# Supplementary Material (ESI) for Green Chemistry # This journal is © 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_author_name 'Ching Fa Yao' _publ_contact_author_name 'Mustafa Raihan' _publ_contact_author_email mustafajr@gmail.com data_9972 _database_code_depnum_ccdc_archive 'CCDC 751947' #Author Ching Fa Yao #expected journal for publication OBC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 N O2' _chemical_formula_sum 'C20 H15 N O2' _chemical_formula_weight 301.33 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 'C 2/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 22.0450(3) _cell_length_b 9.2680(2) _cell_length_c 17.8038(4) _cell_angle_alpha 90.00 _cell_angle_beta 124.7510(10) _cell_angle_gamma 90.00 _cell_volume 2988.74(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7801 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.797 _exptl_absorpt_correction_T_max 1.0842 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12770 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2632 _reflns_number_gt 1848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0845P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2632 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.40498(7) -0.14201(12) 0.04257(8) 0.0649(4) Uani 1 1 d . . . O2 O 0.15926(7) -0.03670(13) -0.16236(9) 0.0633(4) Uani 1 1 d . . . N1 N 0.35436(8) -0.25270(14) -0.01474(10) 0.0582(4) Uani 1 1 d . . . C1 C 0.29210(9) -0.19277(18) -0.07302(10) 0.0451(4) Uani 1 1 d . . . C2 C 0.22331(9) -0.26326(17) -0.14219(10) 0.0444(4) Uani 1 1 d . . . C3 C 0.21673(9) -0.41013(18) -0.17248(10) 0.0458(4) Uani 1 1 d . . . C4 C 0.27774(11) -0.50355(18) -0.13872(12) 0.0542(5) Uani 1 1 d . . . H4 H 0.3250 -0.4703 -0.0945 0.065 Uiso 1 1 calc R . . C5 C 0.26839(12) -0.6415(2) -0.16995(13) 0.0642(6) Uani 1 1 d . . . H5 H 0.3094 -0.7008 -0.1469 0.077 Uiso 1 1 calc R . . C6 C 0.19842(13) -0.6953(2) -0.23590(13) 0.0688(6) Uani 1 1 d . . . H6 H 0.1928 -0.7901 -0.2560 0.083 Uiso 1 1 calc R . . C7 C 0.13851(12) -0.6085(2) -0.27062(12) 0.0638(6) Uani 1 1 d . . . H7 H 0.0919 -0.6446 -0.3147 0.077 Uiso 1 1 calc R . . C8 C 0.14574(10) -0.46468(19) -0.24112(11) 0.0518(5) Uani 1 1 d . . . C9 C 0.08364(11) -0.3730(2) -0.27857(12) 0.0628(5) Uani 1 1 d . . . H9 H 0.0371 -0.4089 -0.3230 0.075 Uiso 1 1 calc R . . C10 C 0.09037(10) -0.2348(2) -0.25144(12) 0.0632(6) Uani 1 1 d . . . H10 H 0.0488 -0.1761 -0.2780 0.076 Uiso 1 1 calc R . . C11 C 0.16009(10) -0.17914(19) -0.18305(11) 0.0511(5) Uani 1 1 d . . . C12 C 0.22157(10) 0.01464(19) -0.07646(13) 0.0588(5) Uani 1 1 d . . . H12A H 0.2196 -0.0233 -0.0271 0.071 Uiso 1 1 calc R . . H12B H 0.2199 0.1191 -0.0747 0.071 Uiso 1 1 calc R . . C13 C 0.29260(9) -0.03191(17) -0.06337(11) 0.0476(5) Uani 1 1 d . . . H13 H 0.2977 0.0150 -0.1088 0.057 Uiso 1 1 calc R . . C14 C 0.36275(10) -0.01290(17) 0.03130(12) 0.0533(5) Uani 1 1 d . . . H14 H 0.3504 -0.0149 0.0762 0.064 Uiso 1 1 calc R . . C15 C 0.40791(9) 0.11947(17) 0.04721(11) 0.0462(4) Uani 1 1 d . . . C16 C 0.41602(10) 0.22515(19) 0.10704(12) 0.0610(5) Uani 1 1 d . . . H16 H 0.3953 0.2121 0.1397 0.073 Uiso 1 1 calc R . . C17 C 0.45441(13) 0.3494(2) 0.11862(15) 0.0735(6) Uani 1 1 d . . . H17 H 0.4590 0.4202 0.1585 0.088 Uiso 1 1 calc R . . C18 C 0.48600(12) 0.36968(19) 0.07203(14) 0.0671(6) Uani 1 1 d . . . H18 H 0.5120 0.4540 0.0803 0.080 Uiso 