Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_date 'Fri Apr 22 15:49:25 2005' _audit_creation_method 'by teXsan' _publ_contact_author_name 'ProfD Shunsaku Ohta' _publ_contact_author_address ; Kyoto Phamaceutical University Misasagi-nakauchi 5, Yamashina Kyoto 607-8414 JAPAN ; _publ_contact_author_email SOHTA@MB.KYOTO-PHU.AC.JP _publ_section_title ; Novel Stereoconvergent Transformation of 1,2a-Disubstituted 1,2,2a, 8b-Tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones to 1,3-Disubstituted 1,2,4a,9b-Tetrahydrodibenzofuran-4-ols and its Application to the Second-Generation Synthesis of (})-Linderol A ; _publ_section_references ; Molecular Structure Corporation, Rigaku Corporation. (2004). teXsan. Single Crystal Structure Analysis Software. Version 2.0. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; loop_ _publ_author_name 'Shunsaku Ohta' "Tomoki Inaba'" 'Ikuo Kawasaki' 'Sachiko Kosaka' 'Masaki Nagahama' 'Takashi Shimizu' ; M.Yamashita ; #------------------------------------------------------------------------------ data_1 _database_code_depnum_ccdc_archive 'CCDC 250653' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C21 H20 O4 ' _chemical_formula_moiety 'C21 H20 O4 ' _chemical_formula_weight 336.39 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,z x,1/2-y,1/2+z 1/2+x,y,1/2-z _cell_length_a 22.3809(9) _cell_length_b 17.2516(8) _cell_length_c 9.034(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3488.1(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.5 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424.00 _exptl_absorpt_coefficient_mu 0.716 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 0.998 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2982 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_theta_max 60.09 _diffrn_measured_fraction_theta_max 0.9996 _diffrn_reflns_theta_full 60.09 _diffrn_measured_fraction_theta_full 0.9996 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.98 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2597 _reflns_number_gt 2048 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.2055 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2596 _refine_ls_number_parameters 227 _refine_ls_goodness_of_fit_ref 1.934 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.07800(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.41 _refine_diff_density_min -0.39 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.098(9) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.32173(9) 0.1849(1) 0.2586(3) 0.0743(7) Uani 1.00 1 d . . . O(2) O 0.24734(9) 0.3074(1) 0.2078(3) 0.0903(8) Uani 1.00 1 d . . . O(3) O 0.2514(1) 0.4447(2) 0.1068(4) 0.132(1) Uani 1.00 1 d . . . O(4) O 0.3327(1) 0.5145(1) 0.1523(4) 0.127(1) Uani 1.00 1 d . . . C(1) C 0.4290(1) 0.3208(1) 0.3008(3) 0.0502(7) Uani 1.00 1 d . . . C(2) C 0.3958(1) 0.3979(2) 0.2892(3) 0.0642(8) Uani 1.00 1 d . . . C(3) C 0.3327(1) 0.3876(2) 0.2347(3) 0.0657(9) Uani 1.00 1 d . . . C(4) C 0.3031(1) 0.3209(2) 0.2569(3) 0.0637(8) Uani 1.00 1 d . . . C(5) C 0.3271(1) 0.2556(2) 0.3450(3) 0.0605(8) Uani 1.00 1 d . . . C(6) C 0.3704(1) 0.1400(2) 0.2934(3) 0.0618(8) Uani 1.00 1 d . . . C(7) C 0.3767(2) 0.0635(2) 0.2501(4) 0.0763(10) Uani 1.00 1 d . . . C(8) C 0.4291(2) 0.0273(2) 0.2889(4) 0.079(1) Uani 1.00 1 d . . . C(9) C 0.4734(1) 0.0654(2) 0.3646(3) 0.0714(9) Uani 1.00 1 d . . . C(10) C 0.4660(1) 0.1420(2) 0.4078(3) 0.0607(8) Uani 1.00 1 d . . . C(11) C 0.4136(1) 0.1800(1) 0.3725(3) 0.0528(7) Uani 1.00 1 d . . . C(12) C 0.3931(1) 0.2621(1) 0.3930(3) 0.0520(7) Uani 1.00 1 d . . . C(13) C 0.4921(1) 0.3313(1) 0.3571(3) 0.0510(7) Uani 1.00 1 d . . . C(14) C 0.5036(1) 0.3702(2) 0.4877(3) 0.0634(8) Uani 1.00 1 d . . . C(15) C 0.5611(1) 0.3802(2) 0.5393(4) 0.0758(10) Uani 1.00 1 d . . . C(16) C 0.6083(1) 0.3510(2) 0.4615(4) 0.080(1) Uani 1.00 1 d . . . C(17) C 0.5980(1) 0.3116(2) 0.3324(4) 0.0766(10) Uani 1.00 1 d . . . C(18) C 0.5406(1) 0.3017(2) 0.2803(3) 0.0610(8) Uani 1.00 1 d . . . C(19) C 0.3016(2) 0.4499(2) 0.1590(5) 0.094(1) Uani 1.00 1 d . . . C(20) C 0.3031(2) 0.5808(3) 0.075(1) 0.219(3) Uani 1.00 1 d . . . C(21) C 0.3373(3) 0.6349(4) 0.0461(9) 0.177(3) Uani 1.00 1 d . . . H(1) H 0.4319 0.3003 0.2035 0.0602 Uiso 1.00 1 calc . . . H(2) H 0.3948 0.4215 0.3841 0.0769 Uiso 1.00 1 calc . . . H(3) H 0.4167 0.4306 0.2221 0.0769 Uiso 1.00 1 calc . . . H(4) H 0.2330 0.3568 0.1312 0.0960 Uiso 1.00 1 calc . . . H(5) H 0.3034 0.2502 0.4314 0.0725 Uiso 1.00 1 calc . . . H(6) H 0.3463 0.0373 0.1962 0.0914 Uiso 1.00 1 calc . . . H(7) H 0.4348 -0.0255 0.2625 0.0943 Uiso 1.00 1 calc . . . H(8) H 0.5095 0.0391 0.3876 0.0858 Uiso 1.00 1 calc . . . H(9) H 0.4967 0.1681 0.4610 0.0728 Uiso 1.00 1 calc . . . H(10) H 0.3952 0.2756 0.4948 0.0623 Uiso 1.00 1 calc . . . H(11) H 0.4711 0.3906 0.5433 0.0761 Uiso 1.00 1 calc . . . H(12) H 0.5678 0.4076 0.6290 0.0910 Uiso 1.00 1 calc . . . H(13) H 0.6478 0.3578 0.4968 0.0963 Uiso 1.00 1 calc . . . H(14) H 0.6307 0.2909 0.2783 0.0917 Uiso 1.00 1 calc . . . H(15) H 0.5342 0.2742 0.1906 0.0732 Uiso 1.00 1 calc . . . H(16) H 0.2859 0.5625 -0.0133 0.2630 Uiso 1.00 1 calc . . . H(17) H 0.2726 0.6004 0.1389 0.2630 Uiso 1.00 1 calc . . . H(18) H 0.3520 0.6568 0.1344 0.2100 Uiso 1.00 1 calc . . . H(19) H 0.3694 0.6155 -0.0120 0.2100 Uiso 1.00 1 calc . . . H(20) H 0.3160 0.6729 -0.0090 0.2100 Uiso 1.00 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.057(1) 0.063(1) 0.103(2) -0.0070(9) -0.014(1) -0.003(1) O(2) 0.046(1) 0.094(2) 0.131(2) -0.0031(10) -0.016(1) 0.016(1) O(3) 0.066(2) 0.116(2) 0.213(4) 0.011(1) -0.039(2) 0.061(2) O(4) 0.081(2) 0.077(2) 0.223(4) 0.010(1) -0.015(2) 0.057(2) C(1) 0.047(1) 0.054(1) 0.050(1) 0.0000(10) 0.001(1) -0.001(1) C(2) 0.054(2) 0.060(2) 0.078(2) 0.000(1) -0.003(1) 0.004(1) C(3) 0.050(2) 0.067(2) 0.081(2) 0.007(1) -0.002(1) 0.007(1) C(4) 0.040(1) 0.071(2) 0.080(2) 0.003(1) 0.000(1) 0.004(1) C(5) 0.049(1) 0.064(2) 0.069(2) -0.002(1) 0.009(1) 0.004(1) C(6) 0.058(2) 0.059(2) 0.069(2) -0.005(1) 0.000(1) 0.006(1) C(7) 0.086(2) 0.056(2) 0.088(2) -0.012(2) 0.002(2) 0.002(2) C(8) 0.102(3) 0.053(2) 0.081(2) 0.004(2) 0.012(2) 0.007(1) C(9) 0.082(2) 0.065(2) 0.067(2) 0.018(2) 0.009(2) 0.014(1) C(10) 0.068(2) 0.064(2) 0.050(1) 0.007(1) 0.001(1) 0.009(1) C(11) 0.055(1) 0.057(1) 0.046(1) 0.000(1) 0.007(1) 0.006(1) C(12) 0.051(1) 0.058(1) 0.047(1) 0.000(1) 0.002(1) -0.002(1) C(13) 0.046(1) 0.055(1) 0.051(1) -0.003(1) 0.000(1) 0.003(1) C(14) 0.053(1) 0.076(2) 0.061(2) -0.004(1) 0.001(1) -0.009(1) C(15) 0.063(2) 0.094(2) 0.070(2) -0.015(2) -0.011(1) -0.008(2) C(16) 0.049(2) 0.115(3) 0.077(2) -0.009(2) -0.007(1) 