# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Akikazu Matsumoto' _publ_contact_author_address ; Department of Applied Chemistry Osaka City Univesity 3-3-138 Sugimoto, Sumiyoshi-ku Osaka 558-8585 JAPAN ; _publ_contact_author_email MATSUMOTO@A-CHEM.ENG.OSAKA-CU.AC.JP _publ_section_title ; Direct observation of change in molecular structure of benzyl (Z,Z)-muconate during photoisomerization in the solid state ; loop_ _publ_author_name 'Akikazu Matsumoto' 'Daisuke Furukawa' 'Seiya Kobatake' data_ZZ-Bz _database_code_depnum_ccdc_archive 'CCDC 662879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibenzyl (Z,Z)-muconate ; _chemical_name_common 'Dibenzyl (Z,Z)-muconate' _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O4' _chemical_formula_sum 'C20 H18 O4' _chemical_formula_weight 322.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.332(4) _cell_length_b 5.682(2) _cell_length_c 14.791(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.86(4) _cell_angle_gamma 90.00 _cell_volume 835.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5942 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9824 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6512 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1877 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1877 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.44832(14) 0.1361(2) 0.12236(10) 0.0793(5) Uani 1 1 d . . . O2 O 0.29586(11) 0.32180(18) 0.17657(8) 0.0582(4) Uani 1 1 d . . . C1 C 0.46116(17) 0.5817(3) 0.01822(13) 0.0602(5) Uani 1 1 d . . . H1 H 0.4577 0.7355 -0.0038 0.072 Uiso 1 1 calc R . . C2 C 0.39317(18) 0.5357(3) 0.08070(13) 0.0631(5) Uani 1 1 d . . . H2 H 0.3458 0.6603 0.0971 0.076 Uiso 1 1 calc R . . C3 C 0.38520(15) 0.3100(3) 0.12621(11) 0.0509(4) Uani 1 1 d . . . C4 C 0.2804(2) 0.1127(3) 0.22763(13) 0.0651(5) Uani 1 1 d . . . H3 H 0.3680 0.0481 0.2590 0.078 Uiso 1 1 calc R . . H4 H 0.2303 -0.0050 0.1845 0.078 Uiso 1 1 calc R . . C5 C 0.20701(15) 0.1734(2) 0.29840(11) 0.0487(4) Uani 1 1 d . . . C6 C 0.23699(17) 0.3737(3) 0.35285(12) 0.0572(4) Uani 1 1 d . . . H5 H 0.3026 0.4771 0.3445 0.069 Uiso 1 1 calc R . . C7 C 0.16998(19) 0.4206(3) 0.41936(12) 0.0642(5) Uani 1 1 d . . . H6 H 0.1898 0.5565 0.4555 0.077 Uiso 1 1 calc R . . C8 C 0.07415(18) 0.2680(3) 0.43257(12) 0.0652(5) Uani 1 1 d . . . H7 H 0.0298 0.2994 0.4781 0.078 Uiso 1 1 calc R . . C9 C 0.04395(18) 0.0702(3) 0.37892(13) 0.0651(5) Uani 1 1 d . . . H8 H -0.0213 -0.0332 0.3878 0.078 Uiso 1 1 calc R . . C10 C 0.10951(17) 0.0226(3) 0.31165(11) 0.0570(4) Uani 1 1 d . . . H9 H 0.0879 -0.1121 0.2749 0.068 Uiso 1 1 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 