# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0092_080113_kms_d_167_0m #TrackingRef 'web_deposit_cif_file_0_KanaM.Sureshan_1361278898.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 O6' _chemical_formula_sum 'C12 H20 O6' _chemical_formula_weight 260.28 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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.6971(2) _cell_length_b 11.5145(3) _cell_length_c 19.4201(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1273.94(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5260 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 28.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.355 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9786 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5497 _diffrn_reflns_av_R_equivalents 0.0119 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2187 _reflns_number_gt 2133 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0487P)^2^+0.2423P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(9) _refine_ls_number_reflns 2187 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5745(3) 0.21604(12) 0.72636(7) 0.0280(3) Uani 1 1 d . . . H1 H 0.6951 0.2628 0.7493 0.034 Uiso 1 1 calc R . . C2 C 0.4282(3) 0.29436(12) 0.67888(7) 0.0306(3) Uani 1 1 d . . . H2 H 0.5179 0.3644 0.6675 0.037 Uiso 1 1 calc R . . C3 C 0.1914(3) 0.32855(13) 0.70868(8) 0.0319(3) Uani 1 1 d . . . H3 H 0.0841 0.2628 0.7027 0.038 Uiso 1 1 calc R . . C4 C 0.2236(3) 0.34896(13) 0.78627(8) 0.0336(3) Uani 1 1 d . . . H4 H 0.3624 0.3976 0.7938 0.040 Uiso 1 1 calc R . . C5 C 0.2605(3) 0.23207(13) 0.82045(8) 0.0312(3) Uani 1 1 d . . . H5 H 0.1090 0.1930 0.8265 0.037 Uiso 1 1 calc R . . C6 C 0.4305(3) 0.15219(12) 0.78026(7) 0.0289(3) Uani 1 1 d . . . H6 H 0.3431 0.0885 0.7587 0.035 Uiso 1 1 calc R . . C7 C 0.6025(3) 0.15589(14) 0.61099(7) 0.0345(3) Uani 1 1 d . . . C8 C 0.7922(3) 0.21729(17) 0.57099(9) 0.0473(4) Uani 1 1 d . . . H8A H 0.9263 0.1674 0.5668 0.071 Uiso 1 1 calc R . . H8B H 0.8363 0.2871 0.5947 0.071 Uiso 1 1 calc R . . H8C H 0.7346 0.2365 0.5259 0.071 Uiso 1 1 calc R . . C9 C 0.5296(4) 0.04243(18) 0.57898(10) 0.0588(5) Uani 1 1 d . . . H9A H 0.6650 -0.0062 0.5731 0.088 Uiso 1 1 calc R . . H9B H 0.4586 0.0569 0.5350 0.088 Uiso 1 1 calc R . . H9C H 0.4186 0.0042 0.6085 0.088 Uiso 1 1 calc R . . C10 C 0.5100(3) 0.14733(13) 0.89916(7) 0.0330(3) Uani 1 1 d . . . C11 C 0.7222(3) 0.18434(18) 0.93906(9) 0.0498(5) Uani 1 1 d . . . H11A H 0.8182 0.1178 0.9487 0.075 Uiso 1 1 calc R . . H11B H 0.6739 0.2196 0.9815 0.075 Uiso 1 1 calc R . . H11C H 0.8106 0.2394 0.9125 0.075 Uiso 1 1 calc R . . C12 C 0.3714(4) 0.05238(15) 0.93393(9) 0.0468(4) Uani 1 1 d . . . H12A H 0.4719 -0.0130 0.9424 0.070 Uiso 1 1 calc R . . H12B H 0.2440 0.0291 0.9047 0.070 Uiso 1 1 calc R . . H12C H 0.3102 0.0806 0.9768 0.070 Uiso 1 1 calc R . . O1 O 0.6845(2) 0.13521(9) 0.68072(5) 0.0360(3) Uani 1 1 d . . . O2 O 0.3986(2) 0.22525(10) 0.61863(5) 0.0390(3) Uani 1 1 d . . . O3 O 0.0912(2) 0.42649(9) 0.67502(7) 0.0445(3) Uani 1 1 d . . . H3A H 0.1404 0.4862 0.6929 0.067 Uiso 1 1 calc R . . O4 O 0.0255(2) 0.40274(11) 0.81691(7) 0.0505(3) Uani 1 1 d . . . H4A H 0.0032 0.4662 0.7989 0.076 Uiso 1 1 calc R . . O5 O 0.3710(2) 0.24643(9) 0.88545(5) 0.0390(3) Uani 1 1 d . . . O6 O 0.5846(2) 0.10748(9) 0.83187(5) 0.0393(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0265(7) 0.0285(7) 0.0289(7) -0.0015(5) -0.0023(6) -0.0005(6) C2 0.0311(7) 0.0308(7) 0.0300(7) 0.0042(6) -0.0031(6) -0.0041(6) C3 0.0279(7) 0.0267(7) 0.0411(8) 0.0062(6) -0.0047(6) -0.0021(6) C4 0.0302(7) 0.0288(7) 0.0419(8) -0.0023(6) -0.0001(6) 0.0017(6) C5 0.0304(7) 0.0310(7) 0.0323(7) -0.0011(6) 0.0022(6) -0.0004(6) C6 0.0339(7) 0.0255(6) 0.0272(7) -0.0012(6) -0.0023(6) -0.0009(6) C7 0.0376(8) 0.0394(8) 0.0265(7) 0.0010(6) -0.0040(7) 0.0028(7) C8 