# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Rosa Claramunt' _publ_contact_author_email RCLARAMUNT@CCIA.UNED.ES _publ_section_title ; The annular tautomerism of the curcuminoid NH-pyrazoles ; loop_ _publ_author_name 'Rosa Claramunt' 'Latifa Bouissane' 'P. Cabildo' 'Pilar Cornago' 'J Elguero' ; E.Pinilla ; 'M.Rosario Torres' # Attachment 'comp3.CIF' data_comp3 _database_code_depnum_ccdc_archive 'CCDC 690489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N2 O4' _chemical_formula_weight 364.39 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 8.2394(10) _cell_length_b 14.0198(17) _cell_length_c 16.306(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.060(3) _cell_angle_gamma 90.00 _cell_volume 1848.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.092 _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 296(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 '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 13998 _diffrn_reflns_av_R_equivalents 0.1198 _diffrn_reflns_av_sigmaI/netI 0.1133 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3244 _reflns_number_gt 1418 _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^)+(0.0850P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3244 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1808 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7981(4) -0.0874(2) 0.47765(16) 0.0414(8) Uani 1 1 d . . . H1B H 0.8479 -0.1418 0.4448 0.050 Uiso 1 1 d R . . O1 O 0.2658(4) 0.20706(18) 0.92513(16) 0.0669(9) Uani 1 1 d . . . H1A H 0.2216 0.2859 0.9152 0.080 Uiso 1 1 d R . . N2 N 0.7324(4) -0.0950(2) 0.54736(17) 0.0413(8) Uani 1 1 d . . . O2 O 0.3461(3) 0.02550(17) 0.91249(15) 0.0554(8) Uani 1 1 d . . . C3 C 0.6912(4) -0.0054(2) 0.5651(2) 0.0381(9) Uani 1 1 d . . . O3 O 1.0726(4) 0.22812(17) 0.04960(15) 0.0647(9) Uani 1 1 d . . . H3 H 1.1467 0.1670 0.0348 0.078 Uiso 1 1 d R . . C4 C 0.7317(4) 0.0578(3) 0.5058(2) 0.0418(10) Uani 1 1 d . . . H4 H 0.7165 0.1236 0.5042 0.050 Uiso 1 1 calc R . . O4 O 1.1251(4) 0.04887(17) 0.09858(16) 0.0624(8) Uani 1 1 d . . . C5 C 0.7984(4) 0.0037(2) 0.4503(2) 0.0380(9) Uani 1 1 d . . . C6 C 0.6151(4) 0.0128(3) 0.6364(2) 0.0434(10) Uani 1 1 d . . . H6 H 0.6021 -0.0383 0.6709 0.052 Uiso 1 1 calc R . . C7 C 0.5626(5) 0.0978(3) 0.6556(2) 0.0467(10) Uani 1 1 d . . . H7 H 0.5788 0.1475 0.6203 0.056 Uiso 1 1 calc R . . C8 C 0.4822(5) 0.1239(2) 0.7253(2) 0.0424(10) Uani 1 1 d . . . C9 C 0.4524(4) 0.0579(3) 0.7855(2) 0.0424(10) Uani 1 1 d . . . H9 H 0.4819 -0.0056 0.7808 0.051 Uiso 1 1 calc R . . C10 C 0.3806(5) 0.0854(3) 0.8512(2) 0.0426(10) Uani 1 1 d . . . C11 C 0.3336(5) 0.1804(3) 0.8584(2) 0.0494(11) Uani 1 1 d . . . C12 C 0.3579(5) 0.2438(3) 0.7981(2) 0.0632(13) Uani 1 1 d . . . H12 H 0.3244 0.3068 0.8015 0.076 Uiso 1 1 calc R . . C13 C 0.4311(5) 0.2167(3) 0.7325(2) 0.0560(12) Uani 1 1 d . . . H13 H 0.4461 0.2615 0.6926 0.067 Uiso 1 1 calc R . . C14 C 0.4053(5) -0.0706(3) 0.9126(2) 0.0584(12) Uani 1 1 d . . . H14A H 0.3806 -0.1039 0.9602 0.088 Uiso 1 1 calc R . . H14B H 0.5227 -0.0701 0.9153 0.088 Uiso 1 1 calc R . . H14C H 0.3522 -0.1022 0.8623 0.088 Uiso 1 1 calc R . . C15 C 0.8598(4) 0.0265(3) 0.3750(2) 0.0419(10) Uani 1 1 d . . . H15 H 0.8978 -0.0237 0.3466 0.050 Uiso 1 1 calc R . . C16 C 0.8657(5) 0.1131(3) 0.3438(2) 0.0486(11) Uani 1 1 d . . . H16 H 0.8289 0.1624 0.3738 0.058 Uiso 1 1 calc R . . C17 C 0.9234(5) 0.1407(3) 0.2678(2) 0.0449(10) Uani 1 1 d . . . C18 C 0.9990(5) 0.0758(3) 0.2218(2) 0.0449(10) Uani 1 1 d . . . H18 H 1.0158 0.0132 0.2401 0.054 Uiso 1 1 calc R . . C19 C 1.0490(5) 0.1043(2) 0.1489(2) 0.0453(10) Uani 1 1 d . . . C20 C 1.0240(5) 0.1986(3) 0.1221(2) 0.0488(11) Uani 1 1 d . . . C21 C 0.9488(5) 0.2616(3) 0.1662(2) 0.0564(12) Uani 1 1 d . . . H21 H 0.9301 0.3240 0.1473 0.068 Uiso 1 1 calc R . . C22 C 0.8999(5) 0.2335(3) 0.2391(2) 0.0535(11) Uani 1 1 d . . . H22 H 0.8506 0.2775 0.2692 0.064 Uiso 1 1 calc R . . C23 C 1.1206(6) -0.0513(3) 0.1090(3) 0.0625(12) Uani 1 1 d . . . H23A H 1.1782 -0.0817 0.0702 0.094 Uiso 1 1 calc R . . H23B H 1.0077 -0.0725 0.0988 0.094 Uiso 1 1 calc R . . H23C H 1.1727 -0.0677 0.1650 0.094 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 N1 0.059(2) 0.0384(18) 0.0335(17) 0.0009(14) 0.0263(16) 0.0018(15) O1 0.106(2) 0.0453(16) 0.0652(18) -0.0067(14) 0.0550(18) 0.0070(16) N2 0.053(2) 0.0396(19) 0.0363(18) -0.0004(14) 0.0220(16) -0.0006(15) O2 0.084(2) 0.0438(16) 0.0466(16) 0.0002(13) 0.0321(15) 0.0025(14) C3 0.046(2) 0.039(2) 0.031(2) -0.0056(17) 0.0125(19) 0.0003(18) O3 0.109(2) 0.0405(16) 0.0570(18) 0.0091(13) 0.0460(17) -0.0046(15) C4 0.053(3) 0.037(2) 0.040(2) 0.0012(18) 0.019(2) -0.0007(18) O4 0.096(2) 0.0406(16) 0.0633(18) 0.0035(14) 0.0473(17) 0.0053(15) C5 0.039(2) 0.041(2) 0.037(2) 0.0013(18) 0.0124(18) -0.0021(17) C6 0.052(3) 0.042(2) 0.040(2) 0.0013(18) 0.020(2) -0.0001(19) C7 0.059(3) 0.046(2) 0.041(2) -0.0017(19) 0.025(2) -0.003(2) C8 0.050(3) 0.039(2) 0.042(2) -0.0050(18) 0.020(2) -0.0030(19) C9 0.050(3) 0.040(2) 0.041(2) -0.0084(18) 0.019(2) -0.0014(18) C10 0.050(3) 0.044(2) 0.037(2) -0.0013(18) 0.016(2) -0.0037(19) C11 0.067(3) 0.042(2) 0.049(2) -0.0093(19) 0.034(2) 0.000(2) C12 0.097(4) 0.039(2) 0.067(3) -0.002(2) 0.048(3) 0.009(2) C13 0.083(3) 0.042(2) 0.051(3) 0.003(2) 0.033(2) 0.005(2) C14 0.074(3) 0.046(3) 0.058(3) 0.003(2) 0.019(2) 0.000(2) C15 0.049(2) 0.044(2) 0.037(2) 0.0009(18) 0.019(2) 0.0007(19) C16 0.065(3) 0.043(2) 0.042(2) -0.0035(19) 0.022(2) 0.001(2) C17 0.062(3) 0.039(2) 0.037(2) 0.0023(18) 0.019(2) -0.003(2) C18 0.059(3) 0.033(2) 0.046(2) 0.0074(18) 0.019(2) -0.0010(18) C19 0.062(3) 0.037(2) 0.042(2) 0.0009(18) 0.024(2) -0.0005(19) C20 0.067(3) 0.040(2) 0.045(2) 0.0035(19) 0.026(2) -0.007(2) C21 0.083(3) 0.034(2) 0.059(3) 0.004(2) 0.030(3) -0.006(2) C22 0.075(3) 0.040(2) 0.052(3) -0.002(2) 0.030(2) 0.002(2) C23 0.085(3) 0.041(2) 0.069(3) -0.005(2) 0.032(3) 0.003(2) _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 N1 N2 1.354(3) . ? N1 C5 1.353(4) . ? N1 H1B 1.0584 . ? O1 C11 1.368(4) . ? O1 H1A 1.1654 . ? N2 C3 1.347(4) . ? O2 C10 1.376(4) . ? O2 C14 1.433(4) . ? C3 C4 1.399(4) . ? C3 C6 1.445(4) . ? O3 C20 1.382(4) . ? O3 H3 1.1049 . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? O4 C19 1.366(4) . ? O4 C23 1.416(4) . ? C5 C15 1.450(4) . ? C6 C7 1.327(4) . ? C6 H6 0.9300 . ? C7 C8 1.467(4) . ? C7 H7 0.9300 . ? C8 C13 1.379(5) . ? C8 C9 1.404(4) . ? C9 C10 1.374(4) . ? C9 H9 0.9300 . ? C10 C11 1.399(5) . ? C11 C12 1.368(5) . ? C12 C13 1.378(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.322(4) . ? C15 H15 0.9300 . ? C16 C17 1.463(5) . ? C16 H16 0.9300 . ? C17 C18 1.399(5) . ? C17 C22 1.383(5) . ? C18 C19 1.390(4) . ? C18 H18 0.9300 . ? C19 C20 1.396(5) . ? C20 C21 1.361(5) . ? C21 C22 1.383(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 112.2(3) . . ? N2 N1 H1B 128.6 . . ? C5 N1 H1B 119.3 . . ? C11 O1 H1A 108.2 . . ? C3 N2 N1 105.3(3) . . ? C10 O2 C14 117.2(3) . . ? N2 C3 C4 109.8(3) . . ? N2 C3 C6 120.2(3) . . ? C4 C3 C6 129.9(3) . . ? C20 O3 H3 102.6 . . ? C5 C4 C3 106.5(3) . . ? C5 C4 H4 126.7 . . ? C3 C4 H4 126.7 . . ? C19 O4 C23 117.8(3) . . ? N1 C5 C4 106.2(3) . . ? N1 C5 C15 120.6(3) . . ? C4 C5 C15 133.2(3) . . ? C7 C6 C3 124.1(3) . . ? C7 C6 H6 117.9 . . ? C3 C6 H6 117.9 . . ? C6 C7 C8 128.6(3) . . ? C6 C7 H7 115.7 . . ? C8 C7 H7 115.7 . . ? C13 C8 C9 117.7(3) . . ? C13 C8 C7 119.4(3) . . ? C9 C8 C7 122.9(3) . . ? C10 C9 C8 121.3(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 O2 125.1(3) . . ? C9 C10 C11 119.9(3) . . ? O2 C10 C11 114.9(3) . . ? O1 C11 C12 122.2(3) . . ? O1 C11 C10 119.3(3) . . ? C12 C11 C10 118.6(3) . . ? C13 C12 C11 121.6(4) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C8 120.8(4) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C5 124.9(3) . . ? C16 C15 H15 117.5 . . ? C5 C15 H15 117.5 . . ? C15 C16 C17 127.7(3) . . ? C15 C16 H16 116.1 . . ? C17 C16 H16 116.1 . . ? C18 C17 C22 118.6(3) . . ? C18 C17 C16 122.2(3) . . ? C22 C17 C16 119.2(3) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 O4 126.6(3) . . ? C18 C19 C20 119.3(3) . . ? O4 C19 C20 114.1(3) . . ? O3 C20 C21 119.6(3) . . ? O3 C20 C19 120.1(3) . . ? C21 C20 C19 120.3(3) . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.9(3) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C5 N1 N2 C3 -0.6(4) . . . . ? N1 N2 C3 C4 0.1(4) . . . . ? N1 N2 C3 C6 179.4(3) . . . . ? N2 C3 C4 C5 0.5(4) . . . . ? C6 C3 C4 C5 -178.8(4) . . . . ? N2 N1 C5 C4 0.9(4) . . . . ? N2 N1 C5 C15 -178.3(3) . . . . ? C3 C4 C5 N1 -0.8(4) . . . . ? C3 C4 C5 C15 178.3(4) . . . . ? N2 C3 C6 C7 -176.2(4) . . . . ? C4 C3 C6 C7 3.0(6) . . . . ? C3 C6 C7 C8 179.1(4) . . . . ? C6 C7 C8 C13 -177.6(4) . . . . ? C6 C7 C8 C9 1.7(6) . . . . ? C13 C8 C9 C10 -2.4(6) . . . . ? C7 C8 C9 C10 178.3(4) . . . . ? C8 C9 C10 O2 179.5(3) . . . . ? C8 C9 C10 C11 0.9(6) . . . . ? C14 O2 C10 C9 6.9(5) . . . . ? C14 O2 C10 C11 -174.4(3) . . . . ? C9 C10 C11 O1 -178.5(3) . . . . ? O2 C10 C11 O1 2.7(5) . . . . ? C9 C10 C11 C12 1.2(6) . . . . ? O2 C10 C11 C12 -177.6(4) . . . . ? O1 C11 C12 C13 178.0(4) . . . . ? C10 C11 C12 C13 -1.7(6) . . . . ? C11 C12 C13 C8 0.1(7) . . . . ? C9 C8 C13 C12 1.9(6) . . . . ? C7 C8 C13 C12 -178.8(4) . . . . ? N1 C5 C15 C16 -179.6(4) . . . . ? C4 C5 C15 C16 1.4(7) . . . . ? C5 C15 C16 C17 -178.9(4) . . . . ? C15 C16 C17 C18 -7.2(7) . . . . ? C15 C16 C17 C22 171.5(4) . . . . ? C22 C17 C18 C19 0.0(6) . . . . ? C16 C17 C18 C19 178.6(4) . . . . ? C17 C18 C19 O4 179.4(4) . . . . ? C17 C18 C19 C20 0.4(6) . . . . ? C23 O4 C19 C18 15.6(6) . . . . ? C23 O4 C19 C20 -165.3(4) . . . . ? C18 C19 C20 O3 -179.8(3) . . . . ? O4 C19 C20 O3 1.0(5) . . . . ? C18 C19 C20 C21 -1.1(6) . . . . ? O4 C19 C20 C21 179.8(4) . . . . ? O3 C20 C21 C22 -179.7(4) . . . . ? C19 C20 C21 C22 1.5(6) . . . . ? C20 C21 C22 C17 -1.2(6) . . . . ? C18 C17 C22 C21 0.5(6) . . . . ? C16 C17 C22 C21 -178.3(4) . . . . ? 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 O3 H3 O4 1.10 1.98 2.647(4) 115.1 . N1 H1B O3 1.06 1.93 2.864(4) 144.7 2_745 O1 H1A N2 1.17 1.79 2.811(4) 142.7 2_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.232 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.058 # Attachment 'comp4.CIF' data_comp4 _database_code_depnum_ccdc_archive 'CCDC 690490' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O2' _chemical_formula_weight 230.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.2563(15) _cell_length_b 7.6962(9) _cell_length_c 22.855(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2331.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.090 _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 296(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 '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 19397 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2541 _reflns_number_gt 1248 _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^)+(0.0840P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2541 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1252 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.052 _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 0.57529(15) 1.1620(2) 0.68737(7) 0.0508(6) Uani 1 1 d . . . H1A H 0.5186 1.2434 0.6804 0.061 Uiso 1 1 d R . . N1 N 0.58996(17) 0.4565(3) 0.31981(9) 0.0435(6) Uani 1 1 d . . . H1B H 0.5670 0.4739 0.2751 0.052 Uiso 1 1 d R . . O2 O 0.62105(16) 0.8377(2) 0.71175(7) 0.0541(6) Uani 1 1 d . . . N2 N 0.57923(17) 0.6090(3) 0.34970(9) 0.0473(6) Uani 1 1 d . . . C3 C 0.61222(19) 0.5728(3) 0.40372(11) 0.0402(6) Uani 1 1 d . . . C4 C 0.6432(2) 0.3996(4) 0.40733(11) 0.0463(7) Uani 1 1 d . . . H4 H 0.6688 0.3433 0.4401 0.056 Uiso 1 1 calc R . . C5 C 0.6283(2) 0.3291(3) 0.35302(11) 0.0410(6) Uani 1 1 d . . . C6 C 0.6142(2) 0.7087(3) 0.44782(11) 0.0445(7) Uani 1 1 d . . . H6 H 0.5993 0.8211 0.4356 0.053 Uiso 1 1 calc R . . C7 C 0.6354(2) 0.6865(4) 0.50398(11) 0.0459(7) Uani 1 1 d . . . H7 H 0.6548 0.5754 0.5153 0.055 Uiso 1 1 calc R . . C8 C 0.63139(19) 