# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gabriel Lemcoff' _publ_contact_author_address ; Chemistry Ben-Gurion University of the Negev Beer-Sheva 84105 ISRAEL ; _publ_contact_author_email LEMCOFF@BGU.AC.IL _publ_section_title ; Facile Acetal Dynamic Combinatorial Library ; loop_ _publ_author_name 'Gabriel Lemcoff' 'Dvora Berkovich-Berger' #=============================================================================== data_e:\dv2\work\sol1\dvora22m _database_code_depnum_ccdc_archive 'CCDC 661726' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H34 N2 O12' # 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 'C26 H34 N2 O12' _chemical_formula_iupac ? _chemical_formula_weight 566.55 _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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.166(3) _cell_length_b 7.306(3) _cell_length_c 13.515(6) _cell_angle_alpha 90.475(7) _cell_angle_beta 103.007(7) _cell_angle_gamma 93.823(8) _cell_volume 687.7(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 4010 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 59.0 _cell_special_details ; ; _exptl_crystal_description 0.3 _exptl_crystal_colour yellow _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.35 _exptl_crystal_size_rad 0.35 _exptl_crystal_density_meas 1.37 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.109 _exptl_crystal_density_meas_temp 0 # Permitted for _exptl_absorpt_correction_type : # 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 integration # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.968 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device_type Smart1000 _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _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 4010 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.47 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measured_fraction_theta_full 0.960 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2721 # number of observed reflections (> n sig(I)) _reflns_number_gt 2047 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1176P)^2^+0.4168P] 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 mixed _refine_ls_extinction_method shelxl _refine_ls_extinction_coef 0 _refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2721 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2271 _refine_ls_wR_factor_gt 0.2074 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.099 _refine_ls_shift/su_mean 0.006 _refine_diff_density_max 0.468 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.059 #=============================================================================== # 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 0.6342(3) 1.1186(3) 0.26422(17) 1.000 0.0645(7) . . O2 O Uani 0.5685(3) 0.8801(3) 0.35807(16) 1.000 0.0674(7) . . O3 O Uani 0.6914(3) 0.6719(3) 0.54244(16) 1.000 0.0592(7) . . O4 O Uani 1.0666(2) 0.6010(3) 0.67325(14) 1.000 0.0552(6) . . O5 O Uani -0.1367(4) 0.6674(4) -0.0655(2) 1.000 0.0954(11) . . O6 O Uani -0.3198(4) 0.7548(6) 0.0258(2) 1.000 0.1250(16) . . N1 N Uani -0.1629(4) 0.7418(4) 0.0097(2) 