# Electronic Supplementary Material (ESI) for Chemical Science # 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_exp_443 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H62 N4 O10 S2' _chemical_formula_weight 967.18 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 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 7.5487(4) _cell_length_b 12.3687(5) _cell_length_c 13.3085(6) _cell_angle_alpha 86.885(4) _cell_angle_beta 79.430(4) _cell_angle_gamma 78.079(4) _cell_volume 1194.98(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2948 _cell_measurement_theta_min 2.9499 _cell_measurement_theta_max 29.1762 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8867 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0971 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8349 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4702 _reflns_number_gt 3907 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0357P)^2^+0.4967P] 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 4702 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL exp_443 in P-1 #2 CELL 0.71073 7.548685 12.368653 13.308524 86.8852 79.4298 78.0792 ZERR 1 0.000363 0.000514 0.000644 0.0037 0.0041 0.0038 LATT 1 SFAC C H N O S UNIT 52 62 4 10 2 L.S. 4 PLAN 2 SIZE 0.18 0.7 0.5 TEMP -173.15 REM reset to P-1 #2 bond $H conf htab fmap 2 acta OMIT -2 52 REM D:/zhangxi/exp_443/struct/olex2_exp_443/exp_443.hkl WGHT 0.035700 0.496700 FVAR 4.64325 S1 5 0.124701 0.283412 0.877295 11.00000 0.01943 0.01898 = 0.01756 -0.00067 -0.00338 -0.00545 O1 4 0.472803 0.241494 0.511241 11.00000 0.02105 0.02083 = 0.02446 0.00383 -0.00765 -0.01242 O3 4 0.009378 0.383465 0.924370 11.00000 0.02462 0.01703 = 0.03891 -0.00446 -0.00894 -0.00237 O2 4 0.419690 0.340376 0.368956 11.00000 0.03222 0.03347 = 0.02952 0.00992 -0.01607 -0.01875 O4 4 0.240573 0.221157 0.945211 11.00000 0.02592 0.02431 = 0.03302 -0.00033 -0.01285 -0.00151 N1 3 0.875189 0.395999 0.556885 11.00000 0.02361 0.02138 = 0.02158 0.00554 -0.00828 -0.01132 C20 1 -0.033561 0.199050 0.860917 11.00000 0.01930 0.01650 = 0.02078 -0.00179 -0.00235 -0.00237 C18 1 -0.617747 -0.379933 0.933394 11.00000 0.01915 0.02547 = 0.02212 0.00632 -0.00321 -0.00140 AFIX 43 H18 2 -0.721116 -0.335554 0.973974 11.00000 -1.20000 AFIX 0 N2 3 -0.303100 -0.410251 0.856202 11.00000 0.01736 0.01893 = 0.01493 0.00496 -0.00347 -0.00725 C11 1 0.037840 -0.131294 0.669961 11.00000 0.01907 0.01936 = 0.02132 -0.00040 -0.00070 -0.00870 AFIX 23 H11A 2 -0.084985 -0.082760 0.673191 11.00000 -1.20000 H11B 2 0.068612 -0.169835 0.603853 11.00000 -1.20000 AFIX 0 C7 1 0.327616 0.182686 0.503694 11.00000 0.01897 0.02195 = 0.02781 0.00072 -0.00595 -0.01208 AFIX 