# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_8 _audit_update_record ; 2011-12-16 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N2 O S2' _chemical_formula_sum 'C24 H24 N2 O S2' _chemical_formula_weight 420.57 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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 11.0980(5) _cell_length_b 6.7887(4) _cell_length_c 15.8764(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.064(5) _cell_angle_gamma 90.00 _cell_volume 1184.32(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 1122 _cell_measurement_theta_min 2.9614 _cell_measurement_theta_max 28.7938 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_min 0.98964 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Multi-scan absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 296(1) _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, Sapphire3' _diffrn_detector_area_resol_mean 16.3990 _diffrn_measurement_method \w-scans _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7220 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2275 _reflns_number_gt 1556 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.2g' _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^ > 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^)+(0.0720P)^2^+0.0711P] 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 2275 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _iucr_refine_instructions_details ; TITL 8, 296K in P2(1)/m CELL 0.71073 11.0980 6.7887 15.8764 90.000 98.064 90.000 ZERR 2.00 0.0005 0.0004 0.0010 0.000 0.005 0.000 LATT 1 SYMM - X, 1/2 + Y, - Z SFAC C H N O S UNIT 48 48 4 2 4 MERG 2 htab C11 O1 htab C12 S2 eqiv $91 -1+x, 1/2-y, z htab C18 N1_$91 mpla FMAP 2 PLAN 10 SIZE 0.05 0.11 0.44 ACTA 50.00 omit -2 50 BOND $H CONF L.S. 4 TEMP 23.00 WGHT 0.072000 0.071100 FVAR 4.25986 O1 4 0.837200 0.250000 0.830396 10.50000 0.06861 0.09611 = 0.03106 0.00000 -0.00413 0.00000 C1 1 0.877307 0.250000 0.752922 10.50000 0.05885 0.07036 = 0.03449 0.00000 0.00192 0.00000 C2 1 0.796769 0.250000 0.681195 10.50000 0.05658 0.05656 = 0.03106 0.00000 0.00355 0.00000 AFIX 43 H2 2 0.825345 0.250000 0.628860 10.50000 -1.20000 AFIX 0 C3 1 0.668870 0.250000 0.683313 10.50000 0.05011 0.03843 = 0.03518 0.00000 0.00524 0.00000 C4 1 0.633990 0.250000 0.766065 10.50000 0.05799 0.05794 = 0.03507 0.00000 0.00722 0.00000 AFIX 43 H4 2 0.551563 0.250000 0.771276 10.50000 -1.20000 AFIX 0 C5 1 0.714797 0.250000 0.836355 10.50000 0.06917 0.06470 = 0.03713 0.00000 0.00824 0.00000 C6 1 1.014073 0.250000 0.762648 10.50000 0.05152 0.11460 = 0.05929 0.00000 -0.00912 0.00000 C7 1 1.060323 0.435800 0.811345 11.00000 0.08427 0.17485 = 0.12274 -0.04560 -0.01120 -0.04189 AFIX 33 H7A 2 1.147631 0.438475 0.818031 11.00000 -1.50000 H7B 2 1.033770 0.435407 0.866347 11.00000 -1.50000 H7C 2 1.028588 0.550099 0.780212 11.00000 -1.50000 AFIX 0 C8 1 1.057910 0.250000 0.676196 10.50000 0.04697 0.19107 = 0.08289 0.00000 0.01224 0.00000 AFIX 3 H8A 2 1.145262 0.250000 0.683706 10.50000 -1.50000 H8B 2 1.028073 0.365462 0.645122 11.00000 -1.50000 AFIX 0 C9 1 0.691925 0.250000 0.928165 10.50000 0.09260 0.12955 = 0.02639 0.00000 0.01230 0.00000 C10 1 0.557178 0.250000 0.933265 10.50000 0.12950 0.17769 = 0.05549 0.00000 0.04813 0.00000 AFIX 3 H10A 2 0.541420 0.250000 0.994141 10.50000 -1.50000 H10B 2 0.526075 0.384573 0.914006 11.00000 -1.50000 AFIX 0 C11 1 0.745693 0.436188 0.970015 11.00000 0.22654 0.27677 = 0.07760 -0.10231 0.06385 -0.12061 AFIX 33 H11A 2 0.706644 0.548677 0.941443 11.00000 -1.50000 H11B 2 0.831317 0.440522 0.966539 11.00000 -1.50000 H11C 2 0.733274 0.437637 1.028647 11.00000 -1.50000 AFIX 0 C12 1 0.580442 0.250000 0.612070 10.50000 0.04366 0.04511 = 0.03667 0.00000 0.00544 0.00000 AFIX 43 H12 2 0.499591 0.250000 0.621463 10.50000 -1.20000 AFIX 0 C13 1 0.602270 0.250000 0.528238 10.50000 0.03809 0.04221 = 0.03487 0.00000 0.00509 0.00000 AFIX 43 H13 2 0.683196 0.250000 0.519022 10.50000 -1.20000 AFIX 0 C14 1 0.514801 0.250000 0.457012 10.50000 0.03392 0.03768 = 0.03249 0.00000 0.00187 0.00000 C15 1 0.539845 0.250000 0.370677 10.50000 0.04471 0.04104 = 0.03463 0.00000 -0.00205 0.00000 S1 5 0.407168 0.250000 0.297443 10.50000 0.05974 0.05797 = 0.03740 0.00000 -0.01089 0.00000 C16 1 0.316667 0.250000 0.377869 10.50000 0.04784 0.04212 = 0.05111 0.00000 -0.00502 0.00000 C17 1 0.189550 0.250000 0.378817 10.50000 0.04086 0.07552 = 0.08246 0.00000 -0.01567 0.00000 AFIX 43 H17 2 0.131536 0.250000 0.330477 10.50000 -1.20000 AFIX 0 C18 1 0.163898 0.250000 0.458939 10.50000 0.03605 0.08732 = 0.10639 0.00000 0.00979 0.00000 AFIX 43 H18 2 0.084937 0.250000 0.472284 10.50000 -1.20000 AFIX 0 S2 5 0.290542 0.250000 0.534286 10.50000 0.04216 0.07829 = 0.06618 0.00000 0.01621 0.00000 C19 1 0.384018 0.250000 0.456622 10.50000 0.03950 0.03856 = 0.04585 0.00000 0.00288 0.00000 C20 1 0.650186 0.250000 0.337821 10.50000 0.05347 0.06839 = 0.03510 0.00000 0.00873 0.00000 C21 1 0.766770 0.250000 0.387625 10.50000 0.05173 0.07922 = 0.05441 0.00000 0.02567 0.00000 N1 3 0.861424 0.250000 0.426105 10.50000 0.04400 0.12933 = 