# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_gf324a _database_code_depnum_ccdc_archive 'CCDC 853618' #TrackingRef 'gf324-ms992.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-isopropyl-5-methylcyclohexyl-4-(tert-butoxycarbonylamino) -2-methyl-5-phenylpentanoate' ; _chemical_name_common ; '2-isopropyl-5-methylcyclohexyl-4-(tert-butoxycarbonylamino) - 2-methyl-5-phenylpentanoate' ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H43 N O4' _chemical_formula_sum 'C27 H43 N O4' _chemical_formula_weight 445.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 9.862(2) _cell_length_b 10.080(2) _cell_length_c 27.249(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2708.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 88 _cell_measurement_theta_min 6.48 _cell_measurement_theta_max 28.23 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type \q/2\q _diffrn_measurement_method 'Siemens P4 diffractometer' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 3316 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 64.99 _reflns_number_total 3101 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0797P)^2^+0.0967P] 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 SHELXL _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 3101 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.7277(2) -0.1438(2) 0.14408(7) 0.0540(6) Uani 1 1 d . . . O2 O 0.7399(3) 0.0452(2) 0.18708(9) 0.0746(8) Uani 1 1 d . . . O3 O 0.69956(19) 0.43434(17) 0.01222(8) 0.0477(5) Uani 1 1 d . . . O4 O 0.48991(19) 0.3398(2) 0.01276(8) 0.0519(5) Uani 1 1 d . . . N1 N 0.6828(3) 0.2193(2) 0.02036(9) 0.0396(5) Uani 1 1 d . . . H1N H 0.763(3) 0.221(3) 0.0207(10) 0.037(8) Uiso 1 1 d . . . C1 C 0.7025(3) -0.0154(3) 0.15171(10) 0.0471(7) Uani 1 1 d . . . C2 C 0.6199(4) 0.0453(3) 0.11030(11) 0.0490(8) Uani 1 1 d . . . H2 H 0.628(3) 0.141(4) 0.1137(12) 0.066(10) Uiso 1 1 d . . . C3 C 0.6704(3) 0.0020(3) 0.06006(10) 0.0427(7) Uani 1 1 d . . . H3A H 0.6416 -0.0886 0.0542 0.051 Uiso 1 1 calc R . . H3B H 0.7688 0.0030 0.0602 0.051 Uiso 1 1 calc R . . C4 C 0.6199(3) 0.0892(2) 0.01776(10) 0.0367(6) Uani 1 1 d . . . H4 H 0.523(3) 0.108(2) 0.0190(8) 0.025(6) Uiso 1 1 d . . . C5 C 0.6499(3) 0.0244(3) -0.03216(10) 0.0447(7) Uani 1 1 d . . . H5A H 0.7462 0.0054 -0.0342 0.054 Uiso 1 1 calc R . . H5B H 0.6017 -0.0593 -0.0341 0.054 Uiso 1 1 calc R . . C6 C 0.6103(3) 0.1087(3) -0.07488(10) 0.0433(7) Uani 1 1 d . . . C7 C 0.7064(4) 0.1723(4) -0.10271(12) 0.0739(11) Uani 1 1 d . . . H7 H 0.7979 0.1601 -0.0958 0.089 Uiso 1 1 calc R . . C8 C 0.6678(5) 0.2552(5) -0.14126(14) 0.0903(14) Uani 1 1 d . . . H8A H 0.7336 0.2973 -0.1601 0.108 Uiso 1 1 calc R . . C9 C 0.5333(5) 0.2748(4) -0.15157(12) 0.0740(11) Uani 1 1 d . . . H9 H 0.5081 0.3314 -0.1769 0.089 Uiso 1 1 calc R . . C10 C 0.4366(4) 