data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Stephen G. Davies' _publ_contact_author_address ; Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Asymmetric Three and [2+1] Component Conjugate Addition Reactions for the Stereoselective Synthesis of Polysubstituted Piperidinones ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; ## -----------------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. ; loop_ _publ_author_name 'S. Davies' 'Paul M. Roberts' 'Andrew D. Smith' data_1 _database_code_depnum_ccdc_archive 'CCDC 634494' #========================================================================== # Diffractometer details #========================================================================== _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) ; #========================================================================== # 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 ? # 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 11.2640(2) _cell_angle_alpha 90 _cell_length_b 16.6340(3) _cell_angle_beta 90 _cell_length_c 17.0480(2) _cell_angle_gamma 90 _cell_volume 3194.2 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 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 'C38 H43 N1 O4' _chemical_formula_moiety 'C38 H43 N1 O4' _chemical_compound_source ? _chemical_formula_weight 577.76 _cell_measurement_reflns_used 12186 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27 _cell_measurement_temperature 100 _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 0.50 _exptl_crystal_density_diffrn 1.20 _exptl_crystal_F_000 1240.29 _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.97 # Sheldrick geometric definitions 0.97 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 100 _diffrn_reflns_number 3793 _reflns_number_total 3793 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 3793 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3409 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 3618 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.78 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.13 _refine_diff_density_max 0.18 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3618 _refine_ls_number_parameters 388 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0310 _refine_ls_goodness_of_fit_ref 0.9146 _refine_ls_shift/su_max 0.000523 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 2.43 0.858 1.59 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method \w # 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 1.14469(7) 0.16356(5) 0.37629(5) 0.0197 1.0000 Uani C2 1.2032(1) 0.11753(7) 0.32437(7) 0.0179 1.0000 Uani O3 1.27700(8) 0.06751(6) 0.34079(5) 0.0235 1.0000 Uani C4 1.1665(1) 0.13893(7) 0.24091(7) 