# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_global data_1 #TrackingRef 'compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N2 O4' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.412(19) _cell_length_b 4.442(3) _cell_length_c 15.994(11) _cell_angle_alpha 90.00 _cell_angle_beta 113.034(12) _cell_angle_gamma 90.00 _cell_volume 1727(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9429 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4415 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.38 _reflns_number_total 1751 _reflns_number_gt 985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART V5.624' _computing_cell_refinement 'Siemens SAINT V6.02A' _computing_data_reduction 'Siemens SAINT and XPREP Version 6.12' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.1131P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1751 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1892 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.32253(8) 1.3261(5) 0.54616(14) 0.0417(6) Uani 1 1 d . . . O2 O 0.41737(9) 1.1729(5) 0.52919(15) 0.0430(7) Uani 1 1 d . . . H2O H 0.4439(16) 1.098(9) 0.519(2) 0.068(13) Uiso 1 1 d . . . O3 O 0.45895(8) 0.8156(6) 0.44138(15) 0.0501(7) Uani 1 1 d . . . O4 O 0.40231(8) 0.5310(5) 0.33028(15) 0.0421(6) Uani 1 1 d . . . N1 N 0.27620(9) 0.9932(5) 0.43737(16) 0.0327(6) Uani 1 1 d . . . H1A H 0.2461 1.0436 0.4425 0.039 Uiso 1 1 calc R . . N2 N 0.31612(9) 0.6876(5) 0.36332(16) 0.0322(6) Uani 1 1 d . . . C1 C 0.32311(12) 1.1340(7) 0.4918(2) 0.0329(7) Uani 1 1 d . . . C2 C 0.37086(11) 1.0350(7) 0.4779(2) 0.0315(7) Uani 1 1 d . . . C3 C 0.36520(11) 0.8185(7) 0.41542(19) 0.0301(7) Uani 1 1 d . . . C4 C 0.27344(11) 0.7790(7) 0.37548(19) 0.0300(7) Uani 1 1 d . . . C5 C 0.21802(12) 0.6607(8) 0.3207(2) 0.0409(8) Uani 1 1 d . . . H5A H 0.2213 0.4748 0.2926 0.061 Uiso 1 1 calc R . . H5B H 0.1983 0.8042 0.2745 0.061 Uiso 1 1 calc R . . H5C H 0.1984 0.6261 0.3593 0.061 Uiso 1 1 calc R . . C6 C 0.41374(12) 0.7220(7) 0.3982(2) 0.0353(8) Uani 1 1 d . . . C7 C 0.44805(12) 0.4371(8) 0.3080(2) 0.0456(9) Uani 1 1 d . . . H7A H 0.4731 0.3111 0.3560 0.055 Uiso 1 1 calc R . . H7B H 0.4682 0.6112 0.3009 0.055 Uiso 1 1 calc R . . C8 C 0.42459(13) 0.2660(9) 0.2218(2) 0.0538(10) Uani 1 1 d . . . H8A H 0.4538 0.1937 0.2058 0.081 Uiso 1 1 calc R . . H8B H 0.4009 0.3951 0.1745 0.081 Uiso 1 1 calc R . . H8C H 0.4038 0.0984 0.2293 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0351(12) 0.0468(14) 0.0459(14) -0.0122(11) 0.0188(11) -0.0016(10) O2 0.0232(11) 0.0509(15) 0.0514(15) -0.0136(11) 0.0109(10) -0.0042(10) O3 0.0196(11) 0.0613(16) 0.0662(16) -0.0164(12) 0.0132(10) -0.0030(10) O4 0.0228(11) 0.0526(15) 0.0551(14) -0.0149(11) 0.0199(10) -0.0007(10) N1 0.0213(12) 0.0403(16) 0.0374(15) -0.0016(12) 0.0125(11) 