# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_cd211492 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H29 N O7' _chemical_formula_weight 431.47 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2542(9) _cell_length_b 26.236(3) _cell_length_c 10.2531(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.029(2) _cell_angle_gamma 90.00 _cell_volume 2154.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1308 _cell_measurement_theta_min 5.139 _cell_measurement_theta_max 40.559 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.313 _exptl_crystal_size_mid 0.269 _exptl_crystal_size_min 0.037 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.66858 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11005 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3990 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0955P)^2^+0.6358P] 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_number_reflns 3990 _refine_ls_number_parameters 303 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.1330 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2123 _refine_ls_wR_factor_gt 0.1864 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.007 _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 N1 N 0.1679(4) 0.19003(13) 0.6093(3) 0.0393(8) Uani 1 1 d . . . O1 O -0.1052(4) 0.19127(13) 0.6209(3) 0.0523(8) Uani 1 1 d . . . O2 O 0.0159(5) 0.03328(15) 0.6668(3) 0.0732(11) Uani 1 1 d . . . O3 O 0.1240(4) 0.10060(12) 0.7887(3) 0.0510(8) Uani 1 1 d . . . O4 O 0.1383(3) 0.19323(11) 0.1771(2) 0.0405(7) Uani 1 1 d . . . O5 O 0.3796(4) 0.16531(14) 0.1417(3) 0.0589(9) Uani 1 1 d . . . O6 O -0.2428(4) 0.06154(15) 0.0196(3) 0.0659(11) Uani 1 1 d . A . C1 C 0.0171(5) 0.16958(17) 0.6012(4) 0.0389(10) Uani 1 1 d . . . C2 C 0.0201(5) 0.11355(16) 0.5543(3) 0.0365(10) Uani 1 1 d . . . C3 C -0.1511(5) 0.09915(19) 0.4632(4) 0.0450(11) Uani 1 1 d . . . H3A H -0.1441 0.0646 0.4311 0.054 Uiso 1 1 calc R . . H3B H -0.2325 0.0991 0.5174 0.054 Uiso 1 1 calc R . . C4 C -0.2162(5) 0.1339(2) 0.3410(4) 0.0501(12) Uani 1 1 d . . . H4A H -0.3371 0.1349 0.3222 0.060 Uiso 1 1 calc R . . H4B H -0.1755 0.1682 0.3642 0.060 Uiso 1 1 calc R . . C5 C -0.1657(5) 0.11763(18) 0.2128(4) 0.0425(11) Uani 1 1 d . . . H5 H -0.1748 0.1476 0.1542 0.051 Uiso 1 1 calc R . . C6 C 0.0157(5) 0.09914(17) 0.2440(4) 0.0380(10) Uani 1 1 d . . . H6A H 0.0207 0.0644 0.2774 0.046 Uiso 1 1 calc R . . H6B H 0.0538 0.0989 0.1616 0.046 Uiso 1 1 calc R . . C7 C 0.1315(5) 0.13217(16) 0.3467(4) 0.0348(9) Uani 1 1 d . . . C8 C 0.1798(4) 0.11360(16) 0.4923(4) 0.0348(9) Uani 1 1 d . . . C9 C 0.2901(5) 0.15359(16) 0.5824(4) 0.0378(10) Uani 1 1 d . . . H9 H 0.3505 0.1377 0.6667 0.045 Uiso 1 1 calc R . . C10 C 0.4125(5) 0.18036(18) 0.5164(4) 0.0444(11) Uani 1 1 d . . . H10A H 0.4865 0.2022 0.5808 0.053 Uiso 1 1 calc