# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Martin, Schanderl' 'Won, Jeong' 'Micahel, Schwarz' 'Reiser, Oliver' _publ_contact_author_name 'Reiser, Oliver' _publ_contact_author_email Oliver.Reiser@chemie.uni-regensburg.de _publ_section_title ; Stereoselective Wagner-Meerwein Rearrangement of Guaianolides ; # Attachment '- 06.cif' # CIF-file generated for Schanderl Scm134 #============================================================================== data_i201 _database_code_depnum_ccdc_archive 'CCDC 798357' #TrackingRef '- 06.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H20 O4' _chemical_formula_iupac ? _chemical_formula_weight 264.31 _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 0.0106 0.0060 '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 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 5.6695(5) _cell_length_b 13.7791(13) _cell_length_c 18.0400(17) _cell_angle_alpha 90 _cell_angle_beta 95.532(11) _cell_angle_gamma 90 _cell_volume 1402.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297 _cell_measurement_reflns_used 7034 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 25.91 _cell_special_details ; Cell parameters were determined by indexing 7034 reflections with I/sigma limit 6.0. ; _exptl_crystal_description prism _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.090 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type none # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.982 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; Data were collected applying an imaging plate system (STOE) with the following measurement parameters: Detector distance [mm] 70 Phi movement mode Oscillation Phi incr. [degrees] 1.0 Number of exposures 360 Irradiation / exposure [min] 8.00 For a detailed description of the method see: Sheldrick, G.M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89-98. ; _diffrn_ambient_temperature 297(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 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 19944 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.91 _diffrn_reflns_theta_full 25.91 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 5396 # number of observed reflections (> n sig(I)) _reflns_number_gt 2515 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'STOE (1998)' _computing_cell_refinement 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0615P)^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 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 0.3(13) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration syn _refine_ls_number_reflns 5396 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1075 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.788 _refine_ls_restrained_S_all 0.788 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.161 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.033 #=============================================================================== # 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 -1.1080(5) -0.4638(2) -0.00332(18) 1.000 0.0854(11) . . O2 O Uani -1.3139(6) -0.4758(2) -0.1121(2) 1.000 0.1134(17) . . O3 O Uani -0.7437(5) -0.19222(18) -0.14426(13) 1.000 0.0694(10) . . O4 O Uani -0.4019(6) -0.1911(3) -0.19507(14) 1.000 0.0960(13) . . C1 C Uani -1.1483(8) -0.4372(3) -0.0755(3) 1.000 0.0825(19) . . C2 C Uani -0.9831(7) -0.3680(3) -0.1074(2) 1.000 0.0745(14) . . C3 C Uani -0.8414(6) -0.3040(3) -0.05089(18) 1.000 0.0589(11) . . C4 C Uani -0.7409(6) -0.3679(2) 0.01310(19) 1.000 0.0568(11) . . C5 C Uani -0.9500(6) -0.4094(3) 0.0496(2) 1.000 0.0634(14) . . C6 C Uani -0.8789(8) -0.4728(3) 0.1160(2) 1.000 0.0789(16) . . C7 C Uani -0.7286(8) -0.4135(3) 0.1737(2) 1.000 0.0813(17) . . C8 C Uani -0.5097(7) -0.3736(3) 0.1408(2) 1.000 0.0776(16) . . C9 C Uani -0.5690(6) -0.3164(3) 0.07009(18) 1.000 0.0570(12) . . C10 C Uani -0.4718(6) -0.2318(3) 0.05396(18) 1.000 0.0586(12) . . C11 C Uani -0.5210(7) -0.1831(3) -0.02144(19) 1.000 0.0642(12) . . C12 C Uani -0.6404(6) -0.2492(3) -0.08084(18) 1.000 0.0598(12) . . C13 C Uani -0.2982(7) -0.1753(3) 0.1057(2) 1.000 0.0761(14) . . C14 C Uani -0.6063(7) -0.1691(3) -0.19788(19) 1.000 0.0629(14) . . C15 C Uani -0.7414(8) -0.1136(3) -0.25911(19) 1.000 0.0855(16) . . O5 O Uani -2.0704(5) -0.4704(2) -0.48172(16) 1.000 0.0806(11) . . O6 O Uani -2.2899(6) -0.4884(2) -0.58805(18) 1.000 0.1039(14) . . O7 O Uani -1.7363(5) -0.20532(18) -0.63752(12) 1.000 0.0687(10) . . O8 O Uani -1.4143(6) -0.2144(3) -0.69702(14) 1.000 0.1082(16) . . C16 C Uani -2.1235(8) -0.4473(3) -0.5541(3) 1.000 0.0756(16) . . C17 C Uani -1.9657(7) -0.3783(3) -0.5908(2) 1.000 0.0721(14) . . C18 C Uani -1.8176(6) -0.3115(3) -0.53894(17) 1.000 0.0542(11) . . C19 C Uani -1.7076(6) -0.3715(2) -0.47320(18) 1.000 0.0534(11) . . C20 C Uani -1.9087(6) -0.4114(3) -0.4331(2) 1.000 0.0606(12) . . C21 C Uani -1.8288(7) -0.4707(3) -0.3654(2) 1.000 0.0751(17) . . C22 C Uani -1.6768(7) -0.4062(3) -0.3110(2) 1.000 0.0759(16) . . C23 C Uani -1.4660(7) -0.3671(3) -0.34797(19) 1.000 0.0729(14) . . C24 C Uani -1.5327(6) -0.3157(3) -0.42037(18) 1.000 0.0541(11) . . C25 C Uani -1.4404(6) -0.2322(3) -0.44165(18) 1.000 0.0584(12) . . C26 C Uani -1.4982(7) -0.1890(3) -0.51820(19) 1.000 0.0645(12) . . C27 C Uani -1.6236(6) -0.2586(3) -0.57381(17) 1.000 0.0553(11) . . C28 C Uani -1.2680(7) -0.1712(3) -0.3929(2) 1.000 0.0750(16) . . C29 C Uani -1.6159(8) -0.1897(3) -0.69555(18) 1.000 0.0641(15) . . C30 C Uani -1.7563(8) -0.1366(3) -0.75575(18) 1.000 0.0810(15) . . H2A H Uiso -1.07430 -0.32660 -0.14300 1.000 0.0890 calc R H2B H Uiso -0.87330 -0.40470 -0.13440 1.000 0.0890 calc R H3 H Uiso -0.94940 -0.25680 -0.03160 1.000 0.0710 calc R H4 H Uiso -0.65660 -0.42190 -0.00780 1.000 0.0680 calc R H5 H Uiso -1.04010 -0.35460 0.06700 1.000 0.0760 calc R H6A H Uiso -0.78920 -0.52810 0.10090 1.000 0.0940 calc R H6B H Uiso -1.01900 -0.49670 0.13700 1.000 0.0940 calc R H7A H Uiso -0.67960 -0.45400 0.21650 1.000 0.0980 calc R H7B H Uiso -0.82170 -0.36020 0.19050 1.000 0.0980 calc R H8A H Uiso -0.42290 -0.33210 0.17740 1.000 0.0930 calc R H8B H Uiso -0.40700 -0.42720 0.13040 1.000 0.0930 calc R H11A H Uiso -0.62110 -0.12690 -0.01620 1.000 0.0770 calc R H11B H Uiso -0.37240 -0.16030 -0.03760 1.000 0.0770 calc R H12 H Uiso -0.52460 -0.29520 -0.09740 1.000 0.0720 calc R H13A H Uiso -0.36870 -0.16050 0.15070 1.000 0.0910 calc R H13B H Uiso -0.25740 -0.11610 0.08200 1.000 0.0910 calc R H13C H Uiso -0.15780 -0.21340 0.11750 1.000 0.0910 calc R H15A H Uiso -0.87160 -0.15220 -0.28050 1.000 0.1030 calc R H15B H Uiso -0.63860 -0.09820 -0.29670 1.000 0.1030 calc R H15C H Uiso -0.80080 -0.05470 -0.23950 1.000 0.1030 calc R H17A H Uiso -2.06380 -0.33890 -0.62610 1.000 0.0870 calc R H17B H Uiso -1.86020 -0.41590 -0.61890 1.000 0.0870 calc R H18 H Uiso -1.92290 -0.26310 -0.51980 1.000 0.0650 calc R H19 H Uiso -1.62360 -0.42640 -0.49310 1.000 0.0640 calc R H20 H Uiso -1.99890 -0.35600 -0.41660 1.000 0.0730 calc R H21A H Uiso -1.73740 -0.52610 -0.37950 1.000 0.0900 calc R H21B H Uiso -1.96520 -0.49440 -0.34230 1.000 0.0900 calc R H22A H Uiso -1.77120 -0.35260 -0.29540 1.000 0.0910 calc R H22B H Uiso -1.62100 -0.44350 -0.26720 1.000 0.0910 calc R H23A H Uiso -1.37860 -0.32260 -0.31390 1.000 0.0880 calc R H23B H Uiso -1.36130 -0.42070 -0.35690 1.000 0.0880 calc R H26A H Uiso -1.35220 -0.16760 -0.53700 1.000 0.0770 calc R H26B H Uiso -1.59740 -0.13230 -0.51400 1.000 0.0770 calc R H27 H Uiso -1.50980 -0.30540 -0.59060 1.000 0.0670 calc R H28A H Uiso -1.33940 -0.15210 -0.34900 1.000 0.0900 calc R H28B H Uiso -1.22750 -0.11430 -0.41970 1.000 0.0900 calc R H28C H Uiso -1.12730 -0.20820 -0.37880 1.000 0.0900 calc R H30A H Uiso -1.89630 -0.17300 -0.77180 1.000 0.0970 calc R H30B H Uiso -1.66310 -0.12780 -0.79690 1.000 0.0970 calc R H30C H Uiso -1.80080 -0.07430 -0.73760 1.000 0.0970 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 0.084(2) 0.0688(19) 0.107(2) -0.0102(18) 0.0277(17) -0.0258(16) O2 0.100(3) 0.101(3) 0.139(3) -0.041(2) 0.010(2) -0.035(2) O3 0.0661(16) 0.0787(19) 0.0651(14) 0.0140(13) 0.0148(13) 0.0079(14) O4 0.075(2) 0.138(3) 0.0768(18) 0.0183(17) 0.0167(16) 0.0002(19) C1 0.070(3) 0.067(3) 0.112(4) -0.028(3) 0.017(3) -0.009(2) C2 0.067(2) 0.079(3) 0.078(2) -0.009(2) 0.010(2) -0.006(2) C3 0.054(2) 0.061(2) 0.0634(19) -0.0063(18) 0.0145(17) 0.0023(19) C4 0.0544(19) 0.045(2) 0.074(2) -0.0016(18) 0.0224(18) 0.0037(17) C5 0.061(2) 0.046(2) 0.087(3) -0.005(2) 0.027(2) -0.001(2) C6 0.082(3) 0.056(2) 0.106(3) 0.010(2) 0.046(3) 0.009(2) C7 0.087(3) 0.079(3) 0.082(3) 0.023(2) 0.030(2) 0.019(3) C8 0.073(3) 0.082(3) 0.079(2) 0.016(2) 0.014(2) 0.013(2) C9 0.052(2) 0.058(2) 0.063(2) 0.0015(18) 0.0156(17) 0.0106(19) C10 0.056(2) 0.053(2) 0.067(2) 0.0011(18) 0.0072(17) 0.0058(19) C11 0.062(2) 0.063(2) 0.068(2) 0.0025(19) 0.008(2) -0.007(2) C12 0.054(2) 0.060(2) 0.067(2) 0.0064(19) 0.0144(17) 0.0071(19) C13 0.072(2) 0.078(3) 0.078(2) -0.006(2) 0.005(2) -0.002(2) C14 0.068(3) 0.067(2) 0.053(2) -0.0070(18) 0.002(2) -0.008(2) C15 0.102(3) 0.099(3) 0.054(2) -0.001(2) 0.000(2) -0.002(3) O5 0.086(2) 0.0723(19) 0.0863(19) -0.0013(17) 0.0225(15) -0.0188(16) O6 0.095(2) 0.102(3) 0.115(2) -0.033(2) 0.0117(19) -0.0358(19) O7 0.0688(16) 0.084(2) 0.0549(13) 0.0179(12) 0.0147(12) 0.0125(14) O8 0.082(2) 0.176(4) 0.0686(17) 0.0251(19) 0.0178(16) 0.014(2) C16 0.063(2) 0.065(3) 0.100(3) -0.024(2) 0.014(2) -0.015(2) C17 0.066(2) 0.083(3) 0.068(2) -0.003(2) 0.0101(19) -0.004(2) C18 0.0505(19) 0.053(2) 0.0610(19) -0.0088(17) 0.0156(17) 0.0032(18) C19 0.055(2) 0.046(2) 0.0624(19) 0.0045(17) 0.0217(17) 0.0043(17) C20 0.062(2) 0.052(2) 0.071(2) -0.0012(19) 0.0222(19) -0.007(2) C21 0.078(3) 0.063(3) 0.090(3) 0.019(2) 0.037(2) 0.005(2) C22 0.083(3) 0.079(3) 0.069(2) 0.016(2) 0.025(2) 0.019(2) C23 0.067(2) 0.088(3) 0.065(2) 0.018(2) 0.0129(18) 0.008(2) C24 0.0492(19) 0.057(2) 0.0577(19) 0.0007(17) 0.0135(16) 0.0055(18) C25 0.051(2) 0.059(2) 0.066(2) 0.0044(18) 0.0103(17) 0.0022(19) C26 0.064(2) 0.060(2) 0.071(2) 0.0048(19) 0.015(2) -0.005(2) C27 0.057(2) 0.057(2) 0.0529(19) 0.0078(16) 0.0104(16) 0.0032(18) C28 0.076(3) 0.069(3) 0.079(2) -0.008(2) 0.003(2) -0.005(2) C29 0.072(3) 0.071(3) 0.0486(19) -0.0063(17) 0.003(2) -0.006(2) C30 0.107(3) 0.082(3) 0.0516(19) 0.000(2) -0.004(2) 0.001(2) _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 1.351(6) . . yes O1 C5 1.453(5) . . yes O2 C1 1.217(6) . . yes O3 C12 1.463(4) . . yes O3 C14 1.338(5) . . yes O4 C14 1.194(5) . . yes O5 C16 1.350(6) . . yes O5 C20 1.455(5) . . yes O6 C16 1.214(6) . . yes O7 C27 1.458(4) . . yes O7 C29 1.321(4) . . yes O8 C29 1.195(6) . . yes C1 C2 1.491(6) . . no C2 C3 1.518(5) . . no C3 C12 1.510(5) . . no C3 C4 1.518(5) . . no C4 C5 1.522(5) . . no C4 C9 1.522(5) . . no C5 C6 1.506(5) . . no C6 C7 1.519(6) . . no C7 C8 1.529(6) . . no C8 C9 1.510(5) . . no C9 C10 1.334(6) . . no C10 C13 1.506(5) . . no C10 C11 1.518(5) . . no C11 C12 1.515(5) . . no C14 C15 1.493(5) . . no C2 H2A 0.9700 . . no C2 H2B 0.9700 . . no C3 H3 0.9800 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C6 H6B 0.9700 . . no C6 H6A 0.9700 . . no C7 H7A 0.9700 . . no C7 H7B 0.9700 . . no C8 H8B 0.9700 . . no C8 H8A 0.9700 . . no C11 H11B 0.9700 . . no C11 H11A 0.9700 . . no C12 H12 0.9800 . . no C13 H13B 0.9600 . . no C13 H13A 0.9600 . . no C13 H13C 0.9600 . . no