# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address F.Bouillere ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; D.Feytens ;Universit\'e Pierre et Marie Curie Paris 6, CNRS, UMR 7613, 4 place Jussieu, Paris, F-75005. ; D.Gori ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; R.Guillot ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; C.Kouklovsky ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; E.Miclet ;Universit\'e Pierre et Marie Curie Paris 6, CNRS, UMR 7613, 4 place Jussieu, Paris, F-75005. ; ; V.Alezra ; ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; _publ_contact_author_address ;Univ. Paris-Sud, CNRS, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, Orsay, F-91405. ; _publ_contact_author_email valerie.alezra@u-psud.fr _publ_contact_author_name 'Valerie Alezra' data_901GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 798420' _database_code_CSD 'CCDC 798420' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H30 N2 O5' _chemical_formula_sum 'C18 H30 N2 O5' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 354.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7347(3) _cell_length_b 17.0484(9) _cell_length_c 10.2113(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.0450(10) _cell_angle_gamma 90.00 _cell_volume 992.78(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 6917 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 39.92 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9763 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19619 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 40.60 _reflns_number_total 9587 _reflns_number_gt 8202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0610P)^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 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 0.1(3) _refine_ls_number_reflns 9587 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C1 C 0.53707(17) 0.09231(6) 0.70439(10) 0.02014(17) Uani 1 1 d . . . H1A H 0.4081 0.0872 0.6370 0.030 Uiso 1 1 calc R . . H1B H 0.5994 0.0413 0.7276 0.030 Uiso 1 1 calc R . . H1C H 0.6571 0.1241 0.6724 0.030 Uiso 1 1 calc R . . C2 C 0.65772(17) 0.14534(6) 0.92901(11) 0.02115(17) Uani 1 1 d . . . H2A H 0.7715 0.1779 0.8928 0.032 Uiso 1 1 calc R . . H2B H 0.7285 0.0962 0.9563 0.032 Uiso 1 1 calc R . . H2C H 0.6029 0.1711 1.0035 0.032 Uiso 1 1 calc R . . C3 C 0.26128(16) 0.08393(6) 0.88220(10) 0.01982(17) Uani 1 1 d . . . H3A H 0.2123 0.1111 0.9569 0.030 Uiso 1 1 calc R . . H3B H 0.3210 0.0332 0.9091 0.030 Uiso 1 1 calc R . . H3C H 0.1299 0.0779 0.8165 0.030 Uiso 1 1 calc R . . C4 C 0.45248(15) 0.13081(5) 0.82518(9) 0.01571(14) Uani 1 1 d . . . C5 C 0.19351(14) 0.22370(5) 0.69732(8) 0.01380(13) Uani 1 1 d . . . C6 C -0.00965(14) 0.32902(5) 0.57358(8) 0.01255(13) Uani 1 1 d . . . H6 H 0.0050 0.3006 0.4914 0.015 Uiso 1 1 calc R . . C7 C 0.02296(13) 0.41783(5) 0.55449(8) 0.01210(12) Uani 1 1 d . . . H7 H 0.1851 0.4329 0.5835 0.015 Uiso 1 1 calc R . . C8 C -0.26005(14) 0.32266(5) 0.61266(9) 0.01408(13) Uani 1 1 d . . . H8A H -0.3716 0.3136 0.5360 0.017 Uiso 1 1 calc R . . H8B H -0.2722 0.2804 0.6751 0.017 Uiso 1 1 calc R . . C9 C -0.30248(14) 0.40111(5) 0.67452(8) 0.01376(13) Uani 1 1 d . . . C10 C -0.04252(15) 0.44333(5) 0.41198(8) 0.01463(14) Uani 1 1 d . . . H10A H -0.2030 0.4282 0.3839 0.018 Uiso 1 1 calc R . . H10B H -0.0315 0.5000 0.4056 0.018 Uiso 1 1 calc R . . C11 C 0.12033(14) 0.40546(5) 0.32367(8) 0.01401(14) Uani 1 1 d . . . C12 C 0.12507(16) 0.35241(6) 0.09991(9) 0.01770(16) Uani 1 1 d . . . C13 C 0.2049(3) 0.27109(7) 0.14325(14) 0.0333(3) Uani 1 1 d . . . H13A H 0.3295 0.2750 0.2135 0.050 Uiso 1 1 calc R . . H13B H 0.2601 0.2437 0.0704 0.050 Uiso 1 1 calc R . . H13C H 0.0759 0.2429 0.1734 0.050 Uiso 1 1 calc R . . C14 C 0.32481(19) 0.40300(7) 0.06265(10) 0.0258(2) Uani 1 1 d . . . H14A H 0.2705 0.4558 0.0475 0.039 Uiso 1 1 calc R . . H14B H 0.3806 0.3828 -0.0161 0.039 Uiso 1 1 calc R . . H14C H 0.4500 0.4025 0.1329 0.039 Uiso 1 1 calc R . . C15 C -0.0701(2) 0.34940(9) -0.01212(11) 0.0308(3) Uani 1 1 d . . . H15A H -0.2012 0.3211 0.0156 0.046 Uiso 1 1 calc R . . H15B H -0.0151 0.3233 -0.0863 0.046 Uiso 1 1 calc R . . H15C H -0.1179 0.4018 -0.0366 0.046 Uiso 1 1 calc R . . C16 C -0.13383(16) 0.53480(6) 0.67523(9) 0.01820(16) Uani 1 1 d . . . H16A H -0.2365 0.5440 0.7433 0.022 Uiso 1 1 calc R . . H16B H -0.1939 0.5646 0.5980 0.022 Uiso 1 1 calc R . . C17 C 0.10775(19) 0.56296(6) 0.72215(10) 0.02173(18) Uani 1 1 d . . . H17 H 0.1896 0.5374 0.7932 0.026 Uiso 1 1 calc R . . C18 C 0.2108(2) 0.62219(7) 0.66809(13) 0.0284(2) Uani 1 1 d . . . H18A H 0.1329 0.6488 0.5970 0.034 Uiso 1 1 calc R . . H18B H 0.3614 0.6373 0.7011 0.034 Uiso 1 1 calc R . . N1 N 0.16359(12) 0.30165(4) 0.67772(7) 0.01329(12) Uani 1 1 d . . . H1 H 0.2462 0.3347 0.7264 0.016 Uiso 1 1 calc R . . N2 N -0.13591(13) 0.45152(4) 0.64261(7) 0.01399(12) Uani 1 1 d . . . O1 O 0.37048(11) 0.21115(4) 0.79365(7) 0.01564(12) Uani 1 1 d . . . O2 O 0.07439(12) 0.17320(4) 0.63829(7) 0.01943(13) Uani 1 1 d . . . O3 O -0.46270(11) 0.41741(4) 0.74153(6) 0.01762(12) Uani 1 1 d . . . O4 O 0.32400(12) 0.39078(5) 0.35746(7) 0.02096(14) Uani 1 1 d . . . O5 O 0.00734(11) 0.39087(4) 0.20536(6) 0.01703(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0188(4) 0.0190(4) 0.0239(4) -0.0018(3) 0.0083(3) 0.0018(3) C2 0.0170(3) 0.0214(4) 0.0245(4) 0.0029(3) -0.0002(3) 0.0040(3) C3 0.0174(3) 0.0173(4) 0.0262(4) 0.0045(3) 0.0090(3) 