0.0442(9) 0.0629(11) 0.0347(8) 0.0075(8) 0.0030(7) 0.0014(9) C9 0.0767(14) 0.0495(10) 0.0502(10) -0.0109(9) -0.0123(10) -0.0035(11) C10 0.0417(8) 0.0322(7) 0.0252(7) -0.0024(6) 0.0042(6) 0.0041(7) C11 0.0486(10) 0.0605(11) 0.0402(9) -0.0032(8) -0.0029(8) -0.0028(9) C12 0.0594(11) 0.0418(9) 0.0393(9) 0.0035(8) 0.0103(8) -0.0025(9) O1 0.0413(6) 0.0420(6) 0.0245(5) 0.0010(5) 0.0019(5) 0.0112(5) O2 0.0370(6) 0.0500(6) 0.0299(5) -0.0018(5) -0.0064(5) 0.0052(6) O3 0.0372(6) 0.0354(6) 0.0609(7) 0.0105(5) -0.0121(6) 0.0033(5) O4 0.0488(7) 0.0448(7) 0.0578(8) -0.0037(6) 0.0075(6) 0.0167(6) O5 0.0517(7) 0.0353(6) 0.0299(5) -0.0053(5) 0.0007(5) 0.0097(5) O6 0.0531(7) 0.0416(6) 0.0232(5) 0.0012(4) 0.0037(5) 0.0197(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4300(17) . ? C1 C6 1.5197(19) . ? C1 C2 1.536(2) . ? C1 H1 0.9800 . ? C2 O2 1.4250(18) . ? C2 C3 1.520(2) . ? C2 H2 0.9800 . ? C3 O3 1.4227(18) . ? C3 C4 1.536(2) . ? C3 H3 0.9800 . ? C4 O4 1.4180(19) . ? C4 C5 1.515(2) . ? C4 H4 0.9800 . ? C5 O5 1.4202(19) . ? C5 C6 1.547(2) . ? C5 H5 0.9800 . ? C6 O6 1.4286(18) . ? C6 H6 0.9800 . ? C7 O2 1.418(2) . ? C7 O1 1.4522(18) . ? C7 C9 1.505(2) . ? C7 C8 1.507(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O5 1.4141(19) . ? C10 O6 1.4489(16) . ? C10 C11 1.498(2) . ? C10 C12 1.508(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O3 H3A 0.8200 . ? O4 H4A 0.8200 . ? 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 O1 C1 C6 110.41(11) . . ? O1 C1 C2 104.36(11) . . ? C6 C1 C2 113.87(12) . . ? O1 C1 H1 109.3 . . ? C6 C1 H1 109.3 . . ? C2 C1 H1 109.3 . . ? O2 C2 C3 110.62(12) . . ? O2 C2 C1 103.25(11) . . ? C3 C2 C1 113.91(12) . . ? O2 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? O3 C3 C2 112.72(13) . . ? O3 C3 C4 112.16(13) . . ? C2 C3 C4 107.87(12) . . ? O3 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? O4 C4 C5 108.32(13) . . ? O4 C4 C3 112.54(13) . . ? C5 C4 C3 108.09(12) . . ? O4 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? O5 C5 C4 110.33(12) . . ? O5 C5 C6 103.89(12) . . ? C4 C5 C6 113.19(12) . . ? O5 C5 H5 109.8 . . ? C4 C5 H5 109.8 . . ? C6 C5 H5 109.8 . . ? O6 C6 C1 109.00(12) . . ? O6 C6 C5 104.19(10) . . ? C1 C6 C5 113.45(11) . . ? O6 C6 H6 110.0 . . ? C1 C6 H6 110.0 . . ? C5 C6 H6 110.0 . . ? O2 C7 O1 104.97(11) . . ? O2 C7 C9 107.80(15) . . ? O1 C7 C9 109.37(14) . . ? O2 C7 C8 112.17(13) . . ? O1 C7 C8 109.10(13) . . ? C9 C7 C8 113.10(15) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 O6 104.48(11) . . ? O5 C10 C11 108.65(13) . . ? O6 C10 C11 108.64(13) . . ? O5 C10 C12 112.10(14) . . ? O6 C10 C12 109.15(12) . . ? C11 C10 C12 113.40(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 O1 C7 109.28(11) . . ? C7 O2 C2 107.67(11) . . ? C3 O3 H3A 109.5 . . ? C4 O4 H4A 109.5 . . ? C10 O5 C5 108.77(11) . . ? C6 O6 C10 109.77(11) . . ? 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 O1 C1 C2 O2 21.50(14) . . . . ? C6 C1 C2 O2 -98.97(13) . . . . ? O1 C1 C2 C3 141.52(12) . . . . ? C6 C1 C2 C3 21.05(17) . . . . ? O2 C2 C3 O3 -82.15(15) . . . . ? C1 C2 C3 O3 162.09(12) . . . . ? O2 C2 C3 C4 153.46(11) . . . . ? C1 C2 C3 C4 37.70(16) . . . . ? O3 C3 C4 O4 43.83(18) . . . . ? C2 C3 C4 O4 168.56(12) . . . . ? O3 C3 C4 C5 163.41(13) . . . . ? C2 C3 C4 C5 -71.87(15) . . . . ? O4 C4 C5 O5 -78.33(16) . . . . ? C3 C4 C5 O5 159.47(12) . . . . ? O4 C4 C5 C6 165.75(12) . . . . ? C3 C4 C5 C6 43.55(17) . . . . ? O1 C1 C6 O6 78.09(13) . . . . ? C2 C1 C6 O6 -164.90(12) . . . . ? O1 C1 C6 C5 -166.32(12) . . . . ? C2 C1 C6 C5 -49.31(16) . . . . ? O5 C5 C6 O6 14.05(15) . . . . ? C4 C5 C6 O6 133.73(13) . . . . ? O5 C5 C6 C1 -104.36(13) . . . . ? C4 C5 C6 C1 15.32(17) . . . . ? C6 C1 O1 C7 119.29(13) . . . . ? C2 C1 O1 C7 -3.46(15) . . . . ? O2 C7 O1 C1 -16.07(15) . . . . ? C9 C7 O1 C1 -131.51(15) . . . . ? C8 C7 O1 C1 104.32(15) . . . . ? O1 