# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Reiser, Oliver' _publ_contact_author_name 'Reiser, Oliver' _publ_contact_author_email Oliver.Reiser@chemie.uni-regensburg.de _publ_section_title ; Enantioselective Synthesis of (-)-Paeonilide ; # Attachment '- compound_1.cif' # CIF-file generated for l:\axray\k191\k191 R = 0.04 #============================================================================== data_k191 _database_code_depnum_ccdc_archive 'CCDC 861132' #TrackingRef '- compound_1.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 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 'C17 H18 O6' _chemical_formula_iupac ? _chemical_formula_weight 318.31 _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 9.9890(2) _cell_length_b 6.47394(13) _cell_length_c 12.1110(3) _cell_angle_alpha 90 _cell_angle_beta 99.014(2) _cell_angle_gamma 90 _cell_volume 773.52(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123 _cell_measurement_reflns_used 3120 _cell_measurement_theta_min 3.6922 _cell_measurement_theta_max 72.7346 _cell_special_details ; ; _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2041 _exptl_crystal_size_mid 0.0467 _exptl_crystal_size_min 0.0293 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.870 _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 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 0.884 _exptl_absorpt_correction_T_max 0.975 #=============================================================================== # 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 '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 5084 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 72.89 _diffrn_reflns_theta_full 72.89 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2940 # number of observed reflections (> n sig(I)) _reflns_number_gt 2830 _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^)+(0.0826P)^2^+0.0733P] 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 0.13(18) # 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 2940 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.297 _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 0.38839(17) 0.4619(2) 0.46724(13) 1.000 0.0354(4) . . O2 O Uani 0.29113(14) 0.1556(2) 0.41906(12) 1.000 0.0311(4) . . O3 O Uani 0.03571(13) -0.1675(2) 0.56187(12) 1.000 0.0309(4) . . O4 O Uani 0.08549(14) -0.4031(2) 0.70682(12) 1.000 0.0309(4) . . O5 O Uani 0.21655(17) -0.6608(2) 0.78287(13) 1.000 0.0391(5) . . O6 O Uani 0.17794(15) -0.1494(2) 0.90610(12) 1.000 0.0346(4) . . C1 C Uani 0.34791(18) 0.3351(3) 0.39725(17) 1.000 0.0275(5) . . C2 C Uani 0.35621(19) 0.3603(3) 0.27575(17) 1.000 0.0294(5) . . C3 C Uani 0.3242(2) 0.2012(4) 0.19904(18) 1.000 0.0345(6) . . C4 C Uani 0.3362(2) 0.2339(5) 0.0872(2) 1.000 0.0420(7) . . C5 C Uani 0.3779(2) 0.4236(5) 0.0533(2) 1.000 0.0465(8) . . C6 C Uani 0.4082(3) 0.5826(5) 0.1287(2) 1.000 0.0471(8) . . C7 C Uani 0.3980(2) 0.5518(4) 0.24094(19) 1.000 0.0370(6) . . C8 C Uani 0.2750(2) 0.1233(3) 0.53450(15) 1.000 0.0281(5) . . C9 C Uani 0.26568(19) -0.1073(3) 0.55328(16) 1.000 0.0261(5) . . C10 C Uani 0.1368(2) -0.2015(3) 0.49019(16) 1.000 0.0298(5) . . C11 C Uani 0.09805(19) -0.1885(3) 0.67199(16) 1.000 0.0278(5) . . C12 C Uani 0.2067(2) -0.4895(3) 0.74338(16) 1.000 0.0290(5) . . C13 C Uani 0.32003(19) -0.3483(3) 0.72482(16) 1.000 0.0277(5) . . C14 C Uani 0.25245(18) -0.1498(3) 0.67637(15) 1.000 0.0245(5) . . C15 C Uani 0.02211(19) -0.0563(3) 0.74407(19) 1.000 0.0316(6) . . C16 C Uani 0.0793(2) -0.0503(3) 0.86634(18) 1.000 0.0317(6) . . C17 C Uani 0.0058(3) 0.0891(4) 0.9352(2) 1.000 0.0425(7) . . H3 H Uiso 0.29440 0.07140 0.22260 1.000 0.0410 calc R H4 H Uiso 0.31560 0.12560 0.03440 1.000 0.0500 calc R H5 H Uiso 0.38590 0.44480 -0.02300 1.000 0.0560 calc R H6 H Uiso 0.43590 0.71290 0.10420 1.000 0.0560 calc R H7 H Uiso 0.41950 0.66050 0.29340 1.000 0.0440 calc R H8A H Uiso 0.19160 0.19250 0.55020 1.000 0.0340 calc R H8B H Uiso 0.35340 0.18160 0.58500 1.000 0.0340 calc R H9 H Uiso 0.34720 -0.17900 0.53310 1.000 0.0310 calc R H10A H Uiso 0.11040 -0.13260 0.41700 1.000 0.0360 calc R H10B H Uiso 0.14900 -0.35090 0.47750 1.000 0.0360 calc R H13A H Uiso 0.37450 -0.41090 0.67190 1.000 0.0330 calc R H13B H Uiso 0.38020 -0.31990 0.79620 1.000 0.0330 calc R H14 H Uiso 0.28330 -0.02830 0.72470 1.000 0.0290 calc R H15A H Uiso 0.01900 0.08680 0.71490 1.000 0.0380 calc R H15B H Uiso -0.07240 -0.10690 0.73610 1.000 0.0380 calc R H17A H Uiso 0.06800 0.19580 0.97020 1.000 0.0640 calc R H17B H Uiso -0.02820 0.00810 0.99330 1.000 0.0640 calc R H17C H Uiso -0.07050 0.15450 0.88710 1.000 0.0640 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 0.0439(8) 0.0285(7) 0.0359(8) -0.0039(6) 0.0128(6) -0.0039(6) O2 0.0349(7) 0.0304(7) 0.0279(7) 0.0018(5) 