data_k0446 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 N2 O4' _chemical_formula_sum 'C30 H28 N2 O4' _chemical_formula_weight 480.54 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2775(7) _cell_length_b 10.3554(8) _cell_length_c 13.6763(8) _cell_angle_alpha 85.718(4) _cell_angle_beta 73.325(4) _cell_angle_gamma 83.745(4) _cell_volume 1249.87(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 5038 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'needle' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.085 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 1.007 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11660 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.1039 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5605 _reflns_number_gt 2892 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Collect (Nonius BV, 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN' _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXTL V6.12(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.12' _computing_publication_material 'SHELXTL V6.12' _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^)+(0.0993P)^2^] 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 ? _refine_ls_extinction_coef none _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5605 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1462 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.2010 _refine_ls_wR_factor_gt 0.1580 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8495(2) 0.4638(2) -0.02367(15) 0.0462(6) Uani 1 1 d . . . H1O H 0.820(4) 0.512(3) 0.040(3) 0.070(11) Uiso 1 1 d . . . O2 O 0.7362(2) 0.2108(2) 0.39843(15) 0.0459(6) Uani 1 1 d . . . H2O H 0.742(4) 0.301(4) 0.379(3) 0.074(12) Uiso 1 1 d . . . O3 O 0.4879(2) 0.83698(18) 0.32307(13) 0.0390(5) Uani 1 1 d . . . O4 O 1.0620(2) 0.61953(18) 0.35441(13) 0.0341(5) Uani 1 1 d . . . N1 N 0.7059(2) 0.5402(2) 0.15839(16) 0.0294(5) Uani 1 1 d . . . N2 N 0.8236(2) 0.4319(2) 0.31146(15) 0.0281(5) Uani 1 1 d . . . C1 C 0.6890(3) 0.6213(2) 0.2449(2) 0.0305(6) Uani 1 1 d . . . H1A H 0.5874 0.6156 0.2952 0.037 Uiso 1 1 calc R . . C2 C 0.5997(3) 0.4707(2) 0.15919(19) 0.0285(6) Uani 1 1 d . . . H2A H 0.5137 0.4700 0.2172 0.034 Uiso 1 1 calc R . . C3 C 0.6077(3) 0.3927(2) 0.07331(18) 0.0273(6) Uani 1 1 d . . . C4 C 0.4895(3) 0.3187(3) 0.0762(2) 0.0338(7) Uani 1 1 d . . . H4A H 0.4061 0.3170 0.1358 0.041 Uiso 1 1 calc R . . C5 C 0.4911(3) 0.2477(3) -0.0059(2) 0.0367(7) Uani 1 1 d . . . H5A H 0.4102 0.1970 -0.0026 0.044 Uiso 1 1 calc R . . C6 C 0.6125(3) 0.2515(3) -0.0930(2) 0.0371(7) Uani 1 1 