# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_110309 #TrackingRef '110309.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N2 O5' _chemical_formula_weight 390.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 12.5002(2) _cell_length_b 21.1067(3) _cell_length_c 7.44870(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.576(2) _cell_angle_gamma 90.00 _cell_volume 1893.08(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 8237 _cell_measurement_theta_min 3.6677 _cell_measurement_theta_max 69.3583 _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 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7364 _exptl_absorpt_correction_T_max 0.7921 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16272 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 69.49 _reflns_number_total 3516 _reflns_number_gt 3038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0685P)^2^+0.4720P] 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 3516 _refine_ls_number_parameters 263 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.573 _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 0.10265(15) 0.02137(9) 0.6691(3) 0.0610(5) Uani 1 1 d . . . O3 O 0.38061(15) 0.06083(9) 0.3950(2) 0.0590(5) Uani 1 1 d . . . O1 O 0.26399(16) 0.21001(8) 0.8466(3) 0.0555(5) Uani 1 1 d . . . N1 N 0.24554(16) 0.02638(9) 0.5299(3) 0.0457(5) Uani 1 1 d . . . C17 C 0.25465(19) -0.03995(11) 0.4977(3) 0.0460(5) Uani 1 1 d . . . C15 C 0.17131(18) 0.05214(12) 0.6215(3) 0.0460(5) Uani 1 1 d . . . C12 C 0.1945(2) 0.12252(11) 0.6476(3) 0.0457(5) Uani 1 1 d . . . H12 H 0.1276 0.1468 0.5872 0.055 Uiso 1 1 calc R . . C8 C 0.3450(2) 0.10690(12) 0.9402(3) 0.0489(6) Uani 1 1 d . . . H8 H 0.3541 0.0807 1.0435 0.059 Uiso 1 1 calc R . . C7 C 0.2390(2) 0.14316(11) 0.8573(3) 0.0464(5) Uani 1 1 d . . . C21 C 0.1752(2) -0.13771(13) 0.3683(5) 0.0657(8) Uani 1 1 d . . . H21 H 0.1149 -0.1613 0.3007 0.079 Uiso 1 1 calc R . . C10 C 0.3907(2) 0.16146(12) 0.6929(3) 0.0504(6) Uani 1 1 d . . . H10 H 0.4515 0.1689 0.6355 0.061 Uiso 1 1 calc R . . C4 C 0.1519(2) 0.13928(12) 0.9643(3) 0.0496(6) Uani 1 1 d . . . C3 C 0.0911(2) 0.19260(14) 0.9849(4) 0.0631(7) Uani 1 1 d . . . H3 H 0.1052 0.2310 0.9344 0.076 Uiso 1 1 calc R . . C18 C 0.3565(2) -0.06884(13) 0.5672(4) 0.0540(6) Uani 1 1 d . . . H18 H 0.4172 -0.0453 0.6334 0.065 Uiso 1 1 calc R . . C9 C 0.4242(2) 0.11536(12) 0.8538(3) 0.0497(6) Uani 1 1 d . . . C22 C 0.1634(2) -0.07440(13) 0.4014(4) 0.0617(7) Uani 1 1 d . . . H22 H 0.0945 -0.0549 0.3592 0.074 Uiso 1 1 calc R . . C13 C 0.3555(2) 0.22253(12) 0.7702(4) 0.0568(6) Uani 1 1 d . . . H13B H 0.4173 0.2395 0.8663 0.068 Uiso 1 1 calc R . . H13A H 0.3340 0.2538 0.6715 0.068 Uiso 1 1 calc R . . C11 C 0.2862(2) 0.13529(11) 0.5499(3) 0.0476(6) Uani 1 1 d . . . H11 H 0.2602 0.1651 0.4465 0.057 Uiso 1 1 calc R . . C16 C 0.31231(19) 0.07206(12) 0.4791(3) 0.0467(5) Uani 1 1 d . . . C5 C 0.1288(2) 0.08261(14) 1.0429(4) 0.0586(7) Uani 1 1 d . . . H5 H 0.1690 0.0463 1.0333 0.070 Uiso 1 1 calc R . . O5 O 0.2123(2) -0.26117(12) 0.2980(5) 0.0991(8) Uani 1 1 d U . . N2 N 0.2900(2) -0.23281(13) 0.3972(5) 0.0796(8) Uani 1 1 d U . . C6 C 0.0460(3) 0.08016(17) 1.1354(4) 0.0698(8) Uani 1 1 d . . . H6 H 0.0306 0.0420 1.1857 0.084 Uiso 1 1 calc R . . C19 C 0.3680(2) -0.13249(13) 0.5383(4) 0.0602(7) Uani 1 1 d . . . H19 H 0.4358 -0.1527 0.5866 0.072 Uiso 1 1 calc R . . C20 C 0.2773(2) -0.16567(13) 0.4363(4) 0.0575(6) Uani 1 1 d U . . C14 C 0.5373(2) 0.08610(15) 0.9035(4) 0.0645(7) Uani 1 1 d . . . H14A H 0.5472 0.0624 0.7991 0.097 Uiso 1 1 calc R . . H14C H 0.5448 0.0583 1.0081 0.097 Uiso 1 1 calc R . . H14B H 0.5925 0.1188 0.9352 0.097 Uiso 1 1 calc R . . C2 C 0.0099(3) 0.18943(18) 1.0797(5) 0.0762(9) Uani 1 1 d . . . H2 H -0.0293 0.2257 1.0933 0.091 Uiso 1 1 calc R . . O4 O 0.3785(3) -0.25726(15) 0.4631(6) 0.1407(12) Uani 1 1 d U . . C1 C -0.0130(3) 0.13336(19) 1.1533(5) 0.0764(9) Uani 1 1 d . . . H1 H -0.0683 0.1313 1.2153 0.092 