0.8194(3) 0.55023(11) 0.0403(6) Uani 1 1 d . . . C9 C 0.6369(2) 0.7664(3) 0.60830(11) 0.0450(7) Uani 1 1 d . . . H9 H 0.6519 0.6511 0.6168 0.054 Uiso 1 1 calc R . . C10 C 0.6206(2) 0.8817(3) 0.65378(11) 0.0409(7) Uani 1 1 d . . . C11 C 0.59883(19) 1.0551(3) 0.64150(11) 0.0399(7) Uani 1 1 d . . . C12 C 0.6027(2) 1.1112(4) 0.58400(11) 0.0447(7) Uani 1 1 d . . . H12 H 0.5950 1.2288 0.5757 0.054 Uiso 1 1 calc R . . C13 C 0.6177(2) 0.9953(4) 0.53890(11) 0.0476(7) Uani 1 1 d . . . H13 H 0.6187 1.0351 0.5005 0.057 Uiso 1 1 calc R . . C14 C 0.6586(2) 0.6710(3) 0.72680(11) 0.0525(8) Uani 1 1 d . . . H14A H 0.6579 0.6578 0.7686 0.079 Uiso 1 1 calc R . . H14B H 0.7264 0.6591 0.7127 0.079 Uiso 1 1 calc R . . H14C H 0.6168 0.5833 0.7093 0.079 Uiso 1 1 calc R . . C15 C 0.6459(2) 0.1525(3) 0.32900(13) 0.0549(8) Uani 1 1 d . . . H15A H 0.6075 0.1380 0.2937 0.082 Uiso 1 1 calc R . . H15B H 0.6254 0.0671 0.3572 0.082 Uiso 1 1 calc R . . H15C H 0.7164 0.1382 0.3205 0.082 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 0.0653(14) 0.0499(11) 0.0373(11) -0.0100(9) -0.0075(9) 0.0144(10) N1 0.0567(16) 0.0430(13) 0.0309(12) -0.0036(10) -0.0012(10) 0.0082(11) O2 0.0837(16) 0.0510(12) 0.0276(10) 0.0023(8) -0.0032(10) 0.0170(10) N2 0.0665(17) 0.0436(13) 0.0318(12) -0.0019(10) -0.0056(11) 0.0106(11) C3 0.0455(16) 0.0443(15) 0.0308(14) -0.0008(11) -0.0003(11) 0.0043(13) C4 0.0563(19) 0.0477(17) 0.0350(15) 0.0052(12) -0.0050(13) 0.0062(14) C5 0.0439(16) 0.0401(14) 0.0389(15) 0.0001(12) 0.0019(13) 0.0004(12) C6 0.0548(18) 0.0458(16) 0.0330(15) -0.0026(12) 0.0008(13) 0.0078(13) C7 0.0552(19) 0.0499(16) 0.0325(15) -0.0010(12) -0.0009(13) 0.0057(13) C8 0.0435(16) 0.0471(16) 0.0302(14) -0.0012(11) -0.0021(12) 0.0017(12) C9 0.0551(19) 0.0442(16) 0.0357(15) -0.0004(12) -0.0029(13) 0.0072(13) C10 0.0514(17) 0.0447(15) 0.0266(14) 0.0012(11) -0.0036(12) 0.0051(13) C11 0.0426(16) 0.0420(15) 0.0352(14) -0.0053(12) -0.0063(12) 0.0019(12) C12 0.0537(18) 0.0407(15) 0.0398(16) 0.0002(12) -0.0015(13) -0.0045(13) C13 0.0576(19) 0.0519(17) 0.0334(15) 0.0045(12) -0.0002(13) -0.0032(14) C14 0.071(2) 0.0477(17) 0.0385(16) 0.0074(13) -0.0058(14) 0.0082(15) C15 0.059(2) 0.0460(17) 0.059(2) -0.0068(14) 0.0013(15) 0.0003(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 O1 C11 1.369(3) . ? O1 H1A 0.9912 . ? N1 C5 1.340(3) . ? N1 N2 1.365(3) . ? N1 H1B 1.0737 . ? O2 C10 1.367(3) . ? O2 C14 1.419(3) . ? N2 C3 1.339(3) . ? C3 C4 1.398(4) . ? C3 C6 1.453(3) . ? C4 C5 1.369(4) . ? C4 H4 0.9300 . ? C5 C15 1.484(4) . ? C6 C7 1.325(3) . ? C6 H6 0.9300 . ? C7 C8 1.472(4) . ? C7 H7 0.9300 . ? C8 C9 1.390(4) . ? C8 C13 1.390(4) . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 C11 1.394(4) . ? C11 C12 1.384(4) . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 H1A 115.4 . . ? C5 N1 N2 112.7(2) . . ? C5 N1 H1B 137.5 . . ? N2 N1 H1B 109.9 . . ? C10 O2 C14 117.4(2) . . ? C3 N2 N1 104.4(2) . . ? N2 C3 C4 110.4(2) . . ? N2 C3 C6 119.7(2) . . ? C4 C3 C6 129.8(2) . . ? C5 C4 C3 106.4(2) . . ? C5 C4 H4 126.8 . . ? C3 C4 H4 126.8 . . ? N1 C5 C4 106.1(2) . . ? N1 C5 C15 121.4(2) . . ? C4 C5 C15 132.5(3) . . ? C7 C6 C3 125.7(2) . . ? C7 C6 H6 117.2 . . ? C3 C6 H6 117.2 . . ? C6 C7 C8 126.8(3) . . ? C6 C7 H7 116.6 . . ? C8 C7 H7 116.6 . . ? C9 C8 C13 118.0(2) . . ? C9 C8 C7 118.7(2) . . ? C13 C8 C7 123.2(2) . . ? C8 C9 C10 121.4(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? O2 C10 C11 115.6(2) . . ? O2 C10 C9 124.7(2) . . ? C11 C10 C9 119.7(2) . . ? C12 C11 C10 118.8(2) . . ? C12 C11 O1 123.2(2) . . ? C10 C11 O1 118.0(2) . . ? C11 C12 C13 120.9(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 120.7(2) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C5 N1 N2 C3 -0.2(3) . . . . ? N1 N2 C3 C4 0.0(3) . . . . ? N1 N2 C3 C6 178.4(2) . . . . ? N2 C3 C4 C5 0.1(3) . . . . ? C6 C3 C4 C5 -178.0(3) . . . . ? N2 N1 C5 C4 0.3(3) . . . . ? N2 N1 C5 C15 179.9(2) . . . . ? C3 C4 C5 N1 -0.3(3) . . . . ? C3 C4 C5 C15 -179.8(3) . . . . ? N2 C3 C6 C7 172.9(3) . . . . ? C4 C3 C6 C7 -9.1(5) . . . . ? C3 C6 C7 C8 -175.6(3) . . . . ? C6 C7 C8 C9 167.6(3) . . . . ? C6 C7 C8 C13 -9.3(5) . . . . ? C13 C8 C9 C10 5.6(4) . . . . ? C7 C8 C9 C10 -171.6(3) . . . . ? C14 O2 C10 C11 -170.0(2) . . . . ? C14 O2 C10 C9 12.0(4) . . . . ? C8 C9 C10 O2 177.5(3) . . . . ? C8 C9 C10 C11 -0.5(4) . . . . ? O2 C10 C11 C12 176.4(2) . . . . ? C9 C10 C11 C12 -5.5(4) . . . . ? O2 C10 C11 O1 -3.2(3) . . . . ? C9 C10 C11 O1 174.9(2) . . . . ? C10 C11 C12 C13 6.4(4) . . . . ? O1 C11 C12 C13 -174.0(3) . . . . ? C11 C12 C13 C8 -1.3(4) . . . . ? C9 C8 C13 C12 -4.7(4) . . . . ? C7 C8 C13 C12 172.3(3) . . . . ? 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 O1 H1A N2 0.99 1.86 2.832(3) 167.5 5_676 N1 H1B O2 1.07 2.17 2.962(3) 128.6 7_575 N1 H1B O1 1.07 2.26 3.167(3) 140.5 7_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.214 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.047 # Attachment 'comp5.CIF' data_comp5 _database_code_depnum_ccdc_archive 'CCDC 690491' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O2' _chemical_formula_weight 244.29 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 8.519(2) _cell_length_b 12.964(4) _cell_length_c 34.615(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.607(7) _cell_angle_gamma 90.00 _cell_volume 3810.6(19) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.087 _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 296(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 '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 28784 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6720 _reflns_number_gt 2855 _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^)+(0.1271P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0064(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6720 _refine_ls_number_parameters 497 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1710 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.2486 _refine_ls_wR_factor_gt 0.1960 