0.0942(9) 0.0628(8) 0.1059(11) 0.0221(7) 0.0694(9) 0.0273(7) O2 0.0668(7) 0.0595(7) 0.0616(7) 0.0139(5) 0.0401(6) 0.0151(5) C1 0.0742(11) 0.0477(8) 0.0725(11) 0.0084(8) 0.0431(9) 0.0085(8) C2 0.0776(11) 0.0525(10) 0.0751(12) 0.0080(8) 0.0477(10) 0.0150(9) C3 0.0497(8) 0.0548(9) 0.0553(9) 0.0023(7) 0.0263(7) 0.0067(8) C4 0.0849(12) 0.0563(9) 0.0677(11) 0.0112(8) 0.0440(10) 0.0104(9) C5 0.0540(8) 0.0489(8) 0.0482(9) 0.0066(7) 0.0227(7) 0.0054(7) C6 0.0608(10) 0.0551(9) 0.0622(10) -0.0015(8) 0.0279(8) -0.0100(8) C7 0.0823(12) 0.0591(10) 0.0570(11) -0.0080(8) 0.0289(9) -0.0026(9) C8 0.0794(12) 0.0711(11) 0.0569(11) 0.0074(9) 0.0387(10) 0.0067(10) C9 0.0687(10) 0.0685(11) 0.0667(12) 0.0134(9) 0.0333(9) -0.0115(9) C10 0.0711(10) 0.0513(9) 0.0519(9) 0.0013(7) 0.0225(8) -0.0096(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.1941(18) . ? O2 C3 1.3368(18) . ? O2 C4 1.4402(18) . ? C1 C2 1.331(2) . ? C1 C1 1.426(3) 3_665 ? C2 C3 1.461(2) . ? C4 C5 1.491(2) . ? C5 C10 1.376(2) . ? C5 C6 1.380(2) . ? C6 C7 1.375(2) . ? C7 C8 1.370(3) . ? C8 C9 1.362(3) . ? C9 C10 1.375(2) . ? 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_3 _geom_angle_publ_flag C3 O2 C4 116.33(12) . . ? C2 C1 C1 126.36(19) . 3_665 ? C1 C2 C3 126.83(15) . . ? O1 C3 O2 122.50(14) . . ? O1 C3 C2 127.17(15) . . ? O2 C3 C2 110.32(12) . . ? O2 C4 C5 109.16(13) . . ? C10 C5 C6 119.11(14) . . ? C10 C5 C4 119.23(15) . . ? C6 C5 C4 121.63(14) . . ? C7 C6 C5 120.04(15) . . ? C8 C7 C6 120.29(17) . . ? C9 C8 C7 119.92(16) . . ? C8 C9 C10 120.27(16) . . ? C9 C10 C5 120.36(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 1.0(4) 3_665 . . . ? C4 O2 C3 O1 0.8(3) . . . . ? C4 O2 C3 C2 -178.31(14) . . . . ? C1 C2 C3 O1 8.1(3) . . . . ? C1 C2 C3 O2 -172.93(19) . . . . ? C3 O2 C4 C5 165.10(14) . . . . ? O2 C4 C5 C10 138.61(16) . . . . ? O2 C4 C5 C6 -43.2(2) . . . . ? C10 C5 C6 C7 0.1(2) . . . . ? C4 C5 C6 C7 -178.09(16) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C5 0.5(3) . . . . ? C6 C5 C10 C9 -0.7(2) . . . . ? C4 C5 C10 C9 177.57(15) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.149 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.066 data_ZZ-Bz-2 _database_code_depnum_ccdc_archive 'CCDC 662880' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibenzyl (Z,Z)-muconate (64.7%) + dibenzyl (E,E)-muconate (35.3%) ; _chemical_name_common ;Dibenzyl (Z,Z)-muconate (64.7%) + dibenzyl (E,E)-muconate (35.3%) ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O4' _chemical_formula_sum 'C20 H18 O4' _chemical_formula_weight 322.