1.000 0.0701(10) . . C1 C Uani 0.0047(4) 0.8196(4) 0.0857(2) 1.000 0.0547(8) . . C2 C Uani 0.7503(4) 0.4996(4) 0.5806(3) 1.000 0.0637(10) . . C3 C Uani 0.7320(5) 0.9249(5) 0.4390(3) 1.000 0.0715(11) . . C4 C Uani -0.0219(4) 0.9231(4) 0.1647(2) 1.000 0.0599(10) . . C5 C Uani 0.4907(4) 1.0305(4) 0.3081(2) 1.000 0.0588(9) . . C6 C Uani 0.1366(4) 0.9922(4) 0.2356(2) 1.000 0.0591(10) . . C7 C Uani 0.8889(4) 0.5139(4) 0.6825(3) 1.000 0.0632(10) . . C8 C Uani 1.2090(4) 0.6000(4) 0.7649(2) 1.000 0.0614(10) . . C9 C Uani 0.3168(4) 0.9565(4) 0.2277(2) 1.000 0.0561(9) . . C10 C Uani 0.8107(4) 0.7542(5) 0.4832(3) 1.000 0.0668(11) . . C11 C Uani 0.6085(4) 1.3081(5) 0.2511(3) 1.000 0.0659(10) . . C12 C Uani 0.1839(5) 0.7819(5) 0.0739(2) 1.000 0.0660(11) . . C13 C Uani 0.3406(5) 0.8512(5) 0.1469(3) 1.000 0.0696(11) . . H1 H Uiso 0.120(5) 1.060(5) 0.291(3) 1.000 0.076(10) . . H2 H Uiso -0.157(6) 0.942(5) 0.170(3) 1.000 0.074(10) . . H3 H Uiso 0.195(4) 0.712(4) 0.016(2) 1.000 0.057(8) . . H4 H Uiso 0.468(7) 0.844(6) 0.137(3) 1.000 0.101(13) . . H5 H Uiso 0.590(5) 1.359(5) 0.323(3) 1.000 0.075(10) . . H6 H Uiso 0.505(7) 1.326(7) 0.194(4) 1.000 0.125(17) . . H7 H Uiso 0.458(4) 1.122(4) 0.366(2) 1.000 0.057(8) . . H8 H Uiso 0.833(6) 0.998(5) 0.409(3) 1.000 0.081(10) . . H9 H Uiso 0.692(4) 0.998(4) 0.484(2) 1.000 0.046(8) . . H10 H Uiso 0.917(6) 0.777(5) 0.519(3) 1.000 0.075(10) . . H11 H Uiso 0.818(5) 0.676(5) 0.421(3) 1.000 0.082(11) . . H12 H Uiso 0.806(5) 0.438(4) 0.532(2) 1.000 0.058(8) . . H13 H Uiso 0.643(5) 0.421(4) 0.596(2) 1.000 0.054(7) . . H14 H Uiso 0.902(6) 0.392(6) 0.706(3) 1.000 0.093(12) . . H15 H Uiso 0.849(7) 0.578(6) 0.743(3) 1.000 0.111(15) . . H16 H Uiso 1.164(5) 0.659(5) 0.822(3) 1.000 0.070(9) . . H17 H Uiso 1.231(5) 0.478(6) 0.785(3) 1.000 0.083(11) . . 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 0.0556(12) 0.0579(12) 0.0781(14) 0.0082(10) 0.0160(10) -0.0134(9) O2 0.0527(11) 0.0642(12) 0.0709(13) 0.0191(10) -0.0111(10) -0.0163(9) O3 0.0435(10) 0.0544(11) 0.0774(13) 0.0106(9) 0.0086(9) 0.0031(8) O4 0.0405(10) 0.0565(11) 0.0616(11) 0.0098(8) -0.0012(8) -0.0051(8) O5 0.100(2) 0.096(2) 0.0739(17) -0.0081(14) -0.0095(14) -0.0095(16) O6 0.0566(16) 0.202(4) 0.104(2) -0.018(2) 0.0029(15) -0.0260(19) N1 0.0686(18) 0.0713(17) 0.0583(16) 0.0143(13) -0.0066(13) -0.0113(13) C1 0.0538(15) 0.0481(14) 0.0550(15) 0.0130(12) -0.0007(12) -0.0050(11) C2 0.0435(15) 0.0473(15) 0.090(2) 0.0044(15) -0.0047(15) -0.0039(12) C3 0.0616(19) 0.072(2) 0.0650(19) 0.0128(17) -0.0117(16) -0.0216(16) C4 0.0533(16) 0.0549(16) 0.0683(18) 0.0108(14) 0.0076(13) 0.0008(12) C5 0.0518(15) 0.0571(16) 0.0641(17) 0.0058(13) 0.0093(13) -0.0086(12) C6 0.0634(18) 0.0508(15) 0.0615(17) 0.0053(13) 0.0133(14) -0.0057(12) C7 0.0476(15) 0.0511(16) 0.084(2) 0.0201(15) 0.0027(14) -0.0075(12) C8 0.0531(16) 0.0576(17) 0.0641(18) 0.0197(14) -0.0052(14) -0.0036(13) C9 0.0578(16) 0.0525(15) 0.0523(15) 0.0096(12) 0.0041(12) -0.0102(12) C10 0.0390(15) 0.081(2) 0.073(2) 0.0112(17) -0.0004(14) -0.0046(14) C11 0.0453(15) 0.0658(18) 0.076(2) 0.0170(15) -0.0070(14) -0.0028(13) C12 