# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email aco48@uni-koeln.de _publ_contact_author_name 'Jorg-M. Neudorfl' loop_ _publ_author_name 'Robert Fichtler' 'Jorg-M. Neudorfl' 'Axel Jacobi von Wangelin' data_rob208n _database_code_depnum_ccdc_archive 'CCDC 832706' #TrackingRef 'rob208.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H37 N O6' _chemical_formula_sum 'C26 H37 N O6' _chemical_formula_weight 459.57 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/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 13.7746(9) _cell_length_b 11.7176(8) _cell_length_c 19.9018(12) _cell_angle_alpha 90.00 _cell_angle_beta 127.838(4) _cell_angle_gamma 90.00 _cell_volume 2536.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11444 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11444 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.1266 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5508 _reflns_number_gt 2887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0275P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5508 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _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 0.59280(10) -0.09975(10) -0.02614(7) 0.0254(3) Uani 1 1 d . . . O2 O 0.44695(10) -0.21538(10) -0.04125(7) 0.0280(3) Uani 1 1 d . . . O3 O 0.56046(9) -0.41552(9) -0.09644(6) 0.0212(3) Uani 1 1 d . . . O4 O 0.37837(10) -0.49772(10) -0.14941(7) 0.0258(3) Uani 1 1 d . . . O5 O 0.21584(9) -0.58672(9) -0.38474(7) 0.0227(3) Uani 1 1 d . . . O6 O 0.42005(9) -0.55843(9) -0.29116(7) 0.0223(3) Uani 1 1 d . . . N1 N 0.44763(12) -0.17276(12) -0.15259(8) 0.0186(3) Uani 1 1 d . . . H1A H 0.4889(13) -0.1395(13) -0.1664(9) 0.020(5) Uiso 1 1 d . . . C1 C 0.49105(15) -0.16870(14) -0.07093(10) 0.0206(4) Uani 1 1 d . . . C2 C 0.34263(13) -0.24323(13) -0.21579(9) 0.0174(4) Uani 1 1 d . . . H2 H 0.2996 -0.2658 -0.1917 0.021 Uiso 1 1 calc R . . C3 C 0.38699(14) -0.35397(13) -0.23175(9) 0.0171(4) Uani 1 1 d . . . H3 H 0.4525 -0.3348 -0.2373 0.021 Uiso 1 1 calc R . . C4 C 0.43971(15) -0.43205(14) -0.15600(10) 0.0196(4) Uani 1 1 d . . . C5 C 0.61653(14) -0.47572(15) -0.01551(10) 0.0241(4) Uani 1 1 d . . . H5A H 0.5921 -0.5571 -0.0261 0.029 Uiso 1 1 calc R . . H5B H 0.5897 -0.4411 0.0160 0.029 Uiso 1 1 calc R . . C6 C 0.75346(14) -0.46476(15) 0.03469(10) 0.0297(5) Uani 1 1 d . . . H6A H 0.7786 -0.4989 0.0026 0.044 Uiso 1 1 calc R . . H6B H 0.7946 -0.5044 0.0893 0.044 Uiso 1 1 calc R . . H6C H 0.7764 -0.3839 0.0450 0.044 Uiso 1 1 calc R . . C7 C 0.28032(14) -0.41148(13) -0.31292(9) 0.0167(4) Uani 1 1 d . . . H7 H 0.2152 -0.4257 -0.3061 0.020 Uiso 1 1 calc R . . C8 C 0.31573(15) -0.52548(14) -0.32648(10) 0.0175(4) Uani 1 1 d . . . C9 C 0.23746(14) -0.69800(13) -0.40597(10) 0.0244(4) Uani 1 1 d . . . H9A H 0.2943 -0.7437 -0.3538 0.029 Uiso 1 1 calc R . . H9B H 0.2738 -0.6893 -0.4359 0.029 Uiso 1 1 calc R . . C10 C 0.11378(14) -0.75499(14) -0.46281(11) 0.0304(5) Uani 1 1 d . . . H10A H 0.0782 -0.7611 -0.4328 0.046 Uiso 1 1 calc R . . H10B H 0.1233 -0.8314 -0.4780 0.046 Uiso 1 1 calc R . . H10C H 0.0592 -0.7095 -0.5146 0.046 Uiso 1 1 calc R . . C11 C 0.22217(14) -0.33509(13) -0.39283(10) 0.0175(4) Uani 1 1 d . . . H11 H 0.1383 -0.3670 -0.4367 0.021 Uiso 1 1 calc R . . C12 C 0.20233(14) -0.21759(13) -0.37314(10) 0.0187(4) Uani 1 1 d . . . H12 H 0.1488 -0.1688 -0.4203 0.022 Uiso 1 1 calc R . . C13 C 0.25205(14) -0.17498(13) -0.29646(10) 0.0168(4) Uani 1 1 d . . . C14 C 0.21934(14) -0.05694(13) -0.28362(10) 0.0196(4) Uani 1 1 d . . . H14 H 0.2409 -0.0558 -0.2256 0.024 Uiso 1 1 calc R . . C15 C 0.29430(14) 0.03681(13) -0.28584(11) 0.0284(5) Uani 1 1 d . . . H15A H 0.2764 0.0373 -0.3417 0.043 Uiso 1 1 calc R . . H15B H 0.3821 0.0223 -0.2416 0.043 Uiso 1 1 calc R . . H15C H 0.2725 0.1109 -0.2756 0.043 Uiso 1 1 calc R . . C16 C 0.08214(14) -0.02924(14) -0.34751(10) 0.0264(4) Uani 1 1 d . . . H16A H 0.0599 -0.0205 -0.4044 0.040 Uiso 1 1 calc R . . H16B H 0.0647 0.0419 -0.3309 0.040 Uiso 1 1 calc R . . H16C H 0.0340 -0.0914 -0.3481 0.040 Uiso 1 1 calc R . . C17 C 0.28771(14) -0.33518(14) -0.43422(10) 0.0221(4) Uani 1 1 d . . . H17 H 0.3061 -0.4164 -0.4381 0.027 Uiso 1 1 calc R . . C18 C 0.40911(15) -0.26976(15) -0.38498(10) 0.0301(5) Uani 1 1 d . . . H18A H 0.4374 -0.2642 -0.4196 0.045 Uiso 1 1 calc R . . H18B H 0.4708 -0.3102 -0.3319 0.045 Uiso 1 1 calc R . . H18C H 0.3970 -0.1929 -0.3718 0.045 Uiso 1 1 calc R . . C19 C 0.20032(15) -0.28895(15) -0.52528(10) 0.0309(5) Uani 1 1 d . . . H19A H 0.1802 -0.2092 -0.5238 0.046 Uiso 1 1 calc R . . H19B H 0.1248 -0.3345 -0.5578 0.046 Uiso 1 1 calc R . . H19C H 0.2402 -0.2936 -0.5524 0.046 Uiso 1 1 calc R . . C20 C 0.64376(15) -0.07509(15) 0.06141(10) 0.0290(5) Uani 1 1 d . . . H20A H 0.5814 -0.0923 0.0698 0.035 Uiso 1 1 calc R . . H20B H 0.6637 0.0072 0.0728 0.035 Uiso 1 1 calc R . . C21 C 0.75789(15) -0.14385(15) 0.12348(10) 0.0225(4) Uani 1 1 d . . . C22 C 0.75368(18) -0.24057(15) 0.16091(11) 0.0343(5) Uani 1 1 d . . . H22 H 0.6771 -0.2658 0.1458 0.041 Uiso 1 1 calc R . . C23 C 0.85857(19) -0.30111(18) 0.21971(12) 0.0450(6) Uani 1 1 d . . . H23 H 0.8541 -0.3671 0.2454 0.054 Uiso 1 1 calc R . . C24 C 0.9696(2) -0.26676(18) 0.24152(12) 0.0479(6) Uani 1 1 d . . . H24 H 1.0419 -0.3088 0.2823 0.057 Uiso 1 1 calc R . . C25 C 0.97617(17) -0.17067(19) 0.20405(12) 0.0492(6) Uani 1 1 d . . . H25 H 1.0529 -0.1471 0.2185 0.059 Uiso 1 1 calc R . . C26 C 0.86951(16) -0.10843(17) 0.14486(11) 0.0378(5) Uani 1 1 d . . . H26 H 0.8737 -0.0420 0.1194 0.045 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 0.0212(7) 0.0325(7) 0.0164(6) -0.0081(6) 0.0084(6) -0.0059(6) O2 0.0314(7) 0.0375(8) 0.0212(7) -0.0004(6) 0.0192(6) -0.0035(6) O3 0.0188(6) 0.0250(7) 0.0160(6) 0.0037(5) 0.0087(5) 0.0002(5) O4 0.0250(7) 0.0289(8) 0.0231(7) 0.0021(6) 0.0145(6) -0.0060(6) O5 0.0189(6) 0.0165(7) 0.0269(7) -0.0054(6) 0.0111(6) -0.0019(5) O6 0.0177(7) 0.0242(7) 0.0220(7) -0.0011(6) 0.0108(6) 0.0014(6) N1 0.0181(8) 0.0229(9) 0.0150(8) -0.0011(7) 0.0102(7) -0.0042(7) C1 0.0187(10) 0.0207(10) 0.0192(10) -0.0009(9) 0.0100(9) 0.0035(9) C2 0.0162(9) 0.0203(10) 0.0165(9) -0.0037(8) 0.0105(8) -0.0058(8) C3 0.0172(9) 0.0190(10) 0.0169(9) 0.0008(8) 0.0114(8) 0.0001(8) C4 0.0212(10) 0.0198(10) 0.0206(10) -0.0038(8) 0.0141(9) -0.0003(8) C5 0.0253(10) 0.0260(11) 0.0169(9) 0.0058(8) 0.0109(9) 0.0014(9) C6 0.0268(10) 0.0331(12) 0.0225(10) 0.0058(9) 0.0117(9) 0.0042(9) C7 0.0156(9) 0.0172(10) 0.0184(9) -0.0014(8) 0.0109(8) -0.0023(8) C8 0.0207(10) 0.0203(10) 0.0132(9) 0.0020(8) 0.0111(8) -0.0019(9) C9 0.0257(10) 0.0173(10) 0.0289(10) -0.0049(9) 0.0161(9) 0.0002(8) C10 0.0253(11) 0.0255(11) 0.0359(11) -0.0095(9) 0.0164(10) -0.0049(9) C11 0.0160(9) 0.0178(10) 0.0147(9) -0.0019(8) 0.0075(8) 0.0005(8) C12 0.0159(9) 0.0194(10) 0.0190(9) 0.0038(8) 0.0098(8) 0.0034(8) C13 0.0142(9) 0.0181(10) 0.0190(9) -0.0001(8) 0.0107(8) -0.0015(8) C14 0.0201(9) 0.0201(10) 0.0174(9) -0.0025(8) 0.0109(8) -0.0005(8) C15 0.0287(11) 0.0194(10) 0.0364(11) -0.0011(9) 0.0196(10) 0.0007(9) C16 0.0248(10) 0.0231(11) 0.0304(10) -0.0014(9) 0.0165(9) 0.0037(9) C17 0.0277(10) 0.0224(10) 0.0180(9) 0.0028(8) 0.0149(9) 0.0067(9) C18 0.0278(10) 0.0438(13) 0.0238(10) 0.0043(9) 0.0184(9) 0.0031(9) C19 0.0349(11) 0.0357(12) 0.0205(10) 0.0012(9) 0.0162(9) 0.0027(9) C20 0.0279(10) 0.0346(12) 0.0189(10) -0.0110(9) 0.0115(9) -0.0011(9) C21 0.0228(10) 0.0254(11) 0.0149(9) -0.0050(8) 0.0093(9) 0.0017(9) C22 0.0396(12) 0.0330(12) 0.0295(11) -0.0030(10) 0.0208(11) -0.0009(10) C23 0.0557(15) 0.0438(14) 0.0355(13) 0.0046(11) 0.0280(12) 0.0134(12) C24 0.0488(15) 0.0620(17) 0.0227(12) 0.0091(11) 0.0168(11) 0.0300(13) C25 0.0246(12) 0.0819(18) 0.0358(13) 0.0000(13) 0.0158(11) 0.0075(12) C26 0.0334(12) 0.0481(14) 0.0314(11) 0.0030(10) 0.0196(10) -0.0010(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 C1 1.3707(19) . ? O1 C20 1.4531(18) . ? O2 C1 1.2072(19) . ? O3 C4 1.3380(18) . ? O3 C5 1.4704(18) . ? O4 C4 1.2079(18) . ? O5 C8 1.3399(18) . ? O5 C9 1.4567(18) . ? O6 C8 1.2119(17) . ? N1 C1 1.345(2) . ? N1 C2 1.4573(19) . ? N1 H1A 0.862(15) . ? C2 C13 1.522(2) . ? C2 C3 1.548(2) . ? C2 H2 1.0000 . ? C3 C4 1.515(2) . ? C3 C7 1.520(2) . ? C3 H3 1.0000 . ? C5 C6 1.503(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.502(2) . ? C7 C11 1.552(2) . ? C7 H7 1.0000 . ? C9 C10 1.505(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.502(2) . ? C11 C17 1.551(2) . ? C11 H11 1.0000 . ? C12 C13 1.329(2) . ? C12 H12 0.9500 . ? C13 C14 1.524(2) . ? C14 C15 1.527(2) . ? C14 C16 1.531(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.528(2) . ? C17 C19 1.533(2) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.505(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.377(2) . ? C21 C26 1.384(2) . ? C22 C23 1.373(2) . ? C22 H22 0.9500 . ? C23 C24 1.369(3) . ? C23 H23 0.9500 . ? C24 C25 1.384(3) . ? C24 H24 0.9500 . ? C25 C26 1.398(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C20 116.50(13) . . ? C4 O3 C5 115.67(12) . . ? C8 O5 C9 116.50(12) . . ? C1 N1 C2 122.23(15) . . ? C1 N1 H1A 118.6(10) . . ? C2 N1 H1A 118.7(10) . . ? O2 C1 N1 126.23(17) . . ? O2 C1 O1 124.71(16) . . ? N1 C1 O1 109.04(15) . . ? N1 C2 C13 110.49(13) . . ? N1 C2 C3 110.15(12) . . ? C13 C2 C3 113.29(13) . . ? N1 C2 H2 107.6 . . ? C13 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C4 C3 C7 110.53(13) . . ? C4 C3 C2 108.10(13) . . ? C7 C3 C2 110.11(12) . . ? C4 C3 H3 109.4 . . ? C7 C3 H3 109.4 . . ? C2 C3 H3 109.4 . . ? O4 C4 O3 124.62(15) . . ? O4 C4 C3 123.55(15) . . ? O3 C4 C3 111.77(14) . . ? O3 C5 C6 106.79(13) . . ? O3 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? O3 C5 H5B 110.4 . . ? C6 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C3 112.11(13) . . ? C8 C7 C11 110.43(13) . . ? C3 C7 C11 112.84(13) . . ? C8 C7 H7 107.0 . . ? C3 C7 H7 107.0 . . ? C11 C7 H7 107.0 . . ? O6 C8 O5 123.66(15) . . ? O6 C8 C7 125.39(15) . . ? O5 C8 C7 110.94(13) . . ? O5 C9 C10 106.07(13) . . ? O5 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? O5 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C17 113.42(13) . . ? C12 C11 C7 108.88(13) . . ? C17 C11 C7 116.17(13) . . ? C12 C11 H11 105.8 . . ? C17 C11 H11 105.8 . . ? C7 C11 H11 105.8 . . ? C13 C12 C11 126.60(15) . . ? C13 C12 H12 116.7 . . ? C11 C12 H12 116.7 . . ? C12 C13 C2 121.71(15) . . ? C12 C13 C14 122.45(14) . . ? C2 C13 C14 115.82(13) . . ? C13 C14 C15 111.92(13) . . ? C13 C14 C16 113.22(13) . . ? C15 C14 C16 109.60(13) . . ? C13 C14 H14 107.3 . . ? C15 C14 H14 107.3 . . ? C16 C14 H14 107.