0.2116(4) -0.12472(12) 0.0625(9) Uani 1 1 d . . . H10 H 0.3451 0.2238 -0.1318 0.075 Uiso 1 1 calc R . . C11 C 0.4762(3) 0.1285(3) -0.08669(11) 0.0521(8) Uani 1 1 d . . . H11 H 0.4099 0.0848 -0.0686 0.063 Uiso 1 1 calc R . . C12 C 0.6130(3) 0.3314(3) 0.01471(10) 0.0379(6) Uani 1 1 d . . . C13 C 0.6518(3) 0.5696(3) 0.00328(11) 0.0445(7) Uani 1 1 d . . . C14 C 0.7828(3) 0.6480(3) 0.00417(15) 0.0635(9) Uani 1 1 d . . . H14A H 0.8408 0.6183 -0.0219 0.095 Uiso 1 1 calc R . . H14B H 0.8274 0.6350 0.0351 0.095 Uiso 1 1 calc R . . H14C H 0.7631 0.7406 -0.0002 0.095 Uiso 1 1 calc R . . C15 C 0.5856(4) 0.5770(4) -0.04628(14) 0.0830(13) Uani 1 1 d . . . H15A H 0.6488 0.5488 -0.0710 0.125 Uiso 1 1 calc R . . H15B H 0.5582 0.6667 -0.0527 0.125 Uiso 1 1 calc R . . H15C H 0.5075 0.5202 -0.0468 0.125 Uiso 1 1 calc R . . C16 C 0.5581(4) 0.6146(3) 0.04404(16) 0.0730(11) Uani 1 1 d . . . H16A H 0.6041 0.6075 0.0750 0.110 Uiso 1 1 calc R . . H16B H 0.4786 0.5597 0.0444 0.110 Uiso 1 1 calc R . . H16C H 0.5323 0.7053 0.0386 0.110 Uiso 1 1 calc R . . C17 C 0.8111(3) -0.2131(3) 0.18056(10) 0.0485(7) Uani 1 1 d . . . H17 H 0.7941 -0.1748 0.2130 0.058 Uiso 1 1 calc R . . C18 C 0.9581(4) -0.1948(3) 0.16757(12) 0.0599(8) Uani 1 1 d . . . H18A H 0.9795 -0.1008 0.1679 0.072 Uiso 1 1 calc R . . H18B H 0.9734 -0.2273 0.1345 0.072 Uiso 1 1 calc R . . C19 C 1.0528(4) -0.2670(4) 0.20273(13) 0.0636(9) Uani 1 1 d . . . H19 H 1.0403 -0.2286 0.2355 0.076 Uiso 1 1 calc R . . C20 C 1.0128(4) -0.4117(4) 0.20519(14) 0.0678(10) Uani 1 1 d . . . H20A H 1.0663 -0.4554 0.2303 0.081 Uiso 1 1 calc R . . H20B H 1.0332 -0.4537 0.1740 0.081 Uiso 1 1 calc R . . C21 C 0.8638(4) -0.4305(4) 0.21657(12) 0.0611(9) Uani 1 1 d . . . H21A H 0.8461 -0.3992 0.2496 0.073 Uiso 1 1 calc R . . H21B H 0.8427 -0.5244 0.2156 0.073 Uiso 1 1 calc R . . C22 C 0.7696(3) -0.3568(3) 0.18079(11) 0.0512(8) Uani 1 1 d . . . H22 H 0.7884 -0.3918 0.1479 0.061 Uiso 1 1 calc R . . C23 C 0.6170(4) -0.3801(4) 0.19083(14) 0.0718(11) Uani 1 1 d . . . H23 H 0.5674 -0.3254 0.1671 0.086 Uiso 1 1 calc R . . C24 C 0.5735(4) -0.3333(8) 0.24168(17) 0.135(3) Uani 1 1 d . . . H24A H 0.6002 -0.2425 0.2462 0.203 Uiso 1 1 calc R . . H24B H 0.6162 -0.3875 0.2662 0.203 Uiso 1 1 calc R . . H24C H 0.4768 -0.3405 0.2447 0.203 Uiso 1 1 calc R . . C25 C 0.5767(6) -0.5230(5) 0.1808(3) 0.131(2) Uani 1 1 d . . . H25A H 0.4816 -0.5339 0.1870 0.196 Uiso 1 1 calc R . . H25B H 0.6274 -0.5809 0.2019 0.196 Uiso 1 1 calc R . . H25C H 0.5957 -0.5443 0.1472 0.196 Uiso 1 1 calc R . . C26 C 1.2009(4) -0.2493(6) 0.1884(2) 0.1135(18) Uani 1 1 d . . . H26A H 1.2224 -0.1564 0.1874 0.170 Uiso 1 1 calc R . . H26B H 1.2161 -0.2878 0.1567 0.170 Uiso 1 1 calc R . . H26C H 1.2576 -0.2925 0.2122 0.170 Uiso 1 1 calc R . . C27 C 0.4707(4) 0.0096(5) 0.11815(14) 0.0864(14) Uani 1 1 d . . . H27A H 0.4173 0.0460 0.0919 0.130 Uiso 1 1 calc R . . H27B H 0.4403 0.0457 0.1488 0.130 Uiso 1 1 calc R . . H27C H 0.4608 -0.0851 0.1186 0.130 Uiso 1 1 calc R . . 