# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 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_2004uv02cj02bn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2004uv02cj02b _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 N2 O4' _chemical_formula_sum 'C26 H26 N2 O4' _chemical_formula_weight 430.49 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4099(2) _cell_length_b 5.3783(2) _cell_length_c 23.8999(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.092(2) _cell_angle_gamma 90.00 _cell_volume 1064.29(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1841 _cell_measurement_theta_min 0.883 _cell_measurement_theta_max 68.251 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7190 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD2000 _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 14 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2899 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 68.31 _reflns_number_total 2899 _reflns_number_gt 2847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Bruker Xprep' _computing_structure_solution 'SIR97 (Altomare et all, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.8759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(4) _refine_ls_number_reflns 2899 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O11 O 0.4133(2) 0.9390(5) 0.27775(9) 0.0384(6) Uani 1 1 d . . . C1 C 0.4728(3) 1.1431(6) 0.26979(11) 0.0294(6) Uani 1 1 d . . . C2 C 0.6430(3) 1.1664(6) 0.25630(11) 0.0304(7) Uani 1 1 d . . . H2 H 0.6774 1.3440 0.2618 0.036 Uiso 1 1 calc R . . C3 C 0.6480(3) 1.0944(6) 0.19490(11) 0.0285(7) Uani 1 1 d . . . C4 C 0.5657(3) 0.8828(6) 0.16926(11) 0.0317(7) Uani 1 1 d . . . H4 H 0.5038 0.7836 0.1904 0.038 Uiso 1 1 calc R . . C5 C 0.5742(3) 0.8186(7) 0.11400(11) 0.0318(7) Uani 1 1 d . . . H5 H 0.5169 0.6768 0.0975 0.038 Uiso 1 1 calc R . . C6 C 0.6665(3) 0.9594(6) 0.08136(11) 0.0284(6) Uani 1 1 d . . . C7 C 0.6746(3) 0.8964(6) 0.02401(11) 0.0282(6) Uani 1 1 d . . . H7 H 0.6167 0.7570 0.0065 0.034 Uiso 1 1 calc R . . C8 C 0.7661(3) 1.0373(6) -0.00556(11) 0.0288(7) Uani 1 1 d . . . C9 C 0.8540(3) 1.2442(6) 0.02031(12) 0.0312(7) Uani 1 1 d . . . H9 H 0.9185 1.3392 -0.0007 0.037 Uiso 1 1 calc R . . C10 C 0.8472(3) 1.3085(6) 0.07493(12) 0.0308(7) Uani 1 1 d . . . H10 H 0.9072 1.4473 0.0918 0.037 Uiso 1 1 calc R . . C11 C 0.7509(3) 1.1691(6) 0.10686(11) 0.0277(6) Uani 1 1 d . . . C12 C 0.7383(3) 1.2330(6) 0.16386(11) 0.0298(7) Uani 1 1 d . . . H12 H 0.7940 1.3754 0.1808 0.036 Uiso 1 1 calc R . . N13 N 0.3927(3) 1.3584(5) 0.27127(10) 0.0308(6) Uani 1 1 d . . . C14 C 0.2341(4) 1.3749(7) 0.28672(13) 0.0382(8) Uani 1 1 d . . . H14 H 0.1849 1.2052 0.2831 0.046 Uiso 1 1 calc R . . C15 C 0.2446(4) 1.4612(8) 0.34920(14) 0.0483(9) Uani 1 1 d . . . H15A H 0.2874 1.6330 0.3530 0.058 Uiso 1 1 calc R . . H15B H 0.1348 1.4633 0.3588 0.058 Uiso 1 1 calc R . . C16 C 0.3500(5) 1.2973(7) 0.39011(14) 0.0526(10) Uani 1 1 d . . . C17 C 0.5240(5) 1.3177(8) 0.40754(12) 0.0517(10) Uani 1 1 d . . . C18 C 0.6392(5) 1.4904(7) 0.39670(12) 0.0485(9) Uani 1 1 d . . . H18 H 0.6085 1.6289 0.3725 0.058 Uiso 1 1 calc R . . C19 C 0.7990(5) 1.4553(9) 0.42197(14) 0.0634(12) Uani 1 1 d . . . H19 H 0.8798 1.5699 0.4155 0.076 Uiso 1 1 calc R . . C20 C 0.8409(8) 1.2432(11) 0.45811(16) 0.088(2) Uani 1 1 d . . . H20 H 0.9506 1.2200 0.4752 0.106 Uiso 1 1 calc R . . C21 C 0.7281(10) 1.0723(11) 0.46888(16) 0.096(2) Uani 1 1 d . . . H21 H 0.7582 0.9329 0.4928 0.116 Uiso 1 1 calc R . . C22 C 0.5697(7) 1.1114(9) 0.44356(13) 0.0730(15) Uani 1 1 d . . . N23 N 0.4322(7) 0.9789(8) 0.44801(14) 0.0918(16) Uani 1 1 d . . . H23 H 0.4287 0.8434 0.4684 0.110 Uiso 1 1 calc R . . C24 C 0.3036(7) 1.0906(8) 0.41600(18) 0.0748(15) Uani 1 1 d . . . H24 H 0.1955 1.0327 0.4121 0.090 Uiso 1 1 calc R . . C82 C 0.7089(3) 0.7834(6) -0.08863(12) 0.0341(7) Uani 1 1 d . . . H82A H 0.7510 0.6349 -0.0673 0.051 Uiso 1 1 calc R . . H82B H 0.7324 0.7735 -0.1273 0.051 Uiso 1 1 calc R . . H82C H 0.5918 0.7933 -0.0902 0.051 Uiso 1 1 calc R . . C141 C 0.1226(4) 1.5483(7) 0.24849(15) 0.0449(9) Uani 1 1 d . . . O142 O 0.1723(2) 1.6053(5) 0.20045(9) 0.0388(5) Uani 1 1 d . . . C143 C 0.0838(4) 1.8028(7) 0.16721(15) 0.0476(9) Uani 1 1 d . . . H14A H -0.0324 1.7758 0.1649 0.071 Uiso 1 1 calc R . . H14B H 0.1102 1.8028 0.1289 0.071 Uiso 1 1 calc R . . H14C H 0.1139 1.9633 0.1855 0.071 Uiso 1 1 calc R . . O144 O -0.0015(3) 1.6258(7) 0.26026(13) 0.0760(10) Uani 1 1 d . . . C211 C 0.7607(4) 1.0060(7) 0.29793(11) 0.0395(8) Uani 1 1 d . . . H21A H 0.7304 0.8305 0.2926 0.059 Uiso 1 1 calc R . . H21B H 0.7558 1.0559 0.3370 0.059 Uiso 1 1 calc R . . H21C H 0.8708 1.0295 0.2906 0.059 Uiso 1 1 calc R . . O81 O 0.7839(2) 0.9998(4) -0.06105(7) 0.0317(5) Uani 1 1 d . . . H13 H 0.445(4) 1.499(8) 0.2680(13) 0.038(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0448(12) 0.0255(14) 0.0477(12) -0.0015(10) 0.0162(9) 0.0012(11) C1 0.0354(14) 0.0235(18) 0.0290(12) 0.0004(13) 0.0047(10) 0.0029(15) C2 0.0320(13) 0.0244(18) 0.0344(13) -0.0021(13) 0.0049(10) 0.0045(13) C3 0.0267(12) 0.0233(18) 0.0345(13) 0.0021(12) 0.0029(10) 0.0052(13) C4 0.0318(13) 0.029(2) 0.0347(14) 0.0032(13) 0.0064(10) 0.0018(13) C5 0.0334(13) 0.0247(18) 0.0359(13) -0.0022(13) 0.0023(11) -0.0040(13) C6 0.0237(12) 0.0259(18) 0.0348(13) 0.0011(12) 0.0028(10) 0.0023(13) C7 0.0263(12) 0.0211(17) 0.0358(13) -0.0013(12) 0.0017(10) -0.0008(12) C8 0.0217(12) 0.0314(19) 0.0330(12) 0.0018(12) 0.0040(10) 0.0063(12) C9 0.0250(12) 0.0292(19) 0.0401(14) 0.0032(13) 0.0078(10) -0.0005(13) C10 0.0234(12) 0.0267(18) 0.0415(14) -0.0034(14) 0.0039(10) -0.0035(13) C11 0.0216(11) 0.0259(18) 0.0352(13) 0.0002(12) 0.0034(9) 0.0026(12) C12 0.0240(12) 0.0271(18) 0.0369(13) -0.0033(12) 0.0011(10) 0.0016(12) N13 0.0348(13) 0.0236(17) 0.0362(12) -0.0005(11) 0.0124(9) 0.0033(12) C14 0.0402(15) 0.029(2) 0.0507(17) -0.0033(15) 0.0228(13) 0.0038(14) C15 0.064(2) 0.035(2) 0.0540(18) -0.0062(17) 0.0340(16) 0.0015(18) C16 0.095(3) 0.031(2) 0.0418(16) -0.0009(16) 0.0388(18) 0.004(2) C17 0.106(3) 0.030(2) 0.0219(13) 0.0010(14) 0.0182(15) 0.015(2) C18 0.082(2) 0.034(2) 0.0272(13) -0.0023(14) 0.0037(14) 0.016(2) C19 0.086(3) 0.055(3) 0.0416(17) -0.0205(19) -0.0093(17) 0.025(2) C20 0.134(5) 0.079(4) 0.0368(19) -0.030(2) -0.025(2) 0.069(4) C21 0.211(7) 0.047(3) 0.0277(18) -0.0039(19) 0.013(3) 0.044(4) C22 0.158(5) 0.039(3) 0.0218(14) 0.0037(16) 0.016(2) 0.042(3) N23 0.213(5) 0.031(2) 0.0499(19) 0.0116(17) 0.073(3) 0.010(3) C24 0.153(4) 0.028(3) 0.061(2) 0.003(2) 0.066(3) 0.003(3) C82 0.0361(14) 0.029(2) 0.0370(14) -0.0033(13) 0.0047(11) 0.0044(14) C141 0.0376(16) 0.034(2) 0.0640(19) -0.0086(17) 0.0124(14) 0.0080(16) O142 0.0337(10) 0.0298(14) 0.0523(11) -0.0012(11) 0.0056(8) 0.0072(10) C143 0.0453(17) 0.030(2) 0.0612(19) -0.0043(17) -0.0091(15) 0.0107(16) O144 0.0546(14) 0.089(3) 0.0916(19) 0.004(2) 0.0321(13) 0.0358(19) C211 0.0445(16) 0.042(2) 0.0309(13) -0.0032(14) 0.0026(11) 0.0144(16) O81 0.0296(9) 0.0325(13) 0.0330(9) -0.0011(9) 0.0058(7) 0.0004(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 O11 C1 1.234(4) . ? C1 N13 1.343(4) . ? C1 C2 1.527(4) . ? C2 C3 1.525(4) . ? C2 C211 1.539(4) . ? C2 H2 1.0000 . ? C3 C12 1.372(4) . ? C3 C4 1.415(4) . ? C4 C5 1.379(4) . ? C4 H4 0.9500 . ? C5 C6 1.413(4) . ? C5 H5 0.9500 . ? C6 C11 1.412(4) . ? C6 C7 1.425(4) . ? C7 C8 1.363(4) . ? C7 H7 0.9500 . ? C8 O81 1.375(3) . ? C8 C9 1.416(4) . ? C9 C10 1.361(4) . ? C9 H9 0.9500 . ? C10 C11 1.420(4) . ? C10 H10 0.9500 . ? C11 C12 1.427(4) . ? C12 H12 0.9500 . ? N13 C14 1.448(3) . ? N13 H13 0.88(4) . ? C14 C141 1.511(5) . ? C14 C15 1.551(4) . ? C14 H14 1.0000 . ? C15 C16 1.488(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C24 1.362(5) . ? C16 C17 1.454(6) . ? C17 C18 1.399(6) . ? C17 C22 1.415(5) . ? C18 C19 1.387(5) . ? C18 H18 0.9500 . ? C19 C20 1.437(7) . ? C19 H19 0.9500 . ? C20 C21 1.378(8) . ? C20 H20 0.9500 . ? C21 C22 1.379(8) . ? C21 H21 0.9500 . ? C22 N23 1.378(7) . ? N23 C24 1.351(7) . ? N23 H23 0.8800 . ? C24 H24 0.9500 . ? C82 O81 1.429(4) . ? C82 H82A 0.9800 . ? C82 H82B 0.9800 . ? C82 H82C 0.9800 . ? C141 O144 1.202(4) . ? C141 O142 1.325(4) . ? O142 C143 1.451(4) . ? C143 H14A 0.9800 . ? C143 H14B 0.9800 . ? C143 H14C 0.9800 . ? C211 H21A 0.9800 . ? C211 H21B 0.9800 . ? C211 H21C 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 O11 C1 N13 123.0(3) . . ? O11 C1 C2 121.7(3) . . ? N13 C1 C2 115.3(3) . . ? C3 C2 C1 111.5(2) . . ? C3 C2 C211 110.9(2) . . ? C1 C2 C211 109.8(2) . . ? C3 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? C211 C2 H2 108.2 . . ? C12 C3 C4 118.6(2) . . ? C12 C3 C2 119.6(3) . . ? C4 C3 C2 121.8(3) . . ? C5 C4 C3 120.8(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C11 C6 C5 118.2(2) . . ? C11 C6 C7 120.0(2) . . ? C5 C6 C7 121.8(3) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 O81 125.8(3) . . ? C7 C8 C9 120.6(2) . . ? O81 C8 C9 113.6(2) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 118.7(2) . . ? C6 C11 C12 119.3(2) . . ? C10 C11 C12 122.0(3) . . ? C3 C12 C11 121.7(3) . . ? C3 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C1 N13 C14 123.2(3) . . ? C1 N13 H13 119(2) . . ? C14 N13 H13 117(2) . . ? N13 C14 C141 112.7(3) . . ? N13 C14 C15 111.3(3) . . ? C141 C14 C15 108.8(3) . . ? N13 C14 H14 108.0 . . ? C141 C14 H14 108.0 . . ? C15 C14 H14 108.0 . . ? C16 C15 C14 112.5(3) . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C24 C16 C17 106.6(4) . . ? C24 C16 C15 126.7(4) . . ? C17 C16 C15 126.7(3) . . ? C18 C17 C22 120.7(4) . . ? C18 C17 C16 133.8(3) . . ? C22 C17 C16 105.5(4) . . ? C19 C18 C17 118.6(4) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 119.1(5) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C21 C20 C19 122.5(5) . . ? C21 C20 H20 118.7 . . ? C19 C20 H20 118.7 . . ? C22 C21 C20 117.4(5) . . ? C22 C21 H21 121.3 . . ? C20 C21 H21 121.3 . . ? C21 C22 N23 130.2(5) . . ? C21 C22 C17 121.6(6) . . ? N23 C22 C17 108.1(4) . . ? C24 N23 C22 109.0(4) . . ? C24 N23 H23 125.5 . . ? C22 N23 H23 125.5 . . ? N23 C24 C16 110.8(5) . . ? N23 C24 H24 124.6 . . ? C16 C24 H24 124.6 . . ? O81 C82 H82A 109.5 . . ? O81 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? O81 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? O144 C141 O142 122.8(3) . . ? O144 C141 C14 123.0(3) . . ? O142 C141 C14 114.2(2) . . ? C141 O142 C143 115.7(3) . . ? O142 C143 H14A 109.5 . . ? O142 C143 H14B 109.5 . . ? H14A C143 H14B 109.5 . . ? O142 C143 H14C 109.5 . . ? H14A C143 H14C 109.5 . . ? H14B C143 H14C 109.5 . . ? C2 C211 H21A 109.5 . . ? C2 C211 H21B 109.5 . . ? H21A C211 H21B 109.5 . . ? C2 C211 H21C 109.5 . . ? H21A C211 H21C 109.5 . . ? H21B C211 H21C 109.5 . . ? C8 O81 C82 116.8(2) . . ? 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 O11 C1 C2 C3 76.1(3) . . . . ? N13 C1 C2 C3 -102.8(3) . . . . ? O11 C1 C2 C211 -47.2(4) . . . . ? N13 C1 C2 C211 133.9(3) . . . . ? C1 C2 C3 C12 138.6(3) . . . . ? C211 C2 C3 C12 -98.8(3) . . . . ? C1 C2 C3 C4 -43.4(4) . . . . ? C211 C2 C3 C4 79.2(3) . . . . ? C12 C3 C4 C5 -0.8(4) . . . . ? C2 C3 C4 C5 -178.8(3) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C11 0.1(4) . . . . ? C4 C5 C6 C7 -179.2(3) . . . . ? C11 C6 C7 C8 1.0(4) . . . . ? C5 C6 C7 C8 -179.6(3) . . . . ? C6 C7 C8 O81 -179.4(2) . . . . ? C6 C7 C8 C9 0.5(4) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? O81 C8 C9 C10 179.0(3) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C5 C6 C11 C10 178.5(3) . . . . ? C7 C6 C11 C10 -2.1(4) . . . . ? C5 C6 C11 C12 -0.9(4) . . . . ? C7 C6 C11 C12 178.5(3) . . . . ? C9 C10 C11 C6 1.8(4) . . . . ? C9 C10 C11 C12 -178.9(3) . . . . ? C4 C3 C12 C11 0.0(4) . . . . ? C2 C3 C12 C11 178.1(2) . . . . ? C6 C11 C12 C3 0.8(4) . . . . ? C10 C11 C12 C3 -178.5(3) . . . . ? O11 C1 N13 C14 5.0(4) . . . . ? C2 C1 N13 C14 -176.1(2) . . . . ? C1 N13 C14 C141 -137.1(3) . . . . ? C1 N13 C14 C15 100.3(3) . . . . ? N13 C14 C15 C16 -56.3(4) . . . . ? C141 C14 C15 C16 178.9(3) . . . . ? C14 C15 C16 C24 -89.4(4) . . . . ? C14 C15 C16 C17 86.5(4) . . . . ? C24 C16 C17 C18 -178.0(3) . . . . ? C15 C16 C17 C18 5.4(6) . . . . ? C24 C16 C17 C22 0.5(4) . . . . ? C15 C16 C17 C22 -176.0(3) . . . . ? C22 C17 C18 C19 0.0(5) . . . . ? C16 C17 C18 C19 178.4(3) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C21 -0.1(6) . . . . ? C19 C20 C21 C22 -0.2(6) . . . . ? C20 C21 C22 N23 -177.5(4) . . . . ? C20 C21 C22 C17 0.4(6) . . . . ? C18 C17 C22 C21 -0.4(5) . . . . ? C16 C17 C22 C21 -179.1(3) . . . . ? C18 C17 C22 N23 178.0(3) . . . . ? C16 C17 C22 N23 -0.8(4) . . . . ? C21 C22 N23 C24 178.9(4) . . . . ? C17 C22 N23 C24 0.8(4) . . . . ? C22 N23 C24 C16 -0.4(4) . . . . ? C17 C16 C24 N23 -0.1(4) . . . . ? C15 C16 C24 N23 176.5(3) . . . . ? N13 C14 C141 O144 -165.0(4) . . . . ? C15 C14 C141 O144 -41.0(5) . . . . ? N13 C14 C141 O142 15.8(4) . . . . ? C15 C14 C141 O142 139.8(3) . . . . ? O144 C141 O142 C143 10.9(5) . . . . ? C14 C141 O142 C143 -170.0(3) . . . . ? C7 C8 O81 C82 -4.7(4) . . . . ? C9 C8 O81 C82 175.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 68.31 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.360 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 662957' ####################################################################### # # 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_2004uv03 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N2 O4' _chemical_formula_weight 430.49 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8210(5) _cell_length_b 5.9160(3) _cell_length_c 22.9298(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.223(4) _cell_angle_gamma 90.00 _cell_volume 1058.06(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.740 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7414 _exptl_absorpt_correction_T_max 0.9639 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 68.65 _reflns_number_total 3829 _reflns_number_gt 3490 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0697P)^2^+0.3806P] 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 0.0(3) _refine_ls_number_reflns 3829 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 1.795 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0636(3) 0.2931(5) 0.80555(10) 0.0342(6) Uani 1 1 d . . . C2 C 0.1579(3) 0.4320(5) 0.84339(11) 0.0362(6) Uani 1 1 d . . . H2 H 0.1988 0.5717 0.8294 0.043 Uiso 1 1 calc R . . C3 C 0.1963(3) 0.3724(4) 0.90315(11) 0.0331(6) Uani 1 1 d . . . C4 C 0.2961(3) 0.5138(5) 0.94233(11) 0.0363(6) Uani 1 1 d . . . H4 H 0.3377 0.6540 0.9290 0.044 Uiso 1 1 calc R . . C5 C 0.3329(3) 0.4498(5) 0.99920(11) 0.0367(6) Uani 1 1 d . . . H5 H 0.4008 0.5452 1.0249 0.044 Uiso 1 1 calc R . . C6 C 0.2706(3) 0.2426(5) 1.02001(10) 0.0345(6) Uani 1 1 d . . . C7 C 0.1719(3) 0.1033(5) 0.98405(11) 0.0350(6) Uani 1 1 d . . . H7 H 0.1290 -0.0341 0.9987 0.042 Uiso 1 1 calc R . . C8 C 0.1334(3) 0.1647(5) 0.92438(11) 0.0340(6) Uani 1 1 d . . . C9 C 0.0352(3) 0.0232(5) 0.88454(10) 0.0369(6) Uani 1 1 d . . . H9 H -0.0084 -0.1160 0.8978 0.044 Uiso 1 1 calc R . . C10 C 0.0029(3) 0.0853(5) 0.82735(11) 0.0377(6) Uani 1 1 d . . . H10 H -0.0619 -0.0130 0.8015 0.045 Uiso 1 1 calc R . . O11 O 0.3191(2) 0.2022(3) 1.07786(7) 0.0381(4) Uani 1 1 d . . . C12 C 0.2771(4) -0.0124(5) 1.10121(11) 0.0421(6) Uani 1 1 d . . . H12A H 0.1522 -0.0295 1.0995 0.063 Uiso 1 1 calc R . . H12B H 0.3240 -0.0228 1.1420 0.063 Uiso 1 1 calc R . . H12C H 0.3263 -0.1325 1.0782 0.063 Uiso 1 1 calc R . . C13 C 0.0208(3) 0.3479(5) 0.74122(11) 0.0363(6) Uani 1 1 d . . . H13 H 0.0472 0.2109 0.7180 0.044 Uiso 1 1 calc R . . C14 C -0.1690(3) 0.4022(6) 0.72839(12) 0.0448(7) Uani 1 1 d . . . H14A H -0.2383 0.2751 0.7407 0.067 Uiso 1 1 calc R . . H14B H -0.1928 0.4279 0.6863 0.067 Uiso 1 1 calc R . . H14C H -0.1979 0.5385 0.7499 0.067 Uiso 1 1 calc R . . C15 C 0.1301(3) 0.5419(5) 0.72072(10) 0.0340(6) Uani 1 1 d . . . O16 O 0.0842(2) 0.7417(3) 0.72226(7) 0.0383(4) Uani 1 1 d . . . N17 N 0.2820(3) 0.4815(4) 0.70108(9) 0.0346(5) Uani 1 1 d . . . H17 H 0.320(4) 0.327(6) 0.7027(13) 0.048(9) Uiso 1 1 d . . . C18 C 0.3952(3) 0.6483(5) 0.67744(10) 0.0340(6) Uani 1 1 d . . . H18 H 0.5084 0.5725 0.6742 0.041 Uiso 1 1 calc R . . C19 C 0.4272(3) 0.8492(5) 0.71808(11) 0.0350(6) Uani 1 1 d . . . O20 O 0.4395(2) 1.0421(3) 0.70121(7) 0.0407(5) Uani 1 1 d . . . O21 O 0.4510(2) 0.7881(3) 0.77412(7) 0.0382(5) Uani 1 1 d . . . C22 C 0.4804(4) 0.9747(5) 0.81488(11) 0.0423(7) Uani 1 1 d . . . H22A H 0.5824 1.0590 0.8052 0.063 Uiso 1 1 calc R . . H22B H 0.4979 0.9154 0.8548 0.063 Uiso 1 1 calc R . . H22C H 0.3806 1.0754 0.8121 0.063 Uiso 1 1 calc R . . C23 C 0.3327(3) 0.7272(5) 0.61571(10) 0.0352(6) Uani 1 1 d . . . H23A H 0.2156 0.7895 0.6168 0.042 Uiso 1 1 calc R . . H23B H 0.4081 0.8509 0.6039 0.042 Uiso 1 1 calc R . . C24 C 0.3301(3) 0.5441(5) 0.57026(10) 0.0339(5) Uani 1 1 d . . . C25 C 0.4136(3) 0.3408(5) 0.57250(11) 0.0363(6) Uani 1 1 d . . . H25 H 0.4823 0.2849 0.6053 0.044 Uiso 1 1 calc R . . N26 N 0.3828(3) 0.2288(4) 0.51971(9) 0.0371(5) Uani 1 1 d . . . H26 H 0.433(5) 0.101(7) 0.5117(16) 0.066(11) Uiso 1 1 d . . . C27 C 0.2795(3) 0.3611(5) 0.48241(11) 0.0331(5) Uani 1 1 d . . . C28 C 0.2183(3) 0.3223(5) 0.42434(11) 0.0385(6) Uani 1 1 d . . . H28 H 0.2448 0.1872 0.4045 0.046 Uiso 1 1 calc R . . C29 C 0.1182(3) 0.4884(5) 0.39725(11) 0.0396(6) Uani 1 1 d . . . H29 H 0.0755 0.4676 0.3577 0.048 Uiso 1 1 calc R . . C30 C 0.0772(3) 0.6887(5) 0.42652(11) 0.0389(6) Uani 1 1 d . . . H30 H 0.0066 0.7992 0.4066 0.047 Uiso 1 1 calc R . . C31 C 0.1388(3) 0.7264(5) 0.48408(10) 0.0353(6) Uani 1 1 d . . . H31 H 0.1113 0.8617 0.5036 0.042 Uiso 1 1 calc R . . C32 C 0.2421(3) 0.5618(5) 0.51274(10) 0.0326(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0367(12) 0.0356(15) 0.0301(12) -0.0010(11) 0.0008(10) -0.0013(11) C2 0.0389(12) 0.0392(15) 0.0305(12) 0.0012(11) 0.0022(10) 0.0011(12) C3 0.0350(12) 0.0322(15) 0.0318(12) 0.0007(10) 0.0015(9) -0.0008(11) C4 0.0392(13) 0.0344(15) 0.0350(12) 0.0002(11) 0.0008(10) -0.0028(11) C5 0.0398(13) 0.0370(15) 0.0329(12) -0.0032(11) -0.0001(10) 0.0006(12) C6 0.0351(12) 0.0398(15) 0.0286(12) 0.0024(11) 0.0020(9) 0.0021(12) C7 0.0384(13) 0.0358(15) 0.0309(12) 0.0025(10) 0.0022(10) -0.0007(11) C8 0.0349(12) 0.0350(14) 