0.09814 0.00000 0.01576 0.00000 C22 1 0.649248 0.250000 0.248258 10.50000 0.07598 0.13294 = 0.04845 0.00000 0.01570 0.00000 N2 3 0.643364 0.250000 0.176196 10.50000 0.12580 0.26602 = 0.04489 0.00000 0.02509 0.00000 HKLF 4 REM 8, 296K in P2(1)/m REM R1 = 0.0552 for 1556 Fo > 4sig(Fo) and 0.0892 for all 2275 data REM 169 parameters refined using 0 restraints END WGHT 0.0571 0.0400 REM Highest difference peak 0.292, deepest hole -0.207, 1-sigma level 0.041 Q1 1 0.2526 0.2500 0.4759 10.50000 0.05 0.29 Q2 1 0.8000 0.2500 0.9804 10.50000 0.05 0.27 Q3 1 0.8523 0.2500 0.9871 10.50000 0.05 0.24 Q4 1 0.4802 0.2500 0.3375 10.50000 0.05 0.21 Q5 1 0.4430 0.2500 0.4652 10.50000 0.05 0.20 Q6 1 0.3249 0.1891 0.3173 11.00000 0.05 0.20 Q7 1 0.3674 0.2500 0.4118 10.50000 0.05 0.19 Q8 1 0.8006 0.5336 0.9530 11.00000 0.05 0.18 Q9 1 0.7378 0.4897 1.0039 11.00000 0.05 0.17 Q10 1 0.5000 0.2500 0.7589 10.50000 0.05 0.16 ; 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 O1 O 0.8372(3) 0.2500 0.83040(17) 0.0663(8) Uani 1 2 d S . . C1 C 0.8773(4) 0.2500 0.7529(3) 0.0550(10) Uani 1 2 d S . . C2 C 0.7968(3) 0.2500 0.6812(2) 0.0483(9) Uani 1 2 d S . . H2 H 0.8253 0.2500 0.6289 0.058 Uiso 1 2 calc SR . . C3 C 0.6689(3) 0.2500 0.6833(2) 0.0413(8) Uani 1 2 d S . . C4 C 0.6340(4) 0.2500 0.7661(2) 0.0503(9) Uani 1 2 d S . . H4 H 0.5516 0.2500 0.7713 0.060 Uiso 1 2 calc SR . . C5 C 0.7148(4) 0.2500 0.8364(3) 0.0569(10) Uani 1 2 d S . . C6 C 1.0141(4) 0.2500 0.7626(3) 0.0768(13) Uani 1 2 d S . . C7 C 1.0603(4) 0.4358(7) 0.8113(3) 0.1297(17) Uani 1 1 d . . . H7A H 1.1476 0.4385 0.8180 0.195 Uiso 1 1 calc R . . H7B H 1.0338 0.4354 0.8663 0.195 Uiso 1 1 calc R . . H7C H 1.0286 0.5501 0.7802 0.195 Uiso 1 1 calc R . . C8 C 1.0579(4) 0.2500 0.6762(4) 0.1067(19) Uani 1 2 d S . . H8A H 1.1453 0.2500 0.6837 0.160 Uiso 1 2 d SR . . H8B H 1.0281 0.3655 0.6451 0.160 Uiso 1 1 d R . . C9 C 0.6919(5) 0.2500 0.9282(3) 0.0825(15) Uani 1 2 d S . . C10 C 0.5572(6) 0.2500 0.9333(3) 0.118(2) Uani 1 2 d S . . H10A H 0.5414 0.2500 0.9941 0.176 Uiso 1 2 d SR . . H10B H 0.5261 0.3846 0.9140 0.176 Uiso 1 1 d R . . C11 C 0.7457(5) 0.4362(9) 0.9700(3) 0.190(3) Uani 1 1 d . . . H11A H 0.7066 0.5487 0.9414 0.284 Uiso 1 1 calc R . . H11B H 0.8313 0.4405 0.9665 0.284 Uiso 1 1 calc R . . H11C H 0.7333 0.4376 1.0286 0.284 Uiso 1 1 calc R . . C12 C 0.5804(3) 0.2500 0.6121(2) 0.0418(8) Uani 1 2 d S . . H12 H 0.4996 0.2500 0.6215 0.050 Uiso 1 2 calc SR . . C13 C 0.6023(3) 0.2500 0.5282(2) 0.0384(8) Uani 1 2 d S . . H13 H 0.6832 0.2500 0.5190 0.046 Uiso 1 2 calc SR . . C14 C 0.5148(3) 0.2500 0.4570(2) 0.0350(8) Uani 1 2 d S . . C15 C 0.5398(3) 0.2500 0.3707(2) 0.0409(9) Uani 1 2 d S . . S1 S 0.40717(9) 0.2500 0.29744(6) 0.0534(3) Uani 1 2 d S . . C16 C 0.3167(3) 0.2500 0.3779(3) 0.0482(9) Uani 1 2 d S . . C17 C 0.1896(4) 0.2500 0.3788(3) 0.0686(13) Uani 1 2 d S . . H17 H 0.1315 0.2500 0.3305 0.082 Uiso 1 2 calc SR . . C18 C 0.1639(4) 0.2500 0.4589(4) 0.0766(14) Uani 1 2 d S . . H18 H 0.0849 0.2500 0.4723 0.092 Uiso 1 2 calc SR . . S2 S 0.29054(9) 0.2500 0.53429(7) 0.0614(4) Uani 1 2 d S . . C19 C 0.3840(3) 0.2500 0.4566(2) 0.0416(9) Uani 1 2 d S . . C20 C 0.6502(4) 0.2500 0.3378(2) 0.0521(10) Uani 1 2 d S . . C21 C 0.7668(4) 0.2500 0.3876(3) 0.0601(11) Uani 1 2 d S . . N1 N 0.8614(3) 0.2500 0.4261(3) 0.0899(13) Uani 1 2 d S . . C22 C 0.6492(5) 0.2500 0.2483(3) 0.0851(15) Uani 1 2 d S . . N2 N 0.6434(5) 0.2500 0.1762(3) 0.144(2) Uani 1 2 d S . . 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 O1 0.069(2) 0.096(2) 0.0311(17) 0.000 -0.0041(14) 0.000 C1 0.059(3) 0.070(3) 0.034(2) 0.000 0.002(2) 0.000 C2 0.057(2) 0.057(2) 0.031(2) 0.000 0.0036(18) 0.000 C3 0.050(2) 0.0384(19) 0.035(2) 0.000 0.0052(17) 0.000 C4 0.058(2) 0.058(2) 0.035(2) 0.000 0.0072(19) 0.000 C5 0.069(3) 0.065(3) 0.037(3) 0.000 0.008(2) 0.000 C6 0.052(3) 0.115(4) 0.059(3) 0.000 -0.009(2) 0.000 C7 0.084(3) 0.175(4) 0.123(4) -0.046(3) -0.011(3) -0.042(3) C8 0.047(3) 0.191(6) 0.083(4) 0.000 0.012(3) 0.000 C9 0.093(4) 0.130(4) 0.026(3) 0.000 0.012(2) 0.000 C10 0.129(5) 0.178(6) 0.055(4) 0.000 0.048(4) 0.000 C11 0.227(6) 0.277(7) 0.078(4) -0.102(4) 0.064(4) -0.121(5) C12 0.044(2) 0.045(2) 0.037(2) 0.000 0.0054(17) 0.000 C13 0.0381(19) 0.0422(19) 0.035(2) 0.000 0.0051(16) 0.000 C14 0.0339(18) 0.0377(18) 0.032(2) 0.000 0.0019(15) 0.000 C15 0.045(2) 0.041(2) 0.035(2) 0.000 -0.0020(17) 0.000 S1 0.0597(7) 0.0580(6) 0.0374(6) 0.000 -0.0109(5) 0.000 C16 0.048(2) 0.042(2) 0.051(3) 0.000 -0.0050(19) 0.000 C17 0.041(2) 0.076(3) 0.082(4) 0.000 -0.016(2) 0.000 C18 0.036(2) 0.087(3) 0.106(5) 0.000 0.010(3) 0.000 S2 0.0422(6) 0.0783(8) 0.0662(8) 0.000 0.0162(5) 0.000 C19 0.040(2) 0.039(2) 0.046(2) 0.000 0.0029(17) 0.000 C20 0.053(2) 0.068(2) 0.035(2) 0.000 0.0087(19) 0.000 C21 0.052(3) 0.079(3) 0.054(3) 0.000 0.026(2) 0.000 N1 0.044(2) 0.129(4) 0.098(4) 0.000 0.016(2) 0.000 C22 0.076(3) 0.133(4) 0.048(3) 0.000 0.016(3) 0.000 N2 0.126(5) 0.266(7) 0.045(3) 0.000 0.025(3) 0.000 _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 O1 C1 1.366(5) . ? O1 C5 1.375(5) . ? C1 C2 1.345(5) . ? C1 C6 1.504(6) . ? C2 