# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_don1e _database_code_depnum_ccdc_archive 'CCDC 767841' #TrackingRef 'N-(2S,3S,4R,5S-tetraacetoxycyclohex-1R-yl)phthalimide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O10' _chemical_formula_weight 461.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' 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' '-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 27.7646(12) _cell_length_b 11.6104(5) _cell_length_c 16.3768(7) _cell_angle_alpha 90.00 _cell_angle_beta 123.535(2) _cell_angle_gamma 90.00 _cell_volume 4400.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6453 _cell_measurement_theta_min 4 _cell_measurement_theta_max 67 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6809 _exptl_absorpt_correction_T_max 0.9542 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17563 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 67.98 _reflns_number_total 3843 _reflns_number_gt 3214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)' _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _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^)+(0.0560P)^2^+3.5406P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3843 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 0.26134(5) 0.48664(9) 0.40635(8) 0.0248(3) Uani 1 1 d . . . O2 O 0.23026(5) 0.66546(9) 0.40596(9) 0.0317(3) Uani 1 1 d . . . O3 O 0.16354(5) 0.34929(9) 0.31785(8) 0.0260(3) Uani 1 1 d . . . O4 O 0.15963(6) 0.44859(10) 0.43278(9) 0.0358(3) Uani 1 1 d . . . O5 O 0.06758(5) 0.39333(9) 0.13679(8) 0.0274(3) Uani 1 1 d . . . O6 O 0.03355(6) 0.57142(11) 0.12798(11) 0.0438(4) Uani 1 1 d . . . O7 O 0.10962(5) 0.35614(9) 0.01758(8) 0.0270(3) Uani 1 1 d . . . O8 O 0.12833(5) 0.16943(10) 0.01082(9) 0.0315(3) Uani 1 1 d . . . O9 O 0.29143(5) 0.61210(9) 0.23459(8) 0.0285(3) Uani 1 1 d . . . O10 O 0.34931(5) 0.24821(10) 0.36094(9) 0.0323(3) Uani 1 1 d . . . N1 N 0.30623(6) 0.42478(11) 0.29379(10) 0.0239(3) Uani 1 1 d . . . C1 C 0.24750(7) 0.39559(13) 0.26456(12) 0.0239(3) Uani 1 1 d . . . H1A H 0.2486 0.3196 0.2943 0.029 Uiso 1 1 calc R . . C2 C 0.22357(7) 0.48595(13) 0.30106(11) 0.0232(3) Uani 1 1 d . . . H2A H 0.2239 0.5634 0.2746 0.028 Uiso 1 1 calc R . . C3 C 0.16227(7) 0.45614(13) 0.27104(12) 0.0248(3) Uani 1 1 d . . . H3A H 0.1469 0.5192 0.2921 0.030 Uiso 1 1 calc R . . C4 C 0.12224(7) 0.43887(13) 0.16059(12) 0.0250(3) Uani 1 1 d . . . H4A H 0.1159 0.5142 0.1265 0.030 Uiso 1 1 calc R . . C5 C 0.14657(7) 0.35242(14) 0.12336(11) 0.0243(3) Uani 1 1 d . . . H5A H 0.1465 0.2735 0.1477 0.029 Uiso 1 1 calc R . . C6 C 0.20718(7) 0.38530(13) 0.15340(11) 0.0246(3) Uani 1 1 d . . . H6A H 0.2059 0.4597 0.1228 0.030 Uiso 1 1 calc R . . H6B H 0.2223 0.3262 0.1296 0.030 Uiso 1 1 calc R . . C7 C 0.38534(7) 0.51913(14) 0.31484(12) 0.0262(4) Uani 1 1 d . . . C8 C 0.40305(7) 0.40829(14) 0.35077(12) 0.0274(4) Uani 1 1 d . . . C9 C 0.45885(8) 0.37182(15) 0.38967(13) 0.0329(4) Uani 1 1 d . . . H9A H 0.4706 0.2955 0.4135 0.039 Uiso 1 1 calc R . . C10 C 0.49740(8) 0.45180(16) 0.39263(15) 0.0367(4) Uani 1 1 d . . . H10A H 0.5363 0.4298 0.4193 0.044 Uiso 1 1 calc R . . C11 C 0.47960(8) 0.56314(16) 0.35708(14) 0.0361(4) Uani 1 1 d . . . H11A H 0.5067 0.6159 0.3603 0.043 Uiso 1 1 calc R . . C12 C 0.42309(8) 0.59904(14) 0.31708(13) 0.0304(4) Uani 1 1 d . . . H12A H 0.4109 0.6749 0.2924 0.037 Uiso 1 1 calc R . . C13 C 0.32306(7) 0.53083(13) 0.27612(11) 0.0243(3) Uani 1 1 d . . . C14 C 0.35226(7) 0.34611(13) 0.33821(11) 0.0250(3) Uani 1 1 d . . . C15 C 0.25973(7) 0.58422(13) 0.45108(12) 0.0260(4) Uani 1 1 d . . . C16 C 0.29762(8) 0.57123(14) 0.55968(12) 0.0287(4) Uani 1 1 d . . . H16A H 0.3030 0.6465 0.5907 0.043 Uiso 1 1 calc R . . H16B H 0.3352 0.5406 0.5781 0.043 Uiso 1 1 calc R . . H16C H 0.2795 0.5181 0.5816 0.043 Uiso 1 1 calc R . . C17 C 0.16306(7) 0.35852(14) 0.40008(12) 0.0287(4) Uani 1 1 d . . . C18 C 0.16686(9) 0.24214(16) 0.44269(15) 0.0404(5) Uani 1 1 d . . . H18A H 0.1773 0.2508 0.5101 0.061 Uiso 1 1 calc R . . H18B H 0.1964 0.1962 0.4424 0.061 Uiso 1 1 calc R . . H18C H 0.1294 0.2033 0.4034 0.061 Uiso 1 1 calc R . . C19 C 0.02632(7) 0.46897(14) 0.12146(13) 0.0291(4) Uani 1 1 d . . . C20 C -0.02731(8) 0.40695(16) 0.09698(14) 0.0346(4) Uani 1 1 d . . . H20A H -0.0571 0.4631 0.0841 0.052 Uiso 1 1 calc R . . H20B H -0.0187 0.3578 0.1522 0.052 Uiso 1 1 calc R . . H20C H -0.0413 0.3592 0.0386 0.052 Uiso 1 1 calc R . . C21 C 0.10735(7) 0.25938(14) -0.02987(12) 0.0273(4) Uani 1 1 d . . . C22 C 0.07606(8) 0.28151(16) -0.13774(13) 0.0366(4) Uani 1 1 d . . . H22A H 0.0680 0.2081 -0.1725 0.055 Uiso 1 1 calc R . . H22B H 0.1001 0.3295 -0.1508 0.055 Uiso 1 1 calc R . . H22C H 0.0396 0.3214 -0.1605 0.055 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 0.0309(6) 0.0194(5) 0.0249(6) -0.0021(4) 0.0160(5) 0.0007(4) O2 0.0403(7) 0.0206(6) 0.0333(6) -0.0013(5) 0.0198(6) 0.0038(5) O3 0.0331(6) 0.0198(5) 0.0294(6) 0.0014(4) 0.0200(5) 0.0004(4) O4 0.0488(8) 0.0302(7) 0.0395(7) -0.0033(5) 0.0314(7) -0.0012(5) O5 0.0257(6) 0.0216(6) 0.0352(6) 0.0003(5) 0.0169(5) 0.0007(4) O6 0.0383(8) 0.0245(7) 0.0731(10) 0.0010(6) 0.0338(8) 0.0038(5) O7 0.0300(6) 0.0236(6) 0.0241(6) -0.0011(4) 0.0129(5) 0.0009(4) O8 0.0361(7) 0.0237(6) 0.0327(6) -0.0029(5) 0.0178(6) 0.0001(5) O9 0.0302(6) 0.0208(6) 0.0341(6) 0.0026(5) 0.0176(6) 0.0021(5) O10 0.0368(7) 0.0227(6) 0.0410(7) 0.0064(5) 0.0238(6) 0.0043(5) N1 0.0264(7) 0.0191(7) 0.0271(7) -0.0006(5) 0.0155(6) 0.0008(5) C1 0.0280(9) 0.0188(8) 0.0268(8) 0.0001(6) 0.0164(7) 0.0001(6) C2 0.0288(9) 0.0189(8) 0.0227(8) 0.0003(6) 0.0147(7) 0.0012(6) C3 0.0314(9) 0.0173(8) 0.0290(8) 0.0003(6) 0.0187(8) 0.0013(6) C4 0.0272(9) 0.0199(8) 0.0293(8) 0.0012(6) 0.0165(8) 0.0009(6) C5 0.0272(9) 0.0212(8) 0.0223(8) -0.0003(6) 0.0122(7) 0.0002(6) C6 0.0291(9) 0.0209(8) 0.0253(8) -0.0016(6) 0.0159(7) 0.0001(6) C7 0.0296(9) 0.0234(8) 0.0267(8) -0.0030(6) 0.0162(8) -0.0001(6) C8 0.0319(9) 0.0241(8) 0.0276(8) -0.0021(6) 0.0175(8) 0.0005(6) C9 0.0334(10) 0.0263(9) 0.0384(10) 0.0021(7) 0.0195(9) 0.0047(7) C10 0.0276(10) 0.0344(10) 0.0467(11) -0.0010(8) 0.0198(9) 0.0027(7) C11 0.0328(10) 0.0301(9) 0.0488(11) -0.0032(8) 0.0247(9) -0.0039(7) C12 0.0349(10) 0.0220(8) 0.0377(9) -0.0009(7) 0.0221(9) -0.0004(7) C13 0.0296(9) 0.0195(8) 0.0248(8) -0.0033(6) 0.0156(8) -0.0020(6) C14 0.0299(9) 0.0224(8) 0.0239(8) -0.0002(6) 0.0155(7) 0.0028(6) C15 0.0313(9) 0.0203(8) 0.0311(9) -0.0035(6) 0.0203(8) -0.0025(6) C16 0.0362(10) 0.0234(8) 0.0296(9) -0.0024(7) 0.0203(8) 0.0001(7) C17 0.0310(9) 0.0275(9) 0.0310(9) 0.0002(7) 0.0192(8) -0.0002(7) C18 0.0565(13) 0.0313(10) 0.0413(11) 0.0054(8) 0.0320(10) -0.0001(8) C19 0.0293(9) 0.0265(9) 0.0320(9) 0.0040(7) 0.0173(8) 0.0053(7) C20 0.0317(10) 0.0324(10) 0.0417(10) 0.0051(8) 0.0216(9) 0.0038(7) C21 0.0239(9) 0.0290(9) 0.0291(9) -0.0055(7) 0.0148(8) -0.0044(7) C22 0.0392(11) 0.0375(10) 0.0274(9) -0.0033(7) 0.0149(9) -0.0006(8) _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 C15 1.3632(18) . ? O1 C2 1.4405(18) . ? O2 C15 1.199(2) . ? O3 C17 1.358(2) . ? O3 C3 1.4485(18) . ? O4 C17 1.202(2) . ? O5 C19 1.352(2) . ? O5 C4 1.4426(19) . ? O6 C19 1.201(2) . ? O7 C21 1.3474(19) . ? O7 C5 1.4464(18) . ? O8 C21 1.202(2) . ? O9 C13 1.2100(19) . ? O10 C14 1.2127(19) . ? N1 C13 1.403(2) . ? N1 C14 1.404(2) . ? N1 C1 1.463(2) . ? C1 C6 1.526(2) . ? C1 C2 1.529(2) . ? C1 H1A 1.0000 . ? C2 C3 1.528(2) . ? C2 H2A 1.0000 . ? C3 C4 1.525(2) . ? C3 H3A 1.0000 . ? C4 C5 1.513(2) . ? C4 H4A 1.0000 . ? C5 C6 1.518(2) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.385(2) . ? C7 C8 1.387(2) . ? C7 C13 1.483(2) . ? C8 C9 1.376(2) . ? C8 C14 1.494(2) . ? C9 C10 1.398(3) . ? C9 H9A 0.9500 . ? C10 C11 1.392(3) . ? C10 H10A 0.9500 . ? C11 C12 1.389(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C15 C16 1.492(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.497(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.496(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.499(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C15 O1 C2 115.44(12) . . ? C17 O3 C3 116.51(12) . . ? C19 O5 C4 117.97(12) . . ? C21 O7 C5 116.24(12) . . ? C13 N1 C14 111.50(13) . . ? C13 N1 C1 125.03(13) . . ? C14 N1 C1 123.37(13) . . ? N1 C1 C6 111.02(12) . . ? N1 C1 C2 111.08(13) . . ? C6 C1 C2 109.22(13) . . ? N1 C1 H1A 108.5 . . ? C6 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? O1 C2 C3 109.36(12) . . ? O1 C2 C1 106.59(12) . . ? C3 C2 C1 111.48(13) . . ? O1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O3 C3 C4 107.68(12) . . ? O3 C3 C2 109.06(12) . . ? C4 C3 C2 111.34(13) . . ? O3 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O5 C4 C5 106.58(12) . . ? O5 C4 C3 109.70(13) . . ? C5 C4 C3 111.71(13) . . ? O5 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? O7 C5 C4 106.48(12) . . ? O7 C5 C6 107.84(12) . . ? C4 C5 C6 111.37(13) . . ? O7 C5 H5A 110.4 . . ? C4 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? C5 C6 C1 110.93(13) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C12 C7 C8 121.63(16) . . ? C12 C7 C13 129.54(15) . . ? C8 C7 C13 108.83(14) . . ? C9 C8 C7 121.76(16) . . ? C9 C8 C14 130.58(15) . . ? C7 C8 C14 107.66(14) . . ? C8 C9 C10 117.14(16) . . ? C8 C9 H9A 121.4 . . ? C10 C9 H9A 121.4 . . ? C11 C10 C9 120.97(17) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C12 C11 C10 121.58(17) . . ? C12 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C7 C12 C11 116.92(16) . . ? C7 C12 H12A 121.5 . . ? C11 C12 H12A 121.5 . . ? O9 C13 N1 125.42(15) . . ? O9 C13 C7 128.64(15) . . ? N1 C13 C7 105.90(13) . . ? O10 C14 N1 124.92(15) . . ? O10 C14 C8 129.00(15) . . ? N1 C14 C8 106.08(13) . . ? O2 C15 O1 122.44(15) . . ? O2 C15 C16 127.30(15) . . ? O1 C15 C16 110.23(13) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 O3 123.82(15) . . ? O4 C17 C18 125.44(15) . . ? O3 C17 C18 110.74(14) . . ? 