d . . . H6A H 0.6138 0.2041 -0.1501 0.044 Uiso 1 1 calc R . . C7 C 0.7304(3) 0.3227(3) -0.0977(2) 0.0377(7) Uani 1 1 d . . . H7A H 0.8130 0.3234 -0.1578 0.045 Uiso 1 1 calc R . . C8 C 0.7304(3) 0.3940(3) -0.01540(19) 0.0309(6) Uani 1 1 d . . . C9 C 0.7082(3) 0.7628(3) 0.2008(2) 0.0340(7) Uani 1 1 d . . . C10 C 0.8307(3) 0.7817(3) 0.11665(18) 0.0321(7) Uani 1 1 d . . . H10A H 0.9022 0.7108 0.0908 0.039 Uiso 1 1 calc R . . C11 C 0.8484(4) 0.9067(3) 0.0698(2) 0.0475(8) Uani 1 1 d . . . H11A H 0.9306 0.9205 0.0111 0.057 Uiso 1 1 calc R . . C12 C 0.7439(4) 1.0104(3) 0.1101(2) 0.0501(9) Uani 1 1 d . . . H12A H 0.7558 1.0952 0.0790 0.060 Uiso 1 1 calc R . . C13 C 0.6237(4) 0.9905(3) 0.1947(2) 0.0436(8) Uani 1 1 d . . . H13A H 0.5534 1.0616 0.2220 0.052 Uiso 1 1 calc R . . C14 C 0.6051(3) 0.8654(3) 0.2404(2) 0.0383(7) Uani 1 1 d . . . C15 C 0.3961(4) 0.9457(3) 0.3758(2) 0.0583(10) Uani 1 1 d . . . H15A H 0.3223 0.9139 0.4371 0.087 Uiso 1 1 calc R . . H15B H 0.3430 0.9953 0.3306 0.087 Uiso 1 1 calc R . . H15C H 0.4607 1.0019 0.3954 0.087 Uiso 1 1 calc R . . C16 C 0.8153(3) 0.5741(2) 0.29567(18) 0.0267(6) Uani 1 1 d . . . H16A H 0.9137 0.5975 0.2480 0.032 Uiso 1 1 calc R . . C17 C 0.9380(3) 0.3679(3) 0.25250(19) 0.0297(6) Uani 1 1 d . . . H17A H 1.0099 0.4145 0.2027 0.036 Uiso 1 1 calc R . . C18 C 0.9615(3) 0.2266(3) 0.25923(19) 0.0313(6) Uani 1 1 d . . . C19 C 1.0876(3) 0.1617(3) 0.1930(2) 0.0400(7) Uani 1 1 d . . . H19A H 1.1564 0.2106 0.1428 0.048 Uiso 1 1 calc R . . C20 C 1.1139(4) 0.0287(3) 0.1989(2) 0.0496(8) Uani 1 1 d . . . H20A H 1.1999 -0.0142 0.1533 0.059 Uiso 1 1 calc R . . C21 C 1.0129(4) -0.0422(3) 0.2727(2) 0.0477(8) Uani 1 1 d . . . H21A H 1.0309 -0.1342 0.2773 0.057 Uiso 1 1 calc R . . C22 C 0.8882(4) 0.0178(3) 0.3388(2) 0.0462(8) Uani 1 1 d . . . H22A H 0.8208 -0.0325 0.3888 0.055 Uiso 1 1 calc R . . C23 C 0.8598(3) 0.1532(3) 0.3326(2) 0.0343(7) Uani 1 1 d . . . C24 C 0.7970(3) 0.6324(2) 0.39799(19) 0.0282(6) Uani 1 1 d . . . C25 C 0.6579(3) 0.6615(3) 0.4680(2) 0.0376(7) Uani 1 1 d . . . H25A H 0.5682 0.6491 0.4509 0.045 Uiso 1 1 calc R . . C26 C 0.6470(4) 0.7086(3) 0.5626(2) 0.0439(8) Uani 1 1 d . . . H26A H 0.5507 0.7286 0.6094 0.053 Uiso 1 1 calc R . . C27 C 0.7762(3) 0.7260(3) 0.5883(2) 0.0428(8) Uani 1 1 d . . . H27A H 0.7688 0.7580 0.6531 0.051 Uiso 1 1 calc R . . C28 C 0.9170(3) 0.6975(3) 0.5206(2) 0.0372(7) Uani 1 1 d . . . H28A H 1.0060 0.7095 0.5387 0.045 Uiso 1 1 calc R . . C29 C 0.9270(3) 0.6509(3) 0.42568(19) 0.0305(6) Uani 1 1 d . . . C30 C 1.1970(3) 0.6350(3) 0.3809(2) 0.0449(8) Uani 1 1 d . . . H30A H 1.2851 0.6093 0.3242 0.067 