data_s92 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 O6' _chemical_formula_weight 356.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4814(3) _cell_length_b 7.2705(2) _cell_length_c 17.7911(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.2660(10) _cell_angle_gamma 90.00 _cell_volume 1738.99(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 26399 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'SORTAV (R.H. Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method '\w and \f scans to fill Ewald sphere' _diffrn_detector_area_resol_mean '9.091 pixels/mm' _diffrn_standards_number 'n/a' _diffrn_standards_interval_count 'n/a' _diffrn_standards_interval_time 'n/a' _diffrn_standards_decay_% 'n/a' _diffrn_reflns_number 14074 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3064 _reflns_number_gt 2597 _reflns_threshold_expression >2\s(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) ' ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0488P)^2^+0.4576P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3064 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 H5 H 0.5743(12) 0.753(2) 0.3717(9) 0.025(4) Uiso 1 1 d . . . H19 H 0.7816(11) 1.266(2) 0.5049(9) 0.019(4) Uiso 1 1 d . . . H18B H 0.7239(12) 1.303(2) 0.3491(9) 0.024(4) Uiso 1 1 d . . . H16 H 0.9573(11) 1.436(2) 0.4241(8) 0.020(4) Uiso 1 1 d . . . H3B H 0.7781(12) 0.929(2) 0.4794(8) 0.022(4) Uiso 1 1 d . . . H9 H 0.8278(12) 0.920(2) 0.2173(9) 0.025(4) Uiso 1 1 d . . . H7C H 0.3934(12) 0.631(2) 0.2295(9) 0.027(4) Uiso 1 1 d . . . H3A H 0.6731(11) 0.835(2) 0.4809(8) 0.022(4) Uiso 1 1 d . . . H20B H 0.6060(11) 1.465(2) 0.4530(9) 0.022(4) Uiso 1 1 d . . . H18A H 0.7893(11) 1.461(2) 0.3911(8) 0.021(4) Uiso 1 1 d . . . H7A H 0.4349(12) 0.794(2) 0.2854(9) 0.032(4) Uiso 1 1 d . . . H2 H 0.6084(12) 1.131(2) 0.4242(9) 0.027(4) Uiso 1 1 d . . . H12 H 0.9689(11) 0.836(2) 0.3303(8) 0.023(4) Uiso 1 1 d . . . H20A H 0.6877(12) 1.531(2) 0.5214(9) 0.035(4) Uiso 1 1 d . . . H7B H 0.4529(12) 0.585(2) 0.3109(10) 0.035(4) Uiso 1 1 d . . . H14A H 1.1294(14) 0.828(2) 0.2778(11) 0.045(5) Uiso 1 1 d . . . H14B H 1.2313(16) 0.797(3) 0.3282(11) 0.051(5) Uiso 1 1 d . . . H14C H 1.1246(16) 0.705(3) 0.3572(12) 0.060(6) Uiso 1 1 d . . . H4 H 0.6373(16) 0.676(3) 0.1328(11) 0.057(6) Uiso 1 1 d . . . H6 H 1.1851(16) 1.270(3) 0.4051(11) 0.052(6) Uiso 1 1 d . . . O3 O 0.53522(7) 0.66887(14) 0.22686(5) 0.0243(3) Uani 