# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Rita Delgado' _publ_contact_author_address ;Instituto de Tecnologia Qu\'imica e Biol\'ogica, UNL, Av. da Rep\'ublica - EAN, 2780-157 Oeiras, Portugal ; _publ_contact_author_email delgado@itqb.unl.pt _publ_contact_author_phone '(+351) 21 446 9737' _publ_contact_author_fax '(+351) 21 441 1277' loop_ _publ_author_name _publ_author_address R.Delgado ;Instituto de Tecnologia Qu\'imica e Biol\'ogica, UNL, Av. da Rep\'ublica - EAN, 2780-157 Oeiras, Portugal ; P.Mateus ;Instituto de Tecnologia Qu\'imica e Biol\'ogica, UNL, Av. da Rep\'ublica - EAN, 2780-157 Oeiras, Portugal ; V.Felix ;Departamento de Qu\'imica, CICECO, Universidade de Aveiro, 3810?193 Aveiro, Portugal ; P.Brandao ;Departamento de Qu\'imica, CICECO, and Sec\,c\~ao Aut\'onoma de Ci\^encias da Sa\'ude Universidade de Aveiro, 3810?193 Aveiro, Portugal ; data_f _database_code_depnum_ccdc_archive 'CCDC 877715' #TrackingRef '- n4o3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H63 N5 O3' _chemical_formula_weight 746.02 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' _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 11.9682(3) _cell_length_b 13.5050(3) _cell_length_c 14.0716(4) _cell_angle_alpha 91.8620(10) _cell_angle_beta 92.1060(10) _cell_angle_gamma 111.1350(10) _cell_volume 2117.42(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9971 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 51940 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 29.21 _reflns_number_total 11371 _reflns_number_gt 8954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Speck, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+0.6449P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11371 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.27433(8) 0.18159(7) 0.32561(7) 0.0302(2) Uani 1 d . . . C2 C 0.29700(11) 0.11583(10) 0.39524(10) 0.0294(3) Uani 1 d . . . H2A H 0.2919 0.1439 0.4601 0.035 Uiso 1 calc R . . H2B H 0.3781 0.1132 0.3893 0.035 Uiso 1 calc R . . C3 C 0.20263(11) 0.00680(10) 0.37692(9) 0.0259(3) Uani 1 d . . . C4 C 0.20155(12) -0.05346(12) 0.29510(10) 0.0332(3) Uani 1 d . . . H4 H 0.2654 -0.0286 0.2533 0.040 Uiso 1 calc R . . C5 C 0.10858(12) -0.14974(11) 0.27321(10) 0.0323(3) Uani 1 d . . . H5 H 0.1097 -0.1897 0.2167 0.039 Uiso 1 calc R . . C6 C 0.01398(11) -0.18847(10) 0.33277(9) 0.0268(3) Uani 1 d . . . C7 C 0.01755(12) -0.13008(11) 0.41644(10) 0.0326(3) Uani 1 d . . . H7 H -0.0445 -0.1563 0.4596 0.039 Uiso 1 calc R . . C8 C 0.11059(12) -0.03367(10) 0.43816(10) 0.0311(3) Uani 1 d . . . H8 H 0.1111 0.0051 0.4959 0.037 Uiso 1 calc R . . C9 C -0.09014(12) -0.28989(10) 0.30503(11) 0.0327(3) Uani 1 d . . . H9A H -0.0857 -0.3097 0.2373 0.039 Uiso 1 calc R . . H9B H -0.0837 -0.3478 0.3436 0.039 Uiso 1 calc R . . N10 N -0.20640(10) -0.27976(9) 0.31880(8) 0.0282(2) Uani 