# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sl0338 _database_code_depnum_ccdc_archive 'CCDC 704059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N O5' _chemical_formula_sum 'C18 H21 N O5' _chemical_formula_weight 331.36 _chemical_absolute_configuration ; 1130 Friedel pairs were averaged for the refinement ; 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0302(3) _cell_length_b 8.0096(3) _cell_length_c 12.1640(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.7370(10) _cell_angle_gamma 90.00 _cell_volume 828.12(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3208 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The absolute structure was assigned from the KNOWN configuration of the starting material. The -OH hydrogen atom was located and its position was refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4767 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2025 _reflns_number_gt 1838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.2182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(13) _refine_ls_number_reflns 2025 _refine_ls_number_parameters 220 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 1.3058(2) 0.6255(3) 0.57244(16) 0.0488(5) Uani 1 1 d . . . O2 O 0.87076(18) 0.5450(2) 0.31164(14) 0.0340(4) Uani 1 1 d . . . O3 O 1.03462(17) 0.3445(2) 0.12564(14) 0.0326(4) Uani 1 1 d . . . O4 O 0.8523(3) 0.4336(3) -0.16511(17) 0.0556(6) Uani 1 1 d . . . O5 O 0.8057(2) 0.6231(2) -0.04612(18) 0.0442(5) Uani 1 1 d D . . H5A H 0.861(3) 0.691(4) -0.086(3) 0.053 Uiso 1 1 d D . . N1 N 0.9799(2) 0.4483(3) 0.27792(16) 0.0282(4) Uani 1 1 d . . . C1 C 1.3206(3) 0.4614(4) 0.5447(2) 0.0384(6) Uani 1 1 d . . . C2 C 1.4242(3) 0.3599(5) 0.6297(2) 0.0518(8) Uani 1 1 d . . . H2 H 1.4857 0.4059 0.7029 0.062 Uiso 1 1 calc R . . C3 C 1.4371(3) 0.1937(5) 0.6075(3) 0.0551(8) Uani 1 1 d . . . H3 H 1.5068 0.1248 0.6658 0.066 Uiso 1 1 calc R . . C4 C 1.3494(3) 0.1254(4) 0.5008(3) 0.0498(7) Uani 1 1 d . . . H4 H 1.3566 0.0096 0.4865 0.060 Uiso 1 1 calc R . . C5 C 1.2513(3) 0.2273(4) 0.4153(2) 0.0397(6) Uani 1 1 d . . . H5 H 1.1934 0.1811 0.3413 0.048 Uiso 1 1 calc R . . C6 C 1.2357(2) 0.3971(4) 0.43582(19) 0.0324(5) Uani 1 1 d . . . C7 C 1.1401(3) 0.5122(3) 0.33913(19) 0.0294(5) Uani 1 1 d . . . H7 H 1.1957 0.5249 0.2811 0.035 Uiso 1 1 calc R . . C8 C 1.1110(3) 0.6873(3) 0.3807(2) 0.0365(5) Uani 1 1 d . . . H8 H 1.1727 0.7737 0.3553 0.044 Uiso 1 1 calc R . . C9 C 1.1511(3) 0.6906(4) 0.5121(2) 0.0424(6) Uani 1 1 d . . . H9A H 1.1449 0.8069 0.5376 0.051 Uiso 1 1 calc R . . H9B H 1.0725 0.6236 0.5333 0.051 Uiso 1 1 calc R . . C10 C 0.9353(3) 0.7115(3) 0.3184(2) 0.0411(6) Uani 1 1 d . . . H10A H 0.8901 0.7865 0.3635 0.049 Uiso 1 1 calc R . . H10B H 0.9144 0.7589 0.2394 0.049 Uiso 1 1 calc R . . C11 C 0.9336(2) 0.3931(3) 0.16543(18) 0.0263(4) Uani 1 1 d . . . C12 C 0.7581(2) 0.3845(3) 0.09973(18) 0.0258(4) Uani 1 1 d . . . H12 H 0.7118 0.4959 0.1064 0.031 Uiso 1 1 calc R . . C13 C 0.6804(3) 0.2536(3) 0.1554(2) 0.0373(6) Uani 1 1 d . . . H13A H 0.7131 0.2734 0.2406 0.045 Uiso 1 1 calc R . . H13B H 0.5646 0.2656 0.1224 0.045 Uiso 1 1 calc R . . C14 C 0.7260(3) 0.0775(4) 0.1333(3) 0.0500(8) Uani 1 1 d . . . H14A H 0.8413 0.0634 0.1693 0.060 Uiso 1 1 calc R . . H14B H 0.6744 -0.0039 0.1699 0.060 Uiso 1 1 calc R . . C15 C 0.6770(3) 0.0437(4) 0.0037(3) 0.0558(8) Uani 1 1 d . . . H15A H 0.5611 0.0522 -0.0313 0.067 Uiso 1 1 calc R . . H15B H 0.7077 -0.0714 -0.0090 0.067 Uiso 1 1 calc R . . C16 C 0.7524(3) 0.1659(3) -0.0568(3) 0.0416(6) Uani 1 1 d . . . H16A H 0.7097 0.1469 -0.1422 0.050 Uiso 1 1 calc R . . H16B H 0.8673 0.1455 -0.0306 0.050 Uiso 1 1 calc R . . C17 C 0.7223(2) 0.3475(3) -0.03063(19) 0.0293(5) Uani 1 1 d . . . H17 H 0.6067 0.3658 -0.0688 0.035 Uiso 1 1 calc R . . C18 C 0.8017(3) 0.4692(4) -0.0881(2) 0.0347(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0445(10) 0.0650(14) 0.0328(9) -0.0159(10) 0.0077(8) -0.0053(10) O2 0.0338(8) 0.0387(9) 0.0337(9) -0.0046(8) 0.0170(7) 0.0037(8) O3 0.0278(7) 0.0407(10) 0.0304(8) -0.0087(7) 0.0114(6) 0.0007(8) O4 0.0632(12) 0.0763(16) 0.0365(10) -0.0070(10) 0.0290(9) -0.0071(12) O5 0.0532(11) 0.0357(10) 0.0558(12) 