data_x1210006 _audit_creation_date 2012-10-16 _audit_creation_method ; Olex2 1.2-beta (compiled Oct 2 2012 15:58:45, GUI svn.r4355) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H16 O8' _chemical_formula_sum 'C16 H16 O8' _chemical_formula_weight 336.29 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'orthorhombic' _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 8.0332(6) _cell_length_b 10.8528(8) _cell_length_c 17.7547(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1547.9(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9965 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 70.10 _cell_measurement_theta_min 4.78 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_T_max 0.8898 _exptl_absorpt_correction_T_min 0.8070 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS was used for absorption correction. wR2(int) was 0.0514 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.9069. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'block' _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.397 _exptl_crystal_size_mid 0.198 _exptl_crystal_size_min 0.139 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0121 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17945 _diffrn_reflns_theta_full 70.09 _diffrn_reflns_theta_max 70.09 _diffrn_reflns_theta_min 4.78 _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'CuK\a' _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 2900 _reflns_number_total 2928 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.169 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(11) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 2928 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0236 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.0608 _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. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.88278(10) 0.69397(8) 0.31786(5) 0.02351(19) Uani 1 1 d . . . O2 O 0.73993(10) 0.86882(7) 0.35457(4) 0.02072(18) Uani 1 1 d . . . O3 O 0.44021(11) 0.25406(8) 0.52345(5) 0.02513(19) Uani 1 1 d . . . O4 O 0.21945(11) 0.43789(9) 0.48885(5) 0.0310(2) Uani 1 1 d . . . O5 O 0.34941(11) 0.46371(8) 0.37728(5) 0.02245(18) Uani 1 1 d . . . O6 O 0.44831(11) 0.22971(8) 0.64781(5) 0.02644(19) Uani 1 1 d . . . O7 O 0.81485(11) 0.35399(8) 0.64755(5) 0.02499(19) Uani 1 1 d . . . O8 O 0.69700(11) 0.53195(8) 0.68518(5) 0.02224(18) Uani 1 1 d . . . C1 C 0.76256(14) 0.55548(11) 0.41377(6) 0.0191(2) Uani 1 1 d . . . H1 H 0.8233(18) 0.4842(14) 0.4002(8) 0.016(3) Uiso 1 1 d . . . C2 C 0.77874(14) 0.66620(10) 0.37702(6) 0.0183(2) Uani 1 1 d . . . C3 C 0.82791(16) 0.81294(11) 0.29238(7) 0.0212(2) Uani 1 1 d . . . H3A H 0.9214(19) 0.8614(13) 0.2810(8) 0.018(3) Uiso 