0.007(2) C(17) 0.049(2) 0.101(2) 0.079(2) 0.008(1) 0.004(1) 0.005(2) C(18) 0.053(2) 0.070(2) 0.060(2) 0.004(1) 0.000(1) -0.002(1) C(19) 0.062(2) 0.081(2) 0.141(3) 0.011(2) -0.003(2) 0.028(2) C(20) 0.101(3) 0.115(4) 0.44(1) 0.010(3) -0.023(5) 0.142(7) C(21) 0.221(7) 0.122(4) 0.187(6) 0.034(5) -0.001(5) 0.064(4) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SAPI91 _computing_structure_refinement 'teXsan Ver. 2.0' _computing_publication_material 'teXsan Ver. 2.0' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 O(1) C(5) 1.454(4) . . yes O(1) C(6) 1.374(3) . . yes O(2) C(4) 1.345(3) . . yes O(2) H(4) 1.144 . . no O(3) C(19) 1.222(4) . . yes O(4) C(19) 1.314(4) . . yes O(4) C(20) 1.495(6) . . yes C(1) C(2) 1.527(4) . . yes C(1) C(12) 1.537(3) . . yes C(1) C(13) 1.514(3) . . yes C(1) H(1) 0.950 . . no C(2) C(3) 1.507(4) . . yes C(2) H(2) 0.950 . . no C(2) H(3) 0.950 . . no C(3) C(4) 1.342(4) . . yes C(3) C(19) 1.452(4) . . yes C(4) C(5) 1.481(4) . . yes C(5) C(12) 1.542(3) . . yes C(5) H(5) 0.949 . . no C(6) C(7) 1.383(4) . . yes C(6) C(11) 1.386(4) . . yes C(7) C(8) 1.375(5) . . yes C(7) H(6) 0.951 . . no C(8) C(9) 1.373(5) . . yes C(8) H(7) 0.951 . . no C(9) C(10) 1.388(4) . . yes C(9) H(8) 0.950 . . no C(10) C(11) 1.382(4) . . yes C(10) H(9) 0.952 . . no C(11) C(12) 1.500(4) . . yes C(12) H(10) 0.950 . . no C(13) C(14) 1.382(4) . . yes C(13) C(18) 1.385(4) . . yes C(14) C(15) 1.379(4) . . yes C(14) H(11) 0.950 . . no C(15) C(16) 1.366(4) . . yes C(15) H(12) 0.950 . . no C(16) C(17) 1.369(5) . . yes C(16) H(13) 0.949 . . no C(17) C(18) 1.380(4) . . yes C(17) H(14) 0.950 . . no C(18) H(15) 0.950 . . no C(20) C(21) 1.234(8) . . yes C(20) H(16) 0.941 . . no C(20) H(17) 0.958 . . no C(21) H(18) 0.942 . . no C(21) H(19) 0.949 . . no C(21) H(20) 0.952 . . 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 C(5) O(1) C(6) 106.5(2) . . . yes C(4) O(2) H(4) 109.3 . . . no C(19) O(4) C(20) 115.9(4) . . . yes C(2) C(1) C(12) 110.9(2) . . . yes C(2) C(1) C(13) 111.9(2) . . . yes C(2) C(1) H(1) 107.0 . . . no C(12) C(1) C(13) 112.6(2) . . . yes C(12) C(1) H(1) 107.0 . . . no C(13) C(1) H(1) 107.0 . . . no C(1) C(2) C(3) 112.0(2) . . . yes C(1) C(2) H(2) 108.9 . . . no C(1) C(2) H(3) 108.8 . . . no C(3) C(2) H(2) 108.8 . . . no C(3) C(2) H(3) 108.8 . . . no H(2) C(2) H(3) 109.5 . . . no C(2) C(3) C(4) 121.0(3) . . . yes C(2) C(3) C(19) 121.0(3) . . . yes C(4) C(3) C(19) 118.0(3) . . . yes O(2) C(4) C(3) 123.9(3) . . . yes O(2) C(4) C(5) 112.4(2) . . . yes C(3) C(4) C(5) 123.6(3) . . . yes O(1) C(5) C(4) 108.6(2) . . . yes O(1) C(5) C(12) 107.0(2) . . . yes O(1) C(5) H(5) 108.2 . . . no C(4) C(5) C(12) 116.3(2) . . . yes C(4) C(5) H(5) 108.3 . . . no C(12) C(5) H(5) 108.2 . . . no O(1) C(6) C(7) 123.6(3) . . . yes O(1) C(6) C(11) 112.9(2) . . . yes C(7) C(6) C(11) 123.4(3) . . . yes C(6) C(7) C(8) 116.6(3) . . . yes C(6) C(7) H(6) 121.7 . . . no C(8) C(7) H(6) 121.7 . . . no C(7) C(8) C(9) 121.7(3) . . . yes C(7) C(8) H(7) 119.1 . . . no C(9) C(8) H(7) 119.2 . . . no C(8) C(9) C(10) 120.7(3) . . . yes C(8) C(9) H(8) 119.7 . . . no C(10) C(9) H(8) 119.7 . . . no C(9) C(10) C(11) 119.2(3) . . . yes C(9) C(10) H(9) 120.3 . . . no C(11) C(10) H(9) 120.4 . . . no C(6) C(11) C(10) 118.3(2) . . . yes C(6) C(11) C(12) 108.8(2) . . . yes C(10) C(11) C(12) 132.7(2) . . . yes C(1) C(12) C(5) 113.3(2) . . . yes C(1) C(12) C(11) 113.3(2) . . . yes C(1) C(12) H(10) 109.7 . . . no C(5) C(12) C(11) 100.9(2) . . . yes C(5) C(12) H(10) 109.7 . . . no C(11) C(12) H(10) 109.7 . . . no C(1) C(13) C(14) 121.2(2) . . . yes C(1) C(13) C(18) 121.2(2) . . . yes C(14) C(13) C(18) 117.6(2) . . . yes C(13) C(14) C(15) 121.4(3) . . . yes C(13) C(14) H(11) 119.3 . . . no C(15) C(14) H(11) 119.2 . . . no C(14) C(15) C(16) 120.1(3) . . . yes C(14) C(15) H(12) 119.9 . . . no C(16) C(15) H(12) 120.0 . . . no C(15) C(16) C(17) 119.5(3) . . . yes C(15) C(16) H(13) 120.2 . . . no C(17) C(16) H(13) 120.3 . . . no C(16) C(17) C(18) 120.6(3) . . . yes C(16) C(17) H(14) 119.7 . . . no C(18) C(17) H(14) 119.7 . . . no C(13) C(18) C(17) 120.8(3) . . . yes C(13) C(18) H(15) 119.7 . . . no C(17) C(18) H(15) 119.5 . . . no O(3) C(19) O(4) 122.1(3) . . . yes O(3) C(19) C(3) 124.6(3) . . . yes O(4) C(19) C(3) 113.3(3) . . . yes O(4) C(20) C(21) 113.8(5) . . . yes O(4) C(20) H(16) 108.7 . . . no O(4) C(20) H(17) 107.7 . . . no C(21) C(20) H(16) 109.2 . . . no C(21) C(20) H(17) 107.7 . . . no H(16) C(20) H(17) 109.6 . . . no C(20) C(21) H(18) 109.9 . . . no C(20) C(21) H(19) 108.6 . . . no C(20) C(21) H(20) 108.6 . . . no H(18) C(21) H(19) 110.2 . . . no H(18) C(21) H(20) 110.0 . . . no H(19) C(21) H(20) 109.4 . . . 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 O(1) C(5) C(4) O(2) 53.4(3) . . . . yes O(1) C(5) C(4) C(3) -129.6(3) . . . . yes O(1) C(5) C(12) C(1) 102.5(2) . . . . yes O(1) C(5) C(12) C(11) -18.9(3) . . . . yes O(1) C(6) C(7) C(8) 177.5(3) . . . . yes O(1) C(6) C(11) C(10) -176.9(2) . . . . yes O(1) C(6) C(11) C(12) -0.9(3) . . . . yes O(2) C(4) C(3) C(2) -178.2(3) . . . . yes O(2) C(4) C(3) C(19) 2.9(5) . . . . yes O(2) C(4) C(5) C(12) 174.1(2) . . . . yes O(3) C(19) O(4) C(20) -0.8(8) . . . . yes O(3) C(19) C(3) C(2) 177.0(4) . . . . yes O(3) C(19) C(3) C(4) -4.1(6) . . . . yes O(4) C(19) C(3) C(2) -3.6(5) . . . . yes O(4) C(19) C(3) C(4) 175.3(4) . . . . yes C(1) C(2) C(3) C(4) 26.6(4) . . . . yes C(1) C(2) C(3) C(19) -154.6(3) . . . . yes C(1) C(12) C(5) C(4) -19.1(3) . . . . yes C(1) C(12) C(11) C(6) -109.2(2) . . . . yes C(1) C(12) C(11) C(10) 66.0(4) . . . . yes C(1) C(13) C(14) C(15) -179.8(3) . . . . yes C(1) C(13) C(18) C(17) 179.9(3) . . . . yes C(2) C(1) C(12) C(5) 49.0(3) . . . . yes C(2) C(1) C(12) C(11) 163.2(2) . . . . yes C(2) C(1) C(13) C(14) 53.9(3) . . . . yes C(2) C(1) C(13) C(18) -126.7(3) . . . . yes C(2) C(3) C(4) C(5) 5.1(5) . . . . yes C(3) C(2) C(1) C(12) -52.7(3) . . . . yes C(3) C(2) C(1) C(13) -179.4(2) . . . . yes C(3) C(4) C(5) C(12) -9.0(4) . . . . yes C(3) C(19) O(4) C(20) 179.7(5) . . . . yes C(4) C(5) O(1) C(6) 145.6(2) . . . . yes C(4) C(5) C(12) C(11) -140.5(2) . . . . yes C(5) O(1) C(6) C(7) 170.2(3) . . . . yes C(5) O(1) C(6) C(11) -11.8(3) . . . . yes C(5) C(4) C(3) C(19) -173.8(3) . . . . yes C(5) C(12) C(1) C(13) 175.3(2) . . . . yes C(5) C(12) C(11) C(6) 12.2(3) . . . . yes C(5) C(12) C(11) C(10) -172.6(3) . . . . yes C(6) O(1) C(5) C(12) 19.3(3) . . . . yes C(6) C(7) C(8) C(9) -1.0(5) . . . . yes C(6) C(11) C(10) C(9) -0.6(4) . . . . yes C(7) C(6) C(11) C(10) 1.1(4) . . . . yes C(7) C(6) C(11) C(12) 177.1(3) . . . . yes C(7) C(8) C(9) C(10) 1.5(5) . . . . yes C(8) C(7) C(6) C(11) -0.3(4) . . . . yes C(8) C(9) C(10) C(11) -0.6(4) . . . . yes C(9) C(10) C(11) C(12) -175.5(3) . . . . yes C(11) C(12) C(1) C(13) -70.5(3) . . . . yes C(12) C(1) C(13) C(14) -71.9(3) . . . . yes C(12) C(1) C(13) C(18) 107.6(3) . . . . yes C(13) C(14) C(15) C(16) -0.5(5) . . . . yes C(13) C(18) C(17) C(16) 0.1(5) . . . . yes C(14) C(13) C(18) C(17) -0.6(4) . . . . yes C(14) C(15) C(16) C(17) 0.0(5) . . . . yes C(15) C(14) C(13) C(18) 0.8(4) . . . . yes C(15) C(16) C(17) C(18) 0.2(5) . . . . yes C(19) O(4) C(20) C(21) -167.0(8) . . . . yes C(19) O(4) C(20) C(21) -167.0(8) . . . . yes #------------------------------------------------------------------------------ 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 O(2) C(17) 3.362(4) . 