# Electronic Supplementary Material (ESI) for CrystEngComm # 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_e2197a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H14 O4),0.5(C4 H8 O2),3(H2 O)' _chemical_formula_sum 'C38 H38 O12' _chemical_formula_weight 686.68 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 _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 15.0657(3) _cell_length_b 9.2696(2) _cell_length_c 28.1087(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.7970(10) _cell_angle_gamma 90.00 _cell_volume 3923.53(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5561 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9905 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details sadabs _exptl_special_details ; the squeeze command was used because of the flopiness of the solvents ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9642 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.34 _reflns_number_total 9642 _reflns_number_gt 6188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1740P)^2^+1.0108P] 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 9642 _refine_ls_number_parameters 506 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0820 _refine_ls_wR_factor_ref 0.2763 _refine_ls_wR_factor_gt 0.2526 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.056 _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 0.24578(18) -0.0145(2) 0.43423(8) 0.0222(5) Uani 1 1 d . . . C2 C 0.25501(17) -0.1478(2) 0.41174(8) 0.0231(5) Uani 1 1 d . . . H2 H 0.2623 -0.2331 0.4302 0.028 Uiso 1 1 calc R . . C3 C 0.25346(18) -0.1553(3) 0.36265(8) 0.0240(5) Uani 1 1 d . . . O1 O 0.26232(15) -0.29033(18) 0.34245(6) 0.0347(5) Uani 1 1 d . . . H1 H 0.2609 -0.2827 0.3127 0.052 Uiso 1 1 calc R . . C4 C 0.24255(19) -0.0337(3) 0.33467(8) 0.0273(6) Uani 1 1 d . . . H4 H 0.2419 -0.0402 0.3009 0.033 Uiso 1 1 calc R . . C5 C 0.23254(18) 0.0981(3) 0.35724(8) 0.0254(5) Uani 1 1 d . . . O2 O 0.21969(15) 0.21674(19) 0.32832(6) 0.0254(5) Uani 1 1 d . . . H2A H 0.2061 0.2882 0.3450 0.033 Uiso 1 1 calc R . . C6 C 0.23409(19) 0.1093(2) 0.40628(8) 0.0252(5) Uani 1 1 d . . . H6 H 0.2273 0.2008 0.4210 0.030 Uiso 1 1 calc R . . C7 C 0.24573(18) -0.0047(2) 0.48703(8) 0.0227(5) Uani 1 1 d . . . C8 C 0.21200(18) -0.1171(2) 0.51422(8) 0.0245(5) Uani 1 1 d . . . H8 H 0.1901 -0.2017 0.4988 0.029 Uiso 1 1 calc R . . C9 C 0.21019(18) -0.1065(2) 0.56330(8) 0.0244(5) Uani 1 1 d . . . H9 H 0.1870 -0.1842 0.5811 0.029 Uiso 1 1 calc R . . C10 C 0.24178(18) 0.0160(2) 0.58717(8) 0.0234(5) Uani 1 1 d . . . C11 C 0.27538(19) 0.1277(3) 0.56015(8) 0.0270(6) Uani 1 1 d . . . H11 H 0.2972 0.2122 0.5756 0.032 Uiso 1 1 calc R . . C12 C 0.27772(19) 0.1179(3) 0.51086(8) 0.0262(6) Uani 1 1 d . . . H12 H 0.3013 0.1955 0.4932 0.031 Uiso 1 1 calc R . . C13 C 0.23906(19) 0.0252(3) 0.63994(8) 0.0249(5) Uani 1 1 d . . . C14 C 0.25178(19) -0.0984(3) 0.66757(8) 0.0272(6) Uani 1 1 d . . . H14 H 0.2639 -0.1881 0.6528 0.033 Uiso 1 1 calc R . . C15 C 0.2467(2) -0.0899(3) 0.71665(8) 0.0298(6) Uani 1 1 d . . . O3 O 0.25855(17) -0.2100(2) 0.74503(6) 0.0430(6) Uani 1 1 d . . . H3 H 0.2650 -0.2831 0.7278 0.065 Uiso 1 1 calc R . . C16 C 0.2321(2) 0.0397(3) 0.73919(8) 0.0320(6) Uani 1 1 d . . . H16 H 0.2299 0.0447 0.7729 0.038 Uiso 1 1 calc R . . C17 C 0.2205(2) 0.1624(3) 0.71158(8) 0.0330(6) Uani 1 1 d . . . O4 O 0.20519(19) 0.2948(2) 0.73178(7) 0.0507(7) Uani 1 1 d . . . H4A H 0.2051 0.2863 0.7615 0.076 Uiso 1 1 calc R . . C18 C 0.2237(2) 0.1566(3) 0.66224(8) 0.0297(6) Uani 1 1 d . . . H18 H 0.2155 0.2418 0.6438 0.036 Uiso 1 1 calc R . . C19 C 0.00652(18) -0.0007(2) 0.39689(7) 0.0228(5) Uani 1 1 d . . . C20 C 0.02258(18) -0.1287(3) 0.37268(8) 0.0256(5) Uani 1 1 d . . . H20 H 0.0328 -0.2156 0.3899 0.031 Uiso 1 1 calc R . . C21 C 0.0235(2) -0.1290(3) 0.32326(8) 0.0281(6) Uani 1 1 d . . . O5 O 0.04143(16) -0.25737(19) 0.30131(6) 0.0391(5) Uani 1 1 d . . . H5 H 0.0392 -0.2458 0.2717 0.059 Uiso 1 1 calc R . . C22 C 0.0087(2) -0.0036(3) 0.29708(8) 0.0305(6) Uani 1 1 d . . . H22 H 0.0092 -0.0048 0.2633 0.037 Uiso 1 1 calc R . . C23 C -0.0068(2) 0.1232(3) 0.32159(8) 0.0296(6) Uani 1 1 d . . . O6 O -0.02177(18) 0.2439(2) 0.29418(6) 0.0296(6) Uani 1 1 d . . . H6A H -0.0163 0.3179 0.3112 0.0296(6) Uiso 1 1 calc R . . C24 C -0.00820(19) 0.1260(3) 0.37076(8) 0.0263(6) Uani 1 1 d . . . H24 H -0.0192 0.2141 0.3868 0.032 Uiso 1 1 calc R . . C25 C 0.00401(18) -0.0003(2) 0.44963(7) 0.0226(5) Uani 1 1 d . . . C26 C 0.02981(18) 0.1203(2) 0.47624(8) 0.0248(5) Uani 1 1 d . . . H26 H 0.0504 0.2038 0.4604 0.030 Uiso 1 1 calc R . . C27 C -0.02589(18) -0.1205(3) 0.47436(8) 0.0250(5) Uani 1 1 d . . . H27 H -0.0439 -0.2042 0.4571 0.030 Uiso 1 1 calc R . . C28 C 0.31236(19) 0.5054(3) 0.51840(9) 0.0272(6) Uani 1 1 d . . . C29 C 0.25021(18) 0.4943(3) 0.48085(9) 0.0263(5) Uani 1 1 d . . . H29 H 0.2691 0.4859 0.4490 0.032 Uiso 1 1 calc R . . C30 C 0.16030(19) 0.4956(3) 0.49042(9) 0.0276(6) Uani 1 1 d . . . O7 O 0.09677(14) 0.4847(2) 0.45453(7) 0.0375(5) Uani 1 1 d . . . H7 H 0.1214 0.4838 0.4281 0.056 Uiso 1 1 calc R . . C31 C 0.13068(19) 0.5079(3) 0.53626(10) 0.0282(6) Uani 1 1 d . . . H31 H 0.0690 0.5083 0.5424 0.034 Uiso 1 1 calc R . . C32 C 0.19385(19) 0.5196(3) 0.57297(9) 0.0283(6) Uani 1 1 d . . . O8 O 0.16258(14) 0.5359(2) 0.61813(7) 0.0374(5) Uani 1 1 d . . . H8A H 0.2055 0.5375 0.6379 0.056 Uiso 1 1 calc R . . C33 C 0.28362(19) 0.5181(3) 0.56510(9) 0.0280(6) Uani 1 1 d . . . H33 H 0.3254 0.5255 0.5910 0.034 Uiso 1 1 calc R . . C34 C 0.40839(19) 0.5031(3) 0.50895(9) 0.0288(6) Uani 1 1 d . . . C35 C 0.4432(2) 0.5749(3) 0.46992(10) 0.0345(6) Uani 1 1 d . . . H35 H 0.4042 0.6267 0.4489 0.041 Uiso 1 1 calc R . . C36 C 0.4682(2) 0.4279(3) 0.53869(10) 0.0348(6) Uani 1 1 d . . . H36 H 0.4467 0.3776 0.5654 0.042 Uiso 1 1 calc R . . C37 C 0.5884(4) 0.5668(9) 0.6577(3) 0.0542(18) Uani 0.50 1 d PD . . H37A H 0.6236 0.6267 0.6800 0.081 Uiso 0.50 1 calc PR . . H37B H 0.6246 0.5402 0.6307 0.081 Uiso 0.50 1 calc PR . . H37C H 0.5692 0.4792 0.6740 0.081 Uiso 0.50 1 calc PR . . C38 C 0.5101(6) 0.6479(9) 0.6404(3) 0.061(2) Uani 0.50 1 d PD . . O9 O 0.4358(3) 0.6177(8) 0.6537(2) 0.0723(18) Uani 0.50 1 d P . . O10 O 0.5331(3) 0.7475(6) 0.6099(2) 0.0650(15) Uani 0.50 1 d P . . C39 C 0.4633(6) 0.8326(9) 0.5847(4) 0.081(3) Uani 0.50 1 d PD . . H39A H 0.4357 0.7751 0.5586 0.097 Uiso 0.50 1 calc PR . . H39B H 0.4165 0.8599 0.6070 0.097 Uiso 0.50 1 calc PR . . C40 C 0.5030(6) 0.9560(17) 0.5665(5) 0.081(3) Uani 0.50 1 d PD . . H40A H 0.5428 0.9986 0.5909 0.097 Uiso 0.50 1 calc PR . . H40B H 0.4569 1.0261 0.5572 0.097 Uiso 0.50 1 calc PR . . H40C H 0.5371 0.9301 0.5387 0.097 Uiso 0.50 1 calc PR . . O11 O 0.27695(17) 0.5397(2) 0.69431(7) 0.0425(5) Uani 1 1 d D . . O12 O 0.00801(15) -0.0048(2) 0.16057(7) 0.0347(5) Uani 1 1 d D . . O14 O 0.16525(15) 0.4690(2) 0.36589(7) 0.0361(5) Uani 1 1 d D . . H11A H 0.245(3) 0.474(4) 0.7053(18) 0.092 Uiso 1 1 d D . . H11B H 0.3290(17) 0.539(5) 0.6857(18) 0.092 Uiso 1 1 d D . . H12A H 0.0562(19) -0.004(4) 0.1451(13) 0.063 Uiso 1 1 d D . . H12B H -0.002(2) 0.061(4) 0.1819(11) 0.063 Uiso 1 1 d D . . H14A H 0.1105(14) 0.471(4) 0.3547(14) 0.068 Uiso 1 1 d D . . H14B H 0.201(2) 0.539(3) 0.3611(15) 0.068 Uiso 1 1 d 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 0.0368(15) 0.0183(11) 0.0115(10) 0.0007(8) 0.0014(9) -0.0013(10) C2 0.0376(15) 0.0182(11) 0.0136(10) 0.0014(8) 0.0006(9) 0.0023(10) C3 0.0383(15) 0.0195(11) 0.0141(10) -0.0026(8) 0.0016(9) 0.0000(10) O1 0.0716(15) 0.0194(9) 0.0131(8) -0.0031(6) 0.0036(8) 0.0009(9) C4 0.0459(17) 0.0255(12) 0.0104(10) -0.0008(8) 0.0017(10) -0.0028(11) C5 0.0442(16) 0.0197(11) 0.0124(10) 0.0044(8) 0.0021(10) 0.0010(10) O2 0.0442(16) 0.0197(11) 0.0124(10) 0.0044(8) 0.0021(10) 0.0010(10) C6 0.0463(16) 0.0179(11) 0.0114(10) 0.0000(8) 0.0027(10) 0.0015(10) C7 0.0387(15) 0.0198(11) 0.0097(9) -0.0005(8) 0.0022(9) 0.0038(10) C8 0.0430(16) 0.0166(11) 0.0139(10) -0.0017(8) 0.0020(10) -0.0011(10) C9 0.0433(16) 0.0168(11) 0.0132(10) 0.0011(8) 0.0036(9) -0.0005(10) C10 0.0395(15) 0.0190(11) 0.0116(10) 0.0000(8) 0.0005(9) 0.0010(10) C11 0.0494(17) 0.0187(11) 0.0129(10) -0.0022(8) -0.0008(10) -0.0033(11) C12 0.0481(17) 0.0178(11) 0.0128(10) 0.0019(8) 0.0030(10) -0.0034(10) C13 0.0429(16) 0.0203(11) 0.0115(10) -0.0023(8) 0.0022(9) -0.0019(10) C14 0.0491(17) 0.0202(11) 0.0124(10) -0.0013(8) 0.0019(10) -0.0005(11) C15 0.0534(18) 0.0229(12) 0.0129(10) 0.0033(9) -0.0001(10) -0.0016(11) O3 0.0964(18) 0.0222(9) 0.0105(8) 0.0032(6) 0.0024(9) 0.0047(10) C16 0.061(2) 0.0256(12) 0.0091(10) -0.0022(9) 0.0035(11) -0.0026(12) C17 0.066(2) 0.0204(12) 0.0131(11) -0.0042(9) 0.0039(11) -0.0011(12) O4 0.118(2) 0.0195(9) 0.0151(8) -0.0030(7) 0.0071(11) 0.0052(11) C18 0.0581(19) 0.0190(11) 0.0121(10) 0.0001(8) 0.0035(10) -0.0018(11) C19 0.0387(15) 0.0221(11) 0.0074(9) 0.0001(8) 0.0000(9) -0.0039(10) C20 0.0455(16) 0.0211(11) 0.0103(10) 0.0006(8) 0.0021(9) -0.0003(10) C21 0.0513(17) 0.0203(11) 0.0126(10) -0.0030(8) 0.0006(10) -0.0029(11) O5 0.0855(16) 0.0211(9) 0.0111(7) -0.0020(6) 0.0066(9) 0.0037(9) C22 0.0570(19) 0.0248(12) 0.0095(10) 0.0006(8) 0.0006(10) -0.0031(12) C23 0.0580(18) 0.0202(11) 0.0104(10) 0.0033(8) 0.0003(10) -0.0003(11) O6 0.0580(18) 0.0202(11) 0.0104(10) 0.0033(8) 0.0003(10) -0.0003(11) C24 0.0462(16) 0.0215(11) 0.0113(10) -0.0008(8) 0.0011(10) 0.0002(11) C25 0.0381(15) 0.0214(11) 0.0083(9) 0.0000(8) 0.0015(9) 0.0008(10) C26 0.0448(16) 0.0180(11) 0.0117(10) 0.0021(8) 0.0025(9) -0.0045(10) C27 0.0440(16) 0.0187(11) 0.0120(10) -0.0017(8) -0.0009(9) -0.0024(10) C28 0.0329(15) 0.0204(11) 0.0284(13) 0.0031(9) 0.0048(10) 0.0000(10) C29 0.0312(15) 0.0225(12) 0.0254(12) 0.0009(9) 0.0046(10) -0.0006(10) C30 0.0347(15) 0.0205(11) 0.0277(13) 0.0009(9) 0.0000(10) -0.0024(10) O7 0.0338(11) 0.0524(13) 0.0265(10) -0.0025(9) 0.0028(8) -0.0054(9) C31 0.0291(14) 0.0246(12) 0.0313(13) 0.0016(10) 0.0080(10) -0.0019(10) C32 0.0415(17) 0.0205(12) 0.0234(12) 0.0009(9) 0.0070(11) 0.0010(11) O8 0.0395(12) 0.0486(12) 0.0245(9) 0.0003(8) 0.0056(8) 0.0004(10) C33 0.0351(15) 0.0232(12) 0.0257(12) 0.0004(9) 0.0013(10) 0.0006(10) C34 0.0314(15) 0.0282(13) 0.0270(12) 0.0004(10) 0.0038(10) 0.0012(11) C35 0.0354(16) 0.0348(14) 0.0335(14) 0.0114(11) 0.0016(11) 0.0037(12) C36 0.0393(17) 0.0338(14) 0.0315(14) 0.0115(11) 0.0059(12) -0.0005(12) C37 0.020(3) 0.071(5) 0.072(5) 0.012(4) -0.002(3) 0.004(3) C38 0.075(6) 0.052(4) 0.057(4) -0.006(3) -0.012(4) 0.000(4) O9 0.016(2) 0.125(5) 0.077(4) -0.035(4) 0.006(2) -0.013(3) O10 0.045(3) 0.060(3) 0.091(4) 0.007(3) 0.014(3) 0.004(2) C39 0.055(5) 0.048(5) 0.137(9) -0.019(5) -0.036(5) 0.013(4) C40 0.055(5) 0.048(5) 0.137(9) -0.019(5) -0.036(5) 0.013(4) O11 0.0678(16) 0.0333(11) 0.0264(10) -0.0017(8) 0.0011(10) 0.0023(11) O12 0.0508(14) 0.0266(10) 0.0271(10) -0.0011(7) 0.0101(9) 0.0011(9) O14 0.0501(13) 0.0307(10) 0.0276(10) -0.0008(8) 0.0052(9) -0.0008(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 C2 1.397(3) . ? C1 C6 1.399(3) . ? C1 C7 1.487(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 O1 1.382(3) . ? O1 H1 0.8400 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 O2 1.378(3) . ? C5 C6 1.382(3) . ? O2 H2A 0.8400 . ? C6 H6 0.9500 . ? C7 C12 1.397(3) . ? C7 C8 1.397(3) . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.395(3) . ? C9 H9 0.9500 . ? C10 C11 1.389(3) . ? C10 C13 1.488(3) . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.392(3) . ? C13 C14 1.394(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 O3 1.378(3) . ? C15 C16 1.380(3) . ? O3 H3 0.8400 . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 O4 1.374(3) . ? C17 C18 1.390(3) . ? O4 H4A 0.8400 . ? C18 H18 0.9500 . ? C19 C20 1.393(3) . ? C19 C24 1.399(3) . ? C19 C25 1.484(3) . ? C20 C21 1.390(3) . ? C20 H20 0.9500 . ? C21 O5 1.371(3) . ? C21 C22 1.390(3) . ? O5 H5 0.8400 . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 O6 1.372(3) . ? C23 C24 1.383(3) . ? O6 H6A 0.8400 . ? C24 H24 0.9500 . ? C25 C26 1.394(3) . ? C25 C27 1.395(3) . ? C26 C27 1.392(3) 3_556 ? C26 H26 0.9500 . ? C27 C26 1.392(3) 3_556 ? C27 H27 0.9500 . ? C28 C29 1.393(4) . ? C28 C33 1.400(3) . ? C28 C34 1.479(4) . ? C29 C30 1.389(4) . ? C29 H29 0.9500 . ? C30 O7 1.372(3) . ? C30 C31 1.381(4) . ? O7 H7 0.8400 . ? C31 C32 1.386(4) . ? C31 H31 0.9500 . ? C32 O8 1.376(3) . ? C32 C33 1.377(4) . ? O8 H8A 0.8400 . ? C33 H33 0.9500 . ? C34 C36 1.396(4) . ? C34 C35 1.399(4) . ? C35 C36 1.365(4) 3_666 ? C35 H35 0.9500 . ? C36 C35 1.365(4) 3_666 ? C36 H36 0.9500 . ? C37 C38 1.469(10) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 O9 1.224(10) . ? C38 O10 1.315(10) . ? O10 C39 1.477(10) . ? C39 C40 1.395(13) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? O11 H11A 0.845(18) . ? O11 H11B 0.827(18) . ? O12 H12A 0.857(17) . ? O12 H12B 0.871(17) . ? O14 H14A 0.874(18) . ? O14 H14B 0.858(18) . ? 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 C6 118.9(2) . . ? C2 C1 C7 120.6(2) . . ? C6 C1 C7 120.4(2) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.7(2) . . ? C2 C3 O1 117.2(2) . . ? C4 C3 O1 121.1(2) . . ? C3 O1 H1 109.5 . . ? C3 C4 C5 118.1(2) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? O2 C5 C6 121.8(2) . . ? O2 C5 C4 116.7(2) . . ? C6 C5 C4 121.6(2) . . ? C5 O2 H2A 109.5 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 118.0(2) . . ? C12 C7 C1 121.2(2) . . ? C8 C7 C1 120.8(2) . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 121.3(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 117.9(2) . . ? C11 C10 C13 121.6(2) . . ? C9 C10 C13 120.5(2) . . ? C10 C11 C12 121.2(2) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C7 120.8(2) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C18 C13 C14 119.3(2) . . ? C18 C13 C10 120.6(2) . . ? C14 C13 C10 120.1(2) . . ? C15 C14 C13 119.8(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? O3 C15 C16 117.2(2) . . ? O3 C15 C14 121.4(2) . . ? C16 C15 C14 121.4(2) . . ? C15 O3 H3 109.5 . . ? C15 C16 C17 118.5(2) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? O4 C17 C16 121.4(2) . . ? O4 C17 C18 117.3(2) . . ? C16 C17 C18 121.3(2) . . ? C17 O4 H4A 109.5 . . ? C17 C18 C13 119.7(2) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? C20 C19 C24 119.1(2) . . ? C20 C19 C25 120.0(2) . . ? C24 C19 C25 120.9(2) . . ? C21 C20 C19 119.8(2) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? O5 C21 C20 117.4(2) . . ? O5 C21 C22 121.2(2) . . ? C20 C21 C22 121.4(2) . . ? C21 O5 H5 109.5 . . ? C23 C22 C21 118.2(2) . . ? C23 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? O6 C23 C24 122.6(2) . . ? O6 C23 C22 116.0(2) . . ? C24 C23 C22 121.4(2) . . ? C23 O6 H6A 109.5 . . ? C23 C24 C19 120.1(2) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? C26 C25 C27 117.5(2) . . ? C26 C25 C19 121.5(2) . . ? C27 C25 C19 121.0(2) . . ? C27 C26 C25 121.1(2) 3_556 . ? C27 C26 H26 119.4 3_556 . ? C25 C26 H26 119.4 . . ? C26 C27 C25 121.4(2) 3_556 . ? C26 C27 H27 119.3 3_556 . ? C25 C27 H27 119.3 . . ? C29 C28 C33 119.8(3) . . ? C29 C28 C34 120.1(2) . . ? C33 C28 C34 120.2(2) . . ? C30 C29 C28 119.3(2) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? O7 C30 C31 117.0(2) . . ? O7 C30 C29 121.2(2) . . ? C31 C30 C29 121.8(3) . . ? C30 O7 H7 109.5 . . ? C30 C31 C32 117.8(3) . . ? C30 C31 H31 121.1 . . ? C32 C31 H31 121.1 . . ? O8 C32 C33 121.0(2) . . ? O8 C32 C31 116.6(3) . . ? C33 C32 C31 122.3(2) . . ? C32 O8 H8A 109.5 . . ? C32 C33 C28 119.0(3) . . ? C32 C33 H33 120.5 . . ? C28 C33 H33 120.5 . . ? C36 C34 C35 117.2(3) . . ? C36 C34 C28 121.1(2) . . ? C35 C34 C28 121.8(2) . . ? C36 C35 C34 121.5(3) 3_666 . ? C36 C35 H35 119.2 3_666 . ? C34 C35 H35 119.2 . . ? C35 C36 C34 121.3(3) 3_666 . ? C35 C36 H36 119.4 3_666 . ? C34 C36 H36 119.4 . . ? C38 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O9 C38 O10 128.5(8) . . ? O9 C38 C37 121.0(8) . . ? O10 C38 C37 110.5(7) . . ? C38 O10 C39 119.3(7) . . ? C40 C39 O10 107.9(7) . . ? C40 C39 H39A 110.1 . . ? O10 C39 H39A 110.1 . . ? C40 C39 H39B 110.1 . . ? O10 C39 H39B 110.1 . . ? H39A C39 H39B 108.4 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? H11A O11 H11B 131(4) . . ? H12A O12 H12B 121(3) . . ? H14A O14 H14B 121(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.645 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.119 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 -0.015 0.250 227 40 ' ' 2 0.500 -0.008 0.750 227 40 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934375' ####################################################################### # # 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_e2216a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H36 O8' _chemical_formula_sum 'C49 H36 O8' _chemical_formula_weight 752.78 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.8482(13) _cell_length_b 7.0555(2) _cell_length_c 25.7963(18) _cell_angle_alpha 90.00 _cell_angle_beta 128.8150(10) _cell_angle_gamma 90.00 _cell_volume 4658.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4514 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.87 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.073 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9949 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details sadabs _exptl_special_details ; The disordered solvent molecules could not be refined. The SQUEEZE command was therefore applied. ; _diffrn_ambient_temperature 173(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 21732 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5685 _reflns_number_gt 3812 _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^)+(0.1124P)^2^+0.3230P] 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 5685 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.0000 0.3203(3) 0.2500 0.0214(5) Uani 1 2 d S . . C2 C 0.03455(6) 0.1888(2) 0.31088(8) 0.0225(4) Uani 1 1 d . . . C3 C 0.01062(6) 0.0519(2) 0.32311(9) 0.0266(4) Uani 1 1 d . . . H3 H -0.0263 0.0400 0.2928 0.032 Uiso 1 1 calc R . . C4 C 0.03910(7) -0.0664(3) 0.37783(9) 0.0280(4) Uani 1 1 d . . . H4 H 0.0214 -0.1552 0.3851 0.034 Uiso 1 1 calc R . . C5 C 0.09394(7) -0.0569(2) 0.42292(9) 0.0260(4) Uani 1 1 d . . . C6 C 0.11756(7) 0.0736(3) 0.40903(9) 0.0295(4) Uani 1 1 d . . . H6 H 0.1546 0.0806 0.4377 0.035 Uiso 1 1 calc R . . C7 C 0.08866(7) 0.1943(3) 0.35455(9) 0.0270(4) Uani 1 1 d . . . H7 H 0.1064 0.2825 0.3471 0.032 Uiso 1 1 calc R . . C8 C 0.12571(7) -0.1796(3) 0.48289(9) 0.0300(4) Uani 1 1 d . . . C9 C 0.10948(7) -0.3601(3) 0.48414(10) 0.0356(5) Uani 1 1 d . . . H9 H 0.0770 -0.4078 0.4461 0.043 Uiso 1 1 calc R . . C10 C 0.14083(8) -0.4714(3) 0.54118(11) 0.0405(5) Uani 1 1 d . . . O1 O 0.12519(7) -0.6488(2) 0.54225(9) 0.0644(5) Uani 1 1 d . . . H1 H 0.0925 -0.6560 0.5141 0.097 Uiso 1 1 calc R . . C11 C 0.18864(8) -0.4044(3) 0.59690(10) 0.0392(5) Uani 1 1 d . . . H11 H 0.2099 -0.4807 0.6357 0.047 Uiso 1 1 calc R . . C12 C 0.20470(7) -0.2266(3) 0.59518(10) 0.0352(5) Uani 1 1 d . . . O2 O 0.25128(6) -0.1499(2) 0.64863(7) 0.0500(4) Uani 1 1 d . . . H2 H 0.2702 -0.2358 0.6762 0.075 Uiso 1 1 calc R . . C13 C 0.17365(7) -0.1124(3) 0.53927(9) 0.0320(4) Uani 1 1 d . . . H13 H 0.1850 0.0115 0.5394 0.038 Uiso 1 1 calc R . . C14 C 0.03351(6) 0.4537(2) 0.24248(8) 0.0222(4) Uani 1 1 d . . . C15 C 0.03323(7) 0.4501(3) 0.18829(9) 0.0275(4) Uani 1 1 d . . . H15 H 0.0118 0.3612 0.1535 0.033 Uiso 1 1 calc R . . C16 C 0.06409(7) 0.5755(3) 0.18443(9) 0.0276(4) Uani 1 1 d . . . H16 H 0.0626 0.5721 0.1465 0.033 Uiso 1 1 calc R . . C17 C 0.09700(6) 0.7053(2) 0.23486(9) 0.0251(4) Uani 1 1 d . . . C18 C 0.09591(7) 0.7117(2) 0.28805(9) 0.0272(4) Uani 1 1 d . . . H18 H 0.1172 0.8012 0.3227 0.033 Uiso 1 1 calc R . . C19 C 0.06462(7) 0.5909(3) 0.29133(9) 0.0267(4) Uani 1 1 d . . . H19 H 0.0642 0.6010 0.3277 0.032 Uiso 1 1 calc R . . C20 C 0.13110(6) 0.8339(2) 0.23123(9) 0.0262(4) Uani 1 1 d . . . C21 C 0.15068(7) 0.7750(3) 0.19876(9) 0.0264(4) Uani 1 1 d . . . H21 H 0.1422 0.6528 0.1790 0.032 Uiso 1 1 calc R . . C22 C 0.18229(6) 0.8948(3) 0.19554(9) 0.0272(4) Uani 1 1 d . . . O3 O 0.20052(5) 0.83354(19) 0.16264(7) 0.0369(4) Uani 1 1 d . . . H3A H 0.2131 0.9258 0.1563 0.055 Uiso 1 1 calc R . . C23 C 0.19599(8) 1.0720(3) 0.22465(11) 0.0354(5) Uani 1 1 d . . . H23 H 0.2181 1.1525 0.2226 0.043 Uiso 1 1 calc R . . C24 C 0.17690(9) 1.1295(3) 0.25672(12) 0.0445(5) Uani 1 1 d . . . O4 O 0.18893(9) 1.3066(2) 0.28366(15) 0.0445(5) Uani 1 1 d . . . H4A H 0.2206 1.3290 0.3032 0.057 Uiso 1 1 calc R . . C25 C 0.14474(8) 1.0117(3) 0.26038(11) 0.0378(5) Uani 1 1 d . . . H25 H 0.1321 1.0535 0.2830 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0217(11) 0.0210(12) 0.0187(11) 0.000 0.0113(10) 0.000 C2 0.0224(8) 0.0213(9) 0.0200(8) 0.0005(7) 0.0115(7) 0.0020(6) C3 0.0206(8) 0.0249(10) 0.0256(9) -0.0003(7) 0.0102(7) -0.0034(7) C4 0.0284(9) 0.0240(10) 0.0277(9) -0.0001(7) 0.0157(8) -0.0046(7) C5 0.0267(8) 0.0227(9) 0.0235(8) 0.0005(7) 0.0133(7) 0.0013(7) C6 