# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_w1 _database_code_depnum_ccdc_archive 'CCDC 818047' #TrackingRef 'W1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C11 H12 N2 O6' _chemical_formula_sum 'C11 H12 N2 O6' _chemical_formula_weight 268.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5043(18) _cell_length_b 20.894(5) _cell_length_c 7.5043(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.58 _cell_angle_gamma 90.00 _cell_volume 1176.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6464 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2319 _reflns_number_gt 2055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.2946P] 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 2319 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 O6 O 0.32469(14) 0.63992(5) 0.30874(15) 0.0415(3) Uani 1 1 d . . . C1 C 0.11096(18) 0.70542(6) 0.45158(17) 0.0289(3) Uani 1 1 d . . . N2 N 0.22209(17) 0.87841(6) 0.41956(17) 0.0404(3) Uani 1 1 d . . . O5 O 0.12817(16) 0.59261(5) 0.48201(18) 0.0511(3) Uani 1 1 d . . . C4 C -0.04583(19) 0.82378(7) 0.52471(18) 0.0328(3) Uani 1 1 d . . . H4 H -0.0963 0.8635 0.5485 0.080 Uiso 1 1 calc . . . C3 C -0.13793(18) 0.76750(7) 0.55999(18) 0.0315(3) Uani 1 1 d . . . C6 C 0.20358(18) 0.76138(7) 0.41447(18) 0.0312(3) Uani 1 1 d . . . H6 H 0.3166 0.7601 0.3650 0.080 Uiso 1 1 calc . . . C5 C 0.12258(19) 0.81913(6) 0.45336(18) 0.0320(3) Uani 1 1 d . . . C2 C -0.05891(18) 0.70888(7) 0.52417(18) 0.0311(3) Uani 1 1 d . . . H2 H -0.1203 0.6713 0.5490 0.080 Uiso 1 1 calc . . . O2 O 0.14507(17) 0.92962(5) 0.43714(18) 0.0543(3) Uani 1 1 d . . . O4 O -0.41259(17) 0.72264(6) 0.6543(2) 0.0606(4) Uani 1 1 d . . . O3 O -0.36809(15) 0.82753(6) 0.68594(17) 0.0516(3) Uani 1 1 d . . . H3 H -0.4681 0.8265 0.7289 0.080 Uiso 1 1 calc . . . C7 C -0.3208(2) 0.76925(7) 0.6373(2) 0.0376(3) Uani 1 1 d . . . N1 N 0.65853(16) 0.99353(6) 0.11228(18) 0.0381(3) Uani 1 1 d . . . H1 H 0.7174 1.0297 0.0801 0.080 Uiso 1 1 calc . . . O1 O 0.37788(18) 0.87411(6) 0.3780(2) 0.0680(4) Uani 1 1 d . . . C8 C 0.19500(18) 0.64135(7) 0.41100(19) 0.0321(3) Uani 1 1 d . . . C11 C 0.6318(2) 0.95337(7) -0.0496(2) 0.0401(4) Uani 1 1 d . . . H11A H 0.5748 0.9135 -0.0167 0.080 Uiso 1 1 calc . . . H11B H 0.7466 0.9433 -0.1008 0.080 Uiso 1 1 calc . . . C10 C 0.4819(2) 1.01242(7) 0.1864(2) 0.0408(4) Uani 1 1 d . . . H10A H 0.5005 1.0402 0.2885 0.080 Uiso 1 1 calc . . . H10B H 0.4198 0.9744 0.2267 0.080 Uiso 1 1 calc . . . C9 C 0.7695(2) 0.95902(9) 0.2467(3) 0.0555(5) Uani 1 1 d . . . H9A H 0.8819 0.9478 0.1953 0.080 Uiso 1 1 calc . . . H9B H 0.7089 0.9208 0.2832 0.080 Uiso 1 1 calc . . . H9C H 0.7892 0.9861 0.3483 0.080 Uiso 1 1 calc . . . 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 O6 0.0334(6) 0.0331(5) 0.0583(7) 0.0009(5) 0.0170(5) 0.0025(4) C1 0.0271(6) 0.0285(7) 0.0311(7) 0.0014(5) 0.0025(5) 0.0028(5) N2 0.0407(7) 0.0306(7) 0.0499(8) 0.0041(5) 0.0068(6) -0.0021(5) O5 0.0498(7) 0.0286(6) 0.0754(8) 0.0100(5) 0.0279(6) 0.0052(5) C4 0.0321(7) 0.0306(7) 0.0357(7) -0.0012(5) 0.0025(6) 0.0048(5) C3 0.0272(7) 0.0353(7) 0.0322(7) -0.0014(5) 0.0026(5) 0.0023(5) C6 0.0267(7) 0.0320(7) 0.0350(7) 0.0023(5) 0.0039(5) 0.0012(5) C5 0.0332(7) 0.0282(7) 0.0347(7) 0.0026(5) 0.0027(6) -0.0020(5) C2 0.0282(7) 0.0302(7) 0.0350(7) 0.0011(5) 0.0033(5) -0.0015(5) O2 0.0593(8) 0.0271(6) 0.0766(9) 0.0004(5) 0.0082(6) 0.0018(5) O4 0.0405(7) 0.0492(7) 0.0926(10) -0.0064(6) 0.0286(6) -0.0065(5) O3 0.0346(6) 0.0447(7) 0.0759(8) -0.0091(6) 0.0200(6) 0.0048(5) C7 0.0302(7) 0.0414(8) 0.0413(8) -0.0018(6) 0.0064(6) 0.0041(6) N1 0.0349(7) 0.0265(6) 0.0528(8) -0.0006(5) 0.0011(5) -0.0034(5) O1 0.0473(7) 0.0411(7) 0.1160(12) 0.0122(7) 0.0307(8) -0.0061(6) C8 0.0286(7) 0.0276(7) 0.0402(7) 0.0020(5) 0.0044(6) 0.0017(5) C11 0.0363(8) 0.0295(7) 0.0547(9) -0.0051(6) 0.0053(6) -0.0009(6) C10 0.0403(8) 0.0331(8) 0.0493(8) 0.0000(6) 0.0089(7) -0.0040(6) C9 0.0547(10) 0.0454(9) 0.0661(11) 0.0001(8) -0.0136(9) 0.0043(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 O6 C8 1.2458(17) . ? C1 C6 1.390(2) . ? C1 C2 1.3932(19) . ? C1 C8 1.5122(18) . ? N2 O1 1.2165(18) . ? N2 O2 1.2239(17) . ? N2 C5 1.4696(18) . ? O5 C8 1.2561(17) . ? C4 C5 1.381(2) . ? C4 C3 1.391(2) . ? C4 H4 0.9300 . ? C3 C2 1.388(2) . ? C3 C7 1.495(2) . ? C6 C5 1.384(2) . ? C6 H6 0.9300 . ? C2 H2 0.9300 . ? O4 C7 1.200(2) . ? O3 C7 1.3210(19) . ? O3 H3 0.8200 . ? N1 C9 1.488(2) . ? N1 C11 1.489(2) . ? N1 C10 1.496(2) . ? N1 H1 0.9100 . ? C11 C10 1.508(2) 3_675 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 C11 1.508(2) 3_675 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.74(12) . . ? C6 C1 C8 119.60(12) . . ? C2 C1 C8 120.65(12) . . ? O1 N2 O2 123.25(13) . . ? O1 N2 C5 118.26(12) . . ? O2 N2 C5 118.48(13) . . ? C5 C4 C3 118.22(12) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C2 C3 C4 119.67(13) . . ? C2 C3 C7 119.48(13) . . ? C4 C3 C7 120.85(13) . . ? C5 C6 C1 118.02(13) . . ? C5 C6 H6 121.0 . . ? C1 C6 H6 121.0 . . ? C4 C5 C6 123.29(13) . . ? C4 C5 N2 118.44(12) . . ? C6 C5 N2 118.26(13) . . ? C3 C2 C1 121.06(13) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C7 O3 H3 109.5 . . ? O4 C7 O3 124.19(14) . . ? O4 C7 C3 123.46(14) . . ? O3 C7 C3 112.34(13) . . ? C9 N1 C11 110.49(12) . . ? C9 N1 C10 111.58(13) . . ? C11 N1 C10 109.85(12) . . ? C9 N1 H1 108.3 . . ? C11 N1 H1 108.3 . . ? C10 N1 H1 108.3 . . ? O6 C8 O5 124.04(13) . . ? O6 C8 C1 118.37(12) . . ? O5 C8 C1 117.58(12) . . ? N1 C11 C10 111.04(12) . 