# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Eiji Tayama' _publ_contact_author_email TAYAMA@GS.NIIGATA-U.AC.JP _publ_section_title ; New synthetic routes to optically active a-quaternary a-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet-Hauser rearrangements ; loop_ _publ_author_name 'Eiji Tayama' 'Hiroshi Kimura' 'Kiwako Orihara' # Attachment 'C36H51NO4.cif' #------------------------------------------------------------------------------ data_C36H51N1O4 _database_code_depnum_ccdc_archive 'CCDC 693575' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C36 H51 N O4 ' _chemical_formula_moiety 'C36 H51 N O4 ' _chemical_formula_weight 561.80 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _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 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 9.2925(1) _cell_length_b 12.9908(2) _cell_length_c 28.1110(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3393.49(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 183 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25.7 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.140 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.100 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224.00 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Higashi, 1999)' _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 0.992 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_ambient_temperature 296.2 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 22042 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_theta_max 25.68 _diffrn_measured_fraction_theta_max 0.9986 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.9986 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6437 _reflns_number_gt 4910 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1235 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6437 _refine_ls_number_parameters 371 _refine_ls_goodness_of_fit_ref 1.225 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.04800(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.28 _refine_diff_density_min -0.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2792 Friedel Pairs' _refine_ls_abs_structure_Flack 0.07(10) _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.2200(2) 0.8314(1) 0.13420(6) 0.0436(4) Uani 1.00 1 d . . . O(2) O 0.3871(2) 0.7679(2) 0.08489(8) 0.0753(7) Uani 1.00 1 d . . . O(3) O 0.1667(2) 0.3367(1) -0.05872(6) 0.0602(6) Uani 1.00 1 d . . . O(4) O 0.1714(2) 0.3124(1) 0.02052(7) 0.0618(6) Uani 1.00 1 d . . . N(1) N 0.2116(2) 0.5910(1) 0.12728(7) 0.0465(6) Uani 1.00 1 d . . . C(1) C 0.1665(3) 0.6726(1) 0.09368(8) 0.0390(6) Uani 1.00 1 d . . . C(2) C 0.1745(4) 0.6082(2) 0.17721(9) 0.0577(8) Uani 1.00 1 d . . . C(3) C 0.3625(3) 0.5591(2) 0.1237(1) 0.0695(10) Uani 1.00 1 d . . . C(4) C 0.0084(3) 0.7019(2) 0.10270(9) 0.0420(6) Uani 1.00 1 d . . . C(5) C -0.0929(3) 0.6122(2) 0.10278(10) 0.0514(7) Uani 1.00 1 d . . . C(6) C -0.2011(3) 0.5976(2) 0.1318(1) 0.0658(9) Uani 1.00 1 d . . . C(7) C -0.2457(4) 0.6684(3) 0.1700(1) 0.101(1) Uani 1.00 1 d . . . C(8) C 0.2688(3) 0.7630(2) 0.10197(9) 0.0466(7) Uani 1.00 1 d . . . C(9) C 0.1782(3) 0.6323(2) 0.04229(8) 0.0418(6) Uani 1.00 1 d . . . C(10) C 0.1767(3) 0.6966(2) 0.00221(9) 0.0503(7) Uani 1.00 1 d . . . C(11) C 0.1786(3) 0.6520(2) -0.04251(9) 0.0570(8) Uani 1.00 1 d . . . C(12) C 0.1777(3) 0.5471(2) -0.04938(9) 0.0523(8) Uani 1.00 1 d . . . C(13) C 0.1744(3) 0.4824(2) -0.01030(8) 0.0441(6) Uani 1.00 1 d . . . C(14) C 0.1761(3) 0.5257(2) 0.03505(8) 0.0435(6) Uani 1.00 1 d . . . C(15) C 0.1691(4) 0.8127(2) 0.0042(1) 0.078(1) Uani 1.00 1 d . . . C(16) C 0.1706(3) 0.3683(2) -0.01370(9) 0.0480(7) Uani 1.00 1 d . . . C(17) C 0.1668(3) 0.2264(2) -0.07066(10) 0.0595(8) Uani 1.00 1 d . . . C(18) C 0.3014(4) 0.1760(2) -0.0521(1) 0.080(1) Uani 1.00 1 d . . . C(19) C 0.0341(4) 0.1761(3) -0.0515(2) 0.098(1) Uani 1.00 1 d . . . C(20) C 0.1675(5) 0.2285(3) -0.1242(1) 0.094(1) Uani 1.00 1 d . . . C(21) C 0.3236(3) 0.9082(2) 0.15152(10) 0.0530(7) Uani 1.00 1 d . . . C(22) C 0.2442(3) 1.0032(2) 0.17055(9) 0.0497(7) Uani 1.00 1 d . . . C(23) C 0.3626(4) 1.0752(2) 0.1887(1) 0.077(1) Uani 1.00 1 d . . . C(24) C 0.4584(4) 1.0283(3) 0.2263(2) 0.107(1) Uani 1.00 1 d . . . C(25) C 0.5298(4) 0.9273(3) 0.2097(2) 0.102(1) Uani 1.00 1 d . . . C(26) C 0.4134(4) 0.8573(2) 0.1901(1) 0.076(1) Uani 1.00 1 d . . . C(27) C 0.6113(6) 0.8755(4) 0.2502(2) 0.178(2) Uani 1.00 1 d . . . C(28) C 0.1370(3) 1.0576(2) 0.1362(1) 0.0625(9) Uani 1.00 1 d . . . C(29) C 0.2065(6) 1.0742(2) 0.0875(1) 0.109(1) Uani 1.00 1 d . . . C(30) C -0.0011(4) 0.9943(2) 0.1301(2) 0.104(1) Uani 1.00 1 d . . . C(31) C 0.0903(3) 1.1610(2) 0.15868(10) 0.0554(8) Uani 1.00 1 d . . . C(32) C 0.1155(3) 1.2552(2) 0.13726(9) 0.0604(8) Uani 1.00 1 d . . . C(33) C 0.0707(4) 1.3461(2) 0.1576(1) 0.0632(9) Uani 1.00 1 d . . . C(34) C -0.0013(4) 1.3465(2) 0.1995(1) 0.0654(9) Uani 1.00 1 d . . . C(35) C -0.0273(4) 1.2545(2) 0.2221(1) 0.078(1) Uani 1.00 1 d . . . C(36) C 0.0181(4) 1.1628(2) 0.2017(1) 0.075(1) Uani 1.00 1 d . . . H(1) H 0.2354 0.6624 0.1897 0.0734 Uiso 1.00 1 calc . . . H(2) H 0.0778 0.6294 0.1799 0.0734 Uiso 1.00 1 calc . . . H(3) H 0.1907 0.5480 0.1953 0.0734 Uiso 1.00 1 calc . . . H(4) H 0.3777 0.4976 0.1425 0.0852 Uiso 1.00 1 calc . . . H(5) H 0.3884 0.5460 0.0922 0.0852 Uiso 1.00 1 calc . . . H(6) H 0.4235 0.6118 0.1367 0.0852 Uiso 1.00 1 calc . . . H(7) H 0.0019 0.7344 0.1336 0.0509 Uiso 1.00 1 calc . . . H(8) H -0.0220 0.7507 0.0795 0.0509 Uiso 1.00 1 calc . . . H(9) H -0.0769 0.5619 0.0781 0.0652 Uiso 1.00 1 calc . . . H(10) H -0.2558 0.5329 0.1289 0.0826 Uiso 1.00 1 calc . . . H(11) H -0.1880 0.7265 0.1701 0.1281 Uiso 1.00 1 calc . . . H(12) H -0.3453 0.6878 0.1654 0.1281 Uiso 1.00 1 calc . . . H(13) H -0.2405 0.6343 0.2006 0.1281 Uiso 1.00 1 calc . . . H(14) H 0.1781 0.6958 -0.0701 0.0691 Uiso 1.00 1 calc . . . H(15) H 0.1804 0.5183 -0.0813 0.0640 Uiso 1.00 1 calc . . . H(16) H 0.1732 0.4808 0.0626 0.0522 Uiso 1.00 1 calc . . . H(17) H 0.1682 0.8380 0.0361 0.0967 Uiso 1.00 1 calc . . . H(18) H 0.2488 0.8437 -0.0122 0.0967 Uiso 1.00 1 calc . . . H(19) H 0.0821 0.8373 -0.0112 0.0967 Uiso 1.00 1 calc . . . H(20) H 0.3030 0.1042 -0.0585 0.0969 Uiso 1.00 1 calc . . . H(21) H 0.3845 0.2073 -0.0657 0.0969 Uiso 1.00 1 calc . . . H(22) H 0.3085 0.1846 -0.0177 0.0969 Uiso 1.00 1 calc . . . H(23) H 0.0330 0.1837 -0.0171 0.1162 Uiso 1.00 1 calc . . . H(24) H -0.0477 0.2056 -0.0644 0.1162 Uiso 1.00 1 calc . . . H(25) H 0.0375 0.1038 -0.0581 0.1162 Uiso 1.00 1 calc . . . H(26) H 0.2543 0.2656 -0.1357 0.1093 Uiso 1.00 1 calc . . . H(27) H 0.1707 0.1624 -0.1384 0.1093 Uiso 1.00 1 calc . . . H(28) H 0.0874 0.2658 -0.1371 0.1093 Uiso 1.00 1 calc . . . H(29) H 0.3862 0.9299 0.1256 0.0676 Uiso 1.00 1 calc . . . H(30) H 0.1926 0.9806 0.1990 0.0611 Uiso 1.00 1 calc . . . H(31) H 0.4212 1.0921 0.1614 0.0949 Uiso 1.00 1 calc . . . H(32) H 0.3181 1.1370 0.1995 0.0949 Uiso 1.00 1 calc . . . H(33) H 0.5271 1.0759 0.2372 0.1240 Uiso 1.00 1 calc . . . H(34) H 0.3966 1.0112 0.2542 0.1240 Uiso 1.00 1 calc . . . H(35) H 0.5949 0.9431 0.1833 0.1347 Uiso 1.00 1 calc . . . H(36) H 0.3504 0.8408 0.2175 0.1007 Uiso 1.00 1 calc . . . H(37) H 0.4545 0.7944 0.1800 0.1007 Uiso 1.00 1 calc . . . H(38) H 0.5429 0.8556 0.2753 0.1968 Uiso 1.00 1 calc . . . H(39) H 0.6505 0.8079 0.2394 0.1968 Uiso 1.00 1 calc . . . H(40) H 0.6840 0.9133 0.2628 0.1968 Uiso 1.00 1 calc . . . H(41) H 0.2351 1.0137 0.0723 0.1232 Uiso 1.00 1 calc . . . H(42) H 0.1457 1.1138 0.0664 0.1232 Uiso 1.00 1 calc . . . H(43) H 0.2949 1.1175 0.0911 0.1232 Uiso 1.00 1 calc . . . H(44) H -0.0432 0.9835 0.1596 0.1351 Uiso 1.00 1 calc . . . H(45) H -0.0638 1.0296 0.1091 0.1351 Uiso 1.00 1 calc . . . H(46) H 0.0247 0.9294 0.1158 0.1351 Uiso 1.00 1 calc . . . H(47) H 0.1670 1.2560 0.1079 0.0693 Uiso 1.00 1 calc . . . H(48) H 0.0873 1.4097 0.1418 0.0726 Uiso 1.00 1 calc . . . H(49) H -0.0345 1.4101 0.2133 0.0833 Uiso 1.00 1 calc . . . H(50) H -0.0774 1.2503 0.2517 0.0928 Uiso 1.00 1 calc . . . H(51) H 0.0024 1.0997 0.2183 0.0840 Uiso 1.00 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0425(9) 0.0338(7) 0.0546(10) -0.0037(7) -0.0007(8) -0.0117(7) O(2) 0.050(1) 0.077(1) 0.099(2) -0.019(1) 0.023(1) -0.040(1) O(3) 0.081(1) 0.0500(9) 0.049(1) 0.0102(10) -0.0047(10) -0.0206(8) O(4) 0.085(1) 0.0454(9) 0.055(1) 0.0008(9) 0.004(1) -0.0118(9) N(1) 