Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Volker Boehmer' _publ_contact_author_address ; Fachbereich Chemie, Pharmazie und Geowissenschaften Johannes Gutenberg Universitat Duesbergweg 10-14 Mainz D-55099 GERMANY ; _publ_contact_author_email VBOEHMER@MAIL.UNI-MAINZ.DE _publ_section_title ; Cyclic triureas - synthesis, crystal structures and properties ; loop_ _publ_author_name 'Volker Boehmer' 'Francoise Arnaud-Neu' 'Michael Bolte' 'Veronique Hubscher-Bruder' 'Emilie Jobin' ; D.Meshcheryakov ; 'Iris Thondorf' 'Sabine Werner' data_boeh31 _database_code_depnum_ccdc_archive 'CCDC 667517' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63 H72 Cl6 N6 O6' _chemical_formula_weight 1221.97 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' Cl Cl 0.1484 0.1585 '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' _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 14.2014(19) _cell_length_b 15.4184(19) _cell_length_c 15.7438(17) _cell_angle_alpha 73.389(9) _cell_angle_beta 81.409(10) _cell_angle_gamma 66.041(9) _cell_volume 3016.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13620 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 24.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8957 _exptl_absorpt_correction_T_max 0.9195 _exptl_absorpt_process_details 'MULABS (Spek, 1990; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24329 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.04 _reflns_number_total 10411 _reflns_number_gt 6016 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.2000P)^2^] 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 10411 _refine_ls_number_parameters 728 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.3167 _refine_ls_wR_factor_gt 0.2809 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2542(4) 0.3543(4) 0.8929(3) 0.0346(11) Uani 1 1 d . . . O1 O 0.1766(3) 0.3414(3) 0.9275(3) 0.0616(13) Uani 1 1 d . . . N11 N 0.2715(3) 0.4374(3) 0.8819(3) 0.0333(9) Uani 1 1 d . . . H11 H 0.3326 0.4358 0.8595 0.040 Uiso 1 1 calc R . . N12 N 0.3364(3) 0.2847(3) 0.8605(3) 0.0348(9) Uani 1 1 d . . . H12 H 0.3859 0.3035 0.8321 0.042 Uiso 1 1 calc R . . C2 C 0.5304(3) 0.3478(3) 0.7116(3) 0.0287(10) Uani 1 1 d . . . O2 O 0.4718(3) 0.4166(2) 0.7451(2) 0.0365(8) Uani 1 1 d . . . N21 N 0.6242(3) 0.2870(3) 0.7428(3) 0.0298(8) Uani 1 1 d . . . H21 H 0.6593 0.3111 0.7644 0.036 Uiso 1 1 calc R . . N22 N 0.5005(3) 0.3310(3) 0.6414(3) 0.0278(8) Uani 1 1 d . . . H22 H 0.4358 0.3391 0.6391 0.033 Uiso 1 1 calc R . . C3 C 0.5635(4) 0.6228(3) 0.6955(3) 0.0309(10) Uani 1 1 d . . . O3 O 0.6128(3) 0.6722(3) 0.6932(2) 0.0446(9) Uani 1 1 d . . . N31 N 0.5686(3) 0.5794(3) 0.6292(3) 0.0309(9) Uani 1 1 d . . . H31 H 0.5241 0.5519 0.6329 0.037 Uiso 1 1 calc R . . N32 N 0.4948(3) 0.6065(3) 0.7624(3) 0.0361(9) Uani 1 1 d . . . H32 H 0.4534 0.5813 0.7520 0.043 Uiso 1 1 calc R . . C11 C 0.3511(4) 0.1867(3) 0.8671(3) 0.0307(10) Uani 1 1 d . . . C12 C 0.2785(4) 0.1457(4) 0.8965(3) 0.0350(11) Uani 1 1 d . . . H12A H 0.2113 0.1847 0.9144 0.042 Uiso 1 1 calc R . . C13 C 0.3027(4) 0.0469(4) 0.9004(3) 0.0407(12) Uani 1 1 d . . . C14 C 0.4009(4) -0.0077(4) 0.8716(3) 0.0393(12) Uani 1 1 d . . . H14 H 0.4173 -0.0742 0.8728 0.047 Uiso 1 1 calc R . . C15 C 0.4759(4) 0.0315(3) 0.8409(3) 0.0338(10) Uani 1 1 d . . . C16 C 0.4498(4) 0.1278(3) 0.8388(3) 0.0293(10) Uani 1 1 d . . . O16 O 0.5148(2) 0.1770(2) 0.8103(2) 0.0327(7) Uani 1 1 d . . . C17 C 0.2219(5) 0.0024(4) 0.9355(4) 0.0476(14) Uani 1 1 d . . . C171 C 0.2374(9) -0.0827(9) 0.9056(10) 0.135(6) Uani 1 1 d . . . H17A H 0.2586 -0.0722 0.8425 0.202 Uiso 1 1 calc R . . H17B H 0.1729 -0.0936 0.9139 0.202 Uiso 1 1 calc R . . H17C H 0.2911 -0.1402 0.9399 0.202 Uiso 1 1 calc R . . C172 C 0.2038(16) -0.0067(16) 1.0302(7) 0.218(11) Uani 1 1 d . . . H17D H 0.1941 0.0549 1.0432 0.327 Uiso 1 1 calc R . . H17E H 0.2633 -0.0598 1.0616 0.327 Uiso 1 1 calc R . . H17F H 0.1419 -0.0214 1.0498 0.327 Uiso 1 1 calc R . . C173 C 0.1157(9) 0.0769(9) 0.8945(16) 0.197(10) Uani 1 1 d . . . H17G H 0.0964 0.1391 0.9103 0.295 Uiso 1 1 calc R . . H17H H 0.0626 0.0500 0.9179 0.295 Uiso 1 1 calc R . . H17I H 0.1218 0.0880 0.8298 0.295 Uiso 1 1 calc R . . C18 C 0.5845(4) -0.0311(3) 0.8099(4) 0.0369(11) Uani 1 1 d . . . C181 C 0.6364(5) -0.1171(4) 0.8891(5) 0.0560(15) Uani 1 1 d . . . H18A H 0.5941 -0.1565 0.9105 0.084 Uiso 1 1 calc R . . H18B H 0.6430 -0.0912 0.9370 0.084 Uiso 1 1 calc R . . H18C H 0.7050 -0.1582 0.8700 0.084 Uiso 1 1 calc R . . C182 C 0.5735(5) -0.0716(4) 0.7349(4) 0.0511(14) Uani 1 1 d . . . H18D H 0.5311 -0.1107 0.7565 0.077 Uiso 1 1 calc R . . H18E H 0.6419 -0.1128 0.7156 0.077 Uiso 1 1 calc R . . H18F H 0.5405 -0.0170 0.6848 0.077 Uiso 1 1 calc R . . C21 C 0.6699(3) 0.1856(3) 0.7429(3) 0.0302(10) Uani 1 1 d . . . C22 C 0.7708(4) 0.1429(4) 0.7139(3) 0.0354(11) Uani 1 1 d . . . H22A H 0.8108 0.1818 0.6915 0.042 Uiso 1 1 calc R . . C23 C 0.8148(4) 0.0423(4) 0.7171(3) 0.0368(11) Uani 1 1 d . . . C24 C 0.7525(4) -0.0100(4) 0.7461(3) 0.0391(12) Uani 1 1 d . . . H24 H 0.7808 -0.0772 0.7454 0.047 Uiso 1 1 calc R . . C25 C 0.6494(4) 0.0296(3) 0.7768(3) 0.0339(10) Uani 1 1 d . . . C26 C 0.6114(3) 0.1288(3) 0.7763(3) 0.0312(10) Uani 1 1 d . . . C27 C 0.9298(4) -0.0043(4) 0.6905(4) 0.0446(13) Uani 1 1 d . . . C271 C 0.9910(5) -0.0177(10) 0.7624(7) 0.126(5) Uani 1 1 d . . . H27A H 0.9760 0.0460 0.7737 0.188 Uiso 1 1 calc R . . H27B H 1.0644 -0.0473 0.7461 0.188 Uiso 1 1 calc R . . H27C H 0.9741 -0.0609 0.8159 0.188 Uiso 1 1 calc R . . C272 C 0.9515(7) 0.0597(8) 0.6017(7) 0.100(3) Uani 1 1 d . . . H27D H 0.9070 0.0652 0.5568 0.151 Uiso 1 1 calc R . . H27E H 1.0239 0.0297 0.5829 0.151 Uiso 1 1 calc R . . H27F H 0.9373 0.1251 0.6086 0.151 Uiso 1 1 calc R . . C273 C 0.9569(6) -0.1025(8) 0.6715(9) 0.118(4) Uani 1 1 d . . . H27G H 0.9165 -0.0942 0.6224 0.177 Uiso 1 1 calc R . . H27H H 0.9413 -0.1472 0.7245 0.177 Uiso 1 1 calc R . . H27I H 1.0306 -0.1298 0.6554 0.177 Uiso 1 1 calc R . . C31 C 0.5731(3) 0.2999(3) 0.5704(3) 0.0282(9) Uani 1 1 d . . . C32 C 0.5773(3) 0.2231(3) 0.5398(3) 0.0298(10) Uani 1 1 d . . . H32A H 0.5350 0.1876 0.5675 0.036 Uiso 1 1 calc R . . C33 C 0.6439(3) 0.1971(3) 0.4681(3) 0.0309(10) Uani 1 1 d . . . C34 C 0.7054(4) 0.2501(3) 0.4305(3) 0.0322(10) Uani 1 1 d . . . H34 H 0.7512 0.2326 0.3822 0.039 Uiso 1 1 calc R . . C35 C 0.7031(3) 0.3285(3) 0.4606(3) 0.0288(9) Uani 1 1 d . . . C36 C 0.6344(3) 0.3519(3) 0.5305(3) 0.0268(9) Uani 1 1 d . . . O36 O 0.6227(3) 0.4278(2) 0.5662(2) 0.0329(8) Uani 1 1 d . . . C37 C 0.6528(4) 0.1085(3) 0.4344(3) 0.0351(11) Uani 1 1 d . . . C371 C 0.6814(6) 0.1228(5) 0.3364(4) 0.065(2) Uani 1 1 d . . . H37A H 0.6868 0.0657 0.3174 0.098 Uiso 1 1 calc R . . H37B H 0.7478 0.1303 0.3253 0.098 Uiso 1 1 calc R . . H37C H 0.6282 0.1818 0.3031 0.098 Uiso 1 1 calc R . . C372 C 0.5504(5) 0.0953(5) 0.4480(5) 0.0575(17) Uani 1 1 d . . . H37D H 0.5579 0.0390 0.4266 0.086 Uiso 1 1 calc R . . H37E H 0.4973 0.1545 0.4149 0.086 Uiso 1 1 calc R . . H37F H 0.5303 0.0838 0.5113 0.086 Uiso 1 1 calc R . . C373 C 0.7329(7) 0.0181(5) 0.4880(6) 0.081(3) Uani 1 1 d . . . H37G H 0.7404 -0.0392 0.4683 0.121 Uiso 1 1 calc R . . H37H H 0.7112 0.0090 0.5510 0.121 Uiso 1 1 calc R . . H37I H 0.7991 0.0259 0.4797 0.121 Uiso 1 1 calc R . . C41 C 0.6389(3) 0.5751(3) 0.5554(3) 0.0286(9) Uani 1 1 d . . . C42 C 0.6789(4) 0.6451(3) 0.5148(3) 0.0325(10) Uani 1 1 d . . . H42 H 0.6598 0.7013 0.5371 0.039 Uiso 1 1 calc R . . C43 C 0.7472(3) 0.6347(4) 0.4410(3) 0.0330(10) Uani 1 1 d . . . C44 C 0.7748(4) 0.5515(3) 0.4106(3) 0.0318(10) Uani 1 1 d . . . H44 H 0.8217 0.5439 0.3609 0.038 Uiso 1 1 calc R . . C45 C 0.7368(3) 0.4790(3) 0.4497(3) 0.0296(10) Uani 1 1 d . . . C46 C 0.6677(3) 0.4930(3) 0.5215(3) 0.0278(9) Uani 1 1 d . . . C47 C 0.7882(4) 0.7160(4) 0.3977(4) 0.0402(12) Uani 1 1 d . . . C471 C 0.8480(6) 0.7250(5) 0.4653(5) 0.0658(18) Uani 1 1 d . . . H47A H 0.8739 0.7770 0.4382 0.099 Uiso 1 1 calc R . . H47B H 0.9061 0.6627 0.4847 0.099 Uiso 1 1 calc R . . H47C H 0.8023 0.7409 0.5166 0.099 Uiso 1 1 calc R . . C472 C 0.6975(5) 0.8144(4) 0.3673(4) 0.0506(14) Uani 1 1 d . . . H47D H 0.7240 0.8660 0.3400 0.076 Uiso 1 1 calc R . . H47E H 0.6521 0.8307 0.4186 0.076 Uiso 1 1 calc R . . H47F H 0.6585 0.8090 0.3239 0.076 Uiso 1 1 calc R . . C473 C 0.8585(5) 0.6959(5) 0.3151(5) 0.0600(18) Uani 1 1 d . . . H47G H 0.8827 0.7495 0.2896 0.090 Uiso 1 1 calc R . . H47H H 0.8196 0.6915 0.2711 0.090 Uiso 1 1 calc R . . H47I H 0.9178 0.6340 0.3321 0.090 Uiso 1 1 calc R . . C38 C 0.7754(3) 0.3819(3) 0.4217(3) 0.0296(10) Uani 1 1 d . . . C381 C 0.8830(4) 0.3183(4) 0.4605(4) 0.0407(12) Uani 1 1 d . . . H38A H 0.9101 0.2555 0.4441 0.061 Uiso 1 1 calc R . . H38B H 0.8774 0.3064 0.5252 0.061 Uiso 1 1 calc R . . H38C H 0.9299 0.3526 0.4366 0.061 Uiso 1 1 calc R . . C382 C 0.7842(5) 0.4002(4) 0.3210(3) 0.0414(12) Uani 1 1 d . . . H38D H 0.8088 0.3376 0.3047 0.062 Uiso 1 1 calc R . . H38E H 0.8332 0.4322 0.2973 0.062 Uiso 1 1 calc R . . H38F H 0.7165 0.4426 0.2962 0.062 Uiso 1 1 calc R . . C51 C 0.4836(4) 0.6258(3) 0.8462(3) 0.0308(10) Uani 1 1 d . . . C52 C 0.4054(4) 0.6059(3) 0.9035(3) 0.0327(10) Uani 1 1 d . . . C53 C 0.3939(4) 0.6133(4) 0.9899(4) 0.0398(12) Uani 1 1 d . . . H53 H 0.3420 0.5972 1.0284 0.048 Uiso 1 1 calc R . . C54 C 0.4581(5) 0.6444(4) 1.0201(4) 0.0424(12) Uani 1 1 d . . . H54 H 0.4515 0.6486 1.0799 0.051 Uiso 1 1 calc R . . C55 C 0.5316(4) 0.6691(4) 0.9634(4) 0.0424(12) Uani 1 1 d . . . H55 H 0.5736 0.6934 0.9837 0.051 Uiso 1 1 calc R . . C56 C 0.5457(4) 0.6593(4) 0.8771(3) 0.0377(11) Uani 1 1 d . . . H56 H 0.5979 0.6755 0.8391 0.045 Uiso 1 1 calc R . . O52 O 0.3462(3) 0.5713(3) 0.8693(2) 0.0395(8) Uani 1 1 d . . . C61 C 0.2028(4) 0.5258(3) 0.9021(3) 0.0330(11) Uani 1 1 d . . . C62 C 0.2427(4) 0.5960(4) 0.8955(3) 0.0337(10) Uani 1 1 d . . . C63 C 0.1790(4) 0.6887(4) 0.9085(4) 0.0450(13) Uani 1 1 d . . . H63 H 0.2061 0.7377 0.9007 0.054 Uiso 1 1 calc R . . C64 C 0.0772(4) 0.7078(4) 0.9325(4) 0.0531(15) Uani 1 1 d . . . H64 H 0.0342 0.7700 0.9429 0.064 Uiso 1 1 calc R . . C65 C 0.0364(4) 0.6387(4) 0.9418(4) 0.0512(15) Uani 1 1 d . . . H65 H -0.0342 0.6529 0.9595 0.061 Uiso 1 1 calc R . . C66 C 0.0982(4) 0.5474(4) 0.9255(4) 0.0419(12) Uani 1 1 d . . . H66 H 0.0693 0.5003 0.9303 0.050 Uiso 1 1 calc R . . C1L C 0.8456(8) 0.6257(8) 0.7497(8) 0.106(3) Uani 1 1 d . . . H1L H 0.7835 0.6311 0.7225 0.128 Uiso 1 1 calc R . . Cl11 Cl 0.9514(3) 0.5314(3) 0.7168(4) 0.200(3) Uani 1 1 d . . . Cl12 Cl 0.8264(3) 0.5939(4) 0.8619(3) 0.1639(17) Uani 1 1 d . . . Cl13 Cl 0.8609(4) 0.7297(3) 0.7082(3) 0.1573(16) Uani 1 1 d . . . C2L C 0.8646(11) 0.3425(10) 0.8221(11) 0.145(6) Uani 1 1 d . . . H2L1 H 0.9128 0.3607 0.8470 0.175 Uiso 0.472(9) 1 calc PR A 1 H2L2 H 0.8931 0.3718 0.8558 0.175 Uiso 0.528(9) 1 calc PR A 2 Cl21 Cl 0.8412(4) 0.2376(3) 0.8748(3) 0.0734(17) Uiso 0.472(9) 1 d P A 1 Cl22 Cl 0.7458(6) 0.4280(5) 0.7861(5) 0.122(3) Uiso 0.472(9) 1 d P A 1 Cl23 Cl 0.8794(19) 0.3371(19) 0.6879(16) 0.309(10) Uiso 0.472(9) 1 d P A 1 Cl24 Cl 0.8062(12) 0.4053(11) 0.7218(10) 0.220(6) Uiso 0.528(9) 1 d P A 2 Cl25 Cl 0.754(3) 0.334(3) 0.846(2) 0.441(17) Uiso 0.528(9) 1 d P A 2 Cl26 Cl 0.892(3) 0.237(3) 0.839(3) 0.435(16) Uiso 0.528(9) 1 d P A 2 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 0.033(2) 0.039(3) 0.034(3) -0.014(2) 0.009(2) -0.017(2) O1 0.047(2) 0.050(2) 0.097(4) -0.041(2) 0.040(2) -0.0272(19) N11 0.0257(19) 0.036(2) 0.039(2) -0.0167(17) 0.0135(16) -0.0129(16) N12 0.032(2) 0.034(2) 0.043(2) -0.0155(18) 0.0118(17) -0.0167(17) C2 0.028(2) 0.033(2) 0.029(2) -0.0122(19) 0.0066(18) -0.0151(19) O2 0.0361(18) 0.0363(17) 0.0389(19) -0.0233(15) 0.0108(15) -0.0104(14) N21 0.0280(19) 0.037(2) 0.031(2) -0.0178(16) 0.0033(15) -0.0139(16) N22 0.0200(17) 0.0361(19) 0.030(2) -0.0162(16) 0.0054(15) -0.0101(15) C3 