data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H34 N2 O4' _chemical_formula_weight 522.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.536(2) _cell_length_b 24.036(5) _cell_length_c 11.377(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.09(3) _cell_angle_gamma 90.00 _cell_volume 2827.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 21188 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9486 _exptl_absorpt_correction_T_max 0.9660 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RaxisRapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21188 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0776 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5679 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0486P)^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_number_reflns 5679 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.03288(13) 0.30820(6) 0.43871(14) 0.0401(4) Uani 1 1 d . . . O2 O 0.00951(12) 0.21383(6) 0.47168(13) 0.0403(4) Uani 1 1 d . . . O3 O -0.08199(16) 0.41014(7) 0.08169(15) 0.0584(5) Uani 1 1 d . . . H3A H -0.0028 0.4118 0.0948 0.088 Uiso 1 1 calc R . . O4 O 0.23575(16) 0.06787(7) 0.32130(17) 0.0696(6) Uani 1 1 d . . . H4A H 0.1616 0.0601 0.2884 0.104 Uiso 1 1 calc R . . N1 N -0.0017(2) 0.54178(10) 0.3159(2) 0.0649(7) Uani 1 1 d . . . N2 N 0.7225(2) 0.44385(11) 0.8991(2) 0.0691(7) Uani 1 1 d . . . C1 C 0.2345(2) 0.11428(10) 0.3895(2) 0.0463(6) Uani 1 1 d . . . C2 C 0.3522(2) 0.13363(10) 0.4513(2) 0.0500(7) Uani 1 1 d . . . H2B H 0.4285 0.1155 0.4449 0.060 Uiso 1 1 calc R . . C3 C 0.3550(2) 0.18018(10) 0.5227(2) 0.0451(6) Uani 1 1 d . . . H3B H 0.4346 0.1926 0.5646 0.054 Uiso 1 1 calc R . . C4 C 0.2435(2) 0.20966(9) 0.53498(19) 0.0371(5) Uani 1 1 d . . . C5 C 0.2499(2) 0.25939(9) 0.6186(2) 0.0413(6) Uani 1 1 d . . . C6 C 0.3277(2) 0.24417(13) 0.7417(2) 0.0672(8) Uani 1 1 d . . . H6A H 0.4148 0.2352 0.7349 0.101 Uiso 1 1 calc R . . H6B H 0.2888 0.2126 0.7725 0.101 Uiso 1 1 calc R . . H6C H 0.3285 0.2751 0.7951 0.101 Uiso 1 1 calc R . . C7 C 0.3123(2) 0.31028(10) 0.5707(3) 0.0599(7) Uani 1 1 d . . . H7A H 0.3985 0.3011 0.5613 0.090 Uiso 1 1 calc R . . H7B H 0.3156 0.3406 0.6262 0.090 Uiso 1 1 calc R . . H7C H 0.2619 0.3210 0.4946 0.090 Uiso 1 1 calc R . . C8 C 0.11165(19) 0.27299(9) 0.6338(2) 0.0384(6) Uani 1 1 d . . . H8A H 0.0901 0.2488 0.6954 0.046 Uiso 1 1 calc R . . H8B H 0.1105 0.3109 0.6628 0.046 Uiso 1 1 calc R . . C9 C 0.00744(19) 0.26736(9) 0.5238(2) 0.0353(5) Uani 1 1 d . . . C10 C -0.12518(19) 0.27612(9) 0.5535(2) 0.0413(6) Uani 1 1 d . . . H10A H -0.1423 0.2456 0.6041 0.050 Uiso 1 1 calc R . . H10B H -0.1229 0.3100 0.6002 0.050 Uiso 1 1 calc R . . C11 C -0.23808(19) 0.28020(9) 0.4474(2) 0.0417(6) Uani 