# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_6m #TrackingRef 'scif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (6Z,16E)-2,9-Dioxa-17-methoxycarbonyltricyclo[17.3.0.010,15]docosane-1(19),6,10(15),11,13,16-hexaen-20-one ; _chemical_name_common macrocycle _chemical_melting_point 397(2) _chemical_formula_moiety 'C22 H24 O5' _chemical_formula_sum 'C22 H24 O5' _chemical_formula_weight 368.41 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6741(9) _cell_length_b 9.1126(9) _cell_length_c 12.8419(11) _cell_angle_alpha 96.627(7) _cell_angle_beta 102.887(8) _cell_angle_gamma 106.395(9) _cell_volume 931.84(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1556 _cell_measurement_theta_min 2.8671 _cell_measurement_theta_max 29.0752 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9640 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5802 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3177 _reflns_number_gt 2233 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3177 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1042 _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 O1 O 1.02732(17) 0.19516(14) 0.12439(11) 0.0517(4) Uani 1 1 d . . . O2 O 0.83443(19) 0.02004(13) 0.37625(11) 0.0544(4) Uani 1 1 d . . . O4 O 0.48400(19) -0.37706(18) 0.11430(13) 0.0703(5) Uani 1 1 d . . . C6 C 1.0513(2) -0.0448(2) 0.15789(14) 0.0386(5) Uani 1 1 d . . . C8 C 0.7632(2) -0.21346(19) 0.15133(14) 0.0365(4) Uani 1 1 d . . . C7 C 0.8695(2) -0.10857(19) 0.11500(14) 0.0388(5) Uani 1 1 d . . . H7 H 0.8227 -0.0714 0.0553 0.047 Uiso 1 1 calc R . . C10 C 0.7241(2) -0.2526(2) 0.33534(14) 0.0372(5) Uani 1 1 d . . . O5 O 0.54103(18) -0.19046(18) 0.01860(12) 0.0725(5) Uani 1 1 d . . . C9 C 0.8088(2) -0.2832(2) 0.24975(14) 0.0406(5) Uani 1 1 d . . . H9A H 0.7804 -0.3949 0.2269 0.049 Uiso 1 1 calc R . . H9B H 0.9286 -0.2415 0.2812 0.049 Uiso 1 1 calc R . . C1 C 1.1301(2) 0.1138(2) 0.16322(15) 0.0421(5) Uani 1 1 d . . . O3 O 0.5976(2) -0.51334(16) 0.35208(12) 0.0674(5) Uani 1 1 d . . . C21 C 0.5830(3) -0.2706(2) 0.09422(16) 0.0461(5) Uani 1 1 d . . . C5 C 1.1511(3) -0.1354(2) 0.18824(16) 0.0480(5) Uani 1 1 d . . . H5 H 1.1016 -0.2420 0.1818 0.058 Uiso 1 1 calc R . . C14 C 0.7392(2) -0.1148(2) 0.39251(15) 0.0409(5) Uani 1 1 d . . . C11 C 0.6220(3) -0.3739(2) 0.37688(16) 0.0482(5) Uani 1 1 d . . . C2 C 1.3008(3) 0.1788(2) 0.20549(17) 0.0526(6) Uani 1 1 d . . . H2 H 1.3517 0.2852 0.2120 0.063 Uiso 1 1 calc R . . C4 C 1.3222(3) -0.0721(3) 0.22788(18) 0.0576(6) Uani 1 1 d . . . H4 H 1.3872 -0.1352 0.2474 0.069 Uiso 1 1 calc R . . C17 C 0.9416(3) 0.3395(2) 0.31980(17) 0.0529(6) Uani 1 1 d . . . H17A H 0.9026 0.2515 0.2597 0.064 Uiso 1 1 calc R . . H17B H 0.8496 0.3793 0.3223 0.064 Uiso 1 1 calc R . . C15 C 0.8633(3) 0.1614(2) 0.45022(16) 0.0592(6) Uani 1 1 d . . . H15A H 0.8998 0.1486 0.5247 0.071 Uiso 1 1 calc R . . H15B H 0.7616 0.1888 0.4416 0.071 Uiso 1 1 calc R . . C16 C 0.9958(3) 0.2864(2) 0.42441(17) 0.0597(6) Uani 1 1 d . . . H16A H 1.0887 0.2484 0.4212 0.072 Uiso 1 1 calc R . . H16B H 1.0359 0.3757 0.4836 0.072 Uiso 1 1 calc R . . C3 C 1.3949(3) 0.0849(3) 0.23794(17) 0.0591(6) Uani 1 1 d . . . H3 H 1.5096 0.1289 0.2671 0.071 Uiso 1 1 calc R . . C20 C 1.1001(3) 0.3529(2) 0.11691(19) 0.0625(6) Uani 1 1 d . . . H20A H 1.0212 0.3812 0.0632 0.075 Uiso 1 1 calc R . . H20B H 1.1980 0.3608 0.0906 0.075 Uiso 1 1 calc R . . C13 C 0.6419(3) -0.1250(2) 0.47505(17) 0.0591(6) Uani 1 1 d . . . H13A H 0.5607 -0.0702 0.4607 0.071 Uiso 1 1 calc R . . H13B H 0.7148 -0.0823 0.5480 0.071 Uiso 1 1 calc R . . C18 C 1.0813(3) 0.4634(2) 0.3012(2) 0.0623(6) Uani 1 1 d . . . H18 H 1.1272 0.5518 0.3560 0.075 Uiso 1 1 calc R . . C19 C 1.1496(3) 0.4676(2) 0.2200(2) 0.0614(6) Uani 1 1 d . . . H19 H 1.2419 0.5544 0.2280 0.074 Uiso 1 1 calc R . . C12 C 0.5569(3) -0.2990(2) 0.46067(18) 0.0637(7) Uani 1 1 d . . . H12A H 0.5844 -0.3342 0.5288 0.076 Uiso 1 1 calc R . . H12B H 0.4367 -0.3242 0.4357 0.076 Uiso 1 1 calc R . . C22 C 0.3692(3) -0.2418(4) -0.0432(2) 0.0959(10) Uani 1 1 d . . . H22A H 0.3429 -0.3426 -0.0874 0.144 Uiso 1 1 calc R . . H22B H 0.3505 -0.1689 -0.0889 0.144 Uiso 1 1 calc R . . H22C H 0.2992 -0.2484 0.0056 0.144 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0503(9) 0.0416(8) 0.0584(9) 0.0135(6) 0.0119(7) 0.0079(7) O2 0.0800(11) 0.0381(7) 0.0461(9) 0.0053(6) 0.0261(8) 0.0142(7) O4 0.0472(10) 0.0748(10) 0.0703(11) 0.0186(8) 0.0118(8) -0.0082(8) C6 0.0372(11) 0.0418(11) 0.0339(11) 0.0047(8) 0.0123(8) 0.0068(9) C8 0.0388(11) 0.0387(10) 0.0307(11) 0.0018(7) 0.0124(8) 0.0099(8) C7 0.0407(12) 0.0423(10) 0.0311(11) 0.0049(8) 0.0092(8) 0.0110(9) C10 0.0365(11) 0.0420(10) 0.0336(11) 0.0100(8) 0.0104(8) 0.0116(8) O5 0.0399(9) 0.1047(12) 0.0592(11) 0.0344(9) -0.0013(7) 0.0060(8) C9 0.0423(12) 0.0421(10) 0.0403(12) 0.0093(8) 0.0151(9) 0.0142(9) C1 0.0426(12) 0.0451(11) 0.0364(11) 0.0064(8) 0.0142(9) 0.0083(10) O3 0.0763(12) 0.0491(9) 0.0672(11) 0.0122(7) 0.0268(9) -0.0012(8) C21 0.0430(13) 0.0541(12) 0.0343(12) 0.0024(9) 0.0109(9) 0.0070(10) C5 0.0456(13) 0.0485(11) 0.0520(13) 0.0094(9) 0.0190(10) 0.0134(10) C14 0.0437(12) 0.0466(11) 0.0343(11) 0.0111(8) 0.0105(9) 0.0159(9) C11 0.0433(13) 0.0525(13) 0.0424(13) 0.0097(9) 0.0117(9) 0.0050(10) C2 0.0430(13) 0.0532(12) 0.0516(14) 0.0046(10) 0.0129(10) 0.0017(11) C4 0.0467(14) 0.0701(15) 0.0617(15) 0.0149(11) 0.0181(11) 0.0237(12) C17 0.0486(13) 0.0527(12) 0.0579(15) 0.0118(10) 0.0104(10) 0.0192(10) C15 0.0878(18) 0.0470(12) 0.0396(13) -0.0007(9) 0.0139(12) 0.0225(12) C16 0.0687(16) 0.0416(11) 0.0558(15) 0.0001(10) -0.0017(11) 0.0154(11) C3 0.0337(12) 0.0789(16) 0.0536(15) 0.0041(11) 0.0093(10) 0.0060(12) C20 0.0646(16) 0.0478(12) 0.0722(17) 0.0247(11) 0.0175(12) 0.0087(11) C13 0.0701(16) 0.0736(15) 0.0483(14) 0.0143(11) 0.0299(12) 0.0339(12) C18 0.0569(15) 0.0401(11) 0.0866(19) 0.0038(11) 0.0196(13) 0.0132(10) C19 0.0551(15) 0.0395(12) 0.0917(19) 0.0159(11) 0.0262(14) 0.0117(10) C12 0.0525(14) 0.0822(16) 0.0553(15) 0.0144(12) 0.0273(11) 0.0091(12) C22 0.0437(16) 0.152(3) 0.0713(19) 0.0359(17) -0.0069(13) 0.0114(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.362(2) . ? O1 C20 1.422(2) . ? O2 C14 1.341(2) . ? O2 C15 1.433(2) . ? O4 C21 1.196(2) . ? C6 C5 1.382(3) . ? C6 C1 1.400(2) . ? C6 C7 1.466(2) . ? C8 C7 1.334(2) . ? C8 C21 1.481(3) . ? C8 C9 1.504(2) . ? C7 H7 0.9300 . ? C10 C14 1.335(2) . ? C10 C11 1.444(2) . ? C10 C9 1.494(2) . ? O5 C21 1.329(2) . ? O5 C22 1.436(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C1 C2 1.382(3) . ? O3 C11 1.219(2) . ? C5 C4 1.381(3) . ? C5 H5 0.9300 . ? C14 C13 1.491(3) . ? C11 C12 1.504(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C4 C3 1.368(3) . ? C4 H4 0.9300 . ? C17 C18 1.489(3) . ? C17 C16 1.502(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C15 C16 1.498(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C3 H3 0.9300 . ? C20 C19 1.484(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C13 C12 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C18 C19 1.308(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C20 118.49(16) . . ? C14 O2 C15 119.18(14) . . ? C5 C6 C1 117.70(18) . . ? C5 C6 C7 123.18(16) . . ? C1 C6 C7 119.02(18) . . ? C7 C8 C21 120.37(18) . . ? C7 C8 C9 125.52(17) . . ? C21 C8 C9 114.11(15) . . ? C8 C7 C6 127.75(18) . . ? C8 C7 H7 116.1 . . ? C6 C7 H7 116.1 . . ? C14 C10 C11 108.53(16) . . ? C14 C10 C9 127.54(15) . . ? C11 C10 C9 123.69(16) . . ? C21 O5 C22 116.70(17) . . ? C10 C9 C8 113.83(16) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O1 C1 C2 123.97(17) . . ? O1 C1 C6 115.33(17) . . ? C2 C1 C6 120.7(2) . . ? O4 C21 O5 122.94(19) . . ? O4 C21 C8 123.85(19) . . ? O5 C21 C8 113.21(16) . . ? C4 C5 C6 121.85(18) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C10 C14 O2 122.29(16) . . ? C10 C14 C13 114.16(16) . . ? O2 C14 C13 123.55(16) . . ? O3 C11 C10 126.16(19) . . ? O3 C11 C12 125.30(18) . . ? C10 C11 C12 108.47(17) . . ? C3 C2 C1 119.49(18) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C18 C17 C16 111.20(18) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O2 C15 C16 107.37(17) . . ? O2 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? O2 C15 H15B 110.2 . . ? C16 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C15 C16 C17 115.13(18) . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? O1 C20 C19 115.25(18) . . ? O1 C20 H20A 108.5 . . ? C19 C20 H20A 108.5 . . ? O1 C20 H20B 108.5 . . ? C19 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C14 C13 C12 102.98(16) . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? C19 C18 C17 130.2(2) . . ? C19 C18 H18 114.9 . . ? C17 C18 H18 114.9 . . ? C18 C19 C20 129.0(2) . . ? C18 C19 H19 115.5 . . ? C20 C19 H19 115.5 . . ? C11 C12 C13 105.51(16) . . ? C11 C12 H12A 110.6 . . ? C13 C12 H12A 110.6 . . ? C11 C12 H12B 110.6 . . ? C13 C12 H12B 110.6 . . ? H12A C12 H12B 108.8 . . ? O5 C22 H22A 109.5 . . ? O5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.176 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 915410' ####################################################################### # # 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_global data_6a #TrackingRef 'sf 1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4E,15E)-10,10-Dimethyl-2,7-dioxa-15-methoxycarbonyltricyclo [15.4.0.08,13]henicosane-1(17),4,8(13),15,18,20-hexaen-12-one ; _chemical_name_common macrocycle _chemical_melting_point 419(2) _chemical_formula_moiety 'C23 H26 O5' _chemical_formula_sum 'C23 H26 O5' _chemical_formula_weight 382.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6354(9) _cell_length_b 10.1017(7) _cell_length_c 15.6517(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.2200(10) _cell_angle_gamma 90.00 _cell_volume 1989.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2578 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 22.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max .20 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3124 _exptl_absorpt_correction_T_max 0.5177 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14897 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.94 _reflns_number_total 3866 _reflns_number_gt 3054 _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^)+(0.0579P)^2^+1.0166P] 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 3866 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1257 _refine_ls_R_factor_gt 0.0975 _refine_ls_wR_factor_ref 0.1945 _refine_ls_wR_factor_gt 0.1821 _refine_ls_goodness_of_fit_ref 1.289 _refine_ls_restrained_S_all 1.289 _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 O2 O 0.19473(18) 0.1986(2) 0.71689(13) 0.0468(7) Uani 1 1 d . . . C10 C 0.2842(3) 0.1991(3) 0.59745(19) 0.0345(8) Uani 1 1 d . . . O1 O -0.1150(2) 0.4171(2) 0.70873(15) 0.0534(7) Uani 1 1 d . . . C15 C 0.2867(2) 0.1757(3) 0.68239(19) 0.0325(7) Uani 1 1 d . . . O3 O 0.3777(2) 0.1759(3) 0.47512(16) 0.0689(9) Uani 1 1 d . . . O5 O 0.2852(2) 0.4770(3) 0.52066(17) 0.0627(8) Uani 1 1 d . . . C11 C 0.3779(3) 0.1678(3) 0.5531(2) 0.0418(8) Uani 1 1 d . . . C7 C 0.0389(3) 0.3953(3) 0.5899(2) 0.0392(8) Uani 1 1 d . . . H7 H 0.0238 0.4819 0.6048 0.047 Uiso 1 1 calc R . . C6 C -0.0496(3) 0.3015(3) 0.5907(2) 0.0397(8) Uani 1 1 d . . . C8 C 0.1378(3) 0.3732(3) 0.57074(19) 0.0357(8) Uani 1 1 d . . . O4 O 0.2016(2) 0.5865(3) 0.6180(2) 0.0722(9) Uani 1 1 d . . . C9 C 0.1834(3) 0.2417(3) 0.5461(2) 0.0387(8) Uani 1 1 d . . . H9A H 0.1300 0.1740 0.5514 0.046 Uiso 1 1 calc R . . H9B H 0.1970 0.2459 0.4861 0.046 Uiso 1 1 calc R . . C14 C 0.3784(3) 0.1195(3) 0.7369(2) 0.0406(8) Uani 1 1 d . . . H14A H 0.3521 0.0613 0.7795 0.049 Uiso 1 1 calc R . . H14B H 0.4172 0.1909 0.7670 0.049 Uiso 1 1 calc R . . C16 C 0.1906(3) 0.2185(4) 0.8073(2) 0.0478(9) Uani 1 1 d . . . H16A H 0.2350 0.2925 0.8275 0.057 Uiso 1 1 calc R . . H16B H 0.2137 0.1398 0.8392 0.057 Uiso 1 1 calc R . . C12 C 0.4766(3) 0.1261(4) 0.6072(2) 0.0452(9) Uani 1 1 d . . . H12A H 0.5154 0.2047 0.6272 0.054 Uiso 1 1 calc R . . H12B H 0.5215 0.0762 0.5719 0.054 Uiso 1 1 calc R . . C20 C 0.2099(3) 0.4900(4) 0.5747(2) 0.0457(9) Uani 1 1 d . . . C13 C 0.4542(3) 0.0419(3) 0.6848(2) 0.0384(8) Uani 1 1 d . . . C1 C -0.1211(3) 0.3099(4) 0.6537(2) 0.0432(9) Uani 1 1 d . . . C2 C -0.2003(3) 0.2181(4) 0.6581(3) 0.0562(11) Uani 1 1 d . . . H2 H -0.2452 0.2236 0.7018 0.067 Uiso 1 1 calc R . . C5 C -0.0684(3) 0.2025(4) 0.5293(2) 0.0471(9) Uani 1 1 d . . . H5 H -0.0252 0.1973 0.4844 0.057 Uiso 1 1 calc R . . C17 C 0.0763(3) 0.2470(4) 0.8163(2) 0.0564(11) Uani 1 1 d . . . H17 H 0.0335 0.1775 0.8315 0.068 Uiso 1 1 calc R . . C4 C -0.1490(3) 0.1124(4) 0.5332(3) 0.0547(10) Uani 1 1 d . . . H4 H -0.1596 0.0473 0.4913 0.066 Uiso 1 1 calc R . . C19 C -0.0814(3) 0.3876(4) 0.7974(2) 0.0622(12) Uani 1 1 d . . . H19A