# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email P.B.WYATT@QMUL.AC.UK _publ_contact_author_name 'Dr Peter Brian Wyatt' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; Department of Chemistry Queen Mary, University of London Mile End Road London E1 4NS UNITED KINGDOM ; _publ_section_title ; Generation of strong, homochiral bases by electrochemical reduction of phenazine derivatives ; loop_ _publ_author_name 'Peter Brian Wyatt' 'A Mateo Alonso' 'Helen J. Groombridge' 'Roberto Horcajada' 'Reshma Mandalia' ; M.Motevalli ; 'J. Utley' data_ama-1534 _database_code_depnum_ccdc_archive 'CCDC 223727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N2 O4' _chemical_formula_weight 408.48 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.436(11) _cell_length_b 17.1160(12) _cell_length_c 8.713(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.712(14) _cell_angle_gamma 90.00 _cell_volume 1068(2) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.348 _cell_measurement_theta_max 11.956 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 160(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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 5 _diffrn_reflns_number 3892 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2938 _reflns_number_gt 2498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0436P)^2^+0.1101P] 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 0.016(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 0.7(10) _refine_ls_number_reflns 2938 _refine_ls_number_parameters 272 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.9090(2) 0.58989(9) 0.60915(17) 0.0290(4) Uani 1 1 d . . . O2 O 1.2364(2) 0.68540(9) 0.96827(17) 0.0249(4) Uani 1 1 d . . . N1 N 1.0892(3) 0.47195(11) 0.8264(2) 0.0241(4) Uani 1 1 d . . . C6 C 1.1176(3) 0.41253(12) 1.0835(3) 0.0223(5) Uani 1 1 d . . . C12 C 0.9407(3) 0.50938(13) 0.8485(2) 0.0227(5) Uani 1 1 d . . . N2 N 0.9611(3) 0.44483(10) 1.0992(2) 0.0250(5) Uani 1 1 d . . . O3 O 1.3125(2) 0.57490(8) 1.32872(17) 0.0264(4) Uani 1 1 d . . . O4 O 1.1851(2) 0.35726(9) 1.35202(18) 0.0291(4) Uani 1 1 d . . . C1 C 1.2296(3) 0.36505(13) 1.2108(3) 0.0243(5) Uani 1 1 d . . . C10 C 0.6889(3) 0.60178(14) 0.7556(3) 0.0304(6) Uani 1 1 d . . . H10 H 0.6255 0.6393 0.6799 0.036 Uiso 1 1 calc R . . C21 C 1.3630(3) 0.61783(13) 1.2054(3) 0.0248(5) Uani 1 1 d . . . H21 H 1.4034 0.5800 1.1339 0.030 Uiso 1 1 calc R . . C2 C 1.3744(4) 0.32407(13) 1.1867(3) 0.0276(6) Uani 1 1 d . . . H2 H 1.4433 0.2904 1.2683 0.033 Uiso 1 1 calc R . . C11 C 0.8472(3) 0.56864(13) 0.7377(3) 0.0246(5) Uani 1 1 d . . . C7 C 0.8695(3) 0.49323(13) 0.9819(3) 0.0239(5) Uani 1 1 d . . . C5 C 1.1782(3) 0.42200(13) 0.9426(3) 0.0234(5) Uani 1 1 d . . . C16 C 1.1897(3) 0.66035(13) 1.1093(3) 0.0240(5) Uani 1 1 d . . . H16 H 1.0842 0.6222 1.0787 0.029 Uiso 1 1 calc R . . C8 C 0.7039(3) 0.52959(14) 0.9955(3) 0.0302(6) Uani 1 1 d . . . H8 H 0.6548 0.5172 1.0825 0.036 Uiso 1 1 calc R . . C3 C 1.4258(4) 0.33019(14) 1.0422(3) 0.0321(6) Uani 1 1 d . . . H3 H 1.5267 0.2997 1.0277 0.039 Uiso 1 1 calc R . . C4 C 1.3330(4) 0.37909(13) 0.9234(3) 0.0297(6) Uani 1 1 d . . . H4 H 1.3721 0.3843 0.8288 0.036 Uiso 1 1 calc R . . C20 C 1.5219(4) 0.67452(14) 1.2724(3) 0.0312(6) Uani 1 1 d . . . H20A H 1.5631 0.6977 1.1836 0.037 Uiso 1 1 calc R . . H20B H 1.6289 0.6457 1.3416 0.037 Uiso 1 1 calc R . . C17 C 1.1330(4) 0.72708(15) 1.2020(3) 0.0315(6) Uani 1 1 d . . . H17A H 1.0888 0.7052 1.2906 0.038 Uiso 1 1 calc R . . H17B H 1.0279 0.7560 1.1307 0.038 Uiso 1 1 calc R . . C14 C 1.1110(4) 0.70599(13) 0.6869(3) 0.0297(6) Uani 1 1 d . . . H14A H 1.0127 0.7350 0.6081 0.036 Uiso 1 1 calc R . . H14B H 1.2333 0.7259 0.6793 0.036 Uiso 1 1 calc R . . C18 C 1.2932(4) 0.78353(14) 1.2698(3) 0.0377(6) Uani 1 1 d . . . H18A H 1.2537 0.8228 1.3374 0.045 Uiso 1 1 calc R . . H18B H 1.3259 0.8114 1.1814 0.045 Uiso 1 1 calc R . . C23 C 1.3681(4) 0.46521(13) 1.5069(3) 0.0275(5) Uani 1 1 d . . . H23A H 1.4593 0.4232 1.5498 0.033 Uiso 1 1 calc R . . H23B H 1.3637 0.4996 1.5972 0.033 Uiso 1 1 calc R . . C9 C 0.6155(3) 0.58188(16) 0.8846(3) 0.0321(6) Uani 1 1 d . . . H9 H 0.5031 0.6056 0.8931 0.039 Uiso 1 1 calc R . . C13 C 1.0965(3) 0.62052(14) 0.6406(3) 0.0285(5) Uani 1 1 d . . . H13A H 1.1410 0.6137 0.5441 0.034 Uiso 1 1 calc R . . H13B H 1.1797 0.5898 0.7276 0.034 Uiso 1 1 calc R . . C24 C 1.1787(4) 0.42847(14) 1.4430(3) 0.0296(6) Uani 1 1 d . . . H24A H 1.1264 0.4159 1.5332 0.036 Uiso 1 1 calc R . . H24B H 1.0941 0.4666 1.3737 0.036 Uiso 1 1 calc R . . C19 C 1.4638(4) 0.73966(15) 1.3686(3) 0.0397(7) Uani 1 1 d . . . H19A H 1.4350 0.7170 1.4638 0.048 Uiso 1 1 calc R . . H19B H 1.5688 0.7767 1.4056 0.048 Uiso 1 1 calc R . . C15 C 1.0923(4) 0.72424(14) 0.8523(3) 0.0274(5) Uani 1 1 d . . . H15A H 1.1017 0.7813 0.8709 0.033 Uiso 1 1 calc R . . H15B H 0.9687 0.7067 0.8613 0.033 Uiso 1 1 calc R . . C22 C 1.4407(3) 0.51277(13) 1.3893(3) 0.0262(5) Uani 1 1 d . . . H22A H 1.5652 0.5345 1.4430 0.031 Uiso 1 1 calc R . . H22B H 1.4533 0.4790 1.3005 0.031 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 0.0329(9) 0.0336(9) 0.0175(8) 0.0031(7) 0.0018(7) 0.0020(8) O2 0.0269(8) 0.0281(9) 0.0188(8) 0.0031(6) 0.0046(7) 0.0041(8) N1 0.0281(10) 0.0225(9) 0.0209(10) -0.0023(8) 0.0053(9) 0.0011(9) C6 0.0268(12) 0.0145(11) 0.0245(12) -0.0021(9) 0.0048(10) -0.0013(11) C12 0.0249(11) 0.0202(11) 0.0198(11) -0.0045(9) 0.0003(10) -0.0015(11) N2 0.0266(11) 0.0240(11) 0.0240(10) -0.0006(8) 0.0060(9) -0.0032(9) O3 0.0334(9) 0.0213(8) 0.0264(9) 0.0054(7) 0.0112(8) 0.0044(8) O4 0.0432(10) 0.0208(8) 0.0233(8) 0.0013(6) 0.0092(8) -0.0031(8) C1 0.0328(14) 0.0174(11) 0.0213(11) -0.0012(9) 0.0051(11) -0.0052(11) C10 0.0282(13) 0.0307(14) 0.0259(12) -0.0001(10) -0.0036(11) 0.0050(12) C21 0.0296(13) 0.0237(12) 0.0225(12) 0.0008(9) 0.0093(11) -0.0004(11) C2 0.0362(14) 0.0162(12) 0.0278(13) 0.0019(9) 0.0041(12) 0.0013(11) C11 0.0277(12) 0.0234(13) 0.0187(11) -0.0015(9) -0.0006(10) 0.0004(11) C7 0.0237(12) 0.0232(11) 0.0228(12) -0.0008(10) 0.0028(10) -0.0029(11) C5 0.0296(12) 0.0180(11) 0.0209(11) -0.0008(9) 0.0040(10) 