Supplementary Material (ESI) for Analyst This journal is (C) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mengqw@dlut.edu.cn _publ_contact_author_name 'Meng, Wei' _publ_author_name 'Wei Meng' data_p _database_code_depnum_ccdc_archive 'CCDC 809364' #TrackingRef '- CheckCIF.cif' _audit_update_record ; 2011-01-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O S' _chemical_formula_sum 'C12 H10 N2 O S' _chemical_formula_weight 230.28 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/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 20.459(11) _cell_length_b 9.635(5) _cell_length_c 23.657(12) _cell_angle_alpha 90.00 _cell_angle_beta 111.067(6) _cell_angle_gamma 90.00 _cell_volume 4352(4) _cell_formula_units_Z 16 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.71 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.275 _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 298(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 'Bruker SMART APEX CCD' _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 23289 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.39 _reflns_number_total 9592 _reflns_number_gt 5305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (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^)+(0.1064P)^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 9592 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1982 _refine_ls_wR_factor_gt 0.1616 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 S1 S 0.59800(5) 0.56901(8) 0.22074(3) 0.0528(2) Uani 1 1 d . . . S4 S 0.44895(4) 0.29818(9) 0.29682(3) 0.0436(2) Uani 1 1 d . . . O1 O 0.52039(10) 0.2539(2) 0.08870(8) 0.0477(5) Uani 1 1 d . . . O4 O 0.47929(10) 0.4863(2) 0.41627(8) 0.0448(5) Uani 1 1 d . . . N3 N 0.60523(12) 0.4277(2) 0.12298(9) 0.0369(5) Uani 1 1 d . . . N1 N 0.56367(12) 0.3778(2) 0.02535(9) 0.0392(6) Uani 1 1 d . . . H1A H 0.5401 0.3403 -0.0089 0.047 Uiso 1 1 calc R . . N11 N 0.43782(11) 0.3651(2) 0.48167(9) 0.0361(6) Uani 1 1 d . . . H11A H 0.4634 0.4008 0.5158 0.043 Uiso 1 1 calc R . . N10 N 0.39151(11) 0.3181(2) 0.38404(9) 0.0340(5) Uani 1 1 d . . . C12 C 0.63923(14) 0.5155(3) 0.09473(11) 0.0345(6) Uani 1 1 d . . . C13 C 0.55805(14) 0.3429(3) 0.07914(11) 0.0368(7) Uani 1 1 d . . . C16 C 0.38749(13) 0.2631(3) 0.47471(11) 0.0320(6) Uani 1 1 d . . . C17 C 0.37998(13) 0.3196(3) 0.32203(11) 0.0331(6) Uani 1 1 d . . . C18 C 0.44090(14) 0.4005(3) 0.42695(11) 0.0356(7) Uani 1 1 d . . . C21 C 0.61257(14) 0.4822(3) 0.03353(12) 0.0347(6) Uani 1 1 d . . . C22 C 0.35765(13) 0.2324(3) 0.41323(11) 0.0321(6) Uani 1 1 d . . . C25 C 0.61318(14) 0.4240(3) 0.18450(11) 0.0378(7) Uani 1 1 d . . . C27 C 0.31809(14) 0.3317(3) 0.27535(11) 0.0422(7) Uani 1 1 d . . . H27A H 0.2752 0.3443 0.2799 0.051 Uiso 1 1 calc R . . C29 C 0.30596(14) 0.1340(3) 0.39174(12) 0.0391(7) Uani 1 1 d . . . H29A H 0.2857 0.1144 0.3506 0.047 Uiso 1 1 calc R . . C31 C 0.31513(15) 0.0941(3) 0.49538(13) 0.0436(7) Uani 1 1 d . . . H31A H 0.3006 0.0452 0.5226 0.052 Uiso 1 1 calc R . . C32 C 0.63612(15) 0.5493(3) -0.00759(13) 0.0441(7) Uani 1 1 d . . . H32A H 0.6185 0.5271 -0.0486 0.053 Uiso 1 1 calc R . . C33 C 0.62711(14) 0.3131(3) 0.22200(11) 0.0404(6) Uani 1 1 d . . . H33A H 0.6364 0.2251 0.2106 0.049 Uiso 1 1 calc R . . C35 C 0.28516(15) 0.0649(3) 0.43416(13) 0.0430(7) Uani 1 1 d . . . H35A H 0.2503 -0.0024 0.4211 0.052 Uiso 1 1 calc R . . C38 C 0.71329(15) 0.6840(3) 0.07590(14) 0.0467(7) Uani 1 1 d . . . H38A H 0.7475 0.7523 0.0896 0.056 Uiso 1 1 calc R . . C39 C 0.61173(15) 0.4774(3) 0.28664(12) 0.0455(7) Uani 1 1 d . . . C42 C 0.68964(14) 0.6171(3) 0.11717(12) 0.0414(7) Uani 1 1 d . . . H42A H 0.7071 0.6399 0.1581 0.050 Uiso 1 1 calc R . . C46 C 0.36665(15) 0.1953(3) 0.51688(12) 0.0406(7) Uani 1 1 d . . . H46A H 0.3863 0.2164 0.5579 0.049 Uiso 1 1 calc R . . C47 C 0.39350(17) 0.3060(3) 0.22224(12) 0.0468(8) Uani 1 1 d . . . C50 C 0.62630(16) 0.3428(3) 0.27891(13) 0.0508(8) Uani 1 1 d . . . H50A H 0.6350 0.2763 0.3092 0.061 Uiso 1 1 calc R . . C53 C 0.68700(16) 0.6509(3) 0.01517(14) 0.0482(8) Uani 1 1 d . . . H53A H 0.7037 0.6978 -0.0112 0.058 Uiso 1 1 calc R . . C55 C 0.32684(16) 0.3230(3) 0.21891(12) 0.0497(8) Uani 1 1 d . . . H55A H 0.2894 0.3285 0.1822 0.060 Uiso 1 1 calc R . . C57 C 0.4223(2) 0.2909(4) 0.17202(14) 0.0700(11) Uani 1 1 d . . . H57A H 0.3846 0.2973 0.1335 0.105 Uiso 1 1 calc R . . H57B H 0.4449 0.2024 0.1754 0.105 Uiso 1 1 calc R . . H57C H 0.4556 0.3635 0.1753 0.105 Uiso 1 1 calc R . . S2 S 0.09460(4) 0.17875(8) 0.21701(3) 0.0502(2) Uani 1 1 d . . . S3 S -0.04842(4) 0.45151(9) 0.30116(3) 0.0430(2) Uani 1 1 d . . . O3 O -0.01924(10) 0.2651(2) 0.42126(8) 0.0446(5) Uani 1 1 d . . . O2 O 0.01819(11) 0.4941(2) 0.08419(8) 0.0480(5) Uani 1 1 d . . . N8 N -0.06287(12) 0.3862(2) 0.48542(9) 0.0390(6) Uani 1 1 d . . . H8A H -0.0379 0.3506 0.5198 0.047 Uiso 1 1 calc R . . N7 N -0.10726(11) 0.4322(2) 