# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_anudgleu _database_code_depnum_ccdc_archive 'CCDC 802255' #TrackingRef 'Boc-dgLeu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(S,E)-ethyl 4-(tert-butoxycarbonylamino)-6-methylhept-2-enoate' _chemical_name_common '(S,E)-ethyl 4-(tert-butoxycarbonylamino)-6-methylhept-2-enoate' _chemical_formula_moiety 'C30 H54 N2 O8' _chemical_formula_sum 'C30 H54 N2 O8' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method Methanol _chemical_melting_point ? _exptl_crystal_description 'Retangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 296(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 570.75 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.340(3) _cell_length_b 9.733(3) _cell_length_c 18.073(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.331(5) _cell_angle_gamma 90.00 _cell_volume 1745.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite Monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6755 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 24.28 _reflns_number_total 2788 _reflns_number_gt 2413 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0504P)^2^+0.1961P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(13) _refine_ls_number_reflns 2788 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.004 _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 O1 O 0.7778(2) 0.7444(2) 0.04948(13) 0.0539(7) Uani 1 1 d . . . O2 O 0.6406(3) 0.9322(3) 0.02612(15) 0.0640(8) Uani 1 1 d . . . O3 O 0.8851(2) 1.2986(3) -0.14578(13) 0.0583(7) Uani 1 1 d . . . O4 O 0.8935(3) 1.0896(3) -0.19697(15) 0.0681(8) Uani 1 1 d . . . O5 O 0.7330(2) 0.0041(2) 0.46498(12) 0.0502(7) Uani 1 1 d . . . O6 O 0.8562(3) 0.1951(3) 0.51297(15) 0.0622(8) Uani 1 1 d . . . O7 O 0.5688(2) 0.5365(3) 0.65936(13) 0.0549(7) Uani 1 1 d . . . O8 O 0.5622(2) 0.3225(3) 0.70562(13) 0.0570(7) Uani 1 1 d . . . N1 N 0.8674(3) 0.9524(3) 0.06586(16) 0.0480(8) Uani 1 1 d . . . H1 H 0.9425 0.9082 0.0785 0.058 Uiso 1 1 calc R . . N2 N 0.6337(3) 0.2078(3) 0.44880(15) 0.0434(7) Uani 1 1 d . . . H2 H 0.5615 0.1616 0.4286 0.052 Uiso 1 1 calc R . . C1 C 0.6663(4) 0.6451(4) 0.0267(2) 0.0522(10) Uani 1 1 d . . . C2 C 0.7399(5) 0.5081(4) 0.0387(3) 0.0932(16) Uani 1 1 d . . . H2A H 0.8036 0.5059 0.0089 0.140 Uiso 1 1 calc R . . H2B H 0.6760 0.4349 0.0224 0.140 Uiso 1 1 calc R . . H2C H 0.7867 0.4969 0.0923 0.140 Uiso 1 1 calc R . . C3 C 0.5756(4) 0.6571(4) 0.0788(2) 0.0661(12) Uani 1 1 d . . . H3A H 0.6289 0.6525 0.1316 0.099 Uiso 1 1 calc R . . H3B H 0.5116 0.5831 0.0683 0.099 Uiso 1 1 calc R . . H3C H 0.5285 0.7432 0.0696 0.099 Uiso 1 1 calc R . . C4 C 0.5890(4) 0.6645(5) -0.0569(2) 0.0781(14) Uani 1 1 d . . . H4A H 0.5438 0.7517 -0.0633 0.117 Uiso 1 1 calc R . . H4B H 0.5238 0.5923 -0.0726 0.117 Uiso 1 1 calc R . . H4C H 0.6503 0.6619 -0.0881 0.117 Uiso 1 1 calc R . . C5 C 0.7504(4) 0.8807(4) 0.0451(2) 0.0463(10) Uani 1 1 d . . . C6 C 0.8698(4) 1.1014(3) 0.0674(2) 0.0460(10) Uani 1 1 d . . . H6 H 0.7866 1.1331 0.0777 0.055 Uiso 1 1 calc R . . C7 C 0.9890(4) 1.1503(4) 0.13381(19) 0.0527(10) Uani 1 1 d . . . H7A H 1.0705 1.1065 0.1290 0.063 Uiso 1 1 calc R . . H7B H 0.9996 1.2486 0.1288 0.063 Uiso 1 1 calc R . . C8 C 0.9748(4) 1.1206(4) 0.2138(2) 0.0588(11) Uani 1 1 d . . . H8 H 0.9473 1.0245 0.2152 0.071 Uiso 1 1 calc R . . C9 C 0.8685(5) 1.2109(5) 0.2330(2) 0.0828(14) Uani 1 1 d . . . H9A H 0.8917 1.3058 0.2298 0.124 Uiso 1 1 calc R . . H9B H 0.8645 1.1909 0.2843 0.124 Uiso 1 1 calc R . . H9C H 0.7824 1.1930 0.1970 0.124 Uiso 1 1 calc R . . C10 C 1.1094(5) 1.1398(7) 0.2744(2) 0.1075(19) Uani 1 1 d . . . H10A H 1.1739 1.0763 0.2648 0.161 Uiso 1 1 calc R . . H10B H 1.0985 1.1230 0.3246 0.161 Uiso 1 1 calc R . . H10C H 1.1406 1.2321 0.2719 0.161 Uiso 1 1 calc R . . C11 C 0.8757(3) 1.1624(4) -0.00748(19) 0.0489(10) Uani 1 1 d . . . H11 H 0.8765 1.2578 -0.0095 0.059 Uiso 1 1 calc R . . C12 C 0.8799(3) 1.0980(4) -0.0712(2) 0.0495(10) Uani 1 1 d . . . H12 H 0.8785 1.0025 -0.0724 0.059 Uiso 1 1 calc R . . C13 C 0.8866(4) 1.1738(5) -0.1399(2) 0.0511(10) Uani 1 1 d . . . C14 C 0.8997(5) 1.1536(5) -0.2696(2) 0.0763(13) Uani 1 1 d . . . H14A H 0.8504 1.2396 -0.2773 0.092 Uiso 1 1 calc R . . H14B H 0.8586 1.0933 -0.3126 0.092 Uiso 1 1 calc R . . C15 C 1.0421(4) 1.1791(5) -0.2667(2) 0.0802(14) Uani 1 1 d . . . H15A H 1.0810 1.2423 -0.2257 0.120 Uiso 1 1 calc R . . H15B H 1.0465 1.2175 -0.3148 0.120 Uiso 1 1 calc R . . H15C H 1.0911 1.0941 -0.2576 0.120 Uiso 1 1 calc R . . C16 C 0.8506(3) -0.0881(4) 0.47744(18) 0.0440(9) Uani 1 1 d . . . C17 C 0.9292(4) -0.0920(4) 0.56240(19) 0.0600(11) Uani 1 1 d . . . H17A H 0.9734 -0.0054 0.5770 0.090 Uiso 1 1 calc R . . H17B H 0.9954 -0.1639 0.5709 0.090 Uiso 1 1 calc R . . H17C H 0.8684 -0.1092 0.5929 0.090 Uiso 1 1 calc R . . C18 C 0.7855(4) -0.2269(4) 0.4519(2) 0.0620(11) Uani 1 1 d . . . H18A H 0.7299 -0.2522 0.4843 0.093 Uiso 1 1 calc R . . H18B H 0.8543 -0.2950 0.4560 0.093 Uiso 1 1 calc R . . H18C H 0.7310 -0.2210 0.3993 0.093 Uiso 1 1 calc R . . C19 C 0.9369(4) -0.0431(4) 0.42729(18) 0.0553(11) Uani 1 1 d . . . H19A H 0.8827 -0.0374 0.3747 0.083 Uiso 1 1 calc R . . H19B H 1.0080 -0.1085 0.4312 0.083 Uiso 1 1 calc R . . H19C H 0.9751 0.0454 0.4440 0.083 Uiso 1 1 calc R . . C20 C 0.7506(4) 0.1405(4) 0.4785(2) 0.0456(9) Uani 1 1 d . . . C21 C 0.6269(4) 0.3572(3) 0.45010(19) 0.0428(9) Uani 1 1 d . . . H21 H 0.7123 0.3928 0.4445 0.051 Uiso 1 1 calc R . . C22 C 0.5139(4) 0.4074(4) 0.38061(18) 0.0474(9) Uani 1 1 d . . . H22A H 0.4309 0.3619 0.3816 0.057 Uiso 1 1 calc R . . H22B H 0.5015 0.5051 0.3867 0.057 Uiso 1 1 calc R . . C23 C 0.5358(4) 0.3837(4) 0.3018(2) 0.0546(10) Uani 1 1 d . . . H23 H 0.5539 0.2859 0.2968 0.066 Uiso 1 1 calc R . . C24 C 0.6547(4) 0.4654(5) 0.2920(2) 0.0764(13) Uani 1 1 d . . . H24A H 0.6400 0.5615 0.2986 0.115 Uiso 1 1 calc R . . H24B H 0.6641 0.4500 0.2413 0.115 Uiso 1 