# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Ferenc Fulop' 'Szilvia Gyonfalvi' 'Ivan Kanizsai' 'Reijo Sillanpaa' 'Zsolt Szakonyi' _publ_contact_author_name 'Ferenc Fulop' _publ_contact_author_address ; Institute of Pharmaceutical Chemistry University of Szeged Eotvos u. 6. Szeged 6720 HUNGARY ; _publ_contact_author_email FULOP@PHARM.U-SZEGED.HU _publ_requested_journal 'Green Chemistry' _publ_section_title ; Synthesis of Bi- and Tricyclic beta-Lactam Libraries in Aqueous Medium ; data_gy424=2n _database_code_depnum_ccdc_archive 'CCDC 625418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 N2 O3' _chemical_formula_sum 'C21 H26 N2 O3' _chemical_formula_weight 354.44 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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4031(5) _cell_length_b 9.3855(5) _cell_length_c 11.0060(6) _cell_angle_alpha 78.010(3) _cell_angle_beta 84.307(3) _cell_angle_gamma 82.744(3) _cell_volume 939.84(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_wavelength 0.71073 _cell_measurement_reflns_used 3134 _cell_measurement_theta_max 26.733 _cell_measurement_theta_min 0.407 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.084 _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 173(2) _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_decay_% ? _diffrn_reflns_number 5817 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.63 _reflns_number_total 3897 _reflns_number_gt 2543 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0150P)^2^+1.0051P] 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 3897 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 O4 O 0.6497(2) 0.0367(2) 0.08681(17) 0.0386(5) Uani 1 1 d . . . O11 O 0.27098(19) -0.2933(2) 0.33690(17) 0.0362(5) Uani 1 1 d . . . O23 O 0.8293(2) -0.7335(2) 0.27315(18) 0.0388(5) Uani 1 1 d . . . N3 N 0.4864(2) -0.0884(2) 0.23247(19) 0.0276(5) Uani 1 1 d . . . N12 N 0.2042(2) -0.2197(2) 0.1377(2) 0.0275(5) Uani 1 1 d . . . H12 H 0.238(3) -0.179(3) 0.060(3) 0.036(8) Uiso 1 1 d . . . C1 C 0.2690(3) 0.0574(3) 0.3317(2) 0.0321(6) Uani 1 1 d . . . H1 H 0.1904 -0.0074 0.3404 0.039 Uiso 1 1 calc R . . C2 C 0.4239(3) -0.0203(3) 0.3392(2) 0.0289(6) Uani 1 1 d . . . H2 H 0.4477 -0.0775 0.4233 0.035 Uiso 1 1 calc R . . C4 C 0.5695(3) 0.0205(3) 0.1816(2) 0.0305(6) Uani 1 1 d . . . C5 C 0.5186(3) 0.1067(3) 0.2836(3) 0.0333(6) Uani 1 1 d . . . H5 H 0.5943 0.1194 0.3370 0.040 Uiso 1 1 calc R . . C6 C 0.4048(3) 0.2407(3) 0.2508(3) 0.0345(6) Uani 1 1 d . . . H6 H 0.4388 0.3279 0.1916 0.041 Uiso 1 1 calc R . . C7 C 0.3379(3) 0.2665(3) 0.3764(3) 0.0430(7) Uani 1 1 d . . . H7 H 0.3498 0.3466 0.4135 0.052 Uiso 1 1 calc R . . C8 C 0.2597(3) 0.1575(3) 0.4255(3) 0.0399(7) Uani 1 1 d . . . H8 H 0.2074 0.1443 0.5047 0.048 Uiso 1 1 calc R . . C9 C 0.2823(3) 0.1703(3) 0.2095(3) 0.0335(6) Uani 1 1 d . . . H9A H 0.1940 0.2391 0.1946 0.040 Uiso 1 1 calc R . . H9B H 0.3121 0.1247 0.1362 0.040 Uiso 1 1 calc