# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_C12H12N2O6 _publ_contact_author ; Prof. Dr. Tanja Schirmeister Pharmazeutische Chemie Institut f\"ur Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland 97074 W\"urzburg Germany ; _publ_contact_author_email 'schirmei@pzlc.uni-wuerzburg.de' _publ_contact_author_fax '0049-931-8885494' _publ_contact_author_phone '0049-931-8885494' _publ_requested_journal 'ChemBioChem' _publ_section_title ; Electron Density Determination of Electrophilic Building Blocks as Model Compounds for Protease Inhibitors ; loop_ _publ_author_name ; 'Grabowsky, Simon' ; ; 'Pfeuffer, Thomas' ; ; 'Checinska, Lilianna' ; ; 'Weber, Manuela' ; ; 'Morgenroth, Wolfgang' ; ; 'Luger, Peter' ; ; 'Schirmeister, Tanja' ; _publ_author_address ; Institut f\"ur Chemie und Biochemie Kristallographie Freie Universit\"at Berlin Fabeckstr. 36a 14195 Berlin Germany ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _chemical_name_common 'substituted aziridine' _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O6' _chemical_formula_sum 'C12 H12 N2 O6' _chemical_formula_weight 280.24 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.013(2) _cell_length_b 13.312(3) _cell_length_c 13.652(2) _cell_angle_alpha 105.984(7) _cell_angle_beta 106.137(12) _cell_angle_gamma 107.137(9) _cell_volume 1231.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 9 _cell_measurement_reflns_used 3262 _cell_measurement_theta_min 17.5 _cell_measurement_theta_max 34.83 _exptl_crystal_description block _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'none' _diffrn_ambient_temperature 9 _diffrn_radiation_wavelength 0.56000 _diffrn_radiation_type 'synchrotron' _diffrn_measurement_device 'MarCCD 165 detector' _diffrn_measurement_method '\f' _diffrn_standards_decay_% 0 _diffrn_reflns_number 163095 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 34.83 _reflns_number_total 18463 _reflns_number_gt 15926 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_cell_refinement 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_data_reduction 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Koritsanszky et al, (2003)' _computing_molecular_graphics 'Koritsanszky et al, (2003)' _computing_publication_material 'Koritsanszky et al, (2003)' _publ_section_references ; Koritsanszky, T.; Howard, S.T.; Richter, T.; Macchi, P.; Volkov, A.; Gatti, C.; Mallinson, P.R.; Farrugia, L.; Su, Z.; and Hansen, N.K. (2003). XD - a computer program package for multipole refinement and topological analysis of charge densities from diffraction data ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w1=1/[s^2^(Fo)]' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15926 _refine_ls_number_parameters 612 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0241 _refine_ls_goodness_of_fit_ref 1.854 _refine_ls_shift/su_max 0.0000002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.843 _diffrn_reflns_theta_full 20.49 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.547 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.063 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O1 1.58316(4) 0.97373(3) 0.35151(2) 1.0000 0.008 O2 1.53013(4) 1.12282(3) 0.42069(2) 1.0000 0.008 O3 0.92024(4) 0.60617(2) 0.45680(2) 1.0000 0.007 O4 0.90335(4) 0.77335(2) 0.53675(2) 1.0000 0.004 O5 0.35260(4) 0.62119(2) 0.29423(2) 1.0000 0.005 O6 0.50106(4) 0.62173(2) 0.46119(2) 1.0000 0.005 O1A 0.34271(4) 0.93871(3) 1.11272(2) 1.0000 0.009 O2A 0.58980(4) 1.08182(3) 1.13794(2) 1.0000 0.007 O3A 0.56485(4) 0.59850(2) 0.73769(2) 1.0000 0.005 O4A 0.81758(4) 0.76680(2) 0.81732(2) 1.0000 0.004 O5A 1.09974(4) 0.56928(2) 0.92663(2) 1.0000 0.007 O6A 1.03713(4) 0.62987(2) 0.78678(2) 1.0000 0.005 N1 0.67632(5) 0.60823(3) 0.24643(3) 1.0000 0.004 N2 1.48021(5) 1.01907(3) 0.37815(2) 1.0000 0.004 N1A 0.74299(5) 0.55871(3) 0.93649(3) 1.0000 0.004 N2A 0.50365(4) 0.97988(3) 1.11538(2) 1.0000 0.004 C1 0.72354(5) 0.73034(3) 0.29023(3) 1.0000 0.004 C2 0.68307(4) 0.65987(3) 0.35723(3) 1.0000 0.003 C3 0.92245(5) 0.80555(3) 0.31583(2) 1.0000 0.004 C4 1.04748(4) 0.75783(3) 0.29143(3) 1.0000 0.005 C5 0.98456(4) 0.92432(3) 0.36405(3) 1.0000 0.005 C6 1.16850(4) 0.99522(3) 0.38634(3) 1.0000 0.005 C7 1.23108(4) 0.82768(3) 0.31134(3) 1.0000 0.005 C8 1.28736(4) 0.94499(3) 0.35770(2) 1.0000 0.004 C9 0.84725(4) 0.67330(3) 0.45378(3) 1.0000 0.003 C10 1.05879(4) 0.79796(3) 0.63638(3) 1.0000 0.006 C11 0.49387(4) 0.63329(2) 0.36693(3) 1.0000 0.003 C12 0.32162(5) 0.58915(3) 0.47433(3) 1.0000 0.008 C1A 0.86584(5) 0.67847(3) 1.00607(3) 1.0000 0.004 C2A 0.84322(4) 0.62778(3) 0.88747(3) 1.0000 0.003 C3A 0.77171(4) 0.75679(3) 1.03632(2) 1.0000 0.004 C4A 0.58740(4) 0.71371(3) 1.03231(3) 1.0000 0.005 C5A 0.86832(4) 0.87444(3) 1.06713(3) 1.0000 0.005 C6A 0.78148(4) 0.94856(3) 1.09272(3) 1.0000 0.005 C7A 0.50027(4) 0.78732(3) 1.06046(3) 1.0000 0.005 C8A 0.59839(4) 0.90308(3) 1.08956(2) 1.0000 0.004 C9A 0.72432(4) 0.65970(3) 0.80436(2) 1.0000 0.003 C10A 0.71120(5) 0.80779(3) 0.74542(3) 1.0000 0.007 C11A 1.00795(4) 0.60554(2) 0.86976(2) 1.0000 0.003 C12A 1.19561(5) 0.61365(3) 0.76277(3) 1.0000 0.008 H1 0.61360 0.76123 0.26171 1.0000 0.014(2) H4 0.99995 0.66607 0.25364 1.0000 0.017(2) H5 0.88984 0.96210 0.38454 1.0000 0.013(2) H6 1.21657 1.08699 0.42454 1.0000 0.017(2) H7 1.32804 0.79146 0.29174 1.0000 0.020(2) H10A 1.17650 0.79020 0.61814 1.0000 0.026(2) H10B 1.01442 0.74369 0.67707 1.0000 0.022(2) H10C 1.09257 0.88384 0.68701 1.0000 0.024(2) H12A 0.35647 0.58517 0.55403 1.0000 0.027(2) H12B 0.26418 0.65135 0.47025 1.0000 0.027(2) H12C 0.22442 0.50805 0.41094 1.0000 0.025(2) H1N 0.53868 0.56294 0.19492 1.0000 0.016(2) H1A 1.00487 0.69762 1.06772 1.0000 0.013(2) H4A 0.51361 0.62271 1.00760 1.0000 0.018(2) H5A 1.01006 0.90753 1.06853 1.0000 0.017(2) H6A 0.85252 1.03914 1.11403 1.0000 0.018(2) H7A 0.35786 0.75365 1.05797 1.0000 0.018(2) H10D 0.58449 0.80316 0.75848 1.0000 0.026(2) H10E 0.80430 0.89410 0.76929 1.0000 0.024(2) H10F 0.67902 0.75943 0.66104 1.0000 0.024(2) H12D 1.20905 0.53953 0.77314 1.0000 0.028(2) H12E 1.32200 0.68795 0.81589 1.0000 0.026(2) H12F 1.16312 0.60395 0.67863 1.0000 0.025(2) H1NA 0.81381 0.51070 0.95507 1.0000 0.013(2) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.00400(9) 0.00679(11) 0.01129(12) 0.00223(10) 0.00407(8) 0.00320(9) O2 0.0053(1) 0.0033(1) 0.0116(1) 0.0001(1) 0.0031(1) 0.0016(1) O3 0.00640(9) 0.00479(10) 0.00600(11) 0.00372(9) 0.00064(9) 0.00143(9) O4 0.00470(8) 0.00335(9) 0.00252(10) 0.00152(8) -0.00076(8) -0.00039(8) O5 0.00267(9) 0.00640(10) 0.00372(10) 0.00183(8) 0.00026(8) 0.00211(8) O6 0.00310(9) 0.00659(10) 0.00313(10) 0.00055(8) 0.00146(8) 0.00261(8) O1A 0.0043(1) 0.0075(1) 0.0113(1) 0.0029(1) 0.0044(1) 0.0030(1) O2A 0.0061(1) 0.0039(1) 0.0085(1) 0.0023(1) 0.0025(1) 0.0013(1) O3A 0.00312(9) 0.00373(10) 0.00595(10) -0.00052(9) -0.00117(8) 0.00206(8) O4A 0.00398(9) 0.00226(10) 0.00434(10) 0.00026(9) 0.00032(8) 0.00186(8) O5A 0.00543(9) 0.00810(11) 0.00571(10) 0.00464(9) 0.00260(8) 0.00496(9) O6A 0.00483(9) 0.00584(10) 0.00432(10) 0.00328(9) 0.00322(8) 0.00322(8) N1 0.0038(1) 0.0025(1) 0.0023(1) -0.0001(1) 0.0009(1) -0.0002(1) N2 0.0024(1) 0.0035(1) 0.0048(1) 0.0001(1) 0.0009(1) 0.0020(1) N1A 0.0038(1) 0.0028(1) 0.0040(1) 0.0009(1) 0.0018(1) 0.0019(1) N2A 0.0034(1) 0.0042(1) 0.0037(1) 0.0021(1) 0.0012(1) 0.0007(1) C1 0.0026(1) 0.0030(1) 0.0037(1) 0.0004(1) 0.0010(1) 0.0018(1) C2 0.0023(1) 0.0028(1) 0.0019(1) 0.0002(1) 0.0005(1) 0.0011(1) C3 0.0029(1) 0.0028(1) 0.0038(1) 0.0007(1) 0.0016(1) 0.0014(1) C4 0.0037(1) 0.0028(1) 0.0068(1) 0.0008(1) 0.0028(1) 0.0014(1) C5 0.0034(1) 0.0025(1) 0.0060(1) 0.0008(1) 0.0024(1) 0.0011(1) C6 0.0036(1) 0.0028(1) 0.0059(1) 0.0007(1) 0.0023(1) 0.0010(1) C7 0.0033(1) 0.0030(1) 0.0072(1) 0.0012(1) 0.0025(1) 0.0017(1) C8 0.0024(1) 0.0025(1) 0.0042(1) 0.0005(1) 0.0014(1) 0.0013(1) C9 0.00260(9) 0.00268(10) 0.00233(11) 0.00053(9) 0.00042(9) 0.00055(9) C10 0.0049(1) 0.0065(1) 0.0034(1) 0.0013(1) -0.0001(1) 0.0011(1) C11 0.0024(1) 0.0030(1) 0.0023(1) 0.0004(1) 