Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'P. Bailey' _publ_contact_author_address ; School of Chemistry University of Manchester Faraday Building Sackville Street Manchester M60 1QD UNITED KINGDOM ; _publ_contact_author_email R.Pettecrew@postgrad.manchester.ac.uk _publ_section_title ; Conformational and spacial preferences for substrates of PepT1 ; _publ_requested_category FO loop_ _publ_author_name P.Bailey B.C.A.Richard 'Ian D.Collier' 'George L.Kellett' ; D.Meredith ; 'Keith M.Morgan' 'Rachel Pettecrew' 'Richard A.Price' 'Robin G.Pritcharda' data_r _database_code_depnum_ccdc_archive 'CCDC 278679' _audit_creation_date 2004-05-27T15:49:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H28 N2 O5' _chemical_formula_sum 'C16 H28 N2 O5' _chemical_formula_weight 328.4 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.90450(10) _cell_length_b 16.7946(4) _cell_length_c 18.1015(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1795.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7375 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.373 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.9779 _exptl_absorpt_correction_T_max 0.9964 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.123878 _diffrn_orient_matrix_ub_12 0.17182E-2 _diffrn_orient_matrix_ub_13 0.376376E-1 _diffrn_orient_matrix_ub_21 -0.105473 _diffrn_orient_matrix_ub_22 -0.259167E-1 _diffrn_orient_matrix_ub_23 -0.359176E-1 _diffrn_orient_matrix_ub_31 0.470454E-1 _diffrn_orient_matrix_ub_32 -0.535793E-1 _diffrn_orient_matrix_ub_33 0.185806E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0421 _diffrn_reflns_number 9889 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 26.31 _diffrn_reflns_theta_full 26.31 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 3566 _reflns_number_gt 3216 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.0927P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3566 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0712 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(7) _refine_diff_density_max 0.139 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.6700(2) 0.79771(8) 0.56168(7) 0.0174(3) Uani 1 1 d . . . C3 C 0.6527(2) 0.88067(8) 0.52831(8) 0.0208(3) Uani 1 1 d . . . C4 C 0.7056(3) 0.93468(9) 0.59374(9) 0.0298(4) Uani 1 1 d . . . C5 C 0.8755(3) 0.88498(8) 0.63720(9) 0.0267(3) Uani 1 1 d . . . C6 C 0.8627(2) 