0.38763(9) 0.0352(5) Uani 1 1 d . . . N5 N 0.10318(12) 0.3207(2) 0.11982(9) 0.0382(6) Uani 1 1 d . . . N4 N 0.06361(12) 0.3702(2) 0.02244(9) 0.0388(6) Uani 1 1 d . . . H4A H 0.0403 0.4071 -0.0120 0.047 Uiso 1 1 calc R . . C15 C -0.05825(14) 0.3507(3) 0.43132(11) 0.0343(6) Uani 1 1 d . . . C19 C -0.14196(14) 0.5177(3) 0.41604(11) 0.0327(6) Uani 1 1 d . . . C20 C -0.11787(13) 0.4306(3) 0.32573(11) 0.0346(6) Uani 1 1 d . . . C23 C 0.05699(14) 0.4058(3) 0.07575(11) 0.0374(7) Uani 1 1 d . . . C24 C 0.13835(14) 0.2338(3) 0.09258(11) 0.0353(6) Uani 1 1 d . . . C26 C -0.11361(14) 0.4878(3) 0.47748(12) 0.0355(6) Uani 1 1 d . . . C28 C -0.17957(14) 0.4189(3) 0.27850(11) 0.0415(7) Uani 1 1 d . . . H28A H -0.2228 0.4067 0.2825 0.050 Uiso 1 1 calc R . . C30 C 0.12525(15) 0.4350(3) 0.21886(12) 0.0447(7) Uani 1 1 d . . . H30A H 0.1349 0.5230 0.2077 0.054 Uiso 1 1 calc R . . C34 C 0.11323(14) 0.2663(3) 0.03135(11) 0.0360(7) Uani 1 1 d . . . C36 C 0.11067(14) 0.3246(3) 0.18123(12) 0.0378(6) Uani 1 1 d . . . C37 C -0.19406(15) 0.6161(3) 0.39328(12) 0.0415(7) Uani 1 1 d . . . H37A H -0.2134 0.6356 0.3521 0.050 Uiso 1 1 calc R . . C40 C 0.10938(15) 0.2683(3) 0.28339(12) 0.0449(7) Uani 1 1 d . . . C41 C -0.13628(15) 0.5557(3) 0.51859(12) 0.0423(7) Uani 1 1 d . . . H41A H -0.1173 0.5357 0.5598 0.051 Uiso 1 1 calc R . . C43 C -0.10266(16) 0.4451(3) 0.22650(12) 0.0451(7) Uani 1 1 d . . . C44 C -0.18835(15) 0.6547(3) 0.49612(13) 0.0455(8) Uani 1 1 d . . . H44A H -0.2048 0.7016 0.5227 0.055 Uiso 1 1 calc R . . C45 C -0.21620(15) 0.6850(3) 0.43523(13) 0.0442(7) Uani 1 1 d . . . H45A H -0.2506 0.7530 0.4217 0.053 Uiso 1 1 calc R . . C48 C 0.13826(15) 0.2006(3) -0.00883(13) 0.0446(7) Uani 1 1 d . . . H48A H 0.1219 0.2236 -0.0497 0.054 Uiso 1 1 calc R . . C49 C 0.18866(14) 0.1329(3) 0.11603(12) 0.0419(7) Uani 1 1 d . . . H49A H 0.2051 0.1103 0.1570 0.050 Uiso 1 1 calc R . . C51 C 0.21384(15) 0.0659(3) 0.07538(14) 0.0485(8) Uani 1 1 d . . . H51A H 0.2481 -0.0021 0.0897 0.058 Uiso 1 1 calc R . . C52 C 0.12435(16) 0.4039(3) 0.27656(13) 0.0491(8) Uani 1 1 d . . . H52A H 0.1331 0.4695 0.3072 0.059 Uiso 1 1 calc R . . C54 C -0.16990(16) 0.4275(3) 0.22232(12) 0.0484(8) Uani 1 1 d . . . H54A H -0.2069 0.4215 0.1854 0.058 Uiso 1 1 calc R . . C56 C -0.0739(2) 0.4584(4) 0.17661(14) 0.0654(10) Uani 1 1 d . . . H56A H -0.1115 0.4531 0.1381 0.098 Uiso 1 1 calc R . . H56B H -0.0412 0.3846 0.1798 0.098 Uiso 1 1 calc R . . H56C H -0.0505 