0.031(2) 0.037(2) 0.028(2) -0.0152(19) 0.0040(18) -0.013(2) O3 0.058(2) 0.061(2) 0.037(2) -0.0241(17) 0.0133(17) -0.041(2) N31 0.032(2) 0.036(2) 0.033(2) -0.0181(17) 0.0082(16) -0.0169(16) N32 0.042(2) 0.049(2) 0.033(2) -0.0219(18) 0.0078(18) -0.0276(19) C11 0.035(2) 0.032(2) 0.030(2) -0.0164(19) 0.0062(19) -0.0150(19) C12 0.037(3) 0.043(3) 0.033(3) -0.019(2) 0.008(2) -0.019(2) C13 0.050(3) 0.048(3) 0.034(3) -0.017(2) 0.005(2) -0.027(2) C14 0.051(3) 0.039(3) 0.037(3) -0.017(2) 0.007(2) -0.023(2) C15 0.037(3) 0.036(2) 0.031(3) -0.014(2) 0.001(2) -0.013(2) C16 0.032(2) 0.032(2) 0.026(2) -0.0088(18) 0.0014(18) -0.0139(19) O16 0.0287(16) 0.0311(16) 0.0394(19) -0.0149(14) 0.0101(14) -0.0123(13) C17 0.057(3) 0.059(3) 0.047(3) -0.026(3) 0.016(3) -0.040(3) C171 0.135(9) 0.152(9) 0.208(13) -0.133(10) 0.100(9) -0.122(8) C172 0.37(2) 0.42(3) 0.057(6) -0.061(10) 0.060(10) -0.37(3) C173 0.081(7) 0.100(8) 0.41(3) -0.019(12) -0.020(12) -0.065(7) C18 0.037(3) 0.031(2) 0.040(3) -0.014(2) -0.002(2) -0.006(2) C181 0.054(3) 0.042(3) 0.063(4) 0.005(3) -0.010(3) -0.019(3) C182 0.047(3) 0.055(3) 0.062(4) -0.037(3) 0.006(3) -0.018(3) C21 0.027(2) 0.037(2) 0.026(2) -0.0143(19) 0.0005(18) -0.0081(19) C22 0.028(2) 0.045(3) 0.031(3) -0.015(2) -0.0013(19) -0.008(2) C23 0.028(2) 0.044(3) 0.032(3) -0.015(2) -0.0009(19) -0.004(2) C24 0.039(3) 0.036(2) 0.033(3) -0.016(2) -0.003(2) 0.001(2) C25 0.035(2) 0.036(2) 0.029(2) -0.013(2) -0.0033(19) -0.008(2) C26 0.028(2) 0.033(2) 0.029(2) -0.0129(19) 0.0013(18) -0.0055(18) C27 0.034(3) 0.050(3) 0.042(3) -0.020(2) 0.005(2) -0.004(2) C271 0.027(3) 0.232(13) 0.097(7) -0.094(8) -0.011(4) 0.010(5) C272 0.056(5) 0.120(7) 0.097(7) -0.036(6) 0.024(5) -0.009(5) C273 0.041(4) 0.136(8) 0.200(12) -0.128(9) 0.017(5) -0.007(5) C31 0.024(2) 0.034(2) 0.028(2) -0.0161(19) 0.0014(17) -0.0083(17) C32 0.031(2) 0.034(2) 0.029(2) -0.0137(19) 0.0013(18) -0.0149(19) C33 0.028(2) 0.034(2) 0.034(3) -0.018(2) 0.0011(19) -0.0105(19) C34 0.032(2) 0.037(2) 0.031(2) -0.020(2) 0.0043(19) -0.0112(19) C35 0.029(2) 0.034(2) 0.027(2) -0.0113(18) -0.0005(18) -0.0121(18) C36 0.026(2) 0.029(2) 0.026(2) -0.0118(18) 0.0013(17) -0.0090(17) O36 0.0423(18) 0.0364(16) 0.0296(17) -0.0204(14) 0.0138(14) -0.0216(14) C37 0.039(3) 0.037(2) 0.039(3) -0.022(2) 0.004(2) -0.017(2) C371 0.103(5) 0.070(4) 0.051(4) -0.043(3) 0.030(4) -0.054(4) C372 0.059(4) 0.070(4) 0.072(4) -0.049(3) 0.018(3) -0.039(3) C373 0.093(6) 0.046(3) 0.102(6) -0.039(4) -0.040(5) 0.002(3) C41 0.029(2) 0.033(2) 0.025(2) -0.0125(18) 0.0007(18) -0.0106(18) C42 0.035(2) 0.036(2) 0.030(2) -0.0127(19) 0.0017(19) -0.0137(19) C43 0.024(2) 0.040(2) 0.034(3) -0.012(2) 0.0029(18) -0.0112(19) C44 0.030(2) 0.036(2) 0.030(2) -0.0120(19) 0.0045(18) -0.0125(19) C45 0.029(2) 0.036(2) 0.025(2) -0.0129(19) 0.0031(18) -0.0121(19) C46 0.027(2) 0.033(2) 0.026(2) -0.0103(18) 0.0028(17) -0.0127(18) C47 0.042(3) 0.038(3) 0.043(3) -0.013(2) 0.011(2) -0.020(2) C471 0.067(4) 0.072(4) 0.078(5) -0.009(4) -0.009(3) -0.051(4) C472 0.063(4) 0.041(3) 0.048(3) -0.011(2) 0.009(3) -0.024(3) C473 0.069(4) 0.052(3) 0.062(4) -0.017(3) 0.029(3) -0.035(3) C38 0.030(2) 0.032(2) 0.027(2) -0.0122(18) 0.0062(18) -0.0112(18) C381 0.032(3) 0.038(3) 0.050(3) -0.013(2) 0.004(2) -0.011(2) C382 0.056(3) 0.047(3) 0.029(3) -0.017(2) 0.009(2) -0.025(2) C51 0.037(2) 0.030(2) 0.026(2) -0.0122(18) 0.0038(19) -0.0114(19) C52 0.037(2) 0.028(2) 0.036(3) -0.0179(19) 0.006(2) -0.0111(19) C53 0.045(3) 0.041(3) 0.036(3) -0.019(2) 0.014(2) -0.018(2) C54 0.061(3) 0.037(3) 0.029(3) -0.013(2) 0.002(2) -0.016(2) C55 0.056(3) 0.043(3) 0.036(3) -0.011(2) -0.008(2) -0.023(2) C56 0.047(3) 0.039(2) 0.034(3) -0.011(2) 0.002(2) -0.022(2) O52 0.0349(18) 0.0493(19) 0.047(2) -0.0307(17) 0.0162(15) -0.0218(16) C61 0.030(2) 0.030(2) 0.031(2) -0.0077(19) 0.0103(19) -0.0075(19) C62 0.033(2) 0.040(2) 0.028(2) -0.016(2) 0.0100(19) -0.012(2) C63 0.045(3) 0.035(3) 0.056(3) -0.020(2) 0.008(3) -0.014(2) C64 0.041(3) 0.042(3) 0.066(4) -0.023(3) 0.016(3) -0.005(2) C65 0.032(3) 0.047(3) 0.063(4) -0.017(3) 0.015(3) -0.006(2) C66 0.031(3) 0.039(3) 0.050(3) -0.012(2) 0.012(2) -0.011(2) C1L 0.083(6) 0.101(7) 0.117(8) -0.033(6) 0.008(6) -0.017(5) Cl11 0.145(3) 0.115(2) 0.333(7) -0.101(3) 0.116(4) -0.053(2) Cl12 0.106(2) 0.263(5) 0.114(3) -0.028(3) -0.0118(19) -0.072(3) Cl13 0.188(4) 0.106(2) 0.183(4) -0.064(2) 0.028(3) -0.055(2) C2L 0.115(10) 0.101(8) 0.186(15) 0.017(9) -0.021(9) -0.037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.220(6) . ? C1 N11 1.358(6) . ? C1 N12 1.376(6) . ? N11 C61 1.410(6) . ? N11 H11 0.8800 . ? N12 C11 1.414(6) . ? N12 H12 0.8800 . ? C2 O2 1.252(5) . ? C2 N21 1.347(6) . ? C2 N22 1.365(6) . ? N21 C21 1.429(6) . ? N21 H21 0.8800 . ? N22 C31 1.449(5) . ? N22 H22 0.8800 . ? C3 O3 1.216(6) . ? C3 N32 1.365(6) . ? C3 N31 1.373(6) . ? N31 C41 1.412(6) . ? N31 H31 0.8800 . ? N32 C51 1.408(6) . ? N32 H32 0.8800 . ? C11 C12 1.377(7) . ? C11 C16 1.414(6) . ? C12 C13 1.403(7) . ? C12 H12A 0.9500 . ? C13 C14 1.391(8) . ? C13 C17 1.525(7) . ? C14 C15 1.392(7) . ? C14 H14 0.9500 . ? C15 C16 1.369(7) . ? C15 C18 1.543(7) . ? C16 O16 1.371(6) . ? O16 C26 1.380(5) . ? C17 C171 1.444(10) . ? C17 C172 1.450(12) . ? C17 C173 1.571(15) . ? C171 H17A 0.9800 . ? C171 H17B 0.9800 . ? C171 H17C 0.9800 . ? C172 H17D 0.9800 . ? C172 H17E 0.9800 . ? C172 H17F 0.9800 . ? C173 H17G 0.9800 . ? C173 H17H 0.9800 . ? C173 H17I 0.9800 . ? C18 C25 1.508(7) . ? C18 C182 1.537(8) . ? C18 C181 1.547(8) . ? C181 H18A 0.9800 . ? C181 H18B 0.9800 . ? C181 H18C 0.9800 . ? C182 H18D 0.9800 . ? C182 H18E 0.9800 . ? C182 H18F 0.9800 . ? C21 C22 1.380(6) . ? C21 C26 1.389(7) . ? C22 C23 1.406(7) . ? C22 H22A 0.9500 . ? C23 C24 1.376(8) . ? C23 C27 1.540(7) . ? C24 C25 1.407(7) . ? C24 H24 0.9500 . ? C25 C26 1.399(7) . ? C27 C271 1.447(10) . ? C27 C273 1.510(10) . ? C27 C272 1.533(12) . ? C271 H27A 0.9800 . ? C271 H27B 0.9800 . ? C271 H27C 0.9800 . ? C272 H27D 0.9800 . ? C272 H27E 0.9800 . ? C272 H27F 0.9800 . ? C273 H27G 0.9800 . ? C273 H27H 0.9800 . ? C273 H27I 0.9800 . ? C31 C32 1.378(6) . ? C31 C36 1.382(6) . ? C32 C33 1.401(6) . ? C32 H32A 0.9500 . ? C33 C34 1.391(7) . ? C33 C37 1.554(6) . ? C34 C35 1.406(6) . ? C34 H34 0.9500 . ? C35 C36 1.383(6) . ? C35 C38 1.521(6) . ? C36 O36 1.381(5) . ? O36 C46 1.376(5) . ? C37 C373 1.509(9) . ? C37 C371 1.511(8) . ? C37 C372 1.525(8) . ? C371 H37A 0.9800 . ? C371 H37B 0.9800 . ? C371 H37C 0.9800 . ? C372 H37D 0.9800 . ? C372 H37E 0.9800 . ? C372 H37F 0.9800 . ? C373 H37G 0.9800 . ? C373 H37H 0.9800 . ? C373 H37I 0.9800 . ? C41 C42 1.375(7) . ? C41 C46 1.398(6) . ? C42 C43 1.400(7) . ? C42 H42 0.9500 . ? C43 C44 1.384(7) . ? C43 C47 1.536(7) . ? C44 C45 1.386(7) . ? C44 H44 0.9500 . ? C45 C46 1.387(6) . ? C45 C38 1.542(6) . ? C47 C471 1.524(9) . ? C47 C473 1.540(7) . ? C47 C472 1.540(8) . ? C471 H47A 0.9800 . ? C471 H47B 0.9800 . ? C471 H47C 0.9800 . ? C472 H47D 0.9800 . ? C472 H47E 0.9800 . ? C472 H47F 0.9800 . ? C473 H47G 0.9800 . ? C473 H47H 0.9800 . ? C473 H47I 0.9800 . ? C38 C382 1.523(7) . ? C38 C381 1.547(7) . ? C381 H38A 0.9800 . ? C381 H38B 0.9800 . ? C381 H38C 0.9800 . ? C382 H38D 0.9800 . ? C382 H38E 0.9800 . ? C382 H38F 0.9800 . ? C51 C56 1.387(7) . ? C51 C52 1.400(7) . ? C52 C53 1.377(7) . ? C52 O52 1.394(6) . ? C53 C54 1.379(8) . ? C53 H53 0.9500 . ? C54 C55 1.372(8) . ? C54 H54 0.9500 . ? C55 C56 1.386(8) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? O52 C62 1.389(6) . ? C61 C62 1.386(7) . ? C61 C66 1.400(7) . ? C62 C63 1.402(7) . ? C63 C64 1.368(8) . ? C63 H63 0.9500 . ? C64 C65 1.372(9) . ? C64 H64 0.9500 . ? C65 C66 1.397(8) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C1L Cl13 1.639(12) . ? C1L Cl12 1.704(12) . ? C1L Cl11 1.750(10) . ? C1L H1L 1.0000 . ? C2L Cl26 1.46(4) . ? C2L Cl25 1.62(4) . ? C2L Cl22 1.721(16) . ? C2L Cl24 1.73(2) . ? C2L Cl21 1.732(15) . ? C2L Cl23 2.11(3) . ? C2L H2L1 1.0000 . ? C2L H2L2 1.0000 . ? Cl24 Cl25 2.14(4) . ? Cl25 Cl26 1.94(4) . ? 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 O1 C1 N11 125.2(4) . . ? O1 C1 N12 123.4(4) . . ? N11 C1 N12 111.4(4) . . ? C1 N11 C61 127.5(4) . . ? C1 N11 H11 116.3 . . ? C61 N11 H11 116.3 . . ? C1 N12 C11 127.9(4) . . ? C1 N12 H12 116.1 . . ? C11 N12 H12 116.1 . . ? O2 C2 N21 122.3(4) . . ? O2 C2 N22 120.6(4) . . ? N21 C2 N22 117.1(4) . . ? C2 N21 C21 123.6(4) . . ? C2 N21 H21 118.2 . . ? C21 N21 H21 118.2 . . ? C2 N22 C31 121.4(4) . . ? C2 N22 H22 119.3 . . ? C31 N22 H22 119.3 . . ? O3 C3 N32 124.4(4) . . ? O3 C3 N31 123.5(4) . . ? N32 C3 N31 112.1(4) . . ? C3 N31 C41 125.6(4) . . ? C3 N31 H31 117.2 . . ? C41 N31 H31 117.2 . . ? C3 N32 C51 126.6(4) . . ? C3 N32 H32 116.7 . . ? C51 N32 H32 116.7 . . ? C12 C11 C16 118.6(4) . . ? C12 C11 N12 126.2(4) . . ? C16 C11 N12 115.2(4) . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C14 C13 C12 118.3(5) . . ? C14 C13 C17 121.9(5) . . ? C12 C13 C17 119.8(5) . . ? C13 C14 C15 122.5(5) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C16 C15 C14 117.5(4) . . ? C16 C15 C18 121.2(4) . . ? C14 C15 C18 121.3(4) . . ? C15 C16 O16 124.5(4) . . ? C15 C16 C11 122.3(4) . . ? O16 C16 C11 113.2(4) . . ? C16 O16 C26 118.4(3) . . ? C171 C17 C172 116.2(10) . . ? C171 C17 C13 114.8(5) . . ? C172 C17 C13 110.1(6) . . ? C171 C17 C173 101.6(10) . . ? C172 C17 C173 104.4(13) . . ? C13 C17 C173 108.6(6) . . ? C17 C171 H17A 109.5 . . ? C17 C171 H17B 109.5 . . ? H17A C171 H17B 109.5 . . ? C17 C171 H17C 109.5 . . ? H17A C171 H17C 109.5 . . ? H17B C171 H17C 109.5 . . ? C17 C172 H17D 109.5 . . ? C17 C172 H17E 109.5 . . ? H17D C172 H17E 109.5 . . ? C17 C172 H17F 109.5 . . ? H17D C172 H17F 109.5 . . ? H17E C172 H17F 109.5 . . ? C17 C173 H17G 109.5 . . ? C17 C173 H17H 109.5 . . ? H17G C173 H17H 109.5 . . ? C17 C173 H17I 109.5 . . ? H17G C173 H17I 109.5 . . ? H17H C173 H17I 109.5 . . ? C25 C18 C182 109.6(4) . . ? C25 C18 C15 110.7(4) . . ? C182 C18 C15 108.7(4) . . ? C25 C18 C181 109.6(4) . . ? C182 C18 C181 109.6(5) . . ? C15 C18 C181 108.6(4) . . ? C18 C181 H18A 109.5 . . ? C18 C181 H18B 109.5 . . ? H18A C181 H18B 109.5 . . ? C18 C181 H18C 109.5 . . ? H18A C181 H18C 109.5 . . ? H18B C181 H18C 109.5 . . ? C18 C182 H18D 109.5 . . ? C18 C182 H18E 109.5 . . ? H18D C182 H18E 109.5 . . ? C18 C182 H18F 109.5 . . ? H18D C182 H18F 109.5 . . ? H18E C182 H18F 109.5 . . ? C22 C21 C26 120.0(4) . . ? C22 C21 N21 121.6(4) . . ? C26 C21 N21 118.4(4) . . ? C21 C22 C23 120.5(5) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C24 C23 C22 117.6(4) . . ? C24 C23 C27 123.3(5) . . ? C22 C23 C27 119.1(5) . . ? C23 C24 C25 124.3(5) . . ? C23 C24 H24 117.9 . . ? C25 C24 H24 117.9 . . ? C26 C25 C24 115.5(5) . . ? C26 C25 C18 122.0(4) . . ? C24 C25 C18 122.5(4) . . ? O16 C26 C21 115.1(4) . . ? O16 C26 C25 122.9(4) . . ? C21 C26 C25 122.0(4) . . ? C271 C27 C273 108.7(8) . . ? C271 C27 C272 114.6(8) . . ? C273 C27 C272 104.2(7) . . ? C271 C27 C23 108.7(5) . . ? C273 C27 C23 112.0(5) . . ? C272 C27 C23 108.6(5) . . ? C27 C271 H27A 109.5 . . ? C27 C271 H27B 109.5 . . ? H27A C271 H27B 109.5 . . ? C27 C271 H27C 109.5 . . ? H27A C271 H27C 109.5 . . ? H27B C271 H27C 109.5 . . ? C27 C272 H27D 109.5 . . ? C27 C272 H27E 109.5 . . ? H27D C272 H27E 109.5 . . ? C27 C272 H27F 109.5 . . ? H27D C272 H27F 109.5 . . ? H27E C272 H27F 109.5 . . ? C27 C273 H27G 109.5 . . ? C27 C273 H27H 109.5 . . ? H27G C273 H27H 109.5 . . ? C27 C273 H27I 109.5 . . ? H27G C273 H27I 109.5 . . ? H27H C273 H27I 109.5 . . ? C32 C31 C36 120.3(4) . . ? C32 C31 N22 120.7(4) . . ? C36 C31 N22 119.0(4) . . ? C31 C32 C33 120.2(4) . . ? C31 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? C34 C33 C32 117.9(4) . . ? C34 C33 C37 120.9(4) . . ? C32 C33 C37 121.2(4) . . ? C33 C34 C35 123.2(4) . . ? C33 C34 H34 118.4 . . ? C35 C34 H34 118.4 . . ? C36 C35 C34 116.2(4) . . ? C36 C35 C38 