# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_new #TrackingRef 'SJG-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 O3' _chemical_formula_weight 330.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.1432(3) _cell_length_b 8.1265(2) _cell_length_c 20.3620(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.036(2) _cell_angle_gamma 90.00 _cell_volume 1665.77(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3496 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 26.83 _exptl_crystal_description Block _exptl_crystal_colour clear _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9786 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 12682 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.45 _reflns_number_total 4171 _reflns_number_gt 2577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0628P)^2^+0.5207P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4171 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.5973(2) -0.2914(3) 0.47758(12) 0.0621(6) Uani 1 1 d . . . H1A H 0.6788 -0.2603 0.5047 0.074 Uiso 1 1 calc R . . H1B H 0.6121 -0.3953 0.4562 0.074 Uiso 1 1 calc R . . C2 C 0.39024(18) -0.2155(2) 0.48706(10) 0.0495(5) Uani 1 1 d . . . C3 C 0.2645(2) -0.2004(3) 0.50357(11) 0.0619(6) Uani 1 1 d . . . H3 H 0.2368 -0.2561 0.5393 0.074 Uiso 1 1 calc R . . C4 C 0.17935(19) -0.0951(3) 0.46302(11) 0.0620(6) Uani 1 1 d . . . H4 H 0.0922 -0.0819 0.4720 0.074 Uiso 1 1 calc R . . C5 C 0.22091(19) -0.0109(2) 0.41048(10) 0.0512(5) Uani 1 1 d . . . C6 C 0.34906(19) -0.0277(3) 0.39580(10) 0.0541(5) Uani 1 1 d . . . H6 H 0.3788 0.0297 0.3609 0.065 Uiso 1 1 calc R . . C7 C 0.43121(18) -0.1322(2) 0.43451(10) 0.0499(5) Uani 1 1 d . . . C8 C 0.12644(19) 0.0996(2) 0.36746(10) 0.0534(5) Uani 1 1 d . . . H8 H 0.1739 0.1459 0.3326 0.064 Uiso 1 1 calc R . . C9 C 0.00372(18) 0.0140(2) 0.33523(10) 0.0513(5) Uani 1 1 d . . . H9A H -0.0486 -0.0248 0.3689 0.062 Uiso 1 1 calc R . . H9B H 0.0288 -0.0805 0.3104 0.062 Uiso 1 1 calc R . . C10 C -0.07886(17) 0.1331(2) 0.28873(9) 0.0477(5) Uani 1 1 d . . . H10 H -0.0261 0.1597 0.2529 0.057 Uiso 1 1 calc R . . C11 C -0.09693(17) 0.2919(2) 0.32573(10) 0.0470(4) Uani 1 1 d . . . C12 C -0.1968(2) 0.4032(3) 0.30473(12) 0.0613(6) Uani 1 1 d . . . H12 H -0.2571 0.3779 0.2679 0.074 Uiso 1 1 calc R . . C13 C -0.2091(2) 0.5504(3) 0.33697(15) 0.0761(7) Uani 1 1 d . . . H13 H -0.2775 0.6226 0.3223 0.091 Uiso 1 1 calc R . . C14 C -0.1205(2) 0.5899(3) 0.39047(15) 0.0744(7) Uani 1 1 d . . . H14 H -0.1281 0.6900 0.4119 0.089 Uiso 1 1 calc R . . C15 C -0.0199(2) 0.4830(3) 0.41308(12) 0.0609(6) Uani 1 1 d . . . H15 H 0.0408 0.5111 0.4493 0.073 Uiso 1 1 calc R . . C16 C -0.00952(18) 0.3331(2) 0.38156(10) 0.0482(5) Uani 1 1 d . . . C17 C -0.20793(17) 0.0562(2) 0.25680(9) 0.0466(5) Uani 1 1 d . . . C18 C -0.29974(19) -0.0132(3) 0.29289(11) 0.0592(5) Uani 1 1 d . . . H18 H -0.2856 -0.0089 0.3389 0.071 Uiso 1 1 calc R . . C19 C -0.4122(2) -0.0888(3) 0.26209(13) 0.0701(7) Uani 1 1 d . . . H19 H -0.4724 -0.1367 0.2873 0.084 Uiso 1 1 calc R . . C20 C -0.4354(2) -0.0937(3) 0.19415(14) 0.0716(7) Uani 1 1 d . . . H20 H -0.5105 -0.1463 0.1733 0.086 Uiso 1 1 calc R . . C21 C -0.3476(2) -0.0208(3) 0.15765(12) 0.0738(7) Uani 1 1 d . . . H21 H -0.3641 -0.0213 0.1117 0.089 Uiso 1 1 calc R . . C22 C -0.2342(2) 0.0537(3) 0.18859(11) 0.0609(6) Uani 1 1 d . . . H22 H -0.1749 0.1027 0.1632 0.073 Uiso 1 1 calc R . . O1 O 0.56151(14) -0.1689(2) 0.42923(8) 0.0708(5) Uani 1 1 d . . . O2 O 0.49317(14) -0.30821(19) 0.51753(7) 0.0644(4) Uani 1 1 d . . . O3 O 0.09065(13) 0.23256(17) 0.40879(7) 0.0578(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0488(10) 0.0644(14) 0.0709(14) 0.0044(12) -0.0010(10) 0.0051(10) C2 0.0474(10) 0.0473(11) 0.0517(11) 0.0017(9) -0.0020(8) -0.0019(8) C3 0.0558(11) 0.0690(14) 0.0617(13) 0.0100(11) 0.0098(10) -0.0037(10) C4 0.0403(10) 0.0710(14) 0.0745(15) -0.0025(12) 0.0064(10) 0.0017(9) C5 0.0516(10) 0.0470(11) 0.0531(12) -0.0021(9) -0.0016(9) -0.0026(9) C6 0.0539(11) 0.0521(12) 0.0552(12) 0.0047(9) 0.0015(9) -0.0013(9) C7 0.0480(10) 0.0467(11) 0.0536(11) -0.0007(9) 0.0000(8) -0.0014(8) C8 0.0515(10) 0.0481(11) 0.0595(12) -0.0013(10) 0.0028(9) 0.0042(8) C9 0.0493(10) 0.0421(10) 0.0595(12) -0.0073(9) -0.0052(9) 0.0071(8) C10 0.0454(9) 0.0482(11) 0.0497(11) -0.0001(9) 0.0059(8) 0.0053(8) C11 0.0442(9) 0.0391(10) 0.0585(12) 0.0026(9) 0.0100(8) 0.0020(7) C12 0.0542(11) 0.0492(12) 0.0805(15) 0.0057(11) 0.0082(11) 0.0088(9) C13 0.0668(14) 0.0449(13) 0.119(2) 0.0060(14) 0.0227(15) 0.0135(11) C14 0.0751(15) 0.0389(12) 0.115(2) -0.0141(13) 0.0357(15) -0.0030(11) C15 0.0657(13) 0.0471(12) 0.0733(15) -0.0118(11) 0.0214(11) -0.0096(10) C16 0.0476(10) 0.0396(10) 0.0591(12) -0.0028(9) 0.0134(9) -0.0022(8) C17 0.0446(9) 0.0424(10) 0.0511(11) -0.0020(8) -0.0015(8) 0.0100(8) C18 0.0548(11) 0.0688(14) 0.0529(12) 0.0044(11) 0.0018(9) 0.0025(10) C19 0.0525(12) 0.0704(15) 0.0870(18) 0.0050(13) 0.0065(12) 0.0008(11) C20 0.0524(12) 0.0715(16) 0.0856(18) -0.0161(14) -0.0122(12) 0.0038(11) C21 0.0755(15) 0.0861(18) 0.0548(13) -0.0173(13) -0.0126(12) 0.0121(13) C22 0.0636(12) 0.0661(14) 0.0536(12) -0.0019(11) 0.0094(10) 0.0083(10) O1 0.0524(8) 0.0836(11) 0.0781(11) 0.0219(9) 0.0143(7) 0.0100(8) O2 0.0581(8) 0.0686(10) 0.0652(9) 0.0179(8) 0.0019(7) 0.0124(7) O3 0.0589(8) 0.0490(8) 0.0622(9) -0.0110(7) -0.0062(7) 0.0046(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 C1 O1 1.416(3) . ? C1 O2 1.416(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.363(3) . ? C2 O2 1.372(2) . ? C2 C7 1.373(3) . ? C3 C4 1.410(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.376(3) . ? C5 C8 1.512(3) . ? C6 C7 1.370(3) . ? C6 H6 0.9300 . ? C7 O1 1.372(2) . ? C8 O3 1.443(2) . ? C8 C9 1.505(3) . ? C8 H8 0.9800 . ? C9 C10 1.530(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.517(3) . ? C10 C17 1.522(2) . ? C10 H10 0.9800 . ? C11 C12 1.386(3) . ? C11 C16 1.394(3) . ? C12 C13 1.378(3) . ? C12 H12 0.9300 . ? C13 C14 1.363(4) . ? C13 H13 0.9300 . ? C14 C15 1.375(3) . ? C14 H14 0.9300 . ? C15 C16 1.387(3) . ? C15 H15 0.9300 . ? C16 O3 1.367(2) . ? C17 C18 1.376(3) . ? C17 C22 1.382(3) . ? C18 C19 1.377(3) . ? C18 H18 0.9300 . ? C19 C20 1.375(3) . ? C19 H19 0.9300 . ? C20 C21 1.363(4) . ? C20 H20 0.9300 . ? C21 C22 1.382(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 108.76(16) . . ? O1 C1 H1A 109.9 . . ? O2 C1 H1A 109.9 . . ? O1 C1 H1B 109.9 . . ? O2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C3 C2 O2 128.35(19) . . ? C3 C2 C7 121.95(18) . . ? O2 C2 C7 109.69(17) . . ? C2 C3 C4 115.8(2) . . ? C2 C3 H3 122.1 . . ? C4 C3 H3 122.1 . . ? C5 C4 C3 122.16(19) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C6 C5 C4 120.39(18) . . ? C6 C5 C8 118.81(19) . . ? C4 C5 C8 120.79(18) . . ? C7 C6 C5 117.46(19) . . ? C7 C6 H6 121.3 . . ? C5 C6 H6 121.3 . . ? C6 C7 O1 127.86(19) . . ? C6 C7 C2 122.24(18) . . ? O1 C7 C2 109.90(16) . . ? O3 C8 C9 110.30(15) . . ? O3 C8 C5 107.07(15) . . ? C9 C8 C5 114.20(17) . . ? O3 C8 H8 108.4 . . ? C9 C8 H8 108.4 . . ? C5 C8 H8 108.4 . . ? C8 C9 C10 109.78(16) . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C17 114.28(15) . . ? C11 C10 C9 108.74(15) . . ? C17 C10 C9 112.44(16) . . ? C11 C10 H10 107.0 . . ? C17 C10 H10 107.0 . . ? C9 C10 H10 107.0 . . ? C12 C11 C16 117.54(18) . . ? C12 C11 C10 122.03(18) . . ? C16 C11 C10 120.40(16) . . ? C13 C12 C11 121.7(2) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.5(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.7(2) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? O3 C16 C15 115.62(18) . . ? O3 C16 C11 123.62(16) . . ? C15 C16 C11 120.76(19) . . ? C18 C17 C22 118.07(19) . . ? C18 C17 C10 122.89(17) . . ? C22 C17 C10 119.04(18) . . ? C17 C18 C19 121.1(2) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C18 120.1(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.6(2) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.3(2) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 120.8(2) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C7 O1 C1 105.41(15) . . ? C2 O2 C1 105.48(15) . . ? C16 O3 C8 116.02(14) . . ? 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 O2 C2 C3 C4 179.8(2) . . . . ? C7 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C8 179.26(19) . . . . ? C4 C5 C6 C7 1.0(3) . . . . ? C8 C5 C6 C7 -178.20(18) . . . . ? C5 C6 C7 O1 179.75(19) . . . . ? C5 C6 C7 C2 -1.4(3) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? O2 C2 C7 C6 -178.83(18) . . . . ? C3 C2 C7 O1 179.68(19) . . . . ? O2 C2 C7 O1 0.2(2) . . . . ? C6 C5 C8 O3 -116.3(2) . . . . ? C4 C5 C8 O3 64.5(2) . . . . ? C6 C5 C8 C9 121.3(2) . . . . ? C4 C5 C8 C9 -57.9(3) . . . . ? O3 C8 C9 C10 63.9(2) . . . . ? C5 C8 C9 C10 -175.45(17) . . . . ? C8 C9 C10 C11 -49.8(2) . . . . ? C8 C9 C10 C17 -177.40(16) . . . . ? C17 C10 C11 C12 -34.1(3) . . . . ? C9 C10 C11 C12 -160.64(19) . . . . ? C17 C10 C11 C16 147.95(18) . . . . ? C9 C10 C11 C16 21.4(2) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? C10 C11 C12 C13 -177.2(2) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? C12 C13 C14 C15 -0.9(4) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C14 C15 C16 O3 -177.87(19) . . . . ? C14 C15 C16 C11 2.3(3) . . . . ? C12 C11 C16 O3 177.84(19) . . . . ? C10 C11 C16 O3 -4.1(3) . . . . ? C12 C11 C16 C15 -2.4(3) . . . . ? C10 C11 C16 C15 175.68(18) . . . . ? C11 C10 C17 C18 -69.3(2) . . . . ? C9 C10 C17 C18 55.3(2) . . . . ? C11 C10 C17 C22 111.5(2) . . . . ? C9 C10 C17 C22 -123.9(2) . . . . ? C22 C17 C18 C19 2.5(3) . . . . ? C10 C17 C18 C19 -176.69(19) . . . . ? C17 C18 C19 C20 -1.1(4) . . . . ? C18 C19 C20 C21 -1.1(4) . . . . ? C19 C20 C21 C22 1.7(4) . . . . ? C20 C21 C22 C17 -0.2(4) . . . . ? C18 C17 C22 C21 -1.9(3) . . . . ? C10 C17 C22 C21 177.35(19) . . . . ? C6 C7 O1 C1 -175.9(2) . . . . ? C2 C7 O1 C1 5.1(2) . . . . ? O2 C1 O1 C7 -8.6(2) . . . . ? C3 C2 O2 C1 175.1(2) . . . . ? C7 C2 O2 C1 -5.5(2) . . . . ? O1 C1 O2 C2 8.7(2) . . . . ? C15 C16 O3 C8 -163.46(17) . . . . ? C11 C16 O3 C8 16.4(3) . . . . ? C9 C8 O3 C16 -45.9(2) . . . . ? C5 C8 O3 C16 -170.71(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.332 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 932655' ####################################################################### # # 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_new2 #TrackingRef 'SJG-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 O5' _chemical_formula_weight 406.46 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 8.2985(3) _cell_length_b 28.7950(11) _cell_length_c 9.4916(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.617(2) _cell_angle_gamma 90.00 _cell_volume 2108.55(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5169 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.96 _exptl_crystal_description Rectangular _exptl_crystal_colour clear _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 17954 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.04 _reflns_number_total 6038 _reflns_number_gt 3535 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0503P)^2^+0.5203P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6038 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.38736(19) 0.14435(6) 0.49282(18) 0.0370(4) Uani 1 1 d . . . C2 C 0.2421(2) 0.13814(6) 0.3611(2) 0.0454(4) Uani 1 1 d . . . H2 H 0.2343 0.1534 0.2724 0.054 Uiso 1 1 calc R . . C3 C 0.1100(2) 0.10943(7) 0.3622(2) 0.0511(5) Uani 1 1 d . . . H3 H 0.0131 0.1051 0.2743 0.061 Uiso 1 1 calc R . . C4 C 0.1217(2) 0.08712(7) 0.4941(2) 0.0529(5) Uani 1 1 d . . . H4 H 0.0309 0.0686 0.4963 0.063 Uiso 1 1 calc R . . C5 C 0.2687(2) 0.09240(6) 0.6232(2) 0.0468(4) Uani 1 1 d . . . H5 H 0.2764 0.0767 0.7111 0.056 Uiso 1 1 calc R . . C6 C 0.4050(2) 0.12055(6) 0.62492(18) 0.0360(4) Uani 1 1 d . . . C7 C 0.5681(2) 0.12563(6) 0.76632(18) 0.0382(4) Uani 1 1 d . . . H7 H 0.5398 0.1469 0.8344 0.046 Uiso 1 1 calc R . . C8 C 0.7104(2) 0.14905(6) 0.7245(2) 0.0443(4) Uani 1 1 d . . . H8A H 0.8037 0.1591 0.8159 0.053 Uiso 1 1 calc R . . H8B H 0.7573 0.1270 0.6724 0.053 Uiso 1 1 calc R . . C9 C 0.6374(2) 0.19013(6) 0.6242(2) 0.0432(4) Uani 1 1 d . . . H9 H 0.5785 0.2100 0.6741 0.052 Uiso 1 1 calc R . . C10 C 0.62917(19) 0.08050(6) 0.85294(17) 0.0352(4) Uani 1 1 d . . . C11 C 0.6791(2) 0.04259(6) 0.78791(18) 0.0366(4) Uani 1 1 d . . . C12 C 0.7453(2) 0.00196(6) 0.86797(19) 0.0392(4) Uani 1 1 d . . . H12 H 0.7781 -0.0229 0.8218 0.047 Uiso 1 1 calc R . . C13 C 0.7609(2) -0.00049(6) 1.0175(2) 0.0405(4) Uani 1 1 d . . . C14 C 0.7098(2) 0.03600(6) 1.08622(19) 0.0409(4) Uani 1 1 d . . . H14 H 0.7194 0.0338 1.1868 0.049 Uiso 1 1 calc R . . C15 C 0.6441(2) 0.07590(6) 1.00366(18) 0.0367(4) Uani 1 1 d . . . C16 C 0.7253(3) 0.01249(7) 0.5710(2) 0.0574(5) Uani 1 1 d . . . H16A H 0.8473 0.0087 0.6261 0.086 Uiso 1 1 calc R . . H16B H 0.7055 0.0208 0.4681 0.086 Uiso 1 1 calc R . . H16C H 0.6664 -0.0161 0.5726 0.086 Uiso 1 1 calc R . . C17 C 0.8754(3) -0.07786(7) 1.0459(2) 0.0578(5) Uani 1 1 d . . . H17A H 0.7762 -0.0893 0.9637 0.087 Uiso 1 1 calc R . . H17B H 0.9174 -0.1015 1.1221 0.087 Uiso 1 1 calc R . . H17C H 0.9649 -0.0698 1.0088 0.087 Uiso 1 1 calc R . . C18 C 0.5981(3) 0.11092(8) 1.2152(2) 0.0544(5) Uani 1 1 d . . . H18A H 0.5292 0.0853 1.2252 0.082 Uiso 1 1 calc R . . H18B H 0.5543 0.1392 1.2408 0.082 Uiso 1 1 calc R . . H18C H 0.7162 0.1065 1.2822 0.082 Uiso 1 1 calc R . . C19 C 0.7675(2) 0.21935(6) 0.58886(19) 0.0409(4) Uani 1 1 d . . . C20 C 0.8888(3) 0.20004(6) 0.5370(2) 0.0520(5) Uani 1 1 d . . . H20 H 0.8881 0.1681 0.5218 0.062 Uiso 1 1 calc R . . C21 C 1.0105(2) 0.22706(7) 0.5075(2) 0.0499(5) Uani 1 1 d . . . H21 H 1.0903 0.2135 0.4724 0.060 Uiso 1 1 calc R . . C22 C 1.0120(2) 0.27439(6) 0.53085(19) 0.0424(4) Uani 1 1 d . . . C23 C 0.8918(2) 0.29393(6) 0.5819(2) 0.0486(4) Uani 1 1 d . . . H23 H 0.8921 0.3259 0.5970 0.058 Uiso 1 1 calc R . . C24 C 0.7723(2) 0.26679(6) 0.6107(2) 0.0458(4) Uani 1 1 d . . . H24 H 0.6927 0.2806 0.6456 0.055 Uiso 1 1 calc R . . C25 C 1.2458(3) 0.28740(9) 0.4473(3) 0.0796(7) Uani 1 1 d . . . H25A H 1.3213 0.2658 0.5181 0.119 Uiso 1 1 calc R . . H25B H 1.3129 0.3125 0.4311 0.119 Uiso 1 1 calc R . . H25C H 1.1856 0.2719 0.3529 0.119 Uiso 1 1 calc R . . O1 O 0.50979(14) 0.17465(4) 0.48113(13) 0.0450(3) Uani 1 1 d . . . O2 O 0.66086(17) 0.04816(4) 0.63961(13) 0.0487(3) Uani 1 1 d . . . O3 O 0.82801(17) -0.03801(4) 1.10949(15) 0.0561(4) Uani 1 1 d . . . O4 O 0.59015(17) 0.11342(4) 1.06387(14) 0.0512(3) Uani 1 1 d . . . O5 O 1.12483(17) 0.30493(5) 0.50582(16) 0.0581(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0351(7) 