# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 152459 data_py004_0 _database_code_CSD 152459 _journal_coden_Cambridge 207 _audit_creation_method SHELXL-97 _audit_author_name 'Dr Ian J. Scowen' _audit_contact_author 'Dr Ian J. Scowen' _audit_contact_author_address ; Chemical and Forensic Sciences University of Bradford BRADFORD BD7 1DP United Kingdom ; _audit_contact_author_email i.scowen@bradford.ac.uk _audit_contact_author_fax '01274 235350 ' _audit_contact_author_phone '01274 233764' _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 1' _publ_section_title ; Metabolites of the Higher Fungi. Part 32.1 Rosenecatrone, a phytotoxic bicyclo[4,1,0]hept-3-en-2-one from the fungus Rosellinia necatrix Prill. ; _publ_contact_author 'Dr Raymond L. Edwards' _publ_contact_author_address ; Chemical and Forensic Sciences University of Bradford BRADFORD BD7 1DP United Kingdom ; loop_ _publ_author_name 'De Sousa, Antonio J. T.' 'Edwards, R.' 'Maitland, D.' 'Scowen, Ian J.' 'Whalley, Anthony J. S.' _chemical_name_systematic ; ? ; _chemical_name_common 'rosnecatrol tetraacetate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 O9' _chemical_formula_weight 450.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.3738(17) _cell_length_b 8.5966(17) _cell_length_c 10.291(2) _cell_angle_alpha 67.40(3) _cell_angle_beta 75.08(3) _cell_angle_gamma 67.33(3) _cell_volume 625.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.477 _exptl_crystal_size_mid 0.347 _exptl_crystal_size_min 0.347 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.771 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type 'CuK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Planar graphite' _diffrn_radiation_collimation '0.8 mm' _diffrn_radiation_detector 'NaI(Tl) Scintillation Counter' _diffrn_radiation_polarisn_norm 90.0 _diffrn_radiation_polarisn_ratio 0.9560 _diffrn_measurement_device_type 'Stoe STADI-4 four-circle' _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2112 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0096 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.69 _diffrn_reflns_theta_max 59.99 _reflns_number_total 2108 _reflns_number_gt 2009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4 6.2D' _computing_cell_refinement 'Stoe DIF4 6.2D' _computing_data_reduction 'XRED 1.05 (Stoe 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'WIN-GX (Farrugia, 1999)' _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^)+(0.0518P)^2^+0.1002P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0258(19) _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 0.2(3) _refine_ls_number_reflns 2108 _refine_ls_number_parameters 306 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.001 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 O7 O 0.5155(3) 0.5136(3) 0.4216(2) 0.0660(6) Uani 1 1 d . . . O8 O 0.4428(3) 0.1311(3) 0.3979(3) 0.0712(6) Uani 1 1 d . . . O81 O 0.3790(5) 0.1740(5) 0.1861(4) 0.1091(10) Uani 1 1 d . . . O51 O 0.5674(3) 0.2123(3) 0.7898(3) 0.0733(6) Uani 1 1 d . . . O52 O 0.7988(5) 