121.6(4) . . ? C34 C35 C38 122.2(4) . . ? O36 C36 C31 115.1(4) . . ? O36 C36 C35 122.7(4) . . ? C31 C36 C35 122.3(4) . . ? C46 O36 C36 118.5(3) . . ? C373 C37 C371 111.1(6) . . ? C373 C37 C372 108.8(6) . . ? C371 C37 C372 107.1(5) . . ? C373 C37 C33 107.5(4) . . ? C371 C37 C33 111.5(4) . . ? C372 C37 C33 110.8(4) . . ? C37 C371 H37A 109.5 . . ? C37 C371 H37B 109.5 . . ? H37A C371 H37B 109.5 . . ? C37 C371 H37C 109.5 . . ? H37A C371 H37C 109.5 . . ? H37B C371 H37C 109.5 . . ? C37 C372 H37D 109.5 . . ? C37 C372 H37E 109.5 . . ? H37D C372 H37E 109.5 . . ? C37 C372 H37F 109.5 . . ? H37D C372 H37F 109.5 . . ? H37E C372 H37F 109.5 . . ? C37 C373 H37G 109.5 . . ? C37 C373 H37H 109.5 . . ? H37G C373 H37H 109.5 . . ? C37 C373 H37I 109.5 . . ? H37G C373 H37I 109.5 . . ? H37H C373 H37I 109.5 . . ? C42 C41 C46 118.7(4) . . ? C42 C41 N31 125.2(4) . . ? C46 C41 N31 116.0(4) . . ? C41 C42 C43 120.9(4) . . ? C41 C42 H42 119.5 . . ? C43 C42 H42 119.5 . . ? C44 C43 C42 118.4(4) . . ? C44 C43 C47 123.0(4) . . ? C42 C43 C47 118.6(4) . . ? C43 C44 C45 122.5(4) . . ? C43 C44 H44 118.7 . . ? C45 C44 H44 118.7 . . ? C44 C45 C46 117.3(4) . . ? C44 C45 C38 122.5(4) . . ? C46 C45 C38 120.0(4) . . ? O36 C46 C45 123.6(4) . . ? O36 C46 C41 114.2(4) . . ? C45 C46 C41 122.1(4) . . ? C471 C47 C43 109.1(5) . . ? C471 C47 C473 109.5(5) . . ? C43 C47 C473 112.2(4) . . ? C471 C47 C472 109.1(5) . . ? C43 C47 C472 109.8(4) . . ? C473 C47 C472 107.1(5) . . ? C47 C471 H47A 109.5 . . ? C47 C471 H47B 109.5 . . ? H47A C471 H47B 109.5 . . ? C47 C471 H47C 109.5 . . ? H47A C471 H47C 109.5 . . ? H47B C471 H47C 109.5 . . ? C47 C472 H47D 109.5 . . ? C47 C472 H47E 109.5 . . ? H47D C472 H47E 109.5 . . ? C47 C472 H47F 109.5 . . ? H47D C472 H47F 109.5 . . ? H47E C472 H47F 109.5 . . ? C47 C473 H47G 109.5 . . ? C47 C473 H47H 109.5 . . ? H47G C473 H47H 109.5 . . ? C47 C473 H47I 109.5 . . ? H47G C473 H47I 109.5 . . ? H47H C473 H47I 109.5 . . ? C35 C38 C382 110.6(4) . . ? C35 C38 C45 109.9(3) . . ? C382 C38 C45 110.9(4) . . ? C35 C38 C381 108.8(4) . . ? C382 C38 C381 109.4(4) . . ? C45 C38 C381 107.1(4) . . ? C38 C381 H38A 109.5 . . ? C38 C381 H38B 109.5 . . ? H38A C381 H38B 109.5 . . ? C38 C381 H38C 109.5 . . ? H38A C381 H38C 109.5 . . ? H38B C381 H38C 109.5 . . ? C38 C382 H38D 109.5 . . ? C38 C382 H38E 109.5 . . ? H38D C382 H38E 109.5 . . ? C38 C382 H38F 109.5 . . ? H38D C382 H38F 109.5 . . ? H38E C382 H38F 109.5 . . ? C56 C51 C52 118.1(4) . . ? C56 C51 N32 125.2(4) . . ? C52 C51 N32 116.6(4) . . ? C53 C52 O52 122.9(4) . . ? C53 C52 C51 121.4(5) . . ? O52 C52 C51 115.6(4) . . ? C52 C53 C54 119.6(5) . . ? C52 C53 H53 120.2 . . ? C54 C53 H53 120.2 . . ? C55 C54 C53 119.7(5) . . ? C55 C54 H54 120.2 . . ? C53 C54 H54 120.2 . . ? C54 C55 C56 121.1(5) . . ? C54 C55 H55 119.4 . . ? C56 C55 H55 119.4 . . ? C55 C56 C51 120.0(5) . . ? C55 C56 H56 120.0 . . ? C51 C56 H56 120.0 . . ? C62 O52 C52 119.2(3) . . ? C62 C61 C66 118.9(4) . . ? C62 C61 N11 116.6(4) . . ? C66 C61 N11 124.5(5) . . ? C61 C62 O52 116.2(4) . . ? C61 C62 C63 120.8(5) . . ? O52 C62 C63 122.8(5) . . ? C64 C63 C62 119.2(5) . . ? C64 C63 H63 120.4 . . ? C62 C63 H63 120.4 . . ? C63 C64 C65 121.1(5) . . ? C63 C64 H64 119.5 . . ? C65 C64 H64 119.5 . . ? C64 C65 C66 120.3(5) . . ? C64 C65 H65 119.9 . . ? C66 C65 H65 119.9 . . ? C65 C66 C61 119.6(5) . . ? C65 C66 H66 120.2 . . ? C61 C66 H66 120.2 . . ? Cl13 C1L Cl12 116.3(7) . . ? Cl13 C1L Cl11 109.2(6) . . ? Cl12 C1L Cl11 109.5(7) . . ? Cl13 C1L H1L 107.1 . . ? Cl12 C1L H1L 107.1 . . ? Cl11 C1L H1L 107.1 . . ? Cl26 C2L Cl25 77.7(19) . . ? Cl26 C2L Cl22 122.8(19) . . ? Cl25 C2L Cl22 51.8(14) . . ? Cl26 C2L Cl24 112(2) . . ? Cl25 C2L Cl24 79.7(15) . . ? Cl22 C2L Cl24 42.8(6) . . ? Cl26 C2L Cl21 29.2(16) . . ? Cl25 C2L Cl21 52.9(13) . . ? Cl22 C2L Cl21 104.0(8) . . ? Cl24 C2L Cl21 114.7(11) . . ? Cl26 C2L Cl23 83.0(18) . . ? Cl25 C2L Cl23 98.2(16) . . ? Cl22 C2L Cl23 80.0(10) . . ? Cl24 C2L Cl23 38.5(8) . . ? Cl21 C2L Cl23 101.4(11) . . ? Cl26 C2L H2L1 114.6 . . ? Cl25 C2L H2L1 139.4 . . ? Cl22 C2L H2L1 121.0 . . ? Cl24 C2L H2L1 124.1 . . ? Cl21 C2L H2L1 121.0 . . ? Cl23 C2L H2L1 121.0 . . ? Cl26 C2L H2L2 123.3 . . ? Cl25 C2L H2L2 123.3 . . ? Cl22 C2L H2L2 107.6 . . ? Cl24 C2L H2L2 123.3 . . ? Cl21 C2L H2L2 120.0 . . ? Cl23 C2L H2L2 133.2 . . ? H2L1 C2L H2L2 17.3 . . ? C2L Cl24 Cl25 47.9(11) . . ? C2L Cl25 Cl26 47.6(14) . . ? C2L Cl25 Cl24 52.4(12) . . ? Cl26 Cl25 Cl24 80.5(17) . . ? C2L Cl26 Cl25 54.7(17) . . ? 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 O1 C1 N11 C61 -4.4(9) . . . . ? N12 C1 N11 C61 176.0(5) . . . . ? O1 C1 N12 C11 -5.9(9) . . . . ? N11 C1 N12 C11 173.7(5) . . . . ? O2 C2 N21 C21 146.1(4) . . . . ? N22 C2 N21 C21 -33.3(6) . . . . ? O2 C2 N22 C31 142.6(4) . . . . ? N21 C2 N22 C31 -38.0(6) . . . . ? O3 C3 N31 C41 8.2(8) . . . . ? N32 C3 N31 C41 -173.7(4) . . . . ? O3 C3 N32 C51 -13.5(8) . . . . ? N31 C3 N32 C51 168.4(4) . . . . ? C1 N12 C11 C12 10.2(9) . . . . ? C1 N12 C11 C16 -171.1(5) . . . . ? C16 C11 C12 C13 1.6(8) . . . . ? N12 C11 C12 C13 -179.8(5) . . . . ? C11 C12 C13 C14 -1.7(8) . . . . ? C11 C12 C13 C17 178.4(5) . . . . ? C12 C13 C14 C15 1.3(8) . . . . ? C17 C13 C14 C15 -178.8(5) . . . . ? C13 C14 C15 C16 -0.7(8) . . . . ? C13 C14 C15 C18 179.6(5) . . . . ? C14 C15 C16 O16 -179.9(5) . . . . ? C18 C15 C16 O16 -0.2(8) . . . . ? C14 C15 C16 C11 0.6(7) . . . . ? C18 C15 C16 C11 -179.7(5) . . . . ? C12 C11 C16 C15 -1.0(7) . . . . ? N12 C11 C16 C15 -179.8(5) . . . . ? C12 C11 C16 O16 179.4(4) . . . . ? N12 C11 C16 O16 0.6(6) . . . . ? C15 C16 O16 C26 4.1(7) . . . . ? C11 C16 O16 C26 -176.4(4) . . . . ? C14 C13 C17 C171 -23.2(11) . . . . ? C12 C13 C17 C171 156.7(9) . . . . ? C14 C13 C17 C172 110.1(12) . . . . ? C12 C13 C17 C172 -69.9(12) . . . . ? C14 C13 C17 C173 -136.1(10) . . . . ? C12 C13 C17 C173 43.8(11) . . . . ? C16 C15 C18 C25 -1.8(7) . . . . ? C14 C15 C18 C25 177.9(5) . . . . ? C16 C15 C18 C182 -122.3(5) . . . . ? C14 C15 C18 C182 57.4(6) . . . . ? C16 C15 C18 C181 118.6(5) . . . . ? C14 C15 C18 C181 -61.7(6) . . . . ? C2 N21 C21 C22 133.3(5) . . . . ? C2 N21 C21 C26 -49.1(6) . . . . ? C26 C21 C22 C23 0.5(7) . . . . ? N21 C21 C22 C23 178.1(4) . . . . ? C21 C22 C23 C24 2.9(7) . . . . ? C21 C22 C23 C27 -175.7(5) . . . . ? C22 C23 C24 C25 -3.3(8) . . . . ? C27 C23 C24 C25 175.2(5) . . . . ? C23 C24 C25 C26 0.2(8) . . . . ? C23 C24 C25 C18 -178.6(5) . . . . ? C182 C18 C25 C26 120.0(5) . . . . ? C15 C18 C25 C26 0.1(7) . . . . ? C181 C18 C25 C26 -119.8(5) . . . . ? C182 C18 C25 C24 -61.3(6) . . . . ? C15 C18 C25 C24 178.8(5) . . . . ? C181 C18 C25 C24 59.0(6) . . . . ? C16 O16 C26 C21 175.5(4) . . . . ? C16 O16 C26 C25 -5.9(7) . . . . ? C22 C21 C26 O16 174.7(4) . . . . ? N21 C21 C26 O16 -3.0(6) . . . . ? C22 C21 C26 C25 -3.9(7) . . . . ? N21 C21 C26 C25 178.4(4) . . . . ? C24 C25 C26 O16 -175.0(4) . . . . ? C18 C25 C26 O16 3.9(8) . . . . ? C24 C25 C26 C21 3.5(7) . . . . ? C18 C25 C26 C21 -177.7(5) . . . . ? C24 C23 C27 C271 -101.9(9) . . . . ? C22 C23 C27 C271 76.7(9) . . . . ? C24 C23 C27 C273 18.3(9) . . . . ? C22 C23 C27 C273 -163.1(7) . . . . ? C24 C23 C27 C272 132.8(7) . . . . ? C22 C23 C27 C272 -48.6(8) . . . . ? C2 N22 C31 C32 133.0(5) . . . . ? C2 N22 C31 C36 -50.3(6) . . . . ? C36 C31 C32 C33 0.0(7) . . . . ? N22 C31 C32 C33 176.6(4) . . . . ? C31 C32 C33 C34 0.9(7) . . . . ? C31 C32 C33 C37 177.9(4) . . . . ? C32 C33 C34 C35 -0.5(7) . . . . ? C37 C33 C34 C35 -177.6(4) . . . . ? C33 C34 C35 C36 -0.7(7) . . . . ? C33 C34 C35 C38 176.6(5) . . . . ? C32 C31 C36 O36 179.4(4) . . . . ? N22 C31 C36 O36 2.7(6) . . . . ? C32 C31 C36 C35 -1.4(7) . . . . ? N22 C31 C36 C35 -178.0(4) . . . . ? C34 C35 C36 O36 -179.1(4) . . . . ? C38 C35 C36 O36 3.5(7) . . . . ? C34 C35 C36 C31 1.7(7) . . . . ? C38 C35 C36 C31 -175.7(4) . . . . ? C31 C36 O36 C46 -169.3(4) . . . . ? C35 C36 O36 C46 11.4(6) . . . . ? C34 C33 C37 C373 89.9(7) . . . . ? C32 C33 C37 C373 -87.1(7) . . . . ? C34 C33 C37 C371 -32.1(7) . . . . ? C32 C33 C37 C371 151.0(5) . . . . ? C34 C33 C37 C372 -151.4(5) . . . . ? C32 C33 C37 C372 31.7(7) . . . . ? C3 N31 C41 C42 -31.7(7) . . . . ? C3 N31 C41 C46 149.4(4) . . . . ? C46 C41 C42 C43 -0.2(7) . . . . ? N31 C41 C42 C43 -179.1(5) . . . . ? C41 C42 C43 C44 -0.8(7) . . . . ? C41 C42 C43 C47 179.2(5) . . . . ? C42 C43 C44 C45 0.6(7) . . . . ? C47 C43 C44 C45 -179.5(5) . . . . ? C43 C44 C45 C46 0.7(7) . . . . ? C43 C44 C45 C38 -173.9(5) . . . . ? C36 O36 C46 C45 -10.0(7) . . . . ? C36 O36 C46 C41 170.9(4) . . . . ? C44 C45 C46 O36 179.2(4) . . . . ? C38 C45 C46 O36 -6.0(7) . . . . ? C44 C45 C46 C41 -1.8(7) . . . . ? C38 C45 C46 C41 173.0(4) . . . . ? C42 C41 C46 O36 -179.3(4) . . . . ? N31 C41 C46 O36 -0.4(6) . . . . ? C42 C41 C46 C45 1.5(7) . . . . ? N31 C41 C46 C45 -179.5(4) . . . . ? C44 C43 C47 C471 -118.9(6) . . . . ? C42 C43 C47 C471 61.1(6) . . . . ? C44 C43 C47 C473 2.6(7) . . . . ? C42 C43 C47 C473 -177.4(5) . . . . ? C44 C43 C47 C472 121.7(5) . . . . ? C42 C43 C47 C472 -58.4(6) . . . . ? C36 C35 C38 C382 -140.3(5) . . . . ? C34 C35 C38 C382 42.5(6) . . . . ? C36 C35 C38 C45 -17.5(6) . . . . ? C34 C35 C38 C45 165.3(4) . . . . ? C36 C35 C38 C381 99.5(5) . . . . ? C34 C35 C38 C381 -77.7(6) . . . . ? C44 C45 C38 C35 -167.0(4) . . . . ? C46 C45 C38 C35 18.5(6) . . . . ? C44 C45 C38 C382 -44.3(6) . . . . ? C46 C45 C38 C382 141.2(5) . . . . ? C44 C45 C38 C381 75.0(6) . . . . ? C46 C45 C38 C381 -99.5(5) . . . . ? C3 N32 C51 C56 -4.4(8) . . . . ? C3 N32 C51 C52 178.1(5) . . . . ? C56 C51 C52 C53 -3.9(7) . . . . ? N32 C51 C52 C53 173.8(4) . . . . ? C56 C51 C52 O52 -179.2(4) . . . . ? N32 C51 C52 O52 -1.6(6) . . . . ? O52 C52 C53 C54 177.3(5) . . . . ? C51 C52 C53 C54 2.3(7) . . . . ? C52 C53 C54 C55 1.1(8) . . . . ? C53 C54 C55 C56 -2.9(8) . . . . ? C54 C55 C56 C51 1.3(8) . . . . ? C52 C51 C56 C55 2.0(7) . . . . ? N32 C51 C56 C55 -175.4(5) . . . . ? C53 C52 O52 C62 37.7(7) . . . . ? C51 C52 O52 C62 -147.0(4) . . . . ? C1 N11 C61 C62 171.9(5) . . . . ? C1 N11 C61 C66 -9.9(8) . . . . ? C66 C61 C62 O52 -178.1(5) . . . . ? N11 C61 C62 O52 0.3(7) . . . . ? C66 C61 C62 C63 -2.6(8) . . . . ? N11 C61 C62 C63 175.7(5) . . . . ? C52 O52 C62 C61 -146.2(5) . . . . ? C52 O52 C62 C63 38.4(7) . . . . ? C61 C62 C63 C64 3.5(9) . . . . ? O52 C62 C63 C64 178.6(5) . . . . ? C62 C63 C64 C65 -1.6(10) . . . . ? C63 C64 C65 C66 -1.0(10) . . . . ? C64 C65 C66 C61 1.9(10) . . . . ? C62 C61 C66 C65 0.0(8) . . . . ? N11 C61 C66 C65 -178.2(5) . . . . ? Cl26 C2L Cl24 Cl25 72(2) . . . . ? Cl22 C2L Cl24 Cl25 -43.3(14) . . . . ? Cl21 C2L Cl24 Cl25 40.6(13) . . . . ? Cl23 C2L Cl24 Cl25 117.5(18) . . . . ? Cl22 C2L Cl25 Cl26 151(2) . . . . ? Cl24 C2L Cl25 Cl26 114.9(19) . . . . ? Cl21 C2L Cl25 Cl26 -17.2(17) . . . . ? Cl23 C2L Cl25 Cl26 81.0(18) . . . . ? Cl26 C2L Cl25 Cl24 -114.9(19) . . . . ? Cl22 C2L Cl25 Cl24 36.3(10) . . . . ? Cl21 C2L Cl25 Cl24 -132.1(13) . . . . ? Cl23 C2L Cl25 Cl24 -33.9(9) . . . . ? C2L Cl24 Cl25 Cl26 -42.8(14) . . . . ? Cl22 C2L Cl26 Cl25 -27(2) . . . . ? Cl24 C2L Cl26 Cl25 -73.6(18) . . . . ? Cl21 C2L Cl26 Cl25 29(3) . . . . ? Cl23 C2L Cl26 Cl25 -100.0(16) . . . . ? Cl24 Cl25 Cl26 C2L 46.8(15) . . . . ? 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 N11 H11 O2 0.88 2.45 3.264(5) 154.0 . N12 H12 O2 0.88 2.50 3.339(5) 158.7 . N21 H21 Cl22 0.88 2.67 3.524(8) 162.7 . N21 H21 Cl25 0.88 2.17 3.03(4) 164.3 . N31 H31 O2 0.88 2.60 3.310(5) 137.8 . N32 H32 O2 0.88 2.48 3.165(5) 135.3 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.978 _refine_diff_density_min -0.933 _refine_diff_density_rms 0.112 data_boeh57 _database_code_depnum_ccdc_archive 'CCDC 667518' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H66 Cl N7 O6' _chemical_formula_weight 956.60 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 21.9730(16) _cell_length_b 14.2644(6) _cell_length_c 16.7013(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.085(6) _cell_angle_gamma 90.00 _cell_volume 5205.