# 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_KAS29 _database_code_depnum_ccdc_archive 'CCDC 706778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H13 N O4' _chemical_formula_sum 'C10 H13 N O4' _chemical_formula_weight 211.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2977(16) _cell_length_b 6.6557(9) _cell_length_c 13.778(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.676(13) _cell_angle_gamma 90.00 _cell_volume 962.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3258 _cell_measurement_theta_min 4 _cell_measurement_theta_max 32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur"3 _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1827 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4738 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2154 _reflns_number_gt 1874 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'XP (Siemens, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0583P)^2^+0.1505P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2154 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 N1 N 0.22091(9) 0.47728(15) 0.18930(7) 0.0269(2) Uani 1 1 d . . . O1 O 0.04648(8) 0.27139(13) 0.11949(6) 0.0359(2) Uani 1 1 d . . . O2 O 0.41356(8) 0.61949(15) 0.28803(7) 0.0435(3) Uani 1 1 d . . . O3 O 0.07674(8) 0.43697(15) 0.33119(7) 0.0371(2) Uani 1 1 d . . . H3O H 0.0509(18) 0.536(3) 0.3583(14) 0.060(5) Uiso 1 1 d . . . O4 O 0.32526(9) 0.42670(17) 0.57609(7) 0.0435(3) Uani 1 1 d . . . H4O H 0.406(2) 0.427(3) 0.6111(15) 0.062(5) Uiso 1 1 d . . . C1 C 0.15167(10) 0.30234(17) 0.18585(8) 0.0267(2) Uani 1 1 d . . . C2 C 0.23267(11) 0.16305(17) 0.27135(8) 0.0283(3) Uani 1 1 d . . . H2 H 0.2432(14) 0.032(2) 0.2406(12) 0.043(4) Uiso 1 1 d . . . C3 C 0.19312(11) 0.12141(18) 0.36606(9) 0.0305(3) Uani 1 1 d . . . H3 H 0.1282(15) 0.014(3) 0.3526(12) 0.048(4) Uiso 1 1 d . . . C4 C 0.16485(10) 0.31848(19) 0.41175(8) 0.0286(3) Uani 1 1 d . . . H4 H 0.1314(14) 0.290(2) 0.4669(12) 0.038(4) Uiso 1 1 d . . . C5 C 0.29835(10) 0.41682(18) 0.46599(8) 0.0279(3) Uani 1 1 d . . . H5 H 0.2978(13) 0.555(2) 0.4366(11) 0.034(4) Uiso 1 1 d . . . C6 C 0.38763(10) 0.26999(17) 0.44045(8) 0.0275(2) Uani 1 1 d . . . H6 H 0.4790(14) 0.289(2) 0.4842(11) 0.036(4) Uiso 1 1 d . . . C7 C 0.32530(12) 0.06725(19) 0.44854(10) 0.0355(3) Uani 1 1 d . . . H7B H 0.3237(15) 0.042(2) 0.5212(12) 0.047(4) Uiso 1 1 d . . . H7A H 0.3664(16) -0.045(3) 0.4278(13) 0.050(4) Uiso 1 1 d . . . C8 C 0.36171(10) 0.27396(18) 0.32159(9) 0.0284(3) Uani 1 1 d . . . H8 H 0.4308(15) 0.207(2) 0.3051(12) 0.044(4) Uiso 1 1 d . . . C9 C 0.33988(10) 0.47646(18) 0.26801(8) 0.0284(2) Uani 1 1 d . . . C10 C 0.16645(13) 0.6502(2) 0.12283(10) 0.0356(3) Uani 1 1 d . . . H10C H 0.1094(16) 0.601(2) 0.0541(13) 0.051(5) Uiso 1 1 d . . . H10B H 0.1121(18) 0.727(3) 0.1517(14) 0.061(5) Uiso 1 1 d . . . H10A H 0.2372(17) 0.732(3) 0.1241(13) 0.051(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0251(4) 0.0309(5) 0.0229(4) 0.0011(4) 0.0069(4) -0.0017(4) O1 0.0331(4) 0.0426(5) 0.0252(4) -0.0018(3) 0.0029(3) -0.0099(4) O2 0.0323(5) 0.0527(6) 0.0385(5) 0.0073(4) 0.0049(4) -0.0162(4) O3 0.0294(4) 0.0502(6) 0.0272(4) -0.0005(4) 0.0051(3) 0.0147(4) O4 0.0322(5) 0.0717(7) 0.0237(4) -0.0093(4) 0.0069(4) 0.0004(4) C1 0.0282(5) 0.0311(5) 0.0208(5) -0.0037(4) 0.0090(4) -0.0026(4) C2 0.0306(6) 