# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_6 _database_code_depnum_ccdc_archive 'CCDC 905361' #TrackingRef 'EJOC 10-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N1 O1' _chemical_formula_weight 175.22 _chemical_compound_source 'Alan Spivey' 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/n ' _symmetry_Int_Tables_number 14 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 7.192(3) _cell_length_b 14.069(4) _cell_length_c 9.2117(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.365(19) _cell_angle_gamma 90.00 _cell_volume 910.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.25 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku RU200 Rotating Mo Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.54 _diffrn_reflns_number 2137 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.97 _reflns_number_total 1984 _reflns_number_gt 1664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution 'SHELXTL (Bruker AXS)' _computing_structure_refinement 'SHELXTL (Bruker AXS)' _computing_molecular_graphics 'SHELXTL (Bruker AXS)' _computing_publication_material 'SHELXTL (Bruker AXS)' _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^)+(0.0650P)^2^+0.4000P] 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_number_reflns 1984 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.02055(12) 0.12038(7) 0.68158(11) 0.0232(3) Uani 1 1 d . . . H1A H -0.040(3) 0.1170(13) 0.751(2) 0.043(5) Uiso 1 1 d . . . N1 N 0.69654(15) 0.11746(8) 0.82030(12) 0.0210(3) Uani 1 1 d . . . C1 C 0.34029(17) 0.17335(9) 0.74721(13) 0.0172(3) Uani 1 1 d . . . C2 C 0.31140(18) 0.22499(9) 0.59633(14) 0.0196(3) Uani 1 1 d . . . H2A H 0.1894 0.2602 0.5788 0.024 Uiso 1 1 calc R . . H2B H 0.4149 0.2719 0.6002 0.024 Uiso 1 1 calc R . . C3 C 0.30957(18) 0.15824(10) 0.46894(14) 0.0226(3) Uani 1 1 d . . . H3A H 0.3290 0.1838 0.3779 0.027 Uiso 1 1 calc R . . C4 C 0.28215(18) 0.06544(10) 0.47719(14) 0.0223(3) Uani 1 1 d . . . H4A H 0.2808 0.0281 0.3911 0.027 Uiso 1 1 calc R . . C5 C 0.25315(17) 0.01608(9) 0.61509(14) 0.0198(3) Uani 1 1 d . . . H5A H 0.3693 -0.0205 0.6583 0.024 Uiso 1 1 calc R . . H5B H 0.1468 -0.0296 0.5875 0.024 Uiso 1 1 calc R . . C6 C 0.20928(16) 0.08421(9) 0.73354(14) 0.0182(3) Uani 1 1 d . . . C7 C 0.23179(18) 0.03300(9) 0.88327(14) 0.0207(3) Uani 1 1 d . . . H7A H 0.1218 -0.0100 0.8791 0.025 Uiso 1 1 calc R . . H7B H 0.3481 -0.0067 0.8993 0.025 Uiso 1 1 calc R . . C8 C 0.24508(18) 0.09921(10) 1.01334(14) 0.0236(3) Uani 1 1 d . . . H8A H 0.2303 0.0733 1.1054 0.028 Uiso 1 1 calc R . . C9 C 0.27621(18) 0.19179(10) 1.00641(14) 0.0232(3) Uani 1 1 d . . . H9A H 0.2852 0.2284 1.0942 0.028 Uiso 1 1 calc R . . C10 C 0.29799(18) 0.24163(9) 0.86726(14) 0.0198(3) Uani 1 1 d . . . H10A H 0.4028 0.2884 0.8924 0.024 Uiso 1 1 calc R . . H10B H 0.1795 0.2771 0.8261 0.024 Uiso 1 1 calc R . . C11 C 0.54069(17) 0.14103(9) 0.78958(13) 0.0183(3) 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 0.0112(4) 0.0368(6) 0.0217(5) 0.0021(4) 0.0036(4) 0.0019(4) N1 0.0155(5) 0.0270(6) 0.0208(5) -0.0015(4) 0.0045(4) 0.0006(4) C1 0.0156(6) 0.0188(6) 0.0175(6) 0.0001(4) 0.0041(4) 0.0006(4) C2 0.0188(6) 0.0202(6) 0.0200(6) 0.0045(5) 0.0049(5) 0.0006(5) C3 0.0197(6) 0.0322(7) 0.0169(6) 0.0029(5) 0.0060(5) 0.0027(5) C4 0.0180(6) 0.0316(7) 0.0175(6) -0.0057(5) 0.0042(5) 0.0015(5) C5 0.0182(6) 0.0194(6) 0.0216(6) -0.0031(5) 0.0038(5) -0.0011(5) C6 0.0145(6) 0.0203(6) 0.0197(6) 0.0003(5) 0.0039(4) -0.0003(4) C7 0.0192(6) 0.0223(6) 0.0212(6) 0.0035(5) 0.0057(5) -0.0026(5) C8 0.0192(6) 0.0355(8) 0.0176(6) 0.0030(5) 0.0071(5) -0.0001(5) C9 0.0194(6) 0.0335(8) 0.0177(6) -0.0049(5) 0.0064(5) 0.0019(5) C10 0.0182(6) 0.0198(6) 0.0217(6) -0.0038(5) 0.0049(5) 0.0013(5) C11 0.0178(6) 0.0219(6) 0.0162(6) -0.0020(5) 0.0061(5) -0.0020(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 O1 C6 1.4325(15) . yes O1 H1A 0.85(2) . yes N1 C11 1.1447(17) . yes C1 C11 1.4817(17) . yes C1 C2 1.5424(16) . yes C1 C10 1.5435(16) . yes C1 C6 1.5574(18) . yes C2 C3 1.5009(18) . yes C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.325(2) . yes C3 H3A 0.9500 . ? C4 C5 1.5009(18) . yes C4 H4A 0.9500 . ? C5 C6 1.5351(17) . yes C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5337(17) . yes C7 C8 1.5045(18) . yes C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.325(2) . yes C8 H8A 0.9500 . ? C9 C10 1.4985(17) . yes C9 H9A 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 C6 O1 H1A 109.5(14) . . yes C11 C1 C2 108.52(10) . . yes C11 C1 C10 109.40(10) . . yes C2 C1 C10 110.07(10) . . yes C11 C1 C6 108.15(10) . . yes C2 C1 C6 110.13(10) . . yes C10 C1 C6 110.52(10) . . yes C3 C2 C1 112.75(11) . . yes C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 123.25(12) . . yes C4 C3 H3A 118.4 . . ? C2 C3 H3A 118.4 . . ? C3 C4 C5 123.63(12) . . yes C3 C4 H4A 118.2 . . ? C5 C4 H4A 118.2 . . ? C4 C5 C6 113.55(11) . . yes C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 C6 C7 112.17(10) . . yes O1 C6 C5 107.97(10) . . yes C7 C6 C5 110.35(10) . . yes O1 C6 C1 104.74(10) . . yes C7 C6 C1 111.11(10) . . yes C5 C6 C1 110.33(10) . . yes C8 C7 C6 113.69(11) . . yes C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 123.55(12) . . yes C9 C8 H8A 118.2 . . ? C7 C8 H8A 118.2 . . ? C8 C9 C10 123.42(12) . . yes C8 C9 H9A 118.3 . . ? C10 C9 H9A 118.3 . . ? C9 C10 C1 113.22(11) . . yes C9 C10 H10A 108.9 . . ? C1 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C1 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? N1 C11 C1 178.54(14) . . yes 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 C11 C1 C2 C3 72.44(13) . . . . yes C10 C1 C2 C3 -167.87(10) . . . . yes C6 C1 C2 C3 -45.77(13) . . . . yes C1 C2 C3 C4 17.68(17) . . . . yes C2 C3 C4 C5 -1.1(2) . . . . yes C3 C4 C5 C6 14.17(18) . . . . yes C4 C5 C6 O1 71.47(13) . . . . yes C4 C5 C6 C7 -165.61(10) . . . . yes C4 C5 C6 C1 -42.44(14) . . . . yes C11 C1 C6 O1 -175.70(9) . . . . yes C2 C1 C6 O1 -57.26(12) . . . . yes C10 C1 C6 O1 64.58(12) . . . . yes C11 C1 C6 C7 62.98(13) . . . . yes C2 C1 C6 C7 -178.58(9) . . . . yes C10 C1 C6 C7 -56.75(13) . . . . yes C11 C1 C6 C5 -59.74(12) . . . . yes C2 C1 C6 C5 58.70(13) . . . . yes C10 C1 C6 C5 -179.47(10) . . . . yes O1 C6 C7 C8 -75.56(13) . . . . yes C5 C6 C7 C8 164.01(10) . . . . yes C1 C6 C7 C8 41.30(14) . . . . yes C6 C7 C8 C9 -13.95(18) . . . . yes C7 C8 C9 C10 1.3(2) . . . . yes C8 C9 C10 C1 -17.11(17) . . . . yes C11 C1 C10 C9 -74.89(13) . . . . yes C2 C1 C10 C9 165.95(10) . . . . yes C6 C1 C10 C9 44.09(14) . . . . yes C2 C1 C11 N1 21(6) . . . . yes C10 C1 C11 N1 -99(6) . . . . yes C6 C1 C11 N1 140(6) . . . . yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.85(2) 2.12(2) 2.8879(16) 149.7(19) 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.355 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.056 data_17 _database_code_depnum_ccdc_archive 'CCDC 905362' #TrackingRef 'EJOC 