0.0208(8) 0.0334(11) 0.0258(9) 0.0036(8) 0.0104(7) 0.0006(7) C7 0.0243(8) 0.0290(10) 0.0274(9) 0.0019(7) 0.0161(8) -0.0012(7) C8 0.0294(9) 0.0293(10) 0.0266(9) 0.0036(8) 0.0153(8) 0.0036(7) C9 0.0324(10) 0.0342(11) 0.0270(9) 0.0033(8) 0.0122(8) -0.0015(8) C10 0.0440(12) 0.0309(11) 0.0381(11) 0.0083(9) 0.0215(10) 0.0005(9) O1 0.0563(10) 0.0402(10) 0.0607(12) 0.0185(8) 0.0192(9) -0.0071(8) C11 0.0424(11) 0.0355(12) 0.0312(10) 0.0112(9) 0.0189(9) 0.0087(9) C12 0.0281(9) 0.0415(12) 0.0260(10) 0.0008(8) 0.0121(8) 0.0023(8) O2 0.0361(8) 0.0542(10) 0.0300(8) 0.0059(7) 0.0063(7) -0.0002(7) C13 0.0301(9) 0.0296(10) 0.0263(9) 0.0024(8) 0.0129(8) 0.0011(8) C14 0.0216(8) 0.0195(9) 0.0243(8) 0.0015(7) 0.0137(7) 0.0013(6) C15 0.0269(9) 0.0297(10) 0.0240(9) -0.0040(7) 0.0151(8) -0.0036(7) C16 0.0301(9) 0.0297(10) 0.0268(9) -0.0036(7) 0.0198(8) -0.0040(7) C17 0.0245(8) 0.0226(9) 0.0266(9) 0.0024(7) 0.0153(8) 0.0029(7) C18 0.0296(9) 0.0222(9) 0.0294(9) -0.0042(7) 0.0183(8) -0.0023(7) C19 0.0337(9) 0.0247(10) 0.0253(9) -0.0038(7) 0.0202(8) -0.0021(7) C20 0.0247(8) 0.0246(9) 0.0275(9) 0.0020(7) 0.0155(7) 0.0019(7) C21 0.0279(9) 0.0251(10) 0.0256(9) -0.0012(7) 0.0166(8) -0.0007(7) C22 0.0259(9) 0.0283(10) 0.0269(9) 0.0014(7) 0.0163(8) 0.0018(7) O3 0.0400(8) 0.0397(8) 0.0428(8) -0.0068(7) 0.0317(7) -0.0082(6) C23 0.0389(10) 0.0301(11) 0.0456(12) -0.0023(9) 0.0305(10) -0.0055(8) C24 0.0587(13) 0.0274(11) 0.0635(15) -0.0113(10) 0.0461(13) -0.0097(9) O4 0.0587(13) 0.0274(11) 0.0635(15) -0.0113(10) 0.0461(13) -0.0097(9) C25 0.0492(12) 0.0275(11) 0.0546(13) -0.0074(9) 0.0412(11) -0.0041(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 C2 1.543(2) 2 ? C1 C2 1.543(2) . ? C1 C14 1.550(2) 2 ? C1 C14 1.550(2) . ? C2 C7 1.386(2) . ? C2 C3 1.400(2) . ? C3 C4 1.382(2) . ? C3 H3 0.9500 . ? C4 C5 1.406(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(3) . ? C5 C8 1.486(2) . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.389(3) . ? C8 C13 1.396(3) . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 O1 1.360(3) . ? C10 C11 1.388(3) . ? O1 H1 0.8400 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 O2 1.375(2) . ? C12 C13 1.388(3) . ? O2 H2 0.8400 . ? C13 H13 0.9500 . ? C14 C15 1.392(2) . ? C14 C19 1.398(2) . ? C15 C16 1.395(2) . ? C15 H15 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 C20 1.489(2) . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.384(3) . ? C20 C21 1.402(2) . ? C21 C22 1.381(2) . ? C21 H21 0.9500 . ? C22 O3 1.379(2) . ? C22 C23 1.381(3) . ? O3 H3A 0.8400 . ? C23 C24 1.376(3) . ? C23 H23 0.9500 . ? C24 O4 1.362(3) . ? C24 C25 1.393(3) . ? O4 H4A 0.8400 . ? C25 H25 0.9500 . ? 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 C2 106.06(18) 2 . ? C2 C1 C14 111.45(8) 2 2 ? C2 C1 C14 111.40(9) . 2 ? C2 C1 C14 111.40(9) 2 . ? C2 C1 C14 111.45(8) . . ? C14 C1 C14 105.19(18) 2 . ? C7 C2 C3 116.84(15) . . ? C7 C2 C1 124.11(14) . . ? C3 C2 C1 119.04(13) . . ? C4 C3 C2 122.05(15) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 120.84(16) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 116.84(16) . . ? C6 C5 C8 120.92(16) . . ? C4 C5 C8 122.24(16) . . ? C5 C6 C7 122.01(16) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C2 C7 C6 121.34(16) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C9 C8 C13 119.08(17) . . ? C9 C8 C5 121.95(17) . . ? C13 C8 C5 118.97(16) . . ? C8 C9 C10 120.04(18) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? O1 C10 C11 119.26(18) . . ? O1 C10 C9 120.08(19) . . ? C11 C10 C9 120.64(19) . . ? C10 O1 H1 109.5 . . ? C12 C11 C10 119.07(18) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 O2 122.42(18) . . ? C11 C12 C13 121.16(18) . . ? O2 C12 C13 116.40(18) . . ? C12 O2 H2 109.5 . . ? C12 C13 C8 119.98(18) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C15 C14 C19 117.32(15) . . ? C15 C14 C1 123.78(14) . . ? C19 C14 C1 118.86(14) . . ? C14 C15 C16 120.81(16) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 121.60(16) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 117.17(16) . . ? C16 C17 C20 121.10(16) . . ? C18 C17 C20 121.73(16) . . ? C19 C18 C17 121.34(17) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C14 121.64(16) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? C25 C20 C21 118.71(16) . . ? C25 C20 C17 121.18(16) . . ? C21 C20 C17 120.10(16) . . ? C22 C21 C20 119.87(17) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? O3 C22 C23 119.94(16) . . ? O3 C22 C21 118.54(16) . . ? C23 C22 C21 121.52(17) . . ? C22 O3 H3A 109.5 . . ? C24 C23 C22 118.56(18) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? O4 C24 C23 118.77(19) . . ? O4 C24 C25 120.2(2) . . ? C23 C24 C25 121.04(19) . . ? C24 O4 H4A 109.5 . . ? C20 C25 C24 120.30(18) . . ? C20 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.288 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.064 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 -0.013 0.000 177.5 33.7 2 0.000 -0.016 0.500 177.5 33.7 3 0.250 -0.017 0.500 158.5 28.6 4 0.250 -0.057 1.000 158.5 28.6 5 0.500 -0.066 0.500 177.5 33.7 6 0.500 -0.028 1.000 177.5 33.7 7 0.750 -0.053 0.500 158.5 28.6 8 0.750 -0.014 1.000 158.5 28.6 _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934376' ####################################################################### # # 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_e2366b #TrackingRef 's2366.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8893(2) _cell_length_b 9.9296(2) _cell_length_c 11.9272(3) _cell_angle_alpha 74.7250(10) _cell_angle_beta 81.3570(10) _cell_angle_gamma 83.1840(10) _cell_volume 888.04(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5083 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.07 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9894 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 12010 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 29.11 _reflns_number_total 4728 _reflns_number_gt 3789 _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^)+(0.0616P)^2^+0.2153P] 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 4728 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.13658(15) 0.77135(11) 0.54257(10) 0.0253(2) Uani 1 1 d . . . C2 C -0.00356(16) 0.77576(12) 0.48151(10) 0.0269(2) Uani 1 1 d . . . H2 H -0.0873 0.7096 0.5109 0.032 Uiso 1 1 calc R . . C3 C -0.01860(16) 0.87759(12) 0.37795(10) 0.0275(2) Uani 1 1 d . . . C4 C 0.10508(16) 0.97360(12) 0.33170(10) 0.0283(3) Uani 1 1 d . . . H4 H 0.0953 1.0411 0.2594 0.034 Uiso 1 1 calc R . . C5 C 0.24202(15) 0.96869(11) 0.39297(10) 0.0266(2) Uani 1 1 d . . . C6 C 0.25920(16) 0.86746(12) 0.49802(10) 0.0269(2) Uani 1 1 d . . . H6 H 0.3547 0.8644 0.5389 0.032 Uiso 1 1 calc R . . O1 O -0.15406(12) 0.89536(10) 0.31449(8) 0.0361(2) Uani 1 1 d . . . C7 C -0.30109(17) 0.82252(14) 0.37071(12) 0.0349(3) Uani 1 1 d . . . H7A H -0.2729 0.7217 0.3801 0.052 Uiso 1 1 calc R . . H7B H -0.3958 0.8543 0.3229 0.052 Uiso 1 1 calc R . . H7C H -0.3357 0.8415 0.4478 0.052 Uiso 1 1 calc R . . O2 O 0.36650(12) 1.06137(9) 0.35813(8) 0.0333(2) Uani 1 1 d . . . C8 C 0.34764(19) 1.17191(13) 0.25500(12) 0.0365(3) Uani 1 1 d . . . H8A H 0.3530 1.1320 0.1875 0.055 Uiso 1 1 calc R . . H8B H 0.4406 1.2338 0.2418 0.055 Uiso 1 1 calc R . . H8C H 0.2364 1.2257 0.2650 0.055 Uiso 1 1 calc R . . C9 C 0.14498(15) 0.66849(11) 0.65769(10) 0.0255(2) Uani 1 1 d . . . C10 C 0.19974(15) 0.70713(11) 0.75010(10) 0.0259(2) Uani 1 1 d . . . H10 H 0.2368 0.7982 0.7369 0.031 Uiso 1 1 calc R . . C11 C 0.20152(15) 0.61557(11) 0.86125(10) 0.0257(2) Uani 1 1 d . . . C12 C 0.14806(16) 0.48128(12) 0.87789(10) 0.0294(3) Uani 1 1 d . . . H12 H 0.1479 0.4170 0.9527 0.035 Uiso 1 1 calc R . . C13 C 0.09553(17) 0.44104(12) 0.78684(11) 0.0312(3) Uani 1 1 d . . . H13 H 0.0610 0.3492 0.7994 0.037 Uiso 1 1 calc R . . C14 C 0.09290(16) 0.53344(12) 0.67760(11) 0.0289(3) Uani 1 1 d . . . H14 H 0.0556 0.5051 0.6159 0.035 Uiso 1 1 calc R . . C15 C 0.25145(15) 0.66006(11) 0.96068(10) 0.0259(2) Uani 1 1 d . . . C16 C 0.30313(16) 0.56164(12) 1.05816(10) 0.0287(2) Uani 1 1 d . . . H16 H 0.3146 0.4650 1.0593 0.034 Uiso 1 1 calc R . . C17 C 0.33840(16) 0.60320(12) 1.15442(10) 0.0284(2) Uani 1 1 d . . . C18 C 0.32912(17) 0.74340(12) 1.15325(10) 0.0310(3) Uani 1 1 d . . . H18 H 0.3539 0.7716 1.2188 0.037 Uiso 1 1 calc R . . C19 C 0.28255(18) 0.84252(12) 1.05348(11) 0.0316(3) Uani 1 1 d . . . C20 C 0.24103(17) 0.80331(12) 0.95861(10) 0.0295(3) Uani 1 1 d . . . H20 H 0.2058 0.8724 0.8926 0.035 Uiso 1 1 calc R . . O3 O 0.37974(13) 0.49609(9) 1.24748(8) 0.0378(2) Uani 1 1 d . . . C21 C 0.4162(2) 0.53066(15) 1.34847(12) 0.0419(3) Uani 1 1 d . . . H21A H 0.5161 0.5862 1.3282 0.063 Uiso 1 1 calc R . . H21B H 0.4412 0.4445 1.4083 0.063 Uiso 1 1 calc R . . H21C H 0.3165 0.5852 1.3789 0.063 Uiso 1 1 calc R . . O4 O 0.27891(16) 0.97847(9) 1.05975(8) 0.0460(3) Uani 1 1 d . . . C22 C 0.2516(3) 1.08550(14) 0.95650(13) 0.0518(4) Uani 1 1 d . . . H22A H 0.3376 1.0701 0.8917 0.078 Uiso 1 1 calc R . . H22B H 0.2623 1.1771 0.9701 0.078 Uiso 1 1 calc R . . H22C H 0.1362 1.0830 0.9366 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0262(6) 0.0225(5) 0.0281(5) -0.0100(4) -0.0012(4) -0.0002(4) C2 0.0261(6) 0.0256(5) 0.0308(5) -0.0106(4) -0.0015(4) -0.0044(4) C3 0.0259(6) 0.0296(6) 0.0298(5) -0.0123(4) -0.0042(4) -0.0015(4) C4 0.0291(7) 0.0270(5) 0.0291(5) -0.0084(4) -0.0025(4) -0.0017(4) C5 0.0252(6) 0.0238(5) 0.0316(6) -0.0103(4) 0.0007(4) -0.0031(4) C6 0.0247(6) 0.0269(5) 0.0307(5) -0.0102(4) -0.0034(4) -0.0013(4) O1 0.0302(5) 0.0437(5) 0.0357(5) -0.0065(4) -0.0098(4) -0.0091(4) C7 0.0262(7) 0.0396(7) 0.0418(7) -0.0133(5) -0.0063(5) -0.0047(5) O2 0.0305(5) 0.0303(4) 0.0384(5) -0.0041(4) -0.0045(4) -0.0092(3) C8 0.0389(8) 0.0298(6) 0.0388(7) -0.0034(5) -0.0021(5) -0.0097(5) C9 0.0228(6) 0.0235(5) 0.0302(5) -0.0087(4) -0.0009(4) -0.0006(4) C10 0.0248(6) 0.0231(5) 0.0306(5) -0.0082(4) -0.0018(4) -0.0030(4) C11 0.0244(6) 0.0234(5) 0.0299(5) -0.0095(4) -0.0005(4) -0.0014(4) C12 0.0332(7) 0.0232(5) 0.0307(6) -0.0068(4) 0.0003(5) -0.0034(4) C13 0.0349(7) 0.0232(5) 0.0369(6) -0.0105(5) -0.0005(5) -0.0058(4) C14 0.0297(7) 0.0257(5) 0.0339(6) -0.0123(4) -0.0030(5) -0.0026(4) C15 0.0254(6) 0.0241(5) 0.0284(5) -0.0082(4) 0.0003(4) -0.0033(4) C16 0.0299(7) 0.0218(5) 0.0342(6) -0.0073(4) -0.0036(5) -0.0016(4) C17 0.0271(7) 0.0251(5) 0.0319(6) -0.0041(4) -0.0051(5) -0.0022(4) C18 0.0367(7) 0.0276(6) 0.0304(6) -0.0084(5) -0.0062(5) -0.0038(5) C19 