R . . H10B H 0.4797 0.1556 0.4829 0.053 Uiso 1 1 calc R . . C11 C 0.3104(5) 0.21177(17) 0.4015(4) 0.0420(11) Uani 1 1 d . . . H11 H 0.3850 0.2265 0.3503 0.050 Uiso 1 1 calc R . . C12 C 0.1895(5) 0.17628(17) 0.3122(3) 0.0376(10) Uani 1 1 d . . . C13 C 0.1952(6) 0.24488(17) 0.5957(4) 0.0473(11) Uani 1 1 d . . . H13A H 0.2925 0.2558 0.6636 0.057 Uiso 1 1 calc R . . H13B H 0.0992 0.2639 0.6079 0.057 Uiso 1 1 calc R . . C14 C 0.2215(5) 0.25487(18) 0.4567(4) 0.0435(11) Uani 1 1 d . . . C15 C 0.1738(7) 0.2973(2) 0.3910(5) 0.0634(14) Uani 1 1 d . . . H15A H 0.1217 0.3226 0.4295 0.076 Uiso 1 1 calc R . . H15B H 0.1921 0.3021 0.3058 0.076 Uiso 1 1 calc R . . C16 C 0.2684(6) 0.06225(17) 0.5010(4) 0.0492(12) Uani 1 1 d . . . H16A H 0.1906 0.0366 0.4580 0.074 Uiso 1 1 calc R . . H16B H 0.3123 0.0533 0.5936 0.074 Uiso 1 1 calc R . . H16C H 0.3582 0.0645 0.4567 0.074 Uiso 1 1 calc R . . C17 C 0.0518(5) 0.07757(19) 0.6738(4) 0.0426(10) Uani 1 1 d . . . C18 C 0.1560(7) 0.0694(2) 0.9089(4) 0.0662(15) Uani 1 1 d . . . H18A H 0.0526 0.0623 0.9323 0.099 Uiso 1 1 calc R . . H18B H 0.2294 0.0873 0.9814 0.099 Uiso 1 1 calc R . . H18C H 0.2073 0.0380 0.8925 0.099 Uiso 1 1 calc R . . C19 C 0.2503(5) 0.18669(17) 0.1010(4) 0.0393(10) Uani 1 1 d . . . C20 C 0.1890(6) 0.20890(19) -0.0353(4) 0.0503(12) Uani 1 1 d . . . H20A H 0.2620 0.1991 -0.0910 0.075 Uiso 1 1 calc R . . H20B H 0.1870 0.2454 -0.0288 0.075 Uiso 1 1 calc R . . H20C H 0.0783 0.1966 -0.0744 0.075 Uiso 1 1 calc R . . C21 C -0.2864(5) 0.0784(2) 0.1409(4) 0.0515(12) Uani 1 1 d . . . H21A H -0.2862 0.0494 0.1998 0.062 Uiso 1 1 calc R . . H21B H -0.3981 0.0927 0.1183 0.062 Uiso 1 1 calc R . . C22 C -0.3532(6) 0.0498(3) -0.0859(5) 0.0721(17) Uani 1 1 d D . . O7 O -0.4691(12) 0.0832(4) -0.1158(9) 0.101(3) Uani 0.55 1 d PDU A 1 C23 C -0.3068(13) 0.0202(4) -0.1913(9) 0.066(3) Uani 0.65 1 d PU A 1 H23A H -0.3520 0.0360 -0.2768 0.098 Uiso 0.65 1 calc PR A 1 H23B H -0.3505 -0.0137 -0.1919 0.098 Uiso 0.65 1 calc PR A 1 H23C H -0.1873 0.0188 -0.1748 0.098 Uiso 0.65 1 calc PR A 1 O7' O -0.4917(11) 0.0422(4) -0.0761(9) 0.117(4) Uani 0.45 1 d PDU A 2 C23' C -0.307(3) 0.0504(9) -0.213(2) 0.078(6) Uani 0.35 1 d PU A 2 H23D H -0.3897 0.0326 -0.2788 0.118 Uiso 0.35 1 calc PR A 2 H23E H -0.2007 0.0339 -0.2025 0.118 Uiso 0.35 1 calc PR A 2 H23F H -0.2992 0.0850 -0.2408 0.118 Uiso 0.35 1 calc PR A 2 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 N1 0.051(2) 0.035(2) 0.0326(17) -0.0026(15) 0.0118(14) -0.0009(17) O1 0.0524(18) 0.058(2) 0.0522(18) -0.0025(15) 0.0224(14) 0.0096(16) O2 0.123(3) 0.049(2) 0.0456(19) -0.0004(17) 0.0170(18) -0.029(2) O3 0.075(2) 0.044(2) 0.0308(15) -0.0012(13) 0.0059(13) -0.0031(16) O4 0.0385(15) 0.049(2) 0.0334(14) 0.0022(13) 0.0079(11) -0.0014(13) O5 0.0526(19) 0.076(3) 0.0492(18) 0.0081(16) 0.0146(15) 0.0186(18) O6 