C15 H15C 0.9600 . . no C15 H15A 0.9600 . . no C15 H15B 0.9600 . . no C16 C17 1.502(6) . . no C17 C18 1.509(5) . . no C18 C19 1.529(5) . . no C18 C27 1.507(5) . . no C19 C20 1.512(5) . . no C19 C24 1.517(5) . . no C20 C21 1.503(5) . . no C21 C22 1.527(5) . . no C22 C23 1.522(6) . . no C23 C24 1.502(5) . . no C24 C25 1.336(6) . . no C25 C26 1.511(5) . . no C25 C28 1.507(5) . . no C26 C27 1.515(5) . . no C29 C30 1.477(5) . . no C17 H17A 0.9700 . . no C17 H17B 0.9700 . . no C18 H18 0.9800 . . no C19 H19 0.9800 . . no C20 H20 0.9800 . . no C21 H21A 0.9700 . . no C21 H21B 0.9700 . . no C22 H22A 0.9700 . . no C22 H22B 0.9700 . . no C23 H23A 0.9700 . . no C23 H23B 0.9700 . . no C26 H26A 0.9700 . . no C26 H26B 0.9700 . . no C27 H27 0.9800 . . no C28 H28A 0.9600 . . no C28 H28B 0.9600 . . no C28 H28C 0.9600 . . no C30 H30A 0.9600 . . no C30 H30B 0.9600 . . no C30 H30C 0.9600 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 122.0(3) . . . yes C12 O3 C14 118.5(3) . . . yes C16 O5 C20 121.4(3) . . . yes C27 O7 C29 119.1(3) . . . yes O2 C1 C2 123.4(5) . . . yes O1 C1 C2 119.4(4) . . . yes O1 C1 O2 117.0(4) . . . yes C1 C2 C3 115.1(3) . . . no C2 C3 C4 108.0(3) . . . no C2 C3 C12 114.8(3) . . . no C4 C3 C12 108.7(3) . . . no C3 C4 C5 107.2(3) . . . no C5 C4 C9 111.0(3) . . . no C3 C4 C9 114.3(3) . . . no O1 C5 C6 108.9(3) . . . yes O1 C5 C4 111.5(3) . . . yes C4 C5 C6 113.7(3) . . . no C5 C6 C7 108.8(3) . . . no C6 C7 C8 110.5(3) . . . no C7 C8 C9 113.1(3) . . . no C8 C9 C10 125.3(3) . . . no C4 C9 C8 113.8(3) . . . no C4 C9 C10 120.8(3) . . . no C9 C10 C13 125.2(3) . . . no C11 C10 C13 112.3(3) . . . no C9 C10 C11 122.5(3) . . . no C10 C11 C12 113.5(3) . . . no O3 C12 C11 110.4(3) . . . yes O3 C12 C3 106.8(3) . . . yes C3 C12 C11 110.4(3) . . . no O3 C14 C15 111.4(3) . . . yes O4 C14 C15 126.0(4) . . . yes O3 C14 O4 122.6(3) . . . yes C3 C2 H2A 108.00 . . . no C1 C2 H2A 108.00 . . . no C1 C2 H2B 109.00 . . . no H2A C2 H2B 108.00 . . . no C3 C2 H2B 108.00 . . . no C4 C3 H3 108.00 . . . no C12 C3 H3 108.00 . . . no C2 C3 H3 108.00 . . . no C9 C4 H4 108.00 . . . no C3 C4 H4 108.00 . . . no C5 C4 H4 108.00 . . . no C6 C5 H5 107.00 . . . no O1 C5 H5 107.00 . . . no C4 C5 H5 108.00 . . . no C5 C6 H6A 110.00 . . . no C7 C6 H6B 110.00 . . . no C5 C6 H6B 110.00 . . . no C7 C6 H6A 110.00 . . . no H6A C6 H6B 108.00 . . . no C8 C7 H7A 110.00 . . . no C8 C7 H7B 110.00 . . . no H7A C7 H7B 108.00 . . . no C6 C7 H7B 110.00 . . . no C6 C7 H7A 110.00 . . . no C9 C8 H8A 109.00 . . . no C7 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no H8A C8 H8B 108.00 . . . no C9 C8 H8B 109.00 . . . no C10 C11 H11B 109.00 . . . no C10 C11 H11A 109.00 . . . no H11A C11 H11B 108.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no C11 C12 H12 110.00 . . . no C3 C12 H12 110.00 . . . no O3 C12 H12 110.00 . . . no C10 C13 H13B 110.00 . . . no C10 C13 H13A 109.00 . . . no H13A C13 H13C 109.00 . . . no C10 C13 H13C 109.00 . . . no H13A C13 H13B 110.00 . . . no H13B C13 H13C 109.00 . . . no C14 C15 H15B 109.00 . . . no C14 C15 H15C 110.00 . . . no H15A C15 H15C 109.00 . . . no H15B C15 H15C 109.00 . . . no H15A C15 H15B 110.00 . . . no C14 C15 H15A 109.00 . . . no O5 C16 O6 117.9(4) . . . yes O5 C16 C17 119.3(4) . . . yes O6 C16 C17 122.7(4) . . . yes C16 C17 C18 115.6(3) . . . no C17 C18 C19 108.2(3) . . . no C17 C18 C27 114.9(3) . . . no C19 C18 C27 109.0(3) . . . no C18 C19 C20 107.3(3) . . . no C18 C19 C24 114.0(3) . . . no C20 C19 C24 111.2(3) . . . no O5 C20 C19 112.1(3) . . . yes O5 C20 C21 108.0(3) . . . yes C19 C20 C21 113.9(3) . . . no C20 C21 C22 108.2(3) . . . no C21 C22 C23 110.0(3) . . . no C22 C23 C24 113.9(3) . . . no C19 C24 C23 113.7(3) . . . no C19 C24 C25 120.4(3) . . . no C23 C24 C25 125.7(3) . . . no C24 C25 C26 123.1(3) . . . no C24 C25 C28 124.3(3) . . . no C26 C25 C28 112.7(3) . . . no C25 C26 C27 113.7(3) . . . no O7 C27 C18 106.9(3) . . . yes O7 C27 C26 110.2(3) . . . yes C18 C27 C26 110.2(3) . . . no O7 C29 O8 122.6(3) . . . yes O7 C29 C30 112.4(4) . . . yes O8 C29 C30 125.0(4) . . . yes C16 C17 H17A 108.00 . . . no C16 C17 H17B 108.00 . . . no C18 C17 H17A 108.00 . . . no C18 C17 H17B 108.00 . . . no H17A C17 H17B 107.00 . . . no C17 C18 H18 108.00 . . . no C19 C18 H18 108.00 . . . no C27 C18 H18 108.00 . . . no C18 C19 H19 108.00 . . . no C20 C19 H19 108.00 . . . no C24 C19 H19 108.00 . . . no O5 C20 H20 108.00 . . . no C19 C20 H20 108.00 . . . no C21 C20 H20 108.00 . . . no C20 C21 H21A 110.00 . . . no C20 C21 H21B 110.00 . . . no C22 C21 H21A 110.00 . . . no C22 C21 H21B 110.00 . . . no H21A C21 H21B 108.00 . . . no C21 C22 H22A 110.00 . . . no C21 C22 H22B 110.00 . . . no C23 C22 H22A 110.00 . . . no C23 C22 H22B 110.00 . . . no H22A C22 H22B 108.00 . . . no C22 C23 H23A 109.00 . . . no C22 C23 H23B 109.00 . . . no C24 C23 H23A 109.00 . . . no C24 C23 H23B 109.00 . . . no H23A C23 H23B 108.00 . . . no C25 C26 H26A 109.00 . . . no C25 C26 H26B 109.00 . . . no C27 C26 H26A 109.00 . . . no C27 C26 H26B 109.00 . . . no H26A C26 H26B 108.00 . . . no O7 C27 H27 110.00 . . . no C18 C27 H27 110.00 . . . no C26 C27 H27 110.00 . . . no C25 C28 H28A 109.00 . . . no C25 C28 H28B 110.00 . . . no C25 C28 H28C 110.00 . . . no H28A C28 H28B 109.00 . . . no H28A C28 H28C 109.00 . . . no H28B C28 H28C 110.00 . . . no C29 C30 H30A 110.00 . . . no C29 C30 H30B 109.00 . . . no C29 C30 H30C 109.00 . . . no H30A C30 H30B 109.00 . . . no H30A C30 H30C 109.00 . . . no H30B C30 H30C 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 C5 O1 C1 O2 -166.9(4) . . . . no C5 O1 C1 C2 16.7(6) . . . . no C1 O1 C5 C6 -161.3(4) . . . . no C1 O1 C5 C4 -35.0(5) . . . . no C12 O3 C14 C15 178.3(3) . . . . no C12 O3 C14 O4 -1.9(6) . . . . no C14 O3 C12 C11 86.6(4) . . . . no C14 O3 C12 C3 -153.4(3) . . . . no C20 O5 C16 O6 -167.0(4) . . . . no C20 O5 C16 C17 17.6(5) . . . . no C16 O5 C20 C19 -36.5(5) . . . . no C16 O5 C20 C21 -162.7(3) . . . . no C27 O7 C29 O8 -2.8(6) . . . . no C27 O7 C29 C30 178.9(3) . . . . no C29 O7 C27 C18 -149.7(3) . . . . no C29 O7 C27 C26 90.6(4) . . . . no O1 C1 C2 C3 -22.7(5) . . . . no O2 C1 C2 C3 161.2(4) . . . . no C1 C2 C3 C12 168.1(3) . . . . no C1 C2 C3 C4 46.6(4) . . . . no C4 C3 C12 O3 177.5(3) . . . . no C12 C3 C4 C5 171.2(3) . . . . no C12 C3 C4 C9 47.8(4) . . . . no C2 C3 C4 C5 -63.7(3) . . . . no C4 C3 C12 C11 -62.5(4) . . . . no C2 C3 C4 C9 172.9(3) . . . . no C2 C3 C12 O3 56.4(4) . . . . no C2 C3 C12 C11 176.5(3) . . . . no C9 C4 C5 O1 -176.5(3) . . . . no C3 C4 C9 C10 -16.5(5) . . . . no C3 C4 C5 O1 58.0(4) . . . . no C3 C4 C5 C6 -178.4(3) . . . . no C3 C4 C9 C8 168.0(3) . . . . no C5 C4 C9 C8 46.7(4) . . . . no C5 C4 C9 C10 -137.9(3) . . . . no C9 C4 C5 C6 -52.9(4) . . . . no O1 C5 C6 C7 -175.9(3) . . . . no C4 C5 C6 C7 59.2(4) . . . . no C5 C6 C7 C8 -58.3(4) . . . . no C6 C7 C8 C9 54.5(4) . . . . no C7 C8 C9 C10 136.0(4) . . . . no C7 C8 C9 C4 -48.8(4) . . . . no C4 C9 C10 C13 -179.3(3) . . . . no C8 C9 C10 C11 173.6(3) . . . . no C8 C9 C10 C13 -4.4(6) . . . . no C4 C9 C10 C11 -1.3(5) . . . . no C13 C10 C11 C12 164.7(3) . . . . no C9 C10 C11 C12 -13.6(5) . . . . no C10 C11 C12 C3 45.6(4) . . . . no C10 C11 C12 O3 163.5(3) . . . . no O6 C16 C17 C18 162.2(4) . . . . no O5 C16 C17 C18 -22.6(5) . . . . no C16 C17 C18 C27 167.3(3) . . . . no C16 C17 C18 C19 45.2(4) . . . . no C17 C18 C27 C26 176.2(3) . . . . no C17 C18 C19 C20 -62.5(3) . . . . no C27 C18 C19 C20 171.9(3) . . . . no C19 C18 C27 O7 178.1(3) . . . . no C19 C18 C27 C26 -62.2(4) . . . . no C27 C18 C19 C24 48.3(4) . . . . no C17 C18 C27 O7 56.5(4) . . . . no C17 C18 C19 C24 173.9(3) . . . . no C18 C19 C20 O5 58.4(4) . . . . no C20 C19 C24 C23 45.9(4) . . . . no C18 C19 C20 C21 -178.6(3) . . . . no C24 C19 C20 O5 -176.3(3) . . . . no C20 C19 C24 C25 -138.5(3) . . . . no C18 C19 C24 C23 167.3(3) . . . . no C18 C19 C24 C25 -17.1(5) . . . . no C24 C19 C20 C21 -53.4(4) . . . . no C19 C20 C21 C22 59.9(4) . . . . no O5 C20 C21 C22 -175.0(3) . . . . no C20 C21 C22 C23 -58.4(4) . . . . no C21 C22 C23 C24 54.2(4) . . . . no C22 C23 C24 C25 136.7(4) . . . . no C22 C23 C24 C19 -48.0(4) . . . . no C19 C24 C25 C26 -1.0(5) . . . . no C19 C24 C25 C28 179.3(3) . . . . no C23 C24 C25 C26 174.0(3) . . . . no C23 C24 C25 C28 -5.7(6) . . . . no C28 C25 C26 C27 166.5(3) . . . . no C24 C25 C26 C27 -13.2(5) . . . . no C25 C26 C27 O7 162.6(3) . . . . no C25 C26 C27 C18 44.9(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 O2 C30 3.307(5) . 2_244 no O4 C11 3.269(4) . . no O6 C15 3.272(5) . 2_244 no O8 C26 3.324(4) . . no O1 H11A 2.7600 . 2_345 no O2 H30B 2.6600 . 2_244 no O2 H12 2.7800 . 1_455 no O3 H2A 2.6400 . . no O4 H2A 2.7400 . 1_655 no O4 H11B 2.8600 . . no O4 H23A 2.8200 . 1_655 no O4 H28A 2.8800 . 1_655 no O4 H12 2.4300 . . no O5 H26B 2.9200 . 2_144 no O6 H19 2.8000 . 1_455 no O6 H15B 2.5700 . 2_244 no O6 H26B 2.8200 . 2_144 no O6 H27 2.8100 . 1_455 no O7 H17A 2.6400 . . no O8 H27 2.4000 . . no O8 H8A 2.7800 . 1_454 no O8 H13A 2.8800 . 1_454 no O8 H17A 2.8400 . 1_655 no C11 O4 3.269(4) . . no C15 O6 3.272(5) . 2_254 no C26 O8 3.324(4) . . no C30 O2 3.307(5) . 2_254 no C1 H4 2.9400 . . no C1 H12 2.8900 . 1_455 no C6 H8B 3.0900 . 1_455 no C8 H13A 3.0400 . . no C8 H13C 3.0300 . . no C9 H12 3.0700 . . no C9 H5 3.0500 . 1_655 no C10 H3 3.0000 . . no C10 H5 2.9700 . 1_655 no C13 H8A 2.6500 . . no C13 H5 2.9900 . 1_655 no C13 H30B 2.9100 . 1_656 no C13 H30A 3.0200 . 1_756 no C14 H11B 3.0700 . . no C15 H28A 2.9700 . 1_655 no C16 H19 2.9500 . . no C16 H27 2.9600 . 1_455 no C20 H23B 3.0300 . 1_455 no C23 H28A 3.0500 . . no C23 H20 3.0300 . 1_655 no C23 H28C 3.0000 . . no C24 H20 3.0700 . 1_655 no C24 H27 3.0900 . . no C25 H20 3.0300 . 1_655 no C25 H18 2.9800 . . no C28 H15B 3.0200 . 1_455 no C28 H23A 2.6400 . . no C28 H15A 2.8900 . . no C28 H20 3.0200 . 1_655 no C30 H13A 2.9200 . 1_454 no H2A O3 2.6400 . . no H2A O4 2.7400 . 1_455 no H2B H4 2.5000 . . no H2B H12 2.5300 . . no H3 C10 3.0000 . . no H3 H11A 2.5800 . . no H3 H5 2.3300 . . no H4 H2B 2.5000 . . no H4 H12 2.5400 . . no H4 C1 2.9400 . . no H5 H7B 2.4400 . . no H5 H13C 2.2800 . 1_455 no H5 C13 2.9900 . 1_455 no H5 C9 3.0500 . 1_455 no H5 C10 2.9700 . 1_455 no H5 H3 2.3300 . . no H6A H8B 2.5900 . . no H6A H11B 2.3800 . 2_445 no H6B H8B 2.3900 . 1_455 no H6B H15C 2.3400 . 2_345 no H7B H5 2.4400 . . no H8A H13A 2.4400 . . no H8A C13 2.6500 . . no H8A H13C 2.5300 . . no H8A O8 2.7800 . 1_656 no H8B H6A 2.5900 . . no H8B C6 3.0900 . 1_655 no H8B H6B 2.3900 . 1_655 no H11A H3 2.5800 . . no H11A H13B 2.5900 . . no H11A O1 2.7600 . 2_355 no H11B C14 3.0700 . . no H11B H13B 2.2800 . . no H11B O4 2.8600 . . no H11B H6A 2.3800 . 2_455 no H12 H4 2.5400 . . no H12 O4 2.4300 . . no H12 O2 2.7800 . 1_655 no H12 H2B 2.5300 . . no H12 C1 2.8900 . 1_655 no H12 C9 3.0700 . . no H13A O8 2.8800 . 1_656 no H13A C30 2.9200 . 1_656 no H13A H8A 2.4400 . . no H13A C8 3.0400 . . no H13A H30B 2.0500 . 1_656 no H13B H11B 2.2800 . . no H13B H11A 2.5900 . . no H13C C8 3.0300 . . no H13C H8A 2.5300 . . no H13C H30A 2.4300 . 1_756 no H13C H5 2.2800 . 1_655 no H15A H28C 2.3100 . . no H15A C28 2.8900 . . no H15B H28A 2.1500 . 1_655 no H15B O6 2.5700 . 2_254 no H15B C28 3.0200 . 1_655 no H15C H6B 2.3400 . 2_355 no H17A O7 2.6400 . . no H17A O8 2.8400 . 1_455 no H17B H19 2.5300 . . no H17B H27 2.5200 . . no H18 C25 2.9800 . . no H18 H20 2.3300 . . no H18 H26B 2.5700 . . no H19 O6 2.8000 . 