1 calc R . . H24C H 0.7354 0.4365 0.3298 0.115 Uiso 1 1 calc R . . C25 C 0.4097(5) 0.4230(6) 0.2379(2) 0.0863(15) Uani 1 1 d . . . H25A H 0.3341 0.3714 0.2439 0.129 Uiso 1 1 calc R . . H25B H 0.4233 0.4028 0.1887 0.129 Uiso 1 1 calc R . . H25C H 0.3924 0.5194 0.2411 0.129 Uiso 1 1 calc R . . C26 C 0.6092(3) 0.4131(4) 0.52406(19) 0.0466(9) Uani 1 1 d . . . H26 H 0.6100 0.5083 0.5286 0.056 Uiso 1 1 calc R . . C27 C 0.5925(3) 0.3432(4) 0.58356(19) 0.0448(9) Uani 1 1 d . . . H27 H 0.5929 0.2476 0.5822 0.054 Uiso 1 1 calc R . . C28 C 0.5735(3) 0.4137(5) 0.6518(2) 0.0464(9) Uani 1 1 d . . . C29 C 0.5445(4) 0.3812(5) 0.7764(2) 0.0652(12) Uani 1 1 d . . . H29A H 0.6005 0.4624 0.7902 0.078 Uiso 1 1 calc R . . H29B H 0.5734 0.3151 0.8179 0.078 Uiso 1 1 calc R . . C30 C 0.4000(4) 0.4192(5) 0.7669(2) 0.0656(11) Uani 1 1 d . . . H30A H 0.3744 0.4924 0.7300 0.098 Uiso 1 1 calc R . . H30B H 0.3897 0.4489 0.8156 0.098 Uiso 1 1 calc R . . H30C H 0.3436 0.3408 0.7490 0.098 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 0.0466(16) 0.0302(17) 0.0823(18) -0.0009(12) 0.0139(13) -0.0024(13) O2 0.0419(17) 0.0445(18) 0.099(2) 0.0046(15) 0.0098(14) 0.0091(15) O3 0.0591(17) 0.0479(19) 0.0641(17) -0.0001(14) 0.0111(13) -0.0012(15) O4 0.082(2) 0.0630(18) 0.0671(18) -0.0206(16) 0.0339(15) -0.0182(16) O5 0.0444(16) 0.0292(17) 0.0741(17) -0.0051(12) 0.0122(13) 0.0031(13) O6 0.0453(17) 0.0381(17) 0.096(2) -0.0156(15) 0.0081(15) -0.0055(15) O7 0.0604(17) 0.0414(19) 0.0595(16) -0.0077(13) 0.0113(13) 0.0009(14) O8 0.0695(18) 0.0516(18) 0.0537(15) 0.0083(14) 0.0236(13) 0.0107(14) N1 0.0411(19) 0.028(2) 0.074(2) -0.0002(15) 0.0149(16) 0.0023(16) N2 0.0389(18) 0.0247(18) 0.067(2) -0.0007(15) 0.0161(15) 0.0028(16) C1 0.057(3) 0.038(2) 0.063(3) -0.004(2) 0.017(2) -0.013(2) C2 0.090(4) 0.036(3) 0.154(5) -0.009(3) 0.036(3) -0.012(3) C3 0.074(3) 0.060(3) 0.066(3) -0.005(2) 0.022(2) -0.024(2) C4 0.095(3) 0.078(3) 0.065(3) -0.014(3) 0.029(2) -0.032(3) C5 0.055(3) 0.027(3) 0.058(3) 0.0026(18) 0.017(2) 0.004(2) C6 0.052(2) 0.027(2) 0.061(2) -0.0032(19) 0.019(2) -0.0002(18) C7 0.055(2) 0.038(2) 0.067(3) -0.006(2) 0.021(2) -0.004(2) C8 0.061(3) 0.047(2) 0.069(3) 0.004(2) 0.018(2) 0.001(2) C9 0.090(3) 0.087(4) 0.082(3) -0.002(3) 0.042(3) 0.009(3) C10 0.070(3) 0.172(6) 0.074(3) -0.007(3) 0.009(3) 0.002(4) C11 0.054(2) 0.026(2) 0.069(3) 0.000(2) 0.021(2) 0.0004(18) C12 0.052(2) 0.032(2) 0.066(3) -0.008(2) 0.019(2) -0.0093(19) C13 0.042(2) 0.049(3) 0.061(3) -0.011(2) 0.014(2) -0.010(2) C14 0.082(3) 0.090(4) 0.061(3) -0.011(3) 0.027(2) -0.004(3) C15 0.082(3) 0.085(4) 0.081(3) 0.012(3) 0.037(2) 0.003(3) C16 0.047(2) 0.031(2) 0.051(2) -0.0001(18) 0.0076(18) 0.009(2) C17 0.069(3) 0.053(3) 0.055(2) 0.000(2) 0.012(2) 0.011(2) C18 0.067(3) 0.035(3) 0.079(3) -0.001(2) 0.011(2) 0.009(2) C19 0.058(2) 0.048(3) 0.058(2) 0.002(2) 0.013(2) 0.011(2) C20 0.056(3) 0.022(2) 0.062(2) -0.0062(19) 0.023(2) -0.002(2) C21 0.049(2) 0.027(2) 0.057(2) 0.0021(17) 0.023(2) 0.0019(17) C22 0.050(2) 0.036(2) 0.061(2) 0.0077(19) 0.022(2) 0.0098(19) C23 0.066(3) 0.039(2) 0.065(3) 0.0040(19) 0.027(2) 0.003(2) C24 0.080(3) 0.085(4) 0.072(3) 0.015(2) 0.035(2) 0.005(3) C25 0.079(3) 0.107(4) 0.068(3) 0.012(3) 0.014(2) -0.001(3) C26 0.048(2) 0.029(2) 0.064(2) -0.002(2) 0.019(2) 0.0074(19) C27 0.045(2) 0.027(2) 0.061(2) 0.0009(19) 0.0130(19) 0.0048(18) C28 0.038(2) 0.041(3) 0.058(3) -0.005(2) 0.0118(19) 0.003(2) C29 0.070(3) 0.078(3) 0.049(2) -0.002(2) 0.020(2) 0.013(2) C30 0.064(3) 0.081(3) 0.056(2) -0.007(2) 0.023(2) 0.002(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 C5 1.354(4) . ? O1 C1 1.472(4) . ? O2 C5 1.199(4) . ? O3 C13 1.218(4) . ? O4 C13 1.335(4) . ? O4 C14 1.471(5) . ? O5 C20 1.353(4) . ? O5 C16 1.478(4) . ? O6 C20 1.217(4) . ? O7 C28 1.206(4) . ? O8 C28 1.346(4) . ? O8 C29 1.458(4) . ? N1 C5 1.356(5) . ? N1 C6 1.450(4) . ? N2 C20 1.347(5) . ? N2 C21 1.456(4) . ? C1 C3 1.510(5) . ? C1 C4 1.509(5) . ? C1 C2 1.521(6) . ? C6 C11 1.495(5) . ? C6 C7 1.535(5) . ? C7 C8 1.522(5) . ? C8 C10 1.520(5) . ? C8 C9 1.521(5) . ? C11 C12 1.323(4) . ? C12 C13 1.462(5) . ? C14 C15 1.479(6) . ? C16 C19 1.505(5) . ? C16 C18 1.522(5) . ? C16 C17 1.522(4) . ? C21 C26 1.502(5) . ? C21 C22 1.535(5) . ? C22 C23 1.521(5) . ? C23 C24 1.516(5) . ? C23 C25 1.528(5) . ? C26 C27 1.324(4) . ? C27 C28 1.472(5) . ? C29 C30 1.501(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 C5 O1 C1 119.5(3) . . ? C13 O4 C14 117.1(3) . . ? C20 O5 C16 120.3(3) . . ? C28 O8 C29 115.7(3) . . ? C5 N1 C6 121.9(3) . . ? C20 N2 C21 121.4(3) . . ? O1 C1 C3 110.5(3) . . ? O1 C1 C4 110.5(3) . . ? C3 C1 C4 111.6(3) . . ? O1 C1 C2 102.4(3) . . ? C3 C1 C2 110.6(3) . . ? C4 C1 C2 110.8(3) . . ? O2 C5 N1 124.4(3) . . ? O2 C5 O1 126.3(4) . . ? N1 C5 O1 109.3(3) . . ? N1 C6 C11 112.6(3) . . ? N1 C6 C7 109.3(3) . . ? C11 C6 C7 110.9(3) . . ? C8 C7 C6 114.4(3) . . ? C7 C8 C10 110.3(3) . . ? C7 C8 C9 112.0(3) . . ? C10 C8 C9 109.8(4) . . ? C12 C11 C6 128.3(3) . . ? C11 C12 C13 121.4(4) . . ? O3 C13 O4 123.1(4) . . ? O3 C13 C12 125.1(4) . . ? O4 C13 C12 111.8(4) . . ? O4 C14 C15 109.4(3) . . ? O5 C16 C19 109.5(3) . . ? O5 C16 C18 102.5(3) . . ? C19 C16 C18 111.3(3) . . ? O5 C16 C17 110.6(3) . . ? C19 C16 C17 112.1(3) . . ? C18 C16 C17 110.4(3) . . ? O6 C20 N2 124.5(3) . . ? O6 C20 O5 125.3(4) . . ? N2 C20 O5 110.2(4) . . ? N2 C21 C26 113.3(3) . . ? N2 C21 C22 109.5(3) . . ? C26 C21 C22 110.9(3) . . ? C23 C22 C21 116.0(3) . . ? C24 C23 C22 111.7(3) . . ? C24 C23 C25 109.2(3) . . ? C22 C23 C25 110.5(3) . . ? C27 C26 C21 127.8(3) . . ? C26 C27 C28 121.3(3) . . ? O7 C28 O8 123.8(3) . . ? O7 C28 C27 125.2(4) . . ? O8 C28 C27 111.0(4) . . ? O8 C29 C30 111.3(3) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 24.28 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.110 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.027 data_mgk _database_code_depnum_ccdc_archive 'CCDC 825102' #TrackingRef 'Boc-dgIle.