0.0673(19) 0.0689(19) 0.0582(17) -0.0041(15) 0.0088(14) -0.0021(15) C13 0.0472(16) 0.082(2) 0.077(2) 0.0039(17) 0.0099(15) 0.0005(14) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C5 1.420(4) . . yes O1 C11 1.416(4) . . yes O2 C3 1.429(4) . . yes O2 C5 1.378(4) . . yes O3 C2 1.419(4) . . yes O3 C10 1.408(4) . . yes O4 C7 1.417(3) . . yes O4 C8 1.417(3) . . yes O5 N1 1.206(4) . . yes O6 N1 1.202(4) . . yes N1 C1 1.471(4) . . yes C1 C4 1.359(4) . . no C1 C12 1.374(5) . . no C2 C7 1.504(5) . . no C3 C10 1.478(5) . . no C4 C6 1.374(4) . . no C5 C9 1.522(4) . . no C6 C9 1.361(4) . . no C8 C11 1.490(4) . 2_776 no C9 C13 1.379(5) . . no C12 C13 1.381(5) . . no C2 H12 0.97(3) . . no C2 H13 0.99(3) . . no C3 H8 1.03(4) . . no C3 H9 0.91(3) . . no C4 H2 1.01(4) . . no C5 H7 1.10(3) . . no C6 H1 0.93(4) . . no C7 H14 0.95(4) . . no C7 H15 1.04(4) . . no C8 H16 1.01(4) . . no C8 H17 0.95(4) . . no C10 H10 0.81(4) . . no C10 H11 1.03(4) . . no C11 H5 1.08(4) . . no C11 H6 0.96(5) . . no C12 H3 0.95(3) . . no C13 H4 0.96(5) . . 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 C5 O1 C11 111.7(2) . . . yes C3 O2 C5 113.9(2) . . . yes C2 O3 C10 113.3(2) . . . yes C7 O4 C8 112.4(2) . . . yes O5 N1 O6 123.1(3) . . . yes O5 N1 C1 118.6(3) . . . yes O6 N1 C1 118.3(3) . . . yes N1 C1 C4 119.6(3) . . . yes N1 C1 C12 117.9(3) . . . yes C4 C1 C12 122.5(3) . . . no O3 C2 C7 113.4(3) . . . yes O2 C3 C10 109.5(3) . . . yes C1 C4 C6 118.7(3) . . . no O1 C5 O2 107.1(2) . . . yes O1 C5 C9 111.9(2) . . . yes O2 C5 C9 106.3(2) . . . yes C4 C6 C9 120.9(3) . . . no O4 C7 C2 110.2(3) . . . yes O4 C8 C11 109.2(2) . . 2_776 yes C5 C9 C6 120.3(2) . . . no C5 C9 C13 120.2(3) . . . no C6 C9 C13 119.5(3) . . . no O3 C10 C3 110.3(3) . . . yes O1 C11 C8 108.3(2) . . 2_776 yes C1 C12 C13 117.6(3) . . . no C9 C13 C12 120.8(3) . . . no O3 C2 H12 109.4(17) . . . no O3 C2 H13 112.2(19) . . . no C7 C2 H12 110.1(19) . . . no C7 C2 H13 101.5(16) . . . no H12 C2 H13 110(3) . . . no O2 C3 H8 108(2) . . . no O2 C3 H9 106.6(18) . . . no C10 C3 H8 110(2) . . . no C10 C3 H9 113.8(18) . . . no H8 C3 H9 109(3) . . . no C1 C4 H2 118(2) . . . no C6 C4 H2 123(2) . . . no O1 C5 H7 109.6(15) . . . no O2 C5 H7 106.8(14) . . . no C9 C5 H7 114.8(15) . . . no C4 C6 H1 119(2) . . . no C9 C6 H1 120(2) . . . no O4 C7 H14 112(3) . . . no O4 C7 H15 107(3) . . . no C2 C7 H14 107(2) . . . no C2 C7 H15 119(3) . . . no H14 C7 H15 101(3) . . . no O4 C8 H16 111(2) . . . no O4 C8 H17 110(2) . . . no H16 C8 H17 105(3) . . . no C11 C8 H16 112(2) 2_776 . . no C11 C8 H17 109(2) 2_776 . . no O3 C10 H10 109(3) . . . no O3 C10 H11 114(2) . . . no C3 C10 H10 110(3) . . . no C3 C10 H11 104(2) . . . no H10 C10 H11 111(3) . . . no O1 C11 H5 106(2) . . . no O1 C11 H6 110(3) . . . no H5 C11 H6 115(4) . . . no C8 C11 H5 107(2) 2_776 . . no C8 C11 H6 110(3) 2_776 . . no C1 C12 H3 119.3(18) . . . no C13 C12 H3 123.1(18) . . . no C9 C13 H4 118(3) . . . no C12 C13 H4 121(2) . . . 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 C11 O1 C5 O2 -153.9(2) . . . . no C11 O1 C5 C9 90.1(3) . . . . no C5 O1 C11 C8 163.2(2) . . . 