0.73559(8) 0.66736(7) 0.0215(3) Uani 1 1 d . . . C7 C 1.1199(3) 0.72678(10) 0.67162(9) 0.0301(3) Uani 1 1 d . . . C8 C 0.7566(2) 0.74157(8) 0.74423(8) 0.0224(3) Uani 1 1 d . . . C9 C 0.7375(2) 0.66648(9) 0.86142(8) 0.0254(3) Uani 1 1 d . . . C10 C 0.4810(3) 0.66882(12) 0.86763(10) 0.0353(4) Uani 1 1 d . . . C11 C 0.8528(3) 0.72939(10) 0.90827(9) 0.0317(4) Uani 1 1 d . . . C12 C 0.8261(3) 0.58394(10) 0.87885(10) 0.0356(4) Uani 1 1 d . . . C13 C 0.4001(2) 0.96000(8) 0.45372(7) 0.0193(3) Uani 1 1 d . . . C14 C 0.1409(2) 1.01843(8) 0.36258(7) 0.0220(3) Uani 1 1 d . . . C15 C -0.0571(3) 0.98152(10) 0.32161(9) 0.0299(3) Uani 1 1 d . . . C16 C 0.0657(3) 1.08811(10) 0.40946(9) 0.0304(4) Uani 1 1 d . . . C17 C 0.3273(3) 1.04101(11) 0.30885(9) 0.0311(4) Uani 1 1 d . . . N1 N 0.79444(19) 0.80363(6) 0.62366(6) 0.0195(2) Uani 1 1 d . . . N2 N 0.43501(19) 0.89231(7) 0.49300(6) 0.0212(3) Uani 1 1 d . . . O2 O 0.58714(15) 0.73666(5) 0.53574(5) 0.0215(2) Uani 1 1 d . . . O8 O 0.64332(19) 0.79655(6) 0.76578(6) 0.0329(3) Uani 1 1 d . . . O9 O 0.80809(16) 0.67615(6) 0.78305(5) 0.0243(2) Uani 1 1 d . . . O13 O 0.52038(15) 1.01841(5) 0.45739(6) 0.0255(2) Uani 1 1 d . . . O14 O 0.21413(16) 0.95206(5) 0.41089(5) 0.0233(2) Uani 1 1 d . . . H2 H 0.343(3) 0.8513(9) 0.4862(8) 0.022(4) Uiso 1 1 d . . . H3 H 0.773(3) 0.8860(8) 0.4910(8) 0.019(4) Uiso 1 1 d . . . H4A H 0.564(3) 0.9400(9) 0.6242(9) 0.033(4) Uiso 1 1 d . . . H4B H 0.763(3) 0.9879(12) 0.5791(10) 0.048(5) Uiso 1 1 d . . . H5A H 0.871(3) 0.8975(9) 0.6917(10) 0.030(4) Uiso 1 1 d . . . H5B H 1.034(3) 0.8921(9) 0.6175(9) 0.034(4) Uiso 1 1 d . . . H6 H 0.791(2) 0.6858(9) 0.6431(8) 0.022(4) Uiso 1 1 d . . . H7A H 1.194(3) 0.7714(11) 0.6997(10) 0.039(5) Uiso 1 1 d . . . H7B H 1.161(3) 0.6756(11) 0.6975(10) 0.046(5) Uiso 1 1 d . . . H7C H 1.186(3) 0.7227(11) 0.6221(12) 0.049(5) Uiso 1 1 d . . . H10A H 0.411(4) 0.6275(12) 0.8333(11) 0.055(6) Uiso 1 1 d . . . H10B H 0.421(3) 0.7214(12) 0.8588(11) 0.051(5) Uiso 1 1 d . . . H10C H 0.452(4) 0.6531(12) 0.9179(12) 0.058(6) Uiso 1 1 d . . . H11A H 0.799(3) 0.7841(11) 0.8959(10) 0.038(5) Uiso 1 1 d . . . H11B H 1.028(3) 0.7270(10) 0.9026(10) 0.045(5) Uiso 1 1 d . . . H11C H 0.815(3) 0.7214(9) 0.9597(11) 0.038(4) Uiso 1 1 d . . . H12A H 0.751(3) 0.5433(10) 0.8435(11) 0.044(5) Uiso 1 1 d . . . H12B H 0.992(3) 0.5829(10) 0.8715(10) 0.043(5) Uiso 1 1 d . . . H12C H 0.791(3) 0.5722(10) 