# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_ritmc01 _database_code_depnum_ccdc_archive 'CCDC 889654' #TrackingRef 'web_deposit_cif_file_0_WilliamW.Brennessel_1341257024.ritmc01.cif' _vrf_DIFMX01_ritmc01 ; PROBLEM: _C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.641 Test value = 0.600 RESPONSE: The largest peaks of residual electron density are found in the bonds between atoms. ; _vrf_DIFMX02_ritmc01 ; PROBLEM: _C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RESPONSE: See above. ; _vrf_PLAT094_ritmc01 ; PROBLEM: _C Ratio of Maximum / Minimum Residual Density .... 3.17 RESPONSE: See above. ; _vrf_PLAT097_ritmc01 ; PROBLEM: _C Large Reported Max. (Positive) Residual Density .. 0.64 eA-3 RESPONSE: See above. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ritmc01 _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O4' _chemical_formula_sum 'C15 H16 O4' _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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 9.1969(10) _cell_length_b 11.1313(12) _cell_length_c 12.8767(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.477(2) _cell_angle_gamma 90.00 _cell_volume 1296.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 3958 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 37.83 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46703 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 37.78 _reflns_number_total 6902 _reflns_number_gt 5431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0716P)^2^+0.1872P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6902 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.75305(5) 0.24457(4) 0.36846(4) 0.01559(9) Uani 1 1 d . . . O2 O 0.28784(6) 0.09712(5) -0.04142(4) 0.02087(10) Uani 1 1 d . . . O3 O 1.00286(8) 0.14126(6) 0.66435(5) 0.02967(14) Uani 1 1 d . . . O4 O 0.88385(6) -0.03364(5) 0.62665(4) 0.02114(10) Uani 1 1 d . . . C1 C 0.84666(7) 0.23286(6) 0.46227(5) 0.01531(10) Uani 1 1 d . . . C2 C 0.82816(7) 0.12208(6) 0.50449(5) 0.01498(10) Uani 1 1 d . . . C3 C 0.71558(7) 0.05968(6) 0.43059(5) 0.01491(10) Uani 1 1 d . . . C4 C 0.67293(7) 0.13866(5) 0.34980(5) 0.01437(10) Uani 1 1 d . . . C5 C 0.94378(9) 0.33704(7) 0.49652(6) 0.02178(13) Uani 1 1 d . . . H5A H 0.9818(16) 0.3669(13) 0.4367(12) 0.038(4) Uiso 1 1 d . . . H5B H 1.0280(16) 0.3119(13) 0.5507(11) 0.037(3) Uiso 1 1 d . . . H5C H 0.8883(15) 0.4018(13) 0.5230(11) 0.038(3) Uiso 1 1 d . . . C6 C 0.66323(9) -0.06700(6) 0.43606(6) 0.02004(12) Uani 1 1 d . . . H6A H 0.6012(14) -0.0920(12) 0.3678(10) 0.030(3) Uiso 1 1 d . . . H6B H 0.6031(15) -0.0791(13) 0.4910(11) 0.038(3) Uiso 1 1 d . . . H6C H 0.7446(16) -0.1215(13) 0.4515(10) 0.035(3) Uiso 1 1 d . . . C7 C 0.57226(7) 0.13152(6) 0.24829(5) 0.01463(10) Uani 1 1 d . . . C8 C 0.43568(8) 0.07228(7) 0.23777(5) 0.01857(12) Uani 1 1 d . . . H8 H 0.4038(13) 0.0368(11) 0.2995(10) 0.024(3) Uiso 1 1 d . . . C9 C 0.34471(8) 0.06180(7) 0.14016(6) 0.01952(12) Uani 1 1 d . . . H9 H 0.2506(14) 0.0198(12) 0.1341(10) 0.029(3) Uiso 1 1 d . . . C10 C 0.38649(7) 0.11145(6) 0.05023(5) 0.01600(11) Uani 1 1 d . . . C11 C 0.52126(7) 0.17166(6) 0.05934(5) 0.01613(11) Uani 1 1 d . . . H11 H 0.5554(12) 0.2061(11) -0.0023(9) 0.020(2) Uiso 1 1 d . . . C12 C 0.61247(7) 0.18098(6) 0.15778(5) 0.01551(10) Uani 1 1 d . . . H12 H 0.7046(13) 0.2234(11) 0.1625(9) 0.024(3) Uiso 1 1 d . . . C13 C 0.32262(9) 0.15146(7) -0.13436(6) 0.02319(14) Uani 1 1 d . . . H13A H 0.2403(15) 0.1323(12) -0.1896(11) 0.032(3) Uiso 1 1 d . . . H13B H 0.4157(14) 0.1200(12) -0.1499(10) 0.029(3) Uiso 1 1 d . . . H13C H 0.3317(14) 0.2393(12) -0.1264(10) 0.032(3) Uiso 1 1 d . . . C14 C 0.91402(7) 0.08071(6) 0.60545(5) 0.01702(11) Uani 1 1 d . . . C15 C 0.97115(9) -0.08172(8) 0.72192(6) 0.02432(14) Uani 1 1 d . . . H15A H 0.9360(17) -0.1619(14) 0.7289(12) 0.045(4) Uiso 1 1 d . . . H15B H 0.9573(15) -0.0325(13) 0.7835(12) 0.038(3) Uiso 1 1 d . . . H15C H 1.0762(15) -0.0813(12) 0.7163(11) 0.033(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0167(2) 0.01440(18) 0.01463(19) 0.00011(14) 0.00007(15) -0.00192(14) O2 0.0177(2) 0.0269(2) 0.0159(2) -0.00171(17) -0.00236(17) -0.00094(18) O3 0.0365(3) 0.0233(3) 0.0228(3) -0.00031(19) -0.0114(2) -0.0037(2) O4 0.0225(2) 0.0201(2) 0.0189(2) 0.00547(17) -0.00130(18) -0.00098(18) C1 0.0153(2) 0.0152(2) 0.0145(2) -0.00090(17) 0.00022(19) -0.00069(18) C2 0.0163(2) 0.0147(2) 0.0133(2) -0.00037(17) 0.00098(19) 0.00033(18) C3 0.0167(2) 0.0145(2) 0.0134(2) -0.00027(17) 0.00228(19) -0.00127(18) C4 0.0153(2) 0.0144(2) 0.0131(2) -0.00069(17) 0.00166(18) -0.00203(18) C5 0.0212(3) 0.0178(3) 0.0236(3) -0.0004(2) -0.0031(2) -0.0053(2) C6 0.0253(3) 0.0157(2) 0.0183(3) 0.0007(2) 0.0016(2) -0.0045(2) C7 0.0146(2) 0.0155(2) 0.0134(2) -0.00083(17) 0.00165(18) -0.00076(18) C8 0.0170(3) 0.0236(3) 0.0153(2) -0.0011(2) 0.0034(2) -0.0045(2) C9 0.0151(3) 0.0255(3) 0.0176(3) -0.0019(2) 0.0018(2) -0.0045(2) C10 0.0147(2) 0.0175(2) 0.0148(2) -0.00234(18) 0.00006(19) 0.00112(19) C11 0.0158(2) 0.0176(2) 0.0144(2) 0.00076(18) 0.00128(19) 0.00021(19) C12 0.0145(2) 0.0169(2) 0.0145(2) 0.00092(18) 0.00098(19) -0.00137(18) C13 0.0245(3) 0.0279(3) 0.0152(3) -0.0011(2) -0.0015(2) 0.0024(3) C14 0.0181(3) 0.0176(2) 0.0148(2) -0.00020(19) 0.0013(2) 0.0019(2) C15 0.0241(3) 0.0282(3) 0.0197(3) 0.0082(2) 0.0012(2) 0.0048(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 O1 C1 1.3562(8) . ? O1 C4 1.3879(8) . ? O2 C10 1.3609(8) . ? O2 C13 1.4281(10) . ? O3 C14 1.2132(9) . ? O4 C14 1.3414(9) . ? O4 C15 1.4414(9) . ? C1 C2 1.3707(9) . ? C1 C5 1.4812(9) . ? C2 C3 1.4497(9) . ? C2 C14 1.4671(9) . ? C3 C4 1.3640(9) . ? C3 C6 1.4959(9) . ? C4 C7 1.4601(9) . ? C5 H5A 0.961(15) . ? C5 H5B 0.984(14) . ? C5 H5C 0.980(15) . ? C6 H6A 0.997(13) . ? C6 H6B 0.984(14) . ? C6 H6C 0.956(14) . ? C7 C12 1.3982(9) . ? C7 C8 1.4033(9) . ? C8 C9 1.3824(10) . ? C8 H8 0.979(12) . ? C9 C10 1.3986(10) . ? C9 H9 0.974(13) . ? C10 C11 1.3951(9) . ? C11 C12 1.3908(9) . ? C11 H11 0.982(11) . ? C12 H12 0.962(12) . ? C13 H13A 0.964(14) . ? C13 H13B 0.979(13) . ? C13 H13C 0.985(14) . ? C15 H15A 0.959(16) . ? C15 H15B 0.991(15) . ? C15 H15C 0.982(14) . ? 