0.0443(18) 0.107(3) 0.0420(17) -0.0283(18) 0.0025(14) -0.0125(18) C1 0.045(2) 0.047(3) 0.0256(19) -0.0001(18) 0.0091(17) 0.003(2) C2 0.043(2) 0.039(3) 0.0281(18) -0.0022(17) 0.0093(16) 0.0005(19) C3 0.041(2) 0.060(3) 0.037(2) -0.007(2) 0.0156(17) -0.006(2) C4 0.038(2) 0.069(4) 0.041(2) -0.006(2) 0.0045(18) 0.005(2) C5 0.042(2) 0.051(3) 0.032(2) -0.0017(19) 0.0053(17) -0.002(2) C6 0.043(2) 0.043(3) 0.0307(19) -0.0045(18) 0.0132(16) -0.005(2) C7 0.034(2) 0.042(3) 0.0285(18) -0.0056(18) 0.0086(15) -0.0015(19) C8 0.034(2) 0.038(3) 0.0329(19) -0.0025(17) 0.0094(16) -0.0006(18) C9 0.042(2) 0.042(3) 0.0266(19) -0.0022(17) 0.0041(16) 0.0050(19) C10 0.036(2) 0.056(3) 0.039(2) -0.008(2) 0.0034(17) -0.010(2) C11 0.043(2) 0.048(3) 0.036(2) -0.003(2) 0.0122(18) -0.016(2) C12 0.040(2) 0.047(3) 0.0250(18) -0.0019(18) 0.0071(16) 0.000(2) C13 0.065(3) 0.035(3) 0.043(2) -0.009(2) 0.016(2) -0.003(2) C14 0.050(2) 0.042(3) 0.034(2) -0.003(2) 0.0023(17) -0.012(2) C15 0.091(4) 0.051(4) 0.043(3) -0.003(2) 0.007(2) -0.009(3) C16 0.053(3) 0.043(3) 0.050(3) -0.004(2) 0.011(2) 0.007(2) C17 0.051(3) 0.042(3) 0.037(2) -0.005(2) 0.0155(18) -0.007(2) C18 0.090(4) 0.070(4) 0.033(2) 0.008(2) 0.005(2) 0.001(3) C19 0.041(2) 0.037(3) 0.040(2) -0.0053(19) 0.0106(18) -0.004(2) C20 0.062(3) 0.053(3) 0.035(2) -0.001(2) 0.0102(19) -0.001(2) C21 0.046(2) 0.068(4) 0.041(2) -0.008(2) 0.0105(19) 0.002(2) C22 0.041(3) 0.104(5) 0.063(3) -0.026(3) -0.004(2) 0.013(3) O7 0.115(6) 0.085(6) 0.093(5) 0.015(5) 0.007(4) -0.002(5) C23 0.074(5) 0.077(7) 0.047(4) -0.015(5) 0.018(4) -0.012(5) O7' 0.060(5) 0.178(9) 0.112(7) -0.089(7) 0.021(5) -0.040(6) C23' 0.080(9) 0.089(10) 0.060(8) -0.015(8) 0.006(7) 0.002(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.340(5) . ? N1 C9 1.464(5) . ? N1 C13 1.469(5) . ? O1 C1 1.218(5) . ? O2 C17 1.197(5) . ? O3 C17 1.329(5) . ? O3 C18 1.450(5) . ? O4 C19 1.358(5) . ? O4 C12 1.418(4) . ? O5 C19 1.188(5) . ? O6 C22 1.272(5) . ? O6 C21 1.446(5) . ? C1 C2 1.549(6) . ? C2 C17 1.518(6) . ? C2 C3 1.540(5) . ? C2 C8 1.596(5) . ? C3 C4 1.537(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.532(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C21 1.496(6) . ? C5 C6 1.533(5) . ? C5 H5 0.9800 . ? C6 C7 1.512(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.333(6) . ? C7 C8 1.529(5) . ? C8 C16 1.526(6) . ? C8 C9 1.541(5) . ? C9 C10 1.518(6) . ? C9 H9 0.9800 . ? C10 C11 1.515(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.503(6) . ? C11 C14 1.529(6) . ? C11 H11 0.9800 . ? C13 C14 1.516(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.311(7) . ? C15 H15A 0.9300 . ? C15 H15B 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.485(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 O7' 1.188(9) . ? C22 O7 1.278(9) . ? C22 C23' 1.44(2) . ? C22 C23 