# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Andrew J.P. White' _publ_contact_author_email a.white@imperial.ac.uk loop_ _publ_author_name 'Helmut Haning' 'Carles Giro Manas' 'Victoria Paddock' 'Christian Bochet' 'Andrew J.P. White' ; G.Bernardinelli ; 'Inderjit Mann' 'Wolfang Oppolzer' 'Alan C. Spivey' data_13 _database_code_depnum_ccdc_archive 'CCDC 792816' #TrackingRef 'OBC 08-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O6' _chemical_formula_weight 362.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 14.5941(4) _cell_length_b 9.4049(2) _cell_length_c 13.8121(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.949(2) _cell_angle_gamma 90.00 _cell_volume 1894.70(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7620 _cell_measurement_theta_min 3.7841 _cell_measurement_theta_max 31.8391 _exptl_crystal_description plates _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81049 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29265 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 31.97 _reflns_number_total 6105 _reflns_number_gt 3310 _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^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6105 _refine_ls_number_parameters 235 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.981 _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 0.23622(6) 0.48195(10) 0.34081(6) 0.0363(2) Uani 1 1 d . . . C2 C 0.20751(10) 0.35694(15) 0.28950(11) 0.0419(3) Uani 1 1 d . . . H2A H 0.1564 0.3109 0.3229 0.050 Uiso 1 1 calc R . . H2B H 0.1859 0.3822 0.2230 0.050 Uiso 1 1 calc R . . O3 O 0.28333(6) 0.26235(10) 0.28603(7) 0.0417(3) Uani 1 1 d . . . C4 C 0.35871(9) 0.34124(13) 0.31617(8) 0.0291(3) Uani 1 1 d . . . C5 C 0.44902(9) 0.30155(13) 0.31716(9) 0.0302(3) Uani 1 1 d . . . H5A H 0.4670 0.2102 0.2953 0.036 Uiso 1 1 calc R . . C6 C 0.51428(8) 0.40117(13) 0.35178(8) 0.0267(3) Uani 1 1 d . . . C7 C 0.48397(9) 0.53278(13) 0.38530(8) 0.0302(3) Uani 1 1 d . . . H7A H 0.5281 0.5990 0.4098 0.036 Uiso 1 1 calc R . . C8 C 0.39183(9) 0.57071(13) 0.38418(9) 0.0318(3) Uani 1 1 d . . . H8A H 0.3724 0.6606 0.4072 0.038 Uiso 1 1 calc R . . C9 C 0.33062(8) 0.47241(13) 0.34837(8) 0.0283(3) Uani 1 1 d . . . C10 C 0.61366(8) 0.36849(13) 0.35555(8) 0.0278(3) Uani 1 1 d . . . C11 C 0.64251(9) 0.21589(13) 0.36733(8) 0.0299(3) Uani 1 1 d . . . H11A H 0.6116 0.1570 0.3155 0.036 Uiso 1 1 calc R . . O12 O 0.61865(6) 0.16293(9) 0.46073(6) 0.0340(2) Uani 1 1 d . . . C13 C 0.67538(11) 0.04181(14) 0.48021(9) 0.0392(3) Uani 1 1 d . . . O14 O 0.75458(7) 0.05978(10) 0.42116(7) 0.0426(3) Uani 1 1 d . . . C15 C 0.74504(9) 0.18972(14) 0.36780(9) 0.0340(3) Uani 1 1 d . . . H15A H 0.7649 0.1749 0.3000 0.041 Uiso 1 1 calc R . . C16 C 0.79892(9) 0.31139(14) 0.41401(9) 0.0351(3) Uani 1 1 d . . . H16A H 0.8653 0.2903 0.4126 0.042 Uiso 1 1 calc R . . H16B H 0.7823 0.3215 0.4826 0.042 Uiso 1 1 calc R . . C17 C 0.77875(9) 0.45059(14) 0.36006(9) 0.0333(3) Uani 1 1 d . . . H17A H 0.8062 0.4451 0.2948 0.040 Uiso 1 1 calc R . . C18 C 0.67700(9) 0.46934(14) 0.34641(9) 0.0319(3) Uani 1 1 d . . . H18A H 0.6557 0.5619 0.3296 0.038 Uiso 1 1 calc R . . C19 C 0.62691(11) -0.09388(15) 0.45118(11) 0.0482(4) Uani 1 1 d . . . H19A H 0.6101 -0.0907 0.3819 0.072 Uiso 1 1 calc R . . H19B H 0.5714 -0.1043 0.4885 0.072 Uiso 1 1 calc R . . H19C H 0.6677 -0.1749 0.4642 0.072 Uiso 1 1 calc R . . C20 C 0.70396(14) 0.04564(18) 0.58658(11) 0.0614(5) Uani 1 1 d . . . H20A H 0.7349 0.1359 0.6014 0.092 Uiso 1 1 calc R . . H20B H 0.7459 -0.0334 0.6013 0.092 Uiso 1 1 calc R . . H20C H 0.6496 0.0369 0.6258 0.092 Uiso 1 1 calc R . . C21 C 0.81924(9) 0.57986(14) 0.41400(10) 0.0372(3) Uani 1 1 d . . . H21A H 0.7903 0.6671 0.3869 0.045 Uiso 1 1 calc R . . H21B H 0.8034 0.5736 0.4830 0.045 Uiso 1 1 calc R . . C22 C 0.92117(11) 0.59338(16) 0.40833(12) 0.0506(4) Uani 1 1 d . . . H22A H 0.9485 0.4962 0.4149 0.061 Uiso 1 1 calc R . . O23 O 0.93898(7) 0.64482(13) 0.31497(9) 0.0607(3) Uani 1 1 d . . . C24 C 1.03410(14) 0.6367(3) 0.2906(2) 0.1164(10) Uani 1 1 d U . . H24A H 1.0432 0.6879 0.2298 0.175 Uiso 1 1 calc R . . H24B H 1.0516 0.5369 0.2828 0.175 Uiso 1 1 calc R . . H24C H 1.0722 0.6798 0.3425 0.175 Uiso 1 1 calc R . . O25 O 0.96150(9) 0.68073(12) 0.48154(10) 0.0726(4) Uani 1 1 d U . . C26 C 0.93115(16) 0.8238(2) 0.48088(17) 