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 O1 C4 107.67(5) . . ? C10 O2 C13 117.48(6) . . ? C14 O4 C15 114.94(6) . . ? O1 C1 C2 109.59(5) . . ? O1 C1 C5 116.15(6) . . ? C2 C1 C5 134.26(6) . . ? C1 C2 C3 107.22(5) . . ? C1 C2 C14 123.24(6) . . ? C3 C2 C14 129.52(6) . . ? C4 C3 C2 105.30(5) . . ? C4 C3 C6 126.38(6) . . ? C2 C3 C6 128.19(6) . . ? C3 C4 O1 110.21(5) . . ? C3 C4 C7 134.05(6) . . ? O1 C4 C7 115.56(5) . . ? C1 C5 H5A 108.6(9) . . ? C1 C5 H5B 110.0(9) . . ? H5A C5 H5B 108.2(12) . . ? C1 C5 H5C 110.8(8) . . ? H5A C5 H5C 108.3(12) . . ? H5B C5 H5C 110.8(12) . . ? C3 C6 H6A 111.1(8) . . ? C3 C6 H6B 113.0(8) . . ? H6A C6 H6B 106.9(11) . . ? C3 C6 H6C 111.2(8) . . ? H6A C6 H6C 107.9(11) . . ? H6B C6 H6C 106.6(11) . . ? C12 C7 C8 118.19(6) . . ? C12 C7 C4 120.27(6) . . ? C8 C7 C4 121.51(6) . . ? C9 C8 C7 120.70(6) . . ? C9 C8 H8 118.9(7) . . ? C7 C8 H8 120.4(7) . . ? C8 C9 C10 120.50(6) . . ? C8 C9 H9 119.7(8) . . ? C10 C9 H9 119.8(8) . . ? O2 C10 C11 124.84(6) . . ? O2 C10 C9 115.56(6) . . ? C11 C10 C9 119.59(6) . . ? C12 C11 C10 119.47(6) . . ? C12 C11 H11 118.6(7) . . ? C10 C11 H11 121.9(7) . . ? C11 C12 C7 121.55(6) . . ? C11 C12 H12 118.2(7) . . ? C7 C12 H12 120.2(7) . . ? O2 C13 H13A 105.0(8) . . ? O2 C13 H13B 111.0(8) . . ? H13A C13 H13B 111.6(11) . . ? O2 C13 H13C 111.2(8) . . ? H13A C13 H13C 109.7(10) . . ? H13B C13 H13C 108.4(10) . . ? O3 C14 O4 122.73(6) . . ? O3 C14 C2 124.92(6) . . ? O4 C14 C2 112.35(6) . . ? O4 C15 H15A 106.3(9) . . ? O4 C15 H15B 110.1(8) . . ? H15A C15 H15B 110.1(12) . . ? O4 C15 H15C 109.8(8) . . ? H15A C15 H15C 111.3(12) . . ? H15B C15 H15C 109.1(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 C4 O1 C1 C2 -0.22(7) . . . . ? C4 O1 C1 C5 179.58(6) . . . . ? O1 C1 C2 C3 0.69(7) . . . . ? C5 C1 C2 C3 -179.05(7) . . . . ? O1 C1 C2 C14 179.44(6) . . . . ? C5 C1 C2 C14 -0.31(12) . . . . ? C1 C2 C3 C4 -0.90(7) . . . . ? C14 C2 C3 C4 -179.54(6) . . . . ? C1 C2 C3 C6 175.10(7) . . . . ? C14 C2 C3 C6 -3.54(11) . . . . ? C2 C3 C4 O1 0.78(7) . . . . ? C6 C3 C4 O1 -175.31(6) . . . . ? C2 C3 C4 C7 175.54(7) . . . . ? C6 C3 C4 C7 -0.55(12) . . . . ? C1 O1 C4 C3 -0.38(7) . . . . ? C1 O1 C4 C7 -176.21(5) . . . . ? C3 C4 C7 C12 -137.29(8) . . . . ? O1 C4 C7 C12 37.26(8) . . . . ? C3 C4 C7 C8 40.70(11) . . . . ? O1 C4 C7 C8 -144.76(6) . . . . ? C12 C7 C8 C9 0.93(10) . . . . ? C4 C7 C8 C9 -177.10(6) . . . . ? C7 C8 C9 C10 -0.80(11) . . . . ? C13 O2 C10 C11 -2.35(10) . . . . ? C13 O2 C10 C9 177.02(6) . . . . ? C8 C9 C10 O2 -179.21(7) . . . . ? C8 C9 C10 C11 0.18(11) . . . . ? O2 C10 C11 C12 179.61(6) . . . . ? C9 C10 C11 C12 0.28(10) . . . . ? C10 C11 C12 C7 -0.13(10) . . . . ? C8 C7 C12 C11 -0.47(10) . . . . ? C4 C7 C12 C11 177.58(6) . . . . ? C15 O4 C14 O3 -3.41(10) . . . . ? C15 O4 C14 C2 176.53(6) . . . . ? C1 C2 C14 O3 4.41(11) . . . . ? C3 C2 C14 O3 -177.15(7) . . . . ? C1 C2 C14 O4 -175.53(6) . . . . ? C3 C2 C14 O4 2.91(10) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.641 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.057 # Attachment 'web_deposit_cif_file_1_WilliamW.Brennessel_1341257024.ritmc04.cif' data_ritmc04 _database_code_depnum_ccdc_archive 'CCDC 889655' #TrackingRef 'web_deposit_cif_file_1_WilliamW.Brennessel_1341257024.ritmc04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ritmc04 _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O5' _chemical_formula_sum 'C15 H16 O5' _chemical_formula_weight 276.28 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0488(8) _cell_length_b 12.3096(12) _cell_length_c 14.1598(14) _cell_angle_alpha 104.845(2) _cell_angle_beta 101.999(2) _cell_angle_gamma 92.355(2) _cell_volume 1319.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 4054 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 36.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28517 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0853 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 34.97 _reflns_number_total 11431 _reflns_number_gt 6639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11431 _refine_ls_number_parameters 489 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1102 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.62001(13) 0.35511(8) -0.02041(7) 0.01685(19) Uani 1 1 d . . . O2 O 0.43718(14) 0.19518(8) -0.09576(7) 0.0211(2) Uani 1 1 d . . . O3 O 0.33784(14) 0.11342(9) 0.06615(8) 0.0259(2) Uani 1 1 d . . . O4 O 0.52763(14) 0.17968(9) 0.21301(8) 0.0219(2) Uani 1 1 d . . . O5 O 1.11764(14) 0.80865(8) 0.10791(8) 0.0209(2) Uani 1 1 d . . . C1 C 0.52609(17) 0.26666(11) -0.01271(10) 0.0159(2) Uani 1 1 d . . . C2 C 0.54601(18) 0.26418(11) 0.08537(10) 0.0155(2) Uani 1 1 d . . . C3 C 0.66506(18) 0.36199(11) 0.14387(10) 0.0155(2) Uani 1 1 d . . . C4 C 0.70671(18) 0.41432(11) 0.07710(10) 0.0157(2) Uani 1 1 d . . . C5 C 0.4299(2) 0.22709(13) -0.18824(11) 0.0237(3) Uani 1 1 d . . . H5A H 0.368(2) 0.1680(15) -0.2380(13) 0.023(4) Uiso 1 1 d . . . H5B H 0.546(3) 0.2384(16) -0.1976(14) 0.033(5) Uiso 1 1 d . . . H5C H 0.372(3) 0.2964(18) -0.1859(15) 0.040(6) Uiso 1 1 d . . . C6 C 0.45912(19) 0.17911(11) 0.11735(10) 0.0179(3) Uani 1 1 d . . . C7 C 0.4462(2) 0.09680(15) 0.24870(13) 0.0270(3) Uani 1 1 d . . . H7A H 0.509(3) 0.1045(16) 0.3149(16) 0.037(5) Uiso 1 1 d . . . H7B H 0.451(2) 0.0218(15) 0.2087(13) 0.024(5) Uiso 1 1 d . . . H7C H 0.325(3) 0.1099(15) 0.2476(13) 0.029(5) Uiso 1 1 d . . . C8 C 0.7230(2) 0.40118(12) 0.25551(10) 0.0200(3) Uani 1 1 d . . . H8A H 0.743(2) 0.4820(15) 0.2786(13) 0.025(5) Uiso 1 1 d . . . H8B H 0.829(3) 0.3657(17) 0.2798(15) 0.041(6) Uiso 1 1 d . . . H8C H 0.636(3) 0.3814(16) 0.2908(14) 0.035(5) Uiso 1 1 d . . . C9 C 0.81289(17) 0.51562(11) 0.08317(10) 0.0154(2) Uani 1 1 d . . . C10 C 0.95066(19) 0.56098(11) 0.16495(10) 0.0185(3) Uani 1 1 d . . . H10 H 0.981(2) 0.5210(15) 0.2165(14) 0.029(5) Uiso 1 1 d . . . C11 C 1.04904(19) 0.65833(12) 0.17109(11) 0.0197(3) Uani 1 1 d . . . H11 H 1.145(3) 0.6880(16) 0.2276(14) 0.034(5) Uiso 1 1 d . . . C12 C 1.01393(18) 0.71232(11) 0.09520(10) 0.0173(3) Uani 1 1 d . . . C13 C 0.88082(19) 0.66714(12) 0.01224(11) 0.0191(3) Uani 1 1 d . . . H13 H 0.856(2) 0.7035(13) -0.0414(12) 0.017(4) Uiso 1 1 d . . . C14 C 0.78158(19) 0.56994(11) 0.00718(10) 0.0180(3) Uani 1 1 d . . . H14 H 0.691(2) 0.5384(15) -0.0504(13) 0.025(5) Uiso 1 1 d . . . C15 C 1.1052(2) 0.85203(12) 0.02248(12) 0.0221(3) Uani 1 1 d . . . H15A H 1.193(3) 0.9176(16) 0.0430(14) 0.032(5) Uiso 1 1 d . . . H15B H 0.989(2) 0.8769(13) 0.0025(12) 0.016(4) Uiso 1 1 d . . . H15C H 1.128(2) 0.7944(15) -0.0360(13) 0.024(4) Uiso 1 1 d . . . O6 O -0.00818(13) 0.18834(8) 0.31208(7) 0.01669(19) Uani 1 1 d . . . O7 O -0.17661(14) 0.02104(8) 0.25676(7) 0.0211(2) Uani 1 1 d . . . O8 O -0.28572(14) -0.02604(8) 0.42628(8) 0.0227(2) Uani 1 1 d . . . O9 O -0.15561(13) 0.09203(8) 0.57541(7) 0.0196(2) Uani 1 1 d . . . O10 O 0.44891(15) 0.63781(9) 0.36237(8) 0.0259(2) Uani 1 1 d . . . C16 C -0.09997(18) 0.10708(11) 0.33192(10) 0.0163(2) Uani 1 1 d . . . C17 C -0.09277(18) 0.12756(11) 0.43237(10) 0.0163(2) Uani 1 1 d . . . C18 C 0.01979(18) 0.23154(11) 0.47987(10) 0.0155(2) Uani 1 1 d . . . C19 C 0.06455(18) 0.26695(11) 0.40406(10) 0.0159(2) Uani 1 1 d . . . C20 C -0.1561(2) 0.02390(14) 0.15830(11) 0.0243(3) Uani 1 1 d . . . H20A H -0.218(2) -0.0417(15) 0.1148(13) 0.024(4) Uiso 1 1 d . . . H20B H -0.036(2) 0.0249(14) 0.1574(12) 0.020(4) Uiso 1 1 d . . . H20C H -0.206(2) 0.0904(16) 0.1435(13) 0.027(5) Uiso 1 1 d . . . C21 C -0.18697(18) 0.05578(11) 0.47478(10) 0.0170(3) Uani 1 1 d . . . C22 C -0.2502(2) 0.02834(13) 0.62259(12) 0.0218(3) Uani 1 1 d . . . H22A H -0.208(2) 0.0611(15) 0.6934(14) 0.027(5) Uiso 1 1 d . . . H22B H -0.230(2) -0.0549(15) 0.6006(13) 0.027(5) Uiso 1 1 d . . . H22C H -0.371(2) 0.0341(15) 0.6018(13) 0.027(5) Uiso 1 1 d . . . C23 C 0.0784(2) 0.28553(12) 0.58976(10) 0.0197(3) Uani 1 1 d . . . H23A H 0.193(2) 0.3326(15) 0.6082(13) 0.025(5) Uiso 1 1 d . . . H23B H 0.096(2) 0.2281(16) 0.6273(14) 0.032(5) Uiso 1 1 d . . . H23C H -0.001(2) 0.3326(16) 0.6168(14) 0.033(5) Uiso 1 1 d . . . C24 C 0.16407(17) 0.36445(11) 0.39586(10) 0.0158(2) Uani 1 1 d . . . C25 C 0.20362(19) 