0.0035(11) N2 0.0229(12) 0.0378(15) 0.0354(15) -0.0001(11) 0.0108(11) 0.0007(11) C1 0.0304(16) 0.0331(17) 0.0350(18) 0.0025(14) 0.0126(13) 0.0001(13) C2 0.0216(14) 0.0356(18) 0.0352(17) -0.0004(14) 0.0088(12) -0.0007(12) C3 0.0208(14) 0.0351(17) 0.0340(17) 0.0026(14) 0.0103(12) 0.0011(12) C4 0.0259(15) 0.0338(18) 0.0312(17) 0.0052(13) 0.0121(12) 0.0023(13) C5 0.0244(15) 0.052(2) 0.045(2) -0.0060(15) 0.0123(14) 0.0006(14) C6 0.0246(15) 0.0381(19) 0.0447(19) 0.0007(15) 0.0151(13) 0.0006(13) C7 0.0227(15) 0.060(2) 0.061(2) -0.0089(18) 0.0239(15) 0.0033(15) C8 0.0287(18) 0.076(3) 0.059(2) -0.015(2) 0.0201(17) 0.0030(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.222(4) . ? O2 C2 1.330(3) . ? O2 H2O 0.85(4) . ? O3 C6 1.196(4) . ? O4 C6 1.317(4) . ? O4 C7 1.448(3) . ? N1 C4 1.354(4) . ? N1 C1 1.357(4) . ? N1 H1A 0.8600 . ? N2 C4 1.282(4) . ? N2 C3 1.367(4) . ? C1 C2 1.433(4) . ? C2 C3 1.352(4) . ? C3 C6 1.476(4) . ? C4 C5 1.478(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 C8 1.481(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 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 C2 O2 H2O 110(3) . . ? C6 O4 C7 116.4(2) . . ? C4 N1 C1 124.6(2) . . ? C4 N1 H1A 117.7 . . ? C1 N1 H1A 117.7 . . ? C4 N2 C3 117.0(3) . . ? O1 C1 N1 121.1(3) . . ? O1 C1 C2 125.6(3) . . ? N1 C1 C2 113.4(3) . . ? O2 C2 C3 126.3(3) . . ? O2 C2 C1 114.8(3) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 N2 123.9(3) . . ? C2 C3 C6 119.4(3) . . ? N2 C3 C6 116.6(3) . . ? N2 C4 N1 122.3(3) . . ? N2 C4 C5 121.5(3) . . ? N1 C4 C5 116.2(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 O4 123.7(3) . . ? O3 C6 C3 122.3(3) . . ? O4 C6 C3 113.9(3) . . ? O4 C7 C8 106.9(2) . . ? O4 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? O4 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C4 N1 C1 O1 179.9(3) . . . . ? C4 N1 C1 C2 0.2(4) . . . . ? O1 C1 C2 O2 -0.8(5) . . . . ? N1 C1 C2 O2 178.9(2) . . . . ? O1 C1 C2 C3 179.6(3) . . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? O2 C2 C3 N2 -178.9(3) . . . . ? C1 C2 C3 N2 0.6(5) . . . . ? O2 C2 C3 C6 -1.6(5) . . . . ? C1 C2 C3 C6 178.0(3) . . . . ? C4 N2 C3 C2 0.0(4) . . . . ? C4 N2 C3 C6 -177.4(3) . . . . ? C3 N2 C4 N1 -0.6(4) . . . . ? C3 N2 C4 C5 177.9(3) . . . . ? C1 N1 C4 N2 0.5(5) . . . . ? C1 N1 C4 C5 -178.0(3) . . . . ? C7 O4 C6 O3 -0.7(5) . . . . ? C7 O4 C6 C3 177.8(3) . . . . ? C2 C3 C6 O3 4.5(5) . . . . ? N2 C3 C6 O3 -178.0(3) . . . . ? C2 C3 C6 O4 -174.0(3) . . . . ? N2 C3 C6 O4 3.5(4) . . . . ? C6 O4 C7 C8 -170.