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(4S,5S,E)-ethyl 4-(tert-butoxycarbonylamino)-5-methylhept-2-enoate' _chemical_name_common Boc-dgI-OEt _chemical_formula_moiety 'C15 H27 N O4' _chemical_formula_sum 'C15 H27 N O4' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method EtOAc/Hexane _chemical_melting_point ? _exptl_crystal_description 'Rectangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 200(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 285.38 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration syn 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 10.153(3) _cell_length_b 10.273(3) _cell_length_c 16.191(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1688.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30707 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.60 _reflns_number_total 4302 _reflns_number_gt 3750 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0460P)^2^+0.2308P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(9) _refine_ls_number_reflns 4302 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _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 C1 C 0.27512(16) 0.49741(13) 0.22488(11) 0.0525(4) Uani 1 1 d . . . H1A H 0.2009 0.5047 0.2613 0.079 Uiso 1 1 calc R . . H1B H 0.3306 0.4273 0.2429 0.079 Uiso 1 1 calc R . . H1C H 0.2448 0.4804 0.1698 0.079 Uiso 1 1 calc R . . C2 C 0.39333(17) 0.65858(16) 0.31258(9) 0.0519(4) Uani 1 1 d . . . H2A H 0.4429 0.7381 0.3118 0.078 Uiso 1 1 calc R . . H2B H 0.4467 0.5900 0.3350 0.078 Uiso 1 1 calc R . . H2C H 0.3162 0.6698 0.3462 0.078 Uiso 1 1 calc R . . C3 C 0.46893(15) 0.61572(14) 0.16819(9) 0.0478(3) Uani 1 1 d . . . H3A H 0.4382 0.6023 0.1128 0.072 Uiso 1 1 calc R . . H3B H 0.5244 0.5443 0.1842 0.072 Uiso 1 1 calc R . . H3C H 0.5182 0.6954 0.1708 0.072 Uiso 1 1 calc R . . C4 C 0.35277(13) 0.62377(12) 0.22598(8) 0.0380(3) Uani 1 1 d . . . C5 C 0.29026(12) 0.84539(11) 0.18790(8) 0.0339(2) Uani 1 1 d . . . C6 C 0.19671(13) 1.05684(11) 0.15448(9) 0.0381(3) Uani 1 1 d . . . H6 H 0.2907 1.0777 0.1504 0.046 Uiso 1 1 calc R . . C7 C 0.13166(13) 1.10986(12) 0.07587(9) 0.0411(3) Uani 1 1 d . . . H7 H 0.1538 1.2026 0.0726 0.049 Uiso 1 1 calc R . . C8 C 0.18915(18) 1.04569(16) -0.00010(10) 0.0547(4) Uani 1 1 d . . . H8A H 0.2836 1.0485 0.0027 0.082 Uiso 1 1 calc R . . H8B H 0.1599 1.0911 -0.0486 0.082 Uiso 1 1 calc R . . H8C H 0.1605 0.9567 -0.0027 0.082 Uiso 1 1 calc R . . C9 C -0.01792(14) 1.10062(15) 0.07761(10) 0.0487(3) Uani 1 1 d . . . H9A H -0.0434 1.0098 0.0736 0.058 Uiso 1 1 calc R . . H9B H -0.0495 1.1334 0.1302 0.058 Uiso 1 1 calc R . . C10 C 0.14649(13) 1.12448(12) 0.22992(9) 0.0409(3) Uani 1 1 d . . . H10 H 0.1493 1.2150 0.2296 0.049 Uiso 1 1 calc R . . C11 C 0.09900(14) 1.06918(13) 0.29631(9) 0.0423(3) Uani 1 1 d . . . H11 H 0.0940 0.9789 0.2989 0.051 Uiso 1 1 calc R . . C12 C 0.05335(14) 1.14716(15) 0.36688(10) 0.0471(3) Uani 1 1 d . . . C26 C -0.08346(18) 1.17589(17) 0.00871(12) 0.0627(5) Uani 1 1 d . . . H26A H -0.0545 1.2648 0.0102 0.094 Uiso 1 1 calc R . . H26B H -0.1773 1.1728 0.0156 0.094 Uiso 1 1 calc R . . H26C H -0.0602 1.1379 -0.0435 0.094 Uiso 1 1 calc R . . C30 C -0.0293(2) 1.1338(2) 0.50397(12) 0.0778(6) Uani 1 1 d . . . H30A H 0.0129 1.0909 0.5503 0.093 Uiso 1 1 calc R . . H30B H -0.0009 1.2239 0.5034 0.093 Uiso 1 1 calc R . . C31 C -0.1692(2) 1.1287(3) 0.51436(13) 0.0852(7) Uani 1 1 d . . . H31A H -0.2111 1.1751 0.4701 0.128 Uiso 1 1 calc R . . H31B H -0.1927 1.1679 0.5661 0.128 Uiso 1 1 calc R . . H31C H -0.1978 1.0396 0.5138 0.128 Uiso 1 1 calc R . . N2 N 0.18751(10) 0.91597(9) 0.16081(7) 0.0368(2) Uani 1 1 d . . . H2 H 0.1156 0.8774 0.1471 0.044 Uiso 1 1 d R . . O1 O 0.25545(9) 0.71940(8) 0.19546(6) 0.0381(2) Uani 1 1 d . . . O2 O 0.39821(9) 0.88964(9) 0.20223(7) 0.0474(2) Uani 1 1 d . . . O3 O 0.05497(11) 1.26476(10) 0.36965(8) 0.0594(3) Uani 1 1 d . . . O4 O 0.01107(12) 1.07091(12) 0.42757(7) 0.0606(3) Uani 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 C1 0.0564(9) 0.0355(7) 0.0656(10) 0.0072(6) -0.0021(7) 0.0036(6) C2 0.0561(9) 0.0598(9) 0.0397(7) 0.0027(6) -0.0058(6) 0.0111(7) C3 0.0493(8) 0.0461(7) 0.0479(8) 0.0052(6) 0.0051(6) 0.0139(6) C4 0.0389(7) 0.0345(6) 0.0406(7) 0.0035(5) -0.0032(5) 0.0086(5) C5 0.0336(6) 0.0309(5) 0.0372(6) -0.0035(5) -0.0036(5) 0.0001(5) C6 0.0318(6) 0.0268(5) 0.0557(8) 0.0013(5) -0.0052(6) -0.0022(5) C7 0.0397(7) 0.0324(6) 0.0512(7) 0.0058(5) 0.0011(6) -0.0029(5) C8 0.0569(10) 0.0498(8) 0.0573(9) 0.0004(7) 0.0063(8) 0.0000(7) C9 0.0401(7) 0.0505(8) 0.0554(8) 0.0151(7) -0.0040(6) 0.0024(6) C10 0.0370(7) 0.0285(5) 0.0573(8) -0.0044(5) -0.0116(6) 0.0022(5) C11 0.0413(7) 0.0329(6) 0.0527(8) -0.0057(6) -0.0094(6) 0.0058(5) C12 0.0347(7) 0.0504(8) 0.0562(8) -0.0150(7) -0.0152(6) 0.0111(6) C26 0.0574(10) 0.0617(10) 0.0690(11) 0.0180(8) -0.0092(8) 0.0135(8) C30 0.0703(12) 0.1055(16) 0.0575(10) -0.0291(11) 0.0019(9) 0.0078(11) C31 0.0682(13) 0.128(2) 0.0596(11) -0.0118(12) 0.0084(9) -0.0061(13) N2 0.0293(5) 0.0274(5) 0.0536(6) -0.0018(4) -0.0063(5) -0.0011(4) O1 0.0355(4) 0.0289(4) 0.0498(5) 0.0010(4) -0.0083(4) 0.0025(3) O2 0.0352(5) 0.0390(5) 0.0680(7) -0.0001(4) -0.0143(5) -0.0020(4) O3 0.0512(6) 0.0472(6) 0.0800(8) -0.0241(5) -0.0161(6) 0.0124(5) O4 0.0628(7) 0.0679(7) 0.0511(6) -0.0122(6) 0.0021(6) 0.0084(6) _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 C1 C4 1.519(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.504(2) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.508(2) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 O1 1.4784(15) . ? C5 O2 1.2090(15) . ? C5 N2 1.3440(16) . ? C5 O1 1.3473(15) . ? C6 N2 1.4538(15) . ? C6 C10 1.495(2) . ? C6 C7 1.534(2) . ? C6 H6 0.9800 . ? C7 C8 1.513(2) . ? C7 C9 1.522(2) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C26 1.512(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.308(2) . ? C10 H10 0.9300 . ? C11 C12 1.470(2) . ? C11 H11 0.9300 . ? C12 O3 1.2091(18) . ? C12 O4 1.328(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C30 C31 1.431(3) . ? C30 O4 1.454(2) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? N2 H2 0.8600 . ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C2 109.66(11) . . ? O1 C4 C3 110.60(10) . . ? C2 C4 C3 112.17(13) . . ? O1 C4 C1 102.54(11) . . ? C2 C4 C1 110.86(12) . . ? C3 C4 C1 110.60(12) . . ? O2 C5 N2 124.30(11) . . ? O2 C5 O1 125.56(11) . . ? N2 C5 O1 110.14(10) . . ? N2 C6 C10 112.54(12) . . ? N2 C6 C7 112.60(11) . . ? C10 C6 C7 111.47(11) . . ? N2 C6 H6 106.6 . . ? C10 C6 H6 106.6 . . ? C7 C6 H6 106.6 . . ? C8 C7 C9 111.90(13) . . ? C8 C7 C6 110.72(12) . . ? C9 C7 C6 113.09(12) . . ? C8 C7 H7 106.9 . . ? C9 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C26 C9 C7 113.18(13) . . ? C26 C9 H9A 108.9 . . ? C7 C9 H9A 108.9 . . ? C26 C9 H9B 108.9 . . ? C7 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C6 126.53(11) . . ? C11 C10 H10 116.7 . . ? C6 C10 H10 116.7 . . ? C10 C11 C12 121.21(13) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? O3 C12 O4 124.50(15) . . ? O3 C12 C11 124.68(16) . . ? O4 C12 C11 110.82(13) . . ? C9 C26 H26A 109.5 . . ? C9 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C9 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C31 C30 O4 111.33(18) . . ? C31 C30 H30A 109.4 . . ? O4 C30 H30A 109.4 . . ? C31 C30 H30B 109.4 . . ? O4 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C5 N2 C6 120.67(11) . . ? C5 N2 H2 119.6 . . ? C6 N2 H2 119.7 . . ? C5 O1 C4 119.57(10) . . ? C12 O4 C30 117.30(15) . . ? 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 N2 C6 C7 C8 -55.61(15) . . . . ? C10 C6 C7 C8 176.81(12) . . . . ? N2 C6 C7 C9 70.88(16) . . . . ? C10 C6 C7 C9 -56.70(15) . . . . ? C8 C7 C9 C26 -65.47(17) . . . . ? C6 C7 C9 C26 168.67(13) . . . . ? N2 C6 C10 C11 0.30(19) . . . . ? C7 C6 C10 C11 127.92(14) . . . . ? C6 C10 C11 C12 179.62(12) . . . . ? C10 C11 C12 O3 0.3(2) . . . . ? C10 C11 C12 O4 -179.12(13) . . . . ? O2 C5 N2 C6 -6.2(2) . . . . ? O1 C5 N2 C6 174.60(12) . . . . ? C10 C6 N2 C5 -93.85(15) . . . . ? C7 C6 N2 C5 139.13(12) . . . . ? O2 C5 O1 C4 1.93(19) . . . . ? N2 C5 O1 C4 -178.88(10) . . . . ? C2 C4 O1 C5 62.24(15) . . . . ? C3 C4 O1 C5 -61.98(15) . . . . ? C1 C4 O1 C5 -179.93(12) . . . . ? O3 C12 O4 C30 -3.4(2) . . . . ? C11 C12 O4 C30 176.07(14) . . . . ? C31 C30 O4 C12 108.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.60 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.030 data_2c _database_code_depnum_ccdc_archive 'CCDC 907818' #TrackingRef 'web_deposit_cif_file_0_AnupamBandyopadhyay_1351168653.ANULEUNMOET.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Boc-gL(b-CH2NO2)-COOEt _chemical_name_common ? _chemical_formula_moiety 'C16 H30 N2 O6' _chemical_formula_sum 'C16 H30 N2 O6' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method EtOAc _chemical_melting_point ? _exptl_crystal_description 'thin rod' _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 346.42 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 11.306(6) _cell_length_b 31.857(16) _cell_length_c 5.353(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1928.2(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10883 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0998 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4625 _reflns_number_gt 2600 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1258P)^2^+0.0000P] 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 0.011(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 3(3) _refine_ls_number_reflns 4625 _refine_ls_number_parameters 224 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1599 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2660 _refine_ls_wR_factor_gt 0.2320 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.193 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.011 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 0.2206(4) 0.22852(9) 0.5784(5) 0.0433(10) Uani 1 1 d . . . O2 O 0.2092(3) 0.17427(9) 0.3052(5) 0.0374(8) Uani 1 1 d . . . O3 O -0.1488(4) 0.13189(11) 0.9800(7) 0.0574(11) Uani 1 1 d . . . O4 O -0.1998(4) 0.09223(12) 0.6737(8) 0.0633(12) Uani 1 1 d . . . O5 O 0.1006(3) 0.05249(9) 1.2682(6) 0.0393(9) Uani 1 1 d . . . O6 O 0.1635(4) -0.00050(9) 1.0287(6) 0.0540(12) Uani 1 1 d . . . N1 N 0.2125(4) 0.16449(10) 0.7273(6) 0.0372(10) Uani 1 1 d . . . H1 H 0.2159 0.1771 0.8693 0.045 Uiso 1 1 calc R . . N2 N -0.1290(5) 0.11553(12) 0.7796(9) 0.0490(12) Uani 1 1 d . . . C1 C 0.2231(5) 0.26122(13) 0.3831(8) 0.0400(13) Uani 1 1 d . . . C2 C 0.3342(4) 0.25696(15) 0.2261(10) 0.0406(12) Uani 1 1 d . . . H2A H 0.4021 0.2558 0.3336 0.061 Uiso 1 1 calc R . . H2B H 0.3409 0.2807 0.1167 0.061 Uiso 1 1 calc R . . H2C H 0.3298 0.2317 0.1288 0.061 Uiso 1 1 calc R . . C3 C 0.2296(8) 0.30101(15) 0.5422(11) 0.077(2) Uani 1 1 d . . . H3A H 0.1649 0.3013 0.6582 0.115 Uiso 1 1 calc R . . H3B H 0.2250 0.3252 0.4359 0.115 Uiso 1 1 calc R . . H3C H 0.3030 0.3014 0.6323 0.115 Uiso 1 1 calc R . . C4 C 0.1125(5) 0.26054(16) 0.2277(10) 0.0478(14) Uani 1 1 d . . . H4A H 0.1077 0.2344 0.1391 0.072 Uiso 1 1 calc R . . H4B H 0.1144 0.2833 0.1103 0.072 Uiso 1 1 calc R . . H4C H 0.0448 0.2635 0.3344 0.072 Uiso 1 1 calc R . . C5 C 0.2127(5) 0.18803(12) 0.5178(8) 0.0325(11) Uani 1 1 d . . . C6 C 0.2067(5) 0.11887(12) 0.7250(8) 0.0384(12) Uani 1 1 d . . . H6 H 0.2151 0.1095 0.5515 0.046 Uiso 1 1 calc R . . C7 C 0.3093(6) 0.10069(17) 0.8736(10) 0.0588(18) Uani 1 1 d . . . H7A H 0.3091 0.0704 0.8531 0.071 Uiso 1 1 calc R . . H7B H 0.2963 0.1066 1.0492 0.071 Uiso 1 1 calc R . . C8 C 0.4367(8) 0.1181(4) 0.7971(15) 0.156(6) Uani 1 1 d D . . H8 H 0.4587 0.1450 0.8729 0.188 Uiso 1 1 calc R . . C9 C 0.4751(11) 0.1123(4) 0.546(2) 0.163(6) Uani 1 1 d D . . H9A H 0.5595 0.1091 