H -0.1193 0.3108 0.8160 0.075 Uiso 1 1 calc R . . H19B H -0.0965 0.4620 0.8335 0.075 Uiso 1 1 calc R . . C3 C -0.2140(3) 0.1181(4) 0.5988(3) 0.0589(11) Uani 1 1 d . . . H3 H -0.2668 0.0549 0.6030 0.071 Uiso 1 1 calc R . . C22 C 0.5580(3) 0.0132(4) 0.7405(3) 0.0580(11) Uani 1 1 d . . . H22A H 0.5907 0.0952 0.7594 0.087 Uiso 1 1 calc R . . H22B H 0.6054 -0.0352 0.7075 0.087 Uiso 1 1 calc R . . H22C H 0.5428 -0.0383 0.7895 0.087 Uiso 1 1 calc R . . C18 C 0.0336(4) 0.3610(5) 0.8045(2) 0.0647(12) Uani 1 1 d . . . H18 H 0.0788 0.4329 0.8000 0.078 Uiso 1 1 calc R . . C23 C 0.4048(3) -0.0895(4) 0.6547(3) 0.0550(10) Uani 1 1 d . . . H23A H 0.3891 -0.1409 0.7037 0.083 Uiso 1 1 calc R . . H23B H 0.4538 -0.1373 0.6228 0.083 Uiso 1 1 calc R . . H23C H 0.3404 -0.0733 0.6188 0.083 Uiso 1 1 calc R . . C21 C 0.3561(4) 0.5870(5) 0.5146(3) 0.0818(15) Uani 1 1 d . . . H21A H 0.3157 0.6657 0.5006 0.123 Uiso 1 1 calc R . . H21B H 0.4025 0.5698 0.4705 0.123 Uiso 1 1 calc R . . H21C H 0.3976 0.5990 0.5685 0.123 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 O2 0.0470(14) 0.0654(17) 0.0290(12) 0.0044(11) 0.0086(10) 0.0145(12) C10 0.0390(19) 0.0317(18) 0.0329(17) -0.0016(14) 0.0030(14) 0.0035(15) O1 0.0670(18) 0.0509(16) 0.0439(14) -0.0017(12) 0.0132(13) 0.0213(13) C15 0.0354(18) 0.0263(17) 0.0364(18) -0.0029(13) 0.0063(14) -0.0012(14) O3 0.0653(19) 0.107(2) 0.0367(15) 0.0074(15) 0.0187(13) 0.0316(17) O5 0.0643(19) 0.0531(17) 0.0740(19) 0.0113(14) 0.0238(16) -0.0016(14) C11 0.047(2) 0.039(2) 0.041(2) 0.0004(16) 0.0096(16) 0.0067(16) C7 0.051(2) 0.0333(19) 0.0330(17) 0.0000(14) 0.0031(15) 0.0145(16) C6 0.043(2) 0.038(2) 0.0372(18) 0.0014(15) 0.0025(15) 0.0155(16) C8 0.046(2) 0.0357(19) 0.0248(16) 0.0038(14) 0.0018(14) 0.0097(16) O4 0.080(2) 0.0516(18) 0.086(2) -0.0143(16) 0.0130(17) -0.0047(16) C9 0.046(2) 0.043(2) 0.0277(16) -0.0025(14) 0.0042(15) 0.0067(16) C14 0.045(2) 0.041(2) 0.0342(18) 0.0009(15) -0.0050(15) 0.0039(16) C16 0.053(2) 0.061(3) 0.0294(18) -0.0054(17) 0.0061(16) 0.0027(19) C12 0.0338(19) 0.054(2) 0.049(2) 0.0023(17) 0.0110(16) 0.0016(17) C20 0.054(2) 0.041(2) 0.041(2) 0.0097(17) -0.0008(17) 0.0115(18) C13 0.0326(18) 0.037(2) 0.0445(19) 0.0002(15) 0.0000(15) 0.0013(15) C1 0.041(2) 0.047(2) 0.042(2) 0.0051(17) 0.0037(16) 0.0179(17) C2 0.047(2) 0.065(3) 0.058(2) 0.004(2) 0.0133(19) 0.011(2) C5 0.044(2) 0.061(3) 0.0366(19) -0.0055(17) 0.0020(16) 0.0114(19) C17 0.082(3) 0.052(3) 0.038(2) -0.0001(18) 0.019(2) 0.001(2) C4 0.051(2) 0.051(2) 0.060(2) -0.0079(19) -0.006(2) 0.006(2) C19 0.075(3) 0.067(3) 0.046(2) -0.005(2) 0.011(2) 0.025(2) C3 0.043(2) 0.062(3) 0.071(3) 0.007(2) 0.001(2) 0.001(2) C22 0.042(2) 0.060(3) 0.070(3) 0.010(2) -0.006(2) 0.0043(19) C18 0.088(3) 0.056(3) 0.049(2) -0.010(2) 0.004(2) 0.003(2) C23 0.051(2) 0.044(2) 0.070(3) -0.0039(19) 0.001(2) 0.0048(18) C21 0.073(3) 0.074(3) 0.100(4) 0.029(3) 0.018(3) -0.011(3) _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 O2 C15 1.346(4) . ? O2 C16 1.434(4) . ? C10 C15 1.348(4) . ? C10 C11 1.460(4) . ? C10 C9 1.506(4) . ? O1 C1 1.381(4) . ? O1 C19 1.445(4) . ? C15 C14 1.487(4) . ? O3 C11 1.224(4) . ? O5 C20 1.335(4) . ? O5 C21 1.436(5) . ? C11 C12 1.502(5) . ? C7 C8 1.331(4) . ? C7 C6 1.466(5) . ? C6 C5 1.392(5) . ? C6 C1 1.400(5) . ? C8 C20 1.489(5) . ? C8 C9 1.511(4) . ? O4 C20 1.197(4) . ? C14 C13 1.529(4) . ? C16 C17 1.491(5) . ? C12 C13 1.530(5) . ? C13 C23 1.523(5) . ? C13 C22 1.535(5) . ? C1 C2 1.370(5) . ? C2 C3 1.371(5) . ? C5 C4 1.371(5) . ? C17 C18 1.278(5) . ? C4 C3 1.373(5) . ? C19 C18 1.472(6) . ? 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 C15 O2 C16 122.0(3) . . ? C15 C10 C11 118.9(3) . . ? C15 C10 C9 121.3(3) . . ? C11 C10 C9 119.4(3) . . ? C1 O1 C19 115.6(3) . . ? O2 C15 C10 114.9(3) . . ? O2 C15 C14 119.5(3) . . ? C10 C15 C14 125.5(3) . . ? C20 O5 C21 116.8(3) . . ? O3 C11 C10 122.1(3) . . ? O3 C11 C12 120.5(3) . . ? C10 C11 C12 117.4(3) . . ? C8 C7 C6 128.7(3) . . ? C5 C6 C1 116.6(3) . . ? C5 C6 C7 122.8(3) . . ? C1 C6 C7 120.5(3) . . ? C7 C8 C20 116.2(3) . . ? C7 C8 C9 126.4(3) . . ? C20 C8 C9 117.5(3) . . ? C10 C9 C8 116.0(3) . . ? C15 C14 C13 112.5(3) . . ? O2 C16 C17 104.1(3) . . ? C11 C12 C13 113.5(3) . . ? O4 C20 O5 122.9(4) . . ? O4 C20 C8 125.8(3) . . ? O5 C20 C8 111.3(3) . . ? C23 C13 C14 110.7(3) . . ? C23 C13 C12 109.9(3) . . ? C14 C13 C12 108.0(3) . . ? C23 C13 C22 108.4(3) . . ? C14 C13 C22 109.8(3) . . ? C12 C13 C22 110.2(3) . . ? C2 C1 O1 119.9(3) . . ? C2 C1 C6 121.0(3) . . ? O1 C1 C6 119.0(3) . . ? C1 C2 C3 120.9(4) . . ? C4 C5 C6 121.9(3) . . ? C18 C17 C16 124.0(4) . . ? C5 C4 C3 120.2(4) . . ? O1 C19 C18 108.2(3) . . ? C2 C3 C4 119.3(4) . . ? C17 C18 C19 125.2(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.418 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 914817' ####################################################################### # # 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_global #===END data_6c-E #TrackingRef 'sf 1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4E,14E)-2,7-Dioxa-15-methoxycarbonyltricyclo[15.3.0.08,13] icosane-1(17),4,8(13),9,11,14-hexaen- 18-one ; _chemical_name_common macrocycle _chemical_melting_point 415(2) _chemical_formula_moiety 'C20 H20 O5' _chemical_formula_sum 'C20 H20 O5' _chemical_formula_weight 340.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5864(7) _cell_length_b 12.2835(9) _cell_length_c 14.5863(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.9790(10) _cell_angle_gamma 90.00 _cell_volume 1701.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2620 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 20.78 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17357 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.06 _reflns_number_total 3353 _reflns_number_gt 2186 _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^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3353 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O2 O 0.17912(16) 0.60781(12) 0.96313(10) 0.0549(4) Uani 1 1 d . . . O5 O 0.31626(16) 0.97709(13) 1.01784(10) 0.0635(5) Uani 1 1 d . . . O1 O 0.33145(18) 0.81296(14) 0.73543(11) 0.0676(5) Uani 1 1 d . . . O4 O 0.16794(18) 0.92257(15) 1.11203(11) 0.0735(5) Uani 1 1 d . . . C19 C 0.2027(2) 0.92307(17) 1.03638(15) 0.0473(5) Uani 1 1 d . . . C14 C 0.0459(2) 0.61229(17) 0.92107(13) 0.0457(5) Uani 1 1 d . . . C7 C 0.1684(2) 0.87552(17) 0.87283(14) 0.0472(5) Uani 1 1 d . . . H7 H 0.2529 0.9127 0.8730 0.057 Uiso 1 1 calc R . . C6 C 0.1036(2) 0.83586(17) 0.78195(15) 0.0484(6) Uani 1 1 d . . . C8 C 0.1242(2) 0.86618(16) 0.95507(14) 0.0436(5) Uani 1 1 d . . . C9 C -0.0009(2) 0.80280(17) 0.98017(16) 0.0535(6) Uani 1 1 d . . . H9A H 0.0163 0.7874 1.0460 0.064 Uiso 1 1 calc R . . H9B H -0.0830 0.8497 0.9696 0.064 Uiso 1 1 calc R . . C10 C -0.0370(2) 0.69787(17) 0.93054(14) 0.0445(5) Uani 1 1 d . . . C1 C 0.1870(3) 0.80297(18) 0.71596(15) 0.0537(6) Uani 1 1 d . . . O3 O -0.28215(19) 0.72816(16) 0.88905(15) 0.0888(6) Uani 1 1 d . . . C5 C -0.0420(3) 0.83712(17) 0.75626(16) 0.0564(6) Uani 1 1 d . . . H5 H -0.0997 0.8620 0.7981 0.068 Uiso 1 1 calc R . . C11 C -0.1779(3) 0.67124(19) 0.88796(16) 0.0559(6) Uani 1 1 d . . . C13 C -0.0265(3) 0.52175(18) 0.86383(16) 0.0592(6) Uani 1 1 d . . . H13A H -0.0215 0.4540 0.8983 0.071 Uiso 1 1 calc R . . H13B H 0.0148 0.5110 0.8074 0.071 Uiso 1 1 calc R . . C12 C -0.1775(3) 0.56182(19) 0.84264(16) 0.0645(7) Uani 1 1 d . . . H12A H -0.2057 0.5679 0.7764 0.077 Uiso 1 1 calc R . . H12B H -0.2414 0.5124 0.8679 0.077 Uiso 1 1 calc R . . C3 C -0.0184(3) 0.7664(2) 0.60742(18) 0.0737(8) Uani 1 1 d . . . H3 H -0.0593 0.7415 0.5497 0.088 Uiso 1 1 calc R . . C15 C 0.2759(3) 0.5330(2) 0.92672(18) 0.0682(7) Uani 1 1 d . . . H15A H 0.2329 0.4616 0.9176 0.082 Uiso 1 1 calc R . . H15B H 0.3615 0.5259 0.9704 0.082 Uiso 1 1 calc R . . C4 C -0.1022(3) 0.8023(2) 0.66998(19) 0.0673(7) Uani 1 1 d . . . H4 H -0.1996 0.8031 0.6543 0.081 Uiso 1 1 calc R . . C18 C 0.4104(3) 0.7117(2) 0.74035(19) 0.0784(8) Uani 1 1 d . . . H18A H 0.5094 0.7267 0.7391 0.094 Uiso 1 1 calc R . . H18B H 0.3766 0.6661 0.6876 0.094 Uiso 1 1 calc R . . C2 C 0.1262(3) 0.76719(19) 0.62952(17) 0.0684(7) Uani 1 1 d . . . H2 H 0.1828 0.7437 0.5865 0.082 Uiso 1 1 calc R . . C16 C 0.3101(3) 0.5763(2) 0.8361(2) 0.0740(8) Uani 1 1 d . . . H16 H 0.2677 0.5427 0.7822 0.089 Uiso 1 1 calc R . . C20 C 0.4013(3) 1.0288(2) 1.09532(17) 0.0724(8) Uani 1 1 d . . . H20A H 0.3421 1.0724 1.1287 0.109 Uiso 1 1 calc R . . H20B H 0.4707 1.0743 1.0730 0.109 Uiso 1 1 calc R . . H20C H 0.4474 0.9741 1.1357 0.109 Uiso 1 1 calc R . . C17 C 0.3916(3) 0.6545(3) 0.8276(2) 0.0823(8) Uani 1 1 d . . . H17 H 0.4457 0.6793 0.8814 0.099 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 O2 0.0569(10) 0.0590(10) 0.0484(9) 0.0006(7) 0.0058(8) 0.0115(8) O5 0.0591(11) 0.0784(11) 0.0529(10) -0.0154(8) 0.0081(8) -0.0200(9) O1 0.0653(12) 0.0785(12) 0.0621(11) -0.0064(9) 0.0199(9) -0.0189(10) O4 0.0746(12) 0.0980(13) 0.0500(10) -0.0183(10) 0.0160(9) -0.0171(10) C19 0.0459(13) 0.0490(13) 0.0471(14) -0.0033(11) 0.0066(11) 0.0059(11) C14 0.0553(14) 0.0494(13) 0.0329(11) 0.0083(10) 0.0075(10) -0.0019(11) C7 0.0448(13) 0.0478(13) 0.0478(13) 0.0017(10) 0.0019(10) -0.0030(10) C6 0.0549(14) 0.0455(13) 0.0434(13) 0.0066(10) 0.0021(11) -0.0087(10) C8 0.0413(12) 0.0418(12) 0.0470(13) -0.0018(10) 0.0038(10) 0.0056(10) C9 0.0485(14) 0.0565(14) 0.0578(14) -0.0091(12) 0.0152(11) 0.0001(11) C10 0.0477(13) 0.0466(12) 0.0402(12) 0.0022(10) 0.0101(10) -0.0032(11) C1 0.0641(16) 0.0542(14) 0.0426(13) 0.0044(11) 0.0072(12) -0.0169(12) O3 0.0481(11) 0.0875(14) 0.1288(18) -0.0114(12) 0.0049(11) -0.0023(10) C5 0.0617(16) 0.0506(14) 0.0533(15) 0.0088(11) -0.0043(12) -0.0024(11) C11 0.0522(16) 0.0580(15) 0.0577(15) 0.0064(12) 0.0085(12) -0.0033(13) C13 0.0836(19) 0.0473(13) 0.0465(13) 0.0017(11) 0.0085(12) -0.0052(12) C12 0.0744(19) 0.0634(16) 0.0536(15) 0.0018(12) 0.0019(13) -0.0179(13) C3 0.099(2) 0.0655(17) 0.0502(16) 0.0030(13) -0.0139(16) -0.0252(16) C15 0.0706(18) 0.0622(16) 0.0737(18) 0.0076(13) 0.0164(14) 0.0223(13) C4 0.0708(18) 0.0593(16) 0.0645(18) 0.0100(13) -0.0164(15) -0.0053(13) C18 0.0635(18) 0.107(2) 0.0701(18) -0.0015(17) 0.0282(14) -0.0068(16) C2 0.096(2) 0.0629(16) 0.0472(14) -0.0023(12) 0.0131(14) -0.0206(15) C16 0.076(2) 0.0673(18) 0.083(2) -0.0080(15) 0.0269(16) 0.0135(15) C20 0.0640(17) 0.0826(18) 0.0682(17) -0.0247(14) 0.0007(14) -0.0135(14) C17 0.0636(18) 0.105(2) 0.079(2) -0.0026(18) 0.0122(15) -0.0020(17) _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 O2 C14 1.339(2) . ? O2 C15 1.457(3) . ? O5 C19 1.335(3) . ? O5 C20 1.445(3) . ? O1 C1 1.380(3) . ? O1 C18 1.453(3) . ? O4 C19 1.196(2) . ? C19 C8 1.488(3) . ? C14 C10 1.336(3) . ? C14 C13 1.502(3) . ? C7 C8 1.332(3) . ? C7 C6 1.467(3) . ? C7 H7 0.9300 . ? C6 C1 1.394(3) . ? C6 C5 1.394(3) . ? C8 C9 1.517(3) . ? C9 C10 1.495(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.444(3) . ? C1 C2 1.385(3) . ? O3 C11 1.221(3) . ? C5 C4 1.378(3) . ? C5 H5 0.9300 . ? C11 C12 1.498(3) . ? C13 C12 1.519(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C3 C4 1.369(4) . ? C3 C2 1.379(4) . ? C3 H3 0.9300 . ? C15 C16 1.503(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C4 H4 0.9300 . ? C18 C17 1.485(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C2 H2 0.9300 . ? C16 C17 1.255(4) . ? C16 H16 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O2 C15 118.28(18) . . ? C19 O5 C20 116.58(18) . . ? C1 O1 C18 115.77(19) . . ? O4 C19 O5 121.9(2) . . ? O4 C19 C8 123.9(2) . . ? O5 C19 C8 114.12(19) . . ? C10 C14 O2 121.9(2) . . ? C10 C14 C13 113.9(2) . . ? O2 C14 C13 124.2(2) . . ? C8 C7 C6 129.6(2) . . ? C8 C7 H7 115.2 . . ? C6 C7 H7 115.2 . . ? C1 C6 C5 117.8(2) . . ? C1 C6 C7 120.6(2) . . ? C5 C6 C7 121.5(2) . . ? C7 C8 C19 119.25(19) . . ? C7 C8 C9 128.5(2) . . ? C19 C8 C9 112.22(18) . . ? C10 C9 C8 117.58(17) . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9B 107.9 . . ? C8 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? C14 C10 C11 108.1(2) . . ? C14 C10 C9 128.9(2) . . ? C11 C10 C9 122.9(2) . . ? O1 C1 C2 119.9(2) . . ? O1 C1 C6 119.2(2) . . ? C2 C1 C6 120.8(2) . . ? C4 C5 C6 121.2(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? O3 C11 C10 125.7(2) . . ? O3 C11 C12 124.9(2) . . ? C10 C11 C12 109.5(2) . . ? C14 C13 C12 103.10(19) . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13B 111.1 . . ? C12 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? C11 C12 C13 105.18(19) . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? O2 C15 C16 108.94(19) . . ? O2 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? O2 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? O1 C18 C17 108.8(2) . . ? O1 C18 H18A 109.9 . . ? C17 C18 H18A 109.9 . . ? O1 C18 H18B 109.9 . . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C17 C16 C15 125.0(3) . . ? C17 C16 H16 117.5 . . ? C15 C16 H16 117.5 . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C17 C18 126.7(3) . . ? C16 C17 H17 116.7 . . ? C18 C17 H17 116.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.210 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 914818' ####################################################################### # # 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_global #===END data_6c-Z #TrackingRef 'sf 1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4Z,14E)-2,7-Dioxa-15-methoxycarbonyltricyclo[15.3.0.08,13] icosane-1(17),4,8(13),9,11,14-hexaen-18-one ; _chemical_name_common macrocycle _chemical_melting_point 417(2) _chemical_formula_moiety 'C20 H20 O5' _chemical_formula_sum 'C20 H20 O5' _chemical_formula_weight 340.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.440(6) _cell_length_b 10.579(3) _cell_length_c 7.873(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.119(5) _cell_angle_gamma 90.00 _cell_volume 1701.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3251 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 22.06 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16023 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.17 _reflns_number_total 3026 _reflns_number_gt 2517 _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^)+(0.0484P)^2^+0.4484P] 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 3026 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 O2 O 0.25890(6) 0.52870(13) 0.51519(15) 0.0432(4) Uani 1 1 d . . . O1 O 0.39723(6) 0.35868(12) 0.23403(16) 0.0449(4) Uani 1 1 d . . . C7 C 0.27659(9) 0.45532(17) 0.1015(2) 0.0362(4) Uani 1 1 d . . . H7 H 0.2838 0.3717 0.0709 0.043 Uiso 1 1 calc R . . C6 C 0.33543(9) 0.53394(17) 0.1144(2) 0.0361(4) Uani 1 1 d . . . O5 O 0.10567(7) 0.42612(14) 0.0770(2) 0.0588(4) Uani 1 1 d . . . C8 C 0.21443(9) 0.48476(17) 0.1268(2) 0.0349(4) Uani 1 1 d . . . C1 C 0.39402(9) 0.48222(18) 0.1770(2) 0.0384(4) Uani 1 1 d . . . C10 C 0.16154(9) 0.58802(17) 0.3701(2) 0.0375(4) Uani 1 1 d . . . C16 C 0.36036(9) 0.46466(19) 0.6520(2) 0.0438(5) Uani 1 1 d . . . H16 H 0.3851 0.5071 0.7355 0.053 Uiso 1 1 calc R . . C14 C 0.19410(9) 0.54952(17) 0.5119(2) 0.0367(4) Uani 1 1 d . . . O3 O 0.04992(7) 0.64371(16) 0.3112(2) 0.0676(5) Uani 1 1 d . . . C9 C 0.18974(9) 0.60753(17) 0.1984(2) 0.0400(5) Uani 1 1 d . . . H9A H 0.2255 0.6676 0.2082 0.048 Uiso 1 1 calc R . . H9B H 0.1564 0.6426 0.1213 0.048 Uiso 1 1 calc R . . C19 C 0.16600(10) 0.3819(2) 0.0891(2) 0.0452(5) Uani 1 1 d . . . C13 C 0.15249(10) 0.5347(2) 0.6633(2) 0.0479(5) Uani 1 1 d . . . H13A H 0.1672 0.5900 0.7554 0.058 Uiso 1 1 calc R . . H13B H 0.1528 0.4480 0.7036 0.058 Uiso 1 1 calc R . . C5 C 0.33760(11) 0.65644(19) 0.0482(3) 0.0487(5) Uani 1 1 d . . . H5 H 0.2991 0.6941 0.0070 0.058 Uiso 1 1 calc R . . C17 C 0.39283(10) 0.40561(19) 0.5354(2) 0.0442(5) Uani 1 1 d . . . H17 H 0.4383 0.4102 0.5453 0.053 Uiso 1 1 calc R . . C18 C 0.36493(10) 0.33209(19) 0.3892(2) 0.0438(5) Uani 1 1 d . . . H18A H 0.3688 0.2426 0.4143 0.053 Uiso 1 1 calc R . . H18B H 0.3187 0.3518 0.3739 0.053 Uiso 1 1 calc R . . C15 C 0.28804(10) 0.4707(2) 0.6645(2) 0.0526(5) Uani 1 1 d . . . H15A H 0.2707 0.3860 0.6768 0.063 Uiso 1 1 calc R . . H15B H 0.2771 0.5191 0.7641 0.063 Uiso 1 1 calc R . . C11 C 0.09338(10) 0.60616(19) 0.4094(3) 0.0470(5) Uani 1 1 d . . . C12 C 0.08480(10) 0.5729(2) 0.5934(3) 0.0551(6) Uani 1 1 d . . . H12A H 0.0541 0.5035 0.6032 0.066 Uiso 1 1 calc R . . H12B H 0.0685 0.6450 0.6551 0.066 Uiso 1 1 calc R . . C2 C 0.45184(11) 0.5488(2) 0.1731(3) 0.0566(6) Uani 1 1 d . . . H2 H 0.4905 0.5126 0.2159 0.068 Uiso 1 1 calc R . . O4 O 0.17943(8) 0.27374(16) 0.0660(3) 0.0859(6) Uani 1 1 d . . . C4 C 0.39529(13) 0.7223(2) 0.0429(3) 0.0665(7) Uani 1 1 d . . . H4 H 0.3958 0.8032 -0.0034 0.080 Uiso 1 1 calc R . . C3 C 0.45245(13) 0.6685(3) 0.1062(3) 0.0726(8) Uani 1 1 d . . . H3 H 0.4915 0.7134 0.1036 0.087 Uiso 1 1 calc R . . C20 C 0.05391(12) 0.3363(3) 0.0398(4) 0.0851(9) Uani 1 1 d . . . H20A H 0.0625 0.2928 -0.0641 0.128 Uiso 1 1 calc R . . H20B H 0.0129 0.3801 0.0277 0.128 Uiso 1 1 calc R . . H20C H 0.0520 0.2763 0.1309 0.128 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 O2 0.0361(7) 0.0613(9) 0.0322(7) 0.0056(6) 0.0005(5) 0.0040(6) O1 0.0474(8) 0.0445(8) 0.0431(8) -0.0036(6) 0.0063(6) 0.0084(6) C7 0.0443(11) 0.0348(10) 0.0295(9) -0.0015(7) 0.0020(8) 0.0010(8) C6 0.0432(11) 0.0351(10) 0.0306(9) -0.0046(7) 0.0080(8) -0.0019(8) O5 0.0383(8) 0.0660(10) 0.0718(10) -0.0029(8) -0.0042(7) -0.0080(7) C8 0.0400(11) 0.0374(10) 0.0273(9) 0.0035(7) 0.0002(7) 0.0010(8) C1 0.0423(11) 0.0397(11) 0.0336(10) -0.0088(8) 0.0081(8) -0.0012(8) C10 0.0372(10) 0.0363(10) 0.0390(10) -0.0025(8) 0.0031(8) 0.0027(8) C16 0.0457(12) 0.0475(12) 0.0376(11) 0.0008(9) -0.0072(9) -0.0007(9) C14 0.0375(10) 0.0361(10) 0.0369(10) -0.0047(8) 0.0040(8) -0.0013(8) O3 0.0443(9) 0.0869(12) 0.0715(11) 0.0068(9) 0.0016(8) 0.0222(8) C9 0.0422(11) 0.0395(11) 0.0383(10) 0.0032(8) 0.0008(8) 0.0042(8) C19 0.0438(12) 0.0486(13) 0.0429(11) 0.0020(9) -0.0012(9) -0.0032(9) C13 0.0514(12) 0.0523(12) 0.0408(11) -0.0013(9) 0.0122(9) 0.0018(10) C5 0.0608(13) 0.0431(12) 0.0432(11) 0.0009(9) 0.0158(10) 0.0017(10) C17 0.0408(11) 0.0498(12) 0.0414(11) 0.0014(9) -0.0047(9) 0.0026(9) C18 0.0497(12) 0.0406(11) 0.0411(11) 0.0012(8) 0.0025(9) 0.0014(9) C15 0.0489(13) 0.0717(15) 0.0370(11) 0.0076(10) -0.0007(9) 0.0042(11) C11 0.0411(11) 0.0465(12) 0.0536(13) -0.0040(9) 0.0045(9) 0.0071(9) C12 0.0457(12) 0.0625(14) 0.0581(14) -0.0034(11) 0.0159(10) 0.0040(10) C2 0.0437(12) 0.0657(15) 0.0609(14) -0.0124(11) 0.0097(10) -0.0105(11) O4 0.0618(11) 0.0460(10) 0.1488(18) -0.0166(10) -0.0105(11) -0.0062(8) C4 0.0882(19) 0.0439(13) 0.0696(16) -0.0019(11) 0.0341(14) -0.0177(13) C3 0.0641(17) 0.0688(17) 0.0866(19) -0.0164(14) 0.0259(14) -0.0306(14) C20 0.0489(15) 0.098(2) 0.107(2) -0.0041(17) -0.0097(14) -0.0256(14) _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 O2 C14 1.342(2) . ? O2 C15 1.435(2) . ? O1 C1 1.383(2) . ? O1 C18 1.438(2) . ? C7 C8 1.330(2) . ? C7 C6 1.463(3) . ? C7 H7 0.9300 . ? C6 C1 1.390(3) . ? C6 C5 1.398(3) . ? O5 C19 1.319(2) . ? O5 C20 1.444(3) . ? C8 C19 1.493(3) . ? C8 C9 1.510(3) . ? C1 C2 1.377(3) . ? C10 C14 1.342(2) . ? C10 C11 1.451(3) . ? C10 C9 1.503(3) . ? C16 C17 1.311(3) . ? C16 C15 1.486(3) . ? C16 H16 0.9300 . ? C14 C13 1.498(3) . ? O3 C11 1.222(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C19 O4 1.192(2) . ? C13 C12 1.525(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C5 C4 1.372(3) . ? C5 H5 0.9300 . ? C17 C18 1.486(3) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C11 C12 1.507(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C4 C3 1.376(4) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O2 C15 117.73(14) . . ? C1 O1 C18 116.31(14) . . ? C8 C7 C6 130.08(17) . . ? C8 C7 H7 115.0 . . ? C6 C7 H7 115.0 . . ? C1 C6 C5 117.26(18) . . ? C1 C6 C7 119.74(17) . . ? C5 C6 C7 122.59(18) . . ? C19 O5 C20 117.22(19) . . ? C7 C8 C19 115.44(17) . . ? C7 C8 C9 126.25(17) . . ? C19 C8 C9 118.21(16) . . ? C2 C1 O1 117.40(18) . . ? C2 C1 C6 121.30(19) . . ? O1 C1 C6 121.13(16) . . ? C14 C10 C11 108.24(17) . . ? C14 C10 C9 126.51(17) . . ? C11 C10 C9 125.24(17) . . ? C17 C16 C15 126.66(19) . . ? C17 C16 H16 116.7 . . ? C15 C16 H16 116.7 . . ? C10 C14 O2 121.65(16) . . ? C10 C14 C13 114.54(17) . . ? O2 C14 C13 123.80(16) . . ? C10 C9 C8 111.24(15) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O4 C19 O5 123.31(19) . . ? O4 C19 C8 125.09(19) . . ? O5 C19 C8 111.54(18) . . ? C14 C13 C12 102.66(16) . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C16 C17 C18 127.03(19) . . ? C16 C17 H17 116.5 . . ? C18 C17 H17 116.5 . . ? O1 C18 C17 112.38(16) . . ? O1 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? O1 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? O2 C15 C16 110.35(16) . . ? O2 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O2 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? O3 C11 C10 126.08(19) . . ? O3 C11 C12 125.19(18) . . ? C10 C11 C12 108.73(17) . . ? C11 C12 C13 105.82(16) . . ? C11 C12 H12A 110.6 . . ? C13 C12 H12A 110.6 . . ? C11 C12 H12B 110.6 . . ? C13 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C2 C3 C4 120.1(2) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.184 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 914819' ####################################################################### # # 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_global data_6k #TrackingRef 'cif s- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4E,16E)-11,11-Dimethyl-2,8-dioxa-16-methoxycarbonyltricyclo[16.4.0.09,14]docosane-1(18),4,9(14),16,19,-21-hexaen-13-one ; _chemical_name_common macrocycle _chemical_melting_point 393(2) _chemical_formula_moiety 'C24 H28 O5' _chemical_formula_sum 'C24 H28 O5' _chemical_formula_weight 396.48 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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4362(9) _cell_length_b 10.6638(12) _cell_length_c 12.5335(14) _cell_angle_alpha 76.146(2) _cell_angle_beta 79.366(2) _cell_angle_gamma 84.811(2) _cell_volume 1074.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3828 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.70 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9390 _exptl_absorpt_correction_T_max 0.9488 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10374 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3794 _reflns_number_gt 3285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0772P)^2^+1.1507P] 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 3794 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.2211 _refine_ls_wR_factor_gt 0.2150 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4354(3) 0.5335(2) 0.7359(2) 0.0560(7) Uani 1 1 d . . . O2 O 0.7171(3) 0.7006(3) 0.9619(2) 0.0581(7) Uani 1 1 d . . . O3 O 0.9406(3) 0.2919(2) 0.8898(2) 0.0644(8) Uani 1 1 d . . . C1 C 0.6199(4) 0.4099(3) 0.6410(2) 0.0407(7) Uani 1 1 d . . . C2 C 0.8129(3) 0.4516(3) 0.7652(3) 0.0381(7) Uani 1 1 d . . . C3 C 0.9117(4) 0.7390(3) 0.6724(3) 0.0511(9) Uani 1 1 d . . . H3 H 0.9564 0.6883 0.6225 0.061 Uiso 1 1 calc R . . O4 O 0.7813(4) 0.2247(2) 0.7975(3) 0.0789(10) Uani 1 1 d . . . C4 C 0.8394(4) 0.3125(3) 0.8170(3) 0.0430(7) Uani 1 1 d . . . C5 C 0.8425(4) 0.5388(3) 0.8192(3) 0.0398(7) Uani 1 1 d . . . H5 H 0.8672 0.5061 0.8902 0.048 Uiso 1 1 calc R . . C6 C 0.8405(4) 0.6794(3) 0.7797(3) 0.0405(7) Uani 1 1 d . . . C7 C 0.4645(4) 0.4354(3) 0.6829(3) 0.0432(8) Uani 1 1 d . . . C8 C 0.6573(5) 0.3151(4) 0.5721(3) 0.0535(9) Uani 1 1 d . . . C9 C 0.7790(4) 0.7596(3) 0.8531(3) 0.0474(8) Uani 1 1 d . . . C10 C 0.7560(4) 0.4849(3) 0.6537(3) 0.0430(7) Uani 1 1 d . . . H10A H 0.7225 0.5760 0.6380 0.052 Uiso 1 1 calc R . . H10B H 0.8478 0.4733 0.5970 0.052 Uiso 1 1 calc R . . O5 O 0.7926(4) 0.2958(3) 0.5258(3) 0.0915(11) Uani 1 1 d . . . C11 C 0.3258(4) 0.3619(4) 0.6736(3) 0.0569(9) Uani 1 1 d . . . H11A H 0.2706 0.4129 0.6150 0.068 Uiso 1 1 calc R . . H11B H 0.2497 0.3503 0.7430 0.068 Uiso 1 1 calc R . . C12 C 0.5193(5) 0.2461(4) 0.5544(3) 0.0648(11) Uani 1 1 d . . . H12A H 0.5595 0.1612 0.5433 0.078 Uiso 1 1 calc R . . H12B H 0.4824 0.2937 0.4865 0.078 Uiso 1 1 calc R . . C13 C 0.3764(5) 0.2296(4) 0.6483(3) 0.0579(10) Uani 1 1 d . . . C14 C 0.7854(5) 0.8920(4) 0.8187(4) 0.0609(10) Uani 1 1 d . . . H14 H 0.7439 0.9439 0.8682 0.073 Uiso 1 1 calc R . . C15 C 0.9175(5) 0.8710(4) 0.6389(4) 0.0657(11) Uani 1 1 d . . . H15 H 0.9653 0.9086 0.5666 0.079 Uiso 1 1 calc R . . C16 C 0.2725(5) 0.5753(5) 0.7757(4) 0.0726(12) Uani 1 1 d . . . H16A H 0.2333 0.5217 0.8485 0.087 Uiso 1 1 calc R . . H16B H 0.2019 0.5679 0.7248 0.087 Uiso 1 1 calc R . . C17 C 0.8533(5) 0.9477(4) 0.7110(4) 0.0692(12) Uani 1 1 d . . . H17 H 0.8556 1.0372 0.6873 0.083 Uiso 1 1 calc R . . C18 C 0.9687(6) 0.1604(4) 0.9463(4) 0.0700(12) Uani 1 1 d . . . H18A H 0.8701 0.1278 0.9921 0.105 Uiso 1 1 calc R . . H18B H 1.0492 0.1562 0.9923 0.105 Uiso 1 1 calc R . . H18C H 1.0056 0.1090 0.8925 0.105 Uiso 1 1 calc R . . C19 C 0.5468(5) 0.7259(5) 0.9966(3) 0.0713(12) Uani 1 1 d . . . H19A H 0.5250 0.8182 0.9898 0.086 Uiso 1 1 calc R . . H19B H 0.5157 0.6830 1.0743 0.086 Uiso 1 1 calc R . . C20 C 0.4238(6) 0.1350(4) 0.7511(4) 0.0735(12) Uani 1 1 d . . . H20A H 0.4581 0.0530 0.7333 0.110 Uiso 1 1 calc R . . H20B H 0.3325 0.1241 0.8104 0.110 Uiso 1 1 calc R . . H20C H 0.5105 0.1684 0.7743 0.110 Uiso 1 1 calc R . . C21 C 0.4474(6) 0.6785(5) 0.9265(4) 0.0847(14) Uani 1 1 d . . . H21 H 0.4426 0.5896 0.9359 0.102 Uiso 1 1 calc R . . C22 C 0.3723(6) 0.7497(5) 0.8578(4) 