# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ji Hoon Park' _publ_contact_author_email penny99@snu.ac.kr loop_ _publ_author_name 'Youjung Park' 'Sun Young Kim' 'Ji Hoon Park' 'Young Keun Chung' data_yj5 _database_code_depnum_ccdc_archive 'CCDC 804791' #TrackingRef 'yj5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common gold-yj _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N O3 S' _chemical_formula_sum 'C20 H21 N O3 S' _chemical_formula_weight 355.44 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.8824(4) _cell_length_b 13.2869(7) _cell_length_c 17.5082(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.799(3) _cell_angle_gamma 90.00 _cell_volume 1812.10(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7365 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4130 _reflns_number_gt 2451 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP32 _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0642P)^2^+0.0577P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4130 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 H14 H -0.550(3) 0.4347(16) 0.3029(13) 0.061(7) Uiso 1 1 d . . . H13A H -0.544(4) 0.503(2) 0.1835(16) 0.084(8) Uiso 1 1 d . . . H1A H -0.468(5) 0.316(3) -0.113(2) 0.121(15) Uiso 1 1 d . . . H7 H -0.303(4) 0.477(2) -0.0415(19) 0.099(10) Uiso 1 1 d . . . H16 H -0.498(4) 0.647(2) 0.3577(17) 0.095(11) Uiso 1 1 d . . . H1B H -0.395(4) 0.223(3) -0.092(2) 0.124(15) Uiso 1 1 d . . . H9 H -0.316(3) 0.3478(17) 0.3763(12) 0.057(6) Uiso 1 1 d . . . H12A H -0.182(3) 0.685(2) 0.3020(15) 0.081(8) Uiso 1 1 d . . . H1C H -0.300(5) 0.300(3) -0.139(2) 0.151(16) Uiso 1 1 d . . . H12B H -0.048(3) 0.656(2) 0.2535(16) 0.080(8) Uiso 1 1 d . . . H3 H -0.208(3) 0.189(2) 0.0279(15) 0.083(8) Uiso 1 1 d . . . H6 H -0.139(3) 0.5297(19) 0.0706(14) 0.066(7) Uiso 1 1 d . . . H18 H -0.380(4) 0.696(3) 0.584(2) 0.125(12) Uiso 1 1 d . . . H12C H -0.014(3) 0.6248(18) 0.3419(16) 0.071(8) Uiso 1 1 d . . . H20 H -0.161(4) 0.474(2) 0.4810(17) 0.094(11) Uiso 1 1 d . . . H17 H -0.525(5) 0.739(3) 0.463(2) 0.136(14) Uiso 1 1 d . . . H4 H -0.039(3) 0.2509(17) 0.1370(12) 0.054(7) Uiso 1 1 d . . . H19 H -0.199(4) 0.555(2) 0.594(2) 0.104(12) Uiso 1 1 d . . . H8A H -0.054(3) 0.3195(19) 0.3278(14) 0.074(8) Uiso 1 1 d . . . H13B H -0.404(3) 0.410(2) 0.1747(16) 0.085(9) Uiso 1 1 d . . . H8B H -0.187(3) 0.3081(18) 0.2471(14) 0.072(8) Uiso 1 1 d . . . S1 S 0.04849(7) 0.43889(5) 0.20166(3) 0.0511(2) Uani 1 1 d . . . N1 N -0.0743(2) 0.44871(12) 0.26871(10) 0.0423(4) Uani 1 1 d . . . O1 O -0.30966(19) 0.54761(11) 0.20611(9) 0.0551(4) Uani 1 1 d . . . C11 C -0.1917(3) 