####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_apsii57 _database_code_depnum_ccdc_archive 'CCDC 668136' _audit_creation_date 2007-09-11T13:24:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #---------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H40 N4 O6' _chemical_formula_sum 'C26 H40 N4 O6' _chemical_formula_weight 504.62 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3903(7) _cell_length_b 16.0688(10) _cell_length_c 19.4462(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2934.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7886 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 20.816 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0794 _diffrn_reflns_number 7886 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 20.66 _diffrn_reflns_theta_full 20.66 _diffrn_measured_fraction_theta_full 0.951 _diffrn_measured_fraction_theta_max 0.951 _reflns_number_total 1660 _reflns_number_gt 1038 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. Because the ratio of reflections used in the refinement to refined parameters is less than 6, restrained anisotropic displacement parameters (DELU and SIMU) were employed from the start for all non-H atoms. ; _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^)+(0.0488P)^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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0092(17) _refine_ls_number_reflns 1660 _refine_ls_number_parameters 326 _refine_ls_number_restraints 313 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.915 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.103 _refine_diff_density_min -0.14 _refine_diff_density_rms 0.03 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.0724(7) 0.1177(4) 1.0421(4) 0.0724(18) Uani 1 1 d U . . C2 C 0.0072(7) 0.0666(4) 1.1006(3) 0.091(2) Uani 1 1 d U . . H2A H -0.0864 0.0485 1.0875 0.136 Uiso 1 1 calc R . . H2B H 0.001 0.1003 1.1412 0.136 Uiso 1 1 calc R . . H2C H 0.066 0.019 1.1096 0.136 Uiso 1 1 calc R . . C3 C -0.0254(7) 0.1900(4) 1.0241(4) 0.100(2) Uani 1 1 d U . . H3A H -0.1179 0.169 1.0122 0.15 Uiso 1 1 calc R . . H3B H 0.0134 0.22 0.9858 0.15 Uiso 1 1 calc R . . H3C H -0.0335 0.2265 1.063 0.15 Uiso 1 1 calc R . . C4 C 0.2189(7) 0.1471(5) 1.0619(4) 0.123(3) Uani 1 1 d U . . H4A H 0.2586 0.1791 1.0249 0.185 Uiso 1 1 calc R . . H4B H 0.2787 0.0998 1.0709 0.185 Uiso 1 1 calc R . . H4C H 0.2128 0.1809 1.1024 0.185 Uiso 1 1 calc R . . O1 O 0.0782(4) 0.0585(2) 0.9855(2) 0.0700(12) Uani 1 1 d U . . C5 C 0.1384(7) 0.0783(5) 0.9248(4) 0.074(2) Uani 1 1 d U . . O2 O 0.1905(5) 0.1457(3) 0.9118(2) 0.0963(16) Uani 1 1 d U . . N1 N 0.1307(5) 0.0151(4) 0.8810(3) 0.0667(14) Uani 1 1 d U . . C6 C 0.0584(6) -0.0632(4) 0.8948(3) 0.0622(16) Uani 1 1 d U . . H6 H -0.0402 -0.0532 0.9091 0.075 Uiso 1 1 calc R . . C7 C 0.0629(7) -0.1058(4) 0.8233(3) 0.098(2) Uani 1 1 d U . . H7A H 0.0755 -0.1654 0.828 0.118 Uiso 1 1 calc R . . H7B H -0.0243 -0.0952 0.798 0.118 Uiso 1 1 calc R . . C8 C 0.1896(8) -0.0669(5) 0.7873(4) 0.102(2) Uani 1 1 d U . . H8A H 0.277 -0.0954 0.7997 0.123 Uiso 1 1 calc R . . H8B H 0.1779 -0.0692 0.7378 0.123 Uiso 1 1 calc R . . C9 C 0.1921(7) 0.0208(5) 0.8118(3) 0.088(2) Uani 1 1 d U . . H9A H 0.2886 0.0422 0.8133 0.106 Uiso 1 1 calc R . . H9B H 0.1349 0.0563 0.7824 0.106 Uiso 1 1 calc R . . C10 C 0.1358(7) -0.1147(3) 0.9477(3) 0.0564(16) Uani 1 1 d U . . O3 O 0.2650(4) -0.1190(2) 0.95035(19) 0.0719(13) Uani 1 1 d U . . N2 N 0.0487(4) -0.1593(3) 0.9883(2) 0.0614(14) Uani 1 1 d U . . H2 H -0.0416 -0.153 0.983 0.074 Uiso 1 1 calc R . . C11 C 0.0974(6) -0.2177(4) 1.0406(3) 0.0589(15) Uani 1 1 d U . . H11 H 0.2015 -0.2211 1.0386 0.071 Uiso 1 1 calc R . . C12 C 0.0540(7) -0.1864(3) 1.1120(3) 0.0726(18) Uani 1 1 d U . . H12A H -0.0489 -0.1882 1.1158 0.087 Uiso 1 1 calc R . . H12B H 0.0834 -0.1288 1.1168 0.087 Uiso 1 1 calc R . . C13 C 0.1193(9) -0.2374(5) 1.1707(3) 0.106(2) Uani 1 1 d U . . H13 H 0.1033 -0.2964 1.1607 0.127 Uiso 1 1 calc R . . C14 C 0.2774(9) -0.2236(7) 1.1761(4) 0.200(5) Uani 1 1 d U . . H14A H 0.3218 -0.2375 1.1331 0.3 Uiso 1 1 calc R . . H14B H 0.3156 -0.2582 1.2118 0.3 Uiso 1 1 calc R . . H14C H 0.2957 -0.1662 1.1867 0.3 Uiso 1 1 calc R . . C15 C 0.0445(10) -0.2170(5) 1.2378(4) 0.161(4) Uani 