1 d . . . H10 H -0.2050(14) -0.2183(13) 0.2944(11) 0.034 Uiso 1 d . . . C11 C -0.30338(11) -0.36822(10) 0.27003(9) 0.0276(3) Uani 1 d . . . H11A H -0.2956 -0.4360 0.2875 0.033 Uiso 1 calc R . . H11B H -0.2961 -0.3627 0.2004 0.033 Uiso 1 calc R . . C12 C -0.42612(11) -0.36954(10) 0.29532(9) 0.0275(3) Uani 1 d . . . H12A H -0.4872 -0.4388 0.2728 0.033 Uiso 1 calc R . . H12B H -0.4283 -0.3640 0.3655 0.033 Uiso 1 calc R . . N13 N -0.45893(9) -0.28389(8) 0.25490(7) 0.0242(2) Uani 1 d . . . C14 C -0.55535(11) -0.26992(10) 0.30890(9) 0.0286(3) Uani 1 d . . . H14A H -0.6137 -0.3405 0.3231 0.034 Uiso 1 calc R . . H14B H -0.5980 -0.2339 0.2695 0.034 Uiso 1 calc R . . C15 C -0.50722(13) -0.20462(11) 0.40191(10) 0.0324(3) Uani 1 d . . . H15A H -0.5760 -0.2004 0.4366 0.039 Uiso 1 calc R . . H15B H -0.4675 -0.2428 0.4416 0.039 Uiso 1 calc R . . N16 N -0.42256(10) -0.09696(9) 0.39170(8) 0.0303(2) Uani 1 d . . . H16 H -0.3622(15) -0.0997(13) 0.3534(12) 0.036 Uiso 1 d . . . C17 C -0.47658(13) -0.02743(11) 0.34927(12) 0.0380(3) Uani 1 d . . . H17A H -0.5489 -0.0318 0.3835 0.046 Uiso 1 calc R . . H17B H -0.5022 -0.0519 0.2822 0.046 Uiso 1 calc R . . C18 C -0.39056(12) 0.08720(11) 0.35273(10) 0.0305(3) Uani 1 d . . . C19 C -0.39619(13) 0.15476(12) 0.28255(12) 0.0385(3) Uani 1 d . . . H19 H -0.4556 0.1291 0.2319 0.046 Uiso 1 calc R . . C20 C -0.31663(14) 0.25948(12) 0.28474(12) 0.0401(3) Uani 1 d . . . H20 H -0.3218 0.3043 0.2354 0.048 Uiso 1 calc R . . C21 C -0.22981(12) 0.29912(11) 0.35820(11) 0.0346(3) Uani 1 d . . . C22 C -0.22523(13) 0.23184(12) 0.42942(11) 0.0368(3) Uani 1 d . . . H22 H -0.1671 0.2577 0.4809 0.044 Uiso 1 calc R . . C23 C -0.30435(13) 0.12746(11) 0.42642(10) 0.0336(3) Uani 1 d . . . H23 H -0.2994 0.0827 0.4758 0.040 Uiso 1 calc R . . C24 C -0.13372(13) 0.40719(11) 0.35548(13) 0.0416(4) Uani 1 d . . . H24A H -0.1623 0.4545 0.3173 0.050 Uiso 1 calc R . . H24B H -0.1097 0.4398 0.4206 0.050 Uiso 1 calc R . . O25 O -0.03631(8) 0.39036(7) 0.31283(8) 0.0360(2) Uani 1 d . . . C26 C 0.07073(11) 0.48311(10) 0.31171(10) 0.0298(3) Uani 1 d . . . H26A H 0.1000 0.5120 0.3773 0.036 Uiso 1 calc R . . H26B H 0.0561 0.5390 0.2750 0.036 Uiso 1 calc R . . C27 C 0.15980(10) 0.44502(9) 0.26437(9) 0.0240(2) Uani 1 d . . . C28 C 0.16702(10) 0.44696(9) 0.16550(9) 0.0233(2) Uani 1 d . . . C29 C 0.09450(11) 0.49778(10) 0.10712(10) 0.0288(3) Uani 1 d . . . H29A H 0.0157 0.4825 0.1352 0.035 Uiso 1 calc R . . H29B H 0.0797 0.4653 0.0416 0.035 Uiso 1 calc R . . C30 C 0.15716(14) 0.61809(11) 0.10271(12) 0.0387(3) Uani 1 d . . . H30A H 0.1806 0.6499 0.1674 0.046 Uiso 1 calc R . . H30B H 0.1023 0.6480 0.0722 0.046 Uiso 1 calc R . . H30C H 0.2288 0.6335 0.0657 0.046 Uiso 1 calc R . . C31 C 0.24128(10) 0.40135(9) 0.12058(8) 0.0223(2) Uani 1 d . . . C32 C 0.30757(10) 0.35356(9) 0.17478(9) 0.0215(2) Uani 1 d . . . C33 C 0.39099(11) 