# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sachin1 #TrackingRef '12087_web_deposit_cif_file_0_SachinA.Pawar_1340366600.SACHIN1_final.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H53 N3 O13' _chemical_formula_weight 687.77 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9071(17) _cell_length_b 8.8430(14) _cell_length_c 19.865(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.897(3) _cell_angle_gamma 90.00 _cell_volume 1874.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11897 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 27.19 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9708 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11897 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.19 _reflns_number_total 4428 _reflns_number_gt 3201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0654P)^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 none _refine_ls_extinction_coef none _refine_ls_number_reflns 4428 _refine_ls_number_parameters 484 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.991 _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 0.46351(17) 0.1270(3) 0.74701(10) 0.0298(5) Uani 1 1 d . . . O2 O 0.47843(18) 0.1618(3) 0.63623(10) 0.0345(5) Uani 1 1 d . . . O3 O 0.68095(17) 0.1269(2) 0.78133(10) 0.0263(5) Uani 1 1 d . . . O4 O 0.80758(19) 0.2585(2) 0.67779(11) 0.0325(5) Uani 1 1 d . . . O5 O 1.1082(2) -0.0066(3) 0.75726(12) 0.0438(6) Uani 1 1 d . . . O6 O 1.2713(2) -0.1843(3) 0.91198(12) 0.0420(6) Uani 1 1 d . . . O7 O 1.6145(2) -0.4471(3) 0.82196(14) 0.0465(6) Uani 1 1 d . . . O8 O 1.6340(2) -0.1969(2) 0.82228(12) 0.0345(5) Uani 1 1 d . . . N1 N 0.8477(2) -0.1782(3) 0.77470(14) 0.0298(6) Uani 1 1 d D . . N2 N 1.1530(2) 0.0891(3) 0.86437(13) 0.0288(6) Uani 1 1 d D . . N3 N 1.4059(2) -0.1433(3) 0.84151(14) 0.0300(6) Uani 1 1 d D . . C1 C 0.3305(3) -0.0169(4) 0.6598(2) 0.0427(9) Uani 1 1 d . . . H1A H 0.2723 -0.0396 0.6900 0.064 Uiso 1 1 calc R . . H1B H 0.3954 -0.0952 0.6652 0.064 Uiso 1 1 calc R . . H1C H 0.2847 -0.0146 0.6119 0.064 Uiso 1 1 calc R . . C2 C 0.2958(3) 0.2621(4) 0.6722(2) 0.0428(9) Uani 1 1 d . . . H2A H 0.3400 0.3590 0.6803 0.064 Uiso 1 1 calc R . . H2B H 0.2432 0.2483 0.7062 0.064 Uiso 1 1 calc R . . H2C H 0.2431 0.2614 0.6259 0.064 Uiso 1 1 calc R . . C3 C 0.3906(3) 0.1344(4) 0.67881(15) 0.0283(7) Uani 1 1 d . . . C4 C 0.5761(3) 0.2135(3) 0.75127(15) 0.0260(7) Uani 1 1 d . . . H4 H 0.5727 0.3110 0.7764 0.031 Uiso 1 1 calc R . . C5 C 0.5833(3) 0.2402(4) 0.67558(16) 0.0286(7) Uani 1 1 d . . . H5 H 0.5843 0.3500 0.6635 0.034 Uiso 1 1 calc R . . C6 C 0.7028(3) 0.1576(3) 0.66760(15) 0.0270(7) Uani 1 1 d . . . H6 H 0.6914 0.1050 0.6222 0.032 Uiso 1 1 calc R . . C7 C 0.7198(3) 0.0453(3) 0.72667(14) 0.0246(6) Uani 1 1 d . . . H7 H 0.6614 -0.0416 0.7129 0.030 Uiso 1 1 calc R . . C8 C 0.8186(3) 0.3374(4) 0.61611(18) 0.0347(7) Uani 1 1 d . . . H8A H 0.8825 0.4179 0.6280 0.042 Uiso 1 1 calc R . . H8B H 0.7376 0.3867 0.5965 0.042 Uiso 1 1 calc R . . C9 C 0.8544(3) 0.2360(4) 0.56260(17) 0.0302(7) Uani 1 1 d . . . C10 C 0.9561(3) 0.1388(4) 0.57908(19) 0.0385(8) Uani 1 1 d . . . H10 H 1.0026 0.1344 0.6251 0.046 Uiso 1 1 calc R . . C11 C 0.9903(3) 0.0485(5) 0.5295(2) 0.0476(9) Uani 1 1 d . . . H11 H 1.0605 -0.0168 0.5414 0.057 Uiso 1 1 calc R . . C12 C 0.9227(4) 0.0525(5) 0.4620(2) 0.0501(10) Uani 1 1 d . . . H12 H 0.9457 -0.0103 0.4279 0.060 Uiso 1 1 calc R . . C13 C 0.8220(3) 0.1488(5) 0.44561(19) 0.0474(9) Uani 1 1 d . . . H13 H 0.7757 0.1537 0.3996 0.057 Uiso 1 1 calc R . . C14 C 0.7877(3) 0.2391(4) 0.49592(18) 0.0379(8) Uani 1 1 d . . . H14 H 0.7171 0.3039 0.4840 0.045 Uiso 1 1 calc R . . C15 C 0.8520(3) -0.0159(4) 0.75017(16) 0.0265(6) Uani 1 1 d . . . H15 H 0.8918 -0.0172 0.7091 0.032 Uiso 1 1 calc R . . C16 C 0.8569(3) -0.2954(4) 0.72139(19) 0.0409(8) Uani 1 1 d . . . H16A H 0.8530 -0.3967 0.7421 0.049 Uiso 1 1 calc R . . H16B H 0.9398 -0.2860 0.7088 0.049 Uiso 1 1 calc R . . C17 C 0.7571(3) -0.2861(3) 0.65688(17) 0.0356(8) Uani 1 1 d . . . C18 C 0.6371(3) -0.3398(4) 0.65610(17) 0.0378(8) Uani 1 1 d . . . H18 H 0.6163 -0.3757 0.6974 0.045 Uiso 1 1 calc R . . C19 C 0.5479(4) -0.3410(5) 0.59557(19) 0.0506(10) Uani 1 1 d . . . H19 H 0.4663 -0.3788 0.5955 0.061 Uiso 1 1 calc R . . C20 C 0.5756(5) -0.2888(6) 0.5361(2) 0.0670(13) Uani 1 1 d . . . H20 H 0.5135 -0.2897 0.4948 0.080 Uiso 1 1 calc R . . C21 C 0.6936(6) -0.2348(6) 0.5358(2) 0.0729(15) Uani 1 1 d . . . H21 H 0.7132 -0.1986 0.4942 0.087 Uiso 1 1 calc R . . C22 C 0.7840(4) -0.2332(4) 0.5961(2) 0.0537(11) Uani 1 1 d . . . H22 H 0.8653 -0.1954 0.5957 0.064 Uiso 1 1 calc R . . C23 C 0.9353(3) 0.0781(4) 0.80516(16) 0.0295(7) Uani 1 1 d . . . H23A H 0.9165 0.0536 0.8506 0.035 Uiso 1 1 calc R . . H23B H 0.9172 0.1867 0.7960 0.035 Uiso 1 1 calc R . . C24 C 1.0733(3) 0.0482(4) 0.80692(16) 0.0289(7) Uani 1 1 d . . . C25 C 1.2885(3) 0.0708(4) 0.87087(15) 0.0278(7) Uani 1 1 d . . . H25 H 1.3118 0.1109 0.8281 0.033 Uiso 1 1 calc R . . C26 C 1.3586(3) 0.1632(4) 0.93238(17) 0.0374(8) Uani 1 1 d . . . H26 H 1.3298 0.1308 0.9748 0.045 Uiso 1 1 calc R . . C27 C 1.3292(4) 0.3305(5) 0.9197(3) 0.0678(13) Uani 1 1 d . . . H27A H 1.3675 0.3665 0.8822 0.102 Uiso 1 1 calc R . . H27B H 1.3630 0.3879 0.9616 0.102 Uiso 1 1 calc R . . H27C H 1.2383 0.3446 0.9072 0.102 Uiso 1 1 calc R . . C28 C 1.4992(3) 0.1408(7) 0.9433(2) 0.0639(13) Uani 1 1 d . . . H28A H 1.5411 0.2015 0.9827 0.096 Uiso 1 1 calc R . . H28B H 1.5282 0.1727 0.9020 0.096 Uiso 1 1 calc R . . H28C H 1.5193 0.0337 0.9524 0.096 Uiso 1 1 calc R . . C29 C 1.3205(3) -0.0966(4) 0.87662(16) 0.0304(7) Uani 1 1 d . . . C30 C 1.4403(3) -0.3026(4) 0.83898(17) 0.0330(7) Uani 1 1 d . . . H30 H 1.4365 -0.3504 0.8841 0.040 Uiso 1 1 calc R . . C31 C 1.3490(3) -0.3852(5) 0.7822(2) 0.0550(11) Uani 1 1 d . . . H31A H 1.3549 -0.3429 0.7374 0.082 Uiso 1 1 calc R . . H31B H 1.2634 -0.3726 0.7895 0.082 Uiso 1 1 calc R . . H31C H 1.3701 -0.4930 0.7834 0.082 Uiso 1 1 calc R . . C32 C 1.5747(3) -0.3171(4) 0.82724(16) 0.0315(7) Uani 1 1 d . . . O1W O 1.0436(3) -0.3288(4) 0.85217(16) 0.0703(9) Uani 1 1 d D . . O2W O 0.7858(3) -0.0461(3) 0.93458(15) 0.0530(7) Uani 1 1 d D . . O3W O 0.8325(2) 0.2430(3) 0.97476(14) 0.0441(6) Uani 1 1 d D . . O4W O 1.0883(2) 0.1966(3) 0.99510(13) 0.0465(6) Uani 1 1 d D . . O5W O 0.8540(3) 0.4919(3) 0.89388(17) 0.0606(8) Uani 1 1 d D . . H1X H 0.914(3) -0.197(5) 0.8161(13) 0.067(13) Uiso 1 1 d D . . H1Y H 0.775(2) -0.203(5) 0.793(2) 0.063(13) Uiso 1 1 d D . . H2 H 1.121(3) 0.105(4) 0.9054(10) 0.035(9) Uiso 1 1 d D . . H3 H 1.447(3) -0.073(3) 0.8164(16) 0.046(10) Uiso 1 1 d D . . H1W1 H 1.107(3) -0.294(6) 0.8787(18) 0.090 Uiso 1 1 d D . . H1W2 H 1.013(4) -0.389(5) 0.8767(19) 0.090 Uiso 1 1 d D . . H2W1 H 0.723(3) -0.075(5) 0.906(2) 0.090 Uiso 1 1 d D . . H2W2 H 0.821(4) -0.125(3) 0.952(2) 0.090 Uiso 1 1 d D . . H3W1 H 0.801(4) 0.261(5) 1.0086(17) 0.090 Uiso 1 1 d D . . H3W2 H 0.803(4) 0.159(3) 0.961(2) 0.090 Uiso 1 1 d D . . H4W1 H 1.0107(13) 0.210(6) 0.986(2) 0.090 Uiso 1 1 d D . . H4W2 H 1.098(4) 0.128(4) 1.024(2) 0.090 Uiso 1 1 d D . . H5W1 H 0.840(4) 0.413(4) 0.915(2) 0.090 Uiso 1 1 d D . . H5W2 H 0.784(2) 0.510(5) 0.869(2) 0.090 Uiso 1 1 d 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 0.0236(10) 0.0405(12) 0.0260(11) 0.0025(10) 0.0067(9) -0.0036(10) O2 0.0253(10) 0.0541(14) 0.0239(11) 0.0013(11) 0.0048(9) -0.0025(11) O3 0.0237(10) 0.0300(11) 0.0262(10) -0.0035(9) 0.0070(8) 0.0013(9) O4 0.0298(11) 0.0348(12) 0.0359(12) -0.0018(10) 0.0135(9) -0.0103(10) O5 0.0241(11) 0.0738(18) 0.0348(13) -0.0158(13) 0.0087(10) -0.0008(11) O6 0.0353(13) 0.0484(14) 0.0472(15) 0.0126(13) 0.0198(11) 0.0001(12) O7 0.0505(15) 0.0271(12) 0.0649(17) -0.0050(12) 0.0192(13) 0.0046(11) O8 0.0310(11) 0.0290(11) 0.0466(14) -0.0014(10) 0.0150(10) -0.0003(10) N1 0.0256(13) 0.0282(14) 0.0357(15) -0.0002(12) 0.0069(12) 0.0024(12) N2 0.0167(11) 0.0403(15) 0.0296(14) -0.0046(12) 0.0054(11) 0.0017(11) N3 0.0263(13) 0.0277(13) 0.0389(15) 0.0044(12) 0.0134(12) 0.0022(11) C1 0.0361(19) 0.043(2) 0.050(2) -0.0147(18) 0.0119(17) -0.0039(16) C2 0.0354(18) 0.045(2) 0.048(2) 0.0024(18) 0.0070(16) 0.0112(16) C3 0.0238(14) 0.0342(17) 0.0275(16) 0.0006(14) 0.0068(12) 0.0015(13) C4 0.0205(14) 0.0233(15) 0.0344(17) -0.0020(13) 0.0059(12) 0.0003(12) C5 0.0255(15) 0.0265(14) 0.0349(17) 0.0045(14) 0.0087(13) 0.0012(13) C6 0.0233(14) 0.0279(16) 0.0309(16) -0.0041(13) 0.0084(12) -0.0042(13) C7 0.0233(14) 0.0264(15) 0.0246(15) -0.0034(13) 0.0060(12) -0.0010(12) C8 0.0394(18) 0.0256(16) 0.045(2) 0.0022(15) 0.0218(15) -0.0026(14) C9 0.0292(16) 0.0271(15) 0.0387(18) 0.0039(14) 0.0174(14) -0.0035(13) C10 0.0278(16) 0.042(2) 0.047(2) 0.0018(17) 0.0118(14) 0.0039(15) C11 0.0318(18) 0.050(2) 0.064(2) -0.004(2) 0.0160(18) 0.0101(17) C12 0.048(2) 0.049(2) 0.059(2) -0.014(2) 0.026(2) 0.0007(19) C13 0.046(2) 0.056(2) 