0.0165 1.0000 Uani C5 1.2748(1) 0.16029(7) 0.18829(7) 0.0179 1.0000 Uani C6 1.3273(1) 0.24118(7) 0.21097(7) 0.0191 1.0000 Uani C7 1.28726(11) 0.30952(7) 0.17137(8) 0.0225 1.0000 Uani C8 1.33151(12) 0.38518(8) 0.18949(9) 0.0266 1.0000 Uani C9 1.41555(13) 0.39393(8) 0.24777(9) 0.0314 1.0000 Uani C10 1.45545(14) 0.32702(9) 0.28812(9) 0.0344 1.0000 Uani C11 1.41203(12) 0.25080(8) 0.26952(9) 0.0288 1.0000 Uani C12 1.36981(11) 0.09411(7) 0.18067(7) 0.0208 1.0000 Uani C13 1.44656(11) 0.11089(7) 0.10953(7) 0.0207 1.0000 Uani O14 1.56293(8) 0.10614(7) 0.12590(6) 0.0304 1.0000 Uani C15 1.64197(13) 0.12399(11) 0.06093(9) 0.0365 1.0000 Uani O16 1.40928(9) 0.12623(7) 0.04543(6) 0.0324 1.0000 Uani C17 1.0906(1) 0.07056(7) 0.20425(7) 0.0167 1.0000 Uani N18 0.99193(9) 0.04840(6) 0.25711(6) 0.0176 1.0000 Uani C19 0.94833(11) -0.03583(7) 0.24835(7) 0.0194 1.0000 Uani C20 1.04986(11) -0.09424(7) 0.26352(7) 0.0198 1.0000 Uani C21 1.09333(12) -0.10116(8) 0.33962(8) 0.0229 1.0000 Uani C22 1.18757(12) -0.15236(8) 0.35684(8) 0.0274 1.0000 Uani C23 1.24002(13) -0.19728(8) 0.29721(9) 0.0304 1.0000 Uani C24 1.19655(13) -0.19160(8) 0.22161(9) 0.0301 1.0000 Uani C25 1.10134(13) -0.14080(8) 0.20463(8) 0.0258 1.0000 Uani C26 0.87841(12) -0.05338(8) 0.17324(8) 0.0257 1.0000 Uani C27 0.89512(11) 0.10736(7) 0.25932(7) 0.0209 1.0000 Uani C28 0.80856(11) 0.09331(7) 0.32546(7) 0.0194 1.0000 Uani C29 0.68662(11) 0.09556(7) 0.31217(7) 0.0202 1.0000 Uani C30 0.60704(11) 0.08403(7) 0.37371(8) 0.0233 1.0000 Uani C31 0.64857(12) 0.07119(8) 0.44918(8) 0.0249 1.0000 Uani C32 0.77013(13) 0.07045(9) 0.46315(8) 0.0286 1.0000 Uani C33 0.84906(12) 0.08105(9) 0.40165(8) 0.0269 1.0000 Uani C34 1.0597(1) 0.09358(7) 0.11983(7) 0.0186 1.0000 Uani C35 1.09950(11) 0.04512(8) 0.05853(7) 0.0219 1.0000 Uani C36 1.08369(12) 0.06754(9) -0.01945(8) 0.0272 1.0000 Uani C37 1.02604(12) 0.1385(1) -0.03714(8) 0.0306 1.0000 Uani C38 0.98391(12) 0.18728(9) 0.02307(8) 0.0288 1.0000 Uani C39 1.00163(11) 0.16527(8) 0.10080(7) 0.0231 1.0000 Uani C40 1.17563(12) 0.16377(8) 0.46082(7) 0.0235 1.0000 Uani C41 1.15186(12) 0.08268(9) 0.49879(8) 0.0280 1.0000 Uani C42 1.09167(15) 0.22711(9) 0.49270(9) 0.0347 1.0000 Uani C43 1.30451(13) 0.18983(11) 0.47067(8) 0.0364 1.0000 Uani H41 1.1180 0.1884 0.2441 0.0151 1.0000 Uiso H51 1.2428 0.1664 0.1344 0.0156 1.0000 Uiso H71 1.2271 0.3053 0.1305 0.0330 1.0000 Uiso H81 1.3070 0.4318 0.1601 0.0387 1.0000 Uiso H91 1.4463 0.4464 0.2609 0.0353 1.0000 Uiso H101 1.5174 0.3333 0.3279 0.0403 1.0000 Uiso H111 1.4392 0.2034 0.2989 0.0327 1.0000 Uiso H121 1.4198 0.0893 0.2281 0.0233 1.0000 Uiso H122 1.3305 0.0413 0.1706 0.0233 1.0000 Uiso H151 1.7220 0.1130 0.0805 0.0440 1.0000 Uiso H152 1.6265 0.1797 0.0433 0.0440 1.0000 