# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_Compound1 _database_code_depnum_ccdc_archive 'CCDC 922744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2 O2' _chemical_formula_sum 'C6 H10 N2 O2' _chemical_formula_weight 142.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7744(3) _cell_length_b 15.2403(8) _cell_length_c 7.9988(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.736(4) _cell_angle_gamma 90.00 _cell_volume 703.12(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1089 _cell_measurement_theta_min 5.8065 _cell_measurement_theta_max 73.2166 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3652 _exptl_crystal_size_mid 0.1333 _exptl_crystal_size_min 0.0515 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_T_min 0.846 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5953 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2438 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 5.81 _diffrn_reflns_theta_max 72.00 _reflns_number_total 1356 _reflns_number_gt 1177 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0698P)^2^+0.1121P] 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 1356 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 C1 C 0.0419(2) 0.93641(9) 0.81828(17) 0.0368(3) Uani 1 1 d . . . C2 C 0.2782(2) 0.93319(9) 0.84301(19) 0.0412(4) Uani 1 1 d . . . H3 H 0.3833 0.9730 0.8018 0.049 Uiso 1 1 calc R . . C3 C 0.3340(2) 0.85885(9) 0.94195(18) 0.0373(3) Uani 1 1 d . . . C4 C 0.0826(2) 0.73943(9) 1.06059(18) 0.0388(3) Uani 1 1 d . . . H4A H -0.0229 0.7511 1.1487 0.047 Uiso 1 1 calc R . . H4B H 0.2268 0.7180 1.1127 0.047 Uiso 1 1 calc R . . C5 C -0.0202(3) 0.66915(10) 0.9471(2) 0.0468(4) Uani 1 1 d . . . H5A H -0.0663 0.6195 1.0138 0.056 Uiso 1 1 calc R . . H5B H -0.1574 0.6918 0.8872 0.056 Uiso 1 1 calc R . . C6 C -0.1067(3) 1.00119(11) 0.7248(2) 0.0484(4) Uani 1 1 d . . . H6A H -0.1768 0.9738 0.6268 0.073 Uiso 1 1 calc R . . H6B H -0.0137 1.0499 0.6921 0.073 Uiso 1 1 calc R . . H6C H -0.2257 1.0217 0.7950 0.073 Uiso 1 1 calc R . . N1 N 0.12704(18) 0.82043(7) 0.97365(15) 0.0362(3) Uani 1 1 d . . . N2 N -0.0500(2) 0.86703(7) 0.89490(15) 0.0373(3) Uani 1 1 d . . . H1 H -0.204(3) 0.8587(12) 0.924(2) 0.050(5) Uiso 1 1 d . . . O1 O 0.52667(16) 0.82757(8) 0.99928(14) 0.0485(3) Uani 1 1 d . . . O2 O 0.1412(3) 0.64121(10) 0.8313(2) 0.0707(4) Uani 1 1 d . . . H2 H 0.092(5) 0.658(2) 0.731(4) 0.111(10) 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 C1 0.0354(7) 0.0354(7) 0.0404(7) -0.0011(5) 0.0107(5) -0.0010(5) C2 0.0327(7) 0.0428(7) 0.0490(8) 0.0005(6) 0.0122(6) -0.0066(5) C3 0.0259(7) 0.0441(8) 0.0427(7) -0.0053(6) 0.0090(5) -0.0023(5) C4 0.0363(7) 0.0427(7) 0.0376(7) 0.0050(6) 0.0058(5) -0.0004(6) C5 0.0480(9) 0.0387(7) 0.0532(9) 0.0049(7) -0.0012(7) -0.0015(6) C6 0.0428(8) 0.0451(8) 0.0579(9) 0.0081(7) 0.0083(7) 0.0022(6) N1 0.0248(6) 0.0369(6) 0.0474(7) 0.0025(5) 0.0067(4) -0.0005(4) N2 0.0253(6) 0.0386(6) 0.0483(7) 0.0039(5) 0.0064(5) 0.0000(4) O1 0.0251(5) 0.0634(7) 0.0574(6) 0.0084(5) 0.0058(4) -0.0005(4) O2 0.0750(9) 0.0753(9) 0.0610(8) -0.0197(7) -0.0036(7) 0.0312(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.3442(18) . ? C1 C2 1.370(2) . ? C1 C6 1.487(2) . ? C2 C3 1.411(2) . ? C3 O1 1.2751(17) . ? C3 N1 1.3656(17) . ? C4 N1 1.4459(18) . ? C4 C5 1.507(2) . ? C5 O2 1.411(2) . ? N1 N2 1.3729(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 