0.041(2) -0.0021(19) 0.0108(16) -0.003(2) C14 0.0334(17) 0.0389(17) 0.044(2) 0.0071(17) 0.0154(16) 0.0068(15) C15 0.0232(14) 0.0279(15) 0.0297(16) -0.0015(13) 0.0083(12) -0.0011(12) C16 0.0410(18) 0.0307(18) 0.053(2) -0.0091(16) 0.0138(16) 0.0080(15) C17 0.0445(19) 0.0245(16) 0.0394(19) -0.0082(14) 0.0123(16) 0.0036(14) C18 0.0436(18) 0.0349(18) 0.0371(18) -0.0074(16) 0.0133(15) 0.0008(16) C19 0.048(2) 0.057(2) 0.044(2) -0.010(2) 0.0039(17) 0.003(2) C20 0.080(3) 0.081(3) 0.034(2) -0.006(2) 0.000(2) 0.003(3) C21 0.114(4) 0.076(3) 0.033(2) 0.003(2) 0.024(3) 0.000(3) C22 0.075(3) 0.043(2) 0.051(2) -0.0048(19) 0.032(2) -0.007(2) C23 0.0207(14) 0.0374(17) 0.0304(16) -0.0056(14) 0.0051(12) 0.0011(13) C24 0.0241(15) 0.0354(16) 0.0291(16) 0.0005(14) 0.0096(13) 0.0023(13) C25 0.0185(14) 0.0379(17) 0.0272(15) 0.0010(14) 0.0053(12) -0.0006(13) C26 0.0284(15) 0.050(2) 0.0341(18) -0.0062(17) 0.0063(14) -0.0077(16) C27 0.068(3) 0.054(3) 0.083(3) -0.020(3) 0.021(2) -0.019(2) C28 0.0296(18) 0.102(4) 0.056(2) -0.022(3) -0.0004(17) -0.008(2) C29 0.0198(14) 0.0418(18) 0.0283(16) 0.0023(15) 0.0023(13) -0.0002(14) C30 0.0342(16) 0.0283(17) 0.0380(18) 0.0028(14) 0.0112(14) -0.0034(14) C31 0.041(2) 0.045(2) 0.073(3) -0.006(2) 0.0008(19) -0.0115(18) C32 0.0352(16) 0.0279(16) 0.0317(17) -0.0010(14) 0.0079(14) 0.0028(14) O1W 0.0463(17) 0.080(2) 0.081(2) 0.027(2) 0.0041(15) -0.0070(16) O2W 0.0581(18) 0.0422(14) 0.0536(18) 0.0002(13) -0.0005(14) 0.0000(13) O3W 0.0431(15) 0.0426(14) 0.0511(16) -0.0028(13) 0.0201(12) 0.0013(12) O4W 0.0411(13) 0.0543(17) 0.0470(15) -0.0061(13) 0.0163(12) 0.0006(12) O5W 0.0549(17) 0.0463(16) 0.078(2) 0.0145(16) 0.0074(15) -0.0009(14) _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 C3 1.424(3) . ? O1 C4 1.434(3) . ? O2 C3 1.423(4) . ? O2 C5 1.426(4) . ? O3 C4 1.404(3) . ? O3 C7 1.438(3) . ? O4 C6 1.431(3) . ? O4 C8 1.437(4) . ? O5 C24 1.228(4) . ? O6 C29 1.239(4) . ? O7 C32 1.241(4) . ? O8 C32 1.259(4) . ? N1 C16 1.500(4) . ? N1 C15 1.520(4) . ? N1 H1X 0.989(10) . ? N1 H1Y 0.971(10) . ? N2 C24 1.334(4) . ? N2 C25 1.466(4) . ? N2 H2 0.963(10) . ? N3 C29 1.339(4) . ? N3 C30 1.461(4) . ? N3 H3 0.965(10) . ? C1 C3 1.503(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.518(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.540(4) . ? C4 H4 1.0000 . ? C5 C6 1.530(4) . ? C5 H5 1.0000 . ? C6 C7 1.519(4) . ? C6 H6 1.0000 . ? C7 C15 1.520(4) . ? C7 H7 1.0000 . ? C8 C9 1.502(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.374(5) . ? C9 C10 1.388(5) . ? C10 C11 1.378(5) . ? C10 H10 0.9500 . ? C11 C12 1.390(6) . ? C11 H11 0.9500 . ? C12 C13 1.375(5) . ? C12 H12 0.9500 . ? C13 C14 1.390(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C23 1.517(4) . ? C15 H15 1.0000 . ? C16 C17 1.503(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.381(5) . ? C17 C18 1.389(5) . ? C18 C19 1.382(5) . ? C18 H18 0.9500 . ? C19 C20 1.360(6) . ? C19 H19 0.9500 . ? C20 C21 1.374(7) . ? C20 H20 0.9500 . ? C21 C22 1.386(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.521(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C25 C29 1.520(5) . ? C25 C26 1.537(4) . ? C25 H25 1.0000 . ? C26 C28 1.517(5) . ? C26 C27 1.523(6) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C30 C31 1.528(5) . ? C30 C32 1.536(4) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? O1W H1W1 0.838(10) . ? O1W H1W2 0.840(10) . ? O2W H2W1 0.830(10) . ? O2W H2W2 0.831(10) . ? O3W H3W1 0.834(10) . ? O3W H3W2 0.835(10) . ? O4W H4W1 0.837(10) . ? O4W H4W2 0.836(10) . ? O5W H5W1 0.842(10) . ? O5W H5W2 0.840(10) . ? 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 C3 O1 C4 109.6(2) . . ? C3 O2 C5 108.6(2) . . ? C4 O3 C7 107.1(2) . . ? C6 O4 C8 112.8(2) . . ? C16 N1 C15 114.6(3) . . ? C16 N1 H1X 109(3) . . ? C15 N1 H1X 111(3) . . ? C16 N1 H1Y 107(3) . . ? C15 N1 H1Y 115(3) . . ? H1X N1 H1Y 99(3) . . ? C24 N2 C25 120.8(2) . . ? C24 N2 H2 119(2) . . ? C25 N2 H2 118.6(19) . . ? C29 N3 C30 121.8(3) . . ? C29 N3 H3 121(2) . . ? C30 N3 H3 117(2) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O2 C3 O1 105.1(2) . . ? O2 C3 C1 108.3(3) . . ? O1 C3 C1 109.1(3) . . ? O2 C3 C2 110.6(3) . . ? O1 C3 C2 110.7(3) . . ? C1 C3 C2 112.7(3) . . ? O3 C4 O1 110.3(2) . . ? O3 C4 C5 107.3(2) . . ? O1 C4 C5 103.9(2) . . ? O3 C4 H4 111.7 . . ? O1 C4 H4 111.7 . . ? C5 C4 H4 111.7 . . ? O2 C5 C6 108.4(2) . . ? O2 C5 C4 105.3(2) . . ? C6 C5 C4 104.1(2) . . ? O2 C5 H5 112.8 . . ? C6 C5 H5 112.8 . . ? C4 C5 H5 112.8 . . ? O4 C6 C7 109.4(2) . . ? O4 C6 C5 111.1(3) . . ? C7 C6 C5 101.7(2) . . ? O4 C6 H6 111.4 . . ? C7 C6 H6 111.4 . . ? C5 C6 H6 111.4 . . ? O3 C7 C6 104.3(2) . . ? O3 C7 C15 110.8(2) . . ? C6 C7 C15 115.3(2) . . ? O3 C7 H7 108.7 . . ? C6 C7 H7 108.7 . . ? C15 C7 H7 108.7 . . ? O4 C8 C9 113.2(3) . . ? O4 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? O4 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 118.6(3) . . ? C14 C9 C8 120.5(3) . . ? C10 C9 C8 121.0(3) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 118.9(4) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C14 C13 121.0(3) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C23 C15 C7 114.6(3) . . ? C23 C15 N1 109.8(3) . . ? C7 C15 N1 110.2(2) . . ? C23 C15 H15 107.3 . . ? C7 C15 H15 107.3 . . ? N1 C15 H15 107.3 . . ? N1 C16 C17 115.0(3) . . ? N1 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? N1 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C22 C17 C18 118.4(3) . . ? C22 C17 C16 121.1(3) . . ? C18 C17 C16 120.4(3) . . ? C19 C18 C17 120.3(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 120.7(4) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.9(4) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 120.8(4) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C15 C23 C24 111.4(3) . . ? C15 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C15 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? O5 C24 N2 122.6(3) . . ? O5 C24 C23 121.3(3) . . ? N2 C24 C23 116.1(3) . . ? N2 C25 C29 109.0(3) . . ? N2 C25 C26 109.8(2) . . ? C29 C25 C26 112.9(3) . . ? N2 C25 H25 108.3 . . ? C29 C25 H25 108.3 . . ? C26 C25 H25 108.3 . . ? C28 C26 C27 108.8(4) . . ? C28 C26 C25 111.6(3) . . ? C27 C26 C25 109.4(3) . . ? C28 C26 H26 109.0 . . ? C27 C26 H26 109.0 . . ? C25 C26 H26 109.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O6 C29 N3 122.1(3) . . ? O6 C29 C25 122.2(3) . . ? N3 C29 C25 115.8(3) . . ? N3 C30 C31 110.7(3) . . ? N3 C30 C32 110.2(3) . . ? C31 C30 C32 110.2(3) . . ? N3 C30 H30 108.6 . . ? C31 C30 H30 108.6 . . ? C32 C30 H30 108.6 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O7 C32 O8 125.5(3) . . ? O7 C32 C30 116.9(3) . . ? O8 C32 C30 117.6(3) . . ? H1W1 O1W H1W2 104.4(17) . . ? H2W1 O2W H2W2 105.5(17) . . ? H3W1 O3W H3W2 104.5(17) . . ? H4W1 O4W H4W2 103.8(17) . . ? H5W1 O5W H5W2 102.9(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 C5 O2 C3 O1 -27.6(3) . . . . ? C5 O2 C3 C1 -144.2(3) . . . . ? C5 O2 C3 C2 91.8(3) . . . . ? C4 O1 C3 O2 26.2(3) . . . . ? C4 O1 C3 C1 142.2(2) . . . . ? C4 O1 C3 C2 -93.2(3) . . . . ? C7 O3 C4 O1 88.0(3) . . . . ? C7 O3 C4 C5 -24.5(3) . . . . ? C3 O1 C4 O3 -129.3(2) . . . . ? C3 O1 C4 C5 -14.6(3) . . . . ? C3 O2 C5 C6 129.5(3) . . . . ? C3 O2 C5 C4 18.5(3) . . . . ? O3 C4 C5 O2 114.4(2) . . . . ? O1 C4 C5 O2 -2.4(3) . . . . ? O3 C4 C5 C6 0.4(3) . . . . ? O1 C4 C5 C6 -116.3(2) . . . . ? C8 O4 C6 C7 162.5(2) . . . . ? C8 O4 C6 C5 -86.0(3) . . . . ? O2 C5 C6 O4 153.9(2) . . . . ? C4 C5 C6 O4 -94.4(3) . . . . ? O2 C5 C6 C7 -89.9(3) . . . . ? C4 C5 C6 C7 21.9(3) . . . . ? C4 O3 C7 C6 39.2(3) . . . . ? C4 O3 C7 C15 163.9(2) . . . . ? O4 C6 C7 O3 80.5(3) . . . . ? C5 C6 C7 O3 -37.0(3) . . . . ? O4 C6 C7 C15 -41.2(3) . . . . ? C5 C6 C7 C15 -158.7(2) . . . . ? C6 O4 C8 C9 -68.7(3) . . . . ? O4 C8 C9 C14 130.2(3) . . . . ? O4 C8 C9 C10 -50.5(4) . . . . ? C14 C9 C10 C11 0.7(5) . . . . ? C8 C9 C10 C11 -178.5(3) . . . . ? C9 C10 C11 C12 -0.5(6) . . . . ? C10 C11 C12 C13 0.6(6) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C10 C9 C14 C13 -1.0(5) . . . . ? C8 C9 C14 C13 178.2(3) . . . . ? C12 C13 C14 C9 1.1(6) . . . . ? O3 C7 C15 C23 -29.5(3) . . . . ? C6 C7 C15 C23 88.6(3) . . . . ? O3 C7 C15 N1 94.9(3) . . . . ? C6 C7 C15 N1 -146.9(3) . . . . ? C16 N1 C15 C23 -137.3(3) . . . . ? C16 N1 C15 C7 95.6(3) . . . . ? C15 N1 C16 C17 -58.1(4) . . . . ? N1 C16 C17 C22 106.6(4) . . . . ? N1 C16 C17 C18 -77.5(4) . . . . ? C22 C17 C18 C19 0.6(5) . . . . ? C16 C17 C18 C19 -175.4(3) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? C18 C19 C20 C21 0.3(7) . . . . ? C19 C20 C21 C22 -0.2(8) . . . . ? C18 C17 C22 C21 -0.5(6) . . . . ? C16 C17 C22 C21 175.5(4) . . . . ? C20 C21 C22 C17 0.3(7) . . . . ? C7 C15 C23 C24 -158.5(3) . . . . ? N1 C15 C23 C24 76.8(3) . . . . ? C25 N2 C24 O5 0.3(5) . . . . ? C25 N2 C24 C23 -177.8(3) . . . . ? C15 C23 C24 O5 20.6(5) . . . . ? C15 C23 C24 N2 -161.3(3) . . . . ? C24 N2 C25 C29 -70.8(4) . . . . ? C24 N2 C25 C26 165.1(3) . . . . ? N2 C25 C26 C28 176.9(3) . . . . ? C29 C25 C26 C28 55.0(4) . . . . ? N2 C25 C26 C27 -62.6(4) . . . . ? C29 C25 C26 C27 175.5(3) . . . . ? C30 N3 C29 O6 4.2(5) . . . . ? C30 N3 C29 C25 -176.3(3) . . . . ? N2 C25 C29 O6 -41.4(4) . . . . ? C26 C25 C29 O6 80.9(4) . . . . ? N2 C25 C29 N3 139.1(3) . . . . ? C26 C25 C29 N3 -98.5(3) . . . . ? C29 N3 C30 C31 84.8(4) . . . . ? C29 N3 C30 C32 -153.0(3) . . . . ? N3 C30 C32 O7 -177.9(3) . . . . ? C31 C30 C32 O7 -55.4(4) . . . . ? N3 C30 C32 O8 0.6(4) . . . . ? C31 C30 C32 O8 123.