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.328(6) _cell_length_b 5.765(4) _cell_length_c 15.005(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.00(3) _cell_angle_gamma 90.00 _cell_volume 858.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3837 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 24.8 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; The crystal was employed after irradiation with UV light for 27 h at room temperature. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6993 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.30 _reflns_number_total 1933 _reflns_number_gt 842 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material CrystalStructure _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. The bond length and geometry of phenyl groups were restrained using SAME and FLAT because of disordered atoms of (ZZ) and (EE)-isomers. ; _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^)+(0.1303P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1933 _refine_ls_number_parameters 203 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1564 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2290 _refine_ls_wR_factor_gt 0.1892 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1Z O 0.4485(7) 0.1291(13) 0.1199(4) 0.101(2) Uani 0.647(15) 1 d P A 1 O2Z O 0.2962(8) 0.3072(19) 0.1775(5) 0.074(2) Uani 0.647(15) 1 d P A 1 C1Z C 0.4593(6) 0.5803(16) 0.0169(5) 0.086(2) Uani 0.647(15) 1 d P . 1 H1Z H 0.4543 0.7320 -0.0048 0.103 Uiso 0.647(15) 1 calc PR A 1 C2Z C 0.3897(6) 0.5271(15) 0.0774(4) 0.085(2) Uani 0.647(15) 1 d P A 1 H2Z H 0.3388 0.6469 0.0920 0.102 Uiso 0.647(15) 1 calc PR A 1 C3Z C 0.3829(5) 0.2960(16) 0.1256(4) 0.0662(19) Uani 0.647(15) 1 d P A 1 C4Z C 0.2801(10) 0.1036(18) 0.2300(6) 0.086(3) Uani 0.647(15) 1 d P A 1 H4Z1 H 0.3672 0.0391 0.2620 0.103 Uiso 0.647(15) 1 calc PR A 1 H4Z2 H 0.2283 -0.0141 0.1891 0.103 Uiso 0.647(15) 1 calc PR A 1 C5Z C 0.2080(11) 0.181(2) 0.2975(8) 0.065(3) Uani 0.647(15) 1 d PD A 1 C6Z C 0.2342(9) 0.376(2) 0.3507(8) 0.067(3) Uani 0.647(15) 1 d PD A 1 H6Z H 0.2996 0.4803 0.3440 0.080 Uiso 0.647(15) 1 calc PRD A 1 C7Z C 0.1620(13) 0.4181(14) 0.4154(8) 0.107(6) Uani 0.647(15) 1 d PD A 1 H7Z H 0.1776 0.5522 0.4512 0.129 Uiso 0.647(15) 1 calc PRD A 1 C8Z C 0.0686(10) 0.2612(19) 0.4254(8) 0.091(5) Uani 0.647(15) 1 d PD A 1 H8Z H 0.0209 0.2910 0.4684 0.109 Uiso 0.647(15) 1 calc PRD A 1 C9Z C 0.0429(10) 0.065(2) 0.3755(8) 0.079(3) Uani 0.647(15) 1 d PD A 1 H9Z H -0.0195 -0.0424 0.3848 0.095 Uiso 0.647(15) 1 calc PRD A 1 C10Z C 0.1131(9) 0.0253(16) 0.3087(5) 0.088(3) Uani 0.647(15) 1 d PD A 1 H10Z H 0.0951 -0.1071 0.2720 0.106 Uiso 0.647(15) 1 calc PRD A 1 O1E O 0.4269(15) 0.010(3) 0.1316(11) 0.142(5) Uani 0.353(15) 1 d P A 2 O2E O 0.302(2) 0.269(5) 0.1827(15) 0.147(9) Uani 0.353(15) 1 d P A 2 C1E C 0.4827(14) 0.407(4) 0.0263(8) 0.099(6) Uani 0.353(15) 1 d P . 