# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jeremy Sanders' _publ_contact_author_email jkms@cam.ac.uk _publ_author_name 'Jeremy Sanders' data_js1103 _database_code_depnum_ccdc_archive 'CCDC 827938' #TrackingRef '- js1103.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H50 N10 O12, C H4 O' _chemical_formula_sum 'C53 H54 N10 O13' _chemical_formula_weight 1039.06 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.3728(2) _cell_length_b 14.5231(2) _cell_length_c 14.9321(3) _cell_angle_alpha 66.0970(10) _cell_angle_beta 62.0950(10) _cell_angle_gamma 73.9140(10) _cell_volume 2503.44(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 36673 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 41062 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11435 _reflns_number_gt 7350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+1.2205P] 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 11435 _refine_ls_number_parameters 688 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 O1 O 0.56913(13) 0.60416(11) -0.37528(12) 0.0473(4) Uani 1 1 d . . . O2 O 0.70022(19) 0.64949(13) -0.00176(17) 0.0741(6) Uani 1 1 d . . . O3 O 0.67383(13) 0.36345(11) 0.22425(13) 0.0479(4) Uani 1 1 d . . . O4 O 0.68815(12) 0.20661(11) 0.15634(12) 0.0419(4) Uani 1 1 d . . . O5 O 0.81414(11) 0.06923(11) 0.04300(11) 0.0371(3) Uani 1 1 d . . . O6 O 0.98754(12) -0.02564(12) 0.23096(12) 0.0447(4) Uani 1 1 d . . . O7 O 0.91763(16) 0.58213(13) -0.18248(17) 0.0669(5) Uani 1 1 d . . . O8 O 0.84994(16) 0.34610(14) -0.46373(14) 0.0631(5) Uani 1 1 d . . . O9 O 0.81944(12) 0.04819(12) -0.28457(11) 0.0417(4) Uani 1 1 d . . . O10 O 0.66563(11) -0.03196(10) -0.06660(11) 0.0365(3) Uani 1 1 d . . . O11 O 0.57720(11) -0.07667(10) -0.17227(11) 0.0375(3) Uani 1 1 d . . . O12 O 0.54784(15) 0.16867(13) -0.42650(14) 0.0572(5) Uani 1 1 d . . . N1 N 0.61436(14) 0.33855(13) -0.14214(14) 0.0383(4) Uani 1 1 d . . . N2 N 0.64932(14) 0.50870(14) -0.04631(14) 0.0407(4) Uani 1 1 d . . . N3 N 0.67154(15) 0.48926(14) 0.04004(14) 0.0413(4) Uani 1 1 d . . . H3N H 0.6690 0.4274 0.0860 0.050 Uiso 1 1 calc R . . N4 N 0.93767(14) 0.11004(13) 0.11178(14) 0.0376(4) Uani 1 1 d . . . H4N H 0.9113 0.1326 0.0631 0.045 Uiso 1 1 calc R . . N5 N 0.98394(15) 0.17176(15) 0.12465(15) 0.0430(4) Uani 1 1 d . . . N6 N 0.93988(14) 0.26824(13) -0.07022(14) 0.0393(4) Uani 1 1 d . . . N7 N 0.88812(15) 0.29380(14) -0.28861(14) 0.0420(4) Uani 1 1 d . . . N8 N 0.88370(15) 0.22376(15) -0.32609(14) 0.0447(5) Uani 1 1 d . . . H8N H 0.8935 0.1585 -0.2927 0.054 Uiso 1 1 calc R . . N9 N 0.58379(14) 0.12176(13) -0.28074(14) 0.0387(4) Uani 1 1 d . . . H9N H 0.5957 0.0716 -0.2279 0.046 Uiso 1 1 calc R . . N10 N 0.57732(14) 0.22045(13) -0.28762(15) 0.0395(4) Uani 1 1 d . . . C1 C 0.5559(2) 0.60039(18) -0.46260(19) 0.0510(6) Uani 1 1 d . . . H1B H 0.5452 0.6695 -0.5089 0.077 Uiso 1 1 calc R . . H1C H 0.4940 0.5651 -0.4349 0.077 Uiso 1 1 calc R . . H1D H 0.6192 0.5640 -0.5039 0.077 Uiso 1 1 calc R . . C2 C 0.58197(17) 0.51480(16) -0.30097(17) 0.0383(5) Uani 1 1 d . . . C3 C 0.59693(17) 0.52029(16) -0.21754(18) 0.0398(5) Uani 1 1 d . . . H3 H 0.5958 0.5841 -0.2131 0.048 Uiso 1 1 calc R . . C4 C 0.61345(16) 0.43154(16) -0.14150(17) 0.0377(5) Uani 1 1 d . . . C5 C 0.63474(17) 0.43021(17) -0.05406(18) 0.0417(5) Uani 1 1 d . . . H5 H 0.6378 0.3672 -0.0001 0.050 Uiso 1 1 calc R . . C6 C 0.69729(19) 0.56218(17) 0.05689(19) 0.0449(5) Uani 1 1 d . . . C7 C 0.72600(17) 0.52860(16) 0.15107(18) 0.0397(5) Uani 1 1 d . . . C8 C 0.76812(19) 0.59979(18) 0.1583(2) 0.0479(6) Uani 1 1 d . . . H8 H 0.7746 0.6654 0.1062 0.058 Uiso 1 1 calc R . . C9 C 0.8006(2) 0.5778(2) 0.2388(2) 0.0530(6) Uani 1 1 d . . . H9 H 0.8302 0.6274 0.2409 0.064 Uiso 1 1 calc R . . C10 C 0.7902(2) 0.4842(2) 0.3159(2) 0.0524(6) Uani 1 1 d . . . H10 H 0.8125 0.4690 0.3715 0.063 Uiso 1 1 calc R . . C11 C 0.7474(2) 0.41208(18) 0.31253(19) 0.0483(6) Uani 1 1 d . . . H11 H 0.7391 0.3477 0.3668 0.058 Uiso 1 1 calc R . . C12 C 0.71643(17) 0.43310(17) 0.23051(18) 0.0399(5) Uani 1 1 d . . . C13 C 0.6794(2) 0.25994(17) 0.29101(19) 0.0467(6) Uani 1 1 d . . . H13A H 0.6417 0.2547 0.3676 0.056 Uiso 1 1 calc R . . H13B H 0.7541 0.2312 0.2766 0.056 Uiso 1 1 calc R . . C14 C 0.6280(2) 0.20532(18) 0.26398(18) 0.0479(6) Uani 1 1 d . . . H14A H 0.6232 0.1344 0.3128 0.057 Uiso 1 1 calc