0.5427 0.245 Uiso 1 1 calc R . . H9B H 0.4530 0.1363 0.4480 0.245 Uiso 1 1 calc R . . H9C H 0.4386 0.0876 0.4779 0.245 Uiso 1 1 calc R . . C10 C 0.5096(13) 0.0780(5) 0.896(3) 0.206(6) Uani 1 1 d U . . H10A H 0.5417 0.0629 0.7566 0.309 Uiso 1 1 calc R . . H10B H 0.4577 0.0599 0.9889 0.309 Uiso 1 1 calc R . . H10C H 0.5729 0.0873 1.0025 0.309 Uiso 1 1 calc R . . C11 C 0.0855(5) 0.10437(13) 0.8191(8) 0.0401(13) Uani 1 1 d . . . H11 H 0.0756 0.1149 0.9897 0.048 Uiso 1 1 calc R . . C12 C -0.0118(5) 0.12284(15) 0.6610(9) 0.0401(12) Uani 1 1 d . . . H12A H 0.0011 0.1528 0.6411 0.048 Uiso 1 1 calc R . . H12B H -0.0106 0.1101 0.4966 0.048 Uiso 1 1 calc R . . C13 C 0.0735(6) 0.05646(13) 0.8272(8) 0.0500(15) Uani 1 1 d . . . H13A H -0.0090 0.0491 0.8021 0.060 Uiso 1 1 calc R . . H13B H 0.1183 0.0446 0.6898 0.060 Uiso 1 1 calc R . . C14 C 0.1152(5) 0.03694(13) 1.0661(8) 0.0385(13) Uani 1 1 d . . . C15 C 0.1986(5) -0.02382(13) 1.2530(9) 0.0453(14) Uani 1 1 d . . . H15A H 0.2049 -0.0535 1.2141 0.054 Uiso 1 1 calc R . . H15B H 0.1389 -0.0204 1.3817 0.054 Uiso 1 1 calc R . . C16 C 0.3151(6) -0.00787(16) 1.3464(12) 0.0611(18) Uani 1 1 d . . . H16A H 0.3737 -0.0109 1.2179 0.092 Uiso 1 1 calc R . . H16B H 0.3386 -0.0237 1.4907 0.092 Uiso 1 1 calc R . . H16C H 0.3078 0.0212 1.3905 0.092 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 0.093(3) 0.0190(15) 0.0181(14) 0.0007(11) 0.0050(18) -0.0083(17) O2 0.070(2) 0.0247(15) 0.0176(14) -0.0008(11) 0.0082(17) -0.0014(15) O3 0.086(3) 0.043(2) 0.043(2) -0.0129(17) 0.029(2) -0.001(2) O4 0.081(3) 0.043(2) 0.065(3) -0.0228(19) 0.015(3) -0.015(2) O5 0.074(2) 0.0290(16) 0.0147(14) -0.0017(12) -0.0001(16) -0.0016(15) O6 0.122(4) 0.0163(14) 0.0235(16) 0.0027(12) -0.003(2) 0.0074(18) N1 0.072(3) 0.0231(18) 0.0164(16) -0.0002(13) 0.001(2) 0.0064(18) N2 0.080(3) 0.024(2) 0.044(3) -0.0012(19) 0.016(3) 0.001(2) C1 0.072(4) 0.022(2) 0.026(2) 0.0030(16) 0.003(3) -0.005(2) C2 0.044(3) 0.043(3) 0.035(3) 0.007(2) -0.002(3) -0.006(2) C3 0.171(8) 0.021(2) 0.039(3) -0.002(2) 0.022(4) -0.008(3) C4 0.058(4) 0.045(3) 0.040(3) 0.009(2) 0.018(3) 0.015(2) C5 0.056(3) 0.0181(19) 0.024(2) -0.0011(16) -0.003(2) 0.002(2) C6 0.070(3) 0.022(2) 0.024(2) -0.0003(16) 0.012(3) 0.010(2) C7 0.083(5) 0.055(3) 0.038(3) 0.022(2) 0.025(3) 0.038(3) C8 0.081(6) 0.332(16) 0.056(5) 0.078(7) 0.032(5) 0.132(8) C9 0.132(10) 0.200(12) 0.158(11) 0.080(10) 0.065(9) 0.044(8) C10 0.162(9) 0.252(10) 0.203(10) 0.088(8) 0.028(8) 0.069(8) C11 0.085(4) 0.016(2) 0.020(2) 0.0053(16) 0.015(3) 0.005(2) C12 0.062(4) 0.032(3) 0.027(2) 0.0064(19) 0.010(3) 0.003(2) C13 0.119(5) 0.018(2) 0.0125(19) -0.0005(16) -0.003(3) 0.003(3) C14 0.082(4) 0.020(2) 0.0138(19) 0.0044(16) -0.001(2) -0.003(2) C15 0.088(4) 0.022(2) 0.026(2) 0.0071(17) -0.010(3) 0.001(2) C16 0.077(5) 0.037(3) 0.069(4) 0.005(3) 0.001(4) 0.011(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 C5 1.333(5) . ? O1 C1 1.476(5) . ? O2 C5 1.220(5) . ? O3 N2 1.213(5) . ? O4 N2 1.230(6) . ? O5 C14 1.201(5) . ? O6 C14 1.327(6) . ? O6 C15 1.467(5) . ? N1 C5 1.349(5) . ? N1 C6 1.455(5) . ? N2 C12 1.488(7) . ? C1 C4 1.502(8) . ? C1 C2 1.516(7) . ? C1 C3 1.529(6) . ? C6 C7 1.521(7) . ? C6 C11 1.531(7) . ? C7 C8 1.597(13) . ? C8 C9 1.425(12) . ? C8 C10 1.610(14) . ? C11 C12 1.508(7) . ? C11 C13 1.533(6) . ? C13 C14 1.498(6) . ? C15 C16 1.498(8) . ? 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 C5 O1 C1 120.8(3) . . ? C14 O6 C15 116.3(3) . . ? C5 N1 C6 123.3(4) . . ? O3 N2 O4 123.2(5) . . ? O3 N2 C12 118.3(5) . . ? O4 N2 C12 118.5(4) . . ? O1 C1 C4 111.4(4) . . ? O1 C1 C2 110.2(4) . . ? C4 C1 C2 112.4(4) . . ? O1 C1 C3 101.0(4) . . ? C4 C1 C3 111.1(5) . . ? C2 C1 C3 110.1(5) . . ? O2 C5 O1 125.2(4) . . ? O2 C5 N1 125.1(4) . . ? O1 C5 N1 109.6(3) . . ? N1 C6 C7 110.0(5) . . ? N1 C6 C11 109.8(4) . . ? C7 C6 C11 113.3(4) . . ? C6 C7 C8 114.9(4) . . ? C9 C8 C7 118.1(11) . . ? C9 C8 C10 93.0(9) . . ? C7 C8 C10 95.8(9) . . ? C12 C11 C6 110.6(4) . . ? C12 C11 C13 109.8(4) . . ? C6 C11 C13 112.9(4) . . ? N2 C12 C11 110.5(4) . . ? C14 C13 C11 114.2(4) . . ? O5 C14 O6 124.3(4) . . ? O5 C14 C13 123.7(4) . . ? O6 C14 C13 112.0(4) . . ? O6 C15 C16 109.9(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.974 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.086 data_2bacid _database_code_depnum_ccdc_archive 'CCDC 907819' #TrackingRef 'web_deposit_cif_file_1_AnupamBandyopadhyay_1351168653.ANUGILMA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Boc-gI(b-CH2NO2)-COOH _chemical_name_common ? _chemical_formula_moiety 'C14 H26 N2 O6' _chemical_formula_sum 'C14 H26 N2 O6' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method EtOAC/Hexane _chemical_melting_point ? _exptl_crystal_description 'rod shapped' _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 318.37 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.226(8) _cell_length_b 7.133(5) _cell_length_c 12.018(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.948(15) _cell_angle_gamma 90.00 _cell_volume 898.7(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9043 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4252 _reflns_number_gt 3359 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0561P)^2^+0.0050P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(10) _refine_ls_number_reflns 4252 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _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 0.32378(11) 0.45800(17) 0.70791(11) 0.0273(3) Uani 1 1 d . . . O2 O 0.38667(12) 0.15511(18) 0.75401(12) 0.0311(3) Uani 1 1 d . . . O3 O 0.41538(11) 0.84868(19) 0.88026(13) 0.0342(3) Uani 1 1 d . . . H3 H 0.3988 0.9446 0.8400 0.051 Uiso 1 1 calc R . . O4 O 0.23009(14) 0.9117(2) 0.90064(16) 0.0504(4) Uani 1 1 d . . . O5 O 0.1687(2) 0.5310(4) 1.18928(17) 0.0953(8) Uani 1 1 d . . . O6 O 0.36005(16) 0.4371(3) 1.24709(14) 0.0625(5) Uani 1 1 d . . . N1 N 0.24523(13) 0.2915(2) 