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 31622 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.1 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2040 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 66076 _diffrn_reflns_av_R_equivalents 0.0866 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.68 _reflns_number_total 9795 _reflns_number_gt 6649 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0545P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9795 _refine_ls_number_parameters 666 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.24996(2) 0.24956(3) 0.62185(3) 0.02627(12) Uani 1 1 d . . . C1 C 0.10837(8) 0.41660(14) 0.61932(11) 0.0239(4) Uani 1 1 d . . . O1 O 0.06428(6) 0.46936(10) 0.61619(9) 0.0338(3) Uani 1 1 d . . . N11 N 0.16681(7) 0.44117(12) 0.65099(10) 0.0251(4) Uani 1 1 d . . . H11 H 0.1971(11) 0.4010(16) 0.6430(13) 0.035(6) Uiso 1 1 d . . . N12 N 0.10629(8) 0.32643(13) 0.59061(12) 0.0321(4) Uani 1 1 d . . . H12 H 0.1348(13) 0.288(2) 0.6062(16) 0.057(8) Uiso 1 1 d . . . C11 C 0.05136(9) 0.27895(15) 0.56221(12) 0.0288(5) Uani 1 1 d . . . C12 C 0.04149(8) 0.18893(15) 0.59150(12) 0.0288(5) Uani 1 1 d . . . C13 C -0.00967(9) 0.13710(17) 0.56293(13) 0.0368(5) Uani 1 1 d . . . H13 H -0.0155 0.0755 0.5824 0.044 Uiso 1 1 calc R . . C14 C -0.05240(10) 0.17701(19) 0.50506(14) 0.0437(6) Uani 1 1 d . . . H14 H -0.0879 0.1427 0.4855 0.052 Uiso 1 1 calc R . . C15 C -0.04344(10) 0.26598(19) 0.47609(14) 0.0438(6) Uani 1 1 d . . . H15 H -0.0729 0.2925 0.4368 0.053 Uiso 1 1 calc R . . C16 C 0.00849(9) 0.31720(17) 0.50396(14) 0.0366(5) Uani 1 1 d . . . H16 H 0.0146 0.3781 0.4833 0.044 Uiso 1 1 calc R . . O12 O 0.08748(6) 0.15680(10) 0.65023(9) 0.0325(3) Uani 1 1 d . . . C21 C 0.12583(8) -0.00042(15) 0.65536(11) 0.0272(5) Uani 1 1 d . . . C22 C 0.08338(9) 0.06452(15) 0.67801(12) 0.0290(5) Uani 1 1 d . . . C23 C 0.04088(9) 0.04001(18) 0.73084(14) 0.0402(6) Uani 1 1 d . . . H23 H 0.0137 0.0859 0.7479 0.048 Uiso 1 1 calc R . . C24 C 0.03851(10) -0.05127(19) 0.75836(14) 0.0435(6) Uani 1 1 d . . . H24 H 0.0095 -0.0685 0.7941 0.052 Uiso 1 1 calc R . . C25 C 0.07876(10) -0.11749(18) 0.73336(13) 0.0399(6) Uani 1 1 d . . . H25 H 0.0761 -0.1807 0.7507 0.048 Uiso 1 1 calc R . . C26 C 0.12311(9) -0.09278(16) 0.68322(12) 0.0333(5) Uani 1 1 d . . . H26 H 0.1513 -0.1383 0.6681 0.040 Uiso 1 1 calc R . . C2 C 0.21277(8) -0.01987(15) 0.57091(11) 0.0263(4) Uani 1 1 d . . . O2 O 0.20847(7) -0.10448(11) 0.56019(10) 0.0419(4) Uani 1 1 d . . . N21 N 0.17102(7) 0.03334(14) 0.60809(10) 0.0284(4) Uani 1 1 d . . . H21 H 0.1750(10) 0.0949(17) 0.6086(13) 0.033(6) Uiso 1 1 d . . . N22 N 0.25913(7) 0.03495(13) 0.54678(10) 0.0273(4) Uani 1 1 d . . . H22 H 0.2630(11) 0.0905(19) 0.5675(15) 0.045(7) Uiso 1 1 d . . . C31 C 0.31017(8) -0.00396(14) 0.51274(11) 0.0243(4) Uani 1 1 d . . . C32 C 0.36920(8) 0.01618(13) 0.54845(11) 0.0229(4) Uani 1 1 d . . . C33 C 0.42024(9) -0.01879(15) 0.51628(12) 0.0287(5) Uani 1 1 d . . . H33 H 0.4601 -0.0048 0.5410 0.034 Uiso 1 1 calc R . . C34 C 0.41266(10) -0.07472(15) 0.44739(13) 0.0330(5) Uani 1 1 d . . . H34 H 0.4474 -0.0994 0.4253 0.040 Uiso 1 1 calc R . . C35 C 0.35435(10) -0.09417(16) 0.41134(13) 0.0347(5) Uani 1 1 d . . . H35 H 0.3492 -0.1321 0.3643 0.042 Uiso 1 1 calc R . . C36 C 0.30324(9) -0.05859(15) 0.44351(13) 0.0323(5) Uani 1 1 d . . . H36 H 0.2634 -0.0717 0.4180 0.039 Uiso 1 1 calc R . . O32 O 0.37140(6) 0.07431(10) 0.61596(8) 0.0292(3) Uani 1 1 d . . . C41 C 0.44384(8) 0.18640(15) 0.67237(11) 0.0260(4) Uani 1 1 d . . . C42 C 0.42768(8) 0.09205(15) 0.66090(11) 0.0268(4) Uani 1 1 d . . . C43 C 0.46345(9) 0.02051(17) 0.69728(13) 0.0360(5) Uani 1 1 d . . . H43 H 0.4512 -0.0430 0.6897 0.043 Uiso 1 1 calc R . . C44 C 0.51735(10) 0.04273(18) 0.74494(13) 0.0417(6) Uani 1 1 d . . . H44 H 0.5422 -0.0057 0.7701 0.050 Uiso 1 1 calc R . . C45 C 0.53464(10) 0.13545(18) 0.75556(13) 0.0388(6) Uani 1 1 d . . . H45 H 0.5718 0.1503 0.7875 0.047 Uiso 1 1 calc R . . C46 C 0.49864(9) 0.20693(17) 0.72042(12) 0.0341(5) Uani 1 1 d . . . H46 H 0.5110 0.2703 0.7288 0.041 Uiso 1 1 calc R . . C3 C 0.41820(9) 0.34515(15) 0.61992(11) 0.0268(4) Uani 1 1 d . . . O3 O 0.47120(6) 0.37059(11) 0.61637(9) 0.0366(4) Uani 1 1 d . . . N31 N 0.40242(7) 0.25560(13) 0.64021(10) 0.0289(4) Uani 1 1 d . . . H31 H 0.3646(12) 0.2388(18) 0.6322(15) 0.050(7) Uiso 1 1 d . . . N32 N 0.36791(8) 0.40282(12) 0.60417(10) 0.0288(4) Uani 1 1 d . . . H32 H 0.3331(11) 0.3830(16) 0.6145(13) 0.039(6) Uiso 1 1 d . . . C51 C 0.36904(9) 0.49710(14) 0.57833(11) 0.0264(4) Uani 1 1 d . . . C52 C 0.32145(8) 0.55604(15) 0.59639(11) 0.0260(4) Uani 1 1 d . . . C53 C 0.31751(9) 0.64817(16) 0.56942(13) 0.0342(5) Uani 1 1 d . . . H53 H 0.2841 0.6867 0.5804 0.041 Uiso 1 1 calc R . . C54 C 0.36340(10) 0.68321(19) 0.52596(14) 0.0437(6) Uani 1 1 d . . . H54 H 0.3618 0.7466 0.5084 0.052 Uiso 1 1 calc R . . C55 C 0.41095(10) 0.62641(18) 0.50838(13) 0.0421(6) Uani 1 1 d . . . H55 H 0.4421 0.6510 0.4790 0.050 Uiso 1 1 calc R . . C56 C 0.41374(9) 0.53355(18) 0.53330(13) 0.0367(5) Uani 1 1 d . . . H56 H 0.4462 0.4946 0.5197 0.044 Uiso 1 1 calc R . . O52 O 0.27689(6) 0.51237(10) 0.63793(9) 0.0307(3) Uani 1 1 d . . . C61 C 0.18234(8) 0.52599(13) 0.69181(11) 0.0225(4) Uani 1 1 d . . . C62 C 0.24043(8) 0.56420(14) 0.68568(11) 0.0239(4) Uani 1 1 d . . . C63 C 0.26038(9) 0.64288(14) 0.72917(12) 0.0304(5) Uani 1 1 d . . . H63 H 0.3003 0.6670 0.7255 0.037 Uiso 1 1 calc R . . C64 C 0.22152(10) 0.68650(15) 0.77849(13) 0.0346(5) Uani 1 1 d . . . H64 H 0.2347 0.7410 0.8081 0.042 Uiso 1 1 calc R . . C65 C 0.16347(10) 0.65030(15) 0.78427(13) 0.0348(5) Uani 1 1 d . . . H65 H 0.1370 0.6803 0.8177 0.042 Uiso 1 1 calc R . . C66 C 0.14395(9) 0.57019(14) 0.74134(13) 0.0305(5) Uani 1 1 d . . . H66 H 0.1043 0.5456 0.7458 0.037 Uiso 1 1 calc R . . N1 N 0.24462(7) 0.36837(11) 0.36861(9) 0.0271(4) Uani 1 1 d . . . C71 C 0.19715(9) 0.29878(14) 0.33059(12) 0.0282(5) Uani 1 1 d . . . H71A H 0.1610 0.3345 0.3068 0.034 Uiso 1 1 calc R . . H71B H 0.2147 0.2661 0.2860 0.034 Uiso 1 1 calc R . . C72 C 0.17557(10) 0.22518(15) 0.38746(13) 0.0359(5) Uani 1 1 d . . . H72A H 0.2096 0.1817 0.4045 0.043 Uiso 1 1 calc R . . H72B H 0.1630 0.2562 0.4361 0.043 Uiso 1 1 calc R . . C73 C 0.12203(12) 0.17063(18) 0.34589(14) 0.0462(6) Uani 1 1 d . . . H73A H 0.0879 0.2145 0.3303 0.055 Uiso 1 1 calc R . . H73B H 0.1345 0.1423 0.2960 0.055 Uiso 1 1 calc R . . C74 C 0.09953(12) 0.09383(19) 0.39817(14) 0.0502(7) Uani 1 1 d . . . H74A H 0.0648 0.0615 0.3685 0.075 Uiso 1 1 calc R . . H74B H 0.0866 0.1215 0.4473 0.075 Uiso 1 1 calc R . . H74C H 0.1327 0.0489 0.4124 0.075 Uiso 1 1 calc R . . C81 C 0.21874(10) 0.42466(15) 0.43523(12) 0.0322(5) Uani 1 1 d . . . H81A H 0.2160 0.3829 0.4821 0.039 Uiso 1 1 calc R . . H81B H 0.2480 0.4754 0.4526 0.039 Uiso 1 1 calc R . . C82 C 0.15594(10) 0.46832(16) 0.41217(14) 0.0377(5) Uani 1 1 d . . . H82A H 0.1239 0.4222 0.4219 0.045 Uiso 1 1 calc R . . H82B H 0.1515 0.4833 0.3540 0.045 Uiso 1 1 calc R . . C83 C 0.14640(13) 0.55780(17) 0.46010(15) 0.0472(6) Uani 1 1 d . . . H83A H 0.1021 0.5719 0.4564 0.057 Uiso 1 1 calc R . . H83B H 0.1609 0.5467 0.5175 0.057 Uiso 1 1 calc R . . C84 C 0.17978(12) 0.64222(17) 0.43049(15) 0.0485(6) Uani 1 1 d . . . H84A H 0.1716 0.6973 0.4627 0.073 Uiso 1 1 calc R . . H84B H 0.1654 0.6541 0.3738 0.073 Uiso 1 1 calc R . . H84C H 0.2239 0.6297 0.4358 0.073 Uiso 1 1 calc R . . C91 C 0.26076(9) 0.43388(15) 0.30141(11) 0.0274(4) Uani 1 1 d . . . H91A H 0.2725 0.3949 0.2564 0.033 Uiso 1 1 calc R . . H91B H 0.2235 0.4692 0.2812 0.033 Uiso 1 1 calc R . . C92 C 0.31189(10) 0.50404(15) 0.32406(12) 0.0320(5) Uani 1 1 d . . . H92A H 0.3515 0.4706 0.3334 0.038 Uiso 1 1 calc R . . H92B H 0.3045 0.5365 0.3745 0.038 Uiso 1 1 calc R . . C93 C 0.31474(9) 0.57588(14) 0.25685(12) 0.0294(5) Uani 1 1 d . . . H93A H 0.2742 0.6062 0.2454 0.035 Uiso 1 1 calc R . . H93B H 0.3243 0.5434 0.2073 0.035 Uiso 1 1 calc R . . C94 C 0.36325(10) 0.65100(16) 0.27939(15) 0.0394(5) Uani 1 1 d . . . H94A H 0.3634 0.6962 0.2352 0.059 Uiso 1 1 calc R . . H94B H 0.4036 0.6214 0.2891 0.059 Uiso 1 1 calc R . . H94C H 0.3539 0.6835 0.3283 0.059 Uiso 1 1 calc R . . C101 C 0.30171(10) 0.31753(16) 0.40664(14) 0.0391(6) Uani 1 1 d D A . H10A H 0.3307 0.3648 0.4319 0.047 Uiso 1 1 calc R . . H10B H 0.2897 0.2764 0.4501 0.047 Uiso 1 1 calc R . . C102 C 0.33506(11) 0.25835(18) 0.34909(19) 0.0569(7) Uani 1 1 d D . . H10C H 0.3034 0.2204 0.3173 0.068 Uiso 0.551(8) 1 calc PR A 1 H10D H 0.3513 0.3026 0.3109 0.068 Uiso 0.551(8) 1 calc PR A 1 H10E H 0.3473 0.2956 0.3034 0.068 Uiso 0.449(8) 1 calc PR A 2 H10F H 0.3105 0.2036 0.3285 0.068 Uiso 0.449(8) 1 calc PR A 2 C103 C 0.3870(3) 0.1919(4) 0.3767(4) 0.0493(19) Uani 0.551(8) 1 d PD A 1 H10G H 0.3720 0.1425 0.4114 0.059 Uiso 0.551(8) 1 calc PR A 1 H10H H 0.4020 0.1612 0.3294 0.059 Uiso 0.551(8) 1 calc PR A 1 C104 C 0.4381(3) 0.2447(4) 0.4228(3) 0.0601(18) Uani 0.551(8) 1 d PD A 1 H10I H 0.4684 0.2003 0.4478 0.090 Uiso 0.551(8) 1 calc PR A 1 H10J H 0.4218 0.2825 0.4647 0.090 Uiso 0.551(8) 1 calc PR A 1 H10K H 0.4575 0.2859 0.3860 0.090 Uiso 0.551(8) 1 calc PR A 1 C105 C 0.3918(3) 0.2288(6) 0.4094(5) 0.049(2) Uani 0.449(8) 1 d PD A 2 H10L H 0.4174 0.2842 0.4252 0.059 Uiso 0.449(8) 1 calc PR A 2 H10M H 0.3779 0.2008 0.4586 0.059 Uiso 0.449(8) 1 calc PR A 2 C106 C 0.4282(4) 0.1576(5) 0.3666(4) 0.074(3) Uani 0.449(8) 1 d PD A 2 H10N H 0.4600 0.1301 0.4051 0.111 Uiso 0.449(8) 1 calc PR A 2 H10O H 0.4474 0.1888 0.3234 0.111 Uiso 0.449(8) 1 calc PR A 2 H10P H 0.4008 0.1081 0.3437 0.111 Uiso 0.449(8) 1 calc PR A 2 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 Cl1 0.0182(2) 0.0270(2) 0.0341(3) -0.0015(2) 0.00516(17) -0.0023(2) C1 0.0209(10) 0.0291(11) 0.0230(10) -0.0003(8) 0.0081(8) -0.0042(9) O1 0.0222(7) 0.0359(8) 0.0435(9) -0.0036(7) 0.0048(6) 0.0028(6) N11 0.0178(8) 0.0234(9) 0.0352(10) -0.0048(7) 0.0081(7) -0.0021(7) N12 0.0180(8) 0.0289(10) 0.0485(11) -0.0065(9) -0.0002(8) -0.0021(8) C11 0.0194(10) 0.0352(12) 0.0323(11) -0.0115(9) 0.0053(8) -0.0048(8) C12 0.0175(10) 0.0384(12) 0.0312(11) -0.0098(9) 0.0054(8) -0.0040(9) C13 0.0236(11) 0.0454(14) 0.0413(13) -0.0080(11) 0.0027(9) -0.0110(10) C14 0.0285(12) 0.0574(16) 0.0432(14) -0.0124(12) -0.0052(10) -0.0139(11) C15 0.0292(12) 0.0611(17) 0.0387(13) -0.0095(12) -0.0077(10) 0.0004(11) C16 0.0276(11) 0.0415(13) 0.0404(13) -0.0064(10) 0.0016(10) -0.0001(10) O12 0.0191(7) 0.0368(9) 0.0406(8) -0.0026(7) -0.0015(6) -0.0075(6) C21 0.0194(10) 0.0395(12) 0.0220(10) -0.0030(9) -0.0007(8) -0.0097(9) C22 0.0191(10) 0.0368(12) 0.0306(11) -0.0014(9) -0.0003(8) -0.0096(9) C23 0.0227(11) 0.0567(16) 0.0422(13) -0.0050(12) 0.0079(9) -0.0081(10) C24 0.0280(12) 0.0641(17) 0.0391(13) 0.0095(12) 0.0076(10) -0.0134(11) C25 0.0306(12) 0.0513(15) 0.0372(13) 0.0113(11) 0.0003(10) -0.0144(11) C26 0.0270(11) 0.0397(13) 0.0319(11) 0.0015(10) -0.0025(9) -0.0060(9) C2 0.0215(10) 0.0351(13) 0.0215(10) -0.0051(9) -0.0016(8) -0.0076(9) O2 0.0401(9) 0.0346(9) 0.0534(10) -0.0133(8) 0.0159(8) -0.0153(7) N21 0.0247(9) 0.0306(10) 0.0307(9) -0.0020(8) 0.0067(7) -0.0066(8) N22 0.0174(8) 0.0294(10) 0.0354(10) -0.0070(8) 0.0040(7) -0.0055(7) C31 0.0225(10) 0.0254(11) 0.0252(10) 0.0021(8) 0.0039(8) -0.0012(8) C32 0.0233(10) 0.0231(10) 0.0226(10) 0.0030(8) 0.0037(8) -0.0051(8) C33 0.0188(9) 0.0339(11) 0.0338(11) 0.0010(9) 0.0053(8) -0.0048(9) C34 0.0298(11) 0.0367(13) 0.0344(12) -0.0010(10) 0.0119(9) 0.0005(9) C35 0.0384(12) 0.0352(12) 0.0307(12) -0.0078(10) 0.0048(9) -0.0009(10) C36 0.0254(10) 0.0378(12) 0.0330(12) -0.0064(10) -0.0005(9) -0.0035(9) O32 0.0178(7) 0.0376(8) 0.0318(8) -0.0095(6) 0.0011(6) -0.0063(6) C41 