8_455 ? O(2) C(16) 3.549(4) . 8_455 ? C(9) C(9) 3.535(6) . 5_656 ? C(17) C(21) 3.549(9) . 3_645 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(2) H(4) O(3) . . . 1.144 1.587 2.540(3) 136.366 no #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_4 _database_code_depnum_ccdc_archive 'CCDC 257344' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C20 H18 O4 ' _chemical_formula_moiety 'C20 H18 O4 ' _chemical_formula_weight 322.36 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z 1/2-x,1/2+y,1/2+z 1/2+x,1/2-y,z _cell_length_a 8.471(1) _cell_length_b 11.811(2) _cell_length_c 16.531(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1653.9(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.4 _cell_measurement_theta_max 29.9 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.250 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680.00 _exptl_absorpt_coefficient_mu 0.733 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.985 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1460 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 60.06 _diffrn_measured_fraction_theta_max 0.9992 _diffrn_reflns_theta_full 60.06 _diffrn_measured_fraction_theta_full 0.9992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.30 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1283 _reflns_number_gt 1178 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1894 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1283 _refine_ls_number_parameters 218 _refine_ls_goodness_of_fit_ref 1.744 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.10000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.25 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 0 Friedel Pairs' _refine_ls_abs_structure_Flack 0.9(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.9639(3) 0.5974(2) 0.7560(9) 0.0736(7) Uani 1.00 1 d . . . O(2) O 0.9934(5) 0.5237(3) 0.6362(9) 0.095(1) Uani 1.00 1 d . . . O(3) O 0.5741(5) 0.4140(3) 0.6176(9) 0.110(1) Uani 1.00 1 d . . . O(4) O 0.6262(4) 0.5885(3) 0.6632(9) 0.097(1) Uani 1.00 1 d . . . C(1) C 0.8486(4) 0.3218(3) 0.8045(8) 0.0631(8) Uani 1.00 1 d . . . C(2) C 0.8367(5) 0.3195(3) 0.7111(9) 0.0751(10) Uani 1.00 1 d . . . C(3) C 0.7845(4) 0.4440(3) 0.7131(8) 0.0660(8) Uani 1.00 1 d . . . C(4) C 0.9211(4) 0.5232(3) 0.6980(8) 0.0677(9) Uani 1.00 1 d . . . C(5) C 0.8850(4) 0.6074(3) 0.8299(9) 0.0646(8) Uani 1.00 1 d . . . C(6) C 0.9292(6) 0.7004(3) 0.8756(9) 0.082(1) Uani 1.00 1 d . . . C(7) C 0.8607(7) 0.7144(4) 0.9509(9) 0.090(1) Uani 1.00 1 d . . . C(8) C 0.7461(7) 0.6391(4) 0.9769(8) 0.085(1) Uani 1.00 1 d . . . C(9) C 0.7044(6) 0.5472(3) 0.9296(8) 0.075(1) Uani 1.00 1 d . . . C(10) C 0.7766(4) 0.5281(3) 0.8555(8) 0.0608(8) Uani 1.00 1 d . . . C(11) C 0.7414(4) 0.4304(3) 0.8029(8) 0.0577(8) Uani 1.00 1 d . . . C(12) C 0.7954(4) 0.2200(3) 0.8519(8) 0.0621(8) Uani 1.00 1 d . . . C(13) C 0.8004(5) 0.1132(3) 0.8174(8) 0.0697(10) Uani 1.00 1 d . . . C(14) C 0.7523(5) 0.0194(3) 0.8632(9) 0.079(1) Uani 1.00 1 d . . . C(15) C 0.6960(6) 0.0321(3) 0.9390(9) 0.081(1) Uani 1.00 1 d . . . C(16) C 0.6882(7) 0.1378(4) 0.9731(8) 0.089(1) Uani 1.00 1 d . . . C(17) C 0.7396(7) 0.2310(3) 0.9290(8) 0.082(1) Uani 1.00 1 d . . . C(18) C 0.6490(5) 0.4774(4) 0.6583(9) 0.0741(9) Uani 1.00 1 d . . . C(19) C 0.4975(7) 0.6389(7) 0.6159(9) 0.125(2) Uani 1.00 1 d . . . C(20) C 0.3512(7) 0.6421(6) 0.6571(9) 0.119(2) Uani 1.00 1 d . . . H(1) H 0.9528 0.3420 0.8195 0.0758 Uiso 1.00 1 calc . . . H(2) H 0.7599 0.2687 0.6862 0.0910 Uiso 1.00 1 calc . . . H(3) H 0.9345 0.3072 0.6798 0.0910 Uiso 1.00 1 calc . . . H(4) H 1.0044 0.7532 0.8551 0.0985 Uiso 1.00 1 calc . . . H(5) H 0.8936 0.7757 0.9800 0.1091 Uiso 1.00 1 calc . . . H(6) H 0.6958 0.6506 1.0270 0.1026 Uiso 1.00 1 calc . . . H(7) H 0.6253 0.4965 0.9475 0.0899 Uiso 1.00 1 calc . . . H(8) H 0.6335 0.4095 0.8076 0.0692 Uiso 1.00 1 calc . . . H(9) H 0.8361 0.1036 0.7627 0.0836 Uiso 1.00 1 calc . . . H(10) H 0.7595 -0.0543 0.8399 0.0949 Uiso 1.00 1 calc . . . H(11) H 0.6617 -0.0321 0.9682 0.0976 Uiso 1.00 1 calc . . . H(12) H 0.6480 0.1473 1.0257 0.1073 Uiso 1.00 1 calc . . . H(13) H 0.7358 0.3040 0.9524 0.0986 Uiso 1.00 1 calc . . . H(14) H 0.5264 0.7142 0.6016 0.1496 Uiso 1.00 1 calc . . . H(15) H 0.4843 0.5958 0.5672 0.1496 Uiso 1.00 1 calc . . . H(16) H 0.3625 0.6843 0.7051 0.1425 Uiso 1.00 1 calc . . . H(17) H 0.2742 0.6771 0.6230 0.1425 Uiso 1.00 1 calc . . . H(18) H 0.3188 0.5672 0.6690 0.1425 Uiso 1.00 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.062(1) 0.084(1) 0.075(1) -0.016(1) -0.001(1) 0.005(1) O(2) 0.081(2) 0.132(3) 0.073(2) -0.022(2) 0.017(1) 0.009(2) O(3) 0.089(2) 0.140(3) 0.101(2) -0.027(2) -0.038(2) -0.019(2) O(4) 0.087(2) 0.108(2) 0.095(2) 0.026(2) -0.031(2) 0.005(2) C(1) 0.051(2) 0.061(2) 0.078(2) -0.001(1) -0.004(2) 0.001(2) C(2) 0.068(2) 0.081(2) 0.077(2) 0.006(2) 0.006(2) -0.002(2) C(3) 0.055(2) 0.076(2) 0.067(2) -0.002(1) -0.005(1) 0.009(2) C(4) 0.054(2) 0.086(2) 0.063(1) -0.001(1) -0.006(1) 0.012(1) C(5) 0.053(2) 0.068(2) 0.073(2) 0.001(1) -0.008(1) 0.008(1) C(6) 0.086(3) 0.063(2) 0.097(2) -0.004(2) -0.019(2) 0.001(2) C(7) 0.097(3) 0.078(2) 0.096(3) 0.011(2) -0.021(2) -0.015(2) C(8) 0.093(3) 0.082(2) 0.081(3) 0.022(2) 0.000(2) -0.015(2) C(9) 0.078(3) 0.076(2) 0.071(2) 0.007(2) 0.007(2) 0.006(2) C(10) 0.053(2) 0.059(1) 0.071(2) 0.007(1) -0.004(1) 0.007(1) C(11) 0.042(1) 0.063(2) 0.068(2) 0.001(1) -0.003(1) 0.004(1) C(12) 0.048(2) 0.061(1) 0.077(2) 0.005(1) -0.014(2) 0.005(1) C(13) 0.052(2) 0.067(2) 0.090(3) 0.006(1) -0.005(2) -0.006(1) C(14) 0.074(2) 0.062(2) 0.102(2) 0.000(2) -0.010(2) -0.004(2) C(15) 0.085(3) 0.066(2) 0.093(2) -0.005(2) -0.021(2) 0.015(2) C(16) 0.122(4) 0.074(2) 0.072(3) -0.010(3) -0.006(3) 0.010(2) C(17) 0.121(4) 0.060(2) 0.066(2) 0.008(2) -0.009(2) 0.003(2) C(18) 0.055(2) 0.104(2) 0.063(2) -0.001(2) -0.003(1) 0.011(2) C(19) 