0.46391(11) 0.47307(11) 0.0187(3) Uani 1 1 d . . . H25 H 0.161(2) 0.4728(14) 0.5337(12) 0.019(4) Uiso 1 1 d . . . C26 C 0.29925(19) 0.55671(12) 0.46562(11) 0.0197(3) Uani 1 1 d . . . H26 H 0.319(2) 0.6253(15) 0.5203(13) 0.023(4) Uiso 1 1 d . . . C27 C 0.35463(18) 0.55195(11) 0.37803(11) 0.0189(3) Uani 1 1 d . . . C28 C 0.3122(2) 0.45417(12) 0.29869(11) 0.0213(3) Uani 1 1 d . . . H28 H 0.350(2) 0.4498(15) 0.2369(13) 0.025(5) Uiso 1 1 d . . . C29 C 0.21962(19) 0.36186(12) 0.30765(11) 0.0188(3) Uani 1 1 d . . . H29 H 0.198(2) 0.2929(14) 0.2518(13) 0.021(4) Uiso 1 1 d . . . C30 C 0.4908(2) 0.73958(13) 0.44219(13) 0.0261(3) Uani 1 1 d . . . H30A H 0.554(2) 0.7903(14) 0.4179(12) 0.020(4) Uiso 1 1 d . . . H30B H 0.563(2) 0.7281(14) 0.5075(13) 0.023(4) Uiso 1 1 d . . . H30C H 0.387(3) 0.7742(15) 0.4554(14) 0.029(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0200(5) 0.0150(4) 0.0146(4) 0.0035(3) 0.0034(4) -0.0033(4) O2 0.0253(6) 0.0201(5) 0.0147(5) 0.0036(4) 0.0009(4) -0.0074(4) O3 0.0257(6) 0.0252(5) 0.0242(5) 0.0106(4) -0.0022(4) -0.0110(4) O4 0.0235(5) 0.0243(5) 0.0195(5) 0.0116(4) 0.0027(4) -0.0060(4) O5 0.0239(5) 0.0175(4) 0.0207(5) 0.0061(4) 0.0043(4) -0.0057(4) C1 0.0162(6) 0.0139(5) 0.0169(6) 0.0040(5) 0.0032(5) -0.0024(5) C2 0.0166(6) 0.0146(5) 0.0155(6) 0.0053(5) 0.0033(5) -0.0018(5) C3 0.0166(6) 0.0144(5) 0.0155(6) 0.0048(4) 0.0033(5) -0.0006(5) C4 0.0177(6) 0.0143(5) 0.0134(6) 0.0026(4) 0.0021(5) -0.0016(5) C5 0.0303(9) 0.0237(7) 0.0148(6) 0.0050(5) 0.0016(6) -0.0050(6) C6 0.0202(7) 0.0166(6) 0.0175(6) 0.0063(5) 0.0038(5) 0.0007(5) C7 0.0274(9) 0.0315(8) 0.0280(8) 0.0189(7) 0.0068(7) -0.0033(6) C8 0.0222(7) 0.0217(6) 0.0151(6) 0.0053(5) 0.0025(5) -0.0031(5) C9 0.0169(6) 0.0137(5) 0.0156(6) 0.0034(4) 0.0050(5) -0.0003(5) C10 0.0212(7) 0.0184(6) 0.0153(6) 0.0057(5) 0.0023(5) -0.0032(5) C11 0.0206(7) 0.0189(6) 0.0174(6) 0.0042(5) 0.0018(5) -0.0054(5) C12 0.0201(7) 0.0132(5) 0.0184(6) 0.0029(5) 0.0064(5) -0.0015(5) C13 0.0210(7) 0.0186(6) 0.0188(6) 0.0079(5) 0.0040(5) -0.0010(5) C14 0.0195(7) 0.0180(6) 0.0155(6) 0.0046(5) 0.0026(5) -0.0027(5) C15 0.0257(8) 0.0196(6) 0.0230(7) 0.0069(5) 0.0096(6) -0.0029(6) O6 0.0193(5) 0.0156(4) 0.0143(4) 0.0034(3) 0.0035(4) -0.0038(4) O7 0.0256(6) 0.0198(4) 0.0150(5) 0.0018(4) 0.0042(4) -0.0080(4) O8 0.0251(6) 0.0206(5) 0.0216(5) 0.0065(4) 0.0043(4) -0.0071(4) O9 0.0229(5) 0.0208(5) 0.0164(5) 0.0074(4) 0.0056(4) -0.0034(4) O10 0.0278(6) 0.0212(5) 0.0299(6) 0.0104(4) 0.0072(5) -0.0072(4) C16 0.0163(6) 0.0147(5) 0.0168(6) 0.0036(5) 0.0033(5) -0.0019(5) C17 0.0173(6) 0.0152(5) 0.0168(6) 0.0048(5) 0.0047(5) -0.0004(5) C18 0.0164(6) 0.0152(5) 0.0148(6) 0.0041(4) 0.0035(5) -0.0007(5) C19 0.0171(6) 0.0152(5) 0.0143(6) 0.0038(4) 0.0023(5) -0.0021(5) C20 0.0287(8) 0.0273(7) 0.0145(6) 0.0017(6) 0.0068(6) -0.0080(6) C21 0.0176(6) 0.0172(6) 0.0182(6) 0.0073(5) 0.0053(5) 0.0020(5) C22 0.0234(8) 0.0247(7) 0.0218(7) 0.0123(6) 0.0078(6) 0.0002(6) C23 0.0225(7) 0.0205(6) 0.0146(6) 0.0040(5) 0.0030(5) -0.0030(5) C24 0.0149(6) 0.0166(5) 0.0166(6) 0.0064(5) 0.0029(5) 0.0000(5) C25 0.0214(7) 0.0179(6) 0.0169(6) 0.0053(5) 0.0044(5) -0.0010(5) C26 0.0206(7) 0.0159(6) 0.0220(7) 0.0047(5) 0.0045(5) -0.0016(5) C27 0.0154(6) 0.0178(6) 0.0246(7) 0.0100(5) 0.0028(5) -0.0028(5) C28 0.0217(7) 0.0247(7) 0.0195(7) 0.0087(5) 0.0061(6) -0.0015(5) C29 0.0205(7) 0.0182(6) 0.0175(6) 0.0049(5) 0.0046(5) -0.0020(5) C30 0.0234(8) 0.0176(6) 0.0376(9) 0.0104(6) 0.0047(7) -0.0027(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 C1 1.3403(15) . ? O1 C4 1.4023(16) . ? O2 C1 1.3181(16) . ? O2 C5 1.4512(17) . ? O3 C6 1.2136(17) . ? O4 C6 1.3503(17) . ? O4 C7 1.4397(17) . ? O5 C12 1.3719(16) . ? O5 C15 1.4295(17) . ? C1 C2 1.3730(18) . ? C2 C6 1.4509(18) . ? C2 C3 1.4554(18) . ? C3 C4 1.3591(18) . ? C3 C8 1.4944(19) . ? C4 C9 1.4559(18) . ? C5 H5A 0.914(18) . ? C5 H5B 0.98(2) . ? C5 H5C 0.99(2) . ? C7 H7A 0.95(2) . ? C7 H7B 0.958(18) . ? C7 H7C 1.00(2) . ? C8 H8A 0.960(18) . ? C8 H8B 1.01(2) . ? C8 H8C 1.00(2) . ? C9 C14 1.3922(19) . ? C9 C10 1.4022(19) . ? C10 C11 1.3823(19) . ? C10 H10 0.976(18) . ? C11 C12 1.390(2) . ? C11 H11 0.972(19) . ? C12 C13 1.389(2) . ? C13 C14 1.3887(19) . ? C13 H13 0.967(16) . ? C14 H14 0.958(18) . ? C15 H15A 0.992(19) . ? C15 H15B 1.000(17) . ? C15 H15C 0.998(18) . ? O6 C16 1.3398(15) . ? O6 C19 1.4022(16) . ? O7 C16 1.3155(16) . ? O7 C20 1.4466(17) . ? O8 C21 1.2127(16) . ? O9 C21 1.3448(17) . ? O9 C22 1.4393(17) . ? O10 C27 1.3661(16) . ? O10 C30 1.4289(19) . ? C16 C17 1.3677(19) . ? C17 C21 1.4569(18) . ? C17 C18 1.4567(18) . ? C18 C19 1.3637(18) . ? C18 C23 1.4914(19) . ? C19 C24 1.4583(18) . ? C20 H20A 0.928(18) . ? C20 H20B 0.969(18) . ? C20 H20C 0.976(19) . ? C22 H22A 0.961(19) . ? C22 H22B 1.021(18) . ? C22 H22C 0.965(19) . ? C23 H23A 1.019(18) . ? C23 H23B 0.986(19) . ? C23 H23C 0.95(2) . ? C24 C25 1.3903(19) . ? C24 C29 1.4049(19) . ? C25 C26 1.3898(19) . ? C25 H25 0.972(17) . ? C26 C27 1.391(2) . ? C26 H26 0.970(17) . ? C27 C28 1.393(2) . ? C28 C29 1.3805(19) . ? C28 H28 0.975(18) . ? C29 H29 0.981(17) . ? C30 H30A 0.960(17) . ? C30 H30B 1.031(18) . ? C30 H30C 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 107.04(10) . . ? C1 O2 C5 116.71(11) . . ? C6 O4 C7 114.92(11) . . ? C12 O5 C15 116.49(11) . . ? O2 C1 O1 118.36(11) . . ? O2 C1 C2 130.14(12) . . ? O1 C1 C2 111.44(11) . . ? C1 C2 C6 124.13(12) . . ? C1 C2 C3 105.51(11) . . ? C6 C2 C3 130.36(12) . . ? C4 C3 C2 106.37(11) . . ? C4 C3 C8 126.53(12) . . ? C2 C3 C8 127.03(12) . . ? C3 C4 O1 109.65(11) . . ? C3 C4 C9 135.80(12) . . ? O1 C4 C9 114.53(11) . . ? O2 C5 H5A 105.5(11) . . ? O2 C5 H5B 109.4(11) . . ? H5A C5 H5B 110.8(15) . . ? O2 C5 H5C 109.8(12) . . ? H5A C5 H5C 110.3(16) . . ? H5B C5 H5C 110.9(16) . . ? O3 C6 O4 121.96(12) . . ? O3 C6 C2 125.47(13) . . ? O4 C6 C2 112.57(11) . . ? O4 C7 H7A 106.1(12) . . ? O4 C7 H7B 111.1(10) . . ? H7A C7 H7B 108.8(16) . . ? O4 C7 H7C 110.7(11) . . ? H7A C7 H7C 111.0(16) . . ? H7B C7 H7C 109.0(15) . . ? C3 C8 H8A 111.3(11) . . ? C3 C8 H8B 111.1(11) . . ? H8A C8 H8B 110.3(15) . . ? C3 C8 H8C 113.0(11) . . ? H8A C8 H8C 104.5(15) . . ? H8B C8 H8C 106.3(15) . . ? C14 C9 C10 117.87(12) . . ? C14 C9 C4 120.87(12) . . ? C10 C9 C4 121.25(12) . . ? C11 C10 C9 120.94(13) . . ? C11 C10 H10 119.5(11) . . ? C9 C10 H10 119.5(11) . . ? C10 C11 C12 120.28(13) . . ? C10 C11 H11 120.0(11) . . ? C12 C11 H11 119.7(11) . . ? O5 C12 C11 116.23(12) . . ? O5 C12 C13 124.06(12) . . ? C11 C12 C13 119.71(12) . . ? C14 C13 C12 119.61(13) . . ? C14 C13 H13 120.1(10) . . ? C12 C13 H13 120.3(9) . . ? C13 C14 C9 121.56(13) . . ? C13 C14 H14 119.6(11) . . ? C9 C14 H14 118.9(11) . . ? O5 C15 H15A 106.1(11) . . ? O5 C15 H15B 111.1(9) . . ? H15A C15 H15B 109.9(14) . . ? O5 C15 H15C 111.4(10) . . ? H15A C15 H15C 109.8(15) . . ? H15B C15 H15C 108.6(14) . . ? C16 O6 C19 107.06(10) . . ? C16 O7 C20 116.25(11) . . ? C21 O9 C22 115.47(11) . . ? C27 O10 C30 116.72(12) . . ? O7 C16 O6 118.27(11) . . ? O7 C16 C17 130.04(12) . . ? O6 C16 C17 111.65(11) . . ? C16 C17 C21 123.43(12) . . ? C16 C17 C18 105.54(11) . . ? C21 C17 C18 131.02(12) . . ? C19 C18 C17 106.25(11) . . ? C19 C18 C23 