0.30674(10) 0.12787(9) 0.0252(2) Uani 1 d . . . H33A H 0.3570 0.2766 0.0636 0.030 Uiso 1 calc R . . H33B H 0.3971 0.2482 0.1658 0.030 Uiso 1 calc R . . C34 C 0.51614(11) 0.39051(11) 0.11970(11) 0.0336(3) Uani 1 d . . . H34A H 0.5104 0.4482 0.0817 0.040 Uiso 1 calc R . . H34B H 0.5674 0.3580 0.0887 0.040 Uiso 1 calc R . . H34C H 0.5509 0.4191 0.1834 0.040 Uiso 1 calc R . . C35 C 0.29779(10) 0.35099(9) 0.27407(8) 0.0221(2) Uani 1 d . . . C36 C 0.35701(11) 0.28917(10) 0.33206(9) 0.0251(2) Uani 1 d . . . H36A H 0.4343 0.2942 0.3057 0.030 Uiso 1 calc R . . H36B H 0.3720 0.3169 0.3992 0.030 Uiso 1 calc R . . C37 C 0.22295(10) 0.39512(9) 0.31908(9) 0.0237(2) Uani 1 d . . . C38 C 0.20884(12) 0.38824(11) 0.42571(9) 0.0313(3) Uani 1 d . . . H38A H 0.2163 0.3214 0.4463 0.038 Uiso 1 calc R . . H38B H 0.1276 0.3860 0.4401 0.038 Uiso 1 calc R . . C39 C 0.30264(14) 0.48253(13) 0.48196(10) 0.0390(3) Uani 1 d . . . H39A H 0.3832 0.4859 0.4670 0.047 Uiso 1 calc R . . H39B H 0.2923 0.4735 0.5503 0.047 Uiso 1 calc R . . H39C H 0.2924 0.5486 0.4646 0.047 Uiso 1 calc R . . C40 C 0.24256(11) 0.40074(10) 0.01268(9) 0.0268(3) Uani 1 d . . . H40A H 0.2597 0.4739 -0.0081 0.032 Uiso 1 calc R . . H40B H 0.3078 0.3776 -0.0082 0.032 Uiso 1 calc R . . O41 O 0.13086(8) 0.33161(7) -0.03201(6) 0.0296(2) Uani 1 d . . . C42 C 0.11287(12) 0.22150(11) -0.02576(11) 0.0350(3) Uani 1 d . . . H42A H 0.1618 0.2123 0.0292 0.042 Uiso 1 calc R . . H42B H 0.1396 0.1959 -0.0842 0.042 Uiso 1 calc R . . C43 C -0.01695(12) 0.15695(10) -0.01400(9) 0.0274(3) Uani 1 d . . . C44 C -0.07171(12) 0.05987(11) -0.06429(10) 0.0306(3) Uani 1 d . . . H44 H -0.0286 0.0374 -0.1103 0.037 Uiso 1 calc R . . C45 C -0.18872(12) -0.00450(11) -0.04800(10) 0.0327(3) Uani 1 d . . . H45 H -0.2249 -0.0703 -0.0834 0.039 Uiso 1 calc R . . C46 C -0.25322(12) 0.02595(11) 0.01909(10) 0.0328(3) Uani 1 d . . . C47 C -0.19946(14) 0.12381(12) 0.06786(11) 0.0374(3) Uani 1 d . . . H47 H -0.2431 0.1467 0.1131 0.045 Uiso 1 calc R . . C48 C -0.08258(13) 0.18868(11) 0.05134(10) 0.0336(3) Uani 1 d . . . H48 H -0.0474 0.2555 0.0853 0.040 Uiso 1 calc R . . C49 C -0.37802(13) -0.04705(12) 0.03952(12) 0.0396(3) Uani 1 d . . . H49A H -0.4147 -0.0087 0.0819 0.047 Uiso 1 calc R . . H49B H -0.4277 -0.0675 -0.0208 0.047 Uiso 1 calc R . . N50 N -0.37783(10) -0.14291(9) 0.08449(8) 0.0286(2) Uani 1 d . . . H50 H -0.3371(15) -0.1251(13) 0.1382(12) 0.034 Uiso 1 d . . . C51 C -0.49911(11) -0.21443(11) 0.10065(9) 0.0291(3) Uani 1 d . . . H51A H -0.5443 -0.2388 0.0387 0.035 Uiso 1 calc R . . H51B H -0.5404 -0.1757 0.1378 0.035 Uiso 1 calc R . . C52 C -0.49841(11) -0.31016(10) 0.15394(9) 0.0275(3) Uani 1 d . . . H52A H -0.5802 -0.3649 0.1496 0.033 Uiso 1 calc R . . H52B H -0.4444 -0.3408 0.1230 0.033 Uiso 1 calc R . . N100 N 0.82433(12) -0.03899(11) 0.26137(11) 0.0463(3) Uani 1 d . . . C100 C 0.89655(12) 