0.0857(7) Uani 1 1 d U . . H26A H 0.9541 0.8717 0.5399 0.129 Uiso 1 1 calc R . . H26B H 0.8640 0.8262 0.4783 0.129 Uiso 1 1 calc R . . H26C H 0.9544 0.8726 0.4240 0.129 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 0.0329(5) 0.0358(5) 0.0401(5) -0.0046(4) -0.0006(4) 0.0041(4) C2 0.0357(8) 0.0371(8) 0.0526(8) -0.0082(7) -0.0019(6) 0.0010(6) O3 0.0341(5) 0.0306(5) 0.0597(6) -0.0081(4) -0.0068(4) 0.0001(4) C4 0.0348(7) 0.0255(6) 0.0267(6) 0.0008(5) -0.0022(5) -0.0022(5) C5 0.0363(7) 0.0227(6) 0.0314(6) -0.0024(5) -0.0009(5) 0.0035(5) C6 0.0327(7) 0.0252(6) 0.0221(5) 0.0023(5) -0.0003(5) 0.0013(5) C7 0.0382(7) 0.0261(6) 0.0263(6) -0.0014(5) -0.0017(5) -0.0027(5) C8 0.0416(8) 0.0248(6) 0.0291(6) -0.0040(5) 0.0003(5) 0.0042(6) C9 0.0318(7) 0.0283(6) 0.0247(6) 0.0009(5) 0.0018(5) 0.0041(5) C10 0.0338(7) 0.0282(6) 0.0212(5) 0.0001(5) -0.0003(5) 0.0016(5) C11 0.0367(7) 0.0301(7) 0.0230(6) -0.0032(5) 0.0018(5) 0.0019(5) O12 0.0494(6) 0.0246(5) 0.0283(4) 0.0014(4) 0.0061(4) 0.0066(4) C13 0.0578(9) 0.0267(7) 0.0332(7) -0.0002(6) 0.0030(6) 0.0102(6) O14 0.0447(6) 0.0312(5) 0.0518(6) 0.0019(4) 0.0007(5) 0.0103(4) C15 0.0384(7) 0.0308(7) 0.0328(7) -0.0007(5) 0.0011(5) 0.0062(6) C16 0.0336(7) 0.0346(7) 0.0369(7) 0.0015(6) -0.0027(5) 0.0059(6) C17 0.0329(7) 0.0369(7) 0.0299(6) 0.0028(5) 0.0009(5) 0.0002(6) C18 0.0347(7) 0.0323(7) 0.0284(6) 0.0052(5) -0.0014(5) 0.0025(6) C19 0.0644(11) 0.0272(7) 0.0536(9) -0.0028(6) 0.0114(7) 0.0034(7) C20 0.1031(15) 0.0421(9) 0.0380(8) 0.0024(7) -0.0102(8) 0.0203(9) C21 0.0415(8) 0.0328(7) 0.0369(7) 0.0060(6) -0.0052(6) -0.0016(6) C22 0.0410(9) 0.0357(8) 0.0734(11) 0.0100(8) -0.0230(7) -0.0002(7) O23 0.0287(6) 0.0681(8) 0.0859(9) 0.0174(7) 0.0096(5) 0.0022(5) C24 0.0421(11) 0.135(2) 0.175(2) 0.0075(19) 0.0345(14) 0.0050(13) O25 0.0706(8) 0.0394(7) 0.1040(10) 0.0117(6) -0.0539(7) -0.0079(6) C26 0.1015(17) 0.0396(10) 0.1122(17) 0.0027(10) -0.0509(13) -0.0082(10) _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 C9 1.3810(15) . ? O1 C2 1.4282(16) . ? C2 O3 1.4219(16) . ? O3 C4 1.3795(15) . ? C4 C5 1.3694(17) . ? C4 C9 1.3785(17) . ? C5 C6 1.4081(17) . ? C6 C7 1.3986(17) . ? C6 C10 1.4817(17) . ? C7 C8 1.3908(18) . ? C8 C9 1.3665(18) . ? C10 C18 1.3335(18) . ? C10 C11 1.5030(17) . ? C11 O12 1.4367(14) . ? C11 C15 1.5163(18) . ? O12 C13 1.4284(15) . ? C13 O14 1.4469(17) . ? C13 C19 1.507(2) . ? C13 C20 1.514(2) . ? O14 C15 1.4315(16) . ? C15 C16 1.5168(19) . ? C16 C17 1.5300(18) . ? C17 C18 1.5008(18) . ? C17 C21 1.5338(18) . ? C21 C22 1.498(2) . ? C22 O23 1.4097(19) . ? C22 O25 1.4154(19) . ? O23 C24 1.442(2) . ? O25 C26 1.417(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 C9 O1 C2 105.02(9) . . ? O3 C2 O1 108.43(10) . . ? C4 O3 C2 105.48(10) . . ? C5 C4 C9 122.51(12) . . ? C5 C4 O3 127.86(11) . . ? C9 C4 O3 109.62(11) . . ? C4 C5 C6 117.49(11) . . ? C7 C6 C5 118.91(11) . . ? C7 C6 C10 119.49(11) . . ? C5 C6 C10 121.59(11) . . ? C8 C7 C6 122.68(12) . . ? C9 C8 C7 116.77(11) . . ? C8 C9 C4 121.62(12) . . ? C8 C9 O1 128.43(11) . . ? C4 C9 O1 109.92(11) . . ? C18 C10 C6 122.00(11) . . ? C18 C10 C11 119.80(11) . . ? C6 C10 C11 118.18(11) . . ? O12 C11 C10 110.65(9) . . ? O12 C11 C15 102.08(10) . . ? C10 C11 C15 115.35(11) . . ? C13 O12 C11 106.79(9) . . ? O12 C13 O14 105.65(10) . . ? O12 C13 C19 111.19(12) . . ? O14 C13 C19 109.01(11) . . ? O12 C13 C20 107.61(11) . . ? O14 C13 C20 110.19(13) . . ? C19 C13 C20 112.94(13) . . ? C15 O14 C13 108.93(9) . . ? O14 C15 C11 102.67(10) . . ? O14 C15 C16 112.79(11) . . ? C11 C15 C16 112.14(11) . . ? C15 C16 C17 110.62(11) . . ? C18 C17 C16 109.57(11) . . ? C18 C17 C21 109.34(11) . . ? C16 C17 C21 112.16(11) . . ? C10 C18 C17 126.20(12) . . ? C22 C21 C17 114.14(12) . . ? O23 C22 O25 111.66(13) . . ? O23 C22 C21 106.93(11) . . ? O25 C22 C21 113.68(14) . . ? C22 O23 C24 113.87(16) . . ? C22 O25 C26 115.12(12) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.252 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.038 #===END data_16 _database_code_depnum_ccdc_archive 'CCDC 792817' #TrackingRef 'OBC 08-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O5, H2 O' _chemical_formula_sum 'C21 H29 N O6' _chemical_formula_weight 391.45 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)/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 