# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Gary Nichol' _publ_contact_author_email GSNICHOL@EMAIL.ARIZONA.EDU _publ_section_title ; Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl) (phenyl)amino)alcanoic acids ; loop_ _publ_author_name 'Gary Nichol' 'Victor Hruby' 'Ruben Vardanyan' data_1 _database_code_depnum_ccdc_archive 'CCDC 753887' #TrackingRef 'combined_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N2 O3' _chemical_formula_sum 'C23 H28 N2 O3' _chemical_formula_weight 380.47 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 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 19.1839(8) _cell_length_b 9.7221(4) _cell_length_c 22.3927(10) _cell_angle_alpha 90 _cell_angle_beta 99.843(10) _cell_angle_gamma 90 _cell_volume 4114.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4896 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 31.08 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details 'TWINABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source beamline 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 77585 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 31.13 _reflns_number_total 5087 _reflns_number_gt 4399 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0552P)^2^+2.1228P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5087 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 O1 O 0.19409(4) 0.91476(10) 0.28981(4) 0.0310(2) Uani 1 1 d . . . O2 O 0.02575(4) 0.81239(8) 0.31563(4) 0.02342(17) Uani 1 1 d . . . H2O H -0.0176(11) 0.859(2) 0.2741(9) 0.074(6) Uiso 1 1 d . . . O3 O 0.05534(4) 1.02971(8) 0.34149(4) 0.02581(18) Uani 1 1 d . . . N1 N 0.28310(4) 1.04377(9) 0.34159(4) 0.01935(18) Uani 1 1 d . . . N2 N 0.43504(4) 1.11223(9) 0.22463(4) 0.01890(18) Uani 1 1 d . . . C1 C 0.22343(5) 0.96473(11) 0.33795(5) 0.0210(2) Uani 1 1 d . . . C2 C 0.19430(5) 0.94391(12) 0.39626(5) 0.0226(2) Uani 1 1 d . . . H2A H 0.1799 1.0339 0.4110 0.027 Uiso 1 1 calc R . . H2B H 0.2318 0.9052 0.4277 0.027 Uiso 1 1 calc R . . C3 C 0.13078(5) 0.84704(11) 0.38648(5) 0.0215(2) Uani 1 1 d . . . H3A H 0.1446 0.7598 0.3690 0.026 Uiso 1 1 calc R . . H3B H 0.1175 0.8256 0.4263 0.026 Uiso 1 1 calc R . . C4 C 0.06678(5) 0.90585(11) 0.34498(4) 0.0192(2) Uani 1 1 d . . . C5 C 0.32244(5) 1.08582(12) 0.39918(5) 0.0227(2) Uani 1 1 d . . . C6 C 0.37168(6) 0.99567(14) 0.43160(5) 0.0291(3) Uani 1 1 d . . . H6 H 0.3796 0.9078 0.4154 0.035 Uiso 1 1 calc R . . C7 C 0.40895(7) 1.03529(17) 0.48757(6) 0.0404(3) Uani 1 1 d . . . H7 H 0.4421 0.9739 0.5100 0.048 Uiso 1 1 calc R . . C8 C 0.39815(9) 1.16327(18) 0.51077(6) 0.0482(4) Uani 1 1 d . . . H8 H 0.4239 1.1898 0.5491 0.058 Uiso 1 1 calc R . . C9 C 0.34999(10) 1.25353(16) 0.47852(6) 0.0478(4) Uani 1 1 d . . . H9 H 0.3429 1.3418 0.4947 0.057 Uiso 1 1 calc R . . C10 C 0.31180(7) 1.21458(13) 0.42219(5) 0.0334(3) Uani 1 1 d . . . H10 H 0.2788 1.2762 0.3999 0.040 Uiso 1 1 calc R . . C11 C 0.31548(5) 1.06077(11) 0.28675(5) 0.0190(2) Uani 1 1 d . . . H11 H 0.2771 1.0496 0.2508 0.023 Uiso 1 1 calc R . . C12 C 0.37153(6) 0.95122(11) 0.28219(5) 0.0227(2) Uani 1 1 d . . . H12A H 0.4090 0.9559 0.3185 0.027 Uiso 1 1 calc R . . H12B H 0.3496 0.8588 0.2810 0.027 Uiso 1 1 calc R . . C13 C 