C3 1.425(5) . ? C2 H2 0.9300 . ? C3 C12 1.390(5) . ? C3 C4 1.421(5) . ? C4 C5 1.330(5) . ? C4 H4 0.9300 . ? C5 C9 1.514(6) . ? C6 C8 1.519(7) . ? C6 C7 1.530(4) . ? C6 C7 1.530(4) 4_565 ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C9 C10 1.509(7) . ? C9 C11 1.511(5) . ? C9 C11 1.511(5) 4_565 ? C10 H10A 1.0060 . ? C10 H10B 1.0088 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.386(5) . ? C12 H12 0.9300 . ? C13 C14 1.383(4) . ? C13 H13 0.9300 . ? C14 C15 1.436(5) . ? C14 C19 1.451(5) . ? C15 C20 1.397(5) . ? C15 S1 1.743(3) . ? S1 C16 1.732(4) . ? C16 C19 1.364(5) . ? C16 C17 1.413(5) . ? C17 C18 1.342(6) . ? C17 H17 0.9300 . ? C18 S2 1.713(5) . ? C18 H18 0.9300 . ? S2 C19 1.719(4) . ? C20 C21 1.419(6) . ? C20 C22 1.421(6) . ? C21 N1 1.139(5) . ? C22 N2 1.137(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 C1 O1 C5 120.8(3) . . ? C2 C1 O1 120.0(4) . . ? C2 C1 C6 128.9(4) . . ? O1 C1 C6 111.1(4) . . ? C1 C2 C3 121.7(4) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C12 C3 C4 120.0(3) . . ? C12 C3 C2 125.0(3) . . ? C4 C3 C2 115.1(3) . . ? C5 C4 C3 122.5(4) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 O1 119.9(4) . . ? C4 C5 C9 128.6(4) . . ? O1 C5 C9 111.5(4) . . ? C1 C6 C8 110.7(4) . . ? C1 C6 C7 108.3(3) . . ? C8 C6 C7 109.2(3) . . ? C1 C6 C7 108.3(3) . 4_565 ? C8 C6 C7 109.2(3) . 4_565 ? C7 C6 C7 111.1(5) . 4_565 ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C10 C9 C11 108.0(3) . . ? C10 C9 C11 108.0(3) . 4_565 ? C11 C9 C11 113.5(6) . 4_565 ? C10 C9 C5 110.7(4) . . ? C11 C9 C5 108.3(3) . . ? C11 C9 C5 108.3(3) 4_565 . ? C9 C10 H10A 111.0 . . ? C9 C10 H10B 106.5 . . ? H10A C10 H10B 101.1 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C3 125.7(3) . . ? C13 C12 H12 117.2 . . ? C3 C12 H12 117.2 . . ? C14 C13 C12 126.0(3) . . ? C14 C13 H13 117.0 . . ? C12 C13 H13 117.0 . . ? C13 C14 C15 124.9(3) . . ? C13 C14 C19 126.2(3) . . ? C15 C14 C19 108.9(3) . . ? C20 C15 C14 130.8(3) . . ? C20 C15 S1 117.0(3) . . ? C14 C15 S1 112.2(2) . . ? C16 S1 C15 91.79(17) . . ? C19 C16 C17 114.2(4) . . ? C19 C16 S1 112.1(3) . . ? C17 C16 S1 133.7(4) . . ? C18 C17 C16 110.8(4) . . ? C18 C17 H17 124.6 . . ? C16 C17 H17 124.6 . . ? C17 C18 S2 113.6(3) . . ? C17 C18 H18 123.2 . . ? S2 C18 H18 123.2 . . ? C18 S2 C19 91.0(2) . . ? C16 C19 C14 115.0(3) . . ? C16 C19 S2 110.4(3) . . ? C14 C19 S2 134.5(3) . . ? C15 C20 C21 124.8(3) . . ? C15 C20 C22 119.4(4) . . ? C21 C20 C22 115.8(4) . . ? N1 C21 C20 178.6(5) . . ? N2 C22 C20 177.2(6) . . ? 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 C5 O1 C1 C2 0.000(2) . . . . ? C5 O1 C1 C6 180.000(1) . . . . ? O1 C1 C2 C3 0.000(2) . . . . ? C6 C1 C2 C3 180.000(1) . . . . ? C1 C2 C3 C12 180.000(1) . . . . ? C1 C2 C3 C4 0.000(1) . . . . ? C12 C3 C4 C5 180.000(2) . . . . ? C2 C3 C4 C5 0.000(2) . . . . ? C3 C4 C5 O1 0.000(2) . . . . ? C3 C4 C5 C9 180.000(2) . . . . ? C1 O1 C5 C4 0.000(2) . . . . ? C1 O1 C5 C9 180.000(2) . . . . ? C2 C1 C6 C8 0.000(2) . . . . ? O1 C1 C6 C8 180.000(1) . . . . ? C2 C1 C6 C7 119.7(3) . . . . ? O1 C1 C6 C7 -60.3(3) . . . . ? C2 C1 C6 C7 -119.7(3) . . . 4_565 ? O1 C1 C6 C7 60.3(3) . . . 4_565 ? C4 C5 C9 C10 0.000(2) . . . . ? O1 C5 C9 C10 180.000(2) . . . . ? C4 C5 C9 C11 -118.2(4) . . . . ? O1 C5 C9 C11 61.8(4) . . . . ? C4 C5 C9 C11 118.2(4) . . . 4_565 ? O1 C5 C9 C11 -61.8(4) . . . 4_565 ? C4 C3 C12 C13 180.000(1) . . . . ? C2 C3 C12 C13 0.000(1) . . . . ? C3 C12 C13 C14 180.000(1) . . . . ? C12 C13 C14 C15 180.0 . . . . ? C12 C13 C14 C19 0.000(1) . . . . ? C13 C14 C15 C20 0.000(1) . . . . ? C19 C14 C15 C20 180.0 . . . . ? C13 C14 C15 S1 180.0 . . . . ? C19 C14 C15 S1 0.0 . . . . ? C20 C15 S1 C16 180.0 . . . . ? C14 C15 S1 C16 0.0 . . . . ? C15 S1 C16 C19 0.0 . . . . ? C15 S1 C16 C17 180.0 . . . . ? C19 C16 C17 C18 0.0 . . . . ? S1 C16 C17 C18 180.0 . . . . ? C16 C17 C18 S2 0.0 . . . . ? C17 C18 S2 C19 0.0 . . . . ? C17 C16 C19 C14 180.0 . . . . ? S1 C16 C19 C14 0.0 . . . . ? C17 C16 C19 S2 0.0 . . . . ? S1 C16 C19 S2 180.0 . . . . ? C13 C14 C19 C16 180.0 . . . . ? C15 C14 C19 C16 0.0 . . . . ? C13 C14 C19 S2 0.0 . . . . ? C15 C14 C19 S2 180.0 . . . . ? C18 S2 C19 C16 0.0 . . . . ? C18 S2 C19 C14 180.0 . . . . ? C14 C15 C20 C21 0.000(1) . . . . ? S1 C15 C20 C21 180.0 . . . . ? C14 C15 C20 C22 180.0 . . . . ? S1 C15 C20 C22 0.0 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C11 H11B O1 0.96 2.53 2.859(5) 100.3 . C12 H12 S2 0.93 2.53 3.280(4) 138.1 . C18 H18 N1 0.93 2.49 3.324(6) 150.0 4_465 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.292 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 943682' ####################################################################### # # 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_14 _audit_update_record ; 2012-02-10 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 N3 S2' _chemical_formula_sum 'C20 H17 N3 S2' _chemical_formula_weight 363.49 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3982(4) _cell_length_b 25.3341(19) _cell_length_c 17.1667(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.599(5) _cell_angle_gamma 90.00 _cell_volume 3620.