Uiso H153 1.6200 0.0887 0.0166 0.0440 1.0000 Uiso H171 1.1412 0.0216 0.2013 0.0190 1.0000 Uiso H191 0.8908 -0.0432 0.2927 0.0168 1.0000 Uiso H211 1.0576 -0.0692 0.3815 0.0308 1.0000 Uiso H221 1.2130 -0.1591 0.4120 0.0397 1.0000 Uiso H231 1.3082 -0.2329 0.3085 0.0348 1.0000 Uiso H241 1.2293 -0.2226 0.1783 0.0404 1.0000 Uiso H251 1.0731 -0.1377 0.1497 0.0247 1.0000 Uiso H261 0.8511 -0.1075 0.1737 0.0335 1.0000 Uiso H262 0.9296 -0.0466 0.1252 0.0335 1.0000 Uiso H263 0.8069 -0.0177 0.1703 0.0335 1.0000 Uiso H271 0.9306 0.1616 0.2664 0.0231 1.0000 Uiso H272 0.8499 0.1096 0.2076 0.0231 1.0000 Uiso H291 0.6575 0.1042 0.2576 0.0251 1.0000 Uiso H301 0.5181 0.0827 0.3634 0.0240 1.0000 Uiso H311 0.5947 0.0620 0.4929 0.0292 1.0000 Uiso H321 0.8007 0.0637 0.5170 0.0400 1.0000 Uiso H331 0.9371 0.0797 0.4107 0.0323 1.0000 Uiso H351 1.1374 -0.0053 0.0729 0.0218 1.0000 Uiso H361 1.1161 0.0330 -0.0635 0.0313 1.0000 Uiso H371 1.0128 0.1539 -0.0918 0.0384 1.0000 Uiso H381 0.9419 0.2378 0.0109 0.0366 1.0000 Uiso H391 0.9748 0.2007 0.1424 0.0277 1.0000 Uiso H411 1.1750 0.0858 0.5538 0.0380 1.0000 Uiso H412 1.1983 0.0400 0.4730 0.0380 1.0000 Uiso H413 1.0638 0.0691 0.4948 0.0380 1.0000 Uiso H421 1.1079 0.2336 0.5510 0.0440 1.0000 Uiso H422 1.1075 0.2771 0.4654 0.0440 1.0000 Uiso H423 1.0055 0.2085 0.4838 0.0440 1.0000 Uiso H431 1.3214 0.1975 0.5284 0.0494 1.0000 Uiso H432 1.3590 0.1486 0.4488 0.0494 1.0000 Uiso H433 1.3165 0.2394 0.4438 0.0494 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 0.0208(4) 0.0226(4) 0.0159(4) -0.0020(3) -0.0010(3) 0.0016(3) C2 0.0162(5) 0.0179(5) 0.0194(5) -0.0002(4) 0.0004(4) -0.0018(4) O3 0.0229(4) 0.0273(4) 0.0204(4) 0.0031(3) 0.0010(3) 0.0068(4) C4 0.0159(5) 0.0163(5) 0.0173(5) 0.0010(4) 0.0004(4) 0.0004(4) C5 0.0179(5) 0.0180(5) 0.0180(5) 0.0022(4) 0.0004(4) -0.0009(4) C6 0.0167(5) 0.0196(5) 0.0211(5) 0.0007(4) 0.0034(5) -0.0003(4) C7 0.0204(5) 0.0209(6) 0.0261(6) 0.0022(5) 0.0036(5) 0.0008(5) C8 0.0245(6) 0.0188(6) 0.0365(7) 0.0024(5) 0.0090(6) 0.0012(5) C9 0.0300(7) 0.0222(6) 0.0418(8) -0.0060(6) 0.0083(6) -0.0070(5) C10 0.0321(7) 0.0341(7) 0.0371(7) -0.0038(6) -0.0069(6) -0.0093(6) C11 0.0279(6) 0.0257(6) 0.0327(7) 0.0034(5) -0.0070(6) -0.0035(5) C12 0.0197(5) 0.0200(5) 0.0226(6) 0.0026(4) 0.0040(5) 0.0016(4) C13 0.0213(5) 0.0185(5) 0.0223(6) -0.0005(4) 0.0024(5) -0.0005(5) O14 0.0197(4) 0.0469(6) 0.0247(5) 0.0050(4) 0.0043(4) 0.0048(4) C15 0.0240(6) 0.0551(9) 0.0305(7) 0.0077(7) 0.0102(6) 0.0042(7) O16 0.0264(5) 0.0492(6) 0.0215(5) 0.0045(4) -0.0000(4) -0.0037(5) C17 0.0164(5) 0.0173(5) 0.0165(5) 0.0007(4) 0.0009(4) 0.0007(4) N18 0.0161(4) 0.0171(4) 0.0197(4) 0.0008(4) 0.0017(4) -0.0008(4) C19 0.0188(5) 0.0191(5) 0.0203(5) -0.0000(4) 0.0012(5) -0.0040(4) C20 