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O3 0.85(4) 1.91(4) 2.628(3) 141(4) . N1 H1A O1 0.86 1.98 2.837(4) 178.0 7_576 O2 H2O O3 0.85(4) 2.42(4) 3.113(4) 139(3) 5_676 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.305 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 926545' ####################################################################### # # 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_global # Attachment 'compound 2.cif' data_2 #TrackingRef 'compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N2 O4' _chemical_formula_sum 'C16 H18 N2 O4' _chemical_formula_weight 302.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6417(19) _cell_length_b 8.0586(15) _cell_length_c 18.579(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.853(4) _cell_angle_gamma 90.00 _cell_volume 1581.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9554 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8387 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3005 _reflns_number_gt 1502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART V5.624' _computing_cell_refinement 'Siemens SAINT V6.02A' _computing_data_reduction 'Siemens SAINT and XPREP Version 6.12' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.1086P)^2^+0.0195P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3005 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1298 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.2078 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3626(2) 0.8384(3) -0.00376(13) 0.0880(8) Uani 1 1 d . . . N1 N 0.2441(2) 1.0724(3) 0.00567(12) 0.0579(7) Uani 1 1 d . . . C1 C 0.2803(3) 0.9108(4) 0.02495(15) 0.0598(8) Uani 1 1 d . . . O2 O 0.23670(17) 0.6811(3) 0.10297(12) 0.0700(6) Uani 1 1 d . . . N2 N 0.0881(2) 1.0876(3) 0.08497(12) 0.0596(7) Uani 1 1 d . . . C2 C 0.2137(3) 0.8411(4) 0.08102(16) 0.0575(8) Uani 1 1 d . . . O3 O -0.0535(2) 0.8388(4) 0.16438(14) 0.1250(12) Uani 1 1 d . . . C3 C 0.1239(3) 0.9332(4) 0.10862(14) 0.0553(7) Uani 1 1 d . . . O4 O 0.1315(2) 0.8621(3) 0.23027(12) 0.0863(8) Uani 1 1 d . . . C4 C 0.1491(3) 1.1536(4) 0.03541(16) 0.0580(8) Uani 1 1 d . . . C5 C 0.1147(3) 1.3251(4) 0.01070(19) 0.0810(10) Uani 1 1 d . . . H5A H 0.0475 1.3655 0.0361 0.121 Uiso 1 1 calc R . . H5B H 0.0874 1.3243 -0.0404 0.121 Uiso 1 1 calc R . . H5C H 0.1872 1.3962 0.0205 0.121 Uiso 1 1 calc R . . C6 C 0.0558(3) 0.8692(4) 0.16931(18) 0.0688(9) Uani 1 1 d . . . C7 C 0.3147(3) 1.1533(5) -0.04881(18) 0.0886(11) Uani 1 1 d . . . H7A H 0.2820 1.2630 -0.0587 0.133 Uiso 1 1 calc R . . H7B H 0.3052 1.0893 -0.0927 0.133 Uiso 1 1 calc R . . H7C H 0.4028 1.1599 -0.0303 0.133 Uiso 1 1 calc R . . C8 C 0.3622(3) 0.6535(4) 0.1413(3) 0.1028(14) Uani 1 1 d . . . H8A H 0.3751 0.7233 0.1841 0.123 Uiso 1 1 calc R . . H8B H 0.4263 0.6807 0.1102 0.123 Uiso 1 1 calc R . . C9 C 0.3718(3) 0.4750(4) 0.16246(18) 0.0629(8) Uani 1 1 d . . . C10 C 0.4496(3) 0.3687(5) 0.13081(18) 0.0791(10) Uani 1 1 d . . . H10A H 0.4957 0.4073 0.0948 0.095 Uiso 1 1 calc R . . C11 C 0.4600(3) 0.2022(6) 0.1525(2) 0.0901(12) Uani 1 1 