# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address C.Gregg ;School of Chemical and Physical Sciences Flinders University PO Box 2011 Adelaide 5001 Australia ; M.Perkins '' _publ_contact_author_address ;School of Chemical and Physical Sciences Flinders University PO Box 2011 Adelaide 5001 Australia ; _publ_contact_author_email mike.perkins@flinders.edu.au _publ_contact_author_fax '+61 8 8201 2905' _publ_contact_author_phone '+61 8 8201 2496' _publ_contact_author_name 'Michael V Perkins' data_cg1552 _database_code_depnum_ccdc_archive 'CCDC 870497' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O4' _chemical_formula_weight 252.30 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.8972(2) _cell_length_b 12.2375(3) _cell_length_c 12.7413(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1387.27(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5766 _cell_measurement_theta_min 2.2845 _cell_measurement_theta_max 30.0345 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_min 0.97047 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2413 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13678 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.10 _reflns_number_total 3664 _reflns_number_gt 2676 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_number_reflns 3664 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 0.86701(13) 0.99983(9) 0.65646(9) 0.0241(3) Uani 1 1 d . . . C4 C 0.87231(18) 0.77820(12) 0.64122(12) 0.0180(3) Uani 1 1 d . . . O7 O 1.01587(15) 0.99658(9) 0.79440(10) 0.0312(3) Uani 1 1 d . . . O9 O 0.86354(13) 0.67033(9) 0.62415(9) 0.0230(3) Uani 1 1 d . . . H9 H 0.9211 0.6375 0.6658 0.028 Uiso 1 1 calc R . . C2 C 0.95113(19) 0.94202(13) 0.72797(13) 0.0223(4) Uani 1 1 d . . . C3 C 0.95506(18) 0.82565(12) 0.71879(13) 0.0199(4) Uani 1 1 d . . . C11 C 0.7055(2) 1.03481(14) 0.51424(14) 0.0261(4) Uani 1 1 d . . . H11 H 0.6321 0.9956 0.4683 0.031 Uiso 1 1 calc R . . C5 C 0.78451(17) 0.84110(14) 0.56705(13) 0.0207(3) Uani 1 1 d . . . C10 C 0.7007(2) 0.78259(15) 0.48262(16) 0.0311(4) Uani 1 1 d . . . H10A H 0.6599 0.8359 0.4327 0.047 Uiso 1 1 calc R . . H10B H 0.6181 0.7407 0.5138 0.047 Uiso 1 1 calc R . . H10C H 0.7689 0.7327 0.4459 0.047 Uiso 1 1 calc R . . C12 C 0.6150(2) 1.11385(15) 0.58381(15) 0.0304(4) Uani 1 1 d . . . C8 C 1.0493(2) 0.76482(14) 0.79651(15) 0.0281(4) Uani 1 1 d . . . H8A H 0.9912 0.7527 0.8608 0.042 Uiso 1 1 calc R . . H8B H 1.1393 0.8077 0.8130 0.042 Uiso 1 1 calc R . . H8C H 1.0791 0.6943 0.7667 0.042 Uiso 1 1 calc R . . C6 C 0.78457(18) 0.95060(14) 0.57863(13) 0.0213(4) Uani 1 1 d . . . O17 O 0.61870(17) 1.21074(11) 0.56606(13) 0.0463(4) Uani 1 1 d . . . C16 C 0.8152(2) 1.09571(17) 0.44216(16) 0.0370(5) Uani 1 1 d . . . H16A H 0.8914 1.1327 0.4848 0.055 Uiso 1 1 calc R . . H16B H 0.7600 1.1499 0.4006 0.055 Uiso 1 1 calc R . . H16C H 0.8642 1.0435 0.3950 0.055 Uiso 1 1 calc R . . C13 C 0.5204(2) 1.06609(19) 0.67135(18) 0.0432(5) Uani 1 1 d . . . H13 H 0.5891 1.0158 0.7105 0.052 Uiso 1 1 