# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_l246 _database_code_depnum_ccdc_archive 'CCDC 909409' #TrackingRef '15206_web_deposit_cif_file_0_SabineAmslinger_1352139086.Compound_20.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 O5' # 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 'C18 H18 O5' _chemical_formula_iupac ? _chemical_formula_weight 314.32 _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 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 17.9253(7) _cell_length_b 5.36599(19) _cell_length_c 15.7715(5) _cell_angle_alpha 90 _cell_angle_beta 98.798(3) _cell_angle_gamma 90 _cell_volume 1499.16(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123.01(10) _cell_measurement_reflns_used 6233 _cell_measurement_theta_min 3.4755 _cell_measurement_theta_max 73.4147 _cell_special_details ; ; _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.2913 _exptl_crystal_size_mid 0.1360 _exptl_crystal_size_min 0.0431 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.840 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 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 0.832 _exptl_absorpt_correction_T_max 0.965 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123.01(10) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3546 # number of measured reflections (redundant set) _diffrn_reflns_number 11609 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 73.58 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2974 # number of observed reflections (> n sig(I)) _reflns_number_gt 2642 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0508P)^2^+0.4987P] 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 ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2974 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0916 _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 _refine_diff_density_max 0.203 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.050 #=============================================================================== # 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 -0.09479(4) 0.44706(16) 0.38343(5) 1.000 0.0208(2) . . O2 O Uani 0.16121(5) 0.17446(16) 0.44162(6) 1.000 0.0258(3) . . O3 O Uani 0.25910(5) 0.42773(17) 0.37992(6) 1.000 0.0290(3) . . O4 O Uani 0.50342(5) 1.06408(17) 0.11471(6) 1.000 0.0250(3) . . O5 O Uani 0.42104(5) 1.41626(16) 0.03915(6) 1.000 0.0241(3) . . C1 C Uani -0.02012(6) 0.4670(2) 0.37828(7) 1.000 0.0170(3) . . C2 C Uani 0.03481(6) 0.3014(2) 0.41488(7) 1.000 0.0185(3) . . C3 C Uani 0.10988(6) 0.3384(2) 0.40399(7) 1.000 0.0182(3) . . C4 C Uani 0.13064(6) 0.5406(2) 0.35503(7) 1.000 0.0170(3) . . C5 C Uani 0.07303(6) 0.7056(2) 0.32007(7) 1.000 0.0176(3) . . C6 C Uani -0.00076(6) 0.6725(2) 0.33092(7) 1.000 0.0184(3) . . C7 C Uani -0.11913(7) 0.2386(2) 