Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Amabilino, David' 'Minguet, Maria' 'Veciana, J.' 'Vidal-Gancedo, Jose' 'Wurst, Klaus' _publ_contact_author_name 'Dr David Amabilino' _publ_contact_author_address ; Institut de Ciencia de Materials de CSIC Campus Universitari Bellaterra 08193 SPAIN ; _publ_contact_author_email 'AMABILINO@ICMAB.ES' _publ_section_title ; Racemic and Enantiomerically Pure Phenyl Alpha-Nitronyl Nitroxide Radicals: Influence of Chirality on Solution and Solid State Properties ; data_4lnn _database_code_CSD 170508 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N2 O5' _chemical_formula_weight 321.35 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.910(2) _cell_length_b 11.910(3) _cell_length_c 19.481(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1603.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 4.0 _cell_measurement_theta_max 8.5 _exptl_crystal_description platelet _exptl_crystal_colour blue _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.045 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method ? _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Siemens P4' _diffrn_measurement_method omega-scans _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1342 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 20.47 _reflns_number_total 1207 _reflns_number_observed 1048 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 22 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2918P] 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 'riding, refined at O(3)' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0122(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3.56(203) _refine_ls_number_reflns 1185 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_obs 0.0322 _refine_ls_wR_factor_all 0.0776 _refine_ls_wR_factor_obs 0.0728 _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.061 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.3851(4) 0.7617(2) 0.28064(14) 0.0415(8) Uani 1 d . . O2 O 0.2418(4) 0.4027(2) 0.35595(12) 0.0289(7) Uani 1 d . . O3 O -0.5448(4) 0.6535(2) -0.03445(15) 0.0391(8) Uani 1 d . . H3 H -0.6068(72) 0.6145(42) -0.0764(24) 0.077(17) Uiso 1 d . . O4 O -0.4938(4) 0.4723(2) -0.01283(13) 0.0363(8) Uani 1 d . . O5 O -0.2889(4) 0.5217(2) 0.09860(13) 0.0319(7) Uani 1 d . . N1 N 0.3834(5) 0.6715(3) 0.3160(2) 0.0265(9) Uani 1 d . . N2 N 0.3217(5) 0.5010(3) 0.3497(2) 0.0255(9) Uani 1 d . . C1 C 0.2706(6) 0.5793(3) 0.3036(2) 0.0251(10) Uani 1 d . . C2 C 0.4956(6) 0.6604(3) 0.3818(2) 0.0274(10) Uani 1 d . . C3 C 0.5040(6) 0.5309(3) 0.3875(2) 0.0262(10) Uani 1 d . . C4 C 0.1252(6) 0.5677(3) 0.2503(2) 0.0229(10) Uani 1 d . . C5 C 0.0228(6) 0.6601(3) 0.2257(2) 0.0270(10) Uani 1 d . . H5 H 0.0496 0.7318 0.2435 0.032 Uiso 1 calc . . C6 C -0.1167(6) 0.6484(3) 