C7 O2 C2 30.81(15) . . . . ? C9 C7 O2 C2 147.32(13) . . . . ? C8 C7 O2 C2 -87.53(15) . . . . ? C3 C2 O2 C7 -154.72(12) . . . . ? C1 C2 O2 C7 -32.48(15) . . . . ? O6 C10 O5 C5 30.65(16) . . . . ? C11 C10 O5 C5 146.47(13) . . . . ? C12 C10 O5 C5 -87.41(15) . . . . ? C4 C5 O5 C10 -149.50(13) . . . . ? C6 C5 O5 C10 -27.89(15) . . . . ? C1 C6 O6 C10 125.48(13) . . . . ? C5 C6 O6 C10 4.07(15) . . . . ? O5 C10 O6 C6 -20.83(16) . . . . ? C11 C10 O6 C6 -136.66(14) . . . . ? C12 C10 O6 C6 99.23(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O6 0.82 2.15 2.7878(16) 134.3 3_656 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.195 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 925397' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_output #TrackingRef 'web_deposit_cif_file_1_KanaM.Sureshan_1361278898.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 O10' _chemical_formula_sum 'C20 H28 O10' _chemical_formula_weight 428.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 12.681(4) _cell_length_b 18.138(5) _cell_length_c 9.663(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.551(7) _cell_angle_gamma 90.00 _cell_volume 2208.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2729 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.284 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8591 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3430 _reflns_number_gt 2744 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0687P)^2^+0.0658P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(11) _refine_ls_number_reflns 3430 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7748(2) 0.05317(15) 0.6608(3) 0.0442(7) Uani 1 1 d . . . H1 H 0.7688 0.0423 0.7589 0.053 Uiso 1 1 calc R . . C2 C 0.7495(2) 0.13398(15) 0.6322(3) 0.0471(7) Uani 1 1 d . . . H2 H 0.7759 0.1635 0.7138 0.057 Uiso 1 1 calc R . . C3 C 0.6334(3) 0.15037(15) 0.5916(3) 0.0519(8) Uani 1 1 d . . . H3 H 0.5957 0.1449 0.6741 0.062 Uiso 1 1 calc R . . C4 C 0.5848(2) 0.09830(16) 0.4802(3) 0.0471(7) Uani 1 1 d . . . H4 H 0.6234 0.1009 0.3980 0.057 Uiso 1 1 calc R . . C5 C 0.5917(2) 0.02025(16) 0.5419(3) 0.0467(7) Uani 1 1 d . . . H5 H 0.5595 0.0193 0.6293 0.056 Uiso 1 1 calc R . . C6 C 0.7071(2) -0.00165(15) 0.5685(3) 0.0408(6) Uani 1 1 d . . . H6 H 0.7361 -0.0064 0.4792 0.049 Uiso 1 1 calc R . . C7 C 0.9089(2) 0.11165(14) 0.5558(3) 0.0447(6) Uani 1 1 d . . . C8 C 0.9507(3) 0.08793(17) 0.4237(3) 0.0589(8) Uani 1 1 d . . . H8A H 0.9568 0.1307 0.3647 0.071 Uiso 1 1 calc R . . H8B H 0.9009 0.0539 0.3740 0.071 Uiso 1 1 calc R . . C9 C 1.0594(3) 0.0506(2) 0.4524(4) 0.0758(10) Uani 1 1 d . . . H9A H 1.0518 0.0044 0.5008 0.091 Uiso 1 1 calc R . . H9B H 1.0865 0.0397 0.3648 0.091 Uiso 1 1 calc R . . C10 C 1.1377(3) 0.0999(2) 0.5403(4) 0.0776(10) Uani 1 1 d . . . H10A H 1.2046 0.0741 0.5616 0.093 Uiso 1 1 calc R . . H10B H 1.1508 0.1440 0.4882 0.093 Uiso 1 1 calc R . . C11 C 1.0946(3) 0.1209(2) 0.6732(4) 0.0676(9) Uani 1 1 d . . . H11A H 1.1441 0.1540 0.7262 0.081 Uiso 1 1 calc R . . H11B H 1.0874 0.0771 0.7289 0.081 Uiso 1 1 calc R . . C12 C 0.9878(3) 0.15836(18) 0.6439(3) 0.0569(8) Uani 1 1 d . . . H12A H 0.9606 0.1692 0.7315 0.068 Uiso 1 1 calc R . . H12B H 0.9967 0.2048 0.5967 0.068 Uiso 1 1 calc R . . C13 C 0.5781(3) 0.27395(18) 0.6233(3) 0.0603(8) Uani 1 1 d . . . C14 C 0.5681(4) 0.3485(2) 0.5621(4) 0.0764(10) Uani 1 1 d . . . H14A H 0.5921 0.3479 0.4714 0.115 Uiso 1 1 calc R . . H14B H 0.6106 0.3824 0.6209 0.115 Uiso 1 1 calc R . . H14C H 0.4952 0.3638 0.5542 0.115 Uiso 1 1 calc R . . C15 C 0.4487(3) 0.14708(18) 0.3163(4) 0.0594(8) Uani 1 1 d . . . C16 C 0.3341(3) 0.1639(3) 0.2934(5) 0.0929(13) Uani 1 1 d . . . H16A H 0.3013 0.1499 0.3742 0.139 Uiso 1 1 calc R . . H16B H 0.3022 0.1369 0.2139 0.139 Uiso 1 1 calc R . . H16C H 0.3244 0.2158 0.2771 0.139 Uiso 1 1 calc R . . C17 C 