0.0403(8) 0.0224(5) 0.0326(6) -0.0082(4) -0.0038(5) -0.0029(5) C20 0.0362(7) 0.0224(5) 0.0290(5) -0.0058(4) -0.0036(5) -0.0011(4) O3 0.0500(6) 0.0271(4) 0.0370(5) -0.0041(4) -0.0165(4) -0.0012(4) C21 0.0529(10) 0.0375(7) 0.0368(7) -0.0048(5) -0.0170(6) -0.0053(6) O4 0.0845(8) 0.0212(4) 0.0355(5) -0.0080(4) -0.0163(5) -0.0032(4) C22 0.0902(13) 0.0237(6) 0.0436(8) -0.0051(5) -0.0216(8) -0.0036(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 C6 1.3879(16) . ? C1 C2 1.4030(17) . ? C1 C9 1.4850(15) . ? C2 C3 1.3855(16) . ? C2 H2 0.9500 . ? C3 O1 1.3690(15) . ? C3 C4 1.3955(17) . ? C4 C5 1.3818(18) . ? C4 H4 0.9500 . ? C5 O2 1.3691(14) . ? C5 C6 1.3977(16) . ? C6 H6 0.9500 . ? O1 C7 1.4241(15) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O2 C8 1.4300(15) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.3978(16) . ? C9 C14 1.3990(15) . ? C10 C11 1.3971(15) . ? C10 H10 0.9500 . ? C11 C12 1.4015(15) . ? C11 C15 1.4881(16) . ? C12 C13 1.3834(17) . ? C12 H12 0.9500 . ? C13 C14 1.3833(17) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.3865(16) . ? C15 C20 1.4089(15) . ? C16 C17 1.3924(17) . ? C16 H16 0.9500 . ? C17 O3 1.3689(14) . ? C17 C18 1.3818(16) . ? C18 C19 1.3958(17) . ? C18 H18 0.9500 . ? C19 O4 1.3682(14) . ? C19 C20 1.3831(17) . ? C20 H20 0.9500 . ? O3 C21 1.4130(16) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O4 C22 1.4241(16) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.80(11) . . ? C6 C1 C9 121.19(11) . . ? C2 C1 C9 118.91(10) . . ? C3 C2 C1 119.31(11) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? O1 C3 C2 124.06(11) . . ? O1 C3 C4 114.61(11) . . ? C2 C3 C4 121.31(11) . . ? C5 C4 C3 118.81(11) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? O2 C5 C4 123.62(10) . . ? O2 C5 C6 115.53(11) . . ? C4 C5 C6 120.84(11) . . ? C1 C6 C5 119.89(11) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C3 O1 C7 116.55(10) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 O2 C8 117.24(10) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.59(10) . . ? C10 C9 C1 120.17(10) . . ? C14 C9 C1 121.21(10) . . ? C11 C10 C9 121.86(10) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 117.89(10) . . ? C10 C11 C15 121.48(10) . . ? C12 C11 C15 120.59(10) . . ? C13 C12 C11 120.87(11) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.52(10) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 120.26(11) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C16 C15 C20 119.02(11) . . ? C16 C15 C11 120.75(10) . . ? C20 C15 C11 120.19(10) . . ? C15 C16 C17 120.60(10) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? O3 C17 C18 124.03(11) . . ? O3 C17 C16 115.11(10) . . ? C18 C17 C16 120.86(11) . . ? C17 C18 C19 118.43(11) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? O4 C19 C20 124.10(11) . . ? O4 C19 C18 114.28(11) . . ? C20 C19 C18 121.61(10) . . ? C19 C20 C15 119.41(11) . . ? C19 C20 H20 120.3 . . ? C15 C20 H20 120.3 . . ? C17 O3 C21 118.15(10) . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 O4 C22 117.39(10) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.330 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 934377' ####################################################################### # # 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_e2491a #TrackingRef 's2491.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 O6,2(C3 H6 O),H2 O' _chemical_formula_sum 'C30 H32 O9' _chemical_formula_weight 536.56 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)/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 12.0986(4) _cell_length_b 20.2849(5) _cell_length_c 11.2091(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.4490(10) _cell_angle_gamma 90.00 _cell_volume 2721.07(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5376 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 29.23 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9942 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 22721 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 29.08 _reflns_number_total 6951 _reflns_number_gt 4847 _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^)+(0.0763P)^2^+0.4131P] 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 6951 _refine_ls_number_parameters 368 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.003 _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 0.83552(13) 0.48880(8) 0.88576(12) 0.0200(3) Uani 1 1 d . . . H1 H 0.8632 0.5309 0.8681 0.024 Uiso 1 1 calc R . . C2 C 0.90531(12) 0.43399(8) 0.89789(12) 0.0195(3) Uani 1 1 d . . . O1 O 1.01543(9) 0.43909(6) 0.88290(11) 0.0286(3) Uani 1 1 d . . . H1A H 1.0238 0.4719 0.8393 0.043 Uiso 1 1 calc R . . C3 C 0.86638(13) 0.37249(8) 0.92578(13) 0.0199(3) Uani 1 1 d . . . H3 H 0.9152 0.3356 0.9334 0.024 Uiso 1 1 calc R . . C4 C 0.75510(12) 0.36512(7) 0.94254(12) 0.0171(3) Uani 1 1 d . . . C5 C 0.68432(13) 0.41967(7) 0.92964(12) 0.0188(3) Uani 1 1 d . . . H5 H 0.6084 0.4151 0.9411 0.023 Uiso 1 1 calc R . . C6 C 0.72458(13) 0.48045(8) 0.90009(13) 0.0197(3) Uani 1 1 d . . . O2 O 0.65610(10) 0.53491(5) 0.88364(11) 0.0284(3) Uani 1 1 d . . . H2 H 0.5892 0.5227 0.8676 0.043 Uiso 1 1 calc R . . C7 C 0.70912(12) 0.30006(7) 0.97052(12) 0.0177(3) Uani 1 1 d . . . C8 C 0.73288(12) 0.24281(7) 0.91036(12) 0.0188(3) Uani 1 1 d . . . H8 H 0.7853 0.2444 0.8551 0.023 Uiso 1 1 calc R . . C9 C 0.68093(12) 0.18338(7) 0.93003(12) 0.0173(3) Uani 1 1 d . . . C10 C 0.60413(12) 0.18151(7) 1.01163(12) 0.0178(3) Uani 1 1 d . . . H10 H 0.5679 0.1412 1.0247 0.021 Uiso 1 1 calc R . . C11 C 0.57972(12) 0.23787(7) 1.07429(11) 0.0165(3) Uani 1 1 d . . . C12 C 0.63402(12) 0.29641(7) 1.05326(12) 0.0178(3) Uani 1 1 d . . . H12 H 0.6194 0.3349 1.0966 0.021 Uiso 1 1 calc R . . C13 C 0.70470(13) 0.12381(7) 0.86031(12) 0.0178(3) Uani 1 1 d . . . C14 C 0.61812(13) 0.08241(7) 0.80952(12) 0.0189(3) Uani 1 1 d . . . H14 H 0.5432 0.0915 0.8203 0.023 Uiso 1 1 calc R . . C15 C 0.64249(13) 0.02797(7) 0.74319(13) 0.0199(3) Uani 1 1 d . . . O3 O 0.55509(9) -0.01112(6) 0.69277(11) 0.0283(3) Uani 1 1 d . . . H3A H 0.5803 -0.0457 0.6655 0.042 Uiso 1 1 calc R . . C16 C 0.75098(13) 0.01318(8) 0.72720(13) 0.0227(3) Uani 1 1 d . . . H16 H 0.7665 -0.0242 0.6814 0.027 Uiso 1 1 calc R . . C17 C 0.83669(13) 0.05402(8) 0.77935(14) 0.0248(3) Uani 1 1 d . . . O4 O 0.94285(10) 0.03770(7) 0.76196(13) 0.0409(4) Uani 1 1 d . . . H4 H 0.9890 0.0560 0.8149 0.061 Uiso 1 1 calc R . . C18 C 0.81444(13) 0.10913(8) 0.84536(13) 0.0225(3) Uani 1 1 d . . . H18 H 0.8739 0.1368 0.8803 0.027 Uiso 1 1 calc R . . C19 C 0.49477(12) 0.23844(7) 1.15760(11) 0.0162(3) Uani 1 1 d . . . C20 C 0.42890(13) 0.29444(7) 1.16156(12) 0.0191(3) Uani 1 1 d . . . H20 H 0.4382 0.3309 1.1108 0.023 Uiso 1 1 calc R . . C21 C 0.34972(13) 0.29723(8) 1.23940(12) 0.0205(3) Uani 1 1 d . . . O5 O 0.28603(11) 0.35203(6) 1.24840(10) 0.0310(3) Uani 1 1 d . . . H5A H 0.3019 0.3808 1.1998 0.047 Uiso 1 1 calc R . . C22 C 0.33300(13) 0.24365(8) 1.31230(12) 0.0208(3) Uani 1 1 d . . . H22 H 0.2785 0.2454 1.3652 0.025 Uiso 1 1 calc R . . C23 C 0.39757(13) 0.18767(7) 1.30606(12) 0.0176(3) Uani 1 1 d . . . O6 O 0.38260(10) 0.13278(5) 1.37470(9) 0.0220(2) Uani 1 1 d . . . H6 H 0.3246 0.1375 1.4069 0.033 Uiso 1 1 calc R . . C24 C 0.47914(12) 0.18460(7) 1.23079(12) 0.0171(3) Uani 1 1 d . . . H24 H 0.5238 0.1462 1.2292 0.021 Uiso 1 1 calc R . . C25 C 0.27108(19) 0.11809(11) 1.03522(18) 0.0490(5) Uani 1 1 d . . . H25A H 0.2305 0.1581 1.0515 0.073 Uiso 1 1 calc R . . H25B H 0.3349 0.1299 0.9949 0.073 Uiso 1 1 calc R . . H25C H 0.2979 0.0956 1.1114 0.073 Uiso 1 1 calc R . . C26 C 0.19510(17) 0.07340(10) 0.95602(15) 0.0363(4) Uani 1 1 d . . . C27 C 0.2425(2) 0.01031(11) 0.91989(18) 0.0519(6) Uani 1 1 d . . . H27A H 0.1832 -0.0162 0.8740 0.078 Uiso 1 1 calc R . . H27B H 0.2752 -0.0140 0.9921 0.078 Uiso 1 1 calc R . . H27C H 0.3006 0.0194 0.8697 0.078 Uiso 1 1 calc R . . O7 O 0.09855(13) 0.08902(8) 0.92216(14) 0.0537(4) Uani 1 1 d . . . C28 C 0.0128(2) 0.29431(12) 0.2059(2) 0.0562(6) Uani 1 1 d . . . H28A H 0.0606 0.3316 0.1915 0.084 Uiso 1 1 calc R . . H28B H 0.0324 0.2792 0.2894 0.084 Uiso 1 1 calc R . . H28C H -0.0656 0.3081 0.1921 0.084 Uiso 1 1 calc R . . C29 C 0.02973(17) 0.23971(10) 0.12231(16) 0.0380(5) Uani 1 1 d . . . C30 C -0.0160(3) 0.17406(12) 0.1473(2) 0.0669(8) Uani 1 1 d . . . H30A H -0.0007 0.1427 0.0852 0.100 Uiso 1 1 calc R . . H30B H -0.0969 0.1775 0.1466 0.100 Uiso 1 1 calc R . . H30C H 0.0194 0.1586 0.2266 0.100 Uiso 1 1 calc R . . O8 O 0.07688(14) 0.24845(7) 0.03527(12) 0.0484(4) Uani 1 1 d . . . O9 O 0.19402(11) 0.14243(7) 0.46967(12) 0.0338(3) Uani 1 1 d D . . H9A H 0.1693(16) 0.1793(7) 0.4946(17) 0.036 Uiso 1 1 d D . . H9B H 0.1433(15) 0.1132(8) 0.4478(17) 0.036 Uiso 1 1 d 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 0.0202(8) 0.0142(9) 0.0258(7) 0.0020(5) 0.0036(5) -0.0033(6) C2 0.0155(7) 0.0209(9) 0.0227(6) 0.0017(5) 0.0044(5) -0.0027(6) O1 0.0169(6) 0.0240(7) 0.0465(7) 0.0117(5) 0.0099(5) -0.0011(5) C3 0.0195(8) 0.0158(9) 0.0251(7) 0.0015(5) 0.0059(5) 0.0015(6) C4 0.0197(8) 0.0150(8) 0.0174(6) -0.0006(5) 0.0051(5) -0.0035(6) C5 0.0164(7) 0.0178(9) 0.0230(7) -0.0017(5) 0.0059(5) -0.0018(6) C6 0.0191(8) 0.0150(9) 0.0247(7) 0.0007(5) 0.0019(5) 0.0007(6) O2 0.0205(6) 0.0141(7) 0.0509(7) 0.0057(5) 0.0067(5) 0.0017(5) C7 0.0177(7) 0.0164(9) 0.0194(6) 0.0003(5) 0.0040(5) -0.0009(6) C8 0.0176(7) 0.0194(9) 0.0208(6) 0.0001(5) 0.0076(5) 0.0002(6) C9 0.0179(7) 0.0140(8) 0.0207(6) -0.0008(5) 0.0050(5) 0.0016(6) C10 0.0181(7) 0.0133(8) 0.0231(7) 0.0005(5) 0.0069(5) -0.0010(6) C11 0.0171(7) 0.0148(8) 0.0184(6) 0.0011(5) 0.0055(5) 0.0000(6) C12 0.0208(8) 0.0135(8) 0.0197(6) -0.0013(5) 0.0057(5) 0.0001(6) C13 0.0207(8) 0.0135(8) 0.0208(6) 0.0005(5) 0.0079(5) 0.0005(6) C14 0.0170(7) 0.0158(9) 0.0249(7) 0.0002(5) 0.0066(5) 0.0016(6) C15 0.0206(8) 0.0139(9) 0.0252(7) -0.0016(5) 0.0030(5) -0.0016(6) O3 0.0185(6) 0.0189(7) 0.0466(7) -0.0135(5) 0.0016(5) -0.0006(5) C16 0.0220(8) 0.0183(9) 0.0286(7) -0.0090(6) 0.0061(6) 0.0012(6) C17 0.0171(8) 0.0256(10) 0.0330(8) -0.0077(6) 0.0084(6) 0.0015(6) O4 0.0182(6) 0.0443(9) 0.0618(9) -0.0328(6) 0.0117(6) -0.0016(6) C18 0.0202(8) 0.0191(9) 0.0295(7) -0.0073(6) 0.0081(6) -0.0038(6) C19 0.0157(7) 0.0163(8) 0.0173(6) -0.0024(5) 0.0047(5) -0.0019(6) C20 0.0220(8) 0.0158(8) 0.0206(6) 0.0027(5) 0.0066(5) -0.0002(6) C21 0.0234(8) 0.0166(9) 0.0229(7) 0.0005(5) 0.0077(5) 0.0037(6) O5 0.0386(7) 0.0205(7) 0.0392(6) 0.0090(5) 0.0237(5) 0.0124(5) C22 0.0227(8) 0.0202(9) 0.0214(7) -0.0003(5) 0.0100(5) 0.0008(6) C23 0.0206(8) 0.0143(9) 0.0185(6) -0.0002(5) 0.0054(5) -0.0034(6) O6 0.0272(6) 0.0157(6) 0.0263(5) 0.0033(4) 0.0141(4) 0.0000(4) C24 0.0180(7) 0.0140(8) 0.0203(6) -0.0013(5) 0.0058(5) -0.0003(6) C25 0.0493(14) 0.0486(14) 0.0437(11) -0.0022(9) -0.0106(9) -0.0091(10) C26 0.0415(12) 0.0388(12) 0.0280(8) 0.0026(7) 0.0031(7) -0.0078(9) C27 0.0768(18) 0.0409(14) 0.0347(10) 0.0050(8) -0.0027(10) 0.0065(11) O7 0.0345(9) 0.0652(11) 0.0595(9) -0.0206(7) 0.0002(7) -0.0079(7) C28 0.0650(17) 0.0579(16) 0.0489(12) -0.0113(10) 0.0188(11) 0.0031(12) C29 0.0412(12) 0.0415(13) 0.0322(9) 0.0041(7) 0.0089(7) 0.0025(9) C30 0.103(2) 0.0538(16) 0.0493(13) 0.0027(10) 0.0296(13) -0.0228(15) O8 0.0692(11) 0.0342(9) 0.0483(8) 0.0059(6) 0.0304(7) 0.0029(7) O9 0.0284(7) 0.0258(8) 0.0500(7) -0.0077(5) 0.0153(5) -0.0064(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 C6 1.385(2) . ? C1 C2 1.391(2) . ? C1 H1 0.9500 . ? C2 O1 1.3710(18) . ? C2 C3 1.385(2) . ? O1 H1A 0.8400 . ? C3 C4 1.394(2) . ? C3 H3 0.9500 . ? C4 C5 1.394(2) . ? C4 C7 1.484(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 O2 1.3769(19) . ? O2 H2 0.8400 . ? C7 C12 1.3924(19) . ? C7 C8 1.394(2) . ? C8 C9 1.392(2) . ? C8 H8 0.9500 . ? C9 C10 1.3968(19) . ? C9 C13 1.490(2) . ? C10 C11 1.396(2) . ? C10 H10 0.9500 . ? C11 C12 1.394(2) . ? C11 C19 1.4867(19) . ? C12 H12 0.9500 . ? C13 C18 1.395(2) . ? C13 C14 1.397(2) . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 O3 1.3751(18) . ? C15 C16 1.384(2) . ? O3 H3A 0.8400 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 O4 1.3677(19) . ? C17 C18 1.389(2) . ? O4 H4 0.8400 . ? C18 H18 0.9500 . ? C19 C20 1.392(2) . ? C19 C24 1.396(2) . ? C20 C21 1.389(2) . ? C20 H20 0.9500 . ? C21 O5 1.3646(19) . ? C21 C22 1.392(2) . ? O5 H5A 0.8400 . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 O6 1.3805(17) . ? C23 C24 1.391(2) . ? O6 H6 0.8400 . ? C24 H24 0.9500 . ? C25 C26 1.488(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 O7 1.216(2) . ? C26 C27 1.483(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.484(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O8 1.213(2) . ? C29 C30 1.485(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? O9 H9A 0.867(14) . ? O9 H9B 0.863(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.40(14) . . ? C6 C1 H1 120.8 . . ? C2 C1 H1 120.8 . . ? O1 C2 C3 117.67(13) . . ? O1 C2 C1 120.98(14) . . ? C3 C2 C1 121.35(14) . . ? C2 O1 H1A 109.5 . . ? C2 C3 C4 119.60(14) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.44(14) . . ? C5 C4 C7 118.98(13) . . ? C3 C4 C7 121.55(13) . . ? C6 C5 C4 119.98(14) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? O2 C6 C5 121.39(14) . . ? O2 C6 C1 117.42(14) . . ? C5 C6 C1 121.19(14) . . ? C6 O2 H2 109.5 . . ? C12 C7 C8 118.63(13) . . ? C12 C7 C4 119.32(13) . . ? C8 C7 C4 121.90(13) . . ? C9 C8 C7 120.99(13) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.11(13) . . ? C8 C9 C13 119.53(12) . . ? C10 C9 C13 121.31(13) . . ? C11 C10 C9 121.16(13) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 118.23(13) . . ? C12 C11 C19 119.07(13) . . ? C10 C11 C19 122.64(13) . . ? C7 C12 C11 121.85(13) . . ? C7 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C18 C13 C14 119.52(13) . . ? C18 C13 C9 119.79(13) . . ? C14 C13 C9 120.69(13) . . ? C15 C14 C13 119.43(14) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? O3 C15 C16 120.56(13) . . ? O3 C15 C14 117.92(14) . . ? C16 C15 C14 121.51(14) . . ? C15 O3 H3A 109.5 . . ? C15 C16 C17 118.71(14) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? O4 C17 C16 117.05(14) . . ? O4 C17 C18 122.03(14) . . ? C16 C17 C18 120.92(15) . . ? C17 O4 H4 109.5 . . ? C17 C18 C13 119.90(14) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C20 C19 C24 119.49(13) . . ? C20 C19 C11 118.57(13) . . ? C24 C19 C11 121.94(13) . . ? C21 C20 C19 120.29(13) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? O5 C21 C20 121.93(13) . . ? O5 C21 C22 117.40(13) . . ? C20 C21 C22 120.67(14) . . ? C21 O5 H5A 109.5 . . ? C23 C22 C21 118.58(13) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? O6 C23 C22 120.77(13) . . ? O6 C23 C24 117.70(13) . . ? C22 C23 C24 121.53(13) . . ? C23 O6 H6 109.5 . . ? C23 C24 C19 119.41(13) . . ? C23 C24 H24 120.3 . . ? C19 C24 H24 120.3 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O7 C26 C27 122.16(18) . . ? O7 C26 C25 120.55(19) . . ? C27 C26 C25 117.29(19) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C29 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O8 C29 C28 121.54(19) . . ? O8 C29 C30 121.02(19) . . ? C28 C29 C30 117.42(18) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? H9A O9 H9B 114.8(17) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 29.08 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.319 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 934378' ####################################################################### # # 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_e2124a #TrackingRef '3,3,5,5-tetramethoxy-1,14,1-terphenyl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 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 _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 13.0066(5) _cell_length_b 8.3251(3) _cell_length_c 8.5054(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.143(2) _cell_angle_gamma 90.00 _cell_volume 884.66(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7693 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 29.77 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9911 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21371 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2550 _reflns_number_gt 2003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.2769P] 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 2550 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.66028(9) 0.01907(15) 0.32137(15) 0.0225(3) Uani 1 1 d . . . C2 C 0.63869(10) -0.04176(16) 0.16242(15) 0.0246(3) Uani 1 1 d . . . H2 H 0.5715 -0.0903 0.1123 0.030 Uiso 1 1 calc R . . C3 C 0.71607(10) -0.03104(16) 0.07737(16) 0.0251(3) Uani 1 1 d . . . C4 C 0.81565(10) 0.03864(16) 0.14806(16) 0.0265(3) Uani 1 1 d . . . H4 H 0.8679 0.0458 0.0895 0.032 Uiso 1 1 calc R . . C5 C 0.83631(10) 0.09775(17) 0.30770(17) 0.0274(3) Uani 1 1 d . . . C6 C 0.75990(10) 0.08964(16) 0.39406(16) 0.0268(3) Uani 1 1 d . . . H6 H 0.7753 0.1318 0.5019 0.032 Uiso 1 1 calc R . . O1 O 0.68584(9) -0.09138(14) -0.07877(13) 0.0379(3) Uani 1 1 d . . . C7 C 0.75888(12) -0.0780(2) -0.17526(17) 0.0347(3) Uani 1 1 d . . . H7A H 0.7778 0.0351 -0.1828 0.052 Uiso 1 1 calc R . . H7B H 0.7255 -0.1200 -0.2853 0.052 Uiso 1 1 calc R . . H7C H 0.8236 -0.1400 -0.1242 0.052 Uiso 1 1 calc R . . O2 O 0.93206(8) 0.16819(15) 0.38980(13) 0.0411(3) Uani 1 1 d . . . C8 C 1.01837(11) 0.1553(2) 0.3168(2) 0.0403(4) Uani 1 1 d . . . H8A H 1.0296 0.0422 0.2945 0.060 Uiso 1 1 calc R . . H8B H 1.0837 0.1990 0.3919 0.060 Uiso 1 1 calc R . . H8C H 1.0009 0.2161 0.2141 0.060 Uiso 1 1 calc R . . C9 C 0.57776(9) 0.00946(15) 0.41221(15) 0.0220(3) Uani 1 1 d . . . C10 C 0.50642(10) -0.11994(15) 0.38970(15) 0.0241(3) Uani 1 1 d . . . H10 H 0.5101 -0.2026 0.3145 0.029 Uiso 1 1 calc R . . C11 C 0.56980(10) 0.12897(15) 0.52385(16) 0.0248(3) Uani 1 1 d . . . H11 H 0.6174 0.2180 0.5409 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0229(5) 0.0219(6) 0.0254(6) 0.0021(4) 0.0110(4) 0.0016(4) C2 0.0234(6) 0.0260(6) 0.0265(6) 0.0003(5) 0.0103(5) -0.0023(5) C3 0.0285(6) 0.0251(6) 0.0243(6) -0.0005(5) 0.0119(5) 0.0000(5) C4 0.0252(6) 0.0284(6) 0.0301(6) 0.0006(5) 0.0143(5) 0.0002(5) C5 0.0229(6) 0.0305(7) 0.0309(7) -0.0023(5) 0.0107(5) -0.0037(5) C6 0.0260(6) 0.0311(7) 0.0258(6) -0.0037(5) 0.0112(5) -0.0022(5) O1 0.0381(6) 0.0531(7) 0.0279(5) -0.0113(5) 0.0180(4) -0.0135(5) C7 0.0376(7) 0.0450(9) 0.0264(7) -0.0008(6) 0.0170(6) 0.0002(6) O2 0.0267(5) 0.0610(8) 0.0394(6) -0.0162(5) 0.0155(4) -0.0152(5) C8 0.0255(6) 0.0548(10) 0.0447(8) -0.0060(7) 0.0165(6) -0.0095(6) C9 0.0210(5) 0.0236(6) 0.0231(6) 0.0014(4) 0.0091(4) 0.0016(4) C10 0.0254(6) 0.0236(6) 0.0257(6) -0.0026(5) 0.0109(5) 0.0001(4) C11 0.0250(6) 0.0228(6) 0.0292(6) -0.0019(5) 0.0117(5) -0.0028(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 C2 1.3971(18) . ? C1 C6 1.4003(17) . ? C1 C9 1.4888(15) . ? C2 C3 1.3961(16) . ? C2 H2 0.9500 . ? C3 O1 1.3713(16) . ? C3 C4 1.3937(18) . ? C4 C5 1.3983(18) . ? C4 H4 0.9500 . ? C5 O2 1.3780(16) . ? C5 C6 1.3920(17) . ? C6 H6 0.9500 . ? O1 C7 1.4219(15) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O2 C8 1.4299(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.3989(17) . ? C9 C10 1.3998(18) . ? C10 C11 1.3910(16) 3_656 ? C10 H10 0.9500 . ? C11 C10 1.3910(16) 3_656 ? C11 H11 0.9500 . ? 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 C6 119.45(11) . . ? C2 C1 C9 120.18(11) . . ? C6 C1 C9 120.37(11) . . ? C3 C2 C1 119.89(11) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? O1 C3 C4 123.51(11) . . ? O1 C3 C2 115.12(11) . . ? C4 C3 C2 121.36(12) . . ? C3 C4 C5 118.04(11) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? O2 C5 C6 115.50(12) . . ? O2 C5 C4 122.99(11) . . ? C6 C5 C4 121.51(12) . . ? C5 C6 C1 119.74(12) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C3 O1 C7 118.21(11) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 O2 C8 117.14(11) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 117.96(11) . . ? C11 C9 C1 120.94(11) . . ? C10 C9 C1 121.10(11) . . ? C11 C10 C9 120.80(11) 3_656 . ? C11 C10 H10 119.6 3_656 . ? C9 C10 H10 119.6 . . ? C10 C11 C9 121.23(11) 3_656 . ? C10 C11 H11 119.4 3_656 . ? C9 C11 H11 119.4 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.311 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 934380' ####################################################################### # # 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_e2122a #TrackingRef '5-(3,5-dimethoxyphenyl)-3,3,5,5-tetramethoxy-1,13,1-terphenyl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 O6' _chemical_formula_sum 'C30 H30 O6' _chemical_formula_weight 486.