127.26(12) . . ? C17 C18 C23 126.47(12) . . ? C18 C19 O6 109.44(11) . . ? C18 C19 C24 136.17(12) . . ? O6 C19 C24 114.37(11) . . ? O7 C20 H20A 105.1(11) . . ? O7 C20 H20B 109.2(10) . . ? H20A C20 H20B 111.2(15) . . ? O7 C20 H20C 107.9(11) . . ? H20A C20 H20C 110.6(15) . . ? H20B C20 H20C 112.5(14) . . ? O8 C21 O9 122.90(12) . . ? O8 C21 C17 124.88(13) . . ? O9 C21 C17 112.20(11) . . ? O9 C22 H22A 105.1(11) . . ? O9 C22 H22B 109.4(10) . . ? H22A C22 H22B 112.5(15) . . ? O9 C22 H22C 110.0(11) . . ? H22A C22 H22C 111.9(15) . . ? H22B C22 H22C 107.9(15) . . ? C18 C23 H23A 112.9(10) . . ? C18 C23 H23B 111.0(11) . . ? H23A C23 H23B 105.0(15) . . ? C18 C23 H23C 113.1(11) . . ? H23A C23 H23C 107.9(15) . . ? H23B C23 H23C 106.4(16) . . ? C25 C24 C29 117.52(12) . . ? C25 C24 C19 121.76(12) . . ? C29 C24 C19 120.69(12) . . ? C26 C25 C24 121.85(13) . . ? C26 C25 H25 116.9(10) . . ? C24 C25 H25 121.2(10) . . ? C25 C26 C27 119.69(13) . . ? C25 C26 H26 118.5(10) . . ? C27 C26 H26 121.6(10) . . ? O10 C27 C26 124.72(13) . . ? O10 C27 C28 115.94(13) . . ? C26 C27 C28 119.33(12) . . ? C29 C28 C27 120.42(13) . . ? C29 C28 H28 119.5(10) . . ? C27 C28 H28 120.1(10) . . ? C28 C29 C24 121.15(13) . . ? C28 C29 H29 118.1(10) . . ? C24 C29 H29 120.7(10) . . ? O10 C30 H30A 105.4(10) . . ? O10 C30 H30B 113.2(10) . . ? H30A C30 H30B 110.1(14) . . ? O10 C30 H30C 110.8(11) . . ? H30A C30 H30C 107.3(15) . . ? H30B C30 H30C 109.7(15) . . ? 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 C1 O1 -8.36(19) . . . . ? C5 O2 C1 C2 174.68(15) . . . . ? C4 O1 C1 O2 -177.46(12) . . . . ? C4 O1 C1 C2 0.05(15) . . . . ? O2 C1 C2 C6 -3.6(2) . . . . ? O1 C1 C2 C6 179.29(13) . . . . ? O2 C1 C2 C3 177.20(14) . . . . ? O1 C1 C2 C3 0.07(16) . . . . ? C1 C2 C3 C4 -0.17(16) . . . . ? C6 C2 C3 C4 -179.32(14) . . . . ? C1 C2 C3 C8 176.78(14) . . . . ? C6 C2 C3 C8 -2.4(2) . . . . ? C2 C3 C4 O1 0.20(16) . . . . ? C8 C3 C4 O1 -176.76(13) . . . . ? C2 C3 C4 C9 178.17(16) . . . . ? C8 C3 C4 C9 1.2(3) . . . . ? C1 O1 C4 C3 -0.16(15) . . . . ? C1 O1 C4 C9 -178.60(12) . . . . ? C7 O4 C6 O3 0.1(2) . . . . ? C7 O4 C6 C2 180.00(13) . . . . ? C1 C2 C6 O3 -14.2(2) . . . . ? C3 C2 C6 O3 164.82(15) . . . . ? C1 C2 C6 O4 165.95(13) . . . . ? C3 C2 C6 O4 -15.0(2) . . . . ? C3 C4 C9 C14 -155.45(17) . . . . ? O1 C4 C9 C14 22.45(19) . . . . ? C3 C4 C9 C10 25.2(3) . . . . ? O1 C4 C9 C10 -156.91(13) . . . . ? C14 C9 C10 C11 1.8(2) . . . . ? C4 C9 C10 C11 -178.83(13) . . . . ? C9 C10 C11 C12 -0.8(2) . . . . ? C15 O5 C12 C11 167.97(13) . . . . ? C15 O5 C12 C13 -11.4(2) . . . . ? C10 C11 C12 O5 179.67(13) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? O5 C12 C13 C14 -179.08(13) . . . . ? C11 C12 C13 C14 1.5(2) . . . . ? C12 C13 C14 C9 -0.5(2) . . . . ? C10 C9 C14 C13 -1.1(2) . . . . ? C4 C9 C14 C13 179.47(13) . . . . ? C20 O7 C16 O6 -1.06(19) . . . . ? C20 O7 C16 C17 -178.65(16) . . . . ? C19 O6 C16 O7 -177.82(12) . . . . ? C19 O6 C16 C17 0.20(16) . . . . ? O7 C16 C17 C21 -5.2(3) . . . . ? O6 C16 C17 C21 177.07(12) . . . . ? O7 C16 C17 C18 176.07(14) . . . . ? O6 C16 C17 C18 -1.66(16) . . . . ? C16 C17 C18 C19 2.48(16) . . . . ? C21 C17 C18 C19 -176.11(15) . . . . ? C16 C17 C18 C23 -175.59(14) . . . . ? C21 C17 C18 C23 5.8(2) . . . . ? C17 C18 C19 O6 -2.43(15) . . . . ? C23 C18 C19 O6 175.62(13) . . . . ? C17 C18 C19 C24 176.35(16) . . . . ? C23 C18 C19 C24 -5.6(3) . . . . ? C16 O6 C19 C18 1.47(15) . . . . ? C16 O6 C19 C24 -177.60(12) . . . . ? C22 O9 C21 O8 -1.2(2) . . . . ? C22 O9 C21 C17 177.26(12) . . . . ? C16 C17 C21 O8 -3.1(2) . . . . ? C18 C17 C21 O8 175.31(14) . . . . ? C16 C17 C21 O9 178.49(13) . . . . ? C18 C17 C21 O9 -3.1(2) . . . . ? C18 C19 C24 C25 -17.4(3) . . . . ? O6 C19 C24 C25 161.37(13) . . . . ? C18 C19 C24 C29 164.40(16) . . . . ? O6 C19 C24 C29 -16.86(19) . . . . ? C29 C24 C25 C26 -2.1(2) . . . . ? C19 C24 C25 C26 179.64(14) . . . . ? C24 C25 C26 C27 1.4(2) . . . . ? C30 O10 C27 C26 -0.7(2) . . . . ? C30 O10 C27 C28 178.80(14) . . . . ? C25 C26 C27 O10 179.93(14) . . . . ? C25 C26 C27 C28 0.4(2) . . . . ? O10 C27 C28 C29 178.90(14) . . . . ? C26 C27 C28 C29 -1.6(2) . . . . ? C27 C28 C29 C24 0.9(2) . . . . ? C25 C24 C29 C28 0.9(2) . . . . ? C19 C24 C29 C28 179.23(14) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.533 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.070 # Attachment 'web_deposit_cif_file_2_WilliamW.Brennessel_1341257024.ritmc06.cif' data_ritmc06 _database_code_depnum_ccdc_archive 'CCDC 889656' #TrackingRef 'web_deposit_cif_file_2_WilliamW.Brennessel_1341257024.ritmc06.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ritmc06 _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 O5 Si' _chemical_formula_sum 'C21 H30 O5 Si' _chemical_formula_weight 390.54 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' 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' '-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 23.271(3) _cell_length_b 7.4790(11) _cell_length_c 25.546(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.779(2) _cell_angle_gamma 90.00 _cell_volume 4381.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3107 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 21.01 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; Crystals placed into the cold stream at lower temperatures tended to shatter, or they shattered during data collection. ; _diffrn_ambient_temperature 223(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 APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22446 _diffrn_reflns_av_R_equivalents 0.0883 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3874 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0600P)^2^+2.0113P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3874 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 Si1 Si 0.56420(3) 0.23993(11) 0.61842(4) 0.0498(3) Uani 1 1 d . . . O1 O 0.80800(8) 0.2079(3) 0.73788(8) 0.0497(5) Uani 1 1 d . . . O2 O 0.73157(11) 0.0747(4) 0.56567(9) 0.0836(8) Uani 1 1 d . . . O3 O 0.82615(10) 0.1353(3) 0.58111(9) 0.0726(7) Uani 1 1 d . . . O4 O 0.63321(8) 0.2377(3) 0.64456(8) 0.0540(6) Uani 1 1 d . . . O5 O 0.64043(11) 0.1845(4) 0.91155(10) 0.0827(8) Uani 1 1 d . . . C1 C 0.82374(13) 0.1956(4) 0.68924(13) 0.0510(8) Uani 1 1 d . . . C2 C 0.77645(12) 0.1481(4) 0.65294(12) 0.0480(7) Uani 1 1 d . . . C3 C 0.72817(12) 0.1315(4) 0.68099(12) 0.0459(7) Uani 1 1 d . . . C4 C 0.74934(12) 0.1697(4) 0.73232(12) 0.0459(7) Uani 1 1 d . . . C5 C 0.88566(13) 0.2361(5) 0.68803(14) 0.0655(9) Uani 1 1 d . . . H5A H 0.9000 0.3206 0.7160 0.098 Uiso 1 1 calc R . . H5B H 0.8893 0.2874 0.6539 0.098 Uiso 1 1 calc R . . H5C H 0.9083 0.1268 0.6934 0.098 Uiso 1 1 calc R . . C6 C 0.77441(15) 0.1150(4) 0.59655(13) 0.0561(8) Uani 1 1 d . . . C7 C 0.82827(17) 0.0984(6) 0.52608(14) 0.0836(12) Uani 1 1 d . . . H7A H 0.8684 0.1034 0.5203 0.125 Uiso 1 1 calc R . . H7B H 0.8053 0.1869 0.5039 0.125 Uiso 1 1 calc R . . H7C H 0.8125 -0.0198 0.5170 0.125 Uiso 1 1 calc R . . C8 C 0.66715(12) 0.0799(4) 0.65937(12) 0.0506(8) Uani 1 1 d . . . H8A H 0.6664 0.0027 0.6283 0.061 Uiso 1 1 calc R . . H8B H 0.6505 0.0132 0.6862 0.061 Uiso 1 1 calc R . . C9 C 0.55285(18) 0.1378(6) 0.55141(15) 0.0901(13) Uani 1 1 d . . . H9A H 0.5604 0.0104 0.5546 0.135 Uiso 1 1 calc R . . H9B H 0.5793 0.1920 0.5305 0.135 Uiso 1 1 calc R . . H9C H 0.5129 0.1576 0.5341 0.135 Uiso 1 1 calc R . . C10 C 0.52166(16) 0.1139(5) 0.66087(18) 0.0923(13) Uani 1 1 d . . . H10A H 0.5287 0.1635 0.6965 0.138 Uiso 1 1 calc R . . H10B H 0.5335 -0.0106 0.6622 0.138 Uiso 1 1 calc R . . H10C H 0.4805 0.1225 0.6463 0.138 Uiso 1 1 calc R . . C11 C 0.54467(13) 0.4822(4) 0.61511(12) 0.0525(8) Uani 1 1 d . . . C12 C 0.58441(15) 0.5819(5) 0.58290(15) 0.0799(11) Uani 1 1 d . . . H12A H 0.5744 0.7079 0.5813 0.120 Uiso 1 1 calc R . . H12B H 0.5793 0.5333 0.5472 0.120 Uiso 1 1 calc R . . H12C H 0.6247 0.5677 0.5998 0.120 Uiso 1 1 calc R . . C13 C 0.48144(14) 0.5074(5) 0.58787(15) 0.0738(10) Uani 1 1 d . . . H13A H 0.4720 0.6339 0.5862 0.111 Uiso 1 1 calc R . . H13B H 0.4557 0.4455 0.6080 0.111 Uiso 1 1 calc R . . H13C H 0.4765 0.4590 0.5522 0.111 Uiso 1 1 calc R . . C14 C 0.55252(17) 0.5584(5) 0.67107(14) 0.0848(12) Uani 1 1 d . . . H14A H 0.5421 0.6841 0.6694 0.127 Uiso 1 1 calc R . . H14B H 0.5929 0.5453 0.6880 0.127 Uiso 1 1 calc R . . H14C H 0.5276 0.4945 0.6915 0.127 Uiso 1 1 calc R . . C15 C 0.72344(12) 0.1749(4) 0.77989(12) 0.0467(7) Uani 1 1 d . . . C16 C 0.66683(13) 0.2389(4) 0.77811(13) 0.0551(8) Uani 1 1 d . . . H16A H 0.6461 0.2821 0.7458 0.066 Uiso 1 1 calc R . . C17 C 0.64087(14) 0.2403(5) 0.82183(14) 0.0621(9) Uani 1 1 d . . . H17A H 0.6026 0.2837 0.8195 0.075 Uiso 1 1 calc R . . C18 C 0.67051(15) 0.1784(4) 0.86941(14) 0.0582(9) Uani 1 1 d . . . C19 C 0.72694(15) 0.1177(4) 0.87327(13) 0.0636(9) Uani 1 1 d . . . H19A H 0.7477 0.0780 0.9060 0.076 Uiso 1 1 calc R . . C20 C 0.75283(14) 0.1160(4) 0.82815(13) 0.0574(8) Uani 1 1 d . . . H20A H 0.7912 0.0737 0.8306 0.069 Uiso 1 1 calc R . . C21 C 0.6670(2) 0.1061(6) 0.95963(15) 0.1020(15) Uani 1 1 d . . . H21A H 0.6405 0.1120 0.9851 0.153 Uiso 1 1 calc R . . H21B H 0.7026 0.1700 0.9734 0.153 Uiso 1 1 calc R . . H21C H 0.6761 -0.0179 0.9535 0.153 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 Si1 0.0388(5) 0.0448(5) 0.0626(6) -0.0023(4) -0.0002(4) 0.0016(4) O1 0.0385(11) 0.0522(13) 0.0563(13) 0.0008(10) 0.0022(9) 0.0042(9) O2 0.0674(16) 0.125(2) 0.0542(15) -0.0003(14) -0.0017(13) 0.0011(15) O3 0.0609(15) 0.0968(19) 0.0622(15) 0.0008(13) 0.0160(12) 0.0135(14) O4 0.0408(11) 0.0420(12) 0.0739(14) 0.0038(10) -0.0057(10) 0.0102(10) O5 0.0871(18) 0.090(2) 0.0744(18) 0.0069(14) 0.0246(15) 0.0056(14) C1 0.0451(18) 0.0496(19) 0.058(2) 0.0060(15) 0.0079(16) 0.0096(14) C2 0.0443(18) 0.0447(18) 0.0529(19) 0.0040(15) 0.0027(15) 0.0116(14) C3 0.0423(17) 0.0386(17) 0.0543(19) 0.0039(14) 0.0012(15) 0.0096(13) C4 0.0384(16) 0.0393(17) 0.058(2) 0.0042(14) 0.0028(15) 0.0070(13) C5 0.0437(18) 0.077(2) 0.075(2) 0.0063(19) 0.0096(16) 0.0026(17) C6 0.055(2) 0.053(2) 0.057(2) 0.0088(16) 0.0030(18) 0.0170(16) C7 0.087(3) 0.105(3) 0.063(2) 0.005(2) 0.023(2) 0.022(2) C8 0.0433(17) 0.0411(17) 0.064(2) -0.0010(15) -0.0022(14) 0.0073(14) C9 0.097(3) 0.079(3) 0.085(3) -0.025(2) -0.013(2) 0.011(2) C10 0.066(3) 0.076(3) 0.139(4) 0.030(3) 0.031(2) 0.008(2) C11 0.0465(18) 0.0495(19) 0.058(2) 0.0007(15) -0.0009(15) 0.0103(15) C12 0.069(2) 0.065(2) 0.101(3) 0.022(2) 0.001(2) -0.0022(19) C13 0.056(2) 0.071(2) 0.089(3) 0.011(2) -0.0020(18) 0.0211(19) C14 0.104(3) 0.061(2) 0.083(3) -0.018(2) -0.004(2) 0.027(2) C15 0.0468(18) 0.0378(17) 0.0540(19) -0.0029(14) 0.0046(15) 0.0003(13) C16 0.0494(18) 0.0516(19) 0.062(2) -0.0001(16) 0.0043(16) 0.0030(16) C17 0.0536(19) 0.066(2) 0.067(2) 0.0020(18) 0.0081(18) 0.0058(18) C18 0.062(2) 0.050(2) 0.067(2) -0.0003(16) 0.0218(19) -0.0031(17) C19 0.075(2) 0.056(2) 0.056(2) 0.0056(17) -0.0020(18) 0.0046(18) C20 0.055(2) 0.055(2) 0.060(2) -0.0003(17) 0.0024(17) 0.0061(16) C21 0.148(4) 0.089(3) 0.071(3) 0.021(2) 0.022(3) 0.020(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 Si1 O4 1.6312(19) . ? Si1 C10 1.846(4) . ? Si1 C9 1.852(4) . ? Si1 C11 1.866(3) . ? O1 C1 1.357(3) . ? O1 C4 1.378(3) . ? O2 C6 1.200(4) . ? O3 C6 1.338(4) . ? O3 C7 1.442(4) . ? O4 C8 1.435(3) . ? O5 C18 1.381(4) . ? O5 C21 1.406(4) . ? C1 C2 1.360(4) . ? C1 C5 1.478(4) . ? C2 C3 1.437(4) . ? C2 C6 1.454(4) . ? C3 C4 1.351(4) . ? C3 C8 1.485(4) . ? C4 C15 1.446(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 C14 1.521(4) . ? C11 C13 1.529(4) . ? C11 C12 1.532(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C15 C20 1.377(4) . ? C15 C16 1.395(4) . ? C16 C17 1.357(4) . ? C16 H16A 0.9400 . ? C17 C18 1.372(4) . ? C17 H17A 0.9400 . ? C18 C19 1.377(4) . ? C19 C20 1.388(4) . ? C19 H19A 0.9400 . ? C20 H20A 0.9400 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? 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 O4 Si1 C10 110.07(15) . . ? O4 Si1 C9 110.50(15) . . ? C10 Si1 C9 109.0(2) . . ? O4 Si1 C11 104.10(12) . . ? C10 Si1 C11 111.81(16) . . ? C9 Si1 C11 111.29(17) . . ? C1 O1 C4 108.0(2) . . ? C6 O3 C7 116.6(3) . . ? C8 O4 Si1 125.16(18) . . ? C18 O5 C21 117.5(3) . . ? O1 C1 C2 109.2(3) . . ? O1 C1 C5 114.9(3) . . ? C2 C1 C5 135.9(3) . . ? C1 C2 C3 107.0(3) . . ? C1 C2 C6 127.3(3) . . ? C3 C2 C6 125.6(3) . . ? C4 C3 C2 106.2(3) . . ? C4 C3 C8 125.7(3) . . ? C2 C3 C8 128.0(3) . . ? C3 C4 O1 109.6(3) . . ? C3 C4 C15 133.3(3) . . ? O1 C4 C15 117.1(3) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 O3 121.6(3) . . ? O2 C6 C2 125.3(3) . . ? O3 C6 C2 113.1(3) . . ? O3 C7 H7A 109.5 . . ? O3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 C3 109.5(2) . . ? O4 C8 H8A 109.8 . . ? C3 C8 H8A 109.8 . . ? O4 C8 H8B 109.8 . . ? C3 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? Si1 C9 H9A 109.5 . . ? Si1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Si1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C14 C11 C13 109.5(3) . . ? C14 C11 C12 109.6(3) . . ? C13 C11 C12 108.5(3) . . ? C14 C11 Si1 109.4(2) . . ? C13 C11 Si1 110.4(2) . . ? C12 C11 Si1 109.4(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.5(3) . . ? C20 C15 C4 122.0(3) . . ? C16 C15 C4 120.5(3) . . ? C17 C16 C15 121.7(3) . . ? C17 C16 H16A 119.1 . . ? C15 C16 H16A 119.1 . . ? C16 C17 C18 120.0(3) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C19 120.3(3) . . ? C17 C18 O5 115.8(3) . . ? C19 C18 O5 124.0(3) . . ? C18 C19 C20 119.1(3) . . ? C18 C19 H19A 120.4 . . ? C20 C19 H19A 120.4 . . ? C15 C20 C19 121.4(3) . . ? C15 C20 H20A 119.3 . . ? C19 C20 H20A 119.3 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? 