1 1 d . . . H3B H 0.7543(18) 0.8047(12) 0.2498(8) 0.016(3) Uiso 1 1 d . . . C4 C 0.69129(14) 0.77019(10) 0.39842(6) 0.0180(2) Uani 1 1 d . . . C5 C 0.58119(15) 0.76885(11) 0.45782(6) 0.0209(2) Uani 1 1 d . . . H5 H 0.5209(18) 0.8396(14) 0.4720(8) 0.021(3) Uiso 1 1 d . . . C6 C 0.56039(14) 0.65551(11) 0.49475(6) 0.0205(2) Uani 1 1 d . . . H6 H 0.4807(19) 0.6488(14) 0.5364(9) 0.025(4) Uiso 1 1 d . . . C7 C 0.64716(14) 0.55060(10) 0.47339(6) 0.0175(2) Uani 1 1 d . . . C8 C 0.61917(14) 0.42533(11) 0.50844(6) 0.0187(2) Uani 1 1 d . . . H8 H 0.7220(17) 0.3786(12) 0.5049(8) 0.015(3) Uiso 1 1 d . . . C9 C 0.48718(16) 0.34441(11) 0.46811(7) 0.0217(2) Uani 1 1 d . . . H9 H 0.5296(17) 0.3025(13) 0.4250(8) 0.016(3) Uiso 1 1 d . . . C10 C 0.47831(15) 0.29180(11) 0.59378(7) 0.0209(2) Uani 1 1 d . . . C11 C 0.55900(14) 0.41874(10) 0.59052(6) 0.0183(2) Uani 1 1 d . . . H11 H 0.4764(16) 0.4789(12) 0.6015(7) 0.007(3) Uiso 1 1 d . . . C12 C 0.33367(16) 0.41873(11) 0.44668(7) 0.0225(2) Uani 1 1 d . . . C13 C 0.21911(16) 0.54998(12) 0.35372(7) 0.0257(3) Uani 1 1 d . . . H13A H 0.117(2) 0.5042(14) 0.3431(8) 0.022(3) Uiso 1 1 d . . . H13B H 0.199(2) 0.6053(15) 0.3951(10) 0.035(4) Uiso 1 1 d . . . C14 C 0.28097(17) 0.61475(12) 0.28476(8) 0.0287(3) Uani 1 1 d . . . H14A H 0.381(2) 0.6619(15) 0.2962(9) 0.028(4) Uiso 1 1 d . . . H14B H 0.196(2) 0.6724(17) 0.2698(10) 0.041(5) Uiso 1 1 d . . . H14C H 0.304(2) 0.5566(16) 0.2405(10) 0.039(4) Uiso 1 1 d . . . C15 C 0.70440(14) 0.42846(10) 0.64454(6) 0.0187(2) Uani 1 1 d . . . C16 C 0.83979(17) 0.55354(12) 0.73378(7) 0.0265(3) Uani 1 1 d . . . H16A H 0.808(2) 0.6220(16) 0.7660(10) 0.038(4) Uiso 1 1 d . . . H16B H 0.858(2) 0.4792(15) 0.7638(9) 0.026(4) Uiso 1 1 d . . . H16C H 0.938(2) 0.5729(15) 0.7030(9) 0.028(4) Uiso 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 0.0244(4) 0.0218(4) 0.0243(4) 0.0047(3) 0.0075(3) 0.0037(3) O2 0.0252(4) 0.0170(4) 0.0200(4) 0.0004(3) 0.0019(3) -0.0009(3) O3 0.0323(5) 0.0195(4) 0.0235(4) 0.0027(3) -0.0029(4) -0.0070(4) O4 0.0246(4) 0.0412(5) 0.0272(4) 0.0018(4) 0.0027(4) -0.0002(4) O5 0.0233(4) 0.0218(4) 0.0222(4) -0.0002(3) -0.0016(3) 0.0034(3) O6 0.0301(5) 0.0240(4) 0.0253(4) 0.0044(3) 0.0036(4) -0.0043(4) O7 0.0244(4) 0.0251(4) 0.0255(4) 0.0001(3) -0.0013(3) 0.0058(3) O8 0.0227(4) 0.0199(4) 0.0242(4) -0.0016(3) -0.0042(3) 0.0006(3) C1 0.0171(5) 0.0197(5) 0.0206(5) -0.0020(4) -0.0001(4) 0.0036(4) C2 0.0149(5) 0.0223(6) 0.0177(5) -0.0015(4) -0.0006(4) 0.0001(4) C3 0.0243(6) 0.0198(5) 0.0195(5) 0.0014(4) 0.0027(5) -0.0006(5) C4 0.0194(5) 0.0161(5) 0.0184(5) -0.0003(4) -0.0047(4) -0.0014(4) C5 0.0230(6) 0.0176(5) 0.0221(6) -0.0029(4) 0.0022(5) 0.0028(5) C6 0.0203(5) 0.0222(6) 0.0191(5) -0.0016(4) 