# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Li, Chaozhong' 'Chen, Pinhong' 'Cao, Lidong' 'Tian, Wenhai' 'Wang, Xinfeng' _publ_contact_author_name 'Li, Chaozhong' _publ_contact_author_email clig@mail.sioc.ac.cn _publ_section_title ; Total synthesis and absolute configuration determination of (+)-subincanadine F ; # Attachment '- Compd 6.cif' data_cd2822 _database_code_depnum_ccdc_archive 'CCDC 790864' #TrackingRef '- Compd 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N2 O4' _chemical_formula_weight 326.34 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4790(16) _cell_length_b 10.0749(17) _cell_length_c 18.579(3) _cell_angle_alpha 95.772(3) _cell_angle_beta 97.284(4) _cell_angle_gamma 114.575(3) _cell_volume 1577.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1978 _cell_measurement_theta_min 4.468 _cell_measurement_theta_max 44.525 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.227 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.78473 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9381 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6705 _reflns_number_gt 3682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6705 _refine_ls_number_parameters 436 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_restrained_S_all 0.884 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2570(3) 0.3712(2) 0.09299(13) 0.0916(7) Uani 1 1 d . . . O2 O 0.4402(2) 0.0794(2) 0.28354(10) 0.0800(6) Uani 1 1 d . . . O3 O 0.7923(3) 0.0862(3) 0.19861(15) 0.1099(10) Uani 1 1 d . . . O4 O 0.54984(19) -0.09363(17) 0.18535(8) 0.0548(4) Uani 1 1 d . . . O5 O 0.2724(2) 1.10211(18) 0.58252(9) 0.0695(5) Uani 1 1 d . . . O6 O 0.0465(3) 0.88144(19) 0.28260(11) 0.0864(7) Uani 1 1 d . . . O7 O -0.3385(3) 0.4716(3) 0.33963(12) 0.1068(10) Uani 1 1 d . . . O8 O -0.1149(2) 0.57060(19) 0.29907(10) 0.0777(6) Uani 1 1 d . . . N1 N 0.1551(2) 0.1460(2) 0.12646(12) 0.0577(6) Uani 1 1 d . . . N2 N 0.5901(2) 0.09506(19) 0.12350(10) 0.0466(5) Uani 1 1 d . . . N3 N 0.3236(2) 1.02215(18) 0.47536(11) 0.0481(5) Uani 1 1 d . . . N4 N -0.1121(2) 0.61672(18) 0.41957(10) 0.0451(5) Uani 1 1 d . . . C1 C 0.2286(3) 0.2401(3) 0.08144(16) 0.0641(7) Uani 1 1 d . . . C2 C 0.2823(3) 0.1775(3) 0.02010(15) 0.0665(8) Uani 1 1 d . . . H2A H 0.3119 0.2456 -0.0146 0.080 Uiso 1 1 calc R . . H2B H 0.1973 0.0845 -0.0058 0.080 Uiso 1 1 calc R . . C3 C 0.4220(3) 0.1526(2) 0.05167(13) 0.0509(6) Uani 1 1 d . . . C4 C 0.4345(3) 0.0812(2) 0.10853(13) 0.0467(6) Uani 1 1 d . . . C5 C 0.3162(3) 0.0136(2) 0.15679(12) 0.0478(6) Uani 1 1 d . . . H5 H 0.3072 -0.0856 0.1612 0.057 Uiso 1 1 calc R . . C6 C 0.1555(3) 0.0005(3) 0.12212(14) 0.0562(6) Uani 1 1 d . . . H6A H 0.1295 -0.0463 0.0709 0.067 Uiso 1 1 calc R . . H6B H 0.0756 -0.0616 0.1474 0.067 Uiso 1 1 calc R . . C7 C 0.1718(3) 0.2112(3) 0.20258(15) 0.0643(7) Uani 1 1 d . . . H7A H 0.0898 0.1441 0.2252 0.077 Uiso 1 1 calc R . . H7B H 0.1614 0.3032 0.2041 0.077 Uiso 1 1 calc R . . C8 C 0.3336(3) 0.2404(3) 0.24413(14) 0.0624(7) Uani 1 1 d . . . H8A H 0.4136 0.3222 0.2275 0.075 Uiso 1 1 calc R . . H8B H 0.3396 0.2698 0.2962 0.075 Uiso 1 1 calc R . . C9 C 0.3690(3) 0.1079(3) 0.23387(14) 0.0545(6) Uani 1 1 d . . . C10 C 0.5707(3) 0.2137(2) 0.02897(12) 0.0492(6) Uani 1 1 d . . . C11 C 0.6755(3) 0.1779(2) 0.07392(12) 0.0466(6) Uani 1 1 d . . . C12 C 0.8291(3) 0.2200(3) 0.06543(14) 0.0569(7) Uani 1 1 d . . . H12 H 0.8972 0.1952 0.0957 0.068 Uiso 1 1 calc R . . C13 C 0.8785(3) 0.3007(3) 0.01010(15) 0.0621(7) Uani 1 1 d . . . H13 H 0.9813 0.3289 0.0024 0.074 Uiso 1 1 calc R . . C14 C 0.7790(3) 0.3404(3) -0.03391(14) 0.0633(7) Uani 1 1 d . . . H14 H 0.8165 0.3967 -0.0699 0.076 Uiso 1 1 calc R . . C15 C 0.6262(3) 0.2983(3) -0.02537(13) 0.0587(7) Uani 1 1 d . . . H15 H 0.5598 0.3254 -0.0553 0.070 Uiso 1 1 calc R . . C16 C 0.6543(3) 0.0304(3) 0.17242(15) 0.0602(7) Uani 1 1 d . . . C17 C 0.6048(4) -0.1637(3) 0.24010(16) 0.0792(9) Uani 1 1 d . . . H17A H 0.6515 -0.0959 0.2866 0.095 Uiso 1 1 calc R . . H17B H 0.6841 -0.1907 0.2239 0.095 Uiso 1 1 calc R . . C18 C 0.4680(4) -0.2965(3) 0.24912(19) 0.0989(11) Uani 1 1 d . . . H18A H 0.3885 -0.2690 0.2632 0.128 Uiso 1 1 calc R . . H18B H 0.5002 -0.3424 0.2866 0.128 Uiso 1 1 calc R . . H18C H 0.4258 -0.3649 0.2034 0.128 Uiso 1 1 calc R . . C19 C 0.2841(3) 1.0046(3) 0.54239(14) 0.0519(6) Uani 1 1 d . . . C20 C 0.2431(3) 0.8526(2) 0.56320(13) 0.0558(7) Uani 1 1 d . . . H20A H 0.3264 0.8230 0.5566 0.067 Uiso 1 1 calc R . . H20B H 0.2320 0.8551 0.6144 0.067 Uiso 1 1 calc R . . C21 C 0.0895(3) 0.7436(2) 0.51423(13) 0.0444(6) Uani 1 1 d . . . C22 C 0.0478(3) 0.7237(2) 0.43995(13) 0.0426(5) Uani 1 1 d . . . C23 C 0.1436(3) 0.7999(2) 0.38555(12) 0.0438(5) Uani 1 1 d . . . H23 H 0.1431 0.7245 0.3477 0.053 Uiso 1 1 calc R . . C24 C 0.3147(3) 0.8976(2) 0.42483(13) 0.0482(6) Uani 1 1 d . . . H24A H 0.3546 0.8391 0.4519 0.058 Uiso 1 1 calc R . . H24B H 0.3803 0.9342 0.3886 0.058 Uiso 1 1 calc R . . C25 C 0.2830(3) 1.1244(2) 0.43725(14) 0.0559(7) Uani 1 1 d . . . H25A H 0.3533 1.1621 0.4029 0.067 Uiso 1 1 calc R . . H25B H 0.2939 1.2076 0.4724 0.067 Uiso 1 1 calc R . . C26 C 0.1123(3) 1.0411(2) 0.39584(14) 0.0557(7) Uani 1 1 d . . . H26A H 0.0415 1.0160 0.4309 0.067 Uiso 1 1 calc R . . H26B H 0.0866 1.1040 0.3657 0.067 Uiso 1 1 calc R . . C27 C 0.0901(3) 0.9027(2) 0.34806(14) 0.0493(6) Uani 1 1 d . . . C28 C -0.0431(3) 0.6495(2) 0.54267(13) 0.0466(6) Uani 1 1 d . . . C29 C -0.1688(3) 0.5735(2) 0.48357(13) 0.0463(6) Uani 1 1 d . . . C30 C -0.3165(3) 0.4756(2) 0.49364(16) 0.0585(7) Uani 1 1 d . . . H30 H -0.3995 0.4254 0.4540 0.070 Uiso 1 1 calc R . . C31 C -0.3355(3) 0.4558(3) 0.56486(18) 0.0670(8) Uani 1 1 d . . . H31 H -0.4336 0.3916 0.5733 0.080 Uiso 1 1 calc R . . C32 C -0.2122(4) 0.5291(3) 0.62379(17) 0.0649(7) Uani 1 1 d . . . H32 H -0.2284 0.5121 0.6710 0.078 Uiso 1 1 calc R . . C33 C -0.0667(3) 0.6260(2) 0.61417(14) 0.0567(7) Uani 1 1 d . . . H33 H 0.0152 0.6756 0.6543 0.068 Uiso 1 1 calc R . . C34 C -0.2014(3) 0.5462(3) 0.35034(16) 0.0641(7) Uani 1 1 d . . . C35 C -0.1949(5) 0.5048(4) 0.22335(17) 0.1147(14) Uani 1 1 d . . . H35A H -0.2327 0.3982 0.2172 0.128 Uiso 1 1 calc R . . H35B H -0.2854 0.5261 0.2123 0.128 Uiso 1 1 calc R . . C36 C -0.0930(7) 0.5607(5) 0.1753(2) 0.113(3) Uani 1 1 d . . . H36A H -0.0334 0.6658 0.1904 0.135 Uiso 1 1 calc R . . H36B H -0.1528 0.5403 0.1264 0.135 Uiso 1 1 calc R . . H36C H -0.0222 0.5148 0.1756 0.135 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 0.0959(16) 0.0719(13) 0.1256(18) 0.0370(13) 0.0198(14) 0.0500(13) O2 0.0951(16) 0.1075(16) 0.0575(12) 0.0140(11) 0.0054(11) 0.0658(13) O3 0.0558(14) 0.124(2) 0.138(2) 0.0969(18) 0.0034(14) 0.0297(14) O4 0.0614(11) 0.0486(9) 0.0548(10) 0.0172(8) 0.0046(8) 0.0240(9) O5 0.0851(14) 0.0475(10) 0.0610(11) -0.0065(9) 0.0089(10) 0.0193(10) O6 0.1189(18) 0.0544(11) 0.0659(13) 0.0047(9) -0.0183(12) 0.0297(11) O7 0.0553(14) 0.131(2) 0.0874(16) -0.0065(15) -0.0087(12) -0.0267(15) O8 0.0727(13) 0.0649(12) 0.0556(12) -0.0088(9) -0.0006(10) -0.0007(10) N1 0.0473(13) 0.0579(13) 0.0696(14) 0.0137(11) 0.0056(11) 0.0255(11) N2 0.0441(12) 0.0439(10) 0.0501(11) 0.0122(9) 0.0023(9) 0.0184(9) N3 0.0442(12) 0.0337(10) 0.0566(12) -0.0005(9) 0.0053(10) 0.0103(9) N4 0.0392(11) 0.0315(9) 0.0574(12) 0.0024(9) 0.0008(10) 0.0117(8) C1 0.0493(16) 0.0673(18) 0.083(2) 0.0218(16) 0.0011(15) 0.0331(15) C2 0.0559(17) 0.0817(19) 0.0670(18) 0.0275(15) 0.0043(14) 0.0337(15) C3 0.0508(15) 0.0524(14) 0.0500(14) 0.0139(11) 0.0038(12) 0.0235(12) C4 0.0428(14) 0.0439(12) 0.0507(14) 0.0078(11) 0.0023(11) 0.0181(11) C5 0.0428(14) 0.0425(12) 0.0561(15) 0.0134(11) 0.0068(12) 0.0160(11) C6 0.0442(15) 0.0527(14) 0.0638(16) 0.0083(12) 0.0025(12) 0.0160(12) C7 0.0545(17) 0.0639(16) 0.0756(19) 0.0039(14) 0.0095(14) 0.0292(14) C8 0.0579(17) 0.0571(15) 0.0649(17) 0.0027(13) 0.0034(14) 0.0219(14) C9 0.0415(14) 0.0612(15) 0.0563(16) 0.0151(13) 0.0069(12) 0.0176(12) C10 0.0493(15) 0.0446(13) 0.0478(14) 0.0074(11) 0.0033(12) 0.0165(12) C11 0.0457(14) 0.0401(12) 0.0483(14) 0.0062(10) 0.0037(11) 0.0147(11) C12 0.0496(16) 0.0516(14) 0.0653(17) 0.0090(13) 0.0056(13) 0.0197(13) C13 0.0543(17) 0.0538(15) 0.0686(18) 0.0058(13) 0.0180(14) 0.0135(13) C14 0.0680(19) 0.0549(15) 0.0569(16) 0.0138(13) 0.0151(14) 0.0152(14) C15 0.0664(19) 0.0558(15) 0.0505(15) 0.0132(12) 0.0042(13) 0.0243(14) C16 0.0474(16) 0.0682(17) 0.0668(17) 0.0250(14) 0.0053(14) 0.0253(15) C17 0.094(2) 0.082(2) 0.0720(19) 0.0381(16) 0.0090(17) 0.0444(19) C18 0.113(3) 0.081(2) 0.098(2) 0.0489(19) 0.014(2) 0.031(2) C19 0.0407(14) 0.0420(13) 0.0553(16) 0.0009(12) -0.0054(12) 0.0065(11) C20 0.0528(15) 0.0471(13) 0.0543(15) 0.0090(11) -0.0010(12) 0.0121(12) C21 0.0440(14) 0.0298(11) 0.0546(15) 0.0054(10) 0.0022(11) 0.0138(10) C22 0.0380(13) 0.0277(10) 0.0583(15) 0.0046(10) 0.0033(11) 0.0127(10) C23 0.0424(13) 0.0311(11) 0.0527(13) -0.0001(10) 0.0039(11) 0.0139(10) C24 0.0418(14) 0.0396(12) 0.0603(15) 0.0050(11) 0.0078(11) 0.0163(11) C25 0.0659(17) 0.0319(11) 0.0631(16) 0.0042(11) 0.0112(13) 0.0156(12) C26 0.0616(17) 0.0457(13) 0.0651(16) 0.0118(12) 0.0106(13) 0.0283(13) C27 0.0419(14) 0.0404(13) 0.0548(16) 0.0071(11) 0.0010(12) 0.0099(11) C28 0.0531(15) 0.0310(11) 0.0597(15) 0.0098(11) 0.0113(13) 0.0213(11) C29 0.0430(14) 0.0282(11) 0.0680(16) 0.0091(11) 0.0088(12) 0.0160(10) C30 0.0505(16) 0.0375(13) 0.088(2) 0.0126(13) 0.0160(14) 0.0185(12) C31 0.0642(19) 0.0433(14) 0.102(2) 0.0210(15) 0.0336(18) 0.0241(14) C32 0.081(2) 0.0471(15) 0.080(2) 0.0240(14) 0.0358(17) 0.0318(15) C33 0.0692(18) 0.0371(12) 0.0670(17) 0.0096(12) 0.0137(14) 0.0256(13) C34 0.0549(18) 0.0460(14) 0.0667(18) 0.0039(13) -0.0054(16) 0.0041(14) C35 0.117(3) 0.098(3) 0.063(2) -0.0113(19) 0.005(2) -0.008(2) C36 0.156(8) 0.088(3) 0.060(3) -0.033(3) 0.046(4) -0.022(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.222(3) . ? O2 C9 1.202(3) . ? O3 C16 1.198(3) . ? O4 C16 1.301(3) . ? O4 C17 1.456(3) . ? O5 C19 1.224(3) . ? O6 C27 1.201(3) . ? O7 C34 1.178(3) . ? O8 C34 1.310(3) . ? O8 C35 1.455(3) . ? N1 C1 1.358(3) . ? N1 C7 1.458(3) . ? N1 C6 1.461(3) . ? N2 C16 1.389(3) . ? N2 C11 1.408(3) . ? N2 C4 1.410(3) . ? N3 C19 1.352(3) . ? N3 C24 1.455(3) . ? N3 C25 1.455(3) . ? N4 C34 1.384(3) . ? N4 C29 1.401(3) . ? N4 C22 1.420(3) . ? C1 C2 1.492(4) . ? C2 C3 1.506(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.356(3) . ? C3 C10 1.423(3) . ? C4 C5 1.506(3) . ? C5 C6 1.523(3) . ? C5 C9 1.534(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.521(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.507(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C15 1.399(3) . ? C10 C11 1.401(3) . ? C11 C12 1.372(3) . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 C15 1.365(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.469(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.519(3) . ? C20 C21 1.512(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.357(3) . ? C21 C28 1.427(3) . ? C22 C23 1.498(3) . ? C23 C27 1.519(3) . ? C23 C24 1.537(3) . ? C23 H23 0.9800 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.530(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.495(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C28 C29 1.397(3) . ? C28 C33 1.402(3) . ? C29 C30 1.386(3) . ? C30 C31 1.381(4) . ? C30 H30 0.9300 . ? C31 C32 1.381(4) . ? C31 H31 0.9300 . ? C32 C33 1.365(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C35 C36 1.384(5) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? 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 C16 O4 C17 116.6(2) . . ? C34 O8 C35 117.6(2) . . ? C1 N1 C7 116.7(2) . . ? C1 N1 C6 120.4(2) . . ? C7 N1 C6 111.1(2) . . ? C16 N2 C11 122.1(2) . . ? C16 N2 C4 129.2(2) . . ? C11 N2 C4 108.45(18) . . ? C19 N3 C24 120.81(19) . . ? C19 N3 C25 117.3(2) . . ? C24 N3 C25 112.35(18) . . ? C34 N4 C29 121.3(2) . . ? C34 N4 C22 129.6(2) . . ? C29 N4 C22 108.57(18) . . ? O1 C1 N1 121.7(3) . . ? O1 C1 C2 121.7(3) . . ? N1 C1 C2 116.5(2) . . ? C1 C2 C3 108.8(2) . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C10 108.4(2) . . ? C4 C3 C2 127.7(2) . . ? C10 C3 C2 123.8(2) . . ? C3 C4 N2 108.5(2) . . ? C3 C4 C5 128.7(2) . . ? N2 C4 C5 122.42(19) . . ? C4 C5 C6 109.80(18) . . ? C4 C5 C9 110.80(18) . . ? C6 C5 C9 109.6(2) . . ? C4 C5 H5 108.9 . . ? C6 C5 H5 108.9 . . ? C9 C5 H5 108.9 . . ? N1 C6 C5 111.09(19) . . ? N1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N1 C7 C8 108.5(2) . . ? N1 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? N1 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C9 C8 C7 113.1(2) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O2 C9 C8 121.4(2) . . ? O2 C9 C5 121.1(2) . . ? C8 C9 C5 117.5(2) . . ? C15 C10 C11 118.6(2) . . ? C15 C10 C3 133.3(2) . . ? C11 C10 C3 108.1(2) . . ? C12 C11 C10 122.4(2) . . ? C12 C11 N2 131.0(2) . . ? C10 C11 N2 106.6(2) . . ? C11 C12 C13 117.3(2) . . ? C11 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 119.2(2) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? O3 C16 O4 125.3(2) . . ? O3 C16 N2 121.8(2) . . ? O4 C16 N2 112.9(2) . . ? O4 C17 C18 107.8(2) . . ? O4 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? O4 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 N3 122.3(2) . . ? O5 C19 C20 121.3(2) . . ? N3 C19 C20 116.3(2) . . ? C21 C20 C19 108.28(18) . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C22 C21 C28 108.58(19) . . ? C22 C21 C20 128.5(2) . . ? C28 C21 C20 122.7(2) . . ? C21 C22 N4 107.92(19) . . ? C21 C22 C23 128.98(19) . . ? N4 C22 C23 123.07(19) . . ? C22 C23 C27 115.61(19) . . ? C22 C23 C24 109.51(18) . . ? C27 C23 C24 105.35(17) . . ? C22 C23 H23 108.7 . . ? C27 C23 H23 108.7 . . ? C24 C23 H23 108.7 . . ? N3 C24 C23 110.69(18) . . ? N3 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? N3 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? N3 C25 C26 108.27(17) . . ? N3 C25 H25A 110.0 . . ? C26 C25 H25A 110.0 . . ? N3 C25 H25B 110.0 . . ? C26 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C27 C26 C25 110.4(2) . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? O6 C27 C26 121.5(2) . . ? O6 C27 C23 121.9(2) . . ? C26 C27 C23 116.2(2) . . ? C29 C28 C33 119.1(2) . . ? C29 C28 C21 108.0(2) . . ? C33 C28 C21 132.9(2) . . ? C30 C29 C28 121.8(2) . . ? C30 C29 N4 131.2(2) . . ? C28 C29 N4 106.9(2) . . ? C31 C30 C29 117.4(3) . . ? C31 C30 H30 121.3 . . ? C29 C30 H30 121.3 . . ? C32 C31 C30 121.5(3) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? C33 C32 C31 121.3(3) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C28 118.8(2) . . ? C32 C33 H33 120.6 . . ? C28 C33 H33 120.6 . . ? O7 C34 O8 124.6(3) . . ? O7 C34 N4 123.4(3) . . ? O8 C34 N4 112.1(2) . . ? C36 C35 O8 110.4(3) . . ? C36 C35 H35A 109.6 . . ? O8 C35 H35A 109.6 . . ? C36 C35 H35B 109.6 . . ? O8 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 O1 -25.8(4) . . . . ? C6 N1 C1 O1 -165.5(2) . . . . ? C7 N1 C1 C2 150.3(2) . . . . ? C6 N1 C1 C2 10.6(3) . . . . ? O1 C1 C2 C3 104.2(3) . . . . ? N1 C1 C2 C3 -71.9(3) . . . . ? C1 C2 C3 C4 