0.5461 0.1800 0.098 Uiso 1 1 calc R . . C58 C 0.18899(16) 0.0986(3) 0.01462(14) 0.0510(8) Uani 1 1 d . . . H58A H 0.2065 0.0516 -0.0112 0.061 Uiso 1 1 calc R . . C59 C 0.10396(17) 0.1976(4) 0.33751(12) 0.0603(9) Uani 1 1 d . . . H59A H 0.1133 0.2631 0.3700 0.090 Uiso 1 1 calc R . . H59B H 0.1375 0.1234 0.3497 0.090 Uiso 1 1 calc R . . H59C H 0.0576 0.1606 0.3277 0.090 Uiso 1 1 calc R . . C60 C 0.60674(18) 0.5469(4) 0.34102(13) 0.0659(10) Uani 1 1 d . . . H60A H 0.6155 0.4804 0.3731 0.099 Uiso 1 1 calc R . . H60B H 0.5607 0.5852 0.3313 0.099 Uiso 1 1 calc R . . H60C H 0.6408 0.6200 0.3537 0.099 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 S1 0.0753(6) 0.0385(5) 0.0417(4) -0.0038(3) 0.0175(4) 0.0026(4) S4 0.0377(4) 0.0529(5) 0.0398(4) 0.0014(3) 0.0133(3) 0.0023(3) O1 0.0468(13) 0.0555(14) 0.0377(11) -0.0082(9) 0.0115(9) -0.0198(11) O4 0.0398(12) 0.0523(14) 0.0367(11) -0.0036(9) 0.0067(9) -0.0187(10) N3 0.0386(14) 0.0385(14) 0.0295(11) -0.0042(10) 0.0073(10) -0.0063(11) N1 0.0398(14) 0.0457(15) 0.0274(11) -0.0059(10) 0.0065(10) -0.0057(12) N11 0.0338(13) 0.0401(14) 0.0281(11) -0.0060(10) 0.0036(9) -0.0073(11) N10 0.0316(13) 0.0364(13) 0.0298(11) -0.0049(10) 0.0058(9) -0.0094(11) C12 0.0320(15) 0.0299(16) 0.0373(15) -0.0010(11) 0.0076(11) 0.0047(12) C13 0.0312(16) 0.0417(18) 0.0337(14) -0.0069(12) 0.0072(11) -0.0050(13) C16 0.0261(14) 0.0334(16) 0.0324(13) 0.0004(11) 0.0056(10) 0.0018(12) C17 0.0301(15) 0.0336(15) 0.0312(13) -0.0003(11) 0.0057(11) -0.0016(12) C18 0.0306(16) 0.0399(18) 0.0307(14) -0.0037(12) 0.0040(11) -0.0003(13) C21 0.0293(15) 0.0324(16) 0.0387(15) 0.0004(11) 0.0076(11) 0.0044(12) C22 0.0270(14) 0.0343(16) 0.0336(13) -0.0004(11) 0.0091(11) 0.0017(12) C25 0.0345(16) 0.0413(17) 0.0323(14) -0.0063(12) 0.0056(11) -0.0049(13) C27 0.0294(15) 0.0499(18) 0.0374(15) -0.0002(13) -0.0001(11) -0.0044(13) C29 0.0342(16) 0.0413(18) 0.0374(15) -0.0065(12) 0.0074(12) -0.0049(13) C31 0.0451(19) 0.0404(18) 0.0493(17) 0.0074(14) 0.0218(14) 0.0039(15) C32 0.0438(18) 0.0486(19) 0.0393(16) 0.0034(14) 0.0142(13) 0.0022(15) C33 0.0455(17) 0.0324(16) 0.0366(15) 0.0023(12) 0.0065(12) -0.0017(13) C35 0.0359(17) 0.0400(18) 0.0521(18) -0.0031(14) 0.0147(13) -0.0074(14) C38 0.0383(18) 0.0377(18) 0.0616(19) 0.0007(15) 0.0148(14) -0.0008(15) C39 0.0417(17) 0.058(2) 0.0330(15) -0.0075(13) 0.0092(12) -0.0131(15) C42 0.0355(17) 0.0382(18) 0.0429(16) -0.0051(13) 0.0048(13) -0.0015(13) C46 0.0440(18) 0.0425(18) 