# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_CRYSTALS_cif _database_code_CSD 187479 _audit_creation_date 01-12-10 _audit_creation_method CRYSTALS_ver_12-03-99 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Davies, Stephen G.' 'Bull, Steven D.' 'Garner, A. Christopher' ; O'Shea, Michael D. ; 'Savory, Edward D.' 'Snow, Emma J.' _publ_contact_author_name 'Prof Stephen G Davies' _publ_contact_author_address ; The Dyson Perrins Laboratory University of Oxford South Parks Road Oxford OX1 3QY UNITED KINGDOM ; _publ_contact_author_email 'STEVE.DAVIES@CHEMISTRY.OX.AC.UK' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines ; _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et all 2001) ; _computing_publication_material ; CRYSTALS (Watkin et all 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 7.4482(1) _cell_angle_alpha 90 _cell_length_b 10.8159(2) _cell_angle_beta 90 _cell_length_c 29.5153(4) _cell_angle_gamma 90 _cell_volume 2377.7 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,-y+1/2,-z' '-x,y+1/2,-z+1/2' '-x+1/2,-y,z+1/2' 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 ' C25 H30 N2 O6 ' _chemical_formula_moiety ' C25 H30 N2 O6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 454.52 _cell_measurement_reflns_used 2961 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 968.280 _exptl_absorpt_coefficient_mu 0.091 # Sheldrick geometric definitions 0.96 0.96 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 5227 _reflns_number_total 3044 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3044 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2732 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 2646 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _reflns_limit_h_min 0 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 38 _refine_diff_density_min -0.16 _refine_diff_density_max 0.18 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2646 _refine_ls_number_parameters 298 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0201 _refine_ls_goodness_of_fit_ref 1.0654 _refine_ls_shift/su_max 0.000796 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 0.681 -.781 0.267 -.395 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. 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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.84175(14) 0.1855(1) 0.91122(4) 0.0382 1.0000 Uani C2 0.7130(2) 0.18378(14) 0.88552(5) 0.0298 1.0000 Uani N3 0.72364(17) 0.22601(12) 0.84222(4) 0.0316 1.0000 Uani C4 0.5811(2) 0.21728(15) 0.80988(5) 0.0320 1.0000 Uani O5 0.63838(16) 0.1322(1) 0.77470(3) 0.0368 1.0000 Uani C6 0.6377(3) 0.17382(18) 