50.1(3) . . . . ? C1 C2 C3 C10 -124.4(3) . . . . ? C10 C3 C4 N2 0.1(3) . . . . ? C2 C3 C4 N2 -175.0(2) . . . . ? C10 C3 C4 C5 172.5(2) . . . . ? C2 C3 C4 C5 -2.7(4) . . . . ? C16 N2 C4 C3 -174.1(2) . . . . ? C11 N2 C4 C3 0.0(2) . . . . ? C16 N2 C4 C5 12.9(4) . . . . ? C11 N2 C4 C5 -172.99(19) . . . . ? C3 C4 C5 C6 14.2(3) . . . . ? N2 C4 C5 C6 -174.4(2) . . . . ? C3 C4 C5 C9 -107.0(3) . . . . ? N2 C4 C5 C9 64.4(3) . . . . ? C1 N1 C6 C5 74.7(3) . . . . ? C7 N1 C6 C5 -67.1(3) . . . . ? C4 C5 C6 N1 -71.2(3) . . . . ? C9 C5 C6 N1 50.7(3) . . . . ? C1 N1 C7 C8 -78.4(3) . . . . ? C6 N1 C7 C8 64.9(3) . . . . ? N1 C7 C8 C9 -50.2(3) . . . . ? C7 C8 C9 O2 -142.5(3) . . . . ? C7 C8 C9 C5 39.7(3) . . . . ? C4 C5 C9 O2 -95.3(3) . . . . ? C6 C5 C9 O2 143.4(2) . . . . ? C4 C5 C9 C8 82.4(3) . . . . ? C6 C5 C9 C8 -38.9(3) . . . . ? C4 C3 C10 C15 -179.1(2) . . . . ? C2 C3 C10 C15 -3.7(4) . . . . ? C4 C3 C10 C11 -0.2(3) . . . . ? C2 C3 C10 C11 175.2(2) . . . . ? C15 C10 C11 C12 -1.5(3) . . . . ? C3 C10 C11 C12 179.4(2) . . . . ? C15 C10 C11 N2 179.3(2) . . . . ? C3 C10 C11 N2 0.2(2) . . . . ? C16 N2 C11 C12 -4.6(4) . . . . ? C4 N2 C11 C12 -179.2(2) . . . . ? C16 N2 C11 C10 174.5(2) . . . . ? C4 N2 C11 C10 -0.1(2) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? N2 C11 C12 C13 179.1(2) . . . . ? C11 C12 C13 C14 1.4(4) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C11 C10 C15 C14 1.4(3) . . . . ? C3 C10 C15 C14 -179.8(2) . . . . ? C17 O4 C16 O3 4.6(4) . . . . ? C17 O4 C16 N2 -175.7(2) . . . . ? C11 N2 C16 O3 32.7(4) . . . . ? C4 N2 C16 O3 -154.0(3) . . . . ? C11 N2 C16 O4 -147.0(2) . . . . ? C4 N2 C16 O4 26.3(4) . . . . ? C16 O4 C17 C18 177.0(3) . . . . ? C24 N3 C19 O5 -171.2(2) . . . . ? C25 N3 C19 O5 -27.5(3) . . . . ? C24 N3 C19 C20 4.4(3) . . . . ? C25 N3 C19 C20 148.2(2) . . . . ? O5 C19 C20 C21 107.5(3) . . . . ? N3 C19 C20 C21 -68.1(3) . . . . ? C19 C20 C21 C22 48.5(3) . . . . ? C19 C20 C21 C28 -126.5(2) . . . . ? C28 C21 C22 N4 0.0(2) . . . . ? C20 C21 C22 N4 -175.6(2) . . . . ? C28 C21 C22 C23 178.0(2) . . . . ? C20 C21 C22 C23 2.4(4) . . . . ? C34 N4 C22 C21 -171.0(2) . . . . ? C29 N4 C22 C21 1.2(2) . . . . ? C34 N4 C22 C23 10.8(3) . . . . ? C29 N4 C22 C23 -176.92(19) . . . . ? C21 C22 C23 C27 -111.4(3) . . . . ? N4 C22 C23 C27 66.3(3) . . . . ? C21 C22 C23 C24 7.4(3) . . . . ? N4 C22 C23 C24 -174.92(18) . . . . ? C19 N3 C24 C23 79.4(3) . . . . ? C25 N3 C24 C23 -66.0(2) . . . . ? C22 C23 C24 N3 -68.3(2) . . . . ? C27 C23 C24 N3 56.6(2) . . . . ? C19 N3 C25 C26 -84.9(2) . . . . ? C24 N3 C25 C26 61.7(2) . . . . ? N3 C25 C26 C27 -53.0(3) . . . . ? C25 C26 C27 O6 -120.8(3) . . . . ? C25 C26 C27 C23 52.4(3) . . . . ? C22 C23 C27 O6 -118.2(3) . . . . ? C24 C23 C27 O6 120.8(3) . . . . ? C22 C23 C27 C26 68.6(3) . . . . ? C24 C23 C27 C26 -52.4(3) . . . . ? C22 C21 C28 C29 -1.3(2) . . . . ? C20 C21 C28 C29 174.6(2) . . . . ? C22 C21 C28 C33 -179.4(2) . . . . ? C20 C21 C28 C33 -3.5(4) . . . . ? C33 C28 C29 C30 0.1(3) . . . . ? C21 C28 C29 C30 -178.3(2) . . . . ? C33 C28 C29 N4 -179.54(19) . . . . ? C21 C28 C29 N4 2.0(2) . . . . ? C34 N4 C29 C30 -8.6(4) . . . . ? C22 N4 C29 C30 178.4(2) . . . . ? C34 N4 C29 C28 171.0(2) . . . . ? C22 N4 C29 C28 -2.0(2) . . . . ? C28 C29 C30 C31 0.1(3) . . . . ? N4 C29 C30 C31 179.7(2) . . . . ? C29 C30 C31 C32 -0.7(4) . . . . ? C30 C31 C32 C33 1.0(4) . . . . ? C31 C32 C33 C28 -0.7(4) . . . . ? C29 C28 C33 C32 0.2(3) . . . . ? C21 C28 C33 C32 178.1(2) . . . . ? C35 O8 C34 O7 2.1(5) . . . . ? C35 O8 C34 N4 -178.9(2) . . . . ? C29 N4 C34 O7 17.6(4) . . . . ? C22 N4 C34 O7 -171.0(3) . . . . ? C29 N4 C34 O8 -161.4(2) . . . . ? C22 N4 C34 O8 10.0(3) . . . . ? C34 O8 C35 C36 169.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.439 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.046 # Attachment '- Compd 7.cif' data_cd2811 _database_code_depnum_ccdc_archive 'CCDC 790865' #TrackingRef '- Compd 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N2 O5' _chemical_formula_weight 342.34 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 11.549(2) _cell_length_b 14.458(3) _cell_length_c 9.7091(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.904(3) _cell_angle_gamma 90.00 _cell_volume 1591.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1046 _cell_measurement_theta_min 4.565 _cell_measurement_theta_max 40.910 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.252 _exptl_crystal_size_mid 0.159 _exptl_crystal_size_min 0.046 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75258 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8206 _diffrn_reflns_av_R_equivalents 0.1086 _diffrn_reflns_av_sigmaI/netI 0.1041 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2955 _reflns_number_gt 1677 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2955 _refine_ls_number_parameters 239 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1423 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.2148 _refine_ls_wR_factor_gt 0.1856 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1010(3) 