10-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 03csf003 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N1 O4' _chemical_formula_weight 381.46 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 6.2151(2) _cell_length_b 16.8252(5) _cell_length_c 9.7311(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.1760(10) _cell_angle_gamma 90.00 _cell_volume 1017.58(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 2311 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 Rotating anode' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'graded mirror' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12036 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4019 _reflns_number_gt 3150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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. ; _chemical_absolute_configuration unk _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^)+(0.0600P)^2^+0.1200P] 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 -0.9(12) _refine_ls_number_reflns 4019 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.6507(3) 0.25093(11) 0.52867(18) 0.0247(4) Uani 1 1 d . . . O2 O 1.2554(3) 0.41643(11) 0.60530(17) 0.0244(4) Uani 1 1 d . . . O3 O 1.0034(3) 0.54883(12) 0.8452(2) 0.0318(5) Uani 1 1 d . . . H3B H 1.012(5) 0.530(2) 0.926(4) 0.041(10) Uiso 1 1 d . . . O4 O 0.8823(3) 0.16034(13) 0.6123(2) 0.0384(5) Uani 1 1 d . . . N1 N 1.0219(4) 0.47246(17) 0.1168(2) 0.0406(7) Uani 1 1 d . . . C1 C 0.6116(4) 0.38409(17) 0.3166(3) 0.0273(6) Uani 1 1 d . . . H1A H 0.5147 0.3879 0.3968 0.033 Uiso 1 1 calc R . . H1B H 0.5317 0.4041 0.2355 0.033 Uiso 1 1 calc R . . C2 C 0.6661(5) 0.29662(17) 0.2928(3) 0.0285(6) Uani 1 1 d . . . H2A H 0.5275 0.2665 0.2901 0.034 Uiso 1 1 calc R . . C3 C 0.7988(4) 0.26424(17) 0.4128(3) 0.0263(6) Uani 1 1 d . . . H3A H 0.8686 0.2130 0.3860 0.032 Uiso 1 1 calc R . . C4 C 0.9656(4) 0.32155(17) 0.4647(3) 0.0249(6) Uani 1 1 d . . . H4A H 1.0798 0.3006 0.5187 0.030 Uiso 1 1 calc R . . C5 C 0.9657(4) 0.39854(16) 0.4410(2) 0.0211(6) Uani 1 1 d . . . C6 C 1.1079(4) 0.45700(15) 0.5155(3) 0.0208(5) Uani 1 1 d . . . H6A H 1.1911 0.4887 0.4468 0.025 Uiso 1 1 calc R . . C7 C 0.9723(4) 0.51409(16) 0.6054(2) 0.0193(5) Uani 1 1 d . . . H7A H 1.0393 0.5680 0.5992 0.023 Uiso 1 1 calc R . . C8 C 0.7384(4) 0.52154(16) 0.5556(3) 0.0215(6) Uani 1 1 d . . . H8A H 0.6551 0.4747 0.5899 0.026 Uiso 1 1 calc R . . C9 C 0.7344(4) 0.52086(16) 0.3985(3) 0.0248(6) Uani 1 1 d . . . H9A H 0.8315 0.5628 0.3633 0.030 Uiso 1 1 calc R . . H9B H 0.5869 0.5327 0.3657 0.030 Uiso 1 1 calc R . . C10 C 0.8072(4) 0.43842(16) 0.3416(3) 0.0236(6) Uani 1 1 d . . . C11 C 1.0109(4) 0.48297(16) 0.7523(3) 0.0227(6) Uani 1 1 d . . . C12 C 1.2402(4) 0.45200(17) 0.7391(3) 0.0264(6) Uani 1 1 d . . . H12A H 1.3446 0.4961 0.7483 0.032 Uiso 1 1 calc R . . H12B H 1.2707 0.4122 0.8114 0.032 Uiso 1 1 calc R . . C13 C 0.7848(6) 0.2802(2) 0.1573(3) 0.0423(8) Uani 1 1 d . . . H13A H 0.7956 0.2227 0.1430 0.063 Uiso 1 1 calc R . . H13B H 0.9295 0.3032 0.1618 0.063 Uiso 1 1 calc R . . H13C H 0.7049 0.3042 0.0809 0.063 Uiso 1 1 calc R . . C14 C 0.6348(5) 0.59765(17) 0.6115(3) 0.0299(6) Uani 1 1 d . . . H14A H 0.4836 0.5998 0.5830 0.045 Uiso 1 1 calc R . . H14B H 0.7112 0.6441 0.5753 0.045 Uiso 1 1 calc R . . H14C H 0.6436 0.5977 0.7121 0.045 Uiso 1 1 calc R . . C15 C 0.8573(4) 0.41733(17) 0.7981(3) 0.0265(6) Uani 1 1 d . . . H15A H 0.8582 0.3742 0.7304 0.040 Uiso 1 1 calc R . . H15B H 0.7114 0.4389 0.8058 0.040 Uiso 1 1 calc R . . H15C H 0.9036 0.3967 0.8876 0.040 Uiso 1 1 calc R . . C16 C 0.9254(4) 0.45539(17) 0.2125(3) 0.0282(6) Uani 1 1 d . . . C17 C 0.7178(4) 0.19864(15) 0.6241(3) 0.0248(6) Uani 1 1 d . . . C18 C 0.5701(4) 0.19173(15) 0.7428(3) 0.0247(6) Uani 1 1 d . . . C19 C 0.3855(4) 0.23774(17) 0.7538(3) 0.0314(7) Uani 1 1 d . . . H19A H 0.3530 0.2765 0.6858 0.038 Uiso 1 1 calc R . . C20 C 0.2487(5) 0.2267(2) 0.8648(3) 0.0412(8) Uani 1 1 d . . . H20A H 0.1218 0.2579 0.8723 0.049 Uiso 1 1 calc R . . C21 C 0.2958(5) 0.17071(19) 0.9645(3) 0.0388(8) Uani 1 1 d . . . H21A H 0.2010 0.1634 1.0399 0.047 Uiso 1 1 calc R . . C22 C 0.4804(5) 0.12548(19) 0.9546(3) 0.0380(8) Uani 1 1 d . . . H22A H 0.5133 0.0874 1.0236 0.046 Uiso 1 1 calc R . . C23 C 0.6174(5) 0.13571(17) 0.8443(3) 0.0324(7) Uani 1 1 d . . . H23A H 0.7443 0.1045 0.8376 0.039 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 0.0287(9) 0.0213(10) 0.0241(10) 0.0032(8) 0.0002(7) -0.0013(8) O2 0.0219(9) 0.0292(11) 0.0221(9) -0.0019(8) -0.0029(7) 0.0034(8) O3 0.0471(12) 0.0297(11) 0.0186(11) -0.0022(9) -0.0005(9) 0.0023(9) O4 0.0465(13) 0.0359(12) 0.0328(12) 0.0008(9) 0.0032(9) 0.0175(10) N1 0.0546(17) 0.0437(16) 0.0234(14) 0.0004(12) -0.0015(12) -0.0191(13) C1 0.0299(15) 0.0313(16) 0.0208(14) 0.0023(12) -0.0045(11) -0.0068(12) C2 0.0338(15) 0.0292(16) 0.0225(15) -0.0039(12) -0.0005(11) -0.0099(12) C3 0.0319(15) 0.0240(15) 0.0229(15) -0.0011(12) 0.0053(11) -0.0015(12) C4 0.0232(14) 0.0274(16) 0.0240(14) -0.0030(12) 0.0028(11) 0.0033(11) C5 0.0227(13) 0.0249(15) 0.0159(13) -0.0002(11) 0.0034(10) 0.0010(11) C6 0.0221(12) 0.0222(14) 0.0181(13) 0.0009(11) 0.0016(10) 0.0000(11) C7 0.0222(13) 0.0184(13) 0.0173(13) 0.0001(10) 0.0021(10) -0.0024(11) C8 0.0222(13) 0.0199(13) 0.0225(14) 0.0030(11) 0.0004(10) 0.0036(11) C9 0.0279(14) 0.0224(14) 0.0241(15) 0.0039(12) -0.0036(11) -0.0014(11) C10 0.0303(14) 0.0260(15) 0.0144(12) 0.0018(11) -0.0003(10) -0.0043(11) C11 0.0288(14) 0.0236(14) 0.0158(13) -0.0023(11) -0.0012(10) 0.0006(11) C12 0.0248(14) 0.0306(16) 0.0238(14) 0.0023(12) -0.0045(10) -0.0028(11) C13 0.060(2) 0.0358(19) 0.0310(17) -0.0084(14) 0.0011(14) -0.0120(16) C14 0.0325(15) 0.0240(15) 0.0331(16) 0.0021(13) 0.0024(12) 0.0062(12) C15 0.0264(14) 0.0299(15) 0.0231(14) 0.0048(12) -0.0016(10) 0.0009(12) C16 0.0369(15) 0.0271(16) 0.0206(15) -0.0005(12) -0.0067(12) -0.0080(12) C17 0.0352(16) 0.0161(14) 0.0230(15) -0.0048(11) -0.0043(11) 0.0018(12) C18 0.0309(15) 0.0179(14) 0.0252(15) -0.0004(11) -0.0052(11) -0.0016(11) C19 0.0328(15) 0.0279(17) 0.0335(16) 0.0107(13) -0.0012(12) 0.0022(13) C20 0.0357(16) 0.0431(19) 0.0450(19) 0.0129(16) 0.0056(14) 0.0083(15) C21 0.0445(18) 0.0380(19) 0.0341(18) 0.0079(15) 0.0059(14) -0.0049(15) C22 0.0497(19) 0.0357(19) 0.0286(17) 0.0127(14) -0.0042(14) -0.0016(15) C23 0.0419(17) 0.0262(16) 0.0290(16) 0.0028(13) -0.0074(12) 0.0030(13) _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 C17 1.345(3) . yes O1 C3 1.474(3) . yes O2 C12 1.437(3) . yes O2 C6 1.437(3) . yes O3 C11 1.431(3) . yes O3 H3B 0.85(4) . yes O4 C17 1.214(3) . yes N1 C16 1.146(4) . yes C1 C2 1.528(4) . yes C1 C10 1.540(4) . yes C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.528(4) . yes C2 C13 1.537(4) . yes C2 H2A 1.0000 . ? C3 C4 1.502(4) . yes C3 H3A 1.0000 . ? C4 C5 1.316(4) . yes C4 H4A 0.9500 . ? C5 C6 1.507(4) . yes C5 C10 1.533(4) . yes C6 C7 1.550(4) . yes C6 H6A 1.0000 . ? C7 C8 1.536(3) . yes C7 C11 1.540(3) . yes C7 H7A 1.0000 . ? C8 C9 1.529(4) . yes C8 C14 1.534(4) . yes C8 H8A 1.0000 . ? C9 C10 1.561(4) . yes C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C16 1.485(4) . yes C11 C12 1.523(4) . yes C11 C15 1.527(4) . yes C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.482(4) . yes C18 C19 1.388(4) . yes C18 C23 1.396(4) . yes C19 C20 1.389(4) . yes C19 H19A 0.9500 . ? C20 C21 1.384(4) . yes C20 H20A 0.9500 . ? C21 C22 1.380(5) . yes C21 H21A 0.9500 . ? C22 C23 1.383(4) . yes C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? 