0.0051(5) -0.0057(6) O3 0.0223(6) 0.0370(7) 0.0321(7) -0.0004(6) 0.0002(5) -0.0017(6) O4 0.0277(7) 0.0270(7) 0.0380(7) 0.0008(6) 0.0050(5) -0.0059(5) O5 0.0506(9) 0.0249(7) 0.0427(8) 0.0053(6) 0.0100(7) -0.0015(6) O6 0.0355(7) 0.0380(8) 0.0312(7) 0.0010(6) 0.0083(6) 0.0016(7) C1 0.0226(8) 0.0275(9) 0.0335(9) 0.0019(8) 0.0078(7) 0.0030(7) C2 0.0214(8) 0.0370(10) 0.0305(10) 0.0043(8) 0.0063(7) 0.0040(8) C3 0.0271(9) 0.0440(12) 0.0327(10) -0.0005(9) 0.0058(8) 0.0038(8) C4 0.0301(11) 0.0639(15) 0.0316(11) -0.0025(10) 0.0037(8) 0.0054(10) C5 0.0361(11) 0.0729(18) 0.0318(11) 0.0135(11) 0.0096(9) 0.0076(11) C6 0.0407(12) 0.0603(16) 0.0428(12) 0.0181(12) 0.0148(10) -0.0003(11) C7 0.0332(10) 0.0392(11) 0.0395(11) 0.0093(10) 0.0084(9) -0.0002(9) C8 0.0322(9) 0.0263(9) 0.0255(9) 0.0014(7) 0.0035(7) -0.0025(7) C9 0.0238(8) 0.0259(9) 0.0284(9) 0.0015(7) 0.0036(7) -0.0014(7) C10 0.0289(9) 0.0324(10) 0.0275(9) -0.0010(7) 0.0024(7) -0.0040(8) C11 0.0243(9) 0.0269(9) 0.0314(9) 0.0019(8) 0.0022(7) -0.0038(7) C12 0.0341(10) 0.0252(9) 0.0283(9) -0.0013(7) 0.0067(7) -0.0005(7) C13 0.0255(8) 0.0274(9) 0.0303(9) 0.0036(7) 0.0047(7) 0.0024(7) C14 0.0217(8) 0.0244(8) 0.0271(8) 0.0003(7) 0.0034(6) -0.0015(7) C15 0.0209(8) 0.0327(10) 0.0422(11) 0.0018(8) 0.0080(8) 0.0001(7) C16 0.0303(9) 0.0275(9) 0.0397(11) 0.0002(8) 0.0129(8) -0.0052(8) C17 0.0425(12) 0.0413(12) 0.0473(13) -0.0046(10) 0.0187(10) 0.0023(10) _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 1.338(2) . . yes O2 C8 1.447(2) . . yes O3 C10 1.448(2) . . yes O3 C11 1.387(2) . . yes O4 C11 1.463(2) . . yes O4 C12 1.344(2) . . yes O5 C12 1.206(2) . . yes O6 C16 1.211(2) . . yes C1 C2 1.496(3) . . no C2 C3 1.390(3) . . no C2 C7 1.394(3) . . no C3 C4 1.395(3) . . no C4 C5 1.380(4) . . no C5 C6 1.378(4) . . no C6 C7 1.393(3) . . no C8 C9 1.515(3) . . no C9 C10 1.518(3) . . no C9 C14 1.542(3) . . no C11 C14 1.555(3) . . no C11 C15 1.509(3) . . no C12 C13 1.499(3) . . no C13 C14 1.526(3) . . no C15 C16 1.502(3) . . no C16 C17 1.497(3) . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8A 0.9900 . . no C8 H8B 0.9900 . . no C9 H9 1.0000 . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C13 H13A 0.9900 . . no C13 H13B 0.9900 . . no C14 H14 1.0000 . . no C15 H15A 0.9900 . . no C15 H15B 0.9900 . . no C17 H17A 0.9800 . . no C17 H17B 0.9800 . . no C17 H17C 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 C8 115.54(15) . . . yes C10 O3 C11 108.14(14) . . . yes C11 O4 C12 112.12(15) . . . yes O1 C1 O2 124.03(19) . . . yes O1 C1 C2 123.66(18) . . . yes O2 C1 C2 112.31(17) . . . yes C1 C2 C3 122.29(18) . . . no C1 C2 C7 117.38(18) . . . no C3 C2 C7 120.3(2) . . . no C2 C3 C4 119.4(2) . . . no C3 C4 C5 120.0(3) . . . no C4 C5 C6 120.9(2) . . . no C5 C6 C7 119.8(3) . . . no C2 C7 C6 119.6(2) . . . no O2 C8 C9 107.83(15) . . . yes C8 C9 C10 112.80(16) . . . no C8 C9 C14 109.73(15) . . . no C10 C9 C14 102.74(15) . . . no O3 C10 C9 104.67(15) . . . yes O3 C11 O4 108.93(15) . . . yes O3 C11 C14 108.08(15) . . . yes O3 C11 C15 108.05(16) . . . yes O4 C11 C14 105.82(15) . . . yes O4 C11 C15 107.35(15) . . . yes C14 C11 C15 118.33(16) . . . no O4 C12 O5 121.79(19) . . . yes O4 C12 C13 111.05(16) . . . yes O5 C12 C13 127.14(19) . . . yes C12 C13 C14 105.80(15) . . . no C9 C14 C11 103.33(15) . . . no C9 C14 C13 114.99(16) . . . no C11 C14 C13 104.72(15) . . . no C11 C15 C16 115.91(17) . . . no O6 C16 C15 122.59(18) . . . yes O6 C16 C17 122.5(2) . . . yes C15 C16 C17 114.89(18) . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C2 C7 H7 120.00 . . . no C6 C7 H7 120.00 . . . no O2 C8 H8A 110.00 . . . no O2 C8 H8B 110.00 . . . no C9 C8 H8A 110.00 . . . no C9 C8 H8B 110.00 . . . no H8A C8 H8B 108.00 . . . no C8 C9 H9 110.00 . . . no C10 C9 H9 110.00 . . . no C14 C9 H9 110.00 . . . no O3 C10 H10A 111.00 . . . no O3 C10 H10B 111.00 . . . no C9 C10 H10A 111.00 . . . no C9 C10 H10B 111.00 . . . no H10A C10 H10B 109.00 . . . no C12 C13 H13A 111.00 . . . no C12 C13 H13B 111.00 . . . no C14 C13 H13A 111.00 . . . no C14 C13 H13B 111.00 . . . no H13A C13 H13B 109.00 . . . no C9 C14 H14 111.00 . . . no C11 C14 H14 111.00 . . . no C13 C14 H14 111.00 . . . no C11 C15 H15A 108.00 . . . no C11 C15 H15B 108.00 . . . no C16 C15 H15A 108.00 . . . no C16 C15 H15B 108.00 . . . no H15A C15 H15B 107.00 . . . no C16 C17 H17A 109.00 . . . no C16 C17 H17B 109.00 . . . no C16 C17 H17C 109.00 . . . no H17A C17 H17B 110.00 . . . no H17A C17 H17C 110.00 . . . no H17B C17 H17C 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 C8 O2 C1 O1 2.5(3) . . . . no C8 O2 C1 C2 -177.82(15) . . . . no C1 O2 C8 C9 -157.17(16) . . . . no C11 O3 C10 C9 -36.31(18) . . . . no C10 O3 C11 O4 -91.71(17) . . . . no C10 O3 C11 C14 22.81(19) . . . . no C10 O3 C11 C15 