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 0.0738(15) 0.0439(11) 0.0444(10) 0.0057(9) -0.0145(10) 0.0097(12) O2 0.101(2) 0.0629(13) 0.0600(13) -0.0123(12) -0.0210(14) 0.0069(15) O3 0.0343(10) 0.0277(8) 0.0812(13) 0.0064(10) -0.0128(10) -0.0004(8) O4 0.0336(12) 0.0380(9) 0.0842(15) -0.0045(11) -0.0034(10) 0.0006(9) N1 0.0274(14) 0.0323(11) 0.0590(14) 0.0071(11) -0.0047(11) 0.0002(10) C1 0.0511(19) 0.0454(15) 0.0448(15) 0.0019(13) 0.0003(14) 0.0016(15) C2 0.057(2) 0.0433(16) 0.0465(15) 0.0014(13) -0.0039(14) 0.0140(16) C3 0.0447(17) 0.0348(13) 0.0485(15) 0.0076(12) 0.0015(13) 0.0060(13) C4 0.0371(16) 0.0260(12) 0.0469(15) 0.0052(11) -0.0011(13) 0.0000(12) C5 0.0474(17) 0.0374(14) 0.0492(15) -0.0004(12) 0.0041(13) 0.0059(14) C6 0.0469(18) 0.0423(14) 0.0408(14) -0.0006(12) 0.0055(13) -0.0012(14) C7 0.058(2) 0.106(3) 0.0573(18) 0.021(2) 0.0002(17) -0.023(2) C8 0.091(3) 0.115(4) 0.065(2) 0.036(2) 0.004(2) -0.042(3) C9 0.105(3) 0.073(2) 0.0441(16) 0.0100(17) -0.008(2) -0.008(3) C10 0.065(2) 0.069(2) 0.0539(17) 0.0000(18) -0.0036(17) 0.016(2) C11 0.049(2) 0.0548(18) 0.0525(16) 0.0061(14) 0.0082(14) 0.0060(16) C12 0.0333(17) 0.0321(12) 0.0482(14) -0.0004(12) -0.0047(12) -0.0013(12) C13 0.0396(15) 0.0293(12) 0.0646(17) 0.0065(13) -0.0077(13) 0.0035(13) C14 0.0491(18) 0.0354(14) 0.106(3) 0.0093(17) 0.0010(19) -0.0039(15) C15 0.089(3) 0.079(2) 0.081(3) 0.024(2) -0.035(2) -0.001(3) C16 0.062(2) 0.0513(18) 0.105(3) -0.0166(19) 0.014(2) -0.0011(18) C17 0.0548(19) 0.0536(16) 0.0372(13) 0.0055(13) -0.0090(14) 0.0061(16) C18 0.065(2) 0.0575(19) 0.0573(18) 0.0100(15) 0.0004(17) -0.0055(18) C19 0.054(2) 0.075(2) 0.0617(19) 0.0029(18) -0.0084(17) 0.004(2) C20 0.071(3) 0.067(2) 0.064(2) 0.0034(18) -0.0150(18) 0.016(2) C21 0.067(2) 0.0605(19) 0.0557(18) 0.0158(16) -0.0141(16) 0.003(2) C22 0.059(2) 0.0502(16) 0.0444(15) 0.0108(14) -0.0128(14) 0.0003(16) C23 0.059(2) 0.089(3) 0.068(2) 0.024(2) -0.0139(18) -0.011(2) C24 0.066(3) 0.262(8) 0.079(3) 0.009(4) 0.018(2) -0.010(5) C25 0.107(4) 0.101(4) 0.184(5) 0.058(4) -0.038(4) -0.050(3) C26 0.057(3) 0.147(5) 0.137(4) 0.003(4) -0.006(3) -0.004(3) C27 0.054(2) 0.139(4) 0.065(2) 0.011(3) 0.0083(18) 0.021(3) _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 O1 C1 1.335(4) . ? O1 C17 1.467(3) . ? O2 C1 1.199(3) . ? O3 C12 1.345(3) . ? O3 C13 1.463(3) . ? O4 C12 1.218(3) . ? N1 C12 1.332(3) . ? N1 C4 1.452(3) . ? N1 H1N 0.79(3) . ? C1 C2 1.520(4) . ? C2 C3 1.521(4) . ? C2 C27 1.530(5) . ? C2 H2 0.98(4) . ? C3 C4 1.532(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.538(4) . ? C4 H4 0.98(3) . ? C5 C6 1.493(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.373(4) . ? C6 