# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Xianxiu Xu' _publ_contact_author_email XUXX677@NENU.EDU.CN _publ_section_title ; Tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition: highly diastereoselective one pot synthesis of fused oxazolines ; loop_ _publ_author_name 'Xianxiu Xu' 'Qun Liu' 'Ling Pan' 'Jing Tan' 'Wenming Xia' ; Lingjuan Zhang ; # Attachment '2a.cif' data_xx _database_code_depnum_ccdc_archive 'CCDC 753607' #TrackingRef '2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C100 H92 N4 O16 S8' _chemical_formula_weight 1862.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 24.784(5) _cell_length_b 15.750(5) _cell_length_c 23.149(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 9036(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 156 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3904 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.802 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11185 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3965 _reflns_number_gt 2710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0359P)^2^+4.5686P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(9) _refine_ls_number_reflns 3965 _refine_ls_number_parameters 290 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.08105(5) 0.98858(7) 1.63817(5) 0.0656(3) Uani 1 1 d . . . S2 S 1.08632(6) 1.16685(7) 1.67147(5) 0.0772(4) Uani 1 1 d . . . O2 O 1.11666(11) 1.25420(16) 1.56374(12) 0.0608(7) Uani 1 1 d . B . O1 O 1.06996(13) 0.97769(17) 1.52786(13) 0.0763(9) Uani 1 1 d . . . O4 O 0.98935(11) 1.31264(15) 1.45757(14) 0.0664(8) Uani 1 1 d . . . C7 C 1.04005(16) 1.1625(2) 1.44279(18) 0.0551(10) Uani 1 1 d . B . H7 H 1.0034 1.1569 1.4583 0.066 Uiso 1 1 calc R . . C10 C 1.07101(14) 1.1185(2) 1.55963(16) 0.0433(9) Uani 1 1 d . . . C14 C 1.06621(15) 1.2141(2) 1.54522(16) 0.0455(10) Uani 1 1 d . B . C21 C 0.97051(16) 1.2150(2) 1.58016(17) 0.0533(10) Uani 1 1 d . B . H21 H 0.9678 1.1589 1.5680 0.064 Uiso 1 1 calc R . . O3 O 1.06760(11) 1.38391(16) 1.46241(14) 0.0719(9) Uani 1 1 d . . . C17 C 1.04294(17) 1.3190(2) 1.46533(18) 0.0535(10) Uani 1 1 d . B . C20 C 1.01945(16) 1.2571(2) 1.57532(16) 0.0500(10) Uani 1 1 d . . . C9 C 1.06920(16) 1.0537(3) 1.51554(17) 0.0540(10) Uani 1 1 d . B . C15 C 1.06802(15) 1.2314(2) 1.47855(17) 0.0484(10) Uani 1 1 d . . . N1 N 1.12660(13) 1.2410(2) 1.46646(16) 0.0612(9) Uani 1 1 d . B . C8 C 1.06793(17) 1.0788(2) 1.45332(19) 0.0641(12) Uani 1 1 d . . . H8A H 1.0496 1.0349 1.4315 0.077 Uiso 1 1 calc R B . H8B H 1.1047 1.0823 1.4390 0.077 Uiso 1 1 calc R . . C6 C 1.03412(18) 1.1825(2) 1.37908(19) 0.0570(11) Uani 1 1 d . . . C25 C 1.02265(19) 1.3396(3) 1.5956(2) 0.0765(14) Uani 1 1 d . B . H25 H 1.0550 1.3694 1.5940 0.092 Uiso 1 1 calc R . . C11 C 1.07759(14) 1.0941(2) 1.61510(18) 0.0527(10) Uani 1 