# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Pi-Tai Chou' _publ_contact_author_address ; Department of Chemistry National Taiwan University No 1 sec 4 Rosevolt Rd. Taipei 106 TAIWAN ; _publ_contact_author_email CHOP@NTU.EDU.TW _publ_section_title ; A New Class of Laser Dyes, 2-Oxa-bicyclo[3.3.0]octa-4,8-diene-3,6-diones, with Unity Fluorescence Yield ; loop_ _publ_author_name 'Pi-Tai Chou.' 'Elise Y. Li' 'Yi-Hong Liu.' 'Shiuh-Tzung Liu.' ; Shiuh-Ming Peng ; 'Chao-Yu Wang.' 'Yu-Shan Yeh.' data_ic11005 _database_code_depnum_ccdc_archive 'CCDC 602233' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H12 O3' _chemical_formula_weight 288.29 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.7937(4) _cell_length_b 12.9224(5) _cell_length_c 18.4121(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2806.06(17) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 22828 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description prismatic _exptl_crystal_colour pale _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12826 _diffrn_reflns_av_R_equivalents 0.1298 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2533 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1065P)^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 SHELXL _refine_ls_extinction_coef 0.181(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2533 _refine_ls_number_parameters 398 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1411 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.002 _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 0.1408(4) 0.6267(3) 0.4442(2) 0.0601(11) Uani 1 1 d . . . O2 O 0.0078(4) 0.7194(3) 0.5016(3) 0.0807(13) Uani 1 1 d . . . O3 O 0.0782(5) 0.2781(4) 0.4962(3) 0.0943(15) Uani 1 1 d . . . C1 C 0.0461(5) 0.6346(5) 0.4896(3) 0.0637(15) Uani 1 1 d . . . C2 C 0.0091(6) 0.5289(6) 0.5124(3) 0.0574(15) Uani 1 1 d . . . C3 C 0.0861(5) 0.4647(5) 0.4795(3) 0.0571(14) Uani 1 1 d . . . C4 C 0.1193(6) 0.3548(5) 0.4694(4) 0.0647(18) Uani 1 1 d . . . C5 C 0.2217(5) 0.3556(4) 0.4198(3) 0.0655(16) Uani 1 1 d . . . H5A H 0.2060 0.3175 0.3755 0.079 Uiso 1 1 calc R . . H5B H 0.2865 0.3242 0.4437 0.079 Uiso 1 1 calc R . . C6 C 0.2456(5) 0.4699(5) 0.4026(3) 0.0566(14) Uani 1 1 d . . . C7 C 0.1644(6) 0.5220(5) 0.4389(4) 0.0534(15) Uani 1 1 d . . . C8 C 0.3379(7) 0.5049(4) 0.3570(4) 0.059(2) Uani 1 1 d . . . C9 C 0.3579(5) 