# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'S. Ley' 'Darren J. Dixon' 'Richard Guy' 'Felix Rodriguez' 'Tom D. Sheppard' _publ_contact_author_name 'Steven Ley' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SVL1000@CAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives ; data_sl0016 _database_code_depnum_ccdc_archive 'CCDC 171362' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H26 O8' _chemical_formula_weight 394.41 _chemical_melting_point ? _chemical_compound_source ? 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 9.8194(2) _cell_length_b 20.3687(9) _cell_length_c 10.7783(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.445(2) _cell_angle_gamma 90.00 _cell_volume 1930.18(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9968 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multiscan _exptl_absorpt_process_details 'Sortav Blessing (1995) ' _exptl_absorpt_correction_T_min 1.105 _exptl_absorpt_correction_T_max 0.937 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15205 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4394 _reflns_number_observed 3380 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 8 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.6495P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4386 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_obs 0.0472 _refine_ls_wR_factor_all 0.1615 _refine_ls_wR_factor_obs 0.1114 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_restrained_S_all 1.385 _refine_ls_restrained_S_obs 1.098 _refine_ls_shift/esd_max 0.005 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.18294(14) -0.00588(6) 0.52423(12) 0.0400(3) Uani 1 d . . O2 O 0.26119(13) -0.03580(5) 0.37146(11) 0.0317(3) Uani 1 d . . O3 O 0.17155(11) 0.08507(5) 0.23461(10) 0.0254(2) Uani 1 d . . O4 O 0.43290(12) 0.06908(6) 0.36059(11) 0.0319(3) Uani 1 d . . O5 O 0.15168(12) -0.03890(6) 0.13161(11) 0.0326(3) Uani 1 d . . O6 O -0.23642(15) 0.22294(7) 0.07945(14) 0.0504(4) Uani 1 d . . O7 O -0.31294(13) 0.12460(6) 0.09853(12) 0.0388(3) Uani 1 d . . O8 O -0.18577(15) 0.18955(7) 0.4010(2) 0.0497(4) Uani 1 d . . H8 H -0.1894(25) 0.2194(11) 0.4647(24) 0.060 Uiso 1 d . . C1 C 0.1981(2) 0.00832(8) 0.42290(15) 0.0275(3) Uani 1 d . . C2 C 0.1526(2) 0.07572(7) 0.35708(14) 0.0242(3) Uani 1 d . . H2 H 0.2165(2) 0.10907(7) 0.42678(14) 0.029 Uiso 1 calc R . C3 C 0.3022(2) 0.05301(8) 0.23878(15) 0.0262(3) Uani 1 d . . C4 C 0.2838(2) -0.02138(8) 0.24957(15) 0.0284(3) Uani 1 d . . C5 C 0.3094(2) 0.07274(9) 0.1063(2) 0.0334(4) Uani 1 d . . H5A H 0.3082(13) 0.12073(9) 0.0992(6) 0.050 Uiso 1 calc R . H5B H 0.2214(7) 0.0546(5) 0.0265(2) 0.050 Uiso 1 calc R . H5C H 0.4032(7) 0.0557(5) 0.1073(6) 0.050 Uiso 1 calc R . C6 C 0.4229(2) -0.06056(9) 0.2686(2) 0.0393(4) Uani 1 d . . H6A H 0.4121(7) -0.1059(2) 0.2933(13) 0.059 Uiso 1 calc R . H6B H 0.5137(2) -0.0409(4) 0.3428(9) 0.059 Uiso 1 calc R . H6C H 0.4328(8) -0.0602(5) 0.1821(4) 0.059 Uiso 1 calc R . C7 C 0.4798(2) 0.13636(9) 0.3746(2) 0.0400(4) Uani 1 d . . H7A H 0.5596(10) 0.1440(2) 0.4688(4) 0.060 Uiso 1 calc R . H7B H 0.3926(4) 0.16481(9) 0.3570(13) 0.060 Uiso 1 calc R . H7C H 0.5193(13) 0.1463(2) 0.3077(9) 0.060 Uiso 1 calc R . C8 C 0.1106(2) -0.10682(9) 0.1196(2) 0.0422(4) Uani 1 d . . H8B H 0.0166(8) -0.11372(14) 0.0344(7) 0.063 Uiso 1 calc R . H8C H 0.0948(14) -0.1200(2) 0.1997(7) 0.063 Uiso 1 calc R . H8D H 0.1924(7) -0.13330(10) 0.1165(13) 0.063 Uiso 1 calc R . C9 C -0.0143(2) 0.08975(7) 0.32079(15) 0.0253(3) Uani 1 d . . H9 H -0.0264(2) 0.08480(7) 0.40763(15) 0.030 Uiso 1 calc R . C10 C -0.0557(2) 0.16151(8) 0.2703(2) 0.0292(3) Uani 1 d . . H10 H 0.0252(2) 0.17783(8) 0.2457(2) 0.035 Uiso 1 calc R . C11 C -0.2074(2) 0.17159(9) 0.1433(2) 0.0349(4) Uani 1 d . . C12 C -0.1211(2) 0.04087(8) 0.2155(2) 0.0288(3) Uani 1 d . . H12A H -0.1005(2) 0.03915(8) 0.1336(2) 0.035 Uiso 1 calc R . H12B H -0.1048(2) -0.00354(8) 0.2570(2) 0.035 Uiso 1 calc R . C13 C -0.2821(2) 0.06237(9) 0.1726(2) 0.0346(4) Uani 1 d . . H13A H -0.3529(2) 0.02846(9) 0.1123(2) 0.042 Uiso 1 calc R . H13B H -0.2995(2) 0.06717(9) 0.2559(2) 0.042 Uiso 1 calc R . C14 C -0.0565(2) 0.20784(9) 0.3837(2) 0.0368(4) Uani 1 d . . H14 H -0.0702(2) 0.25398(9) 0.3485(2) 0.044 Uiso 1 calc R . C15 C 0.0904(2) 0.20375(8) 0.5163(2) 0.0384(4) Uani 1 d . . C16 C 0.1024(3) 0.16650(10) 0.6283(2) 0.0505(5) Uani 1 d . . H16 H 0.0155(3) 0.14468(10) 0.6253(2) 0.061 Uiso 1 calc R . C17 C 0.2410(3) 0.16108(12) 0.7446(2) 0.0650(7) Uani 1 d . . H17 H 0.2488(3) 0.13526(12) 0.8209(2) 0.078 Uiso 1 calc R . C18 C 0.3671(3) 0.19260(12) 0.7507(2) 0.0675(7) Uani 1 d . . H18 H 0.4614(3) 0.18906(12) 0.8315(2) 0.081 Uiso 1 calc R . C19 C 0.3572(3) 0.22964(11) 0.6392(3) 0.0628(6) Uani 1 d . . H19 H 0.4447(3) 0.25109(11) 0.6427(3) 0.075 Uiso 1 calc R . C20 C 0.2188(2) 0.23522(9) 0.5224(2) 0.0473(5) Uani 1 d . . H20 H 0.2116(2) 0.26075(9) 0.4459(2) 0.057 Uiso 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 0.0494(7) 0.0457(8) 0.0313(6) 0.0141(5) 0.0237(5) 0.0060(6) O2 0.0431(6) 0.0268(6) 0.0272(6) 0.0058(4) 0.0175(5) 0.0066(5) O3 0.0288(5) 0.0284(6) 0.0236(5) 0.0060(4) 0.0159(4) 0.0056(4) O4 0.0285(5) 0.0328(6) 0.0297(6) 0.0021(5) 0.0088(4) -0.0012(5) O5 0.0342(6) 0.0317(6) 0.0281(6) -0.0007(5) 0.0103(5) 0.0004(5) O6 0.0545(8) 0.0518(9) 0.0503(8) 0.0265(7) 0.0281(6) 0.0150(6) O7 0.0347(6) 0.0465(8) 0.0325(6) 0.0086(5) 0.0124(5) 0.0054(5) O8 0.0536(8) 0.0510(9) 0.0610(9) -0.0193(7) 0.0403(7) -0.0090(6) C1 0.0284(8) 0.0300(8) 0.0231(7) 0.0021(6) 0.0105(6) -0.0017(6) C2 0.0294(7) 0.0258(8) 0.0200(7) 0.0014(6) 0.0133(6) -0.0004(6) C3 0.0251(7) 0.0307(8) 0.0246(7) 0.0026(6) 0.0126(6) 0.0032(6) C4 0.0302(8) 0.0322(9) 0.0230(7) 0.0025(6) 0.0121(6) 0.0050(6) C5 0.0339(8) 0.0420(10) 0.0306(8) 0.0060(7) 0.0199(7) 0.0045(7) C6 0.0389(9) 0.0376(10) 0.0400(9) 0.0007(8) 0.0163(7) 0.0114(7) C7 0.0406(9) 0.0366(10) 0.0405(10) 0.0002(8) 0.0161(8) -0.0084(7) C8 0.0502(10) 0.0360(10) 0.0417(10) -0.0054(8) 0.0216(8) -0.0073(8) C9 0.0302(7) 0.0266(8) 0.0231(7) 0.0015(6) 0.0155(6) 0.0010(6) C10 0.0334(8) 0.0292(8) 0.0307(8) 0.0044(6) 0.0193(6) 0.0043(6) C11 0.0404(9) 0.0400(10) 0.0324(8) 0.0082(7) 0.0233(7) 0.0092(7) C12 0.0315(8) 0.0301(8) 0.0271(8) 0.0004(6) 0.0150(6) -0.0004(6) C13 0.0323(8) 0.0412(10) 0.0318(8) 0.0024(7) 0.0156(7) -0.0014(7) C14 0.0444(9) 0.0290(9) 0.0446(10) -0.0023(7) 0.0266(8) 0.0031(7) C15 0.0529(10) 0.0291(9) 0.0373(9) -0.0086(7) 0.0239(8) 0.0056(7) C16 0.0733(13) 0.0459(12) 0.0395(10) -0.0052(9) 0.0316(10) 0.0059(10) C17 0.098(2) 0.0552(14) 0.0370(11) -0.0032(10) 0.0259(12) 0.0208(13) C18 0.075(2) 0.0574(15) 0.0447(12) -0.0217(11) 0.0041(11) 0.0249(12) C19 0.0540(12) 0.0501(13) 0.074(2) -0.0313(12) 0.0189(11) -0.0032(10) C20 0.0561(12) 0.0331(10) 0.0525(11) -0.0108(9) 0.0241(9) -0.0039(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 C1 1.202(2) . ? O2 C1 1.343(2) . ? O2 C4 1.456(2) . ? O3 C3 1.423(2) . ? O3 C2 1.426(2) . ? O4 C3 1.406(2) . ? O4 C7 1.432(2) . ? O5 C4 1.399(2) . ? O5 C8 1.431(2) . ? O6 C11 1.214(2) . ? O7 C11 1.333(2) . ? O7 C13 1.456(2) . ? O8 C14 1.412(2) . ? C1 C2 1.518(2) . ? C2 C9 1.532(2) . ? C3 C5 1.515(2) . ? C3 C4 1.537(2) . ? C4 C6 1.515(2) . ? C9 C12 1.523(2) . ? C9 C10 1.550(2) . ? C10 C11 1.523(2) . ? C10 C14 1.548(2) . ? C12 C13 1.502(2) . ? C14 C15 1.514(3) . ? C15 C16 1.387(3) . ? C15 C20 1.389(3) . ? C16 C17 1.384(3) . ? C17 C18 1.370(4) . ? C18 C19 1.386(4) . ? C19 C20 1.386(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 C1 O2 C4 121.38(12) . . ? C3 O3 C2 113.41(10) . . ? C3 O4 C7 115.99(12) . . ? C4 O5 C8 116.02(12) . . ? C11 O7 C13 119.22(12) . . ? O1 C1 O2 118.72(14) . . ? O1 C1 C2 120.83(14) . . ? O2 C1 C2 120.40(13) . . ? O3 C2 C1 114.89(12) . . ? O3 C2 C9 107.72(11) . . ? C1 C2 C9 110.29(12) . . ? O4 C3 O3 110.97(12) . . ? O4 C3 C5 114.35(12) . . ? O3 C3 C5 105.57(11) . . ? O4 C3 C4 104.37(12) . . ? O3 C3 C4 108.67(12) . . ? C5 C3 C4 112.92(13) . . ? O5 C4 O2 108.43(12) . . ? O5 C4 C6 113.82(13) . . ? O2 C4 C6 105.19(12) . . ? O5 C4 C3 105.99(12) . . ? O2 C4 C3 109.73(12) . . ? C6 C4 C3 113.60(13) . . ? C12 C9 C2 111.81(12) . . ? C12 C9 C10 111.64(12) . . ? C2 C9 C10 110.44(12) . . ? C11 C10 C14 106.32(13) . . ? C11 C10 C9 116.21(13) . . ? C14 C10 C9 112.98(13) . . ? O6 C11 O7 117.7(2) . . ? O6 C11 C10 121.0(2) . . ? O7 C11 C10 121.34(14) . . ? C13 C12 C9 108.65(13) . . ? O7 C13 C12 110.83(13) . . ? O8 C14 C15 113.34(15) . . ? O8 C14 C10 105.33(13) . . ? C15 C14 C10 111.95(13) . . ? C16 C15 C20 119.2(2) . . ? C16 C15 C14 121.8(2) . . ? C20 C15 C14 118.9(2) . . ? C17 C16 C15 120.0(2) . . ? C18 C17 C16 120.6(2) . . ? C17 C18 C19 120.1(2) . . ? C18 C19 C20 119.6(2) . . ? C19 C20 C15 120.5(2) . . ? _refine_diff_density_max 0.489 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.095 data_sl0021 _database_code_depnum_ccdc_archive 'CCDC 171363' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O9' _chemical_formula_weight 437.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.4142(4) _cell_length_b 13.0225(13) _cell_length_c 12.6626(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.031(5) _cell_angle_gamma 90.00 _cell_volume 1057.52(16) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9377 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ? _exptl_special_details ; Differences in Friedel opposites not sufficient to determine absolute structure. Therefore, Friedel opposites merged and structure refined in P2(1). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 3619 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2913 _reflns_number_gt 2417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.7937P] 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 0.076(10) _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' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2913 _refine_ls_number_parameters 281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1661 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0379(6) 0.1733(3) 0.0572(3) 0.0384(9) Uani 1 1 d . . . O2 O 0.0723(6) 0.2485(3) 0.2029(3) 0.0331(8) Uani 1 1 d . . . O3 O 0.1655(5) 0.4287(3) 0.0915(2) 0.0269(8) Uani 1 1 d . . . O4 O -0.1287(5) 0.4297(3) 0.1949(3) 0.0338(9) Uani 1 1 d . . . O5 O 0.3785(5) 0.3367(3) 0.2428(3) 0.0334(8) Uani 1 1 d . . . O6 O 0.5741(7) 0.5272(3) -0.1432(3) 0.0499(11) Uani 1 1 d . . . O7 O 0.6542(6) 0.3656(3) -0.1249(3) 0.0408(10) Uani 1 1 d . . . O8 O -0.1091(7) 0.4871(4) -0.3921(4) 0.0666(15) Uani 1 1 d . . . O9 O 0.1441(7) 0.5719(5) -0.4525(4) 0.0660(15) Uani 1 1 d . . . N1 N 0.0596(7) 0.5282(4) -0.3815(3) 0.0358(11) Uani 1 1 d . . . C1 C 0.0350(7) 0.2492(4) 0.0985(4) 0.0276(11) Uani 1 1 d . . . C2 C 0.0813(7) 0.3441(4) 0.0327(3) 0.0250(10) Uani 1 1 d . . . H2A H -0.0528 0.3672 -0.0009 0.030 Uiso 1 1 calc R . . C3 C 0.0900(7) 0.4357(4) 0.1954(4) 0.0288(11) Uani 1 1 d . . . C4 C 0.1646(8) 0.3399(4) 0.2550(4) 0.0298(11) Uani 1 1 d . . . C5 C 0.1784(9) 0.5336(4) 0.2425(4) 0.0356(12) Uani 1 1 d . . . H5A H 0.3310 0.5316 0.2401 0.053 Uiso 1 1 calc R . . H5B H 0.1349 0.5398 0.3160 0.053 Uiso 1 1 calc R . . H5C H 0.1266 0.5927 0.2019 0.053 Uiso 1 1 calc R . . C6 C 0.0947(9) 0.3336(5) 0.3692(4) 0.0419(14) Uani 1 1 d . . . H6A H -0.0579 0.3371 0.3712 0.063 Uiso 1 1 calc R . . H6B H 0.1545 0.3911 0.4094 0.063 Uiso 1 1 calc R . . H6C H 0.1423 0.2687 0.4003 0.063 Uiso 1 1 calc R . . C7 C -0.2358(9) 0.5115(5) 0.1386(5) 0.0410(14) Uani 1 1 d . . . H7A H -0.3868 0.5008 0.1423 0.062 Uiso 1 1 calc R . . H7B H -0.1939 0.5113 0.0646 0.062 Uiso 1 1 calc R . . H7C H -0.1994 0.5776 0.1709 0.062 Uiso 1 1 calc R . . C8 C 0.4880(9) 0.2532(6) 0.2891(5) 0.0489(16) Uani 1 1 d . . . H8A H 0.6369 0.2597 0.2745 0.073 Uiso 1 1 calc R . . H8B H 0.4350 0.1886 0.2592 0.073 Uiso 1 1 calc R . . H8C H 0.4677 0.2534 0.3656 0.073 Uiso 1 1 calc R . . C9 C 0.2315(8) 0.3183(4) -0.0557(4) 0.0276(11) Uani 1 1 d . . . H9A H 0.1588 0.2693 -0.1047 0.033 Uiso 1 1 calc R . . C10 C 0.2825(8) 0.4167(4) -0.1199(4) 0.0318(12) Uani 1 1 d . . . H10A H 0.2197 0.4753 -0.0806 0.038 Uiso 1 1 calc R . . C11 C 0.5122(8) 0.4417(5) -0.1297(4) 0.0382(13) Uani 1 1 d . . . C12 C 0.4298(8) 0.2651(4) -0.0134(4) 0.0339(12) Uani 1 1 d . . . H12A H 0.4883 0.3036 0.0476 0.041 Uiso 1 1 calc R . . H12B H 0.3968 0.1945 0.0101 0.041 Uiso 1 1 calc R . . C13 C 0.5851(8) 0.2618(4) -0.1011(4) 0.0364(12) Uani 1 1 d . . . H13A H 0.7063 0.2192 -0.0795 0.044 Uiso 1 1 calc R . . H13B H 0.5200 0.2306 -0.1649 0.044 Uiso 1 1 calc R . . C14 C 0.1721(8) 0.4155(4) -0.2318(4) 0.0291(11) Uani 1 1 d . . . H14A H 0.0238 0.3946 -0.2213 0.035 Uiso 1 1 calc R . . C15 C 0.1694(9) 0.5250(4) -0.2761(4) 0.0373(12) Uani 1 1 d . . . H15A H 0.0976 0.5711 -0.2263 0.045 Uiso 1 1 calc R . . H15B H 0.3143 0.5499 -0.2834 0.045 Uiso 1 1 calc R . . C16 C 0.2671(7) 0.3382(4) -0.3071(4) 0.0278(11) Uani 1 1 d . . . C17 C 0.1657(8) 0.2471(4) -0.3288(4) 0.0320(11) Uani 1 1 d . . . H17A H 0.0300 0.2360 -0.3022 0.038 Uiso 1 1 calc R . . C18 C 0.2592(10) 0.1716(5) -0.3888(4) 0.0430(14) Uani 1 1 d . . . H18A H 0.1872 0.1091 -0.4026 0.052 Uiso 1 1 calc R . . C19 C 0.4547(10) 0.1861(5) -0.4286(4) 0.0440(15) Uani 1 1 d . . . H19A H 0.5197 0.1337 -0.4686 0.053 Uiso 1 1 calc R . . C20 C 0.5555(9) 0.2785(5) -0.4096(4) 0.0424(15) Uani 1 1 d . . . H20A H 0.6907 0.2892 -0.4369 0.051 Uiso 1 1 calc R . . C21 C 0.4633(8) 0.3550(4) -0.3518(4) 0.0326(12) Uani 1 1 d . . . H21A H 0.5321 0.4190 -0.3420 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 0.047(2) 0.033(2) 0.035(2) 0.0002(17) -0.0042(17) -0.0087(18) O2 0.045(2) 0.0271(19) 0.0268(19) 0.0021(15) -0.0022(15) -0.0020(17) O3 0.0350(18) 0.0209(18) 0.0249(17) -0.0011(15) 0.0050(13) -0.0035(15) O4 0.0316(18) 0.036(2) 0.0343(19) 0.0034(17) 0.0047(14) 0.0009(17) O5 0.0331(18) 0.031(2) 0.0355(19) 0.0017(16) -0.0028(14) 0.0021(16) O6 0.060(3) 0.038(2) 0.051(3) 0.006(2) -0.010(2) -0.027(2) O7 0.035(2) 0.052(3) 0.036(2) 0.0015(19) -0.0026(15) -0.0077(19) O8 0.046(3) 0.088(4) 0.065(3) 0.029(3) -0.015(2) -0.018(3) O9 0.057(3) 0.096(4) 0.045(3) 0.032(3) 0.001(2) -0.013(3) N1 0.037(3) 0.037(3) 0.034(2) 0.007(2) 0.0007(19) 0.002(2) C1 0.031(2) 0.024(3) 0.027(2) 0.001(2) -0.005(2) -0.001(2) C2 0.030(2) 0.021(2) 0.025(2) 0.001(2) -0.0020(18) -0.002(2) C3 0.032(3) 0.032(3) 0.023(2) -0.006(2) 0.0036(19) 0.004(2) C4 0.033(3) 0.027(3) 0.030(3) 0.001(2) -0.002(2) -0.005(2) C5 0.040(3) 0.028(3) 0.039(3) -0.001(2) 0.004(2) 0.001(2) C6 0.051(3) 0.044(3) 0.031(3) 0.001(3) 0.004(2) 0.000(3) C7 0.035(3) 0.039(3) 0.049(3) 0.000(3) -0.001(2) 0.010(3) C8 0.044(3) 0.061(4) 0.042(3) 0.004(3) -0.010(3) 0.012(3) C9 0.036(3) 0.016(2) 0.030(3) -0.0013(19) 0.001(2) 0.002(2) C10 0.043(3) 0.029(3) 0.023(2) -0.002(2) 0.002(2) -0.004(2) C11 0.041(3) 0.051(4) 0.022(3) -0.005(3) -0.004(2) -0.008(3) C12 0.042(3) 0.030(3) 0.030(3) -0.002(2) 0.003(2) 0.005(2) C13 0.040(3) 0.038(3) 0.032(3) -0.008(2) -0.002(2) 0.007(3) C14 0.032(3) 0.029(3) 0.027(2) 0.002(2) 0.003(2) -0.001(2) C15 0.052(3) 0.028(3) 0.031(3) -0.002(2) -0.004(2) -0.002(3) C16 0.024(2) 0.033(3) 0.025(2) -0.002(2) -0.0053(18) 0.003(2) C17 0.038(3) 0.031(3) 0.027(3) 0.003(2) 0.000(2) 0.001(2) C18 0.063(4) 0.033(3) 0.033(3) -0.003(2) -0.002(3) -0.002(3) C19 0.060(4) 0.047(4) 0.025(3) -0.009(2) 0.001(2) 0.017(3) C20 0.039(3) 0.059(4) 0.029(3) -0.001(3) 0.004(2) 0.010(3) C21 0.033(3) 0.040(3) 0.025(2) -0.002(2) 0.0003(19) -0.007(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 C1 1.208(6) . ? O2 C1 1.339(6) . ? O2 C4 1.479(6) . ? O3 C3 1.413(6) . ? O3 C2 1.430(6) . ? O4 C3 1.405(6) . ? O4 C7 1.448(7) . ? O5 C4 1.384(6) . ? O5 C8 1.416(7) . ? O6 C11 1.196(8) . ? O7 C11 1.346(7) . ? O7 C13 1.456(7) . ? O8 N1 1.212(6) . ? O9 N1 1.201(6) . ? N1 C15 1.499(7) . ? C1 C2 1.522(7) . ? C2 C9 1.528(7) . ? C2 H2A 1.0000 . ? C3 C5 1.513(8) . ? C3 C4 1.530(7) . ? C4 C6 1.524(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C12 1.537(7) . ? C9 C10 1.555(7) . ? C9 H9A 1.0000 . ? C10 C11 1.516(8) . ? C10 C14 1.573(7) . ? C10 H10A 1.0000 . ? C12 C13 1.506(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C16 1.521(7) . ? C14 C15 1.533(7) . ? C14 H14A 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.378(7) . ? C16 C21 1.406(7) . ? C17 C18 1.386(8) . ? C17 H17A 0.9500 . ? C18 C19 1.373(9) . ? C18 H18A 0.9500 . ? C19 C20 1.384(9) . ? C19 H19A 0.9500 . ? C20 C21 1.377(8) . ? C20 H20A 0.9500 . ? C21 H21A 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 C1 O2 C4 119.8(4) . . ? C3 O3 C2 113.7(4) . . ? C3 O4 C7 115.2(4) . . ? C4 O5 C8 117.5(4) . . ? C11 O7 C13 119.0(4) . . ? O9 N1 O8 122.7(5) . . ? O9 N1 C15 117.9(5) . . ? O8 N1 C15 119.4(5) . . ? O1 C1 O2 118.9(5) . . ? O1 C1 C2 120.3(4) . . ? O2 C1 C2 120.8(4) . . ? O3 C2 C1 114.6(4) . . ? O3 C2 C9 108.3(4) . . ? C1 C2 C9 110.8(4) . . ? O3 C2 H2A 107.6 . . ? C1 C2 H2A 107.6 . . ? C9 C2 H2A 107.6 . . ? O4 C3 O3 110.6(4) . . ? O4 C3 C5 114.5(4) . . ? O3 C3 C5 106.8(4) . . ? O4 C3 C4 105.1(4) . . ? O3 C3 C4 107.3(4) . . ? C5 C3 C4 112.4(4) . . ? O5 C4 O2 108.4(4) . . ? O5 C4 C6 114.4(4) . . ? O2 C4 C6 104.9(4) . . ? O5 C4 C3 105.7(4) . . ? O2 C4 C3 108.5(4) . . ? C6 C4 C3 114.7(4) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 C12 111.8(4) . . ? C2 C9 C10 110.1(4) . . ? C12 C9 C10 111.9(4) . . ? C2 C9 H9A 107.6 . . ? C12 C9 H9A 107.6 . . ? C10 C9 H9A 107.6 . . ? C11 C10 C9 115.7(4) . . ? C11 C10 C14 110.6(4) . . ? C9 C10 C14 111.5(4) . . ? C11 C10 H10A 106.1 . . ? C9 C10 H10A 106.1 . . ? C14 C10 H10A 106.1 . . ? O6 C11 O7 117.8(5) . . ? O6 C11 C10 122.5(6) . . ? O7 C11 C10 119.7(5) . . ? C13 C12 C9 108.1(4) . . ? C13 C12 H12A 110.1 . . ? C9 C12 H12A 110.1 . . ? C13 C12 H12B 110.1 . . ? C9 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? O7 C13 C12 109.5(4) . . ? O7 C13 H13A 109.8 . . ? C12 C13 H13A 109.8 . . ? O7 C13 H13B 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C16 C14 C15 112.9(4) . . ? C16 C14 C10 113.1(4) . . ? C15 C14 C10 108.8(4) . . ? C16 C14 H14A 107.3 . . ? C15 C14 H14A 107.3 . . ? C10 C14 H14A 107.3 . . ? N1 C15 C14 110.7(4) . . ? N1 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C21 118.5(5) . . ? C17 C16 C14 120.1(4) . . ? C21 C16 C14 121.4(5) . . ? C16 C17 C18 120.8(5) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C19 C18 C17 120.7(6) . . ? C19 C18 H18A 119.6 . . ? C17 C18 H18A 119.6 . . ? C18 C19 C20 118.8(5) . . ? C18 C19 H19A 120.6 . . ? C20 C19 H19A 120.6 . . ? C21 C20 C19 121.2(5) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C20 C21 C16 119.8(5) . . ? C20 C21 H21A 120.1 . . ? C16 C21 H21A 120.1 . . ? 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 C4 O2 C1 O1 179.0(5) . . . . ? C4 O2 C1 C2 -1.5(6) . . . . ? C3 O3 C2 C1 -33.1(5) . . . . ? C3 O3 C2 C9 -157.3(4) . . . . ? O1 C1 C2 O3 179.5(4) . . . . ? O2 C1 C2 O3 0.1(6) . . . . ? O1 C1 C2 C9 -57.6(6) . . . . ? O2 C1 C2 C9 122.9(5) . . . . ? C7 O4 C3 O3 -62.3(6) . . . . ? C7 O4 C3 C5 58.4(6) . . . . ? C7 O4 C3 C4 -177.8(4) . . . . ? C2 O3 C3 O4 -49.8(5) . . . . ? C2 O3 C3 C5 -175.0(4) . . . . ? C2 O3 C3 C4 64.3(5) . . . . ? C8 O5 C4 O2 -62.5(5) . . . . ? C8 O5 C4 C6 54.1(6) . . . . ? C8 O5 C4 C3 -178.7(4) . . . . ? C1 O2 C4 O5 -82.6(5) . . . . ? C1 O2 C4 C6 154.8(4) . . . . ? C1 O2 C4 C3 31.8(5) . . . . ? O4 C3 C4 O5 171.5(4) . . . . ? O3 C3 C4 O5 53.7(5) . . . . ? C5 C3 C4 O5 -63.4(5) . . . . ? O4 C3 C4 O2 55.4(4) . . . . ? O3 C3 C4 O2 -62.4(5) . . . . ? C5 C3 C4 O2 -179.5(4) . . . . ? O4 C3 C4 C6 -61.5(5) . . . . ? O3 C3 C4 C6 -179.2(4) . . . . ? C5 C3 C4 C6 63.7(5) . . . . ? O3 C2 C9 C12 73.3(5) . . . . ? C1 C2 C9 C12 -53.1(5) . . . . ? O3 C2 C9 C10 -51.8(5) . . . . ? C1 C2 C9 C10 -178.2(4) . . . . ? C2 C9 C10 C11 125.4(5) . . . . ? C12 C9 C10 C11 0.3(6) . . . . ? C2 C9 C10 C14 -107.1(5) . . . . ? C12 C9 C10 C14 127.8(5) . . . . ? C13 O7 C11 O6 175.7(5) . . . . ? C13 O7 C11 C10 -5.4(6) . . . . ? C9 C10 C11 O6 -154.0(5) . . . . ? C14 C10 C11 O6 78.1(6) . . . . ? C9 C10 C11 O7 27.2(6) . . . . ? C14 C10 C11 O7 -100.7(5) . . . . ? C2 C9 C12 C13 -168.9(4) . . . . ? C10 C9 C12 C13 -44.8(6) . . . . ? C11 O7 C13 C12 -42.7(6) . . . . ? C9 C12 C13 O7 67.6(5) . . . . ? C11 C10 C14 C16 58.7(6) . . . . ? C9 C10 C14 C16 -71.5(5) . . . . ? C11 C10 C14 C15 -67.6(6) . . . . ? C9 C10 C14 C15 162.2(4) . . . . ? O9 N1 C15 C14 -131.4(6) . . . . ? O8 N1 C15 C14 48.6(7) . . . . ? C16 C14 C15 N1 55.3(6) . . . . ? C10 C14 C15 N1 -178.3(4) . . . . ? C15 C14 C16 C17 -131.8(5) . . . . ? C10 C14 C16 C17 104.2(5) . . . . ? C15 C14 C16 C21 51.5(6) . . . . ? C10 C14 C16 C21 -72.6(6) . . . . ? C21 C16 C17 C18 3.2(7) . . . . ? C14 C16 C17 C18 -173.6(5) . . . . ? C16 C17 C18 C19 -0.4(9) . . . . ? C17 C18 C19 C20 -1.3(9) . . . . ? C18 C19 C20 C21 0.1(8) . . . . ? C19 C20 C21 C16 2.7(8) . . . . ? C17 C16 C21 C20 -4.3(7) . . . . ? C14 C16 C21 C20 172.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.366 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.094 data_sl0022 _database_code_depnum_ccdc_archive 'CCDC 171364' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H28 Cl N O9' _chemical_formula_weight 479.