# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002data_1 _database_code_CSD 192411 _audit_creation_date 02-03-05 _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _journal_coden_Cambridge 207 loop_ _publ_author_name 'Martin G. Banwell' 'Alison J. Edwards' 'Gwion Harfoot' 'Martin G. Banwell' 'Katrina A. Jolliffe' _publ_contact_author_name 'Prof Martin G. Banwell' _publ_contact_author_address ; Research School of Chemistry Australian National University Science Road ACTON ACT 2601 AUSTRALIA ; _publ_contact_author_email 'MGB@RSC.ANU.EDU.AU' _publ_contact_author_fax ' ?' _publ_contact_author_phone ' ?' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; A chemoenzymatic synthesis of ()-hirsutene from toluene ; _publ_section_exptl_refinement ; The material presented for this study consisted of a range of crystal sizes. Attractive larger specimens (all dimensions > 0.3mm) were found to be twinned. A well formed small needle with no apparent twinning was used in this experiment but the resolution of the structure is limited by the limited maximum diffraction angle. Owing to the homochiral sample, the material is necessarily noncentrosymmetric leading to a lower than desirable reflection/parameter ratio. This is unavoidable. The absolute stereochemistry depicted in this structure is assigned on the postulate that this is known from the synthetic pathway. ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'needle' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'mixed' # Submission details _publ_requested_journal 'Acta Crystallographica Section C ' _diffrn_measurement_device 'KappaCCD' _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.13512 _diffrn_orient_matrix_UB_12 0.03956 _diffrn_orient_matrix_UB_13 -0.08452 _diffrn_orient_matrix_UB_21 -0.00289 _diffrn_orient_matrix_UB_22 -0.08385 _diffrn_orient_matrix_UB_23 -0.03462 _diffrn_orient_matrix_UB_31 -0.02230 _diffrn_orient_matrix_UB_32 -0.01169 _diffrn_orient_matrix_UB_33 0.03018 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 308.418 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C18 H28 O4 ' _chemical_formula_sum 'C18 H28 O4 ' _chemical_absolute_configuration syn _chemical_name_systematic ; ? ; _cell_length_a 6.08980(10) _cell_length_b 11.0181(2) _cell_length_c 25.4436(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1707.22(5) _diffrn_reflns_number 24086 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_full 25.03 _cell_measurement_reflns_used 22667 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_reflns_av_R_equivalents 0.04 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.180 -1 0 0 0.140 0 0 1 0.030 0 0 -1 0.050 0 1 0 0.080 0 -1 0 0.060 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_absorpt_coefficient_mu 0.083 _exptl_crystal_F_000 672 _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.32 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens mixed # Refinement statistics _reflns_d_resolution_low 1.83 _reflns_d_resolution_high 0.65 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_total 1770 _reflns_number_gt 1268 _refine_ls_matrix_type full _refine_ls_structure_factor_coef F _reflns_threshold_expression >2.00\s(I) _refine_ls_number_reflns 1268 _refine_ls_number_parameters 211 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0334 _refine_ls_goodness_of_fit_ref 1.0303 _refine_ls_shift/su_max 0.000184 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.359 0.206 0.152 ; _refine_diff_density_min -0.12 _refine_diff_density_max 0.13 _refine_diff_density_rms 0.02 _computing_structure_solution ; SIR97 (Altomare et al, 1999) ; _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) + maXus (Mackay et al 1999) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) + maXus (Mackay et al 1999) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #================================================== _publ_section_references ; COLLECT Software, Nonius BV 1997-2001) Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type O12 o -0.0616(3) 0.29857(15) 0.10129(5) 0.0459 1.0000 Uani O14 o -0.0585(3) 0.18293(15) 0.02406(6) 0.0503 1.0000 Uani O17 o 0.1839(3) -0.04052(17) 0.05072(7) 0.0647 1.0000 Uani O19 o 0.0648(4) 0.54560(18) 0.08012(8) 0.0740 1.0000 Uani C1 c 0.1599(4) 0.3379(2) 0.10329(9) 0.0426 1.0000 Uani C2 c 0.1867(5) 0.4750(2) 0.10215(9) 0.0522 1.0000 Uani C3 c 0.3897(5) 0.5035(2) 0.1308(1) 0.0559 1.0000 Uani C4 c 0.3827(5) 0.4892(2) 0.1906(1) 0.0521 1.0000 Uani C5 c 0.1696(4) 0.4524(2) 0.21747(8) 0.0436 1.0000 Uani C6 c 0.1891(5) 0.4543(2) 0.27805(8) 0.0504 1.0000 Uani C7 c 0.1216(4) 0.3281(2) 0.29736(8) 0.0453 1.0000 Uani C8 c 0.2065(4) 0.24950(19) 0.25209(8) 0.0425 1.0000 Uani C9 c 0.1394(4) 0.31707(19) 0.20226(7) 0.0374 1.0000 Uani C10 c 0.2829(4) 0.2945(2) 0.15295(8) 0.0399 1.0000 Uani C11 c 0.4703(4) 0.3880(2) 0.1577(1) 0.0498 1.0000 Uani C13 c -0.1446(4) 0.2857(2) 0.04949(8) 0.0505 1.0000 Uani C15 c -0.1470(5) 0.0715(2) 0.0437(1) 0.0547 1.0000 Uani C16 c -0.0161(5) -0.0324(2) 0.0229(1) 0.0571 1.0000 Uani C17 c 0.3063(6) -0.1453(3) 0.03602(12) 0.0751 1.0000 Uani C20 c 0.2270(5) 0.2953(3) 0.35000(9) 0.0600 1.0000 Uani C21 c -0.1292(4) 0.3193(3) 0.3024(1) 0.0588 1.0000 Uani C22 c 0.3590(5) 0.1634(2) 0.14685(9) 0.0533 1.0000 Uani H31 h 0.487(6) 0.561(3) 0.1193(12) 0.08(1) 1.0000 Uiso H41 h 0.489(5) 0.537(3) 0.209(1) 0.078(9) 1.0000 Uiso H111 h 0.622(5) 0.361(2) 0.155(1) 0.061(8) 1.0000 Uiso H11 h 0.2245(4) 0.3011(2) 0.07086(9) 0.0539 1.0000 Uiso H51 h 0.0479(4) 0.5078(2) 0.20644(8) 0.0550 1.0000 Uiso H61 h 0.3443(5) 0.4718(2) 0.28845(8) 0.0672 1.0000 Uiso H62 h 0.0900(5) 0.5175(2) 0.29331(8) 0.0672 1.0000 Uiso H81 h 0.3697(4) 0.24086(19) 0.25394(8) 0.0513 1.0000 Uiso H82 h 0.1370(4) 0.16729(19) 0.25305(8) 0.0513 1.0000 Uiso H91 h -0.0118(4) 0.29066(19) 0.19202(7) 0.0464 1.0000 Uiso H131 h -0.1021(4) 0.3589(2) 0.02860(8) 0.0624 1.0000 Uiso H132 h -0.3084(4) 0.2791(2) 0.05072(8) 0.0624 1.0000 Uiso H151 h -0.3042(5) 0.0639(2) 0.0328(1) 0.0706 1.0000 Uiso H152 h -0.1371(5) 0.0707(2) 0.0829(1) 0.0706 1.0000 Uiso H161 h 0.0138(5) -0.0180(2) -0.0153(1) 0.0701 1.0000 Uiso H162 h -0.1004(5) -0.1097(2) 0.0271(1) 0.0701 1.0000 Uiso H171 h 0.4459(6) -0.1464(3) 0.05671(12) 0.0895 1.0000 Uiso H172 h 0.3413(6) -0.1427(3) -0.00237(12) 0.0895 1.0000 Uiso H173 h 0.2194(6) -0.2200(3) 0.04397(12) 0.0895 1.0000 Uiso H201 h 0.1788(5) 0.2125(3) 0.36113(9) 0.0737 