0.0264(5) 0.0261(5) -0.0020(4) 0.0083(4) 0.0012(4) C3 0.0299(6) 0.0297(6) 0.0284(5) 0.0047(4) 0.0066(4) -0.0035(4) C4 0.0217(5) 0.0419(6) 0.0214(5) 0.0032(4) 0.0070(4) 0.0019(4) C5 0.0254(5) 0.0344(6) 0.0227(5) -0.0012(4) 0.0072(4) 0.0008(4) C6 0.0200(5) 0.0357(6) 0.0239(5) 0.0045(4) 0.0047(4) 0.0039(4) C7 0.0352(6) 0.0330(6) 0.0337(6) 0.0092(5) 0.0074(5) 0.0059(5) C8 0.0231(5) 0.0370(6) 0.0261(5) 0.0012(4) 0.0103(4) 0.0057(4) C9 0.0235(5) 0.0392(6) 0.0237(5) 0.0004(4) 0.0101(4) -0.0020(4) C10 0.0335(6) 0.0342(6) 0.0336(6) 0.0052(5) 0.0060(5) -0.0004(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 N1 C9 1.3806(14) . ? N1 C1 1.3937(15) . ? N1 C10 1.4578(15) . ? O1 C1 1.2199(14) . ? O2 C9 1.2270(15) . ? O3 C4 1.4243(14) . ? O4 C5 1.4344(14) . ? C1 C2 1.5128(16) . ? C2 C8 1.5504(16) . ? C2 C3 1.5524(16) . ? C3 C4 1.5386(17) . ? C3 C7 1.5485(17) . ? C4 C5 1.5585(16) . ? C5 C6 1.5357(15) . ? C6 C7 1.5450(17) . ? C6 C8 1.5538(15) . ? C8 C9 1.5126(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 C9 N1 C1 113.25(9) . . ? C9 N1 C10 124.00(10) . . ? C1 N1 C10 122.46(10) . . ? O1 C1 N1 123.08(10) . . ? O1 C1 C2 128.45(11) . . ? N1 C1 C2 108.36(9) . . ? C1 C2 C8 104.74(9) . . ? C1 C2 C3 119.01(10) . . ? C8 C2 C3 102.99(9) . . ? C4 C3 C7 100.83(9) . . ? C4 C3 C2 111.07(9) . . ? C7 C3 C2 99.18(9) . . ? O3 C4 C3 110.13(9) . . ? O3 C4 C5 114.53(10) . . ? C3 C4 C5 104.11(9) . . ? O4 C5 C6 111.77(9) . . ? O4 C5 C4 108.42(9) . . ? C6 C5 C4 102.95(9) . . ? C5 C6 C7 100.59(9) . . ? C5 C6 C8 110.28(9) . . ? C7 C6 C8 100.22(9) . . ? C6 C7 C3 94.90(9) . . ? C9 C8 C2 104.44(9) . . ? C9 C8 C6 117.58(10) . . ? C2 C8 C6 104.04(9) . . ? O2 C9 N1 123.80(11) . . ? O2 C9 C8 127.36(10) . . ? N1 C9 C8 108.83(9) . . ? 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 C9 N1 C1 O1 -177.19(10) . . . . ? C10 N1 C1 O1 8.76(17) . . . . ? C9 N1 C1 C2 -0.72(12) . . . . ? C10 N1 C1 C2 -174.77(10) . . . . ? O1 C1 C2 C8 173.10(11) . . . . ? N1 C1 C2 C8 -3.13(11) . . . . ? O1 C1 C2 C3 -72.59(15) . . . . ? N1 C1 C2 C3 111.18(11) . . . . ? C1 C2 C3 C4 -49.01(13) . . . . ? C8 C2 C3 C4 66.24(11) . . . . ? C1 C2 C3 C7 -154.44(10) . . . . ? C8 C2 C3 C7 -39.19(11) . . . . ? C7 C3 C4 O3 156.10(9) . . . . ? C2 C3 C4 O3 51.76(12) . . . . ? C7 C3 C4 C5 32.87(11) . . . . ? C2 C3 C4 C5 -71.47(11) . . . . ? O3 C4 C5 O4 123.93(10) . . . . ? C3 C4 C5 O4 -115.76(10) . . . . ? O3 C4 C5 C6 -117.53(10) . . . . ? C3 C4 C5 C6 2.78(11) . . . . ? O4 C5 C6 C7 78.61(11) . . . . ? C4 C5 C6 C7 -37.55(10) . . . . ? O4 C5 C6 C8 -176.23(9) . . . . ? C4 C5 C6 C8 67.61(11) . . . . ? C5 C6 C7 C3 57.05(10) . . . . ? C8 C6 C7 C3 -56.03(10) . . . . ? C4 C3 C7 C6 -54.95(10) . . . . ? C2 C3 C7 C6 58.73(10) . . . . ? C1 C2 C8 C9 5.41(11) . . . . ? C3 C2 C8 C9 -119.71(9) . . . . ? C1 C2 C8 C6 129.27(9) . . . . ? C3 C2 C8 C6 4.15(11) . . . . ? C5 C6 C8 C9 41.98(13) . . . . ? C7 C6 C8 C9 147.39(10) . . . . ? C5 C6 C8 C2 -72.90(11) . . . . ? C7 C6 C8 C2 32.51(10) . . . . ? C1 N1 C9 O2 -176.21(11) . . . . ? C10 N1 C9 O2 -2.27(17) . . . . ? C1 N1 C9 C8 4.42(12) . . . . ? C10 N1 C9 C8 178.37(10) . . . . ? C2 C8 C9 O2 174.61(11) . . . . ? C6 C8 C9 O2 59.96(15) . . . . ? C2 C8 C9 N1 -6.05(11) . . . . ? C6 C8 C9 N1 -120.71(10) . . . . ? 