# Electronic Supplementary Material (ESI) for Chemical Communications # 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_b _database_code_depnum_ccdc_archive 'CCDC 807572' #TrackingRef '20110111.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 O4' _chemical_formula_weight 306.30 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 7.2210(14) _cell_length_b 17.001(3) _cell_length_c 23.199(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2848.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9900 _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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 5158 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.42 _reflns_number_total 2623 _reflns_number_gt 1722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2623 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 -0.0656(2) 0.78747(9) 0.24337(7) 0.0496(4) Uani 1 1 d . . . C1 C 0.0142(3) 0.74748(12) 0.35938(10) 0.0465(6) Uani 1 1 d . . . H1A H -0.0429 0.7957 0.3527 0.056 Uiso 1 1 calc R . . O2 O 0.07343(19) 0.68236(7) 0.20872(6) 0.0376(4) Uani 1 1 d . . . C2 C 0.0518(4) 0.72435(14) 0.41474(10) 0.0525(7) Uani 1 1 d . . . H2A H 0.0204 0.7567 0.4456 0.063 Uiso 1 1 calc R . . O3 O 0.3694(3) 0.37566(9) 0.06877(6) 0.0560(5) Uani 1 1 d . . . C3 C 0.1368(4) 0.65252(14) 0.42455(10) 0.0512(6) Uani 1 1 d . . . H3A H 0.1623 0.6367 0.4621 0.061 Uiso 1 1 calc R . . O4 O 0.2447(3) 0.50108(9) 0.02093(6) 0.0558(5) Uani 1 1 d . . . C4 C 0.1838(3) 0.60451(13) 0.37932(9) 0.0433(6) Uani 1 1 d . . . H4A H 0.2419 0.5568 0.3868 0.052 Uiso 1 1 calc R . . C5 C 0.1461(3) 0.62587(11) 0.32218(8) 0.0336(5) Uani 1 1 d . . . C6 C 0.0608(3) 0.69958(12) 0.31307(9) 0.0351(5) Uani 1 1 d . . . C7 C 0.1879(3) 0.58018(11) 0.27166(9) 0.0333(5) Uani 1 1 d . . . C8 C 0.1502(3) 0.61051(11) 0.21904(9) 0.0326(5) Uani 1 1 d . . . C9 C 0.0162(3) 0.72789(11) 0.25493(10) 0.0374(5) Uani 1 1 d . . . C10 C 0.2641(3) 0.50054(11) 0.26238(8) 0.0334(5) Uani 1 1 d . . . C11 C 0.2686(3) 0.49061(11) 0.19877(9) 0.0344(5) Uani 1 1 d . . . C12 C 0.1997(3) 0.55808(11) 0.17261(8) 0.0340(5) Uani 1 1 d . . . C13 C 0.3281(3) 0.42779(12) 0.16534(9) 0.0384(5) Uani 1 1 d . . . H13A H 0.3747 0.3826 0.1826 0.046 Uiso 1 1 calc R . . C14 C 0.3170(3) 0.43349(13) 0.10609(9) 0.0406(5) Uani 1 1 d . . . C15 C 0.2461(3) 0.50235(13) 0.07989(9) 0.0401(5) Uani 1 1 d . . . C16 C 0.1866(3) 0.56480(12) 0.11295(8) 0.0375(5) Uani 1 1 d . . . H16A H 0.1393 0.6101 0.0959 0.045 Uiso 1 1 calc R . . C17 C 0.3165(3) 0.44596(13) 0.29966(9) 0.0461(6) Uani 1 1 d . . . H17A H 0.3076 0.4555 0.3390 0.055 Uiso 1 1 calc R . . H17B