# 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H28 O6' _chemical_formula_sum 'C34 H28 O6' _chemical_formula_weight 532.56 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.2731(8) _cell_length_b 10.6669(7) _cell_length_c 22.7178(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.852(2) _cell_angle_gamma 90.00 _cell_volume 2730.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4511 _cell_measurement_theta_min 2.506 _cell_measurement_theta_max 22.862 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.088 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30839 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4848 _reflns_number_gt 3334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics various _computing_publication_material 'SHELXTL Version 6.14 (Bruker, 2000)' _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^)+(0.0336P)^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_number_reflns 4848 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0755 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.78590(17) -0.15367(17) 0.36729(8) 0.0353(4) Uani 1 1 d . . . C2 C 0.72562(16) -0.23365(18) 0.27471(8) 0.0431(5) Uani 1 1 d . . . H2A H 0.7528 -0.3184 0.2868 0.052 Uiso 1 1 calc R . . H2B H 0.7893 -0.1931 0.2525 0.052 Uiso 1 1 calc R . . C3 C 0.61439(16) -0.24260(17) 0.23711(7) 0.0348(4) Uani 1 1 d . . . C4 C 0.58861(17) -0.35083(18) 0.20584(8) 0.0403(5) Uani 1 1 d . . . H4 H 0.6401 -0.4211 0.2097 0.048 Uiso 1 1 calc R . . C5 C 0.48847(17) -0.35802(18) 0.16896(8) 0.0404(5) Uani 1 1 d . . . H5 H 0.4732 -0.4328 0.1473 0.048 Uiso 1 1 calc R . . C6 C 0.41013(16) -0.25817(17) 0.16306(7) 0.0344(4) Uani 1 1 d . . . C7 C 0.43661(16) -0.14957(17) 0.19485(7) 0.0359(4) Uani 1 1 d . . . H7 H 0.3846 -0.0797 0.1916 0.043 Uiso 1 1 calc R . . C8 C 0.53728(16) -0.14184(17) 0.23099(8) 0.0372(5) Uani 1 1 d . . . H8 H 0.5539 -0.0665 0.2519 0.045 Uiso 1 1 calc R . . C9 C 0.30717(17) -0.26565(17) 0.12141(8) 0.0406(5) Uani 1 1 d . . . H9 H 0.3193 -0.3118 0.0864 0.049 Uiso 1 1 calc R . . C10 C 0.19998(17) -0.21643(18) 0.12647(8) 0.0413(5) Uani 1 1 d . . . H10 H 0.1476 -0.2227 0.0930 0.050 Uiso 1 1 calc R . . C11 C 0.15322(15) -0.15272(17) 0.17872(8) 0.0343(4) Uani 1 1 d . . . C12 C 0.09132(15) -0.04058(18) 0.17380(8) 0.0379(5) Uani 1 1 d . . . H12 H 0.0749 -0.0060 0.1359 0.046 Uiso 1 1 calc R . . C13 C 0.05314(15) 0.02159(18) 0.22302(8) 0.0379(5) Uani 1 1 d . . . H13 H 0.0114 0.0986 0.2186 0.046 Uiso 1 1 calc R . . C14 C 0.07507(15) -0.02722(17) 0.27893(8) 0.0327(4) Uani 1 1 d . . . C15 C 0.13128(16) -0.14215(18) 0.28379(8) 0.0381(5) Uani 1 1 d . . . H15 H 0.1438 -0.1789 0.3216 0.046 Uiso 1 1 calc R . . C16 C 0.16946(16) -0.20429(18) 0.23464(8) 0.0400(5) Uani 1 1 d . . . H16 H 0.2074 -0.2834 0.2390 0.048 Uiso 1 1 calc R . . C17 C 0.04614(15) 0.04578(17) 0.33290(8) 0.0376(5) Uani 1 1 d . . . H17A H -0.0384 0.0710 0.3316 0.045 Uiso 1 1 calc R . . H17B H 0.0622 -0.0048 0.3688 0.045 Uiso 1 1 calc R . . C18 C 0.12029(15) 0.22939(18) 0.37951(8) 0.0343(4) Uani 1 1 d . . . C19 C 0.19301(17) 0.42414(18) 0.41379(8) 0.0450(5) Uani 1 1 d . . . H19A H 0.1122 0.4345 0.4290 0.054 Uiso 1 1 calc R . . H19B H 0.2159 0.5045 0.3956 0.054 Uiso 1 1 calc R . . C20 C 0.27749(16) 0.39669(16) 0.46450(8) 0.0359(4) Uani 1 1 d . . . C21 C 0.39196(16) 0.35520(16) 0.45569(8) 0.0376(5) Uani 1 1 d . . . H21 H 0.4159 0.3379 0.4168 0.045 Uiso 1 1 calc R . . C22 C 0.47199(16) 0.33841(16) 0.50241(8) 0.0365(5) Uani 1 1 d . . . H22 H 0.5500 0.3100 0.4951 0.044 Uiso 1 1 calc R . . C23 C 0.43979(16) 0.36255(16) 0.56000(8) 0.0353(4) Uani 1 1 d . . . C24 C 0.32497(17) 0.40522(18) 0.56827(8) 0.0437(5) Uani 1 1 d . . . H24 H 0.3010 0.4241 0.6070 0.052 Uiso 1 1 calc R . . C25 C 0.24481(17) 0.42085(18) 0.52147(8) 0.0445(5) Uani 1 1 d . . . H25 H 0.1665 0.4485 0.5286 0.053 Uiso 1 1 calc R . . C26 C 0.52101(17) 0.35283(18) 0.61160(8) 0.0436(5) Uani 1 1 d . . . H26 H 0.4982 0.4000 0.6449 0.052 Uiso 1 1 calc R . . C27 C 0.62135(17) 0.28865(18) 0.61926(8) 0.0447(5) Uani 1 1 d . . . H27 H 0.6640 0.3025 0.6554 0.054 Uiso 1 1 calc R . . C28 C 0.67515(16) 0.19784(17) 0.57823(7) 0.0349(4) Uani 1 1 d . . . C29 C 0.78799(16) 0.21559(17) 0.55721(8) 0.0362(4) Uani 1 1 d . . . H29 H 0.8324 0.2873 0.5692 0.043 Uiso 1 1 calc R . . C30 C 0.83688(15) 0.13027(17) 0.51896(7) 0.0345(4) Uani 1 1 d . . . H30 H 0.9134 0.1455 0.5041 0.041 Uiso 1 1 calc R . . C31 C 0.77573(15) 0.02328(16) 0.50213(7) 0.0325(4) Uani 1 1 d . . . C32 C 0.66433(17) 0.00319(17) 0.52449(8) 0.0408(5) Uani 1 1 d . . . H32 H 0.6219 -0.0711 0.5144 0.049 Uiso 1 1 calc R . . C33 C 0.61432(16) 0.09006(18) 0.56130(8) 0.0402(5) Uani 1 1 d . . . H33 H 0.5370 0.0758 0.5753 0.048 Uiso 1 1 calc R . . C34 C 0.82906(16) -0.06827(18) 0.46067(8) 0.0430(5) Uani 1 1 d . . . H34A H 0.9070 -0.0375 0.4479 0.052 Uiso 1 1 calc R . . H34B H 0.8408 -0.1505 0.4802 0.052 Uiso 1 1 calc R . . O1 O 0.88004(11) -0.20432(12) 0.36616(5) 0.0457(3) Uani 1 1 d . . . O2 O 0.74703(10) -0.08033(12) 0.41032(5) 0.0409(3) Uani 1 1 d . . . O3 O 0.69872(11) -0.15955(12) 0.32608(5) 0.0418(3) Uani 1 1 d . . . O4 O 0.06511(10) 0.21175(12) 0.42302(5) 0.0411(3) Uani 1 1 d . . . O5 O 0.12284(10) 0.15568(11) 0.33241(5) 0.0384(3) Uani 1 1 d . . . O6 O 0.19001(11) 0.32753(12) 0.36898(5) 0.0401(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0399(12) 0.0357(11) 0.0302(11) -0.0001(9) 