0.1759(2) 0.0267(10) Uani 1 d . . H6 H -0.1858 0.7116 0.1606 0.032 Uiso 1 calc . . C7 C -0.1554(6) 0.5442(3) 0.1485(2) 0.0252(10) Uani 1 d . . C8 C -0.0503(6) 0.4512(3) 0.1712(2) 0.0292(11) Uani 1 d . . H8 H -0.0732 0.3802 0.1518 0.035 Uiso 1 calc . . C9 C 0.0861(6) 0.4630(3) 0.2217(2) 0.0295(11) Uani 1 d . . H9 H 0.1541 0.3996 0.2373 0.035 Uiso 1 calc . . C10 C -0.4011(6) 0.6117(3) 0.0706(2) 0.0261(10) Uani 1 d . . H10 H -0.3179 0.6780 0.0623 0.031 Uiso 1 calc . . C11 C -0.4822(6) 0.5689(4) 0.0037(2) 0.0268(10) Uani 1 d . . C12 C -0.5686(6) 0.6429(4) 0.1173(2) 0.0446(13) Uani 1 d . . H12A H -0.5185 0.6706 0.1607 0.067 Uiso 1 calc . . H12B H -0.6482 0.5772 0.1256 0.067 Uiso 1 calc . . H12C H -0.6460 0.7009 0.0957 0.067 Uiso 1 calc . . C21 C 0.6916(7) 0.7177(4) 0.3757(2) 0.0406(12) Uani 1 d . . H21A H 0.7671 0.6812 0.3402 0.061 Uiso 1 calc . . H21B H 0.7594 0.7124 0.4192 0.061 Uiso 1 calc . . H21C H 0.6731 0.7962 0.3640 0.061 Uiso 1 calc . . C22 C 0.3725(7) 0.7160(4) 0.4375(2) 0.0393(12) Uani 1 d . . H22A H 0.2484 0.6782 0.4405 0.059 Uiso 1 calc . . H22B H 0.3524 0.7944 0.4261 0.059 Uiso 1 calc . . H22C H 0.4387 0.7106 0.4813 0.059 Uiso 1 calc . . C31 C 0.6687(7) 0.4782(4) 0.3461(2) 0.0395(12) Uani 1 d . . H31A H 0.6684 0.5089 0.3000 0.059 Uiso 1 calc . . H31B H 0.6507 0.3975 0.3440 0.059 Uiso 1 calc . . H31C H 0.7913 0.4949 0.3681 0.059 Uiso 1 calc . . C32 C 0.4964(6) 0.4864(3) 0.4603(2) 0.0358(11) Uani 1 d . . H32A H 0.3903 0.5218 0.4848 0.054 Uiso 1 calc . . H32B H 0.6173 0.5031 0.4835 0.054 Uiso 1 calc . . H32C H 0.4766 0.4057 0.4594 0.054 Uiso 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 O1 0.053(2) 0.032(2) 0.040(2) 0.010(2) -0.011(2) -0.010(2) O2 0.038(2) 0.023(2) 0.0253(15) 0.0017(12) 0.0027(14) -0.002(2) O3 0.051(2) 0.030(2) 0.037(2) -0.001(2) -0.017(2) 0.001(2) O4 0.040(2) 0.029(2) 0.041(2) -0.0050(14) -0.010(2) 0.002(2) O5 0.036(2) 0.029(2) 0.030(2) 0.0003(14) -0.008(2) 0.000(2) N1 0.034(2) 0.024(2) 0.022(2) 0.003(2) -0.004(2) -0.002(2) N2 0.028(2) 0.024(2) 0.024(2) 0.001(2) 0.006(2) -0.007(2) C1 0.031(3) 0.021(2) 0.023(2) 0.001(2) 0.006(2) 0.000(2) C2 0.028(2) 0.030(2) 0.025(2) -0.001(2) 0.001(2) -0.003(2) C3 0.021(2) 0.036(2) 0.021(2) 0.001(2) -0.007(2) -0.003(2) C4 0.022(2) 0.029(3) 0.017(2) 0.000(2) -0.003(2) -0.002(2) C5 0.035(3) 0.023(2) 0.023(2) -0.005(2) 0.000(2) -0.003(3) C6 0.030(3) 0.028(3) 0.022(2) 0.000(2) 0.000(2) 0.006(2) C7 0.026(3) 0.029(3) 0.021(2) 0.002(2) -0.005(2) -0.004(2) C8 0.039(3) 0.021(2) 0.028(2) -0.004(2) -0.009(2) 0.001(2) C9 0.034(3) 0.023(3) 0.031(2) 0.005(2) -0.007(2) 0.001(2) C10 0.025(2) 0.023(2) 0.030(2) 0.000(2) -0.001(2) 0.003(2) C11 0.022(3) 0.032(3) 0.027(2) 0.002(2) 0.001(2) -0.003(2) C12 0.038(3) 0.055(3) 0.041(3) -0.012(2) 0.006(3) -0.001(3) C21 0.034(3) 0.044(3) 0.044(3) 