Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Matthias Beller' _publ_contact_author_address ; Leibniz-Institut fur Organische Katalyse der Universitat Rostock Albert-Einstein-Strasse 29a Rostock 18059 GERMANY ; _publ_contact_author_email MATTHIAS.BELLER@IFOK-ROSTOCK.DE _publ_section_title ; Synthesis and antimicrobial activity of N-analogous corollosporines ; loop_ _publ_author_name 'Matthias Beller' 'Sandra Hubner' 'Stefan Klaus' 'Michael Lalk' 'Ulrike Lindequist' 'Helfried Neumann' ; A.Spannenberg ; 'Dirk Strubing' # Attachment 'ks145.cif' data_ks145 _database_code_depnum_ccdc_archive 'CCDC 292373' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 N2 O2' _chemical_formula_weight 262.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.365(3) _cell_length_b 8.446(2) _cell_length_c 12.304(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.88(3) _cell_angle_gamma 90.00 _cell_volume 1478.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 STOE-IPDSI _diffrn_measurement_method 'laser scanned imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 360 _diffrn_standards_decay_% ? _diffrn_reflns_number 3738 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 23.00 _reflns_number_total 2051 _reflns_number_gt 1608 _reflns_threshold_expression >2sigma(I) _computing_data_collection STOE-EXPOSE _computing_cell_refinement STOE-CELL _computing_data_reduction STOE-INTEGRATE _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1183P)^2^+0.8155P] 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 2051 _refine_ls_number_parameters 182 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1930 _refine_ls_wR_factor_gt 0.1849 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C10A C 0.5517(4) 0.6251(13) 0.8688(9) 0.079(3) Uiso 0.50 1 d PD A 1 H10A H 0.5846 0.5358 0.9096 0.095 Uiso 0.50 1 calc PR A 1 H10B H 0.5864 0.6587 0.8085 0.095 Uiso 0.50 1 calc PR A 1 C11A C 0.5322(8) 0.7645(14) 0.9448(8) 0.074(3) Uiso 0.50 1 d PD A 1 H11A H 0.5920 0.8077 0.9805 0.110 Uiso 0.50 1 calc PR A 1 H11B H 0.4953 0.7263 1.0008 0.110 Uiso 0.50 1 calc PR A 1 H11C H 0.4971 0.8474 0.9011 0.110 Uiso 0.50 1 calc PR A 1 C10B C 0.5343(5) 0.6727(11) 0.8903(8) 0.059(3) Uiso 0.50 1 d PD A 2 H10C H 0.5636 0.5997 0.9481 0.071 Uiso 0.50 1 calc PR A 2 H10D H 0.5799 0.6875 0.8378 0.071 Uiso 0.50 1 calc PR A 2 C11B C 0.5216(11) 0.8353(16) 0.9455(12) 0.117(5) Uiso 0.50 1 d PD A 2 H11D H 0.5827 0.8734 0.9810 