calc R . . C14 C 0.3938(3) 0.9931(2) 0.6291(2) 0.0625(7) Uani 1 1 d . . . H14A H 0.4393 0.9317 0.5897 0.075 Uiso 1 1 calc R . . H14B H 0.3383 0.9617 0.6893 0.075 Uiso 1 1 calc R . . C15 C 0.2848(3) 1.0506(2) 0.5592(2) 0.0625(7) Uani 1 1 d . . . H15A H 0.2352 1.1093 0.5984 0.094 Uiso 1 1 calc R . . H15B H 0.2092 0.9985 0.5341 0.094 Uiso 1 1 calc R . . H15C H 0.3385 1.0818 0.4991 0.094 Uiso 1 1 calc R . . C18 C 0.4732(3) 1.1497(3) 0.7489(2) 0.0728(8) Uani 1 1 d . . . H18A H 0.5624 1.1827 0.7811 0.109 Uiso 1 1 calc R . . H18B H 0.4117 1.1152 0.8034 0.109 Uiso 1 1 calc R . . H18C H 0.4143 1.2065 0.7135 0.109 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 0.0319(6) 0.0158(5) 0.0246(6) 0.0005(5) -0.0070(5) 0.0017(5) C4 0.0180(8) 0.0166(7) 0.0195(8) 0.0000(6) 0.0046(7) 0.0018(6) O7 0.0471(7) 0.0186(5) 0.0279(6) -0.0011(6) -0.0141(6) -0.0030(6) O9 0.0263(6) 0.0161(5) 0.0267(6) -0.0018(5) -0.0067(5) 0.0015(5) C2 0.0273(9) 0.0197(8) 0.0201(8) 0.0010(7) -0.0024(7) 0.0014(7) C3 0.0220(9) 0.0177(7) 0.0200(8) 0.0015(7) 0.0010(7) 0.0005(6) C11 0.0292(9) 0.0223(8) 0.0269(9) 0.0010(7) -0.0067(8) 0.0001(7) C5 0.0178(8) 0.0234(8) 0.0209(8) -0.0008(7) -0.0002(7) 0.0013(7) C10 0.0364(11) 0.0250(9) 0.0320(10) -0.0032(8) -0.0154(9) 0.0009(8) C12 0.0271(9) 0.0282(9) 0.0358(10) -0.0016(8) -0.0114(9) 0.0072(8) C8 0.0389(10) 0.0218(8) 0.0237(9) 0.0001(7) -0.0106(8) 0.0022(7) C6 0.0211(8) 0.0238(8) 0.0191(8) 0.0009(7) -0.0025(7) 0.0017(7) O17 0.0535(9) 0.0243(7) 0.0611(10) -0.0013(7) -0.0077(9) 0.0103(6) C16 0.0424(11) 0.0381(11) 0.0304(10) 0.0118(9) -0.0014(9) 0.0030(9) C13 0.0363(11) 0.0535(13) 0.0399(12) -0.0006(10) 0.0037(10) 0.0136(10) C14 0.0541(14) 0.0608(16) 0.0724(18) 0.0148(15) 0.0175(14) 0.0049(13) C15 0.0488(14) 0.0648(17) 0.0738(18) 0.0117(15) -0.0003(15) 0.0032(12) C18 0.0658(18) 0.095(2) 0.0570(16) -0.0203(15) 0.0101(15) 0.0183(16) _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 C6 1.373(2) . ? O1 C2 1.3750(19) . ? C4 O9 1.3402(18) . ? C4 C3 1.362(2) . ? C4 C5 1.448(2) . ? O7 C2 1.2223(19) . ? O9 H9 0.8400 . ? C2 C3 1.429(2) . ? C3 C8 1.496(2) . ? C11 C6 1.493(2) . ? C11 C16 1.533(3) . ? C11 C12 1.539(3) . ? C11 H11 1.0000 . ? C5 C6 1.348(2) . ? C5 C10 1.492(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 O17 1.207(2) . ? C12 C13 1.515(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C13 C18 1.483(4) . ? C13 C14 1.535(4) . ? C13 H13 1.0000 . ? C14 C15 1.494(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C6 O1 C2 122.94(12) . . ? O9 C4 C3 124.69(14) . . ? O9 C4 C5 112.72(13) . . ? C3 C4 C5 122.59(14) . . ? C4 O9 H9 109.5 . . ? O7 C2 O1 115.74(13) . . ? O7 C2 C3 126.12(15) . . ? O1 C2 C3 118.14(14) . . ? C4 C3 C2 118.09(14) . . ? C4 C3 C8 124.82(14) . . ? C2 C3 C8 117.09(15) . . ? C6 C11 C16 111.38(14) . . ? C6 C11 C12 111.33(14) . . ? C16 C11 C12 111.85(16) . . ? C6 C11 H11 107.3 . . ? C16 C11 H11 107.3 . . ? C12 C11 H11 107.3 . . ? C6 C5 C4 117.18(15) . . ? C6 C5 C10 123.78(16) . . ? C4 C5 C10 119.03(14) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O17 