2_776 no C5 O2 C3 C10 -176.7(3) . . . . no C3 O2 C5 O1 61.9(3) . . . . no C3 O2 C5 C9 -178.4(2) . . . . no C10 O3 C2 C7 89.9(3) . . . . no C2 O3 C10 C3 175.3(3) . . . . no C8 O4 C7 C2 -173.5(2) . . . . no C7 O4 C8 C11 179.4(2) . . . 2_776 no O5 N1 C1 C4 172.1(3) . . . . no O6 N1 C1 C4 -8.3(5) . . . . no O5 N1 C1 C12 -8.7(4) . . . . no O6 N1 C1 C12 171.0(3) . . . . no N1 C1 C4 C6 179.1(3) . . . . no C12 C1 C4 C6 -0.2(4) . . . . no N1 C1 C12 C13 -178.3(3) . . . . no C4 C1 C12 C13 0.9(5) . . . . no O3 C2 C7 O4 -67.8(3) . . . . no O2 C3 C10 O3 -74.1(4) . . . . no C1 C4 C6 C9 -0.7(4) . . . . no O1 C5 C9 C6 -131.1(3) . . . . no O1 C5 C9 C13 49.6(4) . . . . no O2 C5 C9 C6 112.4(3) . . . . no O2 C5 C9 C13 -67.0(3) . . . . no C4 C6 C9 C5 -178.6(3) . . . . no C4 C6 C9 C13 0.7(5) . . . . no O4 C8 C11 O1 69.1(3) . . 2_776 2_776 no C5 C9 C13 C12 179.4(3) . . . . no C6 C9 C13 C12 0.1(5) . . . . no C1 C12 C13 C9 -0.9(5) . . . . 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 O4 2.842(3) . 2_776 no O2 O3 2.924(3) . . no O3 C2 3.380(4) . 2_666 no O3 O2 2.924(3) . . no O3 O4 2.947(3) . . no O4 O3 2.947(3) . . no O4 C10 3.068(4) . . no O4 O1 2.842(3) . 2_776 no O5 C6 3.401(4) . 2_575 no O5 C12 3.276(5) . 2_565 no O6 C13 3.332(5) . 1_455 no O1 H4 2.67(4) . . no O1 H8 2.36(4) . . no O1 H2 2.57(4) . 1_655 no O2 H13 2.74(3) . 2_666 no O2 H4 2.92(4) . . no O3 H13 2.73(3) . 2_666 no O3 H7 2.39(3) . 2_676 no O4 H11 2.66(4) . 2_766 no O4 H10 2.52(4) . . no O5 H16 2.91(4) . 1_454 no O5 H15 2.64(4) . 1_454 no O5 H3 2.88(3) . 2_565 no O5 H6 2.82(5) . 2_575 no O5 H3 2.38(3) . . no O6 H2 2.40(4) . . no O6 H4 2.48(5) . 1_455 no C1 C1 3.518(4) . 2_575 no C2 O3 3.380(4) . 2_666 no C6 O5 3.401(4) . 2_575 no C10 O4 3.068(4) . . no C12 O5 3.276(5) . 2_565 no C13 O6 3.332(5) . 1_655 no C4 H14 2.96(4) . 2_666 no C6 H14 2.93(4) . 2_666 no C7 H10 2.97(4) . . no C9 H6 3.02(5) . . no C10 H8 3.10(4) . 2_776 no H1 H7 2.42(5) . . no H2 O1 2.57(4) . 1_455 no H2 O6 2.40(4) . . no H3 O5 2.38(3) . . no H3 O5 2.88(3) . 2_565 no H4 O1 2.67(4) . . no H4 O2 2.92(4) . . no H4 O6 2.48(5) . 1_655 no H5 H7 2.07(5) . . no H6 C9 3.02(5) . . no H6 O5 2.82(5) . 2_575 no H7 H1 2.42(5) . . no H7 H5 2.07(5) . . no H7 H9 2.28(4) . . no H7 O3 2.39(3) . 2_676 no H8 O1 2.36(4) . . no H8 C10 3.10(4) . 2_776 no H8 H10 2.38(6) . 2_776 no H9 H7 2.28(4) . . no H10 O4 2.52(4) . . no H10 C7 2.97(4) . . no H10 H12 2.57(5) . . no H10 H8 2.38(6) . 2_776 no H11 H12 2.32(5) . . no H11 O4 2.66(4) . 2_766 no H12 H10 2.57(5) . . no H12 H11 2.32(5) . . no H13 O2 2.74(3) . 2_666 no H13 O3 2.73(3) . 2_666 no H14 H17 2.40(6) . . no H14 C4 2.96(4) . 2_666 no H14 C6 2.93(4) . 2_666 no H15 O5 2.64(4) . 1_656 no H15 H16 2.31(6) . . no H16 O5 2.91(4) . 1_656 no H16 H15 2.31(6) . . no H17 H14 2.40(6) . . 