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 0.0562(10) 0.0608(11) 0.0729(12) -0.0119(9) 0.0292(9) -0.0153(9) O3 0.0583(11) 0.0675(12) 0.0573(10) -0.0018(8) 0.0258(9) -0.0051(9) O1 0.0657(11) 0.0414(9) 0.0622(10) -0.0039(7) 0.0222(8) -0.0061(8) N1 0.0444(10) 0.0453(11) 0.0483(10) -0.0032(8) 0.0141(8) -0.0028(8) C17 0.0456(12) 0.0472(13) 0.0459(12) -0.0016(10) 0.0136(9) -0.0016(10) C15 0.0413(12) 0.0510(13) 0.0445(12) -0.0036(10) 0.0095(9) -0.0026(10) C12 0.0472(12) 0.0445(12) 0.0434(12) 0.0018(9) 0.0086(9) 0.0021(10) C8 0.0521(13) 0.0492(13) 0.0424(12) 0.0029(10) 0.0075(10) -0.0043(10) C7 0.0524(13) 0.0402(12) 0.0457(12) -0.0014(9) 0.0114(10) -0.0040(10) C21 0.0519(15) 0.0534(16) 0.086(2) -0.0116(14) 0.0089(14) -0.0079(12) C10 0.0513(13) 0.0488(13) 0.0514(13) 0.0018(10) 0.0142(10) -0.0082(10) C4 0.0504(13) 0.0531(14) 0.0441(12) -0.0044(10) 0.0105(10) -0.0031(11) C3 0.0595(16) 0.0584(16) 0.0719(17) -0.0088(13) 0.0186(13) -0.0027(12) C18 0.0440(13) 0.0585(15) 0.0565(14) -0.0063(11) 0.0084(10) -0.0002(11) C9 0.0497(13) 0.0483(13) 0.0472(12) -0.0013(10) 0.0064(10) -0.0051(10) C22 0.0447(13) 0.0526(15) 0.0802(18) -0.0050(13) 0.0039(12) 0.0018(11) C13 0.0637(16) 0.0460(13) 0.0609(15) 0.0009(11) 0.0169(12) -0.0104(12) C11 0.0533(13) 0.0464(13) 0.0416(11) 0.0063(9) 0.0102(10) -0.0017(10) C16 0.0456(12) 0.0532(14) 0.0397(11) 0.0022(9) 0.0088(9) -0.0043(10) C5 0.0606(16) 0.0623(16) 0.0536(14) 0.0054(12) 0.0163(12) -0.0022(13) O5 0.0913(13) 0.0646(13) 0.1433(19) -0.0276(13) 0.0349(12) -0.0132(11) N2 0.0711(13) 0.0541(13) 0.116(2) -0.0109(13) 0.0299(13) 0.0033(10) C6 0.0627(17) 0.090(2) 0.0574(16) 0.0116(15) 0.0170(13) -0.0121(16) C19 0.0481(14) 0.0603(16) 0.0707(17) -0.0008(13) 0.0135(12) 0.0083(12) C20 0.0570(14) 0.0498(11) 0.0700(16) -0.0018(11) 0.0246(12) 0.0005(10) C14 0.0519(15) 0.0710(18) 0.0659(16) 0.0059(14) 0.0077(12) 0.0008(13) C2 0.0635(18) 0.084(2) 0.086(2) -0.0190(18) 0.0281(16) 0.0021(16) O4 0.1048(15) 0.0762(15) 0.216(3) -0.0229(17) -0.0009(17) 0.0342(13) C1 0.0583(17) 0.108(3) 0.0673(18) -0.0078(18) 0.0249(14) -0.0031(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 C15 1.203(3) . ? O3 C16 1.210(3) . ? O1 C13 1.433(3) . ? O1 C7 1.452(3) . ? N1 C16 1.393(3) . ? N1 C15 1.401(3) . ? N1 C17 1.430(3) . ? C17 C22 1.380(4) . ? C17 C18 1.381(3) . ? C15 C12 1.516(3) . ? C12 C11 1.538(3) . ? C12 C7 1.572(3) . ? C12 H12 0.9800 . ? C8 C9 1.330(4) . ? C8 C7 1.510(3) . ? C8 H8 0.9300 . ? C7 C4 1.515(3) . ? C21 C20 1.373(4) . ? C21 C22 1.374(4) . ? C21 H21 0.9300 . ? C10 C9 1.513(3) . ? C10 C13 1.524(4) . ? C10 C11 1.549(3) . ? C10 H10 0.9800 . ? C4 C3 1.389(4) . ? C4 C5 1.395(4) . ? C3 C2 1.385(4) . ? C3 H3 0.9300 . ? C18 C19 1.374(4) . ? C18 H18 0.9300 . ? C9 C14 1.495(4) . ? C22 H22 0.9300 . ? C13 H13B 0.9700 . ? C13 H13A 0.9700 . ? C11 C16 1.503(3) . ? C11 H11 0.9800 . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? O5 N2 1.210(4) . ? N2 O4 1.199(4) . ? N2 C20 1.464(4) . ? C6 C1 1.370(5) . ? C6 H6 0.9300 . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C14 H14A 0.9600 . ? C14 H14C 0.9600 . ? C14 H14B 0.9600 . ? C2 C1 1.367(5) . ? C2 H2 0.9300 . ? C1 H1 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 C13 O1 C7 114.04(19) . . ? C16 N1 C15 112.8(2) . . ? C16 N1 C17 123.5(2) . . ? C15 N1 C17 123.7(2) . . ? C22 C17 C18 120.8(2) . . ? C22 C17 N1 120.7(2) . . ? C18 C17 N1 118.4(2) . . ? O2 C15 N1 123.5(2) . . ? O2 C15 C12 128.2(2) . . ? N1 C15 C12 108.32(19) . . ? C15 C12 C11 104.58(19) . . ? C15 C12 C7 113.81(19) . . ? C11 C12 C7 108.15(19) . . ? C15 C12 H12 110.0 . . ? C11 C12 H12 110.0 . . ? C7 C12 H12 110.0 . . ? C9 C8 C7 114.8(2) . . ? C9 C8 H8 122.6 . . ? C7 C8 H8 122.6 . . ? O1 C7 C8 109.71(19) . . ? O1 C7 C4 106.07(19) . . ? C8 C7 C4 115.6(2) . . ? O1 C7 C12 103.83(18) . . ? C8 C7 C12 107.67(19) . . ? C4 C7 C12 113.24(19) . . ? C20 C21 C22 119.0(3) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C9 C10 C13 106.9(2) . . ? C9 C10 C11 108.57(19) . . ? C13 C10 C11 106.6(2) . . ? C9 C10 H10 111.5 . . ? C13 C10 H10 111.5 . . ? C11 C10 H10 111.5 . . ? C3 C4 C5 117.9(3) . . ? C3 C4 C7 120.4(2) . . ? C5 C4 C7 121.7(2) . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C19 C18 C17 119.8(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C8 C9 C14 127.0(2) . . ? C8 C9 C10 112.7(2) . . ? C14 C9 C10 120.3(2) . . ? C21 C22 C17 119.5(2) . . ? C21 C22 H22 120.2 . . ? C17 C22 H22 120.2 . . ? O1 C13 C10 109.6(2) . . ? O1 C13 H13B 109.7 . . ? C10 C13 H13B 109.7 . . ? O1 C13 H13A 109.7 . . ? C10 C13 H13A 109.7 . . ? H13B C13 H13A 108.2 . . ? C16 C11 C12 105.69(19) . . ? C16 C11 C10 109.6(2) . . ? C12 C11 C10 109.57(19) . . ? C16 C11 H11 110.6 . . ? C12 C11 H11 110.6 . . ? C10 C11 H11 110.6 . . ? O3 C16 N1 124.3(2) . . ? O3 C16 C11 127.3(2) . . ? N1 C16 C11 108.5(2) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? O4 N2 O5 122.6(3) . . ? O4 N2 C20 118.2(3) . . ? O5 N2 C20 119.2(3) . . ? C1 C6 C5 120.7(3) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C18 C19 C20 118.6(2) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C21 C20 C19 122.1(3) . . ? C21 C20 N2 118.8(3) . . ? C19 C20 N2 119.0(3) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C1 C6 119.6(3) . . ? C2 C1 H1 120.2 . . ? C6 C1 H1 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C17 C22 -125.2(3) . . . . ? C15 N1 C17 C22 57.1(3) . . . . ? C16 N1 C17 C18 55.6(3) . . . . ? C15 N1 C17 C18 -122.2(3) . . . . ? C16 N1 C15 O2 176.3(2) . . . . ? C17 N1 C15 O2 -5.8(4) . . . . ? C16 N1 C15 C12 -4.0(2) . . . . ? C17 N1 C15 C12 173.9(2) . . . . ? O2 C15 C12 C11 -177.0(2) . . . . ? N1 C15 C12 C11 3.3(2) . . . . ? O2 C15 C12 C7 65.2(3) . . . . ? N1 C15 C12 C7 -114.5(2) . . . . ? C13 O1 C7 C8 46.9(3) . . . . ? C13 O1 C7 C4 172.47(19) . . . . ? C13 O1 C7 C12 -67.9(2) . . . . ? C9 C8 C7 O1 -54.4(3) . . . . ? C9 C8 C7 C4 -174.3(2) . . . . ? C9 C8 C7 C12 57.9(3) . . . . ? C15 C12 C7 O1 175.18(19) . . . . ? C11 C12 C7 O1 59.5(2) . . . . ? C15 C12 C7 C8 58.9(3) . . . . ? C11 C12 C7 C8 -56.8(2) . . . . ? C15 C12 C7 C4 -70.2(3) . . . . ? C11 C12 C7 C4 174.04(19) . . . . ? O1 C7 C4 C3 17.7(3) . . . . ? C8 C7 C4 C3 139.5(2) . . . . ? C12 C7 C4 C3 -95.5(3) . . . . ? O1 C7 C4 C5 -163.1(2) . . . . ? C8 C7 C4 C5 -41.3(3) . . . . ? C12 C7 C4 C5 83.7(3) . . . . ? C5 C4 C3 C2 -0.3(4) . . . . ? C7 C4 C3 C2 178.9(2) . . . . ? C22 C17 C18 C19 0.9(4) . . . . ? N1 C17 C18 C19 -179.9(2) . . . . ? C7 C8 C9 C14 179.9(2) . . . . ? C7 C8 C9 C10 1.5(3) . . . . ? C13 C10 C9 C8 54.7(3) . . . . ? C11 C10 C9 C8 -59.9(3) . . . . ? C13 C10 C9 C14 -123.7(3) . . . . ? C11 C10 C9 C14 121.6(3) . . . . ? C20 C21 C22 C17 1.7(5) . . . . ? C18 C17 C22 C21 -2.5(4) . . . . ? N1 C17 C22 C21 178.3(3) . . . . ? C7 O1 C13 C10 8.7(3) . . . . ? C9 C10 C13 O1 -60.0(3) . . . . ? C11 C10 C13 O1 56.0(3) . . . . ? C15 C12 C11 C16 -1.6(2) . . . . ? C7 C12 C11 C16 120.0(2) . . . . ? C15 C12 C11 C10 -119.6(2) . . . . ? C7 C12 C11 C10 2.0(3) . . . . ? C9 C10 C11 C16 -60.5(3) . . . . ? C13 C10 C11 C16 -175.37(19) . . . . ? C9 C10 C11 C12 55.1(3) . . . . ? C13 C10 C11 C12 -59.8(2) . . . . ? C15 N1 C16 O3 -178.3(2) . . . . ? C17 N1 C16 O3 3.8(4) . . . . ? C15 N1 C16 C11 3.0(3) . . . . ? C17 N1 C16 C11 -175.0(2) . . . . ? C12 C11 C16 O3 -179.4(2) . . . . ? C10 C11 C16 O3 -61.4(3) . . . . ? C12 C11 C16 N1 -0.7(2) . . . . ? C10 C11 C16 N1 117.3(2) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C7 C4 C5 C6 -178.0(2) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C17 C18 C19 C20 1.4(4) . . . . ? C22 C21 C20 C19 0.6(5) . . . . ? C22 C21 C20 N2 -178.7(3) . . . . ? C18 C19 C20 C21 -2.2(5) . . . . ? C18 C19 C20 N2 177.1(3) . . . . ? O4 N2 C20 C21 -177.3(4) . . . . ? O5 N2 C20 C21 3.8(5) . . . . ? O4 N2 C20 C19 3.4(5) . . . . ? O5 N2 C20 C19 -175.5(3) . . . . ? C4 C3 C2 C1 -0.7(5) . . . . ? C3 C2 C1 C6 0.9(5) . . . . ? C5 C6 C1 C2 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 69.