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 O1 0.86(2) 2.00(2) 2.8377(13) 163.7(17) 2 O4 H4O O2 0.86(2) 2.03(2) 2.8680(14) 167.3(18) 3_666 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.239 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.036 data_KAS35 _database_code_depnum_ccdc_archive 'CCDC 706779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O4, C3 H8 O' _chemical_formula_sum 'C19 H25 N O5' _chemical_formula_weight 347.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 11.5561(15) _cell_length_b 11.7060(16) _cell_length_c 27.578(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3730.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23341 _cell_measurement_theta_min 3 _cell_measurement_theta_max 35 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur"3 _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1827 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29205 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.99 _reflns_number_total 5377 _reflns_number_gt 2335 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'XP (Siemens, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.1159P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5377 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1482 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _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 N1 N 0.49190(15) 0.26521(14) 0.64507(7) 0.0496(4) Uani 1 1 d . . . H1N H 0.4297 0.2762 0.6286 0.060 Uiso 1 1 calc R . . O1 O 0.45393(13) -0.01215(12) 0.77548(5) 0.0539(4) Uani 1 1 d . . . O2 O 0.46915(15) 0.15871(15) 0.80956(7) 0.0724(5) Uani 1 1 d . . . O3 O 0.39758(14) -0.16277(12) 0.66344(7) 0.0648(5) Uani 1 1 d . . . H3O H 0.4409 -0.2129 0.6735 0.097 Uiso 1 1 calc R . . O4 O 0.56448(13) 0.16829(13) 0.70956(6) 0.0643(5) Uani 1 1 d . . . C1 C 0.37510(18) -0.06607(17) 0.74158(8) 0.0496(5) Uani 1 1 d . . . H1 H 0.3581 -0.1450 0.7511 0.059 Uiso 1 1 calc R . . C2 C 0.41884(17) -0.05960(16) 0.68911(8) 0.0468(5) Uani 1 1 d . . . H2 H 0.5006 -0.0378 0.6877 0.056 Uiso 1 1 calc R . . C3 C 0.34127(17) 0.03157(16) 0.66678(9) 0.0489(5) Uani 1 1 d . . . H3 H 0.3423 0.0342 0.6313 0.059 Uiso 1 1 calc R . . C4 C 0.36185(16) 0.14792(16) 0.69198(9) 0.0480(5) Uani 1 1 d . . . H4 H 0.3066 0.2028 0.6784 0.058 Uiso 1 1 calc R . . C5 C 0.32653(18) 0.12452(18) 0.74549(9) 0.0531(6) Uani 1 1 d . . . H5 H 0.2751 0.1837 0.7584 0.064 Uiso 1 1 calc R . . C6 C 0.26531(17) 0.00710(18) 0.74107(9) 0.0542(6) Uani 1 1 d . . . H6 H 0.2078 -0.0104 0.7661 0.065 Uiso 1 1 calc R . . C7 C 0.22338(17) 0.0003(2) 0.68914(10) 0.0584(6) Uani 1 1 d . . . H7B H 0.1637 0.0560 0.6819 0.070 Uiso 1 1 calc R . . H7A H 0.1977 -0.0757 0.6802 0.070 Uiso 1 1 calc R . . C8 C 0.42511(19) 0.09788(19) 0.77946(9) 0.0539(6) Uani 1 1 d . . . C9 C 0.48283(17) 0.19479(17) 0.68374(8) 0.0464(5) Uani 1 1 d . . . C10 C 0.59260(18) 0.32318(17) 0.62860(8) 0.0484(5) Uani 1 1 d . . . C11 C 0.5787(2) 0.4253(2) 0.60448(10) 0.0652(6) Uani 1 1 d . . . H11 H 0.5049 0.4551 0.5999 0.078 Uiso 1 1 calc R . . C12 C 0.6739(2) 0.4837(2) 0.58710(11) 0.0749(8) Uani 1 1 d . . . H12 H 0.6630 0.5525 0.5708 0.090 Uiso 1 1 calc R . . C13 C 0.7849(2) 0.4422(2) 0.59330(10) 0.0647(7) Uani 1 1 d . . . C14 C 0.7968(2) 0.3405(2) 0.61728(9) 0.0659(7) Uani 1 1 d . . . H14 H 0.8708 0.3111 0.6219 0.079 Uiso 1 1 calc R . . C15 C 0.7032(2) 0.2798(2) 0.63499(9) 0.0589(6) Uani 1 1 d . . . H15 H 0.7143 0.2107 0.6510 