0.0390(9) 0.0374(9) 0.0033(7) 0.0141(7) 0.0046(7) C2 0.0395(8) 0.0547(11) 0.0388(10) 0.0068(8) 0.0107(7) 0.0061(8) C3 0.0354(8) 0.0568(12) 0.0546(12) -0.0002(9) 0.0090(8) 0.0023(8) C4 0.0397(9) 0.0487(11) 0.0721(14) 0.0031(10) 0.0226(9) -0.0012(8) C5 0.0497(9) 0.0447(11) 0.0514(11) 0.0092(8) 0.0251(9) 0.0060(8) C6 0.0402(8) 0.0332(9) 0.0364(9) 0.0019(7) 0.0162(7) 0.0074(6) C7 0.0514(9) 0.0334(9) 0.0294(8) 0.0020(7) 0.0143(7) 0.0048(7) C8 0.0453(9) 0.0415(10) 0.0368(9) 0.0025(7) 0.0042(7) -0.0052(7) C9 0.0474(9) 0.0412(10) 0.0384(10) 0.0001(7) 0.0130(8) -0.0003(7) C10 0.0393(8) 0.0355(9) 0.0294(8) 0.0033(7) 0.0112(6) -0.0011(6) C11 0.0410(8) 0.0375(9) 0.0305(8) 0.0018(7) 0.0122(7) -0.0025(7) C12 0.0420(8) 0.0342(9) 0.0415(10) 0.0023(7) 0.0156(7) 0.0012(7) C13 0.0375(8) 0.0403(10) 0.0419(10) 0.0117(8) 0.0124(7) -0.0012(7) C14 0.0440(8) 0.0485(11) 0.0312(9) 0.0082(7) 0.0151(7) -0.0015(7) C15 0.0389(8) 0.0398(9) 0.0325(9) -0.0001(7) 0.0145(7) -0.0023(7) C16 0.0753(13) 0.0571(13) 0.0462(11) -0.0039(9) 0.0299(10) 0.0080(10) C17 0.0539(11) 0.0442(11) 0.0702(14) 0.0137(10) 0.0170(10) 0.0078(9) C18 0.0557(10) 0.0751(14) 0.0370(10) -0.0034(9) 0.0226(9) 0.0041(10) C19 0.0436(8) 0.0422(10) 0.0338(9) 0.0021(7) 0.0105(7) -0.0007(7) C20 0.0649(11) 0.0338(10) 0.0598(13) -0.0057(9) 0.0260(10) -0.0039(8) C21 0.0533(10) 0.0471(11) 0.0548(12) -0.0054(9) 0.0262(9) -0.0005(8) C22 0.0424(8) 0.0436(10) 0.0358(9) 0.0000(7) 0.0082(7) -0.0049(7) C23 0.0563(10) 0.0360(10) 0.0523(12) -0.0017(8) 0.0187(9) -0.0006(8) C24 0.0473(9) 0.0409(10) 0.0488(11) -0.0007(8) 0.0173(8) 0.0044(8) C25 0.0637(13) 0.0862(18) 0.100(2) 0.0006(15) 0.0429(14) -0.0129(12) O1 0.0404(6) 0.0545(8) 0.0351(7) 0.0085(5) 0.0081(5) -0.0068(5) O2 0.0717(8) 0.0425(7) 0.0329(7) 0.0023(5) 0.0204(6) 0.0098(6) O3 0.0680(8) 0.0486(8) 0.0543(8) 0.0214(6) 0.0255(7) 0.0131(6) O4 0.0733(8) 0.0491(8) 0.0372(7) 0.0014(6) 0.0274(6) 0.0084(6) O5 0.0589(8) 0.0535(8) 0.0663(9) -0.0026(7) 0.0281(7) -0.0139(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 C1 O1 1.3743(19) . ? C1 C6 1.388(2) . ? C1 C2 1.392(2) . ? C2 C3 1.376(2) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 C7 1.522(2) . ? C7 C10 1.521(2) . ? C7 C8 1.533(2) . ? C7 H7 0.9800 . ? C8 C9 1.499(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O1 1.451(2) . ? C9 C19 1.501(2) . ? C9 H9 0.9800 . ? C10 C11 1.390(2) . ? C10 C15 1.396(2) . ? C11 O2 1.3685(19) . ? C11 C12 1.393(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C13 O3 1.3714(19) . ? C13 C14 1.383(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9300 . ? C15 O4 1.372(2) . ? C16 O2 1.421(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O3 1.418(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O4 1.415(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.380(2) . ? C19 C20 1.388(3) . ? C20 C21 1.383(3) . ? C20 H20 0.9300 . ? C21 C22 1.380(3) . ? C21 H21 0.9300 . ? C22 O5 1.368(2) . ? C22 C23 1.380(2) . ? C23 C24 1.366(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O5 1.408(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 123.44(14) . . ? O1 C1 C2 115.49(14) . . ? C6 C1 C2 121.06(15) . . ? C3 C2 C1 119.91(17) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.85(17) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.84(17) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 121.60(17) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 117.63(16) . . ? C5 C6 C7 121.53(15) . . ? C1 C6 C7 120.84(14) . . ? C10 C7 C6 113.92(13) . . ? C10 C7 C8 112.37(13) . . ? C6 C7 C8 109.47(13) . . ? C10 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? C8 C7 H7 106.9 . . ? C9 C8 C7 110.00(14) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O1 C9 C8 109.68(14) . . ? O1 C9 C19 107.48(13) . . ? C8 C9 C19 115.40(14) . . ? O1 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C19 C9 H9 108.0 . . ? C11 C10 C15 116.87(14) . . ? C11 C10 C7 121.68(14) . . ? C15 C10 C7 121.40(14) . . ? O2 C11 C10 115.24(14) . . ? O2 C11 C12 122.11(15) . . ? C10 C11 C12 122.64(15) . . ? C13 C12 C11 118.24(16) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? O3 C13 C12 123.88(16) . . ? O3 C13 C14 114.94(15) . . ? C12 C13 C14 121.17(15) . . ? C13 C14 C15 119.27(15) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? O4 C15 C14 122.59(14) . . ? O4 C15 C10 115.64(14) . . ? C14 C15 C10 121.78(15) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 117.72(16) . . ? C24 C19 C9 120.31(16) . . ? C20 C19 C9 121.96(16) . . ? C21 C20 C19 121.67(17) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C22 C21 C20 119.17(17) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? O5 C22 C23 115.39(16) . . ? O5 C22 C21 124.99(16) . . ? C23 C22 C21 119.61(16) . . ? C24 C23 C22 120.57(17) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 121.27(17) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 O1 C9 115.21(12) . . ? C11 O2 C16 117.94(13) . . ? C13 O3 C17 118.54(15) . . ? C15 O4 C18 118.83(14) . . ? C22 O5 C25 118.12(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.30(15) . . . . ? C6 C1 C2 C3 2.6(3) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -2.3(3) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? C4 C5 C6 C7 -178.87(16) . . . . ? O1 C1 C6 C5 177.49(15) . . . . ? C2 C1 C6 C5 -3.5(2) . . . . ? O1 C1 C6 C7 -2.1(2) . . . . ? C2 C1 C6 C7 176.92(15) . . . . ? C5 C6 C7 C10 40.0(2) . . . . ? C1 C6 C7 C10 -140.44(15) . . . . ? C5 C6 C7 C8 166.73(15) . . . . ? C1 C6 C7 C8 -13.7(2) . . . . ? C10 C7 C8 C9 173.38(14) . . . . ? C6 C7 C8 C9 45.75(18) . . . . ? C7 C8 C9 O1 -64.97(18) . . . . ? C7 C8 C9 C19 173.50(14) . . . . ? C6 C7 C10 C11 61.92(19) . . . . ? C8 C7 C10 C11 -63.31(19) . . . . ? C6 C7 C10 C15 -120.64(16) . . . . ? C8 C7 C10 C15 114.13(17) . . . . ? C15 C10 C11 O2 179.28(14) . . . . ? C7 C10 C11 O2 -3.2(2) . . . . ? C15 C10 C11 C12 -1.5(2) . . . . ? C7 C10 C11 C12 176.02(15) . . . . ? O2 C11 C12 C13 179.36(14) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C11 C12 C13 O3 -178.31(14) . . . . ? C11 C12 C13 C14 1.0(2) . . . . ? O3 C13 C14 C15 178.49(14) . . . . ? C12 C13 C14 C15 -0.9(2) . . . . ? C13 C14 C15 O4 179.74(14) . . . . ? C13 C14 C15 C10 -0.5(2) . . . . ? C11 C10 C15 O4 -178.56(14) . . . . ? C7 C10 C15 O4 3.9(2) . . . . ? C11 C10 C15 C14 1.7(2) . . . . ? C7 C10 C15 C14 -175.89(15) . . . . ? O1 C9 C19 C24 108.67(17) . . . . ? C8 C9 C19 C24 -128.62(18) . . . . ? O1 C9 C19 C20 -72.8(2) . . . . ? C8 C9 C19 C20 49.9(2) . . . . ? C24 C19 C20 C21 -0.2(3) . . . . ? C9 C19 C20 C21 -178.71(17) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? C20 C21 C22 O5 -179.84(17) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? O5 C22 C23 C24 179.93(16) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C22 C23 C24 C19 -0.3(3) . . . . ? C20 C19 C24 C23 0.2(3) . . . . ? C9 C19 C24 C23 178.75(16) . . . . ? C6 C1 O1 C9 -15.9(2) . . . . ? C2 C1 O1 C9 165.00(14) . . . . ? C8 C9 O1 C1 49.08(19) . . . . ? C19 C9 O1 C1 175.24(13) . . . . ? C10 C11 O2 C16 174.00(15) . . . . ? C12 C11 O2 C16 -5.2(2) . . . . ? C12 C13 O3 C17 -3.8(2) . . . . ? C14 C13 O3 C17 176.85(15) . . . . ? C14 C15 O4 C18 -1.5(2) . . . . ? C10 C15 O4 C18 178.73(15) . . . . ? C23 C22 O5 C25 -177.29(18) . . . . ? C21 C22 O5 C25 2.