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.6996(4) _cell_length_b 10.8140(4) _cell_length_c 11.0347(4) _cell_angle_alpha 84.070(2) _cell_angle_beta 89.396(2) _cell_angle_gamma 87.954(2) _cell_volume 1269.10(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5423 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9921 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22207 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5896 _reflns_number_gt 4116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.4451P] 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 5896 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1573 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.93894(16) 0.80327(17) 0.98200(15) 0.0197(4) Uani 1 1 d . . . C2 C 0.83275(16) 0.87767(17) 1.00291(15) 0.0199(4) Uani 1 1 d . . . H2 H 0.7786 0.8531 1.0691 0.024 Uiso 1 1 calc R . . C3 C 0.80493(16) 0.98727(17) 0.92825(15) 0.0196(4) Uani 1 1 d . . . C4 C 0.88477(16) 1.02130(17) 0.82995(15) 0.0204(4) Uani 1 1 d . . . H4 H 0.8674 1.0961 0.7790 0.024 Uiso 1 1 calc R . . C5 C 0.98974(16) 0.94661(17) 0.80572(15) 0.0201(4) Uani 1 1 d . . . C6 C 1.01647(16) 0.83852(17) 0.88245(15) 0.0200(4) Uani 1 1 d . . . H6 H 1.0883 0.7881 0.8670 0.024 Uiso 1 1 calc R . . C7 C 0.96952(17) 0.68757(17) 1.06317(15) 0.0200(4) Uani 1 1 d . . . C8 C 1.09347(17) 0.65684(17) 1.09561(16) 0.0225(4) Uani 1 1 d . . . H8 H 1.1581 0.7114 1.0688 0.027 Uiso 1 1 calc R . . C9 C 1.12191(17) 0.54604(19) 1.16727(16) 0.0247(4) Uani 1 1 d . . . C10 C 1.02862(18) 0.46592(18) 1.20920(16) 0.0259(4) Uani 1 1 d . . . H10 H 1.0483 0.3911 1.2593 0.031 Uiso 1 1 calc R . . C11 C 0.90503(18) 0.49808(18) 1.17591(16) 0.0242(4) Uani 1 1 d . . . C12 C 0.87434(17) 0.60693(17) 1.10363(16) 0.0224(4) Uani 1 1 d . . . H12 H 0.7899 0.6269 1.0816 0.027 Uiso 1 1 calc R . . O1 O 1.24724(13) 0.52244(14) 1.19034(14) 0.0364(4) Uani 1 1 d . . . C13 C 1.2848(2) 0.3994(2) 1.2393(2) 0.0434(6) Uani 1 1 d . . . H13A H 1.2544 0.3843 1.3234 0.065 Uiso 1 1 calc R . . H13B H 1.3762 0.3906 1.2379 0.065 Uiso 1 1 calc R . . H13C H 1.2494 0.3390 1.1900 0.065 Uiso 1 1 calc R . . O2 O 0.81848(13) 0.41242(14) 1.22046(14) 0.0343(4) Uani 1 1 d . . . C14 C 0.6948(2) 0.4275(2) 1.1719(2) 0.0390(5) Uani 1 1 d . . . H14A H 0.6570 0.5067 1.1923 0.058 Uiso 1 1 calc R . . H14B H 0.6440 0.3589 1.2071 0.058 Uiso 1 1 calc R . . H14C H 0.6986 0.4273 1.0832 0.058 Uiso 1 1 calc R . . C15 C 0.69287(16) 1.06790(17) 0.95236(16) 0.0211(4) Uani 1 1 d . . . C16 C 0.64857(16) 1.07346(18) 1.07170(16) 0.0226(4) Uani 1 1 d . . . H16 H 0.6899 1.0265 1.1380 0.027 Uiso 1 1 calc R . . C17 C 0.54334(16) 1.14840(18) 1.09254(17) 0.0245(4) Uani 1 1 d . . . C18 C 0.48348(17) 1.21941(19) 0.99655(18) 0.0273(4) Uani 1 1 d . . . H18 H 0.4128 1.2716 1.0115 0.033 Uiso 1 1 calc R . . C19 C 0.52795(17) 1.21332(19) 0.87885(18) 0.0270(4) Uani 1 1 d . . . C20 C 0.63234(16) 1.13789(18) 0.85509(17) 0.0239(4) Uani 1 1 d . . . H20 H 0.6618 1.1342 0.7740 0.029 Uiso 1 1 calc R . . O3 O 0.49192(13) 1.16066(14) 1.20553(12) 0.0329(4) Uani 1 1 d . . . C21 C 0.5486(2) 1.0885(2) 1.30754(18) 0.0388(5) Uani 1 1 d . . . H21A H 0.5483 1.0001 1.2950 0.058 Uiso 1 1 calc R . . H21B H 0.5014 1.1024 1.3818 0.058 Uiso 1 1 calc R . . H21C H 0.6350 1.1135 1.3157 0.058 Uiso 1 1 calc R . . O4 O 0.45979(13) 1.28310(16) 0.78904(13) 0.0401(4) Uani 1 1 d . . . C22 C 0.5173(2) 1.3041(3) 0.6720(2) 0.0498(7) Uani 1 1 d . . . H22A H 0.6001 1.3381 0.6805 0.075 Uiso 1 1 calc R . . H22B H 0.4654 1.3634 0.6195 0.075 Uiso 1 1 calc R . . H22C H 0.5261 1.2253 0.6356 0.075 Uiso 1 1 calc R . . C23 C 1.06973(16) 0.97978(17) 0.69599(15) 0.0201(4) Uani 1 1 d . . . C24 C 1.10377(17) 1.10251(18) 0.66398(16) 0.0233(4) Uani 1 1 d . . . H24 H 1.0799 1.1660 0.7138 0.028 Uiso 1 1 calc R . . C25 C 1.17337(18) 1.13030(18) 0.55767(16) 0.0251(4) Uani 1 1 d . . . C26 C 1.20863(17) 1.03815(19) 0.48328(16) 0.0252(4) Uani 1 1 d . . . H26 H 1.2549 1.0583 0.4104 0.030 Uiso 1 1 calc R . . C27 C 1.17523(16) 0.91690(18) 0.51715(16) 0.0227(4) Uani 1 1 d . . . C28 C 1.10687(16) 0.88629(18) 0.62359(16) 0.0219(4) Uani 1 1 d . . . H28 H 1.0857 0.8025 0.6467 0.026 Uiso 1 1 calc R . . O5 O 1.21065(16) 1.24775(14) 0.51664(13) 0.0386(4) Uani 1 1 d . . . C29 C 1.1896(2) 1.3429(2) 0.5954(2) 0.0379(5) Uani 1 1 d . . . H29A H 1.0995 1.3551 0.6090 0.057 Uiso 1 1 calc R . . H29B H 1.2239 1.4206 0.5579 0.057 Uiso 1 1 calc R . . H29C H 1.2308 1.3184 0.6735 0.057 Uiso 1 1 calc R . . O6 O 1.21401(13) 0.83060(13) 0.43955(12) 0.0300(3) Uani 1 1 d . . . C30 C 1.1733(2) 0.7073(2) 0.4670(2) 0.0368(5) Uani 1 1 d . . . H30A H 1.2125 0.6701 0.5426 0.055 Uiso 1 1 calc R . . H30B H 1.1971 0.6579 0.4003 0.055 Uiso 1 1 calc R . . H30C H 1.0822 0.7089 0.4770 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(8) 0.0144(10) 0.0213(8) -0.0034(7) 0.0002(7) 0.0011(7) C2 0.0235(8) 0.0160(10) 0.0200(8) -0.0014(7) 0.0022(6) -0.0002(7) C3 0.0207(8) 0.0166(10) 0.0216(8) -0.0036(7) 0.0001(6) 0.0012(7) C4 0.0254(9) 0.0143(10) 0.0211(8) -0.0008(7) -0.0002(7) 0.0015(7) C5 0.0221(8) 0.0177(10) 0.0210(8) -0.0044(7) 0.0012(6) -0.0009(7) C6 0.0215(8) 0.0153(10) 0.0230(8) -0.0024(7) 0.0003(7) 0.0033(7) C7 0.0280(9) 0.0142(10) 0.0180(8) -0.0035(7) 0.0027(7) 0.0027(7) C8 0.0270(9) 0.0155(11) 0.0244(9) 0.0000(7) 0.0014(7) 0.0018(7) C9 0.0279(9) 0.0213(11) 0.0247(9) -0.0029(8) 0.0000(7) 0.0049(7) C10 0.0374(10) 0.0157(11) 0.0235(9) 0.0012(7) 0.0039(8) 0.0044(8) C11 0.0322(10) 0.0144(11) 0.0258(9) -0.0019(7) 0.0077(7) -0.0001(7) C12 0.0264(9) 0.0162(11) 0.0244(9) -0.0031(7) 0.0020(7) 0.0025(7) O1 0.0287(7) 0.0284(10) 0.0491(9) 0.0082(7) -0.0052(6) 0.0084(6) C13 0.0424(13) 0.0369(16) 0.0469(13) 0.0082(11) -0.0032(10) 0.0179(10) O2 0.0337(8) 0.0201(9) 0.0469(9) 0.0065(6) 0.0088(6) -0.0029(6) C14 0.0331(11) 0.0253(13) 0.0582(14) -0.0019(10) 0.0076(10) -0.0055(9) C15 0.0196(8) 0.0143(10) 0.0294(9) -0.0027(7) 0.0016(7) -0.0006(7) C16 0.0223(8) 0.0201(11) 0.0251(9) -0.0019(7) 0.0000(7) 0.0021(7) C17 0.0212(9) 0.0249(12) 0.0282(9) -0.0073(8) 0.0028(7) -0.0015(7) C18 0.0216(9) 0.0243(12) 0.0363(10) -0.0065(8) 0.0014(7) 0.0063(7) C19 0.0240(9) 0.0243(12) 0.0320(10) -0.0003(8) -0.0026(7) 0.0035(8) C20 0.0231(9) 0.0217(11) 0.0264(9) -0.0012(8) 0.0016(7) 0.0010(7) O3 0.0293(7) 0.0406(10) 0.0288(7) -0.0078(6) 0.0031(6) 0.0096(6) C21 0.0325(11) 0.0550(16) 0.0282(10) -0.0042(10) 0.0035(8) 0.0057(10) O4 0.0319(8) 0.0483(11) 0.0366(8) 0.0066(7) 0.0000(6) 0.0179(7) C22 0.0427(13) 0.061(2) 0.0402(13) 0.0156(12) 0.0017(10) 0.0186(12) C23 0.0199(8) 0.0200(11) 0.0201(8) -0.0007(7) 0.0006(6) 0.0011(7) C24 0.0297(9) 0.0182(11) 0.0220(9) -0.0031(7) 0.0017(7) 0.0019(7) C25 0.0340(10) 0.0186(11) 0.0219(9) 0.0021(7) 0.0005(7) -0.0033(8) C26 0.0289(9) 0.0263(12) 0.0200(8) -0.0001(8) 0.0042(7) -0.0011(8) C27 0.0244(9) 0.0238(11) 0.0200(8) -0.0038(7) 0.0004(7) 0.0039(7) C28 0.0231(9) 0.0174(11) 0.0245(9) -0.0005(7) 0.0005(7) 0.0023(7) O5 0.0655(11) 0.0212(9) 0.0294(7) -0.0024(6) 0.0150(7) -0.0118(7) C29 0.0533(14) 0.0221(13) 0.0394(12) -0.0067(9) 0.0084(10) -0.0083(10) O6 0.0411(8) 0.0222(8) 0.0266(7) -0.0045(6) 0.0088(6) 0.0041(6) C30 0.0513(13) 0.0219(13) 0.0385(11) -0.0109(9) 0.0094(10) 0.0005(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 1.399(2) . ? C1 C2 1.400(2) . ? C1 C7 1.490(3) . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.401(2) . ? C3 C15 1.495(2) . ? C4 C5 1.400(2) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 C23 1.496(2) . ? C6 H6 0.9500 . ? C7 C8 1.397(2) . ? C7 C12 1.404(3) . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 O1 1.377(2) . ? C9 C10 1.389(3) . ? C10 C11 1.398(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 O2 1.384(2) . ? C12 H12 0.9500 . ? O1 C13 1.429(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 C14 1.431(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.399(3) . ? C15 C16 1.401(2) . ? C16 C17 1.395(2) . ? C16 H16 0.9500 . ? C17 O3 1.375(2) . ? C17 C18 1.390(3) . ? C18 C19 1.386(3) . ? C18 H18 0.9500 . ? C19 O4 1.380(2) . ? C19 C20 1.398(3) . ? C20 H20 0.9500 . ? O3 C21 1.429(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O4 C22 1.425(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C28 1.396(2) . ? C23 C24 1.398(3) . ? C24 C25 1.395(2) . ? C24 H24 0.9500 . ? C25 O5 1.375(2) . ? C25 C26 1.395(3) . ? C26 C27 1.384(3) . ? C26 H26 0.9500 . ? C27 O6 1.381(2) . ? C27 C28 1.394(2) . ? C28 H28 0.9500 . ? O5 C29 1.424(2) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? O6 C30 1.419(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.96(17) . . ? C6 C1 C7 119.95(16) . . ? C2 C1 C7 121.09(16) . . ? C3 C2 C1 121.25(16) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 118.70(16) . . ? C2 C3 C15 121.12(16) . . ? C4 C3 C15 120.17(17) . . ? C5 C4 C3 120.92(17) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 119.31(16) . . ? C6 C5 C23 120.25(16) . . ? C4 C5 C23 120.40(17) . . ? C5 C6 C1 120.83(16) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 119.83(17) . . ? C8 C7 C1 120.10(16) . . ? C12 C7 C1 120.03(16) . . ? C9 C8 C7 119.77(17) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? O1 C9 C10 123.75(18) . . ? O1 C9 C8 115.15(17) . . ? C10 C9 C8 121.09(18) . . ? C9 C10 C11 118.40(18) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 O2 123.78(17) . . ? C12 C11 C10 121.69(17) . . ? O2 C11 C10 114.53(17) . . ? C11 C12 C7 119.21(17) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? C9 O1 C13 117.47(17) . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 O2 C14 117.29(16) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 120.09(16) . . ? C20 C15 C3 119.65(16) . . ? C16 C15 C3 120.27(16) . . ? C17 C16 C15 119.55(17) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? O3 C17 C18 114.83(16) . . ? O3 C17 C16 124.42(17) . . ? C18 C17 C16 120.74(17) . . ? C19 C18 C17 119.29(17) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? O4 C19 C18 115.24(17) . . ? O4 C19 C20 123.52(17) . . ? C18 C19 C20 121.21(18) . . ? C19 C20 C15 119.11(17) . . ? C19 C20 H20 120.4 . . ? C15 C20 H20 120.4 . . ? C17 O3 C21 117.30(15) . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 O4 C22 116.98(16) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 120.35(16) . . ? C28 C23 C5 118.72(17) . . ? C24 C23 C5 120.90(16) . . ? C25 C24 C23 118.98(17) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? O5 C25 C26 114.89(16) . . ? O5 C25 C24 123.96(17) . . ? C26 C25 C24 121.14(18) . . ? C27 C26 C25 119.05(17) . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? O6 C27 C26 115.83(16) . . ? O6 C27 C28 123.17(18) . . ? C26 C27 C28 121.00(17) . . ? C27 C28 C23 119.45(18) . . ? C27 C28 H28 120.3 . . ? C23 C28 H28 120.3 . . ? C25 O5 C29 117.31(15) . . ? O5 C29 H29A 109.5 . . ? O5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 O6 C30 117.11(15) . . ? O6 C30 H30A 109.5 . . ? O6 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O6 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.329 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 934381' ####################################################################### # # 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_e2164a #TrackingRef 's2164 (1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C57 H52 O8' _chemical_formula_sum 'C57 H52 O8' _chemical_formula_weight 864.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 27.539(2) _cell_length_b 7.4754(4) _cell_length_c 25.6914(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5289.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1973 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 22.11 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9957 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_process_details sadabs _exptl_special_details ; Owing to large disorder of the solvent present in the cavities of this structure, the SQUEEZE command has been applied. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38147 _diffrn_reflns_av_R_equivalents 0.1237 _diffrn_reflns_av_sigmaI/netI 0.0982 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.36 _reflns_number_total 6409 _reflns_number_gt 3193 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0995P)^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 SHELXL _refine_ls_extinction_coef 0.00016(1) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6409 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1466 _refine_ls_R_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.2031 _refine_ls_wR_factor_gt 0.1819 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.0000 0.8787(4) 0.2500 0.0234(8) Uani 1 2 d S . . C2 C 0.04137(9) 0.7506(3) 0.23282(10) 0.0240(6) Uani 1 1 d . . . C3 C 0.05635(10) 0.6188(3) 0.26743(10) 0.0325(6) Uani 1 1 d . . . H3 H 0.0432 0.6183 0.3016 0.039 Uiso 1 1 calc R . . C4 C 0.08946(10) 0.4892(3) 0.25405(11) 0.0335(7) Uani 1 1 d . . . H4 H 0.0990 0.4034 0.2793 0.040 Uiso 1 1 calc R . . C5 C 0.10931(9) 0.4810(3) 0.20437(10) 0.0261(6) Uani 1 1 d . . . C6 C 0.09515(9) 0.6148(4) 0.16972(10) 0.0305(6) Uani 1 1 d . . . H6 H 0.1084 0.6159 0.1356 0.037 Uiso 1 1 calc R . . C7 C 0.06204(10) 0.7468(3) 0.18389(10) 0.0288(6) Uani 1 1 d . . . H7 H 0.0535 0.8363 0.1593 0.035 Uiso 1 1 calc R . . C8 C 0.14222(9) 0.3317(3) 0.18879(10) 0.0278(6) Uani 1 1 d . . . C9 C 0.14854(9) 0.1869(3) 0.22183(11) 0.0326(6) Uani 1 1 d . . . H9 H 0.1324 0.1853 0.2545 0.039 Uiso 1 1 calc R . . C10 C 0.17812(9) 0.0440(4) 0.20779(12) 0.0335(7) Uani 1 1 d . . . C11 C 0.20229(10) 0.0441(4) 0.16073(12) 0.0362(7) Uani 1 1 d . . . H11 H 0.2228 -0.0528 0.1512 0.043 Uiso 1 1 calc R . . C12 C 0.19600(10) 0.1896(4) 0.12740(11) 0.0351(7) Uani 1 1 d . . . C13 C 0.16658(9) 0.3331(4) 0.14056(11) 0.0321(6) Uani 1 1 d . . . H13 H 0.1629 0.4312 0.1174 0.038 Uiso 1 1 calc R . . O1 O 0.18141(7) -0.0886(3) 0.24427(9) 0.0489(6) Uani 1 1 d . . . C14 C 0.21294(12) -0.2348(4) 0.23321(16) 0.0550(9) Uani 1 1 d . . . H14A H 0.2035 -0.2898 0.2001 0.083 Uiso 1 1 calc R . . H14B H 0.2106 -0.3237 0.2611 0.083 Uiso 1 1 calc R . . H14C H 0.2465 -0.1915 0.2308 0.083 Uiso 1 1 calc R . . O2 O 0.22167(8) 0.1789(3) 0.08215(8) 0.0473(6) Uani 1 1 d . . . C15 C 0.21226(12) 0.3068(4) 0.04262(12) 0.0487(8) Uani 1 1 d . . . H15A H 0.1775 0.3074 0.0346 0.073 Uiso 1 1 calc R . . H15B H 0.2307 0.2756 0.0113 0.073 Uiso 1 1 calc R . . H15C H 0.2221 0.4257 0.0547 0.073 Uiso 1 1 calc R . . C16 C 0.01689(9) 1.0023(3) 0.29446(10) 0.0247(6) Uani 1 1 d . . . C17 C 0.06358(9) 1.0002(3) 0.31502(10) 0.0266(6) Uani 1 1 d . . . H17 H 0.0868 0.9183 0.3017 0.032 Uiso 1 1 calc R . . C18 C 0.07662(9) 1.1168(3) 0.35489(10) 0.0278(6) Uani 1 1 d . . . H18 H 0.1088 1.1131 0.3681 0.033 Uiso 1 1 calc R . . C19 C 0.04406(9) 1.2380(3) 0.37577(10) 0.0260(6) Uani 1 1 d . . . C20 C -0.00221(10) 1.2440(3) 0.35395(10) 0.0278(6) Uani 1 1 d . . . H20 H -0.0252 1.3280 0.3668 0.033 Uiso 1 1 calc R . . C21 C -0.01534(9) 1.1302(3) 0.31408(10) 0.0269(6) Uani 1 1 d . . . H21 H -0.0470 1.1390 0.2996 0.032 Uiso 1 1 calc R . . C22 C 0.05747(9) 1.3522(3) 0.42098(9) 0.0262(6) Uani 1 1 d . . . C23 C 0.08813(10) 1.2848(4) 0.45921(10) 0.0312(6) Uani 1 1 d . . . H23 H 0.1011 1.1676 0.4562 0.037 Uiso 1 1 calc R . . C24 C 0.09961(10) 1.3906(4) 0.50189(10) 0.0323(6) Uani 1 1 d . . . C25 C 0.08062(10) 1.5596(4) 0.50738(11) 0.0337(7) Uani 1 1 d . . . H25 H 0.0883 1.6297 0.5371 0.040 Uiso 1 1 calc R . . C26 C 0.05024(10) 1.6268(4) 0.46919(10) 0.0302(6) Uani 1 1 d . . . C27 C 0.03830(10) 1.5236(3) 0.42590(10) 0.0292(6) Uani 1 1 d . . . H27 H 0.0172 1.5699 0.3999 0.035 Uiso 1 1 calc R . . O3 O 0.12929(8) 1.3339(3) 0.54181(8) 0.0463(6) Uani 1 1 d . . . C28 C 0.14950(15) 1.1595(5) 0.53853(14) 0.0630(11) Uani 1 1 d . . . H28A H 0.1233 1.0710 0.5370 0.094 Uiso 1 1 calc R . . H28B H 0.1697 1.1369 0.5692 0.094 Uiso 1 1 calc R . . H28C H 0.1695 1.1503 0.5071 0.094 Uiso 1 1 calc R . . O4 O 0.03326(8) 1.7956(2) 0.47764(8) 0.0419(5) Uani 1 1 d . . . C29 C -0.00077(11) 1.8649(4) 0.44125(11) 0.0386(7) Uani 1 1 d . . . H29A H 0.0148 1.8764 0.4071 0.058 Uiso 1 1 calc R . . H29B H -0.0120 1.9827 0.4530 0.058 Uiso 1 1 calc R . . H29C H -0.0285 1.7835 0.4386 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0294(18) 0.019(2) 0.0221(18) 0.000 -0.0016(15) 0.000 C2 0.0315(14) 0.0152(13) 0.0254(13) -0.0006(11) -0.0008(11) -0.0007(10) C3 0.0473(16) 0.0266(16) 0.0235(13) 0.0003(12) 0.0056(12) 0.0070(13) C4 0.0468(17) 0.0249(16) 0.0289(14) 0.0041(12) 0.0011(12) 0.0099(13) C5 0.0272(13) 0.0222(15) 0.0289(14) -0.0056(11) -0.0009(11) -0.0004(11) C6 0.0320(14) 0.0328(16) 0.0268(14) 0.0021(12) 0.0037(11) 0.0041(12) C7 0.0369(14) 0.0243(15) 0.0252(13) 0.0052(11) 0.0002(12) 0.0015(12) C8 0.0220(12) 0.0233(15) 0.0381(15) -0.0038(12) -0.0031(11) -0.0005(10) C9 0.0284(14) 0.0284(16) 0.0411(16) 0.0007(13) 0.0057(12) 0.0007(12) C10 0.0251(13) 0.0252(16) 0.0501(18) -0.0011(13) 0.0001(13) 0.0009(11) C11 0.0262(14) 0.0272(17) 0.0552(19) -0.0110(14) -0.0021(13) 0.0038(11) C12 0.0293(14) 0.0363(18) 0.0397(16) -0.0106(14) 0.0047(13) -0.0031(12) C13 0.0324(15) 0.0292(16) 0.0346(15) -0.0044(12) 0.0001(12) 0.0012(12) O1 0.0470(12) 0.0330(12) 0.0666(15) 0.0110(11) 0.0140(11) 0.0173(10) C14 0.0428(18) 0.0352(19) 0.087(3) 0.0100(18) 0.0073(18) 0.0166(14) O2 0.0523(13) 0.0444(13) 0.0451(13) -0.0069(10) 0.0132(11) 0.0105(10) C15 0.0471(19) 0.056(2) 0.0430(19) -0.0040(16) 0.0094(15) 0.0022(16) C16 0.0335(14) 0.0167(13) 0.0239(13) 0.0023(10) -0.0008(11) -0.0011(11) C17 0.0292(13) 0.0219(14) 0.0288(13) 0.0021(11) 0.0021(11) 0.0029(11) C18 0.0266(13) 0.0304(15) 0.0264(13) 0.0008(12) -0.0027(11) -0.0003(12) C19 0.0324(14) 0.0205(14) 0.0250(13) 0.0007(11) -0.0026(11) -0.0020(11) C20 0.0355(14) 0.0212(14) 0.0267(13) -0.0013(11) -0.0016(11) 0.0062(11) C21 0.0287(13) 0.0238(15) 0.0281(14) -0.0019(11) -0.0053(11) 0.0033(11) C22 0.0310(13) 0.0244(15) 0.0233(13) -0.0017(11) 0.0003(11) -0.0024(11) C23 0.0355(15) 0.0291(16) 0.0288(14) -0.0015(12) -0.0016(12) 0.0039(12) C24 0.0341(14) 0.0360(17) 0.0269(14) 0.0001(12) -0.0044(12) 0.0014(13) C25 0.0393(15) 0.0322(17) 0.0296(15) -0.0087(12) -0.0031(12) -0.0024(13) C26 0.0375(15) 0.0235(16) 0.0297(14) -0.0042(12) 0.0031(12) -0.0020(12) C27 0.0362(15) 0.0255(15) 0.0258(14) -0.0003(11) -0.0032(11) 0.0001(11) O3 0.0563(14) 0.0494(14) 0.0331(11) -0.0059(10) -0.0160(10) 0.0146(11) C28 0.073(3) 0.063(2) 0.053(2) -0.0087(18) -0.0272(19) 0.035(2) O4 0.0621(14) 0.0258(12) 0.0379(12) -0.0095(9) -0.0108(10) 0.0096(10) C29 0.0527(18) 0.0280(16) 0.0349(16) -0.0046(13) 0.0016(14) 0.0074(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 C16 1.541(3) 3 ? C1 C16 1.541(3) . ? C1 C2 1.552(3) 3 ? C1 C2 1.552(3) . ? C2 C7 1.380(4) . ? C2 C3 1.389(3) . ? C3 C4 1.374(4) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(4) . ? C5 C8 1.493(3) . ? C6 C7 1.392(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.386(4) . ? C8 C13 1.409(4) . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C10 O1 1.368(3) . ? C10 C11 1.380(4) . ? C11 C12 1.395(4) . ? C11 H11 0.9500 . ? C12 O2 1.363(3) . ? C12 C13 1.386(4) . ? C13 H13 0.9500 . ? O1 C14 1.424(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O2 C15 1.418(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.390(4) . ? C16 C21 1.399(3) . ? C17 C18 1.392(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.393(4) . ? C19 C22 1.488(3) . ? C20 C21 1.380(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.390(4) . ? C22 C27 1.392(4) . ? C23 C24 1.388(4) . ? C23 H23 0.9500 . ? C24 C25 1.375(4) . ? C24 O3 1.378(3) . ? C25 C26 1.384(4) . ? C25 H25 0.9500 . ? C26 O4 1.363(3) . ? C26 C27 1.393(4) . ? C27 H27 0.9500 . ? O3 C28 1.420(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O4 C29 1.421(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C1 C16 106.3(3) 3 . ? C16 C1 C2 111.05(13) 3 3 ? C16 C1 C2 112.38(13) . 3 ? C16 C1 C2 112.38(13) 3 . ? C16 C1 C2 111.04(13) . . ? C2 C1 C2 103.8(3) 3 . ? C7 C2 C3 116.5(2) . . ? C7 C2 C1 125.0(2) . . ? C3 C2 C1 118.3(2) . . ? C4 C3 C2 122.5(2) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 121.5(2) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 116.4(2) . . ? C4 C5 C8 121.2(2) . . ? C6 C5 C8 122.4(2) . . ? C7 C6 C5 121.6(2) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C2 C7 C6 121.5(2) . . ? C2 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C9 C8 C13 119.0(2) . . ? C9 C8 C5 119.7(2) . . ? C13 C8 C5 121.3(2) . . ? C8 C9 C10 120.9(3) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? O1 C10 C11 124.7(2) . . ? O1 C10 C9 114.7(3) . . ? C11 C10 C9 120.6(3) . . ? C10 C11 C12 118.6(2) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? O2 C12 C13 123.8(3) . . ? O2 C12 C11 114.4(2) . . ? C13 C12 C11 121.7(3) . . ? C12 C13 C8 119.1(3) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? C10 O1 C14 117.4(2) . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 O2 C15 118.5(2) . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 117.2(2) . . ? C17 C16 C1 123.7(2) . . ? C21 C16 C1 119.0(2) . . ? C16 C17 C18 120.7(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 121.9(2) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 117.3(2) . . ? C18 C19 C22 121.2(2) . . ? C20 C19 C22 121.5(2) . . ? C21 C20 C19 121.2(2) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C16 121.5(2) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? C23 C22 C27 120.0(2) . . ? C23 C22 C19 119.7(2) . . ? C27 C22 C19 120.3(2) . . ? C24 C23 C22 119.4(2) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C25 C24 O3 115.6(2) . . ? C25 C24 C23 121.2(3) . . ? O3 C24 C23 123.2(2) . . ? C24 C25 C26 119.4(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? O4 C26 C25 115.5(2) . . ? O4 C26 C27 124.0(2) . . ? C25 C26 C27 120.5(2) . . ? C22 C27 C26 119.5(2) . . ? C22 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C24 O3 C28 118.1(2) . . ? O3 C28 H28A 109.5 . . ? O3 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O3 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 O4 C29 117.3(2) . . ? O4 C29 H29A 109.5 . . ? O4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.486 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.151 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 -0.026 0.387 275.6 77.9 2 0.250 -0.042 0.887 275.7 77.9 3 0.750 -0.016 0.113 275.6 77.9 4 0.750 -0.056 0.613 275.7 77.9 _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934382' ####################################################################### # # 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_e2135a #TrackingRef '3,3,5,5-tetrahydroxy-1,1-biphenyl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O4, 2(H2 O)' _chemical_formula_sum 'C12 H14 O6' _chemical_formula_weight 254.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9700(2) _cell_length_b 7.4370(3) _cell_length_c 7.9748(4) _cell_angle_alpha 85.355(2) _cell_angle_beta 82.615(2) _cell_angle_gamma 75.241(2) _cell_volume 282.32(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1730 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.55 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 134 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9892 _exptl_absorpt_correction_T_max 0.9940 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2867 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1205 _reflns_number_gt 1055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0807P)^2^+0.1513P] 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 1205 _refine_ls_number_parameters 90 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.060 _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 0.6196(3) 0.9367(2) 0.04030(19) 0.0175(4) Uani 1 1 d . . . C2 C 0.6216(4) 0.9258(2) 0.21638(19) 0.0211(4) Uani 1 1 d . . . H2 H 0.4677 0.9964 0.2859 0.025 Uiso 1 1 calc R . . C3 C 0.8478(4) 0.8121(2) 0.28923(19) 0.0214(4) Uani 1 1 d . . . O1 O 0.8360(3) 0.8096(2) 0.46320(14) 0.0321(4) Uani 1 1 d . . . H1 H 0.9964 0.7624 0.4925 0.048 Uiso 1 1 calc R . . C4 C 1.0747(3) 0.7055(2) 0.19192(19) 0.0207(4) Uani 1 1 d . . . H4 H 1.2286 0.6276 0.2429 0.025 Uiso 1 1 calc R . . C5 C 1.0699(3) 0.7162(2) 0.01769(19) 0.0184(4) Uani 1 1 d . . . O2 O 1.2923(3) 0.61356(17) -0.08152(14) 0.0253(3) Uani 1 1 d . . . H2A H 1.4206 0.5624 -0.0215 0.038 Uiso 1 1 calc R . . C6 C 0.8473(3) 0.8290(2) -0.05828(19) 0.0192(4) Uani 1 1 d . . . H6 H 0.8492 0.8333 -0.1778 0.023 Uiso 1 1 calc R . . O3 O 0.3573(3) 0.6628(2) 0.57518(15) 0.0304(4) Uani 1 1 d D . . H3A H 0.477(5) 0.729(3) 0.546(3) 0.036 Uiso 1 1 d D . . H3B H 0.326(5) 0.627(3) 0.678(2) 0.036 Uiso 1 1 d 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 0.0151(8) 0.0199(7) 0.0158(7) 0.0004(5) -0.0035(6) -0.0006(7) C2 0.0161(8) 0.0266(8) 0.0162(8) -0.0021(6) -0.0010(6) 0.0027(7) C3 0.0197(9) 0.0280(8) 0.0131(7) 0.0003(6) -0.0030(6) 0.0005(7) O1 0.0225(7) 0.0505(8) 0.0133(6) -0.0024(5) -0.0039(4) 0.0105(6) C4 0.0160(8) 0.0245(8) 0.0176(8) 0.0018(6) -0.0050(6) 0.0031(7) C5 0.0149(8) 0.0206(7) 0.0165(7) -0.0017(5) -0.0009(6) 0.0014(7) O2 0.0191(7) 0.0300(7) 0.0177(6) -0.0023(5) -0.0016(5) 0.0106(5) C6 0.0186(8) 0.0228(8) 0.0134(7) -0.0001(5) -0.0030(6) 0.0002(7) O3 0.0287(8) 0.0410(8) 0.0164(6) 0.0007(5) -0.0031(5) -0.0001(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 C6 1.397(2) . ? C1 C2 1.401(2) . ? C1 C1 1.497(3) 2_675 ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 O1 1.3798(18) . ? C3 C4 1.386(2) . ? O1 H1 0.8400 . ? C4 C5 1.388(2) . ? C4 H4 0.9500 . ? C5 O2 1.3689(19) . ? C5 C6 1.383(2) . ? O2 H2A 0.8400 . ? C6 H6 0.9500 . ? O3 H3A 0.864(15) . ? O3 H3B 0.847(15) . ? 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 118.54(15) . . ? C6 C1 C1 120.82(17) . 2_675 ? C2 C1 C1 120.63(18) . 2_675 ? C3 C2 C1 120.13(15) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? O1 C3 C2 116.87(15) . . ? O1 C3 C4 121.59(15) . . ? C2 C3 C4 121.54(14) . . ? C3 O1 H1 109.5 . . ? C3 C4 C5 117.93(15) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? O2 C5 C6 119.17(14) . . ? O2 C5 C4 119.14(14) . . ? C6 C5 C4 121.69(15) . . ? C5 O2 H2A 109.5 . . ? C5 C6 C1 120.16(14) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? H3A O3 H3B 120(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.349 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 934386' ####################################################################### # # 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_e2148a #TrackingRef 's2148.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H26 O4' _chemical_formula_sum 'C28 H26 O4' _chemical_formula_weight 426.49 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 15.6242(12) _cell_length_b 8.1550(6) _cell_length_c 8.4742(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.557(2) _cell_angle_gamma 90.00 _cell_volume 1072.68(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1330 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.57 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9922 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6060 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2637 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.3388P] 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 2637 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.22316(11) 0.9808(2) -0.01641(19) 0.0249(4) Uani 1 1 d . . . C2 C 0.30432(12) 0.9151(2) -0.0300(2) 0.0289(4) Uani 1 1 d . . . H2 H 0.3175 0.8747 -0.1295 0.035 Uiso 1 1 calc R . . C3 C 0.36585(12) 0.9086(2) 0.1012(2) 0.0295(4) Uani 1 1 d . . . C4 C 0.34881(12) 0.9681(2) 0.2481(2) 0.0290(4) Uani 1 1 d . . . H4 H 0.3914 0.9639 0.3375 0.035 Uiso 1 1 calc R . . C5 C 0.26794(12) 1.0338(2) 0.2608(2) 0.0273(4) Uani 1 1 d . . . C6 C 0.20533(12) 1.0402(2) 0.1308(2) 0.0275(4) Uani 1 1 d . . . H6 H 0.1502 1.0850 0.1421 0.033 Uiso 1 1 calc R . . O1 O 0.44348(9) 0.8403(2) 0.07518(16) 0.0441(4) Uani 1 1 d . . . C7 C 0.51246(13) 0.8533(3) 0.1998(2) 0.0426(5) Uani 1 1 d . . . H7A H 0.5221 0.9690 0.2278 0.064 Uiso 1 1 calc R . . H7B H 0.5650 0.8072 0.1644 0.064 Uiso 1 1 calc R . . H7C H 0.4978 0.7927 0.2929 0.064 Uiso 1 1 calc R . . O2 O 0.24334(9) 1.09406(19) 0.39915(14) 0.0390(4) Uani 1 1 d . . . C8 C 0.30408(14) 1.0873(3) 0.5374(2) 0.0382(5) Uani 1 1 d . . . H8A H 0.3222 0.9735 0.5578 0.057 Uiso 1 1 calc R . . H8B H 0.2775 1.1295 0.6286 0.057 Uiso 1 1 calc R . . H8C H 0.3544 1.1543 0.5212 0.057 Uiso 1 1 calc R . . C9 C 0.15672(11) 0.9861(2) -0.15680(19) 0.0241(4) Uani 1 1 d . . . C10 C 0.15688(12) 0.8724(2) -0.2785(2) 0.0297(4) Uani 1 1 d . . . H10 H 0.1995 0.7888 -0.2708 0.036 Uiso 1 1 calc R . . C11 C 0.09625(12) 0.8780(2) -0.4112(2) 0.0289(4) Uani 1 1 d . . . H11 H 0.0985 0.7985 -0.4925 0.035 Uiso 1 1 calc R . . C12 C 0.03237(11) 0.9969(2) -0.42830(19) 0.0236(4) Uani 1 1 d . . . C13 C 0.03239(13) 1.1106(3) -0.3057(2) 0.0386(5) Uani 1 1 d . . . H13 H -0.0105 1.1937 -0.3131 0.046 Uiso 1 1 calc R . . C14 C 0.09305(13) 1.1059(3) -0.1733(2) 0.0377(5) Uani 1 1 d . . . H14 H 0.0911 1.1859 -0.0923 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0271(9) 0.0236(9) 0.0223(8) 0.0020(7) -0.0046(7) -0.0012(7) C2 0.0303(9) 0.0322(10) 0.0230(8) -0.0015(7) -0.0023(7) 0.0013(8) C3 0.0240(9) 0.0328(10) 0.0300(9) -0.0002(8) -0.0044(7) 0.0019(8) C4 0.0305(9) 0.0294(10) 0.0245(8) 0.0012(7) -0.0086(7) -0.0008(8) C5 0.0326(10) 0.0262(9) 0.0218(8) 0.0000(7) -0.0023(7) -0.0021(8) C6 0.0269(9) 0.0276(10) 0.0262(8) 0.0003(7) -0.0042(7) 0.0012(8) O1 0.0298(7) 0.0640(11) 0.0355(8) -0.0105(7) -0.0089(6) 0.0144(7) C7 0.0277(10) 0.0557(14) 0.0410(11) -0.0048(10) -0.0102(9) 0.0087(10) O2 0.0395(8) 0.0541(10) 0.0214(6) -0.0082(6) -0.0052(6) 0.0090(7) C8 0.0444(12) 0.0473(13) 0.0205(8) -0.0023(8) -0.0064(8) 0.0000(10) C9 0.0235(8) 0.0271(9) 0.0203(7) 0.0018(7) -0.0031(6) -0.0016(7) C10 0.0269(9) 0.0293(10) 0.0305(9) -0.0027(7) -0.0064(7) 0.0066(8) C11 0.0313(9) 0.0292(10) 0.0244(8) -0.0063(7) -0.0046(7) 0.0040(8) C12 0.0226(8) 0.0268(9) 0.0205(8) 0.0010(6) -0.0013(6) -0.0001(7) C13 0.0392(11) 0.0432(12) 0.0299(10) -0.0105(8) -0.0115(8) 0.0190(9) C14 0.0418(11) 0.0429(12) 0.0255(9) -0.0122(8) -0.0084(8) 0.0141(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 C2 1.393(3) . ? C1 C6 1.395(2) . ? C1 C9 1.488(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 O1 1.375(2) . ? C3 C4 1.389(3) . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 O2 1.367(2) . ? C5 C6 1.388(2) . ? C6 H6 0.9500 . ? O1 C7 1.424(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O2 C8 1.422(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.387(2) . ? C9 C14 1.390(3) . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 C12 1.491(3) 3_574 ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 C6 118.91(15) . . ? C2 C1 C9 120.25(16) . . ? C6 C1 C9 120.84(16) . . ? C3 C2 C1 120.22(17) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? O1 C3 C2 115.51(17) . . ? O1 C3 C4 123.23(15) . . ? C2 C3 C4 121.26(17) . . ? C5 C4 C3 118.25(15) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? O2 C5 C4 123.57(15) . . ? O2 C5 C6 115.19(16) . . ? C4 C5 C6 121.24(17) . . ? C5 C6 C1 120.12(17) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C3 O1 C7 117.21(15) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 O2 C8 117.81(15) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 117.20(15) . . ? C10 C9 C1 121.01(16) . . ? C14 C9 C1 121.79(16) . . ? C11 C10 C9 121.48(17) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 121.66(17) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 116.65(15) . . ? C11 C12 C12 121.5(2) . 3_574 ? C13 C12 C12 121.9(2) . 3_574 ? C14 C13 C12 121.89(18) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C9 121.12(17) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.307 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 934387'