# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_a _database_code_depnum_ccdc_archive 'CCDC 919541' #TrackingRef 'web_deposit_cif_file_0_guangli_1358151266.9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N O3' _chemical_formula_sum 'C10 H15 N O3' _chemical_formula_weight 197.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 7.6770(15) _cell_length_b 14.890(3) _cell_length_c 8.9195(18) _cell_angle_alpha 90.00 _cell_angle_beta 105.14(3) _cell_angle_gamma 90.00 _cell_volume 984.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3572 _cell_measurement_theta_min 1.3676 _cell_measurement_theta_max 27.4814 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7155 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6514 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2255 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-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^ > 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^)+(0.0387P)^2^+0.6270P] 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 2255 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 0.97912(17) 0.88512(9) 0.24770(14) 0.0225(3) Uani 1 1 d . . . O2 O 0.87642(19) 0.86315(9) 0.52558(15) 0.0275(3) Uani 1 1 d . . . O3 O 0.51030(19) 1.06973(9) 0.17663(16) 0.0309(4) Uani 1 1 d . . . N1 N 0.6853(2) 0.94848(10) 0.14829(18) 0.0235(4) Uani 1 1 d . . . H1 H 0.6662 0.9505 0.0467 0.028 Uiso 1 1 calc R . . C1 C 1.2175(3) 0.87174(16) 0.1280(3) 0.0353(5) Uani 1 1 d . . . H1A H 1.2830 0.8335 0.2137 0.053 Uiso 1 1 calc R . . H1C H 1.2484 0.9348 0.1533 0.053 Uiso 1 1 calc R . . H1B H 1.2511 0.8554 0.0329 0.053 Uiso 1 1 calc R . . C2 C 1.0170(3) 0.85870(13) 0.1037(2) 0.0243(4) Uani 1 1 d . . . H2 H 0.9509 0.8996 0.0189 0.029 Uiso 1 1 calc R . . C3 C 0.9542(3) 0.76284(13) 0.0635(2) 0.0261(4) Uani 1 1 d . . . H3B H 1.0247 0.7215 0.1436 0.031 Uiso 1 1 calc R . . H3A H 0.9759 0.7461 -0.0375 0.031 Uiso 1 1 calc R . . C4 C 0.7546(3) 0.75327(13) 0.0543(2) 0.0271(4) Uani 1 1 d . . . H4A H 0.7177 0.6897 0.0358 0.033 Uiso 1 1 calc R . . H4B H 0.6825 0.7895 -0.0331 0.033 Uiso 1 1 calc R . . C5 C 0.7206(3) 0.78534(13) 0.2064(2) 0.0254(4) Uani 1 1 d . . . H5B H 0.7796 0.7438 0.2910 0.030 Uiso 1 1 calc R . . H5A H 0.5893 0.7846 0.1974 0.030 Uiso 1 1 calc R . . C6 C 0.7934(2) 0.87999(12) 0.2465(2) 0.0213(4) Uani 1 1 d . . . C7 C 0.7855(2) 0.91223(12) 0.4061(2) 0.0221(4) Uani 1 1 d . . . C8 C 0.8778(3) 0.89846(14) 0.6761(2) 0.0301(5) Uani 1 1 d . . . H8B H 0.9525 0.8600 0.7569 0.045 Uiso 1 1 calc R . . H8A H 0.7543 0.8999 0.6875 0.045 Uiso 1 1 calc R . . H8C H 0.9275 0.9594 0.6863 0.045 Uiso 1 1 calc R . . C9 C 0.6884(3) 0.98750(13) 0.3977(2) 0.0244(4) Uani 1 1 d . . . H9 H 0.6691 1.0208 0.4828 0.029 Uiso 1 1 calc R . . C10 C 0.6172(3) 1.00913(12) 0.2325(2) 0.0238(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 O1 0.0200(7) 0.0288(7) 0.0204(6) -0.0026(5) 0.0080(5) -0.0002(5) O2 0.0348(8) 0.0292(7) 0.0203(7) 0.0027(5) 0.0104(6) 0.0084(6) O3 0.0329(8) 0.0282(7) 0.0297(8) -0.0002(6) 0.0051(6) 0.0107(6) N1 0.0265(8) 0.0256(8) 0.0190(7) 0.0015(6) 0.0073(6) 0.0063(6) C1 0.0287(11) 0.0438(13) 0.0387(12) -0.0055(10) 0.0181(9) -0.0021(9) C2 0.0251(10) 0.0295(10) 0.0208(9) 0.0002(7) 0.0105(7) 0.0007(8) C3 0.0278(10) 0.0293(10) 0.0240(9) -0.0017(8) 0.0119(7) 0.0044(8) C4 0.0273(10) 0.0242(9) 0.0296(10) -0.0050(8) 0.0069(8) 0.0001(8) C5 0.0227(10) 0.0248(9) 0.0303(10) -0.0008(8) 0.0098(7) 0.0007(7) C6 0.0179(9) 0.0246(9) 0.0226(9) 0.0021(7) 0.0076(7) 0.0028(7) C7 0.0222(9) 0.0251(9) 0.0206(9) 0.0005(7) 0.0088(7) -0.0003(7) C8 0.0385(12) 0.0314(10) 0.0221(9) 0.0003(8) 0.0109(8) 0.0040(9) C9 0.0260(10) 0.0255(9) 0.0240(9) -0.0019(7) 0.0104(7) 0.0016(7) C10 0.0236(9) 0.0208(9) 0.0277(10) -0.0018(7) 0.0082(7) 0.0001(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 O1 C6 1.425(2) . ? O1 C2 1.443(2) . ? O2 C7 1.330(2) . ? O2 C8 1.439(2) . ? O3 C10 1.234(2) . ? N1 C10 1.363(2) . ? N1 C6 1.455(2) . ? N1 H1 0.8800 . ? C1 C2 1.510(3) . ? C1 H1A 0.9800 . ? C1 H1C 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.519(3) . ? C2 H2 1.0000 . ? C3 C4 1.520(3) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C5 1.524(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.524(3) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 C7 1.518(2) . ? C7 C9 1.337(3) . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.467(3) . ? C9 H9 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C2 114.35(14) . . ? C7 O2 C8 114.91(15) . . ? C10 N1 C6 111.91(15) . . ? C10 N1 H1 124.0 . . ? C6 N1 H1 124.0 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? O1 C2 C1 105.78(15) . . ? O1 C2 C3 109.95(15) . . ? C1 C2 C3 113.78(17) . . ? O1 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C2 C3 C4 110.72(16) . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? H3B C3 H3A 108.1 . . ? C3 C4 C5 109.13(16) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C4 C5 C6 111.18(16) . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? H5B C5 H5A 108.0 . . ? O1 C6 N1 112.28(15) . . ? O1 C6 C7 105.13(14) . . ? N1 C6 C7 100.75(14) . . ? O1 C6 C5 110.87(14) . . ? N1 C6 C5 112.97(15) . . ? C7 C6 C5 114.24(15) . . ? O2 C7 C9 132.34(18) . . ? O2 C7 C6 115.87(15) . . ? C9 C7 C6 111.77(16) . . ? O2 C8 H8B 109.5 . . ? O2 C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? O2 C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? C7 C9 C10 107.22(17) . . ? C7 C9 H9 126.4 . . ? C10 C9 H9 126.4 . . ? O3 C10 N1 124.90(17) . . ? O3 C10 C9 126.89(18) . . ? N1 C10 C9 108.18(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 C6 O1 C2 C1 178.27(15) . . . . ? C6 O1 C2 C3 -58.48(19) . . . . ? O1 C2 C3 C4 56.8(2) . . . . ? C1 C2 C3 C4 175.21(16) . . . . ? C2 C3 C4 C5 -55.3(2) . . . . ? C3 C4 C5 C6 53.8(2) . . . . ? C2 O1 C6 N1 -70.23(19) . . . . ? C2 O1 C6 C7 -178.87(14) . . . . ? C2 O1 C6 C5 57.19(19) . . . . ? C10 N1 C6 O1 -113.76(17) . . . . ? C10 N1 C6 C7 -2.35(19) . . . . ? C10 N1 C6 C5 119.95(18) . . . . ? C4 C5 C6 O1 -54.2(2) . . . . ? C4 C5 C6 N1 72.8(2) . . . . ? C4 C5 C6 C7 -172.80(15) . . . . ? C8 O2 C7 C9 -2.7(3) . . . . ? C8 O2 C7 C6 175.73(16) . . . . ? O1 C6 C7 O2 -62.19(19) . . . . ? N1 C6 C7 O2 -179.01(15) . . . . ? C5 C6 C7 O2 59.6(2) . . . . ? O1 C6 C7 C9 116.54(17) . . . . ? N1 C6 C7 C9 -0.3(2) . . . . ? C5 C6 C7 C9 -121.69(18) . . . . ? O2 C7 C9 C10 -178.99(19) . . . . ? C6 C7 C9 C10 2.6(2) . . . . ? C6 N1 C10 O3 -174.22(18) . . . . ? C6 N1 C10 C9 4.0(2) . . . . ? C7 C9 C10 O3 174.14(19) . . . . ? C7 C9 C10 N1 -4.0(2) . . . . ? 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 N1 H1 O3 0.88 2.12 2.908(2) 149.0 3_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.359 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.053 data_a2 _database_code_depnum_ccdc_archive 'CCDC 919542' #TrackingRef 'web_deposit_cif_file_1_guangli_1358151266.4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H17 N O3' _chemical_formula_sum 'C10 H17 N O3' _chemical_formula_weight 199.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.826(3) _cell_length_b 9.5792(19) _cell_length_c 16.063(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2127.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6096 _cell_measurement_theta_min 1.2677 _cell_measurement_theta_max 27.4764 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6676 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12526 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2428 _reflns_number_gt 2166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+1.0603P] 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 2428 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _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 -0.21142(9) 0.81859(14) 0.59507(8) 0.0353(3) Uani 1 1 d . . . O2 O -0.04884(10) 0.61535(13) 0.41611(7) 0.0315(3) Uani 1 1 d . . . O3 O 0.04279(8) 0.84847(12) 0.61967(7) 0.0262(3) Uani 1 1 d . . . N1 N -0.03317(11) 0.65360(14) 0.55626(8) 0.0250(3) Uani 1 1 d . . . H1 H -0.0127 0.5697 0.5699 0.030 Uiso 1 1 calc R . . C1 C -0.05759(12) 0.68967(18) 0.47830(10) 0.0247(4) Uani 1 1 d . . . C2 C -0.09792(13) 0.83578(17) 0.47980(11) 0.0262(4) Uani 1 1 d . . . H2A H -0.1583 0.8419 0.4469 0.031 Uiso 1 1 calc R . . H2B H -0.0505 0.9036 0.4574 0.031 Uiso 1 1 calc R . . C3 C -0.11739(12) 0.86259(18) 0.57207(11) 0.0254(4) Uani 1 1 d . . . H3 H -0.1065 0.9628 0.5867 0.030 Uiso 1 1 calc R . . C4 C -0.28364(15) 0.9168(3) 0.57188(14) 0.0457(6) Uani 1 1 d . . . H4A H -0.2685 1.0078 0.5965 0.069 Uiso 1 1 calc R . . H4B H -0.3468 0.8849 0.5921 0.069 Uiso 1 1 calc R . . H4C H -0.2854 0.9252 0.5111 0.069 Uiso 1 1 calc R . . C5 C -0.04395(12) 0.76709(17) 0.61603(10) 0.0231(4) Uani 1 1 d . . . C6 C -0.07238(13) 0.7162(2) 0.70194(11) 0.0300(4) Uani 1 1 d . . . H6A H -0.1289 0.6532 0.6973 0.036 Uiso 1 1 calc R . . H6B H -0.0915 0.7970 0.7367 0.036 Uiso 1 1 calc R . . C7 C 0.01067(15) 0.6389(2) 0.74399(12) 0.0356(5) Uani 1 1 d . . . H7B H -0.0072 0.6156 0.8020 0.043 Uiso 1 1 calc