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2217 _cell_measurement_theta_min 2.8569 _cell_measurement_theta_max 28.9160 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_T_min 0.93025 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Multi-scan absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 150(1) _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, Sapphire3' _diffrn_detector_area_resol_mean 16.3990 _diffrn_measurement_method \w-scans _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24610 _diffrn_reflns_av_R_equivalents 0.0972 _diffrn_reflns_av_sigmaI/netI 0.1104 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6357 _reflns_number_gt 3793 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamong 3.2g' _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^ > 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^)+(0.0479P)^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 6357 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL 14, P 21/c, 150K CELL 0.71073 8.3982 25.3341 17.1667 90.000 97.599 90.000 ZERR 8.00 0.0004 0.0019 0.0011 0.000 0.005 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N S UNIT 160 136 24 16 MERG 2 FMAP 2 PLAN 15 ACTA 50 omit -2 50 temp -123 size 0.47 0.14 0.03 htab conf eqiv $91 -1+x, 1/2 - y, -1/2 +z htab c2 n5_$91 htab c12 s2 htab c32 s4 bond $h mpla L.S. 4 WGHT 0.047900 FVAR 1.20614 S1 4 0.028675 0.050053 0.087907 11.00000 0.02613 0.02744 = 0.02259 -0.00218 0.00121 0.00019 C1 1 -0.052857 0.113573 0.077655 11.00000 0.01841 0.02639 = 0.02108 0.00007 0.00778 -0.00551 C2 1 0.007894 0.147468 0.140764 11.00000 0.01784 0.02283 = 0.02733 0.00026 0.00822 -0.00015 AFIX 43 H2 2 -0.022748 0.183305 0.145464 11.00000 -1.20000 AFIX 0 C3 1 0.117026 0.121327 0.194072 11.00000 0.01938 0.02605 = 0.02201 -0.00029 0.01047 -0.00436 S2 4 0.234571 0.139255 0.280948 11.00000 0.02672 0.02757 = 0.02182 -0.00273 0.00147 0.00095 C4 1 0.323549 0.075930 0.290288 11.00000 0.02108 0.02555 = 0.02217 -0.00489 0.00885 -0.00269 C5 1 0.261376 0.043180 0.226385 11.00000 0.02109 0.02554 = 0.02095 -0.00035 0.00747 0.00059 AFIX 43 H5 2 0.294933 0.007771 0.220364 11.00000 -1.20000 AFIX 0 C6 1 0.148026 0.067920 0.174326 11.00000 0.01986 0.02220 = 0.02166 -0.00253 0.00626 -0.00144 C7 1 -0.162035 0.126670 0.011548 11.00000 0.01702 0.03250 = 0.02044 0.00118 0.00455 0.00410 C8 1 -0.210504 0.089005 -0.048305 11.00000 0.02002 0.02701 = 0.02201 0.00621 0.00339 0.00102 N1 3 -0.245732 0.058070 -0.096088 11.00000 0.03662 0.03536 = 0.03310 -0.00574 -0.00209 0.00122 C9 1 -0.220008 0.179611 0.000535 11.00000 0.01933 0.03695 = 0.01857 0.00227 0.00166 -0.00232 N2 3 -0.262006 0.222400 -0.007860 11.00000 0.03975 0.03671 = 0.04550 0.00480 0.00369 0.00882 C10 1 0.436162 0.058298 0.350864 11.00000 0.02098 0.02661 = 0.02221 0.00220 0.01266 -0.00284 AFIX 43 H10 2 0.471418 0.023200 0.343797 11.00000 -1.20000 AFIX 0 C11 1 0.510282 0.082372 0.422136 11.00000 0.01833 0.02725 = 0.02007 -0.00114 0.00494 -0.00121 C12 1 0.491701 0.135189 0.444487 11.00000 0.02102 0.02647 = 0.02972 0.00495 0.00330 -0.00008 AFIX 43 H12 2 0.429482 0.158365 0.409120 11.00000 -1.20000 AFIX 0 C13 1 0.560603 0.154188 0.515680 11.00000 0.02777 0.02871 = 0.02485 -0.00005 0.00205 0.00204 AFIX 43 H13 2 0.548983 0.190455 0.527817 11.00000 -1.20000 AFIX 0 C14 1 0.649412 0.120429 0.571817 11.00000 0.01664 0.03459 = 0.01873 0.00043 0.00364 -0.00305 C15 1 0.672831 0.068007 0.548328 11.00000 0.02272 0.03002 = 0.02217 0.00685 0.00148 0.00301 AFIX 43 H15 2 0.734676 0.044531 0.583358 11.00000 -1.20000 AFIX 0 C16 1 0.607898 0.050625 0.476064 11.00000 0.01909 0.02557 = 0.02971 -0.00087 0.00823 -0.00035 AFIX 43 H16 2 0.629515 0.015450 0.461402 11.00000 -1.20000 AFIX 0 N3 3 0.708500 0.138087 0.645339 11.00000 0.03192 0.02712 = 0.02144 0.00338 -0.00209 0.00253 C17 1 0.712695 0.193531 0.668420 11.00000 0.04562 0.03322 = 0.02335 0.00296 -0.00327 -0.00506 AFIX 23 H17A 2 0.721431 0.215513 0.621492 11.00000 -1.20000 H17B 2 0.810042 0.199810 0.706523 11.00000 -1.20000 AFIX 0 C18 1 0.567562 0.210976 0.704689 11.00000 0.05974 0.04029 = 0.06233 -0.00016 0.01997 0.00355 AFIX 33 H18A 2 0.578349 0.248394 0.718886 11.00000 -1.50000 H18B 2 0.559200 0.189990 0.751933 11.00000 -1.50000 H18C 2 0.470720 0.205891 0.666843 11.00000 -1.50000 AFIX 0 C19 1 0.750094 0.100093 0.709825 11.00000 0.03097 0.03778 = 0.02036 0.00602 0.00504 -0.00008 AFIX 23 H19A 2 0.688118 0.067204 0.697648 11.00000 -1.20000 H19B 2 0.718115 0.114958 0.758786 11.00000 -1.20000 AFIX 0 C20 1 0.927603 0.086866 0.723397 11.00000 0.03381 0.04396 = 0.03119 0.00399 -0.00268 -0.00133 AFIX 33 H20A 2 0.948211 0.061441 0.766578 11.00000 -1.50000 H20B 2 0.989627 0.119106 0.736929 11.00000 -1.50000 H20C 2 0.959749 0.071498 0.675461 11.00000 -1.50000 AFIX 0 S3 4 1.098976 0.062373 0.483907 11.00000 0.02682 0.03295 = 0.03346 -0.00005 0.00083 0.00492 C21 1 1.082790 0.126570 0.521401 11.00000 0.02449 0.03027 = 0.02989 0.00341 0.01139 -0.00285 C22 1 0.975052 0.158630 0.471037 11.00000 0.01691 0.02951 = 0.02170 0.00643 0.00612 -0.00087 AFIX 43 H22 2 0.948674 