0.0003(9) 0.0023(9) C2 0.0476(12) 0.0508(12) 0.0310(11) -0.0104(10) 0.0017(9) 0.0100(10) C3 0.0395(11) 0.0385(11) 0.0265(10) -0.0027(9) 0.0039(8) -0.0016(9) C4 0.0444(12) 0.0383(11) 0.0387(11) -0.0022(10) 0.0075(10) 0.0048(10) C5 0.0468(12) 0.0359(11) 0.0389(11) -0.0115(10) 0.0086(10) -0.0076(10) C6 0.0398(11) 0.0385(11) 0.0252(10) -0.0027(9) 0.0070(8) -0.0084(9) C7 0.0393(11) 0.0337(10) 0.0346(11) -0.0020(9) -0.0010(9) -0.0016(9) C8 0.0428(11) 0.0343(11) 0.0343(11) -0.0073(9) -0.0012(9) -0.0042(9) C9 0.0454(12) 0.0468(12) 0.0297(11) -0.0103(9) 0.0041(9) -0.0139(10) C10 0.0421(12) 0.0533(13) 0.0284(10) -0.0072(10) -0.0018(9) -0.0151(10) C11 0.0306(10) 0.0414(11) 0.0308(11) -0.0044(9) -0.0022(8) -0.0118(9) C12 0.0352(11) 0.0506(12) 0.0277(10) 0.0033(10) -0.0053(8) -0.0075(10) C13 0.0333(11) 0.0423(11) 0.0380(11) 0.0020(10) -0.0022(9) -0.0016(9) C14 0.0291(10) 0.0376(11) 0.0315(11) 0.0004(9) 0.0006(8) -0.0071(8) C15 0.0416(11) 0.0448(12) 0.0278(10) 0.0043(9) -0.0008(9) -0.0017(10) C16 0.0466(12) 0.0369(11) 0.0367(11) 0.0012(10) 0.0029(9) -0.0001(9) C17 0.0340(11) 0.0406(11) 0.0384(11) 0.0013(9) 0.0033(9) -0.0055(9) C18 0.0286(10) 0.0436(12) 0.0303(11) -0.0006(10) -0.0041(9) 0.0046(9) C19 0.0524(13) 0.0396(12) 0.0425(12) -0.0135(10) -0.0057(10) 0.0043(10) C20 0.0414(11) 0.0312(10) 0.0349(11) -0.0058(9) -0.0009(9) 0.0001(9) C21 0.0472(12) 0.0368(11) 0.0291(10) -0.0048(9) 0.0054(9) 0.0022(9) C22 0.0368(11) 0.0373(11) 0.0356(11) -0.0018(9) 0.0052(9) 0.0046(9) C23 0.0393(11) 0.0338(10) 0.0328(11) -0.0069(9) 0.0017(9) -0.0009(9) C24 0.0452(12) 0.0538(13) 0.0324(11) -0.0119(10) 0.0059(10) 0.0049(10) C25 0.0372(11) 0.0552(13) 0.0412(12) -0.0120(10) 0.0018(10) 0.0064(10) C26 0.0472(12) 0.0501(12) 0.0335(11) -0.0101(10) 0.0024(10) 0.0069(10) C27 0.0488(12) 0.0549(13) 0.0299(11) -0.0093(10) -0.0059(9) 0.0062(11) C28 0.0405(11) 0.0390(11) 0.0248(10) 0.0010(9) -0.0051(8) 0.0050(9) C29 0.0386(11) 0.0339(10) 0.0356(11) 0.0002(9) -0.0067(9) -0.0018(9) C30 0.0320(10) 0.0408(11) 0.0305(10) 0.0059(9) -0.0030(8) 0.0016(9) C31 0.0368(11) 0.0352(10) 0.0250(10) 0.0019(9) -0.0060(8) 0.0061(9) C32 0.0464(12) 0.0318(11) 0.0438(12) -0.0008(9) -0.0027(10) -0.0053(9) C33 0.0377(11) 0.0432(12) 0.0401(11) 0.0044(10) 0.0062(9) -0.0026(9) C34 0.0443(12) 0.0509(13) 0.0330(11) -0.0050(10) -0.0122(9) 0.0115(10) O1 0.0361(8) 0.0570(9) 0.0438(8) -0.0097(7) -0.0018(6) 0.0103(7) O2 0.0446(8) 0.0472(8) 0.0303(7) -0.0093(6) -0.0086(6) 0.0124(6) O3 0.0440(8) 0.0517(8) 0.0292(7) -0.0109(6) -0.0068(6) 0.0126(7) O4 0.0360(7) 0.0599(9) 0.0276(7) -0.0006(7) 0.0028(6) 0.0036(6) O5 0.0423(8) 0.0432(8) 0.0301(7) -0.0066(6) 0.0057(6) -0.0092(6) O6 0.0449(8) 0.0415(8) 0.0338(7) -0.0068(6) 0.0010(6) -0.0051(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 1.192(2) . ? C1 O3 1.337(2) . ? C1 O2 1.337(2) . ? C2 O3 1.4498(19) . ? C2 C3 1.497(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.382(2) . ? C3 C8 1.386(2) . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 C7 1.392(2) . ? C6 C9 1.476(2) . ? C7 C8 1.382(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.326(2) . ? C9 H9 0.9500 . ? C10 C11 1.480(2) . ? C10 H10 0.9500 . ? C11 C12 1.388(2) . ? C11 C16 1.391(2) . ? C12 C13 1.381(2) . ? C12 H12 0.9500 . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 C17 1.497(2) . ? C15 C16 1.379(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O5 1.457(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O4 1.1996(19) . ? C18 O5 1.329(2) . ? C18 O6 1.335(2) . ? C19 O6 1.448(2) . ? C19 C20 1.500(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C25 1.381(2) . ? C20 C21 1.385(2) . ? C21 C22 1.382(2) . ? C21 H21 0.9500 . ? C22 C23 1.393(2) . ? C22 H22 0.9500 . ? C23 C24 1.391(2) . ? C23 C26 1.468(2) . ? C24 C25 1.383(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.329(2) . ? C26 H26 0.9500 . ? C27 C28 1.487(2) . ? C27 H27 0.9500 . ? C28 C29 1.386(2) . ? C28 C33 1.387(2) . ? C29 C30 1.385(2) . ? C29 H29 0.9500 . ? C30 C31 1.381(2) . ? C30 H30 0.9500 . ? C31 C32 1.387(2) . ? C31 C34 1.496(2) . ? C32 C33 1.381(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 O2 1.4532(19) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? 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 O3 126.77(17) . . ? O1 C1 O2 126.46(17) . . ? O3 C1 O2 106.77(15) . . ? O3 C2 C3 107.51(14) . . ? O3 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? O3 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C8 118.39(17) . . ? C4 C3 C2 120.33(17) . . ? C8 C3 C2 121.24(16) . . ? C3 C4 C5 120.71(18) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 121.30(17) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 117.61(17) . . ? C5 C6 C9 120.37(16) . . ? C7 C6 C9 121.90(17) . . ? C8 C7 C6 121.07(17) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 120.91(17) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? C10 C9 C6 128.55(17) . . ? C10 C9 H9 115.7 . . ? C6 C9 H9 115.7 . . ? C9 C10 C11 126.92(17) . . ? C9 C10 H10 116.5 . . ? C11 C10 H10 116.5 . . ? C12 C11 C16 117.74(17) . . ? C12 C11 C10 121.50(17) . . ? C16 C11 C10 120.75(17) . . ? C13 C12 C11 121.19(17) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.67(18) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 118.26(17) . . ? C15 C14 C17 120.46(16) . . ? C13 C14 C17 121.16(17) . . ? C16 C15 C14 121.04(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 