0.0340(14) 0.0013(13) 0.0124(12) 0.0021(15) C47 0.067(2) 0.0388(18) 0.0340(15) -0.0003(13) 0.0175(14) -0.0049(16) C50 0.053(2) 0.049(2) 0.0424(17) 0.0071(14) 0.0069(14) -0.0057(16) C53 0.0440(19) 0.0439(19) 0.0581(19) 0.0042(15) 0.0202(15) -0.0002(15) C55 0.0481(19) 0.053(2) 0.0331(15) 0.0003(13) -0.0036(13) -0.0100(16) C57 0.103(3) 0.069(2) 0.0464(19) -0.0012(17) 0.036(2) -0.003(2) S2 0.0739(6) 0.0356(4) 0.0378(4) 0.0007(3) 0.0158(4) -0.0023(4) S3 0.0349(4) 0.0548(5) 0.0370(4) -0.0017(3) 0.0101(3) -0.0013(3) O3 0.0390(12) 0.0510(13) 0.0393(11) 0.0072(9) 0.0085(9) 0.0174(10) O2 0.0447(13) 0.0549(15) 0.0416(12) 0.0079(9) 0.0120(9) 0.0165(11) N8 0.0357(14) 0.0446(15) 0.0299(12) 0.0062(10) 0.0037(10) 0.0082(11) N7 0.0304(13) 0.0370(14) 0.0344(12) 0.0030(10) 0.0070(9) 0.0044(11) N5 0.0378(14) 0.0394(14) 0.0339(12) 0.0093(10) 0.0088(10) 0.0087(11) N4 0.0346(14) 0.0433(15) 0.0339(12) 0.0078(10) 0.0065(10) 0.0060(11) C15 0.0281(15) 0.0362(17) 0.0336(14) 0.0041(11) 0.0051(11) 0.0008(13) C19 0.0313(15) 0.0301(16) 0.0353(14) -0.0012(11) 0.0104(11) -0.0038(12) C20 0.0309(15) 0.0348(16) 0.0314(14) 0.0003(11) 0.0030(11) 0.0037(12) C23 0.0332(16) 0.0426(18) 0.0323(14) 0.0043(12) 0.0068(12) -0.0008(14) C24 0.0292(15) 0.0329(17) 0.0412(15) -0.0019(12) 0.0096(11) -0.0049(12) C26 0.0277(15) 0.0359(17) 0.0400(15) -0.0013(12) 0.0086(11) -0.0058(13) C28 0.0305(15) 0.0459(18) 0.0390(15) 0.0028(13) 0.0014(11) 0.0050(13) C30 0.0470(18) 0.0340(16) 0.0476(17) -0.0002(13) 0.0103(13) 0.0009(14) C34 0.0264(15) 0.0373(18) 0.0393(15) -0.0003(12) 0.0058(11) -0.0042(13) C36 0.0330(15) 0.0357(16) 0.0410(15) 0.0053(12) 0.0089(12) 0.0025(13) C37 0.0358(17) 0.0424(19) 0.0423(16) 0.0036(13) 0.0093(13) 0.0031(13) C40 0.0448(18) 0.051(2) 0.0332(15) 0.0021(13) 0.0070(12) 0.0106(15) C41 0.0402(17) 0.0497(19) 0.0351(15) -0.0033(13) 0.0111(12) -0.0031(15) C43 0.052(2) 0.0431(18) 0.0366(15) 0.0013(13) 0.0121(13) 0.0081(15) C44 0.0427(19) 0.0455(19) 0.0507(18) -0.0070(14) 0.0196(14) 0.0001(15) C45 0.0351(17) 0.0413(18) 0.0565(18) -0.0011(14) 0.0169(14) 0.0043(14) C48 0.0439(18) 0.0468(19) 0.0401(16) -0.0008(14) 0.0113(13) -0.0021(15) C49 0.0340(17) 0.0407(18) 0.0438(16) 0.0043(13) 0.0055(13) 0.0022(13) C51 0.0359(17) 0.0419(19) 0.063(2) -0.0042(15) 0.0120(14) 0.0057(15) C52 0.051(2) 0.0436(19) 0.0427(16) -0.0106(14) 0.0052(14) 0.0027(15) C54 0.0468(19) 0.0458(19) 0.0381(16) -0.0002(13) -0.0021(13) 0.0103(15) C56 0.087(3) 0.069(2) 