# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email nonappa@jyu.fi _publ_contact_author_name 'Nonappa ' loop_ _publ_author_name Nonappa 'Kari Ahonen' 'Manu Lahtinen' 'Erkki Kolehmainen' # Attachment '- Compound 9.cif' data_xsodu173-2 _database_code_depnum_ccdc_archive 'CCDC 783550' #TrackingRef '- Compound 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C10 H14 N2 O4), 2(H2 O)' _chemical_formula_sum 'C10 H18 N2 O6' _chemical_formula_weight 262.26 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_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 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 7.7534(16) _cell_length_b 8.0651(16) _cell_length_c 18.818(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1176.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 22932 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7301 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details 'SADABS (Sheldrick, G. M., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Kappa APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9344 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2893 _reflns_number_gt 2432 _reflns_threshold_expression >2\s(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS97 or SIR2002' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0335P)^2^+0.2208P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(11) _chemical_absolute_configuration syn _refine_ls_number_reflns 2893 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 H3H H 0.229(4) 0.797(4) 1.1143(15) 0.063(10) Uiso 1 1 d . . . H4H H 0.369(4) 0.025(4) 0.7681(14) 0.056(9) Uiso 1 1 d . . . H5AW H 0.733(4) 0.412(4) 0.8494(18) 0.077(10) Uiso 1 1 d . . . H5BW H 0.704(3) 0.421(3) 0.9239(14) 0.046(7) Uiso 1 1 d . . . H6AW H 0.723(4) 0.262(3) 0.7233(16) 0.065(9) Uiso 1 1 d . . . H6BW H 0.567(4) 0.257(3) 0.7622(14) 0.054(9) Uiso 1 1 d . . . C1 C 0.1734(2) 0.5806(2) 0.88774(9) 0.0163(4) Uani 1 1 d . . . C3 C 0.1647(2) 0.4387(2) 1.00453(8) 0.0163(4) Uani 1 1 d . . . H3 H 0.2844 0.4334 1.0242 0.020 Uiso 1 1 calc R . . C4 C 0.1245(2) 0.2780(2) 0.96653(9) 0.0178(4) Uani 1 1 d . . . C6 C 0.2363(2) 0.4161(2) 0.85884(9) 0.0166(4) Uani 1 1 d . . . H6 H 0.3645 0.4099 0.8642 0.020 Uiso 1 1 calc R . . C7 C 0.0774(3) 0.7291(2) 0.99511(10) 0.0197(4) Uani 1 1 d . . . H7A H -0.0369 0.7599 0.9757 0.024 Uiso 1 1 calc R . . H7B H 0.1556 0.8258 0.9918 0.024 Uiso 1 1 calc R . . C8 C 0.0625(3) 0.6674(3) 1.07191(10) 0.0225(4) Uani 1 1 d . . . H8 H -0.0381 0.7191 1.0967 0.027 Uiso 1 1 calc R . . C9 C 0.0391(3) 0.4817(2) 1.06410(10) 0.0233(4) Uani 1 1 d . . . H9A H -0.0810 0.4538 1.0507 0.028 Uiso 1 1 calc R . . H9B H 0.0692 0.4230 1.1086 0.028 Uiso 1 1 calc R . . C10 C 0.1065(3) 0.1411(2) 0.84889(9) 0.0211(4) Uani 1 1 d . . . H10A H -0.0205 0.1336 0.8445 0.025 Uiso 1 1 calc R . . H10B H 0.1520 0.0332 0.8655 0.025 Uiso 1 1 calc R . . C11 C 0.1892(2) 0.1920(2) 0.77853(9) 0.0189(4) Uani 1 1 d . . . H11 H 0.1214 0.1504 0.7370 0.023 Uiso 1 1 calc R . . C12 C 0.1888(3) 0.3807(2) 0.78184(9) 0.0202(4) Uani 1 1 d . . . H12A H 0.2750 0.4284 0.7488 0.024 Uiso 1 1 calc R . . H12B H 0.0736 0.4259 0.7701 0.024 Uiso 1 1 calc R . . N2 N 0.14934(19) 0.58491(18) 0.95749(7) 0.0162(3) Uani 1 1 d . . . N5 N 0.1568(2) 0.27613(18) 0.89719(8) 0.0172(3) Uani 1 1 d . . . O1 O 0.15133(18) 0.70344(16) 0.84896(6) 0.0208(3) Uani 1 1 d . . . O2 O 0.06632(18) 0.15668(16) 0.99924(7) 0.0218(3) Uani 1 1 d . . . O3 O 0.21834(19) 0.6928(2) 1.11044(7) 0.0275(3) Uani 1 1 d . . . O4 O 0.36452(18) 0.13766(18) 0.77559(7) 0.0219(3) Uani 1 1 d . . . O6W O 0.6615(2) 0.31278(18) 0.76117(7) 0.0248(3) Uani 1 1 d . . . O5W O 0.7656(2) 0.46213(18) 0.88833(8) 0.0295(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 0.0141(9) 0.0168(9) 0.0179(8) -0.0008(7) 0.0018(7) -0.0007(8) C3 0.0166(9) 0.0171(9) 0.0151(8) 0.0019(7) 0.0012(7) -0.0010(8) C4 0.0125(9) 0.0198(10) 0.0209(9) 0.0006(7) 0.0001(7) 0.0007(8) C6 0.0166(9) 0.0153(9) 0.0177(8) -0.0003(7) 