0.194127 0.481768 11.00000 -1.20000 AFIX 0 C23 1 0.914269 0.131177 0.404637 11.00000 0.01669 0.03143 = 0.02862 0.00514 0.00973 0.00088 S4 4 0.784505 0.147157 0.320785 11.00000 0.02692 0.03130 = 0.02930 0.00111 0.00375 0.00198 C24 1 0.794170 0.082289 0.284671 11.00000 0.02214 0.02705 = 0.03233 -0.00155 0.01120 0.00038 C25 1 0.901407 0.050427 0.336720 11.00000 0.02544 0.02844 = 0.02997 -0.00001 0.00910 -0.00688 AFIX 43 H25 2 0.924828 0.014505 0.327141 11.00000 -1.20000 AFIX 0 C26 1 0.965660 0.077683 0.401426 11.00000 0.02089 0.02630 = 0.03417 0.00300 0.01099 0.00281 C27 1 1.170658 0.138844 0.593495 11.00000 0.02223 0.03116 = 0.02631 -0.00254 0.00541 -0.00474 C28 1 1.273525 0.100044 0.633944 11.00000 0.02249 0.03623 = 0.01945 0.00098 0.00659 0.00042 N4 3 1.352456 0.066962 0.663869 11.00000 0.03211 0.03975 = 0.03400 -0.00141 0.00134 0.00560 C29 1 1.151411 0.188098 0.630183 11.00000 0.03023 0.03932 = 0.02827 0.00201 -0.00107 0.00126 N5 3 1.133696 0.227927 0.660605 11.00000 0.05721 0.03869 = 0.05384 -0.00513 -0.00602 0.00702 C30 1 0.710728 0.062329 0.216290 11.00000 0.02236 0.02470 = 0.03142 0.00005 0.01221 -0.00098 AFIX 43 H30 2 0.732207 0.026165 0.207395 11.00000 -1.20000 AFIX 0 C31 1 0.598555 0.085566 0.156486 11.00000 0.02589 0.02671 = 0.02530 0.00265 0.01192 0.00093 C32 1 0.549139 0.138710 0.153583 11.00000 0.03185 0.02982 = 0.02902 -0.00411 0.00332 -0.00138 AFIX 43 H32 2 0.594635 0.162150 0.193663 11.00000 -1.20000 AFIX 0 C33 1 0.437404 0.157753 0.094749 11.00000 0.03593 0.02517 = 0.02447 -0.00177 0.00617 0.00546 AFIX 43 H33 2 0.408090 0.193967 0.094914 11.00000 -1.20000 AFIX 0 C34 1 0.364619 0.124427 0.033572 11.00000 0.02123 0.03265 = 0.02159 0.00018 0.01126 -0.00124 C35 1 0.416363 0.071585 0.035659 11.00000 0.02953 0.03264 = 0.01809 -0.00770 0.00534 -0.00072 AFIX 43 H35 2 0.373824 0.048418 -0.005408 11.00000 -1.20000 AFIX 0 C36 1 0.526476 0.052443 0.095225 11.00000 0.03421 0.02884 = 0.02741 -0.00447 0.01172 0.00370 AFIX 43 H36 2 0.554993 0.016152 0.095366 11.00000 -1.20000 AFIX 0 N6 3 0.250691 0.143004 -0.023958 11.00000 0.02712 0.03092 = 0.02308 -0.00098 0.00252 -0.00044 C37 1 0.193640 0.197585 -0.025728 11.00000 0.02602 0.03602 = 0.03665 0.00406 0.00325 0.00317 AFIX 23 H37A 2 0.198190 0.210446 0.028978 11.00000 -1.20000 H37B 2 0.079747 0.198226 -0.049670 11.00000 -1.20000 AFIX 0 C38 1 0.287577 0.234972 -0.070524 11.00000 0.03863 0.03478 = 0.07451 0.00923 0.01698 -0.00480 AFIX 33 H38A 2 0.242380 0.270561 -0.068949 11.00000 -1.50000 H38B 2 0.281313 0.223251 -0.125248 11.00000 -1.50000 H38C 2 0.400120 0.235417 -0.046505 11.00000 -1.50000 AFIX 0 C39 1 0.193907 0.109747 -0.091719 11.00000 0.03239 0.04655 = 0.02369 -0.00231 0.00000 -0.00175 AFIX 23 H39A 2 0.093614 0.125077 -0.119390 11.00000 -1.20000 H39B 2 0.167935 0.074293 -0.072673 11.00000 -1.20000 AFIX 0 C40 1 0.314479 0.103851 -0.149757 11.00000 0.04666 0.05848 = 0.02552 -0.00339 0.00812 0.00159 AFIX 33 H40A 2 0.268913 0.081316 -0.193505 11.00000 -1.50000 H40B 2 0.413188 0.087747 -0.123296 11.00000 -1.50000 H40C 2 0.339129 0.138687 -0.169914 11.00000 -1.50000 HKLF 4 REM 14, P 21/c, 150K REM R1 = 0.0654 for 3793 Fo > 4sig(Fo) and 0.1243 for all 6357 data REM 451 parameters refined using 0 restraints END WGHT 0.0356 0.1888 REM Highest difference peak 0.327, deepest hole -0.273, 1-sigma level 0.074 Q1 1 0.3546 -0.0452 0.1845 11.00000 0.05 0.33 Q2 1 1.2431 0.0593 0.5015 11.00000 0.05 0.30 Q3 1 0.8813 0.1338 0.3603 11.00000 0.05 0.30 Q4 1 0.2869 0.1674 0.3294 11.00000 0.05 0.29 Q5 1 0.0935 0.0685 0.1449 11.00000 0.05 0.28 Q6 1 0.7857 0.1699 0.7232 11.00000 0.05 0.27 Q7 1 0.1801 0.0454 0.2151 11.00000 0.05 0.27 Q8 1 0.9948 0.1867 0.4629 11.00000 0.05 0.27 Q9 1 0.0714 0.1293 0.1560 11.00000 0.05 0.27 Q10 1 0.5027 0.0199 0.3745 11.00000 0.05 0.26 Q11 1 0.4612 0.0736 0.3859 11.00000 0.05 0.26 Q12 1 1.0676 0.1034 0.5108 11.00000 0.05 0.26 Q13 1 0.3186 0.1919 0.2868 11.00000 0.05 0.26 Q14 1 0.0064 0.1706 0.1540 11.00000 0.05 0.26 Q15 1 0.7106 0.1719 0.2616 11.00000 0.05 0.26 ; 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 0.02867(11) 0.05005(4) 0.08791(6) 0.0256(3) Uani 1 1 d . . . C1 C -0.0529(4) 0.11357(16) 0.0777(2) 0.0215(10) Uani 1 1 d . . . C2 C 0.0079(4) 0.14747(16) 0.1408(2) 0.0222(10) Uani 1 1 d . . . H2 H -0.0227 0.1833 0.1455 0.027 Uiso 1 1 calc R . . C3 C 0.1170(4) 0.12133(16) 0.1941(2) 0.0218(10) Uani 1 1 d . . . S2 S 0.23457(12) 0.13926(4) 0.28095(6) 0.0255(3) Uani 1 1 d . . . C4 C 0.3235(4) 0.07593(16) 0.2903(2) 0.0224(10) Uani 1 1 d . . . C5 C 0.2614(4) 0.04318(17) 0.2264(2) 0.0221(9) Uani 1 1 d . . . H5 H 0.2949 0.0078 0.2204 0.027 Uiso 1 1 calc R . . C6 C 0.1480(4) 0.06792(16) 0.1743(2) 0.0209(9) Uani 1 1 d . . . C7 C -0.1620(4) 0.12667(17) 0.0115(2) 0.0231(10) Uani 1 1 d . . . C8 C -0.2105(4) 0.08901(17) -0.0483(2) 0.0230(10) Uani 1 1 d . . . N1 N -0.2457(4) 0.05807(15) -0.0961(2) 0.0356(10) Uani 1 1 d . . . C9 C -0.2200(4) 0.17961(19) 0.0005(2) 0.0250(10) Uani 1 1 d . . . N2 N -0.2620(4) 0.22240(16) -0.0079(2) 0.0408(10) Uani 1 1 d . . . C10 C 0.4362(4) 0.05830(17) 0.3509(2) 0.0224(10) Uani 1 1 d . . . H10 