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 _publ_contact_author_name 'Prof Stephen Davies' _publ_contact_author_address ; Chemistry University of Oxford Chemistry Research Laboratory Mansfield Rd Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Asymmetric Conjugate Reductions with Samarium Diiodide: Asymmetric Synthesis of (2S,3R)- and (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)-[2-2H,3-2H]-phenylalanine methyl ester. ; loop_ _publ_author_name 'Chris Garner' 'Carmen Concellon' 'Andrew Cowley' 'Chris Garner' 'Alistair G. Parkes' ; H.Rodriguez-Solla ; 'Andrew D. Smith' 'Juan A. Tamayo' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 260374' _audit_creation_date 01-11-10 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 13.3830(4) _cell_angle_alpha 90 _cell_length_b 7.0716(2) _cell_angle_beta 110.9299(15) _cell_length_c 13.9236(5) _cell_angle_gamma 90 _cell_volume 1230.8 _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 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 ' 0.0020 0.0020 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 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 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 _chemical_formula_sum ' C27 H34 N2 O4 ' _chemical_formula_moiety ' C27 H34 N2 O4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 450.58 _cell_measurement_reflns_used 14684 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_meas ? _exptl_crystal_F_000 484.115 _exptl_absorpt_coefficient_mu 0.081 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 14684 _reflns_number_total 2996 #3000 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.034 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_gt 2510 _diffrn_reflns_theta_min 5.26 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.15 _refine_diff_density_max 0.12 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2510 _refine_ls_number_parameters 298 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0354 _refine_ls_goodness_of_fit_ref 1.0513 _refine_ls_shift/su_max 0.004749 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.536 0.145 0.215 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _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 N1 0.12191(12) 0.3478(2) 0.38113(11) 0.0240 1.0000 Uani C1 0.19066(15) 0.3558(3) 0.32198(14) 0.0242 1.0000 Uani C2 0.13273(14) 0.3503(3) 0.20762(14) 0.0236 1.0000 Uani N2 0.04262(12) 0.2455(2) 0.17468(11) 0.0235 1.0000 Uani C3 0.00214(14) 0.1462(3) 0.24577(13) 0.0240 1.0000 Uani C4 0.02757(14) 0.2516(3) 0.34642(14) 0.0240 1.0000 Uani O1 0.16552(11) 0.4393(2) 0.1489(1) 0.0306 1.0000 Uani O2 -0.0338(1) 0.2454(2) 0.3942(1) 0.0300 1.0000 Uani C5 0.15318(16) 0.4454(3) 0.48077(14) 0.0269 1.0000 Uani C6 0.21911(15) 0.3284(3) 0.57235(14) 0.0252 1.0000 Uani C7 0.30326(16) 0.4128(3) 0.65115(15) 0.0300 1.0000 Uani C8 0.35915(16) 0.3148(3) 0.74041(15) 0.0323 1.0000 Uani C9 0.33186(15) 0.1283(3) 0.75190(15) 0.0293 1.0000 Uani C10 0.24945(15) 0.0404(3) 0.67407(15) 0.0293 1.0000 Uani C11 0.19396(15) 0.1413(3) 0.58503(14) 0.0276 1.0000 Uani O3 0.39196(12) 0.0450(2) 0.84369(11) 0.0387 1.0000 Uani C12 0.36522(19) -0.1450(4) 0.86061(18) 0.0417 1.0000 Uani C13 -0.02275(15) 0.2382(3) 0.06493(13) 0.0262 