1 1 d U . . H15A H -0.0555 -0.2281 1.2332 0.242 Uiso 1 1 calc R . . H15B H 0.0584 -0.1593 1.2486 0.242 Uiso 1 1 calc R . . H15C H 0.0833 -0.2507 1.274 0.242 Uiso 1 1 calc R . . N3 N 0.0397(5) -0.2982(3) 1.0273(2) 0.0586(14) Uani 1 1 d U . . H3 H -0.0513 -0.3044 1.0277 0.07 Uiso 1 1 calc R . . C16 C 0.1235(7) -0.3659(4) 1.0140(3) 0.0532(16) Uani 1 1 d U . . O4 O 0.2515(4) -0.3629(2) 1.0061(2) 0.0783(14) Uani 1 1 d U . . N4 N 0.0484(5) -0.4376(3) 1.0115(3) 0.0794(17) Uani 1 1 d U . . H4 H -0.0422 -0.4353 1.0177 0.095 Uiso 1 1 calc R . . C17 C 0.1128(7) -0.5178(4) 0.9990(4) 0.0676(17) Uani 1 1 d U . . H17 H 0.2163 -0.5104 1.0008 0.081 Uiso 1 1 calc R . . C18 C 0.0718(7) -0.5801(3) 1.0555(3) 0.0780(19) Uani 1 1 d U . . H18A H -0.0306 -0.5777 1.0619 0.094 Uiso 1 1 calc R . . H18B H 0.0949 -0.6356 1.0395 0.094 Uiso 1 1 calc R . . C19 C 0.1417(8) -0.5670(5) 1.1236(4) 0.084(2) Uani 1 1 d DU . . C20 C 0.0972(10) -0.5058(5) 1.1673(5) 0.125(3) Uani 1 1 d DU . . H20 H 0.0231 -0.4708 1.1542 0.15 Uiso 1 1 calc R . . C21 C 0.1604(14) -0.4953(7) 1.2304(6) 0.173(5) Uani 1 1 d DU . . H21 H 0.1281 -0.4531 1.2592 0.208 Uiso 1 1 calc R . . C22 C 0.2673(15) -0.5441(9) 1.2516(7) 0.180(6) Uani 1 1 d DU . . H22 H 0.3087 -0.5365 1.2946 0.216 Uiso 1 1 calc R . . C23 C 0.3144(10) -0.6061(7) 1.2078(5) 0.151(4) Uani 1 1 d DU . . H23 H 0.3881 -0.6412 1.2212 0.181 Uiso 1 1 calc R . . C24 C 0.2513(9) -0.6155(5) 1.1440(4) 0.107(3) Uani 1 1 d DU . . H24 H 0.2853 -0.6563 1.1143 0.129 Uiso 1 1 calc R . . C25 C 0.0756(7) -0.5495(5) 0.9282(4) 0.0753(19) Uani 1 1 d U . . O5 O 0.0056(6) -0.5146(3) 0.8861(3) 0.1103(19) Uani 1 1 d U . . O6 O 0.1302(4) -0.6244(3) 0.9179(2) 0.0852(14) Uani 1 1 d U . . C26 C 0.1039(8) -0.6646(4) 0.8525(3) 0.100(2) Uani 1 1 d U . . H26A H 0.1487 -0.7183 0.8521 0.15 Uiso 1 1 calc R . . H26B H 0.1424 -0.6311 0.8161 0.15 Uiso 1 1 calc R . . H26C H 0.0032 -0.6711 0.8459 0.15 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 0.074(5) 0.061(4) 0.082(5) -0.005(4) -0.001(4) -0.007(4) C2 0.118(5) 0.081(5) 0.073(5) 0.001(4) 0.007(4) -0.005(4) C3 0.120(6) 0.064(4) 0.116(7) 0.008(4) 0.012(5) 0.022(4) C4 0.085(5) 0.144(7) 0.141(7) -0.027(6) -0.011(5) -0.026(5) O1 0.078(3) 0.054(3) 0.078(3) -0.002(2) 0.010(2) -0.010(2) C5 0.070(5) 0.061(5) 0.091(5) 0.012(4) 0.006(4) -0.003(4) O2 0.112(4) 0.056(3) 0.121(4) 0.017(3) 0.024(3) -0.017(3) N1 0.064(4) 0.067(4) 0.069(4) 0.016(3) 0.003(3) -0.001(3) C6 0.052(4) 0.060(4) 0.075(4) 0.005(3) -0.011(3) 0.000(3) C7 0.099(6) 0.109(6) 0.087(5) -0.014(4) -0.016(4) -0.026(4) C8 0.113(6) 0.111(6) 0.083(5) -0.022(5) 0.007(4) -0.016(5) C9 0.084(5) 0.100(5) 0.082(5) 0.014(4) 0.015(4) -0.002(4) C10 0.041(4) 0.045(4) 0.083(4) -0.005(3) -0.005(3) -0.004(3) O3 0.034(2) 0.069(3) 0.113(3) 0.022(3) 0.001(2) -0.001(2) N2 0.034(3) 0.062(3) 0.088(4) 0.015(3) -0.011(3) -0.003(2) C11 0.046(4) 0.050(4) 0.081(4) 0.003(3) -0.007(3) 0.003(3) C12 0.087(5) 0.048(4) 0.082(4) -0.004(3) -0.016(4) 0.011(4) C13 0.147(7) 0.103(6) 0.068(4) -0.010(4) -0.013(5) 0.036(5) C14 0.136(6) 0.334(15) 0.131(8) -0.019(9) -0.051(6) 0.114(8) C15 0.217(9) 0.186(9) 0.081(5) 0.002(6) 0.005(6) 0.066(8) N3 0.038(3) 0.039(3) 0.099(4) 0.000(3) 0.001(3) -0.003(2) C16 0.040(4) 0.047(3) 0.073(4) 0.006(3) 0.000(3) -0.003(3) O4 0.032(2) 0.064(3) 0.139(4) -0.007(3) 0.014(3) 0.000(2) N4 0.042(3) 0.050(3) 0.146(5) -0.017(3) 0.018(3) -0.002(3) C17 0.055(4) 0.043(3) 0.105(5) -0.005(3) 0.011(4) -0.005(3) C18 0.088(5) 0.053(4) 0.093(5) -0.012(3) 0.017(4) -0.020(4) C19 0.095(6) 0.079(6) 0.079(5) -0.023(4) 0.026(4) -0.021(4) C20 0.145(7) 0.105(7) 0.125(7) -0.042(5) 0.049(6) -0.035(5) C21 0.244(14) 0.173(11) 0.102(8) -0.065(8) 0.055(8) -0.087(8) C22 0.222(13) 0.223(15) 0.095(8) -0.034(7) -0.004(8) -0.124(9) C23 0.142(7) 0.196(10) 0.115(8) 0.009(7) -0.025(6) -0.067(7) C24 0.113(7) 0.127(7) 0.082(5) -0.002(5) 0.010(4) -0.019(5) C25 0.070(5) 0.060(5) 0.096(5) 0.001(4) 0.014(4) 0.001(4) O5 0.144(5) 0.079(4) 0.108(4) 0.010(3) -0.007(3) 0.032(3) O6 0.097(3) 0.067(3) 0.092(3) -0.012(3) -0.009(3) 0.020(3) C26 0.135(6) 0.088(5) 0.077(5) -0.023(4) 0.008(5) 0.007(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.457(6) . ? C1 C4 1.504(8) . ? C1 C3 1.522(8) . ? C1 C2 1.530(7) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? O1 