R . . H7A H 0.0239 0.5506 0.7140 0.043 Uiso 1 1 calc R . . C8 C 0.10043(15) 0.7300(2) 0.74356(12) 0.0377(5) Uani 1 1 d . . . H8A H 0.0896 0.8127 0.7793 0.045 Uiso 1 1 calc R . . H8B H 0.1557 0.6769 0.7667 0.045 Uiso 1 1 calc R . . C9 C 0.12437(13) 0.77713(19) 0.65608(11) 0.0303(4) Uani 1 1 d . . . H9 H 0.1400 0.6933 0.6215 0.036 Uiso 1 1 calc R . . C10 C 0.20805(15) 0.8782(2) 0.65167(15) 0.0474(6) Uani 1 1 d . . . H10A H 0.2658 0.8348 0.6758 0.071 Uiso 1 1 calc R . . H10C H 0.1920 0.9629 0.6829 0.071 Uiso 1 1 calc R . . H10B H 0.2207 0.9024 0.5934 0.071 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 0.0238(6) 0.0408(8) 0.0413(8) 0.0091(6) 0.0044(6) 0.0033(6) O2 0.0401(8) 0.0287(7) 0.0257(6) -0.0035(5) -0.0030(6) 0.0084(6) O3 0.0246(6) 0.0229(6) 0.0312(6) 0.0002(5) -0.0024(5) 0.0002(5) N1 0.0339(8) 0.0168(7) 0.0243(7) -0.0004(5) -0.0011(6) 0.0036(6) C1 0.0256(9) 0.0232(9) 0.0254(8) 0.0005(6) 0.0010(7) 0.0007(7) C2 0.0302(9) 0.0210(8) 0.0275(9) 0.0020(7) 0.0000(7) 0.0025(7) C3 0.0244(8) 0.0216(8) 0.0301(9) 0.0002(7) 0.0030(7) 0.0010(7) C4 0.0300(10) 0.0600(15) 0.0473(12) 0.0119(11) 0.0055(10) 0.0156(10) C5 0.0248(8) 0.0189(8) 0.0255(8) -0.0023(6) 0.0020(7) 0.0007(6) C6 0.0345(10) 0.0293(10) 0.0261(9) -0.0010(7) 0.0047(8) -0.0008(8) C7 0.0484(12) 0.0341(10) 0.0242(9) 0.0044(8) 0.0012(9) 0.0047(9) C8 0.0423(12) 0.0409(11) 0.0300(9) -0.0002(8) -0.0077(9) 0.0071(9) C9 0.0273(9) 0.0294(10) 0.0341(10) 0.0010(7) -0.0028(8) 0.0059(7) C10 0.0317(11) 0.0507(13) 0.0597(14) 0.0090(11) -0.0089(11) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.416(2) . ? O1 C4 1.421(2) . ? O2 C1 1.233(2) . ? O3 C5 1.432(2) . ? O3 C9 1.443(2) . ? N1 C1 1.342(2) . ? N1 C5 1.458(2) . ? N1 H1 0.8800 . ? C1 C2 1.507(2) . ? C2 C3 1.528(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.538(2) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.515(2) . ? C6 C7 1.525(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.517(3) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C8 C9 1.513(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.510(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? 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 C3 O1 C4 112.32(15) . . ? C5 O3 C9 114.43(13) . . ? C1 N1 C5 113.37(14) . . ? C1 N1 H1 123.3 . . ? C5 N1 H1 123.3 . . ? O2 C1 N1 125.64(16) . . ? O2 C1 C2 125.86(16) . . ? N1 C1 C2 108.50(14) . . ? C1 C2 C3 103.70(14) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? O1 C3 C2 111.40(14) . . ? O1 C3 C5 108.01(13) . . ? C2 C3 C5 103.24(13) . . ? O1 C3 H3 111.3 . . ? C2 C3 H3 111.3 . . ? C5 C3 H3 111.3 . . ? O1 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 C5 N1 110.32(13) . . ? O3 C5 C6 110.80(14) . . ? N1 C5 C6 112.74(14) . . ? O3 C5 C3 104.35(13) . . ? N1 C5 C3 102.04(13) . . ? C6 C5 C3 115.98(14) . . ? C5 C6 C7 111.37(15) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 109.53(15) . . ? C8 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? C8 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? H7B C7 H7A 108.2 . . ? C9 C8 C7 110.80(16) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O3 C9 C10 106.04(15) . . ? O3 C9 C8 110.29(15) . . ? C10 C9 C8 113.75(17) . . ? O3 C9 H9 108.9 . . ? C10 C9 H9 108.9 . . ? C8 C9 H9 108.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? H10C C10 H10B 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 C5 N1 C1 O2 175.02(17) . . . . ? C5 N1 C1 C2 -5.3(2) . . . . ? O2 C1 C2 C3 165.30(17) . . . . ? N1 C1 C2 C3 -14.38(19) . . . . ? C4 O1 C3 C2 -79.45(19) . . . . ? C4 O1 C3 C5 167.84(15) . . . . ? C1 C2 C3 O1 -88.80(16) . . . . ? C1 C2 C3 C5 26.89(17) . . . . ? C9 O3 C5 N1 -68.72(17) . . . . ? C9 O3 C5 C6 56.84(18) . . . . ? C9 O3 C5 C3 -177.65(13) . . . . ? C1 N1 C5 O3 -88.06(17) . . . . ? C1 N1 C5 C6 147.48(15) . . . . ? C1 N1 C5 C3 22.38(18) . . . . ? O1 C3 C5 O3 -156.38(13) . . . . ? C2 C3 C5 O3 85.54(15) . . . . ? O1 C3 C5 N1 88.72(15) . . . . ? C2 C3 C5 N1 -29.36(16) . . . . ? O1 C3 C5 C6 -34.2(2) . . . . ? C2 C3 C5 C6 -152.28(15) . . . . ? O3 C5 C6 C7 -53.83(19) . . . . ? N1 C5 C6 C7 70.37(19) . . . . ? C3 C5 C6 C7 -172.52(15) . . . . ? C5 C6 C7 C8 53.4(2) . . . . ? C6 C7 C8 C9 -54.6(2) . . . . ? C5 O3 C9 C10 178.34(15) . . . . ? C5 O3 C9 C8 -58.08(19) . . . . ? C7 C8 C9 O3 56.2(2) . . . . ? C7 C8 C9 C10 175.14(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 N1 H1 O2 0.88 1.98 2.8495(19) 170.0 5_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.041 data_a3 _database_code_depnum_ccdc_archive 'CCDC 919543' #TrackingRef 'web_deposit_cif_file_2_guangli_1358151266.4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H17 N O3' _chemical_formula_sum 'C10 H17 N O3' _chemical_formula_weight 199.25 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 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 25.951(5) _cell_length_b 5.6442(11) _cell_length_c 15.203(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.62(3) _cell_angle_gamma 90.00 _cell_volume 2040.