R . . H14B H 0.5554 0.2382 0.2732 0.057 Uiso 1 1 calc R . . C15 C 0.64111(17) 0.15592(17) 0.12693(18) 0.0400(5) Uani 1 1 d . . . H15A H 0.5795 0.1997 0.1133 0.048 Uiso 1 1 calc R . . H15B H 0.6158 0.0928 0.1860 0.048 Uiso 1 1 calc R . . C16 C 0.72105(17) 0.13127(17) 0.02799(18) 0.0400(5) Uani 1 1 d . . . H16A H 0.6883 0.0949 0.0082 0.048 Uiso 1 1 calc R . . H16B H 0.7425 0.1950 -0.0318 0.048 Uiso 1 1 calc R . . C17 C 0.79741(16) -0.01935(16) 0.12765(16) 0.0349(5) Uani 1 1 d . . . C18 C 0.72316(18) -0.08042(17) 0.15311(18) 0.0414(5) Uani 1 1 d . . . H18 H 0.6833 -0.0606 0.1112 0.050 Uiso 1 1 calc R . . C19 C 0.70691(19) -0.16942(17) 0.23855(19) 0.0441(5) Uani 1 1 d . . . H19 H 0.6554 -0.2101 0.2559 0.053 Uiso 1 1 calc R . . C20 C 0.76592(19) -0.19909(17) 0.29871(19) 0.0462(6) Uani 1 1 d . . . H20 H 0.7551 -0.2603 0.3576 0.055 Uiso 1 1 calc R . . C21 C 0.84066(18) -0.13962(17) 0.27303(18) 0.0417(5) Uani 1 1 d . . . H21 H 0.8817 -0.1616 0.3141 0.050 Uiso 1 1 calc R . . C22 C 0.85764(16) -0.04826(16) 0.18849(16) 0.0351(5) Uani 1 1 d . . . C23 C 0.93424(16) 0.01200(16) 0.17771(16) 0.0361(5) Uani 1 1 d . . . C24 C 0.98613(19) 0.26547(19) 0.06646(19) 0.0458(6) Uani 1 1 d . . . H24 H 1.0127 0.3050 0.0850 0.055 Uiso 1 1 calc R . . C25 C 0.95476(17) 0.32237(17) -0.02378(18) 0.0410(5) Uani 1 1 d . . . C26 C 0.94621(19) 0.42692(18) -0.0604(2) 0.0485(6) Uani 1 1 d . . . H26 H 0.9561 0.4624 -0.0247 0.058 Uiso 1 1 calc R . . C27 C 0.92309(18) 0.47964(18) -0.1496(2) 0.0488(6) Uani 1 1 d . . . C28 C 0.8831(3) 0.6379(2) -0.2676(3) 0.0753(9) Uani 1 1 d . . . H28A H 0.8769 0.7106 -0.2804 0.113 Uiso 1 1 calc R . . H28B H 0.8140 0.6188 -0.2477 0.113 Uiso 1 1 calc R . . H28C H 0.9347 0.6224 -0.3329 0.113 Uiso 1 1 calc R . . C29 C 0.90919(17) 0.42612(17) -0.20011(19) 0.0437(5) Uani 1 1 d . . . H29 H 0.8935 0.4600 -0.2616 0.052 Uiso 1 1 calc R . . C30 C 0.91902(16) 0.32047(16) -0.15737(17) 0.0375(5) Uani 1 1 d . . . C31 C 0.90954(17) 0.25600(17) -0.20596(17) 0.0386(5) Uani 1 1 d . . . H31 H 0.9195 0.1845 -0.1754 0.046 Uiso 1 1 calc R . . C32 C 0.86405(18) 0.2564(2) -0.41557(18) 0.0464(6) Uani 1 1 d . . . C33 C 0.86702(17) 0.17522(19) -0.45477(17) 0.0444(6) Uani 1 1 d . . . C34 C 0.89185(19) 0.2046(2) -0.56419(19) 0.0547(7) Uani 1 1 d . . . H34 H 0.9033 0.2731 -0.6073 0.066 Uiso 1 1 calc R . . C35 C 0.90017(19) 0.1359(3) -0.6110(2) 0.0610(8) Uani 1 1 d . . . H35 H 0.9166 0.1574 -0.6854 0.073 Uiso 1 1 calc R . . C36 C 0.88468(19) 0.0370(2) -0.5497(2) 0.0572(7) Uani 1 1 d . . . H36 H 0.8915 -0.0101 -0.5822 0.069 Uiso 1 1 calc R . . C37 C 0.85911(18) 0.0048(2) -0.44052(19) 0.0506(6) Uani 1 1 d . . . H37 H 0.8483 -0.0640 -0.3986 0.061 Uiso 1 1 calc R . . C38 C 0.84938(16) 0.07408(19) -0.39273(17) 0.0420(5) Uani 1 1 d . . . C39 C 0.82408(17) -0.05717(17) -0.22266(17) 0.0401(5) Uani 1 1 d . . . H39A H 0.8985 -0.0883 -0.2440 0.048 Uiso 1 1 calc R . . H39B H 0.7840 -0.0931 -0.2349 0.048 Uiso 1 1 calc R . . C40 C 0.77663(17) -0.06529(17) -0.10670(17) 0.0394(5) Uani 1 1 d . . . H40A H 0.7881 -0.1368 -0.0638 0.047 Uiso 1 1 calc R . . H40B H 0.8140 -0.0244 -0.0972 0.047 Uiso 1 1 calc R . . C41 C 0.59906(17) -0.11166(16) -0.01383(17) 0.0376(5) Uani 1 1 d . . . H41A H 0.5253 -0.0845 0.0229 0.045 Uiso 1 1 calc R . . H41B H 0.6214 -0.1651 0.0416 0.045 Uiso 1 1 calc R . . C42 C 0.60169(18) -0.15830(16) -0.08848(17) 0.0386(5) Uani 1 1 d . . . H42A H 0.6727 -0.1939 -0.1190 0.046 Uiso 1 1 calc R . . H42B H 0.5489 -0.2077 -0.0497 0.046 Uiso 1 1 calc R . . C43 C 0.60405(16) -0.09214(16) -0.26645(17) 0.0352(5) Uani 1 1 d . . . C44 C 0.63756(17) -0.18776(17) -0.2784(2) 0.0431(5) Uani 1 1 d . . . H44 H 0.6456 -0.2450 -0.2210 0.052 Uiso 1 1 calc R . . C45 C 0.6590(2) -0.1992(2) -0.3737(2) 0.0547(7) Uani 1 1 d . . . H45 H 0.6835 -0.2642 -0.3822 0.066 Uiso 1 1 calc R . . C46 C 0.6452(2) -0.1170(2) -0.4569(2) 0.0604(7) Uani 1 1 d . . . H46 H 0.6575 -0.1256 -0.5215 0.072 Uiso 1 1 calc R . . C47 C 0.6132(2) -0.0222(2) -0.44520(19) 0.0507(6) Uani 1 1 d . . . H47 H 0.6038 0.0341 -0.5027 0.061 Uiso 1 1 calc R . . C48 C 0.59437(16) -0.00675(16) -0.35185(17) 0.0379(5) Uani 1 1 d . . . C49 C 0.57161(17) 0.10201(16) -0.35613(18) 0.0396(5) Uani 1 1 d . . . C50 C 0.60225(17) 0.23273(16) -0.22201(18) 0.0398(5) Uani 1 1 d . . . H50 H 0.6231 0.1753 -0.1724 0.048 Uiso 1 1 calc R . . C51 C 0.59908(16) 