0.0006(1) 0.0010(1) C12 0.0048(1) 0.0093(1) 0.0060(1) 0.0005(1) 0.0031(1) 0.0027(1) C1A 0.0035(1) 0.0036(1) 0.0024(1) 0.0016(1) 0.0006(1) 0.0003(1) C2A 0.0028(1) 0.0028(1) 0.0021(1) 0.0010(1) 0.0010(1) 0.0011(1) C3A 0.0030(1) 0.0031(1) 0.0033(1) 0.0010(1) 0.0013(1) 0.0003(1) C4A 0.0035(1) 0.0036(1) 0.0063(1) 0.0010(1) 0.0025(1) 0.0009(1) C5A 0.0031(1) 0.0033(1) 0.0058(1) 0.0008(1) 0.0019(1) 0.0003(1) C6A 0.0034(1) 0.0034(1) 0.0058(1) 0.0012(1) 0.0020(1) 0.0006(1) C7A 0.0032(1) 0.0040(1) 0.0062(1) 0.0011(1) 0.0022(1) 0.0010(1) C8A 0.0030(1) 0.0035(1) 0.0037(1) 0.0014(1) 0.0011(1) 0.0005(1) C9A 0.0026(1) 0.0019(1) 0.0029(1) 0.0003(1) 0.0006(1) 0.0010(1) C10A 0.0068(1) 0.0048(1) 0.0066(1) 0.0024(1) 0.0021(1) 0.0036(1) C11A 0.00309(9) 0.00337(10) 0.00281(11) 0.00153(9) 0.00137(8) 0.00159(9) C12A 0.0068(1) 0.0076(1) 0.0075(1) 0.0043(1) 0.0051(1) 0.0036(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.2314(6) . . yes O2 N2 1.2281(6) . . yes O3 C9 1.2072(6) . . yes O4 C9 1.3387(6) . . yes O4 C10 1.4426(6) . . yes O5 C11 1.2134(5) . . yes O6 C11 1.3252(5) . . yes O6 C12 1.4514(7) . . yes O1A N2A 1.2293(6) . . yes O2A N2A 1.2298(6) . . yes O3A C9A 1.2069(5) . . yes O4A C10A 1.4463(6) . . yes O4A C9A 1.3350(6) . . yes O5A C11A 1.2145(5) . . yes O6A C11A 1.3220(5) . . yes O6A C12A 1.4563(7) . . yes N1 C2 1.4572(6) . . yes N1 C1 1.4559(7) . . yes N2 C8 1.4659(7) . . yes N1 H1N 1.0089 . . no N1A C1A 1.4609(7) . . yes N1A C2A 1.4631(7) . . yes N2A C8A 1.4675(6) . . yes N1A H1NA 1.0089 . . yes C1 C3 1.4907(7) . . yes C1 C2 1.5100(7) . . yes C2 C11 1.5041(6) . . yes C2 C9 1.5059(6) . . yes C3 C5 1.4006(7) . . yes C3 C4 1.4008(7) . . yes C4 C7 1.3911(6) . . yes C5 C6 1.3887(6) . . yes C6 C8 1.3948(6) . . yes C7 C8 1.3873(6) . . yes C1 H1 1.0990 . . yes C4 H4 1.0830 . . yes C5 H5 1.0829 . . yes C6 H6 1.0830 . . yes C7 H7 1.0830 . . yes C10 H10C 1.0660 . . yes C10 H10A 1.0659 . . yes C10 H10B 1.0660 . . yes C12 H12C 1.0660 . . yes C12 H12A 1.0659 . . yes C12 H12B 1.0660 . . yes C1A C3A 1.4920(7) . . yes C1A C2A 1.5076(6) . . yes C2A C9A 1.5096(6) . . yes C2A C11A 1.5022(6) . . yes C3A C5A 1.4038(7) . . yes C3A C4A 1.3970(6) . . yes C4A C7A 1.3929(6) . . yes C5A C6A 1.3891(6) . . yes C6A C8A 1.3956(6) . . yes C7A C8A 1.3878(7) . . yes C1A H1A 1.0990 . . yes C4A H4A 1.0830 . . yes C5A H5A 1.0830 . . yes C6A H6A 1.0830 . . yes C7A H7A 1.0830 . . yes C10A H10D 1.0660 . . yes C10A H10E 1.0660 . . yes C10A H10F 1.0661 . . yes C12A H12D 1.0660 . . yes C12A H12E 1.0660 . . yes C12A H12F 1.0659 . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O4 C10 115.83(3) . . . yes C11 O6 C12 115.55(3) . . . yes C9A O4A C10A 114.80(3) . . . yes C11A O6A C12A 117.03(3) . . . yes C1 N1 C2 62.44(3) . . . yes O2 N2 C8 118.27(4) . . . yes O1 N2 O2 123.62(4) . . . yes O1 N2 C8 118.11(4) . . . yes C1 N1 H1N 112.03 . . . yes C2 N1 H1N 107.67 . . . yes C1A N1A C2A 62.07(3) . . . yes O1A N2A C8A 118.25(4) . . . yes O1A N2A O2A 123.78(4) . . . yes O2A N2A C8A 117.97(4) . . . yes C1A N1A H1NA 108.35 . . . yes C2A N1A H1NA 107.23 . . . yes C2 C1 C3 120.30(3) . . . yes N1 C1 C3 115.71(4) . . . yes N1 C1 C2 58.82(3) . . . yes N1 C2 C9 117.75(3) . . . yes C1 C2 C9 118.12(3) . . . yes C1 C2 C11 116.47(3) . . . yes C9 C2 C11 117.25(3) . . . yes N1 C2 C1 58.73(3) . . . yes N1 C2 C11 115.55(3) . . . yes C1 C3 C4 120.20(4) . . . yes C4 C3 C5 119.82(4) . . . yes C1 C3 C5 119.98(4) . . . yes C3 C4 C7 120.43(4) . . . yes C3 C5 C6 120.45(4) . . . yes C5 C6 C8 118.24(4) . . . yes C4 C7 C8 118.31(4) . . . yes N2 C8 C7 118.58(3) . . . yes N2 C8 C6 118.72(4) . . . yes C6 C8 C7 122.70(4) . . . yes O4 C9 C2 109.25(3) . . . yes O3 C9 O4 124.59(4) . . . yes O3 C9 C2 126.16(4) . . . yes O6 C11 C2 111.98(3) . . . yes O5 C11 C2 122.64(3) . . . yes O5 C11 O6 125.35(4) . . . yes N1 C1 H1 118.86 . . . yes C3 C1 H1 116.69 . . . yes C2 C1 H1 114.03 . . . yes C7 C4 H4 119.38 . . . yes C3 C4 H4 120.14 . . . yes C6 C5 H5 119.10 . . . yes C3 C5 H5 120.45 . . . yes C5 C6 H6 120.25 . . . yes C8 C6 H6 121.51 . . . yes C8 C7 H7 120.80 . . . yes C4 C7 H7 120.89 . . . yes H10A C10 H10B 111.32 . . . yes H10A C10 H10C 111.09 . . . yes O4 C10 H10B 110.48 . . . yes O4 C10 H10C 104.07 . . . yes H10B C10 H10C 109.09 . . . yes O4 C10 H10A 110.56 . . . yes O6 C12 H12A 104.35 . . . yes H12B C12 H12C 109.84 . . . yes H12A C12 H12B 111.35 . . . yes H12A C12 H12C 111.24 . . . yes O6 C12 H12B 110.34 . . . yes O6 C12 H12C 109.60 . . . yes C2A C1A C3A 119.48(3) . . . yes N1A C1A C2A 59.04(3) . . . yes N1A C1A C3A 117.19(4) . . . yes N1A C2A C11A 116.14(3) . . . yes C1A C2A C9A 117.45(3) . . . yes C1A C2A C11A 116.30(3) . . . yes C9A C2A C11A 118.14(3) . . . yes N1A C2A C1A 58.89(3) . . . yes N1A C2A C9A 116.46(3) . . . yes C1A C3A C4A 120.53(4) . . . yes C4A C3A C5A 119.90(4) . . . yes C1A C3A C5A 119.56(3) . . . yes C3A C4A C7A 120.21(4) . . . yes C3A C5A C6A 120.54(4) . . . yes C5A C6A C8A 118.16(4) . . . yes C4A C7A C8A 118.64(4) . . . yes N2A C8A C7A 118.50(3) . . . yes N2A C8A C6A 118.96(4) . . . yes C6A C8A C7A 122.52(4) . . . yes O3A C9A C2A 124.93(4) . . . yes O4A C9A C2A 110.54(3) . . . yes O3A C9A O4A 124.49(3) . . . yes O6A C11A C2A 111.93(3) . . . yes O5A C11A O6A 125.82(4) . . . yes O5A C11A C2A 122.26(3) . . . yes N1A C1A H1A 117.64 . . . yes C2A C1A H1A 114.53 . . . yes C3A C1A H1A 116.62 . . . yes C3A C4A H4A 119.30 . . . yes C7A C4A H4A 120.49 . . . yes C3A C5A H5A 119.84 . . . yes C6A C5A H5A 119.60 . . . yes C5A C6A H6A 121.36 . . . yes C8A C6A H6A 120.48 . . . yes C4A C7A H7A 119.97 . . . yes C8A C7A H7A 121.38 . . . yes O4A C10A H10D 109.96 . . . yes O4A C10A H10E 104.35 . . . yes O4A C10A H10F 110.30 . . . yes H10D C10A H10E 111.08 . . . yes H10D C10A H10F 110.69 . . . yes H10E C10A H10F 110.29 . . . yes O6A C12A H12D 111.09 . . . yes O6A C12A H12E 108.71 . . . yes O6A C12A H12F 105.21 . . . yes H12D C12A H12E 110.84 . . . yes H12D C12A H12F 110.47 . . . yes H12E C12A H12F 110.37 . . . yes 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 C10 O4 C9 O3 -1.85(6) . . . . yes C10 O4 C9 C2 179.11(3) . . . . yes C12 O6 C11 O5 1.59(5) . . . . yes C12 O6 C11 C2 -176.42(3) . . . . yes C10A O4A C9A O3A 1.12(5) . . . . yes C10A O4A C9A C2A -176.70(3) . . . . yes C12A O6A C11A O5A -1.17(5) . . . . yes C12A O6A C11A C2A 178.95(3) . . . . yes C2 N1 C1 C3 111.30(4) . . . . yes C1 N1 C2 C11 106.72(4) . . . . yes C1 N1 C2 C9 -107.68(4) . . . . yes O2 N2 C8 C7 -178.96(3) . . . . yes O2 N2 C8 C6 0.58(4) . . . . yes O1 N2 C8 C7 1.16(4) . . . . yes O1 N2 C8 C6 -179.30(3) . . . . yes C2A N1A C1A C3A 109.69(4) . . . . yes C1A N1A C2A C11A 106.28(4) . . . . yes C1A N1A C2A C9A -107.52(4) . . . . yes O1A N2A C8A C6A -179.70(3) . . . . yes O2A N2A C8A C6A 0.64(4) . . . . yes O2A N2A C8A C7A -177.93(3) . . . . yes O1A N2A C8A C7A 1.72(4) . . . . yes C2 C1 C3 C5 -109.04(4) . . . . yes C3 C1 C2 C9 3.53(5) . . . . yes N1 C1 C3 C5 -176.45(3) . . . . yes C2 C1 C3 C4 71.20(4) . . . . yes N1 C1 C2 C9 107.04(4) . . . . yes N1 C1 C2 C11 -105.15(4) . . . . yes C3 C1 C2 N1 -103.52(4) . . . . yes C3 C1 C2 C11 151.33(4) . . . . yes N1 C1 C3 C4 3.78(5) . . . . yes C11 C2 C9 O4 -74.01(4) . . . . yes N1 C2 C11 O6 143.57(4) . . . . yes C1 C2 C9 O3 -105.48(5) . . . . yes N1 C2 C9 O3 -38.05(6) . . . . yes N1 C2 C9 O4 140.98(4) . . . . yes C1 C2 C9 O4 73.55(4) . . . . yes C11 C2 C9 O3 106.96(5) . . . . yes N1 C2 C11 O5 -34.51(5) . . . . yes C1 C2 C11 O6 -150.29(3) . . . . yes C9 C2 C11 O5 179.72(4) . . . . yes C1 C2 C11 O5 31.63(5) . . . . yes C9 C2 C11 O6 -2.20(5) . . . . yes C4 C3 C5 C6 0.97(5) . . . . yes C1 C3 C5 C6 -178.79(3) . . . . yes C1 C3 C4 C7 177.60(3) . . . . yes C5 C3 C4 C7 -2.17(5) . . . . yes C3 C4 C7 C8 1.24(5) . . . . yes C3 C5 C6 C8 1.09(5) . . . . yes C5 C6 C8 N2 178.41(3) . . . . yes C5 C6 C8 C7 -2.07(5) . . . . yes C4 C7 C8 N2 -179.57(3) . . . . yes C4 C7 C8 C6 0.91(5) . . . . yes C3A C1A C2A C11A 148.15(4) . . . . yes N1A C1A C3A C4A 21.52(5) . . . . yes N1A C1A C3A C5A -157.35(3) . . . . yes N1A C1A C2A C9A 105.84(4) . . . . yes