Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Ramtohul, Yeeman K.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Martin, Nathaniel I.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Silkin, Lara' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'James, Michael N. G.' ; Department of Biochemistry University of Alberta Edmonton Alberta T6G 2H7 Canada ; 'Vederas, John C.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_name 'Prof John C Vederas' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_email john.vederas@ualberta.ca _publ_contact_author_fax '1(780)4928231' _publ_contact_author_phone '1(780)4925475' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data which are being submitted in support of an upcoming communication to be published in Chemical Communications (manuscript B109095J). Please forward any questions concerning this CIF to John Vederas (John.Vederas@ualberta.ca). ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Pseudoxazolones, a New Class of Inhibitors for Cysteine Proteinases: Inhibition of Hepatitis A Virus and Human Rhinovirus 3C Proteinases ; data_jcv0107 _database_code_CSD 172532 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C10 H7 N O2' _chemical_formula_weight 173.17 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5390(6) _cell_length_b 7.2645(8) _cell_length_c 10.4291(11) _cell_angle_alpha 83.673(2) _cell_angle_beta 83.789(2) _cell_angle_gamma 80.624(2) _cell_volume 409.77(8) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1870 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2179 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.38 _reflns_number_total 1641 _reflns_number_gt 1365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0580P)^2^+0.0691P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1641 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.005 _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 0.09146(17) 0.27699(13) -0.17469(8) 0.0339(3) Uani 1 1 d . . . O2 O 0.2403(2) 0.30030(16) -0.38642(10) 0.0510(3) Uani 1 1 d . . . N N -0.3008(2) 0.42815(16) -0.19719(11) 0.0358(3) Uani 1 1 d . . . C1 C -0.1358(2) 0.33837(17) -0.11085(13) 0.0305(3) Uani 1 1 d . . . C2 C 0.0721(3) 0.3301(2) -0.30531(13) 0.0379(3) Uani 1 1 d . . . C3 C -0.1837(3) 0.4243(2) -0.31085(14) 0.0397(4) Uani 1 1 d . . . H3 H -0.2537 0.4759 -0.3886 0.048 Uiso 1 1 calc R . . C10 C -0.1891(2) 0.31654(17) 0.01801(13) 0.0311(3) Uani 1 1 d . . . H10 H -0.3525 0.3664 0.0475 0.037 Uiso 1 1 calc R . . C11 C -0.0364(2) 0.22861(17) 0.12002(13) 0.0292(3) Uani 1 1 d . . . C12 C 0.2040(3) 0.13248(18) 0.09854(13) 0.0328(3) Uani 1 1 d . . . H12 H 0.2772 0.1221 0.0124 0.039 Uiso 1 1 calc R . . C13 C 0.3345(3) 0.05310(19) 0.20162(14) 0.0373(3) Uani 1 1 d . . . H13 H 0.4960 -0.0127 0.1856 0.045 Uiso 1 1 calc R . . C14 C 0.2332(3) 0.0682(2) 0.32778(14) 0.0398(4) Uani 1 1 d . . . H14 H 0.3252 0.0145 0.3981 0.048 Uiso 1 1 calc R . . C15 C -0.0037(3) 0.1620(2) 0.35109(14) 0.0407(4) Uani 1 1 d . . . H15 H -0.0744 0.1725 0.4376 0.049 Uiso 1 1 calc R . . C16 C -0.1374(3) 0.24051(19) 0.24854(13) 0.0351(3) Uani 1 1 d . . . H16 H -0.3002 0.3034 0.2656 0.042 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 0.0319(5) 0.0383(5) 0.0291(5) -0.0024(4) -0.0024(4) 0.0013(4) O2 0.0484(7) 0.0672(7) 0.0323(6) -0.0073(5) 0.0017(5) 0.0045(5) N 0.0360(7) 0.0340(6) 0.0365(7) -0.0015(5) -0.0074(5) -0.0015(5) C1 0.0281(7) 0.0279(6) 0.0349(7) -0.0037(5) -0.0034(5) -0.0020(5) C2 0.0436(8) 0.0392(7) 0.0302(7) -0.0042(6) -0.0057(6) -0.0024(6) C3 0.0445(8) 0.0401(7) 0.0342(8) -0.0019(6) -0.0122(6) -0.0011(6) C10 0.0288(7) 