0.0011(7) -0.0001(8) C7 0.0208(10) 0.0185(10) 0.0198(9) -0.0036(7) -0.0003(8) 0.0036(8) C8 0.0230(10) 0.0254(11) 0.0190(9) -0.0036(8) 0.0036(8) 0.0030(9) C9 0.0250(10) 0.0254(11) 0.0194(9) -0.0014(8) 0.0082(8) -0.0028(8) C10 0.0234(10) 0.0170(9) 0.0227(9) -0.0043(7) -0.0003(8) -0.0026(8) C11 0.0174(9) 0.0203(10) 0.0189(9) -0.0028(8) -0.0012(7) 0.0014(8) C12 0.0260(10) 0.0179(10) 0.0168(8) -0.0004(7) -0.0012(7) 0.0021(8) N2 0.0177(7) 0.0136(7) 0.0174(7) -0.0003(6) 0.0012(6) 0.0004(7) N5 0.0213(8) 0.0129(7) 0.0174(7) -0.0006(6) -0.0002(6) -0.0010(7) O1 0.0243(7) 0.0182(6) 0.0198(6) 0.0021(5) 0.0014(5) 0.0012(6) O2 0.0265(7) 0.0162(7) 0.0226(7) 0.0028(6) 0.0009(6) -0.0040(6) O3 0.0345(8) 0.0262(8) 0.0218(7) -0.0045(6) -0.0064(6) -0.0004(7) O4 0.0205(7) 0.0175(7) 0.0277(7) -0.0030(6) 0.0026(5) 0.0017(6) O6W 0.0287(8) 0.0202(8) 0.0256(7) -0.0045(6) 0.0069(6) -0.0043(7) O5W 0.0370(9) 0.0272(9) 0.0242(8) 0.0000(6) 0.0025(7) -0.0033(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.242(2) . ? C1 N2 1.326(2) . ? C1 C6 1.515(2) . ? C3 N2 1.479(2) . ? C3 C4 1.513(3) . ? C3 C9 1.525(3) . ? C3 H3 1.0000 . ? C4 O2 1.241(2) . ? C4 N5 1.329(2) . ? C6 N5 1.475(2) . ? C6 C12 1.522(2) . ? C6 H6 1.0000 . ? C7 N2 1.471(2) . ? C7 C8 1.533(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O3 1.424(2) . ? C8 C9 1.516(3) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N5 1.471(2) . ? C10 C11 1.527(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O4 1.429(2) . ? C11 C12 1.523(3) . ? C11 H11 1.0000 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? O3 H3H 0.85(3) . ? O4 H4H 0.92(3) . ? O6W H6AW 0.95(3) . ? O6W H6BW 0.86(3) . ? O5W H5AW 0.87(3) . ? O5W H5BW 0.89(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 O1 C1 N2 122.78(17) . . ? O1 C1 C6 122.13(15) . . ? N2 C1 C6 115.05(15) . . ? N2 C3 C4 112.55(13) . . ? N2 C3 C9 101.93(14) . . ? C4 C3 C9 114.25(15) . . ? N2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C9 C3 H3 109.3 . . ? O2 C4 N5 123.14(18) . . ? O2 C4 C3 121.07(15) . . ? N5 C4 C3 115.79(15) . . ? N5 C6 C1 111.11(14) . . ? N5 C6 C12 102.77(14) . . ? C1 C6 C12 115.36(14) . . ? N5 C6 H6 109.1 . . ? C1 C6 H6 109.1 . . ? C12 C6 H6 109.1 . . ? N2 C7 C8 103.06(15) . . ? N2 C7 H7A 111.2 . . ? C8 C7 H7A 111.2 . . ? N2 C7 H7B 111.2 . . ? C8 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? O3 C8 C9 107.05(17) . . ? O3 C8 C7 111.65(16) . . ? C9 C8 C7 103.78(15) . . ? O3 C8 H8 111.3 . . ? C9 C8 H8 111.3 . . ? C7 C8 H8 111.3 . . ? C8 C9 C3 102.69(16) . . ? C8 C9 H9A 111.2 . . ? C3 C9 H9A 111.2 . . ? C8 C9 H9B 111.2 . . ? C3 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? N5 C10 C11 103.01(15) . . ? N5 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? N5 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? O4 C11 C12 108.07(15) . . ? O4 C11 C10 110.51(15) . . ? C12 C11 C10 103.44(14) . . ? O4 C11 H11 111.5 . . ? C12 C11 H11 111.5 . . ? C10 C11 H11 111.5 . . ? C6 C12 C11 103.06(14) . . ? C6 C12 H12A 111.2 . . ? C11 C12 H12A 111.2 . . ? C6 C12 H12B 111.2 . . ? C11 C12 H12B 111.2 . . ? H12A C12 H12B 109.1 . . ? C1 N2 C7 123.38(15) . . ? C1 N2 C3 124.06(15) . . ? C7 N2 C3 111.88(13) . . ? C4 N5 C10 124.42(16) . . ? C4 N5 C6 123.41(15) . . ? C10 N5 C6 112.03(14) . . ? C8 O3 H3H 106(2) . . ? C11 O4 H4H 110.1(19) . . ? H6AW O6W H6BW 103(3) . . ? H5AW O5W H5BW 108(3) . . ? 