data_213357 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 213357 (3694-54-01) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C16 H16 O3) (C5 H8 O4) ; _chemical_formula_sum 'C21 H24 O7' _chemical_formula_weight 388.40 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 7.2644(3) _cell_length_b 32.8801(16) _cell_length_c 7.9819(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.000(2) _cell_angle_gamma 90.00 _cell_volume 1896.07(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9967 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 32.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30177 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 32.58 _reflns_number_total 6677 _reflns_number_gt 5136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6677 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C11 C 0.76297(15) 0.05954(3) 0.38787(14) 0.0200(2) Uani 1 1 d . . . O11 O 0.65362(11) 0.08672(3) 0.44877(12) 0.02546(19) Uani 1 1 d . . . H11 H 0.571(2) 0.0737(5) 0.498(2) 0.031 Uiso 1 1 d . . . O12 O 0.73767(12) 0.02335(3) 0.39966(12) 0.0291(2) Uani 1 1 d . . . C12 C 0.91878(15) 0.07829(3) 0.30647(15) 0.0200(2) Uani 1 1 d . . . H12A H 0.9917 0.0959 0.3894 0.024 Uiso 1 1 calc R . . H12B H 0.8672 0.0957 0.2117 0.024 Uiso 1 1 calc R . . C13 C 1.04627(15) 0.04674(3) 0.24083(15) 0.0208(2) Uani 1 1 d . . . H13A H 1.0856 0.0271 0.3318 0.025 Uiso 1 1 calc R . . H13B H 0.9780 0.0315 0.1470 0.025 Uiso 1 1 calc R . . C14 C 1.21600(14) 0.06640(3) 0.17957(14) 0.0197(2) Uani 1 1 d . . . H14A H 1.1757 0.0875 0.0953 0.024 Uiso 1 1 calc R . . H14B H 1.2883 0.0800 0.2757 0.024 Uiso 1 1 calc R . . C15 C 1.33803(14) 0.03660(3) 0.10229(14) 0.0200(2) Uani 1 1 d . . . O15 O 1.48934(11) 0.05338(3) 0.05409(12) 0.02524(19) Uani 1 1 d . . . H15 H 1.551(2) 0.0345(5) 0.012(2) 0.030 Uiso 1 1 d . . . O16 O 1.30264(12) 0.00057(3) 0.08445(12) 0.0279(2) Uani 1 1 d . . . C21 C 0.25616(14) 0.07891(3) 0.67408(14) 0.0189(2) Uani 1 1 d . . . O21 O 0.38494(12) 0.05422(3) 0.61203(12) 0.02623(19) Uani 1 1 d . . . H21 H 0.352(2) 0.0293(6) 0.615(2) 0.031 Uiso 1 1 d . . . C22 C 0.09406(15) 0.06336(3) 0.72732(14) 0.0200(2) Uani 1 1 d . . . H22A H 0.0693 0.0350 0.7201 0.024 Uiso 1 1 calc R . . C23 C -0.03081(15) 0.08941(3) 0.79080(14) 0.0198(2) Uani 1 1 d . . . H23A H -0.1421 0.0787 0.8258 0.024 Uiso 1 1 calc R . . C24 C 0.00320(14) 0.13114(3) 0.80457(13) 0.01769(19) Uani 1 1 d . . . C25 C 0.16585(15) 0.14577(3) 0.74787(15) 0.0210(2) Uani 1 1 d . . . H25A H 0.1912 0.1741 0.7545 0.025 Uiso 1 1 calc R . . C26 C 0.29133(15) 0.12015(3) 0.68224(15) 0.0225(2) Uani 1 1 d . . . H26A H 0.4006 0.1308 0.6432 0.027 Uiso 1 1 calc R . . C27 C -0.12022(15) 0.15952(3) 0.87855(14) 