0.4396(3) -0.0531(2) 0.4665(4) 0.0663(9) Uani 1 1 d . . . C18 C 0.4000(4) -0.1090(3) 0.3618(5) 0.1055(15) Uani 1 1 d . . . H18A H 0.4526 -0.1176 0.2997 0.158 Uiso 1 1 calc R . . H18B H 0.3358 -0.0915 0.3098 0.158 Uiso 1 1 calc R . . H18C H 0.3857 -0.1542 0.4081 0.158 Uiso 1 1 calc R . . C19 C 0.7536(3) -0.13043(17) 0.5760(3) 0.0505(7) Uani 1 1 d . . . C20 C 0.7516(3) -0.19798(17) 0.6619(3) 0.0635(9) Uani 1 1 d . . . H20A H 0.7209 -0.1868 0.7458 0.095 Uiso 1 1 calc R . . H20B H 0.8227 -0.2158 0.6853 0.095 Uiso 1 1 calc R . . H20C H 0.7099 -0.2351 0.6103 0.095 Uiso 1 1 calc R . . O1 O 0.88282(16) 0.04751(11) 0.6361(2) 0.0528(5) Uani 1 1 d . . . O2 O 0.81079(16) 0.14905(10) 0.52143(18) 0.0481(5) Uani 1 1 d . . . O3 O 0.62120(19) 0.22549(11) 0.5423(2) 0.0602(6) Uani 1 1 d . . . O4 O 0.5550(4) 0.25746(16) 0.7350(3) 0.1260(15) Uani 1 1 d . . . O5 O 0.47596(16) 0.11690(12) 0.4438(2) 0.0581(6) Uani 1 1 d . . . O6 O 0.5111(2) 0.15912(15) 0.2352(2) 0.0774(7) Uani 1 1 d . . . O7 O 0.53949(16) -0.03141(11) 0.4461(2) 0.0541(5) Uani 1 1 d . . . O8 O 0.3943(2) -0.02939(17) 0.5593(3) 0.0848(8) Uani 1 1 d . . . O9 O 0.71422(15) -0.07201(10) 0.63871(18) 0.0455(5) Uani 1 1 d . . . O10 O 0.7871(3) -0.12657(15) 0.4668(3) 0.0951(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0596(19) 0.0409(15) 0.0332(13) 0.0037(11) 0.0097(12) -0.0061(13) C2 0.067(2) 0.0411(15) 0.0339(14) 0.0014(11) 0.0067(14) -0.0043(13) C3 0.070(2) 0.0418(16) 0.0470(15) 0.0070(13) 0.0214(14) 0.0059(15) C4 0.0455(18) 0.0498(16) 0.0479(15) 0.0061(13) 0.0138(12) 0.0048(14) C5 0.0517(18) 0.0449(16) 0.0451(14) 0.0011(13) 0.0126(12) -0.0013(13) C6 0.0492(17) 0.0375(14) 0.0373(13) 0.0050(11) 0.0117(12) -0.0015(12) C7 0.0545(18) 0.0339(14) 0.0449(14) 0.0071(12) 0.0020(12) -0.0041(13) C8 0.070(2) 0.0547(19) 0.0532(17) -0.0026(14) 0.0108(15) -0.0071(16) C9 0.085(3) 0.060(2) 0.086(2) 0.0002(19) 0.023(2) 0.009(2) C10 0.060(2) 0.077(3) 0.097(3) 0.017(2) 0.014(2) 0.0036(19) C11 0.063(2) 0.070(2) 0.067(2) 0.0093(17) -0.0064(17) -0.0149(17) C12 0.065(2) 0.0502(18) 0.0537(17) -0.0007(14) 0.0013(15) -0.0095(15) C13 0.073(2) 0.0489(18) 0.060(2) -0.0026(15) 0.0140(17) 0.0106(16) C14 0.093(3) 0.056(2) 0.080(2) -0.0027(18) 0.007(2) 0.0172(19) C15 0.051(2) 0.0579(19) 0.070(2) 0.0096(16) 0.0111(16) 0.0113(16) C16 0.060(2) 0.112(3) 0.107(3) 0.021(3) 0.011(2) 0.025(2) C17 0.049(2) 0.070(2) 0.081(2) 0.0066(19) 0.0121(17) -0.0058(17) C18 0.074(3) 0.126(4) 0.116(4) -0.028(3) 0.008(2) -0.043(3) C19 0.060(2) 0.0487(18) 0.0422(15) -0.0028(12) 0.0043(13) 0.0031(14) C20 0.078(2) 0.0404(17) 0.073(2) -0.0009(15) 0.0137(18) 0.0000(15) O1 0.0521(13) 0.0468(12) 0.0583(12) 0.0153(9) 0.0009(9) -0.0067(9) O2 0.0575(12) 0.0434(11) 0.0433(10) 0.0096(8) 0.0054(9) -0.0028(9) O3 0.0840(16) 0.0422(12) 0.0577(11) 0.0057(10) 0.0233(10) 0.0116(11) O4 0.228(4) 0.0672(18) 0.100(2) 0.0045(16) 0.092(3) 0.033(2) O5 0.0484(13) 0.0678(13) 0.0607(12) 0.0140(11) 0.0175(10) 0.0130(10) O6 0.0648(16) 0.0988(19) 0.0699(14) 0.0315(14) 0.0134(12) 0.0172(13) O7 0.0470(12) 0.0579(13) 0.0581(12) -0.0063(10) 0.0095(9) -0.0040(10) O8 0.0575(16) 0.0978(19) 0.104(2) -0.0036(16) 0.0324(15) -0.0097(13) O9 0.0569(12) 0.0381(10) 0.0436(10) 0.0014(8) 0.0143(8) -0.0011(9) O10 0.161(3) 0.0763(18) 0.0554(14) 0.0087(12) 0.0421(16) 0.0438(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.420(4) . ? C1 C2 1.519(4) . ? C1 C6 1.532(4) . ? C1 H1 0.9800 . ? C2 O2 1.419(3) . ? C2 C3 1.510(4) . ? C2 H2 0.9800 . ? C3 O3 1.446(3) . ? C3 C4 1.509(4) . ? C3 H3 0.9800 . ? C4 O5 1.426(3) . ? C4 C5 1.535(4) . ? C4 H4 0.9800 . ? C5 O7 1.426(4) . ? C5 C6 1.509(4) . ? C5 H5 0.9800 . ? C6 O9 1.443(3) . ? C6 H6 0.9800 . ? C7 O2 1.422(3) . ? C7 O1 1.457(3) . ? C7 C12 1.500(4) . ? C7 C8 1.500(4) . ? C8 C9 