C5 1.347(7) . ? C5 O2 1.215(7) . ? C5 N1 1.327(7) . ? N1 C6 1.455(7) . ? N1 C9 1.466(7) . ? C6 C10 1.507(7) . ? C6 C7 1.550(7) . ? C6 H6 0.98 . ? C7 C8 1.516(8) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.487(8) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 O3 1.216(6) . ? C10 N2 1.344(7) . ? N2 C11 1.458(7) . ? N2 H2 0.86 . ? C11 N3 1.426(7) . ? C11 C12 1.531(7) . ? C11 H11 0.98 . ? C12 C13 1.533(8) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.505(10) . ? C13 C15 1.518(9) . ? C13 H13 0.98 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? N3 C16 1.367(6) . ? N3 H3 0.86 . ? C16 O4 1.213(6) . ? C16 N4 1.352(6) . ? N4 C17 1.444(6) . ? N4 H4 0.86 . ? C17 C25 1.510(8) . ? C17 C18 1.535(8) . ? C17 H17 0.98 . ? C18 C19 1.493(9) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C19 C24 1.351(9) . ? C19 C20 1.365(9) . ? C20 C21 1.374(12) . ? C20 H20 0.93 . ? C21 C22 1.339(14) . ? C21 H21 0.93 . ? C22 C23 1.384(14) . ? C22 H22 0.93 . ? C23 C24 1.384(10) . ? C23 H23 0.93 . ? C24 H24 0.93 . ? C25 O5 1.190(7) . ? C25 O6 1.324(7) . ? O6 C26 1.448(6) . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? 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 C4 111.3(5) . . ? O1 C1 C3 110.3(5) . . ? C4 C1 C3 111.8(6) . . ? O1 C1 C2 103.1(5) . . ? C4 C1 C2 110.2(6) . . ? C3 C1 C2 109.8(6) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O1 C1 121.6(5) . . ? O2 C5 N1 124.7(8) . . ? O2 C5 O1 124.2(7) . . ? N1 C5 O1 111.1(6) . . ? C5 N1 C6 124.6(6) . . ? C5 N1 C9 121.4(6) . . ? C6 N1 C9 114.0(6) . . ? N1 C6 C10 112.1(5) . . ? N1 C6 C7 101.7(5) . . ? C10 C6 C7 110.9(5) . . ? N1 C6 H6 110.6 . . ? C10 C6 H6 110.6 . . ? C7 C6 H6 110.6 . . ? C8 C7 C6 104.7(5) . . ? C8 C7 H7A 110.8 . . ? C6 C7 H7A 110.8 . . ? C8 C7 H7B 110.8 . . ? C6 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? C9 C8 C7 104.8(6) . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? N1 C9 C8 103.2(6) . . ? N1 C9 H9A 111.1 . . ? C8 C9 H9A 111.1 . . ? N1 C9 H9B 111.1 . . ? C8 C9 H9B 111.1 . . ? H9A C9 H9B 109.1 . . ? O3 C10 N2 123.6(6) . . ? O3 C10 C6 122.7(6) . . ? N2 C10 C6 113.6(5) . . ? C10 N2 C11 124.2(5) . . ? C10 N2 H2 117.9 . . ? C11 N2 H2 117.9 . . ? N3 C11 N2 109.8(5) . . ? N3 C11 C12 111.2(5) . . ? N2 C11 C12 109.7(5) . . ? N3 C11 H11 108.7 . . ? N2 C11 H11 108.7 . . ? C12 C11 H11 108.7 . . ? C11 C12 C13 113.1(5) . . ? C11 C12 H12A 109 . . ? C13 C12 H12A 109 . . ? C11 C12 H12B 109 . . ? C13 C12 H12B 109 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C15 111.4(7) . . ? C14 C13 C12 111.6(7) . . ? C15 C13 C12 109.9(6) . . ? C14 C13 H13 108 . . ? C15 C13 H13 108 . . ? C12 C13 H13 108 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C16 N3 C11 122.5(5) . . ? C16 N3 H3 118.7 . . ? C11 N3 H3 118.7 . . ? O4 C16 N4 123.2(6) . . ? O4 C16 N3 124.2(6) . . ? N4 C16 N3 112.6(5) . . ? C16 N4 C17 123.2(5) . . ? C16 N4 H4 118.4 . . ? C17 N4 H4 118.4 . . ? N4 C17 C25 111.0(6) . . ? N4 C17 C18 110.9(5) . . ? C25 C17 C18 112.0(5) . . ? N4 C17 H17 107.6 . . ? C25 C17 H17 107.6 . . ? C18 C17 H17 107.6 . . ? C19 C18 C17 115.6(5) . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18B 108.4 . . ? C17 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? C24 C19 C20 117.8(8) . . ? C24 C19 C18 120.9(7) . . ? C20 C19 C18 121.3(9) . . ? C19 C20 C21 120.8(11) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 121.8(14) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 118.1(14) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C22 C23 C24 119.6(12) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C19 C24 C23 121.8(9) . . ? C19 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? O5 C25 O6 122.5(7) . . ? O5 C25 C17 126.6(7) . . ? O6 C25 C17 110.8(6) . . ? C25 O6 C26 118.2(5) . . ? O6 C26 H26A 109.5 . . ? O6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C1 O1 C5 -57.6(8) . . . . ? C3 C1 O1 C5 67.1(7) . . . . ? C2 C1 O1 C5 -175.7(5) . . . . ? C1 O1 C5 O2 -0.8(10) . . . . ? C1 O1 C5 N1 -179.7(5) . . . . ? O2 C5 N1 C6 -175.0(6) . . . . ? O1 C5 N1 C6 3.9(8) . . . . ? O2 C5 N1 C9 2.6(10) . . . . ? O1 C5 N1 C9 -178.5(5) . . . . ? C5 N1 C6 C10 -70.2(7) . . . . ? C9 N1 C6 C10 112.1(6) . . . . ? C5 N1 C6 C7 171.3(6) . . . . ? C9 N1 C6 C7 -6.5(6) . . . . ? N1 C6 C7 