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 . . ? O6 C19 O5 122.94(16) . . ? O6 C19 C20 126.40(16) . . ? O5 C19 C20 110.67(14) . . ? 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 . . ? O8 C21 O7 123.42(15) . . ? O8 C21 C22 126.17(15) . . ? O7 C21 C22 110.41(14) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C13 N1 C1 C6 68.92(18) . . . . ? C14 N1 C1 C6 -106.99(16) . . . . ? C13 N1 C1 C2 -52.82(19) . . . . ? C14 N1 C1 C2 131.28(15) . . . . ? C15 O1 C2 C3 -80.37(15) . . . . ? C15 O1 C2 C1 158.99(12) . . . . ? N1 C1 C2 O1 -60.65(15) . . . . ? C6 C1 C2 O1 176.57(12) . . . . ? N1 C1 C2 C3 -179.92(12) . . . . ? C6 C1 C2 C3 57.30(16) . . . . ? C17 O3 C3 C4 -139.76(14) . . . . ? C17 O3 C3 C2 99.29(15) . . . . ? O1 C2 C3 O3 -53.87(15) . . . . ? C1 C2 C3 O3 63.74(16) . . . . ? O1 C2 C3 C4 -172.56(12) . . . . ? C1 C2 C3 C4 -54.95(17) . . . . ? C19 O5 C4 C5 -151.36(13) . . . . ? C19 O5 C4 C3 87.53(16) . . . . ? O3 C3 C4 O5 51.45(16) . . . . ? C2 C3 C4 O5 170.97(12) . . . . ? O3 C3 C4 C5 -66.50(16) . . . . ? C2 C3 C4 C5 53.01(17) . . . . ? C21 O7 C5 C4 -153.64(13) . . . . ? C21 O7 C5 C6 86.73(15) . . . . ? O5 C4 C5 O7 68.44(15) . . . . ? C3 C4 C5 O7 -171.75(12) . . . . ? O5 C4 C5 C6 -174.25(12) . . . . ? C3 C4 C5 C6 -54.44(17) . . . . ? O7 C5 C6 C1 174.08(12) . . . . ? C4 C5 C6 C1 57.60(17) . . . . ? N1 C1 C6 C5 178.75(12) . . . . ? C2 C1 C6 C5 -58.43(17) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? C13 C7 C8 C9 178.66(15) . . . . ? C12 C7 C8 C14 179.33(15) . . . . ? C13 C7 C8 C14 -1.45(18) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C14 C8 C9 C10 -179.12(17) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? C13 C7 C12 C11 -179.10(16) . . . . ? C10 C11 C12 C7 0.5(3) . . . . ? C14 N1 C13 O9 176.39(15) . . . . ? C1 N1 C13 O9 0.1(2) . . . . ? C14 N1 C13 C7 -1.47(17) . . . . ? C1 N1 C13 C7 -177.80(13) . . . . ? C12 C7 C13 O9 3.2(3) . . . . ? C8 C7 C13 O9 -175.96(16) . . . . ? C12 C7 C13 N1 -179.05(16) . . . . ? C8 C7 C13 N1 1.81(17) . . . . ? C13 N1 C14 O10 -179.73(15) . . . . ? C1 N1 C14 O10 -3.3(2) . . . . ? C13 N1 C14 C8 0.62(17) . . . . ? C1 N1 C14 C8 177.01(13) . . . . ? C9 C8 C14 O10 0.8(3) . . . . ? C7 C8 C14 O10 -179.08(16) . . . . ? C9 C8 C14 N1 -179.56(17) . . . . ? C7 C8 C14 N1 0.56(17) . . . . ? C2 O1 C15 O2 -2.2(2) . . . . ? C2 O1 C15 C16 176.30(13) . . . . ? C3 O3 C17 O4 2.7(2) . . . . ? C3 O3 C17 C18 -177.76(14) . . . . ? C4 O5 C19 O6 -0.9(2) . . . . ? C4 O5 C19 C20 179.55(14) . . . . ? C5 O7 C21 O8 9.2(2) . . . . ? C5 O7 C21 C22 -170.27(13) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.236 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.042 data_don1b _database_code_depnum_ccdc_archive 'CCDC 767844' #TrackingRef 'don1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 5.4050(3) _cell_length_b 7.6853(4) _cell_length_c 15.2798(8) _cell_angle_alpha 76.891(3) _cell_angle_beta 89.431(4) _cell_angle_gamma 78.624(3) _cell_volume 605.62(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2885 _cell_measurement_theta_min 3 _cell_measurement_theta_max 66 _exptl_crystal_description 'flat needles' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6843 _exptl_absorpt_correction_T_max 0.9619 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4840 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 67.23 _reflns_number_total 2009 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)' _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _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^)+(0.0586P)^2^+0.2863P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2009 _refine_ls_number_parameters 253 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.052 _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 0.5107(2) 0.22288(17) 0.63183(8) 0.0385(3) Uani 1 1 d . . . O2 O -0.1821(3) 0.28733(19) 0.80528(9) 0.0471(4) Uani 1 1 d . . . N1 N 0.1850(3) 0.21127(19) 0.73138(9) 0.0313(4) Uani 1 1 d . . . C1 C -0.0616(3) 0.4938(2) 0.67276(11) 0.0316(4) Uani 1 1 d . . . C2 C -0.2520(4) 0.6484(3) 0.65240(13) 0.0397(4) Uani 1 1 d . A . H2A H -0.3978 0.6607 0.6875 0.048 Uiso 1 1 calc R . . C3 C -0.2203(4) 0.7846(2) 0.57831(14) 0.0431(5) Uani 1 1 d . . . H3A H -0.3466 0.8926 0.5627 0.052 Uiso 1 1 calc R A . C4 C -0.0086(4) 0.7661(2) 0.52688(13) 0.0394(5) Uani 1 1 d . A . H4A H 0.0062 0.8607 0.4761 0.047 Uiso 1 1 calc R . . C5 C 0.1822(4) 0.6118(2) 0.54811(12) 0.0350(4) Uani 1 1 d . . . H5A H 0.3289 0.5997 0.5134 0.042 Uiso 1 1 calc R A . C6 C 0.1506(3) 0.4763(2) 0.62183(11) 0.0299(4) Uani 1 1 d . A . C7 C -0.0406(3) 0.3250(2) 0.74532(11) 0.0335(4) Uani 1 1 d . A . C8 C 0.3117(3) 0.2936(2) 0.65838(11) 0.0298(4) Uani 1 1 d . A . O3 O 0.5239(3) -0.1226(3) 0.92861(11) 0.0433(6) Uani 0.762(3) 1 d PDU A 1 O4 O 0.2464(8) -0.4377(4) 0.99465(18) 0.0728(9) Uani 0.762(3) 1 d PDU A 1 H4 H 0.3650 -0.4939 0.9696 0.109 Uiso 0.762(3) 1 calc PR A 1 O5 O 0.3962(5) -0.3689(3) 0.81597(16) 0.0686(8) Uani 0.762(3) 1 d PDU A 1 H5 H 0.4460 -0.4675 0.8539 0.103 Uiso 0.762(3) 1 calc PR A 1 C11 C 0.2750(3) 0.0249(2) 0.78371(11) 0.0347(4) Uani 0.762(3) 1 d PDU A 1 H11A H 0.4393 -0.0251 0.7593 0.042 Uiso 0.762(3) 1 calc PR A 1 C12 C 0.3226(11) 0.0253(7) 0.8829(3) 0.0346(11) Uani 0.762(3) 1 d PDU A 1 H12A H 0.3154 0.1471 0.8970 0.042 Uiso 0.762(3) 1 calc PR A 1 C13 C 0.2673(5) -0.1191(4) 0.95610(16) 0.0328(6) Uani 0.762(3) 1 d PDU A 1 H13A H 0.2264 -0.0847 1.0147 0.039 Uiso 0.762(3) 1 calc PR A 1 C14 C 0.1435(12) -0.2656(8) 0.9360(4) 0.0427(7) Uani 0.762(3) 1 d PDU A 1 H14A H -0.0392 -0.2341 0.9494 0.051 Uiso 0.762(3) 1 calc PR A 1 C15 C 0.1560(7) -0.2832(4) 0.8390(2) 0.0406(7) Uani 0.762(3) 1 d PDU A 1 H15A H 0.0300 -0.3566 0.8287 0.049 Uiso 0.762(3) 1 calc PR A 1 C16 C 0.0896(15) -0.0977(8) 0.7751(4) 0.0401(15) Uani 0.762(3) 1 d PDU A 1 H16A H -0.0823 -0.0370 0.7872 0.048 Uiso 0.762(3) 1 calc PR A 1 H16B H 0.0876 -0.1136 0.7127 0.048 Uiso 0.762(3) 1 calc PR A 1 O3A O 0.1992(12) -0.2822(9) 0.7690(5) 0.059(2) Uani 0.238(3) 1 d PDU A 2 O4A O 0.140(2) -0.4278(19) 0.9755(11) 0.144(8) Uani 0.238(3) 1 d PDU A 2 H4A1 H -0.0063 -0.4506 0.9796 0.216 Uiso 0.238(3) 1 calc PR A 2 O5A O 0.5806(14) -0.3030(14) 0.8941(6) 0.086(3) Uani 0.238(3) 1 d PDU A 2 H5A1 H 0.5355 -0.3140 0.8435 0.130 Uiso 0.238(3) 1 calc PR A 2 C11A C 0.2750(3) 0.0249(2) 0.78371(11) 0.0347(4) Uani 0.238(3) 1 d PDU A 2 H11B H 0.4366 -0.0197 0.7560 0.042 Uiso 0.238(3) 1 calc PR A 2 C12A C 0.089(4) -0.091(2) 0.7615(14) 0.040(4) Uani 0.238(3) 1 d PDU A 2 H12B H -0.0414 -0.0313 0.7122 0.048 Uiso 0.238(3) 1 calc PR A 2 C13A C 0.023(2) -0.2297(14) 0.8336(6) 0.041(2) Uani 0.238(3) 1 d PDU A 2 H13B H -0.1489 -0.2569 0.8291 0.050 Uiso 0.238(3) 1 calc PR A 2 C14A C 0.127(4) -0.248(3) 0.9269(13) 0.0427(7) Uani 0.238(3) 1 d PDU A 2 H14B H 0.0025 -0.1676 0.9565 0.051 Uiso 0.238(3) 1 calc PR A 2 C15A C 0.378(2) -0.1885(14) 0.9291(6) 0.054(2) Uani 0.238(3) 1 d PDU A 2 H15B H 0.4239 -0.1940 0.9931 0.065 Uiso 0.238(3) 1 calc PR A 2 C16A C 0.343(4) 0.010(2) 0.8768(12) 0.053(5) Uani 0.238(3) 1 d PDU A 2 H16C H 0.2090 0.0863 0.9038 0.064 Uiso 0.238(3) 1 calc PR A 2 H16D H 0.5019 0.0539 0.8804 0.064 Uiso 0.238(3) 1 calc PR A 2 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 0.0366(7) 0.0379(7) 0.0378(7) -0.0042(5) 0.0087(5) -0.0056(5) O2 0.0455(8) 0.0514(8) 0.0424(8) -0.0053(6) 0.0170(6) -0.0118(6) N1 0.0326(8) 0.0311(8) 0.0290(7) -0.0029(6) 0.0030(6) -0.0081(6) C1 0.0342(10) 0.0314(9) 0.0333(9) -0.0119(7) -0.0002(7) -0.0107(7) C2 0.0361(11) 0.0377(10) 0.0482(11) -0.0168(8) 0.0008(8) -0.0061(8) C3 0.0495(12) 0.0271(9) 0.0521(11) -0.0114(8) -0.0125(9) -0.0028(8) C4 0.0534(12) 0.0279(9) 0.0386(10) -0.0057(7) -0.0072(8) -0.0144(8) C5 0.0433(11) 0.0316(9) 0.0332(9) -0.0083(7) 0.0006(7) -0.0135(7) C6 0.0334(9) 0.0301(9) 0.0292(8) -0.0092(7) -0.0011(6) -0.0108(7) C7 0.0333(10) 0.0374(10) 0.0322(9) -0.0104(7) 0.0035(7) -0.0102(7) C8 0.0322(10) 0.0321(9) 0.0272(8) -0.0072(7) 0.0018(6) -0.0105(7) O3 0.0278(11) 0.0539(12) 0.0389(10) 0.0075(8) -0.0055(7) -0.0068(8) O4 0.116(3) 0.0435(13) 0.0494(14) 0.0160(11) -0.0024(16) -0.0232(16) O5 0.0863(18) 0.0402(12) 0.0663(14) -0.0077(10) 0.0261(13) 0.0112(11) C11 0.0334(10) 0.0330(9) 0.0343(9) -0.0008(7) 0.0016(7) -0.0068(7) C12 0.033(2) 0.0360(18) 0.0309(19) -0.0006(16) -0.0088(16) -0.0046(15) C13 0.0302(14) 0.0377(14) 0.0273(12) -0.0022(10) 0.0011(9) -0.0051(10) C14 0.0472(15) 0.0394(16) 0.0388(16) 0.0038(11) 0.0061(11) -0.0175(12) C15 0.053(2) 0.0277(16) 0.0403(16) -0.0045(11) 0.0040(14) -0.0090(14) C16 0.054(4) 0.033(2) 0.034(2) -0.0068(16) -0.007(2) -0.0116(19) O3A 0.048(4) 0.060(4) 0.079(5) -0.031(4) 0.030(4) -0.022(3) O4A 0.096(9) 0.113(8) 0.176(12) 0.111(9) -0.100(9) -0.072(7) O5A 0.040(4) 0.124(7) 0.093(6) -0.034(6) -0.004(4) -0.002(4) C11A 0.0334(10) 0.0330(9) 0.0343(9) -0.0008(7) 0.0016(7) -0.0068(7) C12A 0.039(10) 0.045(7) 0.039(7) -0.008(5) 0.012(6) -0.017(6) C13A 0.040(6) 0.036(5) 0.051(5) -0.011(4) 0.005(4) -0.012(4) C14A 0.0472(15) 0.0394(16) 0.0388(16) 0.0038(11) 0.0061(11) -0.0175(12) C15A 0.055(7) 0.061(6) 0.042(5) 0.004(4) -0.007(4) -0.019(5) C16A 0.054(11) 0.066(7) 0.052(8) -0.005(8) 0.016(7) -0.052(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.215(2) . ? O2 C7 1.209(2) . ? N1 C8 1.396(2) . ? N1 C7 1.399(2) . ? N1 C11 1.463(2) . ? C1 C6 1.381(2) . ? C1 C2 1.387(3) . ? C1 C7 1.489(2) . ? C2 C3 1.391(3) . ? C2 H2A 0.9500 . ? C3 C4 1.384(3) . ? C3 H3A 0.9500 . ? C4 C5 1.387(3) . ? C4 H4A 0.9500 . ? C5 C6 1.384(2) . ? C5 H5A 0.9500 . ? C6 C8 1.488(2) . ? O3 C13 1.442(3) . ? O3 C12 1.460(4) . ? O4 C14 1.429(5) . ? O4 H4 0.8400 . ? O5 C15 1.415(4) . ? O5 H5 0.8400 . ? C11 C16 1.530(6) . ? C11 C12 1.541(5) . ? C11 H11A 1.0000 . ? C12 C13 1.460(6) . ? C12 H12A 1.0000 . ? C13 C14 1.506(8) . ? C13 H13A 1.0000 . ? C14 C15 1.519(8) . ? C14 H14A 1.0000 . ? C15 C16 1.513(6) . ? C15 H15A 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O3A C13A 1.432(10) . ? O3A C12A 1.451(19) . ? O4A C14A 1.400(15) . ? O4A H4A1 0.8400 . ? O5A C15A 1.442(12) . ? O5A H5A1 0.8400 . ? C12A C13A 1.443(17) . ? C12A H12B 1.0000 . ? C13A C14A 1.50(2) . ? C13A H13B 1.0000 . ? C14A C15A 1.520(19) . ? C14A H14B 1.0000 . ? C15A C16A 1.526(16) . ? C15A H15B 1.0000 . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 111.95(14) . . ? C8 N1 C11 123.26(14) . . ? C7 N1 C11 124.73(14) . . ? C6 C1 C2 121.38(17) . . ? C6 C1 C7 108.39(15) . . ? C2 C1 C7 130.22(17) . . ? C1 C2 C3 117.07(18) . . ? C1 C2 H2A 121.5 . . ? C3 C2 H2A 121.5 . . ? C4 C3 C2 121.46(17) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 121.16(17) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C6 C5 C4 117.37(18) . . ? C6 C5 H5A 121.3 . . ? C4 C5 H5A 121.3 . . ? C1 C6 C5 121.54(16) . . ? C1 C6 C8 108.21(15) . . ? C5 C6 C8 130.19(16) . . ? O2 C7 N1 124.90(17) . . ? O2 C7 C1 129.50(17) . . ? N1 C7 C1 105.61(14) . . ? O1 C8 N1 124.91(16) . . ? O1 C8 C6 129.26(16) . . ? N1 C8 C6 105.82(14) . . ? C13 O3 C12 60.4(3) . . ? N1 C11 C16 111.3(3) . . ? N1 C11 C12 110.2(2) . . ? C16 C11 C12 111.1(3) . . ? N1 C11 H11A 108.1 . . ? C16 C11 H11A 108.1 . . ? C12 C11 H11A 108.1 . . ? O3 C12 C13 59.2(2) . . ? O3 C12 C11 113.7(4) . . ? C13 C12 C11 121.5(4) . . ? O3 C12 H12A 116.5 . . ? C13 C12 H12A 116.5 . . ? C11 C12 H12A 116.5 . . ? O3 C13 C12 60.4(2) . . ? O3 C13 C14 116.4(3) . . ? C12 C13 C14 120.2(3) . . ? O3 C13 H13A 116.1 . . ? C12 C13 H13A 116.1 . . ? C14 C13 H13A 116.1 . . ? O4 C14 C13 110.3(5) . . ? O4 C14 C15 109.8(5) . . ? C13 C14 C15 114.9(3) . . ? O4 C14 H14A 107.2 . . ? C13 C14 H14A 107.2 . . ? C15 C14 H14A 107.2 . . ? O5 C15 C16 107.1(4) . . ? O5 C15 C14 113.8(3) . . ? C16 C15 C14 110.7(4) . . ? O5 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C15 C16 C11 112.8(4) . . ? C15 C16 H16A 109.0 . . ? C11 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C11 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C13A O3A C12A 60.1(8) . . ? C14A O4A H4A1 109.5 . . ? C15A O5A H5A1 109.5 . . ? C13A C12A O3A 59.3(8) . . ? C13A C12A H12B 117.3 . . ? O3A C12A H12B 117.3 . . ? O3A C13A C12A 60.6(9) . . ? O3A C13A C14A 117.0(11) . . ? C12A C13A C14A 118.6(12) . . ? O3A C13A H13B 116.3 . . ? C12A C13A H13B 116.3 . . ? C14A C13A H13B 116.3 . . ? O4A C14A C13A 108.7(17) . . ? O4A C14A C15A 112.2(14) . . ? C13A C14A C15A 113.8(11) . . ? O4A C14A H14B 107.3 . . ? C13A C14A H14B 107.3 . . ? C15A C14A H14B 107.3 . . ? O5A C15A C14A 113.0(12) . . ? O5A C15A C16A 111.1(12) . . ? C14A C15A C16A 108.2(11) . . ? O5A C15A H15B 108.2 . . ? C14A C15A H15B 108.2 . . ? C16A C15A H15B 108.2 . . ? C15A C16A H16C 109.6 . . ? C15A C16A H16D 109.6 . . ? H16C C16A H16D 108.1 . . ? 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 C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 -178.75(16) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C7 C1 C6 C5 178.94(15) . . . . ? C2 C1 C6 C8 -177.59(15) . . . . ? C7 C1 C6 C8 1.56(18) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C4 C5 C6 C8 176.38(16) . . . . ? C8 N1 C7 O2 -178.34(17) . . . . ? C11 N1 C7 O2 4.3(3) . . . . ? C8 N1 C7 C1 1.46(18) . . . . ? C11 N1 C7 C1 -175.93(14) . . . . ? C6 C1 C7 O2 177.92(18) . . . . ? C2 C1 C7 O2 -3.0(3) . . . . ? C6 C1 C7 N1 -1.87(18) . . . . ? C2 C1 C7 N1 177.19(17) . . . . ? C7 N1 C8 O1 -179.34(16) . . . . ? C11 N1 C8 O1 -1.9(3) . . . . ? C7 N1 C8 C6 -0.55(18) . . . . ? C11 N1 C8 C6 176.89(14) . . . . ? C1 C6 C8 O1 178.04(17) . . . . ? C5 C6 C8 O1 1.0(3) . . . . ? C1 C6 C8 N1 -0.68(17) . . . . ? C5 C6 C8 N1 -177.76(17) . . . . ? C8 N1 C11 C16 -116.1(4) . . . . ? C7 N1 C11 C16 61.0(4) . . . . ? C8 N1 C11 C12 120.2(3) . . . . ? C7 N1 C11 C12 -62.7(3) . . . . ? C13 O3 C12 C11 -113.7(4) . . . . ? N1 C11 C12 O3 -149.5(3) . . . . ? C16 C11 C12 O3 86.7(5) . . . . ? N1 C11 C12 C13 143.3(4) . . . . ? C16 C11 C12 C13 19.4(5) . . . . ? C12 O3 C13 C14 111.3(4) . . . . ? C11 C12 C13 O3 100.6(5) . . . . ? O3 C12 C13 C14 -105.2(4) . . . . ? C11 C12 C13 C14 -4.6(6) . . . . ? O3 C13 C14 O4 72.7(5) . . . . ? C12 C13 C14 O4 142.3(4) . . . . ? O3 C13 C14 C15 -52.1(5) . . . . ? C12 C13 C14 C15 17.5(6) . . . . ? O4 C14 C15 O5 -49.8(5) . . . . ? C13 C14 C15 O5 75.3(5) . . . . ? O4 C14 C15 C16 -170.5(5) . . . . ? C13 C14 C15 C16 -45.4(6) . . . . ? O5 C15 C16 C11 -62.0(6) . . . . ? C14 C15 C16 C11 62.6(7) . . . . ? N1 C11 C16 C15 -171.4(4) . . . . ? C12 C11 C16 C15 -48.2(6) . . . . ? C12A O3A C13A C14A -109.2(14) . . . . ? O3A C12A C13A C14A 106.7(15) . . . . ? O3A C13A C14A O4A -84.4(15) . . . . ? C12A C13A C14A O4A -154.0(16) . . . . ? O3A C13A C14A C15A 41.4(19) . . . . ? C12A C13A C14A C15A -28(2) . . . . ? O4A C14A C15A O5A 58(2) . . . . ? C13A C14A C15A O5A -65.8(16) . . . . ? O4A C14A C15A C16A -178.4(17) . . . . ? C13A C14A C15A C16A 58(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.84 2.11 2.714(8) 128.7 2_647 O4 H4 O5 0.84 2.34 2.804(4) 115.0 . O5 H5 O4 0.84 2.74 3.368(4) 133.2 2_647 O4A H4A1 O4A 0.84 1.35 2.08(2) 142.4 2_547 O5A H5A1 O3A 0.84 2.10 2.781(11) 138.3 . _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 67.23 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.304 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.037 data_donz _database_code_depnum_ccdc_archive 'CCDC 767845' #TrackingRef 'CCDC 767845 revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.52500(10) _cell_length_b 17.7359(2) _cell_length_c 12.5209(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.8490(10) _cell_angle_gamma 90.00 _cell_volume 1225.42(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6135 _cell_measurement_theta_min 4 _cell_measurement_theta_max 67 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8228 _exptl_absorpt_correction_T_max 0.9354 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10319 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 68.17 _reflns_number_total 2194 _reflns_number_gt 2047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _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^)+(0.0515P)^2^+0.6172P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2194 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.21394(16) 0.62234(5) 0.03746(7) 0.0193(2) Uani 1 1 d . . . O2 O 0.82476(17) 0.67566(5) -0.18510(8) 0.0211(2) Uani 1 1 d . . . O3 O 0.25889(17) 0.79920(5) -0.12981(8) 0.0211(2) Uani 1 1 d . . . O4 O 0.44690(17) 0.89069(5) 0.06404(8) 0.0223(2) Uani 1 1 d . . . O5 O 0.74681(18) 0.81379(5) 0.21296(7) 0.0204(2) Uani 1 1 d . . . N1 N 0.53436(19) 0.66624(6) -0.05849(8) 0.0155(2) Uani 1 1 d . . . C1 C 0.3764(2) 0.54992(7) -0.10806(10) 0.0161(3) Uani 1 1 d . . . C2 C 0.2375(2) 0.48539(8) -0.12090(10) 0.0187(3) Uani 1 1 d . . . C3 C 0.2997(3) 0.43571(8) -0.20165(11) 0.0201(3) Uani 1 1 d . . . C4 C 0.4935(3) 0.45025(8) -0.26555(11) 0.0205(3) Uani 1 1 d . . . C5 C 0.6314(2) 0.51573(7) -0.25231(10) 0.0186(3) Uani 1 1 d . . . C6 C 0.5671(2) 0.56497(7) -0.17268(10) 0.0166(3) Uani 1 1 d . . . C7 C 0.3543(2) 0.61433(7) -0.03257(10) 0.0151(3) Uani 1 1 d . . . C8 C 0.6657(2) 0.64067(7) -0.14356(10) 0.0161(3) Uani 1 1 d . . . C9 C 0.5622(2) 0.74057(7) -0.00757(10) 0.0153(3) Uani 1 1 d . . . C10 C 0.5027(2) 0.80295(7) -0.08979(10) 0.0164(3) Uani 1 1 d . . . C11 C 0.5422(2) 0.87964(7) -0.04018(11) 0.0187(3) Uani 1 1 d . . . C12 C 0.7074(2) 0.89054(8) 0.05397(11) 0.0199(3) Uani 1 1 d . . . C13 C 0.8361(2) 0.82420(8) 0.10849(10) 0.0184(3) Uani 1 1 d . . . C14 C 0.8172(2) 0.75236(7) 0.04231(10) 0.0176(3) Uani 1 1 d . . . H3O H 0.249(4) 0.7634(12) -0.1793(17) 0.041(5) Uiso 1 1 d . . . H5O H 0.593(4) 0.8258(10) 0.2130(14) 0.032(5) Uiso 1 1 d . . . H2 H 0.104(3) 0.4754(9) -0.0770(12) 0.017(4) Uiso 1 1 d . . . H3 H 0.207(3) 0.3911(9) -0.2153(12) 0.020(4) Uiso 1 1 d . . . H4 H 0.527(3) 0.4126(9) -0.3196(13) 0.022(4) Uiso 1 1 d . . . H5 H 0.762(3) 0.5269(8) -0.2964(12) 0.016(4) Uiso 1 1 d . . . H9 H 0.446(2) 0.7404(8) 0.0460(11) 0.006(3) Uiso 1 1 d . . . H10 H 0.615(3) 0.7983(8) -0.1480(12) 0.012(3) Uiso 1 1 d . . . H11 H 0.510(3) 0.9217(9) -0.0902(12) 0.019(4) Uiso 1 1 d . . . H12 H 0.783(3) 0.9382(9) 0.0653(12) 0.015(4) Uiso 1 1 d . . . H13 H 1.007(3) 0.8381(8) 0.1177(12) 0.014(3) Uiso 1 1 d . . . H14A H 0.930(3) 0.7556(8) -0.0132(12) 0.015(4) Uiso 1 1 d . . . H14B H 0.870(3) 0.7115(9) 0.0929(12) 0.017(4) 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 0.0185(5) 0.0191(5) 0.0206(5) 0.0004(4) 0.0056(4) 0.0003(4) O2 0.0213(5) 0.0209(5) 0.0218(5) -0.0029(4) 0.0075(4) -0.0047(4) O3 0.0215(5) 0.0186(5) 0.0228(5) -0.0003(4) -0.0038(4) 0.0003(4) O4 0.0238(5) 0.0228(5) 0.0204(5) -0.0020(4) 0.0014(4) 0.0033(4) O5 0.0184(5) 0.0263(5) 0.0167(5) -0.0002(4) 0.0019(4) 0.0015(4) N1 0.0166(5) 0.0143(5) 0.0158(5) 0.0001(4) 0.0027(4) 0.0000(4) C1 0.0166(6) 0.0161(6) 0.0155(6) 0.0022(5) -0.0008(5) 0.0022(5) C2 0.0192(6) 0.0185(7) 0.0182(6) 0.0028(5) 0.0001(5) -0.0009(5) C3 0.0247(7) 0.0151(6) 0.0201(7) 0.0013(5) -0.0030(5) -0.0027(5) C4 0.0262(7) 0.0176(7) 0.0176(6) -0.0015(5) -0.0002(5) 0.0030(5) C5 0.0202(7) 0.0188(7) 0.0170(6) 0.0010(5) 0.0022(5) 0.0027(5) C6 0.0171(6) 0.0164(6) 0.0160(6) 0.0021(5) -0.0010(5) 0.0019(5) C7 0.0136(6) 0.0155(6) 0.0160(6) 0.0036(5) -0.0009(5) 0.0020(5) C8 0.0154(6) 0.0177(6) 0.0152(6) 0.0004(5) 0.0005(5) 0.0018(5) C9 0.0167(6) 0.0144(6) 0.0149(6) -0.0012(5) 0.0038(5) 0.0003(5) C10 0.0169(6) 0.0164(7) 0.0160(6) 0.0003(5) 0.0012(5) -0.0015(5) C11 0.0217(7) 0.0164(6) 0.0184(7) 0.0013(5) 0.0037(5) -0.0007(5) C12 0.0215(7) 0.0167(7) 0.0217(7) -0.0036(5) 0.0030(5) -0.0034(5) C13 0.0158(6) 0.0217(7) 0.0179(7) -0.0015(5) 0.0016(5) -0.0020(5) C14 0.0165(6) 0.0194(7) 0.0170(6) -0.0003(5) 0.0009(5) 0.0019(5) _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 C7 1.2075(16) . ? O2 C8 1.2137(16) . ? O3 C10 1.4153(16) . ? O3 H3O 0.89(2) . ? O4 C11 1.4446(16) . ? O4 C12 1.4512(16) . ? O5 C13 1.4327(16) . ? O5 H5O 0.88(2) . ? N1 C8 1.3942(16) . ? N1 C7 1.4052(16) . ? N1 C9 1.4693(16) . ? C1 C2 1.3832(19) . ? C1 C6 1.3856(18) . ? C1 C7 1.4916(18) . ? C2 C3 1.3970(19) . ? C2 H2 0.959(16) . ? C3 C4 1.392(2) . ? C3 H3 0.954(17) . ? C4 C5 1.394(2) . ? C4 H4 0.975(17) . ? C5 C6 1.3850(19) . ? C5 H5 0.951(16) . ? C6 C8 1.4876(18) . ? C9 C14 1.5266(18) . ? C9 C10 1.5357(18) . ? C9 H9 0.949(14) . ? C10 C11 1.5065(18) . ? C10 H10 0.986(15) . ? C11 C12 1.4675(19) . ? C11 H11 0.984(16) . ? C12 C13 1.5189(19) . ? C12 H12 0.951(16) . ? C13 C14 1.5208(18) . ? C13 H13 0.975(16) . ? C14 H14A 0.959(16) . ? C14 H14B 0.997(16) . ? 