# Electronic Supplementary Material (ESI) for Chemical Communications # 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_mo_dm11258_0m _database_code_depnum_ccdc_archive 'CCDC 856081' #TrackingRef 'mo_dm11258_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O2' _chemical_formula_weight 252.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5424(11) _cell_length_b 14.963(2) _cell_length_c 10.6477(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.882(2) _cell_angle_gamma 90.00 _cell_volume 1279.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5173 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.62 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9670 _exptl_absorpt_correction_T_max 0.9735 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 9120 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2777 _reflns_number_gt 2453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.5662P] 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 2777 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.83265(9) 0.04029(5) 0.34675(8) 0.01986(18) Uani 1 1 d . . . O2 O 0.67005(9) 0.16213(5) 0.28606(7) 0.01799(18) Uani 1 1 d . . . C1 C 0.96359(13) 0.06056(8) 0.30299(11) 0.0192(2) Uani 1 1 d . . . C2 C 0.99614(14) -0.00210(8) 0.21875(12) 0.0240(3) Uani 1 1 d . . . H2 H 0.9277 -0.0535 0.1917 0.029 Uiso 1 1 calc R . . C3 C 1.12973(15) 0.01115(9) 0.17437(12) 0.0295(3) Uani 1 1 d . . . H3 H 1.1531 -0.0314 0.1169 0.035 Uiso 1 1 calc R . . C4 C 1.22891(15) 0.08649(10) 0.21395(13) 0.0304(3) Uani 1 1 d . . . H4 H 1.3209 0.0954 0.1844 0.037 Uiso 1 1 calc R . . C5 C 1.19346(14) 0.14878(9) 0.29676(12) 0.0260(3) Uani 1 1 d . . . H5 H 1.2618 0.2003 0.3232 0.031 Uiso 1 1 calc R . . C6 C 1.05939(13) 0.13748(8) 0.34230(11) 0.0204(2) Uani 1 1 d . . . C7 C 1.01306(14) 0.20701(8) 0.42533(12) 0.0214(2) Uani 1 1 d . . . H7A H 0.9560 0.2572 0.3671 0.026 Uiso 1 1 calc R . . H7B H 1.1156 0.2308 0.4926 0.026 Uiso 1 1 calc R . . C8 C 0.89941(13) 0.16950(7) 0.49646(11) 0.0191(2) Uani 1 1 d . . . H8 H 0.9677 0.1325 0.5739 0.023 Uiso 1 1 calc R . . C9 C 0.81457(14) 0.24407(8) 0.54837(11) 0.0220(2) Uani 1 1 d . . . H9A H 0.7725 0.2195 0.6172 0.026 Uiso 1 1 calc R . . H9B H 0.8970 0.2912 0.5906 0.026 Uiso 1 1 calc R . . C10 C 0.67163(13) 0.28452(7) 0.43669(11) 0.0192(2) Uani 1 1 d . . . C11 C 0.59779(15) 0.36503(8) 0.45335(12) 0.0243(3) Uani 1 1 d . . . H11 H 0.6373 0.3946 0.5372 0.029 Uiso 1 1 calc R . . C12 C 0.46824(15) 0.40249(8) 0.35019(13) 0.0268(3) Uani 1 1 d . . . H12 H 0.4187 0.4568 0.3639 0.032 Uiso 1 1 calc R . . C13 C 0.41082(14) 0.36038(8) 0.22643(12) 0.0246(3) Uani 1 1 d . . . H13 H 0.3231 0.3864 0.1551 0.029 Uiso 1 1 calc R . . C14 C 0.48148(14) 0.28066(8) 0.20725(11) 0.0205(2) Uani 1 1 d . . . H14 H 0.4432 0.2520 0.1226 0.025 Uiso 1 1 calc R . . C15 C 0.60899(13) 0.24256(7) 0.31265(11) 0.0173(2) Uani 1 1 d . . . C16 C 0.76555(13) 0.11049(7) 0.40165(11) 0.0174(2) Uani 1 1 d . . . C17 C 0.64990(14) 0.06654(8) 0.46378(12) 0.0212(2) Uani 1 1 d . . . H17A H 0.5704 0.0284 0.3974 0.032 Uiso 1 1 calc R . . H17B H 0.5894 0.1127 0.4940 0.032 Uiso 1 1 calc R . . H17C H 0.7151 0.0301 0.5402 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0182(4) 