R . . C10 C 0.4519(3) -0.2080(3) 0.1782(2) 0.0276(6) Uani 1 1 d . . . H10 H 0.4548 -0.1745 0.0856 0.033 Uiso 1 1 calc R . . C11 C 0.2985(3) -0.2439(3) 0.2260(2) 0.0273(6) Uani 1 1 d . . . C13 C 0.0557(3) -0.2628(3) 0.1603(3) 0.0332(6) Uani 1 1 d . . . C14 C -0.0120(3) -0.2224(4) 0.0357(3) 0.0424(7) Uani 1 1 d . . . H14A H 0.0451 -0.2746 -0.0242 0.064 Uiso 1 1 calc R . . H14B H -0.0143 -0.1166 0.0043 0.064 Uiso 1 1 calc R . . H14C H -0.1102 -0.2502 0.0469 0.064 Uiso 1 1 calc R . . C15 C 0.0628(4) -0.4280(4) 0.2077(3) 0.0544(9) Uani 1 1 d . . . H15A H 0.1071 -0.4539 0.2874 0.082 Uiso 1 1 calc R . . H15B H 0.1205 -0.4783 0.1469 0.082 Uiso 1 1 calc R . . H15C H -0.0346 -0.4578 0.2192 0.082 Uiso 1 1 calc R . . C16 C -0.0323(3) -0.1797(4) 0.2525(3) 0.0499(9) Uani 1 1 d . . . H16A H -0.0356 -0.0741 0.2193 0.075 Uiso 1 1 calc R . . H16B H 0.0125 -0.2033 0.3320 0.075 Uiso 1 1 calc R . . H16C H -0.1302 -0.2082 0.2655 0.075 Uiso 1 1 calc R . . C17 C 0.5553(3) -0.3457(3) 0.2075(2) 0.0267(6) Uani 1 1 d . . . C18 C 0.6089(3) -0.4207(3) 0.1131(2) 0.0325(6) Uani 1 1 d . . . H18 H 0.5835 -0.3824 0.0303 0.039 Uiso 1 1 calc R . . C19 C 0.6985(3) -0.5498(3) 0.1382(3) 0.0349(6) Uani 1 1 d . . . H19 H 0.7332 -0.6003 0.0730 0.042 Uiso 1 1 calc R . . C20 C 0.7380(3) -0.6061(3) 0.2585(2) 0.0295(6) Uani 1 1 d . . . C21 C 0.6847(3) -0.5338(3) 0.3540(2) 0.0327(6) Uani 1 1 d . . . H21 H 0.7100 -0.5722 0.4369 0.039 Uiso 1 1 calc R . . C22 C 0.5942(3) -0.4047(3) 0.3273(2) 0.0314(6) Uani 1 1 d . . . H22 H 0.5579 -0.3553 0.3928 0.038 Uiso 1 1 calc R . . C24 C 0.8808(3) -0.7879(3) 0.3930(3) 0.0452(8) Uani 1 1 d . . . H24A H 0.7992 -0.8057 0.4548 0.068 Uiso 1 1 calc R . . H24B H 0.9357 -0.7158 0.4145 0.068 Uiso 1 1 calc R . . H24C H 0.9430 -0.8798 0.3923 0.068 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 O4 0.0296(10) 0.0503(13) 0.0324(11) 0.0040(9) 0.0004(9) -0.0137(9) O11 0.0305(10) 0.0486(12) 0.0252(10) 0.0049(9) -0.0008(8) -0.0098(9) O23 0.0356(11) 0.0383(11) 0.0400(12) -0.0083(9) -0.0006(9) 0.0040(9) N3 0.0248(11) 0.0297(12) 0.0264(11) 0.0003(10) -0.0003(9) -0.0070(9) N12 0.0230(11) 0.0305(12) 0.0293(12) -0.0046(10) -0.0020(9) -0.0065(9) C1 0.0305(14) 0.0336(15) 0.0328(15) -0.0080(13) -0.0028(12) -0.0034(12) C2 0.0291(14) 0.0336(15) 0.0238(13) -0.0020(12) -0.0040(11) -0.0075(11) C4 0.0241(13) 0.0343(15) 0.0309(15) 0.0031(12) -0.0076(11) -0.0069(11) C5 0.0323(14) 0.0358(16) 0.0325(15) 0.0003(12) -0.0099(12) -0.0125(12) C6 0.0448(17) 0.0259(14) 0.0336(15) 0.0001(12) -0.0116(13) -0.0091(12) C7 0.0510(19) 0.0403(18) 0.0418(17) -0.0137(15) -0.0163(15) -0.0009(15) C8 0.0376(16) 0.0467(18) 0.0355(16) -0.0124(14) -0.0049(13) 0.0036(14) C9 0.0349(15) 0.0325(15) 0.0330(15) -0.0031(12) -0.0128(12) -0.0006(12) C10 0.0263(13) 0.0334(15) 0.0223(13) -0.0011(11) -0.0029(11) -0.0066(11) C11 0.0245(13) 0.0274(14) 0.0298(14) -0.0042(12) -0.0021(11) -0.0038(11) C13 0.0230(13) 0.0408(16) 0.0371(15) -0.0067(13) -0.0025(12) -0.0095(12) C14 