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 N2 C3 C4 O2 -151.93(16) . . . . ? C9 C3 C4 O2 -36.3(2) . . . . ? N2 C3 C4 N5 28.6(2) . . . . ? C9 C3 C4 N5 144.20(17) . . . . ? O1 C1 C6 N5 -145.19(17) . . . . ? N2 C1 C6 N5 36.9(2) . . . . ? O1 C1 C6 C12 -28.8(2) . . . . ? N2 C1 C6 C12 153.35(16) . . . . ? N2 C7 C8 O3 87.07(18) . . . . ? N2 C7 C8 C9 -27.9(2) . . . . ? O3 C8 C9 C3 -77.64(18) . . . . ? C7 C8 C9 C3 40.57(19) . . . . ? N2 C3 C9 C8 -36.69(18) . . . . ? C4 C3 C9 C8 -158.37(15) . . . . ? N5 C10 C11 O4 84.98(18) . . . . ? N5 C10 C11 C12 -30.48(18) . . . . ? N5 C6 C12 C11 -33.33(18) . . . . ? C1 C6 C12 C11 -154.40(15) . . . . ? O4 C11 C12 C6 -77.17(17) . . . . ? C10 C11 C12 C6 40.02(18) . . . . ? O1 C1 N2 C7 6.5(3) . . . . ? C6 C1 N2 C7 -175.62(16) . . . . ? O1 C1 N2 C3 176.32(16) . . . . ? C6 C1 N2 C3 -5.8(2) . . . . ? C8 C7 N2 C1 175.60(16) . . . . ? C8 C7 N2 C3 4.7(2) . . . . ? C4 C3 N2 C1 -27.9(2) . . . . ? C9 C3 N2 C1 -150.78(17) . . . . ? C4 C3 N2 C7 142.91(16) . . . . ? C9 C3 N2 C7 20.07(19) . . . . ? O2 C4 N5 C10 8.8(3) . . . . ? C3 C4 N5 C10 -171.72(16) . . . . ? O2 C4 N5 C6 -175.94(17) . . . . ? C3 C4 N5 C6 3.6(3) . . . . ? C11 C10 N5 C4 -174.44(17) . . . . ? C11 C10 N5 C6 9.8(2) . . . . ? C1 C6 N5 C4 -37.1(2) . . . . ? C12 C6 N5 C4 -161.01(17) . . . . ? C1 C6 N5 C10 138.72(16) . . . . ? C12 C6 N5 C10 14.79(19) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.047 data_xsodu176-new _database_code_depnum_ccdc_archive 'CCDC 783551' #TrackingRef '- Ccompound11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N2 O2' _chemical_formula_sum 'C18 H14 N2 O2' _chemical_formula_weight 290.31 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 10.5612(14) _cell_length_b 8.4166(5) _cell_length_c 15.8706(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.860(4) _cell_angle_gamma 90.00 _cell_volume 1342.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6317 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _exptl_crystal_description plate _exptl_crystal_colour 'light orange' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6252 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS (Sheldrick, G. M., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Kappa APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7809 _diffrn_reflns_av_R_equivalents 0.1095 _diffrn_reflns_av_sigmaI/netI 0.1402 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2627 _reflns_number_gt 1322 _reflns_threshold_expression >2\s(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS97 or SIR2002' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0000P)^2^+1.7740P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2627 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1714 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.1447 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.5078(4) 1.3622(4) 0.8660(2) 0.0237(9) Uani 1 1 d . . . C3 C 0.6060(4) 1.1539(4) 0.7954(2) 0.0231(9) Uani 1 1 d . . . H3 H 0.5466 1.1644 0.7330 0.028 Uiso 1 1 calc R . . C4 C 0.5497(4) 1.0254(4) 0.8402(2) 0.0203(9) Uani 1 1 d . . . C6 C 0.3957(4) 1.2422(4) 0.8495(3) 0.0225(9) Uani 1 1 d . . . H6 H 0.3399 1.2501 0.7861 0.027 Uiso 1 1 calc R . . C7 C 0.7282(4) 1.3921(4) 0.8415(2) 0.0212(9) Uani 1 1 d . . . C8 C 0.7617(4) 1.5486(4) 0.8657(3) 0.0269(10) Uani 1 1 d . . . H8 H 0.7049 1.6158 0.8860 0.032 Uiso 1 1 calc R . . C9 C 0.8820(4) 1.6021(4) 0.8588(3) 0.0315(10) Uani 1 1 d . . . H9 H 0.9080 1.7089 0.8745 0.038 Uiso 1 1 calc R . . C10 C 0.9666(4) 1.5034(4) 0.8293(3) 0.0349(11) Uani 1 1 d . . . H10 H 1.0482 1.5435 0.8246 0.042 Uiso 1 1 calc R . . C11 C 0.9305(4) 1.3468(4) 0.8071(3) 0.0300(10) Uani 1 1 d . . . H11 H 0.9880 1.2783 0.7882 0.036 Uiso 1 1 calc R . . C12 C 0.8105(4) 1.2915(4) 0.8127(2) 0.0232(9) Uani 1 1 d . . . C13 C 0.7489(4) 1.1285(4) 0.7930(3) 0.0265(10) Uani 1 1 d . . . H13A H 0.7967 1.0507 0.8384 0.032 Uiso 1 1 calc R . . H13B H 0.7496 1.0908 0.7341 0.032 Uiso 1 1 calc R . . C14 C 0.3621(4) 0.9892(4) 0.9031(2) 0.0201(9) Uani 1 1 d . . . C15 C 0.3616(4) 0.8263(4) 0.9169(2) 0.0265(10) Uani 1 1 d . . . H15 H 0.4251 0.7581 0.9042 0.032 Uiso 1 1 calc R . . C16 C 0.2635(4) 0.7680(4) 0.9504(2) 0.0295(10) Uani 1 1 d . . . H16 H 0.2593 0.6569 0.9601 0.035 Uiso 1 1 calc R . . C17 C 0.1714(4) 0.8671(4) 0.9701(3) 0.0322(10) Uani 1 1 d . . . H17 H 0.1051 0.8241 0.9927 0.039 Uiso 1 1 calc R . . C18 C 0.1770(4) 1.0301(4) 0.9567(3) 0.0306(10) Uani 1 1 d . . . H18 H 0.1145 1.0991 0.9700 0.037 Uiso 1 1 calc R . . C19 C 0.2730(4) 1.0904(4) 0.9241(2) 