0.001(2) -0.004(3) -0.007(3) C22 0.048(3) 0.037(3) 0.032(3) -0.006(2) -0.003(2) 0.000(3) C31 0.033(3) 0.045(3) 0.040(3) 0.001(2) 0.002(2) 0.005(3) C32 0.028(2) 0.046(3) 0.033(2) 0.002(2) -0.004(2) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.276(4) . ? O2 N2 1.301(4) . ? O3 C11 1.324(5) . ? O4 C11 1.198(5) . ? O5 C7 1.366(4) . ? O5 C10 1.431(4) . ? N1 C1 1.368(5) . ? N1 C2 1.504(5) . ? N2 C1 1.341(5) . ? N2 C3 1.502(5) . ? C1 C4 1.452(5) . ? C2 C21 1.521(6) . ? C2 C22 1.529(6) . ? C2 C3 1.548(5) . ? C3 C32 1.516(5) . ? C3 C31 1.529(6) . ? C4 C9 1.392(5) . ? C4 C5 1.394(5) . ? C5 C6 1.374(5) . ? C6 C7 1.378(5) . ? C7 C8 1.397(5) . ? C8 C9 1.369(5) . ? C10 C11 1.507(5) . ? C10 C12 1.519(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 C7 O5 C10 119.4(3) . . ? O1 N1 C1 125.9(3) . . ? O1 N1 C2 121.9(3) . . ? C1 N1 C2 111.9(3) . . ? O2 N2 C1 125.2(3) . . ? O2 N2 C3 121.5(3) . . ? C1 N2 C3 112.6(3) . . ? N2 C1 N1 106.9(3) . . ? N2 C1 C4 126.5(4) . . ? N1 C1 C4 126.6(3) . . ? N1 C2 C21 110.7(3) . . ? N1 C2 C22 106.3(3) . . ? C21 C2 C22 110.8(3) . . ? N1 C2 C3 99.7(3) . . ? C21 C2 C3 114.8(4) . . ? C22 C2 C3 113.7(3) . . ? N2 C3 C32 110.3(3) . . ? N2 C3 C31 105.6(3) . . ? C32 C3 C31 112.1(3) . . ? N2 C3 C2 99.7(3) . . ? C32 C3 C2 114.5(3) . . ? C31 C3 C2 113.5(4) . . ? C9 C4 C5 118.1(3) . . ? C9 C4 C1 120.4(3) . . ? C5 C4 C1 121.5(3) . . ? C6 C5 C4 121.2(4) . . ? C5 C6 C7 120.1(4) . . ? O5 C7 C6 125.7(3) . . ? O5 C7 C8 114.9(3) . . ? C6 C7 C8 119.4(3) . . ? C9 C8 C7 120.3(3) . . ? C8 C9 C4 120.9(4) . . ? O5 C10 C11 106.2(3) . . ? O5 C10 C12 111.6(3) . . ? C11 C10 C12 108.5(3) . . ? O4 C11 O3 123.9(4) . . ? O4 C11 C10 125.6(4) . . ? O3 C11 C10 110.5(4) . . ? _refine_diff_density_max 0.136 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.033 data_d2 _database_code_CSD 170509 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N2 O5' _chemical_formula_weight 321.35 _chemical_melting_point ? _chemical_compound_source ? 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 8.5129(5) _cell_length_b 9.4113(7) _cell_length_c 10.4820(8) _cell_angle_alpha 85.847(3) _cell_angle_beta 76.415(4) _cell_angle_gamma 79.503(4) _cell_volume 802.25(10) _cell_formula_units_Z 2 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 3357 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 24.0 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method ? _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(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 'Kappa CCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3668 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 23.50 _reflns_number_total 2354 _reflns_number_observed 1957 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 82 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.4053P] 