0.0290(15) 0.059(2) 0.0431(18) -0.0146(16) -0.0095(13) -0.0048(14) C15 0.0479(19) 0.0446(19) 0.070(2) 0.0037(18) -0.0106(17) -0.0239(16) C16 0.0258(15) 0.083(3) 0.0440(18) -0.0227(18) 0.0009(13) -0.0024(15) C17 0.0226(12) 0.0334(15) 0.0248(13) -0.0054(12) -0.0007(10) -0.0072(11) C18 0.0321(14) 0.0440(17) 0.0226(13) -0.0063(12) -0.0013(11) -0.0095(13) C19 0.0369(15) 0.0402(17) 0.0304(15) -0.0145(13) -0.0008(12) -0.0034(13) C20 0.0231(13) 0.0314(15) 0.0340(15) -0.0048(12) -0.0011(11) -0.0068(11) C21 0.0318(14) 0.0394(16) 0.0253(14) -0.0034(12) -0.0040(12) -0.0017(12) C22 0.0325(15) 0.0374(16) 0.0242(13) -0.0085(12) -0.0034(11) 0.0015(12) C24 0.0427(18) 0.0408(18) 0.0466(19) -0.0003(15) -0.0066(15) 0.0046(14) _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 O4 C4 1.219(3) . ? O11 C11 1.226(3) . ? O23 C20 1.372(3) . ? O23 C24 1.421(3) . ? N3 C4 1.359(3) . ? N3 C10 1.460(3) . ? N3 C2 1.488(3) . ? N12 C11 1.345(3) . ? N12 C13 1.486(3) . ? N12 H12 0.90(3) . ? C1 C8 1.523(4) . ? C1 C9 1.535(4) . ? C1 C2 1.545(4) . ? C1 H1 1.0000 . ? C2 C5 1.564(3) . ? C2 H2 1.0000 . ? C4 C5 1.522(4) . ? C5 C6 1.551(4) . ? C5 H5 1.0000 . ? C6 C7 1.514(4) . ? C6 C9 1.546(4) . ? C6 H6 1.0000 . ? C7 C8 1.327(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C17 1.513(4) . ? C10 C11 1.540(3) . ? C10 H10 1.0000 . ? C13 C16 1.524(4) . ? C13 C14 1.524(4) . ? C13 C15 1.525(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.386(4) . ? C17 C18 1.392(3) . ? C18 C19 1.380(4) . ? C18 H18 0.9500 . ? C19 C20 1.388(4) . ? C19 H19 0.9500 . ? C20 C21 1.387(4) . ? C21 C22 1.385(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C20 O23 C24 117.0(2) . . ? C4 N3 C10 128.8(2) . . ? C4 N3 C2 95.0(2) . . ? C10 N3 C2 134.72(19) . . ? C11 N12 C13 123.9(2) . . ? C11 N12 H12 115.5(18) . . ? C13 N12 H12 120.5(18) . . ? C8 C1 C9 100.1(2) . . ? C8 C1 C2 103.3(2) . . ? C9 C1 C2 101.9(2) . . ? C8 C1 H1 116.4 . . ? C9 C1 H1 116.4 . . ? C2 C1 H1 116.4 . . ? N3 C2 C1 117.3(2) . . ? N3 C2 C5 86.39(18) . . ? C1 C2 C5 103.1(2) . . ? N3 C2 H2 115.3 . . ? C1 C2 H2 115.3 . . ? C5 C2 H2 115.3 . . ? O4 C4 N3 130.6(3) . . ? O4 C4 C5 136.6(2) . . ? N3 C4 C5 92.8(2) . . ? C4 C5 C6 116.9(2) . . ? C4 C5 C2 85.80(19) . . ? C6 C5 C2 102.6(2) . . ? C4 C5 H5 115.6 . . ? C6 C5 H5 115.6 . . ? C2 C5 H5 115.6 . . ? C7 C6 C9 99.6(2) . . ? C7 C6 C5 103.9(2) . . ? C9 C6 C5 101.8(2) . . ? C7 C6 H6 116.4 . . ? C9 C6 H6 116.4 . . ? C5 C6 H6 116.4 . . ? C8 C7 C6 108.0(3) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? C7 C8 C1 107.5(3) . . ? C7 C8 H8 126.2 . . ? C1 C8 H8 126.2 . . ? C1 C9 C6 94.0(2) . . ? C1 C9 H9A 112.9 . . ? C6 C9 H9A 112.9 . . ? C1 C9 H9B 112.9 . . ? C6 C9 H9B 112.9 . . ? H9A C9 H9B 110.3 . . ? N3 C10 C17 113.3(2) . . ? N3 C10 C11 109.1(2) . . ? C17 C10 C11 109.1(2) . . ? N3 C10 H10 108.4 . . ? C17 C10 H10 108.4 . . ? C11 C10 H10 108.4 . . ? O11 C11 N12 125.1(2) . . ? O11 C11 C10 119.9(2) . . ? N12 C11 C10 