# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'David Spring' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email DRSPRING@CH.CAM.AC.UK _publ_section_title ; Copper Catalyzed Oxidation of Organozinc Halides ; loop_ _publ_author_name 'David Spring' 'David T. Blackwell' 'David J. Fox' 'Xianbin Su.' 'Kiyotaka Tanaka' # Attachment 'compound 2q.cif' data_ds0502 _database_code_depnum_ccdc_archive 'CCDC 609161' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 Cl2 O2' _chemical_formula_sum 'C30 H24 Cl2 O2' _chemical_formula_weight 487.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9644(3) _cell_length_b 10.6247(4) _cell_length_c 12.3651(5) _cell_angle_alpha 72.322(2) _cell_angle_beta 77.493(2) _cell_angle_gamma 86.707(2) _cell_volume 1217.61(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19638 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; No unusual features ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15013 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5487 _reflns_number_gt 4223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0289P)^2^+1.1592P] 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 5487 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 Cl1 Cl 1.15755(6) 0.70511(6) -0.10854(5) 0.03628(16) Uani 1 1 d . . . O1 O 0.64810(15) 0.56739(16) 0.35792(14) 0.0274(4) Uani 1 1 d . . . C1 C 1.0425(2) 0.6412(2) 0.02254(19) 0.0261(5) Uani 1 1 d . . . C2 C 0.9063(2) 0.6790(2) 0.0319(2) 0.0292(5) Uani 1 1 d . . . H2 H 0.8751 0.7344 -0.0339 0.035 Uiso 1 1 calc R . . C3 C 1.0880(2) 0.5545(2) 0.11594(19) 0.0264(5) Uani 1 1 d . . . H3 H 1.1812 0.5274 0.1084 0.032 Uiso 1 1 calc R . . C4 C 0.8161(2) 0.6357(2) 0.1375(2) 0.0269(5) Uani 1 1 d . . . H4 H 0.7234 0.6642 0.1448 0.032 Uiso 1 1 calc R . . C5 C 0.9952(2) 0.5080(2) 0.22055(19) 0.0234(5) Uani 1 1 d . . . H5 H 1.0246 0.4462 0.2843 0.028 Uiso 1 1 calc R . . C6 C 0.8592(2) 0.5505(2) 0.23371(18) 0.0206(4) Uani 1 1 d . . . C7 C 0.7587(2) 0.5109(2) 0.34694(18) 0.0204(4) Uani 1 1 d . . . C8 C 0.7923(2) 0.3980(2) 0.44751(18) 0.0195(4) Uani 1 1 d . . . H8 H 0.8923 0.4046 0.4464 0.023 Uiso 1 1 calc R . . C9 C 0.7682(2) 0.2669(2) 0.42834(17) 0.0200(4) Uani 1 1 d . . . C10 C 0.6429(2) 0.2354(2) 0.4103(2) 0.0267(5) Uani 1 1 d . . . H10 H 0.5689 0.2957 0.4123 0.032 Uiso 1 1 calc R . . C11 C 0.8729(2) 0.1752(2) 0.4259(2) 0.0270(5) Uani 1 1 d . . . H11 H 0.9591 0.1938 0.4391 0.032 Uiso 1 1 calc R . . C12 C 0.6247(2) 0.1170(2) 0.3895(2) 0.0302(5) Uani 1 1 d . . . H12 H 0.5380 0.0974 0.3779 0.036 Uiso 1 1 calc R . . C13 C 0.8545(2) 0.0569(2) 0.4046(2) 0.0314(5) Uani 1 1 d . . . H13 H 0.9282 -0.0039 0.4034 0.038 Uiso 1 1 calc R . . C14 C 0.7303(2) 0.0265(2) 0.3851(2) 0.0290(5) Uani 1 1 d . . . C15 C 0.7107(3) -0.0998(3) 0.3575(2) 0.0424(6) Uani 1 1 d . . . H15A H 0.6237 -0.1422 0.4045 0.064 Uiso 1 1 calc R . . H15B H 0.7869 -0.1598 0.3750 0.064 Uiso 1 1 calc R . . H15C H 0.7090 -0.0792 0.2750 0.064 Uiso 1 1 calc R . . Cl1' Cl 0.48628(6) 0.75596(6) 0.96718(5) 0.03509(16) Uani 1 1 d . . . O1' O 0.85949(15) 0.60033(15) 0.51251(14) 0.0279(4) Uani 1 1 d . . . C1' C 0.5598(2) 0.6953(2) 0.85224(19) 0.0255(5) Uani 1 1 d . . . C2' C 0.5101(2) 0.5786(2) 0.84767(19) 0.0250(5) Uani 1 1 d . . . H2' H 0.4344 0.5339 0.9051 0.030 Uiso 1 1 calc R . . C3' C 0.6679(2) 0.7644(2) 0.7680(2) 0.0277(5) Uani 1 1 d . . . H3' H 0.7001 0.8452 0.7714 0.033 Uiso 1 1 calc R . . C4' C 0.5717(2) 0.5274(2) 0.75857(19) 0.0226(4) Uani 1 1 d . . . H4' H 0.5382 0.4471 0.7551 0.027 Uiso 1 1 calc R . . C5' C 0.7274(2) 0.7128(2) 0.6790(2) 0.0248(5) Uani 1 1 d . . . H5' H 0.8005 0.7599 0.6200 0.030 Uiso 1 1 calc R . . C6' C 0.6824(2) 0.5929(2) 0.67392(18) 0.0208(4) Uani 1 1 d . . . C7' C 0.7576(2) 0.5407(2) 0.57807(19) 0.0211(4) Uani 1 1 d . . . C8' C 0.7109(2) 0.4127(2) 0.56370(18) 0.0207(4) Uani 1 1 d . . . H8' H 0.6109 0.4193 0.5618 0.025 Uiso 1 1 calc R . . C9' C 0.7318(2) 0.2960(2) 0.66600(18) 0.0208(4) Uani 1 1 d . . . C10' C 0.8598(2) 0.2725(2) 0.69564(19) 0.0242(5) Uani 1 1 d . . . H10' H 0.9365 0.3253 0.6476 0.029 Uiso 1 1 calc R . . C11' C 0.6233(2) 0.2112(2) 0.73387(19) 0.0244(5) Uani 1 1 d . . . H11' H 0.5363 0.2221 0.7126 0.029 Uiso 1 1 calc R . . C12' C 0.8770(2) 0.1729(2) 0.7945(2) 0.0292(5) Uani 1 1 d . . . H12' H 0.9651 0.1589 0.8135 0.035 Uiso 1 1 calc R . . C13' C 0.6408(2) 0.1114(2) 0.8318(2) 0.0290(5) Uani 1 1 d . . . H13' H 0.5659 0.0541 0.8765 0.035 Uiso 1 1 calc R . . C14' C 0.7669(2) 0.0936(2) 0.8659(2) 0.0284(5) Uani 1 1 d . . . C15' C 0.7808(3) -0.0034(3) 0.9806(2) 0.0428(6) Uani 1 1 d . . . H15D H 0.8757 -0.0349 0.9755 0.064 Uiso 1 1 calc R . . H15E H 0.7183 -0.0784 0.9993 0.064 Uiso 1 1 calc R . . H15F H 0.7576 0.0402 1.0416 0.064 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 Cl1 0.0448(3) 0.0387(4) 0.0221(3) -0.0100(3) 0.0036(2) -0.0098(3) O1 0.0212(8) 0.0308(9) 0.0295(9) -0.0085(7) -0.0056(6) 0.0049(6) C1 0.0336(12) 0.0247(12) 0.0200(11) -0.0096(9) 0.0004(9) -0.0067(9) C2 0.0398(13) 0.0262(12) 0.0208(11) -0.0061(10) -0.0077(10) 0.0064(10) C3 0.0225(11) 0.0351(13) 0.0245(12) -0.0135(10) -0.0040(9) -0.0011(9) C4 0.0282(11) 0.0269(12) 0.0260(12) -0.0088(10) -0.0066(9) 0.0052(9) C5 0.0250(11) 0.0267(12) 0.0197(11) -0.0072(9) -0.0069(8) -0.0004(9) C6 0.0231(10) 0.0201(11) 0.0211(11) -0.0090(9) -0.0057(8) 0.0007(8) C7 0.0196(10) 0.0217(11) 0.0230(11) -0.0103(9) -0.0057(8) -0.0016(8) C8 0.0154(9) 0.0232(11) 0.0195(10) -0.0063(9) -0.0027(8) -0.0019(8) C9 0.0205(10) 0.0233(11) 0.0155(10) -0.0054(8) -0.0026(8) -0.0009(8) C10 0.0238(11) 0.0260(12) 0.0310(12) -0.0058(10) -0.0114(9) 0.0021(9) C11 0.0199(10) 0.0286(12) 0.0321(13) -0.0091(10) -0.0051(9) 0.0018(9) C12 0.0300(12) 0.0305(13) 0.0326(13) -0.0072(10) -0.0137(10) -0.0044(10) C13 0.0317(12) 0.0256(12) 0.0354(14) -0.0096(11) -0.0044(10) 0.0048(10) C14 0.0387(13) 0.0254(12) 0.0219(12) -0.0049(10) -0.0067(10) -0.0034(10) C15 0.0571(17) 0.0326(14) 0.0416(16) -0.0158(13) -0.0112(13) -0.0037(12) Cl1' 0.0452(3) 0.0319(3) 0.0305(3) -0.0177(3) -0.0005(3) -0.0009(3) O1' 0.0225(8) 0.0284(9) 0.0312(9) -0.0108(7) 0.0013(6) -0.0031(6) C1' 0.0291(11) 0.0267(12) 0.0239(11) -0.0122(10) -0.0070(9) 0.0046(9) C2' 0.0237(11) 0.0271(12) 0.0238(11) -0.0086(9) -0.0022(9) -0.0013(9) C3' 0.0286(12) 0.0252(12) 0.0322(13) -0.0125(10) -0.0068(10) -0.0007(9) C4' 0.0196(10) 0.0247(11) 0.0262(11) -0.0102(9) -0.0068(8) 0.0007(8) C5' 0.0205(10) 0.0237(11) 0.0295(12) -0.0076(10) -0.0042(9) -0.0012(8) C6' 0.0179(10) 0.0236(11) 0.0228(11) -0.0077(9) -0.0079(8) 0.0031(8) C7' 0.0157(10) 0.0246(11) 0.0236(11) -0.0071(9) -0.0057(8) 0.0014(8) C8' 0.0168(9) 0.0253(11) 0.0212(11) -0.0084(9) -0.0043(8) 0.0001(8) C9' 0.0223(10) 0.0221(11) 0.0204(11) -0.0104(9) -0.0036(8) 0.0005(8) C10' 0.0233(11) 0.0246(11) 0.0259(12) -0.0093(9) -0.0048(9) -0.0011(9) C11' 0.0224(10) 0.0262(12) 0.0258(11) -0.0115(10) -0.0014(9) -0.0028(9) C12' 0.0326(12) 0.0282(13) 0.0309(13) -0.0125(10) -0.0114(10) 0.0057(10) C13' 0.0348(12) 0.0217(12) 0.0282(12) -0.0094(10) 0.0019(10) -0.0042(9) C14' 0.0429(13) 0.0189(11) 0.0238(12) -0.0090(9) -0.0053(10) 0.0043(9) C15' 0.0620(18) 0.0305(14) 0.0324(14) -0.0037(12) -0.0126(13) 0.0078(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 Cl1 C1 1.737(2) . ? O1 C7 1.225(2) . ? C1 C2 1.384(3) . ? C1 C3 1.386(3) . ? C2 C4 1.377(3) . ? C2 H2 0.9500 . ? C3 C5 1.385(3) . ? C3 H3 0.9500 . ? C4 C6 1.393(3) . ? C4 H4 0.9500 . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 C7 1.491(3) . ? C7 C8 1.525(3) . ? C8 C9 1.523(3) . ? C8 C8' 1.537(3) . ? C8 H8 1.0000 . ? C9 C11 1.387(3) . ? C9 C10 1.391(3) . ? C10 C12 1.388(3) . ? C10 H10 0.9500 . ? C11 C13 1.390(3) . ? C11 H11 0.9500 . ? C12 C14 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.514(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? Cl1' C1' 1.739(2) . ? O1' C7' 1.223(3) . ? C1' C2' 1.383(3) . ? C1' C3' 1.387(3) . ? C2' C4' 1.385(3) . ? C2' H2' 0.9500 . ? C3' C5' 1.381(3) . ? C3' H3' 0.9500 . ? C4' C6' 1.394(3) . ? C4' H4' 0.9500 . ? C5' C6' 1.399(3) . ? C5' H5' 0.9500 . ? C6' C7' 1.496(3) . ? C7' C8' 1.534(3) . ? C8' C9' 1.521(3) . ? C8' H8' 1.0000 . ? C9' C10' 1.391(3) . ? C9' C11' 1.394(3) . ? C10' C12' 1.388(3) . ? C10' H10' 0.9500 . ? C11' C13' 1.382(3) . ? C11' H11' 0.9500 . ? C12' C14' 1.389(3) . ? C12' H12' 0.9500 . ? C13' C14' 1.395(3) . ? C13' H13' 0.9500 . ? C14' C15' 1.508(3) . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 121.0(2) . . ? C2 C1 Cl1 119.02(18) . . ? C3 C1 Cl1 119.97(18) . . ? C4 C2 C1 119.5(2) . . ? C4 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C5 C3 C1 118.9(2) . . ? C5 C3 H3 120.6 . . ? C1 C3 H3 120.6 . . ? C2 C4 C6 120.9(2) . . ? C2 C4 H4 119.6 . . ? C6 C4 H4 119.6 . . ? C3 C5 C6 121.0(2) . . ? C3 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C4 C6 C5 118.6(2) . . ? C4 C6 C7 118.55(18) . . ? C5 C6 C7 122.82(19) . . ? O1 C7 C6 119.80(19) . . ? O1 C7 C8 120.28(19) . . ? C6 C7 C8 119.89(17) . . ? C9 C8 C7 109.22(16) . . ? C9 C8 C8' 114.02(17) . . ? C7 C8 C8' 110.16(16) . . ? C9 C8 H8 107.7 . . ? C7 C8 H8 107.7 . . ? C8' C8 H8 107.7 . . ? C11 C9 C10 117.6(2) . . ? C11 C9 C8 120.57(18) . . ? C10 C9 C8 121.82(18) . . ? C12 C10 C9 120.8(2) . . ? C12 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C9 C11 C13 121.5(2) . . ? C9 C11 H11 119.3 . . ? C13 C11 H11 119.3 . . ? C14 C12 C10 121.5(2) . . ? C14 C12 H12 119.3 . . ? C10 C12 H12 119.3 . . ? C14 C13 C11 120.9(2) . . ? C14 C13 H13 119.6 . . ? C11 C13 H13 119.6 . . ? C13 C14 C12 117.7(2) . . ? C13 C14 C15 121.3(2) . . ? C12 C14 C15 120.9(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C2' C1' C3' 121.6(2) . . ? C2' C1' Cl1' 119.19(18) . . ? C3' C1' Cl1' 119.24(17) . . ? C1' C2' C4' 119.4(2) . . ? C1' C2' H2' 120.3 . . ? C4' C2' H2' 120.3 . . ? C5' C3' C1' 118.4(2) . . ? C5' C3' H3' 120.8 . . ? C1' C3' H3' 120.8 . . ? C2' C4' C6' 120.5(2) . . ? C2' C4' H4' 119.8 . . ? C6' C4' H4' 119.8 . . ? C3' C5' C6' 121.4(2) . . ? C3' C5' H5' 119.3 . . ? C6' C5' H5' 119.3 . . ? C4' C6' C5' 118.69(19) . . ? C4' C6' C7' 123.41(19) . . ? C5' C6' C7' 117.90(19) . . ? O1' C7' C6' 118.80(19) . . ? O1' C7' C8' 120.17(18) . . ? C6' C7' C8' 121.01(18) . . ? C9' C8' C7' 109.83(16) . . ? C9' C8' C8 112.01(17) . . ? C7' C8' C8 108.45(17) . . ? C9' C8' H8' 108.8 . . ? C7' C8' H8' 108.8 . . ? C8 C8' H8' 108.8 . . ? C10' C9' C11' 118.1(2) . . ? C10' C9' C8' 120.60(19) . . ? C11' C9' C8' 121.26(18) . . ? C12' C10' C9' 120.9(2) . . ? C12' C10' H10' 119.6 . . ? C9' C10' H10' 119.6 . . ? C13' C11' C9' 120.8(2) . . ? C13' C11' H11' 119.6 . . ? C9' C11' H11' 119.6 . . ? C10' C12' C14' 120.8(2) . . ? C10' C12' H12' 119.6 . . ? C14' C12' H12' 119.6 . . ? C11' C13' C14' 121.0(2) . . ? C11' C13' H13' 119.5 . . ? C14' C13' H13' 119.5 . . ? C12' C14' C13' 118.1(2) . . ? C12' C14' C15' 121.0(2) . . ? C13' C14' C15' 120.8(2) . . ? C14' C15' H15D 109.5 . . ? C14' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C14' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 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 C3 C1 C2 C4 3.7(3) . . . . ? Cl1 C1 C2 C4 -175.83(17) . . . . ? C2 C1 C3 C5 -1.5(3) . . . . ? Cl1 C1 C3 C5 178.06(16) . . . . ? C1 C2 C4 C6 -2.4(3) . . . . ? C1 C3 C5 C6 -2.1(3) . . . . ? C2 C4 C6 C5 -1.1(3) . . . . ? C2 C4 C6 C7 177.6(2) . . . . ? C3 C5 C6 C4 3.4(3) . . . . ? C3 C5 C6 C7 -175.29(19) . . . . ? C4 C6 C7 O1 -10.4(3) . . . . ? C5 C6 C7 O1 168.24(19) . . . . ? C4 C6 C7 C8 167.95(19) . . . . ? C5 C6 C7 C8 -13.4(3) . . . . ? O1 C7 C8 C9 100.1(2) . . . . ? C6 C7 C8 C9 -78.3(2) . . . . ? O1 C7 C8 C8' -25.9(3) . . . . ? C6 C7 C8 C8' 155.73(17) . . . . ? C7 C8 C9 C11 123.8(2) . . . . ? C8' C8 C9 C11 -112.5(2) . . . . ? C7 C8 C9 C10 -54.8(3) . . . . ? C8' C8 C9 C10 68.9(3) . . . . ? C11 C9 C10 C12 -0.7(3) . . . . ? C8 C9 C10 C12 178.0(2) . . . . ? C10 C9 C11 C13 0.9(3) . . . . ? C8 C9 C11 C13 -177.8(2) . . . . ? C9 C10 C12 C14 -0.4(4) . . . . ? C9 C11 C13 C14 0.0(4) . . . . ? C11 C13 C14 C12 -1.0(4) . . . . ? C11 C13 C14 C15 177.7(2) . . . . ? C10 C12 C14 C13 1.3(4) . . . . ? C10 C12 C14 C15 -177.5(2) . . . . ? C3' C1' C2' C4' 1.7(3) . . . . ? Cl1' C1' C2' C4' -177.63(16) . . . . ? C2' C1' C3' C5' -1.0(3) . . . . ? Cl1' C1' C3' C5' 178.26(17) . . . . ? C1' C2' C4' C6' -0.2(3) . . . . ? C1' C3' C5' C6' -1.0(3) . . . . ? C2' C4' C6' C5' -1.8(3) . . . . ? C2' C4' C6' C7' 177.43(19) . . . . ? C3' C5' C6' C4' 2.4(3) . . . . ? C3' C5' C6' C7' -176.8(2) . . . . ? C4' C6' C7' O1' -174.96(19) . . . . ? C5' C6' C7' O1' 4.2(3) . . . . ? C4' C6' C7' C8' 3.3(3) . . . . ? C5' C6' C7' C8' -177.52(18) . . . . ? O1' C7' C8' C9' 111.6(2) . . . . ? C6' C7' C8' C9' -66.6(2) . . . . ? O1' C7' C8' C8 -11.1(3) . . . . ? C6' C7' C8' C8 170.70(17) . . . . ? C9 C8 C8' C9' 51.9(2) . . . . ? C7 C8 C8' C9' 175.10(16) . . . . ? C9 C8 C8' C7' 173.27(16) . . . . ? C7 C8 C8' C7' -63.5(2) . . . . ? C7' C8' C9' C10' -54.5(2) . . . . ? C8 C8' C9' C10' 66.1(2) . . . . ? C7' C8' C9' C11' 124.3(2) . . . . ? C8 C8' C9' C11' -115.1(2) . . . . ? C11' C9' C10' C12' -4.3(3) . . . . ? C8' C9' C10' C12' 174.58(19) . . . . ? C10' C9' C11' C13' 3.7(3) . . . . ? C8' C9' C11' C13' -175.10(19) . . . . ? C9' C10' C12' C14' 0.4(3) . . . . ? C9' C11' C13' C14' 0.6(3) . . . . ? C10' C12' C14' C13' 3.9(3) . . . . ? C10' C12' C14' C15' -172.5(2) . . . . ? C11' C13' C14' C12' -4.4(3) . . . . ? C11' C13' C14' C15' 172.