0.82303(13) 0.0261(3) Uani 1 1 d . . . H1 H 0.2446 0.1896 0.8611 0.031 Uiso 1 1 calc R . . N2 N 0.25456(17) 0.4504(2) 1.17286(15) 0.0380(4) Uani 1 1 d . . . C1 C 0.39257(17) 0.4801(3) 0.62356(17) 0.0307(4) Uani 1 1 d . . . C2 C 0.36189(19) 0.6826(3) 0.5831(2) 0.0410(5) Uani 1 1 d . . . H2A H 0.2711 0.6993 0.5506 0.061 Uiso 1 1 calc R . . H2B H 0.3973 0.7112 0.5233 0.061 Uiso 1 1 calc R . . H2C H 0.3979 0.7650 0.6500 0.061 Uiso 1 1 calc R . . C3 C 0.3380(2) 0.3444(4) 0.52135(19) 0.0500(6) Uani 1 1 d . . . H3A H 0.3593 0.2185 0.5497 0.075 Uiso 1 1 calc R . . H3B H 0.3732 0.3706 0.4610 0.075 Uiso 1 1 calc R . . H3C H 0.2470 0.3580 0.4884 0.075 Uiso 1 1 calc R . . C4 C 0.53448(17) 0.4547(4) 0.6885(2) 0.0433(5) Uani 1 1 d . . . H4A H 0.5616 0.5289 0.7598 0.065 Uiso 1 1 calc R . . H4B H 0.5794 0.4943 0.6379 0.065 Uiso 1 1 calc R . . H4C H 0.5525 0.3250 0.7088 0.065 Uiso 1 1 calc R . . C5 C 0.32260(16) 0.2937(2) 0.75996(15) 0.0237(4) Uani 1 1 d . . . C6 C 0.16153(14) 0.4420(2) 0.83484(15) 0.0241(3) Uani 1 1 d . . . H6 H 0.1630 0.5423 0.7796 0.029 Uiso 1 1 calc R . . C7 C 0.02399(16) 0.3658(3) 0.79468(18) 0.0329(4) Uani 1 1 d . . . H7 H 0.0261 0.2532 0.8421 0.039 Uiso 1 1 calc R . . C8 C -0.0343(2) 0.4607(5) 0.5745(2) 0.0649(8) Uani 1 1 d . . . H8A H -0.0876 0.5591 0.5850 0.097 Uiso 1 1 calc R . . H8B H -0.0709 0.4113 0.4952 0.097 Uiso 1 1 calc R . . H8C H 0.0491 0.5098 0.5867 0.097 Uiso 1 1 calc R . . C9 C -0.02381(19) 0.3056(3) 0.66406(19) 0.0438(5) Uani 1 1 d . . . H9A H 0.0332 0.2100 0.6545 0.053 Uiso 1 1 calc R . . H9B H -0.1072 0.2485 0.6450 0.053 Uiso 1 1 calc R . . C10 C -0.06646(19) 0.5050(4) 0.8207(3) 0.0564(7) Uani 1 1 d . . . H10A H -0.0549 0.6271 0.7925 0.085 Uiso 1 1 calc R . . H10B H -0.0482 0.5101 0.9050 0.085 Uiso 1 1 calc R . . H10C H -0.1530 0.4651 0.7808 0.085 Uiso 1 1 calc R . . C11 C 0.21331(16) 0.5236(2) 0.96157(16) 0.0241(4) Uani 1 1 d . . . H11 H 0.1509 0.6139 0.9694 0.029 Uiso 1 1 calc R . . C12 C 0.2297(2) 0.3674(3) 1.05353(17) 0.0330(4) Uani 1 1 d . . . H12A H 0.1530 0.2915 1.0308 0.040 Uiso 1 1 calc R . . H12B H 0.3003 0.2871 1.0560 0.040 Uiso 1 1 calc R . . C13 C 0.33929(16) 0.6268(3) 0.98431(17) 0.0270(4) Uani 1 1 d . . . H13A H 0.3794 0.6514 1.0690 0.032 Uiso 1 1 calc R . . H13B H 0.3960 0.5470 0.9606 0.032 Uiso 1 1 calc R . . C14 C 0.32115(16) 0.8101(2) 0.91704(16) 0.0264(4) Uani 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 O1 0.0305(6) 0.0238(6) 0.0333(7) 0.0070(6) 0.0181(5) 0.0013(5) O2 0.0380(7) 0.0222(6) 0.0411(8) 0.0042(6) 0.0238(6) 0.0044(6) O3 0.0286(6) 0.0273(7) 0.0504(9) 0.0097(6) 0.0185(6) -0.0002(5) O4 0.0466(8) 0.0263(8) 0.0931(13) 0.0216(8) 0.0431(8) 0.0104(6) O5 0.0943(14) 0.139(2) 0.0601(12) -0.0044(13) 0.0369(11) 0.0690(15) O6 0.0593(10) 0.0909(15) 0.0345(9) 0.0038(10) 0.0132(8) 0.0062(11) N1 0.0348(8) 0.0160(7) 0.0341(9) 0.0048(6) 0.0204(7) 0.0019(6) N2 0.0535(10) 0.0317(9) 0.0380(10) 0.0056(8) 0.0275(9) 0.0092(8) C1 0.0304(8) 0.0356(11) 0.0314(10) 0.0075(8) 0.0175(8) -0.0011(8) C2 0.0403(11) 0.0420(12) 0.0456(13) 0.0198(10) 0.0215(10) 0.0030(10) C3 0.0641(14) 0.0572(15) 0.0355(13) -0.0016(11) 0.0263(11) -0.0083(12) C4 0.0286(9) 0.0477(13) 0.0568(14) 0.0182(12) 0.0191(9) 0.0017(10) C5 0.0268(8) 0.0215(8) 0.0243(9) 0.0006(7) 0.0109(7) -0.0025(7) C6 0.0248(8) 0.0172(8) 0.0330(9) 0.0025(7) 0.0136(7) 0.0006(7) C7 0.0284(9) 0.0293(10) 0.0415(12) -0.0013(9) 0.0131(8) -0.0067(8) C8 0.0520(13) 0.075(2) 0.0525(16) 0.0151(15) 0.0006(11) -0.0160(15) C9 0.0373(11) 0.0468(13) 0.0414(13) 0.0007(10) 0.0070(9) -0.0135(10) C10 0.0265(10) 0.0593(16) 0.0834(18) -0.0088(14) 0.0199(11) -0.0001(11) C11 0.0266(8) 0.0166(8) 0.0325(10) 0.0011(7) 0.0149(7) 0.0004(7) C12 0.0474(11) 0.0235(9) 0.0341(11) -0.0001(8) 0.0217(9) -0.0020(9) C13 0.0281(8) 0.0210(8) 0.0310(10) 0.0042(7) 0.0094(7) 0.0007(7) C14 0.0267(8) 0.0186(8) 0.0334(10) -0.0005(7) 0.0103(7) -0.0034(7) _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 C5 1.331(2) . ? O1 C1 1.486(2) . ? O2 C5 1.240(2) . ? O3 C14 1.313(2) . ? O4 C14 1.210(2) . ? O5 N2 1.198(2) . ? O6 N2 1.205(2) . ? N1 C5 1.342(2) . ? N1 C6 1.467(2) . ? N2 C12 1.483(3) . ? C1 C4 1.513(3) . ? C1 C3 1.511(3) . ? C1 C2 1.524(3) . ? C6 C11 1.537(3) . ? C6 C7 1.543(2) . ? C7 C10 1.530(3) . ? C7 C9 1.528(3) . ? C8 C9 1.519(4) . ? C11 C13 1.530(2) . ? C11 C12 1.533(3) . ? C13 C14 1.512(3) . ? 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 C5 O1 C1 120.61(13) . . ? C5 N1 C6 127.78(14) . . ? O5 N2 O6 123.5(2) . . ? O5 N2 C12 117.81(19) . . ? O6 N2 C12 118.70(17) . . ? O1 C1 C4 110.11(15) . . ? O1 C1 C3 109.16(16) . . ? C4 C1 C3 112.85(19) . . ? O1 C1 C2 101.83(14) . . ? C4 C1 C2 110.73(17) . . ? C3 C1 C2 111.60(18) . . ? O2 C5 O1 124.86(15) . . ? O2 C5 N1 121.97(16) . . ? O1 C5 N1 113.16(14) . . ? N1 C6 C11 110.16(14) . . ? N1 C6 C7 108.42(15) . . ? C11 C6 C7 115.15(13) . . ? C10 C7 C9 112.15(18) . . ? C10 C7 C6 111.76(17) . . ? C9 C7 C6 111.42(15) . . ? C8 C9 C7 115.7(2) . . ? C13 C11 C12 110.85(15) . . ? C13 C11 C6 110.93(14) . . ? C12 C11 C6 110.14(15) . . ? N2 C12 C11 109.87(16) . . ? C14 C13 C11 112.41(14) . . ? O4 C14 O3 123.71(17) . . ? O4 C14 C13 123.31(16) . . ? O3 C14 C13 112.98(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.173 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.041 data_P3 _database_code_depnum_ccdc_archive 'CCDC 907820' #TrackingRef 'web_deposit_cif_file_2_AnupamBandyopadhyay_1351168653.DipepMA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Boc-gV(b-CH2NO2)-gL(b-CH2NO2)-COOEt _chemical_name_common ? _chemical_formula_moiety 'C24 H44 N4 O9' _chemical_formula_sum 'C24 H44 N4 O9' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method EtOAc _chemical_melting_point ? _exptl_crystal_description 'rod shapped' _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 532.63 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32' _symmetry_int_tables_number 145 