0.0195(10) 0.0366(12) 0.0227(10) -0.0027(9) 0.0055(8) -0.0042(9) C42 0.0180(9) 0.0407(12) 0.0217(10) -0.0006(9) 0.0028(8) -0.0070(9) C43 0.0317(12) 0.0404(13) 0.0357(12) 0.0090(10) 0.0028(9) -0.0068(10) C44 0.0333(12) 0.0561(16) 0.0338(12) 0.0154(11) -0.0057(10) -0.0028(11) C45 0.0265(11) 0.0577(16) 0.0300(12) 0.0025(11) -0.0063(9) -0.0061(11) C46 0.0257(11) 0.0450(14) 0.0307(11) -0.0052(10) -0.0012(9) -0.0104(10) C3 0.0224(10) 0.0353(12) 0.0233(10) -0.0102(9) 0.0055(8) -0.0052(9) O3 0.0159(7) 0.0427(9) 0.0523(9) -0.0027(8) 0.0082(6) -0.0078(6) N31 0.0155(8) 0.0346(10) 0.0366(10) -0.0053(8) 0.0020(7) -0.0070(8) N32 0.0169(8) 0.0343(10) 0.0366(10) -0.0031(8) 0.0095(7) -0.0059(8) C51 0.0216(10) 0.0364(12) 0.0210(10) -0.0024(9) 0.0008(8) -0.0094(9) C52 0.0182(9) 0.0367(12) 0.0232(10) -0.0014(9) 0.0025(8) -0.0104(8) C53 0.0267(11) 0.0388(13) 0.0363(12) 0.0054(10) -0.0012(9) -0.0056(9) C54 0.0398(13) 0.0513(15) 0.0391(13) 0.0200(11) 0.0007(11) -0.0116(12) C55 0.0322(12) 0.0607(17) 0.0340(12) 0.0155(12) 0.0067(10) -0.0121(11) C56 0.0253(11) 0.0560(15) 0.0298(11) 0.0012(11) 0.0072(9) -0.0076(10) O52 0.0248(7) 0.0272(8) 0.0427(8) -0.0066(7) 0.0160(6) -0.0085(6) C61 0.0234(10) 0.0204(10) 0.0238(10) 0.0012(8) 0.0027(8) -0.0007(8) C62 0.0230(10) 0.0244(10) 0.0247(10) -0.0004(8) 0.0047(8) 0.0013(8) C63 0.0276(11) 0.0280(11) 0.0353(12) -0.0011(9) 0.0014(9) -0.0051(9) C64 0.0412(13) 0.0238(11) 0.0382(12) -0.0060(9) 0.0015(10) -0.0002(10) C65 0.0377(12) 0.0292(12) 0.0390(12) -0.0043(10) 0.0107(10) 0.0066(10) C66 0.0265(10) 0.0276(11) 0.0387(12) -0.0019(9) 0.0093(9) 0.0010(9) N1 0.0293(9) 0.0284(9) 0.0224(8) 0.0042(7) -0.0026(7) -0.0038(7) C71 0.0308(11) 0.0285(11) 0.0246(11) -0.0030(9) -0.0004(8) -0.0068(9) C72 0.0416(13) 0.0329(13) 0.0325(12) 0.0017(9) 0.0009(10) -0.0100(10) C73 0.0551(15) 0.0487(15) 0.0339(13) -0.0013(11) 0.0003(11) -0.0229(12) C74 0.0590(16) 0.0542(16) 0.0381(14) -0.0059(12) 0.0087(12) -0.0286(13) C81 0.0432(12) 0.0331(12) 0.0200(10) 0.0003(9) 0.0019(9) -0.0088(10) C82 0.0398(12) 0.0387(13) 0.0365(12) -0.0010(10) 0.0126(10) -0.0045(10) C83 0.0671(17) 0.0397(14) 0.0383(13) 0.0005(11) 0.0217(12) -0.0003(12) C84 0.0625(16) 0.0361(14) 0.0447(14) 0.0071(12) -0.0039(12) -0.0027(12) C91 0.0319(11) 0.0316(11) 0.0184(10) 0.0047(9) 0.0006(8) -0.0036(9) C92 0.0307(11) 0.0344(12) 0.0304(11) 0.0035(9) 0.0004(9) -0.0051(9) C93 0.0285(11) 0.0284(11) 0.0319(11) 0.0025(9) 0.0059(9) 0.0004(9) C94 0.0339(12) 0.0319(13) 0.0534(15) 0.0034(11) 0.0084(11) -0.0021(10) C101 0.0329(12) 0.0396(13) 0.0418(13) 0.0187(11) -0.0094(10) -0.0060(10) C102 0.0384(14) 0.0356(14) 0.095(2) 0.0023(15) -0.0019(14) 0.0085(11) C103 0.055(4) 0.034(4) 0.058(4) 0.010(3) 0.006(3) 0.014(3) C104 0.042(4) 0.093(4) 0.044(3) -0.003(3) 0.003(2) 0.019(3) C105 0.041(5) 0.046(5) 0.063(5) 0.012(4) 0.015(4) 0.021(4) C106 0.091(6) 0.061(5) 0.077(5) 0.034(4) 0.047(4) 0.052(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 O1 1.224(2) . ? C1 N12 1.372(3) . ? C1 N11 1.381(2) . ? N11 C61 1.413(2) . ? N11 H11 0.90(2) . ? N12 C11 1.421(3) . ? N12 H12 0.85(3) . ? C11 C16 1.392(3) . ? C11 C12 1.399(3) . ? C12 C13 1.387(3) . ? C12 O12 1.408(2) . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(4) . ? C14 H14 0.9500 . ? C15 C16 1.393(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? O12 C22 1.402(3) . ? C21 C22 1.395(3) . ? C21 C26 1.401(3) . ? C21 N21 1.417(2) . ? C22 C23 1.396(3) . ? C23 C24 1.384(3) . ? C23 H23 0.9500 . ? C24 C25 1.388(3) . ? C24 H24 0.9500 . ? C25 C26 1.396(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C2 O2 1.222(2) . ? C2 N22 1.378(3) . ? C2 N21 1.387(3) . ? N21 H21 0.88(2) . ? N22 C31 1.423(2) . ? N22 H22 0.87(3) . ? C31 C36 1.389(3) . ? C31 C32 1.399(3) . ? C32 C33 1.387(3) . ? C32 O32 1.396(2) . ? C33 C34 1.396(3) . ? C33 H33 0.9500 . ? C34 C35 1.385(3) . ? C34 H34 0.9500 . ? C35 C36 1.391(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? O32 C42 1.400(2) . ? C41 C42 1.400(3) . ? C41 C46 1.405(3) . ? C41 N31 1.410(3) . ? C42 C43 1.388(3) . ? C43 C44 1.392(3) . ? C43 H43 0.9500 . ? C44 C45 1.382(3) . ? C44 H44 0.9500 . ? C45 C46 1.382(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C3 O3 1.227(2) . ? C3 N31 1.375(3) . ? C3 N32 1.380(3) . ? N31 H31 0.86(3) . ? N32 C51 1.414(3) . ? N32 H32 0.85(2) . ? C51 C56 1.399(3) . ? C51 C52 1.399(3) . ? C52 C53 1.389(3) . ? C52 O52 1.404(2) . ? C53 C54 1.396(3) . ? C53 H53 0.9500 . ? C54 C55 1.378(3) . ? C54 H54 0.9500 . ? C55 C56 1.388(3) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? O52 C62 1.400(2) . ? C61 C66 1.393(3) . ? C61 C62 1.402(3) . ? C62 C63 1.383(3) . ? C63 C64 1.394(3) . ? C63 H63 0.9500 . ? C64 C65 1.389(3) . ? C64 H64 0.9500 . ? C65 C66 1.392(3) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? N1 C101 1.528(3) . ? N1 C71 1.528(2) . ? N1 C81 1.530(3) . ? N1 C91 1.531(2) . ? C71 C72 1.525(3) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C72 C73 1.516(3) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 C74 1.516(3) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 H74A 0.9800 . ? C74 H74B 0.9800 . ? C74 H74C 0.9800 . ? C81 C82 1.526(3) . ? C81 H81A 0.9900 . ? C81 H81B 0.9900 . ? C82 C83 1.533(3) . ? C82 H82A 0.9900 . ? C82 H82B 0.9900 . ? C83 C84 1.520(3) . ? C83 H83A 0.9900 . ? C83 H83B 0.9900 . ? C84 H84A 0.9800 . ? C84 H84B 0.9800 . ? C84 H84C 0.9800 . ? C91 C92 1.522(3) . ? C91 H91A 0.9900 . ? C91 H91B 0.9900 . ? C92 C93 1.526(3) . ? C92 H92A 0.9900 . ? C92 H92B 0.9900 . ? C93 C94 1.530(3) . ? C93 H93A 0.9900 . ? C93 H93B 0.9900 . ? C94 H94A 0.9800 . ? C94 H94B 0.9800 . ? C94 H94C 0.9800 . ? C101 C102 1.524(4) . ? C101 H10A 0.9900 . ? C101 H10B 0.9900 . ? C102 C103 1.517(6) . ? C102 C105 1.576(7) . ? C102 H10C 0.9900 . ? C102 H10D 0.9900 . ? C102 H10E 0.9900 . ? C102 H10F 0.9900 . ? C103 C104 1.496(7) . ? C103 H10G 0.9900 . ? C103 H10H 0.9900 . ? C104 H10I 0.9800 . ? C104 H10J 0.9800 . ? C104 H10K 0.9800 . ? C105 C106 1.518(7) . ? C105 H10L 0.9900 . ? C105 H10M 0.9900 . ? C106 H10N 0.9800 . ? C106 H10O 0.9800 . ? C106 H10P 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 O1 C1 N12 124.40(18) . . ? O1 C1 N11 124.06(18) . . ? N12 C1 N11 111.53(17) . . ? C1 N11 C61 124.70(17) . . ? C1 N11 H11 117.0(14) . . ? C61 N11 H11 118.3(14) . . ? C1 N12 C11 124.00(18) . . ? C1 N12 H12 119.7(19) . . ? C11 N12 H12 111.8(19) . . ? C16 C11 C12 119.05(19) . . ? C16 C11 N12 122.3(2) . . ? C12 C11 N12 118.58(19) . . ? C13 C12 C11 121.3(2) . . ? C13 C12 O12 124.2(2) . . ? C11 C12 O12 114.57(16) . . ? C12 C13 C14 118.8(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.9(2) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C22 O12 C12 118.01(15) . . ? C22 C21 C26 118.76(18) . . ? C22 C21 N21 116.98(19) . . ? C26 C21 N21 124.20(19) . . ? C21 C22 C23 121.1(2) . . ? C21 C22 O12 117.75(17) . . ? C23 C22 O12 121.0(2) . . ? C24 C23 C22 119.8(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 119.5(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 121.1(2) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 119.6(2) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? O2 C2 N22 124.44(19) . . ? O2 C2 N21 124.15(18) . . ? N22 C2 N21 111.40(18) . . ? C2 N21 C21 126.82(19) . . ? C2 N21 H21 118.6(14) . . ? C21 N21 H21 114.1(14) . . ? C2 N22 C31 122.27(18) . . ? C2 N22 H22 116.5(16) . . ? C31 N22 H22 118.0(16) . . ? C36 C31 C32 119.00(18) . . ? C36 C31 N22 122.01(17) . . ? C32 C31 N22 118.95(17) . . ? C33 C32 O32 124.49(17) . . ? C33 C32 C31 120.82(18) . . ? O32 C32 C31 114.67(16) . . ? C32 C33 C34 119.63(18) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 119.79(19) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 120.4(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 120.29(19) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C32 O32 C42 119.56(15) . . ? C42 C41 C46 117.91(19) . . ? C42 C41 N31 118.48(17) . . ? C46 C41 N31 123.44(19) . . ? C43 C42 C41 121.55(18) . . ? C43 C42 O32 121.92(19) . . ? C41 C42 O32 116.36(17) . . ? C42 C43 C44 119.4(2) . . ? C42 C43 H43 120.3 . . ? C44 C43 H43 120.3 . . ? C45 C44 C43 119.8(2) . . ? C45 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? C44 C45 C46 120.9(2) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C45 C46 C41 120.4(2) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? O3 C3 N31 123.50(19) . . ? O3 C3 N32 124.00(19) . . ? N31 C3 N32 112.50(16) . . ? C3 N31 C41 125.08(16) . . ? C3 N31 H31 119.0(17) . . ? C41 N31 H31 115.9(17) . . ? C3 N32 C51 125.84(17) . . ? C3 N32 H32 118.8(16) . . ? C51 N32 H32 115.1(16) . . ? C56 C51 C52 118.4(2) . . ? C56 C51 N32 123.63(19) . . ? C52 C51 N32 117.90(16) . . ? C53 C52 C51 121.38(18) . . ? C53 C52 O52 123.86(18) . . ? C51 C52 O52 114.60(18) . . ? C52 C53 C54 118.9(2) . . ? C52 C53 H53 120.5 . . ? C54 C53 H53 120.5 . . ? C55 C54 C53 120.4(2) . . ? C55 C54 H54 119.8 . . ? C53 C54 H54 119.8 . . ? C54 C55 C56 120.5(2) . . ? C54 C55 H55 119.7 . . ? C56 C55 H55 119.7 . . ? C55 C56 C51 120.3(2) . . ? C55 C56 H56 119.8 . . ? C51 C56 H56 119.8 . . ? C62 O52 C52 121.22(15) . . ? C66 C61 C62 118.73(18) . . ? C66 C61 N11 122.94(17) . . ? C62 C61 N11 118.22(16) . . ? C63 C62 O52 124.00(17) . . ? C63 C62 C61 121.18(18) . . ? O52 C62 C61 114.64(16) . . ? C62 C63 C64 119.52(19) . . ? C62 C63 H63 120.2 . . ? C64 C63 H63 120.2 . . ? C65 C64 C63 119.98(19) . . ? C65 C64 H64 120.0 . . ? C63 C64 H64 120.0 . . ? C64 C65 C66 120.29(19) . . ? C64 C65 H65 119.9 . . ? C66 C65 H65 119.9 . . ? C65 C66 C61 120.29(19) . . ? C65 C66 H66 119.9 . . ? C61 C66 H66 119.9 . . ? C101 N1 C71 111.01(16) . . ? C101 N1 C81 107.39(16) . . ? C71 N1 C81 110.68(15) . . ? C101 N1 C91 110.53(15) . . ? C71 N1 C91 107.03(14) . . ? C81 N1 C91 110.22(15) . . ? C72 C71 N1 115.60(16) . . ? C72 C71 H71A 108.4 . . ? N1 C71 H71A 108.4 . . ? C72 C71 H71B 108.4 . . ? N1 C71 H71B 108.4 . . ? H71A C71 H71B 107.4 . . ? C73 C72 C71 110.22(18) . . ? C73 C72 H72A 109.6 . . ? C71 C72 H72A 109.6 . . ? C73 C72 H72B 109.6 . . ? C71 C72 H72B 109.6 . . ? H72A C72 H72B 108.1 . . ? C74 C73 C72 113.06(19) . . ? C74 C73 H73A 109.0 . . ? C72 C73 H73A 109.0 . . ? C74 C73 H73B 109.0 . . ? C72 C73 H73B 109.0 . . ? H73A C73 H73B 107.8 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C82 C81 N1 115.26(16) . . ? C82 C81 H81A 108.5 . . ? N1 C81 H81A 108.5 . . ? C82 C81 H81B 108.5 . . ? N1 C81 H81B 108.5 . . ? H81A C81 H81B 107.5 . . ? C81 C82 C83 112.2(2) . . ? C81 C82 H82A 109.2 . . ? C83 C82 H82A 109.2 . . ? C81 C82 H82B 109.2 . . ? C83 C82 H82B 109.2 . . ? H82A C82 H82B 107.9 . . ? C84 C83 C82 113.10(19) . . ? C84 C83 H83A 109.0 . . ? C82 C83 H83A 109.0 . . ? C84 C83 H83B 109.0 . . ? C82 C83 H83B 109.0 . . ? H83A C83 H83B 107.8 . . ? C83 C84 H84A 109.5 . . ? C83 C84 H84B 109.5 . . ? H84A C84 H84B 109.5 . . ? C83 C84 H84C 109.5 . . ? H84A C84 H84C 109.5 . . ? H84B C84 H84C 109.5 . . ? C92 C91 N1 116.20(16) . . ? C92 C91 H91A 108.2 . . ? N1 C91 H91A 108.2 . . ? C92 C91 H91B 108.2 . . ? N1 C91 H91B 108.2 . . ? H91A C91 H91B 107.4 . . ? C91 C92 C93 110.21(16) . . ? C91 C92 H92A 109.6 . . ? C93 C92 H92A 109.6 . . ? C91 C92 H92B 109.6 . . ? C93 C92 H92B 109.6 . . ? H92A C92 H92B 108.1 . . ? C92 C93 C94 111.79(17) . . ? C92 C93 H93A 109.3 . . ? C94 C93 H93A 109.3 . . ? C92 C93 H93B 109.3 . . ? C94 C93 H93B 109.3 . . ? H93A C93 H93B 107.9 . . ? C93 C94 H94A 109.5 . . ? C93 C94 H94B 109.5 . . ? H94A C94 H94B 109.5 . . ? C93 C94 H94C 109.5 . . ? H94A C94 H94C 109.5 . . ? H94B C94 H94C 109.5 . . ? C102 C101 N1 115.42(19) . . ? C102 C101 H10A 108.4 . . ? N1 C101 H10A 108.4 . . ? C102 C101 H10B 108.4 . . ? N1 C101 H10B 108.4 . . ? H10A C101 H10B 107.5 . . ? C103 C102 C101 123.4(3) . . ? C103 C102 C105 28.3(2) . . ? C101 C102 C105 98.4(3) . . ? C103 C102 H10C 106.5 . . ? C101 C102 H10C 106.5 . . ? C105 C102 H10C 131.2 . . ? C103 