0.0273(6) 0.0362(7) -0.0026(5) -0.0016(5) -0.0022(5) C11 0.0317(7) 0.0245(6) 0.0313(7) -0.0020(5) -0.0019(5) -0.0056(5) C12 0.0329(7) 0.0327(7) 0.0314(7) -0.0038(5) -0.0011(5) -0.0014(5) C13 0.0322(7) 0.0365(7) 0.0415(8) -0.0027(6) -0.0051(6) -0.0002(6) C14 0.0424(8) 0.0406(8) 0.0359(8) 0.0054(6) -0.0104(6) -0.0068(6) C15 0.0462(9) 0.0453(8) 0.0291(7) -0.0003(6) 0.0016(6) -0.0080(7) C16 0.0333(7) 0.0346(7) 0.0358(8) -0.0029(5) 0.0016(6) -0.0038(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 O1 C2 1.3851(17) . ? O1 C1 1.3884(16) . ? O2 C2 1.1976(17) . ? N C3 1.2890(19) . ? N C1 1.3879(18) . ? C1 C10 1.3419(19) . ? C2 C3 1.474(2) . ? C10 C11 1.4575(19) . ? C11 C16 1.4017(19) . ? C11 C12 1.4064(19) . ? C12 C13 1.381(2) . ? C13 C14 1.382(2) . ? C14 C15 1.386(2) . ? C15 C16 1.385(2) . ? 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 C2 O1 C1 106.55(11) . . ? C3 N C1 106.27(12) . . ? C10 C1 N 124.06(12) . . ? C10 C1 O1 124.56(12) . . ? N C1 O1 111.37(11) . . ? O2 C2 O1 122.88(14) . . ? O2 C2 C3 133.00(14) . . ? O1 C2 C3 104.12(12) . . ? N C3 C2 111.69(12) . . ? C1 C10 C11 130.33(13) . . ? C16 C11 C12 117.89(12) . . ? C16 C11 C10 117.44(12) . . ? C12 C11 C10 124.67(12) . . ? C13 C12 C11 120.52(12) . . ? C12 C13 C14 120.83(13) . . ? C13 C14 C15 119.58(13) . . ? C16 C15 C14 120.14(13) . . ? C15 C16 C11 121.04(13) . . ? 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 C3 N C1 C10 178.99(13) . . . . ? C3 N C1 O1 -0.10(15) . . . . ? C2 O1 C1 C10 -178.63(13) . . . . ? C2 O1 C1 N 0.45(14) . . . . ? C1 O1 C2 O2 178.55(14) . . . . ? C1 O1 C2 C3 -0.58(13) . . . . ? C1 N C3 C2 -0.29(16) . . . . ? O2 C2 C3 N -178.44(16) . . . . ? O1 C2 C3 N 0.56(16) . . . . ? N C1 C10 C11 -179.18(12) . . . . ? O1 C1 C10 C11 -0.2(2) . . . . ? C1 C10 C11 C16 174.81(13) . . . . ? C1 C10 C11 C12 -5.4(2) . . . . ? C16 C11 C12 C13 -0.06(19) . . . . ? C10 C11 C12 C13 -179.83(12) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C14 C15 C16 C11 -0.6(2) . . . . ? C12 C11 C16 C15 0.75(19) . . . . ? C10 C11 C16 C15 -179.46(12) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.259 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.040 #===END data_jcv9905 _database_code_CSD 172533 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C11 H9 N O2' _chemical_formula_weight 187.19 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0008(8) _cell_length_b 7.2370(11) _cell_length_c 10.9282(16) _cell_angle_alpha 95.403(2) _cell_angle_beta 101.029(3) _cell_angle_gamma 102.046(3) _cell_volume 451.10(11) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1595 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description fragment _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9736 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2409 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1827 _reflns_number_gt 1207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0513P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1827 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.002 _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 0.42236(18) 0.37848(17) 0.14193(12) 0.0394(4) Uani 1 1 d . . . O2 O 0.59862(19) 0.41231(18) 0.34789(12) 0.0469(4) Uani 1 1 d . . . N N 0.0480(2) 0.24823(19) 0.15780(14) 0.0329(4) Uani 1 1 d . . . C1 C 0.4248(3) 0.3641(2) 0.26597(18) 0.0356(4) Uani 1 1 d . . . C2 C 0.1782(3) 0.2811(2) 0.26944(17) 0.0327(4) Uani 1 1 d . . . C3 C 0.1907(3) 0.3070(2) 0.07589(18) 0.0331(4) Uani 1 1 d . . . C4 C 0.1004(3) 0.2460(3) 0.38777(17) 0.0418(5) Uani 1 1 d . . . H4A H -0.0629 0.2540 0.3782 0.050 Uiso 1 1 calc R . . H4B H 0.1977 