1_655 no H19 C16 2.9500 . . no H19 H17B 2.5300 . . no H19 H21A 2.6000 . . no H19 H27 2.5500 . . no H20 C23 3.0300 . 1_455 no H20 C24 3.0700 . 1_455 no H20 C25 3.0300 . 1_455 no H20 C28 3.0200 . 1_455 no H20 H18 2.3300 . . no H20 H22A 2.4300 . . no H20 H23B 2.5700 . 1_455 no H20 H28C 2.2900 . 1_455 no H21A H19 2.6000 . . no H21A H23B 2.5800 . . no H21A H26A 2.5400 . 2_244 no H21B H23B 2.4600 . 1_455 no H21B H30C 2.3300 . 2_144 no H22A H20 2.4300 . . no H23A O4 2.8200 . 1_455 no H23A C28 2.6400 . . no H23A H28A 2.4500 . . no H23A H28C 2.4900 . . no H23B C20 3.0300 . 1_655 no H23B H20 2.5700 . 1_655 no H23B H21A 2.5800 . . no H23B H21B 2.4600 . 1_655 no H26A H28B 2.2900 . . no H26A H21A 2.5400 . 2_254 no H26B H18 2.5700 . . no H26B H28B 2.5800 . . no H26B O5 2.9200 . 2_154 no H26B O6 2.8200 . 2_154 no H27 O6 2.8100 . 1_655 no H27 O8 2.4000 . . no H27 C16 2.9600 . 1_655 no H27 C24 3.0900 . . no H27 H17B 2.5200 . . no H27 H19 2.5500 . . no H28A O4 2.8800 . 1_455 no H28A C15 2.9700 . 1_455 no H28A C23 3.0500 . . no H28A H15B 2.1500 . 1_455 no H28A H23A 2.4500 . . no H28B H26A 2.2900 . . no H28B H26B 2.5800 . . no H28C C23 3.0000 . . no H28C H15A 2.3100 . . no H28C H20 2.2900 . 1_655 no H28C H23A 2.4900 . . no H30A C13 3.0200 . 1_354 no H30A H13C 2.4300 . 1_354 no H30B C13 2.9100 . 1_454 no H30B H13A 2.0500 . 1_454 no H30B O2 2.6600 . 2_254 no H30C H21B 2.3300 . 2_154 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 C15 H15B O6 0.9600 2.5700 3.272(5) 130.00 2_254 yes #===END # Attachment '- 10.cif' # CIF-file generated for Schanderl Scm152 #============================================================================== data_i072 _database_code_depnum_ccdc_archive 'CCDC 798358' #TrackingRef '- 10.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 O3' # 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 'C14 H18 O3' _chemical_formula_iupac ? _chemical_formula_weight 234.28 _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' 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 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 6.2097(7) _cell_length_b 13.1829(14) _cell_length_c 15.2549(18) _cell_angle_alpha 90 _cell_angle_beta 90.202(14) _cell_angle_gamma 90 _cell_volume 1248.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297 _cell_measurement_reflns_used 3469 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 25.91 _cell_special_details ; Cell parameters were determined by indexing 3469 reflections with I/sigma limit 6.0. ; _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.080 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.086 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type none # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.993 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; Data were collected applying an imaging plate system (STOE) with the following measurement parameters: Detector distance [mm] 70 Phi movement mode Oscillation Phi incr. [degrees] 1.2 Number of exposures 168 Irradiation / exposure [min] 6.00 For a detailed description of the method see: Sheldrick, G.M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89-98. ; _diffrn_ambient_temperature 297(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 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 9892 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0980 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.91 _diffrn_reflns_theta_full 25.91 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 4794 # number of observed reflections (> n sig(I)) _reflns_number_gt 2066 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'STOE (1998)' _computing_cell_refinement 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^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 ref _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.6(16) # 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 unk _refine_ls_number_reflns 4794 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 0.781 _refine_ls_restrained_S_all 0.781 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.140 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.027 #=============================================================================== # 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 0.0739(5) 0.14906(18) 0.4391(2) 1.000 0.0903(10) . . O2 O Uani -0.1947(5) 0.1845(2) 0.5252(3) 1.000 0.1232(14) . . O3 O Uani 0.3373(5) 0.4984(2) 0.5489(2) 1.000 0.0881(11) . . C1 C Uani -0.0233(7) 0.2115(3) 0.4953(4) 1.000 0.0829(19) . . C2 C Uani 0.0757(6) 0.3120(3) 0.5174(2) 1.000 0.0603(14) . . C3 C Uani -0.0310(6) 0.3666(3) 0.5730(3) 1.000 0.0839(17) . . C4 C Uani 0.2811(5) 0.3396(2) 0.4729(2) 1.000 0.0533(12) . . C5 C Uani 0.2816(5) 0.2907(2) 0.3822(2) 1.000 0.0570(12) . . C6 C Uani 0.2725(6) 0.1758(2) 0.3958(2) 1.000 0.0676(14) . . C7 C Uani 0.2803(7) 0.1164(3) 0.3118(3) 1.000 0.0913(19) . . C8 C Uani 0.4783(8) 0.1446(3) 0.2608(3) 1.000 0.0986(19) . . C9 C Uani 0.4829(7) 0.2571(3) 0.2420(3) 1.000 0.0879(17) . . C10 C Uani 0.4653(6) 0.3214(3) 0.3231(2) 1.000 0.0633(12) . . C11 C Uani 0.5824(6) 0.4025(3) 0.3406(3) 1.000 0.0670(16) . . C12 C Uani 0.7631(6) 0.4412(4) 0.2835(3) 1.000 0.096(2) . . C13 C Uani 0.5413(5) 0.4690(3) 0.4177(3) 1.000 0.0744(16) . . C14 C Uani 0.3280(5) 0.4514(3) 0.4644(2) 1.000 0.0634(12) . . O4 O Uani 0.0388(4) 0.34294(19) -0.0738(2) 1.000 0.0856(11) . . O5 O Uani -0.1375(6) 0.3413(3) 0.0481(2) 1.000 0.1338(17) . . O6 O Uani 0.3429(5) 0.0064(2) 0.05898(19) 1.000 0.0884(11) . . C15 C Uani -0.0120(7) 0.2961(3) 0.0016(3) 1.000 0.0863(19) . . C16 C Uani 0.0825(5) 0.1954(3) 0.0224(3) 1.000 0.0650(14) . . C17 C Uani -0.0004(7) 0.1521(4) 0.0915(3) 1.000 0.1086(19) . . C18 C Uani 0.2499(5) 0.1501(3) -0.0380(2) 1.000 0.0580(12) . . C19 C Uani 0.3557(5) 0.2355(3) -0.0901(2) 1.000 0.0560(12) . . C20 C Uani 0.1816(6) 0.2928(3) -0.1373(2) 1.000 0.0690(16) . . C21 C Uani 0.2587(6) 0.3746(3) -0.1980(3) 1.000 0.0844(17) . . C22 C Uani 0.4085(7) 0.3263(4) -0.2656(3) 1.000 0.0967(19) . . C23 C Uani 0.5966(7) 0.2765(3) -0.2193(3) 1.000 0.0883(17) . . C24 C Uani 0.5273(5) 0.1967(3) -0.1527(2) 1.000 0.0613(14) . . C25 C Uani 0.6152(5) 0.1061(3) -0.1435(2) 1.000 0.0637(16) . . C26 C Uani 0.7770(6) 0.0617(3) -0.2065(3) 1.000 0.0870(16) . . C27 C Uani 0.5570(6) 0.0369(3) -0.0693(3) 1.000 0.0730(16) . . C28 C Uani 0.4197(5) 0.0824(3) 0.0016(2) 1.000 0.0663(12) . . H3A H Uiso 0.01960 0.43040 0.58890 1.000 0.1010 calc R H3B H Uiso -0.15820 0.34200 0.59690 1.000 0.1010 calc R H3O H Uiso 0.326(7) 0.554(3) 0.535(3) 1.000 0.1060 . . H4 H Uiso 0.39910 0.30920 0.50670 1.000 0.0640 calc R H5 H Uiso 0.14760 0.31070 0.35280 1.000 0.0680 calc R H6 H Uiso 0.39390 0.15530 0.43300 1.000 0.0810 calc R H7A H Uiso 0.15270 0.13060 0.27700 1.000 0.1100 calc R H7B H Uiso 0.28240 0.04440 0.32480 1.000 0.1100 calc R H8A H Uiso 0.48000 0.10730 0.20590 1.000 0.1180 calc R H8B H Uiso 0.60560 0.12580 0.29400 1.000 0.1180 calc R H9A H Uiso 0.61630 0.27350 0.21230 1.000 0.1050 calc R H9B H Uiso 0.36500 0.27370 0.20270 1.000 0.1050 calc R H12A H Uiso 0.70860 0.45540 0.22580 1.000 0.1150 calc R H12B H Uiso 0.87410 0.39070 0.27990 1.000 0.1150 calc R H12C H Uiso 0.82130 0.50220 0.30860 1.000 0.1150 calc R H13A H Uiso 0.54650 0.53910 0.39850 1.000 0.0890 calc R H13B H Uiso 0.65720 0.45930 0.45970 1.000 0.0890 calc R H14 H Uiso 0.21250 0.48320 0.43010 1.000 0.0760 calc R H6O H Uiso 0.246(6) -0.040(3) 0.028(3) 1.000 0.1060 . . H17A H Uiso -0.10870 0.18450 0.12270 1.000 0.1310 calc R H17B H Uiso 0.04900 0.08880 0.10950 1.000 0.1310 calc R H18 H Uiso 0.17110 0.10850 -0.08060 1.000 0.0700 calc R H19 H Uiso 0.42480 0.28180 -0.04840 1.000 0.0670 calc R H20 H Uiso 0.09590 0.24430 -0.17140 1.000 0.0830 calc R H21A H Uiso 0.33520 0.42630 -0.16520 1.000 0.1010 calc R H21B H Uiso 0.13700 0.40610 -0.22730 1.000 0.1010 calc R H22A H Uiso 0.33010 0.27610 -0.29960 1.000 0.1160 calc R H22B H Uiso 0.46100 0.37800 -0.30560 1.000 0.1160 calc R H23A H Uiso 0.68040 0.32820 -0.18960 1.000 0.1060 calc R H23B H Uiso 0.68860 0.24480 -0.26270 1.000 0.1060 calc R H26A H Uiso 0.90290 0.10400 -0.20790 1.000 0.1040 calc R H26B H Uiso 0.71460 0.05830 -0.26410 1.000 0.1040 calc R H26C H Uiso 0.81640 -0.00520 -0.18760 1.000 0.1040 calc R H27A H Uiso 0.68910 0.01230 -0.04270 1.000 0.0880 calc R H27B H Uiso 0.48170 -0.02130 -0.09330 1.000 0.0880 calc R H28 H Uiso 0.51430 0.12630 0.03640 1.000 0.0800 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 0.1002(19) 0.0530(15) 0.118(2) -0.0065(16) 0.0344(18) -0.0059(15) O2 0.113(2) 0.0740(19) 0.183(3) -0.007(2) 0.064(2) -0.0237(17) O3 0.114(2) 0.0662(18) 0.084(2) -0.0189(18) -0.0072(17) -0.0105(18) C1 0.082(3) 0.051(3) 0.116(4) 0.011(3) 0.039(3) 0.001(2) C2 0.069(2) 0.054(3) 0.058(2) 0.0058(19) 0.0066(19) 0.0081(19) C3 0.082(3) 0.081(3) 0.089(3) -0.012(2) 0.024(2) 0.001(2) C4 0.055(2) 0.044(2) 0.061(2) 0.0013(17) -0.0045(17) 0.0076(17) C5 0.060(2) 0.053(2) 0.058(2) 0.0088(19) -0.0024(17) 0.0075(17) C6 0.079(2) 0.049(2) 0.075(3) 0.0011(19) 0.020(2) 0.0061(18) C7 0.128(4) 0.057(3) 0.089(3) -0.010(2) 0.017(3) 0.001(3) C8 0.148(4) 0.075(3) 0.073(3) -0.011(2) 0.033(3) 0.012(3) C9 0.118(3) 0.082(3) 0.064(3) 0.011(2) 0.024(2) 0.007(3) C10 0.081(2) 0.052(2) 0.057(2) 0.0096(19) 0.0084(19) 0.000(2) C11 0.062(2) 0.073(3) 0.066(3) 0.008(2) 0.0037(19) 0.007(2) C12 0.073(3) 0.115(4) 0.101(4) 0.033(3) 0.009(2) -0.011(3) C13 0.063(2) 0.077(3) 0.083(3) 0.019(3) -0.009(2) -0.011(2) C14 0.073(2) 0.060(2) 0.057(2) -0.0087(19) -0.0124(18) 0.0007(17) O4 0.0810(18) 0.0718(18) 0.104(2) 0.0059(17) 0.0181(17) 0.0207(15) O5 0.149(3) 0.119(3) 0.134(3) 0.002(2) 0.068(3) 0.053(2) O6 0.106(2) 0.0772(18) 0.082(2) 0.0224(17) -0.0029(16) -0.0071(16) C15 0.081(3) 0.091(4) 0.087(3) 0.002(3) 0.013(3) 0.010(3) C16 0.060(2) 0.076(3) 0.059(2) 0.005(2) 0.005(2) 0.000(2) C17 0.095(3) 0.139(4) 0.092(3) 0.020(3) 0.012(3) 0.011(3) C18 0.060(2) 0.061(2) 0.053(2) -0.0047(18) -0.0064(18) -0.0008(18) C19 0.058(2) 0.053(2) 0.057(2) 0.0008(18) -0.0035(17) -0.0006(17) C20 0.063(2) 0.072(3) 0.072(3) 0.004(2) -0.001(2) -0.0002(19) C21 0.084(3) 0.076(3) 0.093(3) 0.024(2) -0.008(3) 0.002(2) C22 0.101(3) 0.112(4) 0.077(3) 0.036(3) 0.009(3) 0.005(3) C23 0.084(3) 0.105(3) 0.076(3) 0.017(3) 0.010(2) -0.001(2) C24 0.055(2) 0.069(3) 0.060(2) -0.003(2) -0.0013(17) -0.0060(19) C25 0.051(2) 0.071(3) 0.069(3) -0.023(2) -0.0013(19) -0.002(2) C26 0.064(2) 0.093(3) 0.104(3) -0.027(3) -0.001(2) 0.000(2) C27 0.067(2) 0.062(3) 0.090(3) -0.014(2) -0.008(2) 0.0119(19) C28 0.065(2) 0.066(2) 0.068(2) 0.007(2) -0.0028(19) -0.0041(19) _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 1.334(6) . . yes O1 C6 1.445(5) . . yes O2 C1 1.213(6) . . yes O3 C14 1.431(4) . . yes O3 H3O 0.77(4) . . no O4 C15 1.344(5) . . yes O4 C20 1.472(4) . . yes O5 C15 1.212(6) . . yes O6 C28 1.414(5) . . yes O6 H6O 0.98(4) . . no C1 C2 1.499(6) . . no C2 C3 1.296(5) . . no C2 C4 1.492(5) . . no C4 C14 1.508(5) . . no C4 C5 1.526(4) . . no C5 C10 1.512(5) . . no C5 C6 1.530(4) . . no C6 C7 1.503(5) . . no C7 C8 1.504(7) . . no C8 C9 1.511(6) . . no C9 C10 1.504(6) . . no C10 C11 1.320(5) . . no C11 C13 1.490(6) . . no C11 C12 1.512(6) . . no C13 C14 1.524(5) . . no C3 H3B 0.9300 . . no C3 H3A 0.9300 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C6 