1 d . B . C22 C 0.92621(18) 1.2549(3) 1.6027(2) 0.0706(12) Uani 1 1 d . . . H22 H 0.8935 1.2261 1.6045 0.085 Uiso 1 1 calc R B . C16 C 1.14691(17) 1.2565(3) 1.5148(2) 0.0662(12) Uani 1 1 d . . . H16 H 1.1834 1.2698 1.5172 0.079 Uiso 1 1 calc R B . C5 C 0.98507(19) 1.1684(3) 1.3522(2) 0.0767(14) Uani 1 1 d . B . H5 H 0.9562 1.1470 1.3734 0.092 Uiso 1 1 calc R . . C1 C 1.07559(19) 1.2127(3) 1.3454(2) 0.0703(13) Uani 1 1 d . B . H1 H 1.1093 1.2215 1.3621 0.084 Uiso 1 1 calc R . . C18 C 0.9609(2) 1.3919(3) 1.4422(3) 0.102(2) Uani 1 1 d . . . H18A H 0.9768 1.4393 1.4629 0.122 Uiso 1 1 calc R . . H18B H 0.9232 1.3877 1.4532 0.122 Uiso 1 1 calc R . . C24 C 0.9761(3) 1.3775(3) 1.6188(2) 0.0946(17) Uani 1 1 d . . . H24 H 0.9780 1.4332 1.6319 0.114 Uiso 1 1 calc R B . C4 C 0.9786(2) 1.1859(4) 1.2940(2) 0.0901(16) Uani 1 1 d . . . H4 H 0.9455 1.1745 1.2766 0.108 Uiso 1 1 calc R B . C23 C 0.9293(2) 1.3365(3) 1.6225(2) 0.0834(15) Uani 1 1 d . B . H23 H 0.8992 1.3629 1.6384 0.100 Uiso 1 1 calc R . . C2 C 1.0685(2) 1.2305(3) 1.2870(2) 0.0865(15) Uani 1 1 d . . . H2 H 1.0975 1.2499 1.2652 0.104 Uiso 1 1 calc R B . C3 C 1.0193(3) 1.2194(4) 1.2617(2) 0.0907(17) Uani 1 1 d . B . H3 H 1.0136 1.2344 1.2233 0.109 Uiso 1 1 calc R . . C13 C 1.0843(3) 1.0942(3) 1.7297(2) 0.105(2) Uani 1 1 d . B . H13A H 1.1065 1.1153 1.7611 0.126 Uiso 1 1 calc R A 1 H13B H 1.0476 1.0891 1.7436 0.126 Uiso 1 1 calc R A 1 C12A C 1.1034(6) 1.0135(5) 1.7121(3) 0.081(3) Uiso 0.73(2) 1 d P B 1 H12A H 1.0900 0.9704 1.7384 0.097 Uiso 0.73(2) 1 calc PR B 1 H12B H 1.1425 1.0127 1.7136 0.097 Uiso 0.73(2) 1 calc PR B 1 C12B C 1.0709(15) 1.0046(10) 1.7151(7) 0.065(8) Uiso 0.27(2) 1 d P B 2 H12C H 1.0337 0.9927 1.7252 0.077 Uiso 0.27(2) 1 calc PR B 2 H12D H 1.0939 0.9663 1.7368 0.077 Uiso 0.27(2) 1 calc PR B 2 C19 C 0.9652(3) 1.4065(4) 1.3790(4) 0.156(3) Uani 1 1 d . . . H19A H 0.9480 1.3607 1.3588 0.234 Uiso 1 1 calc R . . H19B H 1.0026 1.4091 1.3682 0.234 Uiso 1 1 calc R . . H19C H 0.9479 1.4591 1.3693 0.234 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 S1 0.0782(8) 0.0509(6) 0.0676(7) 0.0075(6) -0.0023(6) 0.0090(5) S2 0.1054(10) 0.0633(7) 0.0630(7) -0.0078(6) -0.0146(7) -0.0016(7) O2 0.0501(18) 0.0589(17) 0.073(2) 0.0009(14) -0.0002(16) -0.0186(14) O1 0.123(3) 0.0412(17) 0.064(2) 0.0006(14) 0.0122(18) 0.0058(17) O4 0.0436(18) 0.0547(17) 0.101(2) 0.0060(16) -0.0034(16) -0.0020(13) C7 0.056(3) 0.044(2) 0.065(3) 0.0006(19) 0.006(2) -0.003(2) C10 0.042(2) 0.037(2) 0.050(2) -0.0003(18) 0.0040(18) -0.0029(16) C14 0.037(2) 0.040(2) 0.059(3) -0.0010(18) 0.0005(18) -0.0119(17) C21 0.061(3) 0.043(2) 0.056(2) -0.0057(19) 0.005(2) 0.001(2) O3 0.0663(19) 0.0412(16) 0.108(2) 0.0150(16) 0.0002(18) -0.0119(14) C17 0.051(3) 0.048(3) 0.062(3) 0.0049(19) 0.007(2) 0.001(2) C20 0.060(3) 0.031(2) 0.059(3) -0.0039(19) 