0.071 Uiso 1 1 calc R . . C16 C 0.8883(3) 0.5061(3) 0.57348(13) 0.0946(10) Uani 1 1 d . . . H16C H 0.8807 0.5141 0.5390 0.142 Uiso 1 1 calc R . . H16B H 0.9577 0.4644 0.5808 0.142 Uiso 1 1 calc R . . H16A H 0.8923 0.5804 0.5881 0.142 Uiso 1 1 calc R . . O1S O 0.27189(15) 0.3026(2) 0.59367(7) 0.0856(6) Uani 1 1 d . . . H1SA H 0.2144 0.3131 0.6105 0.128 Uiso 1 1 calc R . . C1S C 0.2379(4) 0.2671(4) 0.54755(13) 0.1169(13) Uani 1 1 d . . . H1S H 0.2024 0.3348 0.5329 0.140 Uiso 1 1 calc R . . C2S C 0.1478(5) 0.1827(7) 0.5476(2) 0.240(4) Uani 1 1 d . . . H2SC H 0.1812 0.1082 0.5513 0.361 Uiso 1 1 calc R . . H2SB H 0.1061 0.1863 0.5175 0.361 Uiso 1 1 calc R . . H2SA H 0.0957 0.1973 0.5740 0.361 Uiso 1 1 calc R . . C3S C 0.3435(5) 0.2480(6) 0.51931(16) 0.187(3) Uani 1 1 d . . . H3SA H 0.3969 0.3094 0.5251 0.281 Uiso 1 1 calc R . . H3SB H 0.3246 0.2452 0.4854 0.281 Uiso 1 1 calc R . . H3SC H 0.3782 0.1770 0.5289 0.281 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0407(9) 0.0503(10) 0.0579(11) 0.0041(9) -0.0030(8) 0.0021(8) O1 0.0497(8) 0.0511(9) 0.0609(9) 0.0011(7) -0.0071(7) -0.0035(7) O2 0.0616(11) 0.0729(11) 0.0827(12) -0.0211(10) 0.0016(9) -0.0148(9) O3 0.0574(10) 0.0482(8) 0.0888(13) -0.0128(8) -0.0195(9) 0.0104(7) O4 0.0394(8) 0.0678(10) 0.0857(12) 0.0268(8) -0.0084(8) -0.0054(7) C1 0.0425(10) 0.0382(10) 0.0680(15) 0.0021(10) -0.0040(10) -0.0075(8) C2 0.0351(10) 0.0392(10) 0.0660(14) -0.0028(10) -0.0053(10) 0.0022(8) C3 0.0382(10) 0.0466(11) 0.0619(14) 0.0023(10) -0.0076(10) -0.0006(9) C4 0.0311(9) 0.0378(10) 0.0750(15) 0.0074(10) -0.0025(10) 0.0029(8) C5 0.0416(11) 0.0452(11) 0.0724(15) -0.0057(11) 0.0119(11) 0.0030(9) C6 0.0343(10) 0.0503(12) 0.0779(17) 0.0020(11) 0.0078(10) -0.0070(9) C7 0.0347(10) 0.0526(12) 0.0877(18) 0.0036(12) -0.0082(11) -0.0011(9) C8 0.0444(12) 0.0513(13) 0.0659(14) -0.0019(11) 0.0114(11) -0.0079(10) C9 0.0383(11) 0.0375(9) 0.0635(13) 0.0013(10) 0.0016(10) -0.0001(8) C10 0.0450(11) 0.0521(12) 0.0482(12) -0.0018(10) 0.0051(9) 0.0014(10) C11 0.0587(14) 0.0582(14) 0.0786(16) 0.0125(12) 0.0089(13) 0.0056(11) C12 0.0792(19) 0.0543(14) 0.091(2) 0.0154(13) 0.0142(16) -0.0026(14) C13 0.0619(15) 0.0708(16) 0.0613(15) -0.0079(13) 0.0088(12) -0.0192(13) C14 0.0466(13) 0.0909(19) 0.0601(15) 0.0029(14) 0.0023(11) -0.0068(13) C15 0.0523(13) 0.0632(14) 0.0612(15) 0.0064(12) 0.0004(11) -0.0016(11) C16 0.082(2) 0.103(2) 0.099(2) 0.0038(19) 0.0168(17) -0.0384(18) O1S 0.0594(11) 0.1380(17) 0.0595(11) -0.0157(12) -0.0020(9) 0.0124(12) C1S 0.116(3) 0.161(4) 0.074(2) -0.023(2) -0.014(2) 0.010(3) C2S 0.141(5) 0.373(11) 0.207(7) -0.140(7) -0.021(4) -0.073(6) C3S 0.190(5) 0.290(8) 0.083(3) -0.054(4) 0.031(3) 0.004(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 N1 C9 1.352(3) . ? N1 C10 1.422(3) . ? O1 C8 1.335(3) . ? O1 C1 1.450(3) . ? O2 C8 1.206(3) . ? O3 C2 1.421(2) . ? O4 C9 1.222(2) . ? C1 C6 1.531(3) . ? C1 C2 1.535(3) . ? C2 C3 1.524(3) . ? C3 C7 1.539(3) . ? C3 C4 1.547(3) . ? C4 C9 1.519(3) . ? C4 C5 1.555(3) . ? C5 C8 1.508(3) . ? C5 C6 1.551(3) . ? C6 C7 1.514(4) . ? C10 C11 1.378(3) . ? C10 C15 1.386(3) . ? C11 C12 1.381(3) . ? C12 C13 1.382(4) . ? C13 C14 1.369(4) . ? C13 C16 1.512(3) . ? C14 C15 1.384(3) . ? O1S C1S 1.394(4) . ? C1S C2S 1.436(7) . ? C1S C3S 1.464(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C10 127.35(18) . . ? C8 