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 C10 O3 H3O 107.7(13) . . ? C11 O4 C12 60.90(8) . . ? C13 O5 H5O 110.3(12) . . ? C8 N1 C7 111.39(11) . . ? C8 N1 C9 125.17(10) . . ? C7 N1 C9 123.22(10) . . ? C2 C1 C6 121.68(12) . . ? C2 C1 C7 130.16(12) . . ? C6 C1 C7 108.13(11) . . ? C1 C2 C3 116.79(12) . . ? C1 C2 H2 121.7(9) . . ? C3 C2 H2 121.5(9) . . ? C4 C3 C2 121.55(13) . . ? C4 C3 H3 118.3(9) . . ? C2 C3 H3 120.2(9) . . ? C3 C4 C5 121.16(12) . . ? C3 C4 H4 116.8(9) . . ? C5 C4 H4 122.1(9) . . ? C6 C5 C4 116.90(12) . . ? C6 C5 H5 121.1(9) . . ? C4 C5 H5 122.0(9) . . ? C5 C6 C1 121.91(12) . . ? C5 C6 C8 129.91(12) . . ? C1 C6 C8 108.09(11) . . ? O1 C7 N1 125.32(12) . . ? O1 C7 C1 128.76(12) . . ? N1 C7 C1 105.91(10) . . ? O2 C8 N1 125.21(12) . . ? O2 C8 C6 128.36(12) . . ? N1 C8 C6 106.41(10) . . ? N1 C9 C14 112.03(10) . . ? N1 C9 C10 109.95(10) . . ? C14 C9 C10 109.76(10) . . ? N1 C9 H9 104.1(8) . . ? C14 C9 H9 110.6(8) . . ? C10 C9 H9 110.3(8) . . ? O3 C10 C11 107.72(11) . . ? O3 C10 C9 111.83(10) . . ? C11 C10 C9 110.62(11) . . ? O3 C10 H10 111.0(9) . . ? C11 C10 H10 107.3(8) . . ? C9 C10 H10 108.2(9) . . ? O4 C11 C12 59.77(8) . . ? O4 C11 C10 116.30(11) . . ? C12 C11 C10 121.45(12) . . ? O4 C11 H11 114.2(9) . . ? C12 C11 H11 119.8(9) . . ? C10 C11 H11 113.8(9) . . ? O4 C12 C11 59.33(8) . . ? O4 C12 C13 113.98(11) . . ? C11 C12 C13 121.16(12) . . ? O4 C12 H12 114.6(9) . . ? C11 C12 H12 119.2(9) . . ? C13 C12 H12 115.4(9) . . ? O5 C13 C12 109.61(10) . . ? O5 C13 C14 111.85(11) . . ? C12 C13 C14 112.72(11) . . ? O5 C13 H13 107.4(9) . . ? C12 C13 H13 106.6(9) . . ? C14 C13 H13 108.5(9) . . ? C13 C14 C9 112.00(10) . . ? C13 C14 H14A 108.4(9) . . ? C9 C14 H14A 109.4(9) . . ? C13 C14 H14B 104.7(9) . . ? C9 C14 H14B 113.3(9) . . ? H14A C14 H14B 108.9(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.51(19) . . . . ? C7 C1 C2 C3 178.18(12) . . . . ? C1 C2 C3 C4 0.46(19) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 0.29(19) . . . . ? C4 C5 C6 C1 0.68(19) . . . . ? C4 C5 C6 C8 -175.51(12) . . . . ? C2 C1 C6 C5 -1.12(19) . . . . ? C7 C1 C6 C5 -179.24(11) . . . . ? C2 C1 C6 C8 175.81(11) . . . . ? C7 C1 C6 C8 -2.31(14) . . . . ? C8 N1 C7 O1 -179.66(12) . . . . ? C9 N1 C7 O1 -4.75(19) . . . . ? C8 N1 C7 C1 0.46(13) . . . . ? C9 N1 C7 C1 175.37(10) . . . . ? C2 C1 C7 O1 3.4(2) . . . . ? C6 C1 C7 O1 -178.66(13) . . . . ? C2 C1 C7 N1 -176.70(13) . . . . ? C6 C1 C7 N1 1.21(13) . . . . ? C7 N1 C8 O2 176.76(12) . . . . ? C9 N1 C8 O2 2.0(2) . . . . ? C7 N1 C8 C6 -1.84(14) . . . . ? C9 N1 C8 C6 -176.63(11) . . . . ? C5 C6 C8 O2 0.6(2) . . . . ? C1 C6 C8 O2 -175.96(13) . . . . ? C5 C6 C8 N1 179.18(13) . . . . ? C1 C6 C8 N1 2.58(14) . . . . ? C8 N1 C9 C14 -61.31(15) . . . . ? C7 N1 C9 C14 124.49(12) . . . . ? C8 N1 C9 C10 61.03(15) . . . . ? C7 N1 C9 C10 -113.17(13) . . . . ? N1 C9 C10 O3 62.70(13) . . . . ? C14 C9 C10 O3 -173.63(10) . . . . ? N1 C9 C10 C11 -177.24(10) . . . . ? C14 C9 C10 C11 -53.56(14) . . . . ? C12 O4 C11 C10 112.68(13) . . . . ? O3 C10 C11 O4 77.02(13) . . . . ? C9 C10 C11 O4 -45.48(15) . . . . ? O3 C10 C11 C12 146.17(12) . . . . ? C9 C10 C11 C12 23.67(17) . . . . ? C11 O4 C12 C13 -113.25(13) . . . . ? C10 C11 C12 O4 -104.17(13) . . . . ? O4 C11 C12 C13 101.15(13) . . . . ? C10 C11 C12 C13 -3.02(19) . . . . ? O4 C12 C13 O5 -45.49(14) . . . . ? C11 C12 C13 O5 -112.94(13) . . . . ? O4 C12 C13 C14 79.78(14) . . . . ? C11 C12 C13 C14 12.33(17) . . . . ? O5 C13 C14 C9 80.91(13) . . . . ? C12 C13 C14 C9 -43.14(15) . . . . ? N1 C9 C14 C13 -171.80(10) . . . . ? C10 C9 C14 C13 65.75(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O O5 0.89(2) 1.92(2) 2.8076(14) 177.0(19) 4_575 O5 H5O O2 0.88(2) 2.003(19) 2.7198(13) 138.2(16) 4_576 O5 H5O O4 0.88(2) 2.304(19) 2.7885(13) 114.9(14) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 68.17 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.266 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.041 data_donw _database_code_depnum_ccdc_archive 'CCDC 767846' #TrackingRef 'CCDC 767846 revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O6' _chemical_formula_weight 343.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.4527(2) _cell_length_b 8.9213(2) _cell_length_c 21.1061(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.6100(10) _cell_angle_gamma 90.00 _cell_volume 1590.96(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8641 _cell_measurement_theta_min 4 _cell_measurement_theta_max 67 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6436 _exptl_absorpt_correction_T_max 0.9389 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13190 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 67.86 _reflns_number_total 2766 _reflns_number_gt 2659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2008.5-0 (Bruker, 2008)' _computing_cell_refinement 'SAINT v7.56A (Bruker, 2008)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _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^)+(0.0412P)^2^+0.7722P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2766 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.37585(10) 0.74248(10) 0.22470(4) 0.0212(2) Uani 1 1 d . . . O2 O 0.18195(10) 0.82807(9) 0.28634(4) 0.0177(2) Uani 1 1 d . . . O3 O -0.08011(12) 0.75815(10) 0.40064(4) 0.0275(2) Uani 1 1 d . . . O4 O -0.12208(10) 0.88694(9) 0.30962(4) 0.0169(2) Uani 1 1 d . . . O5 O -0.25236(10) 0.65748(10) 0.07464(4) 0.0238(2) Uani 1 1 d . . . O6 O -0.52227(11) 1.04825(10) 0.16250(4) 0.0225(2) Uani 1 1 d . . . N1 N -0.35631(12) 0.85707(11) 0.13059(5) 0.0171(2) Uani 1 1 d . . . C1 C -0.07877(15) 0.91651(14) 0.15750(6) 0.0193(3) Uani 1 1 d . . . H1A H -0.0756 0.9796 0.1213 0.023 Uiso 1 1 calc R . . C2 C 0.05661(15) 0.87083(13) 0.18390(6) 0.0184(3) Uani 1 1 d . . . H2A H 0.1524 0.9046 0.1663 0.022 Uiso 1 1 calc R . . C3 C 0.06665(14) 0.76836(13) 0.24030(6) 0.0165(3) Uani 1 1 d . . . H3A H 0.1024 0.6671 0.2263 0.020 Uiso 1 1 calc R . . C4 C -0.09047(14) 0.75246(13) 0.27318(6) 0.0165(3) Uani 1 1 d . . . H4A H -0.0865 0.6635 0.3020 0.020 Uiso 1 1 calc R . . C5 C -0.22333(14) 0.73271(13) 0.22382(6) 0.0170(3) Uani 1 1 d . . . H5A H -0.3244 0.7152 0.2452 0.020 Uiso 1 1 calc R . . H5B H -0.2014 0.6443 0.1971 0.020 Uiso 1 1 calc R . . C6 C -0.23744(14) 0.87305(13) 0.18217(6) 0.0175(3) Uani 1 1 d . . . H6A H -0.2730 0.9568 0.2099 0.021 Uiso 1 1 calc R . . C7 C 0.33565(14) 0.81267(13) 0.27042(6) 0.0173(3) Uani 1 1 d . . . C8 C 0.44505(14) 0.89493(14) 0.31550(6) 0.0200(3) Uani 1 1 d . . . H8A H 0.5206 0.8241 0.3350 0.030 Uiso 1 1 calc R . . H8B H 0.3834 0.9425 0.3486 0.030 Uiso 1 1 calc R . . H8C H 0.5027 0.9719 0.2924 0.030 Uiso 1 1 calc R . . C9 C -0.11120(14) 0.87380(14) 0.37361(6) 0.0189(3) Uani 1 1 d . . . C10 C -0.14077(16) 1.02032(15) 0.40552(6) 0.0254(3) Uani 1 1 d . . . H10A H -0.1727 1.0022 0.4491 0.038 Uiso 1 1 calc R . . H10B H -0.2252 1.0743 0.3824 0.038 Uiso 1 1 calc R . . H10C H -0.0438 1.0805 0.4060 0.038 Uiso 1 1 calc R . . C11 C -0.50091(14) 0.77852(14) 0.04232(6) 0.0178(3) Uani 1 1 d . . . C12 C -0.55952(15) 0.70551(15) -0.01119(6) 0.0212(3) Uani 1 1 d . . . H12A H -0.5019 0.6271 -0.0305 0.025 Uiso 1 1 calc R . . C13 C -0.70662(16) 0.75166(15) -0.03567(6) 0.0233(3) Uani 1 1 d . . . H13A H -0.7512 0.7025 -0.0719 0.028 Uiso 1 1 calc R . . C14 C -0.78927(15) 0.86853(15) -0.00793(6) 0.0223(3) Uani 1 1 d . . . H14A H -0.8901 0.8964 -0.0251 0.027 Uiso 1 1 calc R . . C15 C -0.72689(15) 0.94532(14) 0.04461(6) 0.0200(3) Uani 1 1 d . . . H15A H -0.7808 1.0278 0.0626 0.024 Uiso 1 1 calc R . . C16 C -0.58300(14) 0.89593(14) 0.06931(6) 0.0175(3) Uani 1 1 d . . . C17 C -0.35376(14) 0.75145(13) 0.08164(6) 0.0177(3) Uani 1 1 d . . . C18 C -0.49109(14) 0.94826(13) 0.12618(6) 0.0171(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0190(4) 0.0219(5) 0.0228(5) -0.0020(4) 0.0012(4) 0.0031(3) O2 0.0152(4) 0.0195(4) 0.0185(5) -0.0021(3) -0.0014(3) 0.0000(3) O3 0.0378(6) 0.0249(5) 0.0195(5) 0.0032(4) -0.0023(4) 0.0012(4) O4 0.0184(4) 0.0161(4) 0.0163(5) -0.0006(3) -0.0003(3) 0.0016(3) O5 0.0218(5) 0.0256(5) 0.0239(5) -0.0037(4) -0.0009(4) 0.0064(4) O6 0.0273(5) 0.0185(5) 0.0214(5) -0.0034(4) -0.0033(4) 0.0039(4) N1 0.0171(5) 0.0171(5) 0.0170(6) -0.0010(4) -0.0024(4) 0.0004(4) C1 0.0232(6) 0.0178(6) 0.0168(7) 0.0020(5) -0.0021(5) -0.0044(5) C2 0.0186(6) 0.0182(6) 0.0183(7) -0.0009(5) 0.0022(5) -0.0040(5) C3 0.0165(6) 0.0157(6) 0.0171(6) -0.0025(5) -0.0022(5) -0.0003(5) C4 0.0187(6) 0.0132(6) 0.0175(7) -0.0005(4) 0.0003(5) 0.0008(4) C5 0.0162(6) 0.0161(6) 0.0186(7) -0.0001(5) 0.0002(5) -0.0015(4) C6 0.0177(6) 0.0168(6) 0.0176(7) -0.0013(5) -0.0035(5) -0.0009(5) C7 0.0166(6) 0.0147(6) 0.0205(7) 0.0041(5) 0.0002(5) 0.0021(5) C8 0.0163(6) 0.0194(6) 0.0240(7) 0.0009(5) -0.0014(5) 0.0004(5) C9 0.0145(6) 0.0240(7) 0.0182(7) 0.0011(5) 0.0003(5) -0.0020(5) C10 0.0277(7) 0.0274(7) 0.0212(7) -0.0038(5) 0.0021(5) 0.0001(6) C11 0.0177(6) 0.0184(6) 0.0174(7) 0.0024(5) 0.0015(5) -0.0014(5) C12 0.0233(6) 0.0223(6) 0.0181(7) -0.0017(5) 0.0010(5) -0.0005(5) C13 0.0249(7) 0.0287(7) 0.0162(7) -0.0012(5) -0.0026(5) -0.0032(5) C14 0.0190(6) 0.0294(7) 0.0184(7) 0.0054(5) -0.0020(5) 0.0000(5) C15 0.0206(6) 0.0216(6) 0.0177(7) 0.0033(5) 0.0015(5) 0.0020(5) C16 0.0188(6) 0.0178(6) 0.0160(6) 0.0028(5) 0.0014(5) -0.0017(5) C17 0.0183(6) 0.0177(6) 0.0173(7) 0.0006(5) 0.0014(5) -0.0015(5) C18 0.0182(6) 0.0151(6) 0.0179(7) 0.0029(5) 0.0002(5) -0.0006(5) _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 C7 1.2072(15) . ? O2 C7 1.3580(15) . ? O2 C3 1.4576(14) . ? O3 C9 1.2044(16) . ? O4 C9 1.3562(16) . ? O4 C4 1.4539(14) . ? O5 C17 1.2110(15) . ? O6 C18 1.2101(15) . ? N1 C17 1.3988(16) . ? N1 C18 1.4009(16) . ? N1 C6 1.4675(15) . ? C1 C2 1.3229(18) . ? C1 C6 1.5032(17) . ? C1 H1A 0.9500 . ? C2 C3 1.5014(17) . ? C2 H2A 0.9500 . ? C3 C4 1.5223(17) . ? C3 H3A 1.0000 . ? C4 C5 1.5205(17) . ? C4 H4A 1.0000 . ? C5 C6 1.5325(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 1.0000 . ? C7 C8 1.4998(17) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.4947(18) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3834(18) . ? C11 C16 1.3876(18) . ? C11 C17 1.4954(17) . ? C12 C13 1.3951(19) . ? C12 H12A 0.9500 . ? C13 C14 1.3931(19) . ? C13 H13A 0.9500 . ? C14 C15 1.3944(19) . ? C14 H14A 0.9500 . ? C15 C16 1.3819(18) . ? C15 H15A 0.9500 . ? C16 C18 1.4864(17) . ? 