0.33511(15) -0.22242(17) 0.0366(5) Uani 1 1 d . . . C52 C 0.58283(17) 0.42056(16) -0.30351(17) 0.0386(5) Uani 1 1 d . . . H52 H 0.5726 0.4141 -0.3590 0.046 Uiso 1 1 calc R . . O13 O 0.8467(3) 0.5251(2) -0.4124(2) 0.1189(10) Uani 1 1 d . . . H13 H 0.8541 0.4652 -0.4110 0.143 Uiso 1 1 calc R . . C53 C 0.8742(3) 0.5859(3) -0.5114(3) 0.0947(11) Uani 1 1 d . . . H53A H 0.8792 0.6532 -0.5148 0.114 Uiso 1 1 calc R . . H53B H 0.8209 0.5908 -0.5371 0.114 Uiso 1 1 calc R . . H53C H 0.9430 0.5591 -0.5566 0.114 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0698(11) 0.0306(8) 0.0420(9) -0.0041(7) -0.0317(8) -0.0010(7) O2 0.1295(18) 0.0342(10) 0.0773(14) -0.0030(9) -0.0722(14) -0.0033(10) O3 0.0667(11) 0.0378(9) 0.0465(9) -0.0028(7) -0.0352(9) -0.0103(7) O4 0.0443(9) 0.0470(9) 0.0365(8) -0.0127(7) -0.0151(7) -0.0116(7) O5 0.0400(8) 0.0386(8) 0.0344(8) -0.0064(7) -0.0203(7) -0.0057(6) O6 0.0498(9) 0.0499(10) 0.0436(9) -0.0125(8) -0.0299(8) -0.0024(7) O7 0.0753(13) 0.0350(10) 0.0939(15) -0.0154(10) -0.0427(12) -0.0036(8) O8 0.0813(13) 0.0581(12) 0.0465(10) 0.0020(9) -0.0382(10) -0.0091(9) O9 0.0482(9) 0.0513(10) 0.0304(8) -0.0129(7) -0.0174(7) -0.0101(7) O10 0.0391(8) 0.0344(8) 0.0355(8) -0.0091(6) -0.0147(7) -0.0076(6) O11 0.0491(9) 0.0300(8) 0.0381(8) -0.0064(6) -0.0262(7) -0.0026(6) O12 0.0776(12) 0.0454(10) 0.0493(10) -0.0049(8) -0.0400(10) 0.0027(8) N1 0.0410(10) 0.0321(10) 0.0375(10) -0.0041(8) -0.0186(8) -0.0039(7) N2 0.0437(11) 0.0403(11) 0.0377(10) -0.0096(8) -0.0215(9) 0.0004(8) N3 0.0508(11) 0.0366(10) 0.0368(10) -0.0042(8) -0.0245(9) -0.0046(8) N4 0.0422(10) 0.0436(11) 0.0353(10) -0.0098(8) -0.0226(8) -0.0084(8) N5 0.0493(11) 0.0491(12) 0.0403(11) -0.0147(9) -0.0221(9) -0.0118(9) N6 0.0430(10) 0.0398(10) 0.0356(10) -0.0103(8) -0.0160(8) -0.0080(8) N7 0.0455(11) 0.0434(11) 0.0358(10) -0.0067(9) -0.0169(9) -0.0118(8) N8 0.0568(12) 0.0455(11) 0.0340(10) -0.0033(9) -0.0255(9) -0.0102(9) N9 0.0494(11) 0.0288(10) 0.0383(10) -0.0039(8) -0.0241(9) -0.0041(8) N10 0.0433(10) 0.0286(10) 0.0418(11) -0.0061(8) -0.0178(9) -0.0040(7) C1 0.0708(17) 0.0376(13) 0.0416(13) -0.0047(11) -0.0306(13) 0.0006(11) C2 0.0400(12) 0.0290(11) 0.0378(12) -0.0037(9) -0.0174(10) -0.0001(9) C3 0.0453(13) 0.0307(12) 0.0419(13) -0.0094(10) -0.0197(10) -0.0022(9) C4 0.0364(11) 0.0356(12) 0.0370(12) -0.0075(10) -0.0155(10) -0.0034(9) C5 0.0452(13) 0.0361(13) 0.0400(13) -0.0051(10) -0.0218(11) -0.0018(9) C6 0.0526(14) 0.0349(13) 0.0483(14) -0.0119(11) -0.0265(12) 0.0023(10) C7 0.0423(12) 0.0371(12) 0.0405(12) -0.0138(10) -0.0206(10) 0.0035(9) C8 0.0580(15) 0.0348(13) 0.0532(15) -0.0153(11) -0.0264(12) 0.0004(10) C9 0.0614(16) 0.0494(16) 0.0655(17) -0.0305(14) -0.0338(14) 0.0020(12) C10 0.0618(16) 0.0550(16) 0.0553(16) -0.0283(13) -0.0339(13) 0.0069(12) C11 0.0588(15) 0.0441(14) 0.0459(14) -0.0124(11) -0.0297(12) 0.0012(11) C12 0.0421(12) 0.0387(13) 0.0412(13) -0.0149(10) -0.0198(10) 0.0003(9) C13 0.0668(16) 0.0351(13) 0.0372(12) -0.0047(10) -0.0267(12) -0.0044(11) C14 0.0581(15) 0.0430(14) 0.0355(13) -0.0062(10) -0.0159(11) -0.0111(11) C15 0.0374(12) 0.0397(12) 0.0442(13) -0.0090(10) -0.0195(10) -0.0078(9) C16 0.0446(13) 0.0398(12) 0.0416(12) -0.0070(10) -0.0258(11) -0.0076(10) C17 0.0396(11) 0.0348(12) 0.0310(11) -0.0113(9) -0.0152(9) -0.0024(9) C18 0.0464(13) 0.0419(13) 0.0452(13) -0.0153(11) -0.0247(11) -0.0047(10) C19 0.0494(13) 0.0373(13) 0.0487(14) -0.0157(11) -0.0189(11) -0.0083(10) C20 0.0593(15) 0.0345(13) 0.0410(13) -0.0086(10) -0.0204(12) -0.0051(11) C21 0.0476(13) 0.0413(13) 0.0375(12) -0.0124(10) -0.0217(10) 0.0009(10) C22 0.0377(11) 0.0375(12) 0.0312(11) -0.0132(9) -0.0148(9) -0.0008(9) C23 0.0372(11) 0.0420(13) 0.0308(11) -0.0136(10) -0.0144(9) -0.0024(9) C24 0.0519(14) 0.0514(15) 0.0455(14) -0.0168(12) -0.0235(12) -0.0134(11) C25 0.0385(12) 0.0437(13) 0.0440(13) -0.0162(11) -0.0156(10) -0.0080(9) C26 0.0476(14) 0.0434(14) 0.0618(16) -0.0203(12) -0.0240(12) -0.0071(10) C27 0.0406(13) 0.0363(13) 0.0650(16) -0.0152(12) -0.0189(12) -0.0040(10) C28 0.081(2) 0.0369(15) 0.099(2) 0.0006(15) -0.0493(19) -0.0047(13) C29 0.0412(12) 0.0395(13) 0.0449(13) -0.0068(11) -0.0188(11) -0.0047(10) C30 0.0334(11) 0.0396(12) 0.0344(11) -0.0085(10) -0.0116(9) -0.0060(9) C31 0.0416(12) 0.0379(12) 0.0332(12) -0.0072(10) -0.0154(10) -0.0059(9) C32 0.0426(13) 0.0581(16) 