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 C10 Si1 O4 C8 54.5(3) . . . . ? C9 Si1 O4 C8 -66.0(3) . . . . ? C11 Si1 O4 C8 174.4(2) . . . . ? C4 O1 C1 C2 -0.8(3) . . . . ? C4 O1 C1 C5 178.9(2) . . . . ? O1 C1 C2 C3 0.5(3) . . . . ? C5 C1 C2 C3 -179.1(3) . . . . ? O1 C1 C2 C6 -178.0(3) . . . . ? C5 C1 C2 C6 2.4(6) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C6 C2 C3 C4 178.5(3) . . . . ? C1 C2 C3 C8 -179.1(3) . . . . ? C6 C2 C3 C8 -0.5(5) . . . . ? C2 C3 C4 O1 -0.4(3) . . . . ? C8 C3 C4 O1 178.6(2) . . . . ? C2 C3 C4 C15 -179.3(3) . . . . ? C8 C3 C4 C15 -0.3(5) . . . . ? C1 O1 C4 C3 0.7(3) . . . . ? C1 O1 C4 C15 179.8(2) . . . . ? C7 O3 C6 O2 -2.8(5) . . . . ? C7 O3 C6 C2 177.8(3) . . . . ? C1 C2 C6 O2 -179.3(3) . . . . ? C3 C2 C6 O2 2.5(5) . . . . ? C1 C2 C6 O3 0.1(5) . . . . ? C3 C2 C6 O3 -178.1(3) . . . . ? Si1 O4 C8 C3 179.16(19) . . . . ? C4 C3 C8 O4 88.6(3) . . . . ? C2 C3 C8 O4 -92.6(3) . . . . ? O4 Si1 C11 C14 -63.0(3) . . . . ? C10 Si1 C11 C14 55.7(3) . . . . ? C9 Si1 C11 C14 177.9(3) . . . . ? O4 Si1 C11 C13 176.4(2) . . . . ? C10 Si1 C11 C13 -64.9(3) . . . . ? C9 Si1 C11 C13 57.3(3) . . . . ? O4 Si1 C11 C12 57.0(2) . . . . ? C10 Si1 C11 C12 175.8(2) . . . . ? C9 Si1 C11 C12 -62.0(3) . . . . ? C3 C4 C15 C20 141.4(3) . . . . ? O1 C4 C15 C20 -37.5(4) . . . . ? C3 C4 C15 C16 -37.9(5) . . . . ? O1 C4 C15 C16 143.2(3) . . . . ? C20 C15 C16 C17 -1.3(5) . . . . ? C4 C15 C16 C17 178.1(3) . . . . ? C15 C16 C17 C18 0.3(5) . . . . ? C16 C17 C18 C19 1.2(5) . . . . ? C16 C17 C18 O5 -179.7(3) . . . . ? C21 O5 C18 C17 173.8(3) . . . . ? C21 O5 C18 C19 -7.1(5) . . . . ? C17 C18 C19 C20 -1.6(5) . . . . ? O5 C18 C19 C20 179.4(3) . . . . ? C16 C15 C20 C19 0.9(5) . . . . ? C4 C15 C20 C19 -178.5(3) . . . . ? C18 C19 C20 C15 0.5(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.231 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.045 # Attachment 'web_deposit_cif_file_3_WilliamW.Brennessel_1341257024.ritmc08.cif' data_ritmc08 _database_code_depnum_ccdc_archive 'CCDC 889657' #TrackingRef 'web_deposit_cif_file_3_WilliamW.Brennessel_1341257024.ritmc08.cif' _vrf_PLAT094_ritmc08 ; PROBLEM: _C Ratio of Maximum / Minimum Residual Density .... 2.45 RESPONSE: The highest residual peaks of electron density are found in bonds, which are not modeled by SHELXL-97 (Sheldrick, 2008). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ritmc08 _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 O3' _chemical_formula_sum 'C19 H18 O3' _chemical_formula_weight 294.33 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9801(5) _cell_length_b 9.5704(6) _cell_length_c 11.5449(7) _cell_angle_alpha 105.321(1) _cell_angle_beta 108.834(1) _cell_angle_gamma 101.854(1) _cell_volume 762.94(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 3891 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 37.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details 'SADABS (Shedrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20351 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _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 2.00 _diffrn_reflns_theta_max 36.32 _reflns_number_total 7280 _reflns_number_gt 5426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0807P)^2^+0.0518P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7280 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 -0.24331(10) 0.67878(9) 0.25156(7) 0.02751(15) Uani 1 1 d . . . O2 O -0.19010(9) 0.71414(8) 0.46193(6) 0.02092(13) Uani 1 1 d . . . O3 O 0.25551(9) 0.63281(7) 0.10929(6) 0.01927(12) Uani 1 1 d . . . C1 C 0.06977(11) 0.73049(9) 0.40306(8) 0.01628(14) Uani 1 1 d . . . C2 C 0.12952(11) 0.65018(9) 0.29834(8) 0.01698(14) Uani 1 1 d . . . C3 C 0.15626(12) 0.79443(10) 0.32048(8) 0.01880(15) Uani 1 1 d . . . C4 C 0.22052(17) 0.93836(12) 0.30096(11) 0.0291(2) Uani 1 1 d . . . H4A H 0.229(2) 0.927(2) 0.2187(17) 0.049(5) Uiso 1 1 d . . . H4B H 0.132(2) 0.997(2) 0.3022(17) 0.050(5) Uiso 1 1 d . . . H4C H 0.348(3) 0.999(2) 0.3712(18) 0.054(5) Uiso 1 1 d . . . C5 C -0.13621(11) 0.70456(9) 0.36186(8) 0.01775(14) Uani 1 1 d . . . C6 C -0.38716(13) 0.68944(13) 0.42805(11) 0.02691(19) Uani 1 1 d . . . H6A H -0.4239(19) 0.7676(16) 0.3925(13) 0.027(3) Uiso 1 1 d . . . H6B H -0.400(2) 0.7040(17) 0.5111(15) 0.037(4) Uiso 1 1 d . . . H6C H -0.459(2) 0.5867(18) 0.3661(15) 0.039(4) Uiso 1 1 d . . . C7 C 0.18812(11) 0.77618(9) 0.54624(8) 0.01643(14) Uani 1 1 d . . . C8 C 0.21320(13) 0.91932(10) 0.63288(9) 0.02141(16) Uani 1 1 d . . . H8 H 0.147(2) 0.9862(16) 0.5987(13) 0.028(3) Uiso 1 1 d . . . C9 C 0.33145(14) 0.96937(11) 0.76418(9) 0.02542(18) Uani 1 1 d . . . H9 H 0.349(2) 1.0715(17) 0.8234(14) 0.034(4) Uiso 1 1 d . . . C10 C 0.42728(13) 0.87629(12) 0.81082(9) 0.02538(18) Uani 1 1 d . . . H10 H 0.513(2) 0.9100(17) 0.9004(15) 0.037(4) Uiso 1 1 d . . . C11 C 0.40276(13) 0.73342(12) 0.72631(9) 0.02507(18) Uani 1 1 d . . . H11 H 0.472(2) 0.6693(17) 0.7630(15) 0.038(4) Uiso 1 1 d . . . C12 C 0.28354(12) 0.68373(10) 0.59459(8) 0.02052(15) Uani 1 1 d . . . H12 H 0.267(2) 0.5839(16) 0.5347(14) 0.031(3) Uiso 1 1 d . . . C13 C 0.13184(11) 0.50419(9) 0.22383(8) 0.01626(14) Uani 1 1 d . . . C14 C 0.06623(12) 0.37052(10) 0.24511(9) 0.01995(15) Uani 1 1 d . . . H14 H 0.0227(19) 0.3730(15) 0.3114(13) 0.028(3) Uiso 1 1 d . . . C15 C 0.06207(13) 0.23081(10) 0.16674(10) 0.02298(17) Uani 1 1 d . . . H15 H 0.013(2) 0.1410(16) 0.1871(14) 0.032(3) Uiso 1 1 d . . . C16 C 0.12436(13) 0.22495(10) 0.06668(9) 0.02269(16) Uani 1 1 d . . . H16 H 0.121(2) 0.1259(18) 0.0097(15) 0.038(4) Uiso 1 1 d . . . C17 C 0.19199(12) 0.35699(10) 0.04384(9) 0.01949(15) Uani 1 1 d . . . H17 H 0.2295(19) 0.3494(16) -0.0287(13) 0.030(3) Uiso 1 1 d . . . C18 C 0.19610(10) 0.49696(9) 0.12258(8) 0.01565(13) Uani 1 1 d . . . C19 C 0.33288(12) 0.63473(11) 0.01377(9) 0.02102(16) Uani 1 1 d . . . H19A H 0.453(2) 0.6127(15) 0.0382(13) 0.029(3) Uiso 1 1 d . . . H19B H 0.3527(19) 0.7380(16) 0.0101(13) 0.028(3) Uiso 1 1 d . . . H19C H 0.2525(19) 0.5614(15) -0.0711(13) 0.024(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0211(3) 0.0415(4) 0.0162(3) 0.0054(3) 0.0043(2) 0.0139(3) O2 0.0152(3) 0.0286(3) 0.0176(3) 0.0049(2) 0.0078(2) 0.0064(2) O3 0.0225(3) 0.0194(3) 0.0193(3) 0.0072(2) 0.0118(2) 0.0075(2) C1 0.0165(3) 0.0187(3) 0.0143(3) 0.0045(3) 0.0070(3) 0.0074(3) C2 0.0169(3) 0.0205(3) 0.0152(3) 0.0058(3) 0.0081(3) 0.0077(3) C3 0.0208(3) 0.0217(3) 0.0168(3) 0.0076(3) 0.0097(3) 0.0082(3) C4 0.0406(6) 0.0237(4) 0.0323(5) 0.0140(4) 0.0218(5) 0.0121(4) C5 0.0177(3) 0.0194(3) 0.0155(3) 0.0034(3) 0.0066(3) 0.0084(3) C6 0.0159(4) 0.0323(5) 0.0287(5) 0.0036(4) 0.0105(3) 0.0068(3) C7 0.0144(3) 0.0196(3) 0.0148(3) 0.0052(3) 0.0064(3) 0.0049(2) C8 0.0207(4) 0.0213(4) 0.0187(4) 0.0037(3) 0.0063(3) 0.0069(3) C9 0.0236(4) 0.0250(4) 0.0188(4) 0.0001(3) 0.0063(3) 0.0038(3) C10 0.0213(4) 0.0319(4) 0.0153(4) 0.0053(3) 0.0035(3) 0.0033(3) C11 0.0233(4) 0.0308(4) 0.0193(4) 0.0101(3) 0.0049(3) 0.0094(3) C12 0.0204(4) 0.0227(4) 0.0172(3) 0.0059(3) 0.0062(3) 0.0079(3) C13 0.0149(3) 0.0189(3) 0.0152(3) 0.0052(3) 0.0064(3) 0.0065(2) C14 0.0205(3) 0.0223(4) 0.0199(4) 0.0093(3) 0.0094(3) 0.0080(3) C15 0.0241(4) 0.0199(4) 0.0260(4) 0.0091(3) 0.0102(3) 0.0077(3) C16 0.0236(4) 0.0195(4) 0.0238(4) 0.0049(3) 0.0094(3) 0.0086(3) C17 0.0188(3) 0.0208(3) 0.0179(3) 0.0037(3) 0.0077(3) 0.0078(3) C18 0.0133(3) 0.0188(3) 0.0145(3) 0.0052(3) 0.0053(3) 0.0059(2) C19 0.0200(4) 0.0262(4) 0.0168(3) 0.0073(3) 0.0093(3) 0.0046(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 O1 C5 1.2073(10) . ? O2 C5 1.3450(10) . ? O2 C6 1.4433(11) . ? O3 C18 1.3557(10) . ? O3 C19 1.4294(10) . ? C1 C5 1.5016(11) . ? C1 C7 1.5020(11) . ? C1 C2 1.5203(11) . ? C1 C3 1.5229(11) . ? C2 C3 1.2939(12) . ? C2 C13 1.4416(11) . ? C3 C4 1.4696(13) . ? C4 H4A 0.953(17) . ? C4 H4B 0.991(18) . ? C4 H4C 1.003(19) . ? C6 H6A 0.995(14) . ? C6 H6B 0.973(15) . ? C6 H6C 0.969(16) . ? C7 C12 1.3920(12) . ? C7 C8 1.3969(12) . ? C8 C9 1.3874(13) . ? C8 H8 0.991(14) . ? C9 C10 1.3913(15) . ? C9 H9 0.986(15) . ? C10 C11 1.3862(15) . ? C10 H10 0.957(15) . ? C11 C12 1.3934(13) . ? C11 H11 0.995(16) . ? C12 H12 0.974(14) . ? C13 C14 1.3946(11) . ? C13 C18 1.4118(10) . ? C14 C15 1.3895(13) . ? C14 H14 0.934(13) . ? C15 C16 1.3903(13) . ? C15 H15 0.989(14) . ? C16 C17 1.3947(12) . ? C16 H16 0.990(16) . ? C17 C18 1.3932(12) . ? C17 H17 0.967(13) . ? C19 H19A 0.991(14) . ? C19 H19B 0.983(14) . ? C19 H19C 0.954(13) . ? 