3_675 ? N1 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 3_675 . ? N1 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 3_675 . ? H11A C11 H11B 108.0 . . ? N1 C10 C11 111.68(13) . 3_675 ? N1 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 3_675 . ? N1 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 3_675 . ? H10A C10 H10B 107.9 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.312 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.098 data_w2 _database_code_depnum_ccdc_archive 'CCDC 818048' #TrackingRef 'w2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C12 H17 N3 O7' _chemical_formula_sum 'C12 H17 N3 O7' _chemical_formula_weight 315.29 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 6.5078(11) _cell_length_b 19.897(2) _cell_length_c 10.9177(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1413.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 7262 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.73 _reflns_number_total 2445 _reflns_number_gt 2161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(11) _refine_ls_number_reflns 2445 _refine_ls_number_parameters 207 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N3 N 0.6239(3) 0.13663(9) 0.28094(18) 0.0378(4) Uani 1 1 d . . . C1 C 0.6292(3) 0.21044(10) 0.2711(2) 0.0294(4) Uani 1 1 d . . . O4 O 0.5930(3) 0.39842(8) 0.00538(14) 0.0454(4) Uani 1 1 d . . . C8 C 0.6242(3) 0.36078(12) 0.48108(19) 0.0374(5) Uani 1 1 d . . . C5 C 0.6243(3) 0.31778(11) 0.36730(19) 0.0294(4) Uani 1 1 d . . . O6 O 0.6087(3) 0.33104(9) 0.58166(14) 0.0521(5) Uani 1 1 d . . . C6 C 0.6232(3) 0.24861(11) 0.37689(18) 0.0304(5) Uani 1 1 d . . . H6A H 0.6186 0.2280 0.4533 0.036 Uiso 1 1 calc R . . C2 C 0.6401(3) 0.23891(10) 0.15662(18) 0.0289(4) Uani 1 1 d . . . H2A H 0.6476 0.2119 0.0872 0.035 Uiso 1 1 calc R . . O5 O 0.6421(3) 0.42278(8) 0.46859(17) 0.0601(5) Uani 1 1 d . . . C4 C 0.6286(3) 0.34741(10) 0.25120(18) 0.0277(4) Uani 1 1 d . . . H4A H 0.6237 0.3940 0.2445 0.033 Uiso 1 1 calc R . . O1 O 0.6117(3) 0.10379(8) 0.18701(17) 0.0610(5) Uani 1 1 d . . . C3 C 0.6400(3) 0.30863(10) 0.14591(18) 0.0290(4) Uani 1 1 d . . . O2 O 0.6316(3) 0.11129(9) 0.38253(18) 0.0600(5) Uani 1 1 d . . . C7 C 0.6556(3) 0.33938(11) 0.01960(18) 0.0326(5) Uani 1 1 d . . . O3 O 0.7339(3) 0.30378(8) -0.06227(15) 0.0489(4) Uani 1 1 d . . . N1 N 0.3851(3) 0.12513(9) 0.74827(17) 0.0384(4) Uani 1 1 d . . . H1A H 0.3390 0.1475 0.8144 0.080 Uiso 1 1 calc . . . H1B H 0.2890 0.1282 0.6892 0.080 Uiso 1 1 calc . . . N2 N 0.7728(3) 0.07920(9) 0.83709(18) 0.0413(5) Uani 1 1 d . . . H2B H 0.8219 0.0559 0.7727 0.080 Uiso 1 1 calc . . . H2C H 0.8663 0.0769 0.8977 0.080 Uiso 1 1 calc . . . C12 C 0.4173(3) 0.05368(11) 0.7804(2) 0.0420(5) Uani 1 1 d . . . H12A H 0.4612 0.0289 0.7085 0.050 Uiso 1 1 calc R . . H12B H 0.2892 0.0343 0.8091 0.050 Uiso 1 1 calc R . . C10 C 0.7432(3) 0.15092(12) 0.8008(2) 0.0474(6) Uani 1 1 d . . . H10A H 0.8712 0.1689 0.7692 0.057 Uiso 1 1 calc R . . H10B H 0.7042 0.1772 0.8720 0.057 Uiso 1 1 calc R . . C11 C 0.5778(4) 0.04818(11) 0.8790(2) 0.0416(5) Uani 1 1 d . . . H11A H 0.5301 0.0707 0.9525 0.050 Uiso 1 1 calc R . . H11B H 0.6009 0.0012 0.8986 0.050 Uiso 1 1 calc R . . C9 C 0.5791(4) 0.15632(12) 0.7047(2) 0.0455(6) Uani 1 1 d . . . H9A H 0.5551 0.2033 0.6855 0.055 Uiso 1 1 calc R . . H9B H 0.6245 0.1340 0.6305 0.055 Uiso 1 1 calc R . . O1W O 0.9143(4) 0.01566(10) 0.63812(18) 0.0816(8) Uani 1 1 d D . . H1WA H 0.904(6) -0.0250(10) 0.615(3) 0.104(14) Uiso 1 1 d D . . H1WB H 0.979(5) 0.0399(12) 0.588(2) 0.074(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N3 0.0383(10) 0.0295(10) 0.0456(12) 0.0042(9) 0.0003(8) -0.0001(7) C1 0.0233(9) 0.0281(10) 0.0369(12) 0.0004(9) -0.0016(9) 0.0004(7) O4 0.0649(10) 0.0345(9) 0.0368(9) 0.0035(7) -0.0078(8) 0.0079(8) C8 0.0320(11) 0.0474(14) 0.0329(12) -0.0071(10) 0.0051(9) -0.0047(9) C5 0.0232(10) 0.0323(11) 0.0325(11) -0.0023(9) 0.0021(8) -0.0018(8) O6 0.0651(12) 0.0625(12) 0.0286(9) -0.0054(8) -0.0056(8) -0.0064(8) C6 0.0264(10) 0.0381(12) 0.0267(10) 0.0046(9) 0.0004(8) -0.0026(9) C2 0.0282(11) 0.0296(11) 0.0287(10) -0.0056(9) 0.0005(8) 0.0005(8) O5 0.0863(13) 0.0408(10) 0.0531(11) -0.0170(8) 0.0235(10) -0.0171(9) C4 0.0251(9) 0.0261(10) 0.0319(11) -0.0003(8) -0.0003(8) 0.0000(7) O1 0.0968(14) 0.0292(10) 0.0569(13) -0.0086(8) -0.0016(10) -0.0004(9) C3 0.0251(10) 0.0300(10) 0.0318(11) -0.0012(10) -0.0005(9) 0.0004(8) O2 0.0841(14) 0.0390(10) 0.0568(12) 0.0167(9) -0.0034(10) -0.0051(9) C7 0.0368(12) 0.0320(12) 0.0291(11) 0.0003(9) -0.0041(9) -0.0038(9) O3 0.0766(13) 0.0387(9) 0.0312(8) -0.0001(7) 0.0144(8) 0.0024(8) N1 0.0465(10) 0.0415(11) 0.0273(9) -0.0039(8) -0.0036(8) 0.0108(8) N2 0.0418(11) 0.0451(12) 0.0369(10) -0.0091(8) -0.0053(8) 0.0077(9) C12 0.0431(12) 0.0335(12) 0.0493(14) -0.0039(10) -0.0043(11) 0.0013(9) C10 0.0499(15) 0.0414(13) 0.0510(14) -0.0080(11) 0.0060(12) -0.0052(10) C11 0.0485(14) 0.0342(13) 0.0419(13) 0.0044(9) -0.0007(11) 0.0074(10) C9 0.0624(15) 0.0373(14) 0.0366(12) 0.0049(11) 0.0126(11) 0.0064(11) O1W 0.146(2) 0.0363(11) 0.0628(13) -0.0085(10) 0.0598(14) -0.0153(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N3 O1 1.219(3) . ? N3 O2 1.219(3) . ? N3 C1 1.473(3) . ? C1 C2 1.374(3) . ? C1 C6 1.383(3) . ? O4 C7 1.253(3) . ? C8 O5 1.247(3) . ? C8 O6 1.251(3) . ? C8 C5 1.508(3) . ? C5 C6 1.380(3) . ? C5 C4 1.398(3) . ? C6 H6A 0.9300 . ? C2 C3 1.392(3) . ? C2 H2A 0.9300 . ? C4 C3 1.386(3) . ? C4 H4A 0.9300 . ? C3 C7 1.512(3) . ? C7 O3 1.249(3) . ? N1 C12 1.479(3) . ? N1 C9 1.485(3) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C11 1.484(3) . ? N2 C10 1.494(3) . ? N2 