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 109.74(14) . . ? C18 C17 C11 115.06(13) . . ? C19 C17 C11 109.68(13) . . ? C18 C17 H17 107.3 . . ? C19 C17 H17 107.3 . . ? C11 C17 H17 107.3 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 C21 111.77(14) . . ? O1 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? O1 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C22 C21 C26 119.22(17) . . ? C22 C21 C20 121.02(17) . . ? C26 C21 C20 119.74(17) . . ? C23 C22 C21 120.98(19) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.89(19) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C26 119.7(2) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 119.84(19) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? 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 C2 N1 C1 O2 -4.4(3) . . . . ? C2 N1 C1 O1 177.32(13) . . . . ? C20 O1 C1 O2 -5.1(2) . . . . ? C20 O1 C1 N1 173.23(13) . . . . ? C1 N1 C2 C13 132.82(15) . . . . ? C1 N1 C2 C3 -101.26(17) . . . . ? N1 C2 C3 C4 74.41(16) . . . . ? C13 C2 C3 C4 -161.27(13) . . . . ? N1 C2 C3 C7 -164.75(13) . . . . ? C13 C2 C3 C7 -40.43(18) . . . . ? C5 O3 C4 O4 -5.5(2) . . . . ? C5 O3 C4 C3 171.76(13) . . . . ? C7 C3 C4 O4 -34.2(2) . . . . ? C2 C3 C4 O4 86.36(19) . . . . ? C7 C3 C4 O3 148.50(13) . . . . ? C2 C3 C4 O3 -90.93(15) . . . . ? C4 O3 C5 C6 168.99(13) . . . . ? C4 C3 C7 C8 -54.76(18) . . . . ? C2 C3 C7 C8 -174.13(13) . . . . ? C4 C3 C7 C11 179.79(13) . . . . ? C2 C3 C7 C11 60.42(17) . . . . ? C9 O5 C8 O6 -0.8(2) . . . . ? C9 O5 C8 C7 178.04(13) . . . . ? C3 C7 C8 O6 -16.9(2) . . . . ? C11 C7 C8 O6 109.81(17) . . . . ? C3 C7 C8 O5 164.21(13) . . . . ? C11 C7 C8 O5 -69.03(17) . . . . ? C8 O5 C9 C10 172.69(14) . . . . ? C8 C7 C11 C12 -173.12(13) . . . . ? C3 C7 C11 C12 -46.76(17) . . . . ? C8 C7 C11 C17 -43.62(18) . . . . ? C3 C7 C11 C17 82.74(17) . . . . ? C17 C11 C12 C13 -115.36(18) . . . . ? C7 C11 C12 C13 15.6(2) . . . . ? C11 C12 C13 C2 2.1(3) . . . . ? C11 C12 C13 C14 -175.90(15) . . . . ? N1 C2 C13 C12 134.62(16) . . . . ? C3 C2 C13 C12 10.5(2) . . . . ? N1 C2 C13 C14 -47.25(18) . . . . ? C3 C2 C13 C14 -171.39(13) . . . . ? C12 C13 C14 C15 -83.98(19) . . . . ? C2 C13 C14 C15 97.89(16) . . . . ? C12 C13 C14 C16 40.5(2) . . . . ? C2 C13 C14 C16 -137.62(14) . . . . ? C12 C11 C17 C18 53.61(18) . . . . ? C7 C11 C17 C18 -73.67(18) . . . . ? C12 C11 C17 C19 -70.67(17) . . . . ? C7 C11 C17 C19 162.05(14) . . . . ? C1 O1 C20 C21 103.17(17) . . . . ? O1 C20 C21 C22 -100.44(19) . . . . ? O1 C20 C21 C26 80.9(2) . . . . ? C26 C21 C22 C23 0.9(3) . . . . ? C20 C21 C22 C23 -177.77(16) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 0.8(3) . . . . ? C22 C21 C26 C25 -0.2(3) . . . . ? C20 C21 C26 C25 178.48(17) . . . . ? C24 C25 C26 C21 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.200 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.046 # Attachment 'rob208a.cif' data_rob208a _database_code_depnum_ccdc_archive 'CCDC 832707' #TrackingRef 'rob208a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H37 N O6' _chemical_formula_sum 'C26 H37 N O6' _chemical_formula_weight 459.57 _chemical_absolute_configuration unk 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 10.4445(10) _cell_length_b 14.899(2) _cell_length_c 16.596(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2582.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11965 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .03 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11965 _diffrn_reflns_av_R_equivalents 0.1433 _diffrn_reflns_av_sigmaI/netI 0.1407 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2590 _reflns_number_gt 1275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 2590 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1486 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.002 _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 -0.7585(3) -0.0045(2) 0.1332(2) 0.0387(10) Uani 1 1 d . . . O2 O -0.5598(3) -0.0573(2) 0.1632(2) 0.0392(10) Uani 1 1 d . . . O3 O -0.4171(3) -0.0012(3) 0.0003(2) 0.0462(11) Uani 1 1 d . . . O4 O -0.5062(4) 0.1052(3) -0.0739(3) 0.0640(13) Uani 1 1 d . . . O5 O -0.4876(4) 0.3028(3) -0.0979(2) 0.0447(11) Uani 1 1 d . . . O6 O -0.2825(4) 0.2643(2) -0.0766(2) 0.0431(11) Uani 1 1 d . . . N1 N -0.5941(4) 0.0879(3) 0.1236(3) 0.0326(12) Uani 1 1 d . . . H1A H -0.657(4) 0.127(3) 0.120(3) 0.038(17) Uiso 1 1 d . . . C1 C -0.6289(5) 0.0037(4) 0.1419(3) 0.0333(14) Uani 1 1 d . . . C2 C -0.4600(4) 0.1180(4) 0.1305(4) 0.0361(15) Uani 1 1 d . . . H2 H -0.4088 0.0655 0.1497 0.043 Uiso 1 1 calc R . . C3 C -0.4042(5) 0.1467(4) 0.0493(3) 0.0390(15) Uani 1 1 d . . . H3 H -0.3089 0.1430 0.0533 0.047 Uiso 1 1 calc R . . C4 C -0.4465(5) 0.0824(4) -0.0160(4) 0.0363(15) Uani 1 1 d . . . C5 C -0.4697(7) -0.0686(4) -0.0546(4) 0.073(2) Uani 1 1 d . . . H5A H -0.4302 -0.0620 -0.1085 0.088 Uiso 1 1 calc R . . H5B H -0.5633 -0.0599 -0.0602 0.088 Uiso 1 1 calc R . . C6 C -0.4431(7) -0.1595(5) -0.0223(4) 0.085(2) Uani 1 1 d . . . H6A H -0.3504 -0.1681 -0.0178 0.128 Uiso 1 1 calc R . . H6B H -0.4788 -0.2047 -0.0588 0.128 Uiso 1 1 calc R . . H6C H -0.4825 -0.1656 0.0310 0.128 Uiso 1 1 calc R . . C7 C -0.4390(5) 0.2428(4) 0.0308(3) 0.0394(16) Uani 1 1 d . . . H7 H -0.5342 0.2494 0.0332 0.047 Uiso 1 1 calc R . . C8 C -0.3927(6) 0.2698(4) -0.0535(4) 0.0393(16) Uani 1 1 d . . . C9 C -0.4567(5) 0.3241(4) -0.1810(3) 0.0429(17) Uani 1 1 d . . . H9A H -0.4075 0.2746 -0.2061 0.051 Uiso 1 1 calc R . . H9B H -0.4051 0.3798 -0.1840 0.051 Uiso 1 1 calc R . . C10 C -0.5822(5) 0.3364(4) -0.2228(4) 0.0581(19) Uani 1 1 d . . . H10A H -0.6344 0.2823 -0.2160 0.087 Uiso 1 1 calc R . . H10B H -0.5673 0.3470 -0.2804 0.087 Uiso 1 1 calc R . . H10C H -0.6271 0.3880 -0.1996 0.087 Uiso 1 1 calc R . . C11 C -0.3782(5) 0.3063(4) 0.0924(3) 0.0348(14) Uani 1 1 d . . . H11 H -0.2832 0.3023 0.0859 0.042 Uiso 1 1 calc R . . C12 C -0.4104(4) 0.2737(4) 0.1752(3) 0.0365(15) Uani 1 1 d . . . H12 H -0.4025 0.3156 0.2181 0.044 Uiso 1 1 calc R . . C13 C -0.4498(4) 0.1901(4) 0.1942(3) 0.0306(14) Uani 1 1 d . . . C14 C -0.4900(5) 0.1642(4) 0.2787(3) 0.0348(15) Uani 1 1 d . . . H14 H -0.5142 0.0993 0.2775 0.042 Uiso 1 1 calc R . . C15 C -0.3835(5) 0.1747(4) 0.3398(3) 0.0575(19) Uani 1 1 d . . . H15A H -0.3107 0.1371 0.3241 0.086 Uiso 1 1 calc R . . H15B H -0.4143 0.1562 0.3930 0.086 Uiso 1 1 calc R . . H15C H -0.3565 0.2377 0.3418 0.086 Uiso 1 1 calc R . . C16 C -0.6075(6) 0.2167(4) 0.3060(4) 0.0564(19) Uani 1 1 d . . . H16A H -0.5860 0.2806 0.3098 0.085 Uiso 1 1 calc R . . H16B H -0.6352 0.1948 0.3589 0.085 Uiso 1 1 calc R . . H16C H -0.6768 0.2085 0.2669 0.085 Uiso 1 1 calc R . . C17 C -0.4171(5) 0.4052(4) 0.0792(4) 0.0414(16) Uani 1 1 d . . . H17 H -0.4074 0.4186 0.0205 0.050 Uiso 1 1 calc R . . C18 C -0.3306(5) 0.4683(3) 0.1243(4) 0.0517(18) Uani 1 1 d . . . H18A H -0.3453 0.4618 0.1823 0.077 Uiso 1 1 calc R . . H18B H -0.3491 0.5302 0.1080 0.077 Uiso 1 1 calc R . . H18C H -0.2412 0.4541 0.1119 0.077 Uiso 1 1 calc R . . C19 C -0.5576(5) 0.4231(4) 0.1019(4) 0.0578(19) Uani 1 1 d . . . H19A H -0.5695 0.4127 0.1598 0.087 Uiso 1 1 calc R . . H19B H -0.6134 0.3826 0.0714 0.087 Uiso 1 1 calc R . . H19C H -0.5795 0.4855 0.0891 0.087 Uiso 1 1 calc R . . C20 C -0.8063(4) -0.0950(4) 0.1494(4) 0.0452(17) Uani 1 1 d . . . H20A H -0.7699 -0.1183 0.2004 0.054 Uiso 1 1 calc R . . H20B H -0.7821 -0.1362 0.1051 0.054 Uiso 1 1 calc R . . C21 C -0.9499(5) -0.0877(4) 0.1556(4) 0.0346(15) Uani 1 1 d . . . C22 C -1.0102(5) -0.0951(4) 0.2282(4) 0.0462(17) Uani 1 1 d . . . H22 H -0.9610 -0.1032 0.2757 0.055 Uiso 1 1 calc R . . C23 C -1.1438(6) -0.0908(4) 0.2334(5) 0.061(2) Uani 1 1 d . . . H23 H -1.1856 -0.0968 0.2839 0.073 Uiso 1 1 calc R . . C24 C -1.2145(6) -0.0777(4) 0.1635(6) 0.069(2) Uani 1 1 d . . . H24 H -1.3053 -0.0749 0.1658 0.083 Uiso 1 1 calc R . . C25 C -1.1528(6) -0.0689(4) 0.0911(5) 0.069(2) Uani 1 1 d . . . H25 H -1.2014 -0.0585 0.0437 0.083 Uiso 1 1 calc R . . C26 C -1.0210(5) -0.0748(4) 0.0861(4) 0.0543(18) Uani 1 1 d . . . H26 H -0.9794 -0.0700 0.0353 0.065 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 0.0267(19) 0.036(2) 0.053(3) 0.003(2) -0.0018(19) -0.0027(17) O2 0.0359(19) 0.033(3) 0.049(3) 0.008(2) -0.0011(19) 0.0036(19) O3 0.055(2) 0.036(3) 0.047(3) -0.004(2) -0.005(2) 0.006(2) O4 0.093(3) 0.054(3) 0.046(3) -0.001(3) -0.022(3) 0.003(3) O5 0.046(2) 0.062(3) 0.027(3) 0.010(2) 0.001(2) -0.010(2) O6 0.045(2) 0.043(3) 0.041(3) 0.002(2) 0.001(2) 0.0022(19) N1 0.030(3) 0.024(3) 0.044(3) 0.004(3) -0.005(2) 0.008(2) C1 0.041(4) 0.033(4) 0.025(4) -0.005(4) -0.003(3) 0.002(3) C2 0.031(3) 0.033(4) 0.044(4) 0.011(3) 0.000(3) -0.001(2) C3 0.040(3) 0.040(4) 0.037(4) -0.001(3) 0.001(3) 0.001(3) C4 0.041(3) 0.037(4) 0.031(4) 0.011(4) -0.008(3) -0.004(3) C5 0.134(6) 0.034(4) 0.051(5) -0.018(4) -0.014(5) -0.005(4) C6 0.114(6) 0.070(6) 0.072(6) -0.011(5) -0.004(5) -0.004(5) C7 0.053(4) 0.037(4) 0.027(4) 0.002(3) 0.006(3) -0.004(3) C8 0.045(4) 0.034(4) 0.038(4) 0.003(3) -0.008(4) -0.008(3) C9 0.047(4) 0.044(4) 0.038(4) 0.006(3) 0.003(3) -0.010(3) C10 0.054(4) 0.067(5) 0.054(5) -0.008(4) -0.014(4) 0.002(4) C11 0.045(3) 0.034(4) 0.026(4) 0.003(3) -0.004(3) -0.014(3) C12 0.034(3) 0.042(4) 0.034(4) -0.001(3) -0.008(3) -0.002(3) C13 0.026(3) 0.039(4) 0.027(4) -0.002(3) -0.001(3) 0.001(3) C14 0.032(3) 0.035(4) 0.037(4) -0.001(3) 0.000(3) 0.002(3) C15 0.054(4) 0.080(5) 0.039(4) 0.020(4) -0.007(3) -0.017(4) C16 0.066(4) 0.057(5) 0.047(4) 0.012(4) 0.023(4) 0.016(4) C17 0.045(3) 0.039(4) 0.040(4) 0.019(4) -0.001(3) -0.004(3) C18 0.060(4) 0.030(4) 0.065(5) 0.000(4) 0.015(4) -0.002(3) C19 0.054(4) 0.044(4) 0.075(5) 0.019(4) 0.011(4) 0.009(3) C20 0.036(3) 0.040(4) 0.059(5) 0.001(4) 0.000(3) 0.001(3) C21 0.031(3) 0.032(4) 0.042(4) 0.009(3) -0.003(3) -0.007(3) C22 0.038(3) 0.047(4) 0.054(5) 0.008(4) 0.000(3) -0.002(3) C23 0.053(4) 0.038(5) 0.093(7) 0.011(4) 0.024(4) -0.002(3) C24 0.029(3) 0.047(5) 0.133(8) 0.028(5) -0.007(5) 0.000(3) C25 0.053(5) 0.057(5) 0.096(7) 0.031(5) -0.026(4) -0.016(3) C26 0.043(4) 0.055(4) 0.066(5) 0.007(4) -0.015(4) -0.007(3) _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 1.367(6) . ? O1 C20 1.463(6) . ? O2 C1 1.213(6) . ? O3 C4 1.312(6) . ? O3 C5 1.463(6) . ? O4 C4 1.194(6) . ? O5 C8 1.329(6) . ? O5 C9 1.452(6) . ? O6 C8 1.216(6) . ? N1 C1 1.340(6) . ? N1 C2 1.474(6) . ? N1 H1A 0.88(5) . ? C2 C13 1.511(7) . ? C2 C3 1.529(7) . ? C2 H2 1.0000 . ? C3 C7 1.509(7) . ? C3 C4 1.511(8) . ? C3 H3 1.0000 . ? C5 C6 1.483(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C11 1.531(7) . ? C7 C8 1.534(8) . ? C7 H7 1.0000 . ? C9 C10 1.494(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.495(7) . ? C11 C17 1.545(7) . ? C11 H11 1.0000 . ? C12 C13 1.350(7) . ? C12 H12 0.9500 . ? C13 C14 1.514(7) . ? C14 C15 1.514(7) . ? C14 C16 1.524(7) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.503(7) . ? C17 C19 