0.42924(8) 1.000 0.0231(3) . . C8 C Uani 0.20972(7) 0.5714(2) 0.34300(8) 1.000 0.0195(3) . . C9 C Uani 0.23022(7) 0.7673(2) 0.28562(8) 1.000 0.0202(3) . . C10 C Uani 0.29943(7) 0.7758(2) 0.26389(8) 1.000 0.0203(3) . . C11 C Uani 0.32746(7) 0.9502(2) 0.20535(7) 1.000 0.0192(3) . . C12 C Uani 0.40217(7) 0.9218(2) 0.18958(8) 1.000 0.0199(3) . . C13 C Uani 0.43199(6) 1.0788(2) 0.13393(8) 1.000 0.0193(3) . . C14 C Uani 0.38691(7) 1.2711(2) 0.09218(7) 1.000 0.0194(3) . . C15 C Uani 0.31309(7) 1.2994(2) 0.10736(8) 1.000 0.0218(3) . . C16 C Uani 0.28361(7) 1.1406(2) 0.16357(8) 1.000 0.0215(3) . . C17 C Uani 0.54639(7) 0.8478(2) 0.14377(9) 1.000 0.0247(4) . . C18 C Uani 0.37526(8) 1.5936(2) -0.01316(8) 1.000 0.0264(4) . . H2 H Uiso 0.02150 0.16350 0.44720 1.000 0.0220 calc R H2A H Uiso 0.20420 0.21400 0.43100 1.000 0.0310 calc R H5 H Uiso 0.08570 0.84470 0.28780 1.000 0.0210 calc R H6 H Uiso -0.03840 0.78730 0.30670 1.000 0.0220 calc R H7A H Uiso -0.09380 0.24270 0.48890 1.000 0.0280 calc R H7B H Uiso -0.10630 0.08330 0.40210 1.000 0.0280 calc R H7C H Uiso -0.17390 0.24740 0.42810 1.000 0.0280 calc R H9 H Uiso 0.19390 0.88920 0.26370 1.000 0.0240 calc R H10 H Uiso 0.33430 0.65420 0.28960 1.000 0.0240 calc R H12 H Uiso 0.43260 0.79240 0.21770 1.000 0.0240 calc R H15 H Uiso 0.28250 1.42830 0.07910 1.000 0.0260 calc R H16 H Uiso 0.23310 1.16230 0.17350 1.000 0.0260 calc R H17A H Uiso 0.52030 0.69860 0.11860 1.000 0.0300 calc R H17B H Uiso 0.55190 0.83810 0.20650 1.000 0.0300 calc R H17C H Uiso 0.59640 0.85840 0.12610 1.000 0.0300 calc R H18A H Uiso 0.35270 1.70980 0.02360 1.000 0.0320 calc R H18B H Uiso 0.33520 1.50610 -0.05090 1.000 0.0320 calc R H18C H Uiso 0.40660 1.68640 -0.04800 1.000 0.0320 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 0.0161(4) 0.0234(4) 0.0233(4) 0.0040(3) 0.0044(3) -0.0017(3) O2 0.0180(4) 0.0248(5) 0.0348(5) 0.0129(4) 0.0051(4) 0.0028(3) O3 0.0184(4) 0.0333(5) 0.0360(5) 0.0161(4) 0.0069(4) 0.0039(4) O4 0.0183(4) 0.0286(5) 0.0297(5) 0.0064(4) 0.0086(4) -0.0010(3) O5 0.0240(4) 0.0258(5) 0.0228(4) 0.0069(3) 0.0046(4) -0.0053(3) C1 0.0162(5) 0.0191(5) 0.0159(5) -0.0034(4) 0.0033(4) -0.0030(4) C2 0.0209(6) 0.0171(5) 0.0179(6) 0.0020(4) 0.0047(4) -0.0027(4) C3 0.0203(6) 0.0169(5) 0.0170(5) 0.0008(4) 0.0018(4) 0.0008(4) C4 0.0185(6) 0.0167(5) 0.0158(5) 0.0000(4) 0.0031(4) -0.0016(4) C5 0.0204(6) 0.0166(5) 0.0161(5) 0.0012(4) 0.0035(4) -0.0016(4) C6 0.0196(6) 0.0180(5) 0.0172(5) 0.0011(4) 0.0015(4) 0.0016(4) C7 0.0206(6) 0.0229(6) 0.0267(6) 0.0022(5) 0.0066(5) -0.0047(5) C8 0.0194(6) 0.0207(6) 0.0186(6) 0.0018(4) 0.0032(4) -0.0002(4) C9 0.0196(6) 0.0204(6) 0.0209(6) 0.0035(5) 0.0041(5) -0.0005(4) C10 0.0197(6) 0.0209(6) 0.0201(6) 0.0019(5) 0.0027(5) -0.0005(4) C11 0.0200(6) 0.0199(6) 0.0180(6) -0.0014(5) 0.0036(4) -0.0033(4) C12 