O1 C1 108.44(16) . . ? O1 C1 C6 106.44(16) . . ? O1 C1 C2 112.31(16) . . ? C6 C1 C2 103.69(17) . . ? O3 C2 C3 106.99(16) . . ? O3 C2 C1 111.76(17) . . ? C3 C2 C1 102.82(16) . . ? C2 C3 C7 101.09(17) . . ? C2 C3 C4 110.15(17) . . ? C7 C3 C4 99.52(17) . . ? C9 C4 C3 113.10(17) . . ? C9 C4 C5 116.56(18) . . ? C3 C4 C5 103.34(16) . . ? C8 C5 C6 102.14(18) . . ? C8 C5 C4 115.32(17) . . ? C6 C5 C4 101.61(18) . . ? C7 C6 C1 104.16(19) . . ? C7 C6 C5 105.48(19) . . ? C1 C6 C5 96.73(15) . . ? C6 C7 C3 94.77(16) . . ? O2 C8 O1 121.4(2) . . ? O2 C8 C5 128.6(2) . . ? O1 C8 C5 109.70(19) . . ? O4 C9 N1 123.67(18) . . ? O4 C9 C4 122.12(19) . . ? N1 C9 C4 114.18(18) . . ? C11 C10 C15 119.2(2) . . ? C11 C10 N1 118.22(19) . . ? C15 C10 N1 122.61(19) . . ? C10 C11 C12 120.3(2) . . ? C11 C12 C13 121.5(2) . . ? C14 C13 C12 117.3(2) . . ? C14 C13 C16 121.6(3) . . ? C12 C13 C16 121.0(3) . . ? C13 C14 C15 122.6(2) . . ? C14 C15 C10 119.2(2) . . ? O1S C1S C2S 114.1(4) . . ? O1S C1S C3S 107.2(3) . . ? C2S C1S C3S 120.0(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 C8 O1 C1 C6 -23.3(2) . . . . ? C8 O1 C1 C2 89.47(19) . . . . ? O1 C1 C2 O3 140.08(16) . . . . ? C6 C1 C2 O3 -105.42(17) . . . . ? O1 C1 C2 C3 -105.50(18) . . . . ? C6 C1 C2 C3 9.01(19) . . . . ? O3 C2 C3 C7 77.0(2) . . . . ? C1 C2 C3 C7 -40.9(2) . . . . ? O3 C2 C3 C4 -178.47(17) . . . . ? C1 C2 C3 C4 63.7(2) . . . . ? C2 C3 C4 C9 65.1(2) . . . . ? C7 C3 C4 C9 170.75(18) . . . . ? C2 C3 C4 C5 -61.8(2) . . . . ? C7 C3 C4 C5 43.83(19) . . . . ? C9 C4 C5 C8 -27.2(2) . . . . ? C3 C4 C5 C8 97.48(19) . . . . ? C9 C4 C5 C6 -136.77(17) . . . . ? C3 C4 C5 C6 -12.07(19) . . . . ? O1 C1 C6 C7 145.30(17) . . . . ? C2 C1 C6 C7 26.67(19) . . . . ? O1 C1 C6 C5 37.4(2) . . . . ? C2 C1 C6 C5 -81.20(18) . . . . ? C8 C5 C6 C7 -144.04(18) . . . . ? C4 C5 C6 C7 -24.7(2) . . . . ? C8 C5 C6 C1 -37.3(2) . . . . ? C4 C5 C6 C1 82.09(18) . . . . ? C1 C6 C7 C3 -50.31(19) . . . . ? C5 C6 C7 C3 50.94(19) . . . . ? C2 C3 C7 C6 55.79(19) . . . . ? C4 C3 C7 C6 -57.09(18) . . . . ? C1 O1 C8 O2 171.5(2) . . . . ? C1 O1 C8 C5 -2.9(2) . . . . ? C6 C5 C8 O2 -146.7(2) . . . . ? C4 C5 C8 O2 104.0(3) . . . . ? C6 C5 C8 O1 27.2(2) . . . . ? C4 C5 C8 O1 -82.1(2) . . . . ? C10 N1 C9 O4 -2.5(3) . . . . ? C10 N1 C9 C4 179.06(18) . . . . ? C3 C4 C9 O4 -86.2(3) . . . . ? C5 C4 C9 O4 33.4(3) . . . . ? C3 C4 C9 N1 92.3(2) . . . . ? C5 C4 C9 N1 -148.12(18) . . . . ? C9 N1 C10 C11 -151.2(2) . . . . ? C9 N1 C10 C15 30.1(3) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? N1 C10 C11 C12 -178.9(2) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? C11 C12 C13 C16 179.1(3) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C16 C13 C14 C15 -178.9(3) . . . . ? C13 C14 C15 C10 -0.3(4) . . . . ? C11 C10 C15 C14 0.4(4) . . . . ? N1 C10 C15 C14 179.1(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 O3 H3O O2 0.82 1.89 2.701(2) 172.2 3_646 N1 H1N O1S 0.86 2.09 2.944(2) 175.5 . O1S H1SA O3 0.82 1.97 2.775(2) 166.7 8_665 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.310 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.056 data_KAS36 _database_code_depnum_ccdc_archive 'CCDC 706780' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N2 O6' _chemical_formula_sum 'C15 H14 N2 O6' _chemical_formula_weight 318.