1 1 d . . . C12 C -0.2814(2) 0.22236(10) 0.3967(2) 0.0574(7) Uani 1 1 d . . . H12A H -0.2116 0.2049 0.3675 0.086 Uiso 1 1 calc R . . H12B H -0.3544 0.2263 0.3323 0.086 Uiso 1 1 calc R . . H12C H -0.3051 0.1999 0.4588 0.086 Uiso 1 1 calc R . . C13 C -0.3507(2) 0.30748(12) 0.4947(2) 0.0649(8) Uani 1 1 d . . . H13A H -0.3243 0.3434 0.5276 0.097 Uiso 1 1 calc R . . H13B H -0.3744 0.2844 0.5560 0.097 Uiso 1 1 calc R . . H13C H -0.4236 0.3116 0.4302 0.097 Uiso 1 1 calc R . . C14 C -0.19730(19) 0.31534(8) 0.3512(2) 0.0364(5) Uani 1 1 d . . . C15 C -0.2857(2) 0.33858(9) 0.2573(2) 0.0450(6) Uani 1 1 d . . . H15A H -0.3732 0.3322 0.2548 0.054 Uiso 1 1 calc R . . C16 C -0.2511(2) 0.37028(9) 0.1685(2) 0.0484(6) Uani 1 1 d . . . H16A H -0.3142 0.3855 0.1086 0.058 Uiso 1 1 calc R . . C17 C -0.1210(2) 0.37951(9) 0.1686(2) 0.0427(6) Uani 1 1 d . . . C18 C -0.0300(2) 0.35694(9) 0.2597(2) 0.0389(6) Uani 1 1 d . . . H18A H 0.0575 0.3626 0.2605 0.047 Uiso 1 1 calc R . . C19 C -0.0675(2) 0.32593(8) 0.3499(2) 0.0359(5) Uani 1 1 d . . . C20 C 0.12835(19) 0.18951(8) 0.4697(2) 0.0342(5) Uani 1 1 d . . . C21 C 0.1223(2) 0.14235(9) 0.3992(2) 0.0405(6) Uani 1 1 d . . . H21A H 0.0428 0.1295 0.3582 0.049 Uiso 1 1 calc R . . C22 C 0.0361(3) 0.56397(11) 0.4250(3) 0.0623(8) Uani 1 1 d . . . H22A H -0.0144 0.5921 0.4483 0.075 Uiso 1 1 calc R . . C23 C 0.1447(3) 0.54775(10) 0.5042(3) 0.0544(7) Uani 1 1 d . . . H23A H 0.1668 0.5649 0.5786 0.065 Uiso 1 1 calc R . . C24 C 0.2214(2) 0.50555(10) 0.4727(2) 0.0488(6) Uani 1 1 d . . . C25 C 0.1816(3) 0.48220(11) 0.3603(3) 0.0628(8) Uani 1 1 d . . . H25A H 0.2289 0.4534 0.3350 0.075 Uiso 1 1 calc R . . C26 C 0.0714(3) 0.50172(13) 0.2860(3) 0.0668(8) Uani 1 1 d . . . H26A H 0.0474 0.4857 0.2106 0.080 Uiso 1 1 calc R . . C27 C 0.3388(3) 0.48485(10) 0.5519(3) 0.0551(7) Uani 1 1 d . . . H27A H 0.3812 0.4553 0.5235 0.066 Uiso 1 1 calc R . . C28 C 0.3892(3) 0.50372(11) 0.6576(3) 0.0587(7) Uani 1 1 d . . . H28A H 0.3479 0.5338 0.6853 0.070 Uiso 1 1 calc R . . C29 C 0.5047(3) 0.48226(11) 0.7376(3) 0.0532(7) Uani 1 1 d . . . C30 C 0.5547(3) 0.51017(13) 0.8407(3) 0.0772(9) Uani 1 1 d . . . H30A H 0.5166 0.5432 0.8587 0.093 Uiso 1 1 calc R . . C31 C 0.6608(3) 0.48975(14) 0.9178(3) 0.0827(10) Uani 1 1 d . . . H31A H 0.6911 0.5096 0.9877 0.099 Uiso 1 1 calc R . . C32 C 0.6747(3) 0.41710(12) 0.7981(3) 0.0671(8) Uani 1 1 d . . . H32A H 0.7162 0.3848 0.7812 0.081 Uiso 1 1 calc R . . C33 C 0.5676(3) 0.43425(11) 0.7169(2) 0.0585(7) Uani 1 1 d . . . H33A H 0.5381 0.4134 0.6482 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0298(8) 0.0513(9) 0.0380(10) 0.0093(8) 0.0034(8) 0.0003(7) O2 0.0300(8) 0.0439(9) 0.0440(11) -0.0062(7) -0.0006(8) 0.0023(6) O3 0.0599(11) 0.0658(11) 