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 6.8253(2) _cell_length_b 12.1456(6) _cell_length_c 15.2031(12) _cell_angle_alpha 113.501(2) _cell_angle_beta 93.419(3) _cell_angle_gamma 92.824(5) _cell_volume 1150.02(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8210 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.218 _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 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13386 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5233 _reflns_number_gt 3525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.4679P] 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 5233 _refine_ls_number_parameters 307 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 0.80404(19) 0.15730(13) 0.24264(12) 0.0391(4) Uani 1 1 d . . . O2 O 0.73158(17) 0.33941(12) 0.26233(10) 0.0265(3) Uani 1 1 d . . . O3 O 0.35136(17) 0.29679(12) 0.30779(9) 0.0231(3) Uani 1 1 d . . . O4 O 0.37032(18) 0.31480(13) 0.16212(10) 0.0286(3) Uani 1 1 d . . . O5 O 0.60855(18) 0.48987(13) 0.39190(10) 0.0301(3) Uani 1 1 d . . . O6 O 0.0418(2) 0.14289(14) 0.48637(11) 0.0416(4) Uani 1 1 d . . . O7 O 0.3526(2) 0.15824(15) 0.53623(11) 0.0405(4) Uani 1 1 d . . . O8 O 0.0936(2) -0.27558(14) 0.28178(13) 0.0445(4) Uani 1 1 d . . . O9 O -0.1632(2) -0.25658(16) 0.20248(15) 0.0591(5) Uani 1 1 d . . . N1 N -0.0225(2) -0.21445(16) 0.26204(13) 0.0329(4) Uani 1 1 d . . . C1 C 0.6819(3) 0.23019(18) 0.26064(14) 0.0252(4) Uani 1 1 d . . . C2 C 0.4731(2) 0.19830(17) 0.27639(14) 0.0222(4) Uani 1 1 d . . . H2 H 0.4101 0.1366 0.2139 0.027 Uiso 1 1 calc R . . C3 C 0.3819(3) 0.37750(17) 0.26231(14) 0.0237(4) Uani 1 1 d . . . C4 C 0.5951(3) 0.43497(17) 0.29171(14) 0.0239(4) Uani 1 1 d . . . C5 C 0.2317(3) 0.46993(19) 0.29738(17) 0.0324(5) Uani 1 1 d . . . H5A H 0.2347 0.5212 0.2614 0.049 Uiso 1 1 calc R . . H5B H 0.2631 0.5197 0.3661 0.049 Uiso 1 1 calc R . . H5C H 0.1000 0.4286 0.2873 0.049 Uiso 1 1 calc R . . C6 C 0.6555(3) 0.5163(2) 0.24289(17) 0.0359(5) Uani 1 1 d . . . H6A H 0.5836 0.5890 0.2669 0.054 Uiso 1 1 calc R . . H6B H 0.6246 0.4738 0.1732 0.054 Uiso 1 1 calc R . . H6C H 0.7973 0.5389 0.2569 0.054 Uiso 1 1 calc R . . C7 C 0.1790(3) 0.2586(2) 0.11722(17) 0.0385(5) Uani 1 1 d . . . H7A H 0.1184 0.2209 0.1563 0.058 Uiso 1 1 calc R . . H7B H 0.1925 0.1971 0.0528 0.058 Uiso 1 1 calc R . . H7C H 0.0957 0.3196 0.1120 0.058 Uiso 1 1 calc R . . C8 C 0.7979(3) 0.5445(2) 0.43943(17) 0.0424(6) Uani 1 1 d . . . H8A H 0.8927 0.4829 0.4247 0.064 Uiso 1 1 calc R . . H8B H 0.7886 0.5820 0.5091 0.064 Uiso 1 1 calc R . . H8C H 0.8419 0.6061 0.4169 0.064 Uiso 1 1 calc R . . C9 C 0.4736(2) 0.14243(17) 0.35054(14) 0.0230(4) Uani 1 1 d . . . H9 H 0.5484 0.0689 0.3254 0.028 Uiso 1 1 calc R . . C10 C 0.2600(3) 0.10094(17) 0.36204(13) 0.0224(4) Uani 1 1 d . . . H10 H 0.1671 0.1388 0.3311 0.027 Uiso 1 1 calc R . . C11 C 0.2100(3) 0.13702(18) 0.46520(15) 0.0301(5) Uani 1 1 d . . . C12 C 0.5786(3) 0.22698(19) 0.44738(15) 0.0289(5) Uani 1 1 d . . . H12A H 0.7196 0.2413 0.4402 0.035 Uiso 1 1 calc R . . H12B H 0.5197 0.3054 0.4707 0.035 Uiso 1 1 calc R . . C13 C 0.5581(3) 0.1704(2) 0.51818(17) 0.0391(5) Uani 1 1 d . . . H13A H 0.6103 0.0900 0.4926 0.047 Uiso 1 1 calc R . . H13B H 0.6364 0.2207 0.5794 0.047 Uiso 1 1 calc R . . C14 C 0.2197(2) -0.03823(17) 0.30773(14) 0.0233(4) Uani 1 1 d . . . H14 H 0.3098 -0.0763 0.3397 0.028 Uiso 1 1 calc R . . C15 C 0.0072(3) -0.08104(18) 0.31425(16) 0.0299(5) Uani 1 1 d . . . H15A H -0.0181 -0.0575 0.3826 0.036 Uiso 1 1 calc R . . H15B H -0.0866 -0.0425 0.2855 0.036 Uiso 1 1 calc R . . C16 C 0.2653(3) -0.08147(17) 0.20326(14) 0.0236(4) Uani 1 1 d . . . C17 C 0.1577(3) -0.04916(18) 0.13780(15) 0.0283(4) Uani 1 1 d . . . H17 H 0.0501 -0.0008 0.1578 0.034 Uiso 1 1 calc R . . C18 C 0.2067(3) -0.0872(2) 0.04365(16) 0.0362(5) Uani 1 1 d . . . H18 H 0.1342 -0.0634 -0.0003 0.043 Uiso 1 1 calc R . . C19 C 0.3601(3) -0.1593(2) 0.01334(17) 0.0459(6) Uani 1 1 d . . . H19 H 0.3928 -0.1853 -0.0514 0.055 Uiso 1 1 calc R . . C20 C 0.4659(4) -0.1937(2) 0.07692(18) 0.0472(6) Uani 1 1 d . . . H20 H 0.5709 -0.2440 0.0561 0.057 Uiso 1 1 calc R . . C21 C 0.4186(3) -0.1546(2) 0.17143(16) 0.0354(5) Uani 1 1 d . . . H21 H 0.4922 -0.1782 0.2151 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.2730(4) 0.49708(17) 0.03740(17) 0.0934(6) Uani 0.50 1 d PD A -1 Cl2 Cl -0.1404(5) 0.4564(4) -0.0255(2) 0.1404(14) Uani 0.50 1 d PD A -1 C22 C 0.0704(14) 0.5405(10) -0.0056(9) 0.097(4) Uiso 0.50 1 d PD A -1 H22A H 0.0493 0.6230 0.0403 0.116 Uiso 0.50 1 calc PR A -1 H22B H 0.0995 0.5456 -0.0669 0.116 Uiso 0.50 1 calc PR A -1 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 0.0276(7) 0.0357(9) 0.0589(11) 0.0211(8) 0.0183(7) 0.0116(6) O2 0.0189(6) 0.0261(8) 0.0355(8) 0.0127(6) 0.0078(5) 0.0016(5) O3 0.0190(6) 0.0263(7) 0.0300(8) 0.0165(6) 0.0080(5) 0.0049(5) O4 0.0233(7) 0.0373(8) 0.0258(8) 0.0143(7) -0.0004(5) -0.0037(6) O5 0.0231(7) 0.0329(8) 0.0281(8) 0.0059(6) 0.0009(5) 0.0013(6) O6 0.0410(9) 0.0435(10) 0.0410(10) 0.0151(8) 0.0215(7) 0.0050(7) O7 0.0484(9) 0.0482(10) 0.0284(9) 0.0196(8) 0.0043(7) -0.0010(7) O8 0.0436(9) 0.0329(9) 0.0622(12) 0.0259(9) -0.0058(8) 0.0035(7) O9 0.0418(10) 0.0446(11) 0.0824(14) 0.0221(10) -0.0226(9) -0.0096(8) N1 0.0254(8) 0.0324(10) 0.0452(11) 0.0213(9) 0.0007(8) -0.0048(7) C1 0.0221(9) 0.0268(11) 0.0268(11) 0.0103(9) 0.0063(7) 0.0031(8) C2 0.0186(8) 0.0220(10) 0.0250(10) 0.0080(8) 0.0049(7) 0.0018(7) C3 0.0216(9) 0.0269(11) 0.0268(11) 0.0149(9) 0.0043(7) 0.0017(7) C4 0.0212(9) 0.0247(10) 0.0274(11) 0.0118(9) 0.0036(7) 0.0033(7) C5 0.0238(10) 0.0321(12) 0.0469(14) 0.0212(11) 0.0046(9) 0.0054(8) C6 0.0300(10) 0.0339(12) 0.0494(14) 0.0234(11) 0.0037(9) -0.0035(9) C7 0.0299(11) 0.0487(15) 0.0361(13) 0.0188(11) -0.0071(9) -0.0083(9) C8 0.0280(11) 0.0465(14) 0.0377(14) 0.0025(11) -0.0049(9) 0.0024(9) C9 0.0211(9) 0.0227(10) 0.0273(11) 0.0121(9) 0.0037(7) 0.0032(7) C10 0.0233(9) 0.0228(10) 0.0243(10) 0.0122(8) 0.0049(7) 0.0039(7) C11 0.0390(11) 0.0236(11) 0.0305(12) 0.0131(9) 0.0085(9) 0.0028(8) C12 0.0277(10) 0.0297(11) 0.0298(12) 0.0134(9) -0.0033(8) -0.0002(8) C13 0.0414(12) 0.0427(14) 0.0363(13) 0.0208(11) -0.0066(10) -0.0003(10) C14 0.0213(9) 0.0241(10) 0.0286(11) 0.0144(9) 0.0040(7) 0.0026(7) C15 0.0270(10) 0.0261(11) 0.0391(12) 0.0151(10) 0.0088(8) 0.0011(8) C16 0.0211(9) 0.0196(10) 0.0287(11) 0.0084(8) 0.0031(7) -0.0007(7) C17 0.0252(9) 0.0281(11) 0.0301(12) 0.0101(9) 0.0012(8) 0.0031(8) C18 0.0392(12) 0.0383(13) 0.0277(12) 0.0106(10) -0.0021(9) 0.0011(9) C19 0.0518(14) 0.0528(16) 0.0293(13) 0.0103(12) 0.0135(10) 0.0103(12) C20 0.0472(13) 0.0507(16) 0.0444(15) 0.0154(12) 0.0199(11) 0.0238(11) C21 0.0334(11) 0.0397(13) 0.0378(13) 0.0185(11) 0.0081(9) 0.0131(9) Cl1 0.1122(16) 0.0626(12) 0.1080(16) 0.0400(11) -0.0163(13) 0.0118(11) Cl2 0.104(2) 0.168(3) 0.103(2) 0.014(2) -0.0081(18) -0.032(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 C1 1.208(2) . ? O2 C1 1.343(2) . ? O2 C4 1.469(2) . ? O3 C3 1.421(2) . ? O3 C2 1.428(2) . ? O4 C3 1.400(2) . ? O4 C7 1.439(2) . ? O5 C4 1.393(2) . ? O5 C8 1.433(2) . ? O6 C11 1.209(2) . ? O7 C11 1.344(3) . ? O7 C13 1.457(3) . ? O8 N1 1.215(2) . ? O9 N1 1.217(2) . ? N1 C15 1.490(3) . ? C1 C2 1.517(2) . ? C2 C9 1.530(3) . ? C2 H2 1.0000 . ? C3 C5 1.516(3) . ? C3 C4 1.542(2) . ? C4 C6 1.509(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C12 1.527(3) . ? C9 C10 1.561(2) . ? C9 H9 1.0000 . ? C10 C11 1.516(3) . ? C10 C14 1.558(3) . ? C10 H10 1.0000 . ? C12 C13 1.500(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C16 1.518(3) . ? C14 C15 1.539(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.388(3) . ? C16 C17 1.392(3) . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.379(3) . ? C18 H18 0.9500 . ? C19 C20 1.378(3) . ? C19 H19 0.9500 . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? Cl1 C22 1.690(9) . ? Cl2 C22 1.662(9) . ? C22 H22A 0.9900 . ? C22 H22B 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 C1 O2 C4 121.19(13) . . ? C3 O3 C2 113.23(13) . . ? C3 O4 C7 115.48(14) . . ? C4 O5 C8 116.78(15) . . ? C11 O7 C13 119.74(16) . . ? O8 N1 O9 123.42(19) . . ? O8 N1 C15 118.36(17) . . ? O9 N1 C15 118.21(17) . . ? O1 C1 O2 118.76(16) . . ? O1 C1 C2 121.23(18) . . ? O2 C1 C2 119.95(15) . . ? O3 C2 C1 115.01(15) . . ? O3 C2 C9 107.51(14) . . ? C1 C2 C9 110.56(15) . . ? O3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C9 C2 H2 107.8 . . ? O4 C3 O3 110.69(15) . . ? O4 C3 C5 114.12(16) . . ? O3 C3 C5 106.41(14) . . ? O4 C3 C4 105.47(14) . . ? O3 C3 C4 107.88(14) . . ? C5 C3 C4 112.19(16) . . ? O5 C4 O2 108.61(14) . . ? O5 C4 C6 114.99(17) . . ? O2 C4 C6 104.86(14) . . ? O5 C4 C3 104.87(14) . . ? O2 C4 C3 109.12(15) . . ? C6 C4 C3 114.25(16) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C9 C2 112.06(16) . . ? C12 C9 C10 111.37(15) . . ? C2 C9 C10 111.02(14) . . ? C12 C9 H9 107.4 . . ? C2 C9 H9 107.4 . . ? C10 C9 H9 107.4 . . ? C11 C10 C14 108.61(15) . . ? C11 C10 C9 114.94(16) . . ? C14 C10 C9 110.78(14) . . ? C11 C10 H10 107.4 . . ? C14 C10 H10 107.4 . . ? C9 C10 H10 107.4 . . ? O6 C11 O7 117.43(18) . . ? O6 C11 C10 121.84(19) . . ? O7 C11 C10 120.66(17) . . ? C13 C12 C9 108.83(17) . . ? C13 C12 H12A 109.9 . . ? C9 C12 H12A 109.9 . . ? C13 C12 H12B 109.9 . . ? C9 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? O7 C13 C12 110.80(17) . . ? O7 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? O7 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C16 C14 C15 110.36(16) . . ? C16 C14 C10 111.78(15) . . ? C15 C14 C10 111.89(15) . . ? C16 C14 H14 107.5 . . ? C15 C14 H14 107.5 . . ? C10 C14 H14 107.5 . . ? N1 C15 C14 109.60(15) . . ? N1 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? N1 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? C21 C16 C17 118.56(18) . . ? C21 C16 C14 119.73(18) . . ? C17 C16 C14 121.70(16) . . ? C18 C17 C16 120.28(18) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 120.0(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.7(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C16 121.1(2) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? Cl2 C22 Cl1 118.3(7) . . ? Cl2 C22 H22A 107.7 . . ? Cl1 C22 H22A 107.7 . . ? Cl2 C22 H22B 107.7 . . ? Cl1 C22 H22B 107.7 . . ? H22A C22 H22B 107.1 . . ? 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 C4 O2 C1 O1 -174.77(17) . . . . ? C4 O2 C1 C2 8.1(3) . . . . ? C3 O3 C2 C1 39.2(2) . . . . ? C3 O3 C2 C9 162.81(14) . . . . ? O1 C1 C2 O3 173.16(18) . . . . ? O2 C1 C2 O3 -9.8(2) . . . . ? O1 C1 C2 C9 51.2(2) . . . . ? O2 C1 C2 C9 -131.80(18) . . . . ? C7 O4 C3 O3 67.0(2) . . . . ? C7 O4 C3 C5 -53.0(2) . . . . ? C7 O4 C3 C4 -176.62(16) . . . . ? C2 O3 C3 O4 51.11(18) . . . . ? C2 O3 C3 C5 175.61(15) . . . . ? C2 O3 C3 C4 -63.81(19) . . . . ? C8 O5 C4 O2 59.5(2) . . . . ? C8 O5 C4 C6 -57.6(2) . . . . ? C8 O5 C4 C3 176.07(17) . . . . ? C1 O2 C4 O5 81.85(19) . . . . ? C1 O2 C4 C6 -154.74(17) . . . . ? C1 O2 C4 C3 -31.9(2) . . . . ? O4 C3 C4 O5 -175.97(14) . . . . ? O3 C3 C4 O5 -57.65(18) . . . . ? C5 C3 C4 O5 59.2(2) . . . . ? O4 C3 C4 O2 -59.77(18) . . . . ? O3 C3 C4 O2 58.55(18) . . . . ? C5 C3 C4 O2 175.43(15) . . . . ? O4 C3 C4 C6 57.2(2) . . . . ? O3 C3 C4 C6 175.54(16) . . . . ? C5 C3 C4 C6 -67.6(2) . . . . ? O3 C2 C9 C12 -67.53(18) . . . . ? C1 C2 C9 C12 58.8(2) . . . . ? O3 C2 C9 C10 57.71(19) . . . . ? C1 C2 C9 C10 -176.01(15) . . . . ? C12 C9 C10 C11 -8.1(2) . . . . ? C2 C9 C10 C11 -133.72(17) . . . . ? C12 C9 C10 C14 -131.67(16) . . . . ? C2 C9 C10 C14 102.71(18) . . . . ? C13 O7 C11 O6 -170.75(18) . . . . ? C13 O7 C11 C10 12.3(3) . . . . ? C14 C10 C11 O6 -77.0(2) . . . . ? C9 C10 C11 O6 158.29(18) . . . . ? C14 C10 C11 O7 99.8(2) . . . . ? C9 C10 C11 O7 -24.9(3) . . . . ? C2 C9 C12 C13 175.27(16) . . . . ? C10 C9 C12 C13 50.2(2) . . . . ? C11 O7 C13 C12 33.1(3) . . . . ? C9 C12 C13 O7 -64.5(2) . . . . ? C11 C10 C14 C16 179.66(15) . . . . ? C9 C10 C14 C16 -53.2(2) . . . . ? C11 C10 C14 C15 55.3(2) . . . . ? C9 C10 C14 C15 -177.57(16) . . . . ? O8 N1 C15 C14 52.1(2) . . . . ? O9 N1 C15 C14 -128.6(2) . . . . ? C16 C14 C15 N1 55.4(2) . . . . ? C10 C14 C15 N1 -179.48(16) . . . . ? C15 C14 C16 C21 -120.6(2) . . . . ? C10 C14 C16 C21 114.2(2) . . . . ? C15 C14 C16 C17 59.8(2) . . . . ? C10 C14 C16 C17 -65.4(2) . . . . ? C21 C16 C17 C18 -1.6(3) . . . . ? C14 C16 C17 C18 178.07(18) . . . . ? C16 C17 C18 C19 1.3(3) . . . . ? C17 C18 C19 C20 -0.2(4) . . . . ? C18 C19 C20 C21 -0.6(4) . . . . ? C19 C20 C21 C16 0.3(4) . . . . ? C17 C16 C21 C20 0.8(3) . . . . ? C14 C16 C21 C20 -178.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.326 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.051 data_sl0026 _database_code_depnum_ccdc_archive 'CCDC 171365' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 O8' _chemical_formula_weight 544.58 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)/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 12.0281(6) _cell_length_b 17.7690(9) _cell_length_c 14.0771(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.804(3) _cell_angle_gamma 90.00 _cell_volume 2731.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 17454 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 1.033 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 17814 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6175 _reflns_number_gt 4431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+1.3752P] 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 6175 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 0.11905(12) -0.24930(7) 0.25390(11) 0.0389(3) Uani 1 1 d . . . O2 O -0.03134(12) -0.24838(7) 0.30335(10) 0.0334(3) Uani 1 1 d . . . O3 O -0.09767(11) -0.10263(6) 0.22396(9) 0.0272(3) Uani 1 1 d . . . O4 O -0.22148(11) -0.20044(7) 0.12608(9) 0.0326(3) Uani 1 1 d . . . O5 O -0.09394(13) -0.16386(7) 0.39761(10) 0.0367(3) Uani 1 1 d . . . O6 O -0.08336(12) 0.07937(7) 0.21259(10) 0.0365(3) Uani 1 1 d . . . O7 O 0.03219(11) 0.03062(7) 0.36520(9) 0.0317(3) Uani 1 1 d . . . O8 O 0.04178(12) 0.11749(7) 0.04266(10) 0.0345(3) Uani 1 1 d . . . C1 C 0.03553(17) -0.21499(10) 0.25928(14) 0.0285(4) Uani 1 1 d . . . C2 C 0.00391(16) -0.13639(9) 0.21377(14) 0.0257(4) Uani 1 1 d . . . H2 H -0.0166 -0.1399 0.1373 0.031 Uiso 1 1 calc R . . C3 C -0.19070(16) -0.15499(10) 0.21536(14) 0.0288(4) Uani 1 1 d . . . C4 C -0.13648(17) -0.20941(10) 0.30876(15) 0.0314(4) Uani 1 1 d . . . C5 C -0.29631(18) -0.10899(11) 0.21539(17) 0.0386(5) Uani 1 1 d . . . H5A H -0.3150 -0.0682 0.1642 0.058 Uiso 1 1 calc R . . H5B H -0.2740 -0.0877 0.2852 0.058 Uiso 1 1 calc R . . H5C H -0.3684 -0.1413 0.1968 0.058 Uiso 1 1 calc R . . C6 C -0.2221(2) -0.27146(12) 0.30867(18) 0.0438(5) Uani 1 1 d . . . H6A H -0.1762 -0.3094 0.3611 0.066 Uiso 1 1 calc R . . H6B H -0.2587 -0.2949 0.2393 0.066 Uiso 1 1 calc R . . H6C H -0.2869 -0.2504 0.3256 0.066 Uiso 1 1 calc R . . C7 C -0.27761(19) -0.16211(12) 0.02773(15) 0.0405(5) Uani 1 1 d . . . H7A H -0.3611 -0.1474 0.0152 0.061 Uiso 1 1 calc R . . H7B H -0.2802 -0.1956 -0.0284 0.061 Uiso 1 1 calc R . . H7C H -0.2298 -0.1171 0.0292 0.061 Uiso 1 1 calc R . . C8 C -0.0412(2) -0.20062(14) 0.49747(17) 0.0535(6) Uani 1 1 d . . . H8A H -0.1047 -0.2293 0.5081 0.080 Uiso 1 1 calc R . . H8B H -0.0066 -0.1628 0.5529 0.080 Uiso 1 1 calc R . . H8C H 0.0237 -0.2349 0.4997 0.080 Uiso 1 1 calc R . . C9 C 0.11359(15) -0.08280(9) 0.26293(12) 0.0235(4) Uani 1 1 d . . . H9 H 0.1808 -0.1016 0.2450 0.028 Uiso 1 1 calc R . . C10 C 0.07697(15) -0.00322(9) 0.21560(13) 0.0245(4) Uani 1 1 d . . . H10 H 0.0282 -0.0084 0.1384 0.029 Uiso 1 1 calc R . . C11 C -0.00073(16) 0.03740(10) 0.26040(14) 0.0274(4) Uani 1 1 d . . . C12 C 0.16286(15) -0.07762(10) 0.38090(13) 0.0266(4) Uani 1 1 d . . . C13 C 0.12053(16) -0.02160(10) 0.42592(14) 0.0283(4) Uani 1 1 d . . . C14 C 0.16044(18) -0.01443(11) 0.53292(14) 0.0347(4) Uani 1 1 d . . . H14 H 0.1299 0.0246 0.5615 0.042 Uiso 1 1 calc R . . C15 C 0.24580(19) -0.06523(12) 0.59778(15) 0.0403(5) Uani 1 1 d . . . H15 H 0.2722 -0.0620 0.6714 0.048 Uiso 1 1 calc R . . C16 C 0.29285(19) -0.12061(11) 0.55627(15) 0.0392(5) Uani 1 1 d . . . H16 H 0.3530 -0.1545 0.6012 0.047 Uiso 1 1 calc R . . C17 C 0.25157(17) -0.12641(10) 0.44811(14) 0.0323(4) Uani 1 1 d . . . H17 H 0.2845 -0.1643 0.4197 0.039 Uiso 1 1 calc R . . C18 C 0.19233(16) 0.04489(9) 0.23486(13) 0.0263(4) Uani 1 1 d . . . H18 H 0.2496 0.0362 0.3097 0.032 Uiso 1 1 calc R . . C19 C 0.16639(17) 0.13012(10) 0.22523(14) 0.0293(4) Uani 1 1 d . . . H19A H 0.1360 0.1445 0.2780 0.035 Uiso 1 1 calc R . . H19B H 0.2448 0.1569 0.2430 0.035 Uiso 1 1 calc R . . C20 C 0.07581(16) 0.15750(10) 0.11991(14) 0.0276(4) Uani 1 1 d . . . C21 C 0.03156(16) 0.23721(10) 0.11211(14) 0.0308(4) Uani 1 1 d . . . C22 C 0.07623(18) 0.28691(11) 0.19647(15) 0.0349(4) Uani 1 1 d . . . H22 H 0.1359 0.2702 0.2622 0.042 Uiso 1 1 calc R . . C23 C 0.0344(2) 0.36016(12) 0.18516(17) 0.0414(5) Uani 1 1 d . . . H23 H 0.0657 0.3936 0.2431 0.050 Uiso 1 1 calc R . . C24 C -0.0520(2) 0.38480(13) 0.09090(19) 0.0524(6) Uani 1 1 d . . . H24 H -0.0805 0.4353 0.0833 0.063 Uiso 1 1 calc R . . C25 C -0.0974(3) 0.33596(14) 0.00705(19) 0.0629(7) Uani 1 1 d . . . H25 H -0.1577 0.3528 -0.0583 0.076 Uiso 1 1 calc R . . C26 C -0.0554(2) 0.26274(12) 0.01781(16) 0.0479(5) Uani 1 1 d . . . H26 H -0.0868 0.2296 -0.0405 0.058 Uiso 1 1 calc R . . C27 C 0.26138(15) 0.01902(9) 0.17095(13) 0.0261(4) Uani 1 1 d . . . C28 C 0.21354(17) -0.03051(11) 0.08756(14) 0.0315(4) Uani 1 1 d . . . H28 H 0.1323 -0.0486 0.0661 0.038 Uiso 1 1 calc R . . C29 C 0.28256(18) -0.05422(12) 0.03469(15) 0.0374(4) Uani 1 1 d . . . H29 H 0.2482 -0.0883 -0.0223 0.045 Uiso 1 1 calc R . . C30 C 0.40038(18) -0.02840(12) 0.06474(16) 0.0386(5) Uani 1 1 d . . . H30 H 0.4482 -0.0454 0.0297 0.046 Uiso 1 1 calc R . . C31 C 0.44890(18) 0.02264(11) 0.14657(16) 0.0378(5) Uani 1 1 d . . . H31 H 0.5293 0.0417 0.1664 0.045 Uiso 1 1 calc R . . C32 C 0.38032(17) 0.04573(10) 0.19921(15) 0.0321(4) Uani 1 1 d . . . H32 H 0.4146 0.0803 0.2555 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 0.0401(8) 0.0273(7) 0.0564(9) 0.0003(6) 0.0271(7) 0.0070(6) O2 0.0400(8) 0.0244(6) 0.0423(8) 0.0061(5) 0.0237(6) 0.0051(6) O3 0.0254(6) 0.0213(6) 0.0370(7) -0.0013(5) 0.0151(5) -0.0008(5) O4 0.0360(7) 0.0271(7) 0.0328(7) -0.0038(5) 0.0127(6) -0.0047(5) O5 0.0477(8) 0.0328(7) 0.0326(7) 0.0005(6) 0.0198(6) 0.0023(6) O6 0.0347(7) 0.0335(7) 0.0410(8) 0.0064(6) 0.0156(6) 0.0096(6) O7 0.0363(7) 0.0307(7) 0.0311(7) 0.0011(5) 0.0170(6) 0.0067(6) O8 0.0399(8) 0.0304(7) 0.0304(7) -0.0049(6) 0.0118(6) -0.0043(6) C1 0.0316(10) 0.0233(9) 0.0326(9) -0.0033(7) 0.0155(8) -0.0013(7) C2 0.0280(9) 0.0234(8) 0.0288(9) -0.0018(7) 0.0150(7) 0.0003(7) C3 0.0282(9) 0.0252(9) 0.0352(10) -0.0035(7) 0.0154(8) -0.0048(7) C4 0.0357(10) 0.0273(9) 0.0372(10) -0.0003(8) 0.0211(8) 0.0009(8) C5 0.0314(10) 0.0376(11) 0.0494(12) -0.0027(9) 0.0195(9) 0.0021(9) C6 0.0489(13) 0.0378(11) 0.0535(13) 0.0030(10) 0.0301(11) -0.0077(10) C7 0.0428(12) 0.0387(11) 0.0351(10) 0.0017(9) 0.0114(9) -0.0055(9) C8 0.0718(17) 0.0503(14) 0.0397(12) 0.0035(10) 0.0248(11) 0.0093(12) C9 0.0244(9) 0.0217(8) 0.0264(8) 0.0020(7) 0.0125(7) 0.0012(7) C10 0.0268(9) 0.0227(8) 0.0248(8) 0.0007(7) 0.0117(7) -0.0014(7) C11 0.0295(9) 0.0231(8) 0.0307(9) 0.0004(7) 0.0137(7) -0.0025(7) C12 0.0252(9) 0.0250(9) 0.0284(9) 0.0006(7) 0.0103(7) -0.0034(7) C13 0.0290(9) 0.0273(9) 0.0303(9) 0.0022(7) 0.0141(7) -0.0013(7) C14 0.0395(11) 0.0362(10) 0.0307(10) -0.0039(8) 0.0169(8) -0.0045(9) C15 0.0474(12) 0.0431(11) 0.0251(9) 0.0017(8) 0.0101(9) -0.0062(10) C16 0.0400(11) 0.0375(11) 0.0318(10) 0.0086(8) 0.0069(8) 0.0025(9) C17 0.0346(10) 0.0267(9) 0.0347(10) 0.0030(8) 0.0136(8) 0.0013(8) C18 0.0262(9) 0.0260(9) 0.0258(9) 0.0007(7) 0.0101(7) -0.0038(7) C19 0.0321(10) 0.0259(9) 0.0300(9) -0.0021(7) 0.0131(8) -0.0062(8) C20 0.0280(9) 0.0274(9) 0.0302(9) -0.0042(7) 0.0151(7) -0.0086(7) C21 0.0297(10) 0.0307(9) 0.0336(10) 0.0017(8) 0.0150(8) 0.0004(8) C22 0.0350(10) 0.0327(10) 0.0363(10) -0.0006(8) 0.0143(8) -0.0012(8) C23 0.0431(12) 0.0359(11) 0.0484(12) -0.0092(9) 0.0226(10) -0.0006(9) C24 0.0594(15) 0.0354(12) 0.0639(15) 0.0025(11) 0.0273(12) 0.0163(11) C25 0.0735(18) 0.0529(14) 0.0429(13) 0.0077(11) 0.0052(12) 0.0242(13) C26 0.0545(14) 0.0445(12) 0.0342(11) -0.0048(9) 0.0082(10) 0.0083(11) C27 0.0265(9) 0.0242(8) 0.0282(9) 0.0052(7) 0.0123(7) 0.0008(7) C28 0.0271(9) 0.0356(10) 0.0314(10) 0.0012(8) 0.0119(8) -0.0031(8) C29 0.0391(11) 0.0445(11) 0.0311(10) -0.0009(9) 0.0171(8) 0.0022(9) C30 0.0351(11) 0.0482(12) 0.0404(11) 0.0093(9) 0.0234(9) 0.0085(9) C31 0.0278(10) 0.0398(11) 0.0471(12) 0.0082(9) 0.0171(9) -0.0011(8) C32 0.0297(10) 0.0292(9) 0.0357(10) 0.0030(8) 0.0120(8) -0.0029(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 C1 1.204(2) . ? O2 C1 1.343(2) . ? O2 C4 1.472(2) . ? O3 C3 1.421(2) . ? O3 C2 1.421(2) . ? O4 C3 1.407(2) . ? O4 C7 1.433(2) . ? O5 C4 1.394(2) . ? O5 C8 1.434(2) . ? O6 C11 1.198(2) . ? O7 C11 1.363(2) . ? O7 C13 1.400(2) . ? O8 C20 1.217(2) . ? C1 C2 1.517(2) . ? C2 C9 1.536(2) . ? C2 H2 1.0000 . ? C3 C5 1.511(3) . ? C3 C4 1.539(3) . ? C4 C6 1.508(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C12 1.514(2) . ? C9 C10 1.546(2) . ? C9 H9 1.0000 . ? C10 C11 1.512(2) . ? C10 C18 1.554(2) . ? C10 H10 1.0000 . ? C12 C13 1.386(2) . ? C12 C17 1.392(2) . ? C13 C14 1.382(2) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.381(3) . ? C15 H15 0.9500 . ? C16 C17 1.393(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C27 1.529(2) . ? C18 C19 1.541(2) . ? C18 H18 1.0000 . ? C19 C20 1.505(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.501(3) . ? C21 C26 1.377(3) . ? C21 C22 1.394(3) . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 C24 1.369(3) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 C26 1.381(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.384(2) . ? C27 C32 1.397(2) . ? C28 C29 1.393(3) . ? C28 H28 0.9500 . ? C29 C30 1.377(3) . ? C29 H29 0.9500 . ? C30 C31 1.388(3) . ? C30 H30 0.9500 . ? C31 C32 1.382(3) . ? C31 H31 0.9500 . ? C32 H32 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 C1 O2 C4 120.69(13) . . ? C3 O3 C2 113.24(12) . . ? C3 O4 C7 115.54(14) . . ? C4 O5 C8 117.38(15) . . ? C11 O7 C13 121.40(13) . . ? O1 C1 O2 118.85(16) . . ? O1 C1 C2 120.50(16) . . ? O2 C1 C2 120.62(15) . . ? O3 C2 C1 114.82(14) . . ? O3 C2 C9 107.76(13) . . ? C1 C2 C9 111.39(14) . . ? O3 C2 H2 107.5 . . ? C1 C2 H2 107.5 . . ? C9 C2 H2 107.5 . . ? O4 C3 O3 110.78(13) . . ? O4 C3 C5 113.87(15) . . ? O3 C3 C5 106.13(14) . . ? O4 C3 C4 105.12(14) . . ? O3 C3 C4 107.59(14) . . ? C5 C3 C4 113.25(15) . . ? O5 C4 O2 108.64(14) . . ? O5 C4 C6 114.74(16) . . ? O2 C4 C6 104.90(15) . . ? O5 C4 C3 105.43(14) . . ? O2 C4 C3 108.47(14) . . ? C6 C4 C3 114.46(16) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C9 C2 113.50(13) . . ? C12 C9 C10 109.07(13) . . ? C2 C9 C10 109.71(13) . . ? C12 C9 H9 108.1 . . ? C2 C9 H9 108.1 . . ? C10 C9 H9 108.1 . . ? C11 C10 C9 111.77(13) . . ? C11 C10 C18 109.12(13) . . ? C9 C10 C18 110.84(13) . . ? C11 C10 H10 108.3 . . ? C9 C10 H10 108.3 . . ? C18 C10 H10 108.3 . . ? O6 C11 O7 117.31(16) . . ? O6 C11 C10 125.10(16) . . ? O7 C11 C10 117.36(15) . . ? C13 C12 C17 117.40(16) . . ? C13 C12 C9 119.69(15) . . ? C17 C12 C9 122.91(16) . . ? C14 C13 C12 122.57(17) . . ? C14 C13 O7 115.61(16) . . ? C12 C13 O7 121.81(15) . . ? C13 C14 C15 118.77(18) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C16 C15 C14 120.51(18) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 119.58(18) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 121.11(18) . . ? C12 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C27 C18 C19 112.56(14) . . ? C27 C18 C10 113.44(14) . . ? C19 C18 C10 113.10(14) . . ? C27 C18 H18 105.6 . . ? C19 C18 H18 105.6 . . ? C10 C18 H18 105.6 . . ? C20 C19 C18 116.14(15) . . ? C20 C19 H19A 108.3 . . ? C18 C19 H19A 108.3 . . ? C20 C19 H19B 108.3 . . ? C18 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? O8 C20 C21 120.64(17) . . ? O8 C20 C19 121.62(16) . . ? C21 C20 C19 117.71(15) . . ? C26 C21 C22 118.54(18) . . ? C26 C21 C20 118.95(17) . . ? C22 C21 C20 122.51(17) . . ? C23 C22 C21 120.50(19) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.7(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C21 C26 C25 120.7(2) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C28 C27 C32 117.97(16) . . ? C28 C27 C18 123.70(15) . . ? C32 C27 C18 118.32(15) . . ? C27 C28 C29 121.11(17) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C30 C29 C28 120.17(19) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 119.54(18) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C32 C31 C30 120.09(18) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C27 121.09(18) . . ? C31 C32 H32 119.5 . . ? C27 C32 H32 119.5 . . ? 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 C4 O2 C1 O1 -178.17(16) . . . . ? C4 O2 C1 C2 -0.2(2) . . . . ? C3 O3 C2 C1 -34.95(19) . . . . ? C3 O3 C2 C9 -159.70(13) . . . . ? O1 C1 C2 O3 179.11(15) . . . . ? O2 C1 C2 O3 1.2(2) . . . . ? O1 C1 C2 C9 -58.1(2) . . . . ? O2 C1 C2 C9 123.97(17) . . . . ? C7 O4 C3 O3 -65.71(19) . . . . ? C7 O4 C3 C5 53.8(2) . . . . ? C7 O4 C3 C4 178.35(14) . . . . ? C2 O3 C3 O4 -49.55(18) . . . . ? C2 O3 C3 C5 -173.64(14) . . . . ? C2 O3 C3 C4 64.85(17) . . . . ? C8 O5 C4 O2 -65.7(2) . . . . ? C8 O5 C4 C6 51.3(2) . . . . ? C8 O5 C4 C3 178.23(16) . . . . ? C1 O2 C4 O5 -85.03(18) . . . . ? C1 O2 C4 C6 151.83(16) . . . . ? C1 O2 C4 C3 29.1(2) . . . . ? O4 C3 C4 O5 173.92(13) . . . . ? O3 C3 C4 O5 55.80(17) . . . . ? C5 C3 C4 O5 -61.17(19) . . . . ? O4 C3 C4 O2 57.70(17) . . . . ? O3 C3 C4 O2 -60.42(17) . . . . ? C5 C3 C4 O2 -177.39(14) . . . . ? O4 C3 C4 C6 -59.03(19) . . . . ? O3 C3 C4 C6 -177.15(15) . . . . ? C5 C3 C4 C6 65.9(2) . . . . ? O3 C2 C9 C12 69.87(17) . . . . ? C1 C2 C9 C12 -56.92(18) . . . . ? O3 C2 C9 C10 -52.42(17) . . . . ? C1 C2 C9 C10 -179.20(13) . . . . ? C12 C9 C10 C11 -48.48(18) . . . . ? C2 C9 C10 C11 76.40(17) . . . . ? C12 C9 C10 C18 73.49(16) . . . . ? C2 C9 C10 C18 -161.63(13) . . . . ? C13 O7 C11 O6 174.58(15) . . . . ? C13 O7 C11 C10 -10.7(2) . . . . ? C9 C10 C11 O6 -144.32(17) . . . . ? C18 C10 C11 O6 92.7(2) . . . . ? C9 C10 C11 O7 41.4(2) . . . . ? C18 C10 C11 O7 -81.54(17) . . . . ? C2 C9 C12 C13 -93.08(19) . . . . ? C10 C9 C12 C13 29.6(2) . . . . ? C2 C9 C12 C17 87.9(2) . . . . ? C10 C9 C12 C17 -149.45(16) . . . . ? C17 C12 C13 C14 -1.9(3) . . . . ? C9 C12 C13 C14 179.07(16) . . . . ? C17 C12 C13 O7 179.47(15) . . . . ? C9 C12 C13 O7 0.4(2) . . . . ? C11 O7 C13 C14 169.59(15) . . . . ? C11 O7 C13 C12 -11.7(2) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? O7 C13 C14 C15 178.58(16) . . . . ? C13 C14 C15 C16 1.9(3) . . . . ? C14 C15 C16 C17 -1.6(3) . . . . ? C13 C12 C17 C16 2.2(3) . . . . ? C9 C12 C17 C16 -178.80(17) . . . . ? C15 C16 C17 C12 -0.5(3) . . . . ? C11 C10 C18 C27 -166.24(14) . . . . ? C9 C10 C18 C27 70.25(17) . . . . ? C11 C10 C18 C19 -36.48(19) . . . . ? C9 C10 C18 C19 -159.99(14) . . . . ? C27 C18 C19 C20 68.49(19) . . . . ? C10 C18 C19 C20 -61.7(2) . . . . ? C18 C19 C20 O8 -12.5(2) . . . . ? C18 C19 C20 C21 169.62(15) . . . . ? O8 C20 C21 C26 4.9(3) . . . . ? C19 C20 C21 C26 -177.16(18) . . . . ? O8 C20 C21 C22 -174.28(17) . . . . ? C19 C20 C21 C22 3.7(3) . . . . ? C26 C21 C22 C23 -0.3(3) . . . . ? C20 C21 C22 C23 178.84(17) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C22 C23 C24 C25 0.1(4) . . . . ? C23 C24 C25 C26 -0.4(4) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? C20 C21 C26 C25 -179.2(2) . . . . ? C24 C25 C26 C21 0.4(4) . . . . ? C19 C18 C27 C28 -116.31(18) . . . . ? C10 C18 C27 C28 13.7(2) . . . . ? C19 C18 C27 C32 64.9(2) . . . . ? C10 C18 C27 C32 -165.12(15) . . . . ? C32 C27 C28 C29 1.3(3) . . . . ? C18 C27 C28 C29 -177.58(17) . . . . ? C27 C28 C29 C30 -0.1(3) . . . . ? C28 C29 C30 C31 -1.4(3) . . . . ? C29 C30 C31 C32 1.7(3) . . . . ? C30 C31 C32 C27 -0.6(3) . . . . ? C28 C27 C32 C31 -0.9(3) . . . . ? C18 C27 C32 C31 177.99(16) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.339 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.067 data_sl0027 _database_code_depnum_ccdc_archive 'CCDC 171366' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 Cl2 O9' _chemical_formula_weight 509.36 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' Cl Cl 0.1484 0.1585 '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 6.6987(3) _cell_length_b 13.8444(7) _cell_length_c 14.0583(7) _cell_angle_alpha 105.070(2) _cell_angle_beta 101.138(3) _cell_angle_gamma 95.648(3) _cell_volume 1219.91(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6249 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 1.024 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11124 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5545 _reflns_number_gt 3742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.5123P] 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 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5545 _refine_ls_number_parameters 302 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 -0.2965(2) 0.17725(13) 0.79406(12) 0.0359(4) Uani 1 1 d . . . O2 O -0.2478(2) 0.20947(11) 0.65482(11) 0.0279(3) Uani 1 1 d . . . O3 O 0.1444(2) 0.15534(10) 0.68455(10) 0.0228(3) Uani 1 1 d . . . O4 O 0.1380(2) 0.32699(11) 0.70282(11) 0.0288(4) Uani 1 1 d . . . O5 O -0.1553(2) 0.11262(12) 0.51369(11) 0.0321(4) Uani 1 1 d . . . O6 O 0.5044(2) -0.06961(12) 0.81700(11) 0.0332(4) Uani 1 1 d . . . O7 O 0.1812(2) -0.13570(11) 0.75626(12) 0.0351(4) Uani 1 1 d . . . O8 O 0.2215(2) 0.01696(11) 0.98532(11) 0.0285(3) Uani 1 1 d D . . H8 H 0.276(3) 0.0262(18) 1.0439(13) 0.034 Uiso 1 1 d D . . O9 O 0.2549(2) 0.49964(11) 1.09407(13) 0.0378(4) Uani 1 1 d . . . C1 C -0.1816(3) 0.18096(15) 0.73806(15) 0.0239(4) Uani 1 1 d . . . C2 C 0.0387(3) 0.16062(15) 0.76422(15) 0.0219(4) Uani 1 1 d . . . H2 H 0.1163 0.2175 0.8238 0.026 Uiso 1 1 calc R . . C3 C 0.1073(3) 0.23010(16) 0.63341(15) 0.0243(4) Uani 1 1 d . . . C4 C -0.1220(3) 0.21011(16) 0.58017(15) 0.0258(5) Uani 1 1 d . . . C5 C 0.2467(3) 0.21979(18) 0.55987(17) 0.0311(5) Uani 1 1 d . . . H5A H 0.2168 0.1507 0.5142 0.047 Uiso 1 1 calc R . . H5B H 0.3908 0.2339 0.5974 0.047 Uiso 1 1 calc R . . H5C H 0.2230 0.2681 0.5204 0.047 Uiso 1 1 calc R . . C6 C -0.1888(4) 0.2909(2) 0.53235(19) 0.0379(6) Uani 1 1 d . . . H6A H -0.1598 0.3566 0.5842 0.057 Uiso 1 1 calc R . . H6B H -0.3369 0.2743 0.5019 0.057 Uiso 1 1 calc R . . H6C H -0.1131 0.2944 0.4799 0.057 Uiso 1 1 calc R . . C7 C 0.3478(3) 0.36701(18) 0.75619(19) 0.0377(6) Uani 1 1 d . . . H7A H 0.3535 0.4344 0.8023 0.057 Uiso 1 1 calc R . . H7B H 0.4323 0.3721 0.7075 0.057 Uiso 1 1 calc R . . H7C H 0.4004 0.3218 0.7950 0.057 Uiso 1 1 calc R . . C8 C -0.3527(3) 0.0793(2) 0.44500(18) 0.0399(6) Uani 1 1 d . . . H8A H -0.3580 0.0103 0.4025 0.060 Uiso 1 1 calc R . . H8B H -0.3748 0.1247 0.4021 0.060 Uiso 1 1 calc R . . H8C H -0.4604 0.0802 0.4834 0.060 Uiso 1 1 calc R . . C9 C 0.0454(3) 0.06295(15) 0.79434(15) 0.0222(4) Uani 1 1 d . . . H9 H -0.0265 0.0682 0.8511 0.027 Uiso 1 1 calc R . . C10 C 0.2719(3) 0.05131(15) 0.83463(15) 0.0214(4) Uani 1 1 d . . . H10 H 0.3614 0.0959 0.8088 0.026 Uiso 1 1 calc R . . C11 C 0.3271(3) -0.05478(16) 0.80284(15) 0.0272(5) Uani 1 1 d . . . C12 C -0.0669(3) -0.02974(16) 0.70825(16) 0.0276(5) Uani 1 1 d . . . H12A H -0.2158 -0.0258 0.6917 0.033 Uiso 1 1 calc R . . H12B H -0.0128 -0.0319 0.6471 0.033 Uiso 1 1 calc R . . C13 C -0.0356(3) -0.12347(17) 0.73983(18) 0.0345(5) Uani 1 1 d . . . H13A H -0.0832 -0.1193 0.8030 0.041 Uiso 1 1 calc R . . H13B H -0.1187 -0.1833 0.6867 0.041 Uiso 1 1 calc R . . C14 C 0.3393(3) 0.08664(15) 0.95139(15) 0.0235(4) Uani 1 1 d . . . H14 H 0.4882 0.0810 0.9717 0.028 Uiso 1 1 calc R . . C15 C 0.3121(3) 0.19530(15) 0.99432(14) 0.0219(4) Uani 1 1 d . . . C16 C 0.4592(3) 0.27295(16) 0.99244(15) 0.0261(5) Uani 1 1 d . . . H16 H 0.5775 0.2566 0.9675 0.031 Uiso 1 1 calc R . . C17 C 0.4359(3) 0.37291(16) 1.02605(16) 0.0287(5) Uani 1 1 d . . . H17 H 0.5371 0.4248 1.0237 0.034 Uiso 1 1 calc R . . C18 C 0.2632(3) 0.39835(16) 1.06377(16) 0.0274(5) Uani 1 1 d . . . C19 C 0.1176(3) 0.32215(16) 1.06808(16) 0.0276(5) Uani 1 1 d . . . H19 H 0.0015 0.3385 1.0949 0.033 Uiso 1 1 calc R . . C20 C 0.1429(3) 0.22161(16) 1.03281(15) 0.0252(5) Uani 1 1 d . . . H20 H 0.0418 0.1696 1.0351 0.030 Uiso 1 1 calc R . . C21 C 0.0953(4) 0.53084(19) 1.1437(2) 0.0463(7) Uani 1 1 d . . . H21A H 0.1068 0.6048 1.1615 0.069 Uiso 1 1 calc R . . H21B H 0.1088 0.5091 1.2053 0.069 Uiso 1 1 calc R . . H21C H -0.0391 0.5001 1.0984 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.58056(14) 0.60469(7) 0.63873(7) 0.0745(3) Uani 1 1 d . . . Cl2 Cl 0.18255(14) 0.60123(7) 0.69321(8) 0.0823(3) Uani 1 1 d . . . C22 C 0.4341(4) 0.6639(2) 0.7201(2) 0.0522(7) Uani 1 1 d . . . H22A H 0.5021 0.6681 0.7905 0.063 Uiso 1 1 calc R . . H22B H 0.4305 0.7339 0.7157 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 0.0294(8) 0.0523(10) 0.0365(9) 0.0201(8) 0.0164(7) 0.0179(7) O2 0.0205(7) 0.0416(9) 0.0261(8) 0.0131(7) 0.0071(6) 0.0121(6) O3 0.0210(7) 0.0293(8) 0.0217(7) 0.0097(6) 0.0074(5) 0.0093(6) O4 0.0258(8) 0.0260(8) 0.0322(8) 0.0070(7) 0.0032(6) 0.0040(6) O5 0.0233(8) 0.0406(9) 0.0269(8) 0.0022(7) 0.0019(6) 0.0061(6) O6 0.0352(9) 0.0365(9) 0.0286(8) 0.0062(7) 0.0060(6) 0.0193(7) O7 0.0382(9) 0.0223(8) 0.0408(10) 0.0039(7) 0.0056(7) 0.0067(7) O8 0.0352(8) 0.0286(8) 0.0248(8) 0.0123(7) 0.0071(7) 0.0066(6) O9 0.0388(9) 0.0246(8) 0.0481(10) 0.0027(7) 0.0148(8) 0.0074(7) C1 0.0227(10) 0.0254(11) 0.0237(11) 0.0058(9) 0.0056(8) 0.0063(8) C2 0.0216(10) 0.0251(10) 0.0194(10) 0.0059(8) 0.0050(8) 0.0065(8) C3 0.0235(10) 0.0287(11) 0.0236(11) 0.0114(9) 0.0047(8) 0.0078(8) C4 0.0230(10) 0.0343(12) 0.0222(11) 0.0095(9) 0.0062(8) 0.0086(9) C5 0.0234(11) 0.0462(14) 0.0284(12) 0.0162(10) 0.0076(9) 0.0093(9) C6 0.0289(12) 0.0512(15) 0.0411(14) 0.0257(12) 0.0049(10) 0.0131(10) C7 0.0288(12) 0.0370(13) 0.0411(14) 0.0085(11) 0.0004(10) -0.0025(10) C8 0.0262(12) 0.0573(16) 0.0305(13) 0.0071(11) 0.0034(9) -0.0001(11) C9 0.0202(10) 0.0256(11) 0.0210(10) 0.0066(8) 0.0048(8) 0.0041(8) C10 0.0230(10) 0.0204(10) 0.0216(10) 0.0062(8) 0.0057(8) 0.0059(8) C11 0.0325(12) 0.0295(12) 0.0204(11) 0.0065(9) 0.0063(9) 0.0101(9) C12 0.0218(10) 0.0296(11) 0.0276(11) 0.0052(9) 0.0022(8) 0.0015(9) C13 0.0326(12) 0.0283(12) 0.0385(13) 0.0062(10) 0.0062(10) -0.0013(9) C14 0.0233(10) 0.0243(11) 0.0244(11) 0.0092(9) 0.0040(8) 0.0067(8) C15 0.0230(10) 0.0246(10) 0.0166(10) 0.0047(8) 0.0017(7) 0.0055(8) C16 0.0212(10) 0.0307(12) 0.0243(11) 0.0035(9) 0.0060(8) 0.0042(9) C17 0.0298(11) 0.0274(11) 0.0269(11) 0.0050(9) 0.0077(9) 0.0009(9) C18 0.0312(11) 0.0229(11) 0.0260(11) 0.0038(9) 0.0046(9) 0.0069(9) C19 0.0260(11) 0.0314(12) 0.0248(11) 0.0050(9) 0.0076(8) 0.0072(9) C20 0.0246(10) 0.0276(11) 0.0231(11) 0.0080(9) 0.0043(8) 0.0027(8) C21 0.0487(15) 0.0314(13) 0.0579(18) 0.0016(12) 0.0215(13) 0.0144(11) Cl1 0.0813(6) 0.0786(6) 0.0733(6) 0.0220(5) 0.0304(5) 0.0322(5) Cl2 0.0726(6) 0.0801(6) 0.1098(8) 0.0517(6) 0.0280(5) 0.0034(5) C22 0.0596(17) 0.0533(17) 0.0436(16) 0.0138(13) 0.0068(13) 0.0189(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.209(2) . ? O2 C1 1.340(2) . ? O2 C4 1.469(2) . ? O3 C3 1.421(2) . ? O3 C2 1.427(2) . ? O4 C3 1.408(2) . ? O4 C7 1.438(3) . ? O5 C4 1.396(3) . ? O5 C8 1.431(3) . ? O6 C11 1.213(3) . ? O7 C11 1.340(3) . ? O7 C13 1.459(3) . ? O8 C14 1.420(2) . ? O8 H8 0.805(16) . ? O9 C18 1.366(3) . ? O9 C21 1.428(3) . ? C1 C2 1.523(3) . ? C2 C9 1.521(3) . ? C2 H2 1.0000 . ? C3 C5 1.512(3) . ? C3 C4 1.536(3) . ? C4 C6 1.509(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C12 1.526(3) . ? C9 C10 1.553(3) . ? C9 H9 1.0000 . ? C10 C11 1.524(3) . ? C10 C14 1.546(3) . ? C10 H10 1.0000 . ? C12 C13 1.497(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.511(3) . ? C14 H14 1.0000 . ? C15 C20 1.388(3) . ? C15 C16 1.394(3) . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.401(3) . ? C17 H17 0.9500 . ? C18 C19 1.386(3) . ? C19 C20 1.390(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl1 C22 1.746(3) . ? Cl2 C22 1.741(3) . ? C22 H22A 0.9900 . ? C22 H22B 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 C1 O2 C4 121.79(15) . . ? C3 O3 C2 113.62(15) . . ? C3 O4 C7 115.49(16) . . ? C4 O5 C8 116.85(18) . . ? C11 O7 C13 119.78(17) . . ? C14 O8 H8 105.6(17) . . ? C18 O9 C21 117.67(17) . . ? O1 C1 O2 118.59(18) . . ? O1 C1 C2 121.18(19) . . ? O2 C1 C2 120.11(16) . . ? O3 C2 C9 108.34(15) . . ? O3 C2 C1 113.83(16) . . ? C9 C2 C1 111.20(16) . . ? O3 C2 H2 107.7 . . ? C9 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? O4 C3 O3 110.83(16) . . ? O4 C3 C5 114.03(17) . . ? O3 C3 C5 106.12(16) . . ? O4 C3 C4 104.99(16) . . ? O3 C3 C4 108.25(16) . . ? C5 C3 C4 112.57(17) . . ? O5 C4 O2 108.01(15) . . ? O5 C4 C6 115.01(18) . . ? O2 C4 C6 104.93(16) . . ? O5 C4 C3 105.31(16) . . ? O2 C4 C3 109.42(16) . . ? C6 C4 C3 114.01(18) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 C12 112.35(17) . . ? C2 C9 C10 110.24(15) . . ? C12 C9 C10 111.43(16) . . ? C2 C9 H9 107.5 . . ? C12 C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C11 C10 C14 105.56(16) . . ? C11 C10 C9 116.54(16) . . ? C14 C10 C9 112.97(15) . . ? C11 C10 H10 107.1 . . ? C14 C10 H10 107.1 . . ? C9 C10 H10 107.1 . . ? O6 C11 O7 117.1(2) . . ? O6 C11 C10 121.70(19) . . ? O7 C11 C10 121.22(18) . . ? C13 C12 C9 109.26(18) . . ? C13 C12 H12A 109.8 . . ? C9 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? C9 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? O7 C13 C12 110.91(17) . . ? O7 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? O7 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? O8 C14 C15 113.22(16) . . ? O8 C14 C10 105.73(15) . . ? C15 C14 C10 111.92(16) . . ? O8 C14 H14 108.6 . . ? C15 C14 H14 108.6 . . ? C10 C14 H14 108.6 . . ? C20 C15 C16 118.14(19) . . ? C20 C15 C14 122.84(17) . . ? C16 C15 C14 118.98(17) . . ? C17 C16 C15 121.07(18) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 120.18(19) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? O9 C18 C19 125.34(19) . . ? O9 C18 C17 115.18(18) . . ? C19 C18 C17 119.48(19) . . ? C18 C19 C20 119.48(19) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C15 C20 C19 121.63(19) . . ? C15 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? O9 C21 H21A 109.5 . . ? O9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Cl2 C22 Cl1 113.25(16) . . ? Cl2 C22 H22A 108.9 . . ? Cl1 C22 H22A 108.9 . . ? Cl2 C22 H22B 108.9 . . ? Cl1 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O2 C1 O1 -176.36(18) . . . . ? C4 O2 C1 C2 7.6(3) . . . . ? C3 O3 C2 C9 165.70(15) . . . . ? C3 O3 C2 C1 41.4(2) . . . . ? O1 C1 C2 O3 172.42(18) . . . . ? O2 C1 C2 O3 -11.6(3) . . . . ? O1 C1 C2 C9 49.7(3) . . . . ? O2 C1 C2 C9 -134.35(18) . . . . ? C7 O4 C3 O3 68.7(2) . . . . ? C7 O4 C3 C5 -50.9(2) . . . . ? C7 O4 C3 C4 -174.59(17) . . . . ? C2 O3 C3 O4 50.1(2) . . . . ? C2 O3 C3 C5 174.40(15) . . . . ? C2 O3 C3 C4 -64.5(2) . . . . ? C8 O5 C4 O2 70.6(2) . . . . ? C8 O5 C4 C6 -46.2(2) . . . . ? C8 O5 C4 C3 -172.60(17) . . . . ? C1 O2 C4 O5 84.7(2) . . . . ? C1 O2 C4 C6 -152.18(18) . . . . ? C1 O2 C4 C3 -29.5(2) . . . . ? O4 C3 C4 O5 -177.97(15) . . . . ? O3 C3 C4 O5 -59.56(19) . . . . ? C5 C3 C4 O5 57.4(2) . . . . ? O4 C3 C4 O2 -62.1(2) . . . . ? O3 C3 C4 O2 56.3(2) . . . . ? C5 C3 C4 O2 173.30(17) . . . . ? O4 C3 C4 C6 55.0(2) . . . . ? O3 C3 C4 C6 173.44(17) . . . . ? C5 C3 C4 C6 -69.6(2) . . . . ? O3 C2 C9 C12 -63.0(2) . . . . ? C1 C2 C9 C12 62.8(2) . . . . ? O3 C2 C9 C10 61.91(19) . . . . ? C1 C2 C9 C10 -172.28(15) . . . . ? C2 C9 C10 C11 -139.96(17) . . . . ? C12 C9 C10 C11 -14.5(2) . . . . ? C2 C9 C10 C14 97.54(19) . . . . ? C12 C9 C10 C14 -137.00(17) . . . . ? C13 O7 C11 O6 178.06(19) . . . . ? C13 O7 C11 C10 -3.1(3) . . . . ? C14 C10 C11 O6 -65.1(2) . . . . ? C9 C10 C11 O6 168.64(19) . . . . ? C14 C10 C11 O7 116.1(2) . . . . ? C9 C10 C11 O7 -10.2(3) . . . . ? C2 C9 C12 C13 174.28(16) . . . . ? C10 C9 C12 C13 50.0(2) . . . . ? C11 O7 C13 C12 40.8(3) . . . . ? C9 C12 C13 O7 -64.4(2) . . . . ? C11 C10 C14 O8 -61.49(19) . . . . ? C9 C10 C14 O8 67.0(2) . . . . ? C11 C10 C14 C15 174.81(16) . . . . ? C9 C10 C14 C15 -56.7(2) . . . . ? O8 C14 C15 C20 -20.9(3) . . . . ? C10 C14 C15 C20 98.5(2) . . . . ? O8 C14 C15 C16 161.27(18) . . . . ? C10 C14 C15 C16 -79.4(2) . . . . ? C20 C15 C16 C17 -1.1(3) . . . . ? C14 C15 C16 C17 176.76(19) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C21 O9 C18 C19 6.8(3) . . . . ? C21 O9 C18 C17 -173.0(2) . . . . ? C16 C17 C18 O9 -179.4(2) . . . . ? C16 C17 C18 C19 0.8(3) . . . . ? O9 C18 C19 C20 178.8(2) . . . . ? C17 C18 C19 C20 -1.4(3) . . . . ? C16 C15 C20 C19 0.5(3) . . . . ? C14 C15 C20 C19 -177.34(19) . . . . ? C18 C19 C20 C15 0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.701 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.066 data_sl0028 _database_code_depnum_ccdc_archive 'CCDC 171367' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H29 N O9' _chemical_formula_weight 463.47 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.6048(6) _cell_length_b 7.9540(4) _cell_length_c 19.9249(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.051(3) _cell_angle_gamma 90.00 _cell_volume 2285.