0.0307(12) -0.0028(11) -0.0161(10) -0.0099(11) C33 0.0344(12) 0.0659(16) 0.0321(12) -0.0122(11) -0.0173(10) -0.0030(10) C34 0.0428(13) 0.0826(19) 0.0320(12) -0.0119(13) -0.0189(11) -0.0005(12) C35 0.0437(14) 0.108(2) 0.0324(13) -0.0261(16) -0.0188(11) 0.0021(14) C36 0.0404(14) 0.101(2) 0.0447(15) -0.0398(16) -0.0180(12) -0.0018(13) C37 0.0401(13) 0.0786(18) 0.0420(13) -0.0272(13) -0.0160(11) -0.0085(12) C38 0.0325(11) 0.0677(16) 0.0305(11) -0.0189(11) -0.0143(9) -0.0052(10) C39 0.0371(12) 0.0480(14) 0.0379(12) -0.0161(10) -0.0150(10) -0.0056(10) C40 0.0382(12) 0.0458(13) 0.0373(12) -0.0129(10) -0.0172(10) -0.0062(9) C41 0.0396(12) 0.0347(12) 0.0331(11) -0.0016(9) -0.0161(10) -0.0083(9) C42 0.0453(12) 0.0307(11) 0.0405(12) -0.0011(9) -0.0242(10) -0.0090(9) C43 0.0319(11) 0.0382(12) 0.0387(12) -0.0117(10) -0.0158(9) -0.0066(9) C44 0.0413(12) 0.0378(13) 0.0526(14) -0.0153(11) -0.0192(11) -0.0065(9) C45 0.0545(15) 0.0506(16) 0.0603(17) -0.0283(14) -0.0125(13) -0.0112(12) C46 0.0706(18) 0.0703(19) 0.0426(15) -0.0267(14) -0.0098(13) -0.0222(14) C47 0.0591(16) 0.0546(16) 0.0381(13) -0.0115(11) -0.0184(12) -0.0138(12) C48 0.0365(11) 0.0417(13) 0.0363(12) -0.0097(10) -0.0167(10) -0.0064(9) C49 0.0390(12) 0.0371(12) 0.0370(12) -0.0051(10) -0.0168(10) -0.0038(9) C50 0.0408(12) 0.0327(12) 0.0385(12) -0.0027(10) -0.0181(10) -0.0030(9) C51 0.0351(11) 0.0315(12) 0.0371(12) -0.0061(9) -0.0138(9) -0.0042(8) C52 0.0429(12) 0.0354(12) 0.0351(12) -0.0073(10) -0.0174(10) -0.0039(9) O13 0.167(3) 0.0840(18) 0.091(2) 0.0013(15) -0.0485(19) -0.0462(18) C53 0.109(3) 0.089(3) 0.063(2) -0.0083(19) -0.041(2) 0.008(2) _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 1.357(2) . ? O1 C1 1.427(3) . ? O2 C6 1.213(3) . ? O3 C12 1.371(3) . ? O3 C13 1.433(3) . ? O4 C15 1.417(2) . ? O4 C14 1.420(3) . ? O5 C17 1.371(2) . ? O5 C16 1.450(2) . ? O6 C23 1.226(2) . ? O7 C27 1.357(3) . ? O7 C28 1.432(3) . ? O8 C32 1.220(3) . ? O9 C38 1.372(2) . ? O9 C39 1.434(3) . ? O10 C41 1.430(2) . ? O10 C40 1.432(3) . ? O11 C43 1.370(2) . ? O11 C42 1.440(2) . ? O12 C49 1.219(3) . ? N1 C51 1.337(3) . ? N1 C4 1.351(3) . ? N2 C5 1.272(3) . ? N2 N3 1.373(2) . ? N3 C6 1.357(3) . ? N3 H3N 0.8800 . ? N4 C23 1.363(3) . ? N4 N5 1.368(2) . ? N4 H4N 0.8800 . ? N5 C24 1.284(3) . ? N6 C30 1.341(3) . ? N6 C25 1.348(3) . ? N7 C31 1.278(3) . ? N7 N8 1.372(3) . ? N8 C32 1.362(3) . ? N8 H8N 0.8800 . ? N9 C49 1.362(3) . ? N9 N10 1.374(2) . ? N9 H9N 0.8800 . ? N10 C50 1.275(3) . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 H1D 0.9800 . ? C2 C52 1.381(3) . ? C2 C3 1.395(3) . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.466(3) . ? C5 H5 0.9500 . ? C6 C7 1.504(3) . ? C7 C8 1.395(3) . ? C7 C12 1.403(3) . ? C8 C9 1.377(3) . ? C8 H8 0.9500 . ? C9 C10 1.370(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C13 C14 1.483(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.498(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.393(3) . ? C17 C22 1.406(3) . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C20 1.382(3) . ? C19 H19 0.9500 . ? C20 C21 1.381(3) . ? C20 H20 0.9500 . ? C21 C22 1.396(3) . ? C21 H21 0.9500 . ? C22 C23 1.503(3) . ? C24 C25 1.470(3) . ? C24 H24 0.9500 . ? C25 C26 1.381(3) . ? C26 C27 1.386(3) . ? C26 H26 0.9500 . ? C27 C29 1.383(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.397(3) . ? C29 H29 0.9500 . ? C30 C31 1.461(3) . ? C31 H31 0.9500 . ? C32 C33 1.497(4) . ? C33 C34 1.397(3) . ? C33 C38 1.401(3) . ? C34 C35 1.385(4) . ? C34 H34 0.9500 . ? C35 C36 1.368(4) . ? C35 H35 0.9500 . ? C36 C37 1.388(3) . ? C36 H36 0.9500 . ? C37 C38 1.397(3) . ? C37 H37 0.9500 . ? C39 C40 1.500(3) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.504(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.394(3) . ? C43 C48 1.404(3) . ? C44 C45 1.378(3) . ? C44 H44 0.9500 . ? C45 C46 1.380(4) . ? C45 H45 0.9500 . ? C46 C47 1.381(4) . ? C46 H46 0.9500 . ? C47 C48 1.391(3) . ? C47 H47 0.9500 . ? C48 C49 1.502(3) . ? C50 C51 1.472(3) . ? C50 H50 0.9500 . ? C51 C52 1.395(3) . ? C52 H52 0.9500 . ? O13 C53 1.308(4) . ? O13 H13 0.8400 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 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 C1 117.56(17) . . ? C12 O3 C13 119.58(16) . . ? C15 O4 C14 111.45(16) . . ? C17 O5 C16 116.66(16) . . ? C27 O7 C28 116.9(2) . . ? C38 O9 C39 118.46(17) . . ? C41 O10 C40 114.17(16) . . ? C43 O11 C42 118.79(16) . . ? C51 N1 C4 116.56(18) . . ? C5 N2 N3 113.80(18) . . ? C6 N3 N2 122.23(18) . . ? C6 N3 H3N 118.9 . . ? N2 N3 H3N 118.9 . . ? C23 N4 N5 116.98(17) . . ? C23 N4 H4N 121.5 . . ? N5 N4 H4N 121.5 . . ? C24 N5 N4 119.14(18) . . ? C30 N6 C25 116.96(19) . . ? C31 N7 N8 114.62(18) . . ? C32 N8 N7 119.22(19) . . ? C32 N8 H8N 120.4 . . ? N7 N8 H8N 120.4 . . ? C49 N9 N10 119.65(18) . . ? C49 N9 H9N 120.2 . . ? N10 N9 H9N 120.2 . . ? C50 N10 N9 115.74(18) . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C1 H1D 109.5 . . ? H1B C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? O1 C2 C52 124.8(2) . . ? O1 C2 C3 116.52(19) . . ? C52 C2 C3 118.66(19) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? N1 C4 C3 123.5(2) . . ? N1 C4 C5 113.98(19) . . ? C3 C4 C5 122.5(2) . . ? N2 C5 C4 123.7(2) . . ? N2 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? O2 C6 N3 122.6(2) . . ? O2 C6 C7 121.0(2) . . ? N3 C6 C7 116.39(19) . . ? C8 C7 C12 117.2(2) . . ? C8 C7 C6 116.0(2) . . ? C12 C7 C6 126.7(2) . . ? C9 C8 C7 121.9(2) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? O3 C12 C11 122.2(2) . . ? O3 C12 C7 117.31(19) . . ? C11 C12 C7 120.5(2) . . ? O3 C13 C14 106.02(18) . . ? O3 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? O3 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? O4 C14 C13 109.65(19) . . ? O4 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? O4 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O4 C15 C16 109.37(17) . . ? O4 C15 H15A 109.8 . . ? C16 C15 H15A 109.8 . . ? O4 C15 H15B 109.8 . . ? C16 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? O5 C16 C15 111.96(17) . . ? O5 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? O5 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? O5 C17 C18 121.26(18) . . ? O5 C17 C22 118.53(18) . . ? C18 C17 C22 120.2(2) . . ? C19 C18 C17 120.8(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 119.7(2) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 119.9(2) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 121.9(2) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C17 117.5(2) . . ? C21 C22 C23 115.23(18) . . ? C17 C22 C23 127.08(19) . . ? O6 C23 N4 122.04(19) . . ? O6 C23 C22 120.16(19) . . ? N4 C23 C22 117.71(17) . . ? N5 C24 C25 131.4(2) . . ? N5 C24 H24 114.3 . . ? C25 C24 H24 114.3 . . ? N6 C25 C26 122.9(2) . . ? N6 C25 C24 117.3(2) . . ? C26 C25 C24 119.8(2) . . ? C25 C26 C27 119.3(2) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? O7 C27 C29 124.5(2) . . ? O7 C27 C26 116.4(2) . . ? C29 C27 C26 119.1(2) . . ? O7 C28 H28A 109.5 . . ? O7 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O7 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 C30 117.6(2) . . ? C27 C29 H29 121.2 . . ? C30 C29 H29 121.2 . . ? N6 C30 C29 124.1(2) . . ? N6 C30 C31 113.44(19) . . ? C29 C30 C31 122.5(2) . . ? N7 C31 C30 121.4(2) . . ? N7 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? O8 C32 N8 122.2(2) . . ? O8 C32 C33 122.0(2) . . ? N8 C32 C33 115.8(2) . . ? C34 C33 C38 118.2(2) . . ? C34 C33 C32 115.6(2) . . ? C38 C33 C32 126.14(19) . . ? C35 C34 C33 121.3(3) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C36 C35 C34 119.8(2) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C37 120.8(2) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C36 C37 C38 119.6(3) . . ? C36 C37 H37 120.2 . . ? C38 C37 H37 120.2 . . ? O9 C38 C37 122.5(2) . . ? O9 C38 C33 117.19(19) . . ? C37 C38 C33 120.3(2) . . ? O9 C39 C40 107.98(17) . . ? O9 C39 H39A 110.1 . . ? C40 C39 H39A 110.1 . . ? O9 C39 H39B 110.1 . . ? C40 C39 H39B 110.1 . . ? H39A C39 H39B 108.4 . . ? O10 C40 C39 113.47(17) . . ? O10 C40 H40A 108.9 . . ? C39 C40 H40A 108.9 . . ? O10 C40 H40B 108.9 . . ? C39 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? O10 C41 C42 113.48(17) . . ? O10 C41 H41A 108.9 . . ? C42 C41 H41A 108.9 . . ? O10 C41 H41B 108.9 . . ? C42 C41 H41B 108.9 . . ? H41A C41 H41B 107.7 . . ? O11 C42 C41 106.81(16) . . ? O11 C42 H42A 110.4 . . ? C41 C42 H42A 110.4 . . ? O11 C42 H42B 110.4 . . ? C41 C42 H42B 110.4 . . ? H42A C42 H42B 108.6 . . ? O11 C43 C44 122.62(19) . . ? O11 C43 C48 116.98(18) . . ? C44 C43 C48 120.4(2) . . ? C45 C44 C43 119.9(2) . . ? C45 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C44 C45 C46 