C102 H10D 106.5 . . ? C101 C102 H10D 106.5 . . ? C105 C102 H10D 105.5 . . ? H10C C102 H10D 106.5 . . ? C103 C102 H10E 108.3 . . ? C101 C102 H10E 112.1 . . ? C105 C102 H10E 112.1 . . ? H10C C102 H10E 96.5 . . ? H10D C102 H10E 10.2 . . ? C103 C102 H10F 88.7 . . ? C101 C102 H10F 112.1 . . ? C105 C102 H10F 112.1 . . ? H10C C102 H10F 19.3 . . ? H10D C102 H10F 119.9 . . ? H10E C102 H10F 109.7 . . ? C104 C103 C102 109.9(5) . . ? C104 C103 H10G 109.7 . . ? C102 C103 H10G 109.7 . . ? C104 C103 H10H 109.7 . . ? C102 C103 H10H 109.7 . . ? H10G C103 H10H 108.2 . . ? C103 C104 H10I 109.5 . . ? C103 C104 H10J 109.5 . . ? H10I C104 H10J 109.5 . . ? C103 C104 H10K 109.5 . . ? H10I C104 H10K 109.5 . . ? H10J C104 H10K 109.5 . . ? C106 C105 C102 107.4(6) . . ? C106 C105 H10L 110.2 . . ? C102 C105 H10L 110.2 . . ? C106 C105 H10M 110.2 . . ? C102 C105 H10M 110.2 . . ? H10L C105 H10M 108.5 . . ? C105 C106 H10N 109.5 . . ? C105 C106 H10O 109.5 . . ? H10N C106 H10O 109.5 . . ? C105 C106 H10P 109.5 . . ? H10N C106 H10P 109.5 . . ? H10O C106 H10P 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 O1 C1 N11 C61 7.4(3) . . . . ? N12 C1 N11 C61 -173.72(17) . . . . ? O1 C1 N12 C11 -7.8(3) . . . . ? N11 C1 N12 C11 173.32(18) . . . . ? C1 N12 C11 C16 52.4(3) . . . . ? C1 N12 C11 C12 -130.4(2) . . . . ? C16 C11 C12 C13 0.7(3) . . . . ? N12 C11 C12 C13 -176.56(19) . . . . ? C16 C11 C12 O12 -179.95(18) . . . . ? N12 C11 C12 O12 2.8(3) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? O12 C12 C13 C14 179.44(19) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C12 C11 C16 C15 0.3(3) . . . . ? N12 C11 C16 C15 177.5(2) . . . . ? C14 C15 C16 C11 -0.8(3) . . . . ? C13 C12 O12 C22 4.2(3) . . . . ? C11 C12 O12 C22 -175.13(17) . . . . ? C26 C21 C22 C23 3.4(3) . . . . ? N21 C21 C22 C23 -173.80(18) . . . . ? C26 C21 C22 O12 179.22(17) . . . . ? N21 C21 C22 O12 2.0(3) . . . . ? C12 O12 C22 C21 109.41(19) . . . . ? C12 O12 C22 C23 -74.8(2) . . . . ? C21 C22 C23 C24 -3.2(3) . . . . ? O12 C22 C23 C24 -178.93(19) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? C23 C24 C25 C26 2.4(3) . . . . ? C24 C25 C26 C21 -2.2(3) . . . . ? C22 C21 C26 C25 -0.7(3) . . . . ? N21 C21 C26 C25 176.29(19) . . . . ? O2 C2 N21 C21 15.5(3) . . . . ? N22 C2 N21 C21 -165.22(17) . . . . ? C22 C21 N21 C2 -171.64(18) . . . . ? C26 C21 N21 C2 11.3(3) . . . . ? O2 C2 N22 C31 -5.7(3) . . . . ? N21 C2 N22 C31 175.04(17) . . . . ? C2 N22 C31 C36 58.3(3) . . . . ? C2 N22 C31 C32 -124.1(2) . . . . ? C36 C31 C32 C33 -1.0(3) . . . . ? N22 C31 C32 C33 -178.73(18) . . . . ? C36 C31 C32 O32 177.78(18) . . . . ? N22 C31 C32 O32 0.0(3) . . . . ? O32 C32 C33 C34 -178.57(19) . . . . ? C31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C35 0.5(3) . . . . ? C33 C34 C35 C36 -0.2(3) . . . . ? C32 C31 C36 C35 1.3(3) . . . . ? N22 C31 C36 C35 178.98(19) . . . . ? C34 C35 C36 C31 -0.7(3) . . . . ? C33 C32 O32 C42 -7.2(3) . . . . ? C31 C32 O32 C42 174.11(17) . . . . ? C46 C41 C42 C43 1.7(3) . . . . ? N31 C41 C42 C43 -173.78(18) . . . . ? C46 C41 C42 O32 177.02(16) . . . . ? N31 C41 C42 O32 1.5(3) . . . . ? C32 O32 C42 C43 -59.5(3) . . . . ? C32 O32 C42 C41 125.17(19) . . . . ? C41 C42 C43 C44 -1.4(3) . . . . ? O32 C42 C43 C44 -176.45(18) . . . . ? C42 C43 C44 C45 0.0(3) . . . . ? C43 C44 C45 C46 1.0(3) . . . . ? C44 C45 C46 C41 -0.6(3) . . . . ? C42 C41 C46 C45 -0.7(3) . . . . ? N31 C41 C46 C45 174.56(19) . . . . ? O3 C3 N31 C41 11.3(3) . . . . ? N32 C3 N31 C41 -168.67(17) . . . . ? C42 C41 N31 C3 -155.02(19) . . . . ? C46 C41 N31 C3 29.8(3) . . . . ? O3 C3 N32 C51 3.1(3) . . . . ? N31 C3 N32 C51 -176.95(17) . . . . ? C3 N32 C51 C56 28.4(3) . . . . ? C3 N32 C51 C52 -154.09(18) . . . . ? C56 C51 C52 C53 1.1(3) . . . . ? N32 C51 C52 C53 -176.53(18) . . . . ? C56 C51 C52 O52 176.68(17) . . . . ? N32 C51 C52 O52 -1.0(2) . . . . ? C51 C52 C53 C54 -2.4(3) . . . . ? O52 C52 C53 C54 -177.52(19) . . . . ? C52 C53 C54 C55 1.7(3) . . . . ? C53 C54 C55 C56 0.3(3) . . . . ? C54 C55 C56 C51 -1.6(3) . . . . ? C52 C51 C56 C55 0.9(3) . . . . ? N32 C51 C56 C55 178.39(19) . . . . ? C53 C52 O52 C62 -28.6(3) . . . . ? C51 C52 O52 C62 155.97(17) . . . . ? C1 N11 C61 C66 35.1(3) . . . . ? C1 N11 C61 C62 -148.62(19) . . . . ? C52 O52 C62 C63 -33.8(3) . . . . ? C52 O52 C62 C61 151.11(17) . . . . ? C66 C61 C62 C63 1.6(3) . . . . ? N11 C61 C62 C63 -174.81(18) . . . . ? C66 C61 C62 O52 176.83(17) . . . . ? N11 C61 C62 O52 0.4(2) . . . . ? O52 C62 C63 C64 -176.42(19) . . . . ? C61 C62 C63 C64 -1.6(3) . . . . ? C62 C63 C64 C65 0.6(3) . . . . ? C63 C64 C65 C66 0.4(3) . . . . ? C64 C65 C66 C61 -0.4(3) . . . . ? C62 C61 C66 C65 -0.6(3) . . . . ? N11 C61 C66 C65 175.66(19) . . . . ? C101 N1 C71 C72 58.1(2) . . . . ? C81 N1 C71 C72 -61.1(2) . . . . ? C91 N1 C71 C72 178.81(17) . . . . ? N1 C71 C72 C73 171.31(19) . . . . ? C71 C72 C73 C74 178.1(2) . . . . ? C101 N1 C81 C82 -170.82(17) . . . . ? C71 N1 C81 C82 -49.5(2) . . . . ? C91 N1 C81 C82 68.7(2) . . . . ? N1 C81 C82 C83 -151.75(18) . . . . ? C81 C82 C83 C84 76.6(3) . . . . ? C101 N1 C91 C92 -53.7(2) . . . . ? C71 N1 C91 C92 -174.67(17) . . . . ? C81 N1 C91 C92 64.9(2) . . . . ? N1 C91 C92 C93 -169.34(17) . . . . ? C91 C92 C93 C94 176.77(17) . . . . ? C71 N1 C101 C102 59.9(2) . . . . ? C81 N1 C101 C102 -179.01(19) . . . . ? C91 N1 C101 C102 -58.7(2) . . . . ? N1 C101 C102 C103 -170.9(3) . . . . ? N1 C101 C102 C105 174.8(4) . . . . ? C101 C102 C103 C104 -58.9(6) . . . . ? C105 C102 C103 C104 -27.8(8) . . . . ? C103 C102 C105 C106 18.7(7) . . . . ? C101 C102 C105 C106 172.9(5) . . . . ? 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 N11 H11 Cl1 0.90(2) 2.50(2) 3.3516(18) 159.4(19) . N12 H12 Cl1 0.85(3) 2.58(3) 3.3302(19) 149(2) . N21 H21 Cl1 0.88(2) 2.75(2) 3.5341(19) 149.1(18) . N22 H22 Cl1 0.87(3) 2.47(3) 3.3223(19) 168(2) . N31 H31 Cl1 0.86(3) 2.51(3) 3.3327(17) 160(2) . N32 H32 Cl1 0.85(2) 2.65(2) 3.4272(18) 153(2) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.208 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.044 data_boeh65 _database_code_depnum_ccdc_archive 'CCDC 667519' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H66 N6 O9 S2' _chemical_formula_weight 1019.26 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 Orthorhombic _symmetry_space_group_name_H-M 'P 212121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.8190(8) _cell_length_b 17.9176(10) _cell_length_c 21.6376(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5357.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18419 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_T_max 0.9490 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19313 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.05 _reflns_number_total 9414 _reflns_number_gt 8547 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0618P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0079(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 9414 _refine_ls_number_parameters 678 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0859 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.74322(11) 0.15853(7) 0.61167(8) 0.0371(4) Uani 1 1 d . . . O2 O 0.67230(11) 0.57959(8) 0.47155(7) 0.0395(4) Uani 1 1 d . . . O3 O 0.46454(10) 0.22141(7) 0.70512(7) 0.0312(3) Uani 1 1 d . . . O4 O 0.39412(10) 0.50733(7) 0.58340(6) 0.0290(3) Uani 1 1 d . . . O5 O 0.30865(14) 0.43333(8) 0.79213(7) 0.0456(4) Uani 1 1 d . . . O6 O 0.84225(9) 0.40912(7) 0.60298(6) 0.0257(3) Uani 1 1 d . . . N11 N 0.75084(12) 0.28412(8) 0.63237(8) 0.0265(3) Uani 1 1 d . . . H11 H 0.715(2) 0.3270(15) 0.6329(12) 0.049(7) Uiso 1 1 d . . . N12 N 0.60364(12) 0.22626(9) 0.62100(8) 0.0287(4) Uani 1 1 d . . . H12 H 0.5754(17) 0.2683(14) 0.6338(11) 0.037(6) Uiso 1 1 d . . . N21 N 0.72602(11) 0.50199(9) 0.54850(8) 0.0264(4) Uani 1 1 d . . . H21 H 0.7063(17) 0.4673(14) 0.5723(12) 0.038(7) Uiso 1 1 d . . . N22 N 0.56528(11) 0.50384(9) 0.52302(8) 0.0250(3) Uani 1 1 d . . . H22 H 0.5589(16) 0.4807(12) 0.5603(11) 0.029(6) Uiso 1 1 d . . . N51 N 0.34782(13) 0.33376(9) 0.73031(8) 0.0283(4) Uani 1 1 d . . . H51 H 0.3706(18) 0.3256(13) 0.6950(12) 0.038(7) Uiso 1 1 d . . . N52 N 0.35407(12) 0.45202(9) 0.69126(7) 0.0257(3) Uani 1 1 d . . . H52 H 0.3724(16) 0.4286(12) 0.6576(11) 0.032(6) Uiso 1 1 d . . . C1 C 0.70242(14) 0.21794(10) 0.62119(9) 0.0241(4) Uani 1 1 d . . . C2 C 0.65637(13) 0.53212(10) 0.51121(9) 0.0236(4) Uani 1 1 d . . . C5 C 0.33417(14) 0.40909(10) 0.74262(9) 0.0257(4) Uani 1 1 d . . . C11 C 0.85061(13) 0.28856(10) 0.64511(8) 0.0224(4) Uani 1 1 d . . . C12 C 0.90217(14) 0.23117(10) 0.67293(9) 0.0256(4) Uani 1 1 d . . . H12A H 0.8697 0.1862 0.6834 0.031 Uiso 1 1 calc R . . C13 C 1.00043(14) 0.23811(10) 0.68580(9) 0.0258(4) Uani 1 1 d . . . C14 C 1.04634(14) 0.30512(10) 0.67128(10) 0.0267(4) Uani 1 1 d . . . H14 H 1.1131 0.3107 0.6806 0.032 Uiso 1 1 calc R . . C15 C 0.99676(13) 0.36466(9) 0.64333(9) 0.0227(4) Uani 1 1 d . . . C16 C 0.89975(13) 0.35514(9) 0.63062(8) 0.0212(4) Uani 1 1 d . . . C17 C 1.05402(15) 0.17324(10) 0.71742(10) 0.0321(5) Uani 1 1 d . . . C18 C 1.04927(13) 0.43854(10) 0.63053(9) 0.0246(4) Uani 1 1 d . . . C21 C 0.82386(13) 0.52437(10) 0.55321(9) 0.0231(4) Uani 1 1 d . . . C22 C 0.86058(14) 0.59134(10) 0.53123(9) 0.0264(4) Uani 1 1 d . . . H22A H 0.8191 0.6251 0.5101 0.032 Uiso 1 1 calc R . . C23 C 0.95834(14) 0.60982(10) 0.53991(9) 0.0254(4) Uani 1 1 d . . . C24 C 1.01738(14) 0.56019(10) 0.57196(9) 0.0248(4) Uani 1 1 d . . . H24 H 1.0832 0.5730 0.5788 0.030 Uiso 1 1 calc R . . C25 C 0.98253(14) 0.49134(10) 0.59461(9) 0.0233(4) Uani 1 1 d . . . C26 C 0.88662(13) 0.47487(9) 0.58419(9) 0.0224(4) Uani 1 1 d . . . C27 C 0.99539(15) 0.68411(10) 0.51247(10) 0.0304(4) Uani 1 1 d . . . C31 C 0.53947(14) 0.16435(11) 0.62043(9) 0.0270(4) Uani 1 1 d . . . C32 C 0.46532(14) 0.16221(10) 0.66350(9) 0.0257(4) Uani 1 1 d . . . C33 C 0.39674(16) 0.10586(11) 0.66231(10) 0.0343(5) Uani 1 1 d . . . H33 H 0.3452 0.1057 0.6914 0.041 Uiso 1 1 calc R . . C34 C 0.40368(17) 0.04946(12) 0.61835(11) 0.0400(5) Uani 1 1 d . . . H34 H 0.3563 0.0111 0.6169 0.048 Uiso 1 1 calc R . . C35 C 0.47915(19) 0.04934(13) 0.57697(11) 0.0444(6) Uani 1 1 d . . . H35 H 0.4851 0.0099 0.5479 0.053 Uiso 1 1 calc R . . C36 C 0.54710(17) 0.10695(13) 0.57745(11) 0.0406(5) Uani 1 1 d . . . H36 H 0.5986 0.1070 0.5484 0.049 Uiso 1 1 calc R . . C41 C 0.48112(13) 0.52288(9) 0.48936(8) 0.0223(4) Uani 1 1 d . . . C42 C 0.39285(14) 0.52551(10) 0.52040(8) 0.0246(4) Uani 1 1 d . . . C43 C 0.30731(15) 0.53889(11) 0.48943(10) 0.0329(5) Uani 1 1 d . . . H43 H 0.2479 0.5397 0.5115 0.039 Uiso 1 1 calc R . . C44 C 0.30774(15) 0.55111(12) 0.42628(10) 0.0352(5) Uani 1 1 d . . . H44 H 0.2491 0.5608 0.4048 0.042 Uiso 1 1 calc R . . C45 C 0.39482(16) 0.54907(11) 0.39483(9) 0.0325(4) Uani 1 1 d . . . H45 H 0.3956 0.5575 0.3515 0.039 Uiso 1 1 calc R . . C46 C 0.48090(15) 0.53500(11) 0.42555(9) 0.0284(4) Uani 1 1 d . . . H46 H 0.5400 0.5336 0.4032 0.034 Uiso 1 1 calc R . . C51 C 0.41364(13) 0.21579(10) 0.76031(9) 0.0252(4) Uani 1 1 d . . . C52 C 0.35552(14) 0.27699(10) 0.77525(9) 0.0246(4) Uani 1 1 d . . . C53 C 0.30655(16) 0.27646(11) 0.83146(10) 0.0324(4) Uani 1 1 d . . . H53 H 0.2666 0.3174 0.8427 0.039 Uiso 1 1 calc R . . C54 C 0.31632(17) 0.21583(12) 0.87116(10) 0.0357(5) Uani 1 1 d . . . H54 H 0.2814 0.2151 0.9090 0.043 Uiso 1 1 calc R . . C55 C 0.37623(16) 0.15656(11) 0.85623(10) 0.0342(5) Uani 1 1 d . . . H55 H 0.3831 0.1159 0.8840 0.041 Uiso 1 1 calc R . . C56 C 0.42609(15) 0.15669(10) 0.80074(10) 0.0319(4) Uani 1 1 d . . . H56 H 0.4683 0.1167 0.7905 0.038 Uiso 1 1 calc R . . C61 C 0.36108(13) 0.55930(10) 0.62635(8) 0.0243(4) Uani 1 1 d . . . C62 C 0.34210(13) 0.52967(10) 0.68506(9) 0.0242(4) Uani 1 1 d . . . C63 C 0.31388(16) 0.57827(11) 0.73225(10) 0.0319(4) Uani 1 1 d . . . H63 H 