H 0.3622 0.3981 0.2865 0.055 Uiso 1 1 calc R . . C18 C 0.4620(4) 0.30925(14) 0.09209(10) 0.0591(7) Uani 1 1 d . . . H18A H 0.4913 0.2731 0.0617 0.089 Uiso 1 1 calc R . . H18B H 0.3831 0.2838 0.1197 0.089 Uiso 1 1 calc R . . H18C H 0.5741 0.3259 0.1107 0.089 Uiso 1 1 calc R . . C19 C 0.1954(4) 0.57183(15) -0.00750(10) 0.0656(8) Uani 1 1 d . . . H19A H 0.1994 0.5639 -0.0485 0.098 Uiso 1 1 calc R . . H19B H 0.2809 0.6126 0.0030 0.098 Uiso 1 1 calc R . . H19C H 0.0724 0.5869 0.0037 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 O1 0.0536(10) 0.0353(8) 0.0598(11) 0.0032(8) -0.0018(8) 0.0076(8) C1 0.0483(14) 0.0390(12) 0.0521(15) -0.0038(11) 0.0094(12) -0.0027(11) O2 0.0408(9) 0.0329(8) 0.0391(9) 0.0033(6) -0.0015(7) 0.0017(7) C2 0.0608(17) 0.0542(15) 0.0425(14) -0.0087(12) 0.0070(12) -0.0029(13) O3 0.0790(13) 0.0489(10) 0.0401(9) -0.0051(8) 0.0020(9) 0.0155(9) C3 0.0568(16) 0.0569(15) 0.0399(14) -0.0009(12) 0.0016(12) -0.0011(13) O4 0.0773(12) 0.0559(10) 0.0341(9) 0.0029(8) -0.0003(8) 0.0055(9) C4 0.0453(14) 0.0442(13) 0.0404(13) 0.0008(11) -0.0005(11) 0.0042(11) C5 0.0283(11) 0.0367(11) 0.0359(12) 0.0018(9) 0.0012(9) -0.0048(9) C6 0.0300(11) 0.0332(11) 0.0422(12) 0.0001(10) 0.0031(10) -0.0053(9) C7 0.0296(11) 0.0332(11) 0.0370(12) 0.0016(9) -0.0013(10) -0.0039(9) C8 0.0287(11) 0.0298(11) 0.0394(12) 0.0037(9) -0.0040(9) -0.0023(9) C9 0.0345(12) 0.0304(11) 0.0472(13) -0.0007(10) 0.0023(10) -0.0057(10) C10 0.0283(11) 0.0344(11) 0.0374(13) 0.0002(9) -0.0006(10) -0.0038(9) C11 0.0300(12) 0.0351(11) 0.0383(12) 0.0000(10) 0.0007(10) -0.0048(9) C12 0.0311(12) 0.0360(11) 0.0350(12) 0.0016(10) -0.0007(9) -0.0033(10) C13 0.0388(13) 0.0353(11) 0.0412(13) 0.0032(10) 0.0000(10) 0.0006(10) C14 0.0416(13) 0.0410(12) 0.0392(12) -0.0041(10) 0.0038(11) -0.0015(10) C15 0.0403(13) 0.0480(13) 0.0321(12) -0.0003(10) -0.0011(10) -0.0043(11) C16 0.0353(12) 0.0381(12) 0.0392(13) 0.0053(10) -0.0031(10) -0.0016(10) C17 0.0590(16) 0.0404(13) 0.0389(12) 0.0015(11) -0.0015(12) 0.0056(12) C18 0.0732(19) 0.0483(15) 0.0556(16) -0.0018(12) 0.0079(14) 0.0153(14) C19 0.094(2) 0.0640(18) 0.0386(14) 0.0116(12) -0.0036(15) -0.0044(15) _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 C9 1.203(2) . ? C1 C2 1.370(3) . ? C1 C6 1.389(3) . ? C1 H1A 0.9300 . ? O2 C8 1.363(2) . ? O2 C9 1.385(2) . ? C2 C3 1.386(3) . ? C2 H2A 0.9300 . ? O3 C14 1.364(2) . ? O3 C18 1.419(3) . ? C3 C4 1.372(3) . ? C3 H3A 0.9300 . ? O4 C15 1.368(2) . ? O4 C19 1.417(3) . ? C4 C5 1.401(3) . ? C4 H4A 0.9300 . ? C5 C6 1.412(3) . ? C5 C7 1.438(3) . ? C6 C9 1.468(3) . ? C7 C8 1.353(3) . ? C7 C10 1.477(3) . ? C8 C12 