N2 C1 C2 108.56(12) . . ? N2 C1 C6 121.37(12) . . ? C2 C1 C6 130.07(13) . . ? C1 C2 C3 108.01(12) . . ? O1 C3 N1 121.95(13) . . ? O1 C3 C2 132.39(13) . . ? N1 C3 C2 105.66(12) . . ? N1 C4 C5 113.00(12) . . ? O2 C5 C4 110.89(13) . . ? C3 N1 N2 109.41(11) . . ? C3 N1 C4 129.23(12) . . ? N2 N1 C4 121.12(10) . . ? C1 N2 N1 108.33(11) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 73.22 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.152 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.052 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 922745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H9 N3 O3' _chemical_formula_sum 'C6 H9 N3 O3' _chemical_formula_weight 171.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.298(2) _cell_length_b 15.1999(5) _cell_length_c 12.458(3) _cell_angle_alpha 90.00 _cell_angle_beta 149.966(3) _cell_angle_gamma 90.00 _cell_volume 786.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1590 _cell_measurement_theta_min 2.8420 _cell_measurement_theta_max 73.2430 _exptl_crystal_description prism _exptl_crystal_colour 'dark yellow' _exptl_crystal_size_max 0.2638 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0755 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 1.043 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5953 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2580 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.82 _diffrn_reflns_theta_max 67.04 _reflns_number_total 1392 _reflns_number_gt 1274 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0711P)^2^+0.3321P] 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 1392 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 C1 C 1.1450(4) 0.18454(12) 0.9543(3) 0.0362(4) Uani 1 1 d . . . C2 C 1.0316(4) 0.26804(11) 0.9322(3) 0.0331(4) Uani 1 1 d . . . C3 C 0.8190(4) 0.24310(11) 0.9017(3) 0.0320(4) Uani 1 1 d . . . C4 C 0.6697(5) 0.09559(12) 0.8898(3) 0.0397(4) Uani 1 1 d . . . H6A H 0.6967 0.1182 0.9776 0.048 Uiso 1 1 calc R . . H6B H 0.7725 0.0383 0.9458 0.048 Uiso 1 1 calc R . . C5 C 0.3157(5) 0.08515(12) 0.6625(3) 0.0422(5) Uani 1 1 d . . . H7A H 0.2215 0.0464 0.6615 0.051 Uiso 1 1 calc R . . H7B H 0.2113 0.1420 0.6086 0.051 Uiso 1 1 calc R . . C6 C 1.3705(5) 0.17028(16) 0.9930(4) 0.0530(5) Uani 1 1 d . . . H12A H 1.5808 0.1911 1.1336 0.079 Uiso 1 1 calc R . . H12B H 1.2948 0.2019 0.8876 0.079 Uiso 1 1 calc R . . H12C H 1.3811 0.1086 0.9828 0.079 Uiso 1 1 calc R . . H3 H 1.078(8) 0.467(3) 0.927(6) 0.110(12) Uiso 1 1 d . . . H2 H 0.250(7) 0.096(2) 0.480(5) 0.073(8) Uiso 1 1 d . . . N1 N 0.8276(3) 0.15448(9) 0.9058(2) 0.0343(4) Uani 1 1 d . . . N2 N 1.0231(3) 0.11945(10) 0.9368(2) 0.0373(4) Uani 1 1 d . . . N3 N 1.1160(4) 0.34324(10) 0.9414(2) 0.0415(4) Uani 1 1 d . . . O1 O 0.6681(3) 0.28876(8) 0.8786(2) 0.0425(4) Uani 1 1 d . . . O2 O 0.2556(3) 0.05024(8) 0.5236(2) 0.0430(4) Uani 1 1 d . . . O3 O 0.9831(4) 0.41172(9) 0.9171(2) 0.0477(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0347(8) 0.0361(9) 0.0379(9) -0.0003(7) 0.0314(8) -0.0006(7) C2 0.0318(8) 0.0305(9) 0.0313(8) -0.0010(6) 0.0265(7) -0.0031(6) C3 0.0313(8) 0.0274(8) 0.0315(8) -0.0025(6) 0.0263(8) -0.0016(6) C4 0.0508(10) 0.0302(9) 0.0558(11) -0.0008(7) 0.0487(10) -0.0028(7) C5 0.0492(10) 0.0331(9) 0.0614(11) -0.0065(8) 0.0504(10) -0.0055(8) C6 0.0536(11) 