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 C17 O1 C3 115.8(2) . . yes C12 O2 C6 108.06(18) . . yes C11 O3 H3B 107(2) . . yes C2 C1 C10 114.9(2) . . yes C2 C1 H1A 108.5 . . ? C10 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? C10 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C1 C2 C3 110.3(2) . . yes C1 C2 C13 114.2(2) . . yes C3 C2 C13 109.4(2) . . yes C1 C2 H2A 107.6 . . ? C3 C2 H2A 107.6 . . ? C13 C2 H2A 107.6 . . ? O1 C3 C4 105.8(2) . . yes O1 C3 C2 107.6(2) . . yes C4 C3 C2 113.5(2) . . yes O1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C5 C4 C3 125.0(2) . . yes C5 C4 H4A 117.5 . . ? C3 C4 H4A 117.5 . . ? C4 C5 C6 124.0(2) . . yes C4 C5 C10 122.7(2) . . yes C6 C5 C10 113.1(2) . . yes O2 C6 C5 110.8(2) . . yes O2 C6 C7 107.31(19) . . yes C5 C6 C7 110.9(2) . . yes O2 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C8 C7 C11 117.7(2) . . yes C8 C7 C6 112.8(2) . . yes C11 C7 C6 103.3(2) . . yes C8 C7 H7A 107.5 . . ? C11 C7 H7A 107.5 . . ? C6 C7 H7A 107.5 . . ? C9 C8 C14 110.8(2) . . yes C9 C8 C7 109.1(2) . . yes C14 C8 C7 110.7(2) . . yes C9 C8 H8A 108.7 . . ? C14 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C8 C9 C10 110.9(2) . . yes C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? C16 C10 C5 107.4(2) . . yes C16 C10 C1 111.9(2) . . yes C5 C10 C1 110.2(2) . . yes C16 C10 C9 105.9(2) . . yes C5 C10 C9 110.6(2) . . yes C1 C10 C9 110.8(2) . . yes O3 C11 C12 110.5(2) . . yes O3 C11 C15 110.7(2) . . yes C12 C11 C15 111.3(2) . . yes O3 C11 C7 108.5(2) . . yes C12 C11 C7 100.4(2) . . yes C15 C11 C7 114.9(2) . . yes O2 C12 C11 106.44(19) . . yes O2 C12 H12A 110.4 . . ? C11 C12 H12A 110.4 . . ? O2 C12 H12B 110.4 . . ? C11 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C10 175.8(3) . . yes O4 C17 O1 122.8(3) . . yes O4 C17 C18 123.8(2) . . yes O1 C17 C18 113.5(2) . . yes C19 C18 C23 119.6(3) . . yes C19 C18 C17 122.0(2) . . yes C23 C18 C17 118.3(2) . . yes C18 C19 C20 119.6(3) . . yes C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C21 C20 C19 120.5(3) . . yes C21 C20 H20A 119.7 . . ? C19 C20 H20A 119.7 . . ? C22 C21 C20 120.1(3) . . yes C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.0(3) . . yes C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C22 C23 C18 120.3(3) . . yes C22 C23 H23A 119.9 . . ? C18 C23 H23A 119.9 . . ? 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 C10 C1 C2 C3 55.7(3) . . . . yes C10 C1 C2 C13 -68.0(3) . . . . yes C17 O1 C3 C4 -80.5(3) . . . . yes C17 O1 C3 C2 157.9(2) . . . . yes C1 C2 C3 O1 76.2(3) . . . . yes C13 C2 C3 O1 -157.4(2) . . . . yes C1 C2 C3 C4 -40.5(3) . . . . yes C13 C2 C3 C4 85.9(3) . . . . yes O1 C3 C4 C5 -99.3(3) . . . . yes C2 C3 C4 C5 18.4(4) . . . . yes C3 C4 C5 C6 167.6(2) . . . . yes C3 C4 C5 C10 -7.6(4) . . . . yes C12 O2 C6 C5 -128.9(2) . . . . yes C12 O2 C6 C7 -7.7(2) . . . . yes C4 C5 C6 O2 5.4(3) . . . . yes C10 C5 C6 O2 -179.04(18) . . . . yes C4 C5 C6 C7 -113.7(3) . . . . yes C10 C5 C6 C7 61.9(3) . . . . yes O2 C6 C7 C8 -144.5(2) . . . . yes C5 C6 C7 C8 -23.4(3) . . . . yes O2 C6 C7 C11 -16.3(2) . . . . yes C5 C6 C7 C11 104.8(2) . . . . yes C11 C7 C8 C9 -157.9(2) . . . . yes C6 C7 C8 C9 -37.7(3) . . . . yes C11 C7 C8 C14 79.9(3) . . . . yes C6 C7 C8 C14 -159.9(2) . . . . yes C14 C8 C9 C10 -171.4(2) . . . . yes C7 C8 C9 C10 66.5(3) . . . . yes C4 C5 C10 C16 -102.7(3) . . . . yes C6 C5 C10 C16 81.7(3) . . . . yes C4 C5 C10 C1 19.4(3) . . . . yes C6 C5 C10 C1 -156.2(2) . . . . yes C4 C5 C10 C9 142.2(2) . . . . yes C6 C5 C10 C9 -33.4(3) . . . . yes C2 C1 C10 C16 75.6(3) . . . . yes C2 C1 C10 C5 -43.9(3) . . . . yes C2 C1 C10 C9 -166.6(2) . . . . yes C8 C9 C10 C16 -145.5(2) . . . . yes C8 C9 C10 C5 -29.4(3) . . . . yes C8 C9 C10 C1 93.0(2) . . . . yes C8 C7 C11 O3 -87.0(3) . . . . yes C6 C7 C11 O3 148.0(2) . . . . yes C8 C7 C11 C12 157.1(2) . . . . yes C6 C7 C11 C12 32.0(2) . . . . yes C8 C7 C11 C15 37.6(3) . . . . yes C6 C7 C11 C15 -87.5(3) . . . . yes C6 O2 C12 C11 29.5(3) . . . . yes O3 C11 C12 O2 -152.7(2) . . . . yes C15 C11 C12 O2 83.8(3) . . . . yes C7 C11 C12 O2 -38.3(3) . . . . yes C5 C10 C16 N1 -79(4) . . . . yes C1 C10 C16 N1 160(4) . . . . yes C9 C10 C16 N1 39(4) . . . . yes C3 O1 C17 O4 -4.9(4) . . . . yes C3 O1 C17 C18 176.0(2) . . . . yes O4 C17 C18 C19 178.7(3) . . . . yes O1 C17 C18 C19 -2.2(4) . . . . yes O4 C17 C18 C23 -2.8(4) . . . . yes O1 C17 C18 C23 176.3(2) . . . . yes C23 C18 C19 C20 -0.8(4) . . . . yes C17 C18 C19 C20 177.7(3) . . . . yes C18 C19 C20 C21 0.4(5) . . . . yes C19 C20 C21 C22 0.3(5) . . . . yes C20 C21 C22 C23 -0.6(5) . . . . yes C21 C22 C23 C18 0.1(4) . . . . yes C19 C18 C23 C22 0.6(4) . . . . yes C17 C18 C23 C22 -178.0(3) . . . . yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3B N1 0.85(4) 2.10(4) 2.941(3) 174(3) 1_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.178 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.050 data_18c _database_code_depnum_ccdc_archive 'CCDC 905363' #TrackingRef 'EJOC 10-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 04csf005 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H47 N1 O7' _chemical_formula_weight 653.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6749(8) _cell_length_b 11.6338(9) _cell_length_c 17.3660(11) _cell_angle_alpha 108.132(3) _cell_angle_beta 103.266(3) _cell_angle_gamma 110.833(4) _cell_volume 1769.