C12 C13 122.13(19) . . ? O17 C12 C11 119.67(18) . . ? C13 C12 C11 118.18(16) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C6 O1 121.03(15) . . ? C5 C6 C11 128.73(16) . . ? O1 C6 C11 110.23(14) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C13 C12 112.5(2) . . ? C18 C13 C14 115.3(2) . . ? C12 C13 C14 111.97(19) . . ? C18 C13 H13 105.4 . . ? C12 C13 H13 105.4 . . ? C14 C13 H13 105.4 . . ? C15 C14 C13 114.3(2) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C6 O1 C2 O7 -178.32(15) . . . . ? C6 O1 C2 C3 1.5(2) . . . . ? O9 C4 C3 C2 -179.05(15) . . . . ? C5 C4 C3 C2 1.5(2) . . . . ? O9 C4 C3 C8 0.3(3) . . . . ? C5 C4 C3 C8 -179.15(16) . . . . ? O7 C2 C3 C4 178.23(16) . . . . ? O1 C2 C3 C4 -1.6(2) . . . . ? O7 C2 C3 C8 -1.1(3) . . . . ? O1 C2 C3 C8 179.09(14) . . . . ? O9 C4 C5 C6 179.16(15) . . . . ? C3 C4 C5 C6 -1.4(2) . . . . ? O9 C4 C5 C10 -1.2(2) . . . . ? C3 C4 C5 C10 178.25(16) . . . . ? C6 C11 C12 O17 136.57(18) . . . . ? C16 C11 C12 O17 11.2(2) . . . . ? C6 C11 C12 C13 -45.0(2) . . . . ? C16 C11 C12 C13 -170.33(16) . . . . ? C4 C5 C6 O1 1.2(2) . . . . ? C10 C5 C6 O1 -178.40(15) . . . . ? C4 C5 C6 C11 179.81(15) . . . . ? C10 C5 C6 C11 0.2(3) . . . . ? C2 O1 C6 C5 -1.4(2) . . . . ? C2 O1 C6 C11 179.80(15) . . . . ? C16 C11 C6 C5 -105.1(2) . . . . ? C12 C11 C6 C5 129.26(19) . . . . ? C16 C11 C6 O1 73.60(18) . . . . ? C12 C11 C6 O1 -52.00(18) . . . . ? O17 C12 C13 C18 -17.1(3) . . . . ? C11 C12 C13 C18 164.48(19) . . . . ? O17 C12 C13 C14 114.6(2) . . . . ? C11 C12 C13 C14 -63.8(2) . . . . ? C18 C13 C14 C15 69.6(3) . . . . ? C12 C13 C14 C15 -60.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.525 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.045 # Attachment '- Compound_23.cif' data_g:\cg7157~1\cg71572 _database_code_depnum_ccdc_archive 'CCDC 870498' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O4' _chemical_formula_weight 252.30 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.1642(3) _cell_length_b 12.0184(5) _cell_length_c 14.2772(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1400.89(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5417 _cell_measurement_theta_min 2.2106 _cell_measurement_theta_max 29.8536 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_min 0.98666 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2413 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10454 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 29.92 _reflns_number_total 3600 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(8) _refine_ls_number_reflns 3600 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 0.82913(12) 1.00271(8) 0.83739(6) 0.0200(2) Uani 1 1 d . . . O7 O 0.95125(12) 1.00410(8) 0.70003(7) 0.0241(2) Uani 1 1 d . . . O9 O 0.90502(12) 0.67315(8) 0.87828(7) 0.0233(2) Uani 1 1 d . . . H9 H 0.9567 0.6423 0.8345 0.028 Uiso 1 1 calc R . . C4 C 0.88805(16) 0.78163(11) 0.85956(9) 0.0175(3) Uani 1 1 d . . . C3 C 0.94393(16) 0.83181(11) 0.77969(8) 0.0183(3) Uani 1 1 