H2B 0.9000 . ? N2 H2C 0.9000 . ? C12 C11 1.503(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C10 C9 1.501(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O1W H1WA 0.852(17) . ? O1W H1WB 0.840(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 O1 N3 O2 123.13(19) . . ? O1 N3 C1 118.33(19) . . ? O2 N3 C1 118.5(2) . . ? C2 C1 C6 122.33(18) . . ? C2 C1 N3 118.61(18) . . ? C6 C1 N3 119.06(19) . . ? O5 C8 O6 124.8(2) . . ? O5 C8 C5 118.10(19) . . ? O6 C8 C5 117.0(2) . . ? C6 C5 C4 119.29(19) . . ? C6 C5 C8 120.20(18) . . ? C4 C5 C8 120.50(17) . . ? C5 C6 C1 118.95(18) . . ? C5 C6 H6A 120.5 . . ? C1 C6 H6A 120.5 . . ? C1 C2 C3 119.16(18) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C3 C4 C5 121.21(18) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C4 C3 C2 119.01(18) . . ? C4 C3 C7 122.32(18) . . ? C2 C3 C7 118.67(18) . . ? O3 C7 O4 125.1(2) . . ? O3 C7 C3 116.77(18) . . ? O4 C7 C3 118.07(18) . . ? C12 N1 C9 110.94(16) . . ? C12 N1 H1A 109.5 . . ? C9 N1 H1A 109.5 . . ? C12 N1 H1B 109.5 . . ? C9 N1 H1B 109.5 . . ? H1A N1 H1B 108.0 . . ? C11 N2 C10 111.64(17) . . ? C11 N2 H2B 109.3 . . ? C10 N2 H2B 109.3 . . ? C11 N2 H2C 109.3 . . ? C10 N2 H2C 109.3 . . ? H2B N2 H2C 108.0 . . ? N1 C12 C11 109.77(18) . . ? N1 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N1 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C10 C9 110.22(18) . . ? N2 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N2 C11 C12 110.10(18) . . ? N2 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? N2 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.2 . . ? N1 C9 C10 110.55(17) . . ? N1 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? H1WA O1W H1WB 113(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.73 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.161 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 data_w3 _database_code_depnum_ccdc_archive 'CCDC 818049' #TrackingRef 'w3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C10 H11 N O4' _chemical_formula_sum 'C10 H11 N O4' _chemical_formula_weight 209.20 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 10.3173(14) _cell_length_b 7.4516(12) _cell_length_c 26.221(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2015.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10410 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.05 _reflns_number_total 1993 _reflns_number_gt 1555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.9731P] 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 1993 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 O2 O 0.81749(14) 0.1473(2) 0.41960(5) 0.0413(4) Uani 1 1 d . . . O4 O 1.10654(15) -0.00887(19) 0.44320(6) 0.0407(4) Uani 1 1 d . . . O3 O 0.96796(15) -0.1998(2) 0.40876(6) 0.0435(4) Uani 1 1 d . . . O1 O 0.71961(15) 0.2406(2) 0.34904(6) 0.0485(5) Uani 1 1 d . . . H1 H 0.6572 0.2480 0.3683 0.080 Uiso 1 1 calc . . . C8 C 0.8197(2) 0.1811(3) 0.37417(8) 0.0301(5) Uani 1 1 d . . . C7 C 1.03719(19) -0.0584(3) 0.40773(8) 0.0300(5) Uani 1 1 d . . . C6 C 1.04019(19) 0.0491(3) 0.35879(8) 0.0298(5) Uani 1 1 d . . . C1 C 0.93890(19) 0.1597(3) 0.34262(8) 0.0304(5) Uani 1 1 d . . . C4 C 1.1612(3) 0.1321(4) 0.28377(9) 0.0514(7) Uani 1 1 d . . . H4 H 1.2352 0.1208 0.2638 0.080 Uiso 1 1 calc . . . C2 C 0.9522(2) 0.2577(3) 0.29746(8) 0.0402(5) Uani 1 1 d . . . H2 H 0.8858 0.3336 0.2870 0.080 Uiso 1 1 calc . . . C5 C 1.1512(2) 0.0369(3) 0.32894(9) 0.0423(6) Uani 1 1 d . . . H5 H 1.2194 -0.0359 0.3394 0.080 Uiso 1 1 calc . . . C3 C 1.0627(3) 0.2427(4) 0.26839(9) 0.0509(7) Uani 1 1 d . . . H3 H 1.0705 0.3077 0.2383 0.080 Uiso 1 1 calc . . . N1 N 0.48393(18) 0.1877(2) 0.50763(7) 0.0352(5) Uani 1 1 d . . . H1A H 0.5226 0.2323 0.4796 0.080 Uiso 1 1 calc . . . H1B H 0.4547 0.2806 0.5263 0.080 Uiso 1 1 calc . . . C10 C 0.3729(2) 0.0732(3) 0.49219(9) 0.0425(6) Uani 1 1 d . . . H10A H 0.3129 0.1428 0.4717 0.080 Uiso 1 1 calc . . . H10B H 0.3273 0.0315 0.5223 0.080 Uiso 1 1 calc . . . C9 C 0.5799(2) 0.0842(3) 0.53787(9) 0.0421(6) Uani 1 1 d . . . H9A H 0.5401 0.0429 0.5693 0.080 Uiso 1 1 calc . . . H9B H 0.6525 0.1609 0.5467 0.080 Uiso 1 1 calc . . . 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 O2 0.0354(9) 0.0621(10) 0.0264(8) 0.0062(7) 0.0007(7) 0.0036(8) O4 0.0425(9) 0.0393(8) 0.0403(9) 0.0012(7) -0.0138(8) -0.0062(7) O3 0.0436(9) 0.0394(9) 0.0476(10) 0.0117(7) -0.0135(8) -0.0150(7) O1 0.0367(9) 0.0761(12) 0.0328(8) 0.0073(8) 0.0014(7) 0.0204(8) C8 0.0320(11) 0.0316(10) 0.0267(11) -0.0007(9) -0.0021(9) 0.0024(9) C7 0.0234(10) 0.0288(10) 0.0379(12) 0.0001(9) -0.0012(9) 0.0027(9) C6 0.0274(11) 0.0293(10) 0.0327(11) -0.0035(9) 0.0004(9) -0.0035(8) C1 0.0312(11) 0.0319(10) 0.0280(11) 0.0001(9) 0.0000(9) -0.0015(9) C4 0.0473(15) 0.0596(16) 0.0473(15) -0.0037(13) 0.0188(12) -0.0092(13) C2 0.0452(14) 0.0434(12) 0.0320(12) 0.0061(10) 0.0001(10) -0.0003(11) C5 0.0325(12) 0.0447(13) 0.0495(15) -0.0031(11) 0.0086(11) 0.0001(10) C3 0.0603(17) 0.0575(15) 0.0348(13) 0.0083(12) 0.0087(12) -0.0104(13) N1 0.0422(11) 0.0248(8) 0.0385(10) 0.0004(8) -0.0031(8) 0.0008(8) C10 0.0282(12) 0.0396(12) 0.0596(15) 0.0063(11) -0.0035(11) 0.0009(10) C9 0.0467(14) 0.0309(11) 0.0487(14) 0.0016(10) -0.0185(11) -0.0068(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C8 1.218(2) . ? O4 C7 1.230(2) . ? O3 C7 1.273(2) . ? O1 C8 1.302(2) . ? O1 H1 0.8200 . ? C8 C1 1.491(3) . ? C7 C6 1.513(3) . ? C6 C5 1.390(3) . ? C6 C1 1.397(3) . ? C1 C2 1.398(3) . ? C4 C3 1.370(4) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C2 C3 1.376(3) . ? C2 H2 0.9300 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? N1 C9 1.484(3) . ? N1 C10 1.485(3) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? C10 C9 1.495(3) 5_656 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 C10 1.495(3) 5_656 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? 