0.53563(15) 0.27574(12) 0.0432(5) Uani 1 1 d . . . C15 C -0.3200(3) 0.55456(17) 0.40758(13) 0.0507(6) Uani 1 1 d . . . O2 O 0.1111(2) 0.53694(12) 0.18749(10) 0.0662(5) Uani 1 1 d . . . O3 O 0.16799(18) 0.36022(13) 0.22788(10) 0.0679(5) Uani 1 1 d . . . C10 C -0.2997(2) 0.49721(16) 0.33665(12) 0.0442(5) Uani 1 1 d . . . C9 C -0.2926(3) 0.38464(17) 0.33213(14) 0.0507(6) Uani 1 1 d . . . C14 C -0.4409(3) 0.44113(18) 0.28725(14) 0.0548(6) Uani 1 1 d . . . C5 C -0.0758(3) 0.39516(17) 0.11579(12) 0.0479(5) Uani 1 1 d . . . C8 C -0.1453(3) 0.35265(17) 0.29307(17) 0.0555(6) Uani 1 1 d . . . C13 C -0.4369(3) 0.4696(2) 0.20438(16) 0.0638(7) Uani 1 1 d . . . C12 C -0.0986(4) 0.63332(19) 0.29432(19) 0.0608(7) Uani 1 1 d . . . C4 C -0.0927(3) 0.2934(2) 0.10143(17) 0.0627(7) Uani 1 1 d . . . C2 C -0.2691(3) 0.3259(2) -0.02120(14) 0.0621(7) Uani 1 1 d . . . C7 C -0.2509(4) 0.4269(2) -0.00579(16) 0.0704(7) Uani 1 1 d . . . C20 C -0.2331(4) 0.5266(3) 0.47858(16) 0.0693(8) Uani 1 1 d . . . C6 C -0.1561(4) 0.4620(2) 0.06171(15) 0.0640(7) Uani 1 1 d . . . C3 C -0.1896(4) 0.2598(2) 0.03388(17) 0.0703(7) Uani 1 1 d . . . C16 C -0.4299(4) 0.6355(2) 0.4046(2) 0.0827(9) Uani 1 1 d . . . C1 C -0.3680(6) 0.2877(4) -0.0964(2) 0.0899(11) Uani 1 1 d . . . C19 C -0.2514(5) 0.5783(4) 0.5444(2) 0.0921(11) Uani 1 1 d . . . C17 C -0.4475(6) 0.6879(3) 0.4718(3) 0.1076(13) Uani 1 1 d . . . C18 C -0.3579(6) 0.6579(3) 0.5409(3) 0.1038(15) 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 0.0404(3) 0.0573(4) 0.0561(4) -0.0036(3) 0.0091(2) -0.0038(3) N1 0.0419(9) 0.0391(10) 0.0463(10) 0.0029(8) 0.0076(8) -0.0022(7) O1 0.0539(9) 0.0608(10) 0.0481(9) 0.0110(7) -0.0004(7) 0.0021(8) C11 0.0478(12) 0.0408(12) 0.0403(12) 0.0039(9) 0.0048(9) -0.0001(9) C15 0.0531(13) 0.0499(14) 0.0518(14) -0.0015(11) 0.0170(11) -0.0054(11) O2 0.0643(10) 0.0659(11) 0.0727(12) -0.0074(9) 0.0244(9) -0.0244(9) O3 0.0445(8) 0.0746(12) 0.0822(12) -0.0060(9) 0.0026(8) 0.0142(8) C10 0.0433(11) 0.0458(12) 0.0433(12) -0.0005(10) 0.0062(9) 0.0000(10) C9 0.0561(13) 0.0455(13) 0.0521(14) 0.0036(11) 0.0129(11) -0.0071(11) C14 0.0427(12) 0.0659(16) 0.0555(15) -0.0011(12) 0.0065(11) -0.0072(11) C5 0.0484(12) 0.0518(14) 0.0454(13) -0.0020(10) 0.0131(10) 0.0010(10) C8 0.0635(15) 0.0395(13) 0.0661(17) 0.0047(12) 0.0181(13) -0.0008(11) C13 0.0534(15) 0.080(2) 0.0545(16) 0.0015(14) -0.0037(12) -0.0086(14) C12 0.0765(18) 0.0434(14) 0.0653(18) -0.0029(13) 0.0196(16) -0.0126(14) C4 0.0701(16) 0.0517(17) 0.0644(18) -0.0010(13) 0.0041(13) 0.0076(13) C2 0.0672(15) 0.0670(17) 0.0522(15) -0.0045(13) 0.0097(12) -0.0131(13) C7 0.094(2) 0.0651(19) 