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.392 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 893862' ####################################################################### # # 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_110704 #TrackingRef '110704.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 O6' _chemical_formula_weight 330.32 _chemical_absolute_configuration unk 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.0858(3) _cell_length_b 10.4482(4) _cell_length_c 17.2738(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1639.81(10) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3513 _cell_measurement_theta_min 2.9651 _cell_measurement_theta_max 29.0736 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9685 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9191 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3353 _reflns_number_gt 2534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0358P)^2^+0.1446P] 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 ? _refine_ls_number_reflns 3353 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.51562(15) 0.44384(16) -0.00307(9) 0.0449(4) Uani 1 1 d . . . O3 O 0.80603(19) 0.28391(16) -0.15384(9) 0.0526(4) Uani 1 1 d . . . O6 O 0.29930(17) 0.59062(17) -0.14626(10) 0.0585(5) Uani 1 1 d . . . O1 O 0.92504(18) 0.38056(18) 0.11044(10) 0.0602(5) Uani 1 1 d . . . O4 O 0.8282(2) 0.43222(18) -0.24572(9) 0.0638(5) Uani 1 1 d . . . O5 O 0.23344(18) 0.4761(2) -0.04281(11) 0.0693(6) Uani 1 1 d . . . C13 C 0.4875(2) 0.4976(2) -0.07377(13) 0.0391(5) Uani 1 1 d . . . C12 C 0.5876(2) 0.5243(2) -0.12677(12) 0.0422(5) Uani 1 1 d . . . H12 H 0.5580 0.5634 -0.1726 0.051 Uiso 1 1 calc R . . C8 C 0.6667(2) 0.3558(2) 0.09104(12) 0.0442(6) Uani 1 1 d . . . H8B H 0.5934 0.3848 0.1279 0.053 Uiso 1 1 calc R . . H8A H 0.6345 0.2735 0.0715 0.053 Uiso 1 1 calc R . . C4 C 0.8075(2) 0.2568(2) 0.20620(11) 0.0402(5) Uani 1 1 d . . . C15 C 0.7554(3) 0.2776(2) -0.07322(12) 0.0468(6) Uani 1 1 d . . . H15B H 0.8152 0.2183 -0.0435 0.056 Uiso 1 1 calc R . . H15A H 0.6535 0.2503 -0.0707 0.056 Uiso 1 1 calc R . . C9 C 0.6696(2) 0.4502(2) 0.02349(11) 0.0400(5) Uani 1 1 d . . . C10 C 0.7723(2) 0.4135(2) -0.04261(12) 0.0393(5) Uani 1 1 d . . . H10 H 0.8742 0.4255 -0.0254 0.047 Uiso 1 1 calc R . . C11 C 0.7474(2) 0.4937(2) -0.11559(12) 0.0431(6) Uani 1 1 d . . . H11 H 0.8066 0.5721 -0.1142 0.052 Uiso 1 1 calc R . . C14 C 0.7989(2) 0.4055(3) -0.18002(13) 0.0470(6) Uani 1 1 d . . . C5 C 0.9412(3) 0.2230(2) 0.23870(14) 0.0502(6) Uani 1 1 d . . . H5 H 1.0284 0.2511 0.2162 0.060 Uiso 1 1 calc R . . C7 C 0.8101(3) 0.3363(2) 0.13405(12) 0.0415(5) Uani 1 1 d . . . C3 C 0.6790(3) 0.2149(2) 0.24099(13) 0.0515(6) Uani 1 1 d . . . H3 H 0.5884 0.2364 0.2195 0.062 Uiso 1 1 calc R . . C16 C 0.6995(3) 0.5871(2) 0.04981(14) 0.0574(7) Uani 1 1 d . . . H16B H 0.6748 0.6454 0.0089 0.086 Uiso 1 1 calc R . . H16C H 0.8018 0.5962 0.0626 0.086 Uiso 1 1 calc R . . H16A H 0.6407 0.6060 0.0946 0.086 Uiso 1 1 calc R . . C17 C 0.3264(3) 0.5197(2) -0.08411(13) 0.0434(5) Uani 1 1 d . . . C1 C 0.8177(3) 0.1070(3) 0.33898(15) 0.0687(8) Uani 1 1 d . . . H1 H 0.8214 0.0565 0.3833 0.082 Uiso 1 1 calc R . . C2 C 0.6841(3) 0.1414(3) 0.30750(15) 0.0666(8) Uani 1 1 d . . . H2 H 0.5971 0.1150 0.3310 0.080 Uiso 1 1 calc R . . C6 C 0.9458(3) 0.1481(3) 0.30421(15) 0.0625(8) Uani 1 1 d . . . H6 H 1.0363 0.1249 0.3252 0.075 Uiso 1 1 calc R . . C18 C 0.1464(3) 0.6135(3) -0.16411(16) 0.0656(8) Uani 1 1 d . . . H18C H 0.1393 0.6750 -0.2053 0.098 Uiso 1 1 calc R . . H18B H 0.0972 0.6460 -0.1190 0.098 Uiso 1 1 calc R . . H18A H 0.1009 0.5348 -0.1799 0.098 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(8) 0.0626(11) 0.0359(8) 0.0104(8) -0.0013(6) 0.0025(7) O3 0.0606(10) 0.0559(10) 0.0415(9) -0.0036(9) 0.0063(8) 0.0093(8) O6 0.0448(9) 0.0708(12) 0.0598(10) 0.0254(10) -0.0075(8) 0.0041(8) O1 0.0430(9) 0.0802(13) 0.0573(10) 0.0152(10) -0.0065(9) -0.0067(9) O4 0.0681(11) 0.0879(13) 0.0353(9) 