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; refined at O3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2272 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_obs 0.0430 _refine_ls_wR_factor_all 0.1111 _refine_ls_wR_factor_obs 0.1037 _refine_ls_goodness_of_fit_all 1.041 _refine_ls_goodness_of_fit_obs 1.082 _refine_ls_restrained_S_all 1.047 _refine_ls_restrained_S_obs 1.082 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2891(2) 0.3118(2) 0.80053(15) 0.0423(4) Uani 1 d . . O2 O -0.1548(2) 0.1360(2) 1.06676(14) 0.0371(4) Uani 1 d . . O3 O 0.6896(2) 0.4166(2) 1.2825(2) 0.0574(5) Uani 1 d . . H3O H 0.6837(45) 0.5168(43) 1.2606(38) 0.118(14) Uiso 1 d . . O4 O 0.4189(2) 0.4743(2) 1.3496(2) 0.0564(5) Uani 1 d . . O5 O 0.3954(2) 0.1868(2) 1.38747(14) 0.0407(4) Uani 1 d . . N1 N 0.1456(2) 0.2755(2) 0.8437(2) 0.0307(4) Uani 1 d . . N2 N -0.0653(2) 0.1968(2) 0.9708(2) 0.0276(4) Uani 1 d . . C1 C 0.0885(2) 0.2215(2) 0.9647(2) 0.0263(5) Uani 1 d . . C2 C 0.0328(3) 0.2695(2) 0.7542(2) 0.0309(5) Uani 1 d . . C3 C -0.1304(2) 0.2698(2) 0.8569(2) 0.0315(5) Uani 1 d . . C4 C 0.1718(2) 0.2023(2) 1.0729(2) 0.0278(5) Uani 1 d . . C5 C 0.3416(3) 0.1781(3) 1.0492(2) 0.0384(5) Uani 1 d . . H5 H 0.4038 0.1654 0.9627 0.046 Uiso 1 calc . . C6 C 0.4210(3) 0.1722(3) 1.1515(2) 0.0407(6) Uani 1 d . . H6 H 0.5361 0.1560 1.1344 0.049 Uiso 1 calc . . C7 C 0.3296(3) 0.1903(2) 1.2787(2) 0.0328(5) Uani 1 d . . C8 C 0.1607(3) 0.2101(2) 1.3038(2) 0.0339(5) Uani 1 d . . H8 H 0.0991 0.2191 1.3908 0.041 Uiso 1 calc . . C9 C 0.0817(2) 0.2169(2) 1.2027(2) 0.0317(5) Uani 1 d . . H9 H -0.0335 0.2314 1.2209 0.038 Uiso 1 calc . . C10 C 0.5519(3) 0.2268(2) 1.3708(2) 0.0380(5) Uani 1 d . . H10 H 0.6312 0.1691 1.3009 0.046 Uiso 1 calc . . C11 C 0.5429(3) 0.3868(2) 1.3335(2) 0.0371(5) Uani 1 d . . C12 C 0.6049(3) 0.1943(3) 1.4991(2) 0.0463(6) Uani 1 d . . H12A H 0.7114(9) 0.2216(16) 1.4908(5) 0.069 Uiso 1 calc R . H12B H 0.6118(19) 0.0917(4) 1.5208(8) 0.069 Uiso 1 calc R . H12C H 0.5255(10) 0.2487(13) 1.5681(4) 0.069 Uiso 1 calc R . C21 C 0.0347(3) 0.3976(2) 0.6567(2) 0.0415(6) Uani 1 d . . H21A H -0.0539(12) 0.4026(10) 0.6120(11) 0.062 Uiso 1 calc R . H21B H 0.1387(8) 0.3857(8) 0.5928(9) 0.062 Uiso 1 calc R . H21C H 0.0206(18) 0.4862(3) 0.7031(3) 0.062 Uiso 1 calc R . C22 C 0.0975(3) 0.1271(2) 0.6830(2) 0.0403(6) Uani 1 d . . H22A H 0.0289(11) 0.1169(8) 0.6234(11) 0.060 Uiso 1 calc R . H22B H 0.0953(17) 0.0470(3) 0.7467(2) 0.060 Uiso 1 calc R . H22C H 0.2092(7) 0.1270(7) 0.6336(12) 0.060 Uiso 1 calc R . C31 C -0.2169(3) 0.4203(3) 0.9029(2) 0.0472(6) Uani 1 d . . H31A H -0.2623(17) 0.4731(6) 0.8331(6) 0.071 Uiso 1 calc R . H31B H -0.1387(5) 0.4719(7) 0.9252(15) 0.071 Uiso 1 calc R . H31C H -0.3045(13) 0.4115(3) 0.9796(9) 0.071 Uiso 1 calc R . C32 C -0.2487(3) 0.1871(3) 0.8194(2) 