0.0493(16) 0.0040(14) 0.0017(14) -0.0019(15) C20 0.0637(16) 0.090(2) 0.0542(17) -0.0103(15) 0.0077(13) -0.0042(16) C6 0.0928(19) 0.0463(15) 0.0529(16) 0.0023(12) 0.0116(14) -0.0072(14) C3 0.0873(18) 0.0514(17) 0.0703(19) -0.0117(14) 0.0060(15) -0.0030(15) C16 0.104(2) 0.068(2) 0.082(2) 0.0005(17) 0.034(2) 0.0222(18) C1 0.104(3) 0.095(3) 0.064(2) -0.0091(19) -0.007(2) -0.020(2) C19 0.101(2) 0.120(3) 0.058(2) -0.027(2) 0.0203(18) -0.031(2) C17 0.147(3) 0.066(2) 0.127(4) -0.008(2) 0.079(3) 0.013(2) C18 0.143(3) 0.093(3) 0.093(3) -0.045(3) 0.075(3) -0.060(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4282(16) . ? S1 O3 1.4348(16) . ? S1 N1 1.6371(17) . ? S1 C5 1.763(2) . ? N1 C8 1.482(3) . ? N1 C11 1.497(2) . ? O1 C11 1.425(2) . ? O1 C13 1.439(3) . ? C11 C12 1.502(3) . ? C11 C10 1.549(3) . ? C15 C20 1.376(3) . ? C15 C16 1.377(4) . ? C15 C10 1.486(3) . ? C10 C14 1.499(3) . ? C10 C9 1.499(3) . ? C9 C8 1.496(3) . ? C9 C14 1.505(3) . ? C14 C13 1.505(4) . ? C5 C4 1.377(3) . ? C5 C6 1.379(3) . ? C4 C3 1.380(4) . ? C2 C7 1.372(4) . ? C2 C3 1.382(4) . ? C2 C1 1.512(4) . ? C7 C6 1.379(4) . ? C20 C19 1.369(4) . ? C16 C17 1.393(5) . ? C19 C18 1.346(5) . ? C17 C18 1.364(6) . ? 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 O3 119.53(10) . . ? O2 S1 N1 108.05(9) . . ? O3 S1 N1 105.06(9) . . ? O2 S1 C5 108.32(11) . . ? O3 S1 C5 106.54(10) . . ? N1 S1 C5 109.00(9) . . ? C8 N1 C11 112.05(16) . . ? C8 N1 S1 115.37(14) . . ? C11 N1 S1 124.14(13) . . ? C11 O1 C13 107.41(16) . . ? O1 C11 N1 110.28(16) . . ? O1 C11 C12 108.79(19) . . ? N1 C11 C12 113.40(19) . . ? O1 C11 C10 105.68(15) . . ? N1 C11 C10 102.36(15) . . ? C12 C11 C10 115.94(19) . . ? C20 C15 C16 118.0(3) . . ? C20 C15 C10 120.9(2) . . ? C16 C15 C10 121.1(2) . . ? C15 C10 C14 124.86(18) . . ? C15 C10 C9 124.41(19) . . ? C14 C10 C9 60.27(15) . . ? C15 C10 C11 123.15(17) . . ? C14 C10 C11 101.79(17) . . ? C9 C10 C11 105.28(17) . . ? C8 C9 C10 110.20(19) . . ? C8 C9 C14 119.8(2) . . ? C10 C9 C14 59.86(15) . . ? C10 C14 C13 107.9(2) . . ? C10 C14 C9 59.87(14) . . ? C13 C14 C9 120.0(2) . . ? C4 C5 C6 119.0(2) . . ? C4 C5 S1 120.32(19) . . ? C6 C5 S1 120.68(19) . . ? N1 C8 C9 103.91(18) . . ? O1 C13 C14 106.2(2) . . ? C5 C4 C3 120.0(3) . . ? C7 C2 C3 117.5(3) . . ? C7 C2 C1 121.6(3) . . ? C3 C2 C1 120.8(3) . . ? C2 C7 C6 121.7(3) . . ? C19 C20 C15 121.5(4) . . ? C7 C6 C5 120.2(3) . . ? C4 C3 C2 121.6(3) . . ? C15 C16 C17 120.1(4) . . ? C18 C19 C20 120.1(4) . . ? C18 C17 C16 120.0(4) . . ? C19 C18 C17 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.178 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042