1 1 calc R . . C19 C 0.47926(11) 0.26527(19) 0.01286(13) 0.0610(5) Uani 1 1 d . . . H19 H 0.5011 0.2782 -0.0185 0.073 Uiso 1 1 calc R . . C20 C 0.44006(10) 0.14164(18) 0.00027(11) 0.0535(5) Uani 1 1 d . . . H20 H 0.4350 0.0718 -0.0404 0.064 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 0.0431(8) 0.0539(8) 0.0646(8) 0.0013(6) 0.0111(7) -0.0015(6) O2 0.0457(8) 0.0660(8) 0.0668(8) 0.0024(6) 0.0253(7) 0.0131(6) N1 0.0419(9) 0.0538(9) 0.0580(9) 0.0020(7) 0.0160(8) -0.0034(7) C1 0.0376(10) 0.0512(10) 0.0458(10) 0.0061(7) 0.0233(9) 0.0036(8) C2 0.0357(10) 0.0553(10) 0.0411(9) 0.0057(7) 0.0212(8) 0.0022(8) C3 0.0449(11) 0.0548(10) 0.0395(9) 0.0043(7) 0.0251(8) -0.0019(8) C4 0.0530(12) 0.0539(11) 0.0511(10) 0.0030(8) 0.0269(10) 0.0016(9) C5 0.0720(15) 0.0576(12) 0.0642(12) 0.0025(9) 0.0396(12) 0.0052(10) C6 0.0917(18) 0.0584(12) 0.0622(13) -0.0076(10) 0.0473(13) -0.0105(12) C7 0.0668(14) 0.0739(14) 0.0483(11) -0.0106(9) 0.0314(11) -0.0184(11) C8 0.0491(12) 0.0668(12) 0.0388(9) 0.0011(8) 0.0245(9) -0.0044(9) C9 0.0428(12) 0.0870(15) 0.0451(10) -0.0060(10) 0.0171(9) -0.0092(10) C10 0.0365(12) 0.0897(15) 0.0517(11) 0.0073(10) 0.0184(10) 0.0104(10) C11 0.0461(11) 0.0584(11) 0.0483(10) 0.0061(8) 0.0265(9) 0.0059(9) C12 0.0523(12) 0.0604(12) 0.0629(12) -0.0032(9) 0.0323(10) 0.0052(9) C13 0.0436(11) 0.0505(10) 0.0471(10) 0.0033(7) 0.0250(9) 0.0013(8) C14 0.0513(12) 0.0587(11) 0.0489(11) 0.0014(8) 0.0280(10) -0.0021(9) C15 0.0420(10) 0.0524(10) 0.0414(9) 0.0009(7) 0.0221(8) 0.0018(8) C16 0.0704(14) 0.0637(13) 0.0638(12) -0.0032(9) 0.0471(11) 0.0023(10) C17 0.0959(18) 0.0568(13) 0.0776(14) -0.0151(10) 0.0552(14) -0.0071(11) C18 0.0718(15) 0.0514(11) 0.0739(13) 0.0034(10) 0.0391(12) -0.0050(10) C19 0.0638(13) 0.0626(12) 0.0639(12) 0.0088(9) 0.0406(11) 0.0001(10) C20 0.0573(12) 0.0560(11) 0.0473(10) -0.0017(8) 0.0299(10) 0.0008(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.4286(17) . ? O1 C14 1.458(2) . ? O2 C11 1.373(2) . ? O2 C12 1.434(2) . ? N1 C1 1.2826(19) . ? C1 C2 1.454(2) . ? C1 C13 1.500(2) . ? C2 C11 1.387(2) . ? C2 C3 1.441(2) . ? C3 C4 1.414(2) . ? C3 C8 1.420(2) . ? C4 C5 1.363(2) . ? C4 H4 0.9300 . ? C5 C6 1.393(3) . ? C5 H5 0.9300 . ? C6 C7 1.358(3) . ? C6 H6 0.9300 . ? C7 C8 1.408(3) . ? C7 H7 0.9300 . ? C8 C9 1.414(2) . ? C9 C10 1.347(3) . ? C9 H9 0.9300 . ? C10 C11 1.406(2) . ? C10 H10 0.9300 . ? C12 C13 1.509(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.514(2) . ? C13 H13 0.9800 . ? C14 C15 1.502(2) . ? C14 H14 0.9800 . ? C15 C20 1.385(2) . ? C15 C16 1.382(2) . ? C16 C17 1.373(2) . ? C16 H16 0.9300 . ? C17 C18 1.366(3) . ? C17 H17 0.9300 . ? C18 C19 1.375(3) . ? C18 H18 0.9300 . ? C19 C20 1.374(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 N1 O1 C14 108.27(12) . . ? C11 O2 C12 116.99(13) . . ? C1 N1 O1 107.87(13) . . ? N1 C1 C2 127.52(16) . . ? N1 C1 C13 113.78(14) . . ? C2 C1 C13 118.66(14) . . ? C11 C2 C3 118.56(15) . . ? C11 C2 C1 116.28(16) . . ? C3 C2 C1 125.13(15) . . ? C4 C3 C8 117.55(16) . . ? C4 C3 C2 123.44(16) . . ? C8 C3 C2 119.00(16) . . ? C5 C4 C3 121.02(18) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 119.60(19) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 121.15(19) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C9 121.31(18) . . ? C7 C8 C3 119.53(18) . . ? C9 C8 C3 119.16(17) . . ? C10 C9 C8 