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2192(13) _cell_length_b 9.064(2) _cell_length_c 11.0633(16) _cell_angle_alpha 73.995(18) _cell_angle_beta 80.033(14) _cell_angle_gamma 73.38(2) _cell_volume 663.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3284 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur"3 _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1827 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4797 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2960 _reflns_number_gt 2473 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'XP (Siemens, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0580P)^2^+0.0903P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2960 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 N1 N 0.34016(14) 0.16369(12) 0.35544(9) 0.0123(2) Uani 1 1 d . . . N2 N -0.20001(16) 0.25881(13) 0.67829(10) 0.0181(2) Uani 1 1 d . . . O1 O 0.07556(12) 0.12872(10) 0.28468(8) 0.0160(2) Uani 1 1 d . . . O2 O 0.72450(13) 0.36597(11) 0.22457(8) 0.0169(2) Uani 1 1 d . . . H2O H 0.828(3) 0.286(3) 0.240(2) 0.047(6) Uiso 1 1 d . . . O3 O 0.18293(13) 0.45125(10) 0.08681(8) 0.0170(2) Uani 1 1 d . . . O4 O 0.12991(14) 0.31271(11) -0.03603(9) 0.0208(2) Uani 1 1 d . . . H4O H 0.027(3) 0.390(3) -0.0458(18) 0.039(5) Uiso 1 1 d . . . O5 O -0.29897(13) 0.21543(12) 0.62252(9) 0.0222(2) Uani 1 1 d . . . O6 O -0.24954(17) 0.28351(15) 0.78376(10) 0.0350(3) Uani 1 1 d . . . C1 C 0.54419(17) 0.15667(14) 0.30645(11) 0.0128(2) Uani 1 1 d . . . H1 H 0.625(2) 0.1291(18) 0.3773(14) 0.017(4) Uiso 1 1 d . . . C2 C 0.56792(17) 0.31097(14) 0.20624(11) 0.0132(2) Uani 1 1 d . . . H2 H 0.452(2) 0.3952(16) 0.2145(12) 0.007(3) Uiso 1 1 d . . . C3 C 0.60113(17) 0.25902(14) 0.08149(11) 0.0137(2) Uani 1 1 d . . . H3 H 0.646(2) 0.3324(19) 0.0121(14) 0.016(4) Uiso 1 1 d . . . C4 C 0.42212(17) 0.21433(14) 0.05746(11) 0.0132(2) Uani 1 1 d . . . H4 H 0.454(2) 0.1734(18) -0.0172(14) 0.012(3) Uiso 1 1 d . . . C5 C 0.40091(17) 0.07095(14) 0.17330(11) 0.0126(2) Uani 1 1 d . . . H5 H 0.371(2) -0.0153(18) 0.1488(14) 0.015(3) Uiso 1 1 d . . . C6 C 0.59659(17) 0.03091(14) 0.22842(11) 0.0138(2) Uani 1 1 d . . . H6 H 0.635(2) -0.0756(18) 0.2760(14) 0.014(3) Uiso 1 1 d . . . C7 C 0.73637(18) 0.09239(15) 0.11822(12) 0.0158(2) Uani 1 1 d . . . H7B H 0.764(2) 0.0344(17) 0.0493(13) 0.012(3) Uiso 1 1 d . . . H7A H 0.859(2) 0.0932(19) 0.1450(14) 0.018(4) Uiso 1 1 d . . . C8 C 0.23440(17) 0.33975(14) 0.03751(11) 0.0141(2) Uani 1 1 d . . . C9 C 0.24881(17) 0.12198(14) 0.27621(11) 0.0124(2) Uani 1 1 d . . . C10 C 0.24729(17) 0.23650(14) 0.45433(11) 0.0126(2) Uani 1 1 d . . . C11 C 0.06998(17) 0.21112(14) 0.51712(11) 0.0136(2) Uani 1 1 d . . . H11 H 0.008(2) 0.1459(18) 0.4941(14) 0.014(3) Uiso 1 1 d . . . C12 C -0.01137(17) 0.28371(14) 0.61483(11) 0.0149(2) Uani 1 1 d . . . C13 C 0.07230(19) 0.37857(15) 0.65474(11) 0.0162(3) Uani 1 1 d . . . H13 H 0.010(2) 0.427(2) 0.7214(16) 0.025(4) Uiso 1 1 d . . . C14 C 0.24885(19) 0.40215(15) 0.59111(11) 0.0163(3) Uani 1 1 d . . . H14 H 0.309(2) 0.4677(19) 0.6161(15) 0.021(4) Uiso 1 1 d . . . C15 C 0.33545(18) 0.33298(14) 0.49163(11) 0.0145(2) Uani 1 1 d . . . H15 H 0.462(2) 0.3488(18) 0.4468(14) 0.019(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 N1 0.0107(5) 0.0150(5) 0.0122(5) -0.0049(4) -0.0008(4) -0.0034(4) N2 0.0173(5) 0.0163(5) 0.0176(5) -0.0037(4) 