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.19 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.415 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 888183' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H48 N3 O10' _chemical_formula_sum 'C32 H49 N3 O10' _chemical_formula_weight 635.74 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 41.043(8) _cell_length_b 5.0993(10) _cell_length_c 16.334(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3418.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 30457 _cell_measurement_theta_min 0.99 _cell_measurement_theta_max 25.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9678 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _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 'Bruker Smart ApexII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30547 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 0.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5098 _reflns_number_gt 4923 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT-plus (Bruker, 2009)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1038P)^2^+12.9862P] 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 0.0046(9) _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 0.2(16) _refine_ls_number_reflns 5098 _refine_ls_number_parameters 416 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1699 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.003 _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 0.18279(10) 1.0636(12) -0.3622(2) 0.0273(11) Uani 1 1 d . . . C2 C 0.18775(12) 1.1630(12) -0.4420(3) 0.0324(12) Uani 1 1 d . . . H2 H 0.1746 1.1006 -0.4857 0.039 Uiso 1 1 calc R . . C3 C 0.21070(13) 1.3438(14) -0.4572(3) 0.0420(15) Uani 1 1 d . . . H3 H 0.2145 1.3968 -0.5121 0.050 Uiso 1 1 calc R . . C4 C 0.22919(12) 1.4567(13) -0.3945(3) 0.0426(15) Uani 1 1 d . . . H4 H 0.2444 1.5929 -0.4052 0.051 Uiso 1 1 calc R . . C5 C 0.22420(11) 1.3588(14) -0.3144(3) 0.0403(14) Uani 1 1 d . . . H5 H 0.2371 1.4233 -0.2706 0.048 Uiso 1 1 calc R . . C6 C 0.20134(10) 1.1752(12) -0.2994(3) 0.0302(12) Uani 1 1 d . . . H6 H 0.1977 1.1201 -0.2446 0.036 Uiso 1 1 calc R . . C7 C 0.15834(10) 0.8524(11) -0.3463(2) 0.0250(10) Uani 1 1 d . . . H7A H 0.1411 0.8572 -0.3886 0.030 Uiso 1 1 calc R . . H7B H 0.1690 0.6785 -0.3485 0.030 Uiso 1 1 calc R . . C8 C 0.12299(9) 0.6854(10) -0.2420(2) 0.0196(9) Uani 1 1 d . . . H8 H 0.1311 0.5083 -0.2586 0.024 Uiso 1 1 calc R . . C9 C 0.08919(10) 0.7437(10) -0.2750(3) 0.0235(10) Uani 1 1 d . . . H9 H 0.0899 0.8048 -0.3332 0.028 Uiso 1 1 calc R . . C10 C 0.03747(10) 0.6252(10) -0.2270(3) 0.0242(10) Uani 1 1 d . . . C11 C 0.01002(11) 0.5803(12) -0.2861(3) 0.0340(12) Uani 1 1 d . . . H11A H -0.0105 0.6409 -0.2618 0.051 Uiso 1 1 calc R . . H11B H 0.0084 0.3927 -0.2986 0.051 Uiso 1 1 calc R . . H11C H 0.0142 0.6779 -0.3367 0.051 Uiso 1 1 calc R . . C12 C 0.03178(11) 0.4845(13) -0.1453(3) 0.0335(12) Uani 1 1 d . . . H12A H 0.0503 0.5168 -0.1088 0.050 Uiso 1 1 calc R . . H12B H 0.0296 0.2957 -0.1550 0.050 Uiso 1 1 calc R . . H12C H 0.0118 0.5512 -0.1199 0.050 Uiso 1 1 calc R . . C13 C 0.07594(10) 0.9533(12) -0.2181(3) 0.0301(12) Uani 1 1 d . . . H13 H 0.0807 1.1347 -0.2381 0.036 Uiso 1 1 calc R . . C14 C 0.11676(10) 0.7065(11) -0.1491(2) 0.0220(10) Uani 1 1 d . . . H14 H 0.1093 0.5336 -0.1272 0.026 Uiso 1 1 calc R . . C15 C 0.14533(9) 0.8087(10) -0.0982(2) 0.0170(9) Uani 1 1 d . . . H15 H 0.1496 0.9950 -0.1140 0.020 Uiso 1 1 calc R . . C16 C 0.17681(9) 0.6518(9) -0.1098(2) 0.0191(9) Uani 1 1 d . . . H16A H 0.1765 0.4955 -0.0738 0.023 Uiso 1 1 calc R . . H16B H 0.1784 0.5912 -0.1672 0.023 Uiso 1 1 calc R . . C17 C 0.20624(9) 0.8221(9) -0.0890(2) 0.0175(9) Uani 1 1 d . . . C18 C 0.26342(10) 0.8578(11) -0.0951(3) 0.0257(10) Uani 1 1 d . . . H18A H 0.2672 0.8734 -0.0354 0.031 Uiso 1 1 calc R . . H18B H 0.2613 1.0360 -0.1186 0.031 Uiso 1 1 calc R . . C19 C 0.29143(11) 0.7096(14) -0.1358(3) 0.0413(14) Uani 1 1 d . . . H19A H 0.2950 0.5431 -0.1072 0.062 Uiso 1 1 calc R . . H19B H 0.3113 0.8159 -0.1331 0.062 Uiso 1 1 calc R . . H19C H 0.2860 0.6747 -0.1932 0.062 Uiso 1 1 calc R . . C20 C 0.12462(9) 1.0220(9) 0.0280(2) 0.0165(9) Uani 1 1 d . . . C21 C 0.10700(9) 0.9553(10) 0.1092(2) 0.0197(10) Uani 1 1 d . . . H21 H 0.1013 0.7647 0.1093 0.024 Uiso 1 1 calc R . . C22 C 0.07518(10) 1.1195(12) 0.1152(2) 0.0298(12) Uani 1 1 d . . . H22 H 0.0801 1.3101 0.1078 0.036 Uiso 1 1 calc R . . C23 C 0.05196(11) 1.0228(16) 0.0475(3) 0.0459(17) Uani 1 1 d . . . H23A H 0.0397 0.8704 0.0673 0.069 Uiso 1 1 calc R . . H23B H 0.0646 0.9732 -0.0009 0.069 Uiso 1 1 calc R . . H23C H 0.0367 1.1635 0.0330 0.069 Uiso 1 1 calc R . . C24 C 0.05933(12) 1.0711(19) 0.1997(3) 0.060(2) Uani 1 1 d . . . H24A H 0.0361 1.1133 0.1969 0.090 Uiso 1 1 calc R . . H24B H 0.0698 1.1827 0.2408 0.090 Uiso 1 1 calc R . . H24C H 0.0620 0.8865 0.2150 0.090 Uiso 1 1 calc R . . C25 C 0.14089(9) 0.8121(9) 0.2220(2) 0.0154(8) Uani 1 1 d . . . C26 C 0.15757(9) 0.8900(11) 0.3023(2) 0.0232(10) Uani 1 1 d . . . H26 H 0.1645 1.0777 0.2992 0.028 Uiso 1 1 calc R . . C27 C 0.18695(10) 0.7190(11) 0.3196(3) 0.0268(11) Uani 1 1 d . . . H27A H 0.1974 0.7772 0.3704 0.040 Uiso 1 1 calc R . . H27B H 0.2025 0.7329 0.2742 0.040 Uiso 1 1 calc R . . H27C H 0.1800 0.5362 0.3255 0.040 Uiso 1 1 calc R . . C28 C 0.11583(10) 1.0667(10) 0.3957(2) 0.0195(9) Uani 1 1 d . . . C29 C 0.06959(10) 1.1731(10) 0.4836(2) 0.0202(10) Uani 1 1 d . . . C30 C 0.08903(11) 1.3383(12) 0.5444(2) 0.0304(12) Uani 1 1 d . . . H30A H 0.1013 1.2225 0.5811 0.046 Uiso 1 1 calc R . . H30B H 0.0741 1.4468 0.5766 0.046 Uiso 1 1 calc R . . H30C H 0.1042 1.4516 0.5145 0.046 Uiso 1 1 calc R . . C31 C 0.04498(10) 1.0008(11) 0.5286(3) 0.0266(10) Uani 1 1 d . . . H31A H 0.0312 0.9101 0.4887 0.040 Uiso 1 1 calc R . . H31B H 0.0314 1.1104 0.5641 0.040 Uiso 1 1 calc R . . H31C H 0.0566 0.8713 0.5619 0.040 Uiso 1 1 calc R . . C32 C 0.05194(11) 1.3425(12) 0.4200(2) 0.0310(12) Uani 1 1 d . . . H32A H 0.0677 1.4572 0.3927 0.047 Uiso 1 1 calc R . . H32B H 0.0354 1.4497 0.4474 0.047 Uiso 1 1 calc R . . H32C H 0.0415 1.2291 0.3794 0.047 Uiso 1 1 calc R . . N1 N 0.13438(8) 0.8033(8) -0.01243(18) 0.0176(8) Uani 1 1 d . . . H1 H 0.1341 0.6523 0.0136 0.021 Uiso 1 1 calc R . . N2 N 0.12858(8) 1.0097(8) 0.17856(19) 0.0178(8) Uani 1 1 d . . . H2A H 0.1334 1.1727 0.1915 0.021 Uiso 1 1 calc R . . N3 N 0.13313(8) 0.8588(8) 0.36774(19) 0.0201(8) Uani 1 1 d . . . H3A H 0.1297 0.7026 0.3890 0.024 Uiso 1 1 calc R . . O1 O 0.14432(7) 0.8929(7) -0.26695(16) 0.0203(7) Uani 1 1 d . . . O2 O 0.06726(7) 0.5292(7) -0.26440(17) 0.0247(8) Uani 1 1 d . . . O3 O 0.04199(7) 0.8983(8) -0.2160(2) 0.0320(8) Uani 1 1 d . . . O4 O 0.09115(7) 0.8989(8) -0.14085(18) 0.0302(8) Uani 1 1 d . . . O5 O 0.20493(7) 1.0271(8) -0.0569(2) 0.0376(9) Uani 1 1 d . . . O6 O 0.23394(7) 0.7022(7) -0.11166(17) 0.0252(8) Uani 1 1 d . . . O7 O 0.12832(7) 1.2462(7) 0.00452(17) 0.0224(7) Uani 1 1 d . . . O8 O 0.13807(8) 0.5815(7) 0.20291(18) 0.0266(8) Uani 1 1 d . . . O9 O 0.12216(8) 1.2948(7) 0.38101(19) 0.0298(8) Uani 1 1 d . . . O10 O 0.09095(7) 0.9837(7) 0.44316(16) 0.0228(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0230(19) 0.035(3) 0.024(2) 0.003(2) 0.0053(16) 0.005(2) C2 0.036(2) 0.039(4) 0.022(2) 0.004(2) 0.0094(18) 0.008(2) C3 0.043(3) 0.048(4) 0.035(2) 0.017(3) 0.015(2) 0.019(3) C4 0.031(2) 0.046(4) 0.051(3) 0.015(3) 0.016(2) -0.001(2) C5 0.022(2) 0.051(4) 0.048(3) 0.008(3) 0.0019(19) -0.005(2) C6 0.023(2) 0.039(4) 0.028(2) 0.008(2) -0.0011(16) 0.004(2) C7 0.028(2) 0.028(3) 0.0196(18) -0.0025(19) 0.0019(15) 0.004(2) C8 0.0219(19) 0.017(3) 0.0203(19) 0.0009(17) -0.0013(15) -0.0006(18) C9 0.026(2) 0.018(3) 0.0260(19) 0.0070(18) -0.0046(16) 0.0009(19) C10 0.024(2) 0.014(3) 0.035(2) -0.0024(19) -0.0023(17) 0.0003(18) C11 0.030(2) 0.032(4) 0.041(2) 0.002(2) -0.0085(19) -0.004(2) C12 0.030(2) 0.040(4) 0.030(2) -0.001(2) 0.0055(17) 0.000(2) C13 0.019(2) 0.035(4) 0.036(2) 0.004(2) -0.0073(17) -0.0012(19) C14 0.0229(19) 0.023(3) 0.0202(19) -0.0053(18) 0.0032(15) -0.0029(19) C15 0.0180(17) 0.017(3) 0.0158(17) -0.0049(16) 0.0023(13) 0.0005(17) C16 0.0193(19) 0.016(3) 0.0221(18) 0.0000(17) 0.0005(14) 