2 H1E H 0.5172 0.2628 0.0163 0.119 Uiso 0.353(15) 1 calc PR A 2 C2E C 0.4095(15) 0.405(3) 0.0870(10) 0.090(4) Uiso 0.353(15) 1 d P A 2 H2E H 0.3724 0.5424 0.1009 0.108 Uiso 0.353(15) 1 calc PR A 2 C3E C 0.386(3) 0.188(5) 0.1322(16) 0.129(10) Uiso 0.353(15) 1 d P A 2 C4E C 0.274(2) 0.061(5) 0.2334(17) 0.152(12) Uani 0.353(15) 1 d P A 2 H4E1 H 0.3587 -0.0149 0.2643 0.183 Uiso 0.353(15) 1 calc PR A 2 H4E2 H 0.2199 -0.0481 0.1895 0.183 Uiso 0.353(15) 1 calc PR A 2 C5E C 0.199(2) 0.128(4) 0.3067(16) 0.074(7) Uani 0.353(15) 1 d PD A 2 C6E C 0.238(2) 0.329(4) 0.3529(15) 0.111(11) Uani 0.353(15) 1 d PD A 2 H6E H 0.3085 0.4130 0.3411 0.133 Uiso 0.353(15) 1 calc PRD A 2 C7E C 0.1760(15) 0.416(3) 0.4176(9) 0.073(6) Uani 0.353(15) 1 d PD A 2 H7E H 0.2004 0.5582 0.4462 0.087 Uiso 0.353(15) 1 calc PRD A 2 C8E C 0.078(2) 0.283(3) 0.4374(15) 0.110(11) Uani 0.353(15) 1 d PD A 2 H8E H 0.0424 0.3286 0.4852 0.132 Uiso 0.353(15) 1 calc PRD A 2 C9E C 0.031(2) 0.088(3) 0.3903(17) 0.123(10) Uani 0.353(15) 1 d PD A 2 H9E H -0.0415 0.0096 0.4010 0.148 Uiso 0.353(15) 1 calc PRD A 2 C10E C 0.0939(15) 0.005(3) 0.3243(11) 0.060(4) Uiso 0.353(15) 1 d PD A 2 H10E H 0.0645 -0.1319 0.2926 0.072 Uiso 0.353(15) 1 calc PRD A 2 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 O1Z 0.106(3) 0.088(4) 0.135(3) 0.024(3) 0.077(3) 0.030(3) O2Z 0.073(4) 0.088(4) 0.067(3) 0.010(3) 0.032(3) 0.020(3) C1Z 0.096(4) 0.072(4) 0.101(4) 0.012(3) 0.046(4) 0.025(3) C2Z 0.098(4) 0.082(5) 0.097(4) 0.017(3) 0.065(3) 0.014(3) C3Z 0.056(3) 0.082(5) 0.069(3) 0.001(3) 0.030(2) 0.010(3) C4Z 0.116(6) 0.068(4) 0.100(6) 0.011(3) 0.073(5) 0.032(4) C5Z 0.075(4) 0.061(6) 0.062(4) 0.020(4) 0.026(4) 0.003(4) C6Z 0.067(5) 0.048(3) 0.089(7) 0.003(3) 0.028(4) -0.004(3) C7Z 0.151(11) 0.057(6) 0.127(10) -0.011(5) 0.060(8) 0.024(6) C8Z 0.085(5) 0.113(11) 0.096(7) 0.021(6) 0.062(5) -0.004(6) C9Z 0.075(4) 0.084(6) 0.084(5) 0.003(4) 0.033(4) -0.004(4) C10Z 0.113(6) 0.084(4) 0.082(4) 0.020(3) 0.051(4) -0.017(3) O1E 0.187(10) 0.099(9) 0.183(10) 0.001(8) 0.123(8) 0.021(8) O2E 0.142(14) 0.148(17) 0.200(18) -0.031(13) 0.130(13) 0.008(11) C1E 0.100(8) 0.132(16) 0.090(7) -0.021(8) 0.066(7) -0.010(8) C4E 0.106(13) 0.18(2) 0.123(16) 0.023(14) -0.042(11) -0.029(12) C5E 0.108(11) 0.037(8) 0.097(12) 0.008(7) 0.060(9) 0.002(6) C6E 0.137(19) 0.102(17) 0.114(17) -0.016(13) 0.070(14) -0.026(12) C7E 0.061(7) 0.114(15) 0.045(8) 0.004(7) 0.016(6) -0.035(7) C8E 0.20(2) 0.055(10) 0.068(9) -0.014(8) 0.017(10) 0.032(12) C9E 0.17(2) 0.063(11) 