H 0.4714 0.0232 0.3438 0.027 Uiso 1 1 calc R . . C11 C 0.5103(4) 0.08237(17) 0.4221(2) 0.0217(10) Uani 1 1 d . . . C12 C 0.4917(4) 0.13519(17) 0.4445(2) 0.0257(10) Uani 1 1 d . . . H12 H 0.4295 0.1584 0.4091 0.031 Uiso 1 1 calc R . . C13 C 0.5606(4) 0.15419(17) 0.5157(2) 0.0272(10) Uani 1 1 d . . . H13 H 0.5490 0.1905 0.5278 0.033 Uiso 1 1 calc R . . C14 C 0.6494(4) 0.12043(17) 0.5718(2) 0.0232(10) Uani 1 1 d . . . C15 C 0.6728(4) 0.06801(17) 0.5483(2) 0.0251(10) Uani 1 1 d . . . H15 H 0.7347 0.0445 0.5834 0.030 Uiso 1 1 calc R . . C16 C 0.6079(4) 0.05062(17) 0.4761(2) 0.0243(10) Uani 1 1 d . . . H16 H 0.6295 0.0154 0.4614 0.029 Uiso 1 1 calc R . . N3 N 0.7085(4) 0.13809(14) 0.64534(19) 0.0273(9) Uani 1 1 d . . . C17 C 0.7127(5) 0.19353(17) 0.6684(2) 0.0348(11) Uani 1 1 d . . . H17A H 0.7214 0.2155 0.6215 0.042 Uiso 1 1 calc R . . H17B H 0.8100 0.1998 0.7065 0.042 Uiso 1 1 calc R . . C18 C 0.5676(5) 0.2110(2) 0.7047(3) 0.0531(14) Uani 1 1 d . . . H18A H 0.5783 0.2484 0.7189 0.080 Uiso 1 1 calc R . . H18B H 0.5592 0.1900 0.7519 0.080 Uiso 1 1 calc R . . H18C H 0.4707 0.2059 0.6668 0.080 Uiso 1 1 calc R . . C19 C 0.7501(4) 0.10009(17) 0.7098(2) 0.0296(11) Uani 1 1 d . . . H19A H 0.6881 0.0672 0.6976 0.035 Uiso 1 1 calc R . . H19B H 0.7181 0.1150 0.7588 0.035 Uiso 1 1 calc R . . C20 C 0.9276(4) 0.08687(18) 0.7234(2) 0.0369(12) Uani 1 1 d . . . H20A H 0.9482 0.0614 0.7666 0.055 Uiso 1 1 calc R . . H20B H 0.9896 0.1191 0.7369 0.055 Uiso 1 1 calc R . . H20C H 0.9597 0.0715 0.6755 0.055 Uiso 1 1 calc R . . S3 S 1.09898(12) 0.06237(5) 0.48391(7) 0.0314(3) Uani 1 1 d . . . C21 C 1.0828(4) 0.12657(17) 0.5214(2) 0.0275(10) Uani 1 1 d . . . C22 C 0.9751(4) 0.15863(17) 0.4710(2) 0.0224(10) Uani 1 1 d . . . H22 H 0.9487 0.1941 0.4818 0.027 Uiso 1 1 calc R . . C23 C 0.9143(4) 0.13118(17) 0.4046(2) 0.0250(10) Uani 1 1 d . . . S4 S 0.78450(12) 0.14716(5) 0.32079(7) 0.0292(3) Uani 1 1 d . . . C24 C 0.7942(4) 0.08229(17) 0.2847(2) 0.0265(10) Uani 1 1 d . . . C25 C 0.9014(4) 0.05043(18) 0.3367(2) 0.0275(10) Uani 1 1 d . . . H25 H 0.9248 0.0145 0.3271 0.033 Uiso 1 1 calc R . . C26 C 0.9657(4) 0.07768(17) 0.4014(2) 0.0265(10) Uani 1 1 d . . . C27 C 1.1707(4) 0.13884(17) 0.5935(2) 0.0264(10) Uani 1 1 d . . . C28 C 1.2735(5) 0.10004(18) 0.6339(2) 0.0257(10) Uani 1 1 d . . . N4 N 1.3525(4) 0.06696(15) 0.6639(2) 0.0356(10) Uani 1 1 d . . . C29 C 1.1514(5) 0.1881(2) 0.6302(3) 0.0330(11) Uani 1 1 d . . . N5 N 1.1337(5) 0.22793(17) 0.6606(2) 0.0511(12) Uani 1 1 d . . . C30 C 0.7107(4) 0.06233(17) 0.2163(2) 0.0254(10) Uani 1 1 d . . . H30 H 0.7322 0.0262 0.2074 0.030 Uiso 1 1 calc R . . C31 C 0.5986(4) 0.08557(17) 0.1565(2) 0.0252(10) Uani 1 1 d . . . C32 C 0.5491(5) 0.13871(17) 0.1536(2) 0.0303(11) Uani 1 1 d . . . H32 H 0.5946 0.1622 0.1937 0.036 Uiso 1 1 calc R . . C33 C 0.4374(5) 0.15775(17) 0.0947(2) 0.0283(10) Uani 1 1 d . . . H33 H 0.4081 0.1940 0.0949 0.034 Uiso 1 1 calc R . . C34 C 0.3646(4) 0.12443(17) 0.0336(2) 0.0244(10) Uani 1 1 d . . . C35 C 0.4164(4) 0.07158(17) 0.0357(2) 0.0266(10) Uani 1 1 d . . . H35 H 0.3738 0.0484 -0.0054 0.032 Uiso 1 1 calc R . . C36 C 0.5265(4) 0.05244(18) 0.0952(2) 0.0295(11) Uani 1 1 d . . . H36 H 0.5550 0.0162 0.0954 0.035 Uiso 1 1 calc R . . N6 N 0.2507(4) 0.14300(14) -0.02396(19) 0.0271(9) Uani 1 1 d . . . C37 C 0.1936(5) 0.19758(17) -0.0257(3) 0.0330(11) Uani 1 1 d . . . H37A H 0.1982 0.2104 0.0290 0.040 Uiso 1 1 calc R . . H37B H 0.0797 0.1982 -0.0497 0.040 Uiso 1 1 calc R . . C38 C 0.2876(5) 0.23497(19) -0.0705(3) 0.0485(14) Uani 1 1 d . . . H38A H 0.2424 0.2706 -0.0689 0.073 Uiso 1 1 calc R . . H38B H 0.2813 0.2233 -0.1252 0.073 Uiso 1 1 calc R . . H38C H 0.4001 0.2354 -0.0465 0.073 Uiso 1 1 calc R . . C39 C 0.1939(5) 0.10975(19) -0.0917(2) 0.0345(12) Uani 1 1 d . . . H39A H 0.0936 0.1251 -0.1194 0.041 Uiso 1 1 calc R . . H39B H 0.1679 0.0743 -0.0727 0.041 Uiso 1 1 calc R . . C40 C 0.3145(5) 0.1039(2) -0.1498(2) 0.0433(13) Uani 1 1 d . . . H40A H 0.2689 0.0813 -0.1935 0.065 Uiso 1 1 calc R . . H40B H 0.4132 0.0877 -0.1233 0.065 Uiso 1 1 calc R . . H40C H 0.3391 0.1387 -0.1699 0.065 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 0.0261(5) 0.0274(7) 0.0226(6) -0.0022(5) 0.0012(4) 0.0002(5) C1 0.018(2) 0.026(3) 0.021(2) 0.0001(18) 0.0078(17) -0.0055(19) C2 0.018(2) 0.023(3) 0.027(3) 0.0003(19) 0.0082(18) -0.0001(18) C3 0.019(2) 0.026(3) 0.022(3) -0.0003(19) 0.0105(17) -0.0044(19) S2 0.0267(5) 0.0276(7) 0.0218(6) -0.0027(5) 0.0015(4) 0.0009(5) C4 0.021(2) 0.026(3) 0.022(3) -0.0049(19) 0.0089(18) -0.0027(19) C5 0.021(2) 0.026(3) 0.021(2) -0.0003(19) 0.0075(17) 0.0006(19) C6 0.020(2) 0.022(3) 0.022(3) -0.0025(18) 0.0063(17) -0.0014(19) C7 0.017(2) 0.033(3) 0.020(2) 0.0012(19) 0.0046(17) 0.0041(19) C8 0.020(2) 0.027(3) 0.022(3) 0.006(2) 0.0034(18) 0.001(2) N1 0.037(2) 0.035(3) 0.033(3) -0.0057(19) -0.0021(18) 0.0012(19) C9 0.019(2) 0.037(3) 0.019(3) 0.002(2) 0.0017(18) -0.002(2) N2 0.040(2) 0.037(3) 0.046(3) 0.005(2) 0.0037(19) 0.009(2) C10 0.021(2) 0.027(3) 0.022(3) 0.0022(19) 0.0127(18) -0.0028(19) C11 0.018(2) 0.027(3) 0.020(3) -0.0011(19) 0.0049(17) -0.0012(19) C12 