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 O1 H1 109.5 . . ? O2 C8 O1 123.42(19) . . ? O2 C8 C1 122.39(18) . . ? O1 C8 C1 114.19(17) . . ? O4 C7 O3 123.96(19) . . ? O4 C7 C6 118.05(18) . . ? O3 C7 C6 117.89(18) . . ? C5 C6 C1 118.95(19) . . ? C5 C6 C7 117.36(18) . . ? C1 C6 C7 123.68(18) . . ? C6 C1 C2 119.48(19) . . ? C6 C1 C8 120.81(18) . . ? C2 C1 C8 119.65(19) . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C9 N1 C10 111.20(16) . . ? C9 N1 H1A 109.4 . . ? C10 N1 H1A 109.4 . . ? C9 N1 H1B 109.4 . . ? C10 N1 H1B 109.4 . . ? H1A N1 H1B 108.0 . . ? N1 C10 C9 110.07(18) . 5_656 ? N1 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 5_656 . ? N1 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 5_656 . ? H10A C10 H10B 108.2 . . ? N1 C9 C10 110.08(18) . 5_656 ? N1 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 5_656 . ? N1 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 5_656 . ? H9A C9 H9B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.202 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.042 data_w4 _database_code_depnum_ccdc_archive 'CCDC 818050' #TrackingRef 'w4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C11 H15 N O6' _chemical_formula_sum 'C11 H15 N O6' _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 0.0033 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 8.4396(14) _cell_length_b 8.5941(15) _cell_length_c 8.9356(15) _cell_angle_alpha 88.535(4) _cell_angle_beta 84.804(4) _cell_angle_gamma 66.083(4) _cell_volume 589.98(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 3253 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2193 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.1993P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2193 _refine_ls_number_parameters 171 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.055 _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 O4 O 0.35244(19) 0.25542(17) 0.72405(14) 0.0395(4) Uani 1 1 d . . . O1 O 0.17154(19) -0.22739(17) 1.18369(15) 0.0426(4) Uani 1 1 d . . . O5 O 0.03577(19) 0.38303(17) 1.35769(14) 0.0402(4) Uani 1 1 d . . . H5 H 0.0071 0.3274 1.4220 0.080 Uiso 1 1 calc . . . O1W O -0.1018(2) -0.1777(2) 1.40215(15) 0.0452(4) Uani 1 1 d D . . O2 O 0.2881(2) -0.22949(18) 0.95112(16) 0.0557(5) Uani 1 1 d . . . H2 H 0.2947 -0.3273 0.9522 0.080 Uiso 1 1 calc . . . O3 O 0.3330(2) 0.47208(18) 0.86419(16) 0.0482(4) Uani 1 1 d . . . C6 C 0.1670(2) 0.3581(2) 1.10996(19) 0.0304(4) Uani 1 1 d . . . H6 H 0.1558 0.4699 1.1169 0.080 Uiso 1 1 calc . . . C8 C 0.3137(2) 0.3387(2) 0.8475(2) 0.0315(4) Uani 1 1 d . . . N1 N 0.49034(19) 0.33823(18) 0.47689(16) 0.0305(4) Uani 1 1 d . . . H1 H 0.4460 0.3256 0.5709 0.080 Uiso 1 1 calc . . . C4 C 0.1235(2) 0.1187(2) 1.22129(19) 0.0316(4) Uani 1 1 d . . . H4 H 0.0833 0.0705 1.3022 0.080 Uiso 1 1 calc . . . C1 C 0.2434(2) 0.2638(2) 0.97840(19) 0.0291(4) Uani 1 1 d . . . C2 C 0.2596(2) 0.0963(2) 0.96917(19) 0.0321(4) Uani 1 1 d . . . H3 H 0.3105 0.0328 0.8816 0.080 Uiso 1 1 calc . . . C3 C 0.2004(2) 0.0238(2) 1.08983(19) 0.0306(4) Uani 1 1 d . . . C7 C 0.2173(2) -0.1555(2) 1.0814(2) 0.0321(4) Uani 1 1 d . . . C5 C 0.1075(2) 0.2853(2) 1.23070(19) 0.0300(4) Uani 1 1 d . . . C11 C 0.6596(2) 0.3507(2) 0.4898(2) 0.0352(4) Uani 1 1 d . . . H11A H 0.7103 0.3623 0.3905 0.080 Uiso 1 1 calc . . . H11B H 0.7395 0.2473 0.5335 0.080 Uiso 1 1 calc . . . C10 C 0.3653(2) 0.4989(2) 0.4138(2) 0.0352(4) Uani 1 1 d . . . H10A H 0.2542 0.4915 0.4084 0.080 Uiso 1 1 calc . . . H10B H 0.4089 0.5139 0.3127 0.080 Uiso 1 1 calc . . . C9 C 0.5134(3) 0.1879(3) 0.3847(2) 0.0429(5) Uani 1 1 d . . . H9A H 0.4025 0.1833 0.3782 0.080 Uiso 1 1 calc . . . H9B H 0.5897 0.0860 0.4306 0.080 Uiso 1 1 calc . . . H9C H 0.5630 0.1972 0.2856 0.080 Uiso 1 1 calc . . . H1WA H -0.173(3) -0.207(3) 1.351(3) 0.063(8) Uiso 1 1 d D . . H1WB H -0.012(3) -0.191(4) 1.331(3) 0.075(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0615(9) 0.0388(7) 0.0261(7) -0.0025(6) 0.0087(6) -0.0308(7) O1 0.0604(9) 0.0344(7) 0.0356(7) 0.0051(6) 0.0078(6) -0.0246(7) O5 0.0559(9) 0.0380(7) 0.0276(7) -0.0090(6) 0.0109(6) -0.0223(7) O1W 0.0526(9) 0.0540(9) 0.0330(8) -0.0024(6) 0.0041(7) -0.0271(8) O2 0.1020(13) 0.0351(8) 0.0370(8) -0.0075(6) 0.0215(8) -0.0402(8) O3 0.0776(11) 0.0366(8) 0.0409(8) -0.0053(6) 0.0132(7) -0.0373(8) C6 0.0371(10) 0.0269(9) 0.0283(9) -0.0006(7) -0.0003(7) -0.0146(8) C8 0.0407(10) 0.0280(9) 0.0277(9) 0.0002(7) 0.0020(7) -0.0169(8) N1 0.0373(8) 0.0301(8) 0.0257(8) 0.0031(6) 0.0032(6) -0.0166(7) C4 0.0401(10) 0.0337(10) 0.0239(9) 0.0027(7) 0.0026(7) -0.0190(8) C1 0.0363(10) 0.0290(9) 0.0247(9) 0.0013(7) 0.0000(7) -0.0167(8) C2 0.0446(11) 0.0280(9) 0.0247(9) -0.0012(7) 0.0033(8) -0.0170(8) C3 0.0390(10) 0.0294(9) 0.0256(9) 0.0018(7) 0.0001(7) -0.0169(8) C7 0.0415(10) 0.0302(9) 0.0270(9) 0.0023(7) 0.0007(7) -0.0178(8) C5 0.0336(9) 0.0317(9) 0.0245(9) -0.0034(7) 0.0013(7) -0.0136(8) C11 0.0334(10) 0.0335(10) 0.0371(10) 0.0040(8) 0.0003(8) -0.0128(8) C10 0.0362(10) 0.0377(10) 0.0329(10) 0.0067(8) -0.0049(8) -0.0163(8) C9 0.0574(13) 0.0370(11) 0.0361(11) -0.0049(8) 0.0045(9) -0.0223(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C8 1.273(2) . ? O1 C7 1.211(2) . ? O5 C5 1.368(2) . ? O5 H5 0.8200 . ? O1W H1WA 0.899(16) . ? O1W