data_mj47s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 N O3' _chemical_formula_weight 375.45 _chemical_absolute_configuration rmad 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.414(2) _cell_length_b 8.499(2) _cell_length_c 11.529(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.28(3) _cell_angle_gamma 90.00 _cell_volume 1011.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9338 _cell_measurement_theta_min 1.9192 _cell_measurement_theta_max 31.1992 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9695 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details 'Oxford Diffraction CrysAlis' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Oxford Sapphire CCD' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean 8.2564 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9338 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 31.27 _reflns_number_total 5020 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis' _computing_cell_refinement 'Oxford Diffraction CrysAlis' _computing_data_reduction 'Oxford Diffraction CrysAlis' _computing_structure_solution 'SHELX-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(14) _refine_ls_number_reflns 5020 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 C1 C 0.7983(2) 0.2775(3) 0.5994(2) 0.0328(5) Uani 1 1 d . . . C2 C 0.8267(2) 0.0997(3) 0.5926(2) 0.0349(6) Uani 1 1 d . . . H2A H 0.7643 0.0418 0.6140 0.042 Uiso 1 1 calc R . . O1 O 0.87875(16) 0.3689(2) 0.56051(16) 0.0450(5) Uani 1 1 d . . . H1O H 0.9465 0.3894 0.6231 0.054 Uiso 1 1 calc R . . C3 C 0.9620(3) 0.0410(3) 0.6851(3) 0.0460(7) Uani 1 1 d . . . H3A H 0.9822 0.0868 0.7695 0.055 Uiso 1 1 calc R . . C4 C 1.0714(3) 0.0846(4) 0.6494(3) 0.0607(9) Uani 1 1 d . . . H4A H 1.1527 0.0534 0.7171 0.073 Uiso 1 1 calc R . . H4B H 1.0713 0.1963 0.6370 0.073 Uiso 1 1 calc R . . H4C H 1.0594 0.0317 0.5715 0.073 Uiso 1 1 calc R . . C5 C 0.9579(3) -0.1367(4) 0.6982(3) 0.0733(10) Uani 1 1 d . . . H5A H 0.9246 -0.1842 0.6147 0.088 Uiso 1 1 calc R . . H5B H 0.9027 -0.1628 0.7391 0.088 Uiso 1 1 calc R . . H5C H 1.0438 -0.1753 0.7491 0.088 Uiso 1 1 calc R . . C6 C 0.6970(2) -0.0156(3) 0.3823(2) 0.0439(6) Uani 1 1 d . . . H6A H 0.6318 -0.0305 0.4094 0.053 Uiso 1 1 calc R . . N1 N 0.80077(19) 0.0553(2) 0.46012(18) 0.0367(5) Uani 1 1 d . . . H1N H 0.8583 0.0781 0.4332 0.044 Uiso 0.92 1 calc PR . . C7 C 0.6740(2) -0.0725(3) 0.2594(2) 0.0433(6) Uani 1 1 d . . . C8 C 0.7726(2) -0.0624(3) 0.2154(2) 0.0378(6) Uani 1 1 d . . . O2 O 0.88305(17) 0.0031(2) 0.27909(17) 0.0452(5) Uani 1 1 d . . . H2O H 0.9349 -0.0284 0.2523 0.054 Uiso 0.08 1 calc PR . . C9 C 0.7453(3) -0.1364(4) 0.0959(2) 0.0457(6) Uani 1 1 d . . . O3 O 0.83930(19) -0.1303(3) 0.05212(18) 0.0653(6) Uani 1 1 d . . . H3O H 0.8967 -0.0697 0.0970 0.078 Uiso 1 1 calc R . . C10 C 0.6330(3) -0.2138(4) 0.0286(3) 