# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year 2011 _journal_volume 2 _journal_page_first 0 _publ_contact_author_email ddsouza1@staffmail.ed.ac.uk _publ_contact_author_name "Daniel M. D'Souza" loop_ _publ_author_name 'David A. Leigh' 'Andrea Altieri' 'Vincent Aucagne' 'Romen Carrillo' G.Clarkson D.D'Souza J.Dunnett K.Mullen data_jadfi _database_code_depnum_ccdc_archive 'CCDC 828037' #TrackingRef '- sufiderot6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C64 H59 N5 O7 S.C H4 O' _chemical_formula_sum 'C65 H62 N5 O8 S' _chemical_formula_weight 1073.26 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.7400(2) _cell_length_b 13.8252(3) _cell_length_c 16.4187(4) _cell_angle_alpha 97.0850(10) _cell_angle_beta 97.75 _cell_angle_gamma 98.6950(10) _cell_volume 2801.86(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.875 _cell_measurement_theta_max 28.44 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1134 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 SMART _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 16902 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.1487 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.44 _reflns_number_total 12333 _reflns_number_gt 4981 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART/SAINT _computing_data_reduction SMART _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0889P)^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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12333 _refine_ls_number_parameters 712 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1862 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.2115 _refine_ls_wR_factor_gt 0.1648 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.160 _refine_ls_shift/su_mean 0.010 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 C1 C 1.0395(3) 0.5180(3) 0.1524(2) 0.0388(10) Uani 1 1 d . . . H1B H 1.0092 0.4467 0.1368 0.047 Uiso 1 1 calc R . . H1A H 1.1148 0.5280 0.1418 0.047 Uiso 1 1 calc R . . N2 N 1.0375(2) 0.5479(2) 0.24138(18) 0.0389(8) Uani 1 1 d . . . H2 H 0.9820 0.5226 0.2631 0.047 Uiso 1 1 calc R . . C3 C 1.1168(3) 0.6121(3) 0.2904(2) 0.0439(10) Uani 1 1 d . . . O3 O 1.2003(2) 0.6461(2) 0.26561(18) 0.0601(9) Uani 1 1 d . . . C4 C 1.1000(3) 0.6458(3) 0.3776(2) 0.0473(11) Uani 1 1 d . . . C5 C 1.0125(3) 0.6051(3) 0.4119(2) 0.0436(10) Uani 1 1 d . . . H5 H 0.9603 0.5534 0.3796 0.052 Uiso 1 1 calc R . . C6 C 1.0005(3) 0.6390(3) 0.4928(2) 0.0522(12) Uani 1 1 d . . . C7 C 1.0796(5) 0.7131(5) 0.5384(3) 0.101(2) Uani 1 1 d . . . H7 H 1.0738 0.7367 0.5942 0.121 Uiso 1 1 calc R . . C8 C 1.1673(6) 0.7538(6) 0.5041(4) 0.137(3) Uani 1 1 d . . . H8 H 1.2209 0.8044 0.5364 0.165 Uiso 1 1 calc R . . C9 C 1.1759(5) 0.7204(4) 0.4238(3) 0.095(2) Uani 1 1 d . . . H9 H 1.2348 0.7491 0.3999 0.115 Uiso 1 1 calc R . . C10 C 0.9058(4) 0.6029(4) 0.5321(3) 0.0540(12) Uani 1 1 d . . . O10 O 0.9054(3) 0.6213(3) 0.60695(17) 0.0708(10) Uani 1 1 d . . . N11 N 0.8202(3) 0.5493(3) 0.4805(2) 0.0632(11) Uani 1 1 d . . . H11 H 0.8225 0.5377 0.4270 0.076 Uiso 1 1 calc R . . C12 C 0.7230(4) 0.5099(6) 0.5126(3) 0.104(2) Uani 1 1 d . . . H12B H 0.7127 0.5568 0.5604 0.124 Uiso 1 1 calc R . . H12A H 0.7317 0.4464 0.5325 0.124 Uiso 1 1 calc R . . C13 C 0.6249(4) 0.4937(6) 0.4460(3) 0.0722(17) Uani 1 1 d . . . C14 C 0.5843(5) 0.4019(5) 0.4023(3) 0.0796(17) Uani 1 1 d . . . H14 H 0.6179 0.3475 0.4148 0.095 Uiso 1 1 calc R . . C15 C 0.4950(4) 0.3859(4) 0.3398(3) 0.0682(14) Uani 1 1 d . . . H15 H 0.4688 0.3213 0.3102 0.082 Uiso 1 1 calc R . . C16 C 0.4448(3) 0.4635(3) 0.3210(2) 0.0439(11) Uani 1 1 d . . . C17 C 0.4850(4) 0.5561(4) 0.3652(3) 0.0586(13) Uani 1 1 d . . . H17 H 0.4516 0.6107 0.3532 0.070 Uiso 1 1 calc R . . C18 C 0.5738(4) 0.5701(5) 0.4271(3) 0.0760(17) Uani 1 1 d . . . H18 H 0.5998 0.6345 0.4571 0.091 Uiso 1 1 calc R . . C19 C 0.3472(3) 0.4473(3) 0.2531(2) 0.0498(12) Uani 1 1 d . . . H19B H 0.3460 0.3849 0.2159 0.060 Uiso 1 1 calc R . . H19A H 0.2812 0.4398 0.2790 0.060 Uiso 1 1 calc R . . N20 N 0.3457(2) 0.5277(2) 0.20329(18) 0.0431(9) Uani 1 1 d . . . H20 H 0.3035 0.5714 0.2124 0.052 Uiso 1 1 calc R . . C21 C 0.4078(3) 0.5360(3) 0.1440(2) 0.0339(9) Uani 1 1 d . . . O21 O 0.4672(2) 0.47604(19) 0.12832(15) 0.0391(6) Uani 1 1 d . . . C22 C 0.4025(3) 0.6215(3) 0.0967(2) 0.0316(9) Uani 1 1 d . . . C23 C 0.4841(3) 0.6429(3) 0.0497(2) 0.0314(9) Uani 1 1 d . . . H23 H 0.5392 0.6037 0.0494 0.038 Uiso 1 1 calc R . . C24 C 0.4863(3) 0.7207(3) 0.0031(2) 0.0341(9) Uani 1 1 d . . . C25 C 0.4026(3) 0.7746(3) 0.0015(2) 0.0399(10) Uani 1 1 d . . . H25 H 0.4019 0.8267 -0.0311 0.048 Uiso 1 1 calc R . . C26 C 0.3203(3) 0.7534(3) 0.0468(2) 0.0465(11) Uani 1 1 d . . . H26 H 0.2633 0.7905 0.0449 0.056 Uiso 1 1 calc R . . C27 C 0.3208(3) 0.6784(3) 0.0948(2) 0.0412(10) Uani 1 1 d . . . H27 H 0.2650 0.6652 0.1269 0.049 Uiso 1 1 calc R . . C28 C 0.5769(3) 0.7451(3) -0.0436(2) 0.0347(9) Uani 1 1 d . . . O28 O 0.5647(2) 0.7656(2) -0.11481(15) 0.0442(7) Uani 1 1 d . . . N29 N 0.6735(2) 0.7415(2) -0.00031(18) 0.0357(8) Uani 1 1 d . . . H29 H 0.6756 0.7334 0.0522 0.043 Uiso 1 1 calc R . . C30 C 0.7743(3) 0.7497(3) -0.0327(2) 0.0423(10) Uani 1 1 d . . . H30B H 0.8093 0.8200 -0.0243 0.051 Uiso 1 1 calc R . . H30A H 0.7606 0.7253 -0.0931 0.051 Uiso 1 1 calc R . . C31 C 0.8477(3) 0.6899(3) 0.0113(2) 0.0343(9) Uani 1 1 d . . . C32 C 0.8141(3) 0.5897(3) 0.0097(2) 0.0413(10) Uani 1 1 d . . . H32 H 0.7468 0.5588 -0.0220 0.050 Uiso 1 1 calc R . . C33 C 0.8764(3) 0.5339(3) 0.0531(2) 0.0367(10) Uani 1 1 d . . . H33 H 0.8515 0.4651 0.0510 0.044 Uiso 1 1 calc R . . C34 C 0.9754(3) 0.5773(3) 0.1001(2) 0.0326(9) Uani 1 1 d . . . C35 C 1.0100(3) 0.6772(3) 0.1005(2) 0.0436(11) Uani 1 1 d . . . H35 H 1.0783 0.7079 0.1306 0.052 Uiso 1 1 calc R . . C36 C 0.9464(3) 0.7330(3) 0.0576(2) 0.0446(11) Uani 1 1 d . . . H36 H 0.9709 0.8018 0.0599 0.053 Uiso 1 1 calc R . . C37 C 0.6820(4) 0.8199(3) 0.3022(2) 0.0492(12) Uani 1 1 d . . . H37 H 0.6234 0.7624 0.3004 0.059 Uiso 1 1 calc R . . S38 S 0.75771(8) 0.78941(8) 0.21954(6) 0.0418(3) Uani 1 1 d . . . C39 C 0.7931(3) 0.6734(3) 0.2428(2) 0.0418(10) Uani 1 1 d . . . H39B H 0.8501 0.6572 0.2106 0.050 Uiso 1 1 calc R . . H39A H 0.8230 0.6808 0.3025 0.050 Uiso 1 1 calc R . . C40 C 0.6992(3) 0.5885(3) 0.2231(2) 0.0423(10) Uani 1 1 d . . . H40B H 0.6437 0.6028 0.2575 0.051 Uiso 1 1 calc R . . H40A H 0.6669 0.5829 0.1640 0.051 Uiso 1 1 calc R . . C41 C 0.7320(3) 0.4916(3) 0.2390(2) 0.0343(9) Uani 1 1 d . . . O41 O 0.8147(2) 0.48615(19) 0.28707(16) 0.0436(7) Uani 1 1 d . . . N42 N 0.6675(2) 0.4096(2) 0.19921(18) 0.0399(8) Uani 1 1 d . . . H42 H 0.6109 0.4136 0.1634 0.048 Uiso 1 1 calc R . . C43 C 0.6916(3) 0.3144(3) 0.2153(2) 0.0416(10) Uani 1 1 d . . . H43B H 0.6343 0.2618 0.1832 0.050 Uiso 1 1 calc R . . H43A H 0.6919 0.3099 0.2751 0.050 Uiso 1 1 calc R . . C44 C 0.7989(3) 0.2974(3) 0.1924(2) 0.0413(10) Uani 1 1 d . . . O44 O 0.8381(2) 0.3289(2) 0.13604(17) 0.0548(8) Uani 1 1 d . . . O45 O 0.8435(2) 0.23998(19) 0.24229(15) 0.0426(7) Uani 1 1 d . . . C46 C 0.9464(3) 0.2156(3) 0.2289(2) 0.0419(10) Uani 1 1 d . . . H46B H 1.0010 0.2424 0.2786 0.050 Uiso 1 1 calc R . . H46A H 0.9698 0.2447 0.1808 0.050 Uiso 1 1 calc R . . C47 C 0.9346(3) 0.1036(3) 0.2124(2) 0.0346(9) Uani 1 1 d . . . H47 H 0.8931 0.0774 0.2549 0.042 Uiso 1 1 calc R . . C48 C 0.8666(3) 0.0642(3) 0.1276(2) 0.0324(9) Uani 1 1 d . . . C49 C 0.7581(3) 0.0255(3) 0.1206(2) 0.0371(9) Uani 1 1 d . . . H49 H 0.7263 0.0219 0.1696 0.045 Uiso 1 1 calc R . . C50 C 0.6950(3) -0.0083(3) 0.0436(2) 0.0402(10) Uani 1 1 d . . . H50 H 0.6209 -0.0347 0.0400 0.048 Uiso 1 1 calc R . . C51 C 0.7406(3) -0.0032(3) -0.0273(2) 0.0395(10) Uani 1 1 d . . . H51 H 0.6982 -0.0268 -0.0802 0.047 Uiso 1 1 calc R . . C52 C 0.8483(3) 0.0363(3) -0.0219(2) 0.0403(10) Uani 1 1 d . . . H52 H 0.8797 0.0406 -0.0709 0.048 Uiso 1 1 calc R . . C53 C 0.9098(3) 0.0695(3) 0.0551(2) 