120.93(18) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O5 C17 C14 105.49(13) . . ? O5 C17 H17A 110.6 . . ? C14 C17 H17A 110.6 . . ? O5 C17 H17B 110.6 . . ? C14 C17 H17B 110.6 . . ? H17A C17 H17B 108.8 . . ? O4 C18 O5 126.57(17) . . ? O4 C18 O6 126.47(17) . . ? O5 C18 O6 106.95(15) . . ? O6 C19 C20 113.64(15) . . ? O6 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? O6 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C25 C20 C21 118.23(17) . . ? C25 C20 C19 120.09(17) . . ? C21 C20 C19 121.54(17) . . ? C22 C21 C20 121.24(17) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 120.92(17) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 117.35(17) . . ? C24 C23 C26 118.33(16) . . ? C22 C23 C26 124.22(17) . . ? C25 C24 C23 121.57(17) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C20 C25 C24 120.69(18) . . ? C20 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C23 130.34(18) . . ? C27 C26 H26 114.8 . . ? C23 C26 H26 114.8 . . ? C26 C27 C28 128.04(18) . . ? C26 C27 H27 116.0 . . ? C28 C27 H27 116.0 . . ? C29 C28 C33 117.96(17) . . ? C29 C28 C27 121.63(17) . . ? C33 C28 C27 120.38(17) . . ? C30 C29 C28 120.97(17) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C31 C30 C29 120.77(17) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 118.44(17) . . ? C30 C31 C34 120.44(17) . . ? C32 C31 C34 121.12(17) . . ? C33 C32 C31 120.70(18) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C28 121.10(17) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? O2 C34 C31 107.15(14) . . ? O2 C34 H34A 110.3 . . ? C31 C34 H34A 110.3 . . ? O2 C34 H34B 110.3 . . ? C31 C34 H34B 110.3 . . ? H34A C34 H34B 108.5 . . ? C1 O2 C34 114.34(14) . . ? C1 O3 C2 114.91(14) . . ? C18 O5 C17 116.21(13) . . ? C18 O6 C19 115.63(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 O3 C2 C3 C4 -144.68(16) . . . . ? O3 C2 C3 C8 37.8(2) . . . . ? C8 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 C5 -177.20(16) . . . . ? C3 C4 C5 C6 -1.2(3) . . . . ? C4 C5 C6 C7 1.0(3) . . . . ? C4 C5 C6 C9 177.08(16) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C9 C6 C7 C8 -176.12(16) . . . . ? C6 C7 C8 C3 -0.6(3) . . . . ? C4 C3 C8 C7 0.5(3) . . . . ? C2 C3 C8 C7 178.06(16) . . . . ? C5 C6 C9 C10 146.0(2) . . . . ? C7 C6 C9 C10 -38.0(3) . . . . ? C6 C9 C10 C11 -7.2(3) . . . . ? C9 C10 C11 C12 134.5(2) . . . . ? C9 C10 C11 C16 -45.9(3) . . . . ? C16 C11 C12 C13 3.7(3) . . . . ? C10 C11 C12 C13 -176.69(16) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C15 -2.9(3) . . . . ? C12 C13 C14 C17 173.20(16) . . . . ? C13 C14 C15 C16 2.9(3) . . . . ? C17 C14 C15 C16 -173.20(16) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C12 C11 C16 C15 -3.7(3) . . . . ? C10 C11 C16 C15 176.71(16) . . . . ? C15 C14 C17 O5 111.77(17) . . . . ? C13 C14 C17 O5 -64.2(2) . . . . ? O6 C19 C20 C25 -138.05(18) . . . . ? O6 C19 C20 C21 46.4(2) . . . . ? C25 C20 C21 C22 -0.1(3) . . . . ? C19 C20 C21 C22 175.45(17) . . . . ? C20 C21 C22 C23 0.1(3) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C21 C22 C23 C26 -176.96(17) . . . . ? C22 C23 C24 C25 1.3(3) . . . . ? C26 C23 C24 C25 177.78(18) . . . . ? C21 C20 C25 C24 0.7(3) . . . . ? C19 C20 C25 C24 -174.94(18) . . . . ? C23 C24 C25 C20 -1.3(3) . . . . ? C24 C23 C26 C27 161.4(2) . . . . ? C22 C23 C26 C27 -22.3(3) . . . . ? C23 C26 C27 C28 -5.9(4) . . . . ? C26 C27 C28 C29 121.3(2) . . . . ? C26 C27 C28 C33 -60.7(3) . . . . ? C33 C28 C29 C30 2.1(3) . . . . ? C27 C28 C29 C30 -179.92(16) . . . . ? C28 C29 C30 C31 -1.9(3) . . . . ? C29 C30 C31 C32 -0.1(3) . . . . ? C29 C30 C31 C34 179.85(15) . . . . ? C30 C31 C32 C33 1.9(3) . . . . ? C34 C31 C32 C33 -178.01(16) . . . . ? C31 C32 C33 C28 -1.8(3) . . . . ? C29 C28 C33 C32 -0.2(3) . . . . ? C27 C28 C33 C32 -178.26(17) . . . . ? C30 C31 C34 O2 -122.37(17) . . . . ? C32 C31 C34 O2 57.6(2) . . . . ? O1 C1 O2 C34 -2.6(3) . . . . ? O3 C1 O2 C34 177.12(14) . . . . ? C31 C34 O2 C1 176.03(14) . . . . ? O1 C1 O3 C2 -1.5(3) . . . . ? O2 C1 O3 C2 178.74(14) . . . . ? C3 C2 O3 C1 173.30(15) . . . . ? O4 C18 O5 C17 3.2(2) . . . . ? O6 C18 O5 C17 -176.23(13) . . . . ? C14 C17 O5 C18 -174.12(14) . . . . ? O4 C18 O6 C19 -3.5(2) . . . . ? O5 C18 O6 C19 175.98(13) . . . . ? C20 C19 O6 C18 82.97(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.387 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.033 _database_code_depnum_ccdc_archive 'CCDC 957772' ####################################################################### # # 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_1CH2Cl2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H28 O6, C H2 Cl2' _chemical_formula_sum 'C35 H30 Cl2 O6' _chemical_formula_weight 617.49 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9128(8) _cell_length_b 11.6446(8) _cell_length_c 12.4210(9) _cell_angle_alpha 97.0810(10) _cell_angle_beta 100.5130(10) _cell_angle_gamma 98.8060(10) _cell_volume 1514.93(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7850 _cell_measurement_theta_min 2.262 _cell_measurement_theta_max 26.400 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.260 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21031 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5346 _reflns_number_gt 4186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics various _computing_publication_material 'SHELXTL Version 6.14 (Bruker, 