0.2558(5) 0.8157(5) 0.1392(17) Uani 1 1 d . . . O161 O 0.2988(3) 0.7069(3) 0.7936(3) 0.0768(7) Uani 1 1 d . . . O162 O 0.1932(6) 0.7286(5) 1.0070(4) 0.1348(14) Uani 1 1 d . . . O21 O 0.1551(3) 0.5237(3) 0.4086(2) 0.0662(6) Uani 1 1 d . . . O22 O 0.0040(4) 0.3350(5) 0.4604(4) 0.1072(10) Uani 1 1 d . . . C1 C 0.4486(4) 0.3683(4) 0.4567(3) 0.0576(7) Uani 1 1 d . . . C6 C 0.5763(4) 0.3556(4) 0.5385(4) 0.0635(8) Uani 1 1 d . . . C5 C 0.5195(4) 0.3850(4) 0.6806(4) 0.0640(8) Uani 1 1 d . . . C4 C 0.3254(4) 0.4703(4) 0.7146(3) 0.0609(8) Uani 1 1 d . . . C3 C 0.2083(4) 0.4818(4) 0.6406(3) 0.0572(7) Uani 1 1 d . . . C2 C 0.2618(4) 0.4028(4) 0.5219(3) 0.0557(7) Uani 1 1 d . . . C8 C 0.5012(4) 0.2873(4) 0.3374(4) 0.0635(8) Uani 1 1 d . . . C81 C 0.3829(5) 0.0907(5) 0.3093(5) 0.0794(10) Uani 1 1 d . . . C82 C 0.3203(8) -0.0657(6) 0.3857(7) 0.1222(19) Uani 1 1 d . . . H82A H 0.2077 -0.0294 0.4385 0.183 Uiso 1 1 calc R . . H82B H 0.4012 -0.1551 0.4496 0.183 Uiso 1 1 calc R . . H82C H 0.3117 -0.1134 0.3183 0.183 Uiso 1 1 calc R . . C9 C 0.6915(5) 0.2322(5) 0.2843(4) 0.0727(9) Uani 1 1 d . . . C10 C 0.7686(5) 0.3190(6) 0.1651(4) 0.0770(10) Uani 1 1 d . . . C12 C 0.6754(7) 0.4948(7) 0.0663(5) 0.1090(15) Uani 1 1 d . . . H12A H 0.6056 0.4774 0.0155 0.164 Uiso 1 1 calc R . . H12B H 0.7593 0.5471 0.0001 0.164 Uiso 1 1 calc R . . H12C H 0.6015 0.5725 0.1199 0.164 Uiso 1 1 calc R . . C11 C 0.9607(6) 0.2465(9) 0.1212(6) 0.1167(17) Uani 1 1 d . . . H11A H 1.0068 0.1291 0.1852 0.175 Uiso 1 1 calc R . . H11B H 1.0182 0.3226 0.1235 0.175 Uiso 1 1 calc R . . H11C H 0.9799 0.2413 0.0266 0.175 Uiso 1 1 calc R . . C51 C 0.7081(5) 0.1661(5) 0.8535(4) 0.0775(10) Uani 1 1 d . . . C52 C 0.7329(7) -0.0047(7) 0.9698(5) 0.1027(14) Uani 1 1 d . . . H52A H 0.7959 -0.0076 1.0370 0.154 Uiso 1 1 calc R . . H52B H 0.7978 -0.1008 0.9320 0.154 Uiso 1 1 calc R . . H52C H 0.6211 -0.0169 1.0162 0.154 Uiso 1 1 calc R . . C16 C 0.2738(5) 0.5335(5) 0.8406(4) 0.0694(8) Uani 1 1 d . . . C161 C 0.2494(5) 0.7917(5) 0.8881(5) 0.0794(10) Uani 1 1 d . . . C162 C 0.2686(7) 0.9723(6) 0.8263(6) 0.1066(16) Uani 1 1 d . . . H16A H 0.1614 1.0582 0.7929 0.160 Uiso 1 1 calc R . . H16B H 0.3611 0.9738 0.7485 0.160 Uiso 1 1 calc R . . H16C H 0.2956 1.0013 0.8977 0.160 Uiso 1 1 calc R . . C13 C 0.0170(4) 0.5617(4) 0.6716(4) 0.0646(8) Uani 1 1 d . . . C14 C -0.0687(5) 0.7281(5) 0.6555(5) 0.0866(12) Uani 1 1 d . . . C15 C -0.2661(5) 0.8044(6) 0.6754(6) 0.1019(14) Uani 1 1 d . . . H15A H -0.3151 0.7092 0.7130 0.153 Uiso 1 1 calc R . . H15B H -0.3059 0.8812 0.5855 0.153 Uiso 1 1 calc R . . H15C H -0.3024 0.8711 0.7402 0.153 Uiso 1 1 calc R . . C21 C 0.0241(4) 0.4764(6) 0.3939(4) 0.0783(10) Uani 1 1 d . . . C22 C -0.0891(6) 0.6279(8) 0.2916(6) 0.1166(17) Uani 1 1 d . . . H22A H -0.1856 0.5968 0.2870 0.175 Uiso 1 1 calc R . . H22B H -0.0226 0.6539 0.1994 0.175 Uiso 1 1 calc R . . H22C H -0.1322 0.7306 0.3225 0.175 Uiso 1 1 calc R . . H9 H 0.7539 0.0986 0.3554 0.101(13) Uiso 1 1 d . . . H8 H 0.4240 0.3842 0.2574 0.069(9) Uiso 1 1 d . . . H13 H -0.0576 0.4939 0.6832 0.107(15) Uiso 1 1 d . . . H161 H 0.3416 0.4540 0.9211 0.078(11) Uiso 1 1 d . . . H162 H 0.1520 0.5691 0.8855 0.108(14) Uiso 1 1 d . . . H6 H 0.7172 0.2854 0.5224 0.075(10) Uiso 1 1 d . . . H2 H 0.2236 0.2913 0.5527 0.059(8) Uiso 1 1 d . . . H14 H 0.0022 0.8244 0.6259 0.102(13) Uiso 1 1 d . . . H5 H 0.5856 0.4566 0.6862 0.056(8) Uiso 1 1 d . . . 