# Electronic Supplementary Material (ESI) for Chemical Science # 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_zwi_172c_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 N O4' _chemical_formula_sum 'C19 H25 N O4' _chemical_formula_weight 331.40 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3357(13) _cell_length_b 11.294(2) _cell_length_c 9.9646(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.551(8) _cell_angle_gamma 90.00 _cell_volume 912.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8404 _cell_measurement_theta_min 4.56 _cell_measurement_theta_max 65.57 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.683 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5359 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Microstar CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10439 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 66.25 _reflns_number_total 3021 _reflns_number_gt 2861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0878P)^2^+0.1407P] 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 0.2(2) _refine_ls_number_reflns 3021 _refine_ls_number_parameters 248 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.004 _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 0.5465(2) 0.27956(18) 0.9697(2) 0.0236(4) Uani 1 1 d . . . H1N H 0.490(4) 0.300(3) 1.036(3) 0.033(7) Uiso 1 1 d . . . O1 O 1.33844(17) 0.34980(14) 1.15511(17) 0.0245(4) Uani 1 1 d . . . H1 H 1.3333 0.4181 1.1873 0.037 Uiso 1 1 calc R . . O2 O 0.56702(19) 0.46162(14) 0.87066(19) 0.0288(4) Uani 1 1 d . . . O3 O 0.69336(18) 0.07168(14) 0.76387(16) 0.0246(4) Uani 1 1 d . . . O4 O 0.6897(2) 0.45012(15) 0.65460(19) 0.0308(4) Uani 1 1 d . . . H4 H 0.6460 0.4792 0.7150 0.046 Uiso 1 1 calc R . . C1 C 1.1886(2) 0.2945(2) 1.1397(2) 0.0207(5) Uani 1 1 d . . . C2 C 1.1734(3) 0.1800(2) 1.0869(2) 0.0248(5) Uani 1 1 d . . . H2 H 1.2653 0.1423 1.0640 0.030 Uiso 1 1 calc R . . C3 C 1.0236(3) 0.1209(2) 1.0678(2) 0.0237(5) Uani 1 1 d . . . H3 H 1.0145 0.0428 1.0314 0.028 Uiso 1 1 calc R . . C4 C 0.8866(3) 0.1732(2) 1.1005(2) 0.0218(5) Uani 1 1 d . . . C5 C 0.9059(2) 0.2876(2) 1.1558(2) 0.0218(5) Uani 1 1 d . . . H5 H 0.8150 0.3250 1.1808 0.026 Uiso 1 1 calc R . . C6 C 1.0546(3) 0.3477(2) 1.1749(2) 0.0217(5) Uani 1 1 d . . . H6 H 1.0645 0.4255 1.2122 0.026 Uiso 1 1 calc R . . C7 C 0.7233(3) 0.1091(2) 1.0759(2) 0.0238(5) Uani 1 1 d . . . H7A H 0.6802 0.1154 1.1602 0.029 Uiso 1 1 calc R . . H7B H 0.7422 0.0241 1.0607 0.029 Uiso 1 1 calc R . . C8 C 0.5914(2) 0.1558(2) 0.9526(2) 0.0218(5) Uani 1 1 d . . . H8 H 0.4908 0.1048 0.9379 0.026 Uiso 1 1 calc R . . C9 C 0.6539(2) 0.1605(2) 0.8205(2) 0.0207(5) Uani 1 1 d . . . C10 C 0.6551(2) 0.2827(2) 0.7809(2) 0.0209(5) Uani 1 1 d . . . C11 C 0.5869(2) 0.3518(2) 0.8763(2) 0.0222(5) Uani 1 1 d . . . C12 C 0.7041(2) 0.3350(2) 0.6721(2) 0.0228(5) Uani 1 1 d . . . C13 C 0.7668(3) 0.2687(2) 0.5653(2) 0.0255(5) Uani 1 1 d . B . H13 H 0.8079 0.1899 0.6048 0.031 Uiso 1 1 calc R . . C14 C 0.6208(3) 0.2473(3) 0.4410(3) 0.0411(7) Uani 1 1 d . . . H14A H 0.5364 0.2001 0.4703 0.062 Uiso 1 1 calc R . . H14B H 0.6595 0.2046 0.3689 0.062 Uiso 1 1 calc R . . H14C H 0.5736 0.3235 0.4046 0.062 Uiso 1 1 calc R . . C15 C 0.9092(3) 0.3322(2) 0.5225(2) 0.0283(5) Uani 1 1 d . . . H15A H 0.9470 0.2816 0.4548 0.034 Uiso 1 1 calc R A 1 H15B H 0.8658 0.4063 0.4745 0.034 Uiso 1 1 calc R A 1 C16A C 1.0592(3) 0.3633(2) 0.6382(3) 0.0304(6) Uani 0.82(2) 1 d PD B 1 H16A H 1.0208 0.4253 0.6951 0.037 Uiso 0.82(2) 1 calc PR B 1 C17A C 1.1914(3) 0.4219(3) 0.5782(3) 0.0453(7) Uani 0.82(2) 1 d P B 1 H17A H 1.2867 0.4417 0.6531 0.068 Uiso 0.82(2) 1 calc PR B 1 H17B H 1.1468 0.4943 0.5293 0.068 Uiso 0.82(2) 1 calc PR B 1 H17C H 1.2257 0.3673 0.5137 0.068 Uiso 0.82(2) 1 calc PR B 1 C18A C 1.1252(5) 0.2626(6) 0.7363(8) 0.0383(14) Uani 0.82(2) 1 d PD B 1 H18A H 1.2167 0.2933 0.8102 0.046 Uiso 0.82(2) 1 calc PR B 1 H18B H 1.0366 0.2361 0.7804 0.046 Uiso 0.82(2) 1 calc PR B 1 C19A C 1.1866(7) 0.1571(5) 0.6712(10) 0.057(2) Uani 0.82(2) 1 d PD B 1 H19A H 1.0987 0.1277 0.5952 0.086 Uiso 0.82(2) 1 calc PR B 1 H19B H 1.2192 0.0945 0.7404 0.086 Uiso 0.82(2) 1 calc PR B 1 H19C H 1.2821 0.1802 0.6355 0.086 Uiso 0.82(2) 1 calc PR B 1 C16B C 1.0592(3) 0.3633(2) 0.6382(3) 0.0304(6) Uani 0.18(2) 1 d PD B 2 H16B H 1.0312 0.4086 0.7158 0.037 Uiso 0.18(2) 1 calc PR B 2 C17B C 1.1914(3) 0.4219(3) 0.5782(3) 0.0453(7) Uani 0.18(2) 1 d P B 2 H17D H 1.2974 0.3822 0.6138 0.068 Uiso 0.18(2) 1 calc PR B 2 H17E H 1.2010 0.5055 0.6049 0.068 Uiso 0.18(2) 1 calc PR B 2 H17F H 1.1608 0.4156 0.4773 0.068 Uiso 0.18(2) 1 calc PR B 2 C18B C 1.144(3) 0.2409(15) 0.683(3) 0.040(6) Uani 0.18(2) 1 d PD B 2 H18C H 1.2349 0.2559 0.7649 0.048 Uiso 0.18(2) 1 calc PR B 2 H18D H 1.0621 0.1912 0.7143 0.048 Uiso 0.18(2) 1 calc PR B 2 C19B C 1.214(3) 0.167(3) 0.586(5) 0.062(10) Uani 0.18(2) 1 d PD B 2 H19D H 1.1245 0.1390 0.5107 0.094 Uiso 0.18(2) 1 calc PR B 2 H19E H 1.2719 0.0987 0.6363 0.094 Uiso 0.18(2) 1 calc PR B 2 H19F H 1.2917 0.2143 0.5487 0.094 Uiso 0.18(2) 1 calc PR B 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 N1 0.0199(8) 0.0215(10) 0.0329(11) -0.0039(8) 0.0134(8) -0.0002(7) O1 0.0194(7) 0.0207(8) 0.0363(9) -0.0031(7) 0.0122(6) -0.0016(6) O2 0.0247(8) 0.0184(8) 0.0466(11) -0.0038(7) 0.0153(7) 0.0022(6) O3 0.0263(8) 0.0200(8) 0.0298(9) -0.0018(7) 0.0116(6) 0.0040(6) O4 0.0358(9) 0.0196(9) 0.0403(10) 0.0045(7) 0.0158(8) 0.0038(7) C1 0.0183(10) 0.0204(12) 0.0246(11) 0.0026(8) 0.0072(8) -0.0020(8) C2 0.0223(10) 0.0216(12) 0.0335(12) -0.0015(10) 0.0124(9) 0.0034(9) C3 0.0269(11) 0.0184(11) 0.0270(12) 0.0009(9) 0.0086(9) 0.0006(9) C4 0.0242(11) 0.0214(11) 0.0217(10) 0.0028(9) 0.0090(8) -0.0028(9) C5 0.0194(10) 0.0246(12) 0.0232(11) -0.0028(9) 0.0088(8) 0.0011(9) C6 0.0245(11) 0.0194(11) 0.0237(10) 0.0015(9) 0.0104(9) 0.0008(8) C7 0.0237(11) 0.0232(11) 0.0272(12) 0.0019(9) 0.0113(9) -0.0050(9) C8 0.0181(10) 0.0184(11) 0.0312(12) -0.0042(9) 0.0108(9) -0.0031(8) C9 0.0127(9) 0.0219(12) 0.0270(11) 0.0005(9) 0.0037(8) -0.0002(8) C10 0.0157(9) 0.0196(12) 0.0277(12) -0.0009(9) 0.0061(8) 0.0019(8) C11 0.0126(9) 0.0243(13) 0.0306(12) -0.0017(9) 0.0070(8) 0.0003(8) C12 0.0178(9) 0.0208(12) 0.0295(12) 0.0020(9) 0.0050(8) 0.0007(8) C13 0.0267(11) 0.0275(12) 0.0239(11) 0.0006(10) 0.0088(9) 0.0019(9) C14 0.0346(14) 0.057(2) 0.0320(14) -0.0101(13) 0.0085(11) -0.0079(12) C15 0.0273(11) 0.0340(14) 0.0253(11) 0.0041(10) 0.0098(9) 0.0009(10) C16A 0.0274(12) 0.0348(14) 0.0309(13) -0.0037(10) 0.0106(10) -0.0007(10) C17A 0.0349(14) 0.0469(19) 0.0528(18) 0.0054(14) 0.0078(13) -0.0129(13) C18A 0.0244(18) 0.054(3) 0.032(3) 0.011(3) -0.0012(18) -0.0057(17) C19A 0.038(2) 0.039(3) 0.084(5) 0.003(3) -0.007(3) 0.0036(18) C16B 0.0274(12) 0.0348(14) 0.0309(13) -0.0037(10) 0.0106(10) -0.0007(10) C17B 0.0349(14) 0.0469(19) 0.0528(18) 0.0054(14) 0.0078(13) -0.0129(13) C18B 0.035(10) 0.059(16) 0.027(13) -0.022(10) 0.010(9) -0.022(10) C19B 0.045(11) 0.040(12) 0.10(3) -0.021(15) 0.015(13) 0.010(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 N1 C11 1.338(3) . ? N1 C8 1.468(3) . ? N1 H1N 0.92(3) . ? O1 C1 1.373(3) . ? O1 H1 0.8400 . ? O2 C11 1.251(3) . ? O3 C9 1.232(3) . ? O4 C12 1.314(3) . ? O4 H4 0.8400 . ? C1 C6 1.384(3) . ? C1 C2 1.391(3) . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.398(3) . ? C4 C7 1.511(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.537(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.526(3) . ? C8 H8 1.0000 . ? C9 C10 1.436(3) . ? C10 C12 1.378(3) . ? C10 C11 1.446(3) . ? C12 C13 1.493(3) . ? C13 C15 1.530(3) . ? C13 C14 1.538(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16A 1.530(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16A C18A 1.516(5) . ? C16A C17A 1.522(4) . ? C16A H16A 1.0000 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A C19A 1.503(7) . ? C18A H18A 0.9900 . ? C18A H18B 0.9900 . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C18B C19B 1.492(19) . ? C18B H18C 0.9900 . ? C18B H18D 0.9900 . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C8 112.79(18) . . ? C11 N1 H1N 126.9(19) . . ? C8 N1 H1N 120.2(19) . . ? C1 O1 H1 109.5 . . ? C12 O4 H4 109.5 . . ? O1 C1 C6 122.8(2) . . ? O1 C1 C2 117.70(17) . . ? C6 C1 C2 119.50(19) . . ? C3 C2 C1 119.85(19) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.7(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 117.39(19) . . ? C3 C4 C7 121.1(2) . . ? C5 C4 C7 121.51(19) . . ? C6 C5 C4 121.49(19) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C1 C6 C5 120.1(2) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C4 C7 C8 114.41(18) . . ? C4 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C4 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C9 102.42(18) . . ? N1 C8 C7 112.85(18) . . ? C9 C8 C7 112.15(17) . . ? N1 C8 H8 109.7 . . ? C9 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? O3 C9 C10 129.5(2) . . ? O3 C9 C8 123.2(2) . . ? C10 C9 C8 107.22(17) . . ? C12 C10 C9 130.6(2) . . ? C12 C10 C11 121.4(2) . . ? C9 C10 C11 108.01(18) . . ? O2 C11 N1 125.7(2) . . ? O2 C11 C10 125.0(2) . . ? N1 C11 C10 109.26(19) . . ? O4 C12 C10 119.6(2) . . ? O4 C12 C13 116.0(2) . . ? C10 C12 C13 124.3(2) . . ? C12 C13 C15 112.8(2) . . ? C12 C13 C14 108.0(2) . . ? C15 C13 C14 111.6(2) . . ? C12 C13 H13 108.1 . . ? C15 C13 H13 108.1 . . ? C14 C13 H13 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16A C15 C13 116.61(19) . . ? C16A C15 H15A 108.1 . . ? C13 C15 H15A 108.1 . . ? C16A C15 H15B 108.1 . . ? C13 C15 H15B 108.1 . . ? H15A C15 H15B 107.3 . . ? C18A C16A C17A 113.1(3) . . ? C18A C16A C15 115.0(3) . . ? C17A C16A C15 110.1(2) . . ? C18A C16A H16A 106.0 . . ? C17A C16A H16A 106.0 . . ? C15 C16A H16A 106.0 . . ? C19A C18A C16A 115.1(4) . . ? C19A C18A H18A 108.5 . . ? C16A C18A H18A 108.5 . . ? C19A C18A H18B 108.5 . . ? C16A C18A H18B 108.5 . . ? H18A C18A H18B 107.5 . . ? C19B C18B H18C 106.8 . . ? C19B C18B H18D 106.8 . . ? H18C C18B H18D 106.7 . . ? C18B C19B H19D 109.5 . . ? C18B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C18B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.2(2) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C2 C3 C4 C7 178.5(2) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C7 C4 C5 C6 -178.2(2) . . . . ? O1 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C3 C4 C7 C8 -106.2(2) . . . . ? C5 C4 C7 C8 73.3(3) . . . . ? C11 N1 C8 C9 -5.3(2) . . . . ? C11 N1 C8 C7 115.4(2) . . . . ? C4 C7 C8 N1 -62.2(2) . . . . ? C4 C7 C8 C9 52.9(3) . . . . ? N1 C8 C9 O3 -174.56(18) . . . . ? C7 C8 C9 O3 64.2(3) . . . . ? N1 C8 C9 C10 5.2(2) . . . . ? C7 C8 C9 C10 -116.02(19) . . . . ? O3 C9 C10 C12 -2.0(4) . . . . ? C8 C9 C10 C12 178.3(2) . . . . ? O3 C9 C10 C11 176.2(2) . . . . ? C8 C9 C10 C11 -3.6(2) . . . . ? C8 N1 C11 O2 -177.6(2) . . . . ? C8 N1 C11 C10 3.4(2) . . . . ? C12 C10 C11 O2 -0.4(3) . . . . ? C9 C10 C11 O2 -178.7(2) . . . . ? C12 C10 C11 N1 178.66(19) . . . . ? C9 C10 C11 N1 0.3(2) . . . . ? C9 C10 C12 O4 178.3(2) . . . . ? C11 C10 C12 O4 0.4(3) . . . . ? C9 C10 C12 C13 1.4(4) . . . . ? C11 C10 C12 C13 -176.5(2) . . . . ? O4 C12 C13 C15 41.8(3) . . . . ? C10 C12 C13 C15 -141.3(2) . . . . ? O4 C12 C13 C14 -82.1(3) . . . . ? C10 C12 C13 C14 94.9(3) . . . . ? C12 C13 C15 C16A 55.6(3) . . . . ? C14 C13 C15 C16A 177.5(2) . . . . ? C13 C15 C16A C18A 48.9(5) . . . . ? C13 C15 C16A C17A 178.1(2) . . . . ? C17A C16A C18A C19A -65.7(5) . . . . ? C15 C16A C18A C19A 61.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 66.25 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.196 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 941137' ####################################################################### # # 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_zw172e_2_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N O4' _chemical_formula_sum 'C19 H23 N O4' _chemical_formula_weight 329.38 _chemical_absolute_configuration uk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 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 _symmetry_spacce_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3372(7) _cell_length_b 22.647(3) _cell_length_c 20.618(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.112(6) _cell_angle_gamma 90.00 _cell_volume 3426.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9945 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 65.42 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5994 _exptl_absorpt_correction_T_max 0.7991 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Microstar Pt 135 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 56007 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 66.19 _reflns_number_total 5995 _reflns_number_gt 5678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0742P)^2^+1.5480P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 5995 _refine_ls_number_parameters 1017 _refine_ls_number_restraints 225 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 0.4769(6) 0.5782(2) 0.9726(2) 0.0286(10) Uani 1 1 d D . . H1N H 0.4296 0.6046 0.9463 0.034 Uiso 1 1 calc RD . . O1 O 0.6107(6) 0.61607(19) 1.34524(18) 0.0354(9) Uani 1 1 d . . . H1 H 0.5472 0.5949 1.3699 0.053 Uiso 1 1 calc R . . O2 O 0.6615(6) 0.45515(17) 1.09954(17) 0.0319(9) Uani 1 1 d . . . H2 H 0.6931 0.4244 1.0797 0.048 Uiso 1 1 calc R . . O3 O 0.5644(5) 0.52665(19) 0.88457(17) 0.0336(9) Uani 1 1 d . . . O4 O 0.7234(6) 0.38766(18) 1.00906(19) 0.0381(10) Uani 1 1 d . . . C1 C 0.5878(7) 0.5980(3) 1.2827(2) 0.0256(11) Uani 1 1 d . . . C2 C 0.6342(7) 0.6389(3) 1.2336(2) 0.0273(11) Uani 1 1 d . . . H2A H 0.6760 0.6773 1.2447 0.033 Uiso 1 1 calc R . . C3 C 0.6180(7) 0.6221(2) 1.1690(2) 0.0239(10) Uani 1 1 d . . . H3 H 0.6510 0.6493 1.1360 0.029 Uiso 1 1 calc R . . C4 C 0.5538(7) 0.5658(2) 1.1515(2) 0.0235(11) Uani 1 1 d . . . C5 C 0.5057(7) 0.5268(3) 1.2013(2) 0.0258(12) Uani 1 1 d . . . H5 H 0.4599 0.4888 1.1908 0.031 Uiso 1 1 calc R . . C6 C 0.5239(7) 0.5430(3) 1.2660(2) 0.0268(11) Uani 1 1 d . . . H6 H 0.4918 0.5158 1.2991 0.032 Uiso 1 1 calc R . . C7 C 0.4726(7) 0.5892(3) 1.0378(3) 0.0276(11) Uani 1 1 d . . . H7 H 0.4199 0.6249 1.0529 0.033 Uiso 1 1 calc R . . C8 C 0.5416(7) 0.5502(2) 1.0815(2) 0.0230(11) Uani 1 1 d . . . C9 C 0.6053(8) 0.4950(3) 1.0575(2) 0.0272(12) Uani 1 1 d . . . C10 C 0.6059(8) 0.4829(2) 0.9890(2) 0.0247(11) Uani 1 1 d . . . C11 C 0.5517(7) 0.5279(3) 0.9461(2) 0.0265(12) Uani 1 1 d . . . C12 C 0.6703(8) 0.4244(3) 0.9675(3) 0.0289(12) Uani 1 1 d . . . C13 C 0.6673(7) 0.4045(3) 0.8979(2) 0.0280(11) Uani 1 1 d . . . H13 H 0.7030 0.4385 0.8696 0.034 Uiso 1 1 calc R . . C14 C 0.4695(8) 0.3864(3) 0.8812(3) 0.0308(12) Uani 1 1 d . . . H14A H 0.4344 0.3527 0.9090 0.037 Uiso 1 1 calc R . . H14B H 0.3873 0.4197 0.8917 0.037 Uiso 1 1 calc R . . C15 C 0.4408(8) 0.3691(3) 0.8102(3) 0.0342(13) Uani 1 1 d . . . H15 H 0.5353 0.3392 0.7983 0.041 Uiso 1 1 calc R . . C16 C 0.2521(8) 0.3415(3) 0.7993(3) 0.0383(14) Uani 1 1 d . . . H16A H 0.1578 0.3706 0.8117 0.046 Uiso 1 1 calc R . . H16B H 0.2369 0.3331 0.7525 0.046 Uiso 1 1 calc R . . C17 C 0.2198(11) 0.2843(3) 0.8374(4) 0.0563(19) Uani 1 1 d . . . H17A H 0.3284 0.2593 0.8347 0.084 Uiso 1 1 calc R . . H17B H 0.1151 0.2633 0.8189 0.084 Uiso 1 1 calc R . . H17C H 0.1951 0.2939 0.8829 0.084 Uiso 1 1 calc R . . C18 C 0.8033(9) 0.3543(3) 0.8877(3) 0.0426(15) Uani 1 1 d . . . H18A H 0.7599 0.3188 0.9101 0.064 Uiso 1 1 calc R . . H18B H 0.9223 0.3658 0.9053 0.064 Uiso 1 1 calc R . . H18C H 0.8149 0.3461 0.8412 0.064 Uiso 1 1 calc R . . C19 C 0.4609(11) 0.4219(4) 0.7647(3) 0.0526(18) Uani 1 1 d . . . H19A H 0.4328 0.4096 0.7202 0.079 Uiso 1 1 calc R . . H19B H 0.5863 0.4367 0.7668 0.079 Uiso 1 1 calc R . . H19C H 0.3766 0.4532 0.7780 0.079 Uiso 1 1 calc R . . N2 N 0.0047(6) 0.5498(2) 0.2802(2) 0.0240(9) Uani 1 1 d D . . H2N H -0.0383 0.5247 0.3089 0.029 Uiso 1 1 calc RD . . O5 O 0.0763(7) 0.4991(2) -0.09309(18) 0.0455(11) Uani 1 1 d . . . H5A H 0.0727 0.5285 -0.1179 0.068 Uiso 1 1 calc R . . O6 O 0.1839(5) 0.66429(16) 0.14309(16) 0.0273(8) Uani 1 1 d . . . H6A H 0.2344 0.6936 0.1606 0.041 Uiso 1 1 calc R . . O7 O 0.2672(5) 0.73507(17) 0.22747(17) 0.0315(8) Uani 1 1 d . . . O8 O 0.1000(5) 0.60566(17) 0.36406(16) 0.0285(8) Uani 1 1 d . . . C20 C 0.0627(8) 0.5178(3) -0.0297(3) 0.0323(14) Uani 1 1 d . . . C21 C 0.1097(8) 0.4777(3) 0.0184(3) 0.0333(13) Uani 1 1 d . . . H21 H 0.1441 0.4385 0.0075 0.040 Uiso 1 1 calc R . . C22 C 0.1055(7) 0.4961(3) 0.0833(3) 0.0274(11) Uani 1 1 d . . . H22 H 0.1405 0.4693 0.1164 0.033 Uiso 1 1 calc R . . C23 C 0.0509(7) 0.5529(3) 0.1000(2) 0.0256(11) Uani 1 1 d . . . C24 C 0.0026(7) 0.5915(3) 0.0511(2) 0.0278(11) Uani 1 1 d . . . H24 H -0.0344 0.6304 0.0619 0.033 Uiso 1 1 calc R . . C25 C 0.0070(8) 0.5744(3) -0.0145(3) 0.0324(13) Uani 1 1 d . . . H25 H -0.0277 0.6013 -0.0476 0.039 Uiso 1 1 calc R . . C26 C -0.0123(7) 0.5355(3) 0.2168(2) 0.0233(11) Uani 1 1 d . . . H26 H -0.0709 0.4996 0.2050 0.028 Uiso 1 1 calc R . . C27 C 0.0544(6) 0.5723(2) 0.1688(2) 0.0214(11) Uani 1 1 d . . . C28 