0.9316(10) 0.039(5) Uiso 1 1 d . . . H15A H -0.176(3) 0.9672(10) 0.3555(10) 0.039(5) Uiso 1 1 d . . . H15B H -0.006(3) 0.9338(11) 0.2911(10) 0.040(5) Uiso 1 1 d . . . H15C H -0.120(3) 1.0208(10) 0.2861(9) 0.034(4) Uiso 1 1 d . . . H16A H -0.052(4) 1.0705(11) 0.4452(11) 0.055(6) Uiso 1 1 d . . . H16B H 0.196(3) 1.1113(9) 0.4380(9) 0.033(4) Uiso 1 1 d . . . H16C H -0.008(3) 1.1265(12) 0.3763(11) 0.054(5) Uiso 1 1 d . . . H17A H 0.384(3) 0.9934(11) 0.2823(10) 0.047(5) Uiso 1 1 d . . . H17B H 0.266(3) 1.0769(10) 0.2699(11) 0.043(5) Uiso 1 1 d . . . H17C H 0.454(3) 1.0690(9) 0.3318(9) 0.031(4) Uiso 1 1 d . . . 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 C2 0.0156(6) 0.0191(7) 0.0173(7) 0.0016(5) 0.0020(5) 0.0014(5) C3 0.0205(7) 0.0190(7) 0.0230(7) 0.0022(6) -0.0047(5) -0.0005(5) C4 0.0389(9) 0.0173(8) 0.0331(9) -0.0007(6) -0.0147(7) -0.0008(6) C5 0.0319(8) 0.0195(7) 0.0287(8) -0.0013(6) -0.0114(6) -0.0022(6) C6 0.0249(7) 0.0209(7) 0.0187(7) 0.0019(6) -0.0024(5) 0.0053(5) C7 0.0265(8) 0.0376(10) 0.0262(8) 0.0070(7) 0.0023(6) 0.0102(6) C8 0.0213(7) 0.0237(7) 0.0224(7) 0.0009(6) -0.0026(5) 0.0029(6) C9 0.0282(7) 0.0306(8) 0.0174(7) 0.0043(6) 0.0031(6) 0.0039(6) C10 0.0291(8) 0.0441(10) 0.0327(10) 0.0030(9) 0.0070(7) -0.0007(7) C11 0.0351(9) 0.0355(9) 0.0244(8) 0.0008(7) -0.0024(7) 0.0023(7) C12 0.0481(11) 0.0337(9) 0.0251(9) 0.0096(7) 0.0053(7) 0.0080(7) C13 0.0183(6) 0.0209(7) 0.0188(6) 0.0002(6) -0.0010(5) 0.0026(5) C14 0.0230(7) 0.0221(7) 0.0208(7) 0.0059(6) -0.0034(5) 0.0056(5) C15 0.0264(8) 0.0365(8) 0.0268(8) 0.0030(8) -0.0066(6) 0.0039(7) C16 0.0346(9) 0.0272(8) 0.0293(8) 0.0023(7) -0.0034(7) 0.0107(7) C17 0.0295(8) 0.0392(9) 0.0246(8) 0.0069(8) 0.0007(6) 0.0004(7) N1 0.0242(6) 0.0162(5) 0.0179(6) 0.0004(5) -0.0040(4) 0.0005(4) N2 0.0205(6) 0.0163(6) 0.0268(6) 0.0027(5) -0.0065(5) -0.0016(5) O2 0.0227(5) 0.0171(5) 0.0246(5) -0.0013(4) -0.0040(4) 0.0000(4) O8 0.0410(6) 0.0313(6) 0.0262(6) 0.0026(5) 0.0047(5) 0.0169(5) O9 0.0299(5) 0.0244(5) 0.0188(5) 0.0042(4) 0.0032(4) 0.0075(4) O13 0.0255(5) 0.0208(5) 0.0304(6) 0.0048(4) -0.0054(4) -0.0042(4) O14 0.0229(5) 0.0201(5) 0.0269(5) 0.0051(4) -0.0087(4) 0.0007(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O2 1.2291(15) . ? C2 N1 1.3450(17) . ? C2 C3 1.5221(19) . ? C3 N2 1.4488(17) . ? C3 C4 1.524(2) . ? C3 H3 0.985(15) . ? C4 C5 1.524(2) . ? C4 H4A 1.008(18) . ? C4 H4B 0.99(2) . ? C5 N1 