N1A C1A C2A C11A -106.00(4) . . . . yes C3A C1A C2A N1A -105.84(4) . . . . yes C3A C1A C2A C9A 0.00(6) . . . . yes C2A C1A C3A C4A 89.56(5) . . . . yes C2A C1A C3A C5A -89.31(4) . . . . yes N1A C2A C11A O5A -27.41(5) . . . . yes C11A C2A C9A O3A 108.27(4) . . . . yes C11A C2A C9A O4A -73.92(4) . . . . yes N1A C2A C9A O3A -37.23(5) . . . . yes N1A C2A C9A O4A 140.58(4) . . . . yes C1A C2A C9A O3A -104.17(4) . . . . yes C1A C2A C9A O4A 73.64(4) . . . . yes C1A C2A C11A O5A 39.04(5) . . . . yes C1A C2A C11A O6A -141.07(3) . . . . yes N1A C2A C11A O6A 152.47(3) . . . . yes C9A C2A C11A O6A 6.86(4) . . . . yes C9A C2A C11A O5A -173.02(3) . . . . yes C5A C3A C4A C7A -1.01(5) . . . . yes C1A C3A C4A C7A -179.87(3) . . . . yes C4A C3A C5A C6A -0.63(5) . . . . yes C1A C3A C5A C6A 178.25(3) . . . . yes C3A C4A C7A C8A 1.62(5) . . . . yes C3A C5A C6A C8A 1.57(5) . . . . yes C5A C6A C8A C7A -0.95(5) . . . . yes C5A C6A C8A N2A -179.47(3) . . . . yes C4A C7A C8A C6A -0.64(5) . . . . yes C4A C7A C8A N2A 177.88(3) . . . . yes data_Aziridin_conventional _publ_contact_author ; Prof. Dr. Peter Luger Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany ; _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_author_fax '0049-30-838-53464' _publ_contact_author_phone '0049-30-838-53411' _publ_requested_journal 'Organo and Biomolecular Chemistry' _publ_section_title ; A Comparative Study on the Experimentally Derived Electron Densities of three Protease Inhibitor Model Compounds ; loop_ _publ_author_name ; Grabowsky, Simon ; ; Pfeuffer, Thomas ; ; Morgenroth, Wolfgang ; ; Paulmann, Carsten ; ; Schirmeister, Tanja ; ; Luger, Peter ; _publ_author_address ; Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany and Universit\"at W\"urzburg Institut f\"ur Pharmazie und Lebensmittelchemie Am Hubland 97074 W/"urzburg Germany ; _chemical_name_common 'acceptor-substituted aziridine' _chemical_formula_moiety 'C12 H12 N2 O6' _chemical_formula_sum 'C12 H12 N2 O6' _chemical_formula_weight 280.24 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 8.0274(16) _cell_length_b 13.333(3) _cell_length_c 13.674(3) _cell_angle_alpha 105.97(3) _cell_angle_beta 106.05(3) _cell_angle_gamma 107.14(3) _cell_volume 1238.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 27(2) _cell_measurement_reflns_used 987 _cell_measurement_theta_min 26.29 _cell_measurement_theta_max 52.33 _exptl_crystal_description block _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type 'none' _diffrn_ambient_temperature 27(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 113442 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 51.43 _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 40.25 _diffrn_measured_fraction_theta_full 0.952 _reflns_number_total 23550 _reflns_number_gt 16994 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'SMART, Bruker-AXS inc., 1996, Madison, WI(USA)' _computing_cell_refinement 'SAINT, Bruker-AXS inc., 1994-1996, Madison, WI(USA)' _computing_data_reduction 'SORTAV Blessing, R. J. Appl. Cryst. 22, 396 (1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_number_reflns 16994 _refine_ls_number_parameters 603 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.033 _refine_ls_R_factor_all 0.052 _refine_ls_R_Fsqd_factor 0.045 _refine_ls_wR_factor_ref 0.039 _refine_ls_goodness_of_fit_ref 1.426 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.455 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.071 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O1 1.58312(7) 0.97409(5) 0.35172(5) 1 2 0.015 O2 1.53002(7) 1.12269(5) 0.42073(5) 1 2 0.015 O3 0.91992(6) 0.60617(4) 0.45643(4) 1 2 0.012 O4 0.90334(6) 0.77316(4) 0.53653(3) 1 2 0.009 O5 0.35335(6) 0.62169(4) 0.29438(4) 1 2 0.010 O6 0.50117(6) 0.62180(4) 0.46109(3) 1 2 0.010 O1A 0.34277(8) 0.93848(6) 1.11267(5) 1 2 0.016 O2A 0.58931(8) 1.08130(5) 1.13803(4) 1 2 0.014 O3A 0.56524(6) 0.59843(4) 0.73784(4) 1 2 0.011 O4A 0.81743(6) 0.76667(4) 0.81744(3) 1 2 0.009 O5A 1.09949(6) 0.56953(4) 0.92675(4) 1 2 0.011 O6A 1.03700(6) 0.62966(4) 0.78688(3) 1 2 0.009 N1 0.67659(7) 0.60847(4) 0.24636(4) 1 2 0.009 N2 1.48014(6) 1.01910(5) 0.37816(4) 1 2 0.009 N1A 0.74291(7) 0.55868(4) 0.93655(4) 1 2 0.009 N2A 0.50350(7) 0.97962(5) 1.11538(4) 1 2 0.011 C1 0.72370(7) 0.73059(4) 0.29023(4) 1 2 0.008 C2 0.68324(6) 0.66004(4) 0.35709(4) 1 2 0.007 C3 0.92255(7) 0.80566(4) 0.31580(4) 1 2 0.008 C4 1.04759(7) 0.75814(5) 0.29147(4) 1 2 0.009 C5 0.98459(7) 0.92431(4) 0.36397(4) 1 2 0.009 C6 1.16862(7) 0.99524(4) 0.38627(4) 1 2 0.009 C7 1.23116(7) 0.82798(5) 0.31145(4) 1 2 0.010 C8 1.28736(7) 0.94522(4) 0.35783(4) 1 2 0.008 C9 0.84738(6) 0.67321(4) 0.45364(4) 1 2 0.008 C10 1.05850(7) 0.79754(5) 0.63604(4) 1 2 0.011 C11 0.49417(6) 0.63338(4) 0.36686(4) 1 2 0.008 C12 0.32195(8) 0.58932(5) 0.47436(5) 1 2 0.013 C1A 0.86534(7) 0.67825(5) 1.00601(4) 1 2 0.009 C2A 0.84319(6) 0.62759(4) 0.88759(4) 1 2 0.007 C3A 0.77127(7) 0.75659(5) 1.03625(4) 1 2 0.009 C4A 0.58730(7) 0.71354(5) 1.03224(4) 1 2 0.010 C5A 0.86811(7) 0.87401(5) 1.06715(4) 1 2 0.010 C6A 0.78113(7) 0.94830(5) 1.09281(4) 1 2 0.010 C7A 0.50002(7) 0.78712(5) 1.06039(4) 1 2 0.011 C8A 0.59832(7) 0.90272(5) 1.08951(4) 1 2 0.009 C9A 0.72428(6) 0.65952(4) 0.80443(4) 1 2 0.007 C10A 0.71111(8) 0.80760(5) 0.74554(5) 1 2 0.011 C11A 1.00772(6) 0.60545(4) 0.86982(4) 1 2 0.008 C12A 1.19556(8) 0.61363(5) 0.76292(5) 1 2 0.012 H1 0.615067 0.762052 0.26147 1 2 0.018(5) H4 0.999927 0.666442 0.255078 1 2 0.015(4) H5 0.889398 0.960526 0.386038 1 2 0.013(4) H6 1.222156 1.087145 0.424772 1 2 0.020(4) H7 1.327298 0.791652 0.291069 1 2 0.017(4) H10A 1.178891 0.790364 0.621215 1 2 0.030(5) H10B 1.00846 0.739847 0.672275 1 2 0.033(5) H10C 1.095381 0.883522 0.687327 1 2 0.026(4) H12A 0.354134 0.586406 0.554312 1 2 0.029(5) H12B 0.266737 0.652363 0.470613 1 2 0.032(5) H12C 0.224356 0.508983 0.410457 1 2 0.031(5) H1N 0.540349 0.562038 0.19367 1 2 0.013(4) H1A 1.004246 0.69742 1.067255 1 2 0.020(5) H4A 0.516034 0.622379 1.006743 1 2 0.017(4) H5A 1.009841 0.910126 1.069748 1 2 0.019(4) H6A 0.850118 1.038847 1.113975 1 2 0.014(4) H7A 0.357717 0.754589 1.057929 1 2 0.010(3) H10D 0.58543 0.805414 0.75865 1 2 0.030(5) H10E 0.806114 0.891783 0.764282 1 2 0.033(5) H10F 0.671651 0.75945 0.660254 1 2 0.028(5) H12D 1.214641 0.542199 0.776849 1 2 0.037(6) H12E 1.318905 0.690417 0.81214 1 2 0.029(5) H12F 1.154591 0.597474 0.677134 1 2 0.028(5) H1NA 0.812189 0.510968 0.957681 1 2 0.014(5) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.00938(14) 0.0145(2) 0.0215(2) 0.00553(13) 0.00766(13) 0.00697(14) O2 0.01050(15) 0.00983(17) 0.02114(19) 0.00231(12) 0.00584(13) 0.00481(13) O3 0.01166(13) 0.01029(15) 0.01280(14) 0.00710(12) 0.00301(12) 0.00366(12) O4 0.01000(12) 0.00845(14) 0.00813(12) 0.00468(10) 0.00179(10) 0.00209(10) O5 0.00790(12) 0.01140(16) 0.01017(12) 0.00494(9) 0.00299(10) 0.00434(10) O6 0.00763(12) 0.01276(16) 0.00877(12) 0.00327(9) 0.00380(10) 0.00481(10) O1A 0.01139(15) 0.0183(2) 0.0213(2) 0.00892(15) 0.00839(14) 0.00625(15) O2A 0.01390(16) 0.01248(18) 0.01589(17) 0.00769(14) 0.00502(13) 0.00339(12) O3A 0.00803(12) 0.00915(14) 0.01163(13) 0.00213(10) 0.00052(11) 0.00414(10) O4A 0.00900(12) 0.00728(13) 0.00948(12) 0.00283(10) 0.00210(10) 0.00359(9) O5A 0.01109(13) 0.01467(17) 0.01286(14) 0.00821(12) 0.00553(11) 0.00829(13) O6A 0.01040(12) 0.01166(15) 0.01011(12) 0.00683(11) 0.00613(10) 0.00568(11) N1 0.00873(14) 0.00817(16) 0.00813(13) 0.00327(11) 0.00368(11) 0.00207(11) N2 0.00735(13) 0.00960(17) 0.01214(15) 0.00347(12) 0.00375(11) 0.00508(11) N1A 0.00896(14) 0.00910(16) 0.01011(14) 0.00410(12) 0.00427(12) 0.00493(12) N2A 0.00941(14) 0.01283(19) 0.01004(14) 0.00657(13) 0.00362(11) 0.00304(11) C1 0.00765(13) 0.00837(16) 0.00912(14) 0.00363(11) 0.00378(11) 0.00412(12) C2 0.00714(13) 0.00775(15) 0.00754(13) 0.00322(11) 0.00306(11) 0.00314(11) C3 0.00777(13) 0.00757(15) 0.00922(14) 0.00349(11) 0.00412(11) 0.00376(11) C4 0.00881(14) 0.00771(16) 0.01261(16) 0.00383(12) 0.00522(12) 0.00365(12) C5 0.00869(14) 