23 H7A 2 0.352000 0.146486 0.436629 11.00000 -1.20000 H7B 2 0.207271 0.234557 0.510832 11.00000 -1.20000 AFIX 0 C8 1 0.326397 0.097480 0.588964 11.00000 0.01972 0.02022 = 0.02095 -0.00007 -0.00137 -0.00920 AFIX 23 H8A 2 0.294424 0.135351 0.655430 11.00000 -1.20000 H8B 2 0.451171 0.051085 0.584613 11.00000 -1.20000 AFIX 0 C2 1 0.837049 0.509532 0.406355 11.00000 0.02104 0.01660 = 0.01447 0.00187 -0.00115 -0.00724 AFIX 43 H2 2 0.872185 0.566986 0.361713 11.00000 -1.20000 AFIX 0 C4 1 0.649837 0.375064 0.457027 11.00000 0.01670 0.01620 = 0.01804 -0.00047 -0.00174 -0.00541 C12 1 0.028119 -0.217110 0.756562 11.00000 0.02199 0.02100 = 0.01963 0.00004 -0.00304 -0.00918 AFIX 23 H12A 2 0.146978 -0.270410 0.749718 11.00000 -1.20000 H12B 2 0.007972 -0.179741 0.822808 11.00000 -1.20000 AFIX 0 C17 1 -0.634018 -0.477216 0.891703 11.00000 0.02132 0.02698 = 0.02493 0.01306 -0.01122 -0.01177 AFIX 43 H17 2 -0.748343 -0.500707 0.904313 11.00000 -1.20000 AFIX 0 C13 1 -0.126126 -0.279572 0.756160 11.00000 0.01947 0.01974 = 0.01869 0.00295 -0.00409 -0.00788 AFIX 23 H13A 2 -0.245960 -0.227201 0.768781 11.00000 -1.20000 H13B 2 -0.111776 -0.311888 0.687988 11.00000 -1.20000 AFIX 0 C6 1 0.501696 0.318882 0.439367 11.00000 0.01805 0.01688 = 0.02201 0.00047 -0.00290 -0.00622 C10 1 0.178940 -0.059722 0.673081 11.00000 0.01943 0.02157 = 0.02255 -0.00081 -0.00115 -0.00871 AFIX 23 H10A 2 0.146657 -0.019445 0.738297 11.00000 -1.20000 H10B 2 0.301594 -0.108080 0.671243 11.00000 -1.20000 AFIX 0 C3 1 0.698763 0.458223 0.389852 11.00000 0.01828 0.01896 = 0.01647 0.00107 -0.00457 -0.00415 AFIX 43 H3 2 0.637996 0.479602 0.333264 11.00000 -1.20000 AFIX 0 C1 1 0.923694 0.475282 0.489695 11.00000 0.01763 0.01459 = 0.01730 -0.00076 -0.00210 -0.00574 O5 4 0.223214 0.303170 0.775991 11.00000 0.03939 0.04740 = 0.02201 0.00057 -0.00091 -0.02845 C22 1 -0.241885 0.146331 0.765167 11.00000 0.02835 0.02068 = 0.02308 0.00092 -0.00819 -0.00544 AFIX 43 H22 2 -0.294867 0.153565 0.705067 11.00000 -1.20000 AFIX 0 C19 1 -0.449341 -0.348635 0.915053 11.00000 0.02439 0.01766 = 0.01947 0.00323 -0.00369 -0.00511 AFIX 43 H19 2 -0.436458 -0.282903 0.944266 11.00000 -1.20000 AFIX 0 C15 1 -0.316809 -0.503821 0.813636 11.00000 0.02467 0.01961 = 0.01549 0.00349 -0.00624 -0.00591 AFIX 43 H15 2 -0.212862 -0.545449 0.771147 11.00000 -1.20000 AFIX 0 C25 1 -0.087812 0.127441 0.939375 11.00000 0.03443 0.02621 = 0.01978 0.00201 -0.00747 -0.01009 AFIX 43 H25 2 -0.035800 0.120858 0.999778 11.00000 -1.20000 AFIX 0 C21 1 -0.110749 0.207875 0.773146 11.00000 0.02583 0.01688 = 0.02061 0.00305 -0.00420 -0.00602 AFIX 43 H21 2 -0.074008 0.255873 0.718667 11.00000 -1.20000 AFIX 0 C24 1 -0.217444 0.065601 0.929878 