# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_compound_3 _database_code_depnum_ccdc_archive 'CCDC 766937' #data_8596 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H38 N2 O9' _chemical_formula_weight 750.77 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 0.0016 '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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4208(6) _cell_length_b 10.3302(6) _cell_length_c 34.5404(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.195(2) _cell_angle_gamma 90.00 _cell_volume 3708.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2813 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 21.81 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21057 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6533 _reflns_number_gt 4752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+4.4746P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6533 _refine_ls_number_parameters 514 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1796 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 64.965 _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 1.518(15) 0.926(16) 0.643(4) 0.06(5) Uani 1 1 d . . . H1 H 1.5659 0.9390 0.6248 0.083 Uiso 1 1 calc R . . O2 O 1.54(2) 0.722(18) 0.625(6) 0.10(8) Uani 1 1 d . . . O3 O 1.01(3) 0.401(16) 0.543(5) 0.10(8) Uani 1 1 d . . . H3 H 1.0133 0.4019 0.5193 0.145 Uiso 1 1 calc R . . O4 O 0.99(2) 0.614(16) 0.533(4) 0.09(8) Uani 1 1 d . . . O5 O 1.03(4) 0.89(3) 0.939(7) 0.17(16) Uani 1 1 d . . . O6 O 0.85(3) 0.97(3) 0.923(6) 0.12(10) Uani 1 1 d . . . H6 H 0.8546 0.9939 0.9463 0.179 Uiso 1 1 calc R . . O7 O 0.492(13) 0.492(15) 0.859(4) 0.05(4) Uani 1 1 d . . . H7 H 0.4318 0.4871 0.8737 0.068 Uiso 1 1 calc R . . O8 O 0.364(14) 0.636(15) 0.828(5) 0.06(5) Uani 1 1 d . . . C1 C 1.082(17) 0.671(18) 0.742(5) 0.03(4) Uani 1 1 d . . . H1A H 1.1136 0.6233 0.7656 0.033 Uiso 1 1 calc R . . C2 C 0.969(17) 0.592(18) 0.720(5) 0.03(4) Uani 1 1 d . . . H2 H 0.9559 0.5084 0.7330 0.034 Uiso 1 1 calc R . . C3 C 0.871(17) 0.695(18) 0.733(5) 0.03(4) Uani 1 1 d . . . H3A H 0.8341 0.7429 0.7096 0.034 Uiso 1 1 calc R . . C4 C 0.985(16) 0.776(18) 0.753(5) 0.03(4) Uani 1 1 d . . . H4 H 0.9985 0.8549 0.7378 0.032 Uiso 1 1 calc R . . C5 C 1.49(2) 0.80(2) 0.644(6) 0.04(5) Uani 1 1 d . . . C6 C 1.391(17) 0.77(2) 0.671(5) 0.03(5) Uani 1 1 d . . . C7 C 1.325(18) 0.87(2) 0.689(5) 0.04(5) Uani 1 1 d . . . H7A H 1.3464 0.9559 0.6856 0.042 Uiso 1 1 calc R . . C8 C 1.227(18) 0.837(19) 0.713(5) 0.03(4) Uani 1 1 d . . . H8 H 1.1833 0.9032 0.7252 0.040 Uiso 1 1 calc R . . C9 C 1.194(16) 0.709(18) 0.719(5) 0.03(4) Uani 1 1 d . . . C10 C 1.264(18) 0.613(19) 0.702(5) 0.03(5) Uani 1 1 d . . . H10 H 1.2450 0.5256 0.7067 0.041 Uiso 1 1 calc R . . C11 C 1.360(18) 0.64(2) 0.678(5) 0.04(5) Uani 1 1 d . . . H11 H 1.4058 0.5770 0.6668 0.045 Uiso 1 1 calc R . . C12 C 1.00(3) 0.52(2) 0.555(7) 0.07(8) Uani 1 1 d . . . C13 C 0.99(2) 0.54(2) 0.597(6) 0.04(5) Uani 1 1 d . . . C14 C 0.98(2) 0.659(19) 0.613(5) 0.04(5) Uani 1 1 d . . . H14 H 0.9764 0.7303 0.5957 0.045 Uiso 1 1 calc R . . C15 C 0.971(18) 0.677(19) 0.651(5) 0.03(4) Uani 1 1 d . . . H15 H 0.9616 0.7616 0.6611 0.039 Uiso 1 1 calc R . . C16 C 0.975(17) 0.573(18) 0.677(5) 0.03(4) Uani 1 1 d . . . C17 C 0.99(2) 0.450(19) 0.662(5) 0.04(5) Uani 1 1 d . . . H17 H 0.9933 0.3783 0.6785 0.046 Uiso 1 1 calc R . . C18 C 1.00(2) 0.43(2) 0.623(6) 0.05(6) Uani 1 1 d . . . H18 H 1.0056 0.3467 0.6130 0.057 Uiso 1 1 calc R . . C19 C 0.95(4) 0.92(3) 0.914(9) 0.08(9) Uani 1 1 d . . . C20 C 0.96(2) 0.88(2) 0.873(6) 0.05(6) Uani 1 1 d . . . C21 C 1.06(3) 0.81(3) 0.862(7) 0.07(8) Uani 1 1 d . . . H21 H 1.1274 0.7909 0.8807 0.078 Uiso 1 1 calc R . . C22 C 1.07(2) 0.78(2) 0.823(6) 0.05(6) Uani 1 1 d . . . H22 H 1.1457 0.7330 0.8165 0.055 Uiso 1 1 calc R . . C23 C 0.979(17) 0.813(17) 0.795(5) 0.03(4) Uani 1 1 d . . . C24 C 0.876(18) 0.886(19) 0.806(6) 0.04(5) Uani 1 1 d . . . H24 H 0.8122 0.9122 0.7875 0.044 Uiso 1 1 calc R . . C25 C 0.87(2) 0.92(2) 0.844(6) 0.04(5) Uani 1 1 d . . . H25 H 0.7941 0.9700 0.8509 0.053 Uiso 1 1 calc R . . C26 C 0.464(18) 0.577(19) 0.832(6) 0.04(5) Uani 1 1 d . . . C27 C 0.568(17) 0.594(18) 0.805(5) 0.03(4) Uani 1 1 d . . . C28 C 0.689(17) 0.541(18) 0.812(5) 0.03(4) Uani 1 1 d . . . H28 H 0.7055 0.4850 0.8333 0.034 Uiso 1 1 calc R . . C29 C 0.787(17) 0.571(18) 0.789(5) 0.03(4) Uani 1 1 d . . . H29 H 0.8694 0.5353 0.7942 0.035 Uiso 1 1 calc R . . C30 C 0.765(17) 0.652(17) 0.757(5) 0.03(4) Uani 1 1 d . . . C31 C 0.642(17) 0.699(18) 0.749(5) 0.03(4) Uani 1 1 d . . . H31 H 0.6241 0.7517 0.7265 0.036 Uiso 1 1 calc R . . C32 C 0.544(17) 0.672(19) 0.772(5) 0.03(4) Uani 1 1 d . . . H32 H 0.4610 0.7055 0.7662 0.039 Uiso 1 1 calc R . . C1S C 0.83(12) 0.90(5) 1.02(3) 0.2(5) Uani 0.7(8) 1 d PDU A 3 H1SA H 0.9159 0.8602 1.0143 0.304 Uiso 0.7(8) 1 calc PR A 3 H1SB H 0.7666 0.8404 1.0040 0.304 Uiso 0.7(8) 1 calc PR A 3 H1SC H 0.8156 0.9082 1.0435 0.304 Uiso 0.7(8) 1 calc PR A 3 O1S O 0.82(6) 1.02(5) 0.997(11) 0.1(2) Uani 0.7(8) 1 d PDU A 3 H1S H 0.8517 1.0797 1.0126 0.190 Uiso 0.7(8) 1 calc PRD A 3 C2S C 0.75(10) 0.99(14) 1.01(5) 0.1(6) Uiso 0.3(8) 1 d PD A 4 H2SA H 0.7485 0.9939 1.0419 0.211 Uiso 0.3(8) 1 calc PR A 4 H2SB H 0.6930 0.9233 1.0036 0.211 Uiso 0.3(8) 1 calc PR A 4 H2SC H 0.7232 1.0736 1.0029 0.211 Uiso 0.3(8) 1 calc PR A 4 O2S O 0.88(11) 0.96(14) 1.00(5) 0.2(7) Uiso 0.3(8) 1 d PD A 4 H2S H 0.9296 1.0222 1.0120 0.274 Uiso 0.3(8) 1 calc PRD A 4 N1 N 1.688(16) 0.976(18) 0.591(5) 0.04(4) Uani 1 1 d . . . C33 C 1.73(2) 1.09(2) 0.584(6) 0.05(5) Uani 1 1 d . . . H33 H 1.6969 1.1640 0.5974 0.054 Uiso 1 1 calc R . . C34 C 1.82(2) 1.12(2) 0.557(6) 0.04(5) Uani 1 1 d . . . H34 H 1.8452 1.2046 0.5531 0.051 Uiso 1 1 calc R . . C35 C 1.871(18) 1.02(2) 0.537(5) 0.03(5) Uani 1 1 d . . . C36 C 1.826(19) 0.90(2) 0.545(6) 0.04(5) Uani 1 1 d . . . H36 H 1.8564 0.8230 0.5315 0.047 Uiso 1 1 calc R . . C37 C 1.74(2) 0.88(2) 0.572(6) 0.04(5) Uani 1 1 d . . . H37 H 1.7072 0.7946 0.5766 0.052 Uiso 1 1 calc R . . C38 C 1.967(18) 1.04(2) 0.509(5) 0.04(5) Uani 1 1 d . . . H38 H 1.9841 1.1307 0.5041 0.043 Uiso 1 1 calc R . . N2 N 0.31(3) 0.45(4) 0.908(10) 0.03(10) Uiso 0.50 1 d PD B 1 C39 C 0.26(4) 0.35(5) 0.923(13) 0.04(12) Uiso 0.50 1 d PD B 1 H39 H 0.2931 0.2657 0.9147 0.053 Uiso 0.50 1 calc PR B 1 C40 C 0.17(4) 0.35(5) 0.949(12) 0.04(11) Uiso 0.50 1 d PD B 1 H40 H 0.1388 0.2710 0.9589 0.052 Uiso 0.50 1 calc PR B 1 C41 C 0.12(4) 0.47(4) 0.962(12) 0.03(9) Uiso 0.50 1 d PD B 1 C42 C 0.17(4) 0.58(5) 0.947(12) 0.04(11) Uiso 0.50 1 d PD B 1 H42 H 0.1439 0.6604 0.9547 0.052 Uiso 0.50 1 calc PR B 1 C43 C 0.26(4) 0.57(5) 0.919(12) 0.04(11) Uiso 0.50 1 d PD B 1 H43 H 0.2949 0.6432 0.9085 0.047 Uiso 0.50 1 calc PR B 1 C44 C 0.03(5) 0.46(6) 0.991(15) 0.06(13) Uiso 0.50 1 d PD . 1 H44 H 0.0009 0.3760 0.9963 0.071 Uiso 0.50 1 calc PR . 1 N2X N 0.31(4) 0.50(4) 0.910(11) 0.04(11) Uiso 0.50 1 d PD C 2 C39X C 0.24(4) 0.40(5) 0.920(14) 0.05(13) Uiso 0.50 1 d PD C 2 H39X H 0.2563 0.3176 0.9089 0.057 Uiso 0.50 1 calc PR C 2 C40X C 0.15(4) 0.41(5) 0.946(13) 0.05(12) Uiso 0.50 1 d PD C 2 H40X H 0.0980 0.3417 0.9531 0.060 Uiso 0.50 1 calc PR C 2 C41X C 0.13(4) 0.53(4) 0.962(12) 0.04(10) Uiso 0.50 1 d PD C 2 C42X C 0.20(4) 0.64(5) 0.951(13) 0.05(13) Uiso 0.50 1 d PD C 2 H42X H 0.1870 0.7188 0.9609 0.063 Uiso 0.50 1 calc PR C 2 C43X C 0.29(5) 0.62(5) 0.925(14) 0.05(13) Uiso 0.50 1 d PD C 2 H43X H 0.3432 0.6856 0.9185 0.061 Uiso 0.50 1 calc PR C 2 C44X C 0.03(4) 0.55(5) 0.990(12) 0.04(9) Uiso 0.50 1 d PD . 