0.0181(4) 0.0256(4) -0.0010(3) 0.0104(3) 0.0002(3) O2 0.0188(4) 0.0180(4) 0.0162(4) -0.0002(3) 0.0047(3) 0.0020(3) C1 0.0150(5) 0.0238(6) 0.0185(5) 0.0045(4) 0.0051(4) 0.0037(4) C2 0.0220(5) 0.0270(6) 0.0217(6) 0.0004(5) 0.0058(5) 0.0048(5) C3 0.0261(6) 0.0412(7) 0.0227(6) 0.0007(5) 0.0103(5) 0.0105(5) C4 0.0208(6) 0.0455(8) 0.0284(6) 0.0084(6) 0.0129(5) 0.0058(5) C5 0.0176(5) 0.0331(6) 0.0263(6) 0.0075(5) 0.0065(5) 0.0004(5) C6 0.0161(5) 0.0249(6) 0.0186(5) 0.0056(4) 0.0039(4) 0.0029(4) C7 0.0175(5) 0.0220(5) 0.0227(6) 0.0002(4) 0.0041(4) -0.0027(4) C8 0.0173(5) 0.0210(5) 0.0173(5) 0.0009(4) 0.0036(4) 0.0010(4) C9 0.0231(6) 0.0241(6) 0.0171(5) -0.0031(4) 0.0047(4) 0.0006(4) C10 0.0192(5) 0.0198(5) 0.0199(5) 0.0001(4) 0.0082(4) -0.0009(4) C11 0.0281(6) 0.0212(6) 0.0258(6) -0.0025(5) 0.0122(5) -0.0003(5) C12 0.0279(6) 0.0185(5) 0.0367(7) 0.0018(5) 0.0144(5) 0.0041(5) C13 0.0204(5) 0.0223(6) 0.0299(6) 0.0076(5) 0.0072(5) 0.0026(4) C14 0.0185(5) 0.0225(5) 0.0204(5) 0.0020(4) 0.0064(4) -0.0025(4) C15 0.0167(5) 0.0161(5) 0.0211(5) 0.0015(4) 0.0092(4) -0.0004(4) C16 0.0168(5) 0.0178(5) 0.0180(5) 0.0017(4) 0.0062(4) 0.0026(4) C17 0.0198(5) 0.0220(5) 0.0238(6) 0.0030(4) 0.0099(4) 0.0002(4) _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 1.3837(13) . ? O1 C16 1.4147(13) . ? O2 C15 1.3787(13) . ? O2 C16 1.4473(13) . ? C1 C2 1.3895(16) . ? C1 C6 1.3917(16) . ? C2 C3 1.3898(17) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.3855(19) . ? C4 H4 0.9500 . ? C5 C6 1.3976(16) . ? C5 H5 0.9500 . ? C6 C7 1.5029(16) . ? C7 C8 1.5268(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C16 1.5236(15) . ? C8 C9 1.5323(15) . ? C8 H8 1.0000 . ? C9 C10 1.5113(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.3943(16) . ? C10 C11 1.3987(16) . ? C11 C12 1.3851(17) . ? C11 H11 0.9500 . ? C12 C13 1.3908(18) . ? C12 H12 0.9500 . ? C13 C14 1.3830(16) . ? C13 H13 0.9500 . ? C14 C15 1.3927(16) . ? C14 H14 0.9500 . ? C16 C17 1.5134(15) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C16 117.64(8) . . ? C15 O2 C16 115.76(8) . . ? O1 C1 C2 115.58(10) . . ? O1 C1 C6 122.68(10) . . ? C2 C1 C6 121.73(10) . . ? C1 C2 C3 119.41(12) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.00(12) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.81(11) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.45(12) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 117.59(11) . . ? C1 C6 C7 120.26(10) . . ? C5 C6 C7 122.09(11) . . ? C6 C7 C8 112.11(9) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C16 C8 C7 110.18(9) . . ? C16 C8 C9 108.70(9) . . ? C7 C8 C9 111.70(9) . . ? C16 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C10 C9 C8 111.25(9) . . ? 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 . . ? C15 C10 C11 117.62(10) . . ? C15 C10 C9 120.80(10) . . ? C11 C10 C9 121.58(10) . . ? C12 C11 C10 121.41(11) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 119.81(11) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 119.98(11) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.67(11) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? O2 C15 C14 116.02(10) . . ? O2 C15 C10 122.51(10) . . ? C14 C15 C10 121.47(10) . . ? O1 C16 O2 103.62(8) . . ? O1 C16 C17 105.93(9) . . ? O2 C16 C17 109.92(9) . . ? O1 C16 C8 112.70(9) . . ? O2 C16 C8 109.45(9) . . ? C17 C16 C8 114.62(9) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.282 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.043 data_cd211326 _database_code_depnum_ccdc_archive 'CCDC 856082' #TrackingRef 'cd211326.