C11 1.376(4) . ? C7 C8 1.395(5) . ? C7 H7 0.9300 . ? C8 C9 1.370(6) . ? C8 H8A 0.9300 . ? C9 C10 1.361(5) . ? C9 H9 0.9300 . ? C10 C11 1.388(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C15 1.502(5) . ? C13 C16 1.514(5) . ? C13 C14 1.515(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.504(5) . ? C17 C22 1.505(4) . ? C17 H17 0.9800 . ? C18 C19 1.523(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.513(5) . ? C19 C26 1.522(6) . ? C19 H19 0.9800 . ? C20 C21 1.514(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.538(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.547(5) . ? C22 H22 0.9800 . ? C23 C25 1.519(6) . ? C23 C24 1.525(6) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 C1 O1 C17 117.4(2) . . ? C12 O3 C13 121.5(2) . . ? C12 N1 C4 122.7(2) . . ? C12 N1 H1N 120(2) . . ? C4 N1 H1N 116(2) . . ? O2 C1 O1 124.2(3) . . ? O2 C1 C2 123.8(3) . . ? O1 C1 C2 112.0(2) . . ? C1 C2 C3 112.2(2) . . ? C1 C2 C27 108.5(3) . . ? C3 C2 C27 111.9(3) . . ? C1 C2 H2 106(2) . . ? C3 C2 H2 110(2) . . ? C27 C2 H2 108(2) . . ? C2 C3 C4 113.9(2) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N1 C4 C3 110.0(2) . . ? N1 C4 C5 110.1(2) . . ? C3 C4 C5 111.1(2) . . ? N1 C4 H4 103.9(14) . . ? C3 C4 H4 113.9(14) . . ? C5 C4 H4 107.6(14) . . ? C6 C5 C4 113.5(2) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C11 117.8(3) . . ? C7 C6 C5 121.1(3) . . ? C11 C6 C5 121.1(3) . . ? C6 C7 C8 120.5(4) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.4(4) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 119.1(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C6 C11 C10 122.2(3) . . ? C6 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? O4 C12 N1 125.4(3) . . ? O4 C12 O3 125.2(3) . . ? N1 C12 O3 109.4(2) . . ? O3 C13 C15 109.6(3) . . ? O3 C13 C16 110.7(3) . . ? C15 C13 C16 112.3(3) . . ? O3 C13 C14 102.1(2) . . ? C15 C13 C14 111.0(3) . . ? C16 C13 C14 110.6(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 C18 108.8(2) . . ? O1 C17 C22 108.0(2) . . ? C18 C17 C22 112.4(3) . . ? O1 C17 H17 109.2 . . ? C18 C17 H17 109.2 . . ? C22 C17 H17 109.2 . . ? C17 C18 C19 112.6(3) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C26 112.0(4) . . ? C20 C19 C18 109.2(3) . . ? C26 C19 C18 111.8(3) . . ? C20 C19 H19 107.9 . . ? C26 C19 H19 107.9 . . ? C18 C19 H19 107.9 . . ? C19 C20 C21 112.5(3) . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 C22 113.3(3) . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C17 C22 C21 107.6(3) . . ? C17 C22 C23 114.3(3) . . ? C21 C22 C23 113.7(3) . . ? C17 C22 H22 106.9 . . ? C21 C22 H22 106.9 . . ? C23 C22 H22 106.9 . . ? C25 C23 C24 112.5(5) . . ? C25 C23 C22 111.5(4) . . ? C24 C23 C22 112.8(3) . . ? C25 C23 H23 106.5 . . ? C24 C23 H23 106.5 . . ? C22 C23 H23 106.