H1WB 0.916(16) . ? O2 C7 1.312(2) . ? O2 H2 0.8200 . ? O3 C8 1.236(2) . ? C6 C5 1.389(2) . ? C6 C1 1.393(2) . ? C6 H6 0.9300 . ? C8 C1 1.510(2) . ? N1 C9 1.486(2) . ? N1 C11 1.490(2) . ? N1 C10 1.492(2) . ? N1 H1 0.9100 . ? C4 C5 1.386(2) . ? C4 C3 1.396(2) . ? C4 H4 0.9300 . ? C1 C2 1.394(2) . ? C2 C3 1.386(2) . ? C2 H3 0.9300 . ? C3 C7 1.492(2) . ? C11 C10 1.504(3) 2_666 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 C11 1.504(3) 2_666 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O5 H5 109.5 . . ? H1WA O1W H1WB 102.3(18) . . ? C7 O2 H2 109.5 . . ? C5 C6 C1 120.13(16) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O3 C8 O4 123.72(16) . . ? O3 C8 C1 120.16(16) . . ? O4 C8 C1 116.11(15) . . ? C9 N1 C11 111.35(15) . . ? C9 N1 C10 111.29(15) . . ? C11 N1 C10 109.79(14) . . ? C9 N1 H1 108.1 . . ? C11 N1 H1 108.1 . . ? C10 N1 H1 108.1 . . ? C5 C4 C3 119.70(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C1 C2 119.47(16) . . ? C6 C1 C8 121.00(15) . . ? C2 C1 C8 119.51(15) . . ? C3 C2 C1 120.32(16) . . ? C3 C2 H3 119.8 . . ? C1 C2 H3 119.8 . . ? C2 C3 C4 120.05(16) . . ? C2 C3 C7 120.83(16) . . ? C4 C3 C7 119.13(15) . . ? O1 C7 O2 122.71(16) . . ? O1 C7 C3 124.12(16) . . ? O2 C7 C3 113.18(15) . . ? O5 C5 C4 122.08(15) . . ? O5 C5 C6 117.58(15) . . ? C4 C5 C6 120.33(16) . . ? N1 C11 C10 110.72(15) . 2_666 ? N1 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 2_666 . ? N1 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 2_666 . ? H11A C11 H11B 108.1 . . ? N1 C10 C11 110.64(15) . 2_666 ? N1 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 2_666 . ? N1 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 2_666 . ? H10A C10 H10B 108.1 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.289 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.079 data_w5 _database_code_depnum_ccdc_archive 'CCDC 818051' #TrackingRef 'w5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C12 H4 N2 O5' _chemical_formula_sum 'C12 H4 N2 O5' _chemical_formula_weight 256.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0146(9) _cell_length_b 9.6205(7) _cell_length_c 11.9970(9) _cell_angle_alpha 90.00 _cell_angle_beta 114.8030(10) _cell_angle_gamma 90.00 _cell_volume 1258.78(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6817 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2456 _reflns_number_gt 2178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1807P)^2^+1.2848P] 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 2456 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.2579 _refine_ls_wR_factor_gt 0.2502 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 O2 O 0.61688(17) 0.2217(2) 0.09929(18) 0.0366(6) Uani 1 1 d . . . O4 O 0.08280(18) 0.0370(3) -0.28831(18) 0.0393(6) Uani 1 1 d . . . O5 O 0.2983(2) 0.0739(3) 0.25502(18) 0.0409(6) Uani 1 1 d . . . H5A H 0.3579 0.1116 0.3088 0.061 Uiso 1 1 calc R . . O3 O -0.02416(18) 0.0971(3) -0.18444(19) 0.0438(7) Uani 1 1 d . . . C2 C 0.7410(2) 0.1013(3) 0.3219(2) 0.0204(6) Uani 1 1 d . . . H2A H 0.6794 0.1175 0.2392 0.024 Uiso 1 1 calc R . . H2B H 0.8134 0.0642 0.3161 0.024 Uiso 1 1 calc R . . C7 C 0.2978(2) 0.1403(3) -0.0861(2) 0.0258(6) Uani 1 1 d . . . H7A H 0.2977 0.1515 -0.1632 0.031 Uiso 1 1 calc R . . O1 O 0.4975(2) 0.2975(3) -0.0854(2) 0.0553(8) Uani 1 1 d . . . C9 C 0.1919(2) 0.0774(3) 0.0386(2) 0.0267(6) Uani 1 1 d . . . H9A H 0.1202 0.0517 0.0451 0.032 Uiso 1 1 calc R . . C4 C 0.8073(2) 0.1141(3) 0.5819(2) 0.0211(6) Uani 1 1 d . . . H4A H 0.8645 0.1006 0.6669 0.025 Uiso 1 1 calc R . . H4B H 0.7316 0.1510 0.5806 0.025 Uiso 1 1 calc R . . C11 C 0.4046(2) 0.1441(3) 0.1334(2) 0.0260(6) Uani 1 1 d . . . H11A H 0.4762 0.1593 0.2039 0.031 Uiso 1 1 calc R . . C12 C 0.0747(2) 0.0744(3) -0.1916(2) 0.0271(6) Uani 1 1 d . . . C8 C 0.1917(2) 0.0957(3) -0.0762(2) 0.0238(6) Uani 1 1 d . . . C10 C 0.2993(2) 0.0977(3) 0.1440(2) 0.0270(6) Uani 1 1 d . . . C6 C 0.4037(2) 0.1679(3) 0.0190(2) 0.0248(6) Uani 1 1 d . . . C5 C 0.5144(2) 0.2333(3) 0.0105(2) 0.0296(6) Uani 1 1 d . . . N1 N 0.8595(3) 0.2147(3) 0.5223(3) 0.0453(7) Uani 1 1 d . . . H1A H 0.9315 0.1822 0.5267 0.080 Uiso 1 1 calc . . . H1B H 0.8736 0.2964 0.5623 0.080 Uiso 1 1 calc . . . C3 C 0.7828(3) -0.0211(3) 0.5160(3) 0.0322(7) Uani 1 1 d . . . H3A H 0.7492 -0.0862 0.5555 0.039 Uiso 1 1 calc R . . H3B H 0.8590 -0.0594 0.5198 0.039 Uiso 1 1 calc R . . N2 N 0.6937(3) -0.0024(3) 0.3838(3) 0.0427(7) Uani 1 1 d . . . H2C H 0.6819 -0.0844 0.3443 0.080 Uiso 1 1 calc . . . H2D H 0.6210 0.0265 0.3801 0.080 Uiso 1 1 calc . . . C1 C 0.7726(3) 0.2362(3) 0.3901(3) 0.0328(7) Uani 1 1 d . . . H5 H 0.6982 0.2800 0.3858 0.039 Uiso 1 1 calc R . . H6 H 0.8099 0.2978 0.3515 0.039 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 O2 0.0217(10) 0.0539(14) 0.0280(11) 0.0091(9) 0.0044(8) -0.0067(9) O4 0.0256(11) 0.0630(15) 0.0240(11) -0.0088(9) 0.0051(8) 0.0086(10) O5 0.0356(12) 0.0656(16) 0.0237(11) -0.0027(9) 0.0144(9) -0.0137(10) O3 0.0207(10) 0.0789(18) 0.0292(11) -0.0047(10) 0.0079(9) 0.0029(10) C2 0.0173(11) 0.0288(13) 0.0150(11) 0.0036(9) 0.0068(9) 0.0050(9) C7 0.0244(13) 0.0320(14) 0.0211(12) -0.0010(10) 0.0095(10) 0.0009(10) O1 0.0269(11) 0.098(2) 0.0365(13) 0.0314(13) 0.0087(9) -0.0065(12) C9 0.0226(13) 0.0308(14) 0.0273(14) -0.0023(10) 0.0111(11) -0.0034(10) C4 0.0174(11) 0.0299(13) 0.0151(11) -0.0009(9) 0.0060(9) 0.0040(9) C11 0.0202(12) 0.0339(14) 0.0198(12) -0.0003(10) 0.0044(10) 0.0001(10) C12 0.0211(13) 0.0319(14) 0.0243(13) -0.0008(10) 0.0056(10) 0.0002(10) C8 0.0208(13) 0.0248(12) 0.0229(13) -0.0023(9) 