Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Xu, Jian-Hua' 'Fun, Hoong-Kun' 'Gao, Yi' 'Xue, Jie' 'Zhang, Yan' _publ_contact_author_name 'Prof Jian-Hua Xu' _publ_contact_author_address ; Chemistry Nnjing University Nanjing210093, P.R.China Nanjing 210093 CHINA ; _publ_contact_author_email 'XUJH@NJU.EDU.CN' _publ_section_title ; Photoinduced [2+2] Cycloadditions (the Paterno-Büchi Reaction) of 1-Acetylisatin with Enol Ethers ? Regioselectivity, Diastereoselectivity and Acid Catalysed Transformations of the Spirooxetane Products ; data_compound8 _database_code_CSD 173803 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N O4' _chemical_formula_weight 257.24 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 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 19.2158(1) _cell_length_b 9.2422(2) _cell_length_c 15.6965(3) _cell_angle_alpha 90.00 _cell_angle_beta 121.111(1) _cell_angle_gamma 90.00 _cell_volume 2386.69(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3352 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 8222 _diffrn_reflns_av_R_equivalents 0.1385 _diffrn_reflns_av_sigmaI/netI 0.1312 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2893 _reflns_number_gt 1349 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.1078P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0128(19) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2893 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1383 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2124 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _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 0.22503(16) 0.3396(3) 0.38753(17) 0.0738(8) Uani 1 1 d . . . O2 O 0.22868(11) 0.1421(2) 0.29500(13) 0.0520(6) Uani 1 1 d . . . O3 O 0.11606(17) -0.1083(3) 0.23077(17) 0.0834(9) Uani 1 1 d . . . O4 O 0.05513(16) -0.1797(3) -0.06136(19) 0.0741(8) Uani 1 1 d . . . N1 N 0.10048(13) -0.0461(2) 0.07802(16) 0.0397(6) Uani 1 1 d . . . C1 C 0.11670(15) 0.0826(3) 0.04060(19) 0.0361(6) Uani 1 1 d . . . C2 C 0.1068(2) 0.1084(3) -0.0517(2) 0.0550(9) Uani 1 1 d . . . H2A H 0.0858 0.0376 -0.1009 0.066 Uiso 1 1 calc R . . C3 C 0.1291(2) 0.2423(4) -0.0686(3) 0.0709(11) Uani 1 1 d . . . H3A H 0.1236 0.2612 -0.1301 0.085 Uiso 1 1 calc R . . C4 C 0.1594(3) 0.3484(4) 0.0031(3) 0.0728(11) Uani 1 1 d . . . H4A H 0.1730 0.4383 -0.0108 0.087 Uiso 1 1 calc R . . C5 C 0.16964(19) 0.3223(3) 0.0957(2) 0.0507(8) Uani 1 1 d . . . H5A H 0.1922 0.3924 0.1453 0.061 Uiso 1 1 calc R . . C6 C 0.14588(15) 0.1907(3) 0.11300(18) 0.0354(6) Uani 1 1 d . . . C7 C 0.14957(16) 0.1345(3) 0.20401(18) 0.0374(6) Uani 1 1 d . . . C9 C 0.1689(2) 0.4335(4) 0.3175(3) 0.0725(11) Uani 1 1 d . . . H9A H 0.1770 0.5331 0.3221 0.087 Uiso 1 1 calc R . . C10 C 0.1035(2) 0.3735(4) 0.2440(2) 0.0609(9) Uani 1 1 d . . . H10A H 0.0597 0.4224 0.1923 0.073 Uiso 1 1 calc R . . C11 C 0.11135(17) 0.2145(3) 0.2575(2) 0.0451(7) Uani 1 1 d . . . H11A H 0.0666 0.1647 0.2582 0.054 Uiso 1 1 calc R . . C8 C 0.19467(19) 0.1990(4) 0.3502(2) 0.0547(9) Uani 1 1 d . . . H8A H 0.1965 0.1322 0.3998 0.066 Uiso 1 1 calc R . . C12 C 0.12071(17) -0.0220(3) 0.1766(2) 0.0484(8) Uani 1 1 d . . . C13 C 0.07453(17) -0.1778(3) 0.0249(2) 0.0480(8) Uani 1 1 d . . . C14 C 0.0698(2) -0.3078(3) 0.0780(3) 0.0708(11) Uani 1 1 d . . . H14A H 0.0880 -0.2830 0.1458 0.106 Uiso 1 1 calc R . . H14B H 0.1038 -0.3830 0.0768 0.106 Uiso 1 1 calc R . . H14C H 0.0146 -0.3413 0.0457 0.106 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 0.0862(18) 0.0794(19) 0.0533(14) -0.0274(13) 0.0343(13) -0.0201(13) O2 0.0487(13) 0.0570(13) 0.0408(11) -0.0018(9) 0.0165(10) 0.0011(9) O3 0.135(2) 0.0545(15) 0.0526(14) 0.0135(11) 0.0431(16) -0.0247(14) O4 0.0984(19) 0.0540(15) 0.0637(16) -0.0247(12) 0.0375(14) -0.0197(11) N1 0.0471(14) 0.0316(12) 0.0380(12) -0.0012(9) 0.0203(11) 0.0000(9) C1 0.0420(15) 0.0342(14) 0.0413(14) -0.0020(11) 0.0282(13) 0.0010(11) C2 0.086(2) 0.0477(19) 0.0492(18) -0.0129(14) 0.0475(17) -0.0089(15) C3 0.121(3) 0.062(2) 0.061(2) -0.0102(17) 0.070(2) -0.025(2) C4 0.134(3) 0.047(2) 0.070(2) -0.0076(16) 0.076(2) -0.0297(19) C5 0.077(2) 0.0382(16) 0.0535(17) -0.0086(13) 0.0457(17) -0.0129(13) C6 0.0416(15) 0.0344(14) 0.0387(14) -0.0011(11) 0.0267(12) -0.0024(10) C7 0.0417(15) 0.0371(14) 0.0303(13) -0.0004(11) 0.0164(12) -0.0020(11) C9 0.117(3) 0.054(2) 0.075(3) -0.0142(19) 0.070(3) -0.003(2) C10 0.083(3) 0.061(2) 0.0523(19) -0.0052(16) 0.044(2) 0.0134(17) C11 0.0525(18) 0.0525(18) 0.0387(15) -0.0047(13) 0.0296(14) -0.0075(13) C8 0.069(2) 0.060(2) 0.0347(15) -0.0020(14) 0.0272(16) -0.0090(15) C12 0.0583(19) 0.0389(16) 0.0410(16) 0.0062(13) 0.0208(14) -0.0036(12) C13 0.0415(17) 0.0386(16) 0.0551(19) -0.0071(13) 0.0189(14) -0.0016(11) C14 0.074(2) 0.0339(17) 0.080(3) 0.0022(16) 0.022(2) -0.0011(14) _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 C9 1.378(4) . ? O1 C8 1.421(4) . ? O2 C8 1.428(3) . ? O2 C7 1.453(3) . ? O3 C12 1.202(3) . ? O4 C13 1.205(4) . ? N1 C12 1.405(4) . ? N1 C13 1.412(3) . ? N1 C1 1.430(3) . ? C1 C2 1.381(4) . ? C1 C6 1.395(4) . ? C2 C3 1.379(4) . ? C2 H2A 0.9300 . ? C3 C4 1.375(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 H4A 0.9300 . ? C5 C6 1.375(4) . ? C5 H5A 0.9300 . ? C6 C7 1.487(3) . ? C7 C12 1.529(4) . ? C7 C11 1.559(4) . ? C9 C10 1.312(5) . ? C9 H9A 0.9300 . ? C10 C11 1.481(4) . ? C10 H10A 0.9300 . ? C11 C8 1.514(4) . ? C11 H11A 0.9800 . ? C8 H8A 0.9800 . ? C13 C14 1.492(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C8 105.2(3) . . ? C8 O2 C7 92.29(19) . . ? C12 N1 C13 126.8(2) . . ? C12 N1 C1 109.0(2) . . ? C13 N1 C1 124.0(2) . . ? C2 C1 C6 120.7(2) . . ? C2 C1 N1 129.3(2) . . ? C6 C1 N1 110.0(2) . . ? C3 C2 C1 118.0(3) . . ? C3 C2 H2A 121.0 . . ? C1 C2 H2A 121.0 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 118.7(3) . . ? C6 C5 H5A 120.7 . . ? C4 C5 H5A 120.7 . . ? C5 C6 C1 120.5(2) . . ? C5 C6 C7 130.0(2) . . ? C1 C6 C7 109.4(2) . . ? O2 C7 C6 115.7(2) . . ? O2 C7 C12 111.5(2) . . ? C6 C7 C12 103.3(2) . . ? O2 C7 C11 89.55(19) . . ? C6 C7 C11 123.4(2) . . ? C12 C7 C11 113.4(2) . . ? C10 C9 O1 115.8(3) . . ? C10 C9 H9A 122.1 . . ? O1 C9 H9A 122.1 . . ? C9 C10 C11 108.2(3) . . ? C9 C10 H10A 125.9 . . ? C11 C10 H10A 125.9 . . ? C10 C11 C8 102.1(2) . . ? C10 C11 C7 115.8(2) . . ? C8 C11 C7 85.1(2) . . ? C10 C11 H11A 116.3 . . ? C8 C11 H11A 116.3 . . ? C7 C11 H11A 116.3 . . ? O1 C8 O2 111.6(3) . . ? O1 C8 C11 108.3(3) . . ? O2 C8 C11 92.3(2) . . ? O1 C8 H8A 114.2 . . ? O2 C8 H8A 114.2 . . ? C11 C8 H8A 114.2 . . ? O3 C12 N1 126.5(3) . . ? O3 C12 C7 125.3(3) . . ? N1 C12 C7 108.3(2) . . ? O4 C13 N1 119.1(3) . . ? O4 C13 C14 122.9(3) . . ? N1 C13 C14 118.0(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C12 N1 C1 C2 179.4(3) . . . . ? C13 N1 C1 C2 4.0(4) . . . . ? C12 N1 C1 C6 -1.0(3) . . . . ? C13 N1 C1 C6 -176.4(2) . . . . ? C6 C1 C2 C3 2.0(5) . . . . ? N1 C1 C2 C3 -178.4(3) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C2 C3 C4 C5 1.1(6) . . . . ? C3 C4 C5 C6 -2.7(6) . . . . ? C4 C5 C6 C1 3.9(5) . . . . ? C4 C5 C6 C7 -179.8(3) . . . . ? C2 C1 C6 C5 -3.7(4) . . . . ? N1 C1 C6 C5 176.7(2) . . . . ? C2 C1 C6 C7 179.4(2) . . . . ? N1 C1 C6 C7 -0.3(3) . . . . ? C8 O2 C7 C6 134.2(2) . . . . ? C8 O2 C7 C12 -108.2(2) . . . . ? C8 O2 C7 C11 6.8(2) . . . . ? C5 C6 C7 