0.0003(11) C16 0.0267(12) 0.0228(11) 0.0229(11) 0.0006(9) 0.0071(10) -0.0026(11) C8 0.0259(13) 0.0361(15) 0.0287(13) -0.0002(12) 0.0077(11) 0.0012(12) C3 0.0359(15) 0.0257(12) 0.0343(14) -0.0024(11) 0.0089(12) 0.0069(12) C4 0.0339(14) 0.0310(14) 0.0249(12) -0.0002(10) 0.0091(11) 0.0072(12) C20 0.0294(13) 0.0339(13) 0.0268(13) 0.0084(11) 0.0015(11) -0.0023(12) C17 0.0374(14) 0.0281(12) 0.0311(13) 0.0025(11) 0.0133(12) 0.0068(12) C14 0.0368(14) 0.0270(12) 0.0237(12) 0.0082(9) 0.0056(11) 0.0060(12) C18 0.0599(18) 0.0236(13) 0.0313(13) -0.0037(11) 0.0151(14) -0.0015(14) C23 0.0378(14) 0.0206(11) 0.0222(11) 0.0026(10) 0.0046(11) 0.0039(12) C9 0.0212(12) 0.0383(14) 0.0343(13) -0.0057(12) 0.0030(11) 0.0071(13) C13 0.0349(13) 0.0302(13) 0.0208(11) 0.0020(10) 0.0082(11) 0.0071(12) C24 0.0399(14) 0.0279(12) 0.0226(12) 0.0029(10) 0.0112(11) 0.0046(12) C19 0.0525(18) 0.0326(14) 0.0286(13) -0.0043(11) 0.0020(13) -0.0139(14) C15 0.0295(13) 0.0241(12) 0.0254(12) -0.0010(10) 0.0019(11) 0.0069(11) C22 0.0294(12) 0.0195(11) 0.0270(12) 0.0002(9) 0.0028(11) 0.0013(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 O1 C11 1.370(3) . ? O1 C13 1.445(3) . ? O2 C15 1.423(3) . ? O2 C16 1.430(3) . ? N1 C12 1.335(3) . ? N1 C5 1.353(3) . ? C6 N2 1.329(3) . ? C6 C5 1.427(4) . ? C6 C1 1.443(3) . ? C12 C7 1.429(4) . ? C12 C11 1.442(3) . ? N2 C7 1.349(3) . ? O3 C22 1.430(3) . ? O3 C21 1.433(3) . ? O4 C1 1.365(3) . ? O4 C24 1.462(3) . ? C1 C2 1.348(4) . ? C10 C11 1.353(4) . ? C10 C9 1.418(4) . ? C10 H10 0.9500 . ? C21 C20 1.518(4) . ? C21 C16 1.519(4) . ? C21 H21 1.0000 . ? C2 C3 1.415(4) . ? C2 H2 0.9500 . ? C7 C8 1.413(4) . ? C5 C4 1.413(4) . ? C16 C17 1.523(3) . ? C16 H16 1.0000 . ? C8 C9 1.350(4) . ? C8 H8 0.9500 . ? C3 C4 1.364(4) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C20 C19 1.526(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C17 C18 1.523(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C14 C13 1.514(3) . ? C14 C15 1.517(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C18 C19 1.524(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C23 C24 1.505(4) . ? C23 C22 1.517(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C9 H9 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C13 117.48(18) . . ? C15 O2 C16 116.0(2) . . ? C12 N1 C5 116.8(2) . . ? N2 C6 C5 122.1(2) . . ? N2 C6 C1 119.6(2) . . ? C5 C6 C1 118.3(2) . . ? N1 C12 C7 121.9(2) . . ? N1 C12 C11 120.6(2) . . ? C7 C12 C11 117.6(2) . . ? C6 N2 C7 117.0(2) . . ? C22 O3 C21 111.95(19) . . ? C1 O4 C24 117.33(17) . . ? C2 C1 O4 119.2(2) . . ? C2 C1 C6 119.5(2) . . ? O4 C1 C6 121.2(2) . . ? C11 C10 C9 121.6(2) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? O3 C21 C20 112.0(2) . . ? O3 C21 C16 107.7(2) . . ? C20 C21 C16 111.2(2) . . ? O3 C21 H21 108.6 . . ? C20 C21 H21 108.6 . . ? C16 C21 H21 108.6 . . ? C1 C2 C3 121.3(2) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C10 C11 O1 118.5(2) . . ? C10 C11 C12 119.6(2) . . ? O1 C11 C12 121.7(2) . . ? N2 C7 C8 118.7(2) . . ? N2 C7 C12 120.9(2) . . ? C8 C7 C12 120.4(2) . . ? N1 C5 C4 119.3(2) . . ? N1 C5 C6 120.8(2) . . ? C4 C5 C6 120.0(2) . . ? O2 C16 C21 104.5(2) . . ? O2 C16 C17 113.4(2) . . ? C21 C16 C17 112.5(2) . . ? O2 C16 H16 108.8 . . ? C21 C16 H16 108.8 . . ? C17 C16 H16 108.8 . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C21 C20 C19 111.8(2) . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C16 C17 C18 112.4(2) . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C13 C14 C15 115.7(2) . . ? C13 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C13 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C17 C18 C19 110.5(2) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C24 C23 C22 116.3(2) . . ? C24 C23 H23A 108.2 . . ? C22 C23 H23A 108.2 . . ? C24 C23 H23B 108.2 . . ? C22 C23 H23B 108.2 . . ? H23A C23 H23B 107.4 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? O1 C13 C14 113.4(2) . . ? O1 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? O1 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? O4 C24 C23 112.6(2) . . ? O4 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? O4 C24 H24B 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C18 C19 C20 111.5(2) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? O2 C15 C14 109.5(2) . . ? O2 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? O2 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? O3 C22 C23 108.9(2) . . ? O3 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? O3 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.159 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.039 data_ama-1376 _database_code_depnum_ccdc_archive 'CCDC 223728' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H31 N2 O7' _chemical_formula_weight 519.56 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.429(7) _cell_length_b 15.650(14) _cell_length_c 9.980(9) _cell_angle_alpha 90.00 _cell_angle_beta 105.40(7) _cell_angle_gamma 90.00 _cell_volume 1269.2(19) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.698 _cell_measurement_theta_max 13.406 _exptl_crystal_description prism _exptl_crystal_colour amber _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 550 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9807 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 160(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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3776 _diffrn_reflns_av_R_equivalents 0.0063 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3408 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0660P)^2^+0.7812P] 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 -0.6(12) _refine_ls_number_reflns 3408 _refine_ls_number_parameters 332 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2929(3) 0.81073(16) 0.8337(3) 0.0166(5) Uani 1 1 d . . . N2 N 0.4288(3) 0.65424(17) 0.8472(3) 0.0199(6) Uani 1 1 d . . . O1 O 0.3952(2) 0.99796(15) 1.0523(2) 0.0261(5) Uani 1 1 d . . . O2 O 0.4494(3) 0.92711(16) 0.8185(3) 0.0304(6) Uani 1 1 d . . . O3 O 0.0290(2) 0.83440(16) 0.9662(3) 0.0268(5) Uani 1 1 d . . . O4 O -0.1825(3) 0.69728(17) 0.8037(3) 0.0384(7) Uani 1 1 d . . . O5 O -0.0850(3) 0.52977(17) 0.5879(3) 0.0330(6) Uani 1 1 d . . . O6 O 0.2155(3) 0.50541(19) 0.3895(3) 0.0331(6) Uani 1 1 d . . . O7 O 0.4845(3) 0.57735(15) 0.6243(2) 0.0246(5) Uani 1 1 d . . . C1 C 0.2471(4) 1.0378(2) 0.9718(4) 0.0361(9) Uani 1 1 d . . . H1A H 0.2482 1.0397 0.8739 0.054 Uiso 1 1 calc R . . H1B H 0.2402 1.0961 1.0057 0.054 Uiso 1 1 calc R . . H1C H 0.1516 1.0048 0.9808 0.054 Uiso 1 1 calc R . . C2 C 0.3909(3) 0.9077(2) 1.0396(3) 0.0211(7) Uani 1 1 d . . . H2 H 0.2920 0.8848 1.0650 0.025 Uiso 1 1 calc R . . C3 C 0.54554(18) 0.86923(13) 1.1342(2) 0.0223(6) Uani 1 1 d G . . C4 C 0.53296(19) 0.79499(14) 1.2071(2) 0.0276(7) Uani 1 1 d G . . H4 H 0.4282 0.7700 1.1994 0.033 Uiso 1 1 calc R . . C5 C 0.6737(2) 0.75730(14) 1.2914(2) 0.0342(8) Uani 1 1 d G . . H5 H 0.6651 0.7066 1.3413 0.041 Uiso 1 1 calc R . . C6 C 0.8270(2) 0.79384(16) 1.3027(2) 0.0308(8) Uani 1 1 d G . . H6 H 0.9231 0.7681 1.3603 0.037 Uiso 1 1 calc R . . C7 C 0.83956(17) 0.86808(15) 1.2298(3) 0.0341(8) Uani 1 1 d G . . H7 H 0.9443 0.8931 1.2375 0.041 Uiso 1 1 calc R . . C8 C 0.6988(2) 0.90577(12) 1.1455(2) 0.0303(8) Uani 1 1 d G . . H8 H 0.7074 0.9565 1.0956 0.036 Uiso 1 1 calc R . . C9 C 0.3817(3) 0.8840(2) 0.8867(3) 0.0200(6) Uani 1 1 d . . . C10 C 0.2438(3) 0.7483(2) 0.9207(3) 0.0184(6) Uani 1 1 d . . . C11 C 0.1201(3) 0.7606(2) 0.9874(3) 0.0201(6) Uani 1 1 d . . . C12 C 0.1013(4) 0.7025(2) 1.0856(3) 0.0249(7) Uani 1 1 d . . . H12 H 0.0218 0.7124 1.1357 0.030 Uiso 1 1 calc R . . C13 C 0.1978(4) 0.6298(2) 1.1115(3) 0.0257(7) Uani 1 1 d . . . H13 H 0.1860 0.5911 1.1816 0.031 Uiso 1 1 calc R . . C14 C 0.3104(4) 0.6123(2) 1.0378(3) 0.0240(7) Uani 1 1 d . . . H14 H 0.3746 0.5617 1.0555 0.029 Uiso 1 1 calc R . . C15 C 0.3291(3) 0.6703(2) 0.9363(3) 0.0183(6) Uani 1 1 d . . . C16 C 0.3879(3) 0.6955(2) 0.7183(3) 0.0164(6) Uani 1 1 d . . . C17 C 0.4133(3) 0.6566(2) 0.5997(3) 0.0200(6) Uani 1 1 d . . . C18 C 0.3661(4) 0.6984(2) 0.4725(3) 0.0236(7) Uani 1 1 d . . . H18 H 0.3829 0.6723 0.3914 0.028 Uiso 1 1 calc R . . C19 C 0.2939(3) 0.7788(2) 0.4649(3) 0.0237(7) Uani 1 1 d . . . H19 H 0.2624 0.8073 0.3778 0.028 Uiso 1 1 calc R . . C20 C 0.2671(3) 0.8180(2) 0.5800(3) 0.0208(7) Uani 1 1 d . . . H20 H 0.2177 0.8729 0.5730 0.025 Uiso 1 1 calc R . . C21 C 0.3137(3) 0.7757(2) 0.7071(3) 0.0177(6) Uani 1 1 d . . . C22 C 0.5017(4) 0.5241(2) 0.5112(4) 0.0252(7) Uani 1 1 d . . . H22A H 0.6065 0.4921 0.5404 0.030 Uiso 1 1 calc R . . H22B H 0.5063 0.5607 0.4314 0.030 Uiso 1 1 calc R . . C23 C 0.3620(4) 0.4623(2) 0.4665(4) 0.0305(8) Uani 1 1 d . . . H23A H 0.3917 0.4173 0.4078 0.037 Uiso 1 1 calc R . . H23B H 0.3412 0.4346 0.5494 0.037 Uiso 1 1 calc R . . C24 C 0.0727(4) 0.4891(3) 0.4358(4) 0.0333(9) Uani 1 1 d . . . H24A H 0.0759 0.4295 0.4700 0.040 Uiso 1 1 calc R . . H24B H -0.0265 0.4955 0.3568 0.040 Uiso 1 1 calc R . . C25 C 0.0617(4) 0.5498(3) 0.5507(4) 0.0320(8) Uani 1 1 d . . . H25A H 0.1584 0.5427 0.6318 0.038 Uiso 1 1 calc R . . H25B H 0.0587 0.6097 0.5181 0.038 Uiso 1 1 calc R . . C26 C -0.0996(4) 0.5732(2) 0.7088(4) 0.0290(7) Uani 1 1 d . . . H26A H 0.0062 0.5690 0.7812 0.035 Uiso 1 1 calc R . . H26B H -0.1847 0.5445 0.7446 0.035 Uiso 1 1 calc R . . C27 C -0.1449(4) 0.6666(2) 0.6830(4) 0.0325(8) Uani 1 1 d . . . H27A H -0.0517 0.6990 0.6652 0.039 Uiso 1 1 calc R . . H27B H -0.2412 0.6728 0.6014 0.039 Uiso 1 1 calc R . . C28 C -0.2236(5) 0.7845(3) 0.8041(6) 0.0551(13) Uani 1 1 d . . . H28A H -0.2874 0.7934 0.8732 0.066 Uiso 1 1 calc R . . H28B H -0.2961 0.7994 0.7117 0.066 Uiso 1 1 calc R . . C29 C -0.0836(6) 0.8432(3) 0.8359(5) 0.0533(11) Uani 1 1 d . . . H29A H -0.0233 0.8359 0.7639 0.064 Uiso 1 1 calc R . . H29B H -0.1268 0.9023 0.8279 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0180(11) 0.0147(14) 0.0179(13) 0.0003(10) 0.0065(9) -0.0008(9) N2 0.0226(12) 0.0193(14) 0.0165(13) -0.0009(11) 0.0029(9) 0.0019(10) O1 0.0244(10) 0.0162(12) 0.0331(13) -0.0086(10) -0.0001(9) 0.0000(8) O2 0.0365(12) 0.0242(13) 0.0346(14) -0.0035(11) 0.0165(10) -0.0124(10) O3 0.0211(10) 0.0242(12) 0.0352(14) -0.0065(11) 0.0075(9) 0.0014(9) O4 0.0301(12) 0.0221(13) 0.0554(18) -0.0044(13) -0.0022(11) 0.0025(10) O5 0.0239(10) 0.0372(15) 0.0380(14) -0.0051(12) 0.0085(10) -0.0088(10) O6 0.0266(11) 0.0446(16) 0.0273(13) 0.0055(12) 0.0056(9) -0.0088(11) O7 0.0282(11) 0.0191(12) 0.0257(12) -0.0070(10) 0.0055(9) 0.0036(9) C1 0.0297(17) 0.028(2) 0.043(2) -0.0106(17) -0.0050(15) 0.0075(14) C2 0.0199(13) 0.0175(16) 0.0261(17) -0.0064(14) 0.0066(12) -0.0028(11) C3 0.0255(14) 0.0226(17) 0.0206(16) -0.0052(14) 0.0092(12) -0.0025(12) C4 0.0264(15) 0.0321(19) 0.0239(16) 0.0004(15) 0.0060(12) -0.0052(13) C5 0.0399(18) 0.035(2) 0.0253(18) 0.0048(17) 0.0038(14) -0.0034(15) C6 0.0308(17) 0.0293(19) 0.0307(19) 0.0010(16) 0.0054(14) 0.0040(13) C7 0.0224(15) 0.033(2) 0.047(2) 0.0021(18) 0.0090(14) 0.0040(14) C8 0.0248(15) 0.0236(18) 0.041(2) 0.0059(16) 0.0068(14) -0.0023(13) C9 0.0172(12) 0.0181(16) 0.0245(16) -0.0028(13) 0.0051(11) 0.0012(11) C10 0.0211(13) 0.0177(16) 0.0141(14) -0.0012(13) 0.0007(11) -0.0045(11) C11 0.0192(13) 0.0211(17) 0.0209(15) -0.0089(13) 0.0071(11) -0.0054(11) C12 0.0281(15) 0.0286(18) 0.0210(16) -0.0083(14) 0.0117(12) -0.0076(13) C13 0.0335(16) 0.0250(19) 0.0197(17) 0.0008(14) 0.0090(13) -0.0108(13) C14 0.0298(15) 0.0185(16) 0.0203(16) 0.0009(14) 0.0010(12) -0.0059(13) C15 0.0183(13) 0.0177(16) 0.0165(15) -0.0025(13) 0.0003(10) -0.0013(11) C16 0.0129(12) 0.0159(15) 0.0205(15) -0.0013(12) 0.0046(11) -0.0019(10) C17 0.0159(13) 0.0197(17) 0.0243(17) -0.0056(13) 0.0054(11) -0.0035(11) C18 0.0253(15) 0.0270(17) 0.0203(16) -0.0051(14) 0.0093(12) -0.0032(12) C19 0.0231(14) 0.0263(17) 0.0210(16) 0.0047(14) 0.0047(12) -0.0016(13) C20 0.0193(14) 0.0208(17) 0.0223(16) 0.0026(13) 0.0055(12) 0.0010(11) C21 0.0153(13) 0.0174(16) 0.0195(15) -0.0015(13) 0.0030(10) -0.0024(11) C22 0.0256(14) 0.0209(18) 0.0317(18) -0.0123(15) 0.0121(12) -0.0011(12) C23 0.0307(16) 0.0245(19) 0.035(2) -0.0075(16) 0.0070(14) -0.0042(13) C24 0.0245(16) 0.046(2) 0.0290(19) 0.0017(17) 