0.04268(11) 0.27466(10) 0.0320(3) Uani 1 d . . . C101 C 0.98872(14) 0.14710(12) 0.29237(13) 0.0435(4) Uani 1 d . . . H10A H 0.9551 0.2017 0.2786 0.052 Uiso 1 calc R . . H10B H 1.0553 0.1546 0.2512 0.052 Uiso 1 calc R . . H10C H 1.0180 0.1556 0.3592 0.052 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0311(5) 0.0203(4) 0.0356(5) 0.0081(4) -0.0085(4) 0.0052(4) C2 0.0269(6) 0.0264(6) 0.0336(7) 0.0101(5) -0.0038(5) 0.0080(5) C3 0.0239(6) 0.0232(6) 0.0313(6) 0.0080(5) -0.0030(5) 0.0092(5) C4 0.0299(6) 0.0373(7) 0.0302(7) 0.0077(6) 0.0058(5) 0.0087(6) C5 0.0346(7) 0.0336(7) 0.0291(7) -0.0002(5) 0.0008(5) 0.0129(6) C6 0.0264(6) 0.0218(6) 0.0339(7) 0.0027(5) -0.0018(5) 0.0111(5) C7 0.0300(6) 0.0258(6) 0.0395(7) 0.0017(5) 0.0096(5) 0.0062(5) C8 0.0314(6) 0.0253(6) 0.0354(7) -0.0013(5) 0.0043(5) 0.0090(5) C9 0.0293(6) 0.0233(6) 0.0458(8) -0.0025(5) -0.0012(6) 0.0108(5) N10 0.0265(5) 0.0210(5) 0.0364(6) 0.0007(4) -0.0009(4) 0.0081(4) C11 0.0286(6) 0.0222(6) 0.0313(6) 0.0014(5) -0.0005(5) 0.0086(5) C12 0.0276(6) 0.0217(6) 0.0304(6) 0.0044(5) 0.0028(5) 0.0053(5) N13 0.0235(5) 0.0222(5) 0.0253(5) 0.0013(4) 0.0022(4) 0.0062(4) C14 0.0236(6) 0.0263(6) 0.0335(7) 0.0012(5) 0.0049(5) 0.0056(5) C15 0.0367(7) 0.0269(7) 0.0322(7) 0.0021(5) 0.0077(5) 0.0095(6) N16 0.0310(6) 0.0243(5) 0.0359(6) 0.0019(4) 0.0034(5) 0.0101(5) C17 0.0294(7) 0.0311(7) 0.0526(9) 0.0065(6) 0.0001(6) 0.0099(6) C18 0.0286(6) 0.0285(7) 0.0398(7) 0.0049(5) 0.0098(5) 0.0156(5) C19 0.0350(7) 0.0353(8) 0.0471(9) 0.0072(6) 0.0005(6) 0.0149(6) C20 0.0393(8) 0.0325(7) 0.0544(9) 0.0157(7) 0.0081(7) 0.0183(6) C21 0.0286(6) 0.0264(7) 0.0540(9) 0.0037(6) 0.0144(6) 0.0151(5) C22 0.0340(7) 0.0353(8) 0.0416(8) -0.0019(6) 0.0041(6) 0.0134(6) C23 0.0361(7) 0.0316(7) 0.0360(7) 0.0063(6) 0.0097(6) 0.0146(6) C24 0.0326(7) 0.0275(7) 0.0700(11) 0.0050(7) 0.0183(7) 0.0154(6) O25 0.0271(5) 0.0243(5) 0.0575(7) 0.0026(4) 0.0144(4) 0.0095(4) C26 0.0277(6) 0.0247(6) 0.0387(7) 0.0041(5) 0.0076(5) 0.0105(5) C27 0.0204(5) 0.0183(5) 0.0319(6) 0.0030(5) 0.0036(4) 0.0049(4) C28 0.0197(5) 0.0182(5) 0.0297(6) 0.0047(4) -0.0002(4) 0.0040(4) C29 0.0252(6) 0.0272(6) 0.0349(7) 0.0051(5) -0.0032(5) 0.0108(5) C30 0.0405(8) 0.0269(7) 0.0501(9) 0.0082(6) -0.0092(6) 0.0142(6) C31 0.0206(5) 0.0181(5) 0.0249(6) 0.0036(4) 0.0002(4) 0.0029(4) C32 0.0186(5) 0.0156(5) 0.0276(6) 0.0018(4) 0.0008(4) 0.0029(4) C33 0.0242(6) 0.0223(6) 0.0286(6) -0.0013(5) 0.0004(5) 0.0082(5) C34 0.0244(6) 0.0332(7) 0.0415(8) -0.0054(6) 0.0045(5) 0.0087(5) C35 0.0193(5) 0.0175(5) 0.0265(6) 0.0038(4) -0.0004(4) 0.0030(4) C36 0.0234(5) 0.0215(6) 0.0291(6) 0.0045(5) -0.0016(5) 0.0064(5) C37 0.0215(5) 0.0202(6) 0.0264(6) 0.0044(4) 0.0033(4) 0.0036(4) C38 0.0327(7) 0.0360(7) 0.0281(6) 0.0102(5) 0.0090(5) 0.0142(6) C39 0.0479(8) 0.0475(9) 0.0236(6) 0.0003(6) 0.0028(6) 0.0198(7) C40 0.0267(6) 0.0234(6) 0.0264(6) 