7.2818(1) _cell_length_b 33.8728(3) _cell_length_c 8.3252(1) _cell_angle_alpha 90.00 _cell_angle_beta 104.148(1) _cell_angle_gamma 90.00 _cell_volume 1991.17(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16347 _cell_measurement_theta_min 2.6044 _cell_measurement_theta_max 71.1645 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75352 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET) (compiled Apr 27 2007,17:53:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 '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 25468 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 5.22 _diffrn_reflns_theta_max 71.29 _reflns_number_total 3808 _reflns_number_gt 3426 _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^)+(0.0673P)^2^+0.7003P] 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 3808 _refine_ls_number_parameters 263 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.087 _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 1.41313(16) 0.09730(3) 1.54419(14) 0.0420(3) Uani 1 1 d . . . C2 C 1.3420(3) 0.05756(5) 1.5425(2) 0.0469(4) Uani 1 1 d . . . H2A H 1.3923 0.0410 1.4651 0.056 Uiso 1 1 calc R . . H2B H 1.3813 0.0458 1.6546 0.056 Uiso 1 1 calc R . . O3 O 1.13935(17) 0.05968(3) 1.48998(16) 0.0465(3) Uani 1 1 d . . . C4 C 1.1013(2) 0.09581(4) 1.41372(18) 0.0340(3) Uani 1 1 d . . . C5 C 0.9337(2) 0.10909(4) 1.31584(18) 0.0327(3) Uani 1 1 d . . . H5A H 0.8236 0.0930 1.2926 0.039 Uiso 1 1 calc R . . C6 C 0.9306(2) 0.14778(4) 1.25042(17) 0.0284(3) Uani 1 1 d . . . C7 C 1.0962(2) 0.17050(4) 1.29090(18) 0.0311(3) Uani 1 1 d . . . H7A H 1.0930 0.1966 1.2487 0.037 Uiso 1 1 calc R . . C8 C 1.2657(2) 0.15627(5) 1.39084(18) 0.0337(3) Uani 1 1 d . . . H8A H 1.3767 0.1721 1.4175 0.040 Uiso 1 1 calc R . . C9 C 1.2652(2) 0.11843(5) 1.44885(18) 0.0332(3) Uani 1 1 d . . . C10 C 0.7578(2) 0.16274(4) 1.13138(17) 0.0283(3) Uani 1 1 d . . . C11 C 0.7841(2) 0.19718(4) 1.02460(18) 0.0289(3) Uani 1 1 d . . . H11A H 0.8448 0.2196 1.0965 0.035 Uiso 1 1 calc R . . O12 O 0.90202(13) 0.18561(3) 0.91645(12) 0.0298(2) Uani 1 1 d . . . C13 C 0.8673(2) 0.21328(4) 0.78293(18) 0.0320(3) Uani 1 1 d . . . O14 O 0.68022(15) 0.22895(3) 0.77235(13) 0.0353(3) Uani 1 1 d . . . C15 C 0.6069(2) 0.21175(4) 0.90120(18) 0.0316(3) Uani 1 1 d . . . H15A H 0.5422 0.2324 0.9536 0.038 Uiso 1 1 calc R . . C16 C 0.4720(2) 0.17834(5) 0.83645(19) 0.0339(3) Uani 1 1 d . . . H16A H 0.5333 0.1596 0.7744 0.041 Uiso 1 1 calc R . . H16B H 0.3577 0.1890 0.7587 0.041 Uiso 1 1 calc R . . C17 C 0.4135(2) 0.15633(4) 0.97597(19) 0.0330(3) Uani 1 1 d . . . H17A H 0.3259 0.1733 1.0216 0.040 Uiso 1 1 calc R . . C18 C 0.5856(2) 0.14654(4) 1.11228(18) 0.0319(3) Uani 1 1 d . . . H18A H 0.5710 0.1273 1.1912 0.038 Uiso 1 1 calc R . . C19 C 1.0071(2) 0.24698(5) 0.8201(2) 0.0396(4) Uani 1 1 d . . . H19A H 0.9973 0.2602 0.9225 0.059 Uiso 1 1 calc R . . H19B H 0.9790 0.2659 0.7284 0.059 Uiso 1 1 calc R . . H19C H 1.1358 0.2367 0.8335 0.059 Uiso 1 1 calc R . . C20 C 0.8705(2) 0.19122(5) 0.6259(2) 0.0392(4) Uani 1 1 d . . . H20A H 0.7763 0.1700 0.6084 0.059 Uiso 1 1 calc R . . H20B H 0.9966 0.1799 0.6357 0.059 Uiso 1 1 calc R . . H20C H 0.8405 0.2095 0.5317 0.059 Uiso 1 1 calc R . . C21 C 0.3087(2) 0.11871(5) 0.9012(2) 0.0367(4) Uani 1 1 d . . . H21A H 0.2115 0.1262 0.8002 0.044 Uiso 1 1 calc R . . H21B H 0.4004 0.1011 0.8664 0.044 Uiso 1 1 calc R . . C22 C 0.2130(2) 0.09560(5) 1.0128(2) 0.0387(4) Uani 1 1 d . . . H22A H 0.3043 0.0902 1.1199 0.046 Uiso 1 1 calc R . . H22B H 0.1063 0.1110 1.0349 0.046 Uiso 1 1 calc R . . N23 N 0.14246(19) 0.05805(4) 0.92978(18) 0.0392(3) Uani 1 1 d . . . O24 O 0.27860(19) 0.03201(4) 0.9344(2) 0.0587(4) Uani 1 1 d . . . C25 C -0.0310(2) 0.05122(5) 0.8522(2) 0.0430(4) Uani 1 1 d . . . C26 C -0.0778(3) 0.01234(6) 0.7680(3) 0.0571(5) Uani 1 1 d . . . H26A H -0.0647 0.0142 0.6538 0.086 Uiso 1 1 calc R . . H26B H -0.2084 0.0051 0.7671 0.086 Uiso 1 1 calc R . . H26C H 0.0088 -0.0079 0.8277 0.086 Uiso 1 1 calc R . . C27 C -0.1836(3) 0.08054(7) 0.8411(3) 0.0644(6) Uani 1 1 d . . . H27A H -0.2707 0.0715 0.9063 0.097 Uiso 1 1 calc R . . H27B H -0.2529 0.0837 0.7251 0.097 Uiso 1 1 calc R . . H27C H -0.1285 0.1059 0.8844 0.097 Uiso 1 1 calc R . . O30 O 0.5903(3) 0.03428(5) 1.2076(3) 0.0794(5) Uani 1 1 d D . . H30A H 0.486(3) 0.0341(12) 1.124(3) 