0.0193(6) 0.0202(6) 0.0201(6) 0.0007(4) 0.0024(5) -0.0015(4) C13 0.0170(5) 0.0221(6) 0.0191(6) -0.0024(4) 0.0037(4) -0.0040(4) C14 0.0227(6) 0.0194(5) 0.0162(5) -0.0005(4) 0.0037(4) -0.0067(4) C15 0.0227(6) 0.0202(6) 0.0221(6) 0.0022(5) 0.0024(5) -0.0005(5) C16 0.0193(6) 0.0229(6) 0.0232(6) 0.0011(5) 0.0064(5) -0.0016(5) C17 0.0188(6) 0.0247(6) 0.0312(7) -0.0001(5) 0.0058(5) -0.0007(5) C18 0.0304(7) 0.0260(6) 0.0224(6) 0.0073(5) 0.0028(5) -0.0041(5) _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 1.3575(13) . . yes O1 C7 1.4353(14) . . yes O2 C3 1.3437(14) . . yes O3 C8 1.2487(15) . . yes O4 C13 1.3625(14) . . yes O4 C17 1.4291(15) . . yes O5 C14 1.3554(15) . . yes O5 C18 1.4327(15) . . yes O2 H2A 0.8400 . . no C1 C2 1.3851(15) . . no C1 C6 1.4049(15) . . no C2 C3 1.3966(15) . . no C3 C4 1.4142(15) . . no C4 C5 1.4072(15) . . no C4 C8 1.4680(17) . . no C5 C6 1.3710(15) . . no C8 C9 1.4700(16) . . no C9 C10 1.3374(18) . . no C10 C11 1.4569(16) . . no C11 C16 1.3919(16) . . no C11 C12 1.4073(18) . . no C12 C13 1.3818(17) . . no C13 C14 1.4102(16) . . no C14 C15 1.3886(18) . . no C15 C16 1.3909(17) . . no C2 H2 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7A 0.9800 . . no C7 H7B 0.9800 . . no C7 H7C 0.9800 . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C12 H12 0.9500 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17A 0.9800 . . no C17 H17B 0.9800 . . no C17 H17C 0.9800 . . no C18 H18A 0.9800 . . no C18 H18B 0.9800 . . no C18 H18C 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 C7 118.03(9) . . . yes C13 O4 C17 117.03(9) . . . yes C14 O5 C18 117.66(10) . . . yes C3 O2 H2A 109.00 . . . no O1 C1 C6 114.82(9) . . . yes C2 C1 C6 120.50(10) . . . no O1 C1 C2 124.69(10) . . . yes C1 C2 C3 119.63(10) . . . no O2 C3 C4 121.59(10) . . . yes C2 C3 C4 121.01(10) . . . no O2 C3 C2 117.40(10) . . . yes C3 C4 C8 119.80(10) . . . no C5 C4 C8 122.94(10) . . . no C3 C4 C5 117.26(10) . . . no C4 C5 C6 122.26(10) . . . no C1 C6 C5 119.31(10) . . . no O3 C8 C4 119.99(10) . . . yes O3 C8 C9 120.16(11) . . . yes C4 C8 C9 119.83(10) . . . no C8 C9 C10 120.74(11) . . . no C9 C10 C11 127.42(11) . . . no C10 C11 C12 118.18(10) . . . no C10 C11 C16 123.16(11) . . . no C12 C11 C16 118.66(11) . . . no C11 C12 C13 121.15(10) . . . no O4 C13 C12 125.03(10) . . . yes C12 C13 C14 119.54(11) . . . no O4 C13 C14 115.43(10) . . . yes O5 C14 C13 115.35(11) . . . yes O5 C14 C15 125.14(10) . . . yes C13 C14 C15 119.51(10) . . . no C14 C15 C16 120.52(11) . . . no C11 C16 C15 120.62(12) . . . no C1 C2 H2 120.00 . . . no C3 C2 H2 120.00 . . . no C4 C5 H5 119.00 . . . no C6 C5 H5 119.00 . . . no C1 C6 H6 120.00 . . . no C5 C6 H6 120.00 . . . no O1 C7 H7A 109.00 . . . no O1 C7 H7B 109.00 . . . no O1 C7 H7C 110.00 . . . no H7A C7 H7B 109.00 . . . no H7A C7 H7C 109.00 . . . no H7B C7 H7C 110.