0.056(1) 0.0405(9) 0.042(1) 0.0122(9) -0.0059(10) -0.0056(9) C(1) 0.044(1) 0.0322(10) 0.041(1) 0.001(1) 0.002(1) -0.0060(10) C(2) 0.086(2) 0.046(1) 0.041(1) 0.009(1) -0.004(1) -0.007(1) C(3) 0.073(2) 0.070(2) 0.065(2) 0.025(2) -0.019(2) -0.015(1) C(4) 0.043(1) 0.0330(10) 0.050(1) 0.0014(10) 0.001(1) -0.0079(10) C(5) 0.050(2) 0.042(1) 0.063(2) -0.004(1) 0.009(1) -0.016(1) C(6) 0.060(2) 0.052(1) 0.085(2) -0.014(1) 0.011(2) -0.013(1) C(7) 0.077(3) 0.122(3) 0.103(3) -0.023(2) 0.041(2) -0.034(2) C(8) 0.044(2) 0.045(1) 0.051(1) -0.002(1) 0.004(1) -0.013(1) C(9) 0.044(1) 0.039(1) 0.042(1) 0.002(1) 0.001(1) -0.0067(10) C(10) 0.060(2) 0.044(1) 0.047(2) -0.001(1) 0.006(1) -0.001(1) C(11) 0.070(2) 0.059(1) 0.042(1) 0.004(1) 0.007(1) 0.003(1) C(12) 0.056(2) 0.061(1) 0.040(1) 0.007(1) -0.001(1) -0.010(1) C(13) 0.045(1) 0.049(1) 0.039(1) 0.006(1) -0.001(1) -0.007(1) C(14) 0.049(2) 0.039(1) 0.043(1) 0.006(1) 0.002(1) -0.0072(10) C(15) 0.125(3) 0.046(1) 0.064(2) -0.002(2) 0.009(2) 0.005(1) C(16) 0.048(2) 0.050(1) 0.046(1) 0.004(1) 0.000(1) -0.014(1) C(17) 0.066(2) 0.052(1) 0.060(2) 0.007(1) -0.004(2) -0.027(1) C(18) 0.075(2) 0.076(2) 0.088(2) 0.023(2) -0.010(2) -0.030(2) C(19) 0.079(3) 0.097(2) 0.119(3) -0.016(2) -0.006(2) -0.047(2) C(20) 0.133(3) 0.078(2) 0.070(2) 0.025(2) -0.023(2) -0.040(2) C(21) 0.047(2) 0.046(1) 0.065(2) -0.009(1) 0.001(1) -0.018(1) C(22) 0.058(2) 0.034(1) 0.057(2) -0.006(1) -0.005(1) -0.007(1) C(23) 0.074(2) 0.052(1) 0.105(3) -0.010(1) -0.015(2) -0.026(2) C(24) 0.084(3) 0.089(2) 0.148(4) 0.022(2) -0.059(3) -0.068(2) C(25) 0.076(3) 0.093(2) 0.137(3) 0.025(2) -0.043(2) -0.068(2) C(26) 0.068(2) 0.062(2) 0.099(2) 0.023(1) -0.031(2) -0.034(2) C(27) 0.155(5) 0.154(4) 0.224(6) 0.087(4) -0.133(5) -0.118(4) C(28) 0.089(2) 0.032(1) 0.067(2) -0.002(1) -0.019(2) -0.001(1) C(29) 0.209(5) 0.058(2) 0.058(2) 0.027(2) -0.001(3) -0.004(1) C(30) 0.091(3) 0.048(1) 0.173(4) 0.010(2) -0.070(3) -0.023(2) C(31) 0.076(2) 0.035(1) 0.056(2) -0.001(1) -0.011(1) 0.002(1) C(32) 0.089(2) 0.039(1) 0.053(2) -0.004(1) -0.003(1) 0.002(1) C(33) 0.095(2) 0.031(1) 0.064(2) -0.003(1) -0.011(2) 0.004(1) C(34) 0.090(2) 0.043(1) 0.063(2) 0.007(1) 0.000(2) -0.001(1) C(35) 0.099(3) 0.064(2) 0.070(2) 0.017(2) 0.019(2) 0.009(2) C(36) 0.101(3) 0.043(1) 0.079(2) -0.003(2) 0.002(2) 0.021(2) #------------------------------------------------------------------------------ _computing_data_collection 'Rapid Auto Ver.1.06' _computing_cell_refinement 'Rapid Auto Ver.1.06' _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 2.0' _computing_publication_material 'teXsan Ver. 2.0' _computing_molecular_graphics ? #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(8) 1.348(3) . . yes O(1) C(21) 1.469(3) . . yes O(2) C(8) 1.201(3) . . yes O(3) C(16) 1.331(3) . . yes O(3) C(17) 1.472(3) . . yes