# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a20511c _database_code_depnum_ccdc_archive 'CCDC 892027' #TrackingRef '- a20511c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H31 N O2 S' _chemical_formula_weight 481.63 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' O O 0.0106 0.0060 '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' N N 0.0061 0.0033 '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 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 10.517(4) _cell_length_b 13.401(5) _cell_length_c 18.699(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.737(5) _cell_angle_gamma 90.00 _cell_volume 2635.2(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 977 _cell_measurement_theta_min 2.1785 _cell_measurement_theta_max 27.7795 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9778 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 10715 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4631 _reflns_number_gt 3212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1016P)^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 SHELXL _refine_ls_extinction_coef 0.0035(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4631 _refine_ls_number_parameters 323 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.021 _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 S1 S 0.57341(5) 0.75162(4) 0.20304(3) 0.0519(2) Uani 1 1 d . . . O1 O 0.60247(16) 0.76081(13) 0.27755(9) 0.0686(5) Uani 1 1 d . . . O2 O 0.60434(14) 0.83135(11) 0.15634(10) 0.0616(5) Uani 1 1 d . . . N1 N 0.41839(16) 0.73108(14) 0.19681(10) 0.0488(5) Uani 1 1 d . . . C1 C 0.3621(2) 0.6774(2) 0.25761(14) 0.0673(7) Uani 1 1 d . . . H1A H 0.2735 0.6655 0.2479 0.101 Uiso 1 1 calc R . . H1B H 0.3710 0.7170 0.3002 0.101 Uiso 1 1 calc R . . H1C H 0.4051 0.6148 0.2643 0.101 Uiso 1 1 calc R . . C2 C 0.3534(2) 0.73449(15) 0.13018(12) 0.0463(5) Uani 1 1 d . . . C3 C 0.2161(2) 0.75607(16) 0.13805(12) 0.0487(5) Uani 1 1 d . . . C4 C 0.1748(2) 0.83779(19) 0.17705(15) 0.0655(7) Uani 1 1 d . . . H4 H 0.2338 0.8808 0.1980 0.079 Uiso 1 1 calc R . . C5 C 0.0459(3) 0.8555(2) 0.18484(17) 0.0816(9) Uani 1 1 d . . . H5 H 0.0187 0.9113 0.2100 0.098 Uiso 1 1 calc R . . C6 C -0.0412(3) 0.7915(3) 0.15576(17) 0.0832(9) Uani 1 1 d . . . H6 H -0.1276 0.8039 0.1610 0.100 Uiso 1 1 calc R . . C7 C -0.0024(2) 0.7095(2) 0.11901(15) 0.0723(8) Uani 1 1 d . . . H7 H -0.0624 0.6652 0.1004 0.087 Uiso 1 1 calc R . . C8 C 0.1257(2) 0.69166(19) 0.10923(13) 0.0585(6) Uani 1 1 d . . . H8 H 0.1514 0.6362 0.0832 0.070 Uiso 1 1 calc R . . C9 C 0.41118(19) 0.72228(15) 0.06601(12) 0.0436(5) Uani 1 1 d . . . C10 C 0.3646(2) 0.76080(15) -0.00369(12) 0.0477(5) Uani 1 1 d . . . C11 C 0.2547(2) 0.83127(19) -0.01657(15) 