0.3019 0.5599 0.7727 0.038 Uiso 1 1 calc R . . C64 C 0.30351(17) 0.65431(11) 0.71920(11) 0.0377(5) Uani 1 1 d . . . H64 H 0.2840 0.6874 0.7512 0.045 Uiso 1 1 calc R . . C65 C 0.32091(17) 0.68235(11) 0.66093(11) 0.0363(5) Uani 1 1 d . . . H65 H 0.3127 0.7341 0.6530 0.044 Uiso 1 1 calc R . . C66 C 0.35046(16) 0.63480(11) 0.61389(10) 0.0316(4) Uani 1 1 d . . . H66 H 0.3632 0.6537 0.5737 0.038 Uiso 1 1 calc R . . C171 C 1.16254(19) 0.18592(17) 0.71905(19) 0.0791(12) Uani 1 1 d . . . H17A H 1.1940 0.1435 0.7394 0.119 Uiso 1 1 calc R . . H17B H 1.1766 0.2317 0.7421 0.119 Uiso 1 1 calc R . . H17C H 1.1871 0.1907 0.6767 0.119 Uiso 1 1 calc R . . C172 C 1.0179(2) 0.16655(14) 0.78354(11) 0.0585(7) Uani 1 1 d . . . H17D H 0.9478 0.1583 0.7834 0.088 Uiso 1 1 calc R . . H17E H 1.0326 0.2126 0.8060 0.088 Uiso 1 1 calc R . . H17F H 1.0501 0.1244 0.8038 0.088 Uiso 1 1 calc R . . C173 C 1.0342(2) 0.10070(13) 0.68279(13) 0.0552(7) Uani 1 1 d . . . H17G H 0.9643 0.0916 0.6815 0.083 Uiso 1 1 calc R . . H17H H 1.0663 0.0593 0.7041 0.083 Uiso 1 1 calc R . . H17I H 1.0591 0.1047 0.6405 0.083 Uiso 1 1 calc R . . C181 C 1.07633(17) 0.47429(11) 0.69300(11) 0.0359(5) Uani 1 1 d . . . H18A H 1.1101 0.5216 0.6857 0.054 Uiso 1 1 calc R . . H18B H 1.1187 0.4404 0.7160 0.054 Uiso 1 1 calc R . . H18C H 1.0174 0.4837 0.7170 0.054 Uiso 1 1 calc R . . C182 C 1.14214(15) 0.42320(11) 0.59379(11) 0.0350(5) Uani 1 1 d . . . H18D H 1.1759 0.4704 0.5859 0.052 Uiso 1 1 calc R . . H18E H 1.1256 0.3995 0.5544 0.052 Uiso 1 1 calc R . . H18F H 1.1843 0.3899 0.6176 0.052 Uiso 1 1 calc R . . C271 C 0.93438(18) 0.74955(11) 0.53802(12) 0.0401(5) Uani 1 1 d . . . H27A H 0.9579 0.7966 0.5205 0.060 Uiso 1 1 calc R . . H27B H 0.9401 0.7511 0.5831 0.060 Uiso 1 1 calc R . . H27C H 0.8664 0.7424 0.5266 0.060 Uiso 1 1 calc R . . C272 C 0.98359(19) 0.68113(13) 0.44185(10) 0.0416(5) Uani 1 1 d . . . H27D H 1.0068 0.7280 0.4237 0.062 Uiso 1 1 calc R . . H27E H 0.9151 0.6741 0.4315 0.062 Uiso 1 1 calc R . . H27F H 1.0214 0.6394 0.4253 0.062 Uiso 1 1 calc R . . C273 C 1.10170(16) 0.69884(12) 0.52855(13) 0.0428(6) Uani 1 1 d . . . H27G H 1.1221 0.7463 0.5103 0.064 Uiso 1 1 calc R . . H27H H 1.1419 0.6584 0.5121 0.064 Uiso 1 1 calc R . . H27I H 1.1091 0.7012 0.5736 0.064 Uiso 1 1 calc R . . S1 S 0.60984(4) 0.44945(3) 0.70430(2) 0.03149(12) Uani 1 1 d . . . O1S O 0.61803(10) 0.41268(7) 0.64125(6) 0.0315(3) Uani 1 1 d . . . C1S C 0.6005(2) 0.37431(14) 0.75846(11) 0.0483(6) Uani 1 1 d . . . H1S1 H 0.5370 0.3505 0.7544 0.072 Uiso 1 1 calc R . . H1S2 H 0.6081 0.3937 0.8005 0.072 Uiso 1 1 calc R . . H1S3 H 0.6514 0.3375 0.7501 0.072 Uiso 1 1 calc R . . C2S C 0.72962(17) 0.47960(12) 0.72328(11) 0.0391(5) Uani 1 1 d . . . H2S1 H 0.7474 0.5221 0.6971 0.059 Uiso 1 1 calc R . . H2S2 H 0.7752 0.4386 0.7163 0.059 Uiso 1 1 calc R . . H2S3 H 0.7319 0.4947 0.7668 0.059 Uiso 1 1 calc R . . S2 S 0.36325(5) 0.32650(3) 0.53814(3) 0.04306(15) Uani 1 1 d . . . O2S O 0.40475(14) 0.33112(9) 0.60250(7) 0.0471(4) Uani 1 1 d . . . C3S C 0.3102(2) 0.23583(16) 0.53237(12) 0.0569(7) Uani 1 1 d . . . H3S1 H 0.2512 0.2340 0.5575 0.085 Uiso 1 1 calc R . . H3S2 H 0.3562 0.1984 0.5474 0.085 Uiso 1 1 calc R . . H3S3 H 0.2941 0.2254 0.4891 0.085 Uiso 1 1 calc R . . C4S C 0.4639(2) 0.31052(17) 0.48855(12) 0.0591(7) Uani 1 1 d . . . H4S1 H 0.5031 0.3560 0.4859 0.089 Uiso 1 1 calc R . . H4S2 H 0.4406 0.2970 0.4473 0.089 Uiso 1 1 calc R . . H4S3 H 0.5034 0.2698 0.5052 0.089 Uiso 1 1 calc R . . O1M O 0.7085(2) 0.61204(17) 0.34856(12) 0.0883(9) Uani 1 1 d . . . H1M H 0.702(3) 0.601(2) 0.3831(19) 0.089(13) Uiso 1 1 d . . . C1M C 0.6323(2) 0.65392(17) 0.32454(13) 0.0619(7) Uani 1 1 d . . . H1MA H 0.6479 0.6694 0.2823 0.093 Uiso 1 1 d R . . H1MB H 0.5732 0.6237 0.3242 0.093 Uiso 1 1 d R . . H1MC H 0.6222 0.6982 0.3503 0.093 Uiso 1 1 d 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 O1 0.0323(8) 0.0229(7) 0.0560(10) -0.0080(7) -0.0022(7) 0.0009(6) O2 0.0348(8) 0.0471(9) 0.0365(9) 0.0196(7) -0.0037(7) -0.0078(6) O3 0.0386(8) 0.0213(6) 0.0338(8) -0.0026(6) 0.0151(7) -0.0039(6) O4 0.0358(7) 0.0318(7) 0.0196(7) 0.0073(5) 0.0055(6) 0.0093(6) O5 0.0815(12) 0.0293(7) 0.0258(8) 0.0019(6) 0.0204(8) 0.0073(7) O6 0.0222(7) 0.0180(6) 0.0370(8) 0.0072(5) -0.0013(6) -0.0005(5) N11 0.0252(8) 0.0173(7) 0.0370(10) 0.0017(7) 0.0013(7) -0.0006(6) N12 0.0259(8) 0.0248(8) 0.0353(10) -0.0094(7) 0.0062(7) -0.0055(7) N21 0.0242(8) 0.0217(7) 0.0332(10) 0.0083(7) 0.0000(7) -0.0011(6) N22 0.0255(8) 0.0279(8) 0.0214(9) 0.0055(7) -0.0012(6) 0.0003(6) N51 0.0411(10) 0.0249(8) 0.0190(9) 0.0026(7) 0.0049(7) 0.0024(7) N52 0.0345(9) 0.0244(7) 0.0182(8) 0.0008(6) 0.0023(7) 0.0015(7) C1 0.0266(10) 0.0252(9) 0.0204(10) -0.0008(7) 0.0027(7) -0.0043(8) C2 0.0237(9) 0.0238(9) 0.0234(10) -0.0005(7) 0.0005(8) 0.0006(7) C5 0.0315(10) 0.0247(9) 0.0209(10) 0.0029(7) 0.0033(8) 0.0018(7) C11 0.0233(9) 0.0218(8) 0.0220(10) -0.0016(7) 0.0021(7) -0.0016(7) C12 0.0310(10) 0.0209(8) 0.0249(10) 0.0028(7) 0.0013(8) -0.0031(8) C13 0.0296(10) 0.0218(9) 0.0259(10) 0.0029(7) -0.0021(8) 0.0008(7) C14 0.0234(9) 0.0241(9) 0.0326(11) 0.0016(8) -0.0041(8) -0.0007(7) C15 0.0240(9) 0.0203(8) 0.0240(10) 0.0000(7) 0.0013(8) -0.0006(7) C16 0.0245(9) 0.0181(8) 0.0209(9) 0.0015(7) -0.0008(8) 0.0017(7) C17 0.0358(11) 0.0224(9) 0.0381(12) 0.0083(8) -0.0075(9) 0.0001(8) C18 0.0238(9) 0.0197(8) 0.0304(10) 0.0022(7) -0.0015(8) -0.0018(7) C21 0.0224(9) 0.0214(8) 0.0256(10) -0.0005(7) 0.0024(7) 0.0002(7) C22 0.0300(10) 0.0203(8) 0.0288(10) 0.0023(7) 0.0022(8) 0.0016(7) C23 0.0303(10) 0.0189(8) 0.0268(10) -0.0013(7) 0.0039(8) -0.0013(7) C24 0.0255(9) 0.0206(8) 0.0282(10) 0.0003(7) 0.0017(8) -0.0037(7) C25 0.0258(9) 0.0194(8) 0.0249(10) 0.0005(7) 0.0007(8) 0.0007(7) C26 0.0240(9) 0.0157(8) 0.0273(10) 0.0021(7) 0.0033(8) -0.0014(7) C27 0.0319(10) 0.0223(9) 0.0371(12) 0.0056(8) 0.0031(9) -0.0033(8) C31 0.0271(10) 0.0280(9) 0.0259(10) -0.0029(8) 0.0014(8) -0.0062(8) C32 0.0295(10) 0.0208(8) 0.0268(10) -0.0002(7) -0.0017(8) -0.0002(8) C33 0.0304(10) 0.0317(10) 0.0409(12) 0.0027(9) 0.0045(9) -0.0067(9) C34 0.0439(13) 0.0347(10) 0.0413(13) -0.0009(9) -0.0015(10) -0.0184(10) C35 0.0551(14) 0.0391(12) 0.0389(13) -0.0159(10) 0.0007(11) -0.0146(11) C36 0.0451(13) 0.0423(12) 0.0346(12) -0.0138(10) 0.0099(10) -0.0141(10) C41 0.0253(9) 0.0196(8) 0.0220(10) -0.0004(7) -0.0019(7) -0.0006(7) C42 0.0304(9) 0.0234(8) 0.0199(9) 0.0040(7) 0.0021(8) 0.0023(7) C43 0.0268(10) 0.0372(11) 0.0348(12) 0.0106(9) 0.0018(8) 0.0039(8) C44 0.0332(11) 0.0391(11) 0.0332(12) 0.0086(9) -0.0089(9) 0.0039(9) C45 0.0439(12) 0.0335(10) 0.0201(10) 0.0032(8) -0.0037(9) 0.0017(9) C46 0.0326(10) 0.0317(10) 0.0210(10) 0.0002(8) 0.0035(8) 0.0016(8) C51 0.0245(9) 0.0262(9) 0.0251(10) 0.0005(7) 0.0027(8) -0.0054(7) C52 0.0283(9) 0.0241(9) 0.0213(9) 0.0026(7) -0.0010(8) -0.0019(7) C53 0.0384(11) 0.0331(10) 0.0257(11) 0.0017(8) 0.0048(9) -0.0001(9) C54 0.0478(12) 0.0373(11) 0.0221(11) 0.0040(8) 0.0047(9) -0.0082(10) C55 0.0443(12) 0.0283(9) 0.0299(11) 0.0103(8) -0.0043(9) -0.0058(9) C56 0.0333(10) 0.0228(9) 0.0396(12) 0.0042(8) -0.0025(9) -0.0010(8) C61 0.0235(9) 0.0262(9) 0.0231(10) 0.0012(7) 0.0006(7) 0.0004(7) C62 0.0246(9) 0.0247(9) 0.0233(10) 0.0017(7) -0.0008(7) -0.0036(7) C63 0.0424(12) 0.0284(10) 0.0248(11) 0.0003(8) 0.0037(9) -0.0032(8) C64 0.0527(14) 0.0264(10) 0.0340(12) -0.0049(8) 0.0045(10) -0.0007(9) C65 0.0482(12) 0.0226(9) 0.0382(13) 0.0011(8) 0.0022(10) 0.0010(9) C66 0.0364(11) 0.0290(10) 0.0295(11) 0.0073(8) 0.0026(9) 0.0005(8) C171 0.0377(14) 0.0603(17) 0.139(3) 0.061(2) -0.0170(17) 0.0018(12) C172 0.098(2) 0.0411(13) 0.0365(14) 0.0108(11) -0.0064(14) 0.0142(14) C173 0.085(2) 0.0286(11) 0.0524(16) -0.0013(10) -0.0228(14) 0.0175(12) C181 0.0429(12) 0.0252(9) 0.0396(13) -0.0007(9) -0.0118(10) -0.0034(8) C182 0.0268(10) 0.0321(10) 0.0460(13) 0.0128(9) 0.0059(9) 0.0021(8) C271 0.0505(13) 0.0192(9) 0.0506(14) 0.0043(9) 0.0033(11) 0.0001(9) C272 0.0505(13) 0.0376(11) 0.0367(13) 0.0107(9) 0.0047(11) -0.0062(10) C273 0.0377(12) 0.0286(10) 0.0620(16) 0.0141(10) -0.0033(11) -0.0117(9) S1 0.0315(3) 0.0278(2) 0.0352(3) -0.0027(2) 0.0026(2) 0.0017(2) O1S 0.0308(7) 0.0332(7) 0.0307(8) -0.0002(6) -0.0012(6) 0.0006(6) C1S 0.0595(15) 0.0509(13) 0.0345(13) 0.0045(10) -0.0009(12) -0.0211(12) C2S 0.0407(12) 0.0339(10) 0.0426(13) -0.0061(9) 0.0004(10) -0.0101(9) S2 0.0626(4) 0.0399(3) 0.0267(3) 0.0008(2) -0.0013(3) 0.0060(3) O2S 0.0770(12) 0.0420(8) 0.0223(8) -0.0047(6) -0.0005(8) 0.0028(8) C3S 0.0714(18) 0.0632(16) 0.0361(14) 0.0048(12) -0.0085(13) -0.0208(14) C4S 0.080(2) 0.0637(16) 0.0332(14) -0.0113(12) 0.0128(14) -0.0215(15) O1M 0.0934(18) 0.127(2) 0.0449(14) 0.0242(14) 0.0266(12) 0.0414(16) C1M 0.076(2) 0.0632(16) 0.0467(16) 0.0083(13) 0.0115(14) -0.0002(15) _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 O1 C1 1.222(2) . ? O2 C2 1.228(2) . ? O3 C51 1.390(2) . ? O3 C32 1.392(2) . ? O4 C61 1.393(2) . ? O4 C42 1.402(2) . ? O5 C5 1.209(2) . ? O6 C16 1.387(2) . ? O6 C26 1.389(2) . ? N11 C1 1.383(2) . ? N11 C11 1.408(2) . ? N11 H11 0.92(3) . ? N12 C1 1.373(3) . ? N12 C31 1.420(2) . ? N12 H12 0.89(3) . ? N21 C2 1.367(2) . ? N21 C21 1.414(2) . ? N21 H21 0.85(3) . ? N22 C2 1.381(2) . ? N22 C41 1.414(2) . ? N22 H22 0.91(2) . ? N51 C5 1.389(2) . ? N51 C52 1.411(2) . ? N51 H51 0.84(3) . ? N52 C5 1.379(2) . ? N52 C62 1.407(2) . ? N52 H52 0.88(2) . ? C11 C12 1.388(3) . ? C11 C16 1.408(2) . ? C12 C13 1.392(3) . ? C12 H12A 0.9500 . ? C13 C14 1.394(3) . ? C13 C17 1.539(3) . ? C14 C15 1.405(3) . ? C14 H14 0.9500 . ? C15 C16 1.379(3) . ? C15 C18 1.535(2) . ? C17 C171 1.517(3) . ? C17 C172 1.520(3) . ? C17 C173 1.525(3) . ? C18 C25 1.533(3) . ? C18 C182 1.534(3) . ? C18 C181 1.542(3) . ? C21 C22 1.387(3) . ? C21 C26 1.410(3) . ? C22 C23 1.404(3) . ? C22 H22A 0.9500 . ? C23 C24 1.392(3) . ? C23 C27 1.545(2) . ? C24 C25 1.412(3) . ? C24 H24 0.9500 . ? C25 C26 1.376(3) . ? C27 C273 1.533(3) . ? C27 C272 1.537(3) . ? C27 C271 1.546(3) . ? C31 C32 1.386(3) . ? C31 C36 1.391(3) . ? C32 C33 1.385(3) . ? C33 C34 1.391(3) . ? C33 H33 0.9500 . ? C34 C35 1.375(3) . ? C34 H34 0.9500 . ? C35 C36 1.396(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.393(3) . ? C41 C46 1.398(3) . ? C42 C43 1.380(3) . ? C43 C44 1.384(3) . ? C43 H43 0.9500 . ? C44 C45 1.383(3) . ? C44 H44 0.9500 . ? C45 C46 1.386(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C51 C56 1.384(3) . ? C51 C52 1.397(3) . ? C52 C53 1.392(3) . ? C53 C54 1.391(3) . ? C53 H53 0.9500 . ? C54 C55 1.385(3) . ? C54 H54 0.9500 . ? C55 C56 1.384(3) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C61 C66 1.387(3) . ? C61 C62 1.402(3) . ? C62 C63 1.397(3) . ? C63 C64 1.399(3) . ? C63 H63 0.9500 . ? C64 C65 1.378(3) . ? C64 H64 0.9500 . ? C65 C66 1.389(3) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C171 H17A 0.9800 . ? C171 H17B 0.9800 . ? C171 H17C 0.9800 . ? C172 H17D 0.9800 . ? C172 H17E 0.9800 . ? C172 H17F 0.9800 . ? C173 H17G 0.9800 . ? C173 H17H 0.9800 . ? C173 H17I 0.9800 . ? C181 H18A 0.9800 . ? C181 H18B 0.9800 . ? C181 H18C 0.9800 . ? C182 H18D 0.9800 . ? C182 H18E 0.9800 . ? C182 H18F 0.9800 . ? C271 H27A 0.9800 . ? C271 H27B 0.9800 . ? C271 H27C 0.9800 . ? C272 H27D 0.9800 . ? C272 H27E 0.9800 . ? C272 H27F 0.9800 . ? C273 H27G 0.9800 . ? C273 H27H 0.9800 . ? C273 H27I 0.9800 . ? S1 O1S 1.5192(15) . ? S1 C2S 1.789(2) . ? S1 C1S 1.790(2) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? S2 O2S 1.5083(17) . ? S2 C4S 1.780(3) . ? S2 C3S 1.787(3) . ? C3S H3S1 0.9800 . ? C3S H3S2 0.9800 . ? C3S H3S3 0.9800 . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? O1M C1M 1.393(4) . ? O1M H1M 0.78(4) . ? C1M H1MA 0.9802 . ? C1M H1MB 0.9803 . ? C1M H1MC 0.9802 . ? 