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.540 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.061 # Attachment 'compound 2r.cif' data_ds0503 _database_code_depnum_ccdc_archive 'CCDC 609162' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 O4' _chemical_formula_sum 'C18 H18 O4' _chemical_formula_weight 298.32 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 8.9596(2) _cell_length_b 17.7193(6) _cell_length_c 10.0126(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.631(2) _cell_angle_gamma 90.00 _cell_volume 1538.03(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8856 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; No unusual features. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11178 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3503 _reflns_number_gt 2739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0344P)^2^+0.5855P] 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 3503 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 -0.13173(11) 0.45452(5) 0.87661(10) 0.0272(2) Uani 1 1 d . . . C1 C -0.22571(18) 0.52052(8) 0.88388(17) 0.0332(3) Uani 1 1 d . . . H1A H -0.1851 0.5464 0.9721 0.050 Uiso 1 1 calc R . . H1B H -0.3323 0.5048 0.8766 0.050 Uiso 1 1 calc R . . H1C H -0.2231 0.5549 0.8078 0.050 Uiso 1 1 calc R . . O2 O -0.28613(11) 0.42840(6) 0.66785(10) 0.0284(2) Uani 1 1 d . . . C2 C -0.17560(14) 0.41348(7) 0.76106(13) 0.0201(3) Uani 1 1 d . . . C3 C -0.06615(14) 0.34812(7) 0.76205(13) 0.0192(3) Uani 1 1 d . . . H3 H -0.0244 0.3312 0.8597 0.023 Uiso 1 1 calc R . . C4 C 0.06844(14) 0.37344(7) 0.70529(13) 0.0199(3) Uani 1 1 d . . . C5 C 0.04293(16) 0.40354(8) 0.57297(14) 0.0256(3) Uani 1 1 d . . . H5 H -0.0596 0.4107 0.5188 0.031 Uiso 1 1 calc R . . C6 C 0.16632(17) 0.42317(8) 0.51977(16) 0.0302(3) Uani 1 1 d . . . H6 H 0.1478 0.4436 0.4293 0.036 Uiso 1 1 calc R . . C7 C 0.31647(16) 0.41314(8) 0.59790(16) 0.0301(3) Uani 1 1 d . . . H7 H 0.4008 0.4264 0.5611 0.036 Uiso 1 1 calc R . . C8 C 0.34277(16) 0.38372(8) 0.72952(16) 0.0300(3) Uani 1 1 d . . . H8 H 0.4455 0.3770 0.7836 0.036 Uiso 1 1 calc R . . C9 C 0.21930(15) 0.36392(8) 0.78307(15) 0.0247(3) Uani 1 1 d . . . H9 H 0.2383 0.3437 0.8737 0.030 Uiso 1 1 calc R . . O1' O -0.38640(11) 0.21586(6) 0.63142(10) 0.0271(2) Uani 1 1 d . . . C1' C -0.52445(16) 0.18903(9) 0.66695(16) 0.0321(3) Uani 1 1 d . . . H1'A H -0.5709 0.1482 0.6040 0.048 Uiso 1 1 calc R . . H1'B H -0.5983 0.2306 0.6589 0.048 Uiso 1 1 calc R . . H1'C H -0.4974 0.1701 0.7620 0.048 Uiso 1 1 calc R . . O2' O -0.31765(11) 0.27809(6) 0.83330(10) 0.0295(2) Uani 1 1 d . . . C2' C -0.29284(14) 0.25970(7) 0.72510(13) 0.0209(3) Uani 1 1 d . . . C3' C -0.15045(14) 0.28105(7) 0.67743(13) 0.0191(3) Uani 1 1 d . . . H3' H -0.1832 0.2961 0.5781 0.023 Uiso 1 1 calc R . . C4' C -0.04436(14) 0.21287(7) 0.69092(13) 0.0192(3) Uani 1 1 d . . . C5' C 0.01679(14) 0.19153(8) 0.58195(13) 0.0210(3) Uani 1 1 d . . . H5' H -0.0085 0.2195 0.4983 0.025 Uiso 1 1 calc R . . C6' C 0.11446(15) 0.12968(8) 0.59474(14) 0.0241(3) Uani 1 1 d . . . H6' H 0.1550 0.1153 0.5195 0.029 Uiso 1 1 calc R . . C7' C 0.15300(15) 0.08890(8) 0.71637(15) 0.0258(3) Uani 1 1 d . . . H7' H 0.2195 0.0465 0.7246 0.031 Uiso 1 1 calc R . . C8' C 0.09425(16) 0.11019(8) 0.82645(14) 0.0261(3) Uani 1 1 d . . . H8' H 0.1212 0.0826 0.9104 0.031 Uiso 1 1 calc R . . C9' C -0.00387(15) 0.17188(8) 0.81369(13) 0.0232(3) Uani 1 1 d . . . H9' H -0.0438 0.1863 0.8893 0.028 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 0.0259(5) 0.0248(5) 0.0282(5) -0.0077(4) 0.0021(4) 0.0047(4) C1 0.0353(8) 0.0255(8) 0.0389(8) -0.0073(6) 0.0096(7) 0.0067(6) O2 0.0252(5) 0.0316(6) 0.0260(5) -0.0006(4) 0.0021(4) 0.0070(4) C2 0.0190(6) 0.0216(7) 0.0210(6) 0.0004(5) 0.0078(5) -0.0022(5) C3 0.0184(6) 0.0205(7) 0.0184(6) 0.0000(5) 0.0042(5) 0.0001(5) C4 0.0199(6) 0.0162(6) 0.0244(7) -0.0029(5) 0.0069(5) -0.0006(5) C5 0.0226(7) 0.0273(7) 0.0267(7) 0.0019(6) 0.0059(6) -0.0012(6) C6 0.0361(8) 0.0280(8) 0.0303(8) 0.0017(6) 0.0153(6) -0.0033(6) C7 0.0272(7) 0.0239(7) 0.0451(9) -0.0077(6) 0.0199(7) -0.0058(6) C8 0.0188(6) 0.0285(8) 0.0422(9) -0.0065(7) 0.0069(6) -0.0003(6) C9 0.0223(7) 0.0228(7) 0.0282(7) -0.0014(6) 0.0048(6) 0.0013(5) O1' 0.0218(5) 0.0336(6) 0.0273(5) -0.0063(4) 0.0090(4) -0.0088(4) C1' 0.0231(7) 0.0362(9) 0.0395(9) -0.0059(7) 0.0126(6) -0.0092(6) O2' 0.0268(5) 0.0379(6) 0.0270(5) -0.0069(4) 0.0129(4) -0.0049(4) C2' 0.0200(6) 0.0207(7) 0.0215(7) 0.0015(5) 0.0046(5) 0.0018(5) C3' 0.0184(6) 0.0221(7) 0.0168(6) -0.0004(5) 0.0046(5) -0.0003(5) C4' 0.0171(6) 0.0191(7) 0.0212(6) -0.0015(5) 0.0044(5) -0.0038(5) C5' 0.0199(6) 0.0239(7) 0.0193(6) 0.0001(5) 0.0050(5) -0.0023(5) C6' 0.0218(6) 0.0258(7) 0.0268(7) -0.0041(6) 0.0099(5) -0.0018(5) C7' 0.0221(7) 0.0222(7) 0.0333(8) -0.0001(6) 0.0076(6) 0.0013(5) C8' 0.0285(7) 0.0248(7) 0.0240(7) 0.0038(6) 0.0047(6) 0.0001(6) C9' 0.0262(7) 0.0247(7) 0.0198(6) -0.0007(5) 0.0076(5) -0.0007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3388(16) . ? O1 C1 1.4535(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C2 1.2060(15) . ? C2 C3 1.5160(18) . ? C3 C4 1.5247(17) . ? C3 C3' 1.5419(18) . ? C3 H3 1.0000 . ? C4 C9 1.3893(18) . ? C4 C5 1.3925(19) . ? C5 C6 1.3873(19) . ? C5 H5 0.9500 . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C7 C8 1.381(2) . ? C7 H7 0.9500 . ? C8 C9 1.3906(19) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? O1' C2' 1.3375(16) . ? O1' C1' 1.4508(16) . ? C1' H1'A 0.9800 . ? C1' H1'B 0.9800 . ? C1' H1'C 0.9800 . ? O2' C2' 1.2045(16) . ? C2' C3' 1.5186(17) . ? C3' C4' 1.5219(18) . ? C3' H3' 1.0000 . ? C4' C5' 1.3913(18) . ? C4' C9' 1.3946(18) . ? C5' C6' 1.3880(19) . ? C5' H5' 0.9500 . ? C6' C7' 1.383(2) . ? C6' H6' 0.9500 . ? C7' C8' 1.3883(19) . ? C7' H7' 0.9500 . ? C8' C9' 1.3884(19) . ? C8' H8' 0.9500 . ? C9' H9' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 115.66(11) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.65(12) . . ? O2 C2 C3 125.16(12) . . ? O1 C2 C3 111.17(11) . . ? C2 C3 C4 110.11(10) . . ? C2 C3 C3' 111.04(10) . . ? C4 C3 C3' 110.23(10) . . ? C2 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? C3' C3 H3 108.5 . . ? C9 C4 C5 118.85(12) . . ? C9 C4 C3 120.29(12) . . ? C5 C4 C3 120.81(11) . . ? C6 C5 C4 120.41(13) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.34(14) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 119.62(13) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.17(13) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 120.62(13) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C2' O1' C1' 116.13(10) . . ? O1' C1' H1'A 109.5 . . ? O1' C1' H1'B 109.5 . . ? H1'A C1' H1'B 109.5 . . ? O1' C1' H1'C 109.5 . . ? H1'A C1' H1'C 109.5 . . ? H1'B C1' H1'C 109.5 . . ? O2' C2' O1' 124.23(12) . . ? O2' C2' C3' 125.16(12) . . ? O1' C2' C3' 110.59(10) . . ? C2' C3' C4' 109.26(10) . . ? C2' C3' C3 110.68(10) . . ? C4' C3' C3 110.78(10) . . ? C2' C3' H3' 108.7 . . ? C4' C3' H3' 108.7 . . ? C3 C3' H3' 108.7 . . ? C5' C4' C9' 118.90(12) . . ? C5' C4' C3' 120.47(11) . . ? C9' C4' C3' 120.61(11) . . ? C6' C5' C4' 120.42(12) . . ? C6' C5' H5' 119.8 . . ? C4' C5' H5' 119.8 . . ? C7' C6' C5' 120.34(12) . . ? C7' C6' H6' 119.8 . . ? C5' C6' H6' 119.8 . . ? C6' C7' C8' 119.80(13) . . ? C6' C7' H7' 120.1 . . ? C8' C7' H7' 120.1 . . ? C7' C8' C9' 119.94(13) . . ? C7' C8' H8' 120.0 . . ? C9' C8' H8' 120.0 . . ? C8' C9' C4' 120.59(12) . . ? C8' C9' H9' 119.7 . . ? C4' C9' H9' 119.7 . . ? 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 C1 O1 C2 O2 -0.69(18) . . . . ? C1 O1 C2 C3 177.70(11) . . . . ? O2 C2 C3 C4 91.57(15) . . . . ? O1 C2 C3 C4 -86.79(13) . . . . ? O2 C2 C3 C3' -30.80(17) . . . . ? O1 C2 C3 C3' 150.84(10) . . . . ? C2 C3 C4 C9 124.49(13) . . . . ? C3' C3 C4 C9 -112.66(13) . . . . ? C2 C3 C4 C5 -58.16(16) . . . . ? C3' C3 C4 C5 64.68(15) . . . . ? C9 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C6 -176.98(13) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 -0.3(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C5 C4 C9 C8 -0.3(2) . . . . ? C3 C4 C9 C8 177.06(12) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C1' O1' C2' O2' -0.9(2) . . . . ? C1' O1' C2' C3' 177.73(11) . . . . ? O2' C2' C3' C4' 104.87(15) . . . . ? O1' C2' C3' C4' -73.70(13) . . . . ? O2' C2' C3' C3 -17.38(18) . . . . ? O1' C2' C3' C3 164.06(11) . . . . ? C2 C3 C3' C2' -52.81(14) . . . . ? C4 C3 C3' C2' -175.12(10) . . . . ? C2 C3 C3' C4' -174.17(10) . . . . ? C4 C3 C3' C4' 63.53(13) . . . . ? C2' C3' C4' C5' 131.58(12) . . . . ? C3 C3' C4' C5' -106.23(13) . . . . ? C2' C3' C4' C9' -49.97(15) . . . . ? C3 C3' C4' C9' 72.21(15) . . . . ? C9' C4' C5' C6' 1.04(19) . . . . ? C3' C4' C5' C6' 179.51(12) . . . . ? C4' C5' C6' C7' -0.5(2) . . . . ? C5' C6' C7' C8' -0.3(2) . . . . ? C6' C7' C8' C9' 0.5(2) . . . . ? C7' C8' C9' C4' 0.1(2) . . . . ? C5' C4' C9' C8' -0.83(19) . . . . ? C3' C4' C9' C8' -179.30(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.228 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051 # Attachment 'compound 2s.cif' data_ds0402 _database_code_depnum_ccdc_archive 'CCDC 609163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 