121.55(17) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 120.13(18) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? O2 C11 C2 124.23(16) . . ? O2 C11 C10 114.20(16) . . ? C2 C11 C10 121.57(17) . . ? O2 C12 C13 110.41(14) . . ? O2 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? O2 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C1 C13 C12 109.11(14) . . ? C1 C13 C14 100.33(13) . . ? C12 C13 C14 116.77(15) . . ? C1 C13 H13 110.1 . . ? C12 C13 H13 110.1 . . ? C14 C13 H13 110.1 . . ? O1 C14 C15 110.00(14) . . ? O1 C14 C13 102.98(12) . . ? C15 C14 C13 116.86(14) . . ? O1 C14 H14 108.9 . . ? C15 C14 H14 108.9 . . ? C13 C14 H14 108.9 . . ? C20 C15 C16 118.31(16) . . ? C20 C15 C14 121.30(14) . . ? C16 C15 C14 120.34(16) . . ? C17 C16 C15 120.52(17) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.55(17) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.89(18) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 119.68(18) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C15 121.04(16) . . ? C19 C20 H20 119.5 . . ? C15 C20 H20 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.152 # Attachment '2.cif' data_9946 _database_code_depnum_ccdc_archive 'CCDC 751948' # Author Ching Fa Yao #expected journal for publication OBC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O6' _chemical_formula_sum 'C15 H17 N O6' _chemical_formula_weight 307.30 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 'P 21/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 7.1337(2) _cell_length_b 26.8903(9) _cell_length_c 7.6505(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.6140(10) _cell_angle_gamma 90.00 _cell_volume 1467.49(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12058 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9308 _exptl_absorpt_correction_T_max 1.0128 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9287 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2585 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1103P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2585 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1623 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.006 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 0.3499(2) 0.29437(8) 0.9017(3) 0.0764(6) Uani 1 1 d . . . O2 O -0.1101(3) 0.33620(7) 0.7465(3) 0.0789(6) Uani 1 1 d . . . O3 O -0.0590(3) 0.41684(9) 0.7519(4) 0.1310(11) Uani 1 1 d . . . O4 O -0.1213(2) 0.17693(7) 0.8600(2) 0.0625(5) Uani 1 1 d . . . O5 O -0.1837(2) 0.08149(7) 0.7706(2) 0.0690(6) Uani 1 1 d . . . O6 O 0.0996(3) 0.02162(8) 0.6772(3) 0.0804(6) Uani 1 1 d . . . N1 N 0.3888(3) 0.24485(10) 0.8470(3) 0.0677(7) Uani 1 1 d . . . C1 C 0.1478(4) 0.30052(11) 0.9068(3) 0.0684(8) Uani 1 1 d . . . H1 H 0.1143 0.3212 1.0072 0.082 Uiso 1 1 calc R . . C2 C 0.0862(4) 0.32588(12) 0.7396(4) 0.0819(9) Uani 1 1 d . . . H2A H 0.1553 0.3566 0.7250 0.098 Uiso 1 1 calc R . . H2B H 0.1121 0.3045 0.6405 0.098 Uiso 1 1 calc R . . C3 C -0.1665(4) 0.38340(11) 0.7553(4) 0.0675(8) Uani 1 1 d . . . C4 C -0.3723(4) 0.38782(11) 0.7687(4) 0.0789(9) Uani 1 1 d . . . H4A H -0.4278 0.3553 0.7637 0.118 Uiso 1 1 calc R . . H4B H -0.4196 0.4076 0.6736 0.118 Uiso 1 1 calc R . . H4C H -0.4033 0.4034 0.8776 0.118 Uiso 1 1 calc R . . C5 C 0.0758(3) 0.24802(10) 0.9337(3) 0.0584(7) Uani 1 1 d . . . H5 H 0.0660 0.2415 1.0593 0.070 Uiso 1 1 calc R . . C6 C -0.1010(3) 