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 C6 115.16(7) . . ? C18 O3 C19 117.61(7) . . ? C5 C1 C7 118.20(6) . . ? C5 C1 C2 115.91(7) . . ? C7 C1 C2 121.35(7) . . ? C5 C1 C3 115.29(7) . . ? C7 C1 C3 117.94(7) . . ? C2 C1 C3 50.32(5) . . ? C3 C2 C13 150.47(8) . . ? C3 C2 C1 64.94(6) . . ? C13 C2 C1 144.36(7) . . ? C2 C3 C4 154.08(8) . . ? C2 C3 C1 64.73(6) . . ? C4 C3 C1 141.17(8) . . ? C3 C4 H4A 114.8(10) . . ? C3 C4 H4B 111.3(10) . . ? H4A C4 H4B 103.8(14) . . ? C3 C4 H4C 108.8(10) . . ? H4A C4 H4C 107.3(15) . . ? H4B C4 H4C 110.7(15) . . ? O1 C5 O2 122.97(8) . . ? O1 C5 C1 124.37(7) . . ? O2 C5 C1 112.66(7) . . ? O2 C6 H6A 109.5(8) . . ? O2 C6 H6B 104.0(9) . . ? H6A C6 H6B 110.1(11) . . ? O2 C6 H6C 110.4(9) . . ? H6A C6 H6C 111.5(12) . . ? H6B C6 H6C 111.0(13) . . ? C12 C7 C8 118.55(8) . . ? C12 C7 C1 121.87(7) . . ? C8 C7 C1 119.46(7) . . ? C9 C8 C7 121.00(8) . . ? C9 C8 H8 120.1(8) . . ? C7 C8 H8 118.9(8) . . ? C8 C9 C10 119.79(9) . . ? C8 C9 H9 119.7(9) . . ? C10 C9 H9 120.5(9) . . ? C11 C10 C9 119.91(9) . . ? C11 C10 H10 119.0(9) . . ? C9 C10 H10 121.1(9) . . ? C10 C11 C12 120.01(9) . . ? C10 C11 H11 117.9(9) . . ? C12 C11 H11 122.1(9) . . ? C7 C12 C11 120.73(8) . . ? C7 C12 H12 119.0(8) . . ? C11 C12 H12 120.3(8) . . ? C14 C13 C18 119.48(7) . . ? C14 C13 C2 122.28(7) . . ? C18 C13 C2 118.19(7) . . ? C15 C14 C13 120.51(8) . . ? C15 C14 H14 118.8(8) . . ? C13 C14 H14 120.7(8) . . ? C14 C15 C16 119.50(8) . . ? C14 C15 H15 115.9(8) . . ? C16 C15 H15 124.6(8) . . ? C15 C16 C17 121.20(8) . . ? C15 C16 H16 120.1(9) . . ? C17 C16 H16 118.7(9) . . ? C18 C17 C16 119.20(8) . . ? C18 C17 H17 121.1(8) . . ? C16 C17 H17 119.6(8) . . ? O3 C18 C17 124.99(7) . . ? O3 C18 C13 114.88(7) . . ? C17 C18 C13 120.12(7) . . ? O3 C19 H19A 111.6(8) . . ? O3 C19 H19B 106.1(8) . . ? H19A C19 H19B 110.0(11) . . ? O3 C19 H19C 112.8(8) . . ? H19A C19 H19C 106.8(11) . . ? H19B C19 H19C 109.4(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 C5 C1 C2 C3 102.36(8) . . . . ? C7 C1 C2 C3 -101.98(9) . . . . ? C5 C1 C2 C13 -72.69(14) . . . . ? C7 C1 C2 C13 82.98(14) . . . . ? C3 C1 C2 C13 -175.05(15) . . . . ? C13 C2 C3 C4 -7.9(3) . . . . ? C1 C2 C3 C4 178.0(2) . . . . ? C13 C2 C3 C1 174.14(17) . . . . ? C5 C1 C3 C2 -103.65(8) . . . . ? C7 C1 C3 C2 108.98(8) . . . . ? C5 C1 C3 C4 77.76(15) . . . . ? C7 C1 C3 C4 -69.61(15) . . . . ? C2 C1 C3 C4 -178.60(15) . . . . ? C6 O2 C5 O1 0.73(12) . . . . ? C6 O2 C5 C1 -179.71(7) . . . . ? C7 C1 C5 O1 174.23(8) . . . . ? C2 C1 C5 O1 -29.31(12) . . . . ? C3 C1 C5 O1 26.95(12) . . . . ? C7 C1 C5 O2 -5.32(10) . . . . ? C2 C1 C5 O2 151.15(7) . . . . ? C3 C1 C5 O2 -152.60(7) . . . . ? C5 C1 C7 C12 116.47(9) . . . . ? C2 C1 C7 C12 -38.66(11) . . . . ? C3 C1 C7 C12 -97.12(9) . . . . ? C5 C1 C7 C8 -67.54(10) . . . . ? C2 C1 C7 C8 137.33(8) . . . . ? C3 C1 C7 C8 78.87(10) . . . . ? C12 C7 C8 C9 0.45(13) . . . . ? C1 C7 C8 C9 -175.67(8) . . . . ? C7 C8 C9 C10 0.16(14) . . . . ? C8 C9 C10 C11 -0.68(14) . . . . ? C9 C10 C11 C12 0.56(14) . . . . ? C8 C7 C12 C11 -0.57(12) . . . . ? C1 C7 C12 C11 175.46(8) . . . . ? C10 C11 C12 C7 0.06(14) . . . . ? C3 C2 C13 C14 -174.76(14) . . . . ? C1 C2 C13 C14 -3.89(17) . . . . ? C3 C2 C13 C18 2.6(2) . . . . ? C1 C2 C13 C18 173.49(10) . . . . ? C18 C13 C14 C15 -0.64(13) . . . . ? C2 C13 C14 C15 176.71(8) . . . . ? C13 C14 C15 C16 0.15(14) . . . . ? C14 C15 C16 C17 0.34(14) . . . . ? C15 C16 C17 C18 -0.32(13) . . . . ? C19 O3 C18 C17 -4.94(12) . . . . ? C19 O3 C18 C13 176.28(7) . . . . ? C16 C17 C18 O3 -178.91(8) . . . . ? C16 C17 C18 C13 -0.19(12) . . . . ? C14 C13 C18 O3 179.50(7) . . . . ? C2 C13 C18 O3 2.05(11) . . . . ? C14 C13 C18 C17 0.66(12) . . . . ? C2 C13 C18 C17 -176.79(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.549 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.059 # Attachment 'web_deposit_cif_file_4_WilliamW.Brennessel_1341257024.ritmc09.cif' data_ritmc09 _database_code_depnum_ccdc_archive 'CCDC 889658' #TrackingRef 'web_deposit_cif_file_4_WilliamW.Brennessel_1341257024.ritmc09.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ritmc09 _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 O6' _chemical_formula_sum 'C17 H18 O6' _chemical_formula_weight 318.31 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3285(5) _cell_length_b 9.7137(6) _cell_length_c 10.2280(6) _cell_angle_alpha 102.466(1) _cell_angle_beta 109.023(1) _cell_angle_gamma 97.827(1) _cell_volume 744.45(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 4082 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 37.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17284 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 34.97 _reflns_number_total 6476 _reflns_number_gt 4140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0691P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6476 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.22985(10) 0.44157(9) 0.12641(8) 0.01627(16) Uani 1 1 d . . . O2 O 0.52708(13) 0.80510(11) 0.01623(11) 0.0324(2) Uani 1 1 d . . . O3 O 0.63338(11) 0.80165(10) 0.24657(10) 0.02440(19) Uani 1 1 d . . . O4 O 0.10975(11) 0.62354(9) -0.23942(9) 0.01921(17) Uani 1 1 d . . . O5 O 0.17119(11) 0.62447(10) -0.43737(9) 0.02185(18) Uani 1 1 d . . . O6 O -0.37776(11) -0.06351(9) -0.34793(9) 0.02194(18) Uani 1 1 d . . . C1 C 0.36520(14) 0.55976(12) 0.19064(12) 0.0163(2) Uani 1 1 d . . . C2 C 0.39202(14) 0.61890(12) 0.08793(12) 0.0163(2) Uani 1 1 d . . . C3 C 0.26478(14) 0.53044(12) -0.04953(12) 0.0160(2) Uani 1 1 d . . . C4 C 0.16899(14) 0.42431(12) -0.02038(12) 0.0155(2) Uani 1 1 d . . . C5 C 0.44671(16) 0.59146(14) 0.34931(13) 0.0193(2) Uani 1 1 d . . . H5A H 0.510(2) 0.6897(19) 0.3911(19) 0.034(4) Uiso 1 1 d . . . H5B H 0.357(2) 0.5736(17) 0.3875(18) 0.028(4) Uiso 1 1 d . . . H5C H 0.528(2) 0.5284(17) 0.3769(17) 0.029(4) Uiso 1 1 d . . . C6 C 0.52077(15) 0.74925(13) 0.10945(13) 0.0187(2) Uani 1 1 d . . . C7 C 0.75695(17) 0.93463(14) 0.27661(17) 0.0266(3) Uani 1 1 d . . . H7B H 0.837(2) 0.9167(19) 0.222(2) 0.040(5) Uiso 1 1 d . . . H7C H 0.820(3) 0.965(2) 0.381(3) 0.065(7) Uiso 1 1 d . . . H7A H 0.693(3) 1.007(2) 0.250(2) 0.052(6) Uiso 1 1 d . . . C8 C 0.24979(15) 0.54842(13) -0.19320(12) 0.0174(2) Uani 1 1 d . . . H8A H 0.2223(18) 0.4541(15) -0.2657(16) 0.017(3) Uiso 1 1 d . . . H8B H 0.3615(18) 0.6063(15) -0.1882(15) 0.016(3) Uiso 1 1 d . . . C9 C 0.08597(14) 0.65531(12) -0.36429(12) 0.0178(2) Uani 1 1 d . . . C10 C -0.06046(17) 0.73162(15) -0.40092(15) 0.0241(2) Uani 1 1 d . . . H10B