H6 0.9800 . . no C7 H7A 0.9700 . . no C7 H7B 0.9700 . . no C8 H8B 0.9700 . . no C8 H8A 0.9700 . . no C9 H9A 0.9700 . . no C9 H9B 0.9700 . . no C12 H12A 0.9600 . . no C12 H12B 0.9600 . . no C12 H12C 0.9600 . . no C13 H13B 0.9700 . . no C13 H13A 0.9700 . . no C14 H14 0.9800 . . no C15 C16 1.485(6) . . no C16 C18 1.514(5) . . no C16 C17 1.306(6) . . no C18 C19 1.528(5) . . no C18 C28 1.506(5) . . no C19 C24 1.522(5) . . no C19 C20 1.501(5) . . no C20 C21 1.501(6) . . no C21 C22 1.530(6) . . no C22 C23 1.513(6) . . no C23 C24 1.526(6) . . no C24 C25 1.321(5) . . no C25 C27 1.499(6) . . no C25 C26 1.511(5) . . no C27 C28 1.504(5) . . no C17 H17A 0.9300 . . no C17 H17B 0.9300 . . no C18 H18 0.9800 . . no C19 H19 0.9800 . . no C20 H20 0.9800 . . no C21 H21A 0.9700 . . no C21 H21B 0.9700 . . no C22 H22A 0.9700 . . no C22 H22B 0.9700 . . no C23 H23A 0.9700 . . no C23 H23B 0.9700 . . no C26 H26A 0.9600 . . no C26 H26B 0.9600 . . no C26 H26C 0.9600 . . no C27 H27A 0.9700 . . no C27 H27B 0.9700 . . no C28 H28 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C6 122.1(3) . . . yes C14 O3 H3O 99(3) . . . no C15 O4 C20 120.0(3) . . . yes C28 O6 H6O 111(3) . . . no O1 C1 C2 120.3(4) . . . yes O1 C1 O2 117.4(4) . . . yes O2 C1 C2 122.3(4) . . . yes C1 C2 C3 115.3(4) . . . no C1 C2 C4 117.6(3) . . . no C3 C2 C4 127.0(4) . . . no C5 C4 C14 109.5(2) . . . no C2 C4 C14 116.3(3) . . . no C2 C4 C5 108.3(3) . . . no C4 C5 C10 115.6(3) . . . no C6 C5 C10 112.0(3) . . . no C4 C5 C6 107.2(2) . . . no O1 C6 C5 109.6(3) . . . yes C5 C6 C7 113.5(3) . . . no O1 C6 C7 107.0(3) . . . yes C6 C7 C8 110.0(3) . . . no C7 C8 C9 110.9(4) . . . no C8 C9 C10 113.3(4) . . . no C9 C10 C11 125.6(4) . . . no C5 C10 C11 120.8(3) . . . no C5 C10 C9 113.4(3) . . . no C12 C11 C13 112.7(3) . . . no C10 C11 C13 122.7(4) . . . no C10 C11 C12 124.5(4) . . . no C11 C13 C14 115.5(3) . . . no C4 C14 C13 110.9(3) . . . no O3 C14 C13 108.8(3) . . . yes O3 C14 C4 110.7(3) . . . yes C2 C3 H3B 120.00 . . . no H3A C3 H3B 120.00 . . . no C2 C3 H3A 120.00 . . . no C14 C4 H4 107.00 . . . no C5 C4 H4 107.00 . . . no C2 C4 H4 107.00 . . . no C4 C5 H5 107.00 . . . no C10 C5 H5 107.00 . . . no C6 C5 H5 107.00 . . . no C7 C6 H6 109.00 . . . no C5 C6 H6 109.00 . . . no O1 C6 H6 109.00 . . . no C6 C7 H7B 110.00 . . . no C8 C7 H7B 110.00 . . . no H7A C7 H7B 108.00 . . . no C8 C7 H7A 110.00 . . . no C6 C7 H7A 110.00 . . . no C7 C8 H8B 109.00 . . . no C9 C8 H8B 110.00 . . . no H8A C8 H8B 108.00 . . . no C9 C8 H8A 109.00 . . . no C7 C8 H8A 109.00 . . . no C8 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no C8 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C10 C9 H9A 109.00 . . . no C11 C12 H12B 109.00 . . . no H12A C12 H12B 109.00 . . . no H12A C12 H12C 109.00 . . . no C11 C12 H12C 109.00 . . . no H12B C12 H12C 110.00 . . . no C11 C12 H12A 110.00 . . . no C14 C13 H13A 108.00 . . . no C11 C13 H13A 108.00 . . . no H13A C13 H13B 107.00 . . . no C11 C13 H13B 108.00 . . . no C14 C13 H13B 108.00 . . . no C13 C14 H14 109.00 . . . no O3 C14 H14 109.00 . . . no C4 C14 H14 109.00 . . . no O4 C15 C16 120.0(4) . . . yes O5 C15 C16 124.7(4) . . . yes O4 C15 O5 115.4(4) . . . yes C15 C16 C18 119.6(4) . . . no C17 C16 C18 126.3(4) . . . no C15 C16 C17 114.0(4) . . . no C16 C18 C28 118.1(3) . . . no C19 C18 C28 110.1(3) . . . no C16 C18 C19 108.9(3) . . . no C18 C19 C20 108.1(3) . . . no C20 C19 C24 111.9(3) . . . no C18 C19 C24 112.5(3) . . . no O4 C20 C19 110.2(3) . . . yes C19 C20 C21 115.3(3) . . . no O4 C20 C21 106.1(3) . . . yes C20 C21 C22 108.2(3) . . . no C21 C22 C23 109.7(4) . . . no C22 C23 C24 113.0(3) . . . no C19 C24 C25 121.8(3) . . . no C23 C24 C25 125.2(3) . . . no C19 C24 C23 112.7(3) . . . no C24 C25 C27 122.0(3) . . . no C26 C25 C27 114.0(3) . . . no C24 C25 C26 124.0(3) . . . no C25 C27 C28 116.0(3) . . . no O6 C28 C27 110.8(3) . . . yes C18 C28 C27 110.2(3) . . . no O6 C28 C18 115.5(3) . . . yes C16 C17 H17A 120.00 . . . no C16 C17 H17B 120.00 . . . no H17A C17 H17B 120.00 . . . no C16 C18 H18 106.00 . . . no C19 C18 H18 106.00 . . . no C28 C18 H18 106.00 . . . no C18 C19 H19 108.00 . . . no C20 C19 H19 108.00 . . . no C24 C19 H19 108.00 . . . no O4 C20 H20 108.00 . . . no C19 C20 H20 108.00 . . . no C21 C20 H20 108.00 . . . no C20 C21 H21A 110.00 . . . no C20 C21 H21B 110.00 . . . no C22 C21 H21A 110.00 . . . no C22 C21 H21B 110.00 . . . no H21A C21 H21B 108.00 . . . no C21 C22 H22A 110.00 . . . no C21 C22 H22B 110.00 . . . no C23 C22 H22A 110.00 . . . no C23 C22 H22B 110.00 . . . no H22A C22 H22B 108.00 . . . no C22 C23 H23A 109.00 . . . no C22 C23 H23B 109.00 . . . no C24 C23 H23A 109.00 . . . no C24 C23 H23B 109.00 . . . no H23A C23 H23B 108.00 . . . no C25 C26 H26A 109.00 . . . no C25 C26 H26B 109.00 . . . no C25 C26 H26C 110.00 . . . no H26A C26 H26B 109.00 . . . no H26A C26 H26C 109.00 . . . no H26B C26 H26C 110.00 . . . no C25 C27 H27A 108.00 . . . no C25 C27 H27B 108.00 . . . no C28 C27 H27A 108.00 . . . no C28 C27 H27B 108.00 . . . no H27A C27 H27B 107.00 . . . no O6 C28 H28 107.00 . . . no C18 C28 H28 107.00 . . . no C27 C28 H28 107.00 . . . 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 C6 O1 C1 O2 176.6(4) . . . . no C6 O1 C1 C2 -1.7(6) . . . . no C1 O1 C6 C7 -154.3(4) . . . . no C1 O1 C6 C5 -30.8(5) . . . . no C15 O4 C20 C21 -163.0(3) . . . . no C15 O4 C20 C19 -37.6(4) . . . . no C20 O4 C15 C16 2.3(5) . . . . no C20 O4 C15 O5 -177.1(4) . . . . no O1 C1 C2 C3 -179.6(4) . . . . no O2 C1 C2 C3 2.2(7) . . . . no O1 C1 C2 C4 1.4(6) . . . . no O2 C1 C2 C4 -176.7(4) . . . . no C3 C2 C4 C5 -147.8(4) . . . . no C3 C2 C4 C14 -24.0(5) . . . . no C1 C2 C4 C14 154.8(3) . . . . no C1 C2 C4 C5 31.0(4) . . . . no C2 C4 C14 O3 59.3(4) . . . . no C5 C4 C14 C13 -56.7(3) . . . . no C14 C4 C5 C6 170.4(3) . . . . no C2 C4 C5 C6 -61.9(3) . . . . no C14 C4 C5 C10 44.8(4) . . . . no C2 C4 C14 C13 -179.8(3) . . . . no C5 C4 C14 O3 -177.6(3) . . . . no C2 C4 C5 C10 172.6(3) . . . . no C4 C5 C6 O1 62.6(3) . . . . no C6 C5 C10 C9 45.9(4) . . . . no C4 C5 C6 C7 -177.8(3) . . . . no C10 C5 C6 O1 -169.7(3) . . . . no C6 C5 C10 C11 -139.3(4) . . . . no C10 C5 C6 C7 -50.1(4) . . . . no C4 C5 C10 C9 169.0(3) . . . . no C4 C5 C10 C11 -16.2(5) . . . . no C5 C6 C7 C8 56.0(4) . . . . no O1 C6 C7 C8 177.1(3) . . . . no C6 C7 C8 C9 -57.6(5) . . . . no C7 C8 C9 C10 55.2(5) . . . . no C8 C9 C10 C11 136.0(4) . . . . no C8 C9 C10 C5 -49.5(5) . . . . no C5 C10 C11 C12 -177.5(3) . . . . no C9 C10 C11 C13 173.4(4) . . . . no C9 C10 C11 C12 -3.4(7) . . . . no C5 C10 C11 C13 -0.7(6) . . . . no C10 C11 C13 C14 -12.5(6) . . . . no C12 C11 C13 C14 164.6(3) . . . . no C11 C13 C14 C4 41.9(4) . . . . no C11 C13 C14 O3 163.8(3) . . . . no O4 C15 C16 C18 5.1(6) . . . . no O4 C15 C16 C17 -171.5(4) . . . . no O5 C15 C16 C18 -175.6(4) . . . . no O5 C15 C16 C17 7.8(6) . . . . no C15 C16 C18 C28 149.1(4) . . . . no C15 C16 C18 C19 22.7(4) . . . . no C17 C16 C18 C19 -161.2(4) . . . . no C17 C16 C18 C28 -34.8(6) . . . . no C16 C18 C19 C20 -56.1(3) . . . . no C28 C18 C19 C24 49.0(4) . . . . no C16 C18 C28 O6 47.9(4) . . . . no C16 C18 C28 C27 174.5(3) . . . . no C19 C18 C28 O6 173.7(3) . . . . no C19 C18 C28 C27 -59.7(4) . . . . no C16 C18 C19 C24 179.9(3) . . . . no C28 C18 C19 C20 173.0(3) . . . . no C18 C19 C20 O4 64.8(4) . . . . no C24 C19 C20 C21 -50.8(4) . . . . no C18 C19 C24 C23 166.8(3) . . . . no C18 C19 C24 C25 -18.4(4) . . . . no C20 C19 C24 C23 44.9(4) . . . . no C20 C19 C24 C25 -140.3(3) . . . . no C18 C19 C20 C21 -175.1(3) . . . . no C24 C19 C20 O4 -170.8(3) . . . . no O4 C20 C21 C22 180.0(3) . . . . no C19 C20 C21 C22 57.8(4) . . . . no C20 C21 C22 C23 -59.2(4) . . . . no C21 C22 C23 C24 57.4(5) . . . . no C22 C23 C24 C19 -50.1(4) . . . . no C22 C23 C24 C25 135.4(4) . . . . no C19 C24 C25 C26 176.5(3) . . . . no C19 C24 C25 C27 -2.0(5) . . . . no C23 C24 C25 C26 -9.4(6) . . . . no C23 C24 C25 C27 172.2(3) . . . . no C24 C25 C27 C28 -9.2(5) . . . . no C26 C25 C27 C28 172.2(3) . . . . no C25 C27 C28 O6 169.3(3) . . . . no C25 C27 C28 C18 40.1(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 O2 C14 3.187(5) . 2_546 no O2 O3 2.841(4) . 2_546 no O3 C3 2.897(5) . . no O3 O2 2.841(4) . 2_556 no O4 O6 3.212(4) . 2_555 no O5 O6 3.003(5) . 2_555 no O6 O5 3.003(5) . 2_545 no O6 O4 3.212(4) . 2_545 no O6 C17 2.913(6) . . no O1 H3O 2.81(4) . 2_546 no O2 H14 2.7400 . 2_546 no O2 H3B 2.3600 . . no O2 H3O 2.11(4) . 2_546 no O3 H22B 2.8300 . 1_556 no O3 H3A 2.2500 . . no O3 H6 2.6700 . 2_656 no O4 H6O 2.45(4) . 2_555 no O4 H23A 2.8400 . 1_455 no O5 H27B 2.8900 . 2_555 no O5 H6O 2.06(4) . 2_555 no O5 H17A 2.3700 . . no O6 H8A 2.7400 . . no O6 H17B 2.2600 . . no O6 H21A 2.7800 . 2_645 no C3 O3 2.897(5) . . no C12 C26 3.476(6) . 2_755 no C14 O2 3.187(5) . 2_556 no C17 O6 2.913(6) . . no C26 C12 3.476(6) . 2_745 no C1 H3O 2.84(4) . 2_546 no C1 H5 2.7500 . . no C3 H14 3.0700 . . no C3 H13B 2.8600 . 1_455 no C9 H12A 2.9800 . . no C9 H12B 3.0500 . . no C11 H4 3.0400 . . no C11 H26B 2.9900 . 2_655 no C12 H26C 3.0800 . 2_755 no C12 H9A 2.6300 . . no C13 H26B 3.0600 . 2_655 no C14 H3A 2.7200 . . no C15 H6O 2.64(4) . 2_555 no C15 H19 2.8300 . . no C16 H20 3.0300 . . no C17 H7A 3.0000 . . no C23 H26A 2.9700 . . no C23 H26B 3.0500 . . no C24 H28 3.0300 . . no C25 H12A 3.0900 . 2_645 no C25 H18 2.9200 . . no C26 H23B 2.6200 . . no C26 H12C 3.0500 . 2_745 no C27 H12A 3.0900 . 2_645 no C28 H17B 2.8400 . . no H3A O3 2.2500 . . no H3A C14 2.7200 . . no H3B O2 2.3600 . . no H3O H6 2.2500 . 2_656 no H3O H13A 2.5000 . . no H3O O1 2.81(4) . 2_556 no H3O O2 2.11(4) . 2_556 no H3O C1 2.84(4) . 2_556 no H4 H6 2.3200 . . no H4 C11 3.0400 . . no H5 H14 2.5900 . . no H5 H12B 2.2800 . 1_455 no H5 C1 2.7500 . . no H6 H4 2.3200 . . no H6 H8B 2.5300 . . no H6 O3 2.6700 . 2_646 no H6 H3O 2.2500 . 2_646 no H6O H27B 2.3800 . . no H6O O4 2.45(4) . 2_545 no H6O H17B 2.4400 . . no H6O C15 2.64(4) . 2_545 no H6O O5 2.06(4) . 2_545 no H7A H9B 2.5700 . . no H7A C17 3.0000 . . no H8A O6 2.7400 . . no H8B H6 2.5300 . . no H9A C12 2.6300 . . no H9A H17A 2.4900 . 1_655 no H9A H12A 2.4700 . . no H9A H12B 2.4500 . . no H9B H7A 2.5700 . . no H12A C25 3.0900 . 2_655 no H12A C9 2.9800 . . no H12A H9A 2.4700 . . no H12A H27B 2.3600 . 2_655 no H12A C27 3.0900 . 2_655 no H12B H5 2.2800 . 1_655 no H12B H9A 2.4500 . . no H12B C9 3.0500 . . no H12C C26 3.0500 . 2_755 no H12C H13A 2.2500 . . no H12C H13B 2.5900 . . no H13A H12C 2.2500 . . no H13A H3O 2.5000 . . no H13B H12C 2.5900 . . no H13B C3 2.8600 . 1_655 no H14 O2 2.7400 . 2_556 no H14 C3 3.0700 . . no H14 H5 2.5900 . . no H17A O5 2.3700 . . no H17A H9A 2.4900 . 1_455 no H17B O6 2.2600 . . no H17B C28 2.8400 . . no H17B H6O 2.4400 . . no H18 C25 2.9200 . . no H18 H20 2.3100 . . no H18 H26A 2.5500 . 1_455 no H18 H27B 2.5900 . . no H19 C15 2.8300 . . no H19 H28 2.4900 . . no H20 C16 3.0300 . . no H20 H18 2.3100 . . no H20 H22A 2.4800 . . no H20 H26A 2.2700 . 1_455 no H21A H23A 2.5300 . . no H21A O6 2.7800 . 2_655 no H22A H20 2.4800 . . no H22B O3 2.8300 . 1_554 no H23A O4 2.8400 . 1_655 no H23A H21A 2.5300 . . no H23B C26 2.6200 . . no H23B H26A 2.4300 . . no H23B H26B 2.4600 . . no H26A C23 2.9700 . . no H26A H18 2.5500 . 1_655 no H26A H20 2.2700 . 1_655 no H26A H23B 2.4300 . . no H26B C23 3.0500 . . no H26B H23B 2.4600 . . no H26B C11 2.9900 . 2_645 no H26B C13 3.0600 . 