0.0643(7) Uani 1 1 d . A . H11A H 0.1824 0.8090 0.0110 0.077 Uiso 1 1 calc R . . H11B H 0.2304 0.8290 -0.0668 0.077 Uiso 1 1 calc R . . C12 C 0.2860(3) 0.9384(2) 0.0038(2) 0.1011(11) Uani 1 1 d DU . . H12A H 0.3463 0.9638 -0.0305 0.121 Uiso 0.492(16) 1 calc PR A 1 H12B H 0.3289 0.9374 0.0501 0.121 Uiso 0.492(16) 1 calc PR A 1 H12C H 0.2836 0.9461 0.0554 0.121 Uiso 0.508(16) 1 calc PR A 2 H12D H 0.3709 0.9553 -0.0119 0.121 Uiso 0.508(16) 1 calc PR A 2 C13 C 0.1756(9) 1.0132(7) 0.0081(10) 0.131(6) Uani 0.492(16) 1 d PDU A 1 H13A H 0.2080 1.0774 0.0219 0.197 Uiso 0.492(16) 1 calc PR A 1 H13B H 0.1157 0.9907 0.0429 0.197 Uiso 0.492(16) 1 calc PR A 1 H13C H 0.1342 1.0181 -0.0378 0.197 Uiso 0.492(16) 1 calc PR A 1 C13' C 0.18904(16) 1.00756(12) -0.03143(9) 0.160(6) Uani 0.508(16) 1 d PDU A 2 H13D H 0.2081 1.0754 -0.0188 0.240 Uiso 0.508(16) 1 calc PR A 2 H13E H 0.1054 0.9908 -0.0153 0.240 Uiso 0.508(16) 1 calc PR A 2 H13F H 0.1924 1.0000 -0.0824 0.240 Uiso 0.508(16) 1 calc PR A 2 C15 C 0.45348(16) 0.74002(12) -0.05341(9) 0.0478(5) Uani 1 1 d R . . C16 C 0.45863(16) 0.77756(12) -0.12827(9) 0.0632(7) Uani 1 1 d R . . H16A H 0.3738 0.7959 -0.1445 0.076 Uiso 1 1 calc R . . H16B H 0.4896 0.7252 -0.1593 0.076 Uiso 1 1 calc R . . C17 C 0.5489(3) 0.8708(3) -0.13264(18) 0.1031(11) Uani 1 1 d . . . H17A H 0.5302 0.9150 -0.0931 0.124 Uiso 1 1 calc R . . H17B H 0.6360 0.8483 -0.1266 0.124 Uiso 1 1 calc R . . C18 C 0.5393(4) 0.9271(3) -0.1983(2) 0.1042(11) Uani 1 1 d . . . H18A H 0.5505 0.8831 -0.2383 0.156 Uiso 1 1 calc R . . H18B H 0.6040 0.9776 -0.1987 0.156 Uiso 1 1 calc R . . H18C H 0.4571 0.9579 -0.2017 0.156 Uiso 1 1 calc R . . C19 C 0.5577(2) 0.68367(15) -0.01943(12) 0.0461(5) Uani 1 1 d . . . C20 C 0.6732(2) 0.65024(16) -0.05748(12) 0.0470(5) Uani 1 1 d . . . C21 C 0.6670(2) 0.58441(17) -0.11503(12) 0.0572(6) Uani 1 1 d . . . H21 H 0.5885 0.5604 -0.1307 0.069 Uiso 1 1 calc R . . C22 C 0.7756(3) 0.55465(19) -0.14890(14) 0.0677(7) Uani 1 1 d . . . H22 H 0.7700 0.5097 -0.1867 0.081 Uiso 1 1 calc R . . C23 C 0.8917(3) 0.5901(2) -0.12785(15) 0.0716(8) Uani 1 1 d . . . H23 H 0.9647 0.5701 -0.1514 0.086 Uiso 1 1 calc R . . C24 C 0.8999(2) 0.6553(2) -0.07192(16) 0.0710(7) Uani 1 1 d . . . H24 H 0.9789 0.6796 -0.0572 0.085 Uiso 1 1 calc R . . C25 C 0.7915(2) 0.68533(18) -0.03698(13) 0.0584(6) Uani 1 1 d . . . H25 H 0.7984 0.7299 0.0010 0.070 Uiso 1 1 calc R . . C26 C 0.53489(19) 0.67355(15) 0.05131(12) 0.0441(5) Uani 1 1 d . . . C27 C 0.61025(18) 0.61112(15) 0.10154(11) 0.0432(5) Uani 1 1 d . . . C28 C 0.6585(2) 0.51873(15) 0.07971(12) 0.0501(5) Uani 1 1 d . . . H28 H 0.6439 0.4971 0.0331 0.060 Uiso 1 1 calc R . . C29 C 0.7273(2) 0.45942(17) 0.12632(14) 0.0583(6) Uani 1 1 d . . . H29 H 0.7591 0.3987 