d . . . H11A H 0.5136 0.1307 0.1314 0.108 Uiso 1 1 calc R . . C12 C 0.3915(4) 0.1463(5) 0.2043(2) 0.0841(11) Uani 1 1 d . . . H12A H 0.3988 0.0362 0.2192 0.101 Uiso 1 1 calc R . . C13 C 0.3128(4) 0.2492(6) 0.2346(2) 0.0858(11) Uani 1 1 d . . . H13A H 0.2643 0.2096 0.2693 0.103 Uiso 1 1 calc R . . C14 C 0.3046(3) 0.4116(5) 0.2139(2) 0.0772(10) Uani 1 1 d . . . H14A H 0.2511 0.4817 0.2358 0.093 Uiso 1 1 calc R . . C15 C 0.0771(4) 0.8106(6) 0.29558(19) 0.1115(15) Uani 1 1 d . . . H15A H 0.0035 0.8778 0.3017 0.134 Uiso 1 1 calc R . . H15B H 0.0508 0.6954 0.2914 0.134 Uiso 1 1 calc R . . C16 C 0.1707(4) 0.8309(7) 0.3559(2) 0.145(2) Uani 1 1 d . . . H16A H 0.1372 0.7959 0.3992 0.217 Uiso 1 1 calc R . . H16B H 0.1947 0.9456 0.3603 0.217 Uiso 1 1 calc R . . H16C H 0.2434 0.7649 0.3491 0.217 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0718(15) 0.1048(19) 0.0906(17) -0.0079(14) 0.0228(13) 0.0252(13) N1 0.0496(13) 0.0696(18) 0.0541(14) 0.0046(13) 0.0047(11) 0.0053(13) C1 0.0515(16) 0.071(2) 0.0560(17) -0.0053(16) 0.0027(15) 0.0056(16) O2 0.0565(12) 0.0525(13) 0.0965(16) 0.0049(11) -0.0101(11) 0.0010(10) N2 0.0588(14) 0.0604(17) 0.0597(15) 0.0012(13) 0.0076(12) 0.0078(13) C2 0.0504(16) 0.055(2) 0.0638(19) -0.0032(15) -0.0046(14) -0.0007(14) O3 0.0686(17) 0.216(3) 0.0900(19) 0.0215(19) 0.0086(14) -0.0429(18) C3 0.0517(16) 0.062(2) 0.0512(16) -0.0017(15) 0.0036(13) -0.0036(15) O4 0.0766(14) 0.120(2) 0.0611(13) 0.0209(13) 0.0043(12) -0.0301(13) C4 0.0560(17) 0.060(2) 0.0552(17) -0.0021(15) -0.0033(15) 0.0025(15) C5 0.092(2) 0.068(2) 0.083(2) 0.0143(18) 0.0096(19) 0.0130(19) C6 0.062(2) 0.075(2) 0.068(2) -0.0005(17) 0.0044(17) -0.0102(17) C7 0.068(2) 0.123(3) 0.077(2) 0.027(2) 0.0222(18) 0.006(2) C8 0.064(2) 0.074(3) 0.161(4) 0.033(2) -0.031(2) -0.0040(17) C9 0.0451(16) 0.057(2) 0.083(2) 0.0049(17) -0.0042(16) 0.0020(15) C10 0.061(2) 0.103(3) 0.074(2) 0.001(2) 0.0116(17) -0.002(2) C11 0.067(2) 0.087(3) 0.114(3) -0.033(3) 0.001(2) 0.023(2) C12 0.080(2) 0.062(2) 0.102(3) 0.003(2) -0.025(2) 0.004(2) C13 0.093(3) 0.080(3) 0.084(2) 0.002(2) 0.010(2) -0.015(2) C14 0.068(2) 0.069(3) 0.097(3) -0.018(2) 0.022(2) 0.0016(18) C15 0.099(3) 0.165(4) 0.072(2) 0.040(3) 0.017(2) -0.028(3) C16 0.106(3) 0.260(7) 0.067(3) 0.019(3) 0.008(2) -0.029(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.226(3) . ? N1 C4 1.374(3) . ? N1 C1 1.393(4) . ? N1 C7 1.482(4) . ? C1 C2 1.442(4) . ? O2 C2 1.366(3) . ? O2 C8 1.454(4) . ? N2 C4 1.302(3) . ? N2 C3 1.359(4) . ? C2 C3 1.357(4) . ? O3 C6 1.182(3) . ? C3 C6 1.502(4) . ? O4 C6 1.310(4) . ? O4 C15 1.465(4) . ? C4 C5 1.488(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.492(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.358(4) . ? C9 C10 1.372(4) . ? C10 C11 1.401(5) . ? C10 H10A 0.9300 . ? C11 C12 1.353(5) . ? C11 