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 # #D H A D - H H...A D...A D - H...A symm(A) # C4 H2 O1 1.01(4) 2.57(4) 3.443(4) 145(3) 1_455 yes C13 H4 O6 0.96(5) 2.48(5) 3.332(5) 149(3) 1_655 yes C5 H7 O3 1.10(3) 2.39(3) 3.465(4) 164(2) 2_676 yes C3 H8 O1 1.03(4) 2.36(4) 2.742(5) 101(3) . yes C10 H10 O4 0.81(4) 2.52(4) 3.068(4) 126(3) . yes # Attachment 'M1lem.cif' # CIF-file generated for 666 Pbca R = 0.05 #=============================================================================== data_666 _database_code_depnum_ccdc_archive 'CCDC 674793' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N O6' # 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 H17 N O6' _chemical_formula_iupac ? _chemical_formula_weight 283.28 _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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 0.0033 0.0016 '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 b c a' _symmetry_Int_Tables_number 61 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 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z _cell_length_a 15.714(3) _cell_length_b 8.2622(15) _cell_length_c 20.989(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2725.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2013 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25.06 _cell_special_details ; Least Squares Treatment of 25 SET4 setting angles. ; _exptl_crystal_description cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.19 _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9891 _exptl_crystal_density_meas_temp ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _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 14250 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.16 _diffrn_reflns_theta_full 26.16 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2704 # number of observed reflections (> n sig(I)) _reflns_number_gt 1288 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0913P)^2^] 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 mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2704 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1218 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.007 _refine_diff_density_max 0.138 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.039 #=============================================================================== # 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 0.33482(15) -0.3630(3) 0.60541(13) 1.000 0.0930(10) . . O2 O Uani 0.41127(17) -0.4811(3) 0.53581(12) 1.000 0.0981(10) . . O3 O Uani 0.45084(12) 0.2145(2) 0.36466(10) 1.000 0.0649(7) . . O4 O Uani 0.30809(12) 0.2598(2) 0.38921(9) 1.000 0.0611(7) . . O5 O Uani 0.27652(14) 0.3010(2) 0.25522(11) 1.000 0.0758(9) . . O6 O Uani 0.46434(15) 0.2118(2) 0.22728(11) 1.000 0.0801(9) . . N1 N Uani 0.37484(17) -0.3624(3) 0.55607(14) 1.000 0.0674(10) . . C1 C Uani 0.38094(16) -0.2109(3) 0.51987(14) 1.000 0.0539(10) . . C2 C Uani 0.39083(16) 0.0710(3) 0.45070(14) 1.000 0.0528(10) . . C3 C Uani 0.38992(18) 0.2255(4) 0.41279(15) 1.000 0.0555(10) . . C4 C Uani 0.4593(2) 0.3609(4) 0.32761(16) 1.000 0.0647(11) . . C5 C Uani 0.4313(2) -0.0674(4) 0.42979(16) 1.000 0.0596(11) . . C6 C Uani 0.34630(19) 0.0656(4) 0.50753(15) 1.000 0.0617(11) . . C7 C Uani 0.4264(2) -0.2096(4) 0.46404(15) 1.000 0.0618(11) . . C8 C Uani 0.3407(2) -0.0750(4) 0.54210(17) 1.000 0.0633(11) . . C9 C Uani 0.2244(2) 0.2098(4) 0.2962(2) 1.000 