0.22981(10) 0.8422(3) 0.0604(7) Uani 1 1 d . . . H6A H -0.2091 0.2462 0.8919 0.072 Uiso 1 1 calc R . . H6B H -0.0960 0.2384 0.7192 0.072 Uiso 1 1 calc R . . C7 C 0.0308(3) 0.14862(11) 0.8141(3) 0.0559(7) Uani 1 1 d . . . C8 C -0.0031(3) 0.09923(11) 0.7715(3) 0.0579(7) Uani 1 1 d . . . C9 C -0.2260(4) 0.04904(13) 0.9124(4) 0.0839(9) Uani 1 1 d . . . H9A H -0.3536 0.0380 0.9018 0.126 Uiso 1 1 calc R . . H9B H -0.2092 0.0665 1.0209 0.126 Uiso 1 1 calc R . . H9C H -0.1437 0.0208 0.9097 0.126 Uiso 1 1 calc R . . C10 C 0.1466(4) 0.06900(12) 0.7237(3) 0.0646(7) Uani 1 1 d . . . C11 C 0.2446(4) -0.00915(13) 0.6080(4) 0.0907(10) Uani 1 1 d . . . H11A H 0.1941 -0.0413 0.5795 0.136 Uiso 1 1 calc R . . H11B H 0.3431 -0.0128 0.6935 0.136 Uiso 1 1 calc R . . H11C H 0.2939 0.0060 0.5045 0.136 Uiso 1 1 calc R . . C12 C 0.3291(4) 0.08786(12) 0.7227(3) 0.0696(8) Uani 1 1 d . . . H12 H 0.4287 0.0676 0.6906 0.084 Uiso 1 1 calc R . . C13 C 0.3604(3) 0.13613(12) 0.7690(3) 0.0661(8) Uani 1 1 d . . . H13 H 0.4826 0.1482 0.7718 0.079 Uiso 1 1 calc R . . C14 C 0.2136(3) 0.16784(10) 0.8123(3) 0.0571(7) Uani 1 1 d . . . C15 C 0.2387(3) 0.21930(11) 0.8626(3) 0.0587(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 O1 0.0489(11) 0.0960(16) 0.0844(14) 0.0071(11) 0.0016(9) -0.0117(10) O2 0.0564(12) 0.0702(14) 0.1103(16) 0.0086(11) 0.0052(10) -0.0044(10) O3 0.0912(18) 0.0780(17) 0.224(3) -0.0181(17) 0.0328(18) -0.0305(14) O4 0.0369(9) 0.0750(13) 0.0758(12) 0.0020(9) 0.0115(8) 0.0032(8) O5 0.0406(10) 0.0869(14) 0.0793(13) 0.0030(10) -0.0066(8) 0.0010(9) O6 0.0555(11) 0.0914(16) 0.0942(14) -0.0125(11) -0.0001(10) 0.0175(11) N1 0.0413(12) 0.097(2) 0.0651(14) 0.0096(12) 0.0032(10) -0.0040(12) C1 0.0506(16) 0.090(2) 0.0646(17) -0.0043(15) 0.0111(13) -0.0099(14) C2 0.0594(18) 0.093(2) 0.093(2) 0.0209(17) 0.0165(16) -0.0031(16) C3 0.0701(18) 0.066(2) 0.0662(17) -0.0001(14) 0.0045(13) -0.0095(16) C4 0.0672(19) 0.085(2) 0.084(2) -0.0065(16) -0.0069(15) 0.0010(16) C5 0.0464(13) 0.0809(19) 0.0481(14) 0.0031(12) 0.0067(11) -0.0049(13) C6 0.0430(14) 0.077(2) 0.0614(16) 0.0021(13) 0.0058(11) 0.0009(12) C7 0.0364(13) 0.082(2) 0.0493(14) 0.0075(13) 0.0045(10) 0.0066(13) C8 0.0396(13) 0.081(2) 0.0528(15) 0.0038(13) -0.0010(11) 0.0041(13) C9 0.0585(18) 0.102(2) 0.091(2) 0.0130(19) 0.0024(15) -0.0041(16) C10 0.0543(16) 0.083(2) 0.0564(15) -0.0020(14) -0.0036(12) 0.0117(14) C11 0.073(2) 0.096(2) 0.103(2) -0.0119(18) 0.0038(17) 0.0316(17) C12 0.0448(15) 0.099(2) 0.0648(18) 0.0001(15) 0.0029(13) 0.0145(15) C13 0.0383(13) 0.102(2) 0.0584(16) 0.0099(15) 0.0039(11) 0.0046(14) C14 0.0377(13) 0.088(2) 0.0458(14) 0.0057(13) 0.0035(10) 0.0024(13) C15 0.0384(13) 0.093(2) 0.0450(14) 0.0116(13) 0.0008(10) -0.0011(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 N1 1.424(3) . ? O1 C1 1.452(3) . ? O2 C3 1.333(3) . ? O2 C2 1.429(3) . ? O3 C3 1.182(3) . ? O4 C7 1.374(3) . ? O4 C6 1.436(3) . ? O5 C8 1.374(3) . ? O5 C9 1.427(3) . ? O6 C10 1.364(3) . ? O6 C11 1.431(3) . ? N1 C15 1.279(3) . ? C1 C5 1.517(4) . ? C1 C2 1.511(4) . ? C1 H1 0.9800 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.478(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C15 1.502(3) . ? C5 C6 1.517(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.388(4) . ? C7 C14 1.403(3) . ? C8 C10 1.394(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C12 1.397(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.363(4) . ? C12 H12 0.9300 . ? C13 C14 1.393(4) . ? C13 H13 0.9300 . ? C14 C15 1.447(4) . ? 