1 1 d . . . O6 O 1.13432(8) 1.32727(15) 0.42196(6) 0.0270(3) Uani 1 1 d . . . O2 O 0.57401(7) 1.02986(14) 0.57606(5) 0.0268(3) Uani 1 1 d . . . O4 O 0.68567(7) 0.75923(14) 0.14293(5) 0.0236(3) Uani 1 1 d . . . O1 O 0.60151(8) 1.32321(14) 0.54901(6) 0.0299(3) Uani 1 1 d . . . O5 O 1.14855(7) 0.98259(15) 0.36924(6) 0.0304(3) Uani 1 1 d . . . C5 C 0.62734(10) 0.78551(18) 0.34022(8) 0.0191(3) Uani 1 1 d . . . C10 C 0.78464(10) 0.93499(18) 0.32683(7) 0.0196(3) Uani 1 1 d . . . C9 C 0.77647(10) 0.88511(19) 0.25056(8) 0.0207(3) Uani 1 1 d . . . C11 C 0.87388(10) 1.04309(19) 0.35554(7) 0.0208(3) Uani 1 1 d . . . C12 C 0.96718(10) 0.9609(2) 0.34974(8) 0.0236(3) Uani 1 1 d . . . C4 C 0.71021(10) 0.87929(18) 0.37251(7) 0.0185(3) Uani 1 1 d . . . C6 C 0.61776(10) 0.74562(18) 0.26420(7) 0.0192(3) Uani 1 1 d . . . C17 C 0.86917(10) 1.22276(19) 0.38373(7) 0.0205(3) Uani 1 1 d . . . C8 C 0.69435(10) 0.79201(18) 0.21909(7) 0.0193(3) Uani 1 1 d . . . C16 C 0.95829(10) 1.3129(2) 0.40597(8) 0.0221(3) Uani 1 1 d . . . C3 C 0.71105(11) 0.92799(19) 0.45515(7) 0.0206(3) Uani 1 1 d . . . C19 C 0.72712(10) 1.28402(19) 0.46554(8) 0.0217(3) Uani 1 1 d . . . C13 C 1.05430(10) 1.0526(2) 0.37211(8) 0.0236(3) Uani 1 1 d . . . C2 C 0.66169(10) 1.11370(19) 0.46489(7) 0.0202(3) Uani 1 1 d . . . C18 C 0.77325(10) 1.3280(2) 0.39159(8) 0.0215(3) Uani 1 1 d . . . C15 C 1.04960(10) 1.2311(2) 0.40040(7) 0.0220(3) Uani 1 1 d . . . C1 C 0.60866(10) 1.14158(19) 0.53535(8) 0.0217(3) Uani 1 1 d . . . C7 C 0.44682(11) 0.6703(2) 0.26687(9) 0.0255(3) Uani 1 1 d . . . C20 C 0.65545(12) 1.4247(2) 0.49378(9) 0.0281(4) Uani 1 1 d . . . C14 C 1.15851(13) 0.8149(3) 0.32905(11) 0.0421(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 O3 0.0174(5) 0.0322(6) 0.0235(5) -0.0079(4) 0.0033(4) -0.0067(4) O6 0.0148(5) 0.0331(6) 0.0331(6) -0.0050(4) 0.0012(4) -0.0061(4) O2 0.0270(6) 0.0291(6) 0.0250(5) 0.0051(4) 0.0071(4) 0.0005(4) O4 0.0196(5) 0.0326(6) 0.0189(5) -0.0054(4) 0.0031(4) -0.0035(5) O1 0.0367(6) 0.0245(6) 0.0303(6) -0.0007(4) 0.0143(5) 0.0024(5) O5 0.0151(5) 0.0359(6) 0.0399(6) -0.0100(5) 0.0011(4) 0.0024(4) C5 0.0183(7) 0.0173(7) 0.0220(7) 0.0008(5) 0.0037(6) 0.0007(5) C10 0.0166(7) 0.0191(7) 0.0229(7) -0.0011(5) -0.0003(5) 0.0015(5) C9 0.0170(7) 0.0224(7) 0.0229(7) -0.0003(5) 0.0036(6) 0.0007(6) C11 0.0177(7) 0.0256(7) 0.0191(7) -0.0001(6) 0.0011(5) -0.0015(6) C12 0.0201(8) 0.0255(8) 0.0250(7) -0.0045(6) 