151.97(15) . . . . no C12 O4 C11 O3 123.27(16) . . . . no C12 O4 C11 C14 7.3(2) . . . . no C12 O4 C11 C15 -119.96(17) . . . . no C11 O4 C12 O5 174.76(18) . . . . no C11 O4 C12 C13 -6.8(2) . . . . no O1 C1 C2 C3 171.9(2) . . . . no O1 C1 C2 C7 -8.1(3) . . . . no O2 C1 C2 C3 -7.8(3) . . . . no O2 C1 C2 C7 172.24(17) . . . . no C1 C2 C3 C4 -178.97(19) . . . . no C7 C2 C3 C4 1.0(3) . . . . no C1 C2 C7 C6 179.6(2) . . . . no C3 C2 C7 C6 -0.3(3) . . . . no C2 C3 C4 C5 -0.8(3) . . . . no C3 C4 C5 C6 0.0(3) . . . . no C4 C5 C6 C7 0.6(4) . . . . no C5 C6 C7 C2 -0.5(4) . . . . no O2 C8 C9 C10 -67.7(2) . . . . no O2 C8 C9 C14 178.40(15) . . . . no C8 C9 C10 O3 -84.02(18) . . . . no C14 C9 C10 O3 34.04(18) . . . . no C8 C9 C14 C11 100.04(17) . . . . no C8 C9 C14 C13 -146.47(16) . . . . no C10 C9 C14 C11 -20.16(18) . . . . no C10 C9 C14 C13 93.33(18) . . . . no O3 C11 C14 C9 -0.62(19) . . . . no O3 C11 C14 C13 -121.35(16) . . . . no O4 C11 C14 C9 115.95(16) . . . . no O4 C11 C14 C13 -4.79(18) . . . . no C15 C11 C14 C9 -123.74(18) . . . . no C15 C11 C14 C13 115.53(18) . . . . no O3 C11 C15 C16 -176.97(16) . . . . no O4 C11 C15 C16 65.7(2) . . . . no C14 C11 C15 C16 -53.8(2) . . . . no O4 C12 C13 C14 3.3(2) . . . . no O5 C12 C13 C14 -178.35(19) . . . . no C12 C13 C14 C9 -111.52(17) . . . . no C12 C13 C14 C11 1.15(19) . . . . no C11 C15 C16 O6 -2.0(3) . . . . no C11 C15 C16 C17 177.43(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 O1 C9 3.281(2) . 1_565 no O1 C10 3.371(3) . 1_565 no O3 C8 3.420(2) . 2_546 no O4 O6 2.946(2) . . no O5 C16 3.114(2) . 1_545 no O5 C17 3.417(3) . 1_545 no O5 C15 3.204(2) . 1_545 no O6 C12 2.999(2) . . no O6 O4 2.946(2) . . no O6 C17 3.322(3) . 2_547 no O6 C14 2.991(2) . . no O6 C13 3.077(2) . . no O1 H10B 2.7000 . 1_565 no O1 H13A 2.6400 . 1_565 no O1 H9 2.5100 . 1_565 no O1 H8B 2.3700 . . no O1 H9 2.7900 . 2_656 no O1 H7 2.5300 . . no O2 H10A 2.5900 . . no O2 H3 2.4500 . . no O3 H10B 2.7500 . 2_556 no O3 H8A 2.6200 . 2_546 no O3 H8A 2.8200 . . no O4 H10A 2.7100 . 2_546 no O5 H15A 2.5900 . 1_545 no O5 H5 2.7600 . 1_546 no O5 H14 2.6000 . 1_545 no O6 H13B 2.8100 . . no O6 H14 2.7000 . . no O6 H4 2.6100 . 1_556 no C2 C13 3.506(3) . 2_656 no C3 C13 3.543(3) . 2_656 no C8 O3 3.420(2) . 2_556 no C9 O1 3.281(2) . 1_545 no C10 C12 3.563(3) . . no C10 O1 3.371(3) . 1_545 no C12 C10 3.563(3) . . no C12 O6 2.999(2) . . no C12 C16 3.538(3) . . no C13 C3 3.543(3) . 2_646 no C13 C2 3.506(3) . 2_646 no C13 O6 3.077(2) . . no C14 O6 2.991(2) . . no C15 O5 3.204(2) . 1_565 no C16 O5 3.114(2) . 1_565 no C16 C12 3.538(3) . . no C16 C17 3.548(3) . 2_547 no C17 O6 3.322(3) . 2_557 no C17 C16 3.548(3) . 2_557 no C17 O5 3.417(3) . 1_565 no C1 H15B 2.9900 . 2_556 no C1 H9 3.0300 . 2_656 no C2 H15B 2.8200 . 2_556 no C3 H15B 3.0200 . 2_556 no C3 H13B 2.9500 . 2_656 no C4 H17A 2.8400 . 1_554 no C4 H13B 2.9800 . 2_656 no C10 H15A 3.0400 . 2_546 no C11 H8A 3.0900 . . no C16 H4 3.0800 . 1_556 no C16 H14 2.8700 . . no C17 H17A 2.9300 . 2_547 no C17 H17B 2.8500 . 2_557 no H3 O2 2.4500 . . no H4 O6 2.6100 . 1_554 no H4 C16 3.0800 . 1_554 no H4 H17A 2.5200 . 1_554 no H5 O5 2.7600 . 1_564 no H7 O1 2.5300 . . no H7 H8B 2.5100 . 2_656 no H8A O3 2.8200 . . no H8A C11 3.0900 . . no H8A H14 2.6000 . . no H8A O3 2.6200 . 2_556 no H8B O1 2.3700 . . no H8B H14 2.3600 . . no H8B H7 2.5100 . 2_646 no H9 O1 2.5100 . 1_545 no H9 H13A 2.2400 . . no H9 O1 2.7900 . 2_646 no H9 C1 3.0300 . 2_646 no H10A O2 2.5900 . . no H10A O4 2.7100 . 2_556 no H10B O1 2.7000 . 1_545 no H10B O3 2.7500 . 2_546 no H13A O1 2.6400 . 1_545 no H13A H9 2.2400 . . no H13B O6 2.8100 . . no H13B C3 2.9500 . 2_646 no H13B C4 2.9800 . 2_646 no H14 O5 2.6000 . 1_565 no H14 O6 2.7000 . . no H14 C16 2.8700 . . no H14 H8A 2.6000 . . no H14 H8B 2.3600 . . no H15A O5 2.5900 . 1_565 no H15A H17C 2.4300 . . no H15A C10 3.0400 . 2_556 no H15B H17C 2.4900 . . no H15B C1 2.9900 . 2_546 no H15B C2 2.8200 . 2_546 no H15B C3 3.0200 . 2_546 no H17A C4 2.8400 . 1_556 no H17A H4 2.5200 . 1_556 no H17A C17 2.9300 . 2_557 no H17A H17B 2.1200 . 2_557 no H17B C17 2.8500 . 2_547 no H17B H17A 2.1200 . 2_547 no H17C H15A 2.4300 . . no H17C H15B 2.4900 . . 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 C9 H9 O1 1.0000 2.5100 3.281(2) 133.00 1_545 yes C10 H10A O2 0.9900 2.5900 2.980(2) 103.00 . yes C14 H14 O5 1.0000 2.6000 3.458(2) 144.00 1_565 yes C15 H15A O5 0.9900 2.5900 3.204(2) 120.00 1_565 yes #===END # Attachment '- compound_3.cif' # CIF-file generated for Harrar 7.169 #============================================================================== data_k021 _database_code_depnum_ccdc_archive 'CCDC 861133' #TrackingRef '- compound_3.