# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Macabeo, Allan' 'Kreuzer, Andreas' 'Reiser, Oliver' _publ_contact_author_name 'Reiser, Oliver' _publ_contact_author_email Oliver.Reiser@chemie.uni-regensburg.de _publ_section_title ; Stereoselective routes to g-aryllactones and their application towards the synthesis of highly oxidised furanocembranoids ; # CIF-file generated for PhLacDiOMe Auan/Reiser #============================================================================== data_i142 _database_code_depnum_ccdc_archive 'CCDC 809453' #TrackingRef 'Compound-9c.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H16 O4' _chemical_formula_iupac ? _chemical_formula_weight 236.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 5.9224(2) _cell_length_b 11.4859(4) _cell_length_c 17.6998(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1204.01(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 5396 _cell_measurement_theta_min 3.8469 _cell_measurement_theta_max 66.3725 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.467 _exptl_crystal_size_mid 0.148 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.796 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_T_max 0.962 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5431 # number of measured reflections (redundant set) _diffrn_reflns_number 5996 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 66.57 _diffrn_reflns_theta_full 66.57 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2090 # number of observed reflections (> n sig(I)) _reflns_number_gt 2043 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0499P)^2^+0.1296P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(15) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration ad _refine_ls_number_reflns 2090 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.104 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.038 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.22413(15) 0.29507(7) 0.18356(5) 1.000 0.0255(2) . . O2 O Uani -0.06321(16) 0.26325(9) 0.10518(5) 1.000 0.0345(3) . . O3 O Uani 0.16892(15) 0.55044(8) 0.14820(5) 1.000 0.0283(3) . . O4 O Uani 0.39855(18) 0.60922(8) 0.05206(5) 1.000 0.0358(3) . . C1 C Uani 0.1235(2) 0.30136(11) 0.11505(7) 1.000 0.0266(4) . . C2 C Uani 0.2790(2) 0.35806(12) 0.05935(7) 1.000 0.0300(4) . . C3 C Uani 0.4540(2) 0.42000(11) 0.10832(7) 1.000 0.0259(4) . . C4 C Uani 0.4509(2) 0.34395(11) 0.18034(7) 1.000 0.0238(3) . . C5 C Uani 0.5037(2) 0.40433(11) 0.25407(7) 1.000 0.0240(3) . . C6 C Uani 0.7183(2) 0.45063(11) 0.26474(7) 1.000 0.0285(3) . . C7 C Uani 0.7713(2) 0.50950(12) 0.33107(8) 1.000 0.0314(4) . . C8 C Uani 0.6110(3) 0.52024(12) 0.38760(7) 1.000 0.0337(4) . . C9 C Uani 0.3986(3) 0.47235(13) 0.37786(8) 1.000 0.0376(4) . . C10 C Uani 0.3449(2) 0.41497(12) 0.31094(7) 1.000 0.0302(4) . . C11 C Uani 0.3905(2) 0.54725(12) 0.12118(7) 1.000 0.0263(3) . . C12 C Uani 0.1124(3) 0.66030(12) 0.18131(8) 1.000 0.0366(4) . . C13 C Uani 0.6090(3) 0.66504(14) 0.03878(9) 1.000 0.0445(5) . . H2A H Uiso 0.19620 0.41440 0.02730 1.000 0.0360 calc R H2B H Uiso 0.35150 0.29920 0.02650 1.000 0.0360 calc R H3 H Uiso 0.60580 0.41530 0.08380 1.000 0.0310 calc R H4 H Uiso 0.56070 0.27870 0.17340 1.000 0.0290 calc R H6 H Uiso 0.82940 0.44200 0.22650 1.000 0.0340 calc R H7 H Uiso 