0.0383(10) Uani 1 1 d . . . H53 H 0.9837 0.0965 0.0584 0.046 Uiso 1 1 calc R . . C54 C 1.0416(3) 0.0668(3) 0.2236(2) 0.0375(10) Uani 1 1 d . . . C55 C 1.1391(3) 0.1269(3) 0.2230(2) 0.0453(11) Uani 1 1 d . . . H55 H 1.1405 0.1934 0.2133 0.054 Uiso 1 1 calc R . . C56 C 1.2345(3) 0.0901(4) 0.2364(2) 0.0553(13) Uani 1 1 d . . . H56 H 1.3008 0.1319 0.2358 0.066 Uiso 1 1 calc R . . C57 C 1.2345(4) -0.0059(4) 0.2505(2) 0.0589(13) Uani 1 1 d . . . H57 H 1.3003 -0.0302 0.2605 0.071 Uiso 1 1 calc R . . C58 C 1.1380(4) -0.0664(4) 0.2500(3) 0.0571(12) Uani 1 1 d . . . H58 H 1.1372 -0.1331 0.2589 0.069 Uiso 1 1 calc R . . C59 C 1.0422(3) -0.0307(3) 0.2365(2) 0.0464(11) Uani 1 1 d . . . H59 H 0.9762 -0.0733 0.2362 0.056 Uiso 1 1 calc R . . C60 C 0.6291(3) 0.9073(3) 0.2820(2) 0.0439(11) Uani 1 1 d . . . C61 C 0.5453(4) 0.8934(3) 0.2163(3) 0.0540(12) Uani 1 1 d . . . H61 H 0.5196 0.8288 0.1867 0.065 Uiso 1 1 calc R . . C62 C 0.4984(4) 0.9712(4) 0.1932(3) 0.0607(13) Uani 1 1 d . . . H62 H 0.4414 0.9597 0.1476 0.073 Uiso 1 1 calc R . . C63 C 0.5332(4) 1.0657(4) 0.2355(3) 0.0581(13) Uani 1 1 d . . . H63 H 0.5012 1.1195 0.2191 0.070 Uiso 1 1 calc R . . C64 C 0.6159(4) 1.0807(3) 0.3026(3) 0.0565(12) Uani 1 1 d . . . H64 H 0.6399 1.1450 0.3332 0.068 Uiso 1 1 calc R . . C65 C 0.6638(4) 1.0013(3) 0.3253(3) 0.0520(12) Uani 1 1 d . . . H65 H 0.7207 1.0122 0.3709 0.062 Uiso 1 1 calc R . . C66 C 0.7498(6) 0.8364(4) 0.3876(3) 0.0788(18) Uani 1 1 d . . . C67 C 0.6962(7) 0.8245(4) 0.4534(3) 0.129(3) Uani 1 1 d . . . H67 H 0.6201 0.8066 0.4424 0.154 Uiso 1 1 calc R . . C68 C 0.7454(13) 0.8366(8) 0.5331(5) 0.210(8) Uani 1 1 d . . . H68 H 0.7064 0.8240 0.5771 0.252 Uiso 1 1 calc R . . C69 C 0.8608(13) 0.8698(7) 0.5480(6) 0.208(8) Uani 1 1 d . . . H69 H 0.8976 0.8827 0.6036 0.249 Uiso 1 1 calc R . . C70 C 0.9209(9) 0.8837(5) 0.4814(5) 0.177(5) Uani 1 1 d . . . H70 H 0.9968 0.9032 0.4906 0.212 Uiso 1 1 calc R . . C71 C 0.8603(7) 0.8666(4) 0.4023(3) 0.112(3) Uani 1 1 d . . . H71 H 0.8964 0.8761 0.3562 0.135 Uiso 1 1 calc R . . O1S O 1.4311(4) 0.9575(5) 0.4612(3) 0.1385(19) Uani 1 1 d . . . C1S C 1.4410(5) 0.8651(6) 0.4761(5) 0.115(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.047(3) 0.033(2) 0.0027(19) 0.0067(18) 0.0117(19) N2 0.0354(19) 0.048(2) 0.0319(17) 0.0063(16) 0.0024(15) 0.0034(16) C3 0.039(3) 0.050(3) 0.041(2) 0.001(2) 0.001(2) 0.012(2) O3 0.0356(17) 0.078(2) 0.0605(19) -0.0077(17) 0.0134(15) -0.0016(16) C4 0.039(3) 0.063(3) 0.036(2) -0.003(2) -0.001(2) 0.009(2) C5 0.042(3) 0.053(3) 0.032(2) -0.003(2) -0.0051(19) 0.011(2) C6 0.050(3) 0.070(3) 0.034(2) 0.000(2) -0.003(2) 0.016(2) C7 0.112(5) 0.125(6) 0.041(3) -0.035(3) 0.012(3) -0.023(4) C8 0.123(6) 0.168(7) 0.075(4) -0.054(4) 0.031(4) -0.077(5) C9 0.091(4) 0.120(5) 0.048(3) -0.028(3) 0.016(3) -0.041(4) C10 0.062(3) 0.066(3) 0.036(3) 0.005(2) 0.005(2) 0.022(3) O10 0.087(2) 0.095(3) 0.0283(16) 0.0025(17) 0.0095(16) 0.015(2) N11 0.047(2) 0.113(3) 0.0309(19) 0.017(2) 0.0064(18) 0.011(2) C12 0.053(3) 0.207(7) 0.052(3) 0.049(4) 0.004(3) 0.006(4) C13 0.047(3) 0.139(6) 0.037(3) 0.034(3) 0.014(2) 0.010(4) C14 0.077(4) 0.130(6) 0.052(3) 0.030(4) 0.021(3) 0.058(4) C15 0.075(4) 0.078(4) 0.053(3) 0.006(3) 0.008(3) 0.022(3) C16 0.040(3) 0.060(3) 0.034(2) 0.016(2) 0.0150(19) 0.004(2) C17 0.060(3) 0.060(3) 0.051(3) 0.017(3) 0.003(2) -0.007(2) C18 0.070(4) 0.094(4) 0.051(3) 0.027(3) -0.008(3) -0.023(3) C19 0.043(3) 0.057(3) 0.047(2) 0.011(2) 0.012(2) -0.007(2) N20 0.036(2) 0.053(2) 0.0414(19) 0.0132(17) 0.0074(16) 0.0055(16) C21 0.028(2) 0.035(2) 0.032(2) -0.0009(18) 0.0007(17) -0.0028(18) O21 0.0411(16) 0.0348(16) 0.0438(15) 0.0097(13) 0.0114(13) 0.0067(13) C22 0.025(2) 0.035(2) 0.031(2) 0.0007(17) -0.0032(16) 0.0027(17) C23 0.026(2) 0.030(2) 0.036(2) 0.0028(17) -0.0013(17) 0.0057(16) C24 0.034(2) 0.036(2) 0.030(2) 0.0025(18) -0.0001(17) 0.0045(18) C25 0.043(3) 0.035(2) 0.039(2) 0.0071(19) -0.006(2) 0.009(2) C26 0.037(2) 0.050(3) 0.053(3) 0.005(2) 0.001(2) 0.015(2) C27 0.029(2) 0.045(3) 0.048(2) 0.007(2) 0.0061(19) 0.0052(19) C28 0.038(2) 0.028(2) 0.036(2) 0.0050(18) -0.0016(19) 0.0059(17) O28 0.0493(18) 0.0511(18) 0.0341(15) 0.0173(14) 0.0000(13) 0.0111(14) N29 0.0333(19) 0.044(2) 0.0308(17) 0.0119(15) 0.0052(15) 0.0049(15) C30 0.040(2) 0.048(3) 0.043(2) 0.015(2) 0.011(2) 0.007(2) C31 0.037(2) 0.038(2) 0.030(2) 0.0127(18) 0.0069(17) 0.0040(18) C32 0.042(2) 0.042(3) 0.034(2) 0.0037(19) -0.0073(19) 0.000(2) C33 0.044(2) 0.035(2) 0.028(2) 0.0003(18) 0.0020(18) 0.0030(19) C34 0.030(2) 0.043(3) 0.0260(19) 0.0046(18) 0.0059(17) 0.0085(18) C35 0.025(2) 0.051(3) 0.051(3) 0.012(2) -0.0010(19) -0.0037(19) C36 0.040(3) 0.039(3) 0.053(3) 0.015(2) 0.008(2) -0.006(2) C37 0.083(3) 0.033(2) 0.033(2) 0.0062(19) 0.020(2) 0.005(2) S38 0.0438(6) 0.0404(6) 0.0416(6) 0.0091(5) 0.0076(5) 0.0049(5) C39 0.038(2) 0.043(3) 0.043(2) 0.010(2) 0.0041(19) 0.0055(19) C40 0.040(2) 0.040(3) 0.045(2) 0.003(2) 0.0017(19) 0.0077(19) C41 0.033(2) 0.041(3) 0.028(2) 0.0031(18) 0.0055(18) 0.0032(19) O41 0.0390(17) 0.0436(17) 0.0430(16) 0.0032(13) -0.0045(14) 0.0033(13) N42 0.042(2) 0.038(2) 0.0363(18) 0.0071(16) -0.0041(16) 0.0039(16) C43 0.042(3) 0.037(2) 0.044(2) 0.004(2) 0.003(2) 0.0036(19) C44 0.048(3) 0.033(2) 0.037(2) -0.002(2) -0.002(2) 0.001(2) O44 0.060(2) 0.061(2) 0.0501(18) 0.0231(16) 0.0174(15) 0.0126(16) O45 0.0448(17) 0.0489(18) 0.0361(15) 0.0082(14) 0.0033(13) 0.0151(14) C46 0.033(2) 0.054(3) 0.036(2) 0.001(2) 0.0029(18) 0.006(2) C47 0.034(2) 0.043(2) 0.028(2) 0.0092(18) 0.0082(17) 0.0039(18) C48 0.035(2) 0.033(2) 0.031(2) 0.0084(17) 0.0069(17) 0.0066(17) C49 0.035(2) 0.043(2) 0.038(2) 0.0114(19) 0.0132(19) 0.0100(19) C50 0.034(2) 0.041(2) 0.044(2) 0.007(2) 0.004(2) 0.0027(18) C51 0.040(2) 0.042(2) 0.035(2) 0.0040(19) -0.0019(19) 0.0090(19) C52 0.045(3) 0.049(3) 0.030(2) 0.0100(19) 0.0097(19) 0.011(2) C53 0.034(2) 0.045(3) 0.036(2) 0.0086(19) 0.0068(18) 0.0017(18) C54 0.033(2) 0.056(3) 0.0238(19) 0.0069(19) 0.0047(17) 0.008(2) C55 0.040(3) 0.061(3) 0.034(2) 0.008(2) 0.0050(19) 0.004(2) C56 0.034(3) 0.087(4) 0.039(2) -0.002(3) 0.002(2) 0.002(3) C57 0.042(3) 0.097(4) 0.043(3) 0.009(3) 0.003(2) 0.031(3) C58 0.059(3) 0.066(3) 0.054(3) 0.018(3) 0.010(2) 0.026(3) C59 0.045(3) 0.056(3) 0.040(2) 0.016(2) 0.006(2) 0.008(2) C60 0.058(3) 0.034(3) 0.044(2) 0.007(2) 0.024(2) 0.005(2) C61 0.046(3) 0.046(3) 0.068(3) 0.000(2) 0.016(2) 0.004(2) C62 0.040(3) 0.061(3) 0.078(3) 0.000(3) 0.010(2) 0.008(2) C63 0.052(3) 0.055(3) 0.078(3) 0.024(3) 0.025(3) 0.020(2) C64 0.077(4) 0.039(3) 0.057(3) 0.005(2) 0.024(3) 0.012(2) C65 0.076(3) 0.041(3) 0.040(2) 0.010(2) 0.013(2) 0.009(2) C66 0.159(6) 0.041(3) 0.039(3) 0.007(2) 0.011(4) 0.028(3) C67 0.283(10) 0.081(5) 0.049(4) 0.026(3) 0.067(5) 0.064(5) C68 0.49(2) 0.111(9) 0.046(6) 0.018(5) 0.049(9) 0.104(12) C69 0.47(2) 0.074(6) 0.049(5) -0.011(4) -0.075(10) 0.078(10) C70 0.302(13) 0.098(6) 0.086(5) 0.004(5) -0.097(7) 0.013(7) C71 0.177(7) 0.079(5) 0.055(4) 0.004(3) -0.047(4) 0.002(5) O1S 0.151(5) 0.163(5) 0.104(3) -0.012(4) 0.051(3) 0.032(4) C1S 0.060(4) 0.102(5) 0.163(7) -0.019(5) 0.049(4) -0.042(4) _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 C1 N2 1.473(4) . ? C1 C34 1.505(5) . ? N2 C3 1.338(5) . ? C3 O3 1.237(5) . ? C3 C4 1.504(5) . ? C4 C9 1.372(6) . ? C4 C5 1.390(6) . ? C5 C6 1.389(5) . ? C6 C7 1.387(6) . ? C6 C10 1.492(6) . ? C7 C8 1.393(7) . ? C8 C9 1.366(7) . ? C10 O10 1.225(5) . ? C10 N11 1.344(5) . ? N11 C12 1.466(6) . ? C12 C13 1.515(6) . ? C13 C14 1.367(8) . ? C13 C18 1.367(8) . ? C14 C15 1.397(7) . ? C15 C16 1.376(6) . ? C16 C17 1.378(6) . ? C16 C19 1.523(5) . ? C17 C18 1.388(6) . ? C19 N20 1.460(5) . ? N20 C21 1.339(5) . ? C21 O21 1.231(4) . ? C21 C22 1.497(5) . ? C22 C23 1.395(5) . ? C22 C27 1.395(5) . ? C23 C24 1.395(5) . ? C24 C25 1.389(5) . ? C24 C28 1.490(5) . ? C25 C26 1.381(5) . ? C26 C27 1.378(5) . ? C28 O28 1.232(4) . ? C28 N29 1.346(4) . ? N29 C30 1.450(4) . ? C30 C31 1.510(5) . ? C31 C32 1.381(5) . ? C31 C36 1.385(5) . ? C32 C33 1.380(5) . ? C33 C34 1.394(5) . ? C34 C35 1.383(5) . ? C35 C36 1.385(5) . ? C37 C66 1.516(6) . ? C37 C60 1.519(6) . ? C37 S38 1.812(4) . ? S38 C39 1.801(4) . ? C39 C40 1.514(5) . ? C40 C41 1.504(5) . ? C41 O41 1.246(4) . ? C41 N42 1.333(4) . ? N42 C43 1.443(5) . ? C43 C44 1.510(6) . ? C44 O44 1.205(4) . ? C44 O45 1.341(4) . ? O45 C46 1.441(4) . ? C46 C47 1.519(5) . ? C47 C54 1.522(5) . ? C47 C48 1.528(5) . ? C48 C53 1.383(5) . ? C48 C49 1.389(5) . ? C49 C50 1.389(5) . ? C50 C51 1.375(5) . ? C51 C52 1.384(5) . ? C52 C53 1.380(5) . ? C54 C55 1.388(5) . ? C54 C59 1.391(6) . ? C55 C56 1.389(6) . ? C56 C57 1.376(6) . ? C57 C58 1.376(6) . ? C58 C59 1.385(6) . ? C60 C65 1.380(6) . ? C60 C61 1.384(6) . ? C61 C62 1.375(6) . ? C62 C63 1.380(6) . ? C63 C64 1.390(6) . ? C64 C65 1.399(6) . ? C66 C67 1.366(8) . ? C66 C71 1.386(9) . ? C67 C68 1.352(11) . ? C68 C69 1.450(19) . ? C69 C70 1.433(16) . ? C70 C71 1.393(8) . ? O1S C1S 1.351(8) . ? 