0.0020(3) C4 0.0137(3) 0.0143(3) 0.0196(4) 0.0024(3) 0.0043(3) 0.0030(3) C5 0.0119(3) 0.0156(3) 0.0144(3) 0.0015(3) 0.0037(2) 0.0011(3) C6 0.0116(3) 0.0153(3) 0.0110(3) 0.0005(3) 0.0028(2) 0.0007(3) C7 0.0121(3) 0.0146(3) 0.0101(3) 0.0002(3) 0.0036(2) 0.0004(3) C8 0.0110(3) 0.0167(3) 0.0148(3) 0.0000(3) 0.0029(2) -0.0009(3) C9 0.0111(3) 0.0186(4) 0.0117(3) 0.0008(3) 0.0018(2) 0.0010(3) C10 0.0147(3) 0.0185(4) 0.0112(3) 0.0018(3) 0.0039(2) 0.0038(3) C11 0.0157(3) 0.0159(3) 0.0113(3) 0.0016(3) 0.0055(2) 0.0003(3) C12 0.0190(3) 0.0205(4) 0.0150(4) -0.0046(3) 0.0080(3) -0.0007(3) C13 0.0477(7) 0.0190(5) 0.0356(6) -0.0035(4) 0.0153(5) 0.0046(5) C14 0.0276(4) 0.0329(5) 0.0190(4) -0.0031(4) 0.0120(3) -0.0086(4) C15 0.0243(4) 0.0486(7) 0.0197(5) -0.0149(5) 0.0034(3) -0.0008(5) C16 0.0191(4) 0.0167(4) 0.0195(4) -0.0040(3) 0.0053(3) 0.0018(3) C17 0.0256(4) 0.0199(4) 0.0186(4) -0.0034(3) -0.0026(3) -0.0003(3) C18 0.0254(5) 0.0240(5) 0.0356(6) -0.0026(4) 0.0029(4) -0.0043(4) N1 0.0114(3) 0.0147(3) 0.0139(3) 0.0006(2) 0.0015(2) 0.0005(2) N2 0.0143(3) 0.0157(3) 0.0128(3) -0.0018(2) 0.0051(2) -0.0004(2) O1 0.0147(2) 0.0132(3) 0.0185(3) 0.0016(2) -0.0003(2) 0.0014(2) O2 0.0171(3) 0.0177(3) 0.0231(3) -0.0005(2) 0.0000(2) -0.0018(2) O3 0.0126(2) 0.0252(3) 0.0158(3) -0.0012(2) 0.00539(19) 0.0015(2) O4 0.0144(2) 0.0326(4) 0.0167(3) 0.0015(3) 0.0052(2) 0.0045(3) O5 0.0165(2) 0.0231(3) 0.0123(2) -0.0035(2) 0.00508(19) 0.0021(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 C1 C4 1.5210(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.5192(13) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.5214(13) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 O1 1.4726(11) . ? C5 O2 1.2184(11) . ? C5 N1 1.3522(11) . ? C5 O1 1.3539(10) . ? C6 N1 1.4536(11) . ? C6 C8 1.5342(11) . ? C6 C7 1.5406(12) . ? C6 H6 0.9800 . ? C7 N2 1.4637(10) . ? C7 C10 1.5272(11) . ? C7 H7 0.9800 . ? C8 C9 1.5098(13) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O3 1.2337(10) . ? C9 N2 1.3501(11) . ? C10 C11 1.5099(12) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O4 1.2087(11) . ? C11 O5 1.3327(10) . ? C12 O5 1.4827(11) . ? C12 C13 1.5116(16) . ? C12 C14 1.5142(14) . ? C12 C15 1.5149(14) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N2 1.4580(12) . ? C16 C17 1.4965(15) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.3201(17) . ? C17 H17 0.9300 . ? C18 H18A 0.9300 . ? C18 H18B 0.9300 . ? N1 H1 0.8600 . ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C2 101.95(7) . . ? O1 C4 C1 110.24(7) . . ? C2 C4 C1 110.27(8) . . ? O1 C4 C3 110.23(7) . . ? C2 C4 C3 110.80(8) . . ? C1 C4 C3 112.82(8) . . ? O2 C5 N1 124.43(8) . . ? O2 C5 O1 125.88(8) . . ? N1 C5 O1 109.67(7) . . ? N1 C6 C8 111.92(7) . . ? N1 C6 C7 108.99(7) . . ? C8 C6 C7 103.40(6) . . ? N1 C6 H6 110.8 . . ? C8 C6 H6 110.8 . . ? C7 C6 H6 110.8 . . ? N2 C7 C10 111.57(7) . . ? N2 C7 C6 102.49(6) . . ? C10 C7 C6 112.30(7) . . ? N2 C7 H7 110.1 . . ? C10 C7 H7 110.1 . . ? C6 C7 H7 110.1 . . ? C9 C8 C6 104.05(7) . . ? C9 C8 H8A 110.9 . . ? C6 C8 H8A 110.9 . . ? C9 C8 H8B 110.9 . . ? C6 C8 H8B 110.9 . . ? H8A C8 H8B 109.0 . . ? O3 C9 N2 125.29(9) . . ? O3 C9 C8 126.43(8) . . ? N2 C9 C8 108.28(7) . . ? C11 C10 C7 109.99(7) . . ? C11 C10 H10A 109.7 . . ? C7 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C7 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O4 C11 O5 125.67(8) . . ? O4 C11 C10 123.91(8) . . ? O5 C11 C10 110.42(7) . . ? O5 C12 C13 109.89(8) . . ? O5 C12 C14 110.18(8) . . ? C13 C12 C14 112.47(9) . . ? O5 C12 C15 101.92(7) . . ? C13 C12 C15 111.53(10) . . ? C14 C12 C15 110.36(9) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 111.75(8) . . ? N2 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N2 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 123.49(10) . . ? C18 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? C5 N1 C6 119.34(7) . . ? C5 N1 H1 120.3 . . ? C6 N1 H1 120.3 . . ? C9 N2 C16 123.62(7) . . ? C9 N2 C7 113.61(7) . . ? C16 N2 C7 122.14(7) . . ? C5 O1 C4 120.23(7) . . ? C11 O5 C12 121.72(7) . . ? 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 N1 C6 C7 N2 -91.71(7) . . . . ? C8 C6 C7 N2 27.49(8) . . . . ? N1 C6 C7 C10 148.44(6) . . . . ? C8 C6 C7 C10 -92.36(8) . . . . ? N1 C6 C8 C9 90.99(8) . . . . ? C7 C6 C8 C9 -26.17(8) . . . . ? C6 C8 C9 O3 -165.70(8) . . . . ? C6 C8 C9 N2 15.11(9) . . . . ? N2 C7 C10 C11 -178.24(7) . . . . ? C6 C7 C10 C11 -63.83(9) . . . . ? C7 C10 C11 O4 -32.88(12) . . . . ? C7 C10 C11 O5 146.99(8) . . . . ? N2 C16 C17 C18 124.44(11) . . . . ? O2 C5 N1 C6 -4.63(12) . . . . ? O1 C5 N1 C6 176.79(7) . . . . ? C8 C6 N1 C5 76.90(9) . . . . ? C7 C6 N1 C5 -169.35(7) . . . . ? O3 C9 N2 C16 -4.95(14) . . . . ? C8 C9 N2 C16 174.24(8) . . . . ? O3 C9 N2 C7 -176.01(8) . . . . ? C8 C9 N2 C7 3.19(9) . . . . ? C17 C16 N2 C9 138.18(9) . . . . ? C17 C16 N2 C7 -51.50(11) . . . . ? C10 C7 N2 C9 100.46(8) . . . . ? C6 C7 N2 C9 -19.90(9) . . . . ? C10 C7 N2 C16 -70.75(10) . . . . ? C6 C7 N2 C16 168.90(7) . . . . ? O2 C5 O1 C4 7.15(12) . . . . ? N1 C5 O1 C4 -174.29(7) . . . . ? C2 C4 O1 C5 176.19(7) . . . . ? C1 C4 O1 C5 59.10(10) . . . . ? C3 C4 O1 C5 -66.11(10) . . . . ? O4 C11 O5 C12 1.01(14) . . . . ? C10 C11 O5 C12 -178.87(8) . . . . ? C13 C12 O5 C11 61.93(12) . . . . ? C14 C12 O5 C11 -62.53(11) . . . . ? C15 C12 O5 C11 -179.69(9) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.379 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.052