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(1) _cell_measurement_reflns_used 6755 _cell_measurement_theta_min 2.227 _cell_measurement_theta_max 36.881 _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(1) _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 'Bruker Nonius Kappa Apex 2 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 36283 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.00 _reflns_number_total 8417 _reflns_number_gt 7356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0670P)^2^+0.7500P] 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 8417 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.96176(10) 0.40514(8) 0.20831(5) 0.02535(19) Uani 1 1 d . . . O2 O 0.78843(16) -0.21801(11) 0.02246(7) 0.0513(3) Uani 1 1 d . . . O3 O 0.74749(9) 0.61687(8) 0.39255(5) 0.02304(18) Uani 1 1 d . . . O4 O 0.61245(10) 0.17335(9) 0.53686(6) 0.0309(2) Uani 1 1 d . . . O5 O 0.41793(10) 0.48751(10) 0.26390(6) 0.0313(2) Uani 1 1 d . . . O6 O 0.53858(9) 0.36596(8) 0.23418(6) 0.02431(18) Uani 1 1 d . . . O7 O 0.37453(10) -0.25456(9) 0.06314(6) 0.0305(2) Uani 1 1 d . . . N1 N 1.16924(13) 1.03877(12) 0.44785(8) 0.0340(3) Uani 1 1 d . . . C1 C 1.11208(14) 0.77575(12) 0.26570(8) 0.0268(3) Uani 1 1 d . . . H1A H 1.1329 0.8270 0.2316 0.032 Uiso 1 1 calc R . . H1B H 1.2027 0.8055 0.3124 0.032 Uiso 1 1 calc R . . C2 C 1.05039(14) 0.62420(12) 0.20678(8) 0.0262(2) Uani 1 1 d . . . H2A H 0.9550 0.5934 0.1629 0.031 Uiso 1 1 calc R . . C3 C 1.03041(13) 0.54841(12) 0.26380(8) 0.0242(2) Uani 1 1 d . . . H3A H 1.1255 0.5751 0.3062 0.029 Uiso 1 1 calc R . . C4 C 0.93896(13) 0.58251(12) 0.31215(7) 0.0229(2) Uani 1 1 d . . . H4A H 0.8879 0.5196 0.3300 0.028 Uiso 1 1 calc R . . C5 C 0.92624(12) 0.69637(12) 0.33098(7) 0.0211(2) Uani 1 1 d . . . C6 C 0.81507(13) 0.71824(12) 0.36586(7) 0.0209(2) Uani 1 1 d . . . H6A H 0.8626 0.8081 0.4159 0.025 Uiso 1 1 calc R . . C7 C 0.69673(13) 0.71353(12) 0.29267(7) 0.0209(2) Uani 1 1 d . . . H7A H 0.6281 0.7318 0.3172 0.025 Uiso 1 1 calc R . . C8 C 0.76769(13) 0.82975(12) 0.26776(7) 0.0232(2) Uani 1 1 d . . . H8A H 0.6936 0.8148 0.2152 0.028 Uiso 1 1 calc R . . C9 C 0.89399(13) 0.82347(12) 0.24202(7) 0.0240(2) Uani 1 1 d . . . H9A H 0.9442 0.9061 0.2362 0.029 Uiso 1 1 calc R . . H9B H 0.8543 0.7475 0.1848 0.029 Uiso 1 1 calc R . . C10 C 1.00682(13) 0.80751(12) 0.30641(7) 0.0225(2) Uani 1 1 d . . . C11 C 0.61139(13) 0.56917(12) 0.21513(7) 0.0227(2) Uani 1 1 d . . . H11A H 0.6806 0.5370 0.2018 0.027 Uiso 1 1 calc R . . C12 C 0.51247(13) 0.47304(12) 0.24194(7) 0.0231(2) Uani 1 1 d . . . C13 C 1.14713(17) 0.59706(15) 0.15918(11) 0.0402(3) Uani 1 1 d . . . H13A H 1.2409 0.6261 0.2013 0.060 Uiso 1 1 calc R . . H13B H 1.1572 0.6467 0.1241 0.060 Uiso 1 1 calc R . . H13C H 1.1043 0.5013 0.1221 0.060 Uiso 1 1 calc R . . C14 C 0.80852(15) 0.96973(12) 0.33899(8) 0.0275(3) Uani 1 1 d . . . H14A H 0.8755 0.9858 0.3933 0.041 Uiso 1 1 calc R . . H14B H 0.7227 0.9712 0.3466 0.041 Uiso 1 1 calc R . . H14C H 0.8528 1.0396 0.3216 0.041 Uiso 1 1 calc R . . C15 C 0.51579(15) 0.56219(14) 0.13115(8) 0.0313(3) Uani 1 1 d . . . H15A H 0.4571 0.4687 0.0889 0.047 Uiso 1 1 calc R . . H15B H 0.5763 0.6115 0.1074 0.047 Uiso 1 1 calc R . . H15C H 0.4542 0.6020 0.1447 0.047 Uiso 1 1 calc R . . C16 C 1.09677(13) 0.93763(12) 0.38653(8) 0.0253(2) Uani 1 1 d . . . C17 C 0.9783(2) 0.32790(16) 0.25563(10) 0.0533(5) Uani 1 1 d . . . H17A H 0.9204 0.3278 0.2913 0.064 Uiso 1 1 calc R . . H17B H 1.0791 0.3686 0.2943 0.064 Uiso 1 1 calc R . . C18 C 0.93048(16) 0.18457(13) 0.19231(8) 0.0306(3) Uani 1 1 d . . . C19 C 1.02881(16) 0.14877(15) 0.16551(10) 0.0357(3) Uani 1 1 d . . . H19A H 1.1246 0.2148 0.1863 0.043 Uiso 1 1 calc R . . C20 C 0.98713(18) 0.01514(16) 0.10769(10) 0.0372(3) Uani 1 1 d . . . H20A H 1.0542 -0.0078 0.0900 0.045 Uiso 1 1 calc R . . C21 C 0.84449(17) -0.08241(13) 0.07724(8) 0.0317(3) Uani 1 1 d . . . C22 C 0.74518(15) -0.04706(14) 0.10276(8) 0.0305(3) Uani 1 1 d . . . H22A H 0.6491 -0.1126 0.0814 0.037 Uiso 1 1 calc R . . C23 C 0.78779(15) 0.08468(14) 0.15956(8) 0.0297(3) Uani 1 1 d . . . H23A H 0.7199 0.1073 0.1764 0.036 Uiso 1 1 calc R . . C24 C 0.8888(3) -0.2649(2) 0.00428(15) 0.0712(7) Uani 1 1 d . . . H24A H 0.9288 -0.2273 -0.0316 0.107 Uiso 1 1 calc R . . H24B H 0.8401 -0.3626 -0.0262 0.107 Uiso 1 1 calc R . . H24C H 0.9654 -0.2366 0.0583 0.107 Uiso 1 1 calc R . . C25 C 0.83366(14) 0.64519(13) 0.47924(7) 0.0258(2) Uani 1 1 d . . . H25A H 0.8327 0.7212 0.5224 0.031 Uiso 1 1 calc R . . H25B H 0.9333 0.6693 0.4851 0.031 Uiso 1 1 calc R . . C26 C 0.77133(13) 0.52019(12) 0.49413(7) 0.0227(2) Uani 1 1 d . . . C27 C 0.80880(13) 0.41548(13) 0.46588(8) 0.0242(2) Uani 1 1 d . . . H27A H 0.8723 0.4231 0.4368 0.029 Uiso 1 1 calc R . . C28 C 0.75336(13) 0.30095(12) 0.48030(8) 0.0243(2) Uani 1 1 d . . . H28A H 0.7799 0.2324 0.4614 0.029 Uiso 1 1 calc R . . C29 C 0.65739(13) 0.28826(12) 0.52338(8) 0.0234(2) Uani 1 1 d . . . C30 C 0.61596(13) 0.38964(13) 0.55039(8) 0.0261(2) Uani 1 1 d . . . H30A H 0.5501 0.3808 0.5778 0.031 Uiso 1 1 calc R . . C31 C 0.67440(14) 0.50464(13) 0.53579(8) 0.0254(2) Uani 1 1 d . . . H31A H 0.6476 0.5731 0.5545 0.030 Uiso 1 1 calc R . . C32 C 0.51878(15) 0.15970(15) 0.58409(10) 0.0342(3) Uani 1 1 d . . . H32A H 0.5663 0.2359 0.6408 0.051 Uiso 1 1 calc R . . H32B H 0.4963 0.0768 0.5909 0.051 Uiso 1 1 calc R . . H32C H 0.4308 0.1573 0.5523 0.051 Uiso 1 1 calc R . . C33 C 0.45955(14) 0.27328(13) 0.26543(8) 0.0274(3) Uani 1 1 d . . . H33A H 0.3673 0.2735 0.2605 0.033 Uiso 1 1 calc R . . H33B H 0.5148 0.3016 0.3266 0.033 Uiso 1 1 calc R . . C34 C 0.43506(13) 0.13311(12) 0.21073(8) 0.0241(2) Uani 1 1 d . . . C35 C 0.46781(13) 0.05369(13) 0.24910(8) 0.0256(2) Uani 1 1 d . . . H35 H 0.5061 0.0881 0.3099 0.031 Uiso 1 1 calc R . . C36 C 0.44448(14) -0.07578(13) 0.19838(8) 0.0266(3) Uani 1 1 d . . . H36 H 0.4662 -0.1280 0.2251 0.032 Uiso 1 1 calc R . . C37 C 0.38858(13) -0.12789(12) 0.10738(8) 0.0243(2) Uani 1 1 d . . . C38 C 0.35341(15) -0.05091(13) 0.06783(8) 0.0312(3) Uani 1 1 d . . . H38 H 0.3144 -0.0856 0.0070 0.037 Uiso 1 1 calc R . . C39 C 0.37703(15) 0.07859(14) 0.11989(8) 0.0319(3) Uani 1 1 d . . . H39 H 0.3533 0.1301 0.0932 0.038 Uiso 1 1 calc R . . C40 C 0.31722(19) -0.31171(15) -0.03008(9) 0.0421(4) Uani 1 1 d . . . H40A H 0.2222 -0.3185 -0.0507 0.063 Uiso 1 1 calc R . . H40B H 0.3111 -0.4009 -0.0533 0.063 Uiso 1 1 calc R . . H40C H 0.3797 -0.2543 -0.0491 0.063 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 0.0324(4) 0.0204(4) 0.0184(4) 0.0050(3) 0.0038(3) 0.0138(3) O2 0.0909(9) 0.0303(5) 0.0348(6) 0.0110(5) 0.0231(6) 0.0335(6) O3 0.0279(4) 0.0248(4) 0.0171(4) 0.0115(3) 0.0068(3) 0.0119(3) O4 0.0341(5) 0.0293(5) 0.0371(5) 0.0191(4) 0.0190(4) 0.0152(4) O5 0.0294(5) 0.0329(5) 0.0382(5) 0.0153(4) 0.0161(4) 0.0192(4) O6 0.0271(4) 0.0215(4) 0.0279(4) 0.0116(3) 0.0123(3) 0.0130(3) O7 0.0386(5) 0.0230(4) 0.0233(4) 0.0077(4) 0.0064(4) 0.0130(4) N1 0.0345(6) 0.0279(6) 0.0280(6) 0.0033(5) 0.0054(5) 0.0142(5) C1 0.0268(6) 0.0217(6) 0.0264(6) 0.0059(5) 0.0115(5) 0.0086(5) C2 0.0275(6) 0.0221(6) 0.0241(6) 0.0049(5) 0.0114(5) 0.0098(5) C3 0.0249(5) 0.0204(5) 0.0202(5) 0.0028(4) 0.0041(4) 0.0112(4) C4 0.0264(5) 0.0233(5) 0.0174(5) 0.0080(4) 0.0055(4) 0.0124(4) C5 0.0237(5) 0.0226(5) 0.0153(5) 0.0073(4) 0.0051(4) 0.0112(4) C6 0.0271(5) 0.0210(5) 0.0167(5) 0.0089(4) 0.0081(4) 0.0128(4) C7 0.0267(5) 0.0214(5) 0.0179(5) 0.0086(4) 0.0084(4) 0.0143(4) C8 0.0304(6) 0.0225(5) 0.0192(5) 0.0105(4) 0.0076(4) 0.0146(5) C9 0.0312(6) 0.0220(5) 0.0180(5) 0.0091(4) 0.0087(4) 0.0116(5) C10 0.0263(6) 0.0196(5) 0.0183(5) 0.0057(4) 0.0073(4) 0.0102(4) C11 0.0276(6) 0.0228(5) 0.0187(5) 0.0084(4) 0.0076(4) 0.0140(5) C12 0.0245(5) 0.0222(5) 0.0198(5) 0.0067(4) 0.0052(4) 0.0119(4) C13 0.0434(8) 0.0300(7) 0.0433(8) 0.0063(6) 0.0272(7) 0.0145(6) C14 0.0367(7) 0.0226(6) 0.0256(6) 0.0107(5) 0.0104(5) 0.0169(5) C15 0.0380(7) 0.0287(6) 