1.0000 Uiso H202 h 0.3904(5) 0.2967(3) 0.34616(9) 0.0737 1.0000 Uiso H203 h 0.1815(5) 0.3560(3) 0.37713(9) 0.0737 1.0000 Uiso H211 h -0.1717(4) 0.2365(3) 0.3148(1) 0.0769 1.0000 Uiso H212 h -0.1990(4) 0.3354(3) 0.2675(1) 0.0769 1.0000 Uiso H213 h -0.1803(4) 0.3813(3) 0.3283(1) 0.0769 1.0000 Uiso H221 h 0.4363(5) 0.1360(2) 0.17944(9) 0.0696 1.0000 Uiso H222 h 0.4617(5) 0.1581(2) 0.11627(9) 0.0696 1.0000 Uiso H223 h 0.2287(5) 0.1103(2) 0.14036(9) 0.0696 1.0000 Uiso 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 O12 0.0355(8) 0.063(1) 0.0391(8) -0.0037(7) -0.0010(7) 0.0004(8) O14 0.054(1) 0.055(1) 0.0413(8) -0.0028(8) 0.0049(8) -0.0027(9) O17 0.0697(13) 0.0583(11) 0.0661(11) -0.0086(9) -0.0099(11) 0.0009(11) O19 0.1002(16) 0.0571(11) 0.0647(11) 0.009(1) -0.0146(12) 0.0089(13) C1 0.0360(12) 0.0502(13) 0.0416(11) -0.001(1) 0.001(1) -0.0005(11) C2 0.0604(17) 0.0545(15) 0.0418(12) 0.0021(12) 0.0054(12) 0.0010(14) C3 0.0614(19) 0.0547(16) 0.0516(15) 0.0018(12) 0.0063(13) -0.0151(15) C4 0.0507(15) 0.0545(15) 0.0510(15) -0.0067(12) 0.0014(12) -0.0140(13) C5 0.0443(13) 0.0402(12) 0.0463(12) -0.002(1) 0.0027(11) 0.0027(12) C6 0.0580(16) 0.0485(14) 0.0448(12) -0.0064(11) -0.0004(12) -0.0023(14) C7 0.0468(13) 0.0498(13) 0.0392(11) -0.0025(11) -0.0005(11) 0.0003(12) C8 0.0401(12) 0.0423(11) 0.0453(11) 0.000(1) -0.0010(11) 0.0003(11) C9 0.0322(11) 0.0378(11) 0.0422(11) -0.003(1) 0.000(1) 0.000(1) C10 0.0349(11) 0.0440(12) 0.0408(11) -0.002(1) 0.001(1) 0.0011(11) C11 0.0374(13) 0.0600(16) 0.0521(14) -0.0053(12) 0.0039(12) -0.0066(13) C13 0.0453(14) 0.0631(15) 0.0432(12) -0.0013(11) -0.0067(12) 0.0032(14) C15 0.0548(16) 0.0564(15) 0.0530(14) -0.0012(12) 0.0031(13) -0.0077(14) C16 0.0621(18) 0.0578(15) 0.0513(13) -0.0085(13) -0.0035(13) -0.0084(14) C17 0.076(2) 0.0627(18) 0.086(2) 0.0026(15) 0.0072(18) 0.0082(18) C20 0.0678(17) 0.0679(16) 0.0443(13) 0.0007(12) -0.0054(13) 0.0048(16) C21 0.0496(15) 0.0668(17) 0.0600(15) -0.0041(14) 0.0091(13) -0.0004(14) C22 0.0553(15) 0.0544(14) 0.0501(13) -0.0073(11) -0.0002(13) 0.0131(13) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O12 . C1 . 1.418(3) yes O12 . C13 . 1.419(3) yes O14 . C13 . 1.406(3) yes O14 . C15 . 1.432(3) yes O17 . C16 . 1.412(3) yes O17 . C17 . 1.424(3) yes O19 . C2 . 1.213(3) yes C1 . C2 . 1.520(4) yes C1 . C10 . 1.545(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.469(4) yes C3 . C4 . 1.531(4) yes C3 . C11 . 1.526(4) yes C3 . H31 . 0.92(3) yes C4 . C5 . 1.521(3) yes C4 . C11 . 1.492(4) yes C4 . H41 . 0.95(3) yes C5 . C6 . 1.546(3) yes C5 . C9 . 1.551(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.531(3) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.531(3) yes C7 . C20 . 1.529(3) yes C7 . C21 . 1.536(4) yes C8 . C9 . 1.526(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C10 . 1.549(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.543(3) yes C10 . C22 . 1.524(3) yes C11 . H111 . 0.98(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C15 . C16 . 1.492(4) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O12 . C13 . 113.78(18) yes C13 . O14 . C15 . 112.94(17) yes C16 . O17 . C17 . 111.8(2) yes O12 . C1 . C2 . 113.9(2) yes O12 . C1 . C10 . 