2000)' _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^)+(0.0870P)^2^+0.1131P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5346 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.76690(16) 0.20336(15) 0.29587(13) 0.0252(4) Uani 1 1 d . . . C2 C 0.83374(18) 0.38018(15) 0.41712(13) 0.0293(4) Uani 1 1 d . . . H2A H 0.7646 0.4152 0.3781 0.035 Uiso 1 1 calc R . . H2B H 0.9098 0.4012 0.3858 0.035 Uiso 1 1 calc R . . C3 C 0.86216(16) 0.42753(15) 0.53919(13) 0.0254(4) Uani 1 1 d . . . C4 C 0.93551(17) 0.37624(16) 0.61659(14) 0.0292(4) Uani 1 1 d . . . H4 H 0.9645 0.3061 0.5937 0.035 Uiso 1 1 calc R . . C5 C 0.96662(17) 0.42737(16) 0.72760(14) 0.0308(4) Uani 1 1 d . . . H5 H 1.0174 0.3919 0.7798 0.037 Uiso 1 1 calc R . . C6 C 0.92480(16) 0.52929(16) 0.76337(13) 0.0276(4) Uani 1 1 d . . . C7 C 0.85027(17) 0.57939(16) 0.68492(14) 0.0303(4) Uani 1 1 d . . . H7 H 0.8199 0.6487 0.7078 0.036 Uiso 1 1 calc R . . C8 C 0.81998(17) 0.52943(16) 0.57425(14) 0.0289(4) Uani 1 1 d . . . H8 H 0.7699 0.5652 0.5219 0.035 Uiso 1 1 calc R . . C9 C 0.95894(18) 0.58730(17) 0.88087(15) 0.0335(4) Uani 1 1 d . . . H9 H 1.0462 0.6044 0.9155 0.040 Uiso 1 1 calc R . . C10 C 0.87657(19) 0.61719(17) 0.94139(14) 0.0342(5) Uani 1 1 d . . . H10 H 0.9102 0.6636 1.0121 0.041 Uiso 1 1 calc R . . C11 C 0.73791(18) 0.58444(16) 0.90793(13) 0.0288(4) Uani 1 1 d . . . C12 C 0.65956(19) 0.66714(16) 0.91936(14) 0.0327(4) Uani 1 1 d . . . H12 H 0.6962 0.7467 0.9489 0.039 Uiso 1 1 calc R . . C13 C 0.52840(18) 0.63487(16) 0.88806(13) 0.0312(4) Uani 1 1 d . . . H13 H 0.4768 0.6931 0.8940 0.037 Uiso 1 1 calc R . . C14 C 0.47228(18) 0.51849(15) 0.84823(13) 0.0270(4) Uani 1 1 d . . . C15 C 0.55010(19) 0.43544(16) 0.83841(14) 0.0320(4) Uani 1 1 d . . . H15 H 0.5132 0.3553 0.8119 0.038 Uiso 1 1 calc R . . C16 C 0.68009(18) 0.46776(16) 0.86664(14) 0.0316(4) Uani 1 1 d . . . H16 H 0.7314 0.4097 0.8579 0.038 Uiso 1 1 calc R . . C17 C 0.33080(18) 0.48368(16) 0.82075(13) 0.0307(4) Uani 1 1 d . . . H17A H 0.3023 0.4385 0.8769 0.037 Uiso 1 1 calc R . . H17B H 0.2917 0.5550 0.8218 0.037 Uiso 1 1 calc R . . C18 C 0.24003(16) 0.29957(15) 0.70712(14) 0.0253(4) Uani 1 1 d . . . C19 C 0.1656(2) 0.12368(16) 0.58436(14) 0.0360(5) Uani 1 1 d . . . H19A H 0.0858 0.1095 0.6118 0.043 Uiso 1 1 calc R . . H19B H 0.2275 0.0832 0.6264 0.043 Uiso 1 1 calc R . . C20 C 0.14148(17) 0.07562(15) 0.46298(14) 0.0284(4) Uani 1 1 d . . . C21 C 0.18792(18) -0.02449(16) 0.42999(14) 0.0322(4) Uani 1 1 d . . . H21 H 0.2390 -0.0582 0.4835 0.039 Uiso 1 1 calc R . . C22 C 0.16036(18) -0.07574(16) 0.31967(15) 0.0331(4) Uani 1 1 d . . . H22 H 0.1926 -0.1445 0.2983 0.040 Uiso 1 1 calc R . . C23 C 0.08602(17) -0.02768(16) 0.23978(14) 0.0290(4) Uani 1 1 d . . . C24 C 0.03938(17) 0.07215(17) 0.27331(15) 0.0327(4) Uani 1 1 d . . . H24 H -0.0120 0.1057 0.2199 0.039 Uiso 1 1 calc R . . C25 C 0.06686(17) 0.12372(16) 0.38403(15) 0.0317(4) Uani 1 1 d . . . H25 H 0.0344 0.1922 0.4057 0.038 Uiso 1 1 calc R . . C26 C 0.05757(18) -0.08407(17) 0.12188(15) 0.0351(5) Uani 1 1 d . . . H26 H -0.0289 -0.1028 0.0850 0.042 Uiso 1 1 calc R . . C27 C 0.14365(19) -0.11067(17) 0.06346(14) 0.0347(5) Uani 1 1 d . . . H27 H 0.1117 -0.1550 -0.0084 0.042 Uiso 1 1 calc R . . C28 C 0.28208(18) -0.07896(16) 0.09802(13) 0.0297(4) Uani 1 1 d . . . C29 C 0.35975(19) -0.15474(16) 0.06492(14) 0.0329(4) Uani 1 1 d . . . H29 H 0.3224 -0.2284 0.0202 0.039 Uiso 1 1 calc R . . C30 C 0.49060(18) -0.12504(16) 0.09586(13) 0.0307(4) Uani 1 1 d . . . H30 H 0.5415 -0.1793 0.0739 0.037 Uiso 1 1 calc R . . C31 C 0.54808(17) -0.01672(15) 0.15861(13) 0.0262(4) Uani 1 1 d . . . C32 C 0.47099(19) 0.06008(16) 0.19118(15) 0.0330(4) Uani 1 1 d . . . H32 H 0.5084 0.1345 0.2344 0.040 Uiso 1 1 calc R . . C33 C 0.34100(18) 0.02940(16) 0.16138(15) 0.0331(4) Uani 1 1 d . . . H33 H 0.2903 0.0833 0.1845 0.040 Uiso 1 1 calc R . . C34 C 0.68956(17) 0.01650(16) 0.18451(13) 0.0294(4) Uani 1 1 d . . . H34A H 0.7274 -0.0556 0.1826 0.035 Uiso 1 1 calc R . . H34B H 0.7174 0.0611 0.1277 0.035 Uiso 1 1 calc R . . O1 O 0.77001(13) 0.25313(11) 0.21698(10) 0.0371(3) Uani 1 1 d . . . O2 O 0.73329(12) 0.08809(10) 0.29357(9) 0.0300(3) Uani 1 1 d . . . O3 O 0.79641(11) 0.25351(10) 0.40162(9) 0.0269(3) Uani 1 1 d . . . O4 O 0.22103(14) 0.25229(11) 0.78449(10) 0.0398(4) Uani 1 1 d . . . O5 O 0.29081(12) 0.41193(10) 0.71107(9) 0.0305(3) Uani 1 1 d . . . O6 O 0.21490(11) 0.24918(10) 0.60133(9) 0.0268(3) Uani 1 1 d . . . C1S C 0.5152(2) 0.3299(2) 0.54701(19) 0.0592(7) Uani 1 1 d . . . H1SA H 0.5968 0.3817 0.5831 0.071 Uiso 1 1 calc R . . H1SB H 0.4480 0.3588 0.5808 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.52261(8) 0.18751(7) 0.57427(8) 0.0912(3) Uani 1 1 d . . . Cl2 Cl 0.48429(6) 0.34110(6) 0.40468(5) 0.0656(2) 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 0.0244(9) 0.0252(10) 0.0258(8) 0.0036(7) 0.0044(7) 0.0054(7) C2 0.0365(11) 0.0227(10) 0.0274(9) 0.0031(7) 0.0080(7) 0.0000(8) C3 0.0243(9) 0.0247(10) 0.0263(8) 0.0021(7) 0.0077(7) -0.0002(7) C4 0.0303(10) 0.0242(10) 0.0343(9) 0.0022(7) 0.0098(8) 0.0068(8) C5 0.0277(10) 0.0341(11) 0.0309(9) 0.0075(8) 0.0044(7) 0.0067(8) C6 0.0258(9) 0.0295(10) 0.0261(8) 0.0034(7) 0.0063(7) 0.0004(8) C7 0.0354(11) 0.0248(10) 0.0324(9) 0.0025(8) 0.0104(8) 0.0078(8) C8 0.0321(10) 0.0300(10) 0.0263(8) 0.0074(7) 0.0067(7) 0.0074(8) C9 0.0330(10) 0.0344(11) 0.0292(9) 0.0015(8) 