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 N2 C1 C34 110.8(3) . . ? C3 N2 C1 122.5(3) . . ? O3 C3 N2 122.5(4) . . ? O3 C3 C4 119.9(4) . . ? N2 C3 C4 117.6(4) . . ? C9 C4 C5 120.0(4) . . ? C9 C4 C3 116.9(4) . . ? C5 C4 C3 123.1(4) . . ? C4 C5 C6 120.9(4) . . ? C7 C6 C5 117.7(4) . . ? C7 C6 C10 118.3(4) . . ? C5 C6 C10 123.9(4) . . ? C6 C7 C8 121.3(5) . . ? C9 C8 C7 119.6(5) . . ? C8 C9 C4 120.4(5) . . ? O10 C10 N11 121.6(4) . . ? O10 C10 C6 122.2(4) . . ? N11 C10 C6 116.2(4) . . ? C10 N11 C12 120.7(4) . . ? N11 C12 C13 111.0(4) . . ? C14 C13 C18 117.5(5) . . ? C14 C13 C12 121.1(6) . . ? C18 C13 C12 121.4(6) . . ? C13 C14 C15 121.9(5) . . ? C16 C15 C14 120.0(5) . . ? C15 C16 C17 118.3(4) . . ? C15 C16 C19 120.7(4) . . ? C17 C16 C19 121.0(4) . . ? C16 C17 C18 120.6(5) . . ? C13 C18 C17 121.6(5) . . ? N20 C19 C16 113.4(3) . . ? C21 N20 C19 120.9(4) . . ? O21 C21 N20 121.9(4) . . ? O21 C21 C22 120.6(3) . . ? N20 C21 C22 117.4(4) . . ? C23 C22 C27 118.6(3) . . ? C23 C22 C21 116.7(3) . . ? C27 C22 C21 124.7(3) . . ? C24 C23 C22 121.2(3) . . ? C25 C24 C23 118.5(4) . . ? C25 C24 C28 121.2(3) . . ? C23 C24 C28 120.3(3) . . ? C26 C25 C24 120.9(4) . . ? C27 C26 C25 120.1(4) . . ? C26 C27 C22 120.7(4) . . ? O28 C28 N29 123.5(4) . . ? O28 C28 C24 123.4(3) . . ? N29 C28 C24 113.1(3) . . ? C28 N29 C30 125.6(3) . . ? N29 C30 C31 109.9(3) . . ? C32 C31 C36 118.1(4) . . ? C32 C31 C30 119.7(3) . . ? C36 C31 C30 122.1(4) . . ? C31 C32 C33 121.3(3) . . ? C32 C33 C34 120.6(4) . . ? C35 C34 C33 118.1(4) . . ? C35 C34 C1 121.3(3) . . ? C33 C34 C1 120.5(3) . . ? C34 C35 C36 120.9(3) . . ? C31 C36 C35 121.0(4) . . ? C66 C37 C60 114.1(4) . . ? C66 C37 S38 112.6(4) . . ? C60 C37 S38 107.4(3) . . ? C39 S38 C37 101.31(18) . . ? C40 C39 S38 113.4(3) . . ? C41 C40 C39 112.3(3) . . ? O41 C41 N42 120.3(4) . . ? O41 C41 C40 122.9(3) . . ? N42 C41 C40 116.8(3) . . ? C41 N42 C43 119.4(3) . . ? N42 C43 C44 112.2(3) . . ? O44 C44 O45 124.5(4) . . ? O44 C44 C43 125.1(4) . . ? O45 C44 C43 110.3(3) . . ? C44 O45 C46 117.9(3) . . ? O45 C46 C47 107.9(3) . . ? C46 C47 C54 113.2(3) . . ? C46 C47 C48 109.9(3) . . ? C54 C47 C48 113.1(3) . . ? C53 C48 C49 117.8(3) . . ? C53 C48 C47 121.2(3) . . ? C49 C48 C47 120.9(3) . . ? C50 C49 C48 121.3(3) . . ? C51 C50 C49 119.5(4) . . ? C50 C51 C52 120.2(3) . . ? C53 C52 C51 119.7(3) . . ? C48 C53 C52 121.5(3) . . ? C55 C54 C59 118.4(4) . . ? C55 C54 C47 122.8(4) . . ? C59 C54 C47 118.8(3) . . ? C56 C55 C54 120.3(4) . . ? C57 C56 C55 120.9(4) . . ? C58 C57 C56 119.2(4) . . ? C57 C58 C59 120.5(5) . . ? C58 C59 C54 120.8(4) . . ? C65 C60 C61 118.4(4) . . ? C65 C60 C37 122.3(4) . . ? C61 C60 C37 119.3(4) . . ? C62 C61 C60 121.3(4) . . ? C61 C62 C63 120.8(5) . . ? C62 C63 C64 118.7(4) . . ? C63 C64 C65 120.2(4) . . ? C60 C65 C64 120.6(4) . . ? C67 C66 C71 119.3(6) . . ? C67 C66 C37 116.8(7) . . ? C71 C66 C37 123.9(5) . . ? C68 C67 C66 123.6(10) . . ? C67 C68 C69 116.7(12) . . ? C70 C69 C68 121.9(9) . . ? C71 C70 C69 115.3(10) . . ? C66 C71 C70 123.1(8) . . ? 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 C34 C1 N2 C3 -97.3(4) . . . . ? C1 N2 C3 O3 -4.6(6) . . . . ? C1 N2 C3 C4 173.2(3) . . . . ? O3 C3 C4 C9 5.5(7) . . . . ? N2 C3 C4 C9 -172.3(4) . . . . ? O3 C3 C4 C5 -174.5(4) . . . . ? N2 C3 C4 C5 7.6(6) . . . . ? C9 C4 C5 C6 0.1(7) . . . . ? C3 C4 C5 C6 -179.8(4) . . . . ? C4 C5 C6 C7 -1.3(7) . . . . ? C4 C5 C6 C10 176.4(4) . . . . ? C5 C6 C7 C8 1.2(9) . . . . ? C10 C6 C7 C8 -176.7(6) . . . . ? C6 C7 C8 C9 0.2(12) . . . . ? C7 C8 C9 C4 -1.4(12) . . . . ? C5 C4 C9 C8 1.3(9) . . . . ? C3 C4 C9 C8 -178.8(6) . . . . ? C7 C6 C10 O10 -14.9(7) . . . . ? C5 C6 C10 O10 167.4(4) . . . . ? C7 C6 C10 N11 164.7(5) . . . . ? C5 C6 C10 N11 -13.0(7) . . . . ? O10 C10 N11 C12 -0.6(8) . . . . ? C6 C10 N11 C12 179.8(5) . . . . ? C10 N11 C12 C13 154.8(5) . . . . ? N11 C12 C13 C14 99.1(6) . . . . ? N11 C12 C13 C18 -80.7(7) . . . . ? C18 C13 C14 C15 0.9(7) . . . . ? C12 C13 C14 C15 -179.0(4) . . . . ? C13 C14 C15 C16 -0.4(7) . . . . ? C14 C15 C16 C17 0.0(7) . . . . ? C14 C15 C16 C19 -179.9(4) . . . . ? C15 C16 C17 C18 0.0(6) . . . . ? C19 C16 C17 C18 179.9(4) . . . . ? C14 C13 C18 C17 -0.9(7) . . . . ? C12 C13 C18 C17 179.0(4) . . . . ? C16 C17 C18 C13 0.5(7) . . . . ? C15 C16 C19 N20 -141.5(4) . . . . ? C17 C16 C19 N20 38.6(5) . . . . ? C16 C19 N20 C21 77.5(5) . . . . ? C19 N20 C21 O21 0.9(5) . . . . ? C19 N20 C21 C22 -179.1(3) . . . . ? O21 C21 C22 C23 -14.6(5) . . . . ? N20 C21 C22 C23 165.4(3) . . . . ? O21 C21 C22 C27 163.4(4) . . . . ? N20 C21 C22 C27 -16.6(5) . . . . ? C27 C22 C23 C24 1.5(5) . . . . ? C21 C22 C23 C24 179.7(3) . . . . ? C22 C23 C24 C25 -2.6(5) . . . . ? C22 C23 C24 C28 177.2(3) . . . . ? C23 C24 C25 C26 1.6(5) . . . . ? C28 C24 C25 C26 -178.2(3) . . . . ? C24 C25 C26 C27 0.4(6) . . . . ? C25 C26 C27 C22 -1.6(6) . . . . ? C23 C22 C27 C26 0.6(5) . . . . ? C21 C22 C27 C26 -177.3(3) . . . . ? C25 C24 C28 O28 -42.7(5) . . . . ? C23 C24 C28 O28 137.5(4) . . . . ? C25 C24 C28 N29 137.9(4) . . . . ? C23 C24 C28 N29 -41.9(5) . . . . ? O28 C28 N29 C30 -7.3(6) . . . . ? C24 C28 N29 C30 172.1(3) . . . . ? C28 N29 C30 C31 -148.9(3) . . . . ? N29 C30 C31 C32 57.8(5) . . . . ? N29 C30 C31 C36 -118.6(4) . . . . ? C36 C31 C32 C33 0.3(6) . . . . ? C30 C31 C32 C33 -176.2(3) . . . . ? C31 C32 C33 C34 0.0(6) . . . . ? C32 C33 C34 C35 -1.2(5) . . . . ? C32 C33 C34 C1 175.5(3) . . . . ? N2 C1 C34 C35 68.9(4) . . . . ? N2 C1 C34 C33 -107.7(4) . . . . ? C33 C34 C35 C36 2.0(6) . . . . ? C1 C34 C35 C36 -174.7(4) . . . . ? C32 C31 C36 C35 0.5(6) . . . . ? C30 C31 C36 C35 177.0(4) . . . . ? C34 C35 C36 C31 -1.7(6) . . . . ? C66 C37 S38 C39 63.7(3) . . . . ? C60 C37 S38 C39 -169.9(3) . . . . ? C37 S38 C39 C40 72.8(3) . . . . ? S38 C39 C40 C41 177.1(3) . . . . ? C39 C40 C41 O41 22.2(5) . . . . ? C39 C40 C41 N42 -158.2(3) . . . . ? O41 C41 N42 C43 3.0(5) . . . . ? C40 C41 N42 C43 -176.7(3) . . . . ? C41 N42 C43 C44 -61.7(5) . . . . ? N42 C43 C44 O44 -32.8(5) . . . . ? N42 C43 C44 O45 148.8(3) . . . . ? O44 C44 O45 C46 1.3(5) . . . . ? C43 C44 O45 C46 179.7(3) . . . . ? C44 O45 C46 C47 -122.1(3) . . . . ? O45 C46 C47 C54 -162.2(3) . . . . ? O45 C46 C47 C48 70.2(4) . . . . ? C46 C47 C48 C53 78.3(4) . . . . ? C54 C47 C48 C53 -49.3(5) . . . . ? C46 C47 C48 C49 -99.2(4) . . . . ? C54 C47 C48 C49 133.2(4) . . . . ? C53 C48 C49 C50 0.8(6) . . . . ? C47 C48 C49 C50 178.4(4) . . . . ? C48 C49 C50 C51 -0.1(6) . . . . ? C49 C50 C51 C52 -0.7(6) . . . . ? C50 C51 C52 C53 0.8(6) . . . . ? C49 C48 C53 C52 -0.8(6) . . . . ? C47 C48 C53 C52 -178.4(4) . . . . ? C51 C52 C53 C48 0.0(6) . . . . ? C46 C47 C54 C55 -19.0(5) . . . . ? C48 C47 C54 C55 106.9(4) . . . . ? C46 C47 C54 C59 159.9(3) . . . . ? C48 C47 C54 C59 -74.2(4) . . . . ? C59 C54 C55 C56 -1.1(6) . . . . ? C47 C54 C55 C56 177.8(4) . . . . ? C54 C55 C56 C57 0.0(6) . . . . ? C55 C56 C57 C58 1.0(7) . . . . ? C56 C57 C58 C59 -0.9(7) . . . . ? C57 C58 C59 C54 -0.2(6) . . . . ? C55 C54 C59 C58 1.2(6) . . . . ? C47 C54 C59 C58 -177.7(4) . . . . ? C66 C37 C60 C65 18.1(6) . . . . ? S38 C37 C60 C65 -107.5(4) . . . . ? C66 C37 C60 C61 -163.9(4) . . . . ? S38 C37 C60 C61 70.5(4) . . . . ? C65 C60 C61 C62 1.3(6) . . . . ? C37 C60 C61 C62 -176.8(4) . . . . ? C60 C61 C62 C63 -0.6(7) . . . . ? C61 C62 C63 C64 -0.7(7) . . . . ? C62 C63 C64 C65 1.2(6) . . . . ? C61 C60 C65 C64 -0.7(6) . . . . ? C37 C60 C65 C64 177.3(4) . . . . ? C63 C64 C65 C60 -0.6(6) . . . . ? C60 C37 C66 C67 80.0(5) . . . . ? S38 C37 C66 C67 -157.2(4) . . . . ? C60 C37 C66 C71 -97.0(6) . . . . ? S38 C37 C66 C71 25.8(6) . . . . ? C71 C66 C67 C68 -2.8(10) . . . . ? C37 C66 C67 C68 -180.0(7) . . . . ? C66 C67 C68 C69 3.7(15) . . . . ? C67 C68 C69 C70 -3.5(18) . . . . ? C68 C69 C70 C71 2.3(16) . . . . ? C67 C66 C71 C70 1.5(10) . . . . ? C37 C66 C71 C70 178.4(6) . . . . ? C69 C70 C71 C66 -1.