data_ya11sad _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 N2 O2' _chemical_formula_sum 'C19 H24 N2 O2' _chemical_formula_weight 312.40 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_int_tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.6027(14) _cell_length_b 10.0645(16) _cell_length_c 11.0930(17) _cell_angle_alpha 110.209(3) _cell_angle_beta 109.260(3) _cell_angle_gamma 101.701(3) _cell_volume 887.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 953 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 24.06 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9985 _exptl_absorpt_correction_T_max 0.9992 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'normal-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 5068 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3898 _reflns_number_gt 3411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0625P)^2^+0.0963P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(15) _refine_ls_number_reflns 3898 _refine_ls_number_parameters 421 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 O1 O 0.6262(3) 0.2429(3) 0.7109(3) 0.0476(6) Uani 1 1 d . . . O2 O 0.5551(3) 0.6436(3) 0.9486(3) 0.0529(7) Uani 1 1 d . . . H2 H 0.5758 0.6294 1.0219 0.079 Uiso 1 1 calc R . . O3 O 1.1061(3) 0.1970(3) 0.6802(3) 0.0462(6) Uani 1 1 d . . . O4 O 0.7110(3) -0.2165(3) 0.4394(3) 0.0642(8) Uani 1 1 d . . . H4 H 0.6775 -0.2040 0.3655 0.096 Uiso 1 1 calc R . . N1 N 0.3633(3) 0.1332(3) 0.6242(3) 0.0432(7) Uani 1 1 d . . . H1 H 0.2765 0.1462 0.6275 0.052 Uiso 1 1 calc R . . N2 N 0.5970(4) 0.4857(4) 1.1025(3) 0.0550(9) Uani 1 1 d . . . H2B H 0.5645 0.4637 1.1611 0.066 Uiso 1 1 calc R . . H2C H 0.6314 0.5805 1.1174 0.066 Uiso 1 1 calc R . . N3 N 0.9438(3) 0.3127(3) 0.7355(3) 0.0346(6) Uani 1 1 d . . . H3 H 0.8455 0.3039 0.7195 0.041 Uiso 1 1 calc R . . N4 N 0.6794(5) -0.0680(4) 0.2762(4) 0.0670(10) Uani 1 1 d . . . H4A H 0.6094 -0.0505 0.2149 0.080 Uiso 1 1 calc R . . H4B H 0.6652 -0.1612 0.2658 0.080 Uiso 1 1 calc R . . C1 C 0.5012(4) 0.2440(4) 0.7193(3) 0.0348(8) Uani 1 1 d . . . C2 C 0.4982(4) 0.3701(4) 0.8398(3) 0.0314(7) Uani 1 1 d . . . H2A H 0.3864 0.3514 0.8258 0.038 Uiso 1 1 calc R . . C3 C 0.5651(4) 0.5240(4) 0.8409(4) 0.0405(8) Uani 1 1 d . . . H3A H 0.6784 0.5451 0.8594 0.049 Uiso 1 1 calc R . . C4 C 0.4751(6) 0.5244(5) 0.7006(5) 0.0636(12) Uani 1 1 d . . . H4C H 0.3631 0.4999 0.6799 0.095 Uiso 1 1 calc R . . H4D H 0.4863 0.4485 0.6242 0.095 Uiso 1 1 calc R . . H4E H 0.5175 0.6249 0.7068 0.095 Uiso 1 1 calc R . . C5 C 0.5938(4) 