1.0000 Uani C14 -0.11377(15) 0.3783(3) 0.03483(13) 0.0236 1.0000 Uani C15 -0.19952(16) 0.3560(3) -0.05864(15) 0.0306 1.0000 Uani C16 -0.28128(17) 0.4877(3) -0.09044(15) 0.0337 1.0000 Uani C17 -0.27991(15) 0.6449(3) -0.02989(14) 0.0281 1.0000 Uani C18 -0.19653(15) 0.6687(3) 0.06313(14) 0.0279 1.0000 Uani C19 -0.11481(15) 0.5348(3) 0.09418(14) 0.0267 1.0000 Uani O4 -0.36429(11) 0.7677(2) -0.06829(11) 0.0347 1.0000 Uani C20 -0.35391(18) 0.9459(3) -0.01738(18) 0.0395 1.0000 Uani C21 0.29604(15) 0.3775(3) 0.36663(15) 0.0291 1.0000 Uani C22 0.37657(16) 0.3939(3) 0.31437(16) 0.0362 1.0000 Uani C23 0.4113(2) 0.5991(4) 0.3141(2) 0.0524 1.0000 Uani C24 0.4722(2) 0.2675(6) 0.3673(2) 0.0711 1.0000 Uani C25 0.03652(16) -0.0643(3) 0.25976(14) 0.0263 1.0000 Uani C26 0.15772(17) -0.0929(3) 0.30738(17) 0.0325 1.0000 Uani C27 -0.02093(17) -0.1698(3) 0.32050(15) 0.0321 1.0000 Uani H31 -0.0777 0.1444 0.2134 0.0298 1.0000 Uiso H51 0.0865 0.4857 0.4918 0.0337 1.0000 Uiso H52 0.1959 0.5596 0.4774 0.0337 1.0000 Uiso H71 0.3236 0.5464 0.6431 0.0373 1.0000 Uiso H81 0.4189 0.3777 0.7964 0.0382 1.0000 Uiso H101 0.2301 -0.0939 0.6818 0.0361 1.0000 Uiso H111 0.1346 0.0778 0.5289 0.0338 1.0000 Uiso H121 0.4143 -0.1891 0.9295 0.0505 1.0000 Uiso H122 0.2896 -0.1495 0.8581 0.0505 1.0000 Uiso H123 0.3730 -0.2291 0.8060 0.0505 1.0000 Uiso H131 0.0240 0.2663 0.0245 0.0317 1.0000 Uiso H132 -0.0531 0.1080 0.0480 0.0317 1.0000 Uiso H151 -0.2016 0.2436 -0.1028 0.0365 1.0000 Uiso H161 -0.3417 0.4698 -0.1574 0.0388 1.0000 Uiso H181 -0.1950 0.7806 0.1075 0.0336 1.0000 Uiso H191 -0.0550 0.5524 0.1615 0.0316 1.0000 Uiso H201 -0.4196 1.0233 -0.0516 0.0458 1.0000 Uiso H202 -0.3449 0.9250 0.0563 0.0458 1.0000 Uiso H203 -0.2900 1.0142 -0.0212 0.0458 1.0000 Uiso H211 0.3249 0.3836 0.4435 0.0360 1.0000 Uiso H221 0.3427 0.3513 0.2414 0.0453 1.0000 Uiso H231 0.4647 0.6082 0.2792 0.0664 1.0000 Uiso H232 0.4443 0.6452 0.3865 0.0664 1.0000 Uiso H233 0.3475 0.6787 0.2764 0.0664 1.0000 Uiso H241 0.5251 0.2795 0.3320 0.0901 1.0000 Uiso H242 0.5065 0.3066 0.4409 0.0901 1.0000 Uiso H243 0.4479 0.1331 0.3640 0.0901 1.0000 Uiso H251 0.0144 -0.1192 0.1890 0.0332 1.0000 Uiso H261 0.1742 -0.2313 0.3142 0.0408 1.0000 Uiso H262 0.1855 -0.0325 0.3769 0.0408 1.0000 Uiso H263 0.1926 -0.0336 0.2622 0.0408 1.0000 Uiso H271 0.0023 -0.3051 0.3287 0.0402 1.0000 Uiso H272 -0.0028 -0.1104 0.3898 0.0402 1.0000 Uiso H273 -0.1000 -0.1630 0.2828 0.0402 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 N1 0.0291(7) 0.0247(8) 0.0222(7) -0.0005(6) 0.0138(6) 0.0001(7) C1 0.0314(9) 0.0197(8) 0.0264(9) 0.0026(7) 0.0162(7) 0.0028(8) C2 0.0298(9) 0.0200(8) 0.0242(8) 0.0027(7) 0.0136(7) 0.0034(8) N2 0.0288(7) 0.0236(8) 0.0198(7) 0.0026(6) 0.0109(6) 0.0010(7) C3 0.0283(8) 0.0240(9) 0.0222(8) 0.0021(7) 0.0120(7) -0.0008(8) C4 0.0290(9) 0.0204(8) 0.0256(9) 0.0030(7) 0.0133(7) 0.0041(8) O1 0.0385(7) 0.0314(7) 0.0254(7) 0.0063(6) 0.0156(6) -0.0024(6) O2 0.0340(7) 0.0310(7) 0.0325(7) -0.0004(6) 0.0209(6) 0.0012(6) C5 0.037(1) 0.0228(9) 0.0244(9) -0.0016(8) 0.0153(7) 0.0003(8) C6 0.0308(9) 0.0251(9) 0.0240(9) -0.0009(7) 0.0150(7) 0.0013(8) C7 0.034(1) 0.028(1) 0.031(1) -0.0026(8) 0.0154(8) -0.0048(8) C8 0.0296(9) 0.0363(11) 0.030(1) -0.0008(9) 0.0089(8) -0.0025(9) C9 