O(4) C(16) 1.205(3) . . yes N(1) C(1) 1.481(3) . . yes N(1) C(2) 1.462(3) . . yes N(1) C(3) 1.466(4) . . yes C(1) C(4) 1.538(3) . . yes C(1) C(8) 1.528(3) . . yes C(1) C(9) 1.541(3) . . yes C(2) H(1) 0.970 . . no C(2) H(2) 0.943 . . no C(2) H(3) 0.945 . . no C(3) H(4) 0.968 . . no C(3) H(5) 0.934 . . no C(3) H(6) 0.962 . . no C(4) C(5) 1.498(3) . . yes C(4) H(7) 0.968 . . no C(4) H(8) 0.953 . . no C(5) C(6) 1.308(4) . . yes C(5) H(9) 0.965 . . no C(6) C(7) 1.474(4) . . yes C(6) H(10) 0.986 . . no C(7) H(11) 0.926 . . no C(7) H(12) 0.968 . . no C(7) H(13) 0.967 . . no C(9) C(10) 1.403(3) . . yes C(9) C(14) 1.399(3) . . yes C(10) C(11) 1.385(4) . . yes C(10) C(15) 1.511(3) . . yes C(11) C(12) 1.376(4) . . yes C(11) H(14) 0.963 . . no C(12) C(13) 1.384(3) . . yes C(12) H(15) 0.971 . . no C(13) C(14) 1.394(3) . . yes C(13) C(16) 1.485(3) . . yes C(14) H(16) 0.970 . . no C(15) H(17) 0.953 . . no C(15) H(18) 0.961 . . no C(15) H(19) 0.972 . . no C(17) C(18) 1.505(4) . . yes C(17) C(19) 1.495(5) . . yes C(17) C(20) 1.505(4) . . yes C(18) H(20) 0.950 . . no C(18) H(21) 0.952 . . no C(18) H(22) 0.976 . . no C(19) H(23) 0.970 . . no C(19) H(24) 0.926 . . no C(19) H(25) 0.958 . . no C(20) H(26) 0.993 . . no C(20) H(27) 0.948 . . no C(20) H(28) 0.960 . . no C(21) C(22) 1.535(3) . . yes C(21) C(26) 1.519(4) . . yes C(21) H(29) 0.975 . . no C(22) C(23) 1.531(4) . . yes C(22) C(28) 1.557(4) . . yes C(22) H(30) 0.977 . . no C(23) C(24) 1.510(5) . . yes C(23) H(31) 0.965 . . no C(23) H(32) 0.952 . . no C(24) C(25) 1.542(5) . . yes C(24) H(33) 0.942 . . no C(24) H(34) 0.999 . . no C(25) C(26) 1.518(4) . . yes C(25) C(27) 1.524(7) . . yes C(25) H(35) 0.978 . . no C(26) H(36) 0.991 . . no C(26) H(37) 0.945 . . no C(27) H(38) 0.985 . . no C(27) H(39) 0.999 . . no C(27) H(40) 0.908 . . no C(28) C(29) 1.529(5) . . yes C(28) C(30) 1.533(5) . . yes C(28) C(31) 1.547(4) . . yes C(29) H(41) 0.934 . . no C(29) H(42) 0.967 . . no C(29) H(43) 1.000 . . no C(30) H(44) 0.927 . . no C(30) H(45) 0.948 . . no C(30) H(46) 0.964 . . no C(31) C(32) 1.383(3) . . yes C(31) C(36) 1.382(4) . . yes C(32) C(33) 1.376(4) . . yes C(32) H(47) 0.954 . . no C(33) C(34) 1.355(4) . . yes C(33) H(48) 0.951 . . no C(34) C(35) 1.374(4) . . yes C(34) H(49) 0.965 . . no C(35) C(36) 1.388(4) . . yes C(35) H(50) 0.956 . . no C(36) H(51) 0.956 . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(8) O(1) C(21) 116.7(2) . . . yes C(16) O(3) C(17) 121.1(2) . . . yes C(1) N(1) C(2) 115.9(2) . . . yes C(1) N(1) C(3) 115.4(2) . . . yes C(2) N(1) C(3) 109.5(2) . . . yes N(1) C(1) C(4) 110.0(2) . . . yes N(1) C(1) C(8) 106.1(2) . . . yes N(1) C(1) C(9) 109.5(2) . . . yes C(4) C(1) C(8) 112.3(2) . . . yes C(4) C(1) C(9) 107.8(2) . . . yes C(8) C(1) C(9) 111.1(2) . . . yes N(1) C(2) H(1) 108.8 . . . no