0.0439(6) Uani 1 d . . H32A H -0.2847(15) 0.2340(10) 0.7433(9) 0.066 Uiso 1 calc R . H32B H -0.3429(9) 0.1852(14) 0.8922(6) 0.066 Uiso 1 calc R . H32C H -0.1943(6) 0.0889(5) 0.7988(15) 0.066 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0379(9) 0.0505(10) 0.0408(9) 0.0124(7) -0.0068(7) -0.0221(8) O2 0.0336(8) 0.0469(9) 0.0313(8) 0.0093(7) -0.0051(7) -0.0154(7) O3 0.0467(10) 0.0423(10) 0.0799(13) 0.0012(9) -0.0029(9) -0.0155(9) O4 0.0469(10) 0.0427(10) 0.0826(14) 0.0074(9) -0.0236(9) -0.0074(9) O5 0.0474(9) 0.0470(9) 0.0361(9) 0.0071(7) -0.0192(7) -0.0203(8) N1 0.0316(10) 0.0317(9) 0.0307(10) 0.0042(8) -0.0070(8) -0.0120(8) N2 0.0276(9) 0.0305(9) 0.0245(9) 0.0036(7) -0.0053(7) -0.0071(8) C1 0.0281(11) 0.0246(10) 0.0264(11) 0.0004(8) -0.0053(9) -0.0065(9) C2 0.0380(12) 0.0305(11) 0.0273(11) 0.0046(9) -0.0116(9) -0.0102(9) C3 0.0344(11) 0.0333(11) 0.0286(12) 0.0057(9) -0.0130(9) -0.0055(9) C4 0.0325(11) 0.0243(10) 0.0284(11) 0.0025(9) -0.0092(9) -0.0076(9) C5 0.0313(12) 0.0532(14) 0.0313(12) 0.0020(10) -0.0065(10) -0.0110(11) C6 0.0289(11) 0.0555(15) 0.0407(14) 0.0053(11) -0.0118(10) -0.0126(11) C7 0.0466(13) 0.0290(11) 0.0299(12) 0.0065(9) -0.0174(10) -0.0164(10) C8 0.0399(13) 0.0352(12) 0.0272(12) -0.0011(9) -0.0075(10) -0.0082(10) C9 0.0330(11) 0.0308(11) 0.0311(12) -0.0009(9) -0.0070(9) -0.0054(9) C10 0.0393(12) 0.0368(12) 0.0443(14) 0.0047(10) -0.0197(11) -0.0119(10) C11 0.0388(13) 0.0361(12) 0.0433(14) 0.0020(10) -0.0207(11) -0.0106(12) C12 0.0542(15) 0.0448(14) 0.0480(15) 0.0053(11) -0.0289(12) -0.0098(12) C21 0.0555(15) 0.0374(13) 0.0345(13) 0.0112(10) -0.0157(11) -0.0132(11) C22 0.0527(14) 0.0374(13) 0.0295(12) -0.0013(10) -0.0054(11) -0.0093(11) C31 0.0517(14) 0.0414(13) 0.0438(14) 0.0023(11) -0.0133(12) 0.0065(11) C32 0.0416(13) 0.058(2) 0.0383(13) 0.0069(11) -0.0171(11) -0.0172(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.298(2) . ? O2 N2 1.279(2) . ? O3 H3O 0.95(4) . ? O3 C11 1.310(3) . ? O4 C11 1.200(3) . ? O5 C7 1.379(2) . ? O5 C10 1.418(2) . ? N1 C1 1.345(3) . ? N1 C2 1.502(3) . ? N2 C1 1.357(2) . ? N2 C3 1.503(3) . ? C1 C4 1.456(3) . ? C2 C21 1.523(3) . ? C2 C22 1.530(3) . ? C2 C3 1.545(3) . ? C3 C32 1.513(3) . ? C3 C31 1.528(3) . ? C4 C5 1.387(3) . ? C4 C9 1.399(3) . ? C5 C6 1.389(3) . ? C6 C7 1.382(3) . ? C7 C8 1.380(3) . ? C8 C9 1.374(3) . ? C10 C12 1.510(3) . ? C10 C11 1.521(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H3O O3 C11 110.4(22) . . ? C7 O5 C10 118.4(2) . . ? O1 N1 C1 125.8(2) . . ? O1 N1 C2 121.8(2) . . ? C1 N1 C2 111.8(2) . . ? O2 N2 C1 126.1(2) . . ? O2 N2 C3 122.30(15) . . ? C1 N2 C3 111.02(15) . . ? N1 C1 N2 107.7(2) . . ? N1 C1 C4 126.3(2) . . ? N2 C1 C4 125.9(2) . . ? N1 C2 C21 110.8(2) . . ? N1 C2 C22 105.6(2) . . ? C21 C2 C22 110.8(2) . . ? N1 C2 C3 99.87(15) . . ? C21 C2 C3 114.9(2) . . ? C22 