0.0603(9) Uani 1 1 d . . . H10A H 0.6201 -0.2646 -0.0473 0.072 Uiso 1 1 calc R . . C11 C 0.5365(3) -0.2180(5) 0.0723(3) 0.0754(11) Uani 1 1 d . . . H11A H 0.4581 -0.2678 0.0238 0.091 Uiso 1 1 calc R . . C12 C 0.5564(3) -0.1498(5) 0.1848(3) 0.0697(10) Uani 1 1 d . . . H12A H 0.4918 -0.1539 0.2136 0.084 Uiso 1 1 calc R . . C13 C 0.6586(2) 0.3081(3) 0.5001(2) 0.0351(5) Uani 1 1 d . . . C14 C 0.6324(3) 0.3956(3) 0.3919(2) 0.0467(7) Uani 1 1 d . . . H14A H 0.6997 0.4457 0.3816 0.056 Uiso 1 1 calc R . . C15 C 0.5066(3) 0.4101(4) 0.2978(3) 0.0555(8) Uani 1 1 d . . . H15A H 0.4904 0.4712 0.2256 0.067 Uiso 1 1 calc R . . C16 C 0.4068(3) 0.3359(4) 0.3098(3) 0.0555(8) Uani 1 1 d . . . H16A H 0.3233 0.3425 0.2445 0.067 Uiso 1 1 calc R . . C17 C 0.4301(3) 0.2508(4) 0.4195(3) 0.0542(8) Uani 1 1 d . . . H17A H 0.3621 0.2020 0.4296 0.065 Uiso 1 1 calc R . . C18 C 0.5552(3) 0.2387(3) 0.5143(3) 0.0449(7) Uani 1 1 d . . . H18A H 0.5705 0.1830 0.5888 0.054 Uiso 1 1 calc R . . C19 C 0.8128(2) 0.3249(3) 0.7327(2) 0.0337(6) Uani 1 1 d . . . C20 C 0.8410(3) 0.4813(3) 0.7695(3) 0.0468(7) Uani 1 1 d . . . H20A H 0.8551 0.5514 0.7149 0.056 Uiso 1 1 calc R . . C21 C 0.8483(3) 0.5348(4) 0.8860(3) 0.0593(8) Uani 1 1 d . . . H21A H 0.8677 0.6397 0.9091 0.071 Uiso 1 1 calc R . . C22 C 0.8270(3) 0.4331(4) 0.9668(3) 0.0622(9) Uani 1 1 d . . . H22A H 0.8307 0.4692 1.0444 0.075 Uiso 1 1 calc R . . C23 C 0.8000(3) 0.2775(4) 0.9333(3) 0.0576(8) Uani 1 1 d . . . H23A H 0.7863 0.2081 0.9887 0.069 Uiso 1 1 calc R . . C24 C 0.7935(3) 0.2243(3) 0.8177(3) 0.0451(7) Uani 1 1 d . . . H24A H 0.7757 0.1187 0.7963 0.054 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 C1 0.0345(12) 0.0336(13) 0.0325(12) 0.0001(10) 0.0163(10) -0.0024(10) C2 0.0380(13) 0.0384(14) 0.0290(12) -0.0034(10) 0.0149(11) -0.0004(11) O1 0.0420(10) 0.0523(11) 0.0400(9) 0.0047(9) 0.0169(8) -0.0117(9) C3 0.0436(15) 0.0497(17) 0.0386(14) -0.0078(13) 0.0118(12) 0.0092(13) C4 0.0389(15) 0.064(2) 0.070(2) -0.0187(17) 0.0146(15) 0.0032(14) C5 0.073(2) 0.054(2) 0.076(2) 0.0121(19) 0.0152(17) 0.0212(18) C6 0.0403(14) 0.0529(16) 0.0401(14) -0.0089(12) 0.0187(12) -0.0084(13) N1 0.0366(12) 0.0427(12) 0.0314(11) -0.0078(9) 0.0151(9) -0.0034(10) C7 0.0385(14) 0.0543(17) 0.0336(13) -0.0091(12) 0.0119(11) -0.0062(13) C8 0.0364(13) 0.0382(14) 0.0340(12) -0.0021(11) 0.0106(11) -0.0008(12) O2 0.0389(10) 0.0499(12) 0.0470(10) -0.0085(9) 0.0186(8) -0.0041(8) C9 0.0510(16) 0.0519(17) 0.0333(13) -0.0012(13) 0.0171(12) 0.0011(14) O3 0.0659(14) 0.0851(16) 0.0554(12) -0.0229(12) 0.0358(11) -0.0097(13) C10 0.064(2) 0.077(2) 0.0312(14) -0.0158(14) 0.0120(14) -0.0149(17) C11 0.060(2) 0.115(3) 0.0445(17) -0.0292(19) 0.0161(15) -0.036(2) C12 0.0494(18) 0.109(3) 0.0498(17) -0.0217(19) 0.0205(14) -0.029(2) C13 0.0359(13) 0.0322(13) 0.0360(13) -0.0036(11) 0.0141(10) 