0.0068(9) 0.0343(9) -0.0019(9) N1 0.0255(9) 0.0349(10) 0.0260(9) -0.0029(8) 0.0111(7) 0.0028(8) C1 0.0309(11) 0.0572(17) 0.0285(11) -0.0052(12) 0.0119(9) -0.0028(12) C2 0.0317(12) 0.093(3) 0.0265(12) 0.0005(15) 0.0047(9) 0.0027(16) C3 0.0363(14) 0.079(2) 0.0496(17) 0.0155(16) 0.0135(12) 0.0179(16) C4 0.0380(14) 0.0568(18) 0.0544(17) 0.0088(16) 0.0153(13) 0.0122(14) C5 0.0316(12) 0.0479(16) 0.0382(13) -0.0006(12) 0.0101(10) 0.0053(12) C6 0.0248(10) 0.0470(14) 0.0265(10) -0.0009(10) 0.0101(9) -0.0022(11) C7 0.0292(10) 0.0367(12) 0.0230(10) -0.0039(10) 0.0098(8) -0.0045(10) C8 0.0444(13) 0.0346(13) 0.0328(12) -0.0047(10) 0.0161(11) -0.0054(11) C9 0.0512(15) 0.0431(15) 0.0345(13) -0.0113(12) 0.0165(11) -0.0023(13) C10 0.0502(15) 0.0353(13) 0.0388(13) -0.0020(11) 0.0163(11) 0.0079(12) C11 0.0268(10) 0.0265(10) 0.0255(10) 0.0016(9) 0.0089(8) 0.0029(9) C12 0.0257(10) 0.0261(10) 0.0256(10) 0.0026(9) 0.0088(8) 0.0023(9) C13 0.0305(11) 0.0433(15) 0.0378(13) 0.0123(11) 0.0108(10) -0.0019(11) C14 0.0360(13) 0.0344(15) 0.077(2) 0.0167(14) 0.0151(13) -0.0027(12) C15 0.0388(14) 0.0324(14) 0.094(2) -0.0120(16) 0.0192(15) -0.0068(13) C16 0.0320(12) 0.0401(15) 0.0493(15) -0.0183(12) 0.0095(11) -0.0030(11) C17 0.0244(10) 0.0332(12) 0.0284(11) -0.0014(9) 0.0066(8) -0.0014(10) C18 0.0289(11) 0.0488(15) 0.0249(11) 0.0038(10) 0.0071(9) 0.0022(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.375(4) . ? O1 C9 1.439(3) . ? O2 N1 1.419(2) . ? O2 C10 1.446(3) . ? O3 C11 1.232(3) . ? O4 C18 1.207(3) . ? O5 C18 1.330(3) . ? O5 H5A 0.975(18) . ? N1 C11 1.362(3) . ? N1 C7 1.477(3) . ? C1 C6 1.386(3) . ? C1 C2 1.398(4) . ? C2 C3 1.371(6) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C6 C7 1.514(3) . ? C7 C8 1.543(3) . ? C7 H7 1.0000 . ? C8 C9 1.515(4) . ? C8 C10 1.522(4) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(3) . ? C12 C17 1.537(3) . ? C12 C13 1.540(3) . ? C12 H12 1.0000 . ? C13 C14 1.519(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.511(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.517(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.533(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(3) . ? C17 H17 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 112.3(2) . . ? N1 O2 C10 102.34(17) . . ? C18 O5 H5A 106(2) . . ? C11 N1 O2 117.38(17) . . ? C11 N1 C7 122.33(17) . . ? O2 N1 C7 108.83(17) . . ? O1 C1 C6 121.5(2) . . ? O1 C1 C2 118.1(2) . . ? C6 C1 C2 120.4(3) . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C7 120.1(2) . . ? C5 C6 C7 121.3(2) . . ? N1 C7 C6 112.7(2) . . ? N1 C7 C8 103.55(19) . . ? C6 C7 C8 114.47(19) . . ? N1 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C9 C8 C10 111.1(2) . . ? C9 C8 C7 110.8(2) . . ? C10 C8 C7 102.5(2) . . ? C9 C8 H8 110.7 . . ? C10 C8 H8 110.7 . . ? C7 C8 H8 110.7 . . ? O1 C9 C8 112.1(2) . . ? O1 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O2 C10 C8 104.1(2) . . ? O2 C10 H10A 110.9 . . ? C8 C10 H10A 110.9 . . ? O2 C10 H10B 110.9 . . ? C8 C10 H10B 110.9 . . ? H10A C10 H10B 109.0 . . ? O3 C11 N1 118.72(18) . . ? O3 C11 C12 124.02(19) . . ? N1 C11 C12 117.11(17) . . ? C11 C12 C17 111.77(17) . . ? C11 C12 C13 110.46(18) . . ? C17 C12 C13 110.71(19) . . ? C11 C12 H12 107.9 . . ? C17 C12 H12 107.9 . . ? C13 C12 H12 107.9 . . ? C14 C13 C12 111.3(2) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 110.4(2) . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.7(2) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 111.8(2) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 111.7(2) . . ? C18 C17 C12 112.63(19) . . ? C16 C17 C12 114.1(2) . . ? C18 C17 H17 105.9 . . ? C16 C17 H17 105.9 . . ? C12 C17 H17 105.9 . . ? O4 C18 O5 123.3(3) . . ? O4 C18 C17 124.7(3) . . ? O5 C18 C17 112.0(2) . . ? 