C2 C3 113.8(2) . . ? N2 C3 C32 111.3(2) . . ? N2 C3 C31 105.5(2) . . ? C32 C3 C31 110.8(2) . . ? N2 C3 C2 99.51(15) . . ? C32 C3 C2 114.9(2) . . ? C31 C3 C2 113.8(2) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C1 120.8(2) . . ? C9 C4 C1 120.5(2) . . ? C4 C5 C6 120.9(2) . . ? C7 C6 C5 119.6(2) . . ? O5 C7 C8 115.6(2) . . ? O5 C7 C6 124.4(2) . . ? C8 C7 C6 120.0(2) . . ? C9 C8 C7 120.5(2) . . ? C8 C9 C4 120.4(2) . . ? O5 C10 C12 107.7(2) . . ? O5 C10 C11 110.2(2) . . ? C12 C10 C11 110.5(2) . . ? O4 C11 O3 124.5(2) . . ? O4 C11 C10 124.8(2) . . ? O3 C11 C10 110.7(2) . . ? _refine_diff_density_max 0.401 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041 data_pm _database_code_CSD 170510 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H23 N2 O5' _chemical_formula_weight 335.37 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.307(3) _cell_length_b 10.366(3) _cell_length_c 20.439(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.11(2) _cell_angle_gamma 90.00 _cell_volume 1746.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.4 _cell_measurement_theta_max 12.5 _exptl_crystal_description prism _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method ? _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(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 'Bruker P4' _diffrn_measurement_method omega-scans _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3050 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 23.50 _reflns_number_total 2565 _reflns_number_observed 2098 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 132 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.7463P] 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 rigid _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2433 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_obs 0.0445 _refine_ls_wR_factor_all 0.1194 _refine_ls_wR_factor_obs 0.1098 _refine_ls_goodness_of_fit_all 1.047 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 1.059 _refine_ls_restrained_S_obs 1.088 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.3477(2) 0.0065(2) 0.24587(8) 0.0616(6) Uani 1 d . . O2 O 0.1062(3) -0.3524(2) 0.32761(8) 0.0720(6) Uani 1 d . . O3 O 0.2636(2) 0.08504(13) 0.55425(6) 0.0345(4) Uani 1 d . . O4 O 0.1029(2) 0.3024(2) 0.49944(8) 0.0513(5) Uani 1 d . . O5 O 0.3406(2) 0.40440(15) 0.50632(8) 0.0483(5) Uani 1 d . . N1 N 0.2743(2) -0.1013(2) 0.25037(8) 0.0347(4) Uani 1 d . . N2 N 0.1576(2) -0.2694(2) 0.28836(8) 0.0419(5) Uani 1 d . . C1 C 0.2299(2) -0.1551(2) 0.30557(9) 0.0288(5) Uani 1 d . . C2 C 0.2430(3) -0.1867(2) 0.19112(10) 0.0359(5) Uani 1 d . . C3 C 0.1242(3) -0.2867(2) 0.21502(11) 0.0485(6) Uani 1 d . . C4 C 0.2487(2) -0.0970(2) 0.37133(9) 0.0285(5) Uani 1 d . . C5 C 0.3442(2) 0.0130(2) 0.38461(10) 0.0324(5) Uani 