11.00000 0.03379 0.02527 = 0.02199 0.00358 0.00172 -0.01141 AFIX 43 H24 2 -0.252029 0.016382 0.983760 11.00000 -1.20000 AFIX 0 C14 1 -0.125403 -0.371431 0.837309 11.00000 0.01645 0.02411 = 0.02038 0.00192 -0.00400 -0.00997 AFIX 23 H14A 2 -0.023355 -0.434151 0.814535 11.00000 -1.20000 H14B 2 -0.104528 -0.343860 0.901746 11.00000 -1.20000 AFIX 0 C16 1 -0.482411 -0.539448 0.831754 11.00000 0.02686 0.02036 = 0.02044 0.00538 -0.01047 -0.01018 AFIX 43 H16 2 -0.491579 -0.606335 0.803079 11.00000 -1.20000 AFIX 0 C23 1 -0.297684 0.074291 0.843019 11.00000 0.02019 0.01662 = 0.02818 -0.00361 0.00060 -0.00338 C26 1 -0.441316 0.008820 0.833213 11.00000 0.02510 0.02403 = 0.03708 -0.00309 0.00052 -0.00913 AFIX 137 H26A 2 -0.563746 0.056405 0.848005 11.00000 -1.50000 H26B 2 -0.433947 -0.053712 0.881795 11.00000 -1.50000 H26C 2 -0.419590 -0.018776 0.763469 11.00000 -1.50000 AFIX 0 C9 1 0.189019 0.023493 0.584399 11.00000 0.02189 0.02123 = 0.02214 0.00014 -0.00125 -0.01001 AFIX 23 H9A 2 0.065515 0.070421 0.585075 11.00000 -1.20000 H9B 2 0.224737 -0.016918 0.519242 11.00000 -1.20000 AFIX 0 C5 1 0.740293 0.348624 0.539581 11.00000 0.02514 0.01899 = 0.02205 0.00719 -0.00700 -0.01095 AFIX 43 H5 2 0.703976 0.293400 0.586687 11.00000 -1.20000 HKLF 4 REM exp_443 in P-1 #2 REM R1 = 0.0397 for 3907 Fo > 4sig(Fo) and 0.0515 for all 4702 data REM 308 parameters refined using 0 restraints END ; 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 0.12470(6) 0.28341(3) 0.87729(3) 0.01839(12) Uani 1 1 d . . . O1 O 0.47280(15) 0.24149(9) 0.51124(9) 0.0206(3) Uani 1 1 d . . . O3 O 0.00938(16) 0.38347(9) 0.92437(10) 0.0265(3) Uani 1 1 d . . . O2 O 0.41969(17) 0.34038(10) 0.36896(10) 0.0290(3) Uani 1 1 d . . . O4 O 0.24057(17) 0.22116(10) 0.94521(10) 0.0273(3) Uani 1 1 d . . . N1 N 0.87519(19) 0.39600(11) 0.55688(11) 0.0209(3) Uani 1 1 d . . . C20 C -0.0336(2) 0.19905(13) 0.86092(14) 0.0191(4) Uani 1 1 d . . . C18 C -0.6177(2) -0.37993(14) 0.93339(14) 0.0230(4) Uani 1 1 d . . . H18 H -0.7211 -0.3356 0.9740 0.028 Uiso 1 1 calc R . . N2 N -0.30310(18) -0.41025(11) 0.85620(11) 0.0167(3) Uani 1 1 d . . . C11 C 0.0378(2) -0.13129(13) 0.66996(13) 0.0196(4) Uani 1 1 d . . . H11A H -0.0850 -0.0828 0.6732 0.023 Uiso 1 1 calc R . . H11B H 0.0686 -0.1698 0.6039 0.023 Uiso 1 1 calc R . . C7 C 0.3276(2) 0.18269(14) 0.50369(14) 0.0215(4) Uani 1 1 d . . . H7A H 0.3520 0.1465 0.4366 0.026 Uiso 1 1 calc R . . H7B H 0.2073 0.2346 0.5108 0.026 Uiso 1 1 calc R . . C8 C 0.3264(2) 0.09748(13) 0.58896(14) 0.0198(4) Uani 1 1 d . . . H8A H 0.2944 0.1354 0.6554 0.024 Uiso 1 1 calc R . . H8B H 0.4512 0.0511 0.5846 0.024 Uiso 1 1 calc R . . C2 C 0.8370(2) 0.50953(13) 0.40636(13) 0.0172(3) Uani 