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 O2' _chemical_formula_weight 280.35 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 Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 31.4581(18) _cell_length_b 31.4581(18) _cell_length_c 8.0818(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6926.3(8) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1754 _cell_measurement_theta_min 4.486 _cell_measurement_theta_max 47.516 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.257 _exptl_crystal_size_mid 0.165 _exptl_crystal_size_min 0.098 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2700 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.38194 _exptl_absorpt_correction_T_max 1.00000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12654 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3009 _reflns_number_gt 1937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.0285P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00040(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3009 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.50934(4) 0.09677(3) 0.41908(12) 0.0580(3) Uani 1 1 d . . . O2 O 0.54082(3) 0.10805(3) 0.15206(12) 0.0584(3) Uani 1 1 d . . . C1 C 0.53580(5) 0.14297(5) 0.48784(19) 0.0524(4) Uani 1 1 d . . . C2 C 0.55320(5) 0.14454(6) 0.64628(19) 0.0622(4) Uani 1 1 d . . . H2 H 0.5470 0.1157 0.6990 0.075 Uiso 1 1 calc R . . C3 C 0.57974(6) 0.18889(8) 0.7252(2) 0.0774(5) Uani 1 1 d . . . H3 H 0.5915 0.1901 0.8318 0.093 Uiso 1 1 calc R . . C4 C 0.58899(6) 0.23145(7) 0.6467(3) 0.0815(6) Uani 1 1 d . . . H4 H 0.6074 0.2615 0.6995 0.098 Uiso 1 1 calc R . . C5 C 0.57096(6) 0.22947(6) 0.4896(2) 0.0710(5) Uani 1 1 d . . . H5 H 0.5772 0.2584 0.4377 0.085 Uiso 1 1 calc R . . C6 C 0.54368(5) 0.18500(6) 0.4071(2) 0.0566(4) Uani 1 1 d . . . C7 C 0.52198(6) 0.18140(6) 0.2385(2) 0.0659(5) Uani 1 1 d . . . H7A H 0.5474 0.1910 0.1555 0.079 Uiso 1 1 calc R . . H7B H 0.5095 0.2040 0.2318 0.079 Uiso 1 1 calc R . . C8 C 0.48061(6) 0.12960(5) 0.20210(19) 0.0575(4) Uani 1 1 d . . . H8 H 0.4530 0.1231 0.2745 0.069 Uiso 1 1 calc R . . C9 C 0.49718(5) 0.09323(5) 0.24688(17) 0.0525(4) Uani 1 1 d . . . C10 C 0.46095(5) 0.03919(5) 0.21648(19) 0.0592(4) Uani 1 1 d . . . H10 H 0.4559 0.0348 0.0966 0.071 Uiso 1 1 calc R . . C11 C 0.48339(6) 0.00867(6) 0.2719(2) 0.0682(5) Uani 1 1 d . . . H11A H 0.4827 0.0069 0.3918 0.082 Uiso 1 1 calc R . . H11B H 0.4638 -0.0244 0.2293 0.082 Uiso 1 1 calc R . . C12 C 0.53535(6) 0.02989(6) 0.21286(19) 0.0592(4) Uani 1 1 d . . . C13 C 0.55963(7) 0.00343(6) 0.2130(2) 0.0730(5) Uani 1 1 d . . . H13 H 0.5442 -0.0280 0.2578 0.088 Uiso 1 1 calc R . . C14 C 0.60606(8) 0.02254(8) 0.1484(2) 0.0807(6) Uani 1 1 d . . . H14 H 0.6219 0.0043 0.1512 0.097 Uiso 1 1 calc R . . C15 C 0.62916(6) 0.06884(8) 0.0795(2) 0.0771(5) Uani 