1 d . . H5 H 0.4035 0.0454 0.3519 0.039 Uiso 1 calc . . C6 C 0.3534(2) 0.0754(2) 0.44460(10) 0.0330(5) Uani 1 d . . H6 H 0.4188 0.1491 0.4525 0.040 Uiso 1 calc . . C7 C 0.2659(2) 0.0291(2) 0.49344(9) 0.0294(5) Uani 1 d . . C8 C 0.1733(2) -0.0818(2) 0.48161(9) 0.0318(5) Uani 1 d . . H8 H 0.1163 -0.1149 0.5149 0.038 Uiso 1 calc . . C9 C 0.1641(2) -0.1441(2) 0.42177(9) 0.0315(5) Uani 1 d . . H9 H 0.1004 -0.2189 0.4146 0.038 Uiso 1 calc . . C10 C 0.3369(2) 0.2095(2) 0.56514(10) 0.0336(5) Uani 1 d . . H10 H 0.4516 0.2061 0.5565 0.040 Uiso 1 calc . . C11 C 0.3287(3) 0.2430(2) 0.63698(10) 0.0450(6) Uani 1 d . . H11A H 0.3804(17) 0.3257(8) 0.6470(2) 0.067 Uiso 1 calc R . H11B H 0.3842(17) 0.1770(8) 0.66492(10) 0.067 Uiso 1 calc R . H11C H 0.2161(3) 0.2475(15) 0.6449(2) 0.067 Uiso 1 calc R . C12 C 0.2443(3) 0.3083(2) 0.51963(10) 0.0334(5) Uani 1 d . . C13 C 0.2653(3) 0.5059(3) 0.46371(14) 0.0614(8) Uani 1 d . . H13A H 0.2372(21) 0.4723(6) 0.4195(3) 0.092 Uiso 1 calc R . H13B H 0.3406(9) 0.5772(8) 0.4626(8) 0.092 Uiso 1 calc R . H13C H 0.1679(13) 0.5359(13) 0.4807(5) 0.092 Uiso 1 calc R . C21 C 0.4062(3) -0.2416(3) 0.17945(15) 0.0710(8) Uani 1 d . . H21A H 0.3942(6) -0.2910(17) 0.1388(6) 0.106 Uiso 1 calc R . H21B H 0.4466(12) -0.2974(16) 0.2159(5) 0.106 Uiso 1 calc R . H21C H 0.4823(8) -0.1717(3) 0.1761(10) 0.106 Uiso 1 calc R . C22 C 0.1741(4) -0.1061(3) 0.13234(12) 0.0569(7) Uani 1 d . . H22A H 0.1357(21) -0.1625(3) 0.0958(3) 0.085 Uiso 1 calc R . H22B H 0.2579(7) -0.0497(13) 0.1195(6) 0.085 Uiso 1 calc R . H22C H 0.0845(15) -0.0545(13) 0.1441(3) 0.085 Uiso 1 calc R . C31 C 0.1523(6) -0.4252(3) 0.19740(15) 0.0950(13) Uani 1 d . . H31A H 0.1387(33) -0.4346(6) 0.14982(15) 0.143 Uiso 1 calc R . H31B H 0.0748(21) -0.4799(4) 0.2160(11) 0.143 Uiso 1 calc R . H31C H 0.2616(12) -0.4504(8) 0.2150(11) 0.143 Uiso 1 calc R . C32 C -0.0556(3) -0.2511(4) 0.19674(14) 0.0771(9) Uani 1 d . . H32A H -0.0877(8) -0.2687(21) 0.1504(3) 0.116 Uiso 1 calc R . H32B H -0.0707(6) -0.1601(6) 0.2053(10) 0.116 Uiso 1 calc R . H32C H -0.1216(4) -0.3019(16) 0.2230(8) 0.116 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0961(14) 0.0547(11) 0.0355(9) -0.0013(8) 0.0135(9) -0.0365(10) O2 0.134(2) 0.0431(10) 0.0410(10) -0.0020(8) 0.0180(10) -0.0377(11) O3 0.0460(9) 0.0320(8) 0.0257(7) -0.0040(6) 0.0057(6) -0.0054(7) O4 0.0350(9) 0.0533(11) 0.0626(11) 0.0164(8) -0.0057(8) -0.0068(8) O5 0.0403(9) 0.0424(9) 0.0590(10) 0.0146(8) -0.0069(7) -0.0104(7) N1 0.0446(10) 0.0313(10) 0.0284(9) -0.0010(8) 0.0050(8) -0.0069(8) N2 0.0663(13) 0.0300(10) 0.0300(10) -0.0010(8) 0.0087(9) -0.0099(9) C1 0.0325(11) 0.0254(10) 0.0284(10) 0.0007(8) 0.0031(8) 0.0002(9) C2 0.0468(13) 0.0344(12) 0.0263(10) -0.0052(9) 0.0036(9) 0.0031(10) C3 0.079(2) 0.0370(13) 0.0299(12) -0.0084(10) 0.0081(11) -0.0156(12) C4 