0.73123(5) 0.0419 1.0000 Uani O7 0.6114(3) 0.27958(14) 0.72164(4) 0.0677 1.0000 Uani C8 0.6705(3) 0.0710(2) 0.69888(6) 0.0514 1.0000 Uani C9 0.4063(2) 0.16067(15) 0.82625(5) 0.0329 1.0000 Uani O10 0.28066(17) 0.15726(14) 0.79961(4) 0.0499 1.0000 Uani N11 0.40411(17) 0.10808(12) 0.86766(4) 0.0306 1.0000 Uani C12 0.5327(2) 0.14131(14) 0.90305(5) 0.0292 1.0000 Uani C13 0.4498(2) 0.24011(17) 0.93517(5) 0.0397 1.0000 Uani C14 0.4205(3) 0.36332(18) 0.91119(8) 0.0591 1.0000 Uani C15 0.5567(3) 0.2550(3) 0.97894(6) 0.0645 1.0000 Uani C16 0.2413(2) 0.03982(16) 0.88141(5) 0.0385 1.0000 Uani C17 0.2837(2) -0.07081(15) 0.91065(5) 0.0339 1.0000 Uani C18 0.2288(2) -0.07501(15) 0.95559(6) 0.0392 1.0000 Uani C19 0.2519(2) -0.18057(16) 0.98185(5) 0.0389 1.0000 Uani C20 0.3328(2) -0.28333(14) 0.96314(5) 0.0346 1.0000 Uani O21 0.35681(18) -0.3937(1) 0.98494(4) 0.0420 1.0000 Uani C22 0.2837(3) -0.40374(18) 1.02966(6) 0.0510 1.0000 Uani C23 0.3965(3) -0.27863(16) 0.91858(5) 0.0427 1.0000 Uani C24 0.3709(3) -0.17406(16) 0.89275(5) 0.0425 1.0000 Uani C25 0.8910(2) 0.28650(16) 0.82654(5) 0.0372 1.0000 Uani C26 0.8870(2) 0.42443(15) 0.83364(5) 0.0338 1.0000 Uani C27 0.8394(2) 0.50425(16) 0.79877(5) 0.0375 1.0000 Uani C28 0.8344(2) 0.63234(16) 0.80504(6) 0.0388 1.0000 Uani C29 0.8786(2) 0.68071(16) 0.84696(6) 0.0408 1.0000 Uani O30 0.8798(2) 0.80434(12) 0.85694(5) 0.0550 1.0000 Uani C31 0.8372(3) 0.88814(18) 0.82146(8) 0.0610 1.0000 Uani C32 0.9272(3) 0.60259(17) 0.88230(6) 0.0440 1.0000 Uani C33 0.9308(2) 0.47617(17) 0.87575(5) 0.0404 1.0000 Uani H41 0.5564 0.3056 0.8001 0.0405 1.0000 Uiso H81 0.6703 0.0980 0.6672 0.0666 1.0000 Uiso H82 0.7903 0.0308 0.7063 0.0666 1.0000 Uiso H83 0.5747 0.0045 0.7033 0.0666 1.0000 Uiso H121 0.5591 0.0639 0.9208 0.0358 1.0000 Uiso H131 0.3285 0.2079 0.9444 0.0511 1.0000 Uiso H141 0.3694 0.4251 0.9329 0.0790 1.0000 Uiso H142 0.5419 0.3958 0.9005 0.0790 1.0000 Uiso H143 0.3409 0.3529 0.8849 0.0790 1.0000 Uiso H151 0.4986 0.3177 0.9993 0.0845 1.0000 Uiso H152 0.5602 0.1730 0.9962 0.0845 1.0000 Uiso H153 0.6826 0.2803 0.9725 0.0845 1.0000 Uiso H161 0.1602 0.0968 0.8984 0.0487 1.0000 Uiso H162 0.1778 0.0099 0.8534 0.0487 1.0000 Uiso H181 0.1689 0.0006 0.9685 0.0484 1.0000 Uiso H191 0.2103 -0.1827 1.0139 0.0497 1.0000 Uiso H221 0.3121 -0.4867 1.0431 0.0693 1.0000 Uiso H222 0.3456 -0.3388 1.0504 0.0693 1.0000 Uiso H223 0.1540 -0.3879 1.0304 0.0693 1.0000 Uiso H231 0.4630 -0.3514 0.9060 0.0511 1.0000 Uiso H241 0.4163 -0.1719 0.8603 0.0549 1.0000 Uiso H251 0.9955 0.2509 0.8440 0.0492 1.0000 Uiso H252 0.9075 0.2683 0.7937 0.0492 1.0000 Uiso H271 0.8071 0.4685 0.7685 0.0470 1.0000 Uiso