0.0763(14) . . C10 C Uani 0.2742(3) 0.1341(4) 0.3482(2) 1.000 0.0755(13) . . C11 C Uani 0.3142(3) 0.2096(6) 0.2042(2) 1.000 0.0920(17) . . C12 C Uani 0.5084(2) 0.3198(4) 0.26914(18) 1.000 0.0737(14) . . C13 C Uani 0.3997(3) 0.2753(5) 0.1881(2) 1.000 0.0907(19) . . H1 H Uiso 0.1849(19) 0.291(4) 0.3172(14) 1.000 0.072(9) . . H2 H Uiso 0.1921(18) 0.121(4) 0.2718(14) 1.000 0.074(9) . . H3 H Uiso 0.241(2) 0.067(4) 0.3736(16) 1.000 0.093(12) . . H4 H Uiso 0.396(2) 0.409(4) 0.3100(15) 1.000 0.088(9) . . H5 H Uiso 0.4880(17) 0.439(3) 0.3527(12) 1.000 0.060(8) . . H6 H Uiso 0.3120(18) -0.076(4) 0.5795(15) 1.000 0.065(9) . . H7 H Uiso 0.4013(16) 0.316(4) 0.4397(13) 1.000 0.062(8) . . H8 H Uiso 0.4603(18) -0.066(3) 0.3919(15) 1.000 0.074(10) . . H9 H Uiso 0.455(2) -0.297(5) 0.4521(17) 1.000 0.106(13) . . H10 H Uiso 0.322(2) 0.063(4) 0.3328(15) 1.000 0.079(10) . . H11 H Uiso 0.5231(18) 0.419(4) 0.2445(15) 1.000 0.084(10) . . H12 H Uiso 0.314(2) 0.160(4) 0.5232(15) 1.000 0.084(10) . . H13 H Uiso 0.400(2) 0.394(5) 0.1915(16) 1.000 0.095(11) . . H14 H Uiso 0.566(3) 0.256(5) 0.2768(18) 1.000 0.113(12) . . H15 H Uiso 0.273(2) 0.217(5) 0.166(2) 1.000 0.119(13) . . H16 H Uiso 0.310(3) 0.092(6) 0.216(2) 1.000 0.138(16) . . H17 H Uiso 0.410(2) 0.230(5) 0.143(2) 1.000 0.110(13) . . 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 0.1002(18) 0.0919(18) 0.0870(18) 0.0340(14) 0.0284(15) 0.0092(13) O2 0.140(2) 0.0617(15) 0.0925(18) 0.0121(13) 0.0128(16) 0.0202(14) O3 0.0638(12) 0.0564(12) 0.0744(14) 0.0138(10) 0.0121(11) 0.0032(9) O4 0.0616(11) 0.0475(11) 0.0742(14) -0.0001(10) -0.0095(11) 0.0058(9) O5 0.0951(16) 0.0473(11) 0.0851(17) -0.0018(12) -0.0193(13) 0.0037(11) O6 0.1062(17) 0.0521(12) 0.0819(15) -0.0077(11) -0.0034(14) 0.0049(11) N1 0.0650(16) 0.0697(19) 0.0674(19) 0.0124(15) -0.0024(14) 0.0001(14) C1 0.0521(15) 0.0561(17) 0.0534(18) 0.0095(14) -0.0039(14) 0.0018(13) C2 0.0465(14) 0.0535(17) 0.0583(19) -0.0001(14) -0.0043(14) 0.0025(12) C3 0.0569(17) 0.0500(17) 0.0595(19) -0.0005(15) -0.0018(15) -0.0022(13) C4 0.078(2) 0.0461(17) 0.070(2) 0.0030(16) 0.0043(18) -0.0078(16) C5 0.0661(18) 0.0603(19) 0.0525(19) 0.0069(15) 0.0089(16) 0.0078(15) C6 0.0641(18) 0.0600(19) 0.061(2) 0.0013(16) 0.0105(16) 0.0084(15) C7 0.0694(19) 0.0561(19) 0.060(2) 0.0029(16) 0.0027(16) 0.0142(15) C8 0.0658(19) 0.068(2) 0.056(2) 0.0055(16) 0.0144(17) 0.0041(16) C9 0.069(2) 0.056(2) 0.104(3) 0.000(2) -0.026(2) -0.0029(17) C10 0.075(2) 0.0484(18) 0.103(3) 0.008(2) -0.027(2) -0.0129(18) C11 0.115(3) 0.084(3) 0.077(3) -0.020(2) -0.030(3) 0.002(2) C12 0.089(2) 0.0551(19) 0.077(3) -0.0013(18) 0.014(2) -0.0105(18) C13 0.135(4) 0.072(3) 0.065(3) 0.003(2) -0.009(2) 0.008(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 N1 1.212(4) . . yes O2 N1 1.213(4) . . yes O3 C3 1.395(4) . . yes O3 C4 1.444(4) . . yes O4 C3 1.407(3) . . yes O4 C10 1.450(4) . . yes O5 C9 1.407(4) . . yes O5 C11 1.438(5) . . yes O6 C12 1.431(4) . . yes O6 C13 1.408(5) . . yes N1 C1 1.467(4) . . yes C1 C7 1.372(4) . . no C1 C8 1.371(4) . . no C2 C3 1.504(4) . . no C2 C5 1.380(4) . . no C2 C6 1.384(4) . . no C4 C12 