0.3637(4) 0.9793(4) 0.0381(8) Uani 1 1 d . . . H5 H 0.7050 0.3830 0.9914 0.046 Uiso 1 1 calc R . . C6 C 0.3482(5) -0.0084(5) 0.5149(4) 0.0540(10) Uani 1 1 d . . . H6 H 0.4483 0.0086 0.5031 0.065 Uiso 1 1 calc R . . C7 C 0.3333(9) -0.1292(6) 0.5681(6) 0.103(2) Uani 1 1 d . . . H7A H 0.4299 -0.0991 0.6537 0.154 Uiso 1 1 calc R . . H7B H 0.3177 -0.2263 0.4936 0.154 Uiso 1 1 calc R . . H7C H 0.2428 -0.1398 0.5911 0.154 Uiso 1 1 calc R . . C8 C 0.5312(4) 0.2083(4) 0.9704(4) 0.0403(8) Uani 1 1 d . . . C9 C 0.3812(5) 0.1511(5) 0.9589(5) 0.0574(11) Uani 1 1 d . . . H9 H 0.3174 0.2119 0.9606 0.069 Uiso 1 1 calc R . . C10 C 0.3232(5) 0.0069(6) 0.9452(6) 0.0714(14) Uani 1 1 d . . . H10 H 0.2199 -0.0304 0.9373 0.086 Uiso 1 1 calc R . . C11 C 0.4132(5) -0.0835(5) 0.9427(5) 0.0605(11) Uani 1 1 d . . . H11 H 0.3722 -0.1833 0.9319 0.073 Uiso 1 1 calc R . . C12 C 0.5624(5) -0.0277(4) 0.9560(4) 0.0513(10) Uani 1 1 d . . . H12 H 0.6265 -0.0883 0.9562 0.062 Uiso 1 1 calc R . . C13 C 0.6201(4) 0.1154(4) 0.9689(4) 0.0446(9) Uani 1 1 d . . . H13 H 0.7237 0.1519 0.9771 0.054 Uiso 1 1 calc R . . C14 C 0.2155(4) -0.0482(4) 0.3747(4) 0.0452(9) Uani 1 1 d . . . C15 C 0.0840(5) -0.1801(5) 0.3036(5) 0.0606(11) Uani 1 1 d . . . H15 H 0.0779 -0.2490 0.3441 0.073 Uiso 1 1 calc R . . C16 C -0.0354(6) -0.2139(8) 0.1788(6) 0.0903(17) Uani 1 1 d . . . H16 H -0.1244 -0.3047 0.1346 0.108 Uiso 1 1 calc R . . C17 C -0.0312(8) -0.1253(9) 0.1180(6) 0.099(2) Uani 1 1 d . . . H17 H -0.1175 -0.1522 0.0303 0.118 Uiso 1 1 calc R . . C18 C 0.0960(12) 0.0079(9) 0.1775(8) 0.107(2) Uani 1 1 d . . . H18 H 0.0993 0.0714 0.1312 0.129 Uiso 1 1 calc R . . C19 C 0.2216(7) 0.0461(6) 0.3104(6) 0.0726(14) Uani 1 1 d . . . H19 H 0.3100 0.1373 0.3549 0.087 Uiso 1 1 calc R . . C20 C 0.9710(4) 0.1952(4) 0.6585(3) 0.0328(7) Uani 1 1 d . . . C21 C 0.8286(4) 0.0590(4) 0.5391(3) 0.0356(7) Uani 1 1 d . . . H21 H 0.7313 0.0714 0.5484 0.043 Uiso 1 1 calc R . . C22 C 0.8430(4) -0.0842(4) 0.5507(4) 0.0440(8) Uani 1 1 d . . . H22 H 0.9417 -0.0951 0.5440 0.053 Uiso 1 1 calc R . . C23 C 0.8495(6) -0.0806(5) 0.6897(5) 0.0620(11) Uani 1 1 d . . . H23A H 0.7570 -0.0621 0.7007 0.093 Uiso 1 1 calc R . . H23B H 0.9459 0.0008 0.7692 0.093 Uiso 1 1 calc R . . H23C H 0.8497 -0.1780 0.6895 0.093 Uiso 1 1 calc R . . C24 C 0.8197(4) 0.0581(4) 0.3958(4) 0.0424(8) Uani 1 1 d . . . H24 H 0.9143 0.0389 0.3857 0.051 Uiso 1 1 calc R . . C25 C 1.0697(4) 0.4552(4) 0.8452(4) 0.0368(8) Uani 1 1 d . . . H25 H 1.1609 0.4655 0.8200 0.044 Uiso 1 1 calc R . . C26 C 1.0140(5) 0.5862(4) 