O4' _chemical_formula_sum 'C16 H12 O4' _chemical_formula_weight 268.26 _chemical_absolute_configuration ; 671 Friedel pairs were averaged for the refinement ; 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 Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 9.7780(7) _cell_length_b 13.5482(10) _cell_length_c 9.4858(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1256.62(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10926 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; No unusual features ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5041 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.46 _reflns_number_total 764 _reflns_number_gt 671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0301P)^2^+0.4218P] 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 764 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.122 _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 0.08998(16) -0.07771(11) 0.89019(17) 0.0347(4) Uani 1 1 d . . . O2 O 0.19663(15) 0.04892(12) 0.7789(2) 0.0391(4) Uani 1 1 d . . . C1 C 0.0717(3) -0.02136(19) 1.0180(3) 0.0390(6) Uani 1 1 d . . . H1A H 0.1400 0.0325 1.0225 0.047 Uiso 1 1 calc R . . H1B H 0.0845 -0.0645 1.1012 0.047 Uiso 1 1 calc R . . C2 C 0.1398(2) -0.02995(16) 0.7766(3) 0.0320(5) Uani 1 1 d . . . C3 C 0.1106(2) -0.08919(17) 0.6467(2) 0.0316(5) Uani 1 1 d . . . C4 C 0.1653(2) -0.18424(18) 0.6372(3) 0.0386(6) Uani 1 1 d . . . H4 H 0.2172 -0.2103 0.7133 0.046 Uiso 1 1 calc R . . C5 C 0.1442(3) -0.24049(18) 0.5175(3) 0.0453(6) Uani 1 1 d . . . H5 H 0.1851 -0.3038 0.5093 0.054 Uiso 1 1 calc R . . C6 C 0.0636(3) -0.2043(2) 0.4102(3) 0.0454(6) Uani 1 1 d . . . H6 H 0.0471 -0.2436 0.3291 0.054 Uiso 1 1 calc R . . C7 C 0.0068(2) -0.1113(2) 0.4197(3) 0.0406(6) Uani 1 1 d . . . H7 H -0.0495 -0.0878 0.3453 0.049 Uiso 1 1 calc R . . C8 C 0.0306(2) -0.05063(17) 0.5377(2) 0.0337(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0359(9) 0.0354(8) 0.0326(9) 0.0000(7) 0.0006(8) 0.0030(7) O2 0.0325(8) 0.0414(9) 0.0435(9) -0.0042(9) -0.0012(8) -0.0076(6) C1 0.0415(13) 0.0449(14) 0.0304(12) -0.0022(12) 0.0009(12) 0.0053(11) C2 0.0222(9) 0.0379(12) 0.0359(12) -0.0001(12) -0.0004(10) 0.0038(8) C3 0.0244(11) 0.0364(12) 0.0340(13) -0.0008(11) 0.0039(8) -0.0042(9) C4 0.0305(11) 0.0373(12) 0.0479(15) -0.0016(11) 0.0030(11) -0.0020(10) C5 0.0412(13) 0.0354(13) 0.0594(16) -0.0094(14) 0.0086(14) -0.0031(10) C6 0.0409(14) 0.0491(15) 0.0463(15) -0.0162(14) 0.0042(12) -0.0118(11) C7 0.0318(11) 0.0548(15) 0.0353(13) -0.0037(12) 0.0009(10) -0.0076(11) C8 0.0262(10) 0.0409(12) 0.0341(12) -0.0018(11) 0.0052(10) -0.0071(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 O1 C2 1.348(3) . ? O1 C1 1.444(3) . ? O2 C2 1.205(3) . ? C1 C1 1.517(5) 2 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.498(3) . ? C3 C4 1.397(3) . ? C3 C8 1.398(3) . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.377(4) . ? C5 H5 0.9500 . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C7 C8 1.408(3) . ? C7 H7 0.9500 . ? C8 C8 1.496(5) 2 ? 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 O1 C1 117.53(17) . . ? O1 C1 C1 108.43(16) . 2 ? O1 C1 H1A 110.0 . . ? C1 C1 H1A 110.0 2 . ? O1 C1 H1B 110.0 . . ? C1 C1 H1B 110.0 2 . ? H1A C1 H1B 108.4 . . ? O2 C2 O1 125.3(2) . . ? O2 C2 C3 125.3(2) . . ? O1 C2 C3 109.35(17) . . ? C4 C3 C8 120.7(2) . . ? C4 C3 C2 118.3(2) . . ? C8 C3 C2 121.00(19) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.5(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C3 C8 C7 117.5(2) . . ? C3 C8 C8 124.48(16) . 2 ? C7 C8 C8 117.99(18) . 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 C2 O1 C1 C1 90.3(3) . . . 2 ? C1 O1 C2 O2 16.4(3) . . . . ? C1 O1 C2 C3 -162.32(18) . . . . ? O2 C2 C3 C4 120.8(2) . . . . ? O1 C2 C3 C4 -60.5(2) . . . . ? O2 C2 C3 C8 -59.2(3) . . . . ? O1 C2 C3 C8 119.5(2) . . . . ? C8 C3 C4 C5 1.9(3) . . . . ? C2 C3 C4 C5 -178.1(2) . . . . ? C3 C4 C5 C6 -3.0(3) . . . . ? C4 C5 C6 C7 1.7(4) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C4 C3 C8 C7 0.5(3) . . . . ? C2 C3 C8 C7 -179.4(2) . . . . ? C4 C3 C8 C8 -179.1(2) . . . 2 ? C2 C3 C8 C8 0.9(4) . . . 2 ? C6 C7 C8 C3 -1.8(3) . . . . ? C6 C7 C8 C8 177.8(2) . . . 