0.071(2) 0.199(6) 0.104(4) 0.043(4) -0.021(2) 0.033(4) C(20) 0.073(3) 0.158(5) 0.126(5) 0.027(3) -0.002(3) 0.031(4) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SIR88 _computing_structure_refinement 'teXsan Ver. 2.0' _computing_publication_material 'teXsan Ver. 2.0' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 O(1) C(4) 1.348(7) . . yes O(1) C(5) 1.398(8) . . yes O(2) C(4) 1.192(8) . . yes O(3) C(18) 1.190(7) . . yes O(4) C(18) 1.328(7) . . yes O(4) C(19) 1.468(8) . . yes C(1) C(2) 1.548(8) . . yes C(1) C(11) 1.571(6) . . yes C(1) C(12) 1.505(7) . . yes C(1) H(1) 0.947 . . no C(2) C(3) 1.536(8) . . yes C(2) H(2) 0.976 . . no C(2) H(3) 0.987 . . no C(3) C(4) 1.509(7) . . yes C(3) C(11) 1.538(7) . . yes C(3) C(18) 1.514(8) . . yes C(5) C(6) 1.385(8) . . yes C(5) C(10) 1.378(7) . . yes C(6) C(7) 1.38(1) . . yes C(6) H(4) 0.954 . . no C(7) C(8) 1.39(1) . . yes C(7) H(5) 0.912 . . no C(8) C(9) 1.383(8) . . yes C(8) H(6) 0.941 . . no C(9) C(10) 1.388(7) . . yes C(9) H(7) 0.947 . . no C(10) C(11) 1.475(7) . . yes C(11) H(8) 0.949 . . no C(12) C(13) 1.386(7) . . yes C(12) C(17) 1.365(8) . . yes C(13) C(14) 1.402(8) . . yes C(13) H(9) 0.960 . . no C(14) C(15) 1.349(10) . . yes C(14) H(10) 0.954 . . no C(15) C(16) 1.371(9) . . yes C(15) H(11) 0.945 . . no C(16) C(17) 1.390(8) . . yes C(16) H(12) 0.940 . . no C(17) H(13) 0.946 . . no C(19) C(20) 1.41(1) . . yes C(19) H(14) 0.952 . . no C(19) H(15) 0.959 . . no C(20) H(16) 0.941 . . no C(20) H(17) 0.956 . . no C(20) H(18) 0.948 . . 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 C(4) O(1) C(5) 123.2(4) . . . yes C(18) O(4) C(19) 118.4(6) . . . yes C(2) C(1) C(11) 87.8(4) . . . yes C(2) C(1) C(12) 119.1(4) . . . yes C(2) C(1) H(1) 109.1 . . . no C(11) C(1) C(12) 119.2(4) . . . yes C(11) C(1) H(1) 109.7 . . . no C(12) C(1) H(1) 110.1 . . . no C(1) C(2) C(3) 88.8(4) . . . yes C(1) C(2) H(2) 118.3 . . . no C(1) C(2) H(3) 118.0 . . . no C(3) C(2) H(2) 113.9 . . . no C(3) C(2) H(3) 113.2 . . . no H(2) C(2) H(3) 104.4 . . . no C(2) C(3) C(4) 111.7(4) . . . yes C(2) C(3) C(11) 89.4(4) . . . yes C(2) C(3) C(18) 117.1(5) . . . yes C(4) C(3) C(11) 114.0(4) . . . yes C(4) C(3) C(18) 108.7(4) . . . yes C(11) C(3) C(18) 115.1(4) . . . yes O(1) C(4) O(2) 118.0(5) . . . yes O(1) C(4) C(3) 119.5(5) . . . yes O(2) C(4) C(3) 122.5(5) . . . yes O(1) C(5) C(6) 114.5(5) . . . yes O(1) C(5) C(10) 122.0(4) . . . yes C(6) C(5) C(10) 123.5(6) . . . yes C(5) C(6) C(7) 118.2(6) . . . yes C(5) C(6) H(4) 120.4 . . . no C(7) C(6) H(4) 121.4 . . . no C(6) C(7) C(8) 119.8(5) . . . yes C(6) C(7) H(5) 116.2 . . . no C(8) C(7) H(5) 124.0 . . . no C(7) C(8) C(9) 120.5(6) . . . yes C(7) C(8) H(6) 119.8 . . . no C(9) C(8) H(6) 119.7 . . . no C(8) C(9) C(10) 120.9(5) . . . yes C(8) C(9) H(7) 120.0 . . . no C(10) C(9) H(7) 119.0 . . . no C(5) C(10) C(9) 117.0(5) . . . yes C(5) C(10) C(11) 119.1(5) . . . yes C(9) C(10) C(11) 123.9(4) . . . yes C(1) C(11) C(3) 87.9(4) . . . yes C(1) C(11) C(10) 120.8(4) . . . yes C(1) C(11) H(8) 110.1 . . . no C(3) C(11) C(10) 116.0(4) . . . yes C(3) C(11) H(8) 109.5 . . . no C(10) C(11) H(8) 110.5 . . . no C(1) C(12) C(13) 120.3(5) . . . yes C(1) C(12) C(17) 120.9(4) . . . yes C(13) C(12) C(17) 118.8(5) . . . yes C(12) C(13) C(14) 119.2(6) . . . yes C(12) C(13) H(9) 120.3 . . . no C(14) C(13) H(9) 120.4 . . . no C(13) C(14) C(15) 121.1(5) . . . yes C(13) C(14) H(10) 118.9 . . . no C(15) C(14) H(10) 120.0 . . . no C(14) C(15) C(16) 120.0(5) . . . yes C(14) C(15) H(11) 119.5 . . . no C(16) C(15) H(11) 120.5 . . . no C(15) C(16) C(17) 119.4(6) . . . yes C(15) C(16) H(12) 120.4 . . . no C(17) C(16) H(12) 120.3 . . . no C(12) C(17) C(16) 121.5(5) . . . yes C(12) C(17) H(13) 118.7 . . . no C(16) C(17) H(13) 119.8 . . . no O(3) C(18) O(4) 125.3(6) . . . yes O(3) C(18) C(3) 125.3(6) . . . yes O(4) C(18) C(3) 109.3(5) . . . yes O(4) C(19) C(20) 113.9(7) . . . yes O(4) C(19) H(14) 108.7 . . . no O(4) C(19) H(15) 108.5 . . . no C(20) C(19) H(14) 108.6 . . . no C(20) C(19) H(15) 108.5 . . . no H(14) C(19) H(15) 108.5 . . . no C(19) C(20) H(16) 109.3 . . . no C(19) C(20) H(17) 109.0 . . . no C(19) C(20) H(18) 109.2 . . . no H(16) C(20) H(17) 109.7 . . . no H(16) C(20) H(18) 110.4 . . . no H(17) C(20) H(18) 109.1 . . . 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 O(1) C(4) C(3) C(2) -117.9(5) . . . . yes O(1) C(4) C(3) C(11) -18.5(6) . . . . yes O(1) C(4) C(3) C(18) 111.4(5) . . . . yes O(1) C(5) C(6) C(7) -177.7(5) . . . . yes O(1) C(5) C(10) C(9) -179.5(4) . . . . yes O(1) C(5) C(10) C(11) -0.8(6) . . . . yes O(2) C(4) O(1) C(5) 177.8(5) . . . . yes O(2) C(4) C(3) C(2) 62.6(7) . . . . yes O(2) C(4) C(3) C(11) 162.0(5) . . . . yes O(2) C(4) C(3) C(18) -68.1(7) . . . . yes O(3) C(18) O(4) C(19) 0(1) . . . . yes O(3) C(18) C(3) C(2) 4.6(9) . . . . yes O(3) C(18) C(3) C(4) 132.3(6) . . . . yes O(3) C(18) C(3) C(11) -98.4(8) . . . . yes O(4) C(18) C(3) C(2) -175.7(5) . . . . yes O(4) C(18) C(3) C(4) -48.0(6) . . . . yes O(4) C(18) C(3) C(11) 81.2(6) . . . . yes C(1) C(2) C(3) C(4) 96.8(5) . . . . yes C(1) C(2) C(3) C(11) -18.8(4) . . . . yes C(1) C(2) C(3) C(18) -136.9(5) . . . . yes C(1) C(11) C(3) C(2) 18.5(4) . . . . yes C(1) C(11) C(3) C(4) -95.0(5) . . . . yes C(1) C(11) C(3) C(18) 138.3(5) . . . . yes C(1) C(11) C(10) C(5) 84.3(5) . . . . yes C(1) C(11) C(10) C(9) -97.0(6) . . . . yes C(1) C(12) C(13) C(14) 179.1(4) . . . . yes C(1) C(12) C(17) C(16) 179.1(6) . . . . yes C(2) C(1) C(11) C(3) -18.4(4) . . . . yes C(2) C(1) C(11) C(10) -137.7(5) . . . . yes C(2) C(1) C(12) C(13) 27.3(7) . . . . yes C(2) C(1) C(12) C(17) -151.8(5) . . . . yes C(2) C(3) C(11) C(10) 142.1(4) . . . . yes C(3) C(2) C(1) C(11) 18.4(4) . . . . yes C(3) C(2) C(1) C(12) 140.8(4) . . . . yes C(3) C(4) O(1) C(5) -1.7(7) . . . . yes C(3) C(11) C(1) C(12) -140.8(4) . . . . yes C(3) C(11) C(10) C(5) -19.8(6) . . . . yes C(3) C(11) C(10) C(9) 158.8(4) . . . . yes C(3) C(18) O(4) C(19) -178.8(6) . . . . yes C(4) O(1) C(5) C(6) -169.6(5) . . . . yes C(4) O(1) C(5) C(10) 12.6(7) . . . . yes C(4) C(3) C(11) C(10) 28.5(6) . . . . yes C(5) C(6) C(7) C(8) -2.9(9) . . . . yes C(5) C(10) C(9) C(8) -3.1(7) . . . . yes C(6) C(5) C(10) C(9) 3.0(7) . . . . yes C(6) C(5) C(10) C(11) -178.3(5) . . . . yes C(6) C(7) C(8) C(9) 2.8(9) . . . . yes C(7) C(6) C(5) C(10) -0.1(8) . . . . yes C(7) C(8) C(9) C(10) 0.3(9) . . . . yes C(8) C(9) C(10) C(11) 178.2(5) . . . . yes C(10) C(11) C(1) C(12) 99.9(5) . . . . yes C(10) C(11) C(3) C(18) -98.1(5) . . . . yes C(11) C(1) C(12) C(13) 132.4(5) . . . . yes C(11) C(1) C(12) C(17) -46.7(7) . . . . yes C(12) C(13) C(14) C(15) 2.5(8) . . . . yes C(12) C(17) C(16) C(15) 1(1) . . . . yes C(13) C(12) C(17) C(16) 0.0(9) . . . . yes C(13) C(14) C(15) C(16) -1.4(9) . . . . yes C(14) C(13) C(12) C(17) -1.7(7) . . . . yes C(14) C(15) C(16) C(17) 0(1) . . . . yes C(18) O(4) C(19) C(20) 89(1) . . . . yes C(18) O(4) C(19) C(20) 89(1) . . . . yes #------------------------------------------------------------------------------ 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 O(1) C(14) 3.319(7) . 