1.532(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.521(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.502(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.513(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O4 1.188(4) . ? C13 O3 1.335(4) . ? C13 C14 1.476(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O6 1.196(4) . ? C15 O5 1.356(4) . ? C15 C16 1.476(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O8 1.199(4) . ? C17 O7 1.362(4) . ? C17 C18 1.479(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O10 1.184(4) . ? C19 O9 1.345(4) . ? C19 C20 1.482(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 103.1(2) . . ? O1 C1 C6 110.0(2) . . ? C2 C1 C6 115.3(2) . . ? O1 C1 H1 109.4 . . ? C2 C1 H1 109.4 . . ? C6 C1 H1 109.4 . . ? O2 C2 C3 111.6(2) . . ? O2 C2 C1 101.6(2) . . ? C3 C2 C1 114.6(2) . . ? O2 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? O3 C3 C4 109.6(2) . . ? O3 C3 C2 109.6(2) . . ? C4 C3 C2 111.6(2) . . ? O3 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? O5 C4 C3 109.4(2) . . ? O5 C4 C5 109.0(2) . . ? C3 C4 C5 107.4(2) . . ? O5 C4 H4 110.3 . . ? C3 C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? O7 C5 C6 107.9(2) . . ? O7 C5 C4 110.6(2) . . ? C6 C5 C4 108.7(2) . . ? O7 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? O9 C6 C5 108.7(2) . . ? O9 C6 C1 107.4(2) . . ? C5 C6 C1 113.4(2) . . ? O9 C6 H6 109.1 . . ? C5 C6 H6 109.1 . . ? C1 C6 H6 109.1 . . ? O2 C7 O1 105.0(2) . . ? O2 C7 C12 111.9(2) . . ? O1 C7 C12 109.0(2) . . ? O2 C7 C8 108.8(2) . . ? O1 C7 C8 110.4(2) . . ? C12 C7 C8 111.5(3) . . ? C7 C8 C9 111.8(3) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 111.0(3) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 110.4(3) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 111.1(3) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C7 C12 C11 112.2(3) . . ? C7 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C7 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O4 C13 O3 121.8(3) . . ? O4 C13 C14 125.2(3) . . ? O3 C13 C14 113.0(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O6 C15 O5 123.3(3) . . ? O6 C15 C16 125.3(3) . . ? O5 C15 C16 111.4(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O8 C17 O7 122.5(3) . . ? O8 C17 C18 127.1(3) . . ? O7 C17 C18 110.4(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O10 C19 O9 123.0(3) . . ? O10 C19 C20 125.4(3) . . ? O9 C19 C20 111.6(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 O1 C7 108.3(2) . . ? C2 O2 C7 105.75(19) . . ? C13 O3 C3 117.6(2) . . ? C15 O5 C4 117.3(2) . . ? C17 O7 C5 117.8(2) . . ? C19 O9 C6 119.5(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 O1 C1 C2 O2 35.2(3) . . . . ? C6 C1 C2 O2 -84.8(3) . . . . ? O1 C1 C2 C3 155.6(2) . . . . ? C6 C1 C2 C3 35.7(3) . . . . ? O2 C2 C3 O3 -54.7(3) . . . . ? C1 C2 C3 O3 -169.5(2) . . . . ? O2 C2 C3 C4 66.9(3) . . . . ? C1 C2 C3 C4 -47.8(3) . . . . ? O3 C3 C4 O5 -57.3(3) . . . . ? C2 C3 C4 O5 -178.9(2) . . . . ? O3 C3 C4 C5 -175.5(2) . . . . ? C2 C3 C4 C5 62.9(3) . . . . ? O5 C4 C5 O7 56.9(3) . . . . ? C3 C4 C5 O7 175.3(2) . . . . ? O5 C4 C5 C6 175.1(2) . . . . ? C3 C4 C5 C6 -66.4(3) . . . . ? O7 C5 C6 O9 -65.4(2) . . . . ? C4 C5 C6 O9 174.6(2) . . . . ? O7 C5 C6 C1 175.2(2) . . . . ? C4 C5 C6 C1 55.2(3) . . . . ? O1 C1 C6 O9 83.8(2) . . . . ? C2 C1 C6 O9 -160.2(2) . . . . ? O1 C1 C6 C5 -156.1(2) . . . . ? C2 C1 C6 C5 -40.1(3) . . . . ? O2 C7 C8 C9 177.1(2) . . . . ? O1 C7 C8 C9 -68.1(3) . . . . ? C12 C7 C8 C9 53.2(3) . . . . ? C7 C8 C9 C10 -54.4(4) . . . . ? C8 C9 C10 C11 56.0(4) . . . . ? C9 C10 C11 C12 -56.7(4) . . . . ? O2 C7 C12 C11 -176.3(2) . . . . ? O1 C7 C12 C11 68.0(3) . . . . ? C8 C7 C12 C11 -54.2(3) . . . . ? C10 C11 C12 C7 56.2(4) . . . . ? C2 C1 O1 C7 -17.4(3) . . . . ? C6 C1 O1 C7 106.1(2) . . . . ? O2 C7 O1 C1 -6.7(3) . . . . ? C12 C7 O1 C1 113.3(3) . . . . ? C8 C7 O1 C1 -123.9(2) . . . . ? C3 C2 O2 C7 -163.0(2) . . . . ? C1 