0.0065(10) 0.0011(9) C10 0.0276(14) 0.0309(14) 0.0223(13) -0.0025(10) 0.0103(11) -0.0020(10) C6 0.0211(12) 0.0285(13) 0.0236(13) 0.0011(10) 0.0082(10) 0.0008(10) C5 0.0214(13) 0.0407(15) 0.0242(13) 0.0029(11) 0.0071(10) -0.0014(11) N1 0.0423(15) 0.0425(16) 0.0474(17) -0.0008(12) 0.0154(13) -0.0047(12) C3 0.0387(16) 0.0304(14) 0.0302(15) 0.0036(11) 0.0173(12) 0.0010(12) N2 0.0464(16) 0.0407(15) 0.0426(16) -0.0028(12) 0.0202(13) -0.0045(12) C1 0.0320(14) 0.0310(14) 0.0338(15) 0.0061(11) 0.0123(12) 0.0010(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C5 1.250(3) . ? O4 C12 1.256(3) . ? O5 C10 1.357(3) . ? O5 H5A 0.8200 . ? O3 C12 1.246(4) . ? C2 N2 1.491(4) . ? C2 C1 1.495(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C7 C6 1.391(4) . ? C7 C8 1.397(4) . ? C7 H7A 0.9300 . ? O1 C5 1.246(4) . ? C9 C8 1.387(4) . ? C9 C10 1.390(4) . ? C9 H9A 0.9300 . ? C4 C3 1.487(4) . ? C4 N1 1.489(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C11 C6 1.387(4) . ? C11 C10 1.397(4) . ? C11 H11A 0.9300 . ? C12 C8 1.517(3) . ? C6 C5 1.513(4) . ? N1 C1 1.503(4) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? C3 N2 1.506(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? C1 H5 0.9700 . ? C1 H6 0.9700 . ? 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 O5 H5A 109.5 . . ? N2 C2 C1 111.8(2) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7A 119.9 . . ? C8 C7 H7A 119.9 . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C3 C4 N1 110.0(2) . . ? C3 C4 H4A 109.7 . . ? N1 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? N1 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 C11 C10 120.7(2) . . ? C6 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? O3 C12 O4 124.0(2) . . ? O3 C12 C8 117.3(2) . . ? O4 C12 C8 118.7(2) . . ? C9 C8 C7 120.1(2) . . ? C9 C8 C12 120.3(2) . . ? C7 C8 C12 119.5(2) . . ? O5 C10 C9 118.8(2) . . ? O5 C10 C11 121.6(2) . . ? C9 C10 C11 119.5(2) . . ? C11 C6 C7 119.4(2) . . ? C11 C6 C5 119.5(2) . . ? C7 C6 C5 120.9(2) . . ? O1 C5 O2 123.5(3) . . ? O1 C5 C6 117.5(2) . . ? O2 C5 C6 119.0(2) . . ? C4 N1 C1 110.5(2) . . ? C4 N1 H1A 109.6 . . ? C1 N1 H1A 109.6 . . ? C4 N1 H1B 109.6 . . ? C1 N1 H1B 109.6 . . ? H1A N1 H1B 108.1 . . ? C4 C3 N2 110.5(2) . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C2 N2 C3 110.7(2) . . ? C2 N2 H2C 109.5 . . ? C3 N2 H2C 109.5 . . ? C2 N2 H2D 109.5 . . ? C3 N2 H2D 109.5 . . ? H2C N2 H2D 108.1 . . ? C2 C1 N1 111.2(2) . . ? C2 C1 H5 109.4 . . ? N1 C1 H5 109.4 . . ? C2 C1 H6 109.4 . . ? N1 C1 H6 109.4 . . ? H5 C1 H6 108.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.840 _refine_diff_density_min -0.805 _refine_diff_density_rms 0.122 data_w61 _database_code_depnum_ccdc_archive 'CCDC 818052' #TrackingRef 'w61.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C22 H26 N2 O8' _chemical_formula_sum 'C22 H26 N2 O8' _chemical_formula_weight 446.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.941(3) _cell_length_b 11.979(2) _cell_length_c 7.0729(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.278(4) _cell_angle_gamma 90.00 _cell_volume 1071.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0001 _exptl_absorpt_correction_T_max 0.0001 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 12.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5718 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.65 _reflns_number_total 2035 _reflns_number_gt 1379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2035 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1678 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O2 O 0.64663(11) 0.42358(12) 0.0566(2) 0.0665(5) Uani 1 1 d . . . H2 H 0.6484 0.3552 0.0554 0.080 Uiso 1 1 calc . . . O4 O 0.75588(12) 0.08533(13) 0.1100(2) 0.0720(5) Uani 1 1 d . . . C5 C 0.83458(14) 0.26476(15) 0.1404(2) 0.0428(5) Uani 1 1 d . . . O1 O 0.75444(13) 0.56236(13) 0.1120(3) 0.0955(7) Uani 1 1 d . . . C4 C 0.83490(14) 0.38235(16) 0.1427(3) 0.0461(5) Uani 1 1 d . . . C11 C 0.74019(16) 0.18671(16) 0.0963(3) 0.0485(5) Uani 1 1 d . . . O3 O 0.64803(11) 0.22567(14) 0.0452(3) 0.0845(6) Uani 1 1 d . . . C6 C 0.93158(16) 0.20997(16) 0.1831(3) 0.0573(6) Uani 1 1 d . . . H6 H 0.9324 0.1323 0.1829 0.080 Uiso 1 1 calc . . . C9 C 0.93188(17) 0.43650(17) 0.1877(4) 0.0666(7) Uani 1 1 d . . . H9 H 0.9328 0.5141 0.1903 0.080 Uiso 1 1 calc . . . C10 C 0.74131(16) 0.46199(17) 0.1026(3) 0.0563(6) Uani 1 1 d . . . N1 N 0.40185(13) 0.06152(13) -0.0398(3) 0.0574(5) Uani 1 1 d . . . H1 H 0.3569 0.0022 -0.0565 0.080 Uiso 1 1 calc . . . C7 C 1.02624(16) 0.26646(19) 0.2256(4) 0.0725(7) Uani 1 1 d . . . H7 H 1.0897 0.2273 0.2522 0.080 Uiso 1 1 calc . . . C8 C 1.02639(18) 0.3802(2) 0.2286(4) 0.0785(8) Uani 1 1 d . . . H8 H 1.0899 0.4193 0.2580 0.080 Uiso 1 1 calc . . . C3 C 0.46926(17) 0.05432(17) 0.1592(3) 0.0594(6) Uani 1 1 d . . . H3A H 0.4249 0.0583 0.2536 0.080 Uiso 1 1 calc . . . H3B H 0.5177 0.1170 0.1810 0.080 Uiso 1 1 calc . . . C2 C 0.46934(17) 0.05242(17) -0.1851(3) 0.0597(6) Uani 1 1 d . . . H2A H 0.5178 0.1151 -0.1709 0.080 Uiso 1 1 calc . . . H2B H 0.4252 0.0550 -0.3143 0.080 Uiso 1 1 calc . . . C1 C 0.3369(2) 0.16500(19) -0.0661(4) 0.0829(8) Uani 1 1 d . . . H1A H 0.2933 0.1669 0.0280 0.080 Uiso 1 1 calc . . . H1B H 0.2929 0.1659 -0.1938 0.080 Uiso 1 1 calc . . . H1C H 0.3826 0.2290 -0.0494 0.080 Uiso 1 1 calc . . . 