0.0057(13) -0.0094(14) C25 0.0249(16) 0.035(2) 0.036(2) 0.0007(17) 0.0065(14) -0.0071(14) C26 0.0271(16) 0.0270(18) 0.0315(19) -0.0012(16) 0.0053(13) -0.0015(13) C27 0.0235(15) 0.0258(19) 0.046(2) 0.0082(17) 0.0046(14) -0.0022(13) C28 0.0306(19) 0.026(2) 0.091(4) -0.006(2) -0.0155(19) 0.0082(16) C29 0.057(2) 0.039(3) 0.057(3) 0.005(2) 0.003(2) 0.0060(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.394(4) . ? N1 C21 1.430(4) . ? N1 C10 1.439(4) . ? N2 C15 1.399(4) . ? N2 C16 1.399(4) . ? O1 C2 1.419(4) . ? O1 C1 1.435(4) . ? O2 C9 1.204(4) . ? O3 C11 1.372(4) . ? O3 C29 1.399(6) . ? O4 C28 1.409(5) . ? O4 C27 1.409(5) . ? O5 C25 1.418(4) . ? O5 C26 1.418(5) . ? O6 C24 1.423(4) . ? O6 C23 1.437(4) . ? O7 C17 1.371(4) . ? O7 C22 1.441(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.516(4) . ? C2 C9 1.552(5) . ? C2 H2 1.0000 . ? C3 C4 1.3900 . ? C3 C8 1.3900 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.3900 . ? C6 H6 0.9500 . ? C7 C8 1.3900 . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 C11 1.392(4) . ? C10 C15 1.403(5) . ? C11 C12 1.376(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9500 . ? C13 C14 1.373(5) . ? C13 H13 0.9500 . ? C14 C15 1.400(5) . ? C14 H14 0.9500 . ? C16 C21 1.393(4) . ? C16 C17 1.397(4) . ? C17 C18 1.389(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9500 . ? C19 C20 1.373(5) . ? C19 H19 0.9500 . ? C20 C21 1.392(5) . ? C20 H20 0.9500 . ? C22 C23 1.497(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.511(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.516(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.462(7) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C21 118.1(2) . . ? C9 N1 C10 122.7(2) . . ? C21 N1 C10 113.3(2) . . ? C15 N2 C16 117.3(2) . . ? C2 O1 C1 112.6(2) . . ? C11 O3 C29 116.1(3) . . ? C28 O4 C27 116.3(4) . . ? C25 O5 C26 113.3(3) . . ? C24 O6 C23 115.0(3) . . ? C17 O7 C22 120.9(3) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 110.0(2) . . ? O1 C2 C9 108.6(3) . . ? C3 C2 C9 109.1(2) . . ? O1 C2 H2 109.7 . . ? C3 C2 H2 109.7 . . ? C9 C2 H2 109.7 . . ? C4 C3 C8 120.0 . . ? C4 C3 C2 119.03(17) . . ? C8 C3 C2 120.95(17) . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.0 . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? O2 C9 N1 122.3(3) . . ? O2 C9 C2 120.9(3) . . ? N1 C9 C2 116.8(3) . . ? C11 C10 C15 119.6(3) . . ? C11 C10 N1 124.5(3) . . ? C15 C10 N1 115.9(3) . . ? O3 C11 C12 120.0(3) . . ? O3 C11 C10 120.2(3) . . ? C12 C11 C10 119.5(3) . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? N2 C15 C14 123.0(3) . . ? N2 C15 C10 117.5(3) . . ? C14 C15 C10 119.4(3) . . ? C21 C16 C17 119.4(3) . . ? C21 C16 N2 119.1(3) . . ? C17 C16 N2 121.5(3) . . ? O7 C17 C18 126.5(3) . . ? O7 C17 C16 113.6(3) . . ? C18 C17 C16 119.8(3) . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C20 C19 C18 121.7(3) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C21 118.7(3) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C20 C21 C16 120.9(3) . . ? C20 C21 N1 123.5(3) . . ? C16 C21 N1 115.6(3) . . ? O7 C22 C23 111.9(3) . . ? O7 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? O7 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? O6 C23 C22 110.6(3) . . ? O6 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? O6 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? O6 C24 C25 111.2(3) . . ? O6 C24 H24A 109.4 . . ? C25 C24 H24A 109.4 . . ? O6 C24 H24B 109.4 . . ? C25 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? O5 C25 C24 107.0(3) . . ? O5 C25 H25A 110.3 . . ? C24 C25 H25A 110.3 . . ? O5 C25 H25B 110.3 . . ? C24 C25 H25B 110.3 . . ? H25A C25 H25B 108.6 . . ? O5 C26 C27 113.1(3) . . ? O5 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? O5 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? O4 C27 C26 106.7(3) . . ? O4 C27 H27A 110.4 . . ? C26 C27 H27A 110.4 . . ? O4 C27 H27B 110.4 . . ? C26 C27 H27B 110.4 . . ? H27A C27 H27B 108.6 . . ? O4 C28 C29 115.1(3) . . ? O4 C28 H28A 108.5 . . ? C29 C28 H28A 108.5 . . ? O4 C28 H28B 108.5 . . ? C29 C28 H28B 108.5 . . ? H28A C28 H28B 107.5 . . ? O3 C29 C28 116.7(4) . . ? O3 C29 H29A 108.1 . . ? C28 C29 H29A 108.1 . . ? O3 C29 H29B 108.1 . . ? C28 C29 H29B 108.1 . . ? H29A C29 H29B 107.3 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.047 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.055 data_ama-1535 _database_code_depnum_ccdc_archive 'CCDC 223729' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N2 O4' _chemical_formula_weight 408.48 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 Orthrohmbic _symmetry_space_group_name_H-M P212121 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 13.3625(4) _cell_length_b 16.2726(5) _cell_length_c 19.4817(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4236.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'noit measured' _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.96852 _exptl_absorpt_correction_T_max 1.00569 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Crysta (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 7.39 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20608 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.1452 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.09 _reflns_number_total 8918 _reflns_number_gt 4506 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997 COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. (1997)' _computing_publication_material 'WINGX(L.J. 