0.0086(10) 0.0115(9) 0.0103(10) O5 0.0457(10) 0.0948(15) 0.0673(12) 0.0328(12) 0.0070(9) 0.0061(10) C13 0.0428(12) 0.0389(13) 0.0354(11) 0.0046(10) -0.0048(10) 0.0025(10) C12 0.0474(12) 0.0429(13) 0.0364(12) 0.0075(11) 0.0002(10) 0.0049(11) C8 0.0384(12) 0.0591(16) 0.0352(12) 0.0048(11) -0.0007(10) 0.0023(11) C4 0.0463(12) 0.0417(13) 0.0326(11) -0.0068(10) -0.0073(10) 0.0057(11) C15 0.0508(14) 0.0512(15) 0.0386(12) 0.0039(12) 0.0024(11) 0.0055(12) C9 0.0368(11) 0.0510(14) 0.0323(11) -0.0007(10) -0.0036(10) 0.0024(11) C10 0.0348(11) 0.0465(13) 0.0366(12) 0.0017(11) -0.0043(9) 0.0002(10) C11 0.0401(11) 0.0495(14) 0.0396(12) 0.0032(11) 0.0049(11) -0.0023(10) C14 0.0362(12) 0.0637(17) 0.0412(13) 0.0049(12) 0.0003(10) 0.0041(12) C5 0.0467(14) 0.0589(16) 0.0449(14) -0.0068(14) -0.0076(11) 0.0075(12) C7 0.0412(12) 0.0467(13) 0.0365(12) -0.0028(10) -0.0034(11) 0.0042(11) C3 0.0479(14) 0.0614(16) 0.0452(13) 0.0094(13) -0.0042(12) 0.0040(13) C16 0.0694(16) 0.0579(16) 0.0448(14) -0.0091(13) -0.0023(13) 0.0034(14) C17 0.0451(13) 0.0430(13) 0.0423(12) 0.0049(11) -0.0019(11) 0.0043(11) C1 0.088(2) 0.0702(19) 0.0475(15) 0.0147(15) -0.0103(16) 0.0085(18) C2 0.0691(18) 0.075(2) 0.0552(16) 0.0192(15) 0.0053(15) 0.0008(16) C6 0.0676(18) 0.0693(19) 0.0505(16) 0.0058(15) -0.0181(14) 0.0161(15) C18 0.0525(15) 0.0709(18) 0.0734(19) 0.0139(17) -0.0197(14) 0.0089(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C13 1.368(3) . ? O2 C9 1.474(2) . ? O3 C14 1.350(3) . ? O3 C15 1.468(3) . ? O6 C17 1.327(3) . ? O6 C18 1.443(3) . ? O1 C7 1.213(3) . ? O4 C14 1.199(3) . ? O5 C17 1.196(3) . ? C13 C12 1.320(3) . ? C13 C17 1.493(3) . ? C12 C11 1.499(3) . ? C12 H12 0.9300 . ? C8 C7 1.513(3) . ? C8 C9 1.528(3) . ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C4 C5 1.384(3) . ? C4 C3 1.385(3) . ? C4 C7 1.498(3) . ? C15 C10 1.523(3) . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? C9 C10 1.524(3) . ? C9 C16 1.526(3) . ? C10 C11 1.530(3) . ? C10 H10 0.9800 . ? C11 C14 1.519(3) . ? C11 H11 0.9800 . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C3 C2 1.383(3) . ? C3 H3 0.9300 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16 H16A 0.9600 . ? C1 C2 1.378(4) . ? C1 C6 1.379(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C18 H18C 0.9600 . ? C18 H18B 0.9600 . ? C18 H18A 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 C13 O2 C9 115.88(16) . . ? C14 O3 C15 110.20(18) . . ? C17 O6 C18 116.37(19) . . ? C12 C13 O2 125.25(19) . . ? C12 C13 C17 124.0(2) . . ? O2 C13 C17 110.69(18) . . ? C13 C12 C11 122.2(2) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C7 C8 C9 116.59(18) . . ? C7 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? H8B C8 H8A 107.3 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 C7 117.7(2) . . ? C3 C4 C7 123.3(2) . . ? O3 C15 C10 104.81(19) . . ? O3 C15 H15B 110.8 . . ? C10 C15 H15B 110.8 . . ? O3 C15 H15A 110.8 . . ? C10 C15 H15A 110.8 . . ? H15B C15 H15A 108.9 . . ? O2 C9 C10 109.69(16) . . ? O2 C9 C16 107.69(19) . . ? C10 C9 C16 110.48(19) . . ? O2 C9 C8 101.13(16) . . ? C10 C9 C8 114.87(18) . . ? C16 C9 C8 112.36(18) . . ? C15 C10 C9 115.64(19) . . ? C15 C10 C11 102.10(17) . . ? C9 C10 C11 112.90(17) . . ? C15 C10 H10 108.6 . . ? C9 C10 H10 108.6 . . ? C11 C10 H10 108.6 . . ? C12 C11 C14 109.47(19) . . ? C12 C11 C10 111.47(17) . . ? C14 C11 C10 103.05(18) . . ? C12 C11 H11 110.9 . . ? C14 C11 H11 110.9 . . ? C10 C11 H11 110.9 . . ? O4 C14 O3 121.7(2) . . ? O4 C14 C11 128.4(2) . . ? O3 C14 C11 109.90(18) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? O1 C7 C4 120.3(2) . . ? O1 C7 C8 121.6(2) . . ? C4 C7 C8 118.04(19) . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C9 C16 H16B 109.5 . . ? C9 C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? O5 C17 O6 124.3(2) . . ? O5 C17 C13 124.2(2) . . ? O6 C17 C13 111.43(19) . . ? C2 C1 C6 119.4(2) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O6 C18 H18C 109.5 . . ? O6 C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? O6 C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? H18B C18 H18A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O2 C13 C12 17.8(3) . . . . ? C9 O2 C13 C17 -163.49(18) . . . . ? O2 C13 C12 C11 2.0(4) . . . . ? C17 C13 C12 C11 -176.5(2) . . . . ? C14 O3 C15 C10 -21.5(2) . . . . ? C13 O2 C9 C10 -45.1(2) . . . . ? C13 O2 C9 C16 75.2(2) . . . . ? C13 O2 C9 C8 -166.77(17) . . . . ? C7 C8 C9 O2 179.97(18) . . . . ? C7 C8 C9 C10 62.0(3) . . . . ? C7 C8 C9 C16 -65.5(3) . . . . ? O3 C15 C10 C9 153.61(17) . . . . ? O3 C15 C10 C11 30.6(2) . . . . ? O2 C9 C10 C15 -62.5(2) . . . . ? C16 C9 C10 C15 178.88(19) . . . . ? C8 C9 C10 C15 50.5(2) . . . . ? O2 C9 C10 C11 54.5(2) . . . . ? C16 C9 C10 C11 -64.0(2) . . . . ? C8 C9 C10 C11 167.60(18) . . . . ? C13 C12 C11 C14 121.3(2) . . . . ? C13 C12 C11 C10 7.9(3) . . . . ? C15 C10 C11 C12 88.7(2) . . . . ? C9 C10 C11 C12 -36.1(3) . . . . ? C15 C10 C11 C14 -28.6(2) . . . . ? C9 C10 C11 C14 -153.39(18) . . . . ? C15 O3 C14 O4 -176.3(2) . . . . ? C15 O3 C14 C11 2.5(2) . . . . ? C12 C11 C14 O4 77.2(3) . . . . ? C10 C11 C14 O4 -164.1(2) . . . . ? C12 C11 C14 O3 -101.5(2) . . . . ? C10 C11 C14 O3 17.2(2) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C7 C4 C5 C6 -178.8(2) . . . . ? C5 C4 C7 O1 -7.9(3) . . . . ? C3 C4 C7 O1 172.8(2) . . . . ? C5 C4 C7 C8 170.4(2) . . . . ? C3 C4 C7 C8 -8.9(3) . . . . ? C9 C8 C7 O1 -8.9(3) . . . . ? C9 C8 C7 C4 172.88(18) . . . . ? C5 C4 C3 C2 0.5(3) . . . . ? C7 C4 C3 C2 179.8(2) . . . . ? C18 O6 C17 O5 -0.7(3) . . . . ? C18 O6 C17 C13 177.3(2) . . . . ? C12 C13 C17 O5 166.4(2) . . . . ? O2 C13 C17 O5 -12.3(3) . . . . ? C12 C13 C17 O6 -11.7(3) . . . . ? O2 C13 C17 O6 169.62(17) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? C4 C3 C2 C1 -1.2(4) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.126 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 893863' ####################################################################### # # 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_111009-gr #TrackingRef '111009-gr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 O6' _chemical_formula_weight 330.32 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.08020(10) _cell_length_b 10.4402(2) _cell_length_c 17.2659(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1636.79(4) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 10879 _cell_measurement_theta_min 4.2311 _cell_measurement_theta_max 71.8393 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7182 _exptl_absorpt_correction_T_max 0.7681 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12950 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 5.12 _diffrn_reflns_theta_max 71.96 _reflns_number_total 3124 _reflns_number_gt 3044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0465P)^2^+0.1221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0180(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(14) _refine_ls_number_reflns 3124 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.48416(9) 0.55646(9) 1.00316(5) 0.0451(2) Uani 1 1 d . . . O4 O 0.07500(11) 0.61943(11) 0.88943(6) 0.0607(3) Uani 1 1 d . . . O2 O 0.19384(11) 0.71591(9) 1.15379(5) 0.0531(2) Uani 1 1 d . . . O3 O 0.17131(12) 0.56762(11) 1.24547(5) 0.0644(3) Uani 1 1 d . . . O6 O 0.70087(11) 0.40931(10) 1.14626(6) 0.0588(3) Uani 1 1 d . . . C1 C 0.51264(13) 0.50233(11) 1.07343(7) 0.0399(3) Uani 1 1 d . . . O5 O 0.76683(11) 0.52417(12) 1.04295(7) 0.0692(3) Uani 1 1 d . . . C2 C 0.41249(14) 0.47585(12) 1.12692(7) 0.0428(3) Uani 1 1 d . . . H2 H 0.4423 0.4374 1.1729 0.051 Uiso 1 1 calc R . . C8 C 0.33347(14) 0.64421(13) 0.90896(7) 0.0442(3) Uani 1 1 d . . . H8B H 0.3655 0.7267 0.9286 0.053 Uiso 1 1 calc R . . H8A H 0.4069 0.6155 0.8720 0.053 Uiso 1 1 calc R . . C10 C 0.19287(14) 0.74331(11) 0.79391(6) 0.0417(3) Uani 1 1 d . . . C6 C 0.24441(16) 0.72276(12) 1.07343(7) 0.0464(3) Uani 1 1 d . . . H6B H 0.3465 0.7499 