# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_CRYSTALS_cif _database_code_CSD 190887 _audit_creation_date 00-11-02 _audit_creation_method CRYSTALS_ver_12-03-99 # ES15 # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; ? ; _publ_contact_author_name 'Prof Stephen G Davies' _publ_contact_author_address ; Prof Stephen G Davies The Dyson Perrins Laboratory University of Oxford South Parks Road Oxford OX1 3QY UNITED KINGDOM ; _publ_contact_author_email ' STEVE.DAVIES@CHEM.OXFORD.AC.UK ' _publ_requested_journal 'Chemical Communications' #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_Cambridge 182 _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Double Diastereoselective [3,3]-sigmatropic aza-claisen rearrangements. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name 'Stephen G. Davies' 'A. Christopher Garner' 'Rebecca L. Nicholson' 'James Osborne' 'Edward D. Savory' 'Andrew D. Smith' #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; ? ; _publ_section_comment #Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; ## -----------------REFERENCES ----------------------## _publ_section_references # Add your own references - in alphabetic order ; # SIR92 # 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 # Chebychev Weights # Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 # Denzo # 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. # Extinction correction # Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294 # Azimutal absorption correction # North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 # SHELXS 86 # Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. # DIFABS # Walker, N., and Stuart, D. Acta Cryst, (1983) A39, 158-166 # CRYSTALS # Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. #CAMERON # Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. # RC93 # Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; #========================================================================== # Diffractometer details #========================================================================== # choose from: #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ CAD4 _diffrn_measurement_device_type ' Enraf-nonius CAD4 ' _diffrn_radiation_monochromator graphite _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' # or #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ DIP 2000 _diffrn_measurement_device_type ; Enraf-nonius DIP2000 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DIP2000 software 'Xpress' (MAC Science, 1989) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; # or #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ STOE IPDS _diffrn_radiation_monochromator graphite _diffrn_measurement_device-type 'Stoe IPDS ' _computing_data_collection 'Stoe IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_cell_refinement 'Stoe IPDS software (Stoe, 1996)' # end_choice #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # choose one of the following two lines # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _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 #**************************************************************************** _cell_length_a 4.9041(8) _cell_angle_alpha 90 _cell_length_b 14.4817(15) _cell_angle_beta 90 _cell_length_c 31.335(7) _cell_angle_gamma 90 _cell_volume 2225.4 _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 ' 0.0170 0.0090 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 ' 0.0290 0.0180 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 ' 0.0470 0.0320 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 ' C24 H31 N1 O2 ' _chemical_formula_moiety ' C24 H31 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 365.52 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23 _cell_measurement_theta_max 43 _cell_measurement_temperature 293 _cell_formula_units_Z 4 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.80 _exptl_crystal_density_diffrn 1.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 794.02 _exptl_absorpt_coefficient_mu 0.53 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details 'refined from delta-F (Walker & Stuart , 1983)' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.90 # Sheldrick geometric definitions 0.90 0.90 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 3.50 _diffrn_ambient_temperature 293 _diffrn_reflns_number 2766 _reflns_number_total 2660 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 2660 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2270 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 2107 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 74.33 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 39 _reflns_limit_h_min 0 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 39 _refine_diff_density_min -0.15 _refine_diff_density_max 0.27 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2107 _refine_ls_number_parameters 245 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.0747 _refine_ls_goodness_of_fit_ref 0.9426 _refine_ls_shift/su_max 0.012442 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 6.99 4.82 4.54 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # 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 0.2858(4) 0.00304(18) 0.34582(8) 0.0749 1.0000 Uani C2 0.0973(5) -0.0616(2) 0.34122(9) 0.0716 1.0000 Uani O3 -0.1493(4) -0.04248(18) 0.3390(1) 0.1058 1.0000 Uani C4 0.1891(5) -0.1608(2) 0.33914(9) 0.0727 1.0000 Uani C5 0.1272(6) -0.2011(2) 0.2949(1) 0.0787 1.0000 Uani C6 0.2599(7) -0.1463(3) 0.26045(11) 0.0893 1.0000 Uani C7 0.1483(8) -0.0927(4) 0.23274(13) 0.1131 1.0000 Uani C8 0.281(1) -0.0354(3) 0.19823(13) 0.1145 1.0000 Uani C9 0.162(1) -0.0498(3) 0.15710(13) 0.1149 1.0000 Uani O10 0.2942(6) 0.0028(2) 0.12539(8) 0.1067 1.0000 Uani C11 0.1701(11) -0.0037(4) 0.08584(15) 0.1246 1.0000 Uani C12 0.3344(9) 