0.0215(5) 0.0155(5) 0.0222(6) 0.0007(4) 0.0022(5) -0.0041(4) C21 0.0240(6) 0.0215(5) 0.0233(6) -0.0002(5) 0.0001(5) -0.0029(5) C22 0.0265(6) 0.0240(6) 0.0316(7) 0.0048(5) -0.0049(5) -0.0032(5) C23 0.0272(6) 0.0218(6) 0.0422(8) 0.0057(6) 0.0034(6) 0.0013(5) C24 0.0362(7) 0.0203(6) 0.0337(7) -0.0003(5) 0.0104(6) 0.0026(6) C25 0.0345(7) 0.0198(6) 0.0232(6) 0.0001(5) 0.0043(5) -0.0022(5) C26 0.0244(6) 0.0294(6) 0.0233(6) -0.0015(5) -0.0026(5) -0.0059(5) C27 0.0188(5) 0.0217(6) 0.0221(6) 0.0029(5) 0.0031(5) 0.0011(5) C28 0.0201(5) 0.0169(5) 0.0211(5) -0.0002(4) 0.0027(5) 0.0002(4) C29 0.0212(6) 0.0172(5) 0.0224(6) 0.0008(4) 0.0014(5) 0.0012(4) C30 0.0211(6) 0.0204(6) 0.0284(6) 0.0003(5) 0.0049(5) 0.0014(5) C31 0.0284(6) 0.0235(6) 0.0227(6) -0.0020(5) 0.0098(5) -0.0016(5) C32 0.0344(7) 0.0341(7) 0.0175(6) -0.0016(5) 0.0001(5) -0.0022(6) C33 0.0228(6) 0.0346(7) 0.0233(6) -0.0012(5) -0.0015(5) -0.0026(5) C34 0.0150(5) 0.0226(6) 0.0182(5) 0.0019(4) -0.0002(4) -0.0028(4) C35 0.0191(5) 0.0258(6) 0.0209(6) -0.0027(5) 0.0012(5) -0.0046(5) C36 0.0236(6) 0.0380(7) 0.0201(6) -0.0035(5) 0.0011(5) -0.0081(6) C37 0.0238(6) 0.0492(8) 0.0187(6) 0.0078(6) -0.0032(5) -0.0070(6) C38 0.0204(6) 0.0385(7) 0.0274(6) 0.0111(6) -0.0015(5) 0.0002(6) C39 0.0194(5) 0.0270(6) 0.0230(6) 0.0046(5) 0.0014(5) 0.0018(5) C40 0.0229(6) 0.0315(6) 0.0162(5) -0.0052(5) -0.0016(5) -0.0014(5) C41 0.0278(6) 0.0368(7) 0.0193(5) 0.0024(5) -0.0026(5) 0.0023(6) C42 0.0447(8) 0.0338(7) 0.0258(7) -0.0103(6) 0.0044(6) 0.0060(6) C43 0.0284(7) 0.0577(9) 0.0230(6) -0.0076(6) -0.0018(6) -0.0129(7) _refine_ls_extinction_coef 532.342 _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 O1 . C2 . 1.3429(15) yes O1 . C40 . 1.4827(14) yes C2 . O3 . 1.2094(15) yes C2 . C4 . 1.5239(16) yes C4 . C5 . 1.5559(16) yes C4 . C17 . 1.5537(15) yes C4 . H41 . 0.99 no C5 . C6 . 1.5196(16) yes C5 . C12 . 1.5406(16) yes C5 . H51 . 0.99 no C6 . C7 . 1.3970(17) yes C6 . C11 . 1.3902(18) yes C7 . C8 . 1.3884(18) yes C7 . H71 . 0.97 no C8 . C9 . 1.380(2) yes C8 . H81 . 0.96 no C9 . C10 . 1.383(2) yes C9 . H91 . 0.97 no C10 . C11 . 1.395(2) yes C10 . H101 . 0.98 no C11 . H111 . 0.98 no C12 . C13 . 1.5154(17) yes C12 . H121 . 0.99 no C12 . H122 . 1.00 no C13 . O14 . 1.3425(16) yes C13 . O16 . 1.1980(16) yes O14 . C15 . 1.4517(16) yes C15 . H151 . 0.98 no C15 . H152 . 0.99 no C15 . H153 . 0.99 no C17 . N18 . 1.4777(14) yes C17 . C34 . 1.5293(15) yes C17 . H171 . 1.00 no N18 . C19 . 1.4920(14) yes N18 . C27 . 1.4671(15) yes C19 . C20 . 1.5227(17) yes C19 . C26 . 1.5314(17) yes C19 . H191 . 1.00 no C20 . C21 . 1.3914(18) yes C20 . C25 . 1.3943(18) yes C21 . C22 . 1.3921(19) yes C21 . H211 . 0.98 no C22 . C23 . 1.393(2) yes C22 . H221 . 0.99 no C23 . C24 . 