C8 24.8(6) . . . . ? C10 C6 C7 C8 -94.6(6) . . . . ? C6 C7 C8 C9 -34.6(7) . . . . ? C5 N1 C9 C8 167.5(6) . . . . ? C6 N1 C9 C8 -14.6(7) . . . . ? C7 C8 C9 N1 29.9(7) . . . . ? N1 C6 C10 O3 -38.3(8) . . . . ? C7 C6 C10 O3 74.7(7) . . . . ? N1 C6 C10 N2 146.0(5) . . . . ? C7 C6 C10 N2 -101.1(6) . . . . ? O3 C10 N2 C11 0.5(9) . . . . ? C6 C10 N2 C11 176.2(5) . . . . ? C10 N2 C11 N3 -122.5(6) . . . . ? C10 N2 C11 C12 115.0(6) . . . . ? N3 C11 C12 C13 66.6(7) . . . . ? N2 C11 C12 C13 -171.7(6) . . . . ? C11 C12 C13 C14 69.8(8) . . . . ? C11 C12 C13 C15 -166.1(6) . . . . ? N2 C11 N3 C16 118.5(5) . . . . ? C12 C11 N3 C16 -119.9(6) . . . . ? C11 N3 C16 O4 -7.0(9) . . . . ? C11 N3 C16 N4 172.1(5) . . . . ? O4 C16 N4 C17 -0.2(10) . . . . ? N3 C16 N4 C17 -179.3(6) . . . . ? C16 N4 C17 C25 -108.3(7) . . . . ? C16 N4 C17 C18 126.6(6) . . . . ? N4 C17 C18 C19 -73.1(7) . . . . ? C25 C17 C18 C19 162.3(6) . . . . ? C17 C18 C19 C24 -102.9(8) . . . . ? C17 C18 C19 C20 77.1(8) . . . . ? C24 C19 C20 C21 -1.2(10) . . . . ? C18 C19 C20 C21 178.7(7) . . . . ? C19 C20 C21 C22 0.0(15) . . . . ? C20 C21 C22 C23 0.4(19) . . . . ? C21 C22 C23 C24 0.4(18) . . . . ? C20 C19 C24 C23 2.1(11) . . . . ? C18 C19 C24 C23 -177.9(7) . . . . ? C22 C23 C24 C19 -1.8(14) . . . . ? N4 C17 C25 O5 1.4(10) . . . . ? C18 C17 C25 O5 126.0(8) . . . . ? N4 C17 C25 O6 -177.6(5) . . . . ? C18 C17 C25 O6 -53.0(7) . . . . ? O5 C25 O6 C26 0.5(10) . . . . ? C17 C25 O6 C26 179.5(5) . . . . ? 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 N3 H3 O3 0.86 2.16 2.934(6) 149.3 3_447 N2 H2 O4 0.86 1.97 2.815(6) 167 3_447 N4 H4 O3 0.86 2.1 2.908(6) 155.5 3_447 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 668137' _audit_creation_date 2007-04-26T13:51:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H27 N3 O3' _chemical_formula_sum 'C17 H27 N3 O3' _chemical_formula_weight 321.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.2410(10) _cell_length_b 17.883(3) _cell_length_c 19.356(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1814.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.56 _cell_measurement_theta_max 42.08 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5406 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0063 _diffrn_reflns_number 2026 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 69.83 _diffrn_reflns_theta_full 69.83 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2026 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. The 1 methylene, 3 methyl, urea group was found to be disordered. It was built over two sites (refined occupancy factors 0.490(8)/0.510(8)). The bond distances of both urea groups modelled were restrained ; _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^)+(0.1030P)^2^+0.1310P] 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_number_reflns 2026 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.272 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.4447(5) 0.08065(12) -0.17244(11) 0.0510(5) Uani 1 1 d . . . C2 C 0.2670(6) 0.12478(17) -0.21970(15) 0.0719(8) Uani 1 1 d . . . H2A H 0.1614 0.1572 -0.1924 0.108 Uiso 1 1 calc R . . H2B H 0.1612 0.0907 -0.2452 0.108 Uiso 1 1 calc R . . H2C H 0.3664 0.1542 -0.2513 0.108 Uiso 1 1 calc R . . C3 C 0.5966(7) 0.13305(16) -0.12691(15) 0.0727(8) Uani 1 1 d . . . H3A H 0.4818 0.1641 -0.101 0.109 Uiso 1 1 calc R . . H3B H 0.7043 0.1639 -0.1552 0.109 Uiso 1 1 calc R . . H3C H 0.6999 0.1044 -0.0957 0.109 Uiso 1 1 calc R . . C4 C 0.6110(5) 0.02895(15) -0.21484(13) 0.0649(6) Uani 1 1 d . . . H4A H 0.5051 -0.0031 -0.2424 0.097 Uiso 1 1 calc R . . H4B H 0.7142 -0.0009 -0.1845 0.097 Uiso 1 1 calc R . . H4C H 0.7194 0.0581 -0.2444 0.097 Uiso 1 1 calc R . . O1 O 0.2631(3) 0.03673(9) -0.13114(8) 0.0529(4) Uani 1 1 d . . . C5 C 0.3456(4) -0.00635(12) -0.07779(9) 0.0436(4) Uani 1 1 d . . . O2 O 0.5665(3) -0.01578(11) -0.06191(8) 0.0589(4) Uani 1 1 d . . . N1 N 0.1443(3) -0.03806(10) -0.04728(8) 0.0458(4) Uani 1 1 d . . . H1 H -0.0021 -0.0354 -0.0672 0.055 Uiso 1 1 calc R . . C6 C 0.1646(4) -0.07719(11) 0.01896(9) 0.0444(4) Uani 1 1 d . . . H6 H 0.3451 -0.087 0.0285 0.053 Uiso 1 1 calc R . . C7 C 0.0557(5) -0.02909(13) 0.07734(11) 0.0566(6) Uani 1 1 d . . . H7A H -0.1214 -0.0177 0.0672 0.068 Uiso 1 1 