C2 O2 C7 -40.4(2) . . . . ? O1 C7 O2 C2 30.3(2) . . . . ? C12 C7 O2 C2 -87.9(3) . . . . ? C8 C7 O2 C2 148.4(2) . . . . ? O4 C13 O3 C3 3.7(5) . . . . ? C14 C13 O3 C3 -179.2(3) . . . . ? C4 C3 O3 C13 128.0(3) . . . . ? C2 C3 O3 C13 -109.2(3) . . . . ? O6 C15 O5 C4 -0.7(5) . . . . ? C16 C15 O5 C4 -179.6(3) . . . . ? C3 C4 O5 C15 109.8(3) . . . . ? C5 C4 O5 C15 -133.0(3) . . . . ? O8 C17 O7 C5 1.6(5) . . . . ? C18 C17 O7 C5 -177.4(3) . . . . ? C6 C5 O7 C17 141.1(3) . . . . ? C4 C5 O7 C17 -100.2(3) . . . . ? O10 C19 O9 C6 3.0(5) . . . . ? C20 C19 O9 C6 -178.3(2) . . . . ? C5 C6 O9 C19 117.1(3) . . . . ? C1 C6 O9 C19 -119.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 925398' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_kmsa73nm #TrackingRef 'web_deposit_cif_file_2_KanaM.Sureshan_1361278898.Kmsa73nm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 O8' _chemical_formula_weight 481.50 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 Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.298(4) _cell_length_b 11.735(5) _cell_length_c 22.178(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2680.2(18) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1794 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.82 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9965 _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APES CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10609 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 23.00 _reflns_number_total 3318 _reflns_number_gt 2798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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^)+(0.0739P)^2^+4.9991P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(4) _refine_ls_number_reflns 3318 _refine_ls_number_parameters 284 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.1150 _refine_ls_wR_factor_ref 0.2409 _refine_ls_wR_factor_gt 0.2318 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _refine_ls_shift/su_max 0.006 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O8 O 0.2005(4) 0.0136(4) 0.3844(2) 0.0460(14) Uani 1 d . . . O1 O 0.2785(5) -0.0189(5) 0.5036(3) 0.0512(15) Uani 1 d . . . O2 O 0.4626(5) 0.0320(6) 0.5536(3) 0.0645(18) Uani 1 d . . . O3 O 0.5012(6) 0.2828(5) 0.5362(3) 0.082(2) Uani 1 d . . . O4 O 0.2994(5) 0.3737(5) 0.4677(4) 0.073(2) Uani 1 d . . . O5 O 0.4232(10) 0.4647(7) 0.4003(6) 0.142(4) Uani 1 d . . . O6 O 0.2017(5) 0.2487(5) 0.3716(3) 0.0570(16) Uani 1 d . . . O7 O -0.0034(6) 0.2399(6) 0.4034(4) 0.081(2) Uani 1 d . . . C1 C 0.3741(7) 0.0217(6) 0.4611(4) 0.0381(18) Uiso 1 d . . . H1 H 0.4252 -0.0431 0.4465 0.046 Uiso 1 calc R . . C2 C 0.4581(8) 0.0953(7) 0.4987(5) 0.053(2) Uani 1 d . . . H2 H 0.5451 0.1003 0.4810 0.063 Uiso 1 calc R . . C3 C 0.4056(8) 0.2130(9) 0.5108(5) 0.065(3) Uani 1 d . . . H3 H 0.3345 0.2060 0.5399 0.078 Uiso 1 calc R . . C5 C 0.2513(7) 0.1934(7) 0.4258(4) 0.045(2) Uani 1 d . . . H5 H 0.1801 0.1832 0.4547 0.053 Uiso 1 calc R . . C4 C 0.3499(9) 0.2661(7) 0.4523(5) 0.062(3) Uani 1 d . . . H4 H 0.4206 0.2762 0.4232 0.075 Uiso 1 calc R . . C6 C 0.3044(6) 0.0771(6) 0.4076(4) 0.041(2) Uani 1 d . . . H6 H 0.3679 0.0883 0.3752 0.049 Uiso 1 calc R . . C7 C 0.3507(8) -0.0397(8) 0.5556(5) 0.060(3) Uani 1 d . . . C8 C 0.3966(10) -0.1625(9) 0.5591(6) 0.086(3) Uani 1 d . . . H8A H 0.4483 -0.1728 0.5947 0.130 Uiso 1 calc R . . H8B H 0.4478 -0.1801 0.5241 0.130 Uiso 1 calc R . . H8C H 0.3228 -0.2123 0.5607 0.130 Uiso 1 calc R . . C9 C 0.2626(11) -0.0076(11) 0.6098(5) 0.100(4) Uani 1 d . . . H9A H 0.3102 -0.0173 0.6467 0.150 Uiso 1 calc R . . H9B H 0.1876 -0.0561 0.6102 0.150 Uiso 1 calc R . . H9C H 0.2357 0.0704 0.6061 0.150 Uiso 1 calc R . . C10A C 0.503(2) 0.2710(19) 0.6051(12) 0.082(6) Uiso 0.50 d P . . C10 C 0.468(4) 0.371(3) 0.574(2) 0.156(13) Uiso 0.50 d P . . C11 C 0.5792(12) 0.3718(11) 