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 C10 O2 N1 C11 -106.0(2) . . . . ? C10 O2 N1 C7 38.4(2) . . . . ? C9 O1 C1 C6 30.7(3) . . . . ? C9 O1 C1 C2 -149.3(2) . . . . ? O1 C1 C2 C3 177.0(3) . . . . ? C6 C1 C2 C3 -2.9(4) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 1.7(4) . . . . ? C3 C4 C5 C6 -1.8(4) . . . . ? O1 C1 C6 C5 -177.2(2) . . . . ? C2 C1 C6 C5 2.7(4) . . . . ? O1 C1 C6 C7 8.0(4) . . . . ? C2 C1 C6 C7 -172.0(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C4 C5 C6 C7 174.4(2) . . . . ? C11 N1 C7 C6 -110.9(2) . . . . ? O2 N1 C7 C6 106.8(2) . . . . ? C11 N1 C7 C8 124.9(2) . . . . ? O2 N1 C7 C8 -17.4(2) . . . . ? C1 C6 C7 N1 -133.4(2) . . . . ? C5 C6 C7 N1 51.9(3) . . . . ? C1 C6 C7 C8 -15.4(3) . . . . ? C5 C6 C7 C8 169.9(2) . . . . ? N1 C7 C8 C9 109.2(2) . . . . ? C6 C7 C8 C9 -13.8(3) . . . . ? N1 C7 C8 C10 -9.4(2) . . . . ? C6 C7 C8 C10 -132.4(2) . . . . ? C1 O1 C9 C8 -61.4(3) . . . . ? C10 C8 C9 O1 164.8(2) . . . . ? C7 C8 C9 O1 51.5(3) . . . . ? N1 O2 C10 C8 -43.6(2) . . . . ? C9 C8 C10 O2 -86.0(3) . . . . ? C7 C8 C10 O2 32.4(2) . . . . ? O2 N1 C11 O3 163.0(2) . . . . ? C7 N1 C11 O3 23.7(3) . . . . ? O2 N1 C11 C12 -21.2(3) . . . . ? C7 N1 C11 C12 -160.5(2) . . . . ? O3 C11 C12 C17 -13.4(3) . . . . ? N1 C11 C12 C17 171.0(2) . . . . ? O3 C11 C12 C13 110.3(3) . . . . ? N1 C11 C12 C13 -65.2(3) . . . . ? C11 C12 C13 C14 -70.6(3) . . . . ? C17 C12 C13 C14 53.7(3) . . . . ? C12 C13 C14 C15 -59.2(3) . . . . ? C13 C14 C15 C16 58.9(3) . . . . ? C14 C15 C16 C17 -53.5(3) . . . . ? C15 C16 C17 C18 178.3(2) . . . . ? C15 C16 C17 C12 49.1(3) . . . . ? C11 C12 C17 C18 -54.1(3) . . . . ? C13 C12 C17 C18 -177.73(19) . . . . ? C11 C12 C17 C16 74.6(2) . . . . ? C13 C12 C17 C16 -49.0(2) . . . . ? C16 C17 C18 O4 15.5(3) . . . . ? C12 C17 C18 O4 145.4(2) . . . . ? C16 C17 C18 O5 -166.3(2) . . . . ? C12 C17 C18 O5 -36.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.160 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.046 data_sl0428 _database_code_depnum_ccdc_archive 'CCDC 704060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O5' _chemical_formula_sum 'C18 H23 N O5' _chemical_formula_weight 333.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6843(2) _cell_length_b 10.9358(3) _cell_length_c 10.2015(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.974(2) _cell_angle_gamma 90.00 _cell_volume 841.60(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3991 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; 1250 Friedel pairs averaged for the refinement. The absolute structure was assigned from the known configuration of the starting material. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5141 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2004 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1001P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(11) _refine_ls_number_reflns 2004 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.349 _refine_ls_restrained_S_all 1.348 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 O1A O 0.0897(2) 0.51919(15) 0.60784(14) 0.0283(4) Uani 1 1 d . . . O1 O 0.1498(2) 0.66687(16) 0.91612(15) 0.0314(4) Uani 1 1 d . . . C1 C 0.1180(2) 0.5854(2) 0.83310(18) 0.0217(4) Uani 1 1 d . . . O2 O -0.1719(2) 0.5175(2) 1.21343(16) 0.0420(5) Uani 1 1 d . . . C2 C 0.0416(3) 0.46104(19) 0.85821(18) 0.0223(4) Uani 1 1 d . . . H2 H -0.0567 0.4415 0.7818 0.027 Uiso 1 1 calc R . . O3 O -0.4216(3) 0.5981(2) 1.09515(18) 0.0391(4) Uani 1 1 d . . . C3 C 0.1850(3) 0.3629(2) 0.8653(3) 0.0343(5) Uani 1 1 d . . . H3X H 0.2280 0.3611 0.7808 0.051 Uiso 1 1 calc R . . H3Y H 0.1352 0.2829 0.8810 0.051 Uiso 1 1 calc R . . H3Z H 0.2836 0.3819 0.9385 0.051 Uiso 1 1 calc R . . C4 C -0.0337(2) 0.4622(2) 0.98682(19) 0.0244(4) Uani 1 1 d . . . H4X H -0.0460 0.3768 1.0160 0.029 Uiso 1 1 calc R . . H4Y H 0.0515 0.5040 1.0576 0.029 Uiso 1 1 calc R . . C5 C -0.2134(2) 0.5258(2) 0.97160(18) 0.0236(4) Uani 1 1 d . . . H5 H -0.2037 0.6078 0.9302 0.028 Uiso 1 1 calc R . . C6 C -0.3607(3) 0.4539(3) 0.8815(3) 0.0424(7) Uani 1 1 d . . . H6X H -0.4714 0.5007 0.8691 0.064 Uiso 1 1 calc R . . H6Y H -0.3773 0.3751 0.9232 0.064 Uiso 1 1 calc R . . H6Z H -0.3276 0.4399 0.7946 0.064 Uiso 1 1 calc R . . C7 C -0.2628(3) 0.5449(2) 1.1071(2) 0.0272(4) Uani 1 1 d . . . C8 C -0.4859(5) 0.6208(3) 1.2173(3) 0.0504(8) Uani 1 1 d . . . H8X H -0.6093 0.6484 1.1957 0.076 Uiso 1 1 calc R . . H8Y H -0.4129 0.6840 1.2693 0.076 Uiso 1 1 calc R . . H8Z H -0.4789 0.5452 1.2697 0.076 Uiso 1 1 calc R . . N1A N 0.1688(2) 0.60056(16) 0.71117(16) 0.0231(4) Uani 1 1 d . . . C1A C -0.0436(3) 0.5940(2) 0.5266(2) 0.0317(5) Uani 1 1 d . . . H1AA H -0.1462 0.6071 0.5708 0.038 Uiso 1 1 calc R . . H1AB H -0.0856 0.5563 0.4381 0.038 Uiso 1 1 calc R . . O2A O 0.2810(2) 0.80715(18) 0.41010(16) 0.0350(4) Uani 1 1 d . . . C2A C 0.0532(3) 0.7134(2) 0.5139(2) 0.0267(4) Uani 1 1 d . . . H2A H -0.0321 0.7833 0.4979 0.032 Uiso 1 1 calc R . . C3A C 0.1621(3) 0.7064(3) 0.4047(2) 0.0322(5) Uani 1 1 d . . . H3AA H 0.2307 0.6292 0.4142 0.039 Uiso 1 1 calc R . . H3AB H 0.0815 0.7053 0.3166 0.039 Uiso 1 1 calc R . . C4A C 0.4029(3) 0.8104(2) 0.5280(2) 0.0272(4) Uani 1 1 d . . . C5A C 0.5683(3) 0.8614(2) 0.5237(3) 0.0332(5) Uani 1 1 d . . . H5A H 0.5923 0.8946 0.4429 0.040 Uiso 1 1 calc R . . C6A C 0.6974(3) 0.8630(2) 0.6395(3) 0.0343(5) Uani 1 1 d . . . H6A H 0.8103 0.8979 0.6381 0.041 Uiso 1 1 calc R . . C7A C 0.6618(3) 0.8136(2) 0.7574(3) 0.0355(5) Uani 1 1 d . . . H7A H 0.7519 0.8120 0.8354 0.043 Uiso 1 1 calc R . . C8A C 0.4953(3) 0.7669(2) 0.7611(2) 0.0303(5) Uani 1 1 d . . . H8A H 0.4708 0.7359 0.8427 0.036 Uiso 1 1 calc R . . C9A C 0.3626(3) 0.76479(19) 0.6462(2) 0.0243(4) Uani 1 1 d . . . C10A C 0.1758(3) 0.72447(19) 0.65284(18) 0.0229(4) Uani 1 1 d . . . H10A H 0.1229 0.7845 0.7080 0.027 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 O1A 0.0388(8) 0.0239(7) 0.0234(7) -0.0056(6) 0.0092(6) -0.0026(7) O1 0.0441(9) 0.0269(8) 0.0256(7) -0.0049(6) 0.0128(6) -0.0079(7) C1 0.0214(8) 0.0225(9) 0.0216(8) 0.0021(7) 0.0049(6) 0.0005(7) O2 0.0515(11) 0.0523(12) 0.0235(7) -0.0012(8) 0.0101(6) 0.0009(9) C2 0.0218(9) 0.0216(9) 0.0240(9) 0.0023(7) 0.0056(6) 0.0003(7) O3 0.0382(9) 0.0434(11) 0.0418(9) 0.0001(9) 0.0228(7) 0.0044(8) C3 0.0331(11) 0.0263(11) 0.0469(13) 0.0072(10) 0.0164(10) 0.0086(9) C4 0.0226(9) 0.0262(10) 0.0252(9) 0.0068(8) 0.0066(7) 0.0013(7) C5 0.0222(8) 0.0264(10) 0.0224(8) 0.0008(8) 0.0052(6) -0.0007(7) C6 0.0230(10) 0.0619(19) 0.0414(12) -0.0203(13) 0.0041(8) -0.0041(11) C7 0.0309(10) 0.0243(10) 0.0286(10) -0.0014(8) 0.0108(7) -0.0070(8) C8 0.0645(18) 0.0396(14) 0.0608(17) -0.0052(13) 0.0464(15) -0.0051(13) N1A 0.0290(8) 0.0201(8) 0.0208(8) -0.0015(7) 0.0067(6) -0.0020(6) C1A 0.0308(10) 0.0393(12) 0.0241(9) -0.0022(9) 0.0032(7) -0.0054(9) O2A 0.0410(9) 0.0408(10) 0.0237(7) 0.0100(7) 0.0074(6) -0.0043(8) C2A 0.0270(9) 0.0299(11) 0.0229(9) 0.0041(8) 0.0037(7) 0.0035(8) C3A 0.0359(11) 0.0403(12) 0.0211(9) 0.0012(9) 0.0069(7) -0.0044(10) C4A 0.0316(10) 0.0250(10) 0.0266(10) 0.0031(8) 0.0096(8) 0.0014(8) C5A 0.0373(11) 0.0291(11) 0.0387(12) 0.0028(9) 0.0210(9) 0.0003(9) C6A 0.0296(10) 0.0249(10) 0.0521(14) -0.0027(10) 0.0167(9) -0.0029(9) C7A 0.0335(11) 0.0301(11) 0.0410(12) 0.0005(10) 0.0020(9) -0.0043(9) C8A 0.0369(11) 0.0272(11) 0.0267(10) 0.0028(8) 0.0059(8) -0.0059(8) C9A 0.0296(9) 0.0204(9) 0.0247(9) 0.0010(8) 0.0097(7) 0.0006(7) C10A 0.0288(9) 0.0209(10) 0.0202(8) 0.0008(7) 0.0074(7) -0.0008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A N1A 1.424(2) . ? O1A C1A 1.443(3) . ? O1 C1 1.221(3) . ? C1 N1A 1.383(2) . ? C1 C2 1.522(3) . ? O2 C7 1.211(3) . ? C2 C3 1.530(3) . ? C2 C4 1.531(3) . ? C2 H2 1.0000 . ? O3 C7 1.336(3) . ? O3 C8 1.446(3) . ? C3 H3X 0.9800 . ? C3 H3Y 0.9800 . ? C3 H3Z 0.9800 . ? C4 C5 1.527(3) . ? C4 H4X 0.9900 . ? C4 H4Y 0.9900 . ? C5 C7 1.517(3) . ? C5 C6 1.532(3) . ? C5 H5 1.0000 . ? C6 H6X 0.9800 . ? C6 H6Y 0.9800 . ? C6 H6Z 0.9800 . ? C8 H8X 0.9800 . ? C8 H8Y 0.9800 . ? C8 H8Z 0.9800 . ? N1A C10A 1.485(3) . ? C1A C2A 1.520(3) . ? C1A H1AA 0.9900 . ? C1A H1AB 0.9900 . ? O2A C4A 1.377(3) . ? O2A C3A 1.426(3) . ? C2A C3A 1.517(3) . ? C2A C10A 1.550(3) . ? C2A H2A 1.0000 . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C4A C9A 1.393(3) . ? C4A C5A 1.396(3) . ? C5A C6A 1.390(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.392(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.386(3) . ? C7A H7A 0.9500 . ? C8A C9A 1.399(3) . ? C8A H8A 0.9500 . ? C9A C10A 1.515(3) . ? C10A H10A 1.0000 . ? 