0.145(15) Uiso 1 1 d D . . H30B H 0.658(4) 0.0128(6) 1.196(5) 0.121(13) Uiso 1 1 d 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 0.0378(6) 0.0408(6) 0.0402(6) 0.0021(5) -0.0047(5) 0.0015(5) C2 0.0473(10) 0.0381(9) 0.0472(10) 0.0019(7) -0.0040(8) 0.0037(7) O3 0.0458(7) 0.0348(6) 0.0513(7) 0.0092(5) -0.0026(5) -0.0025(5) C4 0.0398(8) 0.0305(7) 0.0299(7) 0.0018(6) 0.0049(6) -0.0022(6) C5 0.0323(8) 0.0324(7) 0.0317(7) 0.0001(6) 0.0048(6) -0.0047(6) C6 0.0304(7) 0.0314(7) 0.0237(6) -0.0016(5) 0.0072(5) -0.0019(6) C7 0.0336(8) 0.0310(7) 0.0281(7) -0.0002(5) 0.0065(6) -0.0032(6) C8 0.0321(8) 0.0367(8) 0.0299(7) -0.0020(6) 0.0031(6) -0.0062(6) C9 0.0324(8) 0.0383(8) 0.0258(7) -0.0017(6) 0.0011(6) 0.0001(6) C10 0.0304(7) 0.0290(7) 0.0260(7) -0.0029(5) 0.0076(5) 0.0005(5) C11 0.0283(7) 0.0292(7) 0.0296(7) -0.0020(5) 0.0077(6) 0.0014(5) O12 0.0282(5) 0.0322(5) 0.0303(5) 0.0047(4) 0.0096(4) 0.0056(4) C13 0.0307(7) 0.0336(7) 0.0322(7) 0.0065(6) 0.0085(6) 0.0065(6) O14 0.0323(5) 0.0378(6) 0.0369(6) 0.0088(4) 0.0106(4) 0.0094(4) C15 0.0310(7) 0.0327(7) 0.0323(7) 0.0013(6) 0.0100(6) 0.0064(6) C16 0.0271(7) 0.0401(8) 0.0330(7) -0.0007(6) 0.0045(6) 0.0037(6) C17 0.0257(7) 0.0356(8) 0.0378(8) -0.0030(6) 0.0079(6) 0.0008(6) C18 0.0306(7) 0.0343(7) 0.0314(7) -0.0010(6) 0.0089(6) -0.0011(6) C19 0.0401(9) 0.0369(8) 0.0430(9) 0.0062(7) 0.0129(7) -0.0004(7) C20 0.0396(9) 0.0454(9) 0.0332(8) 0.0025(6) 0.0099(6) 0.0085(7) C21 0.0295(7) 0.0409(8) 0.0385(8) -0.0042(6) 0.0058(6) -0.0014(6) C22 0.0345(8) 0.0384(8) 0.0430(9) -0.0066(7) 0.0092(7) -0.0031(6) N23 0.0348(7) 0.0349(7) 0.0468(8) -0.0012(6) 0.0079(6) 0.0018(5) O24 0.0442(7) 0.0463(7) 0.0793(10) -0.0108(7) 0.0034(7) 0.0124(6) C25 0.0371(9) 0.0421(9) 0.0480(9) -0.0016(7) 0.0073(7) -0.0049(7) C26 0.0572(12) 0.0460(10) 0.0647(12) -0.0098(9) 0.0086(9) -0.0156(9) C27 0.0348(9) 0.0605(12) 0.0881(16) -0.0163(11) -0.0036(10) 0.0059(9) O30 0.0632(10) 0.0685(11) 0.0943(13) -0.0206(9) -0.0042(9) 0.0154(8) _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 C9 1.3727(18) . ? O1 C2 1.441(2) . ? C2 O3 1.435(2) . ? O3 C4 1.3753(19) . ? C4 C5 1.367(2) . ? C4 C9 1.388(2) . ? C5 C6 1.417(2) . ? C6 C7 1.401(2) . ? C6 C10 1.487(2) . ? C7 C8 1.395(2) . ? C8 C9 1.370(2) . ? C10 C18 1.342(2) . ? C10 C11 1.507(2) . ? C11 O12 1.4422(17) . ? C11 C15 1.522(2) . ? O12 C13 1.4285(17) . ? C13 O14 1.4443(17) . ? C13 C19 1.510(2) . ? C13 C20 1.511(2) . ? O14 C15 1.4336(18) . ? C15 C16 1.509(2) . ? C16 C17 1.526(2) . ? C17 C18 1.508(2) . ? C17 C21 1.537(2) . ? C21 C22 1.509(2) . ? C22 N23 1.479(2) . ? N23 C25 1.291(2) . ? N23 O24 1.3205(18) . ? C25 C27 1.477(3) . ? C25 C26 1.492(3) . ? 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 C9 O1 C2 104.62(12) . . ? O3 C2 O1 107.24(13) . . ? C4 O3 C2 105.15(12) . . ? C5 C4 O3 128.14(14) . . ? C5 C4 C9 122.69(14) . . ? O3 C4 C9 109.17(13) . . ? C4 C5 C6 117.49(14) . . ? C7 C6 C5 118.90(13) . . ? C7 C6 C10 120.77(13) . . ? C5 C6 C10 120.18(13) . . ? C8 C7 C6 122.56(14) . . ? C9 C8 C7 117.08(14) . . ? C8 C9 O1 128.48(14) . . ? C8 C9 C4 121.23(14) . . ? O1 C9 C4 110.28(13) . . ? C18 C10 C6 123.59(13) . . ? C18 C10 C11 119.74(13) . . ? C6 C10 C11 116.64(12) . . ? O12 C11 C10 109.81(11) . . ? O12 C11 C15 101.69(11) . . ? C10 C11 C15 116.14(12) . . ? C13 O12 C11 106.76(10) . . ? O12 C13 O14 105.87(11) . . ? O12 C13 C19 110.74(12) . . ? O14 C13 C19 108.26(12) . . ? O12 C13 C20 108.15(12) . . ? O14 C13 C20 110.04(12) . . ? C19 C13 C20 113.50(13) . . ? C15 O14 C13 108.86(10) . . ? O14 C15 C16 111.49(12) . . ? O14 C15 C11 103.16(11) . . ? C16 C15 C11 111.61(12) . . ? C15 C16 C17 111.90(12) . . ? C18 C17 C16 110.18(12) . . ? C18 C17 C21 111.21(13) . . ? C16 C17 C21 107.47(13) . . ? C10 C18 C17 125.44(14) . . ? C22 C21 C17 116.03(13) . . ? N23 C22 C21 108.56(13) . . ? C25 N23 O24 122.04(15) . . ? C25 N23 C22 125.01(14) . . ? O24 N23 C22 112.85(13) . . ? N23 C25 C27 122.70(16) . . ? N23 C25 C26 118.46(17) . . ? C27 C25 C26 118.83(17) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 71.29 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.352 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.042 #===END data_20 _database_code_depnum_ccdc_archive 'CCDC 792818' #TrackingRef 'OBC 08-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N O4' _chemical_formula_sum 'C19 