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 Cl N, C7 H7 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 'C15 H18 Cl N O5' _chemical_formula_iupac ? _chemical_formula_weight 327.75 _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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 6.6331(4) _cell_length_b 15.380(1) _cell_length_c 15.6364(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1595.18(17) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 3278 _cell_measurement_theta_min 4.0170 _cell_measurement_theta_max 74.9925 _cell_special_details ; ; _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5084 _exptl_crystal_size_mid 0.0431 _exptl_crystal_size_min 0.0264 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.330 _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 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 0.589 _exptl_absorpt_correction_T_max 0.943 #=============================================================================== # 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 '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 11839 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 75.50 _diffrn_reflns_theta_full 75.50 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3283 # number of observed reflections (> n sig(I)) _reflns_number_gt 2637 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 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^)+(0.1323P)^2^+0.5222P] 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 -0.04(4) # 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 ? _refine_ls_number_reflns 3283 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2274 _refine_ls_wR_factor_gt 0.2097 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.507 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.076 #=============================================================================== # 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 Cl1 Cl Uani 0.5443(2) 0.16150(9) 0.23413(9) 1.000 0.0708(4) . . N1 N Uani 0.8548(5) -0.1868(2) 0.4550(3) 1.000 0.0488(10) . . C1 C Uani 0.6248(7) 0.0609(3) 0.2725(3) 1.000 0.0503(12) . . C2 C Uani 0.4995(7) -0.0091(3) 0.2635(3) 1.000 0.0537(12) . . C3 C Uani 0.5650(8) -0.0887(3) 0.2933(3) 1.000 0.0533(14) . . C4 C Uani 0.7539(7) -0.0968(3) 0.3310(3) 1.000 0.0453(12) . . C5 C Uani 0.8742(6) -0.0256(3) 0.3389(3) 1.000 0.0458(11) . . C6 C Uani 0.8114(7) 0.0556(3) 0.3098(3) 1.000 0.0477(12) . . C7 C Uani 0.8192(8) -0.1865(3) 0.3612(3) 1.000 0.0550(15) . . C8 C Uani 1.0098(14) -0.2183(4) 0.3182(5) 1.000 0.096(3) . . O1 O Uani 0.4274(8) 0.3086(3) 0.5187(4) 1.000 0.097(2) . . O2 O Uani 0.3213(6) 0.1989(3) 0.5980(2) 1.000 0.0663(12) . . O3 O Uani 0.3863(6) 0.0575(3) 0.6426(2) 1.000 0.0662(13) . . O4 O Uani 0.1760(5) -0.0854(2) 0.5021(3) 1.000 0.0752(16) . . O5 O Uani 0.4752(5) -0.1465(2) 0.5129(3) 1.000 0.0666(13) . . C9 C Uani 0.3916(9) 0.2323(3) 0.5254(4) 1.000 0.0700(19) . . C10 C Uani 0.4045(11) 0.1629(3) 0.4568(4) 1.000 0.0690(18) . . C11 C Uani 0.3177(8) 0.0823(3) 0.4968(3) 1.000 0.0530(12) . . C12 C Uani 0.2720(8) 0.1082(3) 0.5889(3) 1.000 0.0573(16) . . C13 C Uani 0.5566(8) 0.0262(4) 0.5927(4) 1.000 0.0643(16) . . C14 C Uani 0.4637(7) 0.0062(3) 0.5067(3) 1.000 0.0503(12) . . C15 C Uani 0.3618(6) -0.0829(3) 0.5067(3) 1.000 0.0453(11) . . H1N H Uiso 0.87280 -0.24250 0.47320 1.000 0.0730 calc R H1O H Uiso 0.74660 -0.16310 0.48210 1.000 0.0730 calc R H1P H Uiso 0.96700 -0.15500 0.46700 1.000 0.0730 calc R H2 H Uiso 0.37080 -0.00310 0.23750 1.000 0.0650 calc R H3 H Uiso 0.48040 -0.13820 0.28810 1.000 0.0640 calc R H5 H Uiso 1.00320 -0.03140 0.36470 1.000 0.0550 calc R H6 H Uiso 0.89480 0.10540 0.31570 1.000 0.0570 calc R H7 H Uiso 0.70840 -0.22860 0.34820 1.000 0.0660 calc R H8A H Uiso 0.98680 -0.22340 0.25650 1.000 0.1440 calc R H8B H Uiso 1.11910 -0.17670 0.32870 1.000 0.1440 calc R H8C H Uiso 1.04700 -0.27520 0.34160 1.000 0.1440 calc R H10A H Uiso 0.32570 0.18000 0.40580 1.000 0.0830 calc R H10B H Uiso 0.54630 0.15310 0.43960 1.000 0.0830 calc R H11 H Uiso 0.19220 0.06370 0.46650 1.000 0.0640 calc R H12 H Uiso 0.12560 0.09900 0.60120 1.000 0.0690 calc R H13A H Uiso 0.61580 -0.02660 0.61880 1.000 0.0770 calc R H13B H Uiso 0.66230 0.07130 0.58770 1.000 0.0770 calc R H14 H Uiso 0.56910 0.00860 0.46100 1.000 0.0600 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 Cl1 0.0797(8) 0.0583(7) 0.0745(8) 0.0171(6) -0.0106(6) 0.0154(6) N1 0.0351(16) 0.0352(16) 0.076(2) 0.0140(16) 0.0000(16) -0.0012(13) C1 0.055(2) 0.051(2) 0.045(2) 0.0036(18) -0.0053(18) 0.0090(19) C2 0.049(2) 0.056(2) 0.056(2) -0.003(2) -0.012(2) 0.0050(18) C3 0.052(2) 0.048(2) 0.060(3) -0.0082(19) -0.010(2) -0.006(2) C4 0.050(2) 0.038(2) 0.048(2) -0.0029(16) -0.0025(16) 0.0001(17) C5 0.0364(19) 0.045(2) 0.056(2) 0.0040(18) -0.0052(16) 0.0007(16) C6 0.046(2) 0.045(2) 0.052(2) 