0.6093(5) 0.3451(3) 0.0652(16) Uani 1 1 d . . . H9A H 0.3082 0.6584 0.3639 0.078 Uiso 1 1 calc R . . C10 C 0.4508(5) 0.6406(5) 0.3056(4) 0.0753(17) Uani 1 1 d . . . H10A H 0.4640 0.7108 0.2983 0.090 Uiso 1 1 calc R . . C11 C 0.5245(7) 0.5684(7) 0.2767(4) 0.077(2) Uani 1 1 d . . . H11A H 0.5874 0.5904 0.2504 0.093 Uiso 1 1 calc R . . C12 C 0.5057(7) 0.4642(7) 0.2866(4) 0.076(2) Uani 1 1 d . . . H12A H 0.5550 0.4155 0.2670 0.091 Uiso 1 1 calc R . . C13 C 0.4119(6) 0.4334(5) 0.3263(4) 0.0715(17) Uani 1 1 d . . . H13A H 0.3980 0.3631 0.3325 0.086 Uiso 1 1 calc R . . C14 C -0.0879(8) 0.5091(6) 0.5596(4) 0.066(2) Uani 1 1 d . . . C15 C -0.1180(7) 0.4065(7) 0.5743(4) 0.081(2) Uani 1 1 d . . . H15A H -0.0761 0.3528 0.5541 0.098 Uiso 1 1 calc R . . C16 C -0.2093(7) 0.3841(7) 0.6186(5) 0.102(3) Uani 1 1 d . . . H16A H -0.2285 0.3158 0.6288 0.123 Uiso 1 1 calc R . . C17 C -0.2713(7) 0.4644(8) 0.6476(5) 0.096(3) Uani 1 1 d . . . H17A H -0.3333 0.4494 0.6769 0.116 Uiso 1 1 calc R . . C18 C -0.2447(8) 0.5648(7) 0.6345(5) 0.094(3) Uani 1 1 d . . . H18A H -0.2880 0.6175 0.6548 0.112 Uiso 1 1 calc R . . C19 C -0.1519(6) 0.5888(7) 0.5903(4) 0.075(2) Uani 1 1 d . . . H19A H -0.1329 0.6575 0.5814 0.091 Uiso 1 1 calc R . . O4 O 0.1064(3) 0.1246(3) 0.3134(3) 0.0598(11) Uani 1 1 d . . . O5 O 0.2398(5) 0.2174(4) 0.2549(3) 0.0830(14) Uani 1 1 d . . . O6 O 0.1743(5) -0.2244(4) 0.2629(3) 0.0929(15) Uani 1 1 d . . . C20 C 0.2016(5) 0.1330(5) 0.2678(3) 0.0606(15) Uani 1 1 d . . . C21 C 0.2378(6) 0.0277(6) 0.2453(3) 0.0591(15) Uani 1 1 d . . . C22 C 0.1630(5) -0.0373(5) 0.2782(3) 0.0560(14) Uani 1 1 d . . . C23 C 0.1285(6) -0.1468(5) 0.2876(4) 0.0669(19) Uani 1 1 d . . . C24 C 0.0270(5) -0.1469(4) 0.3365(3) 0.0662(16) Uani 1 1 d . . . H24A H 0.0424 -0.1855 0.3806 0.079 Uiso 1 1 calc R . . H24B H -0.0378 -0.1777 0.3123 0.079 Uiso 1 1 calc R . . C25 C 0.0045(5) -0.0342(5) 0.3537(3) 0.0544(13) Uani 1 1 d . . . C26 C 0.0838(6) 0.0205(5) 0.3192(4) 0.0553(16) Uani 1 1 d . . . C27 C -0.0884(7) 0.0007(4) 0.3993(5) 0.054(2) Uani 1 1 d . . . C28 C -0.1674(5) -0.0704(5) 0.4273(3) 0.0668(16) Uani 1 1 d . . . H28A H -0.1589 -0.1405 0.4173 0.080 Uiso 1 1 calc R . . C29 C -0.2567(7) -0.0381(7) 0.4691(4) 0.077(2) Uani 1 1 d . . . H29A H -0.3076 -0.0867 0.4872 0.093 Uiso 1 1 calc R . . C30 C -0.2722(7) 0.0648(6) 0.4848(4) 0.081(2) Uani 1 1 d . . . H30A H -0.3345 0.0865 0.5118 