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.527 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.058 # Attachment '- sulfonerot8.cif' data_8 _database_code_depnum_ccdc_archive 'CCDC 828038' #TrackingRef '- sulfonerot8.cif' # start Validation Reply Form _vrf_PLAT234_8 ; PROBLEM: Large Hirshfeld Difference C50 -- C51 .. 0.44 Ang. RESPONSE: Correct atom assignment as confirmed by other chemical means. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 N4 O5 S,C32 H31 N O5 S,0.5(C4 H10 O),0.5(C H Cl3)' _chemical_formula_sum 'C66.50 H64.50 Cl1.50 N5 O9.50 S' _chemical_formula_weight 1170.97 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.2159(2) _cell_length_b 19.3091(3) _cell_length_c 20.3924(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.3850(10) _cell_angle_gamma 90.00 _cell_volume 6688.18(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.676363 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27136 _diffrn_reflns_av_R_equivalents 0.1566 _diffrn_reflns_av_sigmaI/netI 0.2049 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 23.27 _reflns_number_total 9530 _reflns_number_gt 3763 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART/SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1817P)^2^+3.5433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9530 _refine_ls_number_parameters 805 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2897 _refine_ls_R_factor_gt 0.1517 _refine_ls_wR_factor_ref 0.4194 _refine_ls_wR_factor_gt 0.3445 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.170 _refine_ls_shift/su_mean 0.019 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 C1 C 0.2694(7) 0.0586(6) 0.4977(6) 0.068(3) Uani 1 1 d . . . H1A H 0.3110 0.0775 0.4761 0.082 Uiso 1 1 calc R . . H1B H 0.2844 0.0120 0.5126 0.082 Uiso 1 1 calc R . . N2 N 0.1979(5) 0.0564(5) 0.4519(5) 0.062(3) Uani 1 1 d D . . H2N H 0.166(5) 0.099(3) 0.444(5) 0.09(4) Uiso 1 1 d D . . C3 C 0.1711(7) 0.0009(6) 0.4151(5) 0.055(3) Uani 1 1 d . . . O3 O 0.2095(5) -0.0515(4) 0.4137(4) 0.075(2) Uani 1 1 d . . . C4 C 0.0921(7) 0.0108(5) 0.3779(5) 0.055(3) Uani 1 1 d . . . C5 C 0.0322(7) 0.0381(5) 0.4097(5) 0.058(3) Uani 1 1 d . . . H5A H 0.0442 0.0497 0.4545 0.069 Uiso 1 1 calc R . . C6 C -0.0446(6) 0.0484(5) 0.3768(5) 0.050(3) Uani 1 1 d . . . C7 C -0.0628(8) 0.0267(6) 0.3093(6) 0.072(4) Uani 1 1 d . . . H7A H -0.1134 0.0335 0.2861 0.086 Uiso 1 1 calc R . . C8 C -0.0070(9) -0.0040(7) 0.2779(6) 0.079(4) Uani 1 1 d . . . H8A H -0.0200 -0.0195 0.2343 0.095 Uiso 1 1 calc R . . C9 C 0.0706(8) -0.0117(6) 0.3128(6) 0.075(4) Uani 1 1 d . . . H9A H 0.1084 -0.0325 0.2915 0.091 Uiso 1 1 calc R . . C10 C -0.1016(7) 0.0802(5) 0.4161(6) 0.054(3) Uani 1 1 d . . . O10 O -0.0852(4) 0.0823(4) 0.4766(4) 0.063(2) Uani 1 1 d . . . N11 N -0.1677(6) 0.1066(5) 0.3818(5) 0.070(3) Uani 1 1 d D . . H11N H -0.183(7) 0.101(7) 0.3335(15) 0.11(5) Uiso 1 1 d D . . C12 C -0.2232(7) 0.1418(6) 0.4171(6) 0.072(4) Uani 1 1 d . . . H12A H -0.2299 0.1146 0.4558 0.086 Uiso 1 1 calc R . . H12B H -0.2739 0.1446 0.3884 0.086 Uiso 1 1 calc R . . C13 C -0.1963(6) 0.2149(6) 0.4395(6) 0.057(3) Uani 1 1 d . . . C14 C -0.1469(7) 0.2518(6) 0.4075(6) 0.067(3) Uani 1 1 d . . . H14A H -0.1270 0.2320 0.3721 0.081 Uiso 1 1 calc R . . C15 C -0.1257(7) 0.3191(6) 0.4273(6) 0.070(3) Uani 1 1 d . . . H15A H -0.0935 0.3444 0.4037 0.084 Uiso 1 1 calc R . . C16 C -0.1520(7) 0.3489(6) 0.4815(6) 0.063(3) Uani 1 1 d . . . C17 C -0.2026(8) 0.3117(7) 0.5144(7) 0.084(4) Uani 1 1 d . . . H17A H -0.2214 0.3312 0.5505 0.101 Uiso 1 1 calc R . . C18 C -0.2254(7) 0.2446(7) 0.4932(7) 0.080(4) Uani 1 1 d . . . H18A H -0.2599 0.2198 0.5149 0.096 Uiso 1 1 calc R . . C19 C -0.1282(7) 0.4222(6) 0.5045(7) 0.078(4) Uani 1 1 d . . . H19A H -0.1161 0.4489 0.4671 0.094 Uiso 1 1 calc R . . H19B H -0.1720 0.4445 0.5206 0.094 Uiso 1 1 calc R . . N20 N -0.0591(5) 0.4222(5) 0.5578(4) 0.056(2) Uani 1 1 d D . . H20N H -0.026(6) 0.384(4) 0.578(5) 0.10(4) Uiso 1 1 d D . . C21 C -0.0272(7) 0.4827(6) 0.5823(6) 0.057(3) Uani 1 1 d . . . O21 O -0.0552(5) 0.5389(4) 0.5592(4) 0.083(3) Uani 1 1 d . . . C22 C 0.0394(6) 0.4804(6) 0.6368(5) 0.057(3) Uani 1 1 d . . . C23 C 0.0904(6) 0.4240(5) 0.6488(5) 0.056(3) Uani 1 1 d . . . H23A H 0.0819 0.3852 0.6215 0.067 Uiso 1 1 calc R . . C24 C 0.1524(6) 0.4247(6) 0.6996(5) 0.056(3) Uani 1 1 d . . . C25 C 0.1659(7) 0.4807(7) 0.7408(6) 0.078(4) Uani 1 1 d . . . H25A H 0.2083 0.4810 0.7755 0.094 Uiso 1 1 calc R . . C26 C 0.1155(9) 0.5373(8) 0.7302(7) 0.096(5) Uani 1 1 d . . . H26A H 0.1228 0.5744 0.7596 0.115 Uiso 1 1 calc R . . C27 C 0.0550(7) 0.5394(6) 0.6768(6) 0.072(4) Uani 1 1 d . . . H27A H 0.0251 0.5794 0.6676 0.087 Uiso 1 1 calc R . . C28 C 0.2056(7) 0.3646(6) 0.7152(5) 0.063(3) Uani 1 1 d . . . O28 O 0.2719(5) 0.3718(4) 0.7474(4) 0.084(3) Uani 1 1 d . . . N29 N 0.1764(5) 0.3014(4) 0.6972(4) 0.064(3) Uani 1 1 d . . . H29N H 0.1249 0.2985 0.6686 0.076 Uiso 1 1 calc R . . C30 C 0.2178(7) 0.2369(7) 0.7181(6) 0.077(4) Uani 1 1 d . . . H30A H 0.1872 0.2113 0.7459 0.092 Uiso 1 1 calc R . . H30B H 0.2680 0.2481 0.7450 0.092 Uiso 1 1 calc R . . C31 C 0.2323(7) 0.1907(6) 0.6610(6) 0.061(3) Uani 1 1 d . . . C32 C 0.1957(9) 0.1273(8) 0.6508(7) 0.092(4) Uani 1 1 d . . . H32A H 0.1616 0.1128 0.6791 0.111 Uiso 1 1 calc R . . C33 C 0.2091(9) 0.0846(6) 0.5989(7) 0.090(4) Uani 1 1 d . . . H33A H 0.1833 0.0422 0.5928 0.107 Uiso 1 1 calc R . . C34 C 0.2589(7) 0.1033(6) 0.5566(6) 0.059(3) Uani 1 1 d . . . C35 C 0.2956(7) 0.1671(7) 0.5679(7) 0.082(4) Uani 1 1 d . . . H35A H 0.3307 0.1809 0.5401 0.099 Uiso 1 1 calc R . . C36 C 0.2826(7) 0.2110(7) 0.6182(7) 0.083(4) Uani 1 1 d . . . H36A H 0.3073 0.2539 0.6234 0.100 Uiso 1 1 calc R . . C37 C 0.1752(6) 0.3432(5) 0.4040(6) 0.059(3) Uani 1 1 d . . . H37A H 0.1397 0.3815 0.4100 0.070 Uiso 1 1 calc R . . S38 S 0.12006(17) 0.26646(15) 0.41502(14) 0.0579(9) Uani 1 1 d . . . O38 O 0.1713(5) 0.2070(4) 0.4192(4) 0.074(2) Uani 1 1 d . . . O39 O 0.0504(4) 0.2665(4) 0.3659(3) 0.075(2) Uani 1 1 d . . . C39 C 0.0903(6) 0.2781(6) 0.4935(5) 0.060(3) Uani 1 1 d . . . H39A H 0.1363 0.2844 0.5274 0.072 Uiso 1 1 calc R . . H39B H 0.0577 0.3191 0.4926 0.072 Uiso 1 1 calc R . . C40 C 0.0444(7) 0.2153(5) 0.5101(5) 0.058(3) Uani 1 1 d . . . H40A H 0.0057 0.2030 0.4719 0.070 Uiso 1 1 calc R . . H40B H 0.0800 0.1765 0.5203 0.070 Uiso 1 1 calc R . . C41 C 0.0032(6) 0.2293(6) 0.5688(5) 0.046(3) Uani 1 1 d . . . O41 O 0.0121(4) 0.2838(4) 0.6004(4) 0.061(2) Uani 1 1 d . . . N42 N -0.0405(5) 0.1770(5) 0.5854(4) 0.055(2) Uani 1 1 d D . . H42N H -0.046(5) 0.135(3) 0.558(4) 0.06(3) Uiso 1 1 d D . . C43 C -0.0843(7) 0.1856(6) 0.6388(5) 0.064(3) Uani 1 1 d . . . H43A H -0.1169 0.1450 0.6414 0.076 Uiso 1 1 calc R . . H43B H -0.1188 0.2253 0.6297 0.076 Uiso 1 1 calc R . . C44 C -0.0313(9) 0.1959(6) 0.7050(7) 0.065(3) Uani 1 1 d . . . O44 O 0.0368(5) 0.1891(5) 0.7176(4) 0.081(3) Uani 1 1 d . . . O45 O -0.0770(5) 0.2170(5) 0.7485(5) 0.094(3) Uani 1 1 d . . . C46 C -0.0378(8) 0.2416(8) 0.8104(7) 0.096(5) Uani 1 1 d . . . H46A H 0.0133 0.2195 0.8211 0.115 Uiso 1 1 calc R . . H46B H -0.0682 0.2299 0.8450 0.115 Uiso 1 1 calc R . . C47 C -0.0275(10) 0.3192(9) 0.8079(7) 0.103(5) Uani 1 1 d . . . H47A H 0.0073 0.3284 0.7753 0.124 Uiso 1 1 calc R . . C48 C 0.0116(9) 0.3529(12) 0.8745(10) 0.118(6) Uani 1 1 d . . . C49 C 0.0303(11) 0.4241(11) 0.8769(11) 0.146(7) Uani 1 1 d . . . H49A H 0.0224 0.4525 0.8395 0.176 Uiso 1 1 calc R . . C50 C 0.0631(13) 0.4496(14) 0.9430(17) 0.208(14) Uani 1 1 d . . . H50A H 0.0710 0.4968 0.9500 0.250 Uiso 1 1 calc R . . C51 C 0.0829(18) 0.404(2) 0.9961(16) 0.216(18) Uani 1 1 d . . . H51A H 0.1123 0.4201 1.0353 0.259 Uiso 1 1 calc R . . C52 C 0.063(2) 0.3414(17) 0.9933(14) 0.199(15) Uani 1 1 d . . . H52A H 0.0711 0.3147 1.0317 0.239 Uiso 1 1 calc R . . C53 C 0.0293(12) 0.3118(13) 0.9342(11) 0.160(8) Uani 1 1 d . . . H53A H 0.0177 0.2647 0.9326 0.192 Uiso 1 1 calc R . . C54 C -0.1083(10) 0.3552(7) 0.7812(8) 0.087(4) Uani 1 1 d . . . C55 C -0.1694(13) 0.3646(8) 0.8198(7) 0.102(5) Uani 1 1 d . . . H55A H -0.1613 0.3521 0.8645 0.122 Uiso 1 1 calc R . . C56 C -0.2400(12) 0.3921(9) 0.7909(15) 0.135(8) Uani 1 1 d . . . H56A H -0.2802 0.3969 0.8160 0.162 Uiso 1 1 calc R . . C57 C -0.2520(16) 0.4121(10) 0.7273(12) 0.148(9) Uani 1 1 d . . . H57A H -0.2999 0.4316 0.7086 0.178 Uiso 1 1 calc R . . C58 C -0.1939(18) 0.4039(9) 0.6899(10) 0.136(8) Uani 1 1 d . . . H58A H -0.2024 0.4176 0.6456 0.163 Uiso 1 1 calc R . . C59 C -0.1223(12) 0.3752(8) 0.7176(9) 0.100(5) Uani 1 1 d . . . H59A H -0.0832 0.3698 0.6915 0.120 Uiso 1 1 calc R . . C60 C 0.2451(7) 0.3525(7) 0.4585(7) 0.067(3) Uani 1 1 d . . . C61 C 0.3131(8) 0.3173(7) 0.4597(7) 0.084(4) Uani 1 1 d . . . H61A H 0.3183 0.2857 0.4263 0.101 Uiso 1 1 calc R . . C62 C 0.3782(8) 0.3293(11) 0.5136(10) 0.117(6) Uani 1 1 d . . . H62A H 0.4262 0.3068 0.5147 0.140 Uiso 1 1 calc R . . C63 C 0.3667(13) 0.3747(10) 0.5628(9) 0.114(7) Uani 1 1 d . . . H63A H 0.4077 0.3816 0.5980 0.136 Uiso 1 1 calc R . . C64 C 0.2993(12) 0.4097(8) 0.5627(9) 0.111(6) Uani 1 1 d . . . H64A H 0.2935 0.4410 0.5963 0.133 Uiso 1 1 calc R . . C65 C 0.2391(8) 0.3971(7) 0.5107(8) 0.087(4) Uani 1 1 d . . . H65A H 0.1915 0.4200 0.5106 0.104 Uiso 1 1 calc R . . C66 C 0.1888(6) 0.3494(6) 0.3338(6) 0.057(3) Uani 1 1 d . . . C67 C 0.2211(7) 0.2972(8) 0.3018(7) 0.084(4) Uani 1 1 d . . . H67A H 0.2343 0.2558 0.3244 0.101 Uiso 1 1 calc R . . C68 C 0.2348(8) 0.3036(10) 0.2374(8) 0.101(5) Uani 1 1 d . . . H68A H 0.2555 0.2664 0.2171 0.121 Uiso 1 1 calc R . . C69 C 0.2188(10) 0.3616(12) 0.2044(8) 0.108(6) Uani 1 1 d . . . H69A H 0.2309 0.3667 0.1618 0.129 Uiso 1 1 calc R . . C70 C 0.1835(10) 0.4155(10) 0.2341(9) 0.115(6) Uani 1 1 d . . . H70A H 0.1699 0.4561 0.2104 0.138 Uiso 1 1 calc R . . C71 C 0.1684(8) 0.4094(7) 0.2987(7) 0.094(4) Uani 1 1 d . . . H71A H 0.1446 0.4455 0.3181 0.113 Uiso 1 1 calc R . . C81 C -0.0739(19) 0.0319(14) 0.8880(13) 0.096(10) Uani 0.50 1 d P . . H81A H -0.1035 0.0285 0.9239 0.144 Uiso 0.50 1 calc PR . . H81B H -0.0690 -0.0131 0.8693 0.144 Uiso 0.50 1 calc PR . . H81C H -0.1006 0.0623 0.8545 0.144 Uiso 0.50 1 calc PR . . C82 C 0.010(3) 0.0613(18) 0.9147(16) 0.117(14) Uani 0.50 1 d P . . H82A H 0.0029 0.1065 0.9339 0.140 Uiso 0.50 1 calc PR . . H82B H 0.0337 0.0315 0.9506 0.140 Uiso 0.50 1 calc PR . . O83 O 0.0531(11) 0.0674(8) 0.8781(7) 0.060(5) Uani 0.50 1 d P . . C84 C 0.1220(15) 0.0943(12) 0.9029(10) 0.061(7) Uani 0.50 1 d P . . H84A H 0.1471 0.0658 0.9395 0.073 Uiso 0.50 1 calc PR . . H84B H 0.1144 0.1402 0.9201 0.073 Uiso 0.50 1 calc PR . . C85 C 0.1687(15) 0.0985(13) 0.8569(12) 0.090(10) Uani 0.50 1 d P . . H85A H 0.2189 0.1169 0.8766 0.135 Uiso 0.50 1 calc PR . . H85B H 0.1451 0.1285 0.8216 0.135 Uiso 0.50 1 calc PR . . H85C H 0.1757 0.0532 0.8393 0.135 Uiso 0.50 1 calc PR . . C90 C 0.5260(13) 0.2603(12) 0.7119(11) 0.069(7) Uiso 0.50 1 d P . . H90A H 0.5642 0.2509 0.7520 0.083 Uiso 0.50 1 calc PR . . Cl1 Cl 0.5718(5) 0.3017(6) 0.6515(6) 0.172(5) Uani 0.50 1 d P . . Cl2 Cl 0.4944(4) 0.1886(5) 0.6759(5) 0.126(3) Uani 0.50 1 d P . . Cl3 Cl 0.4442(6) 0.3064(5) 0.7319(3) 0.126(3) Uani 0.50 1 d P . . 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 C1 0.068(8) 0.051(8) 0.086(9) -0.003(7) 0.015(7) 0.002(6) N2 0.059(6) 0.046(6) 0.073(6) 0.000(5) -0.011(5) 0.013(5) C3 0.066(8) 0.045(8) 0.055(7) -0.005(6) 0.013(6) 0.004(6) O3 0.092(6) 0.047(5) 0.089(6) -0.012(4) 0.025(5) 0.016(5) C4 0.083(9) 0.040(7) 0.044(7) 0.000(5) 0.013(7) 0.023(6) C5 0.088(9) 0.037(7) 0.046(6) -0.007(5) 0.005(7) -0.016(6) C6 0.063(7) 0.034(6) 0.048(7) 0.001(5) -0.010(6) -0.007(5) C7 0.095(10) 0.059(8) 0.051(7) -0.002(7) -0.020(7) -0.018(7) C8 0.097(11) 0.072(10) 0.064(8) -0.019(7) 0.006(9) 0.008(8) C9 0.099(11) 0.063(9) 0.067(9) -0.018(7) 0.024(8) 0.010(7) C10 0.082(9) 0.030(6) 0.049(7) -0.008(6) 0.006(7) -0.002(6) O10 0.065(5) 0.073(6) 0.050(5) -0.005(4) 0.003(4) 0.003(4) N11 0.070(7) 0.055(7) 0.080(8) 0.006(6) -0.002(7) 0.015(5) C12 0.057(8) 0.056(8) 0.096(9) -0.004(7) -0.009(7) -0.013(6) C13 0.048(7) 0.036(7) 0.082(9) -0.004(6) -0.004(6) -0.004(6) C14 0.073(8) 0.045(8) 0.078(8) -0.004(7) -0.003(7) 0.001(6) C15 0.077(9) 0.050(8) 0.086(9) 0.009(7) 0.025(7) 0.009(7) C16 0.055(7) 0.044(7) 0.082(9) -0.002(7) -0.013(7) -0.007(6) C17 0.099(11) 0.061(9) 0.092(10) -0.006(8) 0.015(9) -0.004(8) C18 0.073(9) 0.068(10) 0.100(10) -0.010(8) 0.019(8) -0.014(7) C19 0.063(8) 0.061(9) 0.108(10) -0.011(8) 0.007(8) 0.001(6) N20 0.055(6) 0.043(6) 0.065(6) 0.003(5) 0.000(5) 0.001(5) C21 0.072(8) 0.023(6) 0.081(8) -0.005(6) 0.025(7) 0.008(6) O21 0.101(7) 0.042(5) 0.102(6) -0.006(5) 0.002(5) 0.013(5) C22 0.060(8) 0.051(8) 0.057(7) -0.009(6) 0.002(6) -0.001(6) C23 0.062(8) 0.037(7) 0.068(7) -0.012(6) 0.009(7) -0.009(6) C24 0.060(8) 0.043(7) 0.061(7) -0.012(6) 0.002(6) -0.002(6) C25 0.075(9) 0.065(9) 0.088(9) -0.021(8) -0.007(7) -0.001(7) C26 0.115(12) 0.075(11) 0.092(10) -0.043(9) -0.002(10) -0.009(9) C27 0.089(10) 0.049(8) 0.079(9) -0.007(7) 0.015(8) -0.007(7) C28 0.054(8) 0.069(9) 0.059(7) -0.014(7) -0.012(6) -0.019(7) O28 0.077(6) 0.074(6) 0.090(6) -0.024(5) -0.017(5) -0.005(5) N29 0.070(6) 0.038(6) 0.077(6) -0.007(5) -0.009(5) 0.006(5) C30 0.088(9) 0.072(9) 0.064(8) -0.008(7) -0.005(7) 0.013(7) C31 0.067(8) 0.032(7) 0.079(8) 0.000(6) -0.003(7) -0.003(6) C32 0.114(12) 0.080(11) 0.087(10) 0.008(9) 0.029(9) -0.006(9) C33 0.136(13) 0.043(8) 0.100(10) -0.025(8) 0.051(10) -0.026(8) C34 0.060(8) 0.051(8) 0.064(8) -0.003(7) 0.005(6) 0.014(6) C35 0.086(10) 0.076(10) 0.089(10) -0.028(8) 0.024(8) -0.031(8) C36 0.081(9) 0.061(9) 0.111(11) -0.019(8) 0.026(9) -0.034(7) C37 0.053(7) 0.035(6) 0.090(9) 0.000(6) 0.014(7) 0.014(5) S38 0.0578(18) 0.0475(18) 0.067(2) 0.0054(16) 0.0072(16) -0.0027(15) O38 0.085(6) 0.038(5) 0.103(6) 0.005(4) 0.031(5) 0.015(4) O39 0.066(5) 0.090(6) 0.063(5) 0.001(5) -0.003(4) -0.012(4) C39 0.061(7) 0.062(8) 0.057(7) 0.001(6) 0.010(6) -0.002(6) C40 0.096(9) 0.027(6) 0.048(7) 0.001(5) 0.000(6) -0.005(6) C41 0.061(7) 0.034(7) 0.042(6) 0.006(6) 0.005(5) 0.009(6) O41 0.073(5) 0.035(5) 0.076(5) -0.003(4) 0.011(4) -0.004(4) N42 0.067(6) 0.036(6) 0.064(6) -0.004(5) 0.016(5) -0.009(5) C43 0.069(8) 0.060(8) 0.065(8) 0.010(6) 0.022(7) -0.004(6) C44 0.074(9) 0.055(8) 0.076(9) 0.004(7) 0.036(9) 0.007(7) O44 0.060(6) 0.106(7) 0.080(6) 0.000(5) 0.018(5) 0.023(5) O45 0.092(7) 0.111(8) 0.081(6) -0.037(6) 0.021(6) -0.008(5) C46 0.088(10) 0.119(14) 0.082(10) -0.025(10) 0.019(8) -0.005(9) C47 0.132(14) 0.108(13) 0.076(10) -0.016(10) 0.037(10) -0.072(12) C48 0.085(11) 0.16(2) 0.115(15) -0.003(14) 0.031(11) -0.010(12) C49 0.145(17) 0.102(16) 0.19(2) -0.005(15) 0.032(15) -0.044(13) C50 0.124(17) 0.17(2) 0.31(3) -0.18(3) -0.02(2) -0.049(17) C51 0.14(2) 0.36(6) 0.14(2) -0.01(3) -0.019(18) 0.04(3) C52 0.28(3) 0.21(3) 0.110(18) -0.05(2) 0.018(19) -0.08(3) C53 0.167(19) 0.20(2) 0.111(15) -0.032(17) 