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C2 C27 H27A 109.5 . . ? C2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C17 O1 C1 O2 -2.5(5) . . . . ? C17 O1 C1 C2 177.8(2) . . . . ? O2 C1 C2 C3 136.6(3) . . . . ? O1 C1 C2 C3 -43.7(4) . . . . ? O2 C1 C2 C27 -99.3(4) . . . . ? O1 C1 C2 C27 80.5(4) . . . . ? C1 C2 C3 C4 -163.1(3) . . . . ? C27 C2 C3 C4 74.7(4) . . . . ? C12 N1 C4 C3 -134.7(3) . . . . ? C12 N1 C4 C5 102.5(3) . . . . ? C2 C3 C4 N1 69.4(3) . . . . ? C2 C3 C4 C5 -168.4(3) . . . . ? N1 C4 C5 C6 -54.4(3) . . . . ? C3 C4 C5 C6 -176.6(3) . . . . ? C4 C5 C6 C7 106.1(3) . . . . ? C4 C5 C6 C11 -71.8(4) . . . . ? C11 C6 C7 C8 0.6(5) . . . . ? C5 C6 C7 C8 -177.3(3) . . . . ? C6 C7 C8 C9 0.5(7) . . . . ? C7 C8 C9 C10 -1.1(7) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C7 C6 C11 C10 -1.2(5) . . . . ? C5 C6 C11 C10 176.8(3) . . . . ? C9 C10 C11 C6 0.5(5) . . . . ? C4 N1 C12 O4 9.3(5) . . . . ? C4 N1 C12 O3 -171.6(3) . . . . ? C13 O3 C12 O4 -4.4(4) . . . . ? C13 O3 C12 N1 176.5(2) . . . . ? C12 O3 C13 C15 -62.7(4) . . . . ? C12 O3 C13 C16 61.7(3) . . . . ? C12 O3 C13 C14 179.5(3) . . . . ? C1 O1 C17 C18 -86.5(3) . . . . ? C1 O1 C17 C22 151.2(3) . . . . ? O1 C17 C18 C19 -178.3(3) . . . . ? C22 C17 C18 C19 -58.8(4) . . . . ? C17 C18 C19 C20 54.5(4) . . . . ? C17 C18 C19 C26 179.0(4) . . . . ? C26 C19 C20 C21 -176.8(3) . . . . ? C18 C19 C20 C21 -52.4(4) . . . . ? C19 C20 C21 C22 54.9(4) . . . . ? O1 C17 C22 C21 176.3(2) . . . . ? C18 C17 C22 C21 56.3(3) . . . . ? O1 C17 C22 C23 -56.4(3) . . . . ? C18 C17 C22 C23 -176.4(3) . . . . ? C20 C21 C22 C17 -54.8(4) . . . . ? C20 C21 C22 C23 177.6(3) . . . . ? C17 C22 C23 C25 168.9(4) . . . . ? C21 C22 C23 C25 -67.0(5) . . . . ? C17 C22 C23 C24 -63.4(5) . . . . ? C21 C22 C23 C24 60.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.172 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041 data_ms992 _database_code_depnum_ccdc_archive 'CCDC 853619' #TrackingRef 'gf324-ms992.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Ethyl 2-(3-(tert-butoxycarbonylamino)-4-methylpentanoyl) thiazole-4-carboxylate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H28 N2 O5 S' _chemical_formula_sum 'C17 H28 N2 O5 S' _chemical_formula_weight 372.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.756(5) _cell_length_b 15.696(5) _cell_length_c 10.018(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 98.510(5) _cell_angle_gamma 90.000(5) _cell_volume 1983.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 66 _cell_measurement_theta_min 5.73 _cell_measurement_theta_max 30.