0.0551(12) 0.0678(13) 0.0021(10) 0.0551(12) 0.0033(10) N1 0.0379(8) 0.0261(7) 0.0458(8) -0.0011(6) 0.0372(7) -0.0009(6) N2 0.0404(8) 0.0320(8) 0.0460(8) 0.0003(6) 0.0383(7) 0.0020(6) N3 0.0429(8) 0.0364(9) 0.0378(8) 0.0001(6) 0.0339(7) -0.0016(6) O1 0.0483(7) 0.0314(6) 0.0564(8) -0.0035(5) 0.0465(7) -0.0002(5) O2 0.0556(8) 0.0263(6) 0.0572(8) -0.0038(6) 0.0503(8) -0.0040(6) O3 0.0586(8) 0.0345(7) 0.0615(9) -0.0006(6) 0.0536(8) -0.0019(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 C1 N2 1.292(2) . ? C1 C2 1.457(2) . ? C1 C6 1.489(3) . ? C2 N3 1.293(2) . ? C2 C3 1.497(2) . ? C3 O1 1.228(2) . ? C3 N1 1.348(2) . ? C4 N1 1.451(2) . ? C4 C5 1.507(3) . ? C5 O2 1.426(2) . ? N1 N2 1.406(2) . ? N3 O3 1.347(2) . ? 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 N2 C1 C2 110.61(15) . . ? N2 C1 C6 121.61(17) . . ? C2 C1 C6 127.78(17) . . ? N3 C2 C1 122.82(16) . . ? N3 C2 C3 132.48(16) . . ? C1 C2 C3 104.70(14) . . ? O1 C3 N1 125.71(16) . . ? O1 C3 C2 130.93(16) . . ? N1 C3 C2 103.37(14) . . ? N1 C4 C5 112.53(15) . . ? O2 C5 C4 112.55(15) . . ? C3 N1 N2 113.56(13) . . ? C3 N1 C4 126.83(14) . . ? N2 N1 C4 119.57(14) . . ? C1 N2 N1 107.75(14) . . ? C2 N3 O3 112.85(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.504 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.048 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 922746' #TrackingRef '17374_web_deposit_cif_file_2_PauDiazGallifa_1359636207.compound4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O3' _chemical_formula_sum 'C11 H11 N3 O3' _chemical_formula_weight 233.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.8072(7) _cell_length_b 4.92528(15) _cell_length_c 16.3792(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.696(5) _cell_angle_gamma 90.00 _cell_volume 1139.26(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2756 _cell_measurement_theta_min 5.2396 _cell_measurement_theta_max 70.1159 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.5402 _exptl_crystal_size_mid 0.0831 _exptl_crystal_size_min 0.0413 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_T_min 0.811 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5953 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5877 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.24 _diffrn_reflns_theta_max 70.11 _reflns_number_total 2105 _reflns_number_gt 1626 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0333P)^2^+0.5913P] 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 2105 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.220 _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 C1 C 0.95483(17) 0.3757(5) 0.19585(17) 0.0481(6) Uani 1 1 d . . . C2 C 0.95411(16) 0.2305(5) 0.27329(15) 0.0444(5) Uani 1 1 d . . . C3 C 0.87464(16) 0.0328(5) 0.23193(15) 0.0456(6) Uani 1 1 d . . . C4 C 0.76036(18) -0.0567(6) 0.06822(16) 0.0519(6) Uani 1 1 d . . . H4A H 0.7751 -0.2486 0.0708 0.062 Uiso 1 1 calc R . . H4B H 0.7527 0.0126 0.0099 0.062 Uiso 1 1 calc R . . C5 C 0.66915(17) -0.0218(6) 0.07434(17) 0.0528(6) Uani 1 1 d . . . H5A H 0.6194 -0.1235 0.0257 0.063 Uiso 1 1 calc R . . H5B H 0.6761 -0.0925 0.1323 0.063 Uiso 1 1 calc R . . C6 C 1.02137(19) 0.5831(5) 0.1950(2) 0.0560(7) Uani 1 1 d . . . C7 C 1.0841(2) 0.7150(6) 0.2729(3) 0.0678(8) Uani 1 1 d . . . H7 H 1.0850(2) 0.6731(16) 0.332(2) 0.081 Uiso 1 1 calc R . . C8 C 1.1460(2) 0.9068(7) 