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.038 _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 O11 O 2.1618(4) -0.4134(2) 0.84305(9) 0.0671(10) Uani 1 1 d . . . H111 H 2.2567 -0.3870 0.8534 0.081 Uiso 1 1 d R . . N11 N 1.6884(4) -0.1150(3) 0.63903(10) 0.0598(11) Uani 1 1 d . . . H11 H 1.7428 -0.0550 0.6571 0.072 Uiso 1 1 d R . . N21 N 1.5955(4) -0.0979(3) 0.60623(10) 0.0557(11) Uani 1 1 d . . . O21 O 2.1984(4) -0.2122(3) 0.82821(11) 0.0778(11) Uani 1 1 d . . . C31 C 1.5335(5) -0.1906(4) 0.59689(12) 0.0528(12) Uani 1 1 d . . . C41 C 1.5880(6) -0.2659(4) 0.62311(13) 0.0591(13) Uani 1 1 d . . . C51 C 1.6878(6) -0.2136(4) 0.64977(14) 0.0641(14) Uani 1 1 d . . . C61 C 1.7649(7) -0.2644(6) 0.68333(17) 0.106(2) Uani 1 1 d D . . H61 H 1.7567 -0.3359 0.6837 0.127 Uiso 1 1 calc R . . C71 C 1.8449(7) -0.2229(5) 0.71328(14) 0.105(2) Uani 1 1 d D . . H71A H 1.8563 -0.1515 0.7133 0.126 Uiso 1 1 calc R . . C81 C 1.9175(7) -0.2791(6) 0.74662(15) 0.0828(19) Uani 1 1 d D . . C91 C 2.0161(7) -0.2236(5) 0.77086(15) 0.0794(17) Uani 1 1 d . . . H91 H 2.0291 -0.1539 0.7657 0.095 Uiso 1 1 calc R . . C101 C 2.0985(6) -0.2653(4) 0.80291(14) 0.0609(13) Uani 1 1 d . . . C111 C 2.0811(6) -0.3692(4) 0.81137(12) 0.0575(13) Uani 1 1 d . . . C121 C 1.9787(6) -0.4288(4) 0.78823(14) 0.0728(16) Uani 1 1 d . . . H121 H 1.9634 -0.4981 0.7939 0.087 Uiso 1 1 calc R . . C131 C 1.8970(6) -0.3819(6) 0.75546(15) 0.0850(19) Uani 1 1 d . . . H131 H 1.8276 -0.4215 0.7395 0.102 Uiso 1 1 calc R . . C141 C 2.2140(7) -0.1036(4) 0.82344(19) 0.096(2) Uani 1 1 d . . . H14A H 2.2666 -0.0745 0.8465 0.144 Uiso 1 1 calc R . . H14B H 2.1115 -0.0732 0.8189 0.144 Uiso 1 1 calc R . . H14C H 2.2745 -0.0900 0.8018 0.144 Uiso 1 1 calc R . . C151 C 1.4225(6) -0.2050(4) 0.56201(13) 0.0719(16) Uani 1 1 d . . . H15A H 1.3821 -0.1392 0.5533 0.108 Uiso 1 1 calc R . . H15B H 1.3370 -0.2484 0.5684 0.108 Uiso 1 1 calc R . . H15C H 1.4768 -0.2367 0.5419 0.108 Uiso 1 1 calc R . . C161 C 1.5447(8) -0.3770(4) 0.62251(17) 0.097(2) Uani 1 1 d . . . H16A H 1.5232 -0.3985 0.6481 0.146 Uiso 1 1 calc R . . H16B H 1.6302 -0.4170 0.6140 0.146 Uiso 1 1 calc R . . H16C H 1.4525 -0.3873 0.6051 0.146 Uiso 1 1 calc R . . O12 O 0.1715(4) -0.0260(2) 0.17134(8) 0.0607(9) Uani 1 1 d . . . H112 H 0.1894 -0.1074 0.1598 0.073 Uiso 1 1 d R . . N12 N 0.9354(4) 0.2668(3) 0.38062(10) 0.0511(10) Uani 1 1 d . . . H12 H 0.9741 0.3419 0.3923 0.061 Uiso 1 1 d R . . N22 N 0.8392(4) 0.2741(3) 0.34771(10) 0.0518(10) Uani 1 1 d . . . O22 O 0.3071(4) 0.1560(2) 0.17190(8) 0.0638(10) Uani 1 1 d . . . C32 C 0.7808(5) 0.1784(3) 0.34145(12) 0.0448(11) Uani 1 1 d . . . C42 C 0.8419(5) 0.1107(3) 0.37080(12) 0.0457(11) Uani 1 1 d . . . C52 C 0.9394(5) 0.1701(3) 0.39491(12) 0.0478(12) Uani 1 1 d . . . C62 C 0.6713(5) 0.1606(3) 0.30731(12) 0.0539(13) Uani 1 1 d . . . H62 H 0.6549 0.2153 0.2901 0.065 Uiso 1 1 calc R . . C72 C 0.5941(5) 0.0752(4) 0.29858(12) 0.0546(13) Uani 1 1 d . . . H72 H 0.6130 0.0213 0.3161 0.065 Uiso 1 1 calc R . . C82 C 0.4832(5) 0.0524(3) 0.26545(12) 0.0476(11) Uani 1 1 d . . . C92 C 0.4499(5) 0.1214(3) 0.23481(11) 0.0502(12) Uani 1 1 d . . . H92 H 0.4981 0.1858 0.2355 0.060 Uiso 1 1 calc R . . C102 C 0.3461(5) 0.0950(3) 0.20342(11) 0.0452(11) Uani 1 1 d . . . C112 C 0.2724(5) -0.0010(3) 0.20239(12) 0.0487(12) Uani 1 1 d . . . C122 C 0.3013(5) -0.0681(3) 0.23327(12) 0.0536(12) Uani 1 1 d . . . H122 H 0.2497 -0.1313 0.2332 0.064 Uiso 1 1 calc R . . C132 C 0.4068(6) -0.0413(3) 0.26422(13) 0.0563(13) Uani 1 1 d . . . H132 H 0.4265 -0.0876 0.2846 0.068 Uiso 1 1 calc R . . C142 C 0.3698(7) 0.2583(3) 0.17278(14) 0.0706(15) Uani 1 1 d . . . H14D H 0.3361 0.2932 0.1491 0.106 Uiso 1 1 calc R . . H14E H 0.4827 0.2553 0.1756 0.106 Uiso 1 1 calc R . . H14F H 0.3326 0.2953 0.1943 0.106 Uiso 1 1 calc R . . C152 C 1.0375(6) 0.1433(4) 0.43110(12) 0.0654(14) Uani 1 1 d . . . H15D H 1.1401 0.1735 0.4304 0.098 Uiso 1 1 calc R . . H15E H 1.0473 0.0697 0.4331 0.098 Uiso 1 1 calc R . . H15F H 0.9883 0.1694 0.4531 0.098 Uiso 1 1 calc R . . C162 C 0.8082(6) 0.0001(3) 0.37769(14) 0.0674(15) Uani 1 1 d . . . H16D H 0.8570 -0.0203 0.4025 0.101 Uiso 1 1 calc R . . H16E H 0.8492 -0.0409 0.3577 0.101 Uiso 1 1 calc R . . H16F H 0.6964 -0.0099 0.3773 0.101 Uiso 1 1 calc R . . N13 N 0.9759(5) 0.5501(3) 0.39994(10) 0.0576(11) Uani 1 1 d . . . H13 H 0.9052 0.5485 0.3746 0.069 Uiso 1 1 d R . . O13 O 1.6011(4) 0.1151(2) 0.59654(9) 0.0724(11) Uani 1 1 d . . . H113 H 1.5517 0.0327 0.5900 0.087 Uiso 1 1 d R . . N23 N 1.0405(5) 0.4620(3) 0.41545(10) 0.0598(11) Uani 1 1 d . . . O23 O 1.3978(4) 0.0570(2) 0.53632(9) 0.0741(11) Uani 1 1 d . . . C33 C 1.1219(5) 0.4924(3) 0.44851(12) 0.0479(12) Uani 1 1 d . . . C43 C 1.1072(5) 0.5990(3) 0.45394(12) 0.0492(12) Uani 1 1 d . . . C53 C 1.0132(5) 0.6317(3) 0.42218(13) 0.0528(12) Uani 1 1 d . . . C63 C 1.2057(5) 0.4140(3) 0.47180(13) 0.0552(13) Uani 1 1 d . . . H63 H 1.2042 0.3482 0.4611 0.066 Uiso 1 1 calc R . . C73 C 1.2829(6) 0.4229(4) 0.50571(13) 0.0582(13) Uani 1 1 d . . . H73 H 1.2870 0.4886 0.5165 0.070 Uiso 1 1 calc R . . C83 C 1.3646(6) 0.3407(4) 0.52895(13) 0.0555(13) Uani 1 1 d . . . C93 C 1.3394(5) 0.2365(3) 0.52070(12) 0.0526(12) Uani 1 1 d . . . H93 H 1.2689 0.2177 0.5000 0.063 Uiso 1 1 calc R . . C103 C 1.4169(5) 0.1609(3) 0.54261(12) 0.0522(12) Uani 1 1 d . . . C113 C 1.5207(6) 0.1868(4) 0.57393(12) 0.0540(13) Uani 1 1 d . . . C123 C 1.5432(6) 0.2886(4) 0.58266(14) 0.0685(15) Uani 1 1 d . . . H123 H 1.6119 0.3070 0.6038 0.082 Uiso 1 1 calc R . . C133 C 1.4659(6) 0.3650(4) 0.56076(13) 0.0671(15) Uani 1 1 d . . . H133 H 1.4825 0.4337 0.5676 0.081 Uiso 1 1 calc R . . C143 C 1.2862(7) 0.0261(4) 0.50492(15) 0.088(2) Uani 1 1 d . . . H14G H 1.2896 -0.0475 0.5019 0.131 Uiso 1 1 calc R . . H14H H 1.3126 0.0585 0.4814 0.131 Uiso 1 1 calc R . . H14I H 1.1822 0.0466 0.5105 0.131 Uiso 1 1 calc R . . C153 C 0.9567(7) 0.7379(4) 0.40989(15) 0.0727(16) Uani 1 1 d . . . H15G H 1.0002 0.7880 0.4282 0.109 Uiso 1 1 calc R . . H15H H 0.8438 0.7402 