1.539(7) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.508(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.364(8) . ? C21 C26 1.385(7) . ? C22 C23 1.399(8) . ? C22 H22 0.9500 . ? C23 C24 1.389(9) . ? C23 H23 0.9500 . ? C24 C25 1.369(10) . ? C24 H24 0.9500 . ? C25 C26 1.383(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C20 113.6(4) . . ? C4 O3 C5 115.8(5) . . ? C8 O5 C9 116.2(4) . . ? C1 N1 C2 121.6(5) . . ? C1 N1 H1A 116(3) . . ? C2 N1 H1A 121(3) . . ? O2 C1 N1 127.3(5) . . ? O2 C1 O1 123.6(5) . . ? N1 C1 O1 109.2(5) . . ? N1 C2 C13 109.7(4) . . ? N1 C2 C3 112.2(5) . . ? C13 C2 C3 113.0(4) . . ? N1 C2 H2 107.2 . . ? C13 C2 H2 107.2 . . ? C3 C2 H2 107.2 . . ? C7 C3 C4 112.6(5) . . ? C7 C3 C2 110.7(5) . . ? C4 C3 C2 110.1(4) . . ? C7 C3 H3 107.8 . . ? C4 C3 H3 107.8 . . ? C2 C3 H3 107.8 . . ? O4 C4 O3 123.9(6) . . ? O4 C4 C3 123.3(6) . . ? O3 C4 C3 112.7(5) . . ? O3 C5 C6 109.3(6) . . ? O3 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 C11 110.6(5) . . ? C3 C7 C8 111.0(5) . . ? C11 C7 C8 108.4(4) . . ? C3 C7 H7 108.9 . . ? C11 C7 H7 108.9 . . ? C8 C7 H7 108.9 . . ? O6 C8 O5 123.7(5) . . ? O6 C8 C7 124.6(5) . . ? O5 C8 C7 111.6(5) . . ? O5 C9 C10 105.9(4) . . ? O5 C9 H9A 110.6 . . ? C10 C9 H9A 110.6 . . ? O5 C9 H9B 110.6 . . ? C10 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C7 108.6(4) . . ? C12 C11 C17 112.4(5) . . ? C7 C11 C17 112.7(5) . . ? C12 C11 H11 107.6 . . ? C7 C11 H11 107.6 . . ? C17 C11 H11 107.6 . . ? C13 C12 C11 125.6(5) . . ? C13 C12 H12 117.2 . . ? C11 C12 H12 117.2 . . ? C12 C13 C2 121.0(5) . . ? C12 C13 C14 122.4(5) . . ? C2 C13 C14 116.5(5) . . ? C15 C14 C13 113.0(4) . . ? C15 C14 C16 109.8(5) . . ? C13 C14 C16 111.6(4) . . ? C15 C14 H14 107.4 . . ? C13 C14 H14 107.4 . . ? C16 C14 H14 107.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 110.1(5) . . ? C18 C17 C11 111.6(4) . . ? C19 C17 C11 112.4(5) . . ? C18 C17 H17 107.5 . . ? C19 C17 H17 107.5 . . ? C11 C17 H17 107.5 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 C21 106.6(4) . . ? O1 C20 H20A 110.4 . . ? C21 C20 H20A 110.4 . . ? O1 C20 H20B 110.4 . . ? C21 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? C22 C21 C26 120.0(5) . . ? C22 C21 C20 120.9(6) . . ? C26 C21 C20 119.1(6) . . ? C21 C22 C23 120.7(6) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 119.0(7) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C25 C24 C23 119.7(6) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 121.1(7) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 119.4(7) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? 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 C2 N1 C1 O2 -2.3(9) . . . . ? C2 N1 C1 O1 177.6(4) . . . . ? C20 O1 C1 O2 -2.0(8) . . . . ? C20 O1 C1 N1 178.2(5) . . . . ? C1 N1 C2 C13 -115.8(6) . . . . ? C1 N1 C2 C3 117.7(6) . . . . ? N1 C2 C3 C7 84.1(6) . . . . ? C13 C2 C3 C7 -40.6(6) . . . . ? N1 C2 C3 C4 -41.1(6) . . . . ? C13 C2 C3 C4 -165.8(4) . . . . ? C5 O3 C4 O4 -4.0(8) . . . . ? C5 O3 C4 C3 172.2(5) . . . . ? C7 C3 C4 O4 -3.3(8) . . . . ? C2 C3 C4 O4 120.7(6) . . . . ? C7 C3 C4 O3 -179.5(4) . . . . ? C2 C3 C4 O3 -55.5(6) . . . . ? C4 O3 C5 C6 -172.5(5) . . . . ? C4 C3 C7 C11 -172.1(4) . . . . ? C2 C3 C7 C11 64.2(6) . . . . ? C4 C3 C7 C8 -51.7(6) . . . . ? C2 C3 C7 C8 -175.4(4) . . . . ? C9 O5 C8 O6 6.6(8) . . . . ? C9 O5 C8 C7 -175.4(5) . . . . ? C3 C7 C8 O6 -55.9(7) . . . . ? C11 C7 C8 O6 65.7(7) . . . . ? C3 C7 C8 O5 126.1(5) . . . . ? C11 C7 C8 O5 -112.3(5) . . . . ? C8 O5 C9 C10 165.6(5) . . . . ? C3 C7 C11 C12 -51.5(6) . . . . ? C8 C7 C11 C12 -173.4(5) . . . . ? C3 C7 C11 C17 -176.7(4) . . . . ? C8 C7 C11 C17 61.4(6) . . . . ? C7 C11 C12 C13 19.2(7) . . . . ? C17 C11 C12 C13 144.6(5) . . . . ? C11 C12 C13 C2 2.5(8) . . . . ? C11 C12 C13 C14 -175.3(5) . . . . ? N1 C2 C13 C12 -117.9(5) . . . . ? C3 C2 C13 C12 8.2(7) . . . . ? N1 C2 C13 C14 60.1(6) . . . . ? C3 C2 C13 C14 -173.9(4) . . . . ? C12 C13 C14 C15 -61.4(7) . . . . ? C2 C13 C14 C15 120.7(5) . . . . ? C12 C13 C14 C16 62.9(6) . . . . ? C2 C13 C14 C16 -115.0(5) . . . . ? C12 C11 C17 C18 72.4(6) . . . . ? C7 C11 C17 C18 -164.4(5) . . . . ? C12 C11 C17 C19 -51.8(7) . . . . ? C7 C11 C17 C19 71.4(6) . . . . ? C1 O1 C20 C21 167.6(5) . . . . ? O1 C20 C21 C22 -107.5(6) . . . . ? O1 C20 C21 C26 73.5(7) . . . . ? C26 C21 C22 C23 0.8(9) . . . . ? C20 C21 C22 C23 -178.2(5) . . . . ? C21 C22 C23 C24 -0.8(9) . . . . ? C22 C23 C24 C25 -0.3(10) . . . . ? C23 C24 C25 C26 1.5(11) . . . . ? C24 C25 C26 C21 -1.5(10) . . . . ? C22 C21 C26 C25 0.4(9) . . . . ? C20 C21 C26 C25 179.4(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 # Attachment 'rob211.cif' data_rob211 _database_code_depnum_ccdc_archive 'CCDC 832708' #TrackingRef 'rob211.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H25 N O5' _chemical_formula_sum 'C18 H25 N O5' _chemical_formula_weight 335.39 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/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 8.3411(13) _cell_length_b 17.2794(17) _cell_length_c 12.2343(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.713(5) _cell_angle_gamma 90.00 _cell_volume 1743.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7318 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7318 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3532 _reflns_number_gt 1932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0510P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3532 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 0.62482(16) -0.04655(7) 0.17854(11) 0.0269(4) Uani 1 1 d . . . O2 O 0.68640(16) 0.01400(7) 0.34211(11) 0.0251(4) Uani 1 1 d . . . O3 O 0.37473(17) 0.07311(7) 0.21963(12) 0.0289(4) Uani 1 1 d . . . O4 O 1.01769(16) 0.00528(7) 0.28482(11) 0.0262(4) Uani 1 1 d . . . O5 O 1.03546(17) 0.10597(8) 0.40349(12) 0.0313(4) Uani 1 1 d . . . N1 N 0.4652(2) 0.08696(9) 0.05457(16) 0.0231(4) Uani 1 1 d . . . C1 C 0.6701(2) 0.01077(12) 0.23188(17) 0.0234(5) Uani 1 1 d . . . C2 C 0.6354(3) -0.05516(11) 0.39474(18) 0.0322(6) Uani 1 1 d . . . H2A H 0.5282 -0.0712 0.3574 0.048 Uiso 1 1 calc R . . H2B H 0.6298 -0.0442 0.4727 0.048 Uiso 1 1 calc R . . H2C H 0.7137 -0.0968 0.3897 0.048 Uiso 1 1 calc R . . C3 C 0.7207(2) 0.08478(11) 0.18351(17) 0.0211(5) Uani 1 1 d . . . C4 C 0.6199(2) 0.11927(10) 0.09536(17) 0.0221(5) Uani 1 1 d . . . C5 C 0.3529(3) 0.06539(10) 0.11833(19) 0.0249(5) Uani 1 1 d . . . C6 C 0.2014(2) 0.02993(11) 0.05679(18) 0.0312(6) Uani 1 1 d . . . H6A H 0.2074 -0.0265 0.0641 0.047 Uiso 1 1 calc R . . H6B H 0.1908 0.0441 -0.0215 0.047 Uiso 1 1 calc R . . H6C H 0.1071 0.0490 0.0876 0.047 Uiso 1 1 calc R . . C7 C 0.6727(2) 0.18565(11) 0.04404(17) 0.0221(5) Uani 1 1 d . . . C8 C 0.8267(3) 0.21415(11) 0.08435(18) 0.0241(5) Uani 1 1 d . . . C9 C 0.9294(2) 0.18209(11) 0.17270(17) 0.0232(5) Uani 1 1 d . . . C10 C 0.8725(2) 0.11658(11) 0.22307(16) 0.0229(5) Uani 1 1 d . . . C11 C 0.9824(2) 0.07724(11) 0.31550(18) 0.0246(5) Uani 1 1 d . . . C12 C 1.1336(3) -0.03665(12) 0.36304(19) 0.0335(6) Uani 1 1 d . . . H12A H 1.2363 -0.0081 0.3758 0.050 Uiso 1 1 calc R . . H12B H 1.1520 -0.0880 0.3332 0.050 Uiso 1 1 calc R . . H12C H 1.0911 -0.0423 0.4330 0.050 Uiso 1 1 calc R . . C13 C 1.0982(3) 0.21530(12) 0.21113(18) 0.0260(5) Uani 1 1 d . . . C14 C 1.0921(3) 0.28052(12) 0.29463(19) 0.0358(6) Uani 1 1 d . . . H14A H 1.0225 0.3223 0.2602 0.054 Uiso 1 1 calc R . . H14B H 1.2018 0.3005 0.3183 0.054 Uiso 1 1 calc R . . H14C H 1.0480 0.2607 0.3590 0.054 Uiso 1 1 calc R . . C15 C 1.1804(3) 0.24307(12) 0.11416(18) 0.0349(6) Uani 1 1 d . . . H15A H 1.1753 0.2020 0.0585 0.052 Uiso 1 1 calc R . . H15B H 1.2941 0.2557 0.1410 0.052 Uiso 1 1 calc R . . H15C H 1.1244 0.2892 0.0810 0.052 Uiso 1 1 calc R . . C16 C 0.5705(3) 0.22445(11) -0.05386(17) 0.0263(5) Uani 1 1 d . . . C17 C 0.6289(3) 0.20247(13) -0.16201(18) 0.0359(6) Uani 1 1 d . . . H17A H 0.7405 0.2206 -0.1607 0.054 Uiso 1 1 calc R . . H17B H 0.5585 0.2266 -0.2241 0.054 Uiso 1 1 calc R . . H17C H 0.6253 0.1461 -0.1707 0.054 Uiso 1 1 calc R . . C18 C 0.5671(3) 0.31260(12) -0.0420(2) 0.0436(6) Uani 1 1 d . . . H18A H 0.5363 0.3261 0.0298 0.065 Uiso 1 1 calc R . . H18B H 0.4880 0.3345 -0.1013 0.065 Uiso 1 1 calc R . . H18C H 0.6749 0.3337 -0.0468 0.065 Uiso 1 1 calc R . . H1 H 0.868(2) 0.2593(10) 0.0487(14) 0.016(5) Uiso 1 1 d . . . H2 H 0.457(3) 0.2049(10) -0.0553(16) 0.034(6) Uiso 1 1 d . . . H3 H 1.162(2) 0.1730(10) 0.2471(15) 0.019(5) Uiso 1 1 d . . . H4 H 0.443(3) 0.0777(11) -0.0162(19) 0.035(7) 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 0.0287(9) 0.0254(8) 0.0277(9) -0.0034(7) 0.0075(7) -0.0029(7) O2 0.0274(9) 0.0255(8) 0.0234(9) 0.0018(6) 0.0066(7) -0.0037(6) O3 0.0273(9) 0.0350(9) 0.0258(9) -0.0025(7) 0.0085(7) 0.0000(6) O4 0.0234(8) 0.0267(8) 0.0283(9) 0.0007(6) 0.0029(7) 0.0031(6) O5 0.0351(10) 0.0328(9) 0.0250(9) 0.0008(7) 0.0021(8) -0.0032(7) N1 0.0203(11) 0.0290(10) 0.0209(11) -0.0016(8) 0.0058(9) -0.0014(8) C1 0.0174(12) 0.0303(13) 0.0230(13) -0.0005(10) 0.0045(10) 0.0017(9) C2 0.0373(14) 0.0310(12) 0.0295(14) 0.0080(10) 0.0084(12) -0.0071(10) C3 0.0189(12) 0.0230(11) 0.0226(12) -0.0024(9) 0.0071(10) 0.0004(9) C4 0.0196(12) 0.0244(12) 0.0236(12) -0.0045(9) 0.0077(10) 0.0001(9) C5 0.0206(13) 0.0253(12) 0.0299(14) -0.0020(9) 0.0074(11) 0.0042(9) C6 0.0248(13) 0.0358(13) 0.0346(14) -0.0060(10) 0.0097(12) -0.0039(10) C7 0.0202(12) 0.0242(11) 0.0234(12) -0.0016(9) 0.0074(10) 0.0035(9) C8 0.0225(13) 0.0237(12) 0.0276(13) 0.0031(10) 0.0087(11) 0.0000(9) C9 0.0209(12) 0.0258(12) 0.0244(13) -0.0034(9) 0.0081(10) 0.0004(9) C10 0.0215(12) 0.0256(12) 0.0224(12) -0.0024(9) 0.0057(10) 0.0007(9) C11 0.0204(12) 0.0253(12) 0.0295(14) 0.0008(10) 0.0087(11) -0.0044(9) C12 0.0297(13) 0.0356(13) 0.0339(14) 0.0038(10) 0.0007(12) 0.0055(10) C13 0.0211(13) 0.0251(12) 0.0322(14) 0.0054(10) 0.0055(11) 0.0012(10) C14 0.0299(14) 0.0361(13) 0.0404(15) -0.0027(11) 0.0022(12) -0.0041(10) C15 0.0242(13) 0.0424(13) 0.0390(15) 0.0092(11) 0.0080(12) -0.0056(10) C16 0.0203(13) 0.0309(12) 0.0286(14) 0.0029(9) 0.0064(11) -0.0014(10) C17 0.0352(14) 0.0454(14) 0.0269(14) 0.0025(10) 0.0035(12) -0.0010(11) C18 0.0548(17) 0.0371(14) 0.0374(15) 0.0033(11) 0.0021(13) 0.0125(12) _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 1.214(2) . ? O2 C1 1.336(2) . ? O2 C2 1.451(2) . ? O3 C5 1.232(2) . ? O4 C11 1.344(2) . ? O4 C12 1.448(2) . ? O5 C11 1.207(2) . ? N1 C5 1.359(2) . ? N1 C4 1.425(3) . ? N1 H4 0.87(2) . ? C1 C3 1.496(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.396(3) . ? C3 C10 1.398(3) . ? C4 C7 1.410(3) . ? C5 C6 1.500(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.395(3) . ? C7 C16 1.517(3) . ? C8 C9 1.389(3) . ? C8 H1 0.979(17) . ? C9 C10 1.405(3) . ? C9 C13 1.527(3) . ? C10 C11 