0.0008(10) C14 0.0485(16) 0.0503(17) 0.0420(14) 0.0033(13) 0.0200(13) -0.0017(13) C15 0.0543(18) 0.058(2) 0.0442(16) 0.0045(14) 0.0119(14) 0.0065(16) C16 0.0431(16) 0.059(2) 0.0518(17) -0.0090(15) 0.0085(13) 0.0097(15) C17 0.0406(16) 0.059(2) 0.0610(19) -0.0027(16) 0.0200(14) -0.0010(14) C18 0.0424(15) 0.0472(16) 0.0462(15) 0.0044(13) 0.0200(13) 0.0004(12) C19 0.0324(13) 0.0368(14) 0.0304(12) -0.0046(10) 0.0119(10) 0.0025(10) C20 0.0527(16) 0.0398(15) 0.0437(15) -0.0035(12) 0.0165(13) 0.0038(13) C21 0.066(2) 0.0481(18) 0.0510(18) -0.0171(15) 0.0133(16) 0.0095(15) C22 0.068(2) 0.075(2) 0.0350(15) -0.0126(16) 0.0142(14) 0.0210(18) C23 0.0611(19) 0.076(2) 0.0397(15) 0.0017(15) 0.0253(14) 0.0066(17) C24 0.0522(16) 0.0458(16) 0.0403(14) -0.0028(12) 0.0226(12) -0.0019(13) _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 C1 O1 1.414(3) . ? C1 C19 1.528(3) . ? C1 C13 1.537(3) . ? C1 C2 1.554(3) . ? C2 N1 1.476(3) . ? C2 C3 1.537(3) . ? C2 H2A 0.9800 . ? O1 H1O 0.8200 . ? C3 C4 1.518(4) . ? C3 C5 1.520(4) . ? C3 H3A 0.9800 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N1 1.290(3) . ? C6 C7 1.412(3) . ? C6 H6A 0.9300 . ? N1 H1N 0.8600 . ? C7 C12 1.409(4) . ? C7 C8 1.421(3) . ? C8 O2 1.284(3) . ? C8 C9 1.423(3) . ? O2 H2O 0.8200 . ? C9 C10 1.352(4) . ? C9 O3 1.369(3) . ? O3 H3O 0.8200 . ? C10 C11 1.394(4) . ? C10 H10A 0.9300 . ? C11 C12 1.348(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.371(4) . ? C13 C18 1.389(4) . ? C14 C15 1.387(4) . ? C14 H14A 0.9300 . ? C15 C16 1.361(4) . ? C15 H15A 0.9300 . ? C16 C17 1.381(4) . ? C16 H16A 0.9300 . ? C17 C18 1.382(4) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C24 1.388(3) . ? C19 C20 1.391(4) . ? C20 C21 1.385(4) . ? C20 H20A 0.9300 . ? C21 C22 1.367(4) . ? C21 H21A 0.9300 . ? C22 C23 1.376(5) . ? C22 H22A 0.9300 . ? C23 C24 1.378(4) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? 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 O1 C1 C19 111.59(19) . . ? O1 C1 C13 106.17(18) . . ? C19 C1 C13 109.67(18) . . ? O1 C1 C2 109.91(19) . . ? C19 C1 C2 111.84(18) . . ? C13 C1 C2 107.43(18) . . ? N1 C2 C3 109.4(2) . . ? N1 C2 C1 110.28(19) . . ? C3 C2 C1 116.7(2) . . ? N1 C2 H2A 106.6 . . ? C3 C2 H2A 106.6 . . ? C1 C2 H2A 106.6 . . ? C1 O1 H1O 109.5 . . ? C4 C3 C5 109.5(3) . . ? C4 C3 C2 115.6(2) . . ? C5 C3 C2 109.1(2) . . ? C4 C3 H3A 107.5 . . ? C5 C3 H3A 107.5 . . ? C2 C3 H3A 107.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 125.5(2) . . ? N1 C6 H6A 117.3 . . ? C7 C6 H6A 117.3 . . ? C6 N1 C2 124.0(2) . . ? C6 N1 H1N 118.0 . . ? C2 N1 H1N 118.0 . . ? C12 C7 C6 119.5(2) . . ? C12 C7 C8 120.2(2) . . ? C6 C7 C8 120.1(2) . . ? O2 C8 C7 123.8(2) . . ? O2 C8 C9 120.1(2) . . ? C7 C8 C9 116.0(2) . . ? C8 O2 H2O 109.5 . . ? C10 C9 O3 120.5(2) . . ? C10 C9 C8 122.2(2) . . ? O3 C9 C8 117.3(2) . . ? C9 O3 H3O 109.5 . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C7 120.9(3) . . ? C11 C12 H12A 119.6 . . ? C7 C12 H12A 119.6 . . ? C14 C13 C18 118.1(2) . . ? C14 C13 C1 121.5(2) . . ? C18 C13 C1 120.2(2) . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C16 C17 C18 119.6(3) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C17 C18 C13 121.2(3) . . ? C17 C18 H18A 119.4 . . ? C13 C18 H18A 119.4 . . ? C24 C19 C20 117.3(2) . . ? C24 C19 C1 124.5(2) . . ? C20 C19 C1 118.1(2) . . ? C21 C20 C19 121.3(3) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C22 C23 C24 120.0(3) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C23 C24 C19 121.4(3) . . ? C23 C24 H24A 119.3 . . ? C19 C24 H24A 119.3 . . ? 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 O1 C1 C2 N1 -60.4(2) . . . . ? C19 C1 C2 N1 175.08(18) . . . . ? C13 C1 C2 N1 54.7(2) . . . . ? O1 C1 C2 C3 65.3(3) . . . . ? C19 C1 C2 C3 -59.2(3) . . . . ? C13 C1 C2 C3 -179.6(2) . . . . ? N1 C2 C3 C4 50.8(3) . . . . ? C1 C2 C3 C4 -75.3(3) . . . . ? N1 C2 C3 C5 -73.0(3) . . . . ? C1 C2 C3 C5 160.9(2) . . . . ? C7 C6 N1 C2 -173.9(2) . . . . ? C3 C2 N1 C6 129.5(3) . . . . ? C1 C2 N1 C6 -100.8(3) . . . . ? N1 C6 C7 C12 179.2(3) . . . . ? N1 C6 C7 C8 3.9(5) . . . . ? C12 C7 C8 O2 -178.5(3) . . . . ? C6 C7 C8 O2 -3.2(4) . . . . ? C12 C7 C8 C9 -1.2(4) . . . . ? C6 C7 C8 C9 174.1(2) . . . . ? O2 C8 C9 C10 176.5(3) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? O2 C8 C9 O3 -1.8(4) . . . . ? C7 C8 C9 O3 -179.2(3) . . . . ? O3 C9 C10 C11 -179.0(3) . . . . ? C8 C9 C10 C11 2.8(5) . . . . ? C9 C10 C11 C12 -2.6(6) . . . . ? C10 C11 C12 C7 0.5(6) . . . . ? C6 C7 C12 C11 -173.9(3) . . . . ? C8 C7 C12 C11 1.4(5) . . . . ? O1 C1 C13 C14 6.4(3) . . . . ? C19 C1 C13 C14 127.1(2) . . . . ? C2 C1 C13 C14 -111.2(3) . . . . ? O1 C1 C13 C18 -177.7(2) . . . . ? C19 C1 C13 C18 -57.0(3) . . . . ? C2 C1 C13 C18 64.7(3) . . . . ? C18 C13 C14 C15 -1.9(4) . . . . ? C1 C13 C14 C15 174.1(2) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C14 C15 C16 C17 2.8(5) . . . . ? C15 C16 C17 C18 -1.7(4) . . . . ? C16 C17 C18 C13 -1.2(4) . . . . ? C14 C13 C18 C17 3.0(4) . . . . ? C1 C13 C18 C17 -173.0(2) . . . . ? O1 C1 C19 C24 -151.7(2) . . . . ? C13 C1 C19 C24 90.9(3) . . . . ? C2 C1 C19 C24 -28.2(3) . . . . ? O1 C1 C19 C20 31.6(3) . . . . ? C13 C1 C19 C20 -85.7(3) . . . . ? C2 C1 C19 C20 155.2(2) . . . . ? C24 C19 C20 C21 -0.5(4) . . . . ? C1 C19 C20 C21 176.3(2) . . . . ? C19 C20 C21 C22 -0.4(4) . . . . ? C20 C21 C22 C23 0.9(5) . . . . ? C21 C22 C23 C24 -0.6(5) . . . . ? C22 C23 C24 C19 -0.4(4) . . . . ? C20 C19 C24 C23 0.9(4) . . . . ? C1 C19 C24 C23 -175.8(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 N1 H1N O1 0.86 2.83 2.890(3) 85.2 . _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.156 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.036