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C9 C10 H10 116.00 . . . no C11 C10 H10 116.00 . . . no C11 C12 H12 119.00 . . . no C13 C12 H12 119.00 . . . no C14 C15 H15 120.00 . . . no C16 C15 H15 120.00 . . . no C11 C16 H16 120.00 . . . no C15 C16 H16 120.00 . . . no O4 C17 H17A 109.00 . . . no O4 C17 H17B 109.00 . . . no O4 C17 H17C 109.00 . . . no H17A C17 H17B 109.00 . . . no H17A C17 H17C 109.00 . . . no H17B C17 H17C 110.00 . . . no O5 C18 H18A 110.00 . . . no O5 C18 H18B 109.00 . . . no O5 C18 H18C 109.00 . . . no H18A C18 H18B 110.00 . . . no H18A C18 H18C 109.00 . . . no H18B C18 H18C 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 C7 O1 C1 C2 -0.66(16) . . . . no C7 O1 C1 C6 178.67(9) . . . . no C17 O4 C13 C14 -169.55(10) . . . . no C17 O4 C13 C12 10.22(17) . . . . no C18 O5 C14 C15 -7.87(16) . . . . no C18 O5 C14 C13 172.20(10) . . . . no O1 C1 C6 C5 -178.33(10) . . . . no C6 C1 C2 C3 -0.47(16) . . . . no C2 C1 C6 C5 1.03(16) . . . . no O1 C1 C2 C3 178.82(10) . . . . no C1 C2 C3 C4 -0.94(16) . . . . no C1 C2 C3 O2 179.19(10) . . . . no C2 C3 C4 C5 1.74(16) . . . . no O2 C3 C4 C8 1.30(16) . . . . no C2 C3 C4 C8 -178.56(10) . . . . no O2 C3 C4 C5 -178.40(10) . . . . no C3 C4 C5 C6 -1.19(16) . . . . no C5 C4 C8 C9 -6.02(17) . . . . no C3 C4 C8 O3 -4.06(17) . . . . no C8 C4 C5 C6 179.12(11) . . . . no C3 C4 C8 C9 174.30(10) . . . . no C5 C4 C8 O3 175.63(11) . . . . no C4 C5 C6 C1 -0.17(17) . . . . no O3 C8 C9 C10 8.21(18) . . . . no C4 C8 C9 C10 -170.15(11) . . . . no C8 C9 C10 C11 177.23(11) . . . . no C9 C10 C11 C12 -178.28(12) . . . . no C9 C10 C11 C16 0.80(19) . . . . no C16 C11 C12 C13 0.06(17) . . . . no C10 C11 C16 C15 -179.05(11) . . . . no C12 C11 C16 C15 0.03(18) . . . . no C10 C11 C12 C13 179.17(11) . . . . no C11 C12 C13 C14 0.05(17) . . . . no C11 C12 C13 O4 -179.71(11) . . . . no O4 C13 C14 O5 -0.51(15) . . . . no C12 C13 C14 C15 -0.23(17) . . . . no O4 C13 C14 C15 179.56(10) . . . . no C12 C13 C14 O5 179.71(10) . . . . no O5 C14 C15 C16 -179.63(11) . . . . no C13 C14 C15 C16 0.31(17) . . . . no C14 C15 C16 C11 -0.21(18) . . . . 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 O3 2.5289(13) . . no O2 C5 3.4024(14) . 1_545 no O2 C7 3.1780(15) . 3_556 no O3 O2 2.5289(13) . . no O4 O5 2.5756(13) . . no O5 C17 3.3446(16) . 3_675 no O5 O4 2.5756(13) . . no O1 H16 2.7600 . 2_545 no O1 H9 2.7200 . 2_545 no O1 H5 2.7800 . 2_545 no O2 H15 2.8800 . 4_565 no O2 H7A 2.8400 . 3_556 no O3 H17C 2.6300 . 2_645 no O3 H2A 1.7800 . . no O3 H10 2.4300 . . no O3 H18B 2.8300 . 4_565 no O4 H18C 2.4500 . 3_685 no O5 H17A 2.5200 . 1_565 no O5 H17A 2.9100 . 3_675 no C1 C5 3.4272(15) . 2_545 no C1 C2 3.5381(15) . 3_566 no C2 C1 3.5381(15) . 3_566 no C3 C7 3.4589(16) . 3_566 no C5 O2 3.4024(14) . 