0.00764(16) 0.01127(15) 0.00402(12) 0.00496(12) 0.00343(11) C6 0.00863(14) 0.00735(16) 0.01201(15) 0.00349(11) 0.00467(12) 0.00339(12) C7 0.00882(14) 0.00870(17) 0.01350(16) 0.00471(12) 0.00555(12) 0.00458(12) C8 0.00755(13) 0.00878(16) 0.01001(14) 0.00358(11) 0.00389(11) 0.00423(11) C9 0.00722(12) 0.00749(15) 0.00826(13) 0.00347(11) 0.00293(10) 0.00312(11) C10 0.00991(14) 0.01267(18) 0.00904(14) 0.00385(13) 0.00201(12) 0.00389(12) C11 0.00685(12) 0.00777(15) 0.00821(13) 0.00322(10) 0.00309(10) 0.00302(10) C12 0.00935(15) 0.0163(2) 0.01211(17) 0.00295(13) 0.00570(13) 0.00521(14) C1A 0.00840(14) 0.01050(18) 0.00750(14) 0.00463(12) 0.00298(12) 0.00306(12) C2A 0.00738(13) 0.00774(15) 0.00747(13) 0.00390(11) 0.00313(11) 0.00320(11) C3A 0.00785(13) 0.00975(16) 0.00807(14) 0.00410(12) 0.00327(11) 0.00256(11) C4A 0.00872(14) 0.01056(18) 0.01176(16) 0.00421(12) 0.00489(12) 0.00371(12) C5A 0.00789(13) 0.00936(17) 0.01125(15) 0.00380(12) 0.00401(11) 0.00200(12) C6A 0.00882(14) 0.00988(18) 0.01092(15) 0.00400(12) 0.00387(12) 0.00215(12) C7A 0.00801(14) 0.01174(19) 0.01178(16) 0.00441(12) 0.00455(12) 0.00328(12) C8A 0.00810(13) 0.01143(18) 0.00897(15) 0.00516(13) 0.00336(11) 0.00262(12) C9A 0.00716(12) 0.00703(15) 0.00745(12) 0.00325(11) 0.00250(10) 0.00275(10) C10A 0.01221(15) 0.01002(17) 0.01227(16) 0.00550(13) 0.00439(13) 0.00593(13) C11A 0.00795(12) 0.00843(15) 0.00884(13) 0.00471(11) 0.00380(11) 0.00395(11) C12A 0.01315(16) 0.01318(19) 0.01414(17) 0.00827(14) 0.00859(14) 0.00611(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.2298(7) 1_555 1_555 yes O2 N2 1.2287(8) 1_555 1_555 yes O3 C9 1.2052(7) 1_555 1_555 yes O4 C9 1.3405(7) 1_555 1_555 yes O4 C10 1.4453(7) 1_555 1_555 yes O5 C11 1.2148(6) 1_555 1_555 yes O6 C11 1.3273(6) 1_555 1_555 yes O6 C12 1.4528(7) 1_555 1_555 yes O1A N2A 1.2298(7) 1_555 1_555 yes O2A N2A 1.2284(8) 1_555 1_555 yes O3A C9A 1.2077(6) 1_555 1_555 yes O4A C9A 1.3374(6) 1_555 1_555 yes O4A C10A 1.4486(7) 1_555 1_555 yes O5A C11A 1.2140(6) 1_555 1_555 yes O6A C11A 1.3228(6) 1_555 1_555 yes O6A C12A 1.4580(7) 1_555 1_555 yes N1 C1 1.4588(7) 1_555 1_555 yes N1 C2 1.4590(7) 1_555 1_555 yes N1 H1N 1.0090 1_555 1_555 yes N2 C8 1.4681(7) 1_555 1_555 yes N1A C1A 1.4618(7) 1_555 1_555 yes N1A C2A 1.4631(7) 1_555 1_555 yes N1A H1NA 1.0090 1_555 1_555 yes N2A C8A 1.4714(7) 1_555 1_555 yes C1 C2 1.5110(7) 1_555 1_555 yes C1 C3 1.4930(7) 1_555 1_555 yes C1 H1 1.0990 1_555 1_555 yes C2 C9 1.5112(6) 1_555 1_555 yes C2 C11 1.5061(7) 1_555 1_555 yes C3 C4 1.4011(7) 1_555 1_555 yes C3 C5 1.4019(7) 1_555 1_555 yes C4 C7 1.3935(7) 1_555 1_555 yes C4 H4 1.0830 1_555 1_555 yes C5 C6 1.3923(7) 1_555 1_555 yes C5 H5 1.0830 1_555 1_555 yes C6 C8 1.3935(7) 1_555 1_555 yes C6 H6 1.0830 1_555 1_555 yes C7 C8 1.3891(7) 1_555 1_555 yes C7 H7 1.0830 1_555 1_555 yes C10 H10A 1.0660 1_555 1_555 yes C10 H10B 1.0660 1_555 1_555 yes C10 H10C 1.0660 1_555 1_555 yes C12 H12A 1.0660 1_555 1_555 yes C12 H12B 1.0660 1_555 1_555 yes C12 H12C 1.0660 1_555 1_555 yes C1A C2A 1.5093(7) 1_555 1_555 yes C1A C3A 1.4940(7) 1_555 1_555 yes C1A H1A 1.0990 1_555 1_555 yes C2A C9A 1.5136(7) 1_555 1_555 yes C2A C11A 1.5027(7) 1_555 1_555 yes C3A C4A 1.3970(7) 1_555 1_555 yes C3A C5A 1.4039(8) 1_555 1_555 yes C4A C7A 1.3957(8) 1_555 1_555 yes C4A H4A 1.0830 1_555 1_555 yes C5A C6A 1.3942(8) 1_555 1_555 yes C5A H5A 1.0830 1_555 1_555 yes C6A C8A 1.3955(7) 1_555 1_555 yes C6A H6A 1.0830 1_555 1_555 yes C7A C8A 1.3888(8) 1_555 1_555 yes C7A H7A 1.0830 1_555 1_555 yes C10A H10D 1.0660 1_555 1_555 yes C10A H10E 1.0660 1_555 1_555 yes C10A H10F 1.0660 1_555 1_555 yes C12A H12D 1.0660 1_555 1_555 yes C12A H12E 1.0660 1_555 1_555 yes C12A H12F 1.0660 1_555 1_555 yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O4 C10 115.80(4) 1_555 1_555 1_555 yes C11 O6 C12 115.58(4) 1_555 1_555 1_555 yes C9A O4A C10A 114.73(4) 1_555 1_555 1_555 yes C11A O6A C12A 117.09(4) 1_555 1_555 1_555 yes C1 N1 C2 62.38(3) 1_555 1_555 1_555 yes C1 N1 H1N 113.14 1_555 1_555 1_555 yes C2 N1 H1N 109.06 1_555 1_555 1_555 yes O1 N2 O2 123.48(6) 1_555 1_555 1_555 yes O1 N2 C8 118.31(5) 1_555 1_555 1_555 yes O2 N2 C8 118.21(5) 1_555 1_555 1_555 yes C1A N1A C2A 62.13(3) 1_555 1_555 1_555 yes C1A N1A H1NA 107.98 1_555 1_555 1_555 yes C2A N1A H1NA 109.03 1_555 1_555 1_555 yes O1A N2A O2A 123.74(6) 1_555 1_555 1_555 yes O1A N2A C8A 118.23(6) 1_555 1_555 1_555 yes O2A N2A C8A 118.04(5) 1_555 1_555 1_555 yes N1 C1 C2 58.82(3) 1_555 1_555 1_555 yes N1 C1 C3 115.64(4) 1_555 1_555 1_555 yes N1 C1 H1 119.18 1_555 1_555 1_555 yes C2 C1 C3 120.22(4) 1_555 1_555 1_555 yes C2 C1 H1 114.72 1_555 1_555 1_555 yes C3 C1 H1 116.18 1_555 1_555 1_555 yes N1 C2 C1 58.80(3) 1_555 1_555 1_555 yes N1 C2 C9 117.74(4) 1_555 1_555 1_555 yes N1 C2 C11 115.51(4) 1_555 1_555 1_555 yes C1 C2 C9 118.19(4) 1_555 1_555 1_555 yes C1 C2 C11 116.47(4) 1_555 1_555 1_555 yes C9 C2 C11 117.23(4) 1_555 1_555 1_555 yes C1 C3 C4 120.32(5) 1_555 1_555 1_555 yes C1 C3 C5 119.96(4) 1_555 1_555 1_555 yes C4 C3 C5 119.72(4) 1_555 1_555 1_555 yes C3 C4 C7 120.48(5) 1_555 1_555 1_555 yes C3 C4 H4 119.64 1_555 1_555 1_555 yes C7 C4 H4 119.86 1_555 1_555 1_555 yes C3 C5 C6 120.48(5) 1_555 1_555 1_555 yes C3 C5 H5 119.44 1_555 1_555 1_555 yes C6 C5 H5 120.06 1_555 1_555 1_555 yes C5 C6 C8 118.28(5) 1_555 1_555 1_555 yes C5 C6 H6 122.49 1_555 1_555 1_555 yes C8 C6 H6 119.23 1_555 1_555 1_555 yes C4 C7 C8 118.33(5) 1_555 1_555 1_555 yes C4 C7 H7 120.75 1_555 1_555 1_555 yes C8 C7 H7 120.91 1_555 1_555 1_555 yes N2 C8 C6 118.85(5) 1_555 1_555 1_555 yes N2 C8 C7 118.50(5) 1_555 1_555 1_555 yes C6 C8 C7 122.65(5) 1_555 1_555 1_555 yes O3 C9 O4 124.67(5) 1_555 1_555 1_555 yes O3 C9 C2 126.13(5) 1_555 1_555 1_555 yes O4 C9 C2 109.19(4) 1_555 1_555 1_555 yes O4 C10 H10A 112.90 1_555 1_555 1_555 yes O4 C10 H10B 107.71 1_555 1_555 1_555 yes O4 C10 H10C 105.11 1_555 1_555 1_555 yes H10A C10 H10B 110.18 1_555 1_555 1_555 yes H10A C10 H10C 109.13 1_555 1_555 1_555 yes H10B C10 H10C 111.74 1_555 1_555 1_555 yes O5 C11 O6 125.39(5) 1_555 1_555 1_555 yes O5 C11 C2 122.58(4) 1_555 1_555 1_555 yes O6 C11 C2 112.01(4) 1_555 1_555 1_555 yes O6 C12 H12A 105.51 1_555 1_555 1_555 yes O6 C12 H12B 109.53 1_555 1_555 1_555 yes O6 C12 H12C 109.59 1_555 1_555 1_555 yes H12A C12 H12B 109.96 1_555 1_555 1_555 yes H12A C12 H12C 112.31 1_555 1_555 1_555 yes H12B C12 H12C 109.82 1_555 1_555 1_555 yes N1A C1A C2A 58.98(3) 1_555 1_555 1_555 yes N1A C1A C3A 117.25(4) 1_555 1_555 1_555 yes N1A C1A H1A 117.68 1_555 1_555 1_555 yes C2A C1A C3A 119.55(4) 1_555 1_555 1_555 yes C2A C1A H1A 114.26 1_555 1_555 1_555 yes C3A C1A H1A 116.69 1_555 1_555 1_555 yes N1A C2A C1A 58.89(3) 1_555 1_555 1_555 yes N1A C2A C9A 116.37(4) 1_555 1_555 1_555 yes N1A C2A C11A 116.25(4) 1_555 1_555 1_555 yes C1A C2A C9A 117.38(4) 1_555 1_555 1_555 yes C1A C2A C11A 116.39(4) 1_555 1_555 1_555 yes C9A C2A C11A 118.11(4) 1_555 1_555 1_555 yes C1A C3A C4A 120.47(5) 1_555 1_555 1_555 yes C1A C3A C5A 119.47(4) 1_555 1_555 1_555 yes C4A C3A C5A 120.06(5) 1_555 1_555 1_555 yes C3A C4A C7A 120.21(5) 1_555 1_555 1_555 yes C3A C4A H4A 118.05 1_555 1_555 1_555 yes C7A C4A H4A 121.74 1_555 1_555 1_555 yes C3A C5A C6A 120.43(5) 1_555 1_555 1_555 yes C3A C5A H5A 122.03 1_555 1_555 1_555 yes C6A C5A H5A 117.52 1_555 1_555 1_555 yes C5A C6A C8A 118.05(5) 1_555 1_555 1_555 yes C5A C6A H6A 122.18 1_555 1_555 1_555 yes C8A C6A H6A 119.77 1_555 1_555 1_555 yes C4A C7A C8A 118.50(5) 1_555 1_555 1_555 yes C4A C7A H7A 120.75 1_555 1_555 1_555 yes C8A C7A H7A 120.74 1_555 1_555 1_555 yes N2A C8A C6A 118.86(5) 1_555 1_555 1_555 yes N2A C8A C7A 118.40(5) 1_555 1_555 1_555 yes C6A C8A C7A 122.73(5) 1_555 1_555 1_555 yes O3A C9A O4A 124.49(5) 1_555 1_555 1_555 yes O3A C9A C2A 124.99(5) 1_555 1_555 1_555 yes O4A C9A C2A 110.48(4) 1_555 1_555 1_555 yes O4A C10A H10D 111.15 1_555 1_555 1_555 yes O4A C10A H10E 105.10 1_555 1_555 1_555 yes O4A C10A H10F 112.71 1_555 1_555 1_555 yes H10D C10A H10E 112.54 1_555 1_555 1_555 yes H10D C10A H10F 108.03 1_555 1_555 