0.0278(9) 0.034(1) 0.029(1) 0.0045(8) 0.0141(8) 0.0056(9) C10 0.032(1) 0.0256(9) 0.033(1) 0.0008(8) 0.0145(8) 0.0017(8) C11 0.0324(9) 0.0249(9) 0.0273(9) -0.0025(8) 0.0129(8) 0.0002(8) O3 0.0352(8) 0.0417(9) 0.0353(8) 0.0116(7) 0.0079(6) 0.0047(7) C12 0.0465(12) 0.0381(12) 0.0415(12) 0.0123(11) 0.017(1) 0.0081(11) C13 0.0335(9) 0.0255(9) 0.0203(8) 0.0004(8) 0.0105(7) 0.0015(8) C14 0.0302(9) 0.0232(9) 0.0201(8) 0.0001(7) 0.0122(7) -0.0005(8) C15 0.038(1) 0.028(1) 0.0243(9) -0.0040(8) 0.0105(8) -0.0000(9) C16 0.0376(11) 0.0345(11) 0.0250(9) -0.0026(8) 0.0064(8) 0.0009(9) C17 0.0288(9) 0.029(1) 0.0280(9) 0.0042(8) 0.0116(8) 0.0039(8) C18 0.0332(9) 0.026(1) 0.0246(9) -0.0020(8) 0.0107(8) 0.0012(8) C19 0.0303(9) 0.0266(9) 0.0221(8) -0.0010(8) 0.0080(7) 0.0016(8) O4 0.0339(7) 0.0346(8) 0.0325(7) -0.0003(7) 0.0078(6) 0.0089(7) C20 0.0406(11) 0.0311(11) 0.0429(12) -0.000(1) 0.0100(9) 0.009(1) C21 0.0327(9) 0.031(1) 0.0266(9) 0.0017(8) 0.0140(8) 0.0004(8) C22 0.031(1) 0.0471(13) 0.0347(11) 0.0054(9) 0.0174(9) 0.003(1) C23 0.0452(13) 0.0609(18) 0.0598(16) 0.0034(13) 0.0293(12) -0.0138(13) C24 0.0494(14) 0.100(3) 0.0760(19) 0.035(2) 0.0368(15) 0.0346(18) C25 0.037(1) 0.0200(9) 0.0263(9) -0.0005(8) 0.0163(8) -0.0016(8) C26 0.0393(11) 0.023(1) 0.0396(11) 0.0030(8) 0.0197(9) 0.0066(8) C27 0.0456(11) 0.027(1) 0.0282(9) -0.0009(8) 0.0184(9) -0.0068(9) _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 N1 . C1 . 1.439(2) yes N1 . C4 . 1.362(2) yes N1 . C5 . 1.470(2) yes C1 . C2 . 1.502(3) yes C1 . C21 . 1.331(3) yes C2 . N2 . 1.348(2) yes C2 . O1 . 1.231(2) yes N2 . C3 . 1.466(2) yes N2 . C13 . 1.466(2) yes C3 . C4 . 1.515(3) yes C3 . C25 . 1.550(3) yes C3 . H31 . 1.0000 no C4 . O2 . 1.229(2) yes C5 . C6 . 1.512(3) yes C5 . H51 . 1.0000 no C5 . H52 . 1.000 no C6 . C7 . 1.395(3) yes C6 . C11 . 1.392(3) yes C7 . C8 . 1.386(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.393(3) yes C8 . H81 . 1.000 no C9 . C10 . 1.387(3) yes C9 . O3 . 1.376(2) yes C10 . C11 . 1.393(3) yes C10 . H101 . 1.000 no C11 . H111 . 1.000 no O3 . C12 . 1.432(3) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . C14 . 1.509(3) yes C13 . H131 . 1.0000 no C13 . H132 . 1.000 no C14 . C15 . 1.403(3) yes C14 . C19 . 1.384(3) yes C15 . C16 . 1.384(3) yes C15 . H151 . 1.000 no C16 . C17 . 1.391(3) yes C16 . H161 . 1.000 no C17 . C18 . 1.385(3) yes C17 . O4 . 1.373(2) yes C18 . C19 . 1.393(3) yes C18 . H181 . 1.0000 no C19 . H191 . 1.0000 no O4 . C20 . 1.428(3) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . C22 . 1.505(3) yes C21 . H211 . 1.0000 no C22 . C23 . 1.524(4) yes C22 . C24 . 1.518(4) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no C25 . C26 . 1.531(3) yes C25 . C27 . 1.526(3) yes C25 . H251 . 1.0000 no C26 . H261 . 1.000 no C26 . H262 . 1.000 no C26 . H263 . 1.000 no C27 . H271 . 1.000 no C27 . H272 . 1.000 no C27 . H273 . 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 . N1 . C4 . 121.21(15) yes C1 . N1 . C5 . 119.79(15) yes C4 . N1 . C5 . 118.99(14) yes N1 . C1 . C2 . 114.35(15) yes N1 . C1 . C21 . 121.65(16) yes C2 . C1 . C21 . 123.89(16) yes C1 . C2 . N2 . 115.80(15) yes C1 . C2 . O1 . 121.31(16) yes N2 . C2 . O1 . 122.88(17) yes C2 . N2 . C3 . 122.33(14) yes C2 . N2 . C13 . 