4_555 ? O(2) C(20) 3.36(1) . 1_655 ? O(2) C(16) 3.384(9) . 3_654 ? O(4) C(16) 3.562(9) . 3_654 ? C(5) C(14) 3.497(7) . 4_555 ? C(5) C(15) 3.593(8) . 4_555 ? C(16) C(19) 3.56(1) . 3_645 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_2 _database_code_depnum_ccdc_archive 'CCDC 257345' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C18 H20 O6 ' _chemical_formula_moiety 'C18 H20 O6 ' _chemical_formula_weight 332.35 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.275(1) _cell_length_b 13.425(2) _cell_length_c 7.830(1) _cell_angle_alpha 106.14(1) _cell_angle_beta 114.52(1) _cell_angle_gamma 71.40(1) _cell_volume 828.7(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.7 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352.00 _exptl_absorpt_coefficient_mu 0.836 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.997 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2649 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_max 60.05 _diffrn_measured_fraction_theta_max 1.0028 _diffrn_reflns_theta_full 60.05 _diffrn_measured_fraction_theta_full 1.0028 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.32 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2649 _reflns_number_gt 2138 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.2208 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2471 _refine_ls_number_parameters 218 _refine_ls_goodness_of_fit_ref 1.913 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.10000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.38 _refine_diff_density_min -0.34 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.23(5) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.5113(2) 0.1813(1) 0.1764(2) 0.0617(5) Uani 1.00 1 d . . . O(2) O 0.8170(2) 0.1160(2) 0.1366(3) 0.0786(7) Uani 1.00 1 d . . . O(3) O 1.1122(2) 0.0401(2) 0.3533(3) 0.0806(7) Uani 1.00 1 d . . . O(4) O 1.1869(2) 0.1096(2) 0.6663(3) 0.0723(6) Uani 1.00 1 d . . . O(5) O 0.7280(2) 0.4155(1) 0.8580(2) 0.0603(5) Uani 1.00 1 d . . . O(6) O 0.6946(3) 0.4413(2) 1.1344(3) 0.0818(7) Uani 1.00 1 d . . . C(1) C 0.7054(3) 0.2575(2) 0.6222(3) 0.0508(6) Uani 1.00 1 d . . . C(2) C 0.8853(3) 0.2297(2) 0.6516(4) 0.0637(7) Uani 1.00 1 d . . . C(3) C 0.9173(3) 0.1672(2) 0.4732(4) 0.0594(7) Uani 1.00 1 d . . . C(4) C 0.7985(3) 0.1721(2) 0.3004(4) 0.0598(7) Uani 1.00 1 d . . . C(5) C 0.6349(3) 0.2453(2) 0.2697(3) 0.0570(7) Uani 1.00 1 d . . . C(6) C 0.3844(3) 0.2362(2) 0.2372(3) 0.0540(6) Uani 1.00 1 d . . . C(7) C 0.2337(3) 0.2116(2) 0.1585(3) 0.0638(7) Uani 1.00 1 d . . . C(8) C 0.1173(3) 0.2753(2) 0.2328(4) 0.0726(9) Uani 1.00 1 d . . . C(9) C 0.1490(3) 0.3601(2) 0.3800(4) 0.0726(8) Uani 1.00 1 d . . . C(10) C 0.3026(3) 0.3825(2) 0.4575(4) 0.0661(7) Uani 1.00 1 d . . . C(11) C 0.4222(3) 0.3186(2) 0.3866(3) 0.0523(6) Uani 1.00 1 d . . . C(12) C 0.6013(3) 0.3133(2) 0.4481(3) 0.0531(6) Uani 1.00 1 d . . . C(13) C 0.6752(3) 0.3171(2) 0.8016(3) 0.0552(7) Uani 1.00 1 d . . . C(14) C 0.7327(3) 0.4705(2) 1.0311(3) 0.0576(7) Uani 1.00 1 d . . . C(15) C 0.7945(4) 0.5676(2) 1.0766(4) 0.0765(9) Uani 1.00 1 d . . . C(16) C 1.0786(3) 0.1004(2) 0.4881(4) 0.0669(8) Uani 1.00 1 d . . . C(17) C 1.3548(3) 0.0516(2) 0.6999(5) 0.0741(8) Uani 1.00 1 d . . . C(18) C 1.4499(4) 0.1175(3) 0.6939(5) 0.0810(10) Uani 1.00 1 d . . . H(1) H 0.6752 0.1918 0.5934 0.0610 Uiso 1.00 1 calc . . . H(2) H 0.9444 0.1882 0.7504 0.0765 Uiso 1.00 1 calc . . . H(3) H 0.9214 0.2938 0.6874 0.0765 Uiso 1.00 1 calc . . . H(4) H 0.9137 0.0584 0.1530 0.0380 Uiso 1.00 1 calc . . . H(5) H 0.6179 0.2915 0.1872 0.0685 Uiso 1.00 1 calc . . . H(6) H 0.2115 0.1534 0.0575 0.0765 Uiso 1.00 1 calc . . . H(7) H 0.0123 0.2606 0.1818 0.0871 Uiso 1.00 1 calc . . . H(8) H 0.0662 0.4030 0.4281 0.0872 Uiso 1.00 1 calc . . . H(9) H 0.3249 0.4410 0.5579 0.0794 Uiso 1.00 1 calc . . . H(10) H 0.6196 0.3823 0.4711 0.0638 Uiso 1.00 1 calc . . . H(11) H 0.5622 0.3325 0.7796 0.0662 Uiso 1.00 1 calc . . . H(12) H 0.7347 0.2751 0.8995 0.0662 Uiso 1.00 1 calc . . . H(13) H 0.7253 0.6124 0.9847 0.0919 Uiso 1.00 1 calc . . . H(14) H 0.9018 0.5477 1.0746 0.0919 Uiso 1.00 1 calc . . . H(15) H 0.7960 0.6048 1.1995 0.0919 Uiso 1.00 1 calc . . . H(16) H 1.3577 -0.0101 0.6045 0.0890 Uiso 1.00 1 calc . . . H(17) H 1.4006 0.0308 0.8215 0.0890 Uiso 1.00 1 calc . . . H(18) H 1.4046 0.1385 0.5725 0.0972 Uiso 1.00 1 calc . . . H(19) H 1.5592 0.0780 0.7159 0.0972 Uiso 1.00 1 calc . . . H(20) H 1.4480 0.1791 0.7896 0.0972 Uiso 1.00 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.057(1) 0.068(1) 0.0553(10) -0.0253(8) 0.0147(8) -0.0034(8) O(2) 0.078(1) 0.092(1) 0.066(1) -0.020(1) 0.0331(10) -0.0024(10) O(3) 0.075(1) 0.081(1) 0.088(1) -0.020(1) 0.039(1) -0.004(1) O(4) 0.052(1) 0.075(1) 0.082(1) -0.0199(8) 0.0166(9) 0.0032(9) O(5) 0.071(1) 0.0584(10) 0.0543(10) -0.0298(8) 0.0181(8) 0.0000(8) O(6) 0.117(2) 0.075(1) 0.073(1) -0.042(1) 0.049(1) -0.0074(10) C(1) 0.046(1) 0.055(1) 0.053(1) -0.0235(10) 0.0116(10) 0.0046(9) C(2) 0.051(1) 0.075(2) 0.060(1) -0.025(1) 0.013(1) -0.001(1) C(3) 0.052(1) 0.065(1) 0.065(1) -0.025(1) 0.019(1) 0.004(1) C(4) 0.065(1) 0.065(1) 0.060(1) -0.030(1) 0.026(1) 0.002(1) C(5) 0.060(1) 0.064(1) 0.054(1) -0.027(1) 0.016(1) 0.011(1) C(6) 0.053(1) 0.059(1) 0.049(1) -0.019(1) 0.0092(10) 0.0133(10) C(7) 0.055(1) 0.071(2) 0.059(1) -0.023(1) 0.005(1) 0.013(1) C(8) 0.052(1) 0.090(2) 0.073(2) -0.023(1) 0.006(1) 0.026(1) C(9) 0.053(1) 0.086(2) 0.071(2) -0.005(1) 0.017(1) 0.019(1) C(10) 0.066(2) 0.062(1) 0.063(1) -0.008(1) 0.018(1) 0.010(1) C(11) 0.051(1) 0.052(1) 0.052(1) -0.0152(10) 0.0106(10) 0.0125(9) C(12) 0.058(1) 0.050(1) 0.056(1) -0.024(1) 0.016(1) 0.0067(10) C(13) 0.055(1) 0.057(1) 0.055(1) -0.026(1) 0.012(1) 0.006(1) C(14) 0.058(1) 0.052(1) 0.054(1) -0.015(1) 0.012(1) 0.003(1) C(15) 0.099(2) 0.058(2) 0.071(2) -0.030(1) 0.023(1) 0.003(1) C(16) 0.063(2) 0.062(2) 0.084(2) -0.024(1) 0.030(1) 0.004(1) C(17) 0.059(2) 0.065(2) 0.094(2) -0.013(1) 0.022(1) 0.013(1) C(18) 0.060(2) 0.091(2) 0.097(2) -0.024(1) 0.027(1) 0.014(2) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SIR88 _computing_structure_refinement 'teXsan Ver. 2.0' _computing_publication_material 'teXsan Ver. 