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6757 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method ? _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multiscan _exptl_absorpt_process_details 'Sortav Blessing (1995) ' _exptl_absorpt_correction_T_max 1.056 _exptl_absorpt_correction_T_min 0.944 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11649 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5167 _reflns_number_observed 2951 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 12 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1696P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5155 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_obs 0.0524 _refine_ls_wR_factor_all 0.1746 _refine_ls_wR_factor_obs 0.1080 _refine_ls_goodness_of_fit_all 1.012 _refine_ls_goodness_of_fit_obs 1.140 _refine_ls_restrained_S_all 1.365 _refine_ls_restrained_S_obs 1.140 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.08550(9) -0.1703(2) 0.56427(7) 0.0441(4) Uani 1 d . . O2 O 0.18893(8) -0.02783(15) 0.63370(6) 0.0364(3) Uani 1 d . . O3 O 0.19068(9) 0.22533(15) 0.53587(6) 0.0372(3) Uani 1 d . . O4 O 0.12584(10) 0.2950(2) 0.63174(6) 0.0453(4) Uani 1 d . . O5 O 0.33165(9) 0.0761(2) 0.61708(7) 0.0467(4) Uani 1 d . . O6 O 0.20680(12) 0.4209(2) 0.39648(7) 0.0622(5) Uani 1 d . . O7 O 0.30093(10) 0.2072(2) 0.42322(7) 0.0521(4) Uani 1 d . . O8 O 0.02767(12) 0.3612(2) 0.27822(8) 0.0626(5) Uani 1 d . . O9 O 0.13874(12) 0.4605(2) 0.23043(8) 0.0680(5) Uani 1 d . . N1 N 0.10287(13) 0.3480(2) 0.25930(8) 0.0445(4) Uani 1 d . . C1 C 0.13365(13) -0.0472(2) 0.57361(9) 0.0334(4) Uani 1 d . . C2 C 0.12848(13) 0.0884(2) 0.52004(9) 0.0336(4) Uani 1 d . . H2 H 0.06403(13) 0.1348(2) 0.51302(9) 0.040 Uiso 1 calc R . C3 C 0.20902(14) 0.2679(2) 0.60603(9) 0.0380(5) Uani 1 d . . C4 C 0.25305(13) 0.1150(2) 0.64519(9) 0.0364(5) Uani 1 d . . C5 C 0.2731(2) 0.4179(3) 0.61057(10) 0.0555(6) Uani 1 d . . H5A H 0.2419(4) 0.5109(6) 0.5839(6) 0.083 Uiso 1 calc R . H5B H 0.3296(5) 0.3876(6) 0.5926(7) 0.083 Uiso 1 calc R . H5C H 0.2893(8) 0.4525(12) 0.65815(13) 0.083 Uiso 1 calc R . C6 C 0.2703(2) 0.1368(3) 0.72163(9) 0.0495(6) Uani 1 d . . H6A H 0.2891(9) 0.0290(4) 0.74330(9) 0.074 Uiso 1 calc R . H6B H 0.2133(3) 0.1758(15) 0.73689(12) 0.074 Uiso 1 calc R . H6C H 0.3196(6) 0.2198(12) 0.73419(10) 0.074 Uiso 1 calc R . C7 C 0.0692(2) 0.4328(3) 0.60264(12) 0.0682(7) Uani 1 d . . H7A H 0.0994(6) 0.5394(3) 0.6175(7) 0.102 Uiso 1 calc R . H7B H 0.0084(4) 0.4273(12) 0.6176(7) 0.102 Uiso 1 calc R . H7C H 0.0610(10) 0.4257(12) 0.55296(12) 0.102 Uiso 1 calc R . C8 C 0.38325(15) -0.0684(3) 0.64482(11) 0.0560(6) Uani 1 d . . H8A H 0.4172(8) -0.0410(6) 0.6899(3) 0.084 Uiso 1 calc R . H8B H 0.4273(7) -0.1013(11) 0.6148(4) 0.084 Uiso 1 calc R . H8C H 0.3405(2) -0.1617(6) 0.6487(7) 0.084 Uiso 1 calc R . C9 C 0.14638(13) 0.0148(2) 0.45177(8) 0.0328(4) Uani 1 d . . H9 H 0.09946(13) -0.0754(2) 0.43811(8) 0.039 Uiso 1 calc R . C10 C 0.13436(13) 0.1502(2) 0.39564(8) 0.0342(4) Uani 1 d . . H10 H 0.07582(13) 0.2133(2) 0.39831(8) 0.041 Uiso 1 calc R . C11 C 0.2134(2) 0.2725(3) 0.40641(9) 0.0451(5) Uani 1 d . . C12 C 0.24140(13) -0.0621(2) 0.45570(8) 0.0352(5) Uani 1 d . . C13 C 0.31321(14) 0.0374(3) 0.44070(9) 0.0435(5) Uani 1 d . . C14 C 0.4014(2) -0.0262(4) 0.44238(11) 0.0572(7) Uani 1 d . . H14 H 0.4497(2) 0.0440(4) 0.43156(11) 0.069 Uiso 1 calc R . C15 C 0.4190(2) -0.1917(4) 0.45981(11) 0.0622(7) Uani 1 d . . H15 H 0.4799(2) -0.2355(4) 0.46156(11) 0.075 Uiso 1 calc R . C16 C 0.3490(2) -0.2946(3) 0.47475(10) 0.0512(6) Uani 1 d . . H16 H 0.3613(2) -0.4088(3) 0.48690(10) 0.061 Uiso 1 calc R . C17 C 0.26058(14) -0.2299(3) 0.47188(9) 0.0408(5) Uani 1 d . . H17 H 0.21199(14) -0.3014(3) 0.48113(9) 0.049 Uiso 1 calc R . C18 C 0.12608(13) 0.0695(2) 0.32376(9) 0.0355(4) Uani 1 d . . H18 H 0.17153(13) -0.0254(2) 0.32873(9) 0.043 Uiso 1 calc R . C19 C 0.15512(13) 0.1840(2) 0.26899(9) 0.0364(5) Uani 1 d . . H19 H 0.22238(13) 0.2109(2) 0.28252(9) 0.044 Uiso 1 calc R . C20 C 0.14353(15) 0.0962(3) 0.19992(10) 0.0489(5) Uani 1 d . . H20A H 0.15669(15) 0.1775(3) 0.16503(10) 0.059 Uiso 1 calc R . H20B H 0.18925(15) 0.0038(3) 0.20176(10) 0.059 Uiso 1 calc R . C21 C 0.0470(2) 0.0254(3) 0.17930(10) 0.0557(6) Uani 1 d . . H21A H 0.0436(2) -0.0339(3) 0.13530(10) 0.067 Uiso 1 calc R . H21B H 0.0015(2) 0.1186(3) 0.17332(10) 0.067 Uiso 1 calc R . C22 C 0.0229(2) -0.0957(3) 0.23278(10) 0.0596(6) Uani 1 d . . H22A H 0.0652(2) -0.1936(3) 0.23574(10) 0.072 Uiso 1 calc R . H22B H -0.0412(2) -0.1371(3) 0.21901(10) 0.072 Uiso 1 calc R . C23 C 0.03092(15) -0.0123(3) 0.30250(10) 0.0493(6) Uani 1 d . . H23A H 0.02068(15) -0.0977(3) 0.33669(10) 0.059 Uiso 1 calc R . H23B H -0.01795(15) 0.0744(3) 0.30133(10) 0.059 Uiso 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 0.0463(9) 0.0432(8) 0.0434(8) 0.0072(6) 0.0085(6) -0.0147(7) O2 0.0396(8) 0.0408(8) 0.0285(7) 0.0084(6) 0.0049(6) -0.0019(6) O3 0.0520(8) 0.0369(7) 0.0226(6) 0.0031(5) 0.0059(6) -0.0128(6) O4 0.0611(10) 0.0418(8) 0.0355(8) 0.0067(6) 0.0157(7) 0.0109(7) O5 0.0404(8) 0.0625(9) 0.0388(8) 0.0048(7) 0.0109(6) -0.0016(7) O6 0.1039(13) 0.0421(9) 0.0402(9) 0.0028(7) 0.0102(8) -0.0288(9) O7 0.0557(10) 0.0616(10) 0.0400(8) -0.0027(7) 0.0103(7) -0.0307(8) O8 0.0590(11) 0.0702(11) 0.0613(10) 0.0077(8) 0.0175(9) 0.0202(8) O9 0.0855(13) 0.0564(10) 0.0608(11) 0.0246(8) 0.0070(9) -0.0113(9) N1 0.0525(12) 0.0493(11) 0.0303(9) 0.0052(8) 0.0023(8) -0.0002(9) C1 0.0335(11) 0.0398(11) 0.0282(10) 0.0039(9) 0.0095(8) 0.0028(9) C2 0.0346(11) 0.0372(11) 0.0288(10) 0.0053(8) 0.0048(8) -0.0048(9) C3 0.0522(13) 0.0403(11) 0.0222(9) 0.0005(8) 0.0079(9) -0.0076(10) C4 0.0383(12) 0.0440(12) 0.0276(10) 0.0011(9) 0.0072(9) -0.0058(9) C5 0.084(2) 0.0512(13) 0.0304(11) -0.0020(10) 0.0077(11) -0.0237(12) C6 0.0653(15) 0.0569(14) 0.0259(10) 0.0017(10) 0.0056(10) -0.0016(11) C7 0.094(2) 0.0556(15) 0.058(2) 0.0139(12) 0.0193(14) 0.0308(14) C8 0.0414(13) 0.073(2) 0.0523(14) -0.0015(12) 0.0021(10) 0.0111(12) C9 0.0361(11) 0.0378(10) 0.0239(9) 0.0014(8) 0.0032(8) -0.0089(9) C10 0.0406(11) 0.0368(10) 0.0252(9) 0.0004(8) 0.0054(8) -0.0091(9) C11 0.063(2) 0.0500(14) 0.0225(10) -0.0004(10) 0.0072(10) -0.0193(12) C12 0.0357(11) 0.0477(12) 0.0216(9) -0.0051(9) 0.0028(8) -0.0077(9) C13 0.0395(12) 0.0645(15) 0.0262(10) -0.0099(10) 0.0044(8) -0.0170(11) C14 0.0379(13) 0.097(2) 0.0376(12) -0.0212(13) 0.0069(10) -0.0212(13) C15 0.0385(14) 0.105(2) 0.0417(13) -0.0302(14) 0.0011(10) 0.0085(14) C16 0.0486(14) 0.0657(15) 0.0372(12) -0.0153(11) -0.0001(10) 0.0111(12) C17 0.0423(13) 0.0509(13) 0.0279(10) -0.0036(9) 0.0020(9) -0.0017(10) C18 0.0426(11) 0.0389(10) 0.0242(9) 0.0004(8) 0.0029(8) -0.0038(9) C19 0.0359(11) 0.0440(11) 0.0287(10) 0.0032(9) 0.0036(8) 0.0037(9) C20 0.0522(14) 0.0649(14) 0.0299(11) -0.0003(10) 0.0072(10) 0.0097(11) C21 0.069(2) 0.0662(15) 0.0287(11) -0.0098(11) -0.0034(11) -0.0023(12) C22 0.074(2) 0.0609(15) 0.0397(13) -0.0113(11) -0.0030(11) -0.0210(13) C23 0.0563(14) 0.0555(13) 0.0351(11) -0.0022(10) 0.0041(10) -0.0219(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.203(2) . ? O2 C1 1.343(2) . ? O2 C4 1.467(2) . ? O3 C2 1.421(2) . ? O3 C3 1.422(2) . ? O4 C3 1.407(2) . ? O4 C7 1.440(2) . ? O5 C4 1.389(2) . ? O5 C8 1.436(2) . ? O6 C11 1.199(2) . ? O7 C11 1.371(3) . ? O7 C13 1.399(3) . ? O8 N1 1.220(2) . ? O9 N1 1.225(2) . ? N1 C19 1.508(3) . ? C1 C2 1.511(3) . ? C2 C9 1.540(2) . ? C2 H2 1.00 . ? C3 C5 1.510(3) . ? C3 C4 1.531(3) . ? C4 C6 1.514(2) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 C12 1.507(3) . ? C9 C10 1.542(2) . ? C9 H9 1.00 . ? C10 C11 1.499(3) . ? C10 C18 1.557(2) . ? C10 H10 1.00 . ? C12 C13 1.384(3) . ? C12 C17 1.391(3) . ? C13 C14 1.379(3) . ? C14 C15 1.376(3) . ? C14 H14 0.95 . ? C15 C16 1.379(3) . ? C15 H15 0.95 . ? C16 C17 1.383(3) . ? C16 H16 0.95 . ? C17 H17 0.95 . ? C18 C19 1.532(3) . ? C18 C23 1.533(3) . ? C18 H18 1.00 . ? C19 C20 1.529(3) . ? C19 H19 1.00 . ? C20 C21 1.513(3) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C22 1.518(3) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.527(3) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 120.48(13) . . ? C2 O3 C3 114.56(13) . . ? C3 O4 C7 116.4(2) . . ? C4 O5 C8 116.10(15) . . ? C11 O7 C13 120.3(2) . . ? O8 N1 O9 123.7(2) . . ? O8 N1 C19 119.8(2) . . ? O9 N1 C19 116.5(2) . . ? O1 C1 O2 119.1(2) . . ? O1 C1 C2 120.6(2) . . ? O2 C1 C2 120.3(2) . . ? O3 C2 C1 115.53(15) . . ? O3 C2 C9 107.20(14) . . ? C1 C2 C9 110.86(15) . . ? O3 C2 H2 107.65(9) . . ? C1 C2 H2 107.65(10) . . ? C9 C2 H2 107.65(10) . . ? O4 C3 O3 110.75(15) . . ? O4 C3 C5 114.8(2) . . ? O3 C3 C5 105.43(14) . . ? O4 C3 C4 104.67(14) . . ? O3 C3 C4 108.10(15) . . ? C5 C3 C4 113.0(2) . . ? O5 C4 O2 108.20(14) . . ? O5 C4 C6 114.4(2) . . ? O2 C4 C6 104.30(14) . . ? O5 C4 C3 106.20(14) . . ? O2 C4 C3 109.21(14) . . ? C6 C4 C3 114.3(2) . . ? C3 C5 H5A 109.47(11) . . ? C3 C5 H5B 109.47(12) . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.47(10) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.47(11) . . ? C4 C6 H6B 109.47(11) . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.47(11) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.47(12) . . ? O4 C7 H7B 109.47(12) . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.47(11) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.47(10) . . ? O5 C8 H8B 109.47(10) . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.47(10) . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C9 C2 113.02(14) . . ? C12 C9 C10 108.66(15) . . ? C2 C9 C10 111.06(14) . . ? C12 C9 H9 107.98(10) . . ? C2 C9 H9 107.98(9) . . ? C10 C9 H9 107.98(9) . . ? C11 C10 C9 110.6(2) . . ? C11 C10 C18 110.23(14) . . ? C9 C10 C18 111.28(14) . . ? C11 C10 H10 108.20(12) . . ? C9 C10 H10 108.20(10) . . ? C18 C10 H10 108.20(10) . . ? O6 C11 O7 117.5(2) . . ? O6 C11 C10 125.1(2) . . ? O7 C11 C10 117.1(2) . . ? C13 C12 C17 117.8(2) . . ? C13 C12 C9 118.6(2) . . ? C17 C12 C9 123.5(2) . . ? C14 C13 C12 121.5(2) . . ? C14 C13 O7 116.3(2) . . ? C12 C13 O7 122.3(2) . . ? C15 C14 C13 119.6(2) . . ? C15 C14 H14 120.20(14) . . ? C13 C14 H14 120.20(15) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.76(14) . . ? C16 C15 H15 119.76(14) . . ? C15 C16 C17 119.3(2) . . ? C15 C16 H16 120.34(15) . . ? C17 C16 H16 120.34(14) . . ? C16 C17 C12 121.3(2) . . ? C16 C17 H17 119.35(14) . . ? C12 C17 H17 119.35(11) . . ? C19 C18 C23 113.3(2) . . ? C19 C18 C10 114.86(15) . . ? C23 C18 C10 111.4(2) . . ? C19 C18 H18 105.41(10) . . ? C23 C18 H18 105.41(12) . . ? C10 C18 H18 105.41(10) . . ? N1 C19 C20 107.32(15) . . ? N1 C19 C18 114.46(15) . . ? C20 C19 C18 111.5(2) . . ? N1 C19 H19 107.78(10) . . ? C20 C19 H19 107.78(11) . . ? C18 C19 H19 107.78(10) . . ? C21 C20 C19 112.4(2) . . ? C21 C20 H20A 109.12(11) . . ? C19 C20 H20A 109.12(11) . . ? C21 C20 H20B 109.12(12) . . ? C19 C20 H20B 109.12(10) . . ? H20A C20 H20B 107.9 . . ? C20 C21 C22 110.7(2) . . ? C20 C21 H21A 109.49(11) . . ? C22 C21 H21A 109.49(11) . . ? C20 C21 H21B 109.49(12) . . ? C22 C21 H21B 109.49(13) . . ? H21A C21 H21B 108.1 . . ? C21 C22 C23 111.7(2) . . ? C21 C22 H22A 109.28(13) . . ? C23 C22 H22A 109.28(13) . . ? C21 C22 H22B 109.28(12) . . ? C23 C22 H22B 109.28(12) . . ? H22A C22 H22B 107.9 . . ? C22 C23 C18 111.8(2) . . ? C22 C23 H23A 109.25(12) . . ? C18 C23 H23A 109.25(10) . . ? C22 C23 H23B 109.25(13) . . ? C18 C23 H23B 109.25(12) . . ? H23A C23 H23B 107.9 . . ? 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 C4 O2 C1 O1 175.9(2) . . . . ? C4 O2 C1 C2 -7.3(2) . . . . ? C3 O3 C2 C1 -33.5(2) . . . . ? C3 O3 C2 C9 -157.65(14) . . . . ? O1 C1 C2 O3 -178.1(2) . . . . ? O2 C1 C2 O3 5.1(2) . . . . ? O1 C1 C2 C9 -55.9(2) . . . . ? O2 C1 C2 C9 127.3(2) . . . . ? C7 O4 C3 O3 -63.1(2) . . . . ? C7 O4 C3 C5 56.2(2) . . . . ? C7 O4 C3 C4 -179.3(2) . . . . ? C2 O3 C3 O4 -53.4(2) . . . . ? C2 O3 C3 C5 -178.1(2) . . . . ? C2 O3 C3 C4 60.8(2) . . . . ? C8 O5 C4 O2 -61.0(2) . . . . ? C8 O5 C4 C6 54.8(2) . . . . ? C8 O5 C4 C3 -178.1(2) . . . . ? C1 O2 C4 O5 -81.3(2) . . . . ? C1 O2 C4 C6 156.5(2) . . . . ? C1 O2 C4 C3 33.9(2) . . . . ? O4 C3 C4 O5 175.16(13) . . . . ? O3 C3 C4 O5 57.1(2) . . . . ? C5 C3 C4 O5 -59.2(2) . . . . ? O4 C3 C4 O2 58.7(2) . . . . ? O3 C3 C4 O2 -59.4(2) . . . . ? C5 C3 C4 O2 -175.68(14) . . . . ? O4 C3 C4 C6 -57.7(2) . . . . ? O3 C3 C4 C6 -175.8(2) . . . . ? C5 C3 C4 C6 67.9(2) . . . . ? O3 C2 C9 C12 65.3(2) . . . . ? C1 C2 C9 C12 -61.6(2) . . . . ? O3 C2 C9 C10 -57.1(2) . . . . ? C1 C2 C9 C10 175.99(15) . . . . ? C12 C9 C10 C11 -52.6(2) . . . . ? C2 C9 C10 C11 72.3(2) . . . . ? C12 C9 C10 C18 70.3(2) . . . . ? C2 C9 C10 C18 -164.82(15) . . . . ? C13 O7 C11 O6 174.9(2) . . . . ? C13 O7 C11 C10 -10.6(2) . . . . ? C9 C10 C11 O6 -141.8(2) . . . . ? C18 C10 C11 O6 94.7(2) . . . . ? C9 C10 C11 O7 44.2(2) . . . . ? C18 C10 C11 O7 -79.3(2) . . . . ? C2 C9 C12 C13 -91.8(2) . . . . ? C10 C9 C12 C13 31.9(2) . . . . ? C2 C9 C12 C17 90.0(2) . . . . ? C10 C9 C12 C17 -146.2(2) . . . . ? C17 C12 C13 C14 -0.8(3) . . . . ? C9 C12 C13 C14 -179.0(2) . . . . ? C17 C12 C13 O7 179.4(2) . . . . ? C9 C12 C13 O7 1.1(3) . . . . ? C11 O7 C13 C14 166.4(2) . . . . ? C11 O7 C13 C12 -13.8(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? O7 C13 C14 C15 179.4(2) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C12 -1.5(3) . . . . ? C13 C12 C17 C16 1.7(3) . . . . ? C9 C12 C17 C16 179.9(2) . . . . ? C11 C10 C18 C19 -31.9(2) . . . . ? C9 C10 C18 C19 -155.0(2) . . . . ? C11 C10 C18 C23 -162.5(2) . . . . ? C9 C10 C18 C23 74.4(2) . . . . ? O8 N1 C19 C20 103.4(2) . . . . ? O9 N1 C19 C20 -74.6(2) . . . . ? O8 N1 C19 C18 -20.9(2) . . . . ? O9 N1 C19 C18 161.2(2) . . . . ? C23 C18 C19 N1 72.5(2) . . . . ? C10 C18 C19 N1 -57.1(2) . . . . ? C23 C18 C19 C20 -49.5(2) . . . . ? C10 C18 C19 C20 -179.2(2) . . . . ? N1 C19 C20 C21 -73.1(2) . . . . ? C18 C19 C20 C21 53.0(2) . . . . ? C19 C20 C21 C22 -56.9(2) . . . . ? C20 C21 C22 C23 56.9(3) . . . . ? C21 C22 C23 C18 -53.5(3) . . . . ? C19 C18 C23 C22 50.1(2) . . . . ? C10 C18 C23 C22 -178.6(2) . . . . ? _refine_diff_density_max 0.204 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.053 data_sl0105 _database_code_depnum_ccdc_archive 'CCDC 171368' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H30 O10' _chemical_formula_weight 442.45 _chemical_melting_point ? _chemical_compound_source ? 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)/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 10.4467(3) _cell_length_b 11.4334(4) _cell_length_c 18.6140(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.264(2) _cell_angle_gamma 90.00 _cell_volume 2222.74(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 15579 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multiscan _exptl_absorpt_process_details 'Sortav Blessing (1995) ' _exptl_absorpt_correction_T_max 1.214 _exptl_absorpt_correction_T_min 0.904 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19327 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5064 _reflns_number_observed 3463 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.3152P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0087(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5054 _refine_ls_number_parameters 296 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_obs 0.0497 _refine_ls_wR_factor_all 0.1639 _refine_ls_wR_factor_obs 0.1135 _refine_ls_goodness_of_fit_all 1.049 _refine_ls_goodness_of_fit_obs 1.116 _refine_ls_restrained_S_all 1.316 _refine_ls_restrained_S_obs 1.116 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.63232(14) 0.32386(13) 1.01451(7) 0.0520(4) Uani 1 d . . O2 O 0.78108(11) 0.40519(10) 0.95120(6) 0.0342(3) Uani 1 d . . O3 O 0.66595(9) 0.32072(9) 0.82249(5) 0.0276(3) Uani 1 d . . O4 O 0.86798(10) 0.24920(9) 0.85255(6) 0.0333(3) Uani 1 d . . O5 O 0.74012(11) 0.53458(10) 0.85813(6) 0.0351(3) Uani 1 d . . O6 O 0.23700(13) 0.23704(13) 0.73789(7) 0.0505(4) Uani 1 d . . O7 O 0.24479(12) 0.39404(12) 0.80410(7) 0.0483(4) Uani 1 d . . O8 O 0.48471(11) 0.05124(11) 0.86699(7) 0.0413(3) Uani 1 d D . H8 H 0.4706(20) -0.0319(18) 0.8711(11) 0.062 Uiso 1 d D . O9 O 0.04805(11) 0.11789(11) 1.09647(6) 0.0426(3) Uani 1 d . . O10 O 0.56163(14) 0.18318(12) 1.13206(8) 0.0452(3) Uani 1 d D . H10B H 0.6156(22) 0.2092(21) 1.1665(12) 0.068 Uiso 1 d D . H10A H 0.5809(21) 0.2184(20) 1.0921(11) 0.068 Uiso 1 d D . C1 C 0.6743(2) 0.34153(15) 0.95553(9) 0.0324(4) Uani 1 d . . C2 C 0.61327(14) 0.28621(14) 0.88946(8) 0.0287(4) Uani 1 d . . H2 H 0.62406(14) 0.19959(14) 0.89395(8) 0.034 Uiso 1 calc R . C3 C 0.79851(14) 0.34576(13) 0.82548(8) 0.0272(4) Uani 1 d . . C4 C 0.82135(15) 0.44456(14) 0.88002(9) 0.0305(4) Uani 1 d . . C5 C 0.8347(2) 0.3807(2) 0.75053(9) 0.0389(4) Uani 1 d . . H5A H 0.8046(10) 0.3211(5) 0.71632(12) 0.058 Uiso 1 calc R . H5B H 0.9280(2) 0.3878(10) 0.7482(2) 0.058 Uiso 1 calc R . H5C H 0.7950(9) 0.4561(5) 0.7384(3) 0.058 Uiso 1 calc R . C6 C 0.9601(2) 0.4785(2) 0.89086(11) 0.0468(5) Uani 1 d . . H6A H 0.9683(2) 0.5327(9) 0.9315(5) 0.070 Uiso 1 calc R . H6B H 0.9907(4) 0.5164(11) 0.8473(3) 0.070 Uiso 1 calc R . H6C H 1.0113(3) 0.4083(2) 0.9009(7) 0.070 Uiso 1 calc R . C7 C 0.8628(2) 0.1474(2) 0.80772(12) 0.0489(5) Uani 1 d . . H7A H 0.8911(12) 0.0790(3) 0.8355(2) 0.073 Uiso 1 calc R . H7B H 0.9190(10) 0.1583(5) 0.7668(4) 0.073 Uiso 1 calc R . H7C H 0.7747(3) 0.1352(7) 0.7902(6) 0.073 Uiso 1 calc R . C8 C 0.7461(2) 0.6407(2) 0.89878(12) 0.0517(5) Uani 1 d . . H8B H 0.6702(7) 0.6882(6) 0.8877(6) 0.078 Uiso 1 calc R . H8C H 0.8232(7) 0.6843(6) 0.8863(6) 0.078 Uiso 1 calc R . H8D H 0.7490(14) 0.6221(2) 0.95019(12) 0.078 Uiso 1 calc R . C9 C 0.46941(15) 0.31163(14) 0.88468(9) 0.0319(4) Uani 1 d . . H9 H 0.43199(15) 0.29029(14) 0.93190(9) 0.038 Uiso 1 calc R . C10 C 0.40445(15) 0.23490(15) 0.82645(9) 0.0322(4) Uani 1 d . . H10 H 0.47047(15) 0.22281(15) 0.78907(9) 0.039 Uiso 1 calc R . C11 C 0.2898(2) 0.2887(2) 0.78703(9) 0.0381(4) Uani 1 d . . C12 C 0.4417(2) 0.4406(2) 0.87119(11) 0.0428(5) Uani 1 d . . H12A H 0.4770(2) 0.4879(2) 0.91157(11) 0.051 Uiso 1 calc R . H12B H 0.4836(2) 0.4661(2) 0.82662(11) 0.051 Uiso 1 calc R . C13 C 0.2997(2) 0.4599(2) 0.86413(12) 0.0511(5) Uani 1 d . . H13A H 0.2585(2) 0.4354(2) 0.90909(12) 0.061 Uiso 1 calc R . H13B H 0.2824(2) 0.5442(2) 0.85688(12) 0.061 Uiso 1 calc R . C14 C 0.36809(14) 0.11073(15) 0.85248(9) 0.0322(4) Uani 1 d . . H14 H 0.32201(14) 0.06951(15) 0.81220(9) 0.039 Uiso 1 calc R . C15 C 0.28108(14) 0.11279(14) 0.91729(9) 0.0284(4) Uani 1 d . . C16 C 0.15463(15) 0.14873(15) 0.91009(9) 0.0331(4) Uani 1 d . . H16 H 0.12251(15) 0.17166(15) 0.86407(9) 0.040 Uiso 1 calc R . C17 C 0.07353(15) 0.15218(15) 0.96828(9) 0.0330(4) Uani 1 d . . H17 H -0.01236(15) 0.17822(15) 0.96210(9) 0.040 Uiso 1 calc R . C18 C 0.11905(15) 0.11736(14) 1.03517(9) 0.0306(4) Uani 1 d . . C19 C 0.2447(2) 0.0804(2) 1.04359(9) 0.0357(4) Uani 1 d . . H19 H 0.2760(2) 0.0558(2) 1.08944(9) 0.043 Uiso 1 calc R . C20 C 0.3248(2) 0.07944(15) 0.98533(9) 0.0328(4) Uani 1 d . . H20 H 0.4114(2) 0.05550(15) 0.99198(9) 0.039 Uiso 1 calc R . C21 C -0.0811(2) 0.1577(2) 1.09005(11) 0.0502(5) Uani 1 d . . H21A H -0.1219(5) 0.1519(12) 1.1368(2) 0.075 Uiso 1 calc R . H21B H -0.1280(4) 0.1092(8) 1.0549(6) 0.075 Uiso 1 calc R . H21C H -0.0822(2) 0.2393(4) 1.0740(7) 0.075 Uiso 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 0.0639(9) 0.0643(9) 0.0280(7) 0.0070(6) 0.0062(6) -0.0170(7) O2 0.0396(7) 0.0362(7) 0.0267(6) -0.0006(5) -0.0021(5) -0.0097(5) O3 0.0247(5) 0.0343(6) 0.0238(6) 0.0006(5) 0.0009(4) -0.0029(4) O4 0.0324(6) 0.0269(6) 0.0402(7) -0.0003(5) -0.0058(5) 0.0027(5) O5 0.0425(7) 0.0248(6) 0.0381(7) -0.0014(5) 0.0020(5) 0.0023(5) O6 0.0538(8) 0.0605(9) 0.0367(7) 0.0038(7) -0.0124(6) -0.0066(7) O7 0.0394(7) 0.0508(8) 0.0546(8) 0.0018(7) -0.0053(6) 0.0042(6) O8 0.0289(6) 0.0351(7) 0.0601(8) -0.0076(6) 0.0059(6) 0.0018(5) O9 0.0423(7) 0.0476(8) 0.0382(7) -0.0031(6) 0.0109(5) -0.0036(6) O10 0.0550(8) 0.0438(8) 0.0368(8) 0.0074(6) 0.0005(6) -0.0121(6) C1 0.0382(9) 0.0324(9) 0.0265(9) 0.0052(7) 0.0007(7) -0.0035(7) C2 0.0314(8) 0.0280(8) 0.0268(8) 0.0024(7) 0.0029(6) -0.0055(7) C3 0.0240(8) 0.0272(8) 0.0304(9) 0.0027(7) 0.0009(6) -0.0002(6) C4 0.0311(8) 0.0291(9) 0.0313(9) 0.0026(7) 0.0026(7) -0.0036(7) C5 0.0442(10) 0.0383(10) 0.0347(10) 0.0026(8) 0.0135(8) 0.0038(8) C6 0.0361(10) 0.0444(11) 0.0598(13) -0.0044(10) 0.0001(9) -0.0104(8) C7 0.0547(12) 0.0301(10) 0.0613(13) -0.0079(9) -0.0111(10) 0.0056(9) C8 0.0695(14) 0.0314(10) 0.0543(13) -0.0086(9) 0.0023(10) 0.0007(10) C9 0.0279(8) 0.0347(9) 0.0333(9) -0.0014(7) 0.0052(7) -0.0061(7) C10 0.0278(8) 0.0394(10) 0.0297(9) -0.0018(7) 0.0049(6) -0.0044(7) C11 0.0340(9) 0.0475(11) 0.0330(10) 0.0075(8) 0.0059(7) -0.0071(8) C12 0.0321(9) 0.0363(10) 0.0601(12) -0.0065(9) 0.0043(8) -0.0001(8) C13 0.0379(10) 0.0490(12) 0.0666(14) -0.0107(10) 0.0020(9) 0.0025(9) C14 0.0245(8) 0.0355(9) 0.0367(9) -0.0043(8) 0.0020(7) -0.0024(7) C15 0.0256(8) 0.0262(8) 0.0334(9) 0.0001(7) 0.0003(6) -0.0029(6) C16 0.0264(8) 0.0386(9) 0.0343(9) 0.0094(7) -0.0014(7) -0.0032(7) C17 0.0215(8) 0.0344(9) 0.0431(10) 0.0053(8) 0.0015(7) -0.0005(7) C18 0.0328(9) 0.0266(8) 0.0327(9) -0.0030(7) 0.0060(7) -0.0061(7) C19 0.0384(10) 0.0386(10) 0.0297(9) 0.0012(7) -0.0041(7) 0.0019(8) C20 0.0261(8) 0.0354(9) 0.0366(9) 0.0002(7) -0.0038(7) 0.0026(7) C21 0.0413(11) 0.0535(12) 0.0567(13) -0.0094(10) 0.0202(9) -0.0024(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 O1 C1 1.208(2) . ? O2 C1 1.335(2) . ? O2 C4 1.470(2) . ? O3 C3 1.414(2) . ? O3 C2 1.429(2) . ? O4 C3 1.408(2) . ? O4 C7 1.433(2) . ? O5 C4 1.389(2) . ? O5 C8 1.430(2) . ? O6 C11 1.212(2) . ? O7 C11 1.334(2) . ? O7 C13 1.455(2) . ? O8 C14 1.416(2) . ? O8 H8 0.96(2) . ? O9 C18 1.375(2) . ? O9 C21 1.427(2) . ? O10 H10B 0.89(2) . ? O10 H10A 0.87(2) . ? C1 C2 1.512(2) . ? C2 C9 1.531(2) . ? C2 H2 1.00 . ? C3 C5 1.507(2) . ? C3 C4 1.534(2) . ? C4 C6 1.509(2) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C8 H8D 0.98 . ? C9 C12 1.523(2) . ? C9 C10 1.540(2) . ? C9 H9 1.00 . ? C10 C11 1.521(2) . ? C10 C14 1.550(2) . ? C10 H10 1.00 . ? C12 C13 1.503(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.527(2) . ? C14 H14 1.00 . ? C15 C16 1.387(2) . ? C15 C20 1.390(2) . ? C16 C17 1.390(2) . ? C16 H16 0.95 . ? C17 C18 1.382(2) . ? C17 H17 0.95 . ? C18 C19 1.384(2) . ? C19 C20 1.385(2) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 118.51(12) . . ? C3 O3 C2 114.65(11) . . ? C3 O4 C7 114.57(13) . . ? C4 O5 C8 116.99(14) . . ? C11 O7 C13 121.00(15) . . ? C14 O8 H8 110.8(13) . . ? C18 O9 C21 117.30(14) . . ? H10B O10 H10A 107.6(20) . . ? O1 C1 O2 117.8(2) . . ? O1 C1 C2 120.93(15) . . ? O2 C1 C2 121.13(13) . . ? O3 C2 C1 115.49(12) . . ? O3 C2 C9 107.05(12) . . ? C1 C2 C9 111.34(13) . . ? O3 C2 H2 107.55(8) . . ? C1 C2 H2 107.55(9) . . ? C9 C2 H2 107.55(8) . . ? O4 C3 O3 110.60(12) . . ? O4 C3 C5 113.66(13) . . ? O3 C3 C5 106.42(13) . . ? O4 C3 C4 105.61(12) . . ? O3 C3 C4 108.25(12) . . ? C5 C3 C4 112.25(13) . . ? O5 C4 O2 107.83(12) . . ? O5 C4 C6 115.31(14) . . ? O2 C4 C6 104.54(13) . . ? O5 C4 C3 105.45(13) . . ? O2 C4 C3 109.12(12) . . ? C6 C4 C3 114.36(14) . . ? C3 C5 H5A 109.47(9) . . ? C3 C5 H5B 109.47(9) . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.47(9) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.47(10) . . ? C4 C6 H6B 109.47(10) . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.47(10) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.47(9) . . ? O4 C7 H7B 109.47(10) . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.47(9) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8B 109.47(10) . . ? O5 C8 H8C 109.47(9) . . ? H8B C8 H8C 109.5 . . ? O5 C8 H8D 109.47(10) . . ? H8B C8 H8D 109.5 . . ? H8C C8 H8D 109.5 . . ? C12 C9 C2 112.08(13) . . ? C12 C9 C10 110.88(14) . . ? C2 C9 C10 110.45(13) . . ? C12 C9 H9 107.75(9) . . ? C2 C9 H9 107.75(8) . . ? C10 C9 H9 107.75(8) . . ? C11 C10 C9 116.06(14) . . ? C11 C10 C14 108.99(13) . . ? C9 C10 C14 114.14(13) . . ? C11 C10 H10 105.56(8) . . ? C9 C10 H10 105.56(8) . . ? C14 C10 H10 105.56(8) . . ? O6 C11 O7 117.6(2) . . ? O6 C11 C10 120.5(2) . . ? O7 C11 C10 121.9(2) . . ? C13 C12 C9 109.86(15) . . ? C13 C12 H12A 109.69(11) . . ? C9 C12 H12A 109.69(10) . . ? C13 C12 H12B 109.69(12) . . ? C9 C12 H12B 109.69(9) . . ? H12A C12 H12B 108.2 . . ? O7 C13 C12 111.3(2) . . ? O7 C13 H13A 109.37(10) . . ? C12 C13 H13A 109.37(12) . . ? O7 C13 H13B 109.37(10) . . ? C12 C13 H13B 109.37(11) . . ? H13A C13 H13B 108.0 . . ? O8 C14 C15 112.42(14) . . ? O8 C14 C10 106.49(12) . . ? C15 C14 C10 112.78(13) . . ? O8 C14 H14 108.34(9) . . ? C15 C14 H14 108.34(8) . . ? C10 C14 H14 108.34(9) . . ? C16 C15 C20 117.55(14) . . ? C16 C15 C14 120.71(14) . . ? C20 C15 C14 121.74(14) . . ? C15 C16 C17 121.9(2) . . ? C15 C16 H16 119.04(9) . . ? C17 C16 H16 119.04(10) . . ? C18 C17 C16 119.37(15) . . ? C18 C17 H17 120.32(9) . . ? C16 C17 H17 120.32(10) . . ? O9 C18 C17 124.44(15) . . ? O9 C18 C19 115.78(15) . . ? C17 C18 C19 119.77(15) . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 119.93(10) . . ? C20 C19 H19 119.93(10) . . ? C19 C20 C15 121.25(15) . . ? C19 C20 H20 119.37(10) . . ? C15 C20 H20 119.37(9) . . ? O9 C21 H21A 109.47(10) . . ? O9 C21 H21B 109.47(10) . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.47(10) . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C4 O2 C1 O1 -169.7(2) . . . . ? C4 O2 C1 C2 14.6(2) . . . . ? C3 O3 C2 C1 32.5(2) . . . . ? C3 O3 C2 C9 157.13(12) . . . . ? O1 C1 C2 O3 175.6(2) . . . . ? O2 C1 C2 O3 -8.8(2) . . . . ? O1 C1 C2 C9 53.2(2) . . . . ? O2 C1 C2 C9 -131.1(2) . . . . ? C7 O4 C3 O3 65.1(2) . . . . ? C7 O4 C3 C5 -54.5(2) . . . . ? C7 O4 C3 C4 -178.00(13) . . . . ? C2 O3 C3 O4 56.5(2) . . . . ? C2 O3 C3 C5 -179.64(12) . . . . ? C2 O3 C3 C4 -58.8(2) . . . . ? C8 O5 C4 O2 65.9(2) . . . . ? C8 O5 C4 C6 -50.4(2) . . . . ? C8 O5 C4 C3 -177.60(13) . . . . ? C1 O2 C4 O5 74.0(2) . . . . ? C1 O2 C4 C6 -162.78(14) . . . . ? C1 O2 C4 C3 -40.0(2) . . . . ? O4 C3 C4 O5 -172.61(11) . . . . ? O3 C3 C4 O5 -54.13(15) . . . . ? C5 C3 C4 O5 63.0(2) . . . . ? O4 C3 C4 O2 -57.02(15) . . . . ? O3 C3 C4 O2 61.5(2) . . . . ? C5 C3 C4 O2 178.62(13) . . . . ? O4 C3 C4 C6 59.7(2) . . . . ? O3 C3 C4 C6 178.13(14) . . . . ? C5 C3 C4 C6 -64.7(2) . . . . ? O3 C2 C9 C12 -59.8(2) . . . . ? C1 C2 C9 C12 67.3(2) . . . . ? O3 C2 C9 C10 64.4(2) . . . . ? C1 C2 C9 C10 -168.49(13) . . . . ? C12 C9 C10 C11 -23.0(2) . . . . ? C2 C9 C10 C11 -147.87(13) . . . . ? C12 C9 C10 C14 -151.03(13) . . . . ? C2 C9 C10 C14 84.1(2) . . . . ? C13 O7 C11 O6 177.7(2) . . . . ? C13 O7 C11 C10 -3.3(2) . . . . ? C9 C10 C11 O6 176.15(15) . . . . ? C14 C10 C11 O6 -53.3(2) . . . . ? C9 C10 C11 O7 -2.9(2) . . . . ? C14 C10 C11 O7 127.7(2) . . . . ? C2 C9 C12 C13 177.81(15) . . . . ? C10 C9 C12 C13 53.9(2) . . . . ? C11 O7 C13 C12 35.4(2) . . . . ? C9 C12 C13 O7 -60.8(2) . . . . ? C11 C10 C14 O8 161.36(13) . . . . ? C9 C10 C14 O8 -67.1(2) . . . . ? C11 C10 C14 C15 -74.9(2) . . . . ? C9 C10 C14 C15 56.7(2) . . . . ? O8 C14 C15 C16 -168.72(15) . . . . ? C10 C14 C15 C16 70.9(2) . . . . ? O8 C14 C15 C20 11.5(2) . . . . ? C10 C14 C15 C20 -108.9(2) . . . . ? C20 C15 C16 C17 0.2(3) . . . . ? C14 C15 C16 C17 -179.6(2) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C21 O9 C18 C17 -0.3(2) . . . . ? C21 O9 C18 C19 178.8(2) . . . . ? C16 C17 C18 O9 179.50(15) . . . . ? C16 C17 C18 C19 0.5(2) . . . . ? O9 C18 C19 C20 -178.48(15) . . . . ? C17 C18 C19 C20 0.6(3) . . . . ? C18 C19 C20 C15 -1.3(3) . . . . ? C16 C15 C20 C19 0.9(3) . . . . ? C14 C15 C20 C19 -179.3(2) . . . . ? _refine_diff_density_max 0.354 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.058 data_sl0438 _database_code_depnum_ccdc_archive 'CCDC 283219' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H34 O7' _chemical_formula_sum 'C20 H34 O7' _chemical_formula_weight 386.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.2857(3) _cell_length_b 10.4352(3) _cell_length_c 21.1270(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2047.17(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 41035 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 1.001 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen was NOT located: instead, it was placed in a reasonable position with SHELXL. 1899 Friedel pairs averaged for the refinement. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12532 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2621 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1371P)^2^+0.2194P] 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 1(2) _refine_ls_number_reflns 2621 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.3539(4) 0.8241(3) 0.49396(14) 0.0464(8) Uani 1 1 d . . . O2 O 0.2375(3) 0.6647(3) 0.63568(13) 0.0367(7) Uani 1 1 d . . . O3 O 0.4649(3) 0.6764(3) 0.54851(12) 0.0355(6) Uani 1 1 d . . . O4 O 0.2623(3) 0.4907(3) 0.56727(16) 0.0445(8) Uani 1 1 d . . . O5 O 0.5219(3) 0.6633(3) 0.65569(14) 0.0395(7) Uani 1 1 d . . . O6 O -0.0117(4) 0.7476(4) 0.73582(19) 0.0682(11) Uani 1 1 d . . . O7 O -0.1222(4) 1.0269(4) 0.69868(18) 0.0675(11) Uani 1 1 d . . . H7A H -0.0932 1.0882 0.7211 0.101 Uiso 1 1 calc R . . C1 C 0.1909(4) 0.8838(4) 0.61111(18) 0.0336(8) Uani 1 1 d . . . H1 H 0.1771 0.9418 0.5739 0.040 Uiso 1 1 calc R . . C2 C 0.2235(4) 0.7510(4) 0.5839(2) 0.0362(9) Uani 1 1 d . . . H2 H 0.1376 0.7236 0.5588 0.043 Uiso 1 1 calc R . . C7 C -0.1639(6) 1.1714(5) 0.5759(3) 0.0561(12) Uani 1 1 d . . . H7B H -0.2270 1.1774 0.5388 0.084 Uiso 1 1 calc R . . H7C H -0.0789 1.2255 0.5694 0.084 Uiso 1 1 calc R . . H7D H -0.2161 1.2004 0.6136 0.084 Uiso 1 1 calc R . . C8 C -0.1170(6) 1.0332(4) 0.5849(2) 0.0474(11) Uani 1 1 d . . . H8A H -0.2034 0.9776 0.5861 0.057 Uiso 1 1 calc R . . H8B H -0.0578 1.0066 0.5482 0.057 Uiso 1 1 calc R . . C9 C -0.0308(5) 1.0134(4) 0.64512(19) 0.0378(9) Uani 1 1 d . . . H9 H 0.0450 1.0813 0.6473 0.045 Uiso 1 1 calc R . . C10 C 0.0444(4) 0.8812(4) 0.64682(19) 0.0356(9) Uani 1 1 d . . . H10 H -0.0195 0.8190 0.6243 0.043 Uiso 1 1 calc R . . C11 C 0.0612(5) 0.8348(6) 0.7138(2) 0.0531(12) Uani 1 1 d . . . C12 C 0.1748(6) 0.9039(7) 0.7511(2) 0.0664(16) Uani 1 1 d . . . H12A H 0.1473 0.9951 0.7557 0.080 Uiso 1 1 calc R . . H12B H 0.1813 0.8661 0.7940 0.080 Uiso 1 1 calc R . . C13 C 0.3173(6) 0.8952(6) 0.7196(2) 0.0564(12) Uani 1 1 d . . . H13A H 0.3504 0.8051 0.7211 0.068 Uiso 1 1 calc R . . H13B H 0.3873 0.9474 0.7438 0.068 Uiso 1 1 calc R . . C14 C 0.3182(4) 0.9407(4) 0.64976(19) 0.0351(8) Uani 1 1 d . . . H14 H 0.4059 0.9000 0.6311 0.042 Uiso 1 1 calc R . . C18 C 0.3449(6) 1.0870(5) 0.6427(3) 0.0547(13) Uani 1 1 d . . . H18 H 0.2696 1.1311 0.6686 0.066 Uiso 1 1 calc R . . C19 C 0.3301(10) 1.1353(7) 0.5777(3) 0.091(3) Uani 1 1 d . . . H19A H 0.3591 1.2256 0.5762 0.137 Uiso 1 1 calc R . . H19B H 0.2295 1.1274 0.5641 0.137 Uiso 1 1 calc R . . H19C H 0.3918 1.0852 0.5493 0.137 Uiso 1 1 calc R . . C20 C 0.4891(6) 1.1238(5) 0.6708(3) 0.0625(15) Uani 1 1 d . . . H20A H 0.5076 1.2148 0.6628 0.094 Uiso 1 1 calc R . . H20B H 0.5652 1.0722 0.6512 0.094 Uiso 1 1 calc R . . H20C H 0.4878 1.1082 0.7165 0.094 Uiso 1 1 calc R . . C21 C 0.3520(4) 0.7551(4) 0.53885(19) 0.0356(9) Uani 1 1 d . . . C22 C 0.4723(5) 0.5930(4) 0.60374(19) 0.0365(9) Uani 1 1 d . . . C23 C 0.3174(5) 0.5519(4) 0.6224(2) 0.0379(9) Uani 1 1 d . . . C24 C 0.3111(5) 0.4703(4) 0.6810(2) 0.0468(10) Uani 1 1 d . . . H24A H 0.2103 0.4564 0.6930 0.070 Uiso 1 1 calc R . . H24B H 0.3617 0.5137 0.7156 0.070 Uiso 1 1 calc R . . H24C H 0.3571 0.3875 0.6726 0.070 Uiso 1 1 calc R . . C25 C 0.5700(5) 0.4837(4) 0.5840(2) 0.0423(10) Uani 1 1 d . . . H25A H 0.6564 0.5183 0.5635 0.063 Uiso 1 1 calc R . . H25B H 0.5188 0.4279 0.5542 0.063 Uiso 1 1 calc R . . H25C H 0.5980 0.4342 0.6214 0.063 Uiso 1 1 calc R . . C26 C 0.1160(6) 0.4483(6) 0.5723(3) 0.0653(15) Uani 1 1 d . . . H26A H 0.0790 0.4274 0.5301 0.098 Uiso 1 1 calc R . . H26B H 0.0572 0.5165 0.5910 0.098 Uiso 1 1 calc R . . H26C H 0.1116 0.3719 0.5993 0.098 Uiso 1 1 calc R . . C27 C 0.6668(5) 0.7106(5) 0.6507(3) 0.0498(11) Uani 1 1 d . . . H27A H 0.6877 0.7664 0.6868 0.075 Uiso 1 1 calc R . . H27B H 0.6773 0.7592 0.6113 0.075 Uiso 1 1 calc R . . H27C H 0.7341 0.6382 0.6506 0.075 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 0.0543(18) 0.0485(17) 0.0363(15) 0.0086(14) 0.0010(13) 0.0053(15) O2 0.0388(14) 0.0326(14) 0.0386(15) 0.0018(12) 0.0048(12) -0.0015(12) O3 0.0351(14) 0.0391(14) 0.0322(14) 0.0023(12) 0.0035(11) 0.0013(13) O4 0.0431(16) 0.0382(15) 0.0521(18) -0.0088(14) -0.0054(14) -0.0058(13) O5 0.0375(14) 0.0419(15) 0.0389(15) -0.0012(13) -0.0024(12) -0.0066(13) O6 0.051(2) 0.084(3) 0.070(3) 0.034(2) 0.0080(18) -0.013(2) O7 0.066(2) 0.081(3) 0.056(2) -0.015(2) 0.0107(18) 0.000(2) C1 0.035(2) 0.0339(18) 0.0322(18) 0.0038(16) 0.0013(16) 0.0023(17) C2 0.038(2) 0.0326(19) 0.038(2) -0.0013(17) -0.0031(17) -0.0045(16) C7 0.059(3) 0.045(2) 0.065(3) 0.010(2) -0.006(3) 0.002(2) C8 0.054(3) 0.040(2) 0.048(2) -0.006(2) -0.006(2) 0.009(2) C9 0.0356(19) 0.042(2) 0.036(2) -0.0076(18) 0.0032(17) -0.0012(17) C10 0.0319(19) 0.042(2) 0.0331(19) -0.0001(18) 0.0041(16) -0.0005(16) C11 0.038(2) 0.071(3) 0.051(3) 0.018(3) 0.006(2) 0.002(2) C12 0.063(3) 0.102(5) 0.034(2) 0.017(3) -0.002(2) -0.013(3) C13 0.059(3) 0.066(3) 0.044(2) 0.007(2) -0.006(2) -0.007(3) C14 0.0339(19) 0.0335(19) 0.038(2) 0.0001(17) -0.0002(18) -0.0025(16) C18 0.062(3) 0.038(2) 0.063(3) 0.004(2) -0.009(3) -0.012(2) C19 0.144(7) 0.066(4) 0.064(3) 0.025(3) -0.023(4) -0.052(4) C20 0.051(3) 0.041(2) 0.096(4) 0.016(3) -0.018(3) -0.012(2) C21 0.041(2) 0.0314(19) 0.034(2) -0.0042(17) -0.0015(17) 0.0009(17) C22 0.042(2) 0.032(2) 0.035(2) 0.0069(16) -0.0010(17) -0.0029(17) C23 0.041(2) 0.0292(18) 0.043(2) -0.0006(17) -0.0009(19) -0.0015(17) C24 0.050(2) 0.040(2) 0.050(2) 0.011(2) 0.009(2) 0.000(2) C25 0.043(2) 0.039(2) 0.045(2) 0.002(2) 0.0052(19) 0.0050(18) C26 0.052(3) 0.054(3) 0.090(4) -0.014(3) -0.009(3) -0.011(3) C27 0.041(2) 0.053(3) 0.056(3) -0.002(2) -0.008(2) -0.010(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 1.191(5) . ? O2 C23 1.419(5) . ? O2 C2 1.422(5) . ? O3 C21 1.347(5) . ? O3 C22 1.457(5) . ? O4 C23 1.423(5) . ? O4 C26 1.434(7) . ? O5 C22 1.398(5) . ? O5 C27 1.436(6) . ? O6 C11 1.226(6) . ? O7 C9 1.422(6) . ? O7 H7A 0.8400 . ? C1 C2 1.530(6) . ? C1 C14 1.554(6) . ? C1 C10 1.556(6) . ? C1 H1 1.0000 . ? C2 C21 1.528(6) . ? C2 H2 1.0000 . ? C7 C8 1.519(7) . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 H7D 0.9800 . ? C8 C9 1.517(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.546(6) . ? C9 H9 1.0000 . ? C10 C11 1.504(6) . ? C10 H10 1.0000 . ? C11 C12 1.501(8) . ? C12 C13 1.485(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.549(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C18 1.554(6) . ? C14 H14 1.0000 . ? C18 C19 1.470(8) . ? C18 C20 1.514(7) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C22 C25 1.515(6) . ? C22 C23 1.552(6) . ? C23 C24 1.504(6) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C23 O2 C2 114.9(3) . . ? C21 O3 C22 121.5(3) . . ? C23 O4 C26 114.7(4) . . ? C22 O5 C27 115.5(4) . . ? C9 O7 H7A 109.5 . . ? C2 C1 C14 113.1(3) . . ? C2 C1 C10 109.8(3) . . ? C14 C1 C10 114.6(3) . . ? C2 C1 H1 106.2 . . ? C14 C1 H1 106.2 . . ? C10 C1 H1 106.2 . . ? O2 C2 C21 115.2(3) . . ? O2 C2 C1 107.6(3) . . ? C21 C2 C1 111.2(3) . . ? O2 C2 H2 107.5 . . ? C21 C2 H2 107.5 . . ? C1 C2 H2 107.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7D 109.5 . . ? H7B C7 H7D 109.5 . . ? H7C C7 H7D 109.5 . . ? C9 C8 C7 112.7(4) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O7 C9 C8 109.8(4) . . ? O7 C9 C10 109.9(4) . . ? C8 C9 C10 112.3(3) . . ? O7 C9 H9 108.3 . . ? C8 C9 H9 108.3 . . ? C10 C9 H9 108.3 . . ? C11 C10 C9 110.9(4) . . ? C11 C10 C1 111.8(3) . . ? C9 C10 C1 111.6(3) . . ? C11 C10 H10 107.4 . . ? C9 C10 H10 107.4 . . ? C1 C10 H10 107.4 . . ? O6 C11 C12 123.0(5) . . ? O6 C11 C10 122.7(5) . . ? C12 C11 C10 114.3(4) . . ? C13 C12 C11 111.2(5) . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 114.4(4) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C18 113.1(4) . . ? C13 C14 C1 112.3(4) . . ? C18 C14 C1 116.5(4) . . ? C13 C14 H14 104.5 . . ? C18 C14 H14 104.5 . . ? C1 C14 H14 104.5 . . ? C19 C18 C20 111.2(5) . . ? C19 C18 C14 114.3(4) . . ? C20 C18 C14 110.7(4) . . ? C19 C18 H18 106.7 . . ? C20 C18 H18 106.7 . . ? C14 C18 H18 106.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 O3 118.5(4) . . ? O1 C21 C2 121.7(4) . . ? O3 C21 C2 119.7(3) . . ? O5 C22 O3 109.3(3) . . ? O5 C22 C25 114.5(4) . . ? O3 C22 C25 104.9(3) . . ? O5 C22 C23 104.5(3) . . ? O3 C22 C23 108.9(3) . . ? C25 C22 C23 114.6(3) . . ? O2 C23 O4 110.3(3) . . ? O2 C23 C24 106.6(3) . . ? O4 C23 C24 113.9(3) . . ? O2 C23 C22 107.8(3) . . ? O4 C23 C22 104.4(3) . . ? C24 C23 C22 113.7(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C23 O2 C2 C21 -33.2(5) . . . . ? C23 O2 C2 C1 -157.9(3) . . . . ? C14 C1 C2 O2 66.4(4) . . . . ? C10 C1 C2 O2 -63.1(4) . . . . ? C14 C1 C2 C21 -60.7(4) . . . . ? C10 C1 C2 C21 169.9(3) . . . . ? C7 C8 C9 O7 70.0(5) . . . . ? C7 C8 C9 C10 -167.4(4) . . . . ? O7 C9 C10 C11 -28.0(5) . . . . ? C8 C9 C10 C11 -150.5(4) . . . . ? O7 C9 C10 C1 -153.3(3) . . . . ? C8 C9 C10 C1 84.2(4) . . . . ? C2 C1 C10 C11 84.4(5) . . . . ? C14 C1 C10 C11 -44.3(5) . . . . ? C2 C1 C10 C9 -150.8(3) . . . . ? C14 C1 C10 C9 80.5(4) . . . . ? C9 C10 C11 O6 106.9(6) . . . . ? C1 C10 C11 O6 -127.8(5) . . . . ? C9 C10 C11 C12 -73.2(5) . . . . ? C1 C10 C11 C12 52.0(6) . . . . ? O6 C11 C12 C13 122.5(6) . . . . ? C10 C11 C12 C13 -57.3(7) . . . . ? C11 C12 C13 C14 54.1(7) . . . . ? C12 C13 C14 C18 87.5(6) . . . . ? C12 C13 C14 C1 -46.9(6) . . . . ? C2 C1 C14 C13 -85.4(4) . . . . ? C10 C1 C14 C13 41.6(5) . . . . ? C2 C1 C14 C18 141.8(4) . . . . ? C10 C1 C14 C18 -91.2(5) . . . . ? C13 C14 C18 C19 -173.4(6) . . . . ? C1 C14 C18 C19 -41.1(7) . . . . ? C13 C14 C18 C20 60.1(6) . . . . ? C1 C14 C18 C20 -167.6(4) . . . . ? C22 O3 C21 O1 177.7(4) . . . . ? C22 O3 C21 C2 -4.4(5) . . . . ? O2 C2 C21 O1 -179.5(4) . . . . ? C1 C2 C21 O1 -56.6(5) . . . . ? O2 C2 C21 O3 2.6(5) . . . . ? C1 C2 C21 O3 125.4(4) . . . . ? C27 O5 C22 O3 -64.9(4) . . . . ? C27 O5 C22 C25 52.4(5) . . . . ? C27 O5 C22 C23 178.7(3) . . . . ? C21 O3 C22 O5 -81.6(4) . . . . ? C21 O3 C22 C25 155.2(4) . . . . ? C21 O3 C22 C23 32.0(5) . . . . ? C2 O2 C23 O4 -52.0(4) . . . . ? C2 O2 C23 C24 -176.2(3) . . . . ? C2 O2 C23 C22 61.4(4) . . . . ? C26 O4 C23 O2 -62.1(5) . . . . ? C26 O4 C23 C24 57.8(5) . . . . ? C26 O4 C23 C22 -177.7(4) . . . . ? O5 C22 C23 O2 57.5(4) . . . . ? O3 C22 C23 O2 -59.2(4) . . . . ? C25 C22 C23 O2 -176.4(3) . . . . ? O5 C22 C23 O4 174.8(3) . . . . ? O3 C22 C23 O4 58.0(4) . . . . ? C25 C22 C23 O4 -59.1(4) . . . . ? O5 C22 C23 C24 -60.5(4) . . . . ? O3 C22 C23 C24 -177.2(3) . . . . ? C25 C22 C23 C24 65.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.644 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.077 data_sl0019 _database_code_depnum_ccdc_archive 'CCDC 283220' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H21 N O7' _chemical_formula_weight 339.34 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 19.0707(7) _cell_length_b 13.0777(3) _cell_length_c 27.3853(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6829.9(4) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 24737 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method ? _exptl_crystal_F_000 2880 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 1.069 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30161 _diffrn_reflns_av_R_equivalents 0.1038 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5991 _reflns_number_observed 3363 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 17 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.5416P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5974 _refine_ls_number_parameters 441 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1362 _refine_ls_R_factor_obs 0.0546 _refine_ls_wR_factor_all 0.1867 _refine_ls_wR_factor_obs 0.1189 _refine_ls_goodness_of_fit_all 1.013 _refine_ls_goodness_of_fit_obs 1.139 _refine_ls_restrained_S_all 1.304 _refine_ls_restrained_S_obs 1.139 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1_1 O 0.76966(10) 0.24206(13) 0.29971(7) 0.0515(5) Uani 1 d . . O2_1 O 0.69368(9) 0.20528(11) 0.24247(6) 0.0391(5) Uani 1 d . . O3_1 O 0.72923(9) -0.00237(11) 0.24787(6) 0.0344(4) Uani 1 d . . O4_1 O 0.61788(9) 0.03914(12) 0.27496(7) 0.0457(5) Uani 1 d . . O5_1 O 0.70705(11) 0.11952(13) 0.16941(7) 0.0516(5) Uani 1 d . . C1_1 C 0.74257(14) 0.1776(2) 0.27464(9) 0.0349(6) Uani 1 d . . C2_1 C 0.75916(13) 0.0649(2) 0.28256(9) 0.0327(6) Uani 1 d . . H2_1 H 0.73953(13) 0.0457(2) 0.31515(9) 0.039 Uiso 1 calc R . C3_1 C 0.66008(13) 0.0247(2) 0.23386(9) 0.0343(6) Uani 1 d . . C4_1 C 0.66217(14) 0.1303(2) 0.20875(9) 0.0371(7) Uani 1 d . . C5_1 C 0.6358(2) -0.0594(2) 0.19986(11) 0.0498(8) Uani 1 d . . H5A_1 H 0.6434(9) -0.1260(2) 0.2154(3) 0.075 Uiso 1 calc R . H5B_1 H 0.6626(7) -0.0561(9) 0.1693(3) 0.075 Uiso 1 calc R . H5C_1 H 0.5858(3) -0.0507(8) 0.1928(5) 0.075 Uiso 1 calc R . C6_1 C 0.5905(2) 0.1727(2) 0.19675(12) 0.0574(8) Uani 1 d . . H6A_1 H 0.5951(2) 0.2438(5) 0.1859(7) 0.086 Uiso 1 calc R . H6B_1 H 0.5608(3) 0.1700(13) 0.2259(2) 0.086 Uiso 1 calc R . H6C_1 H 0.5692(4) 0.1318(9) 0.1707(5) 0.086 Uiso 1 calc R . C7_1 C 0.6035(2) -0.0511(2) 0.30341(13) 0.0696(10) Uani 1 d . . H7A_1 H 0.5901(11) -0.0311(2) 0.3366(3) 0.104 Uiso 1 calc R . H7B_1 H 0.6456(4) -0.0940(9) 0.3047(7) 0.104 Uiso 1 calc R . H7C_1 H 0.5651(8) -0.0895(9) 0.2883(5) 0.104 Uiso 1 calc R . C8_1 C 0.7182(2) 0.2091(2) 0.14028(12) 0.0878(13) Uani 1 d . . H8A_1 H 0.7531(11) 0.1944(7) 0.1150(6) 0.132 Uiso 1 calc R . H8B_1 H 0.7350(14) 0.2649(6) 0.1611(2) 0.132 Uiso 1 calc R . H8C_1 H 0.6739(4) 0.2292(12) 0.1248(8) 0.132 Uiso 1 calc R . C9_1 C 0.83803(13) 0.0453(2) 0.28472(9) 0.0316(6) Uani 1 d . . H9_1 H 0.85868(13) 0.0974(2) 0.30724(9) 0.038 Uiso 1 calc R . C10_1 C 0.84926(13) -0.0596(2) 0.30811(10) 0.0358(6) Uani 1 d . . H10A_1 H 0.82254(13) -0.0641(2) 0.33903(10) 0.043 Uiso 1 calc R . H10B_1 H 0.83230(13) -0.1139(2) 0.28589(10) 0.043 Uiso 1 calc R . N1_1 N 0.92538(13) -0.0736(2) 0.31790(9) 0.0462(6) Uani 1 d . . O6_1 O 0.95689(12) -0.1409(2) 0.29686(10) 0.0744(7) Uani 1 d . . O7_1 O 0.95290(12) -0.0160(2) 0.34724(9) 0.0730(7) Uani 1 d . . C11_1 C 0.87480(12) 0.0562(2) 0.23591(9) 0.0304(6) Uani 1 d . . C12_1 C 0.87473(14) -0.0218(2) 0.20136(10) 0.0392(7) Uani 1 d . . H12_1 H 0.84901(14) -0.0826(2) 0.20764(10) 0.047 Uiso 1 calc R . C13_1 C 0.9111(2) -0.0124(2) 0.15846(10) 0.0450(7) Uani 1 d . . H13_1 H 0.9110(2) -0.0671(2) 0.13562(10) 0.054 Uiso 1 calc R . C14_1 C 0.9477(2) 0.0758(2) 0.14822(10) 0.0481(8) Uani 1 d . . H14_1 H 0.9730(2) 0.0822(2) 0.11846(10) 0.058 Uiso 1 calc R . C15_1 C 0.9474(2) 0.1543(2) 0.18150(11) 0.0504(8) Uani 1 d . . H15_1 H 0.9717(2) 0.2160(2) 0.17438(11) 0.060 Uiso 1 calc R . C16_1 C 0.91215(14) 0.1442(2) 0.22520(10) 0.0418(7) Uani 1 d . . H16_1 H 0.91350(14) 0.1984(2) 0.24829(10) 0.050 Uiso 1 calc R . O1_2 O 0.77629(12) -0.03731(14) 0.41402(7) 0.0614(6) Uani 1 d . . O2_2 O 0.70111(10) 0.00288(12) 0.47113(6) 0.0421(5) Uani 1 d . . O3_2 O 0.72625(9) 0.21146(11) 0.45626(6) 0.0385(5) Uani 1 d . . O4_2 O 0.62046(10) 0.14860(13) 0.42752(7) 0.0522(5) Uani 1 d . . O5_2 O 0.70639(10) 0.10718(13) 0.53981(7) 0.0496(5) Uani 1 d . . C1_2 C 0.7480(2) 0.0293(2) 0.43727(10) 0.0403(7) Uani 1 d . . C2_2 C 0.76295(14) 0.1407(2) 0.42670(9) 0.0365(7) Uani 1 d . . H2_2 H 0.74855(14) 0.1538(2) 0.39215(9) 0.044 Uiso 1 calc R . C3_2 C 0.65786(14) 0.1786(2) 0.46944(10) 0.0401(7) Uani 1 d . . C4_2 C 0.66450(14) 0.0810(2) 0.50019(9) 0.0388(7) Uani 1 d . . C5_2 C 0.6246(2) 0.2662(2) 0.49712(12) 0.0615(9) Uani 1 d . . H5A_2 H 0.6279(10) 0.3289(4) 0.4776(3) 0.092 Uiso 1 calc R . H5B_2 H 0.6492(7) 0.2760(10) 0.5282(4) 0.092 Uiso 1 calc R . H5C_2 H 0.5752(3) 0.2506(7) 0.5035(6) 0.092 Uiso 1 calc R . C6_2 C 0.5955(2) 0.0320(2) 0.51336(11) 0.0512(8) Uani 1 d . . H6A_2 H 0.6042(2) -0.0333(7) 0.5298(6) 0.077 Uiso 1 calc R . H6B_2 H 0.5681(4) 0.0202(12) 0.48361(12) 0.077 Uiso 1 calc R . H6C_2 H 0.5694(4) 0.0774(6) 