O2 -53.2(4) . . . . ? C1 C6 C7 O2 123.4(2) . . . . ? C5 C6 C7 C12 -175.3(3) . . . . ? C1 C6 C7 C12 1.3(3) . . . . ? C5 C6 C7 C11 54.6(4) . . . . ? C1 C6 C7 C11 -128.8(3) . . . . ? C8 O1 C9 C10 5.0(4) . . . . ? O1 C9 C10 C11 -1.9(4) . . . . ? C9 C10 C11 C8 -1.9(3) . . . . ? C9 C10 C11 C7 -92.3(3) . . . . ? O2 C7 C11 C10 94.7(3) . . . . ? C6 C7 C11 C10 -26.3(4) . . . . ? C12 C7 C11 C10 -152.1(3) . . . . ? O2 C7 C11 C8 -6.4(2) . . . . ? C6 C7 C11 C8 -127.4(3) . . . . ? C12 C7 C11 C8 106.8(2) . . . . ? C9 O1 C8 O2 94.3(3) . . . . ? C9 O1 C8 C11 -5.9(3) . . . . ? C7 O2 C8 O1 -117.8(3) . . . . ? C7 O2 C8 C11 -7.0(2) . . . . ? C10 C11 C8 O1 4.9(3) . . . . ? C7 C11 C8 O1 120.2(2) . . . . ? C10 C11 C8 O2 -108.8(2) . . . . ? C7 C11 C8 O2 6.6(2) . . . . ? C13 N1 C12 O3 -3.3(5) . . . . ? C1 N1 C12 O3 -178.5(3) . . . . ? C13 N1 C12 C7 177.0(2) . . . . ? C1 N1 C12 C7 1.8(3) . . . . ? O2 C7 C12 O3 53.5(4) . . . . ? C6 C7 C12 O3 178.4(3) . . . . ? C11 C7 C12 O3 -45.7(4) . . . . ? O2 C7 C12 N1 -126.8(2) . . . . ? C6 C7 C12 N1 -1.9(3) . . . . ? C11 C7 C12 N1 134.0(2) . . . . ? C12 N1 C13 O4 176.1(3) . . . . ? C1 N1 C13 O4 -9.4(4) . . . . ? C12 N1 C13 C14 -1.9(4) . . . . ? C1 N1 C13 C14 172.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.532 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.116 #cif file of compound 23 data_compound23 _database_code_CSD 175732 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 N O4' _chemical_formula_weight 297.30 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.9269(6) _cell_length_b 10.8140(2) _cell_length_c 8.8675(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.985(1) _cell_angle_gamma 90.00 _cell_volume 1493.99(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 28.36 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 10295 _diffrn_reflns_av_R_equivalents 0.1227 _diffrn_reflns_av_sigmaI/netI 0.1555 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3646 _reflns_number_gt 1378 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.0666P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.045(4) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3646 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1693 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1716 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _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 0.42403(12) 0.37707(16) 0.46866(19) 0.0582(6) Uani 1 1 d . . . O2 O 0.35482(13) 0.24823(16) 0.1759(2) 0.0637(6) Uani 1 1 d . . . H2B H 0.4045 0.2407 0.1651 0.096 Uiso 1 1 calc R . . O3 O 0.11720(13) 0.40965(19) 0.0777(2) 0.0778(7) Uani 1 1 d . . . O4 O 0.14241(13) 0.22167(18) 0.2057(2) 0.0703(6) Uani 1 1 d . . . N1 N 0.44754(14) 0.51760(19) 0.2888(2) 0.0497(6) Uani 1 1 d . . . H1A H 0.4881 0.5588 0.3463 0.060 Uiso 1 1 calc R . . C1 C 0.34851(16) 0.4614(2) 0.0744(3) 0.0430(7) Uani 1 1 d . . . C2 C 0.30750(19) 0.4685(2) -0.0782(3) 0.0572(8) Uani 1 1 d . . . H2A H 0.2630 0.4146 -0.1187 0.069 Uiso 1 1 calc R . . C3 C 0.3343(2) 0.5586(3) -0.1709(3) 0.0684(9) Uani 1 1 d . . . H3A H 0.3080 0.5638 -0.2747 0.082 Uiso 1 1 calc R . . C4 C 0.3989(2) 0.6397(3) -0.1105(4) 0.0664(9) Uani 1 1 d . . . H4A H 0.4146 0.7002 -0.1738 0.080 Uiso 1 1 calc R . . C5 C 0.44119(19) 0.6333(2) 0.0424(3) 0.0580(8) Uani 1 1 d . . . H5A H 0.4857 0.6872 0.0829 0.070 Uiso 1 1 calc R . . C6 C 0.41455(17) 0.5442(2) 0.1310(3) 0.0449(7) Uani 1 1 d . . . C7 C 0.40828(16) 0.4215(2) 0.3375(3) 0.0456(7) Uani 1 1 d . . . C8 C 0.33796(17) 0.3746(2) 0.2021(3) 0.0443(7) Uani 1 1 d . . . C9 C 0.25067(17) 0.3762(2) 0.2523(3) 0.0473(7) Uani 1 1 d . . . H9A H 0.2571 0.3305 0.3494 0.057 Uiso 1 1 calc R . . C10 C 0.21437(17) 0.5005(2) 0.2744(3) 0.0487(7) Uani 1 1 d . . . C11 C 0.2417(2) 0.5954(3) 0.3760(3) 0.0669(9) Uani 1 1 d . . . H11A H 0.2937 0.5898 0.4464 0.080 Uiso 1 1 calc R . . C12 C 0.1904(3) 0.6995(3) 0.3718(4) 0.0844(11) Uani 1 1 d . . . H12A H 0.2082 0.7640 0.4404 0.101 Uiso 1 1 calc R . . C13 C 0.1134(3) 0.7086(3) 0.2673(5) 0.0952(12) Uani 1 1 d . . . H13A H 0.0801 0.7794 0.2653 0.114 Uiso 1 1 calc R . . C14 C 0.0857(2) 0.6140(3) 0.1661(5) 0.0885(12) Uani 1 1 d . . . H14A H 0.0337 0.6191 0.0956 0.106 Uiso 1 1 calc R . . C15 C 0.1370(2) 0.5117(3) 0.1722(3) 0.0622(8) Uani 1 1 d . . . C16 C 0.17840(18) 0.3152(3) 0.1335(3) 0.0578(8) Uani 1 1 d . . . H16A H 0.2016 0.2812 0.0482 0.069 Uiso 1 1 calc R . . C17 C 0.0903(2) 0.1370(3) 0.1013(5) 0.0951(12) Uani 1 1 d . . . H17A H 0.0676 0.0749 0.1591 0.143 Uiso 1 1 calc R . . H17B H 0.1247 0.0983 0.0377 0.143 Uiso 1 1 calc R . . H17C H 0.0439 0.1812 0.0375 0.143 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 0.0581(13) 0.0744(13) 0.0389(11) 0.0097(9) 0.0022(9) -0.0035(9) O2 0.0802(16) 0.0479(12) 0.0681(13) 0.0019(9) 0.0272(11) 0.0049(10) O3 0.0643(15) 0.0740(15) 0.0802(15) 0.0005(12) -0.0197(12) 0.0016(11) O4 0.0641(15) 0.0680(14) 0.0790(15) 0.0041(11) 0.0149(12) -0.0175(11) N1 0.0458(15) 0.0588(15) 0.0419(13) -0.0011(10) 0.0029(10) -0.0053(11) C1 0.0454(17) 0.0488(16) 0.0351(14) -0.0020(12) 0.0093(12) 0.0026(12) C2 0.067(2) 0.0583(18) 0.0447(16) -0.0009(14) 0.0087(15) -0.0053(15) C3 0.096(3) 0.074(2) 0.0348(16) 0.0065(15) 0.0127(16) 0.0015(18) C4 0.088(3) 0.0586(19) 0.059(2) 0.0081(15) 0.0293(18) -0.0034(17) C5 0.066(2) 0.0562(18) 0.0554(19) -0.0014(14) 0.0206(15) -0.0072(14) C6 0.0476(18) 0.0531(17) 0.0355(15) -0.0004(12) 0.0118(13) 0.0038(13) C7 0.0404(17) 0.0524(17) 0.0437(16) 0.0001(14) 0.0079(13) 0.0030(13) C8 0.0491(17) 0.0423(16) 0.0405(15) 0.0004(11) 0.0070(12) -0.0011(12) C9 0.0446(17) 0.0599(18) 0.0360(14) 0.0035(12) 0.0050(12) -0.0044(13) C10 0.0433(17) 0.0595(19) 0.0450(16) 0.0004(14) 0.0133(13) -0.0004(13) C11 0.061(2) 0.080(2) 0.063(2) -0.0161(17) 0.0215(16) 0.0003(18) C12 0.081(3) 0.079(3) 0.103(3) -0.026(2) 0.043(2) -0.006(2) C13 0.078(3) 0.073(3) 0.139(4) 0.004(2) 0.033(3) 0.016(2) C14 0.066(3) 0.077(3) 0.114(3) 0.012(2) 0.000(2) 0.011(2) C15 0.057(2) 0.059(2) 0.068(2) 0.0062(16) 0.0081(17) -0.0003(16) C16 0.053(2) 0.0611(19) 0.0574(18) 0.0026(15) 0.0066(15) -0.0024(15) C17 0.077(3) 0.080(2) 0.126(3) -0.017(2) 0.016(2) -0.0317(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 C7 1.235(3) . ? O2 C8 1.421(3) . ? O2 H2B 0.8200 . ? O3 C15 1.382(3) . ? O3 C16 1.427(3) . ? O4 C16 1.383(3) . ? O4 C17 1.436(3) . ? N1 C7 1.330(3) . ? N1 C6 1.419(3) . ? N1 H1A 0.8600 . ? C1 C2 1.377(3) . ? C1 C6 1.393(3) . ? C1 C8 1.507(3) . ? C2 C3 1.397(4) . ? C2 H2A 0.9300 . ? C3 C4 1.373(4) . ? C3 H3A 0.9300 . ? C4 C5 1.385(4) . ? C4 H4A 0.9300 . ? C5 C6 1.365(3) . ? C5 H5A 0.9300 . ? C7 C8 1.547(3) . ? C8 C9 1.545(4) . ? C9 C10 1.492(3) . ? C9 C16 1.538(3) . ? C9 H9A 0.9800 . ? C10 C15 1.375(4) . ? C10 C11 1.375(4) . ? C11 C12 1.386(4) . ? C11 H11A 0.9300 . ? C12 C13 1.379(5) . ? C12 H12A 0.9300 . ? C13 C14 1.372(5) . ? C13 H13A 0.9300 . ? C14 C15 1.369(4) . ? C14 H14A 0.9300 . ? C16 H16A 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 H2B 109.5 . . ? C15 O3 C16 107.9(2) . . ? C16 O4 C17 114.1(2) . . ? C7 N1 C6 112.1(2) . . ? C7 N1 H1A 124.0 . . ? C6 N1 H1A 124.0 . . ? C2 C1 C6 119.1(2) . . ? C2 C1 C8 132.0(2) . . ? C6 C1 C8 108.9(2) . . ? C1 C2 C3 118.5(3) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 121.5(3) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C6 C5 C4 