H -0.076(3) 0.758(2) -0.492(2) 0.050(5) Uiso 1 1 d . . . H10C H -0.043(2) 0.815(2) -0.321(2) 0.040(5) Uiso 1 1 d . . . H10A H -0.168(2) 0.667(2) -0.416(2) 0.044(5) Uiso 1 1 d . . . C11 C 0.02422(14) 0.30009(12) -0.10478(11) 0.01513(19) Uani 1 1 d . . . C12 C -0.07051(15) 0.27769(13) -0.25195(12) 0.0166(2) Uani 1 1 d . . . H12 H -0.0478(19) 0.3494(16) -0.2978(16) 0.021(4) Uiso 1 1 d . . . C13 C -0.20255(15) 0.15554(13) -0.32968(13) 0.0181(2) Uani 1 1 d . . . H13 H -0.271(2) 0.1426(17) -0.4328(17) 0.026(4) Uiso 1 1 d . . . C14 C -0.24603(14) 0.05350(12) -0.26264(12) 0.0174(2) Uani 1 1 d . . . C15 C -0.15742(15) 0.07625(13) -0.11555(13) 0.0185(2) Uani 1 1 d . . . H15 H -0.1907(19) 0.0081(17) -0.0692(17) 0.024(4) Uiso 1 1 d . . . C16 C -0.02378(15) 0.19803(13) -0.03903(12) 0.0176(2) Uani 1 1 d . . . H16 H 0.038(2) 0.2127(18) 0.0663(18) 0.030(4) Uiso 1 1 d . . . C17 C -0.42639(17) -0.16683(14) -0.27971(14) 0.0224(2) Uani 1 1 d . . . H17A H -0.332(2) -0.2169(16) -0.2459(17) 0.025(4) Uiso 1 1 d . . . H17B H -0.464(2) -0.1244(17) -0.2041(18) 0.028(4) Uiso 1 1 d . . . H17C H -0.526(2) -0.2357(17) -0.3504(17) 0.026(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0170(3) 0.0184(4) 0.0126(4) 0.0051(3) 0.0043(3) 0.0028(3) O2 0.0328(5) 0.0323(5) 0.0272(5) 0.0145(4) 0.0056(4) -0.0053(4) O3 0.0231(4) 0.0234(4) 0.0209(4) 0.0035(3) 0.0058(3) -0.0035(3) O4 0.0209(4) 0.0250(4) 0.0163(4) 0.0101(3) 0.0080(3) 0.0096(3) O5 0.0197(4) 0.0291(5) 0.0171(4) 0.0086(3) 0.0070(3) 0.0021(3) O6 0.0230(4) 0.0199(4) 0.0172(4) 0.0058(3) 0.0019(3) -0.0012(3) C1 0.0155(4) 0.0174(5) 0.0154(5) 0.0045(4) 0.0049(4) 0.0035(4) C2 0.0151(4) 0.0184(5) 0.0160(5) 0.0057(4) 0.0060(4) 0.0042(4) C3 0.0168(5) 0.0177(5) 0.0150(5) 0.0057(4) 0.0064(4) 0.0050(4) C4 0.0171(5) 0.0171(5) 0.0125(4) 0.0047(4) 0.0049(4) 0.0048(4) C5 0.0189(5) 0.0236(6) 0.0145(5) 0.0061(4) 0.0051(4) 0.0037(4) C6 0.0170(5) 0.0198(5) 0.0200(5) 0.0059(4) 0.0073(4) 0.0044(4) C7 0.0221(6) 0.0192(6) 0.0334(7) 0.0014(5) 0.0095(5) -0.0006(5) C8 0.0182(5) 0.0211(5) 0.0156(5) 0.0076(4) 0.0075(4) 0.0063(4) C9 0.0174(5) 0.0169(5) 0.0151(5) 0.0050(4) 0.0024(4) -0.0010(4) C10 0.0243(6) 0.0243(6) 0.0222(6) 0.0091(5) 0.0043(5) 0.0071(5) C11 0.0167(4) 0.0165(5) 0.0132(5) 0.0053(4) 0.0056(4) 0.0048(4) C12 0.0186(5) 0.0179(5) 0.0147(5) 0.0069(4) 0.0060(4) 0.0048(4) C13 0.0197(5) 0.0196(5) 0.0146(5) 0.0057(4) 0.0047(4) 0.0050(4) C14 0.0176(5) 0.0168(5) 0.0162(5) 0.0043(4) 0.0044(4) 0.0037(4) C15 0.0204(5) 0.0182(5) 0.0169(5) 0.0072(4) 0.0059(4) 0.0033(4) C16 0.0192(5) 0.0193(5) 0.0140(5) 0.0062(4) 0.0048(4) 0.0039(4) C17 0.0209(5) 0.0214(6) 0.0227(6) 0.0076(5) 0.0060(5) 0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3636(14) . ? O1 C4 1.3825(13) . ? O2 C6 1.2060(15) . ? O3 C6 1.3453(15) . ? O3 C7 1.4430(16) . ? O4 C9 1.3370(14) . ? O4 C8 1.4620(13) . ? O5 C9 1.2080(14) . ? O6 C14 1.3657(14) . ? O6 C17 1.4261(15) . ? C1 C2 1.3645(16) . ? C1 C5 1.4828(16) . ? C2 C3 1.4482(16) . ? C2 C6 1.4688(17) . ? C3 C4 1.3608(16) . ? C3 C8 1.4842(16) . ? C4 C11 1.4596(16) . ? C5 H5A 0.955(18) . ? C5 H5B 0.961(16) . ? C5 H5C 0.986(16) . ? C7 H7B 1.004(18) . ? C7 H7C 0.98(2) . ? C7 H7A 0.97(2) . ? C8 H8A 0.990(14) . ? C8 H8B 0.999(14) . ? C9 C10 1.4985(17) . ? C10 H10B 1.00(2) . ? C10 H10C 0.971(18) . ? C10 H10A 0.969(19) . ? C11 C16 1.3965(16) . ? C11 C12 1.4047(15) . ? C12 C13 1.3844(17) . ? C12 H12 0.950(15) . ? C13 C14 1.3933(16) . ? C13 H13 0.992(16) . ? C14 C15 1.3947(16) . ? C15 C16 1.3872(16) . ? C15 H15 0.955(16) . ? C16 H16 0.999(17) . ? C17 H17A 0.985(15) . ? C17 H17B 0.963(16) . ? C17 H17C 0.954(16) . ? 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 O1 C4 108.21(9) . . ? C6 O3 C7 115.25(11) . . ? C9 O4 C8 115.62(9) . . ? C14 O6 C17 116.87(9) . . ? O1 C1 C2 109.31(10) . . ? O1 C1 C5 114.67(10) . . ? C2 C1 C5 136.02(11) . . ? C1 C2 C3 106.90(10) . . ? C1 C2 C6 127.65(11) . . ? C3 C2 C6 125.43(10) . . ? C4 C3 C2 106.20(10) . . ? C4 C3 C8 127.35(10) . . ? C2 C3 C8 126.37(10) . . ? C3 C4 O1 109.38(10) . . ? C3 C4 C11 135.90(10) . . ? O1 C4 C11 114.71(9) . . ? C1 C5 H5A 110.7(11) . . ? C1 C5 H5B 109.0(10) . . ? H5A C5 H5B 109.8(14) . . ? C1 C5 H5C 111.3(9) . . ? H5A C5 H5C 108.3(14) . . ? H5B C5 H5C 107.7(13) . . ? O2 C6 O3 122.71(11) . . ? O2 C6 C2 124.74(11) . . ? O3 C6 C2 112.55(10) . . ? O3 C7 H7B 109.4(10) . . ? O3 C7 H7C 106.0(13) . . ? H7B C7 H7C 111.8(16) . . ? O3 C7 H7A 108.4(12) . . ? H7B C7 H7A 112.2(16) . . ? H7C C7 H7A 108.8(17) . . ? O4 C8 C3 108.24(9) . . ? O4 C8 H8A 108.9(8) . . ? C3 C8 H8A 111.8(9) . . ? O4 C8 H8B 109.6(8) . . ? C3 C8 H8B 110.5(8) . . ? H8A C8 H8B 107.8(11) . . ? O5 C9 O4 123.79(11) . . ? O5 C9 C10 125.22(11) . . ? O4 C9 C10 110.98(10) . . ? C9 C10 H10B 111.3(11) . . ? C9 C10 H10C 110.7(11) . . ? H10B C10 H10C 112.2(15) . . ? C9 C10 H10A 108.9(11) . . ? H10B C10 H10A 106.7(15) . . ? H10C C10 H10A 106.8(15) . . ? C16 C11 C12 117.74(10) . . ? C16 C11 C4 119.76(10) . . ? C12 C11 C4 122.50(10) . . ? C13 C12 C11 120.80(11) . . ? C13 C12 H12 119.4(9) . . ? C11 C12 H12 119.7(9) . . ? C12 C13 C14 120.52(11) . . ? C12 C13 H13 120.0(9) . . ? C14 C13 H13 119.4(9) . . ? O6 C14 C13 116.38(10) . . ? O6 C14 C15 124.09(11) . . ? C13 C14 C15 119.53(11) . . ? C16 C15 C14 119.49(11) . . ? C16 C15 H15 121.2(9) . . ? C14 C15 H15 119.3(9) . . ? C15 C16 C11 121.87(10) . . ? C15 C16 H16 118.4(9) . . ? C11 C16 H16 119.8(9) . . ? O6 C17 H17A 111.2(9) . . ? O6 C17 H17B 112.0(10) . . ? H17A C17 H17B 112.2(13) . . ? O6 C17 H17C 106.7(10) . . ? H17A C17 H17C 109.1(12) . . ? H17B C17 H17C 105.3(13) . . ? 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 O1 C1 C2 0.18(12) . . . . ? C4 O1 C1 C5 -179.17(9) . . . . ? O1 C1 C2 C3 -0.34(12) . . . . ? C5 C1 C2 C3 178.81(12) . . . . ? O1 C1 C2 C6 178.15(10) . . . . ? C5 C1 C2 C6 -2.7(2) . . . . ? C1 C2 C3 C4 0.37(12) . . . . ? C6 C2 C3 C4 -178.16(10) . . . . ? C1 C2 C3 C8 -176.58(10) . . . . ? C6 C2 C3 C8 4.89(17) . . . . ? C2 C3 C4 O1 -0.26(12) . . . . ? C8 C3 C4 O1 176.65(10) . . . . ? C2 C3 C4 C11 -179.21(12) . . . . ? C8 C3 C4 C11 -2.3(2) . . . . ? C1 O1 C4 C3 0.06(12) . . . . ? C1 O1 C4 C11 179.25(9) . . . . ? C7 O3 C6 O2 3.35(17) . . . . ? C7 O3 C6 C2 -176.52(10) . . . . ? C1 C2 C6 O2 -171.99(12) . . . . ? C3 C2 C6 O2 6.23(19) . . . . ? C1 C2 C6 O3 7.87(16) . . . . ? C3 C2 C6 O3 -173.91(10) . . . . ? C9 O4 C8 C3 176.45(9) . . . . ? C4 C3 C8 O4 83.54(14) . . . . ? C2 C3 C8 O4 -100.15(12) . . . . ? C8 O4 C9 O5 0.62(16) . . . . ? C8 O4 C9 C10 179.90(10) . . . . ? C3 C4 C11 C16 169.13(12) . . . . ? O1 C4 C11 C16 -9.77(14) . . . . ? C3 C4 C11 C12 -10.6(2) . . . . ? O1 C4 C11 C12 170.46(9) . . . . ? C16 C11 C12 C13 -2.35(16) . . . . ? C4 C11 C12 C13 177.42(10) . . . . ? C11 C12 C13 C14 1.11(17) . . . . ? C17 O6 C14 C13 -178.45(10) . . . . ? C17 O6 C14 C15 0.52(16) . . . . ? C12 C13 C14 O6 -179.92(10) . . . . ? C12 C13 C14 C15 1.07(17) . . . . ? O6 C14 C15 C16 179.16(10) . . . . ? C13 C14 C15 C16 -1.91(17) . . . . ? C14 C15 C16 C11 0.61(17) . . . . ? C12 C11 C16 C15 1.50(16) . . . . ? C4 C11 C16 C15 -178.28(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.513 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.064