H281 0.7979 0.6888 0.7793 0.0492 1.0000 Uiso H311 0.8421 0.9758 0.8329 0.0772 1.0000 Uiso H312 0.9272 0.8793 0.7962 0.0772 1.0000 Uiso H313 0.7146 0.8711 0.8094 0.0772 1.0000 Uiso H321 0.9585 0.6382 0.9131 0.0528 1.0000 Uiso H331 0.9652 0.4195 0.9016 0.0501 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 O1 0.0323(6) 0.0445(6) 0.0379(5) 0.0058(5) -0.0044(5) 0.0009(5) C2 0.0320(7) 0.0269(7) 0.0306(7) 0.0019(6) 0.0007(6) 0.0036(6) N3 0.0320(6) 0.0321(6) 0.0306(6) 0.0027(5) 0.0039(5) 0.0013(6) C4 0.0381(8) 0.0307(7) 0.0271(6) 0.0018(6) 0.0029(6) 0.0060(7) O5 0.0451(6) 0.0379(6) 0.0275(5) -0.0001(4) 0.0054(5) 0.0091(6) C6 0.0442(9) 0.053(1) 0.0282(7) 0.0014(7) 0.0046(7) -0.0009(9) O7 0.1167(14) 0.0555(8) 0.0309(6) 0.0117(6) 0.0037(8) 0.003(1) C8 0.048(1) 0.0686(12) 0.0373(9) -0.0112(9) 0.0082(8) 0.001(1) C9 0.0352(7) 0.0377(8) 0.0259(6) 0.0022(6) -0.0005(6) 0.0062(7) O10 0.0391(6) 0.0783(9) 0.0323(5) 0.0122(6) -0.0076(5) 0.0009(7) N11 0.0302(6) 0.0337(6) 0.0279(6) 0.0053(5) -0.0026(5) 0.0006(6) C12 0.0314(7) 0.0318(7) 0.0244(6) 0.0045(6) -0.0023(6) 0.0006(6) C13 0.0375(8) 0.047(1) 0.0347(8) -0.0074(7) 0.0073(7) -0.0018(8) C14 0.0678(13) 0.042(1) 0.0677(12) -0.011(1) 0.0179(12) 0.010(1) C15 0.0586(12) 0.0967(17) 0.0382(9) -0.0279(11) 0.0006(9) -0.0013(13) C16 0.0317(8) 0.0440(9) 0.0398(8) 0.0100(7) -0.0038(7) -0.0037(8) C17 0.0307(7) 0.0363(8) 0.0347(7) 0.0039(7) -0.0024(6) -0.0059(7) C18 0.0375(8) 0.0382(8) 0.0420(8) 0.0018(7) 0.0096(7) 0.0018(7) C19 0.0411(9) 0.0412(9) 0.0344(7) 0.0046(7) 0.0089(7) 0.0000(8) C20 0.0360(8) 0.0323(7) 0.0355(7) 0.0034(6) -0.0015(7) -0.0079(7) O21 0.0521(7) 0.0335(6) 0.0403(6) 0.0056(5) 0.0026(6) -0.0018(6) C22 0.052(1) 0.049(1) 0.052(1) 0.0224(9) 0.0135(9) 0.0042(9) C23 0.0575(11) 0.0344(8) 0.0363(7) -0.0046(7) 0.0051(8) -0.0006(8) C24 0.0568(11) 0.0412(9) 0.0293(7) -0.0027(7) 0.0029(8) -0.0054(9) C25 0.0336(8) 0.0392(8) 0.0390(7) 0.0052(7) 0.0075(7) 0.0023(7) C26 0.0295(7) 0.0373(8) 0.0346(7) 0.0045(6) 0.0028(7) -0.0013(7) C27 0.0371(8) 0.0422(8) 0.0333(7) 0.0025(7) -0.0026(7) -0.0033(8) C28 0.0383(8) 0.0393(8) 0.0389(8) 0.0042(7) -0.0043(7) 0.0000(8) C29 0.0375(8) 0.0390(9) 0.0458(8) -0.0029(7) -0.0019(8) 0.0010(8) O30 0.0678(9) 0.0395(7) 0.0578(7) -0.0061(6) -0.0098(8) 0.0028(7) C31 0.0662(14) 0.0369(9) 0.0798(15) 0.004(1) -0.0140(12) 0.002(1) C32 0.048(1) 0.049(1) 0.0353(8) -0.0039(8) -0.0038(8) -0.0040(9) C33 0.0401(9) 0.0467(9) 0.0345(8) 0.0068(7) -0.0017(7) 0.0001(8) _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 O1 . C2 . 1.2226(17) yes C2 . N3 . 1.3596(18) yes C2 . C12 . 1.511(2) yes N3 . C4 . 1.4306(19) yes N3 . C25 . 1.482(2) yes C4 . O5 . 