C 0.1251(7) 0.6271(2) 0.1892(2) 0.0242(11) Uani 1 1 d . . . C29 C 0.1397(7) 0.6431(2) 0.2552(2) 0.0228(10) Uani 1 1 d . . . C30 C 0.0835(7) 0.6003(2) 0.3031(2) 0.0244(11) Uani 1 1 d . . . C31 C 0.2134(7) 0.7015(2) 0.2715(2) 0.0242(11) Uani 1 1 d . . . C32 C 0.2158(7) 0.7252(2) 0.3408(2) 0.0258(11) Uani 1 1 d . . . H32 H 0.2485 0.6926 0.3715 0.031 Uiso 1 1 calc R . . C33 C 0.0204(7) 0.7471(3) 0.3556(2) 0.0284(12) Uani 1 1 d . . . H33A H -0.0063 0.7814 0.3273 0.034 Uiso 1 1 calc R . . H33B H -0.0667 0.7154 0.3441 0.034 Uiso 1 1 calc R . . C34 C -0.0131(8) 0.7654(3) 0.4265(3) 0.0335(13) Uani 1 1 d . . . H34 H 0.0959 0.7876 0.4424 0.040 Uiso 1 1 calc R . . C35 C -0.1815(8) 0.8049(2) 0.4337(3) 0.0333(12) Uani 1 1 d . . . H35A H -0.2850 0.7861 0.4107 0.040 Uiso 1 1 calc R . . H35B H -0.2138 0.8073 0.4802 0.040 Uiso 1 1 calc R . . C36 C -0.1566(10) 0.8672(3) 0.4075(3) 0.0470(16) Uani 1 1 d . . . H36A H -0.0651 0.8880 0.4337 0.071 Uiso 1 1 calc R . . H36B H -0.2728 0.8884 0.4098 0.071 Uiso 1 1 calc R . . H36C H -0.1158 0.8653 0.3624 0.071 Uiso 1 1 calc R . . C37 C 0.3552(9) 0.7747(3) 0.3466(3) 0.0437(16) Uani 1 1 d . . . H37A H 0.4719 0.7615 0.3287 0.066 Uiso 1 1 calc R . . H37B H 0.3713 0.7852 0.3923 0.066 Uiso 1 1 calc R . . H37C H 0.3121 0.8093 0.3224 0.066 Uiso 1 1 calc R . . C38 C -0.0376(10) 0.7097(3) 0.4693(3) 0.0410(15) Uani 1 1 d . . . H38A H -0.0375 0.7212 0.5151 0.062 Uiso 1 1 calc R . . H38B H 0.0628 0.6822 0.4612 0.062 Uiso 1 1 calc R . . H38C H -0.1536 0.6906 0.4585 0.062 Uiso 1 1 calc R . . N3 N 0.8836(7) 0.5449(2) 0.4586(2) 0.0284(10) Uani 1 1 d D . . H3N H 0.9244 0.5712 0.4308 0.034 Uiso 1 1 calc RD . . O9 O 0.8629(7) 0.5792(2) 0.83600(18) 0.0468(12) Uani 1 1 d . . . H9 H 0.7745 0.5634 0.8552 0.070 Uiso 1 1 calc R . . O10 O 0.6688(6) 0.43373(18) 0.59241(18) 0.0328(9) Uani 1 1 d . . . H10 H 0.6396 0.4015 0.5752 0.049 Uiso 1 1 calc R . . O11 O 0.8274(6) 0.48392(17) 0.37476(17) 0.0368(10) Uani 1 1 d . . . O12 O 0.5910(6) 0.36378(19) 0.50627(19) 0.0418(10) Uani 1 1 d . A . C39 C 0.8550(8) 0.5656(3) 0.7704(3) 0.0353(14) Uani 1 1 d . . . C40 C 0.8053(8) 0.6080(3) 0.7264(3) 0.0343(13) Uani 1 1 d . . . H40 H 0.7777 0.6468 0.7408 0.041 Uiso 1 1 calc R . . C41 C 0.7950(8) 0.5944(3) 0.6604(3) 0.0305(12) Uani 1 1 d . . . H41 H 0.7621 0.6241 0.6300 0.037 Uiso 1 1 calc R . . C42 C 0.8329(7) 0.5375(3) 0.6389(2) 0.0261(11) Uani 1 1 d . . . C43 C 0.8909(8) 0.4950(3) 0.6840(2) 0.0323(13) Uani 1 1 d . . . H43 H 0.9232 0.4565 0.6699 0.039 Uiso 1 1 calc R . . C44 C 0.9007(9) 0.5095(3) 0.7490(3) 0.0373(15) Uani 1 1 d . . . H44 H 0.9393 0.4806 0.7794 0.045 Uiso 1 1 calc R . . C45 C 0.8888(7) 0.5590(2) 0.5230(2) 0.0242(11) Uani 1 1 d . . . H45 H 0.9410 0.5955 0.5358 0.029 Uiso 1 1 calc R . . C46 C 0.8222(8) 0.5225(2) 0.5691(2) 0.0270(11) Uani 1 1 d . . . C47 C 0.7415(7) 0.4687(3) 0.5482(2) 0.0259(11) Uani 1 1 d . . . C48 C 0.7432(8) 0.4527(3) 0.4816(3) 0.0297(12) Uani 1 1 d . A . C49 C 0.8184(7) 0.4922(2) 0.4346(2) 0.0252(11) Uani 1 1 d . . . C50 C 0.6678(9) 0.3946(3) 0.4642(3) 0.0369(14) Uani 1 1 d D . . C51A C 0.7235(17) 0.3676(5) 0.3978(4) 0.050(2) Uani 0.708(9) 1 d PDU A 1 H51A H 0.7126 0.3988 0.3637 0.060 Uiso 0.708(9) 1 calc PR A 1 C52A C 0.5966(19) 0.3176(5) 0.3806(6) 0.060(3) Uani 0.708(9) 1 d PDU A 1 H52A H 0.6453 0.2976 0.3417 0.071 Uiso 0.708(9) 1 calc PR A 1 H52B H 0.5993 0.2886 0.4166 0.071 Uiso 0.708(9) 1 calc PR A 1 C53A C 0.4080(19) 0.3329(5) 0.3680(7) 0.075(3) Uani 0.708(9) 1 d PDU A 1 H53A H 0.3597 0.3569 0.4049 0.089 Uiso 0.708(9) 1 calc PR A 1 C54A C 0.389(2) 0.3690(6) 0.3032(8) 0.089(4) Uani 0.708(9) 1 d PDU A 1 H54A H 0.4922 0.3970 0.3015 0.107 Uiso 0.708(9) 1 calc PR A 1 H54B H 0.4057 0.3409 0.2669 0.107 Uiso 0.708(9) 1 calc PR A 1 C55A C 0.213(3) 0.4046(11) 0.2891(11) 0.115(7) Uani 0.708(9) 1 d PDU A 1 H55A H 0.1210 0.3783 0.2701 0.173 Uiso 0.708(9) 1 calc PR A 1 H55B H 0.2405 0.4365 0.2585 0.173 Uiso 0.708(9) 1 calc PR A 1 H55C H 0.1665 0.4214 0.3296 0.173 Uiso 0.708(9) 1 calc PR A 1 C56A C 0.9188(17) 0.3477(6) 0.4010(6) 0.066(3) Uani 0.708(9) 1 d PDU A 1 H56A H 0.9329 0.3186 0.4358 0.099 Uiso 0.708(9) 1 calc PR A 1 H56B H 0.9973 0.3818 0.4098 0.099 Uiso 0.708(9) 1 calc PR A 1 H56C H 0.9534 0.3298 0.3596 0.099 Uiso 0.708(9) 1 calc PR A 1 C57A C 0.294(2) 0.2758(6) 0.3610(9) 0.113(6) Uani 0.708(9) 1 d PDU A 1 H57A H 0.2079 0.2802 0.3249 0.170 Uiso 0.708(9) 1 calc PR A 1 H57B H 0.2261 0.2687 0.4012 0.170 Uiso 0.708(9) 1 calc PR A 1 H57C H 0.3750 0.2423 0.3526 0.170 Uiso 0.708(9) 1 calc PR A 1 C51B C 0.625(3) 0.3685(8) 0.3976(8) 0.036(4) Uani 0.292(9) 1 d PDU A 2 H51B H 0.7264 0.3792 0.3677 0.044 Uiso 0.292(9) 1 calc PR A 2 C52B C 0.454(3) 0.3904(11) 0.3692(10) 0.055(4) Uani 0.292(9) 1 d PDU A 2 H52C H 0.3522 0.3669 0.3870 0.065 Uiso 0.292(9) 1 calc PR A 2 H52D H 0.4366 0.4317 0.3833 0.065 Uiso 0.292(9) 1 calc PR A 2 C53B C 0.444(4) 0.3883(13) 0.2984(12) 0.069(5) Uani 0.292(9) 1 d PDU A 2 H53B H 0.5257 0.4205 0.2821 0.083 Uiso 0.292(9) 1 calc PR A 2 C54B C 0.499(5) 0.3317(12) 0.2613(13) 0.083(6) Uani 0.292(9) 1 d PDU A 2 H54C H 0.4663 0.3381 0.2153 0.099 Uiso 0.292(9) 1 calc PR A 2 H54D H 0.6336 0.3290 0.2633 0.099 Uiso 0.292(9) 1 calc PR A 2 C55B C 0.424(6) 0.2700(14) 0.280(2) 0.110(9) Uani 0.292(9) 1 d PDU A 2 H55D H 0.3407 0.2740 0.3171 0.164 Uiso 0.292(9) 1 calc PR A 2 H55E H 0.5256 0.2441 0.2925 0.164 Uiso 0.292(9) 1 calc PR A 2 H55F H 0.3587 0.2529 0.2434 0.164 Uiso 0.292(9) 1 calc PR A 2 C56B C 0.631(5) 0.3029(9) 0.4080(14) 0.061(6) Uani 0.292(9) 1 d PDU A 2 H56D H 0.5215 0.2848 0.3893 0.091 Uiso 0.292(9) 1 calc PR A 2 H56E H 0.6359 0.2945 0.4546 0.091 Uiso 0.292(9) 1 calc PR A 2 H56F H 0.7394 0.2867 0.3869 0.091 Uiso 0.292(9) 1 calc PR A 2 C57B C 0.251(4) 0.404(2) 0.2758(18) 0.064(7) Uani 0.292(9) 1 d PDU A 2 H57D H 0.1728 0.3690 0.2794 0.096 Uiso 0.292(9) 1 calc PR A 2 H57E H 0.2546 0.4170 0.2305 0.096 Uiso 0.292(9) 1 calc PR A 2 H57F H 0.2024 0.4356 0.3030 0.096 Uiso 0.292(9) 1 calc PR A 2 N4 N 0.3627(6) 0.5898(2) 0.7947(2) 0.0279(10) Uani 1 1 d D . . H4N H 0.4063 0.5643 0.8229 0.033 Uiso 1 1 calc RD . . O13 O 0.3758(6) 0.54566(19) 0.41920(16) 0.0348(9) Uani 1 1 d . . . H13A H 0.2995 0.5645 0.3970 0.052 Uiso 1 1 calc R . . O14 O 0.1315(6) 0.69513(18) 0.65980(19) 0.0366(9) Uani 1 1 d . . . H14 H 0.0868 0.7256 0.6767 0.055 Uiso 1 1 calc R . . O15 O 0.2899(6) 0.6491(2) 0.87882(18) 0.0393(9) Uani 1 1 d . . . O16 O 0.0394(8) 0.7652(2) 0.7446(2) 0.0618(15) Uani 1 1 d . B . C58 C 0.3604(7) 0.5622(3) 0.4846(2) 0.0276(12) Uani 1 1 d . . . C59 C 0.3242(8) 0.5191(2) 0.5301(2) 0.0263(11) Uani 1 1 d . . . H59 H 0.3119 0.4790 0.5175 0.032 Uiso 1 1 calc R . . C60 C 0.3059(7) 0.5354(2) 0.5948(2) 0.0260(11) Uani 1 1 d . . . H60 H 0.2813 0.5059 0.6263 0.031 Uiso 1 1 calc R . . C61 C 0.3229(7) 0.5941(2) 0.6146(2) 0.0243(10) Uani 1 1 d . . . C62 C 0.3660(8) 0.6365(2) 0.5669(2) 0.0283(12) Uani 1 1 d . . . H62 H 0.3814 0.6767 0.5790 0.034 Uiso 1 1 calc R . . C63 C 0.3859(8) 0.6200(3) 0.5026(3) 0.0304(12) Uani 1 1 d . . . H63 H 0.4173 0.6487 0.4709 0.036 Uiso 1 1 calc R . . C64 C 0.3762(8) 0.5760(2) 0.7307(2) 0.0280(12) Uani 1 1 d . . . H64 H 0.4384 0.5409 0.7184 0.034 Uiso 1 1 calc R . . C65 C 0.3038(7) 0.6106(2) 0.6841(2) 0.0227(10) Uani 1 1 d . . . C66 C 0.2113(7) 0.6630(2) 0.7051(3) 0.0273(11) Uani 1 1 d . . . C67 C 0.2054(8) 0.6798(2) 0.7706(2) 0.0277(12) Uani 1 1 d . B . C68 C 0.2848(8) 0.6415(3) 0.8191(3) 0.0301(12) Uani 1 1 d . . . C69 C 0.1164(10) 0.7361(3) 0.7879(3) 0.0438(15) Uani 1 1 d D . . C70A C 0.098(2) 0.7625(7) 0.8544(5) 0.047(3) Uani 0.566(8) 1 d PDU B 1 H70A H 0.2030 0.7513 0.8830 0.056 Uiso 0.566(8) 1 calc PR B 1 C71A C -0.083(2) 0.7346(6) 0.8780(6) 0.056(3) Uani 0.566(8) 1 d PDU B 1 H71A H -0.1820 0.7465 0.8482 0.067 Uiso 0.566(8) 1 calc PR B 1 H71B H -0.0718 0.6911 0.8760 0.067 Uiso 0.566(8) 1 calc PR B 1 C72A C -0.133(2) 0.7526(6) 0.9464(7) 0.066(3) Uani 0.566(8) 1 d PDU B 1 H72A H -0.1665 0.7954 0.9466 0.079 Uiso 0.566(8) 1 calc PR B 1 C73A C -0.302(3) 0.7153(7) 0.9676(10) 0.083(4) Uani 0.566(8) 1 d PDU B 1 H73A H -0.3451 0.6931 0.9293 0.099 Uiso 0.566(8) 1 calc PR B 1 H73B H -0.2598 0.6860 0.9999 0.099 Uiso 0.566(8) 1 calc PR B 1 C74A C -0.452(3) 0.7455(9) 0.9942(12) 0.106(6) Uani 0.566(8) 1 d PDU B 1 H74A H -0.4278 0.7545 1.0399 0.159 Uiso 0.566(8) 1 calc PR B 1 H74B H -0.5610 0.7206 0.9909 0.159 Uiso 0.566(8) 1 calc PR B 1 H74C H -0.4721 0.7823 0.9703 0.159 Uiso 0.566(8) 1 calc PR B 1 C75A C 0.076(2) 0.8308(5) 0.8502(6) 0.057(3) Uani 0.566(8) 1 d PDU B 1 H75A H 0.1876 0.8483 0.8330 0.085 