0.5353(5) 0.077 Uiso 1 calc R . C7_2 C 0.6076(2) 0.2279(3) 0.39256(13) 0.0743(11) Uani 1 d . . H7A_2 H 0.5968(12) 0.1973(3) 0.3608(2) 0.111 Uiso 1 calc R . H7B_2 H 0.6493(5) 0.2712(11) 0.3896(6) 0.111 Uiso 1 calc R . H7C_2 H 0.5678(8) 0.2696(11) 0.4034(4) 0.111 Uiso 1 calc R . C8_2 C 0.7313(2) 0.0251(2) 0.57000(11) 0.0623(9) Uani 1 d . . H8A_2 H 0.7599(9) 0.0529(3) 0.5966(4) 0.093 Uiso 1 calc R . H8B_2 H 0.7597(9) -0.0218(9) 0.5503(2) 0.093 Uiso 1 calc R . H8C_2 H 0.6912(2) -0.0120(10) 0.5837(6) 0.093 Uiso 1 calc R . C9_2 C 0.84145(14) 0.1635(2) 0.43014(9) 0.0374(7) Uani 1 d . . H9_2 H 0.86626(14) 0.1126(2) 0.40901(9) 0.045 Uiso 1 calc R . C10_2 C 0.85502(15) 0.2693(2) 0.40859(10) 0.0431(7) Uani 1 d . . H10A_2 H 0.83298(15) 0.2741(2) 0.37594(10) 0.052 Uiso 1 calc R . H10B_2 H 0.83372(15) 0.3221(2) 0.42982(10) 0.052 Uiso 1 calc R . N1_2 N 0.93183(15) 0.2880(2) 0.40428(10) 0.0583(7) Uani 1 d . . O6_2 O 0.9661(2) 0.2283(2) 0.3833(2) 0.196(2) Uani 1 d . . O7_2 O 0.95605(13) 0.3650(2) 0.41952(10) 0.0891(8) Uani 1 d . . C11_2 C 0.87004(14) 0.1517(2) 0.48134(9) 0.0369(6) Uani 1 d . . C12_2 C 0.9047(2) 0.0628(2) 0.49441(12) 0.0560(8) Uani 1 d . . H12_2 H 0.9109(2) 0.0101(2) 0.47094(12) 0.067 Uiso 1 calc R . C13_2 C 0.9306(2) 0.0499(3) 0.5412(2) 0.0767(11) Uani 1 d . . H13_2 H 0.9534(2) -0.0121(3) 0.5498(2) 0.092 Uiso 1 calc R . C14_2 C 0.9233(2) 0.1267(4) 0.57542(14) 0.0814(12) Uani 1 d . . H14_2 H 0.9421(2) 0.1189(4) 0.60733(14) 0.098 Uiso 1 calc R . C15_2 C 0.8887(2) 0.2141(3) 0.56262(12) 0.0665(10) Uani 1 d . . H15_2 H 0.8832(2) 0.2672(3) 0.58602(12) 0.080 Uiso 1 calc R . C16_2 C 0.8617(2) 0.2267(2) 0.51653(10) 0.0502(8) Uani 1 d . . H16_2 H 0.8370(2) 0.2876(2) 0.50870(10) 0.060 Uiso 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_1 0.0592(14) 0.0335(10) 0.0618(13) -0.0135(10) -0.0189(11) 0.0059(9) O2_1 0.0445(12) 0.0280(9) 0.0446(11) -0.0020(8) -0.0102(9) 0.0059(8) O3_1 0.0303(11) 0.0296(9) 0.0432(10) -0.0051(8) -0.0034(8) 0.0015(7) O4_1 0.0397(12) 0.0420(10) 0.0555(12) 0.0083(9) 0.0117(10) 0.0068(8) O5_1 0.072(2) 0.0412(11) 0.0414(11) 0.0036(9) 0.0074(11) -0.0029(9) C1_1 0.037(2) 0.0314(14) 0.0364(15) -0.0040(13) -0.0021(14) 0.0062(12) C2_1 0.037(2) 0.0302(14) 0.0306(14) -0.0003(11) -0.0028(12) 0.0020(11) C3_1 0.027(2) 0.0350(14) 0.041(2) -0.0018(12) -0.0015(13) 0.0015(11) C4_1 0.039(2) 0.0348(15) 0.037(2) -0.0013(12) -0.0067(13) -0.0011(12) C5_1 0.044(2) 0.039(2) 0.067(2) -0.0050(14) -0.010(2) -0.0045(13) C6_1 0.054(2) 0.049(2) 0.069(2) 0.007(2) -0.023(2) 0.0069(14) C7_1 0.069(2) 0.056(2) 0.084(2) 0.026(2) 0.027(2) 0.005(2) C8_1 0.148(4) 0.059(2) 0.057(2) 0.015(2) 0.025(2) -0.008(2) C9_1 0.036(2) 0.0231(12) 0.0361(15) -0.0010(11) -0.0051(12) 0.0005(10) C10_1 0.030(2) 0.0342(14) 0.043(2) 0.0068(12) -0.0018(13) 0.0025(11) N1_1 0.043(2) 0.0391(14) 0.056(2) 0.0167(13) -0.0030(13) 0.0060(12) O6_1 0.0557(15) 0.0576(13) 0.110(2) 0.0014(14) 0.0073(14) 0.0228(12) O7_1 0.057(2) 0.076(2) 0.086(2) -0.0022(13) -0.0310(13) 0.0002(12) C11_1 0.028(2) 0.0279(13) 0.0350(15) 0.0031(11) -0.0054(12) 0.0024(10) C12_1 0.042(2) 0.0322(14) 0.043(2) -0.0018(13) 0.0043(14) -0.0047(12) C13_1 0.050(2) 0.044(2) 0.040(2) -0.0061(13) 0.0027(15) 0.0009(14) C14_1 0.049(2) 0.057(2) 0.038(2) 0.0087(15) 0.0044(14) 0.0001(15) C15_1 0.053(2) 0.045(2) 0.054(2) 0.009(2) 0.010(2) -0.0124(14) C16_1 0.044(2) 0.0310(14) 0.050(2) -0.0008(13) -0.0004(15) -0.0046(12) O1_2 0.083(2) 0.0387(11) 0.0624(14) -0.0142(10) 0.0303(12) -0.0125(10) O2_2 0.0499(12) 0.0288(9) 0.0475(11) 0.0020(8) 0.0133(10) -0.0023(8) O3_2 0.0421(12) 0.0267(9) 0.0466(11) -0.0003(8) -0.0033(9) -0.0034(8) O4_2 0.0474(13) 0.0525(11) 0.0566(13) 0.0171(10) -0.0157(10) -0.0115(9) O5_2 0.0572(14) 0.0505(11) 0.0412(11) 0.0014(9) -0.0067(10) 0.0020(9) C1_2 0.049(2) 0.036(2) 0.037(2) -0.0052(13) 0.0036(15) -0.0080(13) C2_2 0.048(2) 0.0335(14) 0.0282(14) 0.0006(11) -0.0015(13) -0.0060(12) C3_2 0.037(2) 0.0328(15) 0.050(2) 0.0035(13) -0.0041(14) -0.0014(12) C4_2 0.043(2) 0.0357(15) 0.038(2) -0.0020(12) 0.0036(14) 0.0025(12) C5_2 0.060(2) 0.037(2) 0.087(2) 0.001(2) 0.008(2) 0.0102(14) C6_2 0.051(2) 0.049(2) 0.054(2) 0.0064(14) 0.010(2) -0.0037(14) C7_2 0.065(2) 0.077(2) 0.080(3) 0.039(2) -0.027(2) -0.009(2) C8_2 0.061(2) 0.078(2) 0.048(2) 0.022(2) -0.002(2) 0.011(2) C9_2 0.046(2) 0.0298(13) 0.036(2) -0.0016(11) 0.0056(13) -0.0036(12) C10_2 0.047(2) 0.042(2) 0.040(2) 0.0048(12) 0.0004(14) -0.0114(13) N1_2 0.063(2) 0.047(2) 0.065(2) 0.0027(14) 0.0218(15) -0.0096(14) O6_2 0.127(3) 0.097(2) 0.363(6) -0.092(3) 0.167(4) -0.043(2) O7_2 0.070(2) 0.093(2) 0.105(2) -0.025(2) -0.0028(15) -0.0391(14) C11_2 0.035(2) 0.0359(15) 0.040(2) 0.0012(13) 0.0008(13) -0.0004(12) C12_2 0.045(2) 0.051(2) 0.072(2) 0.013(2) 0.006(2) 0.0032(15) C13_2 0.051(2) 0.086(3) 0.093(3) 0.045(2) -0.008(2) 0.005(2) C14_2 0.045(2) 0.147(4) 0.052(2) 0.036(3) -0.009(2) -0.011(2) C15_2 0.054(2) 0.101(3) 0.045(2) -0.006(2) -0.011(2) -0.008(2) C16_2 0.049(2) 0.056(2) 0.046(2) -0.0011(15) -0.007(2) -0.0010(14) _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_1 C1_1 1.204(3) . ? O2_1 C1_1 1.333(3) . ? O2_1 C4_1 1.475(3) . ? O3_1 C2_1 1.415(3) . ? O3_1 C3_1 1.418(3) . ? O4_1 C3_1 1.396(3) . ? O4_1 C7_1 1.440(3) . ? O5_1 C4_1 1.383(3) . ? O5_1 C8_1 1.433(3) . ? C1_1 C2_1 1.523(3) . ? C2_1 C9_1 1.527(3) . ? C2_1 H2_1 1.00 . ? C3_1 C5_1 1.514(3) . ? C3_1 C4_1 1.543(3) . ? C4_1 C6_1 1.511(4) . ? C5_1 H5A_1 0.98 . ? C5_1 H5B_1 0.98 . ? C5_1 H5C_1 0.98 . ? C6_1 H6A_1 0.98 . ? C6_1 H6B_1 0.98 . ? C6_1 H6C_1 0.98 . ? C7_1 H7A_1 0.98 . ? C7_1 H7B_1 0.98 . ? C7_1 H7C_1 0.98 . ? C8_1 H8A_1 0.98 . ? C8_1 H8B_1 0.98 . ? C8_1 H8C_1 0.98 . ? C9_1 C11_1 1.516(3) . ? C9_1 C10_1 1.529(3) . ? C9_1 H9_1 1.00 . ? C10_1 N1_1 1.488(3) . ? C10_1 H10A_1 0.99 . ? C10_1 H10B_1 0.99 . ? N1_1 O6_1 1.211(3) . ? N1_1 O7_1 1.220(3) . ? C11_1 C16_1 1.385(3) . ? C11_1 C12_1 1.391(3) . ? C12_1 C13_1 1.370(4) . ? C12_1 H12_1 0.95 . ? C13_1 C14_1 1.378(4) . ? C13_1 H13_1 0.95 . ? C14_1 C15_1 1.373(4) . ? C14_1 H14_1 0.95 . ? C15_1 C16_1 1.379(4) . ? C15_1 H15_1 0.95 . ? C16_1 H16_1 0.95 . ? O1_2 C1_2 1.206(3) . ? O2_2 C1_2 1.333(3) . ? O2_2 C4_2 1.471(3) . ? O3_2 C2_2 1.415(3) . ? O3_2 C3_2 1.420(3) . ? O4_2 C3_2 1.407(3) . ? O4_2 C7_2 1.433(3) . ? O5_2 C4_2 1.390(3) . ? O5_2 C8_2 1.436(3) . ? C1_2 C2_2 1.513(3) . ? C2_2 C9_2 1.529(4) . ? C2_2 H2_2 1.00 . ? C3_2 C5_2 1.513(4) . ? C3_2 C4_2 1.534(3) . ? C4_2 C6_2 1.507(4) . ? C5_2 H5A_2 0.98 . ? C5_2 H5B_2 0.98 . ? C5_2 H5C_2 0.98 . ? C6_2 H6A_2 0.98 . ? C6_2 H6B_2 0.98 . ? C6_2 H6C_2 0.98 . ? C7_2 H7A_2 0.98 . ? C7_2 H7B_2 0.98 . ? C7_2 H7C_2 0.98 . ? C8_2 H8A_2 0.98 . ? C8_2 H8B_2 0.98 . ? C8_2 H8C_2 0.98 . ? C9_2 C11_2 1.512(4) . ? C9_2 C10_2 1.526(3) . ? C9_2 H9_2 1.00 . ? C10_2 N1_2 1.490(4) . ? C10_2 H10A_2 0.99 . ? C10_2 H10B_2 0.99 . ? N1_2 O6_2 1.169(3) . ? N1_2 O7_2 1.184(3) . ? C11_2 C16_2 1.384(4) . ? C11_2 C12_2 1.385(4) . ? C12_2 C13_2 1.382(5) . ? C12_2 H12_2 0.95 . ? C13_2 C14_2 1.382(5) . ? C13_2 H13_2 0.95 . ? C14_2 C15_2 1.366(5) . ? C14_2 H14_2 0.95 . ? C15_2 C16_2 1.373(4) . ? C15_2 H15_2 0.95 . ? C16_2 H16_2 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1_1 O2_1 C4_1 121.2(2) . . ? C2_1 O3_1 C3_1 113.7(2) . . ? C3_1 O4_1 C7_1 115.8(2) . . ? C4_1 O5_1 C8_1 116.2(2) . . ? O1_1 C1_1 O2_1 119.1(2) . . ? O1_1 C1_1 C2_1 120.5(2) . . ? O2_1 C1_1 C2_1 120.1(2) . . ? O3_1 C2_1 C1_1 115.0(2) . . ? O3_1 C2_1 C9_1 108.6(2) . . ? C1_1 C2_1 C9_1 111.9(2) . . ? O3_1 C2_1 H2_1 106.99(12) . . ? C1_1 C2_1 H2_1 106.99(13) . . ? C9_1 C2_1 H2_1 106.99(13) . . ? O4_1 C3_1 O3_1 110.6(2) . . ? O4_1 C3_1 C5_1 114.7(2) . . ? O3_1 C3_1 C5_1 105.6(2) . . ? O4_1 C3_1 C4_1 104.7(2) . . ? O3_1 C3_1 C4_1 108.7(2) . . ? C5_1 C3_1 C4_1 112.6(2) . . ? O5_1 C4_1 O2_1 107.7(2) . . ? O5_1 C4_1 C6_1 115.3(2) . . ? O2_1 C4_1 C6_1 105.1(2) . . ? O5_1 C4_1 C3_1 105.8(2) . . ? O2_1 C4_1 C3_1 109.0(2) . . ? C6_1 C4_1 C3_1 113.7(2) . . ? C3_1 C5_1 H5A_1 109.47(14) . . ? C3_1 C5_1 H5B_1 109.47(15) . . ? H5A_1 C5_1 H5B_1 109.5 . . ? C3_1 C5_1 H5C_1 109.47(15) . . ? H5A_1 C5_1 H5C_1 109.5 . . ? H5B_1 C5_1 H5C_1 109.5 . . ? C4_1 C6_1 H6A_1 109.47(14) . . ? C4_1 C6_1 H6B_1 109.5(2) . . ? H6A_1 C6_1 H6B_1 109.5 . . ? C4_1 C6_1 H6C_1 109.47(15) . . ? H6A_1 C6_1 H6C_1 109.5 . . ? H6B_1 C6_1 H6C_1 109.5 . . ? O4_1 C7_1 H7A_1 109.5(2) . . ? O4_1 C7_1 H7B_1 109.47(15) . . ? H7A_1 C7_1 H7B_1 109.5 . . ? O4_1 C7_1 H7C_1 109.5(2) . . ? H7A_1 C7_1 H7C_1 109.5 . . ? H7B_1 C7_1 H7C_1 109.5 . . ? O5_1 C8_1 H8A_1 109.5(2) . . ? O5_1 C8_1 H8B_1 109.5(2) . . ? H8A_1 C8_1 H8B_1 109.5 . . ? O5_1 C8_1 H8C_1 109.5(2) . . ? H8A_1 C8_1 H8C_1 109.5 . . ? H8B_1 C8_1 H8C_1 109.5 . . ? C11_1 C9_1 C2_1 113.9(2) . . ? C11_1 C9_1 C10_1 112.9(2) . . ? C2_1 C9_1 C10_1 107.7(2) . . ? C11_1 C9_1 H9_1 107.32(12) . . ? C2_1 C9_1 H9_1 107.32(12) . . ? C10_1 C9_1 H9_1 107.32(13) . . ? N1_1 C10_1 C9_1 108.9(2) . . ? N1_1 C10_1 H10A_1 109.91(14) . . ? C9_1 C10_1 H10A_1 109.91(13) . . ? N1_1 C10_1 H10B_1 109.91(14) . . ? C9_1 C10_1 H10B_1 109.91(13) . . ? H10A_1 C10_1 H10B_1 108.3 . . ? O6_1 N1_1 O7_1 123.3(3) . . ? O6_1 N1_1 C10_1 119.2(3) . . ? O7_1 N1_1 C10_1 117.5(2) . . ? C16_1 C11_1 C12_1 117.8(2) . . ? C16_1 C11_1 C9_1 120.2(2) . . ? C12_1 C11_1 C9_1 122.0(2) . . ? C13_1 C12_1 C11_1 121.2(2) . . ? C13_1 C12_1 H12_1 119.4(2) . . ? C11_1 C12_1 H12_1 119.41(15) . . ? C12_1 C13_1 C14_1 120.4(2) . . ? C12_1 C13_1 H13_1 119.8(2) . . ? C14_1 C13_1 H13_1 119.8(2) . . ? C15_1 C14_1 C13_1 119.3(3) . . ? C15_1 C14_1 H14_1 120.4(2) . . ? C13_1 C14_1 H14_1 120.4(2) . . ? C14_1 C15_1 C16_1 120.4(3) . . ? C14_1 C15_1 H15_1 119.8(2) . . ? C16_1 C15_1 H15_1 119.8(2) . . ? C15_1 C16_1 C11_1 121.0(2) . . ? C15_1 C16_1 H16_1 119.5(2) . . ? C11_1 C16_1 H16_1 119.5(2) . . ? C1_2 O2_2 C4_2 121.0(2) . . ? C2_2 O3_2 C3_2 113.7(2) . . ? C3_2 O4_2 C7_2 115.5(2) . . ? C4_2 O5_2 C8_2 117.1(2) . . ? O1_2 C1_2 O2_2 118.7(2) . . ? O1_2 C1_2 C2_2 120.6(2) . . ? O2_2 C1_2 C2_2 120.6(2) . . ? O3_2 C2_2 C1_2 115.3(2) . . ? O3_2 C2_2 C9_2 108.8(2) . . ? C1_2 C2_2 C9_2 111.1(2) . . ? O3_2 C2_2 H2_2 107.09(12) . . ? C1_2 C2_2 H2_2 107.09(14) . . ? C9_2 C2_2 H2_2 107.09(13) . . ? O4_2 C3_2 O3_2 110.0(2) . . ? O4_2 C3_2 C5_2 114.1(2) . . ? O3_2 C3_2 C5_2 106.4(2) . . ? O4_2 C3_2 C4_2 104.9(2) . . ? O3_2 C3_2 C4_2 108.4(2) . . ? C5_2 C3_2 C4_2 112.9(2) . . ? O5_2 C4_2 O2_2 108.7(2) . . ? O5_2 C4_2 C6_2 114.8(2) . . ? O2_2 C4_2 C6_2 104.4(2) . . ? O5_2 C4_2 C3_2 105.7(2) . . ? O2_2 C4_2 C3_2 108.7(2) . . ? C6_2 C4_2 C3_2 114.4(2) . . ? C3_2 C5_2 H5A_2 109.5(2) . . ? C3_2 C5_2 H5B_2 109.5(2) . . ? H5A_2 C5_2 H5B_2 109.5 . . ? C3_2 C5_2 H5C_2 109.5(2) . . ? H5A_2 C5_2 H5C_2 109.5 . . ? H5B_2 C5_2 H5C_2 109.5 . . ? C4_2 C6_2 H6A_2 109.47(15) . . ? C4_2 C6_2 H6B_2 109.5(2) . . ? H6A_2 C6_2 H6B_2 109.5 . . ? C4_2 C6_2 H6C_2 109.47(14) . . ? H6A_2 C6_2 H6C_2 109.5 . . ? H6B_2 C6_2 H6C_2 109.5 . . ? O4_2 C7_2 H7A_2 109.5(2) . . ? O4_2 C7_2 H7B_2 109.5(2) . . ? H7A_2 C7_2 H7B_2 109.5 . . ? O4_2 C7_2 H7C_2 109.5(2) . . ? H7A_2 C7_2 H7C_2 109.5 . . ? H7B_2 C7_2 H7C_2 109.5 . . ? O5_2 C8_2 H8A_2 109.5(2) . . ? O5_2 C8_2 H8B_2 109.47(15) . . ? H8A_2 C8_2 H8B_2 109.5 . . ? O5_2 C8_2 H8C_2 109.5(2) . . ? H8A_2 C8_2 H8C_2 109.5 . . ? H8B_2 C8_2 H8C_2 109.5 . . ? C11_2 C9_2 C10_2 112.9(2) . . ? C11_2 C9_2 C2_2 113.0(2) . . ? C10_2 C9_2 C2_2 108.6(2) . . ? C11_2 C9_2 H9_2 107.36(14) . . ? C10_2 C9_2 H9_2 107.36(14) . . ? C2_2 C9_2 H9_2 107.36(13) . . ? N1_2 C10_2 C9_2 110.3(2) . . ? N1_2 C10_2 H10A_2 109.60(15) . . ? C9_2 C10_2 H10A_2 109.60(14) . . ? N1_2 C10_2 H10B_2 109.60(15) . . ? C9_2 C10_2 H10B_2 109.60(14) . . ? H10A_2 C10_2 H10B_2 108.1 . . ? O6_2 N1_2 O7_2 121.6(3) . . ? O6_2 N1_2 C10_2 118.6(3) . . ? O7_2 N1_2 C10_2 119.7(3) . . ? C16_2 C11_2 C12_2 118.0(3) . . ? C16_2 C11_2 C9_2 122.1(2) . . ? C12_2 C11_2 C9_2 119.8(2) . . ? C13_2 C12_2 C11_2 120.9(3) . . ? C13_2 C12_2 H12_2 119.6(2) . . ? C11_2 C12_2 H12_2 119.6(2) . . ? C12_2 C13_2 C14_2 120.2(3) . . ? C12_2 C13_2 H13_2 119.9(2) . . ? C14_2 C13_2 H13_2 119.9(2) . . ? C15_2 C14_2 C13_2 118.9(3) . . ? C15_2 C14_2 H14_2 120.6(2) . . ? C13_2 C14_2 H14_2 120.6(2) . . ? C14_2 C15_2 C16_2 121.2(3) . . ? C14_2 C15_2 H15_2 119.4(2) . . ? C16_2 C15_2 H15_2 119.4(2) . . ? C15_2 C16_2 C11_2 120.8(3) . . ? C15_2 C16_2 H16_2 119.6(2) . . ? C11_2 C16_2 H16_2 119.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4_1 O2_1 C1_1 O1_1 176.1(2) . . . . ? C4_1 O2_1 C1_1 C2_1 -9.2(3) . . . . ? C3_1 O3_1 C2_1 C1_1 -39.3(3) . . . . ? C3_1 O3_1 C2_1 C9_1 -165.4(2) . . . . ? O1_1 C1_1 C2_1 O3_1 -174.3(2) . . . . ? O2_1 C1_1 C2_1 O3_1 11.1(3) . . . . ? O1_1 C1_1 C2_1 C9_1 -49.8(3) . . . . ? O2_1 C1_1 C2_1 C9_1 135.6(2) . . . . ? C7_1 O4_1 C3_1 O3_1 -67.2(3) . . . . ? C7_1 O4_1 C3_1 C5_1 52.1(3) . . . . ? C7_1 O4_1 C3_1 C4_1 176.0(2) . . . . ? C2_1 O3_1 C3_1 O4_1 -51.5(2) . . . . ? C2_1 O3_1 C3_1 C5_1 -176.1(2) . . . . ? C2_1 O3_1 C3_1 C4_1 62.9(2) . . . . ? C8_1 O5_1 C4_1 O2_1 -62.9(3) . . . . ? C8_1 O5_1 C4_1 C6_1 54.0(3) . . . . ? C8_1 O5_1 C4_1 C3_1 -179.4(3) . . . . ? C1_1 O2_1 C4_1 O5_1 -82.7(3) . . . . ? C1_1 O2_1 C4_1 C6_1 153.8(2) . . . . ? C1_1 O2_1 C4_1 C3_1 31.6(3) . . . . ? O4_1 C3_1 C4_1 O5_1 176.6(2) . . . . ? O3_1 C3_1 C4_1 O5_1 58.4(2) . . . . ? C5_1 C3_1 C4_1 O5_1 -58.2(3) . . . . ? O4_1 C3_1 C4_1 O2_1 61.1(2) . . . . ? O3_1 C3_1 C4_1 O2_1 -57.1(3) . . . . ? C5_1 C3_1 C4_1 O2_1 -173.7(2) . . . . ? O4_1 C3_1 C4_1 C6_1 -55.8(3) . . . . ? O3_1 C3_1 C4_1 C6_1 -174.0(2) . . . . ? C5_1 C3_1 C4_1 C6_1 69.4(3) . . . . ? O3_1 C2_1 C9_1 C11_1 56.6(2) . . . . ? C1_1 C2_1 C9_1 C11_1 -71.3(3) . . . . ? O3_1 C2_1 C9_1 C10_1 -69.4(2) . . . . ? C1_1 C2_1 C9_1 C10_1 162.6(2) . . . . ? C11_1 C9_1 C10_1 N1_1 62.2(3) . . . . ? C2_1 C9_1 C10_1 N1_1 -171.1(2) . . . . ? C9_1 C10_1 N1_1 O6_1 -116.1(3) . . . . ? C9_1 C10_1 N1_1 O7_1 64.1(3) . . . . ? C2_1 C9_1 C11_1 C16_1 101.3(3) . . . . ? C10_1 C9_1 C11_1 C16_1 -135.4(2) . . . . ? C2_1 C9_1 C11_1 C12_1 -81.1(3) . . . . ? C10_1 C9_1 C11_1 C12_1 42.2(3) . . . . ? C16_1 C11_1 C12_1 C13_1 0.8(4) . . . . ? C9_1 C11_1 C12_1 C13_1 -176.8(2) . . . . ? C11_1 C12_1 C13_1 C14_1 -1.1(4) . . . . ? C12_1 C13_1 C14_1 C15_1 0.0(4) . . . . ? C13_1 C14_1 C15_1 C16_1 1.5(4) . . . . ? C14_1 C15_1 C16_1 C11_1 -1.8(4) . . . . ? C12_1 C11_1 C16_1 C15_1 0.7(4) . . . . ? C9_1 C11_1 C16_1 C15_1 178.3(2) . . . . ? C4_2 O2_2 C1_2 O1_2 -179.4(2) . . . . ? C4_2 O2_2 C1_2 C2_2 -2.0(4) . . . . ? C3_2 O3_2 C2_2 C1_2 -34.1(3) . . . . ? C3_2 O3_2 C2_2 C9_2 -159.7(2) . . . . ? O1_2 C1_2 C2_2 O3_2 179.7(2) . . . . ? O2_2 C1_2 C2_2 O3_2 2.4(4) . . . . ? O1_2 C1_2 C2_2 C9_2 -55.9(3) . . . . ? O2_2 C1_2 C2_2 C9_2 126.7(3) . . . . ? C7_2 O4_2 C3_2 O3_2 -63.5(3) . . . . ? C7_2 O4_2 C3_2 C5_2 56.0(3) . . . . ? C7_2 O4_2 C3_2 C4_2 -179.9(2) . . . . ? C2_2 O3_2 C3_2 O4_2 -51.5(3) . . . . ? C2_2 O3_2 C3_2 C5_2 -175.5(2) . . . . ? C2_2 O3_2 C3_2 C4_2 62.8(3) . . . . ? C8_2 O5_2 C4_2 O2_2 -52.8(3) . . . . ? C8_2 O5_2 C4_2 C6_2 63.7(3) . . . . ? C8_2 O5_2 C4_2 C3_2 -169.3(2) . . . . ? C1_2 O2_2 C4_2 O5_2 -85.0(3) . . . . ? C1_2 O2_2 C4_2 C6_2 152.0(2) . . . . ? C1_2 O2_2 C4_2 C3_2 29.6(3) . . . . ? O4_2 C3_2 C4_2 O5_2 175.1(2) . . . . ? O3_2 C3_2 C4_2 O5_2 57.6(2) . . . . ? C5_2 C3_2 C4_2 O5_2 -60.0(3) . . . . ? O4_2 C3_2 C4_2 O2_2 58.6(3) . . . . ? O3_2 C3_2 C4_2 O2_2 -58.9(3) . . . . ? C5_2 C3_2 C4_2 O2_2 -176.6(2) . . . . ? O4_2 C3_2 C4_2 C6_2 -57.6(3) . . . . ? O3_2 C3_2 C4_2 C6_2 -175.1(2) . . . . ? C5_2 C3_2 C4_2 C6_2 67.3(3) . . . . ? O3_2 C2_2 C9_2 C11_2 61.8(2) . . . . ? C1_2 C2_2 C9_2 C11_2 -66.1(3) . . . . ? O3_2 C2_2 C9_2 C10_2 -64.2(2) . . . . ? C1_2 C2_2 C9_2 C10_2 167.8(2) . . . . ? C11_2 C9_2 C10_2 N1_2 62.5(3) . . . . ? C2_2 C9_2 C10_2 N1_2 -171.4(2) . . . . ? C9_2 C10_2 N1_2 O6_2 53.8(4) . . . . ? C9_2 C10_2 N1_2 O7_2 -130.5(3) . . . . ? C10_2 C9_2 C11_2 C16_2 44.0(3) . . . . ? C2_2 C9_2 C11_2 C16_2 -79.7(3) . . . . ? C10_2 C9_2 C11_2 C12_2 -137.2(3) . . . . ? C2_2 C9_2 C11_2 C12_2 99.1(3) . . . . ? C16_2 C11_2 C12_2 C13_2 -0.4(4) . . . . ? C9_2 C11_2 C12_2 C13_2 -179.2(3) . . . . ? C11_2 C12_2 C13_2 C14_2 -1.3(5) . . . . ? C12_2 C13_2 C14_2 C15_2 1.7(5) . . . . ? C13_2 C14_2 C15_2 C16_2 -0.4(5) . . . . ? C14_2 C15_2 C16_2 C11_2 -1.3(5) . . . . ? C12_2 C11_2 C16_2 C15_2 1.7(4) . . . . ? C9_2 C11_2 C16_2 C15_2 -179.5(3) . . . . ? _refine_diff_density_max 0.280 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.051 data_sl0031 _database_code_depnum_ccdc_archive 'CCDC 283221' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H23 N O7' _chemical_formula_weight 317.33 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.2904(8) _cell_length_b 10.4950(6) _cell_length_c 11.2184(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.840(3) _cell_angle_gamma 90.00 _cell_volume 1592.37(14) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 11623 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method ? _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.234 _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13927 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3625 _reflns_number_observed 2547 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.3213P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3619 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_obs 0.0498 _refine_ls_wR_factor_all 0.1870 _refine_ls_wR_factor_obs 0.1305 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.119 _refine_ls_restrained_S_all 1.331 _refine_ls_restrained_S_obs 1.119 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.91357(13) -0.1244(2) 1.0305(2) 0.1004(8) Uani 1 d . . O2 O 0.77159(9) -0.21983(12) 0.96681(10) 0.0423(3) Uani 1 d . . O3 O 0.69314(8) -0.03117(10) 0.78830(9) 0.0329(3) Uani 1 d . . O4 O 0.62210(9) -0.04181(11) 0.94766(11) 0.0414(3) Uani 1 d . . O5 O 0.67799(9) -0.28925(12) 0.76830(10) 0.0430(3) Uani 1 d . . O6 O 0.67931(14) 0.2544(2) 0.7232(2) 0.0810(6) Uani 1 d . . O7 O 0.69927(11) 0.1417(2) 0.57343(14) 0.0635(4) Uani 1 d . . N1 N 0.73030(13) 0.18934(15) 0.6778(2) 0.0498(4) Uani 1 d . . C1 C 0.82954(15) -0.1223(2) 0.9621(2) 0.0508(5) Uani 1 d . . C2 C 0.78760(12) -0.0092(2) 0.87732(15) 0.0376(4) Uani 1 d . . H2 H 0.78129(12) 0.0623(2) 0.93176(15) 0.045 Uiso 1 calc R . C3 C 0.62740(12) -0.0994(2) 0.83672(14) 0.0322(4) Uani 1 d . . C4 C 0.67150(12) -0.2321(2) 0.87777(14) 0.0337(4) Uani 1 d . . C5 C 0.53014(12) -0.1045(2) 0.7313(2) 0.0390(4) Uani 1 d . . H5A H 0.5102(4) -0.0189(2) 0.7012(8) 0.058 Uiso 1 calc R . H5B H 0.4802(2) -0.1421(10) 0.7621(3) 0.058 Uiso 1 calc R . H5C H 0.5374(3) -0.1559(9) 0.6630(5) 0.058 Uiso 1 calc R . C6 C 0.61628(14) -0.3082(2) 0.9475(2) 0.0431(4) Uani 1 d . . H6A H 0.6447(6) -0.3928(4) 0.9648(10) 0.065 Uiso 1 calc R . H6B H 0.5473(2) -0.3148(10) 0.8963(5) 0.065 Uiso 1 calc R . H6C H 0.6213(8) -0.2660(6) 1.0262(6) 0.065 Uiso 1 calc R . C7 C 0.5783(2) 0.0825(2) 0.9319(2) 0.0559(5) Uani 1 d . . H7A H 0.5881(10) 0.1205(6) 1.0139(2) 0.084 Uiso 1 calc R . H7B H 0.5080(3) 0.0755(2) 0.8869(12) 0.084 Uiso 1 calc R . H7C H 0.6090(8) 0.1356(5) 0.8842(12) 0.084 Uiso 1 calc R . C8 C 0.7255(2) -0.4106(2) 0.7806(2) 0.0593(6) Uani 1 d . . H8A H 0.7269(10) -0.4386(7) 0.6988(3) 0.089 Uiso 1 calc R . H8B H 0.6893(7) -0.4719(4) 0.8134(14) 0.089 Uiso 1 calc R . H8C H 0.7926(4) -0.4035(4) 0.8380(12) 0.089 Uiso 1 calc R . C9 C 0.85740(12) 0.0334(2) 0.80671(15) 0.0356(4) Uani 1 d . . H9 H 0.92420(12) 0.0349(2) 0.87024(15) 0.043 Uiso 1 calc R . C10 C 0.83720(14) 0.1702(2) 0.7572(2) 0.0414(4) Uani 1 d . . H10 H 0.85096(14) 0.2274(2) 0.8311(2) 0.050 Uiso 1 calc R . C11 C 0.9053(2) 0.2097(2) 0.6830(2) 0.0516(5) Uani 1 d . . H11A H 0.8811(2) 0.2902(2) 0.6397(2) 0.062 Uiso 1 calc R . H11B H 0.9715(2) 0.2253(2) 0.7425(2) 0.062 Uiso 1 calc R . C12 C 0.9133(2) 0.1132(2) 0.5866(2) 0.0579(6) Uani 1 d . . H12A H 0.9648(2) 0.1403(2) 0.5517(2) 0.069 Uiso 1 calc R . H12B H 0.8505(2) 0.1095(2) 0.5174(2) 0.069 Uiso 1 calc R . C13 C 0.9383(2) -0.0180(2) 0.6443(2) 0.0604(6) Uani 1 d . . H13A H 1.0044(2) -0.0164(2) 0.7072(2) 0.072 Uiso 1 calc R . H13B H 0.9392(2) -0.0791(2) 0.5786(2) 0.072 Uiso 1 calc R . C14 C 0.86333(14) -0.0614(2) 0.7067(2) 0.0433(4) Uani 1 d . . H14A H 0.79810(14) -0.0697(2) 0.6426(2) 0.052 Uiso 1 calc R . H14B H 0.88261(14) -0.1451(2) 0.7455(2) 0.052 Uiso 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 0.0519(10) 0.125(2) 0.0871(12) 0.0632(11) -0.0283(9) -0.0397(10) O2 0.0349(7) 0.0463(7) 0.0381(6) 0.0117(5) 0.0012(5) -0.0063(5) O3 0.0285(6) 0.0371(6) 0.0327(6) 0.0043(4) 0.0095(5) -0.0045(5) O4 0.0524(8) 0.0377(7) 0.0407(6) -0.0062(5) 0.0240(6) -0.0050(6) O5 0.0530(8) 0.0399(7) 0.0345(6) -0.0005(5) 0.0121(6) 0.0127(6) O6 0.0912(13) 0.0608(10) 0.1151(14) 0.0200(9) 0.0669(12) 0.0313(9) O7 0.0521(9) 0.0734(11) 0.0557(9) 0.0090(8) 0.0046(7) 0.0064(8) N1 0.0544(10) 0.0363(9) 0.0667(11) 0.0141(8) 0.0304(9) 0.0104(8) C1 0.0410(11) 0.0642(13) 0.0378(9) 0.0152(9) -0.0004(8) -0.0168(9) C2 0.0347(9) 0.0429(10) 0.0319(8) 0.0009(7) 0.0063(7) -0.0102(7) C3 0.0317(8) 0.0346(9) 0.0326(8) -0.0006(6) 0.0139(6) -0.0037(7) C4 0.0323(9) 0.0365(9) 0.0291(8) 0.0003(6) 0.0057(6) -0.0027(7) C5 0.0300(9) 0.0405(9) 0.0457(9) 0.0041(7) 0.0111(7) 0.0003(7) C6 0.0477(11) 0.0386(10) 0.0423(9) 0.0036(7) 0.0134(8) -0.0102(8) C7 0.0685(14) 0.0403(11) 0.0715(13) -0.0098(9) 0.0402(11) -0.0010(10) C8 0.0696(15) 0.0453(12) 0.0613(12) -0.0024(9) 0.0188(11) 0.0201(10) C9 0.0290(9) 0.0395(9) 0.0344(8) 0.0040(7) 0.0048(7) -0.0063(7) C10 0.0477(11) 0.0358(9) 0.0411(9) -0.0031(7) 0.0149(8) -0.0090(8) C11 0.0509(12) 0.0496(11) 0.0553(11) 0.0114(9) 0.0188(9) -0.0126(9) C12 0.0552(13) 0.0725(15) 0.0564(12) 0.0102(11) 0.0325(10) -0.0038(11) C13 0.0517(13) 0.0687(15) 0.0726(14) 0.0017(11) 0.0364(11) 0.0075(11) C14 0.0382(10) 0.0377(10) 0.0568(11) 0.0021(8) 0.0193(8) 0.0040(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 C1 1.199(2) . ? O2 C1 1.328(2) . ? O2 C4 1.462(2) . ? O3 C2 1.415(2) . ? O3 C3 1.421(2) . ? O4 C3 1.408(2) . ? O4 C7 1.433(2) . ? O5 C4 1.396(2) . ? O5 C8 1.429(2) . ? O6 N1 1.223(2) . ? O7 N1 1.217(2) . ? N1 C10 1.513(3) . ? C1 C2 1.518(3) . ? C2 C9 1.527(2) . ? C2 H2 0.99 . ? C3 C5 1.507(2) . ? C3 C4 1.536(2) . ? C4 C6 1.507(2) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C5 H5C 0.97 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C6 H6C 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C7 H7C 0.97 . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C8 H8C 0.97 . ? C9 C14 1.522(3) . ? C9 C10 1.533(2) . ? C9 H9 0.99 . ? C10 C11 1.528(3) . ? C10 H10 0.99 . ? C11 C12 1.512(3) . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C12 C13 1.515(3) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C13 C14 1.526(3) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 121.70(13) . . ? C2 O3 C3 114.20(11) . . ? C3 O4 C7 115.34(14) . . ? C4 O5 C8 117.53(14) . . ? O7 N1 O6 123.3(2) . . ? O7 N1 C10 119.8(2) . . ? O6 N1 C10 116.9(2) . . ? O1 C1 O2 118.0(2) . . ? O1 C1 C2 121.8(2) . . ? O2 C1 C2 120.2(2) . . ? O3 C2 C1 114.12(14) . . ? O3 C2 C9 108.39(12) . . ? C1 C2 C9 111.2(2) . . ? O3 C2 H2 107.62(9) . . ? C1 C2 H2 107.62(10) . . ? C9 C2 H2 107.62(9) . . ? O4 C3 O3 110.63(12) . . ? O4 C3 C5 114.18(14) . . ? O3 C3 C5 105.91(12) . . ? O4 C3 C4 104.97(12) . . ? O3 C3 C4 108.27(13) . . ? C5 C3 C4 112.83(13) . . ? O5 C4 O2 108.09(13) . . ? O5 C4 C6 115.05(14) . . ? O2 C4 C6 104.64(12) . . ? O5 C4 C3 105.25(12) . . ? O2 C4 C3 109.94(13) . . ? C6 C4 C3 113.77(14) . . ? C3 C5 H5A 109.47(9) . . ? C3 C5 H5B 109.47(9) . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.47(9) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.47(10) . . ? C4 C6 H6B 109.47(9) . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.47(9) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.47(10) . . ? O4 C7 H7B 109.47(10) . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.47(10) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.47(10) . . ? O5 C8 H8B 109.47(12) . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.47(11) . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C2 113.08(14) . . ? C14 C9 C10 113.20(14) . . ? C2 C9 C10 112.59(15) . . ? C14 C9 H9 105.71(9) . . ? C2 C9 H9 105.71(8) . . ? C10 C9 H9 105.71(9) . . ? N1 C10 C11 110.02(14) . . ? N1 C10 C9 111.95(14) . . ? C11 C10 C9 111.9(2) . . ? N1 C10 H10 107.59(9) . . ? C11 C10 H10 107.59(10) . . ? C9 C10 H10 107.59(9) . . ? C12 C11 C10 114.7(2) . . ? C12 C11 H11A 108.60(11) . . ? C10 C11 H11A 108.60(11) . . ? C12 C11 H11B 108.60(12) . . ? C10 C11 H11B 108.60(10) . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 111.4(2) . . ? C11 C12 H12A 109.35(11) . . ? C13 C12 H12A 109.35(11) . . ? C11 C12 H12B 109.35(12) . . ? C13 C12 H12B 109.35(13) . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 111.4(2) . . ? C12 C13 H13A 109.36(12) . . ? C14 C13 H13A 109.36(12) . . ? C12 C13 H13B 109.36(12) . . ? C14 C13 H13B 109.36(12) . . ? H13A C13 H13B 108.0 . . ? C9 C14 C13 110.9(2) . . ? C9 C14 H14A 109.45(9) . . ? C13 C14 H14A 109.45(12) . . ? C9 C14 H14B 109.45(9) . . ? C13 C14 H14B 109.45(11) . . ? H14A C14 H14B 108.0 . . ? 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 C4 O2 C1 O1 -173.4(2) . . . . ? C4 O2 C1 C2 10.0(3) . . . . ? C3 O3 C2 C1 41.3(2) . . . . ? C3 O3 C2 C9 165.88(13) . . . . ? O1 C1 C2 O3 170.0(2) . . . . ? O2 C1 C2 O3 -13.5(3) . . . . ? O1 C1 C2 C9 47.0(3) . . . . ? O2 C1 C2 C9 -136.5(2) . . . . ? C7 O4 C3 O3 66.3(2) . . . . ? C7 O4 C3 C5 -53.1(2) . . . . ? C7 O4 C3 C4 -177.15(14) . . . . ? C2 O3 C3 O4 51.9(2) . . . . ? C2 O3 C3 C5 176.10(13) . . . . ? C2 O3 C3 C4 -62.6(2) . . . . ? C8 O5 C4 O2 56.9(2) . . . . ? C8 O5 C4 C6 -59.7(2) . . . . ? C8 O5 C4 C3 174.3(2) . . . . ? C1 O2 C4 O5 83.8(2) . . . . ? C1 O2 C4 C6 -153.1(2) . . . . ? C1 O2 C4 C3 -30.5(2) . . . . ? O4 C3 C4 O5 -179.35(12) . . . . ? O3 C3 C4 O5 -61.2(2) . . . . ? C5 C3 C4 O5 55.7(2) . . . . ? O4 C3 C4 O2 -63.2(2) . . . . ? O3 C3 C4 O2 55.0(2) . . . . ? C5 C3 C4 O2 171.91(12) . . . . ? O4 C3 C4 C6 53.8(2) . . . . ? O3 C3 C4 C6 172.00(12) . . . . ? C5 C3 C4 C6 -71.1(2) . . . . ? O3 C2 C9 C14 -56.4(2) . . . . ? C1 C2 C9 C14 69.8(2) . . . . ? O3 C2 C9 C10 73.5(2) . . . . ? C1 C2 C9 C10 -160.30(15) . . . . ? O7 N1 C10 C11 53.5(2) . . . . ? O6 N1 C10 C11 -125.8(2) . . . . ? O7 N1 C10 C9 -71.6(2) . . . . ? O6 N1 C10 C9 109.1(2) . . . . ? C14 C9 C10 N1 75.8(2) . . . . ? C2 C9 C10 N1 -54.0(2) . . . . ? C14 C9 C10 C11 -48.2(2) . . . . ? C2 C9 C10 C11 -178.02(14) . . . . ? N1 C10 C11 C12 -77.9(2) . . . . ? C9 C10 C11 C12 47.2(2) . . . . ? C10 C11 C12 C13 -51.4(2) . . . . ? C11 C12 C13 C14 55.8(2) . . . . ? C2 C9 C14 C13 -176.75(15) . . . . ? C10 C9 C14 C13 53.7(2) . . . . ? C12 C13 C14 C9 -57.2(2) . . . . ? _refine_diff_density_max 0.298 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.071 data_sl0325 _database_code_depnum_ccdc_archive 'CCDC 283222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H28 O6' _chemical_formula_sum 'C17 H28 O6' _chemical_formula_weight 328.39 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.9383(2) _cell_length_b 14.4423(3) _cell_length_c 15.4979(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1776.79(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9661 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14970 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4057 _reflns_number_gt 3405 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.2108P] 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 -0.5(10) _refine_ls_number_reflns 4057 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.32136(16) 0.61136(9) 0.49684(11) 0.0569(4) Uani 1 1 d . . . O2 O 0.51339(14) 0.40674(7) 0.41136(8) 0.0345(3) Uani 1 1 d . . . O3 O 0.22220(14) 0.51529(8) 0.39951(9) 0.0374(3) Uani 1 1 d . . . O4 O 0.27489(16) 0.35202(8) 0.48255(9) 0.0413(3) Uani 1 1 d . . . O5 O 0.31905(16) 0.44664(10) 0.27359(9) 0.0455(3) Uani 1 1 d . . . O6 O 0.86422(19) 0.61827(11) 0.24665(9) 0.0538(4) Uani 1 1 d . . . C1 C 0.6624(2) 0.54720(11) 0.43327(11) 0.0304(3) Uani 1 1 d . . . H1 H 0.7573 0.5021 0.4272 0.037 Uiso 1 1 calc R . . C2 C 0.5076(2) 0.48993(10) 0.46074(11) 0.0323(3) Uani 1 1 d . . . H2 H 0.5228 0.4727 0.5228 0.039 Uiso 1 1 calc R . . C3 C 0.3445(2) 0.54335(11) 0.45343(12) 0.0372(4) Uani 1 1 d . . . C4 C 0.2379(2) 0.42870(12) 0.35126(12) 0.0363(4) Uani 1 1 d . . . C5 C 0.3545(2) 0.36329(11) 0.40148(12) 0.0355(4) Uani 1 1 d . . . C6 C 0.3883(3) 0.27307(13) 0.35459(16) 0.0512(5) Uani 1 1 d . . . H6A H 0.4730 0.2373 0.3864 0.077 Uiso 1 1 calc R . . H6B H 0.4301 0.2863 0.2964 0.077 Uiso 1 1 calc R . . H6C H 0.2838 0.2372 0.3507 0.077 Uiso 1 1 calc R . . C7 C 0.0585(2) 0.39388(15) 0.34214(15) 0.0475(5) Uani 1 1 d . . . H7A H -0.0108 0.4418 0.3148 0.071 Uiso 1 1 calc R . . H7B H 0.0128 0.3795 0.3993 0.071 Uiso 1 1 calc R . . H7C H 0.0575 0.3379 0.3064 0.071 Uiso 1 1 calc R . . C8 C 0.3580(3) 0.29099(15) 0.54171(15) 0.0570(6) Uani 1 1 d . . . H8A H 0.3181 0.3034 0.6004 0.086 Uiso 1 1 calc R . . H8B H 0.4799 0.3012 0.5389 0.086 Uiso 1 1 calc R . . H8C H 0.3328 0.2267 0.5263 0.086 Uiso 1 1 calc R . . C9 C 0.2306(3) 0.5045(2) 0.21374(16) 0.0726(7) Uani 1 1 d . . . H9A H 0.3080 0.5249 0.1683 0.109 Uiso 1 1 calc R . . H9B H 0.1855 0.5586 0.2441 0.109 Uiso 1 1 calc R . . H9C H 0.1377 0.4694 0.1879 0.109 Uiso 1 1 calc R . . C10 C 0.6351(2) 0.58905(12) 0.34306(12) 0.0395(4) Uani 1 1 d . . . H10A H 0.6064 0.5392 0.3017 0.047 Uiso 1 1 calc R . . H10B H 0.5398 0.6333 0.3449 0.047 Uiso 1 1 calc R . . C11 C 0.7922(2) 0.63838(12) 0.31332(13) 0.0409(4) Uani 1 1 d . . . C12 C 0.8539(3) 0.71043(13) 0.37461(13) 0.0482(5) Uani 1 1 d . . . H12A H 0.7704 0.7612 0.3786 0.058 Uiso 1 1 calc R . . H12B H 0.9611 0.7368 0.3531 0.058 Uiso 1 1 calc R . . C13 C 0.8812(2) 0.66783(11) 0.46374(13) 0.0390(4) Uani 1 1 d . . . H13A H 0.9164 0.7170 0.5044 0.047 Uiso 1 1 calc R . . H13B H 0.9735 0.6218 0.4603 0.047 Uiso 1 1 calc R . . C14 C 0.7220(2) 0.62026(11) 0.49881(12) 0.0340(4) Uani 1 1 d . . . H14 H 0.6318 0.6683 0.5039 0.041 Uiso 1 1 calc R . . C18 C 0.7521(2) 0.57872(14) 0.58973(12) 0.0438(4) Uani 1 1 d . . . H18 H 0.6399 0.5587 0.6123 0.053 Uiso 1 1 calc R . . C19 C 0.8650(3) 0.49304(15) 0.58856(15) 0.0570(5) Uani 1 1 d . . . H19A H 0.8834 0.4715 0.6478 0.086 Uiso 1 1 calc R . . H19B H 0.9736 0.5087 0.5622 0.086 Uiso 1 1 calc R . . H19C H 0.8106 0.4440 0.5549 0.086 Uiso 1 1 calc R . . C20 C 0.8215(3) 0.65103(19) 0.65305(15) 0.0655(7) Uani 1 1 d . . . H20A H 0.8103 0.6279 0.7122 0.098 Uiso 1 1 calc R . . H20B H 0.7580 0.7088 0.6470 0.098 Uiso 1 1 calc R . . H20C H 0.9407 0.6625 0.6404 0.098 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 0.0364(7) 0.0488(8) 0.0857(11) -0.0325(8) 0.0054(8) 0.0017(6) O2 0.0270(5) 0.0301(5) 0.0463(7) -0.0094(5) -0.0005(5) -0.0004(5) O3 0.0309(6) 0.0336(6) 0.0477(7) -0.0059(5) -0.0009(5) 0.0030(5) O4 0.0381(6) 0.0385(6) 0.0473(7) 0.0032(5) 0.0003(6) -0.0031(5) O5 0.0339(7) 0.0659(8) 0.0369(7) -0.0026(6) 0.0006(5) 0.0051(6) O6 0.0459(8) 0.0712(9) 0.0443(8) 0.0098(7) 0.0039(7) 0.0038(7) C1 0.0256(7) 0.0308(7) 0.0349(9) -0.0019(6) -0.0002(7) -0.0001(6) C2 0.0299(8) 0.0310(8) 0.0358(9) -0.0054(7) 0.0004(7) -0.0031(7) C3 0.0292(8) 0.0338(8) 0.0484(11) -0.0088(7) 0.0071(8) -0.0023(7) C4 0.0303(8) 0.0392(9) 0.0394(10) -0.0103(7) 0.0013(7) -0.0006(7) C5 0.0289(8) 0.0332(8) 0.0443(10) -0.0076(7) 0.0007(8) -0.0037(6) C6 0.0441(10) 0.0362(9) 0.0732(15) -0.0175(9) -0.0001(10) -0.0038(8) C7 0.0293(9) 0.0548(12) 0.0584(13) -0.0093(10) -0.0043(8) -0.0035(8) C8 0.0555(13) 0.0508(11) 0.0648(14) 0.0167(10) -0.0061(11) -0.0040(10) C9 0.0512(13) 0.117(2) 0.0501(14) 0.0211(13) 0.0018(11) 0.0132(14) C10 0.0373(9) 0.0427(9) 0.0386(10) 0.0014(8) -0.0048(8) -0.0017(8) C11 0.0378(9) 0.0416(9) 0.0434(11) 0.0135(8) -0.0026(8) 0.0025(8) C12 0.0472(11) 0.0398(9) 0.0576(13) 0.0104(9) -0.0005(10) -0.0101(8) C13 0.0329(9) 0.0339(8) 0.0502(11) -0.0013(7) -0.0047(8) -0.0052(7) C14 0.0266(8) 0.0329(8) 0.0425(10) -0.0065(7) -0.0022(7) 0.0009(6) C18 0.0355(9) 0.0614(11) 0.0346(9) -0.0041(8) -0.0009(8) -0.0098(8) C19 0.0570(13) 0.0675(13) 0.0466(11) 0.0159(10) -0.0060(11) 0.0020(11) C20 0.0552(13) 0.0917(17) 0.0495(13) -0.0209(12) -0.0053(11) -0.0179(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 C3 1.205(2) . ? O2 C5 1.417(2) . ? O2 C2 1.4252(18) . ? O3 C3 1.343(2) . ? O3 C4 1.462(2) . ? O4 C5 1.416(2) . ? O4 C8 1.433(2) . ? O5 C4 1.390(2) . ? O5 C9 1.432(3) . ? O6 C11 1.216(2) . ? C1 C10 1.539(2) . ? C1 C14 1.539(2) . ? C1 C2 1.541(2) . ? C1 H1 1.0000 . ? C2 C3 1.512(2) . ? C2 H2 1.0000 . ? C4 C7 1.517(2) . ? C4 C5 1.535(3) . ? C5 C6 1.516(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.509(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.492(3) . ? C12 C13 1.528(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.538(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C18 1.550(3) . ? C14 H14 1.0000 . ? C18 C19 1.528(3) . ? C18 C20 1.535(3) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C5 O2 C2 113.75(12) . . ? C3 O3 C4 120.96(13) . . ? C5 O4 C8 115.66(15) . . ? C4 O5 C9 116.26(15) . . ? C10 C1 C14 111.94(13) . . ? C10 C1 C2 110.44(14) . . ? C14 C1 C2 115.51(14) . . ? C10 C1 H1 106.1 . . ? C14 C1 H1 106.1 . . ? C2 C1 H1 106.1 . . ? O2 C2 C3 114.68(14) . . ? O2 C2 C1 106.16(13) . . ? C3 C2 C1 112.86(13) . . ? O2 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C1 C2 H2 107.6 . . ? O1 C3 O3 118.91(16) . . ? O1 C3 C2 120.31(17) . . ? O3 C3 C2 120.77(14) . . ? O5 C4 O3 108.85(14) . . ? O5 C4 C7 114.60(17) . . ? O3 C4 C7 104.54(14) . . ? O5 C4 C5 105.93(13) . . ? O3 C4 C5 108.58(13) . . ? C7 C4 C5 114.18(15) . . ? O4 C5 O2 110.63(14) . . ? O4 C5 C6 113.93(15) . . ? O2 C5 C6 105.96(14) . . ? O4 C5 C4 104.56(13) . . ? O2 C5 C4 108.60(13) . . ? C6 C5 C4 113.14(16) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C1 110.26(14) . . ? C11 C10 H10A 109.6 . . ? C1 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C1 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O6 C11 C12 123.60(18) . . ? O6 C11 C10 122.38(17) . . ? C12 C11 C10 113.97(17) . . ? C11 C12 C13 109.97(14) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C12 C13 C14 112.50(15) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C1 109.01(14) . . ? C13 C14 C18 111.55(14) . . ? C1 C14 C18 112.45(13) . . ? C13 C14 H14 107.9 . . ? C1 C14 H14 107.9 . . ? C18 C14 H14 107.9 . . ? C19 C18 C20 110.37(18) . . ? C19 C18 C14 113.15(16) . . ? C20 C18 C14 111.91(17) . . ? C19 C18 H18 107.0 . . ? C20 C18 H18 107.0 . . ? C14 C18 H18 107.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C5 O2 C2 C3 -31.03(19) . . . . ? C5 O2 C2 C1 -156.36(14) . . . . ? C10 C1 C2 O2 73.91(16) . . . . ? C14 C1 C2 O2 -157.79(13) . . . . ? C10 C1 C2 C3 -52.53(18) . . . . ? C14 C1 C2 C3 75.76(18) . . . . ? C4 O3 C3 O1 -174.46(17) . . . . ? C4 O3 C3 C2 4.7(2) . . . . ? O2 C2 C3 O1 175.00(17) . . . . ? C1 C2 C3 O1 -63.3(2) . . . . ? O2 C2 C3 O3 -4.1(2) . . . . ? C1 C2 C3 O3 117.64(17) . . . . ? C9 O5 C4 O3 -65.5(2) . . . . ? C9 O5 C4 C7 51.1(2) . . . . ? C9 O5 C4 C5 177.94(18) . . . . ? C3 O3 C4 O5 -88.70(18) . . . . ? C3 O3 C4 C7 148.42(17) . . . . ? C3 O3 C4 C5 26.2(2) . . . . ? C8 O4 C5 O2 -64.81(18) . . . . ? C8 O4 C5 C6 54.4(2) . . . . ? C8 O4 C5 C4 178.44(15) . . . . ? C2 O2 C5 O4 -51.27(17) . . . . ? C2 O2 C5 C6 -175.22(15) . . . . ? C2 O2 C5 C4 62.95(17) . . . . ? O5 C4 C5 O4 175.68(13) . . . . ? O3 C4 C5 O4 58.92(15) . . . . ? C7 C4 C5 O4 -57.26(18) . . . . ? O5 C4 C5 O2 57.55(17) . . . . ? O3 C4 C5 O2 -59.22(17) . . . . ? C7 C4 C5 O2 -175.40(15) . . . . ? O5 C4 C5 C6 -59.79(18) . . . . ? O3 C4 C5 C6 -176.56(15) . . . . ? C7 C4 C5 C6 67.3(2) . . . . ? C14 C1 C10 C11 54.46(19) . . . . ? C2 C1 C10 C11 -175.32(14) . . . . ? C1 C10 C11 O6 122.57(18) . . . . ? C1 C10 C11 C12 -55.00(19) . . . . ? O6 C11 C12 C13 -122.13(19) . . . . ? C10 C11 C12 C13 55.4(2) . . . . ? C11 C12 C13 C14 -55.9(2) . . . . ? C12 C13 C14 C1 55.97(18) . . . . ? C12 C13 C14 C18 -179.25(14) . . . . ? C10 C1 C14 C13 -55.06(18) . . . . ? C2 C1 C14 C13 177.39(13) . . . . ? C10 C1 C14 C18 -179.31(14) . . . . ? C2 C1 C14 C18 53.14(19) . . . . ? C13 C14 C18 C19 -71.67(19) . . . . ? C1 C14 C18 C19 51.2(2) . . . . ? C13 C14 C18 C20 53.8(2) . . . . ? C1 C14 C18 C20 176.60(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.331 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.103 data_sl0346 _database_code_depnum_ccdc_archive 'CCDC 283223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 O6' _chemical_formula_sum 'C14 H22 O6' _chemical_formula_weight 286.32 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5902(2) _cell_length_b 10.0809(2) _cell_length_c 16.5589(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1433.95(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6412 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9517 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3278 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+0.2875P] 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 0.1(8) _refine_ls_number_reflns 3278 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.54934(13) -0.01424(12) 0.42060(7) 0.0436(3) Uani 1 1 d . . . O2 O 0.87933(11) 0.01498(10) 0.28838(5) 0.0274(2) Uani 1 1 d . . . O3 O 0.58829(12) -0.10650(11) 0.30253(6) 0.0327(2) Uani 1 1 d . . . O4 O 0.68638(12) 0.09503(10) 0.20278(6) 0.0336(3) Uani 1 1 d . . . O5 O 0.78726(12) -0.23667(10) 0.25037(6) 0.0334(2) Uani 1 1 d . . . O6 O 1.21802(16) 0.17775(13) 0.52901(8) 0.0513(3) Uani 1 1 d . . . C1 C 0.88743(16) 0.02442(13) 0.43285(8) 0.0246(3) Uani 1 1 d . . . H1 H 0.8232 0.0475 0.4812 0.029 Uiso 1 1 calc R . . C2 C 0.78733(16) 0.04762(13) 0.35767(8) 0.0260(3) Uani 1 1 d . . . H2 H 0.7628 0.1445 0.3549 0.031 Uiso 1 1 calc R . . C3 C 0.63427(16) -0.02708(15) 0.36342(9) 0.0295(3) Uani 1 1 d . . . C4 C 0.68728(17) -0.13187(15) 0.23229(8) 0.0298(3) Uani 1 1 d . . . C5 C 0.79158(16) -0.01007(15) 0.21739(8) 0.0289(3) Uani 1 1 d . . . C6 C 0.90879(18) -0.03269(18) 0.15050(9) 0.0359(3) Uani 1 1 d . . . H6A H 0.9711 0.0478 0.1428 0.054 Uiso 1 1 calc R . . H6B H 0.8538 -0.0538 0.1003 0.054 Uiso 1 1 calc R . . H6C H 0.9773 -0.1066 0.1651 0.054 Uiso 1 1 calc R . . C7 C 0.57413(19) -0.16074(17) 0.16429(10) 0.0382(4) Uani 1 1 d . . . H7A H 0.5008 -0.2297 0.1814 0.057 Uiso 1 1 calc R . . H7B H 0.6318 -0.1915 0.1168 0.057 Uiso 1 1 calc R . . H7C H 0.5167 -0.0798 0.1507 0.057 Uiso 1 1 calc R . . C8 C 0.7574(2) 0.21924(18) 0.18255(12) 0.0449(4) Uani 1 1 d . . . H8A H 0.6797 0.2902 0.1861 0.067 Uiso 1 1 calc R . . H8B H 0.7985 0.2150 0.1274 0.067 Uiso 1 1 calc R . . H8C H 0.8427 0.2375 0.2203 0.067 Uiso 1 1 calc R . . C9 C 0.7150(2) -0.36446(16) 0.25876(11) 0.0410(4) Uani 1 1 d . . . H9A H 0.7920 -0.4288 0.2781 0.062 Uiso 1 1 calc R . . H9B H 0.6744 -0.3932 0.2063 0.062 Uiso 1 1 calc R . . H9C H 0.6293 -0.3585 0.2976 0.062 Uiso 1 1 calc R . . C10 C 1.02829(18) 0.11802(15) 0.43120(9) 0.0315(3) Uani 1 1 d . . . H10A H 1.0770 0.1131 0.3771 0.038 Uiso 1 1 calc R . . H10B H 0.9910 0.2101 0.4390 0.038 Uiso 1 1 calc R . . C11 C 1.15061(18) 0.08903(16) 0.49386(9) 0.0328(3) Uani 1 1 d . . . C12 C 1.18880(18) -0.05450(16) 0.50833(10) 0.0362(4) Uani 1 1 d . . . H12A H 1.2486 -0.0625 0.5592 0.043 Uiso 1 1 calc R . . H12B H 1.2555 -0.0872 0.4638 0.043 Uiso 1 1 calc R . . C13 C 1.04317(19) -0.14109(16) 0.51380(10) 0.0342(3) Uani 1 1 d . . . H13A H 0.9856 -0.1191 0.5638 0.041 Uiso 1 1 calc R . . H13B H 1.0743 -0.2355 0.5168 0.041 Uiso 1 1 calc R . . C14 C 0.93670(17) -0.12050(14) 0.44091(9) 0.0284(3) Uani 1 1 d . . . H14A H 0.9919 -0.1484 0.3912 0.034 Uiso 1 1 calc R . . H14B H 0.8429 -0.1768 0.4468 0.034 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 0.0299(5) 0.0559(7) 0.0450(7) -0.0076(6) 0.0146(5) -0.0052(6) O2 0.0222(5) 0.0372(5) 0.0228(4) 0.0011(4) 0.0009(4) -0.0002(4) O3 0.0258(5) 0.0385(6) 0.0339(5) 0.0001(4) 0.0021(4) -0.0066(5) O4 0.0247(5) 0.0358(6) 0.0403(6) 0.0133(5) -0.0023(5) -0.0009(5) O5 0.0291(5) 0.0335(5) 0.0377(6) 0.0046(5) -0.0037(5) 0.0003(5) O6 0.0445(7) 0.0520(7) 0.0573(8) -0.0179(6) -0.0068(6) -0.0133(6) C1 0.0246(6) 0.0245(6) 0.0246(6) -0.0005(5) 0.0039(5) -0.0012(6) C2 0.0231(6) 0.0270(6) 0.0279(7) 0.0013(5) 0.0031(6) 0.0016(6) C3 0.0238(7) 0.0307(7) 0.0339(7) 0.0031(6) 0.0011(6) 0.0019(6) C4 0.0253(7) 0.0372(8) 0.0269(7) 0.0039(6) -0.0010(6) -0.0017(6) C5 0.0247(6) 0.0363(8) 0.0259(7) 0.0052(6) -0.0040(5) -0.0021(6) C6 0.0292(7) 0.0520(9) 0.0264(7) 0.0009(7) 0.0008(6) -0.0036(7) C7 0.0349(8) 0.0423(9) 0.0373(8) 0.0029(7) -0.0113(7) -0.0046(7) C8 0.0383(10) 0.0384(8) 0.0580(11) 0.0179(8) 0.0000(8) -0.0032(7) C9 0.0399(9) 0.0367(8) 0.0464(9) 0.0083(7) 0.0016(8) 0.0000(7) C10 0.0333(7) 0.0281(7) 0.0331(8) 0.0002(6) 0.0002(7) -0.0055(6) C11 0.0275(7) 0.0412(8) 0.0297(7) -0.0060(6) 0.0049(6) -0.0065(7) C12 0.0305(8) 0.0438(9) 0.0344(8) -0.0012(7) -0.0055(7) 0.0010(7) C13 0.0372(8) 0.0334(8) 0.0319(7) 0.0046(6) -0.0025(7) 0.0014(7) C14 0.0289(7) 0.0247(6) 0.0316(7) 0.0003(6) -0.0014(6) -0.0006(6) _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 C3 1.2023(18) . ? O2 C5 1.4190(15) . ? O2 C2 1.4315(16) . ? O3 C3 1.3468(18) . ? O3 C4 1.4633(17) . ? O4 C5 1.4134(17) . ? O4 C8 1.4327(19) . ? O5 C4 1.3940(18) . ? O5 C9 1.4367(19) . ? O6 C11 1.2141(18) . ? C1 C14 1.5268(19) . ? C1 C2 1.5310(19) . ? C1 C10 1.5347(19) . ? C1 H1 1.0000 . ? C2 C3 1.5182(19) . ? C2 H2 1.0000 . ? C4 C7 1.516(2) . ? C4 C5 1.540(2) . ? C5 C6 1.514(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.505(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.503(2) . ? C12 C13 1.528(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.529(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 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 C5 O2 C2 114.30(10) . . ? C3 O3 C4 121.91(11) . . ? C5 O4 C8 115.02(11) . . ? C4 O5 C9 115.73(11) . . ? C14 C1 C2 111.90(11) . . ? C14 C1 C10 111.80(12) . . ? C2 C1 C10 109.54(11) . . ? C14 C1 H1 107.8 . . ? C2 C1 H1 107.8 . . ? C10 C1 H1 107.8 . . ? O2 C2 C3 114.49(11) . . ? O2 C2 C1 107.85(10) . . ? C3 C2 C1 111.08(11) . . ? O2 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? O1 C3 O3 118.40(13) . . ? O1 C3 C2 121.44(13) . . ? O3 C3 C2 120.12(12) . . ? O5 C4 O3 108.65(11) . . ? O5 C4 C7 114.15(13) . . ? O3 C4 C7 104.56(11) . . ? O5 C4 C5 106.27(11) . . ? O3 C4 C5 109.03(12) . . ? C7 C4 C5 114.03(12) . . ? O4 C5 O2 110.37(12) . . ? O4 C5 C6 114.38(11) . . ? O2 C5 C6 106.23(11) . . ? O4 C5 C4 104.66(11) . . ? O2 C5 C4 108.56(11) . . ? C6 C5 C4 112.58(13) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C1 114.75(12) . . ? C11 C10 H10A 108.6 . . ? C1 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O6 C11 C12 121.92(15) . . ? O6 C11 C10 121.36(15) . . ? C12 C11 C10 116.69(13) . . ? C11 C12 C13 112.38(13) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 111.44(12) . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C1 C14 C13 111.39(12) . . ? C1 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C1 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? 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 C5 O2 C2 C3 36.48(15) . . . . ? C5 O2 C2 C1 160.66(11) . . . . ? C14 C1 C2 O2 -61.81(14) . . . . ? C10 C1 C2 O2 62.75(14) . . . . ? C14 C1 C2 C3 64.40(15) . . . . ? C10 C1 C2 C3 -171.04(11) . . . . ? C4 O3 C3 O1 -177.45(13) . . . . ? C4 O3 C3 C2 4.72(19) . . . . ? O2 C2 C3 O1 176.20(13) . . . . ? C1 C2 C3 O1 53.76(18) . . . . ? O2 C2 C3 O3 -6.04(18) . . . . ? C1 C2 C3 O3 -128.48(13) . . . . ? C9 O5 C4 O3 68.70(15) . . . . ? C9 O5 C4 C7 -47.54(17) . . . . ? C9 O5 C4 C5 -174.10(12) . . . . ? C3 O3 C4 O5 85.73(15) . . . . ? C3 O3 C4 C7 -152.02(13) . . . . ? C3 O3 C4 C5 -29.70(17) . . . . ? C8 O4 C5 O2 66.76(16) . . . . ? C8 O4 C5 C6 -52.95(18) . . . . ? C8 O4 C5 C4 -176.62(13) . . . . ? C2 O2 C5 O4 51.55(14) . . . . ? C2 O2 C5 C6 176.07(11) . . . . ? C2 O2 C5 C4 -62.62(15) . . . . ? O5 C4 C5 O4 -177.54(10) . . . . ? O3 C4 C5 O4 -60.59(13) . . . . ? C7 C4 C5 O4 55.83(16) . . . . ? O5 C4 C5 O2 -59.68(14) . . . . ? O3 C4 C5 O2 57.27(14) . . . . ? C7 C4 C5 O2 173.69(12) . . . . ? O5 C4 C5 C6 57.64(15) . . . . ? O3 C4 C5 C6 174.59(11) . . . . ? C7 C4 C5 C6 -68.99(16) . . . . ? C14 C1 C10 C11 -45.12(17) . . . . ? C2 C1 C10 C11 -169.74(12) . . . . ? C1 C10 C11 O6 -140.99(15) . . . . ? C1 C10 C11 C12 41.17(19) . . . . ? O6 C11 C12 C13 137.81(15) . . . . ? C10 C11 C12 C13 -44.36(19) . . . . ? C11 C12 C13 C14 52.30(18) . . . . ? C2 C1 C14 C13 177.17(12) . . . . ? C10 C1 C14 C13 53.87(16) . . . . ? C12 C13 C14 C1 -58.09(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.160 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.032 data_sl0418 _database_code_depnum_ccdc_archive 'CCDC 283224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H27 Br O6,0.25(H2 O)' _chemical_formula_sum 'C17 H27.50 Br O6.25' _chemical_formula_weight 411.80 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' Br Br -0.2901 2.4595 '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 10.4635(3) _cell_length_b 9.3926(2) _cell_length_c 10.5987(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.8880(10) _cell_angle_gamma 90.00 _cell_volume 966.55(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6512 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 429 _exptl_absorpt_coefficient_mu 2.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.686 _exptl_absorpt_correction_T_max 0.775 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; One residual peak modelled as 1/4 water - this is a tentative assignment! (JED). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7897 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 27.42 _reflns_number_total 4050 _reflns_number_gt 3560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+3.8005P] 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 0.025(17) _refine_ls_number_reflns 4050 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1663 _refine_ls_wR_factor_gt 0.1591 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 Br1 Br 0.88686(8) 0.31794(8) 0.21049(8) 0.0498(2) Uani 1 1 d . . . O1 O 0.5335(5) -0.1277(5) -0.0483(4) 0.0331(10) Uani 1 1 d . . . C1 C 0.7245(6) 0.0585(6) 0.1650(6) 0.0245(11) Uani 1 1 d . . . H1 H 0.7236 0.0798 0.0722 0.029 Uiso 1 1 calc R . . O2 O 0.5790(5) 0.0015(5) 0.2850(4) 0.0264(9) Uani 1 1 d . . . C2 C 0.5768(6) 0.0137(7) 0.1509(6) 0.0260(12) Uani 1 1 d . . . H2 H 0.5128 0.0932 0.1049 0.031 Uiso 1 1 calc R . . O3 O 0.4721(5) -0.2267(4) 0.1080(4) 0.0317(10) Uani 1 1 d . . . C3 C 0.5285(6) -0.1188(7) 0.0645(6) 0.0276(12) Uani 1 1 d . . . O4 O 0.3404(6) -0.0166(6) 0.2027(6) 0.0395(12) Uani 1 1 d . . . C4 C 0.4705(6) -0.2284(7) 0.2457(6) 0.0309(13) Uani 1 1 d . . . O5 O 0.5942(5) -0.2823(5) 0.3349(5) 0.0339(10) Uani 1 1 d . . . C5 C 0.4643(6) -0.0742(7) 0.2925(7) 0.0304(13) Uani 1 1 d . . . O6 O 0.7706(5) 0.2555(6) 0.4712(5) 0.0443(12) Uani 1 1 d . . . C6 C 0.4813(8) -0.0650(8) 0.4421(7) 0.0404(16) Uani 1 1 d . . . H6A H 0.4963 0.0344 0.4722 0.061 Uiso 1 1 calc R . . H6B H 0.5606 -0.1225 0.4974 0.061 Uiso 1 1 calc R . . H6C H 0.3979 -0.1010 0.4526 0.061 Uiso 1 1 calc R . . C7 C 0.3454(9) -0.3168(9) 0.2326(9) 0.0426(18) Uani 1 1 d . . . H7A H 0.3555 -0.4124 0.2004 0.064 Uiso 1 1 calc R . . H7B H 0.2627 -0.2716 0.1676 0.064 Uiso 1 1 calc R . . H7C H 0.3371 -0.3238 0.3215 0.064 Uiso 1 1 calc R . . C8 C 0.3118(9) 0.1271(9) 0.2279(10) 0.053(2) Uani 1 1 d . . . H8A H 0.2341 0.1630 0.1497 0.079 Uiso 1 1 calc R . . H8B H 0.3932 0.1862 0.2419 0.079 Uiso 1 1 calc R . . H8C H 0.2887 0.1305 0.3093 0.079 Uiso 1 1 calc R . . C9 C 0.6339(9) -0.4216(8) 0.3058(8) 0.0438(18) Uani 1 1 d . . . H9A H 0.7206 -0.4497 0.3780 0.066 Uiso 1 1 calc R . . H9B H 0.6462 -0.4195 0.2185 0.066 Uiso 1 1 calc R . . H9C H 0.5619 -0.4905 0.3009 0.066 Uiso 1 1 calc R . . C10 C 0.7508(6) 0.1983(6) 0.2465(6) 0.0280(12) Uani 1 1 d . . . H10 H 0.6621 0.2522 0.2192 0.034 Uiso 1 1 calc R . . C11 C 0.8069(6) 0.1786(7) 0.4005(7) 0.0322(13) Uani 1 1 d . . . C12 C 0.9047(9) 0.0558(9) 0.4579(8) 0.052(2) Uani 1 1 d . . . H12A H 0.8579 -0.0178 0.4920 0.062 Uiso 1 1 calc R . . H12B H 0.9854 0.0901 0.5360 0.062 Uiso 1 1 calc R . . C13 C 0.9550(7) -0.0120(8) 0.3518(7) 0.0407(17) Uani 1 1 d . . . H13A H 1.0160 -0.0938 0.3929 0.049 Uiso 1 1 calc R . . H13B H 1.0082 0.0587 0.3222 0.049 Uiso 1 1 calc R . . C14 C 0.8291(6) -0.0628(7) 0.2279(6) 0.0271(12) Uani 1 1 d . . . H14 H 0.7805 -0.1352 0.2629 0.032 Uiso 1 1 calc R . . C18 C 0.8717(6) -0.1390(6) 0.1209(6) 0.0292(13) Uani 1 1 d . . . H18 H 0.7853 -0.1608 0.0415 0.035 Uiso 1 1 calc R . . C19 C 0.9626(9) -0.0465(10) 0.0676(9) 0.054(2) Uani 1 1 d . . . H19A H 0.9701 -0.0917 -0.0127 0.081 Uiso 1 1 calc R . . H19B H 1.0546 -0.0369 0.1386 0.081 Uiso 1 1 calc R . . H19C H 0.9209 0.0480 0.0430 0.081 Uiso 1 1 calc R . . C20 C 0.9427(8) -0.2805(8) 0.1736(9) 0.0455(18) Uani 1 1 d . . . H20A H 0.8785 -0.3444 0.1933 0.068 Uiso 1 1 calc R . . H20B H 1.0235 -0.2642 0.2568 0.068 Uiso 1 1 calc R . . H20C H 0.9718 -0.3238 0.1045 0.068 Uiso 1 1 calc R . . O1W O 0.1401(18) 0.315(3) 0.2089(19) 0.048(4) Uiso 0.25 1 d P . . 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 Br1 0.0536(4) 0.0312(3) 0.0739(5) -0.0071(4) 0.0346(4) -0.0179(3) O1 0.040(2) 0.036(3) 0.022(2) -0.0035(17) 0.0109(18) -0.0073(18) C1 0.030(3) 0.021(3) 0.024(3) 0.000(2) 0.011(2) -0.003(2) O2 0.033(2) 0.024(2) 0.025(2) -0.0036(16) 0.0139(17) -0.0054(18) C2 0.025(3) 0.030(3) 0.022(3) 0.001(2) 0.007(2) -0.002(2) O3 0.042(2) 0.027(2) 0.028(2) -0.0071(16) 0.0152(19) -0.0094(17) C3 0.026(3) 0.023(3) 0.032(3) -0.002(2) 0.008(2) -0.005(2) O4 0.031(2) 0.037(3) 0.054(3) -0.001(2) 0.020(2) 0.000(2) C4 0.034(3) 0.033(4) 0.030(3) 0.001(2) 0.015(3) -0.006(2) O5 0.035(2) 0.031(3) 0.035(2) 0.0010(19) 0.0109(19) 0.0051(19) C5 0.031(3) 0.031(4) 0.034(3) -0.001(3) 0.018(3) 0.000(2) O6 0.049(3) 0.041(3) 0.043(3) -0.020(2) 0.017(2) 0.002(2) C6 0.055(4) 0.040(4) 0.038(4) -0.006(3) 0.031(3) -0.009(3) C7 0.045(4) 0.036(4) 0.049(4) 0.000(3) 0.021(4) -0.015(3) C8 0.049(5) 0.039(4) 0.079(6) 0.012(4) 0.033(4) 0.010(3) C9 0.059(5) 0.025(4) 0.052(5) 0.004(3) 0.026(4) 0.006(3) C10 0.030(3) 0.020(3) 0.035(3) 0.001(2) 0.014(3) -0.002(2) C11 0.030(3) 0.030(3) 0.036(3) -0.010(3) 0.010(3) -0.002(2) C12 0.063(5) 0.049(5) 0.033(4) -0.008(3) 0.006(3) 0.026(4) C13 0.036(4) 0.040(4) 0.034(4) -0.009(3) -0.001(3) 0.016(3) C14 0.026(3) 0.025(3) 0.033(3) -0.001(2) 0.014(2) 0.007(2) C18 0.031(3) 0.028(4) 0.031(3) -0.002(2) 0.015(3) 0.005(2) C19 0.066(5) 0.056(5) 0.062(5) 0.014(4) 0.048(4) 0.009(4) C20 0.050(4) 0.031(4) 0.064(5) -0.007(3) 0.031(4) 0.008(3) _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 Br1 C10 1.960(6) . ? O1 C3 1.219(7) . ? C1 C10 1.539(8) . ? C1 C14 1.549(8) . ? C1 C2 1.554(8) . ? C1 H1 1.0000 . ? O2 C2 1.418(7) . ? O2 C5 1.422(7) . ? C2 C3 1.516(8) . ? C2 H2 1.0000 . ? O3 C3 1.338(7) . ? O3 C4 1.466(7) . ? O4 C5 1.400(8) . ? O4 C8 1.429(10) . ? C4 O5 1.383(8) . ? C4 C7 1.512(9) . ? C4 C5 1.540(9) . ? O5 C9 1.442(9) . ? C5 C6 1.531(9) . ? O6 C11 1.200(8) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.525(9) . ? C10 H10 1.0000 . ? C11 C12 1.511(10) . ? C12 C13 1.545(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.549(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C18 1.541(8) . ? C14 H14 1.0000 . ? C18 C20 1.523(10) . ? C18 C19 1.543(10) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C10 C1 C14 115.9(5) . . ? C10 C1 C2 104.4(5) . . ? C14 C1 C2 111.1(5) . . ? C10 C1 H1 108.4 . . ? C14 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? C2 O2 C5 113.5(4) . . ? O2 C2 C3 114.6(5) . . ? O2 C2 C1 106.4(4) . . ? C3 C2 C1 112.1(5) . . ? O2 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 O3 C4 121.4(5) . . ? O1 C3 O3 118.2(5) . . ? O1 C3 C2 121.4(5) . . ? O3 C3 C2 120.3(5) . . ? C5 O4 C8 116.3(6) . . ? O5 C4 O3 109.2(5) . . ? O5 C4 C7 114.7(6) . . ? O3 C4 C7 104.2(5) . . ? O5 C4 C5 105.3(5) . . ? O3 C4 C5 109.2(5) . . ? C7 C4 C5 114.1(6) . . ? C4 O5 C9 117.2(5) . . ? O4 C5 O2 110.9(5) . . ? O4 C5 C6 113.8(6) . . ? O2 C5 C6 104.8(5) . . ? O4 C5 C4 106.5(5) . . ? O2 C5 C4 108.3(5) . . ? C6 C5 C4 112.6(6) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C1 114.5(5) . . ? C11 C10 Br1 105.1(4) . . ? C1 C10 Br1 111.7(4) . . ? C11 C10 H10 108.5 . . ? C1 C10 H10 108.5 . . ? Br1 C10 H10 108.5 . . ? O6 C11 C12 122.2(6) . . ? O6 C11 C10 120.6(6) . . ? C12 C11 C10 117.2(5) . . ? C11 C12 C13 112.6(6) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 109.4(6) . . ? C12 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C18 C14 C1 112.2(5) . . ? C18 C14 C13 112.3(5) . . ? C1 C14 C13 112.3(5) . . ? C18 C14 H14 106.5 . . ? C1 C14 H14 106.5 . . ? C13 C14 H14 106.5 . . ? C20 C18 C14 111.8(5) . . ? C20 C18 C19 110.0(6) . . ? C14 C18 C19 113.3(6) . . ? C20 C18 H18 107.1 . . ? C14 C18 H18 107.1 . . ? C19 C18 H18 107.1 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C5 O2 C2 C3 -39.8(7) . . . . ? C5 O2 C2 C1 -164.3(5) . . . . ? C10 C1 C2 O2 -57.7(6) . . . . ? C14 C1 C2 O2 67.9(6) . . . . ? C10 C1 C2 C3 176.3(5) . . . . ? C14 C1 C2 C3 -58.1(6) . . . . ? C4 O3 C3 O1 175.9(5) . . . . ? C4 O3 C3 C2 -7.5(8) . . . . ? O2 C2 C3 O1 -173.2(5) . . . . ? C1 C2 C3 O1 -51.8(8) . . . . ? O2 C2 C3 O3 10.4(8) . . . . ? C1 C2 C3 O3 131.7(6) . . . . ? C3 O3 C4 O5 -84.4(7) . . . . ? C3 O3 C4 C7 152.5(6) . . . . ? C3 O3 C4 C5 30.3(7) . . . . ? O3 C4 O5 C9 -56.3(7) . . . . ? C7 C4 O5 C9 60.3(8) . . . . ? C5 C4 O5 C9 -173.5(5) . . . . ? C8 O4 C5 O2 -63.0(8) . . . . ? C8 O4 C5 C6 54.7(8) . . . . ? C8 O4 C5 C4 179.3(6) . . . . ? C2 O2 C5 O4 -52.7(7) . . . . ? C2 O2 C5 C6 -175.8(5) . . . . ? C2 O2 C5 C4 63.7(6) . . . . ? O5 C4 C5 O4 179.4(5) . . . . ? O3 C4 C5 O4 62.2(6) . . . . ? C7 C4 C5 O4 -53.9(7) . . . . ? O5 C4 C5 O2 60.1(6) . . . . ? O3 C4 C5 O2 -57.0(6) . . . . ? C7 C4 C5 O2 -173.2(6) . . . . ? O5 C4 C5 C6 -55.3(7) . . . . ? O3 C4 C5 C6 -172.5(5) . . . . ? C7 C4 C5 C6 71.4(8) . . . . ? C14 C1 C10 C11 -36.4(7) . . . . ? C2 C1 C10 C11 86.1(6) . . . . ? C14 C1 C10 Br1 82.9(5) . . . . ? C2 C1 C10 Br1 -154.7(4) . . . . ? C1 C10 C11 O6 -142.5(6) . . . . ? Br1 C10 C11 O6 94.6(7) . . . . ? C1 C10 C11 C12 35.3(8) . . . . ? Br1 C10 C11 C12 -87.7(7) . . . . ? O6 C11 C12 C13 -170.5(7) . . . . ? C10 C11 C12 C13 11.8(10) . . . . ? C11 C12 C13 C14 -57.5(9) . . . . ? C10 C1 C14 C18 -136.5(5) . . . . ? C2 C1 C14 C18 104.6(6) . . . . ? C10 C1 C14 C13 -9.0(7) . . . . ? C2 C1 C14 C13 -127.8(6) . . . . ? C12 C13 C14 C18 -177.0(6) . . . . ? C12 C13 C14 C1 55.6(8) . . . . ? C1 C14 C18 C20 -164.8(5) . . . . ? C13 C14 C18 C20 67.6(8) . . . . ? C1 C14 C18 C19 70.2(7) . . . . ? C13 C14 C18 C19 -57.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.769 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.108 data_sl0015 _database_code_depnum_ccdc_archive 'CCDC 283225' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H20 O7' _chemical_formula_weight 288.29 _chemical_melting_point ? _chemical_compound_source ? 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.9656(7) _cell_length_b 17.1331(13) _cell_length_c 8.0000(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.757(4) _cell_angle_gamma 90.00 _cell_volume 1341.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3175 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method ? _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 1.012 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5147 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.58 _reflns_number_total 2565 _reflns_number_observed 2307 _reflns_observed_criterion >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 teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.2711P] 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 ? _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 1.03(87) _refine_ls_number_reflns 2559 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_obs 0.0367 _refine_ls_wR_factor_all 0.1450 _refine_ls_wR_factor_obs 0.0835 _refine_ls_goodness_of_fit_all 1.073 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 1.785 _refine_ls_restrained_S_obs 1.087 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1957(2) 0.14514(9) 0.3927(2) 0.0422(4) Uani 1 d . . O2 O 0.27670(14) 0.21591(8) 0.21216(15) 0.0335(3) Uani 1 d . . O3 O 0.18589(13) 0.10509(7) -0.03221(14) 0.0278(3) Uani 1 d . . O4 O 0.41783(14) 0.10531(8) 0.0786(2) 0.0346(3) Uani 1 d . . O5 O 0.1890(2) 0.25991(8) -0.0506(2) 0.0373(3) Uani 1 d . . O6 O -0.2539(2) -0.00408(11) -0.2183(2) 0.0618(5) Uani 1 d . . O7 O -0.27580(14) 0.10570(9) -0.0951(2) 0.0387(4) Uani 1 d . . C1 C 0.2102(2) 0.15340(11) 0.2531(2) 0.0298(4) Uani 1 d . . C2 C 0.1515(2) 0.09365(11) 0.1248(2) 0.0267(4) Uani 1 d . . H2 H 0.1869(2) 0.04137(11) 0.1679(2) 0.032 Uiso 1 calc R . C3 C 0.3123(2) 0.14397(12) -0.0284(2) 0.0298(4) Uani 1 d . . C4 C 0.3024(2) 0.22533(12) 0.0458(2) 0.0320(4) Uani 1 d . . C5 C 0.3336(2) 0.14686(13) -0.2031(2) 0.0394(5) Uani 1 d . . H5A H 0.2652(11) 0.1812(8) -0.2699(5) 0.059 Uiso 1 calc R . H5B H 0.3247(16) 0.0942(2) -0.2519(7) 0.059 Uiso 1 calc R . H5C H 0.4252(7) 0.1671(9) -0.2054(3) 0.059 Uiso 1 calc R . C6 C 0.4320(3) 0.27291(14) 0.0667(3) 0.0452(5) Uani 1 d . . H6A H 0.5077(4) 0.2430(4) 0.1325(18) 0.068 Uiso 1 calc R . H6B H 0.4201(6) 0.3215(5) 0.1268(19) 0.068 Uiso 1 calc R . H6C H 0.4524(10) 0.2851(8) -0.0456(3) 0.068 Uiso 1 calc R . C7 C 0.4466(2) 0.02765(13) 0.0305(3) 0.0395(5) Uani 1 d . . H7A H 0.5099(13) 0.0028(3) 0.1237(8) 0.059 Uiso 1 calc R . H7B H 0.4881(15) 0.02933(14) -0.0712(12) 0.059 Uiso 1 calc R . H7C H 0.3615(3) -0.0024(3) 0.0061(19) 0.059 Uiso 1 calc R . C8 C 0.1533(3) 0.33724(13) -0.0083(3) 0.0510(6) Uani 1 d . . H8A H 0.0637(8) 0.3509(4) -0.0754(16) 0.076 Uiso 1 calc R . H8B H 0.2220(10) 0.3741(2) -0.0337(21) 0.076 Uiso 1 calc R . H8C H 0.1496(18) 0.3398(3) 0.1131(5) 0.076 Uiso 1 calc R . C9 C -0.0045(2) 0.09262(11) 0.1052(2) 0.0288(4) Uani 1 d . . H9 H -0.0267(2) 0.07825(11) 0.2181(2) 0.035 Uiso 1 calc R . C10 C -0.0632(2) 0.03034(13) -0.0198(3) 0.0431(5) Uani 1 d . . H10A H -0.0019(2) 0.02435(13) -0.1031(3) 0.052 Uiso 1 calc R . H10B H -0.0615(2) -0.01959(13) 0.0428(3) 0.052 Uiso 1 calc R . C11 C -0.2035(2) 0.04240(13) -0.1155(3) 0.0374(5) Uani 1 d . . C12 C -0.0717(2) 0.17082(11) 0.0535(2) 0.0316(4) Uani 1 d . . H12A H -0.0390(2) 0.21046(11) 0.1418(2) 0.038 Uiso 1 calc R . H12B H -0.0477(2) 0.18845(11) -0.0550(2) 0.038 Uiso 1 calc R . C13 C -0.2244(2) 0.16168(13) 0.0330(3) 0.0352(5) Uani 1 d . . H13A H -0.2475(2) 0.14499(13) 0.1427(3) 0.042 Uiso 1 calc R . H13B H -0.2688(2) 0.21270(13) 0.0022(3) 0.042 Uiso 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 0.0558(10) 0.0521(10) 0.0190(7) -0.0002(6) 0.0075(6) -0.0104(8) O2 0.0433(8) 0.0358(8) 0.0219(6) -0.0054(5) 0.0077(5) -0.0101(7) O3 0.0311(7) 0.0323(7) 0.0195(6) -0.0025(5) 0.0034(5) -0.0017(6) O4 0.0323(7) 0.0411(9) 0.0292(7) 0.0027(5) 0.0027(5) 0.0011(6) O5 0.0496(9) 0.0311(8) 0.0299(7) -0.0015(6) 0.0041(6) 0.0022(7) O6 0.0584(11) 0.0583(11) 0.0591(11) -0.0195(9) -0.0139(8) -0.0058(9) O7 0.0293(7) 0.0434(9) 0.0416(8) 0.0039(6) 0.0015(6) 0.0014(7) C1 0.0306(9) 0.0345(10) 0.0229(9) 0.0003(7) 0.0017(7) -0.0004(9) C2 0.0306(10) 0.0294(10) 0.0203(8) 0.0013(7) 0.0049(7) 0.0015(8) C3 0.0321(10) 0.0340(11) 0.0232(8) 0.0012(7) 0.0051(7) -0.0019(8) C4 0.0379(11) 0.0364(10) 0.0224(9) 0.0016(7) 0.0071(8) -0.0049(9) C5 0.0497(12) 0.0436(13) 0.0278(10) -0.0011(8) 0.0150(9) 0.0013(10) C6 0.0488(13) 0.0468(13) 0.0414(11) -0.0018(10) 0.0119(9) -0.0139(11) C7 0.0367(11) 0.0408(12) 0.0420(11) 0.0039(9) 0.0098(9) 0.0056(10) C8 0.075(2) 0.0319(12) 0.0456(13) -0.0030(10) 0.0097(12) 0.0065(12) C9 0.0293(10) 0.0284(10) 0.0279(9) 0.0017(7) 0.0029(7) -0.0023(8) C10 0.0371(11) 0.0326(12) 0.0554(13) -0.0127(9) -0.0021(10) -0.0010(10) C11 0.0343(11) 0.0386(12) 0.0387(10) 0.0003(9) 0.0050(8) -0.0070(10) C12 0.0346(10) 0.0283(10) 0.0311(9) -0.0003(8) 0.0043(7) 0.0032(9) C13 0.0343(11) 0.0394(11) 0.0332(9) 0.0035(8) 0.0096(8) 0.0061(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 O1 C1 1.161(2) . ? O2 C1 1.332(2) . ? O2 C4 1.410(2) . ? O3 C2 1.376(2) . ? O3 C3 1.421(2) . ? O4 C3 1.393(2) . ? O4 C7 1.429(3) . ? O5 C4 1.378(2) . ? O5 C8 1.429(3) . ? O6 C11 1.187(3) . ? O7 C11 1.329(3) . ? O7 C13 1.427(3) . ? C1 C2 1.490(2) . ? C2 C9 1.533(3) . ? C2 H2 1.00 . ? C3 C5 1.453(2) . ? C3 C4 1.526(3) . ? C4 C6 1.510(3) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 C10 1.504(3) . ? C9 C12 1.520(3) . ? C9 H9 1.00 . ? C10 C11 1.478(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C12 C13 1.507(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 120.67(14) . . ? C2 O3 C3 114.73(13) . . ? C3 O4 C7 116.3(2) . . ? C4 O5 C8 118.7(2) . . ? C11 O7 C13 120.4(2) . . ? O1 C1 O2 119.4(2) . . ? O1 C1 C2 118.4(2) . . ? O2 C1 C2 122.18(15) . . ? O3 C2 C1 113.5(2) . . ? O3 C2 C9 109.19(13) . . ? C1 C2 C9 109.79(15) . . ? O3 C2 H2 108.08(10) . . ? C1 C2 H2 108.08(10) . . ? C9 C2 H2 108.08(10) . . ? O4 C3 O3 110.78(15) . . ? O4 C3 C5 112.2(2) . . ? O3 C3 C5 106.5(2) . . ? O4 C3 C4 106.94(14) . . ? O3 C3 C4 108.4(2) . . ? C5 C3 C4 112.0(2) . . ? O5 C4 O2 107.6(2) . . ? O5 C4 C6 115.2(2) . . ? O2 C4 C6 105.1(2) . . ? O5 C4 C3 106.30(15) . . ? O2 C4 C3 107.41(14) . . ? C6 C4 C3 114.8(2) . . ? C3 C5 H5A 109.47(12) . . ? C3 C5 H5B 109.47(12) . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.47(12) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.47(13) . . ? C4 C6 H6B 109.47(12) . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.47(11) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 H7A 109.47(10) . . ? O4 C7 H7B 109.47(10) . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.47(11) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 H8A 109.47(12) . . ? O5 C8 H8B 109.47(13) . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.47(11) . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C12 110.3(2) . . ? C10 C9 C2 109.7(2) . . ? C12 C9 C2 113.9(2) . . ? C10 C9 H9 107.56(12) . . ? C12 C9 H9 107.56(10) . . ? C2 C9 H9 107.56(9) . . ? C11 C10 C9 117.3(2) . . ? C11 C10 H10A 107.98(12) . . ? C9 C10 H10A 107.98(12) . . ? C11 C10 H10B 107.98(13) . . ? C9 C10 H10B 107.98(12) . . ? H10A C10 H10B 107.2 . . ? O6 C11 O7 117.6(2) . . ? O6 C11 C10 120.2(2) . . ? O7 C11 C10 122.2(2) . . ? C13 C12 C9 108.8(2) . . ? C13 C12 H12A 109.92(10) . . ? C9 C12 H12A 109.92(10) . . ? C13 C12 H12B 109.92(10) . . ? C9 C12 H12B 109.92(10) . . ? H12A C12 H12B 108.3 . . ? O7 C13 C12 111.6(2) . . ? O7 C13 H13A 109.31(10) . . ? C12 C13 H13A 109.31(10) . . ? O7 C13 H13B 109.31(10) . . ? C12 C13 H13B 109.31(11) . . ? H13A C13 H13B 108.0 . . ? 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 C4 O2 C1 O1 176.5(2) . . . . ? C4 O2 C1 C2 -4.3(3) . . . . ? C3 O3 C2 C1 27.9(2) . . . . ? C3 O3 C2 C9 150.8(2) . . . . ? O1 C1 C2 O3 -174.0(2) . . . . ? O2 C1 C2 O3 6.8(3) . . . . ? O1 C1 C2 C9 63.5(2) . . . . ? O2 C1 C2 C9 -115.7(2) . . . . ? C7 O4 C3 O3 63.2(2) . . . . ? C7 O4 C3 C5 -55.7(2) . . . . ? C7 O4 C3 C4 -178.9(2) . . . . ? C2 O3 C3 O4 54.8(2) . . . . ? C2 O3 C3 C5 177.1(2) . . . . ? C2 O3 C3 C4 -62.2(2) . . . . ? C8 O5 C4 O2 64.5(2) . . . . ? C8 O5 C4 C6 -52.3(2) . . . . ? C8 O5 C4 C3 179.3(2) . . . . ? C1 O2 C4 O5 85.4(2) . . . . ? C1 O2 C4 C6 -151.4(2) . . . . ? C1 O2 C4 C3 -28.7(2) . . . . ? O4 C3 C4 O5 -173.85(14) . . . . ? O3 C3 C4 O5 -54.4(2) . . . . ? C5 C3 C4 O5 62.8(2) . . . . ? O4 C3 C4 O2 -58.9(2) . . . . ? O3 C3 C4 O2 60.6(2) . . . . ? C5 C3 C4 O2 177.8(2) . . . . ? O4 C3 C4 C6 57.6(2) . . . . ? O3 C3 C4 C6 177.0(2) . . . . ? C5 C3 C4 C6 -65.8(2) . . . . ? O3 C2 C9 C10 57.0(2) . . . . ? C1 C2 C9 C10 -178.0(2) . . . . ? O3 C2 C9 C12 -67.2(2) . . . . ? C1 C2 C9 C12 57.8(2) . . . . ? C12 C9 C10 C11 -25.9(3) . . . . ? C2 C9 C10 C11 -152.2(2) . . . . ? C13 O7 C11 O6 176.4(2) . . . . ? C13 O7 C11 C10 -5.8(3) . . . . ? C9 C10 C11 O6 178.5(2) . . . . ? C9 C10 C11 O7 0.7(3) . . . . ? C10 C9 C12 C13 54.3(2) . . . . ? C2 C9 C12 C13 178.22(14) . . . . ? C11 O7 C13 C12 36.2(2) . . . . ? C9 C12 C13 O7 -60.4(2) . . . . ? _refine_diff_density_max 0.149 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040