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 C51 O3 C32 120.32(14) . . ? C61 O4 C42 119.31(14) . . ? C16 O6 C26 117.69(14) . . ? C1 N11 C11 123.80(16) . . ? C1 N11 H11 117.4(17) . . ? C11 N11 H11 118.8(17) . . ? C1 N12 C31 122.40(16) . . ? C1 N12 H12 121.7(15) . . ? C31 N12 H12 112.9(15) . . ? C2 N21 C21 127.14(16) . . ? C2 N21 H21 114.8(16) . . ? C21 N21 H21 118.0(16) . . ? C2 N22 C41 124.47(16) . . ? C2 N22 H22 114.8(14) . . ? C41 N22 H22 119.1(14) . . ? C5 N51 C52 125.35(17) . . ? C5 N51 H51 113.2(16) . . ? C52 N51 H51 118.3(16) . . ? C5 N52 C62 127.20(16) . . ? C5 N52 H52 117.4(14) . . ? C62 N52 H52 115.3(14) . . ? O1 C1 N12 123.55(17) . . ? O1 C1 N11 123.59(17) . . ? N12 C1 N11 112.85(16) . . ? O2 C2 N21 124.04(17) . . ? O2 C2 N22 123.15(17) . . ? N21 C2 N22 112.81(16) . . ? O5 C5 N52 124.89(17) . . ? O5 C5 N51 123.99(17) . . ? N52 C5 N51 111.12(16) . . ? C12 C11 C16 118.46(16) . . ? C12 C11 N11 123.06(16) . . ? C16 C11 N11 118.45(16) . . ? C11 C12 C13 121.42(17) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C12 C13 C14 118.43(17) . . ? C12 C13 C17 119.40(17) . . ? C14 C13 C17 122.13(17) . . ? C13 C14 C15 121.95(17) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C16 C15 C14 117.78(16) . . ? C16 C15 C18 122.03(16) . . ? C14 C15 C18 120.14(16) . . ? C15 C16 O6 123.81(15) . . ? C15 C16 C11 121.96(16) . . ? O6 C16 C11 114.23(16) . . ? C171 C17 C172 108.3(2) . . ? C171 C17 C173 108.5(2) . . ? C172 C17 C173 109.6(2) . . ? C171 C17 C13 111.89(17) . . ? C172 C17 C13 108.67(18) . . ? C173 C17 C13 109.80(17) . . ? C25 C18 C182 110.55(16) . . ? C25 C18 C15 109.84(15) . . ? C182 C18 C15 109.54(15) . . ? C25 C18 C181 109.52(15) . . ? C182 C18 C181 109.01(17) . . ? C15 C18 C181 108.35(16) . . ? C22 C21 C26 118.83(17) . . ? C22 C21 N21 124.79(17) . . ? C26 C21 N21 116.36(16) . . ? C21 C22 C23 120.69(17) . . ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 . . ? C24 C23 C22 118.70(17) . . ? C24 C23 C27 123.21(17) . . ? C22 C23 C27 118.09(17) . . ? C23 C24 C25 122.08(17) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C26 C25 C24 117.32(17) . . ? C26 C25 C18 122.01(16) . . ? C24 C25 C18 120.66(16) . . ? C25 C26 O6 123.99(16) . . ? C25 C26 C21 122.36(16) . . ? O6 C26 C21 113.65(15) . . ? C273 C27 C272 109.47(19) . . ? C273 C27 C23 112.26(16) . . ? C272 C27 C23 108.48(17) . . ? C273 C27 C271 108.12(18) . . ? C272 C27 C271 108.89(18) . . ? C23 C27 C271 109.58(17) . . ? C32 C31 C36 119.03(18) . . ? C32 C31 N12 118.52(17) . . ? C36 C31 N12 122.43(18) . . ? C33 C32 C31 120.91(18) . . ? C33 C32 O3 124.23(18) . . ? C31 C32 O3 114.82(16) . . ? C32 C33 C34 119.7(2) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 119.92(19) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 120.3(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 120.1(2) . . ? C31 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C42 C41 C46 117.96(17) . . ? C42 C41 N22 118.69(16) . . ? C46 C41 N22 123.23(17) . . ? C43 C42 C41 121.46(17) . . ? C43 C42 O4 121.56(17) . . ? C41 C42 O4 116.73(16) . . ? C42 C43 C44 120.22(19) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C45 C44 C43 119.04(19) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C46 121.04(18) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C45 C46 C41 120.27(19) . . ? C45 C46 H46 119.9 . . ? C41 C46 H46 119.9 . . ? C56 C51 O3 122.39(17) . . ? C56 C51 C52 121.70(18) . . ? O3 C51 C52 115.66(16) . . ? C53 C52 C51 118.45(17) . . ? C53 C52 N51 124.78(17) . . ? C51 C52 N51 116.71(17) . . ? C54 C53 C52 119.84(19) . . ? C54 C53 H53 120.1 . . ? C52 C53 H53 120.1 . . ? C55 C54 C53 120.8(2) . . ? C55 C54 H54 119.6 . . ? C53 C54 H54 119.6 . . ? C56 C55 C54 119.91(18) . . ? C56 C55 H55 120.0 . . ? C54 C55 H55 120.0 . . ? C55 C56 C51 119.18(19) . . ? C55 C56 H56 120.4 . . ? C51 C56 H56 120.4 . . ? C66 C61 O4 123.85(17) . . ? C66 C61 C62 121.72(18) . . ? O4 C61 C62 114.39(15) . . ? C63 C62 C61 118.59(17) . . ? C63 C62 N52 125.39(17) . . ? C61 C62 N52 116.02(16) . . ? C62 C63 C64 119.21(19) . . ? C62 C63 H63 120.4 . . ? C64 C63 H63 120.4 . . ? C65 C64 C63 121.5(2) . . ? C65 C64 H64 119.3 . . ? C63 C64 H64 119.3 . . ? C64 C65 C66 119.87(18) . . ? C64 C65 H65 120.1 . . ? C66 C65 H65 120.1 . . ? C61 C66 C65 119.14(19) . . ? C61 C66 H66 120.4 . . ? C65 C66 H66 120.4 . . ? C17 C171 H17A 109.5 . . ? C17 C171 H17B 109.5 . . ? H17A C171 H17B 109.5 . . ? C17 C171 H17C 109.5 . . ? H17A C171 H17C 109.5 . . ? H17B C171 H17C 109.5 . . ? C17 C172 H17D 109.5 . . ? C17 C172 H17E 109.5 . . ? H17D C172 H17E 109.5 . . ? C17 C172 H17F 109.5 . . ? H17D C172 H17F 109.5 . . ? H17E C172 H17F 109.5 . . ? C17 C173 H17G 109.5 . . ? C17 C173 H17H 109.5 . . ? H17G C173 H17H 109.5 . . ? C17 C173 H17I 109.5 . . ? H17G C173 H17I 109.5 . . ? H17H C173 H17I 109.5 . . ? C18 C181 H18A 109.5 . . ? C18 C181 H18B 109.5 . . ? H18A C181 H18B 109.5 . . ? C18 C181 H18C 109.5 . . ? H18A C181 H18C 109.5 . . ? H18B C181 H18C 109.5 . . ? C18 C182 H18D 109.5 . . ? C18 C182 H18E 109.5 . . ? H18D C182 H18E 109.5 . . ? C18 C182 H18F 109.5 . . ? H18D C182 H18F 109.5 . . ? H18E C182 H18F 109.5 . . ? C27 C271 H27A 109.5 . . ? C27 C271 H27B 109.5 . . ? H27A C271 H27B 109.5 . . ? C27 C271 H27C 109.5 . . ? H27A C271 H27C 109.5 . . ? H27B C271 H27C 109.5 . . ? C27 C272 H27D 109.5 . . ? C27 C272 H27E 109.5 . . ? H27D C272 H27E 109.5 . . ? C27 C272 H27F 109.5 . . ? H27D C272 H27F 109.5 . . ? H27E C272 H27F 109.5 . . ? C27 C273 H27G 109.5 . . ? C27 C273 H27H 109.5 . . ? H27G C273 H27H 109.5 . . ? C27 C273 H27I 109.5 . . ? H27G C273 H27I 109.5 . . ? H27H C273 H27I 109.5 . . ? O1S S1 C2S 105.56(10) . . ? O1S S1 C1S 105.49(10) . . ? C2S S1 C1S 98.25(12) . . ? S1 C1S H1S1 109.5 . . ? S1 C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? S1 C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? S1 C2S H2S1 109.5 . . ? S1 C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? S1 C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? O2S S2 C4S 105.57(13) . . ? O2S S2 C3S 105.68(11) . . ? C4S S2 C3S 97.60(14) . . ? S2 C3S H3S1 109.5 . . ? S2 C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? S2 C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? S2 C4S H4S1 109.5 . . ? S2 C4S H4S2 109.5 . . ? H4S1 C4S H4S2 109.5 . . ? S2 C4S H4S3 109.5 . . ? H4S1 C4S H4S3 109.5 . . ? H4S2 C4S H4S3 109.5 . . ? C1M O1M H1M 115(3) . . ? O1M C1M H1MA 109.5 . . ? O1M C1M H1MB 109.5 . . ? H1MA C1M H1MB 109.5 . . ? O1M C1M H1MC 109.4 . . ? H1MA C1M H1MC 109.4 . . ? H1MB C1M H1MC 109.4 . . ? 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 C31 N12 C1 O1 11.3(3) . . . . ? C31 N12 C1 N11 -169.61(17) . . . . ? C11 N11 C1 O1 -11.9(3) . . . . ? C11 N11 C1 N12 168.99(18) . . . . ? C21 N21 C2 O2 7.2(3) . . . . ? C21 N21 C2 N22 -172.42(17) . . . . ? C41 N22 C2 O2 3.3(3) . . . . ? C41 N22 C2 N21 -177.03(16) . . . . ? C62 N52 C5 O5 -5.0(3) . . . . ? C62 N52 C5 N51 175.37(18) . . . . ? C52 N51 C5 O5 -15.0(3) . . . . ? C52 N51 C5 N52 164.64(18) . . . . ? C1 N11 C11 C12 -28.1(3) . . . . ? C1 N11 C11 C16 153.85(18) . . . . ? C16 C11 C12 C13 -0.8(3) . . . . ? N11 C11 C12 C13 -178.84(18) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? C11 C12 C13 C17 179.24(18) . . . . ? C12 C13 C14 C15 -1.1(3) . . . . ? C17 C13 C14 C15 -178.94(19) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C13 C14 C15 C18 177.56(18) . . . . ? C14 C15 C16 O6 -179.76(17) . . . . ? C18 C15 C16 O6 3.0(3) . . . . ? C14 C15 C16 C11 0.3(3) . . . . ? C18 C15 C16 C11 -176.90(17) . . . . ? C26 O6 C16 C15 3.5(3) . . . . ? C26 O6 C16 C11 -176.54(16) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? N11 C11 C16 C15 178.07(17) . . . . ? C12 C11 C16 O6 179.99(16) . . . . ? N11 C11 C16 O6 -1.9(2) . . . . ? C12 C13 C17 C171 171.5(2) . . . . ? C14 C13 C17 C171 -10.7(3) . . . . ? C12 C13 C17 C172 -69.0(2) . . . . ? C14 C13 C17 C172 108.9(2) . . . . ? C12 C13 C17 C173 51.0(3) . . . . ? C14 C13 C17 C173 -131.2(2) . . . . ? C16 C15 C18 C25 -8.1(2) . . . . ? C14 C15 C18 C25 174.75(17) . . . . ? C16 C15 C18 C182 -129.69(19) . . . . ? C14 C15 C18 C182 53.1(2) . . . . ? C16 C15 C18 C181 111.5(2) . . . . ? C14 C15 C18 C181 -65.7(2) . . . . ? C2 N21 C21 C22 15.5(3) . . . . ? C2 N21 C21 C26 -166.31(18) . . . . ? C26 C21 C22 C23 -0.4(3) . . . . ? N21 C21 C22 C23 177.83(18) . . . . ? C21 C22 C23 C24 -1.1(3) . . . . ? C21 C22 C23 C27 178.07(18) . . . . ? C22 C23 C24 C25 1.5(3) . . . . ? C27 C23 C24 C25 -177.59(18) . . . . ? C23 C24 C25 C26 -0.5(3) . . . . ? C23 C24 C25 C18 -179.12(17) . . . . ? C182 C18 C25 C26 128.66(19) . . . . ? C15 C18 C25 C26 7.7(2) . . . . ? C181 C18 C25 C26 -111.2(2) . . . . ? C182 C18 C25 C24 -52.7(2) . . . . ? C15 C18 C25 C24 -173.74(17) . . . . ? C181 C18 C25 C24 67.4(2) . . . . ? C24 C25 C26 O6 179.23(17) . . . . ? C18 C25 C26 O6 -2.1(3) . . . . ? C24 C25 C26 C21 -1.1(3) . . . . ? C18 C25 C26 C21 177.57(17) . . . . ? C16 O6 C26 C25 -4.0(3) . . . . ? C16 O6 C26 C21 176.28(16) . . . . ? C22 C21 C26 C25 1.5(3) . . . . ? N21 C21 C26 C25 -176.85(17) . . . . ? C22 C21 C26 O6 -178.79(16) . . . . ? N21 C21 C26 O6 2.9(2) . . . . ? C24 C23 C27 C273 -4.0(3) . . . . ? C22 C23 C27 C273 176.89(19) . . . . ? C24 C23 C27 C272 117.1(2) . . . . ? C22 C23 C27 C272 -62.0(2) . . . . ? C24 C23 C27 C271 -124.1(2) . . . . ? C22 C23 C27 C271 56.7(2) . . . . ? C1 N12 C31 C32 129.7(2) . . . . ? C1 N12 C31 C36 -51.8(3) . . . . ? C36 C31 C32 C33 -3.1(3) . . . . ? N12 C31 C32 C33 175.49(19) . . . . ? C36 C31 C32 O3 179.05(19) . . . . ? N12 C31 C32 O3 -2.4(3) . . . . ? C51 O3 C32 C33 20.8(3) . . . . ? C51 O3 C32 C31 -161.37(17) . . . . ? C31 C32 C33 C34 1.7(3) . . . . ? O3 C32 C33 C34 179.42(19) . . . . ? C32 C33 C34 C35 0.9(3) . . . . ? C33 C34 C35 C36 -2.2(4) . . . . ? C32 C31 C36 C35 1.8(3) . . . . ? N12 C31 C36 C35 -176.7(2) . . . . ? C34 C35 C36 C31 0.9(4) . . . . ? C2 N22 C41 C42 -146.52(18) . . . . ? C2 N22 C41 C46 37.4(3) . . . . ? C46 C41 C42 C43 0.6(3) . . . . ? N22 C41 C42 C43 -175.68(17) . . . . ? C46 C41 C42 O4 175.07(16) . . . . ? N22 C41 C42 O4 -1.2(2) . . . . ? C61 O4 C42 C43 -63.7(2) . . . . ? C61 O4 C42 C41 121.87(18) . . . . ? C41 C42 C43 C44 -0.9(3) . . . . ? O4 C42 C43 C44 -175.06(18) . . . . ? C42 C43 C44 C45 0.5(3) . . . . ? C43 C44 C45 C46 0.1(3) . . . . ? C44 C45 C46 C41 -0.3(3) . . . . ? C42 C41 C46 C45 0.0(3) . . . . ? N22 C41 C46 C45 176.09(17) . . . . ? C32 O3 C51 C56 52.3(3) . . . . ? C32 O3 C51 C52 -133.33(17) . . . . ? C56 C51 C52 C53 -2.4(3) . . . . ? O3 C51 C52 C53 -176.75(17) . . . . ? C56 C51 C52 N51 -179.70(18) . . . . ? O3 C51 C52 N51 5.9(2) . . . . ? C5 N51 C52 C53 33.7(3) . . . . ? C5 N51 C52 C51 -149.11(19) . . . . ? C51 C52 C53 C54 0.0(3) . . . . ? N51 C52 C53 C54 177.13(19) . . . . ? C52 C53 C54 C55 1.7(3) . . . . ? C53 C54 C55 C56 -1.0(3) . . . . ? C54 C55 C56 C51 -1.3(3) . . . . ? O3 C51 C56 C55 177.01(18) . . . . ? C52 C51 C56 C55 3.0(3) . . . . ? C42 O4 C61 C66 -17.7(3) . . . . ? C42 O4 C61 C62 164.43(16) . . . . ? C66 C61 C62 C63 -1.5(3) . . . . ? O4 C61 C62 C63 176.43(17) . . . . ? C66 C61 C62 N52 178.93(18) . . . . ? O4 C61 C62 N52 -3.2(2) . . . . ? C5 N52 C62 C63 4.9(3) . . . . ? C5 N52 C62 C61 -175.52(18) . . . . ? C61 C62 C63 C64 1.3(3) . . . . ? N52 C62 C63 C64 -179.1(2) . . . . ? C62 C63 C64 C65 -0.3(3) . . . . ? C63 C64 C65 C66 -0.7(4) . . . . ? O4 C61 C66 C65 -177.21(19) . . . . ? C62 C61 C66 C65 0.5(3) . . . . ? C64 C65 C66 C61 0.6(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 N11 H11 O1S 0.92(3) 2.04(3) 2.951(2) 171(2) . N12 H12 O1S 0.89(3) 2.66(2) 3.375(2) 138.1(19) . N12 H12 O2S 0.89(3) 2.70(3) 3.353(3) 131.0(19) . N21 H21 O1S 0.85(3) 2.16(3) 2.969(2) 158(2) . N22 H22 O1S 0.91(2) 2.29(2) 3.122(2) 152.5(19) . N51 H51 O2S 0.84(3) 2.06(3) 2.876(2) 164(2) . N52 H52 O2S 0.88(2) 2.16(2) 2.979(2) 155(2) . O1M H1M O2 0.78(4) 1.99(4) 2.769(3) 173(4) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.211 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.045