1 1 d . . . H2 H 0.8722 0.5670 0.3617 0.021 Uiso 1 1 calc R . . C4 C 0.6498(2) 0.37506(13) 0.45703(13) 0.0168(3) Uani 1 1 d . . . C12 C 0.0281(2) -0.21711(14) 0.75656(14) 0.0203(4) Uani 1 1 d . . . H12A H 0.1470 -0.2704 0.7497 0.024 Uiso 1 1 calc R . . H12B H 0.0080 -0.1797 0.8228 0.024 Uiso 1 1 calc R . . C17 C -0.6340(2) -0.47722(14) 0.89170(14) 0.0230(4) Uani 1 1 d . . . H17 H -0.7483 -0.5007 0.9043 0.028 Uiso 1 1 calc R . . C13 C -0.1261(2) -0.27957(13) 0.75616(13) 0.0187(4) Uani 1 1 d . . . H13A H -0.2460 -0.2272 0.7688 0.022 Uiso 1 1 calc R . . H13B H -0.1118 -0.3119 0.6880 0.022 Uiso 1 1 calc R . . C6 C 0.5017(2) 0.31888(13) 0.43937(14) 0.0187(4) Uani 1 1 d . . . C10 C 0.1789(2) -0.05972(14) 0.67308(14) 0.0208(4) Uani 1 1 d . . . H10A H 0.1467 -0.0194 0.7383 0.025 Uiso 1 1 calc R . . H10B H 0.3016 -0.1081 0.6712 0.025 Uiso 1 1 calc R . . C3 C 0.6988(2) 0.45822(13) 0.38985(13) 0.0177(4) Uani 1 1 d . . . H3 H 0.6380 0.4796 0.3333 0.021 Uiso 1 1 calc R . . C1 C 0.9237(2) 0.47528(12) 0.48970(13) 0.0162(3) Uani 1 1 d . . . O5 O 0.22321(18) 0.30317(11) 0.77599(10) 0.0340(3) Uani 1 1 d . . . C22 C -0.2419(2) 0.14633(13) 0.76517(14) 0.0235(4) Uani 1 1 d . . . H22 H -0.2949 0.1536 0.7051 0.028 Uiso 1 1 calc R . . C19 C -0.4493(2) -0.34863(13) 0.91505(14) 0.0205(4) Uani 1 1 d . . . H19 H -0.4365 -0.2829 0.9443 0.025 Uiso 1 1 calc R . . C15 C -0.3168(2) -0.50382(13) 0.81364(13) 0.0195(4) Uani 1 1 d . . . H15 H -0.2129 -0.5454 0.7711 0.023 Uiso 1 1 calc R . . C25 C -0.0878(3) 0.12744(14) 0.93937(14) 0.0260(4) Uani 1 1 d . . . H25 H -0.0358 0.1209 0.9998 0.031 Uiso 1 1 calc R . . C21 C -0.1107(2) 0.20788(13) 0.77315(14) 0.0210(4) Uani 1 1 d . . . H21 H -0.0740 0.2559 0.7187 0.025 Uiso 1 1 calc R . . C24 C -0.2174(3) 0.06560(15) 0.92988(15) 0.0272(4) Uani 1 1 d . . . H24 H -0.2520 0.0164 0.9838 0.033 Uiso 1 1 calc R . . C14 C -0.1254(2) -0.37143(14) 0.83731(13) 0.0194(4) Uani 1 1 d . . . H14A H -0.0234 -0.4342 0.8145 0.023 Uiso 1 1 calc R . . H14B H -0.1045 -0.3439 0.9017 0.023 Uiso 1 1 calc R . . C16 C -0.4824(2) -0.53945(14) 0.83175(14) 0.0212(4) Uani 1 1 d . . . H16 H -0.4916 -0.6063 0.8031 0.025 Uiso 1 1 calc R . . C23 C -0.2977(2) 0.07429(13) 0.84302(14) 0.0222(4) Uani 1 1 d . . . C26 C -0.4413(2) 0.00882(15) 0.83321(16) 0.0288(4) Uani 1 1 d . . . H26A H -0.5637 0.0564 0.8480 0.043 Uiso 1 1 calc R . . H26B H -0.4339 -0.0537 0.8818 0.043 Uiso 1 1 calc R . . H26C H -0.4196 -0.0188 0.7635 0.043 Uiso 1 1 calc R . . C9 C 0.1890(2) 0.02349(14) 0.58440(14) 0.0213(4) Uani 1 1 d . . . H9A H 0.0655 0.0704 0.5851 0.026 Uiso 1 1 calc R . . H9B H 0.2247 -0.0169 0.5192 0.026 Uiso 1 1 calc R . . C5 C 0.7403(2) 0.34862(13) 0.53958(14) 0.0210(4) Uani 