0.1104 0.070 Uiso 1 1 calc R . . C30 C 0.7500(2) 0.48818(19) 0.19568(14) 0.0648(7) Uani 1 1 d . . . H30 H 0.7967 0.4474 0.2265 0.078 Uiso 1 1 calc R . . C31 C 0.7028(2) 0.57840(18) 0.21952(13) 0.0581(6) Uani 1 1 d . . . H31 H 0.7155 0.5982 0.2667 0.070 Uiso 1 1 calc R . . C32 C 0.63624(19) 0.63868(16) 0.17204(12) 0.0465(5) 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 S1 0.0355(3) 0.0550(4) 0.0651(4) -0.0137(3) -0.0030(3) -0.0004(2) O1 0.0510(11) 0.0864(12) 0.0681(11) -0.0286(9) -0.0112(8) 0.0025(8) O2 0.0446(9) 0.0504(9) 0.0897(12) -0.0083(8) 0.0045(8) -0.0040(7) N1 0.0327(10) 0.0598(11) 0.0539(11) -0.0087(9) -0.0002(8) 0.0014(8) C1 0.0560(16) 0.0837(18) 0.0622(16) 0.0009(13) 0.0007(12) -0.0104(13) C2 0.0354(12) 0.0441(12) 0.0592(14) -0.0028(10) -0.0006(10) -0.0014(9) C3 0.0346(12) 0.0573(13) 0.0542(13) 0.0018(10) 0.0049(10) 0.0032(10) C4 0.0479(15) 0.0695(16) 0.0793(18) -0.0124(13) 0.0060(13) 0.0056(12) C5 0.0510(16) 0.094(2) 0.101(2) -0.0035(17) 0.0192(15) 0.0217(16) C6 0.0373(15) 0.116(3) 0.096(2) 0.029(2) 0.0085(15) 0.0125(17) C7 0.0389(14) 0.098(2) 0.0798(19) 0.0240(17) -0.0093(13) -0.0115(14) C8 0.0455(14) 0.0670(15) 0.0629(15) 0.0080(12) -0.0075(11) -0.0076(11) C9 0.0333(11) 0.0433(11) 0.0542(13) -0.0015(9) 0.0016(10) 0.0008(9) C10 0.0376(12) 0.0463(12) 0.0590(14) 0.0023(10) -0.0026(11) 0.0009(9) C11 0.0480(15) 0.0724(17) 0.0727(17) 0.0159(13) 0.0027(12) 0.0124(12) C12 0.087(2) 0.0615(18) 0.155(3) 0.0152(19) 0.014(2) 0.0208(16) C13 0.125(8) 0.084(6) 0.183(15) 0.003(5) -0.017(6) 0.047(5) C13' 0.200(11) 0.106(7) 0.175(12) 0.020(7) 0.022(8) 0.090(7) C15 0.0432(13) 0.0466(12) 0.0534(13) 0.0029(10) -0.0019(11) -0.0022(9) C16 0.0553(15) 0.0725(16) 0.0617(15) 0.0114(13) 0.0040(12) 0.0045(13) C17 0.101(3) 0.128(3) 0.081(2) 0.032(2) 0.0240(18) -0.014(2) C18 0.094(3) 0.101(2) 0.118(3) 0.028(2) 0.009(2) 0.002(2) C19 0.0398(12) 0.0447(12) 0.0538(14) -0.0032(10) 0.0011(10) -0.0002(9) C20 0.0437(13) 0.0471(12) 0.0502(12) 0.0029(10) 0.0051(10) 0.0014(10) C21 0.0540(15) 0.0596(14) 0.0584(14) -0.0043(11) 0.0085(11) -0.0026(11) C22 0.079(2) 0.0608(15) 0.0635(16) -0.0047(12) 0.0207(14) 0.0082(14) C23 0.0550(17) 0.0823(19) 0.0780(19) 0.0067(15) 0.0259(14) 0.0115(14) C24 0.0415(14) 0.0867(19) 0.0851(19) 0.0037(16) 0.0063(13) -0.0010(13) C25 0.0480(14) 0.0633(15) 0.0640(15) -0.0049(11) 0.0007(12) -0.0013(11) C26 0.0358(12) 0.0429(11) 0.0537(13) -0.0042(9) 0.0003(10) 0.0000(9) C27 0.0305(11) 0.0442(11) 0.0551(13) 0.0003(9) 0.0029(9) -0.0017(9) C28 0.0408(12) 0.0454(12) 0.0641(14) -0.0040(11) 0.0042(10) 0.0015(10) C29 0.0472(14) 0.0443(12) 0.0834(18) 0.0021(12) 0.0021(13) 0.0058(10) C30 0.0525(15) 0.0631(15) 0.0786(18) 0.0096(13) -0.0106(13) 0.0091(12) C31 0.0470(14) 0.0670(15) 