0.097 Uiso 1 1 calc R . . C31 C -0.1935(5) 0.1357(5) 0.4596(4) 0.0769(18) Uani 1 1 d . . . H31A H -0.2016 0.2053 0.4713 0.092 Uiso 1 1 calc R . . C32 C -0.1042(5) 0.1051(5) 0.4178(3) 0.0660(16) Uani 1 1 d . . . H32A H -0.0528 0.1543 0.4012 0.079 Uiso 1 1 calc R . . C33 C 0.3344(7) 0.0075(5) 0.1981(4) 0.061(2) Uani 1 1 d . . . C34 C 0.3902(6) 0.0867(7) 0.1602(4) 0.078(2) Uani 1 1 d . . . H34A H 0.3642 0.1544 0.1639 0.093 Uiso 1 1 calc R . . C35 C 0.4819(7) 0.0653(8) 0.1181(5) 0.098(3) Uani 1 1 d . . . H35A H 0.5178 0.1190 0.0935 0.117 Uiso 1 1 calc R . . C36 C 0.5234(7) -0.0348(10) 0.1108(5) 0.107(3) Uani 1 1 d . . . H36A H 0.5861 -0.0487 0.0818 0.129 Uiso 1 1 calc R . . C37 C 0.4696(6) -0.1119(7) 0.1473(4) 0.090(2) Uani 1 1 d . . . H37A H 0.4967 -0.1792 0.1432 0.108 Uiso 1 1 calc R . . C38 C 0.3751(6) -0.0933(6) 0.1908(4) 0.078(2) Uani 1 1 d . . . H38A H 0.3395 -0.1477 0.2148 0.094 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 0.069(3) 0.037(2) 0.074(3) 0.0020(19) 0.002(2) -0.0024(18) O2 0.096(3) 0.048(3) 0.098(3) -0.002(2) 0.019(3) 0.012(2) O3 0.114(4) 0.048(3) 0.120(4) 0.010(3) 0.011(4) -0.007(3) C1 0.065(4) 0.057(4) 0.069(4) 0.003(3) -0.003(3) 0.001(3) C2 0.062(4) 0.056(3) 0.054(3) -0.002(3) -0.006(3) 0.000(3) C3 0.065(4) 0.048(4) 0.058(3) -0.002(3) -0.010(3) -0.006(3) C4 0.075(4) 0.044(4) 0.075(4) 0.008(3) -0.011(4) -0.010(3) C5 0.075(4) 0.045(3) 0.076(4) -0.004(3) -0.012(3) 0.000(3) C6 0.061(3) 0.046(3) 0.063(3) -0.004(3) -0.008(3) 0.001(3) C7 0.058(3) 0.041(3) 0.062(4) 0.003(3) -0.005(3) -0.003(3) C8 0.063(5) 0.057(5) 0.056(4) -0.003(2) -0.010(4) 0.004(2) C9 0.068(4) 0.050(4) 0.077(4) -0.005(3) 0.004(3) 0.003(3) C10 0.078(4) 0.067(4) 0.081(4) -0.005(3) 0.005(4) -0.010(3) C11 0.070(4) 0.097(6) 0.066(4) -0.009(4) 0.005(3) -0.003(4) C12 0.077(5) 0.075(6) 0.077(5) -0.004(4) 0.005(4) 0.020(5) C13 0.081(4) 0.053(4) 0.081(4) -0.005(3) -0.004(4) 0.011(3) C14 0.071(5) 0.074(6) 0.054(4) 0.010(3) -0.008(4) -0.011(3) C15 0.084(5) 0.080(5) 0.080(4) 0.017(4) 0.007(4) -0.005(4) C16 0.098(6) 0.096(7) 0.112(6) 0.038(5) 0.011(5) -0.011(5) C17 0.083(6) 0.141(8) 0.065(5) 0.008(6) 0.001(4) -0.016(6) C18 0.083(5) 0.134(8) 0.064(4) -0.012(5) 0.007(4) -0.006(5) C19 0.071(5) 0.086(5) 0.069(4) -0.007(4) -0.003(4) -0.004(4) O4 0.067(3) 0.040(2) 0.072(3) 0.003(2) 0.007(2) -0.0029(17) O5 0.096(3) 0.055(3) 0.098(3) 0.000(2) 0.021(3) -0.011(3) O6 