1.4516(17) yes C4 . C9 . 1.518(2) yes C4 . H41 . 1.0141(15) no O5 . C6 . 1.3598(18) yes C6 . O7 . 1.195(2) yes C6 . C8 . 1.486(3) yes C8 . H81 . 0.9811(19) no C8 . H82 . 1.017(2) no C8 . H83 . 1.021(2) no C9 . O10 . 1.2229(18) yes C9 . N11 . 1.3482(18) yes N11 . C12 . 1.4619(18) yes N11 . C16 . 1.476(2) yes C12 . C13 . 1.556(2) yes C12 . H121 . 1.0068(15) no C13 . C14 . 1.525(3) yes C13 . C15 . 1.526(2) yes C13 . H131 . 1.0053(17) no C14 . H141 . 1.0016(19) no C14 . H142 . 1.020(2) no C14 . H143 . 0.983(2) no C15 . H151 . 1.004(2) no C15 . H152 . 1.022(3) no C15 . H153 . 0.996(2) no C16 . C17 . 1.509(2) yes C16 . H161 . 0.9986(18) no C16 . H162 . 1.0065(17) no C17 . C18 . 1.389(2) yes C17 . C24 . 1.396(2) yes C18 . C19 . 1.391(2) yes C18 . H181 . 1.0069(16) no C19 . C20 . 1.380(2) yes C19 . H191 . 0.9968(15) no C20 . O21 . 1.3678(18) yes C20 . C23 . 1.399(2) yes O21 . C22 . 1.432(2) yes C22 . H221 . 1.0030(18) no C22 . H222 . 1.040(2) no C22 . H223 . 0.982(2) no C23 . C24 . 1.377(2) yes C23 . H231 . 1.0014(17) no C24 . H241 . 1.0146(16) no C25 . C26 . 1.507(2) yes C25 . H251 . 1.0098(17) no C25 . H252 . 0.9954(16) no C26 . C27 . 1.389(2) yes C26 . C33 . 1.402(2) yes C27 . C28 . 1.398(2) yes C27 . H271 . 1.0023(16) no C28 . C29 . 1.383(2) yes C28 . H281 . 1.0111(17) no C29 . O30 . 1.369(2) yes C29 . C32 . 1.390(2) yes O30 . C31 . 1.421(2) yes C31 . H311 . 1.007(2) no C31 . H312 . 1.007(3) no C31 . H313 . 0.998(2) no C32 . C33 . 1.381(3) yes C32 . H321 . 1.0137(16) no C33 . H331 . 1.0115(17) 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 O1 . C2 . N3 . 122.17(14) yes O1 . C2 . C12 . 119.30(12) yes N3 . C2 . C12 . 118.40(13) yes C2 . N3 . C4 . 124.20(13) yes C2 . N3 . C25 . 119.39(13) yes C4 . N3 . C25 . 116.41(12) yes N3 . C4 . O5 . 107.53(12) yes N3 . C4 . C9 . 116.78(12) yes O5 . C4 . C9 . 102.93(12) yes N3 . C4 . H41 . 105.20(13) no O5 . C4 . H41 . 116.56(12) no C9 . C4 . H41 . 108.33(13) no C4 . O5 . C6 . 117.63(13) yes O5 . C6 . O7 . 122.78(16) yes O5 . C6 . C8 . 110.96(16) yes O7 . C6 . C8 . 126.25(16) yes C6 . C8 . H81 . 113.0(2) no C6 . C8 . H82 . 108.98(17) no H81 . C8 . H82 . 109.61(17) no C6 . C8 . H83 . 109.30(16) no H81 . C8 . H83 . 109.29(19) no H82 . C8 . H83 . 106.5(2) no C4 . C9 . O10 . 117.65(13) yes C4 . C9 . N11 . 117.99(13) yes O10 . C9 . N11 . 124.10(15) yes C9 . N11 . C12 . 122.41(13) yes C9 . N11 . C16 . 118.05(12) yes C12 . N11 . C16 . 117.67(11) yes C2 . C12 . N11 . 114.35(11) yes C2 . C12 . C13 . 110.64(13) yes N11 . C12 . C13 . 110.14(13) yes C2 . C12 . H121 . 104.90(13) no N11 . C12 . H121 . 107.17(13) no C13 . C12 . H121 . 109.37(12) no C12 . C13 . C14 . 