0.0427(3) 0.05215(12) 0.0948 1.0000 Uani C13 0.3270(15) 0.0097(3) 0.01085(15) 0.1303 1.0000 Uani C14 0.4731(16) 0.0517(4) -0.02148(15) 0.1364 1.0000 Uani C15 0.6313(13) 0.1265(5) -0.01174(17) 0.1378 1.0000 Uani C16 0.6361(14) 0.1603(4) 0.02817(16) 0.1437 1.0000 Uani C17 0.4887(11) 0.1187(4) 0.06020(14) 0.1194 1.0000 Uani C18 0.2144(14) -0.3027(3) 0.29243(15) 0.1262 1.0000 Uani C19 0.0514(12) -0.2146(3) 0.37508(12) 0.1163 1.0000 Uani C20 0.2332(6) 0.1016(2) 0.34551(11) 0.0856 1.0000 Uani C21 0.3409(6) 0.1502(2) 0.3846(1) 0.0742 1.0000 Uani C22 0.525(1) 0.1128(2) 0.41168(12) 0.1018 1.0000 Uani C23 0.6290(13) 0.1623(3) 0.44581(14) 0.1227 1.0000 Uani C24 0.5460(11) 0.2490(3) 0.45366(15) 0.1149 1.0000 Uani C25 0.3673(15) 0.2872(3) 0.4277(2) 0.1632 1.0000 Uani C26 0.2636(12) 0.2386(3) 0.3934(2) 0.1448 1.0000 Uani C27 0.3491(15) 0.1435(4) 0.30432(15) 0.1391 1.0000 Uani H41 0.3913 -0.1662 0.3436 0.0809 1.0000 Uiso H51 -0.0753 -0.1980 0.2897 0.0900 1.0000 Uiso H61 0.4644 -0.1532 0.2585 0.0999 1.0000 Uiso H71 -0.0573 -0.0836 0.2350 0.1209 1.0000 Uiso H81 0.4799 -0.0518 0.1970 0.1286 1.0000 Uiso H82 0.2684 0.0331 0.2058 0.1286 1.0000 Uiso H91 0.1702 -0.1163 0.1497 0.1359 1.0000 Uiso H92 -0.0368 -0.0299 0.1581 0.1359 1.0000 Uiso H111 -0.0158 0.0272 0.0872 0.1442 1.0000 Uiso H112 0.1423 -0.0699 0.0778 0.1442 1.0000 Uiso H131 0.2158 -0.0484 0.0042 0.1456 1.0000 Uiso H141 0.4680 0.0263 -0.0516 0.1627 1.0000 Uiso H151 0.7481 0.1570 -0.0355 0.1605 1.0000 Uiso H161 0.7444 0.2194 0.0357 0.1679 1.0000 Uiso H171 0.4865 0.1482 0.0896 0.1402 1.0000 Uiso H181 0.1769 -0.3297 0.2635 0.1449 1.0000 Uiso H182 0.1190 -0.3406 0.3146 0.1449 1.0000 Uiso H183 0.4192 -0.3080 0.2978 0.1449 1.0000 Uiso H191 0.1080 -0.2812 0.3743 0.1321 1.0000 Uiso H192 0.0994 -0.1877 0.4034 0.1321 1.0000 Uiso H193 -0.1536 -0.2118 0.3714 0.1321 1.0000 Uiso H201 0.0285 0.1111 0.3453 0.0968 1.0000 Uiso H221 0.5898 0.0462 0.4071 0.1213 1.0000 Uiso H231 0.7668 0.1312 0.4662 0.1462 1.0000 Uiso H241 0.6221 0.2862 0.4781 0.1403 1.0000 Uiso H251 0.3015 0.3534 0.4328 0.1837 1.0000 Uiso H261 0.1309 0.2704 0.3735 0.1647 1.0000 Uiso H271 0.3149 0.2115 0.3032 0.1606 1.0000 Uiso H272 0.5538 0.1329 0.3035 0.1606 1.0000 Uiso H273 0.2673 0.1135 0.2785 0.1606 1.0000 Uiso H1 0.4269 -0.0204 0.3478 0.0500 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 0.0289(9) 0.0882(14) 0.1077(16) -0.0105(13) -0.007(1) 0.015(1) C2 0.031(1) 0.0964(18) 0.0874(17) -0.0096(15) -0.0018(11) 0.0143(12) O3 0.0269(8) 0.1086(16) 0.182(2) -0.0138(17) -0.0013(12) 0.016(1) C4 0.0394(11) 0.0935(17) 0.0851(16) -0.0078(14) -0.0065(12) 0.0135(13) C5 0.0473(14) 0.101(2) 0.0874(17) -0.0114(16) -0.0015(13) -0.0102(15) C6 0.0518(15) 0.123(3) 0.0928(19) -0.0107(19) 0.0044(15) -0.0042(19) C7 0.0601(19) 0.173(4) 0.106(2) 0.021(3) -0.0072(19) -0.017(2) C8 0.084(2) 0.149(4) 0.110(2) 0.011(2) -0.008(2) -0.023(3) C9 0.089(2) 0.140(3) 0.116(3) 0.006(3) 0.000(2) -0.023(3) O10 