2_645 no H26C H27A 2.3600 . . no H26C H27B 2.5400 . . no H26C C12 3.0800 . 2_745 no H27A H26C 2.3600 . . no H27B H6O 2.3800 . . no H27B H18 2.5900 . . no H27B H26C 2.5400 . . no H27B O5 2.8900 . 2_545 no H27B H12A 2.3600 . 2_645 no H28 C24 3.0300 . . no H28 H19 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 O3 H3O O2 0.77(4) 2.11(4) 2.841(4) 159(5) 2_556 yes O6 H6O O4 0.98(4) 2.45(4) 3.212(4) 134(4) 2_545 yes O6 H6O O5 0.98(4) 2.06(4) 3.003(5) 161(3) 2_545 yes C3 H3A O3 0.9300 2.2500 2.897(5) 126.00 . yes C3 H3B O2 0.9300 2.3600 2.706(5) 102.00 . yes C17 H17A O5 0.9300 2.3700 2.717(6) 102.00 . yes C17 H17B O6 0.9300 2.2600 2.913(6) 127.00 . yes #===END # Attachment '- 14.cif' # CIF-file generated for Schwarz MS-229 CC #============================================================================== data_i206 _database_code_depnum_ccdc_archive 'CCDC 798359' #TrackingRef '- 14.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 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 'C16 H22 O5' _chemical_formula_iupac ? _chemical_formula_weight 294.34 _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' 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 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 6.7923(7) _cell_length_b 11.6086(14) _cell_length_c 20.037(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1579.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297 _cell_measurement_reflns_used 4824 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 25.93 _cell_special_details ; Cell parameters were determined by indexing 4824 reflections with I/sigma limit 6.0. ; _exptl_crystal_description stick _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.520 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.060 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.091 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type none # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.994 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; Data were collected applying an imaging plate system (STOE) with the following measurement parameters: Detector distance [mm] 70 Phi movement mode Oscillation Phi incr. [degrees] 1.0 Number of exposures 221 Irradiation / exposure [min] 11.00 For a detailed description of the method see: Sheldrick, G.M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89-98. ; _diffrn_ambient_temperature 297(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 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 13786 _diffrn_reflns_av_R_equivalents 0.1121 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.93 _diffrn_reflns_theta_full 25.93 _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 3068 # number of observed reflections (> n sig(I)) _reflns_number_gt 1455 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'STOE (1998)' _computing_cell_refinement 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^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 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 -1.0(17) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration syn _refine_ls_number_reflns 3068 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_restrained_S_all 0.785 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.159 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.030 #=============================================================================== # 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 -0.3441(3) -0.0144(2) 0.16766(11) 1.000 0.0703(9) . . O2 O Uani -0.3816(4) -0.1777(2) 0.11574(13) 1.000 0.0808(10) . . O3 O Uani -0.2363(3) 0.3075(3) 0.31752(13) 1.000 0.0904(10) . . O4 O Uani 0.1994(3) 0.0200(2) -0.00540(11) 1.000 0.0672(9) . . O5 O Uani 0.5269(3) 0.0187(2) 0.00407(12) 1.000 0.0786(9) . . C1 C Uani -0.2833(5) -0.0901(3) 0.12105(17) 1.000 0.0612(11) . . C2 C Uani -0.1012(5) -0.0678(3) 0.08216(18) 1.000 0.0631(11) . . C3 C Uani -0.0280(4) 0.0562(3) 0.08340(16) 1.000 0.0560(11) . . C4 C Uani -0.0469(4) 0.1015(3) 0.15484(16) 1.000 0.0573(11) . . C5 C Uani -0.2613(4) 0.1006(3) 0.17335(16) 1.000 0.0579(11) . . C6 C Uani -0.2984(4) 0.1417(3) 0.24469(16) 1.000 0.0605(11) . . C7 C Uani -0.2215(4) 0.2648(3) 0.25109(16) 1.000 0.0657(14) . . C8 C Uani -0.0066(5) 0.2741(3) 0.23178(16) 1.000 0.0687(14) . . C9 C Uani 0.0447(5) 0.2190(3) 0.16536(17) 1.000 0.0593(11) . . C10 C Uani 0.1760(4) 0.2623(3) 0.12256(18) 1.000 0.0609(11) . . C11 C Uani 0.2333(5) 0.1979(3) 0.05895(17) 1.000 0.0673(12) . . C12 C Uani 0.1807(4) 0.0711(3) 0.06087(15) 1.000 0.0576(11) . . C13 C Uani -0.5145(5) 0.1298(4) 0.26436(19) 1.000 0.0823(16) . . C14 C Uani 0.2867(5) 0.3728(3) 0.1312(2) 1.000 0.0767(16) . . C15 C Uani 0.3816(5) -0.0052(3) -0.02593(17) 1.000 0.0679(11) . . C16 C Uani 0.3764(7) -0.0671(4) -0.0919(2) 1.000 0.1130(19) . . H2A H Uiso -0.12480 -0.08960 0.03610 1.000 0.0760 calc R H2B H Uiso 0.00240 -0.11720 0.09920 1.000 0.0760 calc R H3 H Uiso -0.11310 0.10250 0.05440 1.000 0.0670 calc R H3A H Uiso -0.35260 0.31170 0.32820 1.000 0.1080 calc R H4 H Uiso 0.02100 0.04710 0.18430 1.000 0.0690 calc R H5 H Uiso -0.33210 0.15170 0.14270 1.000 0.0700 calc R H6 H Uiso -0.22090 0.09290 0.27470 1.000 0.0730 calc R H7 H Uiso -0.29880 0.31470 0.22160 1.000 0.0790 calc R H8A H Uiso 0.07220 0.23820 0.26640 1.000 0.0820 calc R H8B H Uiso 0.02910 0.35490 0.23010 1.000 0.0820 calc R H11A H Uiso 0.16750 0.23350 0.02120 1.000 0.0810 calc R H11B H Uiso 0.37400 0.20560 0.05210 1.000 0.0810 calc R H12 H Uiso 0.26880 0.03120 0.09190 1.000 0.0690 calc R H13A H Uiso -0.55390 0.05070 0.26040 1.000 0.0990 calc R H13B H Uiso -0.59400 0.17650 0.23540 1.000 0.0990 calc R H13C H Uiso -0.53160 0.15480 0.30970 1.000 0.0990 calc R H14A H Uiso 0.36420 0.36910 0.17120 1.000 0.0920 calc R H14B H Uiso 0.19530 0.43560 0.13430 1.000 0.0920 calc R H14C H Uiso 0.37170 0.38450 0.09350 1.000 0.0920 calc R H16A H Uiso 0.31410 -0.01900 -0.12470 1.000 0.1360 calc R H16B H Uiso 0.30330 -0.13750 -0.08720 1.000 0.1360 calc R H16C H Uiso 0.50830 -0.08440 -0.10580 1.000 0.1360 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 0.0709(14) 0.0657(16) 0.0744(15) -0.0069(13) 0.0155(12) -0.0095(12) O2 0.0874(17) 0.0629(17) 0.0921(19) -0.0011(14) 0.0207(15) -0.0145(15) O3 0.0650(14) 0.124(2) 0.0823(18) -0.0377(17) 0.0068(14) 0.0011(16) O4 0.0601(13) 0.0862(18) 0.0554(13) -0.0099(13) 0.0062(12) -0.0101(12) O5 0.0572(13) 0.106(2) 0.0725(15) -0.0084(15) 0.0080(13) 0.0003(14) C1 0.0596(19) 0.060(2) 0.064(2) 0.006(2) 0.0028(18) -0.0033(19) C2 0.0552(19) 0.069(2) 0.065(2) 0.0028(19) 0.0007(16) -0.0039(17) C3 0.0503(17) 0.065(2) 0.0527(19) 0.0060(17) -0.0032(15) 0.0000(16) C4 0.0478(17) 0.069(2) 0.055(2) 0.0008(18) 0.0020(15) 0.0052(16) C5 0.0506(17) 0.065(2) 0.058(2) 0.0010(17) 0.0030(16) -0.0029(16) C6 0.0516(19) 0.070(2) 0.060(2) 0.0007(18) 0.0055(16) 0.0067(16) C7 0.058(2) 0.078(3) 0.061(2) -0.013(2) -0.0034(17) 0.0076(18) C8 0.058(2) 0.083(3) 0.065(2) -0.012(2) -0.0045(18) 0.0023(19) C9 0.0538(17) 0.064(2) 0.060(2) -0.0059(18) -0.0053(17) 0.0007(17) C10 0.0537(18) 0.060(2) 0.069(2) 0.0053(18) -0.0035(17) -0.0026(17) C11 0.066(2) 0.071(2) 0.065(2) 0.0041(18) 0.0028(19) -0.0073(19) C12 0.060(2) 0.066(2) 0.0468(18) -0.0007(16) -0.0012(15) 0.0004(17) C13 0.073(2) 0.096(3) 0.078(3) -0.012(2) 0.009(2) 0.004(2) C14 0.069(2) 0.074(3) 0.087(3) -0.001(2) -0.001(2) -0.009(2) C15 0.0577(19) 0.074(2) 0.072(2) -0.007(2) 0.0110(19) -0.0106(19) C16 0.113(3) 0.138(4) 0.088(3) -0.048(3) 0.029(3) -0.033(3) _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 1.347(4) . . yes O1 C5 1.453(4) . . yes O2 C1 1.221(4) . . yes O3 C7 1.424(4) . . yes O4 C12 1.460(4) . . yes O4 C15 1.337(4) . . yes O5 C15 1.188(4) . . yes O3 H3A 0.8200 . . no C1 C2 1.485(5) . . no C2 C3 1.523(5) . . no C3 C12 1.498(4) . . no C3 C4 1.530(5) . . no C4 C5 1.503(4) . . no C4 C9 1.514(5) . . no C5 C6 1.528(5) . . no C6 C7 1.527(5) . . no C6 C13 1.526(4) . . no C7 C8 1.514(4) . . no C8 C9 1.517(5) . . no C9 C10 1.336(5) . . no C10 C11 1.528(5) . . no C10 C14 1.497(5) . . no C11 C12 1.515(5) . . no C15 C16 1.505(5) . . no C2 H2A 0.9700 . . no C2 H2B 0.9700 . . no C3 H3 0.9800 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C6 H6 0.9800 . . no C7 H7 0.9800 . . no C8 H8A 0.9700 . . no C8 H8B 0.9700 . . no C11 H11A 0.9700 . . no C11 H11B 0.9700 . . no C12 H12 0.9800 . . no C13 H13A 0.9600 . . no C13 H13B 0.9600 . . no C13 H13C 0.9600 . . no C14 H14A 0.9600 . . no C14 H14B 0.9600 . . no C14 H14C 0.9600 . . no C16 H16A 0.9600 . . no C16 H16B 0.9600 . . no C16 H16C 0.9600 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 122.4(2) . . . yes C12 O4 C15 116.7(2) . . . yes C7 O3 H3A 109.00 . . . no O1 C1 O2 115.9(3) . . . yes O1 C1 C2 120.4(3) . . . yes O2 C1 C2 123.7(3) . . . yes C1 C2 C3 115.4(3) . . . no C2 C3 C12 114.4(3) . . . no C4 C3 C12 108.8(2) . . . no C2 C3 C4 108.2(3) . . . no C3 C4 C5 108.0(2) . . . no C5 C4 C9 111.7(3) . . . no C3 C4 C9 113.9(3) . . . no O1 C5 C4 111.2(3) . . . yes C4 C5 C6 112.9(2) . . . no O1 C5 C6 107.3(2) . . . yes C5 C6 C7 108.3(3) . . . no C5 C6 C13 111.8(3) . . . no C7 C6 C13 113.1(3) . . . no O3 C7 C6 112.3(3) . . . yes O3 C7 C8 106.4(2) . . . yes C6 C7 C8 112.0(3) . . . no C7 C8 C9 114.6(3) . . . no C4 C9 C10 121.6(3) . . . no C8 C9 C10 123.9(3) . . . no C4 C9 C8 114.1(3) . . . no C9 C10 C14 125.7(3) . . . no C11 C10 C14 112.8(3) . . . no C9 C10 C11 121.4(3) . . . no C10 C11 C12 113.2(3) . . . no O4 C12 C11 110.6(3) . . . yes C3 C12 C11 110.1(3) . . . no O4 C12 C3 108.0(2) . . . yes O4 C15 C16 110.7(3) . . . yes O5 C15 C16 125.1(3) . . . yes O4 C15 O5 124.2(3) . . . yes C1 C2 H2A 108.00 . . . no C1 C2 H2B 108.00 . . . no C3 C2 H2A 108.00 . . . no C3 C2 H2B 108.00 . . . no H2A C2 H2B 107.00 . . . no C2 C3 H3 108.00 . . . no C4 C3 H3 108.00 . . . no C12 C3 H3 108.00 . . . no C3 C4 H4 108.00 . . . no C5 C4 H4 108.00 . . . no C9 C4 H4 108.00 . . . no O1 C5 H5 108.00 . . . no C4 C5 H5 108.00 . . . no C6 C5 H5 108.00 . . . no C5 C6 H6 108.00 . . . no C7 C6 H6 108.00 . . . no C13 C6 H6 108.00 . . . no O3 C7 H7 109.00 . . . no C6 C7 H7 109.00 . . . no C8 C7 H7 109.00 . . . no C7 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no C9 C8 H8A 109.00 . . . no C9 C8 H8B 109.00 . . . no H8A C8 H8B 108.00 . . . no C10 C11 H11A 109.00 . . . no C10 C11 H11B 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no O4 C12 H12 109.00 . . . no C3 C12 H12 109.00 . . . no C11 C12 H12 109.00 . . . no C6 C13 H13A 109.00 . . . no C6 C13 H13B 109.00 . . . no C6 C13 H13C 109.