2 H44X H 0.0054 0.6350 0.9948 0.045 Uiso 0.50 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.05(10) 0.07(12) 0.05(10) -0.02(8) 0.03(7) -0.03(8) O2 0.12(17) 0.06(12) 0.12(17) 0.03(11) 0.10(15) 0.03(11) O3 0.2(3) 0.04(10) 0.03(9) -0.01(7) 0.03(13) 0.00(13) O4 0.2(2) 0.04(10) 0.03(8) 0.00(7) 0.03(11) 0.00(12) O5 0.3(4) 0.2(3) 0.05(14) -0.05(17) 0.0(2) 0.1(3) O6 0.1(2) 0.2(3) 0.06(14) -0.05(16) 0.03(14) 0.01(19) O7 0.04(8) 0.06(10) 0.04(9) 0.00(7) 0.03(7) 0.00(7) O8 0.04(9) 0.06(10) 0.08(12) 0.01(9) 0.03(8) 0.01(8) C1 0.03(10) 0.03(10) 0.02(9) 0.00(7) 0.01(7) 0.01(8) C2 0.03(10) 0.03(10) 0.03(10) 0.00(8) 0.01(7) 0.00(8) C3 0.03(10) 0.04(11) 0.02(9) 0.00(8) 0.01(7) 0.00(8) C4 0.03(9) 0.03(10) 0.03(10) 0.01(8) 0.01(7) 0.00(8) C5 0.04(12) 0.06(15) 0.03(12) 0.01(10) 0.01(9) 0.01(11) C6 0.02(10) 0.05(13) 0.03(10) 0.00(9) 0.01(8) 0.00(9) C7 0.03(11) 0.04(12) 0.03(10) -0.01(9) 0.01(8) -0.01(9) C8 0.03(10) 0.04(12) 0.03(10) -0.01(8) 0.01(8) 0.00(9) C9 0.02(9) 0.04(11) 0.02(9) 0.00(8) 0.00(7) 0.00(8) C10 0.03(11) 0.04(11) 0.03(11) 0.01(9) 0.01(8) 0.01(9) C11 0.03(11) 0.05(13) 0.03(11) 0.00(9) 0.01(9) 0.01(9) C12 0.1(3) 0.03(13) 0.03(13) 0.00(10) 0.02(14) 0.00(15) C13 0.07(15) 0.04(12) 0.02(10) 0.00(9) 0.01(10) 0.00(11) C14 0.06(13) 0.03(11) 0.02(10) 0.00(8) 0.01(9) 0.00(10) C15 0.04(11) 0.03(11) 0.02(10) 0.00(8) 0.01(8) 0.00(9) C16 0.03(9) 0.03(10) 0.02(9) 0.00(8) 0.01(7) 0.00(8) C17 0.06(13) 0.03(11) 0.03(11) 0.00(8) 0.02(9) 0.00(10) C18 0.08(17) 0.03(12) 0.03(12) -0.01(9) 0.02(11) 0.00(11) C19 0.1(3) 0.1(2) 0.04(17) -0.03(15) 0.01(18) 0.0(2) C20 0.07(17) 0.04(14) 0.03(12) -0.01(10) 0.01(12) 0.00(12) C21 0.1(2) 0.06(17) 0.04(13) -0.01(12) -0.02(13) 0.03(15) C22 0.05(13) 0.05(14) 0.04(12) -0.01(10) 0.00(10) 0.02(11) C23 0.03(9) 0.03(10) 0.03(10) 0.00(8) 0.01(8) 0.00(8) C24 0.03(10) 0.04(12) 0.04(12) -0.01(9) 0.01(9) 0.00(9) C25 0.04(12) 0.04(13) 0.05(14) -0.02(11) 0.02(10) -0.01(10) C26 0.03(10) 0.03(11) 0.05(12) -0.01(9) 0.02(9) 0.00(9) C27 0.03(10) 0.03(10) 0.03(10) -0.01(8) 0.01(8) -0.01(8) C28 0.03(10) 0.03(10) 0.02(10) 0.00(8) 0.01(7) 0.00(8) C29 0.02(9) 0.04(11) 0.03(10) 0.00(8) 0.01(7) 0.00(8) C30 0.03(9) 0.03(10) 0.02(9) -0.01(8) 0.01(7) 0.00(8) C31 0.03(10) 0.04(11) 0.02(10) 0.00(8) 0.00(7) 0.00(8) C32 0.02(9) 0.04(11) 0.04(11) -0.01(9) 0.00(8) 0.00(8) C1S 0.2(7) 0.2(7) 0.2(7) 0.0(5) 0.0(5) 0.0(6) O1S 0.1(4) 0.2(4) 0.1(2) 0.0(3) 0.0(2) 0.0(3) N1 0.03(9) 0.06(12) 0.03(9) 0.00(8) 0.01(7) 0.00(9) C33 0.04(12) 0.05(15) 0.04(12) 0.00(10) 0.02(10) 0.01(11) C34 0.05(12) 0.04(13) 0.04(12) 0.00(10) 0.01(10) 0.00(10) C35 0.03(10) 0.04(12) 0.03(10) 0.01(9) 0.01(8) 0.00(9) C36 0.04(11) 0.04(13) 0.04(12) 0.01(9) 0.01(9) 0.00(10) C37 0.04(12) 0.05(14) 0.04(12) 0.01(10) 0.01(9) -0.01(10) C38 0.04(11) 0.04(12) 0.03(11) 0.01(9) 0.01(8) 0.00(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 C5 1.3(3) . ? O2 C5 1.2(3) . ? O3 C12 1.3(3) . ? O4 C12 1.2(3) . ? O5 C19 1.2(4) . ? O6 C19 1.3(4) . ? O7 C26 1.3(2) . ? O8 C26 1.2(2) . ? C1 C9 1.5(2) . ? C1 C4 1.5(2) . ? C1 C2 1.6(3) . ? C2 C16 1.5(2) . ? C2 C3 1.6(2) . ? C3 C30 1.5(2) . ? C3 C4 1.6(3) . ? C4 C23 1.5(2) . ? C5 C6 1.5(3) . ? C6 C11 1.4(3) . ? C6 C7 1.4(3) . ? C7 C8 1.4(3) . ? C8 C9 1.4(3) . ? C9 C10 1.4(3) . ? C10 C11 1.4(3) . ? C12 C13 1.5(3) . ? C13 C18 1.4(3) . ? C13 C14 1.4(3) . ? C14 C15 1.4(2) . ? C15 C16 1.4(3) . ? C16 C17 1.4(3) . ? C17 C18 1.4(3) . ? C19 C20 1.5(3) . ? C20 C25 1.4(3) . ? C20 C21 1.4(3) . ? C21 C22 1.4(3) . ? C22 C23 1.4(3) . ? C23 C24 1.4(3) . ? C24 C25 1.4(3) . ? C26 C27 1.5(2) . ? C27 C28 1.4(3) . ? C27 C32 1.4(3) . ? C28 C29 1.4(2) . ? C29 C30 1.4(3) . ? C30 C31 1.4(3) . ? C31 C32 1.4(2) . ? C1S O1S 1.5(4) . ? C2S O2S 1.5(6) . ? N1 C33 1.3(3) . ? N1 C37 1.3(3) . ? C33 C34 1.4(3) . ? C34 C35 1.4(3) . ? C35 C36 1.4(3) . ? C35 C38 1.5(3) . ? C36 C37 1.4(3) . ? C38 C38 1.3(4) 3_976 ? N2 C39 1.3(5) . ? N2 C43 1.3(5) . ? C39 C40 1.4(4) . ? C40 C41 1.4(5) . ? C41 C42 1.4(5) . ? C41 C44 1.5(6) . ? C42 C43 1.4(4) . ? C44 C44 1.2(10) 3_567 ? N2X C43X 1.3(5) . ? N2X C39X 1.3(5) . ? C39X C40X 1.4(5) . ? C40X C41X 1.4(5) . ? C41X C42X 1.4(5) . ? C41X C44X 1.5(5) . ? C42X C43X 1.4(5) . ? C44X C44X 1.4(9) 3_567 ? 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 C9 C1 C4 120(10) . . ? C9 C1 C2 117(10) . . ? C4 C1 C2 90(10) . . ? C16 C2 C3 116(10) . . ? C16 C2 C1 118(10) . . ? C3 C2 C1 89(10) . . ? C30 C3 C2 118(10) . . ? C30 C3 C4 118(10) . . ? C2 C3 C4 90(10) . . ? C23 C4 C1 120(10) . . ? C23 C4 C3 119(10) . . ? C1 C4 C3 90(10) . . ? O2 C5 O1 123(10) . . ? O2 C5 C6 123(10) . . ? O1 C5 C6 114(10) . . ? C11 C6 C7 119(10) . . ? C11 C6 C5 120(10) . . ? C7 C6 C5 121(10) . . ? C6 C7 C8 120(10) . . ? C9 C8 C7 121(10) . . ? C8 C9 C10 118(10) . . ? C8 C9 C1 123(10) . . ? C10 C9 C1 119(10) . . ? C11 C10 C9 121(10) . . ? C10 C11 C6 121(10) . . ? O4 C12 O3 123(10) . . ? O4 C12 C13 121(10) . . ? O3 C12 C13 116(10) . . ? C18 C13 C14 119(10) . . ? C18 C13 C12 122(10) . . ? C14 C13 C12 119(10) . . ? C15 C14 C13 121(10) . . ? C14 C15 C16 121(10) . . ? C17 C16 C15 118(10) . . ? C17 C16 C2 121(10) . . ? C15 C16 C2 121(10) . . ? C18 C17 C16 121(10) . . ? C17 C18 C13 120(10) . . ? O5 C19 O6 120(10) . . ? O5 C19 C20 122(10) . . ? O6 C19 C20 118(10) . . ? C25 C20 C21 118(10) . . ? C25 C20 C19 122(10) . . ? C21 C20 C19 120(10) . . ? C20 C21 C22 121(10) . . ? C23 C22 C21 120(10) . . ? C22 C23 C24 117(10) . . ? C22 C23 C4 123(10) . . ? C24 C23 C4 120(10) . . ? C25 C24 C23 122(10) . . ? C24 C25 C20 120(10) . . ? O8 C26 O7 124(10) . . ? O8 C26 C27 123(10) . . ? O7 C26 C27 114(10) . . ? C28 C27 C32 119(10) . . ? C28 C27 C26 122(10) . . ? C32 C27 C26 119(10) . . ? C29 C28 C27 121(10) . . ? C28 C29 C30 121(10) . . ? C29 C30 C31 118(10) . . ? C29 C30 C3 122(10) . . ? C31 C30 C3 119(10) . . ? C32 C31 C30 121(10) . . ? C31 C32 C27 120(10) . . ? C33 N1 C37 117(10) . . ? N1 C33 C34 123(10) . . ? C33 C34 C35 120(10) . . ? C36 C35 C34 116(10) . . ? C36 C35 C38 123(10) . . ? C34 C35 C38 121(10) . . ? C37 C36 C35 120(10) . . ? N1 C37 C36 123(10) . . ? C38 C38 C35 127(10) 3_976 . ? C39 N2 C43 118(10) . . ? N2 C39 C40 122(10) . . ? C39 C40 C41 121(10) . . ? C42 C41 C40 118(10) . . ? C42 C41 C44 125(10) . . ? C40 C41 C44 117(10) . . ? C41 C42 C43 118(10) . . ? N2 C43 C42 123(10) . . ? C44 C44 C41 135(10) 3_567 . ? C43X N2X C39X 119(10) . . ? N2X C39X C40X 121(10) . . ? C41X C40X C39X 119(10) . . ? C40X C41X C42X 119(10) . . ? C40X C41X C44X 120(10) . . ? C42X C41X C44X 121(10) . . ? C43X C42X C41X 119(10) . . ? N2X C43X C42X 123(10) . . ? C44X C44X C41X 127(10) 3_567 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.83 1.82 2.6(2) 171.5 . O6 H6 O1S 0.83 1.83 2.6(4) 164.2 . O6 H6 O2S 0.83 2.01 2.8(16) 157.0 . O7 H7 N2X 0.83 1.82 2.6(4) 169.8 . O7 H7 N2 0.83 1.84 2.7(4) 171.3 . O1S H1S O5 0.83 2.03 2.7(5) 143.8 3_777 O2S H2S O5 0.83 1.96 2.6(14) 136.6 3_777 O2S H2S O2S 0.83 2.09 3(2) 122.1 3_777 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.516 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.053 data_9220n _database_code_depnum_ccdc_archive 'CCDC 873781' #TrackingRef 'GK8CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H54 N6 O10' _chemical_formula_weight 995.07 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 Pna2(1) 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 18.6545(8) _cell_length_b 12.6058(5) _cell_length_c 21.7602(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5117.