0.0002(17) C17 0.0207(18) 0.007(3) 0.0249(18) 0.0004(17) 0.0007(14) 0.0015(16) C18 0.0207(19) 0.016(3) 0.040(2) -0.003(2) 0.0017(17) -0.0035(19) C19 0.020(2) 0.054(4) 0.050(3) -0.009(3) 0.0088(19) 0.001(2) C20 0.0160(17) 0.015(3) 0.0187(17) -0.0005(17) -0.0004(13) 0.0018(17) C21 0.0212(18) 0.023(3) 0.0152(17) -0.0030(16) -0.0007(14) -0.0026(17) C22 0.021(2) 0.048(4) 0.0201(19) -0.008(2) 0.0030(15) 0.006(2) C23 0.021(2) 0.089(6) 0.028(2) -0.004(3) -0.0030(17) 0.009(3) C24 0.028(2) 0.129(8) 0.023(2) -0.002(3) 0.0082(18) 0.018(3) C25 0.0220(17) 0.004(3) 0.0200(17) 0.0009(16) 0.0036(14) -0.0003(16) C26 0.0211(18) 0.031(3) 0.0171(17) 0.0012(18) 0.0008(14) -0.0004(19) C27 0.024(2) 0.028(3) 0.028(2) -0.002(2) -0.0010(16) 0.001(2) C28 0.0256(19) 0.015(3) 0.0178(17) 0.0030(17) -0.0013(15) -0.0012(18) C29 0.027(2) 0.010(3) 0.0239(19) -0.0009(17) 0.0029(16) 0.0045(17) C30 0.034(2) 0.038(4) 0.0193(18) -0.003(2) 0.0004(16) 0.001(2) C31 0.026(2) 0.023(3) 0.031(2) -0.003(2) 0.0056(16) 0.006(2) C32 0.034(2) 0.038(4) 0.0213(19) -0.001(2) -0.0007(17) 0.009(2) N1 0.0204(15) 0.017(2) 0.0152(15) 0.0039(14) 0.0001(12) 0.0007(15) N2 0.0226(16) 0.011(2) 0.0193(15) -0.0025(14) -0.0004(12) -0.0028(15) N3 0.0258(17) 0.015(2) 0.0194(15) 0.0049(15) 0.0050(13) -0.0007(16) O1 0.0241(14) 0.017(2) 0.0200(13) -0.0011(12) 0.0038(10) -0.0035(13) O2 0.0235(14) 0.025(2) 0.0259(14) -0.0026(14) -0.0001(11) -0.0024(14) O3 0.0193(14) 0.031(2) 0.0459(18) -0.0037(16) -0.0063(13) -0.0026(14) O4 0.0215(14) 0.040(2) 0.0290(15) -0.0141(15) -0.0047(11) 0.0088(14) O5 0.0256(16) 0.020(2) 0.067(2) -0.0170(19) -0.0032(15) -0.0010(15) O6 0.0183(14) 0.027(2) 0.0303(15) -0.0003(15) 0.0018(11) -0.0020(13) O7 0.0320(16) 0.014(2) 0.0210(13) 0.0014(12) 0.0020(11) 0.0010(13) O8 0.0394(17) 0.014(2) 0.0261(15) 0.0025(13) -0.0042(12) 0.0001(14) O9 0.0389(17) 0.018(2) 0.0326(16) -0.0004(14) 0.0086(13) -0.0001(15) O10 0.0253(14) 0.020(2) 0.0227(13) -0.0014(13) 0.0058(11) 0.0013(13) _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 C6 1.398(7) . ? C1 C2 1.414(6) . ? C1 C7 1.495(7) . ? C2 C3 1.341(8) . ? C2 H2 0.9500 . ? C3 C4 1.398(9) . ? C3 H3 0.9500 . ? C4 C5 1.415(7) . ? C4 H4 0.9500 . ? C5 C6 1.348(8) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.433(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.433(5) . ? C8 C9 1.518(6) . ? C8 C14 1.542(5) . ? C8 H8 1.0000 . ? C9 O2 1.427(6) . ? C9 C13 1.518(7) . ? C9 H9 1.0000 . ? C10 O3 1.416(7) . ? C10 O2 1.452(5) . ? C10 C11 1.502(6) . ? C10 C12 1.533(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O3 1.422(5) . ? C13 O4 1.435(5) . ? C13 H13 1.0000 . ? C14 O4 1.444(6) . ? C14 C15 1.529(5) . ? C14 H14 1.0000 . ? C15 N1 1.471(4) . ? C15 C16 1.531(6) . ? C15 H15 1.0000 . ? C16 C17 1.526(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O5 1.171(6) . ? C17 O6 1.343(5) . ? C18 O6 1.472(5) . ? C18 C19 1.528(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O7 1.215(6) . ? C20 N1 1.357(6) . ? C20 C21 1.548(5) . ? C21 N2 1.465(5) . ? C21 C22 1.554(6) . ? C21 H21 1.0000 . ? C22 C23 1.541(6) . ? C22 C24 1.546(6) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O8 1.222(6) . ? C25 N2 1.332(6) . ? C25 C26 1.532(5) . ? C26 N3 1.475(5) . ? C26 C27 1.515(6) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O9 1.216(6) . ? C28 O10 1.350(5) . ? C28 N3 1.355(6) . ? C29 O10 1.462(5) . ? C29 C31 1.527(6) . ? C29 C30 1.528(6) . ? C29 C32 1.532(6) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? N3 H3A 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 116.9(5) . . ? C6 C1 C7 122.1(4) . . ? C2 C1 C7 121.0(4) . . ? C3 C2 C1 121.2(5) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 122.0(4) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 116.9(5) . . ? C3 C4 H4 121.5 . . ? C5 C4 H4 121.5 . . ? C6 C5 C4 120.9(5) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 121.9(4) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? O1 C7 C1 108.8(4) . . ? O1 C7 H7A 109.9 . . ? C1 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O1 C8 C9 108.2(4) . . ? O1 C8 C14 109.3(3) . . ? C9 C8 C14 100.7(3) . . ? O1 C8 H8 112.7 . . ? C9 C8 H8 112.7 . . ? C14 C8 H8 112.7 . . ? O2 C9 C13 103.9(3) . . ? O2 C9 C8 112.5(4) . . ? C13 C9 C8 104.3(3) . . ? O2 C9 H9 111.9 . . ? C13 C9 H9 111.9 . . ? C8 C9 H9 111.9 . . ? O3 C10 O2 105.9(4) . . ? O3 C10 C11 109.2(4) . . ? O2 C10 C11 108.0(4) . . ? O3 C10 C12 111.7(4) . . ? O2 C10 C12 109.7(4) . . ? C11 C10 C12 112.0(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 O4 111.6(4) . . ? O3 C13 C9 103.1(4) . . ? O4 C13 C9 104.3(4) . . ? O3 C13 H13 112.4 . . ? O4 C13 H13 112.4 . . ? C9 C13 H13 112.4 . . ? O4 C14 C15 106.0(4) . . ? O4 C14 C8 105.1(3) . . ? C15 C14 C8 115.6(3) . . ? O4 C14 H14 110.0 . . ? C15 C14 H14 110.0 . . ? C8 C14 H14 110.0 . . ? N1 C15 C14 106.1(3) . . ? N1 C15 C16 111.5(3) . . ? C14 C15 C16 113.7(4) . . ? N1 C15 H15 108.5 . . ? C14 C15 H15 108.5 . . ? C16 C15 H15 108.5 . . ? C17 C16 C15 110.0(4) . . ? C17 C16 H16A 109.7 . . ? C15 C16 H16A 109.7 . . ? C17 C16 H16B 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? O5 C17 O6 124.7(4) . . ? O5 C17 C16 124.9(4) . . ? O6 C17 C16 110.5(4) . . ? O6 C18 C19 105.8(4) . . ? O6 C18 H18A 110.6 . . ? C19 C18 H18A 110.6 . . ? O6 C18 H18B 110.6 . . ? C19 C18 H18B 110.6 . . ? H18A C18 H18B 108.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O7 C20 N1 125.7(3) . . ? O7 C20 C21 122.4(4) . . ? N1 C20 C21 112.0(4) . . ? N2 C21 C20 109.8(3) . . ? N2 C21 C22 110.9(3) . . ? C20 C21 C22 109.2(3) . . ? N2 C21 H21 109.0 . . ? C20 C21 H21 109.0 . . ? C22 C21 H21 109.0 . . ? C23 C22 C24 109.3(4) . . ? C23 C22 C21 107.5(4) . . ? C24 C22 C21 108.9(4) . . ? C23 C22 H22 110.3 . . ? C24 C22 H22 110.3 . . ? C21 C22 H22 110.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 N2 123.8(4) . . ? O8 C25 C26 120.7(4) . . ? N2 C25 C26 115.4(4) . . ? N3 C26 C27 110.1(4) . . ? N3 C26 C25 106.8(3) . . ? C27 C26 C25 111.5(4) . . ? N3 C26 H26 109.5 . . ? C27 C26 H26 109.5 . . ? C25 C26 H26 109.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O9 C28 O10 125.1(4) . . ? O9 C28 N3 124.8(4) . . ? O10 C28 N3 110.2(4) . . ? O10 C29 C31 103.5(4) . . ? O10 C29 C30 110.2(3) . . ? C31 C29 C30 110.4(3) . . ? O10 C29 C32 110.5(3) . . ? C31 C29 C32 109.8(4) . . ? C30 C29 C32 112.1(4) . . ? 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 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C20 N1 C15 122.6(4) . . ? C20 N1 H1 118.7 . . ? C15 N1 H1 118.7 . . ? C25 N2 C21 119.9(4) . . ? C25 N2 H2A 120.1 . . ? C21 N2 H2A 120.1 . . ? C28 N3 C26 121.1(4) . . ? C28 N3 H3A 119.5 . . ? C26 N3 H3A 119.5 . . ? C7 O1 C8 113.4(3) . . ? C9 O2 C10 108.9(4) . . ? C10 O3 C13 108.7(4) . . ? C13 O4 C14 111.5(3) . . ? C17 O6 C18 113.6(4) . . ? C28 O10 C29 120.4(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 C6 C1 C2 C3 4.2(8) . . . . ? C7 C1 C2 C3 -176.9(5) . . . . ? C1 C2 C3 C4 -4.7(8) . . . . ? C2 C3 C4 C5 4.2(8) . . . . ? C3 C4 C5 C6 -3.5(9) . . . . ? C4 C5 C6 C1 3.4(9) . . . . ? C2 C1 C6 C5 -3.6(8) . . . . ? C7 C1 C6 C5 177.5(5) . . . . ? C6 C1 C7 O1 32.7(6) . . . . ? C2 C1 C7 O1 -146.2(4) . . . . ? O1 C8 C9 O2 170.9(3) . . . . ? C14 C8 C9 O2 -74.6(4) . . . . ? O1 C8 C9 C13 -77.2(4) . . . . ? C14 C8 C9 C13 37.3(4) . . . . ? O2 C9 C13 O3 -29.1(4) . . . . ? C8 C9 C13 O3 -147.1(4) . . . . ? O2 C9 C13 O4 87.6(4) . . . . ? C8 C9 C13 O4 -30.5(4) . . . . ? O1 C8 C14 O4 82.7(4) . . . . ? C9 C8 C14 O4 -31.0(4) . . . . ? O1 C8 C14 C15 -33.8(5) . . . . ? C9 C8 C14 C15 -147.5(4) . . . . ? O4 C14 C15 N1 66.0(4) . . . . ? C8 C14 C15 N1 -178.0(4) . . . . ? O4 C14 C15 C16 -171.1(3) . . . . ? C8 C14 C15 C16 -55.2(5) . . . . ? N1 C15 C16 C17 -84.4(4) . . . . ? C14 C15 C16 C17 155.7(4) . . . . ? C15 C16 C17 O5 11.0(6) . . . . ? C15 C16 C17 O6 -169.9(3) . . . . ? O7 C20 C21 N2 -76.1(5) . . . . ? N1 C20 C21 N2 105.1(4) . . . . ? O7 C20 C21 C22 45.6(5) . . . . ? N1 C20 C21 C22 -133.1(4) . . . . ? N2 C21 C22 C23 -172.1(4) . . . . ? C20 C21 C22 C23 66.8(5) . . . . ? N2 C21 C22 C24 -53.8(6) . . . . ? C20 C21 C22 C24 -174.9(5) . . . . ? O8 C25 C26 N3 -80.9(5) . . . . ? N2 C25 C26 N3 95.7(4) . . . . ? O8 C25 C26 C27 39.4(5) . . . . ? N2 C25 C26 C27 -144.0(4) . . . . ? O7 C20 N1 C15 -12.0(6) . . . . ? C21 C20 N1 C15 166.8(3) . . . . ? C14 C15 N1 C20 -102.1(4) . . . . ? C16 C15 N1 C20 133.7(4) . . . . ? O8 C25 N2 C21 7.8(6) . . . . ? C26 C25 N2 C21 -168.7(3) . . . . ? C20 C21 N2 C25 -109.8(4) . . . . ? C22 C21 N2 C25 129.4(4) . . . . ? O9 C28 N3 C26 -12.9(6) . . . . ? O10 C28 N3 C26 168.1(3) . . . . ? C27 C26 N3 C28 141.2(4) . . . . ? C25 C26 N3 C28 -97.6(5) . . . . ? C1 C7 O1 C8 -173.8(3) . . . . ? C9 C8 O1 C7 -86.7(4) . . . . ? C14 C8 O1 C7 164.6(3) . . . . ? C13 C9 O2 C10 17.8(4) . . . . ? C8 C9 O2 C10 130.0(4) . . . . ? O3 C10 O2 C9 0.3(4) . . . . ? C11 C10 O2 C9 117.2(4) . . . . ? C12 C10 O2 C9 -120.5(4) . . . . ? O2 C10 O3 C13 -20.0(4) . . . . ? C11 C10 O3 C13 -136.1(4) . . . . ? C12 C10 O3 C13 99.4(4) . . . . ? O4 C13 O3 C10 -80.9(5) . . . . ? C9 C13 O3 C10 30.5(5) . . . . ? O3 C13 O4 C14 121.1(4) . . . . ? C9 C13 O4 C14 10.5(5) . . . . ? C15 C14 O4 C13 136.2(4) . . . . ? C8 C14 O4 C13 13.3(5) . . . . ? O5 C17 O6 C18 -2.1(6) . . . . ? C16 C17 O6 C18 178.8(3) . . . . ? C19 C18 O6 C17 -172.0(4) . . . . ? O9 C28 O10 C29 -1.7(6) . . . . ? N3 C28 O10 C29 177.2(3) . . . . ? C31 C29 O10 C28 179.0(3) . . . . ? C30 C29 O10 C28 -62.9(5) . . . . ? C32 C29 O10 C28 61.