0.0049(5) 0.0010(5) 0.0040(5) O41 0.0312(5) 0.0246(5) 0.0295(5) 0.0019(4) -0.0058(4) 0.0065(4) C42 0.0311(7) 0.0249(7) 0.0468(8) -0.0020(6) -0.0031(6) 0.0084(5) C43 0.0310(6) 0.0235(6) 0.0269(6) 0.0039(5) -0.0041(5) 0.0092(5) C44 0.0339(7) 0.0279(6) 0.0288(6) -0.0002(5) -0.0022(5) 0.0104(5) C45 0.0340(7) 0.0242(6) 0.0368(7) 0.0023(5) -0.0063(5) 0.0073(5) C46 0.0323(7) 0.0286(7) 0.0389(7) 0.0141(6) -0.0003(5) 0.0118(6) C47 0.0437(8) 0.0321(7) 0.0396(8) 0.0075(6) 0.0099(6) 0.0165(6) C48 0.0423(8) 0.0249(6) 0.0327(7) 0.0015(5) 0.0012(6) 0.0111(6) C49 0.0314(7) 0.0351(8) 0.0541(9) 0.0175(7) 0.0026(6) 0.0131(6) N50 0.0260(5) 0.0266(6) 0.0315(6) 0.0063(4) -0.0005(4) 0.0074(4) C51 0.0263(6) 0.0300(7) 0.0292(6) 0.0032(5) -0.0002(5) 0.0083(5) C52 0.0272(6) 0.0233(6) 0.0279(6) -0.0012(5) -0.0009(5) 0.0048(5) N100 0.0404(7) 0.0341(7) 0.0575(9) 0.0058(6) -0.0056(6) 0.0058(6) C100 0.0297(6) 0.0308(7) 0.0372(7) 0.0031(5) 0.0004(5) 0.0131(6) C101 0.0363(8) 0.0303(7) 0.0591(10) -0.0012(7) -0.0078(7) 0.0077(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.4259(14) . ? O1 C36 1.4304(14) . ? C2 C3 1.5050(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.3851(19) . ? C3 C8 1.3860(18) . ? C4 C5 1.3889(19) . ? C4 H4 0.9500 . ? C5 C6 1.3889(19) . ? C5 H5 0.9500 . ? C6 C7 1.3863(19) . ? C6 C9 1.5100(18) . ? C7 C8 1.3901(18) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N10 1.4655(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N10 C11 1.4607(16) . ? N10 H10 0.904(17) . ? C11 C12 1.5182(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N13 1.4730(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N13 C14 1.4687(16) . ? N13 C52 1.4711(16) . ? C14 C15 1.5250(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N16 1.4571(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? N16 C17 1.4497(18) . ? N16 H16 0.927(17) . ? C17 C18 1.5169(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.382(2) . ? C18 C23 1.384(2) . ? C19 C20 1.390(2) . ? C19 H19 0.9500 . ? C20 C21 1.385(2) . ? C20 H20 0.9500 . ? C21 C22 1.387(2) . ? C21 C24 1.500(2) . ? C22 C23 1.384(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O25 1.4159(16) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? O25 C26 1.4339(16) . ? C26 C27 1.5067(17) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.3975(17) . ? C27 C37 1.4058(17) . ? C28 C31 1.4070(17) . ? C28 C29 1.5210(16) . ? C29 C30 1.5288(19) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.4088(16) . ? C31 C40 1.5187(17) . ? C32 C35 1.4069(17) . ? C32 C33 1.5194(16) . ? C33 C34 1.5283(17) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C37 1.4002(17) . ? C35 C36 1.5145(16) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.5182(17) . ? C38 C39 1.532(2) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 O41 1.4333(15) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? O41 