0.4090 0.109 Uiso 1 1 calc R . . H15I H 0.9901 0.7532 0.3847 0.109 Uiso 1 1 calc R . . C163 C 1.1698(7) 0.6658(4) 0.48700(14) 0.0734(16) Uani 1 1 d . . . H16G H 1.1360 0.7357 0.4823 0.110 Uiso 1 1 calc R . . H16H H 1.2828 0.6631 0.4892 0.110 Uiso 1 1 calc R . . H16I H 1.1307 0.6415 0.5106 0.110 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 O11 0.072(2) 0.063(2) 0.061(2) 0.0101(16) -0.0267(18) -0.0013(18) N11 0.060(3) 0.071(3) 0.045(2) -0.005(2) -0.016(2) 0.009(2) N21 0.063(3) 0.052(2) 0.049(2) -0.0003(19) -0.012(2) 0.003(2) O21 0.079(3) 0.062(2) 0.089(3) 0.017(2) -0.016(2) -0.003(2) C31 0.053(3) 0.058(3) 0.046(3) -0.001(2) 0.000(2) 0.005(3) C41 0.068(3) 0.056(3) 0.053(3) 0.005(2) 0.001(3) 0.013(3) C51 0.061(3) 0.081(4) 0.049(3) 0.015(3) -0.005(3) 0.025(3) C61 0.089(5) 0.143(6) 0.083(5) -0.008(4) -0.003(4) 0.040(4) C71 0.089(5) 0.149(6) 0.076(4) -0.005(4) -0.002(4) 0.030(4) C81 0.076(4) 0.115(5) 0.057(4) 0.026(4) -0.004(3) 0.038(4) C91 0.073(4) 0.103(5) 0.061(3) 0.027(3) -0.004(3) 0.029(4) C101 0.061(3) 0.072(4) 0.049(3) 0.009(3) 0.000(3) 0.015(3) C111 0.067(3) 0.060(3) 0.043(3) 0.006(2) -0.009(2) 0.016(3) C121 0.070(4) 0.081(4) 0.064(3) -0.018(3) -0.014(3) 0.008(3) C131 0.060(4) 0.137(6) 0.053(3) -0.034(4) -0.021(3) 0.019(4) C141 0.103(5) 0.057(4) 0.130(5) 0.017(3) 0.019(4) 0.008(3) C151 0.078(4) 0.088(4) 0.047(3) -0.006(3) -0.012(3) -0.010(3) C161 0.128(6) 0.054(4) 0.109(5) 0.009(3) 0.003(4) 0.009(4) O12 0.078(2) 0.0470(18) 0.0507(18) -0.0068(15) -0.0321(17) -0.0007(16) N12 0.055(2) 0.043(2) 0.053(2) -0.0045(18) -0.013(2) -0.0020(18) N22 0.058(2) 0.047(2) 0.047(2) -0.0021(18) -0.018(2) -0.0050(19) O22 0.091(3) 0.0469(19) 0.0493(18) 0.0073(15) -0.0226(17) -0.0104(18) C32 0.048(3) 0.043(3) 0.041(2) -0.005(2) -0.012(2) 0.000(2) C42 0.047(3) 0.043(3) 0.046(2) -0.001(2) -0.006(2) 0.002(2) C52 0.054(3) 0.042(3) 0.045(3) 0.000(2) -0.011(2) 0.002(2) C62 0.066(3) 0.046(3) 0.046(3) 0.002(2) -0.016(2) 0.002(2) C72 0.062(3) 0.049(3) 0.049(3) -0.002(2) -0.016(2) 0.001(2) C82 0.049(3) 0.043(3) 0.048(3) -0.001(2) -0.013(2) 0.002(2) C92 0.055(3) 0.044(3) 0.049(3) -0.005(2) -0.010(2) -0.006(2) C102 0.051(3) 0.044(3) 0.039(2) 0.001(2) -0.005(2) 0.004(2) C112 0.053(3) 0.043(3) 0.047(3) -0.006(2) -0.019(2) 0.000(2) C122 0.064(3) 0.042(3) 0.051(3) -0.002(2) -0.015(2) -0.005(2) C132 0.066(3) 0.048(3) 0.051(3) 0.003(2) -0.016(2) -0.001(3) C142 0.095(4) 0.046(3) 0.068(3) 0.008(2) -0.011(3) -0.008(3) C152 0.072(4) 0.067(3) 0.053(3) 0.002(2) -0.023(3) 0.003(3) C162 0.087(4) 0.047(3) 0.065(3) 0.002(2) -0.014(3) 0.000(3) N13 0.069(3) 0.052(2) 0.048(2) -0.001(2) -0.016(2) 0.001(2) O13 0.086(3) 0.058(2) 0.067(2) 0.0086(17) -0.0358(19) -0.0038(18) N23 0.076(3) 0.049(2) 0.050(2) 0.0003(19) -0.021(2) -0.002(2) O23 0.099(3) 0.052(2) 0.064(2) 0.0031(17) -0.0413(19) 0.0044(19) C33 0.054(3) 0.046(3) 0.042(3) 0.001(2) -0.008(2) -0.005(2) C43 0.056(3) 0.047(3) 0.043(3) -0.003(2) -0.007(2) -0.002(2) C53 0.059(3) 0.047(3) 0.052(3) 0.000(2) -0.003(2) 0.003(2) C63 0.064(3) 0.043(3) 0.055(3) 0.002(2) -0.012(3) 0.002(2) C73 0.071(3) 0.049(3) 0.052(3) 0.001(2) -0.014(3) 0.000(2) C83 0.061(3) 0.054(3) 0.050(3) 0.001(2) -0.004(2) 0.000(2) C93 0.061(3) 0.052(3) 0.042(3) 0.001(2) -0.015(2) 0.004(2) C103 0.058(3) 0.053(3) 0.042(3) 0.001(2) -0.012(2) -0.001(2) C113 0.062(3) 0.052(3) 0.045(3) 0.006(2) -0.013(2) -0.001(2) C123 0.083(4) 0.066(4) 0.050(3) 0.003(3) -0.026(3) -0.007(3) C133 0.089(4) 0.057(3) 0.051(3) 0.000(2) -0.025(3) -0.006(3) C143 0.114(5) 0.063(3) 0.076(4) -0.004(3) -0.051(4) -0.008(3) C153 0.088(4) 0.055(3) 0.073(3) 0.007(3) -0.008(3) 0.012(3) C163 0.097(4) 0.057(3) 0.063(3) -0.009(3) -0.014(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C111 1.372(5) . ? O11 H111 0.9239 . ? N11 C51 1.332(6) . ? N11 N21 1.349(4) . ? N11 H11 1.0784 . ? N21 C31 1.341(5) . ? O21 C101 1.359(6) . ? O21 C141 1.424(6) . ? C31 C41 1.388(6) . ? C31 C151 1.484(6) . ? C41 C51 1.381(6) . ? C41 C161 1.488(7) . ? C51 C61 1.446(7) . ? C61 C71 1.3093(6) . ? C61 H61 0.9300 . ? C71 C81 1.4602(6) . ? C71 H71A 0.9300 . ? C81 C91 1.347(8) . ? C81 C131 1.381(8) . ? C91 C101 1.375(6) . ? C91 H91 0.9300 . ? C101 C111 1.389(7) . ? C111 C121 1.374(6) . ? C121 C131 1.420(7) . ? C121 H121 0.9300 . ? C131 H131 0.9300 . ? C141 H14A 0.9600 . ? C141 H14B 0.9600 . ? C141 H14C 0.9600 . ? C151 H15A 0.9600 . ? C151 H15B 0.9600 . ? C151 H15C 0.9600 . ? C161 H16A 0.9600 . ? C161 H16B 0.9600 . ? C161 H16C 0.9600 . ? O12 C112 1.361(5) . ? O12 H112 1.1424 . ? N12 C52 1.346(5) . ? N12 N22 1.352(4) . ? N12 H12 1.0959 . ? N22 C32 1.348(5) . ? O22 C102 1.367(4) . ? O22 C142 1.430(5) . ? C32 C42 1.410(5) . ? C32 C62 1.463(5) . ? C42 C52 1.366(5) . ? C42 C162 1.486(6) . ? C52 C152 1.490(5) . ? C62 C72 1.310(6) . ? C62 H62 0.9300 . ? C72 C82 1.457(5) . ? C72 H72 0.9300 . ? C82 C92 1.399(5) . ? C82 C132 1.376(6) . ? C92 C102 1.388(5) . ? C92 H92 0.9300 . ? C102 C112 1.392(6) . ? C112 C122 1.385(6) . ? C122 C132 1.387(6) . ? C122 H122 0.9300 . ? C132 H132 0.9300 . ? C142 H14D 0.9600 . ? C142 H14E 0.9600 . ? C142 H14F 0.9600 . ? C152 H15D 0.9600 . ? C152 H15E 0.9600 . ? C152 H15F 0.9600 . ? C162 H16D 0.9600 . ? C162 H16E 0.9600 . ? C162 H16F 0.9600 . ? N13 N23 1.359(5) . ? N13 C53 1.331(5) . ? N13 H13 1.0225 . ? O13 C113 1.363(5) . ? O13 H113 1.1636 . ? N23 C33 1.349(5) . ? O23 C103 1.372(5) . ? O23 C143 1.442(5) . ? C33 C43 1.401(6) . ? C33 C63 1.450(6) . ? C43 C53 1.374(6) . ? C43 C163 1.499(6) . ? C53 C153 1.509(6) . ? C63 C73 1.304(6) . ? C63 H63 0.9300 . ? C73 C83 1.475(6) . ? C73 H73 0.9300 . ? C83 C93 1.394(6) . ? C83 C133 1.380(6) . ? C93 C103 1.375(6) . ? C93 H93 0.9300 . ? C103 C113 1.385(6) . ? C113 C123 1.365(6) . ? C123 C133 1.381(6) . ? C123 H123 0.9300 . ? C133 H133 0.9300 . ? C143 H14G 0.9600 . ? C143 H14H 0.9600 . ? C143 H14I 0.9600 . ? C153 H15G 0.9600 . ? C153 H15H 0.9600 . ? C153 H15I 0.9600 . ? C163 H16G 0.9600 . ? C163 H16H 0.9600 . ? C163 H16I 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C111 O11 H111 121.6 . . ? C51 