1.506(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.527(3) . ? C13 C15 1.535(3) . ? C13 H3 0.971(18) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.526(3) . ? C16 C18 1.531(3) . ? C16 H2 1.00(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 114.94(15) . . ? C11 O4 C12 115.52(16) . . ? C5 N1 C4 124.96(19) . . ? C5 N1 H4 117.4(14) . . ? C4 N1 H4 117.5(14) . . ? O1 C1 O2 123.52(17) . . ? O1 C1 C3 124.61(19) . . ? O2 C1 C3 111.83(17) . . ? O2 C2 H2A 109.5 . . ? O2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C10 120.48(17) . . ? C4 C3 C1 119.83(18) . . ? C10 C3 C1 119.60(19) . . ? C3 C4 C7 119.96(18) . . ? C3 C4 N1 120.69(17) . . ? C7 C4 N1 119.34(19) . . ? O3 C5 N1 122.5(2) . . ? O3 C5 C6 122.28(18) . . ? N1 C5 C6 115.18(19) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C4 117.57(19) . . ? C8 C7 C16 120.03(17) . . ? C4 C7 C16 122.37(18) . . ? C9 C8 C7 124.13(19) . . ? C9 C8 H1 116.7(11) . . ? C7 C8 H1 119.2(11) . . ? C8 C9 C10 116.94(19) . . ? C8 C9 C13 121.40(18) . . ? C10 C9 C13 121.65(19) . . ? C3 C10 C9 120.89(19) . . ? C3 C10 C11 119.94(17) . . ? C9 C10 C11 119.02(18) . . ? O5 C11 O4 124.3(2) . . ? O5 C11 C10 125.69(19) . . ? O4 C11 C10 110.00(18) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 111.14(16) . . ? C9 C13 C15 112.25(18) . . ? C14 C13 C15 110.52(17) . . ? C9 C13 H3 106.0(10) . . ? C14 C13 H3 109.0(11) . . ? C15 C13 H3 107.8(10) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 C16 C17 111.08(17) . . ? C7 C16 C18 112.39(18) . . ? C17 C16 C18 110.07(17) . . ? C7 C16 H2 106.3(11) . . ? C17 C16 H2 109.0(11) . . ? C18 C16 H2 107.8(11) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.261 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051 # Attachment 'rob284.cif' data_rob284 _database_code_depnum_ccdc_archive 'CCDC 832709' #TrackingRef 'rob284.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N O5' _chemical_formula_sum 'C26 H25 N O5' _chemical_formula_weight 431.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.6003(6) _cell_length_b 17.4066(8) _cell_length_c 9.8449(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.519(2) _cell_angle_gamma 90.00 _cell_volume 2257.91(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4577 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .07 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4577 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2478 _reflns_number_gt 2111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(9) _refine_ls_number_reflns 2478 _refine_ls_number_parameters 297 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.05322(11) 0.27469(10) 0.35441(15) 0.0330(4) Uani 1 1 d . . . O2 O 0.08240(12) 0.07328(9) 0.39921(17) 0.0309(4) Uani 1 1 d . . . O3 O 0.11154(12) 0.15532(10) 0.59013(16) 0.0316(4) Uani 1 1 d . . . O4 O 0.27705(11) 0.02981(9) 0.68559(15) 0.0262(3) Uani 1 1 d . . . O5 O 0.15226(13) 0.33569(10) 0.56906(19) 0.0387(4) Uani 1 1 d . . . N1 N 0.29215(13) 0.03535(10) 0.46722(19) 0.0206(4) Uani 1 1 d . . . H1 H 0.2888(18) 0.0097(15) 0.390(3) 0.030(6) Uiso 1 1 d . . . C1 C 0.22559(16) 0.24225(13) 0.4660(2) 0.0247(5) Uani 1 1 d . . . C2 C 0.22117(16) 0.16220(13) 0.4735(2) 0.0208(4) Uani 1 1 d . . . C3 C 0.13126(16) 0.12400(13) 0.4810(2) 0.0239(5) Uani 1 1 d . . . C4 C 0.0286(2) 0.12112(19) 0.6118(3) 0.0477(7) Uani 1 1 d . . . H4A H -0.0333 0.1231 0.5172 0.072 Uiso 1 1 calc R . . H4B H 0.0179 0.1496 0.6897 0.072 Uiso 1 1 calc R . . H4C H 0.0450 0.0675 0.6432 0.072 Uiso 1 1 calc R . . C5 C 0.29857(16) 0.11710(12) 0.4662(2) 0.0207(4) Uani 1 1 d . . . C6 C 0.27172(15) -0.00259(13) 0.5704(2) 0.0219(4) Uani 1 1 d . . . C7 C 0.23919(15) -0.08467(13) 0.5404(2) 0.0235(5) Uani 1 1 d . . . C8 C 0.26760(16) -0.13318(13) 0.4528(2) 0.0256(5) Uani 1 1 d . . . H8 H 0.3069 -0.1138 0.4046 0.031 Uiso 1 1 calc R . . C9 C 0.23867(18) -0.20976(14) 0.4358(2) 0.0322(5) Uani 1 1 d . . . H9 H 0.2589 -0.2428 0.3769 0.039 Uiso 1 1 calc R . . C10 C 0.18068(18) -0.23815(14) 0.5038(2) 0.0336(6) Uani 1 1 d . . . H10 H 0.1627 -0.2910 0.4940 0.040 Uiso 1 1 calc R . . C11 C 0.14843(18) -0.18989(15) 0.5866(2) 0.0314(5) Uani 1 1 d . . . H11 H 0.1066 -0.2092 0.6307 0.038 Uiso 1 1 calc R . . C12 C 0.17754(17) -0.11337(13) 0.6047(2) 0.0261(5) Uani 1 1 d . . . H12 H 0.1554 -0.0802 0.6613 0.031 Uiso 1 1 calc R . . C13 C 0.37797(16) 0.15261(12) 0.4464(2) 0.0205(4) Uani 1 1 d . . . C14 C 0.37774(17) 0.23262(13) 0.4356(2) 0.0235(5) Uani 1 1 d . . . H14 H 0.4311 0.2565 0.4206 0.028 Uiso 1 1 calc R . . C15 C 0.30370(16) 0.27898(13) 0.4457(2) 0.0239(5) Uani 1 1 d . . . C16 C 0.30887(18) 0.36615(13) 0.4353(2) 0.0298(5) Uani 1 1 d . . . H16 H 0.2379 0.3863 0.3963 0.036 Uiso 1 1 calc R . . C17 C 0.3531(2) 0.39335(15) 0.3281(3) 0.0396(6) Uani 1 1 d . . . H17A H 0.4257 0.3810 0.3711 0.059 Uiso 1 1 calc R . . H17B H 0.3440 0.4490 0.3138 0.059 Uiso 1 1 calc R . . H17C H 0.3181 0.3674 0.2309 0.059 Uiso 1 1 calc R . . C18 C 0.3695(2) 0.40061(15) 0.5925(3) 0.0414(6) Uani 1 1 d . . . H18A H 0.3367 0.3871 0.6576 0.062 Uiso 1 1 calc R . . H18B H 0.3717 0.4566 0.5847 0.062 Uiso 1 1 calc R . . H18C H 0.4387 0.3801 0.6357 0.062 Uiso 1 1 calc R . . C19 C 0.46180(15) 0.10992(12) 0.4329(2) 0.0215(5) Uani 1 1 d . . . C20 C 0.48412(16) 0.12549(13) 0.3116(2) 0.0240(5) Uani 1 1 d . . . H20 H 0.4424 0.1601 0.2354 0.029 Uiso 1 1 calc R . . C21 C 0.56637(17) 0.09128(14) 0.3006(2) 0.0283(5) Uani 1 1 d . . . H21 H 0.5803 0.1020 0.2168 0.034 Uiso 1 1 calc R . . C22 C 0.62794(17) 0.04167(14) 0.4119(2) 0.0289(5) Uani 1 1 d . . . H22 H 0.6853 0.0190 0.4058 0.035 Uiso 1 1 calc R . . C23 C 0.60609(17) 0.02502(14) 0.5321(2) 0.0299(5) Uani 1 1 d . . . H23 H 0.6480 -0.0097 0.6078 0.036 Uiso 1 1 calc R . . C24 C 0.52351(17) 0.05873(13) 0.5429(2) 0.0264(5) Uani 1 1 d . . . H24 H 0.5089 0.0469 0.6257 0.032 Uiso 1 1 calc R . . C25 C 0.14165(17) 0.28965(14) 0.4724(2) 0.0272(5) Uani 1 1 d . . . C26 C -0.03361(19) 0.31449(17) 0.3557(3) 0.0415(7) Uani 1 1 d . . . H25A H -0.0401 0.3016 0.4481 0.062 Uiso 1 1 calc R . . H25B H -0.0953 0.2987 0.2681 0.062 Uiso 1 1 calc R . . H25C H -0.0242 0.3701 0.3518 0.062 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 0.0276(9) 0.0435(11) 0.0276(8) 0.0017(7) 0.0117(7) 0.0104(7) O2 0.0259(8) 0.0350(10) 0.0306(8) -0.0007(8) 0.0110(6) -0.0019(7) O3 0.0314(9) 0.0412(10) 0.0302(8) 0.0009(7) 0.0208(7) 0.0035(7) O4 0.0367(9) 0.0238(9) 0.0223(7) 0.0001(6) 0.0169(7) 0.0010(7) O5 0.0432(10) 0.0353(10) 0.0438(10) -0.0096(9) 0.0245(8) 0.0052(8) N1 0.0260(9) 0.0196(10) 0.0186(8) -0.0015(8) 0.0118(7) 0.0006(8) C1 0.0260(11) 0.0283(13) 0.0191(10) -0.0015(9) 0.0090(9) 0.0041(10) C2 0.0239(11) 0.0249(12) 0.0152(9) -0.0009(9) 0.0098(8) 0.0008(9) C3 0.0237(11) 0.0265(13) 0.0221(10) 0.0053(10) 0.0105(9) 0.0059(10) C4 0.0375(15) 0.069(2) 0.0501(15) 0.0006(14) 0.0312(13) -0.0023(14) C5 0.0258(11) 0.0216(11) 0.0149(9) -0.0004(9) 0.0089(8) 0.0006(10) C6 0.0198(11) 0.0250(12) 0.0205(10) 0.0003(9) 0.0082(8) 0.0026(9) C7 0.0229(11) 0.0267(13) 0.0173(10) 0.0017(9) 0.0052(9) 0.0003(9) C8 0.0301(12) 0.0255(13) 0.0216(11) -0.0002(9) 0.0115(9) -0.0009(10) C9 0.0386(14) 0.0268(14) 0.0282(12) -0.0038(10) 0.0116(10) 0.0008(11) C10 0.0361(14) 0.0278(14) 0.0288(12) 0.0002(10) 0.0065(10) -0.0099(11) C11 0.0287(12) 0.0365(15) 0.0267(12) 0.0014(10) 0.0098(10) -0.0100(11) C12 0.0275(12) 0.0289(13) 0.0210(10) 0.0001(9) 0.0098(9) -0.0008(9) C13 0.0235(11) 0.0202(12) 0.0179(9) 0.0005(8) 0.0089(8) 0.0013(9) C14 0.0229(11) 0.0259(12) 0.0229(10) 0.0006(9) 0.0111(9) -0.0003(10) C15 0.0242(11) 0.0242(12) 0.0202(10) -0.0033(9) 0.0066(9) 0.0007(10) C16 0.0297(12) 0.0209(12) 0.0355(12) -0.0005(10) 0.0107(10) 0.0035(10) C17 0.0447(16) 0.0268(14) 0.0480(14) 0.0077(11) 0.0206(12) 0.0017(11) C18 0.0438(15) 0.0272(14) 0.0472(14) -0.0097(11) 0.0139(12) -0.0028(11) C19 0.0209(11) 0.0208(12) 0.0232(10) -0.0033(9) 0.0099(9) -0.0014(9) C20 0.0257(11) 0.0204(12) 0.0244(10) -0.0019(9) 0.0095(9) -0.0042(9) C21 0.0349(13) 0.0263(13) 0.0298(12) -0.0041(9) 0.0197(10) -0.0037(10) C22 0.0301(12) 0.0231(12) 0.0393(12) -0.0046(10) 0.0203(10) 0.0009(10) C23 0.0322(13) 0.0245(14) 0.0345(12) 0.0037(10) 0.0157(10) 0.0054(10) C24 0.0314(12) 0.0243(13) 0.0275(11) 0.0033(9) 0.0165(10) 0.0014(10) C25 0.0320(13) 0.0273(13) 0.0265(11) 0.0035(10) 0.0166(10) 0.0045(10) C26 0.0313(14) 0.0544(19) 0.0427(14) 0.0072(13) 0.0196(12) 0.0171(12) _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 C25 1.339(3) . ? O1 C26 1.450(3) . ? O2 C3 1.201(3) . ? O3 C3 1.342(2) . ? O3 C4 1.445(3) . ? O4 C6 1.238(2) . ? O5 C25 1.202(3) . ? N1 C6 1.349(3) . ? N1 C5 1.426(3) . ? N1 H1 0.87(2) . ? C1 C15 1.395(3) . ? C1 C2 1.398(3) . ? C1 C25 1.501(3) . ? C2 C5 1.403(3) . ? C2 C3 1.501(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C13 1.400(3) . ? C6 C7 1.495(3) . ? C7 C8 1.392(3) . ? C7 C12 1.397(3) . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.397(3) . ? C13 C19 1.486(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.525(3) . ? C16 C17 1.530(3) . ? C16 C18 1.536(3) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.392(3) . ? C19 C20 1.393(3) . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 C23 1.383(3) . ? C22 H22 0.9500 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C26 H25A 0.9800 . ? C26 H25B 0.9800 . ? C26 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 C26 114.79(18) . . ? C3 O3 C4 115.67(19) . . ? C6 N1 C5 122.02(17) . . ? C6 N1 H1 117.7(16) . . ? C5 N1 H1 119.1(16) . . ? C15 C1 C2 121.56(18) . . ? C15 C1 C25 119.1(2) . . ? C2 C1 C25 119.24(19) . . ? C1 C2 C5 119.90(18) . . ? C1 C2 C3 120.33(18) . . ? C5 C2 C3 119.69(19) . . ? O2 C3 O3 124.42(19) . . ? O2 C3 C2 124.89(18) . . ? O3 C3 C2 110.68(18) . . ? O3 C4 H4A 109.5 . . ? O3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C13 C5 C2 119.59(18) . . ? C13 C5 N1 120.15(18) . . ? C2 C5 N1 120.08(19) . . ? O4 C6 N1 121.3(2) . . ? O4 C6 C7 120.38(18) . . ? N1 C6 C7 118.28(17) . . ? C8 C7 C12 119.1(2) . . ? C8 C7 C6 123.26(19) . . ? C12 C7 C6 117.65(18) . . ? C9 C8 C7 120.11(19) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 120.5(2) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C14 C13 C5 118.41(18) . . ? C14 C13 C19 117.85(18) . . ? C5 C13 C19 123.72(18) . . ? C15 C14 C13 123.5(2) . . ? C15 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? C14 C15 C1 117.0(2) . . ? C14 C15 C16 120.76(19) . . ? C1 C15 C16 122.22(18) . . ? C15 C16 C17 113.73(18) . . ? C15 C16 C18 110.13(18) . . ? C17 C16 C18 110.0(2) . . ? C15 C16 H16 107.6 . . ? C17 C16 H16 107.6 . . ? C18 C16 H16 107.