C42 1.4298(16) . ? C42 C43 1.5009(19) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C48 1.3843(19) . ? C43 C44 1.3912(18) . ? C44 C45 1.3885(19) . ? C44 H44 0.9500 . ? C45 C46 1.383(2) . ? C45 H45 0.9500 . ? C46 C47 1.388(2) . ? C46 C49 1.508(2) . ? C47 C48 1.390(2) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 N50 1.4600(17) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? N50 C51 1.4556(16) . ? N50 H50 0.862(17) . ? C51 C52 1.5180(18) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? N100 C100 1.1340(18) . ? C100 C101 1.450(2) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 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 C2 O1 C36 114.27(9) . . ? O1 C2 C3 106.62(10) . . ? O1 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C4 C3 C8 118.06(12) . . ? C4 C3 C2 120.61(12) . . ? C8 C3 C2 121.23(12) . . ? C3 C4 C5 120.99(12) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 120.97(13) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 117.94(12) . . ? C7 C6 C9 121.72(12) . . ? C5 C6 C9 120.32(12) . . ? C6 C7 C8 120.95(12) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C3 C8 C7 121.00(13) . . ? C3 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? N10 C9 C6 112.43(10) . . ? N10 C9 H9A 109.1 . . ? C6 C9 H9A 109.1 . . ? N10 C9 H9B 109.1 . . ? C6 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 N10 C9 110.80(10) . . ? C11 N10 H10 109.0(10) . . ? C9 N10 H10 108.4(10) . . ? N10 C11 C12 112.07(10) . . ? N10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N13 C12 C11 114.42(10) . . ? N13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? N13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 N13 C52 110.20(10) . . ? C14 N13 C12 109.13(10) . . ? C52 N13 C12 110.16(10) . . ? N13 C14 C15 111.85(10) . . ? N13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N16 C15 C14 115.31(11) . . ? N16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? N16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C17 N16 C15 113.53(11) . . ? C17 N16 H16 108.0(10) . . ? C15 N16 H16 109.0(10) . . ? N16 C17 C18 112.00(11) . . ? N16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C23 117.96(13) . . ? C19 C18 C17 121.00(13) . . ? C23 C18 C17 121.04(13) . . ? C18 C19 C20 121.23(14) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C21 C20 C19 120.58(14) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 118.23(13) . . ? C20 C21 C24 121.23(14) . . ? C22 C21 C24 120.13(14) . . ? C23 C22 C21 120.83(14) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C18 C23 C22 121.16(13) . . ? C18 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? O25 C24 C21 105.51(11) . . ? O25 C24 H24A 110.6 . . ? C21 C24 H24A 110.6 . . ? O25 C24 H24B 110.6 . . ? C21 C24 H24B 110.6 . . ? H24A C24 H24B 108.8 . . ? C24 O25 C26 114.75(10) . . ? O25 C26 C27 104.65(10) . . ? O25 