H11A 0.9300 . ? C12 C13 1.347(5) . ? C12 H12A 0.9300 . ? C13 C14 1.364(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.417(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C4 N1 C1 122.4(3) . . ? C4 N1 C7 121.5(3) . . ? C1 N1 C7 116.1(3) . . ? O1 C1 N1 121.5(3) . . ? O1 C1 C2 124.5(3) . . ? N1 C1 C2 113.9(3) . . ? C2 O2 C8 114.3(2) . . ? C4 N2 C3 117.3(2) . . ? C3 C2 O2 120.8(3) . . ? C3 C2 C1 119.3(3) . . ? O2 C2 C1 119.8(3) . . ? C2 C3 N2 124.1(3) . . ? C2 C3 C6 121.3(3) . . ? N2 C3 C6 114.6(3) . . ? C6 O4 C15 117.7(3) . . ? N2 C4 N1 122.9(3) . . ? N2 C4 C5 118.2(3) . . ? N1 C4 C5 118.9(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 O4 123.7(3) . . ? O3 C6 C3 124.8(3) . . ? O4 C6 C3 111.3(3) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C9 107.8(2) . . ? O2 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O2 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.5 . . ? C14 C9 C10 117.5(3) . . ? C14 C9 C8 121.5(3) . . ? C10 C9 C8 121.0(3) . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C13 C12 C11 120.4(4) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 119.6(4) . . ? C12 C13 H13A 120.2 . . ? C14 C13 H13A 120.2 . . ? C9 C14 C13 122.5(3) . . ? C9 C14 H14A 118.7 . . ? C13 C14 H14A 118.7 . . ? C16 C15 O4 108.2(3) . . ? C16 C15 H15A 110.1 . . ? O4 C15 H15A 110.1 . . ? C16 C15 H15B 110.1 . . ? O4 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C4 N1 C1 O1 177.7(2) . . . . ? C7 N1 C1 O1 -2.7(4) . . . . ? C4 N1 C1 C2 -2.9(4) . . . . ? C7 N1 C1 C2 176.7(2) . . . . ? C8 O2 C2 C3 -115.3(3) . . . . ? C8 O2 C2 C1 68.2(4) . . . . ? O1 C1 C2 C3 -179.8(3) . . . . ? N1 C1 C2 C3 0.9(4) . . . . ? O1 C1 C2 O2 -3.2(4) . . . . ? N1 C1 C2 O2 177.5(2) . . . . ? O2 C2 C3 N2 -174.0(2) . . . . ? C1 C2 C3 N2 2.5(4) . . . . ? O2 C2 C3 C6 6.1(4) . . . . ? C1 C2 C3 C6 -177.3(3) . . . . ? C4 N2 C3 C2 -3.8(4) . . . . ? C4 N2 C3 C6 176.0(2) . . . . ? C3 N2 C4 N1 1.6(4) . . . . ? C3 N2 C4 C5 -177.8(3) . . . . ? C1 N1 C4 N2 1.8(4) . . . . ? C7 N1 C4 N2 -177.8(3) . . . . ? C1 N1 C4 C5 -178.8(3) . . . . ? C7 N1 C4 C5 1.6(4) . . . . ? C15 O4 C6 O3 1.1(6) . . . . ? C15 O4 C6 C3 176.7(3) . . . . ? C2 C3 C6 O3 -114.5(4) . . . . ? N2 C3 C6 O3 65.6(4) . . . . ? C2 C3 C6 O4 69.9(4) . . . . ? N2 C3 C6 O4 -109.9(3) . . . . ? C2 O2 C8 C9 179.1(3) . . . . ? O2 C8 C9 C14 -69.2(4) . . . . ? O2 C8 C9 C10 111.2(3) . . . . ? C14 C9 C10 C11 -1.2(5) . . . . ? C8 C9 C10 C11 178.4(3) . . . . ? C9 C10 C11 C12 0.8(5) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C11 C12 C13 C14 -1.6(5) . . . . ? C10 C9 C14 C13 0.3(5) . . . . ? C8 C9 C14 C13 -179.4(3) . . . . ? C12 C13 C14 C9 1.1(5) . . . . ? C6 O4 C15 C16 -173.