0.6250(6) 0.090(4) Uiso 1 d . . . C12 C 0.5633(19) 0.4717(17) 0.6091(9) 0.149(6) Uiso 1 d . . . C13 C 0.6285(19) 0.5571(18) 0.6299(10) 0.168(7) Uiso 1 d . . . H13 H 0.6154 0.6308 0.6157 0.202 Uiso 1 calc R . . C14 C 0.7217(16) 0.5325(13) 0.6757(8) 0.133(5) Uiso 1 d . . . H14 H 0.7667 0.5935 0.6924 0.159 Uiso 1 calc R . . C15 C 0.7477(15) 0.4340(13) 0.6952(8) 0.124(5) Uiso 1 d . . . H15 H 0.8113 0.4233 0.7244 0.148 Uiso 1 calc R . . C16 C 0.6757(15) 0.3373(14) 0.6709(8) 0.137(5) Uiso 1 d . . . H16 H 0.6889 0.2623 0.6830 0.164 Uiso 1 calc R . . C17 C 0.3364(11) 0.4655(9) 0.4372(8) 0.102(5) Uani 1 d . . . C18 C 0.2637(13) 0.5699(9) 0.4566(9) 0.131(6) Uani 1 d . . . H18A H 0.2886 0.5898 0.4969 0.197 Uiso 1 calc R . . H18B H 0.1721 0.5549 0.4553 0.197 Uiso 1 calc R . . H18C H 0.2839 0.6318 0.4299 0.197 Uiso 1 calc R . . C19 C 0.0767(9) 0.2676(7) 0.3674(5) 0.057(2) Uani 1 d . . . C20 C 0.0481(12) 0.3272(12) 0.3077(7) 0.120(5) Uani 1 d . . . H20A H -0.0368 0.3609 0.3092 0.180 Uiso 1 calc R . . H20B H 0.0514 0.2726 0.2755 0.180 Uiso 1 calc R . . H20C H 0.1117 0.3856 0.3008 0.180 Uiso 1 calc R . . C21 C 0.2371(9) -0.0819(8) 0.3528(4) 0.059(2) Uani 1 d . . . H21A H 0.2582 -0.1428 0.3807 0.070 Uiso 1 calc R . . H21B H 0.3139 -0.0653 0.3291 0.070 Uiso 1 calc R . . C22 C 0.1289(9) -0.1189(7) 0.3121(4) 0.055(2) Uani 1 d . . . C23 C 0.0784(11) -0.2274(9) 0.3138(5) 0.079(3) Uani 1 d . . . H23 H 0.1123 -0.2824 0.3396 0.095 Uiso 1 calc R . . C24 C -0.0252(12) -0.2520(12) 0.2756(8) 0.098(5) Uani 1 d . . . H24 H -0.0612 -0.3246 0.2768 0.118 Uiso 1 calc R . . C25 C -0.0764(14) -0.1736(17) 0.2364(6) 0.109(5) Uani 1 d . . . H25 H -0.1450 -0.1920 0.2110 0.131 Uiso 1 calc R . . C26 C -0.0239(13) -0.0701(13) 0.2363(5) 0.098(4) Uani 1 d . . . H26 H -0.0564 -0.0154 0.2100 0.117 Uiso 1 calc R . . C27 C 0.0764(11) -0.0417(9) 0.2739(5) 0.070(3) Uani 1 d . . . H27 H 0.1092 0.0322 0.2731 0.083 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 O8 0.030(3) 0.064(3) 0.044(4) -0.016(3) 0.002(3) -0.005(3) O1 0.022(3) 0.081(4) 0.051(4) -0.003(3) -0.008(3) -0.006(3) O2 0.032(3) 0.100(5) 0.062(5) -0.013(4) -0.010(3) -0.003(3) O3 0.063(4) 0.074(4) 0.110(6) -0.066(4) -0.009(4) -0.012(4) O4 0.052(4) 0.060(4) 0.106(6) -0.008(4) 0.014(4) -0.007(3) O5 0.128(8) 0.078(5) 0.218(13) 0.012(6) 0.064(9) -0.016(5) O6 0.042(4) 0.075(4) 0.055(4) 0.010(3) 0.008(3) 0.005(3) O7 0.043(4) 0.094(5) 0.107(7) 0.021(5) 0.003(4) -0.002(3) C2 0.031(5) 0.071(6) 0.057(7) -0.015(5) 0.006(4) 0.005(4) C3 0.029(5) 0.105(8) 0.059(7) -0.038(6) -0.001(5) -0.018(5) C5 0.025(4) 0.056(5) 0.053(6) -0.012(4) 0.016(4) -0.009(3) C4 0.047(5) 0.062(6) 0.079(8) -0.028(5) 0.014(5) 0.004(5) C6 0.017(4) 0.049(4) 0.056(6) -0.010(4) 0.014(4) -0.007(3) C7 0.032(5) 0.092(7) 0.055(6) 0.001(5) -0.011(5) 0.001(5) C8 0.096(8) 0.089(8) 0.074(8) 0.022(6) -0.019(7) -0.001(6) C9 0.068(8) 0.176(12) 0.056(7) -0.004(8) 0.012(6) 0.011(8) C17 0.057(8) 0.059(7) 0.191(16) -0.025(8) 0.012(8) -0.022(6) C18 0.106(9) 0.049(6) 0.238(19) -0.009(9) 0.012(11) -0.019(7) C19 0.044(6) 0.054(5) 0.072(7) 0.008(5) 0.003(5) 0.003(4) C20 0.085(9) 0.111(10) 0.163(16) 0.037(10) -0.036(10) 0.011(7) C21 0.063(6) 0.076(6) 0.037(6) -0.025(5) 0.004(5) 0.007(5) C22 0.079(7) 0.044(5) 0.040(6) -0.021(4) -0.001(5) 0.006(5) C23 0.079(8) 0.078(7) 0.081(9) -0.038(6) 0.017(7) 0.007(6) C24 0.072(8) 0.103(10) 0.121(13) -0.061(9) 0.007(9) -0.035(7) C25 0.100(10) 0.171(15) 0.056(9) -0.069(10) -0.030(8) -0.010(11) C26 0.125(11) 0.130(11) 0.039(7) -0.034(7) -0.027(7) -0.015(9) C27 0.082(7) 0.070(7) 0.056(7) -0.024(6) 0.005(6) -0.030(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 O8 C21 1.374(9) . ? O8 C6 1.401(8) . ? O1 C7 1.394(11) . ? O1 C1 1.443(9) . ? O2 C7 1.428(10) . ? O2 C2 1.426(11) . ? O3 C10 1.37(4) . ? O3 C3 1.399(9) . ? O3 C10A 1.53(3) . ? O4 C17 1.328(15) . ? O4 C4 1.408(10) . ? O5 