120.6(2) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C45 C46 C47 119.2(2) . . ? C45 C46 H46 120.4 . . ? C47 C46 H46 120.4 . . ? C46 C47 C48 122.0(2) . . ? C46 C47 H47 119.0 . . ? C48 C47 H47 119.0 . . ? C47 C48 C43 117.7(2) . . ? C47 C48 C49 115.4(2) . . ? C43 C48 C49 126.79(19) . . ? O12 C49 N9 122.5(2) . . ? O12 C49 C48 121.0(2) . . ? N9 C49 C48 116.41(18) . . ? N10 C50 C51 120.6(2) . . ? N10 C50 H50 119.7 . . ? C51 C50 H50 119.7 . . ? N1 C51 C52 124.1(2) . . ? N1 C51 C50 115.33(18) . . ? C52 C51 C50 120.6(2) . . ? C2 C52 C51 118.3(2) . . ? C2 C52 H52 120.9 . . ? C51 C52 H52 120.9 . . ? C53 O13 H13 109.5 . . ? O13 C53 H53A 109.5 . . ? O13 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? O13 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.486 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.048 # Attachment '- js1105.cif' data_js1105 _database_code_depnum_ccdc_archive 'CCDC 827939' #TrackingRef '- js1105.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N5 O6, C H4 O, H2 O' _chemical_formula_sum 'C27 H31 N5 O8' _chemical_formula_weight 553.57 _chemical_absolute_configuration ; 1866 Friedel pairs were averaged for the refinement ; 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 monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.0009(2) _cell_length_b 25.2757(5) _cell_length_c 12.9386(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.918(1) _cell_angle_gamma 90.00 _cell_volume 2613.16(10) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11217 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15099 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3118 _reflns_number_gt 2748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.8200P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(9) _refine_ls_number_reflns 3118 _refine_ls_number_parameters 372 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _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 O1 O -0.1732(2) 0.02999(7) 0.48699(13) 0.0349(4) Uani 1 1 d . . . O2 O -0.3203(3) -0.27698(7) 0.25111(14) 0.0429(5) Uani 1 1 d . . . O3 O 0.00504(19) -0.17218(6) 0.11384(11) 0.0254(3) Uani 1 1 d . . . O4 O 0.2982(2) -0.14429(7) 0.01807(13) 0.0322(4) Uani 1 1 d . . . O5 O 0.4102(2) -0.05095(6) -0.06903(13) 0.0339(4) Uani 1 1 d . . . O6 O 0.2437(3) 0.08851(7) 0.06196(16) 0.0445(5) Uani 1 1 d . . . N1 N -0.0514(2) -0.09799(8) 0.30489(14) 0.0261(4) Uani 1 1 d . . . N2 N -0.2160(3) -0.19858(8) 0.37585(15) 0.0310(4) Uani 1 1 d . . . N3 N -0.1881(3) -0.19827(7) 0.27141(14) 0.0269(4) Uani 1 1 d . . . H3N H -0.1363 -0.1717 0.2430 0.032 Uiso 1 1 calc R . . N4 N 0.2311(2) -0.00073(8) 0.06714(14) 0.0267(4) Uani 1 1 d . . . H4N H 0.2580 -0.0311 0.0391 0.032 Uiso 1 1 calc R . . N5 N 0.1388(2) 0.00036(8) 0.15384(14) 0.0269(4) Uani 1 1 d . . . C1 C -0.1358(4) 0.08253(10) 0.4550(2) 0.0414(6) Uani 1 1 d . . . H1A H -0.1776 0.1079 0.5049 0.062 Uiso 1 1 calc R . . H1B H -0.1896 0.0892 0.3865 0.062 Uiso 1 1 calc R . . H1C H -0.0143 0.0866 0.4517 0.062 Uiso 1 1 calc R . . C2 C -0.1266(3) -0.00998(9) 0.42549(17) 0.0274(5) Uani 1 1 d . . . C3 C -0.1666(3) -0.06076(10) 0.45727(17) 0.0277(5) Uani 1 1 d . . . H3 H -0.2175 -0.0664 0.5211 0.033 Uiso 1 1 calc R . . C4 C -0.1307(3) -0.10300(9) 0.39413(17) 0.0264(5) Uani 1 1 d . . . C5 C -0.1861(3) -0.15559(10) 0.42641(18) 0.0330(5) Uani 1 1 d . . . H5 H -0.2031 -0.1583 0.4983 0.040 Uiso 1 1 calc R . . C6 C -0.2433(3) -0.24045(9) 0.21400(17) 0.0273(5) Uani 1 1 d . . . C7 C -0.2080(3) -0.24016(9) 0.10100(17) 0.0255(5) Uani 1 1 d . . . C8 C -0.3028(3) -0.27444(9) 0.03737(18) 0.0299(5) Uani 1 1 d . . . H8 H -0.3873 -0.2953 0.0664 0.036 Uiso 1 1 calc R . . C9 C -0.2767(3) -0.27866(10) -0.06688(18) 0.0331(5) Uani 1 1 d . . . H9 H -0.3439 -0.3019 -0.1092 0.040 Uiso 1 1 calc R . . C10 C -0.1526(3) -0.24913(11) -0.10952(18) 0.0350(5) Uani 1 1 d . . . H10 H -0.1329 -0.2527 -0.1810 0.042 Uiso 1 1 calc R . . C11 C -0.0568(3) -0.21438(10) -0.04897(18) 0.0316(5) Uani 1 1 d . . . H11 H 0.0278 -0.1939 -0.0787 0.038 Uiso 1 1 calc R . . C12 C -0.0851(3) -0.20968(9) 0.05549(16) 0.0245(4) Uani 1 1 d . . . C13 C 0.1675(3) -0.18868(9) 0.15450(18) 0.0288(5) Uani 1 1 d . . . H13A H 0.1568 -0.2235 0.1887 0.035 Uiso 1 1 calc R . . H13B H 0.2084 -0.1630 0.2077 0.035 Uiso 1 1 calc R . . C14 C 0.2947(3) -0.19307(9) 0.0729(2) 0.0309(5) Uani 1 1 d . . . H14A