0.91730 0.54230 0.33760 1.000 0.0380 calc R H8 H Uiso 0.64680 0.56040 0.43300 1.000 0.0400 calc R H9 H Uiso 0.28920 0.47860 0.41690 1.000 0.0450 calc R H10 H Uiso 0.19830 0.38290 0.30430 1.000 0.0360 calc R H11 H Uiso 0.49520 0.58350 0.15870 1.000 0.0320 calc R H12A H Uiso 0.20440 0.67270 0.22660 1.000 0.0550 calc R H12B H Uiso -0.04780 0.66070 0.19520 1.000 0.0550 calc R H12C H Uiso 0.14180 0.72270 0.14480 1.000 0.0550 calc R H13A H Uiso 0.60270 0.70730 -0.00930 1.000 0.0670 calc R H13B H Uiso 0.64030 0.71990 0.07990 1.000 0.0670 calc R H13C H Uiso 0.72910 0.60640 0.03660 1.000 0.0670 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 0.0265(4) 0.0270(4) 0.0231(4) -0.0008(3) -0.0007(4) -0.0026(3) O2 0.0284(5) 0.0402(5) 0.0349(5) -0.0097(4) -0.0035(4) -0.0010(4) O3 0.0290(5) 0.0241(5) 0.0318(5) -0.0025(4) 0.0009(4) 0.0016(4) O4 0.0420(6) 0.0371(5) 0.0283(5) 0.0113(4) -0.0022(4) -0.0051(5) C1 0.0294(7) 0.0251(6) 0.0253(6) -0.0066(5) -0.0012(5) 0.0057(5) C2 0.0372(7) 0.0302(6) 0.0227(6) -0.0043(5) 0.0002(5) 0.0017(6) C3 0.0260(6) 0.0304(7) 0.0214(6) 0.0002(5) 0.0032(5) 0.0011(5) C4 0.0222(6) 0.0241(6) 0.0250(6) -0.0002(5) 0.0014(5) 0.0013(5) C5 0.0276(6) 0.0211(6) 0.0234(6) 0.0031(5) -0.0020(5) 0.0042(5) C6 0.0270(6) 0.0289(6) 0.0295(6) -0.0002(5) 0.0008(5) 0.0016(5) C7 0.0292(7) 0.0281(6) 0.0368(7) -0.0008(5) -0.0063(6) -0.0020(5) C8 0.0411(8) 0.0326(7) 0.0274(6) -0.0044(6) -0.0038(6) -0.0025(6) C9 0.0397(8) 0.0449(8) 0.0283(6) -0.0067(6) 0.0063(6) -0.0073(7) C10 0.0281(7) 0.0346(7) 0.0279(6) -0.0015(5) 0.0025(5) -0.0054(5) C11 0.0289(6) 0.0275(6) 0.0226(6) 0.0041(5) -0.0012(5) -0.0024(5) C12 0.0431(8) 0.0259(7) 0.0409(7) -0.0052(6) 0.0007(7) 0.0045(6) C13 0.0551(10) 0.0399(8) 0.0385(8) 0.0082(7) 0.0094(7) -0.0113(8) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3531(15) . . yes O1 C4 1.4568(15) . . yes O2 C1 1.2020(15) . . yes O3 C11 1.3972(15) . . yes O3 C12 1.4310(17) . . yes O4 C11 1.4162(16) . . yes O4 C13 1.421(2) . . yes C1 C2 1.4981(17) . . no C2 C3 1.5270(17) . . no C3 C4 1.5454(18) . . no C3 C11 1.5263(19) . . no C4 C5 1.5106(18) . . no C5 C6 1.3906(17) . . no C5 C10 1.3830(17) . . no C6 C7 1.3907(19) . . no C7 C8 1.385(2) . . no C8 C9 1.384(2) . . no C9 C10 1.3923(19) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C3 H3 1.0000 . . no C4 H4 1.0000 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C11 H11 1.0000 . . no C12 H12A 0.9800 . . no C12 H12B 0.9800 . . no C12 H12C 0.9800 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 110.51(9) . . . yes C11 O3 C12 112.52(11) . . . yes C11 O4 C13 113.52(11) . . . yes O1 C1 O2 121.06(11) . . . yes O1 C1 C2 110.01(10) . . . yes O2 C1 C2 128.92(11) . . . yes C1 C2 C3 104.26(10) . . . no C2 C3 C4 101.35(10) . . . no C2 C3 C11 111.32(10) . . . no C4 C3 C11 114.54(10) . . . no O1 C4 C3 105.13(9) . . . yes O1 C4 C5 109.51(10) . . . yes C3 C4 C5 116.79(10) . . . no C4 C5 C6 118.82(11) . . . no C4 C5 C10 121.91(11) . . . no C6 C5 C10 119.27(11) . . . no C5 C6 C7 120.46(11) . . . no C6 C7 C8 119.90(12) . . . no C7 C8 C9 119.86(12) . . . no C8 C9 C10 120.12(14) . . . no C5 C10 C9 120.38(12) . . . no O3 C11 O4 108.31(10) . . . yes O3 C11 C3 107.91(10) . . . yes O4 C11 C3 110.13(10) . . . yes C1 C2 H2A 111.00 . . . no C1 C2 H2B 111.00 . . . no C3 C2 H2A 111.00 . . . no C3 C2 H2B 111.00 . . . no H2A C2 H2B 109.00 . . . no C2 C3 H3 110.00 . . . no C4 C3 H3 110.00 . . . no C11 C3 H3 110.00 . . . no O1 C4 H4 108.00 . . . no C3 C4 H4 108.00 . . . no C5 C4 H4 108.