calc R . . H7B H 0.0602 -0.0575 0.12 0.068 Uiso 1 1 calc R . . C8 C 0.1997(5) 0.04296(13) 0.08732(11) 0.0555(6) Uani 1 1 d . . . C9 C 0.4096(6) 0.04647(17) 0.12982(13) 0.0698(7) Uani 1 1 d . . . H9 H 0.4594 0.0038 0.1537 0.084 Uiso 1 1 calc R . . C10 C 0.5485(8) 0.1113(2) 0.13805(18) 0.0920(10) Uani 1 1 d . . . H10 H 0.6897 0.1122 0.1671 0.11 Uiso 1 1 calc R . . C11 C 0.4768(10) 0.1747(2) 0.1029(2) 0.1040(14) Uani 1 1 d . . . H11 H 0.5697 0.2187 0.1081 0.125 Uiso 1 1 calc R . . C12 C 0.2702(10) 0.17309(16) 0.06073(19) 0.0950(12) Uani 1 1 d . . . H12 H 0.2231 0.2162 0.037 0.114 Uiso 1 1 calc R . . C13 C 0.1271(7) 0.10784(14) 0.05225(14) 0.0734(8) Uani 1 1 d . . . H13 H -0.0151 0.1076 0.0235 0.088 Uiso 1 1 calc R . . C14 C 0.0249(6) -0.15183(12) 0.01274(11) 0.0561(6) Uani 1 1 d . . . H14A H -0.1563 -0.1425 0.0073 0.067 Uiso 1 1 calc R . . H14B H 0.084 -0.1776 -0.0284 0.067 Uiso 1 1 calc R . . N2 N 0.0643(5) -0.19976(11) 0.07243(10) 0.0612(5) Uani 1 1 d . . . H2 H 0.2145 -0.2174 0.0799 0.073 Uiso 1 1 calc R . . C15 C -0.1248(5) -0.21765(12) 0.11656(12) 0.0548(6) Uani 1 1 d . . . O3 O -0.3381(4) -0.19157(13) 0.11276(12) 0.0831(6) Uani 1 1 d . . . N3 N -0.0549(6) -0.26824(12) 0.16722(11) 0.0689(6) Uani 1 1 d . . . C16 C -0.2327(10) -0.2876(3) 0.22028(17) 0.1073(14) Uani 1 1 d . . . H16A H -0.1458 -0.2901 0.2639 0.161 Uiso 1 1 calc R . . H16B H -0.3072 -0.3354 0.2101 0.161 Uiso 1 1 calc R . . H16C H -0.3645 -0.2505 0.2225 0.161 Uiso 1 1 calc R . . C17 C 0.1547(10) -0.3175(2) 0.1598(2) 0.1140(15) Uani 1 1 d . . . H17A H 0.1737 -0.3466 0.2012 0.171 Uiso 1 1 calc R . . H17B H 0.3073 -0.2891 0.1519 0.171 Uiso 1 1 calc R . . H17C H 0.1251 -0.3502 0.1213 0.171 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 0.0519(11) 0.0580(11) 0.0431(10) 0.0116(8) 0.0039(10) -0.0067(11) C2 0.0697(16) 0.0787(16) 0.0672(15) 0.0355(13) 0.0030(14) -0.0035(14) C3 0.086(2) 0.0679(13) 0.0637(14) -0.0014(12) -0.0020(16) -0.0162(15) C4 0.0706(15) 0.0744(14) 0.0498(11) 0.0024(10) 0.0113(12) -0.0036(13) O1 0.0470(8) 0.0687(9) 0.0432(7) 0.0212(7) 0.0012(6) -0.0025(8) C5 0.0478(10) 0.0489(9) 0.0342(8) 0.0041(7) 0.0012(8) 0.0039(9) O2 0.0456(8) 0.0798(11) 0.0513(8) 0.0199(8) 0.0020(7) 0.0052(8) N1 0.0451(8) 0.0574(9) 0.0348(8) 0.0115(7) 0.0001(7) -0.0004(8) C6 0.0519(10) 0.0512(9) 0.0301(8) 0.0085(7) 0.0022(8) 0.0041(10) C7 0.0666(14) 0.0630(12) 0.0401(9) -0.0005(8) 0.0141(11) -0.0010(12) C8 0.0686(14) 0.0581(11) 0.0398(9) -0.0058(8) 0.0149(10) 0.0059(12) C9 0.0764(17) 0.0813(16) 0.0517(12) -0.0135(12) 0.0089(13) 0.0034(15) C10 0.086(2) 0.112(2) 0.0773(18) -0.0400(18) 0.0147(19) -0.014(2) C11 0.133(4) 0.077(2) 0.101(2) -0.045(2) 0.045(3) -0.029(2) C12 0.138(3) 0.0539(13) 0.093(2) -0.0105(14) 0.030(3) 0.0065(19) C13 0.095(2) 0.0621(13) 0.0631(14) -0.0038(11) 0.0101(16) 0.0134(15) C14 0.0716(14) 0.0543(10) 0.0423(10) 0.0066(8) 0.0042(11) -0.0041(12) N2 0.0679(12) 0.0598(10) 0.0560(11) 0.0196(9) 0.0093(11) 0.0039(10) C15 0.0728(15) 0.0464(10) 0.0452(10) -0.0015(8) 0.0056(11) -0.0141(10) O3 0.0691(12) 0.0932(14) 0.0871(14) 0.0183(12) 0.0167(12) -0.0035(12) N3 0.1032(17) 0.0563(10) 0.0474(10) 0.0088(8) 0.0078(12) -0.0161(12) C16 0.135(3) 0.122(3) 0.0648(17) 0.0248(18) 0.021(2) -0.034(3) C17 0.133(4) 0.094(2) 0.114(3) 0.052(2) 0.012(3) 0.018(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.470(2) . ? C1 C3 1.513(4) . ? C1 C4 1.513(3) . ? C1 C2 1.526(3) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? O1 C5 1.359(2) . ? C5 O2 1.210(3) . ? C5 N1 1.335(3) . ? N1 C6 1.464(2) . ? N1 H1 0.86 . ? C6 C14 1.527(3) . ? C6 C7 1.531(3) . ? C6 H6 0.98 . ? C7 C8 1.506(3) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.375(4) . ? C8 C13 1.397(3) . ? C9 C10 1.379(5) . ? C9 H9 0.93 . ? C10 C11 1.374(6) . ? C10 H10 0.93 . ? C11 C12 1.356(6) . ? C11 H11 0.93 . ? C12 C13 1.397(5) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 N2 1.453(3) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? N2 C15 1.347(3) . ? N2 H2 0.86 . ? C15 O3 1.214(3) . ? C15 N3 1.383(3) . ? N3 C17 1.415(5) . ? N3 C16 1.430(4) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? 