0.2683(3) 0.0844(11) Uani 1 1 d . . . H8 H 1.1872(18) 0.996(4) 0.321(2) 0.101 Uiso 1 1 calc R . . C9 C 1.1466(3) 0.9643(8) 0.1873(4) 0.0971(13) Uani 1 1 d . . . H9 H 1.190(2) 1.093(6) 0.1849(4) 0.116 Uiso 1 1 calc R . . C10 C 1.0847(3) 0.8353(10) 0.1095(4) 0.1062(14) Uani 1 1 d . . . H10 H 1.0849(3) 0.876(2) 0.052(3) 0.127 Uiso 1 1 calc R . . C11 C 1.0218(3) 0.6471(8) 0.1129(3) 0.0853(11) Uani 1 1 d . . . H11 H 0.9776(17) 0.559(4) 0.057(2) 0.102 Uiso 1 1 calc R . . N1 N 0.83890(14) 0.0836(4) 0.14145(13) 0.0481(5) Uani 1 1 d . . . N2 N 0.88721(15) 0.2864(5) 0.12011(14) 0.0508(5) Uani 1 1 d . . . N3 N 1.01599(14) 0.2646(4) 0.35742(14) 0.0500(5) Uani 1 1 d . . . O1 O 0.84563(13) -0.1413(4) 0.26644(11) 0.0581(5) Uani 1 1 d . . . O2 O 0.64382(13) 0.2576(4) 0.06683(12) 0.0586(5) Uani 1 1 d . . . H2 H 0.641(3) 0.306(8) 0.117(3) 0.097(12) Uiso 1 1 d . . . O3 O 1.00334(13) 0.0937(4) 0.41613(12) 0.0573(5) Uani 1 1 d . . . H3 H 1.051(2) 0.142(7) 0.470(2) 0.076(10) 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 C1 0.0474(13) 0.0486(14) 0.0509(14) 0.0067(11) 0.0243(12) 0.0077(11) C2 0.0407(12) 0.0469(13) 0.0427(13) 0.0036(10) 0.0161(11) 0.0043(10) C3 0.0406(12) 0.0532(14) 0.0382(12) 0.0052(11) 0.0135(10) 0.0039(11) C4 0.0535(14) 0.0553(15) 0.0395(12) -0.0022(11) 0.0142(11) 0.0067(12) C5 0.0479(14) 0.0587(16) 0.0424(13) -0.0018(11) 0.0118(11) -0.0034(12) C6 0.0511(14) 0.0494(15) 0.0724(18) 0.0107(13) 0.0322(14) 0.0079(12) C7 0.0621(17) 0.0556(17) 0.091(2) 0.0005(16) 0.0389(17) -0.0010(14) C8 0.064(2) 0.062(2) 0.126(3) -0.002(2) 0.041(2) -0.0057(16) C9 0.077(2) 0.074(2) 0.156(4) 0.027(3) 0.066(3) -0.0036(19) C10 0.100(3) 0.117(3) 0.120(3) 0.034(3) 0.066(3) -0.015(3) C11 0.085(2) 0.096(3) 0.084(2) 0.017(2) 0.047(2) -0.016(2) N1 0.0451(11) 0.0575(13) 0.0384(10) 0.0059(9) 0.0159(9) 0.0015(9) N2 0.0493(12) 0.0579(13) 0.0471(12) 0.0105(10) 0.0234(10) 0.0069(10) N3 0.0478(12) 0.0524(12) 0.0484(12) 0.0039(10) 0.0205(10) 0.0011(10) O1 0.0570(11) 0.0660(12) 0.0425(9) 0.0084(8) 0.0145(8) -0.0125(9) O2 0.0550(11) 0.0699(13) 0.0395(9) -0.0028(9) 0.0111(8) 0.0179(9) O3 0.0505(10) 0.0696(12) 0.0394(9) 0.0053(9) 0.0092(8) -0.0105(9) _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 C1 N2 1.298(3) . ? C1 C2 1.461(3) . ? C1 C6 1.471(4) . ? C2 N3 1.293(3) . ? C2 C3 1.490(3) . ? C3 O1 1.224(3) . ? C3 N1 1.351(3) . ? C4 N1 1.456(3) . ? C4 C5 1.499(4) . ? C5 O2 1.423(3) . ? C6 C7 1.378(4) . ? C6 C11 1.384(4) . ? C7 C8 1.387(4) . ? C8 C9 1.359(6) . ? C9 C10 1.366(6) . ? C10 C11 1.378(5) . ? N1 N2 1.394(3) . ? N3 O3 1.359(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 N2 C1 C2 109.9(2) . . ? N2 C1 C6 120.8(2) . . ? C2 C1 C6 129.3(2) . . ? N3 C2 C1 124.4(2) . . ? N3 C2 C3 130.5(2) . . ? C1 C2 C3 105.0(2) . . ? O1 C3 N1 125.3(2) . . ? O1 C3 C2 131.5(2) . . ? N1 C3 C2 103.3(2) . . ? N1 C4 C5 112.4(2) . . ? O2 C5 C4 110.3(2) . . ? C7 C6 C11 118.5(3) . . ? C7 C6 C1 122.6(3) . . ? C11 C6 C1 118.9(3) . . ? C6 C7 C8 120.1(3) . . ? C9 C8 C7 120.6(4) . . ? C8 C9 C10 119.8(4) . . ? C9 C10 C11 120.2(4) . . ? C10 C11 C6 120.7(4) . . ? C3 N1 N2 113.7(2) . . ? C3 N1 C4 126.7(2) . . ? N2 N1 C4 119.60(18) . . ? C1 N2 N1 108.18(19) . . ? C2 N3 O3 113.1(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 70.11 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.141 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.034