0.021(2) 0.026(3) 0.030(3) 0.005(2) 0.0033(18) 0.000(2) C13 0.028(2) 0.029(3) 0.025(3) 0.000(2) 0.0021(19) 0.002(2) C14 0.017(2) 0.035(3) 0.019(3) 0.0004(19) 0.0036(17) -0.003(2) C15 0.023(2) 0.030(3) 0.022(3) 0.007(2) 0.0015(18) 0.003(2) C16 0.019(2) 0.026(3) 0.030(3) -0.001(2) 0.0082(18) -0.0003(19) N3 0.0319(19) 0.027(2) 0.021(2) 0.0034(16) -0.0021(16) 0.0025(17) C17 0.046(3) 0.033(3) 0.023(3) 0.003(2) -0.003(2) -0.005(2) C18 0.060(3) 0.040(3) 0.062(4) 0.000(3) 0.020(3) 0.004(3) C19 0.031(2) 0.038(3) 0.020(3) 0.006(2) 0.0050(19) 0.000(2) C20 0.034(2) 0.044(3) 0.031(3) 0.004(2) -0.003(2) -0.001(2) S3 0.0268(6) 0.0329(7) 0.0335(7) -0.0001(5) 0.0008(5) 0.0049(5) C21 0.024(2) 0.030(3) 0.030(3) 0.003(2) 0.0114(19) -0.003(2) C22 0.0169(19) 0.030(3) 0.022(3) 0.0064(19) 0.0061(17) -0.0009(19) C23 0.017(2) 0.031(3) 0.029(3) 0.005(2) 0.0097(18) 0.0009(19) S4 0.0269(6) 0.0313(7) 0.0293(7) 0.0011(5) 0.0038(5) 0.0020(5) C24 0.022(2) 0.027(3) 0.032(3) -0.002(2) 0.0112(19) 0.000(2) C25 0.025(2) 0.028(3) 0.030(3) 0.000(2) 0.0091(19) -0.007(2) C26 0.021(2) 0.026(3) 0.034(3) 0.003(2) 0.0110(19) 0.003(2) C27 0.022(2) 0.031(3) 0.026(3) -0.003(2) 0.0054(18) -0.005(2) C28 0.022(2) 0.036(3) 0.019(3) 0.001(2) 0.0066(18) 0.000(2) N4 0.032(2) 0.040(3) 0.034(3) -0.0014(19) 0.0013(17) 0.0056(19) C29 0.030(2) 0.039(3) 0.028(3) 0.002(2) -0.001(2) 0.001(2) N5 0.057(3) 0.039(3) 0.054(3) -0.005(2) -0.006(2) 0.007(2) C30 0.022(2) 0.025(3) 0.031(3) 0.000(2) 0.0122(19) -0.0010(19) C31 0.026(2) 0.027(3) 0.025(3) 0.003(2) 0.0119(19) 0.001(2) C32 0.032(2) 0.030(3) 0.029(3) -0.004(2) 0.003(2) -0.001(2) C33 0.036(2) 0.025(3) 0.024(3) -0.002(2) 0.006(2) 0.005(2) C34 0.021(2) 0.033(3) 0.022(3) 0.000(2) 0.0113(18) -0.001(2) C35 0.030(2) 0.033(3) 0.018(3) -0.0077(19) 0.0053(18) -0.001(2) C36 0.034(2) 0.029(3) 0.027(3) -0.004(2) 0.012(2) 0.004(2) N6 0.0271(19) 0.031(2) 0.023(2) -0.0010(16) 0.0025(16) -0.0004(17) C37 0.026(2) 0.036(3) 0.037(3) 0.004(2) 0.003(2) 0.003(2) C38 0.039(3) 0.035(3) 0.075(4) 0.009(3) 0.017(3) -0.005(2) C39 0.032(2) 0.047(3) 0.024(3) -0.002(2) 0.000(2) -0.002(2) C40 0.047(3) 0.058(4) 0.026(3) -0.003(2) 0.008(2) 0.002(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 C6 1.737(4) . ? S1 C1 1.749(4) . ? C1 C7 1.401(5) . ? C1 C2 1.423(5) . ? C2 C3 1.376(5) . ? C2 H2 0.9500 . ? C3 C6 1.427(5) . ? C3 S2 1.737(4) . ? S2 C4 1.768(4) . ? C4 C10 1.384(5) . ? C4 C5 1.419(5) . ? C5 C6 1.368(5) . ? C5 H5 0.9500 . ? C7 C8 1.422(6) . ? C7 C9 1.431(6) . ? C8 N1 1.145(5) . ? C9 N2 1.143(5) . ? C10 C11 1.434(5) . ? C10 H10 0.9500 . ? C11 C16 1.405(5) . ? C11 C12 1.406(5) . ? C12 C13 1.369(5) . ? C12 H12 0.9500 . ? C13 C14 1.423(5) . ? C13 H13 0.9500 . ? C14 N3 1.369(5) . ? C14 C15 1.409(5) . ? C15 C16 1.361(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N3 C17 1.459(5) . ? N3 C19 1.474(5) . ? C17 C18 1.506(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.516(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? S3 C26 1.729(4) . ? S3 C21 1.761(4) . ? C21 C27 1.390(5) . ? C21 C22 1.421(5) . ? C22 C23 1.375(5) . ? C22 H22 0.9500 . ? C23 C26 1.426(6) . ? C23 S4 1.735(4) . ? S4 C24 1.762(4) . ? C24 C30 1.381(5) . ? C24 C25 1.431(5) . ? C25 C26 1.358(5) . ? C25 H25 0.9500 . ? C27 C29 1.417(6) . ? C27 C28 1.427(6) . ? C28 N4 1.147(5) . ? C29 N5 1.155(6) . ? C30 C31 1.426(5) . ? C30 H30 0.9500 . ? C31 C32 1.408(6) . ? C31 C36 1.417(5) . ? C32 C33 1.372(5) . ? C32 H32 0.9500 . ? C33 C34 1.421(5) . ? C33 H33 0.9500 . ? C34 N6 1.365(5) . ? C34 C35 1.406(5) . ? C35 C36 1.373(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? N6 C37 1.462(5) . ? N6 C39 1.464(5) . ? C37 C38 1.507(6) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.519(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? 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 C6 S1 C1 91.16(19) . . ? C7 C1 C2 127.2(4) . . ? C7 C1 S1 120.3(3) . . ? C2 C1 S1 112.5(3) . . ? C3 C2 C1 110.9(4) . . ? C3 C2 H2 124.6 . . ? C1 C2 H2 124.6 . . ? C2 C3 C6 115.1(4) . . ? C2 C3 S2 134.3(3) . . ? C6 C3 S2 110.6(3) . . ? C3 S2 C4 91.49(19) . . ? C10 C4 C5 122.5(4) . . ? C10 C4 S2 126.8(3) . . ? C5 C4 S2 110.6(3) . . ? C6 C5 C4 113.0(4) . . ? C6 C5 H5 123.5 . . ? C4 C5 H5 123.5 . . ? C5 C6 C3 114.3(4) . . ? C5 C6 S1 135.4(3) . . ? C3 C6 S1 110.3(3) . . ? C1 C7 C8 121.4(4) . . ? C1 C7 C9 120.2(4) . . ? C8 C7 C9 118.3(3) . . ? N1 C8 C7 178.2(4) . . ? N2 C9 C7 178.1(4) . . ? C4 C10 C11 132.9(4) . . ? C4 C10 H10 113.6 . . ? C11 C10 H10 113.6 . . ? C16 C11 C12 116.2(4) . . ? C16 C11 C10 117.9(4) . . ? C12 C11 C10 125.9(4) . . ? C13 C12 C11 121.9(4) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? N3 C14 C15 121.6(4) . . ? N3 C14 C13 121.4(4) . . ? C15 C14 C13 116.9(4) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C11 122.9(4) . . ? C15 C16 H16 118.5 . . ? C11 C16 H16 118.5 . . ? C14 N3 C17 123.9(3) . . ? C14 N3 C19 120.0(4) . . ? C17 N3 C19 115.5(3) . . ? N3 C17 C18 113.8(4) . . ? N3 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N3 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C20 113.0(3) . . ? N3 