2.0' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 O(1) C(5) 1.473(3) . . yes O(1) C(6) 1.368(3) . . yes O(2) C(4) 1.344(3) . . yes O(2) H(4) 0.967 . . no O(3) C(16) 1.226(3) . . yes O(4) C(16) 1.338(3) . . yes O(4) C(17) 1.449(3) . . yes O(5) C(13) 1.445(3) . . yes O(5) C(14) 1.341(3) . . yes O(6) C(14) 1.198(3) . . yes C(1) C(2) 1.520(3) . . yes C(1) C(12) 1.537(3) . . yes C(1) C(13) 1.500(3) . . yes C(1) H(1) 0.950 . . no C(2) C(3) 1.508(4) . . yes C(2) H(2) 0.950 . . no C(2) H(3) 0.950 . . no C(3) C(4) 1.348(4) . . yes C(3) C(16) 1.454(4) . . yes C(4) C(5) 1.484(4) . . yes C(5) C(12) 1.534(3) . . yes C(5) H(5) 0.950 . . no C(6) C(7) 1.381(3) . . yes C(6) C(11) 1.380(3) . . yes C(7) C(8) 1.376(4) . . yes C(7) H(6) 0.950 . . no C(8) C(9) 1.383(4) . . yes C(8) H(7) 0.950 . . no C(9) C(10) 1.393(4) . . yes C(9) H(8) 0.950 . . no C(10) C(11) 1.384(4) . . yes C(10) H(9) 0.950 . . no C(11) C(12) 1.508(3) . . yes C(12) H(10) 0.950 . . no C(13) H(11) 0.950 . . no C(13) H(12) 0.950 . . no C(14) C(15) 1.484(4) . . yes C(15) H(13) 0.950 . . no C(15) H(14) 0.950 . . no C(15) H(15) 0.950 . . no C(17) C(18) 1.456(4) . . yes C(17) H(16) 0.950 . . no C(17) H(17) 0.950 . . no C(18) H(18) 0.950 . . no C(18) H(19) 0.950 . . no C(18) H(20) 0.950 . . 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 C(5) O(1) C(6) 106.0(2) . . . yes C(4) O(2) H(4) 114.3 . . . no C(16) O(4) C(17) 118.6(2) . . . yes C(13) O(5) C(14) 116.2(2) . . . yes C(2) C(1) C(12) 111.2(2) . . . yes C(2) C(1) C(13) 111.5(2) . . . yes C(2) C(1) H(1) 106.5 . . . no C(12) C(1) C(13) 114.1(2) . . . yes C(12) C(1) H(1) 106.5 . . . no C(13) C(1) H(1) 106.5 . . . no C(1) C(2) C(3) 111.8(2) . . . yes C(1) C(2) H(2) 108.9 . . . no C(1) C(2) H(3) 108.9 . . . no C(3) C(2) H(2) 108.9 . . . no C(3) C(2) H(3) 108.9 . . . no H(2) C(2) H(3) 109.5 . . . no C(2) C(3) C(4) 121.0(2) . . . yes C(2) C(3) C(16) 119.5(2) . . . yes C(4) C(3) C(16) 119.5(2) . . . yes O(2) C(4) C(3) 124.1(2) . . . yes O(2) C(4) C(5) 112.6(2) . . . yes C(3) C(4) C(5) 123.2(2) . . . yes O(1) C(5) C(4) 108.5(2) . . . yes O(1) C(5) C(12) 105.6(2) . . . yes O(1) C(5) H(5) 108.6 . . . no C(4) C(5) C(12) 116.7(2) . . . yes C(4) C(5) H(5) 108.6 . . . no C(12) C(5) H(5) 108.6 . . . no O(1) C(6) C(7) 123.7(2) . . . yes O(1) C(6) C(11) 113.2(2) . . . yes C(7) C(6) C(11) 123.1(2) . . . yes C(6) C(7) C(8) 117.0(2) . . . yes C(6) C(7) H(6) 121.5 . . . no C(8) C(7) H(6) 121.5 . . . no C(7) C(8) C(9) 121.7(2) . . . yes C(7) C(8) H(7) 119.1 . . . no C(9) C(8) H(7) 119.1 . . . no C(8) C(9) C(10) 120.0(2) . . . yes C(8) C(9) H(8) 120.0 . . . no C(10) C(9) H(8) 120.0 . . . no C(9) C(10) C(11) 119.2(2) . . . yes C(9) C(10) H(9) 120.4 . . . no C(11) C(10) H(9) 120.4 . . . no C(6) C(11) C(10) 118.9(2) . . . yes C(6) C(11) C(12) 108.0(2) . . . yes C(10) C(11) C(12) 132.9(2) . . . yes C(1) C(12) C(5) 110.8(2) . . . yes C(1) C(12) C(11) 112.6(2) . . . yes C(1) C(12) H(10) 110.9 . . . no C(5) C(12) C(11) 100.3(2) . . . yes C(5) C(12) H(10) 110.9 . . . no C(11) C(12) H(10) 110.9 . . . no O(5) C(13) C(1) 108.8(2) . . . yes O(5) C(13) H(11) 109.6 . . . no O(5) C(13) H(12) 109.6 . . . no C(1) C(13) H(11) 109.6 . . . no C(1) C(13) H(12) 109.6 . . . no H(11) C(13) H(12) 109.5 . . . no O(5) C(14) O(6) 122.7(2) . . . yes O(5) C(14) C(15) 111.5(2) . . . yes O(6) C(14) C(15) 125.7(2) . . . yes C(14) C(15) H(13) 109.5 . . . no C(14) C(15) H(14) 109.5 . . . no C(14) C(15) H(15) 109.5 . . . no H(13) C(15) H(14) 109.5 . . . no H(13) C(15) H(15) 109.5 . . . no H(14) C(15) H(15) 109.5 . . . no O(3) C(16) O(4) 123.1(2) . . . yes O(3) C(16) C(3) 124.0(3) . . . yes O(4) C(16) C(3) 112.8(2) . . . yes O(4) C(17) C(18) 110.8(2) . . . yes O(4) C(17) H(16) 109.1 . . . no O(4) C(17) H(17) 109.1 . . . no C(18) C(17) H(16) 109.1 . . . no C(18) C(17) H(17) 109.1 . . . no H(16) C(17) H(17) 109.5 . . . no C(17) C(18) H(18) 109.5 . . . no C(17) C(18) H(19) 109.5 . . . no C(17) C(18) H(20) 109.5 . . . no H(18) C(18) H(19) 109.5 . . . no H(18) C(18) H(20) 109.5 . . . no H(19) C(18) H(20) 109.5 . . . 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 O(1) C(5) C(4) O(2) 61.0(2) . . . . yes O(1) C(5) C(4) C(3) -122.3(2) . . . . yes O(1) C(5) C(12) C(1) 93.4(2) . . . . yes O(1) C(5) C(12) C(11) -25.7(2) . . . . yes O(1) C(6) C(7) C(8) -178.9(2) . . . . yes O(1) C(6) C(11) C(10) 178.0(2) . . . . yes O(1) C(6) C(11) C(12) -6.0(3) . . . . yes O(2) C(4) C(3) C(2) -177.8(2) . . . . yes O(2) C(4) C(3) C(16) 2.0(4) . . . . yes O(2) C(4) C(5) C(12) -179.9(2) . . . . yes O(3) C(16) O(4) C(17) 4.6(4) . . . . yes O(3) C(16) C(3) C(2) 173.6(2) . . . . yes O(3) C(16) C(3) C(4) -6.1(4) . . . . yes O(4) C(16) C(3) C(2) -5.0(3) . . . . yes O(4) C(16) C(3) C(4) 175.2(2) . . . . yes O(5) C(13) C(1) C(2) 61.0(2) . . . . yes O(5) C(13) C(1) C(12) -66.0(2) . . . . yes O(6) C(14) O(5) C(13) -0.5(4) . . . . yes C(1) C(2) C(3) C(4) 22.7(3) . . . . yes C(1) C(2) C(3) C(16) -157.1(2) . . . . yes C(1) C(12) C(5) C(4) -27.3(2) . . . . yes C(1) C(12) C(11) C(6) -98.2(2) . . . . yes C(1) C(12) C(11) C(10) 77.0(3) . . . . yes C(1) C(13) O(5) C(14) -170.1(2) . . . . yes C(2) C(1) C(12) C(5) 55.0(2) . . . . yes C(2) C(1) C(12) C(11) 166.4(2) . . . . yes C(2) C(3) C(4) C(5) 5.9(4) . . . . yes C(3) C(2) C(1) C(12) -52.9(3) . . . . yes C(3) C(2) C(1) C(13) 178.5(2) . . . . yes C(3) C(4) C(5) C(12) -3.2(3) . . . . yes C(3) C(16) O(4) C(17) -176.8(2) . . . . yes C(4) C(5) O(1) C(6) 149.4(2) . . . . yes C(4) C(5) C(12) C(11) -146.4(2) . . . . yes C(5) O(1) C(6) C(7) 169.0(2) . . . . yes C(5) O(1) C(6) C(11) -11.3(2) . . . . yes C(5) C(4) C(3) C(16) -174.3(2) . . . . yes C(5) C(12) C(1) C(13) -177.9(2) . . . . yes C(5) C(12) C(11) C(6) 19.6(2) . . . . yes C(5) C(12) C(11) C(10) -165.2(3) . . . . yes C(6) O(1) C(5) C(12) 23.6(2) . . . . yes C(6) C(7) C(8) C(9) -0.1(4) . . . . yes C(6) C(11) C(10) C(9) 1.8(4) . . . . yes C(7) C(6) C(11) C(10) -2.3(4) . . . . yes C(7) C(6) C(11) C(12) 173.7(2) . . . . yes C(7) C(8) C(9) C(10) -0.4(4) . . . . yes C(8) C(7) C(6) C(11) 1.4(4) . . . . yes C(8) C(9) C(10) C(11) -0.5(4) . . . . yes C(9) C(10) C(11) C(12) -173.0(2) . . . . yes C(11) C(12) C(1) C(13) -66.4(2) . . . . yes C(13) O(5) C(14) C(15) 177.8(2) . . . . yes C(16) O(4) C(17) C(18) 93.1(3) . . . . yes C(16) O(4) C(17) C(18) 93.1(3) . . . . yes #------------------------------------------------------------------------------ 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 O(1) C(17) 3.235(4) . 2_756 ? O(1) C(18) 3.472(4) . 1_454 ? O(1) C(17) 3.545(4) . 1_454 ? O(3) C(3) 3.545(3) . 2_756 ? O(3) C(8) 3.556(4) . 1_655 ? O(6) C(5) 3.365(3) . 1_556 ? O(6) C(10) 3.402(3) . 