1_555 yes H10E C10A H10F 107.31 1_555 1_555 1_555 yes O5A C11A O6A 125.79(5) 1_555 1_555 1_555 yes O5A C11A C2A 122.20(4) 1_555 1_555 1_555 yes O6A C11A C2A 112.01(4) 1_555 1_555 1_555 yes O6A C12A H12D 111.72 1_555 1_555 1_555 yes O6A C12A H12E 108.14 1_555 1_555 1_555 yes O6A C12A H12F 103.64 1_555 1_555 1_555 yes H12D C12A H12E 111.77 1_555 1_555 1_555 yes H12D C12A H12F 109.55 1_555 1_555 1_555 yes H12E C12A H12F 111.74 1_555 1_555 1_555 yes 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 C10 O4 C9 O3 -1.90(5) 1_555 1_555 1_555 1_555 yes C10 O4 C9 C2 179.11(6) 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10A 53.46 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10B -68.41 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10C 172.31 1_555 1_555 1_555 1_555 yes C12 O6 C11 O5 1.81(5) 1_555 1_555 1_555 1_555 yes C12 O6 C11 C2 -176.51(6) 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12A -178.37 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12B -60.05 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12C 60.50 1_555 1_555 1_555 1_555 yes C10A O4A C9A O3A 1.11(5) 1_555 1_555 1_555 1_555 yes C10A O4A C9A C2A -176.72(6) 1_555 1_555 1_555 1_555 yes C9A O4A C10A H10D 59.95 1_555 1_555 1_555 1_555 yes C9A O4A C10A H10E -178.04 1_555 1_555 1_555 1_555 yes C9A O4A C10A H10F -61.49 1_555 1_555 1_555 1_555 yes C12A O6A C11A O5A -1.11(5) 1_555 1_555 1_555 1_555 yes C12A O6A C11A C2A 178.87(6) 1_555 1_555 1_555 1_555 yes C11A O6A C12A H12D 35.27 1_555 1_555 1_555 1_555 yes C11A O6A C12A H12E -88.14 1_555 1_555 1_555 1_555 yes C11A O6A C12A H12F 153.13 1_555 1_555 1_555 1_555 yes C2 N1 C1 C3 111.23(5) 1_555 1_555 1_555 1_555 yes C1 N1 C2 C9 -107.79(5) 1_555 1_555 1_555 1_555 yes C1 N1 C2 C11 106.76(5) 1_555 1_555 1_555 1_555 yes C2 N1 C1 H1 -102.83 1_555 1_555 1_555 1_555 yes H1N N1 C1 C2 100.21 1_555 1_555 1_555 1_555 yes H1N N1 C1 C3 -148.56 1_555 1_555 1_555 1_555 yes H1N N1 C1 H1 -2.62 1_555 1_555 1_555 1_555 yes H1N N1 C2 C1 -106.76 1_555 1_555 1_555 1_555 yes H1N N1 C2 C9 145.45 1_555 1_555 1_555 1_555 yes H1N N1 C2 C11 0.00 1_555 1_555 1_555 1_555 yes O1 N2 C8 C6 -179.27(8) 1_555 1_555 1_555 1_555 yes O1 N2 C8 C7 1.08(5) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C6 0.73(5) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C7 -178.92(8) 1_555 1_555 1_555 1_555 yes C2A N1A C1A C3A 109.73(5) 1_555 1_555 1_555 1_555 yes C1A N1A C2A C9A -107.48(5) 1_555 1_555 1_555 1_555 yes C1A N1A C2A C11A 106.34(5) 1_555 1_555 1_555 1_555 yes C2A N1A C1A H1A -103.06 1_555 1_555 1_555 1_555 yes H1NA N1A C1A C2A 102.49 1_555 1_555 1_555 1_555 yes H1NA N1A C1A C3A -147.78 1_555 1_555 1_555 1_555 yes H1NA N1A C1A H1A -0.57 1_555 1_555 1_555 1_555 yes H1NA N1A C2A C1A -100.77 1_555 1_555 1_555 1_555 yes H1NA N1A C2A C9A 151.75 1_555 1_555 1_555 1_555 yes H1NA N1A C2A C11A 5.56 1_555 1_555 1_555 1_555 yes O1A N2A C8A C6A -179.67(8) 1_555 1_555 1_555 1_555 yes O1A N2A C8A C7A 1.72(6) 1_555 1_555 1_555 1_555 yes O2A N2A C8A C6A 0.62(5) 1_555 1_555 1_555 1_555 yes O2A N2A C8A C7A -177.99(8) 1_555 1_555 1_555 1_555 yes N1 C1 C2 C9 107.02(5) 1_555 1_555 1_555 1_555 yes N1 C1 C2 C11 -105.12(5) 1_555 1_555 1_555 1_555 yes N1 C1 C3 C4 3.77(5) 1_555 1_555 1_555 1_555 yes N1 C1 C3 C5 -176.50(7) 1_555 1_555 1_555 1_555 yes C3 C1 C2 N1 -103.47(5) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C4 71.12(6) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C5 -109.14(6) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C9 3.56(4) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C11 151.41(7) 1_555 1_555 1_555 1_555 yes H1 C1 C2 N1 110.41 1_555 1_555 1_555 1_555 yes H1 C1 C2 C9 -142.57 1_555 1_555 1_555 1_555 yes H1 C1 C2 C11 5.29 1_555 1_555 1_555 1_555 yes H1 C1 C3 C4 -143.22 1_555 1_555 1_555 1_555 yes H1 C1 C3 C5 36.51 1_555 1_555 1_555 1_555 yes N1 C2 C9 O3 -37.95(6) 1_555 1_555 1_555 1_555 yes N1 C2 C9 O4 141.02(6) 1_555 1_555 1_555 1_555 yes N1 C2 C11 O5 -34.77(5) 1_555 1_555 1_555 1_555 yes N1 C2 C11 O6 143.60(6) 1_555 1_555 1_555 1_555 yes C1 C2 C9 O3 -105.48(7) 1_555 1_555 1_555 1_555 yes C1 C2 C9 O4 73.49(5) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O5 31.43(5) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O6 -150.20(6) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O3 106.90(7) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O4 -74.13(5) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O5 179.60(7) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O6 -2.03(4) 1_555 1_555 1_555 1_555 yes C1 C3 C4 C7 177.63(8) 1_555 1_555 1_555 1_555 yes C1 C3 C4 H4 -0.93 1_555 1_555 1_555 1_555 yes C1 C3 C5 C6 -178.78(8) 1_555 1_555 1_555 1_555 yes C1 C3 C5 H5 3.04 1_555 1_555 1_555 1_555 yes C4 C3 C5 C6 0.96(5) 1_555 1_555 1_555 1_555 yes C5 C3 C4 C7 -2.11(5) 1_555 1_555 1_555 1_555 yes C5 C3 C4 H4 179.34 1_555 1_555 1_555 1_555 yes C4 C3 C5 H5 -177.23 1_555 1_555 1_555 1_555 yes C3 C4 C7 C8 1.21(5) 1_555 1_555 1_555 1_555 yes C3 C4 C7 H7 -178.61 1_555 1_555 1_555 1_555 yes H4 C4 C7 C8 179.76 1_555 1_555 1_555 1_555 yes H4 C4 C7 H7 -0.06 1_555 1_555 1_555 1_555 yes C3 C5 C6 C8 1.04(5) 1_555 1_555 1_555 1_555 yes C3 C5 C6 H6 -178.84 1_555 1_555 1_555 1_555 yes H5 C5 C6 C8 179.21 1_555 1_555 1_555 1_555 yes H5 C5 C6 H6 -0.67 1_555 1_555 1_555 1_555 yes C5 C6 C8 N2 178.38(7) 1_555 1_555 1_555 1_555 yes C5 C6 C8 C7 -1.98(5) 1_555 1_555 1_555 1_555 yes H6 C6 C8 N2 -1.74 1_555 1_555 1_555 1_555 yes H6 C6 C8 C7 177.90 1_555 1_555 1_555 1_555 yes C4 C7 C8 N2 -179.50(8) 1_555 1_555 1_555 1_555 yes C4 C7 C8 C6 0.86(5) 1_555 1_555 1_555 1_555 yes H7 C7 C8 N2 0.32 1_555 1_555 1_555 1_555 yes H7 C7 C8 C6 -179.32 1_555 1_555 1_555 1_555 yes N1A C1A C2A C9A 105.76(5) 1_555 1_555 1_555 1_555 yes N1A C1A C2A C11A -106.10(5) 1_555 1_555 1_555 1_555 yes N1A C1A C3A C4A 21.53(5) 1_555 1_555 1_555 1_555 yes N1A C1A C3A C5A -157.45(7) 1_555 1_555 1_555 1_555 yes C3A C1A C2A N1A -105.85(5) 1_555 1_555 1_555 1_555 yes C2A C1A C3A C4A 89.55(6) 1_555 1_555 1_555 1_555 yes C2A C1A C3A C5A -89.43(6) 1_555 1_555 1_555 1_555 yes C3A C1A C2A C9A -0.09(4) 1_555 1_555 1_555 1_555 yes C3A C1A C2A C11A 148.05(7) 1_555 1_555 1_555 1_555 yes H1A C1A C2A N1A 108.88 1_555 1_555 1_555 1_555 yes H1A C1A C2A C9A -145.36 1_555 1_555 1_555 1_555 yes H1A C1A C2A C11A 2.78 1_555 1_555 1_555 1_555 yes H1A C1A C3A C4A -126.00 1_555 1_555 1_555 1_555 yes H1A C1A C3A C5A 55.02 1_555 1_555 1_555 1_555 yes N1A C2A C9A O3A -37.33(5) 1_555 1_555 1_555 1_555 yes N1A C2A C9A O4A 140.48(6) 1_555 1_555 1_555 1_555 yes N1A C2A C11A O5A -27.62(5) 1_555 1_555 1_555 1_555 yes N1A C2A C11A O6A 152.39(6) 1_555 1_555 1_555 1_555 yes C1A C2A C9A O3A -104.21(7) 1_555 1_555 1_555 1_555 yes C1A C2A C9A O4A 73.60(5) 1_555 1_555 1_555 1_555 yes C1A C2A C11A O5A 38.90(5) 1_555 1_555 1_555 1_555 yes C1A C2A C11A O6A -141.09(6) 1_555 1_555 1_555 1_555 yes C11A C2A C9A O3A 108.21(7) 1_555 1_555 1_555 1_555 yes C11A C2A C9A O4A -73.98(5) 1_555 1_555 1_555 1_555 yes C9A C2A C11A O5A -173.20(7) 1_555 1_555 1_555 1_555 yes C9A C2A C11A O6A 6.81(4) 1_555 1_555 1_555 1_555 yes C1A C3A C4A C7A -179.89(8) 1_555 1_555 1_555 1_555 yes C1A C3A C4A H4A 0.03 1_555 1_555 1_555 1_555 yes C1A C3A C5A C6A 178.26(8) 1_555 1_555 1_555 1_555 yes C1A C3A C5A H5A 0.09 1_555 1_555 1_555 1_555 yes C4A C3A C5A C6A -0.72(5) 1_555 1_555 1_555 1_555 yes C5A C3A C4A C7A -0.91(5) 1_555 1_555 1_555 1_555 yes C5A C3A C4A H4A 179.00 1_555 1_555 1_555 1_555 yes C4A C3A C5A H5A -178.89 1_555 1_555 1_555 1_555 yes C3A C4A C7A C8A 1.58(5) 1_555 1_555 1_555 1_555 yes C3A C4A C7A H7A -179.69 1_555 1_555 1_555 1_555 yes H4A C4A C7A C8A -178.33 1_555 1_555 1_555 1_555 yes H4A C4A C7A H7A 0.40 1_555 1_555 1_555 1_555 yes C3A C5A C6A C8A 1.61(5) 1_555 1_555 1_555 1_555 yes C3A C5A C6A H6A -177.69 1_555 1_555 1_555 1_555 yes H5A C5A C6A C8A 179.86 1_555 1_555 1_555 1_555 yes H5A C5A C6A H6A 0.57 1_555 1_555 1_555 1_555 yes C5A C6A C8A N2A -179.47(8) 1_555 1_555 1_555 1_555 yes C5A C6A C8A C7A -0.92(5) 1_555 1_555 