0.0014(8) 0.0032(8) C10 0.0435(12) 0.0333(11) 0.0214(8) -0.0022(7) 0.0030(8) 0.0028(9) C11 0.0378(11) 0.0306(10) 0.0174(7) 0.0019(7) 0.0062(7) 0.0048(8) C12 0.0462(12) 0.0230(10) 0.0255(8) -0.0045(7) 0.0072(8) 0.0025(9) C13 0.0433(12) 0.0251(10) 0.0251(8) -0.0003(7) 0.0072(8) 0.0096(8) C14 0.0415(11) 0.0241(10) 0.0166(7) 0.0038(7) 0.0080(7) 0.0065(8) C15 0.0434(12) 0.0211(10) 0.0306(9) 0.0017(7) 0.0087(8) 0.0032(8) C16 0.0418(11) 0.0246(10) 0.0309(9) 0.0042(7) 0.0115(8) 0.0096(8) C17 0.0403(11) 0.0269(10) 0.0241(8) -0.0004(7) 0.0075(8) 0.0061(8) C18 0.0269(9) 0.0232(10) 0.0274(8) 0.0035(7) 0.0067(7) 0.0081(7) C19 0.0556(13) 0.0213(10) 0.0297(9) 0.0023(8) 0.0130(9) -0.0005(9) C20 0.0320(10) 0.0232(10) 0.0293(9) 0.0023(7) 0.0110(7) -0.0016(8) C21 0.0400(11) 0.0300(11) 0.0291(9) 0.0091(8) 0.0087(8) 0.0080(9) C22 0.0412(11) 0.0267(10) 0.0333(9) 0.0029(8) 0.0120(8) 0.0087(9) C23 0.0250(9) 0.0309(10) 0.0294(9) 0.0033(7) 0.0073(7) -0.0010(8) C24 0.0262(10) 0.0384(11) 0.0338(10) 0.0072(8) 0.0050(8) 0.0066(8) C25 0.0319(10) 0.0273(10) 0.0373(10) 0.0030(8) 0.0112(8) 0.0069(8) C26 0.0327(11) 0.0392(12) 0.0294(9) 0.0006(8) 0.0025(8) 0.0023(9) C27 0.0397(11) 0.0358(11) 0.0240(8) -0.0003(8) 0.0029(8) 0.0003(9) C28 0.0395(11) 0.0291(10) 0.0201(8) 0.0040(7) 0.0071(7) 0.0037(8) C29 0.0446(12) 0.0265(10) 0.0230(8) -0.0058(7) 0.0050(8) 0.0023(9) C30 0.0415(11) 0.0253(10) 0.0251(8) -0.0005(7) 0.0069(8) 0.0087(8) C31 0.0373(10) 0.0222(9) 0.0196(8) 0.0045(7) 0.0065(7) 0.0051(8) C32 0.0422(12) 0.0191(9) 0.0364(10) -0.0020(8) 0.0125(8) 0.0013(8) C33 0.0382(11) 0.0237(10) 0.0392(10) 0.0014(8) 0.0141(8) 0.0067(8) C34 0.0391(11) 0.0246(10) 0.0229(8) -0.0010(7) 0.0049(7) 0.0064(8) O1 0.0555(9) 0.0279(7) 0.0270(6) 0.0051(5) 0.0091(6) 0.0035(6) O2 0.0403(8) 0.0242(7) 0.0231(6) 0.0031(5) 0.0025(5) 0.0034(6) O3 0.0322(7) 0.0228(7) 0.0237(6) 0.0015(5) 0.0036(5) 0.0024(5) O4 0.0635(10) 0.0292(8) 0.0284(7) 0.0063(6) 0.0160(6) 0.0040(7) O5 0.0412(8) 0.0246(7) 0.0233(6) 0.0029(5) 0.0055(5) 0.0006(6) O6 0.0322(7) 0.0227(7) 0.0245(6) 0.0027(5) 0.0060(5) 0.0027(5) C1S 0.0560(15) 0.0668(17) 0.0587(14) 0.0138(12) 0.0224(12) 0.0067(12) Cl1 0.0798(6) 0.0780(5) 0.1273(7) 0.0323(5) 0.0223(5) 0.0356(4) Cl2 0.0652(4) 0.0819(5) 0.0524(4) -0.0007(3) 0.0133(3) 0.0294(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.201(2) . ? C1 O3 1.3300(19) . ? C1 O2 1.332(2) . ? C2 O3 1.448(2) . ? C2 C3 1.506(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.387(2) . ? C3 C4 1.389(2) . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 C7 1.396(2) . ? C6 C9 1.485(2) . ? C7 C8 1.384(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.331(3) . ? C9 H9 0.9500 . ? C10 C11 1.471(3) . ? C10 H10 0.9500 . ? C11 C12 1.393(3) . ? C11 C16 1.398(3) . ? C12 C13 1.392(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.390(3) . ? C14 C17 1.499(3) . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O5 1.4612(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O4 1.199(2) . ? C18 O5 1.332(2) . ? C18 O6 1.3324(19) . ? C19 O6 1.453(2) . ? C19 C20 1.502(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C25 1.386(3) . ? C20 C21 1.387(3) . ? C21 C22 1.385(2) . ? C21 H21 0.9500 . ? C22 C23 1.392(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(3) . ? C23 C26 1.486(2) . ? C24 C25 1.390(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.337(3) . ? C26 H26 0.9500 . ? C27 C28 1.468(3) . ? C27 H27 0.9500 . ? C28 C29 1.390(3) . ? C28 C33 1.395(3) . ? C29 C30 1.386(3) . ? C29 H29 0.9500 . ? C30 C31 1.389(2) . ? C30 H30 0.9500 . ? C31 C32 1.392(3) . ? C31 C34 1.497(3) . ? C32 C33 1.378(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 O2 1.4566(19) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C1S Cl1 1.743(3) . ? C1S Cl2 1.763(2) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? 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 O3 126.18(16) . . ? O1 C1 O2 126.36(15) . . ? O3 C1 O2 107.46(13) . . ? O3 C2 C3 109.13(13) . . ? O3 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? O3 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C8 C3 C4 119.13(15) . . ? C8 C3 C2 118.78(15) . . ? C4 C3 C2 121.98(16) . . ? C3 C4 C5 120.13(16) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 121.12(16) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 118.19(16) . . ? C5 C6 C9 122.29(16) . . ? C7 C6 C9 119.51(16) . . ? C8 C7 C6 120.91(17) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 120.52(16) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? C10 C9 C6 124.98(17) . . ? C10 C9 H9 117.5 . . ? C6 C9 H9 117.5 . . ? C9 C10 C11 125.46(16) . . ? C9 C10 H10 117.3 . . ? C11 C10 H10 117.3 . . ? C12 C11 C16 117.70(17) . . ? C12 C11 C10 121.52(16) . . ? C16 C11 C10 120.75(17) . . ? C13 C12 C11 120.97(17) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 120.67(17) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 118.48(17) . . ? C13 C14 C17 120.19(16) . . ? C15 C14 C17 121.28(16) . . ? C16 C15 C14 120.91(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 121.23(18) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? O5 C17 C14 109.71(14) . . ? O5 C17 H17A 109.7 . . ? C14 C17 H17A 109.7 . . ? O5 C17 H17B 109.7 . . ? C14 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? O4 C18 O5 126.37(16) . . ? O4 C18 O6 126.29(16) . . ? O5 C18 O6 107.34(13) . . ? O6 C19 C20 109.48(14) . . ? O6 