Uiso 1 1 calc R . . H30B H 1.1999 0.5800 0.4420 0.067 Uiso 1 1 calc R . . H30C H 1.1987 0.7262 0.3949 0.067 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 0.0387(12) 0.0613(15) 0.0383(11) -0.0081(10) -0.0024(10) -0.0221(11) O2 0.0439(13) 0.0361(13) 0.0484(12) 0.0029(10) 0.0007(10) -0.0035(10) O3 0.0418(12) 0.0321(11) 0.0374(10) -0.0036(9) -0.0025(9) -0.0009(9) O4 0.0271(10) 0.0454(12) 0.0315(10) -0.0026(9) -0.0103(8) -0.0049(9) N1 0.0336(13) 0.0256(12) 0.0316(11) -0.0008(9) -0.0128(10) -0.0042(10) N2 0.0300(12) 0.0277(12) 0.0285(11) -0.0038(9) -0.0112(10) -0.0013(10) C1 0.0339(15) 0.0275(14) 0.0338(13) -0.0058(11) -0.0149(12) -0.0002(12) C2 0.0299(14) 0.0257(14) 0.0294(13) 0.0000(11) -0.0084(11) -0.0014(11) C3 0.0304(14) 0.0257(14) 0.0278(13) -0.0028(11) -0.0115(11) -0.0016(11) C4 0.0350(16) 0.0347(16) 0.0335(14) -0.0027(12) -0.0110(12) -0.0065(13) C5 0.0374(16) 0.0350(16) 0.0433(16) -0.0044(13) -0.0181(14) -0.0078(13) C6 0.0369(16) 0.0383(16) 0.0390(15) -0.0138(13) -0.0157(13) 0.0053(13) C7 0.0359(16) 0.0450(18) 0.0328(14) -0.0068(13) -0.0105(13) -0.0006(14) C8 0.0301(15) 0.0333(15) 0.0311(14) 0.0010(12) -0.0108(12) -0.0062(12) C9 0.0362(16) 0.0376(16) 0.0341(14) -0.0055(12) -0.0188(13) -0.0020(13) C10 0.0330(15) 0.0365(16) 0.0277(13) 0.0012(12) -0.0075(12) -0.0118(13) C11 0.0484(19) 0.052(2) 0.0436(17) 0.0043(15) -0.0120(15) -0.0158(17) C12 0.059(2) 0.0417(19) 0.0530(19) 0.0087(15) -0.0215(17) -0.0119(17) C13 0.058(2) 0.0306(16) 0.0501(18) 0.0111(13) -0.0266(16) -0.0138(14) C14 0.0378(16) 0.0424(18) 0.0369(15) -0.0003(13) -0.0129(14) -0.0087(14) C15 0.069(2) 0.0421(19) 0.053(2) -0.0112(16) -0.0020(18) 0.0059(17) C16 0.0294(14) 0.0235(14) 0.0290(13) -0.0034(11) -0.0109(11) -0.0020(11) C17 0.0336(15) 0.0292(15) 0.0278(13) -0.0033(11) -0.0103(12) -0.0035(12) C18 0.0326(15) 0.0315(15) 0.0317(13) -0.0056(11) -0.0125(12) 0.0009(12) C19 0.0423(18) 0.0385(17) 0.0357(15) -0.0060(13) -0.0068(13) 0.0025(14) C20 0.057(2) 0.0418(18) 0.0468(18) -0.0095(15) -0.0136(16) 0.0135(16) C21 0.072(2) 0.0290(16) 0.0473(17) -0.0035(14) -0.0297(17) 0.0080(16) C22 0.063(2) 0.0344(17) 0.0426(17) 0.0012(14) -0.0178(16) -0.0064(15) C23 0.0381(16) 0.0333(16) 0.0322(14) -0.0018(12) -0.0119(13) -0.0010(13) C24 0.0309(15) 0.0236(13) 0.0311(13) -0.0033(11) -0.0107(12) 0.0007(11) C25 0.0342(16) 0.0409(17) 0.0386(15) -0.0092(13) -0.0126(13) 0.0045(13) C26 0.0414(18) 0.052(2) 0.0352(15) -0.0158(14) -0.0078(14) 0.0096(15) C27 0.0502(19) 0.0436(18) 0.0360(15) -0.0132(13) -0.0156(14) 0.0061(15) C28 0.0418(17) 0.0358(16) 0.0386(15) -0.0054(13) -0.0186(13) -0.0011(13) C29 0.0333(15) 