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 O7 0.0631(12) 0.0558(11) 0.0723(14) -0.0065(10) -0.0058(10) -0.0276(9) O8 0.0757(14) 0.0592(12) 0.0740(15) -0.0160(11) -0.0072(12) -0.0234(11) O81 0.134(3) 0.117(2) 0.093(2) -0.027(2) -0.028(2) -0.057(2) O51 0.0769(15) 0.0617(13) 0.0795(16) -0.0045(12) -0.0310(13) -0.0252(11) O52 0.126(3) 0.149(3) 0.145(3) 0.027(3) -0.075(3) -0.083(2) O161 0.0891(16) 0.0746(14) 0.0711(15) -0.0262(12) 0.0040(13) -0.0370(12) O162 0.186(4) 0.123(3) 0.094(2) -0.052(2) 0.034(3) -0.064(3) O21 0.0547(11) 0.0761(13) 0.0607(13) -0.0130(11) -0.0096(9) -0.0212(10) O22 0.0912(19) 0.117(2) 0.133(3) -0.034(2) -0.0243(19) -0.0529(18) C1 0.0530(15) 0.0470(14) 0.0625(18) -0.0037(13) -0.0097(14) -0.0177(12) C6 0.0538(16) 0.0582(17) 0.071(2) -0.0083(15) -0.0079(15) -0.0225(13) C5 0.0628(18) 0.0582(17) 0.071(2) -0.0088(16) -0.0175(16) -0.0258(14) C4 0.0669(18) 0.0549(16) 0.0574(18) -0.0097(14) -0.0090(16) -0.0237(14) C3 0.0538(16) 0.0537(16) 0.0558(17) -0.0050(14) -0.0086(14) -0.0202(13) C2 0.0513(15) 0.0524(15) 0.0558(17) -0.0070(13) -0.0107(13) -0.0165(12) C8 0.0594(17) 0.0561(17) 0.0656(19) -0.0117(15) -0.0063(15) -0.0178(13) C81 0.072(2) 0.067(2) 0.099(3) -0.031(2) -0.014(2) -0.0152(16) C82 0.152(5) 0.079(3) 0.153(5) -0.027(3) -0.039(4) -0.052(3) C9 0.0637(18) 0.075(2) 0.068(2) -0.0191(18) -0.0055(17) -0.0163(15) C10 0.070(2) 0.103(3) 0.066(2) -0.035(2) 0.0032(17) -0.0367(19) C12 0.124(4) 0.117(3) 0.072(3) -0.003(3) -0.005(3) -0.056(3) C11 0.078(3) 0.183(5) 0.094(3) -0.059(4) 0.010(2) -0.047(3) C51 0.070(2) 0.085(2) 0.074(2) -0.0178(19) -0.0226(19) -0.0198(18) C52 0.107(3) 0.094(3) 0.087(3) -0.009(2) -0.038(3) -0.016(2) C16 0.075(2) 0.072(2) 0.0580(19) -0.0092(16) -0.0099(17) -0.0304(16) C161 0.066(2) 0.083(2) 0.084(3) -0.036(2) 0.0051(19) -0.0181(17) C162 0.106(3) 0.084(3) 0.135(4) -0.055(3) 0.015(3) -0.035(2) C13 0.0579(17) 0.0696(19) 0.0606(19) -0.0162(16) -0.0043(15) -0.0213(15) C14 0.075(2) 0.070(2) 0.095(3) -0.015(2) 0.000(2) -0.0216(18) C15 0.070(2) 0.092(3) 0.107(3) -0.025(3) -0.008(2) 0.004(2) C21 0.0551(18) 0.111(3) 0.070(2) -0.031(2) -0.0072(16) -0.0263(19) C22 0.078(3) 0.172(5) 0.089(3) -0.020(3) -0.032(2) -0.037(3) _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 O7 C6 1.442(4) . ? O7 C1 1.447(4) . ? O8 C81 1.348(5) . ? O8 C8 1.462(4) . ? O81 C81 1.194(5) . ? O51 C51 1.346(4) . ? O51 C5 1.456(4) . ? O52 C51 1.179(5) . ? O161 C161 1.324(5) . ? O161 C16 1.461(4) . ? O162 C161 1.185(5) . ? O21 C21 1.367(4) . ? O21 C2 1.458(4) . ? O22 C21 1.197(5) . ? C1 C6 1.472(5) . ? C1 C2 1.497(4) . ? C1 C8 1.525(5) . ? C6 C5 1.504(5) . ? C6 H6 1.100(3) . ? C5 C4 1.513(5) . ? C5 H5 0.997(3) . ? C4 C3 1.343(4) . ? C4 C16 1.496(5) . ? C3 C13 1.482(4) . ? C3 C2 1.508(5) . ? C2 H2 1.035(3) . ? C8 C9 1.493(5) . ? C8 H8 1.059(3) . ? C81 C82 1.490(6) . ? C82 H82A 0.9600 . ? C82 H82B 0.9600 . ? C82 H82C 0.9600 . ? C9 C10 1.318(5) . ? C9 H9 1.103(4) . ? C10 C12 1.499(7) . ? C10 C11 1.500(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C51 C52 1.474(6) . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C16 H161 0.991(3) . ? C16 H162 0.986(4) . ? C161 C162 1.491(6) . ? C162 H16A 0.9600 . ? C162 H16B 0.9600 . ? C162 H16C 0.9600 . ? C13 C14 1.295(5) . ? C13 H13 0.966(3) . ? C14 C15 1.516(5) . ? C14 H14 1.105(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C21 C22 1.487(7) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C6 O7 C1 61.26(19) . . ? C81 O8 C8 116.9(3) . . ? C51 O51 C5 118.2(3) . . ? C161 O161 C16 116.9(3) . . ? C21 O21 C2 117.5(3) . . ? O7 C1 C6 59.19(19) . . ? O7 C1 C2 114.9(2) . . ? C6 C1 C2 118.1(3) . . ? O7 C1 C8 112.0(2) . . ? C6 C1 C8 122.6(3) . . ? C2 C1 C8 115.9(3) . . ? O7 C6 C1 59.55(19) . . ? O7 C6 C5 113.6(3) . . ? C1 C6 C5 121.0(3) . . ? O7 C6 H6 113.6(3) . . ? C1 C6 H6 124.2(3) . . ? C5 C6 H6 112.0(3) . . ? O51 C5 C6 108.0(3) . . ? O51 C5 C4 106.4(3) . . ? C6 C5 C4 115.2(3) . . ? O51 C5 H5 108.1(3) . . ? C6 C5 H5 108.3(3) . . ? C4 C5 H5 110.7(3) . . ? C3 C4 C16 122.7(3) . . ? C3 C4 C5 122.5(3) . . ? C16 C4 C5 114.8(3) . . ? C4 C3 C13 124.2(3) . . ? C4 C3 C2 121.9(3) . . ? C13 C3 C2 113.8(3) . . ? O21 C2 C1 107.2(2) . . ? O21 C2 C3 108.4(2) . . ? C1 C2 C3 116.5(3) . . ? O21 C2 H2 101.4(2) . . ? C1 C2 H2 111.8(3) . . ? C3 C2 H2 110.3(3) . . ? O8 C8 C9 109.4(3) . . ? O8 C8 C1 104.3(2) . . ? C9 C8 C1 116.0(3) . . ? O8 C8 H8 109.3(3) . . ? C9 C8 H8 113.0(3) . . ? C1 C8 H8 104.3(2) . . ? O81 C81 O8 123.1(4) . . ? O81 C81 C82 125.5(4) . . ? O8 C81 C82 111.3(4) . . ? C81 C82 H82A 109.5 . . ? C81 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C81 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C10 C9 C8 126.0(4) . . ? C10 C9 H9 125.5(3) . . ? C8 C9 H9 108.1(3) . . ? C9 C10 C12 123.7(4) . . ? C9 C10 C11 120.9(4) . . ? C12 C10 C11 115.3(4) . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O52 C51 O51 121.6(4) . . ? O52 C51 C52 126.0(4) . . ? O51 C51 C52 112.5(4) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O161 C16 C4 107.4(3) . . ? O161 C16 H161 108.3(3) . . ? C4 C16 H161 114.7(3) . . ? O161 C16 H162 97.3(3) . . ? C4 C16 H162 122.7(3) . . ? H161 C16 H162 104.5(3) . . ? O162 C161 O161 122.2(4) . . ? O162 C161 C162 125.3(4) . . ? O161 C161 C162 112.5(4) . . ? C161 C162 H16A 109.5 . . ? C161 C162 H16B 109.5 . . ? H16A C162 H16B 109.5 . . ? C161 C162 H16C 109.5 . . ? H16A C162 H16C 109.5 . . ? H16B C162 H16C 109.5 . . ? C14 C13 C3 126.7(3) . . ? C14 C13 H13 112.6(3) . . ? C3 C13 H13 118.9(3) . . ? C13 C14 C15 124.1(4) . . ? C13 C14 H14 120.1(3) . . ? C15 C14 H14 115.8(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O22 C21 O21 123.1(3) . . ? O22 C21 C22 127.0(4) . . ? O21 C21 C22 109.9(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.125 _refine_diff_density_min -0.115 _refine_diff_density_rms 0.029