0.008(2) -0.0005(19) C9 0.060(3) 0.044(2) 0.057(3) 0.001(2) 0.009(2) 0.0068(19) C15 0.042(2) 0.043(2) 0.061(3) 0.0080(19) 0.0056(19) -0.0005(18) N1 0.036(2) 0.076(2) 0.071(3) 0.008(2) 0.001(2) 0.0010(17) C8 0.075(3) 0.051(2) 0.066(3) -0.005(2) 0.004(2) 0.004(2) C6 0.059(3) 0.051(2) 0.062(3) 0.002(2) 0.004(2) 0.004(2) C25 0.084(4) 0.050(3) 0.096(4) -0.011(2) 0.019(3) -0.011(2) C11 0.036(2) 0.054(2) 0.068(3) -0.0025(19) 0.0045(19) 0.0021(18) C22 0.063(3) 0.074(3) 0.075(3) -0.005(3) 0.018(3) 0.011(2) C16 0.041(3) 0.064(3) 0.094(4) 0.011(3) 0.009(3) -0.011(2) C5 0.063(3) 0.095(4) 0.072(3) 0.002(3) -0.002(3) -0.005(3) C1 0.065(3) 0.083(3) 0.063(3) 0.002(3) 0.003(3) 0.009(2) C18 0.069(4) 0.057(3) 0.180(7) 0.016(4) -0.009(4) 0.012(3) C24 0.123(5) 0.048(3) 0.113(4) -0.023(3) 0.034(4) 0.012(3) C4 0.079(4) 0.113(4) 0.079(4) 0.000(3) -0.019(3) 0.003(3) C23 0.085(4) 0.078(4) 0.088(4) -0.008(3) 0.030(3) 0.019(3) C2 0.077(4) 0.108(4) 0.074(4) 0.017(3) 0.010(3) 0.004(3) C3 0.104(5) 0.107(4) 0.061(3) 0.009(3) 0.001(4) 0.026(3) C13 0.157(6) 0.098(4) 0.060(3) 0.010(3) -0.015(3) -0.030(4) C19 0.154(7) 0.103(5) 0.211(10) 0.038(6) -0.070(7) 0.010(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 S1 C11 1.747(4) . ? S1 C12B 1.816(17) . ? S1 C12A 1.840(8) . ? S2 C11 1.750(4) . ? S2 C13 1.768(5) . ? O2 C16 1.360(5) . ? O2 C14 1.465(4) . ? O1 C9 1.231(4) . ? O4 C17 1.344(5) . ? O4 C18 1.478(5) . ? C7 C8 1.509(5) . ? C7 C6 1.515(5) . ? C7 C15 1.530(5) . ? C7 H7 0.9800 . ? C10 C11 1.350(5) . ? C10 C9 1.443(5) . ? C10 C14 1.547(5) . ? C14 C20 1.512(5) . ? C14 C15 1.568(5) . ? C21 C22 1.368(5) . ? C21 C20 1.387(5) . ? C21 H21 0.9300 . ? O3 C17 1.193(4) . ? C17 C15 1.544(5) . ? C20 C25 1.384(5) . ? C9 C8 1.494(6) . ? C15 N1 1.486(5) . ? N1 C16 1.250(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C6 C1 1.374(5) . ? C6 C5 1.383(6) . ? C25 C24 1.406(6) . ? C25 H25 0.9300 . ? C22 C23 1.367(6) . ? C22 H22 0.9300 . ? C16 H16 0.9300 . ? C5 C4 1.384(7) . ? C5 H5 0.9300 . ? C1 C2 1.392(7) . ? C1 H1 0.9300 . ? C18 C19 1.484(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C24 C23 1.330(7) . ? C24 H24 0.9300 . ? C4 C3 1.363(7) . ? C4 H4 0.9300 . ? C23 H23 0.9300 . ? C2 C3 1.366(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C13 C12A 1.417(8) . ? C13 C12B 1.489(19) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C11 S1 C12B 99.3(5) . . ? C11 S1 C12A 95.5(3) . . ? C12B S1 C12A 25.9(8) . . ? C11 S2 C13 98.1(2) . . ? C16 O2 C14 103.8(3) . . ? C17 O4 C18 116.1(3) . . ? C8 C7 C6 112.5(3) . . ? C8 C7 C15 108.9(3) . . ? C6 C7 C15 115.1(3) . . ? C8 C7 H7 106.6 . . ? C6 C7 H7 106.6 . . ? C15 C7 H7 106.6 . . ? C11 C10 C9 118.4(3) . . ? C11 C10 C14 119.4(3) . . ? C9 C10 C14 122.2(3) . . ? O2 C14 C20 109.0(3) . . ? O2 C14 C10 106.9(3) . . ? C20 C14 C10 113.3(3) . . ? O2 C14 C15 100.9(3) . . ? C20 C14 