H23 N O4' _chemical_formula_weight 329.38 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 Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 10.695(1) _cell_length_b 10.695(1) _cell_length_c 25.134(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2489.7(5) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 8 _cell_measurement_theta_max 11.5 _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.092 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method '\w-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2331 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 23.03 _reflns_number_total 2331 _reflns_number_gt 1415 _reflns_threshold_expression >2sigma(I) _computing_data_collection Stoe_Stadi-4 _computing_cell_refinement 'xtal latcon' _computing_data_reduction 'xtal REFCAL LSABS SORTRF' _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+ 0.0446 _refine_ls_wR_factor_obs+ 0.0727 _refine_ls_abs_structure_Flack+ 0.0(17) _refine_ls_R_factor_obs- 0.0446 _refine_ls_wR_factor_obs- 0.0728 _refine_ls_abs_structure_Flack- 2.6(17) ; _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^)+(0.0330P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0072(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1134 Friedel pairs' _refine_ls_abs_structure_Flack -1.6(17) _refine_ls_number_reflns 2331 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 0.7111(3) 1.2506(3) 0.55627(12) 0.0633(9) Uani 1 1 d . . . C2 C 0.5906(5) 1.1982(4) 0.59111(18) 0.0632(13) Uani 1 1 d . . . H2A H 0.5251 1.2303 0.5790 0.076 Uiso 1 1 calc R . . H2B H 0.6229 1.2355 0.6267 0.076 Uiso 1 1 calc R . . O3 O 0.5182(3) 1.0442(3) 0.59172(14) 0.0646(9) Uani 1 1 d . . . C4 C 0.5854(4) 1.0074(4) 0.55349(16) 0.0415(10) Uani 1 1 d . . . C5 C 0.5510(4) 0.8732(4) 0.53641(16) 0.0400(10) Uani 1 1 d . . . H5A H 0.4713 0.7914 0.5501 0.048 Uiso 1 1 calc R . . C6 C 0.6393(4) 0.8612(4) 0.49754(14) 0.0350(10) Uani 1 1 d . . . C7 C 0.6079(4) 0.7135(4) 0.47856(14) 0.0379(10) Uani 1 1 d . . . H7A H 0.5421 0.6859 0.4481 0.046 Uiso 1 1 calc R . . C8 C 0.5429(4) 0.5916(4) 0.51884(16) 0.0370(10) Uani 1 1 d . . . H8A H 0.5913 0.6250 0.5533 0.044 Uiso 1 1 calc R . . O9 O 0.3908(3) 0.5372(2) 0.52452(11) 0.0427(7) Uani 1 1 d . . . C10 C 0.3282(4) 0.3879(4) 0.53846(16) 0.0447(11) Uani 1 1 d . . . O11 O 0.4082(3) 0.3385(3) 0.50993(12) 0.0593(8) Uani 1 1 d . . . C12 C 0.5494(4) 0.4572(4) 0.50028(17) 0.0439(11) Uani 1 1 d . . . H12A H 0.6185 0.4465 0.5227 0.053 Uiso 1 1 calc R . . C13 C 0.5922(4) 0.4629(4) 0.44288(17) 0.0515(11) Uani 1 1 d . . . H13A H 0.5235 0.4711 0.4200 0.062 Uiso 1 1 calc R . . H13B H 0.5928 0.3753 0.4335 0.062 Uiso 1 1 calc R . . C14 C 0.7420(4) 0.5933(4) 0.43536(16) 0.0473(11) Uani 1 1 d . . . H14A H 0.8108 0.5749 0.4547 0.057 Uiso 1 1 calc R . . C15 C 0.7986(5) 0.6385(4) 0.37887(18) 0.0556(12) Uani 1 1 d . . . H15A H 0.8545 0.5945 0.3676 0.067 Uiso 1 1 calc R . . H15B H 0.7203 0.6129 0.3539 0.067 Uiso 1 1 calc R . . C16 C 0.8931(4) 0.8014(4) 0.38395(17) 0.0529(11) Uani 1 1 d . . . H16A H 0.9836 0.8280 0.4017 0.063 Uiso 1 1 calc R . . H16B H 0.9128 0.8485 0.3495 0.063 Uiso 1 1 calc R . . N17 N 0.8017(3) 0.8352(3) 0.41625(11) 0.0414(8) Uani 1 1 d . . . C18 C 0.8613(4) 0.9797(4) 0.43782(15) 0.0436(11) Uani 1 1 d . . . H18A H 0.8796 1.0474 0.4091 0.052 Uiso 1 1 calc R . . H18B H 0.9524 1.0075 0.4553 0.052 Uiso 1 1 calc R . . C19 C 0.7579(4) 0.9853(4) 0.47719(15) 0.0370(10) Uani 1 1 d . . . C20 C 0.7882(4) 1.1220(4) 0.49521(15) 0.0454(11) Uani 1 1 d . . . H20A H 0.8667 1.2055 0.4819 0.054 Uiso 1 1 calc R . . C21 C 0.6996(4) 1.1295(4) 0.53281(16) 0.0429(10) Uani 1 1 d . . . C22 C 0.7495(4) 0.7292(4) 0.45918(14) 0.0381(10) Uani 1 1 d . . . H22A H 0.8196 0.7650 0.4884 0.046 Uiso 1 1 calc R . . C23 C 0.3376(5) 0.3692(5) 0.59713(17) 0.0628(13) Uani 1 1 d . . . H23A H 0.4369 0.4210 0.6081 0.094 Uiso 1 1 calc R . . H23B H 0.2973 0.2685 0.6051 0.094 Uiso 1 1 calc R . . H23C H 0.2846 0.4062 0.6158 0.094 Uiso 1 1 calc R . . C24 C 0.1758(4) 0.3110(4) 0.5193(2) 0.0696(14) Uani 1 1 d . . . H24A H 0.1740 0.3247 0.4816 0.104 Uiso 1 1 calc R . . H24B H 0.1224 0.3489 0.5371 0.104 Uiso 1 1 calc R . . H24C H 0.1328 0.2098 0.5269 0.104 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 0.074(2) 0.0375(17) 0.073(2) -0.0056(17) 0.0163(18) 0.0246(16) C2 0.082(3) 