2_667 ? O(6) O(6) 3.443(5) . 2_667 ? O(6) C(14) 3.520(3) . 2_667 ? C(16) C(16) 3.526(5) . 2_756 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(2) H(4) O(3) . . . 0.967 1.854 2.595(2) 131.203 no #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_3 _database_code_depnum_ccdc_archive 'CCDC 257506' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C20 H18 O4 ' _chemical_formula_moiety 'C20 H18 O4 ' _chemical_formula_weight 322.36 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 11.759(1) _cell_length_b 9.091(2) _cell_length_c 15.774(1) _cell_angle_alpha 90 _cell_angle_beta 103.766(6) _cell_angle_gamma 90 _cell_volume 1637.8(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.6 _cell_measurement_theta_max 29.9 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680.00 _exptl_absorpt_coefficient_mu 0.741 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.999 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2731 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 60.09 _diffrn_measured_fraction_theta_max 0.9992 _diffrn_reflns_theta_full 60.09 _diffrn_measured_fraction_theta_full 0.9992 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 0 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 4.61 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2539 _reflns_number_gt 1969 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.2411 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2441 _refine_ls_number_parameters 217 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.18400(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.58 _refine_diff_density_min -0.44 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.5416(2) 0.3328(2) 0.4799(1) 0.0541(6) Uani 1.00 1 d . . . O(2) O 0.7064(2) 0.4532(2) 0.5040(1) 0.0653(7) Uani 1.00 1 d . . . O(3) O 0.8519(2) 0.3923(3) 0.7231(2) 0.0913(9) Uani 1.00 1 d . . . O(4) O 0.8481(2) 0.2215(3) 0.6226(2) 0.0703(7) Uani 1.00 1 d . . . C(1) C 0.5846(2) 0.2812(3) 0.7324(2) 0.0456(7) Uani 1.00 1 d . . . C(2) C 0.6064(2) 0.4227(3) 0.6844(2) 0.0506(8) Uani 1.00 1 d . . . C(3) C 0.6682(2) 0.3275(3) 0.6267(2) 0.0435(7) Uani 1.00 1 d . . . C(4) C 0.6434(2) 0.3740(3) 0.5328(2) 0.0463(7) Uani 1.00 1 d . . . C(5) C 0.4661(2) 0.2303(3) 0.5048(2) 0.0435(7) Uani 1.00 1 d . . . C(6) C 0.3638(3) 0.2049(3) 0.4433(2) 0.0571(9) Uani 1.00 1 d . . . C(7) C 0.2867(2) 0.1023(3) 0.4595(2) 0.0592(9) Uani 1.00 1 d . . . C(8) C 0.3120(2) 0.0245(3) 0.5366(2) 0.0540(8) Uani 1.00 1 d . . . C(9) C 0.4136(2) 0.0527(3) 0.5979(2) 0.0468(7) Uani 1.00 1 d . . . C(10) C 0.4938(2) 0.1582(3) 0.5840(2) 0.0402(7) Uani 1.00 1 d . . . C(11) C 0.6020(2) 0.1909(3) 0.6515(2) 0.0397(7) Uani 1.00 1 d . . . C(12) C 0.4757(2) 0.2651(3) 0.7656(2) 0.0485(8) Uani 1.00 1 d . . . C(13) C 0.4767(3) 0.1751(3) 0.8366(2) 0.0619(10) Uani 1.00 1 d . . . C(14) C 0.3768(4) 0.1565(4) 0.8680(3) 0.080(1) Uani 1.00 1 d . . . C(15) C 0.2752(3) 0.2291(4) 0.8287(3) 0.076(1) Uani 1.00 1 d . . . C(16) C 0.2729(3) 0.3185(4) 0.7601(3) 0.075(1) Uani 1.00 1 d . . . C(17) C 0.3721(3) 0.3363(4) 0.7272(2) 0.0627(9) Uani 1.00 1 d . . . C(18) C 0.7991(3) 0.3202(3) 0.6635(2) 0.0531(8) Uani 1.00 1 d . . . C(19) C 0.9749(3) 0.2099(5) 0.6505(3) 0.091(1) Uani 1.00 1 d . . . C(20) C 1.0190(5) 0.1364(9) 0.5885(4) 0.152(3) Uani 1.00 1 d . . . H(1) H 0.6515 0.2648 0.7798 0.0380 Uiso 1.00 1 calc . . . H(2) H 0.6597 0.4816 0.7264 0.0380 Uiso 1.00 1 calc . . . H(3) H 0.5381 0.4649 0.6488 0.0380 Uiso 1.00 1 calc . . . H(4) H 0.3420 0.2532 0.3869 0.0380 Uiso 1.00 1 calc . . . H(5) H 0.2159 0.0790 0.4161 0.0380 Uiso 1.00 1 calc . . . H(6) H 0.2563 -0.0468 0.5470 0.0380 Uiso 1.00 1 calc . . . H(7) H 0.4368 -0.0078 0.6498 0.0380 Uiso 1.00 1 calc . . . H(8) H 0.6522 0.1057 0.6673 0.0380 Uiso 1.00 1 calc . . . H(9) H 0.5503 0.1367 0.8685 0.0380 Uiso 1.00 1 calc . . . H(10) H 0.3873 0.0980 0.9194 0.0380 Uiso 1.00 1 calc . . . H(11) H 0.2071 0.2052 0.8486 0.0380 Uiso 1.00 1 calc . . . H(12) H 0.2036 0.3697 0.7307 0.0380 Uiso 1.00 1 calc . . . H(13) H 0.3689 0.3911 0.6747 0.0380 Uiso 1.00 1 calc . . . H(14) H 0.9955 0.1550 0.7031 0.1119 Uiso 1.00 1 calc . . . H(15) H 1.0077 0.3059 0.6602 0.1119 Uiso 1.00 1 calc . . . H(16) H 1.1023 0.1345 0.6078 0.1953 Uiso 1.00 1 calc . . . H(17) H 0.9999 0.1960 0.5355 0.1953 Uiso 1.00 1 calc . . . H(18) H 0.9873 0.0451 0.5783 0.1953 Uiso 1.00 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.064(1) 0.058(1) 0.037(1) -0.0070(9) 0.0063(9) 0.0087(8) O(2) 0.074(1) 0.071(1) 0.059(1) -0.011(1) 0.031(1) 0.006(1) O(3) 0.063(1) 0.124(2) 0.081(2) -0.030(1) 0.007(1) -0.046(2) O(4) 0.042(1) 0.086(2) 0.079(2) 0.001(1) 0.006(1) -0.020(1) C(1) 0.046(1) 0.055(2) 0.035(1) -0.004(1) 0.007(1) -0.002(1) C(2) 0.064(2) 0.048(1) 0.041(1) -0.007(1) 0.016(1) -0.007(1) C(3) 0.049(2) 0.042(1) 0.040(1) -0.005(1) 0.012(1) -0.003(1) C(4) 0.057(2) 0.041(1) 0.045(1) -0.001(1) 0.020(1) -0.003(1) C(5) 0.052(2) 0.041(1) 0.037(1) 0.001(1) 0.009(1) 0.000(1) C(6) 0.064(2) 0.058(2) 0.040(2) 0.001(1) -0.006(1) 0.003(1) C(7) 0.047(2) 0.063(2) 0.056(2) -0.001(1) -0.011(1) -0.008(1) C(8) 0.047(1) 0.053(2) 0.060(2) -0.007(1) 0.008(1) -0.005(1) C(9) 0.051(2) 0.047(1) 0.041(1) -0.004(1) 0.008(1) 0.003(1) C(10) 0.044(1) 0.040(1) 0.035(1) 0.002(1) 0.006(1) -0.0035(10) C(11) 0.042(1) 0.042(1) 0.033(1) 0.0000(10) 0.005(1) 0.0002(10) C(12) 0.057(2) 0.054(2) 0.036(1) -0.008(1) 0.014(1) -0.008(1) C(13) 0.074(2) 0.065(2) 0.051(2) 0.002(1) 0.023(2) 0.002(1) C(14) 0.113(3) 0.076(2) 0.068(2) -0.012(2) 0.057(2) 0.000(2) C(15) 0.074(2) 0.082(2) 0.084(3) -0.016(2) 0.044(2) -0.020(2) C(16) 0.052(2) 0.094(3) 0.082(2) -0.004(2) 0.020(2) -0.014(2) C(17) 0.055(2) 0.078(2) 0.053(2) -0.003(1) 0.009(1) 0.000(1) C(18) 0.051(2) 0.062(2) 0.045(2) -0.014(1) 0.008(1) -0.004(1) C(19) 0.042(2) 0.126(3) 0.103(3) -0.001(2) 0.012(2) -0.004(3) C(20) 0.075(3) 0.261(8) 0.119(5) 0.039(4) 0.022(3) -0.043(5) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SAPI91 _computing_structure_refinement 'teXsan Ver. 2.0' _computing_publication_material 'teXsan Ver. 2.0' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 O(1) C(4) 1.339(3) . . yes O(1) C(5) 1.407(3) . . yes O(2) C(4) 1.196(3) . . yes O(3) C(18) 1.192(4) . . yes O(4) C(18) 1.316(4) . . yes O(4) C(19) 1.455(4) . . yes C(1) C(2) 1.545(4) . . yes C(1) C(11) 1.570(4) . . yes C(1) C(12) 1.503(4) . . yes C(1) H(1) 0.959 . . no C(2) C(3) 1.555(4) . . yes C(2) H(2) 0.960 . . no C(2) H(3) 0.945 . . no C(3) C(4) 1.502(4) . . yes C(3) C(11) 1.563(3) . . yes C(3) C(18) 1.511(4) . . yes C(5) C(6) 1.374(4) . . yes C(5) C(10) 1.380(4) . . yes C(6) C(7) 1.366(4) . . yes C(6) H(4) 0.970 . . no C(7) C(8) 1.377(4) . . yes C(7) H(5) 0.967 . . no C(8) C(9) 1.370(4) . . yes C(8) H(6) 0.963 . . no C(9) C(10) 1.397(4) . . yes C(9) H(7) 0.970 . . no C(10) C(11) 1.482(3) . . yes C(11) H(8) 0.970 . . no C(12) C(13) 1.385(4) . . yes C(12) C(17) 1.385(4) . . yes C(13) C(14) 1.390(5) . . yes C(13) H(9) 0.957 . . no C(14) C(15) 1.376(6) . . yes C(14) H(10) 0.952 . . no C(15) C(16) 1.349(6) . . yes C(15) H(11) 0.952 . . no C(16) C(17) 1.395(5) . . yes C(16) H(12) 0.956 . . no C(17) H(13) 0.960 . . no C(19) C(20) 1.384(8) . . yes C(19) H(14) 0.948 . . no C(19) H(15) 0.951 . . no C(20) H(16) 0.954 . . no C(20) H(17) 0.976 . . no C(20) H(18) 0.909 . . 