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6082 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 26.61 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9500 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29348 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7250 _reflns_number_gt 6089 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 7250 _refine_ls_number_parameters 613 _refine_ls_number_restraints 307 _refine_ls_R_factor_all 0.1559 _refine_ls_R_factor_gt 0.1443 _refine_ls_wR_factor_ref 0.3719 _refine_ls_wR_factor_gt 0.3535 _refine_ls_goodness_of_fit_ref 1.632 _refine_ls_restrained_S_all 1.674 _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 C1S C 0.0678(5) 0.1231(7) 0.4891(5) 0.057(2) Uani 1 1 d . . . H1S H 0.0523 0.1054 0.5295 0.068 Uiso 1 1 calc R . . C2S C 0.0094(9) -0.0314(9) 0.4596(7) 0.108(5) Uani 1 1 d U . . H2S1 H -0.0069 -0.0294 0.5024 0.163 Uiso 1 1 calc R . . H2S2 H 0.0398 -0.0939 0.4533 0.163 Uiso 1 1 calc R . . H2S3 H -0.0322 -0.0353 0.4322 0.163 Uiso 1 1 calc R . . C3S C 0.0810(11) 0.0802(15) 0.3841(9) 0.160(8) Uani 1 1 d U . . H3S1 H 0.1193 0.1331 0.3876 0.240 Uiso 1 1 calc R . . H3S2 H 0.0439 0.1065 0.3561 0.240 Uiso 1 1 calc R . . H3S3 H 0.1009 0.0138 0.3680 0.240 Uiso 1 1 calc R . . N1S N 0.0487(5) 0.0605(6) 0.4466(5) 0.073(3) Uani 1 1 d U . . O1S O 0.1036(4) 0.2033(6) 0.4842(5) 0.086(3) Uani 1 1 d . . . C4S C 0.6847(5) 0.6051(8) 0.5071(6) 0.066(3) Uani 1 1 d . . . H4S H 0.6666 0.5759 0.5443 0.079 Uiso 1 1 calc R . . C5S C 0.7700(10) 0.5924(13) 0.4280(10) 0.166(8) Uani 1 1 d U . . H5S1 H 0.7360 0.6291 0.4011 0.248 Uiso 1 1 calc R . . H5S2 H 0.7933 0.5349 0.4051 0.248 Uiso 1 1 calc R . . H5S3 H 0.8064 0.6426 0.4423 0.248 Uiso 1 1 calc R . . C6S C 0.7596(7) 0.4452(8) 0.4920(9) 0.109(5) Uani 1 1 d U . . H6S1 H 0.8104 0.4488 0.5031 0.163 Uiso 1 1 calc R . . H6S2 H 0.7537 0.3998 0.4558 0.163 Uiso 1 1 calc R . . H6S3 H 0.7323 0.4156 0.5265 0.163 Uiso 1 1 calc R . . N2S N 0.7336(7) 0.5503(7) 0.4783(7) 0.109(4) Uani 1 1 d U . . O2S O 0.6599(6) 0.6902(6) 0.4909(6) 0.129(5) Uani 1 1 d . . . O1 O 0.4364(2) 0.7040(3) 0.3063(3) 0.0319(10) Uani 1 1 d U . . H1 H 0.4765 0.7140 0.2898 0.048 Uiso 1 1 calc R . . O2 O 0.4662(3) 0.5330(4) 0.2921(3) 0.0420(14) Uani 1 1 d U . . O3 O -0.1918(2) 0.2930(3) 0.3120(3) 0.0318(12) Uani 1 1 d . . . H3 H -0.2303 0.2812 0.2932 0.048 Uiso 1 1 calc R . . O4 O -0.2088(2) 0.4578(3) 0.2781(3) 0.0369(13) Uani 1 1 d . . . O5 O -0.1911(2) 0.7192(4) 0.6069(3) 0.0328(12) Uani 1 1 d U . . H5 H -0.2310 0.7264 0.6243 0.049 Uiso 1 1 calc R . . O6 O -0.2055(2) 0.5517(4) 0.6367(2) 0.0335(12) Uani 1 1 d . . . O7 O 0.4408(2) 0.2942(3) 0.6080(3) 0.0391(13) Uani 1 1 d . . . H7 H 0.4819 0.2876 0.6233 0.059 Uiso 1 1 calc R . . O8 O 0.4643(3) 0.4653(4) 0.6193(3) 0.0380(13) Uani 1 1 d . . . C1 C 0.1560(3) 0.4608(5) 0.4144(3) 0.0292(15) Uani 1 1 d U . . H1A H 0.1435 0.3927 0.3933 0.035 Uiso 1 1 calc R . . C2 C 0.0926(3) 0.5415(5) 0.4127(3) 0.0247(14) Uani 1 1 d U . . H2 H 0.1056 0.6077 0.3899 0.030 Uiso 1 1 calc R . . C3 C 0.1002(3) 0.5562(5) 0.4853(3) 0.0289(15) Uani 1 1 d . . . H3A H 0.1316 0.6189 0.4937 0.035 Uiso 1 1 calc R . . C4 C 0.1472(3) 0.4526(5) 0.4865(3) 0.0269(15) Uani 1 1 d . . . H4 H 0.1161 0.3904 0.4967 0.032 Uiso 1 1 calc R . . C5 C 0.2262(2) 0.5062(4) 0.3914(2) 0.0408(18) Uani 1 1 d GU . . C6 C 0.2410(2) 0.6137(4) 0.3852(2) 0.055(2) Uani 1 1 d GU . . H6 H 0.2072 0.6650 0.3987 0.065 Uiso 1 1 calc R . . C7 C 0.3054(2) 0.6463(3) 0.3591(3) 0.0393(19) Uani 1 1 d GU . . H7A H 0.3156 0.7197 0.3548 0.047 Uiso 1 1 calc R . . C8 C 0.3549(2) 0.5713(3) 0.3393(2) 0.0356(17) Uani 1 1 d GU . . C9 C 0.3400(2) 0.4638(3) 0.3455(3) 0.044(2) Uani 1 1 d GU . . H9 H 0.3739 0.4125 0.3320 0.053 Uiso 1 1 calc R . . C10 C 0.2756(3) 0.4312(3) 0.3716(2) 0.043(2) Uani 1 1 d GU . . H10 H 0.2655 0.3578 0.3759 0.051 Uiso 1 1 calc R . . C11 C 0.4236(3) 0.6000(5) 0.3103(4) 0.0319(10) Uani 1 1 d U . . C12 C 0.02076(19) 0.4953(4) 0.3905(2) 0.0371(17) Uani 1 1 d GU . . C13 C 0.0003(2) 0.3898(4) 0.3969(2) 0.053(2) Uani 1 1 d GU . . H13 H 0.0298 0.3419 0.4193 0.064 Uiso 1 1 calc R . . C14 C -0.0633(2) 0.3544(3) 0.3707(3) 0.0353(17) Uani 1 1 d GU . . H14 H -0.0773 0.2823 0.3751 0.042 Uiso 1 1 calc R . . C15 C -0.1064(2) 0.4245(3) 0.3381(2) 0.0294(15) Uani 1 1 d GU . . C16 C -0.0860(2) 0.5299(3) 0.3317(2) 0.0428(19) Uani 1 1 d GU . . H16 H -0.1155 0.5778 0.3094 0.051 Uiso 1 1 calc R . . C17 C -0.0224(2) 0.5653(3) 0.3579(2) 0.0407(18) Uani 1 1 d GU . . H17 H -0.0084 0.6374 0.3535 0.049 Uiso 1 1 calc R . . C18 C -0.1743(3) 0.3951(5) 0.3062(3) 0.0252(14) Uani 1 1 d . . . C19 C 0.03247(19) 0.5660(4) 0.5229(2) 0.0424(18) Uani 1 1 d GU . . C20 C -0.0042(2) 0.4816(3) 0.5494(2) 0.048(2) Uani 1 1 d GU . . H20 H 0.0154 0.4121 0.5477 0.058 Uiso 1 1 calc R . . C21 C -0.0697(2) 0.4988(3) 0.5782(2) 0.0386(18) Uani 1 1 d GU . . H21 H -0.0947 0.4411 0.5963 0.046 Uiso 1 1 calc R . . C22 C -0.09845(19) 0.6004(3) 0.5806(2) 0.0300(15) Uani 1 1 d GU . . C23 C -0.0618(2) 0.6848(3) 0.5542(2) 0.042(2) Uani 1 1 d GU . . H23 H -0.0814 0.7543 0.5558 0.051 Uiso 1 1 calc R . . C24 C 0.0037(2) 0.6676(4) 0.5253(2) 0.046(2) Uani 1 1 d GU . . H24 H 0.0288 0.7253 0.5073 0.055 Uiso 1 1 calc R . . C25 C -0.1704(3) 0.6200(5) 0.6111(3) 0.0236(13) Uani 1 1 d U . . C26 C 0.21622(19) 0.4475(4) 0.5251(2) 0.0392(18) Uani 1 1 d GU . . C27 C 0.2412(2) 0.3446(3) 0.5335(2) 0.047(2) Uani 1 1 d GU . . H27 H 0.2126 0.2860 0.5211 0.056 Uiso 1 1 calc R . . C28 C 0.3080(2) 0.3275(3) 0.5600(2) 0.0389(18) Uani 1 1 d GU . . H28 H 0.3251 0.2572 0.5657 0.047 Uiso 1 1 calc R . . C29 C 0.34979(18) 0.4132(3) 0.5781(2) 0.0270(15) Uani 1 1 d GU . . C30 C 0.3248(2) 0.5161(3) 0.5697(3) 0.0390(18) Uani 1 1 d GU . . H30 H 0.3534 0.5747 0.5821 0.047 Uiso 1 1 calc R . . C31 C 0.2580(2) 0.5332(3) 0.5432(2) 0.051(2) Uani 1 1 d GU . . H31 H 0.2409 0.6035 0.5375 0.061 Uiso 1 1 calc R . . C32 C 0.4241(4) 0.3943(5) 0.6050(3) 0.0296(15) Uani 1 1 d . . . N1 N 0.5693(3) 0.7370(4) 0.2632(3) 0.0275(13) Uani 1 1 d U . . N2 N 0.9258(3) 0.7681(4) 0.1504(3) 0.0326(15) Uani 1 1 d . . . N3 N -0.1790(3) 0.2504(4) 0.1554(3) 0.0242(13) Uani 1 1 d . . . N4 N 0.1790(3) 0.2432(4) 0.2618(3) 0.0244(12) Uani 1 1 d U . . C33 C 0.5962(3) 0.8281(5) 0.2429(4) 0.0351(18) Uani 1 1 d U . . H33 H 0.5665 0.8893 0.2438 0.042 Uiso 1 1 calc R . . C34 C 0.6658(3) 0.8387(5) 0.2203(4) 0.0301(17) Uani 1 1 d U . . H34 H 0.6823 0.9054 0.2057 0.036 Uiso 1 1 calc R . . C35 C 0.7107(3) 0.7511(4) 0.2192(3) 0.0164(13) Uani 1 1 d U . . C36 C 0.6827(3) 0.6559(5) 0.2429(4) 0.0338(18) Uani 1 1 d U . . H36 H 0.7120 0.5945 0.2464 0.041 Uiso 1 1 calc R . . C37 C 0.6117(4) 0.6536(5) 0.2611(4) 0.0365(18) Uani 1 1 d U . . H37 H 0.5922 0.5870 0.2729 0.044 Uiso 1 1 calc R . . C38 C 0.8958(4) 0.6767(5) 0.1673(4) 0.0369(19) Uani 1 1 d . . . H38 H 0.9237 0.6139 0.1637 0.044 Uiso 1 1 calc R . . C39 C 0.8276(4) 0.6674(5) 0.1893(4) 0.0319(17) Uani 1 1 d . . . H39 H 0.8093 0.5997 0.2003 0.038 Uiso 1 1 calc R . . C40 C 0.7855(3) 0.7564(5) 0.1954(3) 0.0219(14) Uani 1 1 d . . . C41 C 0.8156(4) 0.8518(5) 0.1786(4) 0.0367(19) Uani 1 1 d . . . H41 H 0.7890 0.9156 0.1827 0.044 Uiso 1 1 calc R . . C42 C 0.8851(3) 0.8541(5) 0.1559(4) 0.0352(18) Uani 1 1 d . . . H42 H 0.9045 0.9205 0.1435 0.042 Uiso 1 1 calc R . . C43 C -0.1393(3) 0.3378(4) 0.1535(3) 0.0224(14) Uani 1 1 d . . . H43 H -0.1599 0.4003 0.1365 0.027 Uiso 1 1 calc R . . C44 C -0.0695(3) 0.3427(4) 0.1749(3) 0.0205(14) Uani 1 1 d . . . H44 H -0.0434 0.4073 0.1731 0.025 Uiso 1 1 calc R . . C45 C -0.0385(3) 0.2530(5) 0.1985(3) 0.0211(14) Uani 1 1 d U . . C46 C -0.0804(3) 0.1612(5) 0.2009(4) 0.0289(17) Uani 1 1 d . . . H46 H -0.0613 0.0975 0.2175 0.035 Uiso 1 1 calc R . . C47 C -0.1480(4) 0.1639(5) 0.1794(4) 