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C5 C10 H10 120.00 . . . no C9 C10 H10 120.00 . . . no O3 C11 H11 110.00 . . . no O4 C11 H11 110.00 . . . no C3 C11 H11 110.00 . . . no O3 C12 H12A 109.00 . . . no O3 C12 H12B 109.00 . . . no O3 C12 H12C 109.00 . . . no H12A C12 H12B 109.00 . . . no H12A C12 H12C 110.00 . . . no H12B C12 H12C 109.00 . . . no O4 C13 H13A 109.00 . . . no O4 C13 H13B 109.00 . . . no O4 C13 H13C 109.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no 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 C4 O1 C1 O2 178.35(12) . . . . no C4 O1 C1 C2 -0.75(13) . . . . no C1 O1 C4 C5 145.08(10) . . . . no C1 O1 C4 C3 18.85(12) . . . . no C12 O3 C11 O4 -76.69(12) . . . . no C12 O3 C11 C3 164.10(10) . . . . no C13 O4 C11 C3 -93.59(12) . . . . no C13 O4 C11 O3 148.61(11) . . . . no O1 C1 C2 C3 -17.81(13) . . . . no O2 C1 C2 C3 163.19(13) . . . . no C1 C2 C3 C11 -94.90(12) . . . . no C1 C2 C3 C4 27.31(12) . . . . no C2 C3 C11 O4 -65.80(13) . . . . no C2 C3 C11 O3 52.24(13) . . . . no C2 C3 C4 C5 -149.76(10) . . . . no C4 C3 C11 O3 -62.00(13) . . . . no C2 C3 C4 O1 -28.15(11) . . . . no C11 C3 C4 C5 -29.80(15) . . . . no C4 C3 C11 O4 179.97(9) . . . . no C11 C3 C4 O1 91.80(11) . . . . no O1 C4 C5 C10 -4.28(16) . . . . no C3 C4 C5 C6 -64.86(15) . . . . no C3 C4 C5 C10 115.00(13) . . . . no O1 C4 C5 C6 175.86(11) . . . . no C4 C5 C6 C7 178.31(12) . . . . no C10 C5 C6 C7 -1.56(19) . . . . no C4 C5 C10 C9 -179.27(12) . . . . no C6 C5 C10 C9 0.6(2) . . . . no C5 C6 C7 C8 1.3(2) . . . . no C6 C7 C8 C9 0.0(2) . . . . no C7 C8 C9 C10 -1.0(2) . . . . no C8 C9 C10 C5 0.7(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O3 3.0170(12) . . no O1 C7 3.2904(16) . 4_645 no O2 C2 3.3609(16) . 3_455 no O2 C3 3.3794(16) . 1_455 no O2 C4 3.3030(15) . 1_455 no O3 C5 3.2030(15) . . no O3 C1 2.9328(16) . . no O3 O1 3.0170(12) . . no O1 H12B 2.8400 . 4_545 no O1 H10 2.3700 . . no O2 H4 2.5400 . 1_455 no O2 H7 2.8700 . 4_645 no O2 H2B 2.4900 . 3_455 no O2 H3 2.6500 . 1_455 no O3 H2A 2.6500 . . no O3 H6 2.7400 . 1_455 no O4 H2A 2.5800 . . no O4 H12C 2.5900 . . no O4 H9 2.8200 . 2_564 no O4 H13A 2.8400 . 3_465 no C1 O3 2.9328(16) . . no C1 C7 3.5405(19) . 4_645 no C1 C8 3.5917(19) . 4_645 no C2 O2 3.3609(16) . 3_555 no C3 O2 3.3794(16) . 1_655 no C4 O2 3.3030(15) . 1_655 no C5 O3 3.2030(15) . . no C6 C11 3.3848(17) . . no C7 O1 3.2904(16) . 4_655 no C7 C1 3.5405(19) . 4_655 no C7 C10 3.5841(17) . 1_655 no C8 C1 3.5917(19) . 4_655 no C10 C7 3.5841(17) . 1_455 no C11 C6 3.3848(17) . . no C1 H6 3.0900 . 1_455 no C3 H13C 2.9700 . . no C3 H6 3.0600 . . no C5 H11 2.6600 . . no C6 H12B 3.0400 . 1_655 no C6 H11 2.7600 . . no C6 H10 3.0300 . 1_655 no C7 H10 2.9600 . 1_655 no C9 H2A 3.0000 . 2_565 no C9 H13B 3.0000 . 4_645 no C9 H7 3.0500 . 1_455 no C10 H7 2.9600 . 1_455 no C10 H13B 2.9600 . 4_645 no C13 H3 2.9800 . . no H2A O3 2.6500 . . no H2A O4 2.5800 . . no H2A C9 3.0000 . 2_564 no H2A H9 2.3100 . 2_564 no H2B O2 2.4900 . 3_555 no H3 O2 2.6500 . 1_655 no H3 C13 2.9800 . . no H3 H13C 2.4600 . . no H4 O2 2.5400 . 1_655 no H4 H12A 2.5600 . 4_645 no H6 O3 2.7400 . 