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 1.690 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.2966 _exptl_absorpt_correction_T_max 0.9054 _exptl_absorpt_process_details '(XSCANS, Siemens 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 6420 _diffrn_reflns_av_R_equivalents 0.1023 _diffrn_reflns_av_sigmaI/netI 0.0971 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 65.00 _reflns_number_total 3233 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0611P)^2^+0.3346P] 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 SHELXL _refine_ls_extinction_coef 0.0016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3233 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.001 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 S S 0.70862(7) 0.09334(6) 0.78561(8) 0.0517(3) Uani 1 1 d . . . O1 O 0.8424(2) 0.21530(18) 0.9204(2) 0.0489(6) Uani 1 1 d . . . H1O H 0.826(4) 0.270(4) 0.942(4) 0.059 Uiso 0.80(8) 1 d P A 1 H1O' H 0.788(18) 0.219(13) 0.952(19) 0.059 Uiso 0.20(8) 1 d P A 2 O2 O 0.5947(2) 0.01626(19) 0.3525(3) 0.0783(8) Uani 1 1 d . . . O3 O 0.73827(19) 0.08769(15) 0.3129(2) 0.0604(7) Uani 1 1 d . . . O4 O 1.20704(17) 0.26307(17) 1.0719(2) 0.0590(7) Uani 1 1 d . . . O5 O 1.31928(16) 0.21980(15) 0.92922(18) 0.0498(6) Uani 1 1 d . . . N1 N 0.77294(18) 0.14980(14) 0.5724(2) 0.0382(6) Uani 1 1 d . . . N2 N 1.15480(18) 0.25308(17) 0.8459(2) 0.0416(6) Uani 1 1 d . . . H2N H 1.181(3) 0.244(2) 0.768(3) 0.053(9) Uiso 1 1 d . . . C1 C 1.0449(2) 0.27866(19) 0.8485(3) 0.0395(7) Uani 1 1 d . . . H1 H 1.029(2) 0.2742(17) 0.942(3) 0.038(7) Uiso 1 1 d . . . C2 C 0.9720(2) 0.21367(18) 0.7671(3) 0.0385(6) Uani 1 1 d . . . H2B H 0.9792 0.2189 0.6724 0.046 Uiso 1 1 calc R . . H2C H 0.9944 0.1567 0.7961 0.046 Uiso 1 1 calc R . . C3 C 0.8557(2) 0.22504(18) 0.7827(3) 0.0387(6) Uani 1 1 d . . . H3 H 0.827(2) 0.2845(18) 0.749(3) 0.037(7) Uiso 1 1 d . . . C4 C 0.7850(2) 0.15997(17) 0.7036(3) 0.0362(6) Uani 1 1 d . . . C5 C 1.0249(3) 0.3715(2) 0.8084(3) 0.0489(8) Uani 1 1 d . . . H5 H 0.954(3) 0.3845(19) 0.815(3) 0.046(8) Uiso 1 1 d . . . C6 C 1.0412(4) 0.3910(2) 0.6646(4) 0.0735(11) Uani 1 1 d . . . H6A H 0.9983 0.3534 0.6037 0.110 Uiso 1 1 calc R . . H6B H 1.1145 0.3831 0.6558 0.110 Uiso 1 1 calc R . . H6C H 1.0212 0.4490 0.6433 0.110 Uiso 1 1 calc R . . C7 C 1.0912(3) 0.4311(3) 0.9071(4) 0.0764(12) Uani 1 1 d . . . H7A H 1.0794 0.4183 0.9974 0.115 Uiso 1 1 calc R . . H7B H 1.0711 0.4890 0.8858 0.115 Uiso 1 1 calc R . . H7C H 1.1649 0.4236 0.9002 0.115 Uiso 1 1 calc R . . C8 C 0.6564(2) 0.0507(2) 0.6355(3) 0.0496(8) Uani 1 1 d . . . H8 H 0.6052 0.0080 0.6247 0.059 Uiso 1 1 calc R . . C9 C 0.6987(2) 0.08656(18) 0.5331(3) 0.0392(6) Uani 1 1 d . . . C10 C 0.6704(2) 0.0602(2) 0.3914(3) 0.0484(8) Uani 1 1 d . . . C11 C 0.7279(3) 0.0528(3) 0.1761(3) 0.0737(12) Uani 1 1 d . . . H11A H 0.7540 0.0938 0.1165 0.088 Uiso 1 1 calc R . . H11B H 0.6538 0.0419 0.1429 0.088 Uiso 1 1 calc R . . C12 C 0.7885(4) -0.0269(3) 0.1757(4) 0.0903(14) Uani 1 1 d . . . H12A H 0.7810 -0.0493 