Uiso 0.566(8) 1 calc PR B 1 H75B H 0.0517 0.8466 0.8936 0.085 Uiso 0.566(8) 1 calc PR B 1 H75C H -0.0267 0.8403 0.8214 0.085 Uiso 0.566(8) 1 calc PR B 1 C76A C 0.018(3) 0.7432(8) 0.9921(7) 0.093(5) Uani 0.566(8) 1 d PDU B 1 H76A H 0.0497 0.7012 0.9931 0.139 Uiso 0.566(8) 1 calc PR B 1 H76B H -0.0191 0.7560 1.0355 0.139 Uiso 0.566(8) 1 calc PR B 1 H76C H 0.1242 0.7662 0.9782 0.139 Uiso 0.566(8) 1 calc PR B 1 C70B C 0.138(4) 0.7588(14) 0.8562(11) 0.117(7) Uani 0.434(8) 1 d PDU B 2 H70B H 0.1447 0.7241 0.8860 0.140 Uiso 0.434(8) 1 calc PR B 2 C71B C -0.018(4) 0.8002(10) 0.8805(14) 0.117(6) Uani 0.434(8) 1 d PDU B 2 H71C H 0.0063 0.8084 0.9268 0.141 Uiso 0.434(8) 1 calc PR B 2 H71D H -0.0045 0.8381 0.8571 0.141 Uiso 0.434(8) 1 calc PR B 2 C72B C -0.216(4) 0.7829(9) 0.8753(13) 0.129(7) Uani 0.434(8) 1 d PDU B 2 H72B H -0.2489 0.7756 0.8289 0.155 Uiso 0.434(8) 1 calc PR B 2 C73B C -0.266(5) 0.7287(9) 0.9170(13) 0.130(7) Uani 0.434(8) 1 d PDU B 2 H73C H -0.3928 0.7174 0.9068 0.156 Uiso 0.434(8) 1 calc PR B 2 H73D H -0.1864 0.6954 0.9037 0.156 Uiso 0.434(8) 1 calc PR B 2 C74B C -0.250(6) 0.7357(10) 0.9858(13) 0.121(9) Uani 0.434(8) 1 d PDU B 2 H74D H -0.1210 0.7379 0.9979 0.181 Uiso 0.434(8) 1 calc PR B 2 H74E H -0.3065 0.7018 1.0075 0.181 Uiso 0.434(8) 1 calc PR B 2 H74F H -0.3120 0.7720 0.9990 0.181 Uiso 0.434(8) 1 calc PR B 2 C75B C 0.325(4) 0.7915(11) 0.8591(13) 0.129(8) Uani 0.434(8) 1 d PDU B 2 H75D H 0.4233 0.7634 0.8506 0.194 Uiso 0.434(8) 1 calc PR B 2 H75E H 0.3413 0.8089 0.9023 0.194 Uiso 0.434(8) 1 calc PR B 2 H75F H 0.3270 0.8228 0.8263 0.194 Uiso 0.434(8) 1 calc PR B 2 C76B C -0.331(5) 0.8321(10) 0.9026(15) 0.142(9) Uani 0.434(8) 1 d PDU B 2 H76D H -0.4204 0.8157 0.9328 0.214 Uiso 0.434(8) 1 calc PR B 2 H76E H -0.3939 0.8525 0.8672 0.214 Uiso 0.434(8) 1 calc PR B 2 H76F H -0.2523 0.8602 0.9257 0.214 Uiso 0.434(8) 1 calc PR B 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 N1 0.025(2) 0.041(3) 0.019(2) -0.0024(19) -0.0066(18) 0.001(2) O1 0.034(2) 0.052(2) 0.0202(17) -0.0106(17) 0.0009(16) 0.0000(19) O2 0.038(2) 0.039(2) 0.0197(17) 0.0026(16) -0.0019(17) 0.0036(18) O3 0.035(2) 0.048(2) 0.0174(18) 0.0005(17) 0.0028(16) 0.0026(19) O4 0.051(3) 0.036(2) 0.027(2) 0.0005(17) 0.0014(18) 0.0058(19) C1 0.016(2) 0.044(3) 0.017(2) -0.005(2) -0.0015(19) 0.002(2) C2 0.020(2) 0.041(3) 0.020(2) -0.006(2) -0.001(2) 0.003(2) C3 0.021(2) 0.035(3) 0.016(2) -0.006(2) 0.002(2) 0.002(2) C4 0.019(2) 0.033(3) 0.018(3) -0.001(2) -0.001(2) 0.001(2) C5 0.021(3) 0.039(3) 0.018(2) -0.001(2) 0.004(2) -0.006(2) C6 0.019(2) 0.043(3) 0.019(2) -0.007(2) -0.001(2) 0.000(2) C7 0.024(3) 0.040(3) 0.019(2) -0.002(2) 0.000(2) -0.002(2) C8 0.016(2) 0.035(3) 0.018(2) -0.004(2) 0.005(2) 0.000(2) C9 0.026(3) 0.038(3) 0.017(2) -0.005(2) 0.002(2) -0.004(2) C10 0.025(3) 0.035(3) 0.015(2) -0.003(2) 0.005(2) -0.003(2) C11 0.018(2) 0.042(3) 0.020(3) -0.003(2) -0.001(2) -0.006(2) C12 0.025(3) 0.042(3) 0.020(2) -0.009(2) 0.005(2) -0.006(2) C13 0.020(2) 0.044(3) 0.020(2) -0.007(2) 0.002(2) 0.000(2) C14 0.025(3) 0.038(3) 0.030(3) -0.006(2) 0.000(2) 0.004(2) C15 0.028(3) 0.046(3) 0.028(3) -0.010(3) -0.001(2) -0.005(3) C16 0.028(3) 0.042(3) 0.045(3) -0.008(3) -0.009(3) 0.002(3) C17 0.050(4) 0.043(4) 0.076(5) -0.007(4) -0.003(4) -0.002(3) C18 0.032(3) 0.059(4) 0.037(3) -0.017(3) 0.005(3) 0.012(3) C19 0.054(4) 0.067(5) 0.037(4) 0.002(3) 0.000(3) -0.017(4) N2 0.020(2) 0.034(2) 0.018(2) -0.0030(18) -0.0045(17) 0.0004(19) O5 0.047(3) 0.071(3) 0.0189(18) -0.018(2) -0.0004(19) 0.002(2) O6 0.0288(19) 0.034(2) 0.0192(16) 0.0024(15) 0.0031(15) -0.0024(17) O7 0.034(2) 0.037(2) 0.0237(18) 0.0019(16) 0.0006(16) -0.0007(17) O8 0.0286(19) 0.041(2) 0.0164(18) -0.0021(16) -0.0031(15) 0.0043(17) C20 0.024(3) 0.055(4) 0.018(3) -0.013(3) 0.001(2) -0.005(3) C21 0.027(3) 0.046(3) 0.027(3) -0.011(2) 0.000(2) 0.001(3) C22 0.020(3) 0.039(3) 0.024(3) -0.003(2) -0.001(2) -0.003(2) C23 0.021(2) 0.040(3) 0.016(2) -0.005(2) 0.0015(19) -0.003(2) C24 0.024(3) 0.044(3) 0.016(2) -0.006(2) 0.001(2) -0.004(2) C25 0.026(3) 0.054(4) 0.017(3) -0.002(2) 0.000(2) -0.003(3) C26 0.020(2) 0.040(3) 0.010(2) -0.004(2) 0.0040(19) 0.003(2) C27 0.013(2) 0.033(3) 0.018(2) -0.004(2) -0.0010(19) 0.001(2) C28 0.021(3) 0.036(3) 0.016(2) -0.003(2) -0.001(2) 0.003(2) C29 0.024(3) 0.029(3) 0.016(2) 0.003(2) 0.000(2) -0.001(2) C30 0.023(3) 0.032(3) 0.018(2) -0.003(2) 0.001(2) 0.006(2) C31 0.016(3) 0.039(3) 0.018(2) -0.004(2) -0.001(2) 0.003(2) C32 0.020(3) 0.039(3) 0.018(2) -0.004(2) -0.002(2) 0.003(2) C33 0.024(3) 0.039(3) 0.022(2) -0.007(2) 0.000(2) 0.004(2) C34 0.028(3) 0.039(3) 0.034(3) -0.007(3) -0.001(2) 0.003(2) C35 0.025(3) 0.038(3) 0.037(3) -0.006(2) 0.001(2) 0.002(2) C36 0.049(4) 0.042(3) 0.050(4) -0.007(3) 0.006(3) 0.011(3) C37 0.031(3) 0.058(4) 0.041(3) -0.017(3) 0.000(3) -0.017(3) C38 0.050(4) 0.048(4) 0.025(3) -0.004(3) 0.007(3) 0.010(3) N3 0.033(2) 0.035(2) 0.018(2) 0.0043(19) 0.0019(18) -0.002(2) O9 0.046(3) 0.078(3) 0.0170(18) -0.005(2) -0.0021(18) -0.018(2) O10 0.030(2) 0.042(2) 0.0257(19) 0.0097(17) 0.0018(17) -0.0045(18) O11 0.055(3) 0.040(2) 0.0161(18) 0.0004(16) 0.0007(17) -0.003(2) O12 0.054(3) 0.039(2) 0.033(2) 0.0065(19) -0.003(2) -0.012(2) C39 0.029(3) 0.062(4) 0.015(2) 0.003(3) 0.003(2) -0.012(3) C40 0.024(3) 0.054(4) 0.025(3) -0.006(3) 0.001(2) -0.004(3) C41 0.030(3) 0.047(3) 0.015(2) 0.004(2) 0.002(2) -0.007(3) C42 0.020(3) 0.044(3) 0.014(2) 0.006(2) -0.001(2) -0.006(2) C43 0.032(3) 0.041(3) 0.024(3) 0.008(2) 0.000(2) -0.004(3) C44 0.040(3) 0.058(4) 0.014(2) 0.005(3) -0.006(2) -0.019(3) C45 0.023(3) 0.034(3) 0.016(2) 0.003(2) 0.006(2) -0.002(2) C46 0.025(3) 0.035(3) 0.021(3) 0.004(2) 0.001(2) -0.002(2) C47 0.019(3) 0.037(3) 0.021(2) 0.010(2) -0.001(2) -0.004(2) C48 0.027(3) 0.040(3) 0.021(3) 0.008(2) 0.003(2) 0.001(2) C49 0.022(3) 0.035(3) 0.020(3) 0.001(2) -0.003(2) 0.005(2) C50 0.042(3) 0.040(3) 0.029(3) -0.003(3) -0.007(3) 0.003(3) C51A 0.077(6) 0.047(5) 0.027(4) 0.014(4) -0.021(5) -0.022(5) C52A 0.093(6) 0.045(5) 0.040(5) 0.004(4) -0.025(5) -0.022(5) C53A 0.093(6) 0.040(5) 0.090(6) 0.015(4) -0.034(6) -0.022(5) C54A 0.113(9) 0.047(6) 0.106(8) 0.017(6) -0.055(7) -0.017(6) C55A 0.148(15) 0.092(11) 0.105(14) 0.023(11) -0.077(12) -0.006(12) C56A 0.075(6) 0.063(7) 0.060(6) -0.013(5) 0.022(6) 0.000(6) C57A 0.122(11) 0.079(8) 0.138(12) 0.030(8) -0.071(10) -0.059(8) C51B 0.046(9) 0.036(9) 0.028(8) -0.018(7) 0.010(7) -0.018(8) C52B 0.049(9) 0.059(9) 0.055(9) 0.002(8) -0.002(7) -0.022(8) C53B 0.055(9) 0.087(10) 0.065(9) 0.000(9) -0.008(8) -0.017(9) C54B 0.073(12) 0.097(12) 0.079(11) -0.013(10) -0.004(10) -0.015(10) C55B 0.10(2) 0.102(13) 0.12(2) -0.021(16) 0.020(18) -0.028(16) C56B 0.091(16) 0.040(10) 0.051(14) -0.020(10) 0.025(13) -0.002(11) C57B 0.033(10) 0.104(17) 0.055(13) 0.002(14) 0.005(9) -0.038(10) N4 0.024(2) 0.038(2) 0.021(2) -0.0010(19) -0.0041(18) 0.003(2) O13 0.033(2) 0.058(2) 0.0128(16) 0.0003(17) 0.0010(15) 0.0109(19) O14 0.042(2) 0.040(2) 0.0271(19) 0.0040(17) -0.0017(18) 0.004(2) O15 0.038(2) 0.059(2) 0.0215(18) -0.0067(19) 0.0012(16) -0.006(2) O16 0.082(4) 0.052(3) 0.051(3) -0.009(2) -0.005(3) 0.025(3) C58 0.020(3) 0.052(3) 0.011(2) 0.001(2) -0.001(2) 0.006(2) C59 0.024(3) 0.032(3) 0.022(3) -0.003(2) -0.003(2) 0.002(2) C60 0.026(3) 0.036(3) 0.016(2) 0.004(2) -0.003(2) -0.003(2) C61 0.019(2) 0.035(3) 0.019(2) 0.004(2) 0.002(2) 0.002(2) C62 0.029(3) 0.036(3) 0.020(2) 0.005(2) 0.001(2) 0.002(2) C63 0.031(3) 0.039(3) 0.021(3) 0.007(2) 0.005(2) 0.003(2) C64 0.028(3) 0.034(3) 0.021(3) 0.001(2) -0.002(2) -0.003(2) C65 0.022(2) 0.028(2) 0.018(2) 0.000(2) -0.001(2) -0.001(2) C66 0.022(3) 0.035(3) 0.025(3) -0.001(2) -0.002(2) -0.004(2) C67 0.027(3) 0.036(3) 0.021(3) -0.003(2) 0.000(2) 0.002(2) C68 0.026(3) 0.043(3) 0.021(3) -0.005(2) 0.000(2) -0.001(2) C69 0.044(4) 0.047(4) 0.040(3) -0.006(3) 0.005(3) 0.011(3) C70A 0.073(7) 0.032(6) 0.035(6) 0.000(5) 0.015(5) 0.010(5) C71A 0.075(7) 0.043(5) 0.050(5) 0.005(5) 0.024(5) -0.001(5) C72A 0.109(8) 0.032(5) 0.057(6) 0.000(5) 0.046(5) -0.005(6) C73A 0.110(9) 0.050(7) 0.089(9) 0.008(7) 0.061(7) 0.001(6) C74A 0.071(10) 0.079(10) 0.168(16) -0.039(11) 0.015(10) -0.003(8) C75A 0.097(10) 0.026(5) 0.047(6) -0.009(5) -0.002(7) -0.003(6) C76A 0.172(12) 0.064(8) 0.042(6) -0.015(7) 0.016(7) -0.042(10) C70B 0.197(16) 0.061(11) 0.092(12) -0.044(10) -0.002(13) 0.051(11) C71B 0.198(16) 0.056(9) 0.099(11) -0.036(8) 0.012(12) 0.051(10) C72B 0.201(16) 0.067(8) 0.119(11) -0.012(8) 0.032(13) 0.043(10) C73B 0.204(17) 0.070(9) 0.116(12) -0.006(9) 0.020(14) 0.049(11) C74B 