1.456(11) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C23' H23D 0.9600 . ? C23' H23E 0.9600 . ? C23' H23F 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 C1 N1 C9 113.5(4) . . ? C1 N1 C13 123.2(4) . . ? C9 N1 C13 119.6(3) . . ? C17 O3 C18 116.5(4) . . ? C19 O4 C12 116.0(3) . . ? C22 O6 C21 122.0(4) . . ? O1 C1 N1 126.7(4) . . ? O1 C1 C2 124.8(4) . . ? N1 C1 C2 108.4(3) . . ? C17 C2 C3 106.9(3) . . ? C17 C2 C1 110.6(3) . . ? C3 C2 C1 109.9(3) . . ? C17 C2 C8 108.9(3) . . ? C3 C2 C8 118.9(3) . . ? C1 C2 C8 101.5(3) . . ? C4 C3 C2 115.9(4) . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C5 C4 C3 114.9(4) . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C21 C5 C4 109.1(3) . . ? C21 C5 C6 112.7(4) . . ? C4 C5 C6 111.3(3) . . ? C21 C5 H5 107.9 . . ? C4 C5 H5 107.9 . . ? C6 C5 H5 107.9 . . ? C7 C6 C5 112.6(3) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C12 C7 C6 121.3(3) . . ? C12 C7 C8 120.7(3) . . ? C6 C7 C8 118.0(4) . . ? C16 C8 C7 110.2(3) . . ? C16 C8 C9 111.2(3) . . ? C7 C8 C9 110.2(3) . . ? C16 C8 C2 114.0(3) . . ? C7 C8 C2 110.2(3) . . ? C9 C8 C2 100.8(3) . . ? N1 C9 C10 110.2(4) . . ? N1 C9 C8 102.9(3) . . ? C10 C9 C8 114.1(3) . . ? N1 C9 H9 109.8 . . ? C10 C9 H9 109.8 . . ? C8 C9 H9 109.8 . . ? C11 C10 C9 107.1(3) . . ? C11 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? C11 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? H10A C10 H10B 108.6 . . ? C12 C11 C10 107.4(4) . . ? C12 C11 C14 112.1(3) . . ? C10 C11 C14 110.0(3) . . ? C12 C11 H11 109.1 . . ? C10 C11 H11 109.1 . . ? C14 C11 H11 109.1 . . ? C7 C12 O4 119.4(3) . . ? C7 C12 C11 127.2(3) . . ? O4 C12 C11 113.4(3) . . ? N1 C13 C14 108.6(3) . . ? N1 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? N1 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C13 122.4(4) . . ? C15 C14 C11 123.3(4) . . ? C13 C14 C11 114.3(4) . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 O3 123.1(4) . . ? O2 C17 C2 124.3(4) . . ? O3 C17 C2 112.6(4) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 O4 122.4(4) . . ? O5 C19 C20 126.1(4) . . ? O4 C19 C20 111.5(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O6 C21 C5 111.0(3) . . ? O6 C21 H21A 109.4 . . ? C5 C21 H21A 109.4 . . ? O6 C21 H21B 109.4 . . ? C5 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? O7' C22 O6 118.3(6) . . ? O7' C22 O7 57.0(6) . . ? O6 C22 O7 112.3(6) . . ? O7' C22 C23' 123.4(10) . . ? O6 C22 C23' 118.1(10) . . ? O7 C22 C23' 97.1(11) . . ? O7' C22 C23 113.9(7) . . ? O6 C22 C23 119.8(6) . . ? O7 C22 C23 120.2(7) . . ? C23' C22 C23 33.0(9) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? C22 C23' H23D 109.5 . . ? C22 C23' H23E 109.5 . . ? H23D C23' H23E 109.5 . . ? C22 C23' H23F 109.5 . . ? H23D C23' H23F 109.5 . . ? H23E C23' H23F 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 C9 N1 