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.513 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.124 _iucr_refine_instructions_details ; TITL c2 in C2 CELL 0.71073 41.0431 5.0993 16.3343 90.000 90.000 90.000 ZERR 4.00 0.0082 0.0010 0.0033 0.000 0.000 0.000 LATT -7 SYMM - X, Y, - Z SFAC C H N O UNIT 128 192 12 40 MERG 2 OMIT -2.00 50.00 OMIT -3 1 1 OMIT 1 1 0 OMIT -3 -1 1 OMIT -10 -2 2 OMIT -4 2 3 OMIT 2 2 0 OMIT -8 -2 3 OMIT -5 1 1 OMIT -5 -1 1 OMIT -1 -1 1 OMIT -1 1 1 OMIT 3 -1 0 OMIT 0 0 1 OMIT -5 3 1 OMIT -2 2 2 FMAP 2 PLAN 2 SIZE 0.15 0.23 0.36 ACTA HTAB 2.00000 BOND $H CONF L.S. 8 TEMP -100.00 WGHT 0.106800 13.695001 EXTI 0.004485 FVAR 0.10773 C1 1 0.182790 1.064232 -0.362250 11.00000 0.02302 0.03476 = 0.02379 0.00342 0.00454 0.00390 C2 1 0.187730 1.163430 -0.442072 11.00000 0.03563 0.03829 = 0.02249 0.00380 0.00935 0.00900 AFIX 43 H2 2 0.174547 1.101058 -0.485731 11.00000 -1.20000 AFIX 0 C3 1 0.210682 1.343933 -0.457285 11.00000 0.04371 0.04782 = 0.03436 0.01796 0.01498 0.01923 AFIX 43 H3 2 0.214483 1.396905 -0.512220 11.00000 -1.20000 AFIX 0 C4 1 0.229189 1.456485 -0.394590 11.00000 0.03149 0.04369 = 0.05120 0.01450 0.01591 -0.00042 AFIX 43 H4 2 0.244460 1.592189 -0.405337 11.00000 -1.20000 AFIX 0 C5 1 0.224166 1.359274 -0.314379 11.00000 0.02232 0.05020 = 0.04705 0.00795 0.00184 -0.00562 AFIX 43 H5 2 0.237074 1.424436 -0.270596 11.00000 -1.20000 AFIX 0 C6 1 0.201318 1.175489 -0.299257 11.00000 0.02345 0.03982 = 0.02780 0.00673 -0.00057 0.00328 AFIX 43 H6 2 0.197709 1.120148 -0.244468 11.00000 -1.20000 AFIX 0 C7 1 0.158336 0.853095 -0.346281 11.00000 0.02649 0.02777 = 0.02018 -0.00239 0.00207 0.00278 AFIX 23 H7A 2 0.141062 0.858258 -0.388553 11.00000 -1.20000 H7B 2 0.169038 0.679279 -0.348687 11.00000 -1.20000 AFIX 0 C8 1 0.122971 0.684667 -0.241975 11.00000 0.02149 0.01711 = 0.01965 0.00148 -0.00133 -0.00126 AFIX 13 H8 2 0.131096 0.507550 -0.258525 11.00000 -1.20000 AFIX 0 C9 1 0.089158 0.743370 -0.275047 11.00000 0.02567 0.01903 = 0.02504 0.00637 -0.00443 0.00153 AFIX 13 H9 2 0.089853 0.804478 -0.333194 11.00000 -1.20000 AFIX 0 C10 1 0.037486 0.625195 -0.226988 11.00000 0.02373 0.01349 = 0.03481 -0.00295 -0.00212 0.00072 C11 1 0.010018 0.580344 -0.286066 11.00000 0.02941 0.03134 = 0.04042 0.00185 -0.00771 -0.00341 AFIX 137 H11A 2 -0.010480 0.639068 -0.261356 11.00000 -1.50000 H11B 2 0.008540 0.393047 -0.298986 11.00000 -1.50000 H11C 2 0.014067 0.679644 -0.336416 11.00000 -1.50000 AFIX 0 C12 1 0.031761 0.484122 -0.145370 11.00000 0.02984 0.04071 = 0.03098 -0.00051 0.00614 -0.00045 AFIX 137 H12A 2 0.050305 0.515524 -0.108870 11.00000 -1.50000 H12B 2 0.029500 0.295393 -0.155167 11.00000 -1.50000 H12C 2 0.011817 0.551265 -0.119897 11.00000 -1.50000 AFIX 0 C13 1 0.075912 0.952776 -0.218120 11.00000 0.01929 0.03283 = 0.03694 0.00323 -0.00695 -0.00125 AFIX 13 H13 2 0.080686 1.134101 -0.238114 11.00000 -1.20000 AFIX 0 C14 1 0.116701 0.706465 -0.149055 11.00000 0.02307 0.02276 = 0.01958 -0.00600 0.00286 -0.00269 AFIX 13 H14 2 0.109198 0.533648 -0.127103 11.00000 -1.20000 AFIX 0 C15 1 0.145318 0.808510 -0.098030 11.00000 0.01752 0.01914 = 0.01522 -0.00486 0.00219 0.00053 AFIX 13 H15 2 0.149551 0.994846 -0.113872 11.00000 -1.20000 AFIX 0 C16 1 0.176744 0.653161 -0.109335 11.00000 0.01897 0.01180 = 0.02658 -0.00295 0.00081 0.00031 AFIX 43 H16 2 0.177777 0.475542 -0.126689 11.00000 -1.20000 AFIX 0 C17 1 0.206207 0.821937 -0.088984 11.00000 0.02082 0.00687 = 0.02412 0.00016 0.00027 0.00119 C18 1 0.263440 0.857894 -0.095108 11.00000 0.02036 0.01696 = 0.04033 -0.00185 0.00109 -0.00327 AFIX 23 H18A 2 0.267182 0.873559 -0.035433 11.00000 -1.20000 H18B 2 0.261335 1.036046 -0.118609 11.00000 -1.20000 AFIX 0 C19 1 0.291380 0.709486 -0.135763 11.00000 0.01932 0.05415 = 0.04909 -0.00894 0.00833 0.00091 AFIX 137 H19A 2 0.295365 0.545538 -0.106103 11.00000 -1.50000 H19B 2 0.311105 0.817726 -0.134639 11.00000 -1.50000 H19C 2 0.285613 0.669889 -0.192656 11.00000 -1.50000 AFIX 0 C20 1 0.124624 1.021807 0.027953 11.00000 0.01560 0.01485 = 0.01890 -0.00033 -0.00051 0.00175 C21 1 0.107000 0.955016 0.109225 11.00000 0.02179 0.02269 = 0.01523 -0.00310 -0.00074 -0.00196 AFIX 13 H21 2 0.101271 0.764411 0.109429 11.00000 -1.20000 AFIX 0 C22 1 0.075116 1.119726 0.115233 11.00000 0.02112 0.04769 = 0.01967 -0.00808 0.00345 0.00558 AFIX 13 H22 2 0.079997 1.310453 0.107996 11.00000 -1.20000 AFIX 0 C23 1 0.051961 1.023563 0.047490 11.00000 0.02051 0.08521 = 0.02832 -0.00356 -0.00277 0.00724 AFIX 137 H23A 2 0.040143 0.868278 0.066665 11.00000 -1.50000 H23B 2 0.064618 0.978500 -0.001401 11.00000 -1.50000 H23C 2 0.036377 1.162672 0.034064 11.00000 -1.50000 AFIX 0 C24 1 0.059302 1.070160 0.199746 11.00000 0.02813 0.12616 = 0.02280 -0.00272 0.00863 0.01770 AFIX 137 H24A 2 0.035932 1.108363 0.196720 11.00000 -1.50000 H24B 2 0.069475 1.184307 0.240689 11.00000 -1.50000 H24C 2 0.062476 0.886394 0.215392 11.00000 -1.50000 AFIX 0 C25 1 0.140882 0.811836 0.221936 11.00000 0.02189 0.00410 = 0.01967 0.00118 0.00334 -0.00021 C26 1 0.157562 0.890505 0.302357 11.00000 0.02092 0.02996 = 0.01650 0.00114 0.00084 -0.00044 AFIX 13 H26 2 0.164493 1.078256 0.299317 11.00000 -1.20000 AFIX 0 C27 1 0.186973 0.719058 0.319609 11.00000 0.02389 0.02939 = 0.02782 -0.00186 -0.00071 0.00035 AFIX 137 H27A 2 0.197603 0.778142 0.370066 11.00000 -1.50000 H27B 2 0.202363 0.731758 0.273909 11.00000 -1.50000 H27C 2 0.179955 0.536508 0.325997 11.00000 -1.50000 AFIX 0 C28 1 0.115793 1.066911 0.395703 11.00000 0.02535 0.01478 = 0.01806 0.00312 -0.00076 -0.00120 C29 1 0.069598 1.173108 0.483582 11.00000 0.02696 0.00922 = 0.02409 -0.00104 0.00256 0.00417 C30 1 0.088990 1.337785 0.544629 11.00000 0.03416 0.03746 = 0.01910 -0.00457 -0.00035 0.00146 AFIX 137 H30A 2 0.101461 1.221742 0.580758 11.00000 -1.50000 H30B 2 0.073978 1.444108 0.577417 11.00000 -1.50000 H30C 2 0.103973 1.453161 0.514881 11.00000 -1.50000 AFIX 0 C31 1 0.044969 1.000781 0.528562 11.00000 0.02655 0.02385 = 0.02958 -0.00342 0.00599 0.00602 AFIX 137 H31A 2 0.030949 0.912263 0.488626 11.00000 -1.50000 H31B 2 0.031582 1.110072 0.564672 11.00000 -1.50000 H31C 2 0.056578 0.869460 0.561243 11.00000 -1.50000 AFIX 0 C32 1 0.051932 1.342703 0.420185 11.00000 0.03343 0.03766 = 0.02114 -0.00096 -0.00025 0.00893 AFIX 137 H32A 2 0.067658 1.458422 0.393108 11.00000 -1.50000 H32B 2 0.035269 1.448768 0.447573 11.00000 -1.50000 H32C 2 0.041567 1.229432 0.379310 11.00000 -1.50000 AFIX 0 N1 3 0.134365 0.803697 -0.012309 11.00000 0.02046 0.01740 = 0.01519 0.00336 0.00027 0.00050 AFIX 43 H1 2 0.134139 0.652823 0.013838 11.00000 -1.20000 AFIX 0 N2 3 0.128547 1.010093 0.178437 11.00000 0.02252 0.01087 = 0.01974 -0.00235 -0.00041 -0.00284 AFIX 43 H2A 2 0.133359 1.173093 0.191354 11.00000 -1.20000 AFIX 0 N3 3 0.133114 0.858818 0.367669 11.00000 0.02586 0.01379 = 0.01915 0.00415 0.00513 -0.00074 AFIX 43 H3A 2 0.129694 0.702510 0.388823 11.00000 -1.20000 AFIX 0 O1 4 0.144336 0.892573 -0.266980 11.00000 0.02405 0.01718 = 0.01995 -0.00123 0.00395 -0.00421 O2 4 0.067280 0.529065 -0.264372 11.00000 0.02302 0.02442 = 0.02530 -0.00311 -0.00004 -0.00178 O3 4 0.042026 0.898413 -0.216075 11.00000 0.01955 0.03068 = 0.04595 -0.00318 -0.00623 -0.00235 O4 4 0.091115 0.898466 -0.140791 11.00000 0.02110 0.03989 = 0.02906 -0.01431 -0.00488 0.00785 O5 4 0.204922 1.027383 -0.056941 11.00000 0.02558 0.02080 = 0.06618 -0.01661 -0.00370 -0.00154 O6 4 0.233944 0.702128 -0.111673 11.00000 0.01811 0.02763 = 0.03001 -0.00053 0.00179 -0.00174 O7 4 0.128294 1.245946 0.004541 11.00000 0.03211 0.01369 = 0.02125 0.00113 0.00167 0.00104 O8 4 0.138068 0.581440 0.202890 11.00000 0.03952 0.01477 = 0.02571 0.00243 -0.00424 -0.00041 O9 4 0.122180 1.294582 0.381123 11.00000 0.03858 0.01771 = 0.03202 -0.00019 0.00825 0.00078 O10 4 0.090961 0.983494 0.443112 11.00000 0.02518 0.02035 = 0.02251 -0.00163 0.00562 0.00114 HKLF 4 REM c2 in C2 REM R1 = 0.0559 for 4923 Fo > 4sig(Fo) and 0.0658 for all 5098 data REM 416 parameters refined using 1 restraints END WGHT 0.1067 13.7120 REM Highest difference peak 0.508, deepest hole -0.416, 1-sigma level 0.126 Q1 1 0.1589 0.3668 0.2188 11.00000 0.05 0.51 Q2 1 0.1775 0.4926 -0.0731 11.00000 0.05 0.50 ; _database_code_depnum_ccdc_archive 'CCDC 936825' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sachin3 #TrackingRef '12088_web_deposit_cif_file_0_SachinA.Pawar_1340367865.SACHIN3_final.