0.20(2) 0.044(11) 0.114(13) -0.030(10) -0.024(18) -0.004(14) C75B 0.173(16) 0.092(13) 0.123(16) -0.085(12) -0.070(15) 0.064(12) C76B 0.206(19) 0.064(11) 0.157(19) 0.007(13) 0.076(18) 0.042(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 N1 C7 1.367(7) . ? N1 C11 1.377(7) . ? O1 C1 1.363(6) . ? O2 C9 1.317(7) . ? O3 C11 1.273(6) . ? O4 C12 1.256(7) . ? C1 C6 1.375(8) . ? C1 C2 1.412(8) . ? C2 C3 1.389(7) . ? C3 C4 1.406(8) . ? C4 C5 1.401(7) . ? C4 C8 1.489(7) . ? C5 C6 1.389(7) . ? C7 C8 1.357(8) . ? C8 C9 1.425(8) . ? C9 C10 1.437(7) . ? C10 C11 1.407(8) . ? C10 C12 1.475(8) . ? C12 C13 1.504(7) . ? C13 C18 1.528(8) . ? C13 C14 1.546(8) . ? C14 C15 1.530(7) . ? C15 C19 1.525(9) . ? C15 C16 1.536(8) . ? C16 C17 1.533(10) . ? N2 C26 1.353(6) . ? N2 C30 1.366(7) . ? O5 C20 1.378(6) . ? O6 C28 1.343(6) . ? O7 C31 1.249(6) . ? O8 C30 1.268(6) . ? C20 C25 1.382(9) . ? C20 C21 1.386(9) . ? C21 C22 1.401(7) . ? C22 C23 1.391(8) . ? C23 C24 1.380(8) . ? C23 C27 1.485(7) . ? C24 C25 1.405(7) . ? C26 C27 1.383(8) . ? C27 C28 1.409(8) . ? C28 C29 1.411(7) . ? C29 C30 1.443(7) . ? C29 C31 1.469(8) . ? C31 C32 1.526(7) . ? C32 C37 1.523(8) . ? C32 C33 1.548(7) . ? C33 C34 1.540(7) . ? C34 C35 1.533(8) . ? C34 C38 1.548(9) . ? C35 C36 1.521(9) . ? N3 C45 1.365(6) . ? N3 C49 1.378(7) . ? O9 C39 1.388(7) . ? O10 C47 1.320(6) . ? O11 C49 1.251(6) . ? O12 C50 1.249(7) . ? C39 C40 1.370(9) . ? C39 C44 1.386(9) . ? C40 C41 1.397(7) . ? C41 C42 1.391(8) . ? C42 C43 1.403(8) . ? C42 C46 1.480(7) . ? C43 C44 1.381(8) . ? C45 C46 1.351(7) . ? C46 C47 1.422(8) . ? C47 C48 1.422(7) . ? C48 C49 1.430(8) . ? C48 C50 1.471(8) . ? C50 C51B 1.526(15) . ? C50 C51A 1.555(11) . ? C51A C56A 1.503(16) . ? C51A C52A 1.507(15) . ? C52A C53A 1.449(18) . ? C53A C57A 1.547(16) . ? C53A C54A 1.573(18) . ? C54A C55A 1.55(2) . ? C51B C52B 1.47(2) . ? C51B C56B 1.50(2) . ? C52B C53B 1.46(2) . ? C53B C54B 1.55(3) . ? C53B C57B 1.53(2) . ? C54B C55B 1.55(3) . ? N4 C64 1.361(7) . ? N4 C68 1.396(7) . ? O13 C58 1.404(6) . ? O14 C66 1.319(7) . ? O15 C68 1.244(7) . ? O16 C69 1.244(8) . ? C58 C63 1.374(8) . ? C58 C59 1.381(8) . ? C59 C60 1.390(7) . ? C60 C61 1.396(8) . ? C61 C62 1.410(7) . ? C61 C65 1.488(7) . ? C62 C63 1.387(7) . ? C64 C65 1.349(7) . ? C65 C66 1.435(8) . ? C66 C67 1.404(7) . ? C67 C68 1.445(8) . ? C67 C69 1.478(8) . ? C69 C70A 1.501(12) . ? C69 C70B 1.508(18) . ? C70A C71A 1.550(19) . ? C70A C75A 1.557(17) . ? C71A C72A 1.515(17) . ? C72A C76A 1.47(2) . ? C72A C73A 1.56(2) . ? C73A C74A 1.41(2) . ? C70B C75B 1.56(2) . ? C70B C71B 1.56(2) . ? C71B C72B 1.50(2) . ? C72B C76B 1.51(2) . ? C72B C73B 1.54(3) . ? C73B C74B 1.43(3) . ? 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 C7 N1 C11 123.4(5) . . ? O1 C1 C6 123.3(5) . . ? O1 C1 C2 116.9(5) . . ? C6 C1 C2 119.8(5) . . ? C3 C2 C1 119.2(5) . . ? C2 C3 C4 121.5(5) . . ? C5 C4 C3 117.9(5) . . ? C5 C4 C8 123.2(5) . . ? C3 C4 C8 118.9(5) . . ? C6 C5 C4 120.9(5) . . ? C1 C6 C5 120.8(5) . . ? C8 C7 N1 121.6(5) . . ? C7 C8 C9 117.5(5) . . ? C7 C8 C4 120.7(5) . . ? C9 C8 C4 121.7(5) . . ? O2 C9 C8 118.3(4) . . ? O2 C9 C10 121.0(5) . . ? C8 C9 C10 120.7(5) . . ? C11 C10 C9 118.5(5) . . ? C11 C10 C12 123.5(4) . . ? C9 C10 C12 118.0(5) . . ? O3 C11 N1 116.4(5) . . ? O3 C11 C10 126.1(5) . . ? N1 C11 C10 117.5(4) . . ? O4 C12 C10 119.2(5) . . ? O4 C12 C13 117.2(5) . . ? C10 C12 C13 123.5(5) . . ? C12 C13 C18 110.2(5) . . ? C12 C13 C14 107.6(4) . . ? C18 C13 C14 112.6(5) . . ? C15 C14 C13 114.1(5) . . ? C14 C15 C19 112.0(5) . . ? C14 C15 C16 111.5(5) . . ? C19 C15 C16 108.5(5) . . ? C17 C16 C15 114.2(5) . . ? C26 N2 C30 125.0(5) . . ? O5 C20 C25 121.5(6) . . ? O5 C20 C21 117.3(5) . . ? C25 C20 C21 121.2(5) . . ? C20 C21 C22 118.8(6) . . ? C23 C22 C21 121.2(5) . . ? C24 C23 C22 118.5(5) . . ? C24 C23 C27 121.0(5) . . ? C22 C23 C27 120.4(5) . . ? C23 C24 C25 121.5(6) . . ? C20 C25 C24 118.7(6) . . ? N2 C26 C27 120.9(5) . . ? C26 C27 C28 116.6(5) . . ? C26 C27 C23 119.9(5) . . ? C28 C27 C23 123.4(5) . . ? O6 C28 C27 117.4(4) . . ? O6 C28 C29 119.9(5) . . ? C27 C28 C29 122.7(5) . . ? C28 C29 C30 117.8(5) . . ? C28 C29 C31 118.6(4) . . ? C30 C29 C31 123.6(4) . . ? O8 C30 N2 117.5(5) . . ? O8 C30 C29 126.0(5) . . ? N2 C30 C29 116.5(4) . . ? O7 C31 C29 119.9(4) . . ? O7 C31 C32 117.7(5) . . ? C29 C31 C32 122.3(4) . . ? C37 C32 C31 109.8(4) . . ? C37 C32 C33 111.8(5) . . ? C31 C32 C33 106.8(4) . . ? C34 C33 C32 115.0(4) . . ? C35 C34 C33 112.2(5) . . ? C35 C34 C38 109.0(5) . . ? C33 C34 C38 109.9(5) . . ? C36 C35 C34 114.2(5) . . ? C45 N3 C49 124.0(4) . . ? C40 C39 C44 119.7(5) . . ? C40 C39 O9 120.0(6) . . ? C44 C39 O9 120.3(6) . . ? C39 C40 C41 120.3(6) . . ? C42 C41 C40 120.2(5) . . ? C41 C42 C43 119.0(5) . . ? C41 C42 C46 120.7(5) . . ? C43 C42 C46 120.2(5) . . ? C44 C43 C42 119.7(6) . . ? C43 C44 C39 121.0(6) . . ? C46 C45 N3 122.2(5) . . ? C45 C46 C47 117.5(5) . . ? C45 C46 C42 121.8(5) . . ? C47 C46 C42 120.8(5) . . ? O10 C47 C46 118.3(5) . . ? O10 C47 C48 121.2(5) . . ? C46 C47 C48 120.5(5) . . ? C47 C48 C49 119.9(5) . . ? C47 C48 C50 117.4(5) . . ? C49 C48 C50 122.7(5) . . ? O11 C49 N3 117.8(5) . . ? O11 C49 C48 126.5(5) . . ? N3 C49 C48 115.7(5) . . ? O12 C50 C48 120.0(5) . . ? O12 C50 C51B 108.4(9) . . ? C48 C50 C51B 130.0(9) . . ? O12 C50 C51A 120.8(6) . . ? C48 C50 C51A 117.8(6) . . ? C51B C50 C51A 27.2(8) . . ? C56A C51A C52A 112.0(10) . . ? C56A C51A C50 109.3(8) . . ? C52A C51A C50 109.8(9) . . ? C53A C52A C51A 116.9(10) . . ? C52A C53A C57A 109.5(11) . . ? C52A C53A C54A 111.1(12) . . ? C57A C53A C54A 107.9(10) . . ? C55A C54A C53A 120.2(16) . . ? C52B C51B C56B 115(2) . . ? C52B C51B C50 113.8(16) . . ? C56B C51B C50 104.4(16) . . ? C53B C52B C51B 115.4(18) . . ? C52B C53B C54B 120(2) . . ? C52B C53B C57B 110(2) . . ? C54B C53B C57B 106(2) . . ? C55B C54B C53B 122(2) . . ? C64 N4 C68 125.0(5) . . ? C63 C58 C59 121.1(5) . . ? C63 C58 O13 120.2(5) . . ? C59 C58 O13 118.7(5) . . ? C58 C59 C60 119.0(5) . . ? C59 C60 C61 121.6(5) . . ? C60 C61 C62 117.7(5) . . ? C60 C61 C65 120.8(4) . . ? C62 C61 C65 121.5(5) . . ? C63 C62 C61 120.5(5) . . ? C58 C63 C62 120.0(5) . . ? C65 C64 N4 121.8(5) . . ? C64 C65 C66 116.9(5) . . ? C64 C65 C61 120.1(5) . . ? C66 C65 C61 122.9(4) . . ? O14 C66 C67 121.2(5) . . ? O14 C66 C65 116.9(5) . . ? C67 C66 C65 121.9(5) . . ? C66 C67 C68 119.4(5) . . ? C66 C67 C69 118.7(5) . . ? C68 C67 C69 121.9(5) . . ? O15 C68 N4 117.4(5) . . ? O15 C68 C67 127.9(5) . . ? N4 C68 C67 114.7(5) . . ? O16 C69 C67 118.9(6) . . ? O16 C69 C70A 113.8(8) . . ? C67 C69 C70A 127.2(8) . . ? O16 C69 C70B 122.5(14) . . ? C67 C69 C70B 118.3(13) . . ? C70A C69 C70B 11.7(13) . . ? C69 C70A C71A 101.6(10) . . ? C69 C70A C75A 110.8(10) . . ? C71A C70A C75A 109.3(11) . . ? C72A C71A C70A 113.1(11) . . ? C76A C72A C71A 112.1(13) . . ? C76A C72A C73A 109.8(13) . . ? C71A C72A C73A 108.0(13) . . ? C74A C73A C72A 118.0(14) . . ? C69 C70B C75B 106.8(17) . . ? C69 C70B C71B 115(2) . . ? C75B C70B C71B 110.4(19) . . ? C72B C71B C70B 121.9(18) . . ? C76B C72B C71B 109(2) . . ? C76B C72B C73B 104.3(18) . . ? C71B C72B C73B 113(2) . . ? C74B C73B C72B 116(2) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 66.19 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.277 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 941138' ####################################################################### # # 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_zw_ii_15_f3_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 N O3' _chemical_formula_sum 'C13 H19 N O3' _chemical_formula_weight 237.29 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _space_group_name_H-M_alt P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0939(16) _cell_length_b 30.695(5) _cell_length_c 9.1390(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.405(5) _cell_angle_gamma 90.00 _cell_volume 2543.