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 O2 0.0433(10) 0.0557(10) 0.0959(11) 0.0034(7) 0.0043(8) 0.0082(6) O4 0.0523(10) 0.0413(9) 0.1175(13) -0.0014(8) 0.0072(9) -0.0151(7) C5 0.0388(11) 0.0371(11) 0.0509(10) 0.0005(8) 0.0060(8) -0.0052(8) O1 0.0659(12) 0.0388(10) 0.176(2) 0.0007(10) 0.0125(12) 0.0070(8) C4 0.0372(11) 0.0385(11) 0.0609(12) 0.0007(8) 0.0066(9) -0.0013(8) C11 0.0427(12) 0.0421(12) 0.0591(11) 0.0000(9) 0.0072(9) -0.0088(9) O3 0.0405(10) 0.0592(11) 0.1435(15) 0.0010(10) -0.0034(9) -0.0111(7) C6 0.0458(12) 0.0345(11) 0.0876(15) 0.0040(10) 0.0055(10) 0.0003(8) C9 0.0450(13) 0.0347(12) 0.1154(19) 0.0003(11) 0.0065(12) -0.0058(9) C10 0.0469(13) 0.0448(13) 0.0757(14) 0.0014(10) 0.0097(11) 0.0034(9) N1 0.0461(11) 0.0431(10) 0.0802(12) -0.0025(8) 0.0070(9) -0.0157(7) C7 0.0369(12) 0.0513(14) 0.123(2) 0.0047(13) 0.0031(12) 0.0022(9) C8 0.0383(13) 0.0499(14) 0.140(2) 0.0038(13) 0.0026(13) -0.0108(10) C3 0.0593(14) 0.0536(13) 0.0659(13) -0.0070(10) 0.0145(11) -0.0186(10) C2 0.0596(14) 0.0555(13) 0.0611(12) -0.0010(10) 0.0059(10) -0.0197(10) C1 0.0683(18) 0.0489(15) 0.128(2) -0.0013(13) 0.0136(16) -0.0043(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C10 1.284(2) . ? O2 H2 0.8200 . ? O4 C11 1.232(2) . ? C5 C6 1.392(3) . ? C5 C4 1.409(3) . ? C5 C11 1.517(2) . ? O1 C10 1.214(2) . ? C4 C9 1.388(3) . ? C4 C10 1.520(3) . ? C11 O3 1.260(2) . ? C6 C7 1.376(3) . ? C6 H6 0.9300 . ? C9 C8 1.372(3) . ? C9 H9 0.9300 . ? N1 C1 1.487(3) . ? N1 C2 1.487(3) . ? N1 C3 1.492(3) . ? N1 H1 0.9100 . ? C7 C8 1.363(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C3 C2 1.496(3) 3_655 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 C3 1.496(3) 3_655 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O2 H2 109.5 . . ? C6 C5 C4 117.96(16) . . ? C6 C5 C11 113.81(17) . . ? C4 C5 C11 128.23(16) . . ? C9 C4 C5 118.04(17) . . ? C9 C4 C10 113.27(17) . . ? C5 C4 C10 128.69(16) . . ? O4 C11 O3 121.20(18) . . ? O4 C11 C5 118.65(17) . . ? O3 C11 C5 120.15(17) . . ? C7 C6 C5 122.38(19) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C8 C9 C4 122.71(19) . . ? C8 C9 H9 118.6 . . ? C4 C9 H9 118.6 . . ? O1 C10 O2 118.92(19) . . ? O1 C10 C4 120.97(19) . . ? O2 C10 C4 120.11(18) . . ? C1 N1 C2 111.96(18) . . ? C1 N1 C3 111.56(18) . . ? C2 N1 C3 109.63(16) . . ? C1 N1 H1 107.8 . . ? C2 N1 H1 107.8 . . ? C3 N1 H1 107.8 . . ? C8 C7 C6 119.58(18) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.32(18) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? N1 C3 C2 110.70(16) . 3_655 ? N1 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 3_655 . ? N1 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 3_655 . ? H3A C3 H3B 108.1 . . ? N1 C2 C3 110.65(16) . 3_655 ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 3_655 . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 3_655 . ? H2A C2 H2B 108.1 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.197 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.069 data_compound7 _database_code_depnum_ccdc_archive 'CCDC 876826' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C19 H23 N O6' _chemical_formula_sum 'C19 H23 N O6' _chemical_formula_weight 361.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.950(2) _cell_length_b 7.5242(15) _cell_length_c 16.563(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.834(2) _cell_angle_gamma 90.00 _cell_volume 1860.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type ? _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9808 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3499 _reflns_number_gt 2551 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1140P)^2^+0.6161P] 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 3499 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.2038 _refine_ls_wR_factor_gt 0.1836 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O8 O 0.16639(13) 0.1705(2) 0.61720(11) 0.0607(5) Uani 1 1 d . . . O4 O 0.29855(13) -0.0546(3) 0.64534(12) 0.0666(6) Uani 1 1 d . . . C17 C 0.14115(18) 0.3204(3) 0.64129(16) 0.0509(6) Uani 1 1 d . . . O7 O 0.07383(15) 0.3942(3) 0.60777(13) 0.0775(7) Uani 1 1 d . . . H7 H 0.0654 0.4904 0.6295 0.080 Uiso 1 1 calc . . . O6 O 0.08575(15) 0.6570(3) 0.70080(12) 0.0743(6) Uani 1 1 d . . . H6 H 0.0627 0.5894 0.6670 0.080 Uiso 1 1 calc . . . C12 C 0.16020(17) 0.5818(3) 0.73441(15) 0.0497(6) Uani 1 1 d . . . O3 O 0.23368(14) -0.2165(3) 0.54695(14) 0.0808(7) Uani 1 1 d . . . C11 C 0.19021(16) 0.4143(3) 0.70938(14) 0.0455(6) Uani 1 1 d . . . C16 C 0.26697(17) 0.3430(4) 0.74786(17) 0.0561(7) Uani 1 1 d . . . H16 H 0.2881 0.2330 0.7317 0.080 Uiso 1 1 calc . . . C4 C 0.36729(16) -0.3259(3) 0.61163(15) 0.0486(6) Uani 1 1 d . . . O2 O 0.30097(15) -0.5205(3) 0.51023(13) 0.0817(7) Uani 1 1 d . . . H2 H 0.2641 -0.4398 0.5088 0.080 Uiso 1 1 calc . . . C10 C 0.29443(18) -0.1953(4) 0.59830(16) 0.0551(7) Uani 1 1 d . . . C13 C 0.20704(19) 0.6769(3) 0.79563(16) 0.0556(7) Uani 1 1 d . . . C5 C 0.36668(17) -0.4838(4) 0.56672(15) 0.0549(7) Uani 1 1 d . . . C14 C 0.2819(2) 0.5984(4) 0.83220(18) 0.0671(8) Uani 1 1 d . . . H14 H 0.3132 0.6588 0.8736 0.080 Uiso 1 1 calc . . . C9 C 0.43635(19) -0.2962(4) 0.66940(17) 0.0610(7) Uani 1 1 d . . . H9 H 0.4370 -0.1925 0.7000 0.080 Uiso 1 1 calc . . . C7 C 0.5010(2) -0.5721(5) 0.6357(2) 0.0745(9) Uani 1 1 d . . . H7A H 0.5471 -0.6541 0.6443 0.080 Uiso 1 1 calc . . . C18 C 0.1753(3) 0.8582(4) 0.8188(2) 0.0791(10) Uani 1 1 d . . . H18A H 0.1227 0.8885 0.7862 0.080 Uiso 1 1 calc . . . H18B H 0.2215 0.9437 0.8102 0.080 Uiso 1 1 calc . . . H18C H 0.1616 0.8583 0.8748 0.080 Uiso 1 1 calc . . . C6 C 0.4343(2) -0.6092(4) 0.57850(18) 0.0636(8) Uani 1 1 d . . . C15 C 0.31177(19) 0.4332(5) 0.80930(18) 0.0684(8) Uani 1 1 d . . . H15 H 0.3622 0.3832 0.8355 0.080 