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 N1 O1 C1 108.13(18) . . ? C3 O2 C2 118.9(2) . . ? C7 O4 C6 116.35(18) . . ? C8 O5 C9 114.47(19) . . ? C10 O6 C11 117.4(2) . . ? C15 N1 O1 108.0(2) . . ? O1 C1 C5 103.6(2) . . ? O1 C1 C2 108.0(2) . . ? C5 C1 C2 116.1(2) . . ? O1 C1 H1 109.6 . . ? C5 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? O2 C2 C1 109.4(2) . . ? O2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O3 C3 O2 121.8(3) . . ? O3 C3 C4 125.8(3) . . ? O2 C3 C4 112.4(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C15 C5 C1 99.5(2) . . ? C15 C5 C6 108.0(2) . . ? C1 C5 C6 121.2(2) . . ? C15 C5 H5 109.1 . . ? C1 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? O4 C6 C5 111.1(2) . . ? O4 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O4 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O4 C7 C8 117.0(2) . . ? O4 C7 C14 122.3(2) . . ? C8 C7 C14 120.6(2) . . ? O5 C8 C7 119.6(2) . . ? O5 C8 C10 121.2(3) . . ? C7 C8 C10 119.2(2) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O6 C10 C12 124.4(2) . . ? O6 C10 C8 115.2(2) . . ? C12 C10 C8 120.4(3) . . ? O6 C11 H11A 109.5 . . ? O6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C10 119.6(2) . . ? C13 C12 H12 120.2 . . ? C10 C12 H12 120.2 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C7 118.6(3) . . ? C13 C14 C15 123.9(2) . . ? C7 C14 C15 117.5(2) . . ? N1 C15 C14 126.1(2) . . ? N1 C15 C5 114.2(2) . . ? C14 C15 C5 119.6(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.258 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.061 # Attachment '3.cif' data_10043 _database_code_depnum_ccdc_archive 'CCDC 751949' #Author Ching Fa Yao #expected journal for publication OBC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O2' _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 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 'P c a b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 9.1168(3) _cell_length_b 13.8294(4) _cell_length_c 17.2443(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2174.16(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5438 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9384 _exptl_absorpt_correction_T_max 1.043 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10249 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1922 _reflns_number_gt 1081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0600P)^2^+0.4861P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1922 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1157 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.7502(2) 0.25062(15) 0.83359(13) 0.0833(6) Uani 1 1 d . . . O2 O 1.0538(2) 0.51586(13) 0.84583(13) 0.0799(6) Uani 1 1 d . . . N1 N 0.7075(3) 0.3342(2) 0.87691(14) 0.0766(7) Uani 1 1 d . . . C1 C 0.8154(3) 0.3930(2) 0.87596(14) 0.0576(7) Uani 1 1 d . . . C2 C 0.8210(3) 0.4876(2) 0.91149(15) 0.0619(7) Uani 1 1 d . . . C3 C 0.7163(4) 0.5241(3) 0.96212(17) 0.0887(10) Uani 1 1 d . . . H3 H 0.6335 0.4874 0.9734 0.106 Uiso 1 1 calc R . . C4 C 0.7329(5) 0.6138(4) 0.9960(2) 0.1088(13) Uani 1 1 d . . . H4 H 0.6627 0.6374 1.0302 0.131 Uiso 1 1 calc R . . C5 C 0.8556(6) 0.6678(3) 0.9781(2) 0.1092(14) Uani 1 1 d . . . H5 H 0.8672 0.7285 1.0004 0.131 