0.175 Uiso 0.50 1 calc PR A 2 H11E H 0.4788 0.8234 1.0005 0.175 Uiso 0.50 1 calc PR A 2 H11F H 0.4952 0.9117 0.8896 0.175 Uiso 0.50 1 calc PR A 2 C1 C 0.1699(2) 0.6421(3) 0.5249(2) 0.0262(7) Uani 1 1 d . . . C2 C 0.1878(2) 0.4882(3) 0.4689(2) 0.0274(7) Uani 1 1 d . . . C3 C 0.14412(19) 0.3661(3) 0.5163(2) 0.0274(7) Uani 1 1 d . . . C4 C 0.0898(2) 0.4325(4) 0.5980(2) 0.0267(7) Uani 1 1 d . . . C5 C 0.0654(2) 0.6976(4) 0.6739(3) 0.0383(8) Uani 1 1 d . . . H5A H 0.0859 0.8059 0.6612 0.058 Uiso 1 1 calc R . . H5B H 0.0870 0.6674 0.7501 0.058 Uiso 1 1 calc R . . H5C H -0.0033 0.6921 0.6601 0.058 Uiso 1 1 calc R . . C6 C 0.2587(2) 0.7171(4) 0.5863(2) 0.0319(8) Uani 1 1 d . . . H6A H 0.3031 0.7387 0.5333 0.038 Uiso 1 1 calc R . . H6B H 0.2418 0.8199 0.6169 0.038 Uiso 1 1 calc R . . C7 C 0.3078(2) 0.6167(4) 0.6784(3) 0.0413(9) Uani 1 1 d . . . H7A H 0.3216 0.5116 0.6487 0.050 Uiso 1 1 calc R . . H7B H 0.2647 0.6002 0.7337 0.050 Uiso 1 1 calc R . . C8 C 0.3985(2) 0.6885(4) 0.7343(3) 0.0419(9) Uani 1 1 d . A . H8A H 0.3848 0.7944 0.7629 0.050 Uiso 1 1 calc R . . H8B H 0.4420 0.7031 0.6793 0.050 Uiso 1 1 calc R . . C9 C 0.4467(3) 0.5881(6) 0.8284(4) 0.0798(15) Uani 1 1 d D . . H9A H 0.4419 0.4757 0.8054 0.096 Uiso 1 1 calc R A 1 H9B H 0.4112 0.5998 0.8914 0.096 Uiso 1 1 calc R A 1 C12 C 0.2372(2) 0.4616(5) 0.3821(3) 0.0441(9) Uani 1 1 d . . . H12 H 0.2665 0.5455 0.3481 0.053 Uiso 1 1 calc R . . C13 C 0.2420(3) 0.3046(5) 0.3465(3) 0.0573(11) Uani 1 1 d . . . H13 H 0.2745 0.2821 0.2861 0.069 Uiso 1 1 calc R . . C14 C 0.2013(3) 0.1827(5) 0.3959(3) 0.0557(11) Uani 1 1 d . . . H14 H 0.2076 0.0778 0.3700 0.067 Uiso 1 1 calc R . . C15 C 0.1505(2) 0.2085(4) 0.4836(3) 0.0398(9) Uani 1 1 d . . . N1 N 0.10497(16) 0.5899(3) 0.60038(18) 0.0266(6) Uani 1 1 d . . . N2 N 0.1089(3) 0.0894(4) 0.5336(4) 0.0597(10) Uani 1 1 d . . . O1 O 0.03761(14) 0.3616(3) 0.65400(16) 0.0365(6) Uani 1 1 d . . . O2 O 0.12780(16) 0.7587(2) 0.45196(18) 0.0332(6) Uani 1 1 d . . . HN2A H 0.119(3) -0.013(6) 0.506(4) 0.086(15) Uiso 1 1 d . . . HN2B H 0.080(3) 0.113(6) 0.592(4) 0.070(15) Uiso 1 1 d . . . HO2 H 0.083(3) 0.724(5) 0.418(3) 0.054(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0328(16) 0.0211(15) 0.0252(15) 0.0047(12) 0.0055(13) -0.0006(13) C2 0.0275(15) 0.0292(17) 0.0252(15) -0.0018(13) 0.0021(13) 0.0002(13) C3 0.0281(15) 0.0223(16) 0.0306(16) -0.0010(13) 0.0000(13) 0.0041(12) C4 0.0293(16) 0.0263(17) 