0.0938(18) 0.1247(18) 0.1014(16) 0.0102(14) -0.0043(15) -0.0232(17) C11 0.097(3) 0.149(4) 0.128(3) 0.009(3) -0.022(3) -0.021(3) C12 0.081(2) 0.099(2) 0.104(2) 0.0126(18) -0.018(2) 0.007(2) C13 0.180(6) 0.097(2) 0.113(3) -0.000(2) -0.029(4) -0.001(4) C14 0.178(6) 0.129(3) 0.102(3) 0.009(3) -0.010(4) 0.028(5) C15 0.121(4) 0.178(5) 0.115(3) 0.045(3) -0.009(3) 0.009(4) C16 0.142(5) 0.175(5) 0.114(3) 0.022(3) -0.024(3) -0.045(4) C17 0.107(3) 0.145(4) 0.106(2) -0.010(3) -0.020(3) -0.032(3) C18 0.144(4) 0.097(2) 0.138(3) -0.033(2) -0.001(4) -0.009(3) C19 0.121(4) 0.129(3) 0.099(2) 0.021(2) 0.014(2) 0.037(3) C20 0.0456(14) 0.0913(18) 0.120(2) 0.0073(18) -0.0153(17) 0.0141(14) C21 0.0426(12) 0.0719(15) 0.1082(19) 0.0030(15) 0.0085(13) 0.0038(13) C22 0.109(3) 0.0843(19) 0.112(2) -0.0150(18) -0.024(2) 0.025(2) C23 0.142(4) 0.107(3) 0.120(3) -0.021(2) -0.028(3) 0.018(3) C24 0.104(3) 0.101(3) 0.140(3) -0.032(2) 0.004(3) 0.007(3) C25 0.143(5) 0.096(3) 0.251(6) -0.064(4) -0.035(5) 0.042(3) C26 0.115(4) 0.102(3) 0.218(5) -0.028(3) -0.055(4) 0.050(3) C27 0.161(5) 0.139(4) 0.117(3) 0.029(3) -0.031(3) -0.004(4) _refine_ls_extinction_coef 195.1(153) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' 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 . C2 . 1.323(4) yes N1 . C20 . 1.451(4) yes N1 . H1 . 0.7731(19) no C2 . O3 . 1.242(3) yes C2 . C4 . 1.508(4) yes C4 . C5 . 1.534(4) yes C4 . C19 . 1.526(5) yes C4 . H41 . 1.005(2) no C5 . C6 . 1.490(5) yes C5 . C18 . 1.534(6) yes C5 . H51 . 1.007(3) no C6 . C7 . 1.287(6) yes C6 . H61 . 1.010(3) no C7 . C8 . 1.510(6) yes C7 . H71 . 1.019(4) no C8 . C9 . 1.430(6) yes C8 . H81 . 1.006(5) no C8 . H82 . 1.023(5) no C9 . O10 . 1.411(5) yes C9 . H91 . 0.992(5) no C9 . H92 . 1.016(5) no O10 . C11 . 1.384(5) yes C11 . C12 . 1.489(6) yes C11 . H111 . 1.017(6) no C11 . H112 . 1.000(5) no C12 . C13 . 1.380(6) yes C12 . C17 . 1.359(6) yes C13 . C14 . 1.382(7) yes C13 . H131 . 1.024(5) no C14 . C15 . 1.368(8) yes C14 . H141 . 1.014(5) no C15 . C16 . 1.343(7) yes C15 . H151 . 1.037(6) no C16 . C17 . 1.376(7) yes C16 . H161 . 1.034(6) no C17 . H171 . 1.016(4) no C18 . H181 . 1.003(4) no C18 . H182 . 1.001(5) no C18 . H183 . 1.022(7) no C19 . H191 . 1.005(4) no C19 . H192 . 0.998(5) no C19 . H193 . 1.013(6) no C20 . C21 . 1.507(5) yes C20 . C27 . 1.535(6) yes C20 . H201 . 1.013(3) no C21 . C22 . 1.353(5) yes C21 . C26 . 1.364(5) yes C22 . C23 . 1.385(5) yes C22 . H221 . 1.025(3) no C23 . C24 . 1.344(6) yes C23 . H231 . 1.033(5) no C24 . C25 . 1.317(8) yes C24 . H241 . 1.008(4) no C25 . C26 . 1.381(7) yes C25 . H251 . 1.024(4) no C26 . H261 . 1.011(5) no C27 . H271 . 0.999(5) no C27 . H272 . 1.016(7) no C27 . H273 . 1.002(5) 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 C2 . N1 . C20 . 124.8(2) yes C2 . N1 . H1 . 108.9(3) no C20 . N1 . H1 . 126.3(3) no N1 . C2 . O3 . 121.9(3) yes N1 . C2 . C4 . 118.0(2) yes O3 . C2 . C4 . 120.0(3) yes C2 . C4 . C5 . 