C15 113.5(3) . . ? C10 C14 C15 112.2(3) . . ? C22 C21 C20 120.8(4) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? O3 C17 O4 124.2(3) . . ? O3 C17 C15 124.8(4) . . ? O4 C17 C15 111.0(3) . . ? C25 C20 C21 118.1(4) . . ? C25 C20 C14 122.2(3) . . ? C21 C20 C14 119.6(3) . . ? O1 C9 C10 121.5(4) . . ? O1 C9 C8 118.7(4) . . ? C10 C9 C8 119.7(3) . . ? N1 C15 C7 114.4(3) . . ? N1 C15 C17 105.3(3) . . ? C7 C15 C17 110.1(3) . . ? N1 C15 C14 103.4(3) . . ? C7 C15 C14 113.4(3) . . ? C17 C15 C14 109.8(3) . . ? C16 N1 C15 104.2(4) . . ? C9 C8 C7 113.3(3) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C1 C6 C5 117.2(4) . . ? C1 C6 C7 123.4(4) . . ? C5 C6 C7 119.3(4) . . ? C20 C25 C24 118.8(4) . . ? C20 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C10 C11 S1 124.6(3) . . ? C10 C11 S2 122.5(3) . . ? S1 C11 S2 112.9(2) . . ? C23 C22 C21 121.1(4) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? N1 C16 O2 121.2(4) . . ? N1 C16 H16 119.4 . . ? O2 C16 H16 119.4 . . ? C6 C5 C4 120.6(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C6 C1 C2 121.7(4) . . ? C6 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? O4 C18 C19 109.4(5) . . ? O4 C18 H18A 109.8 . . ? C19 C18 H18A 109.8 . . ? O4 C18 H18B 109.8 . . ? C19 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? C23 C24 C25 122.3(5) . . ? C23 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? C3 C4 C5 121.7(5) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C24 C23 C22 118.8(4) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C3 C2 C1 120.3(5) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 118.3(5) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C12A C13 C12B 32.7(9) . . ? C12A C13 S2 110.6(5) . . ? C12B C13 S2 116.6(7) . . ? C12A C13 H13A 109.5 . . ? C12B C13 H13A 128.4 . . ? S2 C13 H13A 109.5 . . ? C12A C13 H13B 109.5 . . ? C12B C13 H13B 77.7 . . ? S2 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C12A S1 111.0(6) . . ? C13 C12A H12A 109.4 . . ? S1 C12A H12A 109.4 . . ? C13 C12A H12B 109.4 . . ? S1 C12A H12B 109.4 . . ? H12A C12A H12B 108.0 . . ? C13 C12B S1 108.8(12) . . ? C13 C12B H12C 109.9 . . ? S1 C12B H12C 109.9 . . ? C13 C12B H12D 109.9 . . ? S1 C12B H12D 109.9 . . ? H12C C12B H12D 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C16 O2 C14 C20 -141.4(3) . . . . ? C16 O2 C14 C10 95.8(3) . . . . ? C16 O2 C14 C15 -21.7(3) . . . . ? C11 C10 C14 O2 61.2(4) . . . . ? C9 C10 C14 O2 -118.2(4) . . . . ? C11 C10 C14 C20 -59.0(4) . . . . ? C9 C10 C14 C20 121.6(4) . . . . ? C11 C10 C14 C15 170.9(3) . . . . ? C9 C10 C14 C15 -8.5(5) . . . . ? C18 O4 C17 O3 2.5(6) . . . . ? C18 O4 C17 C15 -177.6(4) . . . . ? C22 C21 C20 C25 2.1(6) . . . . ? C22 C21 C20 C14 -174.3(4) . . . . ? O2 C14 C20 C25 24.7(5) . . . . ? C10 C14 C20 C25 143.6(4) . . . . ? C15 C14 C20 C25 -86.9(4) . . . . ? O2 