0.009(14) -0.065(16) C54 0.120(14) 0.071(10) 0.067(10) -0.007(8) 0.006(10) -0.024(9) C55 0.169(17) 0.079(11) 0.069(10) -0.013(8) 0.054(12) -0.049(11) C56 0.096(14) 0.084(14) 0.22(3) -0.035(15) 0.017(16) 0.000(11) C57 0.25(3) 0.081(14) 0.105(16) -0.010(13) -0.006(18) 0.048(15) C58 0.27(3) 0.051(11) 0.086(14) -0.010(10) 0.037(18) 0.002(14) C59 0.156(17) 0.068(11) 0.081(13) -0.006(9) 0.036(11) -0.019(11) C60 0.055(8) 0.061(9) 0.084(9) 0.012(8) 0.006(7) -0.004(7) C61 0.075(10) 0.069(9) 0.105(11) 0.014(8) 0.006(9) -0.004(8) C62 0.052(9) 0.156(18) 0.133(15) 0.068(14) -0.015(10) -0.018(10) C63 0.16(2) 0.092(14) 0.082(12) -0.001(11) -0.009(12) -0.049(13) C64 0.129(15) 0.056(10) 0.138(15) -0.003(10) -0.008(13) -0.016(10) C65 0.068(9) 0.067(10) 0.116(12) 0.007(9) -0.014(9) -0.024(7) C66 0.052(7) 0.049(8) 0.069(8) 0.030(7) 0.011(6) 0.009(6) C67 0.080(9) 0.090(11) 0.087(10) 0.031(9) 0.025(8) 0.020(8) C68 0.098(12) 0.117(15) 0.094(12) 0.038(11) 0.034(9) 0.003(10) C69 0.099(13) 0.140(17) 0.091(12) -0.012(13) 0.037(10) -0.052(12) C70 0.145(15) 0.106(15) 0.091(12) 0.065(11) 0.016(11) -0.037(12) C71 0.113(12) 0.072(10) 0.099(11) 0.016(9) 0.026(9) -0.010(8) C81 0.15(3) 0.08(2) 0.072(18) -0.003(16) 0.09(2) 0.04(2) C82 0.18(4) 0.09(2) 0.07(2) -0.03(2) -0.02(2) 0.06(3) O83 0.090(13) 0.060(11) 0.028(9) -0.012(8) 0.004(9) 0.002(9) C84 0.086(18) 0.054(15) 0.031(13) -0.001(12) -0.023(13) -0.021(14) C85 0.11(2) 0.071(18) 0.070(17) 0.061(15) -0.055(17) -0.051(16) Cl1 0.086(6) 0.175(10) 0.236(12) 0.105(9) -0.029(7) -0.002(6) Cl2 0.072(5) 0.130(8) 0.170(8) -0.040(6) 0.003(5) 0.004(5) Cl3 0.187(9) 0.129(7) 0.054(4) -0.011(4) -0.004(5) 0.071(6) _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 C1 N2 1.419(13) . ? C1 C34 1.515(15) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N2 C3 1.346(13) . ? N2 H2N 0.98(2) . ? C3 O3 1.212(12) . ? C3 C4 1.457(15) . ? C4 C9 1.389(14) . ? C4 C5 1.407(14) . ? C5 C6 1.395(14) . ? C5 H5A 0.9300 . ? C6 C7 1.423(14) . ? C6 C10 1.497(15) . ? C7 C8 1.374(16) . ? C7 H7A 0.9300 . ? C8 C9 1.417(16) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 O10 1.221(11) . ? C10 N11 1.336(14) . ? N11 C12 1.454(14) . ? N11 H11N 0.98(2) . ? C12 C13 1.532(15) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.357(15) . ? C13 C18 1.398(15) . ? C14 C15 1.390(15) . ? C14 H14A 0.9300 . ? C15 C16 1.387(15) . ? C15 H15A 0.9300 . ? C16 C17 1.385(16) . ? C16 C19 1.526(15) . ? C17 C18 1.401(17) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 N20 1.474(13) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? N20 C21 1.352(13) . ? N20 H20N 0.99(2) . ? C21 O21 1.248(12) . ? C21 C22 1.461(15) . ? C22 C23 1.395(14) . ? C22 C27 1.403(15) . ? C23 C24 1.361(14) . ? C23 H23A 0.9300 . ? C24 C25 1.366(15) . ? C24 C28 1.480(15) . ? C25 C26 1.390(17) . ? C25 H25A 0.9300 . ? C26 C27 1.378(16) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C28 O28 1.229(11) . ? C28 N29 1.348(13) . ? N29 C30 1.463(13) . ? N29 H29N 0.9800 . ? C30 C31 1.521(15) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C36 1.382(15) . ? C31 C32 1.378(16) . ? C32 C33 1.391(16) . ? C32 H32A 0.9300 . ? C33 C34 1.358(15) . ? C33 H33A 0.9300 . ? C34 C35 1.387(16) . ? C35 C36 1.378(16) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? C37 C66 1.493(15) . ? C37 C60 1.510(15) . ? C37 S38 1.793(11) . ? C37 H37A 0.9800 . ? S38 O39 1.432(7) . ? S38 O38 1.441(7) . ? S38 C39 1.773(10) . ? C39 C40 1.515(14) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.511(14) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 O41 1.230(11) . ? C41 N42 1.335(13) . ? N42 C43 1.432(13) . ? N42 H42N 0.97(2) . ? C43 C44 1.514(16) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 O44 1.165(13) . ? C44 O45 1.341(13) . ? O45 C46 1.412(14) . ? C46 C47 1.511(19) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.56(2) . ? C47 C54 1.57(2) . ? C47 H47A 0.9800 . ? C48 C49 1.41(2) . ? C48 C53 1.44(2) . ? C49 C50 1.46(3) . ? C49 H49A 0.9300 . ? C50 C51 1.40(4) . ? C50 H50A 0.9300 . ? C51 C52 1.25(4) . ? C51 H51A 0.9300 . ? C52 C53 1.37(3) . ? C52 H52A 0.9300 . ? C53 H53A 0.9300 . ? C54 C59 1.337(19) . ? C54 C55 1.424(19) . ? C55 C56 1.37(2) . ? C55 H55A 0.9300 . ? C56 C57 1.34(2) . ? C56 H56A 0.9300 . ? C57 C58 1.36(3) . ? C57 H57A 0.9300 . ? C58 C59 1.39(2) . ? C58 H58A 0.9300 . ? C59 H59A 0.9300 . ? C60 C61 1.350(16) . ? C60 C65 1.387(17) . ? C61 C62 1.455(19) . ? C61 H61A 0.9300 . ? C62 C63 1.37(2) . ? C62 H62A 0.9300 . ? C63 C64 1.34(2) . ? C63 H63A 0.9300 . ? C64 C65 1.379(19) . ? C64 H64A 0.9300 . ? C65 H65A 0.9300 . ? C66 C67 1.368(16) . ? C66 C71 1.376(16) . ? C67 C68 1.377(18) . ? C67 H67A 0.9300 . ? C68 C69 1.31(2) . ? C68 H68A 0.9300 . ? C69 C70 1.39(2) . ? C69 H69A 0.9300 . ? C70 C71 1.39(2) . ? C70 H70A 0.9300 . ? C71 H71A 0.9300 . ? C81 C82 1.56(4) . ? C81 H81A 0.9600 . ? C81 H81B 0.9600 . ? C81 H81C 0.9600 . ? C82 O83 1.15(4) . ? C82 H82A 0.9700 . ? C82 H82B 0.9700 . ? O83 C84 1.32(2) . ? C84 C85 1.33(3) . ? C84 H84A 0.9700 . ? C84 H84B 0.9700 . ? C85 H85A 0.9600 . ? C85 H85B 0.9600 . ? C85 H85C 0.9600 . ? C90 Cl2 1.62(2) . ? C90 Cl1 1.76(2) . ? C90 Cl3 1.77(2) . ? C90 H90A 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 N2 C1 C34 109.6(9) . . ? N2 C1 H1A 109.8 . . ? C34 C1 H1A 109.7 . . ? N2 C1 H1B 109.8 . . ? C34 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C3 N2 C1 124.9(10) . . ? C3 N2 H2N 116(7) . . ? C1 N2 H2N 119(7) . . ? O3 C3 N2 122.6(11) . . ? O3 C3 C4 124.4(11) . . ? N2 C3 C4 113.0(10) . . ? C9 C4 C5 117.2(11) . . ? C9 C4 C3 122.4(11) . . ? C5 C4 C3 120.1(10) . . ? C6 C5 C4 122.6(10) . . ? C6 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? C5 C6 C7 117.8(11) . . ? C5 C6 C10 116.9(9) . . ? C7 C6 C10 125.2(11) . . ? C8 C7 C6 121.1(12) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.5 . . ? C7 C8 C9 119.0(11) . . ? C7 C8 H8A 120.5 . . ? C9 C8 H8A 120.5 . . ? C4 C9 C8 122.0(11) . . ? C4 C9 H9A 119.0 . . ? C8 C9 H9A 119.0 . . ? O10 C10 N11 123.6(11) . . ? O10 C10 C6 119.4(11) . . ? N11 C10 C6 117.0(10) . . ? C10 N11 C12 119.4(10) . . ? C10 N11 H11N 124(8) . . ? C12 N11 H11N 117(8) . . ? N11 C12 C13 112.8(10) . . ? N11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C18 119.6(11) . . ? C14 C13 C12 121.5(12) . . ? C18 C13 C12 118.9(11) . . ? C13 C14 C15 120.4(12) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C16 C15 C14 121.0(12) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C17 C16 C15 118.9(11) . . ? C17 C16 C19 119.4(12) . . ? C15 C16 C19 121.7(12) . . ? C16 C17 C18 119.8(13) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C13 C18 C17 120.2(12) . . ? C13 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? N20 C19 C16 111.7(9) . . ? N20 C19 H19A 109.3 . . ? C16 C19 H19A 109.3 . . ? N20 C19 H19B 109.3 . . ? C16 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C21 N20 C19 120.1(9) . . ? C21 N20 H20N 109(7) . . ? C19 N20 H20N 131(7) . . ? O21 C21 N20 120.3(11) . . ? O21 C21 C22 121.4(10) . . ? N20 C21 C22 118.4(10) . . ? C23 C22 C27 118.4(10) . . ? C23 C22 C21 123.4(10) . . ? C27 C22 C21 118.1(11) . . ? C24 C23 C22 121.3(10) . . ? C24 C23 H23A 119.3 . . ? C22 C23 H23A 119.4 . . ? C23 C24 C25 120.6(11) . . ? C23 C24 C28 122.5(10) . . ? C25 C24 C28 116.8(10) . . ? C24 C25 C26 119.2(12) . . ? C24 C25 H25A 120.4 . . ? C26 C25 H25A 120.4 . . ? C27 C26 C25 121.2(12) . . ? C27 C26 H26A 119.4 . . ? C25 C26 H26A 119.4 . . ? C26 C27 C22 119.0(12) . . ? C26 C27 H27A 120.5 . . ? C22 C27 H27A 120.5 . . ? O28 C28 N29 121.3(11) . . ? O28 C28 C24 121.0(11) . . ? N29 C28 C24 117.5(10) . . ? C28 N29 C30 123.4(10) . . ? C28 N29 H29N 118.3 . . ? C30 N29 H29N 118.3 . . ? N29 C30 C31 114.1(9) . . ? N29 C30 H30A 108.7 . . ? C31 C30 H30A 108.7 . . ? N29 C30 H30B 108.7 . . ? C31 C30 H30B 108.7 . . ? H30A C30 H30B 107.6 . . ? C36 C31 C32 118.4(12) . . ? C36 C31 C30 121.0(11) . . ? C32 C31 C30 120.6(12) . . ? C31 C32 C33 120.8(13) . . ? C31 