1.4683(18) . ? C5 H5A 1.009(17) . ? C5 H5B 1.008(18) . ? C6 N1 1.4472(17) . ? C6 C7 1.527(2) . ? C6 C8 1.5294(19) . ? C6 H6 1.035(15) . ? C7 H7A 1.007(18) . ? C7 H7B 1.01(2) . ? C7 H7C 0.98(2) . ? C8 O8 1.2050(16) . ? C8 O9 1.3392(16) . ? C9 O9 1.4873(17) . ? C9 C12 1.515(2) . ? C9 C11 1.516(2) . ? C9 C10 1.519(2) . ? C10 H10A 1.02(2) . ? C10 H10B 0.96(2) . ? C10 H10C 0.96(2) . ? C11 H11A 0.997(18) . ? C11 H11B 1.04(2) . ? C11 H11C 0.967(19) . ? C12 H12A 1.037(19) . ? C12 H12B 0.99(2) . ? C12 H12C 0.996(19) . ? C13 O13 1.2129(15) . ? C13 O14 1.3507(16) . ? C13 N2 1.3565(17) . ? C14 O14 1.4812(16) . ? C14 C16 1.512(2) . ? C14 C17 1.517(2) . ? C14 C15 1.517(2) . ? C15 H15A 0.963(19) . ? C15 H15B 1.020(18) . ? C15 H15C 0.993(18) . ? C16 H16A 1.00(2) . ? C16 H16B 1.003(18) . ? C16 H16C 0.98(2) . ? C17 H17A 0.992(19) . ? C17 H17B 0.996(19) . ? C17 H17C 0.978(18) . ? N2 H2 0.884(16) . ? 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_3 _geom_angle_publ_flag O2 C2 N1 126.71(11) . . ? O2 C2 C3 125.83(11) . . ? N1 C2 C3 107.46(10) . . ? N2 C3 C2 110.98(10) . . ? N2 C3 C4 116.38(12) . . ? C2 C3 C4 102.87(11) . . ? N2 C3 H3 109.0(8) . . ? C2 C3 H3 107.8(8) . . ? C4 C3 H3 109.4(9) . . ? C5 C4 C3 102.13(12) . . ? C5 C4 H4A 108.2(9) . . ? C3 C4 H4A 107.9(9) . . ? C5 C4 H4B 114.0(11) . . ? C3 C4 H4B 113.5(11) . . ? H4A C4 H4B 110.6(14) . . ? N1 C5 C4 102.05(11) . . ? N1 C5 H5A 110.4(9) . . ? C4 C5 H5A 111.9(9) . . ? N1 C5 H5B 110.7(9) . . ? C4 C5 H5B 111.3(9) . . ? H5A C5 H5B 110.2(13) . . ? N1 C6 C7 112.40(12) . . ? N1 C6 C8 109.34(11) . . ? C7 C6 C8 111.58(12) . . ? N1 C6 H6 107.0(8) . . ? C7 C6 H6 110.4(8) . . ? C8 C6 H6 105.8(8) . . ? C6 C7 H7A 112.8(10) . . ? C6 C7 H7B 110.2(11) . . ? H7A C7 H7B 107.1(14) . . ? C6 C7 H7C 111.0(11) . . ? H7A C7 H7C 109.9(15) . . ? H7B C7 H7C 105.6(16) . . ? O8 C8 O9 125.79(13) . . ? O8 C8 C6 124.92(12) . . ? O9 C8 C6 109.29(11) . . ? O9 C9 C12 101.65(11) . . ? O9 C9 C11 109.36(12) . . ? C12 C9 C11 111.48(13) . . ? O9 C9 C10 110.31(13) . . ? C12 C9 C10 110.63(14) . . ? C11 C9 C10 112.83(14) . . ? C9 C10 H10A 109.9(13) . . ? C9 C10 H10B 112.3(12) . . ? H10A C10 H10B 111.9(17) . . ? C9 C10 H10C 104.1(13) . . ? H10A C10 H10C 108.4(17) . . ? H10B C10 H10C 110.0(17) . . ? C9 C11 H11A 112.0(10) . . ? C9 C11 H11B 111.3(10) . . ? H11A C11 H11B 109.2(15) . . ? C9 C11 H11C 109.8(10) . . ? H11A C11 H11C 105.7(15) . . ? H11B C11 H11C 