0.0243(9) Uani 1 1 d . . . C20 C 0.3051(4) 1.2612(4) 0.9081(3) 0.0277(10) Uani 1 1 d . . . H20A H 0.3520 1.3155 0.9644 0.033 Uiso 1 1 calc R . . H20B H 0.2236 1.3214 0.8773 0.033 Uiso 1 1 calc R . . N2 N 0.6101(3) 1.3098(3) 0.83982(19) 0.0218(8) Uani 1 1 d . . . N5 N 0.4470(3) 1.0764(3) 0.8669(2) 0.0214(7) Uani 1 1 d . . . O1 O 0.5006(3) 1.4934(3) 0.89788(17) 0.0270(7) Uani 1 1 d . . . O2 O 0.5919(3) 0.8889(3) 0.84772(17) 0.0272(7) 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 0.031(3) 0.021(2) 0.017(2) 0.0030(15) 0.0042(19) 0.0027(17) C3 0.025(2) 0.0191(18) 0.024(2) -0.0031(15) 0.0071(19) 0.0013(16) C4 0.019(2) 0.022(2) 0.017(2) -0.0021(15) 0.0006(17) -0.0003(16) C6 0.020(2) 0.0194(19) 0.026(2) 0.0012(15) 0.0044(19) 0.0053(16) C7 0.020(2) 0.022(2) 0.022(2) 0.0011(15) 0.0067(18) -0.0005(16) C8 0.028(3) 0.022(2) 0.029(2) -0.0001(16) 0.0060(19) -0.0011(16) C9 0.032(3) 0.025(2) 0.036(3) 0.0002(18) 0.008(2) -0.0057(19) C10 0.029(3) 0.033(2) 0.042(3) 0.0031(19) 0.012(2) -0.0068(19) C11 0.024(3) 0.030(2) 0.035(3) 0.0011(17) 0.009(2) 0.0053(18) C12 0.020(2) 0.023(2) 0.025(2) 0.0017(15) 0.0043(18) -0.0005(16) C13 0.030(3) 0.021(2) 0.031(2) -0.0022(16) 0.013(2) 0.0037(17) C14 0.019(2) 0.0235(19) 0.017(2) -0.0009(15) 0.0055(18) -0.0031(17) C15 0.032(3) 0.026(2) 0.019(2) 0.0031(16) 0.0051(19) 0.0007(18) C16 0.038(3) 0.024(2) 0.024(2) -0.0015(16) 0.006(2) -0.0063(19) C17 0.031(3) 0.036(2) 0.030(3) 0.0003(18) 0.010(2) -0.007(2) C18 0.026(2) 0.037(2) 0.031(3) -0.0041(18) 0.012(2) 0.0021(19) C19 0.023(2) 0.024(2) 0.025(2) -0.0017(16) 0.0065(18) -0.0016(17) C20 0.021(2) 0.027(2) 0.036(3) -0.0005(17) 0.010(2) 0.0025(17) N2 0.028(2) 0.0160(16) 0.0227(18) -0.0047(12) 0.0089(16) -0.0029(13) N5 0.0221(19) 0.0161(16) 0.0272(19) 0.0004(12) 0.0092(15) 0.0011(13) O1 0.0334(17) 0.0197(14) 0.0289(16) -0.0009(11) 0.0109(13) 0.0036(12) O2 0.0288(17) 0.0204(14) 0.0333(16) -0.0033(11) 0.0106(13) 0.0004(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.227(4) . ? C1 N2 1.346(5) . ? C1 C6 1.516(5) . ? C3 N2 1.484(4) . ? C3 C4 1.513(5) . ? C3 C13 1.536(5) . ? C3 H3 1.0000 . ? C4 O2 1.225(4) . ? C4 N5 1.350(5) . ? C6 N5 1.491(4) . ? C6 C20 1.535(5) . ? C6 H6 1.0000 . ? C7 C8 1.387(5) . ? C7 C12 1.387(5) . ? C7 N2 1.419(5) . ? C8 C9 1.384(5) . ? C8 H8 0.9500 . ? C9 C10 1.401(6) . ? C9 H9 0.9500 . ? C10 C11 1.387(5) . ? C10 H10 0.9500 . ? C11 C12 1.378(5) . ? C11 H11 0.9500 . ? C12 C13 1.510(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.383(5) . ? C14 C15 1.389(5) . ? C14 N5 1.410(5) . ? C15 C16 1.391(6) . ? C15 H15 0.9500 . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.392(5) . ? C17 H17 0.9500 . ? C18 C19 1.369(5) . ? C18 H18 0.9500 . ? C19 C20 1.516(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 125.4(4) . . ? O1 C1 C6 121.8(4) . . ? N2 C1 C6 112.8(3) . . ? N2 C3 C4 111.5(3) . . ? N2 C3 C13 104.4(3) . . ? C4 C3 C13 116.3(3) . . ? N2 C3 H3 108.1 . . ? C4 C3 H3 108.1 . . ? C13 C3 H3 108.1 . . ? O2 C4 N5 124.9(3) . . ? O2 C4 C3 122.1(3) . . ? N5 C4 C3 112.9(3) . . ? N5 C6 C1 111.8(3) . . ? N5 C6 C20 104.1(3) . . ? C1 C6 C20 115.1(3) . . ? N5 C6 H6 108.5 . . ? C1 C6 H6 108.5 . . ? C20 C6 H6 108.5 . . ? C8 C7 C12 122.5(4) . . ? C8 C7 N2 128.1(3) . . ? C12 C7 N2 109.4(3) . . ? C9 C8 C7 116.7(4) . . ? C9 C8 H8 121.6 . . ? C7 C8 H8 121.6 . . ? C8 C9 C10 121.9(4) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 119.6(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 119.4(4) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 C13 129.8(4) . . ? C7 C12 C13 110.4(3) . . ? C12 C13 C3 103.5(3) . . ? C12 C13 H13A 111.1 . . ? C3 C13 H13A 111.1 . . ? C12 C13 H13B 111.1 . . ? C3 C13 H13B 111.1 . . ? H13A C13 H13B 109.0 . . ? C19 C14 C15 122.3(4) . . ? C19 C14 N5 110.0(3) . . ? C15 C14 N5 127.7(4) . . ? C14 C15 C16 116.6(4) . . ? C14 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? C17 C16 C15 122.0(4) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 119.5(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C14 120.0(3) . . ? C18 C19 C20 130.1(4) . . ? C14 C19 C20 109.9(3) . . ? C19 C20 C6 102.4(3) . . ? C19 C20 H20A 111.3 . . ? C6 C20 H20A 111.3 . . ? C19 C20 H20B 111.3 . . ? C6 C20 H20B 111.3 . . ? H20A C20 H20B 109.2 . . ? C1 N2 C7 128.2(3) . . ? C1 N2 C3 121.8(3) . . ? C7 N2 C3 109.8(3) . . ? C4 N5 C14 129.4(3) . . ? C4 N5 C6 121.4(3) . . ? C14 N5 C6 108.8(3) . . ? 