0.0310(16) Uani 1 1 d . . . H47 H -0.1755 0.1005 0.1814 0.037 Uiso 1 1 calc R . . C48 C 0.1487(3) 0.1583(5) 0.2359(4) 0.0288(16) Uani 1 1 d U . . H48 H 0.1766 0.0957 0.2313 0.035 Uiso 1 1 calc R . . C49 C 0.0778(3) 0.1574(5) 0.2153(3) 0.0248(15) Uani 1 1 d U . . H49 H 0.0576 0.0947 0.1984 0.030 Uiso 1 1 calc R . . C50 C 0.0367(3) 0.2505(4) 0.2200(3) 0.0121(12) Uani 1 1 d U . . C51 C 0.0701(3) 0.3384(5) 0.2462(3) 0.0221(14) Uani 1 1 d U . . H51 H 0.0443 0.4029 0.2509 0.027 Uiso 1 1 calc R . . C52 C 0.1409(3) 0.3323(5) 0.2655(3) 0.0250(14) Uani 1 1 d U . . H52 H 0.1630 0.3940 0.2819 0.030 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 C1S 0.045(5) 0.051(5) 0.075(7) 0.004(5) -0.011(5) 0.003(4) C2S 0.137(11) 0.078(7) 0.111(11) -0.011(7) 0.042(9) -0.042(7) C3S 0.192(16) 0.164(13) 0.124(13) -0.045(11) 0.036(13) -0.057(12) N1S 0.105(7) 0.048(4) 0.065(6) -0.015(4) 0.007(5) -0.027(4) O1S 0.072(5) 0.071(5) 0.116(7) 0.019(4) -0.008(5) -0.037(4) C4S 0.051(5) 0.060(6) 0.087(8) -0.003(5) 0.026(5) -0.003(5) C5S 0.188(14) 0.148(12) 0.161(14) 0.063(11) 0.110(12) 0.088(11) C6S 0.093(8) 0.060(6) 0.173(14) -0.038(7) 0.014(9) -0.025(6) N2S 0.130(9) 0.057(5) 0.139(9) 0.001(6) 0.084(8) 0.007(5) O2S 0.134(9) 0.079(6) 0.175(12) 0.000(6) 0.085(8) 0.037(6) O1 0.0144(17) 0.0237(18) 0.057(3) -0.0010(17) 0.0216(19) -0.0051(13) O2 0.037(3) 0.030(2) 0.059(4) -0.006(2) 0.024(3) -0.006(2) O3 0.016(2) 0.020(2) 0.059(3) 0.000(2) -0.014(2) -0.0025(17) O4 0.027(3) 0.028(2) 0.056(4) 0.005(2) -0.014(3) -0.0003(19) O5 0.013(2) 0.037(2) 0.048(3) 0.004(2) 0.018(2) 0.0070(18) O6 0.026(2) 0.040(3) 0.035(3) 0.002(2) 0.015(2) 0.006(2) O7 0.022(2) 0.027(2) 0.068(4) 0.002(2) -0.020(3) 0.0005(18) O8 0.031(3) 0.033(2) 0.050(4) -0.014(2) -0.016(3) 0.005(2) C1 0.021(3) 0.040(3) 0.026(3) -0.008(3) 0.000(3) -0.007(3) C2 0.014(3) 0.031(3) 0.029(3) 0.005(3) -0.001(3) -0.006(2) C3 0.013(3) 0.039(4) 0.035(4) -0.002(3) -0.005(3) -0.003(3) C4 0.009(3) 0.039(4) 0.033(4) -0.005(3) 0.006(3) -0.005(3) C5 0.035(3) 0.065(4) 0.023(3) 0.010(3) -0.014(3) -0.036(3) C6 0.031(4) 0.102(6) 0.031(4) -0.022(4) 0.001(4) 0.006(4) C7 0.014(3) 0.065(4) 0.039(4) -0.023(3) 0.008(3) -0.015(3) C8 0.032(4) 0.050(4) 0.025(4) -0.011(3) 0.014(3) -0.017(3) C9 0.048(4) 0.049(4) 0.034(4) -0.004(3) -0.001(4) -0.029(3) C10 0.032(4) 0.057(4) 0.038(4) 0.009(3) 0.003(3) -0.026(3) C11 0.0144(17) 0.0237(18) 0.057(3) -0.0010(17) 0.0216(19) -0.0051(13) C12 0.022(3) 0.048(4) 0.042(4) -0.019(3) 0.021(3) -0.020(3) C13 0.031(4) 0.088(6) 0.039(4) 0.000(4) -0.007(4) 0.023(4) C14 0.016(3) 0.057(4) 0.032(4) 0.013(3) -0.005(3) -0.001(3) C15 0.019(3) 0.049(4) 0.020(3) 0.006(3) -0.006(3) -0.016(3) C16 0.051(4) 0.044(4) 0.033(4) -0.002(3) -0.001(4) -0.025(3) C17 0.033(4) 0.050(4) 0.040(4) -0.006(3) 0.003(3) -0.014(3) C18 0.018(3) 0.030(3) 0.028(3) 0.004(3) -0.011(3) -0.009(3) C19 0.032(4) 0.069(4) 0.026(4) -0.014(3) -0.001(3) -0.008(3) C20 0.047(4) 0.055(4) 0.043(4) -0.034(3) -0.029(3) 0.038(3) C21 0.029(4) 0.048(4) 0.040(4) -0.010(3) -0.009(3) 0.020(3) C22 0.016(3) 0.052(4) 0.022(3) -0.004(3) -0.001(3) 0.012(3) C23 0.021(3) 0.070(5) 0.036(4) 0.018(4) 0.014(3) 0.018(3) C24 0.020(3) 0.086(5) 0.032(4) 0.008(4) 0.008(3) 0.008(3) C25 0.010(3) 0.027(3) 0.034(3) -0.002(3) 0.008(3) 0.000(2) C26 0.022(3) 0.076(5) 0.019(4) -0.001(3) -0.002(3) 0.002(3) C27 0.017(3) 0.083(5) 0.040(4) -0.004(4) -0.013(3) 0.017(3) C28 0.017(3) 0.063(4) 0.036(4) -0.009(3) -0.009(3) 0.008(3) C29 0.017(3) 0.037(3) 0.027(3) -0.011(3) -0.007(3) 0.020(3) C30 0.046(4) 0.044(4) 0.028(4) -0.001(3) -0.012(3) 0.018(3) C31 0.056(5) 0.062(5) 0.035(4) 0.011(3) 0.015(4) 0.049(4) C32 0.028(3) 0.037(4) 0.024(3) -0.008(3) -0.014(3) 0.005(3) N1 0.014(3) 0.030(3) 0.038(3) -0.001(2) 0.009(3) -0.004(2) N2 0.020(3) 0.031(3) 0.046(4) 0.009(3) 0.015(3) 0.002(2) N3 0.014(2) 0.019(2) 0.039(4) 0.002(2) -0.007(3) 0.0022(19) N4 0.011(2) 0.039(3) 0.024(3) 0.004(2) -0.009(2) 0.003(2) C33 0.019(3) 0.026(3) 0.060(5) -0.001(3) 0.015(3) 0.005(3) C34 0.023(3) 0.017(3) 0.051(4) 0.000(3) 0.020(3) -0.009(2) C35 0.013(3) 0.017(3) 0.019(3) -0.003(2) 0.005(2) -0.003(2) C36 0.011(3) 0.027(3) 0.064(5) 0.009(3) 0.012(3) 0.001(2) C37 0.022(3) 0.028(3) 0.059(5) 0.015(3) 0.016(3) -0.004(3) C38 0.020(3) 0.033(3) 0.058(5) 0.008(3) 0.021(4) 0.003(3) C39 0.024(3) 0.022(3) 0.049(5) 0.000(3) 0.015(3) 0.000(3) C40 0.012(3) 0.030(3) 0.024(4) 0.007(3) 0.002(3) -0.008(2) C41 0.030(4) 0.025(3) 0.055(5) 0.006(3) 0.017(4) -0.006(3) C42 0.013(3) 0.031(3) 0.061(5) 0.014(3) 0.016(3) 0.001(2) C43 0.016(3) 0.020(3) 0.031(4) 0.004(3) -0.010(3) 0.000(2) C44 0.021(3) 0.017(3) 0.024(3) 0.004(2) 0.000(3) 0.005(2) C45 0.010(3) 0.034(3) 0.019(3) -0.006(3) 0.002(2) 0.007(2) C46 0.018(3) 0.024(3) 0.045(5) 0.000(3) -0.004(3) -0.009(2) C47 0.020(3) 0.031(3) 0.043(5) 0.000(3) -0.009(3) -0.009(3) C48 0.016(3) 0.025(3) 0.045(4) -0.005(3) -0.007(3) 0.002(2) C49 0.019(3) 0.022(3) 0.033(4) -0.004(3) -0.011(3) 0.001(2) C50 0.009(3) 0.016(2) 0.012(3) -0.003(2) -0.006(2) 0.007(2) C51 0.013(3) 0.026(3) 0.027(4) 0.002(3) -0.003(3) 0.009(2) C52 0.017(3) 0.029(3) 0.029(4) 0.000(3) -0.002(3) -0.004(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 C1S O1S 1.216(11) . ? C1S N1S 1.268(13) . ? C2S N1S 1.401(13) . ? C3S N1S 1.51(2) . ? C4S O2S 1.220(13) . ? C4S N2S 1.305(13) . ? C5S N2S 1.394(18) . ? C6S N2S 1.442(15) . ? O1 C11 1.336(7) . ? O2 C11 1.224(8) . ? O3 C18 1.334(7) . ? O4 C18 1.190(8) . ? O5 C25 1.312(7) . ? O6 C25 1.218(8) . ? O7 C32 1.302(8) . ? O8 C32 1.208(8) . ? C1 C5 1.514(7) . ? C1 C2 1.560(10) . ? C1 C4 1.582(10) . ? C2 C12 1.539(7) . ? C2 C3 1.596(10) . ? C3 C19 1.511(7) . ? C3 C4 1.574(10) . ? C4 C26 1.538(7) . ? C5 C6 1.3900 . ? C5 C10 1.3900 . ? C6 C7 1.3900 . ? C7 C8 1.3900 . ? C8 C9 1.3900 . ? C8 C11 1.474(6) . ? C9 C10 1.3900 . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C15 C18 1.489(6) . ? C16 C17 1.3900 . ? C19 C20 1.3900 . ? C19 C24 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C22 C23 1.3900 . ? C22 C25 1.517(6) . ? C23 C24 1.3900 . ? C26 C27 1.3900 . ? C26 C31 1.3900 . ? C27 C28 1.3900 . ? C28 C29 1.3900 . ? C29 C30 1.3900 . ? C29 C32 1.524(7) . ? C30 C31 1.3900 . ? N1 C37 1.318(8) . ? N1 C33 1.330(8) . ? N2 C42 1.329(8) . ? N2 C38 1.333(8) . ? N3 C43 1.328(7) . ? N3 C47 1.341(8) . ? N4 C52 1.332(8) . ? N4 C48 1.335(8) . ? C33 C34 1.394(9) . ? C34 C35 1.385(8) . ? C35 C36 1.407(8) . ? C35 C40 1.490(7) . ? C36 C37 1.382(9) . ? C38 C39 1.364(9) . ? C39 C40 1.376(9) . ? C40 C41 1.376(8) . ? C41 C42 1.388(9) . ? C43 C44 1.385(9) . ? C44 C45 1.370(8) . ? C45 C46 1.397(8) . ? C45 C50 1.479(7) . ? C46 C47 1.345(9) . ? C48 C49 1.397(9) . ? C49 C50 1.405(8) . ? C50 C51 1.394(8) . ? C51 C52 1.387(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1S C1S N1S 127.4(12) . . ? C1S N1S C2S 121.0(11) . . ? C1S N1S C3S 116.4(10) . . ? C2S N1S C3S 121.9(10) . . ? O2S C4S N2S 126.3(12) . . ? C4S N2S C5S 121.1(10) . . ? C4S N2S C6S 128.5(12) . . ? C5S N2S C6S 110.4(11) . . ? C5 C1 C2 113.7(5) . . ? C5 C1 C4 116.2(5) . . ? C2 C1 C4 89.3(5) . . ? C12 C2 C1 114.8(5) . . ? C12 C2 C3 115.6(5) . . ? C1 C2 C3 89.2(5) . . ? C19 C3 C4 121.6(5) . . ? C19 C3 C2 118.1(5) . . ? C4 C3 C2 88.3(5) . . ? C26 C4 C3 120.7(5) . . ? C26 C4 C1 117.2(5) . . ? C3 C4 C1 89.2(5) . . ? C6 C5 C10 120.0 . . ? C6 C5 C1 125.0(4) . . ? C10 C5 C1 114.8(4) . . ? C7 C6 C5 120.0 . . ? C6 C7 C8 120.0 . . ? C7 C8 C9 120.0 . . ? C7 C8 C11 122.9(4) . . ? C9 C8 C11 117.1(4) . . ? C10 C9 C8 120.0 . . ? C9 C10 C5 120.0 . . ? O2 C11 O1 122.8(5) . . ? O2 C11 C8 122.2(5) . . ? O1 C11 C8 115.1(5) . . ? C13 C12 C17 