N(1) C(2) H(2) 110.2 . . . no N(1) C(2) H(3) 110.7 . . . no H(1) C(2) H(2) 108.3 . . . no H(1) C(2) H(3) 108.2 . . . no H(2) C(2) H(3) 110.5 . . . no N(1) C(3) H(4) 109.6 . . . no N(1) C(3) H(5) 111.3 . . . no N(1) C(3) H(6) 109.6 . . . no H(4) C(3) H(5) 109.3 . . . no H(4) C(3) H(6) 107.0 . . . no H(5) C(3) H(6) 109.8 . . . no C(1) C(4) C(5) 114.1(2) . . . yes C(1) C(4) H(7) 108.4 . . . no C(1) C(4) H(8) 109.6 . . . no C(5) C(4) H(7) 107.4 . . . no C(5) C(4) H(8) 109.4 . . . no H(7) C(4) H(8) 107.7 . . . no C(4) C(5) C(6) 126.6(2) . . . yes C(4) C(5) H(9) 115.4 . . . no C(6) C(5) H(9) 117.9 . . . no C(5) C(6) C(7) 125.5(3) . . . yes C(5) C(6) H(10) 118.0 . . . no C(7) C(6) H(10) 116.5 . . . no C(6) C(7) H(11) 110.3 . . . no C(6) C(7) H(12) 109.5 . . . no C(6) C(7) H(13) 110.4 . . . no H(11) C(7) H(12) 110.0 . . . no H(11) C(7) H(13) 110.1 . . . no H(12) C(7) H(13) 106.6 . . . no O(1) C(8) O(2) 122.8(2) . . . yes O(1) C(8) C(1) 113.6(2) . . . yes O(2) C(8) C(1) 123.3(2) . . . yes C(1) C(9) C(10) 123.3(2) . . . yes C(1) C(9) C(14) 118.2(2) . . . yes C(10) C(9) C(14) 118.2(2) . . . yes C(9) C(10) C(11) 118.7(2) . . . yes C(9) C(10) C(15) 124.4(2) . . . yes C(11) C(10) C(15) 116.9(2) . . . yes C(10) C(11) C(12) 122.8(2) . . . yes C(10) C(11) H(14) 119.0 . . . no C(12) C(11) H(14) 118.1 . . . no C(11) C(12) C(13) 119.4(2) . . . yes C(11) C(12) H(15) 120.7 . . . no C(13) C(12) H(15) 119.9 . . . no C(12) C(13) C(14) 118.7(2) . . . yes C(12) C(13) C(16) 123.8(2) . . . yes C(14) C(13) C(16) 117.5(2) . . . yes C(9) C(14) C(13) 122.2(2) . . . yes C(9) C(14) H(16) 118.7 . . . no C(13) C(14) H(16) 119.1 . . . no C(10) C(15) H(17) 112.3 . . . no C(10) C(15) H(18) 111.4 . . . no C(10) C(15) H(19) 110.5 . . . no H(17) C(15) H(18) 108.3 . . . no H(17) C(15) H(19) 107.4 . . . no H(18) C(15) H(19) 106.8 . . . no O(3) C(16) O(4) 125.0(2) . . . yes O(3) C(16) C(13) 111.7(2) . . . yes O(4) C(16) C(13) 123.3(2) . . . yes O(3) C(17) C(18) 110.1(2) . . . yes O(3) C(17) C(19) 110.0(2) . . . yes O(3) C(17) C(20) 102.1(2) . . . yes C(18) C(17) C(19) 111.8(3) . . . yes C(18) C(17) C(20) 110.6(3) . . . yes C(19) C(17) C(20) 111.9(3) . . . yes C(17) C(18) H(20) 112.0 . . . no C(17) C(18) H(21) 110.4 . . . no C(17) C(18) H(22) 110.5 . . . no H(20) C(18) H(21) 109.3 . . . no H(20) C(18) H(22) 107.3 . . . no H(21) C(18) H(22) 107.1 . . . no C(17) C(19) H(23) 108.9 . . . no C(17) C(19) H(24) 110.8 . . . no C(17) C(19) H(25) 109.3 . . . no H(23) C(19) H(24) 109.8 . . . no H(23) C(19) H(25) 107.1 . . . no H(24) C(19) H(25) 110.9 . . . no C(17) C(20) H(26) 109.8 . . . no C(17) C(20) H(27) 113.8 . . . no C(17) C(20) H(28) 112.6 . . . no H(26) C(20) H(27) 106.1 . . . no H(26) C(20) H(28) 105.2 . . . no H(27) C(20) H(28) 108.8 . . . no O(1) C(21) C(22) 110.3(2) . . . yes O(1) C(21) C(26) 