1.489(5) . . no C5 C7 1.380(5) . . no C6 C8 1.373(5) . . no C9 C10 1.482(6) . . no C11 C13 1.488(7) . . no C3 H7 0.95(3) . . no C4 H4 1.13(3) . . no C4 H5 0.95(3) . . no C5 H8 0.92(3) . . no C6 H12 0.99(3) . . no C7 H9 0.89(4) . . no C8 H6 0.91(3) . . no C9 H1 1.02(3) . . no C9 H2 1.03(3) . . no C10 H3 0.93(3) . . no C10 H10 1.01(3) . . no C11 H15 1.03(4) . . no C11 H16 1.01(5) . . no C12 H11 1.00(3) . . no C12 H14 1.06(5) . . no C13 H13 0.98(4) . . no C13 H17 1.03(4) . . 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 C3 O3 C4 113.5(2) . . . yes C3 O4 C10 113.6(2) . . . yes C9 O5 C11 114.5(3) . . . yes C12 O6 C13 118.4(2) . . . yes O1 N1 O2 122.8(3) . . . yes O1 N1 C1 118.7(2) . . . yes O2 N1 C1 118.5(3) . . . yes N1 C1 C7 118.9(2) . . . yes N1 C1 C8 119.5(3) . . . yes C7 C1 C8 121.6(3) . . . no C3 C2 C5 122.6(3) . . . no C3 C2 C6 118.6(2) . . . no C5 C2 C6 118.7(3) . . . no O3 C3 O4 112.7(2) . . . yes O3 C3 C2 108.7(2) . . . yes O4 C3 C2 111.5(2) . . . yes O3 C4 C12 107.5(3) . . . yes C2 C5 C7 121.0(3) . . . no C2 C6 C8 121.0(3) . . . no C1 C7 C5 118.7(3) . . . no C1 C8 C6 118.9(3) . . . no O5 C9 C10 111.7(3) . . . yes O4 C10 C9 109.2(3) . . . yes O5 C11 C13 110.5(4) . . . yes O6 C12 C4 113.4(3) . . . yes O6 C13 C11 112.5(3) . . . yes O3 C3 H7 110.6(16) . . . no O4 C3 H7 102.8(16) . . . no C2 C3 H7 110.5(18) . . . no O3 C4 H4 112.9(17) . . . no O3 C4 H5 108.4(15) . . . no C12 C4 H4 105.4(16) . . . no C12 C4 H5 111.5(16) . . . no H4 C4 H5 111(2) . . . no C2 C5 H8 119.6(16) . . . no C7 C5 H8 119.4(16) . . . no C2 C6 H12 121.5(19) . . . no C8 C6 H12 117.4(19) . . . no C1 C7 H9 120(2) . . . no C5 C7 H9 121(2) . . . no C1 C8 H6 121(2) . . . no C6 C8 H6 120(2) . . . no O5 C9 H1 105.5(18) . . . no O5 C9 H2 111.4(17) . . . no C10 C9 H1 106.4(17) . . . no C10 C9 H2 109.0(18) . . . no H1 C9 H2 113(2) . . . no O4 C10 H3 107(2) . . . no O4 C10 H10 109.5(19) . . . no C9 C10 H3 112(2) . . . no C9 C10 H10 113.8(18) . . . no H3 C10 H10 105(3) . . . no O5 C11 H15 107(2) . . . no O5 C11 H16 107(2) . . . no C13 C11 H15 112(2) . . . no C13 C11 H16 118(3) . . . no H15 C11 H16 102(3) . . . no O6 C12 H11 107.9(18) . . . no O6 C12 H14 101(2) . . . no C4 C12 H11 111.1(18) . . . no C4 C12 H14 116(2) . . . no H11 C12 H14 107(3) . . . no O6 C13 H13 109.0(19) . . . no O6 C13 H17 107(2) . . . no C11 C13 H13 110.6(19) . . . no C11 C13 H17 102.6(19) . . . no H13 C13 H17 115(3) . . . 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 O3 C3 O4 59.6(3) . . . . no C4 O3 C3 C2 -176.3(2) . . . . no C3 O3 C4 C12 -165.8(2) . . . . no C10 O4 C3 O3 63.4(3) . . . . no C10 O4 C3 C2 -59.2(3) . . . . no C3 O4 C10 C9 -143.5(3) . . . . no C11 O5 C9 C10 87.1(4) . . . . no C9 O5 C11 C13 -147.0(3) . . . . no C13 O6 C12 C4 78.1(4) . . . . no C12 O6 C13 C11 -115.0(4) . . . . no O1 N1 C1 C7 179.8(3) . . . . no O2 N1 C1 C7 1.0(4) . . . . no O1 N1 C1 C8 -0.8(4) . . . . no O2 N1 C1 C8 -179.6(3) . . . . no N1 C1 C7 C5 179.4(3) . . . . no C8 C1 C7 C5 0.0(5) . . . . no N1 C1 C8 C6 -179.5(3) . . . . no C7 C1 C8 C6 -0.1(5) . . . . no C5 C2 C3 O3 -14.0(4) . . . . no C5 C2 C3 O4 110.9(3) . . . . no C6 C2 C3 O3 168.8(2) . . . . no C6 C2 C3 O4 -66.4(3) . . . . no C3 C2 C5 C7 -176.0(3) . . . . no C6 C2 C5 C7 1.2(4) . . . . no C3 C2 C6 C8 176.0(3) . . . . no C5 C2 C6 C8 -1.3(4) . . . . no O3 C4 C12 O6 66.0(3) . . . . no C2 C5 C7 C1 -0.5(5) . . . . no C2 C6 C8 C1 0.8(5) . . . . no O5 C9 C10 O4 66.1(4) . . . . no O5 C11 C13 O6 85.0(4) . . . . 