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 C7 O2 C3 115.12(9) . . ? C9 O4 C4 116.56(9) . . ? C17 N1 C18 111.81(10) . . ? C17 N1 C6 126.08(10) . . ? C18 N1 C6 122.10(10) . . ? C2 C1 C6 122.97(12) . . ? C2 C1 H1A 118.5 . . ? C6 C1 H1A 118.5 . . ? C1 C2 C3 123.40(11) . . ? C1 C2 H2A 118.3 . . ? C3 C2 H2A 118.3 . . ? O2 C3 C2 109.14(9) . . ? O2 C3 C4 107.80(9) . . ? C2 C3 C4 112.80(10) . . ? O2 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? O4 C4 C5 108.36(9) . . ? O4 C4 C3 109.87(9) . . ? C5 C4 C3 109.60(10) . . ? O4 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C4 C5 C6 110.02(10) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C1 111.53(10) . . ? N1 C6 C5 112.75(10) . . ? C1 C6 C5 110.71(10) . . ? N1 C6 H6A 107.2 . . ? C1 C6 H6A 107.2 . . ? C5 C6 H6A 107.2 . . ? O1 C7 O2 122.88(11) . . ? O1 C7 C8 125.35(11) . . ? O2 C7 C8 111.76(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 O4 123.61(12) . . ? O3 C9 C10 124.95(12) . . ? O4 C9 C10 111.44(11) . . ? 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 C16 121.26(12) . . ? C12 C11 C17 130.56(12) . . ? C16 C11 C17 108.16(11) . . ? C11 C12 C13 117.28(12) . . ? C11 C12 H12A 121.4 . . ? C13 C12 H12A 121.4 . . ? C14 C13 C12 121.17(12) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 121.27(12) . . ? C13 C14 H14A 119.4 . . ? C15 C14 H14A 119.4 . . ? C16 C15 C14 116.91(12) . . ? C16 C15 H15A 121.5 . . ? C14 C15 H15A 121.5 . . ? C15 C16 C11 122.06(12) . . ? C15 C16 C18 129.72(12) . . ? C11 C16 C18 108.21(11) . . ? O5 C17 N1 125.60(11) . . ? O5 C17 C11 128.65(11) . . ? N1 C17 C11 105.74(10) . . ? O6 C18 N1 125.26(11) . . ? O6 C18 C16 128.67(11) . . ? N1 C18 C16 106.07(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.36(19) . . . . ? C7 O2 C3 C2 -73.67(12) . . . . ? C7 O2 C3 C4 163.49(9) . . . . ? C1 C2 C3 O2 -133.40(12) . . . . ? C1 C2 C3 C4 -13.61(17) . . . . ? C9 O4 C4 C5 131.24(10) . . . . ? C9 O4 C4 C3 -109.04(11) . . . . ? O2 C3 C4 O4 45.39(12) . . . . ? C2 C3 C4 O4 -75.17(12) . . . . ? O2 C3 C4 C5 164.36(9) . . . . ? C2 C3 C4 C5 43.79(13) . . . . ? O4 C4 C5 C6 56.59(12) . . . . ? C3 C4 C5 C6 -63.31(12) . . . . ? C17 N1 C6 C1 63.91(15) . . . . ? C18 N1 C6 C1 -117.52(12) . . . . ? C17 N1 C6 C5 -61.37(15) . . . . ? C18 N1 C6 C5 117.20(12) . . . . ? C2 C1 C6 N1 -146.25(12) . . . . ? C2 C1 C6 C5 -19.83(17) . . . . ? C4 C5 C6 N1 175.93(10) . . . . ? C4 C5 C6 C1 50.20(13) . . . . ? C3 O2 C7 O1 -6.76(16) . . . . ? C3 O2 C7 C8 172.20(9) . . . . ? C4 O4 C9 O3 -1.32(17) . . . . ? C4 O4 C9 C10 178.05(10) . . . . ? C16 C11 C12 C13 -1.95(18) . . . . ? C17 C11 C12 C13 176.41(12) . . . . ? C11 C12 C13 C14 1.23(19) . . . . ? C12 C13 C14 C15 1.1(2) . . . . ? C13 C14 C15 C16 -2.66(19) . . . . ? C14 C15 C16 C11 1.96(18) . . . . ? C14 C15 C16 C18 -176.49(12) . . . . ? C12 C11 C16 C15 0.35(19) . . . . ? C17 C11 C16 C15 -178.34(11) . . . . ? C12 C11 C16 C18 179.09(11) . . . . ? C17 C11 C16 C18 0.40(13) . . . . ? C18 N1 C17 O5 -178.82(12) . . . . ? C6 N1 C17 O5 -0.13(19) . . . . ? C18 N1 C17 C11 0.15(13) . . . . ? C6 N1 C17 C11 178.85(10) . . . . ? C12 C11 C17 O5 0.1(2) . . . . ? C16 C11 C17 O5 178.59(12) . . . . ? C12 C11 C17 N1 -178.87(12) . . . . ? C16 C11 C17 N1 -0.35(13) . . . . ? C17 N1 C18 O6 179.92(11) . . . . ? C6 N1 C18 O6 1.16(19) . . . . ? C17 N1 C18 C16 0.09(13) . . . . ? C6 N1 C18 C16 -178.67(10) . . . . ? C15 C16 C18 O6 -1.5(2) . . . . ? C11 C16 C18 O6 179.87(12) . . . . ? C15 C16 C18 N1 178.30(12) . . . . ? C11 C16 C18 N1 -0.31(13) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.86 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.268 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 data_donu _database_code_depnum_ccdc_archive 'CCDC 767847' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N O4' _chemical_formula_weight 257.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2217(2) _cell_length_b 6.91770(10) _cell_length_c 14.8259(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.3860(10) _cell_angle_gamma 90.00 _cell_volume 1104.16(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6297 _cell_measurement_theta_min 4 _cell_measurement_theta_max 67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8309 _exptl_absorpt_correction_T_max 0.9184 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9222 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 67.93 _reflns_number_total 1969 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0526P)^2^+0.5682P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1969 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.94222(9) -0.01412(14) 0.37163(7) 0.0238(3) Uani 1 1 d . . . O2 O 0.95253(8) 0.09108(14) 0.28561(6) 0.0235(3) Uani 1 1 d . . . O3 O 0.47597(8) 0.05066(14) 0.23777(6) 0.0204(2) Uani 1 1 d . . . O4 O 0.71748(8) 0.21093(13) 0.53243(6) 0.0198(2) Uani 1 1 d . . . N1 N 0.62503(9) 0.13330(15) 0.37514(7) 0.0153(3) Uani 1 1 d . . . C1 C 0.85742(12) 0.0872(2) 0.41385(9) 0.0185(3) Uani 1 1 d . . . C2 C 0.89782(11) 0.2937(2) 0.43121(9) 0.0196(3) Uani 1 1 d . . . C3 C 0.90437(11) 0.3844(2) 0.35381(9) 0.0198(3) Uani 1 1 d . . . C4 C 0.86912(12) 0.25641(19) 0.26857(9) 0.0190(3) Uani 1 1 d . . . C5 C 0.73629(12) 0.18238(19) 0.25220(9) 0.0166(3) Uani 1 1 d . . . C6 C 0.72957(11) 0.06910(18) 0.34071(8) 0.0163(3) Uani 1 1 d . . . C7 C 0.50354(11) 0.11506(17) 0.31720(9) 0.0161(3) Uani 1 1 d . . . C8 C 0.62657(11) 0.19326(17) 0.46603(9) 0.0154(3) Uani 1 1 d . . . C11 C 0.42066(11) 0.18170(17) 0.37303(9) 0.0165(3) Uani 1 1 d . . . C12 C 0.29239(12) 0.19892(19) 0.34899(10) 0.0198(3) Uani 1 1 d . . . C13 C 0.24057(12) 0.26634(19) 0.41804(10) 0.0223(3) Uani 1 1 d . . . C14 C 0.31475(12) 0.31342(19) 0.50770(10) 0.0213(3) Uani 1 1 d . . . C15 C 0.44385(12) 0.29337(18) 0.53171(9) 0.0183(3) Uani 1 1 d . . . C16 C 0.49423(11) 0.22751(17) 0.46235(9) 0.0157(3) Uani 1 1 d . . . H1 H 0.8629(13) 0.015(2) 0.4692(10) 0.013(3) Uiso 1 1 d . . . H2 H 0.9183(14) 0.348(2) 0.4933(11) 0.020(4) Uiso 1 1 d . . . H3 H 0.9308(15) 0.516(2) 0.3492(11) 0.025(4) Uiso 1 1 d . . . H4 H 0.8829(13) 0.312(2) 0.2110(11) 0.015(4) Uiso 1 1 d . . . H5A H 0.6810(13) 0.290(2) 0.2410(10) 0.013(3) Uiso 1 1 d . . . H5B H 0.7157(14) 0.099(2) 0.1968(11) 0.018(4) Uiso 1 1 d . . . H6 H 0.7176(12) -0.068(2) 0.3266(9) 0.010(3) Uiso 1 1 d . . . H12 H 0.2413(15) 0.167(2) 0.2886(12) 0.025(4) Uiso 1 1 d . . . H13 H 0.1513(16) 0.279(2) 0.4025(11) 0.023(4) Uiso 1 1 d . . . H14 H 0.2752(16) 0.363(2) 0.5541(11) 0.026(4) Uiso 1 1 d . . . H15 H 0.4950(15) 0.329(2) 0.5934(12) 0.021(4) 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 0.0226(5) 0.0279(5) 0.0234(5) 0.0067(4) 0.0105(4) 0.0104(4) O2 0.0215(5) 0.0317(5) 0.0205(5) 0.0036(4) 0.0111(4) 0.0079(4) O3 0.0215(5) 0.0240(5) 0.0158(5) -0.0015(4) 0.0054(4) -0.0048(4) O4 0.0172(5) 0.0257(5) 0.0157(5) -0.0008(4) 0.0031(4) 0.0007(4) N1 0.0145(5) 0.0170(5) 0.0150(5) 0.0006(4) 0.0052(4) 0.0002(4) C1 0.0164(6) 0.0239(7) 0.0164(6) 0.0027(5) 0.0067(5) 0.0045(5) C2 0.0115(6) 0.0282(7) 0.0183(7) -0.0030(5) 0.0029(5) 0.0004(5) C3 0.0127(6) 0.0239(7) 0.0228(7) -0.0010(5) 0.0051(5) -0.0019(5) C4 0.0168(6) 0.0232(7) 0.0186(7) 0.0029(5) 0.0075(5) 0.0025(5) C5 0.0156(6) 0.0189(6) 0.0159(6) -0.0001(5) 0.0051(5) 0.0011(5) C6 0.0169(6) 0.0163(6) 0.0169(6) -0.0004(5) 0.0068(5) 0.0014(5) C7 0.0178(6) 0.0142(6) 0.0164(6) 0.0030(5) 0.0048(5) -0.0019(5) C8 0.0176(6) 0.0135(6) 0.0161(6) 0.0021(5) 0.0063(5) -0.0002(5) C11 0.0175(6) 0.0132(6) 0.0193(6) 0.0037(5) 0.0061(5) -0.0010(5) C12 0.0168(6) 0.0194(6) 0.0219(7) 0.0044(5) 0.0035(5) -0.0021(5) C13 0.0164(7) 0.0206(7) 0.0315(7) 0.0071(6) 0.0096(6) 0.0024(5) C14 0.0237(7) 0.0164(6) 0.0283(7) 0.0035(5) 0.0147(6) 0.0027(5) C15 0.0218(7) 0.0153(6) 0.0196(7) 0.0015(5) 0.0087(5) 0.0001(5) C16 0.0170(6) 0.0123(6) 0.0186(6) 0.0030(5) 0.0064(5) 0.0001(5) _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 1.4577(15) . ? O1 O2 1.5009(13) . ? O2 C4 1.4542(16) . ? O3 C7 1.2146(16) . ? O4 C8 1.2076(16) . ? N1 C7 1.3970(16) . ? N1 C8 1.4054(16) . ? N1 C6 1.4736(16) . ? C1 C2 1.4988(19) . ? C1 C6 1.5402(17) . ? C1 H1 0.948(15) . ? C2 C3 1.3279(19) . ? C2 H2 0.960(16) . ? C3 C4 1.5018(18) . ? C3 H3 0.969(17) . ? C4 C5 1.5294(17) . ? C4 H4 0.987(15) . ? C5 C6 1.5485(17) . ? C5 H5A 0.953(15) . ? C5 H5B 0.976(16) . ? C6 H6 0.970(15) . ? C7 C11 1.4822(17) . ? C8 C16 1.4896(17) . ? C11 C16 1.3852(18) . ? C11 C12 1.3870(18) . ? C12 C13 1.3926(19) . ? C12 H12 0.943(17) . ? C13 C14 1.393(2) . ? C13 H13 0.966(17) . ? C14 C15 1.3978(19) . ? C14 H14 0.979(17) . ? C15 C16 1.3829(18) . ? C15 H15 0.965(17) . ? 