0.116(4) 0.044(3) 0.118(4) -0.013(2) 0.017(4) 0.012(3) C20 0.075(4) 0.046(4) 0.061(3) 0.006(3) 0.002(3) 0.001(3) C21 0.065(4) 0.053(3) 0.059(4) -0.003(3) -0.009(3) 0.008(4) C22 0.064(4) 0.041(4) 0.062(3) -0.005(3) -0.005(3) 0.004(3) C23 0.081(5) 0.047(4) 0.073(4) 0.001(3) -0.010(4) 0.003(3) C24 0.083(4) 0.039(3) 0.077(4) 0.003(3) -0.004(3) -0.004(3) C25 0.063(3) 0.039(3) 0.061(3) 0.004(3) -0.011(3) -0.001(3) C26 0.070(4) 0.035(3) 0.061(3) 0.004(3) -0.009(4) -0.002(3) C27 0.060(5) 0.038(4) 0.065(4) 0.002(2) -0.009(4) -0.002(2) C28 0.069(4) 0.057(4) 0.074(4) 0.006(3) -0.006(3) -0.016(3) C29 0.071(4) 0.084(6) 0.077(4) 0.012(5) 0.003(4) -0.008(5) C30 0.069(4) 0.091(6) 0.084(5) -0.005(4) 0.004(4) 0.003(4) C31 0.082(4) 0.060(4) 0.089(4) 0.000(3) 0.010(4) 0.002(3) C32 0.067(4) 0.052(3) 0.078(4) 0.004(3) 0.003(3) -0.008(3) C33 0.059(5) 0.069(5) 0.056(4) -0.010(3) -0.005(4) 0.005(3) C34 0.078(4) 0.088(5) 0.066(4) -0.001(4) 0.007(4) 0.003(4) C35 0.083(5) 0.123(8) 0.087(5) 0.006(5) 0.015(5) 0.002(5) C36 0.073(6) 0.180(11) 0.069(5) -0.018(7) 0.008(4) 0.018(7) C37 0.079(5) 0.116(7) 0.075(4) -0.026(5) -0.004(4) 0.028(4) C38 0.083(5) 0.072(5) 0.080(5) -0.012(4) 0.003(4) 0.010(4) _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 C7 1.385(8) . ? O1 C1 1.400(8) . ? O2 C1 1.206(7) . ? O3 C4 1.209(8) . ? C1 C2 1.494(10) . ? C2 C3 1.370(9) . ? C2 C14 1.460(12) . ? C3 C7 1.400(9) . ? C3 C4 1.485(9) . ? C4 C5 1.515(9) . ? C5 C6 1.537(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.348(9) . ? C6 C8 1.447(11) . ? C8 C9 1.388(8) . ? C8 C13 1.391(10) . ? C9 C10 1.375(9) . ? C9 H9A 0.9300 . ? C10 C11 1.383(10) . ? C10 H10A 0.9300 . ? C11 C12 1.377(11) . ? C11 H11A 0.9300 . ? C12 C13 1.384(11) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.399(10) . ? C14 C19 1.396(11) . ? C15 C16 1.381(10) . ? C15 H15A 0.9300 . ? C16 C17 1.378(12) . ? C16 H16A 0.9300 . ? C17 C18 1.356(12) . ? C17 H17A 0.9300 . ? C18 C19 1.398(12) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? O4 C26 1.376(7) . ? O4 C20 1.407(8) . ? O5 C20 1.204(7) . ? O6 C23 1.226(8) . ? C20 C21 1.484(9) . ? C21 C22 1.360(10) . ? C21 C33 1.457(11) . ? C22 C26 1.414(10) . ? C22 C23 1.483(9) . ? C23 C24 1.498(9) . ? C24 C25 1.514(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.333(9) . ? C25 C27 1.453(11) . ? C27 C32 1.404(8) . ? C27 C28 1.406(10) . ? C28 C29 1.369(10) . ? C28 H28A 0.9300 . ? C29 C30 1.374(11) . ? C29 H29A 0.9300 . ? C30 C31 1.384(10) . ? C30 H30A 0.9300 . ? C31 C32 1.362(9) . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? C33 C38 1.395(9) . ? C33 C34 1.403(11) . ? C34 C35 1.360(11) . ? C34 H34A 0.9300 . ? C35 C36 1.389(13) . ? C35 H35A 0.9300 . ? C36 C37 1.359(13) . ? C36 H36A 0.9300 . ? C37 C38 1.392(10) . ? C37 H37A 0.9300 . ? C38 H38A 0.9300 . ? 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 C7 O1 C1 105.8(5) . . ? O2 C1 O1 118.3(6) . . ? O2 C1 C2 132.2(6) . . ? O1 C1 C2 109.5(5) . . ? C3 C2 C14 132.6(7) . . ? C3 C2 C1 103.7(6) . . ? C14 C2 C1 123.8(6) . . ? C2 C3 C7 110.7(6) . . ? C2 C3 C4 144.0(7) . . ? C7 C3 C4 105.3(6) . . ? O3 C4 C3 128.8(7) . . ? O3 C4 C5 124.9(6) . . ? C3 C4 C5 106.3(5) . . ? C4 C5 C6 106.1(5) . . ? C4 C5 H5A 110.5 . . ? C6 C5 H5A 110.5 . . ? C4 C5 H5B 110.5 . . ? C6 C5 H5B 110.5 . . ? H5A C5 H5B 108.7 . . ? C7 C6 C8 131.8(6) . . ? C7 C6 C5 104.3(5) . . ? C8 C6 C5 123.9(5) . . ? C6 C7 O1 131.7(6) . . ? C6 C7 C3 118.0(6) . . ? O1 C7 C3 110.3(6) . . ? C9 C8 C13 118.4(7) . . ? C9 C8 C6 121.6(6) . . ? C13 C8 C6 120.0(6) . . ? C10 C9 C8 120.3(6) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 C11 120.4(7) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 120.5(7) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 118.7(7) . . ? C11 C12 H12A 120.7 . . ? C13 C12 H12A 120.7 . . ? C12 C13 C8 121.7(7) . . ? C12 C13 H13A 119.2 . . ? C8 C13 H13A 119.2 . . ? C15 C14 C19 118.9(8) . . ? C15 C14 C2 118.7(7) . . ? C19 C14 C2 122.4(7) . . ? C16 C15 C14 120.7(8) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C17 C16 C15 118.9(8) . . ? C17 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? C18 C17 C16 121.9(8) . . ? C18 C17 H17A 119.0 . . ? C16 C17 H17A 119.0 . . ? C17 C18 C19 119.8(8) . . ? C17 C18 H18A 120.1 . . ? C19 C18 H18A 120.1 . . ? C18 C19 C14 119.7(8) . . ? C18 C19 H19A 120.2 . . ? C14 C19 H19A 120.2 . . ? C26 O4 C20 106.0(5) . . ? O5 C20 O4 119.1(6) . . ? O5 C20 C21 131.8(6) . . ? O4 C20 C21 109.0(5) . . ? C22 C21 C33 131.5(7) . . ? C22 C21 C20 104.8(6) . . ? C33 C21 C20 123.8(6) . . ? C21 C22 C26 109.9(6) . . ? C21 C22 C23 145.0(7) . . ? C26 C22 C23 105.1(6) . . ? O6 C23 C22 128.0(7) . . ? O6 C23 C24 125.0(6) . . ? C22 C23 C24 106.9(5) . . ? C23 C24 C25 105.3(5) . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24B 110.7 . . ? C25 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C26 C25 C27 129.8(6) . . ? C26 C25 C24 106.7(6) . . ? C27 C25 C24 123.4(5) . . ? C25 C26 O4 133.7(7) . . ? C25 C26 C22 116.0(6) . . ? O4 C26 C22 110.3(6) . . ? C32 C27 C28 116.8(7) . . ? C32 C27 C25 122.6(6) . . ? C28 C27 C25 120.6(5) . . ? C29 C28 C27 121.1(7) . . ? C29 C28 H28A 119.4 . . ? C27 C28 H28A 119.4 . . ? C30 C29 C28 121.0(7) . . ? C30 C29 H29A 119.5 . . ? C28 C29 H29A 119.5 . . ? C29 C30 C31 118.7(7) . . ? C29 C30 H30A 120.6 . . ? C31 C30 H30A 120.6 . . ? C32 C31 C30 121.1(7) . . ? C32 C31 H31A 119.5 . . ? C30 C31 H31A 119.5 . . ? C31 C32 C27 121.2(6) . . ? C31 C32 H32A 119.4 . . ? C27 C32 H32A 119.4 . . ? C38 C33 C34 118.2(8) . . ? C38 C33 C21 119.6(7) . . ? C34 C33 C21 122.2(7) . . ? C35 C34 C33 120.6(8) . . ? C35 C34 H34A 119.7 . . ? C33 C34 H34A 119.7 . . ? C34 C35 C36 121.6(9) . . ? C34 C35 H35A 119.2 . . ? C36 C35 H35A 119.2 . . ? C37 C36 C35 118.0(8) . . ? C37 C36 H36A 121.0 . . ? C35 C36 H36A 121.0 . . ? C36 C37 C38 122.2(8) . . ? C36 C37 H37A 118.9 . . ? C38 C37 H37A 118.9 . . ? C33 C38 C37 119.4(8) . . ? C33 C38 H38A 120.3 . . ? C37 C38 H38A 120.3 . . ? 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 C7 O1 C1 O2 -178.7(6) . . . . ? C7 O1 C1 C2 -0.8(6) . . . . ? O2 C1 C2 C3 178.4(7) . . . . ? O1 C1 C2 C3 0.8(6) . . . . ? O2 C1 C2 C14 -2.1(12) . . . . ? O1 C1 C2 C14 -179.6(6) . . . . ? C14 C2 C3 C7 179.9(7) . . . . ? C1 C2 C3 C7 -0.6(7) . . . . ? C14 C2 C3 C4 0.6(14) . . . . ? C1 C2 C3 C4 -179.9(8) . . . . ? C2 C3 C4 O3 -3.3(14) . . . . ? C7 C3 C4 O3 177.4(7) . . . . ? C2 C3 C4 C5 179.1(7) . . . . ? C7 C3 C4 C5 -0.3(7) . . . . ? O3 C4 C5 C6 -177.4(7) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 C7 -0.3(6) . . . . ? C4 C5 C6 C8 179.5(6) . . . . ? C8 C6 C7 O1 0.8(13) . . . . ? C5 C6 C7 O1 -179.4(7) . . . . ? C8 C6 C7 C3 -179.6(6) . . . . ? C5 C6 C7 C3 0.2(8) . . . . ? C1 O1 C7 C6 -180.0(7) . . . . ? C1 O1 C7 C3 0.4(7) . . . . ? C2 C3 C7 C6 -179.5(6) . . . . ? C4 C3 C7 C6 0.0(8) . . . . ? C2 C3 C7 O1 0.1(7) . . . . ? C4 C3 C7 O1 179.7(5) . . . . ? C7 C6 C8 C9 1.8(13) . . . . ? C5 C6 C8 C9 -177.9(6) . . . . ? C7 C6 C8 C13 179.2(6) . . . . ? C5 C6 C8 C13 -0.6(11) . . . . ? C13 C8 C9 C10 -1.9(11) . . . . ? C6 C8 C9 C10 175.5(6) . . . . ? C8 C9 C10 C11 0.7(10) . . . . ? C9 C10 C11 C12 0.4(10) . . . . ? C10 C11 C12 C13 -0.3(10) . . . . ? C11 C12 