0.0193(2) Uani 1 1 d . . . H27A H -0.0835 0.1873 0.8837 0.023 Uiso 1 1 calc R . . C31 C -0.40289(14) 0.17895(3) 1.01297(14) 0.0183(2) Uani 1 1 d . . . C32 C -0.54624(15) 0.16280(3) 1.09354(14) 0.0204(2) Uani 1 1 d . . . H32A H -0.5597 0.1341 1.1015 0.025 Uiso 1 1 calc R . . C33 C -0.67092(14) 0.18848(3) 1.16301(14) 0.0197(2) Uani 1 1 d . . . O33 O -0.80467(11) 0.16901(3) 1.23999(12) 0.02686(19) Uani 1 1 d . . . C34 C -0.65371(14) 0.23014(3) 1.15284(14) 0.0199(2) Uani 1 1 d . . . H34A H -0.7395 0.2476 1.1991 0.024 Uiso 1 1 calc R . . C35 C -0.50686(15) 0.24626(3) 1.07273(14) 0.0187(2) Uani 1 1 d . . . O35 O -0.50073(11) 0.28774(2) 1.06952(11) 0.02330(18) Uani 1 1 d . . . C36 C -0.38226(15) 0.22127(3) 1.00331(14) 0.0192(2) Uani 1 1 d . . . H36A H -0.2835 0.2326 0.9495 0.023 Uiso 1 1 calc R . . C37 C -0.27912(15) 0.15047(3) 0.93957(14) 0.0198(2) Uani 1 1 d . . . H37A H -0.3157 0.1227 0.9349 0.024 Uiso 1 1 calc R . . C38 C -0.93372(17) 0.19340(4) 1.31569(17) 0.0288(3) Uani 1 1 d . . . H38A H -1.0221 0.1759 1.3661 0.043 Uiso 1 1 calc R . . H38B H -1.0003 0.2108 1.2300 0.043 Uiso 1 1 calc R . . H38C H -0.8680 0.2104 1.4034 0.043 Uiso 1 1 calc R . . C39 C -0.34629(16) 0.30539(3) 1.00100(15) 0.0237(2) Uani 1 1 d . . . H39A H -0.3558 0.3351 1.0048 0.036 Uiso 1 1 calc R . . H39B H -0.3448 0.2965 0.8839 0.036 Uiso 1 1 calc R . . H39C H -0.2318 0.2967 1.0671 0.036 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 C11 0.0180(4) 0.0199(5) 0.0226(5) -0.0015(4) 0.0042(4) 0.0013(4) O11 0.0210(4) 0.0214(4) 0.0359(5) -0.0035(3) 0.0123(3) 0.0019(3) O12 0.0282(4) 0.0191(4) 0.0427(5) -0.0009(4) 0.0170(4) -0.0004(3) C12 0.0184(4) 0.0183(5) 0.0242(5) 0.0004(4) 0.0060(4) 0.0004(4) C13 0.0179(4) 0.0195(5) 0.0260(5) -0.0011(4) 0.0069(4) -0.0005(4) C14 0.0172(4) 0.0191(5) 0.0236(5) -0.0003(4) 0.0054(4) -0.0006(4) C15 0.0167(4) 0.0225(5) 0.0211(5) 0.0004(4) 0.0045(4) -0.0010(4) O15 0.0204(4) 0.0216(4) 0.0358(5) -0.0028(3) 0.0131(3) -0.0020(3) O16 0.0233(4) 0.0211(4) 0.0418(5) -0.0035(4) 0.0145(4) -0.0016(3) C21 0.0177(4) 0.0187(5) 0.0211(5) -0.0016(4) 0.0062(4) 0.0021(4) O21 0.0232(4) 0.0198(4) 0.0382(5) -0.0040(4) 0.0150(3) 0.0026(3) C22 0.0209(5) 0.0164(4) 0.0237(5) -0.0010(4) 0.0071(4) -0.0008(4) C23 0.0190(4) 0.0196(5) 0.0221(5) -0.0003(4) 0.0076(4) 0.0003(4) C24 0.0175(4) 0.0180(5) 0.0181(5) -0.0001(4) 0.0041(4) 0.0019(4) C25 0.0207(5) 0.0166(5) 0.0268(5) -0.0006(4) 0.0078(4) -0.0009(4) C26 0.0187(4) 0.0199(5) 0.0305(6) -0.0017(4) 0.0098(4) -0.0018(4) C27 0.0208(5) 0.0175(5) 0.0203(5) -0.0004(4) 0.0051(4) 0.0019(4) C31 0.0174(4) 0.0190(5) 0.0191(5) -0.0013(4) 0.0044(4) 0.0013(4) C32 0.0193(5) 0.0182(5) 0.0246(5) -0.0013(4) 0.0064(4) 0.0000(4) C33 0.0164(4) 0.0218(5) 