111.97(13) yes C12 . C13 . C15 . 112.41(15) yes C14 . C13 . C15 . 112.06(17) yes C12 . C13 . H131 . 106.43(14) no C14 . C13 . H131 . 107.41(17) no C15 . C13 . H131 . 106.08(15) no C13 . C14 . H141 . 109.88(18) no C13 . C14 . H142 . 108.53(19) no H141 . C14 . H142 . 107.76(19) no C13 . C14 . H143 . 110.65(17) no H141 . C14 . H143 . 110.7(2) no H142 . C14 . H143 . 109.2(2) no C13 . C15 . H151 . 110.7(2) no C13 . C15 . H152 . 110.08(19) no H151 . C15 . H152 . 107.45(18) no C13 . C15 . H153 . 110.98(16) no H151 . C15 . H153 . 109.5(2) no H152 . C15 . H153 . 108.0(2) no N11 . C16 . C17 . 112.47(13) yes N11 . C16 . H161 . 109.07(14) no C17 . C16 . H161 . 109.17(14) no N11 . C16 . H162 . 108.74(13) no C17 . C16 . H162 . 108.27(15) no H161 . C16 . H162 . 109.05(15) no C16 . C17 . C18 . 120.72(15) yes C16 . C17 . C24 . 121.01(14) yes C18 . C17 . C24 . 118.19(15) yes C17 . C18 . C19 . 121.51(15) yes C17 . C18 . H181 . 117.82(16) no C19 . C18 . H181 . 120.66(15) no C18 . C19 . C20 . 119.51(14) yes C18 . C19 . H191 . 120.64(16) no C20 . C19 . H191 . 119.84(16) no C19 . C20 . O21 . 124.87(14) yes C19 . C20 . C23 . 119.66(15) yes O21 . C20 . C23 . 115.46(15) yes C20 . O21 . C22 . 116.76(13) yes O21 . C22 . H221 . 110.57(17) no O21 . C22 . H222 . 108.86(15) no H221 . C22 . H222 . 106.15(18) no O21 . C22 . H223 . 112.51(17) no H221 . C22 . H223 . 110.74(18) no H222 . C22 . H223 . 107.76(19) no C20 . C23 . C24 . 120.24(16) yes C20 . C23 . H231 . 119.21(16) no C24 . C23 . H231 . 120.53(16) no C17 . C24 . C23 . 120.78(15) yes C17 . C24 . H241 . 119.57(16) no C23 . C24 . H241 . 119.65(17) no N3 . C25 . C26 . 112.13(13) yes N3 . C25 . H251 . 108.71(13) no C26 . C25 . H251 . 108.76(16) no N3 . C25 . H252 . 108.66(15) no C26 . C25 . H252 . 109.49(14) no H251 . C25 . H252 . 109.05(15) no C25 . C26 . C27 . 121.14(15) yes C25 . C26 . C33 . 120.94(15) yes C27 . C26 . C33 . 117.92(15) yes C26 . C27 . C28 . 121.63(15) yes C26 . C27 . H271 . 118.77(16) no C28 . C27 . H271 . 119.60(16) no C27 . C28 . C29 . 119.13(16) yes C27 . C28 . H281 . 120.38(16) no C29 . C28 . H281 . 120.48(16) no C28 . C29 . O30 . 124.29(16) yes C28 . C29 . C32 . 120.21(16) yes O30 . C29 . C32 . 115.49(16) yes C29 . O30 . C31 . 117.57(15) yes O30 . C31 . H311 . 110.2(2) no O30 . C31 . H312 . 109.67(18) no H311 . C31 . H312 . 108.3(2) no O30 . C31 . H313 . 110.53(19) no H311 . C31 . H313 . 109.1(2) no H312 . C31 . H313 . 109.1(2) no C29 . C32 . C33 . 120.12(16) yes C29 . C32 . H321 . 120.08(18) no C33 . C32 . H321 . 119.79(17) no C26 . C33 . C32 . 120.98(16) yes C26 . C33 . H331 . 119.03(17) no C32 . C33 . H331 . 119.99(17) no