110.0(2) yes C2 . C4 . C19 . 108.8(3) yes C5 . C4 . C19 . 112.7(3) yes C2 . C4 . H41 . 111.3(3) no C5 . C4 . H41 . 106.9(2) no C19 . C4 . H41 . 107.2(3) no C4 . C5 . C6 . 111.4(3) yes C4 . C5 . C18 . 110.8(3) yes C6 . C5 . C18 . 110.7(3) yes C4 . C5 . H51 . 108.9(3) no C6 . C5 . H51 . 106.8(3) no C18 . C5 . H51 . 108.0(3) no C5 . C6 . C7 . 128.7(3) yes C5 . C6 . H61 . 115.1(3) no C7 . C6 . H61 . 116.2(3) no C6 . C7 . C8 . 129.2(4) yes C6 . C7 . H71 . 116.8(4) no C8 . C7 . H71 . 113.9(4) no C7 . C8 . C9 . 113.0(4) yes C7 . C8 . H81 . 108.4(4) no C9 . C8 . H81 . 109.2(4) no C7 . C8 . H82 . 109.9(4) no C9 . C8 . H82 . 109.1(4) no H81 . C8 . H82 . 107.2(4) no C8 . C9 . O10 . 111.6(4) yes C8 . C9 . H91 . 109.6(4) no O10 . C9 . H91 . 109.9(4) no C8 . C9 . H92 . 108.9(4) no O10 . C9 . H92 . 108.0(4) no H91 . C9 . H92 . 108.8(4) no C9 . O10 . C11 . 113.0(3) yes O10 . C11 . C12 . 111.5(4) yes O10 . C11 . H111 . 109.0(4) no C12 . C11 . H111 . 108.4(4) no O10 . C11 . H112 . 110.6(4) no C12 . C11 . H112 . 109.2(4) no H111 . C11 . H112 . 108.1(5) no C11 . C12 . C13 . 119.6(4) yes C11 . C12 . C17 . 122.4(4) yes C13 . C12 . C17 . 118.0(4) yes C12 . C13 . C14 . 121.4(5) yes C12 . C13 . H131 . 119.3(5) no C14 . C13 . H131 . 119.2(5) no C13 . C14 . C15 . 118.6(5) yes C13 . C14 . H141 . 120.7(7) no C15 . C14 . H141 . 120.6(7) no C14 . C15 . C16 . 120.4(5) yes C14 . C15 . H151 . 119.4(6) no C16 . C15 . H151 . 120.2(7) no C15 . C16 . C17 . 120.7(5) yes C15 . C16 . H161 . 121.6(6) no C17 . C16 . H161 . 117.7(5) no C12 . C17 . C16 . 120.8(4) yes C12 . C17 . H171 . 120.2(5) no C16 . C17 . H171 . 118.9(5) no C5 . C18 . H181 . 111.6(4) no C5 . C18 . H182 . 111.1(4) no H181 . C18 . H182 . 109.1(4) no C5 . C18 . H183 . 109.7(4) no H181 . C18 . H183 . 107.5(5) no H182 . C18 . H183 . 107.7(5) no C4 . C19 . H191 . 110.5(4) no C4 . C19 . H192 . 110.7(5) no H191 . C19 . H192 . 109.3(4) no C4 . C19 . H193 . 109.6(3) no H191 . C19 . H193 . 108.1(5) no H192 . C19 . H193 . 108.6(4) no N1 . C20 . C21 . 113.0(3) yes N1 . C20 . C27 . 109.2(3) yes C21 . C20 . C27 . 111.6(3) yes N1 . C20 . H201 . 108.0(3) no C21 . C20 . H201 . 106.9(3) no C27 . C20 . H201 . 107.8(3) no C20 . C21 . C22 . 123.9(3) yes C20 . C21 . C26 . 120.3(3) yes C22 . C21 . C26 . 115.7(3) yes C21 . C22 . C23 . 121.5(3) yes C21 . C22 . H221 . 119.7(3) no C23 . C22 . H221 . 118.8(4) no C22 . C23 . C24 . 120.9(5) yes C22 . C23 . H231 . 119.5(4) no C24 . C23 . H231 . 119.5(4) no C23 . C24 . C25 . 118.8(5) yes C23 . C24 . H241 . 121.7(5) no C25 . C24 . H241 . 119.5(5) no C24 . C25 . C26 . 120.8(4) yes C24 . C25 . H251 . 120.3(6) no C26 . C25 . H251 . 118.9(6) no C21 . C26 . C25 . 122.2(4) yes C21 . C26 . H261 . 118.8(5) no C25 . C26 . H261 . 118.9(4) no C20 . C27 . H271 . 110.9(5) no C20 . C27 . H272 . 109.1(4) no H271 . C27 . H272 . 108.3(6) no C20 . C27 . H273 . 111.0(5) no H271 . C27 . H273 . 109.4(5) no H272 . C27 . H273 . 108.1(6) no