0.0699(2) 0.4574(4) 0.0514(10) Uani 1 1 d . . . N2 N 0.3538(2) 0.2811(2) 0.6319(3) 0.0466(9) Uani 1 1 d . . . O1 O 0.0214(2) 0.1437(2) 0.2572(3) 0.0601(9) Uani 1 1 d . . . O2 O -0.0357(2) 0.2194(2) 0.5659(3) 0.0619(9) Uani 1 1 d . . . H2 H -0.0190 0.2565 0.6305 0.093 Uiso 1 1 calc R . . O3 O 0.4689(3) 0.2016(3) 0.8102(5) 0.1123(17) Uani 1 1 d . . . O4 O 0.5441(2) 0.3150(2) 0.6993(3) 0.0696(10) Uani 1 1 d . . . O5 O 0.4329(7) 0.0332(9) 0.6306(8) 0.109(6) Uani 0.485(14) 1 d PD A 1 O5' O 0.4389(7) 0.1055(6) 0.5102(18) 0.126(9) Uani 0.515(14) 1 d PD A 2 C1 C 0.0511(3) 0.1442(3) 0.3861(5) 0.0459(10) Uani 1 1 d . . . C2 C 0.0401(3) 0.2329(3) 0.4689(5) 0.0473(11) Uani 1 1 d . . . H2A H 0.0029 0.2794 0.4013 0.057 Uiso 1 1 calc R . . C3 C 0.1626(3) 0.2686(3) 0.5317(4) 0.0424(10) Uani 1 1 d . . . C4 C 0.2570(3) 0.2210(3) 0.6023(4) 0.0480(11) Uani 1 1 d . . . C5 C 0.2683(4) 0.1195(3) 0.6372(5) 0.0627(14) Uani 1 1 d . A . H5 H 0.3033 0.1121 0.7367 0.075 Uiso 1 1 calc R . . C6 C 0.1468(3) 0.0738(3) 0.6077(5) 0.0545(12) Uani 1 1 d . . . H6A H 0.1526 0.0116 0.6460 0.065 Uiso 1 1 calc R . . H6B H 0.0930 0.1087 0.6533 0.065 Uiso 1 1 calc R . . C7 C 0.1646(4) 0.0046(3) 0.3846(6) 0.0687(14) Uani 1 1 d . . . H7A H 0.1361 0.0081 0.2841 0.082 Uiso 1 1 calc R . . H7B H 0.1535 -0.0580 0.4153 0.082 Uiso 1 1 calc R . . C8 C 0.2950(5) 0.0314(6) 0.4206(7) 0.112(2) Uani 1 1 d . A . H8A H 0.3398 -0.0242 0.4107 0.134 Uiso 1 1 calc R . . H8B H 0.3092 0.0738 0.3481 0.134 Uiso 1 1 calc R . . C9 C 0.3455(4) 0.0710(4) 0.5485(8) 0.099(2) Uani 1 1 d D . . C10 C 0.1985(3) 0.3626(3) 0.5175(4) 0.0414(10) Uani 1 1 d . . . C11 C 0.3175(3) 0.3698(3) 0.5771(4) 0.0408(10) Uani 1 1 d . . . C12 C 0.3794(3) 0.4526(3) 0.5801(5) 0.0521(11) Uani 1 1 d . . . H12 H 0.4592 0.4562 0.6195 0.063 Uiso 1 1 calc R . . C13 C 0.3178(4) 0.5284(3) 0.5227(5) 0.0552(12) Uani 1 1 d . . . H13 H 0.3569 0.5846 0.5229 0.066 Uiso 1 1 calc R . . C14 C 0.1980(4) 0.5238(3) 0.4637(5) 0.0562(12) Uani 1 1 d . . . H14 H 0.1585 0.5768 0.4265 0.067 Uiso 1 1 calc R . . C15 C 0.1378(3) 0.4415(3) 0.4600(4) 0.0490(11) Uani 1 1 d . . . H15 H 0.0581 0.4383 0.4199 0.059 Uiso 1 1 calc R . . C16 C 0.4596(4) 0.2608(3) 0.7236(6) 0.0624(14) Uani 1 1 d . . . C17 C 0.6593(4) 0.3037(4) 0.7962(6) 0.0861(18) Uani 1 1 d . . . H17A H 0.7030 0.3614 0.8030 0.103 Uiso 1 1 calc R . . H17B H 0.6467 0.2873 0.8891 0.103 Uiso 1 1 calc R . . C18 C 0.7260(5) 0.2308(5) 0.7418(8) 0.116(2) Uani 1 1 d . . . H18A H 0.6823 0.1739 0.7358 0.134 Uiso 1 1 calc R . . H18B H 0.8006 0.2227 0.8036 0.134 Uiso 1 1 calc R . . H18C H 0.7387 0.2478 0.6502 0.134 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 0.0444(19) 0.048(2) 0.058(2) 0.0033(18) -0.0018(17) -0.0057(17) N2 0.0268(16) 0.053(2) 0.054(2) 0.0066(17) -0.0076(15) -0.0052(15) O1 0.0600(18) 0.062(2) 0.052(2) 0.0007(15) -0.0043(16) -0.0007(15) O2 0.0364(15) 0.075(2) 0.075(2) -0.0175(17) 0.0124(16) -0.0124(14) O3 0.057(2) 0.131(4) 0.125(4) 0.073(3) -0.043(2) -0.033(2) O4 0.0295(14) 0.078(2) 0.091(3) 0.0189(18) -0.0147(15) -0.0100(15) O5 0.059(5) 0.158(13) 0.072(6) -0.003(6) -0.011(4) 0.076(6) O5' 0.062(6) 0.087(7) 0.18(2) -0.059(10) 0.064(9) -0.016(5) C1 0.0268(19) 0.053(3) 0.055(3) 0.001(2) -0.0012(19) -0.0123(18) C2 0.032(2) 0.049(3) 0.057(3) -0.002(2) -0.0028(19) -0.0063(18) C3 0.0296(19) 0.043(2) 0.052(3) -0.0029(19) -0.0006(18) -0.0043(17) C4 0.033(2) 0.052(3) 0.054(3) 0.004(2) -0.0058(19) -0.0088(19) C5 0.043(2) 0.054(3) 0.078(3) 0.017(2) -0.023(2) -0.006(2) C6 0.048(2) 0.046(3) 0.063(3) 0.009(2) -0.006(2) -0.008(2) C7 0.070(3) 0.050(3) 0.087(4) 0.006(3) 0.016(3) 0.002(2) C8 0.056(3) 0.210(8) 0.074(4) -0.004(5) 0.020(3) 0.009(4) C9 0.040(3) 0.068(4) 0.180(7) -0.025(4) 0.000(4) 0.005(3) C10 0.0311(19) 0.043(2) 0.047(3) -0.0056(18) 0.0000(17) 0.0024(18) C11 0.0312(19) 0.043(2) 0.047(2) -0.0041(19) 0.0049(17) -0.0063(18) C12 0.038(2) 0.056(3) 0.061(3) -0.003(2) 0.004(2) -0.013(2) C13 0.056(3) 0.042(3) 0.066(3) 0.003(2) 0.006(2) -0.006(2) C14 0.048(2) 0.049(3) 0.068(3) -0.002(2) 0.001(2) 0.007(2) C15 0.036(2) 0.051(3) 0.056(3) -0.010(2) -0.0016(19) 0.004(2) C16 0.033(2) 0.064(3) 0.079(4) 0.017(3) -0.018(2) -0.006(2) C17 0.040(3) 0.106(5) 0.099(4) 0.008(3) -0.024(3) -0.007(3) C18 0.053(3) 0.154(6) 0.134(6) 0.028(5) 0.002(4) 0.016(4) _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 C1 1.347(5) . ? N1 C6 1.456(5) . ? N1 C7 1.457(6) . ? N2 C16 1.400(5) . ? N2 C4 1.403(5) . ? N2 C11 1.420(5) . ? O1 C1 1.234(5) . ? O2 C2 1.415(5) . ? O2 H2 0.8200 . ? O3 C16 1.191(5) . ? O4 C16 1.307(5) . ? O4 C17 1.486(5) . ? O5 C9 1.284(7) . ? O5' C9 1.304(8) . ? C1 C2 1.531(6) . ? C2 C3 1.521(5) . ? C2 H2A 0.9800 . ? C3 C4 1.359(5) . ? C3 C10 1.435(5) . ? C4 C5 1.505(6) . ? C5 C9 1.523(8) . ? C5 C6 1.529(5) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.531(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.392(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.390(5) . ? C10 C15 1.398(5) . ? C11 C12 1.393(5) . ? C12 C13 1.366(6) . ? C12 