0.0227(14) 0.0043(13) -0.0024(13) -0.0014(13) C5 0.0415(18) 0.0418(19) 0.0328(17) -0.0136(15) 0.0089(14) 0.0029(15) C6 0.0348(17) 0.0262(16) 0.0344(16) 0.0019(14) 0.0033(14) -0.0043(13) C7 0.0413(19) 0.0362(19) 0.0428(18) 0.0058(16) -0.0068(15) -0.0050(15) C8 0.0364(18) 0.049(2) 0.0388(18) 0.0024(16) -0.0007(15) -0.0052(16) C9 0.072(3) 0.079(3) 0.076(3) 0.022(3) -0.035(3) -0.015(2) C12 0.043(2) 0.054(2) 0.0389(18) -0.0042(17) 0.0145(16) -0.0012(17) C13 0.051(2) 0.073(3) 0.050(2) -0.029(2) 0.0151(18) 0.012(2) C14 0.050(2) 0.045(2) 0.069(3) -0.029(2) -0.002(2) 0.0118(19) C15 0.0365(18) 0.0265(18) 0.053(2) -0.0090(16) -0.0049(16) 0.0045(15) N1 0.0321(14) 0.0232(14) 0.0258(13) -0.0031(10) 0.0088(11) -0.0003(10) N2 0.069(2) 0.0190(17) 0.091(3) -0.0038(18) 0.008(2) -0.0025(15) O1 0.0357(12) 0.0412(13) 0.0320(12) 0.0129(10) 0.0027(10) -0.0122(10) O2 0.0382(13) 0.0245(12) 0.0346(12) 0.0073(10) -0.0036(10) -0.0061(10) _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 C10A C11A 1.553(6) . ? C10A C9 1.553(6) . ? C10B C11B 1.553(6) . ? C10B C9 1.553(6) . ? C1 O2 1.411(4) . ? C1 N1 1.471(4) . ? C1 C2 1.510(4) . ? C1 C6 1.528(4) . ? C2 C3 1.377(4) . ? C2 C12 1.379(4) . ? C3 C15 1.398(4) . ? C3 C4 1.466(4) . ? C4 O1 1.240(3) . ? C4 N1 1.347(4) . ? C5 N1 1.452(4) . ? C6 C7 1.511(4) . ? C7 C8 1.514(4) . ? C8 C9 1.523(5) . ? C12 C13 1.401(6) . ? C13 C14 1.367(6) . ? C14 C15 1.400(5) . ? C15 N2 1.359(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11A C10A C9 95.6(7) . . ? C11B C10B C9 119.0(9) . . ? O2 C1 N1 110.9(2) . . ? O2 C1 C2 113.3(2) . . ? N1 C1 C2 101.1(2) . . ? O2 C1 C6 106.3(2) . . ? N1 C1 C6 111.8(2) . . ? C2 C1 C6 113.5(2) . . ? C3 C2 C12 121.2(3) . . ? C3 C2 C1 109.6(2) . . ? C12 C2 C1 129.2(3) . . ? C2 C3 C15 122.7(3) . . ? C2 C3 C4 108.7(3) . . ? C15 C3 C4 128.6(3) . . ? O1 C4 N1 125.0(3) . . ? O1 C4 C3 128.0(3) . . ? N1 C4 C3 107.0(2) . . ? C7 C6 C1 114.2(2) . . ? C6 C7 C8 113.6(3) . . ? C7 C8 C9 113.3(3) . . ? C8 C9 C10B 111.8(5) . . ? C8 C9 C10A 116.9(5) . . ? C10B C9 C10A 20.7(4) . . ? C2 C12 C13 116.6(3) . . ? C14 C13 C12 122.1(3) . . ? C13 C14 C15 121.7(3) . . ? N2 C15 C3 121.6(3) . . ? N2 C15 C14 122.8(3) . . ? C3 C15 C14 115.6(3) . . ? C4 N1 C5 123.8(2) . . ? C4 N1 C1 113.4(2) . . ? C5 N1 C1 122.8(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.626 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.055 # Attachment 'ks231.cif' data_ks231 _database_code_depnum_ccdc_archive 'CCDC 292374' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 N2 O3' _chemical_formula_weight 304.