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 N1A O1A C1A 103.12(16) . . ? O1 C1 N1A 118.87(19) . . ? O1 C1 C2 124.59(17) . . ? N1A C1 C2 116.26(16) . . ? C1 C2 C3 109.71(16) . . ? C1 C2 C4 110.96(16) . . ? C3 C2 C4 110.57(17) . . ? C1 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C4 C2 H2 108.5 . . ? C7 O3 C8 116.8(2) . . ? C2 C3 H3X 109.5 . . ? C2 C3 H3Y 109.5 . . ? H3X C3 H3Y 109.5 . . ? C2 C3 H3Z 109.5 . . ? H3X C3 H3Z 109.5 . . ? H3Y C3 H3Z 109.5 . . ? C5 C4 C2 113.46(15) . . ? C5 C4 H4X 108.9 . . ? C2 C4 H4X 108.9 . . ? C5 C4 H4Y 108.9 . . ? C2 C4 H4Y 108.9 . . ? H4X C4 H4Y 107.7 . . ? C7 C5 C4 110.41(16) . . ? C7 C5 C6 109.46(18) . . ? C4 C5 C6 112.20(19) . . ? C7 C5 H5 108.2 . . ? C4 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? C5 C6 H6X 109.5 . . ? C5 C6 H6Y 109.5 . . ? H6X C6 H6Y 109.5 . . ? C5 C6 H6Z 109.5 . . ? H6X C6 H6Z 109.5 . . ? H6Y C6 H6Z 109.5 . . ? O2 C7 O3 123.46(19) . . ? O2 C7 C5 125.5(2) . . ? O3 C7 C5 111.07(17) . . ? O3 C8 H8X 109.5 . . ? O3 C8 H8Y 109.5 . . ? H8X C8 H8Y 109.5 . . ? O3 C8 H8Z 109.5 . . ? H8X C8 H8Z 109.5 . . ? H8Y C8 H8Z 109.5 . . ? C1 N1A O1A 115.92(15) . . ? C1 N1A C10A 120.53(16) . . ? O1A N1A C10A 108.46(14) . . ? O1A C1A C2A 103.32(17) . . ? O1A C1A H1AA 111.1 . . ? C2A C1A H1AA 111.1 . . ? O1A C1A H1AB 111.1 . . ? C2A C1A H1AB 111.1 . . ? H1AA C1A H1AB 109.1 . . ? C4A O2A C3A 112.21(17) . . ? C3A C2A C1A 111.5(2) . . ? C3A C2A C10A 110.52(17) . . ? C1A C2A C10A 102.21(16) . . ? C3A C2A H2A 110.8 . . ? C1A C2A H2A 110.8 . . ? C10A C2A H2A 110.8 . . ? O2A C3A C2A 111.8(2) . . ? O2A C3A H3AA 109.2 . . ? C2A C3A H3AA 109.2 . . ? O2A C3A H3AB 109.2 . . ? C2A C3A H3AB 109.2 . . ? H3AA C3A H3AB 107.9 . . ? O2A C4A C9A 121.3(2) . . ? O2A C4A C5A 117.1(2) . . ? C9A C4A C5A 121.6(2) . . ? C6A C5A C4A 119.0(2) . . ? C6A C5A H5A 120.5 . . ? C4A C5A H5A 120.5 . . ? C5A C6A C7A 120.2(2) . . ? C5A C6A H6A 119.9 . . ? C7A C6A H6A 119.9 . . ? C8A C7A C6A 120.1(2) . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C7A C8A C9A 120.8(2) . . ? C7A C8A H8A 119.6 . . ? C9A C8A H8A 119.6 . . ? C4A C9A C8A 118.20(19) . . ? C4A C9A C10A 120.76(18) . . ? C8A C9A C10A 120.82(17) . . ? N1A C10A C9A 113.00(17) . . ? N1A C10A C2A 103.45(16) . . ? C9A C10A C2A 113.46(16) . . ? N1A C10A H10A 108.9 . . ? C9A C10A H10A 108.9 . . ? C2A C10A H10A 108.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -108.1(2) . . . . ? N1A C1 C2 C3 65.7(2) . . . . ? O1 C1 C2 C4 14.4(3) . . . . ? N1A C1 C2 C4 -171.79(16) . . . . ? C1 C2 C4 C5 76.8(2) . . . . ? C3 C2 C4 C5 -161.27(19) . . . . ? C2 C4 C5 C7 -169.18(17) . . . . ? C2 C4 C5 C6 68.4(2) . . . . ? C8 O3 C7 O2 -1.2(4) . . . . ? C8 O3 C7 C5 179.5(2) . . . . ? C4 C5 C7 O2 2.1(3) . . . . ? C6 C5 C7 O2 126.0(3) . . . . ? C4 C5 C7 O3 -178.67(17) . . . . ? C6 C5 C7 O3 -54.7(3) . . . . ? O1 C1 N1A O1A -164.43(19) . . . . ? C2 C1 N1A O1A 21.4(2) . . . . ? O1 C1 N1A C10A -30.4(3) . . . . ? C2 C1 N1A C10A 155.44(17) . . . . ? C1A O1A N1A C1 102.81(19) . . . . ? C1A O1A N1A C10A -36.45(19) . . . . ? N1A O1A C1A C2A 44.80(19) . . . . ? O1A C1A C2A C3A 82.2(2) . . . . ? O1A C1A C2A C10A -35.8(2) . . . . ? C4A O2A C3A C2A 61.9(2) . . . . ? C1A C2A C3A O2A -167.89(17) . . . . ? C10A C2A C3A O2A -54.9(3) . . . . ? C3A O2A C4A C9A -29.7(3) . . . . ? C3A O2A C4A C5A 150.3(2) . . . . ? O2A C4A C5A C6A -177.9(2) . . . . ? C9A C4A C5A C6A 2.1(4) . . . . ? C4A C5A C6A C7A 0.4(4) . . . . ? C5A C6A C7A C8A -2.5(4) . . . . ? C6A C7A C8A C9A 2.1(4) . . . . ? O2A C4A C9A C8A 177.6(2) . . . . ? C5A C4A C9A C8A -2.4(3) . . . . ? O2A C4A C9A C10A -7.7(3) . . . . ? C5A C4A C9A C10A 172.3(2) . . . . ? C7A C8A C9A C4A 0.3(3) . . . . ? C7A C8A C9A C10A -174.4(2) . . . . ? C1 N1A C10A C9A 112.90(19) . . . . ? O1A N1A C10A C9A -110.05(18) . . . . ? C1 N1A C10A C2A -123.99(18) . . . . ? O1A N1A C10A C2A 13.06(18) . . . . ? C4A C9A C10A N1A 129.7(2) . . . . ? C8A C9A C10A N1A -55.8(2) . . . . ? C4A C9A C10A C2A 12.3(3) . . . . ? C8A C9A C10A C2A -173.2(2) . . . . ? C3A C2A C10A N1A -104.9(2) . . . . ? C1A C2A C10A N1A 13.90(19) . . . . ? C3A C2A C10A C9A 17.9(3) . . . . ? C1A C2A C10A C9A 136.71(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.973 _refine_diff_density_min -0.971 _refine_diff_density_rms 0.357 data_sl0521 _database_code_depnum_ccdc_archive 'CCDC 704062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 N1 O2 1+,C10 H15 O4 S1 1-' _chemical_formula_sum 'C20 