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^)+(0.1164P)^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 SHELXL _refine_ls_extinction_coef 0.0065(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 0.00 _refine_ls_number_reflns 8918 _refine_ls_number_parameters 544 _refine_ls_number_restraints 80 _refine_ls_R_factor_all 0.1842 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2376 _refine_ls_wR_factor_gt 0.1970 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.053 _refine_ls_shift/su_mean 0.002 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 -0.2954(4) -1.3944(4) 0.2308(3) 0.0442(14) Uani 1 1 d . . . C2 C -0.3924(4) -1.3690(4) 0.2215(3) 0.0591(18) Uani 1 1 d . . . H2 H -0.4205 -1.3281 0.2506 0.071 Uiso 1 1 calc R . . C3 C -0.4505(4) -1.4046(5) 0.1678(3) 0.067(2) Uani 1 1 d . . . H3 H -0.5187 -1.3889 0.1633 0.081 Uiso 1 1 calc R . . C4 C -0.4128(4) -1.4590(5) 0.1235(4) 0.0594(19) Uani 1 1 d . . . H4 H -0.4535 -1.4813 0.0881 0.071 Uiso 1 1 calc R . . C5 C -0.3105(4) -1.4834(4) 0.1298(3) 0.0441(14) Uani 1 1 d . . . C6 C -0.2534(4) -1.4562(3) 0.1885(3) 0.0443(15) Uani 1 1 d . . . N1 N -0.1601(3) -1.4844(3) 0.2001(2) 0.0405(11) Uani 1 1 d . . . N2 N -0.2664(3) -1.5268(3) 0.0790(2) 0.0453(12) Uani 1 1 d . . . C7 C -0.1692(4) -1.5457(3) 0.0861(3) 0.0426(15) Uani 1 1 d . . . C8 C -0.1119(4) -1.5780(3) 0.0301(3) 0.0419(13) Uani 1 1 d . . . C9 C -0.0162(5) -1.6018(4) 0.0391(3) 0.0532(16) Uani 1 1 d . . . H9 H 0.0204 -1.6240 0.0016 0.064 Uiso 1 1 calc R . . C10 C 0.0309(4) -1.5935(3) 0.1051(3) 0.0551(17) Uani 1 1 d . . . H10 H 0.0976 -1.6125 0.1109 0.066 Uiso 1 1 calc R . . C11 C -0.0179(4) -1.5591(3) 0.1598(3) 0.0430(15) Uani 1 1 d . . . H11 H 0.0139 -1.5544 0.2033 0.052 Uiso 1 1 calc R . . C12 C -0.1184(4) -1.5304(3) 0.1499(3) 0.0375(13) Uani 1 1 d . . . C1A C -0.0439(4) -0.9102(4) 0.0108(3) 0.0425(14) Uani 1 1 d . . . C2A C 0.0500(4) -0.8869(4) 0.0270(3) 0.0469(14) Uani 1 1 d . . . H2A H 0.0872 -0.8544 -0.0044 0.056 Uiso 1 1 calc R . . C3A C 0.0941(4) -0.9103(3) 0.0908(3) 0.0423(14) Uani 1 1 d . . . H3A H 0.1606 -0.8935 0.1008 0.051 Uiso 1 1 calc R . . C4A C 0.0431(4) -0.9560(3) 0.1374(3) 0.0377(13) Uani 1 1 d . . . H4A H 0.0729 -0.9699 0.1802 0.045 Uiso 1 1 calc R . . C5A C -0.0550(3) -0.9826(3) 0.1214(3) 0.0324(12) Uani 1 1 d . . . C6A C -0.0976(4) -0.9650(3) 0.0556(3) 0.0394(13) Uani 1 1 d . . . N1A N -0.1878(3) -0.9953(3) 0.0361(3) 0.0410(11) Uani 1 1 d . . . N2A N -0.1100(3) -1.0203(3) 0.1700(2) 0.0378(11) Uani 1 1 d . . . C7A C -0.2033(3) -1.0432(3) 0.1521(3) 0.0349(12) Uani 1 1 d . . . C8A C -0.2709(4) -1.0735(3) 0.2035(3) 0.0421(14) Uani 1 1 d . . . C9A C -0.3631(4) -1.1017(4) 0.1840(4) 0.0520(16) Uani 1 1 d . . . H9A H -0.4075 -1.1223 0.2179 0.062 Uiso 1 1 calc R . . C10A C -0.3935(4) -1.1007(3) 0.1148(4) 0.0521(16) Uani 1 1 d . . . H10A H -0.4557 -1.1245 0.1023 0.062 Uiso 1 1 calc R . . C11A C -0.3355(4) -1.0664(3) 0.0663(3) 0.0463(15) Uani 1 1 d . . . H11A H -0.3587 -1.0629 0.0203 0.056 Uiso 1 1 calc R . . C12A C -0.2406(3) -1.0357(3) 0.0836(3) 0.0380(13) Uani 1 1 d . . . O1 O -0.1601(3) -1.5803(2) -0.0315(2) 0.0485(10) Uani 1 1 d D . . C13 C -0.1063(4) -1.5422(3) -0.0881(3) 0.0484(15) Uani 1 1 d D . . H13A H -0.0933 -1.5837 -0.1242 0.058 Uiso 1 1 calc R . . H13B H -0.0410 -1.5213 -0.0716 0.058 Uiso 1 1 calc R . . C14 C -0.1659(4) -1.4727(3) -0.1178(3) 0.0402(13) Uani 1 1 d D . . H14A H -0.2232 -1.4959 -0.1435 0.048 Uiso 1 1 calc R . . H14B H -0.1233 -1.4427 -0.1510 0.048 Uiso 1 1 calc R . . C15 C -0.2054(4) -1.4122(3) -0.0657(3) 0.0378(13) Uani 1 1 d D . . H15A H -0.2405 -1.3669 -0.0896 0.045 Uiso 1 1 calc R . . H15B H -0.2539 -1.4399 -0.0351 0.045 Uiso 1 1 calc R . . O2 O -0.1244(2) -1.3796(2) -0.02582(17) 0.0371(8) Uani 1 1 d D . . O1A O -0.2393(3) -1.0692(2) 0.2697(2) 0.0548(11) Uani 1 1 d D . . C13A C -0.3074(5) -1.0273(5) 0.3158(4) 0.074(2) Uani 1 1 d D . . H13C H -0.3347 -1.0669 0.3497 0.089 Uiso 1 1 calc R . . H13D H -0.3640 -1.0039 0.2895 0.089 Uiso 1 1 calc R . . C14A C -0.2516(6) -0.9589(6) 0.3530(3) 0.081(3) Uani 1 1 d D . . H14C H -0.2991 -0.9291 0.3830 0.098 Uiso 1 1 calc R . . H14D H -0.1995 -0.9836 0.3826 0.098 Uiso 1 1 calc R . . C15A C -0.2031(4) -0.8986(4) 0.3050(3) 0.0602(18) Uani 1 1 d D . . H15C H -0.1756 -0.8518 0.3314 0.072 Uiso 1 1 calc R . . H15D H -0.1471 -0.9256 0.2805 0.072 Uiso 1 1 calc R . . O2A O -0.2750(3) -0.8693(3) 0.2564(2) 0.0565(11) Uani 1 1 d D . . C16 C -0.1569(3) -1.3269(3) 0.0300(3) 0.0330(12) Uani 1 1 d D . . H16 H -0.2163 -1.3525 0.0528 0.040 Uiso 1 1 calc R . . C17 C -0.1856(4) -1.2417(3) 0.0047(3) 0.0457(15) Uani 1 1 d D . . H17A H -0.2145 -1.2099 0.0432 0.055 Uiso 1 1 calc R . . H17B H -0.2375 -1.2468 -0.0313 0.055 Uiso 1 1 calc R . . C18 C -0.0944(5) -1.1950(3) -0.0246(3) 0.0529(16) Uani 1 1 d D . . H18A H -0.0692 -1.2238 -0.0660 0.063 Uiso 1 1 calc R . . H18B H -0.1148 -1.1389 -0.0383 0.063 Uiso 1 1 calc R . . C19 C -0.0107(4) -1.1901(3) 0.0297(3) 0.0442(14) Uani 1 1 d D . . H19A H 0.0486 -1.1624 0.0098 0.053 Uiso 1 1 calc R . . H19B H -0.0340 -1.1573 0.0694 0.053 Uiso 1 1 calc R . . C20 C 0.0178(4) -1.2758(3) 0.0534(3) 0.0403(13) Uani 1 1 d D . . H20A H 0.0462 -1.3069 0.0143 0.048 Uiso 1 1 calc R . . H20B H 0.0701 -1.2717 0.0893 0.048 Uiso 1 1 calc R . . C21 C -0.0712(4) -1.3219(3) 0.0819(3) 0.0355(12) Uani 1 1 d D . . H21 H -0.0498 -1.3789 0.0942 0.043 Uiso 1 1 calc R . . C16A C -0.2341(6) -0.8136(4) 0.2061(4) 0.078(2) Uani 1 1 d DU . . H16A H -0.1645 -0.8313 0.1944 0.093 Uiso 1 1 calc R . . C17A C -0.2317(10) -0.7251(5) 0.2317(7) 0.179(6) Uani 1 1 d DU . . H17C H -0.1984 -0.6895 0.1974 0.215 Uiso 1 1 calc R . . H17D H -0.1935 -0.7219 0.2752 0.215 Uiso 1 1 calc R . . C18A C -0.3404(11) -0.6957(6) 0.2435(6) 0.203(7) Uani 1 1 d DU . . H18C H -0.3392 -0.6369 0.2566 0.243 Uiso 1 1 calc R . . H18D H -0.3694 -0.7269 0.2823 0.243 Uiso 1 1 calc R . . C19A C -0.4093(8) -0.7061(5) 0.1799(5) 0.126(4) Uani 1 1 d DU . . H19C H -0.4790 -0.6914 0.1921 0.151 Uiso 1 1 calc R . . H19D H -0.3868 -0.6692 0.1425 0.151 Uiso 1 1 calc R . . C20A C -0.4048(4) -0.7943(4) 0.1563(3) 0.0513(15) Uani 1 1 d DU . . H20C H -0.4358 -0.8300 0.1916 0.062 Uiso 1 1 calc R . . H20D H -0.4440 -0.8002 0.1134 0.062 Uiso 1 1 calc R . . C21A C -0.2991(4) -0.8226(4) 0.1435(3) 0.0542(16) Uani 1 1 d DU . . H21A H -0.3011 -0.8821 0.1306 0.065 Uiso 1 1 calc R . . O3 O -0.1141(2) -1.2840(2) 0.14093(17) 0.0354(8) Uani 1 1 d D . . C22 C -0.0578(4) -1.2977(3) 0.2018(2) 0.0365(12) Uani 1 1 d D . . H22A H 0.0112 -1.2768 0.1960 0.044 Uiso 1 1 calc R . . H22B H -0.0544 -1.3572 0.2120 0.044 Uiso 1 1 calc R . . C23 C -0.1093(4) -1.2529(3) 0.2597(3) 0.0424(13) Uani 1 1 d D . . H23A H -0.0739 -1.2662 0.3030 0.051 Uiso 1 1 calc R . . H23B