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 C(4) O(1) C(5) 122.7(2) . . . yes C(18) O(4) C(19) 115.9(3) . . . yes C(2) C(1) C(11) 88.2(2) . . . yes C(2) C(1) C(12) 120.4(2) . . . yes C(2) C(1) H(1) 108.1 . . . no C(11) C(1) C(12) 121.3(2) . . . yes C(11) C(1) H(1) 108.2 . . . no C(12) C(1) H(1) 108.7 . . . no C(1) C(2) C(3) 88.7(2) . . . yes C(1) C(2) H(2) 106.5 . . . no C(1) C(2) H(3) 114.4 . . . no C(3) C(2) H(2) 113.2 . . . no C(3) C(2) H(3) 109.1 . . . no H(2) C(2) H(3) 120.5 . . . no C(2) C(3) C(4) 114.4(2) . . . yes C(2) C(3) C(11) 88.1(2) . . . yes C(2) C(3) C(18) 112.0(2) . . . yes C(4) C(3) C(11) 118.6(2) . . . yes C(4) C(3) C(18) 109.4(2) . . . yes C(11) C(3) C(18) 113.0(2) . . . yes O(1) C(4) O(2) 118.2(2) . . . yes O(1) C(4) C(3) 118.1(2) . . . yes O(2) C(4) C(3) 123.5(3) . . . yes O(1) C(5) C(6) 114.8(2) . . . yes O(1) C(5) C(10) 122.7(2) . . . yes C(6) C(5) C(10) 122.5(3) . . . yes C(5) C(6) C(7) 119.4(3) . . . yes C(5) C(6) H(4) 124.6 . . . no C(7) C(6) H(4) 116.0 . . . no C(6) C(7) C(8) 120.1(2) . . . yes C(6) C(7) H(5) 121.0 . . . no C(8) C(7) H(5) 118.7 . . . no C(7) C(8) C(9) 119.7(3) . . . yes C(7) C(8) H(6) 118.9 . . . no C(9) C(8) H(6) 121.3 . . . no C(8) C(9) C(10) 121.7(2) . . . yes C(8) C(9) H(7) 120.8 . . . no C(10) C(9) H(7) 117.1 . . . no C(5) C(10) C(9) 116.4(2) . . . yes C(5) C(10) C(11) 122.1(2) . . . yes C(9) C(10) C(11) 121.4(2) . . . yes C(1) C(11) C(3) 87.5(2) . . . yes C(1) C(11) C(10) 115.7(2) . . . yes C(1) C(11) H(8) 113.4 . . . no C(3) C(11) C(10) 112.0(2) . . . yes C(3) C(11) H(8) 113.0 . . . no C(10) C(11) H(8) 113.0 . . . no C(1) C(12) C(13) 119.7(3) . . . yes C(1) C(12) C(17) 122.4(2) . . . yes C(13) C(12) C(17) 117.9(3) . . . yes C(12) C(13) C(14) 120.9(3) . . . yes C(12) C(13) H(9) 118.3 . . . no C(14) C(13) H(9) 120.3 . . . no C(13) C(14) C(15) 119.9(3) . . . yes C(13) C(14) H(10) 114.9 . . . no C(15) C(14) H(10) 125.0 . . . no C(14) C(15) C(16) 120.0(3) . . . yes C(14) C(15) H(11) 116.8 . . . no C(16) C(15) H(11) 123.0 . . . no C(15) C(16) C(17) 120.7(3) . . . yes C(15) C(16) H(12) 122.2 . . . no C(17) C(16) H(12) 117.1 . . . no C(12) C(17) C(16) 120.6(3) . . . yes C(12) C(17) H(13) 118.1 . . . no C(16) C(17) H(13) 121.1 . . . no O(3) C(18) O(4) 123.7(3) . . . yes O(3) C(18) C(3) 124.8(3) . . . yes O(4) C(18) C(3) 111.5(2) . . . yes O(4) C(19) C(20) 110.5(4) . . . yes O(4) C(19) H(14) 109.5 . . . no O(4) C(19) H(15) 109.2 . . . no C(20) C(19) H(14) 107.7 . . . no C(20) C(19) H(15) 110.4 . . . no H(14) C(19) H(15) 109.5 . . . no C(19) C(20) H(16) 108.2 . . . no C(19) C(20) H(17) 106.8 . . . no C(19) C(20) H(18) 111.0 . . . no H(16) C(20) H(17) 107.0 . . . no H(16) C(20) H(18) 112.8 . . . no H(17) C(20) H(18) 110.8 . . . 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 O(1) C(4) C(3) C(2) -79.4(3) . . . . yes O(1) C(4) C(3) C(11) 22.4(3) . . . . yes O(1) C(4) C(3) C(18) 154.0(2) . . . . yes O(1) C(5) C(6) C(7) 177.0(3) . . . . yes O(1) C(5) C(10) C(9) -176.2(2) . . . . yes O(1) C(5) C(10) C(11) 4.3(4) . . . . yes O(2) C(4) O(1) C(5) 174.4(2) . . . . yes O(2) C(4) C(3) C(2) 95.8(3) . . . . yes O(2) C(4) C(3) C(11) -162.4(2) . . . . yes O(2) C(4) C(3) C(18) -30.8(3) . . . . yes O(3) C(18) O(4) C(19) -3.7(5) . . . . yes O(3) C(18) C(3) C(2) -8.8(4) . . . . yes O(3) C(18) C(3) C(4) 119.0(3) . . . . yes O(3) C(18) C(3) C(11) -106.4(3) . . . . yes O(4) C(18) C(3) C(2) 169.9(2) . . . . yes O(4) C(18) C(3) C(4) -62.2(3) . . . . yes O(4) C(18) C(3) C(11) 72.3(3) . . . . yes C(1) C(2) C(3) C(4) 141.4(2) . . . . yes C(1) C(2) C(3) C(11) 20.7(2) . . . . yes C(1) C(2) C(3) C(18) -93.5(2) . . . . yes C(1) C(11) C(3) C(2) -20.3(2) . . . . yes C(1) C(11) C(3) C(4) -137.2(2) . . . . yes C(1) C(11) C(3) C(18) 92.8(2) . . . . yes C(1) C(11) C(10) C(5) 105.9(3) . . . . yes C(1) C(11) C(10) C(9) -73.6(3) . . . . yes C(1) C(12) C(13) C(14) -179.0(3) . . . . yes C(1) C(12) C(17) C(16) 180.0(3) . . . . yes C(2) C(1) C(11) C(3) 20.5(2) . . . . yes C(2) C(1) C(11) C(10) -92.8(2) . . . . yes C(2) C(1) C(12) C(13) -152.9(3) . . . . yes C(2) C(1) C(12) C(17) 27.8(4) . . . . yes C(2) C(3) C(11) C(10) 96.4(2) . . . . yes C(3) C(2) C(1) C(11) -20.6(2) . . . . yes C(3) C(2) C(1) C(12) -146.3(2) . . . . yes C(3) C(4) O(1) C(5) -10.1(3) . . . . yes C(3) C(11) C(1) C(12) 145.5(2) . . . . yes C(3) C(11) C(10) C(5) 7.7(3) . . . . yes C(3) C(11) C(10) C(9) -171.7(2) . . . . yes C(3) C(18) O(4) C(19) 177.5(3) . . . . yes C(4) O(1) C(5) C(6) 178.0(2) . . . . yes C(4) O(1) C(5) C(10) -3.6(4) . . . . yes C(4) C(3) C(11) C(10) -20.5(3) . . . . yes C(5) C(6) C(7) C(8) -0.5(5) . . . . yes C(5) C(10) C(9) C(8) -1.1(4) . . . . yes C(6) C(5) C(10) C(9) 2.1(4) . . . . yes C(6) C(5) C(10) C(11) -177.4(2) . . . . yes C(6) C(7) C(8) C(9) 1.5(5) . . . . yes C(7) C(6) C(5) C(10) -1.4(4) . . . . yes C(7) C(8) C(9) C(10) -0.7(4) . . . . yes C(8) C(9) C(10) C(11) 178.4(2) . . . . yes C(10) C(11) C(1) C(12) 32.2(3) . . . . yes C(10) C(11) C(3) C(18) -150.4(2) . . . . yes C(11) C(1) C(12) C(13) 98.8(3) . . . . yes C(11) C(1) C(12) C(17) -80.5(3) . . . . yes C(12) C(13) C(14) C(15) -0.5(5) . . . . yes C(12) C(17) C(16) C(15) -1.4(5) . . . . yes C(13) C(12) C(17) C(16) 0.7(5) . . . . yes C(13) C(14) C(15) C(16) -0.2(6) . . . . yes C(14) C(13) C(12) C(17) 0.3(5) . . . . yes C(14) C(15) C(16) C(17) 1.1(6) . . . . yes C(18) O(4) C(19) C(20) -162.8(5) . . . . yes C(18) O(4) C(19) C(20) -162.8(5) . . . . yes #------------------------------------------------------------------------------ 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 O(1) O(1) 3.301(4) . 3_666 ? O(1) C(4) 3.417(3) . 3_666 ? O(1) C(2) 3.540(3) . 3_666 ? O(1) O(2) 3.565(3) . 3_666 ? O(2) C(6) 3.371(4) . 3_666 ? O(2) C(14) 3.414(4) . 4_554 ? O(2) C(15) 3.479(4) . 4_554 ? O(2) C(5) 3.504(3) . 3_666 ? O(3) C(11) 3.326(3) . 2_656 ? O(3) C(13) 3.530(4) . 2_656 ? O(3) C(6) 3.555(4) . 4_555 ? O(4) C(7) 3.446(4) . 3_656 ? O(4) C(8) 3.549(3) . 3_656 ? C(5) C(9) 3.513(4) . 3_656 ?