2 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.123 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.039 # Attachment 'compound 2t.cif' data_ds0403 _database_code_depnum_ccdc_archive 'CCDC 609164' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 O4' _chemical_formula_sum 'C20 H12 O4' _chemical_formula_weight 316.30 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 0.0016 '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 9.3998(2) _cell_length_b 11.4953(3) _cell_length_c 13.9452(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.2730(10) _cell_angle_gamma 90.00 _cell_volume 1494.70(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6639 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11656 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3415 _reflns_number_gt 2715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0395P)^2^+0.5216P] 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 3415 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.31859(10) 0.31155(8) 0.20319(7) 0.0270(2) Uani 1 1 d . . . O2 O 0.13392(11) 0.25696(9) 0.28252(8) 0.0348(3) Uani 1 1 d . . . C1 C 0.40540(17) 0.60029(14) 0.30485(11) 0.0349(4) Uani 1 1 d . . . H1 H 0.4808 0.6378 0.3451 0.042 Uiso 1 1 calc R . . C2 C 0.41563(15) 0.48286(14) 0.28408(10) 0.0302(3) Uani 1 1 d . . . H2 H 0.4980 0.4398 0.3098 0.036 Uiso 1 1 calc R . . C3 C 0.30524(15) 0.42869(13) 0.22574(10) 0.0265(3) Uani 1 1 d . . . C4 C 0.20902(15) 0.23785(13) 0.22080(10) 0.0271(3) Uani 1 1 d . . . C5 C 0.19840(14) 0.13663(12) 0.15433(11) 0.0274(3) Uani 1 1 d . . . C6 C 0.14481(16) 0.03364(13) 0.18906(12) 0.0337(3) Uani 1 1 d . . . H6 H 0.1181 0.0314 0.2525 0.040 Uiso 1 1 calc R . . C7 C 0.13037(18) -0.06492(14) 0.13204(14) 0.0410(4) Uani 1 1 d . . . H7 H 0.0942 -0.1347 0.1562 0.049 Uiso 1 1 calc R . . C8 C 0.16899(18) -0.06142(14) 0.03937(14) 0.0420(4) Uani 1 1 d . . . H8 H 0.1609 -0.1294 0.0003 0.050 Uiso 1 1 calc R . . C9 C 0.21933(17) 0.04106(13) 0.00376(12) 0.0361(4) Uani 1 1 d . . . H9 H 0.2441 0.0426 -0.0602 0.043 Uiso 1 1 calc R . . C10 C 0.23451(15) 0.14188(13) 0.05932(11) 0.0278(3) Uani 1 1 d . . . O1' O 0.06964(10) 0.44275(9) 0.12873(8) 0.0313(3) Uani 1 1 d . . . O2' O -0.03080(11) 0.31858(9) 0.02217(8) 0.0364(3) Uani 1 1 d . . . C1' C 0.28551(17) 0.66306(14) 0.26700(12) 0.0363(4) Uani 1 1 d . . . H1' H 0.2774 0.7429 0.2832 0.044 Uiso 1 1 calc R . . C2' C 0.17726(16) 0.60974(13) 0.20552(11) 0.0332(3) Uani 1 1 d . . . H2' H 0.0960 0.6532 0.1784 0.040 Uiso 1 1 calc R . . C3' C 0.18842(14) 0.49316(13) 0.18412(10) 0.0277(3) Uani 1 1 d . . . C4' C 0.07780(15) 0.36780(12) 0.05304(10) 0.0273(3) Uani 1 1 d . . . C5' C 0.21573(15) 0.35649(13) 0.01162(10) 0.0270(3) Uani 1 1 d . . . C6' C 0.26697(16) 0.45241(14) -0.03432(11) 0.0329(3) Uani 1 1 d . . . H6' H 0.2193 0.5252 -0.0335 0.040 Uiso 1 1 calc R . . C7' C 0.38783(18) 0.44146(15) -0.08130(11) 0.0385(4) Uani 1 1 d . . . H7' H 0.4214 0.5062 -0.1144 0.046 Uiso 1 1 calc R . . C8' C 0.45935(17) 0.33646(15) -0.07996(11) 0.0391(4) Uani 1 1 d . . . H8' H 0.5429 0.3293 -0.1113 0.047 Uiso 1 1 calc R . . C9' C 0.40951(16) 0.24134(14) -0.03292(10) 0.0325(3) Uani 1 1 d . . . H9' H 0.4603 0.1698 -0.0318 0.039 Uiso 1 1 calc R . . C10' C 0.28593(15) 0.24871(13) 0.01291(10) 0.0278(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0253(5) 0.0311(5) 0.0251(5) -0.0009(4) 0.0055(4) 0.0000(4) O2 0.0366(6) 0.0395(6) 0.0304(6) 0.0012(5) 0.0130(5) -0.0007(5) C1 0.0348(8) 0.0434(9) 0.0267(8) -0.0039(7) 0.0043(6) -0.0142(7) C2 0.0253(7) 0.0434(9) 0.0221(7) 0.0026(6) 0.0036(5) -0.0043(6) C3 0.0266(7) 0.0327(8) 0.0216(7) -0.0001(6) 0.0083(5) -0.0019(6) C4 0.0254(7) 0.0329(8) 0.0228(7) 0.0050(6) 0.0030(5) 0.0022(6) C5 0.0227(7) 0.0303(7) 0.0291(8) 0.0034(6) 0.0028(6) 0.0020(6) C6 0.0311(8) 0.0357(8) 0.0352(9) 0.0077(7) 0.0071(6) 0.0014(6) C7 0.0380(9) 0.0302(8) 0.0549(11) 0.0064(8) 0.0064(8) -0.0023(7) C8 0.0411(9) 0.0320(8) 0.0524(11) -0.0103(8) 0.0047(8) -0.0025(7) C9 0.0360(8) 0.0369(9) 0.0357(9) -0.0064(7) 0.0059(7) -0.0017(7) C10 0.0241(7) 0.0322(8) 0.0270(7) -0.0009(6) 0.0028(5) 0.0010(6) O1' 0.0227(5) 0.0360(6) 0.0346(6) -0.0070(5) 0.0008(4) -0.0008(4) O2' 0.0279(5) 0.0356(6) 0.0438(7) -0.0039(5) -0.0024(5) -0.0050(5) C1' 0.0414(9) 0.0336(8) 0.0352(9) -0.0067(7) 0.0093(7) -0.0074(7) C2' 0.0311(8) 0.0339(8) 0.0354(9) -0.0013(7) 0.0067(6) 0.0006(6) C3' 0.0227(6) 0.0355(8) 0.0251(7) -0.0026(6) 0.0042(5) -0.0045(6) C4' 0.0280(7) 0.0264(7) 0.0265(7) 0.0037(6) -0.0004(6) 0.0003(6) C5' 0.0277(7) 0.0331(8) 0.0194(7) -0.0006(6) -0.0008(5) -0.0036(6) C6' 0.0359(8) 0.0365(8) 0.0251(8) 0.0028(6) -0.0013(6) -0.0053(7) C7' 0.0422(9) 0.0463(10) 0.0272(8) 0.0044(7) 0.0048(7) -0.0150(8) C8' 0.0354(8) 0.0560(10) 0.0276(8) -0.0039(7) 0.0106(6) -0.0098(8) C9' 0.0333(8) 