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 N2 C3 C4 O2 -143.3(3) . . . . ? C13 C3 C4 O2 -23.8(5) . . . . ? N2 C3 C4 N5 39.2(4) . . . . ? C13 C3 C4 N5 158.7(3) . . . . ? O1 C1 C6 N5 -143.6(3) . . . . ? N2 C1 C6 N5 38.2(4) . . . . ? O1 C1 C6 C20 -25.1(5) . . . . ? N2 C1 C6 C20 156.7(3) . . . . ? C12 C7 C8 C9 0.8(5) . . . . ? N2 C7 C8 C9 -178.0(3) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? C9 C10 C11 C12 1.3(6) . . . . ? C10 C11 C12 C7 -0.8(6) . . . . ? C10 C11 C12 C13 -179.7(4) . . . . ? C8 C7 C12 C11 -0.3(6) . . . . ? N2 C7 C12 C11 178.7(3) . . . . ? C8 C7 C12 C13 178.9(3) . . . . ? N2 C7 C12 C13 -2.1(4) . . . . ? C11 C12 C13 C3 -169.7(4) . . . . ? C7 C12 C13 C3 11.3(4) . . . . ? N2 C3 C13 C12 -15.4(4) . . . . ? C4 C3 C13 C12 -138.7(3) . . . . ? C19 C14 C15 C16 2.1(5) . . . . ? N5 C14 C15 C16 -177.3(3) . . . . ? C14 C15 C16 C17 -0.7(6) . . . . ? C15 C16 C17 C18 -0.3(6) . . . . ? C16 C17 C18 C19 0.1(6) . . . . ? C17 C18 C19 C14 1.3(6) . . . . ? C17 C18 C19 C20 -176.4(4) . . . . ? C15 C14 C19 C18 -2.4(6) . . . . ? N5 C14 C19 C18 177.1(3) . . . . ? C15 C14 C19 C20 175.7(3) . . . . ? N5 C14 C19 C20 -4.8(4) . . . . ? C18 C19 C20 C6 -165.6(4) . . . . ? C14 C19 C20 C6 16.6(4) . . . . ? N5 C6 C20 C19 -21.1(4) . . . . ? C1 C6 C20 C19 -143.9(3) . . . . ? O1 C1 N2 C7 -1.1(6) . . . . ? C6 C1 N2 C7 177.0(3) . . . . ? O1 C1 N2 C3 -175.1(3) . . . . ? C6 C1 N2 C3 3.1(5) . . . . ? C8 C7 N2 C1 -4.1(6) . . . . ? C12 C7 N2 C1 176.9(3) . . . . ? C8 C7 N2 C3 170.4(3) . . . . ? C12 C7 N2 C3 -8.6(4) . . . . ? C4 C3 N2 C1 -43.5(4) . . . . ? C13 C3 N2 C1 -169.9(3) . . . . ? C4 C3 N2 C7 141.5(3) . . . . ? C13 C3 N2 C7 15.2(4) . . . . ? O2 C4 N5 C14 -4.0(6) . . . . ? C3 C4 N5 C14 173.5(3) . . . . ? O2 C4 N5 C6 -175.6(3) . . . . ? C3 C4 N5 C6 1.9(5) . . . . ? C19 C14 N5 C4 177.8(3) . . . . ? C15 C14 N5 C4 -2.7(6) . . . . ? C19 C14 N5 C6 -9.7(4) . . . . ? C15 C14 N5 C6 169.7(3) . . . . ? C1 C6 N5 C4 -42.3(4) . . . . ? C20 C6 N5 C4 -167.1(3) . . . . ? C1 C6 N5 C14 144.6(3) . . . . ? C20 C6 N5 C14 19.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.302 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.069 # Attachment '- Compound12.cif' data_xsodu194-3inv _database_code_depnum_ccdc_archive 'CCDC 783552' #TrackingRef '- Compound12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N2 O2' _chemical_formula_sum 'C7 H10 N2 O2' _chemical_formula_weight 154.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 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 5.8353(3) _cell_length_b 9.6510(6) _cell_length_c 12.8178(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 721.85(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4152 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7065 _exptl_absorpt_correction_T_max 0.9751 _exptl_absorpt_process_details 'SADABS 2008/2 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Kappa APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4138 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1777 _reflns_number_gt 1465 _reflns_threshold_expression >2\s(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS97 or SIR2002' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0393P)^2^+0.1355P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(18) _chemical_absolute_configuration syn _refine_ls_number_reflns 1777 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.2716(3) 0.1204(2) 0.81311(17) 0.0189(4) Uani 1 1 d . . . C3 C 0.5289(3) -0.0773(2) 0.83757(19) 0.0187(4) Uani 1 1 d . . . C4 C 0.3406(4) -0.1743(2) 