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 O2 110.36(8) . . ? C4 O2 O1 109.19(8) . . ? C7 N1 C8 111.23(10) . . ? C7 N1 C6 119.60(10) . . ? C8 N1 C6 128.71(10) . . ? O1 C1 C2 109.24(10) . . ? O1 C1 C6 104.46(10) . . ? C2 C1 C6 112.03(11) . . ? O1 C1 H1 103.2(9) . . ? C2 C1 H1 114.3(9) . . ? C6 C1 H1 112.7(9) . . ? C3 C2 C1 112.94(12) . . ? C3 C2 H2 125.9(9) . . ? C1 C2 H2 121.2(9) . . ? C2 C3 C4 112.51(12) . . ? C2 C3 H3 126.8(9) . . ? C4 C3 H3 120.6(9) . . ? O2 C4 C3 108.29(10) . . ? O2 C4 C5 108.36(10) . . ? C3 C4 C5 110.15(10) . . ? O2 C4 H4 102.0(8) . . ? C3 C4 H4 115.4(9) . . ? C5 C4 H4 112.1(8) . . ? C4 C5 C6 108.25(10) . . ? C4 C5 H5A 108.9(9) . . ? C6 C5 H5A 111.0(8) . . ? C4 C5 H5B 108.6(9) . . ? C6 C5 H5B 111.0(9) . . ? H5A C5 H5B 109.0(12) . . ? N1 C6 C1 113.96(10) . . ? N1 C6 C5 112.01(10) . . ? C1 C6 C5 107.28(10) . . ? N1 C6 H6 107.0(8) . . ? C1 C6 H6 106.0(8) . . ? C5 C6 H6 110.3(8) . . ? O3 C7 N1 124.52(11) . . ? O3 C7 C11 128.84(12) . . ? N1 C7 C11 106.61(10) . . ? O4 C8 N1 126.20(11) . . ? O4 C8 C16 128.16(12) . . ? N1 C8 C16 105.63(10) . . ? C16 C11 C12 121.43(12) . . ? C16 C11 C7 107.84(11) . . ? C12 C11 C7 130.72(12) . . ? C11 C12 C13 117.27(12) . . ? C11 C12 H12 122.2(10) . . ? C13 C12 H12 120.6(10) . . ? C12 C13 C14 121.24(12) . . ? C12 C13 H13 118.3(9) . . ? C14 C13 H13 120.5(9) . . ? C13 C14 C15 121.13(12) . . ? C13 C14 H14 119.0(10) . . ? C15 C14 H14 119.9(10) . . ? C16 C15 C14 117.07(12) . . ? C16 C15 H15 122.0(9) . . ? C14 C15 H15 120.8(9) . . ? C15 C16 C11 121.86(12) . . ? C15 C16 C8 129.62(12) . . ? C11 C16 C8 108.52(11) . . ? 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 C1 O1 O2 C4 -3.00(12) . . . . ? O2 O1 C1 C2 -53.78(12) . . . . ? O2 O1 C1 C6 66.23(11) . . . . ? O1 C1 C2 C3 56.94(14) . . . . ? C6 C1 C2 C3 -58.31(14) . . . . ? C1 C2 C3 C4 0.17(15) . . . . ? O1 O2 C4 C3 58.60(12) . . . . ? O1 O2 C4 C5 -60.87(12) . . . . ? C2 C3 C4 O2 -58.98(14) . . . . ? C2 C3 C4 C5 59.36(14) . . . . ? O2 C4 C5 C6 59.23(13) . . . . ? C3 C4 C5 C6 -59.06(13) . . . . ? C7 N1 C6 C1 -176.75(10) . . . . ? C8 N1 C6 C1 -5.28(18) . . . . ? C7 N1 C6 C5 61.22(14) . . . . ? C8 N1 C6 C5 -127.31(13) . . . . ? O1 C1 C6 N1 170.25(10) . . . . ? C2 C1 C6 N1 -71.62(13) . . . . ? O1 C1 C6 C5 -65.15(12) . . . . ? C2 C1 C6 C5 52.98(13) . . . . ? C4 C5 C6 N1 129.68(11) . . . . ? C4 C5 C6 C1 3.92(13) . . . . ? C8 N1 C7 O3 -173.80(11) . . . . ? C6 N1 C7 O3 -0.93(18) . . . . ? C8 N1 C7 C11 4.25(13) . . . . ? C6 N1 C7 C11 177.11(10) . . . . ? C7 N1 C8 O4 175.62(12) . . . . ? C6 N1 C8 O4 3.6(2) . . . . ? C7 N1 C8 C16 -3.90(13) . . . . ? C6 N1 C8 C16 -175.94(11) . . . . ? O3 C7 C11 C16 175.07(12) . . . . ? N1 C7 C11 C16 -2.86(13) . . . . ? O3 C7 C11 C12 -4.1(2) . . . . ? N1 C7 C11 C12 178.00(12) . . . . ? C16 C11 C12 C13 0.72(18) . . . . ? C7 C11 C12 C13 179.76(12) . . . . ? C11 C12 C13 C14 -0.35(19) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C13 C14 C15 C16 0.84(19) . . . . ? C14 C15 C16 C11 -0.47(18) . . . . ? C14 C15 C16 C8 179.43(12) . . . . ? C12 C11 C16 C15 -0.32(19) . . . . ? C7 C11 C16 C15 -179.55(11) . . . . ? C12 C11 C16 C8 179.76(11) . . . . ? C7 C11 C16 C8 0.53(13) . . . . ? O4 C8 C16 C15 2.6(2) . . . . ? N1 C8 C16 C15 -177.94(12) . . . . ? O4 C8 C16 C11 -177.53(12) . . . . ? N1 C8 C16 C11 1.97(13) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 67.93 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.256 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.040 data_donv _database_code_depnum_ccdc_archive 'CCDC 767848' #TrackingRef 'CCDC 767848 revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration unk _chemical_formula_sum 'C14 H11 N O4' _chemical_formula_weight 257.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.77800(10) _cell_length_b 8.5059(2) _cell_length_c 19.6445(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1132.56(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 5 _cell_measurement_theta_max 67 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8721 _exptl_absorpt_correction_T_max 0.9724 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9242 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 67.63 _reflns_number_total 1191 _reflns_number_gt 1145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0572P)^2^+0.3062P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(3) _refine_ls_number_reflns 1191 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.7188(2) 0.49683(18) 0.20363(7) 0.0246(4) Uani 1 1 d . . . O2 O 0.6032(2) 0.40112(17) 0.25400(7) 0.0266(4) Uani 1 1 d . . . O3 O 0.2898(2) 0.48427(17) 0.12256(7) 0.0220(3) Uani 1 1 d . . . O4 O 0.8111(2) 0.36468(18) -0.01759(7) 0.0252(4) Uani 1 1 d . . . N1 N 0.5751(3) 0.39995(19) 0.06631(8) 0.0167(4) Uani 1 1 d . . . C1 C 0.8274(3) 0.3934(2) 0.15869(10) 0.0202(4) Uani 1 1 d . . . H1A H 0.9160 0.4560 0.1284 0.024 Uiso 1 1 calc R . . C2 C 0.9456(3) 0.2792(2) 0.19979(10) 0.0231(5) Uani 1 1 d . . . H2A H 1.0850 0.2697 0.1965 0.028 Uiso 1 1 calc R . . C3 C 0.8368(3) 0.1935(3) 0.24090(10) 0.0227(5) Uani 1 1 d . . . H3A H 0.8885 0.1140 0.2698 0.027 Uiso 1 1 calc R . . C4 C 0.6224(3) 0.2350(2) 0.23725(11) 0.0224(5) Uani 1 1 d . . . H4A H 0.5460 0.1701 0.2705 0.027 Uiso 1 1 calc R . . C5 C 0.5428(3) 0.2091(2) 0.16544(9) 0.0213(4) Uani 1 1 d . . . H5A H 0.4058 0.2487 0.1620 0.026 Uiso 1 1 calc R . . H5B H 0.5429 0.0956 0.1543 0.026 Uiso 1 1 calc R . . C6 C 0.6780(3) 0.2994(2) 0.11579(10) 0.0192(4) Uani 1 1 d . . . H6A H 0.7543 0.2194 0.0893 0.023 Uiso 1 1 calc R . . C7 C 0.3916(3) 0.4742(2) 0.07219(10) 0.0179(4) Uani 1 1 d . . . C8 C 0.6543(3) 0.4188(2) 0.00081(10) 0.0185(4) Uani 1 1 d . . . C11 C 0.3506(3) 0.5445(2) 0.00381(10) 0.0176(4) Uani 1 1 d . . . C12 C 0.1871(3) 0.6264(2) -0.01777(10) 0.0213(4) Uani 1 1 d . . . H12A H 0.0783 0.6454 0.0116 0.026 Uiso 1 1 calc R . . C13 C 0.1892(3) 0.6809(2) -0.08545(10) 0.0234(5) Uani 1 1 d . . . H13A H 0.0790 0.7374 -0.1026 0.028 Uiso 1 1 calc R . . C14 C 0.3503(4) 0.6530(2) -0.12740(10) 0.0243(5) Uani 1 1 d . . . H14A H 0.3485 0.6922 -0.1727 0.029 Uiso 1 1 calc R . . C15 C 0.5146(3) 0.5689(2) -0.10502(10) 0.0222(5) Uani 1 1 d . . . H15A H 0.6245 0.5500 -0.1339 0.027 Uiso 1 1 calc R . . C16 C 0.5098(3) 0.5141(2) -0.03825(10) 0.0186(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0287(8) 0.0178(7) 0.0274(7) -0.0015(6) 0.0045(7) -0.0041(7) O2 0.0291(8) 0.0248(7) 0.0259(8) -0.0028(6) 0.0107(7) -0.0009(7) O3 0.0209(7) 0.0258(7) 0.0191(7) 0.0009(6) 0.0056(6) 0.0033(7) O4 0.0228(8) 0.0289(8) 0.0239(7) 0.0011(6) 0.0062(6) 0.0054(7) N1 0.0164(8) 0.0174(8) 0.0164(8) -0.0006(6) 0.0004(6) -0.0001(7) C1 0.0163(9) 0.0231(10) 0.0213(9) 0.0026(9) 0.0026(8) -0.0030(9) C2 0.0175(10) 0.0290(10) 0.0227(10) -0.0044(9) -0.0023(9) 0.0022(10) C3 0.0279(12) 0.0218(10) 0.0182(9) 0.0003(8) -0.0051(9) 0.0009(10) C4 0.0260(11) 0.0211(10) 0.0203(9) 0.0012(8) 0.0033(9) -0.0019(9) C5 0.0203(10) 0.0201(9) 0.0235(10) 0.0027(8) 0.0002(9) -0.0015(9) C6 0.0198(10) 0.0176(9) 0.0201(10) 0.0004(8) 0.0000(9) 0.0024(9) C7 0.0187(9) 0.0151(9) 0.0200(10) -0.0023(8) -0.0002(8) -0.0025(8) C8 0.0186(10) 0.0171(9) 0.0199(10) -0.0028(8) 0.0020(8) -0.0034(8) C11 0.0208(10) 0.0149(9) 0.0172(9) -0.0016(7) -0.0015(8) -0.0041(8) C12 0.0239(10) 0.0178(9) 0.0222(9) -0.0020(8) 0.0008(9) 0.0001(9) C13 0.0286(11) 0.0177(10) 0.0239(10) -0.0002(8) -0.0022(10) 0.0030(9) C14 0.0341(12) 0.0213(10) 0.0174(9) 0.0008(8) -0.0036(9) -0.0024(10) C15 0.0276(11) 0.0207(10) 0.0183(9) -0.0022(8) 0.0047(8) -0.0032(9) C16 0.0199(10) 0.0155(9) 0.0205(10) -0.0028(8) 0.0012(8) -0.0030(8) _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 1.448(3) . ? O1 O2 1.502(2) . ? O2 C4 1.456(3) . ? O3 C7 1.209(2) . ? O4 C8 1.213(3) . ? N1 C7 1.400(3) . ? N1 C8 1.403(2) . ? N1 C6 1.471(3) . ? C1 C2 1.496(3) . ? C1 C6 1.541(3) . ? C1 H1A 1.0000 . ? C2 C3 1.315(3) . ? C2 H2A 0.9500 . ? C3 C4 1.497(3) . ? C3 H3A 0.9500 . ? C4 C5 1.526(3) . ? C4 H4A 1.0000 . ? C5 C6 1.543(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 1.0000 . ? C7 C11 1.496(3) . ? C8 C16 1.485(3) . ? C11 C12 1.376(3) . ? C11 C16 1.383(3) . ? C12 C13 1.408(3) . ? C12 H12A 0.9500 . ? C13 C14 1.388(3) . ? C13 H13A 0.9500 . ? C14 C15 1.395(3) . ? C14 H14A 0.9500 . ? C15 C16 1.392(3) . ? C15 H15A 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 O2 109.72(14) . . ? C4 O2 O1 109.30(14) . . ? C7 N1 C8 111.34(16) . . ? C7 N1 C6 128.99(16) . . ? C8 N1 C6 119.42(16) . . ? O1 C1 C2 109.76(16) . . ? O1 C1 C6 108.34(16) . . ? C2 C1 C6 108.10(17) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? C6 C1 H1A 110.2 . . ? C3 C2 C1 113.01(19) . . ? C3 C2 H2A 123.5 . . ? C1 C2 H2A 123.5 . . ? C2 C3 C4 112.62(19) . . ? C2 C3 H3A 123.7 . . ? C4 C3 H3A 123.7 . . ? O2 C4 C3 107.72(18) . . ? O2 C4 C5 108.50(17) . . ? C3 C4 C5 110.70(18) . . ? O2 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? C5 C4 H4A 110.0 . . ? C4 C5 C6 107.61(17) . . ? C4 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? C4 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? N1 C6 C1 111.80(16) . . ? N1 C6 C5 115.20(17) . . ? C1 C6 C5 107.61(15) . . ? N1 C6 H6A 107.3 . . ? C1 C6 H6A 107.3 . . ? C5 C6 H6A 107.3 . . ? O3 C7 N1 127.33(18) . . ? O3 C7 C11 126.89(18) . . ? N1 C7 C11 105.74(16) . . ? O4 C8 N1 124.38(19) . . ? O4 C8 C16 129.13(19) . . ? N1 C8 C16 106.49(16) . . ? C12 C11 C16 122.60(18) . . ? C12 C11 C7 128.95(19) . . ? C16 C11 C7 108.45(17) . . ? C11 C12 C13 116.7(2) . . ? C11 C12 H12A 121.6 . . ? C13 C12 H12A 121.6 . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 121.92(19) . . ? C13 C14 H14A 119.0 . . ? C15 C14 H14A 119.0 . . ? C16 C15 C14 116.7(2) . . ? C16 C15 H15A 121.6 . . ? C14 C15 H15A 121.6 . . ? C11 C16 C15 121.23(19) . . ? C11 C16 C8 107.94(17) . . ? C15 C16 C8 130.83(19) . . ? 