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? O6 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? C25 C20 C21 119.11(16) . . ? C25 C20 C19 121.80(17) . . ? C21 C20 C19 118.94(16) . . ? C22 C21 C20 120.51(17) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.75(17) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 118.50(16) . . ? C24 C23 C26 121.62(16) . . ? C22 C23 C26 119.88(17) . . ? C23 C24 C25 120.85(17) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C20 C25 C24 120.28(17) . . ? C20 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C23 125.36(17) . . ? C27 C26 H26 117.3 . . ? C23 C26 H26 117.3 . . ? C26 C27 C28 127.23(16) . . ? C26 C27 H27 116.4 . . ? C28 C27 H27 116.4 . . ? C29 C28 C33 117.40(17) . . ? C29 C28 C27 120.84(16) . . ? C33 C28 C27 121.72(17) . . ? C30 C29 C28 121.33(16) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C29 C30 C31 120.69(17) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C32 118.31(17) . . ? C30 C31 C34 119.64(16) . . ? C32 C31 C34 121.98(15) . . ? C33 C32 C31 120.70(16) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C28 121.55(18) . . ? C32 C33 H33 119.2 . . ? C28 C33 H33 119.2 . . ? O2 C34 C31 110.46(14) . . ? O2 C34 H34A 109.6 . . ? C31 C34 H34A 109.6 . . ? O2 C34 H34B 109.6 . . ? C31 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C1 O2 C34 116.57(13) . . ? C1 O3 C2 113.72(12) . . ? C18 O5 C17 116.79(13) . . ? C18 O6 C19 113.79(13) . . ? Cl1 C1S Cl2 113.99(13) . . ? Cl1 C1S H1SA 108.8 . . ? Cl2 C1S H1SA 108.8 . . ? Cl1 C1S H1SB 108.8 . . ? Cl2 C1S H1SB 108.8 . . ? H1SA C1S H1SB 107.6 . . ? 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 O3 C2 C3 C8 -138.05(16) . . . . ? O3 C2 C3 C4 45.8(2) . . . . ? C8 C3 C4 C5 -0.4(3) . . . . ? C2 C3 C4 C5 175.66(16) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C4 C5 C6 C9 -178.58(17) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C9 C6 C7 C8 178.06(17) . . . . ? C6 C7 C8 C3 0.7(3) . . . . ? C4 C3 C8 C7 -0.1(3) . . . . ? C2 C3 C8 C7 -176.34(16) . . . . ? C5 C6 C9 C10 -127.9(2) . . . . ? C7 C6 C9 C10 53.4(3) . . . . ? C6 C9 C10 C11 8.6(3) . . . . ? C9 C10 C11 C12 -132.6(2) . . . . ? C9 C10 C11 C16 49.5(3) . . . . ? C16 C11 C12 C13 -1.6(2) . . . . ? C10 C11 C12 C13 -179.57(15) . . . . ? C11 C12 C13 C14 2.3(3) . . . . ? C12 C13 C14 C15 -1.2(2) . . . . ? C12 C13 C14 C17 176.59(15) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C17 C14 C15 C16 -178.27(15) . . . . ? C14 C15 C16 C11 1.2(3) . . . . ? C12 C11 C16 C15 -0.1(2) . . . . ? C10 C11 C16 C15 177.88(15) . . . . ? C13 C14 C17 O5 131.36(16) . . . . ? C15 C14 C17 O5 -50.9(2) . . . . ? O6 C19 C20 C25 -53.8(2) . . . . ? O6 C19 C20 C21 130.74(17) . . . . ? C25 C20 C21 C22 0.1(3) . . . . ? C19 C20 C21 C22 175.68(17) . . . . ? C20 C21 C22 C23 0.2(3) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C21 C22 C23 C26 -179.99(17) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C26 C23 C24 C25 179.95(17) . . . . ? C21 C20 C25 C24 -0.1(3) . . . . ? C19 C20 C25 C24 -175.58(16) . . . . ? C23 C24 C25 C20 -0.2(3) . . . . ? C24 C23 C26 C27 127.7(2) . . . . ? C22 C23 C26 C27 -52.8(3) . . . . ? C23 C26 C27 C28 -7.3(3) . . . . ? C26 C27 C28 C29 145.4(2) . . . . ? C26 C27 C28 C33 -37.0(3) . . . . ? C33 C28 C29 C30 1.5(3) . . . . ? C27 C28 C29 C30 179.14(16) . . . . ? C28 C29 C30 C31 -1.8(3) . . . . ? C29 C30 C31 C32 1.1(3) . . . . ? C29 C30 C31 C34 -175.92(16) . . . . ? C30 C31 C32 C33 -0.3(3) . . . . ? C34 C31 C32 C33 176.70(16) . . . . ? C31 C32 C33 C28 0.1(3) . . . . ? C29 C28 C33 C32 -0.6(3) . . . . ? C27 C28 C33 C32 -178.26(16) . . . . ? C30 C31 C34 O2 -146.34(15) . . . . ? C32 C31 C34 O2 36.7(2) . . . . ? O1 C1 O2 C34 -3.6(3) . . . . ? O3 C1 O2 C34 176.40(13) . . . . ? C31 C34 O2 C1 -102.44(17) . . . . ? O1 C1 O3 C2 0.6(2) . . . . ? O2 C1 O3 C2 -179.32(13) . . . . ? C3 C2 O3 C1 178.81(14) . . . . ? O4 C18 O5 C17 2.0(3) . . . . ? O6 C18 O5 C17 -177.64(14) . . . . ? C14 C17 O5 C18 112.79(16) . . . . ? O4 C18 O6 C19 -3.1(3) . . . . ? O5 C18 O6 C19 176.52(14) . . . . ? C20 C19 O6 C18 -179.60(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.588 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 957773' ####################################################################### # # 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_1THF _audit_creation_date 2013-03-21 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:17:34, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H28 O6, C4 H8 O' _chemical_formula_sum 'C38 H36 O7' _chemical_formula_weight 604.67 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.555(4) _cell_length_b 5.6690(16) _cell_length_c 18.310(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.521(6) _cell_angle_gamma 90.00 _cell_volume 1501.0(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2790 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.96 _cell_measurement_theta_min 2.24 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.790043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.1299 before and 0.0400 after correction. The Ratio of minimum to maximum transmission is 0.7900. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w and \f scans each set at different \f and/or \w angles and each scan (15 s exposure) covering -0.450\% degrees. The crystal to detector distance was 4.956 cm. ; _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_unetI/netI 0.0373 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 16358 _diffrn_reflns_theta_full 26.60 _diffrn_reflns_theta_max 26.60 _diffrn_reflns_theta_min 1.70 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 37.0 _diffrn_source_power 1.739 _diffrn_source_target Mo _diffrn_source_voltage 47.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2524 _reflns_number_total 3122 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection ? _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.241 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3122 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0416 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.4603P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1011 _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. _olex2_refinement_description 1. Fixed Uiso At 1.2 times of: {H2A,H2B} of C2, H8 of C8, H9 of C9, H10 of C10, H12 of C12, H13 of C13, H15 of C15, H16 of C16, {H17A,H17B} of C17, {H21A,H21B} of C21, H7 of C7, {H24A,H24B} of C24, {H23A,H23B} of C23, {H22A,H22B} of C22, H4 of C4, H5 of C5 2. Restrained distances C23-C22 1.55 with sigma of 0.02 C23-C22 1.54 with sigma of 0.015 O21-C24 \~ O21-C21 with sigma of 0.02 C24-C23 \~ C22-C21 with sigma of 0.02 3. Others Fixed Sof: O21(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5) H24B(0.5) 4.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C17(H17A,H17B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B) 4.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.46464(7) 0.33470(19) 0.22160(5) 0.0247(3) Uani 1 1 d . . . O2 O 0.46586(7) -0.00790(18) 0.28520(5) 0.0225(2) Uani 1 1 d . . . O3 O 0.36451(7) 0.25202(17) 0.30394(5) 0.0212(2) Uani 1 1 d . . . C1 C 0.43470(10) 0.2068(3) 0.26523(7) 0.0199(3) Uani 1 1 d . . . C2 C 0.32421(10) 0.4849(3) 0.29146(8) 0.0227(3) Uani 1 1 d . . . H2A H 0.2844 0.4877 0.2439 0.027 Uiso 1 1 calc R . . H2B H 0.3739 0.6032 0.2894 0.027 Uiso 1 1 calc R . . C3 C 0.26806(10) 0.5447(3) 0.35248(8) 0.0207(3) Uani 1 1 d . . . C4 C 0.19397(10) 0.4070(3) 0.36842(8) 0.0242(3) Uani 1 1 d . . . H4 H 0.1814 0.2623 0.3431 0.029 Uiso 1 1 calc R . . C5 C 0.13858(10) 0.4778(3) 0.42053(8) 0.0247(3) Uani 1 1 d . . . H5 H 0.0880 0.3814 0.4303 0.030 Uiso 1 1 calc R . . C6 C 0.15523(10) 0.6877(3) 0.45913(8) 0.0215(3) Uani 1 1 d . . . C7 C 0.23013(10) 0.8234(3) 0.44382(8) 0.0229(3) Uani 1 1 d . . . H7 H 0.2434 0.9666 0.4698 0.027 Uiso 1 1 calc R . . C8 C 0.28573(10) 0.7533(3) 0.39131(8) 0.0227(3) Uani 1 1 d . . . H8 H 0.3366 0.8489 0.3817 0.027 Uiso 1 1 calc R . . C9 C 0.08967(10) 0.7683(3) 0.50969(8) 0.0236(3) Uani 1 1 d . . . H9 H 0.0265 0.7334 0.4947 0.028 Uiso 1 1 calc R . . C10 C 0.10640(10) 0.8831(3) 0.57333(8) 0.0242(3) Uani 1 1 d . . . H10 H 0.0535 0.9372 0.5944 0.029 Uiso 1 1 calc R . . C11 C 0.19658(10) 0.9368(3) 0.61512(8) 0.0213(3) Uani 1 1 d . . . C12 C 0.20958(11) 1.1460(3) 0.65444(8) 0.0245(3) Uani 1 1 d . . . H12 H 0.1603 1.2564 0.6531 0.029 Uiso 1 1 calc R . . C13 C 0.29301(10) 1.1964(3) 0.69557(8) 0.0234(3) Uani 1 1 d . . . H13 H 0.3008 1.3425 0.7209 0.028 Uiso 1 1 calc R . . C14 C 0.36546(10) 1.0357(3) 0.70026(8) 0.0205(3) Uani 1 1 d . . . C15 C 0.35225(10) 0.8247(3) 0.66223(8) 0.0215(3) Uani 1 1 d . . . H15 H 0.4007 0.7117 0.6652 0.026 Uiso 1 1 calc R . . C16 C 0.26967(10) 0.7766(3) 0.62022(8) 0.0218(3) Uani 1 1 d . . . H16 H 0.2625 0.6315 0.5942 0.026 Uiso 1 1 calc R . . C17 C 0.45419(10) 1.0900(3) 0.74807(8) 0.0230(3) Uani 1 1 d . . . H17A H 0.4591 1.2624 0.7561 0.028 Uiso 1 1 calc R . . H17B H 0.4531 1.0133 0.7965 0.028 Uiso 1 1 calc R . . O21 O 0.50010(16) 0.4863(4) 0.41321(12) 0.0306(5) Uani 0.50 1 d PD A -1 C21 C 0.5473(4) 0.6674(9) 0.4553(3) 0.0358(12) Uani 0.50 1 d PD A -1 H21A H 0.5394 0.8198 0.4289 0.043 Uiso 0.50 1 calc PR A -1 H21B H 0.6141 0.6312 0.4642 0.043 Uiso 0.50 1 calc PR A -1 C22 C 0.5063(11) 0.680(2) 0.5268(7) 0.044(4) Uani 0.50 1 d PD A -1 H22A H 0.4582 0.8044 0.5253 0.053 Uiso 0.50 1 calc PR A -1 H22B H 0.5545 0.7130 0.5682 0.053 Uiso 0.50 1 calc PR A -1 C23 C 0.4639(5) 0.4325(9) 0.5339(3) 0.0402(13) Uani 0.50 1 d PD A -1 H23A H 0.4899 0.3541 0.5800 0.048 Uiso 0.50 1 calc PR A -1 H23B H 0.3958 0.4408 0.5326 0.048 Uiso 0.50 1 calc PR A -1 C24 C 0.4920(9) 0.3044(19) 0.4668(6) 0.037(3) Uani 0.50 1 d PD A -1 H24A H 0.5517 0.2218 0.4789 0.044 Uiso 0.50 1 calc PR A -1 H24B H 0.4444 0.1875 0.4483 0.044 Uiso 0.50 1 calc PR A -1 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(6) 0.0236(6) 0.0247(5) 0.0014(4) 0.0073(4) -0.0043(5) O2 0.0209(5) 0.0203(6) 0.0272(5) 0.0009(4) 0.0069(4) -0.0001(4) O3 0.0211(5) 0.0201(6) 0.0230(5) 0.0021(4) 0.0058(4) 0.0005(4) C1 0.0189(7) 0.0213(8) 0.0193(7) -0.0022(6) 0.0011(6) -0.0044(6) C2 0.0247(8) 0.0196(8) 0.0240(7) 0.0036(6) 0.0036(6) 0.0013(6) C3 0.0201(7) 0.0225(8) 0.0189(7) 0.0043(6) -0.0006(6) 0.0022(6) C4 0.0263(8) 0.0219(8) 0.0240(7) -0.0025(6) 0.0019(6) -0.0030(6) C5 0.0208(8) 0.0275(9) 0.0262(8) 0.0003(6) 0.0035(6) -0.0053(6) C6 0.0193(7) 0.0246(8) 0.0203(7) 0.0037(6) 0.0002(6) 0.0043(6) C7 0.0276(8) 0.0189(8) 0.0219(7) -0.0009(6) 0.0013(6) 0.0002(6) C8 0.0232(8) 0.0221(8) 0.0228(7) 0.0039(6) 0.0022(6) -0.0023(6) C9 0.0189(7) 0.0259(8) 0.0260(8) 0.0020(6) 0.0020(6) 0.0012(6) C10 0.0217(8) 0.0251(8) 0.0267(8) 0.0021(6) 0.0066(6) 0.0057(6) C11 0.0230(8) 0.0224(8) 0.0195(7) 0.0032(6) 0.0065(6) 0.0019(6) C12 0.0270(8) 0.0226(8) 