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.338 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 932656' ####################################################################### # # 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_new3 #TrackingRef 'SJG-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 O6' _chemical_formula_weight 510.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2911(6) _cell_length_b 19.7700(18) _cell_length_c 17.1314(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.314(3) _cell_angle_gamma 90.00 _cell_volume 2791.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1314 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 18.81 _exptl_crystal_description REctangular _exptl_crystal_colour clear _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 9049 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 18.86 _reflns_number_total 2192 _reflns_number_gt 1686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0676P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2192 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 C1 C 0.7624(4) 1.1633(2) 0.7573(2) 0.0626(11) Uani 1 1 d . . . H1 H 0.7286 1.1714 0.8065 0.075 Uiso 1 1 calc R . . C2 C 0.7510(5) 1.2130(2) 0.7015(4) 0.0815(13) Uani 1 1 d . . . H2 H 0.7096 1.2551 0.7129 0.098 Uiso 1 1 calc R . . C3 C 0.8003(5) 1.2013(2) 0.6285(3) 0.0873(13) Uani 1 1 d . . . H3 H 0.7928 1.2352 0.5906 0.105 Uiso 1 1 calc R . . C4 C 0.8604(4) 1.1387(2) 0.6125(2) 0.0666(11) Uani 1 1 d . . . H4 H 0.8929 1.1309 0.5630 0.080 Uiso 1 1 calc R . . C5 C 0.8748(4) 1.08699(18) 0.6671(2) 0.0440(9) Uani 1 1 d . . . C6 C 0.9378(3) 1.01910(16) 0.64680(18) 0.0398(9) Uani 1 1 d . . . H6 H 0.8831 1.0071 0.5950 0.048 Uiso 1 1 calc R . . C7 C 0.8854(3) 0.96583(15) 0.70571(17) 0.0376(9) Uani 1 1 d . . . H7 H 0.7676 0.9597 0.6954 0.045 Uiso 1 1 calc R . . C8 C 0.9234(4) 0.99209(17) 0.78941(18) 0.0434(9) Uani 1 1 d . . . H8 H 1.0391 1.0034 0.7975 0.052 Uiso 1 1 calc R . . C9 C 0.8246(4) 1.1006(2) 0.7400(2) 0.0469(9) Uani 1 1 d . . . C10 C 0.9655(4) 0.89782(17) 0.6954(2) 0.0415(9) Uani 1 1 d . . . C11 C 0.9036(4) 0.85342(17) 0.6297(2) 0.0422(9) Uani 1 1 d . . . C12 C 0.7722(5) 0.86724(18) 0.5768(2) 0.0623(11) Uani 1 1 d . . . H12 H 0.7110 0.9057 0.5841 0.075 Uiso 1 1 calc R . . C13 C 0.7266(5) 0.8259(2) 0.5124(2) 0.0692(11) Uani 1 1 d . . . H13 H 0.6374 0.8370 0.4769 0.083 Uiso 1 1 calc R . . C14 C 0.8148(5) 0.7690(2) 0.5022(2) 0.0598(10) Uani 1 1 d . . . C15 C 0.9441(5) 0.7528(2) 0.5551(3) 0.0764(12) Uani 1 1 d . . . H15 H 1.0017 0.7132 0.5491 0.092 Uiso 1 1 calc R . . C16 C 0.9891(4) 0.7951(2) 0.6172(2) 0.0646(11) Uani 1 1 d . . . H16 H 1.0798 0.7843 0.6518 0.077 Uiso 1 1 calc R . . C17 C 0.6585(6) 0.7405(2) 0.3808(3) 0.1094(17) Uani 1 1 d . . . H17A H 0.5597 0.7479 0.4040 0.164 Uiso 1 1 calc R . . H17B H 0.6440 0.7035 0.3443 0.164 Uiso 1 1 calc R . . H17C H 0.6860 0.7806 0.3536 0.164 Uiso 1 1 calc R . . C18 C 0.8870(4) 0.94606(16) 0.85486(19) 0.0417(9) Uani 1 1 d . . . C19 C 0.7362(4) 0.91603(18) 0.8577(2) 0.0456(9) Uani 1 1 d . . . C20 C 0.7015(4) 0.87773(18) 0.9210(2) 0.0521(10) Uani 1 1 d . . . H20 H 0.5998 0.8581 0.9219 0.063 Uiso 1 1 calc R . . C21 C 0.8209(5) 0.86918(18) 0.9828(2) 0.0573(10) Uani 1 1 d . . . C22 C 0.9726(4) 0.89719(18) 0.9828(2) 0.0544(10) Uani 1 1 d . . . H22 H 1.0519 0.8907 1.0249 0.065 Uiso 1 1 calc R . . C23 C 1.0040(4) 0.93510(17) 0.9189(2) 0.0446(9) Uani 1 1 d . . . C24 C 0.4697(4) 0.8950(2) 0.7901(2) 0.0811(13) Uani 1 1 d . . . H24A H 0.4842 0.8469 0.7941 0.122 Uiso 1 1 calc R . . H24B H 0.4080 0.9058 0.7410 0.122 Uiso 1 1 calc R . . H24C H 0.4128 0.9106 0.8325 0.122 Uiso 1 1 calc R . . C25 C 0.8944(6) 0.8187(3) 1.1092(3) 0.129(2) Uani 1 1 d . . . H25A H 0.9867 0.7963 1.0917 0.193 Uiso 1 1 calc R . . H25B H 0.8483 0.7906 1.1468 0.193 Uiso 1 1 calc R . . H25C H 0.9279 0.8610 1.1332 0.193 Uiso 1 1 calc R . . C26 C 1.2765(4) 0.95619(19) 0.9769(2) 0.0651(11) Uani 1 1 d . . . H26A H 1.2418 0.9738 1.0245 0.098 Uiso 1 1 calc R . . H26B H 1.3723 0.9797 0.9652 0.098 Uiso 1 1 calc R . . H26C H 1.3000 0.9088 0.9832 0.098 Uiso 1 1 calc R . . C27 C 1.1190(4) 1.02011(18) 0.6393(2) 0.0440(9) Uani 1 1 d . . . C28 C 1.2270(5) 1.06104(19) 0.6851(2) 0.0617(11) Uani 1 1 d . . . H28 H 1.1892 1.0887 0.7231 0.074 Uiso 1 1 calc R . . C29 C 1.3903(5) 1.0614(2) 0.6753(3) 0.0741(12) Uani 1 1 d . . . H29 H 1.4614 1.0889 0.7069 0.089 Uiso 1 1 calc R . . C30 C 1.4477(5) 1.0217(3) 0.6194(3) 0.0790(14) Uani 1 1 d . . . H30 H 1.5572 1.0228 0.6123 0.095 Uiso 1 1 calc R . . C31 C 1.3444(6) 0.9805(2) 0.5742(3) 0.0732(12) Uani 1 1 d . . . H31 H 1.3838 0.9529 0.5366 0.088 Uiso 1 1 calc R . . C32 C 1.1813(4) 0.97961(19) 0.5840(2) 0.0573(10) Uani 1 1 d . . . H32 H 1.1119 0.9512 0.5527 0.069 Uiso 1 1 calc R . . O1 O 0.8313(3) 1.05400(13) 0.79909(14) 0.0555(7) Uani 1 1 d . . . O2 O 1.0838(3) 0.88105(12) 0.74039(14) 0.0588(7) Uani 1 1 d . . . O3 O 0.7847(3) 0.72493(14) 0.44026(18) 0.0881(9) Uani 1 1 d . . . O4 O 0.6239(3) 0.92705(12) 0.79422(14) 0.0638(7) Uani 1 1 d . . . O5 O 0.7760(3) 0.83068(15) 1.04369(16) 0.0883(9) Uani 1 1 d . . . O6 O 1.1510(3) 0.96546(12) 0.91405(13) 0.0603(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.060(2) 0.053(3) 0.073(3) -0.011(3) -0.001(2) 0.004(2) C2 0.079(3) 0.049(3) 0.112(4) -0.013(3) -0.004(3) 0.018(2) C3 0.108(4) 0.056(4) 0.096(4) 0.016(3) 0.005(3) 0.011(3) C4 0.077(3) 0.050(3) 0.073(3) 0.005(3) 0.006(2) 0.007(2) C5 0.041(2) 0.038(3) 0.052(3) 0.005(2) 0.0004(18) -0.0004(17) C6 0.037(2) 0.042(2) 0.040(2) 0.0000(19) 0.0010(15) -0.0023(17) C7 0.0339(19) 0.039(2) 0.040(2) -0.0021(18) 0.0031(15) -0.0014(17) C8 0.039(2) 0.046(2) 0.045(3) -0.004(2) 0.0057(16) -0.0006(18) C9 0.040(2) 0.039(3) 0.060(3) -0.002(3) -0.0022(19) -0.0003(18) C10 0.039(2) 0.048(3) 0.038(2) 0.003(2) 0.0063(19) -0.003(2) C11 0.041(2) 0.040(3) 0.047(2) 0.000(2) 0.006(2) 0.0061(19) C12 0.069(3) 0.049(3) 0.064(3) -0.017(2) -0.012(2) 0.015(2) C13 0.073(3) 0.055(3) 0.074(3) -0.011(3) -0.019(2) 0.013(2) C14 0.075(3) 0.045(3) 0.059(3) -0.012(2) 0.004(2) -0.002(2) C15 0.077(3) 0.064(3) 0.087(3) -0.021(3) -0.002(3) 0.025(2) C16 0.058(2) 0.065(3) 0.068(3) -0.014(3) -0.004(2) 0.017(2) C17 0.154(4) 0.088(4) 0.074(3) -0.016(3) -0.044(3) 0.003(3) C18 0.040(2) 0.049(2) 0.036(2) -0.0019(19) 0.005(2) -0.0087(19) C19 0.045(3) 0.052(2) 0.039(3) -0.002(2) 0.002(2) -0.006(2) C20 0.045(2) 0.064(3) 0.047(3) -0.003(2) 0.002(2) -0.0175(18) C21 0.070(3) 0.057(3) 0.045(3) 0.005(2) 0.007(3) -0.020(2) C22 0.054(3) 0.067(3) 0.041(3) 0.003(2) -0.0015(19) -0.011(2) C23 0.042(3) 0.050(2) 0.041(3) -0.007(2) 0.004(2) -0.0088(19) C24 0.050(3) 0.115(4) 0.075(3) 0.011(3) -0.007(2) -0.027(2) C25 0.127(4) 0.180(6) 0.071(3) 0.050(3) -0.024(3) -0.064(4) C26 0.045(2) 0.085(3) 0.062(3) -0.013(2) -0.011(2) -0.007(2) C27 0.043(2) 0.049(2) 0.039(2) 0.012(2) 0.0038(19) 0.000(2) C28 0.051(3) 0.065(3) 0.069(3) 0.002(2) 0.005(2) -0.004(2) C29 0.047(3) 0.085(3) 0.089(4) 0.016(3) -0.002(2) -0.012(2) C30 0.045(3) 0.104(4) 0.090(4) 0.040(3) 0.015(3) 0.009(3) C31 0.060(3) 0.091(4) 0.074(3) 0.019(3) 0.027(3) 0.016(3) C32 0.053(3) 0.074(3) 0.047(3) 0.007(2) 0.0137(19) -0.001(2) O1 0.0655(16) 0.0482(18) 0.0547(17) -0.0067(15) 0.0152(12) 0.0022(13) O2 0.0544(15) 0.0649(18) 0.0537(16) 0.0027(13) -0.0084(13) 0.0126(13) O3 0.108(2) 0.068(2) 