1_655 no H6 C1 3.0900 . 1_655 no H6 C3 3.0600 . . no H7 C9 3.0500 . 1_655 no H7 C10 2.9600 . 1_655 no H7 H10 2.5400 . 1_655 no H7 O2 2.8700 . 4_655 no H9 O4 2.8200 . 2_565 no H9 H2A 2.3100 . 2_565 no H10 O1 2.3700 . . no H10 C6 3.0300 . 1_455 no H10 C7 2.9600 . 1_455 no H10 H7 2.5400 . 1_455 no H11 C5 2.6600 . . no H11 C6 2.7600 . . no H11 H12A 2.3400 . . no H11 H13B 2.2700 . . no H11 H13C 2.5800 . . no H12A H11 2.3400 . . no H12A H4 2.5600 . 4_655 no H12B C6 3.0400 . 1_455 no H12B O1 2.8400 . 4_555 no H12C O4 2.5900 . . no H12C H13A 2.5400 . 3_465 no H13A O4 2.8400 . 3_565 no H13A H12C 2.5400 . 3_565 no H13B H11 2.2700 . . no H13B C9 3.0000 . 4_655 no H13B C10 2.9600 . 4_655 no H13C C3 2.9700 . . no H13C H3 2.4600 . . no H13C H11 2.5800 . . no 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 _geom_hbond_publ_flag C2 H2A O4 0.9900 2.5800 2.9732(17) 104.00 . yes C2 H2B O2 0.9900 2.4900 3.3609(16) 147.00 3_555 yes C4 H4 O2 1.0000 2.5400 3.3030(15) 133.00 1_655 yes C10 H10 O1 0.9500 2.3700 2.7370(15) 103.00 . yes #===END # Attachment 'Compound-14a.cif' # CIF-file generated for Macabeo DiOMeFuLac-2 #============================================================================== data_j031 _database_code_depnum_ccdc_archive 'CCDC 809454' #TrackingRef 'Compound-14a.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H20 O7' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H20 O7' _chemical_formula_iupac ? _chemical_formula_weight 288.29 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 7.8226(2) _cell_length_b 10.0497(2) _cell_length_c 9.1628(2) _cell_angle_alpha 90 _cell_angle_beta 102.925(2) _cell_angle_gamma 90 _cell_volume 702.08(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123 _cell_measurement_reflns_used 5811 _cell_measurement_theta_min 4.3962 _cell_measurement_theta_max 66.6778 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2359 _exptl_crystal_size_mid 0.1897 _exptl_crystal_size_min 0.1102 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.943 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.916 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -98.00 -18.00 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - -40.3806 125.0000 -90.0000 50 #__ type_ start__ end____ width___ exp.time_ 2 omega 25.00 116.20 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - 40.3806 37.0000 -180.0000 57 #__ type_ start__ end____ width___ exp.time_ 3 omega 21.00 115.40 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - 40.3806 37.0000 90.0000 59 #__ type_ start__ end____ width___ exp.time_ 4 omega -77.00 -16.20 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 45.0000 120.0000 38 #__ type_ start__ end____ width___ exp.time_ 5 omega -119.00 -40.60 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 125.0000 -150.0000 49 #__ type_ start__ end____ width___ exp.time_ 6 omega -144.00 -12.80 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 15.0000 90.0000 82 #__ type_ start__ end____ width___ exp.time_ 7 omega 94.00 148.40 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 45.0000 -90.0000 34 #__ type_ start__ end____ width___ exp.time_ 8 omega 104.80 170.40 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 77.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 9 omega 65.00 105.