0.0856 0.135 Uiso 1 1 calc R . . H12B H 0.7621 -0.0677 0.2340 0.135 Uiso 1 1 calc R . . H12C H 0.8620 -0.0159 0.2074 0.135 Uiso 1 1 calc R . . C13 C 1.2254(2) 0.24692(19) 0.9588(3) 0.0390(6) Uani 1 1 d . . . C14 C 1.4121(3) 0.2156(3) 1.0359(3) 0.0566(9) Uani 1 1 d . . . C15 C 1.4981(3) 0.1862(4) 0.9575(4) 0.1027(18) Uani 1 1 d . . . H15A H 1.4820 0.1299 0.9231 0.154 Uiso 1 1 calc R . . H15B H 1.5649 0.1856 1.0159 0.154 Uiso 1 1 calc R . . H15C H 1.5021 0.2245 0.8837 0.154 Uiso 1 1 calc R . . C16 C 1.3943(3) 0.1522(3) 1.1437(4) 0.0790(12) Uani 1 1 d . . . H16A H 1.3801 0.0971 1.1035 0.119 Uiso 1 1 calc R . . H16B H 1.3349 0.1699 1.1856 0.119 Uiso 1 1 calc R . . H16C H 1.4565 0.1493 1.2104 0.119 Uiso 1 1 calc R . . C17 C 1.4366(3) 0.3035(3) 1.0917(4) 0.0877(15) Uani 1 1 d . . . H17A H 1.3813 0.3215 1.1408 0.132 Uiso 1 1 calc R . . H17B H 1.4411 0.3424 1.0188 0.132 Uiso 1 1 calc R . . H17C H 1.5029 0.3026 1.1511 0.132 Uiso 1 1 calc R . . 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 S 0.0514(5) 0.0632(5) 0.0433(5) 0.0056(3) 0.0156(4) -0.0102(4) O1 0.0552(15) 0.0592(16) 0.0350(12) -0.0060(10) 0.0153(10) 0.0018(11) O2 0.0657(18) 0.097(2) 0.0680(16) -0.0099(14) -0.0058(13) -0.0368(15) O3 0.0653(15) 0.0764(17) 0.0394(12) -0.0101(10) 0.0077(11) -0.0239(13) O4 0.0493(13) 0.100(2) 0.0281(11) -0.0023(10) 0.0083(10) -0.0014(12) O5 0.0382(11) 0.0789(15) 0.0312(10) -0.0029(10) 0.0017(9) 0.0071(10) N1 0.0375(13) 0.0410(13) 0.0353(13) 0.0018(10) 0.0025(10) -0.0026(10) N2 0.0328(12) 0.0647(16) 0.0273(12) -0.0045(11) 0.0050(10) 0.0018(12) C1 0.0346(15) 0.0521(17) 0.0333(15) -0.0056(12) 0.0098(12) -0.0012(13) C2 0.0378(15) 0.0464(16) 0.0322(14) -0.0059(12) 0.0078(12) -0.0001(12) C3 0.0421(16) 0.0424(16) 0.0324(15) -0.0013(12) 0.0083(12) 0.0016(12) C4 0.0342(14) 0.0397(15) 0.0349(15) 0.0022(11) 0.0059(11) 0.0028(12) C5 0.0420(18) 0.0471(18) 0.058(2) -0.0082(14) 0.0091(15) -0.0008(14) C6 0.090(3) 0.060(2) 0.070(2) 0.0141(18) 0.011(2) 0.008(2) C7 0.078(3) 0.058(2) 0.090(3) -0.023(2) 0.004(2) -0.012(2) C8 0.0422(17) 0.0546(19) 0.0521(19) 0.0031(14) 0.0077(14) -0.0110(14) C9 0.0348(15) 0.0420(16) 0.0405(16) 0.0021(12) 0.0044(12) -0.0008(12) C10 0.0396(16) 0.0566(19) 0.0469(18) 0.0019(14) -0.0003(14) -0.0042(14) C11 0.092(3) 0.089(3) 0.0379(19) -0.0146(18) 0.0032(19) -0.018(2) C12 0.102(4) 0.085(3) 0.083(3) -0.031(2) 0.010(3) -0.005(3) C13 0.0375(15) 0.0506(16) 0.0300(15) 0.0017(12) 0.0089(12) -0.0027(13) C14 0.0384(17) 0.092(3) 0.0355(16) 0.0071(16) -0.0082(13) 0.0070(17) C15 0.050(2) 0.194(6) 0.063(3) 0.011(3) 0.004(2) 0.037(3) C16 0.081(3) 0.089(3) 0.060(2) 0.021(2) -0.010(2) 0.010(2) C17 0.074(3) 0.107(4) 0.075(3) 0.002(2) -0.014(2) -0.038(3) _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 S C8 1.691(3) . ? S C4 1.719(3) . ? O1 C3 1.423(3) . ? O2 C10 