0.084(2) -0.0281(19) -0.0039(18) 0.0049(16) O4 0.0391(15) 0.093(2) 0.0575(17) 0.0172(14) -0.0042(13) -0.0179(13) O5 0.088(2) 0.113(2) 0.0591(18) 0.0302(18) -0.0100(16) -0.0446(17) O6 0.0440(16) 0.0842(19) 0.0509(16) 0.0004(13) -0.0024(13) -0.0199(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.367(5) . ? C1 C9 1.387(5) . ? C1 H1 0.9300 . ? C2 C3 1.378(6) . ? C2 H2 0.9300 . ? C3 C4 1.372(5) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C9 1.385(4) . ? C5 C6 1.495(4) . ? C6 C27 1.522(4) . ? C6 C7 1.553(4) . ? C6 H6 0.9800 . ? C7 C10 1.519(4) . ? C7 C8 1.525(4) . ? C7 H7 0.9800 . ? C8 O1 1.461(4) . ? C8 C18 1.500(4) . ? C8 H8 0.9800 . ? C9 O1 1.366(4) . ? C10 O2 1.224(3) . ? C10 C11 1.474(5) . ? C11 C12 1.366(4) . ? C11 C16 1.382(4) . ? C12 C13 1.391(5) . ? C12 H12 0.9300 . ? C13 C14 1.365(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 O3 1.374(4) . ? C15 C16 1.372(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O3 1.412(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.389(4) . ? C18 C23 1.400(4) . ? C19 O4 1.369(4) . ? C19 C20 1.378(4) . ? C20 C21 1.378(5) . ? C20 H20 0.9300 . ? C21 C22 1.375(5) . ? C21 O5 1.376(4) . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 O6 1.369(4) . ? C24 O4 1.421(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O5 1.427(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 O6 1.424(4) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C32 1.384(4) . ? C27 C28 1.385(5) . ? C28 C29 1.383(5) . ? C28 H28 0.9300 . ? C29 C30 1.362(5) . ? C29 H29 0.9300 . ? C30 C31 1.361(6) . ? C30 H30 0.9300 . ? C31 C32 1.381(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.4(4) . . ? C2 C1 H1 120.3 . . ? C9 C1 H1 120.3 . . ? C1 C2 C3 120.6(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 118.9(4) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 122.5(4) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C4 C5 C9 117.0(3) . . ? C4 C5 C6 120.8(3) . . ? C9 C5 C6 122.1(3) . . ? C5 C6 C27 112.4(3) . . ? C5 C6 C7 109.1(3) . . ? C27 C6 C7 114.4(2) . . ? C5 C6 H6 106.8 . . ? C27 C6 H6 106.8 . . ? C7 C6 H6 106.8 . . ? C10 C7 C8 111.2(3) . . ? C10 C7 C6 111.6(2) . . ? C8 C7 C6 109.6(2) . . ? C10 C7 H7 108.1 . . ? C8 C7 H7 108.1 . . ? C6 C7 H7 108.1 . . ? O1 C8 C18 105.8(2) . . ? O1 C8 C7 109.6(2) . . ? C18 C8 C7 117.3(3) . . ? O1 C8 H8 107.9 . . ? C18 C8 H8 107.9 . . ? C7 C8 H8 107.9 . . ? O1 C9 C5 123.0(3) . . ? O1 C9 C1 115.5(4) . . ? C5 C9 C1 121.5(4) . . ? O2 C10 C11 120.4(3) . . ? O2 C10 C7 119.8(3) . . ? C11 C10 C7 119.7(3) . . ? C12 C11 C16 116.7(3) . . ? C12 C11 C10 125.0(3) . . ? C16 C11 C10 118.3(3) . . ? C11 C12 C13 122.5(3) . . ? C11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C12 118.9(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 O3 115.3(4) . . ? C13 C14 O3 124.6(4) . . ? C14 C15 C16 120.0(4) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 121.9(4) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 117.1(3) . . ? C19 C18 C8 122.8(3) . . ? C23 C18 C8 120.0(3) . . ? O4 C19 C20 122.0(3) . . ? O4 C19 C18 116.1(3) . . ? C20 C19 C18 121.9(3) . . ? C21 C20 C19 118.5(3) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C22 C21 O5 123.1(4) . . ? C22 C21 C20 122.1(3) . . ? O5 C21 C20 114.8(3) . . ? C21 C22 C23 118.2(3) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? O6 C23 C22 122.4(3) . . ? O6 C23 C18 115.4(3) . . ? C22 C23 C18 122.2(3) . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O6 C26 H26A 109.5 . . ? O6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 117.4(3) . . ? C32 C27 C6 119.8(3) . . ? C28 C27 C6 122.9(3) . . ? C29 C28 C27 120.9(4) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C30 C29 C28 120.3(4) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C31 C30 C29 119.9(4) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 120.1(4) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 121.3(4) . . ? C31 C32 H32 119.3 . . ? C27 C32 H32 119.3 . . ? C9 O1 C8 117.4(3) . . ? C14 O3 C17 118.4(3) . . ? C19 O4 C24 119.8(3) . . ? C21 O5 C25 118.0(3) . . ? C23 O6 C26 118.6(3) . . ? 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 C1 C2 C3 0.2(6) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C2 C3 C4 C5 -0.5(6) . . . . ? C3 C4 C5 C9 0.3(5) . . . . ? C3 C4 C5 C6 178.7(3) . . . . ? C4 C5 C6 C27 71.6(4) . . . . ? C9 C5 C6 C27 -110.0(3) . . . . ? C4 C5 C6 C7 -160.4(3) . . . . ? C9 C5 C6 C7 18.0(4) . . . . ? C5 C6 C7 C10 -171.9(3) . . . . ? C27 C6 C7 C10 -45.0(4) . . . . ? C5 C6 C7 C8 -48.2(3) . . . . ? C27 C6 C7 C8 78.7(3) . . . . ? C10 C7 C8 O1 -174.3(2) . . . . ? C6 C7 C8 O1 61.8(3) . . . . ? C10 C7 C8 C18 -53.8(3) . . . . ? C6 C7 C8 C18 -177.6(3) . . . . ? C4 C5 C9 O1 179.7(3) . . . . ? C6 C5 C9 O1 1.2(5) . . . . ? C4 C5 C9 C1 0.2(5) . . . . ? C6 C5 C9 C1 -178.2(3) . . . . ? C2 C1 C9 O1 -179.9(3) . . . . ? C2 C1 C9 C5 -0.4(5) . . . . ? C8 C7 C10 O2 -22.3(4) . . . . ? C6 C7 C10 O2 100.5(3) . . . . ? C8 C7 C10 C11 159.8(3) . . . . ? C6 C7 C10 C11 -77.5(3) . . . . ? O2 C10 C11 C12 179.5(3) . . . . ? C7 C10 C11 C12 -2.5(5) . . . . ? O2 C10 C11 C16 -4.5(4) . . . . ? C7 C10 C11 C16 173.5(3) . . . . ? C16 C11 C12 C13 -1.1(5) . . . . ? C10 C11 C12 C13 175.0(3) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C12 C13 C14 O3 -178.4(3) . . . . ? C13 C14 C15 C16 -2.3(6) . . . . ? O3 C14 C15 C16 177.0(3) . . . . ? C14 C15 C16 C11 2.2(6) . . . . ? C12 C11 C16 C15 -0.5(5) . . . . ? C10 C11 C16 C15 -176.8(3) . . . . ? O1 C8 C18 C19 70.0(4) . . . . ? C7 C8 C18 C19 -52.5(4) . . . . ? O1 C8 C18 C23 -106.0(3) . . . . ? C7 C8 C18 C23 131.4(3) . . . . ? C23 C18 C19 O4 -179.6(3) . . . . ? C8 C18 C19 O4 4.3(4) . . . . ? C23 C18 C19 C20 0.8(5) . . . . ? C8 C18 C19 C20 -175.4(3) . . . . ? O4 C19 C20 C21 -179.8(3) . . . . ? C18 C19 C20 C21 -0.2(5) . . . . ? C19 C20 C21 C22 -0.5(5) . . . . ? C19 C20 C21 O5 179.6(3) . . . . ? O5 C21 C22 C23 -179.7(3) . . . . ? C20 C21 C22 C23 0.4(5) . . . . ? C21 C22 C23 O6 179.4(3) . . . . ? C21 C22 C23 C18 0.3(5) . . . . ? C19 C18 C23 O6 180.0(3) . . . . ? C8 C18 C23 O6 -3.8(4) . . . . ? C19 C18 C23 C22 -0.8(5) . . . . ? C8 C18 C23 C22 175.4(3) . . . . ? C5 C6 C27 C32 -144.8(3) . . . . ? C7 C6 C27 C32 90.0(3) . . . . ? C5 C6 C27 C28 34.2(4) . . . . ? C7 C6 C27 C28 -91.0(4) . . . . ? C32 C27 C28 C29 0.4(5) . . . . ? C6 C27 C28 C29 -178.6(3) . . . . ? C27 C28 C29 C30 0.6(6) . . . . ? C28 C29 C30 C31 -1.3(6) . . . . ? C29 C30 C31 C32 1.0(6) . . . . ? C30 C31 C32 C27 0.0(5) . . . . ? C28 C27 C32 C31 -0.7(5) . . . . ? C6 C27 C32 C31 178.4(3) . . . . ? C5 C9 O1 C8 11.8(4) . . . . ? C1 C9 O1 C8 -168.7(3) . . . . ? C18 C8 O1 C9 -170.6(3) . . . . ? C7 C8 O1 C9 -43.3(3) . . . . ? C15 C14 O3 C17 -176.4(4) . . . . ? C13 C14 O3 C17 2.9(6) . . . . ? C20 C19 O4 C24 -4.1(5) . . . . ? C18 C19 O4 C24 176.3(3) . . . . ? C22 C21 O5 C25 -1.0(6) . . . . ? C20 C21 O5 C25 178.9(4) . . . . ? C22 C23 O6 C26 1.3(4) . . . . ? C18 C23 O6 C26 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 18.86 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.190 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 932657' ####################################################################### # # 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_new4 #TrackingRef 'SJG-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O' _chemical_formula_weight 286.35 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.2722(19) _cell_length_b 5.7365(6) _cell_length_c 21.383(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.844(4) _cell_angle_gamma 90.00 _cell_volume 1580.