0.0274(14) 0.0315(14) -0.0015(11) -0.0107(12) -0.0017(12) C30 0.0314(16) 0.060(2) 0.0437(16) 0.0016(15) -0.0120(14) -0.0065(15) _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 C8 1.358(3) . ? O2 C23 1.349(3) . ? O3 C14 1.365(3) . ? O3 C15 1.439(3) . ? O4 C29 1.372(3) . ? O4 C30 1.428(3) . ? N1 C2 1.279(3) . ? N1 C1 1.464(3) . ? N2 C17 1.285(3) . ? N2 C16 1.468(3) . ? C1 C16 1.544(4) . ? C1 C9 1.551(4) . ? C2 C3 1.455(4) . ? C3 C4 1.395(4) . ? C3 C8 1.406(3) . ? C4 C5 1.383(4) . ? C5 C6 1.386(4) . ? C6 C7 1.367(4) . ? C7 C8 1.392(4) . ? C9 C14 1.380(4) . ? C9 C10 1.385(4) . ? C10 C11 1.405(4) . ? C11 C12 1.397(4) . ? C12 C13 1.378(4) . ? C13 C14 1.402(4) . ? C16 C24 1.523(4) . ? C17 C18 1.455(4) . ? C18 C19 1.397(4) . ? C18 C23 1.405(4) . ? C19 C20 1.373(4) . ? C20 C21 1.390(4) . ? C21 C22 1.366(4) . ? C22 C23 1.399(4) . ? C24 C25 1.387(4) . ? C24 C29 1.399(4) . ? C25 C26 1.390(4) . ? C26 C27 1.375(4) . ? C27 C28 1.383(4) . ? C28 C29 1.393(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 C14 O3 C15 116.6(2) . . ? C29 O4 C30 117.3(2) . . ? C2 N1 C1 119.2(2) . . ? C17 N2 C16 116.2(2) . . ? N1 C1 C16 108.3(2) . . ? N1 C1 C9 106.9(2) . . ? C16 C1 C9 110.0(2) . . ? N1 C2 C3 121.5(2) . . ? C4 C3 C8 118.6(2) . . ? C4 C3 C2 120.1(2) . . ? C8 C3 C2 121.2(2) . . ? C5 C4 C3 121.4(2) . . ? C4 C5 C6 119.0(3) . . ? C7 C6 C5 120.9(3) . . ? C6 C7 C8 120.7(3) . . ? O1 C8 C7 118.7(2) . . ? O1 C8 C3 121.9(2) . . ? C7 C8 C3 119.4(2) . . ? C14 C9 C10 120.9(3) . . ? C14 C9 C1 122.0(2) . . ? C10 C9 C1 117.1(2) . . ? C9 C10 C11 119.5(3) . . ? C12 C11 C10 119.5(3) . . ? C13 C12 C11 120.5(3) . . ? C12 C13 C14 120.0(3) . . ? O3 C14 C9 116.6(3) . . ? O3 C14 C13 123.7(3) . . ? C9 C14 C13 119.7(3) . . ? N2 C16 C24 108.02(19) . . ? N2 C16 C1 109.9(2) . . ? C24 C16 C1 114.6(2) . . ? N2 C17 C18 122.4(2) . . ? C19 C18 C23 118.8(3) . . ? C19 C18 C17 120.2(2) . . ? C23 C18 C17 121.0(2) . . ? C20 C19 C18 121.3(3) . . ? C19 C20 C21 119.0(3) . . ? C22 C21 C20 121.4(3) . . ? C21 C22 C23 120.0(3) . . ? O2 C23 C22 119.2(2) . . ? O2 C23 C18 121.3(2) . . ? C22 C23 C18 119.5(3) . . ? C25 C24 C29 118.0(2) . . ? C25 C24 C16 123.3(2) . . ? C29 C24 C16 118.6(2) . . ? C24 C25 C26 121.3(3) . . ? C27 C26 C25 119.7(3) . . ? C26 C27 C28 120.5(3) . . ? C27 C28 C29 119.4(3) . . ? O4 C29 C28 123.1(3) . . ? O4 C29 C24 115.9(2) . . ? C28 C29 C24 121.0(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 O1 H1O N1 0.99(4) 1.69(3) 2.600(3) 152(3) . O2 H2O N2 0.95(4) 1.71(4) 2.600(3) 155(3) . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.612 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.059