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9983 _cell_measurement_theta_min 5.09 _cell_measurement_theta_max 66.20 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5946 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Microstar Pt 135 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60175 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.85 _diffrn_reflns_theta_max 66.81 _reflns_number_total 8598 _reflns_number_gt 8575 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker PROTEUM' _computing_cell_refinement 'Bruker PROTEUM' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0486P)^2^+0.4025P] 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 0.03(8) _refine_ls_number_reflns 8598 _refine_ls_number_parameters 642 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.59430(11) 0.45520(3) 0.15725(11) 0.0260(2) Uani 1 1 d . . . O2 O 0.90528(11) 0.46157(3) 0.60333(10) 0.0264(2) Uani 1 1 d . . . H2 H 0.8849 0.4883 0.5997 0.040 Uiso 1 1 calc R . . O3 O 0.79302(11) 0.53018(3) 0.50519(10) 0.0262(2) Uani 1 1 d . . . N1 N 0.69497(12) 0.39514(4) 0.26627(12) 0.0206(2) Uani 1 1 d D . . H1N H 0.6379(17) 0.3782(5) 0.2011(16) 0.025 Uiso 1 1 d D . . C1 C 0.67634(14) 0.43986(4) 0.26018(15) 0.0202(3) Uani 1 1 d . . . C2 C 0.78560(14) 0.37455(4) 0.36786(15) 0.0220(3) Uani 1 1 d . . . H2A H 0.7951 0.3438 0.3627 0.026 Uiso 1 1 calc R . . C3 C 0.86321(14) 0.39635(5) 0.47676(15) 0.0229(3) Uani 1 1 d . . . H3 H 0.9307 0.3817 0.5443 0.028 Uiso 1 1 calc R . . C4 C 0.84022(14) 0.44167(5) 0.48634(14) 0.0210(3) Uani 1 1 d . . . C5 C 0.75285(14) 0.46453(4) 0.37737(14) 0.0195(3) Uani 1 1 d . . . C6 C 0.73877(14) 0.51206(4) 0.39128(14) 0.0207(3) Uani 1 1 d . . . C7 C 0.67017(14) 0.54042(4) 0.26884(15) 0.0208(3) Uani 1 1 d . . . H7 H 0.5873 0.5242 0.2153 0.025 Uiso 1 1 calc R . . C8 C 0.79196(14) 0.54878(4) 0.16330(14) 0.0221(3) Uani 1 1 d . . . H8A H 0.8685 0.5674 0.2145 0.027 Uiso 1 1 calc R . . H8B H 0.8388 0.5205 0.1428 0.027 Uiso 1 1 calc R . . C9 C 0.74285(16) 0.57036(5) 0.01612(15) 0.0277(3) Uani 1 1 d . . . H9 H 0.6792 0.5960 0.0353 0.033 Uiso 1 1 calc R . . C10 C 0.87857(17) 0.58645(5) -0.05653(16) 0.0308(3) Uani 1 1 d . . . H10A H 0.9422 0.5611 -0.0737 0.037 Uiso 1 1 calc R . . H10B H 0.9351 0.6061 0.0128 0.037 Uiso 1 1 calc R . . C11 C 0.8467(2) 0.61048(5) -0.20193(17) 0.0381(4) Uani 1 1 d . . . H11A H 0.7765 0.6341 -0.1888 0.057 Uiso 1 1 calc R . . H11B H 0.8045 0.5901 -0.2763 0.057 Uiso 1 1 calc R . . H11C H 0.9386 0.6226 -0.2339 0.057 Uiso 1 1 calc R . . C12 C 0.61060(15) 0.58254(4) 0.33028(17) 0.0260(3) Uani 1 1 d . . . H12A H 0.6916 0.5988 0.3817 0.039 Uiso 1 1 calc R . . H12B H 0.5363 0.5756 0.3989 0.039 Uiso 1 1 calc R . . H12C H 0.5656 0.6003 0.2496 0.039 Uiso 1 1 calc R . . C13 C 0.6533(2) 0.53840(7) -0.08383(18) 0.0467(4) Uani 1 1 d . . . H13A H 0.7154 0.5135 -0.1057 0.070 Uiso 1 1 calc R . . H13B H 0.6194 0.5531 -0.1755 0.070 Uiso 1 1 calc R . . H13C H 0.5679 0.5282 -0.0343 0.070 Uiso 1 1 calc R . . O4 O 0.64903(11) 0.79848(3) 0.56521(10) 0.0247(2) Uani 1 1 d . . . O5 O 0.21875(10) 0.78955(3) 0.23177(11) 0.0264(2) Uani 1 1 d . . . H5 H 0.2225 0.7630 0.2534 0.040 Uiso 1 1 calc R . . O6 O 0.31223(11) 0.72204(3) 0.35443(11) 0.0270(2) Uani 1 1 d . . . N2 N 0.54393(13) 0.85791(4) 0.45596(12) 0.0198(2) Uani 1 1 d . . . H2N H 0.6071(19) 0.8728(5) 0.5130(19) 0.024 Uiso 1 1 d . . . C14 C 0.54957(15) 0.81330(4) 0.47768(14) 0.0188(3) Uani 1 1 d . . . C15 C 0.44653(15) 0.87786(4) 0.35908(14) 0.0205(3) Uani 1 1 d . . . H15 H 0.4524 0.9085 0.3472 0.025 Uiso 1 1 calc R . . C16 C 0.34101(15) 0.85550(4) 0.27846(14) 0.0222(3) Uani 1 1 d . . . H16 H 0.2757 0.8698 0.2077 0.027 Uiso 1 1 calc R . . C17 C 0.33116(14) 0.81028(5) 0.30296(14) 0.0203(3) Uani 1 1 d . . . C18 C 0.43542(14) 0.78812(4) 0.39784(14) 0.0190(3) Uani 1 1 d . . . C19 C 0.42176(14) 0.74061(4) 0.41535(14) 0.0195(3) Uani 1 1 d . . . C20 C 0.53994(14) 0.71304(4) 0.49631(14) 0.0195(3) Uani 1 1 d . . . H20 H 0.5799 0.7289 0.5864 0.023 Uiso 1 1 calc R . . C21 C 0.66436(14) 0.70731(4) 0.39112(13) 0.0200(3) Uani 1 1 d . . . H21A H 0.6268 0.6884 0.3087 0.024 Uiso 1 1 calc R . . H21B H 0.6860 0.7362 0.3495 0.024 Uiso 1 1 calc R . . C22 C 0.80963(15) 0.68778(4) 0.45868(14) 0.0217(3) Uani 1 1 d . . . H22 H 0.7852 0.6621 0.5196 0.026 Uiso 1 1 calc R . . C23 C 0.90299(15) 0.67173(5) 0.33694(15) 0.0248(3) Uani 1 1 d . . . H23A H 0.8395 0.6546 0.2655 0.030 Uiso 1 1 calc R . . H23B H 0.9396 0.6973 0.2845 0.030 Uiso 1 1 calc R . . C24 C 1.03441(16) 0.64378(5) 0.39243(18) 0.0336(3) Uani 1 1 d . . . H24A H 0.9995 0.6186 0.4457 0.050 Uiso 1 1 calc R . . H24B H 1.1014 0.6611 0.4583 0.050 Uiso 1 1 calc R . . H24C H 1.0867 0.6337 0.3089 0.050 Uiso 1 1 calc R . . C25 C 0.47565(15) 0.66943(4) 0.54086(15) 0.0226(3) Uani 1 1 d . . . H25A H 0.4401 0.6533 0.4527 0.034 Uiso 1 1 calc R . . H25B H 0.3935 0.6746 0.6020 0.034 Uiso 1 1 calc R . . H25C H 0.5522 0.6524 0.5964 0.034 Uiso 1 1 calc R . . C26 C 0.89498(16) 0.72065(5) 0.55885(17) 0.0302(3) Uani 1 1 d . . . H26A H 0.9259 0.7452 0.5001 0.045 Uiso 1 1 calc R . . H26B H 0.9822 0.7065 0.6074 0.045 Uiso 1 1 calc R . . H26C H 0.8314 0.7312 0.6331 0.045 Uiso 1 1 calc R . . O7 O 0.89402(11) 0.84178(3) 0.29053(11) 0.0271(2) Uani 1 1 d . . . H7A H 0.9003 0.8156 0.2654 0.041 Uiso 1 1 calc R . . O8 O 0.50054(10) 0.84667(3) -0.08650(10) 0.0243(2) Uani 1 1 d . . . O9 O 0.82526(11) 0.77388(3) 0.16028(10) 0.0246(2) Uani 1 1 d . . . N3 N 0.58712(12) 0.90707(3) 0.03117(12) 0.0194(2) Uani 1 1 d D . . H3N H 0.5220(16) 0.9224(5) -0.0318(16) 0.023 Uiso 1 1 d D . . C27 C 0.79140(14) 0.86145(4) 0.20393(14) 0.0197(3) Uani 1 1 d . . . C28 C 0.77869(15) 0.90704(4) 0.22089(14) 0.0216(3) Uani 1 1 d . . . H28 H 0.8400 0.9223 0.2925 0.026 Uiso 1 1 calc R . . C29 C 0.67668(15) 0.92832(4) 0.13215(14) 0.0206(3) Uani 1 1 d . . . H29 H 0.6678 0.9590 0.1411 0.025 Uiso 1 1 calc R . . C30 C 0.59060(14) 0.86243(4) 0.00833(14) 0.0185(3) Uani 1 1 d . . . C31 C 0.70017(14) 0.83846(4) 0.09820(14) 0.0187(3) Uani 1 1 d . . . C32 C 0.72723(14) 0.79175(4) 0.07864(14) 0.0195(3) Uani 1 1 d . . . C33 C 0.64533(15) 0.76392(4) -0.03866(14) 0.0204(3) Uani 1 1 d . . . H33 H 0.6313 0.7812 -0.1315 0.024 Uiso 1 1 calc R . . C34 C 0.49238(15) 0.75117(4) 0.01088(14) 0.0207(3) Uani 1 1 d . . . H34A H 0.5064 0.7313 0.0963 0.025 Uiso 1 1 calc R . . H34B H 0.4425 0.7777 0.0434 0.025 Uiso 1 1 calc R . . C35 C 0.39183(15) 0.72874(4) -0.10956(14) 0.0233(3) Uani 1 1 d . . . H35 H 0.4546 0.7083 -0.1631 0.028 Uiso 1 1 calc R . . C36 C 0.27038(19) 0.70181(5) -0.04720(17) 0.0365(4) Uani 1 1 d . . . H36A H 0.2186 0.7203 0.0213 0.044 Uiso 1 1 calc R . . H36B H 0.1978 0.6935 -0.1287 0.044 Uiso 1 1 calc R . . C37 C 0.3238(3) 0.66071(6) 0.0333(2) 0.0527(5) Uani 1 1 d . . . H37A H 0.3868 0.6687 0.1210 0.079 Uiso 1 1 calc R . . H37B H 0.3801 0.6429 -0.0315 0.079 Uiso 1 1 calc R . . H37C H 0.2387 0.6441 0.0623 0.079 Uiso 1 1 calc R . . C38 C 0.73591(17) 0.72331(4) -0.06699(16) 0.0271(3) Uani 1 1 d . . . H38A H 0.7411 0.7046 0.0202 0.041 Uiso 1 1 calc R . . H38B H 0.8358 0.7319 -0.0884 0.041 Uiso 1 1 calc R . . H38C H 0.6890 0.7073 -0.1509 0.041 Uiso 1 1 calc R . . C39 C 0.32630(16) 0.76191(5) -0.22087(15) 0.0262(3) Uani 1 1 d . . . H39A H 0.4060 0.7788 -0.2599 0.039 Uiso 1 1 calc R . . H39B H 0.2603 0.7816 -0.1727 0.039 Uiso 1 1 calc R . . H39C H 0.2706 0.7466 -0.3014 0.039 Uiso 1 1 calc R . . O10 O 0.27310(10) 0.40606(3) 0.34966(10) 0.0244(2) Uani 1 1 d . . . O11 O -0.10127(10) 0.41192(3) -0.04710(10) 0.0244(2) Uani 1 1 d . . . H11 H -0.0772 0.4383 -0.0511 0.037 Uiso 1 1 calc R . . O12 O 0.03382(10) 0.47951(3) 0.02077(10) 0.0225(2) Uani 1 1 d . . . N4 N 0.15070(12) 0.34621(4) 0.26426(12) 0.0202(2) Uani 1 1 d D . . H4N H 0.2155(16) 0.3303(5) 0.3248(16) 0.024 Uiso 1 1 d D . . C40 C 0.17715(14) 0.39064(4) 0.26016(14) 0.0194(3) Uani 1 1 d . . . C41 C 0.04964(14) 0.32530(4) 0.17400(15) 0.0208(3) Uani 1 1 d . . . H41 H 0.0391 0.2947 0.1834 0.025 Uiso 1 1 calc R . . C42 C -0.03710(14) 0.34666(5) 0.07052(14) 0.0214(3) Uani 1 1 d . . . H42 H -0.1091 0.3316 0.0089 0.026 Uiso 1 1 calc R . . C43 C -0.01679(14) 0.39218(4) 0.05731(14) 0.0194(3) Uani 1 1 d . . . C44 C 0.08859(14) 0.41481(4) 0.14977(14) 0.0185(3) Uani 1 1 d . . . C45 C 0.10939(13) 0.46155(4) 0.12369(14) 0.0182(3) Uani 1 1 d . . . C46 C 0.21860(13) 0.48935(4) 0.21635(13) 0.0186(3) Uani 1 1 d . . . H46 H 0.3121 0.4725 0.2362 0.022 Uiso 1 1 calc R . . C47 C 0.15317(13) 0.49924(4) 0.36458(13) 0.0186(3) Uani 1 1 d . . . H47A H 0.0612 0.5162 0.3446 0.022 Uiso 1 1 calc R . . H47B H 0.1265 0.4713 0.4097 0.022 Uiso 1 1 calc R . . C48 C 0.25571(14) 0.52460(4) 0.47619(14) 0.0188(3) Uani 1 1 d . . . H48 H 0.2866 0.5520 0.4280 0.023 Uiso 1 1 calc R . . C49 C 0.17341(14) 0.53723(4) 0.61049(14) 0.0213(3) Uani 1 1 d . . . H49A H 0.0757 0.5492 0.5762 0.026 Uiso 1 1 calc R . . H49B H 0.1567 0.5106 0.6681 0.026 Uiso 1 1 calc R . . C50 C 0.25421(17) 0.57058(5) 0.71060(16) 0.0297(3) Uani 1 1 d . . . H50A H 0.2720 0.5970 0.6545 0.045 Uiso 1 1 calc R . . H50B H 0.3487 0.5584 0.7501 0.045 Uiso 1 1 calc R . . H50C H 0.1939 0.5778 0.7916 0.045 Uiso 1 1 calc R . . C51 C 0.25281(15) 0.53106(4) 