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8164 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.85 _reflns_number_total 2662 _reflns_number_gt 1659 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0706P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2662 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.66374(16) 0.5973(4) -0.01090(9) 0.0490(5) Uani 1 1 d . . . H1 H 0.6333 0.4768 0.0114 0.059 Uiso 1 1 calc R . . C2 C 0.78062(15) 0.5785(4) 0.00950(9) 0.0515(6) Uani 1 1 d . . . H2A H 0.8112 0.6991 -0.0119 0.062 Uiso 1 1 calc R . . H2B H 0.8019 0.4286 -0.0039 0.062 Uiso 1 1 calc R . . C3 C 0.82073(15) 0.6033(3) 0.08213(9) 0.0449(5) Uani 1 1 d . . . H3 H 0.8036 0.4589 0.1018 0.054 Uiso 1 1 calc R . . C4 C 0.76431(15) 0.8003(3) 0.10667(9) 0.0435(5) Uani 1 1 d . . . C5 C 0.79973(16) 0.8909(4) 0.16806(9) 0.0537(6) Uani 1 1 d . . . H5 H 0.8591 0.8275 0.1949 0.064 Uiso 1 1 calc R . . C6 C 0.75022(18) 1.0712(4) 0.19074(10) 0.0607(6) Uani 1 1 d . . . H6 H 0.7765 1.1300 0.2319 0.073 Uiso 1 1 calc R . . C7 C 0.66095(17) 1.1640(4) 0.15164(10) 0.0574(6) Uani 1 1 d . . . H7 H 0.6265 1.2851 0.1666 0.069 Uiso 1 1 calc R . . C8 C 0.62328(16) 1.0776(4) 0.09076(10) 0.0517(6) Uani 1 1 d . . . H8 H 0.5633 1.1405 0.0645 0.062 Uiso 1 1 calc R . . C9 C 0.67419(15) 0.8966(4) 0.06810(9) 0.0434(5) Uani 1 1 d . . . C10 C 0.62239(15) 0.5689(4) -0.08206(9) 0.0459(5) Uani 1 1 d . . . C11 C 0.64066(16) 0.7348(4) -0.12447(10) 0.0540(6) Uani 1 1 d . . . H11 H 0.6755 0.8713 -0.1087 0.065 Uiso 1 1 calc R . . C12 C 0.60784(19) 0.7012(5) -0.19029(11) 0.0681(7) Uani 1 1 d . . . H12 H 0.6207 0.8145 -0.2185 0.082 Uiso 1 1 calc R . . C13 C 0.5564(2) 0.5007(6) -0.21390(12) 0.0775(8) Uani 1 1 d . . . H13 H 0.5353 0.4763 -0.2581 0.093 Uiso 1 1 calc R . . C14 C 0.5362(2) 0.3369(5) -0.17220(14) 0.0759(8) Uani 1 1 d . . . H14 H 0.5003 0.2020 -0.1882 0.091 Uiso 1 1 calc R . . C15 C 0.56859(18) 0.3696(4) -0.10648(12) 0.0623(6) Uani 1 1 d . . . H15 H 0.5541 0.2572 -0.0785 0.075 Uiso 1 1 calc R . . C16 C 0.93752(15) 0.6305(4) 0.10151(9) 0.0452(5) Uani 1 1 d . . . C17 C 0.99950(17) 0.4621(4) 0.13697(10) 0.0578(6) Uani 1 1 d . . . H17 H 0.9693 0.3284 0.1490 0.069 Uiso 1 1 calc R . . C18 C 1.10648(19) 0.4880(5) 0.15515(11) 0.0711(7) Uani 1 1 d . . . H18 H 1.1472 0.3725 0.1793 0.085 Uiso 1 1 calc R . . C19 C 1.15177(19) 0.6822(6) 0.13764(12) 0.0725(8) Uani 1 1 d . . . H19 H 1.2235 0.6995 0.1497 0.087 Uiso 1 1 calc R . . C20 C 1.09157(19) 0.8514(5) 0.10234(12) 0.0709(7) Uani 1 1 d . . . H20 H 1.1224 0.9843 0.0903 0.085 Uiso 1 1 calc R . . C21 C 0.98472(17) 0.8263(4) 0.08434(11) 0.0595(6) Uani 1 1 d . . . H21 H 0.9444 0.9429 0.0604 0.071 Uiso 1 1 calc R . . O1 O 0.63118(10) 0.8229(2) 0.00655(6) 0.0550(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0418(13) 0.0499(13) 0.0541(13) 0.0022(10) 0.0094(10) 0.0033(10) C2 0.0377(13) 0.0595(14) 0.0549(13) -0.0051(10) 0.0064(10) 0.0105(10) C3 0.0356(12) 0.0482(13) 0.0501(12) 0.0030(9) 0.0086(9) 0.0014(10) C4 0.0323(12) 0.0551(13) 0.0455(12) 0.0045(10) 0.0141(9) -0.0007(9) C5 0.0382(13) 0.0762(16) 0.0467(13) 0.0025(11) 0.0100(10) 0.0050(11) C6 0.0498(15) 0.0850(17) 0.0490(13) -0.0111(12) 0.0150(11) -0.0002(13) C7 0.0480(14) 0.0669(15) 0.0632(15) -0.0066(11) 0.0252(12) 0.0032(11) C8 0.0359(12) 0.0648(14) 0.0562(14) 0.0019(11) 0.0147(10) 0.0062(11) C9 0.0317(11) 0.0559(13) 0.0439(12) 0.0012(10) 0.0115(9) -0.0013(10) C10 0.0344(12) 0.0514(13) 0.0501(12) -0.0018(10) 0.0069(9) 0.0070(10) C11 0.0425(14) 0.0595(15) 0.0576(15) -0.0006(11) 0.0072(10) 0.0021(11) C12 0.0613(17) 0.088(2) 0.0554(16) 0.0089(13) 0.0148(12) 0.0217(15) C13 0.0612(17) 0.107(2) 0.0554(16) -0.0223(17) -0.0047(13) 0.0308(17) C14 0.0576(17) 0.0741(19) 0.084(2) -0.0264(16) -0.0066(14) 0.0061(13) C15 0.0482(14) 0.0593(15) 0.0751(17) -0.0073(12) 0.0066(12) -0.0022(12) C16 0.0366(12) 0.0551(13) 0.0442(12) -0.0041(10) 0.0101(9) 0.0069(10) C17 0.0446(14) 0.0633(15) 0.0634(14) 0.0025(11) 0.0088(11) 0.0121(12) C18 0.0486(16) 0.083(2) 0.0764(17) -0.0010(14) 0.0047(12) 0.0231(14) C19 0.0358(14) 0.104(2) 0.0780(17) -0.0210(15) 0.0143(12) 0.0099(15) C20 0.0482(16) 0.0817(18) 0.0882(18) -0.0087(14) 0.0268(13) -0.0107(14) C21 0.0444(14) 0.0645(15) 0.0704(15) 0.0067(11) 0.0152(11) 0.0030(11) O1 0.0423(9) 0.0703(10) 0.0483(9) -0.0076(7) 0.0025(7) 0.0164(7) _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 C1 O1 1.442(2) . ? C1 C10 1.498(3) . ? C1 C2 1.511(3) . ? C1 H1 0.9800 . ? C2 C3 1.523(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C16 1.514(3) . ? C3 C4 1.517(3) . ? C3 H3 0.9800 . ? C4 C5 1.385(3) . ? C4 C9 1.394(3) . ? C5 C6 1.374(3) . ? C5 H5 0.9300 . ? C6 C7 1.383(3) . ? C6 H6 0.9300 . ? C7 C8 1.371(3) . ? C7 H7 0.9300 . ? C8 C9 1.388(3) . ? C8 H8 0.9300 . ? C9 O1 1.370(2) . ? C10 C11 1.376(3) . ? C10 C15 1.382(3) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.371(4) . ? C12 H12 0.9300 . ? C13 C14 1.365(4) . ? C13 H13 0.9300 . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.373(3) . ? C16 C21 1.378(3) . ? C17 C18 1.387(3) . ? C17 H17 0.9300 . ? C18 C19 1.360(4) . ? C18 H18 0.9300 . ? C19 C20 1.365(4) . ? C19 H19 0.9300 . ? C20 C21 1.385(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C10 107.53(15) . . ? O1 C1 C2 109.88(16) . . ? C10 C1 C2 112.76(16) . . ? O1 C1 H1 108.9 . . ? C10 C1 H1 108.9 . . ? C2 C1 H1 108.9 . . ? C1 C2 C3 111.83(16) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C16 C3 C4 112.74(16) . . ? C16 C3 C2 111.96(15) . . ? C4 C3 C2 109.96(15) . . ? C16 C3 H3 107.3 . . ? C4 C3 H3 107.3 . . ? C2 C3 H3 107.3 . . ? C5 C4 C9 117.42(19) . . ? C5 C4 C3 121.57(18) . . ? C9 C4 C3 121.00(17) . . ? C6 C5 C4 122.3(2) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? O1 C9 C8 116.13(17) . . ? O1 C9 C4 123.18(18) . . ? C8 C9 C4 120.68(18) . . ? C11 C10 C15 118.7(2) . . ? C11 C10 C1 120.97(18) . . ? C15 C10 C1 120.30(19) . . ? C10 C11 C12 120.8(2) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C17 C16 C21 118.04(19) . . ? C17 C16 C3 121.18(19) . . ? C21 C16 C3 120.78(18) . . ? C16 C17 C18 121.1(2) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.7(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 120.3(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 120.7(2) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C9 O1 C1 116.35(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 61.2(2) . . . . ? C10 C1 C2 C3 -178.91(16) . . . . ? C1 C2 C3 C16 -169.18(17) . . . . ? C1 C2 C3 C4 -43.0(2) . . . . ? C16 C3 C4 C5 -40.9(3) . . . . ? C2 C3 C4 C5 -166.66(18) . . . . ? C16 C3 C4 C9 139.32(19) . . . . ? C2 C3 C4 C9 13.6(3) . . . . ? C9 C4 C5 C6 -1.0(3) . . . . ? C3 C4 C5 C6 179.21(19) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 O1 -179.57(18) . . . . ? C7 C8 C9 C4 -0.1(3) . . . . ? C5 C4 C9 O1 179.97(17) . . . . ? C3 C4 C9 O1 -0.3(3) . . . . ? C5 C4 C9 C8 0.6(3) . . . . ? C3 C4 C9 C8 -179.69(18) . . . . ? O1 C1 C10 C11 52.8(2) . . . . ? C2 C1 C10 C11 -68.5(2) . . . . ? O1 C1 C10 C15 -129.92(19) . . . . ? C2 C1 C10 C15 108.8(2) . . . . ? C15 C10 C11 C12 -1.4(3) . . . . ? C1 C10 C11 C12 175.98(18) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C11 C12 C13 C14 1.1(4) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C13 C14 C15 C10 -0.3(4) . . . . ? C11 C10 C15 C14 1.5(3) . . . . ? C1 C10 C15 C14 -175.9(2) . . . . ? C4 C3 C16 C17 121.6(2) . . . . ? C2 C3 C16 C17 -113.8(2) . . . . ? C4 C3 C16 C21 -58.0(2) . . . . ? C2 C3 C16 C21 66.6(2) . . . . ? C21 C16 C17 C18 0.1(3) . . . . ? C3 C16 C17 C18 -179.47(19) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C20 0.2(4) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C17 C16 C21 C20 0.1(3) . . . . ? C3 C16 C21 C20 179.72(19) . . . . ? C19 C20 C21 C16 -0.2(3) . . . . ? C8 C9 O1 C1 -162.60(17) . . . . ? C4 C9 O1 C1 18.0(3) . . . . ? C10 C1 O1 C9 -170.57(15) . . . . ? C2 C1 O1 C9 -47.