H27 N O6 S' _chemical_formula_weight 409.49 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' O O 0.0106 0.0060 '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' 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 P2(1)2(1)2(1) 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 6.53530(10) _cell_length_b 9.87590(10) _cell_length_c 30.2519(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1952.52(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17681 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.904 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The absolute structure was determined reliably (Flack parameter -0.02(5)). ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12106 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4392 _reflns_number_gt 4240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.5169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(5) _refine_ls_number_reflns 4392 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 1.10967(5) -0.02226(3) 0.168251(10) 0.01615(8) Uani 1 1 d . . . O1 O 0.7583(2) 0.22906(14) 0.06673(4) 0.0446(4) Uani 1 1 d . . . O2 O 1.32330(15) -0.00462(11) 0.15733(3) 0.0234(2) Uani 1 1 d . . . O3 O 1.05227(16) 0.04097(10) 0.21066(3) 0.0207(2) Uani 1 1 d . . . O4 O 1.04401(16) -0.16445(9) 0.16825(3) 0.0213(2) Uani 1 1 d . . . C1 C 0.9585(2) 0.06540(13) 0.12858(4) 0.0189(3) Uani 1 1 d . . . H1A H 0.8132 0.0454 0.1352 0.023 Uiso 1 1 calc R . . H1B H 0.9786 0.1636 0.1336 0.023 Uiso 1 1 calc R . . C2 C 0.9920(2) 0.03871(14) 0.07944(4) 0.0186(3) Uani 1 1 d . . . C3 C 0.8467(3) 0.13027(17) 0.05316(5) 0.0305(4) Uani 1 1 d . . . C4 C 0.8380(3) 0.07425(19) 0.00628(5) 0.0361(4) Uani 1 1 d . . . H4A H 0.8874 0.1414 -0.0155 0.043 Uiso 1 1 calc R . . H4B H 0.6976 0.0456 -0.0017 0.043 Uiso 1 1 calc R . . C5 C 0.9826(2) -0.04680(16) 0.00950(5) 0.0258(3) Uani 1 1 d . . . H5 H 0.9639 -0.1160 -0.0143 0.031 Uiso 1 1 calc R . . C6 C 1.2005(3) 0.01205(17) 0.01254(5) 0.0282(3) Uani 1 1 d . . . H6A H 1.2239 0.0812 -0.0106 0.034 Uiso 1 1 calc R . . H6B H 1.3050 -0.0600 0.0097 0.034 Uiso 1 1 calc R . . C7 C 1.2047(3) 0.07649(17) 0.05958(5) 0.0263(3) Uani 1 1 d . . . H7A H 1.2218 0.1759 0.0578 0.032 Uiso 1 1 calc R . . H7B H 1.3172 0.0381 0.0776 0.032 Uiso 1 1 calc R . . C8 C 0.9466(2) -0.10109(15) 0.05733(5) 0.0216(3) Uani 1 1 d . . . C9 C 0.7289(3) -0.1516(2) 0.06631(6) 0.0369(4) Uani 1 1 d . . . H9A H 0.6992 -0.2291 0.0471 0.055 Uiso 1 1 calc R . . H9B H 0.6311 -0.0787 0.0602 0.055 Uiso 1 1 calc R . . H9C H 0.7172 -0.1792 0.0973 0.055 Uiso 1 1 calc R . . C10 C 1.0955(3) -0.21637(15) 0.06808(5) 0.0285(3) Uani 1 1 d . . . H10A H 1.0912 -0.2840 0.0444 0.043 Uiso 1 1 calc R . . H10B H 1.0559 -0.2588 0.0961 0.043 Uiso 1 1 calc R . . H10C H 1.2345 -0.1800 0.0706 0.043 Uiso 1 1 calc R . . O1A O 1.33065(15) 0.13291(10) 0.29494(4) 0.0236(2) Uani 1 1 d . . . O2A O 1.60717(17) 0.28886(11) 0.18055(3) 0.0252(2) Uani 1 1 d . . . N1A N 1.19630(18) 0.21969(11) 0.26991(4) 0.0176(2) Uani 1 1 d . . . H1AA H 1.0934 0.2517 0.2878 0.021 Uiso 1 1 calc R . . H1AB H 1.1376 0.1716 0.2472 0.021 Uiso 1 1 calc R . . C1A C 1.5181(2) 0.21003(15) 0.30150(5) 0.0226(3) Uani 1 1 d . . . H1AC H 1.6369 0.1489 0.3054 0.027 Uiso 1 1 calc R . . H1AD H 1.5069 0.2694 0.3278 0.027 Uiso 1 1 calc R . . C2A C 1.5392(2) 0.29313(14) 0.25958(5) 0.0197(3) Uani 1 1 d . . . H2AA H 1.6299 0.3733 0.2645 0.024 Uiso 1 1 calc R . . C3A C 1.6121(2) 0.21040(15) 0.22034(5) 0.0232(3) Uani 1 1 d . . . H3AA H 1.7536 0.1787 0.2258 0.028 Uiso 1 1 calc R . . H3AB H 1.5236 0.1298 0.2169 0.028 Uiso 1 1 calc R . . C4A C 1.4201(2) 0.34448(13) 0.17130(5) 0.0205(3) Uani 1 1 d . . . C5A C 1.3862(3) 0.38442(15) 0.12769(5) 0.0263(3) Uani 1 1 d . . . H5AA H 1.4900 0.3727 0.1060 0.032 Uiso 1 1 calc R . . C6A C 1.1999(3) 0.44125(15) 0.11616(5) 0.0276(3) Uani 1 1 d . . . H6AA H 1.1767 0.4688 0.0865 0.033 Uiso 1 1 calc R . . C7A C 1.0460(3) 0.45842(15) 0.14763(5) 0.0250(3) Uani 1 1 d . . . H7AA H 0.9175 0.4955 0.1393 0.030 Uiso 1 1 calc R . . C8A C 1.0820(2) 0.42101(14) 0.19105(5) 0.0202(3) Uani 1 1 d . . . H8AA H 0.9778 0.4333 0.2126 0.024 Uiso 1 1 calc R . . C9A C 1.2708(2) 0.36510(13) 0.20364(5) 