1.443(3) . ? C10 C17 1.324(3) . ? C10 C11 1.486(3) . ? C11 C13 1.388(3) . ? C11 C12 1.390(3) . ? C12 C16 1.392(3) . ? C13 C14 1.380(3) . ? C13 H13A 0.9300 . ? C14 C15 1.415(3) . ? C15 C16 1.378(3) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C17 H17B 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C2 C1 C6 120.6(2) . . ? C2 C1 H1A 119.7 . . ? C6 C1 H1A 119.7 . . ? C8 O2 C9 119.10(16) . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C14 O3 C18 117.53(17) . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C15 O4 C19 116.98(17) . . ? C3 C4 C5 121.4(2) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C4 C5 C6 117.16(19) . . ? C4 C5 C7 126.17(19) . . ? C6 C5 C7 116.67(18) . . ? C1 C6 C5 120.7(2) . . ? C1 C6 C9 117.73(19) . . ? C5 C6 C9 121.62(19) . . ? C8 C7 C5 119.16(18) . . ? C8 C7 C10 107.02(17) . . ? C5 C7 C10 133.79(18) . . ? C7 C8 O2 125.60(18) . . ? C7 C8 C12 112.84(17) . . ? O2 C8 C12 121.56(18) . . ? O1 C9 O2 116.39(19) . . ? O1 C9 C6 126.1(2) . . ? O2 C9 C6 117.54(18) . . ? C17 C10 C7 130.8(2) . . ? C17 C10 C11 124.26(19) . . ? C7 C10 C11 104.90(17) . . ? C13 C11 C12 120.12(19) . . ? C13 C11 C10 130.49(19) . . ? C12 C11 C10 109.39(17) . . ? C11 C12 C16 121.74(18) . . ? C11 C12 C8 105.82(17) . . ? C16 C12 C8 132.43(19) . . ? C14 C13 C11 118.98(19) . . ? C14 C13 H13A 120.5 . . ? C11 C13 H13A 120.5 . . ? O3 C14 C13 124.44(19) . . ? O3 C14 C15 115.10(18) . . ? C13 C14 C15 120.46(19) . . ? O4 C15 C16 124.49(19) . . ? O4 C15 C14 114.77(18) . . ? C16 C15 C14 120.74(18) . . ? C15 C16 C12 117.96(19) . . ? C15 C16 H16A 121.0 . . ? C12 C16 H16A 121.0 . . ? C10 C17 H17A 120.0 . . ? C10 C17 H17B 120.0 . . ? H17A C17 H17B 120.0 . . ? 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 . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C6 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C3 C4 C5 C7 -179.6(2) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? C2 C1 C6 C9 179.9(2) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C7 C5 C6 C1 179.56(19) . . . . ? C4 C5 C6 C9 179.65(19) . . . . ? C7 C5 C6 C9 0.3(3) . . . . ? C4 C5 C7 C8 -177.1(2) . . . . ? C6 C5 C7 C8 2.2(3) . . . . ? C4 C5 C7 C10 5.0(4) . . . . ? C6 C5 C7 C10 -175.7(2) . . . . ? C5 C7 C8 O2 -0.2(3) . . . . ? C10 C7 C8 O2 178.24(18) . . . . ? C5 C7 C8 C12 179.94(18) . . . . ? C10 C7 C8 C12 -1.6(2) . . . . ? C9 O2 C8 C7 -4.5(3) . . . . ? C9 O2 C8 C12 175.33(18) . . . . ? C8 O2 C9 O1 -173.52(18) . . . . ? C8 O2 C9 C6 6.7(3) . . . . ? C1 C6 C9 O1 -3.8(3) . . . . ? C5 C6 C9 O1 175.5(2) . . . . ? C1 C6 C9 O2 175.95(18) . . . . ? C5 C6 C9 O2 -4.8(3) . . . . ? C8 C7 C10 C17 -177.5(2) . . . . ? C5 C7 C10 C17 0.6(4) . . . . ? C8 C7 C10 C11 1.3(2) . . . . ? C5 C7 C10 C11 179.4(2) . . . . ? C17 C10 C11 C13 -1.7(4) . . . . ? C7 C10 C11 C13 179.5(2) . . . . ? C17 C10 C11 C12 178.4(2) . . . . ? C7 C10 C11 C12 -0.5(2) . . . . ? C13 C11 C12 C16 0.5(3) . . . . ? C10 C11 C12 C16 -179.53(19) . . . . ? C13 C11 C12 C8 179.61(19) . . . . ? C10 C11 C12 C8 -0.4(2) . . . . ? C7 C8 C12 C11 1.3(2) . . . . ? O2 C8 C12 C11 -178.56(18) . . . . ? C7 C8 C12 C16 -179.7(2) . . . . ? O2 C8 C12 C16 0.4(3) . . . . ? C12 C11 C13 C14 -0.2(3) . . . . ? C10 C11 C13 C14 179.8(2) . . . . ? C18 O3 C14 C13 -8.0(3) . . . . ? C18 O3 C14 C15 172.6(2) . . . . ? C11 C13 C14 O3 -179.4(2) . . . . ? C11 C13 C14 C15 0.0(3) . . . . ? C19 O4 C15 C16 6.3(3) . . . . ? C19 O4 C15 C14 -172.9(2) . . . . ? O3 C14 C15 O4 -1.4(3) . . . . ? C13 C14 C15 O4 179.1(2) . . . . ? O3 C14 C15 C16 179.4(2) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? O4 C15 C16 C12 -178.8(2) . . . . ? C14 C15 C16 C12 0.4(3) . . . . ? C11 C12 C16 C15 -0.6(3) . . . . ? C8 C12 C16 C15 -179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.043 # Attachment 'MolecularStructureName.pdf' data_b _database_code_depnum_ccdc_archive 'CCDC 843665' #TrackingRef '20110909.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 O4' _chemical_formula_weight 332.34 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 8.0400(16) _cell_length_b 10.112(2) _cell_length_c 11.172(2) _cell_angle_alpha 70.69(3) _cell_angle_beta 82.57(3) _cell_angle_gamma 76.65(3) _cell_volume 832.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9730 _exptl_absorpt_correction_T_max 0.9909 _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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 3294 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.39 _reflns_number_total 3059 _reflns_number_gt 2039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.1000P)^2^+0.2000P] 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 0.056(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3059 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.3682(2) 0.39129(17) 0.92798(15) 0.0453(5) Uani 1 1 d . . . C1 C 0.1790(3) 0.4169(3) 1.1107(2) 0.0419(6) Uani 1 1 d . . . O2 O 0.5365(3) 0.3735(2) 0.75928(19) 0.0681(6) Uani 1 1 d . . . C2 C 0.1736(3) 0.2768(3) 1.1827(2) 0.0463(6) Uani 1 1 d . . . H2A H 0.2345 0.2007 1.1557 0.056 Uiso 1 1 calc R . . O3 O 0.0582(3) 0.1223(2) 1.37576(18) 0.0635(6) Uani 1 1 d . . . C3 C 0.0755(3) 0.2535(3) 1.2953(2) 0.0490(7) Uani 1 1 d . . . O4 O -0.1108(3) 0.3324(2) 1.44742(18) 0.0752(7) Uani 1 1 d . . . C4 C -0.0198(3) 0.3700(3) 1.3342(2) 0.0532(7) Uani 1 1 d . . . C5 C -0.0123(3) 0.5095(3) 1.2613(2) 0.0530(7) Uani 1 1 d . . . H5A H -0.0732 0.5861 1.2877 0.064 Uiso 1 1 calc R . . C6 C 0.0879(3) 0.5327(3) 1.1481(2) 0.0449(6) Uani 1 1 d . . . C7 C 0.1235(3) 0.6671(3) 1.0523(2) 0.0477(7) Uani 1 1 d . . . C8 C 0.2475(3) 0.6201(3) 0.9566(2) 0.0426(6) Uani 1 1 d . . . C9 C 0.2700(3) 0.4755(3) 0.9927(2) 0.0408(6) Uani 1 1 d . . . C10 C 0.3372(3) 0.6904(3) 0.8427(2) 0.0428(6) Uani 1 1 d . . . C11 C 0.4347(3) 0.6064(3) 0.7758(2) 0.0467(7) Uani 1 1 d . . . H11A H 0.4925 0.6508 0.7009 0.056 Uiso 1 1 calc R . . C12 C 0.4538(3) 0.4545(3) 0.8133(2) 0.0466(7) Uani 1 1 d . . . C13 C 0.0472(4) 0.7974(3) 1.0531(3) 0.0698(9) Uani 1 1 d . . . H13A H 0.0692 0.8764 0.9861 0.084 Uiso 1 1 calc R . . H13B H -0.0285 0.8101 1.1206 0.084 Uiso 1 1 calc R . . C14 C 0.3388(3) 0.8459(3) 0.7972(2) 0.0474(7) Uani 1 1 d . . . C15 C 0.3128(4) 0.9239(3) 0.6717(3) 0.0604(8) Uani 1 1 d . . . H15A H 0.2864 0.8808 0.6168 0.073 Uiso 1 1 calc R . . C16 C 0.3260(5) 1.0659(4) 0.6273(3) 0.0736(10) Uani 1 1 d . . . H16A H 0.3070 1.1182 0.5427 0.088 Uiso 1 1 calc R . . C17 C 0.3665(4) 1.1299(3) 0.7058(4) 0.0714(9) Uani 1 1 d . . . H17A H 0.3756 1.2256 0.6748 0.086 Uiso 1 1 calc R . . C18 C 0.3941(4) 1.0537(3) 0.8311(3) 0.0649(8) Uani 1 1 d . . . H18A H 0.4235 1.0973 0.8845 0.078 Uiso 1 1 calc R . . C19 C 0.3782(4) 0.9120(3) 0.8777(3) 0.0560(7) Uani 1 1 d . . . H19A H 0.3939 0.8611 0.9629 0.067 Uiso 1 1 calc R . . C20 C 0.1424(5) 0.0021(3) 1.3374(3) 0.0766(10) Uani 1 1 d . . . H20A H 0.1209 -0.0838 1.4013 0.115 Uiso 1 1 calc R . . H20B H 0.2634 -0.0003 1.3263 0.115 Uiso 1 1 calc R . . H20C H 0.1000 0.0091 1.2586 0.115 Uiso 1 1 calc R . . C21 C -0.2233(4) 0.4417(4) 1.4890(3) 0.0770(10) Uani 1 1 d . . . H21A H -0.2782 0.3995 1.5698 0.116 Uiso 1 1 calc R . . H21B H -0.3085 0.4923 1.4281 0.116 Uiso 1 1 calc R . . H21C H -0.1591 0.5072 1.4971 0.116 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 0.0481(10) 0.0472(10) 0.0399(10) -0.0147(8) 0.0104(8) -0.0137(8) C1 0.0361(13) 0.0538(15) 0.0364(13) -0.0141(12) 0.0019(10) -0.0121(11) O2 0.0818(15) 0.0636(13) 0.0623(13) -0.0318(11) 0.0308(11) -0.0226(11) C2 0.0423(14) 0.0523(16) 0.0417(14) -0.0124(12) 0.0035(11) -0.0113(12) O3 0.0658(13) 0.0628(13) 0.0465(11) -0.0015(10) 0.0137(10) -0.0152(10) C3 0.0431(15) 0.0612(18) 0.0351(13) -0.0062(13) 0.0026(11) -0.0116(13) O4 0.0757(15) 0.0855(16) 0.0443(12) -0.0103(11) 0.0245(10) -0.0069(12) C4 0.0463(16) 0.0744(19) 0.0312(13) -0.0096(13) 0.0062(11) -0.0121(14) C5 0.0494(16) 0.0628(18) 0.0441(15) -0.0205(14) 0.0054(12) -0.0050(13) C6 