1_555 1_555 yes H6A C6A C8A N2A -0.16 1_555 1_555 1_555 1_555 yes H6A C6A C8A C7A 178.39 1_555 1_555 1_555 1_555 yes C4A C7A C8A N2A 177.89(8) 1_555 1_555 1_555 1_555 yes C4A C7A C8A C6A -0.67(5) 1_555 1_555 1_555 1_555 yes H7A C7A C8A N2A -0.84 1_555 1_555 1_555 1_555 yes H7A C7A C8A C6A -179.39 1_555 1_555 1_555 1_555 yes data_Oxiran _publ_contact_author ; Prof. Dr. Peter Luger Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany ; _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_author_fax '0049-30-838-53464' _publ_contact_author_phone '0049-30-838-53411' _publ_requested_journal 'Organo and Biomolecular Chemistry' _publ_section_title ; A Comparative Study on the Experimentally Derived Electron Densities of three Protease Inhibitor Model Compounds ; loop_ _publ_author_name ; Grabowsky, Simon ; ; Pfeuffer, Thomas ; ; Morgenroth, Wolfgang ; ; Paulmann, Carsten ; ; Schirmeister, Tanja ; ; Luger, Peter ; _publ_author_address ; Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany and Universit\"at W\"urzburg Institut f\"ur Pharmazie und Lebensmittelchemie Am Hubland 97074 W/"urzburg Germany ; _chemical_name_common 'acceptor-substituted oxirane' _chemical_formula_moiety 'C12 H11 N O7' _chemical_formula_sum 'C12 H11 N O7' _chemical_formula_weight 281.22 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 7.746(1) _cell_length_b 8.080(1) _cell_length_c 11.835(1) _cell_angle_alpha 86.198(1) _cell_angle_beta 74.105(1) _cell_angle_gamma 60.673(1) _cell_volume 619.07(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2938 _cell_measurement_theta_min 14.48 _cell_measurement_theta_max 41.81 _exptl_crystal_description block _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type 'none' _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.56000 _diffrn_radiation_type 'synchrotron' _diffrn_measurement_device_type 'MarCCD 165 detector' _diffrn_measurement_method 'phi scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 126224 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 41.81 _diffrn_measured_fraction_theta_max 0.842 _diffrn_reflns_theta_full 20.49 _diffrn_measured_fraction_theta_full 0.953 _reflns_number_total 14724 _reflns_number_gt 8523 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_cell_refinement 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_data_reduction 'SORTAV Blessing, R. J. Appl. Cryst. 22, 396 (1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_number_reflns 8523 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.032 _refine_ls_R_factor_all 0.058 _refine_ls_R_Fsqd_factor 0.048 _refine_ls_wR_factor_ref 0.044 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.189 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.046 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O1 0.22981(8) 1.24582(9) 0.54056(7) 1 2 0.032 O2 0.23779(9) 1.06887(10) 0.68593(6) 1 2 0.034 O3 0.62500(7) 0.61634(6) 0.06896(4) 1 2 0.021 O4 0.76238(6) 0.41570(6) 0.20079(4) 1 2 0.019 O5 0.40368(7) 0.17999(6) 0.16857(3) 1 2 0.020 O6 0.71006(6) 0.15321(6) 0.06819(4) 1 2 0.020 O7 0.25847(6) 0.58310(6) 0.17514(4) 1 2 0.020 N2 0.24031(6) 1.09956(8) 0.58320(5) 1 2 0.022 C1 0.29256(7) 0.53500(7) 0.28894(5) 1 2 0.018 C2 0.46062(6) 0.44372(6) 0.17803(4) 1 2 0.016 C3 0.27982(6) 0.68375(6) 0.36358(4) 1 2 0.017 C4 0.28329(7) 0.84596(7) 0.31613(4) 1 2 0.020 C5 0.26310(7) 0.65969(6) 0.48362(4) 1 2 0.019 C6 0.25188(7) 0.79519(7) 0.55610(4) 1 2 0.019 C7 0.27201(7) 0.98243(6) 0.38789(4) 1 2 0.020 C8 0.25616(6) 0.95414(6) 0.50648(4) 1 2 0.018 C9 0.62413(6) 0.50329(6) 0.14053(4) 1 2 0.015 C10 0.92505(7) 0.46398(7) 0.17931(4) 1 2 0.022 C11 0.52012(6) 0.24361(6) 0.13845(4) 1 2 0.016 C12 0.77604(8) -0.03540(8) 0.02078(6) 1 2 0.028 H1 0.22626 0.449498 0.337738 1 2 0.038(5) H4 0.294397 0.871287 0.2241 1 2 0.038(4) H5 0.258072 0.536142 0.521933 1 2 0.038(4) H6 0.238241 0.782775 0.649394 1 2 0.049(4) H7 0.279309 1.107411 0.354169 1 2 0.048(4) H10A 0.85852 0.611618 0.204154 1 2 0.054(5) H10B 1.003724 0.441301 0.087689 1 2 0.046(4) H10C 1.016598 0.384206 0.236629 1 2 0.052(4) H12A 0.929129 -0.09891 -0.03617 1 2 0.105(7) H12B 0.781566 -0.13309 0.086689 1 2 0.126(9) H12C 0.667988 -0.012075 -0.026423 1 2 0.062(5) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0480(3) 0.02512(19) 0.0328(3) -0.0252(2) -0.01017(19) -0.00168(18) O2 0.0537(4) 0.0332(2) 0.0238(2) -0.0258(2) -0.01400(19) -0.00246(19) O3 0.02317(14) 0.02303(16) 0.02096(13) -0.01370(13) -0.00704(13) 0.00504(14) O4 0.01789(11) 0.02102(14) 0.02211(13) -0.01237(11) -0.00779(11) 0.00325(12) O5 0.02022(13) 0.02079(15) 0.02149(13) -0.01350(12) -0.00336(12) -0.00209(11) O6 0.01546(11) 0.01864(13) 0.02617(15) -0.00869(10) -0.00214(11) -0.00776(12) O7 0.01540(10) 0.01947(14) 0.02346(14) -0.00711(10) -0.00634(14) -0.00356(12) N2 0.02298(18) 0.02103(17) 0.02359(18) -0.01276(13) -0.00519(12) -0.00446(15) C1 0.01615(13) 0.01830(17) 0.02013(16) -0.00940(13) -0.00212(13) -0.00449(13) C2 0.01429(12) 0.01583(15) 0.01802(14) -0.00762(11) -0.00351(12) -0.00289(12) C3 0.01655(13) 0.01604(14) 0.01798(14) -0.00843(11) -0.00215(10) -0.00310(12) C4 0.02384(16) 0.01747(16) 0.01724(15) -0.01054(13) -0.00337(12) -0.00161(12) C5 0.02173(15) 0.01742(15) 0.01871(15) -0.01114(13) -0.00311(12) -0.00131(12) C6 0.02318(16) 0.01860(16) 0.01765(15) -0.01155(13) -0.00487(12) -0.00076(12) C7 0.02397(16) 0.01668(16) 0.01888(15) -0.01130(13) -0.00356(12) -0.00095(12) C8 0.01779(14) 0.01685(14) 0.01875(14) -0.00942(12) -0.00352(11) -0.00225(12) C9 0.01573(11) 0.01576(13) 0.01608(12) -0.00860(10) -0.00387(10) -0.00093(10) C10 0.01901(14) 0.02543(19) 0.02693(18) -0.01407(14) -0.00668(13) -0.00028(14) C11 0.01558(12) 0.01654(14) 0.01792(13) -0.00909(11) -0.00374(11) -0.00252(11) C12 0.02237(16) 0.02305(19) 0.0380(3) -0.01047(14) -0.00291(17) -0.01363(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.2276(9) 1_555 1_555 yes O2 N2 1.2213(9) 1_555 1_555 yes O3 C9 1.2051(7) 1_555 1_555 yes O4 C9 1.3287(6) 1_555 1_555 yes O4 C10 1.4482(6) 1_555 1_555 yes O5 C11 1.2076(6) 1_555 1_555 yes O6 C11 1.3219(6) 1_555 1_555 yes O6 C12 1.4463(6) 1_555 1_555 yes O7 C1 1.4351(8) 1_555 1_555 yes O7 C2 1.4207(7) 1_555 1_555 yes N2 C8 1.4695(6) 1_555 1_555 yes C1 C2 1.4878(6) 1_555 1_555 yes C1 C3 1.4871(6) 1_555 1_555 yes C1 H1 1.0985 1_555 1_555 yes C2 C9 1.5145(6) 1_555 1_555 yes C2 C11 1.5160(5) 1_555 1_555 yes C3 C4 1.4008(6) 1_555 1_555 yes C3 C5 1.4001(6) 1_555 1_555 yes C4 C7 1.3907(6) 1_555 1_555 yes C4 H4 1.0826 1_555 1_555 yes C5 C6 1.3902(6) 1_555 1_555 yes C5 H5 1.0826 1_555 1_555 yes C6 C8 1.3880(7) 1_555 1_555 yes C6 H6 1.0826 1_555 1_555 yes C7 C8 1.3884(7) 1_555 1_555 yes C7 H7 1.0828 1_555 1_555 yes C10 H10A 1.0660 1_555 1_555 yes C10 H10B 1.0657 1_555 1_555 yes C10 H10C 1.0660 1_555 1_555 yes C12 H12A 1.0657 1_555 1_555 yes C12 H12B 1.0663 1_555 1_555 yes C12 H12C 1.0657 1_555 1_555 yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O4 C10 116.61(4) 1_555 1_555 1_555 yes C11 O6 C12 115.38(4) 1_555 1_555 1_555 yes C1 O7 C2 62.79(3) 1_555 1_555 1_555 yes O1 N2 O2 123.49(7) 1_555 1_555 1_555 yes O1 N2 C8 118.15(6) 1_555 1_555 1_555 yes O2 N2 C8 118.36(6) 1_555 1_555 1_555 yes O7 C1 C2 58.13(3) 1_555 1_555 1_555 yes O7 C1 C3 117.42(4) 1_555 1_555 1_555 yes O7 C1 H1 116.15 1_555 1_555 1_555 yes C2 C1 C3 121.92(4) 1_555 1_555 1_555 yes C2 C1 H1 117.30 1_555 1_555 1_555 yes C3 C1 H1 114.32 1_555 1_555 1_555 yes O7 C2 C1 59.08(3) 1_555 1_555 1_555 yes O7 C2 C9 116.27(4) 1_555 1_555 1_555 yes O7 C2 C11 113.73(3) 1_555 1_555 1_555 yes C1 C2 C9 118.99(3) 1_555 1_555 1_555 yes C1 C2 C11 117.48(4) 1_555 1_555 1_555 yes C9 C2 C11 117.69(3) 1_555 1_555 1_555 yes C1 C3 C4 121.32(4) 1_555 1_555 1_555 yes C1 C3 C5 118.68(4) 1_555 1_555 1_555 yes C4 C3 C5 120.00(4) 1_555 1_555 1_555 yes C3 C4 C7 120.10(5) 1_555 1_555 1_555 yes C3 C4 H4 122.58 1_555 1_555 1_555 yes C7 C4 H4 117.33 1_555 1_555 1_555 yes C3 C5 C6 120.36(4) 1_555 1_555 1_555 yes C3 C5 H5 120.94 1_555 1_555 1_555 yes C6 C5 H5 118.70 1_555 1_555 1_555 yes C5 C6 C8 118.30(5) 1_555 