116.9(3) . . ? C6 C5 H5A 121.5 . . ? C4 C5 H5A 121.5 . . ? C5 C6 C1 123.2(2) . . ? C5 C6 N1 128.0(2) . . ? C1 C6 N1 108.8(2) . . ? O1 C7 N1 126.3(2) . . ? O1 C7 C8 125.2(2) . . ? N1 C7 C8 108.5(2) . . ? O2 C8 C1 115.0(2) . . ? O2 C8 C9 105.65(19) . . ? C1 C8 C9 117.2(2) . . ? O2 C8 C7 108.1(2) . . ? C1 C8 C7 101.7(2) . . ? C9 C8 C7 108.8(2) . . ? C10 C9 C16 102.8(2) . . ? C10 C9 C8 116.4(2) . . ? C16 C9 C8 112.8(2) . . ? C10 C9 H9A 108.2 . . ? C16 C9 H9A 108.2 . . ? C8 C9 H9A 108.2 . . ? C15 C10 C11 118.9(3) . . ? C15 C10 C9 108.2(2) . . ? C11 C10 C9 132.8(3) . . ? C10 C11 C12 119.0(3) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C15 C14 C13 117.9(3) . . ? C15 C14 H14A 121.1 . . ? C13 C14 H14A 121.1 . . ? C14 C15 C10 122.9(3) . . ? C14 C15 O3 124.2(3) . . ? C10 C15 O3 112.9(2) . . ? O4 C16 O3 111.4(2) . . ? O4 C16 C9 108.7(2) . . ? O3 C16 C9 106.9(2) . . ? O4 C16 H16A 109.9 . . ? O3 C16 H16A 109.9 . . ? C9 C16 H16A 109.9 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C6 C1 C2 C3 0.3(4) . . . . ? C8 C1 C2 C3 -177.7(3) . . . . ? C1 C2 C3 C4 -1.2(4) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? C4 C5 C6 C1 0.3(4) . . . . ? C4 C5 C6 N1 179.2(3) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C8 C1 C6 C5 178.5(2) . . . . ? C2 C1 C6 N1 -179.0(2) . . . . ? C8 C1 C6 N1 -0.5(3) . . . . ? C7 N1 C6 C5 -177.8(3) . . . . ? C7 N1 C6 C1 1.2(3) . . . . ? C6 N1 C7 O1 179.4(2) . . . . ? C6 N1 C7 C8 -1.3(3) . . . . ? C2 C1 C8 O2 61.5(4) . . . . ? C6 C1 C8 O2 -116.8(2) . . . . ? C2 C1 C8 C9 -63.5(4) . . . . ? C6 C1 C8 C9 118.2(2) . . . . ? C2 C1 C8 C7 178.0(3) . . . . ? C6 C1 C8 C7 -0.2(3) . . . . ? O1 C7 C8 O2 -58.4(3) . . . . ? N1 C7 C8 O2 122.4(2) . . . . ? O1 C7 C8 C1 -179.8(2) . . . . ? N1 C7 C8 C1 0.9(3) . . . . ? O1 C7 C8 C9 55.9(3) . . . . ? N1 C7 C8 C9 -123.4(2) . . . . ? O2 C8 C9 C10 -175.0(2) . . . . ? C1 C8 C9 C10 -45.5(3) . . . . ? C7 C8 C9 C10 69.1(3) . . . . ? O2 C8 C9 C16 -56.6(3) . . . . ? C1 C8 C9 C16 73.0(3) . . . . ? C7 C8 C9 C16 -172.4(2) . . . . ? C16 C9 C10 C15 -5.1(3) . . . . ? C8 C9 C10 C15 118.7(3) . . . . ? C16 C9 C10 C11 172.0(3) . . . . ? C8 C9 C10 C11 -64.2(4) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C9 C10 C11 C12 -177.0(3) . . . . ? C10 C11 C12 C13 -0.3(5) . . . . ? C11 C12 C13 C14 0.6(6) . . . . ? C12 C13 C14 C15 -0.4(6) . . . . ? C13 C14 C15 C10 -0.1(5) . . . . ? C13 C14 C15 O3 179.9(3) . . . . ? C11 C10 C15 C14 0.4(5) . . . . ? C9 C10 C15 C14 178.0(3) . . . . ? C11 C10 C15 O3 -179.6(2) . . . . ? C9 C10 C15 O3 -2.1(3) . . . . ? C16 O3 C15 C14 -171.0(3) . . . . ? C16 O3 C15 C10 9.0(3) . . . . ? C17 O4 C16 O3 77.9(3) . . . . ? C17 O4 C16 C9 -164.5(2) . . . . ? C15 O3 C16 O4 106.8(3) . . . . ? C15 O3 C16 C9 -11.8(3) . . . . ? C10 C9 C16 O4 -110.1(2) . . . . ? C8 C9 C16 O4 123.7(2) . . . . ? C10 C9 C16 O3 10.2(3) . . . . ? C8 C9 C16 O3 -115.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.319 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.086 #Cif file of compound 10 data_compound10 _database_code_CSD 175733 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N2 O7' _chemical_formula_weight 446.40 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0926(4) _cell_length_b 9.1306(4) _cell_length_c 12.1838(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.030(1) _cell_angle_gamma 90.00 _cell_volume 1001.59(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4626 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 28.30 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 7113 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.1429 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4463 _reflns_number_gt 2788 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.0923P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.049(7) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4.4(18) _refine_ls_number_reflns 4463 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.2037 _refine_ls_wR_factor_gt 0.1623 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.0579(3) 0.4073(4) -0.0008(2) 0.0410(8) Uani 1 1 d . . . O2 O 0.2909(3) 0.4431(4) 0.2035(2) 0.0485(9) Uani 1 1 d . . . O3 O 0.1623(3) 0.3823(4) 0.3531(2) 0.0418(8) Uani 1 1 d . . . O4 O -0.3401(5) 0.1633(5) 0.5084(4) 0.0832(14) Uani 1 1 d . . . O5 O -0.1327(4) 0.5123(4) 0.3794(3) 0.0581(10) Uani 1 1 d . . . O6 O 0.2538(4) 0.2011(4) -0.1043(3) 0.0584(10) Uani 1 1 d . . . O7 O 0.5446(4) 0.4655(5) -0.2517(3) 0.0668(11) Uani 1 1 d . . . N1 N -0.1854(3) 0.2632(4) 0.4008(3) 0.0317(7) Uani 1 1 d . . . N2 N 0.3628(3) 0.4222(4) -0.1477(3) 0.0320(7) Uani 1 1 d . . . C1 C 0.0046(5) 0.1649(5) 0.3171(3) 0.0346(9) Uani 1 1 d . . . C2 C 0.0928(6) 0.0532(6) 0.2839(4) 0.0520(13) Uani 1 1 d . . . H2A H 0.1730 0.0745 0.2469 0.062 Uiso 1 1 calc R . . C3 C 0.0596(7) -0.0872(6) 0.3067(4) 0.0589(14) Uani 1 1 d . . . H3A H 0.1182 -0.1627 0.2855 0.071 Uiso 1 1 calc R . . C4 C -0.0587(7) -0.1196(5) 0.3604(4) 0.0564(14) Uani 1 1 d . . . H4A H -0.0798 -0.2174 0.3728 0.068 Uiso 1 1 calc R . . C5 C -0.1482(5) -0.0131(5) 0.3970(4) 0.0423(11) Uani 1 1 d . . . H5A H -0.2271 -0.0362 0.4348 0.051 Uiso 1 1 calc R . . C6 C -0.1130(5) 0.1311(4) 0.3738(3) 0.0325(9) Uani 1 1 d . . . C7 C -0.1062(5) 0.3832(4) 0.3672(3) 0.0318(9) Uani 1 1 d . . . C8 C 0.0175(4) 0.3244(5) 0.3061(3) 0.0311(8) Uani 1 1 d . . . C9 C 0.0263(4) 0.4103(4) 0.1964(3) 0.0319(8) Uani 1 1 d . . . H9A H -0.0547 0.4796 0.1743 0.038 Uiso 1 1 calc R . . C10 C 0.1701(5) 0.4770(5) 0.2606(4) 0.0386(10) Uani 1 1 d . . . H10A H 0.1618 0.5813 0.2778 0.046 Uiso 1 1 calc R . . C11 C 0.2468(4) 0.3437(5) 0.1146(3) 0.0365(10) Uani 1 1 d . . . H11A H 0.3048 0.2530 0.1163 0.044 Uiso 1 1 calc R . . C12 C 0.0778(4) 0.3233(5) 0.1031(3) 0.0317(8) Uani 1 1 d . . . H12A H 0.0433 0.2216 0.0968 0.038 Uiso 1 1 calc R . . C13 C 0.2161(4) 0.4223(5) -0.0019(3) 0.0323(9) Uani 1 1 d . . . C14 C 0.2678(4) 0.5737(5) -0.0218(3) 0.0332(9) Uani 1 1 d . . . C15 C 0.2397(5) 0.7030(5) 0.0282(4) 0.0406(10) Uani 1 1 d . . . H15A H 0.1866 0.7044 0.0882 0.049 Uiso 1 1 calc R . . C16 C 0.2918(5) 0.8312(6) -0.0123(5) 0.0533(12) Uani 1 1 d . . . H16A H 0.2733 0.9202 0.0203 0.064 Uiso 1 1 calc R . . C17 C 0.3717(5) 0.8281(6) -0.1012(4) 0.0507(12) Uani 1 1 d . . . H17A H 0.4046 0.9155 -0.1284 0.061 Uiso 1 1 calc R . . C18 C 0.4039(5) 0.6952(6) -0.1512(4) 0.0441(11) Uani 1 1 d . . . H18A H 0.4598 0.6927 -0.2095 0.053 Uiso 1 1 calc R . . C19 C 0.3504(4) 0.5715(5) -0.1109(3) 0.0307(9) Uani 1 1 d . . . C20 C 0.2749(5) 0.3301(5) -0.0918(4) 0.0377(9) Uani 1 1 d . . . C21 C 0.4605(5) 0.3775(5) -0.2237(4) 0.0404(10) Uani 1 1 d . . . C22 C 0.4491(6) 0.2274(6) -0.2650(4) 0.0543(13) Uani 1 1 d . . . H22A H 0.3746 0.1760 -0.2315 0.081 Uiso 1 1 calc R . . H22B H 0.5430 0.1790 -0.2466 0.081 Uiso 1 1 calc R . . H22C H 0.4220 0.2284 -0.3440 0.081 Uiso 1 1 calc R . . C23 C -0.3077(5) 0.2715(6) 0.4610(4) 0.0452(11) Uani 1 1 d . . . C24 C -0.3901(7) 0.4033(8) 0.4631(6) 0.081(2) Uani 1 1 d . . . H24A H -0.3478 0.4770 0.4209 0.122 Uiso 1 1 calc R . . H24B H -0.3867 0.4358 0.5384 0.122 Uiso 1 1 calc R . . H24C H -0.4914 0.3861 0.4316 0.122 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(13) 0.064(2) 0.0347(14) 0.0070(15) 0.0074(11) -0.0093(14) O2 0.0276(14) 0.080(3) 0.0395(16) 0.0055(17) 0.0097(12) -0.0149(16) O3 0.0411(16) 