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.222 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 926546' ####################################################################### # # 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_global # Attachment 'compound 3.cif' data_3 #TrackingRef 'compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 N3 O3' _chemical_formula_sum 'C8 H11 N3 O3' _chemical_formula_weight 197.20 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.600(2) _cell_length_b 7.8212(11) _cell_length_c 14.414(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.112(2) _cell_angle_gamma 90.00 _cell_volume 1806.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5823 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.72 _reflns_number_total 2192 _reflns_number_gt 1870 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART V5.624' _computing_cell_refinement 'Siemens SAINT V6.02A' _computing_data_reduction 'Siemens SAINT and XPREP Version 6.12' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0569P)^2^+0.8675P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2192 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.20044(6) 0.99070(13) 0.10367(7) 0.0190(2) Uani 1 1 d . . . O1 O 0.26711(6) 0.85698(13) 0.24448(6) 0.0252(2) Uani 1 1 d . . . C1 C 0.26638(8) 0.89841(16) 0.16225(9) 0.0193(3) Uani 1 1 d . . . O2 O 0.39705(6) 0.76657(12) 0.16992(6) 0.0218(2) Uani 1 1 d . . . H2O H 0.4315(13) 0.754(3) 0.1309(16) 0.052(6) Uiso 1 1 d . . . C2 C 0.33254(7) 0.85742(15) 0.11667(9) 0.0180(3) Uani 1 1 d . . . N2 N 0.25920(6) 1.00295(13) -0.02782(7) 0.0184(2) Uani 1 1 d . . . O3 O 0.45486(5) 0.78314(12) 0.01959(6) 0.0216(2) Uani 1 1 d . . . C3 C 0.32616(7) 0.91139(15) 0.02509(8) 0.0172(3) Uani 1 1 d . . . N3 N 0.38071(7) 0.92935(15) -0.11163(7) 0.0198(2) Uani 1 1 d . . . H3N H 0.3361(11) 0.986(2) -0.1370(12) 0.033(4) Uiso 1 1 d . . . C4 C 0.19920(8) 1.03892(16) 0.01123(9) 0.0188(3) Uani 1 1 d . . . C5 C 0.12507(8) 1.13428(18) -0.04615(11) 0.0249(3) Uani 1 1 d . . . H5C H 0.0741(10) 1.063(2) -0.0555(11) 0.030(4) Uiso 1 1 d . . . H5B H 0.1357(11) 1.160(2) -0.1062(13) 0.038(5) Uiso 1 1 d . . . H5A H 0.1133(11) 1.236(2) -0.0142(13) 0.037(5) Uiso 1 1 d . . . C6 C 0.39285(7) 0.86956(15) -0.02300(9) 0.0172(3) Uani 1 1 d . . . C7 C 0.13080(9) 1.0365(2) 0.14466(11) 0.0254(3) Uani 1 1 d . . . H7C H 0.0824(12) 0.981(3) 0.1084(14) 0.044(5) Uiso 1 1 d . . . H7B H 0.1247(12) 1.158(3) 0.1442(13) 0.048(5) Uiso 1 1 d . . . H7A H 0.1426(12) 0.998(3) 0.2105(15) 0.056(6) Uiso 1 1 d . . . C8 C 0.43931(9) 0.9051(2) -0.16934(10) 0.0252(3) Uani 1 1 d . . . H8C H 0.4893(13) 0.862(3) -0.1308(14) 0.051(6) Uiso 1 1 d . . . H8B H 0.4166(13) 0.824(3) -0.2219(14) 0.052(6) Uiso 1 1 d . . . H8A H 0.4508(12) 1.011(3) -0.1961(13) 0.045(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0158(5) 0.0208(5) 0.0214(5) -0.0043(4) 0.0069(4) -0.0016(4) O1 0.0259(5) 0.0318(5) 