0.0320(12) -0.0003(11) 0.0012(9) -0.0001(11) C9 0.0415(13) 0.0362(16) 0.0327(12) -0.0006(12) 0.0017(10) -0.0023(12) C10 0.0407(14) 0.0378(16) 0.0343(13) -0.0029(11) 0.0019(10) -0.0039(12) O11 0.0445(10) 0.0422(11) 0.0270(8) 0.0024(8) -0.0008(7) -0.0021(9) C12 0.0506(15) 0.0440(17) 0.0314(12) 0.0045(12) 0.0006(11) 0.0001(13) C13 0.0401(13) 0.0402(15) 0.0287(12) -0.0006(11) 0.0027(10) -0.0032(12) C14 0.0402(14) 0.0583(19) 0.0354(13) 0.0027(13) 0.0002(11) 0.0011(13) C15 0.0393(13) 0.0369(15) 0.0251(11) -0.0019(10) -0.0019(9) 0.0036(12) O16 0.0430(10) 0.0401(11) 0.0316(9) -0.0006(8) 0.0015(7) 0.0047(9) N17 0.0378(11) 0.0370(13) 0.0289(10) 0.0039(9) 0.0027(8) 0.0037(10) C18 0.0380(13) 0.0356(14) 0.0285(11) 0.0027(11) 0.0025(9) -0.0004(11) C19 0.0350(12) 0.0379(15) 0.0317(12) 0.0036(11) -0.0005(10) 0.0007(11) O20 0.0524(11) 0.0367(11) 0.0326(9) 0.0006(8) 0.0002(8) 0.0003(9) O21 0.0460(10) 0.0401(12) 0.0277(8) -0.0007(8) -0.0024(7) -0.0004(8) C22 0.0479(15) 0.0461(17) 0.0317(13) -0.0031(12) -0.0050(11) -0.0010(13) C23 0.0430(13) 0.0343(14) 0.0278(11) 0.0005(11) 0.0005(9) -0.0001(12) C24 0.0359(12) 0.0402(14) 0.0255(11) 0.0009(11) 0.0021(9) -0.0023(12) C25 0.0399(13) 0.0394(15) 0.0294(12) 0.0016(11) 0.0004(10) 0.0002(12) N26 0.0405(11) 0.0371(13) 0.0332(11) -0.0009(10) 0.0002(8) 0.0070(11) C27 0.0363(12) 0.0334(14) 0.0299(11) 0.0005(10) 0.0038(9) 0.0004(11) C28 0.0430(13) 0.0410(16) 0.0316(12) -0.0037(12) 0.0021(10) 0.0009(12) C29 0.0415(13) 0.0451(17) 0.0317(12) 0.0002(12) -0.0007(10) -0.0038(13) C30 0.0410(13) 0.0412(16) 0.0341(12) 0.0045(12) 0.0000(10) -0.0002(12) C31 0.0371(12) 0.0342(14) 0.0347(12) 0.0013(11) 0.0035(10) -0.0010(12) C32 0.0339(12) 0.0349(14) 0.0287(11) 0.0018(10) 0.0006(9) -0.0009(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(4) . ? C1 C10 1.422(4) . ? C1 C13 1.523(3) . ? C2 C3 1.425(3) . ? C2 H2 0.9500 . ? C3 C4 1.419(4) . ? C3 C8 1.422(4) . ? C4 C5 1.368(3) . ? C4 H4 0.9500 . ? C5 C6 1.415(4) . ? C5 H5 0.9500 . ? C6 C7 1.364(4) . ? C6 O11 1.373(3) . ? C7 C8 1.426(3) . ? C7 H7 0.9500 . ? C8 C9 1.422(4) . ? C9 C10 1.367(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O11 C12 1.426(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.526(4) . ? C13 C14 1.526(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O16 1.236(3) . ? C15 N17 1.349(3) . ? N17 C18 1.457(3) . ? N17 H17 0.96(4) . ? C18 C19 1.520(4) . ? C18 C23 1.536(3) . ? C18 H18 1.0000 . ? C19 O20 1.211(3) . ? C19 O21 1.335(3) . ? O21 C22 1.454(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.502(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.368(4) . ? C24 C32 1.446(3) . ? C25 N26 1.385(3) . ? C25 H25 0.9500 . ? N26 C27 1.377(3) . ? N26 H26 0.88(4) . ? C27 C28 1.400(3) . ? C27 C32 1.417(4) . ? C28 C29 1.376(4) . ? C28 H28 0.9500 . ? C29 C30 1.410(4) . ? C29 H29 0.9500 . ? C30 C31 1.389(3) . ? C30 H30 0.9500 . ? C31 C32 1.398(4) . ? C31 H31 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 118.3(2) . . ? C2 C1 C13 123.7(3) . . ? C10 C1 C13 118.0(2) . . ? C1 C2 C3 121.7(3) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C8 118.7(2) . . ? C4 C3 C2 122.0(2) . . ? C8 C3 C2 119.3(2) . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 O11 125.6(2) . . ? C7 C6 C5 120.9(2) . . ? O11 C6 C5 113.5(2) . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C3 118.2(2) . . ? C9 C8 C7 122.2(3) . . ? C3 C8 C7 119.6(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C1 121.8(2) . . ? C9 C10 H10 119.1 . . ? C1 C10 H10 119.1 . . ? C6 O11 C12 117.5(2) . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C13 C15 111.7(2) . . ? C1 C13 C14 111.9(2) . . ? C15 C13 C14 110.0(2) . . ? C1 C13 H13 107.7 . . ? C15 C13 H13 107.7 . . ? C14 C13 H13 107.7 . . ? 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 . . ? O16 C15 N17 121.8(3) . . ? O16 C15 C13 122.7(2) . . ? N17 C15 C13 115.5(2) . . ? C15 N17 C18 121.3(2) . . ? C15 N17 H17 121(2) . . ? C18 N17 H17 118(2) . . ? N17 C18 C19 112.3(2) . . ? N17 C18 C23 112.8(2) . . ? C19 C18 C23 110.7(2) . . ? N17 C18 H18 106.9 . . ? C19 C18 H18 106.9 . . ? C23 C18 H18 106.9 . . ? O20 C19 O21 123.6(2) . . ? O20 C19 C18 123.7(2) . . ? O21 C19 C18 112.5(2) . . ? C19 O21 C22 114.7(2) . . ? O21 C22 H22A 109.5 . . ? O21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C18 114.0(2) . . ? C24 C23 H23A 108.7 . . ? C18 C23 H23A 108.7 . . ? C24 C23 H23B 108.7 . . ? C18 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C25 C24 C32 107.0(2) . . ? C25 C24 C23 128.8(2) . . ? C32 C24 C23 124.2(2) . . ? C24 C25 N26 109.6(2) . . ? C24 C25 H25 125.2 . . ? N26 C25 H25 125.2 . . ? C27 N26 C25 109.1(2) . . ? C27 N26 H26 128(2) . . ? C25 N26 H26 123(2) . . ? N26 C27 C28 129.9(3) . . ? N26 C27 C32 107.7(2) . . ? C28 C27 C32 122.4(2) . . ? C29 C28 C27 117.1(3) . . ? C29 C28 H28 121.4 . . ? C27 C28 H28 121.4 . . ? C28 C29 C30 121.8(2) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 118.9(3) . . ? C30 C31 H31 120.6 . . ? C32 C31 H31 120.6 . . ? C31 C32 C27 119.1(2) . . ? C31 C32 C24 134.3(2) . . ? C27 C32 C24 106.6(2) . . ? 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 C10 C1 C2 C3 0.3(4) . . . . ? C13 C1 C2 C3 -179.3(2) . . . . ? C1 C2 C3 C4 179.0(3) . . . . ? C1 C2 C3 C8 -0.8(4) . . . . ? C8 C3 C4 C5 0.9(4) . . . . ? C2 C3 C4 C5 -178.9(2) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C4 C5 C6 O11 179.7(2) . . . . ? O11 C6 C7 C8 -179.0(2) . . . . ? C5 C6 C7 C8 1.2(4) . . . . ? C4 C3 C8 C9 -179.3(2) . . . . ? C2 C3 C8 C9 0.5(4) . . . . ? C4 C3 C8 C7 -0.1(4) . . . . ? C2 C3 C8 C7 179.7(2) . . . . ? C6 C7 C8 C9 178.2(3) . . . . ? C6 C7 C8 C3 -0.9(4) . . . . ? C3 C8 C9 C10 0.2(4) . . . . ? C7 C8 C9 C10 -178.9(2) . . . . ? C8 C9 C10 C1 -0.7(4) . . . . ? C2 C1 C10 C9 0.5(4) . . . . ? C13 C1 C10 C9 -179.9(2) . . . . ? C7 C6 O11 C12 6.3(4) . . . . ? C5 C6 O11 C12 -173.8(2) . . . . ? C2 C1 C13 C15 14.2(4) . . . . ? C10 C1 C13 C15 -165.5(2) . . . . ? C2 C1 C13 C14 -109.6(3) . . . . ? C10 C1 C13 C14 70.7(3) . . . . ? C1 C13 C15 O16 -91.4(3) . . . . ? C14 C13 C15 O16 33.4(3) . . . . ? C1 C13 C15 N17 88.0(3) . . . . ? C14 C13 C15 N17 -147.1(2) . . . . ? O16 C15 N17 C18 -3.7(3) . . . . ? C13 C15 N17 C18 176.86(19) . . . . ? C15 N17 C18 C19 50.8(3) . . . . ? C15 N17 C18 C23 -75.1(3) . . . . ? N17 C18 C19 O20 -142.6(3) . . . . ? C23 C18 C19 O20 -15.5(3) . . . . ? N17 C18 C19 O21 41.4(3) . . . . ? C23 C18 C19 O21 168.5(2) . . . . ? O20 C19 O21 C22 4.6(4) . . . . ? C18 C19 O21 C22 -179.4(2) . . . . ? N17 C18 C23 C24 -64.2(3) . . . . ? C19 C18 C23 C24 169.0(2) . . . . ? C18 C23 C24 C25 -18.5(4) . . . . ? C18 C23 C24 C32 165.6(2) . . . . ? C32 C24 C25 N26 -0.2(3) . . . . ? C23 C24 C25 N26 -176.7(3) . . . . ? C24 C25 N26 C27 0.6(3) . . . . ? C25 N26 C27 C28 178.1(3) . . . . ? C25 N26 C27 C32 -0.7(3) . . . . ? N26 C27 C28 C29 -179.0(3) . . . . ? C32 C27 C28 C29 -0.3(4) . . . . ? C27 C28 C29 C30 -0.5(4) . . . . ? C28 C29 C30 C31 0.7(4) . . . . ? C29 C30 C31 C32 -0.2(4) . . . . ? C30 C31 C32 C27 -0.5(4) . . . . ? C30 C31 C32 C24 178.3(3) . . . . ? N26 C27 C32 C31 179.7(2) . . . . ? C28 C27 C32 C31 0.8(4) . . . . ? N26 C27 C32 C24 0.6(3) . . . . ? C28 C27 C32 C24 -178.4(2) . . . . ? C25 C24 C32 C31 -179.2(3) . . . . ? C23 C24 C32 C31 -2.5(5) . . . . ? C25 C24 C32 C27 -0.2(3) . . . . ? C23 C24 C32 C27 176.5(2) . . . . ? 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 N17 H17 O20 0.96(4) 1.93(4) 2.876(3) 168(3) 1_545 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 68.65 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.179 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 662958' ####################################################################### # # 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_2004uv04 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 N O5' _chemical_formula_weight 407.45 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.6471(2) _cell_length_b 8.0554(4) _cell_length_c 45.153(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2054.01(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.753 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6607 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 72.11 _reflns_number_total 3911 _reflns_number_gt 3672 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0429P)^2^+0.3755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0042(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(17) _refine_ls_number_reflns 3911 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C1 C 0.6963(3) 0.84755(19) 0.09723(3) 0.0289(3) Uani 1 1 d . . . C2 C 0.8366(3) 0.9410(2) 0.07906(4) 0.0299(3) Uani 1 1 d . . . H2 H 0.984(4) 0.986(2) 0.0873(4) 0.038(5) Uiso 1 1 d . . . C3 C 0.7767(3) 0.97039(19) 0.04893(4) 0.0283(3) Uani 1 1 d . . . C4 C 0.9192(3) 1.06776(19) 0.02976(4) 0.0309(3) Uani 1 1 d . . . H4 H 1.076(4) 1.120(2) 0.0380(4) 0.037(5) Uiso 1 1 d . . . C5 C 0.8546(3) 1.0938(2) 0.00095(3) 0.0303(3) Uani 1 1 d . . . H5 H 0.947(3) 1.162(2) -0.0127(4) 0.034(5) Uiso 1 1 d . . . C6 C 0.6460(3) 1.02119(19) -0.01049(3) 0.0285(3) Uani 1 1 d . . . C7 C 0.5034(3) 0.9249(2) 0.00708(3) 0.0287(3) Uani 1 1 d . . . H7 H 0.359(3) 