0.80345(16) 0.0197(4) Uani 1 1 d . . . C6 C 0.1766(4) 0.0355(2) 0.72410(19) 0.0216(5) Uani 1 1 d . . . C7 C 0.5546(4) 0.1190(2) 0.95708(19) 0.0245(5) Uani 1 1 d . . . C8 C 0.7537(4) 0.0194(2) 0.9753(2) 0.0265(5) Uani 1 1 d . . . C9 C 0.6678(4) -0.1194(2) 0.93234(19) 0.0254(5) Uani 1 1 d . . . N2 N 0.4314(3) 0.05706(17) 0.86909(15) 0.0193(4) Uani 1 1 d . . . N5 N 0.1731(3) -0.11248(18) 0.74877(15) 0.0225(4) Uani 1 1 d . . . O1 O 0.2034(2) 0.24007(14) 0.83204(12) 0.0229(3) Uani 1 1 d . . . O2 O 0.3424(3) -0.29927(14) 0.82417(13) 0.0252(4) Uani 1 1 d . . . H3 H 0.627(4) -0.066(2) 0.779(2) 0.023(6) Uiso 1 1 d . . . H5 H 0.064(4) -0.162(3) 0.723(2) 0.025(7) Uiso 1 1 d . . . H6A H 0.019(4) 0.066(3) 0.7107(19) 0.022(6) Uiso 1 1 d . . . H6B H 0.273(4) 0.054(2) 0.6620(19) 0.024(6) Uiso 1 1 d . . . H7A H 0.454(5) 0.120(3) 1.018(2) 0.035(7) Uiso 1 1 d . . . H7B H 0.608(4) 0.217(3) 0.9388(19) 0.033(7) Uiso 1 1 d . . . H8A H 0.794(4) 0.017(2) 1.051(2) 0.027(7) Uiso 1 1 d . . . H8B H 0.892(4) 0.052(2) 0.9368(18) 0.015(6) Uiso 1 1 d . . . H9A H 0.562(5) -0.161(3) 0.984(2) 0.033(7) Uiso 1 1 d . . . H9B H 0.797(5) -0.178(2) 0.9164(19) 0.029(6) 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 0.0186(10) 0.0166(8) 0.0215(10) 0.0018(9) 0.0004(9) -0.0012(8) C3 0.0174(9) 0.0156(9) 0.0231(11) -0.0002(9) 0.0008(9) 0.0025(8) C4 0.0202(10) 0.0184(9) 0.0205(11) -0.0026(8) 0.0024(9) 0.0006(8) C6 0.0235(11) 0.0168(9) 0.0244(11) 0.0003(9) -0.0046(10) 0.0002(9) C7 0.0281(11) 0.0212(10) 0.0240(12) -0.0015(10) -0.0048(10) 0.0004(10) C8 0.0244(11) 0.0254(11) 0.0297(13) 0.0011(10) -0.0037(11) -0.0008(9) C9 0.0257(11) 0.0195(10) 0.0310(12) 0.0011(10) -0.0041(11) 0.0035(10) N2 0.0215(9) 0.0145(8) 0.0219(9) -0.0026(7) -0.0039(8) 0.0000(7) N5 0.0216(9) 0.0168(8) 0.0292(10) -0.0023(8) -0.0047(8) -0.0031(8) O1 0.0253(7) 0.0163(6) 0.0273(8) -0.0006(7) -0.0019(7) 0.0036(6) O2 0.0276(8) 0.0148(6) 0.0332(9) 0.0011(7) 0.0012(8) 0.0001(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.245(2) . ? C1 N2 1.326(3) . ? C1 C6 1.510(3) . ? C3 N2 1.472(3) . ? C3 C4 1.508(3) . ? C3 C9 1.516(3) . ? C3 H3 0.95(3) . ? C4 O2 1.235(2) . ? C4 N5 1.342(3) . ? C6 N5 1.463(3) . ? C6 H6A 0.98(2) . ? C6 H6B 0.99(3) . ? C7 N2 1.465(3) . ? C7 C8 1.526(3) . ? C7 H7A 0.97(3) . ? C7 H7B 1.02(3) . ? C8 C9 1.533(3) . ? C8 H8A 1.00(3) . ? C8 H8B 1.00(2) . ? C9 H9A 0.99(3) . ? C9 H9B 0.97(3) . ? N5 H5 0.86(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 O1 C1 N2 123.14(19) . . ? O1 C1 C6 122.22(18) . . ? N2 C1 C6 114.64(18) . . ? N2 C3 C4 110.17(16) . . ? N2 C3 C9 102.89(17) . . ? C4 C3 C9 117.07(19) . . ? N2 C3 H3 110.4(14) . . ? C4 C3 H3 106.5(15) . . ? C9 C3 H3 109.8(15) . . ? O2 C4 N5 123.5(2) . . ? O2 C4 C3 122.5(2) . . ? N5 C4 C3 113.95(17) . . ? N5 C6 C1 111.80(18) . . ? N5 C6 H6A 108.6(15) . . ? C1 C6 H6A 108.3(14) . . ? N5 C6 H6B 110.9(13) . . ? C1 C6 H6B 107.5(14) . . ? H6A C6 H6B 110(2) . . ? N2 C7 C8 103.53(18) . . ? N2 C7 H7A 108.8(16) . . ? C8 C7 H7A 110.3(16) . . ? N2 C7 H7B 110.5(14) . . ? C8 C7 H7B 112.6(15) . . ? H7A C7 H7B 111(2) . . ? C7 C8 C9 104.29(19) . . ? C7 C8 H8A 109.9(14) . . ? C9 C8 H8A 114.0(13) . . ? C7 C8 H8B 109.8(13) . . ? C9 C8 H8B 111.5(13) . . ? H8A C8 H8B 107(2) . . ? C3 C9 C8 103.16(18) . . ? C3 C9 H9A 108.1(16) . . ? C8 C9 H9A 108.8(15) . . ? C3 C9 H9B 114.0(15) . . ? C8 C9 H9B 109.5(15) . . ? H9A C9 H9B 113(2) . . ? C1 N2 C7 124.98(18) . . ? C1 N2 C3 121.95(17) . . ? C7 N2 C3 112.41(17) . . ? C4 N5 C6 122.45(18) . . ? C4 N5 H5 119.5(16) . . ? C6 N5 H5 117.9(16) . . ? 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 N2 C3 C4 O2 -141.4(2) . . . . ? C9 C3 C4 O2 -24.4(3) . . . . ? N2 C3 C4 N5 38.7(2) . . . . ? C9 C3 C4 N5 155.78(19) . . . . ? O1 C1 C6 N5 -147.3(2) . . . . ? N2 C1 C6 N5 32.4(3) . . . . ? N2 C7 C8 C9 -25.3(2) . . . . ? N2 C3 C9 C8 -33.4(2) . . . . ? C4 C3 C9 C8 -154.31(19) . . . . ? C7 C8 C9 C3 36.9(2) . . . . ? O1 C1 N2 C7 -2.3(3) . . . . ? C6 C1 N2 C7 177.9(2) . . . . ? O1 C1 N2 C3 -172.36(19) . . . . ? C6 C1 N2 C3 7.9(3) . . . . ? C8 C7 N2 C1 -166.48(19) . . . . ? C8 C7 N2 C3 4.4(2) . . . . ? C4 C3 N2 C1 -44.8(3) . . . . ? C9 C3 N2 C1 -170.32(19) . . . . ? C4 C3 N2 C7 144.06(19) . . . . ? C9 C3 N2 C7 18.5(2) . . . . ? O2 C4 N5 C6 -179.2(2) . . . . ? C3 C4 N5 C6 0.6(3) . . . . ? C1 C6 N5 C4 -37.