1.382(2) yes C23 . H231 . 0.99 no C24 . C25 . 1.396(2) yes C24 . H241 . 0.97 no C25 . H251 . 0.99 no C26 . H261 . 0.95 no C26 . H262 . 1.01 no C26 . H263 . 1.00 no C27 . C28 . 1.5089(17) yes C27 . H271 . 0.99 no C27 . H272 . 1.02 no C28 . C29 . 1.3926(17) yes C28 . C33 . 1.3917(17) yes C29 . C30 . 1.3933(18) yes C29 . H291 . 1.00 no C30 . C31 . 1.3856(19) yes C30 . H301 . 1.02 no C31 . C32 . 1.390(2) yes C31 . H311 . 0.97 no C32 . C33 . 1.3859(19) yes C32 . H321 . 0.99 no C33 . H331 . 1.00 no C34 . C35 . 1.3937(17) yes C34 . C39 . 1.3984(17) yes C35 . C36 . 1.3921(18) yes C35 . H351 . 0.97 no C36 . C37 . 1.381(2) yes C36 . H361 . 1.01 no C37 . C38 . 1.391(2) yes C37 . H371 . 0.98 no C38 . C39 . 1.3891(18) yes C38 . H381 . 0.99 no C39 . H391 . 0.97 no C40 . C41 . 1.5199(19) yes C40 . C42 . 1.5166(19) yes C40 . C43 . 1.5243(18) yes C41 . H411 . 0.97 no C41 . H412 . 0.99 no C41 . H413 . 1.02 no C42 . H421 . 1.02 no C42 . H422 . 0.97 no C42 . H423 . 1.03 no C43 . H431 . 1.01 no C43 . H432 . 0.99 no C43 . H433 . 0.95 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 . O1 . C40 . 121.78(9) yes O1 . C2 . O3 . 125.25(11) yes O1 . C2 . C4 . 110.44(9) yes O3 . C2 . C4 . 124.29(11) yes C2 . C4 . C5 . 112.27(9) yes C2 . C4 . C17 . 110.72(9) yes C5 . C4 . C17 . 111.51(9) yes C2 . C4 . H41 . 107 no C5 . C4 . H41 . 1069 no C17 . C4 . H41 . 109 no C4 . C5 . C6 . 111.14(9) yes C4 . C5 . C12 . 115.48(9) yes C6 . C5 . C12 . 112.6(1) yes C4 . C5 . H51 . 106 no C6 . C5 . H51 . 107 no C12 . C5 . H51 . 104 no C5 . C6 . C7 . 118.16(11) yes C5 . C6 . C11 . 123.48(11) yes C7 . C6 . C11 . 118.35(11) yes C6 . C7 . C8 . 120.95(12) yes C6 . C7 . H71 . 121 no C8 . C7 . H71 . 118 no C7 . C8 . C9 . 120.13(12) yes C7 . C8 . H81 . 121 no C9 . C8 . H81 . 119 no C8 . C9 . C10 . 119.74(12) yes C8 . C9 . H91 . 121 no C10 . C9 . H91 . 120 no C9 . C10 . C11 . 120.27(13) yes C9 . C10 . H101 . 119 no C11 . C10 . H101 . 120 no C6 . C11 . C10 . 120.56(13) yes C6 . C11 . H111 . 119 no C10 . C11 . H111 . 120 no C5 . C12 . C13 . 109.4(1) yes C5 . C12 . H121 . 113 no C13 . C12 . H121 . 110 no C5 . C12 . H122 . 110 no C13 . C12 . H122 . 106 no H121 . C12 . H122 . 109 no C12 . C13 . O14 . 112.32(11) yes C12 . C13 . O16 . 124.70(12) yes O14 . C13 . O16 . 122.98(12) yes C13 . O14 . C15 . 115.35(11) yes O14 . C15 . H151 . 105 no O14 . C15 . H152 . 108 no H151 . C15 . H152 . 116 no O14 . C15 . H153 . 108 no H151 . C15 . H153 . 112 no H152 . C15 . H153 . 106 no C4 . C17 . N18 . 110.55(9) yes C4 . C17 . C34 . 108.69(9) yes N18 . C17 . C34 . 117.7(1) yes C4 . C17 . H171 . 108 no N18 . C17 . H171 . 105 no C34 . C17 . H171 . 107 no C17 . N18 . C19 . 114.89(9) yes C17 . N18 . C27 . 114.07(9) yes C19 . N18 . C27 . 112.68(9) yes N18 . C19 . C20 . 