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 C11 3.375(5) . 2_555 no O2 O2 3.183(4) . 5_646 no O3 O6 2.891(3) . . no O4 O5 2.876(3) . . no O5 O4 2.876(3) . . no O5 O6 3.098(3) . . no O5 C4 3.287(4) . . no O6 O5 3.098(3) . . no O6 C4 3.343(4) . 4_645 no O6 C12 3.268(4) . 4_645 no O6 O3 2.891(3) . . no O1 H12 2.91(3) . 7_545 no O1 H6 2.46(3) . . no O1 H15 2.44(4) . 2_555 no O2 H7 2.63(3) . 1_545 no O2 H9 2.42(4) . . no O2 H5 2.85(3) . 5_656 no O2 H9 2.80(4) . 5_646 no O3 H8 2.39(3) . . no O3 H10 2.47(3) . . no O4 H4 2.49(3) . . no O4 H3 2.67(3) . 7_555 no O5 H2 2.71(3) . 7_555 no O5 H16 2.88(5) . 7_555 no O5 H4 2.38(3) . . no O6 H5 2.91(3) . 4_645 no O6 H11 2.50(3) . 4_645 no C2 C7 3.572(4) . 5_656 no C4 O5 3.287(4) . . no C4 C10 3.487(5) . . no C4 O6 3.343(4) . 4_655 no C5 C10 3.435(5) . . no C6 C10 3.576(5) . . no C7 C2 3.572(4) . 5_656 no C10 C4 3.487(5) . . no C10 C6 3.576(5) . . no C10 C5 3.435(5) . . no C11 O1 3.375(5) . 2_554 no C12 O6 3.268(4) . 4_655 no C2 H10 2.70(3) . . no C2 H3 2.86(3) . . no C4 H13 3.02(3) . . no C5 H10 2.87(3) . . no C9 H14 2.95(4) . 6_455 no C10 H16 2.85(4) . . no C10 H4 3.08(3) . . no C10 H1 2.98(3) . 7_545 no C11 H10 2.96(3) . . no C11 H4 3.05(3) . . no C13 H4 2.79(3) . . no C13 H8 3.06(3) . 4_655 no H1 C10 2.98(3) . 7_555 no H1 H10 2.27(5) . 7_555 no H2 H16 2.21(5) . . no H2 H14 2.49(5) . 6_455 no H2 O5 2.71(3) . 7_545 no H2 H4 2.37(4) . 7_545 no H3 C2 2.86(3) . . no H3 O4 2.67(3) . 7_545 no H4 O4 2.49(3) . . no H4 O5 2.38(3) . . no H4 C10 3.08(3) . . no H4 C11 3.05(3) . . no H4 C13 2.79(3) . . no H4 H13 2.49(5) . . no H4 H2 2.37(4) . 7_555 no H5 H7 2.50(4) . . no H5 O6 2.91(3) . 4_655 no H5 O2 2.85(3) . 5_656 no H6 O1 2.46(3) . . no H6 H15 2.54(5) . 2_555 no H7 O2 2.63(3) . 1_565 no H7 H5 2.50(4) . . no H7 H12 2.57(4) . . no H8 O3 2.39(3) . . no H8 C13 3.06(3) . 4_645 no H9 O2 2.42(4) . . no H9 O2 2.80(4) . 5_646 no H10 O3 2.47(3) . . no H10 C2 2.70(3) . . no H10 C5 2.87(3) . . no H10 C11 2.96(3) . . no H10 H16 2.47(5) . . no H10 H1 2.27(5) . 7_545 no H11 H13 2.24(4) . . no H11 O6 2.50(3) . 4_655 no H12 H7 2.57(4) . . no H12 O1 2.91(3) . 7_555 no H13 C4 3.02(3) . . no H13 H4 2.49(5) . . no H13 H11 2.24(4) . . no H14 C9 2.95(4) . 6_555 no H14 H2 2.49(5) . 6_555 no H15 O1 2.44(4) . 2_554 no H15 H6 2.54(5) . 2_554 no H16 C10 2.85(4) . . no H16 H2 2.21(5) . . no H16 H10 2.47(5) . . no H16 O5 2.88(5) . 7_545 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 # #D H A D - H H...A D...A D - H...A symm(A) # C4 H4 O5 1.13(3) 2.38(3) 3.287(4) 136(2) . yes C5 H8 O3 0.92(3) 2.39(3) 2.718(4) 100.9(18) . yes C10 H10 O3 1.01(3) 2.47(3) 2.875(5) 103(2) . yes C12 H11 O6 1.00(3) 2.50(3) 3.268(4) 134(2) 4_655 yes C11 H15 O1 1.03(4) 2.44(4) 3.375(5) 151(3) 2_554 yes