H12 0.9300 . ? C13 C14 1.396(6) . ? C13 H13 0.9300 . ? C14 C15 1.375(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.462(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C1 N1 C6 121.5(4) . . ? C1 N1 C7 118.3(4) . . ? C6 N1 C7 113.0(3) . . ? C16 N2 C4 124.5(3) . . ? C16 N2 C11 126.0(3) . . ? C4 N2 C11 108.4(3) . . ? C2 O2 H2 109.5 . . ? C16 O4 C17 115.4(4) . . ? O1 C1 N1 121.7(4) . . ? O1 C1 C2 120.2(4) . . ? N1 C1 C2 117.9(4) . . ? O2 C2 C3 115.2(3) . . ? O2 C2 C1 110.9(3) . . ? C3 C2 C1 109.3(3) . . ? O2 C2 H2A 107.0 . . ? C3 C2 H2A 107.0 . . ? C1 C2 H2A 107.0 . . ? C4 C3 C10 108.1(3) . . ? C4 C3 C2 128.8(3) . . ? C10 C3 C2 123.1(3) . . ? C3 C4 N2 108.7(3) . . ? C3 C4 C5 129.4(3) . . ? N2 C4 C5 121.7(3) . . ? C4 C5 C9 110.9(4) . . ? C4 C5 C6 110.0(3) . . ? C9 C5 C6 108.1(4) . . ? C4 C5 H5 109.3 . . ? C9 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? N1 C6 C5 110.5(4) . . ? N1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N1 C7 C8 106.8(4) . . ? N1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? N1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 122.4(5) . . ? C9 C8 H8A 106.7 . . ? C7 C8 H8A 106.7 . . ? C9 C8 H8B 106.7 . . ? C7 C8 H8B 106.7 . . ? H8A C8 H8B 106.6 . . ? O5 C9 O5' 75.3(7) . . ? O5 C9 C8 121.7(7) . . ? O5' C9 C8 97.6(8) . . ? O5 C9 C5 108.7(6) . . ? O5' C9 C5 126.1(6) . . ? C8 C9 C5 120.2(4) . . ? C11 C10 C15 119.1(3) . . ? C11 C10 C3 108.1(3) . . ? C15 C10 C3 132.7(3) . . ? C10 C11 C12 122.4(4) . . ? C10 C11 N2 106.7(3) . . ? C12 C11 N2 130.9(3) . . ? C13 C12 C11 117.1(4) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 C14 121.9(4) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 120.6(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C10 118.8(4) . . ? C14 C15 H15 120.6 . . ? C10 C15 H15 120.6 . . ? O3 C16 O4 126.0(4) . . ? O3 C16 N2 123.4(4) . . ? O4 C16 N2 110.6(4) . . ? C18 C17 O4 108.6(5) . . ? C18 C17 H17A 110.0 . . ? O4 C17 H17A 110.0 . . ? C18 C17 H17B 110.0 . . ? O4 C17 H17B 110.0 . . ? H17A C17 H17B 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C1 O1 173.7(4) . . . . ? C7 N1 C1 O1 25.6(5) . . . . ? C6 N1 C1 C2 -1.9(5) . . . . ? C7 N1 C1 C2 -150.0(3) . . . . ? O1 C1 C2 O2 120.2(4) . . . . ? N1 C1 C2 O2 -64.1(4) . . . . ? O1 C1 C2 C3 -111.7(4) . . . . ? N1 C1 C2 C3 64.0(5) . . . . ? O2 C2 C3 C4 79.1(5) . . . . ? C1 C2 C3 C4 -46.6(6) . . . . ? O2 C2 C3 C10 -104.4(4) . . . . ? C1 C2 C3 C10 129.9(4) . . . . ? C10 C3 C4 N2 -1.1(5) . . . . ? C2 C3 C4 N2 175.9(4) . . . . ? C10 C3 C4 C5 -176.1(4) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C16 N2 C4 C3 168.4(4) . . . . ? C11 N2 C4 C3 0.0(5) . . . . ? C16 N2 C4 C5 -16.1(6) . . . . ? C11 N2 C4 C5 175.5(4) . . . . ? C3 C4 C5 C9 107.9(5) . . . . ? N2 C4 C5 C9 -66.6(5) . . . . ? C3 C4 C5 C6 -11.6(7) . . . . ? N2 C4 C5 C6 173.9(4) . . . . ? C1 N1 C6 C5 -79.6(5) . . . . ? C7 N1 C6 C5 70.0(4) . . . . ? C4 C5 C6 N1 69.6(5) . . . . ? C9 C5 C6 N1 -51.7(5) . . . . ? C1 N1 C7 C8 95.8(5) . . . . ? C6 N1 C7 C8 -54.9(5) . . . . ? N1 C7 C8 C9 31.4(8) . . . . ? C7 C8 C9 O5 121.5(9) . . . . ? C7 C8 C9 O5' -161.1(8) . . . . ? C7 C8 C9 C5 -21.2(10) . . . . ? C4 C5 C9 O5 121.7(8) . . . . ? C6 C5 C9 O5 -117.6(8) . . . . ? C4 C5 C9 O5' 36.6(11) . . . . ? C6 C5 C9 O5' 157.3(10) . . . . ? C4 C5 C9 C8 -91.2(6) . . . . ? C6 C5 C9 C8 29.4(8) . . . . ? C4 C3 C10 C11 1.8(5) . . . . ? C2 C3 C10 C11 -175.3(4) . . . . ? C4 C3 C10 C15 -177.2(4) . . . . ? C2 C3 C10 C15 5.7(7) . . . . ? C15 C10 C11 C12 -1.0(6) . . . . ? C3 C10 C11 C12 179.9(4) . . . . ? C15 C10 C11 N2 177.4(3) . . . . ? C3 C10 C11 N2 -1.8(4) . . . . ? C16 N2 C11 C10 -167.1(4) . . . . ? C4 N2 C11 C10 1.2(4) . . . . ? C16 N2 C11 C12 11.0(7) . . . . ? C4 N2 C11 C12 179.3(4) . . . . ? C10 C11 C12 C13 0.7(6) . . . . ? N2 C11 C12 C13 -177.2(4) . . . . ? C11 C12 C13 C14 0.2(7) . . . . ? C12 C13 C14 C15 -0.8(7) . . . . ? C13 C14 C15 C10 0.6(7) . . . . ? C11 C10 C15 C14 0.3(6) . . . . ? C3 C10 C15 C14 179.2(4) . . . . ? C17 O4 C16 O3 -4.0(8) . . . . ? C17 O4 C16 N2 176.4(4) . . . . ? C4 N2 C16 O3 -18.8(8) . . . . ? C11 N2 C16 O3 147.6(5) . . . . ? C4 N2 C16 O4 160.8(4) . . . . ? C11 N2 C16 O4 -32.7(6) . . . . ? C16 O4 C17 C18 87.2(6) . . . . ? 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 O2 H2 O1 0.82 1.90 2.709(4) 170.8 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.320 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.056 # Attachment '- Compd 12.cif' data_cd28435 _database_code_depnum_ccdc_archive 'CCDC 790866' #TrackingRef '- Compd 12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 N2 O5' _chemical_formula_weight 356.37 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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8077(9) _cell_length_b 10.4954(12) _cell_length_c 21.518(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1763.