0.15(2) 0.024(11) 0.075(14) -0.025(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1Z C3Z 1.193(10) . ? O2Z C3Z 1.340(10) . ? O2Z C4Z 1.448(15) . ? C1Z C2Z 1.340(10) . ? C1Z C1Z 1.434(17) 3_665 ? C2Z C3Z 1.527(10) . ? C4Z C5Z 1.481(14) . ? C5Z C6Z 1.363(9) . ? C5Z C10Z 1.373(9) . ? C6Z C7Z 1.399(9) . ? C7Z C8Z 1.360(9) . ? C8Z C9Z 1.344(10) . ? C9Z C10Z 1.407(9) . ? O1E C3E 1.11(3) . ? O2E C3E 1.38(3) . ? O2E C4E 1.49(4) . ? C1E C2E 1.34(2) . ? C1E C1E 1.44(4) 3_665 ? C2E C3E 1.47(2) . ? C4E C5E 1.56(3) . ? C5E C6E 1.355(14) . ? C5E C10E 1.383(14) . ? C6E C7E 1.393(15) . ? C7E C8E 1.365(15) . ? C8E C9E 1.342(15) . ? C9E C10E 1.407(14) . ? 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_3 _geom_angle_publ_flag C3Z O2Z C4Z 118.2(8) . . ? C2Z C1Z C1Z 124.6(10) . 3_665 ? C1Z C2Z C3Z 128.6(6) . . ? O1Z C3Z O2Z 124.3(8) . . ? O1Z C3Z C2Z 124.6(5) . . ? O2Z C3Z C2Z 111.0(6) . . ? O2Z C4Z C5Z 106.4(8) . . ? C6Z C5Z C10Z 120.0(9) . . ? C6Z C5Z C4Z 126.3(10) . . ? C10Z C5Z C4Z 113.5(9) . . ? C5Z C6Z C7Z 119.5(8) . . ? C8Z C7Z C6Z 119.4(7) . . ? C9Z C8Z C7Z 122.4(7) . . ? C8Z C9Z C10Z 118.1(8) . . ? C5Z C10Z C9Z 120.5(8) . . ? C3E O2E C4E 104(2) . . ? C2E C1E C1E 131(2) . 3_665 ? C1E C2E C3E 121.1(17) . . ? O1E C3E O2E 128(2) . . ? O1E C3E C2E 132(2) . . ? O2E C3E C2E 100(2) . . ? O2E C4E C5E 111(2) . . ? C6E C5E C10E 118.6(15) . . ? C6E C5E C4E 116.1(17) . . ? C10E C5E C4E 125.2(17) . . ? C5E C6E C7E 122.2(16) . . ? C8E C7E C6E 117.6(14) . . ? C9E C8E C7E 122.2(16) . . ? C8E C9E C10E 119.2(15) . . ? C5E C10E C9E 119.8(13) . . ? 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 C1Z C1Z C2Z C3Z 1.9(12) 3_665 . . . ? C4Z O2Z C3Z O1Z -0.3(11) . . . . ? C4Z O2Z C3Z C2Z -178.5(7) . . . . ? C1Z C2Z C3Z O1Z 5.3(10) . . . . ? C1Z C2Z C3Z O2Z -176.5(7) . . . . ? C3Z O2Z C4Z C5Z 166.0(8) . . . . ? O2Z C4Z C5Z C6Z -44.4(11) . . . . ? O2Z C4Z C5Z C10Z 140.3(9) . . . . ? C10Z C5Z C6Z C7Z -1.2(9) . . . . ? C4Z C5Z C6Z C7Z -176.2(11) . . . . ? C5Z C6Z C7Z C8Z 1.3(9) . . . . ? C6Z C7Z C8Z C9Z 0.3(15) . . . . ? C7Z C8Z C9Z C10Z -1.9(17) . . . . ? C6Z C5Z C10Z C9Z -0.5(13) . . . . ? C4Z C5Z C10Z C9Z 175.2(10) . . . . ? C8Z C9Z C10Z C5Z 2.0(16) . . . . ? C1E C1E C2E C3E 179.4(17) 3_665 . . . ? C4E O2E C3E O1E -2(4) . . . . ? C4E O2E C3E C2E -178.9(17) . . . . ? C1E C2E C3E O1E 6(4) . . . . ? C1E C2E C3E O2E -176.9(15) . . . . ? C3E O2E C4E C5E 170.8(18) . . . . ? O2E C4E C5E C6E -38(2) . . . . ? O2E C4E C5E C10E 139(2) . . . . ? C10E C5E C6E C7E 0.3(13) . . . . ? C4E C5E C6E C7E 177(2) . . . . ? C5E C6E C7E C8E 3.7(13) . . . . ? C6E C7E C8E C9E -7(3) . . . . ? C7E C8E C9E C10E 6(3) . . . . ? C6E C5E C10E C9E -1(2) . . . . ? C4E C5E C10E C9E -178(2) . . . . ? C8E C9E C10E C5E -2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.178 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.049 data_EE-Bz _database_code_depnum_ccdc_archive 'CCDC 662881' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibenzyl (E,E)-muconate ; _chemical_name_common 'Dibenzyl (E,E)-muconate' _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O4' _chemical_formula_sum 'C20 H18 O4' _chemical_formula_weight 322.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.167(3) _cell_length_b 5.7038(11) _cell_length_c 17.002(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.803(4) _cell_angle_gamma 90.00 _cell_volume 859.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2905 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 24.6 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8154 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3569 _reflns_number_gt 1625 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.4(14) _refine_ls_number_reflns 3569 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1292 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 0.799 _refine_ls_restrained_S_all 0.799 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.4559(2) 0.4652(4) 0.84919(13) 0.0786(7) Uani 1 1 d . . . O2 O 0.35892(19) 0.7291(4) 0.91986(11) 0.0620(5) Uani 1 1 d . . . O3 O 0.6151(3) 1.4452(4) 0.61828(13) 0.0880(8) Uani 1 1 d . . . O4 O 0.7167(2) 1.1956(3) 0.54616(11) 0.0635(5) Uani 1 1 d . . . C1 C 0.5179(3) 0.8526(5) 0.75306(17) 0.0525(7) Uani 1 1 d . . . H1 H 0.5413 0.7036 0.7378 0.063 Uiso 1 1 calc R . . C2 C 0.4576(3) 0.8700(5) 0.81597(17) 0.0537(7) Uani 1 1 d . . . H2 H 0.4336 1.0181 0.8318 0.064 Uiso 1 1 calc R . . C3 C 0.4272(3) 0.6654(5) 0.86159(16) 0.0534(7) Uani 1 1 d . . . C4 C 0.3087(3) 0.5467(5) 0.96590(17) 0.0680(9) Uani 1 1 d . . . H3 H 0.3177 0.6006 1.0210 0.082 Uiso 1 1 calc R . . H4 H 0.3723 0.4094 0.9685 0.082 Uiso 1 1 calc R . . C5 C 0.1475(3) 0.4826(4) 0.92683(15) 0.0487(7) Uani 1 1 d . . . C6 C 0.1098(4) 0.2726(5) 0.88509(18) 0.0691(9) Uani 1 1 d . . . H5 H 0.1845 0.1658 0.8816 0.083 Uiso 1 1 calc R . . C7 C -0.0409(4) 0.2243(6) 0.84871(18) 0.0743(9) Uani 1 1 d . . . H6 H -0.0665 0.0836 0.8210 0.089 Uiso 1 1 calc R . . C8 C -0.1523(4) 0.3793(6) 0.85282(19) 0.0731(9) Uani 1 1 d . . . H7 H -0.2526 0.3459 0.8275 0.088 Uiso 1 1 calc R . . C9 C -0.1142(4) 0.5840(5) 0.89459(19) 0.0714(9) Uani 1 1 d . . . H8 H -0.1893 0.6896 0.8985 0.086 Uiso 1 1 calc R . . C10 C 0.0328(3) 0.6348(4) 0.93057(15) 0.0545(7) Uani 1 1 d . . . H9 H 0.0564 0.7758 0.9584 0.065 Uiso 1 1 calc R . . C11 C 0.5494(3) 1.0493(5) 