0.0034(5) -0.0012(5) C7 0.0162(5) 0.0191(5) 0.0173(5) 0.0002(4) -0.0018(4) -0.0004(4) C8 0.0187(5) 0.0179(5) 0.0195(5) -0.0003(4) 0.0008(4) 0.0026(4) C9 0.0281(6) 0.0171(5) 0.0201(5) 0.0000(5) 0.0013(5) -0.0013(5) C10 0.0193(5) 0.0190(6) 0.0244(6) 0.0001(4) 0.0013(4) -0.0004(4) C11 0.0183(5) 0.0165(5) 0.0200(5) 0.0013(4) 0.0025(4) 0.0008(5) C12 0.0242(6) 0.0213(6) 0.0221(5) -0.0031(5) -0.0030(5) -0.0050(5) C13 0.0222(6) 0.0278(6) 0.0270(6) -0.0005(5) -0.0009(5) 0.0059(5) C14 0.0249(6) 0.0265(6) 0.0348(7) 0.0060(5) -0.0018(5) 0.0028(6) C15 0.0208(5) 0.0171(5) 0.0182(5) 0.0040(4) 0.0025(4) -0.0021(5) C16 0.0271(6) 0.0261(6) 0.0264(6) 0.0003(5) -0.0068(5) -0.0045(5) _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 1.3758(14) . ? O1 C3 1.4374(14) . ? O2 C3 1.4445(14) . ? O2 C4 1.3801(14) . ? O3 C9 1.4386(14) . ? O3 C10 1.3492(15) . ? O4 C12 1.2024(16) . ? O5 C12 1.3315(15) . ? O5 C13 1.4654(15) . ? O6 C10 1.1969(15) . ? O7 C15 1.2014(15) . ? O8 C15 1.3364(14) . ? O8 C16 1.4543(15) . ? C1 H1 0.946(15) . ? C1 C2 1.3735(16) . ? C1 C7 1.4080(16) . ? C2 C4 1.3826(16) . ? C3 H3A 0.939(16) . ? C3 H3B 0.964(14) . ? C4 C5 1.3764(16) . ? C5 H5 0.942(15) . ? C5 C6 1.4040(16) . ? C6 H6 0.980(16) . ? C6 C7 1.3877(16) . ? C7 C8 1.5120(15) . ? C8 H8 0.971(14) . ? C8 C9 1.5519(16) . ? C8 C11 1.5370(15) . ? C9 H9 0.954(14) . ? C9 C12 1.5219(17) . ? C10 C11 1.5236(16) . ? C11 H11 0.951(13) . ? C11 C15 1.5151(16) . ? C13 H13A 0.976(16) . ? C13 H13B 0.963(17) . ? C13 C14 1.4967(19) . ? C14 H14A 0.974(17) . ? C14 H14B 0.964(19) . ? C14 H14C 1.025(18) . ? C16 H16A 0.973(18) . ? C16 H16B 0.978(16) . ? C16 H16C 0.980(17) . ? 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 C3 104.52(9) . . ? C4 O2 C3 104.13(8) . . ? C10 O3 C9 111.45(9) . . ? C12 O5 C13 115.51(10) . . ? C15 O8 C16 114.88(10) . . ? C2 C1 H1 123.1(8) . . ? C2 C1 C7 116.89(10) . . ? C7 C1 H1 120.0(8) . . ? O1 C2 C4 109.86(10) . . ? C1 C2 O1 127.72(10) . . ? C1 C2 C4 122.38(10) . . ? O1 C3 O2 106.66(9) . . ? O1 C3 H3A 109.0(9) . . ? O1 C3 H3B 110.6(8) . . ? O2 C3 H3A 108.7(9) . . ? O2 C3 H3B 109.8(8) . . ? H3A C3 H3B 112.0(11) . . ? O2 C4 C2 109.53(9) . . ? C5 C4 O2 128.49(10) . . ? C5 C4 C2 121.90(10) . . ? C4 C5 H5 121.8(9) . . ? C4 C5 C6 116.33(10) . . ? C6 C5 H5 121.9(9) . . ? C5 C6 H6 119.6(9) . . ? C7 C6 C5 122.10(11) . . ? C7 C6 H6 118.3(9) . . ? C1 C7 C8 116.17(10) . . ? C6 C7 C1 120.35(10) . . ? C6 C7 C8 123.40(10) . . ? C7 C8 H8 108.4(8) . . ? C7 C8 C9 114.87(9) . . ? C7 C8 C11 118.61(9) . . ? C9 C8 H8 104.8(8) . . ? C11 C8 H8 107.8(8) . . ? C11 C8 C9 101.32(9) . . ? O3 C9 C8 104.46(9) . . ? O3 C9 H9 108.5(8) . . ? O3 C9 C12 108.63(10) . . ? C8 C9 H9 113.4(9) . . ? C12 C9 C8 111.66(9) . . ? C12 C9 H9 110.0(8) . . ? O3 C10 