0.0850(14) Uani 1 1 d . . . H22 H 0.3779 0.8379 0.8516 0.102 Uiso 1 1 calc R . . C23 C 0.2331(6) 0.1778(5) 0.6142(5) 0.0909(16) Uani 1 1 d . . . H23A H 0.1990 0.2392 0.5521 0.136 Uiso 1 1 calc R . . H23B H 0.1453 0.1646 0.6759 0.136 Uiso 1 1 calc R . . H23C H 0.2658 0.0972 0.5933 0.136 Uiso 1 1 calc R . . C24 C 0.2737(6) 0.7138(5) 0.7833(5) 0.0920(16) Uani 1 1 d . . . H24A H 0.3089 0.7642 0.7085 0.110 Uiso 1 1 calc R . . H24B H 0.1627 0.7423 0.8060 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0401(13) 0.0604(15) 0.0741(17) -0.0287(13) -0.0123(11) 0.0052(11) O2 0.0596(16) 0.0660(16) 0.0523(15) -0.0193(12) -0.0136(12) 0.0024(12) O3 0.0794(19) 0.0403(14) 0.0793(18) -0.0025(12) -0.0435(15) -0.0003(12) C1 0.0471(18) 0.0383(17) 0.0358(16) -0.0033(13) -0.0101(13) -0.0048(13) C2 0.0283(15) 0.0371(16) 0.0459(17) -0.0067(13) -0.0028(13) -0.0002(12) C3 0.049(2) 0.046(2) 0.059(2) -0.0101(16) -0.0084(16) -0.0118(15) O4 0.100(2) 0.0389(15) 0.114(2) -0.0156(15) -0.065(2) 0.0031(14) C4 0.0392(17) 0.0382(17) 0.0523(19) -0.0108(14) -0.0084(14) -0.0020(13) C5 0.0367(16) 0.0387(17) 0.0427(17) -0.0057(13) -0.0079(13) -0.0025(13) C6 0.0360(16) 0.0390(17) 0.0477(18) -0.0077(14) -0.0117(14) -0.0043(13) C7 0.0445(19) 0.0415(18) 0.0446(18) -0.0064(14) -0.0150(14) -0.0019(14) C8 0.064(2) 0.056(2) 0.0403(19) -0.0131(16) -0.0002(17) -0.0092(17) C9 0.0437(18) 0.0471(19) 0.057(2) -0.0153(16) -0.0187(16) -0.0030(14) C10 0.0431(18) 0.0393(17) 0.0439(18) -0.0057(14) -0.0046(14) -0.0035(13) O5 0.074(2) 0.108(3) 0.102(2) -0.066(2) 0.0220(18) -0.0183(18) C11 0.049(2) 0.064(2) 0.060(2) -0.0078(18) -0.0181(17) -0.0094(17) C12 0.087(3) 0.059(2) 0.057(2) -0.0210(19) -0.018(2) -0.015(2) C13 0.065(2) 0.053(2) 0.058(2) -0.0065(17) -0.0201(18) -0.0183(18) C14 0.067(2) 0.045(2) 0.082(3) -0.026(2) -0.028(2) 0.0037(18) C15 0.076(3) 0.049(2) 0.068(3) 0.0047(19) -0.017(2) -0.023(2) C16 0.042(2) 0.094(3) 0.089(3) -0.037(3) -0.016(2) 0.011(2) C17 0.080(3) 0.0337(19) 0.097(3) -0.006(2) -0.030(2) -0.0091(18) C18 0.088(3) 0.044(2) 0.077(3) -0.0002(19) -0.035(2) 0.0081(19) C19 0.071(3) 0.092(3) 0.054(2) -0.029(2) -0.007(2) 0.008(2) C20 0.081(3) 0.056(2) 0.079(3) 0.006(2) -0.020(2) -0.019(2) C21 0.089(3) 0.088(3) 0.072(3) -0.022(3) -0.002(3) 0.009(3) C22 0.078(3) 0.082(3) 0.093(4) -0.029(3) -0.005(3) 0.010(3) C23 0.098(4) 0.087(3) 0.101(4) -0.015(3) -0.041(3) -0.041(3) C24 0.063(3) 0.106(4) 0.130(4) -0.069(4) -0.035(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.349(4) . ? O1 C16 1.442(4) . ? O2 C9 1.384(4) . ? O2 C19 1.443(5) . ? O3 C4 1.329(4) . ? O3 C18 1.432(4) . ? C1 C7 1.348(5) . ? C1 C8 1.459(5) . ? C1 C10 1.510(4) . ? C2 C5 1.339(4) . ? C2 C4 1.484(4) . ? C2 C10 1.512(4) . ? C3 C15 1.372(5) . ? C3 C6 1.391(5) . ? C3 H3 0.9300 . ? O4 C4 1.189(4) . ? C5 C6 1.462(4) . ? C5 H5 0.9300 . ? C6 C9 1.403(5) . ? C7 C11 1.503(5) . ? C8 O5 1.205(5) . ? C8 C12 1.508(5) . ? C9 C14 1.377(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C13 1.526(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.511(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C20 1.528(5) . ? C13 C23 1.540(5) . ? C14 C17 1.376(6) . ? C14 H14 0.9300 . ? C15 C17 1.368(6) . ? C15 H15 0.9300 . ? C16 C24 1.503(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C21 1.514(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.233(7) . ? C21 H21 0.9300 . ? C22 C24 1.492(7) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C7 O1 C16 120.9(3) . . ? C9 O2 C19 115.6(3) . . ? C4 O3 C18 116.6(3) . . ? C7 C1 C8 119.2(3) . . ? C7 C1 C10 122.3(3) . . ? C8 C1 C10 118.3(3) . . ? C5 C2 C4 118.1(3) . . ? C5 C2 C10 124.4(3) . . ? C4 C2 C10 117.4(3) . . ? C15 C3 C6 121.3(4) . . ? C15 C3 H3 119.3 . . ? C6 C3 H3 119.3 . . ? O4 C4 O3 120.9(3) . . ? O4 C4 C2 126.1(3) . . ? O3 C4 C2 113.1(3) . . ? C2 C5 C6 127.7(3) . . ? C2 C5 H5 116.2 . . ? C6 C5 H5 116.2 . . ? C3 C6 C9 117.3(3) . . ? C3 C6 C5 122.1(3) . . ? C9 C6 C5 120.4(3) . . ? C1 C7 O1 116.6(3) . . ? C1 C7 C11 124.0(3) . . ? O1 C7 C11 119.4(3) . . ? O5 C8 C1 121.7(3) . . ? O5 C8 C12 120.2(3) . . ? C1 C8 C12 118.0(3) . . ? C14 C9 O2 121.5(3) . . ? C14 C9 C6 120.9(3) . . ? O2 C9 C6 117.6(3) . . ? C1 C10 C2 117.4(3) . . ? C1 C10 H10A 108.0 . . ? C2 C10 H10A 108.0 . . ? C1 C10 H10B 108.0 . . ? C2 C10 H10B 108.0 . . ? H10A C10 H10B 107.2 . . ? C7 C11 C13 113.7(3) . . ? C7 C11 H11A 108.8 . . ? C13 C11 H11A 108.8 . . ? C7 C11 H11B 108.8 . . ? C13 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C8 C12 C13 115.2(3) . . ? C8 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C8 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C11 108.0(3) . . ? C12 C13 C20 109.7(4) . . ? C11 C13 C20 110.4(3) . . ? C12 C13 C23 110.8(3) . . ? C11 C13 C23 108.8(4) . . ? C20 C13 C23 109.2(3) . . ? C17 C14 C9 120.1(4) . . ? C17 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C17 C15 C3 120.5(4) . . ? C17 C15 H15 119.8 . . ? C3 C15 H15 119.8 . . ? O1 C16 C24 108.1(4) . . ? O1 C16 H16A 110.1 . . ? C24 C16 H16A 110.1 . . ? O1 C16 H16B 110.1 . . ? C24 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C15 C17 C14 119.8(4) . . ? C15 C17 H17 120.1 . . ? C14 C17 H17 120.1 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 C19 C21 111.1(3) . . ? O2 C19 H19A 109.4 . . ? C21 C19 H19A 109.4 . . ? O2 C19 H19B 109.4 . . ? C21 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C19 124.4(5) . . ? C22 C21 H21 117.8 . . ? C19 C21 H21 117.8 . . ? C21 C22 C24 128.9(5) . . ? C21 C22 H22 115.5 . . ? C24 C22 H22 115.5 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 C16 120.2(4) . . ? C22 C24 H24A 107.3 . . ? C16 C24 H24A 107.3 . . ? C22 C24 H24B 107.3 . . ? C16 C24 H24B 107.3 . . ? H24A C24 H24B 106.9 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.629 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 917199' ####################################################################### # # 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_global data_6n #TrackingRef '6n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (7Z,17E)-2,10-Dioxa-18-methoxycarbonyltricyclo[18.3.0.011,16] tricosane-1(20),7,11(16),12,14,17-hexaen-21-one ; _chemical_name_common ; (7Z,17E)-2,10-Dioxa-18-methoxycarbonyltricyclo(18.3.0.011,16) tricosane-1(20),7,11(16),12,14,17-hexaen-21-one ; _chemical_melting_point 423(2) _chemical_formula_moiety 'C23 H26 O5' _chemical_formula_sum 'C23 H26 O5' _chemical_formula_weight 382.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4423(16) _cell_length_b 12.3999(16) _cell_length_c 13.5967(18) _cell_angle_alpha 90.00 _cell_angle_beta 97.190(2) _cell_angle_gamma 90.00 _cell_volume 2081.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6046 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 22.56 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9700 _exptl_absorpt_correction_T_max 0.9798 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19587 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _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 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3666 _reflns_number_gt 2706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.1018P)^2^+1.0067P] 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 3666 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.2083 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.8060(2) 0.5939(2) 0.24287(18) 0.0589(6) Uani 1 1 d . . . C2 C 0.7774(3) 0.5000(2) 0.2883(2) 0.0729(8) Uani 1 1 d . . . H2 H 0.7065 0.4748 0.2773 0.087 Uiso 1 1 calc R . . C3 C 0.8539(3) 0.4443(3) 0.3494(2) 0.0816(9) Uani 1 1 d . . . H3 H 0.8344 0.3811 0.3796 0.098 Uiso 1 1 calc R . . C4 C 0.9589(3) 0.4801(2) 0.3669(2) 0.0755(8) Uani 1 1 d . . . H4 H 1.0105 0.4409 0.4076 0.091 Uiso 1 1 calc R . . C5 C 0.9873(2) 0.5752(2) 0.32358(18) 0.0603(7) Uani 1 1 d . . . H5 H 1.0579 0.6007 0.3373 0.072 Uiso 1 1 calc R . . C6 C 0.91240(19) 0.63361(19) 0.25977(17) 0.0521(6) Uani 1 1 d . . . C7 C 0.93786(19) 0.73823(19) 0.21768(17) 0.0519(6) Uani 1 1 d . . . H7 H 0.8818 0.7883 0.2113 0.062 Uiso 1 1 calc R . . C8 C 1.03019(18) 0.77142(18) 0.18736(16) 0.0482(5) Uani 1 1 d . . . C9 C 1.12853(19) 0.7025(2) 0.17974(17) 0.0529(6) Uani 1 1 d . . . H9A H 1.1839 0.7209 0.2338 0.063 Uiso 1 1 calc R . . H9B H 1.1092 0.6275 0.1878 0.063 Uiso 1 1 calc R . . C10 C 1.1753(2) 0.7144(2) 0.08373(18) 0.0586(6) Uani 1 1 d . . . C11 C 1.2869(3) 0.7431(3) 0.0782(3) 0.0832(9) Uani 1 1 d . . . C12 C 1.3025(3) 0.7507(4) -0.0303(3) 0.1174(15) Uani 1 1 d . . . H12A H 1.3222 0.8236 -0.0469 0.141 Uiso 1 1 calc R . . H12B H 1.3591 0.7020 -0.0453 0.141 Uiso 1 1 calc R . . C13 C 1.1958(3) 0.7198(4) -0.0875(3) 0.1046(12) Uani 1 1 d . . . H13A H 1.2029 0.6558 -0.1271 0.126 Uiso 1 1 calc R . . H13B H 1.1668 0.7780 -0.1306 0.126 Uiso 1 1 calc R . . C14 C 1.1252(2) 0.6986(2) -0.0076(2) 0.0658(7) Uani 1 1 d . . . C15 C 0.9729(3) 0.6508(3) -0.1251(2) 0.0891(10) Uani 1 1 d . . . H15A H 0.9670 0.7189 -0.1606 0.107 Uiso 1 1 calc R . . H15B H 1.0163 0.6019 -0.1594 0.107 Uiso 1 1 calc R . . C16 C 0.8667(4) 0.6057(5) -0.1205(3) 0.1287(17) Uani 1 1 d . B . H16A H 0.8329 0.5969 -0.1883 0.154 Uiso 1 1 calc R . . H16B H 0.8773 0.5338 -0.0928 0.154 Uiso 1 1 calc R . . C17 C 0.7917(3) 0.6567(5) -0.0691(3) 0.1360(19) Uani 1 1 d . . . H17A H 0.7777 0.7268 -0.0996 0.163 Uiso 1 1 calc R A 1 H17B H 0.8271 0.6696 -0.0025 0.163 Uiso 1 1 calc R A 1 C18 C 0.6838(4) 0.6073(4) -0.0591(3) 0.1161(15) Uani 1 1 d . B 1 H18A H 0.6546 0.5802 -0.1239 0.139 Uiso 1 1 calc R B 1 H18B H 0.6967 0.5452 -0.0159 0.139 Uiso 1 1 calc R B 1 C19A C 0.6057(5) 0.6665(5) -0.0251(5) 0.0795(14) Uani 0.60 1 d PD B 1 C19B C 0.6210(8) 0.5441(10) 0.0017(8) 0.107(3) Uani 0.40 1 d P C 2 C20A C 0.5796(4) 0.6689(5) 0.0654(5) 0.0832(16) Uani 0.60 1 d P B 1 C20B C 0.6020(7) 0.5407(8) 0.0931(8) 0.097(3) Uani 0.40 1 d P C 2 C21 C 0.6276(3) 0.6132(4) 0.1540(3) 0.1012(12) Uani 1 1 d . B 1 H21A H 0.5845 0.6254 0.2076 0.121 Uiso 1 1 calc R B 1 H21B H 0.6299 0.5363 0.1415 0.121 Uiso 1 1 calc R B 1 C22 C 1.0352(2) 0.8870(2) 0.1582(2) 0.0605(6) Uani 1 1 d . . . C23 C 1.1508(3) 1.0315(3) 0.1307(4) 0.1099(13) Uani 1 1 d . . . H23A H 1.1092 1.0450 0.0676 0.165 Uiso 1 1 calc R . . H23B H 1.2261 1.0443 0.1260 0.165 Uiso 1 1 calc R . . H23C H 1.1269 1.0786 0.1795 0.165 Uiso 1 1 calc R . . O1 O 0.73534(14) 0.65395(17) 0.18058(16) 0.0764(6) Uani 1 1 d . . . O2 O 1.02277(17) 0.66729(18) -0.02409(13) 0.0775(6) Uani 1 1 d . . . O3 O 1.35666(19) 0.7592(3) 0.1474(2) 0.1137(10) Uani 1 1 d . . . O4 O 0.95852(19) 0.94493(19) 0.1378(2) 0.1071(9) Uani 1 1 d . . . O5 O 1.13612(15) 0.92084(15) 0.15913(16) 0.0772(6) Uani 1 1 d . . . H19A H 0.566(4) 0.709(4) -0.069(3) 0.168(19) Uiso 1 1 d D . . H20A H 0.533(4) 0.717(4) 0.091(4) 0.154(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0609(15) 0.0604(15) 0.0565(14) -0.0018(12) 0.0121(11) -0.0069(12) C2 0.0804(19) 0.0693(18) 0.0716(17) 0.0012(14) 0.0201(15) -0.0184(15) C3 0.107(3) 0.0656(18) 0.076(2) 0.0100(15) 0.0281(18) -0.0093(17) C4 0.096(2) 0.0733(18) 0.0583(15) 0.0129(13) 0.0151(14) 0.0146(16) C5 0.0639(15) 0.0672(16) 0.0516(14) 0.0016(12) 0.0136(11) 0.0049(12) C6 0.0552(13) 0.0540(13) 0.0486(12) -0.0029(10) 0.0128(10) -0.0014(11) C7 0.0494(13) 0.0534(13) 0.0530(13) -0.0009(10) 0.0062(10) 0.0017(10) C8 0.0512(13) 0.0500(12) 0.0429(11) -0.0052(9) 0.0041(9) -0.0023(10) C9 0.0552(13) 0.0558(14) 0.0486(13) -0.0036(10) 0.0106(10) 0.0001(11) C10 0.0662(15) 0.0577(15) 0.0547(14) -0.0068(11) 0.0191(12) -0.0046(12) C11 0.082(2) 0.097(2) 0.077(2) -0.0168(17) 0.0337(17) -0.0218(17) C12 0.111(3) 0.162(4) 0.087(2) -0.019(2) 0.048(2) -0.046(3) C13 0.131(3) 0.128(3) 0.0634(19) -0.0093(19) 0.043(2) -0.027(3) C14 0.0790(18) 0.0643(16) 0.0566(15) -0.0072(12) 0.0184(13) -0.0068(14) C15 0.104(3) 0.108(3) 0.0522(16) -0.0148(16) -0.0011(16) 0.000(2) C16 0.131(4) 0.186(5) 0.064(2) -0.022(3) -0.007(2) -0.026(3) C17 0.093(3) 0.225(6) 0.083(3) -0.007(3) -0.017(2) -0.023(3) C18 0.107(3) 0.148(4) 0.086(2) 0.020(3) -0.014(2) -0.043(3) C19A 0.066(3) 0.083(4) 0.084(4) 0.009(3) -0.015(3) 0.007(3) C20B 0.086(6) 0.107(7) 0.093(6) -0.007(5) -0.006(5) -0.028(5) C20A 0.051(3) 0.082(4) 0.114(5) -0.007(3) -0.003(3) 0.002(2) C19B 0.079(6) 0.136(9) 0.101(7) -0.006(6) -0.009(5) -0.027(6) C21 0.067(2) 0.125(3) 0.107(3) 0.014(2) -0.0062(18) -0.034(2) C22 0.0615(15) 0.0539(15) 0.0680(16) 0.0001(12) 0.0159(12) 0.0015(12) C23 0.108(3) 0.062(2) 0.160(4) 0.016(2) 0.019(3) -0.0266(19) O1 0.0541(10) 0.0840(13) 0.0881(14) 0.0153(11) -0.0029(9) -0.0156(9) O2 0.0858(14) 0.0998(16) 0.0460(10) -0.0101(9) 0.0044(9) -0.0080(11) O3 0.0727(14) 0.175(3) 0.0973(18) -0.0320(17) 0.0275(13) -0.0394(16) O4 0.0795(14) 0.0722(14) 0.177(3) 0.0431(15) 0.0435(15) 0.0182(12) O5 0.0672(12) 0.0577(11) 0.1054(16) 0.0033(10) 0.0060(10) -0.0160(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 O1 1.363(3) . ? C1 C2 1.385(4) . ? C1 C6 1.404(3) . ? C2 C3 1.370(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 H5 0.9300 . ? C6 C7 1.468(3) . ? C7 C8 1.333(3) . ? C7 H7 0.9300 . ? C8 C22 1.490(3) . ? C8 C9 1.507(3) . ? C9 C10 1.501(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.333(4) . ? C10 C11 1.445(4) . ? C11 O3 1.214(4) . ? C11 C12 1.515(5) . ? C12 C13 1.501(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.502(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O2 1.325(3) . ? C15 C16 1.444(5) . ? C15 O2 1.449(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.386(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.498(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19A 1.345(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19A C20A 1.312(9) . ? C19A H19A 0.899(19) . ? C20B C19B 1.296(14) . ? C20A C21 1.450(7) . ? C20A H20A 0.93(5) . ? C21 O1 1.436(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 O4 1.199(3) . ? C22 O5 1.323(3) . ? C23 O5 1.443(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 123.7(2) . . ? O1 C1 C6 115.6(2) . . ? C2 C1 C6 120.7(3) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 117.6(2) . . ? C5 C6 C7 122.8(2) . . ? C1 C6 C7 119.4(2) . . ? C8 C7 C6 129.0(2) . . ? C8 C7 H7 115.5 . . ? C6 C7 H7 115.5 . . ? C7 C8 C22 116.4(2) . . ? C7 C8 C9 125.8(2) . . ? C22 C8 C9 117.8(2) . . ? C10 C9 C8 114.2(2) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C14 C10 C11 109.1(2) . . ? C14 C10 C9 127.5(2) . . ? C11 C10 C9 123.3(2) . . ? O3 C11 C10 126.8(3) . . ? O3 C11 C12 125.3(3) . . ? C10 C11 C12 107.9(3) . . ? C13 C12 C11 106.0(3) . . ? C13 C12 H12A 110.5 . . ? C11 C12 H12A 110.5 . . ? C13 C12 H12B 110.5 . . ? C11 C12 H12B 110.5 . . ? H12A C12 H12B 108.7 . . ? C12 C13 C14 103.3(3) . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13B 111.1 . . ? C14 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? O2 C14 C10 121.9(2) . . ? O2 C14 C13 124.5(3) . . ? C10 C14 C13 113.6(3) . . ? C16 C15 O2 107.4(3) . . ? C16 C15 H15A 110.2 . . ? O2 C15 H15A 110.2 . . ? C16 C15 H15B 110.2 . . ? O2 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C17 C16 C15 121.5(4) . . ? C17 C16 H16A 107.0 . . ? C15 C16 H16A 107.0 . . ? C17 C16 H16B 107.0 . . ? C15 C16 H16B 107.0 . . ? H16A C16 H16B 106.7 . . ? C16 C17 C18 121.8(5) . . ? C16 C17 H17A 106.9 . . ? C18 C17 H17A 106.9 . . ? C16 C17 H17B 106.9 . . ? C18 C17 H17B 106.9 . . ? H17A C17 H17B 106.7 . . ? C19A C18 C17 120.1(5) . . ? C19A C18 H18A 107.3 . . ? C17 C18 H18A 107.3 . . ? C19A C18 H18B 107.3 . . ? C17 C18 H18B 107.3 . . ? H18A C18 H18B 106.9 . . ? C20A C19A C18 127.5(5) . . ? C20A C19A H19A 115(4) . . ? C18 C19A H19A 117(4) . . ? C19A C20A C21 130.1(5) . . ? C19A C20A H20A 127(3) . . ? C21 C20A H20A 102(3) . . ? O1 C21 C20A 108.4(3) . . ? O1 C21 H21A 110.0 . . ? C20A C21 H21A 110.0 . . ? O1 C21 H21B 110.0 . . ? C20A C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? O4 C22 O5 122.6(2) . . ? O4 C22 C8 125.5(2) . . ? O5 C22 C8 112.0(2) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 O1 C21 118.3(2) . . ? C14 O2 C15 119.4(2) . . ? C22 O5 C23 116.8(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.601 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 917200' ####################################################################### # # 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_global #=== END data_6o #TrackingRef 'scif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (11E,21E)-2,14-Dioxa-22-methoxycarbonyltricyclo[22.3.0.015,20]heptacosane-1(24),11,15(20),16,18,21-hexaen-25-one ; _chemical_name_common macrocycle _chemical_melting_point 375(2) _chemical_formula_moiety 'C27 H34 O5' _chemical_formula_sum 'C27 H34 O5' _chemical_formula_weight 438.54 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.518(2) _cell_length_b 8.3814(13) _cell_length_c 23.699(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.330(3) _cell_angle_gamma 90.00 _cell_volume 2419.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3524 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 20.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9838 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22377 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.08 _reflns_number_total 4261 _reflns_number_gt 3171 _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^)+(0.1045P)^2^+1.1435P] 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 4261 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2250 _refine_ls_wR_factor_gt 0.2082 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 O2 O 0.90184(19) 0.0397(2) 0.06819(10) 0.0618(6) Uani 1 1 d . . . O1 O 0.87965(19) 0.6099(3) 0.20571(10) 0.0657(7) Uani 1 1 d . . . C6 C 1.0166(2) 0.5338(3) 0.15942(12) 0.0458(7) Uani 1 1 d . . . C8 C 0.9221(2) 0.4015(3) 0.06327(12) 0.0437(7) Uani 1 1 d . . . C1 C 0.9882(3) 0.6102(4) 0.20639(13) 0.0512(8) Uani 1 1 d . . . C7 C 0.9258(2) 0.4795(3) 0.11257(12) 0.0449(7) Uani 1 1 d . . . H7 H 0.8569 0.5047 0.1185 0.054 Uiso 1 1 calc R . . C5 C 1.1273(2) 0.5269(4) 0.15929(14) 0.0548(8) Uani 1 1 d . . . H5 H 1.1493 0.4734 0.1295 0.066 Uiso 1 1 calc R . . C14 C 1.0107(3) 0.0518(3) 0.08211(13) 0.0496(7) Uani 1 1 d . . . C10 C 1.0636(3) 0.1827(3) 0.07176(13) 0.0495(7) Uani 1 1 d . . . O4 O 0.8043(2) 0.3293(3) -0.02604(11) 0.0797(8) Uani 1 1 d . . . C9 C 1.0170(3) 0.3334(4) 0.04239(13) 0.0527(8) Uani 1 1 d . . . H9A H 0.9932 0.3132 0.0011 0.063 Uiso 1 1 calc R . . H9B H 1.0748 0.4129 0.0479 0.063 Uiso 1 1 calc R . . O3 O 1.2521(2) 0.2494(3) 0.08773(14) 0.0930(9) Uani 1 1 d . . . C25 C 0.8396(3) 0.6991(4) 0.24659(15) 0.0682(10) Uani 1 1 d . . . H25A H 0.8561 0.8113 0.2432 0.082 Uiso 1 1 calc R . . H25B H 0.8742 0.6641 0.2855 0.082 Uiso 1 1 calc R . . C12 C 1.1977(3) -0.0113(4) 0.11449(18) 0.0743(11) Uani 1 1 d . . . H12A H 1.2400 -0.0091 0.1543 0.089 Uiso 1 1 calc R . . H12B H 1.2368 -0.0752 0.0916 0.089 Uiso 1 1 calc R . . C2 C 1.0671(3) 0.6799(4) 0.24985(14) 0.0643(9) Uani 1 1 d . . . H2 H 1.0470 0.7303 0.2808 0.077 Uiso 1 1 calc R . . O5 O 0.7310(2) 0.4316(4) 0.04081(11) 0.0914(9) Uani 1 1 d . . . C23 C 0.6599(3) 0.5979(5) 0.19294(17) 0.0722(10) Uani 1 1 d . . . H23 H 0.6950 0.5581 0.1653 0.087 Uiso 1 1 calc R . . C3 C 1.1752(3) 0.6743(4) 0.24688(17) 0.0702(10) Uani 1 1 d . . . H3 H 1.2284 0.7234 0.2755 0.084 Uiso 1 1 calc R . . C17 C 0.6906(3) 0.0102(4) 0.10484(16) 0.0674(9) Uani 1 1 d . . . H17A H 0.7174 0.1181 0.1027 0.081 Uiso 1 1 calc R . . H17B H 0.7221 -0.0298 0.1435 0.081 Uiso 1 1 calc R . . C13 C 1.0844(3) -0.0783(4) 0.11115(16) 0.0674(10) Uani 1 1 d . . . H13A H 1.0728 -0.1756 0.0884 0.081 Uiso 1 1 calc R . . H13B H 1.0730 -0.1001 0.1495 0.081 Uiso 1 1 calc R . . C26 C 0.8155(3) 0.3812(4) 0.02219(16) 0.0627(9) Uani 1 1 d . . . C11 C 1.1795(3) 0.1550(4) 0.09046(16) 0.0622(9) Uani 1 1 d . . . C4 C 1.2049(3) 0.5975(4) 0.20240(17) 0.0667(10) Uani 1 1 d . . . H4 H 1.2786 0.5928 0.2012 0.080 Uiso 1 1 calc R . . C18 C 0.5668(3) 0.0156(5) 0.0960(2) 0.0863(12) Uani 1 1 d . . . H18A H 0.5394 -0.0924 0.0967 0.104 Uiso 1 1 calc R . . H18B H 0.5352 0.0603 0.0581 0.104 Uiso 1 1 calc R . . C24 C 0.7204(3) 0.6757(5) 0.23553(16) 0.0709(10) Uani 1 1 d . . . H24 H 0.6849 0.7216 0.2619 0.085 Uiso 1 1 calc R . . C15 C 0.8519(3) -0.1123(4) 0.07506(18) 0.0691(10) Uani 1 1 d . . . H15A H 0.8781 -0.1506 0.1144 0.083 Uiso 1 1 calc R . . H15B H 0.8714 -0.1901 0.0488 0.083 Uiso 1 1 calc R . . C21 C 0.5152(3) 0.3876(5) 0.18456(19) 0.0826(12) Uani 1 1 d . . . H21A H 0.5527 0.3454 0.2220 0.099 Uiso 1 1 calc R . . H21B H 0.4369 0.3750 0.1812 0.099 Uiso 1 1 calc R . . C20 C 0.5472(3) 0.2898(5) 0.13813(17) 0.0739(11) Uani 1 1 d . . . H20A H 0.6244 0.3083 0.1398 0.089 Uiso 1 1 calc R . . H20B H 0.5059 0.3275 0.1007 0.089 Uiso 1 1 calc R . . C16 C 0.7304(3) -0.0910(4) 0.06194(17) 0.0733(10) Uani 1 1 d . . . H16A H 0.6962 -0.1952 0.0605 0.088 Uiso 1 1 calc R . . H16B H 0.7068 -0.0432 0.0238 0.088 Uiso 1 1 calc R . . C19 C 0.5292(3) 0.1135(5) 0.1417(2) 0.0864(13) Uani 1 1 d . . . H19A H 0.4515 0.0944 0.1381 0.104 Uiso 1 1 calc R . . H19B H 0.5677 0.0764 0.1797 0.104 Uiso 1 1 calc R . . C22 C 0.5406(3) 0.5648(5) 0.18311(19) 0.0817(12) Uani 1 1 d . . . H22A H 0.5035 0.6080 0.1457 0.098 Uiso 1 1 calc R . . H22B H 0.5119 0.6190 0.2127 0.098 Uiso 1 1 calc R . . C27 C 0.6339(4) 0.4274(11) -0.0054(3) 0.186(4) Uani 1 1 d . . . H27A H 0.6539 0.4044 -0.0413 0.278 Uiso 1 1 calc R . . H27B H 0.5978 0.5291 -0.0081 0.278 Uiso 1 1 calc R . . H27C H 0.5853 0.3461 0.0024 0.278 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 O2 0.0712(16) 0.0383(12) 0.0800(16) 0.0087(11) 0.0258(12) 0.0017(10) O1 0.0650(15) 0.0709(15) 0.0650(14) -0.0245(12) 0.0227(11) -0.0078(12) C6 0.0560(18) 0.0300(14) 0.0495(17) 0.0042(12) 0.0082(14) 0.0008(12) C8 0.0575(18) 0.0299(14) 0.0421(16) 0.0080(12) 0.0084(13) 0.0011(12) C1 0.057(2) 0.0426(17) 0.0517(18) -0.0006(14) 0.0084(14) -0.0015(14) C7 0.0512(17) 0.0335(14) 0.0503(17) 0.0045(13) 0.0120(13) 0.0060(12) C5 0.0532(19) 0.0468(18) 0.063(2) 0.0052(15) 0.0099(15) 0.0055(14) C14 0.059(2) 0.0443(17) 0.0498(17) -0.0025(13) 0.0204(14) 0.0062(14) C10 0.064(2) 0.0391(16) 0.0495(17) -0.0026(13) 0.0215(14) 0.0054(14) O4 0.0935(19) 0.0862(19) 0.0524(15) -0.0078(13) 0.0023(13) -0.0130(15) C9 0.068(2) 0.0459(17) 0.0474(17) 0.0029(14) 0.0207(15) -0.0006(15) O3 0.0659(16) 0.0737(18) 0.141(3) -0.0006(17) 0.0269(16) -0.0016(14) C25 0.083(3) 0.068(2) 0.058(2) -0.0145(17) 0.0257(18) 0.0010(19) C12 0.075(2) 0.055(2) 0.090(3) -0.0072(19) 0.013(2) 0.0190(18) C2 0.080(3) 0.059(2) 0.0505(19) -0.0088(16) 0.0075(17) -0.0067(18) O5 0.0623(16) 0.130(3) 0.0710(17) -0.0144(16) -0.0070(13) 0.0127(16) C23 0.072(2) 0.072(2) 0.080(3) -0.001(2) 0.031(2) 0.0072(19) C3 0.065(2) 0.062(2) 0.074(2) -0.0001(19) -0.0057(18) -0.0074(18) C17 0.066(2) 0.058(2) 0.076(2) -0.0059(18) 0.0133(18) -0.0083(17) C13 0.083(3) 0.0422(18) 0.076(2) 0.0030(16) 0.0165(19) 0.0144(17) C26 0.075(2) 0.0478(19) 0.059(2) 0.0105(16) 0.0021(18) -0.0036(17) C11 0.065(2) 0.054(2) 0.071(2) -0.0085(17) 0.0208(17) 0.0077(17) C4 0.0497(19) 0.059(2) 0.085(3) 0.0087(19) 0.0024(18) 0.0006(16) C18 0.063(2) 0.079(3) 0.112(3) -0.017(2) 0.012(2) -0.014(2) C24 0.080(3) 0.071(2) 0.068(2) -0.0156(19) 0.029(2) 0.007(2) C15 0.087(3) 0.0388(18) 0.092(3) -0.0011(17) 0.040(2) -0.0020(17) C21 0.057(2) 0.098(3) 0.100(3) -0.004(2) 0.034(2) -0.001(2) C20 0.053(2) 0.081(3) 0.086(3) 0.007(2) 0.0129(18) 0.0083(18) C16 0.088(3) 0.054(2) 0.081(3) -0.0107(18) 0.025(2) -0.0163(19) C19 0.054(2) 0.090(3) 0.120(4) -0.003(3) 0.028(2) -0.012(2) C22 0.069(2) 0.083(3) 0.098(3) -0.008(2) 0.029(2) 0.011(2) C27 0.087(4) 0.285(11) 0.158(6) 0.016(6) -0.027(4) 0.031(5) _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 O2 C14 1.331(4) . ? O2 C15 1.444(4) . ? O1 C1 1.356(4) . ? O1 C25 1.404(4) . ? C6 C5 1.388(4) . ? C6 C1 1.399(4) . ? C6 C7 1.466(4) . ? C8 C7 1.330(4) . ? C8 C26 1.469(4) . ? C8 C9 1.501(4) . ? C1 C2 1.381(4) . ? C7 H7 0.9300 . ? C5 C4 1.371(5) . ? C5 H5 0.9300 . ? C14 C10 1.333(4) . ? C14 C13 1.490(4) . ? C10 C11 1.435(5) . ? C10 C9 1.495(4) . ? O4 C26 1.200(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O3 C11 1.218(4) . ? C25 C24 1.467(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C12 C11 1.503(5) . ? C12 C13 1.511(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C2 C3 1.372(5) . ? C2 H2 0.9300 . ? O5 C26 1.306(4) . ? O5 C27 1.437(6) . ? C23 C24 1.290(5) . ? C23 C22 1.484(5) . ? C23 H23 0.9300 . ? C3 C4 1.358(5) . ? C3 H3 0.9300 . ? C17 C16 1.495(5) . ? C17 C18 1.516(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C4 H4 0.9300 . ? C18 C19 1.516(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C24 H24 0.9300 . ? C15 C16 1.492(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C21 C20 1.499(5) . ? C21 C22 1.521(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C20 C19 1.500(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O2 C15 119.0(2) . . ? C1 O1 C25 120.5(2) . . ? C5 C6 C1 117.2(3) . . ? C5 C6 C7 125.8(3) . . ? C1 C6 C7 116.7(3) . . ? C7 C8 C26 118.8(3) . . ? C7 C8 C9 127.3(3) . . ? C26 C8 C9 113.8(3) . . ? O1 C1 C2 123.5(3) . . ? O1 C1 C6 115.3(3) . . ? C2 C1 C6 121.2(3) . . ? C8 C7 C6 133.0(3) . . ? C8 C7 H7 113.5 . . ? C6 C7 H7 113.5 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? O2 C14 C10 122.8(3) . . ? O2 C14 C13 123.2(3) . . ? C10 C14 C13 114.0(3) . . ? C14 C10 C11 108.6(3) . . ? C14 C10 C9 128.6(3) . . ? C11 C10 C9 122.7(3) . . ? C10 C9 C8 115.0(2) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O1 C25 C24 108.4(3) . . ? O1 C25 H25A 110.0 . . ? C24 C25 H25A 110.0 . . ? O1 C25 H25B 110.0 . . ? C24 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C11 C12 C13 105.5(3) . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C26 O5 C27 110.1(4) . . ? C24 C23 C22 127.2(4) . . ? C24 C23 H23 116.4 . . ? C22 C23 H23 116.4 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C16 C17 C18 114.4(3) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C14 C13 C12 103.0(3) . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? O4 C26 O5 120.9(3) . . ? O4 C26 C8 124.2(4) . . ? O5 C26 C8 114.9(3) . . ? O3 C11 C10 126.3(3) . . ? O3 C11 C12 125.0(3) . . ? C10 C11 C12 108.8(3) . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C17 C18 C19 113.2(3) . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.8 . . ? C23 C24 C25 126.6(3) . . ? C23 C24 H24 116.7 . . ? C25 C24 H24 116.7 . . ? O2 C15 C16 108.6(3) . . ? O2 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O2 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C20 C21 C22 115.1(3) . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C20 C19 115.4(3) . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20B 108.4 . . ? C19 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C15 C16 C17 114.2(3) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C20 C19 C18 114.7(4) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C23 C22 C21 112.8(3) . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.947 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 915411' ####################################################################### # # 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_global #===END data_7a-E #TrackingRef 'scif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4E,15E)-10,10-Dimethyl-2,7-dioxa-15-methoxycarbonyltricyclo[15.3.1.08,13]henicosane-1(21),4,-8(13),15,17,19-hexaen-12-one ; _chemical_name_common macrocycle _chemical_melting_point 443(2) _chemical_formula_moiety 'C23 H26 O5' _chemical_formula_sum 'C23 H26 O5' _chemical_formula_weight 382.44 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.1101(10) _cell_length_b 12.3001(10) _cell_length_c 13.4920(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2009.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3450 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 19658 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _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 2.24 _diffrn_reflns_theta_max 25.13 _reflns_number_total 3606 _reflns_number_gt 3308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction ? _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^)+(0.0542P)^2^+0.7367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(17) _refine_ls_number_reflns 3606 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 O2 O 0.22860(18) 0.91690(18) 0.72012(17) 0.0536(6) Uani 1 1 d . . . O5 O -0.27579(18) 0.7701(2) 0.65543(18) 0.0633(7) Uani 1 1 d . . . C10 C 0.1202(2) 0.7636(2) 0.6983(2) 0.0385(7) Uani 1 1 d . . . O1 O 0.1203(2) 0.8743(2) 1.06907(17) 0.0623(7) Uani 1 1 d . . . O4 O -0.1519(2) 0.8195(2) 0.54316(19) 0.0723(8) Uani 1 1 d . . . C15 C 0.2193(2) 0.8060(2) 0.7200(2) 0.0408(7) Uani 1 1 d . . . C11 C 0.1143(3) 0.6477(3) 0.6738(2) 0.0471(8) Uani 1 1 d . . . C6 C -0.0533(2) 0.7312(2) 0.8846(2) 0.0401(7) Uani 1 1 d . . . C2 C 0.0626(3) 0.7964(3) 1.0171(2) 0.0473(8) Uani 1 1 d . . . C3 C 0.0670(3) 0.6929(3) 1.0565(3) 0.0604(10) Uani 1 1 d . . . H3 H 0.1071 0.6796 1.1140 0.072 Uiso 1 1 calc R . . C13 C 0.3022(3) 0.6217(3) 0.7579(3) 0.0503(8) Uani 1 1 d . . . C8 C -0.0915(2) 0.7909(2) 0.7092(2) 0.0385(7) Uani 1 1 d . . . C14 C 0.3230(2) 0.7408(3) 0.7335(3) 0.0529(8) Uani 1 1 d . . . H14A H 0.3662 0.7730 0.7864 0.063 Uiso 1 1 calc R . . H14B H 0.3663 0.7450 0.6731 0.063 Uiso 1 1 calc R . . C20 C -0.1738(3) 0.7959(3) 0.6270(3) 0.0466(8) Uani 1 1 d . . . O3 O 0.0313(2) 0.6077(2) 0.6388(2) 0.0695(8) Uani 1 1 d . . . C5 C -0.0498(3) 0.6288(3) 0.9264(2) 0.0537(9) Uani 1 1 d . . . H5 H -0.0895 0.5723 0.8976 0.064 Uiso 1 1 calc R . . C1 C 0.0030(3) 0.8165(3) 0.9310(2) 0.0423(7) Uani 1 1 d . . . H1 H 0.0006 0.8862 0.9044 0.051 Uiso 1 1 calc R . . C7 C -0.1212(2) 0.7483(2) 0.7956(2) 0.0398(7) Uani 1 1 d . . . H7 H -0.1945 0.7264 0.8004 0.048 Uiso 1 1 calc R . . C9 C 0.0211(2) 0.8365(3) 0.6827(2) 0.0453(7) Uani 1 1 d . . . H9A H 0.0195 0.8576 0.6135 0.054 Uiso 1 1 calc R . . H9B H 0.0323 0.9022 0.7212 0.054 Uiso 1 1 calc R . . C12 C 0.2169(3) 0.5792(3) 0.6852(3) 0.0581(9) Uani 1 1 d . . . H12A H 0.2517 0.5723 0.6208 0.070 Uiso 1 1 calc R . . H12B H 0.1949 0.5070 0.7061 0.070 Uiso 1 1 calc R . . C16 C 0.2934(3) 0.9691(3) 0.7970(3) 0.0588(9) Uani 1 1 d . . . H16A H 0.2942 1.0471 0.7862 0.071 Uiso 1 1 calc R . . H16B H 0.3689 0.9431 0.7941 0.071 Uiso 1 1 calc R . . C17 C 0.2447(3) 0.9445(3) 0.8989(4) 0.0743(12) Uani 1 1 d . . . H17 H 0.2635 0.8791 0.9292 0.089 Uiso 1 1 calc R . . C4 C 0.0117(3) 0.6094(3) 1.0101(3) 0.0626(10) Uani 1 1 d . . . H4 H 0.0160 0.5393 1.0357 0.075 Uiso 1 1 calc R . . C19 C 0.1170(3) 0.9823(3) 1.0341(3) 0.0639(10) Uani 1 1 d . . . H19A H 0.1430 1.0295 1.0867 0.077 Uiso 1 1 calc R . . H19B H 0.0404 1.0010 1.0215 0.077 Uiso 1 1 calc R . . C18 C 0.1813(3) 1.0070(4) 0.9436(3) 0.0708(11) Uani 1 1 d . . . H18 H 0.1735 1.0765 0.9175 0.085 Uiso 1 1 calc R . . C23 C 0.2610(3) 0.6114(3) 0.8639(3) 0.0685(11) Uani 1 1 d . . . H23A H 0.1948 0.6535 0.8718 0.103 Uiso 1 1 calc R . . H23B H 0.3166 0.6377 0.9087 0.103 Uiso 1 1 calc R . . H23C H 0.2456 0.5365 0.8782 0.103 Uiso 1 1 calc R . . C22 C 0.4097(3) 0.5575(3) 0.7467(3) 0.0719(12) Uani 1 1 d . . . H22A H 0.3970 0.4829 0.7642 0.108 Uiso 1 1 calc R . . H22B H 0.4649 0.5877 0.7897 0.108 Uiso 1 1 calc R . . H22C H 0.4346 0.5617 0.6793 0.108 Uiso 1 1 calc R . . C21 C -0.3588(3) 0.7692(5) 0.5785(3) 0.0916(15) Uani 1 1 d . . . H21A H -0.3700 0.8418 0.5545 0.137 Uiso 1 1 calc R . . H21B H -0.4269 0.7416 0.6049 0.137 Uiso 1 1 calc R . . H21C H -0.3347 0.7235 0.5250 0.137 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 O2 0.0467(12) 0.0498(13) 0.0644(14) 0.0020(11) -0.0021(11) -0.0102(10) O5 0.0388(12) 0.0882(18) 0.0628(15) 0.0083(13) -0.0179(11) -0.0064(12) C10 0.0353(14) 0.0486(17) 0.0316(15) 0.0006(13) 0.0034(12) -0.0043(13) O1 0.0710(16) 0.0750(17) 0.0407(13) -0.0014(12) -0.0149(12) 0.0019(14) O4 0.0665(17) 0.103(2) 0.0478(15) 0.0147(14) -0.0146(13) -0.0077(15) C15 0.0439(16) 0.0425(17) 0.0361(15) 0.0005(13) 0.0088(13) -0.0052(14) C11 0.0397(17) 0.0560(19) 0.0455(18) -0.0064(15) 0.0010(14) -0.0048(15) C6 0.0342(14) 0.0488(18) 0.0373(16) 0.0040(14) 0.0088(13) -0.0003(13) C2 0.0425(17) 0.068(2) 0.0312(15) 0.0011(15) 0.0016(13) 0.0024(16) C3 0.062(2) 0.080(3) 0.0390(18) 0.0203(19) -0.0007(16) 0.008(2) C13 0.0376(17) 0.057(2) 0.056(2) -0.0084(16) -0.0018(15) 0.0049(15) C8 0.0357(15) 0.0359(15) 0.0439(17) -0.0014(13) -0.0027(13) 0.0030(12) C14 0.0321(15) 0.068(2) 0.058(2) -0.0084(17) 0.0048(14) -0.0016(15) C20 0.0447(18) 0.0469(18) 0.048(2) -0.0045(16) -0.0085(14) 0.0028(15) O3 0.0448(13) 0.0672(17) 0.096(2) -0.0277(15) -0.0142(13) -0.0079(12) C5 0.057(2) 0.056(2) 0.049(2) 0.0092(16) 0.0025(16) -0.0105(17) C1 0.0428(17) 0.0440(17) 0.0403(16) 0.0013(13) 0.0013(14) 0.0008(14) C7 0.0306(14) 0.0419(16) 0.0468(18) -0.0037(14) 0.0015(13) -0.0004(12) C9 0.0435(17) 0.0506(18) 0.0419(16) 0.0083(14) -0.0077(14) -0.0049(14) C12 0.056(2) 0.0475(18) 0.071(2) -0.0111(17) -0.0011(18) -0.0001(16) C16 0.0474(19) 0.058(2) 0.071(2) -0.0056(18) 0.0050(18) -0.0171(16) C17 0.061(3) 0.063(2) 0.099(3) -0.014(2) -0.018(2) -0.009(2) C4 0.070(2) 0.059(2) 0.059(2) 0.0227(18) 0.005(2) 0.001(2) C19 0.066(2) 0.078(3) 0.048(2) -0.0183(19) -0.0102(18) -0.005(2) C18 0.065(3) 0.068(3) 0.080(3) -0.010(2) -0.005(2) -0.014(2) C23 0.068(2) 0.082(3) 0.056(2) 0.008(2) 0.0084(19) 0.014(2) C22 0.053(2) 0.078(3) 0.085(3) -0.020(2) -0.003(2) 0.0181(19) C21 0.060(2) 0.128(4) 0.087(3) 0.009(3) -0.036(2) -0.007(3) _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 O2 C15 1.369(4) . ? O2 C16 1.451(4) . ? O5 C20 1.331(4) . ? O5 C21 1.445(4) . ? C10 C15 1.341(4) . ? C10 C11 1.464(4) . ? C10 C9 1.513(4) . ? O1 C2 1.377(4) . ? O1 C19 1.410(5) . ? O4 C20 1.198(4) . ? C15 C14 1.501(4) . ? C11 O3 1.215(4) . ? C11 C12 1.510(5) . ? C6 C5 1.381(5) . ? C6 C1 1.400(4) . ? C6 C7 1.471(4) . ? C2 C3 1.381(5) . ? C2 C1 1.390(4) . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C13 C12 1.517(5) . ? C13 C23 1.520(5) . ? C13 C14 1.522(5) . ? C13 C22 1.530(4) . ? C8 C7 1.328(4) . ? C8 C20 1.492(4) . ? C8 C9 1.517(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C5 C4 1.374(5) . ? C5 H5 0.9300 . ? C1 H1 0.9300 . ? C7 H7 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C16 C17 1.526(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.242(6) . ? C17 H17 0.9300 . ? C4 H4 0.9300 . ? C19 C18 1.480(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C18 H18 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 C16 119.1(3) . . ? C20 O5 C21 116.1(3) . . ? C15 C10 C11 118.1(3) . . ? C15 C10 C9 120.6(3) . . ? C11 C10 C9 120.4(3) . . ? C2 O1 C19 118.1(3) . . ? C10 C15 O2 117.5(3) . . ? C10 C15 C14 124.6(3) . . ? O2 C15 C14 117.6(3) . . ? O3 C11 C10 121.5(3) . . ? O3 C11 C12 119.6(3) . . ? C10 C11 C12 118.7(3) . . ? C5 C6 C1 119.1(3) . . ? C5 C6 C7 118.8(3) . . ? C1 C6 C7 122.0(3) . . ? O1 C2 C3 115.2(3) . . ? O1 C2 C1 124.4(3) . . ? C3 C2 C1 120.4(3) . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C12 C13 C23 110.9(3) . . ? C12 C13 C14 107.7(3) . . ? C23 C13 C14 109.8(3) . . ? C12 C13 C22 109.7(3) . . ? C23 C13 C22 109.2(3) . . ? C14 C13 C22 109.5(3) . . ? C7 C8 C20 119.2(3) . . ? C7 C8 C9 126.6(3) . . ? C20 C8 C9 114.3(3) . . ? C15 C14 C13 113.7(2) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? O4 C20 O5 122.4(3) . . ? O4 C20 C8 124.3(3) . . ? O5 C20 C8 113.4(3) . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C2 C1 C6 119.6(3) . . ? C2 C1 H1 120.2 . . ? C6 C1 H1 120.2 . . ? C8 C7 C6 128.5(3) . . ? C8 C7 H7 115.7 . . ? C6 C7 H7 115.7 . . ? C10 C9 C8 117.5(2) . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9B 107.9 . . ? C8 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? C11 C12 C13 115.7(3) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.4 . . ? O2 C16 C17 110.3(3) . . ? O2 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? O2 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 123.6(4) . . ? C18 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? O1 C19 C18 117.0(3) . . ? O1 C19 H19A 108.0 . . ? C18 C19 H19A 108.0 . . ? O1 C19 H19B 108.0 . . ? C18 C19 H19B 108.0 . . ? H19A C19 H19B 107.3 . . ? C17 C18 C19 126.8(4) . . ? C17 C18 H18 116.6 . . ? C19 C18 H18 116.6 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C13 C22 H22A 109.5 . . ? C13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.573 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 915412' ####################################################################### # # 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_global data_7a-Z #TrackingRef '7a-Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4Z,15E)-10,10-Dimethyl-2,7-dioxa-15-methoxycarbonyltricyclo [15.3.1.08,13]henicosane-1(21),4,8(13),15,17,19-hexaen-12-one ; _chemical_name_common ; (4Z,15E)-10,10-Dimethyl-2,7-dioxa-15-methoxycarbonyltricyclo (15.3.1.08,13)henicosane-1(21),4,8(13),15,17,19-hexaen-12-one ; _chemical_melting_point 435(2) _chemical_formula_moiety 'C23 H26 O5' _chemical_formula_sum 'C23 H26 O5' _chemical_formula_weight 382.44 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 ' 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 25.1535(18) _cell_length_b 8.7953(6) _cell_length_c 36.307(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.4190(10) _cell_angle_gamma 90.00 _cell_volume 7982.0(10) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8527 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.07 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3264 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9738 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 37247 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7035 _reflns_number_gt 6253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0586P)^2^+18.7062P] 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 7035 _refine_ls_number_parameters 511 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1482 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.36356(6) 0.16539(18) 0.14005(4) 0.0240(3) Uani 1 1 d . . . O6 O 0.52093(6) 0.40902(18) 0.11539(5) 0.0313(4) Uani 1 1 d . . . O5 O 0.21348(7) -0.13318(19) 0.10429(5) 0.0331(4) Uani 1 1 d . . . O4 O 0.20789(6) 0.45205(18) 0.13118(5) 0.0298(4) Uani 1 1 d . . . O3 O 0.18613(7) 0.22241(19) 0.10761(5) 0.0325(4) Uani 1 1 d . . . O9 O 0.35392(7) 0.6094(2) 0.13921(5) 0.0364(4) Uani 1 1 d . . . O2 O 0.42040(6) 0.0789(2) 0.25452(4) 0.0318(4) Uani 1 1 d . . . O8 O 0.41884(7) 0.7830(2) 0.14911(5) 0.0371(4) Uani 1 1 d . . . O7 O 0.49024(8) 0.1968(2) -0.00134(5) 0.0468(5) Uani 1 