0.0398(14) 0.0562(16) 0.0377(13) -0.0155(12) 0.0019(11) -0.0086(12) C7 0.0469(15) 0.0520(16) 0.0437(15) -0.0167(12) 0.0026(12) -0.0096(12) C8 0.0386(14) 0.0505(15) 0.0387(13) -0.0150(11) 0.0016(11) -0.0097(11) C9 0.0371(13) 0.0469(15) 0.0381(13) -0.0142(11) 0.0030(11) -0.0097(11) C10 0.0427(14) 0.0472(15) 0.0402(13) -0.0135(11) -0.0020(11) -0.0125(11) C11 0.0488(15) 0.0541(16) 0.0377(13) -0.0134(12) 0.0102(11) -0.0193(13) C12 0.0481(15) 0.0549(16) 0.0392(14) -0.0178(12) 0.0118(12) -0.0179(13) C13 0.070(2) 0.060(2) 0.071(2) -0.0237(16) 0.0213(17) -0.0049(16) C14 0.0430(15) 0.0446(15) 0.0517(16) -0.0110(12) 0.0010(12) -0.0110(12) C15 0.068(2) 0.0597(18) 0.0522(17) -0.0084(14) -0.0036(15) -0.0240(15) C16 0.083(2) 0.062(2) 0.066(2) 0.0009(16) -0.0067(18) -0.0235(18) C17 0.063(2) 0.0446(17) 0.099(3) -0.0130(17) -0.0012(19) -0.0122(15) C18 0.0634(19) 0.0536(18) 0.082(2) -0.0278(16) -0.0072(17) -0.0086(15) C19 0.0586(18) 0.0494(16) 0.0604(18) -0.0194(14) -0.0040(14) -0.0083(13) C20 0.081(2) 0.059(2) 0.067(2) -0.0023(16) 0.0188(18) -0.0103(17) C21 0.064(2) 0.113(3) 0.0489(17) -0.0304(18) 0.0198(15) -0.0117(19) _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 C9 1.349(3) . ? O1 C12 1.399(3) . ? C1 C2 1.387(3) . ? C1 C6 1.389(4) . ? C1 C9 1.435(3) . ? O2 C12 1.204(3) . ? C2 C3 1.376(4) . ? C2 H2A 0.9300 . ? O3 C3 1.361(3) . ? O3 C20 1.417(4) . ? C3 C4 1.413(4) . ? O4 C4 1.361(3) . ? O4 C21 1.423(4) . ? C4 C5 1.387(4) . ? C5 C6 1.390(4) . ? C5 H5A 0.9300 . ? C6 C7 1.488(4) . ? C7 C13 1.321(4) . ? C7 C8 1.484(3) . ? C8 C9 1.356(3) . ? C8 C10 1.431(3) . ? C10 C11 1.362(3) . ? C10 C14 1.487(3) . ? C11 C12 1.428(4) . ? C11 H11A 0.9300 . ? C13 H13A 0.9300 . ? C13 H13B 0.9300 . ? C14 C15 1.379(4) . ? C14 C19 1.387(4) . ? C15 C16 1.380(4) . ? C15 H15A 0.9300 . ? C16 C17 1.357(5) . ? C16 H16A 0.9300 . ? C17 C18 1.375(5) . ? C17 H17A 0.9300 . ? C18 C19 1.383(4) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C9 O1 C12 119.11(19) . . ? C2 C1 C6 122.1(2) . . ? C2 C1 C9 131.5(2) . . ? C6 C1 C9 106.3(2) . . ? C3 C2 C1 118.1(3) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C3 O3 C20 117.1(2) . . ? O3 C3 C2 124.7(3) . . ? O3 C3 C4 114.8(2) . . ? C2 C3 C4 120.5(2) . . ? C4 O4 C21 118.8(2) . . ? O4 C4 C5 124.7(3) . . ? O4 C4 C3 114.7(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 118.7(3) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C1 C6 C5 119.8(2) . . ? C1 C6 C7 108.9(2) . . ? C5 C6 C7 131.2(2) . . ? C13 C7 C8 129.9(3) . . ? C13 C7 C6 124.8(3) . . ? C8 C7 C6 105.1(2) . . ? C9 C8 C10 118.2(2) . . ? C9 C8 C7 106.4(2) . . ? C10 C8 C7 