0.0176(3) Uani 1 1 d . . . C10A C 1.3190(2) 0.33743(13) 0.25142(5) 0.0175(3) Uani 1 1 d . . . H10D H 1.2897 0.4205 0.2692 0.021 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 0.01798(15) 0.01534(14) 0.01512(14) 0.00078(11) -0.00060(12) 0.00003(12) O1 0.0660(9) 0.0421(7) 0.0256(6) 0.0025(5) 0.0000(6) 0.0345(7) O2 0.0185(5) 0.0277(5) 0.0240(5) 0.0043(4) -0.0001(4) -0.0005(4) O3 0.0252(5) 0.0204(5) 0.0166(5) -0.0013(4) -0.0013(4) -0.0013(4) O4 0.0288(5) 0.0150(4) 0.0200(5) 0.0004(4) 0.0021(4) -0.0019(4) C1 0.0227(7) 0.0173(6) 0.0169(6) -0.0003(5) -0.0006(5) 0.0037(5) C2 0.0222(7) 0.0182(6) 0.0154(6) -0.0002(5) -0.0017(5) 0.0044(5) C3 0.0396(10) 0.0329(8) 0.0192(7) 0.0018(6) -0.0017(6) 0.0165(8) C4 0.0430(11) 0.0468(10) 0.0187(7) -0.0018(7) -0.0052(7) 0.0200(8) C5 0.0299(8) 0.0313(8) 0.0161(7) -0.0037(6) -0.0014(6) 0.0075(6) C6 0.0325(8) 0.0331(8) 0.0190(7) 0.0011(6) 0.0057(6) 0.0010(7) C7 0.0305(8) 0.0266(7) 0.0219(7) 0.0005(6) 0.0050(6) -0.0046(6) C8 0.0239(7) 0.0228(7) 0.0181(6) -0.0047(5) -0.0006(5) 0.0008(6) C9 0.0285(9) 0.0485(10) 0.0337(9) -0.0122(8) 0.0010(7) -0.0112(8) C10 0.0421(9) 0.0201(7) 0.0235(7) -0.0032(6) 0.0036(7) 0.0058(7) O1A 0.0206(5) 0.0176(5) 0.0325(6) 0.0060(4) -0.0070(4) -0.0018(4) O2A 0.0190(5) 0.0301(5) 0.0266(5) -0.0019(4) 0.0041(4) 0.0050(5) N1A 0.0161(5) 0.0171(5) 0.0195(6) 0.0007(4) -0.0015(4) 0.0009(5) C1A 0.0191(7) 0.0211(6) 0.0276(8) -0.0001(6) -0.0056(6) -0.0020(6) C2A 0.0161(6) 0.0183(6) 0.0248(7) -0.0018(5) -0.0030(5) -0.0016(5) C3A 0.0172(6) 0.0235(7) 0.0289(7) -0.0024(6) -0.0003(6) 0.0025(6) C4A 0.0185(6) 0.0176(6) 0.0255(7) -0.0027(5) 0.0023(6) 0.0004(5) C5A 0.0305(8) 0.0253(7) 0.0231(7) -0.0026(6) 0.0074(7) 0.0012(7) C6A 0.0379(9) 0.0253(7) 0.0196(7) 0.0008(6) 0.0008(6) 0.0044(7) C7A 0.0267(7) 0.0229(7) 0.0252(7) 0.0002(6) -0.0013(6) 0.0056(6) C8A 0.0188(7) 0.0181(6) 0.0236(7) -0.0003(5) 0.0015(5) 0.0016(5) C9A 0.0195(7) 0.0138(6) 0.0195(7) -0.0013(5) 0.0017(5) -0.0003(5) C10A 0.0180(6) 0.0140(6) 0.0203(6) -0.0015(5) 0.0001(5) -0.0021(5) _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 O2 1.4453(10) . ? S1 O4 1.4684(10) . ? S1 O3 1.4752(10) . ? S1 C1 1.7793(14) . ? O1 C3 1.206(2) . ? C1 C2 1.5255(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.533(2) . ? C2 C7 1.560(2) . ? C2 C8 1.563(2) . ? C3 C4 1.523(2) . ? C4 C5 1.527(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.541(2) . ? C5 C8 1.561(2) . ? C5 H5 1.0000 . ? C6 C7 1.559(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.532(2) . ? C8 C10 1.533(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O1A N1A 1.4418(15) . ? O1A C1A 1.4562(17) . ? O2A C4A 1.3689(17) . ? O2A C3A 1.4320(18) . ? N1A C10A 1.5191(17) . ? N1A H1AA 0.9200 . ? N1A H1AB 0.9200 . ? C1A C2A 1.517(2) . ? C1A H1AC 0.9900 . ? C1A H1AD 0.9900 . ? C2A C3A 1.5181(19) . ? C2A C10A 1.5244(19) . ? C2A H2AA 1.0000 . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C4A C5A 1.395(2) . ? C4A C9A 1.397(2) . ? C5A C6A 1.385(2) . ? C5A H5AA 0.9500 . ? C6A C7A 1.395(2) . ? C6A H6AA 0.9500 . ? C7A C8A 1.385(2) . ? C7A H7AA 0.9500 . ? C8A C9A 1.4046(19) . ? C8A H8AA 0.9500 . ? C9A C10A 1.5043(19) . ? C10A H10D 1.0000 . ? 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 O2 S1 O4 113.42(6) . . ? O2 S1 O3 113.17(6) . . ? O4 S1 O3 109.30(6) . . ? O2 S1 C1 108.87(7) . . ? O4 S1 C1 107.64(6) . . ? O3 S1 C1 103.86(6) . . ? C2 C1 S1 119.57(10) . . ? C2 C1 H1A 107.4 . . ? S1 C1 H1A 107.4 . . ? C2 C1 H1B 107.4 . . ? S1 C1 H1B 107.4 . . ? H1A C1 H1B 107.0 . . ? C1 C2 C3 108.32(11) . . ? C1 C2 C7 117.51(12) . . ? C3 C2 C7 102.19(12) . . ? C1 C2 C8 122.85(12) . . ? C3 C2 C8 100.46(11) . . ? C7 C2 C8 102.47(11) . . ? O1 C3 C4 126.36(15) . . ? O1 C3 C2 126.69(14) . . ? C4 C3 C2 106.95(12) . . ? C3 C4 C5 101.65(12) . . ? C3 C4 H4A 111.4 . . ? C5 C4 H4A 111.4 . . ? C3 C4 H4B 111.4 . . ? C5 C4 H4B 111.4 . . ? H4A C4 H4B 109.3 . . ? C4 C5 C6 106.28(14) . . ? C4 C5 C8 103.58(12) . . ? C6 C5 C8 102.33(12) . . ? C4 C5 H5 114.4 . . ? C6 C5 H5 114.4 . . ? C8 C5 H5 114.4 . . ? C5 C6 C7 102.99(12) . . ? C5 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? C5 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? C6 C7 C2 