0.0013(6) -0.0010(6) C4 0.0191(7) 0.0157(7) 0.0206(7) 0.0007(5) -0.0004(5) 0.0022(5) C6 0.0153(7) 0.0177(7) 0.0243(7) -0.0027(5) 0.0005(5) -0.0003(5) C17 0.0178(7) 0.0247(7) 0.0190(7) 0.0023(5) 0.0016(5) -0.0018(6) C8 0.0189(7) 0.0203(7) 0.0188(7) -0.0024(5) 0.0012(5) 0.0028(6) C16 0.0220(8) 0.0220(8) 0.0225(7) -0.0009(6) 0.0019(6) -0.0032(6) C3 0.0225(8) 0.0197(7) 0.0197(7) 0.0016(5) 0.0011(6) -0.0012(6) C19 0.0211(7) 0.0208(7) 0.0230(7) 0.0003(6) 0.0006(6) -0.0003(6) C13 0.0153(7) 0.0319(8) 0.0235(7) -0.0013(6) 0.0013(5) 0.0011(6) C2 0.0213(7) 0.0210(7) 0.0182(7) 0.0013(5) 0.0015(6) -0.0005(6) C18 0.0183(7) 0.0213(8) 0.0249(8) 0.0021(6) 0.0017(6) -0.0014(6) C15 0.0173(7) 0.0288(8) 0.0199(7) 0.0004(6) 0.0008(5) -0.0054(6) C1 0.0187(7) 0.0253(8) 0.0208(7) 0.0003(6) 0.0000(5) 0.0012(6) C7 0.0172(7) 0.0313(9) 0.0284(8) -0.0062(7) 0.0049(6) -0.0057(6) C20 0.0332(9) 0.0214(8) 0.0310(8) 0.0007(6) 0.0108(7) 0.0000(7) C14 0.0248(10) 0.0532(12) 0.0477(11) -0.0227(9) -0.0013(8) 0.0093(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 C6 1.3714(16) . ? O3 C7 1.4329(17) . ? O6 C15 1.3693(17) . ? O6 H6 0.87(2) . ? O2 C1 1.2053(17) . ? O4 C8 1.3723(16) . ? O4 H4 0.90(2) . ? O1 C1 1.3475(17) . ? O1 C20 1.4647(18) . ? O5 C13 1.3732(17) . ? O5 C14 1.425(2) . ? C5 C6 1.3798(19) . ? C5 C4 1.3956(19) . ? C5 H5 0.970(16) . ? C10 C4 1.3974(19) . ? C10 C9 1.4009(19) . ? C10 C11 1.4949(19) . ? C9 C8 1.3802(19) . ? C9 H9 0.976(16) . ? C11 C17 1.402(2) . ? C11 C12 1.403(2) . ? C12 C13 1.383(2) . ? C12 H12 0.972(16) . ? C4 C3 1.5115(18) . ? C6 C8 1.3954(19) . ? C17 C16 1.399(2) . ? C17 C18 1.5178(19) . ? C16 C15 1.377(2) . ? C16 H16 0.954(16) . ? C3 C2 1.5208(19) . ? C3 H3B 0.972(16) . ? C3 H3A 0.980(16) . ? C19 C20 1.518(2) . ? C19 C2 1.5199(19) . ? C19 C18 1.5303(19) . ? C19 H19 0.985(16) . ? C13 C15 1.395(2) . ? C2 C1 1.5023(19) . ? C2 H2 0.990(16) . ? C18 H18B 0.987(16) . ? C18 H18A 0.988(16) . ? C7 H7C 0.986(17) . ? C7 H7A 0.978(18) . ? C7 H7B 0.996(18) . ? C20 H20B 0.991(16) . ? C20 H20A 0.999(18) . ? C14 H14A 0.97(2) . ? C14 H14B 0.99(2) . ? C14 H14C 1.06(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 C6 O3 C7 115.56(10) . . ? C15 O6 H6 108.8(14) . . ? C8 O4 H4 108.9(13) . . ? C1 O1 C20 109.08(10) . . ? C13 O5 C14 117.24(12) . . ? C6 C5 C4 121.32(12) . . ? C6 C5 H5 119.7(9) . . ? C4 C5 H5 118.9(9) . . ? C4 C10 C9 118.69(12) . . ? C4 C10 C11 123.24(12) . . ? C9 C10 C11 