H -0.1019 -1.1931 0.2519 0.051 Uiso 1 1 calc R . . C24 C -0.2182(4) -1.2715(3) 0.2692(3) 0.0475(15) Uani 1 1 d D . . H24A H -0.2438 -1.2417 0.3099 0.057 Uiso 1 1 calc R . . H24B H -0.2561 -1.2525 0.2285 0.057 Uiso 1 1 calc R . . O4 O -0.2334(3) -1.3587(2) 0.27833(19) 0.0483(10) Uani 1 1 d D . . O3A O -0.2499(6) -0.7765(4) 0.0868(3) 0.138(3) Uani 1 1 d DU . . C22A C -0.2890(9) -0.8111(7) 0.0220(7) 0.165(5) Uani 1 1 d DU . . H22C H -0.2882 -0.8719 0.0233 0.198 Uiso 1 1 calc R . . H22D H -0.3583 -0.7922 0.0134 0.198 Uiso 1 1 calc R . . C23A C -0.2218(7) -0.7805(5) -0.0302(7) 0.148(5) Uani 1 1 d DU . . H23C H -0.2235 -0.7200 -0.0244 0.177 Uiso 1 1 calc R . . H23D H -0.2572 -0.7915 -0.0739 0.177 Uiso 1 1 calc R . . C24A C -0.1180(5) -0.7984(4) -0.0454(3) 0.0582(17) Uani 1 1 d DU . . H24C H -0.1012 -0.7734 -0.0902 0.070 Uiso 1 1 calc R . . H24D H -0.0759 -0.7713 -0.0102 0.070 Uiso 1 1 calc R . . O4A O -0.0915(3) -0.8839(3) -0.0478(2) 0.0613(12) Uani 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 0.033(3) 0.060(4) 0.039(3) 0.022(3) 0.005(3) -0.005(3) C2 0.041(3) 0.087(5) 0.049(4) 0.020(4) 0.008(3) 0.003(3) C3 0.030(3) 0.116(6) 0.055(4) 0.034(5) 0.002(3) 0.009(4) C4 0.025(3) 0.090(5) 0.063(4) 0.035(4) -0.010(3) -0.017(3) C5 0.039(3) 0.053(4) 0.040(3) 0.020(3) -0.008(3) -0.011(3) C6 0.039(3) 0.049(3) 0.045(3) 0.026(3) -0.006(3) -0.005(3) N1 0.037(2) 0.036(2) 0.048(3) 0.018(2) -0.011(2) -0.004(2) N2 0.042(3) 0.047(3) 0.047(3) 0.014(3) -0.017(2) -0.020(2) C7 0.039(3) 0.032(3) 0.057(4) 0.012(3) -0.023(3) -0.012(3) C8 0.048(3) 0.029(3) 0.049(3) -0.004(3) -0.013(3) -0.010(3) C9 0.060(4) 0.041(3) 0.059(4) -0.015(3) -0.017(3) 0.004(3) C10 0.047(3) 0.038(3) 0.080(5) -0.017(3) -0.031(3) 0.014(3) C11 0.044(3) 0.028(3) 0.057(4) 0.000(3) -0.025(3) 0.000(3) C12 0.034(3) 0.031(3) 0.048(3) 0.010(3) -0.013(3) -0.008(2) C1A 0.049(3) 0.044(3) 0.034(3) -0.007(3) -0.004(3) -0.009(3) C2A 0.041(3) 0.056(4) 0.044(3) -0.015(3) 0.000(3) -0.012(3) C3A 0.022(2) 0.052(3) 0.053(4) -0.010(3) -0.005(3) 0.005(3) C4A 0.031(3) 0.047(3) 0.035(3) -0.006(3) -0.004(2) 0.004(3) C5A 0.024(2) 0.032(3) 0.041(3) -0.010(3) -0.008(2) 0.003(2) C6A 0.043(3) 0.036(3) 0.039(3) -0.013(3) -0.005(3) 0.001(3) N1A 0.036(2) 0.034(2) 0.052(3) -0.020(2) -0.001(2) 0.004(2) N2A 0.025(2) 0.034(2) 0.054(3) -0.005(2) -0.005(2) 0.008(2) C7A 0.029(3) 0.027(3) 0.049(3) -0.003(3) 0.000(3) 0.007(2) C8A 0.034(3) 0.032(3) 0.060(4) 0.005(3) -0.002(3) 0.006(2) C9A 0.032(3) 0.043(4) 0.081(5) 0.004(3) 0.009(3) 0.000(3) C10A 0.034(3) 0.031(3) 0.091(5) -0.010(3) -0.004(3) 0.000(3) C11A 0.033(3) 0.035(3) 0.071(4) -0.002(3) -0.004(3) 0.001(3) C12A 0.024(2) 0.033(3) 0.057(4) -0.015(3) -0.001(3) 0.003(2) O1 0.054(2) 0.047(2) 0.044(2) 0.005(2) -0.018(2) -0.0129(19) C13 0.047(3) 0.042(3) 0.056(4) -0.008(3) -0.007(3) 0.005(3) C14 0.040(3) 0.037(3) 0.043(3) -0.007(3) 0.004(3) -0.004(3) C15 0.043(3) 0.037(3) 0.034(3) 0.001(2) -0.005(2) -0.001(3) O2 0.0407(18) 0.0355(18) 0.0351(19) -0.0108(17) 0.0022(17) -0.0008(16) O1A 0.049(2) 0.047(2) 0.068(3) 0.020(2) 0.010(2) 0.008(2) C13A 0.072(4) 0.094(6) 0.056(4) 0.040(4) 0.033(4) 0.012(5) C14A 0.074(5) 0.144(8) 0.026(3) 0.003(5) 0.007(3) 0.056(5) C15A 0.054(3) 0.079(5) 0.048(4) -0.024(4) -0.023(3) 0.017(4) O2A 0.047(2) 0.059(3) 0.063(3) -0.012(2) -0.023(2) 0.008(2) C16 0.033(3) 0.036(3) 0.029(3) -0.004(2) 0.010(2) -0.003(2) C17 0.050(3) 0.042(3) 0.045(3) -0.002(3) -0.005(3) 0.019(3) C18 0.079(4) 0.032(3) 0.048(4) 0.005(3) -0.003(3) 0.007(3) C19 0.057(3) 0.035(3) 0.041(3) -0.002(3) 0.008(3) -0.016(3) C20 0.042(3) 0.040(3) 0.039(3) -0.001(3) 0.007(2) -0.010(3) C21 0.038(3) 0.029(3) 0.039(3) -0.001(2) 0.008(3) 0.001(2) C16A 0.079(5) 0.041(4) 0.113(6) 0.028(4) -0.036(5) -0.022(4) C17A 0.246(13) 0.049(5) 0.243(13) -0.011(7) -0.187(11) -0.018(7) C18A 0.351(16) 0.091(7) 0.166(9) -0.099(7) -0.170(11) 0.122(9) C19A 0.189(9) 0.082(6) 0.107(7) -0.041(5) -0.090(7) 0.074(6) C20A 0.056(4) 0.053(4) 0.045(3) -0.001(3) -0.010(3) 0.008(3) C21A 0.051(3) 0.043(3) 0.069(4) 0.025(3) -0.004(3) -0.006(3) O3 0.0341(18) 0.0384(19) 0.0336(19) -0.0021(17) 0.0072(16) 0.0090(17) C22 0.041(3) 0.038(3) 0.031(3) 0.002(3) -0.002(2) 0.002(2) C23 0.059(3) 0.042(3) 0.026(3) -0.001(3) -0.001(3) 0.013(3) C24 0.056(3) 0.053(4) 0.033(3) 0.011(3) 0.008(3) 0.018(3) O4 0.046(2) 0.058(2) 0.041(2) 0.020(2) -0.0057(19) 0.007(2) O3A 0.203(8) 0.114(5) 0.097(4) 0.074(4) -0.083(5) -0.066(5) C22A 0.138(9) 0.128(9) 0.229(14) 0.087(10) 0.030(10) 0.008(8) C23A 0.100(6) 0.074(5) 0.269(13) -0.045(8) 0.113(8) -0.037(5) C24A 0.060(4) 0.057(4) 0.057(4) 0.025(3) -0.002(3) -0.018(3) O4A 0.070(3) 0.073(3) 0.041(2) -0.003(2) -0.023(2) -0.020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O4 1.372(7) . ? C1 C2 1.373(8) . ? C1 C6 1.415(8) . ? C2 C3 1.427(9) . ? C3 C4 1.335(10) . ? C4 C5 1.429(8) . ? C5 N2 1.352(7) . ? C5 C6 1.445(8) . ? C6 N1 1.347(6) . ? N1 C12 1.352(7) . ? N2 C7 1.342(7) . ? C7 C8 1.432(8) . ? C7 C12 1.438(7) . ? C8 C9 1.348(8) . ? C8 O1 1.363(6) . ? C9 C10 1.438(8) . ? C10 C11 1.370(8) . ? C11 C12 1.435(7) . ? C1A C2A 1.348(7) . ? C1A O4A 1.376(6) . ? C1A C6A 1.439(8) . ? C2A C3A 1.427(8) . ? C3A C4A 1.358(7) . ? C4A C5A 1.417(7) . ? C5A N2A 1.345(6) . ? C5A C6A 1.431(7) . ? C6A N1A 1.356(7) . ? N1A C12A 1.337(7) . ? N2A C7A 1.348(6) . ? C7A C12A 1.431(7) . ? C7A C8A 1.435(8) . ? C8A O1A 1.359(7) . ? C8A C9A 1.368(8) . ? C9A C10A 1.408(9) . ? C10A C11A 1.343(8) . ? C11A C12A 1.403(7) . ? O1 C13 1.455(6) . ? C13 C14 1.499(7) . ? C14 C15 1.508(7) . ? C15 O2 1.435(6) . ? O2 C16 1.452(6) . ? O1A C13A 1.449(7) . ? C13A C14A 1.524(10) . ? C14A C15A 1.503(9) . ? C15A O2A 1.431(6) . ? O2A C16A 1.443(8) . ? C16 C17 1.520(7) . ? C16 C21 1.529(7) . ? C17 C18 1.546(8) . ? C18 C19 1.542(8) . ? C19 C20 1.518(7) . ? C20 C21 1.512(6) . ? C21 O3 1.426(6) . ? C16A C21A 1.504(8) . ? C16A C17A 1.525(10) . ? C17A C18A 1.547(14) . ? C18A C19A 1.552(10) . ? C19A C20A 1.509(9) . ? C20A C21A 1.505(7) . ? C21A O3A 1.490(8) . ? O3 C22 1.422(6) . ? C22 C23 1.509(7) . ? C23 C24 1.499(7) . ? C24 O4 1.443(6) . ? O3A C22A 1.478(13) . ? C22A C23A 1.445(11) . ? C23A C24A 1.447(9) . ? C24A O4A 1.436(7) . ? 