0.0497(12) 0.0127(9) 0.0110(10) -0.0005(9) O4 0.0611(11) 0.0695(12) 0.0725(14) -0.0299(11) -0.0014(11) 0.0170(9) N1 0.0677(16) 0.0590(15) 0.0595(18) 0.0165(13) -0.0092(15) -0.0127(12) N2 0.0761(17) 0.0738(17) 0.0526(17) 0.0164(14) -0.0002(15) 0.0075(14) C1 0.0470(15) 0.0492(14) 0.0407(16) -0.0053(12) 0.0028(14) 0.0094(11) C2 0.0384(14) 0.0654(17) 0.0439(17) -0.0020(13) 0.0018(14) 0.0150(12) C3 0.0332(12) 0.0618(15) 0.0372(15) -0.0006(12) -0.0010(13) 0.0043(11) C4 0.0330(12) 0.0481(13) 0.0287(14) 0.0040(11) 0.0026(12) 0.0032(10) C5 0.0306(12) 0.0576(15) 0.0327(15) -0.0021(11) -0.0016(12) 0.0021(10) C6 0.0500(16) 0.105(2) 0.0377(17) -0.0157(16) -0.0130(16) 0.0142(15) C7 0.0396(13) 0.0640(17) 0.077(2) -0.0119(15) 0.0135(15) -0.0128(12) C8 0.0349(12) 0.0487(14) 0.0304(14) -0.0002(10) 0.0028(12) 0.0010(10) C9 0.0332(12) 0.0413(13) 0.0303(14) 0.0004(10) 0.0032(12) -0.0006(9) C10 0.0358(13) 0.0483(14) 0.0421(16) 0.0009(11) 0.0131(13) 0.0001(10) C11 0.0270(12) 0.0503(14) 0.0469(16) 0.0013(12) 0.0053(13) 0.0003(10) C12 0.0438(14) 0.0599(16) 0.0621(19) 0.0070(14) -0.0058(15) -0.0130(12) C13 0.0359(14) 0.099(2) 0.0621(19) 0.0018(16) 0.0152(15) 0.0095(13) C14 0.0299(12) 0.0399(13) 0.0377(15) -0.0050(11) 0.0021(12) 0.0036(9) C15 0.0330(12) 0.0522(14) 0.0471(17) -0.0073(13) 0.0005(14) 0.0007(11) C16 0.0472(15) 0.0507(15) 0.0419(16) 0.0002(12) -0.0052(14) 0.0073(11) C17 0.0506(15) 0.0411(13) 0.0346(16) 0.0001(11) 0.0034(14) 0.0019(11) C18 0.0330(12) 0.0443(13) 0.0386(15) -0.0010(11) 0.0049(13) -0.0002(10) C19 0.0344(12) 0.0346(12) 0.0377(15) -0.0035(10) 0.0042(13) 0.0036(9) C20 0.0298(12) 0.0423(12) 0.0297(13) 0.0036(10) 0.0035(11) 0.0033(9) C21 0.0348(12) 0.0469(14) 0.0362(15) -0.0022(11) -0.0022(12) 0.0014(10) C22 0.0649(19) 0.0451(15) 0.070(2) 0.0070(15) -0.0028(19) -0.0026(13) C23 0.0600(17) 0.0484(15) 0.0497(19) -0.0015(13) -0.0024(17) -0.0041(13) C24 0.0527(16) 0.0472(15) 0.0429(18) 0.0065(13) 0.0004(16) -0.0088(12) C25 0.070(2) 0.0629(18) 0.052(2) -0.0028(15) 0.0035(19) -0.0059(14) C26 0.073(2) 0.075(2) 0.047(2) 0.0026(16) -0.0027(19) -0.0188(17) C27 0.0598(17) 0.0517(16) 0.052(2) -0.0010(14) 0.0070(17) -0.0009(12) C28 0.0633(18) 0.0604(17) 0.051(2) -0.0041(15) 0.0062(18) 0.0059(14) C29 0.0553(16) 0.0571(17) 0.0455(18) 0.0041(13) 0.0056(16) 0.0022(13) C30 0.085(2) 0.081(2) 0.056(2) -0.0132(17) -0.008(2) 0.0273(17) C31 0.096(2) 0.089(2) 0.051(2) -0.0112(18) -0.013(2) 0.016(2) C32 0.075(2) 0.0537(17) 0.068(2) 0.0127(16) 0.004(2) 0.0090(14) C33 0.0683(18) 0.0531(16) 0.0468(18) 0.0036(14) -0.0075(17) -0.0030(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C19 1.382(2) . ? O1 C9 1.439(2) . ? O2 C20 1.386(2) . ? O2 C9 1.418(2) . ? O3 C17 1.358(3) . ? O4 C1 1.360(3) . ? N1 C26 1.318(4) . ? N1 