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no C10 C14 H14A 109.00 . . . no C10 C14 H14B 109.00 . . . no C10 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no C15 C16 H16A 109.00 . . . no C15 C16 H16B 109.00 . . . no C15 C16 H16C 109.00 . . . no H16A C16 H16B 109.00 . . . no H16A C16 H16C 110.00 . . . no H16B C16 H16C 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 C5 O1 C1 O2 -170.7(3) . . . . no C5 O1 C1 C2 12.4(4) . . . . no C1 O1 C5 C6 -157.3(3) . . . . no C1 O1 C5 C4 -33.4(4) . . . . no C15 O4 C12 C3 -161.3(3) . . . . no C12 O4 C15 C16 174.7(3) . . . . no C12 O4 C15 O5 -5.5(5) . . . . no C15 O4 C12 C11 78.2(3) . . . . no O2 C1 C2 C3 166.0(3) . . . . no O1 C1 C2 C3 -17.4(5) . . . . no C1 C2 C3 C4 42.3(4) . . . . no C1 C2 C3 C12 163.7(3) . . . . no C2 C3 C12 O4 54.9(3) . . . . no C2 C3 C4 C5 -62.6(3) . . . . no C2 C3 C12 C11 175.7(3) . . . . no C4 C3 C12 O4 176.0(3) . . . . no C12 C3 C4 C9 47.8(4) . . . . no C12 C3 C4 C5 172.6(3) . . . . no C2 C3 C4 C9 172.6(3) . . . . no C4 C3 C12 C11 -63.2(3) . . . . no C3 C4 C9 C8 169.0(3) . . . . no C5 C4 C9 C10 -140.9(3) . . . . no C3 C4 C9 C10 -18.2(4) . . . . no C9 C4 C5 C6 -55.3(4) . . . . no C3 C4 C5 C6 178.7(3) . . . . no C9 C4 C5 O1 -175.9(3) . . . . no C5 C4 C9 C8 46.2(4) . . . . no C3 C4 C5 O1 58.1(3) . . . . no O1 C5 C6 C7 -177.3(2) . . . . no C4 C5 C6 C7 59.8(3) . . . . no C4 C5 C6 C13 -174.9(3) . . . . no O1 C5 C6 C13 -52.0(4) . . . . no C5 C6 C7 O3 -175.6(2) . . . . no C13 C6 C7 C8 179.6(3) . . . . no C5 C6 C7 C8 -55.9(3) . . . . no C13 C6 C7 O3 59.9(3) . . . . no C6 C7 C8 C9 49.7(4) . . . . no O3 C7 C8 C9 172.8(3) . . . . no C7 C8 C9 C10 143.0(3) . . . . no C7 C8 C9 C4 -44.3(4) . . . . no C4 C9 C10 C11 3.0(5) . . . . no C4 C9 C10 C14 -174.8(3) . . . . no C8 C9 C10 C11 175.1(3) . . . . no C8 C9 C10 C14 -2.7(5) . . . . no C14 C10 C11 C12 159.8(3) . . . . no C9 C10 C11 C12 -18.2(4) . . . . no C10 C11 C12 O4 167.9(2) . . . . no C10 C11 C12 C3 48.6(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 O3 2.925(3) . 4_445 no O2 C13 3.356(5) . 4_445 no O3 C2 3.375(4) . 4_555 no O3 O2 2.925(3) . 4_455 no O5 C11 3.084(4) . . no O5 C1 2.958(4) . 1_655 no O5 C2 3.137(4) . 1_655 no O1 H13A 2.4600 . . no O1 H3A 2.8900 . 4_445 no O2 H16B 2.5500 . 3_445 no O2 H13C 2.5200 . 4_445 no O2 H3A 2.1300 . 4_445 no O3 H13C 2.6800 . . no O3 H2B 2.4600 . 4_555 no O4 H2A 2.6800 . . no O5 H2A 2.7500 . 1_655 no O5 H3 2.8200 . 1_655 no O5 H11B 2.5900 . . no O5 H12 2.4900 . . no C1 O5 2.958(4) . 1_455 no C2 O3 3.375(4) . 4_545 no C2 O5 3.137(4) . 1_455 no C11 O5 3.084(4) . . no C13 O2 3.356(5) . 4_455 no C1 H3A 2.9100 . 4_445 no C1 H4 2.9000 . . no C8 H14A 3.0100 . . no C8 H14B 3.0300 . . no C8 H13B 3.0200 . 1_655 no C9 H13B 2.8700 . 1_655 no C9 H12 3.0400 . . no C10 H3 3.0300 . . no C10 H13B 2.9200 . 1_655 no C13 H3A 2.7000 . . no C13 H8A 3.0800 . 1_455 no C14 H8B 2.6500 . . no C15 H11B 2.9000 . . no C16 H14B 2.7800 . 3_555 no H2A O4 2.6800 . . no H2A O5 2.7500 . 1_455 no H2B H4 2.5600 . . no H2B H12 2.5000 . . no H2B O3 2.4600 . 4_545 no H3 O5 2.8200 . 1_455 no H3 C10 3.0300 . . no H3 H5 2.3800 . . no H3 H11A 2.5300 . . no H3A C13 2.7000 . . no H3A H13C 2.2200 . . no H3A O1 2.8900 . 4_455 no H3A O2 2.1300 . 4_455 no H3A C1 2.9100 . 4_455 no H4 C1 2.9000 . . no H4 H2B 2.5600 . . no H4 H6 2.5000 . . no H4 H12 2.5100 . . no H5 H3 2.3800 . . no H5 H7 2.4800 . . no H5 H13B 2.5900 . . no H6 H4 2.5000 . . no H6 H14B 2.5900 . 4_545 no H7 H5 2.4800 . . no H7 H13B 2.5800 . . no H7 H14A 2.5800 . 1_455 no H8A C13 3.0800 . 1_655 no H8A H13B 2.4600 . 1_655 no H8B C14 2.6500 . . no H8B H14A 2.5700 . . no H8B H14B 2.4200 . . no H11A H3 2.5300 . . no H11A H11B 2.5800 . 3_455 no H11B O5 2.5900 . . no H11B C15 2.9000 . . no H11B H14C 2.2400 . . no H11B H11A 2.5800 . 3_555 no H12 O5 2.4900 . . no H12 C9 3.0400 . . no H12 H2B 2.5000 . . no H12 H4 2.5100 . . no H13A O1 2.4600 . . no H13B C8 3.0200 . 1_455 no H13B C9 2.8700 . 1_455 no H13B C10 2.9200 . 1_455 no H13B H5 2.5900 . . no H13B H7 2.5800 . . no H13B H8A 2.4600 . 1_455 no H13B H14A 2.6000 . 1_455 no H13C O3 2.6800 . . no H13C H3A 2.2200 . . no H13C O2 2.5200 . 4_455 no H14A C8 3.0100 . . no H14A H7 2.5800 . 1_655 no H14A H8B 2.5700 . . no H14A H13B 2.6000 . 1_655 no H14B C8 3.0300 . . no H14B H8B 2.4200 . . no H14B C16 2.7800 . 3_455 no H14B H16C 2.2200 . 3_455 no H14B H6 2.5900 . 4_555 no H14C H11B 2.2400 . . no H16B O2 2.5500 . 3_545 no H16C H14B 2.2200 . 3_555 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 O3 H3A O2 0.8200 2.1300 2.925(3) 163.00 4_455 yes C2 H2B O3 0.9700 2.4600 3.375(4) 156.00 4_545 yes C11 H11B O5 0.9700 2.5900 3.084(4) 112.00 . yes C13 H13A O1 0.9600 2.4600 2.810(5) 101.00 . yes C13 H13C O2 0.9600 2.5200 3.356(5) 145.00 4_455 yes C16 H16B O2 0.9600 2.5500 3.475(5) 161.00 3_545 yes #===END # Attachment '- 15.cif' # CIF-file generated for Schanderl Scm 146 #============================================================================== data_i198 _database_code_depnum_ccdc_archive 'CCDC 798360' #TrackingRef '- 15.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H22 O4' _chemical_formula_iupac ? _chemical_formula_weight 278.34 _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' 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 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 6.9797(7) _cell_length_b 11.9507(9) _cell_length_c 17.3512(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1447.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 26.94 _cell_special_details ; Cell parameters were determined by indexing 8000 reflections with I/sigma limit 6.0. ; _exptl_crystal_description prism _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.160 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.091 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type none # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.986 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; Data were collected applying an imaging plate system (STOE) with the following measurement parameters: Detector distance [mm] 65 Phi movement mode Oscillation Phi incr. [degrees] 1.0 Number of exposures 202 Irradiation / exposure [min] 8.00 For a detailed description of the method see: Sheldrick, G.M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89-98. ; _diffrn_ambient_temperature 297(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 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 12883 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.94 _diffrn_reflns_theta_full 26.94 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3128 # number of observed reflections (> n sig(I)) _reflns_number_gt 2566 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'STOE (1998)' _computing_cell_refinement 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^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 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 -0.3(12) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration syn _refine_ls_number_reflns 3128 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.261 _refine_diff_density_min -0.234 _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 -0.3420(3) 0.18410(17) -0.52257(10) 1.000 0.0749(6) . . O2 O Uani -0.4481(2) 0.17971(11) -0.40186(8) 1.000 0.0476(4) . . O3 O Uani -0.91905(16) -0.10616(10) -0.41552(8) 1.000 0.0396(4) . . O4 O Uani -1.2390(2) -0.08535(15) -0.42623(12) 1.000 0.0635(6) . . C1 C Uani -0.4559(3) 0.14930(17) -0.47740(13) 1.000 0.0502(7) . . C2 C Uani -0.6248(3) 0.07219(16) -0.49003(11) 1.000 0.0436(6) . . C3 C Uani -0.6810(2) 0.03528(15) -0.40913(10) 1.000 0.0349(5) . . C4 C Uani -0.6071(3) 0.13119(14) -0.35853(11) 1.000 0.0377(5) . . C5 C Uani -0.5275(3) 0.09119(15) -0.28130(11) 1.000 0.0370(5) . . C6 C Uani -0.6411(3) 0.00223(14) -0.23751(10) 1.000 0.0353(5) . . C7 C Uani -0.8243(3) -0.02717(15) -0.25042(11) 1.000 0.0386(5) . . C8 C Uani -0.9496(3) 0.03057(17) -0.31055(11) 1.000 0.0425(6) . . C9 C Uani -0.8931(3) 0.01144(15) -0.39443(11) 1.000 0.0375(5) . . C10 C Uani -0.4784(3) 0.18733(17) -0.22551(12) 1.000 0.0491(6) . . C11 C Uani -0.3592(3) 0.1442(2) -0.15784(13) 1.000 0.0568(7) . . C12 C Uani -0.4560(3) 0.04636(18) -0.11733(12) 1.000 0.0504(7) . . C13 C Uani -0.5171(3) -0.04584(16) -0.17407(12) 1.000 0.0440(6) . . C14 C Uani -0.9281(3) -0.11850(19) -0.20625(14) 1.000 0.0545(7) . . C15 C Uani -1.0985(3) -0.14368(17) -0.42786(11) 1.000 0.0431(6) . . C16 C Uani -1.0987(3) -0.26670(19) -0.44390(15) 1.000 0.0564(7) . . H2A H Uiso -0.58860 0.00840 -0.52140 1.000 0.0520 calc R H2B H Uiso -0.72950 0.11140 -0.51500 1.000 0.0520 calc R H3 H Uiso -0.60800 -0.03230 -0.39640 1.000 0.0420 calc R H4 H Uiso -0.70800 0.18700 -0.35050 1.000 0.0450 calc R H5 H Uiso -0.40450 0.05590 -0.29360 1.000 0.0440 calc R H8A H Uiso -1.08050 0.00520 -0.30370 1.000 0.0510 calc R H8B H Uiso -0.94760 0.11040 -0.30060 1.000 0.0510 calc R H9 H Uiso -0.97180 0.05870 -0.42800 1.000 0.0450 calc R H10A H Uiso -0.40720 0.24470 -0.25280 1.000 0.0590 calc R H10B H Uiso -0.59580 0.22070 -0.20630 1.000 0.0590 calc R H11A H Uiso -0.23450 0.12080 -0.17650 1.000 0.0680 calc R H11B H Uiso -0.33980 0.20450 -0.12120 1.000 0.0680 calc R H12A H Uiso -0.56790 0.07330 -0.08990 1.000 0.0610 calc R H12B H Uiso -0.36830 0.01490 -0.07970 1.000 0.0610 calc R H13A H Uiso -0.40420 -0.08020 -0.19650 1.000 0.0530 calc R H13B H Uiso -0.58790 -0.10330 -0.14670 1.000 0.0530 calc R H14A H Uiso -0.86250 -0.18840 -0.21330 1.000 0.0650 calc R H14B H Uiso -1.05690 -0.12490 -0.22500 1.000 0.0650 calc R H14C H Uiso -0.93030 -0.10000 -0.15240 1.000 0.0650 calc R H16A H Uiso -1.02270 -0.28160 -0.48890 1.000 0.0680 calc R H16B H Uiso -1.22770 -0.29150 -0.45260 1.000 0.0680 calc R H16C H Uiso -1.04580 -0.30590 -0.40050 1.000 0.0680 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 0.0925(13) 0.0806(11) 0.0515(9) -0.0029(9) 0.0214(9) -0.0431(11) O2 0.0587(8) 0.0425(7) 0.0415(7) -0.0018(6) 0.0050(6) -0.0167(6) O3 0.0320(6) 0.0392(6) 0.0475(7) -0.0048(5) -0.0010(5) -0.0028(5) O4 0.0357(7) 0.0699(10) 0.0849(12) -0.0061(9) -0.0069(8) -0.0006(7) C1 0.0639(13) 0.0432(10) 0.0434(11) -0.0022(9) 0.0048(9) -0.0119(10) C2 0.0515(11) 0.0409(9) 0.0385(10) -0.0048(8) 0.0039(8) -0.0071(8) C3 0.0358(8) 0.0332(8) 0.0357(9) -0.0007(7) -0.0015(7) -0.0007(6) C4 0.0408(9) 0.0329(8) 0.0393(10) -0.0020(7) 0.0024(8) -0.0014(7) C5 0.0347(8) 0.0369(8) 0.0395(9) -0.0024(7) -0.0011(7) -0.0031(7) C6 0.0373(9) 0.0339(8) 0.0347(9) -0.0044(7) 0.0016(7) 0.0018(7) C7 0.0371(9) 0.0395(9) 0.0391(9) -0.0052(8) 0.0064(7) -0.0001(7) C8 0.0309(9) 0.0500(10) 0.0466(10) -0.0074(9) 0.0039(7) 0.0036(8) C9 0.0348(9) 0.0351(8) 0.0427(10) -0.0018(7) -0.0033(7) 0.0006(7) C10 0.0608(12) 0.0416(10) 0.0449(11) -0.0036(9) -0.0036(9) -0.0130(9) C11 0.0590(13) 0.0637(13) 0.0478(12) -0.0116(11) -0.0107(10) -0.0118(11) C12 0.0565(12) 0.0572(12) 0.0376(10) -0.0036(9) -0.0077(9) 0.0090(10) C13 0.0468(10) 0.0415(10) 0.0437(10) 0.0042(8) -0.0021(8) 0.0029(8) C14 0.0468(11) 0.0641(13) 0.0526(13) 0.0039(10) 0.0095(10) -0.0123(10) C15 0.0328(9) 0.0547(10) 0.0417(10) -0.0004(9) -0.0018(8) -0.0070(8) C16 0.0461(11) 0.0553(11) 0.0679(14) -0.0037(11) -0.0057(10) -0.0137(9) _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 1.191(3) . . yes O2 C1 1.361(3) . . yes O2 C4 1.461(2) . . yes O3 C9 1.464(2) . . yes O3 C15 1.348(2) . . yes O4 C15 1.204(3) . . yes C1 C2 1.512(3) . . no C2 C3 1.523(3) . . no C3 C4 1.533(3) . . no C3 C9 1.529(3) . . no C4 C5 1.527(3) . . no C5 C6 1.529(3) . . no C5 C10 1.541(3) . . no C6 C7 1.345(3) . . no C6 C13 1.514(3) . . no C7 C8 1.526(3) . . no C7 C14 1.518(3) . . no C8 C9 1.525(3) . . no C10 C11 1.529(3) . . no C11 C12 1.522(3) . . no C12 C13 1.538(3) . . no C15 C16 1.496(3) . . no C2 H2A 0.9700 . . no C2 H2B 0.9700 . . no C3 H3 0.9800 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C8 H8A 0.9700 . . no C8 H8B 0.9700 . . no C9 H9 0.9800 . . no C10 H10A 0.9700 . . no C10 H10B 0.9700 . . no C11 H11A 0.9700 . . no C11 H11B 0.9700 . . no C12 H12A 0.9700 . . no C12 H12B 0.9700 . . no C13 H13A 0.9700 . . no C13 H13B 0.9700 . . no C14 H14A 0.9600 . . no C14 H14B 0.9600 . . no C14 H14C 0.9600 . . no C16 H16A 0.9600 . . no C16 H16B 