0.13471(14) 0.0228(3) Uani 1 1 d . . . H51A H 0.1634 0.5489 0.1207 0.034 Uiso 1 1 calc R . . H51B H 0.2875 0.5236 0.0389 0.034 Uiso 1 1 calc R . . H51C H 0.3296 0.5475 0.1921 0.034 Uiso 1 1 calc R . . C52 C 0.39424(14) 0.49833(5) 0.52143(15) 0.0245(3) Uani 1 1 d . . . H52A H 0.3664 0.4710 0.5675 0.037 Uiso 1 1 calc R . . H52B H 0.4583 0.5153 0.5914 0.037 Uiso 1 1 calc R . . H52C H 0.4470 0.4918 0.4345 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0291(5) 0.0178(5) 0.0292(5) -0.0019(4) -0.0101(4) 0.0023(4) O2 0.0268(5) 0.0275(5) 0.0238(5) -0.0001(4) -0.0044(4) -0.0057(4) O3 0.0247(5) 0.0257(5) 0.0274(5) -0.0073(4) -0.0017(4) -0.0036(4) N1 0.0212(5) 0.0174(5) 0.0232(6) -0.0007(4) 0.0012(4) 0.0010(4) C1 0.0173(6) 0.0187(6) 0.0248(7) -0.0016(5) 0.0032(5) -0.0004(5) C2 0.0204(6) 0.0212(7) 0.0250(7) 0.0024(5) 0.0065(5) 0.0020(5) C3 0.0187(6) 0.0261(7) 0.0240(7) 0.0053(5) 0.0011(5) -0.0002(5) C4 0.0145(6) 0.0279(7) 0.0211(6) 0.0001(5) 0.0036(5) -0.0032(5) C5 0.0147(6) 0.0223(7) 0.0217(6) -0.0010(5) 0.0025(5) -0.0015(5) C6 0.0137(6) 0.0232(7) 0.0255(7) -0.0053(5) 0.0035(5) -0.0024(5) C7 0.0165(6) 0.0164(6) 0.0291(7) -0.0040(5) -0.0002(5) 0.0000(5) C8 0.0187(6) 0.0220(6) 0.0254(6) -0.0010(5) -0.0005(5) 0.0036(5) C9 0.0263(7) 0.0308(7) 0.0252(7) 0.0012(6) -0.0027(5) 0.0089(6) C10 0.0337(8) 0.0297(7) 0.0283(7) 0.0062(6) -0.0009(6) 0.0016(6) C11 0.0567(10) 0.0278(8) 0.0294(8) 0.0054(6) 0.0015(7) 0.0105(7) C12 0.0226(7) 0.0178(6) 0.0379(8) -0.0065(6) 0.0044(6) -0.0009(5) C13 0.0393(9) 0.0691(12) 0.0301(8) 0.0018(8) -0.0087(7) -0.0106(9) O4 0.0275(5) 0.0173(5) 0.0275(5) 0.0009(4) -0.0087(4) -0.0017(4) O5 0.0235(5) 0.0246(5) 0.0296(5) -0.0050(4) -0.0067(4) -0.0004(4) O6 0.0245(5) 0.0232(5) 0.0321(5) -0.0028(4) -0.0058(4) -0.0041(4) N2 0.0222(6) 0.0172(5) 0.0199(5) -0.0008(4) 0.0003(4) -0.0018(4) C14 0.0213(6) 0.0179(6) 0.0172(6) -0.0006(5) 0.0023(5) 0.0006(5) C15 0.0238(6) 0.0187(6) 0.0196(6) 0.0006(5) 0.0049(5) 0.0025(5) C16 0.0239(7) 0.0243(7) 0.0185(6) 0.0007(5) 0.0016(5) 0.0051(5) C17 0.0190(6) 0.0258(7) 0.0163(6) -0.0038(5) 0.0021(5) 0.0011(5) C18 0.0211(6) 0.0189(6) 0.0171(6) -0.0015(5) 0.0020(5) -0.0005(5) C19 0.0217(6) 0.0189(6) 0.0179(6) -0.0032(5) 0.0020(5) -0.0024(5) C20 0.0230(7) 0.0176(6) 0.0178(6) -0.0006(5) 0.0002(5) -0.0012(5) C21 0.0217(6) 0.0203(6) 0.0178(6) 0.0014(5) 0.0000(5) -0.0017(5) C22 0.0221(6) 0.0204(6) 0.0221(6) 0.0039(5) -0.0014(5) -0.0024(5) C23 0.0242(7) 0.0224(7) 0.0278(7) 0.0049(5) 0.0023(5) 0.0002(5) C24 0.0256(7) 0.0318(8) 0.0432(9) 0.0045(7) 0.0001(6) 0.0030(6) C25 0.0254(7) 0.0186(6) 0.0241(6) -0.0003(5) 0.0040(5) -0.0033(5) C26 0.0260(7) 0.0313(8) 0.0319(8) -0.0018(6) -0.0076(6) -0.0040(6) O7 0.0309(5) 0.0206(5) 0.0279(5) 0.0007(4) -0.0096(4) 0.0029(4) O8 0.0281(5) 0.0177(4) 0.0257(5) -0.0010(4) -0.0064(4) -0.0004(4) O9 0.0277(5) 0.0182(4) 0.0272(5) 0.0047(4) -0.0029(4) 0.0020(4) N3 0.0235(6) 0.0156(5) 0.0192(5) 0.0005(4) 0.0009(4) 0.0003(4) C27 0.0204(6) 0.0214(6) 0.0173(6) 0.0021(5) 0.0018(5) 0.0006(5) C28 0.0238(6) 0.0206(7) 0.0202(6) -0.0019(5) 0.0005(5) -0.0019(5) C29 0.0247(6) 0.0171(6) 0.0204(6) -0.0009(5) 0.0041(5) -0.0013(5) C30 0.0207(6) 0.0174(6) 0.0180(6) 0.0006(5) 0.0044(5) -0.0015(5) C31 0.0204(6) 0.0178(6) 0.0183(6) 0.0016(5) 0.0036(5) -0.0010(5) C32 0.0224(6) 0.0186(6) 0.0179(6) 0.0029(5) 0.0041(5) -0.0007(5) C33 0.0277(7) 0.0156(6) 0.0179(6) -0.0005(5) 0.0024(5) -0.0005(5) C34 0.0280(7) 0.0174(6) 0.0169(6) -0.0001(5) 0.0019(5) -0.0021(5) C35 0.0298(7) 0.0205(6) 0.0193(6) -0.0031(5) 0.0011(5) -0.0020(5) C36 0.0443(9) 0.0356(8) 0.0291(7) -0.0018(7) -0.0007(6) -0.0188(7) C37 0.0833(15) 0.0355(9) 0.0377(9) 0.0051(8) -0.0053(9) -0.0288(9) C38 0.0342(8) 0.0201(6) 0.0271(7) -0.0019(5) 0.0038(6) 0.0035(6) C39 0.0276(7) 0.0272(7) 0.0233(7) -0.0008(6) -0.0016(5) 0.0019(6) O10 0.0267(5) 0.0178(4) 0.0271(5) 0.0001(4) -0.0088(4) 0.0002(4) O11 0.0230(5) 0.0210(5) 0.0278(5) 0.0029(4) -0.0073(4) -0.0001(4) O12 0.0246(5) 0.0193(4) 0.0229(4) 0.0008(4) -0.0038(4) 0.0035(4) N4 0.0204(5) 0.0170(5) 0.0230(5) 0.0017(4) -0.0008(4) 0.0013(4) C40 0.0206(6) 0.0170(6) 0.0208(6) -0.0005(5) 0.0028(5) 0.0020(5) C41 0.0209(6) 0.0169(6) 0.0249(7) -0.0012(5) 0.0046(5) 0.0000(5) C42 0.0183(6) 0.0224(6) 0.0233(6) -0.0024(5) 0.0009(5) -0.0019(5) C43 0.0155(6) 0.0232(7) 0.0197(6) 0.0005(5) 0.0025(5) 0.0034(5) C44 0.0165(6) 0.0198(7) 0.0194(6) -0.0001(5) 0.0023(5) 0.0010(5) C45 0.0151(6) 0.0205(6) 0.0194(6) 0.0000(5) 0.0036(5) 0.0046(5) C46 0.0163(6) 0.0176(6) 0.0218(6) 0.0006(5) 0.0009(5) 0.0013(5) C47 0.0172(6) 0.0173(6) 0.0211(6) 0.0010(5) 0.0002(5) 0.0003(5) C48 0.0171(6) 0.0175(6) 0.0214(6) 0.0013(5) -0.0002(5) -0.0012(5) C49 0.0194(6) 0.0203(6) 0.0239(6) 0.0008(5) 0.0010(5) -0.0007(5) C50 0.0298(7) 0.0314(8) 0.0278(7) -0.0065(6) 0.0009(6) -0.0031(6) C51 0.0238(6) 0.0212(6) 0.0232(6) 0.0037(5) 0.0007(5) -0.0022(5) C52 0.0189(6) 0.0290(7) 0.0251(7) 0.0007(6) -0.0017(5) 0.0022(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2471(16) . ? O2 C4 1.3300(16) . ? O2 H2 0.8400 . ? O3 C6 1.2480(16) . ? N1 C2 1.3503(17) . ? N1 C1 1.3837(17) . ? N1 H1N 0.920(12) . ? C1 C5 1.4457(18) . ? C2 C3 1.3521(19) . ? C2 H2A 0.9500 . ? C3 C4 1.411(2) . ? C3 H3 0.9500 . ? C4 C5 1.4120(18) . ? C5 C6 1.4709(19) . ? C6 C7 1.5139(19) . ? C7 C12 1.5253(18) . ? C7 C8 1.5450(19) . ? C7 H7 1.0000 . ? C8 C9 1.5346(19) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.528(2) . ? C9 C13 1.531(2) . ? C9 H9 1.0000 . ? C10 C11 1.528(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O4 C14 1.2465(16) . ? O5 C17 1.3308(16) . ? O5 H5 0.8400 . ? O6 C19 1.2416(16) . ? N2 C15 1.3501(18) . ? N2 C14 1.3842(17) . ? N2 H2N 0.875(18) . ? C14 C18 1.4459(18) . ? C15 C16 1.351(2) . ? C15 H15 0.9500 . ? C16 C17 1.410(2) . ? C16 H16 0.9500 . ? C17 C18 1.4096(18) . ? C18 C19 1.4734(18) . ? C19 C20 1.5156(18) . ? C20 C25 1.5281(18) . ? C20 C21 1.5500(18) . ? C20 H20 1.0000 . ? C21 C22 1.5364(18) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.532(2) . ? C22 C26 1.5326(19) . ? C22 H22 1.0000 . ? C23 C24 1.526(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? 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 . ? O7 C27 1.3222(16) . ? O7 H7A 0.8400 . ? O8 C30 1.2437(16) . ? O9 C32 1.2451(16) . ? N3 C29 1.3510(17) . ? N3 C30 1.3867(17) . ? N3 H3N 0.922(12) . ? C27 C31 1.4131(18) . ? C27 C28 1.4136(19) . ? C28 C29 1.3526(19) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.4433(18) . ? C31 C32 1.4679(18) . ? C32 C33 1.5202(17) . ? C33 C38 1.5273(18) . ? C33 C34 1.5458(19) . ? C33 H33 1.0000 . ? C34 C35 1.5385(17) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.525(2) . ? C35 C39 1.5276(19) . ? C35 H35 1.0000 . ? C36 C37 1.521(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? O10 C40 1.2428(16) . ? O11 C43 1.3249(16) . ? O11 H11 0.8400 . ? O12 C45 1.2497(15) . ? N4 C41 1.3492(17) . ? N4 C40 1.3860(18) . ? N4 H4N 0.918(12) . ? C40 C44 1.4464(18) . ? C41 C42 1.3534(19) . ? C41 H41 0.9500 . ? C42 C43 1.4158(19) . ? C42 H42 0.9500 . ? C43 C44 1.4109(18) . ? C44 C45 1.4688(19) . ? C45 C46 1.5174(17) . ? C46 C51 1.5259(18) . ? C46 C47 1.5509(18) . ? C46 H46 1.0000 . ? C47 C48 1.5393(16) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C52 1.5259(18) . ? C48 C49 1.5355(18) . ? C48 H48 1.0000 . ? C49 C50 1.5238(19) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 H2 109.5 . . ? C2 N1 C1 123.95(12) . . ? C2 N1 H1N 117.7(10) . . ? C1 N1 H1N 118.3(10) . . ? O1 C1 N1 117.97(12) . . ? O1 C1 C5 125.95(12) . . ? N1 C1 C5 116.07(11) . . ? N1 C2 C3 122.07(12) . . ? N1 C2 H2A 119.0 . . ? C3 C2 H2A 119.0 . . ? C2 C3 C4 117.53(12) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? O2 C4 C3 116.35(12) . . ? O2 C4 C5 122.03(12) . . ? C3 C4 C5 121.63(12) . . ? C4 C5 C1 118.35(12) . . ? C4 C5 C6 118.68(11) . . ? C1 C5 C6 122.92(12) . . ? O3 C6 C5 118.85(12) . . ? O3 C6 C7 118.33(11) . . ? C5 C6 C7 122.69(11) . . ? C6 C7 C12 110.68(11) . . ? C6 C7 C8 106.41(10) . . ? C12 C7 C8 112.39(11) . . ? C6 C7 H7 109.1 . . ? C12 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C9 C8 C7 116.39(11) . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C13 110.98(13) . . ? C10 C9 C8 109.27(11) . . ? C13 C9 C8 110.61(13) . . ? C10 C9 H9 108.6 . . ? C13 C9 H9 108.6 . . ? C8 C9 H9 108.6 . . ? C9 C10 C11 115.36(13) . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? 