0.70701(16) 0.0533(7) Uani 1 1 d . . . H10 H 0.5217 1.1970 0.7213 0.064 Uiso 1 1 calc R . . C12 C 0.6145(3) 1.0374(5) 0.64600(17) 0.0564(8) Uani 1 1 d . . . H11 H 0.6412 0.8917 0.6295 0.068 Uiso 1 1 calc R . . C13 C 0.6456(3) 1.2488(5) 0.60382(17) 0.0576(8) Uani 1 1 d . . . C14 C 0.7543(3) 1.3896(5) 0.50031(18) 0.0646(8) Uani 1 1 d . . . H12 H 0.8283 1.4894 0.5359 0.078 Uiso 1 1 calc R . . H13 H 0.6647 1.4826 0.4778 0.078 Uiso 1 1 calc R . . C15 C 0.8167(3) 1.2989(4) 0.43289(16) 0.0514(7) Uani 1 1 d . . . C16 C 0.9186(3) 1.4330(5) 0.40653(18) 0.0708(9) Uani 1 1 d . . . H14 H 0.9516 1.5740 0.4326 0.085 Uiso 1 1 calc R . . C17 C 0.9733(4) 1.3616(7) 0.3415(2) 0.0871(11) Uani 1 1 d . . . H15 H 1.0414 1.4563 0.3240 0.104 Uiso 1 1 calc R . . C18 C 0.9289(4) 1.1555(7) 0.3033(2) 0.0792(10) Uani 1 1 d . . . H16 H 0.9656 1.1081 0.2596 0.095 Uiso 1 1 calc R . . C19 C 0.8287(4) 1.0179(5) 0.33018(18) 0.0720(9) Uani 1 1 d . . . H17 H 0.7990 0.8745 0.3052 0.086 Uiso 1 1 calc R . . C20 C 0.7714(3) 1.0902(5) 0.39415(17) 0.0640(8) Uani 1 1 d . . . H18 H 0.7018 0.9967 0.4109 0.077 Uiso 1 1 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 0.0986(17) 0.0585(13) 0.0920(17) 0.0096(11) 0.0486(14) 0.0142(11) O2 0.0604(13) 0.0735(13) 0.0594(13) 0.0004(11) 0.0289(11) -0.0005(11) O3 0.128(2) 0.0532(14) 0.1085(19) 0.0000(13) 0.0776(17) 0.0069(13) O4 0.0887(14) 0.0534(12) 0.0605(13) 0.0075(10) 0.0410(12) 0.0109(10) C1 0.0513(18) 0.0520(16) 0.0564(18) -0.0051(14) 0.0181(16) 0.0007(13) C2 0.0547(18) 0.0516(17) 0.060(2) -0.0038(15) 0.0234(17) -0.0048(14) C3 0.0427(17) 0.067(2) 0.053(2) -0.0032(17) 0.0172(15) -0.0003(15) C4 0.063(2) 0.092(2) 0.055(2) 0.0236(18) 0.0257(17) 0.0061(17) C5 0.0541(18) 0.0512(16) 0.0441(17) 0.0050(13) 0.0186(14) 0.0037(14) C6 0.095(3) 0.0583(19) 0.066(2) 0.0097(16) 0.041(2) 0.0140(18) C7 0.103(3) 0.060(2) 0.061(2) -0.0090(17) 0.023(2) -0.017(2) C8 0.066(2) 0.086(2) 0.067(2) 0.001(2) 0.0142(18) -0.008(2) C9 0.065(2) 0.071(2) 0.080(2) -0.0016(18) 0.0219(19) 0.0074(18) C10 0.060(2) 0.0518(17) 0.0534(19) -0.0046(13) 0.0182(15) 0.0000(15) C11 0.0524(18) 0.0508(17) 0.0589(18) -0.0027(14) 0.0182(15) -0.0049(13) C12 0.064(2) 0.0522(18) 0.059(2) -0.0027(15) 0.0262(17) 0.0036(14) C13 0.0613(19) 0.0563(19) 0.059(2) 0.0052(17) 0.0226(17) 0.0050(16) C14 0.087(2) 0.0559(18) 0.056(2) 0.0104(16) 0.0285(18) 0.0049(16) C15 0.0570(19) 0.0532(19) 0.0425(18) 0.0054(14) 0.0100(15) 0.0032(14) C16 0.085(2) 0.067(2) 0.059(2) -0.0008(16) 0.0154(19) -0.0152(18) C17 0.090(3) 0.116(3) 0.067(2) -0.006(2) 0.040(2) -0.031(2) C18 0.087(3) 0.099(3) 0.058(2) -0.007(2) 0.030(2) 0.006(2) C19 0.091(3) 0.064(2) 0.058(2) -0.0094(16) 