0.8434(5) 0.0525(10) Uani 1 1 d . . . H26A H 0.9830 0.5825 0.7485 0.079 Uiso 1 1 calc R . . H26B H 1.0999 0.6825 0.9145 0.079 Uiso 1 1 calc R . . H26C H 0.9232 0.5778 0.8661 0.079 Uiso 1 1 calc R . . C27 C 0.8298(5) 0.2128(4) 0.4013(4) 0.0433(8) Uani 1 1 d . . . C28 C 0.7012(6) 0.2592(6) 0.3883(5) 0.0637(12) Uani 1 1 d . . . H28 H 0.6027 0.1908 0.3672 0.076 Uiso 1 1 calc R . . C29 C 0.7171(7) 0.4072(6) 0.4062(5) 0.0753(15) Uani 1 1 d . . . H29 H 0.6293 0.4393 0.3975 0.090 Uiso 1 1 calc R . . C30 C 0.8584(8) 0.5050(6) 0.4363(5) 0.0770(16) Uani 1 1 d . . . H30 H 0.8687 0.6053 0.4487 0.092 Uiso 1 1 calc R . . C31 C 0.9846(7) 0.4603(5) 0.4485(5) 0.0716(14) Uani 1 1 d . . . H31 H 1.0830 0.5290 0.4696 0.086 Uiso 1 1 calc R . . C32 C 0.9687(5) 0.3138(5) 0.4300(4) 0.0558(11) Uani 1 1 d . . . H32 H 1.0571 0.2828 0.4376 0.067 Uiso 1 1 calc R . . C33 C 1.1271(4) 0.4603(4) 0.9924(4) 0.0388(8) Uani 1 1 d . . . C34 C 1.2705(4) 0.5638(5) 1.1003(4) 0.0522(10) Uani 1 1 d . . . H34 H 1.3332 0.6334 1.0819 0.063 Uiso 1 1 calc R . . C35 C 1.3263(5) 0.5702(6) 1.2335(4) 0.0640(12) Uani 1 1 d . . . H35 H 1.4263 0.6425 1.3061 0.077 Uiso 1 1 calc R . . C36 C 1.2352(6) 0.4701(6) 1.2610(5) 0.0658(12) Uani 1 1 d . . . H36 H 1.2732 0.4718 1.3524 0.079 Uiso 1 1 calc R . . C37 C 1.0898(6) 0.3684(5) 1.1563(5) 0.0654(12) Uani 1 1 d . . . H37 H 1.0255 0.3022 1.1765 0.079 Uiso 1 1 calc R . . C38 C 1.0362(5) 0.3612(5) 1.0219(4) 0.0534(10) Uani 1 1 d . . . H38 H 0.9365 0.2882 0.9492 0.064 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 0.0276(13) 0.0506(16) 0.0597(16) 0.0150(13) 0.0254(12) 0.0113(11) O2 0.0641(18) 0.0297(14) 0.0556(17) 0.0153(13) 0.0205(15) 0.0151(13) O3 0.0244(12) 0.0420(15) 0.0606(17) 0.0109(13) 0.0187(12) 0.0112(11) O4 0.0606(19) 0.0376(16) 0.062(2) 0.0161(15) 0.0059(15) 0.0026(14) N1 0.0249(15) 0.0377(17) 0.0494(18) 0.0011(14) 0.0158(14) 0.0109(13) N2 0.086(3) 0.0324(18) 0.0449(19) 0.0163(16) 0.0281(18) 0.0203(17) N3 0.0228(14) 0.0347(15) 0.0411(16) 0.0096(13) 0.0165(12) 0.0091(12) N4 0.075(3) 0.046(2) 0.047(2) 0.0158(18) 0.0030(18) 0.0060(18) C1 0.0255(18) 0.0346(19) 0.040(2) 0.0147(17) 0.0135(16) 0.0066(15) C2 0.0224(16) 0.0274(17) 0.0403(18) 0.0126(15) 0.0136(14) 0.0061(13) C3 0.0341(19) 0.032(2) 0.049(2) 0.0159(17) 0.0159(17) 0.0057(15) C4 0.076(3) 0.057(3) 0.058(3) 0.030(2) 0.026(2) 0.019(2) C5 0.0332(18) 0.0317(18) 0.045(2) 0.0151(16) 0.0150(16) 0.0097(15) C6 0.033(2) 0.052(2) 0.051(2) 0.002(2) 0.0113(18) 0.0148(18) C7 0.160(6) 0.059(3) 0.058(3) 0.009(3) 0.017(3) 0.060(4) C8 0.0348(19) 0.041(2) 