1_565 no C5 C6 3.5612(15) . 2_555 no C5 C1 3.4272(15) . 2_555 no C6 C5 3.5612(15) . 2_545 no C7 O2 3.1780(15) . 3_556 no C7 C3 3.4589(16) . 3_566 no C10 C15 3.5881(17) . 1_545 no C12 C17 3.4989(17) . 2_655 no C13 C18 3.5317(16) . 1_545 no C15 C10 3.5881(17) . 1_565 no C17 C18 3.5652(17) . 3_675 no C17 C12 3.4989(17) . 2_645 no C17 O5 3.3446(16) . 3_675 no C18 C17 3.5652(17) . 3_675 no C18 C13 3.5317(16) . 1_565 no C1 H5 2.7800 . 2_545 no C2 H7A 2.9900 . 3_566 no C2 H7B 2.7700 . . no C2 H7A 2.7600 . . no C3 H7A 2.8500 . 3_566 no C4 H7A 2.8900 . 3_566 no C5 H6 3.0100 . 2_545 no C5 H7A 2.9900 . 3_566 no C5 H9 2.6500 . . no C6 H5 2.8400 . 2_545 no C7 H2 2.5300 . . no C8 H2A 2.3800 . . no C9 H5 2.6300 . . no C9 H16 2.7700 . . no C12 H17A 2.8100 . . no C12 H17B 2.6900 . . no C12 H18A 2.8700 . 1_545 no C12 H17B 2.8200 . 2_655 no C13 H18A 2.8700 . 1_545 no C13 H17B 2.8500 . 2_655 no C15 H18A 2.7200 . . no C15 H18B 2.8100 . . no C16 H7C 3.0900 . 2_555 no C16 H9 2.7700 . . no C17 H10 2.7700 . 2_655 no C17 H12 2.5200 . . no C18 H15 2.5300 . . no C18 H17C 3.1000 . 3_675 no H2 C7 2.5300 . . no H2 H7A 2.3000 . . no H2 H7B 2.3300 . . no H2A O3 1.7800 . . no H2A C8 2.3800 . . no H5 C9 2.6300 . . no H5 H9 2.0500 . . no H5 O1 2.7800 . 2_555 no H5 C1 2.7800 . 2_555 no H5 C6 2.8400 . 2_555 no H6 C5 3.0100 . 2_555 no H7A C2 2.7600 . . no H7A H2 2.3000 . . no H7A O2 2.8400 . 3_556 no H7A C2 2.9900 . 3_566 no H7A C3 2.8500 . 3_566 no H7A C4 2.8900 . 3_566 no H7A C5 2.9900 . 3_566 no H7B C2 2.7700 . . no H7B H2 2.3300 . . no H7C C16 3.0900 . 2_545 no H7C H15 2.5800 . 2_535 no H9 C5 2.6500 . . no H9 C16 2.7700 . . no H9 H5 2.0500 . . no H9 H16 2.2300 . . no H9 O1 2.7200 . 2_555 no H10 O3 2.4300 . . no H10 H12 2.3600 . . no H10 C17 2.7700 . 2_645 no H10 H17C 2.3100 . 2_645 no H12 C17 2.5200 . . no H12 H10 2.3600 . . no H12 H17A 2.4300 . . no H12 H17B 2.1900 . . no H15 C18 2.5300 . . no H15 H18A 2.2300 . . no H15 H18B 2.4200 . . no H15 H7C 2.5800 . 2_565 no H15 O2 2.8800 . 4_564 no H16 C9 2.7700 . . no H16 H9 2.2300 . . no H16 O1 2.7600 . 2_555 no H17A O5 2.5200 . 1_545 no H17A C12 2.8100 . . no H17A H12 2.4300 . . no H17A O5 2.9100 . 3_675 no H17B C12 2.6900 . . no H17B H12 2.1900 . . no H17B C12 2.8200 . 2_645 no H17B C13 2.8500 . 2_645 no H17C O3 2.6300 . 2_655 no H17C H10 2.3100 . 2_655 no H17C C18 3.1000 . 3_675 no H18A C12 2.8700 . 1_565 no H18A C13 2.8700 . 1_565 no H18A C15 2.7200 . . no H18A H15 2.2300 . . no H18B C15 2.8100 . . no H18B H15 2.4200 . . no H18B O3 2.8300 . 4_564 no H18C O4 2.4500 . 3_685 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 O2 H2A O3 0.8400 1.7800 2.5289(13) 147.00 . yes C10 H10 O3 0.9500 2.4300 2.7865(15) 102.00 . yes C17 H17A O5 0.9800 2.5200 3.4640(15) 162.00 1_545 yes C18 H18C O4 0.9800 2.4500 3.4255(16) 171.00 3_685 yes #===END