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2348 _cell_measurement_theta_min 5.422 _cell_measurement_theta_max 43.113 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.401 _exptl_crystal_size_mid 0.232 _exptl_crystal_size_min 0.178 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8802 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10505 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2200 _reflns_number_gt 1683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^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 0.0035(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 10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2200 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 0.8234(3) 0.22704(17) 0.96237(9) 0.0663(6) Uani 1 1 d . . . O2 O 0.9802(3) 0.12338(17) 0.84085(10) 0.0793(7) Uani 1 1 d . . . O3 O 1.1940(3) 0.20727(16) 0.89396(10) 0.0687(6) Uani 1 1 d . . . O4 O 0.5872(3) 0.67235(18) 0.75185(10) 0.0769(7) Uani 1 1 d . . . O5 O 0.7354(3) 0.81667(17) 0.80440(10) 0.0676(6) Uani 1 1 d . . . N1 N 0.7340(3) 0.47590(19) 0.82168(9) 0.0459(6) Uani 1 1 d . . . N2 N 1.1570(3) 0.44198(19) 0.95022(9) 0.0385(5) Uani 1 1 d . . . C1 C 0.8147(4) 0.3165(2) 0.92771(11) 0.0434(6) Uani 1 1 d . . . C2 C 0.6774(4) 0.4140(3) 0.93127(13) 0.0580(8) Uani 1 1 d . . . H2A H 0.7236 0.4915 0.9493 0.070 Uiso 1 1 calc R . . H2B H 0.5868 0.3835 0.9583 0.070 Uiso 1 1 calc R . . C3 C 0.6026(3) 0.4439(3) 0.86698(13) 0.0617(8) Uani 1 1 d . . . H3A H 0.5388 0.3705 0.8523 0.074 Uiso 1 1 calc R . . H3B H 0.5233 0.5146 0.8706 0.074 Uiso 1 1 calc R . . C4 C 0.8543(4) 0.3723(2) 0.81575(11) 0.0444(6) Uani 1 1 d . . . H4A H 0.9387 0.3948 0.7845 0.053 Uiso 1 1 calc R . . H4B H 0.7936 0.2975 0.8010 0.053 Uiso 1 1 calc R . . C5 C 0.9495(3) 0.3373(2) 0.87713(10) 0.0356(5) Uani 1 1 d . . . C6 C 1.0642(3) 0.4461(2) 0.89569(10) 0.0333(5) Uani 1 1 d . . . C7 C 1.0915(3) 0.5599(2) 0.86666(10) 0.0360(5) Uani 1 1 d . . . C8 C 0.9900(3) 0.6182(2) 0.81482(11) 0.0418(6) Uani 1 1 d . . . H8A H 1.0170 0.5757 0.7760 0.050 Uiso 1 1 calc R . . H8B H 1.0198 0.7075 0.8106 0.050 Uiso 1 1 calc R . . C9 C 0.7981(3) 0.6055(2) 0.82840(11) 0.0402(6) Uani 1 1 d . . . H9 H 0.7812 0.6299 0.8719 0.048 Uiso 1 1 calc R . . C10 C 1.2163(3) 0.6266(2) 0.90303(12) 0.0399(6) Uani 1 1 d . . . C11 C 1.3024(4) 0.7422(2) 0.89553(14) 0.0554(7) Uani 1 1 d . . . H11 H 1.2806 0.7938 0.8613 0.066 Uiso 1 1 calc R . . C12 C 1.4194(4) 0.7782(3) 0.93950(17) 0.0737(10) Uani 1 1 d . . . H12 H 1.4797 0.8539 0.9344 0.088 Uiso 1 1 calc R . . C13 C 1.4493(4) 0.7035(3) 0.99157(18) 0.0773(10) Uani 1 1 d . . . H13 H 1.5273 0.7316 1.0212 0.093 Uiso 1 1 calc R . . C14 C 1.3673(4) 0.5895(2) 1.00055(13) 0.0575(8) Uani 1 1 d . . . H14 H 1.3878 0.5401 1.0356 0.069 Uiso 1 1 calc R . . C15 C 1.2521(3) 0.5508(2) 0.95504(11) 0.0410(6) Uani 1 1 d . . . C16 C 1.0421(4) 0.2105(2) 0.86810(11) 0.0460(6) Uani 1 1 d . . . C17 C 1.2860(5) 0.0877(3) 0.89074(17) 0.0901(12) Uani 1 1 d . . . H17A H 1.3065 0.0661 0.8480 0.135 Uiso 1 1 calc R . . H17B H 1.2190 0.0219 0.9100 0.135 Uiso 1 1 calc R . . H17C H 1.3934 0.0958 0.9121 0.135 Uiso 1 1 calc R . . C18 C 0.6935(4) 0.6981(2) 0.78909(12) 0.0471(7) Uani 1 1 d . . . C19 C 0.6463(4) 0.9184(3) 0.77402(15) 0.0756(10) Uani 1 1 d . . . H19A H 0.5251 0.9039 0.7768 0.113 Uiso 1 1 calc R . . H19B H 0.6798 0.9217 0.7311 0.113 Uiso 1 1 calc R . . H19C H 0.6742 0.9977 0.7938 0.113 Uiso 1 1 calc R . . H2 H 1.176(4) 0.376(2) 0.9739(11) 0.052(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0730(14) 0.0580(11) 0.0679(13) 0.0329(10) 0.0204(11) 0.0088(11) O2 0.1026(19) 0.0462(10) 0.0891(15) -0.0268(11) -0.0201(14) 0.0086(12) O3 0.0684(14) 0.0431(10) 0.0946(15) -0.0103(10) -0.0117(13) 0.0243(11) O4 0.0894(16) 0.0589(12) 0.0824(15) 0.0061(11) -0.0448(14) 0.0053(13) O5 0.0710(15) 0.0404(10) 0.0913(14) 0.0114(10) -0.0300(12) 0.0047(10) N1 0.0432(13) 0.0418(12) 0.0527(13) 0.0070(9) -0.0047(11) -0.0003(10) N2 0.0431(13) 0.0331(10) 0.0393(11) 0.0047(9) -0.0046(10) 0.0069(10) C1 0.0515(16) 0.0372(13) 0.0415(13) 0.0037(11) 0.0013(12) -0.0027(13) C2 0.0493(17) 0.0559(17) 0.0687(18) 0.0189(14) 0.0243(15) 0.0109(15) C3 0.0406(16) 0.0605(16) 0.084(2) 0.0233(16) 0.0028(16) 0.0020(15) C4 0.0558(17) 0.0384(13) 0.0390(13) 0.0008(11) -0.0040(12) -0.0024(12) C5 0.0439(14) 0.0282(11) 0.0347(12) 0.0020(9) -0.0001(11) 0.0009(11) C6 0.0352(13) 0.0339(11) 0.0308(11) 0.0006(10) 0.0020(10) 0.0070(10) C7 0.0348(13) 0.0341(11) 0.0390(12) 0.0052(10) 0.0062(11) 0.0042(11) C8 0.0444(16) 0.0367(12) 0.0444(14) 0.0096(11) 0.0003(12) 0.0008(12) C9 0.0432(15) 0.0401(13) 0.0373(13) 0.0038(10) -0.0045(11) 0.0040(12) C10 0.0349(14) 0.0311(11) 0.0538(15) -0.0007(11) 0.0019(12) 0.0070(11) C11 0.0414(16) 0.0372(13) 0.088(2) 0.0042(14) -0.0037(16) 0.0015(13) C12 0.058(2) 0.0386(15) 0.125(3) -0.0058(17) -0.022(2) -0.0011(15) C13 0.068(2) 0.0532(17) 0.111(3) -0.0239(18) -0.037(2) 0.0077(17) C14 0.0566(19) 0.0477(15) 0.0681(18) -0.0105(14) -0.0231(15) 0.0119(15) C15 0.0372(14) 0.0346(12) 0.0512(14) -0.0064(11) -0.0047(12) 0.0095(11) C16 0.0640(19) 0.0362(13) 0.0378(13) 0.0007(11) 0.0023(13) 0.0052(13) C17 0.103(3) 0.0581(19) 0.109(3) -0.0015(18) -0.004(2) 