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.198 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.052 # Attachment '- Compound13.cif' data_xsodu204-2 _database_code_depnum_ccdc_archive 'CCDC 783553' #TrackingRef '- Compound13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 N2 O2' _chemical_formula_sum 'C12 H18 N2 O2' _chemical_formula_weight 222.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 6.0475(7) _cell_length_b 7.8473(10) _cell_length_c 11.2904(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.541(7) _cell_angle_gamma 90.00 _cell_volume 531.17(11) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3519 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5474 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS (Sheldrick, G. M., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Kappa APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2989 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0766 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 28.53 _reflns_number_total 1334 _reflns_number_gt 904 _reflns_threshold_expression >2\s(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS97 or SIR2002' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0452P)^2^+0.3347P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1334 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.0956(3) 0.3519(3) 0.44771(19) 0.0210(5) Uani 1 1 d . . . C2 C -0.0315(3) 0.3336(3) 0.55466(19) 0.0203(5) Uani 1 1 d . . . H2 H 0.0712 0.2785 0.6202 0.024 Uiso 1 1 calc R . . C3 C -0.2303(4) 0.2132(3) 0.5225(2) 0.0234(5) Uani 1 1 d . . . H3A H -0.3310 0.2613 0.4545 0.028 Uiso 1 1 calc R . . H3B H -0.1757 0.1017 0.4973 0.028 Uiso 1 1 calc R . . C4 C -0.3598(4) 0.1873(3) 0.6285(2) 0.0263(5) Uani 1 1 d . . . H4A H -0.4945 0.1180 0.6032 0.032 Uiso 1 1 calc R . . H4B H -0.2657 0.1248 0.6926 0.032 Uiso 1 1 calc R . . C5 C -0.4286(4) 0.3584(3) 0.6765(2) 0.0245(5) Uani 1 1 d . . . H5A H -0.5370 0.4149 0.6157 0.029 Uiso 1 1 calc R . . H5B H -0.5020 0.3396 0.7488 0.029 Uiso 1 1 calc R . . C6 C -0.2262(4) 0.4723(3) 0.70715(19) 0.0238(5) Uani 1 1 d . . . H6A H -0.2741 0.5849 0.7340 0.029 Uiso 1 1 calc R . . H6B H -0.1241 0.4208 0.7732 0.029 Uiso 1 1 calc R . . N2 N 0.1086(3) 0.5061(2) 0.39831(15) 0.0217(4) Uani 1 1 d . . . O1 O 0.1764(3) 0.22244(19) 0.40954(14) 0.0278(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 0.0180(10) 0.0213(11) 0.0237(11) -0.0014(9) 0.0025(8) -0.0010(8) C2 0.0178(10) 0.0185(11) 0.0247(11) 0.0013(9) 0.0031(8) 0.0003(8) C3 0.0249(11) 0.0202(11) 0.0263(11) -0.0026(9) 0.0076(9) -0.0038(9) C4 0.0273(11) 0.0223(11) 0.0310(12) 0.0000(10) 0.0102(10) -0.0054(9) C5 0.0240(11) 0.0263(12) 0.0244(11) 0.0009(10) 0.0084(9) -0.0008(9) C6 0.0280(11) 0.0242(11) 0.0207(11) -0.0005(9) 0.0082(9) -0.0030(9) N2 0.0230(9) 0.0207(9) 0.0228(9) -0.0015(7) 0.0082(8) -0.0017(7) O1 0.0292(8) 0.0201(8) 0.0360(9) -0.0034(7) 0.0120(7) 0.0010(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.230(2) . ? C1 N2 1.339(3) . ? C1 C2 1.521(3) . ? C2 N2 1.465(3) 3_566 ? C2 C3 1.535(3) . ? C2 H2 1.0000 . ? C3 C4 1.528(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.518(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N2 1.475(2) 3_566 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N2 C2 1.465(3) 3_566 ? N2 C6 1.475(2) 3_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N2 123.58(18) . . ? O1 C1 C2 117.75(18) . . ? N2 C1 C2 118.65(17) . . ? N2 C2 C1 115.14(16) 3_566 . ? N2 C2 C3 109.74(16) 3_566 . ? C1 C2 C3 109.38(17) . . ? N2 C2 H2 107.4 3_566 . ? C1 C2 H2 107.4 . . ? C3 C2 H2 107.4 . . ? C4 C3 C2 111.26(18) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 110.67(17) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 110.48(17) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? N2 C6 C5 110.09(17) 3_566 . ? N2 C6 H6A 109.6 3_566 . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 3_566 . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? C1 N2 C2 125.87(16) . 3_566 ? C1 N2 C6 120.08(17) . 3_566 ? C2 N2 C6 113.83(16) 3_566 3_566 ? 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 O1 C1 C2 N2 175.44(19) . . . 3_566 ? N2 C1 C2 N2 -6.4(3) . . . 3_566 ? O1 C1 C2 C3 -60.5(2) . . . . ? N2 C1 C2 C3 117.7(2) . . . . ? N2 C2 C3 C4 -54.2(2) 3_566 . . . ? C1 C2 C3 C4 178.56(18) . . . . ? C2 C3 C4 C5 54.0(2) . . . . ? C3 C4 C5 C6 -54.9(2) . . . . ? C4 C5 C6 N2 56.3(2) . . . 3_566 ? O1 C1 N2 C2 -174.8(2) . . . 3_566 ? C2 C1 N2 C2 7.1(3) . . . 3_566 ? O1 C1 N2 C6 -0.5(3) . . . 3_566 ? C2 C1 N2 C6 -178.64(18) . . . 3_566 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.334 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.061 # Attachment '- Compound 1.cif' data_sodu142 _database_code_depnum_ccdc_archive 'CCDC 809091' #TrackingRef '- Compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N2 O2' _chemical_formula_sum 'C4 H6 N2 O2' _chemical_formula_weight 114.11 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 3.9045(4) _cell_length_b 11.5645(17) _cell_length_c 5.1679(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.461(8) _cell_angle_gamma 90.00 _cell_volume 231.87(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 499 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 120 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7456 _exptl_absorpt_correction_T_max 0.8621 _exptl_absorpt_process_details 'SADABS (Sheldrick, G. M., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Kappa APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1467 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 28.50 _reflns_number_total 570 _reflns_number_gt 509 _reflns_threshold_expression >2\s(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS97 or SIR2002' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0293P)^2^+0.1221P] 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 570 _refine_ls_number_parameters 41 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H3 H 0.690(4) -0.0724(16) 0.138(3) 0.024(4) Uiso 1 1 d . . . O1 O 0.5940(2) 0.13328(8) 0.16807(18) 0.0198(3) Uani 1 1 d . . . C4 C 0.9828(3) 0.12390(10) 0.5531(2) 0.0160(3) Uani 1 1 d . . . H4A H 1.1377 0.1836 0.4932 0.019 Uiso 1 1 calc R . . H4B H 0.8193 0.1634 0.6569 0.019 Uiso 1 1 calc R . . C2 C 0.7819(3) 0.06977(11) 0.3185(2) 0.0155(3) Uani 1 1 d . . . N3 N 0.8114(3) -0.04301(9) 0.2787(2) 0.0169(3) 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 O1 0.0240(5) 0.0161(5) 0.0180(5) 0.0015(3) -0.0041(4) 0.0010(3) C4 0.0179(6) 0.0131(6) 0.0161(6) -0.0008(5) -0.0016(4) 0.0006(4) C2 0.0158(6) 0.0172(6) 0.0135(6) 0.0003(5) 0.0017(4) -0.0012(5) N3 0.0209(6) 0.0152(6) 0.0134(5) -0.0016(4) -0.0030(4) -0.0008(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.2465(15) . ? C4 N3 1.4556(15) 3_756 ? C4 C2 1.5044(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C2 N3 1.3273(17) . ? N3 C4 1.4556(15) 3_756 ? N3 H3 0.889(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 N3 C4 C2 114.61(10) 3_756 . ? N3 C4 H4A 108.6 3_756 . ? C2 C4 H4A 108.6 . . ? N3 C4 H4B 108.6 3_756 . ? C2 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? O1 C2 N3 122.53(12) . . ? O1 C2 C4 118.31(11) . . ? N3 C2 C4 119.16(11) . . ? C2 N3 C4 126.21(10) . 3_756 ? C2 N3 H3 117.0(11) . . ? C4 N3 H3 116.8(11) 3_756 . ? 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 N3 C4 C2 O1 178.56(11) 3_756 . . . ? N3 C4 C2 N3 -1.62(18) 3_756 . . . ? O1 C2 N3 C4 -178.36(12) . . . 3_756 ? C4 C2 N3 C4 1.8(2) . . . 3_756 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.284 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.049