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3477 _cell_measurement_theta_min 1.7130 _cell_measurement_theta_max 27.4824 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6611 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7381 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2343 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0435P)^2^+3.6638P] 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 2343 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0833 _refine_ls_wR_factor_ref 0.1678 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _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 0.24179(7) 1.2839(3) 0.11196(13) 0.0300(4) Uani 1 1 d . . . O2 O 0.39216(7) 0.8093(3) 0.30983(13) 0.0316(5) Uani 1 1 d . . . O3 O 0.40094(7) 0.9858(3) 0.15305(12) 0.0241(4) Uani 1 1 d . . . N1 N 0.30151(8) 1.0312(4) 0.08143(14) 0.0235(5) Uani 1 1 d . . . H1 H 0.2887 1.0593 0.0194 0.028 Uiso 1 1 calc R . . C1 C 0.27933(10) 1.1335(4) 0.13820(18) 0.0236(5) Uani 1 1 d . . . C2 C 0.30797(11) 1.0342(5) 0.23748(18) 0.0280(6) Uani 1 1 d . . . H2A H 0.2800 0.9823 0.2626 0.034 Uiso 1 1 calc R . . H2B H 0.3330 1.1539 0.2817 0.034 Uiso 1 1 calc R . . C3 C 0.34182(10) 0.8242(5) 0.22673(17) 0.0248(5) Uani 1 1 d . . . H3 H 0.3196 0.6757 0.2205 0.030 Uiso 1 1 calc R . . C4 C 0.42513(12) 0.6044(5) 0.3141(2) 0.0374(7) Uani 1 1 d . . . H4B H 0.4433 0.6222 0.2690 0.056 Uiso 1 1 calc R . . H4A H 0.4008 0.4642 0.2968 0.056 Uiso 1 1 calc R . . H4C H 0.4540 0.5859 0.3794 0.056 Uiso 1 1 calc R . . C5 C 0.34832(9) 0.8705(4) 0.13019(17) 0.0210(5) Uani 1 1 d . . . C6 C 0.34378(10) 0.6479(4) 0.07075(18) 0.0247(5) Uani 1 1 d . . . H6A H 0.3057 0.5788 0.0516 0.030 Uiso 1 1 calc R . . H6B H 0.3715 0.5294 0.1105 0.030 Uiso 1 1 calc R . . C7 C 0.35445(11) 0.7007(5) -0.01895(18) 0.0276(6) Uani 1 1 d . . . H7A H 0.3239 0.8014 -0.0634 0.033 Uiso 1 1 calc R . . H7B H 0.3551 0.5510 -0.0524 0.033 Uiso 1 1 calc R . . C8 C 0.41086(11) 0.8284(5) 0.0104(2) 0.0307(6) Uani 1 1 d . . . H8A H 0.4417 0.7197 0.0482 0.037 Uiso 1 1 calc R . . H8B H 0.4165 0.8760 -0.0478 0.037 Uiso 1 1 calc R . . C9 C 0.41242(10) 1.0459(5) 0.06977(18) 0.0271(6) Uani 1 1 d . . . H9 H 0.3833 1.1607 0.0290 0.032 Uiso 1 1 calc R . . C10 C 0.46914(11) 1.1685(5) 0.1093(2) 0.0365(7) Uani 1 1 d . . . H10B H 0.4677 1.3055 0.1478 0.055 Uiso 1 1 calc R . . H10C H 0.4784 1.2218 0.0560 0.055 Uiso 1 1 calc R . . H10A H 0.4980 1.0576 0.1496 0.055 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 0.0287(9) 0.0338(10) 0.0304(10) 0.0042(8) 0.0148(8) 0.0109(8) O2 0.0257(9) 0.0405(11) 0.0248(9) 0.0039(8) 0.0060(8) 0.0046(8) O3 0.0195(8) 0.0257(9) 0.0279(9) -0.0006(7) 0.0103(7) -0.0023(7) N1 0.0215(10) 0.0268(11) 0.0226(10) 0.0024(9) 0.0091(8) 0.0034(9) C1 0.0200(11) 0.0255(12) 0.0273(12) -0.0019(10) 0.0116(10) -0.0028(10) C2 0.0285(13) 0.0327(14) 0.0267(13) 0.0007(11) 0.0151(11) 0.0013(12) C3 0.0220(11) 0.0282(13) 0.0242(12) 0.0033(10) 0.0092(10) -0.0016(11) C4 0.0303(14) 0.0402(16) 0.0371(15) 0.0108(13) 0.0088(12) 0.0107(13) C5 0.0165(10) 0.0237(11) 0.0229(11) 0.0005(10) 0.0080(9) -0.0017(9) C6 0.0217(11) 0.0245(12) 0.0267(12) -0.0004(10) 0.0085(10) -0.0012(10) C7 0.0298(13) 0.0257(12) 0.0260(13) -0.0038(10) 0.0098(11) 0.0033(11) C8 0.0292(13) 0.0311(14) 0.0362(14) 0.0018(12) 0.0176(12) 0.0044(12) C9 0.0248(12) 0.0288(13) 0.0308(13) 0.0052(11) 0.0144(11) 0.0013(11) C10 0.0284(13) 0.0387(16) 0.0472(17) 0.0013(13) 0.0201(13) -0.0052(13) _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 1.232(3) . ? O2 C3 1.410(3) . ? O2 C4 1.424(3) . ? O3 C5 1.424(3) . ? O3 C9 1.452(3) . ? N1 C1 1.344(3) . ? N1 C5 1.458(3) . ? N1 H1 0.8800 . ? C1 C2 1.498(3) . ? C2 C3 1.523(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.565(3) . ? C3 H3 1.0000 . ? C4 H4B 0.9800 . ? C4 H4A 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.525(3) . ? C6 C7 1.526(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.529(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.514(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.516(4) . ? C9 H9 1.0000 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? 