1_555 1_555 yes C5 C6 H6 122.90 1_555 1_555 1_555 yes C8 C6 H6 118.80 1_555 1_555 1_555 yes C4 C7 C8 118.51(4) 1_555 1_555 1_555 yes C4 C7 H7 122.42 1_555 1_555 1_555 yes C8 C7 H7 119.04 1_555 1_555 1_555 yes N2 C8 C6 118.50(4) 1_555 1_555 1_555 yes N2 C8 C7 118.77(4) 1_555 1_555 1_555 yes C6 C8 C7 122.73(4) 1_555 1_555 1_555 yes O3 C9 O4 125.54(4) 1_555 1_555 1_555 yes O3 C9 C2 124.89(4) 1_555 1_555 1_555 yes O4 C9 C2 109.55(4) 1_555 1_555 1_555 yes O4 C10 H10A 109.05 1_555 1_555 1_555 yes O4 C10 H10B 110.24 1_555 1_555 1_555 yes O4 C10 H10C 105.80 1_555 1_555 1_555 yes H10A C10 H10B 107.22 1_555 1_555 1_555 yes H10A C10 H10C 108.22 1_555 1_555 1_555 yes H10B C10 H10C 116.15 1_555 1_555 1_555 yes O5 C11 O6 125.88(4) 1_555 1_555 1_555 yes O5 C11 C2 122.55(4) 1_555 1_555 1_555 yes O6 C11 C2 111.57(4) 1_555 1_555 1_555 yes O6 C12 H12A 111.44 1_555 1_555 1_555 yes O6 C12 H12B 113.33 1_555 1_555 1_555 yes O6 C12 H12C 103.90 1_555 1_555 1_555 yes H12A C12 H12B 104.52 1_555 1_555 1_555 yes H12A C12 H12C 111.12 1_555 1_555 1_555 yes H12B C12 H12C 112.73 1_555 1_555 1_555 yes 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 C10 O4 C9 O3 1.14(5) 1_555 1_555 1_555 1_555 yes C10 O4 C9 C2 -177.23(5) 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10A 62.06 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10B -55.40 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10C 178.27 1_555 1_555 1_555 1_555 yes C12 O6 C11 O5 2.81(5) 1_555 1_555 1_555 1_555 yes C12 O6 C11 C2 -176.71(5) 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12A 178.96 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12B -63.48 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12C 59.22 1_555 1_555 1_555 1_555 yes C2 O7 C1 C3 112.26(5) 1_555 1_555 1_555 1_555 yes C1 O7 C2 C9 -109.54(4) 1_555 1_555 1_555 1_555 yes C1 O7 C2 C11 108.92(4) 1_555 1_555 1_555 1_555 yes C2 O7 C1 H1 -107.24 1_555 1_555 1_555 1_555 yes O1 N2 C8 C6 -175.04(7) 1_555 1_555 1_555 1_555 yes O1 N2 C8 C7 4.11(5) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C6 4.79(5) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C7 -176.05(7) 1_555 1_555 1_555 1_555 yes O7 C1 C2 C9 104.95(4) 1_555 1_555 1_555 1_555 yes O7 C1 C2 C11 -102.55(4) 1_555 1_555 1_555 1_555 yes O7 C1 C3 C4 -14.72(4) 1_555 1_555 1_555 1_555 yes O7 C1 C3 C5 164.97(6) 1_555 1_555 1_555 1_555 yes C3 C1 C2 O7 -104.57(5) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C4 53.09(5) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C5 -127.21(6) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C9 0.38(4) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C11 152.88(6) 1_555 1_555 1_555 1_555 yes H1 C1 C2 O7 105.26 1_555 1_555 1_555 1_555 yes H1 C1 C2 C9 -149.79 1_555 1_555 1_555 1_555 yes H1 C1 C2 C11 2.71 1_555 1_555 1_555 1_555 yes H1 C1 C3 C4 -155.92 1_555 1_555 1_555 1_555 yes H1 C1 C3 C5 23.77 1_555 1_555 1_555 1_555 yes O7 C2 C9 O3 -30.81(5) 1_555 1_555 1_555 1_555 yes O7 C2 C9 O4 147.57(5) 1_555 1_555 1_555 1_555 yes O7 C2 C11 O5 -42.70(5) 1_555 1_555 1_555 1_555 yes O7 C2 C11 O6 136.83(5) 1_555 1_555 1_555 1_555 yes C1 C2 C9 O3 -98.37(6) 1_555 1_555 1_555 1_555 yes C1 C2 C9 O4 80.01(5) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O5 23.47(4) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O6 -157.00(5) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O3 109.18(6) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O4 -72.44(4) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O5 176.33(6) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O6 -4.13(4) 1_555 1_555 1_555 1_555 yes C1 C3 C4 C7 -179.73(7) 1_555 1_555 1_555 1_555 yes C1 C3 C4 H4 0.35 1_555 1_555 1_555 1_555 yes C1 C3 C5 C6 179.68(6) 1_555 1_555 1_555 1_555 yes C1 C3 C5 H5 -0.55 1_555 1_555 1_555 1_555 yes C4 C3 C5 C6 -0.63(4) 1_555 1_555 1_555 1_555 yes C5 C3 C4 C7 0.58(4) 1_555 1_555 1_555 1_555 yes C5 C3 C4 H4 -179.34 1_555 1_555 1_555 1_555 yes C4 C3 C5 H5 179.14 1_555 1_555 1_555 1_555 yes C3 C4 C7 C8 -0.38(4) 1_555 1_555 1_555 1_555 yes C3 C4 C7 H7 177.92 1_555 1_555 1_555 1_555 yes H4 C4 C7 C8 179.54 1_555 1_555 1_555 1_555 yes H4 C4 C7 H7 -2.15 1_555 1_555 1_555 1_555 yes C3 C5 C6 C8 0.47(4) 1_555 1_555 1_555 1_555 yes C3 C5 C6 H6 179.75 1_555 1_555 1_555 1_555 yes H5 C5 C6 C8 -179.30 1_555 1_555 1_555 1_555 yes H5 C5 C6 H6 -0.03 1_555 1_555 1_555 1_555 yes C5 C6 C8 N2 178.84(6) 1_555 1_555 1_555 1_555 yes C5 C6 C8 C7 -0.28(4) 1_555 1_555 1_555 1_555 yes H6 C6 C8 N2 -0.47 1_555 1_555 1_555 1_555 yes H6 C6 C8 C7 -179.59 1_555 1_555 1_555 1_555 yes C4 C7 C8 N2 -178.88(6) 1_555 1_555 1_555 1_555 yes C4 C7 C8 C6 0.24(4) 1_555 1_555 1_555 1_555 yes H7 C7 C8 N2 2.76 1_555 1_555 1_555 1_555 yes H7 C7 C8 C6 -178.12 1_555 1_555 1_555 1_555 yes data_Olefin _publ_contact_author ; Prof. Dr. Peter Luger Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany ; _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_author_fax '0049-30-838-53464' _publ_contact_author_phone '0049-30-838-53411' _publ_requested_journal 'Organo and Biomolecular Chemistry' _publ_section_title ; A Comparative Study on the Experimentally Derived Electron Densities of three Protease Inhibitor Model Compounds ; loop_ _publ_author_name ; Grabowsky, Simon ; ; Pfeuffer, Thomas ; ; Morgenroth, Wolfgang ; ; Paulmann, Carsten ; ; Schirmeister, Tanja ; ; Luger, Peter ; _publ_author_address ; Freie Universit\"at Berlin Institut f\"ur Chemie und Biochemie Kristallographie Fabeckstr. 36a 14195 Berlin Germany and Universit\"at W\"urzburg Institut f\"ur Pharmazie und Lebensmittelchemie Am Hubland 97074 W/"urzburg Germany ; _chemical_name_common 'acceptor-substituted olefin' _chemical_formula_moiety 'C12 H11 N O6' _chemical_formula_sum 'C12 H11 N O6' _chemical_formula_weight 265.22 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 7.769(2) _cell_length_b 7.865(1) _cell_length_c 10.811(1) _cell_angle_alpha 87.61(2) _cell_angle_beta 85.41(4) _cell_angle_gamma 62.43(1) _cell_volume 583.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 9 _cell_measurement_reflns_used 3350 _cell_measurement_theta_min 10.12 _cell_measurement_theta_max 31.61 _exptl_crystal_description block _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'none' _diffrn_ambient_temperature 9 _diffrn_radiation_wavelength 0.51660 _diffrn_radiation_type 'synchrotron' _diffrn_measurement_device_type 'MarCCD 165 detector' _diffrn_measurement_method 'phi scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 104810 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 31.61 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 20.15 _diffrn_measured_fraction_theta_full 0.955 _reflns_number_total 9203 _reflns_number_gt 7557 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_cell_refinement 'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)' _computing_data_reduction 'SORTAV Blessing, R. J. Appl. Cryst. 