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 24.85 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.181 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 932658' ####################################################################### # # 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_new5 #TrackingRef 'SJG-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 I O6' _chemical_formula_weight 519.29 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3330(4) _cell_length_b 9.5986(4) _cell_length_c 14.6529(7) _cell_angle_alpha 107.576(2) _cell_angle_beta 92.267(2) _cell_angle_gamma 90.024(2) _cell_volume 1250.30(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5149 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.19 _exptl_crystal_description Block _exptl_crystal_colour clear _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 518 _exptl_absorpt_coefficient_mu 1.312 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 15676 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.58 _reflns_number_total 5737 _reflns_number_gt 4851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.2000P)^2^+0.0010P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.001(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5737 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.2301 _refine_ls_wR_factor_gt 0.1982 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.5967(11) 0.1866(11) 0.5225(6) 0.068(3) Uani 0.608(12) 1 d P A 1 C2 C 0.681(5) 0.073(2) 0.518(2) 0.27(3) Uani 0.608(12) 1 d P A 1 H2 H 0.6720 -0.0123 0.4667 0.327 Uiso 0.608(12) 1 calc PR A 1 C6 C 0.592(2) 0.295(3) 0.6038(11) 0.115(7) Uani 0.608(12) 1 d P A 1 H6 H 0.5441 0.3809 0.6057 0.138 Uiso 0.608(12) 1 calc PR A 1 C7 C 0.5015(11) 0.1856(12) 0.4340(6) 0.071(3) Uani 0.608(12) 1 d P A 1 H7A H 0.4851 0.0861 0.3931 0.086 Uiso 0.608(12) 1 calc PR A 1 H7B H 0.4095 0.2290 0.4536 0.086 Uiso 0.608(12) 1 calc PR A 1 C1X C 0.6965(14) 0.2601(17) 0.5262(9) 0.062(4) Uani 0.393(12) 1 d P A 2 C2X C 0.749(3) 0.126(3) 0.5192(12) 0.100(8) Uani 0.393(12) 1 d P A 2 H2X H 0.7570 0.0586 0.4588 0.121 Uiso 0.393(12) 1 calc PR A 2 C6X C 0.650(3) 0.344(4) 0.611(2) 0.091(7) Uani 0.393(12) 1 d P A 2 H6X H 0.6139 0.4375 0.6202 0.109 Uiso 0.393(12) 1 calc PR A 2 C7X C 0.6735(18) 0.3065(18) 0.4358(11) 0.069(4) Uani 0.393(12) 1 d P A 2 H7X1 H 0.6723 0.4124 0.4551 0.083 Uiso 0.393(12) 1 calc PR A 2 H7X2 H 0.7564 0.2760 0.3971 0.083 Uiso 0.393(12) 1 calc PR A 2 C3 C 0.7911(16) 0.0860(13) 0.5998(10) 0.145(5) Uani 1 1 d . . . H3 H 0.8795 0.0401 0.5935 0.174 Uiso 1 1 calc R A 1 C4 C 0.7407(12) 0.1763(12) 0.6850(6) 0.109(3) Uani 1 1 d . A . H4 H 0.7681 0.1594 0.7424 0.131 Uiso 1 1 calc R . . C5 C 0.6599(12) 0.2787(14) 0.6861(5) 0.120(4) Uani 1 1 d . . . H5 H 0.6437 0.3479 0.7446 0.144 Uiso 1 1 calc R A 1 C8 C 0.5140(5) 0.2831(5) 0.3041(3) 0.0528(10) Uani 1 1 d . A . C9 C 0.5977(4) 0.3579(5) 0.2580(3) 0.0466(8) Uani 1 1 d . . . H9 H 0.6872 0.3945 0.2845 0.056 Uiso 1 1 calc R . . C10 C 0.5488(3) 0.3787(5) 0.1722(3) 0.0399(8) Uani 1 1 d . . . C11 C 0.4136(3) 0.3275(4) 0.1319(3) 0.0341(6) Uani 1 1 d . . . C12 C 0.3318(4) 0.2540(5) 0.1803(3) 0.0470(9) Uani 1 1 d . . . H12 H 0.2405 0.2208 0.1554 0.056 Uiso 1 1 calc R . . C13 C 0.3805(5) 0.2280(6) 0.2644(4) 0.0588(12) Uani 1 1 d . . . H13 H 0.3248 0.1746 0.2935 0.071 Uiso 1 1 calc R . . C14 C 0.3613(3) 0.3542(4) 0.0394(3) 0.0359(7) Uani 1 1 d . . . H14 H 0.4304 0.3082 -0.0090 0.043 Uiso 1 1 calc R . . C15 C 0.2151(3) 0.2851(4) 0.0011(2) 0.0344(7) Uani 1 1 d . . . C16 C 0.2037(3) 0.1608(4) -0.0775(3) 0.0344(7) Uani 1 1 d . . . C17 C 0.0714(4) 0.0914(4) -0.1105(3) 0.0389(7) Uani 1 1 d . . . C18 C -0.0512(3) 0.1489(4) -0.0625(3) 0.0383(7) Uani 1 1 d . . . C19 C -0.0438(3) 0.2745(4) 0.0139(3) 0.0383(7) Uani 1 1 d . . . C20 C 0.0887(3) 0.3439(4) 0.0460(2) 0.0352(7) Uani 1 1 d . . . C21 C 0.3653(6) 0.1430(7) -0.2005(4) 0.0709(14) Uani 1 1 d . . . H21A H 0.2982 0.1020 -0.2532 0.106 Uiso 1 1 calc R . . H21B H 0.4601 0.1100 -0.2189 0.106 Uiso 1 1 calc R . . H21C H 0.3632 0.2477 -0.1833 0.106 Uiso 1 1 calc R . . C22 C -0.3009(4) 0.1163(5) -0.0419(4) 0.0533(11) Uani 1 1 d . . . H22A H -0.2840 0.1087 0.0214 0.080 Uiso 1 1 calc R . . H22B H -0.3803 0.0541 -0.0730 0.080 Uiso 1 1 calc R . . H22C H -0.3225 0.2157 -0.0380 0.080 Uiso 1 1 calc R . . C23 C -0.0139(5) 0.5272(6) 0.1735(4) 0.0594(12) Uani 1 1 d . . . H23A H -0.0793 0.5639 0.1343 0.089 Uiso 1 1 calc R . . H23B H 0.0163 0.6055 0.2292 0.089 Uiso 1 1 calc R . . H23C H -0.0609 0.4525 0.1930 0.089 Uiso 1 1 calc R . . I1 I 0.05694(3) -0.09799(3) -0.226385(19) 0.0567(2) Uani 1 1 d . . . O1 O 0.5713(6) 0.2636(6) 0.3869(3) 0.0836(14) Uani 1 1 d . . . O2 O 0.6412(3) 0.4498(4) 0.1310(2) 0.0519(8) Uani 1 1 d . . . O3 O 0.3631(3) 0.5082(3) 0.0487(2) 0.0426(6) Uani 1 1 d . . . O4 O 0.3274(3) 0.0971(4) -0.1203(2) 0.0475(7) Uani 1 1 d . . . O5 O -0.1757(3) 0.0725(3) -0.0960(2) 0.0514(7) Uani 1 1 d . . . O6 O 0.1070(3) 0.4679(3) 0.1206(2) 0.0450(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.086(6) 0.085(6) 0.037(4) 0.028(4) -0.009(3) -0.016(5) C2 0.52(7) 0.087(12) 0.21(3) 0.080(16) -0.27(4) -0.12(3) C6 0.112(15) 0.149(19) 0.050(6) -0.018(9) -0.015(8) 0.034(11) C7 0.089(6) 0.094(7) 0.043(4) 0.039(4) -0.008(4) -0.012(5) C1X 0.060(7) 0.082(10) 0.045(6) 0.021(6) 0.005(5) 0.005(6) C2X 0.142(18) 0.117(18) 0.040(8) 0.019(9) 0.011(9) 0.070(16) C6X 0.074(14) 0.096(16) 0.098(19) 0.019(13) 0.021(12) -0.003(10) C7X 0.081(9) 0.066(9) 0.057(8) 0.018(7) -0.021(6) 0.007(7) C3 0.191(12) 0.121(8) 0.131(10) 0.056(8) -0.035(9) 0.042(8) C4 0.149(8) 0.125(7) 0.062(4) 0.046(5) -0.042(5) -0.050(6) C5 0.139(8) 0.160(10) 0.041(3) 0.002(4) -0.002(4) 0.029(7) C8 0.061(2) 0.059(3) 0.043(2) 0.024(2) -0.0070(17) -0.0015(19) C9 0.0380(17) 0.053(2) 0.049(2) 0.0160(18) -0.0118(14) -0.0005(15) C10 0.0291(14) 0.051(2) 0.0418(19) 0.0176(17) 0.0015(12) 0.0016(13) C11 0.0301(13) 0.0314(16) 0.0398(17) 0.0099(13) -0.0037(11) 0.0009(11) C12 0.0356(16) 0.056(2) 0.055(2) 0.0259(19) -0.0061(14) -0.0123(14) C13 0.055(2) 0.077(3) 0.057(3) 0.039(3) -0.0041(18) -0.010(2) C14 0.0250(12) 0.046(2) 0.0371(17) 0.0137(15) -0.0001(11) -0.0014(11) C15 0.0256(13) 0.0428(19) 0.0354(16) 0.0132(14) -0.0024(11) -0.0017(11) C16 0.0312(13) 0.0392(19) 0.0331(16) 0.0115(14) 0.0012(11) 0.0041(12) C17 0.0402(16) 0.041(2) 0.0345(17) 0.0096(15) -0.0037(13) 0.0007(14) C18 0.0296(14) 0.047(2) 0.0400(18) 0.0163(16) -0.0070(12) -0.0049(12) C19 0.0265(13) 0.048(2) 0.0398(18) 