120.0 . . ? C13 C12 C2 124.8(4) . . ? C17 C12 C2 115.1(4) . . ? C12 C13 C14 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 C18 115.1(3) . . ? C14 C15 C18 124.8(3) . . ? C15 C16 C17 120.0 . . ? C16 C17 C12 120.0 . . ? O4 C18 O3 123.9(6) . . ? O4 C18 C15 122.3(5) . . ? O3 C18 C15 113.8(5) . . ? C20 C19 C24 120.0 . . ? C20 C19 C3 125.0(4) . . ? C24 C19 C3 114.7(4) . . ? C19 C20 C21 120.0 . . ? C22 C21 C20 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 C25 119.4(3) . . ? C21 C22 C25 120.6(3) . . ? C22 C23 C24 120.0 . . ? C23 C24 C19 120.0 . . ? O6 C25 O5 123.2(5) . . ? O6 C25 C22 124.1(5) . . ? O5 C25 C22 112.7(5) . . ? C27 C26 C31 120.0 . . ? C27 C26 C4 113.1(4) . . ? C31 C26 C4 126.3(4) . . ? C28 C27 C26 120.0 . . ? C27 C28 C29 120.0 . . ? C30 C29 C28 120.0 . . ? C30 C29 C32 120.1(3) . . ? C28 C29 C32 119.8(3) . . ? C29 C30 C31 120.0 . . ? C30 C31 C26 120.0 . . ? O8 C32 O7 123.9(6) . . ? O8 C32 C29 123.2(5) . . ? O7 C32 C29 112.8(5) . . ? C37 N1 C33 116.8(5) . . ? C42 N2 C38 116.2(6) . . ? C43 N3 C47 116.5(5) . . ? C52 N4 C48 118.4(5) . . ? N1 C33 C34 123.5(6) . . ? C35 C34 C33 119.5(5) . . ? C34 C35 C36 116.7(5) . . ? C34 C35 C40 122.4(5) . . ? C36 C35 C40 120.9(5) . . ? C37 C36 C35 118.6(6) . . ? N1 C37 C36 124.7(6) . . ? N2 C38 C39 124.2(6) . . ? C38 C39 C40 119.8(6) . . ? C41 C40 C39 117.0(6) . . ? C41 C40 C35 120.9(5) . . ? C39 C40 C35 122.1(5) . . ? C40 C41 C42 119.6(6) . . ? N2 C42 C41 123.2(6) . . ? N3 C43 C44 123.4(5) . . ? C45 C44 C43 119.1(6) . . ? C44 C45 C46 117.5(6) . . ? C44 C45 C50 122.4(6) . . ? C46 C45 C50 120.1(5) . . ? C47 C46 C45 119.4(6) . . ? N3 C47 C46 124.1(6) . . ? N4 C48 C49 122.8(6) . . ? C48 C49 C50 119.2(5) . . ? C51 C50 C49 116.6(5) . . ? C51 C50 C45 122.5(5) . . ? C49 C50 C45 120.9(5) . . ? C52 C51 C50 120.4(5) . . ? N4 C52 C51 122.4(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.84 1.85 2.683(7) 172.9 . O3 H3 N4 0.84 1.85 2.686(7) 172.4 3_455 O5 H5 N3 0.84 1.83 2.671(7) 174.0 4_455 O7 H7 N2 0.84 1.84 2.675(7) 174.9 4_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.454 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.200 data_9220pnna _database_code_depnum_ccdc_archive 'CCDC 873782' #TrackingRef '- GK8CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H54 N6 O10' _chemical_formula_weight 995.07 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 Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 18.6545(8) _cell_length_b 21.7602(9) _cell_length_c 12.6058(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5117.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6082 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 26.61 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9500 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28829 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4510 _reflns_number_gt 3924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+15.2294P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4510 _refine_ls_number_parameters 445 _refine_ls_number_restraints 52 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.2127 _refine_ls_wR_factor_gt 0.2089 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.209 _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 N1 N 0.07074(16) 0.55311(15) 0.4975(3) 0.0344(8) Uani 1 1 d . . . N2 N 0.17844(17) 0.55619(17) 0.0157(3) 0.0402(9) Uani 1 1 d . . . O1 O 0.05895(14) 0.39753(15) 0.5370(2) 0.0429(8) Uani 1 1 d . . . H1 H 0.0173 0.4114 0.5294 0.064 Uiso 1 1 calc R . . O2 O 0.04278(15) 0.42901(14) 0.7035(2) 0.0450(8) Uani 1 1 d . . . O3 O 0.68877(15) 0.40086(16) 0.9550(2) 0.0480(8) Uani 1 1 d . . . H3 H 0.7314 0.4124 0.9625 0.072 Uiso 1 1 calc R . . O4 O 0.71508(16) 0.41354(15) 0.7847(2) 0.0487(8) Uani 1 1 d . . . C1 C 0.0781(2) 0.40217(19) 0.6372(3) 0.0356(9) Uani 1 1 d . . . C9 C 0.6735(2) 0.3972(2) 0.8531(3) 0.0375(10) Uani 1 1 d . . . C2 C 0.15331(9) 0.37318(11) 0.6480(3) 0.028(2) Uani 0.50 1 d PG . 1 C3 C 0.18196(8) 0.37061(11) 0.7497(3) 0.029(2) Uani 0.50 1 d PG . 1 H3A H 0.1573 0.3894 0.8072 0.035 Uiso 0.50 1 calc PR . 1 C4 C 0.24662(8) 0.34056(9) 0.7673(2) 0.026(2) Uani 0.50 1 d PG . 1 H4 H 0.2662 0.3388 0.8368 0.031 Uiso 0.50 1 calc PR . 1 C5 C 0.28264(9) 0.31308(8) 0.68325(19) 0.0213(16) Uani 0.50 1 d PG . 1 C6 C 0.25399(11) 0.31565(12) 0.5816(2) 0.0314(19) Uani 0.50 1 d PG . 1 H6 H 0.2786 0.2969 0.5241 0.038 Uiso 0.50 1 calc PR . 1 C7 C 0.18932(11) 0.34570(13) 0.5639(2) 0.036(3) Uani 0.50 1 d PG . 1 H7 H 0.1697 0.3475 0.4944 0.043 Uiso 0.50 1 calc PR . 1 C10 C 0.59606(9) 0.37272(10) 0.8420(3) 0.024(2) Uani 0.50 1 d PG . 1 C11 C 0.57179(8) 0.36232(11) 0.7393(3) 0.029(2) Uani 0.50 1 d PG . 1 H11 H 0.6000 0.3749 0.6804 0.035 Uiso 0.50 1 calc PR . 1 C12 C 0.50622(8) 0.33356(9) 0.7227(2) 0.023(2) Uani 0.50 1 d PG . 1 H12 H 0.4896 0.3265 0.6525 0.028 Uiso 0.50 1 calc PR . 1 C13 C 0.46491(9) 0.31517(7) 0.80881(19) 0.0176(16) Uani 0.50 1 d PG . 1 C14 C 0.48918(11) 0.32557(12) 0.9115(2) 0.032(2) Uani 0.50 1 d PG . 1 H14 H 0.4609 0.3130 0.9704 0.038 Uiso 0.50 1 calc PR . 1 C15 C 0.55475(11) 0.35434(13) 0.9281(2) 0.035(2) Uani 0.50 1 d PG . 1 H15 H 0.5713 0.3614 0.9983 0.042 Uiso 0.50 1 calc PR . 1 C22 C 0.14253(9) 0.37068(11) 0.6769(3) 0.026(2) Uani 0.50 1 d PG . 2 C23 C 0.16270(9) 0.37654(13) 0.7826(3) 0.033(2) Uani 0.50 1 d PG . 2 H23 H 0.1328 0.3983 0.8308 0.039 Uiso 0.50 1 calc PR . 2 C24 C 0.22654(9) 0.35064(12) 0.8177(2) 0.0277(18) Uani 0.50 1 d PG . 2 H24 H 0.2403 0.3546 0.8900 0.033 Uiso 0.50 1 calc PR . 2 C25 C 0.27021(8) 0.31888(8) 0.74719(19) 0.0215(19) Uani 0.50 1 d PG . 2 C26 C 0.25005(9) 0.31302(9) 0.6415(2) 0.029(2) Uani 0.50 1 d PG . 2 H26 H 0.2799 0.2913 0.5933 0.035 Uiso 0.50 1 calc PR . 2 C27 C 0.18621(10) 0.33892(11) 0.6064(2) 0.034(2) Uani 0.50 1 d PG . 2 H27 H 0.1724 0.3349 0.5342 0.041 Uiso 0.50 1 calc PR . 2 C30 C 0.60799(9) 0.36694(11) 0.8176(3) 0.026(2) Uani 0.50 1 d PG . 2 C31 C 0.59243(8) 0.36178(13) 0.7101(3) 0.033(2) Uani 0.50 1 d PG . 2 H31 H 0.6264 0.3750 0.6588 0.039 Uiso 0.50 1 calc PR . 2 C32 C 0.52715(9) 0.33734(12) 0.6778(2) 0.025(2) Uani 0.50 1 d PG . 2 H32 H 0.5165 0.3338 0.6043 0.030 Uiso 0.50 1 calc PR . 2 C33 C 0.47744(8) 0.31807(7) 0.75286(19) 0.0177(18) Uani 0.50 1 d PG . 2 C34 C 0.49301(10) 0.32323(9) 0.8603(2) 0.026(2) Uani 0.50 1 d PG . 2 H34 H 0.4590 0.3101 0.9116 0.031 Uiso 0.50 1 calc PR . 2 C35 C 0.55828(10) 0.34767(11) 0.8927(2) 0.032(2) Uani 0.50 1 d PG . 2 H35 H 0.5689 0.3512 0.9661 0.038 Uiso 0.50 1 calc PR . 