0.0013(18) 0.0001(18) -0.0027(18) C7 0.063(3) 0.0341(19) 0.068(3) -0.0033(19) -0.001(2) 0.002(2) C8 0.136(7) 0.063(4) 0.089(4) 0.008(3) 0.037(5) 0.040(4) O1 0.092(3) 0.048(2) 0.152(5) -0.024(2) 0.053(3) -0.017(2) O2 0.067(2) 0.065(2) 0.067(2) -0.0147(17) 0.0020(19) -0.0039(18) O3 0.067(2) 0.083(3) 0.0485(17) 0.0051(17) 0.0026(15) 0.0093(19) O4 0.0395(16) 0.0520(18) 0.134(4) 0.007(2) -0.022(2) -0.0022(14) O5 0.0440(16) 0.0499(18) 0.106(3) 0.0254(18) 0.0139(18) 0.0070(13) C9 0.068(3) 0.049(3) 0.093(4) -0.012(3) 0.017(3) -0.009(2) C10 0.096(4) 0.045(2) 0.066(3) -0.003(2) 0.020(3) 0.001(3) C11 0.059(2) 0.043(2) 0.057(2) -0.0006(19) -0.002(2) -0.004(2) C12 0.051(2) 0.059(3) 0.062(3) 0.001(2) 0.002(2) -0.002(2) C13 0.042(2) 0.077(3) 0.074(3) 0.000(3) -0.008(2) -0.006(2) C14 0.045(2) 0.053(2) 0.053(2) 0.0007(18) 0.0043(19) -0.0049(19) C15 0.0390(19) 0.0409(19) 0.056(2) 0.0078(18) -0.0026(17) -0.0018(16) _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 Cl1 C1 1.743(5) . . yes O1 C9 1.202(7) . . yes O2 C12 1.440(7) . . yes O2 C9 1.330(7) . . yes O3 C12 1.374(6) . . yes O3 C13 1.455(7) . . yes O4 C15 1.235(5) . . yes O5 C15 1.238(5) . . yes N1 C7 1.486(7) . . yes N1 H1O 0.9100 . . no N1 H1P 0.9100 . . no N1 H1N 0.9100 . . no C1 C2 1.367(7) . . no C1 C6 1.371(7) . . no C2 C3 1.380(7) . . no C3 C4 1.390(7) . . no C4 C5 1.361(6) . . no C4 C7 1.521(7) . . no C5 C6 1.393(7) . . no C7 C8 1.513(10) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 1.0000 . . no C8 H8A 0.9800 . . no C8 H8B 0.9800 . . no C8 H8C 0.9800 . . no C9 C10 1.516(8) . . no C10 C11 1.503(7) . . no C11 C12 1.525(7) . . no C11 C14 1.527(7) . . no C13 C14 1.511(8) . . no C14 C15 1.528(6) . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C11 H11 1.0000 . . no C12 H12 1.0000 . . no C13 H13A 0.9900 . . no C13 H13B 0.9900 . . no C14 H14 1.0000 . . 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 C9 O2 C12 111.7(4) . . . yes C12 O3 C13 106.8(4) . . . yes H1N N1 H1O 110.00 . . . no C7 N1 H1P 109.00 . . . no C7 N1 H1O 109.00 . . . no H1N N1 H1P 110.00 . . . no H1O N1 H1P 109.00 . . . no C7 N1 H1N 109.00 . . . no Cl1 C1 C2 118.5(4) . . . yes Cl1 C1 C6 118.4(4) . . . yes C2 C1 C6 123.1(4) . . . no C1 C2 C3 118.2(4) . . . no C2 C3 C4 120.4(4) . . . no C3 C4 C7 118.0(4) . . . no C5 C4 C7 122.3(4) . . . no C3 C4 C5 119.7(4) . . . no C4 C5 C6 121.1(4) . . . no C1 C6 C5 117.5(4) . . . no N1 C7 C4 110.8(4) . . . yes C4 C7 C8 113.2(4) . . . no N1 C7 C8 107.8(5) . . . yes C3 C2 H2 121.00 . . . no C1 C2 H2 121.00 . . . no C4 C3 H3 120.00 . . . no C2 C3 H3 120.00 . . . no C6 C5 H5 119.00 . . . no C4 C5 H5 119.00 . . . no C1 C6 H6 121.00 . . . no C5 C6 H6 121.00 . . . no C4 C7 H7 108.00 . . . no N1 C7 H7 108.00 . . . no C8 C7 H7 108.00 . . . no C7 C8 H8B 109.00 . . . no C7 C8 H8C 109.00 . . . no H8A C8 H8C 110.00 . . . no H8B C8 H8C 110.00 . . . no H8A C8 H8B 109.00 . . . no C7 C8 H8A 109.00 . . . no O1 C9 O2 121.4(6) . . . yes O1 C9 C10 127.9(6) . . . yes O2 C9 C10 110.6(4) . . . yes C9 C10 C11 105.4(5) . . . no C10 C11 C12 104.7(4) . . . no C10 C11 C14 115.6(5) . . . no C12 C11 C14 103.3(4) . . . no O2 C12 O3 111.4(4) . . . yes O2 C12 C11 107.5(4) . . . yes O3 C12 C11 108.6(4) . . . yes O3 C13 C14 103.2(4) . . . yes C11 C14 C13 101.1(4) . . . no C11 C14 C15 114.0(4) . . . no C13 C14 C15 111.3(4) . . . no O4 C15 O5 125.9(4) . . . yes O4 C15 C14 118.0(4) . . . yes O5 C15 C14 116.1(4) . . . yes C9 C10 H10A 111.00 . . . no C9 C10 H10B 111.00 . . . no C11 C10 H10A 111.00 . . . no C11 C10 H10B 111.00 . . . no H10A C10 H10B 109.00 . . . no C10 C11 H11 111.00 . . . no C12 C11 H11 111.00 . . . no C14 C11 H11 111.00 . . . no O2 C12 H12 110.00 . . . no O3 C12 H12 110.00 . . . no C11 C12 H12 110.00 . . . no O3 C13 H13A 111.00 . . . no O3 C13 H13B 111.00 . . . no C14 C13 H13A 111.00 . . . no C14 C13 H13B 111.00 . . . no H13A C13 H13B 109.00 . . . no C11 C14 H14 110.00 . . . no C13 C14 H14 110.00 . . . no C15 C14 H14 110.00 . . . 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 C12 O2 C9 C10 -2.1(6) . . . . no C9 O2 C12 C11 -0.4(6) . . . . no C9 O2 C12 O3 118.5(5) . . . . no C12 O2 C9 O1 174.6(6) . . . . no C13 O3 C12 O2 -95.9(5) . . . . no C12 O3 C13 C14 -39.5(5) . . . . no C13 O3 C12 C11 22.3(5) . . . . no C6 C1 C2 C3 -0.2(7) . . . . no C2 C1 C6 C5 0.5(7) . . . . no Cl1 C1 C2 C3 179.4(4) . . . . no Cl1 C1 C6 C5 -179.1(4) . . . . no C1 C2 C3 C4 -0.3(7) . . . . no C2 C3 C4 C5 0.4(7) . . . . no C2 C3 C4 C7 -179.0(4) . . . . no C5 C4 C7 N1 62.1(6) . . . . no C3 C4 C5 C6 0.0(7) . . . . no C5 C4 C7 C8 -59.0(7) . . . . no C3 C4 C7 C8 120.3(6) . . . . no C7 C4 C5 C6 179.3(4) . . . . no C3 C4 C7 N1 -118.6(5) . . . . no C4 C5 C6 C1 -0.4(7) . . . . no O2 C9 C10 C11 3.7(7) . . . . no O1 C9 C10 C11 -172.7(6) . . . . no C9 C10 C11 C14 -116.6(5) . . . . no C9 C10 C11 C12 -3.7(6) . . . . no C10 C11 C12 O2 2.7(6) . . . . no C12 C11 C14 C13 -26.1(5) . . . . no C12 C11 C14 C15 93.4(5) . . . . no C10 C11 C12 O3 -118.0(5) . . . . no C14 C11 C12 O2 124.0(4) . . . . no C14 C11 C12 O3 3.4(5) . . . . no C10 C11 C14 C13 87.6(5) . . . . no C10 C11 C14 C15 -152.9(4) . . . . no O3 C13 C14 C11 39.6(5) . . . . no O3 C13 C14 C15 -81.8(5) . . . . no C11 C14 C15 O4 -2.6(6) . . . . no C11 C14 C15 O5 178.6(4) . . . . no C13 C14 C15 O4 111.0(5) . . . . no C13 C14 C15 O5 -67.8(6) . . . . 