0.0298(10) 0.0283(11) 0.0267(10) 0.0015(8) 0.0009(8) 0.0031(9) C5 0.0340(11) 0.0346(11) 0.0294(11) 0.0013(9) 0.0065(8) -0.0046(9) C6 0.0356(11) 0.0327(11) 0.0309(11) -0.0024(9) 0.0045(9) -0.0090(9) C7 0.0311(11) 0.0309(11) 0.0253(10) 0.0003(9) -0.0001(8) 0.0026(9) C8 0.0366(11) 0.0305(11) 0.0292(11) 0.0035(9) 0.0071(8) -0.0021(9) C9 0.0360(11) 0.0277(11) 0.0303(11) 0.0014(9) 0.0025(9) -0.0061(9) C10 0.0370(11) 0.0306(11) 0.0316(11) -0.0025(9) -0.0022(9) -0.0033(9) C11 0.0614(15) 0.0411(13) 0.0300(11) -0.0062(10) -0.0045(10) 0.0011(12) C12 0.0360(12) 0.0341(12) 0.0297(11) -0.0030(9) 0.0028(9) -0.0042(10) C13 0.058(2) 0.050(2) 0.072(2) 0.0271(14) -0.0077(13) -0.0083(13) C21 0.069(2) 0.084(2) 0.063(2) -0.016(2) 0.0180(14) 0.022(2) C22 0.079(2) 0.0496(15) 0.0381(13) 0.0050(11) -0.0089(12) -0.0086(14) C31 0.198(4) 0.038(2) 0.054(2) -0.0158(14) 0.033(2) -0.019(2) C32 0.065(2) 0.108(3) 0.055(2) -0.010(2) -0.0019(14) -0.035(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.283(2) . ? O2 N2 1.285(2) . ? O3 C7 1.374(2) . ? O3 C10 1.433(2) . ? O4 C12 1.198(2) . ? O5 C12 1.327(3) . ? O5 C13 1.457(3) . ? N1 C1 1.350(3) . ? N1 C2 1.496(3) . ? N2 C1 1.356(3) . ? N2 C3 1.501(3) . ? C1 C4 1.463(3) . ? C2 C22 1.516(3) . ? C2 C21 1.517(3) . ? C2 C3 1.551(3) . ? C3 C31 1.505(4) . ? C3 C32 1.539(4) . ? C4 C5 1.396(3) . ? C4 C9 1.405(3) . ? C5 C6 1.380(3) . ? C6 C7 1.391(3) . ? C7 C8 1.388(3) . ? C8 C9 1.377(3) . ? C10 C11 1.519(3) . ? C10 C12 1.526(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O3 C10 117.9(2) . . ? C12 O5 C13 116.1(2) . . ? O1 N1 C1 127.0(2) . . ? O1 N1 C2 119.6(2) . . ? C1 N1 C2 113.2(2) . . ? O2 N2 C1 126.5(2) . . ? O2 N2 C3 120.6(2) . . ? C1 N2 C3 112.6(2) . . ? N1 C1 N2 107.6(2) . . ? N1 C1 C4 126.1(2) . . ? N2 C1 C4 126.3(2) . . ? N1 C2 C22 109.1(2) . . ? N1 C2 C21 106.3(2) . . ? C22 C2 C21 109.8(2) . . ? N1 C2 C3 101.2(2) . . ? C22 C2 C3 115.2(2) . . ? C21 C2 C3 114.5(2) . . ? N2 C3 C31 109.7(2) . . ? N2 C3 C32 105.5(2) . . ? C31 C3 C32 110.2(3) . . ? N2 C3 C2 100.9(2) . . ? C31 C3 C2 116.0(2) . . ? C32 C3 C2 113.5(2) . . ? C5 C4 C9 117.7(2) . . ? C5 C4 C1 120.6(2) . . ? C9 C4 C1 121.6(2) . . ? C6 C5 C4 121.6(2) . . ? C5 C6 C7 120.0(2) . . ? O3 C7 C8 116.0(2) . . ? O3 C7 C6 124.8(2) . . ? C8 C7 C6 119.2(2) . . ? C9 C8 C7 120.8(2) . . ? C8 C9 C4 120.7(2) . . ? O3 C10 C11 106.6(2) . . ? O3 C10 C12 109.7(2) . . ? C11 C10 C12 110.9(2) . . ? O4 C12 O5 123.9(2) . . ? O4 C12 C10 125.1(2) . . ? O5 C12 C10 111.0(2) . . ? 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 N1 C2 C3 N2 -19.6(2) . . . . ? N2 C3 C2 N1 -19.6(2) . . . . ? N1 C1 C4 C5 -12.0(3) . . . . ? C5 C4 C1 N1 -12.0(3) . . . . ? N2 C1 C4 C9 -12.6(3) . . . . ? C9 C4 C1 N2 -12.6(3) . . . . ? _refine_diff_density_max 0.351 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.049