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 C3 110.77(19) . . ? O1 C1 C4 109.97(18) . . ? C3 C1 C4 113.0(2) . . ? O1 C1 C2 102.0(2) . . ? C3 C1 C2 110.5(2) . . ? C4 C1 C2 110.0(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O1 C1 120.68(17) . . ? O2 C5 N1 125.76(18) . . ? O2 C5 O1 125.22(19) . . ? N1 C5 O1 109.00(17) . . ? C5 N1 C6 122.20(18) . . ? C5 N1 H1 118.9 . . ? C6 N1 H1 118.9 . . ? N1 C6 C14 108.30(16) . . ? N1 C6 C7 110.52(17) . . ? C14 C6 C7 111.75(18) . . ? N1 C6 H6 108.7 . . ? C14 C6 H6 108.7 . . ? C7 C6 H6 108.7 . . ? C8 C7 C6 112.86(19) . . ? C8 C7 H7A 109 . . ? C6 C7 H7A 109 . . ? C8 C7 H7B 109 . . ? C6 C7 H7B 109 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 118.1(3) . . ? C9 C8 C7 121.1(2) . . ? C13 C8 C7 120.8(2) . . ? C8 C9 C10 122.0(3) . . ? C8 C9 H9 119 . . ? C10 C9 H9 119 . . ? C11 C10 C9 119.5(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 119.9(3) . . ? C12 C11 H11 120 . . ? C10 C11 H11 120 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 119.4(3) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? N2 C14 C6 112.63(18) . . ? N2 C14 H14A 109.1 . . ? C6 C14 H14A 109.1 . . ? N2 C14 H14B 109.1 . . ? C6 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C15 N2 C14 122.7(2) . . ? C15 N2 H2 118.7 . . ? C14 N2 H2 118.7 . . ? O3 C15 N2 123.2(2) . . ? O3 C15 N3 122.6(2) . . ? N2 C15 N3 114.2(3) . . ? C15 N3 C17 122.7(3) . . ? C15 N3 C16 119.7(3) . . ? C17 N3 C16 115.3(3) . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C3 C1 O1 C5 -56.8(3) . . . . ? C4 C1 O1 C5 68.8(3) . . . . ? C2 C1 O1 C5 -174.4(2) . . . . ? C1 O1 C5 O2 -4.1(3) . . . . ? C1 O1 C5 N1 177.72(18) . . . . ? O2 C5 N1 C6 12.7(3) . . . . ? O1 C5 N1 C6 -169.13(17) . . . . ? C5 N1 C6 C14 -133.0(2) . . . . ? C5 N1 C6 C7 104.3(2) . . . . ? N1 C6 C7 C8 -62.6(3) . . . . ? C14 C6 C7 C8 176.66(19) . . . . ? C6 C7 C8 C9 -87.7(2) . . . . ? C6 C7 C8 C13 90.8(3) . . . . ? C13 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 C10 178.0(2) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C8 -0.7(5) . . . . ? C9 C8 C13 C12 0.8(4) . . . . ? C7 C8 C13 C12 -177.7(3) . . . . ? N1 C6 C14 N2 171.8(2) . . . . ? C7 C6 C14 N2 -66.3(3) . . . . ? C6 C14 N2 C15 112.9(3) . . . . ? C14 N2 C15 O3 -4.9(4) . . . . ? C14 N2 C15 N3 175.45(19) . . . . ? O3 C15 N3 C17 157.9(3) . . . . ? N2 C15 N3 C17 -22.4(4) . . . . ? O3 C15 N3 C16 -4.2(4) . . . . ? N2 C15 N3 C16 175.4(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 O2 0.86 2.29 3.068(3) 150.4 1_455 N2 H2 O3 0.86 2.47 3.231(4) 147.3 1_655 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 668138' _audit_creation_date 2007-09-12T14:20:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H24 N4 O2' _chemical_formula_sum 'C19 H24 N4 O2' _chemical_formula_weight 340.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.675(2) _cell_length_b 9.497(2) _cell_length_c 10.809(3) _cell_angle_alpha 76.78(2) _cell_angle_beta 81.59(3) _cell_angle_gamma 77.55(2) _cell_volume 453.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.84 _cell_measurement_theta_max 22.92 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 182 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.666 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5406 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_unetI/netI 0.0573 _diffrn_reflns_number 3348 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _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 4.22 _diffrn_reflns_theta_max 69.79 _diffrn_reflns_theta_full 69.79 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1723 _reflns_number_gt 1291 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. The disorder of the N-terminal phenyl group has been refined using DELU restraints to make the anisotropic displacement parameters values of the disordered atoms more reasonable. ; _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^)+(0.0326P)^2^+0.1396P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.015(3) _refine_ls_number_reflns 1723 _refine_ls_number_parameters 228 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.172 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.4306(9) 1.2792(5) -0.4171(4) 0.0534(11) Uani 1 1 d . . . C2 C 0.4550(13) 1.4049(7) -0.3822(6) 0.0772(16) Uani 1 1 d . . . H2 H 0.3501 1.429 -0.3075 0.093 Uiso 1 1 calc R . . C3 C 0.6334(15) 1.4965(8) -0.4563(8) 0.098(2) Uani 1 1 d . . . H3 H 0.6472 