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 Cl1 C10 3.603(6) . . no Cl1 C8 3.583(9) . 4_755 no Cl1 H10A 3.0600 . . no Cl1 H3 3.1000 . 4_655 no Cl1 H7 2.7100 . 4_655 no Cl1 H8C 3.1100 . 4_755 no O1 C12 3.113(7) . 3_556 no O1 C11 3.095(7) . 3_556 no O1 O2 3.189(7) . 3_556 no O1 C9 3.217(8) . 3_556 no O1 C10 3.218(9) . 3_556 no O2 O1 3.189(7) . 3_456 no O3 C2 3.268(6) . 2_555 no O4 C5 3.371(6) . 1_455 no O4 N1 2.741(5) . 1_455 no O4 C12 3.334(6) . . no O5 N1 2.747(5) . . no O5 C7 3.348(6) . . no O5 C7 3.398(6) . 3_446 no O5 N1 2.732(4) . 3_446 no O5 C8 3.369(8) . 3_446 no O1 H11 2.6500 . 3_556 no O1 H10B 2.6800 . 3_456 no O1 H6 2.9200 . 3_456 no O1 H12 2.6900 . 3_556 no O1 H10A 2.9000 . 3_556 no O2 H8A 2.8100 . 2_655 no O3 H2 2.4100 . 2_555 no O4 H1P 1.8400 . 1_455 no O4 H11 2.3600 . . no O4 H5 2.5700 . 1_455 no O5 H13A 2.6500 . . no O5 H1N 1.8500 . 3_446 no O5 H1O 1.8800 . . no O5 H8C 2.6200 . 3_446 no N1 O4 2.741(5) . 1_655 no N1 O5 2.747(5) . . no N1 O5 2.732(4) . 3_546 no N1 H5 2.9500 . . no C1 C10 3.592(8) . . no C2 O3 3.268(6) . 2_554 no C3 C15 3.600(7) . . no C5 O4 3.371(6) . 1_655 no C7 O5 3.348(6) . . no C7 O5 3.398(6) . 3_546 no C8 O5 3.369(8) . 3_546 no C8 Cl1 3.583(9) . 4_745 no C9 C9 3.454(8) . 3_456 no C9 C13 3.515(8) . . no C9 C9 3.454(8) . 3_556 no C9 O1 3.217(8) . 3_456 no C10 Cl1 3.603(6) . . no C10 C1 3.592(8) . . no C10 O1 3.218(9) . 3_456 no C11 O1 3.095(7) . 3_456 no C12 O4 3.334(6) . . no C12 O1 3.113(7) . 3_456 no C13 C9 3.515(8) . . no C15 C3 3.600(7) . . no C1 H10B 3.0200 . . no C1 H13A 3.0000 . 2_654 no C1 H14 3.0800 . . no C2 H12 3.0100 . 2_554 no C3 H14 3.0200 . . no C4 H14 2.8700 . . no C5 H8B 2.8400 . . no C5 H1P 2.8900 . . no C5 H14 2.8300 . . no C6 H14 2.9500 . . no C6 H10B 3.0800 . . no C6 H13A 3.0600 . 2_654 no C8 H5 2.9700 . . no C9 H10B 2.9400 . 3_456 no C10 H13B 3.0200 . . no C12 H2 2.9800 . 2_555 no C13 H10B 3.0900 . . no C15 H1P 2.9100 . 1_455 no C15 H1O 2.8600 . . no C15 H1N 2.7000 . 3_446 no H1N H8C 2.4100 . . no H1N O5 1.8500 . 3_546 no H1N C15 2.7000 . 3_546 no H1O O5 1.8800 . . no H1O C15 2.8600 . . no H1P O4 1.8400 . 1_655 no H1P C5 2.8900 . . no H1P C15 2.9100 . 1_655 no H1P H5 2.5000 . . no H1P H8B 2.4100 . . no H2 O3 2.4100 . 2_554 no H2 C12 2.9800 . 2_554 no H2 H12 2.5900 . 2_554 no H3 H7 2.2600 . . no H3 H8B 2.5500 . 1_455 no H3 Cl1 3.1000 . 4_645 no H5 C8 2.9700 . . no H5 H1P 2.5000 . . no H5 H8B 2.4300 . . no H5 H11 2.5000 . 1_655 no H5 O4 2.5700 . 1_655 no H5 N1 2.9500 . . no H6 O1 2.9200 . 3_556 no H7 H3 2.2600 . . no H7 Cl1 2.7100 . 4_645 no H8A O2 2.8100 . 2_654 no H8B H3 2.5500 . 1_655 no H8B H5 2.4300 . . no H8B C5 2.8400 . . no H8B H1P 2.4100 . . no H8C Cl1 3.1100 . 4_745 no H8C H1N 2.4100 . . no H8C O5 2.6200 . 3_546 no H10A Cl1 3.0600 . . no H10A O1 2.9000 . 3_456 no H10B C1 3.0200 . . no H10B C6 3.0800 . . no H10B C13 3.0900 . . no H10B H14 2.2500 . . no H10B O1 2.6800 . 3_556 no H10B C9 2.9400 . 3_556 no H11 O4 2.3600 . . no H11 H5 2.5000 . 1_455 no H11 O1 2.6500 . 3_456 no H12 C2 3.0100 . 2_555 no H12 H2 2.5900 . 2_555 no H12 O1 2.6900 . 3_456 no H13A O5 2.6500 . . no H13A C1 3.0000 . 2_655 no H13A C6 3.0600 . 2_655 no H13B C10 3.0200 . . no H14 C1 3.0800 . . no H14 C3 3.0200 . . no H14 C4 2.8700 . . no H14 C5 2.8300 . . no H14 C6 2.9500 . . no H14 H10B 2.2500 . . 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 N1 H1N O5 0.9100 1.8500 2.732(4) 162.00 3_546 yes N1 H1O O5 0.9100 1.8800 2.747(5) 158.00 . yes N1 H1P O4 0.9100 1.8400 2.741(5) 173.00 1_655 yes C2 H2 O3 0.9500 2.4100 3.268(6) 150.00 2_554 yes C5 H5 O4 0.9500 2.5700 3.371(6) 142.00 1_655 yes C7 H7 Cl1 1.0000 2.7100 3.674(5) 163.00 4_645 yes C11 H11 O4 1.0000 2.3600 2.746(6) 102.00 . yes #===END # Attachment '- compound_12.cif' # CIF-file generated for Harrar 7.182 #============================================================================== data_k067 _database_code_depnum_ccdc_archive 'CCDC 861134' #TrackingRef '- compound_12.cif' _chemical_name_common ? #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_formula_iupac ? _chemical_formula_moiety 'C7 H8 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 'C7 H8 O5' _chemical_formula_weight 172.13 _chemical_compound_source 'see text' _chemical_melting_point ? 