C14 C20 C21 -159.1(3) . . . . ? C10 C14 C20 C21 -40.1(5) . . . . ? C15 C14 C20 C21 89.4(4) . . . . ? C11 C10 C9 O1 4.8(6) . . . . ? C14 C10 C9 O1 -175.8(4) . . . . ? C11 C10 C9 C8 -173.5(4) . . . . ? C14 C10 C9 C8 6.0(5) . . . . ? C8 C7 C15 N1 57.6(4) . . . . ? C6 C7 C15 N1 -69.8(4) . . . . ? C8 C7 C15 C17 176.0(3) . . . . ? C6 C7 C15 C17 48.6(4) . . . . ? C8 C7 C15 C14 -60.6(4) . . . . ? C6 C7 C15 C14 172.0(3) . . . . ? O3 C17 C15 N1 -18.8(5) . . . . ? O4 C17 C15 N1 161.3(3) . . . . ? O3 C17 C15 C7 -142.6(4) . . . . ? O4 C17 C15 C7 37.5(4) . . . . ? O3 C17 C15 C14 91.9(5) . . . . ? O4 C17 C15 C14 -88.0(4) . . . . ? O2 C14 C15 N1 24.9(3) . . . . ? C20 C14 C15 N1 141.4(3) . . . . ? C10 C14 C15 N1 -88.6(3) . . . . ? O2 C14 C15 C7 149.3(3) . . . . ? C20 C14 C15 C7 -94.2(4) . . . . ? C10 C14 C15 C7 35.8(4) . . . . ? O2 C14 C15 C17 -87.0(3) . . . . ? C20 C14 C15 C17 29.4(4) . . . . ? C10 C14 C15 C17 159.5(3) . . . . ? C7 C15 N1 C16 -142.8(3) . . . . ? C17 C15 N1 C16 96.2(4) . . . . ? C14 C15 N1 C16 -19.0(4) . . . . ? O1 C9 C8 C7 151.0(4) . . . . ? C10 C9 C8 C7 -30.7(5) . . . . ? C6 C7 C8 C9 -174.2(4) . . . . ? C15 C7 C8 C9 57.0(4) . . . . ? C8 C7 C6 C1 -78.1(5) . . . . ? C15 C7 C6 C1 47.5(5) . . . . ? C8 C7 C6 C5 100.6(5) . . . . ? C15 C7 C6 C5 -133.9(4) . . . . ? C21 C20 C25 C24 -1.6(6) . . . . ? C14 C20 C25 C24 174.7(4) . . . . ? C9 C10 C11 S1 -3.1(5) . . . . ? C14 C10 C11 S1 177.5(3) . . . . ? C9 C10 C11 S2 174.3(3) . . . . ? C14 C10 C11 S2 -5.2(5) . . . . ? C12B S1 C11 C10 -165.0(12) . . . . ? C12A S1 C11 C10 169.2(6) . . . . ? C12B S1 C11 S2 17.5(12) . . . . ? C12A S1 C11 S2 -8.4(5) . . . . ? C13 S2 C11 C10 173.6(4) . . . . ? C13 S2 C11 S1 -8.8(3) . . . . ? C20 C21 C22 C23 -1.9(7) . . . . ? C15 N1 C16 O2 5.4(5) . . . . ? C14 O2 C16 N1 11.8(5) . . . . ? C1 C6 C5 C4 -1.1(7) . . . . ? C7 C6 C5 C4 -179.9(4) . . . . ? C5 C6 C1 C2 1.5(6) . . . . ? C7 C6 C1 C2 -179.9(4) . . . . ? C17 O4 C18 C19 83.4(6) . . . . ? C20 C25 C24 C23 0.9(8) . . . . ? C6 C5 C4 C3 -1.8(8) . . . . ? C25 C24 C23 C22 -0.7(8) . . . . ? C21 C22 C23 C24 1.2(7) . . . . ? C6 C1 C2 C3 1.1(7) . . . . ? C5 C4 C3 C2 4.3(9) . . . . ? C1 C2 C3 C4 -3.9(8) . . . . ? C11 S2 C13 C12A 28.9(7) . . . . ? C11 S2 C13 C12B -6.2(16) . . . . ? C12B C13 C12A S1 69.3(14) . . . . ? S2 C13 C12A S1 -38.0(10) . . . . ? C11 S1 C12A C13 28.5(9) . . . . ? C12B S1 C12A C13 -71.3(14) . . . . ? C12A C13 C12B S1 -69.2(17) . . . . ? S2 C13 C12B S1 18(2) . . . . ? C11 S1 C12B C13 -20.8(19) . . . . ? C12A S1 C12B C13 62.8(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.178 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.033 # Attachment '6b.cif' data_11 _database_code_depnum_ccdc_archive 'CCDC 761982' #TrackingRef '6b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O5' _chemical_formula_weight 303.