0.0190(5) -0.0013(4) 0.0080(4) -0.0021(4) C1 0.0194(6) 0.0192(6) 0.0193(6) -0.0038(5) 0.0050(5) -0.0029(5) O2 0.0198(5) 0.0258(5) 0.0195(4) 0.0027(4) 0.0044(4) 0.0033(4) C2 0.0164(6) 0.0173(6) 0.0194(6) -0.0020(5) 0.0032(4) -0.0012(4) N2 0.0159(5) 0.0183(5) 0.0209(5) 0.0000(4) 0.0046(4) 0.0000(4) O3 0.0190(4) 0.0242(5) 0.0219(5) 0.0012(4) 0.0057(3) 0.0046(4) C3 0.0162(6) 0.0159(6) 0.0194(6) -0.0025(4) 0.0045(4) -0.0016(4) N3 0.0173(5) 0.0240(6) 0.0190(5) 0.0019(4) 0.0062(4) 0.0024(4) C4 0.0176(6) 0.0162(6) 0.0226(6) -0.0029(5) 0.0050(5) -0.0020(5) C5 0.0187(6) 0.0235(7) 0.0318(8) 0.0020(6) 0.0054(5) 0.0042(5) C6 0.0165(6) 0.0163(6) 0.0190(6) -0.0021(4) 0.0049(4) -0.0015(4) C7 0.0204(6) 0.0294(7) 0.0296(7) -0.0071(6) 0.0119(5) 0.0003(5) C8 0.0260(7) 0.0309(7) 0.0220(6) 0.0014(6) 0.0122(5) 0.0024(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.3798(16) . ? N1 C1 1.3965(16) . ? N1 C7 1.4729(16) . ? O1 C1 1.2259(15) . ? C1 C2 1.4549(17) . ? O2 C2 1.3463(15) . ? C2 C3 1.3634(17) . ? N2 C4 1.2962(16) . ? N2 C3 1.3740(15) . ? O3 C6 1.2504(15) . ? C3 C6 1.4878(16) . ? N3 C6 1.3256(16) . ? N3 C8 1.4478(16) . ? C4 C5 1.4913(18) . ? 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 C4 N1 C1 122.49(10) . . ? C4 N1 C7 120.34(11) . . ? C1 N1 C7 117.16(11) . . ? O1 C1 N1 121.99(11) . . ? O1 C1 C2 124.07(12) . . ? N1 C1 C2 113.94(10) . . ? O2 C2 C3 124.40(11) . . ? O2 C2 C1 116.15(11) . . ? C3 C2 C1 119.46(11) . . ? C4 N2 C3 118.30(11) . . ? C2 C3 N2 123.10(11) . . ? C2 C3 C6 120.24(11) . . ? N2 C3 C6 116.65(10) . . ? C6 N3 C8 123.46(11) . . ? N2 C4 N1 122.70(11) . . ? N2 C4 C5 118.95(11) . . ? N1 C4 C5 118.34(11) . . ? O3 C6 N3 124.24(11) . . ? O3 C6 C3 120.49(11) . . ? N3 C6 C3 115.26(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 O1 179.59(11) . . . . ? C7 N1 C1 O1 -0.22(18) . . . . ? C4 N1 C1 C2 -0.44(17) . . . . ? C7 N1 C1 C2 179.76(11) . . . . ? O1 C1 C2 O2 0.79(19) . . . . ? N1 C1 C2 O2 -179.19(10) . . . . ? O1 C1 C2 C3 -179.20(11) . . . . ? N1 C1 C2 C3 0.83(17) . . . . ? O2 C2 C3 N2 179.50(11) . . . . ? C1 C2 C3 N2 -0.51(19) . . . . ? O2 C2 C3 C6 0.49(19) . . . . ? C1 C2 C3 C6 -179.52(10) . . . . ? C4 N2 C3 C2 -0.29(18) . . . . ? C4 N2 C3 C6 178.75(10) . . . . ? C3 N2 C4 N1 0.73(18) . . . . ? C3 N2 C4 C5 -178.43(11) . . . . ? C1 N1 C4 N2 -0.35(19) . . . . ? C7 N1 C4 N2 179.45(11) . . . . ? C1 N1 C4 C5 178.81(11) . . . . ? C7 N1 C4 C5 -1.39(17) . . . . ? C8 N3 C6 O3 -1.6(2) . . . . ? C8 N3 C6 C3 178.69(11) . . . . ? C2 C3 C6 O3 0.77(18) . . . . ? N2 C3 C6 O3 -178.30(10) . . . . ? C2 C3 C6 N3 -179.51(11) . . . . ? N2 C3 C6 N3 1.42(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O3 0.91(2) 1.76(2) 2.5918(13) 151.2(19) . N3 H3N O1 0.859(18) 2.172(18) 2.9345(15) 147.8(15) 6_575 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 926547'