) 0.031(3) 0.026(3) -0.002(2) 0.000(3) 0.012(3) C7 0.041(3) 0.026(3) 0.039(3) -0.001(2) -0.021(3) 0.006(3) C13 0.021(2) 0.046(4) 0.055(4) 0.010(4) -0.009(2) -0.003(3) C24 0.029(3) 0.045(4) 0.037(3) 0.003(3) 0.008(3) 0.002(3) C14 0.065(4) 0.031(4) 0.049(4) 0.007(3) -0.030(4) -0.004(3) C26 0.037(4) 0.023(3) 0.042(4) -0.002(3) -0.007(3) 0.002(3) C21 0.052(4) 0.040(4) 0.045(4) 0.001(3) -0.024(4) -0.007(3) C20 0.040(3) 0.028(3) 0.047(4) -0.004(3) -0.017(3) -0.005(3) C3 0.056(4) 0.046(4) 0.032(3) -0.009(3) -0.013(3) 0.013(4) C9 0.045(4) 0.027(3) 0.073(5) 0.013(3) -0.030(4) -0.008(3) C5 0.041(4) 0.056(5) 0.028(3) 0.003(3) 0.006(3) 0.015(3) C10 0.055(5) 0.050(5) 0.090(7) 0.035(5) -0.031(5) -0.027(4) C12 0.028(3) 0.075(7) 0.078(5) 0.031(5) -0.003(3) -0.007(3) C15 0.088(6) 0.030(4) 0.069(6) 0.002(4) -0.038(5) -0.001(4) C16 0.027(3) 0.053(5) 0.065(5) 0.013(4) 0.004(3) 0.007(3) C11 0.030(4) 0.079(7) 0.099(7) 0.049(6) -0.018(4) -0.020(4) _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 2.123(5) . ? Sb1 S1 2.2929(17) . ? Sb1 N1 2.416(4) . ? Sb1 N2 2.417(4) . ? N1 C7 1.279(7) . ? N1 C8 1.455(8) . ? C1 C2 1.395(8) . ? C1 C6 1.408(8) . ? C19 C18 1.385(9) . ? C19 C20 1.390(8) . ? C19 C25 1.492(8) . ? C18 C23 1.390(8) . ? C18 N2 1.445(7) . ? N2 C17 1.279(8) . ? C4 C5 1.392(10) . ? C4 C3 1.395(10) . ? C4 H4 0.9301 . ? C22 C23 1.376(8) . ? C22 C21 1.380(9) . ? C22 H22 0.9301 . ? C17 C6 1.493(9) . ? C17 C24 1.501(8) . ? C2 C3 1.391(8) . ? C2 C7 1.481(9) . ? C25 H25A 0.9600 . ? C25 H25B 0.9599 . ? C25 H25C 0.9601 . ? C23 C26 1.508(8) . ? C8 C9 1.396(10) . ? C8 C13 1.406(10) . ? C6 C5 1.387(9) . ? C7 C14 1.512(8) . ? C13 C12 1.398(9) . ? C13 C16 1.489(11) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9599 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9599 . ? C26 H26A 0.9599 . ? C26 H26B 0.9601 . ? C26 H26C 0.9599 . ? C21 C20 1.376(9) . ? C21 H21 0.9301 . ? C20 H20 0.9302 . ? C3 H3 0.9301 . ? C9 C10 1.416(11) . ? C9 C15 1.500(11) . ? C5 H5 0.9301 . ? C10 C11 1.380(14) . ? C10 H10 0.9301 . ? C12 C11 1.366(13) . ? C12 H12 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9601 . ? C16 H16B 0.9601 . ? C16 H16C 0.9600 . ? C11 H11 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 C1 Sb1 S1 106.11(16) . . ? C1 Sb1 N1 72.52(19) . . ? S1 Sb1 N1 97.78(12) . . ? C1 Sb1 N2 72.09(19) . . ? S1 Sb1 N2 94.06(12) . . ? N1 Sb1 N2 144.54(16) . . ? C7 N1 C8 124.0(5) . . ? C7 N1 Sb1 113.7(4) . . ? C8 N1 Sb1 120.8(4) . . ? C2 C1 C6 120.4(5) . . ? C2 C1 Sb1 119.4(4) . . ? C6 C1 Sb1 120.1(4) . . ? C18 C19 C20 117.5(6) . . ? C18 C19 C25 122.2(5) . . ? C20 C19 C25 120.3(6) . . ? C19 C18 C23 122.4(5) . . ? C19 C18 N2 119.6(5) . . ? C23 C18 N2 117.8(5) . . ? C17 N2 C18 123.9(5) . . ? C17 N2 Sb1 115.5(4) . . ? C18 N2 Sb1 120.6(3) . . ? C5 C4 C3 120.6(6) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.8 . . ? C23 C22 C21 120.2(6) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 120.1 . . ? N2 C17 C6 115.6(5) . . ? N2 C17 C24 124.5(5) . . ? C6 C17 C24 119.9(5) . . ? C3 C2 C1 119.2(6) . . ? C3 C2 C7 123.6(5) . . ? C1 C2 C7 117.1(5) . . ? C19 C25 H25A 109.2 . . ? C19 C25 H25B 109.3 . . ? H25A C25 H25B 109.5 . . ? C19 C25 H25C 109.9 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C23 C18 118.5(5) . . ? C22 C23 C26 120.1(5) . . ? C18 C23 C26 121.4(5) . . ? C9 C8 C13 122.6(7) . . ? C9 C8 N1 117.5(7) . . ? C13 C8 N1 119.7(6) . . ? C5 C6 C1 119.8(6) . . ? C5 C6 C17 123.3(6) . . ? C1 C6 C17 116.8(5) . . ? N1 C7 C2 116.7(5) . . ? N1 C7 C14 123.0(6) . . ? C2 C7 C14 120.4(5) . . ? C12 C13 C8 116.7(7) . . ? C12 C13 C16 121.8(7) . . ? C8 C13 C16 121.5(6) . . ? C17 C24 H24A 109.2 . . ? C17 C24 H24B 109.9 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.4 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C7 C14 H14A 109.2 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.7 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.4 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C20 C21 C22 120.6(6) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.8 . . ? C21 C20 C19 120.8(6) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.4 . . ? C2 C3 C4 120.3(6) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 119.3 . . ? C8 C9 C10 117.3(8) . . ? C8 C9 C15 120.7(7) . . ? C10 C9 C15 122.0(7) . . ? C6 C5 C4 119.6(7) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.3 . . ? C11 C10 C9 121.0(8) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.3 . . ? C11 C12 C13 122.6(9) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.8 . . ? C9 C15 H15A 109.4 . . ? C9 C15 H15B 109.7 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.3 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.3 . . ? C13 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.8 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C11 C10 119.8(8) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 119.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.368 _refine_diff_density_min -1.007 _refine_diff_density_rms 0.117