120.14(15) yes C3 . N2 . C13 . 117.39(14) yes N2 . C3 . C4 . 111.94(16) yes N2 . C3 . C25 . 112.36(15) yes C4 . C3 . C25 . 113.44(15) yes N2 . C3 . H31 . 107.14 no C4 . C3 . H31 . 105.89 no C25 . C3 . H31 . 105.41 no N1 . C4 . C3 . 116.58(14) yes N1 . C4 . O2 . 122.69(17) yes C3 . C4 . O2 . 120.71(17) yes N1 . C5 . C6 . 114.99(16) yes N1 . C5 . H51 . 108.08 no C6 . C5 . H51 . 108.08 no N1 . C5 . H52 . 108.08 no C6 . C5 . H52 . 108.08 no H51 . C5 . H52 . 109.47 no C5 . C6 . C7 . 119.53(18) yes C5 . C6 . C11 . 122.18(18) yes C7 . C6 . C11 . 118.10(18) yes C6 . C7 . C8 . 121.10(19) yes C6 . C7 . H71 . 119.45 no C8 . C7 . H71 . 119.45 no C7 . C8 . C9 . 119.81(19) yes C7 . C8 . H81 . 120.1 no C9 . C8 . H81 . 120.1 no C8 . C9 . C10 . 120.17(18) yes C8 . C9 . O3 . 114.95(19) yes C10 . C9 . O3 . 124.89(19) yes C9 . C10 . C11 . 119.23(19) yes C9 . C10 . H101 . 120.38 no C11 . C10 . H101 . 120.38 no C6 . C11 . C10 . 121.58(19) yes C6 . C11 . H111 . 119.21 no C10 . C11 . H111 . 119.21 no C9 . O3 . C12 . 117.20(18) yes O3 . C12 . H121 . 109.5 no O3 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no O3 . C12 . H123 . 109.47 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no N2 . C13 . C14 . 112.87(15) yes N2 . C13 . H131 . 108.62 no C14 . C13 . H131 . 108.62 no N2 . C13 . H132 . 108.62 no C14 . C13 . H132 . 108.62 no H131 . C13 . H132 . 109.47 no C13 . C14 . C15 . 119.72(17) yes C13 . C14 . C19 . 122.58(16) yes C15 . C14 . C19 . 117.66(18) yes C14 . C15 . C16 . 120.84(18) yes C14 . C15 . H151 . 119.6 no C16 . C15 . H151 . 119.58 no C15 . C16 . C17 . 120.40(18) yes C15 . C16 . H161 . 119.8 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 119.70(18) yes C16 . C17 . O4 . 116.01(17) yes C18 . C17 . O4 . 124.28(18) yes C17 . C18 . C19 . 119.25(17) yes C17 . C18 . H181 . 120.38 no C19 . C18 . H181 . 120.38 no C14 . C19 . C18 . 122.15(17) yes C14 . C19 . H191 . 118.93 no C18 . C19 . H191 . 118.93 no C17 . O4 . C20 . 116.38(16) yes O4 . C20 . H201 . 109.47 no O4 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no O4 . C20 . H203 . 109.47 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C1 . C21 . C22 . 127.24(18) yes C1 . C21 . H211 . 116.38 no C22 . C21 . H211 . 116.38 no C21 . C22 . C23 . 110.23(19) yes C21 . C22 . C24 . 110.16(19) yes C23 . C22 . C24 . 110.9(2) yes C21 . C22 . H221 . 109.00 no C23 . C22 . H221 . 108.2 no C24 . C22 . H221 . 108.3 no C22 . C23 . H231 . 109.5 no C22 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C22 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C22 . C24 . H241 . 109.5 no C22 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no C22 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no C3 . C25 . C26 . 113.72(16) yes C3 . C25 . C27 . 110.71(16) yes C26 . C25 . C27 . 111.18(16) yes C3 . C25 . H251 . 106.20 no C26 . C25 . H251 . 105.67 no C27 . C25 . H251 . 109.02 no C25 . C26 . H261 . 109.47 no C25 . C26 . H262 . 109.47 no H261 . C26 . H262 . 109.5 no C25 . C26 . H263 . 109.47 no H261 . C26 . H263 . 109.48 no H262 . C26 . H263 . 109.5 no C25 . C27 . H271 . 109.47 no C25 . C27 . H272 . 109.47 no H271 . C27 . H272 . 109.48 no C25 . C27 . H273 . 109.47 no H271 . C27 . H273 . 109.48 no H272 . C27 . H273 . 109.48 no