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 118.63(19) . . ? C24 C19 C13 122.21(18) . . ? C20 C19 C13 119.00(19) . . ? C21 C20 C19 120.9(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 119.79(19) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 120.3(2) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? O5 C25 O1 124.3(2) . . ? O5 C25 C1 124.8(2) . . ? O1 C25 C1 110.87(19) . . ? O1 C26 H25A 109.5 . . ? O1 C26 H25B 109.5 . . ? H25A C26 H25B 109.5 . . ? O1 C26 H25C 109.5 . . ? H25A C26 H25C 109.5 . . ? H25B C26 H25C 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 C15 C1 C2 C5 2.4(3) . . . . ? C25 C1 C2 C5 179.40(18) . . . . ? C15 C1 C2 C3 -174.32(18) . . . . ? C25 C1 C2 C3 2.7(3) . . . . ? C4 O3 C3 O2 3.4(3) . . . . ? C4 O3 C3 C2 -177.75(19) . . . . ? C1 C2 C3 O2 128.0(2) . . . . ? C5 C2 C3 O2 -48.7(3) . . . . ? C1 C2 C3 O3 -50.8(2) . . . . ? C5 C2 C3 O3 132.46(19) . . . . ? C1 C2 C5 C13 -2.2(3) . . . . ? C3 C2 C5 C13 174.60(17) . . . . ? C1 C2 C5 N1 -177.28(17) . . . . ? C3 C2 C5 N1 -0.5(3) . . . . ? C6 N1 C5 C13 135.22(19) . . . . ? C6 N1 C5 C2 -49.7(3) . . . . ? C5 N1 C6 O4 -14.3(3) . . . . ? C5 N1 C6 C7 163.91(19) . . . . ? O4 C6 C7 C8 -154.0(2) . . . . ? N1 C6 C7 C8 27.8(3) . . . . ? O4 C6 C7 C12 25.8(3) . . . . ? N1 C6 C7 C12 -152.44(18) . . . . ? C12 C7 C8 C9 -2.9(3) . . . . ? C6 C7 C8 C9 176.84(19) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? C8 C9 C10 C11 1.8(3) . . . . ? C9 C10 C11 C12 -2.1(3) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C8 C7 C12 C11 2.6(3) . . . . ? C6 C7 C12 C11 -177.18(19) . . . . ? C2 C5 C13 C14 0.5(3) . . . . ? N1 C5 C13 C14 175.64(18) . . . . ? C2 C5 C13 C19 -178.21(18) . . . . ? N1 C5 C13 C19 -3.1(3) . . . . ? C5 C13 C14 C15 0.9(3) . . . . ? C19 C13 C14 C15 179.76(18) . . . . ? C13 C14 C15 C1 -0.7(3) . . . . ? C13 C14 C15 C16 179.13(19) . . . . ? C2 C1 C15 C14 -1.0(3) . . . . ? C25 C1 C15 C14 -177.96(18) . . . . ? C2 C1 C15 C16 179.17(18) . . . . ? C25 C1 C15 C16 2.2(3) . . . . ? C14 C15 C16 C17 34.4(3) . . . . ? C1 C15 C16 C17 -145.7(2) . . . . ? C14 C15 C16 C18 -89.6(2) . . . . ? C1 C15 C16 C18 90.2(2) . . . . ? C14 C13 C19 C24 124.9(2) . . . . ? C5 C13 C19 C24 -56.4(3) . . . . ? C14 C13 C19 C20 -50.5(3) . . . . ? C5 C13 C19 C20 128.2(2) . . . . ? C24 C19 C20 C21 -0.4(3) . . . . ? C13 C19 C20 C21 175.15(19) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? C20 C21 C22 C23 1.4(3) . . . . ? C21 C22 C23 C24 -1.0(3) . . . . ? C22 C23 C24 C19 -0.2(3) . . . . ? C20 C19 C24 C23 0.9(3) . . . . ? C13 C19 C24 C23 -174.6(2) . . . . ? C26 O1 C25 O5 -4.6(3) . . . . ? C26 O1 C25 C1 176.45(19) . . . . ? C15 C1 C25 O5 -64.9(3) . . . . ? C2 C1 C25 O5 118.1(3) . . . . ? C15 C1 C25 O1 114.1(2) . . . . ? C2 C1 C25 O1 -62.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.176 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.035 # Attachment 'rob290.cif' data_rob290 _database_code_depnum_ccdc_archive 'CCDC 832710' #TrackingRef 'rob290.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N2 O3' _chemical_formula_sum 'C12 H16 N2 O3' _chemical_formula_weight 236.27 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 Pbca 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' '-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 10.9806(6) _cell_length_b 8.1088(4) _cell_length_c 26.2218(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2334.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12480 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 27.00 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12480 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2549 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0677P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2549 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.26318(12) 0.11664(15) 0.13571(6) 0.0294(4) Uani 1 1 d . . . O2 O 0.01635(13) -0.23344(18) 0.22375(6) 0.0355(4) Uani 1 1 d . . . O3 O -0.01271(12) 0.27600(16) -0.01410(5) 0.0282(4) Uani 1 1 d . . . N1 N 0.15634(14) -0.05540(19) 0.18895(6) 0.0246(4) Uani 1 1 d . . . H1 H 0.192(2) 0.209(2) 0.0653(8) 0.030(6) Uiso 1 1 d . . . N2 N 0.11534(15) 0.20211(19) 0.04961(7) 0.0237(4) Uani 1 1 d . . . C1 C 0.18060(17) 0.0177(2) 0.14293(8) 0.0234(5) Uani 1 1 d . . . C2 C 0.05418(18) -0.1574(2) 0.18731(9) 0.0261(5) Uani 1 1 d . . . C3 C 0.00111(16) -0.1515(2) 0.13424(8) 0.0230(5) Uani 1 1 d . . . H3 H -0.0015 -0.2650 0.1194 0.028 Uiso 1 1 calc R . . C4 C 0.08965(16) -0.0434(2) 0.10380(8) 0.0213(5) Uani 1 1 d . . . H4 H 0.1325 -0.1123 0.0778 0.026 Uiso 1 1 calc R . . C5 C 0.02609(16) 0.1038(2) 0.07721(8) 0.0219(5) Uani 1 1 d . . . H5 H -0.0325 0.0579 0.0517 0.026 Uiso 1 1 calc R . . C6 C 0.08888(18) 0.2823(2) 0.00581(8) 0.0228(5) Uani 1 1 d . . . C7 C 0.19163(18) 0.3817(2) -0.01690(8) 0.0273(5) Uani 1 1 d . . . H7A H 0.1903 0.3708 -0.0541 0.041 Uiso 1 1 calc R . . H7B H 0.2695 0.3408 -0.0038 0.041 Uiso 1 1 calc R . . H7C H 0.1818 0.4980 -0.0076 0.041 Uiso 1 1 calc R . . C8 C -0.04735(16) 0.1967(2) 0.11732(8) 0.0225(5) Uani 1 1 d . . . C9 C -0.12228(17) 0.1050(2) 0.14520(8) 0.0255(5) Uani 1 1 d . . . H9 H -0.1717 0.1548 0.1707 0.031 Uiso 1 1 calc R . . C10 C -0.12861(16) -0.0781(2) 0.13629(8) 0.0270(5) Uani 1 1 d . . . H10A H -0.1713 -0.1005 0.1038 0.032 Uiso 1 1 calc R . . H10B H -0.1753 -0.1310 0.1642 0.032 Uiso 1 1 calc R . . C11 C -0.02764(19) 0.3782(2) 0.12472(9) 0.0297(5) Uani 1 1 d . . . H11A H -0.0862 0.4203 0.1498 0.045 Uiso 1 1 calc R . . H11B H -0.0393 0.4355 0.0922 0.045 Uiso 1 1 calc R . . H11C H 0.0554 0.3975 0.1371 0.045 Uiso 1 1 calc R . . C12 C 0.2272(2) -0.0283(4) 0.23508(10) 0.0372(6) Uani 1 1 d . . . H12A H 0.296(2) 0.042(3) 0.2281(10) 0.057(8) Uiso 1 1 d . . . H12B H 0.260(3) -0.129(4) 0.2454(12) 0.079(10) Uiso 1 1 d . . . H12C H 0.177(3) 0.024(4) 0.2639(12) 0.075(9) 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 0.0217(7) 0.0292(8) 0.0373(10) 0.0052(7) -0.0049(7) -0.0051(6) O2 0.0368(9) 0.0363(8) 0.0332(10) 0.0092(8) 0.0043(7) -0.0031(7) O3 0.0237(8) 0.0305(8) 0.0303(9) 0.0020(7) -0.0060(7) -0.0023(6) N1 0.0262(9) 0.0227(8) 0.0249(11) 0.0020(8) -0.0031(8) -0.0006(7) N2 0.0170(9) 0.0261(9) 0.0282(10) 0.0030(8) -0.0022(8) -0.0026(7) C1 0.0187(9) 0.0206(10) 0.0310(13) 0.0008(10) 0.0002(9) 0.0041(8) C2 0.0271(11) 0.0199(10) 0.0314(13) 0.0008(10) 0.0042(10) 0.0034(9) C3 0.0215(10) 0.0193(9) 0.0282(13) 0.0010(9) 0.0011(9) -0.0013(8) C4 0.0175(9) 0.0209(9) 0.0255(11) -0.0020(9) 0.0006(8) 0.0012(8) C5 0.0166(9) 0.0225(10) 0.0266(12) 0.0012(9) -0.0015(9) -0.0014(8) C6 0.0225(10) 0.0206(10) 0.0252(12) -0.0034(9) -0.0003(9) 0.0018(8) C7 0.0243(11) 0.0303(12) 0.0274(13) 0.0026(9) 0.0001(9) -0.0011(9) C8 0.0165(9) 0.0236(10) 0.0272(12) 0.0014(9) -0.0033(9) 0.0016(8) C9 0.0186(10) 0.0271(11) 0.0309(13) -0.0026(9) 0.0009(9) 0.0048(8) C10 0.0174(10) 0.0292(11) 0.0343(13) 0.0016(10) 0.0024(9) -0.0033(8) C11 0.0272(11) 0.0239(11) 0.0380(14) 0.0000(10) 0.0005(10) 0.0029(9) C12 0.0412(15) 0.0388(15) 0.0317(15) 0.0039(12) -0.0113(12) -0.0040(13) _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 1.225(2) . ? O2 C2 1.211(2) . ? O3 C6 1.233(2) . ? N1 C1 1.371(3) . ? N1 C2 1.394(3) . ? N1 C12 1.455(3) . ? N2 C6 1.351(3) . ? N2 C5 1.456(2) . ? N2 H1 0.93(2) . ? C1 C4 1.515(3) . ? C2 C3 1.509(3) . ? C3 C4 1.533(3) . ? C3 C10 1.545(3) . ? C3 H3 1.0000 . ? C4 C5 1.548(2) . ? C4 H4 1.0000 . ? C5 C8 1.524(3) . ? C5 H5 1.0000 . ? C6 C7 1.509(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.328(3) . ? C8 C11 1.501(3) . ? C9 C10 1.505(3) . ? C9 H9 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.96(3) . ? C12 H12B 0.93(3) . ? C12 H12C 1.03(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 112.69(17) . . ? C1 N1 C12 124.25(18) . . ? C2 N1 C12 123.04(19) . . ? C6 N2 C5 122.76(17) . . ? C6 N2 H1 122.4(12) . . ? C5 N2 H1 114.8(12) . . ? O1 C1 N1 124.27(19) . . ? O1 C1 C4 126.68(19) . . ? N1 C1 C4 109.05(16) . . ? O2 C2 N1 123.6(2) . . ? O2 C2 C3 127.68(18) . . ? N1 C2 C3 108.68(17) . . ? C2 C3 C4 104.67(15) . . ? C2 C3 C10 109.65(16) . . ? C4 C3 C10 112.51(15) . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? C10 C3 H3 110.0 . . ? C1 C4 C3 104.63(16) . . ? C1 C4 C5 110.47(15) . . ? C3 C4 C5 112.90(14) . . ? C1 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? N2 C5 C8 115.36(15) . . ? N2 C5 C4 110.03(14) . . ? C8 C5 C4 107.98(15) . . ? N2 C5 H5 107.7 . . ? C8 C5 H5 107.7 . . ? C4 C5 H5 107.7 . . ? O3 C6 N2 122.32(18) . . ? O3 C6 C7 122.11(18) . . ? N2 C6 C7 115.56(18) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C11 124.57(18) . . ? C9 C8 C5 115.51(16) . . ? C11 C8 C5 119.85(17) . . ? C8 C9 C10 119.70(18) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C3 110.05(15) . . ? C9 C10 H10A 109.6 . . ? C3 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C3 C10 H10B 109.6 . . ? H10A C10 H10B 108.2 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 110.4(15) . . ? N1 C12 H12B 108.3(19) . . ? H12A C12 H12B 106(2) . . ? N1 C12 H12C 112.7(16) . . ? H12A C12 H12C 108(2) . . ? H12B C12 H12C 111(3) . . ? 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 C2 N1 C1 O1 177.36(17) . . . . ? C12 N1 C1 O1 -1.5(3) . . . . ? C2 N1 C1 C4 -2.5(2) . . . . ? C12 N1 C1 C4 178.60(19) . . . . ? C1 N1 C2 O2 -179.72(18) . . . . ? C12 N1 C2 O2 -0.8(3) . . . . ? C1 N1 C2 C3 -1.0(2) . . . . ? C12 N1 C2 C3 177.91(19) . . . . ? O2 C2 C3 C4 -177.39(19) . . . . ? N1 C2 C3 C4 3.93(19) . . . . ? O2 C2 C3 C10 61.7(3) . . . . ? N1 C2 C3 C10 -116.97(16) . . . . ? O1 C1 C4 C3 -175.05(17) . . . . ? N1 C1 C4 C3 4.83(19) . . . . ? O1 C1 C4 C5 -53.3(2) . . . . ? N1 C1 C4 C5 126.61(16) . . . . ? C2 C3 C4 C1 -5.13(18) . . . . ? C10 C3 C4 C1 113.86(17) . . . . ? C2 C3 C4 C5 -125.31(16) . . . . ? C10 C3 C4 C5 -6.3(2) . . . . ? C6 N2 C5 C8 -90.2(2) . . . . ? C6 N2 C5 C4 147.32(17) . . . . ? C1 C4 C5 N2 62.5(2) . . . . ? C3 C4 C5 N2 179.29(16) . . . . ? C1 C4 C5 C8 -64.18(18) . . . . ? C3 C4 C5 C8 52.6(2) . . . . ? C5 N2 C6 O3 -0.8(3) . . . . ? C5 N2 C6 C7 178.54(16) . . . . ? N2 C5 C8 C9 -175.14(17) . . . . ? C4 C5 C8 C9 -51.6(2) . . . . ? N2 C5 C8 C11 2.0(3) . . . . ? C4 C5 C8 C11 125.52(18) . . . . ? C11 C8 C9 C10 -176.22(19) . . . . ? C5 C8 C9 C10 0.8(3) . . . . ? C8 C9 C10 C3 48.1(3) . . . . ? C2 C3 C10 C9 73.9(2) . . . . ? C4 C3 C10 C9 -42.1(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.190 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.049 # Attachment 'rob387.cif' data_rob387 _database_code_depnum_ccdc_archive 'CCDC 832711' #TrackingRef 'rob387.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 N2 O3' _chemical_formula_sum 'C17 H24 N2 O3' _chemical_formula_weight 304.38 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 7.9089(7) _cell_length_b 9.6396(9) _cell_length_c 10.547(8) _cell_angle_alpha 90.566(5) _cell_angle_beta 97.780(5) _cell_angle_gamma 97.777(4) _cell_volume 789.