103.78(12) . . ? C6 C7 H7A 111.0 . . ? C2 C7 H7A 111.0 . . ? C6 C7 H7B 111.0 . . ? C2 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C9 C8 C10 108.07(14) . . ? C9 C8 C5 114.60(13) . . ? C10 C8 C5 110.86(12) . . ? C9 C8 C2 112.84(13) . . ? C10 C8 C2 116.42(12) . . ? C5 C8 C2 93.70(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1A O1A C1A 105.84(10) . . ? C4A O2A C3A 114.15(11) . . ? O1A N1A C10A 109.09(10) . . ? O1A N1A H1AA 109.9 . . ? C10A N1A H1AA 109.9 . . ? O1A N1A H1AB 109.9 . . ? C10A N1A H1AB 109.9 . . ? H1AA N1A H1AB 108.3 . . ? O1A C1A C2A 104.21(11) . . ? O1A C1A H1AC 110.9 . . ? C2A C1A H1AC 110.9 . . ? O1A C1A H1AD 110.9 . . ? C2A C1A H1AD 110.9 . . ? H1AC C1A H1AD 108.9 . . ? C1A C2A C3A 113.03(12) . . ? C1A C2A C10A 101.84(11) . . ? C3A C2A C10A 108.92(11) . . ? C1A C2A H2AA 110.9 . . ? C3A C2A H2AA 110.9 . . ? C10A C2A H2AA 110.9 . . ? O2A C3A C2A 111.05(11) . . ? O2A C3A H3AA 109.4 . . ? C2A C3A H3AA 109.4 . . ? O2A C3A H3AB 109.4 . . ? C2A C3A H3AB 109.4 . . ? H3AA C3A H3AB 108.0 . . ? O2A C4A C5A 116.67(13) . . ? O2A C4A C9A 122.64(13) . . ? C5A C4A C9A 120.66(13) . . ? C6A C5A C4A 119.51(14) . . ? C6A C5A H5AA 120.2 . . ? C4A C5A H5AA 120.2 . . ? C5A C6A C7A 120.74(14) . . ? C5A C6A H6AA 119.6 . . ? C7A C6A H6AA 119.6 . . ? C8A C7A C6A 119.49(15) . . ? C8A C7A H7AA 120.3 . . ? C6A C7A H7AA 120.3 . . ? C7A C8A C9A 120.75(14) . . ? C7A C8A H8AA 119.6 . . ? C9A C8A H8AA 119.6 . . ? C4A C9A C8A 118.78(13) . . ? C4A C9A C10A 120.02(12) . . ? C8A C9A C10A 121.03(12) . . ? C9A C10A N1A 112.50(11) . . ? C9A C10A C2A 113.91(11) . . ? N1A C10A C2A 102.64(10) . . ? C9A C10A H10D 109.2 . . ? N1A C10A H10D 109.2 . . ? C2A C10A H10D 109.2 . . ? 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 O2 S1 C1 C2 52.56(13) . . . . ? O4 S1 C1 C2 -70.78(12) . . . . ? O3 S1 C1 C2 173.40(11) . . . . ? S1 C1 C2 C3 -178.34(11) . . . . ? S1 C1 C2 C7 -63.30(16) . . . . ? S1 C1 C2 C8 65.46(16) . . . . ? C1 C2 C3 O1 17.0(2) . . . . ? C7 C2 C3 O1 -107.7(2) . . . . ? C8 C2 C3 O1 146.94(19) . . . . ? C1 C2 C3 C4 -164.01(14) . . . . ? C7 C2 C3 C4 71.28(16) . . . . ? C8 C2 C3 C4 -34.05(16) . . . . ? O1 C3 C4 C5 178.76(19) . . . . ? C2 C3 C4 C5 -0.26(18) . . . . ? C3 C4 C5 C6 -72.44(16) . . . . ? C3 C4 C5 C8 34.98(17) . . . . ? C4 C5 C6 C7 70.42(14) . . . . ? C8 C5 C6 C7 -37.89(15) . . . . ? C5 C6 C7 C2 3.58(15) . . . . ? C1 C2 C7 C6 169.65(12) . . . . ? C3 C2 C7 C6 -71.98(14) . . . . ? C8 C2 C7 C6 31.79(14) . . . . ? C4 C5 C8 C9 62.64(17) . . . . ? C6 C5 C8 C9 173.01(13) . . . . ? C4 C5 C8 C10 -174.70(14) . . . . ? C6 C5 C8 C10 -64.34(15) . . . . ? C4 C5 C8 C2 -54.58(14) . . . . ? C6 C5 C8 C2 55.78(13) . . . . ? C1 C2 C8 C9 53.50(18) . . . . ? C3 C2 C8 C9 -66.48(15) . . . . ? C7 C2 C8 C9 -171.60(13) . . . . ? C1 C2 C8 C10 -72.31(17) . . . . ? C3 C2 C8 C10 167.71(13) . . . . ? C7 C2 C8 C10 62.59(15) . . . . ? C1 C2 C8 C5 172.18(13) . . . . ? C3 C2 C8 C5 52.20(13) . . . . ? C7 C2 C8 C5 -52.92(12) . . . . ? C1A O1A N1A C10A 13.65(14) . . . . ? N1A O1A C1A C2A -34.07(13) . . . . ? O1A C1A C2A C3A -75.74(14) . . . . ? O1A C1A C2A C10A 40.95(13) . . . . ? C4A O2A C3A C2A -55.40(16) . . . . ? C1A C2A C3A O2A 173.31(12) . . . . ? C10A C2A C3A O2A 60.90(15) . . . . ? C3A O2A C4A C5A -160.40(12) . . . . ? C3A O2A C4A C9A 21.56(18) . . . . ? O2A C4A C5A C6A 179.91(13) . . . . ? C9A C4A C5A C6A -2.0(2) . . . . ? C4A C5A C6A C7A -0.2(2) . . . . ? C5A C6A C7A C8A 1.5(2) . . . . ? C6A C7A C8A C9A -0.5(2) . . . . ? O2A C4A C9A C8A -179.08(12) . . . . ? C5A C4A C9A C8A 3.0(2) . . . . ? O2A C4A C9A C10A 5.5(2) . . . . ? C5A C4A C9A C10A -172.48(12) . . . . ? C7A C8A C9A C4A -1.7(2) . . . . ? C7A C8A C9A C10A 173.69(13) . . . . ? C4A C9A C10A N1A -113.86(14) . . . . ? C8A C9A C10A N1A 70.81(16) . . . . ? C4A C9A C10A C2A 2.42(17) . . . . ? C8A C9A C10A C2A -172.92(12) . . . . ? O1A N1A C10A C9A 134.77(11) . . . . ? O1A N1A C10A C2A 11.92(13) . . . . ? C1A C2A C10A C9A -153.33(11) . . . . ? C3A C2A C10A C9A -33.70(15) . . . . ? C1A C2A C10A N1A -31.43(13) . . . . ? C3A C2A C10A N1A 88.19(13) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.232 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.038