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 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 O5 H5 109.5 . . ? C15 N2 C14 123.91(12) . . ? C15 N2 H2N 121.4(11) . . ? C14 N2 H2N 114.6(11) . . ? O4 C14 N2 118.04(12) . . ? O4 C14 C18 125.90(12) . . ? N2 C14 C18 116.05(12) . . ? N2 C15 C16 121.99(12) . . ? N2 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C17 117.69(12) . . ? C15 C16 H16 121.2 . . ? C17 C16 H16 121.2 . . ? O5 C17 C18 121.68(12) . . ? O5 C17 C16 116.68(12) . . ? C18 C17 C16 121.65(12) . . ? C17 C18 C14 118.39(12) . . ? C17 C18 C19 119.08(11) . . ? C14 C18 C19 122.51(11) . . ? O6 C19 C18 118.49(12) . . ? O6 C19 C20 118.48(11) . . ? C18 C19 C20 122.91(11) . . ? C19 C20 C25 110.35(11) . . ? C19 C20 C21 106.53(10) . . ? C25 C20 C21 112.23(11) . . ? C19 C20 H20 109.2 . . ? C25 C20 H20 109.2 . . ? C21 C20 H20 109.2 . . ? C22 C21 C20 116.17(10) . . ? C22 C21 H21A 108.2 . . ? C20 C21 H21A 108.2 . . ? C22 C21 H21B 108.2 . . ? C20 C21 H21B 108.2 . . ? H21A C21 H21B 107.4 . . ? C23 C22 C26 111.22(12) . . ? C23 C22 C21 109.94(10) . . ? C26 C22 C21 111.32(11) . . ? C23 C22 H22 108.1 . . ? C26 C22 H22 108.1 . . ? C21 C22 H22 108.1 . . ? C24 C23 C22 113.77(12) . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23B 108.8 . . ? C22 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? 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 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C27 O7 H7A 109.5 . . ? C29 N3 C30 124.09(11) . . ? C29 N3 H3N 120.4(10) . . ? C30 N3 H3N 115.5(10) . . ? O7 C27 C31 122.13(11) . . ? O7 C27 C28 116.49(12) . . ? C31 C27 C28 121.37(12) . . ? C29 C28 C27 118.07(12) . . ? C29 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? N3 C29 C28 121.73(12) . . ? N3 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? O8 C30 N3 117.89(11) . . ? O8 C30 C31 125.96(12) . . ? N3 C30 C31 116.15(11) . . ? C27 C31 C30 118.55(11) . . ? C27 C31 C32 118.41(11) . . ? C30 C31 C32 122.92(11) . . ? O9 C32 C31 118.45(11) . . ? O9 C32 C33 117.68(11) . . ? C31 C32 C33 123.85(11) . . ? C32 C33 C38 109.68(11) . . ? C32 C33 C34 109.81(10) . . ? C38 C33 C34 110.61(11) . . ? C32 C33 H33 108.9 . . ? C38 C33 H33 108.9 . . ? C34 C33 H33 108.9 . . ? C35 C34 C33 113.73(10) . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34B 108.8 . . ? C33 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C36 C35 C39 110.70(12) . . ? C36 C35 C34 112.52(11) . . ? C39 C35 C34 110.99(11) . . ? C36 C35 H35 107.5 . . ? C39 C35 H35 107.5 . . ? C34 C35 H35 107.5 . . ? C37 C36 C35 114.65(15) . . ? C37 C36 H36A 108.6 . . ? C35 C36 H36A 108.6 . . ? C37 C36 H36B 108.6 . . ? C35 C36 H36B 108.6 . . ? H36A C36 H36B 107.6 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C33 C38 H38A 109.5 . . ? C33 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C33 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C35 C39 H39A 109.5 . . ? C35 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C35 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C43 O11 H11 109.5 . . ? C41 N4 C40 124.27(11) . . ? C41 N4 H4N 119.3(10) . . ? C40 N4 H4N 115.9(10) . . ? O10 C40 N4 118.13(11) . . ? O10 C40 C44 126.08(12) . . ? N4 C40 C44 115.79(11) . . ? N4 C41 C42 122.00(12) . . ? N4 C41 H41 119.0 . . ? C42 C41 H41 119.0 . . ? C41 C42 C43 117.70(12) . . ? C41 C42 H42 121.2 . . ? C43 C42 H42 121.2 . . ? O11 C43 C44 122.39(12) . . ? O11 C43 C42 116.14(11) . . ? C44 C43 C42 121.46(12) . . ? C43 C44 C40 118.77(12) . . ? C43 C44 C45 118.28(11) . . ? C40 C44 C45 122.84(11) . . ? O12 C45 C44 118.87(11) . . ? O12 C45 C46 118.06(11) . . ? C44 C45 C46 123.07(11) . . ? C45 C46 C51 110.39(10) . . ? C45 C46 C47 108.60(10) . . ? C51 C46 C47 111.66(11) . . ? C45 C46 H46 108.7 . . ? C51 C46 H46 108.7 . . ? C47 C46 H46 108.7 . . ? C48 C47 C46 115.11(10) . . ? C48 C47 H47A 108.5 . . ? C46 C47 H47A 108.5 . . ? C48 C47 H47B 108.5 . . ? C46 C47 H47B 108.5 . . ? H47A C47 H47B 107.5 . . ? C52 C48 C49 111.09(11) . . ? C52 C48 C47 110.97(10) . . ? C49 C48 C47 110.47(10) . . ? C52 C48 H48 108.1 . . ? C49 C48 H48 108.1 . . ? C47 C48 H48 108.1 . . ? C50 C49 C48 114.04(11) . . ? C50 C49 H49A 108.7 . . ? C48 C49 H49A 108.7 . . ? C50 C49 H49B 108.7 . . ? C48 C49 H49B 108.7 . . ? H49A C49 H49B 107.6 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C46 C51 H51A 109.5 . . ? C46 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C46 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C48 C52 H52A 109.5 . . ? C48 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C48 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 176.94(12) . . . . ? C2 N1 C1 C5 -4.27(19) . . . . ? C1 N1 C2 C3 2.3(2) . . . . ? N1 C2 C3 C4 3.52(19) . . . . ? C2 C3 C4 O2 172.89(11) . . . . ? C2 C3 C4 C5 -7.13(19) . . . . ? O2 C4 C5 C1 -174.97(12) . . . . ? C3 C4 C5 C1 5.05(18) . . . . ? O2 C4 C5 C6 2.54(18) . . . . ? C3 C4 C5 C6 -177.44(12) . . . . ? O1 C1 C5 C4 179.26(12) . . . . ? N1 C1 C5 C4 0.57(17) . . . . ? O1 C1 C5 C6 1.9(2) . . . . ? N1 C1 C5 C6 -176.83(12) . . . . ? C4 C5 C6 O3 -6.48(18) . . . . ? C1 C5 C6 O3 170.91(12) . . . . ? C4 C5 C6 C7 169.28(11) . . . . ? C1 C5 C6 C7 -13.3(2) . . . . ? O3 C6 C7 C12 -28.55(16) . . . . ? C5 C6 C7 C12 155.67(12) . . . . ? O3 C6 C7 C8 93.83(14) . . . . ? C5 C6 C7 C8 -81.95(14) . . . . ? C6 C7 C8 C9 169.96(11) . . . . ? C12 C7 C8 C9 -68.75(15) . . . . ? C7 C8 C9 C10 165.91(11) . . . . ? C7 C8 C9 C13 -71.64(16) . . . . ? C13 C9 C10 C11 60.18(18) . . . . ? C8 C9 C10 C11 -177.59(12) . . . . ? C15 N2 C14 O4 176.61(12) . . . . ? C15 N2 C14 C18 -4.82(19) . . . . ? C14 N2 C15 C16 2.8(2) . . . . ? N2 C15 C16 C17 2.63(19) . . . . ? C15 C16 C17 O5 174.38(12) . . . . ? C15 C16 C17 C18 -5.79(19) . . . . ? O5 C17 C18 C14 -176.52(12) . . . . ? C16 C17 C18 C14 3.65(18) . . . . ? O5 C17 C18 C19 1.71(18) . . . . ? C16 C17 C18 C19 -178.12(12) . . . . ? O4 C14 C18 C17 179.96(12) . . . . ? N2 C14 C18 C17 1.52(17) . . . . ? O4 C14 C18 C19 1.8(2) . . . . ? N2 C14 C18 C19 -176.64(12) . . . . ? C17 C18 C19 O6 -5.38(18) . . . . ? C14 C18 C19 O6 172.77(12) . . . . ? C17 C18 C19 C20 170.66(11) . . . . ? C14 C18 C19 C20 -11.19(19) . . . . ? O6 C19 C20 C25 -23.01(16) . . . . ? C18 C19 C20 C25 160.95(11) . . . . ? O6 C19 C20 C21 99.06(13) . . . . ? C18 C19 C20 C21 -76.97(14) . . . . ? C19 C20 C21 C22 168.89(11) . . . . ? C25 C20 C21 C22 -70.23(14) . . . . ? C20 C21 C22 C23 163.34(11) . . . . ? C20 C21 C22 C26 -72.95(14) . . . . ? C26 C22 C23 C24 67.81(15) . . . . ? C21 C22 C23 C24 -168.43(12) . . . . ? O7 C27 C28 C29 178.78(12) . . . . ? C31 C27 C28 C29 -0.3(2) . . . . ? C30 N3 C29 C28 -0.17(19) . . . . ? C27 C28 C29 N3 0.99(19) . . . . ? C29 N3 C30 O8 178.82(11) . . . . ? C29 N3 C30 C31 -1.25(18) . . . . ? O7 C27 C31 C30 179.86(12) . . . . ? C28 C27 C31 C30 -1.08(19) . . . . ? O7 C27 C31 C32 -3.83(18) . . . . ? C28 C27 C31 C32 175.23(12) . . . . ? O8 C30 C31 C27 -178.27(12) . . . . ? N3 C30 C31 C27 1.80(17) . . . . ? O8 C30 C31 C32 5.6(2) . . . . ? N3 C30 C31 C32 -174.33(11) . . . . ? C27 C31 C32 O9 3.04(18) . . . . ? C30 C31 C32 O9 179.19(11) . . . . ? C27 C31 C32 C33 -175.19(11) . . . . ? C30 C31 C32 C33 0.95(19) . . . . ? O9 C32 C33 C38 -19.66(16) . . . . ? C31 C32 C33 C38 158.58(12) . . . . ? O9 C32 C33 C34 102.08(13) . . . . ? C31 C32 C33 C34 -79.67(15) . . . . ? C32 C33 C34 C35 171.43(10) . . . . ? C38 C33 C34 C35 -67.39(14) . . . . ? C33 C34 C35 C36 158.47(13) . . . . ? C33 C34 C35 C39 -76.86(14) . . . . ? C39 C35 C36 C37 164.99(13) . . . . ? C34 C35 C36 C37 -70.17(17) . . . . ? C41 N4 C40 O10 179.78(12) . . . . ? C41 N4 C40 C44 -0.30(18) . . . . ? C40 N4 C41 C42 -0.6(2) . . . . ? N4 C41 C42 C43 1.20(19) . . . . ? C41 C42 C43 O11 178.60(11) . . . . ? C41 C42 C43 C44 -0.86(19) . . . . ? O11 C43 C44 C40 -179.46(11) . . . . ? C42 C43 C44 C40 -0.04(18) . . . . ? O11 C43 C44 C45 -3.00(18) . . . . ? C42 C43 C44 C45 176.43(12) . . . . ? O10 C40 C44 C43 -179.49(12) . . . . ? N4 C40 C44 C43 0.60(17) . . . . ? O10 C40 C44 C45 4.2(2) . . . . ? N4 C40 C44 C45 -175.69(11) . . . . ? C43 C44 C45 O12 -0.25(17) . . . . ? C40 C44 C45 O12 176.06(11) . . . . ? C43 C44 C45 C46 179.61(11) . . . . ? C40 C44 C45 C46 -4.08(18) . . . . ? O12 C45 C46 C51 -19.21(15) . . . . ? C44 C45 C46 C51 160.92(11) . . . . ? O12 C45 C46 C47 103.51(12) . . . . ? C44 C45 C46 C47 -76.36(14) . . . . ? C45 C46 C47 C48 175.87(10) . . . . ? C51 C46 C47 C48 -62.18(13) . . . . ? C46 C47 C48 C52 -63.08(14) . . . . ? C46 C47 C48 C49 173.25(10) . . . . ? C52 C48 C49 C50 69.08(14) . . . . ? C47 C48 C49 C50 -167.32(11) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 66.81 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.122 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 941139'