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.5750(8) _cell_length_b 12.0480(12) _cell_length_c 16.6840(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1522.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 152 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9814 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 8852 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.75 _reflns_number_total 3225 _reflns_number_gt 2175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0755P)^2^+0.3051P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(3) _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 -0.6(19) _refine_ls_number_reflns 3225 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.5161(3) 0.92931(18) 0.20057(14) 0.0663(6) Uani 1 1 d . . . N1 N 0.4478(3) 1.03235(19) 0.09164(15) 0.0514(6) Uani 1 1 d . . . C10 C 0.1975(4) 0.9096(2) 0.04814(16) 0.0463(7) Uani 1 1 d . . . H10 H 0.0688 0.9174 0.0502 0.056 Uiso 1 1 calc R . . C7 C 0.3335(4) 0.9006(3) 0.18372(17) 0.0511(7) Uani 1 1 d . . . H7 H 0.2584 0.9093 0.2312 0.061 Uiso 1 1 calc R . . O2 O -0.0039(3) 1.0486(2) 0.15666(16) 0.0852(8) Uani 1 1 d . . . C9 C 0.2794(4) 0.9819(2) 0.11553(16) 0.0460(7) Uani 1 1 d . . . C6 C 0.3178(3) 0.7869(2) 0.14812(16) 0.0465(7) Uani 1 1 d . . . O3 O 0.2260(4) 1.1628(2) 0.16526(17) 0.0876(9) Uani 1 1 d . . . C1 C 0.2451(3) 0.7924(2) 0.07211(15) 0.0445(6) Uani 1 1 d . . . O5 O 0.1121(4) 1.1080(2) -0.02071(16) 0.0808(8) Uani 1 1 d . . . C11 C 0.2598(4) 0.9383(2) -0.03664(17) 0.0559(7) Uani 1 1 d . . . H11A H 0.3861 0.9254 -0.0393 0.067 Uiso 1 1 calc R . . H11B H 0.2043 0.8869 -0.0737 0.067 Uiso 1 1 calc R . . C5 C 0.3637(4) 0.6865(3) 0.18231(19) 0.0596(8) Uani 1 1 d . . . H5 H 0.4120 0.6839 0.2335 0.072 Uiso 1 1 calc R . . C2 C 0.2196(4) 0.6959(2) 0.02878(19) 0.0557(7) Uani 1 1 d . . . H2 H 0.1726 0.6982 -0.0227 0.067 Uiso 1 1 calc R . . C8 C 0.5609(4) 0.9982(3) 0.1414(2) 0.0592(8) Uani 1 1 d . . . H8 H 0.6775 1.0215 0.1367 0.071 Uiso 1 1 calc R . . C14 C 0.1492(4) 1.0674(3) 0.1470(2) 0.0591(8) Uani 1 1 d . . . O4 O 0.2914(5) 1.0911(2) -0.12480(17) 0.1062(10) Uani 1 1 d . . . C4 C 0.3369(4) 0.5908(3) 0.1395(2) 0.0669(9) Uani 1 1 d . . . H4 H 0.3672 0.5227 0.1618 0.080 Uiso 1 1 calc R . . C12 C 0.2245(5) 1.0534(3) -0.0653(2) 0.0622(8) Uani 1 1 d . . . C3 C 0.2654(4) 0.5952(3) 0.0637(2) 0.0663(9) Uani 1 1 d . . . H3 H 0.2475 0.5297 0.0354 0.080 Uiso 1 1 calc R . . C13 C 0.0691(8) 1.2208(3) -0.0460(3) 0.1182(18) Uani 1 1 d . . . H13A H -0.0128 1.2530 -0.0087 0.177 Uiso 1 1 calc R . . H13B H 0.0169 1.2190 -0.0984 0.177 Uiso 1 1 calc R . . H13C H 0.1749 1.2647 -0.0474 0.177 Uiso 1 1 calc R . . C15 C 0.1180(7) 1.2529(5) 0.2016(3) 0.1200(19) Uani 1 1 d . . . H15A H 0.1596 1.3243 0.1826 0.144 Uiso 1 1 calc R . . H15B H -0.0043 1.2445 0.1854 0.144 Uiso 1 1 calc R . . C16 C 0.1298(6) 