0.0120(16) -0.0001(11) 0.0055(12) C20 0.0313(14) 0.0393(19) 0.0332(16) 0.0086(14) -0.0014(11) 0.0003(12) C21 0.072(3) 0.082(4) 0.055(3) 0.011(3) 0.024(2) -0.003(3) C22 0.0291(16) 0.050(2) 0.074(3) 0.010(2) -0.0018(16) -0.0059(14) C23 0.041(2) 0.065(3) 0.058(3) -0.004(2) 0.0121(17) 0.0022(17) I1 0.0567(3) 0.0530(3) 0.0497(3) 0.00024(17) -0.00233(15) 0.00025(16) O1 0.097(3) 0.104(4) 0.062(2) 0.046(3) -0.023(2) -0.001(3) O2 0.0323(12) 0.072(2) 0.0564(18) 0.0288(16) -0.0067(11) -0.0133(12) O3 0.0374(12) 0.0463(15) 0.0495(15) 0.0224(13) 0.0017(10) -0.0043(10) O4 0.0330(12) 0.0573(18) 0.0498(16) 0.0120(14) 0.0069(10) 0.0084(11) O5 0.0330(12) 0.0545(18) 0.0592(18) 0.0070(14) -0.0040(11) -0.0090(11) O6 0.0306(11) 0.0490(16) 0.0466(15) 0.0012(12) 0.0026(10) -0.0018(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 C1 C6 1.327(19) . ? C1 C2 1.33(4) . ? C1 C7 1.540(11) . ? C2 C3 1.52(2) . ? C2 H2 0.9300 . ? C6 C5 1.39(2) . ? C6 H6 0.9300 . ? C7 O1 1.345(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C1X C6X 1.35(3) . ? C1X C2X 1.35(3) . ? C1X C7X 1.526(18) . ? C2X C3 1.39(2) . ? C2X H2X 0.9300 . ? C6X C5 1.42(3) . ? C6X H6X 0.9300 . ? C7X O1 1.167(15) . ? C7X H7X1 0.9700 . ? C7X H7X2 0.9700 . ? C3 C4 1.387(17) . ? C3 H3 0.9300 . ? C4 C5 1.236(15) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C8 O1 1.371(5) . ? C8 C9 1.384(6) . ? C8 C13 1.388(6) . ? C9 C10 1.390(5) . ? C9 H9 0.9300 . ? C10 O2 1.365(4) . ? C10 C11 1.396(5) . ? C11 C12 1.389(5) . ? C11 C14 1.516(5) . ? C12 C13 1.388(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O3 1.443(5) . ? C14 C15 1.526(4) . ? C14 H14 0.9800 . ? C15 C16 1.387(5) . ? C15 C20 1.407(4) . ? C16 O4 1.388(4) . ? C16 C17 1.400(5) . ? C17 C18 1.392(5) . ? C17 I1 2.080(4) . ? C18 O5 1.366(4) . ? C18 C19 1.375(6) . ? C19 C20 1.399(4) . ? C20 O6 1.357(5) . ? C21 O4 1.430(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O5 1.430(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O6 1.415(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C6 C1 C2 119.7(15) . . ? C6 C1 C7 121.3(13) . . ? C2 C1 C7 118.9(12) . . ? C1 C2 C3 118.1(18) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C1 C6 C5 118.9(19) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? O1 C7 C1 107.2(7) . . ? O1 C7 H7A 110.3 . . ? C1 C7 H7A 110.3 . . ? O1 C7 H7B 110.3 . . ? C1 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? C6X C1X C2X 119.2(19) . . ? C6X C1X C7X 120.8(19) . . ? C2X C1X C7X 119.5(13) . . ? C1X C2X C3 121.8(17) . . ? C1X C2X H2X 119.1 . . ? C3 C2X H2X 119.1 . . ? C1X C6X C5 115(3) . . ? C1X C6X H6X 122.6 . . ? C5 C6X H6X 122.6 . . ? O1 C7X C1X 118.4(14) . . ? O1 C7X H7X1 107.7 . . ? C1X C7X H7X1 107.7 . . ? O1 C7X H7X2 107.7 . . ? C1X C7X H7X2 107.7 . . ? H7X1 C7X H7X2 107.1 . . ? C4 C3 C2X 114.3(11) . . ? C4 C3 C2 110(2) . . ? C2X C3 C2 32.0(17) . . ? C4 C3 H3 124.9 . . ? C2X C3 H3 112.4 . . ? C2 C3 H3 124.9 . . ? C5 C4 C3 121.3(7) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 123.0(12) . . ? C4 C5 C6X 123.3(15) . . ? C6 C5 C6X 28.8(11) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C6X C5 H5 110.1 . . ? O1 C8 C9 117.0(4) . . ? O1 C8 C13 123.1(4) . . ? C9 C8 C13 119.8(4) . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? O2 C10 C9 115.9(3) . . ? O2 C10 C11 123.2(3) . . ? C9 C10 C11 120.9(3) . . ? C12 C11 C10 117.2(3) . . ? C12 C11 C14 122.8(3) . . ? C10 C11 C14 120.0(3) . . ? C13 C12 C11 122.8(4) . . ? C13 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? C8 C13 C12 118.8(4) . . ? C8 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? O3 C14 C11 111.0(3) . . ? O3 C14 C15 111.1(3) . . ? C11 C14 C15 114.1(3) . . ? O3 C14 H14 106.7 . . ? C11 C14 H14 106.7 . . ? C15 C14 H14 106.7 . . ? C16 C15 C20 118.3(3) . . ? C16 C15 C14 120.8(3) . . ? C20 C15 C14 120.9(3) . . ? C15 C16 O4 119.3(3) . . ? C15 C16 C17 121.6(3) . . ? O4 C16 C17 118.9(3) . . ? C18 C17 C16 118.9(3) . . ? C18 C17 I1 120.0(3) . . ? C16 C17 I1 121.1(3) . . ? O5 C18 C19 123.4(3) . . ? O5 C18 C17 115.8(3) . . ? C19 C18 C17 120.8(3) . . ? C18 C19 C20 120.0(3) . . ? O6 C20 C19 124.4(3) . . ? O6 C20 C15 115.2(3) . . ? C19 C20 C15 120.4(3) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O5 C22 H22A 109.5 . . ? O5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O6 C23 H23A 109.5 . . ? O6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7X O1 C7 103.4(9) . . ? C7X O1 C8 135.0(9) . . ? C7 O1 C8 121.4(6) . . ? C16 O4 C21 113.9(3) . . ? C18 O5 C22 117.8(3) . . ? C20 O6 C23 118.3(3) . . ? 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 C1 C2 C3 -13(4) . . . . ? C7 C1 C2 C3 170(2) . . . . ? C2 C1 C6 C5 -9(3) . . . . ? C7 C1 C6 C5 168.5(15) . . . . ? C6 C1 C7 O1 85.3(17) . . . . ? C2 C1 C7 O1 -98(2) . . . . ? C6X C1X C2X C3 -17(4) . . . . ? C7X C1X C2X C3 171(2) . . . . ? C2X C1X C6X C5 -1(3) . . . . ? C7X C1X C6X C5 171.5(15) . . . . ? C6X C1X C7X O1 -93(2) . . . . ? C2X C1X C7X O1 79(2) . . . . ? C1X C2X C3 C4 16(4) . . . . ? C1X C2X C3 C2 106(4) . . . . ? C1 C2 C3 C4 31(4) . . . . ? C1 C2 C3 C2X -73(2) . . . . ? C2X C3 C4 C5 3(2) . . . . ? C2 C3 C4 C5 -31.2(19) . . . . ? C3 C4 C5 C6 13(2) . . . . ? C3 C4 C5 C6X -22(2) . . . . ? C1 C6 C5 C4 10(3) . . . . ? C1 C6 C5 C6X 110(5) . . . . ? C1X C6X C5 C4 21(3) . . . . ? C1X C6X C5 C6 -78(4) . . . . ? O1 C8 C9 C10 178.3(5) . . . . ? C13 C8 C9 C10 0.3(7) . . . . ? C8 C9 C10 O2 -178.0(4) . . . . ? C8 C9 C10 C11 1.3(7) . . . . ? O2 C10 C11 C12 178.5(4) . . . . ? C9 C10 C11 C12 -0.7(6) . . . . ? O2 C10 C11 C14 -2.0(6) . . . . ? C9 C10 C11 C14 178.8(4) . . . . ? C10 C11 C12 C13 -1.4(7) . . . . ? C14 C11 C12 C13 179.1(4) . . . . ? O1 C8 C13 C12 179.8(5) . . . . ? C9 C8 C13 C12 -2.3(8) . . . . ? C11 C12 C13 C8 2.9(8) . . . . ? C12 C11 C14 O3 122.8(4) . . . . ? C10 C11 C14 O3 -56.6(4) . . . . ? C12 C11 C14 C15 -3.6(5) . . . . ? C10 C11 C14 C15 177.0(3) . . . . ? O3 C14 C15 C16 128.1(3) . . . . ? C11 C14 C15 C16 -105.5(4) . . . . ? O3 C14 C15 C20 -53.3(4) . . . . ? C11 C14 C15 C20 73.0(4) . . . . ? C20 C15 C16 O4 -177.1(3) . . . . ? C14 C15 C16 O4 1.4(5) . . . . ? C20 C15 C16 C17 -2.1(5) . . . . ? C14 C15 C16 C17 176.5(3) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? O4 C16 C17 C18 174.8(3) . . . . ? C15 C16 C17 I1 -178.4(3) . . . . ? O4 C16 C17 I1 -3.3(4) . . . . ? C16 C17 C18 O5 -177.4(3) . . . . ? I1 C17 C18 O5 0.7(4) . . . . ? C16 C17 C18 C19 2.3(5) . . . . ? I1 C17 C18 C19 -179.6(3) . . . . ? O5 C18 C19 C20 177.9(3) . . . . ? C17 C18 C19 C20 -1.8(5) . . . . ? C18 C19 C20 O6 -179.9(3) . . . . ? C18 C19 C20 C15 -0.7(5) . . . . ? C16 C15 C20 O6 -178.2(3) . . . . ? C14 C15 C20 O6 3.3(5) . . . . ? C16 C15 C20 C19 2.6(5) . . . . ? C14 C15 C20 C19 -176.0(3) . . . . ? C1X C7X O1 C7 2.3(16) . . . . ? C1X C7X O1 C8 178.3(9) . . . . ? C1 C7 O1 C7X -3.4(13) . . . . ? C1 C7 O1 C8 179.9(7) . . . . ? C9 C8 O1 C7X 8.2(15) . . . . ? C13 C8 O1 C7X -173.9(13) . . . . ? C9 C8 O1 C7 -176.3(7) . . . . ? C13 C8 O1 C7 1.6(10) . . . . ? C15 C16 O4 C21 -95.0(4) . . . . ? C17 C16 O4 C21 89.8(5) . . . . ? C19 C18 O5 C22 -7.4(6) . . . . ? C17 C18 O5 C22 172.3(4) . . . . ? C19 C20 O6 C23 3.8(6) . . . . ? C15 C20 O6 C23 -175.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 2.812 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.202 _database_code_depnum_ccdc_archive 'CCDC 932659'