C32 H32A 119.6 . . ? C33 C32 H32A 119.6 . . ? C34 C33 C32 121.8(12) . . ? C34 C33 H33A 119.1 . . ? C32 C33 H33A 119.1 . . ? C33 C34 C35 116.7(11) . . ? C33 C34 C1 121.4(11) . . ? C35 C34 C1 121.8(12) . . ? C36 C35 C34 122.9(12) . . ? C36 C35 H35A 118.5 . . ? C34 C35 H35A 118.5 . . ? C35 C36 C31 119.4(12) . . ? C35 C36 H36A 120.3 . . ? C31 C36 H36A 120.3 . . ? C66 C37 C60 117.7(9) . . ? C66 C37 S38 110.9(8) . . ? C60 C37 S38 112.4(8) . . ? C66 C37 H37A 104.9 . . ? C60 C37 H37A 104.9 . . ? S38 C37 H37A 104.9 . . ? O39 S38 O38 118.5(5) . . ? O39 S38 C39 107.4(5) . . ? O38 S38 C39 108.2(5) . . ? O39 S38 C37 108.2(5) . . ? O38 S38 C37 109.5(5) . . ? C39 S38 C37 104.2(5) . . ? C40 C39 S38 109.8(8) . . ? C40 C39 H39A 109.7 . . ? S38 C39 H39A 109.7 . . ? C40 C39 H39B 109.7 . . ? S38 C39 H39B 109.7 . . ? H39A C39 H39B 108.2 . . ? C41 C40 C39 111.3(9) . . ? C41 C40 H40A 109.4 . . ? C39 C40 H40A 109.4 . . ? C41 C40 H40B 109.4 . . ? C39 C40 H40B 109.4 . . ? H40A C40 H40B 108.0 . . ? O41 C41 N42 122.7(10) . . ? O41 C41 C40 122.2(10) . . ? N42 C41 C40 115.0(9) . . ? C41 N42 C43 119.6(9) . . ? C41 N42 H42N 119(6) . . ? C43 N42 H42N 121(6) . . ? N42 C43 C44 112.2(9) . . ? N42 C43 H43A 109.2 . . ? C44 C43 H43A 109.2 . . ? N42 C43 H43B 109.2 . . ? C44 C43 H43B 109.2 . . ? H43A C43 H43B 107.9 . . ? O44 C44 O45 124.5(13) . . ? O44 C44 C43 128.3(12) . . ? O45 C44 C43 107.3(11) . . ? C44 O45 C46 116.6(11) . . ? O45 C46 C47 110.2(12) . . ? O45 C46 H46A 109.6 . . ? C47 C46 H46A 109.6 . . ? O45 C46 H46B 109.6 . . ? C47 C46 H46B 109.6 . . ? H46A C46 H46B 108.1 . . ? C46 C47 C48 114.9(15) . . ? C46 C47 C54 110.3(12) . . ? C48 C47 C54 110.5(14) . . ? C46 C47 H47A 106.9 . . ? C48 C47 H47A 106.9 . . ? C54 C47 H47A 106.9 . . ? C49 C48 C53 119.5(19) . . ? C49 C48 C47 120.0(19) . . ? C53 C48 C47 120.6(19) . . ? C48 C49 C50 114(2) . . ? C48 C49 H49A 122.8 . . ? C50 C49 H49A 123.0 . . ? C51 C50 C49 121(3) . . ? C51 C50 H50A 119.9 . . ? C49 C50 H50A 119.4 . . ? C52 C51 C50 123(4) . . ? C52 C51 H51A 118.6 . . ? C50 C51 H51A 118.4 . . ? C51 C52 C53 121(4) . . ? C51 C52 H52A 119.5 . . ? C53 C52 H52A 119.5 . . ? C52 C53 C48 121(2) . . ? C52 C53 H53A 119.5 . . ? C48 C53 H53A 119.7 . . ? C59 C54 C55 117.9(16) . . ? C59 C54 C47 118.2(17) . . ? C55 C54 C47 123.8(15) . . ? C56 C55 C54 119.7(16) . . ? C56 C55 H55A 120.3 . . ? C54 C55 H55A 120.0 . . ? C57 C56 C55 121(2) . . ? C57 C56 H56A 119.5 . . ? C55 C56 H56A 119.4 . . ? C56 C57 C58 120(2) . . ? C56 C57 H57A 120.0 . . ? C58 C57 H57A 120.1 . . ? C57 C58 C59 120(2) . . ? C57 C58 H58A 119.8 . . ? C59 C58 H58A 119.9 . . ? C54 C59 C58 121.2(18) . . ? C54 C59 H59A 119.4 . . ? C58 C59 H59A 119.4 . . ? C61 C60 C65 118.2(13) . . ? C61 C60 C37 122.6(13) . . ? C65 C60 C37 119.2(11) . . ? C60 C61 C62 119.5(15) . . ? C60 C61 H61A 120.2 . . ? C62 C61 H61A 120.2 . . ? C63 C62 C61 118.0(16) . . ? C63 C62 H62A 121.0 . . ? C61 C62 H62A 121.0 . . ? C64 C63 C62 123.3(18) . . ? C64 C63 H63A 118.4 . . ? C62 C63 H63A 118.4 . . ? C63 C64 C65 117.0(18) . . ? C63 C64 H64A 121.5 . . ? C65 C64 H64A 121.5 . . ? C64 C65 C60 124.0(15) . . ? C64 C65 H65A 118.0 . . ? C60 C65 H65A 118.0 . . ? C67 C66 C71 117.5(12) . . ? C67 C66 C37 122.5(10) . . ? C71 C66 C37 120.0(12) . . ? C66 C67 C68 122.2(13) . . ? C66 C67 H67A 118.9 . . ? C68 C67 H67A 118.9 . . ? C69 C68 C67 120.9(17) . . ? C69 C68 H68A 119.5 . . ? C67 C68 H68A 119.6 . . ? C68 C69 C70 118.9(16) . . ? C68 C69 H69A 120.6 . . ? C70 C69 H69A 120.5 . . ? C71 C70 C69 120.8(15) . . ? C71 C70 H70A 119.6 . . ? C69 C70 H70A 119.6 . . ? C66 C71 C70 119.6(15) . . ? C66 C71 H71A 120.2 . . ? C70 C71 H71A 120.2 . . ? C82 C81 H81A 109.4 . . ? C82 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? C82 C81 H81C 109.6 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? O83 C82 C81 118(3) . . ? O83 C82 H82A 107.7 . . ? C81 C82 H82A 107.7 . . ? O83 C82 H82B 107.8 . . ? C81 C82 H82B 107.8 . . ? H82A C82 H82B 107.1 . . ? C82 O83 C84 116(2) . . ? O83 C84 C85 111.2(19) . . ? O83 C84 H84A 109.4 . . ? C85 C84 H84A 109.4 . . ? O83 C84 H84B 109.4 . . ? C85 C84 H84B 109.4 . . ? H84A C84 H84B 108.0 . . ? C84 C85 H85A 109.5 . . ? C84 C85 H85B 109.4 . . ? H85A C85 H85B 109.5 . . ? C84 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? Cl2 C90 Cl1 103.2(13) . . ? Cl2 C90 Cl3 108.3(13) . . ? Cl1 C90 Cl3 113.4(14) . . ? Cl2 C90 H90A 110.6 . . ? Cl1 C90 H90A 110.6 . . ? Cl3 C90 H90A 110.6 . . ? 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 C34 C1 N2 C3 -144.6(11) . . . . ? C1 N2 C3 O3 -6.4(18) . . . . ? C1 N2 C3 C4 173.6(10) . . . . ? O3 C3 C4 C9 -41.0(17) . . . . ? N2 C3 C4 C9 139.0(11) . . . . ? O3 C3 C4 C5 132.7(12) . . . . ? N2 C3 C4 C5 -47.3(14) . . . . ? C9 C4 C5 C6 -5.6(15) . . . . ? C3 C4 C5 C6 -179.7(10) . . . . ? C4 C5 C6 C7 3.4(15) . . . . ? C4 C5 C6 C10 -177.7(9) . . . . ? C5 C6 C7 C8 0.7(16) . . . . ? C10 C6 C7 C8 -178.0(11) . . . . ? C6 C7 C8 C9 -2.4(18) . . . . ? C5 C4 C9 C8 3.8(17) . . . . ? C3 C4 C9 C8 177.7(11) . . . . ? C7 C8 C9 C4 0.0(19) . . . . ? C5 C6 C10 O10 -15.4(14) . . . . ? C7 C6 C10 O10 163.4(10) . . . . ? C5 C6 C10 N11 163.1(9) . . . . ? C7 C6 C10 N11 -18.2(15) . . . . ? O10 C10 N11 C12 1.8(16) . . . . ? C6 C10 N11 C12 -176.5(9) . . . . ? C10 N11 C12 C13 76.7(13) . . . . ? N11 C12 C13 C14 25.4(15) . . . . ? N11 C12 C13 C18 -156.3(10) . . . . ? C18 C13 C14 C15 -0.7(16) . . . . ? C12 C13 C14 C15 177.6(10) . . . . ? C13 C14 C15 C16 2.5(17) . . . . ? C14 C15 C16 C17 -2.6(17) . . . . ? C14 C15 C16 C19 179.0(10) . . . . ? C15 C16 C17 C18 0.9(18) . . . . ? C19 C16 C17 C18 179.4(11) . . . . ? C14 C13 C18 C17 -1.0(17) . . . . ? C12 C13 C18 C17 -179.3(11) . . . . ? C16 C17 C18 C13 0.9(19) . . . . ? C17 C16 C19 N20 86.9(13) . . . . ? C15 C16 C19 N20 -94.7(13) . . . . ? C16 C19 N20 C21 176.8(10) . . . . ? C19 N20 C21 O21 -1.2(16) . . . . ? C19 N20 C21 C22 177.8(9) . . . . ? O21 C21 C22 C23 -156.0(11) . . . . ? N20 C21 C22 C23 25.0(16) . . . . ? O21 C21 C22 C27 20.6(16) . . . . ? N20 C21 C22 C27 -158.4(10) . . . . ? C27 C22 C23 C24 2.4(16) . . . . ? C21 C22 C23 C24 179.0(10) . . . . ? C22 C23 C24 C25 0.6(17) . . . . ? C22 C23 C24 C28 177.5(10) . . . . ? C23 C24 C25 C26 -0.1(19) . . . . ? C28 C24 C25 C26 -177.1(12) . . . . ? C24 C25 C26 C27 -4(2) . . . . ? C25 C26 C27 C22 7(2) . . . . ? C23 C22 C27 C26 -5.9(17) . . . . ? C21 C22 C27 C26 177.3(11) . . . . ? C23 C24 C28 O28 159.3(11) . . . . ? C25 C24 C28 O28 -23.7(17) . . . . ? C23 C24 C28 N29 -25.6(16) . . . . ? C25 C24 C28 N29 151.3(11) . . . . ? O28 C28 N29 C30 4.6(18) . . . . ? C24 C28 N29 C30 -170.4(10) . . . . ? C28 N29 C30 C31 -122.9(12) . . . . ? N29 C30 C31 C36 66.5(15) . . . . ? N29 C30 C31 C32 -113.7(13) . . . . ? C36 C31 C32 C33 0.1(19) . . . . ? C30 C31 C32 C33 -179.7(11) . . . . ? C31 C32 C33 C34 1(2) . . . . ? C32 C33 C34 C35 -0.1(19) . . . . ? C32 C33 C34 C1 -176.2(12) . . . . ? N2 C1 C34 C33 65.4(14) . . . . ? N2 C1 C34 C35 -110.6(12) . . . . ? C33 C34 C35 C36 -1.0(19) . . . . ? C1 C34 C35 C36 175.1(12) . . . . ? C34 C35 C36 C31 2(2) . . . . ? C32 C31 C36 C35 -1.2(19) . . . . ? C30 C31 C36 C35 178.6(11) . . . . ? C66 C37 S38 O39 -52.8(8) . . . . ? C60 C37 S38 O39 173.2(8) . . . . ? C66 C37 S38 O38 77.6(8) . . . . ? C60 C37 S38 O38 -56.4(10) . . . . ? C66 C37 S38 C39 -166.9(7) . . . . ? C60 C37 S38 C39 59.1(9) . . . . ? O39 S38 C39 C40 66.9(9) . . . . ? O38 S38 C39 C40 -62.0(9) . . . . ? C37 S38 C39 C40 -178.5(8) . . . . ? S38 C39 C40 C41 -167.7(7) . . . . ? C39 C40 C41 O41 -4.7(14) . . . . ? C39 C40 C41 N42 178.2(9) . . . . ? O41 C41 N42 C43 5.1(15) . . . . ? C40 C41 N42 C43 -177.8(9) . . . . ? C41 N42 C43 C44 -64.8(13) . . . . ? N42 C43 C44 O44 -10.3(18) . . . . ? N42 C43 C44 O45 167.9(9) . . . . ? O44 C44 O45 C46 9.4(18) . . . . ? C43 C44 O45 C46 -169.0(11) . . . . ? C44 O45 C46 C47 92.7(14) . . . . ? O45 C46 C47 C48 177.3(12) . . . . ? O45 C46 C47 C54 51.5(15) . . . . ? C46 C47 C48 C49 174.7(15) . . . . ? C54 C47 C48 