0.0439(18) -0.0017(17) 0.0284(18) 0.001(2) C58 0.046(2) 0.051(2) 0.0545(19) -0.0100(15) 0.0160(15) -0.0014(16) C59 0.067(2) 0.070(2) 0.0388(17) 0.0077(16) 0.0129(15) 0.0120(19) C60 0.072(2) 0.081(3) 0.0426(18) -0.0158(17) 0.0182(17) -0.018(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 S1 C39 1.724(3) . ? S1 C25 1.725(3) . ? S4 C47 1.722(3) . ? S4 C17 1.730(3) . ? O1 C13 1.227(3) . ? O4 C18 1.227(3) . ? N3 C13 1.398(3) . ? N3 C25 1.406(3) . ? N3 C12 1.407(3) . ? N1 C13 1.361(3) . ? N1 C21 1.382(3) . ? N1 H1A 0.8600 . ? N11 C18 1.362(3) . ? N11 C16 1.390(3) . ? N11 H11A 0.8600 . ? N10 C18 1.395(3) . ? N10 C17 1.400(3) . ? N10 C22 1.408(3) . ? C12 C42 1.382(4) . ? C12 C21 1.389(3) . ? C16 C46 1.382(3) . ? C16 C22 1.392(3) . ? C17 C27 1.353(3) . ? C21 C32 1.391(4) . ? C22 C29 1.375(4) . ? C25 C33 1.352(4) . ? C27 C55 1.412(4) . ? C27 H27A 0.9300 . ? C29 C35 1.392(4) . ? C29 H29A 0.9300 . ? C31 C35 1.383(4) . ? C31 C46 1.391(4) . ? C31 H31A 0.9300 . ? C32 C53 1.389(4) . ? C32 H32A 0.9300 . ? C33 C50 1.382(4) . ? C33 H33A 0.9300 . ? C35 H35A 0.9300 . ? C38 C53 1.378(4) . ? C38 C42 1.394(4) . ? C38 H38A 0.9300 . ? C39 C50 1.358(4) . ? C39 C60 1.486(4) . ? C42 H42A 0.9300 . ? C46 H46A 0.9300 . ? C47 C55 1.348(4) . ? C47 C57 1.511(4) . ? C50 H50A 0.9300 . ? C53 H53A 0.9300 . ? C55 H55A 0.9300 . ? C57 H57A 0.9600 . ? C57 H57B 0.9600 . ? C57 H57C 0.9600 . ? S2 C40 1.721(3) . ? S2 C36 1.732(3) . ? S3 C43 1.716(3) . ? S3 C20 1.729(3) . ? O3 C15 1.229(3) . ? O2 C23 1.228(3) . ? N8 C15 1.360(3) . ? N8 C26 1.390(3) . ? N8 H8A 0.8600 . ? N7 C15 1.394(3) . ? N7 C20 1.401(3) . ? N7 C19 1.406(3) . ? N5 C23 1.394(3) . ? N5 C24 1.402(3) . ? N5 C36 1.406(3) . ? N4 C23 1.360(3) . ? N4 C34 1.387(3) . ? N4 H4A 0.8600 . ? C19 C37 1.383(4) . ? C19 C26 1.388(4) . ? C20 C28 1.357(3) . ? C24 C49 1.379(4) . ? C24 C34 1.387(4) . ? C26 C41 1.384(4) . ? C28 C54 1.415(4) . ? C28 H28A 0.9300 . ? C30 C36 1.350(4) . ? C30 C52 1.404(4) . ? C30 H30A 0.9300 . ? C34 C48 1.384(4) . ? C37 C45 1.398(4) . ? C37 H37A 0.9300 . ? C40 C52 1.365(4) . ? C40 C59 1.489(4) . ? C41 C44 1.386(4) . ? C41 H41A 0.9300 . ? C43 C54 1.354(4) . ? C43 C56 1.502(4) . ? C44 C45 1.377(4) . ? C44 H44A 0.9300 . ? C45 H45A 0.9300 . ? C48 C58 1.392(4) . ? C48 H48A 0.9300 . ? C49 C51 1.401(4) . ? C49 H49A 0.9300 . ? C51 C58 1.378(4) . ? C51 H51A 0.9300 . ? C52 H52A 0.9300 . ? C54 H54A 0.9300 . ? C56 H56A 0.9600 . ? C56 H56B 0.9600 . ? C56 H56C 0.9600 . ? C58 H58A 0.9300 . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 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 C39 S1 C25 92.00(14) . . ? C47 S4 C17 91.68(14) . . ? C13 N3 C25 123.0(2) . . ? C13 N3 C12 109.1(2) . . ? C25 N3 C12 127.9(2) . . ? C13 N1 C21 110.5(2) . . ? C13 N1 H1A 124.8 . . ? C21 N1 H1A 124.8 . . ? C18 N11 C16 110.5(2) . . ? C18 N11 H11A 124.8 . . ? C16 N11 H11A 124.8 . . ? C18 N10 C17 124.2(2) . . ? C18 N10 C22 109.4(2) . . ? C17 N10 C22 126.4(2) . . ? C42 C12 C21 121.5(2) . . ? C42 C12 N3 132.2(2) . . ? C21 C12 N3 106.3(2) . . ? O1 C13 N1 128.0(2) . . ? O1 C13 N3 125.7(2) . . ? N1 C13 N3 106.3(2) . . ? C46 C16 N11 131.0(2) . . ? C46 C16 C22 121.4(2) . . ? N11 C16 C22 107.6(2) . . ? C27 C17 N10 127.7(2) . . ? C27 C17 S4 111.6(2) . . ? N10 C17 S4 120.59(19) . . ? O4 C18 N11 128.0(2) . . ? O4 C18 N10 125.7(2) . . ? N11 C18 N10 106.3(2) . . ? N1 C21 C12 107.9(2) . . ? N1 C21 C32 131.0(2) . . ? C12 C21 C32 121.1(3) . . ? C29 C22 C16 121.5(2) . . ? C29 C22 N10 132.2(2) . . ? C16 C22 N10 106.2(2) . . ? C33 C25 N3 128.2(3) . . ? C33 C25 S1 110.3(2) . . ? N3 C25 S1 121.3(2) . . ? C17 C27 C55 111.5(3) . . ? C17 C27 H27A 124.2 . . ? C55 C27 H27A 124.2 . . ? C22 C29 C35 117.2(3) . . ? C22 C29 H29A 121.4 . . ? C35 C29 H29A 121.4 . . ? C35 C31 C46 121.2(3) . . ? C35 C31 H31A 119.4 . . ? C46 C31 H31A 119.4 . . ? C53 C32 C21 117.2(3) . . ? C53 C32 H32A 121.4 . . ? C21 C32 H32A 121.4 . . ? C25 C33 C50 113.7(3) . . ? C25 C33 H33A 123.1 . . ? C50 C33 H33A 123.1 . . ? C31 C35 C29 121.5(3) . . ? C31 C35 H35A 119.3 . . ? C29 C35 H35A 119.3 . . ? C53 C38 C42 121.3(3) . . ? C53 C38 H38A 119.3 . . ? C42 C38 H38A 119.3 . . ? C50 C39 C60 129.3(3) . . ? C50 C39 S1 109.8(2) . . ? C60 C39 S1 120.8(3) . . ? C12 C42 C38 117.2(3) . . ? C12 C42 H42A 121.4 . . ? C38 C42 H42A 121.4 . . ? C16 C46 C31 117.2(3) . . ? C16 C46 H46A 121.4 . . ? C31 C46 H46A 121.4 . . ? C55 C47 C57 129.7(3) . . ? C55 C47 S4 110.2(2) . . ? C57 C47 S4 120.1(3) . . ? C39 C50 C33 114.1(3) . . ? C39 C50 H50A 122.9 . . ? C33 C50 H50A 122.9 . . ? C38 C53 C32 121.6(3) . . ? C38 C53 H53A 119.2 . . ? C32 C53 H53A 119.2 . . ? C47 C55 C27 114.9(3) . . ? C47 C55 H55A 122.5 . . ? C27 C55 H55A 122.5 . . ? C47 C57 H57A 109.5 . . ? C47 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C47 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C40 S2 C36 92.12(15) . . ? C43 S3 C20 92.08(14) . . ? C15 N8 C26 110.5(2) . . ? C15 N8 H8A 124.7 . . ? C26 N8 H8A 124.7 . . ? C15 N7 C20 124.7(2) . . ? C15 N7 C19 109.1(2) . . ? C20 N7 C19 126.2(2) . . ? C23 N5 C24 109.2(2) . . ? C23 N5 C36 123.3(2) . . ? C24 N5 C36 127.4(2) . . ? C23 N4 C34 110.6(2) . . ? C23 N4 H4A 124.7 . . ? C34 N4 H4A 124.7 . . ? O3 C15 N8 128.3(2) . . ? O3 C15 N7 125.3(2) . . ? N8 C15 N7 106.4(2) . . ? C37 C19 C26 121.6(2) . . ? C37 C19 N7 131.8(2) . . ? C26 C19 N7 106.6(2) . . ? C28 C20 N7 127.6(2) . . ? C28 C20 S3 111.5(2) . . ? N7 C20 S3 120.83(19) . . ? O2 C23 N4 127.7(3) . . ? O2 C23 N5 126.2(2) . . ? N4 C23 N5 106.2(2) . . ? C49 C24 C34 121.5(3) . . ? C49 C24 N5 131.9(2) . . ? C34 C24 N5 106.7(2) . . ? C41 C26 C19 121.2(3) . . ? C41 C26 N8 131.4(3) . . ? C19 C26 N8 107.4(2) . . ? C20 C28 C54 111.5(3) . . ? C20 C28 H28A 124.3 . . ? C54 C28 H28A 124.3 . . ? C36 C30 C52 113.3(3) . . ? C36 C30 H30A 123.3 . . ? C52 C30 H30A 123.3 . . ? C48 C34 N4 131.1(2) . . ? C48 C34 C24 121.6(3) . . ? N4 C34 C24 107.3(2) . . ? C30 C36 N5 128.3(3) . . ? C30 C36 S2 110.7(2) . . ? N5 C36 S2 120.9(2) . . ? C19 C37 C45 116.8(3) . . ? C19 C37 H37A 121.6 . . ? C45 C37 H37A 121.6 . . ? C52 C40 C59 129.0(3) . . ? C52 C40 S2 110.2(2) . . ? C59 C40 S2 120.8(2) . . ? C26 C41 C44 117.5(3) . . ? C26 C41 H41A 121.2 . . ? C44 C41 H41A 121.2 . . ? C54 C43 C56 128.9(3) . . ? C54 C43 S3 110.1(2) . . ? C56 C43 S3 121.0(2) . . ? C45 C44 C41 121.3(3) . . ? C45 C44 H44A 119.4 . . ? C41 C44 H44A 119.4 . . ? C44 C45 C37 121.6(3) . . ? C44 C45 H45A 119.2 . . ? C37 C45 H45A 119.2 . . ? C34 C48 C58 117.1(3) . . ? C34 C48 H48A 121.4 . . ? C58 C48 H48A 121.4 . . ? C24 C49 C51 117.0(3) . . ? C24 C49 H49A 121.5 . . ? C51 C49 H49A 121.5 . . ? C58 C51 C49 121.5(3) . . ? C58 C51 H51A 119.3 . . ? C49 C51 H51A 119.3 . . ? C40 C52 C30 113.7(3) . . ? C40 C52 H52A 123.2 . . ? C30 C52 H52A 123.2 . . ? C43 C54 C28 114.8(3) . . ? C43 C54 H54A 122.6 . . ? C28 C54 H54A 122.6 . . ? C43 C56 H56A 109.5 . . ? C43 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C43 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C51 C58 C48 121.3(3) . . ? C51 C58 H58A 119.3 . . ? C48 C58 H58A 119.3 . . ? C40 C59 H59A 109.5 . . ? C40 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C40 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C39 C60 H60A 109.5 . . ? C39 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C39 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.389 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.077