114.9(2) . . ? N12 C13 C16 110.4(2) . . ? N12 C13 C14 107.2(2) . . ? C16 C13 C14 109.3(2) . . ? N12 C13 C15 109.0(2) . . ? C16 C13 C15 111.3(3) . . ? C14 C13 C15 109.5(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 118.1(3) . . ? C22 C17 C10 122.2(2) . . ? C18 C17 C10 119.7(2) . . ? C19 C18 C17 120.9(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? O23 C20 C21 124.6(2) . . ? O23 C20 C19 115.6(2) . . ? C21 C20 C19 119.8(3) . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C17 121.8(2) . . ? C21 C22 H22 119.1 . . ? C17 C22 H22 119.1 . . ? O23 C24 H24A 109.5 . . ? O23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 C1 102.6(2) . . . . ? C10 N3 C2 C1 -63.9(4) . . . . ? C4 N3 C2 C5 -0.2(2) . . . . ? C10 N3 C2 C5 -166.8(3) . . . . ? C8 C1 C2 N3 -160.4(2) . . . . ? C9 C1 C2 N3 -56.8(3) . . . . ? C8 C1 C2 C5 -67.6(3) . . . . ? C9 C1 C2 C5 35.9(2) . . . . ? C10 N3 C4 O4 -10.4(5) . . . . ? C2 N3 C4 O4 -178.1(3) . . . . ? C10 N3 C4 C5 168.0(2) . . . . ? C2 N3 C4 C5 0.2(2) . . . . ? O4 C4 C5 C6 75.9(4) . . . . ? N3 C4 C5 C6 -102.3(2) . . . . ? O4 C4 C5 C2 178.0(3) . . . . ? N3 C4 C5 C2 -0.2(2) . . . . ? N3 C2 C5 C4 0.22(18) . . . . ? C1 C2 C5 C4 -117.0(2) . . . . ? N3 C2 C5 C6 116.9(2) . . . . ? C1 C2 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C7 159.8(2) . . . . ? C2 C5 C6 C7 68.1(2) . . . . ? C4 C5 C6 C9 56.7(3) . . . . ? C2 C5 C6 C9 -35.0(3) . . . . ? C9 C6 C7 C8 34.5(3) . . . . ? C5 C6 C7 C8 -70.4(3) . . . . ? C6 C7 C8 C1 -1.5(3) . . . . ? C9 C1 C8 C7 -32.3(3) . . . . ? C2 C1 C8 C7 72.6(3) . . . . ? C8 C1 C9 C6 49.8(2) . . . . ? C2 C1 C9 C6 -56.2(2) . . . . ? C7 C6 C9 C1 -50.6(2) . . . . ? C5 C6 C9 C1 55.9(2) . . . . ? C4 N3 C10 C17 91.7(3) . . . . ? C2 N3 C10 C17 -105.6(3) . . . . ? C4 N3 C10 C11 -146.5(3) . . . . ? C2 N3 C10 C11 16.2(4) . . . . ? C13 N12 C11 O11 -6.0(4) . . . . ? C13 N12 C11 C10 172.6(2) . . . . ? N3 C10 C11 O11 -65.2(3) . . . . ? C17 C10 C11 O11 59.1(3) . . . . ? N3 C10 C11 N12 116.1(2) . . . . ? C17 C10 C11 N12 -119.5(2) . . . . ? C11 N12 C13 C16 63.7(3) . . . . ? C11 N12 C13 C14 -177.4(2) . . . . ? C11 N12 C13 C15 -58.9(3) . . . . ? N3 C10 C17 C22 48.4(3) . . . . ? C11 C10 C17 C22 -73.4(3) . . . . ? N3 C10 C17 C18 -134.6(2) . . . . ? C11 C10 C17 C18 103.6(3) . . . . ? C22 C17 C18 C19 -0.1(4) . . . . ? C10 C17 C18 C19 -177.2(2) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? C24 O23 C20 C21 -5.0(4) . . . . ? C24 O23 C20 C19 175.2(2) . . . . ? C18 C19 C20 O23 -178.9(2) . . . . ? C18 C19 C20 C21 1.3(4) . . . . ? O23 C20 C21 C22 179.3(2) . . . . ? C19 C20 C21 C22 -0.9(4) . . . . ? C20 C21 C22 C17 0.0(4) . . . . ? C18 C17 C22 C21 0.5(4) . . . . ? C10 C17 C22 C21 177.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12 O4 0.90(3) 2.15(3) 3.017(3) 160(2) 2_655 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.63 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.213 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.050