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.917(2) _cell_length_b 8.949(2) _cell_length_c 10.953(2) _cell_angle_alpha 96.61(3) _cell_angle_beta 97.73(3) _cell_angle_gamma 99.99(3) _cell_volume 844.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type STOE-IPDSI _diffrn_measurement_method 'laser scanned imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 360 _diffrn_standards_decay_% ? _diffrn_reflns_number 4524 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 24.26 _reflns_number_total 2510 _reflns_number_gt 1344 _reflns_threshold_expression >2sigma(I) _computing_data_collection STOE-EXPOSE _computing_cell_refinement STOE-CELL _computing_data_reduction STOE-INTEGRATE _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^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 2510 _refine_ls_number_parameters 205 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 0.860 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C16A C 0.3947(10) -0.3221(6) 0.6269(6) 0.126(3) Uiso 0.70 1 d PD A 1 H16A H 0.2963 -0.2929 0.6026 0.151 Uiso 0.70 1 calc PR A 1 H16B H 0.4482 -0.3241 0.5554 0.151 Uiso 0.70 1 calc PR A 1 C17A C 0.3674(9) -0.4796(8) 0.6655(8) 0.145(3) Uiso 0.70 1 d PD A 1 H17A H 0.3075 -0.5517 0.5973 0.218 Uiso 0.70 1 calc PR A 1 H17B H 0.3126 -0.4783 0.7352 0.218 Uiso 0.70 1 calc PR A 1 H17C H 0.4646 -0.5092 0.6886 0.218 Uiso 0.70 1 calc PR A 1 C16B C 0.3598(12) -0.3323(16) 0.6656(19) 0.148(9) Uiso 0.30 1 d PD A 2 H16C H 0.3126 -0.3937 0.7227 0.178 Uiso 0.30 1 calc PR A 2 H16D H 0.2815 -0.2944 0.6141 0.178 Uiso 0.30 1 calc PR A 2 C17B C 0.4555(19) -0.417(2) 0.5894(14) 0.129(5) Uiso 0.30 1 d PD A 2 H17D H 0.3905 -0.5056 0.5390 0.193 Uiso 0.30 1 calc PR A 2 H17E H 0.5338 -0.4489 0.6440 0.193 Uiso 0.30 1 calc PR A 2 H17F H 0.5031 -0.3509 0.5368 0.193 Uiso 0.30 1 calc PR A 2 C1 C 0.8345(3) 0.3224(3) 0.7967(2) 0.0561(8) Uani 1 1 d . . . C2 C 0.9796(3) 0.2587(3) 0.8274(2) 0.0529(7) Uani 1 1 d . . . C3 C 1.0764(3) 0.2112(3) 0.7486(3) 0.0581(8) Uani 1 1 d . . . C4 C 1.1976(4) 0.1475(4) 0.8009(3) 0.0708(9) Uani 1 1 d . . . H4 H 1.2641 0.1127 0.7505 0.085 Uiso 1 1 calc R . . C5 C 1.2208(4) 0.1351(4) 0.9264(3) 0.0743(10) Uani 1 1 d . . . H5 H 1.3009 0.0895 0.9582 0.089 Uiso 1 1 calc R . . C6 C 1.1283(4) 0.1884(4) 1.0053(3) 0.0675(9) Uani 