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 C3 O2 C4 114.4(2) . . ? C5 O3 C9 113.92(18) . . ? C1 N1 C5 115.1(2) . . ? C1 N1 H1 122.4 . . ? C5 N1 H1 122.4 . . ? O1 C1 N1 125.1(2) . . ? O1 C1 C2 126.3(2) . . ? N1 C1 C2 108.6(2) . . ? C1 C2 C3 104.9(2) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? O2 C3 C2 108.5(2) . . ? O2 C3 C5 116.17(19) . . ? C2 C3 C5 104.71(19) . . ? O2 C3 H3 109.1 . . ? C2 C3 H3 109.1 . . ? C5 C3 H3 109.1 . . ? O2 C4 H4B 109.5 . . ? O2 C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? O2 C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? O3 C5 N1 111.22(19) . . ? O3 C5 C6 111.09(18) . . ? N1 C5 C6 111.1(2) . . ? O3 C5 C3 107.49(18) . . ? N1 C5 C3 101.54(18) . . ? C6 C5 C3 114.0(2) . . ? C5 C6 C7 111.7(2) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 109.1(2) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 110.5(2) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O3 C9 C8 111.4(2) . . ? O3 C9 C10 105.5(2) . . ? C8 C9 C10 113.3(2) . . ? O3 C9 H9 108.8 . . ? C8 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 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 C5 N1 C1 O1 175.8(2) . . . . ? C5 N1 C1 C2 -4.1(3) . . . . ? O1 C1 C2 C3 169.2(2) . . . . ? N1 C1 C2 C3 -11.0(3) . . . . ? C4 O2 C3 C2 173.4(2) . . . . ? C4 O2 C3 C5 -69.1(3) . . . . ? C1 C2 C3 O2 145.0(2) . . . . ? C1 C2 C3 C5 20.4(2) . . . . ? C9 O3 C5 N1 -68.3(2) . . . . ? C9 O3 C5 C6 56.1(3) . . . . ? C9 O3 C5 C3 -178.61(19) . . . . ? C1 N1 C5 O3 -97.4(2) . . . . ? C1 N1 C5 C6 138.2(2) . . . . ? C1 N1 C5 C3 16.7(3) . . . . ? O2 C3 C5 O3 -24.7(3) . . . . ? C2 C3 C5 O3 95.0(2) . . . . ? O2 C3 C5 N1 -141.5(2) . . . . ? C2 C3 C5 N1 -21.9(2) . . . . ? O2 C3 C5 C6 98.9(2) . . . . ? C2 C3 C5 C6 -141.5(2) . . . . ? O3 C5 C6 C7 -54.4(3) . . . . ? N1 C5 C6 C7 70.0(2) . . . . ? C3 C5 C6 C7 -176.05(19) . . . . ? C5 C6 C7 C8 53.7(3) . . . . ? C6 C7 C8 C9 -54.2(3) . . . . ? C5 O3 C9 C8 -57.5(3) . . . . ? C5 O3 C9 C10 179.1(2) . . . . ? C7 C8 C9 O3 55.8(3) . . . . ? C7 C8 C9 C10 174.6(2) . . . . ? 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 N1 H1 O1 0.88 2.03 2.889(3) 164.3 7_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.053 data_sa1523 _database_code_depnum_ccdc_archive 'CCDC 919544' #TrackingRef 'web_deposit_cif_file_3_guangli_1358151266.sa1523.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H17 N O3' _chemical_formula_sum 'C10 H17 N O3' _chemical_formula_weight 199.25 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)/n 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 11.044(3) _cell_length_b 8.0060(19) _cell_length_c 11.730(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.346(4) _cell_angle_gamma 90.00 _cell_volume 1026.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3523 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5182 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2344 _reflns_number_gt 2150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Olex2 ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0425P)^2^+0.4024P] 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 2344 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 0.97386(10) 0.47983(15) 0.33728(9) 0.0328(3) Uani 1 1 d . . . O2 O 0.60054(10) 0.40871(14) 0.34545(9) 0.0303(3) Uani 1 1 d . . . O3 O 0.80502(9) 0.10587(13) 0.50278(9) 0.0256(3) Uani 1 1 d . . . N1 N 0.86166(11) 0.37611(16) 0.47113(10) 0.0257(3) Uani 1 1 d . . . H1 H 0.9057 0.4208 0.5320 0.031 Uiso 1 1 calc R . . C1 C 0.88679(13) 0.39972(18) 0.36361(12) 0.0246(3) Uani 1 1 d . . . C2 C 0.78908(13) 0.3125(2) 0.28101(12) 0.0265(3) Uani 1 1 d . . . H2B H 0.8208 0.2075 0.2519 0.032 Uiso 1 1 calc R . . H2A H 0.7590 0.3854 0.2148 0.032 Uiso 1 1 calc R . . C3 C 0.68739(12) 0.27672(18) 0.35375(11) 0.0226(3) Uani 1 1 d . . . H3 H 0.6467 0.1674 0.3320 0.027 Uiso 1 1 calc R . . C4 C 0.75685(13) 0.27179(18) 0.47893(12) 0.0227(3) Uani 1 1 d . . . C5 C 0.68654(14) 0.3323(2) 0.57317(12) 0.0275(3) Uani 1 1 d . . . H5A H 0.6464 0.4401 0.5497 0.033 Uiso 1 1 calc R . . H5B H 0.7444 0.3514 0.6447 0.033 Uiso 1 1 calc R . . C6 C 0.58995(15) 0.2062(2) 0.59670(14) 0.0327(4) Uani 1 1 d . . . H6B H 0.5504 0.2442 0.6627 0.039 Uiso 1 1 calc R . . H6A H 0.5261 0.1970 0.5284 0.039 Uiso 1 1 calc R . . C7 C 0.64955(15) 0.0376(2) 0.62357(13) 0.0333(4) Uani 1 1 d . . . H7A H 0.5862 -0.0458 0.6350 0.040 Uiso 1 1 