2 C8 C 0.35055(9) 0.27597(7) 0.6950(2) 0.0219(15) Uani 0.50 1 d PGD . . C16 C 0.39666(9) 0.27758(7) 0.7982(2) 0.0217(15) Uani 0.50 1 d PGD . . C28 C 0.34257(9) 0.29644(7) 0.79108(19) 0.0208(14) Uani 0.50 1 d PGD . . C36 C 0.40564(9) 0.29480(7) 0.70986(19) 0.0206(14) Uani 0.50 1 d PGD . . H82 H 0.369(4) 0.290(5) 0.858(5) 0.050 Uiso 0.50 1 d PD . . H81 H 0.385(4) 0.277(4) 0.638(5) 0.050 Uiso 0.50 1 d PD . . H83 H 0.351(5) 0.312(4) 0.861(3) 0.050 Uiso 0.50 1 d PD . . H84 H 0.398(5) 0.308(4) 0.638(3) 0.050 Uiso 0.50 1 d PD . . C1X C 0.8170(4) 0.2180(5) 0.6260(6) 0.057(3) Uani 0.50 1 d PD A -1 H1X H 0.7987 0.1782 0.6418 0.068 Uiso 0.50 1 calc PR A -1 C2X C 0.8274(11) 0.3245(6) 0.6708(15) 0.156(8) Uani 0.50 1 d PDU A -1 H2X1 H 0.8515 0.3248 0.6017 0.234 Uiso 0.50 1 calc PR A -1 H2X2 H 0.8617 0.3359 0.7263 0.234 Uiso 0.50 1 calc PR A -1 H2X3 H 0.7877 0.3539 0.6701 0.234 Uiso 0.50 1 calc PR A -1 C3X C 0.7559(7) 0.2539(7) 0.7851(7) 0.076(4) Uani 0.50 1 d PDU A -1 H3X1 H 0.7155 0.2270 0.7669 0.114 Uiso 0.50 1 calc PR A -1 H3X2 H 0.7376 0.2934 0.8107 0.114 Uiso 0.50 1 calc PR A -1 H3X3 H 0.7847 0.2345 0.8409 0.114 Uiso 0.50 1 calc PR A -1 N1X N 0.8000(5) 0.2637(4) 0.6918(7) 0.071(3) Uani 0.50 1 d PDU A -1 O1X O 0.8547(4) 0.2236(5) 0.5461(5) 0.084(3) Uani 0.50 1 d PD A -1 C4X C 0.9346(5) 0.2987(5) 0.6488(7) 0.061(3) Uani 0.50 1 d PD B -2 H4X H 0.9135 0.3333 0.6825 0.074 Uiso 0.50 1 calc PR B -2 C5X C 0.9963(11) 0.2961(9) 0.8058(11) 0.129(8) Uani 0.50 1 d PDU B -2 H5X1 H 1.0316 0.3294 0.8010 0.193 Uiso 0.50 1 calc PR B -2 H5X2 H 1.0140 0.2644 0.8543 0.193 Uiso 0.50 1 calc PR B -2 H5X3 H 0.9508 0.3125 0.8324 0.193 Uiso 0.50 1 calc PR B -2 C6X C 1.0281(10) 0.2213(8) 0.6623(15) 0.123(8) Uani 0.50 1 d PDU B -2 H6X1 H 0.9972 0.1869 0.6416 0.185 Uiso 0.50 1 calc PR B -2 H6X2 H 1.0617 0.2077 0.7173 0.185 Uiso 0.50 1 calc PR B -2 H6X3 H 1.0550 0.2357 0.6003 0.185 Uiso 0.50 1 calc PR B -2 N2X N 0.9854(5) 0.2698(5) 0.7021(7) 0.088(3) Uani 0.50 1 d PDU B -2 O2X O 0.9117(5) 0.2856(4) 0.5599(6) 0.091(3) Uani 0.50 1 d PD B -2 C1S C 0.1017(2) 0.5287(2) 0.4113(3) 0.0391(10) Uani 1 1 d . . . H1S H 0.0742 0.5261 0.3480 0.047 Uiso 1 1 calc R . . C2S C 0.1711(2) 0.50727(19) 0.4093(3) 0.0347(9) Uani 1 1 d . . . H2S H 0.1907 0.4905 0.3461 0.042 Uiso 1 1 calc R . . C3S C 0.21210(18) 0.51062(16) 0.5016(3) 0.0259(8) Uani 1 1 d . . . C4S C 0.17984(19) 0.53564(17) 0.5916(3) 0.0299(8) Uani 1 1 d . . . H4S H 0.2057 0.5388 0.6563 0.036 Uiso 1 1 calc R . . C5S C 0.1098(2) 0.55577(18) 0.5853(3) 0.0331(9) Uani 1 1 d . . . H5S H 0.0884 0.5724 0.6474 0.040 Uiso 1 1 calc R . . C6S C 0.1498(2) 0.5386(2) -0.0746(3) 0.0499(12) Uani 1 1 d . . . H6S H 0.1785 0.5416 -0.1366 0.060 Uiso 1 1 calc R . . C7S C 0.0811(2) 0.5160(2) -0.0857(3) 0.0447(11) Uani 1 1 d . . . H7S H 0.0639 0.5034 -0.1532 0.054 Uiso 1 1 calc R . . C8S C 0.03744(19) 0.51192(16) 0.0034(3) 0.0278(8) Uani 1 1 d . . . C9S C 0.0668(2) 0.5317(2) 0.0977(3) 0.0429(11) Uani 1 1 d . . . H9S H 0.0391 0.5306 0.1609 0.051 Uiso 1 1 calc R . . C10S C 0.1364(2) 0.5530(2) 0.1003(3) 0.0461(12) Uani 1 1 d . . . H10S H 0.1553 0.5661 0.1665 0.055 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 N1 0.0216(16) 0.0400(18) 0.0415(19) 0.0033(16) 0.0000(14) 0.0084(14) N2 0.0258(17) 0.053(2) 0.041(2) -0.0044(17) -0.0044(15) -0.0140(16) O1 0.0213(14) 0.063(2) 0.0450(17) -0.0036(15) -0.0042(12) 0.0196(14) O2 0.0364(16) 0.0576(19) 0.0409(17) -0.0041(15) -0.0042(14) 0.0137(15) O3 0.0263(15) 0.080(2) 0.0378(17) -0.0028(16) -0.0024(13) -0.0254(15) O4 0.0422(17) 0.065(2) 0.0392(17) 0.0102(15) -0.0030(14) -0.0217(15) C1 0.025(2) 0.036(2) 0.045(2) -0.0021(19) -0.0058(18) 0.0035(17) C9 0.032(2) 0.044(2) 0.037(2) 0.0011(19) -0.0065(19) -0.0119(18) C2 0.014(4) 0.033(6) 0.036(5) 0.009(4) -0.001(4) 0.003(4) C3 0.020(4) 0.033(4) 0.034(5) -0.003(4) 0.002(4) 0.005(3) C4 0.027(5) 0.027(5) 0.024(5) -0.006(4) -0.004(4) 0.004(4) C5 0.011(4) 0.022(4) 0.031(5) -0.004(4) 0.003(3) 0.000(3) C6 0.028(4) 0.041(5) 0.026(4) -0.011(4) -0.007(4) 0.010(3) C7 0.024(5) 0.044(5) 0.040(6) -0.010(4) -0.012(4) 0.013(4) C10 0.018(4) 0.025(5) 0.030(4) 0.002(4) -0.006(4) -0.002(4) C11 0.022(4) 0.035(5) 0.030(5) 0.013(4) 0.002(4) 0.001(3) C12 0.023(5) 0.034(5) 0.011(5) 0.010(4) 0.000(4) -0.005(4) C13 0.007(4) 0.021(4) 0.024(5) 0.000(4) 0.003(3) 0.002(3) C14 0.029(4) 0.042(5) 0.025(6) 0.001(4) -0.002(4) -0.005(4) C15 0.025(5) 0.052(6) 0.028(5) -0.001(4) -0.004(3) -0.009(4) C22 0.018(4) 0.032(5) 0.029(4) 0.000(3) 0.004(4) -0.008(4) C23 0.018(4) 0.040(5) 0.040(5) -0.003(4) 0.000(4) 0.011(4) C24 0.024(4) 0.036(4) 0.023(5) -0.010(4) -0.003(3) 0.004(3) C25 0.020(4) 0.020(4) 0.024(4) -0.005(4) 0.004(4) -0.001(3) C26 0.024(4) 0.039(5) 0.024(5) -0.014(4) 0.004(4) 0.004(4) C27 0.025(5) 0.040(5) 0.037(6) -0.003(4) 0.004(4) 0.004(4) C30 0.020(4) 0.032(5) 0.027(4) -0.002(4) 0.008(4) 0.002(4) C31 0.025(4) 0.042(5) 0.032(5) -0.005(4) 0.000(4) -0.011(4) C32 0.021(4) 0.036(4) 0.019(5) 0.007(4) -0.002(3) -0.005(3) C33 0.017(4) 0.021(4) 0.015(4) 0.001(4) 0.009(4) -0.001(3) C34 0.015(4) 0.039(5) 0.024(6) 0.006(4) 0.002(4) -0.009(3) C35 0.028(5) 0.042(6) 0.026(5) 0.004(4) -0.007(4) -0.004(4) C8 0.017(3) 0.027(4) 0.022(4) 0.001(3) -0.003(3) -0.002(3) C16 0.015(3) 0.028(4) 0.022(4) -0.006(3) -0.002(3) -0.001(3) C28 0.015(3) 0.027(4) 0.021(4) -0.004(3) 0.002(3) -0.001(3) C36 0.017(3) 0.025(3) 0.020(4) 0.000(3) -0.002(3) 0.002(3) C1X 0.046(6) 0.075(7) 0.049(6) 0.006(5) -0.004(5) 0.005(5) C2X 0.215(16) 0.109(11) 0.143(13) -0.024(11) 0.065(13) -0.055(12) C3X 0.085(8) 0.088(8) 0.055(8) -0.002(8) 0.022(6) 0.005(8) N1X 0.087(6) 0.071(6) 0.054(5) -0.001(5) 0.020(5) -0.014(5) O1X 0.082(6) 0.122(7) 0.048(4) 0.003(5) 0.036(4) 0.000(5) C4X 0.044(6) 0.082(8) 0.058(7) 0.013(6) 0.009(5) 0.017(5) C5X 0.130(14) 0.173(16) 0.083(11) 0.047(11) -0.029(10) -0.068(13) C6X 0.117(14) 0.123(13) 0.131(14) -0.022(12) -0.052(11) 0.041(11) N2X 0.102(7) 0.104(7) 0.059(5) -0.008(5) -0.007(5) 0.042(6) O2X 0.109(7) 0.117(7) 0.049(5) 0.013(5) -0.020(5) 0.036(6) C1S 0.028(2) 0.058(3) 0.031(2) 0.000(2) -0.0080(17) 0.0093(19) C2S 0.0241(18) 0.049(2) 0.031(2) -0.0054(18) 0.0008(16) 0.0107(17) C3S 0.0216(19) 0.0250(18) 0.0311(19) 0.0019(15) 0.0005(15) 0.0034(15) C4S 0.0237(18) 0.035(2) 0.031(2) -0.0045(17) -0.0046(16) 0.0035(16) C5S 0.028(2) 0.036(2) 0.036(2) -0.0058(18) 0.0034(17) 0.0076(17) C6S 0.036(2) 0.078(3) 0.036(2) -0.002(2) 0.0081(19) -0.028(2) C7S 0.037(2) 0.065(3) 0.032(2) -0.003(2) -0.0049(18) -0.022(2) C8S 0.024(2) 0.0285(19) 0.031(2) 0.0027(16) -0.0025(15) -0.0047(15) C9S 0.024(2) 0.066(3) 0.038(2) -0.011(2) 0.0019(18) -0.012(2) C10S 0.031(2) 0.072(3) 0.035(2) -0.014(2) -0.0046(18) -0.014(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 N1 C5S 1.327(5) . ? N1 C1S 1.340(5) . ? N2 C6S 1.314(5) . ? N2 C10S 1.326(5) . ? O1 C1 1.316(5) . ? O2 C1 1.214(5) . ? O3 C9 1.319(5) . ? O4 C9 1.213(5) . ? C1 C22 1.472(4) . ? C1 C2 1.545(4) . ? C9 C30 1.458(4) . ? C9 C10 1.546(4) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C8 1.5096 . ? C5 C28 1.7968 . ? C6 C7 1.3900 . ? C10 C11 1.3900 . ? C10 C15 1.3901 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3901 . ? C13 C16 1.5192 . ? C13 C36 1.7248 . ? C14 C15 1.3899 . ? C22 C23 1.3900 . ? C22 C27 1.3901 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C25 C28 1.5383 . ? C25 C8 1.8844 . ? C26 C27 1.3900 . ? C30 C35 1.3900 . ? C30 C31 1.3900 . ? C31 C32 1.3900 . ? C32 C33 1.3900 . ? C33 C34 1.3900 . ? C33 C36 1.5311 . ? C33 C16 1.8367 . ? C34 C35 1.3900 . ? C8 C36 1.1221 . ? C8 C28 1.2992 . ? C8 C16 1.451(3) 4_556 ? C8 C16 1.5602 . ? C8 C28 1.593(3) 4_556 ? C8 C8 1.790(5) 4_556 ? C16 C28 1.0929 . ? C16 C36 1.1869 . ? C16 C8 1.451(3) 4_556 ? C16 C36 1.587(3) 4_556 ? C16 C16 1.708(5) 4_556 ? C28 C36 1.5600 . ? C28 C8 1.593(3) 4_556 ? C36 C16 1.587(3) 4_556 ? C1X O1X 1.234(8) . ? C1X N1X 1.334(9) . ? C2X N1X 1.442(9) . ? C3X N1X 1.453(8) . ? C4X O2X 1.233(8) . ? C4X N2X 1.323(8) . ? C5X N2X 1.441(10) . ? C6X N2X 1.414(9) . ? C1S C2S 1.376(5) . ? C2S C3S 1.394(5) . ? C3S C4S 1.395(5) . ? C3S C3S 1.487(7) 2_565 ? C4S C5S 1.380(5) . ? C6S C7S 1.380(6) . ? C7S C8S 1.390(6) . ? C8S C9S 1.378(5) . ? C8S C8S 1.492(7) 5_565 ? C9S C10S 1.379(5) . ? 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 C5S N1 C1S 117.2(3) . . ? C6S N2 C10S 116.2(3) . . ? O2 C1 O1 123.4(4) . . ? O2 C1 C22 115.6(4) . . ? O1 C1 C22 120.8(3) . . ? O2 C1 C2 128.9(4) . . ? O1 C1 C2 107.5(3) . . ? C22 C1 C2 15.8 . . ? O4 C9 O3 122.4(4) . . ? O4 C9 C30 116.8(4) . . ? O3 C9 C30 120.5(4) . . ? O4 C9 C10 129.4(4) . . ? O3 C9 C10 108.1(3) . . ? C30 C9 C10 14.9 . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 116.6(2) . . ? C7 C2 C1 123.2(2) . . ? C2 C3 C4 120.0 . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 C8 124.1 . . ? C6 C5 C8 115.8 . . ? C4 C5 C28 79.1 . . ? C6 C5 C28 160.9 . . ? C8 C5 C28 45.2 . . ? C7 C6 C5 120.0 . . ? C6 C7 C2 120.0 . . ? C11 C10 C15 120.0 . . ? C11 C10 C9 116.4(2) . . ? C15 C10 C9 123.1(2) . . ? C12 C11 C10 120.0 . . ? C13 C12 C11 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 C16 123.4 . . ? C14 C13 C16 116.3 . . ? C12 C13 C36 82.2 . . ? C14 C13 C36 157.5 . . ? C16 C13 C36 42.3 . . ? C15 C14 C13 120.0 . . ? C14 C15 C10 120.0 . . ? C23 C22 C27 120.0 . . ? C23 C22 C1 120.3(2) . . ? C27 C22 C1 119.5(2) . . ? C22 C23 C24 120.0 . . ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 C28 116.2 . . ? C26 C25 C28 123.6 . . ? C24 C25 C8 159.4 . . ? C26 C25 C8 80.5 . . ? C28 C25 C8 43.2 . . ? C27 C26 C25 120.0 . . ? C26 C27 C22 120.0 . . ? C35 C30 C31 120.0 . . ? C35 C30 C9 119.1(2) . . ? C31 C30 C9 120.7(2) . . ? C32 C31 C30 120.0 . . ? C31 C32 C33 120.0 . . ? C34 C33 C32 120.0 . . ? C34 C33 C36 123.7 . . ? C32 C33 C36 116.2 . . ? C34 C33 C16 84.7 . . ? C32 C33 C16 154.7 . . ? C36 C33 C16 40.0 . . ? C33 C34 C35 120.0 . . ? C34 C35 C30 120.0 . . ? C36 C8 C28 79.9 . . ? C36 C8 C16 74.96(7) . 4_556 ? C28 C8 C16 106.7(3) . 4_556 ? C36 C8 C5 126.1 . . ? C28 C8 C5 79.2 . . ? C16 C8 C5 158.88(7) 4_556 . ? C36 C8 C16 49.3 . . ? C28 C8 C16 43.8 . . ? C16 C8 C16 69.0(2) 4_556 . ? C5 C8 C16 122.2 . . ? C36 C8 C28 115.37(7) . 4_556 ? C28 C8 C28 103.0(3) . 4_556 ? C16 C8 C28 41.76(9) 4_556 4_556 ? C5 C8 C28 117.5 . 4_556 ? C16 C8 C28 88.9(2) . 4_556 ? C36 C8 C8 95.80(8) . 4_556 ? C28 C8 C8 59.6(2) . 4_556 ? C16 C8 C8 56.40(16) 4_556 4_556 ? C5 C8 C8 114.44(8) . 4_556 ? C16 C8 C8 50.78(15) . 4_556 ? C28 C8 C8 44.71(12) 4_556 4_556 ? C36 C8 C25 119.3 . . ? C28 C8 C25 54.1 . . ? C16 C8 C25 148.1(2) 4_556 . ? C5 C8 C25 26.1 . . ? C16 C8 C25 97.8 . . ? C28 C8 C25 112.17(12) 4_556 . ? C8 C8 C25 92.42(13) 4_556 . ? C28 C16 C36 86.3 . . ? C28 C16 C8 76.07(7) . 4_556 ? C36 C16 C8 113.1(3) . 4_556 ? C28 C16 C13 125.4 . . ? C36 C16 C13 78.1 . . ? C8 C16 C13 157.52(9) 4_556 . ? C28 C16 C8 55.3 . . ? C36 C16 C8 45.8 . . ? C8 C16 C8 72.8(2) 4_556 . ? C13 C16 C8 123.2 . . ? C28 C16 C36 117.7 . 4_556 ? C36 C16 C36 103.8(3) . 4_556 ? C8 C16 C36 43.05(9) 4_556 4_556 ? C13 C16 C36 116.8 . 4_556 ? C8 C16 C36 89.0(2) . 4_556 ? C28 C16 C16 101.85(7) . 4_556 ? C36 C16 C16 63.5(2) . 4_556 ? C8 C16 C16 58.51(15) 4_556 4_556 ? C13 C16 C16 116.17(8) . 4_556 ? C8 C16 C16 52.47(16) . 4_556 ? C36 C16 C16 42.02(11) 4_556 4_556 ? C28 C16 C33 123.5 . . ? C36 C16 C33 56.0 . . ? C8 C16 C33 152.9(2) 4_556 . ? C13 C16 C33 23.3 . . ? C8 C16 C33 101.7 . . ? C36 C16 C33 111.69(10) 4_556 . ? C16 C16 C33 96.64(12) 4_556 . ? C16 C28 C8 80.9 . . ? C16 C28 C25 163.5 . . ? C8 C28 C25 82.8 . . ? C16 C28 C36 49.4 . . ? C8 C28 C36 45.1 . . ? C25 C28 C36 115.7 . . ? C16 C28 C8 62.2 . 4_556 ? C8 C28 C8 75.7(3) . 4_556 ? C25 C28 C8 115.84(10) . 4_556 ? C36 C28 C8 88.82(17) . 4_556 ? C16 C28 C5 135.4 . . ? C8 C28 C5 55.6 . . ? C25 C28 C5 28.1 . . ? C36 C28 C5 88.7 . . ? C8 C28 C5 109.9(2) 4_556 . ? C8 C36 C16 85.0 . . ? C8 C36 C33 168.8 . . ? C16 C36 C33 84.0 . . ? C8 C36 C28 55.1 . . ? C16 C36 C28 44.4 . . ? C33 C36 C28 114.8 . . ? C8 C36 C16 62.0 . 4_556 ? C16 C36 C16 74.4(3) . 4_556 ? C33 C36 C16 116.30(10) . 4_556 ? C28 C36 C16 89.14(18) . 4_556 ? C8 C36 C13 143.3 . . ? C16 C36 C13 59.5 . . ? C33 C36 C13 25.6 . . ? C28 C36 C13 90.2 . . ? C16 C36 C13 111.7(2) 4_556 . ? O1X C1X N1X 124.6(10) . . ? C1X N1X C2X 119.1(10) . . ? C1X N1X C3X 121.8(10) . . ? C2X N1X C3X 119.1(11) . . ? O2X C4X N2X 126.9(10) . . ? C4X N2X C6X 125.3(11) . . ? C4X N2X C5X 111.9(12) . . ? C6X N2X C5X 122.7(12) . . ? N1 C1S C2S 123.6(4) . . ? C1S C2S C3S 118.9(4) . . ? C2S C3S C4S 117.5(3) . . ? C2S C3S C3S 120.4(2) . 2_565 ? C4S C3S C3S 122.1(2) . 2_565 ? C5S C4S C3S 119.1(3) . . ? N1 C5S C4S 123.6(4) . . ? N2 C6S C7S 124.7(4) . . ? C6S C7S C8S 119.0(4) . . ? C9S C8S C7S 116.4(3) . . ? C9S C8S C8S 122.0(4) . 5_565 ? C7S C8S C8S 121.6(4) . 5_565 ? C8S C9S C10S 119.9(4) . . ? N2 C10S C9S 123.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.84 1.85 2.683(4) 174.4 5_566 O3 H3 N2 0.84 1.84 2.673(4) 175.0 5_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.353 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.059 data_A524jj _database_code_depnum_ccdc_archive 'CCDC 873783' #TrackingRef '- GK8CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H56 N4 O11' _chemical_formula_weight 913.01 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 C2/c 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' '-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 28.787(3) _cell_length_b 10.7716(12) _cell_length_c 14.7431(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.240(3) _cell_angle_gamma 90.00 _cell_volume 4552.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 691 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.57 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9458 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15946 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5201 _reflns_number_gt 3633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The top electron density of 0.67 e/Ang3 is close to C22 by 0.72 Ang. This information is added as requested by the referee no. 3. ; _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^)+(0.0828P)^2^+7.9035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5201 _refine_ls_number_parameters 312 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1995 _refine_ls_wR_factor_gt 0.1804 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.111 _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 0.36199(8) -0.0184(2) 0.13099(14) 0.0354(5) Uani 1 1 d . . . H1 H 0.3777 -0.0285 0.0863 0.053 Uiso 1 1 calc R . . O2 O 0.32561(7) 0.1246(2) 0.04120(13) 0.0344(5) Uani 1 1 d . . . O3 O 0.46723(7) 0.4934(2) 0.38917(15) 0.0405(6) Uani 1 1 d . . . H3 H 0.4917 0.5306 0.3780 0.061 Uiso 1 1 calc R . . O4 O 0.44271(8) 0.6853(2) 0.41658(17) 0.0477(6) Uani 1 1 d . . . O5 O 0.45456(7) 0.5879(2) 0.15226(15) 0.0417(6) Uani 1 1 d . . . N1 N 0.41678(8) 0.9450(2) 1.00627(15) 0.0239(5) Uani 1 1 d . . . N2 N 0.38319(8) 0.5648(2) 0.19930(16) 0.0302(6) Uani 1 1 d . . . C1 C 0.23911(9) 0.2316(2) 0.42758(16) 0.0187(5) Uani 1 1 d . . . H1A H 0.2058 0.2496 0.4061 0.022 Uiso 1 1 calc R . . C2 C 0.25986(9) 0.3479(2) 0.48371(16) 0.0183(5) Uani 1 1 d . . . H2 H 0.2356 0.4141 0.4846 0.022 Uiso 1 1 calc R . . C3 C 0.26336(8) 0.1839(2) 0.34759(16) 0.0182(5) Uani 1 1 d . . . C4 C 0.29057(9) 0.0776(3) 0.35060(18) 0.0221(6) Uani 1 1 d . . . H4 H 0.2939 0.0292 0.4047 0.026 Uiso 1 1 calc R . . C5 C 0.31306(9) 0.0407(3) 0.27525(18) 0.0235(6) Uani 1 1 d . . . H5 H 0.3321 -0.0314 0.2787 0.028 Uiso 1 1 calc R . . C6 C 0.30768(9) 0.1092(2) 0.19509(17) 0.0204(6) Uani 1 1 d . . . C7 C 0.27929(9) 0.2138(2) 0.19071(18) 0.0225(6) Uani 1 1 d . . . H7 H 0.2747 0.2599 0.1357 0.027 Uiso 1 1 calc R . . C8 C 0.25766(9) 0.2512(3) 0.26608(18) 0.0225(6) Uani 1 1 d . . . H8 H 0.2387 0.3235 0.2625 0.027 Uiso 1 1 calc R . . C9 C 0.33287(9) 0.0727(3) 0.11423(18) 0.0235(6) Uani 1 1 d . . . C10 C 0.30562(9) 0.4045(2) 0.46377(16) 0.0181(5) Uani 1 1 d . . . C11 C 0.34532(9) 0.3320(3) 0.45422(17) 0.0210(6) Uani 1 1 d . . . H11 H 0.3435 0.2443 0.4597 0.025 Uiso 1 1 calc R . . C12 C 0.38701(9) 0.3864(3) 0.43688(17) 0.0232(6) Uani 1 1 d . . . H12 H 0.4133 0.3358 0.4286 0.028 Uiso 1 1 calc R . . C13 C 0.39081(9) 0.5150(3) 0.43146(17) 0.0239(6) Uani 1 1 d . . . C14 