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 10 omega 73.00 161.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 45.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 11 omega 77.80 167.40 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 125.0000 -60.0000 56 #__ type_ start__ end____ width___ exp.time_ 12 omega -98.00 -18.00 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - -40.3806 125.0000 90.0000 50 #__ type_ start__ end____ width___ exp.time_ 13 omega -115.00 -11.00 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - -40.3806 -66.0000 -16.0000 65 #__ type_ start__ end____ width___ exp.time_ 14 omega 7.00 119.00 1.6000 3.0000 omega____ theta____ kappa____ phi______ frames - 40.3806 77.0000 -90.0000 70 #__ type_ start__ end____ width___ exp.time_ 15 omega -165.00 -61.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 -66.0000 -16.0000 65 #__ type_ start__ end____ width___ exp.time_ 16 omega -169.00 -57.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 -77.0000 -120.0000 70 #__ type_ start__ end____ width___ exp.time_ 17 omega 15.00 127.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 -77.0000 0.0000 70 #__ type_ start__ end____ width___ exp.time_ 18 omega 60.00 172.00 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 77.0000 90.0000 70 #__ type_ start__ end____ width___ exp.time_ 19 omega 60.00 69.60 1.6000 30.0000 omega____ theta____ kappa____ phi______ frames - 93.7786 77.0000 150.0000 6 ; _diffrn_detector_area_resol_mean 10.5431 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 6700 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.95 _diffrn_reflns_theta_max 66.79 _diffrn_reflns_theta_full 66.79 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2377 # number of observed reflections (> n sig(I)) _reflns_number_gt 2308 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0459P)^2^+0.1048P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(15) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration syn _refine_ls_number_reflns 2377 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0739 _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 _refine_diff_density_max 0.238 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.92528(17) 0.97837(13) 0.03724(13) 1.000 0.0346(4) . . O2 O Uani 0.82202(15) 0.92597(11) 0.23752(12) 1.000 0.0261(3) . . O3 O Uani 0.86698(15) 0.66420(11) 0.52019(12) 1.000 0.0266(3) . . O4 O Uani 0.48026(16) 0.80092(12) 0.06355(13) 1.000 0.0304(3) . . O5 O Uani 0.45696(15) 0.63796(12) 0.22959(13) 1.000 0.0311(4) . . O6 O Uani 1.06642(15) 0.74216(11) 0.38652(12) 1.000 0.0271(3) . . O7 O Uani 0.68930(15) 0.68963(12) 0.69216(12) 1.000 0.0312(4) . . C1 C Uani 0.8697(2) 0.89461(17) 0.10834(18) 1.000 0.0261(5) . . C2 C Uani 0.8421(2) 0.74868(16) 0.07477(19) 1.000 0.0262(5) . . C3 C Uani 0.7430(2) 0.69829(16) 0.18922(17) 1.000 0.0240(4) . . C4 C Uani 0.7738(2) 0.80806(15) 0.30923(17) 1.000 0.0235(5) . . C5 C Uani 0.9212(2) 0.77614(16) 0.44545(18) 1.000 0.0237(5) . . C6 C Uani 0.9544(2) 0.88399(16) 0.56271(18) 1.000 0.0246(5) . . C7 C Uani 0.9214(2) 0.83970(16) 0.68811(18) 1.000 0.0267(5) . . C8 C Uani 0.8607(2) 0.69777(17) 0.67162(18) 1.000 0.0273(5) . . C9 C Uani 0.5486(2) 0.67871(17) 0.12101(17) 1.000 0.0260(5) . . C10 C Uani 0.3062(3) 0.7903(2) -0.0267(2) 1.000 0.0437(6) . . C11 C Uani 