1.204(4) . ? O3 C10 1.324(4) . ? O3 C11 1.464(4) . ? O4 C13 1.218(3) . ? O5 C13 1.345(3) . ? O5 C14 1.474(3) . ? N1 C4 1.310(3) . ? N1 C9 1.388(3) . ? N2 C13 1.341(3) . ? N2 C1 1.462(4) . ? C1 C5 1.522(4) . ? C1 C2 1.532(4) . ? C2 C3 1.525(4) . ? C3 C4 1.508(4) . ? C5 C6 1.517(5) . ? C5 C7 1.524(4) . ? C8 C9 1.351(4) . ? C9 C10 1.471(4) . ? C11 C12 1.471(5) . ? C14 C17 1.503(6) . ? C14 C16 1.510(5) . ? C14 C15 1.514(5) . ? 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 C8 S C4 89.56(14) . . ? C10 O3 C11 117.2(3) . . ? C13 O5 C14 120.0(2) . . ? C4 N1 C9 110.2(2) . . ? C13 N2 C1 122.1(2) . . ? N2 C1 C5 112.4(3) . . ? N2 C1 C2 108.4(2) . . ? C5 C1 C2 115.6(2) . . ? C3 C2 C1 113.0(2) . . ? O1 C3 C4 106.8(2) . . ? O1 C3 C2 110.1(2) . . ? C4 C3 C2 112.5(2) . . ? N1 C4 C3 125.6(3) . . ? N1 C4 S 114.5(2) . . ? C3 C4 S 119.9(2) . . ? C6 C5 C1 113.8(3) . . ? C6 C5 C7 110.5(3) . . ? C1 C5 C7 111.2(3) . . ? C9 C8 S 111.1(2) . . ? C8 C9 N1 114.5(3) . . ? C8 C9 C10 123.2(3) . . ? N1 C9 C10 122.3(3) . . ? O2 C10 O3 123.9(3) . . ? O2 C10 C9 122.9(3) . . ? O3 C10 C9 113.1(3) . . ? O3 C11 C12 110.2(3) . . ? O4 C13 N2 124.9(3) . . ? O4 C13 O5 124.8(3) . . ? N2 C13 O5 110.2(2) . . ? O5 C14 C17 109.2(3) . . ? O5 C14 C16 111.0(3) . . ? C17 C14 C16 112.6(3) . . ? O5 C14 C15 101.7(3) . . ? C17 C14 C15 110.2(4) . . ? C16 C14 C15 111.5(4) . . ? 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 C13 N2 C1 C5 101.4(3) . . . . ? C13 N2 C1 C2 -129.6(3) . . . . ? N2 C1 C2 C3 170.1(2) . . . . ? C5 C1 C2 C3 -62.7(3) . . . . ? C1 C2 C3 O1 -60.2(3) . . . . ? C1 C2 C3 C4 -179.2(2) . . . . ? C9 N1 C4 C3 -177.6(2) . . . . ? C9 N1 C4 S 0.6(3) . . . . ? O1 C3 C4 N1 178.4(3) . . . . ? C2 C3 C4 N1 -60.7(4) . . . . ? O1 C3 C4 S 0.3(3) . . . . ? C2 C3 C4 S 121.3(2) . . . . ? C8 S C4 N1 -0.9(2) . . . . ? C8 S C4 C3 177.4(2) . . . . ? N2 C1 C5 C6 63.2(4) . . . . ? C2 C1 C5 C6 -62.0(4) . . . . ? N2 C1 C5 C7 -62.4(3) . . . . ? C2 C1 C5 C7 172.4(3) . . . . ? C4 S C8 C9 0.9(3) . . . . ? S C8 C9 N1 -0.8(4) . . . . ? S C8 C9 C10 178.2(2) . . . . ? C4 N1 C9 C8 0.1(4) . . . . ? C4 N1 C9 C10 -178.8(3) . . . . ? C11 O3 C10 O2 -8.6(5) . . . . ? C11 O3 C10 C9 169.6(3) . . . . ? C8 C9 C10 O2 13.8(5) . . . . ? N1 C9 C10 O2 -167.3(3) . . . . ? C8 C9 C10 O3 -164.3(3) . . . . ? N1 C9 C10 O3 14.5(4) . . . . ? C10 O3 C11 C12 -87.0(4) . . . . ? C1 N2 C13 O4 -1.5(5) . . . . ? C1 N2 C13 O5 178.1(3) . . . . ? C14 O5 C13 O4 -6.0(5) . . . . ? C14 O5 C13 N2 174.4(3) . . . . ? C13 O5 C14 C17 -61.2(4) . . . . ? C13 O5 C14 C16 63.5(4) . . . . ? C13 O5 C14 C15 -177.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1 0.91(6) 2.01(5) 2.826(3) 149(4) 4_566 N2 H2N O4 0.90(4) 2.05(4) 2.930(3) 166(3) 4_565 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.291 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.050