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H34 N O8.50' _chemical_formula_weight 472.52 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.2847(14) _cell_length_b 19.642(3) _cell_length_c 27.419(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5000.4(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18067 _cell_measurement_theta_min 1.28 _cell_measurement_theta_max 25.78 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not mesaured' _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9887 _exptl_absorpt_correction_T_max 0.9972 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18067 _diffrn_reflns_av_R_equivalents 0.1003 _diffrn_reflns_av_sigmaI/netI 0.1004 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.78 _reflns_number_total 5333 _reflns_number_gt 2861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0662P)^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 none _refine_ls_extinction_coef none _refine_ls_number_reflns 5333 _refine_ls_number_parameters 624 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1316 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.957 _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 O1A O 0.2867(4) 0.81053(18) 0.84443(14) 0.0355(10) Uani 1 1 d . . . O2A O 0.2765(4) 0.69588(18) 0.85500(14) 0.0351(10) Uani 1 1 d . . . O3A O 0.5341(4) 0.80914(17) 0.85559(13) 0.0302(9) Uani 1 1 d . . . O4A O 0.6640(4) 0.67704(16) 0.84232(13) 0.0296(9) Uani 1 1 d . . . O5A O 0.8958(4) 0.77453(19) 0.99934(15) 0.0406(10) Uani 1 1 d . . . O6A O 0.9262(4) 0.66278(19) 0.99503(15) 0.0451(11) Uani 1 1 d . . . N1A N 0.6738(5) 0.8317(2) 0.95523(17) 0.0292(11) Uani 1 1 d D . . C1A C 0.1008(7) 0.7499(3) 0.8015(2) 0.0482(17) Uani 1 1 d . . . H1A1 H 0.0356 0.7108 0.8035 0.072 Uiso 1 1 calc R . . H1A2 H 0.1663 0.7441 0.7738 0.072 Uiso 1 1 calc R . . H1A3 H 0.0445 0.7917 0.7971 0.072 Uiso 1 1 calc R . . C2A C 0.0980(7) 0.7638(3) 0.8929(2) 0.0516(18) Uani 1 1 d . . . H2A1 H 0.1611 0.7713 0.9211 0.077 Uiso 1 1 calc R . . H2A2 H 0.0400 0.7229 0.8982 0.077 Uiso 1 1 calc R . . H2A3 H 0.0344 0.8032 0.8888 0.077 Uiso 1 1 calc R . . C3A C 0.1874(6) 0.7550(3) 0.8481(2) 0.0300(13) Uani 1 1 d . . . C4A C 0.4195(5) 0.7857(2) 0.82603(19) 0.0283(13) Uani 1 1 d . . . H4A H 0.4337 0.7990 0.7911 0.034 Uiso 1 1 calc R . . C5A C 0.4129(6) 0.7076(2) 0.8319(2) 0.0283(13) Uani 1 1 d . . . H5A H 0.4232 0.6828 0.8003 0.034 Uiso 1 1 calc R . . C6A C 0.5331(5) 0.6916(3) 0.8677(2) 0.0290(13) Uani 1 1 d . . . H6A H 0.5059 0.6540 0.8904 0.035 Uiso 1 1 calc R . . C7A C 0.5476(5) 0.7600(2) 0.89444(19) 0.0261(12) Uani 1 1 d . . . H7A H 0.4651 0.7655 0.9176 0.031 Uiso 1 1 calc R . . C8A C 0.6742(6) 0.6062(2) 0.8307(2) 0.0353(14) Uani 1 1 d . . . H8A1 H 0.5941 0.5930 0.8088 0.042 Uiso 1 1 calc R . . H8A2 H 0.6671 0.5787 0.8609 0.042 Uiso 1 1 calc R . . C9A C 0.8168(6) 0.5930(3) 0.8059(2) 0.0306(13) Uani 1 1 d . . . C10A C 0.8316(7) 0.5935(3) 0.7563(2) 0.0379(15) Uani 1 1 d . . . H10A H 0.7497 0.6024 0.7365 0.046 Uiso 1 1 calc R . . C11A C 0.9636(8) 0.5814(3) 0.7342(3) 0.0517(19) Uani 1 1 d . . . H11A H 0.9724 0.5826 0.6997 0.062 Uiso 1 1 calc R . . C12A C 1.0815(8) 0.5676(3) 0.7630(3) 0.054(2) Uani 1 1 d . . . H12A H 1.1720 0.5586 0.7482 0.065 Uiso 1 1 calc R . . C13A C 1.0692(7) 0.5668(3) 0.8132(3) 0.0481(17) Uani 1 1 d . . . H13A H 1.1514 0.5576 0.8328 0.058 Uiso 1 1 calc R . . C14A C 0.9362(6) 0.5795(2) 0.8354(2) 0.0389(15) Uani 1 1 d . . . H14A H 0.9272 0.5789 0.8699 0.047 Uiso 1 1 calc R . . C15A C 0.6897(5) 0.7709(2) 0.92207(19) 0.0273(12) Uani 1 1 d . . . H15A H 0.7694 0.7792 0.8983 0.033 Uiso 1 1 calc R . . C16A C 0.6704(6) 0.9008(2) 0.9327(2) 0.0354(14) Uani 1 1 d . . . H16A H 0.6486 0.9349 0.9582 0.042 Uiso 1 1 calc R . . H16B H 0.5922 0.9025 0.9082 0.042 Uiso 1 1 calc R . . C17A C 0.8109(6) 0.9193(3) 0.9084(2) 0.0349(14) Uani 1 1 d . . . C18A C 0.9286(6) 0.9386(3) 0.9364(2) 0.0487(17) Uani 1 1 d . . . H18A H 0.9204 0.9405 0.9709 0.058 Uiso 1 1 calc R . . C19A C 1.0571(8) 0.9550(4) 0.9143(3) 0.067(2) Uani 1 1 d . . . H19A H 1.1371 0.9681 0.9337 0.080 Uiso 1 1 calc R . . C20A C 1.0709(8) 0.9528(3) 0.8647(3) 0.0568(19) Uani 1 1 d . . . H20A H 1.1603 0.9639 0.8498 0.068 Uiso 1 1 calc R . . C21A C 0.9538(7) 0.9342(3) 0.8362(3) 0.0508(17) Uani 1 1 d . . . H21A H 0.9624 0.9334 0.8017 0.061 Uiso 1 1 calc R . . C22A C 0.8251(7) 0.9170(3) 0.8580(2) 0.0387(15) Uani 1 1 d . . . H22A H 0.7457 0.9034 0.8385 0.046 Uiso 1 1 calc R . . C23A C 0.7262(5) 0.7096(2) 0.9535(2) 0.0275(13) Uani 1 1 d . . . H23A H 0.7384 0.6695 0.9320 0.033 Uiso 1 1 calc R . . H23B H 0.6435 0.7002 0.9753 0.033 Uiso 1 1 calc R . . C24A C 0.8613(6) 0.7171(3) 0.9848(2) 0.0331(14) Uani 1 1 d . . . O1B O -0.2022(4) 0.70691(17) 0.66201(14) 0.0353(9) Uani 1 1 d . . . O2B O -0.2211(4) 0.82122(18) 0.65218(13) 0.0316(9) Uani 1 1 d . . . O3B O 0.0389(4) 0.71376(17) 0.64050(13) 0.0322(9) Uani 1 1 d . . . O4B O 0.1677(4) 0.84473(16) 0.65987(13) 0.0316(9) Uani 1 1 d . . . O5B O 0.4574(4) 0.87613(19) 0.53286(16) 0.0460(11) Uani 1 1 d . . . O6B O 0.4223(4) 0.76963(17) 0.50715(14) 0.0372(10) Uani 1 1 d . . . N1B N 0.1806(5) 0.7022(2) 0.54162(16) 0.0275(11) Uani 1 1 d D . . C1B C -0.3726(7) 0.7661(3) 0.7122(2) 0.058(2) Uani 1 1 d . . . H1B1 H -0.2978 0.7732 0.7369 0.087 Uiso 1 1 calc R . . H1B2 H -0.4256 0.7242 0.7195 0.087 Uiso 1 1 calc R . . H1B3 H -0.4392 0.8048 0.7124 0.087 Uiso 1 1 calc R . . C2B C -0.4090(7) 0.7507(3) 0.6216(3) 0.0576(19) Uani 1 1 d . . . H2B1 H -0.4681 0.7103 0.6279 0.086 Uiso 1 1 calc R . . H2B2 H -0.3564 0.7448 0.5909 0.086 Uiso 1 1 calc R . . H2B3 H -0.4713 0.7908 0.6192 0.086 Uiso 1 1 calc R . . C3B C -0.3037(6) 0.7603(3) 0.6627(2) 0.0355(14) Uani 1 1 d . . . C4B C -0.0648(6) 0.7331(3) 0.6757(2) 0.0326(13) Uani 1 1 d . . . H4B H -0.0366 0.7180 0.7092 0.039 Uiso 1 1 calc R . . C5B C -0.0803(6) 0.8108(2) 0.6727(2) 0.0291(13) Uani 1 1 d . . . H5B H -0.0682 0.8336 0.7051 0.035 Uiso 1 1 calc R . . C6B C 0.0344(5) 0.8325(3) 0.6356(2) 0.0307(13) Uani 1 1 d . . . H6B H 0.0028 0.8724 0.6157 0.037 Uiso 1 1 calc R . . C7B C 0.0495(5) 0.7681(3) 0.60507(19) 0.0278(13) Uani 1 1 d . . . H7B H -0.0332 0.7650 0.5818 0.033 Uiso 1 1 calc R . . C8B C 0.1783(6) 0.9144(3) 0.6753(3) 0.0471(17) Uani 1 1 d . . . H8B1 H 0.1030 0.9243 0.6999 0.057 Uiso 1 1 calc R . . H8B2 H 0.1637 0.9451 0.6472 0.057 Uiso 1 1 calc R . . C9B C 0.3259(6) 0.9261(3) 0.6972(2) 0.0337(14) Uani 1 1 d . . . C10B C 0.4409(7) 0.9386(3) 0.6668(2) 0.0440(16) Uani 1 1 d . . . H10B H 0.4274 0.9390 0.6325 0.053 Uiso 1 1 calc R . . C11B C 0.5776(7) 0.9507(3) 0.6865(3) 0.057(2) Uani 1 1 d . . . H11B H 0.6576 0.9593 0.6658 0.068 Uiso 1 1 calc R . . C12B C 0.5944(8) 0.9499(3) 0.7367(4) 0.061(2) Uani 1 1 d . . . H12B H 0.6866 0.9585 0.7504 0.074 Uiso 1 1 calc R . . C13B C 0.4811(8) 0.9372(3) 0.7664(3) 0.0541(19) Uani 1 1 d . . . H13B H 0.4946 0.9367 0.8007 0.065 Uiso 1 1 calc R . . C14B C 0.3469(7) 0.9251(3) 0.7474(2) 0.0390(16) Uani 1 1 d . . . H14B H 0.2682 0.9160 0.7685 0.047 Uiso 1 1 calc R . . C15B C 0.1891(5) 0.7599(2) 0.57730(19) 0.0283(13) Uani 1 1 d . . . H15B H 0.2684 0.7505 0.6010 0.034 Uiso 1 1 calc R . . C16B C 0.1726(6) 0.6312(2) 0.5622(2) 0.0304(13) Uani 1 1 d . . . H16C H 0.1524 0.5988 0.5354 0.037 Uiso 1 1 calc R . . H16D H 0.0914 0.6288 0.5856 0.037 Uiso 1 1 calc R . . C17B C 0.3095(6) 0.6094(3) 0.5880(2) 0.0330(14) Uani 1 1 d . . . C18B C 0.3154(7) 0.6059(3) 0.6382(2) 0.0411(15) Uani 1 1 d . . . H18B H 0.2343 0.6185 0.6573 0.049 Uiso 1 1 calc R . . C19B C 0.4407(8) 0.5838(3) 0.6606(3) 0.0511(18) Uani 1 1 d . . . H19B H 0.4450 0.5814 0.6952 0.061 Uiso 1 1 calc R . . C20B C 0.5573(8) 0.5655(3) 0.6339(3) 0.059(2) Uani 1 1 d . . . H20B H 0.6425 0.5507 0.6499 0.070 Uiso 1 1 calc R . . C21B C 0.5532(7) 0.5681(3) 0.5842(3) 0.062(2) Uani 1 1 d . . . H21B H 0.6351 0.5550 0.5657 0.074 Uiso 1 1 calc R . . C22B C 0.4281(6) 0.5902(3) 0.5604(2) 0.0453(16) Uani 1 1 d . . . H22B H 0.4245 0.5921 0.5258 0.054 Uiso 1 1 calc R . . C23B C 0.2270(5) 0.8248(3) 0.5480(2) 0.0344(14) Uani 1 1 d . . . H23C H 0.2162 0.8650 0.5694 0.041 Uiso 1 1 calc R . . H23D H 0.1577 0.8297 0.5207 0.041 Uiso 1 1 calc R . . C24B C 0.3825(6) 0.8238(3) 0.5269(2) 0.0327(14) Uani 1 1 d . . . O1W O 0.8520(5) 0.5304(2) 0.9768(2) 0.0740(16) Uani 1 1 d . . . O2W O 1.2974(5) 0.5893(2) 0.94064(19) 0.0736(15) Uani 1 1 d . . . O3W O 0.7471(4) 0.8732(2) 0.55511(15) 0.0439(11) Uani 1 1 d . . . O4W O 0.4312(5) 1.0163(2) 0.55382(16) 0.0600(13) Uani 1 1 d . . . O5W O 0.0939(5) 0.4912(2) 0.92774(18) 0.0715(15) Uani 1 1 d . . . H1BY H 0.099(3) 0.706(2) 0.5196(14) 0.029(14) Uiso 1 1 d D . . H1AX H 0.584(3) 0.829(3) 0.9732(18) 0.053(18) Uiso 1 1 d D . . H1AY H 0.758(3) 0.826(2) 0.9755(15) 0.029(15) Uiso 1 1 d D . . H1BX H 0.263(4) 0.705(3) 0.5201(16) 0.049(18) Uiso 