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 O4 C1 C2 122.1(6) . . ? O4 C1 C6 117.0(4) . . ? C2 C1 C6 120.8(6) . . ? C1 C2 C3 119.2(6) . . ? C4 C3 C2 122.6(6) . . ? C3 C4 C5 119.3(6) . . ? N2 C5 C4 119.9(6) . . ? N2 C5 C6 120.7(5) . . ? C4 C5 C6 119.2(6) . . ? N1 C6 C1 120.8(5) . . ? N1 C6 C5 121.1(6) . . ? C1 C6 C5 117.9(5) . . ? C6 N1 C12 116.6(5) . . ? C7 N2 C5 117.8(5) . . ? N2 C7 C8 121.5(5) . . ? N2 C7 C12 120.4(6) . . ? C8 C7 C12 118.0(5) . . ? C9 C8 O1 123.7(6) . . ? C9 C8 C7 121.0(5) . . ? O1 C8 C7 115.4(5) . . ? C8 C9 C10 120.2(6) . . ? C11 C10 C9 121.8(5) . . ? C10 C11 C12 118.3(5) . . ? N1 C12 C11 117.9(5) . . ? N1 C12 C7 121.8(5) . . ? C11 C12 C7 120.1(5) . . ? C2A C1A O4A 122.5(5) . . ? C2A C1A C6A 119.8(5) . . ? O4A C1A C6A 117.7(5) . . ? C1A C2A C3A 120.9(6) . . ? C4A C3A C2A 121.5(5) . . ? C3A C4A C5A 119.0(5) . . ? N2A C5A C4A 119.3(5) . . ? N2A C5A C6A 120.3(4) . . ? C4A C5A C6A 120.3(5) . . ? N1A C6A C5A 122.1(5) . . ? N1A C6A C1A 119.9(5) . . ? C5A C6A C1A 118.0(5) . . ? C12A N1A C6A 117.1(5) . . ? C5A N2A C7A 116.7(4) . . ? N2A C7A C12A 122.7(5) . . ? N2A C7A C8A 119.8(5) . . ? C12A C7A C8A 117.5(4) . . ? O1A C8A C9A 124.0(6) . . ? O1A C8A C7A 116.7(4) . . ? C9A C8A C7A 119.2(6) . . ? C8A C9A C10A 121.4(6) . . ? C11A C10A C9A 120.8(5) . . ? C10A C11A C12A 120.0(6) . . ? N1A C12A C11A 119.1(5) . . ? N1A C12A C7A 120.2(4) . . ? C11A C12A C7A 120.5(5) . . ? C8 O1 C13 115.0(4) . . ? O1 C13 C14 110.6(4) . . ? C13 C14 C15 114.8(5) . . ? O2 C15 C14 109.9(4) . . ? C15 O2 C16 113.5(3) . . ? C8A O1A C13A 114.8(5) . . ? O1A C13A C14A 109.3(5) . . ? C15A C14A C13A 113.1(5) . . ? O2A C15A C14A 109.8(5) . . ? C15A O2A C16A 113.8(5) . . ? O2 C16 C17 111.8(4) . . ? O2 C16 C21 107.5(4) . . ? C17 C16 C21 110.8(4) . . ? C16 C17 C18 111.7(4) . . ? C19 C18 C17 110.1(4) . . ? C20 C19 C18 110.1(4) . . ? C21 C20 C19 111.7(4) . . ? O3 C21 C20 113.4(4) . . ? O3 C21 C16 104.8(4) . . ? C20 C21 C16 111.9(4) . . ? O2A C16A C21A 105.7(5) . . ? O2A C16A C17A 112.2(8) . . ? C21A C16A C17A 111.7(6) . . ? C16A C17A C18A 108.7(7) . . ? C17A C18A C19A 113.9(9) . . ? C20A C19A C18A 108.9(6) . . ? C21A C20A C19A 112.2(6) . . ? O3A C21A C16A 107.3(5) . . ? O3A C21A C20A 112.5(5) . . ? C16A C21A C20A 112.2(6) . . ? C22 O3 C21 113.1(4) . . ? O3 C22 C23 107.9(4) . . ? C24 C23 C22 115.9(5) . . ? O4 C24 C23 110.5(4) . . ? C1 O4 C24 114.7(4) . . ? C22A O3A C21A 106.6(6) . . ? C23A C22A O3A 104.5(10) . . ? C22A C23A C24A 132.0(11) . . ? O4A C24A C23A 116.0(6) . . ? C1A O4A C24A 112.9(4) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.959 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.066 data_ama-173 _database_code_depnum_ccdc_archive 'CCDC 223730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N2 O5' _chemical_formula_weight 370.40 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 P212121 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 10.0266(3) _cell_length_b 11.8433(4) _cell_length_c 14.9627(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1776.79(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9427 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Crysta (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 7.35 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14029 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4047 _reflns_number_gt 3083 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997 COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. (1997)' _computing_publication_material 'WINGX(L.J. 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^)+(0.0500P)^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 SHELXL _refine_ls_extinction_coef 0.0169(16) _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 0.1(10) _refine_ls_number_reflns 4047 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 0.76593(17) 0.91589(15) 0.56811(11) 0.0192(4) Uani 1 1 d . . . C2 C 0.84095(18) 0.81280(15) 0.56422(11) 0.0216(4) Uani 1 1 d . . . C3 C 0.97633(18) 0.81477(17) 0.56631(12) 0.0253(4) Uani 1 1 d . . . H3 H 1.0252 0.7464 0.5608 0.030 Uiso 1 1 calc R . . C4 C 1.04496(18) 0.91852(17) 0.57666(12) 0.0272(4) Uani 1 1 d . . . H4 H 1.1397 0.9187 0.5776 0.033 Uiso 1 1 calc R . . C5 C 0.97808(17) 1.01800(17) 0.58523(13) 0.0251(4) Uani 1 1 d . . . H5 H 1.0259 1.0864 0.5939 0.030 Uiso 1 1 calc R . . C6 C 0.83713(17) 1.01910(15) 0.58119(11) 0.0194(4) Uani 1 1 d . . . C7 C 0.56901(18) 1.01329(15) 0.55999(11) 0.0205(4) Uani 1 1 d . . . C8 C 0.42985(18) 1.01576(16) 0.54158(11) 0.0230(4) Uani 1 1 d . . . H8 H 0.3832 0.9479 0.5286 0.028 Uiso 1 1 calc R . . C9 C 0.36463(18) 1.11589(16) 0.54276(12) 0.0259(4) Uani 1 1 d . . . H9 H 0.2724 1.1177 0.5283 0.031 Uiso 1 1 calc R . . C10 C 0.43043(18) 1.21802(16) 0.56506(12) 0.0247(4) Uani 1 1 d . . . H10 H 0.3814 1.2866 0.5667 0.030 Uiso 1 1 calc R . . C11 C 0.56321(18) 1.21886(15) 0.58417(11) 0.0222(4) Uani 1 1 d . . . C12 C 0.63899(17) 1.11625(15) 0.57868(11) 0.0198(4) Uani 1 1 d . . . C13 C 0.6987(2) 1.33468(16) 0.68170(13) 0.0308(5) Uani 1 1 d . . . H13A H 0.7319 1.4133 0.6853 0.037 Uiso 1 1 calc R . . H13B H 0.7772 1.2840 0.6796 0.037 Uiso 1 1 calc R . . C14 C 0.6195(2) 1.30899(17) 0.76396(13) 0.0363(5) Uani 1 1 d . . . H14A H 0.6652 1.3421 0.8164 0.044 Uiso 1 1 calc R . . H14B H 0.5308 1.3453 0.7589 0.044 Uiso 1 1 calc R . . C15 C 0.71288(19) 1.13865(17) 0.82057(13) 0.0289(4) Uani 1 1 d . . . H15A H 0.7295 1.1730 0.8798 0.035 Uiso 1 1 calc R . . H15B H 0.7939 1.1477 0.7835 0.035 Uiso 1 1 calc R . . C16 C 0.67816(19) 1.01502(16) 0.83051(13) 0.0283(4) Uani 1 1 d . . . H16A H 0.5914 1.0077 0.8616 0.034 Uiso 1 1 calc R . . H16B H 0.6693 0.9804 0.7706 0.034 Uiso 1 1 calc R . . C17 C 0.88826(19) 0.91713(17) 0.82795(12) 0.0290(4) Uani 1 1 d . . . H17A H 0.9720 0.9291 0.8617 0.035 Uiso 1 1 calc R . . H17B H 0.8940 0.9610 0.7718 0.035 Uiso 1 1 calc R . . C18 C 0.87352(19) 0.79382(17) 0.80626(12) 0.0295(5) Uani 1 1 d . . . H18A H 0.9575 0.7645 0.7803 0.035 Uiso 1 1 calc R . . H18B H 0.8539 0.7506 0.8614 0.035 Uiso 1 1 calc R . . C19 C 0.7518(2) 0.66876(16) 