1 1 d . . . H5 H 0.7040 0.2934 0.5867 0.025 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 0.0194(2) 0.0190(2) 0.0176(2) -0.00067(16) -0.00338(17) -0.00545(17) O1 0.0211(6) 0.0208(6) 0.0245(7) 0.0038(5) -0.0076(5) -0.0124(5) O3 0.0246(7) 0.0170(6) 0.0389(8) -0.0045(5) -0.0089(6) -0.0024(5) O2 0.0322(7) 0.0335(7) 0.0295(8) 0.0099(6) -0.0161(6) -0.0188(6) O4 0.0259(7) 0.0243(6) 0.0330(8) -0.0003(6) -0.0128(6) -0.0015(5) N1 0.0236(8) 0.0214(7) 0.0216(8) 0.0055(6) -0.0083(7) -0.0113(6) C20 0.0193(8) 0.0165(8) 0.0208(9) -0.0018(7) -0.0024(7) -0.0024(7) C18 0.0191(9) 0.0255(9) 0.0221(10) 0.0063(7) -0.0032(8) -0.0014(7) N2 0.0174(7) 0.0189(7) 0.0149(7) 0.0050(6) -0.0035(6) -0.0072(6) C11 0.0191(8) 0.0194(8) 0.0213(9) -0.0004(7) -0.0007(7) -0.0087(7) C7 0.0190(8) 0.0219(8) 0.0278(10) 0.0007(7) -0.0060(8) -0.0121(7) C8 0.0197(8) 0.0202(8) 0.0210(9) -0.0001(7) -0.0014(7) -0.0092(7) C2 0.0210(8) 0.0166(8) 0.0145(9) 0.0019(6) -0.0011(7) -0.0072(7) C4 0.0167(8) 0.0162(8) 0.0180(9) -0.0005(7) -0.0017(7) -0.0054(7) C12 0.0220(9) 0.0210(8) 0.0196(9) 0.0000(7) -0.0030(7) -0.0092(7) C17 0.0213(9) 0.0270(9) 0.0249(10) 0.0131(8) -0.0112(8) -0.0118(8) C13 0.0195(8) 0.0197(8) 0.0187(9) 0.0030(7) -0.0041(7) -0.0079(7) C6 0.0181(8) 0.0169(8) 0.0220(10) 0.0005(7) -0.0029(7) -0.0062(7) C10 0.0194(8) 0.0216(8) 0.0226(10) -0.0008(7) -0.0011(7) -0.0087(7) C3 0.0183(8) 0.0190(8) 0.0165(9) 0.0011(7) -0.0046(7) -0.0042(7) C1 0.0176(8) 0.0146(8) 0.0173(9) -0.0008(7) -0.0021(7) -0.0057(7) O5 0.0394(8) 0.0474(8) 0.0220(7) 0.0006(6) -0.0009(6) -0.0284(7) C22 0.0284(10) 0.0207(8) 0.0231(10) 0.0009(7) -0.0082(8) -0.0054(8) C19 0.0244(9) 0.0177(8) 0.0195(9) 0.0032(7) -0.0037(8) -0.0051(7) C15 0.0247(9) 0.0196(8) 0.0155(9) 0.0035(7) -0.0062(7) -0.0059(7) C25 0.0344(10) 0.0262(9) 0.0198(10) 0.0020(8) -0.0075(8) -0.0101(8) C21 0.0258(9) 0.0169(8) 0.0206(10) 0.0030(7) -0.0042(8) -0.0060(7) C24 0.0338(10) 0.0253(9) 0.0220(10) 0.0036(8) 0.0017(8) -0.0114(8) C14 0.0164(8) 0.0241(8) 0.0204(9) 0.0019(7) -0.0040(7) -0.0100(7) C16 0.0269(9) 0.0204(8) 0.0204(10) 0.0054(7) -0.0105(8) -0.0102(7) C23 0.0202(9) 0.0166(8) 0.0282(10) -0.0036(7) 0.0006(8) -0.0034(7) C26 0.0251(10) 0.0240(9) 0.0371(12) -0.0031(8) 0.0005(9) -0.0091(8) C9 0.0219(9) 0.0212(8) 0.0221(10) 0.0001(7) -0.0012(8) -0.0100(7) C5 0.0251(9) 0.0190(8) 0.0221(10) 0.0072(7) -0.0070(8) -0.0110(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 S1 O5 1.4498(14) . ? S1 O4 1.4530(13) . ? S1 O3 1.4563(12) . ? S1 C20 1.7885(16) . ? O1 C6 1.338(2) . ? O1 C7 1.4553(18) . ? O2 C6 1.204(2) . ? N1 C5 1.334(2) . ? N1 C1 1.352(2) . ? C20 C21 1.388(2) . ? C20 C25 1.391(2) . ? C18 C19 1.380(2) . ? C18 C17 1.389(2) . ? C18 