1.2487(5) 0.2823(4) 0.137(2) Uani 1 1 d . . . H16A H 0.0577 1.3061 0.3053 0.205 Uiso 1 1 calc R . . H16B H 0.2504 1.2596 0.2982 0.205 Uiso 1 1 calc R . . H16C H 0.0898 1.1776 0.3009 0.205 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 0.0548(13) 0.0727(14) 0.0715(15) -0.0025(12) -0.0226(11) -0.0083(11) N1 0.0390(13) 0.0509(13) 0.0642(15) -0.0051(12) 0.0066(12) -0.0066(11) C10 0.0385(14) 0.0520(16) 0.0485(16) 0.0041(13) -0.0034(11) -0.0034(13) C7 0.0441(16) 0.0621(19) 0.0471(17) -0.0045(13) -0.0007(12) -0.0045(14) O2 0.0445(13) 0.108(2) 0.103(2) -0.0190(15) 0.0129(13) 0.0054(13) C9 0.0385(14) 0.0501(16) 0.0495(15) 0.0014(12) 0.0031(12) -0.0028(12) C6 0.0375(14) 0.0553(17) 0.0466(15) 0.0060(14) 0.0004(11) -0.0050(12) O3 0.0677(15) 0.0735(17) 0.122(2) -0.0391(15) 0.0050(15) 0.0122(14) C1 0.0342(13) 0.0512(15) 0.0482(15) 0.0013(13) -0.0020(12) -0.0061(12) O5 0.0827(19) 0.0695(16) 0.0901(18) 0.0273(14) 0.0018(15) 0.0174(13) C11 0.0568(18) 0.0650(18) 0.0460(15) 0.0061(13) -0.0017(14) -0.0023(16) C5 0.0511(17) 0.068(2) 0.0598(19) 0.0170(16) -0.0093(14) -0.0036(15) C2 0.0493(16) 0.0546(17) 0.0632(18) -0.0009(15) -0.0070(14) -0.0066(15) C8 0.0418(16) 0.0548(18) 0.081(2) -0.0172(18) -0.0012(16) -0.0042(14) C14 0.0441(17) 0.070(2) 0.0631(19) -0.0094(17) 0.0031(14) 0.0095(15) O4 0.143(3) 0.101(2) 0.0747(18) 0.0384(15) 0.0103(18) -0.008(2) C4 0.0561(19) 0.0563(19) 0.088(3) 0.0181(19) -0.0029(18) -0.0012(16) C12 0.066(2) 0.070(2) 0.0508(17) 0.0137(16) -0.0121(16) -0.0086(18) C3 0.0583(19) 0.0539(18) 0.087(2) -0.0014(17) -0.0033(18) -0.0070(16) C13 0.125(4) 0.080(3) 0.149(4) 0.044(3) -0.009(3) 0.030(3) C15 0.116(4) 0.129(4) 0.115(4) -0.034(3) -0.006(3) 0.056(3) C16 0.076(3) 0.196(6) 0.138(5) -0.056(5) 0.020(3) 0.016(3) _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 C8 1.334(4) . ? O1 C7 1.453(3) . ? N1 C8 1.262(4) . ? N1 C9 1.468(4) . ? C10 C1 1.511(4) . ? C10 C11 1.531(4) . ? C10 C9 1.552(4) . ? C10 H10 0.9800 . ? C7 C6 1.498(4) . ? C7 C9 1.556(4) . ? C7 H7 0.9800 . ? O2 C14 1.192(4) . ? C9 C14 1.519(4) . ? C6 C5 1.382(4) . ? C6 C1 1.384(4) . ? O3 C14 1.325(4) . ? O3 C15 1.487(5) . ? C1 C2 1.384(4) . ? O5 C12 1.308(4) . ? O5 C13 1.460(4) . ? C11 C12 1.492(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C5 C4 1.371(5) . ? C5 H5 0.9300 . ? C2 C3 1.389(4) . ? C2 H2 0.9300 . ? C8 H8 0.9300 . ? O4 C12 1.203(4) . ? C4 C3 1.377(5) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 C16 1.352(7) . ? 