0.045(2) 0.0205(18) 0.0161(16) 0.0124(16) C9 0.049(2) 0.055(3) 0.091(3) 0.044(3) 0.039(2) 0.026(2) C10 0.050(3) 0.071(3) 0.115(4) 0.059(3) 0.042(3) 0.021(2) C11 0.060(3) 0.049(3) 0.079(3) 0.042(2) 0.027(2) 0.016(2) C12 0.052(3) 0.049(2) 0.065(3) 0.035(2) 0.026(2) 0.025(2) C13 0.039(2) 0.043(2) 0.055(2) 0.0239(19) 0.0199(18) 0.0168(18) C14 0.038(2) 0.041(2) 0.049(2) 0.0054(18) 0.0254(18) 0.0143(17) C15 0.044(2) 0.056(3) 0.050(3) 0.002(2) 0.015(2) 0.008(2) C16 0.056(3) 0.090(4) 0.072(4) -0.004(3) 0.011(3) 0.024(3) C17 0.107(5) 0.108(6) 0.054(3) 0.005(4) 0.017(3) 0.074(5) C18 0.190(8) 0.114(6) 0.092(5) 0.066(5) 0.093(6) 0.106(6) C19 0.092(4) 0.065(3) 0.078(4) 0.032(3) 0.053(3) 0.032(3) C20 0.0263(18) 0.0348(19) 0.0367(19) 0.0149(16) 0.0134(15) 0.0118(15) C21 0.0273(17) 0.0380(19) 0.0360(19) 0.0107(16) 0.0141(15) 0.0108(15) C22 0.0351(19) 0.0328(19) 0.049(2) 0.0120(17) 0.0116(17) 0.0055(15) C23 0.065(3) 0.059(3) 0.060(3) 0.034(2) 0.021(2) 0.017(2) C24 0.038(2) 0.042(2) 0.036(2) 0.0103(17) 0.0133(16) 0.0114(17) C25 0.0307(18) 0.0306(18) 0.045(2) 0.0096(16) 0.0212(16) 0.0066(15) C26 0.057(2) 0.038(2) 0.060(3) 0.017(2) 0.029(2) 0.0160(19) C27 0.048(2) 0.048(2) 0.0343(19) 0.0175(18) 0.0188(17) 0.0196(18) C28 0.062(3) 0.073(3) 0.066(3) 0.038(3) 0.025(2) 0.033(2) C29 0.099(4) 0.093(4) 0.070(3) 0.051(3) 0.043(3) 0.067(4) C30 0.132(5) 0.055(3) 0.068(3) 0.037(3) 0.054(3) 0.042(3) C31 0.103(4) 0.055(3) 0.082(4) 0.040(3) 0.058(3) 0.031(3) C32 0.067(3) 0.059(3) 0.060(3) 0.030(2) 0.042(2) 0.028(2) C33 0.0343(19) 0.038(2) 0.041(2) 0.0097(17) 0.0214(16) 0.0114(15) C34 0.035(2) 0.049(2) 0.053(3) 0.0087(19) 0.0214(19) -0.0010(18) C35 0.042(2) 0.079(3) 0.041(2) 0.006(2) 0.013(2) 0.007(2) C36 0.070(3) 0.073(3) 0.044(2) 0.019(2) 0.022(2) 0.023(3) C37 0.077(3) 0.058(3) 0.053(3) 0.023(2) 0.033(2) 0.004(2) C38 0.047(2) 0.048(2) 0.042(2) 0.0108(19) 0.0154(18) -0.0049(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.236(4) . ? O2 C3 1.419(4) . ? O3 C20 1.234(4) . ? O4 C22 1.432(4) . ? N1 C1 1.333(4) . ? N1 C6 1.459(5) . ? N2 C5 1.474(5) . ? N3 C20 1.331(4) . ? N3 C25 1.456(4) . ? N4 C24 1.466(5) . ? C1 C2 1.506(4) . ? C2 C3 1.546(4) . ? C2 C5 1.549(5) . ? C3 C4 1.512(5) . ? C5 C8 1.513(5) . ? C6 C14 1.503(6) . ? C6 C7 1.527(7) . ? C8 C9 1.384(5) . ? C8 C13 1.387(5) . ? C9 C10 1.379(6) . ? C10 C11 1.376(6) . ? C11 C12 1.367(6) . ? C12 C13 1.372(5) . ? C14 C19 1.373(6) . ? C14 C15 1.386(6) . ? C15 C16 1.348(7) . ? C16 C17 1.293(9) . ? C17 C18 1.385(10) . ? C18 C19 1.422(10) . ? C20 C21 1.515(5) . ? C21 C22 