0.0532(19) 0.0327(14) 0.0037(13) 0.0103(12) -0.0062(14) O4 0.082(3) 0.077(3) 0.105(3) 0.023(3) 0.067(3) 0.004(2) O5 0.071(3) 0.042(2) 0.070(3) -0.0002(17) 0.039(2) 0.0075(18) O6 0.076(3) 0.042(2) 0.064(2) -0.0042(17) 0.0341(19) -0.0168(17) O7 0.067(2) 0.064(3) 0.080(3) -0.005(2) 0.050(2) -0.016(2) N1 0.0363(17) 0.0265(17) 0.0352(18) 0.0002(15) 0.0157(13) 0.0011(15) N2 0.0326(17) 0.0305(19) 0.0358(17) 0.0002(15) 0.0146(13) -0.0046(15) C1 0.037(2) 0.034(2) 0.034(2) 0.0032(17) 0.0103(16) 0.0075(18) C2 0.068(3) 0.044(3) 0.049(3) 0.003(2) 0.027(2) 0.017(2) C3 0.090(4) 0.035(3) 0.054(3) 0.000(2) 0.020(3) 0.020(3) C4 0.085(4) 0.024(2) 0.058(3) 0.003(2) 0.001(3) 0.002(2) C5 0.054(3) 0.035(2) 0.038(2) 0.0034(19) 0.006(2) -0.007(2) C6 0.038(2) 0.033(2) 0.0268(19) 0.0031(16) 0.0042(16) -0.0064(18) C7 0.040(2) 0.0220(19) 0.035(2) 0.0016(16) 0.0119(17) 0.0028(16) C8 0.0308(19) 0.031(2) 0.033(2) 0.0061(17) 0.0122(15) 0.0032(17) C9 0.0299(19) 0.031(2) 0.037(2) 0.0035(17) 0.0137(15) -0.0003(16) C10 0.041(2) 0.038(2) 0.039(2) 0.0003(18) 0.0128(18) -0.0056(19) C11 0.030(2) 0.043(3) 0.038(2) 0.0037(19) 0.0105(16) -0.0002(18) C12 0.0313(18) 0.036(2) 0.0294(18) 0.0031(16) 0.0085(14) -0.0074(17) C13 0.0256(18) 0.033(2) 0.041(2) 0.0036(18) 0.0120(15) -0.0020(16) C14 0.030(2) 0.035(2) 0.035(2) 0.0052(18) 0.0036(16) 0.0027(17) C15 0.038(2) 0.043(3) 0.041(2) 0.000(2) 0.0068(17) 0.0068(19) C16 0.047(3) 0.041(3) 0.069(3) -0.010(3) -0.002(2) 0.006(2) C17 0.045(3) 0.039(3) 0.067(3) 0.012(3) 0.005(2) -0.003(2) C18 0.027(2) 0.049(3) 0.056(3) 0.009(2) 0.0066(18) -0.0091(19) C19 0.0240(18) 0.032(2) 0.036(2) 0.0037(17) 0.0023(15) -0.0033(16) C20 0.042(2) 0.033(2) 0.041(2) 0.0032(19) 0.0163(18) -0.0086(19) C21 0.037(2) 0.048(3) 0.040(2) -0.0014(19) 0.0180(17) -0.0039(19) C22 0.056(3) 0.058(4) 0.054(3) 0.002(2) 0.025(2) 0.010(2) C23 0.042(2) 0.054(3) 0.045(3) 0.008(2) 0.0251(19) 0.004(2) C24 0.073(4) 0.099(5) 0.084(4) 0.026(4) 0.054(3) 0.028(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.447(4) . ? O1 C12 1.469(5) . ? O2 C10 1.414(5) . ? O2 C11 1.427(5) . ? O3 C10 1.430(5) . ? O3 C8 1.460(5) . ? O4 C23 1.201(6) . ? O5 C7 1.216(5) . ? O6 C20 1.199(5) . ? O7 C21 1.191(5) . ? N1 C7 1.402(5) . ? N1 C23 1.418(5) . ? N1 C6 1.434(5) . ? N2 C20 1.400(5) . ? N2 C21 1.429(5) . ? N2 C19 1.444(5) . ? C1 C6 1.386(6) . ? C1 C2 1.392(6) . ? C1 C8 1.469(6) . ? C2 C3 1.355(8) . ? C2 H2A 0.9300 . ? C3 C4 1.367(8) . ? C3 H3A 0.9300 . ? C4 C5 1.382(7) . ? C4 H4A 0.9300 . ? C5 C6 1.393(6) . ? C5 H5A 0.9300 . ? C7 C8 1.530(6) . ? C8 C9 1.561(5) . ? C9 C12 1.513(6) . ? C9 C10 1.551(6) . ? C9 H9A 0.9800 . ? C10 H10A 0.9800 . ? C11 C12 1.534(5) . ? C11 C13 1.580(6) . ? C11 H11A 0.9800 . ? C12 H12A 0.9800 . ? C13 C14 1.490(6) . ? C13 C20 1.536(6) . ? C14 C15 1.369(6) . ? C14 C19 1.404(6) . ? C15 C16 1.380(7) . ? C15 H15A 0.9300 . ? C16 C17 1.387(7) . ? C16 H16A 0.9300 . ? C17 C18 1.406(7) . ? C17 H17A 0.9300 . ? C18 C19 1.350(6) . ? C18 H18A 0.9300 . ? C21 C22 1.459(7) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.419(8) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 C12 93.1(3) . . ? C10 O2 C11 110.9(3) . . ? C10 O3 C8 92.9(3) . . ? C7 N1 C23 125.5(4) . . ? C7 N1 C6 108.6(3) . . ? C23 N1 C6 125.6(4) . . ? C20 N2 C21 126.3(4) . . ? C20 N2 C19 110.0(3) . . ? C21 N2 C19 123.6(3) . . ? C6 C1 C2 119.8(4) . . ? C6 C1 C8 110.1(4) . . ? C2 C1 C8 130.0(4) . . ? C3 C2 C1 118.7(5) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C3 C4 C5 122.7(5) . . ? C3 C4 H4A 118.7 . . ? C5 C4 H4A 118.7 . . ? C4 C5 C6 115.9(4) . . ? C4 C5 H5A 122.0 . . ? C6 C5 H5A 122.0 . . ? C1 C6 C5 121.8(4) . . ? C1 C6 N1 109.7(3) . . ? C5 C6 N1 128.5(4) . . ? O5 C7 N1 127.1(4) . . ? O5 C7 C8 124.8(4) . . ? N1 C7 C8 108.1(3) . . ? O3 C8 C1 113.7(3) . . ? O3 C8 C7 111.5(3) . . ? C1 C8 C7 103.3(3) . . ? O3 C8 C9 90.1(3) . . ? C1 C8 C9 126.2(4) . . ? C7 C8 C9 111.7(3) . . ? C12 C9 C10 104.9(3) . . ? C12 C9 C8 116.0(3) . . ? C10 C9 C8 84.6(3) . . ? C12 C9 H9A 115.6 . . ? C10 C9 H9A 115.6 . . ? C8 C9 H9A 115.6 . . ? O2 C10 O3 112.5(4) . . ? O2 C10 C9 108.9(3) . . ? O3 C10 C9 91.7(3) . . ? O2 C10 H10A 113.9 . . ? O3 C10 H10A 113.9 . . ? C9 C10 H10A 113.9 . . ? O2 C11 C12 108.5(3) . . ? O2 C11 C13 112.8(4) . . ? C12 C11 C13 85.6(3) . . ? O2 C11 H11A 115.4 . . ? C12 C11 H11A 115.4 . . ? C13 C11 H11A 115.4 . . ? O1 C12 C9 111.1(3) . . ? O1 C12 C11 91.0(3) . . ? C9 C12 C11 106.2(3) . . ? O1 C12 H12A 115.3 . . ? C9 C12 H12A 115.3 . . ? C11 C12 H12A 115.3 . . ? O1 C13 C14 115.2(3) . . ? O1 C13 C20 113.6(3) . . ? C14 C13 C20 104.1(3) . . ? O1 C13 C11 90.0(3) . . ? C14 C13 C11 123.2(3) . . ? C20 C13 C11 110.9(3) . . ? C15 C14 C19 120.6(4) . . ? C15 C14 C13 130.2(4) . . ? C19 C14 C13 109.1(4) . . ? C14 C15 C16 118.6(4) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? C15 C16 C17 120.3(5) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C16 C17 C18 121.3(5) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C19 C18 C17 117.2(4) . . ? C19 C18 H18A 121.4 . . ? C17 C18 H18A 121.4 . . ? C18 C19 C14 121.9(4) . . ? C18 C19 N2 129.0(4) . . ? C14 C19 N2 109.1(3) . . ? O6 C20 N2 128.3(4) . . ? O6 C20 C13 124.3(4) . . ? N2 C20 C13 107.2(3) . . ? O7 C21 N2 118.3(4) . . ? O7 C21 C22 123.6(4) . . ? N2 C21 C22 118.1(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O4 C23 N1 117.9(4) . . ? O4 C23 C24 121.5(4) . . ? N1 C23 C24 120.6(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C6 C1 C2 C3 1.0(7) . . . . ? C8 C1 C2 C3 178.1(5) . . . . ? C1 C2 C3 C4 0.5(8) . . . . ? C2 C3 C4 C5 -1.8(9) . . . . ? C3 C4 C5 C6 1.4(7) . . . . ? C2 C1 C6 C5 -1.4(6) . . . . ? C8 C1 C6 C5 -179.0(4) . . . . ? C2 C1 C6 N1 178.9(4) . . . . ? C8 C1 C6 N1 1.3(5) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C4 C5 C6 N1 179.8(4) . . . . ? C7 N1 C6 C1 -4.0(4) . . . . ? C23 N1 C6 C1 -178.3(4) . . . . ? C7 N1 C6 C5 176.3(4) . . . . ? C23 N1 C6 C5 2.0(6) . . . . ? C23 N1 C7 O5 -3.6(7) . . . . ? C6 N1 C7 O5 -177.9(4) . . . . ? C23 N1 C7 C8 179.3(4) . . . . ? C6 N1 C7 C8 4.9(4) . . . . ? C10 O3 C8 C1 136.6(4) . . . . ? C10 O3 C8 C7 -107.1(3) . . . . ? C10 O3 C8 C9 6.4(3) . . . . ? C6 C1 C8 O3 122.6(4) . . . . ? C2 C1 C8 O3 -54.7(6) . . . . ? C6 C1 C8 C7 1.6(4) . . . . ? C2 C1 C8 C7 -175.7(5) . . . . ? C6 C1 C8 C9 -128.4(4) . . . . ? C2 C1 C8 C9 54.2(7) . . . . ? O5 C7 C8 O3 56.2(5) . . . . ? N1 C7 C8 O3 -126.5(4) . . . . ? O5 C7 C8 C1 178.7(4) . . . . ? N1 C7 C8 C1 -4.0(4) . . . . ? O5 C7 C8 C9 -42.9(6) . . . . ? N1 C7 C8 C9 134.3(3) . . . . ? O3 C8 C9 C12 98.1(4) . . . . ? C1 C8 C9 C12 -21.9(5) . . . . ? C7 C8 C9 C12 -148.6(3) . . . . ? O3 C8 C9 C10 -5.9(3) . . . . ? C1 C8 C9 C10 -125.9(4) . . . . ? C7 C8 C9 C10 107.4(4) . . . . ? C11 O2 C10 O3 92.4(4) . . . . ? C11 O2 C10 C9 -7.6(5) . . . . ? C8 O3 C10 O2 -117.7(4) . . . . ? C8 O3 C10 C9 -6.4(3) . . . . ? C12 C9 C10 O2 5.0(4) . . . . ? C8 C9 C10 O2 120.5(4) . . . . ? C12 C9 C10 O3 -109.5(3) . . . . ? C8 C9 C10 O3 6.0(3) . . . . ? C10 O2 C11 C12 7.1(5) . . . . ? C10 O2 C11 C13 100.2(4) . . . . ? C13 O1 C12 C9 112.1(3) . . . . ? C13 O1 C12 C11 4.3(3) . . . . ? C10 C9 C12 O1 -98.3(3) . . . . ? C8 C9 C12 O1 170.4(3) . . . . ? C10 C9 C12 C11 -0.8(4) . . . . ? C8 C9 C12 C11 -92.1(4) . . . . ? O2 C11 C12 O1 108.7(3) . . . . ? C13 C11 C12 O1 -3.9(3) . . . . ? O2 C11 C12 C9 -3.6(4) . . . . ? C13 C11 C12 C9 -116.2(3) . . . . ? C12 O1 C13 C14 -131.4(3) . . . . ? C12 O1 C13 C20 108.7(4) . . . . ? C12 O1 C13 C11 -4.2(3) . . . . ? O2 C11 C13 O1 -104.3(3) . . . . ? C12 C11 C13 O1 4.0(3) . . . . ? O2 C11 C13 C14 16.2(5) . . . . ? C12 C11 C13 C14 124.5(4) . . . . ? O2 C11 C13 C20 140.4(3) . . . . ? C12 C11 C13 C20 -111.4(3) . . . . ? O1 C13 C14 C15 50.0(6) . . . . ? C20 C13 C14 C15 175.0(4) . . . . ? C11 C13 C14 C15 -57.9(6) . . . . ? O1 C13 C14 C19 -126.3(3) . . . . ? C20 C13 C14 C19 -1.3(4) . . . . ? C11 C13 C14 C19 125.8(4) . . . . ? C19 C14 C15 C16 1.2(6) . . . . ? C13 C14 C15 C16 -174.7(4) . . . . ? C14 C15 C16 C17 -0.4(7) . . . . ? C15 C16 C17 C18 -1.1(7) . . . . ? C16 C17 C18 C19 1.8(7) . . . . ? C17 C18 C19 C14 -0.9(6) . . . . ? C17 C18 C19 N2 178.2(4) . . . . ? C15 C14 C19 C18 -0.6(6) . . . . ? C13 C14 C19 C18 176.2(4) . . . . ? C15 C14 C19 N2 -179.8(3) . . . . ? C13 C14 C19 N2 -3.1(4) . . . . ? C20 N2 C19 C18 -172.4(4) . . . . ? C21 N2 C19 C18 12.0(6) . . . . ? C20 N2 C19 C14 6.7(4) . . . . ? C21 N2 C19 C14 -168.8(4) . . . . ? C21 N2 C20 O6 -7.8(8) . . . . ? C19 N2 C20 O6 176.9(5) . . . . ? C21 N2 C20 C13 168.0(4) . . . . ? C19 N2 C20 C13 -7.4(4) . . . . ? O1 C13 C20 O6 -52.7(6) . . . . ? C14 C13 C20 O6 -178.7(5) . . . . ? C11 C13 C20 O6 46.8(6) . . . . ? O1 C13 C20 N2 131.3(3) . . . . ? C14 C13 C20 N2 5.3(4) . . . . ? C11 C13 C20 N2 -129.1(3) . . . . ? C20 N2 C21 O7 -168.8(4) . . . . ? C19 N2 C21 O7 6.0(6) . . . . ? C20 N2 C21 C22 12.8(6) . . . . ? C19 N2 C21 C22 -172.4(4) . . . . ? C7 N1 C23 O4 -161.1(5) . . . . ? C6 N1 C23 O4 12.2(7) . . . . ? C7 N1 C23 C24 20.0(7) . . . . ? C6 N1 C23 C24 -166.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.421 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.094 #cif file of compound 18 data_compound18 _database_code_CSD 175734 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3660(17) _cell_length_b 9.6653(19) _cell_length_c 9.7304(19) _cell_angle_alpha 68.82(3) _cell_angle_beta 68.35(3) _cell_angle_gamma 68.44(3) _cell_volume 656.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 15.660 _cell_measurement_theta_max 32.060 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type 'empirical psi-scan' _exptl_absorpt_correction_T_min 0.5457 _exptl_absorpt_correction_T_max 1.0000 _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 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'AFC5R (RIGAKU)' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 2224 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2099 _reflns_number_gt 1399 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'AFC5R (RIGAKU)' _computing_cell_refinement 'AFC5R (RIGAKU)' _computing_data_reduction 'Enraf-Nonius Molen/VAX Software' _computing_structure_solution 'SHELXTL (Sheldrick, 1994)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1994)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELXTL (Sheldrick, 1994)' _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^)+(0.1507P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.035(13) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2099 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1138 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2025 _refine_ls_wR_factor_gt 0.1933 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 0.1242(4) 0.6285(4) -0.1631(3) 0.0722(9) Uani 1 1 d . . . O2 O 0.1003(3) 0.7495(3) 0.0022(2) 0.0475(7) Uani 1 1 d . . . O3 O 0.4560(3) 0.8535(3) -0.1097(3) 0.0580(7) Uani 1 1 d . . . O4 O 0.6518(4) 0.5911(3) -0.2502(3) 0.0682(8) Uani 1 1 d . . . O5 O 0.5301(4) 0.7223(4) -0.6656(3) 0.0849(10) Uani 1 1 d . . . N N 0.4991(3) 0.7490(3) -0.4353(3) 0.0438(7) Uani 1 1 d . . . C1 C -0.1678(5) 0.7512(6) -0.0263(5) 0.0758(13) Uani 1 1 d . . . H1A H -0.2122 0.7147 -0.0809 0.114 Uiso 1 1 calc R . . H1B H -0.2077 0.8617 -0.0507 0.114 Uiso 1 1 calc R . . H1C H -0.2119 0.7097 0.0819 0.114 Uiso 1 1 calc R . . C2 C 0.0303(5) 0.7010(4) -0.0714(4) 0.0491(9) Uani 1 1 d . . . C3 C 0.2893(4) 0.7059(4) -0.0357(4) 0.0468(9) Uani 1 1 d . . . H3A H 0.3412 0.5943 -0.0196 0.056 Uiso 1 1 calc R . . C4 C 0.3606(5) 0.7758(6) 0.0383(4) 0.0670(12) Uani 1 1 d . . . H4A H 0.2680 0.8458 0.0960 0.080 Uiso 1 1 calc R . . H4B H 0.4384 0.6998 0.1000 0.080 Uiso 1 1 calc R . . C5 C 0.3867(4) 0.7994(4) -0.1900(4) 0.0429(8) Uani 1 1 d . . . C6 C 0.2855(4) 0.9197(4) -0.2979(4) 0.0413(8) Uani 1 1 d . . . C7 C 0.1467(5) 1.0478(4) -0.2734(4) 0.0533(9) Uani 1 1 d . . . H7A H 0.1031 1.0698 -0.1786 0.064 Uiso 1 1 calc R . . C8 C 0.0733(5) 1.1435(5) -0.3929(5) 0.0627(11) Uani 1 1 d . . . H8A H -0.0202 1.2312 -0.3793 0.075 Uiso 1 1 calc R . . C9 C 0.1387(5) 1.1086(5) -0.5317(5) 0.0622(11) Uani 1 1 d . . . H9A H 0.0861 1.1729 -0.6100 0.075 Uiso 1 1 calc R . . C10 C 0.2793(5) 0.9819(4) -0.5594(4) 0.0529(9) Uani 1 1 d . . . H10A H 0.3236 0.9614 -0.6548 0.063 Uiso 1 1 calc R . . C11 C 0.3526(4) 0.8857(4) -0.4383(3) 0.0410(8) Uani 1 1 d . . . C12 C 0.5316(4) 0.6982(4) -0.2902(4) 0.0456(8) Uani 1 1 d . . . C13 C 0.5855(5) 0.6754(5) -0.5542(4) 0.0554(10) Uani 1 1 d . . . C14 C 0.7434(6) 0.5368(5) -0.5361(5) 0.0775(13) Uani 1 1 d . . . H14A H 0.7892 0.4982 -0.6252 0.116 Uiso 1 1 calc R . . H14B H 0.7067 0.4581 -0.4471 0.116 Uiso 1 1 calc R . . H14C H 0.8349 0.5658 -0.5244 0.116 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 0.082(2) 0.081(2) 0.0656(18) -0.0348(17) -0.0195(15) -0.0198(16) O2 0.0469(13) 0.0588(16) 0.0362(12) -0.0122(11) -0.0128(10) -0.0123(11) O3 0.0606(15) 0.0817(19) 0.0432(13) -0.0125(12) -0.0260(11) -0.0238(13) O4 0.0565(16) 0.071(2) 0.0515(15) -0.0070(13) -0.0229(12) 0.0104(14) O5 0.098(2) 0.106(3) 0.0557(17) -0.0333(18) -0.0353(16) -0.0071(19) N 0.0419(15) 0.0501(17) 0.0331(13) -0.0048(12) -0.0148(11) -0.0070(12) C1 0.060(2) 0.100(4) 0.067(3) -0.008(2) -0.026(2) -0.028(2) C2 0.056(2) 0.055(2) 0.0395(18) -0.0077(16) -0.0192(16) -0.0159(17) C3 0.0424(18) 0.055(2) 0.0396(18) -0.0080(16) -0.0185(14) -0.0063(15) C4 0.061(2) 0.105(4) 0.0413(19) -0.017(2) -0.0179(17) -0.028(2) C5 0.0447(18) 0.051(2) 0.0347(16) -0.0064(14) -0.0201(13) -0.0107(15) C6 0.0427(17) 0.0386(18) 0.0404(17) -0.0018(14) -0.0200(13) -0.0080(14) C7 0.051(2) 0.052(2) 0.052(2) -0.0098(17) -0.0178(16) -0.0080(17) C8 0.054(2) 0.049(2) 0.069(3) 0.0016(19) -0.0293(19) -0.0014(17) C9 0.054(2) 0.064(3) 0.057(2) 0.0087(19) -0.0302(18) -0.0114(19) C10 0.058(2) 0.062(2) 0.0371(17) 0.0056(16) -0.0274(15) -0.0176(19) C11 0.0372(16) 0.0439(19) 0.0385(17) -0.0017(14) -0.0153(13) -0.0112(14) C12 0.0406(18) 0.051(2) 0.0336(16) -0.0023(15) -0.0138(13) -0.0053(16) C13 0.061(2) 0.060(2) 0.046(2) -0.0201(18) -0.0085(17) -0.0163(19) C14 0.078(3) 0.069(3) 0.074(3) -0.032(2) -0.020(2) 0.004(2) _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 C2 1.198(4) . ? O2 C2 1.352(4) . ? O2 C3 1.416(4) . ? O3 C5 1.440(4) . ? O3 C4 1.444(5) . ? O4 C12 1.211(4) . ? O5 C13 1.207(5) . ? N C13 1.402(5) . ? N C12 1.412(4) . ? N C11 1.434(4) . ? C1 C2 1.484(5) . ? C3 C4 1.515(5) . ? C3 C5 1.547(5) . ? C5 C6 1.490(4) . ? C5 C12 1.523(5) . ? C6 C7 1.376(5) . ? C6 C11 1.383(5) . ? C7 C8 1.385(5) . ? C8 C9 1.372(6) . ? C9 C10 1.379(6) . ? C10 C11 1.396(5) . ? C13 C14 1.507(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C3 115.1(3) . . ? C5 O3 C4 92.6(2) . . ? C13 