107.5(2) . . . yes O(1) C(21) H(29) 109.9 . . . no C(22) C(21) C(26) 111.4(2) . . . yes C(22) C(21) H(29) 108.4 . . . no C(26) C(21) H(29) 109.4 . . . no C(21) C(22) C(23) 105.2(2) . . . yes C(21) C(22) C(28) 117.2(2) . . . yes C(21) C(22) H(30) 106.2 . . . no C(23) C(22) C(28) 112.9(2) . . . yes C(23) C(22) H(30) 105.2 . . . no C(28) C(22) H(30) 109.3 . . . no C(22) C(23) C(24) 114.2(3) . . . yes C(22) C(23) H(31) 106.2 . . . no C(22) C(23) H(32) 108.0 . . . no C(24) C(23) H(31) 108.3 . . . no C(24) C(23) H(32) 111.9 . . . no H(31) C(23) H(32) 108.0 . . . no C(23) C(24) C(25) 112.8(3) . . . yes C(23) C(24) H(33) 111.3 . . . no C(23) C(24) H(34) 107.6 . . . no C(25) C(24) H(33) 111.5 . . . no C(25) C(24) H(34) 107.2 . . . no H(33) C(24) H(34) 106.1 . . . no C(24) C(25) C(26) 108.2(3) . . . yes C(24) C(25) C(27) 111.3(3) . . . yes C(24) C(25) H(35) 108.5 . . . no C(26) C(25) C(27) 111.2(4) . . . yes C(26) C(25) H(35) 106.9 . . . no C(27) C(25) H(35) 110.6 . . . no C(21) C(26) C(25) 113.0(3) . . . yes C(21) C(26) H(36) 108.9 . . . no C(21) C(26) H(37) 112.7 . . . no C(25) C(26) H(36) 105.6 . . . no C(25) C(26) H(37) 109.8 . . . no H(36) C(26) H(37) 106.5 . . . no C(25) C(27) H(38) 109.3 . . . no C(25) C(27) H(39) 110.0 . . . no C(25) C(27) H(40) 115.1 . . . no H(38) C(27) H(39) 102.9 . . . no H(38) C(27) H(40) 110.0 . . . no H(39) C(27) H(40) 108.9 . . . no C(22) C(28) C(29) 110.4(3) . . . yes C(22) C(28) C(30) 111.2(2) . . . yes C(22) C(28) C(31) 108.7(2) . . . yes C(29) C(28) C(30) 109.2(3) . . . yes C(29) C(28) C(31) 111.2(2) . . . yes C(30) C(28) C(31) 106.1(3) . . . yes C(28) C(29) H(41) 114.4 . . . no C(28) C(29) H(42) 112.1 . . . no C(28) C(29) H(43) 109.6 . . . no H(41) C(29) H(42) 109.4 . . . no H(41) C(29) H(43) 106.6 . . . no H(42) C(29) H(43) 104.1 . . . no C(28) C(30) H(44) 109.5 . . . no C(28) C(30) H(45) 108.9 . . . no C(28) C(30) H(46) 108.0 . . . no H(44) C(30) H(45) 111.7 . . . no H(44) C(30) H(46) 110.3 . . . no H(45) C(30) H(46) 108.5 . . . no C(28) C(31) C(32) 122.9(3) . . . yes C(28) C(31) C(36) 120.5(2) . . . yes C(32) C(31) C(36) 116.6(2) . . . yes C(31) C(32) C(33) 121.8(3) . . . yes C(31) C(32) H(47) 118.1 . . . no C(33) C(32) H(47) 120.1 . . . no C(32) C(33) C(34) 120.9(2) . . . yes C(32) C(33) H(48) 120.2 . . . no C(34) C(33) H(48) 118.9 . . . no C(33) C(34) C(35) 119.0(3) . . . yes C(33) C(34) H(49) 120.8 . . . no C(35) C(34) H(49) 120.2 . . . no C(34) C(35) C(36) 120.1(3) . . . yes C(34) C(35) H(50) 122.6 . . . no C(36) C(35) H(50) 117.4 . . . no C(31) C(36) C(35) 121.6(3) . . . yes C(31) C(36) H(51) 119.2 . . . no C(35) C(36) H(51) 119.2 . . . no #------------------------------------------------------------------------------ # END of CIF #------------------------------------------------------------------------------