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4616 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4616 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3433 _reflns_number_gt 2229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0559P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3433 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 -0.03236(18) 0.14126(13) 0.17682(11) 0.0297(3) Uani 1 1 d . . . O2 O 0.22874(18) 0.50050(13) -0.03370(12) 0.0295(4) Uani 1 1 d . . . O3 O 0.05613(18) 0.33802(13) 0.63837(12) 0.0298(4) Uani 1 1 d . . . N1 N 0.1082(2) 0.29942(15) 0.05189(13) 0.0228(4) Uani 1 1 d . . . N2 N 0.0180(2) 0.24352(16) 0.43898(15) 0.0237(4) Uani 1 1 d . . . C1 C 0.0365(2) 0.2597(2) 0.16048(17) 0.0228(4) Uani 1 1 d . . . C2 C 0.1772(2) 0.44030(19) 0.05752(17) 0.0230(4) Uani 1 1 d . . . C3 C 0.1738(2) 0.50006(18) 0.18965(16) 0.0206(4) Uani 1 1 d . . . H3 H 0.1174 0.5869 0.1813 0.025 Uiso 1 1 calc R . . C4 C 0.0555(2) 0.38669(18) 0.24950(16) 0.0215(4) Uani 1 1 d . . . H4 H -0.0598 0.4182 0.2501 0.026 Uiso 1 1 calc R . . C5 C 0.1295(2) 0.35454(18) 0.38736(16) 0.0219(4) Uani 1 1 d . . . H5 H 0.1362 0.4410 0.4420 0.026 Uiso 1 1 calc R . . C6 C -0.0093(2) 0.24245(19) 0.56197(17) 0.0224(4) Uani 1 1 d . . . C7 C -0.1256(3) 0.11862(19) 0.60146(18) 0.0287(5) Uani 1 1 d . . . H7A H -0.0628 0.0710 0.6707 0.043 Uiso 1 1 calc R . . H7B H -0.1637 0.0535 0.5281 0.043 Uiso 1 1 calc R . . H7C H -0.2262 0.1506 0.6314 0.043 Uiso 1 1 calc R . . C8 C 0.3099(2) 0.32179(19) 0.38520(17) 0.0231(4) Uani 1 1 d . . . H8 H 0.3451 0.2413 0.4267 0.028 Uiso 1 1 calc R . . C9 C 0.4204(2) 0.40481(19) 0.32558(17) 0.0225(4) Uani 1 1 d . . . C10 C 0.3555(3) 0.53686(19) 0.26895(18) 0.0268(5) Uani 1 1 d . . . H10 H 0.3381 0.5948 0.3441 0.032 Uiso 1 1 calc R . . C11 C 0.4847(3) 0.6295(2) 0.19979(19) 0.0310(5) Uani 1 1 d . . . H11A H 0.5933 0.6540 0.2589 0.037 Uiso 1 1 calc R . . H11B H 0.5108 0.5757 0.1261 0.037 Uiso 1 1 calc R . . C12 C 0.4203(3) 0.76224(19) 0.15245(19) 0.0274(5) Uani 1 1 d . . . H12 H 0.3310 0.7513 0.0817 0.033 Uiso 1 1 calc R . . C13 C 0.4723(3) 0.89302(19) 0.19674(18) 0.0255(5) Uani 1 1 d . . . C14 C 0.3934(3) 1.0141(2) 0.13559(19) 0.0341(5) Uani 1 1 d . . . H14A H 0.3104 0.9798 0.0607 0.051 Uiso 1 1 calc R . . H14B H 0.4842 1.0825 0.1089 0.051 Uiso 1 1 calc R . . H14C H 0.3343 1.0587 0.1975 0.051 Uiso 1 1 calc R . . C15 C 0.6097(3) 0.9338(2) 0.30773(19) 0.0361(5) Uani 1 1 d . . . H15A H 0.6590 0.8505 0.3389 0.054 Uiso 1 1 calc R . . H15B H 0.5598 0.9757 0.3765 0.054 Uiso 1 1 calc R . . H15C H 0.7004 1.0019 0.2804 0.054 Uiso 1 1 calc R . . C16 C 0.5996(3) 0.3763(2) 0.31671(18) 0.0298(5) Uani 1 1 d . . . H16A H 0.6187 0.2886 0.3592 0.045 Uiso 1 1 calc R . . H16B H 0.6824 0.4534 0.3587 0.045 Uiso 1 1 calc R . . H16C H 0.6153 0.3680 0.2265 0.045 Uiso 1 1 calc R . . C17 C 0.1032(3) 0.2082(2) -0.05989(17) 0.0307(5) Uani 1 1 d . . . H17A H 0.0789 0.2607 -0.1378 0.046 Uiso 1 1 calc R . . H17B H 0.0125 0.1284 -0.0585 0.046 Uiso 1 1 calc R . . H17C H 0.2147 0.1742 -0.0585 0.046 Uiso 1 1 calc R . . H1X H -0.031(2) 0.1775(19) 0.3848(17) 0.024(5) 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 0.0364(9) 0.0248(8) 0.0263(7) 0.0010(6) 0.0065(6) -0.0040(6) O2 0.0362(9) 0.0298(8) 0.0240(7) 0.0056(6) 0.0102(6) 0.0032(6) O3 0.0401(9) 0.0269(8) 0.0221(7) -0.0013(6) 0.0076(6) 0.0008(7) N1 0.0283(10) 0.0218(8) 0.0191(8) 0.0010(6) 0.0072(7) 0.0027(7) N2 0.0290(10) 0.0218(9) 0.0197(8) -0.0032(7) 0.0070(7) -0.0020(8) C1 0.0212(11) 0.0248(11) 0.0223(10) 0.0027(8) 0.0015(8) 0.0036(9) C2 0.0202(11) 0.0245(10) 0.0254(10) 0.0035(8) 0.0035(8) 0.0064(8) C3 0.0208(11) 0.0200(10) 0.0213(10) 0.0031(8) 0.0033(8) 0.0031(8) C4 0.0216(11) 0.0215(10) 0.0220(10) 0.0012(8) 0.0058(8) 0.0026(8) C5 0.0249(11) 0.0216(10) 0.0194(10) 0.0008(8) 0.0055(8) 0.0014(8) C6 0.0231(11) 0.0250(10) 0.0208(10) 0.0013(8) 0.0057(8) 0.0069(9) C7 0.0327(13) 0.0287(11) 0.0260(11) 0.0023(8) 0.0110(9) 0.0023(9) C8 0.0253(11) 0.0235(10) 0.0211(10) 0.0025(8) 0.0028(8) 0.0058(8) C9 0.0229(11) 0.0234(10) 0.0208(10) -0.0018(7) 0.0025(8) 0.0021(8) C10 0.0268(12) 0.0261(11) 0.0272(10) 0.0037(8) 0.0032(9) 0.0025(9) C11 0.0259(12) 0.0291(11) 0.0385(12) 0.0038(9) 0.0062(9) 0.0039(9) C12 0.0218(11) 0.0269(11) 0.0337(11) 0.0055(9) 0.0040(9) 0.0033(9) C13 0.0230(11) 0.0283(11) 0.0271(10) 0.0060(8) 0.0097(8) 0.0036(9) C14 0.0386(14) 0.0255(11) 0.0397(12) 0.0064(9) 0.0091(10) 0.0056(10) C15 0.0369(14) 0.0297(12) 0.0402(12) 0.0029(9) 0.0044(10) 0.0004(10) C16 0.0261(12) 0.0282(11) 0.0355(12) 0.0030(9) 0.0053(9) 0.0038(9) C17 0.0398(13) 0.0298(11) 0.0232(10) -0.0023(8) 0.0047(9) 0.0067(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.221(2) . ? O2 C2 1.217(2) . ? O3 C6 1.229(2) . ? N1 C1 1.381(2) . ? N1 C2 1.391(2) . ? N1 C17 1.457(2) . ? N2 C6 1.344(2) . ? N2 C5 1.451(2) . ? N2 H1X 0.865(18) . ? C1 C4 1.514(2) . ? C2 C3 1.508(3) . ? C3 C4 1.538(2) . ? C3 C10 1.556(3) . ? C3 H3 1.0000 . ? C4 C5 1.543(2) . ? C4 H4 1.0000 . ? C5 C8 1.505(3) . ? C5 H5 1.0000 . ? C6 C7 1.503(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.330(3) . ? C8 H8 0.9500 . ? C9 C16 1.495(3) . ? C9 C10 1.532(2) . ? C10 C11 1.530(3) . ? C10 H10 1.0000 . ? C11 C12 1.505(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.331(3) . ? C12 H12 0.9500 . ? C13 C15 1.496(3) . ? C13 C14 1.507(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 112.18(16) . . ? C1 N1 C17 124.50(16) . . ? C2 N1 C17 123.20(16) . . ? C6 N2 C5 122.93(16) . . ? C6 N2 H1X 121.7(12) . . ? C5 N2 H1X 115.3(12) . . ? O1 C1 N1 123.86(17) . . ? O1 C1 C4 127.70(18) . . ? N1 C1 C4 108.43(16) . . ? O2 C2 N1 122.76(17) . . ? O2 C2 C3 128.01(17) . . ? N1 C2 C3 109.23(15) . . ? C2 C3 C4 103.33(14) . . ? C2 C3 C10 113.67(16) . . ? C4 C3 C10 113.57(14) . . ? C2 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C10 C3 H3 108.7 . . ? C1 C4 C3 104.95(15) . . ? C1 C4 C5 111.71(14) . . ? C3 C4 C5 112.49(15) . . ? C1 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? N2 C5 C8 113.50(14) . . ? N2 C5 C4 110.98(15) . . ? C8 C5 C4 107.81(15) . . ? N2 C5 H5 108.1 . . ? C8 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? O3 C6 N2 121.91(18) . . ? O3 C6 C7 121.50(17) . . ? N2 C6 C7 116.59(16) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C5 120.40(16) . . ? C9 C8 H8 119.8 . . ? C5 C8 H8 119.8 . . ? C8 C9 C16 123.13(16) . . ? C8 C9 C10 115.93(17) . . ? C16 C9 C10 120.91(16) . . ? C11 C10 C9 114.74(16) . . ? C11 C10 C3 114.14(15) . . ? C9 C10 C3 110.68(15) . . ? C11 C10 H10 105.4 . . ? C9 C10 H10 105.4 . . ? C3 C10 H10 105.4 . . ? C12 C11 C10 113.11(17) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 128.47(18) . . ? C13 C12 H12 115.8 . . ? C11 C12 H12 115.8 . . ? C12 C13 C15 124.62(17) . . ? C12 C13 C14 121.01(17) . . ? C15 C13 C14 114.37(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C16 H16A 109.5 . . ? C9 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C9 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C2 N1 C1 O1 179.69(17) . . . . ? C17 N1 C1 O1 3.5(3) . . . . ? C2 N1 C1 C4 1.0(2) . . . . ? C17 N1 C1 C4 -175.25(16) . . . . ? C1 N1 C2 O2 -171.35(16) . . . . ? C17 N1 C2 O2 4.9(3) . . . . ? C1 N1 C2 C3 8.0(2) . . . . ? C17 N1 C2 C3 -175.75(16) . . . . ? O2 C2 C3 C4 166.22(18) . . . . ? N1 C2 C3 C4 -13.06(19) . . . . ? O2 C2 C3 C10 -70.2(2) . . . . ? N1 C2 C3 C10 110.48(17) . . . . ? O1 C1 C4 C3 172.20(18) . . . . ? N1 C1 C4 C3 -9.13(18) . . . . ? O1 C1 C4 C5 50.0(3) . . . . ? N1 C1 C4 C5 -131.31(16) . . . . ? C2 C3 C4 C1 13.01(17) . . . . ? C10 C3 C4 C1 -110.60(16) . . . . ? C2 C3 C4 C5 134.68(15) . . . . ? C10 C3 C4 C5 11.1(2) . . . . ? C6 N2 C5 C8 95.5(2) . . . . ? C6 N2 C5 C4 -142.85(17) . . . . ? C1 C4 C5 N2 -60.1(2) . . . . ? C3 C4 C5 N2 -177.82(14) . . . . ? C1 C4 C5 C8 64.79(19) . . . . ? C3 C4 C5 C8 -52.95(19) . . . . ? C5 N2 C6 O3 1.7(3) . . . . ? C5 N2 C6 C7 -178.80(16) . . . . ? N2 C5 C8 C9 171.20(16) . . . . ? C4 C5 C8 C9 47.8(2) . . . . ? C5 C8 C9 C16 -178.26(17) . . . . ? C5 C8 C9 C10 3.8(2) . . . . ? C8 C9 C10 C11 -179.40(17) . . . . ? C16 C9 C10 C11 2.6(2) . . . . ? C8 C9 C10 C3 -48.5(2) . . . . ? C16 C9 C10 C3 133.50(18) . . . . ? C2 C3 C10 C11 51.9(2) . . . . ? C4 C3 C10 C11 169.71(16) . . . . ? C2 C3 C10 C9 -79.31(19) . . . . ? C4 C3 C10 C9 38.5(2) . . . . ? C9 C10 C11 C12 -176.56(16) . . . . ? C3 C10 C11 C12 54.2(2) . . . . ? C10 C11 C12 C13 108.4(2) . . . . ? C11 C12 C13 C15 -0.5(3) . . . . ? C11 C12 C13 C14 179.29(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.477 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.052 # Attachment 'rob453.cif' data_rob453 _database_code_depnum_ccdc_archive 'CCDC 832712' #TrackingRef 'rob453.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H15 Br N2 O3' _chemical_formula_sum 'C12 H15 Br N2 O3' _chemical_formula_weight 315.17 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' Br Br -0.2901 2.4595 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8021(12) _cell_length_b 10.5357(7) _cell_length_c 13.5435(12) _cell_angle_alpha 90.00 _cell_angle_beta 124.200(6) _cell_angle_gamma 90.00 _cell_volume 1274.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6562 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.99 _exptl_crystal_description 'part of a platelet' _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.227 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6562 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2769 _reflns_number_gt 2063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2769 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Br1 Br 0.24099(4) -0.07933(3) -0.46469(3) 0.02326(12) Uani 1 1 d . . . O1 O 0.2388(3) 0.15041(17) -0.26047(19) 0.0235(5) Uani 1 1 d . . . O2 O 0.4398(3) -0.29656(18) -0.12003(19) 0.0232(5) Uani 1 1 d . . . O3 O 0.0189(3) -0.53765(19) -0.3214(2) 0.0254(5) Uani 1 1 d . . . N1 N 0.3299(3) -0.0487(2) -0.2062(2) 0.0186(6) Uani 1 1 d . . . H1 H 0.402(4) -0.084(3) -0.176(3) 0.014(10) Uiso 1 1 d . . . N2 N 0.2474(3) -0.4385(2) -0.2178(2) 0.0169(6) Uani 1 1 d . . . C1 C 0.1342(4) -0.1474(3) -0.4035(3) 0.0173(7) Uani 1 1 d . . . C2 C 0.1851(4) -0.1088(2) -0.2777(3) 0.0163(7) Uani 1 1 d . . . H2 H 0.1098 -0.0472 -0.2853 0.020 Uiso 1 1 calc R . . C3 C 0.3468(4) 0.0783(3) -0.2054(3) 0.0179(7) Uani 1 1 d . . . C4 C 0.5040(4) 0.1270(3) -0.1335(3) 0.0252(8) Uani 1 1 d . . . H4A H 0.5249 0.1718 -0.1860 0.038 Uiso 1 1 calc R . . H4B H 0.5735 0.0556 -0.0953 0.038 Uiso 1 1 calc R . . H4C H 0.5167 0.1854 -0.0722 0.038 Uiso 1 1 calc R . . C5 C 0.1800(3) -0.2275(2) -0.2127(3) 0.0165(7) Uani 1 1 d . . . H5 H 0.1886 -0.1987 -0.1387 0.020 Uiso 1 1 calc R . . C6 C 0.3075(4) -0.3192(3) -0.1765(3) 0.0190(7) Uani 1 1 d . . . C7 C 0.0925(4) -0.4413(3) -0.2809(3) 0.0204(7) Uani 1 1 d . . . C8 C 0.0357(3) -0.3077(3) -0.2873(3) 0.0168(7) Uani 1 1 d . . . H8 H -0.0182 -0.3067 -0.2468 0.020 Uiso 1 1 calc R . . C9 C -0.0716(3) -0.2571(3) -0.4166(3) 0.0196(7) Uani 1 1 d . . . H9 H -0.1162 -0.1773 -0.4096 0.024 Uiso 1 1 calc R . . C10 C 0.0156(4) -0.2186(3) -0.4680(3) 0.0206(7) Uani 1 1 d . . . H10 H -0.0151 -0.2454 -0.5455 0.025 Uiso 1 1 calc R . . C11 C -0.2026(4) -0.3445(3) -0.4980(3) 0.0297(8) Uani 1 1 d . . . H11A H -0.2729 -0.3010 -0.5736 0.044 Uiso 1 1 calc R . . H11B H -0.2536 -0.3672 -0.4593 0.044 Uiso 1 1 calc R . . H11C H -0.1656 -0.4217 -0.5137 0.044 Uiso 1 1 calc R . . C12 C 0.3404(4) -0.5517(3) -0.1869(3) 0.0237(8) Uani 1 1 d . . . H12A H 0.4130 -0.5383 -0.2076 0.036 Uiso 1 1 calc R . . H12B H 0.2768 -0.6246 -0.2314 0.036 Uiso 1 1 calc R . . H12C H 0.3936 -0.5680 -0.1011 0.036 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 Br1 0.0281(2) 0.02237(19) 0.0261(2) 0.00030(14) 0.01940(17) -0.00154(14) O1 0.0254(15) 0.0136(11) 0.0306(13) 0.0018(9) 0.0152(12) 0.0016(10) O2 0.0180(14) 0.0173(11) 0.0299(13) 0.0001(9) 0.0107(12) -0.0004(10) O3 0.0256(14) 0.0172(11) 0.0330(14) -0.0025(9) 0.0162(12) -0.0062(10) N1 0.0171(17) 0.0141(14) 0.0220(15) 0.0013(11) 0.0094(14) 0.0015(12) N2 0.0187(15) 0.0127(12) 0.0212(14) 0.0009(10) 0.0124(13) 0.0013(11) C1 0.0190(19) 0.0141(15) 0.0231(17) 0.0041(12) 0.0145(16) 0.0030(13) C2 0.0164(18) 0.0146(15) 0.0192(17) 0.0029(11) 0.0108(15) 0.0008(12) C3 0.0231(19) 0.0153(15) 0.0183(16) -0.0035(13) 0.0134(15) -0.0020(15) C4 0.024(2) 0.0191(16) 0.0277(19) -0.0031(13) 0.0117(17) -0.0047(14) C5 0.0236(19) 0.0136(14) 0.0180(16) -0.0024(12) 0.0152(15) 0.0004(13) C6 0.027(2) 0.0155(15) 0.0175(17) 0.0010(12) 0.0146(16) 0.0003(14) C7 0.026(2) 0.0199(17) 0.0224(17) -0.0002(13) 0.0178(16) -0.0027(14) C8 0.0168(18) 0.0151(15) 0.0226(17) -0.0001(12) 0.0136(15) -0.0001(12) C9 0.0170(18) 0.0189(15) 0.0226(18) 0.0004(13) 0.0109(15) -0.0006(13) C10 0.025(2) 0.0177(16) 0.0210(17) 0.0036(12) 0.0139(16) 0.0024(13) C11 0.024(2) 0.038(2) 0.0243(19) -0.0003(15) 0.0116(17) -0.0066(16) C12 0.026(2) 0.0154(16) 0.0305(19) 0.0011(13) 0.0164(17) 0.0025(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.899(3) . ? O1 C3 1.231(4) . ? O2 C6 1.207(4) . ? O3 C7 1.213(3) . ? N1 C3 1.350(4) . ? N1 C2 1.443(4) . ? N1 H1 0.75(3) . ? N2 C6 1.380(4) . ? N2 C7 1.387(4) . ? N2 C12 1.460(4) . ? C1 C10 1.308(4) . ? C1 C2 1.523(4) . ? C2 C5 1.548(4) . ? C2 H2 1.0000 . ? C3 C4 1.496(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.521(4) . ? C5 C8 1.547(4) . ? C5 H5 1.0000 . ? C7 C8 1.519(4) . ? C8 C9 1.552(4) . ? C8 H8 1.0000 . ? C9 C10 1.508(4) . ? C9 C11 1.521(4) . ? C9 H9 1.0000 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C2 122.1(3) . . ? C3 N1 H1 114(2) . . ? C2 N1 H1 123(2) . . ? C6 N2 C7 113.5(2) . . ? C6 N2 C12 122.5(3) . . ? C7 N2 C12 123.8(2) . . ? C10 C1 C2 120.1(3) . . ? C10 C1 Br1 122.2(2) . . ? C2 C1 Br1 117.5(2) . . ? N1 C2 C1 116.2(3) . . ? N1 C2 C5 110.2(2) . . ? C1 C2 C5 108.4(2) . . ? N1 C2 H2 107.2 . . ? C1 C2 H2 107.2 . . ? C5 C2 H2 107.2 . . ? O1 C3 N1 121.9(3) . . ? O1 C3 C4 121.7(3) . . ? N1 C3 C4 116.4(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C8 105.1(2) . . ? C6 C5 C2 112.4(2) . . ? C8 C5 C2 114.5(2) . . ? C6 C5 H5 108.2 . . ? C8 C5 H5 108.2 . . ? C2 C5 H5 108.2 . . ? O2 C6 N2 123.8(3) . . ? O2 C6 C5 127.9(3) . . ? N2 C6 C5 108.3(3) . . ? O3 C7 N2 123.6(3) . . ? O3 C7 C8 127.5(3) . . ? N2 C7 C8 108.9(2) . . ? C7 C8 C5 104.0(2) . . ? C7 C8 C9 113.8(2) . . ? C5 C8 C9 112.9(2) . . ? C7 C8 H8 108.6 . . ? C5 C8 H8 108.6 . . ? C9 C8 H8 108.6 . . ? C10 C9 C11 113.3(2) . . ? C10 C9 C8 110.4(3) . . ? C11 C9 C8 114.3(2) . . ? C10 C9 H9 106.0 . . ? C11 C9 H9 106.0 . . ? C8 C9 H9 106.0 . . ? C1 C10 C9 118.6(3) . . ? C1 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C3 N1 C2 C1 90.1(3) . . . . ? C3 N1 C2 C5 -146.2(3) . . . . ? C10 C1 C2 N1 170.0(3) . . . . ? Br1 C1 C2 N1 -14.1(3) . . . . ? C10 C1 C2 C5 45.3(4) . . . . ? Br1 C1 C2 C5 -138.7(2) . . . . ? C2 N1 C3 O1 4.1(4) . . . . ? C2 N1 C3 C4 -176.1(3) . . . . ? N1 C2 C5 C6 -53.8(3) . . . . ? C1 C2 C5 C6 74.3(3) . . . . ? N1 C2 C5 C8 -173.7(2) . . . . ? C1 C2 C5 C8 -45.5(3) . . . . ? C7 N2 C6 O2 -179.7(3) . . . . ? C12 N2 C6 O2 6.0(4) . . . . ? C7 N2 C6 C5 1.3(3) . . . . ? C12 N2 C6 C5 -173.0(2) . . . . ? C8 C5 C6 O2 177.9(3) . . . . ? C2 C5 C6 O2 52.7(4) . . . . ? C8 C5 C6 N2 -3.2(3) . . . . ? C2 C5 C6 N2 -128.3(2) . . . . ? C6 N2 C7 O3 -177.7(3) . . . . ? C12 N2 C7 O3 -3.5(5) . . . . ? C6 N2 C7 C8 1.3(3) . . . . ? C12 N2 C7 C8 175.4(3) . . . . ? O3 C7 C8 C5 175.8(3) . . . . ? N2 C7 C8 C5 -3.1(3) . . . . ? O3 C7 C8 C9 -61.0(4) . . . . ? N2 C7 C8 C9 120.1(3) . . . . ? C6 C5 C8 C7 3.7(3) . . . . ? C2 C5 C8 C7 127.6(3) . . . . ? C6 C5 C8 C9 -120.2(2) . . . . ? C2 C5 C8 C9 3.7(3) . . . . ? C7 C8 C9 C10 -76.4(3) . . . . ? C5 C8 C9 C10 41.9(3) . . . . ? C7 C8 C9 C11 52.8(4) . . . . ? C5 C8 C9 C11 171.1(2) . . . . ? C2 C1 C10 C9 2.1(4) . . . . ? Br1 C1 C10 C9 -173.7(2) . . . . ? C11 C9 C10 C1 -177.4(3) . . . . ? C8 C9 C10 C1 -47.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.542 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.093 # Attachment 'rob468.cif' data_rob468 _database_code_depnum_ccdc_archive 'CCDC 832713' #TrackingRef 'rob468.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O3' _chemical_formula_sum 'C16 H20 N2 O3' _chemical_formula_weight 288.34 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9261(5) _cell_length_b 17.9405(14) _cell_length_c 15.2365(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.061(4) _cell_angle_gamma 90.00 _cell_volume 3241.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15743 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15743 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7009 _reflns_number_gt 3810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0489P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7009 _refine_ls_number_parameters 393 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _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 0.54635(10) 0.31492(8) 0.06186(9) 0.0360(4) Uani 1 1 d . . . O2 O 0.54363(11) 0.21406(9) -0.01659(9) 0.0510(4) Uani 1 1 d . . . O3 O 0.38496(10) 0.18537(8) 0.15176(9) 0.0408(4) Uani 1 1 d . . . N1 N 0.58099(12) 0.25248(11) 0.04639(11) 0.0321(4) Uani 1 1 d . . . N2 N 0.54416(11) 0.22644(10) 0.22979(10) 0.0265(4) Uani 1 1 d . . . C1 C 0.67236(13) 0.21866(11) 0.11005(12) 0.0275(5) Uani 1 1 d . . . H1 H 0.7132 0.1807 0.0773 0.033 Uiso 1 1 calc R . . C2 C 0.61704(14) 0.17817(11) 0.18345(11) 0.0277(5) Uani 1 1 d . . . H2 H 0.5700 0.1366 0.1557 0.033 Uiso 1 1 calc R . . C3 C 0.43107(14) 0.22638(12) 0.20956(13) 0.0308(5) Uani 1 1 d . . . C4 C 0.36529(14) 0.28020(12) 0.25938(13) 0.0378(5) Uani 1 1 d . . . H4A H 0.3441 0.3235 0.2221 0.057 Uiso 1 1 calc R . . H4B H 0.4117 0.2966 0.3128 0.057 Uiso 1 1 calc R . . H4C H 0.2971 0.2557 0.2758 0.057 Uiso 1 1 calc R . . C5 C 0.70760(15) 0.14473(11) 0.24771(12) 0.0287(5) Uani 1 1 d . . . C6 C 0.81206(15) 0.17101(12) 0.25380(12) 0.0345(5) Uani 1 1 d . . . H6 H 0.8659 0.1469 0.2946 0.041 Uiso 1 1 calc R . . C7 C 0.85368(14) 0.23480(12) 0.20300(12) 0.0343(5) Uani 1 1 d . . . H7 H 0.9045 0.2137 0.1611 0.041 Uiso 1 1 calc R . . C8 C 0.75769(13) 0.27679(11) 0.14729(11) 0.0266(5) Uani 1 1 d . . . H8 H 0.7197 0.3100 0.1878 0.032 Uiso 1 1 calc R . . C9 C 0.80437(13) 0.32543(12) 0.07789(12) 0.0265(5) Uani 1 1 d . . . C10 C 0.86277(14) 0.29398(12) 0.01229(12) 0.0324(5) Uani 1 1 d . . . H10 H 0.8693 0.2413 0.0084 0.039 Uiso 1 1 calc R . . C11 C 0.91140(15) 0.33910(13) -0.04730(13) 0.0343(5) Uani 1 1 d . . . H11 H 0.9517 0.3170 -0.0912 0.041 Uiso 1 1 calc R . . C12 C 0.90184(14) 0.41552(12) -0.04348(13) 0.0338(5) Uani 1 1 d . . . H12 H 0.9353 0.4462 -0.0844 0.041 Uiso 1 1 calc R . . C13 C 0.84287(14) 0.44712(12) 0.02059(13) 0.0376(5) Uani 1 1 d . . . H13 H 0.8349 0.4997 0.0234 0.045 Uiso 1 1 calc R . . C14 C 0.79528(14) 0.40201(12) 0.08078(13) 0.0334(5) Uani 1 1 d . . . H14 H 0.7556 0.4244 0.1249 0.040 Uiso 1 1 calc R . . C15 C 0.92340(17) 0.28823(15) 0.26363(15) 0.0611(8) Uani 1 1 d . . . H15A H 0.8756 0.3108 0.3049 0.092 Uiso 1 1 calc R . . H15B H 0.9544 0.3274 0.2284 0.092 Uiso 1 1 calc R . . H15C H 0.9853 0.2610 0.2968 0.092 Uiso 1 1 calc R . . C16 C 0.67084(16) 0.08326(12) 0.30512(12) 0.0369(5) Uani 1 1 d . . . H16A H 0.7360 0.0651 0.3438 0.055 Uiso 1 1 calc R . . H16B H 0.6389 0.0423 0.2679 0.055 Uiso 1 1 calc R . . H16C H 0.6137 0.1023 0.3411 0.055 Uiso 1 1 calc R . . O4 O 0.07258(9) 0.16777(8) 0.11800(9) 0.0332(3) Uani 1 1 d . . . O5 O -0.04969(9) 0.10658(8) 0.03068(9) 0.0429(4) Uani 1 1 d . . . O6 O 0.12765(10) 0.18837(8) -0.11633(9) 0.0425(4) Uani 1 1 d . . . N3 N 0.04333(12) 0.11294(10) 0.07380(10) 0.0299(4) Uani 1 1 d . . . N4 N 0.24196(12) 0.14471(10) 0.00004(11) 0.0273(4) Uani 1 1 d . . . C17 C 0.12595(13) 0.05035(11) 0.06886(12) 0.0265(5) Uani 1 1 d . . . H17 H 0.0827 0.0038 0.0520 0.032 Uiso 1 1 calc R . . C18 C 0.20030(14) 0.06887(11) -0.00507(12) 0.0290(5) Uani 1 1 d . . . H18 H 0.1528 0.0631 -0.0628 0.035 Uiso 1 1 calc R . . C19 C 0.19862(15) 0.20011(12) -0.05232(13) 0.0322(5) Uani 1 1 d . . . C20 C 0.24122(15) 0.27657(12) -0.02729(13) 0.0387(5) Uani 1 1 d . . . H20A H 0.2711 0.3000 -0.0781 0.058 Uiso 1 1 calc R . . H20B H 0.3012 0.2729 0.0217 0.058 Uiso 1 1 calc R . . H20C H 0.1793 0.3068 -0.0091 0.058 Uiso 1 1 calc R . . C21 C 0.29606(14) 0.01367(12) -0.00343(13) 0.0322(5) Uani 1 1 d . . . C22 C 0.32349(14) -0.02998(12) 0.06533(14) 0.0355(5) Uani 1 1 d . . . H22 H 0.3836 -0.0641 0.0609 0.043 Uiso 1 1 calc R . . C23 C 0.26920(14) -0.03103(12) 0.14958(13) 0.0354(5) Uani 1 1 d . . . H23 H 0.2203 -0.0764 0.1490 0.043 Uiso 1 1 calc R . . C24 C 0.19395(13) 0.03750(11) 0.15829(12) 0.0273(5) Uani 1 1 d . . . H24 H 0.2436 0.0818 0.1722 0.033 Uiso 1 1 calc R . . C25 C 0.11840(13) 0.02812(11) 0.23207(13) 0.0286(5) Uani 1 1 d . . . C26 C 0.13214(14) 0.07183(12) 0.30700(12) 0.0346(5) Uani 1 1 d . . . H26 H 0.1872 0.1103 0.3113 0.041 Uiso 1 1 calc R . . C27 C 0.06696(15) 0.06050(13) 0.37607(13) 0.0415(6) Uani 1 1 d . . . H27 H 0.0778 0.0909 0.4273 0.050 Uiso 1 1 calc R . . C28 C -0.01372(16) 0.00494(14) 0.37038(15) 0.0449(6) Uani 1 1 d . . . H28 H -0.0579 -0.0033 0.4178 0.054 Uiso 1 1 calc R . . C29 C -0.02974(15) -0.03855(13) 0.29543(15) 0.0433(6) Uani 1 1 d . . . H29 H -0.0856 -0.0765 0.2910 0.052 Uiso 1 1 calc R . . C30 C 0.03581(14) -0.02698(12) 0.22619(13) 0.0359(5) Uani 1 1 d . . . H30 H 0.0240 -0.0569 0.1746 0.043 Uiso 1 1 calc R . . C31 C 0.35807(16) -0.03675(15) 0.22946(14) 0.0548(7) Uani 1 1 d . . . H31A H 0.4037 -0.0817 0.2242 0.082 Uiso 1 1 calc R . . H31B H 0.3206 -0.0396 0.2836 0.082 Uiso 1 1 calc R . . H31C H 0.4069 0.0073 0.2318 0.082 Uiso 1 1 calc R . . C32 C 0.35506(17) 