calc R . . H7B H 0.7081 0.0449 0.6958 0.040 Uiso 1 1 calc R . . C8 C 0.71644(14) -0.01809(19) 0.52586(13) 0.0276(3) Uani 1 1 d . . . H8 H 0.6551 -0.0322 0.4549 0.033 Uiso 1 1 calc R . . C9 C 0.51382(15) 0.3990(2) 0.24312(15) 0.0365(4) Uani 1 1 d . . . H9C H 0.5544 0.4247 0.1763 0.055 Uiso 1 1 calc R . . H9B H 0.4479 0.4796 0.2475 0.055 Uiso 1 1 calc R . . H9A H 0.4795 0.2860 0.2352 0.055 Uiso 1 1 calc R . . C10 C 0.78554(18) -0.1806(2) 0.54926(15) 0.0399(4) Uani 1 1 d . . . H10C H 0.8433 -0.1706 0.6207 0.060 Uiso 1 1 calc R . . H10B H 0.8305 -0.2054 0.4851 0.060 Uiso 1 1 calc R . . H10A H 0.7275 -0.2711 0.5571 0.060 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 0.0295(6) 0.0386(7) 0.0309(6) 0.0037(5) 0.0065(4) -0.0113(5) O2 0.0285(6) 0.0298(6) 0.0309(6) -0.0032(4) -0.0019(4) 0.0065(5) O3 0.0242(5) 0.0238(6) 0.0286(5) 0.0031(4) 0.0029(4) -0.0030(4) N1 0.0251(6) 0.0284(7) 0.0230(6) 0.0002(5) 0.0014(5) -0.0095(5) C1 0.0240(7) 0.0237(7) 0.0262(7) 0.0029(6) 0.0037(5) -0.0011(6) C2 0.0279(7) 0.0286(8) 0.0234(7) -0.0003(6) 0.0048(5) -0.0026(6) C3 0.0221(7) 0.0214(7) 0.0238(6) -0.0016(5) 0.0021(5) -0.0009(5) C4 0.0225(7) 0.0223(7) 0.0231(6) -0.0003(5) 0.0026(5) -0.0040(6) C5 0.0303(7) 0.0285(8) 0.0244(7) -0.0048(6) 0.0060(6) -0.0059(6) C6 0.0315(8) 0.0386(9) 0.0302(7) -0.0057(7) 0.0120(6) -0.0100(7) C7 0.0386(9) 0.0345(9) 0.0278(8) 0.0011(6) 0.0078(6) -0.0148(7) C8 0.0330(8) 0.0244(7) 0.0250(7) 0.0023(6) 0.0024(6) -0.0079(6) C9 0.0305(8) 0.0364(9) 0.0391(9) 0.0004(7) -0.0063(7) 0.0069(7) C10 0.0515(11) 0.0260(8) 0.0402(9) 0.0047(7) 0.0000(8) -0.0027(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2318(17) . ? O2 C3 1.4209(17) . ? O2 C9 1.4248(18) . ? O3 C4 1.4431(18) . ? O3 C8 1.4464(17) . ? N1 C1 1.3435(18) . ? N1 C4 1.4410(18) . ? N1 H1 0.8800 . ? C1 C2 1.512(2) . ? C2 C3 1.5328(19) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.5553(19) . ? C3 H3 1.0000 . ? C4 C5 1.520(2) . ? C5 C6 1.523(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.515(2) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 C8 1.518(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.513(2) . ? C8 H8 1.0000 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C9 H9A 0.9800 . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? C10 H10A 0.9800 . ? 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 C3 O2 C9 112.43(11) . . ? C4 O3 C8 115.32(11) . . ? C1 N1 C4 114.73(12) . . ? C1 N1 H1 122.6 . . ? C4 N1 H1 122.6 . . ? O1 C1 N1 125.71(13) . . ? O1 C1 C2 126.16(13) . . ? N1 C1 C2 108.12(12) . . ? C1 C2 C3 104.00(11) . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? H2B C2 H2A 109.0 . . ? O2 C3 C2 111.39(12) . . ? O2 C3 C4 108.61(11) . . ? C2 C3 C4 103.26(11) . . ? O2 C3 H3 111.1 . . ? C2 C3 H3 111.1 . . ? C4 C3 H3 111.1 . . ? N1 C4 O3 105.60(11) . . ? N1 C4 C5 111.18(12) . . ? O3 C4 C5 111.43(12) . . ? N1 C4 C3 102.48(11) . . ? O3 C4 C3 108.90(11) . . ? C5 C4 C3 116.39(12) . . ? C4 C5 C6 111.46(12) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 109.51(13) . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? H6B C6 H6A 108.2 . . ? C6 C7 C8 110.42(13) . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O3 C8 C10 106.68(13) . . ? O3 C8 C7 110.88(12) . . ? C10 C8 C7 113.79(14) . . ? O3 C8 H8 108.4 . . ? C10 C8 H8 108.4 . . ? C7 C8 H8 108.4 . . ? O2 C9 H9C 109.5 . . ? O2 C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? O2 C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? C8 C10 H10C 109.5 . . ? C8 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C8 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? H10B C10 H10A 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 -177.67(14) . . . . ? C4 N1 C1 C2 2.90(17) . . . . ? O1 C1 C2 C3 -164.74(15) . . . . ? N1 C1 C2 C3 14.70(15) . . . . ? C9 O2 C3 C2 80.59(15) . . . . ? C9 O2 C3 C4 -166.34(12) . . . . ? C1 C2 C3 O2 91.53(13) . . . . ? C1 C2 C3 C4 -24.86(14) . . . . ? C1 N1 C4 O3 95.15(14) . . . . ? C1 N1 C4 C5 -143.85(13) . . . . ? C1 N1 C4 C3 -18.82(16) . . . . ? C8 O3 C4 N1 174.00(10) . . . . ? C8 O3 C4 C5 53.16(15) . . . . ? C8 O3 C4 C3 -76.57(14) . . . . ? O2 C3 C4 N1 -92.24(13) . . . . ? C2 C3 C4 N1 26.10(14) . . . . ? O2 C3 C4 O3 156.24(11) . . . . ? C2 C3 C4 O3 -85.42(13) . . . . ? O2 C3 C4 C5 29.29(16) . . . . ? C2 C3 C4 C5 147.63(13) . . . . ? N1 C4 C5 C6 -169.72(12) . . . . ? O3 C4 C5 C6 -52.21(16) . . . . ? C3 C4 C5 C6 73.47(17) . . . . ? C4 C5 C6 C7 54.65(16) . . . . ? C5 C6 C7 C8 -56.36(16) . . . . ? C4 O3 C8 C10 -179.58(12) . . . . ? C4 O3 C8 C7 -55.17(16) . . . . ? C6 C7 C8 O3 56.00(16) . . . . ? C6 C7 C8 C10 176.25(13) . . . . ? 