0.0415(9) 0.0235(7) -0.0049(6) 0.0065(6) -0.0009(7) C10' 0.0287(7) 0.0356(8) 0.0187(7) -0.0025(6) 0.0020(5) -0.0032(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3795(17) . ? O1 C3 1.3920(17) . ? O2 C4 1.2004(17) . ? C1 C1' 1.385(2) . ? C1 C2 1.387(2) . ? C1 H1 0.9500 . ? C2 C3 1.383(2) . ? C2 H2 0.9500 . ? C3 C3' 1.389(2) . ? C4 C5 1.483(2) . ? C5 C6 1.397(2) . ? C5 C10 1.410(2) . ? C6 C7 1.381(2) . ? C6 H6 0.9500 . ? C7 C8 1.386(3) . ? C7 H7 0.9500 . ? C8 C9 1.385(2) . ? C8 H8 0.9500 . ? C9 C10 1.391(2) . ? C9 H9 0.9500 . ? C10 C10' 1.497(2) . ? O1' C4' 1.3722(17) . ? O1' C3' 1.4002(16) . ? O2' C4' 1.1984(17) . ? C1' C2' 1.388(2) . ? C1' H1' 0.9500 . ? C2' C3' 1.380(2) . ? C2' H2' 0.9500 . ? C4' C5' 1.490(2) . ? C5' C6' 1.392(2) . ? C5' C10' 1.403(2) . ? C6' C7' 1.387(2) . ? C6' H6' 0.9500 . ? C7' C8' 1.381(2) . ? C7' H7' 0.9500 . ? C8' C9' 1.387(2) . ? C8' H8' 0.9500 . ? C9' C10' 1.397(2) . ? C9' H9' 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 C4 O1 C3 117.59(11) . . ? C1' C1 C2 120.14(14) . . ? C1' C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 119.64(14) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C3' 120.00(14) . . ? C2 C3 O1 119.08(13) . . ? C3' C3 O1 120.72(13) . . ? O2 C4 O1 122.37(13) . . ? O2 C4 C5 126.33(13) . . ? O1 C4 C5 111.30(12) . . ? C6 C5 C10 120.15(14) . . ? C6 C5 C4 116.54(13) . . ? C10 C5 C4 123.27(13) . . ? C7 C6 C5 120.61(15) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.64(15) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 120.04(15) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.64(15) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C5 117.88(14) . . ? C9 C10 C10' 117.30(13) . . ? C5 C10 C10' 124.81(13) . . ? C4' O1' C3' 124.46(11) . . ? C1 C1' C2' 120.20(15) . . ? C1 C1' H1' 119.9 . . ? C2' C1' H1' 119.9 . . ? C3' C2' C1' 119.52(15) . . ? C3' C2' H2' 120.2 . . ? C1' C2' H2' 120.2 . . ? C2' C3' C3 120.36(13) . . ? C2' C3' O1' 116.36(13) . . ? C3 C3' O1' 122.85(13) . . ? O2' C4' O1' 116.41(13) . . ? O2' C4' C5' 124.26(14) . . ? O1' C4' C5' 119.27(12) . . ? C6' C5' C10' 121.07(13) . . ? C6' C5' C4' 118.56(13) . . ? C10' C5' C4' 120.20(13) . . ? C7' C6' C5' 119.83(15) . . ? C7' C6' H6' 120.1 . . ? C5' C6' H6' 120.1 . . ? C8' C7' C6' 119.96(15) . . ? C8' C7' H7' 120.0 . . ? C6' C7' H7' 120.0 . . ? C7' C8' C9' 120.17(15) . . ? C7' C8' H8' 119.9 . . ? C9' C8' H8' 119.9 . . ? C8' C9' C10' 121.24(15) . . ? C8' C9' H9' 119.4 . . ? C10' C9' H9' 119.4 . . ? C9' C10' C5' 117.69(13) . . ? C9' C10' C10 118.73(13) . . ? C5' C10' C10 123.58(13) . . ? 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 C1' C1 C2 C3 -0.3(2) . . . . ? C1 C2 C3 C3' 3.4(2) . . . . ? C1 C2 C3 O1 178.20(12) . . . . ? C4 O1 C3 C2 127.19(13) . . . . ? C4 O1 C3 C3' -58.07(17) . . . . ? C3 O1 C4 O2 -27.36(19) . . . . ? C3 O1 C4 C5 152.28(11) . . . . ? O2 C4 C5 C6 -29.2(2) . . . . ? O1 C4 C5 C6 151.14(12) . . . . ? O2 C4 C5 C10 148.48(15) . . . . ? O1 C4 C5 C10 -31.14(18) . . . . ? C10 C5 C6 C7 1.8(2) . . . . ? C4 C5 C6 C7 179.65(14) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 C5 0.7(2) . . . . ? C8 C9 C10 C10' -178.33(14) . . . . ? C6 C5 C10 C9 -2.1(2) . . . . ? C4 C5 C10 C9 -179.70(13) . . . . ? C6 C5 C10 C10' 176.90(13) . . . . ? C4 C5 C10 C10' -0.7(2) . . . . ? C2 C1 C1' C2' -2.2(2) . . . . ? C1 C1' C2' C3' 1.4(2) . . . . ? C1' C2' C3' C3 1.7(2) . . . . ? C1' C2' C3' O1' 174.45(13) . . . . ? C2 C3 C3' C2' -4.2(2) . . . . ? O1 C3 C3' C2' -178.84(13) . . . . ? C2 C3 C3' O1' -176.42(13) . . . . ? O1 C3 C3' O1' 8.9(2) . . . . ? C4' O1' C3' C2' 136.75(14) . . . . ? C4' O1' C3' C3 -50.7(2) . . . . ? C3' O1' C4' O2' 169.17(13) . . . . ? C3' O1' C4' C5' -13.65(19) . . . . ? O2' C4' C5' C6' 111.69(17) . . . . ? O1' C4' C5' C6' -65.24(17) . . . . ? O2' C4' C5' C10' -63.60(19) . . . . ? O1' C4' C5' C10' 119.46(14) . . . . ? C10' C5' C6' C7' 1.2(2) . . . . ? C4' C5' C6' C7' -174.05(13) . . . . ? C5' C6' C7' C8' -1.9(2) . . . . ? C6' C7' C8' C9' 0.9(2) . . . . ? C7' C8' C9' C10' 0.8(2) . . . . ? C8' C9' C10' C5' -1.4(2) . . . . ? C8' C9' C10' C10 177.78(13) . . . . ? C6' C5' C10' C9' 0.4(2) . . . . ? C4' C5' C10' C9' 175.62(13) . . . . ? C6' C5' C10' C10 -178.72(13) . . . . ? C4' C5' C10' C10 -3.5(2) . . . . ? C9 C10 C10' C9' -50.75(19) . . . . ? C5 C10 C10' C9' 130.29(15) . . . . ? C9 C10 C10' C5' 128.42(15) . . . . ? C5 C10 C10' C5' -50.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.179 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.048