118.06(12) . . ? C8 C9 C10 121.52(12) . . ? C8 C9 H9 117.6(9) . . ? C10 C9 H9 120.8(9) . . ? C17 C11 C12 119.18(12) . . ? C17 C11 C10 123.73(12) . . ? C12 C11 C10 117.00(12) . . ? C13 C12 C11 121.36(13) . . ? C13 C12 H12 120.7(9) . . ? C11 C12 H12 117.9(9) . . ? C5 C4 C10 119.32(12) . . ? C5 C4 C3 117.56(12) . . ? C10 C4 C3 122.96(12) . . ? O3 C6 C5 125.01(12) . . ? O3 C6 C8 115.36(11) . . ? C5 C6 C8 119.57(12) . . ? C16 C17 C11 118.46(13) . . ? C16 C17 C18 117.22(12) . . ? C11 C17 C18 124.33(12) . . ? O4 C8 C9 119.51(12) . . ? O4 C8 C6 120.90(12) . . ? C9 C8 C6 119.39(12) . . ? C15 C16 C17 122.05(13) . . ? C15 C16 H16 117.7(9) . . ? C17 C16 H16 120.2(9) . . ? C4 C3 C2 110.31(11) . . ? C4 C3 H3B 111.9(8) . . ? C2 C3 H3B 110.0(9) . . ? C4 C3 H3A 109.1(8) . . ? C2 C3 H3A 108.1(9) . . ? H3B C3 H3A 107.4(12) . . ? C20 C19 C2 99.69(11) . . ? C20 C19 C18 116.95(12) . . ? C2 C19 C18 115.86(11) . . ? C20 C19 H19 108.4(8) . . ? C2 C19 H19 107.3(8) . . ? C18 C19 H19 108.0(9) . . ? O5 C13 C12 125.39(13) . . ? O5 C13 C15 115.16(12) . . ? C12 C13 C15 119.45(13) . . ? C1 C2 C19 101.28(11) . . ? C1 C2 C3 117.02(11) . . ? C19 C2 C3 117.75(12) . . ? C1 C2 H2 103.2(9) . . ? C19 C2 H2 106.8(9) . . ? C3 C2 H2 109.4(9) . . ? C17 C18 C19 112.18(12) . . ? C17 C18 H18B 111.6(9) . . ? C19 C18 H18B 109.0(9) . . ? C17 C18 H18A 107.6(8) . . ? C19 C18 H18A 108.3(8) . . ? H18B C18 H18A 108.0(12) . . ? O6 C15 C16 119.40(13) . . ? O6 C15 C13 121.11(12) . . ? C16 C15 C13 119.49(12) . . ? O2 C1 O1 121.05(12) . . ? O2 C1 C2 129.81(13) . . ? O1 C1 C2 109.13(11) . . ? O3 C7 H7C 104.9(9) . . ? O3 C7 H7A 109.7(10) . . ? H7C C7 H7A 111.5(13) . . ? O3 C7 H7B 111.3(10) . . ? H7C C7 H7B 111.3(13) . . ? H7A C7 H7B 108.2(14) . . ? O1 C20 C19 104.04(11) . . ? O1 C20 H20B 107.3(9) . . ? C19 C20 H20B 111.4(9) . . ? O1 C20 H20A 106.2(9) . . ? C19 C20 H20A 114.9(10) . . ? H20B C20 H20A 112.3(13) . . ? O5 C14 H14A 109.8(11) . . ? O5 C14 H14B 104.4(11) . . ? H14A C14 H14B 109.3(16) . . ? O5 C14 H14C 110.2(11) . . ? H14A C14 H14C 111.1(16) . . ? H14B C14 H14C 111.8(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O2 0.90(2) 1.97(2) 2.7987(14) 153.8(19) 4_575 O4 H4 O3 0.90(2) 2.25(2) 2.6882(13) 110.1(16) . O6 H6 O4 0.87(2) 2.00(2) 2.8078(14) 154.0(19) 2_755 O6 H6 O5 0.87(2) 2.23(2) 2.6876(15) 112.3(16) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.209 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.038