Uiso 1 1 calc R . . C6 C 0.9600(4) 0.6341(2) 0.92862(19) 0.0889(10) Uani 1 1 d . . . H6 H 1.0423 0.6715 0.9178 0.107 Uiso 1 1 calc R . . C7 C 0.9438(3) 0.5441(2) 0.89421(17) 0.0668(8) Uani 1 1 d . . . C8 C 1.0267(3) 0.43668(19) 0.79276(17) 0.0633(8) Uani 1 1 d . . . H8 H 1.1224 0.4111 0.7769 0.076 Uiso 1 1 calc R . . C9 C 0.9462(3) 0.35629(17) 0.83330(15) 0.0576(7) Uani 1 1 d . . . H9 H 1.0128 0.3250 0.8702 0.069 Uiso 1 1 calc R . . C10 C 0.8725(3) 0.27954(18) 0.78471(16) 0.0657(8) Uani 1 1 d . . . H10 H 0.9390 0.2249 0.7763 0.079 Uiso 1 1 calc R . . C11 C 0.8134(3) 0.3157(2) 0.70842(16) 0.0733(8) Uani 1 1 d . . . H11A H 0.7208 0.3484 0.7174 0.088 Uiso 1 1 calc R . . H11B H 0.7947 0.2610 0.6747 0.088 Uiso 1 1 calc R . . C12 C 0.9178(3) 0.3846(2) 0.66821(17) 0.0840(10) Uani 1 1 d . . . H12A H 0.8745 0.4070 0.6201 0.101 Uiso 1 1 calc R . . H12B H 1.0085 0.3513 0.6560 0.101 Uiso 1 1 calc R . . C13 C 0.9498(3) 0.4706(2) 0.72051(17) 0.0749(9) Uani 1 1 d . . . H13A H 1.0111 0.5167 0.6932 0.090 Uiso 1 1 calc R . . H13B H 0.8587 0.5025 0.7343 0.090 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 0.0771(13) 0.0709(13) 0.1020(15) 0.0121(13) 0.0123(12) -0.0248(11) O2 0.0711(13) 0.0644(13) 0.1042(16) -0.0087(11) 0.0099(12) -0.0152(10) N1 0.0664(16) 0.0870(19) 0.0763(17) 0.0146(14) 0.0122(13) -0.0119(14) C1 0.0503(15) 0.0647(18) 0.0579(17) 0.0162(14) 0.0002(14) -0.0004(14) C2 0.0650(18) 0.071(2) 0.0499(15) 0.0094(15) -0.0051(14) 0.0112(15) C3 0.091(2) 0.119(3) 0.0563(18) 0.003(2) 0.0061(17) 0.031(2) C4 0.136(4) 0.135(4) 0.055(2) -0.011(2) 0.001(2) 0.055(3) C5 0.171(4) 0.093(3) 0.064(2) -0.010(2) -0.022(3) 0.035(3) C6 0.124(3) 0.068(2) 0.075(2) -0.0018(17) -0.014(2) 0.005(2) C7 0.079(2) 0.0591(19) 0.0622(17) 0.0038(15) -0.0088(16) 0.0062(16) C8 0.0503(15) 0.0508(15) 0.089(2) -0.0018(15) 0.0118(15) -0.0024(12) C9 0.0471(14) 0.0478(15) 0.0778(18) 0.0117(13) -0.0013(13) 0.0022(12) C10 0.0530(15) 0.0504(16) 0.094(2) 0.0076(15) 0.0052(16) -0.0031(13) C11 0.0691(18) 0.076(2) 0.074(2) -0.0057(16) 0.0039(16) -0.0029(15) C12 0.095(2) 0.081(2) 0.076(2) -0.0019(18) 0.0212(18) -0.0014(18) C13 0.086(2) 0.0602(18) 0.079(2) 0.0160(16) 0.0246(17) -0.0011(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.431(3) . ? O1 C10 1.453(3) . ? O2 C7 1.361(3) . ? O2 C8 1.448(3) . ? N1 C1 1.276(3) . ? C1 C2 1.445(4) . ? C1 C9 1.490(3) . ? C2 C3 1.389(4) . ? C2 C7 1.397(4) . ? C3 C4 1.379(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(5) . ? C4 H4 0.9300 . ? C5 C6 1.361(5) . ? C5 H5 0.9300 . ? C6 C7 1.388(4) . ? C6 H6 0.9300 . ? C8 C13 1.505(4) . ? C8 C9 1.505(3) . ? C8 H8 0.9800 . ? C9 C10 1.510(3) . ? C9 H9 0.9800 . ? C10 C11 1.507(4) . ? C10 H10 0.9800 . ? C11 C12 1.515(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.520(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? 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 N1 O1 C10 106.80(18) . . ? C7 O2 C8 118.6(2) . . ? C1 N1 O1 107.4(2) . . ? N1 C1 C2 126.8(3) . . ? N1 C1 C9 113.9(3) . . ? C2 C1 C9 119.3(2) . . ? C3 C2 C7 118.8(3) . . ? C3 C2 C1 124.8(3) . . ? C7 C2 C1 116.4(3) . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 120.1(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? O2 C7 C6 116.2(3) . . ? O2 C7 C2 124.1(3) . . ? C6 C7 C2 119.7(3) . . ? O2 C8 C13 111.5(2) . . ? O2 C8 C9 110.4(2) . . ? C13 C8 C9 112.8(2) . . ? O2 C8 H8 107.3 . . ? C13 C8 H8 107.3 . . ? C9 C8 H8 107.3 . . ? C1 C9 C8 111.6(2) . . ? C1 C9 C10 99.0(2) . . ? C8 C9 C10 118.6(2) . . ? C1 C9 H9 109.0 . . ? C8 C9 H9 109.0 . . ? C10 C9 H9 109.0 . . ? O1 C10 C11 108.9(2) . . ? O1 C10 C9 102.3(2) . . ? C11 C10 C9 114.2(2) . . ? O1 C10 H10 110.4 . . ? C11 C10 H10 110.4 . . ? C9 C10 H10 110.4 . . ? C10 C11 C12 112.6(2) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 109.9(2) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C8 C13 C12 109.7(2) . . ? C8 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C8 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.227 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.065 # Attachment '3.txt' data_a10098 _database_code_depnum_ccdc_archive 'CCDC 757190' #TrackingRef '4.cif' #Author Ching Fa Yao #expected journal for publication OBC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N O5' _chemical_formula_sum 'C11 H13 N O5' _chemical_formula_weight 239.22 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 'P 21 21 21' 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 8.4490(8) _cell_length_b 11.2583(12) _cell_length_c 12.0738(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1148.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9656 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3809 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1957 _reflns_number_gt 1604 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0457P)^2^+0.0167P] 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 fixed _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 -0.8(13) _refine_ls_number_reflns 1957 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1179(3) 0.3397(2) 0.6993(2) 0.0649(6) Uani 1 1 d . . . H1 H 1.1445 0.2665 0.6690 0.078 Uiso 1 1 calc R . . C2 C 1.0966(3) 0.35988(19) 0.80759(18) 0.0551(5) Uani 1 1 d . . . C3 C 1.0987(3) 0.2857(2) 0.9107(2) 0.0707(6) Uani 1 1 d . . . H3A H 1.0601 0.2064 0.8945 0.085 Uiso 1 1 calc R . . H3B H 1.2060 0.2792 0.9386 0.085 Uiso 1 1 calc R . . C4 C 1.0494(2) 0.45866(18) 1.01652(16) 0.0544(5) Uani 1 1 d . . . H4 H 1.1593 0.4608 1.0425 0.065 Uiso 1 1 calc R . . C5 C 1.0222(2) 0.54312(18) 0.91933(16) 0.0506(5) Uani 1 1 d . . . H5 H 1.0870 0.6148 0.9273 0.061 Uiso 1 1 calc R . . C6 C 1.0585(2) 0.48108(18) 0.81231(16) 0.0511(5) Uani 1 1 d . . . C7 C 0.8032(2) 0.56447(18) 1.03480(15) 0.0490(5) Uani 1 1 d . . . H7 H 0.7071 0.5160 1.0394 0.059 Uiso 1 1 calc R . . C8 C 0.9362(2) 0.5085(2) 1.10163(17) 0.0572(6) Uani 1 1 d . . . H8 H 0.8991 0.4490 1.1549 0.069 Uiso 1 1 calc R . . C9 C 0.8963(3) 0.7004(2) 1.16397(16) 0.0572(5) Uani 1 1 d . . . C10 C 0.9746(3) 0.8158(2) 1.1378(2) 0.0832(8) Uani 1 1 d . . . H10A H 1.0543 0.8322 1.1924 0.125 Uiso 1 1 calc R . . H10B H 0.8972 0.8782 1.1383 0.125 Uiso 1 1 calc R . . H10C H 1.0228 0.8113 1.0659 0.125 Uiso 1 1 calc R . . C11 C 0.8218(3) 0.6964(2) 1.2772(2) 0.0800(7) Uani 1 1 d . . . H11A H 0.9008 0.7124 1.3323 0.120 Uiso 1 1 calc R . . H11B H 0.7773 0.6191 1.2897 0.120 Uiso 1 1 calc R . . H11C H 0.7397 0.7552 1.2818 0.120 Uiso 1 1 calc R . . N1 N 1.0567(2) 0.53232(17) 0.71516(15) 0.0662(5) Uani 1 1 d . . . O1 O 1.0954(2) 0.43952(16) 0.64043(12) 0.0714(5) Uani 1 1 d . . . O2 O 0.99936(19) 0.34125(13) 0.99196(12) 0.0622(4) Uani 1 1 d . . . O3 O 0.85705(16) 0.57198(12) 0.92353(11) 0.0543(4) Uani 1 1 d . . . O4 O 0.77782(17) 