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 C8 O1 C7 104.3(2) . . ? C8 N1 C9 106.0(2) . . ? C1 C10 C11 112.4(2) . . ? C1 C10 C9 103.7(2) . . ? C11 C10 C9 114.8(2) . . ? C1 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C9 C10 H10 108.5 . . ? O1 C7 C6 111.7(2) . . ? O1 C7 C9 104.0(2) . . ? C6 C7 C9 105.4(2) . . ? O1 C7 H7 111.8 . . ? C6 C7 H7 111.8 . . ? C9 C7 H7 111.8 . . ? N1 C9 C14 112.2(2) . . ? N1 C9 C10 112.5(2) . . ? C14 C9 C10 111.8(2) . . ? N1 C9 C7 103.3(2) . . ? C14 C9 C7 110.2(2) . . ? C10 C9 C7 106.4(2) . . ? C5 C6 C1 121.3(3) . . ? C5 C6 C7 128.1(3) . . ? C1 C6 C7 110.5(2) . . ? C14 O3 C15 119.0(3) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 C10 127.9(2) . . ? C6 C1 C10 112.5(2) . . ? C12 O5 C13 116.7(3) . . ? C12 C11 C10 116.8(3) . . ? C12 C11 H11A 108.1 . . ? C10 C11 H11A 108.1 . . ? C12 C11 H11B 108.1 . . ? C10 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? N1 C8 O1 121.1(3) . . ? N1 C8 H8 119.4 . . ? O1 C8 H8 119.4 . . ? O2 C14 O3 124.1(3) . . ? O2 C14 C9 123.3(3) . . ? O3 C14 C9 112.5(3) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? O4 C12 O5 123.6(4) . . ? O4 C12 C11 122.7(4) . . ? O5 C12 C11 113.7(3) . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C15 O3 110.0(5) . . ? C16 C15 H15A 109.7 . . ? O3 C15 H15A 109.7 . . ? C16 C15 H15B 109.7 . . ? O3 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? 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 C8 O1 C7 C6 103.1(3) . . . . ? C8 O1 C7 C9 -10.0(3) . . . . ? C8 N1 C9 C14 111.8(3) . . . . ? C8 N1 C9 C10 -121.1(3) . . . . ? C8 N1 C9 C7 -6.9(3) . . . . ? C1 C10 C9 N1 100.3(2) . . . . ? C11 C10 C9 N1 -22.8(3) . . . . ? C1 C10 C9 C14 -132.4(2) . . . . ? C11 C10 C9 C14 104.5(3) . . . . ? C1 C10 C9 C7 -12.2(3) . . . . ? C11 C10 C9 C7 -135.2(3) . . . . ? O1 C7 C9 N1 10.3(3) . . . . ? C6 C7 C9 N1 -107.3(2) . . . . ? O1 C7 C9 C14 -109.7(3) . . . . ? C6 C7 C9 C14 132.7(2) . . . . ? O1 C7 C9 C10 129.0(2) . . . . ? C6 C7 C9 C10 11.4(3) . . . . ? O1 C7 C6 C5 62.4(4) . . . . ? C9 C7 C6 C5 174.7(3) . . . . ? O1 C7 C6 C1 -118.5(3) . . . . ? C9 C7 C6 C1 -6.1(3) . . . . ? C5 C6 C1 C2 -0.8(4) . . . . ? C7 C6 C1 C2 180.0(3) . . . . ? C5 C6 C1 C10 177.4(3) . . . . ? C7 C6 C1 C10 -1.9(3) . . . . ? C11 C10 C1 C2 -48.4(4) . . . . ? C9 C10 C1 C2 -173.0(3) . . . . ? C11 C10 C1 C6 133.6(3) . . . . ? C9 C10 C1 C6 9.0(3) . . . . ? C1 C10 C11 C12 -178.1(2) . . . . ? C9 C10 C11 C12 -59.8(3) . . . . ? C1 C6 C5 C4 0.3(4) . . . . ? C7 C6 C5 C4 179.4(3) . . . . ? C6 C1 C2 C3 1.0(4) . . . . ? C10 C1 C2 C3 -176.8(3) . . . . ? C9 N1 C8 O1 0.4(4) . . . . ? C7 O1 C8 N1 6.7(4) . . . . ? C15 O3 C14 O2 1.1(6) . . . . ? C15 O3 C14 C9 -176.3(3) . . . . ? N1 C9 C14 O2 166.7(3) . . . . ? C10 C9 C14 O2 39.2(4) . . . . ? C7 C9 C14 O2 -78.8(4) . . . . ? N1 C9 C14 O3 -15.8(4) . . . . ? C10 C9 C14 O3 -143.3(3) . . . . ? C7 C9 C14 O3 98.7(3) . . . . ? C6 C5 C4 C3 0.0(5) . . . . ? C13 O5 C12 O4 -0.3(6) . . . . ? C13 O5 C12 C11 -179.1(3) . . . . ? C10 C11 C12 O4 167.6(3) . . . . ? C10 C11 C12 O5 -13.6(4) . . . . ? C5 C4 C3 C2 0.3(5) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C14 O3 C15 C16 94.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.037