0.045(2) C18 0.0487(17) 0.0466(15) 0.0460(15) 0.0058(12) -0.0066(13) 0.0034(14) C19 0.078(2) 0.0491(17) 0.100(2) 0.0233(16) -0.019(2) 0.0130(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.201(3) . ? O2 C16 1.189(3) . ? O3 C16 1.311(3) . ? O3 C17 1.447(3) . ? O4 C18 1.185(3) . ? O5 C18 1.328(3) . ? O5 C19 1.432(3) . ? N1 C4 1.443(3) . ? N1 C3 1.455(3) . ? N1 C9 1.457(3) . ? N2 C15 1.366(3) . ? N2 C6 1.380(3) . ? N2 H2 0.87(2) . ? C1 C2 1.484(4) . ? C1 C5 1.530(3) . ? C2 C3 1.534(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.559(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.504(3) . ? C5 C16 1.527(3) . ? C6 C7 1.365(3) . ? C7 C10 1.433(3) . ? C7 C8 1.499(3) . ? C8 C9 1.532(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C18 1.525(3) . ? C9 H9 0.9800 . ? C10 C11 1.397(3) . ? C10 C15 1.401(3) . ? C11 C12 1.369(4) . ? C11 H11 0.9300 . ? C12 C13 1.387(5) . ? C12 H12 0.9300 . ? C13 C14 1.371(4) . ? C13 H13 0.9300 . ? C14 C15 1.390(3) . ? C14 H14 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C16 O3 C17 116.8(2) . . ? C18 O5 C19 117.7(2) . . ? C4 N1 C3 110.14(19) . . ? C4 N1 C9 119.3(2) . . ? C3 N1 C9 113.1(2) . . ? C15 N2 C6 108.92(19) . . ? C15 N2 H2 122.0(18) . . ? C6 N2 H2 127.4(17) . . ? O1 C1 C2 123.2(2) . . ? O1 C1 C5 121.0(2) . . ? C2 C1 C5 115.79(19) . . ? C1 C2 C3 111.7(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N1 C3 C2 112.5(2) . . ? N1 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? N1 C4 C5 114.37(18) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C16 114.4(2) . . ? C6 C5 C1 109.20(18) . . ? C16 C5 C1 106.95(18) . . ? C6 C5 C4 109.28(17) . . ? C16 C5 C4 108.83(18) . . ? C1 C5 C4 108.0(2) . . ? C7 C6 N2 109.5(2) . . ? C7 C6 C5 129.5(2) . . ? N2 C6 C5 121.00(18) . . ? C6 C7 C10 106.5(2) . . ? C6 C7 C8 128.0(2) . . ? C10 C7 C8 124.5(2) . . ? C7 C8 C9 109.85(19) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N1 C9 C18 110.8(2) . . ? N1 C9 C8 113.5(2) . . ? C18 C9 C8 111.3(2) . . ? N1 C9 H9 107.0 . . ? C18 C9 H9 107.0 . . ? C8 C9 H9 107.0 . . ? C11 C10 C15 119.3(2) . . ? C11 C10 C7 133.5(2) . . ? C15 C10 C7 107.1(2) . . ? C12 C11 C10 118.8(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 121.9(3) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 117.3(3) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? N2 C15 C14 130.5(2) . . ? N2 C15 C10 107.8(2) . . ? C14 C15 C10 121.7(2) . . ? O2 C16 O3 123.9(2) . . ? O2 C16 C5 122.7(3) . . ? O3 C16 C5 113.4(2) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 O5 123.6(2) . . ? O4 C18 C9 127.2(2) . . ? O5 C18 C9 109.1(2) . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -133.9(3) . . . . ? C5 C1 C2 C3 47.1(3) . . . . ? C4 N1 C3 C2 58.4(3) . . . . ? C9 N1 C3 C2 -77.8(3) . . . . ? C1 C2 C3 N1 -52.2(3) . . . . ? C3 N1 C4 C5 -60.0(3) . . . . ? C9 N1 C4 C5 73.2(3) . . . . ? O1 C1 C5 C6 -106.1(3) . . . . ? C2 C1 C5 C6 72.9(3) . . . . ? O1 C1 C5 C16 18.2(3) . . . . ? C2 C1 C5 C16 -162.8(2) . . . . ? O1 C1 C5 C4 135.1(3) . . . . ? C2 C1 C5 C4 -45.8(3) . . . . ? N1 C4 C5 C6 -66.4(3) . . . . ? N1 C4 C5 C16 168.0(2) . . . . ? N1 C4 C5 C1 52.3(3) . . . . ? C15 N2 C6 C7 -3.2(3) . . . . ? C15 N2 C6 C5 178.8(2) . . . . ? C16 C5 C6 C7 121.6(3) . . . . ? C1 C5 C6 C7 -118.6(2) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C16 C5 C6 N2 -60.8(3) . . . . ? C1 C5 C6 N2 59.0(3) . . . . ? C4 C5 C6 N2 176.9(2) . . . . ? N2 C6 C7 C10 3.8(2) . . . . ? C5 C6 C7 C10 -178.4(2) . . . . ? N2 C6 C7 C8 -165.0(2) . . . . ? C5 C6 C7 C8 12.9(4) . . . . ? C6 C7 C8 C9 44.9(3) . . . . ? C10 C7 C8 C9 -122.0(2) . . . . ? C4 N1 C9 C18 138.0(2) . . . . ? C3 N1 C9 C18 -90.1(2) . . . . ? C4 N1 C9 C8 12.0(3) . . . . ? C3 N1 C9 C8 143.9(2) . . . . ? C7 C8 C9 N1 -72.4(3) . . . . ? C7 C8 C9 C18 161.8(2) . . . . ? C6 C7 C10 C11 175.6(3) . . . . ? C8 C7 C10 C11 -15.1(4) . . . . ? C6 C7 C10 C15 -3.1(2) . . . . ? C8 C7 C10 C15 166.2(2) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C7 C10 C11 C12 -178.7(3) . . . . ? C10 C11 C12 C13 -1.7(5) . . . . ? C11 C12 C13 C14 1.8(5) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C6 N2 C15 C14 -178.7(2) . . . . ? C6 N2 C15 C10 1.1(3) . . . . ? C13 C14 C15 N2 177.7(3) . . . . ? C13 C14 C15 C10 -2.1(4) . . . . ? C11 C10 C15 N2 -177.7(2) . . . . ? C7 C10 C15 N2 1.2(3) . . . . ? C11 C10 C15 C14 2.1(4) . . . . ? C7 C10 C15 C14 -179.0(2) . . . . ? C17 O3 C16 O2 -2.8(4) . . . . ? C17 O3 C16 C5 176.4(2) . . . . ? C6 C5 C16 O2 -163.1(2) . . . . ? C1 C5 C16 O2 75.9(3) . . . . ? C4 C5 C16 O2 -40.5(3) . . . . ? C6 C5 C16 O3 17.8(3) . . . . ? C1 C5 C16 O3 -103.3(2) . . . . ? C4 C5 C16 O3 140.3(2) . . . . ? C19 O5 C18 O4 0.1(4) . . . . ? C19 O5 C18 C9 -177.8(2) . . . . ? N1 C9 C18 O4 -8.6(4) . . . . ? C8 C9 C18 O4 118.7(3) . . . . ? N1 C9 C18 O5 169.3(2) . . . . ? C8 C9 C18 O5 -63.4(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 N2 H2 O1 0.87(2) 2.09(3) 2.893(3) 152(2) 4_557 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.132 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.029