H18 0.9500 . ? N2 C19 1.346(2) . ? N2 C15 1.347(2) . ? N2 C14 1.4907(19) . ? C11 C12 1.526(2) . ? C11 C10 1.526(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C7 C8 1.506(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.529(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C2 C3 1.383(2) . ? C2 C1 1.392(2) . ? C2 H2 0.9500 . ? C4 C5 1.387(2) . ? C4 C3 1.389(2) . ? C4 C6 1.491(2) . ? C12 C13 1.525(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C17 C16 1.381(3) . ? C17 H17 0.9500 . ? C13 C14 1.524(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C10 C9 1.525(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C3 H3 0.9500 . ? C1 C1 1.484(3) 2_766 ? C22 C21 1.389(2) . ? C22 C23 1.393(2) . ? C22 H22 0.9500 . ? C19 H19 0.9500 . ? C15 C16 1.386(2) . ? C15 H15 0.9500 . ? C25 C24 1.387(2) . ? C25 H25 0.9500 . ? C21 H21 0.9500 . ? C24 C23 1.390(3) . ? C24 H24 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 H16 0.9500 . ? C23 C26 1.508(2) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C5 H5 0.9500 . ? 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 O5 S1 O4 113.95(8) . . ? O5 S1 O3 113.00(8) . . ? O4 S1 O3 112.08(8) . . ? O5 S1 C20 106.37(8) . . ? O4 S1 C20 105.91(8) . . ? O3 S1 C20 104.64(7) . . ? C6 O1 C7 116.48(13) . . ? C5 N1 C1 117.19(14) . . ? C21 C20 C25 119.21(15) . . ? C21 C20 S1 121.04(13) . . ? C25 C20 S1 119.67(13) . . ? C19 C18 C17 119.09(17) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C19 N2 C15 121.11(14) . . ? C19 N2 C14 118.46(13) . . ? C15 N2 C14 120.43(14) . . ? C12 C11 C10 113.78(14) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O1 C7 C8 106.85(13) . . ? O1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? O1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C7 C8 C9 112.03(14) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C3 C2 C1 118.67(15) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C5 C4 C3 118.07(14) . . ? C5 C4 C6 122.42(15) . . ? C3 C4 C6 119.50(15) . . ? C13 C12 C11 112.00(14) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C16 C17 C18 119.36(15) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C14 C13 C12 111.77(13) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? O2 C6 O1 124.58(15) . . ? O2 C6 C4 124.08(15) . . ? O1 C6 C4 111.34(14) . . ? C9 C10 C11 112.72(14) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C2 C3 C4 119.19(15) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? N1 C1 C2 122.83(14) . . ? N1 C1 C1 115.70(18) . 2_766 ? C2 C1 C1 121.47(18) . 