C49 -59.6(19) . . . . ? C46 C47 C48 C53 -5(2) . . . . ? C54 C47 C48 C53 120.5(18) . . . . ? C53 C48 C49 C50 -3(3) . . . . ? C47 C48 C49 C50 177.1(16) . . . . ? C48 C49 C50 C51 8(4) . . . . ? C49 C50 C51 C52 -12(6) . . . . ? C50 C51 C52 C53 9(6) . . . . ? C51 C52 C53 C48 -4(5) . . . . ? C49 C48 C53 C52 1(3) . . . . ? C47 C48 C53 C52 -179(2) . . . . ? C46 C47 C54 C59 -100.6(15) . . . . ? C48 C47 C54 C59 131.2(14) . . . . ? C46 C47 C54 C55 76.1(16) . . . . ? C48 C47 C54 C55 -52.1(18) . . . . ? C59 C54 C55 C56 1(2) . . . . ? C47 C54 C55 C56 -175.4(14) . . . . ? C54 C55 C56 C57 -2(2) . . . . ? C55 C56 C57 C58 1(3) . . . . ? C56 C57 C58 C59 0(3) . . . . ? C55 C54 C59 C58 0(2) . . . . ? C47 C54 C59 C58 176.6(14) . . . . ? C57 C58 C59 C54 0(3) . . . . ? C66 C37 C60 C61 -51.6(15) . . . . ? S38 C37 C60 C61 79.0(13) . . . . ? C66 C37 C60 C65 130.5(12) . . . . ? S38 C37 C60 C65 -98.8(11) . . . . ? C65 C60 C61 C62 -2.4(18) . . . . ? C37 C60 C61 C62 179.7(11) . . . . ? C60 C61 C62 C63 2(2) . . . . ? C61 C62 C63 C64 -2(3) . . . . ? C62 C63 C64 C65 1(3) . . . . ? C63 C64 C65 C60 -2(2) . . . . ? C61 C60 C65 C64 2(2) . . . . ? C37 C60 C65 C64 -179.7(12) . . . . ? C60 C37 C66 C67 78.6(14) . . . . ? S38 C37 C66 C67 -52.7(13) . . . . ? C60 C37 C66 C71 -101.8(13) . . . . ? S38 C37 C66 C71 126.9(10) . . . . ? C71 C66 C67 C68 1.4(19) . . . . ? C37 C66 C67 C68 -179.0(12) . . . . ? C66 C67 C68 C69 2(2) . . . . ? C67 C68 C69 C70 -4(2) . . . . ? C68 C69 C70 C71 3(2) . . . . ? C67 C66 C71 C70 -2.3(19) . . . . ? C37 C66 C71 C70 178.1(12) . . . . ? C69 C70 C71 C66 0(2) . . . . ? C81 C82 O83 C84 178(2) . . . . ? C82 O83 C84 C85 179(3) . . . . ? 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 N2 H2N O38 0.98(2) 2.16(7) 3.002(12) 143(9) . N11 H11N O28 0.98(2) 1.87(6) 2.799(13) 156(11) 4_565 N20 H20N O41 0.99(2) 2.07(5) 3.009(11) 160(10) . N29 H29N O41 0.98 2.22 3.193(12) 175.1 . N42 H42N O10 0.97(2) 1.98(5) 2.881(11) 153(8) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.150 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.103 data_enbac3 _database_code_depnum_ccdc_archive 'CCDC 829630' #TrackingRef 'Souza_1308057332.sulfoxide.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 18.83840(10) _cell_length_b 17.3439(2) _cell_length_c 19.0355(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.4120(10) _cell_angle_gamma 90.00 _cell_volume 6219.33 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1 C 0.4501(5) 0.0859(6) 0.0827(6) H1A H 0.4516(5) 0.1067(6) 0.0354(6) H1B H 0.4983(5) 0.0861(6) 0.1012(6) N2 N 0.4258(4) 0.0074(4) 0.0790(4) H2N H 0.3803(22) -0.0194(43) 0.0848(44) C3 C 0.4650(5) -0.0541(6) 0.0954(5) O3 O 0.5270(4) -0.0438(4) 0.1158(5) C4 C 0.4352(4) -0.1313(5) 0.0902(4) C5 C 0.3648(4) -0.1456(5) 0.0772(4) H5A H 0.3342(4) -0.1043(5) 0.0695(4) C6 C 0.3383(5) -0.2197(5) 0.0752(4) C7 C 0.3839(5) -0.2812(5) 0.0874(5) H7A H 0.3673(5) -0.3317(5) 0.0875(5) C8 C 0.4558(5) -0.2647(7) 0.0997(5) H8A H 0.4877(5) -0.3050(7) 0.1071(5) C9 C 0.4794(5) -0.1917(6) 0.1008(5) H9A H 0.5273(5) -0.1823(6) 0.1091(5) C10 C 0.2607(5) -0.2387(6) 0.0627(5) O10 O 0.2353(3) -0.2967(4) 0.0844(4) N11 N 0.2228(4) -0.1841(4) 0.0289(4) H11N H 0.2466(30) -0.1405(24) 0.0064(30) C12 C 0.1467(5) -0.1927(6) 0.0135(5) H12A H 0.1343(5) -0.2469(6) 0.0150(5) H12B H 0.1371(5) -0.1741(6) -0.0337(5) C13 C 0.1013(4) -0.1494(5) 0.0642(5) C14 C 0.0733(4) -0.0791(6) 0.0455(5) H14A H 0.0804(4) -0.0600(6) 0.0004(5) C15 C 0.0347(5) -0.0366(5) 0.0928(5) H15A H 0.0158(5) 0.0106(5) 0.0790(5) C16 C 0.0235(4) -0.0624(5) 0.1598(5) C17 C 0.0495(5) -0.1333(6) 0.1774(5) H17A H 0.0410(5) -0.1531(6) 0.2219(5) C18 C 0.0880(5) -0.1760(6) 0.1302(6) H18A H 0.1054(5) -0.2240(6) 0.1436(6) C19 C -0.0186(5) -0.0156(5) 0.2116(5) H19A H -0.0685(5) -0.0197(5) 0.1994(5) H19B H -0.0122(5) -0.0378(5) 0.2580(5) N20 N 0.0002(4) 0.0649(4) 0.2147(4) H20N H 0.0505(23) 0.0812(77) 0.2092(74) C21 C -0.0406(5) 0.1193(6) 0.1833(5) O21 O -0.0925(3) 0.1037(4) 0.1471(4) C22 C -0.0174(4) 0.2020(5) 0.1930(4) C23 C 0.0525(4) 0.2220(5) 0.2080(4) H23A H 0.0868(4) 0.1837(5) 0.2117(4) C24 C 0.0717(4) 0.2985(5) 0.2175(4) C25 C 0.0201(5) 0.3551(5) 0.2133(5) H25A H 0.0319(5) 0.4066(5) 0.2202(5) C26 C -0.0488(5) 0.3341(7) 0.1989(5) H26A H -0.0835(5) 0.3720(7) 0.1952(5) C27 C -0.0672(5) 0.2587(6) 0.1900(5) H27A H -0.1145(5) 0.2459(6) 0.1817(5) C28 C 0.1474(4) 0.3239(5) 0.2296(4) O28 O 0.1617(3) 0.3921(4) 0.2310(4) N29 N 0.1964(4) 0.2689(4) 0.2358(4) H29N H 0.1809(29) 0.2158(12) 0.2442(29) C30 C 0.2712(4) 0.2860(6) 0.2505(5) H30A H 0.2805(4) 0.3397(6) 0.2396(5) H30B H 0.2808(4) 0.2783(6) 0.3001(5) C31 C 0.3194(4) 0.2362(5) 0.2086(5) C32 C 0.3400(5) 0.1626(5) 0.2330(4) H32A H 0.3249(5) 0.1454(5) 0.2766(4) C33 C 0.3822(4) 0.1165(5) 0.1924(5) H33A H 0.3957(4) 0.0685(5) 0.2099(5) C34 C 0.4055(4) 0.1380(5) 0.1272(5) C35 C 0.3865(5) 0.2116(6) 0.1035(5) H35A H 0.4024(5) 0.2288(6) 0.0601(5) C36 C 0.3446(5) 0.2588(5) 0.1436(5) H36A H 0.3327(5) 0.3074(5) 0.1266(5) C41 C 0.2262(4) 0.1427(5) -0.0131(4) H41A H 0.2713(4) 0.1620(5) 0.0060(4) S42 S 0.20868(13) 0.05113(14) 0.02917(11) O42 O 0.2728(3) 0.0033(4) 0.0220(3) C43 C 0.2040(5) 0.0830(5) 0.1179(4) H43A H 0.2412(5) 0.1205(5) 0.1267(4) H43B H 0.1587(5) 0.1080(5) 0.1256(4) C44 C 0.2123(4) 0.0158(5) 0.1689(4) H44A H 0.1782(4) -0.0241(5) 0.1573(4) H44B H 0.2595(4) -0.0059(5) 0.1649(4) C45 C 0.2007(4) 0.0426(5) 0.2425(4) O45 O 0.1625(3) 0.0959(3) 0.2582(3) N46 N 0.2349(3) 0.0009(4) 0.2918(3) H46N H 0.2619(31) -0.0459(22) 0.2808(35) C47 C 0.2271(4) 0.0180(5) 0.3654(4) H47A H 0.2348(4) 0.0728(5) 0.3725(4) H47B H 0.2634(4) -0.0094(5) 0.3916(4) C48 C 0.1574(5) -0.0026(5) 0.3937(5) O48 O 0.1079(4) -0.0314(4) 0.3615(3) O49 O 0.1532(3) 0.0155(4) 0.4609(3) C50 C 0.0867(6) 0.0075(8) 0.4946(5) H50A H 0.0663(6) -0.0423(8) 0.4831(5) H50B H 0.0544(6) 0.0471(8) 0.4777(5) C51 C 0.0951(5) 0.0144(6) 0.5728(5) H51A H 0.0467(5) 0.0100(6) 0.5908(5) C52 C 0.1327(6) -0.0504(7) 0.6039(6) C53 C 0.1323(8) -0.1208(10) 0.5718(9) H53A H 0.1106(8) -0.1225(10) 0.5278(9) C54 C 0.1592(12) -0.1881(17) 0.5953(13) H54A H 0.1582(12) -0.2331(17) 0.5688(13) C55 C 0.1881(13) -0.1847(9) 0.6615(16) H55A H 0.2053(13) -0.2302(9) 0.6810(16) C56 C 0.1938(8) -0.1154(13) 0.7029(8) H56A H 0.2152(8) -0.1145(13) 0.7471(8) C57 C 0.1632(6) -0.0464(8) 0.6703(7) H57A H 0.1644(6) 0.0004(8) 0.6942(7) C58 C 0.1181(7) 0.0942(7) 0.5928(5) C59 C 0.1888(7) 0.1185(8) 0.5857(5) H59A H 0.2233(7) 0.0840(8) 0.5709(5) C60 C 0.2064(9) 0.1930(12) 0.6007(6) H60A H 0.2530(9) 0.2098(12) 0.5966(6) C61 C 0.1548(14) 0.2420(9) 0.6217(8) H61A H 0.1673(14) 0.2926(9) 0.6324(8) C62 C 0.0861(11) 0.2209(12) 0.6277(8) H62A H 0.0517(11) 0.2563(12) 0.6413(8) C63 C 0.0685(7) 0.1462(9) 0.6133(5) H63A H 0.0215(7) 0.1305(9) 0.6175(5) C64 C 0.2376(5) 0.1273(5) -0.0907(4) C65 C 0.1866(5) 0.1398(6) -0.1421(5) H65A H 0.1416(5) 0.1563(6) -0.1292(5) C66 C 0.2011(5) 0.1285(6) -0.2101(5) H66A H 0.1666(5) 0.1393(6) -0.2440(5) C67 C 0.2668(6) 0.1010(7) -0.2305(5) H67A H 0.2764(6) 0.0919(7) -0.2776(5) C68 C 0.3184(5) 0.0873(6) -0.1789(5) H68A H 0.3629(5) 0.0686(6) -0.1912(5) C69 C 0.3029(5) 0.1016(5) -0.1111(4) H69A H 0.3378(5) 0.0938(5) -0.0771(4) C70 C 0.1695(4) 0.2025(6) 0.0044(4) C71 C 0.0978(5) 0.1876(6) 0.0035(4) H71A H 0.0819(5) 0.1384(6) -0.0080(4) C72 C 0.0510(6) 0.2421(9) 0.0189(6) H72A H 0.0027(6) 0.2306(9) 0.0182(6) C73 C 0.0729(8) 0.3143(9) 0.0357(6) H73A H 0.0398(8) 0.3523(9) 0.0461(6) C74 C 0.1423(9) 0.3309(7) 0.0373(6) H74A H 0.1575(9) 0.3805(7) 0.0485(6) C75 C 0.1903(6) 0.2752(7) 0.0225(5) H75A H 0.2384(6) 0.2868(7) 0.0248(5) C80 C 0.0875(10) 0.6030(5) 0.0635(4) H80A H 0.1235(10) 0.6396(5) 0.0786(4) H80B H 0.0421(10) 0.6293(5) 0.0620(4) Cl1 Cl 0.1084(5) 0.5667(5) -0.0208(4) Cl2 Cl 0.0841(3) 0.5245(3) 0.1227(3) O90 O -0.0486(5) -0.3044(6) 0.1850(6) O91 O -0.2374(5) 0.0930(6) 0.1060(6) O92 O -0.0835(14) -0.4307(11) 0.2425(14) O93 O -0.1178(16) -0.4504(13) 0.1603(22) #END