N11 N21 112.2(4) . . ? C51 N11 H11 122.8 . . ? N21 N11 H11 124.4 . . ? C31 N21 N11 104.4(3) . . ? C101 O21 C141 119.1(4) . . ? N21 C31 C41 111.6(4) . . ? N21 C31 C151 121.4(4) . . ? C41 C31 C151 127.0(5) . . ? C51 C41 C31 104.4(4) . . ? C51 C41 C161 128.6(5) . . ? C31 C41 C161 127.1(5) . . ? N11 C51 C41 107.5(4) . . ? N11 C51 C61 130.5(5) . . ? C41 C51 C61 121.9(5) . . ? C71 C61 C51 128.5(6) . . ? C71 C61 H61 115.8 . . ? C51 C61 H61 115.8 . . ? C61 C71 C81 125.5(6) . . ? C61 C71 H71A 117.2 . . ? C81 C71 H71A 117.2 . . ? C91 C81 C131 117.5(4) . . ? C91 C81 C71 115.4(6) . . ? C131 C81 C71 127.1(6) . . ? C81 C91 C101 123.0(6) . . ? C81 C91 H91 118.5 . . ? C101 C91 H91 118.5 . . ? O21 C101 C111 115.3(4) . . ? O21 C101 C91 125.0(5) . . ? C111 C101 C91 119.7(5) . . ? C101 C111 O11 121.2(4) . . ? C101 C111 C121 119.7(4) . . ? O11 C111 C121 119.0(4) . . ? C111 C121 C131 118.2(5) . . ? C111 C121 H121 120.9 . . ? C131 C121 H121 120.9 . . ? C81 C131 C121 121.8(5) . . ? C81 C131 H131 119.1 . . ? C121 C131 H131 119.1 . . ? O21 C141 H14A 109.5 . . ? O21 C141 H14B 109.5 . . ? H14A C141 H14B 109.5 . . ? O21 C141 H14C 109.5 . . ? H14A C141 H14C 109.5 . . ? H14B C141 H14C 109.5 . . ? C31 C151 H15A 109.5 . . ? C31 C151 H15B 109.5 . . ? H15A C151 H15B 109.5 . . ? C31 C151 H15C 109.5 . . ? H15A C151 H15C 109.5 . . ? H15B C151 H15C 109.5 . . ? C41 C161 H16A 109.5 . . ? C41 C161 H16B 109.5 . . ? H16A C161 H16B 109.5 . . ? C41 C161 H16C 109.5 . . ? H16A C161 H16C 109.5 . . ? H16B C161 H16C 109.5 . . ? C112 O12 H112 113.7 . . ? C52 N12 N22 111.8(3) . . ? C52 N12 H12 133.9 . . ? N22 N12 H12 113.1 . . ? C32 N22 N12 105.2(3) . . ? C102 O22 C142 117.0(3) . . ? N22 C32 C42 110.3(3) . . ? N22 C32 C62 118.6(4) . . ? C42 C32 C62 131.1(4) . . ? C52 C42 C32 105.1(4) . . ? C52 C42 C162 124.2(4) . . ? C32 C42 C162 130.6(4) . . ? N12 C52 C42 107.7(3) . . ? N12 C52 C152 121.5(4) . . ? C42 C52 C152 130.9(4) . . ? C72 C62 C32 126.5(4) . . ? C72 C62 H62 116.7 . . ? C32 C62 H62 116.7 . . ? C62 C72 C82 129.4(4) . . ? C62 C72 H72 115.3 . . ? C82 C72 H72 115.3 . . ? C92 C82 C132 118.3(4) . . ? C92 C82 C72 123.1(4) . . ? C132 C82 C72 118.6(4) . . ? C82 C92 C102 120.9(4) . . ? C82 C92 H92 119.6 . . ? C102 C92 H92 119.6 . . ? C112 C102 O22 114.6(3) . . ? C112 C102 C92 119.9(4) . . ? O22 C102 C92 125.5(4) . . ? O12 C112 C102 119.2(4) . . ? O12 C112 C122 121.5(4) . . ? C102 C112 C122 119.3(4) . . ? C112 C122 C132 120.2(4) . . ? C112 C122 H122 119.9 . . ? C132 C122 H122 119.9 . . ? C122 C132 C82 121.4(4) . . ? C122 C132 H132 119.3 . . ? C82 C132 H132 119.3 . . ? O22 C142 H14D 109.5 . . ? O22 C142 H14E 109.5 . . ? H14D C142 H14E 109.5 . . ? O22 C142 H14F 109.5 . . ? H14D C142 H14F 109.5 . . ? H14E C142 H14F 109.5 . . ? C52 C152 H15D 109.5 . . ? C52 C152 H15E 109.5 . . ? H15D C152 H15E 109.5 . . ? C52 C152 H15F 109.5 . . ? H15D C152 H15F 109.5 . . ? H15E C152 H15F 109.5 . . ? C42 C162 H16D 109.5 . . ? C42 C162 H16E 109.5 . . ? H16D C162 H16E 109.5 . . ? C42 C162 H16F 109.5 . . ? H16D C162 H16F 109.5 . . ? H16E C162 H16F 109.5 . . ? N23 N13 C53 111.6(3) . . ? N23 N13 H13 120.9 . . ? C53 N13 H13 127.5 . . ? C113 O13 H113 110.9 . . ? C33 N23 N13 104.7(3) . . ? C103 O23 C143 117.0(3) . . ? N23 C33 C43 110.9(4) . . ? N23 C33 C63 117.6(4) . . ? C43 C33 C63 131.5(4) . . ? C53 C43 C33 104.5(4) . . ? C53 C43 C163 125.5(4) . . ? C33 C43 C163 130.0(4) . . ? C43 C53 N13 108.3(4) . . ? C43 C53 C153 131.3(4) . . ? N13 C53 C153 120.4(4) . . ? C73 C63 C33 129.0(4) . . ? C73 C63 H63 115.5 . . ? C33 C63 H63 115.5 . . ? C63 C73 C83 127.5(4) . . ? C63 C73 H73 116.2 . . ? C83 C73 H73 116.2 . . ? C93 C83 C133 117.4(4) . . ? C93 C83 C73 122.0(4) . . ? C133 C83 C73 120.5(4) . . ? C103 C93 C83 121.3(4) . . ? C103 C93 H93 119.4 . . ? C83 C93 H93 119.4 . . ? O23 C103 C113 115.0(4) . . ? O23 C103 C93 124.5(4) . . ? C113 C103 C93 120.5(4) . . ? O13 C113 C123 118.5(4) . . ? O13 C113 C103 123.0(4) . . ? C123 C113 C103 118.5(4) . . ? C113 C123 C133 121.3(4) . . ? C113 C123 H123 119.4 . . ? C133 C123 H123 119.4 . . ? C83 C133 C123 121.0(5) . . ? C83 C133 H133 119.5 . . ? C123 C133 H133 119.5 . . ? O23 C143 H14G 109.5 . . ? O23 C143 H14H 109.5 . . ? H14G C143 H14H 109.5 . . ? O23 C143 H14I 109.5 . . ? H14G C143 H14I 109.5 . . ? H14H C143 H14I 109.5 . . ? C53 C153 H15G 109.5 . . ? C53 C153 H15H 109.5 . . ? H15G C153 H15H 109.5 . . ? C53 C153 H15I 109.5 . . ? H15G C153 H15I 109.5 . . ? H15H C153 H15I 109.5 . . ? C43 C163 H16G 109.5 . . ? C43 C163 H16H 109.5 . . ? H16G C163 H16H 109.5 . . ? C43 C163 H16I 109.5 . . ? H16G C163 H16I 109.5 . . ? H16H C163 H16I 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 C51 N11 N21 C31 0.9(5) . . . . ? N11 N21 C31 C41 -0.8(5) . . . . ? N11 N21 C31 C151 180.0(4) . . . . ? N21 C31 C41 C51 0.5(6) . . . . ? C151 C31 C41 C51 179.6(5) . . . . ? N21 C31 C41 C161 179.4(5) . . . . ? C151 C31 C41 C161 -1.5(9) . . . . ? N21 N11 C51 C41 -0.6(6) . . . . ? N21 N11 C51 C61 -177.5(5) . . . . ? C31 C41 C51 N11 0.1(6) . . . . ? C161 C41 C51 N11 -178.8(5) . . . . ? C31 C41 C51 C61 177.3(5) . . . . ? C161 C41 C51 C61 -1.6(9) . . . . ? N11 C51 C61 C71 6.3(11) . . . . ? C41 C51 C61 C71 -170.2(6) . . . . ? C51 C61 C71 C81 178.9(6) . . . . ? C61 C71 C81 C91 169.2(6) . . . . ? C61 C71 C81 C131 -10.2(10) . . . . ? C131 C81 C91 C101 1.7(9) . . . . ? C71 C81 C91 C101 -177.7(5) . . . . ? C141 O21 C101 C111 -175.2(5) . . . . ? C141 O21 C101 C91 4.3(8) . . . . ? C81 C91 C101 O21 -179.6(5) . . . . ? C81 C91 C101 C111 -0.1(8) . . . . ? O21 C101 C111 O11 -0.7(7) . . . . ? C91 C101 C111 O11 179.8(4) . . . . ? O21 C101 C111 C121 177.8(4) . . . . ? C91 C101 C111 C121 -1.7(8) . . . . ? C101 C111 C121 C131 1.8(7) . . . . ? O11 C111 C121 C131 -179.6(4) . . . . ? C91 C81 C131 C121 -1.5(9) . . . . ? C71 C81 C131 C121 177.9(5) . . . . ? C111 C121 C131 C81 -0.3(8) . . . . ? C52 N12 N22 C32 0.2(5) . . . . ? N12 N22 C32 C42 -0.2(5) . . . . ? N12 N22 C32 C62 -179.7(4) . . . . ? N22 C32 C42 C52 0.1(5) . . . . ? C62 C32 C42 C52 179.5(5) . . . . ? N22 