0.871(2) -0.0007(4) 0.028(4) Uiso 1 1 d . . . C8 C 0.5652(3) 0.8994(2) 0.03732(3) 0.0279(3) Uani 1 1 d . . . C9 C 0.4209(3) 0.8045(2) 0.05660(3) 0.0297(3) Uani 1 1 d . . . H9 H 0.269(3) 0.760(2) 0.0492(4) 0.031(5) Uiso 1 1 d . . . C10 C 0.4835(3) 0.7807(2) 0.08561(4) 0.0301(3) Uani 1 1 d . . . H10 H 0.382(3) 0.714(2) 0.0991(4) 0.026(4) Uiso 1 1 d . . . O11 O 0.6043(2) 1.05695(14) -0.03975(2) 0.0308(3) Uani 1 1 d . . . C12 C 0.3851(3) 1.0008(2) -0.05186(4) 0.0344(4) Uani 1 1 d . . . H12A H 0.253(4) 1.040(3) -0.0398(5) 0.045(6) Uiso 1 1 d . . . H12B H 0.380(4) 0.881(3) -0.0535(5) 0.048(6) Uiso 1 1 d . . . H12C H 0.377(4) 1.045(3) -0.0731(5) 0.043(5) Uiso 1 1 d . . . C13 C 0.7656(3) 0.8150(2) 0.12944(4) 0.0305(4) Uani 1 1 d . . . H13 H 0.912(4) 0.867(3) 0.1327(5) 0.044(6) Uiso 1 1 d . . . C14 C 0.7821(4) 0.6288(2) 0.13646(4) 0.0431(5) Uani 1 1 d . . . H14A H 0.830(4) 0.613(3) 0.1579(5) 0.045(5) Uiso 1 1 d . . . H14B H 0.618(5) 0.577(3) 0.1323(5) 0.058(6) Uiso 1 1 d . . . H14C H 0.923(5) 0.577(3) 0.1234(5) 0.061(7) Uiso 1 1 d . . . C15 C 0.5817(3) 0.8979(2) 0.14873(3) 0.0301(3) Uani 1 1 d . . . O16 O 0.3776(2) 0.84172(16) 0.15102(2) 0.0390(3) Uani 1 1 d . . . N17 N 0.6436(3) 1.04122(17) 0.16193(3) 0.0302(3) Uani 1 1 d . . . H17 H 0.796(4) 1.090(3) 0.1575(5) 0.048(6) Uiso 1 1 d . . . C18 C 0.4594(3) 1.1537(2) 0.17248(4) 0.0313(3) Uani 1 1 d . . . H18 H 0.354(3) 1.092(2) 0.1863(4) 0.031(4) Uiso 1 1 d . . . C19 C 0.3085(3) 1.2096(2) 0.14637(4) 0.0318(4) Uani 1 1 d . . . O20 O 0.0958(2) 1.22350(17) 0.14661(3) 0.0426(3) Uani 1 1 d . . . O21 O 0.4439(2) 1.24549(15) 0.12300(2) 0.0366(3) Uani 1 1 d . . . C22 C 0.3286(4) 1.2979(3) 0.09618(4) 0.0448(5) Uani 1 1 d . . . H22A H 0.163(6) 1.256(4) 0.0950(6) 0.089(9) Uiso 1 1 d . . . H22B H 0.404(8) 1.226(5) 0.0785(9) 0.132(14) Uiso 1 1 d . . . H22C H 0.315(7) 1.400(5) 0.0949(7) 0.105(12) Uiso 1 1 d . . . C23 C 0.5683(3) 1.3057(2) 0.18819(4) 0.0321(4) Uani 1 1 d . . . H23A H 0.702(4) 1.350(2) 0.1750(4) 0.035(5) Uiso 1 1 d . . . H23B H 0.445(4) 1.397(3) 0.1889(4) 0.040(5) Uiso 1 1 d . . . C24 C 0.6500(3) 1.2700(2) 0.21937(3) 0.0302(3) Uani 1 1 d . . . C25 C 0.5145(3) 1.3205(2) 0.24331(4) 0.0322(4) Uani 1 1 d . . . H25 H 0.354(4) 1.385(2) 0.2403(4) 0.039(5) Uiso 1 1 d . . . C26 C 0.5857(3) 1.2910(2) 0.27217(4) 0.0336(4) Uani 1 1 d . . . H26 H 0.488(4) 1.328(2) 0.2883(5) 0.040(5) Uiso 1 1 d . . . C27 C 0.7977(3) 1.2102(2) 0.27767(3) 0.0334(4) Uani 1 1 d . . . C28 C 0.9367(3) 1.1564(2) 0.25404(4) 0.0348(4) Uani 1 1 d . . . H28 H 1.085(4) 1.094(3) 0.2577(4) 0.044(5) Uiso 1 1 d . . . C29 C 0.8632(3) 1.1877(2) 0.22532(4) 0.0343(4) Uani 1 1 d . . . H29 H 0.962(4) 1.145(2) 0.2099(5) 0.041(5) Uiso 1 1 d . . . O30 O 0.8769(2) 1.17668(18) 0.30570(3) 0.0445(3) Uani 1 1 d . . . H30 H 0.781(5) 1.233(3) 0.3196(6) 0.075(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0319(8) 0.0287(8) 0.0261(8) -0.0026(6) -0.0013(6) 0.0023(7) C2 0.0293(8) 0.0295(8) 0.0309(8) -0.0051(6) -0.0032(7) -0.0001(6) C3 0.0297(8) 0.0250(8) 0.0302(8) -0.0028(6) 0.0005(6) 0.0017(6) C4 0.0289(8) 0.0296(8) 0.0341(8) -0.0027(6) -0.0006(7) -0.0007(7) C5 0.0325(8) 0.0277(8) 0.0307(8) 0.0003(6) 0.0037(7) 0.0000(7) C6 0.0313(8) 0.0274(8) 0.0267(7) -0.0012(6) 0.0015(6) 0.0035(6) C7 0.0289(8) 0.0289(8) 0.0282(8) -0.0018(6) -0.0014(6) 0.0005(6) C8 0.0284(8) 0.0272(7) 0.0281(7) -0.0028(6) 0.0003(6) 0.0018(6) C9 0.0284(8) 0.0310(8) 0.0295(8) -0.0008(6) -0.0016(6) -0.0022(6) C10 0.0319(8) 0.0306(8) 0.0277(8) 0.0000(6) 0.0010(6) -0.0017(7) O11 0.0339(6) 0.0328(6) 0.0258(5) 0.0010(4) -0.0001(5) -0.0017(5) C12 0.0350(9) 0.0389(10) 0.0295(8) 0.0000(7) -0.0004(7) -0.0007(7) C13 0.0336(9) 0.0305(8) 0.0275(8) -0.0008(6) -0.0044(6) -0.0020(7) C14 0.0586(12) 0.0343(10) 0.0365(10) 0.0026(8) -0.0151(9) 0.0023(9) C15 0.0343(8) 0.0336(8) 0.0225(7) 0.0041(6) -0.0032(6) -0.0046(7) O16 0.0386(7) 0.0494(7) 0.0289(6) -0.0019(5) 0.0025(5) -0.0132(6) N17 0.0300(7) 0.0332(7) 0.0273(6) -0.0003(5) -0.0001(6) -0.0014(6) C18 0.0301(8) 0.0381(9) 0.0257(7) 0.0005(7) 0.0022(6) 0.0003(7) C19 0.0309(8) 0.0340(8) 0.0306(8) 0.0001(7) 0.0007(7) -0.0022(7) O20 0.0299(6) 0.0548(8) 0.0431(7) 0.0057(6) -0.0011(5) 0.0000(6) O21 0.0337(6) 0.0505(7) 0.0257(6) 0.0064(5) -0.0019(5) -0.0017(5) C22 0.0497(12) 0.0514(12) 0.0331(9) 0.0111(8) -0.0117(8) -0.0050(9) C23 0.0362(8) 0.0333(9) 0.0269(7) -0.0008(7) 0.0004(7) 0.0013(7) C24 0.0325(8) 0.0313(8) 0.0269(8) -0.0024(6) 0.0002(7) -0.0026(7) C25 0.0320(8) 0.0323(9) 0.0322(8) -0.0034(7) 0.0000(7) 0.0016(7) C26 0.0356(9) 0.0371(9) 0.0282(8) -0.0043(7) 0.0013(7) 0.0032(7) C27 0.0356(9) 0.0384(9) 0.0261(8) -0.0007(7) -0.0036(7) -0.0012(7) C28 0.0316(9) 0.0404(9) 0.0324(8) -0.0018(7) -0.0008(7) 0.0026(7) C29 0.0312(8) 0.0396(9) 0.0320(8) -0.0019(7) 0.0036(7) 0.0013(7) O30 0.0440(7) 0.0633(8) 0.0262(6) -0.0026(6) -0.0038(5) 0.0136(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.367(2) . ? C1 C10 1.418(2) . ? C1 C13 1.529(2) . ? C2 C3 1.422(2) . ? C2 H2 0.98(2) . ? C3 C4 1.418(2) . ? C3 C8 1.424(2) . ? C4 C5 1.367(2) . ? C4 H4 1.05(2) . ? C5 C6 1.413(2) . ? C5 H5 0.97(2) . ? C6 C7 1.371(2) . ? C6 O11 1.3726(18) . ? C7 C8 1.424(2) . ? C7 H7 0.990(19) . ? C8 C9 1.417(2) . ? C9 C10 1.370(2) . ? C9 H9 0.987(19) . ? C10 H10 0.993(19) . ? O11 C12 1.427(2) . ? C12 H12A 0.97(2) . ? C12 H12B 0.97(2) . ? C12 H12C 1.02(2) . ? C13 C15 1.511(2) . ? C13 C14 1.535(3) . ? C13 H13 0.94(2) . ? C14 H14A 1.01(2) . ? C14 H14B 1.03(3) . ? C14 H14C 1.08(3) . ? C15 O16 1.242(2) . ? C15 N17 1.345(2) . ? N17 C18 1.460(2) . ? N17 H17 0.97(2) . ? C18 C19 1.523(2) . ? C18 C23 1.543(2) . ? C18 H18 0.994(19) . ? C19 O20 1.206(2) . ? C19 O21 1.335(2) . ? O21 C22 1.438(2) . ? C22 H22A 1.00(4) . ? C22 H22B 1.08(4) . ? C22 H22C 0.83(4) . ? C23 C24 1.509(2) . ? C23 H23A 1.03(2) . ? C23 H23B 1.01(2) . ? C24 C25 1.385(2) . ? C24 C29 1.401(2) . ? C25 C26 1.384(2) . ? C25 H25 1.05(2) . ? C26 C27 1.386(2) . ? C26 H26 0.96(2) . ? C27 O30 1.3691(19) . ? C27 C28 1.394(2) . ? C28 C29 1.385(2) . ? C28 H28 0.99(2) . ? C29 H29 0.95(2) . ? O30 H30 0.94(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 C2 C1 C10 118.60(14) . . ? C2 C1 C13 121.16(14) . . ? C10 C1 C13 120.24(14) . . ? C1 C2 C3 121.88(15) . . ? C1 C2 H2 117.9(12) . . ? C3 C2 H2 120.2(12) . . ? C4 C3 C2 122.75(15) . . ? C4 C3 C8 118.24(15) . . ? C2 C3 C8 119.01(15) . . ? C5 C4 C3 120.94(15) . . ? C5 C4 H4 120.1(11) . . ? C3 C4 H4 119.0(11) . . ? C4 C5 C6 120.45(15) . . ? C4 C5 H5 123.0(11) . . ? C6 C5 H5 116.6(11) . . ? C7 C6 O11 125.10(15) . . ? C7 C6 C5 120.81(15) . . ? O11 C6 C5 114.09(14) . . ? C6 C7 C8 119.51(15) . . ? C6 C7 H7 121.7(10) . . ? C8 C7 H7 118.8(10) . . ? C9 C8 C3 118.26(14) . . ? C9 C8 C7 121.72(15) . . ? C3 C8 C7 120.02(15) . . ? C10 C9 C8 120.94(15) . . ? C10 C9 H9 119.9(11) . . ? C8 C9 H9 119.1(11) . . ? C9 C10 C1 121.29(15) . . ? C9 C10 H10 120.8(10) . . ? C1 C10 H10 117.9(10) . . ? C6 O11 C12 116.82(12) . . ? O11 C12 H12A 110.2(13) . . ? O11 C12 H12B 111.8(14) . . ? H12A C12 H12B 109.7(19) . . ? O11 C12 H12C 106.8(12) . . ? H12A C12 H12C 112.0(17) . . ? H12B C12 H12C 106.2(17) . . ? C15 C13 C1 107.26(13) . . ? C15 C13 C14 110.77(15) . . ? C1 C13 C14 112.31(14) . . ? C15 C13 H13 108.7(13) . . ? C1 C13 H13 107.4(13) . . ? C14 C13 H13 110.3(13) . . ? C13 C14 H14A 109.8(12) . . ? C13 C14 H14B 107.7(14) . . ? H14A C14 H14B 111.0(19) . . ? C13 C14 H14C 108.1(13) . . ? H14A C14 H14C 106.1(19) . . ? H14B C14 H14C 114.1(18) . . ? O16 C15 N17 121.14(16) . . ? O16 C15 C13 121.60(15) . . ? N17 C15 C13 117.14(14) . . ? C15 N17 C18 119.46(14) . . ? C15 N17 H17 119.1(13) . . ? C18 N17 H17 116.9(13) . . ? N17 C18 C19 109.27(13) . . ? N17 C18 C23 111.01(14) . . ? C19 C18 C23 110.15(14) . . ? N17 C18 H18 108.8(11) . . ? C19 C18 H18 107.4(11) . . ? C23 C18 H18 110.1(10) . . ? O20 C19 O21 123.88(16) . . ? O20 C19 C18 125.27(15) . . ? O21 C19 C18 110.84(13) . . ? C19 O21 C22 118.04(14) . . ? O21 C22 H22A 111.8(17) . . ? O21 C22 H22B 107(2) . . ? H22A C22 H22B 98(3) . . ? O21 C22 H22C 113(2) . . ? H22A C22 H22C 104(3) . . ? H22B C22 H22C 121(3) . . ? C24 C23 C18 113.57(14) . . ? C24 C23 H23A 112.4(11) . . ? C18 C23 H23A 107.7(11) . . ? C24 C23 H23B 108.6(11) . . ? C18 C23 H23B 108.3(12) . . ? H23A C23 H23B 105.9(16) . . ? C25 C24 C29 117.64(15) . . ? C25 C24 C23 120.23(15) . . ? C29 C24 C23 122.13(15) . . ? C26 C25 C24 121.61(16) . . ? C26 C25 H25 117.0(10) . . ? C24 C25 H25 121.3(11) . . ? C25 C26 C27 120.01(16) . . ? C25 C26 H26 119.6(13) . . ? C27 C26 H26 120.4(13) . . ? O30 C27 C26 122.71(15) . . ? O30 C27 C28 117.57(16) . . ? C26 C27 C28 119.71(15) . . ? C29 C28 C27 119.46(16) . . ? C29 C28 H28 120.1(12) . . ? C27 C28 H28 120.4(12) . . ? C28 C29 C24 121.56(16) . . ? C28 C29 H29 116.4(13) . . ? C24 C29 H29 121.9(13) . . ? C27 O30 H30 109.4(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -1.0(2) . . . . ? C13 C1 C2 C3 179.01(15) . . . . ? C1 C2 C3 C4 179.64(15) . . . . ? C1 C2 C3 C8 -0.4(2) . . . . ? C2 C3 C4 C5 -179.64(15) . . . . ? C8 C3 C4 C5 0.4(2) . . . . ? C3 C4 C5 C6 -1.2(2) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C4 C5 C6 O11 -179.56(14) . . . . ? O11 C6 C7 