1.5819 -0.4312 0.118 Uiso 1 1 calc R . . C4 C 0.7862(15) 1.4647(10) -0.5634(8) 0.103(2) Uani 1 1 d . . . H4 H 0.9071 1.5272 -0.6123 0.124 Uiso 1 1 calc R . . C5 C 0.7656(15) 1.3415(10) -0.6009(6) 0.102(2) Uani 1 1 d . . . H5 H 0.8726 1.3196 -0.6759 0.123 Uiso 1 1 calc R . . C6 C 0.5870(12) 1.2473(7) -0.5290(5) 0.0779(16) Uani 1 1 d . . . H6 H 0.5725 1.163 -0.5559 0.093 Uiso 1 1 calc R . . C7 C 0.2348(12) 1.1796(7) -0.3372(5) 0.0727(17) Uani 1 1 d . . . H7A H 0.0461 1.2378 -0.3129 0.087 Uiso 1 1 calc R . . H7B H 0.2008 1.1124 -0.3865 0.087 Uiso 1 1 calc R . . N1 N 0.3699(8) 1.0965(4) -0.2235(3) 0.0537(10) Uani 1 1 d . . . H1 H 0.5555 1.0904 -0.2217 0.064 Uiso 1 1 calc R . . C8 C 0.2145(8) 1.0281(5) -0.1201(4) 0.0431(10) Uani 1 1 d . . . O1 O -0.0512(6) 1.0296(4) -0.1183(3) 0.0538(8) Uani 1 1 d . . . N2 N 0.3710(7) 0.9571(4) -0.0224(3) 0.0538(10) Uani 1 1 d . . . H2A H 0.5574 0.9557 -0.0319 0.065 Uiso 1 1 calc R . . C9 C 0.2421(9) 0.8820(5) 0.0993(4) 0.0472(10) Uani 1 1 d . . . H9 H 0.0671 0.8503 0.0834 0.057 Uiso 1 1 calc R . . C10 C 0.4564(9) 0.7451(5) 0.1566(4) 0.0492(10) Uani 1 1 d U . . H10A H 0.6447 0.7723 0.1569 0.059 Uiso 1 1 calc R . . H10B H 0.383 0.711 0.2447 0.059 Uiso 1 1 calc R . . C11 C 0.5048(10) 0.6191(6) 0.0873(4) 0.0564(11) Uani 1 1 d U . . C12 C 0.700(2) 0.6113(10) -0.0201(7) 0.128(3) Uani 1 1 d U . . H12 H 0.8071 0.6861 -0.053 0.154 Uiso 1 1 calc R . . C13 C 0.739(3) 0.4947(12) -0.0788(9) 0.166(5) Uani 1 1 d U . . H13 H 0.8672 0.4939 -0.1531 0.199 Uiso 1 1 calc R . . C14 C 0.597(2) 0.3797(9) -0.0327(8) 0.115(3) Uani 1 1 d U . . H14 H 0.6254 0.3006 -0.0732 0.138 Uiso 1 1 calc R . . C15 C 0.416(3) 0.3863(10) 0.0726(10) 0.157(4) Uani 1 1 d U . . H15 H 0.3186 0.3087 0.1084 0.188 Uiso 1 1 calc R . . C16 C 0.370(2) 0.5038(8) 0.1302(8) 0.126(3) Uani 1 1 d U . . H16 H 0.2374 0.5039 0.2033 0.151 Uiso 1 1 calc R . . C17 C 0.1428(10) 0.9916(5) 0.1889(4) 0.0546(12) Uani 1 1 d . . . H17A H 0.3136 1.0258 0.2036 0.065 Uiso 1 1 calc R . . H17B H 0.0095 1.0764 0.1469 0.065 Uiso 1 1 calc R . . N3 N -0.0029(7) 0.9309(5) 0.3111(3) 0.0534(10) Uani 1 1 d . . . H3A H -0.1804 0.9177 0.3145 0.064 Uiso 1 1 calc R . . C18 C 0.1279(9) 0.8948(5) 0.4183(4) 0.0461(10) Uani 1 1 d . . . O2 O 0.3877(6) 0.8983(4) 0.4226(3) 0.0604(9) Uani 1 1 d . . . N4 N -0.0480(8) 0.8486(5) 0.5260(3) 0.0574(11) Uani 1 1 d . . . H4A H -0.2265 0.8449 0.5181 0.069 Uiso 1 1 calc R . . C19 C 0.0487(13) 0.8062(7) 0.6512(5) 0.0695(15) Uani 1 1 d . . . H19A H -0.1049 0.8435 0.7112 0.104 Uiso 1 1 calc R . . H19B H 0.2208 0.8459 0.6514 0.104 Uiso 1 1 calc R . . H19C H 0.0951 0.7007 0.6748 0.104 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 0.049(2) 0.060(3) 0.043(2) 0.008(2) -0.0072(18) -0.010(2) C2 0.074(3) 0.081(4) 0.077(4) -0.021(3) 0.014(3) -0.024(3) C3 0.092(4) 0.055(3) 0.139(6) -0.001(4) 0.003(4) -0.023(3) C4 0.081(4) 0.102(6) 0.101(5) 0.036(4) 0.010(4) -0.035(4) C5 0.091(5) 0.134(7) 0.066(4) -0.004(4) 0.032(3) -0.031(5) C6 0.083(4) 0.080(4) 0.066(3) -0.011(3) 0.001(3) -0.015(3) C7 0.070(3) 0.079(4) 0.063(3) 0.027(3) -0.019(3) -0.035(3) N1 0.0357(18) 0.071(3) 0.046(2) 0.0116(18) -0.0023(15) -0.0192(18) C8 0.038(2) 0.052(2) 0.036(2) -0.0011(18) -0.0021(16) -0.0116(18) O1 0.0328(14) 0.076(2) 0.0484(18) 0.0017(15) -0.0027(12) -0.0184(14) N2 0.0343(17) 0.081(3) 0.0412(19) 0.0081(18) 0.0006(14) -0.0246(18) C9 0.037(2) 0.067(3) 0.037(2) -0.0003(19) 0.0049(16) -0.0237(19) C10 0.049(2) 0.060(3) 0.0366(19) -0.0002(18) 0.0017(16) -0.020(2) C11 0.056(2) 0.062(3) 0.048(2) -0.006(2) 0.0021(19) -0.016(2) C12 0.175(8) 0.126(6) 0.099(5) -0.059(5) 0.073(5) -0.081(6) C13 0.236(13) 0.151(9) 0.124(7) -0.093(7) 0.083(7) -0.064(8) C14 0.164(8) 0.081(5) 0.107(5) -0.045(4) -0.031(5) -0.001(5) C15 0.205(11) 0.089(6) 0.187(10) -0.061(6) 0.061(8) -0.072(7) C16 0.160(7) 0.086(5) 0.134(6) -0.045(5) 0.078(6) -0.068(5) C17 0.050(2) 0.056(3) 0.052(3) 0.002(2) 0.002(2) -0.017(2) N3 0.0378(18) 0.082(3) 0.041(2) -0.0119(19) 0.0048(15) -0.0196(19) C18 0.042(2) 0.054(3) 0.046(2) -0.0157(19) 0.0051(18) -0.0167(19) O2 0.0410(17) 0.087(3) 0.0549(19) -0.0100(17) -0.0016(14) -0.0224(17) N4 0.045(2) 0.084(3) 0.041(2) -0.007(2) 0.0065(16) -0.022(2) C19 0.073(3) 0.079(4) 0.054(3) -0.008(3) -0.002(2) -0.017(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.363(8) . ? C1 