2_766 ? C21 C22 C23 121.68(17) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? N2 C19 C18 120.72(15) . . ? N2 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? N2 C15 C16 120.06(16) . . ? N2 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C24 C25 C20 120.35(17) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? C20 C21 C22 119.81(16) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C25 C24 C23 121.23(17) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? N2 C14 C13 111.01(13) . . ? N2 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? N2 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C17 C16 C15 119.65(15) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C24 C23 C22 117.71(16) . . ? C24 C23 C26 121.41(16) . . ? C22 C23 C26 120.87(17) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C10 C9 C8 112.84(14) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N1 C5 C4 124.02(15) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? 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 O5 S1 C20 C21 -31.56(16) . . . . ? O4 S1 C20 C21 -153.13(14) . . . . ? O3 S1 C20 C21 88.29(15) . . . . ? O5 S1 C20 C25 151.80(14) . . . . ? O4 S1 C20 C25 30.22(16) . . . . ? O3 S1 C20 C25 -88.36(15) . . . . ? C6 O1 C7 C8 177.58(14) . . . . ? O1 C7 C8 C9 -175.49(13) . . . . ? C10 C11 C12 C13 174.82(14) . . . . ? C19 C18 C17 C16 -0.9(3) . . . . ? C11 C12 C13 C14 175.37(14) . . . . ? C7 O1 C6 O2 -1.9(2) . . . . ? C7 O1 C6 C4 178.46(13) . . . . ? C5 C4 C6 O2 179.47(17) . . . . ? C3 C4 C6 O2 0.4(3) . . . . ? C5 C4 C6 O1 -0.9(2) . . . . ? C3 C4 C6 O1 -179.93(15) . . . . ? C12 C11 C10 C9 178.68(14) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C5 C4 C3 C2 1.3(2) . . . . ? C6 C4 C3 C2 -179.62(15) . . . . ? C5 N1 C1 C2 1.2(2) . . . . ? C5 N1 C1 C1 -178.96(17) . . . 2_766 ? C3 C2 C1 N1 -1.8(2) . . . . ? C3 C2 C1 C1 178.38(18) . . . 2_766 ? C15 N2 C19 C18 0.0(2) . . . . ? C14 N2 C19 C18 178.86(15) . . . . ? C17 C18 C19 N2 1.1(3) . . . . ? C19 N2 C15 C16 -1.3(2) . . . . ? C14 N2 C15 C16 179.87(14) . . . . ? C21 C20 C25 C24 0.0(3) . . . . ? S1 C20 C25 C24 176.74(14) . . . . ? C25 C20 C21 C22 0.7(3) . . . . ? S1 C20 C21 C22 -176.00(13) . . . . ? C23 C22 C21 C20 -0.7(3) . . . . ? C20 C25 C24 C23 -0.8(3) . . . . ? C19 N2 C14 C13 -78.41(18) . . . . ? C15 N2 C14 C13 100.42(17) . . . . ? C12 C13 C14 N2 164.08(14) . . . . ? C18 C17 C16 C15 -0.3(3) . . . . ? N2 C15 C16 C17 1.5(2) . . . . ? C25 C24 C23 C22 0.7(3) . . . . ? C25 C24 C23 C26 -178.83(17) . . . . ? C21 C22 C23 C24 0.0(3) . . . . ? C21 C22 C23 C26 179.54(16) . . . . ? C11 C10 C9 C8 178.40(14) . . . . ? C7 C8 C9 C10 -177.21(14) . . . . ? C1 N1 C5 C4 0.7(3) . . . . ? C3 C4 C5 N1 -2.0(3) . . . . ? C6 C4 C5 N1 178.96(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.328 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 947520'