1 1 d 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 O1A 0.020(2) 0.035(2) 0.051(3) 0.0027(18) 0.0026(19) -0.0020(16) O2A 0.017(2) 0.037(2) 0.051(3) 0.0071(18) -0.0015(19) 0.0002(16) O3A 0.023(2) 0.031(2) 0.036(2) 0.0082(17) -0.0024(19) -0.0007(16) O4A 0.0204(19) 0.0269(19) 0.041(2) -0.0047(17) 0.0069(18) 0.0008(16) O5A 0.027(2) 0.042(2) 0.052(3) 0.000(2) -0.014(2) -0.0047(19) O6A 0.028(2) 0.047(2) 0.060(3) -0.001(2) -0.020(2) 0.002(2) N1A 0.017(2) 0.035(3) 0.036(3) -0.006(2) 0.001(3) -0.001(2) C1A 0.047(4) 0.044(3) 0.054(4) 0.002(3) -0.014(4) -0.001(3) C2A 0.034(4) 0.064(4) 0.057(4) 0.007(3) 0.010(3) 0.005(3) C3A 0.020(3) 0.032(3) 0.037(3) 0.002(2) -0.003(3) 0.000(2) C4A 0.016(3) 0.043(3) 0.026(3) 0.001(3) 0.000(3) 0.003(3) C5A 0.023(3) 0.033(3) 0.029(3) -0.003(2) 0.001(3) 0.006(3) C6A 0.020(3) 0.033(3) 0.034(3) 0.003(2) -0.002(3) 0.000(2) C7A 0.015(3) 0.031(3) 0.033(3) 0.003(2) 0.003(3) 0.001(2) C8A 0.024(3) 0.024(3) 0.057(4) -0.002(3) 0.004(3) -0.001(2) C9A 0.032(3) 0.024(3) 0.036(4) -0.001(2) 0.005(3) 0.001(3) C10A 0.046(4) 0.028(3) 0.039(4) -0.001(3) 0.002(3) 0.003(3) C11A 0.067(5) 0.038(3) 0.050(4) -0.005(3) 0.029(4) 0.002(3) C12A 0.044(4) 0.036(3) 0.083(6) 0.002(4) 0.033(5) 0.005(3) C13A 0.028(4) 0.044(4) 0.072(5) 0.009(3) -0.001(4) 0.002(3) C14A 0.039(4) 0.032(3) 0.046(4) 0.005(3) 0.003(4) 0.006(3) C15A 0.020(3) 0.032(3) 0.030(3) -0.004(2) -0.001(3) -0.001(2) C16A 0.024(3) 0.030(3) 0.051(4) -0.004(3) 0.004(3) -0.001(3) C17A 0.031(3) 0.026(3) 0.048(4) 0.004(3) -0.002(3) -0.001(2) C18A 0.041(4) 0.056(4) 0.050(4) -0.005(3) 0.006(4) -0.017(3) C19A 0.044(4) 0.087(5) 0.069(6) -0.005(4) -0.003(4) -0.032(4) C20A 0.047(4) 0.060(4) 0.064(5) -0.001(4) 0.017(4) -0.015(4) C21A 0.054(5) 0.050(4) 0.048(4) 0.013(3) 0.010(4) -0.004(3) C22A 0.031(3) 0.038(3) 0.048(4) 0.011(3) 0.001(3) -0.002(3) C23A 0.017(3) 0.028(3) 0.038(3) 0.002(2) 0.000(3) 0.000(2) C24A 0.026(3) 0.041(3) 0.033(3) 0.009(3) 0.001(3) -0.001(3) O1B 0.024(2) 0.034(2) 0.048(3) 0.0019(18) 0.000(2) 0.0008(17) O2B 0.0160(19) 0.038(2) 0.041(3) 0.0013(18) 0.0011(18) 0.0034(16) O3B 0.023(2) 0.031(2) 0.043(2) 0.0042(17) 0.0082(19) 0.0068(16) O4B 0.020(2) 0.030(2) 0.045(2) -0.0049(17) -0.0102(19) 0.0009(16) O5B 0.028(2) 0.037(2) 0.072(3) -0.001(2) 0.005(2) -0.0068(19) O6B 0.029(2) 0.041(2) 0.042(2) -0.0062(19) 0.008(2) 0.0007(19) N1B 0.020(2) 0.033(2) 0.030(3) -0.001(2) -0.001(2) 0.005(2) C1B 0.057(5) 0.051(4) 0.066(5) 0.006(4) 0.035(4) 0.002(3) C2B 0.035(4) 0.048(4) 0.090(6) 0.017(4) -0.013(4) -0.009(3) C3B 0.024(3) 0.033(3) 0.049(4) 0.008(3) 0.008(3) -0.004(2) C4B 0.027(3) 0.036(3) 0.035(3) 0.005(3) 0.000(3) -0.003(3) C5B 0.024(3) 0.035(3) 0.029(3) -0.003(2) 0.003(3) -0.003(3) C6B 0.020(3) 0.041(3) 0.030(3) 0.003(3) -0.005(3) 0.000(2) C7B 0.016(3) 0.033(3) 0.034(3) 0.001(2) 0.000(3) 0.000(2) C8B 0.036(4) 0.037(3) 0.068(5) -0.011(3) -0.006(4) 0.003(3) C9B 0.024(3) 0.029(3) 0.048(4) -0.008(3) -0.010(3) 0.000(3) C10B 0.046(4) 0.037(3) 0.048(4) 0.003(3) 0.011(4) 0.001(3) C11B 0.023(4) 0.037(4) 0.110(7) 0.016(4) 0.015(4) 0.002(3) C12B 0.045(5) 0.034(4) 0.105(7) 0.002(4) -0.032(5) -0.008(3) C13B 0.069(5) 0.039(4) 0.055(5) -0.009(3) -0.026(4) 0.003(4) C14B 0.048(4) 0.027(3) 0.042(4) -0.002(3) -0.002(3) -0.006(3) C15B 0.019(3) 0.035(3) 0.031(3) -0.003(2) -0.004(3) 0.004(2) C16B 0.025(3) 0.033(3) 0.033(3) 0.000(3) 0.001(3) -0.001(3) C17B 0.029(3) 0.027(3) 0.043(4) 0.001(3) -0.001(3) 0.001(2) C18B 0.039(4) 0.045(4) 0.039(4) 0.017(3) -0.004(3) 0.005(3) C19B 0.061(5) 0.043(4) 0.049(4) 0.012(3) -0.007(4) 0.005(3) C20B 0.048(5) 0.055(4) 0.073(6) 0.005(4) -0.022(5) 0.013(4) C21B 0.035(4) 0.063(4) 0.088(6) -0.020(4) -0.005(4) 0.018(3) C22B 0.035(4) 0.053(4) 0.048(4) -0.004(3) 0.000(4) 0.011(3) C23B 0.024(3) 0.042(3) 0.038(4) 0.000(3) 0.005(3) 0.004(3) C24B 0.020(3) 0.039(3) 0.040(4) 0.008(3) 0.001(3) 0.001(3) O1W 0.042(3) 0.053(3) 0.127(5) -0.008(3) -0.015(3) 0.007(2) O2W 0.061(3) 0.073(3) 0.086(4) 0.015(3) 0.000(3) -0.007(3) O3W 0.028(2) 0.055(2) 0.049(3) 0.002(2) 0.001(2) -0.006(2) O4W 0.057(3) 0.057(3) 0.066(3) 0.009(2) 0.005(3) 0.015(2) O5W 0.063(3) 0.059(3) 0.093(4) 0.010(3) -0.011(3) 0.016(3) _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 O1A C4A 1.418(6) . ? O1A C3A 1.432(6) . ? O2A C5A 1.434(6) . ? O2A C3A 1.438(6) . ? O3A C4A 1.414(6) . ? O3A C7A 1.443(6) . ? O4A C6A 1.429(6) . ? O4A C8A 1.430(6) . ? O5A C24A 1.239(6) . ? O6A C24A 1.257(6) . ? N1A C16A 1.492(7) . ? N1A C15A 1.510(6) . ? N1A H1AX 0.968(11) . ? N1A H1AY 0.967(11) . ? C1A C3A 1.513(8) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A C3A 1.492(8) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C4A C5A 1.544(7) . ? C4A H4A 1.0000 . ? C5A C6A 1.518(7) . ? C5A H5A 1.0000 . ? C6A C7A 1.537(7) . ? C6A H6A 1.0000 . ? C7A C15A 1.536(7) . ? C7A H7A 1.0000 . ? C8A C9A 1.511(8) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.367(7) . ? C9A C14A 1.397(8) . ? C10A C11A 1.388(8) . ? C10A H10A 0.9500 . ? C11A C12A 1.375(9) . ? C11A H11A 0.9500 . ? C12A C13A 1.384(9) . ? C12A H12A 0.9500 . ? C13A C14A 1.398(8) . ? C13A H13A 0.9500 . ? C14A H14A 0.9500 . ? C15A C23A 1.519(7) . ? C15A H15A 1.0000 . ? C16A C17A 1.509(8) . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C17A C22A 1.388(8) . ? C17A C18A 1.389(8) . ? C18A C19A 1.377(9) . ? C18A H18A 0.9500 . ? C19A C20A 1.365(10) . ? C19A H19A 0.9500 . ? C20A C21A 1.388(9) . ? C20A H20A 0.9500 . ? C21A C22A 1.378(8) . ? C21A H21A 0.9500 . ? C22A H22A 0.9500 . ? C23A C24A 1.526(7) . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? O1B C3B 1.410(6) . ? O1B C4B 1.426(6) . ? O2B C5B 1.437(6) . ? O2B C3B 1.451(6) . ? O3B C4B 1.415(6) . ? O3B C7B 1.446(6) . ? O4B C6B 1.426(6) . ? O4B C8B 1.435(6) . ? O5B C24B 1.252(6) . ? O6B C24B 1.250(6) . ? N1B C15B 1.499(6) . ? N1B C16B 1.508(6) . ? N1B H1BY 0.969(10) . ? N1B H1BX 0.971(11) . ? C1B C3B 1.505(8) . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C2B C3B 1.504(8) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C4B C5B 1.535(7) . ? C4B H4B 1.0000 . ? C5B C6B 1.533(7) . ? C5B H5B 1.0000 . ? C6B C7B 1.523(7) . ? C6B H6B 1.0000 . ? C7B C15B 1.512(7) . ? C7B H7B 1.0000 . ? C8B C9B 1.513(8) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.377(8) . ? C9B C14B 1.389(8) . ? C10B C11B 1.400(9) . ? C10B H10B 0.9500 . ? C11B C12B 1.384(10) . ? C11B H11B 0.9500 . ? C12B C13B 1.354(10) . ? C12B H12B 0.9500 . ? C13B C14B 1.371(9) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C15B C23B 1.548(7) . ? C15B H15B 1.0000 . ? C16B C17B 1.516(7) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B C18B 1.379(8) . ? C17B C22B 1.389(8) . ? C18B C19B 1.386(8) . ? C18B H18B 0.9500 . ? C19B C20B 1.356(9) . ? C19B H19B 0.9500 . ? C20B C21B 1.364(10) . ? C20B H20B 0.9500 . ? C21B C22B 1.401(9) . ? C21B H21B 0.9500 . ? C22B H22B 0.9500 . ? C23B C24B 1.555(7) . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? 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 C4A O1A C3A 108.9(4) . . ? C5A O2A C3A 108.7(4) . . ? C4A O3A C7A 105.7(4) . . ? C6A O4A C8A 111.0(4) . . ? C16A N1A C15A 118.3(4) . . ? C16A N1A H1AX 104(3) . . ? C15A N1A H1AX 110(3) . . ? C16A N1A H1AY 111(3) . . ? C15A N1A H1AY 100(3) . . ? H1AX N1A H1AY 113(4) . . ? C3A C1A H1A1 109.5 . . ? C3A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C3A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C3A C2A H2A1 109.5 . . ? C3A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C3A C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? O1A C3A O2A 104.7(4) . . ? O1A C3A C2A 109.1(5) . . ? O2A C3A C2A 107.8(4) . . ? O1A C3A C1A 109.4(4) . . ? O2A C3A C1A 111.3(4) . . ? C2A C3A C1A 114.0(5) . . ? O3A C4A O1A 109.8(4) . . ? O3A C4A C5A 107.0(4) . . ? O1A C4A C5A 105.6(4) . . ? O3A C4A H4A 111.4 . . ? O1A C4A H4A 111.4 . . ? C5A C4A H4A 111.4 . . ? O2A C5A C6A 109.4(4) . . ? O2A C5A C4A 103.9(4) . . ? C6A C5A C4A 104.1(4) . . ? O2A C5A H5A 112.9 . . ? C6A C5A H5A 112.9 . . ? C4A C5A H5A 112.9 . . ? O4A C6A C5A 110.7(4) . . ? O4A C6A C7A 109.4(4) . . ? C5A C6A C7A 101.0(4) . . ? O4A C6A H6A 111.7 . . ? C5A C6A H6A 111.7 . . ? C7A C6A H6A 111.7 . . ? O3A C7A C15A 110.3(4) . . ? O3A C7A C6A 103.0(4) . . ? C15A C7A C6A 115.6(4) . . ? O3A C7A H7A 109.3 . . ? C15A C7A H7A 109.3 . . ? C6A C7A H7A 109.3 . . ? O4A C8A C9A 108.9(4) . . ? O4A C8A H8A1 109.9 . . ? C9A C8A H8A1 109.9 . . ? O4A C8A H8A2 109.9 . . ? C9A C8A H8A2 109.9 . . ? H8A1 C8A H8A2 108.3 . . ? C10A C9A C14A 119.8(5) . . ? C10A C9A C8A 122.3(6) . . ? C14A C9A C8A 117.9(5) . . ? C9A C10A C11A 121.5(6) . . ? C9A C10A H10A 119.3 . . ? C11A C10A H10A 119.3 . . ? C12A C11A C10A 119.1(6) . . ? C12A C11A H11A 120.4 . . ? C10A C11A H11A 120.4 . . ? C11A C12A C13A 120.5(6) . . ? C11A C12A H12A 119.8 . . ? C13A C12A H12A 119.8 . . ? C12A C13A C14A 120.2(6) . . ? C12A C13A H13A 119.9 . . ? C14A C13A H13A 119.9 . . ? C9A C14A C13A 118.9(6) . . ? C9A C14A H14A 120.5 . . ? C13A C14A H14A 120.5 . . ? N1A C15A C23A 107.9(4) . . ? N1A C15A C7A 108.8(4) . . ? C23A C15A C7A 111.2(4) . . ? N1A C15A H15A 109.6 . . ? C23A C15A H15A 109.6 . . ? C7A C15A H15A 109.6 . . ? N1A C16A C17A 112.6(4) . . ? N1A C16A H16A 109.1 . . ? C17A C16A H16A 109.1 . . ? N1A C16A H16B 109.1 . . ? C17A C16A H16B 109.1 . . ? H16A C16A H16B 107.8 . . ? C22A C17A C18A 119.1(6) . . ? C22A C17A C16A 120.9(5) . . ? C18A C17A C16A 120.1(6) . . ? C19A C18A C17A 120.1(6) . . ? C19A C18A H18A 119.9 . . ? C17A C18A H18A 119.9 . . ? C20A C19A C18A 120.8(7) . . ? C20A C19A H19A 119.6 . . ? C18A C19A H19A 119.6 . . ? C19A C20A C21A 119.7(7) . . ? C19A C20A H20A 120.2 . . ? C21A C20A H20A 120.2 . . ? C22A C21A C20A 120.0(6) . . ? C22A C21A H21A 120.0 . . ? C20A C21A H21A 120.0 . . ? C21A C22A C17A 120.3(6) . . ? C21A C22A H22A 119.8 . . ? C17A C22A H22A 119.8 . . ? C15A C23A C24A 115.1(4) . . ? C15A C23A H23A 108.5 . . ? C24A C23A H23A 108.5 . . ? C15A C23A H23B 108.5 . . ? C24A C23A H23B 108.5 . . ? H23A C23A H23B 107.5 . . ? O5A C24A O6A 125.2(5) . . ? O5A C24A C23A 118.8(5) . . ? O6A C24A C23A 115.9(5) . . ? C3B O1B C4B 109.1(4) . . ? C5B O2B C3B 106.6(4) . . ? C4B O3B C7B 107.9(4) . . ? C6B O4B C8B 111.0(4) . . ? C15B N1B C16B 117.2(4) . . ? C15B N1B H1BY 113(3) . . ? C16B N1B H1BY 106(3) . . ? C15B N1B H1BX 108(3) . . ? C16B N1B H1BX 109(3) . . ? H1BY N1B H1BX 103(4) . . ? C3B C1B H1B1 109.5 . . ? C3B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C3B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? C3B C2B H2B1 109.5 . . ? C3B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C3B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? O1B C3B O2B 104.9(4) . . ? O1B C3B C2B 109.4(5) . . ? O2B C3B C2B 107.4(4) . . ? O1B C3B C1B 110.7(5) . . ? O2B C3B C1B 109.9(5) . . ? C2B C3B C1B 114.2(5) . . ? O3B C4B O1B 109.4(4) . . ? O3B C4B C5B 107.1(4) . . ? O1B C4B C5B 105.1(4) . . ? O3B C4B H4B 111.6 . . ? O1B C4B H4B 111.6 . . ? C5B C4B H4B 111.6 . . ? O2B C5B C6B 109.4(4) . . ? O2B C5B C4B 104.3(4) . . ? C6B C5B C4B 104.2(4) . . ? O2B C5B H5B 112.7 . . ? C6B C5B H5B 112.7 . . ? C4B C5B H5B 112.7 . . ? O4B C6B C7B 108.5(4) . . ? O4B C6B C5B 109.9(4) . . ? C7B C6B C5B 101.5(4) . . ? O4B C6B H6B 112.1 . . ? C7B C6B H6B 112.1 . . ? C5B C6B H6B 112.1 . . ? O3B C7B C15B 108.6(4) . . ? O3B C7B C6B 103.7(4) . . ? C15B C7B C6B 116.4(4) . . ? O3B C7B H7B 109.3 . . ? C15B C7B H7B 109.3 . . ? C6B C7B H7B 109.3 . . ? O4B C8B C9B 108.9(5) . . ? O4B C8B H8B1 109.9 . . ? C9B C8B H8B1 109.9 . . ? O4B C8B H8B2 109.9 . . ? C9B C8B H8B2 109.9 . . ? H8B1 C8B H8B2 108.3 . . ? C10B C9B C14B 119.5(6) . . ? C10B C9B C8B 119.3(6) . . ? C14B C9B C8B 121.1(6) . . ? C9B C10B C11B 120.0(6) . . ? C9B C10B H10B 120.0 . . ? C11B C10B H10B 120.0 . . ? C12B C11B C10B 118.9(7) . . ? C12B C11B H11B 120.5 . . ? C10B C11B H11B 120.5 . . ? C13B C12B C11B 120.8(7) . . ? C13B C12B H12B 119.6 . . ? C11B C12B H12B 119.6 . . ? C12B C13B C14B 120.6(7) . . ? C12B C13B H13B 119.7 . . ? C14B C13B H13B 119.7 . . ? C13B C14B C9B 120.1(6) . . ? C13B C14B H14B 119.9 . . ? C9B C14B H14B 119.9 . . ? N1B C15B C7B 111.3(4) . . ? N1B C15B C23B 107.2(4) . . ? C7B C15B C23B 111.7(4) . . ? N1B C15B H15B 108.9 . . ? C7B C15B H15B 108.9 . . ? C23B C15B H15B 108.9 . . ? N1B C16B C17B 113.3(4) . . ? N1B C16B H16C 108.9 . . ? C17B C16B H16C 108.9 . . ? N1B C16B H16D 108.9 . . ? C17B C16B H16D 108.9 . . ? H16C C16B H16D 107.7 . . ? C18B C17B C22B 120.0(5) . . ? C18B C17B C16B 120.9(5) . . ? C22B C17B C16B 119.1(5) . . ? C17B C18B C19B 119.4(6) . . ? C17B C18B H18B 120.3 . . ? C19B C18B H18B 120.3 . . ? C20B C19B C18B 120.9(6) . . ? C20B C19B H19B 119.5 . . ? C18B C19B H19B 119.5 . . ? C19B C20B C21B 120.5(7) . . ? C19B C20B H20B 119.8 . . ? C21B C20B H20B 119.8 . . ? C20B C21B C22B 120.0(7) . . ? C20B C21B H21B 120.0 . . ? C22B C21B H21B 120.0 . . ? C17B C22B C21B 119.1(6) . . ? C17B C22B H22B 120.4 . . ? C21B C22B H22B 120.4 . . ? C15B C23B C24B 113.2(4) . . ? C15B C23B H23C 108.9 . . ? C24B C23B H23C 108.9 . . ? C15B C23B H23D 108.9 . . ? C24B C23B H23D 108.9 . . ? H23C C23B H23D 107.8 . . ? O6B C24B O5B 126.2(5) . . ? O6B C24B C23B 116.5(5) . . ? O5B C24B C23B 117.2(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 C4A O1A C3A O2A 27.4(5) . . . . ? C4A O1A C3A C2A 142.6(5) . . . . ? C4A O1A C3A C1A -92.0(5) . . . . ? C5A O2A C3A O1A -28.7(5) . . . . ? C5A O2A C3A C2A -144.8(5) . . . . ? C5A O2A C3A C1A 89.4(5) . . . . ? C7A O3A C4A O1A 86.9(4) . . . . ? C7A O3A C4A C5A -27.3(5) . . . . ? C3A O1A C4A O3A -130.8(4) . . . . ? C3A O1A C4A C5A -15.8(5) . . . . ? C3A O2A C5A C6A 129.5(4) . . . . ? C3A O2A C5A C4A 18.8(5) . . . . ? O3A C4A C5A O2A 115.1(4) . . . . ? O1A C4A C5A O2A -1.9(5) . . . . ? O3A C4A C5A C6A 0.5(5) . . . . ? O1A C4A C5A C6A -116.4(4) . . . . ? C8A O4A C6A C5A -88.6(5) . . . . ? C8A O4A C6A C7A 160.8(4) . . . . ? O2A C5A C6A O4A 157.6(4) . . . . ? C4A C5A C6A O4A -91.8(5) . . . . ? O2A C5A C6A C7A -86.5(4) . . . . ? C4A C5A C6A C7A 24.1(5) . . . . ? C4A O3A C7A C15A 167.0(4) . . . . ? C4A O3A C7A C6A 43.1(4) . . . . ? O4A C6A C7A O3A 75.8(5) . . . . ? C5A C6A C7A O3A -41.0(5) . . . . ? O4A C6A C7A C15A -44.5(6) . . . . ? C5A C6A C7A C15A -161.3(4) . . . . ? C6A O4A C8A C9A -177.7(5) . . . . ? O4A C8A C9A C10A -93.4(6) . . . . ? O4A C8A C9A C14A 87.1(6) . . . . ? C14A C9A C10A C11A -0.6(8) . . . . ? C8A C9A C10A C11A 179.9(5) . . . . ? C9A C10A C11A C12A 0.9(9) . . . . ? C10A C11A C12A C13A -0.9(9) . . . . ? C11A C12A C13A C14A 0.5(9) . . . . ? C10A C9A C14A C13A 0.1(8) . . . . ? C8A C9A C14A C13A 179.7(5) . . . . ? C12A C13A C14A C9A -0.1(8) . . . . ? C16A N1A C15A C23A 166.6(4) . . . . ? C16A N1A C15A C7A -72.6(6) . . . . ? O3A C7A C15A N1A 76.6(5) . . . . ? C6A C7A C15A N1A -167.2(4) . . . . ? O3A C7A C15A C23A -164.6(4) . . . . ? C6A C7A C15A C23A -48.4(6) . . . . ? C15A N1A C16A C17A -65.2(6) . . . . ? N1A C16A C17A C22A 103.4(6) . . . . ? N1A C16A C17A C18A -76.3(7) . . . . ? C22A C17A C18A C19A -0.1(9) . . . . ? C16A C17A C18A C19A 179.6(6) . . . . ? C17A C18A C19A C20A 0.1(11) . . . . ? C18A C19A C20A C21A 0.5(11) . . . . ? C19A C20A C21A C22A -1.2(10) . . . . ? C20A C21A C22A C17A 1.2(9) . . . . ? C18A C17A C22A C21A -0.6(9) . . . . ? C16A C17A C22A C21A 179.7(5) . . . . ? N1A C15A C23A C24A -57.3(6) . . . . ? C7A C15A C23A C24A -176.6(4) . . . . ? C15A C23A C24A O5A 30.2(7) . . . . ? C15A C23A C24A O6A -152.2(5) . . . . ? C4B O1B C3B O2B 28.5(5) . . . . ? C4B O1B C3B C2B 143.4(5) . . . . ? C4B O1B C3B C1B -90.0(5) . . . . ? C5B O2B C3B O1B -32.4(5) . . . . ? C5B O2B C3B C2B -148.7(4) . . . . ? C5B O2B C3B C1B 86.6(5) . . . . ? C7B O3B C4B O1B 93.1(5) . . . . ? C7B O3B C4B C5B -20.3(5) . . . . ? C3B O1B C4B O3B -128.5(4) . . . . ? C3B O1B C4B C5B -13.8(6) . . . . ? C3B O2B C5B C6B 134.5(4) . . . . ? C3B O2B C5B C4B 23.4(5) . . . . ? O3B C4B C5B O2B 110.0(4) . . . . ? O1B C4B C5B O2B -6.3(6) . . . . ? O3B C4B C5B C6B -4.8(5) . . . . ? O1B C4B C5B C6B -121.0(4) . . . . ? C8B O4B C6B C7B 160.3(5) . . . . ? C8B O4B C6B C5B -89.6(5) . . . . ? O2B C5B C6B O4B 160.3(4) . . . . ? C4B C5B C6B O4B -88.6(5) . . . . ? O2B C5B C6B C7B -85.0(5) . . . . ? C4B C5B C6B C7B 26.1(5) . . . . ? C4B O3B C7B C15B 161.9(4) . . . . ? C4B O3B C7B C6B 37.6(5) . . . . ? O4B C6B C7B O3B 77.2(5) . . . . ? C5B C6B C7B O3B -38.6(5) . . . . ? O4B C6B C7B C15B -41.9(6) . . . . ? C5B C6B C7B C15B -157.6(4) . . . . ? C6B O4B C8B C9B -175.6(5) . . . . ? O4B C8B C9B C10B 82.0(7) . . . . ? O4B C8B C9B C14B -98.6(6) . . . . ? C14B C9B C10B C11B -0.5(9) . . . . ? C8B C9B C10B C11B 178.9(5) . . . . ? C9B C10B C11B C12B -0.1(9) . . . . ? C10B C11B C12B C13B 0.5(9) . . . . ? C11B C12B C13B C14B -0.3(10) . . . . ? C12B C13B C14B C9B -0.3(9) . . . . ? C10B C9B C14B C13B 0.7(9) . . . . ? C8B C9B C14B C13B -178.7(5) . . . . ? C16B N1B C15B C7B -68.8(5) . . . . ? C16B N1B C15B C23B 168.8(4) . . . . ? O3B C7B C15B N1B 74.4(5) . . . . ? C6B C7B C15B N1B -169.2(4) . . . . ? O3B C7B C15B C23B -165.9(4) . . . . ? C6B C7B C15B C23B -49.5(6) . . . . ? C15B N1B C16B C17B -67.3(6) . . . . ? N1B C16B C17B C18B 105.9(6) . . . . ? N1B C16B C17B C22B -76.7(6) . . . . ? C22B C17B C18B C19B 0.6(9) . . . . ? C16B C17B C18B C19B 178.0(5) . . . . ? C17B C18B C19B C20B -0.1(9) . . . . ? C18B C19B C20B C21B -0.4(10) . . . . ? C19B C20B C21B C22B 0.3(10) . . . . ? C18B C17B C22B C21B -0.6(9) . . . . ? C16B C17B C22B C21B -178.1(5) . . . . ? C20B C21B C22B C17B 0.1(10) . . . . ? N1B C15B C23B C24B -68.7(6) . . . . ? C7B C15B C23B C24B 169.1(5) . . . . ? C15B C23B C24B O6B 44.7(7) . . . . ? C15B C23B C24B O5B -132.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.78 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.331 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 888184'