0.0210(6) 0.0092(5) 0.0033(5) 0.0153(5) C16 0.0286(6) 0.0244(6) 0.0226(6) 0.0084(5) 0.0086(5) 0.0142(5) C17 0.0979(14) 0.0306(7) 0.0208(6) 0.0080(6) 0.0034(7) 0.0334(9) C18 0.0476(8) 0.0255(6) 0.0185(5) 0.0098(5) 0.0066(5) 0.0203(6) C19 0.0316(7) 0.0353(7) 0.0410(8) 0.0233(6) 0.0104(6) 0.0127(6) C20 0.0509(8) 0.0475(8) 0.0440(8) 0.0307(7) 0.0323(7) 0.0359(7) C21 0.0553(8) 0.0249(6) 0.0206(6) 0.0122(5) 0.0155(6) 0.0220(6) C22 0.0337(6) 0.0312(6) 0.0262(6) 0.0172(5) 0.0073(5) 0.0130(5) C23 0.0403(7) 0.0388(7) 0.0258(6) 0.0194(5) 0.0159(5) 0.0274(6) C24 0.142(2) 0.0569(11) 0.0643(13) 0.0344(10) 0.0701(15) 0.0703(14) C25 0.0325(6) 0.0262(6) 0.0165(5) 0.0102(5) 0.0060(5) 0.0126(5) C26 0.0260(5) 0.0258(6) 0.0153(5) 0.0097(4) 0.0046(4) 0.0123(5) C27 0.0251(5) 0.0305(6) 0.0193(5) 0.0115(5) 0.0096(4) 0.0140(5) C28 0.0264(6) 0.0265(6) 0.0217(5) 0.0096(5) 0.0089(4) 0.0149(5) C29 0.0234(5) 0.0254(6) 0.0209(5) 0.0116(5) 0.0066(4) 0.0106(5) C30 0.0264(6) 0.0344(6) 0.0236(6) 0.0146(5) 0.0119(5) 0.0171(5) C31 0.0304(6) 0.0301(6) 0.0205(5) 0.0115(5) 0.0093(5) 0.0188(5) C32 0.0310(6) 0.0368(7) 0.0364(7) 0.0205(6) 0.0164(6) 0.0113(6) C33 0.0307(6) 0.0260(6) 0.0284(6) 0.0132(5) 0.0138(5) 0.0132(5) C34 0.0226(5) 0.0228(5) 0.0241(6) 0.0104(5) 0.0071(4) 0.0085(4) C35 0.0259(6) 0.0263(6) 0.0196(5) 0.0106(5) 0.0051(4) 0.0086(5) C36 0.0295(6) 0.0254(6) 0.0235(6) 0.0136(5) 0.0057(5) 0.0114(5) C37 0.0232(5) 0.0207(5) 0.0228(6) 0.0086(5) 0.0052(4) 0.0069(4) C38 0.0398(7) 0.0272(6) 0.0186(6) 0.0098(5) 0.0025(5) 0.0125(5) C39 0.0407(7) 0.0279(6) 0.0248(6) 0.0138(5) 0.0045(5) 0.0163(5) C40 0.0556(9) 0.0305(7) 0.0245(7) 0.0035(6) 0.0048(6) 0.0173(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 O1 C17 1.4213(16) . yes O1 C3 1.4322(13) . yes O2 C21 1.3729(16) . yes O2 C24 1.417(2) . yes O3 C6 1.4194(14) . yes O3 C25 1.4357(13) . yes O4 C29 1.3646(15) . yes O4 C32 1.4292(16) . yes O5 C12 1.2041(15) . yes O6 C12 1.3444(14) . yes O6 C33 1.4478(15) . yes O7 C37 1.3673(15) . yes O7 C40 1.4224(16) . yes N1 C16 1.1452(17) . yes C1 C2 1.5269(16) . yes C1 C10 1.5479(17) . yes C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.5198(18) . yes C2 C13 1.5202(18) . yes C2 H2A 0.9800 . ? C3 C4 1.5032(17) . yes C3 H3A 0.9800 . ? C4 C5 1.3262(16) . yes C4 H4A 0.9300 . ? C5 C6 1.5129(16) . yes C5 C10 1.5213(16) . yes C6 C7 1.5444(15) . yes C6 H6A 0.9800 . ? C7 C8 1.5411(16) . yes C7 C11 1.5508(16) . yes C7 H7A 0.9800 . ? C8 C9 1.5327(17) . yes C8 C14 1.5381(16) . yes C8 H8A 0.9800 . ? C9 C10 1.5511(16) . yes C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C16 1.4803(16) . yes C11 C12 1.5141(17) . yes C11 C15 1.5361(16) . yes C11 H11A 0.9800 . ? 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 . ? C17 C18 1.4986(18) . yes C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.381(2) . yes C18 C23 1.388(2) . yes C19 C20 1.398(2) . yes C19 H19A 0.9300 . ? C20 C21 1.383(2) . yes C20 H20A 0.9300 . ? C21 C22 1.379(2) . yes C22 C23 1.3733(19) . yes C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.4997(17) . yes C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C31 1.3852(17) . yes C26 C27 1.3962(17) . yes C27 C28 1.3796(17) . yes C27 H27A 0.9300 . ? C28 C29 1.3941(17) . yes C28 H28A 0.9300 . ? C29 C30 1.3888(17) . yes C30 C31 1.3905(18) . yes C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.4996(17) . yes C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C39 1.3870(17) . yes C34 C35 1.3879(17) . yes C35 C36 1.3833(18) . yes C35 H35 0.9300 . ? C36 C37 1.3909(17) . yes C36 H36 0.9300 . ? C37 C38 1.3850(17) . yes C38 C39 1.3885(18) . yes C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 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 C17 O1 C3 112.56(10) . . yes C21 O2 C24 116.85(16) . . yes C6 O3 C25 112.27(9) . . yes C29 O4 C32 116.77(10) . . yes C12 O6 C33 116.63(9) . . yes C37 O7 C40 117.37(10) . . yes C2 C1 C10 112.50(10) . . yes C2 C1 H1A 109.1 . . ? C10 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? C10 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C13 112.00(11) . . yes C3 C2 C1 107.66(10) . . yes C13 C2 C1 111.73(11) . . yes C3 C2 H2A 108.5 . . ? C13 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? O1 C3 C4 110.40(10) . . yes O1 C3 C2 108.32(9) . . yes C4 C3 C2 110.09(10) . . yes O1 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C5 C4 C3 124.34(11) . . yes C5 C4 H4A 117.8 . . ? C3 C4 H4A 117.8 . . ? C4 C5 C6 123.25(11) . . yes C4 C5 C10 122.36(11) . . yes C6 C5 C10 113.78(9) . . yes O3 C6 C5 112.35(9) . . yes O3 C6 C7 108.39(9) . . yes C5 C6 C7 108.64(9) . . yes O3 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C8 C7 C6 108.73(9) . . yes C8 C7 C11 114.83(9) . . yes C6 C7 C11 110.50(9) . . yes C8 C7 H7A 107.5 . . ? C6 C7 H7A 107.5 . . ? C11 C7 H7A 107.5 . . ? C9 C8 C14 113.42(10) . . yes C9 C8 C7 111.79(9) . . yes C14 C8 C7 111.68(10) . . yes C9 C8 H8A 106.5 . . ? C14 C8 H8A 106.5 . . ? C7 C8 H8A 106.5 . . ? C8 C9 C10 115.82(9) . . yes C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C16 C10 C5 109.33(9) . . yes C16 C10 C1 106.55(10) . . yes C5 C10 C1 111.73(10) . . yes C16 C10 C9 109.57(10) . . yes C5 C10 C9 108.67(9) . . yes C1 C10 C9 110.96(10) . . yes C12 C11 C15 107.19(10) . . yes C12 C11 C7 109.04(9) . . yes C15 C11 C7 114.22(10) . . yes C12 C11 H11A 108.8 . . ? C15 C11 H11A 108.8 . . ? C7 C11 H11A 108.8 . . ? O5 C12 O6 124.08(11) . . yes O5 C12 C11 124.23(11) . . yes O6 C12 C11 111.62(10) . . yes C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C10 178.27(14) . . yes O1 C17 C18 109.36(11) . . yes O1 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? O1 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? C19 C18 C23 118.34(12) . . yes C19 C18 C17 120.28(15) . . yes C23 C18 C17 121.38(15) . . yes C18 C19 C20 121.25(13) . . yes C18 C19 H19A 119.4 . . ? C20 C19 H19A 119.4 . . ? C21 C20 C19 118.94(13) . . yes C21 C20 H20A 120.5 . . ? C19 C20 H20A 120.5 . . ? O2 C21 C22 114.14(13) . . yes O2 C21 C20 125.70(14) . . yes C22 C21 C20 120.15(12) . . yes C23 C22 C21 120.20(13) . . yes C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 C18 121.10(12) . . yes C22 C23 H23A 119.4 . . ? C18 C23 H23A 119.4 . . ? O2 C24 H24A 109.5 . . ? O2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 C26 108.46(9) . . yes O3 C25 H25A 110.0 . . ? C26 C25 H25A 110.0 . . ? O3 C25 H25B 110.0 . . ? C26 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C31 C26 C27 117.98(11) . . yes C31 C26 C25 121.15(11) . . yes C27 C26 C25 120.87(11) . . yes C28 C27 C26 121.22(11) . . yes C28 C27 H27A 119.4 . . ? C26 C27 H27A 119.4 . . ? C27 C28 C29 119.81(11) . . yes C27 C28 H28A 120.1 . . ? C29 C28 H28A 120.1 . . ? O4 C29 C30 124.71(11) . . yes O4 C29 C28 115.24(11) . . yes C30 C29 C28 120.05(11) . . yes C29 C30 C31 119.02(11) . . yes C29 C30 H30A 120.5 . . ? C31 C30 H30A 120.5 . . ? C26 C31 C30 121.89(11) . . yes C26 C31 H31A 119.1 . . ? C30 C31 