0.0024(4) -0.0025(4) O1 0.0117(4) 0.0206(5) 0.0178(4) -0.0070(3) -0.0020(3) -0.0045(3) O2 0.0135(4) 0.0188(5) 0.0219(5) -0.0073(3) -0.0031(3) -0.0062(4) O3 0.0169(4) 0.0168(4) 0.0183(4) -0.0069(3) -0.0056(3) -0.0009(3) O4 0.0199(5) 0.0190(5) 0.0255(5) -0.0095(4) -0.0120(4) 0.0014(4) O5 0.0153(4) 0.0279(5) 0.0214(5) -0.0016(4) -0.0023(4) -0.0063(4) O6 0.0394(6) 0.0464(7) 0.0262(5) -0.0214(5) 0.0175(5) -0.0217(5) C1 0.0100(5) 0.0160(6) 0.0126(5) -0.0047(4) -0.0017(4) -0.0022(4) C2 0.0113(5) 0.0148(6) 0.0151(6) -0.0056(4) -0.0021(4) -0.0034(4) C3 0.0122(5) 0.0160(6) 0.0134(6) -0.0043(4) -0.0007(4) -0.0040(5) C4 0.0140(5) 0.0148(6) 0.0119(5) -0.0052(4) -0.0019(4) -0.0032(4) C5 0.0122(5) 0.0125(5) 0.0139(5) -0.0050(4) -0.0025(4) -0.0020(4) C6 0.0128(5) 0.0132(6) 0.0153(6) -0.0047(4) -0.0036(4) -0.0007(4) C7 0.0115(5) 0.0183(6) 0.0181(6) -0.0078(5) -0.0009(4) -0.0018(5) C8 0.0148(6) 0.0154(6) 0.0116(5) -0.0006(4) -0.0025(4) -0.0050(5) C9 0.0139(5) 0.0112(5) 0.0119(5) -0.0016(4) -0.0023(4) -0.0032(4) C10 0.0139(5) 0.0126(5) 0.0102(5) -0.0019(4) -0.0030(4) -0.0016(4) C11 0.0145(6) 0.0128(5) 0.0135(5) -0.0023(4) -0.0030(4) -0.0032(4) C12 0.0144(6) 0.0140(6) 0.0130(5) -0.0010(4) -0.0006(4) -0.0012(5) C13 0.0208(6) 0.0146(6) 0.0112(5) -0.0041(4) -0.0018(5) -0.0005(5) C14 0.0198(6) 0.0156(6) 0.0156(6) -0.0050(4) -0.0053(5) -0.0046(5) C15 0.0142(5) 0.0151(6) 0.0146(6) -0.0028(4) -0.0032(4) -0.0040(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.3681(15) . ? N1 C10 1.4047(15) . ? N1 C1 1.4684(15) . ? N2 O5 1.2217(15) . ? N2 O6 1.2221(15) . ? N2 C12 1.4683(16) . ? O1 C9 1.2230(15) . ? O2 C2 1.4230(14) . ? O2 H2O 0.88(2) . ? O3 C8 1.2149(16) . ? O4 C8 1.3112(14) . ? O4 H4O 0.86(2) . ? C1 C6 1.5397(17) . ? C1 C2 1.5590(17) . ? C1 H1 0.993(15) . ? C2 C3 1.5374(17) . ? C2 H2 0.970(14) . ? C3 C7 1.5345(17) . ? C3 C4 1.5435(16) . ? C3 H3 0.945(16) . ? C4 C8 1.5038(17) . ? C4 C5 1.5756(17) . ? C4 H4 0.963(15) . ? C5 C9 1.5109(17) . ? C5 C6 1.5434(16) . ? C5 H5 0.981(15) . ? C6 C7 1.5285(18) . ? C6 H6 0.950(15) . ? C7 H7B 1.003(14) . ? C7 H7A 0.982(15) . ? C10 C11 1.3952(17) . ? C10 C15 1.3958(17) . ? C11 C12 1.3776(17) . ? C11 H11 0.941(15) . ? C12 C13 1.3776(18) . ? C13 C14 1.3885(18) . ? C13 H13 0.944(17) . ? C14 C15 1.3832(18) . ? C14 H14 0.949(16) . ? C15 H15 0.993(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 C9 N1 C10 125.46(10) . . ? C9 N1 C1 110.68(9) . . ? C10 N1 C1 122.50(9) . . ? O5 N2 O6 123.71(11) . . ? O5 N2 C12 118.24(10) . . ? O6 N2 C12 118.05(11) . . ? C2 O2 H2O 110.0(14) . . ? C8 O4 H4O 107.8(13) . . ? N1 C1 C6 103.83(9) . . ? N1 C1 C2 112.12(9) . . ? C6 C1 C2 103.48(9) . . ? N1 C1 H1 110.3(9) . . ? C6 C1 H1 113.6(9) . . ? C2 C1 H1 113.1(9) . . ? O2 C2 C3 112.56(10) . . ? O2 C2 C1 112.74(9) . . ? C3 C2 C1 102.29(9) . . ? O2 C2 H2 106.0(8) . . ? C3 C2 H2 114.5(8) . . ? C1 C2 H2 108.9(8) . . ? C7 C3 C2 101.12(9) . . ? C7 C3 C4 99.31(10) . . ? C2 C3 C4 111.78(10) . . ? C7 C3 H3 117.4(10) . . ? C2 C3 H3 112.8(9) . . ? C4 C3 H3 113.2(9) . . ? C8 C4 C3 119.40(10) . . ? C8 C4 C5 112.66(10) . . ? C3 C4 C5 103.18(9) . . ? C8 C4 H4 105.5(9) . . ? C3 C4 H4 108.5(9) . . ? C5 C4 H4 107.0(9) . . ? C9 C5 C6 104.85(9) . . ? C9 C5 C4 112.10(10) . . ? C6 C5 C4 101.34(9) . . ? C9 C5 H5 109.2(9) . . ? C6 C5 H5 116.3(9) . . ? C4 C5 H5 112.7(9) . . ? C7 C6 C1 103.52(10) . . ? C7 