H 0.4066 -0.2007 0.1057 0.037 Uiso 1 1 calc R . . H14B H 0.2639 -0.2223 0.0246 0.037 Uiso 1 1 calc R . . C15 C 0.4242(4) -0.14458(11) -0.0549(3) 0.0490(8) Uani 1 1 d . . . H15A H 0.4184 -0.1781 -0.0947 0.059 Uiso 1 1 calc R . . H15B H 0.5356 -0.1425 -0.0183 0.059 Uiso 1 1 calc R . . C16 C 0.4022(4) -0.09901(10) -0.1272(2) 0.0464(7) Uani 1 1 d . . . H16A H 0.4914 -0.0994 -0.1775 0.056 Uiso 1 1 calc R . . H16B H 0.2927 -0.1017 -0.1661 0.056 Uiso 1 1 calc R . . C17 C 0.4298(3) -0.00376(10) -0.11986(18) 0.0285(5) Uani 1 1 d . . . C18 C 0.5078(3) -0.00080(11) -0.21426(19) 0.0342(6) Uani 1 1 d . . . H18 H 0.5431 -0.0322 -0.2470 0.041 Uiso 1 1 calc R . . C19 C 0.5334(3) 0.04773(11) -0.2596(2) 0.0381(6) Uani 1 1 d . . . H19 H 0.5858 0.0496 -0.3238 0.046 Uiso 1 1 calc R . . C20 C 0.4831(3) 0.09389(11) -0.2122(2) 0.0394(6) Uani 1 1 d . . . H20 H 0.5018 0.1273 -0.2434 0.047 Uiso 1 1 calc R . . C21 C 0.4056(3) 0.09109(10) -0.1194(2) 0.0341(5) Uani 1 1 d . . . H21 H 0.3721 0.1228 -0.0871 0.041 Uiso 1 1 calc R . . C22 C 0.3753(3) 0.04249(9) -0.07180(18) 0.0286(5) Uani 1 1 d . . . C23 C 0.2803(3) 0.04566(9) 0.02519(19) 0.0289(5) Uani 1 1 d . . . C24 C 0.0886(3) -0.04479(9) 0.18418(17) 0.0264(5) Uani 1 1 d . . . H24 H 0.1125 -0.0757 0.1459 0.032 Uiso 1 1 calc R . . C25 C -0.0063(3) -0.04888(9) 0.27826(17) 0.0246(5) Uani 1 1 d . . . C26 C -0.0431(3) -0.00348(9) 0.33510(18) 0.0269(5) Uani 1 1 d . . . H26 H -0.0118 0.0307 0.3123 0.032 Uiso 1 1 calc R . . O27 O -0.3176(3) 0.11290(8) 0.18234(17) 0.0478(5) Uani 1 1 d . . . H27 H -0.207(5) 0.1168(14) 0.191(3) 0.057 Uiso 1 1 d . . . C27 C -0.4039(5) 0.16129(12) 0.1714(3) 0.0583(9) Uani 1 1 d . . . H27A H -0.4007 0.1797 0.2381 0.070 Uiso 1 1 calc R . . H27B H -0.5205 0.1545 0.1483 0.070 Uiso 1 1 calc R . . H27C H -0.3506 0.1833 0.1201 0.070 Uiso 1 1 calc R . . O1W O 0.0225(3) 0.12394(9) 0.21011(18) 0.0468(5) Uani 1 1 d . . . H1W H 0.083(5) 0.1077(14) 0.172(3) 0.056 Uiso 1 1 d . . . H2W H 0.071(5) 0.1536(15) 0.220(3) 0.056 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0399(10) 0.0326(9) 0.0325(9) -0.0102(7) 0.0047(7) 0.0024(8) O2 0.0576(12) 0.0369(10) 0.0360(9) -0.0067(8) 0.0195(8) -0.0189(9) O3 0.0258(8) 0.0251(8) 0.0254(7) -0.0014(6) 0.0031(6) -0.0021(6) O4 0.0300(9) 0.0288(8) 0.0390(9) 0.0010(7) 0.0139(7) 0.0011(7) O5 0.0433(10) 0.0276(8) 0.0315(8) 0.0005(7) 0.0100(8) -0.0016(7) O6 0.0530(12) 0.0260(9) 0.0565(12) -0.0022(8) 0.0231(10) -0.0019(8) N1 0.0274(10) 0.0274(10) 0.0238(9) -0.0023(7) 0.0049(8) -0.0003(8) N2 0.0401(12) 0.0295(10) 0.0243(9) -0.0004(8) 0.0113(8) -0.0034(9) N3 0.0341(10) 0.0242(9) 0.0230(8) 0.0004(7) 0.0086(7) -0.0030(8) N4 0.0280(10) 0.0259(9) 0.0267(9) -0.0002(8) 0.0054(8) -0.0010(8) N5 0.0245(10) 0.0287(10) 0.0278(10) -0.0010(8) 0.0040(8) -0.0006(8) C1 0.0521(17) 0.0279(13) 0.0438(15) -0.0091(11) -0.0016(12) 0.0045(12) C2 0.0246(11) 0.0311(11) 0.0261(10) -0.0069(9) -0.0016(9) 0.0023(9) C3 0.0260(11) 0.0353(12) 0.0219(10) -0.0036(9) 0.0019(9) -0.0014(9) C4 0.0273(12) 0.0300(11) 0.0218(10) -0.0027(9) 0.0008(9) -0.0006(9) C5 0.0407(14) 0.0358(13) 0.0233(10) -0.0016(10) 0.0098(10) -0.0016(11) C6 0.0293(12) 0.0250(11) 0.0281(11) -0.0027(9) 0.0075(9) -0.0021(9) C7 0.0252(11) 0.0245(11) 0.0269(11) 0.0000(8) 0.0027(9) 0.0014(9) C8 0.0275(12) 0.0298(12) 0.0327(12) -0.0016(9) 0.0030(9) -0.0034(9) C9 0.0307(12) 0.0380(14) 0.0304(12) -0.0074(10) -0.0014(10) -0.0030(10) C10 0.0396(13) 0.0447(14) 0.0209(10) -0.0050(10) 0.0041(10) -0.0030(11) C11 0.0326(13) 0.0363(13) 0.0263(11) 0.0004(10) 0.0060(9) -0.0041(10) C12 0.0254(11) 0.0241(11) 0.0241(10) -0.0010(8) 0.0012(8) -0.0003(9) C13 0.0326(13) 0.0275(11) 0.0261(11) 0.0011(9) -0.0018(9) -0.0017(9) C14 0.0304(12) 0.0263(12) 0.0363(12) -0.0004(9) 0.0042(10) -0.0003(10) C15 0.0486(17) 0.0324(14) 0.069(2) -0.0008(13) 0.0351(15) 0.0019(12) C16 0.065(2) 0.0360(15) 0.0412(15) -0.0083(11) 0.0289(14) -0.0111(13) C17 0.0235(12) 0.0333(13) 0.0285(11) 0.0038(9) -0.0004(9) -0.0025(9) C18 0.0278(13) 0.0454(15) 0.0295(12) 0.0022(10) 0.0023(10) -0.0001(10) C19 0.0304(14) 0.0552(17) 0.0286(12) 0.0123(11) 0.0014(10) -0.0047(12) C20 0.0313(13) 0.0420(15) 0.0446(15) 0.0175(12) 0.0011(11) -0.0046(11) C21 0.0284(12) 0.0313(13) 0.0427(14) 0.0087(11) 0.0019(11) 0.0001(10) C22 0.0216(11) 0.0319(12) 0.0320(12) 0.0055(10) -0.0001(9) -0.0032(9) C23 0.0227(12) 0.0302(12) 