113.36(18) yes C2 . C1 . C10 . 105.73(19) yes O12 . C1 . H11 . 102.76(12) no C2 . C1 . H11 . 110.18(13) no C10 . C1 . H11 . 111.02(12) no O19 . C2 . C1 . 125.5(3) yes O19 . C2 . C3 . 127.4(2) yes C1 . C2 . C3 . 107.0(2) yes C2 . C3 . C4 . 116.6(2) yes C2 . C3 . C11 . 108.4(2) yes C4 . C3 . C11 . 58.44(17) yes C2 . C3 . H31 . 122.3(20) yes C4 . C3 . H31 . 113.9(20) yes C11 . C3 . H31 . 120.9(20) yes C3 . C4 . C5 . 119.9(2) yes C3 . C4 . C11 . 60.62(18) yes C5 . C4 . C11 . 111.0(2) yes C3 . C4 . H41 . 113.7(17) yes C5 . C4 . H41 . 120.7(17) yes C11 . C4 . H41 . 116.1(18) yes C4 . C5 . C6 . 112.3(2) yes C4 . C5 . C9 . 104.20(19) yes C6 . C5 . C9 . 105.71(18) yes C4 . C5 . H51 . 110.07(14) no C6 . C5 . H51 . 109.16(15) no C9 . C5 . H51 . 115.39(13) no C5 . C6 . C7 . 106.68(19) yes C5 . C6 . H61 . 109.81(16) no C7 . C6 . H61 . 110.10(15) no C5 . C6 . H62 . 110.51(14) no C7 . C6 . H62 . 110.25(13) no H61 . C6 . H62 . 109.466 no C6 . C7 . C8 . 100.47(17) yes C6 . C7 . C20 . 112.5(2) yes C8 . C7 . C20 . 112.6(2) yes C6 . C7 . C21 . 110.5(2) yes C8 . C7 . C21 . 111.3(2) yes C20 . C7 . C21 . 109.3(2) yes C7 . C8 . C9 . 104.99(17) yes C7 . C8 . H81 . 110.74(13) no C9 . C8 . H81 . 110.59(12) no C7 . C8 . H82 . 110.56(12) no C9 . C8 . H82 . 110.43(11) no H81 . C8 . H82 . 109.467 no C5 . C9 . C8 . 103.30(17) yes C5 . C9 . C10 . 106.83(17) yes C8 . C9 . C10 . 116.32(18) yes C5 . C9 . H91 . 117.00(13) no C8 . C9 . H91 . 108.71(12) no C10 . C9 . H91 . 105.17(11) no C1 . C10 . C9 . 109.81(18) yes C1 . C10 . C11 . 102.50(19) yes C9 . C10 . C11 . 104.24(17) yes C1 . C10 . C22 . 110.93(19) yes C9 . C10 . C22 . 113.97(18) yes C11 . C10 . C22 . 114.6(2) yes C3 . C11 . C4 . 60.93(18) yes C3 . C11 . C10 . 106.5(2) yes C4 . C11 . C10 . 106.2(2) yes C3 . C11 . H111 . 121.6(16) yes C4 . C11 . H111 . 127.7(16) yes C10 . C11 . H111 . 119.4(16) yes O12 . C13 . O14 . 112.0(2) yes O12 . C13 . H131 . 108.70(13) no O14 . C13 . H131 . 107.94(12) no O12 . C13 . H132 . 109.49(12) no O14 . C13 . H132 . 109.18(13) no H131 . C13 . H132 . 109.467 no O14 . C15 . C16 . 109.4(2) yes O14 . C15 . H151 . 109.58(14) no C16 . C15 . H151 . 110.47(16) no O14 . C15 . H152 . 109.45(12) no C16 . C15 . H152 . 108.43(15) no H151 . C15 . H152 . 109.466 no O17 . C16 . C15 . 109.3(2) yes O17 . C16 . H161 . 109.90(13) no C15 . C16 . H161 . 108.69(14) no O17 . C16 . H162 . 109.54(14) no C15 . C16 . H162 . 109.89(15) no H161 . C16 . H162 . 109.467 no O17 . C17 . H171 . 108.50(16) no O17 . C17 . H172 . 110.20(15) no H171 . C17 . H172 . 109.476 no O17 . C17 . H173 . 109.69(16) no H171 . C17 . H173 . 109.476 no H172 . C17 . H173 . 109.476 no C7 . C20 . H201 . 109.90(14) no C7 . C20 . H202 . 109.20(14) no H201 . C20 . H202 . 109.475 no C7 . C20 . H203 . 109.31(14) no H201 . C20 . H203 . 109.474 no H202 . C20 . H203 . 109.475 no C7 . C21 . H211 . 109.92(16) no C7 . C21 . H212 . 109.73(14) no H211 . C21 . H212 . 109.476 no C7 . C21 . H213 . 108.75(15) no H211 . C21 . H213 . 109.476 no H212 . C21 . H213 . 109.476 no C10 . C22 . H221 . 110.17(13) no C10 . C22 . H222 . 108.96(13) no H221 . C22 . H222 . 109.476 no C10 . C22 . H223 . 109.26(14) no H221 . C22 . H223 . 109.476 no H222 . C22 . H223 . 109.476 no