C1 O1 178.8(4) . . . . ? C13 N1 C1 O1 -22.9(6) . . . . ? C9 N1 C1 C2 -4.2(4) . . . . ? C13 N1 C1 C2 154.0(3) . . . . ? O1 C1 C2 C17 -85.7(5) . . . . ? N1 C1 C2 C17 97.2(4) . . . . ? O1 C1 C2 C3 32.0(5) . . . . ? N1 C1 C2 C3 -145.0(3) . . . . ? O1 C1 C2 C8 158.8(4) . . . . ? N1 C1 C2 C8 -18.3(4) . . . . ? C17 C2 C3 C4 174.9(3) . . . . ? C1 C2 C3 C4 54.9(4) . . . . ? C8 C2 C3 C4 -61.4(5) . . . . ? C2 C3 C4 C5 90.3(5) . . . . ? C3 C4 C5 C21 84.4(5) . . . . ? C3 C4 C5 C6 -40.6(5) . . . . ? C21 C5 C6 C7 -164.8(3) . . . . ? C4 C5 C6 C7 -41.9(5) . . . . ? C5 C6 C7 C12 -80.1(5) . . . . ? C5 C6 C7 C8 99.5(4) . . . . ? C12 C7 C8 C16 -120.4(4) . . . . ? C6 C7 C8 C16 60.0(4) . . . . ? C12 C7 C8 C9 2.6(5) . . . . ? C6 C7 C8 C9 -177.0(3) . . . . ? C12 C7 C8 C2 113.0(4) . . . . ? C6 C7 C8 C2 -66.7(4) . . . . ? C17 C2 C8 C16 34.2(4) . . . . ? C3 C2 C8 C16 -88.5(4) . . . . ? C1 C2 C8 C16 151.0(3) . . . . ? C17 C2 C8 C7 158.7(3) . . . . ? C3 C2 C8 C7 36.1(5) . . . . ? C1 C2 C8 C7 -84.5(4) . . . . ? C17 C2 C8 C9 -84.9(4) . . . . ? C3 C2 C8 C9 152.4(4) . . . . ? C1 C2 C8 C9 31.8(3) . . . . ? C1 N1 C9 C10 147.9(3) . . . . ? C13 N1 C9 C10 -11.3(4) . . . . ? C1 N1 C9 C8 25.8(4) . . . . ? C13 N1 C9 C8 -133.3(3) . . . . ? C16 C8 C9 N1 -155.6(3) . . . . ? C7 C8 C9 N1 81.9(3) . . . . ? C2 C8 C9 N1 -34.4(4) . . . . ? C16 C8 C9 C10 85.0(4) . . . . ? C7 C8 C9 C10 -37.5(4) . . . . ? C2 C8 C9 C10 -153.8(3) . . . . ? N1 C9 C10 C11 -49.0(4) . . . . ? C8 C9 C10 C11 66.2(4) . . . . ? C9 C10 C11 C12 -55.4(4) . . . . ? C9 C10 C11 C14 66.8(4) . . . . ? C6 C7 C12 O4 1.6(6) . . . . ? C8 C7 C12 O4 -178.0(3) . . . . ? C6 C7 C12 C11 -177.2(4) . . . . ? C8 C7 C12 C11 3.2(6) . . . . ? C19 O4 C12 C7 -102.3(4) . . . . ? C19 O4 C12 C11 76.7(4) . . . . ? C10 C11 C12 C7 24.5(6) . . . . ? C14 C11 C12 C7 -96.3(5) . . . . ? C10 C11 C12 O4 -154.3(3) . . . . ? C14 C11 C12 O4 84.8(4) . . . . ? C1 N1 C13 C14 -103.0(4) . . . . ? C9 N1 C13 C14 54.0(5) . . . . ? N1 C13 C14 C15 147.7(4) . . . . ? N1 C13 C14 C11 -33.3(5) . . . . ? C12 C11 C14 C15 -85.1(5) . . . . ? C10 C11 C14 C15 155.5(4) . . . . ? C12 C11 C14 C13 95.9(4) . . . . ? C10 C11 C14 C13 -23.5(5) . . . . ? C18 O3 C17 O2 -1.0(6) . . . . ? C18 O3 C17 C2 178.8(4) . . . . ? C3 C2 C17 O2 38.8(6) . . . . ? C1 C2 C17 O2 158.4(4) . . . . ? C8 C2 C17 O2 -90.8(5) . . . . ? C3 C2 C17 O3 -140.9(4) . . . . ? C1 C2 C17 O3 -21.3(5) . . . . ? C8 C2 C17 O3 89.4(4) . . . . ? C12 O4 C19 O5 4.4(6) . . . . ? C12 O4 C19 C20 -176.1(4) . . . . ? C22 O6 C21 C5 -145.1(5) . . . . ? C4 C5 C21 O6 -179.5(4) . . . . ? C6 C5 C21 O6 -55.3(5) . . . . ? C21 O6 C22 O7' -15.9(11) . . . . ? C21 O6 C22 O7 47.4(9) . . . . ? C21 O6 C22 C23' 159.1(12) . . . . ? C21 O6 C22 C23 -163.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.057 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 963869'