d . . . C2 C 0.91188(17) 0.94746(11) 0.76771(9) 0.0180(3) Uani 1 1 d . . . C5 C 0.80523(16) 0.84257(11) 0.93257(9) 0.0187(3) Uani 1 1 d . . . C6 C 0.77815(16) 0.95130(11) 0.91808(9) 0.0169(3) Uani 1 1 d . . . C11 C 0.69765(17) 1.03470(11) 0.98184(9) 0.0203(3) Uani 1 1 d . . . H11 H 0.6406 0.9929 1.0328 0.024 Uiso 1 1 calc R . . O17 O 0.58282(14) 1.19878(9) 0.91382(9) 0.0376(3) Uani 1 1 d . . . C10 C 0.7607(2) 0.78227(13) 1.02129(10) 0.0306(4) Uani 1 1 d . . . H10A H 0.7178 0.8356 1.0671 0.046 Uiso 1 1 calc R . . H10B H 0.8583 0.7459 1.0469 0.046 Uiso 1 1 calc R . . H10C H 0.6770 0.7261 1.0077 0.046 Uiso 1 1 calc R . . C8 C 1.03773(19) 0.77333(12) 0.70439(10) 0.0263(3) Uani 1 1 d . . . H8A H 0.9631 0.7527 0.6535 0.039 Uiso 1 1 calc R . . H8B H 1.0885 0.7061 0.7302 0.039 Uiso 1 1 calc R . . H8C H 1.1231 0.8229 0.6801 0.039 Uiso 1 1 calc R . . C12 C 0.56797(18) 1.10003(12) 0.92672(9) 0.0238(3) Uani 1 1 d . . . C16 C 0.8243(2) 1.11109(14) 1.02724(11) 0.0305(4) Uani 1 1 d . . . H16A H 0.8806 1.1541 0.9786 0.046 Uiso 1 1 calc R . . H16B H 0.9044 1.0662 1.0617 0.046 Uiso 1 1 calc R . . H16C H 0.7693 1.1621 1.0706 0.046 Uiso 1 1 calc R . . C13 C 0.41868(19) 1.03709(14) 0.89482(12) 0.0364(4) Uani 1 1 d . . . H13 H 0.4491 0.9571 0.8865 0.044 Uiso 1 1 calc R . . C18 C 0.2875(2) 1.04516(15) 0.97189(15) 0.0404(4) Uani 1 1 d . . . H18A H 0.2588 1.1234 0.9821 0.061 Uiso 1 1 calc R . . H18B H 0.3304 1.0134 1.0301 0.061 Uiso 1 1 calc R . . H18C H 0.1897 1.0039 0.9525 0.061 Uiso 1 1 calc R . . C14 C 0.3540(2) 1.0814(2) 0.80188(14) 0.0569(6) Uani 1 1 d . . . H14A H 0.2470 1.0461 0.7884 0.068 Uiso 1 1 calc R . . H14B H 0.3358 1.1625 0.8076 0.068 Uiso 1 1 calc R . . C15 C 0.4693(3) 1.0597(4) 0.72027(16) 0.1132(15) Uani 1 1 d . . . H15A H 0.5014 0.9811 0.7200 0.170 Uiso 1 1 calc R . . H15B H 0.5672 1.1063 0.7269 0.170 Uiso 1 1 calc R . . H15C H 0.4138 1.0778 0.6613 0.170 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 0.0268(5) 0.0144(5) 0.0187(4) 0.0008(4) 0.0027(4) 0.0018(4) O7 0.0370(6) 0.0169(5) 0.0185(4) 0.0012(4) 0.0045(5) -0.0023(5) O9 0.0324(6) 0.0145(5) 0.0229(5) 0.0016(4) 0.0063(4) 0.0050(4) C4 0.0172(7) 0.0145(7) 0.0207(6) 0.0002(5) -0.0025(5) 0.0014(6) C3 0.0206(7) 0.0162(7) 0.0182(6) -0.0021(5) 0.0009(6) 0.0000(6) C2 0.0210(6) 0.0173(7) 0.0157(6) -0.0022(5) 0.0005(5) -0.0011(6) C5 0.0174(6) 0.0209(7) 0.0180(6) 0.0017(5) 0.0010(5) 0.0004(6) C6 0.0175(6) 0.0181(7) 0.0152(6) 0.0003(5) 0.0009(5) -0.0004(6) C11 0.0244(7) 0.0181(7) 0.0184(6) -0.0019(5) 0.0035(6) 0.0007(6) O17 0.0376(7) 0.0230(6) 0.0524(7) 0.0067(5) 0.0037(6) 0.0093(5) C10 0.0428(9) 0.0231(7) 0.0259(7) 0.0063(6) 0.0134(7) 0.0081(7) C8 0.0356(9) 0.0196(7) 0.0235(7) 0.0008(6) 0.0103(7) 0.0020(7) C12 0.0253(7) 0.0237(8) 0.0224(7) -0.0044(6) 0.0059(6) 0.0084(6) C16 0.0334(8) 0.0305(8) 0.0276(7) -0.0102(7) -0.0017(7) -0.0006(7) C13 0.0281(8) 0.0327(9) 0.0483(9) -0.0136(8) -0.0051(8) 0.0100(8) C18 0.0277(8) 0.0342(9) 0.0593(11) 0.0091(9) 0.0044(8) 0.0025(7) C14 0.0355(10) 0.0929(17) 