H31A 119.1 . . ? O4 C32 H32A 109.5 . . ? O4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O6 C33 C34 108.22(10) . . yes O6 C33 H33A 110.1 . . ? C34 C33 H33A 110.1 . . ? O6 C33 H33B 110.1 . . ? C34 C33 H33B 110.1 . . ? H33A C33 H33B 108.4 . . ? C39 C34 C35 118.11(11) . . yes C39 C34 C33 120.61(11) . . yes C35 C34 C33 121.27(11) . . yes C36 C35 C34 121.08(11) . . yes C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C37 120.02(11) . . yes C35 C36 H36 120.0 . . ? C37 C36 H36 120.0 . . ? O7 C37 C38 124.61(11) . . yes O7 C37 C36 115.62(11) . . yes C38 C37 C36 119.76(11) . . yes C37 C38 C39 119.34(11) . . yes C37 C38 H38 120.3 . . ? C39 C38 H38 120.3 . . ? C34 C39 C38 121.68(11) . . yes C34 C39 H39 119.2 . . ? C38 C39 H39 119.2 . . ? O7 C40 H40A 109.5 . . ? O7 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O7 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 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 C10 C1 C2 C3 -63.24(13) . . . . yes C10 C1 C2 C13 173.40(12) . . . . yes C17 O1 C3 C4 -77.73(15) . . . . yes C17 O1 C3 C2 161.66(13) . . . . yes C13 C2 C3 O1 -61.38(13) . . . . yes C1 C2 C3 O1 175.42(9) . . . . yes C13 C2 C3 C4 177.82(10) . . . . yes C1 C2 C3 C4 54.62(13) . . . . yes O1 C3 C4 C5 -144.28(11) . . . . yes C2 C3 C4 C5 -24.74(16) . . . . yes C3 C4 C5 C6 169.39(10) . . . . yes C3 C4 C5 C10 -1.13(18) . . . . yes C25 O3 C6 C5 82.20(11) . . . . yes C25 O3 C6 C7 -157.74(9) . . . . yes C4 C5 C6 O3 11.92(15) . . . . yes C10 C5 C6 O3 -176.83(9) . . . . yes C4 C5 C6 C7 -108.00(12) . . . . yes C10 C5 C6 C7 63.25(12) . . . . yes O3 C6 C7 C8 176.13(9) . . . . yes C5 C6 C7 C8 -61.51(11) . . . . yes O3 C6 C7 C11 -56.98(12) . . . . yes C5 C6 C7 C11 65.37(12) . . . . yes C6 C7 C8 C9 55.04(12) . . . . yes C11 C7 C8 C9 -69.31(12) . . . . yes C6 C7 C8 C14 -73.24(12) . . . . yes C11 C7 C8 C14 162.40(10) . . . . yes C14 C8 C9 C10 78.26(12) . . . . yes C7 C8 C9 C10 -49.10(13) . . . . yes C4 C5 C10 C16 -122.74(12) . . . . yes C6 C5 C10 C16 65.91(12) . . . . yes C4 C5 C10 C1 -5.05(15) . . . . yes C6 C5 C10 C1 -176.40(9) . . . . yes C4 C5 C10 C9 117.70(12) . . . . yes C6 C5 C10 C9 -53.64(12) . . . . yes C2 C1 C10 C16 156.86(10) . . . . yes C2 C1 C10 C5 37.51(14) . . . . yes C2 C1 C10 C9 -83.93(13) . . . . yes C8 C9 C10 C16 -73.10(13) . . . . yes C8 C9 C10 C5 46.30(13) . . . . yes C8 C9 C10 C1 169.52(10) . . . . yes C8 C7 C11 C12 -163.26(10) . . . . yes C6 C7 C11 C12 73.32(12) . . . . yes C8 C7 C11 C15 -43.39(14) . . . . yes C6 C7 C11 C15 -166.81(10) . . . . yes C33 O6 C12 O5 -8.35(17) . . . . yes C33 O6 C12 C11 174.62(9) . . . . yes C15 C11 C12 O5 -64.14(15) . . . . yes C7 C11 C12 O5 59.99(15) . . . . yes C15 C11 C12 O6 112.88(11) . . . . yes C7 C11 C12 O6 -122.99(10) . . . . yes C5 C10 C16 N1 133(5) . . . . yes C1 C10 C16 N1 12(5) . . . . yes C9 C10 C16 N1 -108(5) . . . . yes C3 O1 C17 C18 -168.85(13) . . . . yes O1 C17 C18 C19 90.30(18) . . . . yes O1 C17 C18 C23 -90.06(18) . . . . yes C23 C18 C19 C20 -0.77(19) . . . . yes C17 C18 C19 C20 178.88(12) . . . . yes C18 C19 C20 C21 -0.1(2) . . . . yes C24 O2 C21 C22 -170.94(13) . . . . yes C24 O2 C21 C20 8.1(2) . . . . yes C19 C20 C21 O2 -178.01(12) . . . . yes C19 C20 C21 C22 1.0(2) . . . . yes O2 C21 C22 C23 178.15(11) . . . . yes C20 C21 C22 C23 -0.98(19) . . . . yes C21 C22 C23 C18 0.06(18) . . . . yes C19 C18 C23 C22 0.81(18) . . . . yes C17 C18 C23 C22 -178.83(12) . . . . yes C6 O3 C25 C26 -167.68(9) . . . . yes O3 C25 C26 C31 -95.25(13) . . . . yes O3 C25 C26 C27 84.39(13) . . . . yes C31 C26 C27 C28 -1.18(17) . . . . yes C25 C26 C27 C28 179.17(10) . . . . yes C26 C27 C28 C29 0.38(18) . . . . yes C32 O4 C29 C30 -1.54(18) . . . . yes C32 O4 C29 C28 177.46(11) . . . . yes C27 C28 C29 O4 -178.00(10) . . . . yes C27 C28 C29 C30 1.04(18) . . . . yes O4 C29 C30 C31 177.33(11) . . . . yes C28 C29 C30 C31 -1.62(18) . . . . yes C27 C26 C31 C30 0.58(18) . . . . yes C25 C26 C31 C30 -179.77(11) . . . . yes C29 C30 C31 C26 0.80(18) . . . . yes C12 O6 C33 C34 148.91(10) . . . . yes O6 C33 C34 C39 -50.35(15) . . . . yes O6 C33 C34 C35 130.47(12) . . . . yes C39 C34 C35 C36 0.52(19) . . . . yes C33 C34 C35 C36 179.73(11) . . . . yes C34 C35 C36 C37 0.60(19) . . . . yes C40 O7 C37 C38 -1.19(19) . . . . yes C40 O7 C37 C36 179.77(12) . . . . yes C35 C36 C37 O7 177.65(11) . . . . yes C35 C36 C37 C38 -1.44(19) . . . . yes O7 C37 C38 C39 -177.85(12) . . . . yes C36 C37 C38 C39 1.1(2) . . . . yes C35 C34 C39 C38 -0.8(2) . . . . yes C33 C34 C39 C38 179.97(13) . . . . yes C37 C38 C39 C34 0.0(2) . . . . yes _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.753 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.061 data_28a _database_code_depnum_ccdc_archive 'CCDC 905364' #TrackingRef 'EJOC 10-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H23 N O4, 0.5(C4 H8 O2)' _chemical_formula_sum 'C19 H27 N O5' _chemical_formula_weight 349.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 16.17422(15) _cell_length_b 16.17422(15) _cell_length_c 7.32793(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1917.03(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 9356 _cell_measurement_theta_min 2.7297 _cell_measurement_theta_max 71.3444 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28203 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 71.49 _reflns_number_total 3400 _reflns_number_gt 3022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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. Results of chirality/polarity tests _refine_ls_R_factor_obs+ 0.0374 _refine_ls_wR_factor_obs+ 0.0947 _refine_ls_abs_structure_Flack+ 0.0(2) _refine_ls_R_factor_obs- 0.0376 _refine_ls_wR_factor_obs- 0.0951 _refine_ls_abs_structure_Flack- 1.2(2) ; _chemical_absolute_configuration syn _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^)+(0.0616P)^2^+0.0234P] 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, 1390 Friedel pairs' _refine_ls_abs_structure_Flack -0.13(19) _refine_ls_number_reflns 3400 _refine_ls_number_parameters 203 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.47762(10) 0.20747(9) 0.5676(2) 0.0411(4) Uani 1 1 d . . . H1A H 0.4876 0.1841 0.4447 0.049 Uiso 1 1 calc R . . H1B H 0.4174 0.2053 0.5908 0.049 Uiso 1 1 calc R . . C2 C 0.50519(10) 0.29751(9) 0.5686(2) 0.0361(3) Uani 1 1 d . . . H2A H 0.5663 0.3001 0.5481 0.043 Uiso 1 1 calc R . . C3 C 0.48528(9) 0.33248(9) 0.7564(2) 0.0353(3) Uani 1 1 d . . . H3A H 0.4239 0.3340 0.7723 0.042 Uiso 1 1 calc R . . C4 C 0.52213(9) 0.27953(9) 0.9041(2) 0.0373(3) Uani 1 1 d . . . H4A H 0.5337 0.3048 1.0183 0.045 Uiso 1 1 calc R . . C5 C 0.53949(10) 0.19998(9) 0.8855(2) 0.0375(3) Uani 1 1 d . . . C6 C 0.58305(12) 0.14962(10) 1.0287(3) 0.0444(4) Uani 1 1 d . . . H6A H 0.5443 0.1066 1.0764 0.053 Uiso 1 1 calc R . . C7 C 0.66242(12) 0.10752(10) 0.9612(3) 0.0493(4) Uani 1 1 d . . . H7A H 0.6744 0.0612 1.0475 0.059 Uiso 1 1 calc R . . C8 C 0.65817(12) 0.06982(11) 