0.0338(12) 0.0003(10) 0.0019(9) -0.0032(9) C24 0.0274(12) 0.0258(11) 0.0261(11) -0.0030(9) 0.0019(9) -0.0009(9) C25 0.0219(11) 0.0266(11) 0.0254(10) -0.0018(9) 0.0011(8) -0.0012(9) C26 0.0250(12) 0.0260(11) 0.0295(11) -0.0034(9) 0.0003(9) -0.0015(9) O27 0.0480(13) 0.0395(11) 0.0568(12) 0.0019(9) 0.0114(10) -0.0002(9) C27 0.078(2) 0.0423(16) 0.0577(19) 0.0091(14) 0.0319(18) 0.0107(16) O1W 0.0451(12) 0.0403(11) 0.0565(12) -0.0122(9) 0.0181(10) -0.0104(9) _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 1.350(3) . ? O1 C1 1.427(3) . ? O2 C6 1.222(3) . ? O3 C12 1.391(3) . ? O3 C13 1.439(3) . ? O4 C15 1.416(3) . ? O4 C14 1.423(3) . ? O5 C17 1.375(3) . ? O5 C16 1.429(3) . ? O6 C23 1.224(3) . ? N1 C25 1.342(3) . ? N1 C4 1.351(3) . ? N2 C5 1.285(3) . ? N2 N3 1.381(2) . ? N3 C6 1.360(3) . ? N3 H3N 0.8800 . ? N4 C23 1.359(3) . ? N4 N5 1.374(2) . ? N4 H4N 0.8800 . ? N5 C24 1.278(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C26 1.386(3) . ? C2 C3 1.390(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.469(3) . ? C5 H5 0.9500 . ? C6 C7 1.503(3) . ? C7 C8 1.393(3) . ? C7 C12 1.402(3) . ? C8 C9 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.379(4) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C13 C14 1.507(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.488(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.402(3) . ? C17 C22 1.404(3) . ? C18 C19 1.380(4) . ? C18 H18 0.9500 . ? C19 C20 1.387(4) . ? C19 H19 0.9500 . ? C20 C21 1.382(4) . ? C20 H20 0.9500 . ? C21 C22 1.400(3) . ? C21 H21 0.9500 . ? C22 C23 1.502(3) . ? C24 C25 1.470(3) . ? C24 H24 0.9500 . ? C25 C26 1.402(3) . ? C26 H26 0.9500 . ? O27 C27 1.408(4) . ? O27 H27 0.89(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? O1W H1W 0.82(4) . ? O1W H2W 0.85(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 C2 O1 C1 117.18(19) . . ? C12 O3 C13 115.79(17) . . ? C15 O4 C14 111.14(19) . . ? C17 O5 C16 119.26(18) . . ? C25 N1 C4 116.74(19) . . ? C5 N2 N3 117.28(19) . . ? C6 N3 N2 117.75(17) . . ? C6 N3 H3N 121.1 . . ? N2 N3 H3N 121.1 . . ? C23 N4 N5 119.18(19) . . ? C23 N4 H4N 120.4 . . ? N5 N4 H4N 120.4 . . ? C24 N5 N4 115.04(18) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C26 124.6(2) . . ? O1 C2 C3 116.2(2) . . ? C26 C2 C3 119.1(2) . . ? C4 C3 C2 118.7(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? N1 C4 C3 123.6(2) . . ? N1 C4 C5 119.3(2) . . ? C3 C4 C5 117.1(2) . . ? N2 C5 C4 132.2(2) . . ? N2 C5 H5 113.9 . . ? C4 C5 H5 113.9 . . ? O2 C6 N3 122.3(2) . . ? O2 C6 C7 120.6(2) . . ? N3 C6 C7 117.09(18) . . ? C8 C7 C12 117.8(2) . . ? C8 C7 C6 116.63(19) . . ? C12 C7 C6 125.6(2) . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 O3 118.78(19) . . ? C11 C12 C7 121.0(2) . . ? O3 C12 C7 120.14(18) . . ? O3 C13 C14 113.24(18) . . ? O3 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? O3 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? O4 C14 C13 108.44(19) . . ? O4 C14 H14A 110.0 . . ? C13 C14 H14A 110.0 . . ? O4 C14 H14B 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? O4 C15 C16 110.5(2) . . ? O4 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O4 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? O5 C16 C15 109.1(2) . . ? O5 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? O5 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? O5 C17 C18 122.0(2) . . ? O5 C17 C22 117.70(19) . . ? C18 C17 C22 120.2(2) . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.5(2) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 119.6(2) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 121.5(2) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C17 118.1(2) . . ? C21 C22 C23 115.3(2) . . ? C17 C22 C23 126.6(2) . . ? O6 C23 N4 121.9(2) . . ? O6 C23 C22 120.9(2) . . ? N4 C23 C22 117.2(2) . . ? N5 C24 C25 120.0(2) . . ? N5 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? N1 C25 C26 123.7(2) . . ? N1 C25 C24 115.74(19) . . ? C26 C25 C24 120.5(2) . . ? C2 C26 C25 118.0(2) . . ? C2 C26 H26 121.0 . . ? C25 C26 H26 121.0 . . ? C27 O27 H27 113(2) . . ? O27 C27 H27A 109.5 . . ? O27 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O27 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? H1W O1W H2W 105(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.191 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.041