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 13.503(9) _cell_length_b 13.503(9) _cell_length_c 14.005(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2211(3) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite Monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14290 _diffrn_reflns_av_R_equivalents 0.1857 _diffrn_reflns_av_sigmaI/netI 0.2766 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 29.54 _reflns_number_total 5572 _reflns_number_gt 1917 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1379P)^2^+0.6181P] 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 0.014(3) _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 -2(3) _refine_ls_number_reflns 5572 _refine_ls_number_parameters 343 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.2453 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2952 _refine_ls_wR_factor_gt 0.2072 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.878 _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 0.6184(4) 0.7967(5) 0.7211(5) 0.0483(16) Uani 1 1 d . . . O2 O 0.6970(4) 0.9190(5) 0.5952(5) 0.0481(16) Uani 1 1 d . . . O3 O 0.1676(5) 0.5125(6) 0.4650(6) 0.075(2) Uani 1 1 d . . . O4 O 0.2560(5) 0.6146(5) 0.3428(5) 0.0461(16) Uani 1 1 d . . . O5 O 0.5056(4) 0.9368(4) 0.3103(5) 0.0400(14) Uani 1 1 d . . . O6 O 1.0683(5) 1.1188(6) 0.3688(6) 0.068(2) Uani 1 1 d . . . O7 O 0.9717(6) 0.9675(6) 0.2818(7) 0.076(2) Uani 1 1 d . . . O8 O 0.6434(5) 0.9702(5) 0.0949(6) 0.0611(19) Uani 1 1 d . . . O9 O 0.7950(5) 1.1367(5) 0.1361(5) 0.0543(18) Uani 1 1 d . . . N1 N 0.5767(5) 0.7265(5) 0.5754(6) 0.048(2) Uani 1 1 d . . . H1 H 0.5368 0.6629 0.6052 0.058 Uiso 1 1 calc R . . N2 N 0.2551(6) 0.5788(6) 0.4212(6) 0.0434(19) Uani 1 1 d . . . N3 N 0.6452(5) 0.9944(5) 0.4214(6) 0.0450(19) Uani 1 1 d . . . H3 H 0.6642 0.9797 0.4760 0.054 Uiso 1 1 calc R . . N4 N 0.9792(7) 1.0366(8) 0.3438(9) 0.073(3) Uani 1 1 d . . . C1 C 0.6770(6) 0.8828(7) 0.7951(7) 0.045(2) Uani 1 1 d . . . C2 C 0.6309(9) 0.8163(10) 0.8885(9) 0.091(4) Uani 1 1 d . . . H2A H 0.5509 0.7910 0.8940 0.136 Uiso 1 1 calc R . . H2B H 0.6712 0.8649 0.9415 0.136 Uiso 1 1 calc R . . H2C H 0.6416 0.7512 0.8884 0.136 Uiso 1 1 calc R . . C3 C 0.6503(9) 0.9790(9) 0.7879(10) 0.078(3) Uani 1 1 d . . . H3A H 0.6935 1.0292 0.7365 0.117 Uiso 1 1 calc R . . H3B H 0.6702 1.0211 0.8467 0.117 Uiso 1 1 calc R . . H3C H 0.5701 0.9477 0.7758 0.117 Uiso 1 1 calc R . . C4 C 0.8057(7) 0.9301(8) 0.7884(7) 0.058(3) Uani 1 1 d . . . H4A H 0.8211 0.8679 0.7882 0.087 Uiso 1 1 calc R . . H4B H 0.8429 0.9787 0.8422 0.087 Uiso 1 1 calc R . . H4C H 0.8342 0.9733 0.7305 0.087 Uiso 1 1 calc R . . C5 C 0.6359(6) 0.8233(8) 0.6287(8) 0.044(2) Uani 1 1 d . . . C6 C 0.5763(6) 0.7234(7) 0.4724(6) 0.0336(18) Uani 1 1 d . . . H6 H 0.6404 0.7964 0.4507 0.040 Uiso 1 1 calc R . . C7 C 0.6011(7) 0.6287(7) 0.4395(7) 0.046(2) Uani 1 1 d . . . H7 H 0.5515 0.5591 0.4757 0.055 Uiso 1 1 calc R . . C8 C 0.7253(7) 0.6651(8) 0.4626(10) 0.069(3) Uani 1 1 d . . . H8A H 0.7393 0.6039 0.4474 0.104 Uiso 1 1 calc R . . H8B H 0.7392 0.6830 0.5293 0.104 Uiso 1 1 calc R . . H8C H 0.7753 0.7314 0.4256 0.104 Uiso 1 1 calc R . . C9 C 0.5785(9) 0.6008(8) 0.3322(8) 0.061(3) Uani 1 1 d . . . H9A H 0.6154 0.6704 0.2960 0.092 Uiso 1 1 calc R . . H9B H 0.4976 0.5621 0.3204 0.092 Uiso 1 1 calc R . . H9C H 0.6083 0.5524 0.3135 0.092 Uiso 1 1 calc R . . C10 C 0.4673(6) 0.7164(6) 0.4337(6) 0.0327(19) Uani 1 1 d . . . H10 H 0.4687 0.7076 0.3644 0.039 Uiso 1 1 calc R . . C11 C 0.3642(6) 0.6113(6) 0.4693(7) 0.037(2) Uani 1 1 d . . . H11A H 0.3785 0.5479 0.4639 0.044 Uiso 1 1 calc R . . H11B H 0.3554 0.6218 0.5367 0.044 Uiso 1 1 calc R . . C12 C 0.4608(6) 0.8252(6) 0.4504(6) 0.0336(19) Uani 1 1 d . . . H12A H 0.3830 0.8079 0.4388 0.040 Uiso 1 1 calc R . . H12B H 0.4780 0.8470 0.5170 0.040 Uiso 1 1 calc R . . C13 C 0.5386(7) 0.9243(6) 0.3905(7) 0.036(2) Uani 1 1 d . . . C14 C 0.7308(7) 1.0931(6) 0.3699(6) 0.041(2) Uani 1 1 d . . . H14 H 0.6893 1.1090 0.3204 0.049 Uiso 1 1 calc R . . C15 C 0.7857(9) 1.1972(7) 0.4317(8) 0.063(3) Uani 1 1 d D . . H15A H 0.8677 1.2270 0.4332 0.075 Uiso 1 1 calc R . . H15B H 0.7570 1.1763 0.4964 0.075 Uiso 1 1 calc R . . C16 C 0.7606(19) 1.2974(15) 0.3932(16) 0.198(9) Uani 1 1 d DU . . H16 H 0.6897 1.2746 0.3578 0.238 Uiso 1 1 calc R . . C17 C 0.875(3) 1.350(3) 0.337(2) 0.341(17) Uani 1 1 d DU . . H17A H 0.9003 1.4282 0.3220 0.511 Uiso 1 1 calc R . . H17B H 0.8639 1.3077 0.2786 0.511 Uiso 1 1 calc R . . H17C H 0.9321 1.3456 0.3750 0.511 Uiso 1 1 calc R . . C18 C 0.785(2) 1.370(2) 0.4845(16) 0.224(11) Uani 1 1 d DU . . H18A H 0.7479 1.3203 0.5380 0.335 Uiso 1 1 calc R . . H18B H 0.7551 1.4211 0.4769 0.335 Uiso 1 1 calc R . . H18C H 0.8655 1.4132 0.4955 0.335 Uiso 1 1 calc R . . C19 C 0.8122(7) 1.0624(7) 0.3160(7) 0.046(2) Uani 1 1 d . . . H19 H 0.8724 1.1338 0.2879 0.055 Uiso 1 1 calc R . . C20 C 0.8732(7) 1.0216(8) 0.3884(9) 0.062(3) Uani 1 1 d . . . H20A H 0.8915 1.0662 0.4466 0.074 Uiso 1 1 calc R . . H20B H 0.8229 0.9418 0.4044 0.074 Uiso 1 1 calc R . . C21 C 0.7556(7) 0.9793(7) 0.2334(7) 0.044(2) Uani 1 1 d . . . H21A H 0.8081 0.9554 0.2103 0.053 Uiso 1 1 calc R . . H21B H 0.6884 0.9118 0.2575 0.053 Uiso 1 1 calc R . . C22 C 0.7208(8) 1.0247(7) 0.1517(8) 0.049(2) Uani 1 1 d . . . C23 C 0.7783(8) 1.1903(8) 0.0569(8) 0.060(3) Uani 1 1 d . . . H23A H 0.7062 1.1892 0.0636 0.072 Uiso 1 1 calc R . . H23B H 0.7746 1.1487 -0.0007 0.072 Uiso 1 1 calc R . . C24 C 0.8719(9) 1.3090(8) 0.0487(9) 0.076(3) Uani 1 1 d . . . H24A H 0.8725 1.3513 0.1040 0.114 Uiso 1 1 calc R . . H24B H 0.8609 1.3431 -0.0075 0.114 Uiso 1 1 calc R . . H24C H 0.9434 1.3101 0.0442 0.114 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 0.042(3) 0.053(3) 0.037(4) -0.004(3) -0.002(3) 0.013(3) O2 0.040(3) 0.047(3) 0.045(5) 0.017(3) 0.001(3) 0.013(3) O3 0.039(3) 0.091(5) 0.088(7) 0.026(5) 0.019(4) 0.026(3) O4 0.051(3) 0.051(3) 