0.9600 . . no C16 H16C 0.9600 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 111.06(15) . . . yes C9 O3 C15 118.32(14) . . . yes O1 C1 O2 120.9(2) . . . yes O1 C1 C2 129.6(2) . . . yes O2 C1 C2 109.48(17) . . . yes C1 C2 C3 104.11(16) . . . no C2 C3 C4 102.98(14) . . . no C2 C3 C9 117.20(15) . . . no C4 C3 C9 111.69(15) . . . no O2 C4 C3 104.93(14) . . . yes O2 C4 C5 107.43(16) . . . yes C3 C4 C5 113.01(14) . . . no C4 C5 C6 117.72(17) . . . no C4 C5 C10 113.50(15) . . . no C6 C5 C10 108.77(15) . . . no C5 C6 C7 126.31(17) . . . no C5 C6 C13 109.20(17) . . . no C7 C6 C13 124.45(17) . . . no C6 C7 C8 122.72(17) . . . no C6 C7 C14 123.89(18) . . . no C8 C7 C14 113.38(17) . . . no C7 C8 C9 115.87(17) . . . no O3 C9 C3 104.90(14) . . . yes O3 C9 C8 110.52(15) . . . yes C3 C9 C8 112.43(16) . . . no C5 C10 C11 110.62(17) . . . no C10 C11 C12 111.84(17) . . . no C11 C12 C13 112.20(17) . . . no C6 C13 C12 110.62(16) . . . no O3 C15 O4 124.12(19) . . . yes O3 C15 C16 110.94(17) . . . yes O4 C15 C16 124.94(19) . . . yes C1 C2 H2A 111.00 . . . no C1 C2 H2B 111.00 . . . no C3 C2 H2A 111.00 . . . no C3 C2 H2B 111.00 . . . no H2A C2 H2B 109.00 . . . no C2 C3 H3 108.00 . . . no C4 C3 H3 108.00 . . . no C9 C3 H3 108.00 . . . no O2 C4 H4 110.00 . . . no C3 C4 H4 110.00 . . . no C5 C4 H4 110.00 . . . no C4 C5 H5 105.00 . . . no C6 C5 H5 105.00 . . . no C10 C5 H5 105.00 . . . no C7 C8 H8A 108.00 . . . no C7 C8 H8B 108.00 . . . no C9 C8 H8A 108.00 . . . no C9 C8 H8B 108.00 . . . no H8A C8 H8B 107.00 . . . no O3 C9 H9 110.00 . . . no C3 C9 H9 110.00 . . . no C8 C9 H9 110.00 . . . no C5 C10 H10A 110.00 . . . no C5 C10 H10B 110.00 . . . no C11 C10 H10A 110.00 . . . no C11 C10 H10B 110.00 . . . no H10A C10 H10B 108.00 . . . no C10 C11 H11A 109.00 . . . no C10 C11 H11B 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no C11 C12 H12A 109.00 . . . no C11 C12 H12B 109.00 . . . no C13 C12 H12A 109.00 . . . no C13 C12 H12B 109.00 . . . no H12A C12 H12B 108.00 . . . no C6 C13 H13A 109.00 . . . no C6 C13 H13B 109.00 . . . no C12 C13 H13A 110.00 . . . no C12 C13 H13B 110.00 . . . no H13A C13 H13B 108.00 . . . no C7 C14 H14A 109.00 . . . no C7 C14 H14B 109.00 . . . no C7 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no C15 C16 H16A 109.00 . . . no C15 C16 H16B 109.00 . . . no C15 C16 H16C 109.00 . . . no H16A C16 H16B 109.00 . . . no H16A C16 H16C 110.00 . . . no H16B C16 H16C 109.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O2 C1 O1 177.2(2) . . . . no C4 O2 C1 C2 -1.7(2) . . . . no C1 O2 C4 C5 138.63(15) . . . . no C1 O2 C4 C3 18.12(19) . . . . no C9 O3 C15 O4 3.7(3) . . . . no C15 O3 C9 C3 -162.99(15) . . . . no C15 O3 C9 C8 75.6(2) . . . . no C9 O3 C15 C16 -176.46(17) . . . . no O1 C1 C2 C3 165.7(2) . . . . no O2 C1 C2 C3 -15.5(2) . . . . no C1 C2 C3 C4 25.14(18) . . . . no C1 C2 C3 C9 148.15(16) . . . . no C9 C3 C4 C5 90.21(19) . . . . no C4 C3 C9 O3 -154.09(14) . . . . no C4 C3 C9 C8 -33.9(2) . . . . no C9 C3 C4 O2 -153.05(14) . . . . no C2 C3 C9 O3 87.47(18) . . . . no C2 C3 C9 C8 -152.38(16) . . . . no C2 C3 C4 C5 -143.17(16) . . . . no C2 C3 C4 O2 -26.43(17) . . . . no O2 C4 C5 C10 72.64(19) . . . . no C3 C4 C5 C6 -43.4(2) . . . . no O2 C4 C5 C6 -158.70(15) . . . . no C3 C4 C5 C10 -172.10(16) . . . . no C4 C5 C10 C11 -167.21(17) . . . . no C6 C5 C10 C11 59.7(2) . . . . no C10 C5 C6 C13 -62.9(2) . . . . no C4 C5 C6 C7 -16.0(3) . . . . no C4 C5 C6 C13 166.21(16) . . . . no C10 C5 C6 C7 114.8(2) . . . . no C13 C6 C7 C8 174.55(17) . . . . no C7 C6 C13 C12 -117.7(2) . . . . no C5 C6 C7 C14 178.35(18) . . . . no C13 C6 C7 C14 -4.2(3) . . . . no C5 C6 C7 C8 -2.9(3) . . . . no C5 C6 C13 C12 60.2(2) . . . . no C6 C7 C8 C9 68.0(2) . . . . no C14 C7 C8 C9 -113.1(2) . . . . no C7 C8 C9 O3 65.8(2) . . . . no C7 C8 C9 C3 -51.0(2) . . . . no C5 C10 C11 C12 -53.9(2) . . . . no C10 C11 C12 C13 50.9(2) . . . . no C11 C12 C13 C6 -54.2(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C1 3.351(3) . 3_554 no O1 C2 3.291(3) . 3_554 no O4 C8 3.167(3) . . no O4 C1 3.308(3) . 1_455 no O4 C3 3.418(2) . 1_455 no O1 H4 2.8500 . 3_554 no O1 H2B 2.6500 . 3_554 no O2 H10A 2.7200 . . no O2 H13B 2.7400 . 4_454 no O3 H16B 2.9200 . 3_544 no O4 H3 2.7000 . 1_455 no O4 H8A 2.6300 . . no O4 H9 2.5400 . . no O4 H12B 2.8900 . 2_354 no C1 O4 3.308(3) . 1_655 no C1 O1 3.351(3) . 3_454 no C2 O1 3.291(3) . 3_454 no C3 O4 3.418(2) . 1_655 no C8 O4 3.167(3) . . no C12 C15 3.508(3) . 2_355 no C15 C12 3.508(3) . 2_354 no C2 H14C 2.8600 . 2_354 no C4 H8B 2.5900 . . no C5 H8B 2.9600 . . no C6 H3 2.8000 . . no C7 H3 2.9500 . . no C8 H4 2.6100 . . no C10 H14A 3.0000 . 4_454 no C11 H16C 3.0600 . 4_454 no C12 H5 3.0800 . . no C13 H14C 2.9800 . . no C13 H10A 2.8600 . 4_444 no C13 H14A 3.0300 . . no C14 H10A 2.9400 . 4_444 no C14 H13B 2.6000 . . no C15 H8A 2.8000 . . no C15 H12B 3.0600 . 2_354 no C16 H2A 2.9500 . 3_444 no C16 H12A 3.0700 . 4_344 no H2A H14C 2.5300 . 2_354 no H2A C16 2.9500 . 3_544 no H2B H9 2.3500 . . no H2B O1 2.6500 . 3_454 no H3 O4 2.7000 . 1_655 no H3 C6 2.8000 . . no H3 C7 2.9500 . . no H3 H5 2.5100 . . no H4 C8 2.6100 . . no H4 H8B 2.0900 . . no H4 O1 2.8500 . 3_454 no H5 C12 3.0800 . . no H5 H3 2.5100 . . no H5 H8A 2.3500 . 1_655 no H5 H11A 2.4800 . . no H5 H13A 2.3400 . . no H8A O4 2.6300 . . no H8A C15 2.8000 . . no H8A H5 2.3500 . 1_455 no H8A H14B 2.0800 . . no H8B C4 2.5900 . . no H8B C5 2.9600 . . no H8B H4 2.0900 . . no H9 O4 2.5400 . . no H9 H2B 2.3500 . . no H10A O2 2.7200 . . no H10A C13 2.8600 . 4_454 no H10A C14 2.9400 . 4_454 no H10A H13B 2.5200 . 4_454 no H10A H14A 2.1300 . 4_454 no H11A H5 2.4800 . . no H11A H16C 2.5300 . 4_454 no H12A C16 3.0700 . 4_354 no H12A H16B 2.2800 . 4_354 no H12B O4 2.8900 . 2_355 no H12B C15 3.0600 . 2_355 no H13A H5 2.3400 . . no H13A H14B 2.5300 . 1_655 no H13B C14 2.6000 . . no H13B H14A 2.4600 . . no H13B H14C 2.3900 . . no H13B O2 2.7400 . 4_444 no H13B H10A 2.5200 . 4_444 no H14A C13 3.0300 . . no H14A H13B 2.4600 . . no H14A C10 3.0000 . 4_444 no H14A H10A 2.1300 . 4_444 no H14B H8A 2.0800 . . no H14B H13A 2.5300 . 1_455 no H14C C13 2.9800 . . no H14C H13B 2.3900 . . no H14C C2 2.8600 . 2_355 no H14C H2A 2.5300 . 2_355 no H16A H16B 2.4600 . 3_544 no H16B O3 2.9200 . 3_444 no H16B H16A 2.4600 . 3_444 no H16B H12A 2.2800 . 4_344 no H16C C11 3.0600 . 4_444 no H16C H11A 2.5300 . 4_444 no #===END # Attachment '- 16.cif' # CIF-file generated for Schanderl Scm 149 #============================================================================== data_j025 _database_code_depnum_ccdc_archive 'CCDC 798361' #TrackingRef '- 16.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H22 O4' _chemical_formula_iupac ? _chemical_formula_weight 278.34 _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 'C 2y' _symmetry_space_group_name_H-M 'C 2' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z 3 1/2+x,1/2+y,z 4 1/2-x,1/2+y,-z _cell_length_a 17.9518(3) _cell_length_b 8.62335(15) _cell_length_c 9.25071(15) _cell_angle_alpha 90 _cell_angle_beta 96.1609(15) _cell_angle_gamma 90 _cell_volume 1423.78(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 4295 _cell_measurement_theta_min 4.8042 _cell_measurement_theta_max 76.0817 _cell_special_details ; ; _exptl_crystal_description 'flat parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3052 _exptl_crystal_size_mid 0.1169 _exptl_crystal_size_min 0.0594 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.750 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.857 _exptl_absorpt_correction_T_max 0.958 #=============================================================================== # 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_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -117.00 -45.00 1.2000 2.0000 omega____ theta____ kappa____ phi______ frames - -41.0814 -169.0000 -44.0000 60 #__ type_ start__ end____ width___ exp.time_ 2 omega -117.00 -21.00 1.2000 2.0000 omega____ theta____ kappa____ phi______ frames - -41.0814 -38.0000 0.0000 80 #__ type_ start__ end____ width___ exp.time_ 3 omega -46.00 -6.40 1.2000 2.0000 omega____ theta____ kappa____ phi______ frames - -41.0814 125.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 4 omega -123.00 -47.40 1.2000 2.0000 omega____ theta____ kappa____ phi______ frames - -41.0814 -169.0000 27.0000 63 #__ type_ start__ end____ width___ exp.time_ 5 omega 13.00 109.00 1.2000 2.0000 omega____ theta____ kappa____ phi______ frames - 41.0814 77.0000 90.0000 80 #__ type_ start__ end____ width___ exp.time_ 6 omega -78.00 -51.60 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 90.0000 22 #__ type_ start__ end____ width___ exp.time_ 7 omega -76.00 -49.60 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 60.0000 22 #__ type_ start__ end____ width___ exp.time_ 8 omega -76.00 -49.60 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 30.0000 22 #__ type_ start__ end____ width___ exp.time_ 9 omega -103.80 -51.00 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -71.0000 -5.0000 44 #__ type_ start__ end____ width___ exp.time_ 10 omega 37.00 109.00 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -115.0000 99.0000 60 #__ type_ start__ end____ width___ exp.time_ 11 omega 46.00 76.00 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega 38.00 72.80 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -60.0000 29 #__ type_ start__ end____ width___ exp.time_ 13 omega 79.00 154.60 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 60.0000 63 #__ type_ start__ end____ width___ exp.time_ 14 omega 41.00 69.80 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -90.0000 24 #__ type_ start__ end____ width___ exp.time_ 15 omega 86.00 156.80 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 0.0000 59 #__ type_ start__ end____ width___ exp.time_ 16 omega 81.00 129.00 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 30.0000 40 #__ type_ start__ end____ width___ exp.time_ 17 omega 54.00 157.20 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 15.0000 -150.0000 86 #__ type_ start__ end____ width___ exp.time_ 18 omega 79.00 141.40 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 90.0000 52 #__ type_ start__ end____ width___ exp.time_ 19 omega 89.00 155.00 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 20 omega 40.00 60.40 1.2000 8.