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _symmetry_cell_setting Monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _cell_length_a 5.39904(17) _cell_length_b 14.8577(4) _cell_length_c 8.6593(3) _cell_angle_alpha 90 _cell_angle_beta 103.704(3) _cell_angle_gamma 90 _cell_volume 674.85(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1663 _cell_measurement_temperature 123 _cell_measurement_theta_max 75.5879 _cell_measurement_theta_min 2.9718 _cell_special_details ; ; _exptl_absorpt_coefficient_mu 1.277 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_correction_T_min 0.910 # 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 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_crystal_colour colourless _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_meas ? _exptl_crystal_density_meas_temp ? _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.1337 _exptl_crystal_size_mid 0.0766 _exptl_crystal_size_min 0.0487 _exptl_crystal_size_rad ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -9 # number of measured reflections (redundant set) _diffrn_reflns_number 2478 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 75.77 _diffrn_reflns_theta_max 75.77 _diffrn_reflns_theta_min 5.96 _diffrn_ambient_temperature 123 _diffrn_detector_area_resol_mean 10.3546 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 # number of observed reflections (> n sig(I)) _reflns_number_gt 1247 # number of unique reflections _reflns_number_total 1379 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) ; _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _refine_diff_density_max 0.313 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.067 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 # 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 ref _refine_ls_matrix_type full _refine_ls_number_constraints ? _refine_ls_number_parameters 112 _refine_ls_number_reflns 1379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0444 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.2700P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1187 _refine_ls_wR_factor_ref 0.1250 #=============================================================================== # 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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap #=============================================================================== # 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 H1 H Uiso -0.04060 0.34700 0.39630 1.000 0.0190 calc R H2A H Uiso 0.44620 0.42540 0.39970 1.000 0.0230 calc R H2B H Uiso 0.36090 0.37580 0.54420 1.000 0.0230 calc R H3 H Uiso 0.23750 0.20250 0.22800 1.000 0.0190 calc R H4 H Uiso -0.09410 0.29640 0.14090 1.000 0.0180 calc R H5A H Uiso -0.01330 0.39020 -0.04480 1.000 0.0200 calc R H5B H Uiso 0.17480 0.45050 0.08730 1.000 0.0200 calc R H5O H Uiso -0.315(5) 0.5365(18) 0.202(3) 1.000 0.0250 . . C1 C Uani 0.0681(3) 0.38052(11) 0.33702(17) 1.000 0.0163(4) . . C2 C Uani 0.3466(3) 0.37462(11) 0.42812(18) 1.000 0.0195(4) . . C3 C Uani 0.2972(3) 0.26628(10) 0.22916(18) 1.000 0.0156(4) . . C4 C Uani 0.0683(3) 0.33044(10) 0.18065(17) 1.000 0.0149(4) . . C5 C Uani 0.1324(3) 0.38828(11) 0.04929(17) 1.000 0.0164(4) . . C6 C Uani 0.3587(3) 0.34357(10) 0.00906(18) 1.000 0.0161(4) . . C7 C Uani -0.0291(3) 0.47575(10) 0.30728(17) 1.000 0.0160(4) . . O1 O Uani 0.4366(2) 0.28968(8) 0.38035(13) 1.000 0.0193(3) . . O2 O Uani 0.4524(2) 0.27869(8) 0.11306(13) 1.000 0.0170(3) . . O3 O Uani 0.4550(2) 0.36134(9) -0.10044(14) 1.000 0.0211(3) . . O4 O Uani 0.0968(2) 0.54270(8) 0.34702(14) 1.000 0.0237(3) . . O5 O Uani -0.2719(2) 0.47816(8) 0.22598(14) 1.000 0.0211(3) . . 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 C1 0.0185(7) 0.0168(8) 0.0149(7) 0.0007(5) 0.0068(5) -0.0003(5) C2 0.0217(8) 0.0203(8) 0.0158(7) -0.0016(6) 0.0033(6) 0.0013(6) C3 0.0155(7) 0.0168(7) 0.0149(7) 0.0012(5) 0.0046(5) 0.0003(5) C4 0.0148(7) 0.0142(7) 0.0165(7) -0.0011(5) 0.0052(5) 0.0007(5) C5 0.0181(7) 0.0162(7) 0.0156(7) 0.0001(5) 0.0056(5) 0.0031(5) C6 0.0170(7) 0.0157(7) 0.0153(7) -0.0015(5) 0.0033(5) 0.0007(5) C7 0.0208(7) 0.0180(7) 0.0116(7) -0.0004(5) 0.0088(5) 0.0009(6) O1 0.0207(6) 0.0204(6) 0.0155(6) 0.0005(4) 0.0019(4) 0.0048(4) O2 0.0164(5) 0.0182(6) 0.0178(6) 0.0021(4) 0.0066(4) 0.0033(4) O3 0.0231(6) 0.0243(6) 0.0190(6) 0.0037(4) 0.0112(4) 0.0046(4) O4 0.0268(6) 0.0179(6) 0.0251(6) -0.0012(5) 0.0036(5) -0.0015(5) O5 0.0198(6) 0.0190(6) 0.0243(6) 0.0012(4) 0.0051(4) 0.0018(4) _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 C1 H1 1.0000 . . no C1 C2 1.526(2) . . no C1 C4 1.545(2) . . no C1 C7 1.510(2) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C3 H3 1.0000 . . no C3 C4 1.538(2) . . no