1.0710 0.056 Uiso 1 1 calc R . . H6A H 0.1847 0.7823 1.0438 0.056 Uiso 1 1 calc R . . C15 C 0.05835(15) 0.77695(13) 0.76111(8) 0.0506(3) Uani 1 1 d . . . H15 H -0.0288 0.7485 0.7835 0.061 Uiso 1 1 calc R . . C4 C 0.22709(13) 0.58683(11) 1.04266(7) 0.0400(3) Uani 1 1 d . . . H4 H 0.1252 0.5749 1.0254 0.048 Uiso 1 1 calc R . . C5 C 0.33094(13) 0.54932(12) 0.97666(6) 0.0408(3) Uani 1 1 d . . . C3 C 0.25241(14) 0.50606(12) 1.11556(7) 0.0425(3) Uani 1 1 d . . . H3 H 0.1932 0.4276 1.1143 0.051 Uiso 1 1 calc R . . C18 C 0.30029(19) 0.41325(13) 0.94998(8) 0.0567(3) Uani 1 1 d . . . H18B H 0.1978 0.4047 0.9373 0.085 Uiso 1 1 calc R . . H18C H 0.3249 0.3544 0.9907 0.085 Uiso 1 1 calc R . . H18A H 0.3588 0.3946 0.9051 0.085 Uiso 1 1 calc R . . C9 C 0.18971(14) 0.66336(12) 0.86602(6) 0.0425(3) Uani 1 1 d . . . C7 C 0.20123(14) 0.59467(13) 1.17968(7) 0.0471(3) Uani 1 1 d . . . C11 C 0.32155(17) 0.78458(14) 0.75909(8) 0.0528(3) Uani 1 1 d . . . H11 H 0.4121 0.7627 0.7805 0.063 Uiso 1 1 calc R . . C17 C 0.85290(17) 0.38639(16) 1.16407(10) 0.0650(4) Uani 1 1 d . . . H17A H 0.9024 0.3547 1.1188 0.097 Uiso 1 1 calc R . . H17B H 0.8598 0.3242 1.2049 0.097 Uiso 1 1 calc R . . H17C H 0.8982 0.4649 1.1804 0.097 Uiso 1 1 calc R . . C16 C 0.67361(14) 0.48065(12) 1.08424(7) 0.0431(3) Uani 1 1 d . . . C14 C 0.05355(19) 0.85217(16) 0.69557(9) 0.0641(4) Uani 1 1 d . . . H14 H -0.0369 0.8756 0.6746 0.077 Uiso 1 1 calc R . . C13 C 0.1818(2) 0.89287(16) 0.66099(9) 0.0699(4) Uani 1 1 d . . . H13 H 0.1781 0.9433 0.6166 0.084 Uiso 1 1 calc R . . C12 C 0.3161(2) 0.85862(16) 0.69227(9) 0.0667(4) Uani 1 1 d . . . H12 H 0.4029 0.8851 0.6686 0.080 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 0.0374(4) 0.0604(5) 0.0374(4) 0.0114(4) -0.0006(3) 0.0028(4) O4 0.0429(5) 0.0814(7) 0.0577(6) 0.0142(5) -0.0059(4) -0.0072(5) O2 0.0613(6) 0.0553(5) 0.0428(4) -0.0032(4) 0.0059(4) 0.0095(4) O3 0.0674(6) 0.0871(7) 0.0388(5) 0.0068(5) 0.0116(5) 0.0086(6) O6 0.0459(5) 0.0704(6) 0.0601(6) 0.0255(5) -0.0081(4) 0.0048(4) C1 0.0428(6) 0.0396(6) 0.0373(5) 0.0051(4) -0.0027(5) 0.0033(4) O5 0.0450(6) 0.0922(8) 0.0703(7) 0.0321(6) 0.0046(5) 0.0063(5) C2 0.0475(7) 0.0427(6) 0.0380(6) 0.0077(5) -0.0001(5) 0.0039(5) C8 0.0397(6) 0.0578(7) 0.0350(5) 0.0059(5) -0.0014(5) 0.0015(5) C10 0.0454(6) 0.0442(6) 0.0355(5) -0.0052(4) -0.0064(5) 0.0062(5) C6 0.0511(7) 0.0470(6) 0.0412(6) 0.0026(5) 0.0020(5) 0.0053(5) C15 0.0474(7) 0.0590(7) 0.0455(7) -0.0044(6) -0.0078(5) 0.0091(6) C4 0.0358(6) 0.0481(6) 0.0362(6) 0.0016(5) -0.0015(4) -0.0007(4) C5 0.0383(6) 0.0501(6) 0.0340(5) 0.0011(4) -0.0024(5) 0.0011(5) C3 0.0431(6) 0.0455(6) 0.0390(6) 0.0049(5) 0.0037(5) -0.0029(5) C18 0.0707(9) 0.0539(7) 0.0456(7) -0.0080(6) -0.0051(7) 0.0018(7) C9 0.0413(6) 0.0486(6) 0.0377(5) -0.0024(5) -0.0027(5) 0.0023(5) C7 0.0394(6) 0.0623(7) 0.0395(6) 0.0024(5) 0.0022(5) 0.0044(6) C11 0.0492(7) 0.0623(7) 0.0469(6) 0.0077(6) -0.0031(6) 0.0046(6) C17 0.0510(8) 0.0690(9) 0.0750(10) 0.0135(8) -0.0189(7) 0.0083(7) C16 0.0432(6) 0.0431(5) 0.0431(6) 0.0052(5) -0.0018(5) 0.0031(5) C14 0.0678(10) 0.0702(9) 0.0542(8) 0.0051(7) -0.0188(7) 0.0170(8) C13 0.0901(12) 0.0690(9) 0.0506(7) 0.0160(7) -0.0113(8) 0.0097(9) C12 0.0692(10) 0.0750(10) 0.0561(8) 0.0180(7) 0.0045(8) 0.0017(8) _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 1.3632(14) . ? O1 C5 1.4665(14) . ? O4 C9 1.2077(16) . ? O2 C7 1.3440(16) . ? O2 C6 1.4633(15) . ? O3 C7 1.2017(15) . ? O6 C16 1.3277(15) . ? O6 C17 1.4344(17) . ? C1 C2 1.3253(17) . ? C1 C16 1.4907(18) . ? O5 C16 1.1964(16) . ? C2 C3 1.5002(18) . ? C2 H2 0.9300 . ? C8 C9 1.5144(17) . ? C8 C5 1.5325(16) . ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C10 C11 1.383(2) . ? C10 C15 1.3913(18) . ? C10 C9 1.4993(16) . ? C6 C4 1.5234(17) . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? C15 C14 1.378(2) . ? C15 H15 0.9300 . ? C4 C5 1.5301(16) . ? C4 C3 1.5324(16) . ? C4 H4 0.9800 . ? C5 C18 1.5192(18) . ? C3 C7 1.5157(17) . ? C3 H3 0.9800 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C18 H18A 0.9600 . ? C11 C12 1.390(2) . ? C11 H11 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C14 C13 1.376(3) . ? C14 H14 0.9300 . ? C13 C12 1.380(2) . ? C13 H13 0.9300 . ? C12 H12 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 C1 O1 C5 115.89(9) . . ? C7 O2 C6 110.22(10) . . ? C16 O6 C17 116.48(11) . . ? C2 C1 O1 125.20(11) . . ? C2 C1 C16 123.63(11) . . ? O1 C1 C16 111.13(10) . . ? C1 C2 C3 122.00(10) . . ? C1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C9 C8 C5 116.47(10) . . ? C9 C8 H8B 108.2 . . ? C5 C8 H8B 108.2 . . ? C9 C8 H8A 108.2 . . ? C5 C8 H8A 108.2 . . ? H8B C8 H8A 107.3 . . ? C11 C10 C15 119.09(11) . . ? C11 C10 C9 123.41(11) . . ? C15 C10 C9 117.50(12) . . ? O2 C6 C4 104.64(10) . . ? O2 C6 H6B 110.8 . . ? C4 C6 H6B 110.8 . . ? O2 C6 H6A 110.8 . . ? C4 C6 H6A 110.8 . . ? H6B C6 H6A 108.9 . . ? C14 C15 C10 120.38(14) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C6 C4 C5 115.75(10) . . ? C6 C4 C3 102.17(9) . . ? C5 C4 C3 112.23(9) . . ? C6 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? O1 C5 C18 108.42(10) . . ? O1 C5 C4 109.83(9) . . ? C18 C5 C4 110.63(11) . . ? O1 C5 C8 101.00(9) . . ? C18 C5 C8 112.08(10) . . ? C4 C5 C8 114.32(10) . . ? C2 C3 C7 109.27(11) . . ? C2 C3 C4 111.62(9) . . ? C7 C3 C4 102.59(10) . . ? C2 C3 H3 111.0 . . ? C7 C3 H3 111.0 . . ? C4 C3 H3 111.0 . . ? C5 C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C5 C18 H18A 109.5 . . ? H18B C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? O4 C9 C10 120.38(11) . . ? O4 C9 C8 121.97(11) . . ? C10 C9 C8 117.62(11) . . ? O3 C7 O2 121.63(13) . . ? O3 C7 C3 128.05(13) . . ? O2 C7 C3 110.32(10) . . ? C10 C11 C12 120.26(14) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C16 O6 124.18(12) . . ? O5 C16 C1 124.15(11) . . ? O6 C16 C1 111.65(10) . . ? C13 C14 C15 120.36(13) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C13 C12 119.84(13) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C12 C11 120.04(15) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C1 C2 -18.79(17) . . . . ? C5 O1 C1 C16 163.38(10) . . . . ? O1 C1 C2 C3 -1.15(19) . . . . ? C16 C1 C2 C3 176.42(12) . . . . ? C7 O2 C6 C4 21.70(14) . . . . ? C11 C10 C15 C14 -1.08(19) . . . . ? C9 C10 C15 C14 178.86(12) . . . . ? O2 C6 C4 C5 -153.12(10) . . . . ? O2 C6 C4 C3 -30.86(12) . . . . ? C1 O1 C5 C18 -75.00(12) . . . . ? C1 O1 C5 C4 45.99(13) . . . . ? C1 O1 C5 C8 167.07(9) . . . . ? C6 C4 C5 O1 61.71(13) . . . . ? C3 C4 C5 O1 -55.03(13) . . . . ? C6 C4 C5 C18 -178.64(11) . . . . ? C3 C4 C5 C18 64.62(13) . . . . ? C6 C4 C5 C8 -50.98(14) . . . . ? C3 C4 C5 C8 -167.72(10) . . . . ? C9 C8 C5 O1 -179.76(10) . . . . ? C9 C8 C5 C18 65.01(15) . . . . ? C9 C8 C5 C4 -61.91(14) . . . . ? C1 C2 C3 C7 -121.40(13) . . . . ? C1 C2 C3 C4 -8.64(17) . . . . ? C6 C4 C3 C2 -88.27(12) . . . . ? C5 C4 C3 C2 36.36(14) . . . . ? C6 C4 C3 C7 28.61(12) . . . . ? C5 C4 C3 C7 153.24(10) . . . . ? C11 C10 C9 O4 -172.54(13) . . . . ? C15 C10 C9 O4 7.52(18) . . . . ? C11 C10 C9 C8 9.44(17) . . . . ? C15 C10 C9 C8 -170.50(11) . . . . ? C5 C8 C9 O4 9.14(18) . . . . ? C5 C8 C9 C10 -172.87(10) . . . . ? C6 O2 C7 O3 176.57(13) . . . . ? C6 O2 C7 C3 -2.70(14) . . . . ? C2 C3 C7 O3 -77.79(17) . . . . ? C4 C3 C7 O3 163.66(14) . . . . ? C2 C3 C7 O2 101.42(12) . . . . ? C4 C3 C7 O2 -17.13(13) . . . . ? C15 C10 C11 C12 0.0(2) . . . . ? C9 C10 C11 C12 -179.95(13) . . . . ? C17 O6 C16 O5 1.0(2) . . . . ? C17 O6 C16 C1 -177.65(13) . . . . ? C2 C1 C16 O5 -166.20(14) . . . . ? O1 C1 C16 O5 11.67(18) . . . . ? C2 C1 C16 O6 12.51(18) . . . . ? O1 C1 C16 O6 -169.63(10) . . . . ? C10 C15 C14 C13 1.2(2) . . . . ? C15 C14 C13 C12 -0.3(3) . . . . ? C14 C13 C12 C11 -0.8(3) . . . . ? C10 C11 C12 C13 1.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 71.96 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.164 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 915445'