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -30.0000 17 ; _diffrn_detector_area_resol_mean 10.3546 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 4531 _diffrn_reflns_av_R_equivalents 0.0104 _diffrn_reflns_av_sigmaI/netI 0.0107 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.81 _diffrn_reflns_theta_max 76.27 _diffrn_reflns_theta_full 76.27 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2765 # number of observed reflections (> n sig(I)) _reflns_number_gt 2723 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.4185P] 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 0.03(15) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration syn _refine_ls_number_reflns 2765 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.036 #=============================================================================== # 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 -0.13395(5) -0.37237(11) -0.69220(10) 1.000 0.0249(3) . . O2 O Uani -0.01718(6) -0.40399(16) -0.75332(12) 1.000 0.0419(3) . . O3 O Uani -0.23444(6) -0.54601(13) -0.22265(11) 1.000 0.0324(3) . . O4 O Uani -0.22674(6) -0.29348(12) -0.20816(11) 1.000 0.0308(3) . . C1 C Uani -0.11971(7) 0.01254(15) -0.40493(14) 1.000 0.0223(3) . . C2 C Uani -0.12292(9) 0.15181(16) -0.30661(14) 1.000 0.0304(4) . . C3 C Uani -0.08341(9) 0.13366(18) -0.15188(15) 1.000 0.0317(4) . . C4 C Uani -0.13429(9) 0.06595(19) -0.04665(14) 1.000 0.0319(4) . . C5 C Uani -0.15468(8) -0.10379(17) -0.07444(14) 1.000 0.0279(4) . . C6 C Uani -0.18975(7) -0.14412(15) -0.22832(14) 1.000 0.0231(3) . . C7 C Uani -0.13394(6) -0.14820(15) -0.34409(12) 1.000 0.0201(3) . . C8 C Uani -0.16151(7) -0.26282(15) -0.46554(13) 1.000 0.0211(3) . . C9 C Uani -0.10579(7) -0.26394(15) -0.57765(13) 1.000 0.0218(4) . . C10 C Uani -0.09695(8) -0.10574(17) -0.64483(14) 1.000 0.0252(4) . . C11 C Uani -0.10316(7) 0.02905(15) -0.54277(14) 1.000 0.0231(3) . . C12 C Uani -0.08356(7) -0.42664(17) -0.77698(14) 1.000 0.0270(4) . . C13 C Uani -0.12064(10) -0.51655(18) -0.90349(16) 1.000 0.0339(4) . . C14 C Uani -0.09057(8) 0.18210(17) -0.61510(15) 1.000 0.0294(4) . . C15 C Uani -0.16683(7) -0.42320(17) -0.39956(14) 1.000 0.0254(3) . . C16 C Uani -0.21125(7) -0.42827(17) -0.27107(13) 1.000 0.0249(4) . . H2A H Uiso -0.17620 0.17710 -0.29960 1.000 0.0360 calc R H2B H Uiso -0.10040 0.24120 -0.35300 1.000 0.0360 calc R H3A H Uiso -0.03930 0.06530 -0.15480 1.000 0.0380 calc R H3B H Uiso -0.06520 0.23640 -0.11570 1.000 0.0380 calc R H4A H Uiso -0.18100 0.12770 -0.05270 1.000 0.0380 calc R H4B H Uiso -0.10920 0.07620 0.05350 1.000 0.0380 calc R H5A H Uiso -0.19010 -0.13520 -0.00490 1.000 0.0340 calc R H5B H Uiso -0.10870 -0.16680 -0.05290 1.000 0.0340 calc R H6 H Uiso -0.22920 -0.06540 -0.25860 1.000 0.0280 calc R H7 H Uiso -0.08510 -0.18800 -0.29600 1.000 0.0240 calc R H8 H Uiso -0.21190 -0.23000 -0.51220 1.000 0.0250 calc R H9 H Uiso -0.05600 -0.30060 -0.53120 1.000 0.0260 calc R H10A H Uiso -0.04740 -0.10110 -0.68250 1.000 0.0300 calc R H10B H Uiso -0.13570 -0.09400 -0.72870 1.000 0.0300 calc R H13A H Uiso -0.15570 -0.44910 -0.96260 1.000 0.0410 calc R H13B H Uiso -0.14790 -0.60460 -0.86770 1.000 0.0410 calc R H13C H Uiso -0.08250 -0.55480 -0.96290 1.000 0.0410 calc R H14A H Uiso -0.12890 0.19680 -0.69770 1.000 0.0350 calc R H14B H Uiso -0.09380 0.26640 -0.54500 1.000 0.0350 calc R H14C H Uiso -0.04080 0.18260 -0.64960 1.000 0.0350 calc R H15A H Uiso -0.19010 -0.49450 -0.47520 1.000 0.0300 calc R H15B H Uiso -0.11560 -0.46150 -0.36910 1.000 0.0300 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 0.0263(4) 0.0277(5) 0.0208(4) -0.0076(4) 0.0029(3) -0.0017(3) O2 0.0299(5) 0.0528(7) 0.0445(6) -0.0215(6) 0.0108(4) -0.0015(5) O3 0.0376(5) 0.0297(5) 0.0307(5) 0.0023(4) 0.0070(4) -0.0061(4) O4 0.0350(5) 0.0297(5) 0.0297(5) -0.0053(4) 0.0131(4) -0.0065(4) C1 0.0255(6) 0.0216(6) 0.0197(6) -0.0004(5) 0.0025(4) 0.0035(5) C2 0.0489(8) 0.0209(7) 0.0223(6) -0.0005(5) 0.0087(6) 0.0039(6) C3 0.0443(8) 0.0296(7) 0.0217(6) -0.0071(5) 0.0065(6) -0.0069(6) C4 0.0459(8) 0.0310(8) 0.0196(6) -0.0061(6) 0.0077(5) -0.0025(6) C5 0.0384(7) 0.0287(7) 0.0173(6) -0.0014(5) 0.0058(5) -0.0020(6) C6 0.0265(6) 0.0226(6) 0.0209(6) -0.0014(5) 0.0057(5) 0.0009(5) C7 0.0221(5) 0.0223(6) 0.0158(5) -0.0019(5) 0.0018(4) 0.0012(5) C8 0.0217(5) 0.0244(6) 0.0171(5) -0.0025(5) 0.0011(4) 0.0005(5) C9 0.0225(6) 0.0248(7) 0.0179(6) -0.0052(5) 0.0016(4) -0.0001(5) C10 0.0291(6) 0.0286(7) 0.0187(6) -0.0026(5) 0.0057(4) 0.0000(5) C11 0.0267(6) 0.0220(6) 0.0205(6) -0.0004(5) 0.0022(5) 0.0005(5) C12 0.0322(6) 0.0254(7) 0.0243(6) -0.0049(6) 0.0073(5) -0.0005(6) C13 0.0476(8) 0.0305(8) 0.0243(7) -0.0085(5) 0.0073(6) -0.0043(6) C14 0.0396(7) 0.0267(7) 0.0225(6) 0.0025(5) 0.0055(5) 0.0013(6) C15 0.0294(6) 0.0233(6) 0.0240(6) -0.0025(5) 0.0054(5) -0.0013(6) C16 0.0242(6) 0.0279(7) 0.0222(6) -0.0013(6) 0.0006(5) -0.0022(6) _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 C9 1.4621(16) . . yes O1 C12 1.3434(16) . . yes O2 C12 1.2042(17) . . yes O3 C16 1.2020(18) . . yes O4 C6 1.4701(17) . . yes O4 C16 1.3423(17) . . yes C1 C2 1.5113(19) . . no C1 C7 1.5278(18) . . no C1 C11 1.3475(18) . . no C2 C3 1.5357(19) . . no C3 C4 1.521(2) . . no C4 C5 1.524(2) . . no C5 C6 1.5334(18) . . no C6 C7 1.5435(17) . . no C7 C8 1.5378(17) . . no C8 C9 1.5162(17) . . no C8 C15 1.5189(19) . . no C9 C10 1.5145(19) . . no C10 C11 1.5091(19) . . no C11 C14 1.5077(19) . . no C12 C13 1.499(2) . . no C15 C16 1.5014(18) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C4 H4A 0.9900 . . no C4 H4B 0.9900 . . no C5 H5A 0.9900 . . no C5 H5B 0.9900 . . no C6 H6 1.0000 . . no C7 H7 1.0000 . . no C8 H8 1.0000 . . no C9 H9 1.0000 . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no C15 H15A 0.9900 . . no C15 H15B 0.9900 . . 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 O1 C12 116.35(10) . . . yes C6 O4 C16 125.89(11) . . . yes C2 C1 C7 118.72(11) . . . no C2 C1 C11 120.80(12) . . . no C7 C1 C11 120.47(11) . . . no C1 C2 C3 115.87(12) . . . no C2 C3 C4 112.74(13) . . . no C3 C4 C5 114.24(12) . . . no C4 C5 C6 116.21(11) . . . no O4 C6 C5 103.12(10) . . . yes O4 C6 C7 113.81(10) . . . yes C5 C6 C7 114.64(10) . . . no C1 C7 C6 112.43(10) . . . no C1 C7 C8 111.56(10) . . . no C6 C7 C8 109.85(10) . . . no C7 C8 C9 108.64(10) . . . no C7 C8 C15 108.72(10) . . . no C9 C8 C15 110.10(11) . . . no O1 C9 C8 107.32(10) . . . yes O1 C9 C10 108.78(10) . . . yes C8 C9 C10 112.38(11) . . . no C9 C10 C11 114.77(11) . . . no C1 C11 C10 123.31(12) . . . no C1 C11 C14 124.84(12) . . . no C10 C11 C14 111.84(11) . . . no O1 C12 O2 123.55(13) . . . yes O1 C12 C13 111.44(12) . . . yes O2 C12 C13 125.01(13) . . . yes C8 C15 C16 113.97(12) . . . no O3 C16 O4 118.28(12) . . . yes O3 C16 C15 123.66(13) . . . yes O4 C16 C15 118.06(12) . . . yes C1 C2 H2A 108.00 . . . no C1 C2 H2B 108.00 . . . no C3 C2 H2A 108.00 . . . no C3 C2 H2B 108.00 . . . no H2A C2 H2B 107.00 . . . no C2 C3 H3A 109.00 . . . no C2 C3 H3B 109.00 . . . no C4 C3 H3A 109.00 . . . no C4 C3 H3B 109.00 . . . no H3A C3 H3B 108.00 . . . no C3 C4 H4A 109.00 . . . no C3 C4 H4B 109.00 . . . no C5 C4 H4A 109.00 . . . no C5 C4 H4B 109.00 . . . no H4A C4 H4B 108.00 . . . no C4 C5 H5A 108.00 . . . no C4 C5 H5B 108.00 . . . no C6 C5 H5A 108.00 . . . no C6 C5 H5B 108.00 . . . no H5A C5 H5B 107.00 . . . no O4 C6 H6 108.00 . . . no C5 C6 H6 108.00 . . . no C7 C6 H6 108.00 . . . no C1 C7 H7 108.00 . . . no C6 C7 H7 108.00 . . . no C8 C7 H7 108.00 . . . no C7 C8 H8 110.00 . . . no C9 C8 H8 110.00 . . . no C15 C8 H8 110.00 . . . no O1 C9 H9 109.00 . . . no C8 C9 H9 109.00 . . . no C10 C9 H9 109.00 . . . no C9 C10 H10A 109.00 . . . no C9 C10 H10B 109.00 . . . no C11 C10 H10A 109.00 . . . no C11 C10 H10B 109.00 . . . no H10A C10 H10B 108.00 . . . no C12 C13 H13A 109.00 . . . no C12 C13 H13B 109.00 . . . no C12 C13 H13C 109.00 . . . no H13A C13 H13B 110.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no C11 C14 H14A 109.00 . . . no C11 C14 H14B 109.00 . . . no C11 C14 H14C 109.00 . . . no H14A C14 H14B 109.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no C8 C15 H15A 109.00 . . . no C8 C15 H15B 109.00 . . . no C16 C15 H15A 109.00 . . . no C16 C15 H15B 109.00 . . . no H15A C15 H15B 108.00 . . . 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 O1 C9 C8 -160.11(11) . . . . no C12 O1 C9 C10 78.07(13) . . . . no C9 O1 C12 O2 8.3(2) . . . . no C9 O1 C12 C13 -171.29(11) . . . . no C16 O4 C6 C7 5.82(17) . . . . no C16 O4 C6 C5 -118.98(13) . . . . no C6 O4 C16 O3 164.89(12) . . . . no C6 O4 C16 C15 -16.00(18) . . . . no C11 C1 C7 C8 -25.53(16) . . . . no C2 C1 C7 C6 31.85(15) . . . . no C2 C1 C7 C8 155.77(11) . . . . no C11 C1 C7 C6 -149.46(12) . . . . no C7 C1 C11 C10 -0.46(19) . . . . no C7 C1 C11 C14 177.95(12) . . . . no C11 C1 C2 C3 -134.60(14) . . . . no C7 C1 C2 C3 44.09(18) . . . . no C2 C1 C11 C10 178.21(12) . . . . no C2 C1 C11 C14 -3.4(2) . . . . no C1 C2 C3 C4 -88.32(16) . . . . no C2 C3 C4 C5 69.35(16) . . . . no C3 C4 C5 C6 -54.63(17) . . . . no C4 C5 C6 C7 75.28(15) . . . . no C4 C5 C6 O4 -160.46(12) . . . . no O4 C6 C7 C8 32.98(14) . . . . no C5 C6 C7 C8 151.36(11) . . . . no O4 C6 C7 C1 157.84(10) . . . . no C5 C6 C7 C1 -83.78(13) . . . . no C1 C7 C8 C9 54.46(13) . . . . no C6 C7 C8 C15 -60.36(13) . . . . no C6 C7 C8 C9 179.83(10) . . . . no C1 C7 C8 C15 174.27(10) . . . . no C15 C8 C9 C10 -178.76(10) . . . . no C7 C8 C15 C16 51.95(14) . . . . no C7 C8 C9 C10 -59.81(13) . . . . no C7 C8 C9 O1 -179.36(9) . . . . no C9 C8 C15 C16 170.85(10) . . . . no C15 C8 C9 O1 61.70(12) . . . . no O1 C9 C10 C11 153.31(11) . . . . no C8 C9 C10 C11 34.62(15) . . . . no C9 C10 C11 C14 177.59(11) . . . . no C9 C10 C11 C1 -3.82(19) . . . . no C8 C15 C16 O4 -14.55(16) . . . . no C8 C15 C16 O3 164.51(12) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C10 3.1593(19) . . no O3 C13 3.4147(19) . 1_556 no O3 C10 3.1833(18) . 4_444 no O1 H15A 2.5700 . . no O2 H7 2.6200 . 2_554 no O2 H15B 2.5800 . 2_554 no O2 H10A 2.7600 . . no O2 H9 2.4100 . . no O3 H2A 2.7300 . 1_545 no O3 H13A 2.7800 . 1_556 no O3 H5A 2.7300 . 4_445 no O3 H10B 2.3600 . 4_444 no O4 H8 2.9100 . . no O4 H13A 2.8200 . 1_556 no O4 H14A 2.6500 . 4_444 no C10 O2 3.1593(19) . . no C10 O3 3.1833(18) . 4_454 no C13 O3 3.4147(19) . 1_554 no C2 H6 2.7400 . . no C2 H14B 2.5200 . . no C2 H14C 3.0200 . 2_554 no C3 H14C 3.0700 . 2_554 no C3 H7 3.0800 . . no C6 H2A 2.8600 . . no C7 H3A 2.9500 . . no C9 H9 2.9900 . 2_554 no C11 H8 3.0000 . . no C12 H10A 2.9900 . . no C12 H10B 3.0600 . . no C14 H2B 2.5000 . . no C14 H13B 3.0600 . 1_565 no C16 H7 3.1000 . . no C16 H13A 2.9300 . 1_556 no C16 H10B 3.1000 . 4_444 no C16 H14A 3.0500 . 4_444 no H2A O3 2.7300 . 1_565 no H2A C6 2.8600 . . no H2A H4A 2.3300 . . no H2A H6 2.3500 . . no H2B C14 2.5000 . . no H2B H14B 1.8100 . . no H2B H15B 2.5800 . 1_565 no H2B H14C 2.5800 . 2_554 no H3A C7 2.9500 . . no H3A H5B 2.5900 . . no H3B H13C 2.3300 . 1_566 no H4A H2A 2.3300 . . no H4B H10B 2.5800 . 1_556 no H4B H14A 2.5800 . 1_556 no H5A O3 2.7300 . 4_455 no H5B H3A 2.5900 . . no H5B H7 2.3400 . . no H6 C2 2.7400 . . no H6 H2A 2.3500 . . no H7 C3 3.0800 . . no H7 C16 3.1000 . . no H7 H5B 2.3400 . . no H7 H9 2.4900 . . no H7 H15B 2.5000 . . no H7 O2 2.6200 . 2_554 no H7 H10A 2.5200 . 2_554 no H8 O4 2.9100 . . no H8 C11 3.0000 . . no H9 O2 2.4100 . . no H9 H7 2.4900 . . no H9 H15B 2.3800 . . no H9 C9 2.9900 . 2_554 no H9 H9 2.0300 . 2_554 no H10A O2 2.7600 . . no H10A C12 2.9900 . . no H10A H14C 2.4700 . . no H10A H7 2.5200 . 2_554 no H10B C12 3.0600 . . no H10B H4B 2.5800 . 1_554 no H10B H14A 2.5300 . . no H10B O3 2.3600 . 4_454 no H10B C16 3.1000 . 4_454 no H13A O3 2.7800 . 1_554 no H13A O4 2.8200 . 1_554 no H13A C16 2.9300 . 1_554 no H13B C14 3.0600 . 1_545 no H13B H14A 2.3300 . 1_545 no H13C H3B 2.3300 . 1_544 no H14A H4B 2.5800 . 1_554 no H14A H10B 2.5300 . . no H14A H13B 2.3300 . 1_565 no H14A O4 2.6500 . 4_454 no H14A C16 3.0500 . 4_454 no H14B C2 2.5200 . . no H14B H2B 1.8100 . . no H14C H10A 2.4700 . . no H14C C2 3.0200 . 2_554 no H14C C3 3.0700 . 2_554 no H14C H2B 2.5800 . 2_554 no H15A O1 2.5700 . . no H15B H2B 2.5800 . 1_545 no H15B H7 2.5000 . . no H15B H9 2.3800 . . no H15B O2 2.5800 . 2_554 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 C10 H10B O3 0.9900 2.3600 3.1833(18) 140.00 4_454 yes C15 H15B O2 0.9900 2.5800 3.4550(17) 148.00 2_554 yes #===END