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 C1 O1 O2 C4 -5.5(2) . . . . ? O2 O1 C1 C2 -52.3(2) . . . . ? O2 O1 C1 C6 65.56(18) . . . . ? O1 C1 C2 C3 58.3(2) . . . . ? C6 C1 C2 C3 -59.7(2) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? O1 O2 C4 C3 60.2(2) . . . . ? O1 O2 C4 C5 -59.7(2) . . . . ? C2 C3 C4 O2 -58.0(2) . . . . ? C2 C3 C4 C5 60.5(2) . . . . ? O2 C4 C5 C6 64.9(2) . . . . ? C3 C4 C5 C6 -53.1(2) . . . . ? C7 N1 C6 C1 -95.7(2) . . . . ? C8 N1 C6 C1 90.6(2) . . . . ? C7 N1 C6 C5 27.6(3) . . . . ? C8 N1 C6 C5 -146.16(17) . . . . ? O1 C1 C6 N1 69.5(2) . . . . ? C2 C1 C6 N1 -171.61(16) . . . . ? O1 C1 C6 C5 -57.9(2) . . . . ? C2 C1 C6 C5 60.9(2) . . . . ? C4 C5 C6 N1 -130.99(18) . . . . ? C4 C5 C6 C1 -5.5(2) . . . . ? C8 N1 C7 O3 -177.02(19) . . . . ? C6 N1 C7 O3 8.8(3) . . . . ? C8 N1 C7 C11 0.8(2) . . . . ? C6 N1 C7 C11 -173.40(17) . . . . ? C7 N1 C8 O4 -179.37(18) . . . . ? C6 N1 C8 O4 -4.6(3) . . . . ? C7 N1 C8 C16 0.4(2) . . . . ? C6 N1 C8 C16 175.21(16) . . . . ? O3 C7 C11 C12 -4.1(3) . . . . ? N1 C7 C11 C12 178.14(18) . . . . ? O3 C7 C11 C16 176.05(19) . . . . ? N1 C7 C11 C16 -1.7(2) . . . . ? C16 C11 C12 C13 -0.7(3) . . . . ? C7 C11 C12 C13 179.41(19) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C12 C11 C16 C15 1.5(3) . . . . ? C7 C11 C16 C15 -178.56(18) . . . . ? C12 C11 C16 C8 -177.89(18) . . . . ? C7 C11 C16 C8 2.0(2) . . . . ? C14 C15 C16 C11 -1.1(3) . . . . ? C14 C15 C16 C8 178.18(19) . . . . ? O4 C8 C16 C11 178.2(2) . . . . ? N1 C8 C16 C11 -1.5(2) . . . . ? O4 C8 C16 C15 -1.1(3) . . . . ? N1 C8 C16 C15 179.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 67.63 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.176 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.037 data_don1a _database_code_depnum_ccdc_archive 'CCDC 768802' #TrackingRef 'N-(2,3-epoxy-4R,5S-dihydroxycyclohex-1R-yl)phthalimide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.2305(4) _cell_length_b 20.6353(11) _cell_length_c 8.5115(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.012(4) _cell_angle_gamma 90.00 _cell_volume 1232.16(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3358 _cell_measurement_theta_min 4 _cell_measurement_theta_max 66 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8021 _exptl_absorpt_correction_T_max 0.9626 _exptl_absorpt_process_details ; SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10020 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 67.47 _reflns_number_total 2145 _reflns_number_gt 1852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)' _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)' _computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)' _computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF-2008/2 (Bruker, 2008)' _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^)+(0.0416P)^2^+0.8408P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0004(1) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2145 _refine_ls_number_parameters 251 _refine_ls_number_restraints 56 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.005 _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 0.17477(19) 0.15949(6) 0.16497(18) 0.0286(3) Uani 0.9202(14) 1 d PD A 1 O2 O 0.2767(2) -0.02164(6) 0.48384(16) 0.0298(4) Uani 0.9202(14) 1 d PD A 1 O3 O 0.3838(2) 0.18148(7) 0.71859(16) 0.0311(4) Uani 0.9202(14) 1 d PD A 1 O4 O 0.0975(2) 0.29751(7) 0.70939(19) 0.0270(3) Uani 0.9202(14) 1 d PD A 1 H4O H 0.160(3) 0.2852(12) 0.794(3) 0.024(7) Uiso 0.9202(14) 1 d P A 1 O5 O -0.2206(3) 0.21912(12) 0.5437(2) 0.0306(5) Uani 0.9202(14) 1 d PD A 1 H5O H -0.226(4) 0.2544(15) 0.598(3) 0.058(8) Uiso 0.9202(14) 1 d P A 1 N1 N 0.2158(2) 0.07786(9) 0.3566(2) 0.0226(4) Uani 0.9202(14) 1 d PD A 1 C1 C 0.2341(12) 0.04722(11) 0.1009(3) 0.0233(7) Uani 0.9202(14) 1 d PD A 1 C2 C 0.2340(3) 0.04488(12) -0.0612(2) 0.0274(5) Uani 0.9202(14) 1 d PD A 1 H2A H 0.2155 0.0828 -0.1265 0.033 Uiso 0.9202(14) 1 calc PR A 1 C3 C 0.2620(3) -0.01536(13) -0.1244(2) 0.0304(5) Uani 0.9202(14) 1 d PD A 1 H3A H 0.2620 -0.0188 -0.2357 0.037 Uiso 0.9202(14) 1 calc PR A 1 C4 C 0.2901(3) -0.07078(12) -0.0289(3) 0.0297(5) Uani 0.9202(14) 1 d PD A 1 H4A H 0.3087 -0.1112 -0.0761 0.036 Uiso 0.9202(14) 1 calc PR A 1 C5 C 0.2914(3) -0.06799(10) 0.1350(3) 0.0262(5) Uani 0.9202(14) 1 d PD A 1 H5A H 0.3107 -0.1057 0.2010 0.031 Uiso 0.9202(14) 1 calc PR A 1 C6 C 0.2633(8) -0.00779(12) 0.1972(3) 0.0226(5) Uani 0.9202(14) 1 d PD A 1 C7 C 0.2043(3) 0.10303(9) 0.2020(3) 0.0223(4) Uani 0.9202(14) 1 d PD A 1 C8 C 0.2550(3) 0.01116(10) 0.3632(2) 0.0224(4) Uani 0.9202(14) 1 d PD A 1 C11 C 0.1899(3) 0.11502(9) 0.4965(2) 0.0243(4) Uani 0.9202(14) 1 d PD A 1 H11A H 0.1978 0.0837 0.5875 0.029 Uiso 0.9202(14) 1 calc PR A 1 C12 C 0.3493(3) 0.16374(11) 0.5505(3) 0.0261(6) Uani 0.9202(14) 1 d PD A 1 H12 H 0.4640 0.1582 0.5057 0.031 Uiso 0.9202(14) 1 calc PR A 1 C13 C 0.3097(4) 0.22942(11) 0.5980(3) 0.0284(5) Uani 0.9202(14) 1 d PD A 1 H13 H 0.4014 0.2637 0.5824 0.034 Uiso 0.9202(14) 1 calc PR A 1 C14 C 0.1083(3) 0.25171(9) 0.5868(2) 0.0253(4) Uani 0.9202(14) 1 d PD A 1 H14 H 0.0637 0.2742 0.4803 0.030 Uiso 0.9202(14) 1 calc PR A 1 C15 C -0.0260(3) 0.19532(9) 0.5872(3) 0.0255(5) Uani 0.9202(14) 1 d PD A 1 H15 H 0.0017 0.1747 0.6968 0.031 Uiso 0.9202(14) 1 calc PR A 1 C16 C -0.0094(3) 0.14568(10) 0.4604(3) 0.0270(6) Uani 0.9202(14) 1 d PD A 1 H16A H -0.0362 0.1668 0.3528 0.032 Uiso 0.9202(14) 1 calc PR A 1 H16B H -0.1058 0.1113 0.4568 0.032 Uiso 0.9202(14) 1 calc PR A 1 O1A O 0.157(2) 0.1539(7) 0.047(2) 0.0286(3) Uani 0.0798(14) 1 d PD A 2 O2A O 0.256(2) 0.0265(8) 0.5013(16) 0.0298(4) Uani 0.0798(14) 1 d PD A 2 O3A O 0.350(3) 0.2434(10) 0.573(3) 0.0311(4) Uani 0.0798(14) 1 d PD A 2 O4A O 0.081(3) 0.2759(8) 0.777(2) 0.0270(3) Uani 0.0798(14) 1 d PD A 2 H4A1 H 0.1508 0.2739 0.8717 0.040 Uiso 0.0798(14) 1 calc PR A 2 O5A O -0.218(3) 0.2090(17) 0.584(4) 0.0306(5) Uani 0.0798(14) 1 d PD A 2 H5A1 H -0.2594 0.2449 0.6075 0.046 Uiso 0.0798(14) 1 calc PR A 2 N1A N 0.212(3) 0.1039(8) 0.299(2) 0.0226(4) Uani 0.0798(14) 1 d PD A 2 C1A C 0.222(16) 0.0387(13) 0.084(3) 0.0233(7) Uani 0.0798(14) 1 d PD A 2 C2A C 0.224(4) 0.0142(12) -0.067(3) 0.0274(5) Uani 0.0798(14) 1 d PD A 2 H2A1 H 0.2008 0.0411 -0.1601 0.033 Uiso 0.0798(14) 1 calc PR A 2 C3A C 0.259(5) -0.0510(14) -0.075(3) 0.0304(5) Uani 0.0798(14) 1 d PD A 2 H3A1 H 0.2652 -0.0695 -0.1761 0.037 Uiso 0.0798(14) 1 calc PR A 2 C4A C 0.286(4) -0.0899(11) 0.059(3) 0.0297(5) Uani 0.0798(14) 1 d PD A 2 H4A2 H 0.3033 -0.1352 0.0485 0.036 Uiso 0.0798(14) 1 calc PR A 2 C5A C 0.290(4) -0.0646(10) 0.211(3) 0.0262(5) Uani 0.0798(14) 1 d PD A 2 H5A2 H 0.3175 -0.0914 0.3048 0.031 Uiso 0.0798(14) 1 calc PR A 2 C6A C 0.252(11) 0.0000(11) 0.223(3) 0.0226(5) Uani 0.0798(14) 1 d PD A 2 C7A C 0.196(4) 0.1063(8) 0.130(2) 0.0223(4) Uani 0.0798(14) 1 d PD A 2 C8A C 0.245(4) 0.0426(10) 0.3616(19) 0.0224(4) Uani 0.0798(14) 1 d PD A 2 C11A C 0.177(3) 0.1623(8) 0.389(2) 0.0243(4) Uani 0.0798(14) 1 d PD A 2 H11B H 0.1713 0.1997 0.3134 0.029 Uiso 0.0798(14) 1 calc PR A 2 C12A C 0.335(4) 0.1770(14) 0.535(3) 0.0261(6) Uani 0.0798(14) 1 d PD A 2 H12A H 0.4577 0.1531 0.5439 0.031 Uiso 0.0798(14) 1 calc PR A 2 C13A C 0.298(3) 0.2008(11) 0.689(2) 0.0284(5) Uani 0.0798(14) 1 d PD A 2 H13A H 0.3937 0.1915 0.7926 0.034 Uiso 0.0798(14) 1 calc PR A 2 C14A C 0.095(2) 0.2168(9) 0.695(2) 0.0253(4) Uani 0.0798(14) 1 d PD A 2 H14A H 0.0502 0.1813 0.7564 0.030 Uiso 0.0798(14) 1 calc PR A 2 C15A C -0.039(3) 0.2192(11) 0.531(2) 0.0255(5) Uani 0.0798(14) 1 d PD A 2 H15A H -0.0350 0.2610 0.4722 0.031 Uiso 0.0798(14) 1 calc PR A 2 C16A C -0.017(3) 0.1596(15) 0.432(4) 0.0270(6) Uani 0.0798(14) 1 d PD A 2 H16C H -0.1205 0.1582 0.3321 0.032 Uiso 0.0798(14) 1 calc PR A 2 H16D H -0.0250 0.1199 0.4957 0.032 Uiso 0.0798(14) 1 calc PR A 2 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 0.0284(7) 0.0214(7) 0.0366(8) 0.0082(6) 0.0088(6) 0.0013(5) O2 0.0407(8) 0.0234(7) 0.0263(8) 0.0045(6) 0.0098(6) 0.0025(6) O3 0.0322(8) 0.0327(8) 0.0250(7) -0.0052(6) 0.0006(6) 0.0071(6) O4 0.0317(8) 0.0201(7) 0.0264(8) -0.0027(6) 0.0020(7) 0.0000(6) O5 0.0244(7) 0.0261(11) 0.0424(14) -0.0107(9) 0.0102(8) 0.0002(6) N1 0.0254(8) 0.0204(9) 0.0223(9) 0.0000(7) 0.0061(7) 0.0015(7) C1 0.0188(16) 0.0259(11) 0.0245(11) 0.0017(9) 0.0038(14) -0.0004(17) C2 0.0226(10) 0.0341(12) 0.0243(10) 0.0045(9) 0.0034(8) 0.0003(10) C3 0.0252(10) 0.0453(14) 0.0203(10) -0.0048(10) 0.0046(9) 0.0007(10) C4 0.0245(11) 0.0320(12) 0.0315(14) -0.0104(10) 0.0049(11) 0.0019(9) C5 0.0236(10) 0.0257(10) 0.0278(12) -0.0017(10) 0.0035(10) 0.0020(8) C6 0.0183(12) 0.0254(11) 0.0235(11) -0.0003(9) 0.0039(12) 0.0005(10) C7 0.0175(9) 0.0239(10) 0.0246(12) 0.0032(9) 0.0035(10) -0.0010(7) C8 0.0217(9) 0.0199(10) 0.0250(10) 0.0009(8) 0.0045(8) 0.0002(9) C11 0.0294(10) 0.0208(9) 0.0239(10) -0.0003(7) 0.0090(8) 0.0003(7) C12 0.0229(10) 0.0289(13) 0.0254(10) -0.0025(9) 0.0035(8) 0.0013(9) C13 0.0341(13) 0.0250(12) 0.0276(12) -0.0019(9) 0.0104(9) -0.0097(9) C14 0.0289(10) 0.0201(9) 0.0260(10) -0.0014(8) 0.0044(8) -0.0020(8) C15 0.0240(10) 0.0199(10) 0.0328(12) -0.0022(8) 0.0075(9) 0.0000(8) C16 0.0221(9) 0.0234(13) 0.0358(14) -0.0061(10) 0.0074(9) -0.0036(8) O1A 0.0284(7) 0.0214(7) 0.0366(8) 0.0082(6) 0.0088(6) 0.0013(5) O2A 0.0407(8) 0.0234(7) 0.0263(8) 0.0045(6) 0.0098(6) 0.0025(6) O3A 0.0322(8) 0.0327(8) 0.0250(7) -0.0052(6) 0.0006(6) 0.0071(6) O4A 0.0317(8) 0.0201(7) 0.0264(8) -0.0027(6) 0.0020(7) 0.0000(6) O5A 0.0244(7) 0.0261(11) 0.0424(14) -0.0107(9) 0.0102(8) 0.0002(6) N1A 0.0254(8) 0.0204(9) 0.0223(9) 0.0000(7) 0.0061(7) 0.0015(7) C1A 0.0188(16) 0.0259(11) 0.0245(11) 0.0017(9) 0.0038(14) -0.0004(17) C2A 0.0226(10) 0.0341(12) 0.0243(10) 0.0045(9) 0.0034(8) 0.0003(10) C3A 0.0252(10) 0.0453(14) 0.0203(10) -0.0048(10) 0.0046(9) 0.0007(10) C4A 0.0245(11) 0.0320(12) 0.0315(14) -0.0104(10) 