C6 1.379(7) . ? C1 C7 1.499(6) . ? C2 C3 1.376(8) . ? C2 H2 0.93 . ? C3 C4 1.329(11) . ? C3 H3 0.93 . ? C4 C5 1.349(11) . ? C4 H4 0.93 . ? C5 C6 1.384(9) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 N1 1.449(6) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? N1 C8 1.355(5) . ? N1 H1 0.86 . ? C8 O1 1.237(5) . ? C8 N2 1.339(5) . ? N2 C9 1.458(5) . ? N2 H2A 0.86 . ? C9 C10 1.526(6) . ? C9 C17 1.536(7) . ? C9 H9 0.98 . ? C10 C11 1.512(7) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C16 1.339(8) . ? C11 C12 1.373(7) . ? C12 C13 1.365(12) . ? C12 H12 0.93 . ? C13 C14 1.360(13) . ? C13 H13 0.93 . ? C14 C15 1.319(12) . ? C14 H14 0.93 . ? C15 C16 1.361(11) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? C17 N3 1.449(5) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? N3 C18 1.330(6) . ? N3 H3A 0.86 . ? C18 O2 1.230(5) . ? C18 N4 1.366(5) . ? N4 C19 1.432(6) . ? N4 H4A 0.86 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? 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 C2 C1 C6 118.3(5) . . ? C2 C1 C7 120.9(5) . . ? C6 C1 C7 120.8(5) . . ? C1 C2 C3 120.6(6) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 121.0(7) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.8(6) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.8(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 119.5(6) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N1 C7 C1 110.2(4) . . ? N1 C7 H7A 109.6 . . ? C1 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C1 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C8 N1 C7 122.4(4) . . ? C8 N1 H1 118.8 . . ? C7 N1 H1 118.8 . . ? O1 C8 N2 123.2(4) . . ? O1 C8 N1 121.8(4) . . ? N2 C8 N1 115.1(3) . . ? C8 N2 C9 123.5(3) . . ? C8 N2 H2A 118.3 . . ? C9 N2 H2A 118.3 . . ? N2 C9 C10 111.0(3) . . ? N2 C9 C17 109.0(4) . . ? C10 C9 C17 112.7(3) . . ? N2 C9 H9 108 . . ? C10 C9 H9 108 . . ? C17 C9 H9 108 . . ? C11 C10 C9 114.6(3) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C16 C11 C12 115.3(6) . . ? C16 C11 C10 122.0(5) . . ? C12 C11 C10 122.5(5) . . ? C13 C12 C11 120.5(8) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 122.5(8) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C15 C14 C13 116.5(8) . . ? C15 C14 H14 121.7 . . ? C13 C14 H14 121.7 . . ? C14 C15 C16 121.6(8) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 123.5(7) . . ? C11 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? N3 C17 C9 113.8(4) . . ? N3 C17 H17A 108.8 . . ? C9 C17 H17A 108.8 . . ? N3 C17 H17B 108.8 . . ? C9 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C18 N3 C17 122.4(4) . . ? C18 N3 H3A 118.8 . . ? C17 N3 H3A 118.8 . . ? O2 C18 N3 124.0(4) . . ? O2 C18 N4 121.4(4) . . ? N3 C18 N4 114.6(4) . . ? C18 N4 C19 123.5(4) . . ? C18 N4 H4A 118.2 . . ? C19 N4 H4A 118.2 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C6 C1 C2 C3 -0.6(9) . . . . ? C7 C1 C2 C3 -179.5(5) . . . . ? C1 C2 C3 C4 -0.1(10) . . . . ? C2 C3 C4 C5 0.5(11) . . . . ? C3 C4 C5 C6 -0.1(12) . . . . ? C2 C1 C6 C5 0.9(8) . . . . ? C7 C1 C6 C5 179.9(6) . . . . ? C4 C5 C6 C1 -0.6(10) . . . . ? C2 C1 C7 N1 -75.1(7) . . . . ? C6 C1 C7 N1 106.0(6) . . . . ? C1 C7 N1 C8 162.5(5) . . . . ? C7 N1 C8 O1 2.0(7) . . . . ? C7 N1 C8 N2 -179.4(5) . . . . ? O1 C8 N2 C9 -4.1(8) . . . . ? N1 C8 N2 C9 177.3(4) . . . . ? C8 N2 C9 C10 146.1(4) . . . . ? C8 N2 C9 C17 -89.2(5) . . . . ? N2 C9 C10 C11 -71.1(5) . . . . ? C17 C9 C10 C11 166.3(3) . . . . ? C9 C10 C11 C16 -100.5(7) . . . . ? C9 C10 C11 C12 82.8(7) . . . . ? C16 C11 C12 C13 2.5(14) . . . . ? C10 C11 C12 C13 179.3(9) . . . . ? C11 C12 C13 C14 -2.3(19) . . . . ? C12 C13 C14 C15 0.3(19) . . . . ? C13 C14 C15 C16 1.5(18) . . . . ? C12 C11 C16 C15 -0.7(15) . . . . ? C10 C11 C16 C15 -177.6(9) . . . . ? C14 C15 C16 C11 -1(2) . . . . ? N2 C9 C17 N3 177.1(4) . . . . ? C10 C9 C17 N3 -59.2(4) . . . . ? C9 C17 N3 C18 105.4(5) . . . . ? C17 N3 C18 O2 -5.9(7) . . . . ? C17 N3 C18 N4 175.7(4) . . . . ? O2 C18 N4 C19 2.2(7) . . . . ? N3 C18 N4 C19 -179.3(5) . . . . ? 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 O1 0.86 2.19 2.975(5) 151 1_655 N2 H2A O1 0.86 2.11 2.916(5) 155 1_655 N3 H3A O2 0.86 2.2 2.978(5) 150 1_455 N4 H4A O2 0.86 2.12 2.918(5) 154.5 1_455