N C12 126.8(3) . . ? C13 N C11 124.9(3) . . ? C12 N C11 108.2(3) . . ? O1 C2 O2 121.3(3) . . ? O1 C2 C1 126.7(4) . . ? O2 C2 C1 112.1(3) . . ? O2 C3 C4 112.9(3) . . ? O2 C3 C5 116.6(3) . . ? C4 C3 C5 85.9(3) . . ? O3 C4 C3 91.2(3) . . ? O3 C5 C6 116.5(3) . . ? O3 C5 C12 113.2(3) . . ? C6 C5 C12 103.3(3) . . ? O3 C5 C3 90.1(2) . . ? C6 C5 C3 120.9(3) . . ? C12 C5 C3 113.1(3) . . ? C7 C6 C11 121.5(3) . . ? C7 C6 C5 129.3(3) . . ? C11 C6 C5 109.2(3) . . ? C6 C7 C8 118.6(4) . . ? C9 C8 C7 119.9(4) . . ? C8 C9 C10 122.6(4) . . ? C9 C10 C11 117.3(3) . . ? C6 C11 C10 120.2(3) . . ? C6 C11 N 110.6(3) . . ? C10 C11 N 129.2(3) . . ? O4 C12 N 126.3(3) . . ? O4 C12 C5 125.4(3) . . ? N C12 C5 108.3(3) . . ? O5 C13 N 119.6(4) . . ? O5 C13 C14 122.1(4) . . ? N C13 C14 118.3(4) . . ? _diffrn_measured_fraction_theta_max 0.811 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.811 _refine_diff_density_max 0.408 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.079 #cif file of compound 27 data_compound27 _database_code_CSD 175735 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O6' _chemical_formula_weight 397.41 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.817(1) _cell_length_b 11.7579(6) _cell_length_c 8.9452(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.358(2) _cell_angle_gamma 90.00 _cell_volume 2071.47(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2531 _cell_measurement_theta_min 1.03 _cell_measurement_theta_max 29.56 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 11292 _diffrn_reflns_av_R_equivalents 0.1930 _diffrn_reflns_av_sigmaI/netI 0.2061 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3650 _reflns_number_gt 1322 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.1912P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.078(10) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3650 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2382 _refine_ls_R_factor_gt 0.1173 _refine_ls_wR_factor_ref 0.3411 _refine_ls_wR_factor_gt 0.2726 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.880 _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 0.3208(2) 0.0858(5) 0.1028(5) 0.0846(16) Uani 1 1 d . . . O2 O 0.3108(2) 0.2643(4) 0.2144(5) 0.0827(16) Uani 1 1 d . . . O3 O 0.13766(19) 0.2375(3) 0.0415(4) 0.0627(13) Uani 1 1 d . . . H3A H 0.0990 0.2401 -0.0019 0.094 Uiso 1 1 calc R . . O4 O 0.0761(2) 0.1241(4) 0.2898(5) 0.0752(15) Uani 1 1 d . . . O5 O 0.0001(2) -0.1711(4) 0.0902(5) 0.0732(14) Uani 1 1 d . . . C1 C 0.1086(3) -0.0500(5) -0.0075(6) 0.0445(15) Uani 1 1 d . . . N1 N 0.0756(2) -0.0280(4) 0.1240(4) 0.0451(13) Uani 1 1 d . . . C2 C 0.1018(3) -0.1423(5) -0.1035(7) 0.0616(18) Uani 1 1 d . . . H2A H 0.0724 -0.2018 -0.0879 0.074 Uiso 1 1 calc R . . C3 C 0.1398(4) -0.1433(7) -0.2224(7) 0.074(2) Uani 1 1 d . . . H3B H 0.1351 -0.2041 -0.2891 0.089 Uiso 1 1 calc R . . C4 C 0.1841(4) -0.0583(7) -0.2466(7) 0.076(2) Uani 1 1 d . . . H4A H 0.2097 -0.0623 -0.3276 0.091 Uiso 1 1 calc R . . C5 C 0.1909(3) 0.0343(6) -0.1498(6) 0.0587(17) Uani 1 1 d . . . H5A H 0.2206 0.0931 -0.1661 0.070 Uiso 1 1 calc R . . C6 C 0.1532(3) 0.0384(5) -0.0289(6) 0.0463(15) Uani 1 1 d . . . C7 C 0.1521(3) 0.1263(5) 0.0924(6) 0.0459(15) Uani 1 1 d . . . C8 C 0.0963(3) 0.0781(5) 0.1833(7) 0.0511(16) Uani 1 1 d . . . C9 C 0.2183(3) 0.1345(6) 0.1997(7) 0.0553(17) Uani 1 1 d . . . H9A H 0.2107 0.1838 0.2846 0.066 Uiso 1 1 calc R . . C10 C 0.2450(3) 0.0227(6) 0.2586(7) 0.0559(17) Uani 1 1 d . . . C11 C 0.2222(4) -0.0527(6) 0.3596(8) 0.074(2) Uani 1 1 d . . . H11A H 0.1832 -0.0360 0.4043 0.088 Uiso 1 1 calc R . . C12 C 0.2554(5) -0.1489(9) 0.3939(9) 0.101(3) Uani 1 1 d . . . H12A H 0.2390 -0.2003 0.4602 0.121 Uiso 1 1 calc R . . C13 C 0.3138(6) -0.1724(8) 0.3312(12) 0.120(4) Uani 1 1 d . . . H13A H 0.3364 -0.2400 0.3576 0.144 Uiso 1 1 calc R . . C14 C 0.3418(4) -0.0985(9) 0.2275(11) 0.112(3) Uani 1 1 d . . . H14A H 0.3810 -0.1151 0.1834 0.134 Uiso 1 1 calc R . . C15 C 0.3046(4) 0.0011(7) 0.1988(8) 0.076(2) Uani 1 1 d . . . C16 C 0.2765(3) 0.1813(6) 0.1228(8) 0.0680(19) Uani 1 1 d . . . H16A H 0.2596 0.2140 0.0250 0.082 Uiso 1 1 calc R . . C17 C 0.3621(5) 0.3235(9) 0.1329(11) 0.121(4) Uani 1 1 d . . . H17A H 0.3987 0.2717 0.1164 0.145 Uiso 1 1 calc R . . H17B H 0.3414 0.3501 0.0359 0.145 Uiso 1 1 calc R . . C18 C 0.3883(6) 0.4190(11) 0.2246(14) 0.178(6) Uani 1 1 d . . . H18A H 0.4106 0.3886 0.3181 0.213 Uiso 1 1 calc R . . H18B H 0.3498 0.4630 0.2497 0.213 Uiso 1 1 calc R . . C19 C 0.4404(8) 0.5055(18) 0.1582(18) 0.316(13) Uani 1 1 d . . . H19A H 0.4221 0.5070 0.0531 0.379 Uiso 1 1 calc R . . H19B H 0.4804 0.4578 0.1605 0.379 Uiso 1 1 calc R . . C20 C 0.4811(2) 0.6521(4) 0.1782(5) 0.311(14) Uani 1 1 d . . . H20A H 0.5282 0.6545 0.1582 0.373 Uiso 1 1 calc R . . H20B H 0.4546 0.7124 0.1261 0.373 Uiso 1 1 calc R . . C21 C 0.0237(2) -0.0940(4) 0.1715(5) 0.0542(16) Uani 1 1 d R . . C22 C 0.0000(2) -0.0727(4) 0.3204(5) 0.075(2) Uani 1 1 d R . . H22A H -0.0356 -0.1253 0.3361 0.112 Uiso 1 1 calc R . . H22B H -0.0168 0.0036 0.3239 0.112 Uiso 1 1 calc R . . H22C H 0.0372 -0.0828 0.3977 0.112 Uiso 1 1 calc R . . O6 O 0.4693(3) 0.6374(6) 0.3702(9) 0.149(3) Uani 1 1 d . . . H6A H 0.4819 0.6955 0.4155 0.223 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 0.060(3) 0.110(4) 0.086(4) -0.007(3) 0.020(3) 0.005(3) O2 0.063(3) 0.092(4) 0.092(3) -0.016(3) 0.003(3) -0.023(3) O3 0.060(3) 0.051(3) 0.074(3) 0.006(2) -0.002(2) -0.005(2) O4 0.076(3) 0.089(4) 0.064(3) -0.030(3) 0.022(2) -0.008(3) O5 0.069(3) 0.071(3) 0.081(3) -0.002(3) 0.016(2) -0.016(2) C1 0.049(4) 0.050(4) 0.034(3) -0.003(3) 0.000(3) 0.005(3) N1 0.050(3) 0.048(3) 0.038(3) -0.007(2) 0.006(2) -0.006(2) C2 0.064(4) 0.061(4) 0.061(4) -0.005(3) 0.011(3) -0.003(3) C3 0.084(5) 0.082(5) 0.056(4) -0.021(4) 0.009(4) -0.001(4) C4 0.074(5) 0.109(6) 0.046(4) -0.015(4) 0.017(3) -0.001(5) C5 0.062(4) 0.067(5) 0.049(4) 0.002(3) 0.012(3) -0.002(3) C6 0.044(4) 0.057(4) 0.038(3) 0.002(3) 0.003(3) -0.002(3) C7 0.042(4) 0.044(4) 0.052(4) -0.005(3) 0.006(3) -0.007(3) C8 0.043(4) 0.056(4) 0.052(4) -0.012(3) -0.005(3) 0.001(3) C9 0.035(4) 0.074(4) 0.056(4) -0.012(3) 0.001(3) -0.008(3) C10 0.048(4) 0.066(4) 0.051(4) -0.003(3) -0.010(3) -0.004(3) C11 0.083(5) 0.070(5) 0.063(4) 0.001(4) -0.011(4) 0.013(4) C12 0.099(7) 0.123(9) 0.080(6) 0.012(5) 0.005(5) 0.004(6) C13 0.162(11) 0.069(6) 0.120(8) 0.011(6) -0.021(7) 0.024(6) C14 0.087(7) 0.114(8) 0.132(8) -0.015(7) 0.003(6) 0.041(6) C15 0.065(5) 0.091(6) 0.068(5) -0.007(4) -0.008(4) -0.001(5) C16 0.046(4) 0.083(5) 0.074(5) 0.000(4) 0.000(3) -0.003(4) C17 0.096(7) 0.138(9) 0.128(8) -0.011(6) 0.012(6) -0.071(6) C18 0.164(11) 0.168(12) 0.217(13) -0.042(10) 0.093(10) -0.075(9) C19 0.202(16) 0.53(4) 0.235(18) 0.06(2) 0.119(14) -0.09(2) C20 0.138(12) 0.36(3) 0.44(3) -0.30(2) 0.037(15) 0.001(14) C21 0.056(4) 0.052(4) 0.053(4) 0.002(3) 0.000(3) 0.005(3) C22 0.077(5) 0.099(6) 0.052(4) 0.012(4) 0.025(4) 0.003(4) O6 0.087(4) 0.139(6) 0.217(8) -0.039(5) -0.001(5) -0.039(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.376(9) . ? O1 C16 1.448(8) . ? O2 C16 1.400(8) . ? O2 C17 1.488(9) . ? O3 C7 1.403(7) . ? O3 H3A 0.8200 . ? O4 C8 1.203(6) . ? O5 C21 1.222(6) . ? C1 C2 1.381(8) . ? C1 C6 1.391(8) . ? C1 N1 1.430(6) . ? N1 C21 1.394(6) . ? N1 C8 1.399(7) . ? C2 C3 1.369(8) . ? C2 H2A 0.9300 . ? C3 C4 1.364(9) . ? C3 H3B 0.9300 . ? C4 C5 1.388(9) . ? C4 H4A 0.9300 . ? C5 C6 1.381(7) . ? C5 H5A 0.9300 . ? C6 C7 1.501(8) . ? C7 C9 1.541(8) . ? C7 C8 1.550(8) . ? C9 C10 1.491(8) . ? C9 C16 1.512(8) . ? C9 H9A 0.9800 . ? C10 C15 1.373(9) . ? C10 C11 1.377(9) . ? C11 C12 1.328(11) . ? C11 H11A 0.9300 . ? C12 C13 1.369(11) . ? C12 H12A 0.9300 . ? C13 C14 1.428(12) . ? C13 H13A 0.9300 . ? C14 C15 1.392(11) . ? C14 H14A 0.9300 . ? C16 H16A 0.9800 . ? C17 C18 1.453(13) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.608(16) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.904(19) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 O6 1.767(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.4811 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O6 H6A 0.8200 . ? 