1 d . . . O10 O 0.52298(8) 0.9377(2) 0.12420(6) 0.0495(5) Uani 1 1 d . . . C38 C 0.54064(8) 0.5400(3) 0.13170(6) 0.0235(5) Uani 1 1 d . . . C10 C 0.28591(8) 0.0299(2) 0.12222(6) 0.0206(4) Uani 1 1 d . . . C15 C 0.33480(8) 0.0763(2) 0.11458(6) 0.0205(4) Uani 1 1 d . . . C43 C 0.39842(9) 0.6794(3) 0.13110(6) 0.0247(5) Uani 1 1 d . . . C2 C 0.37150(9) 0.1477(3) 0.25614(6) 0.0275(5) Uani 1 1 d . . . C31 C 0.41881(8) 0.6183(3) 0.09693(6) 0.0232(5) Uani 1 1 d . . . C9 C 0.26160(8) 0.0710(2) 0.15716(6) 0.0228(5) Uani 1 1 d . . . H9A H 0.2870 0.0398 0.1787 0.027 Uiso 1 1 calc R . . H9B H 0.2287 0.0099 0.1579 0.027 Uiso 1 1 calc R . . C20 C 0.21111(8) 0.3003(3) 0.13091(6) 0.0230(5) Uani 1 1 d . . . C1 C 0.33918(9) 0.1961(3) 0.22495(6) 0.0254(5) Uani 1 1 d . . . H1 H 0.3507 0.1817 0.2011 0.031 Uiso 1 1 calc R . . C8 C 0.24739(8) 0.2367(2) 0.16228(6) 0.0212(5) Uani 1 1 d . . . C4 C 0.30651(10) 0.2385(3) 0.29424(6) 0.0321(5) Uani 1 1 d . . . H4 H 0.2952 0.2528 0.3181 0.038 Uiso 1 1 calc R . . C14 C 0.35859(9) 0.0377(3) 0.07971(6) 0.0241(5) Uani 1 1 d . . . H14A H 0.3852 -0.0445 0.0851 0.029 Uiso 1 1 calc R . . H14B H 0.3777 0.1279 0.0716 0.029 Uiso 1 1 calc R . . C3 C 0.35461(10) 0.1672(3) 0.29104(6) 0.0295(5) Uani 1 1 d . . . H3 H 0.3761 0.1316 0.3125 0.035 Uiso 1 1 calc R . . C29 C 0.39682(9) 0.4571(3) 0.03905(6) 0.0282(5) Uani 1 1 d . . . C7 C 0.25700(8) 0.3155(3) 0.19403(6) 0.0237(5) Uani 1 1 d . . . H7 H 0.2409 0.4130 0.1947 0.028 Uiso 1 1 calc R . . C5 C 0.27427(10) 0.2897(3) 0.26316(6) 0.0292(5) Uani 1 1 d . . . H5 H 0.2417 0.3409 0.2658 0.035 Uiso 1 1 calc R . . C17 C 0.44304(9) 0.2784(3) 0.17057(7) 0.0303(5) Uani 1 1 d . . . H17 H 0.4520 0.3813 0.1663 0.036 Uiso 1 1 calc R . . C32 C 0.47252(9) 0.6797(3) 0.08874(6) 0.0257(5) Uani 1 1 d . . . H32A H 0.4839 0.6228 0.0674 0.031 Uiso 1 1 calc R . . H32B H 0.4678 0.7874 0.0811 0.031 Uiso 1 1 calc R . . C6 C 0.29008(9) 0.2656(3) 0.22795(6) 0.0253(5) Uani 1 1 d . . . C36 C 0.58310(9) 0.6551(3) 0.19123(7) 0.0303(5) Uani 1 1 d . . . C35 C 0.57997(10) 0.8053(3) 0.17019(7) 0.0335(6) Uani 1 1 d . . . H35A H 0.5733 0.8877 0.1877 0.040 Uiso 1 1 calc R . . H35B H 0.6152 0.8252 0.1614 0.040 Uiso 1 1 calc R . . C33 C 0.51674(8) 0.6711(3) 0.12033(6) 0.0244(5) Uani 1 1 d . . . C16 C 0.42064(8) 0.1861(3) 0.13774(6) 0.0271(5) Uani 1 1 d . . . H16A H 0.4263 0.2395 0.1145 0.032 Uiso 1 1 calc R . . H16B H 0.4388 0.0861 0.1379 0.032 Uiso 1 1 calc R . . C24 C 0.44212(9) 0.3687(3) 0.03624(7) 0.0314(5) Uani 1 1 d . . . H24 H 0.4688 0.3600 0.0568 0.038 Uiso 1 1 calc R . . C18 C 0.45141(9) 0.2281(3) 0.20505(7) 0.0300(5) Uani 1 1 d . . . H18 H 0.4665 0.2983 0.2232 0.036 Uiso 1 1 calc R . . C11 C 0.25604(9) -0.0786(2) 0.09721(6) 0.0234(5) Uani 1 1 d . . . C37 C 0.58474(9) 0.5258(3) 0.16309(6) 0.0278(5) Uani 1 1 d . . . H37A H 0.6197 0.5270 0.1530 0.033 Uiso 1 1 calc R . . H37B H 0.5813 0.4272 0.1758 0.033 Uiso 1 1 calc R . . C28 C 0.35803(10) 0.4696(3) 0.00857(7) 0.0355(6) Uani 1 1 d . . . H28 H 0.3266 0.5275 0.0104 0.043 Uiso 1 1 calc R . . C12 C 0.28047(9) -0.1304(3) 0.06317(6) 0.0277(5) Uani 1 1 d . . . H12A H 0.2513 -0.1559 0.0435 0.033 Uiso 1 1 calc R . . H12B H 0.3012 -0.2244 0.0693 0.033 Uiso 1 1 calc R . . C19 C 0.43963(9) 0.0724(3) 0.21853(6) 0.0301(5) Uani 1 1 d . . . H19A H 0.4123 0.0233 0.2006 0.036 Uiso 1 1 calc R . . H19B H 0.4725 0.0098 0.2201 0.036 Uiso 1 1 calc R . . C30 C 0.38682(9) 0.5282(3) 0.07459(6) 0.0261(5) Uani 1 1 d . . . H30 H 0.3529 0.5069 0.0826 0.031 Uiso 1 1 calc R . . C13 C 0.31705(9) -0.0134(3) 0.04796(6) 0.0259(5) Uani 1 1 d . . . C25 C 0.44841(10) 0.2930(3) 0.00333(7) 0.0353(6) Uani 1 1 d . . . C26 C 0.41024(11) 0.3090(3) -0.02721(7) 0.0397(7) Uani 1 1 d . . . H26 H 0.4149 0.2594 -0.0499 0.048 Uiso 1 1 calc R . . C34 C 0.53742(9) 0.8134(3) 0.13723(7) 0.0317(6) Uani 1 1 d . . . C46 C 0.63325(10) 0.6480(4) 0.21901(7) 0.0413(7) Uani 1 1 d . . . H46A H 0.6651 0.6516 0.2057 0.062 Uiso 1 1 calc R . . H46B H 0.6333 0.5532 0.2332 0.062 Uiso 1 1 calc R . . H46C H 0.6336 0.7348 0.2360 0.062 Uiso 1 1 calc R . . C21 C 0.17118(10) 0.5172(3) 0.10183(7) 0.0364(6) Uani 1 1 d . . . H21A H 0.1799 0.4794 0.0778 0.055 Uiso 1 1 calc R . . H21B H 0.1744 0.6282 0.1025 0.055 Uiso 1 1 calc R . . H21C H 0.1345 0.4880 0.1053 0.055 Uiso 1 1 calc R . . C40 C 0.58216(10) 0.3220(3) 0.07630(8) 0.0389(6) Uani 1 1 d . . . H40 H 0.6113 0.3913 0.0788 0.047 Uiso 1 1 calc R . . C23 C 0.34632(11) -0.0839(3) 0.01745(7) 0.0367(6) Uani 1 1 d . . . H23A H 0.3677 -0.1705 0.0275 0.055 Uiso 1 1 calc R . . H23B H 0.3699 -0.0077 0.0081 0.055 Uiso 1 1 calc R . . H23C H 0.3201 -0.1186 -0.0028 0.055 Uiso 1 1 calc R . . C22 C 0.28457(10) 0.1234(3) 0.03211(7) 0.0327(6) Uani 1 1 d . . . H22A H 0.2588 0.0902 0.0114 0.049 Uiso 1 1 calc R . . H22B H 0.3087 0.1993 0.0233 0.049 Uiso 1 1 calc R . . H22C H 0.2653 0.1683 0.0515 0.049 Uiso 1 1 calc R . . C27 C 0.36542(12) 0.3973(3) -0.02440(7) 0.0423(7) Uani 1 1 d . . . H27 H 0.3394 0.4087 -0.0453 0.051 Uiso 1 1 calc R . . C44 C 0.33196(12) 0.6632(3) 0.17181(7) 0.0419(7) Uani 1 1 d . . . H44A H 0.3568 0.6398 0.1938 0.063 Uiso 1 1 calc R . . H44B H 0.2976 0.6129 0.1738 0.063 Uiso 1 1 calc R . . H44C H 0.3265 0.7734 0.1700 0.063 Uiso 1 1 calc R . . C42 C 0.52609(11) 0.1486(3) 0.03314(8) 0.0422(7) Uani 1 1 d . . . H42A H 0.5045 0.1360 0.0541 0.051 Uiso 1 1 calc R . . H42B H 0.5432 0.0500 0.0287 0.051 Uiso 1 1 calc R . . C45 C 0.53397(10) 0.6396(3) 0.21254(7) 0.0400(6) Uani 1 1 d . . . H45A H 0.5343 0.7212 0.2309 0.060 Uiso 1 1 calc R . . H45B H 0.5349 0.5409 0.2251 0.060 Uiso 1 1 calc R . . H45C H 0.5013 0.6469 0.1952 0.060 Uiso 1 1 calc R . . C39 C 0.55786(11) 0.2869(3) 0.10911(7) 0.0399(6) Uani 1 1 d . . . H39A H 0.5856 0.2777 0.1306 0.048 Uiso 1 1 calc R . . H39B H 0.5384 0.1891 0.1060 0.048 Uiso 1 1 calc R . . C41 C 0.56722(11) 0.2653(3) 0.04219(8) 0.0405(6) Uani 1 1 d . . . H41 H 0.5848 0.3041 0.0223 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0182(7) 0.0295(8) 0.0243(8) -0.0030(7) 0.0027(6) -0.0026(6) O6 0.0322(9) 0.0229(8) 0.0368(9) -0.0082(7) -0.0053(7) 0.0037(7) O5 0.0292(9) 0.0294(9) 0.0407(10) -0.0035(8) 0.0038(7) -0.0080(7) O4 0.0289(8) 0.0242(9) 0.0348(9) 0.0033(7) -0.0036(7) 0.0005(7) O3 0.0342(9) 0.0304(9) 0.0306(9) -0.0056(7) -0.0069(7) 0.0055(7) O9 0.0398(10) 0.0376(10) 0.0354(10) -0.0040(8) 0.0196(8) -0.0092(8) O2 0.0329(9) 0.0386(10) 0.0224(8) 0.0029(7) -0.0024(7) 0.0090(8) O8 0.0289(9) 0.0412(10) 0.0422(10) -0.0136(9) 0.0086(8) -0.0023(8) O7 0.0442(11) 0.0618(13) 0.0352(10) -0.0243(9) 0.0076(8) -0.0022(10) O10 0.0399(11) 0.0227(10) 0.0848(16) -0.0032(10) 0.0022(10) -0.0023(8) C38 0.0206(11) 0.0256(12) 0.0251(11) -0.0061(9) 0.0060(9) -0.0019(9) C10 0.0211(10) 0.0183(10) 0.0223(11) 0.0022(9) 0.0024(8) 0.0026(8) C15 0.0220(11) 0.0183(10) 0.0209(11) 0.0022(8) 0.0005(8) 0.0031(9) C43 0.0223(11) 0.0244(12) 0.0270(12) 0.0043(10) 0.0007(9) 0.0048(9) C2 0.0310(12) 0.0240(12) 0.0270(12) 0.0005(9) 0.0002(10) -0.0003(10) C31 0.0213(11) 0.0237(11) 0.0248(11) 0.0054(9) 0.0033(9) 0.0034(9) C9 0.0204(10) 0.0242(11) 0.0243(11) 0.0035(9) 0.0039(9) -0.0010(9) C20 0.0194(10) 0.0256(12) 0.0253(11) -0.0007(9) 0.0080(9) 0.0018(9) C1 0.0268(11) 0.0296(12) 0.0196(11) 0.0000(9) 0.0016(9) -0.0007(10) C8 0.0153(10) 0.0239(11) 0.0254(11) 0.0011(9) 0.0069(8) -0.0018(8) C4 0.0452(14) 0.0294(13) 0.0224(12) -0.0037(10) 0.0071(10) -0.0034(11) C14 0.0228(11) 0.0259(12) 0.0241(11) 0.0027(9) 0.0051(9) 0.0031(9) C3 0.0424(14) 0.0251(12) 0.0200(11) 0.0006(9) -0.0012(10) -0.0009(10) C29 0.0273(12) 0.0330(13) 0.0245(11) 0.0015(10) 0.0035(9) -0.0077(10) C7 0.0196(10) 0.0244(11) 0.0281(12) 0.0012(9) 0.0067(9) 0.0004(9) C5 0.0311(12) 0.0286(12) 0.0287(12) -0.0054(10) 0.0063(10) -0.0013(10) C17 0.0218(11) 0.0343(13) 0.0344(13) 0.0022(11) 0.0017(10) -0.0039(10) C32 0.0267(12) 0.0224(11) 0.0286(12) 0.0026(9) 0.0068(9) 0.0007(9) C6 0.0272(11) 0.0231(11) 0.0256(11) -0.0025(9) 0.0030(9) -0.0036(9) C36 0.0229(11) 0.0412(14) 0.0283(12) -0.0106(11) 0.0095(9) -0.0099(10) C35 0.0291(12) 0.0338(13) 0.0395(14) -0.0145(11) 0.0128(11) -0.0118(10) C33 0.0195(11) 0.0246(12) 0.0307(12) -0.0028(9) 0.0096(9) -0.0011(9) C16 0.0174(10) 0.0374(13) 0.0265(12) 0.0042(10) 0.0031(9) -0.0011(9) C24 0.0281(12) 0.0418(14) 0.0244(12) -0.0060(11) 0.0036(9) -0.0079(11) C18 0.0193(11) 0.0385(14) 0.0310(13) -0.0040(11) -0.0028(9) -0.0019(10) C11 0.0236(11) 0.0197(11) 0.0263(11) 0.0038(9) -0.0003(9) 0.0018(9) C37 0.0240(11) 0.0313(13) 0.0281(12) -0.0042(10) 0.0028(9) -0.0007(10) C28 0.0324(13) 0.0402(15) 0.0323(13) 0.0049(11) -0.0037(10) -0.0091(11) C12 0.0335(13) 0.0232(11) 0.0252(12) -0.0025(9) -0.0022(10) 0.0014(10) C19 0.0268(12) 0.0385(14) 0.0241(12) 0.0002(10) -0.0014(9) 0.0070(10) C30 0.0218(11) 0.0307(12) 0.0260(12) 0.0057(10) 0.0040(9) 0.0021(9) C13 0.0308(12) 0.0262(12) 0.0206(11) 0.0009(9) 0.0022(9) 0.0028(10) C25 0.0339(13) 0.0436(15) 0.0297(13) -0.0100(11) 0.0094(10) -0.0135(11) C26 0.0499(16) 0.0483(16) 0.0221(12) -0.0080(11) 0.0087(11) -0.0199(13) C34 0.0241(12) 0.0243(13) 0.0485(15) -0.0059(11) 0.0124(11) -0.0040(10) C46 0.0332(14) 0.0602(18) 0.0314(14) -0.0111(13) 0.0076(11) -0.0157(13) C21 0.0349(13) 0.0302(13) 0.0416(15) 0.0084(11) -0.0073(11) 0.0034(11) C40 0.0327(13) 0.0310(14) 0.0516(17) -0.0001(12) -0.0018(12) 0.0053(11) C23 0.0479(15) 0.0387(14) 0.0242(12) -0.0025(11) 0.0074(11) 0.0024(12) C22 0.0337(13) 0.0340(13) 0.0292(13) 0.0068(10) -0.0020(10) 0.0007(11) C27 0.0494(16) 0.0503(17) 0.0245(13) 0.0038(12) -0.0074(11) -0.0181(14) C44 0.0497(16) 0.0418(15) 0.0390(15) -0.0017(12) 0.0259(13) -0.0019(13) C42 0.0381(15) 0.0303(14) 0.0587(18) -0.0082(13) 0.0070(13) 0.0067(11) C45 0.0328(14) 0.0556(17) 0.0342(14) -0.0111(13) 0.0147(11) -0.0120(12) C39 0.0491(16) 0.0287(13) 0.0389(15) -0.0101(11) -0.0084(12) 0.0127(12) C41 0.0428(15) 0.0399(15) 0.0402(15) -0.0028(12) 0.0115(12) 0.0048(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.357(3) . ? O1 C16 1.459(3) . ? O6 C38 1.363(3) . ? O6 C39 1.454(3) . ? O5 C11 1.227(3) . ? O4 C20 1.338(3) . ? O4 C21 1.448(3) . ? O3 C20 1.208(3) . ? O9 C43 1.339(3) . ? O9 C44 1.441(3) . ? O2 C2 1.378(3) . ? O2 C19 1.444(3) . ? O8 C43 1.203(3) . ? O7 C25 1.376(3) . ? O7 C42 1.519(3) . ? O10 C34 1.230(3) . ? C38 C33 1.344(3) . ? C38 C37 1.504(3) . ? C10 C15 1.354(3) . ? C10 C11 1.465(3) . ? C10 C9 1.512(3) . ? C15 C14 1.499(3) . ? C43 C31 1.495(3) . ? C2 C1 1.385(3) . ? C2 C3 1.392(3) . ? C31 C30 1.337(3) . ? C31 C32 1.515(3) . ? C9 C8 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C20 C8 1.487(3) . ? C1 C6 1.393(3) . ? C1 H1 0.9500 . ? C8 C7 1.343(3) . ? C4 C3 1.379(4) . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C14 C13 1.534(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C3 H3 0.9500 . ? C29 C24 1.393(3) . ? C29 C28 1.396(3) . ? C29 C30 1.481(3) . ? C7 C6 1.474(3) . ? C7 H7 0.9500 . ? C5 C6 1.397(3) . ? C5 H5 0.9500 . ? C17 C18 1.322(3) . ? C17 C16 1.499(3) . ? C17 H17 0.9500 . ? C32 C33 1.508(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C36 C35 1.524(4) . ? C36 C46 1.526(3) . ? C36 C37 1.532(3) . ? C36 C45 1.536(3) . ? C35 C34 1.515(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C33 C34 1.464(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C24 C25 1.392(3) . ? C24 H24 0.9500 . ? C18 C19 1.495(4) . ? C18 H18 0.9500 . ? C11 C12 1.511(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C28 C27 1.386(4) . ? C28 H28 0.9500 . ? C12 C13 1.525(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C30 H30 0.9500 . ? C13 C23 1.528(3) . ? C13 C22 1.530(3) . ? C25 C26 1.390(4) . ? C26 C27 1.383(4) . ? C26 H26 0.9500 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C40 C41 1.349(4) . ? C40 C39 1.432(4) . ? C40 H40 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C27 H27 0.9500 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C42 C41 1.468(4) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C41 H41 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 C15 O1 C16 119.08(17) . . ? C38 O6 C39 118.98(18) . . ? C20 O4 C21 115.06(18) . . ? C43 O9 C44 115.90(19) . . ? C2 O2 C19 116.55(17) . . ? C25 O7 C42 117.50(19) . . ? C33 C38 O6 117.58(19) . . ? C33 C38 C37 124.8(2) . . ? O6 C38 C37 117.45(19) . . ? C15 C10 C11 118.97(19) . . ? C15 C10 C9 124.15(19) . . ? C11 C10 C9 116.62(18) . . ? C10 C15 O1 117.51(19) . . ? C10 C15 C14 124.22(19) . . ? O1 C15 C14 118.26(18) . . ? O8 C43 O9 123.1(2) . . ? O8 C43 C31 124.0(2) . . ? O9 C43 C31 112.95(19) . . ? O2 C2 C1 123.0(2) . . ? O2 C2 C3 117.3(2) . . ? C1 C2 C3 119.7(2) . . ? C30 C31 C43 118.5(2) . . ? C30 C31 C32 125.6(2) . . ? C43 C31 C32 115.52(19) . . ? C10 C9 C8 117.09(18) . . ? C10 C9 H9A 108.0 . . ? C8 C9 H9A 108.0 . . ? C10 C9 H9B 108.0 . . ? C8 C9 H9B 108.0 . . ? H9A C9 H9B 107.3 . . ? O3 C20 O4 122.9(2) . . ? O3 C20 C8 123.3(2) . . ? O4 C20 C8 113.71(19) . . ? C2 C1 C6 121.0(2) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C7 C8 C20 120.0(2) . . ? C7 C8 C9 125.4(2) . . ? C20 C8 C9 113.60(18) . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C15 C14 C13 113.48(18) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C24 C29 C28 119.4(2) . . ? C24 C29 C30 121.3(2) . . ? C28 C29 C30 119.1(2) . . ? C8 C7 C6 126.4(2) . . ? C8 C7 H7 116.8 . . ? C6 C7 H7 116.8 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C18 C17 C16 125.3(2) . . ? C18 C17 H17 117.4 . . ? C16 C17 H17 117.4 . . ? C33 C32 C31 115.51(18) . . ? C33 C32 H32A 108.4 . . ? C31 C32 H32A 108.4 . . ? C33 C32 H32B 108.4 . . ? C31 C32 H32B 108.4 . . ? H32A C32 H32B 107.5 . . ? C1 C6 C5 118.9(2) . . ? C1 C6 C7 119.2(2) . . ? C5 C6 C7 121.8(2) . . ? C35 C36 C46 111.0(2) . . ? C35 C36 C37 108.25(19) . . ? C46 C36 C37 109.2(2) . . ? C35 C36 C45 109.3(2) . . ? C46 C36 C45 108.4(2) . . ? C37 C36 C45 110.7(2) . . ? C34 C35 C36 115.39(19) . . ? C34 C35 H35A 108.4 . . ? C36 C35 H35A 108.4 . . ? C34 C35 H35B 108.4 . . ? C36 C35 H35B 108.4 . . ? H35A C35 H35B 107.5 . . ? C38 C33 C34 118.6(2) . . ? C38 C33 C32 122.9(2) . . ? C34 C33 C32 118.2(2) . . ? O1 C16 C17 107.88(18) . . ? O1 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? O1 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C25 C24 C29 120.1(2) . . ? C25 C24 H24 119.9 . . ? C29 C24 H24 119.9 . . ? C17 C18 C19 126.9(2) . . ? C17 C18 H18 116.6 . . ? C19 C18 H18 116.6 . . ? O5 C11 C10 121.6(2) . . ? O5 C11 C12 119.8(2) . . ? C10 C11 C12 118.43(19) . . ? C38 C37 C36 111.79(19) . . ? C38 C37 H37A 109.3 . . ? C36 C37 H37A 109.3 . . ? C38 C37 H37B 109.3 . . ? C36 C37 H37B 109.3 . . ? H37A C37 H37B 107.9 . . ? C27 C28 C29 120.0(3) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C11 C12 C13 114.18(19) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O2 C19 C18 111.0(2) . . ? O2 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? O2 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C31 C30 C29 129.0(2) . . ? C31 C30 H30 115.5 . . ? C29 C30 H30 115.5 . . ? C12 C13 C23 110.3(2) . . ? C12 C13 C22 110.39(19) . . ? C23 C13 C22 109.07(19) . . ? C12 C13 C14 108.27(18) . . ? C23 C13 C14 108.70(19) . . ? C22 C13 C14 110.05(19) . . ? O7 C25 C26 115.7(2) . . ? O7 C25 C24 124.2(2) . . ? C26 C25 C24 120.1(2) . . ? C27 C26 C25 119.6(2) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? O10 C34 C33 121.5(2) . . ? O10 C34 C35 119.8(2) . . ? C33 C34 C35 118.5(2) . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C41 C40 C39 125.6(3) . . ? C41 C40 H40 117.2 . . ? C39 C40 H40 117.2 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C13 C22 H22A 109.5 . . ? C13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C26 C27 C28 120.7(2) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? O9 C44 H44A 109.5 . . ? O9 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O9 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C41 C42 O7 109.2(2) . . ? C41 C42 H42A 109.8 . . ? O7 C42 H42A 109.8 . . ? C41 C42 H42B 109.8 . . ? O7 C42 H42B 109.8 . . ? H42A C42 H42B 108.3 . . ? C36 C45 H45A 109.5 . . ? C36 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C36 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C40 C39 O6 108.1(2) . . ? C40 C39 H39A 110.1 . . ? O6 C39 H39A 110.1 . . ? C40 C39 H39B 110.1 . . ? O6 C39 H39B 110.1 . . ? H39A C39 H39B 108.4 . . ? C40 C41 C42 125.5(3) . . ? C40 C41 H41 117.2 . . ? C42 C41 H41 117.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.143 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 917201' ####################################################################### # # 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_global #===END data_7g #TrackingRef 'scif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4E,16E)-2,8-Dioxa-16-methoxycarbonyltricyclo[16.3.1.09,14]docosane-1(22),4,9(14),16,18,20-hexaen-13-one ; _chemical_name_common macrocycle _chemical_melting_point 393(2) _chemical_formula_moiety 'C22 H24 O5' _chemical_formula_sum 'C22 H24 O5' _chemical_formula_weight 368.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.8167(12) _cell_length_b 8.2210(6) _cell_length_c 15.9694(12) _cell_angle_alpha 90.00 _cell_angle_beta 116.3120(10) _cell_angle_gamma 90.00 _cell_volume 1861.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8506 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.94 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12844 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.96 _reflns_number_total 3615 _reflns_number_gt 3180 _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^)+(0.0759P)^2^+0.4714P] 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 3615 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1315 _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 O1 O 0.02587(8) 0.56126(14) 0.22535(7) 0.0447(3) Uani 1 1 d . . . O2 O -0.14571(8) 0.22002(14) 0.35864(9) 0.0487(3) Uani 1 1 d . . . O5 O 0.38774(8) 0.33589(14) 0.58511(8) 0.0498(3) Uani 1 1 d . . . O4 O 0.34155(9) 0.59006(15) 0.54048(10) 0.0577(4) Uani 1 1 d . . . O3 O 0.33820(8) 0.39659(19) 0.37385(9) 0.0590(4) Uani 1 1 d . . . C2 C -0.05914(10) 0.15222(19) 0.38132(11) 0.0374(3) Uani 1 1 d . . . C7 C 0.20306(10) 0.23775(19) 0.49150(10) 0.0359(3) Uani 1 1 d . . . H7 H 0.2489 0.1830 0.5423 0.043 Uiso 1 1 calc R . . C6 C 0.11042(10) 0.15436(19) 0.44459(10) 0.0354(3) Uani 1 1 d . . . C10 C 0.17822(10) 0.46959(17) 0.30116(10) 0.0332(3) Uani 1 1 d . . . C1 C 0.02544(10) 0.23619(19) 0.42102(10) 0.0379(3) Uani 1 1 d . . . H1 H 0.0257 0.3473 0.4320 0.045 Uiso 1 1 calc R . . C21 C 0.32451(10) 0.44750(19) 0.53364(10) 0.0368(3) Uani 1 1 d . . . C4 C 0.02314(12) -0.0937(2) 0.38650(12) 0.0455(4) Uani 1 1 d . . . H4 H 0.0225 -0.2044 0.3742 0.055 Uiso 1 1 calc R . . C15 C 0.10299(11) 0.50472(18) 0.21948(10) 0.0366(3) Uani 1 1 d . . . C3 C -0.06057(12) -0.0122(2) 0.36246(12) 0.0434(4) Uani 1 1 d . . . H3 H -0.1177 -0.0674 0.3337 0.052 Uiso 1 1 calc R . . C8 C 0.22988(10) 0.38014(18) 0.47105(9) 0.0327(3) Uani 1 1 d . . . C11 C 0.26789(11) 0.4267(2) 0.30199(11) 0.0405(4) Uani 1 1 d . . . C5 C 0.10832(11) -0.01161(19) 0.42884(11) 0.0404(4) Uani 1 1 d . . . H5 H 0.1645 -0.0684 0.4468 0.048 Uiso 1 1 calc R . . C17 C -0.13628(12) 0.6101(2) 0.17867(12) 0.0469(4) Uani 1 1 d . . . H17A H -0.1217 0.7139 0.2108 0.056 Uiso 1 1 calc R . . H17B H -0.1979 0.6192 0.1256 0.056 Uiso 1 1 calc R . . C16 C -0.06398(11) 0.5747(2) 0.14362(11) 0.0448(4) Uani 1 1 d . . . H16A H -0.0790 0.4741 0.1083 0.054 Uiso 1 1 calc R . . H16B H -0.0623 0.6621 0.1035 0.054 Uiso 1 1 calc R . . C14 C 0.10190(13) 0.4900(2) 0.12517(11) 0.0499(4) Uani 1 1 d . . . H14A H 0.1060 0.5976 0.1023 0.060 Uiso 1 1 calc R . . H14B H 0.0428 0.4415 0.0816 0.060 Uiso 1 1 calc R . . C18 C -0.14019(11) 0.4822(2) 0.24361(12) 0.0459(4) Uani 1 1 d . . . H18 H -0.1407 0.3743 0.2259 0.055 Uiso 1 1 calc R . . C9 C 0.17014(10) 0.49217(18) 0.39171(10) 0.0357(3) Uani 1 1 d . . . H9A H 0.1870 0.6035 0.4124 0.043 Uiso 1 1 calc R . . H9B H 0.1046 0.4772 0.3787 0.043 Uiso 1 1 calc R . . C12 C 0.27391(14) 0.4283(3) 0.21021(13) 0.0605(5) Uani 1 1 d . . . H12A H 0.2933 0.5357 0.2004 0.073 Uiso 1 1 calc R . . H12B H 0.3219 0.3515 0.2135 0.073 Uiso 1 1 calc R . . C22 C 0.47934(13) 0.3992(3) 0.64792(15) 0.0659(6) Uani 1 1 d . . . H22A H 0.5099 0.4418 0.6124 0.099 Uiso 1 1 calc R . . H22B H 0.5171 0.3135 0.6878 0.099 Uiso 1 1 calc R . . H22C H 0.4720 0.4843 0.6853 0.099 Uiso 1 1 calc R . . C19 C -0.14292(12) 0.5091(2) 0.32334(13) 0.0477(4) Uani 1 1 d . . . H19 H -0.1404 0.6170 0.3418 0.057 Uiso 1 1 calc R . . C20 C -0.14965(12) 0.3825(2) 0.38730(14) 0.0490(4) Uani 1 1 d . . . H20A H -0.0985 0.3987 0.4492 0.059 Uiso 1 1 calc R . . H20B H -0.2084 0.3974 0.3916 0.059 Uiso 1 1 calc R . . C13 C 0.18363(15) 0.3862(3) 0.12963(14) 0.0684(6) Uani 1 1 d . . . H13A H 0.1696 0.2725 0.1339 0.082 Uiso 1 1 calc R . . H13B H 0.1900 0.4007 0.0724 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0334(6) 0.0572(7) 0.0353(6) 0.0010(5) 0.0079(5) 0.0109(5) O2 0.0332(6) 0.0449(7) 0.0706(8) -0.0084(6) 0.0254(6) -0.0064(5) O5 0.0305(6) 0.0469(7) 0.0544(7) 0.0048(5) 0.0028(5) -0.0028(5) O4 0.0446(7) 0.0398(7) 0.0726(8) -0.0084(6) 0.0115(6) -0.0068(5) O3 0.0340(6) 0.0947(10) 0.0485(7) 0.0072(7) 0.0186(6) 0.0103(6) C2 0.0321(7) 0.0422(8) 0.0413(8) -0.0027(6) 0.0192(6) -0.0045(6) C7 0.0301(7) 0.0411(8) 0.0343(7) 0.0030(6) 0.0125(6) 0.0008(6) C6 0.0335(7) 0.0405(8) 0.0333(7) 0.0009(6) 0.0159(6) -0.0043(6) C10 0.0322(7) 0.0334(7) 0.0343(7) 0.0006(6) 0.0149(6) -0.0018(6) C1 0.0363(8) 0.0348(8) 0.0449(8) -0.0046(6) 0.0202(7) -0.0055(6) C21 0.0328(8) 0.0390(8) 0.0378(7) -0.0027(6) 0.0149(6) -0.0014(6) C4 0.0490(9) 0.0355(8) 0.0540(9) -0.0047(7) 0.0247(8) -0.0050(7) C15 0.0362(8) 0.0351(8) 0.0365(8) 0.0009(6) 0.0143(6) 0.0005(6) C3 0.0401(8) 0.0408(9) 0.0497(9) -0.0073(7) 0.0202(7) -0.0121(7) C8 0.0283(7) 0.0384(8) 0.0319(7) -0.0014(6) 0.0137(6) 0.0011(6) C11 0.0353(8) 0.0465(9) 0.0418(8) 0.0010(7) 0.0189(7) 0.0002(7) C5 0.0398(8) 0.0402(8) 0.0436(8) 0.0035(6) 0.0209(7) 0.0019(6) C17 0.0351(8) 0.0448(9) 0.0486(9) -0.0004(7) 0.0074(7) 0.0099(7) C16 0.0376(9) 0.0461(9) 0.0378(8) 0.0036(7) 0.0049(7) 0.0081(7) C14 0.0486(10) 0.0633(11) 0.0350(8) 0.0025(7) 0.0159(7) 0.0027(8) C18 0.0352(8) 0.0402(9) 0.0539(10) -0.0057(7) 0.0122(7) 0.0025(7) C9 0.0317(7) 0.0398(8) 0.0353(7) 0.0030(6) 0.0148(6) 0.0041(6) C12 0.0525(11) 0.0874(15) 0.0503(10) 0.0033(10) 0.0307(9) 0.0108(10) C22 0.0326(9) 0.0696(13) 0.0700(13) -0.0051(10) -0.0004(9) -0.0037(9) C19 0.0404(9) 0.0400(9) 0.0652(11) -0.0102(8) 0.0258(8) -0.0005(7) C20 0.0403(9) 0.0492(10) 0.0668(11) -0.0113(8) 0.0322(8) -0.0029(7) C13 0.0585(12) 0.1045(17) 0.0459(10) -0.0103(10) 0.0266(9) 0.0062(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.3468(19) . ? O1 C16 1.4460(18) . ? O2 C2 1.3701(19) . ? O2 C20 1.423(2) . ? O5 C21 1.3375(19) . ? O5 C22 1.445(2) . ? O4 C21 1.1967(19) . ? O3 C11 1.2179(19) . ? C2 C3 1.383(2) . ? C2 C1 1.384(2) . ? C7 C8 1.334(2) . ? C7 C6 1.485(2) . ? C7 H7 0.9300 . ? C6 C5 1.385(2) . ? C6 C1 1.397(2) . ? C10 C15 1.351(2) . ? C10 C11 1.456(2) . ? C10 C9 1.5184(19) . ? C1 H1 0.9300 . ? C21 C8 1.490(2) . ? C4 C3 1.378(2) . ? C4 C5 1.386(2) . ? C4 H4 0.9300 . ? C15 C14 1.503(2) . ? C3 H3 0.9300 . ? C8 C9 1.512(2) . ? C11 C12 1.510(2) . ? C5 H5 0.9300 . ? C17 C18 1.497(3) . ? C17 C16 1.508(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C14 C13 1.524(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C18 C19 1.312(3) . ? C18 H18 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C12 C13 1.478(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C19 C20 1.494(3) . ? C19 H19 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? 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 C15 O1 C16 121.44(12) . . ? C2 O2 C20 118.57(12) . . ? C21 O5 C22 115.22(14) . . ? O2 C2 C3 114.97(13) . . ? O2 C2 C1 124.60(14) . . ? C3 C2 C1 120.43(14) . . ? C8 C7 C6 129.15(14) . . ? C8 C7 H7 115.4 . . ? C6 C7 H7 115.4 . . ? C5 C6 C1 118.85(14) . . ? C5 C6 C7 119.03(14) . . ? C1 C6 C7 122.00(14) . . ? C15 C10 C11 119.89(13) . . ? C15 C10 C9 118.91(13) . . ? C11 C10 C9 120.92(13) . . ? C2 C1 C6 120.15(14) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? O4 C21 O5 122.61(14) . . ? O4 C21 C8 122.94(14) . . ? O5 C21 C8 114.37(13) . . ? C3 C4 C5 120.35(15) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? O1 C15 C10 116.35(13) . . ? O1 C15 C14 119.27(13) . . ? C10 C15 C14 124.34(14) . . ? C4 C3 C2 119.59(15) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C7 C8 C21 119.72(13) . . ? C7 C8 C9 126.25(13) . . ? C21 C8 C9 113.88(13) . . ? O3 C11 C10 122.46(14) . . ? O3 C11 C12 119.48(15) . . ? C10 C11 C12 117.98(14) . . ? C6 C5 C4 120.55(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C18 C17 C16 113.15(14) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.8 . . ? O1 C16 C17 106.46(13) . . ? O1 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? O1 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C15 C14 C13 111.44(14) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C19 C18 C17 125.71(16) . . ? C19 C18 H18 117.1 . . ? C17 C18 H18 117.1 . . ? C8 C9 C10 116.01(12) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C13 C12 C11 112.99(16) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? O5 C22 H22A 109.5 . . ? O5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C19 C20 126.11(16) . . ? C18 C19 H19 116.9 . . ? C20 C19 H19 116.9 . . ? O2 C20 C19 114.04(14) . . ? O2 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? O2 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C12 C13 C14 112.43(17) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.457 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 915413'