1.521(5) . ? C21 C24 1.560(5) . ? C22 C23 1.510(5) . ? C24 C27 1.518(5) . ? C25 C33 1.519(5) . ? C25 C26 1.524(5) . ? C27 C32 1.364(6) . ? C27 C28 1.388(5) . ? C28 C29 1.402(7) . ? C29 C30 1.362(7) . ? C30 C31 1.358(7) . ? C31 C32 1.385(6) . ? C33 C34 1.372(5) . ? C33 C38 1.388(5) . ? C34 C35 1.369(6) . ? C35 C36 1.379(6) . ? C36 C37 1.369(7) . ? C37 C38 1.377(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C6 123.7(3) . . ? C20 N3 C25 122.8(3) . . ? O1 C1 N1 122.0(3) . . ? O1 C1 C2 121.3(3) . . ? N1 C1 C2 116.7(3) . . ? C1 C2 C3 110.2(2) . . ? C1 C2 C5 107.1(2) . . ? C3 C2 C5 112.9(3) . . ? O2 C3 C4 106.9(3) . . ? O2 C3 C2 111.2(3) . . ? C4 C3 C2 111.8(3) . . ? N2 C5 C8 112.8(3) . . ? N2 C5 C2 110.0(3) . . ? C8 C5 C2 111.3(3) . . ? N1 C6 C14 109.8(3) . . ? N1 C6 C7 108.7(3) . . ? C14 C6 C7 115.1(4) . . ? C9 C8 C13 117.2(3) . . ? C9 C8 C5 121.4(3) . . ? C13 C8 C5 121.4(3) . . ? C10 C9 C8 120.9(4) . . ? C11 C10 C9 120.8(4) . . ? C12 C11 C10 119.0(4) . . ? C11 C12 C13 120.3(4) . . ? C12 C13 C8 121.9(3) . . ? C19 C14 C15 117.0(4) . . ? C19 C14 C6 120.5(4) . . ? C15 C14 C6 122.5(4) . . ? C16 C15 C14 122.1(5) . . ? C17 C16 C15 121.3(6) . . ? C16 C17 C18 121.7(6) . . ? C17 C18 C19 117.5(5) . . ? C14 C19 C18 120.4(6) . . ? O3 C20 N3 122.0(3) . . ? O3 C20 C21 120.7(3) . . ? N3 C20 C21 117.2(3) . . ? C20 C21 C22 109.6(3) . . ? C20 C21 C24 107.2(3) . . ? C22 C21 C24 113.4(3) . . ? O4 C22 C23 106.4(3) . . ? O4 C22 C21 111.7(3) . . ? C23 C22 C21 112.1(3) . . ? N4 C24 C27 114.7(3) . . ? N4 C24 C21 109.5(3) . . ? C27 C24 C21 110.1(3) . . ? N3 C25 C33 112.6(3) . . ? N3 C25 C26 109.2(3) . . ? C33 C25 C26 111.6(3) . . ? C32 C27 C28 118.3(4) . . ? C32 C27 C24 120.8(3) . . ? C28 C27 C24 120.7(4) . . ? C27 C28 C29 119.8(5) . . ? C30 C29 C28 120.0(4) . . ? C31 C30 C29 120.6(4) . . ? C30 C31 C32 119.4(5) . . ? C27 C32 C31 121.8(4) . . ? C34 C33 C38 118.1(3) . . ? C34 C33 C25 120.8(3) . . ? C38 C33 C25 121.1(3) . . ? C35 C34 C33 122.2(4) . . ? C34 C35 C36 119.1(4) . . ? C37 C36 C35 119.9(4) . . ? C36 C37 C38 120.5(4) . . ? C37 C38 C33 120.3(4) . . ? 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 C6 N1 C1 O1 9.1(5) . . . . ? C6 N1 C1 C2 -169.8(3) . . . . ? O1 C1 C2 C3 59.3(4) . . . . ? N1 C1 C2 C3 -121.9(3) . . . . ? O1 C1 C2 C5 -63.9(4) . . . . ? N1 C1 C2 C5 115.0(3) . . . . ? C1 C2 C3 O2 176.6(3) . . . . ? C5 C2 C3 O2 -63.7(3) . . . . ? C1 C2 C3 C4 57.2(4) . . . . ? C5 C2 C3 C4 176.9(3) . . . . ? C1 C2 C5 N2 179.4(3) . . . . ? C3 C2 C5 N2 58.0(3) . . . . ? C1 C2 C5 C8 -54.9(3) . . . . ? C3 C2 C5 C8 -176.3(3) . . . . ? C1 N1 C6 C14 -136.3(4) . . . . ? C1 N1 C6 C7 97.0(5) . . . . ? N2 C5 C8 C9 59.1(5) . . . . ? C2 C5 C8 C9 -65.0(4) . . . . ? N2 C5 C8 C13 -122.9(4) . . . . ? C2 C5 C8 C13 112.9(4) . . . . ? C13 C8 C9 C10 -0.6(6) . . . . ? C5 C8 C9 C10 177.4(4) . . . . ? C8 C9 C10 C11 0.1(7) . . . . ? C9 C10 C11 C12 0.8(7) . . . . ? C10 C11 C12 C13 -1.2(7) . . . . ? C11 C12 C13 C8 0.6(6) . . . . ? C9 C8 C13 C12 0.3(6) . . . . ? C5 C8 C13 C12 -177.7(3) . . . . ? N1 C6 C14 C19 62.1(5) . . . . ? C7 C6 C14 C19 -174.9(4) . . . . ? N1 C6 C14 C15 -118.8(4) . . . . ? C7 C6 C14 C15 4.2(6) . . . . ? C19 C14 C15 C16 -1.7(6) . . . . ? C6 C14 C15 C16 179.1(4) . . . . ? C14 C15 C16 C17 1.3(8) . . . . ? C15 C16 C17 C18 0.3(9) . . . . ? C16 C17 C18 C19 -1.3(9) . . . . ? C15 C14 C19 C18 0.6(6) . . . . ? C6 C14 C19 C18 179.8(4) . . . . ? C17 C18 C19 C14 0.8(7) . . . . ? C25 N3 C20 O3 3.7(5) . . . . ? C25 N3 C20 C21 -174.6(3) . . . . ? O3 C20 C21 C22 51.9(4) . . . . ? N3 C20 C21 C22 -129.8(3) . . . . ? O3 C20 C21 C24 -71.6(4) . . . . ? N3 C20 C21 C24 106.7(3) . . . . ? C20 C21 C22 O4 -179.8(3) . . . . ? C24 C21 C22 O4 -60.0(4) . . . . ? C20 C21 C22 C23 60.9(4) . . . . ? C24 C21 C22 C23 -179.4(3) . . . . ? C20 C21 C24 N4 -177.5(3) . . . . ? C22 C21 C24 N4 61.3(4) . . . . ? C20 C21 C24 C27 -50.5(4) . . . . ? C22 C21 C24 C27 -171.7(3) . . . . ? C20 N3 C25 C33 -92.4(3) . . . . ? C20 N3 C25 C26 143.1(3) . . . . ? N4 C24 C27 C32 -136.4(4) . . . . ? C21 C24 C27 C32 99.5(4) . . . . ? N4 C24 C27 C28 48.6(5) . . . . ? C21 C24 C27 C28 -75.5(4) . . . . ? C32 C27 C28 C29 -0.7(6) . . . . ? C24 C27 C28 C29 174.4(4) . . . . ? C27 C28 C29 C30 0.1(7) . . . . ? C28 C29 C30 C31 0.2(7) . . . . ? C29 C30 C31 C32 0.1(7) . . . . ? C28 C27 C32 C31 1.1(6) . . . . ? C24 C27 C32 C31 -174.0(4) . . . . ? C30 C31 C32 C27 -0.8(7) . . . . ? N3 C25 C33 C34 161.8(3) . . . . ? C26 C25 C33 C34 -74.9(4) . . . . ? N3 C25 C33 C38 -18.5(4) . . . . ? C26 C25 C33 C38 104.8(4) . . . . ? C38 C33 C34 C35 1.0(6) . . . . ? C25 C33 C34 C35 -179.3(4) . . . . ? C33 C34 C35 C36 -0.5(6) . . . . ? C34 C35 C36 C37 -1.3(7) . . . . ? C35 C36 C37 C38 2.4(7) . . . . ? C36 C37 C38 C33 -1.9(7) . . . . ? C34 C33 C38 C37 0.1(6) . . . . ? C25 C33 C38 C37 -179.5(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 O4 H4 N4 0.84 1.95 2.701(4) 148.7 . N3 H3 O1 0.88 2.03 2.884(3) 163.1 . N1 H1 O3 0.88 2.01 2.877(3) 167.8 1_455 O2 H2 N2 0.84 1.96 2.698(4) 146.8 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.249 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.036