C8 -179.07(14) . . . . ? C5 C6 C7 C8 0.7(2) . . . . ? C4 C3 C8 C9 -178.96(15) . . . . ? C2 C3 C8 C9 1.1(2) . . . . ? C4 C3 C8 C7 0.9(2) . . . . ? C2 C3 C8 C7 -179.02(15) . . . . ? C6 C7 C8 C9 178.40(15) . . . . ? C6 C7 C8 C3 -1.5(2) . . . . ? C3 C8 C9 C10 -0.3(2) . . . . ? C7 C8 C9 C10 179.79(15) . . . . ? C8 C9 C10 C1 -1.1(2) . . . . ? C2 C1 C10 C9 1.8(2) . . . . ? C13 C1 C10 C9 -178.21(15) . . . . ? C7 C6 O11 C12 5.6(2) . . . . ? C5 C6 O11 C12 -174.13(14) . . . . ? C2 C1 C13 C15 115.14(16) . . . . ? C10 C1 C13 C15 -64.83(18) . . . . ? C2 C1 C13 C14 -122.94(18) . . . . ? C10 C1 C13 C14 57.1(2) . . . . ? C1 C13 C15 O16 72.03(19) . . . . ? C14 C13 C15 O16 -50.9(2) . . . . ? C1 C13 C15 N17 -103.99(16) . . . . ? C14 C13 C15 N17 133.12(15) . . . . ? O16 C15 N17 C18 -16.1(2) . . . . ? C13 C15 N17 C18 159.99(14) . . . . ? C15 N17 C18 C19 -61.10(18) . . . . ? C15 N17 C18 C23 177.22(13) . . . . ? N17 C18 C19 O20 138.76(18) . . . . ? C23 C18 C19 O20 -99.0(2) . . . . ? N17 C18 C19 O21 -42.63(18) . . . . ? C23 C18 C19 O21 79.57(17) . . . . ? O20 C19 O21 C22 -2.4(3) . . . . ? C18 C19 O21 C22 179.00(16) . . . . ? N17 C18 C23 C24 -78.19(17) . . . . ? C19 C18 C23 C24 160.65(14) . . . . ? C18 C23 C24 C25 -102.40(18) . . . . ? C18 C23 C24 C29 78.3(2) . . . . ? C29 C24 C25 C26 0.0(3) . . . . ? C23 C24 C25 C26 -179.38(16) . . . . ? C24 C25 C26 C27 0.4(3) . . . . ? C25 C26 C27 O30 -179.60(17) . . . . ? C25 C26 C27 C28 -1.0(3) . . . . ? O30 C27 C28 C29 179.98(16) . . . . ? C26 C27 C28 C29 1.4(3) . . . . ? C27 C28 C29 C24 -1.0(3) . . . . ? C25 C24 C29 C28 0.4(3) . . . . ? C23 C24 C29 C28 179.69(16) . . . . ? 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 N17 H17 O20 0.97(2) 2.07(2) 3.026(2) 172(2) 1_655 O30 H30 O16 0.94(3) 1.83(3) 2.7661(18) 174(3) 4_655 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 72.11 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.211 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 662959' ####################################################################### # # 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_2004uv05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N O6' _chemical_formula_weight 425.47 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.9526(3) _cell_length_b 10.2028(6) _cell_length_c 10.7011(7) _cell_angle_alpha 92.352(4) _cell_angle_beta 94.615(4) _cell_angle_gamma 96.777(4) _cell_volume 534.51(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 226 _exptl_absorpt_coefficient_mu 0.781 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8111 _exptl_absorpt_correction_T_max 0.9620 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3369 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 68.33 _reflns_number_total 3369 _reflns_number_gt 3086 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0912P)^2^+0.2886P] 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(3) _refine_ls_number_reflns 3369 _refine_ls_number_parameters 333 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1619 _refine_ls_wR_factor_gt 0.1505 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.122 _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 C1 C 0.3264(7) 0.7713(3) 0.5986(4) 0.0306(8) Uani 1 1 d . . . C2 C 0.3571(7) 0.7455(3) 0.4741(4) 0.0324(8) Uani 1 1 d . . . H2 H 0.4777 0.6840 0.4525 0.039 Uiso 1 1 calc R . . C3 C 0.2167(7) 0.8066(3) 0.3769(4) 0.0303(8) Uani 1 1 d . . . C4 C 0.2437(8) 0.7792(3) 0.2484(4) 0.0342(8) Uani 1 1 d . . . H4 H 0.3625 0.7176 0.2251 0.041 Uiso 1 1 calc R . . C5 C 0.1030(7) 0.8394(3) 0.1573(4) 0.0344(8) Uani 1 1 d . . . H5 H 0.1223 0.8184 0.0715 0.041 Uiso 1 1 calc R . . C6 C -0.0738(7) 0.9341(3) 0.1902(4) 0.0342(8) Uani 1 1 d . . . C7 C -0.1067(7) 0.9624(3) 0.3134(4) 0.0318(8) Uani 1 1 d . . . H7 H -0.2260 1.0246 0.3349 0.038 Uiso 1 1 calc R . . C8 C 0.0372(7) 0.8992(3) 0.4101(4) 0.0320(8) Uani 1 1 d . . . C9 C 0.0078(8) 0.9256(3) 0.5376(4) 0.0328(8) Uani 1 1 d . . . H9 H -0.1104 0.9876 0.5608 0.039 Uiso 1 1 calc R . . C10 C 0.1466(7) 0.8636(3) 0.6295(4) 0.0352(8) Uani 1 1 d . . . H10 H 0.1217 0.8828 0.7151 0.042 Uiso 1 1 calc R . . O11 O -0.1934(5) 0.9915(3) 0.0909(3) 0.0398(6) Uani 1 1 d . . . C12 C -0.3499(8) 1.0962(4) 0.1215(4) 0.0374(8) Uani 1 1 d . . . H12A H -0.394(8) 1.129(4) 0.031(4) 0.031(10) Uiso 1 1 d . . . H12B H -0.223(10) 1.168(5) 0.178(5) 0.048(12) Uiso 1 1 d . . . H12C H -0.508(9) 1.066(4) 0.169(4) 0.028(9) Uiso 1 1 d . . . C13 C 0.4711(7) 0.6970(3) 0.6994(4) 0.0329(8) Uani 1 1 d . . . H13 H 0.6653 0.6970 0.6801 0.039 Uiso 1 1 calc R . . C14 C 0.4698(9) 0.7523(4) 0.8337(4) 0.0413(9) Uani 1 1 d . . . H14A H 0.578(10) 0.709(5) 0.892(5) 0.046(12) Uiso 1 1 d . . . H14B H 0.273(9) 0.739(4) 0.858(4) 0.031(10) Uiso 1 1 d . . . H14C H 0.550(11) 0.854(5) 0.845(5) 0.057(14) Uiso 1 1 d . . . C15 C 0.3351(6) 0.5552(3) 0.6885(3) 0.0276(7) Uani 1 1 d . . . O16 O 0.0896(5) 0.5266(2) 0.7050(3) 0.0332(6) Uani 1 1 d . . . N17 N 0.4911(6) 0.4625(3) 0.6566(3) 0.0301(7) Uani 1 1 d . . . H17 H 0.665(12) 0.480(5) 0.653(5) 0.054(14) Uiso 1 1 d . . . C18 C 0.3785(7) 0.3252(3) 0.6335(4) 0.0289(7) Uani 1 1 d . . . H18 H 0.1917 0.3233 0.5899 0.035 Uiso 1 1 calc R . . C19 C 0.3488(7) 0.2592(3) 0.7569(3) 0.0296(7) Uani 1 1 d . . . O20 O 0.5131(6) 0.2749(3) 0.8457(3) 0.0472(7) Uani 1 1 d . . . O21 O 0.1141(5) 0.1789(2) 0.7526(2) 0.0334(6) Uani 1 1 d . . . C22 C 0.0575(9) 0.1153(4) 0.8673(4) 0.0378(9) Uani 1 1 d . . . H22A H -0.130(11) 0.063(5) 0.846(5) 0.052(13) Uiso 1 1 d . . . H22B H 0.078(10) 0.181(5) 0.936(5) 0.050(13) Uiso 1 1 d . . . H22C H 0.200(11) 0.056(5) 0.893(5) 0.052(13) Uiso 1 1 d . . . C23 C 0.5498(7) 0.2547(3) 0.5462(4) 0.0306(7) Uani 1 1 d . . . H23A H 0.7386 0.2587 0.5856 0.037 Uiso 1 1 calc R . . H23B H 0.4733 0.1606 0.5335 0.037 Uiso 1 1 calc R . . C24 C 0.5548(7) 0.3170(3) 0.4207(4) 0.0295(7) Uani 1 1 d . . . C25 C 0.3388(7) 0.2828(3) 0.3276(4) 0.0332(8) Uani 1 1 d . . . H25 H 0.1980 0.2149 0.3420 0.040 Uiso 1 1 calc R . . C26 C 0.3256(7) 0.3448(3) 0.2165(4) 0.0336(8) Uani 1 1 d . . . H26 H 0.1775 0.3192 0.1550 0.040 Uiso 1 1 calc R . . C27 C 0.5287(7) 0.4452(3) 0.1935(4) 0.0300(8) Uani 1 1 d . . . C28 C 0.7436(7) 0.4812(3) 0.2841(4) 0.0330(8) Uani 1 1 d . . . H28 H 0.8831 0.5498 0.2696 0.040 Uiso 1 1 calc R . . C29 C 0.7551(7) 0.4176(4) 0.3949(4) 0.0325(8) Uani 1 1 d . . . H29 H 0.9044 0.4431 0.4558 0.039 Uiso 1 1 calc R . . O30 O 0.5256(5) 0.5103(2) 0.0844(3) 0.0357(6) Uani 1 1 d . . . H30 H 0.361(13) 0.502(6) 0.041(6) 0.069(18) Uiso 1 1 d . . . O1W O 0.0251(6) 0.4805(4) 0.9653(3) 0.0574(9) Uani 1 1 d D . . H1WA H -0.119(10) 0.477(6) 0.997(6) 0.074(19) Uiso 1 1 d D . . H1WB H 0.00(2) 0.490(9) 0.888(5) 0.12(3) 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 C1 0.0289(17) 0.0275(16) 0.035(2) 0.0047(14) 0.0008(14) 0.0005(13) C2 0.0346(18) 0.0265(15) 0.036(2) -0.0005(14) 0.0092(16) 0.0023(13) C3 0.0297(17) 0.0248(15) 0.037(2) 0.0042(14) 0.0089(15) -0.0002(12) C4 0.0399(19) 0.0288(16) 0.035(2) 0.0002(15) 0.0124(16) 0.0044(14) C5 0.0402(19) 0.0349(17) 0.028(2) 0.0019(15) 0.0092(16) 0.0014(14) C6 0.0353(19) 0.0262(16) 0.040(2) 0.0100(15) 0.0064(17) -0.0038(14) C7 0.0364(19) 0.0282(16) 0.031(2) 0.0053(14) 0.0061(16) 0.0024(14) C8 0.0288(16) 0.0246(15) 0.042(2) 0.0013(14) 0.0081(15) -0.0012(12) C9 0.0382(18) 0.0294(16) 0.031(2) -0.0012(14) 0.0028(16) 0.0072(14) C10 0.0356(19) 0.0329(18) 0.038(2) 0.0003(16) 0.0082(16) 0.0040(14) O11 0.0440(15) 0.0389(13) 0.0379(16) 0.0063(12) 0.0062(12) 0.0075(11) C12 0.0336(19) 0.0390(18) 0.040(2) 0.0082(17) 0.0059(17) 0.0040(15) C13 0.0329(18) 0.0295(17) 0.035(2) 0.0010(15) 0.0023(15) 0.0012(13) C14 0.053(2) 0.0363(19) 0.032(2) -0.0013(16) -0.0079(19) 0.0040(17) C15 0.0270(17) 0.0307(16) 0.0252(18) 0.0027(13) 0.0023(13) 0.0035(12) O16 0.0264(12) 0.0350(11) 0.0383(15) 0.0036(10) 0.0052(10) 0.0024(9) N17 0.0255(15) 0.0291(14) 0.0360(18) 0.0005(12) 0.0061(12) 0.0025(11) C18 0.0265(16) 0.0261(15) 0.034(2) 0.0049(14) 0.0046(14) 0.0022(12) C19 0.0308(17) 0.0305(16) 0.028(2) 0.0013(14) 0.0068(15) 0.0038(12) O20 0.0424(15) 0.0600(17) 0.0357(17) 0.0148(14) -0.0038(13) -0.0072(13) O21 0.0352(12) 0.0335(12) 0.0301(14) 0.0066(10) 0.0053(10) -0.0046(9) C22 0.045(2) 0.0358(19) 0.033(2) 0.0078(17) 0.0087(17) -0.0010(17) C23 0.0290(16) 0.0313(17) 0.033(2) 0.0022(15) 0.0075(14) 0.0045(13) C24 0.0288(16) 0.0280(15) 0.032(2) 0.0013(13) 0.0065(14) 0.0047(12) C25 0.0307(18) 0.0308(16) 0.037(2) 0.0006(14) 0.0058(15) -0.0017(13) C26 0.0331(17) 0.0371(18) 0.029(2) -0.0002(15) 0.0031(15) -0.0001(14) C27 0.0274(17) 0.0312(16) 0.033(2) 0.0024(15) 0.0085(14) 0.0048(13) C28 0.0268(17) 0.0342(17) 0.038(2) 0.0028(15) 0.0052(15) -0.0004(13) C29 0.0241(16) 0.0399(18) 0.033(2) 0.0015(15) 0.0036(14) 0.0026(13) O30 0.0363(14) 0.0411(13) 0.0298(15) 0.0075(11) 0.0038(12) 0.0032(11) O1W 0.0347(15) 0.102(3) 0.0355(19) 0.0093(18) 0.0054(14) 0.0049(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(5) . ? C1 C10 1.417(5) . ? C1 C13 1.524(5) . ? C2 C3 1.413(5) . ? C2 H2 0.9500 . ? C3 C4 1.411(5) . ? C3 C8 1.425(4) . ? C4 C5 1.362(6) . ? C4 H4 0.9500 . ? C5 C6 1.430(5) . ? C5 H5 0.9500 . ? C6 O11 1.362(5) . ? C6 C7 1.365(5) . ? C7 C8 1.429(5) . ? C7 H7 0.9500 . ? C8 C9 1.402(5) . ? C9 C10 1.373(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O11 C12 1.434(5) . ? C12 H12A 1.05(4) . ? C12 H12B 1.05(5) . ? C12 H12C 0.99(4) . ? C13 C15 1.519(5) . ? C13 C14 1.523(6) . ? C13 H13 1.0000 . ? C14 H14A 0.94(5) . ? C14 H14B 1.03(4) . ? C14 H14C 1.07(5) . ? C15 O16 1.245(4) . ? C15 N17 1.340(4) . ? N17 C18 1.448(4) . ? N17 H17 0.86(6) . ? C18 C19 1.517(5) . ? C18 C23 1.526(5) . ? C18 H18 1.0000 . ? C19 O20 1.193(5) . ? C19 O21 1.337(4) . ? O21 C22 1.444(4) . ? C22 H22A 1.02(5) . ? C22 H22B 0.97(6) . ? C22 H22C 1.01(5) . ? C23 C24 1.510(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C29 1.393(5) . ? C24 C25 1.404(5) . ? C25 C26 1.370(5) . ? C25 H25 0.9500 . ? C26 C27 1.392(5) . ? C26 H26 0.9500 . ? C27 O30 1.367(4) . ? C27 C28 1.386(5) . ? C28 C29 1.375(6) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? O30 H30 0.90(7) . ? O1W H1WA 0.81(4) . ? O1W H1WB 0.84(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 C2 C1 C10 118.0(3) . . ? C2 C1 C13 120.4(3) . . ? C10 C1 C13 121.5(4) . . ? C1 C2 C3 122.6(3) . . ? C1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 123.1(3) . . ? C4 C3 C8 118.5(3) . . ? C2 C3 C8 118.4(3) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? O11 C6 C7 125.3(3) . . ? O11 C6 C5 114.7(3) . . ? C7 C6 C5 120.0(3) . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C3 118.7(3) . . ? C9 C8 C7 121.9(3) . . ? C3 C8 C7 119.4(3) . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C1 121.0(4) . . ? C9 C10 H10 119.5 . . ? C1 C10 H10 119.5 . . ? C6 O11 C12 115.9(3) . . ? O11 C12 H12A 100(2) . . ? O11 C12 H12B 108(3) . . ? H12A C12 H12B 111(3) . . ? O11 C12 H12C 112(2) . . ? H12A C12 H12C 117(3) . . ? H12B C12 H12C 108(4) . . ? C15 C13 C14 109.4(3) . . ? C15 C13 C1 107.0(3) . . ? C14 C13 C1 115.7(3) . . ? C15 C13 H13 108.2 . . ? C14 C13 H13 108.2 . . ? C1 C13 H13 108.2 . . ? C13 C14 H14A 113(3) . . ? C13 C14 H14B 108(2) . . ? H14A C14 H14B 108(4) . . ? C13 C14 H14C 113(3) . . ? H14A C14 H14C 105(4) . . ? H14B C14 H14C 110(4) . . ? O16 C15 N17 121.6(3) . . ? O16 C15 C13 121.9(3) . . ? N17 C15 C13 116.5(3) . . ? C15 N17 C18 121.5(3) . . ? C15 N17 H17 122(3) . . ? C18 N17 H17 116(3) . . ? N17 C18 C19 110.1(3) . . ? N17 C18 C23 110.5(3) . . ? C19 C18 C23 113.1(3) . . ? N17 C18 H18 107.7 . . ? C19 C18 H18 107.7 . . ? C23 C18 H18 107.7 . . ? O20 C19 O21 124.2(3) . . ? O20 C19 C18 125.0(3) . . ? O21 C19 C18 110.8(3) . . ? C19 O21 C22 115.7(3) . . ? O21 C22 H22A 103(3) . . ? O21 C22 H22B 109(3) . . ? H22A C22 H22B 118(4) . . ? O21 C22 H22C 112(3) . . ? H22A C22 H22C 112(4) . . ? H22B C22 H22C 102(4) . . ? C24 C23 C18 111.3(3) . . ? C24 C23 H23A 109.4 . . ? C18 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C18 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C29 C24 C25 116.7(3) . . ? C29 C24 C23 122.9(3) . . ? C25 C24 C23 120.1(3) . . ? C26 C25 C24 121.8(3) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C27 120.2(3) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? O30 C27 C28 118.2(3) . . ? O30 C27 C26 122.6(3) . . ? C28 C27 C26 119.2(3) . . ? C29 C28 C27 120.0(3) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C24 122.1(3) . . ? C28 C29 H29 118.9 . . ? C24 C29 H29 118.9 . . ? C27 O30 H30 114(4) . . ? H1WA O1W H1WB 109(8) . . ? 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 C10 C1 C2 C3 -0.2(5) . . . . ? C13 C1 C2 C3 176.7(3) . . . . ? C1 C2 C3 C4 -179.0(3) . . . . ? C1 C2 C3 C8 0.3(5) . . . . ? C2 C3 C4 C5 179.4(3) . . . . ? C8 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 O11 177.2(3) . . . . ? C4 C5 C6 C7 -1.4(5) . . . . ? O11 C6 C7 C8 -177.7(3) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C4 C3 C8 C9 179.4(3) . . . . ? C2 C3 C8 C9 0.1(4) . . . . ? C4 C3 C8 C7 -0.8(4) . . . . ? C2 C3 C8 C7 179.9(3) . . . . ? C6 C7 C8 C9 -179.8(3) . . . . ? C6 C7 C8 C3 0.3(5) . . . . ? C3 C8 C9 C10 -0.4(5) . . . . ? C7 C8 C9 C10 179.7(3) . . . . ? C8 C9 C10 C1 0.5(5) . . . . ? C2 C1 C10 C9 -0.2(5) . . . . ? C13 C1 C10 C9 -177.1(3) . . . . ? C7 C6 O11 C12 4.5(5) . . . . ? C5 C6 O11 C12 -174.0(3) . . . . ? C2 C1 C13 C15 -69.7(4) . . . . ? C10 C1 C13 C15 107.1(4) . . . . ? C2 C1 C13 C14 168.1(3) . . . . ? C10 C1 C13 C14 -15.1(5) . . . . ? C14 C13 C15 O16 64.1(4) . . . . ? C1 C13 C15 O16 -62.0(4) . . . . ? C14 C13 C15 N17 -117.8(4) . . . . ? C1 C13 C15 N17 116.1(3) . . . . ? O16 C15 N17 C18 3.2(5) . . . . ? C13 C15 N17 C18 -174.9(3) . . . . ? C15 N17 C18 C19 -79.7(4) . . . . ? C15 N17 C18 C23 154.7(3) . . . . ? N17 C18 C19 O20 -41.6(5) . . . . ? C23 C18 C19 O20 82.5(4) . . . . ? N17 C18 C19 O21 139.2(3) . . . . ? C23 C18 C19 O21 -96.7(3) . . . . ? O20 C19 O21 C22 3.7(5) . . . . ? C18 C19 O21 C22 -177.1(3) . . . . ? N17 C18 C23 C24 -60.7(4) . . . . ? C19 C18 C23 C24 175.3(3) . . . . ? C18 C23 C24 C29 91.7(4) . . . . ? C18 C23 C24 C25 -82.5(4) . . . . ? C29 C24 C25 C26 0.2(5) . . . . ? C23 C24 C25 C26 174.8(3) . . . . ? C24 C25 C26 C27 -0.4(5) . . . . ? C25 C26 C27 O30 -180.0(3) . . . . ? C25 C26 C27 C28 0.1(5) . . . . ? O30 C27 C28 C29 -179.7(3) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C27 C28 C29 C24 -0.4(6) . . . . ? C25 C24 C29 C28 0.1(5) . . . . ? C23 C24 C29 C28 -174.2(3) . . . . ? 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 N17 H17 O16 0.86(6) 2.13(6) 2.958(4) 162(5) 1_655 O30 H30 O1W 0.90(7) 1.78(7) 2.673(4) 176(6) 1_554 O1W H1WA O30 0.81(4) 2.11(5) 2.914(4) 168(6) 1_456 O1W H1WB O16 0.84(5) 2.09(6) 2.881(4) 158(9) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 68.33 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.232 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 662960' ####################################################################### # # 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_uv01cj1n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N3 O4' _chemical_formula_sum 'C21 H23 N3 O4' _chemical_formula_weight 381.42 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.4293(4) _cell_length_b 8.9980(6) _cell_length_c 39.350(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1922.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1281 _cell_measurement_theta_min 3.439 _cell_measurement_theta_max 24.865 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'BRUKER SADABS' _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 'Smart-CCD-1000 BRUKER' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3919 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3919 _reflns_number_gt 3144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'Sir 2004' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^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 0.4(14) _refine_ls_number_reflns 3919 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 C1 C 0.1655(5) 0.1934(4) 0.10581(7) 0.0432(8) Uani 1 1 d . . . H1A H 0.0367 0.1454 0.0922 0.065 Uiso 1 1 calc R . . H1B H 0.2948 0.1210 0.1111 0.065 Uiso 1 1 calc R . . H1C H 0.2364 0.2762 0.0929 0.065 Uiso 1 1 calc R . . O2 O 0.0611(3) 0.2482(2) 0.13673(4) 0.0325(5) Uani 1 1 d . . . C3 C 0.2140(4) 0.3177(3) 0.15788(6) 0.0186(5) Uani 1 1 d . . . O4 O 0.4308(3) 0.3293(2) 0.15313(4) 0.0313(5) Uani 1 1 d . . . C5 C 0.0732(4) 0.3808(2) 0.18803(6) 0.0180(5) Uani 1 1 d . . . H5 H 0.198(5) 0.440(3) 0.2011(6) 0.022 Uiso 1 1 d . . . C6 C -0.0355(4) 0.2566(3) 0.21009(6) 0.0175(5) Uani 1 1 d . . . H6A H -0.1410 0.3006 0.2280 0.021 Uiso 1 1 calc R . . H6B H -0.1395 0.1911 0.1959 0.021 Uiso 1 1 calc R . . C7 C 0.1646(4) 0.1668(2) 0.22629(6) 0.0172(5) Uani 1 1 d . . . C8 C 0.2426(4) 0.0267(3) 0.21990(6) 0.0180(5) Uani 1 1 d . . . H8 H 0.1716 -0.0419 0.2044 0.022 Uiso 1 1 calc R . . N9 N 0.4451(4) 0.0031(2) 0.24034(5) 0.0190(4) Uani 1 1 d . . . H9 H 0.5350 -0.0782 0.2414 0.023 Uiso 1 1 calc R . . C10 C 0.4783(4) 0.1281(2) 0.25834(6) 0.0185(5) Uani 1 1 d . . . H10 H 0.6047 0.1409 0.2748 0.022 Uiso 1 1 calc R . . N11 N 0.3152(3) 0.2311(2) 0.25056(5) 0.0188(4) Uani 1 1 d . . . N12 N -0.1146(3) 0.4827(2) 0.17610(5) 0.0185(4) Uani 1 1 d . . . H12 H -0.2661 0.4501 0.1734 0.022 Uiso 1 1 calc R . . C13 C -0.0638(4) 0.6261(2) 0.16903(6) 0.0178(5) Uani 1 1 d . . . O14 O 0.1317(3) 0.68656(18) 0.17698(4) 0.0227(4) Uani 1 1 d . . . C15 C -0.2592(4) 0.7063(3) 0.14825(6) 0.0188(5) Uani 1 1 d . . . H15 H -0.408(5) 0.664(3) 0.1521(6) 0.023 Uiso 1 1 d . . . C16 C -0.2732(5) 0.8712(3) 0.15690(6) 0.0250(6) Uani 1 1 d . . . H16A H -0.4023 0.9182 0.1432 0.037 Uiso 1 1 calc R . . H16B H -0.1144 0.9183 0.1520 0.037 Uiso 1 1 calc R . . H16C H -0.3118 0.8830 0.1811 0.037 Uiso 1 1 calc R . . C17 C -0.1961(4) 0.6753(3) 0.11114(6) 0.0176(5) Uani 1 1 d . . . C18 C -0.3323(4) 0.5784(3) 0.09196(6) 0.0201(5) Uani 1 1 d . . . H18 H -0.4740 0.5333 0.1017 0.024 Uiso 1 1 calc R . . C19 C -0.2672(4) 0.5437(3) 0.05792(6) 0.0195(5) Uani 1 1 d . . . C20 C -0.4007(4) 0.4390(3) 0.03800(6) 0.0239(6) Uani 1 1 d . . . H20 H -0.5403 0.3909 0.0475 0.029 Uiso 1 1 calc R . . C21 C -0.3320(5) 0.4066(3) 0.00561(6) 0.0252(6) Uani 1 1 d . . . H21 H -0.4221 0.3354 -0.0071 0.030 Uiso 1 1 calc R . . C22 C -0.1276(4) 