C32 C42 C162 176.8(5) . . . . ? C62 C32 C42 C162 -3.7(9) . . . . ? N22 N12 C52 C42 -0.2(5) . . . . ? N22 N12 C52 C152 -180.0(4) . . . . ? C32 C42 C52 N12 0.1(5) . . . . ? C162 C42 C52 N12 -176.9(4) . . . . ? C32 C42 C52 C152 179.8(5) . . . . ? C162 C42 C52 C152 2.8(8) . . . . ? N22 C32 C62 C72 -174.1(5) . . . . ? C42 C32 C62 C72 6.5(8) . . . . ? C32 C62 C72 C82 179.5(4) . . . . ? C62 C72 C82 C92 5.0(8) . . . . ? C62 C72 C82 C132 -174.8(5) . . . . ? C132 C82 C92 C102 -1.8(7) . . . . ? C72 C82 C92 C102 178.4(4) . . . . ? C142 O22 C102 C112 175.3(4) . . . . ? C142 O22 C102 C92 -4.9(7) . . . . ? C82 C92 C102 C112 0.6(7) . . . . ? C82 C92 C102 O22 -179.2(4) . . . . ? O22 C102 C112 O12 0.1(6) . . . . ? C92 C102 C112 O12 -179.7(4) . . . . ? O22 C102 C112 C122 -178.7(4) . . . . ? C92 C102 C112 C122 1.5(7) . . . . ? O12 C112 C122 C132 178.9(4) . . . . ? C102 C112 C122 C132 -2.3(7) . . . . ? C112 C122 C132 C82 1.1(7) . . . . ? C92 C82 C132 C122 1.0(7) . . . . ? C72 C82 C132 C122 -179.2(4) . . . . ? C53 N13 N23 C33 -0.6(5) . . . . ? N13 N23 C33 C43 0.6(5) . . . . ? N13 N23 C33 C63 -179.8(4) . . . . ? N23 C33 C43 C53 -0.4(5) . . . . ? C63 C33 C43 C53 -179.9(5) . . . . ? N23 C33 C43 C163 176.8(5) . . . . ? C63 C33 C43 C163 -2.7(9) . . . . ? C33 C43 C53 N13 0.1(5) . . . . ? C163 C43 C53 N13 -177.4(4) . . . . ? C33 C43 C53 C153 -177.9(5) . . . . ? C163 C43 C53 C153 4.6(9) . . . . ? N23 N13 C53 C43 0.4(6) . . . . ? N23 N13 C53 C153 178.6(4) . . . . ? N23 C33 C63 C73 -175.0(5) . . . . ? C43 C33 C63 C73 4.5(9) . . . . ? C33 C63 C73 C83 178.8(5) . . . . ? C63 C73 C83 C93 -14.5(8) . . . . ? C63 C73 C83 C133 167.6(5) . . . . ? C133 C83 C93 C103 -2.2(7) . . . . ? C73 C83 C93 C103 179.8(5) . . . . ? C143 O23 C103 C113 177.7(4) . . . . ? C143 O23 C103 C93 -1.2(7) . . . . ? C83 C93 C103 O23 179.8(5) . . . . ? C83 C93 C103 C113 0.9(7) . . . . ? O23 C103 C113 O13 1.3(7) . . . . ? C93 C103 C113 O13 -179.7(4) . . . . ? O23 C103 C113 C123 -178.4(5) . . . . ? C93 C103 C113 C123 0.6(7) . . . . ? O13 C113 C123 C133 179.7(5) . . . . ? C103 C113 C123 C133 -0.6(8) . . . . ? C93 C83 C133 C123 2.2(8) . . . . ? C73 C83 C133 C123 -179.9(5) . . . . ? C113 C123 C133 C83 -0.8(8) . . . . ? 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 O11 H111 O13 0.92 2.03 2.813(4) 141.3 2_946 O13 H113 N21 1.16 1.81 2.782(5) 137.3 . O12 H112 N22 1.14 1.57 2.673(4) 159.4 2_645 N11 H11 O11 1.08 2.01 2.951(5) 144.3 2_956 N12 H12 N23 1.10 1.82 2.914(5) 175.6 . N13 H13 O12 1.02 1.93 2.853(4) 148.6 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.950 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.155 # Attachment 'comp8.cif' data_comp8 _database_code_depnum_ccdc_archive 'CCDC 690492' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O2' _chemical_formula_weight 320.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.2363(13) _cell_length_b 8.2769(8) _cell_length_c 30.673(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3360.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.083 _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 296(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 'w 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 16484 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2954 _reflns_number_gt 1655 _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^)+(0.0909P)^2^+0.7726P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2954 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1168 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1848 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C3 C 0.8527(2) -0.1384(4) 0.43919(10) 0.0406(8) Uani 1 1 d . . . C4 C 0.7578(2) -0.0969(4) 0.45729(9) 0.0387(7) Uani 1 1 d . . . C5 C 0.7795(2) -0.0137(4) 0.49508(10) 0.0417(8) Uani 1 1 d . . . C6 C 0.7155(2) 0.0582(4) 0.52791(10) 0.0469(8) Uani 1 1 d . . . H6 H 0.6485 0.0784 0.5206 0.056 Uiso 1 1 calc R . . C7 C 0.7459(2) 0.0975(4) 0.56794(10) 0.0465(8) Uani 1 1 d . . . H7 H 0.8128 0.0732 0.5746 0.056 Uiso 1 1 calc R . . C8 C 0.6877(2) 0.1738(4) 0.60271(10) 0.0409(7) Uani 1 1 d . . . C9 C 0.7241(2) 0.1646(4) 0.64563(10) 0.0426(8) Uani 1 1 d . . . H9 H 0.7856 0.1138 0.6509 0.051 Uiso 1 1 calc R . . C10 C 0.6710(2) 0.2289(4) 0.67990(10) 0.0419(8) Uani 1 1 d . . . C11 C 0.5791(2) 0.3077(4) 0.67232(10) 0.0419(8) Uani 1 1 d . . . C12 C 0.5435(2) 0.3198(4) 0.63029(10) 0.0464(8) Uani 1 1 d . . . H12 H 0.4829 0.3730 0.6250 0.056 Uiso 1 1 calc R . . C13 C 0.5970(2) 0.2536(4) 0.59573(10) 0.0466(8) Uani 1 1 d . . . H13 H 0.5718 0.2629 0.5676 0.056 Uiso 1 1 calc R . . C14 C 0.7959(3) 0.1508(5) 0.73216(12) 0.0695(11) Uani 1 1 d . . . H14A H 0.7949 0.0397 0.7231 0.104 Uiso 1 1 calc R . . H14B H 0.8083 0.1564 0.7630 0.104 Uiso 1 1 calc R . . H14C H 0.8486 0.2069 0.7169 0.104 Uiso 1 1 calc R . . C15 C 0.4451(3) 0.4655(5) 0.70199(12) 0.0751(12) Uani 1 1 d . . . H15A H 0.4623 0.5531 0.6828 0.113 Uiso 1 1 calc R . . H15B H 0.4228 0.5081 0.7295 0.113 Uiso 1 1 calc R . . H15C H 0.3920 0.4025 0.6892 0.113 Uiso 1 1 calc R . . C16 C 0.6534(2) -0.1419(4) 0.44207(11) 0.0529(9) Uani 1 1 d . . . H16A H 0.6050 -0.1127 0.4640 0.079 Uiso 1 1 calc R . . H16B H 0.6503 -0.2563 0.4370 0.079 Uiso 1 1 calc R . . H16C H 0.6383 -0.0855 0.4155 0.079 Uiso 1 1 calc R . . C17 C 0.8801(2) -0.2312(4) 0.39973(10) 0.0397(7) Uani 1 1 d . . . C18 C 0.8114(2) -0.2619(4) 0.36636(11) 0.0537(9) Uani 1 1 d . . . H18 H 0.7457 -0.2230 0.3685 0.064 Uiso 1 1 calc R . . C19 C 0.8400(3) -0.3498(5) 0.33011(11) 0.0611(10) Uani 1 1 d . . . H19 H 0.7931 -0.3701 0.3082 0.073 Uiso 1 1 calc R . . C20 C 0.9365(3) -0.4075(4) 0.32586(11) 0.0579(9) Uani 1 1 d . . . H20 H 0.9551 -0.4662 0.3013 0.070 Uiso 1 1 calc R . . C21 C 1.0055(3) -0.3776(4) 0.35827(11) 0.0558(9) Uani 1 1 d . . . H21 H 1.0713 -0.4158 0.3556 0.067 Uiso 1 1 calc R . . C22 C 0.9775(2) -0.2914(4) 0.39472(11) 0.0488(8) Uani 1 1 d . . . H22 H 1.0250 -0.2729 0.4165 0.059 Uiso 1 1 calc R . . N1 N 0.88193(19) -0.0076(3) 0.49796(8) 0.0472(7) Uani 1 1 d . . . H1 H 0.924(3) 