0.0423(10) -0.0187(11) -0.0117(9) 0.0180(11) C15 0.0697(17) 0.235(5) 0.0354(12) -0.0227(18) -0.0089(12) 0.065(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.3720(16) . ? O1 C2 1.3737(15) . ? O7 C2 1.2250(16) . ? O9 C4 1.3381(17) . ? O9 H9 0.8400 . ? C4 C3 1.3682(17) . ? C4 C5 1.4423(18) . ? C3 C2 1.4246(19) . ? C3 C8 1.4954(18) . ? C5 C6 1.3414(19) . ? C5 C10 1.5039(19) . ? C6 C11 1.5051(18) . ? C11 C16 1.527(2) . ? C11 C12 1.535(2) . ? C11 H11 1.0000 . ? O17 C12 1.2072(18) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C12 C13 1.505(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C13 C14 1.524(3) . ? C13 C18 1.539(3) . ? C13 H13 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C14 C15 1.520(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C6 O1 C2 122.65(10) . . ? C4 O9 H9 109.5 . . ? O9 C4 C3 124.15(12) . . ? O9 C4 C5 113.51(11) . . ? C3 C4 C5 122.34(12) . . ? C4 C3 C2 117.96(11) . . ? C4 C3 C8 124.25(12) . . ? C2 C3 C8 117.80(11) . . ? O7 C2 O1 115.57(11) . . ? O7 C2 C3 126.07(12) . . ? O1 C2 C3 118.36(11) . . ? C6 C5 C4 117.42(12) . . ? C6 C5 C10 124.02(12) . . ? C4 C5 C10 118.51(12) . . ? C5 C6 O1 121.22(12) . . ? C5 C6 C11 128.87(12) . . ? O1 C6 C11 109.90(10) . . ? C6 C11 C16 111.18(11) . . ? C6 C11 C12 109.37(11) . . ? C16 C11 C12 112.16(12) . . ? C6 C11 H11 108.0 . . ? C16 C11 H11 108.0 . . ? C12 C11 H11 108.0 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O17 C12 C13 121.96(14) . . ? O17 C12 C11 120.78(14) . . ? C13 C12 C11 117.17(13) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C13 C14 111.61(16) . . ? C12 C13 C18 108.41(13) . . ? C14 C13 C18 111.07(14) . . ? C12 C13 H13 108.6 . . ? C14 C13 H13 108.6 . . ? C18 C13 H13 108.6 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C14 C13 113.13(16) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 O9 C4 C3 C2 177.78(12) . . . . ? C5 C4 C3 C2 -2.72(19) . . . . ? O9 C4 C3 C8 -2.7(2) . . . . ? C5 C4 C3 C8 176.78(12) . . . . ? C6 O1 C2 O7 -179.32(12) . . . . ? C6 O1 C2 C3 0.77(18) . . . . ? C4 C3 C2 O7 -178.90(13) . . . . ? C8 C3 C2 O7 1.6(2) . . . . ? C4 C3 C2 O1 1.01(18) . . . . ? C8 C3 C2 O1 -178.52(12) . . . . ? O9 C4 C5 C6 -177.82(12) . . . . ? C3 C4 C5 C6 2.63(19) . . . . ? O9 C4 C5 C10 4.59(18) . . . . ? C3 C4 C5 C10 -174.96(14) . . . . ? C4 C5 C6 O1 -0.79(19) . . . . ? C10 C5 C6 O1 176.66(13) . . . . ? C4 C5 C6 C11 -179.05(13) . . . . ? C10 C5 C6 C11 -1.6(2) . . . . ? C2 O1 C6 C5 -0.86(19) . . . . ? C2 O1 C6 C11 177.70(11) . . . . ? C5 C6 C11 C16 104.50(17) . . . . ? O1 C6 C11 C16 -73.92(14) . . . . ? C5 C6 C11 C12 -131.10(15) . . . . ? O1 C6 C11 C12 50.48(14) . . . . ? C6 C11 C12 O17 -115.50(15) . . . . ? C16 C11 C12 O17 8.33(19) . . . . ? C6 C11 C12 C13 67.92(15) . . . . ? C16 C11 C12 C13 -168.25(13) . . . . ? O17 C12 C13 C14 36.2(2) . . . . ? C11 C12 C13 C14 -147.26(13) . . . . ? O17 C12 C13 C18 -86.43(19) . . . . ? C11 C12 C13 C18 90.10(15) . . . . ? C12 C13 C14 C15 67.4(3) . . . . ? C18 C13 C14 C15 -171.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.038