109.57(9) yes N18 . C19 . C26 . 115.6(1) yes C20 . C19 . C26 . 114.0(1) yes N18 . C19 . H191 . 105 no C20 . C19 . H191 . 106 no C26 . C19 . H191 . 106 no C19 . C20 . C21 . 118.39(11) yes C19 . C20 . C25 . 122.99(11) yes C21 . C20 . C25 . 118.62(12) yes C20 . C21 . C22 . 121.04(12) yes C20 . C21 . H211 . 119 no C22 . C21 . H211 . 119 no C21 . C22 . C23 . 119.83(13) yes C21 . C22 . H221 . 119 no C23 . C22 . H221 . 121 no C22 . C23 . C24 . 119.58(13) yes C22 . C23 . H231 . 121 no C24 . C23 . H231 . 120 no C23 . C24 . C25 . 120.47(12) yes C23 . C24 . H241 . 122 no C25 . C24 . H241 . 117 no C20 . C25 . C24 . 120.44(13) yes C20 . C25 . H251 . 121 no C24 . C25 . H251 . 118 no C19 . C26 . H261 . 110 no C19 . C26 . H262 . 111 no H261 . C26 . H262 . 107 no C19 . C26 . H263 . 110 no H261 . C26 . H263 . 107 no H262 . C26 . H263 . 111 no N18 . C27 . C28 . 113.3(1) yes N18 . C27 . H271 . 108 no C28 . C27 . H271 . 108 no N18 . C27 . H272 . 112 no C28 . C27 . H272 . 109 no H271 . C27 . H272 . 106 no C27 . C28 . C29 . 120.77(11) yes C27 . C28 . C33 . 120.56(11) yes C29 . C28 . C33 . 118.62(11) yes C28 . C29 . C30 . 120.56(12) yes C28 . C29 . H291 . 119 no C30 . C29 . H291 . 121 no C29 . C30 . C31 . 120.21(12) yes C29 . C30 . H301 . 120 no C31 . C30 . H301 . 119 no C30 . C31 . C32 . 119.55(12) yes C30 . C31 . H311 . 122 no C32 . C31 . H311 . 118.76 no C31 . C32 . C33 . 120.08(13) yes C31 . C32 . H321 . 120 no C33 . C32 . H321 . 120 no C28 . C33 . C32 . 120.96(12) yes C28 . C33 . H331 . 118 no C32 . C33 . H331 . 121 no C17 . C34 . C35 . 119.19(11) yes C17 . C34 . C39 . 122.57(11) yes C35 . C34 . C39 . 118.01(11) yes C34 . C35 . C36 . 121.33(12) yes C34 . C35 . H351 . 117 no C36 . C35 . H351 . 122 no C35 . C36 . C37 . 119.85(12) yes C35 . C36 . H361 . 121 no C37 . C36 . H361 . 120 no C36 . C37 . C38 . 119.83(12) yes C36 . C37 . H371 . 120 no C38 . C37 . H371 . 120 no C37 . C38 . C39 . 120.07(13) yes C37 . C38 . H381 . 120 no C39 . C38 . H381 . 120 no C34 . C39 . C38 . 120.88(12) yes C34 . C39 . H391 . 120 no C38 . C39 . H391 . 120 no O1 . C40 . C41 . 111.7(1) yes O1 . C40 . C42 . 101.7(1) yes C41 . C40 . C42 . 110.74(11) yes O1 . C40 . C43 . 109.4(1) yes C41 . C40 . C43 . 111.92(12) yes C42 . C40 . C43 . 110.91(12) yes C40 . C41 . H411 . 108 no C40 . C41 . H412 . 111 no H411 . C41 . H412 . 109 no C40 . C41 . H413 . 110 no H411 . C41 . H413 . 110 no H412 . C41 . H413 . 109 no C40 . C42 . H421 . 108 no C40 . C42 . H422 . 108 no H421 . C42 . H422 . 110 no C40 . C42 . H423 . 109 no H421 . C42 . H423 . 110 no H422 . C42 . H423 . 111 no C40 . C43 . H431 . 109 no C40 . C43 . H432 . 111 no H431 . C43 . H432 . 110 no C40 . C43 . H433 . 109 no H431 . C43 . H433 . 109 no H432 . C43 . H433 . 109 no