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 C15 O1 C16 107.3(5) . . ? C16 O2 C17 110.6(5) . . ? C7 O3 H3A 109.5 . . ? C2 C1 C6 121.4(5) . . ? C2 C1 N1 129.2(5) . . ? C6 C1 N1 109.4(5) . . ? C21 N1 C8 125.2(4) . . ? C21 N1 C1 124.8(4) . . ? C8 N1 C1 109.4(5) . . ? C3 C2 C1 117.8(6) . . ? C3 C2 H2A 121.1 . . ? C1 C2 H2A 121.1 . . ? C4 C3 C2 122.4(6) . . ? C4 C3 H3B 118.8 . . ? C2 C3 H3B 118.8 . . ? C3 C4 C5 119.7(6) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C6 C5 C4 119.5(6) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C1 119.3(5) . . ? C5 C6 C7 129.9(5) . . ? C1 C6 C7 110.8(4) . . ? O3 C7 C6 115.2(5) . . ? O3 C7 C9 105.8(4) . . ? C6 C7 C9 114.5(5) . . ? O3 C7 C8 112.3(4) . . ? C6 C7 C8 101.2(4) . . ? C9 C7 C8 107.6(5) . . ? O4 C8 N1 126.3(5) . . ? O4 C8 C7 124.8(5) . . ? N1 C8 C7 108.9(5) . . ? C10 C9 C16 102.9(5) . . ? C10 C9 C7 114.2(5) . . ? C16 C9 C7 112.3(5) . . ? C10 C9 H9A 109.1 . . ? C16 C9 H9A 109.1 . . ? C7 C9 H9A 109.1 . . ? C15 C10 C11 119.7(7) . . ? C15 C10 C9 108.2(6) . . ? C11 C10 C9 132.0(6) . . ? C12 C11 C10 120.7(8) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 119.8(9) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C14 123.4(8) . . ? C12 C13 H13A 118.3 . . ? C14 C13 H13A 118.3 . . ? C15 C14 C13 113.3(8) . . ? C15 C14 H14A 123.3 . . ? C13 C14 H14A 123.3 . . ? C10 C15 O1 112.3(7) . . ? C10 C15 C14 123.0(8) . . ? O1 C15 C14 124.6(8) . . ? O2 C16 O1 110.6(5) . . ? O2 C16 C9 109.4(5) . . ? O1 C16 C9 106.1(5) . . ? O2 C16 H16A 110.2 . . ? O1 C16 H16A 110.2 . . ? C9 C16 H16A 110.2 . . ? C18 C17 O2 107.8(8) . . ? C18 C17 H17A 110.1 . . ? O2 C17 H17A 110.1 . . ? C18 C17 H17B 110.1 . . ? O2 C17 H17B 110.1 . . ? H17A C17 H17B 108.5 . . ? C17 C18 C19 119.0(11) . . ? C17 C18 H18A 107.6 . . ? C19 C18 H18A 107.6 . . ? C17 C18 H18B 107.6 . . ? C19 C18 H18B 107.6 . . ? H18A C18 H18B 107.0 . . ? C18 C19 C20 145.1(12) . . ? C18 C19 H19A 100.6 . . ? C20 C19 H19A 100.6 . . ? C18 C19 H19B 100.6 . . ? C20 C19 H19B 100.6 . . ? H19A C19 H19B 104.3 . . ? O6 C20 C19 84.4(5) . . ? O6 C20 H20A 114.6 . . ? C19 C20 H20A 114.6 . . ? O6 C20 H20B 114.6 . . ? C19 C20 H20B 114.6 . . ? H20A C20 H20B 111.7 . . ? O5 C21 N1 118.6(4) . . ? O5 C21 C22 121.5(3) . . ? N1 C21 C22 119.9(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 O6 H6A 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 C1 N1 C21 -6.8(9) . . . . ? C6 C1 N1 C21 174.4(5) . . . . ? C2 C1 N1 C8 -178.1(6) . . . . ? C6 C1 N1 C8 3.1(6) . . . . ? C6 C1 C2 C3 -1.0(9) . . . . ? N1 C1 C2 C3 -179.7(6) . . . . ? C1 C2 C3 C4 1.2(10) . . . . ? C2 C3 C4 C5 -1.1(11) . . . . ? C3 C4 C5 C6 0.8(10) . . . . ? C4 C5 C6 C1 -0.6(9) . . . . ? C4 C5 C6 C7 178.7(6) . . . . ? C2 C1 C6 C5 0.7(8) . . . . ? N1 C1 C6 C5 179.7(5) . . . . ? C2 C1 C6 C7 -178.7(5) . . . . ? N1 C1 C6 C7 0.3(6) . . . . ? C5 C6 C7 O3 56.1(8) . . . . ? C1 C6 C7 O3 -124.6(5) . . . . ? C5 C6 C7 C9 -67.0(8) . . . . ? C1 C6 C7 C9 112.4(5) . . . . ? C5 C6 C7 C8 177.6(6) . . . . ? C1 C6 C7 C8 -3.1(6) . . . . ? C21 N1 C8 O4 5.5(9) . . . . ? C1 N1 C8 O4 176.7(6) . . . . ? C21 N1 C8 C7 -176.3(5) . . . . ? C1 N1 C8 C7 -5.1(6) . . . . ? O3 C7 C8 O4 -53.4(8) . . . . ? C6 C7 C8 O4 -176.9(6) . . . . ? C9 C7 C8 O4 62.7(7) . . . . ? O3 C7 C8 N1 128.4(5) . . . . ? C6 C7 C8 N1 4.9(6) . . . . ? C9 C7 C8 N1 -115.5(5) . . . . ? O3 C7 C9 C10 -176.1(5) . . . . ? C6 C7 C9 C10 -48.1(7) . . . . ? C8 C7 C9 C10 63.6(6) . . . . ? O3 C7 C9 C16 -59.5(6) . . . . ? C6 C7 C9 C16 68.5(7) . . . . ? C8 C7 C9 C16 -179.8(5) . . . . ? C16 C9 C10 C15 -9.8(6) . . . . ? C7 C9 C10 C15 112.2(6) . . . . ? C16 C9 C10 C11 167.4(7) . . . . ? C7 C9 C10 C11 -70.7(8) . . . . ? C15 C10 C11 C12 -3.5(10) . . . . ? C9 C10 C11 C12 179.7(7) . . . . ? C10 C11 C12 C13 1.6(12) . . . . ? C11 C12 C13 C14 -0.6(15) . . . . ? C12 C13 C14 C15 1.3(14) . . . . ? C11 C10 C15 O1 -178.6(6) . . . . ? C9 C10 C15 O1 -1.1(7) . . . . ? C11 C10 C15 C14 4.4(10) . . . . ? C9 C10 C15 C14 -178.0(7) . . . . ? C16 O1 C15 C10 12.1(7) . . . . ? C16 O1 C15 C14 -171.0(7) . . . . ? C13 C14 C15 C10 -3.2(11) . . . . ? C13 C14 C15 O1 -179.8(7) . . . . ? C17 O2 C16 O1 71.5(8) . . . . ? C17 O2 C16 C9 -172.0(6) . . . . ? C15 O1 C16 O2 100.7(6) . . . . ? C15 O1 C16 C9 -17.8(7) . . . . ? C10 C9 C16 O2 -102.8(6) . . . . ? C7 C9 C16 O2 134.0(6) . . . . ? C10 C9 C16 O1 16.5(6) . . . . ? C7 C9 C16 O1 -106.7(6) . . . . ? C16 O2 C17 C18 171.5(9) . . . . ? O2 C17 C18 C19 -174.8(13) . . . . ? C17 C18 C19 C20 162.7(18) . . . . ? C18 C19 C20 O6 28(2) . . . . ? C8 N1 C21 O5 163.5(5) . . . . ? C1 N1 C21 O5 -6.4(7) . . . . ? C8 N1 C21 C22 -18.8(6) . . . . ? C1 N1 C21 C22 171.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.863 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.180 #cif file of compound 17 data_compound17 _database_code_CSD 175736 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N O4' _chemical_formula_weight 289.32 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2141(8) _cell_length_b 8.7676(8) _cell_length_c 12.0117(11) _cell_angle_alpha 104.046(2) _cell_angle_beta 105.633(2) _cell_angle_gamma 101.122(2) _cell_volume 776.65(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1749 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 28.30 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 4387 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.1095 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2676 _reflns_number_gt 1305 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.1397P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.051(12) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2676 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1514 _refine_ls_R_factor_gt 0.0835 _refine_ls_wR_factor_ref 0.2592 _refine_ls_wR_factor_gt 0.2189 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 -0.1696(4) 0.3746(4) 0.5150(3) 0.0809(10) Uani 1 1 d . . . O2 O 0.2658(5) 0.1886(5) 0.5929(3) 0.0929(12) Uani 1 1 d . . . O3 O 0.2406(4) -0.0576(3) 0.3702(3) 0.0755(10) Uani 1 1 d . . . O4 O 0.3586(3) 0.2288(4) 0.2601(3) 0.0648(9) Uani 1 1 d . . . N1 N 0.0134(4) 0.2257(4) 0.4671(3) 0.0534(9) Uani 1 1 d . . . C1 C 0.0208(5) 0.0808(5) 0.2814(4) 0.0540(11) Uani 1 1 d . . . C2 C -0.0442(6) 0.0022(6) 0.1564(4) 0.0706(13) Uani 1 1 d . . . H2A H 0.0186 -0.0577 0.1183 0.085 Uiso 1 1 calc R . . C3 C -0.2041(6) 0.0153(6) 0.0903(4) 0.0847(15) Uani 1 1 d . . . H3A H -0.2488 -0.0337 0.0064 0.102 Uiso 1 1 calc R . . C4 C -0.2978(6) 0.1011(7) 0.1488(5) 0.0829(15) Uani 1 1 d . . . H4A H -0.4056 0.1077 0.1029 0.099 Uiso 1 1 calc R . . C5 C -0.2378(5) 0.1765(5) 0.2715(4) 0.0664(13) Uani 1 1 d . . . H5A H -0.3028 0.2338 0.3091 0.080 Uiso 1 1 calc R . . C6 C -0.0763(5) 0.1648(5) 0.3385(4) 0.0504(10) Uani 1 1 d . . . C7 C -0.0378(6) 0.3307(5) 0.5517(4) 0.0611(12) Uani 1 1 d . . . C8 C 0.0724(6) 0.3860(6) 0.6821(4) 0.0817(14) Uani 1 1 d . . . H8A H 0.1687 0.3378 0.6915 0.122 Uiso 1 1 calc R . . H8B H 0.0025 0.3530 0.7290 0.122 Uiso 1 1 calc R . . H8C H 0.1173 0.5030 0.7099 0.122 Uiso 1 1 calc R . . C9 C 0.1668(5) 0.1720(5) 0.4934(4) 0.0582(11) Uani 1 1 d . . . C10 C 0.1886(5) 0.0905(5) 0.3729(4) 0.0543(11) Uani 1 1 d . . . C11 C 0.3927(6) 0.0006(6) 0.3373(5) 0.0814(15) Uani 1 1 d . . . H11A H 0.3798 -0.0531 0.2534 0.098 Uiso 1 1 calc R . . H11B H 0.5021 -0.0026 0.3920 0.098 Uiso 1 1 calc R . . C12 C 0.3672(5) 0.1705(5) 0.3586(4) 0.0598(12) Uani 1 1 d . . . H12A H 0.4514 0.2487 0.4350 0.072 Uiso 1 1 calc R . . C13 C 0.3537(7) 0.3948(6) 0.2852(5) 0.0968(17) Uani 1 1 d . . . H13A H 0.4637 0.4669 0.3450 0.116 Uiso 1 1 calc R . . H13B H 0.2585 0.4101 0.3162 0.116 Uiso 1 1 calc R . . C14 C 0.3240(15) 0.4302(10) 0.1628(9) 0.195(5) Uani 1 1 d . . . H14A H 0.4190 0.4078 0.1339 0.234 Uiso 1 1 calc R . . H14B H 0.2162 0.3514 0.1053 0.234 Uiso 1 1 calc R . . C15 C 0.3141(18) 0.5639(17) 0.1574(10) 0.238(6) Uani 1 1 d . . . H15A H 0.4214 0.6435 0.2148 0.285 Uiso 1 1 calc R . . H15B H 0.2180 0.5865 0.1849 0.285 Uiso 1 1 calc R . . C16 C 0.2861(17) 0.5927(17) 0.0331(9) 0.269(7) Uani 1 1 d . . . H16A H 0.2806 0.7031 0.0410 0.403 Uiso 1 1 calc R . . H16B H 0.1780 0.5180 -0.0245 0.403 Uiso 1 1 calc R . . H16C H 0.3822 0.5751 0.0054 0.403 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 0.072(2) 0.086(2) 0.102(2) 0.0288(19) 0.0429(19) 0.0422(18) O2 0.084(2) 0.137(3) 0.073(2) 0.042(2) 0.0206(19) 0.061(2) O3 0.068(2) 0.059(2) 0.117(2) 0.0394(18) 0.0383(18) 0.0322(15) O4 0.0522(17) 0.078(2) 0.082(2) 0.0375(17) 0.0336(15) 0.0277(15) N1 0.0411(18) 0.061(2) 0.062(2) 0.0202(17) 0.0199(16) 0.0173(16) C1 0.035(2) 0.055(3) 0.075(3) 0.025(2) 0.019(2) 0.0124(18) C2 0.050(3) 0.077(3) 0.075(3) 0.009(3) 0.019(2) 0.017(2) C3 0.059(3) 0.101(4) 0.070(3) 0.009(3) 0.004(3) 0.016(3) C4 0.040(3) 0.102(4) 0.086(4) 0.018(3) 0.002(3) 0.017(3) C5 0.035(2) 0.074(3) 0.088(3) 0.021(3) 0.018(2) 0.019(2) C6 0.035(2) 0.049(2) 0.066(3) 0.019(2) 0.0168(19) 0.0080(17) C7 0.055(3) 0.058(3) 0.077(3) 0.021(2) 0.033(2) 0.014(2) C8 0.078(3) 0.079(3) 0.079(3) 0.011(3) 0.030(3) 0.013(3) C9 0.047(2) 0.064(3) 0.070(3) 0.030(2) 0.018(2) 0.021(2) C10 0.045(2) 0.055(3) 0.072(3) 0.026(2) 0.023(2) 0.0235(19) C11 0.070(3) 0.085(4) 0.121(4) 0.048(3) 0.049(3) 0.048(3) C12 0.038(2) 0.071(3) 0.075(3) 0.029(2) 0.017(2) 0.020(2) C13 0.097(4) 0.080(4) 0.146(5) 0.060(4) 0.059(4) 0.039(3) C14 0.305(13) 0.128(7) 0.242(10) 0.139(7) 0.115(9) 0.122(8) C15 0.282(15) 0.306(17) 0.204(10) 0.140(12) 0.099(10) 0.153(13) C16 0.348(17) 0.379(18) 0.171(8) 0.194(10) 0.094(9) 0.155(14) _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 C7 1.225(5) . ? O2 C9 1.207(4) . ? O3 C10 1.439(4) . ? O3 C11 1.448(5) . ? O4 C12 1.389(5) . ? O4 C13 1.424(5) . ? N1 C7 1.409(5) . ? N1 C9 1.413(5) . ? N1 C6 1.431(5) . ? C1 C6 1.388(5) . ? C1 C2 1.392(6) . ? C1 C10 1.486(5) . ? C2 C3 1.382(6) . ? C2 H2A 0.9300 . ? C3 C4 1.382(6) . ? C3 H3A 0.9300 . ? C4 C5 1.365(6) . ? C4 H4A 0.9300 . ? C5 C6 1.391(5) . ? C5 H5A 0.9300 . ? C7 C8 1.485(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.525(6) . ? C10 C12 1.571(6) . ? C11 C12 1.514(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9800 . ? C13 C14 1.541(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.206(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.538(12) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O3 C11 92.5(3) . . ? C12 O4 C13 113.4(4) . . ? C7 N1 C9 125.9(3) . . ? C7 N1 C6 125.1(3) . . ? C9 N1 C6 108.8(3) . . ? C6 C1 C2 120.6(3) . . ? C6 C1 C10 109.7(3) . . ? C2 C1 C10 129.7(4) . . ? C3 C2 C1 118.4(4) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C4 C3 C2 120.0(4) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C5 C4 C3 122.4(4) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C4 C5 C6 117.8(4) . . ? C4 C5 H5A 121.1 . . ? C6 C5 H5A 121.1 . . ? C1 C6 C5 120.7(4) . . ? C1 C6 N1 109.8(3) . . ? C5 C6 N1 129.5(4) . . ? O1 C7 N1 118.9(4) . . ? O1 C7 C8 122.6(4) . . ? N1 C7 C8 118.4(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N1 126.8(4) . . ? O2 C9 C10 125.3(4) . . ? N1 C9 C10 107.9(3) . . ? O3 C10 C1 118.3(3) . . ? O3 C10 C9 113.1(3) . . ? C1 C10 C9 103.1(3) . . ? O3 C10 C12 89.6(3) . . ? C1 C10 C12 118.9(3) . . ? C9 C10 C12 114.3(3) . . ? O3 C11 C12 91.6(3) . . ? O3 C11 H11A 113.4 . . ? C12 C11 H11A 113.4 . . ? O3 C11 H11B 113.4 . . ? C12 C11 H11B 113.4 . . ? H11A C11 H11B 110.7 . . ? O4 C12 C11 113.8(4) . . ? O4 C12 C10 117.6(3) . . ? C11 C12 C10 85.0(3) . . ? O4 C12 H12A 112.6 . . ? C11 C12 H12A 112.6 . . ? C10 C12 H12A 112.6 . . ? O4 C13 C14 105.6(5) . . ? O4 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? O4 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 119.9(10) . . ? C15 C14 H14A 107.4 . . ? C13 C14 H14A 107.4 . . ? C15 C14 H14B 107.4 . . ? C13 C14 H14B 107.4 . . ? H14A C14 H14B 106.9 . . ? C14 C15 C16 117.6(13) . . ? C14 C15 H15A 107.9 . . ? C16 C15 H15A 107.9 . . ? C14 C15 H15B 107.9 . . ? C16 C15 H15B 107.9 . . ? H15A C15 H15B 107.2 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.4(6) . . . . ? C10 C1 C2 C3 -178.3(4) . . . . ? C1 C2 C3 C4 -1.7(7) . . . . ? C2 C3 C4 C5 0.6(8) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C2 C1 C6 C5 -2.0(6) . . . . ? C10 C1 C6 C5 178.6(3) . . . . ? C2 C1 C6 N1 176.5(4) . . . . ? C10 C1 C6 N1 -2.9(4) . . . . ? C4 C5 C6 C1 0.8(6) . . . . ? C4 C5 C6 N1 -177.3(4) . . . . ? C7 N1 C6 C1 173.1(4) . . . . ? C9 N1 C6 C1 -3.1(4) . . . . ? C7 N1 C6 C5 -8.7(6) . . . . ? C9 N1 C6 C5 175.2(4) . . . . ? C9 N1 C7 O1 176.0(4) . . . . ? C6 N1 C7 O1 0.4(6) . . . . ? C9 N1 C7 C8 -3.0(6) . . . . ? C6 N1 C7 C8 -178.5(4) . . . . ? C7 N1 C9 O2 10.6(7) . . . . ? C6 N1 C9 O2 -173.3(4) . . . . ? C7 N1 C9 C10 -168.5(4) . . . . ? C6 N1 C9 C10 7.6(4) . . . . ? C11 O3 C10 C1 114.3(4) . . . . ? C11 O3 C10 C9 -125.1(4) . . . . ? C11 O3 C10 C12 -8.7(3) . . . . ? C6 C1 C10 O3 132.8(4) . . . . ? C2 C1 C10 O3 -46.5(6) . . . . ? C6 C1 C10 C9 7.2(4) . . . . ? C2 C1 C10 C9 -172.1(4) . . . . ? C6 C1 C10 C12 -120.4(4) . . . . ? C2 C1 C10 C12 60.3(6) . . . . ? O2 C9 C10 O3 43.1(6) . . . . ? N1 C9 C10 O3 -137.8(3) . . . . ? O2 C9 C10 C1 171.9(4) . . . . ? N1 C9 C10 C1 -9.0(4) . . . . ? O2 C9 C10 C12 -57.6(6) . . . . ? N1 C9 C10 C12 121.5(3) . . . . ? C10 O3 C11 C12 9.0(3) . . . . ? C13 O4 C12 C11 -173.6(4) . . . . ? C13 O4 C12 C10 89.4(4) . . . . ? O3 C11 C12 O4 -126.3(4) . . . . ? O3 C11 C12 C10 -8.3(3) . . . . ? O3 C10 C12 O4 122.6(4) . . . . ? C1 C10 C12 O4 0.1(5) . . . . ? C9 C10 C12 O4 -122.1(4) . . . . ? O3 C10 C12 C11 8.3(3) . . . . ? C1 C10 C12 C11 -114.2(4) . . . . ? C9 C10 C12 C11 123.7(4) . . . . ? C12 O4 C13 C14 -173.9(5) . . . . ? O4 C13 C14 C15 179.9(12) . . . . ? C13 C14 C15 C16 179.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.420 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.070