C26 H26A 110.8 . . ? C27 C26 H26A 110.8 . . ? O25 C26 H26B 110.8 . . ? C27 C26 H26B 110.8 . . ? H26A C26 H26B 108.9 . . ? C28 C27 C37 120.74(11) . . ? C28 C27 C26 119.77(11) . . ? C37 C27 C26 118.95(11) . . ? C27 C28 C31 119.60(11) . . ? C27 C28 C29 120.00(11) . . ? C31 C28 C29 120.41(11) . . ? C28 C29 C30 112.87(10) . . ? C28 C29 H29A 109.0 . . ? C30 C29 H29A 109.0 . . ? C28 C29 H29B 109.0 . . ? C30 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 C32 120.27(11) . . ? C28 C31 C40 118.02(10) . . ? C32 C31 C40 121.64(11) . . ? C35 C32 C31 119.32(11) . . ? C35 C32 C33 119.65(10) . . ? C31 C32 C33 121.02(11) . . ? C32 C33 C34 111.54(10) . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C37 C35 C32 120.69(11) . . ? C37 C35 C36 118.93(11) . . ? C32 C35 C36 120.01(10) . . ? O1 C36 C35 105.50(9) . . ? O1 C36 H36A 110.6 . . ? C35 C36 H36A 110.6 . . ? O1 C36 H36B 110.6 . . ? C35 C36 H36B 110.6 . . ? H36A C36 H36B 108.8 . . ? C35 C37 C27 119.34(11) . . ? C35 C37 C38 120.49(11) . . ? C27 C37 C38 120.17(11) . . ? C37 C38 C39 112.19(11) . . ? C37 C38 H38A 109.2 . . ? C39 C38 H38A 109.2 . . ? C37 C38 H38B 109.2 . . ? C39 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O41 C40 C31 112.21(10) . . ? O41 C40 H40A 109.2 . . ? C31 C40 H40A 109.2 . . ? O41 C40 H40B 109.2 . . ? C31 C40 H40B 109.2 . . ? H40A C40 H40B 107.9 . . ? C42 O41 C40 113.07(10) . . ? O41 C42 C43 110.78(11) . . ? O41 C42 H42A 109.5 . . ? C43 C42 H42A 109.5 . . ? O41 C42 H42B 109.5 . . ? C43 C42 H42B 109.5 . . ? H42A C42 H42B 108.1 . . ? C48 C43 C44 118.43(13) . . ? C48 C43 C42 121.10(12) . . ? C44 C43 C42 120.32(12) . . ? C45 C44 C43 120.72(13) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C46 C45 C44 120.83(13) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C45 C46 C47 118.44(13) . . ? C45 C46 C49 120.30(13) . . ? C47 C46 C49 121.25(14) . . ? C46 C47 C48 120.85(14) . . ? C46 C47 H47 119.6 . . ? C48 C47 H47 119.6 . . ? C43 C48 C47 120.69(13) . . ? C43 C48 H48 119.7 . . ? C47 C48 H48 119.7 . . ? N50 C49 C46 112.03(11) . . ? N50 C49 H49A 109.2 . . ? C46 C49 H49A 109.2 . . ? N50 C49 H49B 109.2 . . ? C46 C49 H49B 109.2 . . ? H49A C49 H49B 107.9 . . ? C51 N50 C49 111.45(10) . . ? C51 N50 H50 109.3(11) . . ? C49 N50 H50 109.1(11) . . ? N50 C51 C52 111.40(10) . . ? N50 C51 H51A 109.3 . . ? C52 C51 H51A 109.3 . . ? N50 C51 H51B 109.3 . . ? C52 C51 H51B 109.3 . . ? H51A C51 H51B 108.0 . . ? N13 C52 C51 112.86(10) . . ? N13 C52 H52A 109.0 . . ? C51 C52 H52A 109.0 . . ? N13 C52 H52B 109.0 . . ? C51 C52 H52B 109.0 . . ? H52A C52 H52B 107.8 . . ? N100 C100 C101 179.59(17) . . ? C100 C101 H10A 109.5 . . ? C100 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C100 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.21 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.403 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.046