0.037(5) 0.5179(13) 0.100 Uiso 1 1 d . . . N2 N 0.92781(18) -0.0832(3) 0.46430(8) 0.0474(7) Uani 1 1 d . . . O1 O 0.53121(16) 0.3666(3) 0.70860(7) 0.0571(7) Uani 1 1 d . . . O2 O 0.70162(17) 0.2233(3) 0.72262(7) 0.0571(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0361(17) 0.0473(18) 0.0385(18) 0.0007(15) -0.0052(14) -0.0015(14) C4 0.0339(16) 0.0448(18) 0.0374(17) 0.0027(14) -0.0037(13) -0.0029(14) C5 0.0357(17) 0.052(2) 0.0370(18) 0.0035(15) -0.0011(13) -0.0019(14) C6 0.0348(16) 0.060(2) 0.045(2) -0.0030(17) -0.0003(14) -0.0007(15) C7 0.0398(17) 0.056(2) 0.0439(19) -0.0007(16) 0.0024(15) 0.0036(15) C8 0.0382(17) 0.0458(18) 0.0387(18) 0.0008(15) 0.0013(14) -0.0053(14) C9 0.0388(17) 0.0453(18) 0.0436(19) -0.0010(15) -0.0014(14) 0.0057(14) C10 0.0426(17) 0.0458(18) 0.0374(18) -0.0025(15) -0.0040(14) 0.0006(15) C11 0.0368(17) 0.0438(18) 0.045(2) -0.0027(15) 0.0036(14) 0.0016(14) C12 0.0351(17) 0.055(2) 0.049(2) -0.0008(17) -0.0051(15) 0.0021(15) C13 0.0416(17) 0.056(2) 0.0417(19) 0.0042(15) -0.0053(15) -0.0017(16) C14 0.068(2) 0.083(3) 0.058(2) -0.006(2) -0.0160(19) 0.028(2) C15 0.056(2) 0.095(3) 0.075(3) -0.007(2) 0.009(2) 0.023(2) C16 0.0399(18) 0.065(2) 0.054(2) -0.0080(18) -0.0061(15) -0.0019(16) C17 0.0395(17) 0.0424(17) 0.0372(18) 0.0019(14) -0.0019(14) -0.0025(14) C18 0.0461(19) 0.069(2) 0.046(2) -0.0095(18) -0.0078(15) 0.0055(17) C19 0.060(2) 0.078(3) 0.045(2) -0.0155(19) -0.0093(17) -0.005(2) C20 0.066(2) 0.063(2) 0.044(2) -0.0094(18) 0.0075(18) 0.0070(19) C21 0.052(2) 0.059(2) 0.057(2) -0.0036(18) 0.0031(18) 0.0101(17) C22 0.0450(18) 0.054(2) 0.047(2) -0.0023(17) -0.0078(15) 0.0021(16) N1 0.0349(14) 0.0684(19) 0.0383(17) -0.0083(14) -0.0017(11) -0.0040(13) N2 0.0355(14) 0.0667(18) 0.0401(15) -0.0078(14) -0.0011(12) -0.0032(13) O1 0.0493(14) 0.0703(16) 0.0517(15) -0.0057(12) 0.0021(11) 0.0172(12) O2 0.0604(15) 0.0704(16) 0.0405(14) -0.0067(12) -0.0070(11) 0.0181(12) _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 C3 N2 1.339(4) . ? C3 C4 1.415(4) . ? C3 C17 1.479(4) . ? C4 C5 1.379(4) . ? C4 C16 1.505(4) . ? C5 N1 1.360(4) . ? C5 C6 1.444(4) . ? C6 C7 1.333(4) . ? C6 H6 0.9300 . ? C7 C8 1.460(4) . ? C7 H7 0.9300 . ? C8 C13 1.386(4) . ? C8 C9 1.404(4) . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 O2 1.372(3) . ? C10 C11 1.399(4) . ? C11 C12 1.376(4) . ? C11 O1 1.371(3) . ? C12 C13 1.387(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O2 1.416(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O1 1.418(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.391(4) . ? C17 C18 1.393(4) . ? C18 C19 1.382(4) . ? C18 H18 0.9300 . ? C19 C20 1.370(5) . ? C19 H19 0.9300 . ? C20 C21 1.372(5) . ? C20 H20 0.9300 . ? C21 C22 1.377(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N1 N2 1.351(3) . ? N1 H1 0.90(4) . ? 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 N2 C3 C4 110.5(3) . . ? N2 C3 C17 117.8(3) . . ? C4 C3 C17 131.7(3) . . ? C5 C4 C3 105.4(2) . . ? C5 C4 C16 125.1(3) . . ? C3 C4 C16 129.2(3) . . ? C4 C5 N1 106.3(3) . . ? C4 C5 C6 132.1(3) . . ? N1 C5 C6 121.6(3) . . ? C7 C6 C5 124.5(3) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C6 C7 C8 128.3(3) . . ? C6 C7 H7 115.9 . . ? C8 C7 H7 115.9 . . ? C13 C8 C9 117.9(3) . . ? C13 C8 C7 123.4(3) . . ? C9 C8 C7 118.7(3) . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? O2 C10 C9 124.5(3) . . ? O2 C10 C11 115.6(3) . . ? C9 C10 C11 119.9(3) . . ? C12 C11 O1 125.2(3) . . ? C12 C11 C10 119.2(3) . . ? O1 C11 C10 115.6(3) . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C8 C13 C12 120.8(3) . . ? C8 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C16 H16A 109.5 . . ? C4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 117.3(3) . . ? C22 C17 C3 120.3(3) . . ? C18 C17 C3 122.4(3) . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 121.1(3) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 119.2(3) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 121.6(3) . . ? C17 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? N2 N1 C5 112.4(2) . . ? N2 N1 H1 115(3) . . ? C5 N1 H1 132(3) . . ? C3 N2 N1 105.3(2) . . ? C11 O1 C15 117.5(3) . . ? C10 O2 C14 118.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C3 C4 C5 -0.3(4) . . . . ? C17 C3 C4 C5 178.1(3) . . . . ? N2 C3 C4 C16 -175.7(3) . . . . ? C17 C3 C4 C16 2.7(6) . . . . ? C3 C4 C5 N1 0.4(3) . . . . ? C16 C4 C5 N1 176.1(3) . . . . ? C3 C4 C5 C6 -179.3(3) . . . . ? C16 C4 C5 C6 -3.7(5) . . . . ? C4 C5 C6 C7 161.5(3) . . . . ? N1 C5 C6 C7 -18.2(5) . . . . ? C5 C6 C7 C8 178.3(3) . . . . ? C6 C7 C8 C13 -16.5(5) . . . . ? C6 C7 C8 C9 162.6(3) . . . . ? C13 C8 C9 C10 1.5(5) . . . . ? C7 C8 C9 C10 -177.6(3) . . . . ? C8 C9 C10 O2 179.5(3) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? O2 C10 C11 C12 179.4(3) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? O2 C10 C11 O1 -0.9(4) . . . . ? C9 C10 C11 O1 179.4(3) . . . . ? O1 C11 C12 C13 -178.9(3) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C9 C8 C13 C12 -1.0(5) . . . . ? C7 C8 C13 C12 178.1(3) . . . . ? C11 C12 C13 C8 -0.1(5) . . . . ? N2 C3 C17 C22 15.1(4) . . . . ? C4 C3 C17 C22 -163.2(3) . . . . ? N2 C3 C17 C18 -164.8(3) . . . . ? C4 C3 C17 C18 16.8(5) . . . . ? C22 C17 C18 C19 0.4(5) . . . . ? C3 C17 C18 C19 -179.7(3) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? C18 C19 C20 C21 0.2(6) . . . . ? C19 C20 C21 C22 0.4(5) . . . . ? C18 C17 C22 C21 0.2(5) . . . . ? C3 C17 C22 C21 -179.8(3) . . . . ? C20 C21 C22 C17 -0.6(5) . . . . ? C4 C5 N1 N2 -0.4(4) . . . . ? C6 C5 N1 N2 179.4(3) . . . . ? C4 C3 N2 N1 0.1(3) . . . . ? C17 C3 N2 N1 -178.6(3) . . . . ? C5 N1 N2 C3 0.2(3) . . . . ? C12 C11 O1 C15 -8.6(5) . . . . ? C10 C11 O1 C15 171.8(3) . . . . ? C9 C10 O2 C14 2.0(5) . . . . ? C11 C10 O2 C14 -177.6(3) . . . . ? 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 N1 H1 N2 0.90(4) 2.07(4) 2.872(3) 147(4) 5_756 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.193 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.049