0.4784(3) -0.00907(6) 0.0203(5) Uani 1 1 d . . . O23 O -0.0802(3) 0.43725(19) -0.04211(4) 0.0271(4) Uani 1 1 d . . . C24 C 0.1302(4) 0.5039(3) -0.05786(7) 0.0310(6) Uani 1 1 d . . . H24A H 0.1459 0.4671 -0.0812 0.047 Uiso 1 1 calc R . . H24B H 0.2786 0.4782 -0.0450 0.047 Uiso 1 1 calc R . . H24C H 0.1101 0.6121 -0.0582 0.047 Uiso 1 1 calc R . . C25 C 0.0061(4) 0.5796(3) 0.00892(6) 0.0215(6) Uani 1 1 d . . . H25 H 0.1430 0.6277 -0.0013 0.026 Uiso 1 1 calc R . . C26 C -0.0598(4) 0.6130(3) 0.04313(6) 0.0199(5) Uani 1 1 d . . . C27 C 0.0787(4) 0.7123(3) 0.06348(6) 0.0236(6) Uani 1 1 d . . . H27 H 0.2191 0.7598 0.0540 0.028 Uiso 1 1 calc R . . C28 C 0.0156(4) 0.7415(3) 0.09632(6) 0.0208(5) Uani 1 1 d . . . H28 H 0.1145 0.8070 0.1095 0.025 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 C1 0.0391(16) 0.056(2) 0.0347(17) -0.0273(16) 0.0126(13) -0.0116(16) O2 0.0231(9) 0.0448(11) 0.0294(10) -0.0191(9) 0.0033(8) -0.0078(9) C3 0.0174(12) 0.0154(12) 0.0229(13) 0.0016(11) -0.0009(10) 0.0007(10) O4 0.0175(9) 0.0415(11) 0.0350(11) -0.0041(9) 0.0022(8) -0.0043(9) C5 0.0182(11) 0.0122(11) 0.0235(13) 0.0016(10) -0.0022(10) -0.0014(10) C6 0.0177(11) 0.0143(12) 0.0205(13) 0.0004(10) 0.0009(9) 0.0000(10) C7 0.0177(12) 0.0137(11) 0.0201(13) 0.0007(10) 0.0018(9) -0.0019(10) C8 0.0218(12) 0.0159(12) 0.0163(13) 0.0007(10) -0.0009(9) -0.0005(10) N9 0.0205(10) 0.0131(10) 0.0235(11) 0.0009(9) -0.0025(9) 0.0029(9) C10 0.0222(12) 0.0159(11) 0.0173(13) 0.0038(10) -0.0019(9) -0.0042(10) N11 0.0214(10) 0.0140(10) 0.0208(11) 0.0026(8) -0.0018(8) 0.0001(9) N12 0.0147(10) 0.0167(10) 0.0242(11) 0.0027(9) -0.0032(8) -0.0006(8) C13 0.0200(12) 0.0166(12) 0.0169(12) -0.0005(10) 0.0033(10) 0.0013(10) O14 0.0196(9) 0.0198(9) 0.0288(10) 0.0023(8) -0.0053(7) -0.0022(7) C15 0.0164(11) 0.0206(14) 0.0193(13) 0.0032(10) -0.0001(10) 0.0007(10) C16 0.0306(13) 0.0203(13) 0.0241(14) 0.0017(11) 0.0020(11) 0.0083(12) C17 0.0156(11) 0.0179(12) 0.0191(13) 0.0031(10) -0.0025(9) 0.0051(10) C18 0.0180(11) 0.0204(12) 0.0217(13) 0.0050(11) 0.0016(10) -0.0002(10) C19 0.0184(12) 0.0175(12) 0.0227(14) 0.0028(10) -0.0026(10) 0.0028(10) C20 0.0225(13) 0.0216(13) 0.0277(15) 0.0016(11) 0.0014(11) -0.0058(11) C21 0.0300(14) 0.0217(14) 0.0239(15) -0.0005(11) -0.0054(11) -0.0032(11) C22 0.0241(13) 0.0187(13) 0.0182(13) -0.0007(11) -0.0011(10) 0.0038(11) O23 0.0313(9) 0.0296(10) 0.0205(9) -0.0011(8) 0.0019(8) -0.0018(8) C24 0.0245(13) 0.0446(17) 0.0239(14) -0.0052(13) 0.0020(11) 0.0043(13) C25 0.0197(13) 0.0236(13) 0.0213(14) 0.0031(11) 0.0026(10) -0.0003(11) C26 0.0168(11) 0.0211(13) 0.0218(13) 0.0036(11) 0.0013(10) 0.0030(11) C27 0.0170(11) 0.0250(13) 0.0289(14) 0.0013(11) 0.0020(10) -0.0024(11) C28 0.0191(12) 0.0207(12) 0.0226(14) -0.0013(11) -0.0045(9) -0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.430(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.331(3) . ? C3 O4 1.196(3) . ? C3 C5 1.521(3) . ? C5 N12 1.449(3) . ? C5 C6 1.533(3) . ? C5 H5 1.00(2) . ? C6 C7 1.496(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.353(3) . ? C7 N11 1.384(3) . ? C8 N9 1.379(3) . ? C8 H8 0.9500 . ? N9 C10 1.342(3) . ? N9 H9 0.8800 . ? C10 N11 1.318(3) . ? C10 H10 0.9500 . ? N12 C13 1.348(3) . ? N12 H12 0.8800 . ? C13 O14 1.233(3) . ? C13 C15 1.522(3) . ? C15 C16 1.524(3) . ? C15 C17 1.525(3) . ? C15 H15 0.90(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.370(3) . ? C17 C28 1.420(3) . ? C18 C19 1.420(3) . ? C18 H18 0.9500 . ? C19 C26 1.412(3) . ? C19 C20 1.424(3) . ? C20 C21 1.359(3) . ? C20 H20 0.9500 . ? C21 C22 1.407(3) . ? C21 H21 0.9500 . ? C22 C25 1.363(3) . ? C22 O23 1.376(3) . ? O23 C24 1.431(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.425(3) . ? C25 H25 0.9500 . ? C26 C27 1.416(3) . ? C27 C28 1.362(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 116.5(2) . . ? O4 C3 O2 123.9(2) . . ? O4 C3 C5 125.7(2) . . ? O2 C3 C5 110.43(19) . . ? N12 C5 C3 109.70(19) . . ? N12 C5 C6 111.98(18) . . ? C3 C5 C6 111.28(19) . . ? N12 C5 H5 108.0(14) . . ? C3 C5 H5 104.8(13) . . ? C6 C5 H5 110.8(14) . . ? C7 C6 C5 110.81(18) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 N11 109.4(2) . . ? C8 C7 C6 130.6(2) . . ? N11 C7 C6 119.8(2) . . ? C7 C8 N9 106.6(2) . . ? C7 C8 H8 126.7 . . ? N9 C8 H8 126.7 . . ? C10 N9 C8 106.59(19) . . ? C10 N9 H9 126.7 . . ? C8 N9 H9 126.7 . . ? N11 C10 N9 112.1(2) . . ? N11 C10 H10 123.9 . . ? N9 C10 H10 123.9 . . ? C10 N11 C7 105.28(19) . . ? C13 N12 C5 121.91(19) . . ? C13 N12 H12 119.0 . . ? C5 N12 H12 119.0 . . ? O14 C13 N12 123.1(2) . . ? O14 C13 C15 121.8(2) . . ? N12 C13 C15 115.0(2) . . ? C13 C15 C16 112.1(2) . . ? C13 C15 C17 105.72(18) . . ? C16 C15 C17 113.78(19) . . ? C13 C15 H15 109.4(16) . . ? C16 C15 H15 109.1(15) . . ? C17 C15 H15 106.5(15) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C28 118.5(2) . . ? C18 C17 C15 121.5(2) . . ? C28 C17 C15 119.9(2) . . ? C17 C18 C19 121.7(2) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C26 C19 C18 119.3(2) . . ? C26 C19 C20 118.1(2) . . ? C18 C19 C20 122.6(2) . . ? C21 C20 C19 121.2(2) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 120.2(2) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C25 C22 O23 124.8(2) . . ? C25 C22 C21 120.9(2) . . ? O23 C22 C21 114.3(2) . . ? C22 O23 C24 116.47(19) . . ? O23 C24 H24A 109.5 . . ? O23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 C26 119.8(2) . . ? C22 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C19 C26 C27 118.0(2) . . ? C19 C26 C25 119.8(2) . . ? C27 C26 C25 122.3(2) . . ? C28 C27 C26 121.6(2) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C27 C28 C17 120.8(2) . . ? C27 C28 H28 119.6 . . ? C17 C28 H28 119.6 . . ? 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 C1 O2 C3 O4 -3.8(4) . . . . ? C1 O2 C3 C5 175.2(2) . . . . ? O4 C3 C5 N12 120.6(3) . . . . ? O2 C3 C5 N12 -58.5(2) . . . . ? O4 C3 C5 C6 -114.9(3) . . . . ? O2 C3 C5 C6 66.0(2) . . . . ? N12 C5 C6 C7 -171.46(19) . . . . ? C3 C5 C6 C7 65.4(2) . . . . ? C5 C6 C7 C8 -108.3(3) . . . . ? C5 C6 C7 N11 66.9(3) . . . . ? N11 C7 C8 N9 -0.2(2) . . . . ? C6 C7 C8 N9 175.3(2) . . . . ? C7 C8 N9 C10 0.8(2) . . . . ? C8 N9 C10 N11 -1.1(3) . . . . ? N9 C10 N11 C7 1.0(3) . . . . ? C8 C7 N11 C10 -0.4(2) . . . . ? C6 C7 N11 C10 -176.6(2) . . . . ? C3 C5 N12 C13 -83.9(3) . . . . ? C6 C5 N12 C13 152.0(2) . . . . ? C5 N12 C13 O14 -11.6(3) . . . . ? C5 N12 C13 C15 164.5(2) . . . . ? O14 C13 C15 C16 -35.4(3) . . . . ? N12 C13 C15 C16 148.5(2) . . . . ? O14 C13 C15 C17 89.1(3) . . . . ? N12 C13 C15 C17 -87.0(2) . . . . ? C13 C15 C17 C18 106.2(2) . . . . ? C16 C15 C17 C18 -130.3(2) . . . . ? C13 C15 C17 C28 -70.4(3) . . . . ? C16 C15 C17 C28 53.0(3) . . . . ? C28 C17 C18 C19 -0.2(3) . . . . ? C15 C17 C18 C19 -176.9(2) . . . . ? C17 C18 C19 C26 -1.4(3) . . . . ? C17 C18 C19 C20 177.5(2) . . . . ? C26 C19 C20 C21 -0.2(3) . . . . ? C18 C19 C20 C21 -179.1(2) . . . . ? C19 C20 C21 C22 -0.9(4) . . . . ? C20 C21 C22 C25 0.8(3) . . . . ? C20 C21 C22 O23 -179.0(2) . . . . ? C25 C22 O23 C24 1.9(3) . . . . ? C21 C22 O23 C24 -178.2(2) . . . . ? O23 C22 C25 C26 -179.8(2) . . . . ? C21 C22 C25 C26 0.4(3) . . . . ? C18 C19 C26 C27 1.5(3) . . . . ? C20 C19 C26 C27 -177.4(2) . . . . ? C18 C19 C26 C25 -179.6(2) . . . . ? C20 C19 C26 C25 1.5(3) . . . . ? C22 C25 C26 C19 -1.6(3) . . . . ? C22 C25 C26 C27 177.2(2) . . . . ? C19 C26 C27 C28 -0.2(3) . . . . ? C25 C26 C27 C28 -179.0(2) . . . . ? C26 C27 C28 C17 -1.4(4) . . . . ? C18 C17 C28 C27 1.6(3) . . . . ? C15 C17 C28 C27 178.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.247 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 662964' ####################################################################### # # 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_2006uv02cj02n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N3 O4' _chemical_formula_weight 380.42 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5041(4) _cell_length_b 5.1979(3) _cell_length_c 24.1640(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.664(3) _cell_angle_gamma 90.00 _cell_volume 941.51(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8303 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2771 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 60.05 _reflns_number_total 2771 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0852P)^2^+0.2877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(3) _refine_ls_number_reflns 2771 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 C1 C 1.1496(3) 0.1332(6) 0.43023(11) 0.0347(7) Uani 1 1 d . . . C2 C 1.0467(4) -0.0733(7) 0.44878(11) 0.0410(8) Uani 1 1 d . . . H2 H 1.0844 -0.1649 0.4813 0.049 Uiso 1 1 calc R . . C3 C 0.8933(4) -0.1424(7) 0.42031(11) 0.0400(7) Uani 1 1 d . . . H3 H 0.8248 -0.2816 0.4334 0.048 Uiso 1 1 calc R . . C4 C 0.8341(3) -0.0102(6) 0.37156(10) 0.0296(6) Uani 1 1 d . . . C5 C 0.9354(3) 0.2027(6) 0.35424(10) 0.0291(6) Uani 1 1 d . . . C6 C 1.0944(3) 0.2729(6) 0.38481(10) 0.0321(7) Uani 1 1 d . . . H6 H 1.1621 0.4167 0.3736 0.039 Uiso 1 1 calc R . . C7 C 0.6808(3) -0.0873(6) 0.33896(10) 0.0312(6) Uani 1 1 d . . . H7 H 0.6123 -0.2287 0.3509 