0.01338(14) -0.08586(14) 0.0546(7) Uani 1 1 d . . . H32A H 0.4191 -0.0211 -0.0784 0.082 Uiso 1 1 calc R . . H32B H 0.3822 0.0637 -0.0969 0.082 Uiso 1 1 calc R . . H32C H 0.3023 -0.0027 -0.1360 0.082 Uiso 1 1 calc R . . H1X H 0.2902(16) 0.1580(12) 0.0486(13) 0.049(6) Uiso 1 1 d . . . H2X H 0.5739(15) 0.2524(12) 0.2774(13) 0.045(6) 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 0.0340(7) 0.0320(10) 0.0417(9) 0.0035(8) 0.0021(6) 0.0042(7) O2 0.0631(9) 0.0557(12) 0.0307(9) -0.0108(8) -0.0116(7) -0.0024(8) O3 0.0387(7) 0.0456(11) 0.0354(8) -0.0037(8) -0.0090(6) -0.0127(7) N1 0.0357(9) 0.0352(12) 0.0251(10) 0.0013(9) 0.0029(7) -0.0047(9) N2 0.0246(8) 0.0301(11) 0.0242(10) -0.0054(8) -0.0006(7) -0.0019(7) C1 0.0312(10) 0.0269(12) 0.0238(11) -0.0008(9) -0.0003(8) 0.0035(9) C2 0.0343(10) 0.0258(12) 0.0231(10) -0.0042(9) 0.0035(8) -0.0013(9) C3 0.0323(11) 0.0310(14) 0.0280(12) 0.0083(10) -0.0017(8) -0.0065(10) C4 0.0269(10) 0.0384(15) 0.0480(13) 0.0050(11) 0.0045(9) 0.0045(10) C5 0.0372(11) 0.0263(13) 0.0236(11) -0.0029(9) 0.0075(8) 0.0071(9) C6 0.0375(11) 0.0408(15) 0.0255(11) 0.0049(10) 0.0049(8) 0.0147(10) C7 0.0292(10) 0.0480(16) 0.0258(11) 0.0072(11) 0.0030(8) 0.0041(10) C8 0.0281(9) 0.0287(13) 0.0235(11) -0.0025(9) 0.0051(8) 0.0022(9) C9 0.0236(9) 0.0286(13) 0.0270(11) -0.0032(10) 0.0016(8) 0.0020(9) C10 0.0398(11) 0.0279(13) 0.0297(12) -0.0019(10) 0.0053(9) 0.0039(9) C11 0.0374(11) 0.0374(15) 0.0297(12) -0.0041(11) 0.0114(9) 0.0031(10) C12 0.0319(10) 0.0369(15) 0.0336(12) 0.0018(11) 0.0076(8) -0.0046(10) C13 0.0383(11) 0.0253(13) 0.0503(14) -0.0045(11) 0.0099(10) -0.0008(10) C14 0.0326(10) 0.0335(15) 0.0364(13) -0.0082(11) 0.0136(9) -0.0018(10) C15 0.0523(13) 0.081(2) 0.0455(15) 0.0166(14) -0.0145(11) -0.0294(14) C16 0.0492(12) 0.0326(14) 0.0289(12) -0.0003(10) 0.0044(9) 0.0036(10) O4 0.0323(7) 0.0264(9) 0.0409(9) -0.0095(7) 0.0033(6) 0.0019(6) O5 0.0270(7) 0.0377(10) 0.0596(10) -0.0095(8) -0.0161(6) 0.0056(6) O6 0.0401(7) 0.0502(11) 0.0339(8) 0.0116(8) -0.0112(6) -0.0025(7) N3 0.0276(9) 0.0293(11) 0.0322(10) -0.0033(9) 0.0004(7) 0.0023(8) N4 0.0285(8) 0.0302(11) 0.0225(9) -0.0004(8) -0.0011(7) 0.0017(8) C17 0.0227(9) 0.0211(12) 0.0349(12) -0.0065(9) -0.0011(8) 0.0040(8) C18 0.0296(10) 0.0302(13) 0.0258(11) -0.0068(10) -0.0034(8) 0.0004(9) C19 0.0292(10) 0.0405(15) 0.0276(12) 0.0049(11) 0.0057(9) 0.0038(10) C20 0.0406(11) 0.0361(15) 0.0390(13) 0.0064(11) 0.0023(9) -0.0020(10) C21 0.0292(10) 0.0327(14) 0.0340(13) -0.0107(11) -0.0004(8) 0.0018(9) C22 0.0256(10) 0.0304(14) 0.0499(15) -0.0091(11) 0.0011(9) 0.0062(9) C23 0.0302(10) 0.0311(14) 0.0449(13) 0.0063(11) 0.0033(9) 0.0050(9) C24 0.0264(9) 0.0240(12) 0.0308(12) -0.0005(9) -0.0007(8) -0.0011(9) C25 0.0232(9) 0.0289(13) 0.0328(12) 0.0064(10) -0.0014(8) 0.0017(9) C26 0.0313(10) 0.0390(15) 0.0325(13) 0.0023(11) -0.0009(9) -0.0021(10) C27 0.0425(12) 0.0515(17) 0.0303(13) 0.0022(11) 0.0028(9) 0.0049(12) C28 0.0392(12) 0.0539(17) 0.0428(15) 0.0169(13) 0.0106(10) 0.0057(12) C29 0.0339(11) 0.0428(16) 0.0534(16) 0.0104(13) 0.0056(10) -0.0027(10) C30 0.0313(10) 0.0335(14) 0.0427(14) 0.0015(11) 0.0025(9) 0.0016(10) C31 0.0413(12) 0.069(2) 0.0524(16) 0.0147(14) -0.0014(10) 0.0230(12) C32 0.0584(13) 0.0632(19) 0.0438(15) -0.0131(13) 0.0131(11) 0.0179(13) _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 N1 1.225(2) . ? O2 N1 1.227(2) . ? O3 C3 1.232(2) . ? N1 C1 1.508(2) . ? N2 C3 1.351(2) . ? N2 C2 1.461(2) . ? N2 H2X 0.90(2) . ? C1 C8 1.524(2) . ? C1 C2 1.539(2) . ? C1 H1 1.0000 . ? C2 C5 1.504(2) . ? C2 H2 1.0000 . ? C3 C4 1.500(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.326(2) . ? C5 C16 1.501(3) . ? C6 C7 1.495(3) . ? C6 H6 0.9500 . ? C7 C15 1.517(3) . ? C7 C8 1.547(2) . ? C7 H7 1.0000 . ? C8 C9 1.521(3) . ? C8 H8 1.0000 . ? C9 C14 1.379(3) . ? C9 C10 1.396(2) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.378(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O4 N3 1.2221(18) . ? O5 N3 1.2335(17) . ? O6 C19 1.240(2) . ? N3 C17 1.501(2) . ? N4 C19 1.343(2) . ? N4 C18 1.448(2) . ? N4 H1X 0.92(2) . ? C17 C24 1.528(2) . ? C17 C18 1.542(2) . ? C17 H17 1.0000 . ? C18 C21 1.510(3) . ? C18 H18 1.0000 . ? C19 C20 1.498(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.321(3) . ? C21 C32 1.503(3) . ? C22 C23 1.498(3) . ? C22 H22 0.9500 . ? C23 C31 1.531(3) . ? C23 C24 1.536(3) . ? C23 H23 1.0000 . ? C24 C25 1.522(2) . ? C24 H24 1.0000 . ? C25 C26 1.380(3) . ? C25 C30 1.392(3) . ? C26 C27 1.388(2) . ? C26 H26 0.9500 . ? C27 C28 1.382(3) . ? C27 H27 0.9500 . ? C28 C29 1.380(3) . ? C28 H28 0.9500 . ? C29 C30 1.393(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 O2 124.22(17) . . ? O1 N1 C1 118.66(16) . . ? O2 N1 C1 117.08(17) . . ? C3 N2 C2 121.33(17) . . ? C3 N2 H2X 118.8(12) . . ? C2 N2 H2X 119.4(12) . . ? N1 C1 C8 111.89(16) . . ? N1 C1 C2 108.74(13) . . ? C8 C1 C2 111.89(14) . . ? N1 C1 H1 108.1 . . ? C8 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? N2 C2 C5 110.18(14) . . ? N2 C2 C1 113.21(16) . . ? C5 C2 C1 109.14(14) . . ? N2 C2 H2 108.1 . . ? C5 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? O3 C3 N2 121.53(19) . . ? O3 C3 C4 121.91(16) . . ? N2 C3 C4 116.54(17) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C16 123.39(18) . . ? C6 C5 C2 120.56(18) . . ? C16 C5 C2 116.01(16) . . ? C5 C6 C7 126.63(18) . . ? C5 C6 H6 116.7 . . ? C7 C6 H6 116.7 . . ? C6 C7 C15 111.03(16) . . ? C6 C7 C8 112.95(14) . . ? C15 C7 C8 110.65(18) . . ? C6 C7 H7 107.3 . . ? C15 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? C9 C8 C1 114.37(15) . . ? C9 C8 C7 110.91(13) . . ? C1 C8 C7 107.30(15) . . ? C9 C8 H8 108.0 . . ? C1 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C14 C9 C10 118.18(18) . . ? C14 C9 C8 120.89(16) . . ? C10 C9 C8 120.85(18) . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.70(18) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.22(18) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 121.36(17) . . ? C9 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C7 C15 H15A 109.5 . . ? C7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C5 C16 H16A 109.5 . . ? C5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 N3 O5 123.81(16) . . ? O4 N3 C17 118.63(14) . . ? O5 N3 C17 117.54(16) . . ? C19 N4 C18 123.71(16) . . ? C19 N4 H1X 117.1(14) . . ? C18 N4 H1X 118.0(14) . . ? N3 C17 C24 110.95(15) . . ? N3 C17 C18 107.86(15) . . ? C24 C17 C18 113.08(13) . . ? N3 C17 H17 108.3 . . ? C24 C17 H17 108.3 . . ? C18 C17 H17 108.3 . . ? N4 C18 C21 111.15(14) . . ? N4 C18 C17 112.57(15) . . ? C21 C18 C17 109.82(16) . . ? N4 C18 H18 107.7 . . ? C21 C18 H18 107.7 . . ? C17 C18 H18 107.7 . . ? O6 C19 N4 122.0(2) . . ? O6 C19 C20 122.73(19) . . ? N4 C19 C20 115.30(17) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C32 124.20(18) . . ? C22 C21 C18 121.69(17) . . ? C32 C21 C18 114.11(18) . . ? C21 C22 C23 126.44(18) . . ? C21 C22 H22 116.8 . . ? C23 C22 H22 116.8 . . ? C22 C23 C31 110.90(15) . . ? C22 C23 C24 111.92(16) . . ? C31 C23 C24 110.29(17) . . ? C22 C23 H23 107.9 . . ? C31 C23 H23 107.9 . . ? C24 C23 H23 107.9 . . ? C25 C24 C17 112.05(13) . . ? C25 C24 C23 111.84(16) . . ? C17 C24 C23 107.67(15) . . ? C25 C24 H24 108.4 . . ? C17 C24 H24 108.4 . . ? C23 C24 H24 108.4 . . ? C26 C25 C30 118.57(17) . . ? C26 C25 C24 121.33(17) . . ? C30 C25 C24 120.07(18) . . ? C25 C26 C27 121.12(19) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C28 C27 C26 120.0(2) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C29 C28 C27 119.64(19) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 120.2(2) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 120.5(2) . . ? C25 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C23 C31 H31A 109.5 . . ? C23 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C23 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C21 C32 H32A 109.5 . . ? C21 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C21 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 N1 C1 C8 -37.0(2) . . . . ? O2 N1 C1 C8 145.29(16) . . . . ? O1 N1 C1 C2 87.13(19) . . . . ? O2 N1 C1 C2 -90.60(19) . . . . ? C3 N2 C2 C5 -138.40(17) . . . . ? C3 N2 C2 C1 99.1(2) . . . . ? N1 C1 C2 N2 -56.5(2) . . . . ? C8 C1 C2 N2 67.64(18) . . . . ? N1 C1 C2 C5 -179.57(16) . . . . ? C8 C1 C2 C5 -55.5(2) . . . . ? C2 N2 C3 O3 0.5(3) . . . . ? C2 N2 C3 C4 -177.93(16) . . . . ? N2 C2 C5 C6 -103.1(2) . . . . ? C1 C2 C5 C6 21.8(2) . . . . ? N2 C2 C5 C16 74.7(2) . . . . ? C1 C2 C5 C16 -160.42(16) . . . . ? C16 C5 C6 C7 -176.16(18) . . . . ? C2 C5 C6 C7 1.4(3) . . . . ? C5 C6 C7 C15 132.3(2) . . . . ? C5 C6 C7 C8 7.3(3) . . . . ? N1 C1 C8 C9 -50.3(2) . . . . ? C2 C1 C8 C9 -172.67(15) . . . . ? N1 C1 C8 C7 -173.81(14) . . . . ? C2 C1 C8 C7 63.86(18) . . . . ? C6 C7 C8 C9 -163.67(16) . . . . ? C15 C7 C8 C9 71.2(2) . . . . ? C6 C7 C8 C1 -38.1(2) . . . . ? C15 C7 C8 C1 -163.27(15) . . . . ? C1 C8 C9 C14 123.37(18) . . . . ? C7 C8 C9 C14 -115.13(19) . . . . ? C1 C8 C9 C10 -60.0(2) . . . . ? C7 C8 C9 C10 61.5(2) . . . . ? C14 C9 C10 C11 0.9(3) . . . . ? C8 C9 C10 C11 -175.80(16) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C10 C9 C14 C13 -0.2(3) . . . . ? C8 C9 C14 C13 176.50(16) . . . . ? C12 C13 C14 C9 -0.6(3) . . . . ? O4 N3 C17 C24 39.2(2) . . . . ? O5 N3 C17 C24 -142.68(16) . . . . ? O4 N3 C17 C18 -85.16(19) . . . . ? O5 N3 C17 C18 92.95(18) . . . . ? C19 N4 C18 C21 133.88(17) . . . . ? C19 N4 C18 C17 -102.44(19) . . . . ? N3 C17 C18 N4 46.94(18) . . . . ? C24 C17 C18 N4 -76.1(2) . . . . ? N3 C17 C18 C21 171.35(15) . . . . ? C24 C17 C18 C21 48.3(2) . . . . ? C18 N4 C19 O6 -8.7(3) . . . . ? C18 N4 C19 C20 170.75(15) . . . . ? N4 C18 C21 C22 109.9(2) . . . . ? C17 C18 C21 C22 -15.3(2) . . . . ? N4 C18 C21 C32 -70.3(2) . . . . ? C17 C18 C21 C32 164.50(17) . . . . ? C32 C21 C22 C23 178.8(2) . . . . ? C18 C21 C22 C23 -1.4(3) . . . . ? C21 C22 C23 C31 -137.2(2) . . . . ? C21 C22 C23 C24 -13.5(3) . . . . ? N3 C17 C24 C25 52.1(2) . . . . ? C18 C17 C24 C25 173.47(16) . . . . ? N3 C17 C24 C23 175.52(14) . . . . ? C18 C17 C24 C23 -63.1(2) . . . . ? C22 C23 C24 C25 166.85(15) . . . . ? C31 C23 C24 C25 -69.2(2) . . . . ? C22 C23 C24 C17 43.3(2) . . . . ? C31 C23 C24 C17 167.30(16) . . . . ? C17 C24 C25 C26 -125.72(19) . . . . ? C23 C24 C25 C26 113.3(2) . . . . ? C17 C24 C25 C30 56.4(2) . . . . ? C23 C24 C25 C30 -64.6(2) . . . . ? C30 C25 C26 C27 1.3(3) . . . . ? C24 C25 C26 C27 -176.62(17) . . . . ? C25 C26 C27 C28 -0.3(3) . . . . ? C26 C27 C28 C29 -0.6(3) . . . . ? C27 C28 C29 C30 0.6(3) . . . . ? C26 C25 C30 C29 -1.3(3) . . . . ? C24 C25 C30 C29 176.61(17) . . . . ? C28 C29 C30 C25 0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.201 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.041