C4 H4 1.0000 . . no C4 C5 1.529(2) . . no C5 H5A 0.9900 . . no C5 H5B 0.9900 . . no C5 C6 1.502(2) . . no O1 C2 1.448(2) . . yes O1 C3 1.3909(19) . . yes O2 C3 1.4649(19) . . yes O2 C6 1.3343(19) . . yes O3 C6 1.214(2) . . yes O4 C7 1.2079(19) . . yes O5 H5O 0.91(3) . . no O5 C7 1.333(2) . . yes 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 C2 C1 H1 109.00 . . . no C2 C1 C4 102.72(13) . . . no C2 C1 C7 113.71(13) . . . no C4 C1 H1 109.00 . . . no C4 C1 C7 111.97(12) . . . no C7 C1 H1 109.00 . . . no H2A C2 H2B 109.00 . . . no C1 C2 H2A 111.00 . . . no C1 C2 H2B 111.00 . . . no O1 C2 H2A 111.00 . . . no O1 C2 H2B 111.00 . . . no O1 C2 C1 104.99(12) . . . yes C4 C3 H3 110.00 . . . no O1 C3 H3 110.00 . . . no O1 C3 C4 108.83(12) . . . yes O1 C3 O2 110.16(13) . . . yes O2 C3 H3 110.00 . . . no O2 C3 C4 106.72(12) . . . yes C1 C4 H4 111.00 . . . no C1 C4 C3 103.09(12) . . . no C1 C4 C5 115.37(13) . . . no C3 C4 H4 111.00 . . . no C3 C4 C5 104.04(13) . . . no C5 C4 H4 111.00 . . . no H5A C5 H5B 109.00 . . . no C4 C5 H5A 111.00 . . . no C4 C5 H5B 111.00 . . . no C4 C5 C6 105.29(13) . . . no C6 C5 H5A 111.00 . . . no C6 C5 H5B 111.00 . . . no O2 C6 C5 111.23(13) . . . yes O2 C6 O3 121.36(15) . . . yes O3 C6 C5 127.41(14) . . . yes O4 C7 C1 125.01(15) . . . yes O4 C7 O5 123.01(14) . . . yes O5 C7 C1 111.95(13) . . . yes C2 O1 C3 110.09(12) . . . yes C3 O2 C6 111.54(12) . . . yes C7 O5 H5O 108.2(17) . . . 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 H1 C6 3.0900 . 4_455 no H1 O2 2.6500 . 4_455 no H1 O4 2.8400 . 3_566 no H2A O4 2.5300 . . no H2A O5 2.5100 . 1_655 no H2B H3 2.5500 . 4_555 no H3 H2B 2.5500 . 4_454 no H3 H5A 2.5100 . 4_555 no H3 O3 2.5500 . 4_455 no H3 O4 2.6700 . 2_545 no H4 C6 2.9900 . 1_455 no H4 O1 2.6300 . 4_454 no H4 O2 2.4200 . 1_455 no H5A H3 2.5100 . 4_454 no H5A H5B 2.5200 . 3_565 no H5A C3 3.0600 . 4_454 no H5A C7 3.0700 . 3_565 no H5A O1 2.7500 . 4_454 no H5A O3 2.8300 . 1_455 no H5A O4 2.7400 . 3_565 no H5B H5A 2.5200 . 3_565 no H5B H5B 2.5800 . 3_565 no H5B C2 3.0900 . . no H5B C5 2.9900 . 3_565 no H5B C7 2.4400 . . no H5B O4 2.7500 . . no H5O C5 2.82(3) . 3_565 no H5O C6 2.52(3) . 3_565 no H5O O3 1.83(3) . 3_565 no C1 O4 3.2763(19) . 3_566 no C2 H5B 3.0900 . . no C2 O4 3.400(2) . 3_666 no C2 O5 3.374(2) . 1_655 no C3 H5A 3.0600 . 4_555 no C3 O1 3.2892(19) . 4_454 no C3 O3 3.237(2) . 4_455 no C4 O1 3.0946(18) . 4_454 no C4 O2 3.327(2) . 1_455 no C5 H5B 2.9900 . 3_565 no C5 H5O 2.82(3) . 3_565 no C5 O1 3.085(2) . 4_454 no C5 O5 3.236(2) . . no C5 O5 3.3223(19) . 3_565 no C6 H1 3.0900 . 4_554 no C6 H4 2.9900 . 1_655 no C6 H5O 2.52(3) . 3_565 no C6 O1 3.0252(19) . 4_454 no C6 O5 3.1193(19) . 1_655 no C6 O5 3.3054(19) . 3_565 no C7 H5A 3.0700 . 3_565 no C7 H5B 2.4400 . . no C7 C7 3.356(2) . 3_566 no C7 O4 3.1126(19) . 3_566 no O1 H4 2.6300 . 4_555 no O1 H5A 2.7500 . 4_555 no O1 C3 3.2892(19) . 4_555 no O1 C4 3.0946(18) . 4_555 no O1 C5 3.085(2) . 4_555 no O1 C6 3.0252(19) . 4_555 no O1 O2 3.1920(16) . 4_555 no O2 H1 2.6500 . 4_554 no O2 H4 2.4200 . 1_655 no O2 C4 3.327(2) . 1_655 no O2 O1 3.1920(16) . 4_454 no O3 H3 2.5500 . 4_554 no O3 H5A 2.8300 . 1_655 no O3 H5O 1.83(3) . 3_565 no O3 C3 3.237(2) . 4_554 no O3 O5 2.7086(18) . 3_565 no O4 H1 2.8400 . 3_566 no O4 H2A 2.5300 . . no O4 H3 2.6700 . 2_555 no O4 H5A 2.7400 . 3_565 no O4 H5B 2.7500 . . no O4 C1 3.2763(19) . 3_566 no O4 C2 3.400(2) . 3_666 no O4 C7 3.1126(19) . 3_566 no O5 H2A 2.5100 . 1_455 no O5 C2 3.374(2) . 1_455 no O5 C5 3.3223(19) . 3_565 no O5 C5 3.236(2) . . no O5 C6 3.3054(19) . 3_565 no O5 C6 3.1193(19) . 1_455 no O5 O3 2.7086(18) . 3_565 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 O5 0.9900 2.5100 3.374(2) 146.00 1_655 yes C3 H3 O3 1.0000 2.5500 3.237(2) 126.00 4_455 yes C4 H4 O2 1.0000 2.4200 3.327(2) 151.00 1_455 yes O5 H5O O3 0.91(3) 1.83(3) 2.7086(18) 163(2) 3_565 yes 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 C1 C4 C5 C6 122.83(14) . . . . no C2 C1 C4 C3 25.72(15) . . . . no C2 C1 C4 C5 -86.98(16) . . . . no C2 C1 C7 O4 1.4(2) . . . . no C2 C1 C7 O5 179.30(12) . . . . no C2 O1 C3 C4 -9.98(16) . . . . no C2 O1 C3 O2 106.70(13) . . . . no C3 C4 C5 C6 10.69(15) . . . . no C3 O1 C2 C1 27.00(16) . . . . no C3 O2 C6 C5 3.76(17) . . . . no C3 O2 C6 O3 -176.95(14) . . . . no C4 C1 C2 O1 -32.22(15) . . . . no C4 C1 C7 O4 -114.45(17) . . . . no C4 C1 C7 O5 63.42(17) . . . . no C4 C5 C6 O2 -9.39(17) . . . . no C4 C5 C6 O3 171.37(16) . . . . no C6 O2 C3 C4 3.47(16) . . . . no C6 O2 C3 O1 -114.52(14) . . . . no C7 C1 C2 O1 -153.42(12) . . . . no C7 C1 C4 C3 148.10(13) . . . . no C7 C1 C4 C5 35.40(19) . . . . no O1 C3 C4 C1 -10.77(16) . . . . no O1 C3 C4 C5 110.00(13) . . . . no O2 C3 C4 C1 -129.62(12) . . . . no O2 C3 C4 C5 -8.85(15) . . . . no