0.3422 0.4570 0.050 Uiso 1 1 calc R . . H4C H 0.1150 0.1187 0.4064 0.050 Uiso 1 1 calc R . . C5 C 0.1390(3) 0.3091(2) -0.04850(17) 0.0355(5) Uani 1 1 d . . . H5 H 0.2667 0.3622 -0.0838 0.043 Uiso 1 1 calc R . . C6 C -0.0849(3) 0.2418(2) -0.13813(17) 0.0318(4) Uani 1 1 d . . . C7 C -0.2899(3) 0.1439(2) -0.10682(17) 0.0351(4) Uani 1 1 d . . . H7 H -0.2887 0.1206 -0.0226 0.042 Uiso 1 1 calc R . . C8 C -0.4927(3) 0.0817(2) -0.19814(17) 0.0380(5) Uani 1 1 d . . . H8 H -0.6297 0.0132 -0.1766 0.046 Uiso 1 1 calc R . . C9 C -0.4993(3) 0.1180(3) -0.32120(17) 0.0415(5) Uani 1 1 d . . . H9 H -0.6401 0.0754 -0.3833 0.050 Uiso 1 1 calc R . . C10 C -0.2993(3) 0.2165(3) -0.35276(18) 0.0426(5) Uani 1 1 d . . . H10 H -0.3030 0.2433 -0.4365 0.051 Uiso 1 1 calc R . . C11 C -0.0937(3) 0.2759(2) -0.26227(17) 0.0381(5) Uani 1 1 d . . . H11 H 0.0437 0.3409 -0.2851 0.046 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 0.0261(6) 0.0428(8) 0.0449(9) 0.0046(6) 0.0060(6) 0.0007(5) O2 0.0307(6) 0.0489(8) 0.0522(9) 0.0004(7) -0.0019(7) 0.0028(6) N 0.0309(7) 0.0304(8) 0.0353(9) 0.0027(7) 0.0066(7) 0.0041(6) C1 0.0309(9) 0.0313(10) 0.0413(12) 0.0023(8) 0.0039(9) 0.0046(7) C2 0.0290(8) 0.0289(9) 0.0366(11) 0.0012(8) 0.0025(8) 0.0045(7) C3 0.0270(8) 0.0285(9) 0.0406(11) 0.0015(8) 0.0061(8) 0.0021(7) C4 0.0373(9) 0.0480(12) 0.0371(12) 0.0069(9) 0.0043(9) 0.0063(8) C5 0.0325(9) 0.0329(10) 0.0423(12) 0.0072(8) 0.0144(9) 0.0035(7) C6 0.0350(9) 0.0257(9) 0.0348(11) 0.0025(8) 0.0098(8) 0.0063(7) C7 0.0363(9) 0.0348(10) 0.0335(11) 0.0041(8) 0.0103(8) 0.0043(7) C8 0.0336(9) 0.0383(10) 0.0395(12) 0.0050(9) 0.0080(8) 0.0025(8) C9 0.0404(10) 0.0403(11) 0.0388(12) 0.0035(9) 0.0014(9) 0.0054(8) C10 0.0546(11) 0.0397(11) 0.0323(11) 0.0071(9) 0.0100(9) 0.0072(9) C11 0.0422(10) 0.0324(10) 0.0413(12) 0.0068(9) 0.0166(9) 0.0045(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.367(2) . ? O1 C3 1.4023(19) . ? O2 C1 1.201(2) . ? N C2 1.288(2) . ? N C3 1.389(2) . ? C1 C2 1.486(2) . ? C2 C4 1.482(2) . ? C3 C5 1.337(2) . ? C5 C6 1.461(2) . ? C6 C11 1.395(2) . ? C6 C7 1.405(2) . ? C7 C8 1.379(2) . ? C8 C9 1.389(2) . ? C9 C10 1.384(2) . ? C10 C11 1.384(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C3 106.73(12) . . ? C2 N C3 107.19(13) . . ? O2 C1 O1 123.44(15) . . ? O2 C1 C2 131.63(18) . . ? O1 C1 C2 104.92(14) . . ? N C2 C4 126.41(14) . . ? N C2 C1 110.61(15) . . ? C4 C2 C1 122.97(16) . . ? C5 C3 N 130.54(16) . . ? C5 C3 O1 118.89(15) . . ? N C3 O1 110.54(15) . . ? C3 C5 C6 129.59(15) . . ? C11 C6 C7 118.41(16) . . ? C11 C6 C5 117.66(15) . . ? C7 C6 C5 123.94(16) . . ? C8 C7 C6 120.10(17) . . ? C7 C8 C9 120.82(16) . . ? C10 C9 C8 119.58(17) . . ? C9 C10 C11 119.96(17) . . ? C10 C11 C6 121.11(16) . . ? 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 C3 O1 C1 O2 179.42(16) . . . . ? C3 O1 C1 C2 -0.59(17) . . . . ? C3 N C2 C4 178.25(17) . . . . ? C3 N C2 C1 -0.90(19) . . . . ? O2 C1 C2 N -179.05(18) . . . . ? O1 C1 C2 N 0.97(19) . . . . ? O2 C1 C2 C4 1.8(3) . . . . ? O1 C1 C2 C4 -178.22(16) . . . . ? C2 N C3 C5 -177.53(19) . . . . ? C2 N C3 O1 0.52(19) . . . . ? C1 O1 C3 C5 178.41(16) . . . . ? C1 O1 C3 N 0.10(18) . . . . ? N C3 C5 C6 -3.0(3) . . . . ? O1 C3 C5 C6 179.13(15) . . . . ? C3 C5 C6 C11 174.79(18) . . . . ? C3 C5 C6 C7 -5.8(3) . . . . ? C11 C6 C7 C8 0.8(3) . . . . ? C5 C6 C7 C8 -178.56(16) . . . . ? C6 C7 C8 C9 -1.4(3) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C6 -1.4(3) . . . . ? C7 C6 C11 C10 0.5(3) . . . . ? C5 C6 C11 C10 179.96(15) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.251 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.108 #===END