1 1 d . . . H15 H 0.6601 0.0813 0.0323 0.093 Uiso 1 1 calc R . . C16 C 0.60636(6) 0.09665(6) 0.0805(2) 0.0642(4) Uani 1 1 d . . . H16 H 0.6218 0.1279 0.0346 0.077 Uiso 1 1 calc R . . C17 C 0.56030(6) 0.07732(6) 0.15090(18) 0.0544(4) Uani 1 1 d . . . C18 C 0.46285(6) 0.12461(7) 0.0234(2) 0.0782(5) Uani 1 1 d . . . H18A H 0.4533 0.1487 0.0018 0.117 Uiso 1 1 calc R . . H18B H 0.4352 0.0924 0.0067 0.117 Uiso 1 1 calc R . . H18C H 0.4889 0.1296 -0.0505 0.117 Uiso 1 1 calc R . . C19 C 0.41074(6) 0.02099(6) 0.2951(2) 0.0780(5) Uani 1 1 d . . . H19A H 0.3898 -0.0132 0.2700 0.117 Uiso 1 1 calc R . . H19B H 0.3964 0.0394 0.2520 0.117 Uiso 1 1 calc R . . H19C H 0.4143 0.0253 0.4129 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0669(7) 0.0557(6) 0.0466(6) -0.0032(5) -0.0064(5) 0.0271(5) O2 0.0581(7) 0.0606(6) 0.0578(7) 0.0048(5) 0.0059(5) 0.0308(5) C1 0.0470(9) 0.0562(10) 0.0523(10) -0.0082(8) 0.0007(7) 0.0246(7) C2 0.0563(10) 0.0703(11) 0.0525(10) -0.0063(8) -0.0022(8) 0.0261(9) C3 0.0689(12) 0.0935(14) 0.0618(12) -0.0178(11) -0.0083(9) 0.0347(11) C4 0.0704(12) 0.0776(13) 0.0872(15) -0.0332(12) -0.0091(11) 0.0299(10) C5 0.0637(11) 0.0607(11) 0.0875(14) -0.0089(10) 0.0015(10) 0.0302(9) C6 0.0515(9) 0.0575(10) 0.0629(11) -0.0072(8) 0.0001(8) 0.0288(8) C7 0.0722(11) 0.0634(10) 0.0691(12) 0.0021(8) -0.0028(9) 0.0393(9) C8 0.0566(9) 0.0662(10) 0.0525(10) -0.0001(8) -0.0023(7) 0.0327(8) C9 0.0533(9) 0.0602(10) 0.0415(9) 0.0002(7) 0.0006(7) 0.0266(8) C10 0.0594(10) 0.0602(10) 0.0507(10) -0.0074(7) -0.0016(8) 0.0245(8) C11 0.0745(11) 0.0571(10) 0.0661(11) -0.0045(8) -0.0012(9) 0.0277(9) C12 0.0709(11) 0.0586(10) 0.0508(10) -0.0132(8) -0.0105(8) 0.0343(9) C13 0.0864(14) 0.0678(11) 0.0723(12) -0.0194(9) -0.0196(10) 0.0441(11) C14 0.0858(14) 0.0887(15) 0.0869(15) -0.0336(11) -0.0270(11) 0.0582(12) C15 0.0644(11) 0.1001(15) 0.0731(13) -0.0291(11) -0.0136(9) 0.0457(12) C16 0.0605(10) 0.0749(11) 0.0564(11) -0.0128(8) -0.0078(8) 0.0332(9) C17 0.0577(10) 0.0636(10) 0.0460(9) -0.0119(7) -0.0092(7) 0.0335(9) C18 0.0803(12) 0.0924(13) 0.0680(12) 0.0034(10) -0.0122(9) 0.0478(10) C19 0.0630(11) 0.0699(11) 0.0822(13) -0.0070(10) 0.0062(9) 0.0191(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3800(16) . ? O1 C9 1.4328(16) . ? O2 C17 1.3792(17) . ? O2 C9 1.4315(16) . ? C1 C6 1.381(2) . ? C1 C2 1.384(2) . ? C2 C3 1.373(2) . ? C2 H2 0.9300 . ? C3 C4 1.375(2) . ? C3 H3 0.9300 . ? C4 C5 1.380(2) . ? C4 H4 0.9300 . ? C5 C6 1.392(2) . ? C5 H5 0.9300 . ? C6 C7 1.503(2) . ? C7 C8 1.521(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.5192(19) . ? C8 C18 1.528(2) . ? C8 H8 0.9800 . ? C9 C10 1.5206(19) . ? C10 C11 1.516(2) . ? C10 C19 1.524(2) . ? C10 H10 0.9800 . ? C11 C12 1.501(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.383(2) . ? C12 C17 1.386(2) . ? C13 C14 1.374(2) . ? C13 H13 0.9300 . ? C14 C15 1.379(2) . ? C14 H14 0.9300 . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 C17 1.383(2) . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C1 O1 C9 118.03(11) . . ? C17 O2 C9 117.73(11) . . ? O1 C1 C6 122.90(14) . . ? O1 C1 C2 115.45(14) . . ? C6 C1 C2 121.64(14) . . ? C3 C2 C1 119.66(17) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.01(17) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.91(17) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 121.28(17) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.48(15) . . ? C1 C6 C7 119.92(14) . . ? C5 C6 C7 122.59(15) . . ? C6 C7 C8 111.66(13) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 109.20(12) . . ? C9 C8 C18 113.15(13) . . ? C7 C8 C18 111.46(13) . . ? C9 C8 H8 107.6 . . ? C7 C8 H8 107.6 . . ? C18 C8 H8 107.6 . . ? O2 C9 O1 108.62(11) . . ? O2 C9 C8 105.16(11) . . ? O1 C9 C8 110.59(11) . . ? O2 C9 C10 109.77(11) . . ? O1 C9 C10 105.40(11) . . ? C8 C9 C10 117.12(12) . . ? C11 C10 C9 109.52(12) . . ? C11 C10 C19 111.24(13) . . ? C9 C10 C19 114.17(13) . . ? C11 C10 H10 107.2 . . ? C9 C10 H10 107.2 . . ? C19 C10 H10 107.2 . . ? C12 C11 C10 111.88(13) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C17 117.52(16) . . ? C13 C12 C11 122.57(16) . . ? C17 C12 C11 119.88(14) . . ? C14 C13 C12 121.49(18) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.95(17) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.01(18) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 119.08(17) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? O2 C17 C16 115.45(14) . . ? O2 C17 C12 122.75(14) . . ? C16 C17 C12 121.80(15) . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C9 O1 C1 C6 11.40(19) . . . . ? C9 O1 C1 C2 -170.08(12) . . . . ? O1 C1 C2 C3 -179.69(13) . . . . ? C6 C1 C2 C3 -1.1(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? O1 C1 C6 C5 179.99(13) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? O1 C1 C6 C7 1.5(2) . . . . ? C2 C1 C6 C7 -176.93(14) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C4 C5 C6 C7 177.72(15) . . . . ? C1 C6 C7 C8 18.0(2) . . . . ? C5 C6 C7 C8 -160.41(14) . . . . ? C6 C7 C8 C9 -47.37(17) . . . . ? C6 C7 C8 C18 -173.11(13) . . . . ? C17 O2 C9 O1 70.33(14) . . . . ? C17 O2 C9 C8 -171.26(11) . . . . ? C17 O2 C9 C10 -44.44(16) . . . . ? C1 O1 C9 O2 72.43(14) . . . . ? C1 O1 C9 C8 -42.50(16) . . . . ? C1 O1 C9 C10 -169.98(11) . . . . ? C7 C8 C9 O2 -56.84(15) . . . . ? C18 C8 C9 O2 67.93(15) . . . . ? C7 C8 C9 O1 60.25(15) . . . . ? C18 C8 C9 O1 -174.99(13) . . . . ? C7 C8 C9 C10 -179.02(12) . . . . ? C18 C8 C9 C10 -54.25(18) . . . . ? O2 C9 C10 C11 61.50(15) . . . . ? O1 C9 C10 C11 -55.30(15) . . . . ? C8 C9 C10 C11 -178.73(13) . . . . ? O2 C9 C10 C19 -173.01(12) . . . . ? O1 C9 C10 C19 70.18(16) . . . . ? C8 C9 C10 C19 -53.25(19) . . . . ? C9 C10 C11 C12 -45.66(17) . . . . ? C19 C10 C11 C12 -172.81(13) . . . . ? C10 C11 C12 C13 -164.37(14) . . . . ? C10 C11 C12 C17 13.8(2) . . . . ? C17 C12 C13 C14 -2.5(2) . . . . ? C11 C12 C13 C14 175.70(15) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C13 C14 C15 C16 2.3(3) . . . . ? C14 C15 C16 C17 -0.2(2) . . . . ? C9 O2 C17 C16 -169.93(12) . . . . ? C9 O2 C17 C12 11.24(19) . . . . ? C15 C16 C17 O2 177.85(13) . . . . ? C15 C16 C17 C12 -3.3(2) . . . . ? C13 C12 C17 O2 -176.65(13) . . . . ? C11 C12 C17 O2 5.1(2) . . . . ? C13 C12 C17 C16 4.6(2) . . . . ? C11 C12 C17 C16 -173.63(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.114 _refine_diff_density_min -0.105 _refine_diff_density_rms 0.024