C 0.35238(10) 0.5880(3) 0.44355(18) 0.0257(6) Uani 1 1 d . . . H14 H 0.3550 0.6759 0.4419 0.031 Uiso 1 1 calc R . . C15 C 0.31009(9) 0.5334(3) 0.45807(17) 0.0225(6) Uani 1 1 d . . . H15 H 0.2837 0.5845 0.4643 0.027 Uiso 1 1 calc R . . C16 C 0.43596(10) 0.5754(3) 0.41234(19) 0.0337(7) Uani 1 1 d . . . C23 C 0.42219(12) 0.5183(3) 0.1712(2) 0.0381(8) Uani 1 1 d . . . C24 C 0.42647(16) 0.3780(4) 0.1656(3) 0.0587(12) Uani 1 1 d . . . H24A H 0.4562 0.3564 0.1422 0.088 Uiso 1 1 calc R . . H24B H 0.4007 0.3450 0.1245 0.088 Uiso 1 1 calc R . . H24C H 0.4253 0.3420 0.2263 0.088 Uiso 1 1 calc R . . C25 C 0.34209(11) 0.4899(3) 0.2109(2) 0.0334(7) Uani 1 1 d . . . H25A H 0.3245 0.4768 0.1516 0.050 Uiso 1 1 calc R . . H25B H 0.3223 0.5329 0.2516 0.050 Uiso 1 1 calc R . . H25C H 0.3517 0.4095 0.2375 0.050 Uiso 1 1 calc R . . C26 C 0.37989(10) 0.7001(3) 0.2062(2) 0.0292(6) Uani 1 1 d . . . H26A H 0.4096 0.7335 0.2335 0.044 Uiso 1 1 calc R . . H26B H 0.3550 0.7219 0.2445 0.044 Uiso 1 1 calc R . . H26C H 0.3728 0.7356 0.1453 0.044 Uiso 1 1 calc R . . C17 C 0.41080(10) 1.0172(3) 0.93275(19) 0.0300(7) Uani 1 1 d . . . H17 H 0.3855 1.0740 0.9275 0.036 Uiso 1 1 calc R . . C18 C 0.44021(12) 1.0122(3) 0.8640(2) 0.0423(9) Uani 1 1 d . . . H18 H 0.4353 1.0661 0.8130 0.051 Uiso 1 1 calc R . . C19 C 0.47686(11) 0.9284(3) 0.86949(19) 0.0318(7) Uani 1 1 d . . . C20 C 0.48321(10) 0.8545(3) 0.94653(17) 0.0232(6) Uani 1 1 d . . . H20 H 0.5083 0.7971 0.9536 0.028 Uiso 1 1 calc R . . C21 C 0.45270(10) 0.8655(3) 1.01270(18) 0.0261(6) Uani 1 1 d . . . H21 H 0.4573 0.8144 1.0653 0.031 Uiso 1 1 calc R . . C22 C 0.51086(13) 0.9235(4) 0.7976(2) 0.0523(10) Uani 1 1 d U . . H22A H 0.5320 0.9958 0.8059 0.063 Uiso 1 1 calc R . . H22B H 0.5301 0.8476 0.8073 0.063 Uiso 1 1 calc R . . O1W O 0.5000 0.7893(6) 0.2500 0.129(2) Uani 1 2 d SD . . H1WA H 0.515(2) 0.733(3) 0.288(3) 0.120 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 0.0469(13) 0.0349(12) 0.0288(11) 0.0053(9) 0.0266(10) 0.0116(10) O2 0.0395(12) 0.0451(13) 0.0210(10) 0.0007(9) 0.0147(9) 0.0062(10) O3 0.0201(11) 0.0649(16) 0.0379(13) -0.0017(11) 0.0104(9) -0.0172(11) O4 0.0409(14) 0.0453(15) 0.0560(16) 0.0075(12) 0.0000(11) -0.0251(12) O5 0.0226(11) 0.0677(17) 0.0365(13) 0.0083(11) 0.0122(9) 0.0116(11) N1 0.0299(12) 0.0253(12) 0.0183(11) -0.0037(9) 0.0128(9) -0.0033(10) N2 0.0268(13) 0.0390(15) 0.0251(13) 0.0007(11) 0.0035(10) 0.0056(11) C1 0.0155(12) 0.0270(14) 0.0141(12) -0.0011(10) 0.0040(9) 0.0000(10) C2 0.0179(12) 0.0233(14) 0.0147(12) -0.0019(10) 0.0066(9) 0.0019(10) C3 0.0136(11) 0.0251(14) 0.0166(12) -0.0063(10) 0.0045(9) -0.0043(10) C4 0.0232(13) 0.0267(14) 0.0171(13) -0.0003(10) 0.0064(10) -0.0026(11) C5 0.0253(14) 0.0233(14) 0.0231(14) -0.0053(11) 0.0087(11) -0.0004(11) C6 0.0208(13) 0.0232(14) 0.0183(13) -0.0072(10) 0.0089(10) -0.0070(10) C7 0.0268(14) 0.0241(14) 0.0175(13) -0.0007(10) 0.0070(10) -0.0031(11) C8 0.0226(13) 0.0256(14) 0.0204(13) -0.0020(11) 0.0073(10) 0.0009(11) C9 0.0262(14) 0.0255(14) 0.0205(13) -0.0060(11) 0.0110(11) -0.0070(12) C10 0.0179(12) 0.0263(14) 0.0107(11) -0.0016(10) 0.0042(9) -0.0012(10) C11 0.0218(13) 0.0251(14) 0.0164(12) -0.0003(10) 0.0040(10) -0.0020(11) C12 0.0196(13) 0.0335(15) 0.0170(13) 0.0001(11) 0.0045(10) -0.0015(11) C13 0.0246(14) 0.0336(16) 0.0137(12) 0.0014(11) 0.0022(10) -0.0100(12) C14 0.0327(15) 0.0235(14) 0.0209(14) -0.0003(11) 0.0027(11) -0.0066(12) C15 0.0266(14) 0.0242(14) 0.0172(13) -0.0022(10) 0.0050(10) 0.0002(11) C16 0.0281(16) 0.052(2) 0.0203(14) 0.0031(13) -0.0013(12) -0.0170(15) C23 0.0434(19) 0.053(2) 0.0183(14) 0.0038(13) 0.0026(13) 0.0181(16) C24 0.093(3) 0.046(2) 0.039(2) 0.0006(16) 0.015(2) 0.036(2) C25 0.0320(16) 0.0447(19) 0.0232(15) 0.0034(13) 0.0005(12) -0.0074(14) C26 0.0244(14) 0.0314(16) 0.0321(16) -0.0008(12) 0.0046(12) 0.0066(12) C17 0.0272(15) 0.0398(17) 0.0241(14) 0.0003(12) 0.0080(11) 0.0094(13) C18 0.0401(18) 0.061(2) 0.0289(16) 0.0198(15) 0.0190(14) 0.0252(17) C19 0.0340(16) 0.0398(18) 0.0240(15) 0.0066(12) 0.0155(12) 0.0107(13) C20 0.0269(14) 0.0239(14) 0.0200(13) -0.0019(11) 0.0088(11) 0.0033(11) C21 0.0383(16) 0.0220(14) 0.0197(13) 0.0019(11) 0.0114(12) 0.0002(12) C22 0.0507(18) 0.067(2) 0.0434(17) 0.0224(15) 0.0284(15) 0.0277(16) O1W 0.118(5) 0.091(5) 0.166(7) 0.000 -0.045(5) 0.000 _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 C9 1.299(3) . ? O1 H1 0.8400 . ? O2 C9 1.215(3) . ? O3 C16 1.328(4) . ? O3 H3 0.8400 . ? O4 C16 1.200(4) . ? O5 C23 1.248(4) . ? N1 C17 1.333(4) . ? N1 C21 1.339(4) . ? N2 C23 1.330(4) . ? N2 C25 1.455(4) . ? N2 C26 1.465(4) . ? C1 C3 1.514(3) . ? C1 C2 1.561(3) 7_556 ? C1 C2 1.587(3) . ? C1 H1A 1.0000 . ? C2 C10 1.505(3) . ? C2 C1 1.561(3) 7_556 ? C2 H2 1.0000 . ? C3 C4 1.386(4) . ? C3 C8 1.400(4) . ? C4 C5 1.394(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.390(4) . ? C6 C9 1.503(3) . ? C7 C8 1.382(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 C15 1.397(4) . ? C10 C11 1.402(4) . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 C13 1.392(4) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 C16 1.503(4) . ? C14 C15 1.386(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C23 C24 1.519(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C17 C18 1.380(4) . ? C17 H17 0.9500 . ? C18 C19 1.385(4) . ? C18 H18 0.9500 . ? C19 C20 1.385(4) . ? C19 C22 1.508(4) . ? C20 C21 1.376(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C22 1.484(8) 2_656 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O1W H1WA 0.9003(11) . ? 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 C9 O1 H1 109.5 . . ? C16 O3 H3 109.5 . . ? C17 N1 C21 118.2(2) . . ? C23 N2 C25 123.1(3) . . ? C23 N2 C26 117.3(3) . . ? C25 N2 C26 119.0(2) . . ? C3 C1 C2 119.4(2) . 7_556 ? C3 C1 C2 119.7(2) . . ? C2 C1 C2 91.05(19) 7_556 . ? C3 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 7_556 . ? C2 C1 H1A 108.4 . . ? C10 C2 C1 115.9(2) . 7_556 ? C10 C2 C1 120.8(2) . . ? C1 C2 C1 88.95(18) 7_556 . ? C10 C2 H2 109.8 . . ? C1 C2 H2 109.8 7_556 . ? C1 C2 H2 109.8 . . ? C4 C3 C8 118.5(2) . . ? C4 C3 C1 123.7(2) . . ? C8 C3 C1 117.8(2) . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 C9 120.7(2) . . ? C7 C6 C9 120.0(2) . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C3 120.8(2) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? O2 C9 O1 124.9(2) . . ? O2 C9 C6 121.7(3) . . ? O1 C9 C6 113.3(2) . . ? C15 C10 C11 117.9(2) . . ? C15 C10 C2 120.1(2) . . ? C11 C10 C2 122.0(2) . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.4(2) . . ? C14 C13 C16 119.6(3) . . ? C12 C13 C16 121.0(3) . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C10 121.2(3) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? O4 C16 O3 124.0(3) . . ? O4 C16 C13 123.8(3) . . ? O3 C16 C13 112.2(3) . . ? O5 C23 N2 120.8(3) . . ? O5 C23 C24 121.3(3) . . ? N2 C23 C24 117.8(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 C17 C18 122.1(3) . . ? N1 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 117.7(3) . . ? C18 C19 C22 121.4(3) . . ? C20 C19 C22 120.7(3) . . ? C21 C20 C19 119.2(3) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? N1 C21 C20 122.9(2) . . ? N1 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C22 C22 C19 114.9(4) 2_656 . ? C22 C22 H22A 108.5 2_656 . ? C19 C22 H22A 108.5 . . ? C22 C22 H22B 108.5 2_656 . ? C19 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.84 1.73 2.560(3) 171.5 1_544 O3 H3 O5 0.84 1.76 2.594(3) 171.6 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.673 _refine_diff_density_min -0.814 _refine_diff_density_rms 0.074