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 N1 H1 O1 0.88 2.04 2.9146(17) 172.9 3_766 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.249 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.040 data_a4 _database_code_depnum_ccdc_archive 'CCDC 919545' #TrackingRef 'web_deposit_cif_file_4_guangli_1358151266.A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 N2 O2' _chemical_formula_sum 'C14 H20 N2 O2' _chemical_formula_weight 248.32 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 orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.663(3) _cell_length_b 8.2891(17) _cell_length_c 21.056(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2733.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10122 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9483 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2396 _reflns_number_gt 2066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELX97 (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^ > 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^)+(0.0253P)^2^+1.9630P] 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 2396 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.245 _refine_ls_restrained_S_all 1.245 _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 0.59644(10) 0.4975(2) 0.37348(8) 0.0275(4) Uani 1 1 d . . . O2 O 0.69237(13) 0.6293(2) 0.46341(9) 0.0429(6) Uani 1 1 d . . . N1 N 0.56623(13) 0.7524(2) 0.32818(10) 0.0242(5) Uani 1 1 d . . . N2 N 0.59898(13) 0.9061(2) 0.20759(10) 0.0267(5) Uani 1 1 d . . . H2 H 0.5484 0.8601 0.2074 0.032 Uiso 1 1 calc R . . C1 C 0.57509(16) 0.6610(3) 0.38838(12) 0.0257(6) Uani 1 1 d . . . C2 C 0.52935(16) 0.4103(3) 0.34152(13) 0.0288(6) Uani 1 1 d . . . H2A H 0.5152 0.4671 0.3010 0.035 Uiso 1 1 calc R . . C3 C 0.45003(17) 0.4032(3) 0.38265(13) 0.0327(7) Uani 1 1 d . . . H3B H 0.4622 0.3396 0.4214 0.039 Uiso 1 1 calc R . . H3A H 0.4036 0.3485 0.3591 0.039 Uiso 1 1 calc R . . C4 C 0.42148(17) 0.5722(3) 0.40125(14) 0.0352(7) Uani 1 1 d . . . H4A H 0.3990 0.6288 0.3634 0.042 Uiso 1 1 calc R . . H4B H 0.3749 0.5649 0.4329 0.042 Uiso 1 1 calc R . . C5 C 0.49516(18) 0.6674(3) 0.42892(13) 0.0328(7) Uani 1 1 d . . . H5B H 0.5086 0.6246 0.4717 0.039 Uiso 1 1 calc R . . H5A H 0.4774 0.7814 0.4339 0.039 Uiso 1 1 calc R . . C6 C 0.65402(17) 0.7360(3) 0.41979(13) 0.0308(7) Uani 1 1 d . . . H6 H 0.6358 0.8351 0.4432 0.037 Uiso 1 1 calc R . . C7 C 0.70841(16) 0.7870(3) 0.36374(13) 0.0317(7) Uani 1 1 d . . . H7B H 0.7403 0.8876 0.3727 0.038 Uiso 1 1 calc R . . H7A H 0.7489 0.7012 0.3510 0.038 Uiso 1 1 calc R . . C8 C 0.64038(15) 0.8129(3) 0.31436(13) 0.0239(6) Uani 1 1 d . . . C9 C 0.65707(15) 0.8975(3) 0.25616(13) 0.0247(6) Uani 1 1 d . . . C10 C 0.72797(16) 0.9849(3) 0.23779(14) 0.0309(7) Uani 1 1 d . . . H10 H 0.7787 0.9995 0.2618 0.037 Uiso 1 1 calc R . . C11 C 0.71157(17) 1.0485(3) 0.17727(14) 0.0351(7) Uani 1 1 d . . . H11 H 0.7486 1.1148 0.1529 0.042 Uiso 1 1 calc R . . C12 C 0.63166(17) 0.9964(3) 0.16014(14) 0.0329(7) Uani 1 1 d . . . H12 H 0.6038 1.0201 0.1212 0.039 Uiso 1 1 calc R . . C13 C 0.56531(19) 0.2459(3) 0.32608(16) 0.0423(8) Uani 1 1 d . . . H13C H 0.5835 0.1926 0.3654 0.063 Uiso 1 1 calc R . . H13B H 0.6144 0.2578 0.2976 0.063 Uiso 1 1 calc R . . H13A H 0.5213 0.1805 0.3052 0.063 Uiso 1 1 calc R . . C14 C 0.7541(2) 0.7080(4) 0.50177(17) 0.0609(11) Uani 1 1 d . . . H14C H 0.7785 0.6306 0.5319 0.091 Uiso 1 1 calc R . . H14A H 0.7269 0.7963 0.5252 0.091 Uiso 1 1 calc R . . H14B H 0.7996 0.7514 0.4747 0.091 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 0.0251(10) 0.0242(9) 0.0331(11) -0.0016(8) -0.0064(8) -0.0022(8) O2 0.0493(13) 0.0379(11) 0.0413(13) 0.0081(10) -0.0247(11) -0.0107(10) N1 0.0234(11) 0.0240(11) 0.0254(13) -0.0018(9) -0.0009(10) 0.0006(9) N2 0.0216(11) 0.0278(12) 0.0308(13) 0.0020(10) 0.0023(10) -0.0016(9) C1 0.0284(14) 0.0234(13) 0.0252(15) 0.0002(11) -0.0046(12) -0.0002(11) C2 0.0266(14) 0.0312(14) 0.0286(16) -0.0035(12) -0.0047(12) -0.0051(12) C3 0.0325(15) 0.0341(15) 0.0316(17) 0.0005(13) -0.0025(13) -0.0069(12) C4 0.0282(15) 0.0393(16) 0.0383(18) 0.0050(14) 0.0088(13) -0.0015(12) C5 0.0426(17) 0.0292(14) 0.0267(17) 0.0006(13) 0.0023(13) 0.0005(13) C6 0.0353(15) 0.0271(14) 0.0301(16) 0.0009(12) -0.0077(13) -0.0006(12) C7 0.0257(14) 0.0261(14) 0.0433(18) -0.0016(13) -0.0086(13) -0.0020(11) C8 0.0225(13) 