0.0140(19) -0.0005(18) C20 0.075(2) 0.063(2) 0.056(2) 0.0014(16) 0.0202(17) -0.0075(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.202(3) . ? O2 C3 1.350(3) . ? O2 C4 1.446(3) . ? O3 C13 1.195(3) . ? O4 C13 1.343(3) . ? O4 C14 1.445(3) . ? C1 C2 1.327(3) . ? C1 C11 1.439(3) . ? C2 C3 1.467(4) . ? C4 C5 1.502(4) . ? C5 C10 1.377(3) . ? C5 C6 1.390(4) . ? C6 C7 1.390(4) . ? C7 C8 1.366(4) . ? C8 C9 1.365(4) . ? C9 C10 1.361(3) . ? C11 C12 1.324(3) . ? C12 C13 1.467(4) . ? C14 C15 1.499(3) . ? C15 C16 1.368(3) . ? C15 C20 1.373(3) . ? C16 C17 1.386(4) . ? C17 C18 1.355(5) . ? C18 C19 1.372(4) . ? C19 C20 1.386(4) . ? 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_3 _geom_angle_publ_flag C3 O2 C4 118.4(2) . . ? C13 O4 C14 116.6(2) . . ? C2 C1 C11 124.3(3) . . ? C1 C2 C3 122.8(3) . . ? O1 C3 O2 123.2(3) . . ? O1 C3 C2 125.7(2) . . ? O2 C3 C2 111.1(3) . . ? O2 C4 C5 110.4(2) . . ? C10 C5 C6 118.2(3) . . ? C10 C5 C4 120.2(3) . . ? C6 C5 C4 121.6(3) . . ? C7 C6 C5 119.2(3) . . ? C8 C7 C6 121.3(3) . . ? C9 C8 C7 119.0(3) . . ? C10 C9 C8 120.6(3) . . ? C9 C10 C5 121.7(3) . . ? C12 C11 C1 125.4(2) . . ? C11 C12 C13 121.6(3) . . ? O3 C13 O4 122.9(3) . . ? O3 C13 C12 125.8(3) . . ? O4 C13 C12 111.2(3) . . ? O4 C14 C15 109.8(2) . . ? C16 C15 C20 118.4(3) . . ? C16 C15 C14 118.9(3) . . ? C20 C15 C14 122.6(3) . . ? C15 C16 C17 120.9(3) . . ? C18 C17 C16 120.8(3) . . ? C17 C18 C19 118.7(3) . . ? C18 C19 C20 120.8(3) . . ? C15 C20 C19 120.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 -179.9(2) . . . . ? C4 O2 C3 O1 -4.3(4) . . . . ? C4 O2 C3 C2 174.6(2) . . . . ? C1 C2 C3 O1 2.0(4) . . . . ? C1 C2 C3 O2 -176.9(2) . . . . ? C3 O2 C4 C5 -92.3(3) . . . . ? O2 C4 C5 C10 -71.9(3) . . . . ? O2 C4 C5 C6 107.0(3) . . . . ? C10 C5 C6 C7 0.2(4) . . . . ? C4 C5 C6 C7 -178.7(2) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C7 C8 C9 C10 1.0(5) . . . . ? C8 C9 C10 C5 -0.5(4) . . . . ? C6 C5 C10 C9 -0.1(4) . . . . ? C4 C5 C10 C9 178.8(2) . . . . ? C2 C1 C11 C12 177.4(3) . . . . ? C1 C11 C12 C13 -178.5(2) . . . . ? C14 O4 C13 O3 -0.8(4) . . . . ? C14 O4 C13 C12 -179.8(2) . . . . ? C11 C12 C13 O3 -1.1(5) . . . . ? C11 C12 C13 O4 177.8(3) . . . . ? C13 O4 C14 C15 -173.7(2) . . . . ? O4 C14 C15 C16 -150.6(2) . . . . ? O4 C14 C15 C20 32.0(4) . . . . ? C20 C15 C16 C17 0.8(4) . . . . ? C14 C15 C16 C17 -176.6(3) . . . . ? C15 C16 C17 C18 -1.0(5) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 1.4(5) . . . . ? C16 C15 C20 C19 0.4(4) . . . . ? C14 C15 C20 C19 177.7(3) . . . . ? C18 C19 C20 C15 -1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.098 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.027