0.036(5) -0.002(3) -0.012(3) 0.025(3) O5 0.042(3) 0.043(3) 0.040(4) -0.005(3) -0.002(3) 0.025(3) O6 0.046(4) 0.071(4) 0.071(6) 0.012(4) -0.007(4) 0.016(3) O7 0.071(5) 0.071(5) 0.099(8) 0.005(5) -0.011(5) 0.045(4) O8 0.045(3) 0.058(4) 0.063(6) -0.004(4) -0.003(3) 0.012(3) O9 0.052(3) 0.044(3) 0.054(5) 0.011(3) 0.004(3) 0.015(3) N1 0.032(3) 0.033(3) 0.071(7) -0.006(4) -0.009(4) 0.010(3) N2 0.045(4) 0.042(4) 0.045(6) 0.006(4) 0.009(4) 0.022(3) N3 0.048(4) 0.040(4) 0.044(6) 0.009(3) 0.002(4) 0.020(3) N4 0.054(5) 0.053(5) 0.117(11) 0.013(6) -0.012(6) 0.030(5) C1 0.033(4) 0.046(5) 0.030(6) -0.011(4) -0.003(4) 0.001(4) C2 0.063(7) 0.103(9) 0.037(8) -0.007(7) 0.007(6) -0.010(6) C3 0.071(7) 0.077(7) 0.076(10) -0.007(7) 0.008(7) 0.030(6) C4 0.047(5) 0.084(6) 0.016(6) 0.002(5) -0.017(4) 0.012(5) C5 0.028(4) 0.057(6) 0.047(7) 0.010(5) 0.006(4) 0.021(4) C6 0.039(4) 0.050(4) 0.012(5) -0.010(4) -0.009(4) 0.022(4) C7 0.049(5) 0.062(5) 0.042(7) 0.003(5) 0.000(5) 0.039(4) C8 0.054(5) 0.071(6) 0.100(11) 0.001(6) 0.005(6) 0.044(5) C9 0.089(7) 0.074(6) 0.048(8) -0.004(5) 0.005(6) 0.061(6) C10 0.037(4) 0.030(4) 0.033(6) -0.008(4) -0.004(4) 0.018(3) C11 0.042(4) 0.038(4) 0.033(6) -0.004(4) -0.005(4) 0.023(4) C12 0.034(4) 0.042(4) 0.027(5) -0.005(4) -0.001(4) 0.020(3) C13 0.045(5) 0.043(4) 0.037(6) -0.006(4) -0.007(4) 0.034(4) C14 0.048(5) 0.042(4) 0.029(6) 0.016(4) 0.011(4) 0.020(4) C15 0.080(7) 0.037(5) 0.051(8) 0.007(5) 0.018(6) 0.014(5) C16 0.208(12) 0.178(11) 0.196(13) -0.073(9) 0.005(9) 0.087(9) C17 0.341(17) 0.341(17) 0.341(17) 0.0000(10) -0.0001(10) 0.171(8) C18 0.224(11) 0.224(11) 0.224(11) -0.0003(10) -0.0001(10) 0.112(5) C19 0.041(4) 0.047(5) 0.036(6) 0.014(4) 0.001(4) 0.012(4) C20 0.044(5) 0.064(6) 0.069(9) 0.024(5) 0.016(5) 0.020(4) C21 0.040(4) 0.046(4) 0.045(7) 0.010(5) 0.018(4) 0.021(4) C22 0.044(5) 0.046(5) 0.051(8) 0.000(5) 0.016(5) 0.019(4) C23 0.061(6) 0.058(6) 0.042(7) 0.016(5) 0.008(5) 0.016(5) C24 0.078(7) 0.055(6) 0.061(9) 0.024(6) -0.007(6) 0.008(5) _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 C5 1.331(11) . ? O1 C1 1.461(10) . ? O2 C5 1.227(10) . ? O3 N2 1.232(9) . ? O4 N2 1.197(9) . ? O5 C13 1.251(10) . ? O6 N4 1.212(10) . ? O7 N4 1.241(12) . ? O8 C22 1.225(11) . ? O9 C22 1.351(10) . ? O9 C23 1.403(11) . ? N1 C5 1.364(12) . ? N1 C6 1.443(11) . ? N1 H1 0.8600 . ? N2 C11 1.473(10) . ? N3 C13 1.339(10) . ? N3 C14 1.447(10) . ? N3 H3 0.8600 . ? N4 C20 1.480(13) . ? C1 C3 1.516(13) . ? C1 C4 1.525(12) . ? C1 C2 1.531(15) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C10 1.526(10) . ? C6 C7 1.545(11) . ? C6 H6 0.9800 . ? C7 C8 1.527(12) . ? C7 C9 1.541(14) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.491(10) . ? C10 C12 1.533(9) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.480(12) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.494(13) . ? C14 C19 1.551(12) . ? C14 H14 0.9800 . ? C15 C16 1.642(17) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C18 1.544(17) . ? C16 C17 1.557(18) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C21 1.526(13) . ? C19 C20 1.569(13) . ? C19 H19 0.9800 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.480(14) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C23 C24 1.467(12) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 C5 O1 C1 121.5(7) . . ? C22 O9 C23 119.0(8) . . ? C5 N1 C6 124.6(7) . . ? C5 N1 H1 117.7 . . ? C6 N1 H1 117.7 . . ? O4 N2 O3 124.2(8) . . ? O4 N2 C11 119.5(7) . . ? O3 N2 C11 116.2(8) . . ? C13 N3 C14 124.9(8) . . ? C13 N3 H3 117.6 . . ? C14 N3 H3 117.6 . . ? O6 N4 O7 124.2(9) . . ? O6 N4 C20 116.9(11) . . ? O7 N4 C20 118.8(9) . . ? O1 C1 C3 111.6(8) . . ? O1 C1 C4 109.9(7) . . ? C3 C1 C4 110.3(7) . . ? O1 C1 C2 103.9(7) . . ? C3 C1 C2 111.0(9) . . ? C4 C1 C2 110.1(9) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 O1 126.2(9) . . ? O2 C5 N1 124.3(10) . . ? O1 C5 N1 109.5(8) . . ? N1 C6 C10 110.2(6) . . ? N1 C6 C7 108.9(7) . . ? C10 C6 C7 116.4(6) . . ? N1 C6 H6 107.0 . . ? C10 C6 H6 107.0 . . ? C7 C6 H6 107.0 . . ? C8 C7 C9 109.7(8) . . ? C8 C7 C6 109.1(7) . . ? C9 C7 C6 113.3(7) . . ? C8 C7 H7 108.2 . . ? C9 C7 H7 108.2 . . ? C6 C7 H7 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C6 110.6(6) . . ? C11 C10 C12 112.8(6) . . ? C6 C10 C12 113.7(6) . . ? C11 C10 H10 106.4 . . ? C6 C10 H10 106.4 . . ? C12 C10 H10 106.4 . . ? N2 C11 C10 116.7(7) . . ? N2 C11 H11A 108.1 . . ? C10 C11 H11A 108.1 . . ? N2 C11 H11B 108.1 . . ? C10 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C13 C12 C10 115.1(7) . . ? C13 C12 H12A 108.5 . . ? C10 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C10 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? O5 C13 N3 121.6(8) . . ? O5 C13 C12 119.4(7) . . ? N3 C13 C12 118.8(8) . . ? N3 C14 C15 111.7(8) . . ? N3 C14 C19 110.1(6) . . ? C15 C14 C19 116.7(7) . . ? N3 C14 H14 105.9 . . ? C15 C14 H14 105.9 . . ? C19 C14 H14 105.9 . . ? C14 C15 C16 112.0(11) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C18 C16 C17 106.6(15) . . ? C18 C16 C15 100.7(17) . . ? C17 C16 C15 88.4(18) . . ? C18 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C19 C14 113.8(7) . . ? C21 C19 C20 112.9(8) . . ? C14 C19 C20 110.2(8) . . ? C21 C19 H19 106.4 . . ? C14 C19 H19 106.4 . . ? C20 C19 H19 106.4 . . ? N4 C20 C19 108.7(8) . . ? N4 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? N4 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C22 C21 C19 115.3(7) . . ? C22 C21 H21A 108.4 . . ? C19 C21 H21A 108.4 . . ? C22 C21 H21B 108.4 . . ? C19 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? O8 C22 O9 119.9(9) . . ? O8 C22 C21 127.3(8) . . ? O9 C22 C21 112.2(8) . . ? O9 C23 C24 110.6(9) . . ? O9 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? O9 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 29.54 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.879 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.115