0.71163(12) 0.0315(5) Uani 1 1 d . . . H19A H 0.6959 0.6244 0.7534 0.038 Uiso 1 1 calc R . . H19B H 0.8398 0.6314 0.7066 0.038 Uiso 1 1 calc R . . C20 C 0.68633(18) 0.67474(16) 0.62187(12) 0.0263(4) Uani 1 1 d . . . H20A H 0.6501 0.5994 0.6065 0.032 Uiso 1 1 calc R . . H20B H 0.6106 0.7283 0.6248 0.032 Uiso 1 1 calc R . . N1 N 0.63327(14) 0.91333(13) 0.55688(9) 0.0203(3) Uani 1 1 d . . . N2 N 0.77200(14) 1.11841(12) 0.58893(9) 0.0207(3) Uani 1 1 d . . . O1 O 0.77712(12) 0.71050(10) 0.55212(8) 0.0250(3) Uani 1 1 d . . . O2 O 0.76767(12) 0.78097(10) 0.74417(8) 0.0268(3) Uani 1 1 d . . . O3 O 0.77798(13) 0.95698(11) 0.87982(8) 0.0297(3) Uani 1 1 d . . . O4 O 0.60170(13) 1.19095(11) 0.77860(8) 0.0312(3) Uani 1 1 d . . . O5 O 0.62290(12) 1.32131(10) 0.60027(8) 0.0265(3) 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 0.0219(9) 0.0200(9) 0.0158(8) -0.0022(7) 0.0016(7) -0.0016(8) C2 0.0234(9) 0.0201(9) 0.0212(9) -0.0049(8) 0.0026(8) -0.0005(8) C3 0.0258(10) 0.0232(10) 0.0268(10) -0.0016(8) 0.0029(8) 0.0033(8) C4 0.0184(9) 0.0337(11) 0.0296(10) -0.0032(9) 0.0030(8) 0.0011(9) C5 0.0229(9) 0.0252(11) 0.0273(10) -0.0032(8) 0.0016(8) -0.0051(8) C6 0.0201(8) 0.0212(10) 0.0168(8) -0.0021(7) 0.0017(8) -0.0015(8) C7 0.0228(9) 0.0215(10) 0.0170(8) 0.0024(7) 0.0020(7) -0.0016(8) C8 0.0218(9) 0.0256(10) 0.0214(9) -0.0019(8) 0.0011(8) -0.0019(8) C9 0.0204(9) 0.0331(11) 0.0242(9) 0.0008(8) -0.0027(8) 0.0048(9) C10 0.0263(10) 0.0232(10) 0.0246(9) 0.0035(8) -0.0001(8) 0.0061(8) C11 0.0274(9) 0.0200(9) 0.0191(8) 0.0033(7) 0.0028(8) -0.0002(8) C12 0.0222(9) 0.0204(9) 0.0166(8) 0.0006(7) 0.0019(8) 0.0004(8) C13 0.0351(11) 0.0203(10) 0.0371(11) -0.0036(9) -0.0044(9) -0.0033(9) C14 0.0501(12) 0.0276(11) 0.0312(10) -0.0033(9) 0.0019(10) 0.0092(10) C15 0.0331(10) 0.0306(11) 0.0230(9) 0.0001(8) -0.0049(9) 0.0011(9) C16 0.0278(10) 0.0315(11) 0.0256(9) 0.0019(9) -0.0014(8) -0.0003(9) C17 0.0270(10) 0.0371(12) 0.0229(9) -0.0025(9) -0.0025(8) -0.0016(10) C18 0.0288(10) 0.0349(12) 0.0247(10) -0.0002(8) -0.0022(8) 0.0081(10) C19 0.0428(12) 0.0197(10) 0.0321(10) -0.0010(8) -0.0001(10) 0.0003(9) C20 0.0292(10) 0.0188(10) 0.0308(10) 0.0004(8) 0.0029(9) -0.0033(8) N1 0.0206(8) 0.0204(8) 0.0198(7) -0.0012(6) 0.0015(6) -0.0016(7) N2 0.0223(7) 0.0205(8) 0.0192(7) 0.0001(6) 0.0017(7) -0.0020(7) O1 0.0270(7) 0.0194(6) 0.0286(7) -0.0048(6) 0.0046(6) -0.0014(6) O2 0.0327(7) 0.0225(7) 0.0251(7) -0.0013(6) -0.0040(6) 0.0016(6) O3 0.0361(7) 0.0314(8) 0.0216(6) 0.0001(6) -0.0016(6) 0.0058(6) O4 0.0334(7) 0.0317(8) 0.0284(7) 0.0034(6) 0.0009(6) 0.0052(6) O5 0.0328(7) 0.0172(7) 0.0295(7) 0.0022(5) 0.0003(6) -0.0016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.341(2) . ? C1 C6 1.429(2) . ? C1 C2 1.435(2) . ? C2 C3 1.358(3) . ? C2 O1 1.382(2) . ? C3 C4 1.417(3) . ? C3 H3 0.9500 . ? C4 C5 1.362(3) . ? C4 H4 0.9500 . ? C5 C6 1.415(2) . ? C5 H5 0.9500 . ? C6 N2 1.350(2) . ? C7 N1 1.349(2) . ? C7 C8 1.423(3) . ? C7 C12 1.434(2) . ? C8 C9 1.354(3) . ? C8 H8 0.9500 . ? C9 C10 1.418(3) . ? C9 H9 0.9500 . ? C10 C11 1.362(3) . ? C10 H10 0.9500 . ? C11 O5 1.374(2) . ? C11 C12 1.436(2) . ? C12 N2 1.343(2) . ? C13 O5 1.445(2) . ? C13 C14 1.496(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O4 1.426(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O4 1.422(2) . ? C15 C16 1.512(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O3 1.421(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O3 1.431(2) . ? C17 C18 1.503(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O2 1.419(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O2 1.424(2) . ? C19 C20 1.496(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O1 1.448(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? 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 N1 C1 C6 122.15(16) . . ? N1 C1 C2 119.70(16) . . ? C6 C1 C2 118.12(15) . . ? C3 C2 O1 118.75(16) . . ? C3 C2 C1 120.55(17) . . ? O1 C2 C1 120.55(15) . . ? C2 C3 C4 120.19(18) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 121.43(17) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.73(18) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? N2 C6 C5 119.18(16) . . ? N2 C6 C1 121.01(15) . . ? C5 C6 C1 119.81(16) . . ? N1 C7 C8 118.68(16) . . ? N1 C7 C12 121.28(15) . . ? C8 C7 C12 120.01(16) . . ? C9 C8 C7 119.28(17) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 121.70(16) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 120.71(17) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 O5 117.97(16) . . ? C10 C11 C12 119.95(17) . . ? O5 C11 C12 121.80(15) . . ? N2 C12 C7 121.63(16) . . ? N2 C12 C11 120.20(16) . . ? C7 C12 C11 118.15(15) . . ? O5 C13 C14 113.07(15) . . ? O5 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? O5 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O4 C14 C13 113.08(16) . . ? O4 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? O4 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? O4 C15 C16 106.54(15) . . ? O4 C15 H15A 110.4 . . ? C16 C15 H15A 110.4 . . ? O4 C15 H15B 110.4 . . ? C16 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? O3 C16 C15 110.93(15) . . ? O3 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? O3 C17 C18 111.19(16) . . ? O3 C17 H17A 109.4 . . ? C18 C17 H17A 109.4 . . ? O3 C17 H17B 109.4 . . ? C18 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O2 C18 C17 108.62(15) . . ? O2 C18 H18A 110.0 . . ? C17 C18 H18A 110.0 . . ? O2 C18 H18B 110.0 . . ? C17 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? O2 C19 C20 108.16(15) . . ? O2 C19 H19A 110.1 . . ? C20 C19 H19A 110.1 . . ? O2 C19 H19B 110.1 . . ? C20 C19 H19B 110.1 . . ? H19A C19 H19B 108.4 . . ? O1 C20 C19 112.65(15) . . ? O1 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? O1 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C1 N1 C7 116.72(15) . . ? C12 N2 C6 117.00(15) . . ? C2 O1 C20 116.93(13) . . ? C18 O2 C19 114.07(14) . . ? C16 O3 C17 114.98(14) . . ? C15 O4 C14 113.39(15) . . ? C11 O5 C13 118.28(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.341 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.049