0.4699(3) 0.49921(18) 0.2590(2) 1.000 0.0365(6) . . C12 C Uani 1.2262(2) 0.71962(18) 0.4950(2) 1.000 0.0311(5) . . C13 C Uani 0.6325(3) 0.5556(2) 0.7003(2) 1.000 0.0394(6) . . H2A H Uiso 0.95590 0.70210 0.08610 1.000 0.0310 calc R H2B H Uiso 0.77250 0.73490 -0.02850 1.000 0.0310 calc R H3 H Uiso 0.79580 0.61280 0.23380 1.000 0.0290 calc R H4 H Uiso 0.66250 0.82500 0.34270 1.000 0.0280 calc R H6 H Uiso 0.99370 0.97140 0.54790 1.000 0.0300 calc R H7 H Uiso 0.93410 0.89060 0.77730 1.000 0.0320 calc R H8 H Uiso 0.94110 0.63920 0.74460 1.000 0.0330 calc R H9 H Uiso 0.53290 0.61140 0.03870 1.000 0.0310 calc R H10A H Uiso 0.22830 0.75410 0.03370 1.000 0.0520 calc R H10B H Uiso 0.30640 0.73100 -0.11150 1.000 0.0520 calc R H10C H Uiso 0.26450 0.87860 -0.06400 1.000 0.0520 calc R H11A H Uiso 0.59330 0.47490 0.29610 1.000 0.0440 calc R H11B H Uiso 0.42170 0.45010 0.16650 1.000 0.0440 calc R H11C H Uiso 0.40360 0.47680 0.33460 1.000 0.0440 calc R H12A H Uiso 1.20940 0.64700 0.56170 1.000 0.0370 calc R H12B H Uiso 1.25950 0.80080 0.55380 1.000 0.0370 calc R H12C H Uiso 1.31930 0.69570 0.44380 1.000 0.0370 calc R H13A H Uiso 0.70970 0.51060 0.78490 1.000 0.0470 calc R H13B H Uiso 0.63700 0.50910 0.60720 1.000 0.0470 calc R H13C H Uiso 0.51200 0.55490 0.71430 1.000 0.0470 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 0.0438(8) 0.0340(7) 0.0277(6) 0.0022(5) 0.0115(5) -0.0093(6) O2 0.0340(6) 0.0233(6) 0.0223(6) 0.0002(4) 0.0090(5) -0.0003(4) O3 0.0367(6) 0.0216(5) 0.0240(5) -0.0008(5) 0.0124(4) -0.0010(5) O4 0.0251(6) 0.0307(6) 0.0342(6) 0.0027(5) 0.0040(5) -0.0007(5) O5 0.0318(6) 0.0326(7) 0.0326(6) -0.0011(5) 0.0150(5) -0.0059(5) O6 0.0250(6) 0.0328(6) 0.0254(6) -0.0011(5) 0.0097(5) 0.0023(5) O7 0.0312(6) 0.0336(7) 0.0313(6) -0.0005(5) 0.0124(5) -0.0006(5) C1 0.0244(8) 0.0304(9) 0.0233(8) -0.0014(7) 0.0047(6) -0.0021(6) C2 0.0264(8) 0.0288(9) 0.0256(8) -0.0029(6) 0.0107(6) -0.0018(7) C3 0.0259(8) 0.0238(8) 0.0237(7) -0.0018(6) 0.0087(6) -0.0004(6) C4 0.0258(8) 0.0219(8) 0.0252(8) -0.0003(6) 0.0110(6) 0.0002(6) C5 0.0270(8) 0.0220(8) 0.0245(8) 0.0000(6) 0.0111(6) 0.0013(6) C6 0.0249(8) 0.0218(8) 0.0272(8) 0.0001(6) 0.0059(6) 0.0000(6) C7 0.0284(9) 0.0280(9) 0.0241(8) -0.0043(7) 0.0069(6) 0.0011(6) C8 0.0312(9) 0.0302(9) 0.0227(7) 0.0013(7) 0.0108(6) 0.0008(7) C9 0.0277(8) 0.0269(8) 0.0252(8) -0.0018(7) 0.0098(6) -0.0028(6) C10 0.0284(10) 0.0488(12) 0.0512(11) 0.0064(10) 0.0035(8) -0.0008(9) C11 0.0404(11) 0.0337(9) 0.0377(10) 0.0038(8) 0.0137(8) -0.0080(8) C12 0.0275(9) 0.0328(9) 0.0332(9) -0.0030(7) 0.0074(7) 0.0013(7) C13 0.0395(10) 0.0383(10) 0.0426(11) 0.0013(8) 0.0141(8) -0.0099(8) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.204(2) . . yes O2 C1 1.355(2) . . yes O2 C4 1.4454(19) . . yes O3 C5 1.430(2) . . yes O3 C8 1.4394(19) . . yes O4 C9 1.395(2) . . yes O4 C10 1.430(3) . . yes O5 C9 1.411(2) . . yes O5 C11 1.420(2) . . yes O6 C5 1.405(2) . . yes O6 C12 1.430(2) . . yes O7 C8 1.397(2) . . yes O7 C13 1.426(2) . . yes C1 C2 1.504(2) . . no C2 C3 1.523(2) . . no C3 C4 1.538(2) . . no C3 C9 1.522(2) . . no C4 C5 1.532(2) . . no C5 C6 1.507(2) . . no C6 C7 1.311(2) . . no C7 C8 1.500(2) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C3 H3 1.0000 . . no C4 H4 1.0000 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 1.0000 . . no C9 