0.0217(5) -0.0011(4) 0.0059(4) -0.0009(4) O33 0.0222(4) 0.0229(4) 0.0384(5) -0.0027(3) 0.0168(3) -0.0026(3) C34 0.0184(4) 0.0207(5) 0.0212(5) -0.0011(4) 0.0056(4) 0.0022(4) C35 0.0199(4) 0.0180(5) 0.0184(5) 0.0009(4) 0.0036(4) 0.0026(4) O35 0.0262(4) 0.0171(4) 0.0287(4) 0.0013(3) 0.0130(3) 0.0023(3) C36 0.0191(4) 0.0193(5) 0.0201(5) 0.0007(4) 0.0067(4) 0.0019(4) C37 0.0203(5) 0.0184(5) 0.0216(5) -0.0009(4) 0.0059(4) 0.0022(4) C38 0.0231(5) 0.0285(6) 0.0375(7) -0.0032(5) 0.0161(5) 0.0004(5) C39 0.0262(5) 0.0196(5) 0.0267(6) 0.0005(4) 0.0093(4) -0.0020(4) _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 C11 O12 1.2091(14) . ? C11 O11 1.3216(13) . ? C11 C12 1.4956(15) . ? O11 H11 0.867(17) . ? C12 C13 1.5198(15) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5177(14) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.4969(15) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O16 1.2174(14) . ? C15 O15 1.3225(12) . ? O15 H15 0.858(17) . ? C21 O21 1.3697(12) . ? C21 C26 1.3804(15) . ? C21 C22 1.3904(14) . ? O21 H21 0.854(18) . ? C22 C23 1.3819(14) . ? C22 H22A 0.9500 . ? C23 C24 1.3965(15) . ? C23 H23A 0.9500 . ? C24 C25 1.3943(14) . ? C24 C27 1.4608(14) . ? C25 C26 1.3837(14) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 C37 1.3326(14) . ? C27 H27A 0.9500 . ? C31 C32 1.3856(14) . ? C31 C36 1.4027(15) . ? C31 C37 1.4624(14) . ? C32 C33 1.3949(14) . ? C32 H32A 0.9500 . ? C33 O33 1.3625(13) . ? C33 C34 1.3787(16) . ? O33 C38 1.4162(13) . ? C34 C35 1.4038(14) . ? C34 H34A 0.9500 . ? C35 O35 1.3649(13) . ? C35 C36 1.3806(14) . ? O35 C39 1.4221(13) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 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 O12 C11 O11 122.33(10) . . ? O12 C11 C12 124.57(10) . . ? O11 C11 C12 113.10(9) . . ? C11 O11 H11 107.8(11) . . ? C11 C12 C13 112.62(9) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 111.42(9) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 112.95(9) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? O16 C15 O15 122.94(10) . . ? O16 C15 C14 123.93(9) . . ? O15 C15 C14 113.12(9) . . ? C15 O15 H15 107.4(11) . . ? O21 C21 C26 117.99(9) . . ? O21 C21 C22 121.66(10) . . ? C26 C21 C22 120.35(9) . . ? C21 O21 H21 110.7(11) . . ? C23 C22 C21 119.57(10) . . ? C23 C22 H22A 120.2 . . ? C21 C22 H22A 120.2 . . ? C22 C23 C24 121.36(10) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? C25 C24 C23 117.54(9) . . ? C25 C24 C27 119.18(10) . . ? C23 C24 C27 123.26(9) . . ? C26 C25 C24 121.80(10) . . ? C26 C25 H25A 119.1 . . ? C24 C25 H25A 119.1 . . ? C21 C26 C25 119.34(9) . . ? C21 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C37 C27 C24 126.64(10) . . ? C37 C27 H27A 116.7 . . ? C24 C27 H27A 116.7 . . ? C32 C31 C36 119.70(9) . . ? C32 C31 C37 117.64(10) . . ? C36 C31 C37 122.65(9) . . ? C31 C32 C33 120.22(10) . . ? C31 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? O33 C33 C34 124.53(9) . . ? O33 C33 C32 114.71(10) . . ? C34 C33 C32 120.76(10) . . ? C33 O33 C38 117.47(9) . . ? C33 C34 C35 118.68(9) . . ? C33 C34 H34A 120.7 . . ? C35 C34 H34A 120.7 . . ? O35 C35 C36 124.27(9) . . ? O35 C35 C34 114.44(9) . . ? C36 C35 C34 121.29(10) . . ? C35 O35 C39 116.32(8) . . ? C35 C36 C31 119.35(9) . . ? C35 C36 H36A 120.3 . . ? C31 C36 H36A 120.3 . . ? C27 C37 C31 126.57(10) . . ? C27 C37 H37A 116.7 . . ? C31 C37 H37A 116.7 . . ? O33 C38 H38A 109.5 . . ? O33 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O33 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O35 C39 H39A 109.5 . . ? O35 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O35 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 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 O12 C11 C12 C13 -0.81(17) . . . . ? O11 C11 C12 C13 178.57(10) . . . . ? C11 C12 C13 C14 -172.64(10) . . . . ? C12 C13 C14 C15 -175.77(9) . . . . ? C13 C14 C15 O16 2.48(17) . . . . ? C13 C14 C15 O15 -177.78(10) . . . . ? O21 C21 C22 C23 179.27(11) . . . . ? C26 C21 C22 C23 -0.90(17) . . . . ? C21 C22 C23 C24 -0.75(17) . . . . ? C22 C23 C24 C25 1.60(17) . . . . ? C22 C23 C24 C27 -176.85(11) . . . . ? C23 C24 C25 C26 -0.86(17) . . . . ? C27 C24 C25 C26 177.65(11) . . . . ? O21 C21 C26 C25 -178.55(11) . . . . ? C22 C21 C26 C25 1.61(18) . . . . ? C24 C25 C26 C21 -0.72(18) . . . . ? C25 C24 C27 C37 -179.45(11) . . . . ? C23 C24 C27 C37 -1.03(18) . . . . ? C36 C31 C32 C33 0.78(17) . . . . ? C37 C31 C32 C33 -178.71(10) . . . . ? C31 C32 C33 O33 -179.48(10) . . . . ? C31 C32 C33 C34 -0.04(18) . . . . ? C34 C33 O33 C38 -0.50(17) . . . . ? C32 C33 O33 C38 178.92(11) . . . . ? O33 C33 C34 C35 178.69(10) . . . . ? C32 C33 C34 C35 -0.69(17) . . . . ? C33 C34 C35 O35 -179.72(10) . . . . ? C33 C34 C35 C36 0.69(17) . . . . ? C36 C35 O35 C39 -5.04(16) . . . . ? C34 C35 O35 C39 175.39(10) . . . . ? O35 C35 C36 C31 -179.51(10) . . . . ? C34 C35 C36 C31 0.03(17) . . . . ? C32 C31 C36 C35 -0.77(17) . . . . ? C37 C31 C36 C35 178.70(10) . . . . ? C24 C27 C37 C31 -179.73(11) . . . . ? C32 C31 C37 C27 -169.94(11) . . . . ? C36 C31 C37 C27 10.59(18) . . . . ? 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 O11 H11 O21 0.867(17) 1.821(17) 2.6798(12) 170.9(16) . O15 H15 O16 0.858(17) 1.792(17) 2.6463(12) 173.5(16) 3_855 O21 H21 O12 0.854(18) 1.850(19) 2.7001(12) 173.7(16) 3_656 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.570 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.062