135.3(2) . . ? O1 C9 C8 125.2(2) . . ? O1 C9 C1 121.7(2) . . ? C8 C9 C1 113.1(2) . . ? C11 C10 C8 116.9(2) . . ? C11 C10 C14 118.4(2) . . ? C8 C10 C14 124.6(2) . . ? C10 C11 C12 124.2(2) . . ? C10 C11 H11A 117.9 . . ? C12 C11 H11A 117.9 . . ? O2 C12 O1 115.7(2) . . ? O2 C12 C11 128.0(2) . . ? O1 C12 C11 116.3(2) . . ? C7 C13 H13A 120.0 . . ? C7 C13 H13B 120.0 . . ? H13A C13 H13B 120.0 . . ? C15 C14 C19 119.2(3) . . ? C15 C14 C10 120.0(2) . . ? C19 C14 C10 120.6(2) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C14 120.0(3) . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(4) . . . . ? C9 C1 C2 C3 178.6(2) . . . . ? C20 O3 C3 C2 -2.6(4) . . . . ? C20 O3 C3 C4 176.1(3) . . . . ? C1 C2 C3 O3 -179.9(2) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C21 O4 C4 C5 8.0(4) . . . . ? C21 O4 C4 C3 -174.2(3) . . . . ? O3 C3 C4 O4 1.5(4) . . . . ? C2 C3 C4 O4 -179.8(2) . . . . ? O3 C3 C4 C5 179.4(2) . . . . ? C2 C3 C4 C5 -1.9(4) . . . . ? O4 C4 C5 C6 179.0(3) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C9 C1 C6 C5 -179.2(2) . . . . ? C2 C1 C6 C7 178.9(2) . . . . ? C9 C1 C6 C7 -0.5(3) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C4 C5 C6 C7 -178.9(3) . . . . ? C1 C6 C7 C13 174.3(3) . . . . ? C5 C6 C7 C13 -7.2(5) . . . . ? C1 C6 C7 C8 -1.5(3) . . . . ? C5 C6 C7 C8 177.0(3) . . . . ? C13 C7 C8 C9 -172.5(3) . . . . ? C6 C7 C8 C9 3.0(3) . . . . ? C13 C7 C8 C10 5.9(5) . . . . ? C6 C7 C8 C10 -178.6(3) . . . . ? C12 O1 C9 C8 -0.9(4) . . . . ? C12 O1 C9 C1 179.9(2) . . . . ? C10 C8 C9 O1 -1.5(4) . . . . ? C7 C8 C9 O1 177.2(2) . . . . ? C10 C8 C9 C1 177.7(2) . . . . ? C7 C8 C9 C1 -3.6(3) . . . . ? C2 C1 C9 O1 2.6(4) . . . . ? C6 C1 C9 O1 -178.1(2) . . . . ? C2 C1 C9 C8 -176.7(3) . . . . ? C6 C1 C9 C8 2.7(3) . . . . ? C9 C8 C10 C11 2.3(3) . . . . ? C7 C8 C10 C11 -175.9(3) . . . . ? C9 C8 C10 C14 -174.0(2) . . . . ? C7 C8 C10 C14 7.7(5) . . . . ? C8 C10 C11 C12 -0.9(4) . . . . ? C14 C10 C11 C12 175.7(2) . . . . ? C9 O1 C12 O2 -178.6(2) . . . . ? C9 O1 C12 C11 2.3(3) . . . . ? C10 C11 C12 O2 179.7(3) . . . . ? C10 C11 C12 O1 -1.4(4) . . . . ? C11 C10 C14 C15 49.8(4) . . . . ? C8 C10 C14 C15 -133.8(3) . . . . ? C11 C10 C14 C19 -125.6(3) . . . . ? C8 C10 C14 C19 50.7(4) . . . . ? C19 C14 C15 C16 0.0(5) . . . . ? C10 C14 C15 C16 -175.5(3) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C16 C17 C18 C19 -0.9(5) . . . . ? C17 C18 C19 C14 1.7(5) . . . . ? C15 C14 C19 C18 -1.2(4) . . . . ? C10 C14 C19 C18 174.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.263 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.061 # Attachment 'Structure and Name.pdf'