22, 396 (1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_number_reflns 7557 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.027 _refine_ls_R_factor_all 0.034 _refine_ls_R_Fsqd_factor 0.049 _refine_ls_wR_factor_ref 0.033 _refine_ls_goodness_of_fit_ref 1.468 _refine_ls_shift/su_max 0.00242 _refine_diff_density_max 0.357 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.092 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O1 -0.52357(5) 0.71299(5) -0.18990(3) 1 2 0.010 O2 -0.41098(5) 0.48129(5) -0.32270(3) 1 2 0.010 O3 0.09381(5) 0.35765(5) 0.32816(3) 1 2 0.009 O4 -0.01277(5) 0.13505(5) 0.34696(3) 1 2 0.008 O5 0.56259(5) -0.18143(5) 0.17079(3) 1 2 0.009 O6 0.43757(5) -0.07003(4) 0.36257(3) 1 2 0.008 N2 -0.40670(5) 0.55028(5) -0.22390(3) 1 2 0.007 C1 0.21316(6) 0.08710(5) 0.07658(3) 1 2 0.007 C2 0.24200(5) 0.08068(5) 0.19811(3) 1 2 0.006 C3 0.04465(5) 0.21090(5) 0.00766(3) 1 2 0.006 C4 -0.11545(5) 0.37841(5) 0.05375(3) 1 2 0.007 C5 0.04981(5) 0.15634(5) -0.11519(3) 1 2 0.007 C6 -0.09913(5) 0.26493(5) -0.19085(3) 1 2 0.007 C7 -0.26466(5) 0.49004(5) -0.02163(3) 1 2 0.007 C8 -0.25338(5) 0.43115(5) -0.14257(3) 1 2 0.006 C9 0.10083(5) 0.20883(5) 0.29682(3) 1 2 0.006 C10 -0.15082(5) 0.24285(5) 0.44727(3) 1 2 0.010 C11 0.43120(5) -0.07037(5) 0.23938(3) 1 2 0.006 C12 0.61700(6) -0.21158(5) 0.41080(3) 1 2 0.011 H1 0.333169 -0.018858 0.02081 1 2 0.019(2) H4 -0.123313 0.429791 0.146466 1 2 0.022(2) H5 0.172615 0.026707 -0.150996 1 2 0.024(2) H6 -0.095286 0.221429 -0.285191 1 2 0.021(2) H7 -0.38509 0.623526 0.011299 1 2 0.027(2) H10A -0.279787 0.348005 0.408334 1 2 0.036(2) H10B -0.08693 0.307525 0.50022 1 2 0.040(2) H10C -0.179578 0.139642 0.499423 1 2 0.035(2) H12A 0.585694 -0.213512 0.50852 1 2 0.038(2) H12B 0.656864 -0.347797 0.371245 1 2 0.044(3) H12C 0.725706 -0.16585 0.390297 1 2 0.044(3) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.00897(13) 0.00678(11) 0.01066(12) -0.00092(11) -0.00164(9) -0.00061(9) O2 0.01019(13) 0.01022(12) 0.00817(11) -0.00327(11) -0.00311(9) -0.00103(9) O3 0.01177(13) 0.00727(10) 0.00983(11) -0.00536(10) 0.00189(10) -0.00236(9) O4 0.00786(11) 0.00751(10) 0.00863(10) -0.00415(9) 0.00205(9) -0.00085(8) O5 0.00706(13) 0.00924(10) 0.00753(12) -0.00067(11) 0.00024(9) -0.00173(9) O6 0.00757(12) 0.00778(10) 0.00565(11) -0.00185(10) -0.00117(8) -0.00011(8) N2 0.00647(12) 0.00596(11) 0.00712(12) -0.00218(10) -0.00104(9) 0.00009(10) C1 0.00675(15) 0.00696(12) 0.00579(13) -0.00233(11) -0.00094(9) -0.00000(10) C2 0.00611(14) 0.00614(12) 0.00573(13) -0.00225(11) -0.00061(9) 0.00003(9) C3 0.00621(13) 0.00624(10) 0.00585(11) -0.00229(10) -0.00073(8) -0.00011(9) C4 0.00729(13) 0.00720(11) 0.00617(12) -0.00204(10) -0.00095(8) -0.00071(9) C5 0.00690(13) 0.00643(11) 0.00622(12) -0.00177(10) -0.00066(8) -0.00058(8) C6 0.00739(13) 0.00652(11) 0.00631(12) -0.00202(10) -0.00115(8) -0.00055(9) C7 0.00691(13) 0.00685(11) 0.00666(12) -0.00200(10) -0.00087(8) -0.00078(9) C8 0.00620(13) 0.00606(10) 0.00619(11) -0.00229(10) -0.00076(9) -0.00014(9) C9 0.00701(13) 0.00601(11) 0.00620(11) -0.00321(10) 0.00022(8) -0.00033(8) C10 0.00879(14) 0.01035(12) 0.00918(12) -0.00343(10) 0.00201(9) 0.00025(9) C11 0.00594(13) 0.00637(11) 0.00575(12) -0.00205(10) -0.00014(8) -0.00060(8) C12 0.01035(15) 0.00974(12) 0.00957(13) -0.00248(11) -0.00347(9) 0.00073(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.2278(5) 1_555 1_555 yes O2 N2 1.2277(5) 1_555 1_555 yes O3 C9 1.2078(5) 1_555 1_555 yes O4 C9 1.3345(5) 1_555 1_555 yes O4 C10 1.4470(5) 1_555 1_555 yes O5 C11 1.2093(5) 1_555 1_555 yes O6 C11 1.3368(5) 1_555 1_555 yes O6 C12 1.4442(5) 1_555 1_555 yes N2 C8 1.4613(5) 1_555 1_555 yes C1 C2 1.3454(5) 1_555 1_555 yes C1 C3 1.4604(5) 1_555 1_555 yes C1 H1 1.0770 1_555 1_555 yes C2 C9 1.4955(5) 1_555 1_555 yes C2 C11 1.4883(5) 1_555 1_555 yes C3 C4 1.4034(5) 1_555 1_555 yes C3 C5 1.4045(5) 1_555 1_555 yes C4 C7 1.3885(5) 1_555 1_555 yes C4 H4 1.0830 1_555 1_555 yes C5 C6 1.3841(5) 1_555 1_555 yes C5 H5 1.0830 1_555 1_555 yes C6 C8 1.3871(5) 1_555 1_555 yes C6 H6 1.0830 1_555 1_555 yes C7 C8 1.3879(5) 1_555 1_555 yes C7 H7 1.0830 1_555 1_555 yes C10 H10A 1.0660 1_555 1_555 yes C10 H10B 1.0660 1_555 1_555 yes C10 H10C 1.0660 1_555 1_555 yes C12 H12A 1.0660 1_555 1_555 yes C12 H12B 1.0660 1_555 1_555 yes C12 H12C 1.0660 1_555 1_555 yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O4 C10 116.25(3) 1_555 1_555 1_555 yes C11 O6 C12 115.32(3) 1_555 1_555 1_555 yes O1 N2 O2 123.74(5) 1_555 1_555 1_555 yes O1 N2 C8 118.43(4) 1_555 1_555 1_555 yes O2 N2 C8 117.83(4) 1_555 1_555 1_555 yes C2 C1 C3 130.89(3) 1_555 1_555 1_555 yes C2 C1 H1 114.75 1_555 1_555 1_555 yes C3 C1 H1 114.35 1_555 1_555 1_555 yes C1 C2 C9 126.34(3) 1_555 1_555 1_555 yes C1 C2 C11 117.18(3) 1_555 1_555 1_555 yes C9 C2 C11 116.47(3) 1_555 1_555 1_555 yes C1 C3 C4 125.22(3) 1_555 1_555 1_555 yes C1 C3 C5 115.83(3) 1_555 1_555 1_555 yes C4 C3 C5 118.93(4) 1_555 1_555 1_555 yes C3 C4 C7 120.48(3) 1_555 1_555 1_555 yes C3 C4 H4 121.72 1_555 1_555 1_555 yes C7 C4 H4 117.70 1_555 1_555 1_555 yes C3 C5 C6 121.19(3) 1_555 1_555 1_555 yes C3 C5 H5 119.20 1_555 1_555 1_555 yes C6 C5 H5 119.60 1_555 1_555 1_555 yes C5 C6 C8 118.17(3) 1_555 1_555 1_555 yes C5 C6 H6 120.93 1_555 1_555 1_555 yes C8 C6 H6 120.90 1_555 1_555 1_555 yes C4 C7 C8 118.68(3) 1_555 1_555 1_555 yes C4 C7 H7 121.16 1_555 1_555 1_555 yes C8 C7 H7 120.12 1_555 1_555 1_555 yes N2 C8 C6 118.26(3) 1_555 1_555 1_555 yes N2 C8 C7 119.18(3) 1_555 1_555 1_555 yes C6 C8 C7 122.53(4) 1_555 1_555 1_555 yes O3 C9 O4 124.76(4) 1_555 1_555 1_555 yes O3 C9 C2 124.12(3) 1_555 1_555 1_555 yes O4 C9 C2 111.10(3) 1_555 1_555 1_555 yes O4 C10 H10A 108.42 1_555 1_555 1_555 yes O4 C10 H10B 108.88 1_555 1_555 1_555 yes O4 C10 H10C 104.79 1_555 1_555 1_555 yes H10A C10 H10B 111.43 1_555 1_555 1_555 yes H10A C10 H10C 110.50 1_555 1_555 1_555 yes H10B C10 H10C 112.53 1_555 1_555 1_555 yes O5 C11 O6 123.87(4) 1_555 1_555 1_555 yes O5 C11 C2 124.57(4) 1_555 1_555 1_555 yes O6 C11 C2 111.55(3) 1_555 1_555 1_555 yes O6 C12 H12A 105.16 1_555 1_555 1_555 yes O6 C12 H12B 109.44 1_555 1_555 1_555 yes O6 C12 H12C 108.43 1_555 1_555 1_555 yes H12A C12 H12B 110.87 1_555 1_555 1_555 yes H12A C12 H12C 110.60 1_555 1_555 1_555 yes H12B C12 H12C 112.08 1_555 1_555 1_555 yes 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 C10 O4 C9 O3 -1.02(4) 1_555 1_555 1_555 1_555 yes C10 O4 C9 C2 177.69(4) 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10A 86.39 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10B -35.00 1_555 1_555 1_555 1_555 yes C9 O4 C10 H10C -155.60 1_555 1_555 1_555 1_555 yes C12 O6 C11 O5 1.17(4) 1_555 1_555 1_555 1_555 yes C12 O6 C11 C2 -179.59(4) 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12A -167.18 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12B -48.04 1_555 1_555 1_555 1_555 yes C11 O6 C12 H12C 74.49 1_555 1_555 1_555 1_555 yes O1 N2 C8 C6 -166.84(5) 1_555 1_555 1_555 1_555 yes O1 N2 C8 C7 11.66(4) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C6 13.15(4) 1_555 1_555 1_555 1_555 yes O2 N2 C8 C7 -168.34(5) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C4 12.77(4) 1_555 1_555 1_555 1_555 yes C2 C1 C3 C5 -168.75(6) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C9 -1.17(4) 1_555 1_555 1_555 1_555 yes C3 C1 C2 C11 177.74(6) 1_555 1_555 1_555 1_555 yes H1 C1 C2 C9 -179.60 1_555 1_555 1_555 1_555 yes H1 C1 C2 C11 -0.70 1_555 1_555 1_555 1_555 yes H1 C1 C3 C4 -168.79 1_555 1_555 1_555 1_555 yes H1 C1 C3 C5 9.69 1_555 1_555 1_555 1_555 yes C1 C2 C9 O3 -91.06(5) 1_555 1_555 1_555 1_555 yes C1 C2 C9 O4 90.22(5) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O5 3.23(4) 1_555 1_555 1_555 1_555 yes C1 C2 C11 O6 -176.00(5) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O3 90.03(5) 1_555 1_555 1_555 1_555 yes C11 C2 C9 O4 -88.69(4) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O5 -177.76(5) 1_555 1_555 1_555 1_555 yes C9 C2 C11 O6 3.01(3) 1_555 1_555 1_555 1_555 yes C1 C3 C4 C7 177.36(6) 1_555 1_555 1_555 1_555 yes C1 C3 C4 H4 1.10 1_555 1_555 1_555 1_555 yes C1 C3 C5 C6 -178.34(5) 1_555 1_555 1_555 1_555 yes C1 C3 C5 H5 1.80 1_555 1_555 1_555 1_555 yes C4 C3 C5 C6 0.24(3) 1_555 1_555 1_555 1_555 yes C5 C3 C4 C7 -1.08(3) 1_555 1_555 1_555 1_555 yes C5 C3 C4 H4 -177.33 1_555 1_555 1_555 1_555 yes C4 C3 C5 H5 -179.62 1_555 1_555 1_555 1_555 yes C3 C4 C7 C8 0.87(3) 1_555 1_555 1_555 1_555 yes C3 C4 C7 H7 -176.69 1_555 1_555 1_555 1_555 yes H4 C4 C7 C8 177.28 1_555 1_555 1_555 1_555 yes H4 C4 C7 H7 -0.28 1_555 1_555 1_555 1_555 yes C3 C5 C6 C8 0.77(3) 1_555 1_555 1_555 1_555 yes C3 C5 C6 H6 -179.31 1_555 1_555 1_555 1_555 yes H5 C5 C6 C8 -179.37 1_555 1_555 1_555 1_555 yes H5 C5 C6 H6 0.55 1_555 1_555 1_555 1_555 yes C5 C6 C8 N2 177.45(5) 1_555 1_555 1_555 1_555 yes C5 C6 C8 C7 -1.00(3) 1_555 1_555 1_555 1_555 yes H6 C6 C8 N2 -2.47 1_555 1_555 1_555 1_555 yes H6 C6 C8 C7 179.08 1_555 1_555 1_555 1_555 yes C4 C7 C8 N2 -178.25(5) 1_555 1_555 1_555 1_555 yes C4 C7 C8 C6 0.18(3) 1_555 1_555 1_555 1_555 yes H7 C7 C8 N2 -0.67 1_555 1_555 1_555 1_555 yes H7 C7 C8 C6 177.77 1_555 1_555 1_555 1_555 yes