H9 1.0000 . . no C10 H10A 0.9800 . . no C10 H10B 0.9800 . . no C10 H10C 0.9800 . . no C11 H11A 0.9800 . . no C11 H11B 0.9800 . . no C11 H11C 0.9800 . . no C12 H12A 0.9800 . . no C12 H12B 0.9800 . . no C12 H12C 0.9800 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 110.93(12) . . . yes C5 O3 C8 110.80(12) . . . yes C9 O4 C10 112.80(13) . . . yes C9 O5 C11 113.15(14) . . . yes C5 O6 C12 115.31(12) . . . yes C8 O7 C13 112.46(14) . . . yes O1 C1 O2 120.89(15) . . . yes O1 C1 C2 128.60(15) . . . yes O2 C1 C2 110.51(14) . . . yes C1 C2 C3 104.79(13) . . . no C2 C3 C4 103.37(13) . . . no C2 C3 C9 112.08(13) . . . no C4 C3 C9 111.63(13) . . . no O2 C4 C3 106.15(12) . . . yes O2 C4 C5 108.46(12) . . . yes C3 C4 C5 113.66(13) . . . no O3 C5 O6 110.18(12) . . . yes O3 C5 C4 107.77(12) . . . yes O3 C5 C6 104.28(12) . . . yes O6 C5 C4 105.29(12) . . . yes O6 C5 C6 115.06(13) . . . yes C4 C5 C6 114.11(13) . . . no C5 C6 C7 110.15(14) . . . no C6 C7 C8 110.77(14) . . . no O3 C8 O7 110.90(13) . . . yes O3 C8 C7 103.98(13) . . . yes O7 C8 C7 109.49(13) . . . yes O4 C9 O5 108.03(13) . . . yes O4 C9 C3 107.73(13) . . . yes O5 C9 C3 111.50(12) . . . yes C1 C2 H2A 111.00 . . . no C1 C2 H2B 111.00 . . . no C3 C2 H2A 111.00 . . . no C3 C2 H2B 111.00 . . . no H2A C2 H2B 109.00 . . . no C2 C3 H3 110.00 . . . no C4 C3 H3 110.00 . . . no C9 C3 H3 110.00 . . . no O2 C4 H4 109.00 . . . no C3 C4 H4 109.00 . . . no C5 C4 H4 110.00 . . . no C5 C6 H6 125.00 . . . no C7 C6 H6 125.00 . . . no C6 C7 H7 125.00 . . . no C8 C7 H7 125.00 . . . no O3 C8 H8 111.00 . . . no O7 C8 H8 111.00 . . . no C7 C8 H8 111.00 . . . no O4 C9 H9 110.00 . . . no O5 C9 H9 110.00 . . . no C3 C9 H9 110.00 . . . no O4 C10 H10A 109.00 . . . no O4 C10 H10B 110.00 . . . no O4 C10 H10C 109.00 . . . no H10A C10 H10B 109.00 . . . no H10A C10 H10C 109.00 . . . no H10B C10 H10C 109.00 . . . no O5 C11 H11A 109.00 . . . no O5 C11 H11B 109.00 . . . no O5 C11 H11C 109.00 . . . no H11A C11 H11B 109.00 . . . no H11A C11 H11C 109.00 . . . no H11B C11 H11C 109.00 . . . no O6 C12 H12A 109.00 . . . no O6 C12 H12B 109.00 . . . no O6 C12 H12C 109.00 . . . no H12A C12 H12B 109.00 . . . no H12A C12 H12C 109.00 . . . no H12B C12 H12C 109.00 . . . no O7 C13 H13A 109.00 . . . no O7 C13 H13B 109.00 . . . no O7 C13 H13C 110.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 110.00 . . . no H13B C13 H13C 109.00 . . . no 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 C4 O2 C1 O1 -175.12(15) . . . . no C4 O2 C1 C2 4.87(17) . . . . no C1 O2 C4 C5 106.11(14) . . . . no C1 O2 C4 C3 -16.39(16) . . . . no C5 O3 C8 O7 115.81(14) . . . . no C8 O3 C5 C6 1.53(16) . . . . no C8 O3 C5 C4 -120.08(13) . . . . no C5 O3 C8 C7 -1.78(16) . . . . no C8 O3 C5 O6 125.53(13) . . . . no C10 O4 C9 C3 169.57(13) . . . . no C10 O4 C9 O5 -69.85(16) . . . . no C11 O5 C9 O4 159.69(14) . . . . no C11 O5 C9 C3 -82.12(17) . . . . no C12 O6 C5 O3 -69.43(16) . . . . no C12 O6 C5 C6 48.08(18) . . . . no C12 O6 C5 C4 174.63(13) . . . . no C13 O7 C8 C7 -171.21(13) . . . . no C13 O7 C8 O3 74.61(16) . . . . no O1 C1 C2 C3 -171.28(17) . . . . no O2 C1 C2 C3 8.73(17) . . . . no C1 C2 C3 C9 102.81(15) . . . . no C1 C2 C3 C4 -17.54(16) . . . . no C4 C3 C9 O5 -61.85(17) . . . . no C2 C3 C4 O2 20.65(15) . . . . no C2 C3 C4 C5 -98.49(15) . . . . no C9 C3 C4 O2 -100.01(14) . . . . no C2 C3 C9 O5 -177.27(13) . . . . no C4 C3 C9 O4 56.52(16) . . . . no C2 C3 C9 O4 -58.90(16) . . . . no C9 C3 C4 C5 140.86(14) . . . . no C3 C4 C5 C6 179.10(13) . . . . no C3 C4 C5 O6 51.98(16) . . . . no O2 C4 C5 C6 61.30(17) . . . . no O2 C4 C5 O3 176.59(11) . . . . no O2 C4 C5 O6 -65.82(15) . . . . no C3 C4 C5 O3 -65.61(16) . . . . no O6 C5 C6 C7 -121.42(15) . . . . no C4 C5 C6 C7 116.68(16) . . . . no O3 C5 C6 C7 -0.63(18) . . . . no C5 C6 C7 C8 -0.47(19) . . . . no C6 C7 C8 O3 1.38(18) . . . . no C6 C7 C8 O7 -117.19(15) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 O4 3.0596(17) . . no O2 O6 2.7863(16) . . no O3 C6 3.307(2) . 2_746 no O4 O2 3.0596(17) . . no O4 C1 3.127(2) . . no O6 C2 3.000(2) . . no O6 C1 3.075(2) . . no O6 O2 2.7863(16) . . no O7 C11 3.418(2) . 2_656 no O1 H8 2.6000 . 2_756 no O1 H2A 2.7700 . 2_755 no O1 H7 2.5600 . 1_554 no O2 H8 2.8100 . 2_756 no O2 H6 2.9000 . . no O3 H12A 2.6300 . . no O3 H13B 2.6400 . . no O3 H6 2.3700 . 2_746 no O3 H3 2.6100 . . no O4 H11B 2.8300 . 2_655 no O4 H4 2.6500 . . no O4 H2B 2.6900 . . no O5 H4 2.5400 . . no O5 H12C 2.5100 . 1_455 no O5 H10A 2.5200 . . no O6 H2A 2.7200 . . no O6 H6 2.8500 . 2_746 no O6 H3 2.6100 . . no O7 H2B 2.5400 . 1_556 no C1 O4 3.127(2) . . no C1 O6 3.075(2) . . no C2 O6 3.000(2) . . no C6 O3 3.307(2) . 2_756 no C7 C10 3.552(3) . 1_656 no C7 C12 3.487(2) . . no C7 C11 3.583(3) . 2_656 no C8 C12 3.593(2) . . no C10 C7 3.552(3) . 1_454 no C11 O7 3.418(2) . 2_646 no C11 C7 3.583(3) . 2_646 no C12 C7 3.487(2) . . no C12 C8 3.593(2) . . no C1 H8 3.0300 . 2_756 no C1 H11B 3.0500 . 2_655 no C3 H11A 2.8100 . . no C6 H12B 2.5500 . . no C6 H12A 3.0500 . 2_756 no C7 H11C 2.8600 . 2_656 no C8 H2B 3.0000 . 1_556 no C11 H3 2.8500 . . no C11 H12C 3.0100 . 1_455 no C12 H6 3.0100 . 2_746 no C13 H2B 3.0700 . 1_556 no H2A O6 2.7200 . . no H2A H10A 2.3500 . 1_655 no H2A O1 2.7700 . 2_745 no H2B O4 2.6900 . . no H2B O7 2.5400 . 1_554 no H2B C8 3.0000 . 1_554 no H2B C13 3.0700 . 1_554 no H2B H9 2.4400 . . no H3 O3 2.6100 . . no H3 O6 2.6100 . . no H3 C11 2.8500 . . no H3 H11A 2.2700 . . no H4 O4 2.6500 . . no H4 O5 2.5400 . . no H6 O2 2.9000 . . no H6 O3 2.3700 . 2_756 no H6 O6 2.8500 . 2_756 no H6 C12 3.0100 . 2_756 no H6 H12A 2.4400 . 2_756 no H7 O1 2.5600 . 1_556 no H8 H13A 2.3200 . . no H8 O1 2.6000 . 2_746 no H8 O2 2.8100 . 2_746 no H8 C1 3.0300 . 2_746 no H9 H2B 2.4400 . . no H9 H10B 2.3200 . . no H9 H11B 2.2800 . . no H10A O5 2.5200 . . no H10A H2A 2.3500 . 1_455 no H10B H9 2.3200 . . no H11A C3 2.8100 . . no H11A H3 2.2700 . . no H11A H12B 2.3600 . 2_746 no H11B H9 2.2800 . . no H11B O4 2.8300 . 2_645 no H11B C1 3.0500 . 2_645 no H11C H12C 2.5600 . 1_455 no H11C C7 2.8600 . 2_646 no H12A O3 2.6300 . . no H12A C6 3.0500 . 2_746 no H12A H6 2.4400 . 2_746 no H12B C6 2.5500 . . no H12B H11A 2.3600 . 2_756 no H12C O5 2.5100 . 1_655 no H12C C11 3.0100 . 1_655 no H12C H11C 2.5600 . 1_655 no H13A H8 2.3200 . . no H13B O3 2.6400 . . no 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 _geom_hbond_publ_flag C2 H2B O7 0.9900 2.5400 3.492(2) 162.00 1_554 yes C4 H4 O5 1.0000 2.5400 2.965(2) 105.00 . yes C6 H6 O3 0.9500 2.3700 3.307(2) 167.00 2_756 yes C7 H7 O1 0.9500 2.5600 3.483(2) 165.00 1_556 yes C12 H12C O5 0.9800 2.5100 3.437(2) 158.00 1_655 yes #===END