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? N3 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 S3 C21 91.1(2) . . ? C27 C21 C22 129.4(4) . . ? C27 C21 S3 118.3(3) . . ? C22 C21 S3 112.3(3) . . ? C23 C22 C21 110.6(4) . . ? C23 C22 H22 124.7 . . ? C21 C22 H22 124.7 . . ? C22 C23 C26 115.6(4) . . ? C22 C23 S4 133.9(3) . . ? C26 C23 S4 110.5(3) . . ? C23 S4 C24 91.2(2) . . ? C30 C24 C25 122.1(4) . . ? C30 C24 S4 126.8(3) . . ? C25 C24 S4 111.2(3) . . ? C26 C25 C24 111.9(4) . . ? C26 C25 H25 124.0 . . ? C24 C25 H25 124.0 . . ? C25 C26 C23 115.2(4) . . ? C25 C26 S3 134.4(4) . . ? C23 C26 S3 110.4(3) . . ? C21 C27 C29 121.0(4) . . ? C21 C27 C28 119.7(4) . . ? C29 C27 C28 119.2(4) . . ? N4 C28 C27 176.5(5) . . ? N5 C29 C27 178.9(5) . . ? C24 C30 C31 132.4(4) . . ? C24 C30 H30 113.8 . . ? C31 C30 H30 113.8 . . ? C32 C31 C36 116.4(4) . . ? C32 C31 C30 125.7(4) . . ? C36 C31 C30 117.8(4) . . ? C33 C32 C31 122.1(4) . . ? C33 C32 H32 118.9 . . ? C31 C32 H32 118.9 . . ? C32 C33 C34 121.4(4) . . ? C32 C33 H33 119.3 . . ? C34 C33 H33 119.3 . . ? N6 C34 C35 122.1(4) . . ? N6 C34 C33 121.5(4) . . ? C35 C34 C33 116.4(4) . . ? C36 C35 C34 122.0(4) . . ? C36 C35 H35 119.0 . . ? C34 C35 H35 119.0 . . ? C35 C36 C31 121.5(4) . . ? C35 C36 H36 119.2 . . ? C31 C36 H36 119.2 . . ? C34 N6 C37 122.5(3) . . ? C34 N6 C39 120.0(4) . . ? C37 N6 C39 117.1(3) . . ? N6 C37 C38 114.4(3) . . ? N6 C37 H37A 108.7 . . ? C38 C37 H37A 108.7 . . ? N6 C37 H37B 108.7 . . ? C38 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N6 C39 C40 113.7(3) . . ? N6 C39 H39A 108.8 . . ? C40 C39 H39A 108.8 . . ? N6 C39 H39B 108.8 . . ? C40 C39 H39B 108.8 . . ? H39A C39 H39B 107.7 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? 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 C6 S1 C1 C7 176.9(3) . . . . ? C6 S1 C1 C2 -1.5(3) . . . . ? C7 C1 C2 C3 -178.0(4) . . . . ? S1 C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C6 1.5(5) . . . . ? C1 C2 C3 S2 178.9(3) . . . . ? C2 C3 S2 C4 -177.5(4) . . . . ? C6 C3 S2 C4 0.0(3) . . . . ? C3 S2 C4 C10 -178.4(3) . . . . ? C3 S2 C4 C5 0.4(3) . . . . ? C10 C4 C5 C6 178.1(3) . . . . ? S2 C4 C5 C6 -0.7(4) . . . . ? C4 C5 C6 C3 0.8(5) . . . . ? C4 C5 C6 S1 -179.0(3) . . . . ? C2 C3 C6 C5 177.6(3) . . . . ? S2 C3 C6 C5 -0.4(4) . . . . ? C2 C3 C6 S1 -2.6(4) . . . . ? S2 C3 C6 S1 179.42(18) . . . . ? C1 S1 C6 C5 -178.0(4) . . . . ? C1 S1 C6 C3 2.2(3) . . . . ? C2 C1 C7 C8 178.7(4) . . . . ? S1 C1 C7 C8 0.5(5) . . . . ? C2 C1 C7 C9 2.5(6) . . . . ? S1 C1 C7 C9 -175.6(3) . . . . ? C5 C4 C10 C11 -176.7(4) . . . . ? S2 C4 C10 C11 2.0(6) . . . . ? C4 C10 C11 C16 172.6(4) . . . . ? C4 C10 C11 C12 -5.8(7) . . . . ? C16 C11 C12 C13 -2.0(6) . . . . ? C10 C11 C12 C13 176.5(4) . . . . ? C11 C12 C13 C14 -2.6(6) . . . . ? C12 C13 C14 N3 -175.0(4) . . . . ? C12 C13 C14 C15 4.6(5) . . . . ? N3 C14 C15 C16 177.4(3) . . . . ? C13 C14 C15 C16 -2.2(5) . . . . ? C14 C15 C16 C11 -2.4(6) . . . . ? C12 C11 C16 C15 4.5(6) . . . . ? C10 C11 C16 C15 -174.2(3) . . . . ? C15 C14 N3 C17 168.9(4) . . . . ? C13 C14 N3 C17 -11.5(6) . . . . ? C15 C14 N3 C19 -20.4(5) . . . . ? C13 C14 N3 C19 159.3(3) . . . . ? C14 N3 C17 C18 92.8(5) . . . . ? C19 N3 C17 C18 -78.3(4) . . . . ? C14 N3 C19 C20 97.5(4) . . . . ? C17 N3 C19 C20 -91.1(4) . . . . ? C26 S3 C21 C27 179.7(3) . . . . ? C26 S3 C21 C22 0.6(3) . . . . ? C27 C21 C22 C23 179.5(4) . . . . ? S3 C21 C22 C23 -1.5(4) . . . . ? C21 C22 C23 C26 2.0(5) . . . . ? C21 C22 C23 S4 -178.1(3) . . . . ? C22 C23 S4 C24 -177.8(4) . . . . ? C26 C23 S4 C24 2.1(3) . . . . ? C23 S4 C24 C30 177.1(4) . . . . ? C23 S4 C24 C25 -2.0(3) . . . . ? C30 C24 C25 C26 -177.8(4) . . . . ? S4 C24 C25 C26 1.4(4) . . . . ? C24 C25 C26 C23 0.2(5) . . . . ? C24 C25 C26 S3 179.9(3) . . . . ? C22 C23 C26 C25 178.2(3) . . . . ? S4 C23 C26 C25 -1.8(4) . . . . ? C22 C23 C26 S3 -1.6(4) . . . . ? S4 C23 C26 S3 178.47(19) . . . . ? C21 S3 C26 C25 -179.2(4) . . . . ? C21 S3 C26 C23 0.5(3) . . . . ? C22 C21 C27 C29 4.9(7) . . . . ? S3 C21 C27 C29 -174.1(3) . . . . ? C22 C21 C27 C28 -179.5(4) . . . . ? S3 C21 C27 C28 1.5(5) . . . . ? C25 C24 C30 C31 179.5(4) . . . . ? S4 C24 C30 C31 0.4(6) . . . . ? C24 C30 C31 C32 2.1(7) . . . . ? C24 C30 C31 C36 -176.2(4) . . . . ? C36 C31 C32 C33 -0.1(6) . . . . ? C30 C31 C32 C33 -178.4(4) . . . . ? C31 C32 C33 C34 0.4(6) . . . . ? C32 C33 C34 N6 178.4(4) . . . . ? C32 C33 C34 C35 -1.6(6) . . . . ? N6 C34 C35 C36 -177.4(4) . . . . ? C33 C34 C35 C36 2.6(6) . . . . ? C34 C35 C36 C31 -2.4(6) . . . . ? C32 C31 C36 C35 1.0(6) . . . . ? C30 C31 C36 C35 179.5(3) . . . . ? C35 C34 N6 C37 178.7(3) . . . . ? C33 C34 N6 C37 -1.3(6) . . . . ? C35 C34 N6 C39 -8.2(5) . . . . ? C33 C34 N6 C39 171.8(3) . . . . ? C34 N6 C37 C38 90.0(5) . . . . ? C39 N6 C37 C38 -83.3(5) . . . . ? C34 N6 C39 C40 -73.5(5) . . . . ? C37 N6 C39 C40 100.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 N5 0.95 2.60 3.332(6) 134.1 4_465 C12 H12 S2 0.95 2.61 3.309(4) 130.9 . C32 H32 S4 0.95 2.56 3.270(4) 132.2 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.327 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 943683'