C13 C8 -1.0(10) . . . . ? C9 C8 C13 C12 2.1(11) . . . . ? C6 C8 C13 C12 -175.3(7) . . . . ? C3 C2 C14 C15 -3.8(12) . . . . ? C1 C2 C14 C15 176.8(6) . . . . ? C3 C2 C14 C19 176.6(7) . . . . ? C1 C2 C14 C19 -2.9(11) . . . . ? C19 C14 C15 C16 -0.2(12) . . . . ? C2 C14 C15 C16 -179.9(7) . . . . ? C14 C15 C16 C17 0.8(12) . . . . ? C15 C16 C17 C18 -0.7(13) . . . . ? C16 C17 C18 C19 0.1(13) . . . . ? C17 C18 C19 C14 0.4(12) . . . . ? C15 C14 C19 C18 -0.4(12) . . . . ? C2 C14 C19 C18 179.3(7) . . . . ? C26 O4 C20 O5 -178.9(6) . . . . ? C26 O4 C20 C21 -0.2(6) . . . . ? O5 C20 C21 C22 178.7(7) . . . . ? O4 C20 C21 C22 0.1(6) . . . . ? O5 C20 C21 C33 -1.2(11) . . . . ? O4 C20 C21 C33 -179.7(6) . . . . ? C33 C21 C22 C26 179.8(7) . . . . ? C20 C21 C22 C26 0.0(7) . . . . ? C33 C21 C22 C23 -2.1(14) . . . . ? C20 C21 C22 C23 178.0(9) . . . . ? C21 C22 C23 O6 3.4(15) . . . . ? C26 C22 C23 O6 -178.5(7) . . . . ? C21 C22 C23 C24 -178.8(8) . . . . ? C26 C22 C23 C24 -0.6(7) . . . . ? O6 C23 C24 C25 178.6(7) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C23 C24 C25 C27 179.2(6) . . . . ? C27 C25 C26 O4 -0.4(14) . . . . ? C24 C25 C26 O4 179.2(8) . . . . ? C27 C25 C26 C22 -179.6(6) . . . . ? C24 C25 C26 C22 -0.1(8) . . . . ? C20 O4 C26 C25 -179.1(8) . . . . ? C20 O4 C26 C22 0.2(7) . . . . ? C21 C22 C26 C25 179.3(6) . . . . ? C23 C22 C26 C25 0.5(8) . . . . ? C21 C22 C26 O4 -0.1(8) . . . . ? C23 C22 C26 O4 -179.0(6) . . . . ? C26 C25 C27 C32 -4.0(12) . . . . ? C24 C25 C27 C32 176.5(6) . . . . ? C26 C25 C27 C28 176.1(6) . . . . ? C24 C25 C27 C28 -3.4(10) . . . . ? C32 C27 C28 C29 1.5(10) . . . . ? C25 C27 C28 C29 -178.6(6) . . . . ? C27 C28 C29 C30 0.3(10) . . . . ? C28 C29 C30 C31 -2.2(10) . . . . ? C29 C30 C31 C32 2.3(10) . . . . ? C30 C31 C32 C27 -0.5(10) . . . . ? C28 C27 C32 C31 -1.4(10) . . . . ? C25 C27 C32 C31 178.7(7) . . . . ? C22 C21 C33 C38 -11.8(12) . . . . ? C20 C21 C33 C38 168.0(6) . . . . ? C22 C21 C33 C34 169.4(7) . . . . ? C20 C21 C33 C34 -10.7(11) . . . . ? C38 C33 C34 C35 -0.5(12) . . . . ? C21 C33 C34 C35 178.3(7) . . . . ? C33 C34 C35 C36 0.2(12) . . . . ? C34 C35 C36 C37 -0.1(13) . . . . ? C35 C36 C37 C38 0.3(12) . . . . ? C34 C33 C38 C37 0.7(11) . . . . ? C21 C33 C38 C37 -178.1(6) . . . . ? C36 C37 C38 C33 -0.7(12) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.379 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.142