0.7686(3) 0.0521(4) Uani 1 1 d . . . H8A H 0.7159 0.0695 0.7200 0.063 Uiso 1 1 calc R . . C9 C 0.60596(11) 0.12020(10) 0.6339(3) 0.0455(4) Uani 1 1 d . . . H9A H 0.5944 0.0853 0.5258 0.055 Uiso 1 1 calc R . . H9B H 0.6391 0.1680 0.5921 0.055 Uiso 1 1 calc R . . C10 C 0.52211(11) 0.15296(9) 0.7103(2) 0.0412(4) Uani 1 1 d . . . C11 C 0.46136(11) 0.34514(10) 0.4170(3) 0.0452(4) Uani 1 1 d . . . H11A H 0.4797 0.4029 0.4183 0.068 Uiso 1 1 calc R . . H11B H 0.4015 0.3429 0.4367 0.068 Uiso 1 1 calc R . . H11C H 0.4747 0.3202 0.2987 0.068 Uiso 1 1 calc R . . O12 O 0.51714(7) 0.41491(6) 0.77298(15) 0.0380(3) Uani 1 1 d D . . H12 H 0.4884(11) 0.4421(11) 0.859(2) 0.051(5) Uiso 1 1 d D . . O13 O 0.61004(9) 0.20169(7) 1.17853(18) 0.0534(3) Uani 1 1 d . . . C14 C 0.69147(15) 0.21736(11) 1.1614(3) 0.0587(5) Uani 1 1 d . . . O14 O 0.72745(12) 0.26014(9) 1.2721(3) 0.0794(5) Uani 1 1 d . . . C15 C 0.72746(12) 0.17394(11) 0.9950(3) 0.0563(5) Uani 1 1 d . . . O16 O 0.72456(8) 0.22822(8) 0.8409(2) 0.0590(4) Uani 1 1 d . . . C17 C 0.77080(17) 0.30256(15) 0.8503(5) 0.0842(8) Uani 1 1 d . . . H17A H 0.7632 0.3340 0.7372 0.126 Uiso 1 1 calc R . . H17B H 0.8295 0.2894 0.8660 0.126 Uiso 1 1 calc R . . H17C H 0.7516 0.3356 0.9541 0.126 Uiso 1 1 calc R . . C18 C 0.81399(15) 0.14068(16) 1.0288(5) 0.0808(8) Uani 1 1 d . . . H18A H 0.8520 0.1869 1.0497 0.121 Uiso 1 1 calc R . . H18B H 0.8323 0.1090 0.9222 0.121 Uiso 1 1 calc R . . H18C H 0.8134 0.1047 1.1364 0.121 Uiso 1 1 calc R . . C19 C 0.63052(16) -0.02106(11) 0.7805(4) 0.0686(6) Uani 1 1 d . . . H19A H 0.6286 -0.0449 0.6576 0.103 Uiso 1 1 calc R . . H19B H 0.5754 -0.0240 0.8359 0.103 Uiso 1 1 calc R . . H19C H 0.6699 -0.0522 0.8555 0.103 Uiso 1 1 calc R . . C20 C 0.46558(12) 0.08364(10) 0.7504(3) 0.0497(4) Uani 1 1 d . . . N21 N 0.41812(12) 0.03222(10) 0.7798(3) 0.0658(5) 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 0.0475(8) 0.0369(8) 0.0389(9) -0.0013(7) -0.0040(7) -0.0019(6) C2 0.0404(8) 0.0338(7) 0.0341(9) -0.0019(6) 0.0019(7) -0.0016(6) C3 0.0373(7) 0.0321(7) 0.0363(9) 0.0009(6) 0.0048(7) -0.0015(6) C4 0.0435(8) 0.0379(8) 0.0306(8) -0.0009(6) 0.0042(7) -0.0015(6) C5 0.0430(8) 0.0355(7) 0.0340(9) 0.0015(6) 0.0036(7) -0.0009(6) C6 0.0626(10) 0.0347(8) 0.0360(9) 0.0019(7) -0.0014(8) 0.0007(7) C7 0.0641(11) 0.0361(8) 0.0476(11) 0.0031(7) -0.0042(8) 0.0070(7) C8 0.0631(11) 0.0434(9) 0.0498(11) -0.0035(8) 0.0002(9) 0.0111(8) C9 0.0582(10) 0.0385(8) 0.0399(10) -0.0044(7) 0.0063(8) 0.0043(7) C10 0.0516(9) 0.0326(8) 0.0393(9) 0.0008(7) 0.0001(7) -0.0029(6) C11 0.0567(10) 0.0406(8) 0.0383(9) 0.0021(7) -0.0065(8) -0.0024(7) O12 0.0437(6) 0.0315(5) 0.0390(6) -0.0004(5) 0.0061(5) -0.0011(4) O13 0.0757(9) 0.0458(7) 0.0386(7) 0.0004(5) -0.0096(6) 0.0038(6) C14 0.0819(14) 0.0408(9) 0.0533(12) 0.0038(9) -0.0200(11) 0.0010(9) O14 0.1027(12) 0.0607(8) 0.0748(12) -0.0100(8) -0.0363(10) -0.0013(8) C15 0.0597(11) 0.0454(9) 0.0637(13) 0.0029(9) -0.0160(10) 0.0049(8) O16 0.0564(7) 0.0518(7) 0.0687(10) 0.0121(7) -0.0072(7) -0.0053(6) C17 0.0889(17) 0.0630(13) 0.101(2) 0.0051(14) 0.0022(16) -0.0191(12) C18 0.0681(13) 0.0730(14) 0.101(2) -0.0011(15) -0.0237(14) 0.0153(11) C19 0.1031(17) 0.0392(9) 0.0634(14) -0.0064(9) -0.0113(13) 0.0177(10) C20 0.0703(12) 0.0360(8) 0.0429(10) -0.0014(8) -0.0035(9) -0.0056(8) N21 0.0866(12) 0.0499(9) 0.0609(11) 0.0061(8) -0.0042(10) -0.0242(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 C1 C2 1.523(2) . ? C1 C10 1.546(2) . ? C2 C3 1.523(2) . ? C2 C11 1.526(2) . ? C3 O12 1.4345(17) . ? C3 C4 1.503(2) . ? C4 C5 1.324(2) . ? C5 C6 1.504(2) . ? C5 C10 1.518(2) . ? C6 O13 1.451(2) . ? C6 C7 1.535(3) . ? C7 C15 1.524(3) . ? C7 C8 1.539(3) . ? C8 C9 1.534(3) . ? C8 C19 1.539(3) . ? C9 C10 1.560(2) . ? C10 C20 1.476(2) . ? O13 C14 1.347(3) . ? C14 O14 1.215(2) . ? C14 C15 1.523(3) . ? C15 O16 1.431(3) . ? C15 C18 1.520(3) . ? O16 C17 1.418(3) . ? C20 N21 1.152(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.96(13) . . ? C3 C2 C1 107.30(12) . . ? C3 C2 C11 111.85(13) . . ? C1 C2 C11 110.08(13) . . ? O12 C3 C4 109.04(13) . . ? O12 C3 C2 110.22(12) . . ? C4 C3 C2 110.81(12) . . ? C5 C4 C3 124.32(15) . . ? C4 C5 C6 123.65(15) . . ? C4 C5 C10 122.31(15) . . ? C6 C5 C10 113.91(13) . . ? O13 C6 C5 110.76(12) . . ? O13 C6 C7 104.46(15) . . ? C5 C6 C7 114.04(15) . . ? C15 C7 C6 102.26(15) . . ? C15 C7 C8 117.33(18) . . ? C6 C7 C8 115.72(16) . . ? C9 C8 C7 113.85(14) . . ? C9 C8 C19 112.56(17) . . ? C7 C8 C19 109.87(17) . . ? C8 C9 C10 115.34(15) . . ? C20 C10 C5 109.08(14) . . ? C20 C10 C1 106.23(14) . . ? C5 C10 C1 111.87(13) . . ? C20 C10 C9 110.61(13) . . ? C5 C10 C9 108.22(14) . . ? C1 C10 C9 110.82(14) . . ? C14 O13 C6 109.44(15) . . ? O14 C14 O13 120.9(2) . . ? O14 C14 C15 127.9(2) . . ? O13 C14 C15 111.20(16) . . ? O16 C15 C18 112.1(2) . . ? O16 C15 C14 109.65(14) . . ? C18 C15 C14 112.6(2) . . ? O16 C15 C7 106.36(16) . . ? C18 C15 C7 114.38(17) . . ? C14 C15 C7 101.03(17) . . ? C17 O16 C15 117.69(19) . . ? N21 C20 C10 176.5(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 71.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.109 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.028 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.038 415 102 ' ' _platon_squeeze_details ; SQUEEZE suggested 102 e/cell = 25.5 e/asu The solvents used were thf (C4H8O, 40e) in the preparation, and ethyl acetate (C4H8O2, 48e) and hexane (C6H14, 60e) in the recrystallisation. Before SQUEEZE, the solvent looked like ethyl acetate 0.5EtOAc = 24e, so this was used as the solvent present. So, the atom list is low by 0.5(C4 H8 O2) = C2 H4 O, and the UNIT is low by C8 H16 O4, i.e. C68 H92 N4 O16 ; data_31 _database_code_depnum_ccdc_archive 'CCDC 905365' #TrackingRef 'EJOC 10-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H29 N O6' _chemical_formula_sum 'C19 H29 N O6' _chemical_formula_weight 367.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6847(2) _cell_length_b 12.1746(3) _cell_length_c 14.6780(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.328(2) _cell_angle_gamma 90.00 _cell_volume 1901.09(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16759 _cell_measurement_theta_min 3.0170 _cell_measurement_theta_max 72.4662 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.784 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28509 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 72.55 _reflns_number_total 3756 _reflns_number_gt 3397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.0533P)^2^+0.4969P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3756 _refine_ls_number_parameters 243 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C1 C 0.93227(11) 0.59413(11) 0.39407(9) 0.0333(3) Uani 1 1 d . . . H1A H 0.9728 0.5299 0.4260 0.040 Uiso 1 1 calc R . . H1B H 0.9999 0.6404 0.3727 0.040 Uiso 1 1 calc R . . C2 C 0.86471(12) 0.66051(11) 0.46358(9) 0.0340(3) Uani 1 1 d . . . H2A H 0.9248 0.6649 