1 1 d . . . H6 H 1.1455 0.1821 1.0900 0.081 Uiso 1 1 calc R . . C7 C 1.0088(3) 0.2518(3) 0.9534(2) 0.0550(8) Uani 1 1 d . . . C8 C 0.8952(4) 0.3225(3) 1.0141(3) 0.0611(8) Uani 1 1 d . . . C9 C 1.1123(4) 0.1727(4) 0.5255(3) 0.0723(9) Uani 1 1 d . . . C10 C 1.0624(5) 0.2258(5) 0.4044(3) 0.0932(12) Uani 1 1 d . . . H10A H 0.9954 0.2974 0.4170 0.140 Uiso 1 1 calc R . . H10B H 1.0084 0.1394 0.3452 0.140 Uiso 1 1 calc R . . H10C H 1.1513 0.2746 0.3734 0.140 Uiso 1 1 calc R . . C11 C 0.6657(4) 0.4290(4) 0.9446(3) 0.0793(10) Uani 1 1 d . . . H11A H 0.6142 0.4492 0.8672 0.119 Uiso 1 1 calc R . . H11B H 0.6983 0.5230 1.0011 0.119 Uiso 1 1 calc R . . H11C H 0.5962 0.3581 0.9801 0.119 Uiso 1 1 calc R . . C12 C 0.7029(3) 0.2065(3) 0.7159(3) 0.0632(9) Uani 1 1 d D . . H12A H 0.6152 0.2560 0.6996 0.076 Uiso 1 1 calc R . . H12B H 0.7347 0.1778 0.6366 0.076 Uiso 1 1 calc R . . C13 C 0.6516(4) 0.0627(3) 0.7705(3) 0.0726(9) Uani 1 1 d D . . H13A H 0.7415 0.0213 0.7991 0.087 Uiso 1 1 calc R . . H13B H 0.6035 0.0889 0.8424 0.087 Uiso 1 1 calc R . . C14 C 0.5397(3) -0.0590(3) 0.6802(3) 0.0740(9) Uani 1 1 d D A . H14A H 0.5872 -0.0829 0.6076 0.089 Uiso 1 1 calc R . . H14B H 0.4491 -0.0177 0.6531 0.089 Uiso 1 1 calc R . . C15 C 0.4890(5) -0.2055(4) 0.7315(4) 0.1124(15) Uani 1 1 d D . . H15A H 0.4277 -0.1870 0.7965 0.135 Uiso 1 1 calc R A 1 H15B H 0.5783 -0.2432 0.7671 0.135 Uiso 1 1 calc R A 1 N1 N 0.7992(3) 0.3633(3) 0.9227(2) 0.0606(7) Uani 1 1 d . . . N2 N 1.0503(3) 0.2326(3) 0.6227(2) 0.0666(8) Uani 1 1 d . . . O1 O 0.8576(3) 0.4518(3) 0.7338(2) 0.0668(6) Uani 1 1 d . . . O2 O 0.8891(3) 0.3451(3) 1.12614(19) 0.0751(7) Uani 1 1 d . . . O3 O 1.1968(3) 0.0825(4) 0.5360(2) 0.0997(9) Uani 1 1 d . . . HN2 H 0.995(4) 0.293(4) 0.613(3) 0.068(11) Uiso 1 1 d . . . HO1 H 0.937(4) 0.528(5) 0.775(3) 0.107(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.069(2) 0.0580(19) 0.0480(16) 0.0164(16) 0.0142(14) 0.0199(16) C2 0.0604(18) 0.0542(19) 0.0471(16) 0.0124(15) 0.0110(14) 0.0137(14) C3 0.067(2) 0.061(2) 0.0498(17) 0.0135(16) 0.0116(15) 0.0171(16) C4 0.067(2) 0.084(2) 0.069(2) 0.0126(19) 0.0183(16) 0.0300(18) C5 0.075(2) 0.085(3) 0.070(2) 0.018(2) 0.0042(18) 0.0358(19) C6 0.081(2) 0.071(2) 0.0527(18) 0.0204(17) 0.0035(16) 0.0175(18) C7 0.0639(19) 0.0555(19) 0.0472(16) 0.0121(15) 0.0098(14) 0.0121(15) C8 0.076(2) 0.058(2) 0.0519(19) 0.0152(16) 0.0182(16) 0.0087(16) C9 0.082(2) 0.079(3) 0.062(2) 