0.037 Uiso 1 1 calc R . . C8 C 0.6288(3) 0.0365(5) 0.29072(10) 0.0265(6) Uani 1 1 d . . . C9 C 0.7298(3) 0.2518(6) 0.27469(11) 0.0324(6) Uani 1 1 d . . . H9 H 0.6947 0.3426 0.2419 0.039 Uiso 1 1 calc R . . C10 C 0.8772(3) 0.3320(6) 0.30559(10) 0.0329(6) Uani 1 1 d . . . H10 H 0.9415 0.4781 0.2939 0.039 Uiso 1 1 calc R . . O11 O 1.3051(2) 0.1773(5) 0.46122(8) 0.0434(6) Uani 1 1 d . . . C12 C 1.4212(4) 0.3725(8) 0.44199(13) 0.0508(9) Uani 1 1 d . . . H12A H 1.4563 0.3296 0.4045 0.076 Uiso 1 1 calc R . . H12B H 1.5278 0.3831 0.4669 0.076 Uiso 1 1 calc R . . H12C H 1.3592 0.5384 0.4414 0.076 Uiso 1 1 calc R . . C13 C 0.4722(3) -0.0655(5) 0.25393(10) 0.0259(6) Uani 1 1 d . . . H13 H 0.5131 -0.2249 0.2352 0.031 Uiso 1 1 calc R . . C14 C 0.4171(3) 0.1287(5) 0.20917(10) 0.0256(6) Uani 1 1 d . . . C15 C 0.3105(3) -0.1360(6) 0.28693(11) 0.0347(7) Uani 1 1 d . . . H15A H 0.2731 0.0143 0.3080 0.052 Uiso 1 1 calc R . . H15B H 0.3423 -0.2766 0.3126 0.052 Uiso 1 1 calc R . . H15C H 0.2124 -0.1909 0.2614 0.052 Uiso 1 1 calc R . . O16 O 0.3206(2) 0.3157(4) 0.21959(7) 0.0322(5) Uani 1 1 d . . . N17 N 0.4797(2) 0.0861(4) 0.15900(8) 0.0238(5) Uani 1 1 d . . . C18 C 0.4450(3) 0.2567(5) 0.11264(10) 0.0252(6) Uani 1 1 d . . . H18 H 0.3976 0.4215 0.1274 0.030 Uiso 1 1 calc R . . C19 C 0.6181(3) 0.3200(6) 0.08299(10) 0.0287(6) Uani 1 1 d . . . H19A H 0.6646 0.1607 0.0664 0.034 Uiso 1 1 calc R . . H19B H 0.5902 0.4431 0.0526 0.034 Uiso 1 1 calc R . . C20 C 0.7584(3) 0.4326(5) 0.12145(10) 0.0261(6) Uani 1 1 d . . . N21 N 0.7381(3) 0.6671(5) 0.14763(8) 0.0279(5) Uani 1 1 d . . . C22 C 0.8867(3) 0.6990(6) 0.17884(10) 0.0292(6) Uani 1 1 d . . . H22 H 0.9094 0.8439 0.2020 0.035 Uiso 1 1 calc R . . N23 N 1.0020(3) 0.5012(5) 0.17381(9) 0.0292(5) Uani 1 1 d . . . C24 C 0.9204(3) 0.3296(5) 0.13745(10) 0.0264(6) Uani 1 1 d . . . H24 H 0.9676 0.1702 0.1257 0.032 Uiso 1 1 calc R . . C25 C 0.3075(3) 0.1533(5) 0.06981(10) 0.0254(6) Uani 1 1 d . . . O26 O 0.2322(2) -0.0661(4) 0.08530(7) 0.0281(5) Uani 1 1 d . . . C27 C 0.0969(3) -0.1697(6) 0.04659(10) 0.0318(6) Uani 1 1 d . . . H27A H -0.0033 -0.0491 0.0428 0.048 Uiso 1 1 calc R . . H27B H 0.0547 -0.3350 0.0604 0.048 Uiso 1 1 calc R . . H27C H 0.1481 -0.1949 0.0104 0.048 Uiso 1 1 calc R . . O28 O 0.2717(2) 0.2608(4) 0.02647(7) 0.0343(5) Uani 1 1 d . . . H17 H 0.553(4) -0.063(7) 0.1517(12) 0.041 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0266(13) 0.046(2) 0.0311(13) -0.0069(13) -0.0064(10) 0.0039(12) C2 0.0400(15) 0.049(2) 0.0332(14) 0.0066(14) -0.0087(12) 0.0023(14) C3 0.0404(15) 0.0434(19) 0.0355(15) 0.0044(14) -0.0051(11) -0.0042(14) C4 0.0273(12) 0.0322(17) 0.0290(12) 0.0013(12) -0.0014(10) 0.0027(12) C5 0.0274(12) 0.0314(16) 0.0285(12) -0.0043(12) -0.0001(10) 0.0015(12) C6 0.0276(12) 0.0360(17) 0.0325(13) -0.0040(12) -0.0024(10) -0.0013(12) C7 0.0305(13) 0.0318(17) 0.0310(13) 0.0009(12) -0.0020(10) -0.0043(12) C8 0.0221(12) 0.0277(15) 0.0295(13) -0.0028(11) -0.0017(10) 0.0036(11) C9 0.0273(12) 0.0358(17) 0.0335(13) 0.0044(12) -0.0066(10) -0.0020(12) C10 0.0315(13) 0.0310(16) 0.0355(14) 0.0035(12) -0.0035(11) -0.0066(12) O11 0.0321(9) 0.0598(15) 0.0372(10) -0.0002(10) -0.0119(8) -0.0027(10) C12 0.0354(15) 0.066(2) 0.0496(17) 0.0008(18) -0.0118(13) -0.0108(17) C13 0.0224(12) 0.0270(15) 0.0281(12) -0.0023(11) -0.0020(9) -0.0022(10) C14 0.0177(11) 0.0279(16) 0.0310(13) -0.0022(11) -0.0018(9) -0.0010(11) C15 0.0260(13) 0.0429(19) 0.0350(13) 0.0005(13) 0.0001(10) -0.0078(12) O16 0.0274(9) 0.0344(12) 0.0346(9) -0.0031(9) -0.0015(7) 0.0083(9) N17 0.0208(10) 0.0245(13) 0.0259(11) -0.0012(9) -0.0018(8) 0.0014(9) C18 0.0234(12) 0.0223(14) 0.0299(12) -0.0010(11) 0.0003(9) -0.0006(11) C19 0.0230(12) 0.0320(16) 0.0310(13) 0.0020(12) 0.0004(9) -0.0009(11) C20 0.0203(11) 0.0257(15) 0.0325(12) 0.0000(12) 0.0021(9) -0.0011(10) N21 0.0220(10) 0.0278(13) 0.0337(11) -0.0002(10) -0.0009(8) 0.0018(9) C22 0.0270(12) 0.0237(15) 0.0369(14) 0.0007(12) 0.0016(10) 0.0011(11) N23 0.0253(10) 0.0259(13) 0.0367(11) 0.0031(10) 0.0031(9) -0.0002(9) C24 0.0237(12) 0.0227(14) 0.0330(13) -0.0017(12) 0.0022(10) 0.0003(11) C25 0.0211(12) 0.0237(15) 0.0313(13) 0.0001(11) 0.0003(10) 0.0026(11) O26 0.0243(8) 0.0278(11) 0.0318(9) -0.0014(8) -0.0044(7) -0.0035(8) C27 0.0269(13) 0.0365(17) 0.0314(13) -0.0024(13) -0.0054(10) -0.0056(12) O28 0.0332(10) 0.0349(12) 0.0340(10) 0.0069(9) -0.0093(7) -0.0042(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.364(4) . ? C1 O11 1.376(3) . ? C1 C2 1.408(4) . ? C2 C3 1.361(4) . ? C2 H2 0.9500 . ? C3 C4 1.417(4) . ? C3 H3 0.9500 . ? C4 C5 1.417(4) . ? C4 C7 1.421(4) . ? C5 C10 1.406(4) . ? C5 C6 1.422(4) . ? C6 H6 0.9500 . ? C7 C8 1.372(4) . ? C7 H7 0.9500 . ? C8 C9 1.416(4) . ? C8 C13 1.534(3) . ? C9 C10 1.370(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O11 C12 1.429(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.522(4) . ? C13 C15 1.527(3) . ? C13 H13 1.0000 . ? C14 O16 1.245(3) . ? C14 N17 1.339(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N17 C18 1.443(3) . ? N17 H17 0.97(3) . ? C18 C25 1.525(3) . ? C18 C19 1.548(3) . ? C18 H18 1.0000 . ? C19 C20 1.492(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C24 1.367(4) . ? C20 N21 1.385(4) . ? N21 C22 1.327(3) . ? C22 N23 1.353(3) . ? C22 H22 0.9500 . ? N23 C24 1.375(3) . ? C24 H24 0.9500 . ? C25 O28 1.206(3) . ? C25 O26 1.334(3) . ? O26 C27 1.452(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 C6 C1 O11 124.6(3) . . ? C6 C1 C2 120.8(2) . . ? O11 C1 C2 114.7(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 118.2(2) . . ? C5 C4 C7 119.2(2) . . ? C3 C4 C7 122.6(3) . . ? C10 C5 C4 118.1(2) . . ? C10 C5 C6 122.2(2) . . ? C4 C5 C6 119.7(2) . . ? C1 C6 C5 119.9(3) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C4 122.0(3) . . ? C8 C7 H7 119.0 . . ? C4 C7 H7 119.0 . . ? C7 C8 C9 117.9(2) . . ? C7 C8 C13 120.7(2) . . ? C9 C8 C13 121.3(2) . . ? C10 C9 C8 121.4(2) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C5 121.4(3) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? C1 O11 C12 117.1(2) . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 109.5(2) . . ? C14 C13 C8 111.0(2) . . ? C15 C13 C8 112.70(19) . . ? C14 C13 H13 107.8 . . ? C15 C13 H13 107.8 . . ? C8 C13 H13 107.8 . . ? O16 C14 N17 123.0(2) . . ? O16 C14 C13 121.0(2) . . ? N17 C14 C13 116.0(2) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 N17 C18 122.9(2) . . ? C14 N17 H17 121.4(18) . . ? C18 N17 H17 115.7(18) . . ? N17 C18 C25 113.7(2) . . ? N17 C18 C19 111.43(19) . . ? C25 C18 C19 108.46(19) . . ? N17 C18 H18 107.7 . . ? C25 C18 H18 107.7 . . ? C19 C18 H18 107.7 . . ? C20 C19 C18 112.23(19) . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C24 C20 N21 109.3(2) . . ? C24 C20 C19 128.0(3) . . ? N21 C20 C19 122.7(2) . . ? C22 N21 C20 105.2(2) . . ? N21 C22 N23 112.2(2) . . ? N21 C22 H22 123.9 . . ? N23 C22 H22 123.9 . . ? C22 N23 C24 106.4(2) . . ? C20 C24 N23 106.9(2) . . ? C20 C24 H24 126.6 . . ? N23 C24 H24 126.6 . . ? O28 C25 O26 124.0(2) . . ? O28 C25 C18 122.9(2) . . ? O26 C25 C18 113.1(2) . . ? C25 O26 C27 115.39(19) . . ? O26 C27 H27A 109.5 . . ? O26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C6 C1 C2 C3 2.4(4) . . . . ? O11 C1 C2 C3 -177.5(3) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 -2.3(4) . . . . ? C2 C3 C4 C7 176.0(3) . . . . ? C3 C4 C5 C10 179.4(3) . . . . ? C7 C4 C5 C10 1.1(4) . . . . ? C3 C4 C5 C6 1.8(4) . . . . ? C7 C4 C5 C6 -176.5(2) . . . . ? O11 C1 C6 C5 177.0(3) . . . . ? C2 C1 C6 C5 -2.9(4) . . . . ? C10 C5 C6 C1 -176.8(3) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C5 C4 C7 C8 0.8(4) . . . . ? C3 C4 C7 C8 -177.5(3) . . . . ? C4 C7 C8 C9 -2.0(4) . . . . ? C4 C7 C8 C13 174.7(2) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? C13 C8 C9 C10 -175.4(2) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? C4 C5 C10 C9 -1.7(4) . . . . ? C6 C5 C10 C9 175.8(3) . . . . ? C6 C1 O11 C12 -4.3(4) . . . . ? C2 C1 O11 C12 175.6(3) . . . . ? C7 C8 C13 C14 169.2(2) . . . . ? C9 C8 C13 C14 -14.2(3) . . . . ? C7 C8 C13 C15 46.0(3) . . . . ? C9 C8 C13 C15 -137.4(3) . . . . ? C15 C13 C14 O16 44.7(3) . . . . ? C8 C13 C14 O16 -80.4(3) . . . . ? C15 C13 C14 N17 -135.8(2) . . . . ? C8 C13 C14 N17 99.2(2) . . . . ? O16 C14 N17 C18 1.7(4) . . . . ? C13 C14 N17 C18 -177.8(2) . . . . ? C14 N17 C18 C25 -105.1(3) . . . . ? C14 N17 C18 C19 132.0(2) . . . . ? N17 C18 C19 C20 -56.3(3) . . . . ? C25 C18 C19 C20 177.7(2) . . . . ? C18 C19 C20 C24 114.9(3) . . . . ? C18 C19 C20 N21 -64.0(3) . . . . ? C24 C20 N21 C22 -0.4(3) . . . . ? C19 C20 N21 C22 178.7(2) . . . . ? C20 N21 C22 N23 0.8(3) . . . . ? N21 C22 N23 C24 -0.8(3) . . . . ? N21 C20 C24 N23 -0.1(3) . . . . ? C19 C20 C24 N23 -179.1(2) . . . . ? C22 N23 C24 C20 0.5(3) . . . . ? N17 C18 C25 O28 -174.4(2) . . . . ? C19 C18 C25 O28 -49.8(3) . . . . ? N17 C18 C25 O26 5.6(3) . . . . ? C19 C18 C25 O26 130.2(2) . . . . ? O28 C25 O26 C27 -1.5(3) . . . . ? C18 C25 O26 C27 178.53(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.489 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.180 _database_code_depnum_ccdc_archive 'CCDC 662965'