Uiso 1 1 calc . . . C8 C 0.5029(2) -0.4176(5) 0.6815(2) 0.0752(9) Uani 1 1 d . . . H8 H 0.5492 -0.3974 0.7200 0.080 Uiso 1 1 calc . . . C19 C 0.4350(3) -0.7760(5) 0.5301(2) 0.0927(11) Uani 1 1 d . . . H19A H 0.3833 -0.7789 0.4934 0.080 Uiso 1 1 calc . . . H19B H 0.4338 -0.8766 0.5657 0.080 Uiso 1 1 calc . . . H19C H 0.4883 -0.7801 0.5001 0.080 Uiso 1 1 calc . . . N1 N 0.06310(13) 0.1302(2) 0.47461(11) 0.0453(5) Uani 1 1 d . . . H1N H 0.0924 0.1467 0.5235 0.080 Uiso 1 1 calc . . . C3 C -0.03207(16) 0.1747(3) 0.48309(15) 0.0492(6) Uani 1 1 d . . . H3A H -0.0651 0.1559 0.4319 0.080 Uiso 1 1 calc . . . H3B H -0.0375 0.2990 0.4975 0.080 Uiso 1 1 calc . . . C2 C 0.07115(16) -0.0605(3) 0.45266(15) 0.0478(6) Uani 1 1 d . . . H2A H 0.1337 -0.0906 0.4475 0.080 Uiso 1 1 calc . . . H2B H 0.0396 -0.0823 0.4010 0.080 Uiso 1 1 calc . . . C1 C 0.1055(2) 0.2478(4) 0.41484(19) 0.0678(8) Uani 1 1 d . . . H1A H 0.0988 0.3697 0.4305 0.080 Uiso 1 1 calc . . . H1B H 0.0770 0.2297 0.3623 0.080 Uiso 1 1 calc . . . H1C H 0.1680 0.2196 0.4133 0.080 Uiso 1 1 calc . . . 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 O8 0.0705(12) 0.0460(10) 0.0650(12) -0.0098(8) -0.0020(9) 0.0081(8) O4 0.0699(13) 0.0585(11) 0.0711(13) -0.0042(10) 0.0022(10) 0.0088(9) C17 0.0590(15) 0.0408(13) 0.0530(14) -0.0003(11) 0.0029(12) 0.0040(11) O7 0.0852(14) 0.0640(12) 0.0805(14) -0.0215(11) -0.0254(12) 0.0232(11) O6 0.0923(15) 0.0556(11) 0.0734(13) -0.0078(10) -0.0125(11) 0.0247(11) C12 0.0581(15) 0.0438(13) 0.0478(13) 0.0059(11) 0.0088(11) 0.0007(11) O3 0.0649(13) 0.0910(16) 0.0844(15) -0.0082(12) -0.0185(12) 0.0206(11) C11 0.0511(14) 0.0401(12) 0.0458(13) 0.0012(10) 0.0058(11) -0.0010(10) C16 0.0502(14) 0.0578(15) 0.0602(16) -0.0039(12) 0.0028(12) 0.0037(12) C4 0.0447(13) 0.0550(14) 0.0464(13) 0.0041(11) 0.0062(10) -0.0011(11) O2 0.0853(15) 0.0797(15) 0.0783(15) -0.0170(12) -0.0152(12) 0.0001(12) C10 0.0515(15) 0.0603(16) 0.0538(15) 0.0078(13) 0.0068(12) 0.0028(12) C13 0.0708(18) 0.0474(14) 0.0501(15) -0.0045(11) 0.0196(13) -0.0126(13) C5 0.0557(15) 0.0583(16) 0.0514(15) 0.0046(12) 0.0093(12) -0.0033(12) C14 0.0633(18) 0.081(2) 0.0579(17) -0.0176(15) 0.0076(14) -0.0213(16) C9 0.0598(16) 0.0633(17) 0.0592(16) 0.0018(13) -0.0023(13) 0.0004(13) C7 0.0629(18) 0.079(2) 0.082(2) 0.0208(18) 0.0138(17) 0.0228(16) C18 0.119(3) 0.0515(17) 0.0692(19) -0.0115(14) 0.0253(19) -0.0105(17) C6 0.0746(19) 0.0548(16) 0.0634(18) 0.0090(13) 0.0243(15) 0.0084(14) C15 0.0525(16) 0.087(2) 0.0656(18) -0.0067(16) -0.0022(13) 0.0018(15) C8 0.0598(18) 0.084(2) 0.080(2) 0.0120(17) -0.0118(15) 0.0047(16) C19 0.125(3) 0.066(2) 0.090(2) -0.0024(18) 0.032(2) 0.013(2) N1 0.0501(11) 0.0416(11) 0.0444(11) 0.0012(8) 0.0037(8) -0.0004(9) C3 0.0509(14) 0.0403(12) 0.0565(15) 0.0033(10) 0.0052(11) 0.0117(10) C2 0.0473(13) 0.0449(13) 0.0516(14) -0.0017(10) 0.0064(10) 0.0105(10) C1 0.0692(18) 0.0622(17) 0.0735(19) 0.0174(14) 0.0184(15) -0.0033(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C17 1.261(3) . ? O4 C10 1.314(3) . ? C17 O7 1.255(3) . ? C17 C11 1.492(4) . ? O7 H7 0.8200 . ? O6 C12 1.344(3) . ? O6 H6 0.8200 . ? C12 C13 1.400(4) . ? C12 C11 1.407(3) . ? O3 C10 1.223(3) . ? C11 C16 1.392(4) . ? C16 C15 1.370(4) . ? C16 H16 0.9300 . ? C4 C9 1.391(4) . ? C4 C5 1.402(4) . ? C4 C10 1.475(4) . ? O2 C5 1.351(3) . ? O2 H2 0.8200 . ? C13 C14 1.378(4) . ? C13 C18 1.500(4) . ? C5 C6 1.389(4) . ? C14 C15 1.381(4) . ? C14 H14 0.9300 . ? C9 C8 1.358(4) . ? C9 H9 0.9300 . ? C7 C6 1.370(4) . ? C7 C8 1.387(5) . ? C7 H7A 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C6 C19 1.490(5) . ? C15 H15 0.9300 . ? C8 H8 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 C3 1.475(3) . ? N1 C2 1.487(3) . ? N1 C1 1.492(3) . ? N1 H1N 0.9100 . ? C3 C2 1.508(3) 3_556 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 C3 1.508(3) 3_556 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 C17 O8 120.1(2) . . ? O7 C17 C11 118.6(2) . . ? O8 C17 C11 121.3(2) . . ? C17 O7 H7 109.5 . . ? C12 O6 H6 109.5 . . ? O6 C12 C13 117.3(2) . . ? O6 C12 C11 121.6(2) . . ? C13 C12 C11 121.0(2) . . ? C16 C11 C12 118.5(2) . . ? C16 C11 C17 121.8(2) . . ? C12 C11 C17 119.7(2) . . ? C15 C16 C11 120.7(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C9 C4 C5 119.1(2) . . ? C9 C4 C10 120.9(2) . . ? C5 C4 C10 120.0(2) . . ? C5 O2 H2 109.5 . . ? O3 C10 O4 121.9(3) . . ? O3 C10 C4 122.3(3) . . ? O4 C10 C4 115.8(2) . . ? C14 C13 C12 117.8(2) . . ? C14 C13 C18 122.5(3) . . ? C12 C13 C18 119.8(3) . . ? O2 C5 C6 117.2(3) . . ? O2 C5 C4 121.8(2) . . ? C6 C5 C4 121.0(3) . . ? C13 C14 C15 122.1(3) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C8 C9 C4 120.4(3) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? C6 C7 C8 122.9(3) . . ? C6 C7 H7A 118.6 . . ? C8 C7 H7A 118.6 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 C6 C5 117.3(3) . . ? C7 C6 C19 121.3(3) . . ? C5 C6 C19 121.4(3) . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C3 N1 C2 109.41(18) . . ? C3 N1 C1 111.8(2) . . ? C2 N1 C1 111.6(2) . . ? C3 N1 H1N 108.0 . . ? C2 N1 H1N 108.0 . . ? C1 N1 H1N 108.0 . . ? N1 C3 C2 110.31(19) . 3_556 ? N1 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 3_556 . ? N1 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 3_556 . ? H3A C3 H3B 108.1 . . ? N1 C2 C3 109.80(19) . 3_556 ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 3_556 . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 3_556 . ? H2A C2 H2B 108.2 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.400 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.048