0.0250(8) 0.0007(6) 0.0077(6) 0.0073(7) C13 0.0302(8) 0.0167(8) 0.0244(7) -0.0022(6) 0.0083(6) 0.0007(6) C14 0.0230(8) 0.0203(8) 0.0196(7) 0.0020(6) 0.0084(6) -0.0025(6) C15 0.0222(8) 0.0195(8) 0.0237(7) 0.0001(6) 0.0065(6) 0.0032(6) C16 0.0273(8) 0.0178(7) 0.0210(7) -0.0014(6) 0.0057(6) 0.0016(6) C17 0.0226(8) 0.0215(8) 0.0260(8) -0.0045(6) 0.0084(6) -0.0013(6) O21 0.0409(14) 0.0275(13) 0.0235(12) -0.0005(10) 0.0046(10) 0.0042(10) C21 0.039(3) 0.041(3) 0.030(3) -0.002(2) 0.0109(19) 0.000(3) C22 0.064(7) 0.032(5) 0.035(4) -0.010(4) -0.004(4) 0.008(4) C23 0.040(3) 0.048(4) 0.034(3) 0.007(3) 0.013(2) 0.004(3) C24 0.049(7) 0.032(5) 0.036(5) 0.010(3) 0.029(5) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1970(17) . ? O2 C1 1.3353(18) . ? O2 C17 1.4501(17) 3_666 ? O3 C1 1.3327(17) . ? O3 C2 1.4524(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.496(2) . ? C3 C4 1.389(2) . ? C3 C8 1.388(2) . ? C4 H4 0.9500 . ? C4 C5 1.377(2) . ? C5 H5 0.9500 . ? C5 C6 1.391(2) . ? C6 C7 1.388(2) . ? C6 C9 1.475(2) . ? C7 H7 0.9500 . ? C7 C8 1.383(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.333(2) . ? C10 H10 0.9500 . ? C10 C11 1.474(2) . ? C11 C12 1.389(2) . ? C11 C16 1.394(2) . ? C12 H12 0.9500 . ? C12 C13 1.384(2) . ? C13 H13 0.9500 . ? C13 C14 1.389(2) . ? C14 C15 1.387(2) . ? C14 C17 1.507(2) . ? C15 H15 0.9500 . ? C15 C16 1.379(2) . ? C16 H16 0.9500 . ? C17 O2 1.4501(17) 3_666 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O21 C21 1.414(6) . ? O21 C24 1.438(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.502(10) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.547(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.523(10) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C17 116.19(11) . 3_666 ? C1 O3 C2 114.31(11) . . ? O1 C1 O2 126.64(14) . . ? O1 C1 O3 126.69(14) . . ? O3 C1 O2 106.67(11) . . ? O3 C2 H2A 109.8 . . ? O3 C2 H2B 109.8 . . ? O3 C2 C3 109.49(11) . . ? H2A C2 H2B 108.2 . . ? C3 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C4 C3 C2 122.18(14) . . ? C8 C3 C2 119.36(13) . . ? C8 C3 C4 118.30(14) . . ? C3 C4 H4 119.6 . . ? C5 C4 C3 120.76(14) . . ? C5 C4 H4 119.6 . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.29(14) . . ? C6 C5 H5 119.4 . . ? C5 C6 C9 119.73(14) . . ? C7 C6 C5 117.81(14) . . ? C7 C6 C9 122.26(14) . . ? C6 C7 H7 119.5 . . ? C8 C7 C6 121.06(14) . . ? C8 C7 H7 119.5 . . ? C3 C8 H8 119.6 . . ? C7 C8 C3 120.76(14) . . ? C7 C8 H8 119.6 . . ? C6 C9 H9 115.4 . . ? C10 C9 C6 129.26(14) . . ? C10 C9 H9 115.4 . . ? C9 C10 H10 115.9 . . ? C9 C10 C11 128.18(14) . . ? C11 C10 H10 115.9 . . ? C12 C11 C10 120.40(13) . . ? C12 C11 C16 117.61(14) . . ? C16 C11 C10 121.89(14) . . ? C11 C12 H12 119.4 . . ? C13 C12 C11 121.17(14) . . ? C13 C12 H12 119.4 . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.76(14) . . ? C14 C13 H13 119.6 . . ? C13 C14 C17 119.77(13) . . ? C15 C14 C13 118.28(14) . . ? C15 C14 C17 121.91(13) . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.88(14) . . ? C16 C15 H15 119.6 . . ? C11 C16 H16 119.4 . . ? C15 C16 C11 121.26(14) . . ? C15 C16 H16 119.4 . . ? O2 C17 C14 111.47(12) 3_666 . ? O2 C17 H17A 109.3 3_666 . ? O2 C17 H17B 109.3 3_666 . ? C14 C17 H17A 109.3 . . ? C14 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C21 O21 C24 102.8(6) . . ? O21 C21 H21A 110.3 . . ? O21 C21 H21B 110.3 . . ? O21 C21 C22 107.1(6) . . ? H21A C21 H21B 108.5 . . ? C22 C21 H21A 110.3 . . ? C22 C21 H21B 110.3 . . ? C21 C22 H22A 111.1 . . ? C21 C22 H22B 111.1 . . ? C21 C22 C23 103.3(7) . . ? H22A C22 H22B 109.1 . . ? C23 C22 H22A 111.1 . . ? C23 C22 H22B 111.1 . . ? C22 C23 H23A 111.2 . . ? C22 C23 H23B 111.2 . . ? H23A C23 H23B 109.1 . . ? C24 C23 C22 102.7(5) . . ? C24 C23 H23A 111.2 . . ? C24 C23 H23B 111.2 . . ? O21 C24 C23 105.0(7) . . ? O21 C24 H24A 110.7 . . ? O21 C24 H24B 110.7 . . ? C23 C24 H24A 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? 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 O3 C2 C3 C4 -58.88(17) . . . . ? O3 C2 C3 C8 125.91(14) . . . . ? C1 O3 C2 C3 -162.66(12) . . . . ? C2 O3 C1 O1 -1.8(2) . . . . ? C2 O3 C1 O2 177.50(11) . . . . ? C2 C3 C4 C5 -174.15(14) . . . . ? C2 C3 C8 C7 174.54(13) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C4 C3 C8 C7 -0.9(2) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C4 C5 C6 C9 174.55(14) . . . . ? C5 C6 C7 C8 0.7(2) . . . . ? C5 C6 C9 C10 145.18(17) . . . . ? C6 C7 C8 C3 0.0(2) . . . . ? C6 C9 C10 C11 -7.9(3) . . . . ? C7 C6 C9 C10 -40.0(2) . . . . ? C8 C3 C4 C5 1.1(2) . . . . ? C9 C6 C7 C8 -174.16(13) . . . . ? C9 C10 C11 C12 145.35(16) . . . . ? C9 C10 C11 C16 -38.3(2) . . . . ? C10 C11 C12 C13 178.25(14) . . . . ? C10 C11 C16 C15 -177.01(13) . . . . ? C11 C12 C13 C14 -1.7(2) . . . . ? C12 C11 C16 C15 -0.6(2) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 C17 -177.31(13) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? C13 C14 C17 O2 -142.73(13) . . . 3_666 ? C14 C15 C16 C11 -0.6(2) . . . . ? C15 C14 C17 O2 39.54(19) . . . 3_666 ? C16 C11 C12 C13 1.7(2) . . . . ? C17 O2 C1 O1 1.9(2) 3_666 . . . ? C17 O2 C1 O3 -177.36(11) 3_666 . . . ? C17 C14 C15 C16 178.44(13) . . . . ? O21 C21 C22 C23 23.0(11) . . . . ? C21 O21 C24 C23 43.3(9) . . . . ? C21 C22 C23 C24 3.4(16) . . . . ? C22 C23 C24 O21 -28.2(15) . . . . ? C24 O21 C21 C22 -41.6(5) . . . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 957774'