C6 C5 105.35(9) . . ? C1 C6 C5 98.58(9) . . ? C7 C6 H6 118.6(9) . . ? C1 C6 H6 114.8(9) . . ? C5 C6 H6 113.6(9) . . ? C6 C7 C3 94.82(9) . . ? C6 C7 H7B 113.2(8) . . ? C3 C7 H7B 112.6(8) . . ? C6 C7 H7A 113.0(9) . . ? C3 C7 H7A 112.7(9) . . ? H7B C7 H7A 109.8(13) . . ? O3 C8 O4 123.78(11) . . ? O3 C8 C4 123.76(11) . . ? O4 C8 C4 112.43(11) . . ? O1 C9 N1 126.61(11) . . ? O1 C9 C5 126.17(11) . . ? N1 C9 C5 107.19(10) . . ? C11 C10 C15 119.70(11) . . ? C11 C10 N1 120.78(10) . . ? C15 C10 N1 119.51(11) . . ? C12 C11 C10 117.80(11) . . ? C12 C11 H11 121.0(9) . . ? C10 C11 H11 121.2(9) . . ? C11 C12 C13 124.03(11) . . ? C11 C12 N2 117.24(11) . . ? C13 C12 N2 118.73(11) . . ? C12 C13 C14 117.26(11) . . ? C12 C13 H13 120.9(10) . . ? C14 C13 H13 121.8(10) . . ? C15 C14 C13 120.85(11) . . ? C15 C14 H14 120.0(10) . . ? C13 C14 H14 119.1(10) . . ? C14 C15 C10 120.35(11) . . ? C14 C15 H15 120.9(9) . . ? C10 C15 H15 118.8(9) . . ? 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 C9 N1 C1 C6 -27.55(12) . . . . ? C10 N1 C1 C6 165.11(10) . . . . ? C9 N1 C1 C2 83.49(12) . . . . ? C10 N1 C1 C2 -83.84(13) . . . . ? N1 C1 C2 O2 135.63(10) . . . . ? C6 C1 C2 O2 -113.10(10) . . . . ? N1 C1 C2 C3 -103.23(10) . . . . ? C6 C1 C2 C3 8.04(11) . . . . ? O2 C2 C3 C7 80.38(11) . . . . ? C1 C2 C3 C7 -40.88(11) . . . . ? O2 C2 C3 C4 -174.78(9) . . . . ? C1 C2 C3 C4 63.96(11) . . . . ? C7 C3 C4 C8 170.51(10) . . . . ? C2 C3 C4 C8 64.49(14) . . . . ? C7 C3 C4 C5 44.63(11) . . . . ? C2 C3 C4 C5 -61.38(12) . . . . ? C8 C4 C5 C9 -31.34(13) . . . . ? C3 C4 C5 C9 98.75(11) . . . . ? C8 C4 C5 C6 -142.66(10) . . . . ? C3 C4 C5 C6 -12.56(11) . . . . ? N1 C1 C6 C7 144.97(9) . . . . ? C2 C1 C6 C7 27.73(11) . . . . ? N1 C1 C6 C5 36.82(11) . . . . ? C2 C1 C6 C5 -80.43(10) . . . . ? C9 C5 C6 C7 -141.01(10) . . . . ? C4 C5 C6 C7 -24.26(11) . . . . ? C9 C5 C6 C1 -34.35(11) . . . . ? C4 C5 C6 C1 82.40(10) . . . . ? C1 C6 C7 C3 -51.75(10) . . . . ? C5 C6 C7 C3 51.27(11) . . . . ? C2 C3 C7 C6 56.83(10) . . . . ? C4 C3 C7 C6 -57.72(10) . . . . ? C3 C4 C8 O3 -31.67(17) . . . . ? C5 C4 C8 O3 89.58(14) . . . . ? C3 C4 C8 O4 150.23(11) . . . . ? C5 C4 C8 O4 -88.52(12) . . . . ? C10 N1 C9 O1 -6.53(19) . . . . ? C1 N1 C9 O1 -173.41(11) . . . . ? C10 N1 C9 C5 171.62(10) . . . . ? C1 N1 C9 C5 4.74(12) . . . . ? C6 C5 C9 O1 -161.91(11) . . . . ? C4 C5 C9 O1 89.00(14) . . . . ? C6 C5 C9 N1 19.93(12) . . . . ? C4 C5 C9 N1 -89.16(11) . . . . ? C9 N1 C10 C11 28.93(17) . . . . ? C1 N1 C10 C11 -165.65(11) . . . . ? C9 N1 C10 C15 -152.27(11) . . . . ? C1 N1 C10 C15 13.14(16) . . . . ? C15 C10 C11 C12 -0.02(17) . . . . ? N1 C10 C11 C12 178.77(10) . . . . ? C10 C11 C12 C13 -0.50(18) . . . . ? C10 C11 C12 N2 178.70(10) . . . . ? O5 N2 C12 C11 -19.98(16) . . . . ? O6 N2 C12 C11 160.39(12) . . . . ? O5 N2 C12 C13 159.27(11) . . . . ? O6 N2 C12 C13 -20.36(17) . . . . ? C11 C12 C13 C14 0.42(18) . . . . ? N2 C12 C13 C14 -178.77(10) . . . . ? C12 C13 C14 C15 0.19(18) . . . . ? C13 C14 C15 C10 -0.69(18) . . . . ? C11 C10 C15 C14 0.61(17) . . . . ? N1 C10 C15 C14 -178.21(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.88(2) 1.99(2) 2.8578(15) 171(2) 1_655 O4 H4O O3 0.86(2) 1.79(2) 2.6469(15) 172.6(19) 2_565 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.365 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.048