C22 1.339(3) . ? N2 C32 1.329(3) . ? N2 C31 1.318(4) . ? C1 C21 1.383(3) . ? C1 C2 1.383(3) . ? C2 C3 1.379(3) . ? C3 C4 1.402(3) . ? C4 C20 1.383(3) . ? C4 C5 1.521(3) . ? C5 C6 1.525(3) . ? C5 C7 1.537(3) . ? C5 C8 1.535(3) . ? C8 C9 1.504(3) . ? C9 C10 1.514(3) . ? C10 C11 1.526(3) . ? C11 C14 1.509(3) . ? C11 C13 1.540(3) . ? C11 C12 1.540(3) . ? C14 C19 1.394(3) . ? C14 C15 1.392(3) . ? C15 C16 1.370(3) . ? C16 C17 1.389(3) . ? C17 C18 1.380(3) . ? C18 C19 1.386(3) . ? C20 C21 1.384(3) . ? C22 C23 1.370(4) . ? C23 C24 1.387(3) . ? C24 C25 1.386(4) . ? C24 C27 1.470(4) . ? C25 C26 1.380(4) . ? C27 C28 1.300(4) . ? C28 C29 1.466(4) . ? C29 C30 1.366(4) . ? C29 C33 1.373(3) . ? C30 C31 1.372(4) . ? C32 C33 1.377(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 O1 C9 119.14(15) . . ? C20 O2 C9 118.40(15) . . ? C26 N1 C22 116.5(3) . . ? C32 N2 C31 115.3(3) . . ? O4 C1 C21 123.2(2) . . ? O4 C1 C2 117.4(2) . . ? C21 C1 C2 119.4(2) . . ? C3 C2 C1 119.2(2) . . ? C2 C3 C4 123.0(2) . . ? C20 C4 C3 115.8(2) . . ? C20 C4 C5 122.68(18) . . ? C3 C4 C5 121.5(2) . . ? C4 C5 C6 109.70(19) . . ? C4 C5 C7 111.97(18) . . ? C6 C5 C7 109.0(2) . . ? C4 C5 C8 107.99(18) . . ? C6 C5 C8 107.54(19) . . ? C7 C5 C8 110.51(19) . . ? C9 C8 C5 116.31(18) . . ? O2 C9 O1 108.53(16) . . ? O2 C9 C8 111.23(17) . . ? O1 C9 C8 107.33(16) . . ? O2 C9 C10 107.97(16) . . ? O1 C9 C10 110.76(17) . . ? C8 C9 C10 111.01(18) . . ? C11 C10 C9 116.40(18) . . ? C14 C11 C10 108.80(17) . . ? C14 C11 C13 111.17(19) . . ? C10 C11 C13 106.65(19) . . ? C14 C11 C12 109.81(19) . . ? C10 C11 C12 111.58(19) . . ? C13 C11 C12 108.81(19) . . ? C19 C14 C15 115.5(2) . . ? C19 C14 C11 121.8(2) . . ? C15 C14 C11 122.66(18) . . ? C16 C15 C14 123.8(2) . . ? C15 C16 C17 119.4(2) . . ? O3 C17 C18 119.7(2) . . ? O3 C17 C16 121.5(2) . . ? C18 C17 C16 118.8(2) . . ? C17 C18 C19 120.8(2) . . ? C14 C19 O1 123.34(19) . . ? C14 C19 C18 121.8(2) . . ? O1 C19 C18 114.87(18) . . ? O2 C20 C21 114.46(19) . . ? O2 C20 C4 123.10(19) . . ? C21 C20 C4 122.42(19) . . ? C20 C21 C1 120.1(2) . . ? N1 C22 C23 123.9(3) . . ? C24 C23 C22 119.5(3) . . ? C25 C24 C23 116.5(3) . . ? C25 C24 C27 119.9(2) . . ? C23 C24 C27 123.5(3) . . ? C24 C25 C26 119.8(3) . . ? N1 C26 C25 123.7(3) . . ? C28 C27 C24 126.5(3) . . ? C27 C28 C29 126.5(3) . . ? C30 C29 C33 116.2(3) . . ? C30 C29 C28 119.8(3) . . ? C33 C29 C28 124.0(3) . . ? C29 C30 C31 120.3(3) . . ? N2 C31 C30 124.3(3) . . ? N2 C32 C33 124.1(3) . . ? C29 C33 C32 119.7(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 O4 H4A N1 0.82 1.92 2.726(3) 169.1 2_545 _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.881 _refine_diff_density_max 0.269 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.043