C17 1.212(15) . ? O6 C19 1.310(10) . ? O6 C5 1.459(10) . ? O7 C19 1.194(10) . ? C1 C2 1.479(11) . ? C1 C6 1.531(11) . ? C1 H1 0.9800 . ? C2 C3 1.507(12) . ? C2 H2 0.9800 . ? C3 C4 1.548(14) . ? C3 H3 0.9800 . ? C5 C4 1.451(11) . ? C5 C6 1.526(10) . ? C5 H5 0.9800 . ? C4 H4 0.9800 . ? C6 H6 0.9800 . ? C7 C8 1.519(13) . ? C7 C9 1.552(14) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10A C10 1.41(4) . ? C10A C11 1.49(2) . ? C10 C11 1.61(4) . ? C11 C12 1.235(19) . ? C11 C16 1.481(19) . ? C12 C13 1.29(2) . ? C13 C14 1.43(2) . ? C13 H13 0.9300 . ? C14 C15 1.263(18) . ? C14 H14 0.9300 . ? C15 C16 1.458(19) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.499(16) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.527(15) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.499(12) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.355(13) . ? C22 C23 1.376(13) . ? C23 C24 1.392(17) . ? C23 H23 0.9300 . ? C24 C25 1.372(19) . ? C24 H24 0.9300 . ? C25 C26 1.329(19) . ? C25 H25 0.9300 . ? C26 C27 1.368(15) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 O8 C6 114.2(6) . . ? C7 O1 C1 103.5(5) . . ? C7 O2 C2 107.9(6) . . ? C10 O3 C3 120.7(17) . . ? C10 O3 C10A 57.7(19) . . ? C3 O3 C10A 110.9(11) . . ? C17 O4 C4 119.9(9) . . ? C19 O6 C5 118.5(7) . . ? O1 C1 C2 103.0(7) . . ? O1 C1 C6 109.0(6) . . ? C2 C1 C6 117.6(6) . . ? O1 C1 H1 108.9 . . ? C2 C1 H1 108.9 . . ? C6 C1 H1 108.9 . . ? O2 C2 C1 101.3(7) . . ? O2 C2 C3 109.7(8) . . ? C1 C2 C3 115.1(7) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C2 110.9(7) . . ? O3 C3 C4 111.3(9) . . ? C2 C3 C4 110.7(7) . . ? O3 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? C4 C5 O6 108.5(7) . . ? C4 C5 C6 112.4(7) . . ? O6 C5 C6 107.8(7) . . ? C4 C5 H5 109.3 . . ? O6 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? O4 C4 C5 111.5(7) . . ? O4 C4 C3 107.2(8) . . ? C5 C4 C3 111.2(8) . . ? O4 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? O8 C6 C5 107.4(5) . . ? O8 C6 C1 114.7(6) . . ? C5 C6 C1 110.0(7) . . ? O8 C6 H6 108.2 . . ? C5 C6 H6 108.2 . . ? C1 C6 H6 108.2 . . ? O1 C7 O2 107.6(7) . . ? O1 C7 C8 111.9(8) . . ? O2 C7 C8 108.0(7) . . ? O1 C7 C9 106.7(7) . . ? O2 C7 C9 110.7(8) . . ? C8 C7 C9 111.9(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 C10A C11 67.6(19) . . ? C10 C10A O3 55(2) . . ? C11 C10A O3 103.2(15) . . ? C10A C10 O3 67(2) . . ? C10A C10 C11 58.5(19) . . ? O3 C10 C11 105(2) . . ? C12 C11 C16 123.0(15) . . ? C12 C11 C10A 126.9(17) . . ? C16 C11 C10A 110.0(14) . . ? C12 C11 C10 73.2(17) . . ? C16 C11 C10 163.8(19) . . ? C10A C11 C10 53.9(16) . . ? C11 C12 C13 125(2) . . ? C12 C13 C14 117(2) . . ? C12 C13 H13 121.7 . . ? C14 C13 H13 121.7 . . ? C15 C14 C13 124.9(18) . . ? C15 C14 H14 117.6 . . ? C13 C14 H14 117.6 . . ? C14 C15 C16 118.5(17) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C11 112.5(13) . . ? C15 C16 H16 123.7 . . ? C11 C16 H16 123.7 . . ? O5 C17 O4 123.3(11) . . ? O5 C17 C18 124.6(13) . . ? O4 C17 C18 111.9(13) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O7 C19 O6 125.9(9) . . ? O7 C19 C20 124.9(9) . . ? O6 C19 C20 109.2(9) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O8 C21 C22 109.9(7) . . ? O8 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? O8 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C27 C22 C23 119.0(9) . . ? C27 C22 C21 118.7(8) . . ? C23 C22 C21 122.2(10) . . ? C22 C23 C24 117.7(12) . . ? C22 C23 H23 121.1 . . ? C24 C23 H23 121.1 . . ? C25 C24 C23 122.8(12) . . ? C25 C24 H24 118.6 . . ? C23 C24 H24 118.6 . . ? C26 C25 C24 117.2(12) . . ? C26 C25 H25 121.4 . . ? C24 C25 H25 121.4 . . ? C25 C26 C27 121.9(13) . . ? C25 C26 H26 119.0 . . ? C27 C26 H26 119.0 . . ? C22 C27 C26 121.3(10) . . ? C22 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.384 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 925399'