0.0131(19) 0.0284(18) 0.016(2) C10 0.125(3) 0.106(3) 0.0544(19) 0.016(2) 0.031(2) 0.022(2) C11 0.081(2) 0.080(3) 0.088(2) 0.009(2) 0.0317(19) 0.0324(19) C12 0.066(2) 0.074(2) 0.0547(17) 0.0169(17) 0.0066(15) 0.0246(17) C13 0.081(2) 0.071(2) 0.0641(19) 0.0140(18) 0.0042(17) 0.0134(18) C14 0.062(2) 0.081(2) 0.073(2) 0.000(2) 0.0035(17) 0.0119(18) C15 0.117(3) 0.090(3) 0.101(3) -0.002(3) -0.019(3) -0.023(3) N1 0.0706(17) 0.0644(17) 0.0544(15) 0.0120(13) 0.0201(12) 0.0233(13) N2 0.082(2) 0.075(2) 0.0518(16) 0.0144(15) 0.0212(14) 0.0298(17) O1 0.0865(17) 0.0605(14) 0.0603(13) 0.0235(12) 0.0128(12) 0.0220(13) O2 0.0949(16) 0.0856(17) 0.0477(13) 0.0118(11) 0.0254(11) 0.0124(12) O3 0.115(2) 0.125(2) 0.0798(17) 0.0173(16) 0.0403(15) 0.0594(19) _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 C16A C17A 1.507(2) . ? C16A C15 1.507(2) . ? C16B C17B 1.507(2) . ? C16B C15 1.507(2) . ? C1 O1 1.414(3) . ? C1 N1 1.476(4) . ? C1 C2 1.515(4) . ? C1 C12 1.524(4) . ? C2 C7 1.380(4) . ? C2 C3 1.384(4) . ? C3 C4 1.394(4) . ? C3 N2 1.408(4) . ? C4 C5 1.383(4) . ? C5 C6 1.374(4) . ? C6 C7 1.378(4) . ? C7 C8 1.475(4) . ? C8 O2 1.231(3) . ? C8 N1 1.353(4) . ? C9 O3 1.201(4) . ? C9 N2 1.363(4) . ? C9 C10 1.497(4) . ? C11 N1 1.451(4) . ? C12 C13 1.507(2) . ? C13 C14 1.507(2) . ? C14 C15 1.507(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 C17A C16A C15 111.1(5) . . ? C17B C16B C15 97.0(10) . . ? O1 C1 N1 111.4(2) . . ? O1 C1 C2 113.3(2) . . ? N1 C1 C2 100.7(2) . . ? O1 C1 C12 106.4(2) . . ? N1 C1 C12 111.7(2) . . ? C2 C1 C12 113.5(3) . . ? C7 C2 C3 120.9(3) . . ? C7 C2 C1 110.1(3) . . ? C3 C2 C1 129.0(2) . . ? C2 C3 C4 117.0(2) . . ? C2 C3 N2 119.1(3) . . ? C4 C3 N2 123.9(3) . . ? C5 C4 C3 121.1(3) . . ? C6 C5 C4 121.6(3) . . ? C5 C6 C7 117.1(3) . . ? C6 C7 C2 122.1(3) . . ? C6 C7 C8 129.5(3) . . ? C2 C7 C8 108.4(3) . . ? O2 C8 N1 125.6(3) . . ? O2 C8 C7 127.6(3) . . ? N1 C8 C7 106.8(2) . . ? O3 C9 N2 122.6(3) . . ? O3 C9 C10 123.2(3) . . ? N2 C9 C10 114.2(3) . . ? C13 C12 C1 115.2(2) . . ? C14 C13 C12 113.5(3) . . ? C13 C14 C15 114.7(3) . . ? C14 C15 C16B 123.7(10) . . ? C14 C15 C16A 108.5(4) . . ? C16B C15 C16A 21.6(8) . . ? C8 N1 C11 123.4(3) . . ? C8 N1 C1 113.7(2) . . ? C11 N1 C1 122.7(2) . . ? C9 N2 C3 128.9(3) . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 24.26 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.183 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.035