0.042(3) 0.069(3) -0.002(2) 0.016(3) 0.035(3) O3 0.073(2) 0.0421(18) 0.076(2) 0.0000(18) 0.0269(18) 0.0268(17) C4 0.047(3) 0.032(3) 0.048(3) -0.003(2) 0.003(2) 0.022(2) C5 0.035(2) 0.033(2) 0.047(3) 0.0063(19) -0.0032(19) 0.014(2) C6 0.031(2) 0.033(2) 0.039(3) -0.0038(18) -0.0065(19) 0.014(2) C7 0.037(2) 0.036(2) 0.040(3) -0.0029(19) -0.0024(19) 0.0174(19) C8 0.027(2) 0.036(2) 0.044(3) 0.001(2) -0.0007(19) 0.0126(18) O9 0.0389(16) 0.0298(15) 0.0551(17) 0.0043(14) 0.0029(14) 0.0138(13) C10 0.043(3) 0.039(2) 0.051(3) 0.005(2) 0.009(2) 0.020(2) O11 0.0572(19) 0.0357(16) 0.076(2) 0.0022(15) 0.0242(16) 0.0165(16) C12 0.044(3) 0.037(2) 0.051(3) 0.006(2) 0.008(2) 0.021(2) C13 0.057(3) 0.044(3) 0.058(3) -0.003(2) 0.011(2) 0.029(2) C14 0.051(3) 0.047(3) 0.048(3) 0.004(2) 0.004(2) 0.028(2) C15 0.067(3) 0.051(3) 0.053(3) -0.001(2) 0.014(3) 0.033(2) C16 0.060(3) 0.060(3) 0.043(3) 0.010(2) 0.017(2) 0.033(2) N17 0.048(2) 0.040(2) 0.038(2) 0.0021(17) 0.0093(17) 0.0227(17) C18 0.039(2) 0.044(3) 0.044(3) 0.005(2) 0.003(2) 0.018(2) C19 0.031(2) 0.036(3) 0.041(3) 0.003(2) -0.007(2) 0.0148(19) C20 0.042(3) 0.035(3) 0.050(3) 0.005(2) -0.005(2) 0.012(2) C21 0.050(3) 0.030(2) 0.047(3) -0.004(2) -0.003(2) 0.019(2) C22 0.040(2) 0.037(2) 0.038(3) 0.0027(19) -0.0025(18) 0.019(2) C23 0.069(3) 0.055(3) 0.061(3) 0.012(3) 0.011(3) 0.029(3) C24 0.051(3) 0.050(3) 0.092(4) 0.000(3) -0.006(3) 0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C21 1.371(4) . ? O1 C2 1.421(5) . ? C2 O3 1.427(4) . ? O3 C4 1.370(4) . ? C4 C5 1.361(5) . ? C4 C21 1.368(5) . ? C5 C6 1.408(5) . ? C6 C19 1.396(5) . ? C6 C7 1.519(5) . ? C7 C8 1.517(5) . ? C7 C22 1.518(5) . ? C8 O9 1.436(4) . ? C8 C12 1.544(5) . ? O9 C10 1.433(4) . ? C10 O11 1.406(4) . ? C10 C24 1.491(6) . ? C10 C23 1.498(5) . ? O11 C12 1.426(4) . ? C12 C13 1.506(5) . ? C13 C14 1.521(5) . ? C14 C15 1.524(5) . ? C14 C22 1.537(5) . ? C15 C16 1.521(5) . ? C16 N17 1.449(4) . ? N17 C18 1.450(5) . ? N17 C22 1.459(4) . ? C18 C19 1.508(5) . ? C19 C20 1.404(5) . ? C20 C21 1.369(5) . ? 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 C21 O1 C2 104.9(3) . . ? O1 C2 O3 108.9(3) . . ? C4 O3 C2 105.3(3) . . ? C5 C4 C21 121.9(4) . . ? C5 C4 O3 128.3(4) . . ? C21 C4 O3 109.8(3) . . ? C4 C5 C6 118.4(4) . . ? C19 C6 C5 120.0(3) . . ? C19 C6 C7 119.8(3) . . ? C5 C6 C7 120.2(3) . . ? C8 C7 C22 108.2(3) . . ? C8 C7 C6 116.9(3) . . ? C22 C7 C6 107.2(3) . . ? O9 C8 C7 110.7(3) . . ? O9 C8 C12 102.9(3) . . ? C7 C8 C12 112.6(3) . . ? C10 O9 C8 106.2(3) . . ? O11 C10 O9 105.2(3) . . ? O11 C10 C24 109.3(4) . . ? O9 C10 C24 108.0(3) . . ? O11 C10 C23 111.0(3) . . ? O9 C10 C23 111.4(3) . . ? C24 C10 C23 111.8(4) . . ? C10 O11 C12 108.9(3) . . ? O11 C12 C13 111.4(3) . . ? O11 C12 C8 104.9(3) . . ? C13 C12 C8 113.9(3) . . ? C12 C13 C14 108.4(3) . . ? C13 C14 C15 118.4(4) . . ? C13 C14 C22 110.6(3) . . ? C15 C14 C22 103.8(3) . . ? C16 C15 C14 102.5(3) . . ? N17 C16 C15 100.9(3) . . ? C16 N17 C18 118.9(3) . . ? C16 N17 C22 105.3(3) . . ? C18 N17 C22 110.2(3) . . ? N17 C18 C19 110.3(3) . . ? C6 C19 C20 119.9(4) . . ? C6 C19 C18 122.6(3) . . ? C20 C19 C18 117.5(4) . . ? C21 C20 C19 118.5(4) . . ? C4 C21 C20 121.3(4) . . ? C4 C21 O1 110.7(4) . . ? C20 C21 O1 127.9(4) . . ? N17 C22 C7 107.2(3) . . ? N17 C22 C14 105.4(3) . . ? C7 C22 C14 116.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.128 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.034 #===END data_28 _database_code_depnum_ccdc_archive 'CCDC 792819' #TrackingRef 'OBC 08-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H26 Cl N O5' _chemical_formula_sum 'C25 H26 Cl N O5' _chemical_formula_weight 455.92 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' Cl Cl 0.3639 0.7018 '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 6.0988(2) _cell_length_b 11.8551(4) _cell_length_c 16.3205(5) _cell_angle_alpha 102.804(3) _cell_angle_beta 98.740(3) _cell_angle_gamma 102.130(3) _cell_volume 1100.31(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7226 _cell_measurement_theta_min 2.8355 _cell_measurement_theta_max 71.2573 _exptl_crystal_description plates _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75238 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET) (compiled Apr 27 2007,17:53:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54248 _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 16799 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 71.53 _reflns_number_total 4218 _reflns_number_gt 3060 _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^)+(0.0696P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4218 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 N1 N 0.6775(2) 0.74922(11) 0.62301(8) 0.0489(3) Uani 1 1 d . . . C2 C 0.4999(2) 0.79823(12) 0.66015(9) 0.0443(3) Uani 1 1 d . . . H2A H 0.3540 0.7370 0.6437 0.053 Uiso 1 1 calc R . . C3 C 0.5715(3) 0.84321(12) 0.75940(9) 0.0440(3) Uani 1 1 d . . . H3A H 0.7290 0.8932 0.7736 0.053 Uiso 1 1 calc R . . C4 C 0.4197(3) 0.92203(13) 0.79310(9) 0.0496(4) Uani 1 1 d . . . H4A H 0.2645 0.8728 0.7871 0.060 Uiso 1 1 calc R . . O5 O 0.5154(2) 0.98062(10) 0.88134(7) 0.0661(3) Uani 1 1 d . . . C6 C 0.4775(3) 1.09754(14) 0.89679(10) 0.0568(4) Uani 1 1 d . . . O7 O 0.4979(2) 1.13045(9) 0.81909(7) 0.0603(3) Uani 1 1 d . . . C8 C 0.4090(3) 1.02458(12) 0.75032(10) 0.0504(4) Uani 1 1 d . . . H8A H 0.2491 1.0192 0.7257 0.061 Uiso 1 1 calc R . . C9 C 0.5481(3) 1.02489(13) 0.68173(10) 0.0551(4) Uani 1 1 d . . . H9A H 0.7099 1.0444 0.7078 0.066 Uiso 1 1 calc R . . H9B H 0.5226 1.0853 0.6525 0.066 Uiso 1 1 calc R . . C10 C 0.4797(3) 0.90169(13) 0.61654(9) 0.0509(4) Uani 1 1 d . . . H10A H 0.3214 0.8868 0.5854 0.061 Uiso 1 1 calc R . . C11 C 0.6372(3) 0.89388(15) 0.55215(10) 0.0587(4) Uani 1 1 d . . . H11A H 0.5539 0.8434 0.4961 0.070 Uiso 1 1 calc R . . H11B H 0.7064 0.9725 0.5464 0.070 Uiso 1 1 calc R . . C12 C 0.8161(3) 0.83948(14) 0.59109(10) 0.0573(4) Uani 1 1 d . . . H12A H 0.8929 0.8035 0.5483 0.069 Uiso 1 1 calc R . . H12B H 0.9293 0.8984 0.6374 0.069 Uiso 1 1 calc R . . C13 C 0.7430(3) 0.64718(13) 0.62620(9) 0.0481(4) Uani 1 1 d . . . O13 O 0.9369(2) 0.63992(11) 0.61832(8) 0.0647(3) Uani 1 1 d . . . C14 C 0.5719(3) 0.54039(12) 0.63214(9) 0.0467(3) Uani 1 1 d . . . C15 C 0.3448(3) 0.51077(13) 0.58964(9) 0.0490(4) Uani 1 1 d . . . H15A H 0.2936 0.5604 0.5584 0.059 Uiso 1 1 calc R . . C16 C 0.1933(3) 0.40800(14) 0.59324(10) 0.0551(4) Uani 1 1 d . . . H16A H 0.0407 0.3884 0.5649 0.066 Uiso 1 1 calc R . . C17 C 0.2722(3) 0.33551(14) 0.63926(10) 0.0575(4) Uani 1 1 d . . . Cl Cl 0.07925(10) 0.20707(4) 0.64440(4) 0.0869(2) Uani 1 1 d . . . C18 C 0.4986(3) 0.36074(14) 0.68048(10) 0.0604(4) Uani 1 1 d . . . H18A H 0.5494 0.3098 0.7105 0.072 Uiso 1 1 calc R . . C19 C 0.6480(3) 0.46329(14) 0.67621(10) 0.0537(4) Uani 1 1 d . . . H19A H 0.8016 0.4811 0.7031 0.064 Uiso 1 1 calc R . . C20 C 0.5697(3) 0.74251(12) 0.80238(8) 0.0462(3) Uani 1 1 d . . . C21 C 0.3605(3) 0.65947(13) 0.79514(9) 0.0502(4) Uani 1 1 d . . . H21A H 0.2231 0.6662 0.7654 0.060 Uiso 1 1 calc R . . C22 C 0.3682(3) 0.56878(13) 0.83362(10) 0.0581(4) Uani 1 1 d . . . O23 O 0.1899(3) 0.47615(12) 0.83291(9) 0.0839(4) Uani 1 1 d . . . C24 C 0.2926(6) 0.4046(2) 0.87973(14) 0.1003(8) Uani 1 1 d . . . H24A H 0.2267 0.4012 0.9299 0.120 Uiso 1 1 calc R . . H24B H 0.2620 0.3237 0.8438 0.120 Uiso 1 1 calc R . . O25 O 0.5333(3) 0.45505(13) 0.90566(9) 0.0915(5) Uani 1 1 d . . . C26 C 0.5709(4) 0.55670(15) 0.87719(10) 0.0645(5) Uani 1 1 d . . . C27 C 0.7759(4) 0.63628(16) 0.88608(10) 0.0673(5) Uani 1 1 d . . . H27A H 0.9120 0.6284 0.9159 0.081 Uiso 1 1 calc R . . C28 C 0.7700(3) 0.73045(14) 0.84774(9) 0.0560(4) Uani 1 1 d . . . H28A H 0.9061 0.7870 0.8530 0.067 Uiso 1 1 calc R . . C29 C 0.2436(4) 1.09439(18) 0.91663(14) 0.0775(6) Uani 1 1 d . . . H29A H 0.1290 1.0399 0.8696 0.116 Uiso 1 1 calc R . . H29B H 0.2179 1.1729 0.9250 0.116 Uiso 1 1 calc R . . H29C H 0.2345 1.0683 0.9680 0.116 Uiso 1 1 calc R . . C30 C 0.6654(4) 1.18121(18) 0.96805(12) 0.0800(6) Uani 1 1 d . . . H30A H 0.8112 1.1799 0.9531 0.120 Uiso 1 1 calc R . . H30B H 0.6598 1.1564 1.0200 0.120 Uiso 1 1 calc R . . H30C H 0.6453 1.2609 0.9766 0.120 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 N1 0.0481(7) 0.0456(7) 0.0513(7) 0.0080(5) 0.0138(5) 0.0106(5) C2 0.0433(8) 0.0386(7) 0.0469(7) 0.0056(6) 0.0079(6) 0.0085(6) C3 0.0448(8) 0.0376(7) 0.0464(8) 0.0068(6) 0.0073(6) 0.0095(6) C4 0.0570(9) 0.0413(8) 0.0508(8) 0.0091(6) 0.0138(7) 0.0144(7) O5 0.1051(10) 0.0529(7) 0.0470(6) 0.0082(5) 0.0153(6) 0.0401(7) C6 0.0740(11) 0.0441(8) 0.0544(9) 0.0077(6) 0.0156(8) 0.0234(8) O7 0.0820(8) 0.0387(5) 