0.0600(14) -0.0009(12) -0.0095(11) 0.0052(12) C32 0.0309(11) 0.0511(12) 0.0575(13) -0.0041(10) -0.0018(10) -0.0002(9) _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 S1 O2 1.4203(18) . ? S1 O1 1.4280(18) . ? S1 N1 1.6560(19) . ? S1 C32 1.753(2) . ? N1 C2 1.414(3) . ? N1 C1 1.476(3) . ? C2 C9 1.362(3) . ? C2 C3 1.482(3) . ? C3 C4 1.389(3) . ? C3 C8 1.388(3) . ? C4 C5 1.386(4) . ? C5 C6 1.363(4) . ? C6 C7 1.362(4) . ? C7 C8 1.383(3) . ? C9 C10 1.479(3) . ? C9 C26 1.485(3) . ? C10 C15 1.356(3) . ? C10 C11 1.510(3) . ? C11 C12 1.521(4) . ? C12 C13' 1.522(3) . ? C12 C13 1.536(7) . ? C15 C19 1.469(3) . ? C15 C16 1.4891 . ? C16 C17 1.572(4) . ? C17 C18 1.444(4) . ? C19 C26 1.354(3) . ? C19 C20 1.485(3) . ? C20 C25 1.380(3) . ? C20 C21 1.392(3) . ? C21 C22 1.372(3) . ? C22 C23 1.364(4) . ? C23 C24 1.364(4) . ? C24 C25 1.381(4) . ? C26 C27 1.480(3) . ? C27 C32 1.393(3) . ? C27 C28 1.401(3) . ? C28 C29 1.378(3) . ? C29 C30 1.371(3) . ? C30 C31 1.383(3) . ? C31 C32 1.384(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 O2 S1 O1 119.15(11) . . ? O2 S1 N1 108.35(10) . . ? O1 S1 N1 106.33(10) . . ? O2 S1 C32 110.85(11) . . ? O1 S1 C32 108.68(11) . . ? N1 S1 C32 102.02(10) . . ? C2 N1 C1 120.02(18) . . ? C2 N1 S1 121.39(16) . . ? C1 N1 S1 115.55(15) . . ? C9 C2 N1 123.81(19) . . ? C9 C2 C3 123.88(19) . . ? N1 C2 C3 112.29(19) . . ? C4 C3 C8 118.5(2) . . ? C4 C3 C2 121.2(2) . . ? C8 C3 C2 120.2(2) . . ? C5 C4 C3 120.2(3) . . ? C6 C5 C4 120.2(3) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 120.3(3) . . ? C7 C8 C3 120.3(3) . . ? C2 C9 C10 126.01(19) . . ? C2 C9 C26 128.18(19) . . ? C10 C9 C26 105.74(18) . . ? C15 C10 C9 108.01(18) . . ? C15 C10 C11 123.5(2) . . ? C9 C10 C11 127.1(2) . . ? C10 C11 C12 112.8(2) . . ? C13' C12 C11 108.9(3) . . ? C13' C12 C13 28.7(7) . . ? C11 C12 C13 117.8(5) . . ? C10 C15 C19 109.03(17) . . ? C10 C15 C16 127.52(11) . . ? C19 C15 C16 122.98(11) . . ? C15 C16 C17 110.29(14) . . ? C18 C17 C16 115.1(3) . . ? C26 C19 C15 109.49(18) . . ? C26 C19 C20 126.4(2) . . ? C15 C19 C20 123.94(19) . . ? C25 C20 C21 117.6(2) . . ? C25 C20 C19 120.3(2) . . ? C21 C20 C19 122.1(2) . . ? C22 C21 C20 120.7(2) . . ? C23 C22 C21 120.8(3) . . ? C24 C23 C22 119.5(2) . . ? C23 C24 C25 120.3(3) . . ? C24 C25 C20 121.1(2) . . ? C19 C26 C27 125.20(19) . . ? C19 C26 C9 107.66(18) . . ? C27 C26 C9 126.47(19) . . ? C32 C27 C28 116.28(19) . . ? C32 C27 C26 123.21(19) . . ? C28 C27 C26 120.50(19) . . ? C29 C28 C27 121.0(2) . . ? C30 C29 C28 121.3(2) . . ? C29 C30 C31 119.5(2) . . ? C30 C31 C32 119.0(2) . . ? C31 C32 C27 123.0(2) . . ? C31 C32 S1 118.78(18) . . ? C27 C32 S1 118.14(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.296 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.041