0.5199 0.041 Uiso 1 1 calc R . . C3 C 0.75003(11) 0.59758(10) 0.49175(8) 0.0296(3) Uani 1 1 d . . . H3A H 0.6997 0.6484 0.5276 0.036 Uiso 1 1 calc R . . C4 C 0.66365(11) 0.55237(10) 0.41087(8) 0.0260(2) Uani 1 1 d . . . H4A H 0.6002 0.5025 0.4351 0.031 Uiso 1 1 calc R . . C5 C 0.73341(11) 0.48920(9) 0.34071(8) 0.0260(3) Uani 1 1 d . . . C6 C 0.64977(11) 0.45166(9) 0.25558(8) 0.0259(2) Uani 1 1 d . . . H6A H 0.6414 0.5096 0.2071 0.031 Uiso 1 1 calc R . . C7 C 0.72809(12) 0.35319(10) 0.22785(8) 0.0284(3) Uani 1 1 d . . . H7A H 0.6777 0.3041 0.1838 0.034 Uiso 1 1 calc R . . C8 C 0.84814(13) 0.39443(11) 0.18768(9) 0.0338(3) Uani 1 1 d . . . H8A H 0.9016 0.3283 0.1799 0.041 Uiso 1 1 calc R . . C9 C 0.92593(12) 0.47187(11) 0.25418(9) 0.0338(3) Uani 1 1 d . . . H9A H 0.9826 0.5155 0.2186 0.041 Uiso 1 1 calc R . . H9B H 0.9794 0.4264 0.2981 0.041 Uiso 1 1 calc R . . C10 C 0.84918(11) 0.55239(10) 0.30941(9) 0.0295(3) Uani 1 1 d . . . C11 C 0.83459(15) 0.77964(12) 0.43585(11) 0.0422(3) Uani 1 1 d . . . H11A H 0.7916 0.8157 0.4839 0.063 Uiso 1 1 calc R . . H11B H 0.7800 0.7806 0.3784 0.063 Uiso 1 1 calc R . . H11C H 0.9128 0.8188 0.4275 0.063 Uiso 1 1 calc R . . O12 O 0.79920(8) 0.51204(8) 0.55133(6) 0.0325(2) Uani 1 1 d . . . C13 C 0.70813(14) 0.45489(14) 0.59697(10) 0.0428(3) Uani 1 1 d . . . H13A H 0.6453 0.5069 0.6155 0.064 Uiso 1 1 calc R . . H13B H 0.7491 0.4183 0.6513 0.064 Uiso 1 1 calc R . . H13C H 0.6669 0.3998 0.5557 0.064 Uiso 1 1 calc R . . O14 O 0.60002(8) 0.64471(7) 0.36875(6) 0.0311(2) Uani 1 1 d D . . H14 H 0.5494(15) 0.6209(16) 0.3204(8) 0.055(5) Uiso 1 1 d D . . O15 O 0.77995(8) 0.38812(6) 0.38425(6) 0.0267(2) Uani 1 1 d . . . C16 C 0.75440(11) 0.29817(10) 0.32205(8) 0.0277(3) Uani 1 1 d . . . C17 C 0.63785(12) 0.23284(9) 0.34388(8) 0.0284(3) Uani 1 1 d . . . O17 O 0.58464(9) 0.16856(7) 0.29058(6) 0.0352(2) Uani 1 1 d . . . O18 O 0.60955(9) 0.24682(7) 0.42952(6) 0.0323(2) Uani 1 1 d . . . C19 C 0.50203(14) 0.18498(12) 0.45409(10) 0.0405(3) Uani 1 1 d . . . H19A H 0.4306 0.1977 0.4085 0.061 Uiso 1 1 calc R . . H19B H 0.4800 0.2088 0.5144 0.061 Uiso 1 1 calc R . . H19C H 0.5226 0.1065 0.4561 0.061 Uiso 1 1 calc R . . C20 C 0.86412(13) 0.21727(11) 0.33453(10) 0.0357(3) Uani 1 1 d . . . H20A H 0.9419 0.2545 0.3216 0.054 Uiso 1 1 calc R . . H20B H 0.8482 0.1554 0.2923 0.054 Uiso 1 1 calc R . . H20C H 0.8726 0.1901 0.3976 0.054 Uiso 1 1 calc R . . O21 O 0.53152(7) 0.42063(7) 0.28429(6) 0.0278(2) Uani 1 1 d . . . C22 C 0.43879(13) 0.39645(11) 0.21068(9) 0.0340(3) Uani 1 1 d . . . H22A H 0.4268 0.4606 0.1705 0.051 Uiso 1 1 calc R . . H22B H 0.3592 0.3782 0.2353 0.051 Uiso 1 1 calc R . . H22C H 0.4667 0.3339 0.1757 0.051 Uiso 1 1 calc R . . C23 C 0.81682(15) 0.44307(13) 0.09181(10) 0.0438(3) Uani 1 1 d . . . H23A H 0.7670 0.3901 0.0535 0.066 Uiso 1 1 calc R . . H23B H 0.8949 0.4592 0.0643 0.066 Uiso 1 1 calc R . . H23C H 0.7685 0.5109 0.0964 0.066 Uiso 1 1 calc R . . C24 C 0.81028(12) 0.64556(11) 0.24830(9) 0.0321(3) Uani 1 1 d . . . N25 N 0.78917(12) 0.71607(10) 0.19746(9) 0.0419(3) 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 0.0237(6) 0.0334(6) 0.0425(7) 0.0028(5) 0.0021(5) -0.0013(5) C2 0.0295(6) 0.0336(7) 0.0379(6) -0.0024(5) -0.0014(5) -0.0039(5) C3 0.0277(6) 0.0302(6) 0.0305(6) -0.0013(5) 0.0007(5) 0.0020(5) C4 0.0236(5) 0.0242(5) 0.0304(6) 0.0004(4) 0.0036(4) 0.0024(4) C5 0.0255(5) 0.0218(5) 0.0311(6) 0.0012(4) 0.0049(4) 0.0013(4) C6 0.0261(5) 0.0234(5) 0.0290(6) 0.0006(4) 0.0070(4) -0.0001(4) C7 0.0321(6) 0.0253(6) 0.0288(6) -0.0018(5) 0.0073(5) 0.0022(5) C8 0.0367(7) 0.0317(6) 0.0351(6) -0.0006(5) 0.0151(5) 0.0042(5) C9 0.0286(6) 0.0331(6) 0.0416(7) 0.0020(5) 0.0137(5) 0.0020(5) C10 0.0254(6) 0.0275(6) 0.0366(6) 0.0006(5) 0.0079(5) 0.0004(5) C11 0.0431(8) 0.0309(7) 0.0528(8) -0.0052(6) 0.0048(6) -0.0059(6) O12 0.0272(4) 0.0382(5) 0.0320(4) 0.0046(4) 0.0020(3) 0.0031(4) C13 0.0407(7) 0.0531(8) 0.0356(7) 0.0098(6) 0.0081(6) -0.0005(6) O14 0.0292(4) 0.0257(4) 0.0376(5) -0.0008(3) -0.0014(4) 0.0055(3) O15 0.0282(4) 0.0211(4) 0.0309(4) -0.0004(3) 0.0037(3) 0.0036(3) C16 0.0304(6) 0.0224(5) 0.0310(6) -0.0014(4) 0.0067(5) 0.0026(5) C17 0.0332(6) 0.0205(5) 0.0318(6) 0.0010(4) 0.0055(5) 0.0042(4) O17 0.0440(5) 0.0256(4) 0.0364(5) -0.0038(4) 0.0056(4) -0.0035(4) O18 0.0359(5) 0.0306(4) 0.0313(4) 0.0001(3) 0.0086(4) -0.0028(4) C19 0.0400(7) 0.0400(7) 0.0435(7) 0.0016(6) 0.0150(6) -0.0056(6) C20 0.0369(7) 0.0277(6) 0.0432(7) -0.0003(5) 0.0077(5) 0.0091(5) O21 0.0244(4) 0.0281(4) 0.0313(4) -0.0028(3) 0.0045(3) -0.0027(3) C22 0.0333(6) 0.0302(6) 0.0374(6) -0.0039(5) -0.0022(5) -0.0032(5) C23 0.0521(8) 0.0471(8) 0.0348(7) 0.0015(6) 0.0173(6) -0.0001(7) C24 0.0271(6) 0.0304(6) 0.0399(7) 0.0001(5) 0.0087(5) -0.0029(5) N25 0.0418(6) 0.0385(6) 0.0464(7) 0.0096(5) 0.0089(5) 0.0002(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 C1 C2 1.5336(19) . ? C1 C10 1.5446(18) . ? C2 C11 1.532(2) . ? C2 C3 1.5341(18) . ? C3 O12 1.4283(15) . ? C3 C4 1.5364(16) . ? C4 O14 1.4248(14) . ? C4 C5 1.5330(16) . ? C5 O15 1.4529(14) . ? C5 C6 1.5367(17) . ? C5 C10 1.5616(16) . ? C6 O21 1.4197(14) . ? C6 C7 1.5384(16) . ? C7 C16 1.5387(17) . ? C7 C8 1.5444(17) . ? C8 C23 1.5347(19) . ? C8 C9 1.5433(19) . ? C9 C10 1.5537(17) . ? C10 C24 1.4814(18) . ? O12 C13 1.4145(17) . ? O15 C16 1.4356(14) . ? C16 C20 1.5292(17) . ? C16 C17 1.5362(17) . ? C17 O17 1.2105(16) . ? C17 O18 1.3308(15) . ? O18 C19 1.4469(16) . ? O21 C22 1.4272(15) . ? C24 N25 1.1461(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 115.96(10) . . ? C11 C2 C1 114.97(12) . . ? C11 C2 C3 113.02(11) . . ? C1 C2 C3 110.68(10) . . ? O12 C3 C2 105.76(10) . . ? O12 C3 C4 111.86(10) . . ? C2 C3 C4 114.09(10) . . ? O14 C4 C5 110.28(9) . . ? O14 C4 C3 106.31(9) . . ? C5 C4 C3 113.83(10) . . ? O15 C5 C4 107.30(9) . . ? O15 C5 C6 104.79(9) . . ? C4 C5 C6 114.40(9) . . ? O15 C5 C10 107.37(9) . . ? C4 C5 C10 113.47(10) . . ? C6 C5 C10 108.90(9) . . ? O21 C6 C5 107.71(9) . . ? O21 C6 C7 113.09(10) . . ? C5 C6 C7 99.05(9) . . ? C6 C7 C16 99.20(9) . . ? C6 C7 C8 109.83(10) . . ? C16 C7 C8 113.31(10) . . ? C23 C8 C9 113.76(11) . . ? C23 C8 C7 110.94(11) . . ? C9 C8 C7 112.01(10) . . ? C8 C9 C10 115.85(10) . . ? C24 C10 C1 110.08(10) . . ? C24 C10 C9 107.41(10) . . ? C1 C10 C9 109.60(10) . . ? C24 C10 C5 111.72(10) . . ? C1 C10 C5 109.70(10) . . ? C9 C10 C5 108.27(10) . . ? C13 O12 C3 114.74(10) . . ? C16 O15 C5 109.22(8) . . ? O15 C16 C20 108.47(10) . . ? O15 C16 C17 111.86(9) . . ? C20 C16 C17 105.59(10) . . ? O15 C16 C7 104.33(9) . . ? C20 C16 C7 117.52(10) . . ? C17 C16 C7 109.20(10) . . ? O17 C17 O18 123.98(11) . . ? O17 C17 C16 122.76(11) . . ? O18 C17 C16 112.99(10) . . ? C17 O18 C19 115.10(10) . . ? C6 O21 C22 113.86(9) . . ? N25 C24 C10 174.24(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 72.55 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.349 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.037 #===END