108.6(15) . . ? C9 C12 H12A 109.0(10) . . ? C9 C12 H12B 109.3(11) . . ? H12A C12 H12B 109.4(15) . . ? C9 C12 H12C 107.9(10) . . ? H12A C12 H12C 111.8(15) . . ? H12B C12 H12C 109.4(15) . . ? O13 C13 O14 125.96(12) . . ? O13 C13 N2 124.06(12) . . ? O14 C13 N2 109.98(11) . . ? O14 C14 C16 109.67(11) . . ? O14 C14 C17 110.80(11) . . ? C16 C14 C17 112.30(13) . . ? O14 C14 C15 101.89(11) . . ? C16 C14 C15 111.36(12) . . ? C17 C14 C15 110.36(12) . . ? C14 C15 H15A 110.7(10) . . ? C14 C15 H15B 110.9(10) . . ? H15A C15 H15B 111.5(14) . . ? C14 C15 H15C 109.6(10) . . ? H15A C15 H15C 107.7(14) . . ? H15B C15 H15C 106.4(13) . . ? C14 C16 H16A 109.9(11) . . ? C14 C16 H16B 111.4(10) . . ? H16A C16 H16B 108.3(15) . . ? C14 C16 H16C 107.1(11) . . ? H16A C16 H16C 106.4(17) . . ? H16B C16 H16C 113.5(15) . . ? C14 C17 H17A 110.9(11) . . ? C14 C17 H17B 109.9(11) . . ? H17A C17 H17B 105.6(14) . . ? C14 C17 H17C 113.8(10) . . ? H17A C17 H17C 109.5(15) . . ? H17B C17 H17C 106.8(14) . . ? C2 N1 C6 123.36(11) . . ? C2 N1 C5 112.72(11) . . ? C6 N1 C5 123.55(11) . . ? C13 N2 C3 118.63(11) . . ? C13 N2 H2 119.2(10) . . ? C3 N2 H2 119.9(10) . . ? C8 O9 C9 121.77(11) . . ? C13 O14 C14 120.12(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 N2 35.20(18) . . . . ? N1 C2 C3 N2 -145.66(11) . . . . ? O2 C2 C3 C4 160.35(13) . . . . ? N1 C2 C3 C4 -20.52(14) . . . . ? N2 C3 C4 C5 154.79(12) . . . . ? C2 C3 C4 C5 33.25(15) . . . . ? C3 C4 C5 N1 -33.84(16) . . . . ? N1 C6 C8 O8 -3.4(2) . . . . ? C7 C6 C8 O8 121.56(16) . . . . ? N1 C6 C8 O9 176.12(11) . . . . ? C7 C6 C8 O9 -58.92(15) . . . . ? O2 C2 N1 C6 4.3(2) . . . . ? C3 C2 N1 C6 -174.81(12) . . . . ? O2 C2 N1 C5 177.53(13) . . . . ? C3 C2 N1 C5 -1.59(15) . . . . ? C7 C6 N1 C2 118.51(15) . . . . ? C8 C6 N1 C2 -117.00(13) . . . . ? C7 C6 N1 C5 -53.99(18) . . . . ? C8 C6 N1 C5 70.50(17) . . . . ? C4 C5 N1 C2 22.96(16) . . . . ? C4 C5 N1 C6 -163.83(12) . . . . ? O13 C13 N2 C3 -14.8(2) . . . . ? O14 C13 N2 C3 165.17(11) . . . . ? C2 C3 N2 C13 -173.18(11) . . . . ? C4 C3 N2 C13 69.67(16) . . . . ? O8 C8 O9 C9 -3.5(2) . . . . ? C6 C8 O9 C9 177.03(11) . . . . ? C12 C9 O9 C8 177.98(12) . . . . ? C11 C9 O9 C8 -64.06(16) . . . . ? C10 C9 O9 C8 60.60(17) . . . . ? O13 C13 O14 C14 0.05(19) . . . . ? N2 C13 O14 C14 -179.95(11) . . . . ? C16 C14 O14 C13 -66.20(15) . . . . ? C17 C14 O14 C13 58.33(15) . . . . ? C15 C14 O14 C13 175.73(11) . . . . ?