0.67623(13) 1.08140(12) 0.0675(4) Uani 1 1 d . . . O5 O 1.01016(17) 0.60766(15) 1.15244(12) 0.0696(5) 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 0.0546(14) 0.0568(15) 0.0832(16) -0.0144(12) 0.0050(12) -0.0026(10) C2 0.0433(12) 0.0524(13) 0.0695(13) -0.0106(11) -0.0045(10) 0.0027(9) C3 0.0751(15) 0.0525(14) 0.0845(15) -0.0059(13) -0.0153(13) 0.0154(12) C4 0.0491(13) 0.0549(14) 0.0593(11) -0.0058(10) -0.0157(10) 0.0063(10) C5 0.0450(12) 0.0453(12) 0.0616(11) -0.0032(10) -0.0004(10) -0.0067(9) C6 0.0438(12) 0.0489(12) 0.0607(12) -0.0027(10) 0.0014(9) -0.0050(9) C7 0.0441(11) 0.0516(13) 0.0512(10) -0.0013(9) -0.0037(9) -0.0042(9) C8 0.0584(14) 0.0595(14) 0.0537(11) 0.0024(10) -0.0103(10) 0.0008(11) C9 0.0446(11) 0.0690(15) 0.0579(11) -0.0171(11) -0.0022(10) -0.0011(10) C10 0.0737(16) 0.091(2) 0.0851(16) -0.0125(14) 0.0101(14) -0.0223(15) C11 0.0683(15) 0.105(2) 0.0661(12) -0.0086(14) 0.0084(12) -0.0059(14) N1 0.0761(13) 0.0581(12) 0.0644(10) -0.0005(10) 0.0108(9) -0.0035(10) O1 0.0743(11) 0.0751(12) 0.0647(9) -0.0125(9) 0.0149(8) -0.0099(9) O2 0.0738(10) 0.0459(9) 0.0670(9) 0.0028(7) -0.0107(8) 0.0060(7) O3 0.0522(8) 0.0591(10) 0.0515(7) 0.0043(7) -0.0026(6) 0.0112(6) O4 0.0590(8) 0.0710(11) 0.0726(9) -0.0243(8) -0.0198(8) 0.0127(8) O5 0.0546(9) 0.0874(11) 0.0667(9) -0.0260(8) -0.0175(8) 0.0095(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 C1 C2 1.339(3) . ? C1 O1 1.343(3) . ? C1 H1 0.9300 . ? C2 C6 1.403(3) . ? C2 C3 1.499(3) . ? C3 O2 1.435(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.419(2) . ? C4 C8 1.512(3) . ? C4 C5 1.528(3) . ? C4 H4 0.9800 . ? C5 O3 1.434(3) . ? C5 C6 1.500(3) . ? C5 H5 0.9800 . ? C6 N1 1.307(3) . ? C7 O4 1.395(2) . ? C7 O3 1.421(2) . ? C7 C8 1.520(3) . ? C7 H7 0.9800 . ? C8 O5 1.419(3) . ? C8 H8 0.9800 . ? C9 O5 1.427(3) . ? C9 O4 1.439(2) . ? C9 C10 1.492(3) . ? C9 C11 1.506(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 O1 1.419(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O1 110.9(2) . . ? C2 C1 H1 124.6 . . ? O1 C1 H1 124.6 . . ? C1 C2 C6 103.6(2) . . ? C1 C2 C3 135.6(2) . . ? C6 C2 C3 120.7(2) . . ? O2 C3 C2 108.55(18) . . ? O2 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? O2 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? O2 C4 C8 107.41(18) . . ? O2 C4 C5 111.99(16) . . ? C8 C4 C5 101.30(16) . . ? O2 C4 H4 111.9 . . ? C8 C4 H4 111.9 . . ? C5 C4 H4 111.9 . . ? O3 C5 C6 109.56(16) . . ? O3 C5 C4 105.08(16) . . ? C6 C5 C4 109.94(16) . . ? O3 C5 H5 110.7 . . ? C6 C5 H5 110.7 . . ? C4 C5 H5 110.7 . . ? N1 C6 C2 113.29(19) . . ? N1 C6 C5 124.40(19) . . ? C2 C6 C5 122.3(2) . . ? O4 C7 O3 112.15(16) . . ? O4 C7 C8 105.88(15) . . ? O3 C7 C8 106.86(16) . . ? O4 C7 H7 110.6 . . ? O3 C7 H7 110.6 . . ? C8 C7 H7 110.6 . . ? O5 C8 C4 107.91(17) . . ? O5 C8 C7 103.22(17) . . ? C4 C8 C7 105.11(16) . . ? O5 C8 H8 113.3 . . ? C4 C8 H8 113.3 . . ? C7 C8 H8 113.3 . . ? O5 C9 O4 105.25(15) . . ? O5 C9 C10 108.50(18) . . ? O4 C9 C10 109.07(19) . . ? O5 C9 C11 110.4(2) . . ? O4 C9 C11 109.43(17) . . ? C10 C9 C11 113.81(19) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 N1 O1 104.07(17) . . ? C1 O1 N1 108.17(16) . . ? C4 O2 C3 111.99(17) . . ? C7 O3 C5 109.36(14) . . ? C7 O4 C9 110.06(15) . . ? C8 O5 C9 108.74(15) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.101 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.033