C11 109.62(9) . . ? O6 C10 O3 121.68(11) . . ? O6 C10 C11 128.70(11) . . ? C8 C11 H11 112.5(7) . . ? C10 C11 C8 102.23(9) . . ? C10 C11 H11 108.4(8) . . ? C15 C11 C8 110.77(9) . . ? C15 C11 C10 111.52(9) . . ? C15 C11 H11 111.1(7) . . ? O4 C12 O5 125.83(12) . . ? O4 C12 C9 123.67(11) . . ? O5 C12 C9 110.41(10) . . ? O5 C13 H13A 109.2(9) . . ? O5 C13 H13B 107.5(10) . . ? O5 C13 C14 107.24(10) . . ? H13A C13 H13B 108.9(14) . . ? C14 C13 H13A 111.1(9) . . ? C14 C13 H13B 112.8(10) . . ? C13 C14 H14A 110.4(9) . . ? C13 C14 H14B 107.1(11) . . ? C13 C14 H14C 113.5(10) . . ? H14A C14 H14B 107.6(14) . . ? H14A C14 H14C 109.4(14) . . ? H14B C14 H14C 108.6(14) . . ? O7 C15 O8 125.05(11) . . ? O7 C15 C11 123.42(10) . . ? O8 C15 C11 111.47(10) . . ? O8 C16 H16A 105.4(11) . . ? O8 C16 H16B 108.0(10) . . ? O8 C16 H16C 109.6(9) . . ? H16A C16 H16B 110.4(13) . . ? H16A C16 H16C 112.1(14) . . ? H16B C16 H16C 111.2(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 O1 C2 C4 O2 -1.45(12) . . . . ? O1 C2 C4 C5 -178.30(10) . . . . ? O2 C4 C5 C6 -177.24(11) . . . . ? O3 C9 C12 O4 29.75(15) . . . . ? O3 C9 C12 O5 -153.62(9) . . . . ? O3 C10 C11 C8 -20.35(12) . . . . ? O3 C10 C11 C15 -138.74(10) . . . . ? O6 C10 C11 C8 160.06(12) . . . . ? O6 C10 C11 C15 41.67(16) . . . . ? C1 C2 C4 O2 176.36(10) . . . . ? C1 C2 C4 C5 -0.49(17) . . . . ? C1 C7 C8 C9 -85.68(12) . . . . ? C1 C7 C8 C11 154.36(11) . . . . ? C2 O1 C3 O2 21.85(11) . . . . ? C2 C1 C7 C6 -2.48(16) . . . . ? C2 C1 C7 C8 174.50(10) . . . . ? C2 C4 C5 C6 -1.03(17) . . . . ? C3 O1 C2 C1 169.51(11) . . . . ? C3 O1 C2 C4 -12.83(12) . . . . ? C3 O2 C4 C2 14.96(12) . . . . ? C3 O2 C4 C5 -168.45(12) . . . . ? C4 O2 C3 O1 -22.64(11) . . . . ? C4 C5 C6 C7 0.74(18) . . . . ? C5 C6 C7 C1 1.04(18) . . . . ? C5 C6 C7 C8 -175.71(11) . . . . ? C6 C7 C8 C9 91.19(13) . . . . ? C6 C7 C8 C11 -28.76(16) . . . . ? C7 C1 C2 O1 179.63(10) . . . . ? C7 C1 C2 C4 2.24(16) . . . . ? C7 C8 C9 O3 -160.48(9) . . . . ? C7 C8 C9 C12 -43.26(13) . . . . ? C7 C8 C11 C10 157.12(10) . . . . ? C7 C8 C11 C15 -83.96(12) . . . . ? C8 C9 C12 O4 -84.92(14) . . . . ? C8 C9 C12 O5 91.71(11) . . . . ? C8 C11 C15 O7 -63.02(14) . . . . ? C8 C11 C15 O8 114.22(10) . . . . ? C9 O3 C10 O6 179.64(11) . . . . ? C9 O3 C10 C11 0.01(13) . . . . ? C9 C8 C11 C10 30.41(11) . . . . ? C9 C8 C11 C15 149.34(9) . . . . ? C10 O3 C9 C8 20.32(12) . . . . ? C10 O3 C9 C12 -98.96(11) . . . . ? C10 C11 C15 O7 50.13(14) . . . . ? C10 C11 C15 O8 -132.63(10) . . . . ? C11 C8 C9 O3 -31.35(11) . . . . ? C11 C8 C9 C12 85.87(11) . . . . ? C12 O5 C13 C14 165.15(10) . . . . ? C13 O5 C12 O4 4.03(17) . . . . ? C13 O5 C12 C9 -172.51(9) . . . . ? C16 O8 C15 O7 2.31(16) . . . . ? C16 O8 C15 C11 -174.88(9) . . . . ?