0.0192(12) 0.0301(15) -0.0038(11) -0.0025(12) 0.0016(11) C9 0.0209(13) 0.0227(13) 0.0305(16) -0.0028(12) 0.0003(12) 0.0013(10) C10 0.0214(14) 0.0298(14) 0.0416(18) -0.0045(13) -0.0001(12) -0.0013(11) C11 0.0301(15) 0.0337(15) 0.0414(19) 0.0050(14) 0.0104(13) -0.0043(12) C12 0.0357(16) 0.0348(15) 0.0282(16) 0.0045(13) 0.0049(13) -0.0005(13) C13 0.0378(17) 0.0356(16) 0.054(2) -0.0141(15) 0.0007(15) -0.0055(14) C14 0.068(2) 0.058(2) 0.057(2) 0.0080(19) -0.037(2) -0.0184(19) _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 1.431(3) . ? O1 C2 1.442(3) . ? O2 C6 1.410(3) . ? O2 C14 1.419(3) . ? N1 C8 1.298(3) . ? N1 C1 1.483(3) . ? N2 C12 1.349(3) . ? N2 C9 1.371(3) . ? N2 H2 0.8800 . ? C1 C5 1.516(4) . ? C1 C6 1.534(3) . ? C2 C13 1.510(4) . ? C2 C3 1.515(4) . ? C2 H2A 1.0000 . ? C3 C4 1.522(4) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C5 1.515(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 C7 1.516(4) . ? C6 H6 1.0000 . ? C7 C8 1.504(3) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C8 C9 1.436(4) . ? C9 C10 1.381(3) . ? C10 C11 1.403(4) . ? C10 H10 0.9500 . ? C11 C12 1.372(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13C 0.9800 . ? C13 H13B 0.9800 . ? C13 H13A 0.9800 . ? C14 H14C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? 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 C1 O1 C2 114.02(18) . . ? C6 O2 C14 111.9(2) . . ? C8 N1 C1 107.8(2) . . ? C12 N2 C9 109.2(2) . . ? C12 N2 H2 125.4 . . ? C9 N2 H2 125.4 . . ? O1 C1 N1 108.6(2) . . ? O1 C1 C5 110.5(2) . . ? N1 C1 C5 112.7(2) . . ? O1 C1 C6 106.8(2) . . ? N1 C1 C6 103.7(2) . . ? C5 C1 C6 114.1(2) . . ? O1 C2 C13 106.3(2) . . ? O1 C2 C3 110.5(2) . . ? C13 C2 C3 113.2(2) . . ? O1 C2 H2A 108.9 . . ? C13 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C2 C3 C4 110.6(2) . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? H3B C3 H3A 108.1 . . ? C5 C4 C3 110.8(2) . . ? 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 . . ? C4 C5 C1 113.2(2) . . ? C4 C5 H5B 108.9 . . ? C1 C5 H5B 108.9 . . ? C4 C5 H5A 108.9 . . ? C1 C5 H5A 108.9 . . ? H5B C5 H5A 107.7 . . ? O2 C6 C7 116.3(2) . . ? O2 C6 C1 111.7(2) . . ? C7 C6 C1 103.3(2) . . ? O2 C6 H6 108.4 . . ? C7 C6 H6 108.4 . . ? C1 C6 H6 108.4 . . ? C8 C7 C6 100.4(2) . . ? C8 C7 H7B 111.7 . . ? C6 C7 H7B 111.7 . . ? C8 C7 H7A 111.7 . . ? C6 C7 H7A 111.7 . . ? H7B C7 H7A 109.5 . . ? N1 C8 C9 122.9(2) . . ? N1 C8 C7 115.1(2) . . ? C9 C8 C7 122.0(2) . . ? N2 C9 C10 107.3(2) . . ? N2 C9 C8 122.8(2) . . ? C10 C9 C8 129.9(2) . . ? C9 C10 C11 107.7(2) . . ? C9 C10 H10 126.1 . . ? C11 C10 H10 126.1 . . ? C12 C11 C10 106.7(2) . . ? C12 C11 H11 126.6 . . ? C10 C11 H11 126.6 . . ? N2 C12 C11 109.0(3) . . ? N2 C12 H12 125.5 . . ? C11 C12 H12 125.5 . . ? C2 C13 H13C 109.5 . . ? C2 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? C2 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? O2 C14 H14C 109.5 . . ? O2 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? H14A C14 H14B 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 C2 O1 C1 N1 -66.9(2) . . . . ? C2 O1 C1 C5 57.2(3) . . . . ? C2 O1 C1 C6 -178.1(2) . . . . ? C8 N1 C1 O1 -90.7(2) . . . . ? C8 N1 C1 C5 146.6(2) . . . . ? C8 N1 C1 C6 22.7(3) . . . . ? C1 O1 C2 C13 176.4(2) . . . . ? C1 O1 C2 C3 -60.4(3) . . . . ? O1 C2 C3 C4 55.9(3) . . . . ? C13 C2 C3 C4 175.1(2) . . . . ? C2 C3 C4 C5 -51.0(3) . . . . ? C3 C4 C5 C1 49.4(3) . . . . ? O1 C1 C5 C4 -51.3(3) . . . . ? N1 C1 C5 C4 70.3(3) . . . . ? C6 C1 C5 C4 -171.7(2) . . . . ? C14 O2 C6 C7 73.7(3) . . . . ? C14 O2 C6 C1 -168.0(3) . . . . ? O1 C1 C6 O2 -42.2(3) . . . . ? N1 C1 C6 O2 -156.8(2) . . . . ? C5 C1 C6 O2 80.2(3) . . . . ? O1 C1 C6 C7 83.6(2) . . . . ? N1 C1 C6 C7 -31.0(2) . . . . ? C5 C1 C6 C7 -154.0(2) . . . . ? O2 C6 C7 C8 149.8(2) . . . . ? C1 C6 C7 C8 27.0(2) . . . . ? C1 N1 C8 C9 174.5(2) . . . . ? C1 N1 C8 C7 -5.1(3) . . . . ? C6 C7 C8 N1 -14.8(3) . . . . ? C6 C7 C8 C9 165.6(2) . . . . ? C12 N2 C9 C10 -0.2(3) . . . . ? C12 N2 C9 C8 178.5(2) . . . . ? N1 C8 C9 N2 -7.3(4) . . . . ? C7 C8 C9 N2 172.3(2) . . . . ? N1 C8 C9 C10 171.1(3) . . . . ? C7 C8 C9 C10 -9.4(4) . . . . ? N2 C9 C10 C11 0.6(3) . . . . ? C8 C9 C10 C11 -178.0(2) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C9 N2 C12 C11 -0.2(3) . . . . ? C10 C11 C12 N2 0.6(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 N2 H2 N1 0.88 2.71 2.887(3) 92.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.186 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.046