0.0049(11) 0.0019(9) C5A 0.0236(10) 0.0257(10) 0.0278(12) -0.0017(10) 0.0035(10) 0.0020(8) C6A 0.0183(12) 0.0254(11) 0.0235(11) -0.0003(9) 0.0039(12) 0.0005(10) C7A 0.0175(9) 0.0239(10) 0.0246(12) 0.0032(9) 0.0035(10) -0.0010(7) C8A 0.0217(9) 0.0199(10) 0.0250(10) 0.0009(8) 0.0045(8) 0.0002(9) C11A 0.0294(10) 0.0208(9) 0.0239(10) -0.0003(7) 0.0090(8) 0.0003(7) C12A 0.0229(10) 0.0289(13) 0.0254(10) -0.0025(9) 0.0035(8) 0.0013(9) C13A 0.0341(13) 0.0250(12) 0.0276(12) -0.0019(9) 0.0104(9) -0.0097(9) C14A 0.0289(10) 0.0201(9) 0.0260(10) -0.0014(8) 0.0044(8) -0.0020(8) C15A 0.0240(10) 0.0199(10) 0.0328(12) -0.0022(8) 0.0075(9) 0.0000(8) C16A 0.0221(9) 0.0234(13) 0.0358(14) -0.0061(10) 0.0074(9) -0.0036(8) _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 C7 1.213(2) . ? O2 C8 1.208(2) . ? O3 C13 1.433(3) . ? O3 C12 1.439(3) . ? O4 C14 1.424(2) . ? O4 H4O 0.79(3) . ? O5 C15 1.451(3) . ? O5 H5O 0.87(3) . ? N1 C7 1.398(3) . ? N1 C8 1.404(2) . ? N1 C11 1.465(2) . ? C1 C2 1.380(3) . ? C1 C6 1.386(3) . ? C1 C7 1.484(3) . ? C2 C3 1.389(3) . ? C2 H2A 0.9500 . ? C3 C4 1.389(3) . ? C3 H3A 0.9500 . ? C4 C5 1.394(3) . ? C4 H4A 0.9500 . ? C5 C6 1.385(3) . ? C5 H5A 0.9500 . ? C6 C8 1.481(3) . ? C11 C12 1.515(3) . ? C11 C16 1.535(3) . ? C11 H11A 1.0000 . ? C12 C13 1.462(3) . ? C12 H12 1.0000 . ? C13 C14 1.508(3) . ? C13 H13 1.0000 . ? C14 C15 1.516(3) . ? C14 H14 1.0000 . ? C15 C16 1.514(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O1A C7A 1.204(16) . ? O2A C8A 1.219(16) . ? O3A C12A 1.41(2) . ? O3A C13A 1.437(17) . ? O4A C14A 1.425(16) . ? O4A H4O 0.58(3) . ? O4A H4AA 0.8400 . ? O5A C15A 1.489(18) . ? O5A H5O 0.95(5) . ? O5A H5AA 0.8400 . ? N1A C8A 1.371(17) . ? N1A C7A 1.414(16) . ? N1A C11A 1.480(15) . ? C1A C2A 1.384(17) . ? C1A C6A 1.395(17) . ? C1A C7A 1.473(16) . ? C2A C3A 1.375(19) . ? C2A H2A1 0.9500 . ? C3A C4A 1.374(19) . ? C3A H3A1 0.9500 . ? C4A C5A 1.389(18) . ? C4A H4A2 0.9500 . ? C5A C6A 1.368(17) . ? C5A H5A2 0.9500 . ? C6A C8A 1.485(17) . ? C11A C12A 1.502(18) . ? C11A C16A 1.536(18) . ? C11A H11B 1.0000 . ? C12A C13A 1.482(18) . ? C12A H12A 1.0000 . ? C13A C14A 1.516(17) . ? C13A H13A 1.0000 . ? C14A C15A 1.493(17) . ? C14A H14A 1.0000 . ? C15A C16A 1.518(18) . ? C15A H15A 1.0000 . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O3 C12 61.22(13) . . ? C14 O4 H4O 109.5(16) . . ? C15 O5 H5O 108.2(19) . . ? C7 N1 C8 111.53(15) . . ? C7 N1 C11 125.45(19) . . ? C8 N1 C11 123.02(17) . . ? C2 C1 C6 121.7(2) . . ? C2 C1 C7 129.9(2) . . ? C6 C1 C7 108.4(2) . . ? C1 C2 C3 117.0(2) . . ? C1 C2 H2A 121.5 . . ? C3 C2 H2A 121.5 . . ? C2 C3 C4 121.65(19) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 117.0(2) . . ? C6 C5 H5A 121.5 . . ? C4 C5 H5A 121.5 . . ? C5 C6 C1 121.6(2) . . ? C5 C6 C8 130.2(2) . . ? C1 C6 C8 108.20(19) . . ? O1 C7 N1 124.6(2) . . ? O1 C7 C1 129.5(2) . . ? N1 C7 C1 105.89(17) . . ? O2 C8 N1 124.54(18) . . ? O2 C8 C6 129.48(19) . . ? N1 C8 C6 105.97(16) . . ? N1 C11 C12 110.88(16) . . ? N1 C11 C16 110.59(16) . . ? C12 C11 C16 113.30(16) . . ? N1 C11 H11A 107.3 . . ? C12 C11 H11A 107.3 . . ? C16 C11 H11A 107.3 . . ? O3 C12 C13 59.20(13) . . ? O3 C12 C11 114.0(2) . . ? C13 C12 C11 120.9(2) . . ? O3 C12 H12 116.6 . . ? C13 C12 H12 116.6 . . ? C11 C12 H12 116.6 . . ? O3 C13 C12 59.59(14) . . ? O3 C13 C14 116.34(17) . . ? C12 C13 C14 121.09(19) . . ? O3 C13 H13 116.0 . . ? C12 C13 H13 116.0 . . ? C14 C13 H13 116.0 . . ? O4 C14 C13 112.32(16) . . ? O4 C14 C15 111.06(16) . . ? C13 C14 C15 112.02(16) . . ? O4 C14 H14 107.0 . . ? C13 C14 H14 107.0 . . ? C15 C14 H14 107.0 . . ? O5 C15 C16 106.63(18) . . ? O5 C15 C14 108.76(18) . . ? C16 C15 C14 110.89(16) . . ? O5 C15 H15 110.2 . . ? C16 C15 H15 110.2 . . ? C14 C15 H15 110.2 . . ? C15 C16 C11 111.64(18) . . ? C15 C16 H16A 109.3 . . ? C11 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C11 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C12A O3A C13A 62.8(11) . . ? C14A O4A H4O 103(3) . . ? C14A O4A H4A1 109.5 . . ? H4O O4A H4A1 57.1 . . ? C15A O5A H5O 89(3) . . ? C15A O5A H5A1 109.5 . . ? H5O O5A H5A1 20.7 . . ? C8A N1A C7A 113.0(12) . . ? C8A N1A C11A 125.8(16) . . ? C7A N1A C11A 121.0(16) . . ? C2A C1A C6A 122.7(16) . . ? C2A C1A C7A 128.5(18) . . ? C6A C1A C7A 108.8(14) . . ? C3A C2A C1A 116.7(18) . . ? C3A C2A H2A1 121.6 . . ? C1A C2A H2A1 121.6 . . ? C4A C3A C2A 121(2) . . ? C4A C3A H3A1 119.4 . . ? C2A C3A H3A1 119.4 . . ? C3A C4A C5A 121.6(19) . . ? C3A C4A H4A2 119.2 . . ? C5A C4A H4A2 119.2 . . ? C6A C5A C4A 118.2(18) . . ? C6A C5A H5A2 120.9 . . ? C4A C5A H5A2 120.9 . . ? C5A C6A C1A 119.4(16) . . ? C5A C6A C8A 132.7(19) . . ? C1A C6A C8A 107.8(14) . . ? O1A C7A N1A 125.1(18) . . ? O1A C7A C1A 130.1(18) . . ? N1A C7A C1A 104.6(13) . . ? O2A C8A N1A 126.5(18) . . ? O2A C8A C6A 127.5(19) . . ? N1A C8A C6A 105.9(13) . . ? N1A C11A C12A 113.7(15) . . ? N1A C11A C16A 112.0(15) . . ? C12A C11A C16A 111.3(17) . . ? N1A C11A H11B 106.4 . . ? C12A C11A H11B 106.4 . . ? C16A C11A H11B 106.4 . . ? O3A C12A C13A 59.6(10) . . ? O3A C12A C11A 113(2) . . ? C13A C12A C11A 122.3(19) . . ? O3A C12A H12A 116.4 . . ? C13A C12A H12A 116.4 . . ? C11A C12A H12A 116.4 . . ? O3A C13A C12A 57.6(11) . . ? O3A C13A C14A 107.8(17) . . ? C12A C13A C14A 119.0(17) . . ? O3A C13A H13A 118.8 . . ? C12A C13A H13A 118.8 . . ? C14A C13A H13A 118.8 . . ? O4A C14A C15A 109.0(15) . . ? O4A C14A C13A 112.8(15) . . ? C15A C14A C13A 113.0(14) . . ? O4A C14A H14A 107.3 . . ? C15A C14A H14A 107.3 . . ? C13A C14A H14A 107.3 . . ? O5A C15A C14A 97.3(17) . . ? O5A C15A C16A 105.6(18) . . ? C14A C15A C16A 111.0(18) . . ? O5A C15A H15A 113.8 . . ? C14A C15A H15A 113.8 . . ? C16A C15A H15A 113.8 . . ? C15A C16A C11A 109.1(17) . . ? C15A C16A H16C 109.9 . . ? C11A C16A H16C 109.9 . . ? C15A C16A H16D 109.9 . . ? C11A C16A H16D 109.9 . . ? H16C C16A H16D 108.3 . . ? 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 C6 C1 C2 C3 0.8(9) . . . . ? C7 C1 C2 C3 -178.6(6) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C1 0.4(7) . . . . ? C4 C5 C6 C8 179.4(4) . . . . ? C2 C1 C6 C5 -0.8(10) . . . . ? C7 C1 C6 C5 178.7(4) . . . . ? C2 C1 C6 C8 180.0(5) . . . . ? C7 C1 C6 C8 -0.5(7) . . . . ? C8 N1 C7 O1 -178.84(19) . . . . ? C11 N1 C7 O1 1.5(3) . . . . ? C8 N1 C7 C1 1.5(4) . . . . ? C11 N1 C7 C1 -178.2(4) . . . . ? C2 C1 C7 O1 -0.7(10) . . . . ? C6 C1 C7 O1 179.8(4) . . . . ? C2 C1 C7 N1 178.9(6) . . . . ? C6 C1 C7 N1 -0.5(6) . . . . ? C7 N1 C8 O2 178.01(19) . . . . ? C11 N1 C8 O2 -2.3(3) . . . . ? C7 N1 C8 C6 -1.8(3) . . . . ? C11 N1 C8 C6 177.9(3) . . . . ? C5 C6 C8 O2 2.5(7) . . . . ? C1 C6 C8 O2 -178.4(4) . . . . ? C5 C6 C8 N1 -177.7(4) . . . . ? C1 C6 C8 N1 1.4(5) . . . . ? C7 N1 C11 C12 -66.8(2) . . . . ? C8 N1 C11 C12 113.54(19) . . . . ? C7 N1 C11 C16 59.8(2) . . . . ? C8 N1 C11 C16 -119.91(19) . . . . ? C13 O3 C12 C11 -112.9(2) . . . . ? N1 C11 C12 O3 -154.47(17) . . . . ? C16 C11 C12 O3 80.5(2) . . . . ? N1 C11 C12 C13 138.3(2) . . . . ? C16 C11 C12 C13 13.2(3) . . . . ? C12 O3 C13 C14 112.2(2) . . . . ? C11 C12 C13 O3 101.3(2) . . . . ? O3 C12 C13 C14 -104.3(2) . . . . ? C11 C12 C13 C14 -3.0(3) . . . . ? O3 C13 C14 O4 79.0(2) . . . . ? C12 C13 C14 O4 147.9(2) . . . . ? O3 C13 C14 C15 -46.8(2) . . . . ? C12 C13 C14 C15 22.1(3) . . . . ? O4 C14 C15 O5 64.9(2) . . . . ? C13 C14 C15 O5 -168.61(17) . . . . ? O4 C14 C15 C16 -178.16(16) . . . . ? C13 C14 C15 C16 -51.7(2) . . . . ? O5 C15 C16 C11 -178.09(17) . . . . ? C14 C15 C16 C11 63.7(2) . . . . ? N1 C11 C16 C15 -168.05(17) . . . . ? C12 C11 C16 C15 -42.9(2) . . . . ? C6A C1A C2A C3A -1(12) . . . . ? C7A C1A C2A C3A 178(8) . . . . ? C1A C2A C3A C4A 2(7) . . . . ? C2A C3A C4A C5A -4(5) . . . . ? C3A C4A C5A C6A 4(6) . . . . ? C4A C5A C6A C1A -4(9) . . . . ? C4A C5A C6A C8A -179(6) . . . . ? C2A C1A C6A C5A 2(14) . . . . ? C7A C1A C6A C5A -177(6) . . . . ? C2A C1A C6A C8A 179(8) . . . . ? C7A C1A C6A C8A 0(10) . . . . ? C8A N1A C7A O1A 176(2) . . . . ? C11A N1A C7A O1A 1(4) . . . . ? C8A N1A C7A C1A 0(6) . . . . ? C11A N1A C7A C1A -175(5) . . . . ? C2A C1A C7A O1A 6(14) . . . . ? C6A C1A C7A O1A -176(5) . . . . ? C2A C1A C7A N1A -179(9) . . . . ? C6A C1A C7A N1A 0(9) . . . . ? C7A N1A C8A O2A -176(3) . . . . ? C11A N1A C8A O2A -2(4) . . . . ? C7A N1A C8A C6A 0(4) . . . . ? C11A N1A C8A C6A 174(3) . . . . ? C5A C6A C8A O2A -8(10) . . . . ? C1A C6A C8A O2A 176(6) . . . . ? C5A C6A C8A N1A 176(7) . . . . ? C1A C6A C8A N1A 0(7) . . . . ? C8A N1A C11A C12A 58(3) . . . . ? C7A N1A C11A C12A -129(3) . . . . ? C8A N1A C11A C16A -70(3) . . . . ? C7A N1A C11A C16A 104(3) . . . . ? C13A O3A C12A C11A 115(2) . . . . ? N1A C11A C12A O3A 151.5(19) . . . . ? C16A C11A C12A O3A -81(3) . . . . ? N1A C11A C12A C13A -141(2) . . . . ? C16A C11A C12A C13A -13(3) . . . . ? C12A O3A C13A C14A -113.5(18) . . . . ? C11A C12A C13A O3A -99(3) . . . . ? O3A C12A C13A C14A 94(2) . . . . ? C11A C12A C13A C14A -6(3) . . . . ? O3A C13A C14A O4A -74(2) . . . . ? C12A C13A C14A O4A -136(2) . . . . ? O3A C13A C14A C15A 50(2) . . . . ? C12A C13A C14A C15A -12(3) . . . . ? O4A C14A C15A O5A -75(2) . . . . ? C13A C14A C15A O5A 159(2) . . . . ? O4A C14A C15A C16A 175.1(18) . . . . ? C13A C14A C15A C16A 49(2) . . . . ? O5A C15A C16A C11A -173(2) . . . . ? C14A C15A C16A C11A -69(3) . . . . ? N1A C11A C16A C15A 177(2) . . . . ? C12A C11A C16A C15A 49(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4O O5 0.79(3) 2.09(3) 2.852(3) 160(2) 4_666 O5 H5O O1 0.87(3) 2.05(3) 2.879(3) 160(3) 4_566 O5 H5O O4 0.87(3) 2.47(3) 2.885(3) 110(2) . O4A H4A1 O5A 0.84 1.86 2.68(4) 165.3 4_666 O5A H5A1 O1A 0.84 2.20 2.96(4) 150.9 4_566 O5A H5A1 O4A 0.84 2.61 2.75(4) 90.4 . _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 67.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.211 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.039