0.0551(6) 0.0054(4) 0.0138(6) 0.0117(5) C8 0.0572(9) 0.0381(7) 0.0523(8) 0.0069(6) 0.0056(7) 0.0134(6) C9 0.0698(11) 0.0408(8) 0.0548(9) 0.0141(6) 0.0111(8) 0.0141(7) C10 0.0544(9) 0.0470(8) 0.0477(8) 0.0099(6) 0.0056(7) 0.0114(7) C11 0.0705(11) 0.0536(9) 0.0505(9) 0.0140(7) 0.0145(8) 0.0109(8) C12 0.0546(10) 0.0548(9) 0.0563(9) 0.0080(7) 0.0161(7) 0.0038(7) C13 0.0464(9) 0.0514(8) 0.0423(7) 0.0043(6) 0.0052(6) 0.0147(7) O13 0.0461(7) 0.0739(8) 0.0760(8) 0.0174(6) 0.0116(5) 0.0223(6) C14 0.0488(8) 0.0438(7) 0.0445(7) 0.0009(6) 0.0093(6) 0.0169(6) C15 0.0526(9) 0.0435(8) 0.0469(8) 0.0037(6) 0.0056(6) 0.0154(7) C16 0.0546(10) 0.0466(8) 0.0566(9) 0.0035(7) 0.0059(7) 0.0118(7) C17 0.0703(11) 0.0407(8) 0.0571(9) 0.0053(7) 0.0155(8) 0.0108(7) Cl 0.0967(4) 0.0577(3) 0.1004(4) 0.0269(2) 0.0182(3) 0.0017(3) C18 0.0760(12) 0.0486(9) 0.0574(9) 0.0098(7) 0.0104(8) 0.0247(8) C19 0.0567(10) 0.0514(9) 0.0511(8) 0.0047(7) 0.0059(7) 0.0227(7) C20 0.0560(9) 0.0402(7) 0.0407(7) 0.0037(6) 0.0089(6) 0.0167(6) C21 0.0592(9) 0.0432(8) 0.0502(8) 0.0116(6) 0.0130(7) 0.0168(7) C22 0.0801(12) 0.0412(8) 0.0530(9) 0.0097(7) 0.0193(8) 0.0145(8) O23 0.1045(11) 0.0572(7) 0.0983(10) 0.0356(7) 0.0332(8) 0.0138(7) C24 0.171(3) 0.0569(12) 0.0770(14) 0.0304(10) 0.0270(16) 0.0225(15) O25 0.1434(16) 0.0612(8) 0.0791(9) 0.0332(7) 0.0160(9) 0.0352(9) C26 0.1051(16) 0.0485(9) 0.0463(8) 0.0136(7) 0.0135(9) 0.0337(10) C27 0.0859(14) 0.0632(11) 0.0516(9) 0.0096(8) -0.0019(9) 0.0338(10) C28 0.0616(10) 0.0512(9) 0.0496(8) 0.0045(7) 0.0039(7) 0.0168(7) C29 0.0900(15) 0.0610(11) 0.0884(13) 0.0137(9) 0.0356(11) 0.0281(10) C30 0.0902(15) 0.0741(12) 0.0617(11) -0.0071(9) 0.0056(10) 0.0244(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C13 1.3605(19) . ? N1 C12 1.460(2) . ? N1 C2 1.4784(18) . ? C2 C3 1.5502(19) . ? C2 C10 1.565(2) . ? C3 C20 1.512(2) . ? C3 C4 1.5242(19) . ? C4 O5 1.4241(18) . ? C4 C8 1.538(2) . ? O5 C6 1.4268(18) . ? C6 O7 1.4222(19) . ? C6 C30 1.502(2) . ? C6 C29 1.505(3) . ? O7 C8 1.4261(17) . ? C8 C9 1.504(2) . ? C9 C10 1.5360(19) . ? C10 C11 1.529(2) . ? C11 C12 1.509(2) . ? C13 O13 1.2271(18) . ? C13 C14 1.494(2) . ? C14 C15 1.385(2) . ? C14 C19 1.392(2) . ? C15 C16 1.384(2) . ? C16 C17 1.373(2) . ? C17 C18 1.380(3) . ? C17 Cl 1.7446(17) . ? C18 C19 1.380(2) . ? C20 C28 1.380(2) . ? C20 C21 1.409(2) . ? C21 C22 1.365(2) . ? C22 O23 1.370(2) . ? C22 C26 1.381(3) . ? O23 C24 1.436(3) . ? C24 O25 1.422(3) . ? O25 C26 1.373(2) . ? C26 C27 1.365(3) . ? C27 C28 1.400(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 C13 N1 C12 119.75(13) . . ? C13 N1 C2 130.30(12) . . ? C12 N1 C2 109.19(12) . . ? N1 C2 C3 111.32(12) . . ? N1 C2 C10 103.24(11) . . ? C3 C2 C10 112.54(11) . . ? C20 C3 C4 111.66(12) . . ? C20 C3 C2 112.79(11) . . ? C4 C3 C2 109.64(12) . . ? O5 C4 C3 108.59(12) . . ? O5 C4 C8 104.36(11) . . ? C3 C4 C8 114.32(12) . . ? C4 O5 C6 107.23(12) . . ? O7 C6 O5 104.07(11) . . ? O7 C6 C30 108.80(15) . . ? O5 C6 C30 109.12(15) . . ? O7 C6 C29 112.06(15) . . ? O5 C6 C29 110.22(15) . . ? C30 C6 C29 112.22(15) . . ? C6 O7 C8 107.35(11) . . ? O7 C8 C9 110.71(13) . . ? O7 C8 C4 104.42(12) . . ? C9 C8 C4 112.77(12) . . ? C8 C9 C10 110.19(13) . . ? C11 C10 C9 111.64(13) . . ? C11 C10 C2 105.05(12) . . ? C9 C10 C2 112.48(12) . . ? C12 C11 C10 103.43(13) . . ? N1 C12 C11 101.78(13) . . ? O13 C13 N1 120.32(15) . . ? O13 C13 C14 119.90(14) . . ? N1 C13 C14 119.59(13) . . ? C15 C14 C19 119.08(15) . . ? C15 C14 C13 122.14(14) . . ? C19 C14 C13 118.58(14) . . ? C16 C15 C14 120.60(15) . . ? C17 C16 C15 118.90(16) . . ? C16 C17 C18 121.99(16) . . ? C16 C17 Cl 118.56(14) . . ? C18 C17 Cl 119.45(14) . . ? C17 C18 C19 118.55(16) . . ? C18 C19 C14 120.83(16) . . ? C28 C20 C21 119.83(15) . . ? C28 C20 C3 120.92(14) . . ? C21 C20 C3 119.25(14) . . ? C22 C21 C20 117.13(16) . . ? C21 C22 O23 127.60(18) . . ? C21 C22 C26 122.23(17) . . ? O23 C22 C26 110.11(15) . . ? C22 O23 C24 104.85(18) . . ? O25 C24 O23 109.60(17) . . ? C26 O25 C24 104.79(17) . . ? C27 C26 O25 127.31(19) . . ? C27 C26 C22 122.04(16) . . ? O25 C26 C22 110.62(18) . . ? C26 C27 C28 116.28(17) . . ? C20 C28 C27 122.47(17) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 71.53 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.189 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.033 #===END