0.40418(6) 0.97248(11) 0.22547(5) 0.0230(2) Uani 1 1 d . . . H13A H 0.4416 0.9029 0.2243 0.028 Uiso 1 1 calc R . . H13B H 0.3674 0.9598 0.1891 0.028 Uiso 1 1 calc R . . C14 C 0.37908(5) 1.21776(11) 0.22538(5) 0.0209(2) Uani 1 1 d . . . H14A H 0.3416 1.2058 0.1895 0.025 Uiso 1 1 calc R . . H14B H 0.3996 1.3107 0.2235 0.025 Uiso 1 1 calc R . . C15 C 0.34710(5) 1.20415(11) 0.28307(5) 0.0203(2) Uani 1 1 d . . . H15A H 0.3098 1.2744 0.2831 0.024 Uiso 1 1 calc R . . H15B H 0.3842 1.2201 0.3189 0.024 Uiso 1 1 calc R . . C16 C 0.47082(5) 1.13381(11) 0.17146(5) 0.0216(2) Uani 1 1 d . . . H16A H 0.4852 1.2314 0.1702 0.026 Uiso 1 1 calc R . . H16B H 0.4369 1.1143 0.1339 0.026 Uiso 1 1 calc R . . C17 C 0.53620(6) 1.04228(12) 0.17317(5) 0.0240(2) Uani 1 1 d . . . H17A H 0.5666 1.0507 0.2134 0.029 Uiso 1 1 calc R . . H17B H 0.5209 0.9451 0.1678 0.029 Uiso 1 1 calc R . . C18 C 0.57904(5) 1.07985(11) 0.12446(5) 0.0202(2) Uani 1 1 d . . . C19 C 0.54722(6) 1.09835(11) 0.06408(5) 0.0226(2) Uani 1 1 d . . . H19 H 0.4974 1.0893 0.0532 0.027 Uiso 1 1 calc R . . C20 C 0.58709(6) 1.12967(12) 0.01953(5) 0.0248(2) Uani 1 1 d . . . H20 H 0.5643 1.1432 -0.0212 0.030 Uiso 1 1 calc R . . C21 C 0.66017(6) 1.14118(13) 0.03450(5) 0.0275(2) Uani 1 1 d . . . H21 H 0.6877 1.1612 0.0041 0.033 Uiso 1 1 calc R . . C22 C 0.69270(6) 1.12306(13) 0.09440(5) 0.0282(2) Uani 1 1 d . . . H22 H 0.7427 1.1305 0.1049 0.034 Uiso 1 1 calc R . . C23 C 0.65258(6) 1.09402(11) 0.13921(5) 0.0236(2) Uani 1 1 d . . . H23 H 0.6753 1.0837 0.1801 0.028 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 0.0244(4) 0.0479(5) 0.0213(4) -0.0067(3) 0.0053(3) -0.0133(4) O2 0.0194(3) 0.0202(4) 0.0296(4) -0.0015(3) 0.0014(3) -0.0015(3) O3 0.0269(4) 0.0195(4) 0.0301(4) 0.0014(3) 0.0023(3) -0.0005(3) N1 0.0161(4) 0.0238(4) 0.0182(4) 0.0002(3) 0.0033(3) -0.0022(3) N2 0.0173(4) 0.0186(4) 0.0219(4) 0.0024(3) 0.0062(3) 0.0011(3) C1 0.0159(4) 0.0258(5) 0.0216(5) 0.0000(4) 0.0038(4) -0.0008(4) C2 0.0188(5) 0.0296(5) 0.0197(5) -0.0006(4) 0.0045(4) -0.0036(4) C3 0.0186(4) 0.0230(5) 0.0233(5) 0.0023(4) 0.0046(4) -0.0012(4) C4 0.0186(4) 0.0211(5) 0.0196(5) 0.0016(4) 0.0081(4) -0.0013(4) C5 0.0203(5) 0.0280(5) 0.0196(5) 0.0027(4) 0.0028(4) -0.0077(4) C6 0.0217(5) 0.0394(7) 0.0261(6) 0.0086(5) 0.0037(4) -0.0040(5) C7 0.0274(6) 0.0625(9) 0.0286(6) 0.0162(6) -0.0029(5) -0.0148(6) C8 0.0533(8) 0.0637(10) 0.0238(6) 0.0042(6) -0.0043(6) -0.0358(8) C9 0.0733(10) 0.0380(8) 0.0315(7) -0.0070(6) 0.0077(7) -0.0258(7) C10 0.0454(7) 0.0279(6) 0.0264(6) -0.0001(5) 0.0050(5) -0.0071(5) C11 0.0157(4) 0.0225(5) 0.0192(5) 0.0017(4) 0.0043(4) -0.0003(4) C12 0.0229(5) 0.0190(5) 0.0282(5) 0.0032(4) 0.0101(4) 0.0012(4) C13 0.0245(5) 0.0183(5) 0.0279(5) -0.0005(4) 0.0099(4) -0.0005(4) C14 0.0195(5) 0.0198(5) 0.0242(5) 0.0040(4) 0.0056(4) 0.0032(4) C15 0.0187(4) 0.0191(5) 0.0240(5) 0.0021(4) 0.0063(4) 0.0022(4) C16 0.0221(5) 0.0223(5) 0.0218(5) 0.0041(4) 0.0079(4) 0.0026(4) C17 0.0234(5) 0.0260(5) 0.0243(5) 0.0049(4) 0.0092(4) 0.0051(4) C18 0.0216(5) 0.0189(5) 0.0215(5) 0.0006(4) 0.0073(4) 0.0019(4) C19 0.0200(5) 0.0252(5) 0.0229(5) 0.0007(4) 0.0045(4) -0.0015(4) C20 0.0266(5) 0.0273(5) 0.0207(5) 0.0011(4) 0.0045(4) -0.0026(4) C21 0.0260(5) 0.0317(6) 0.0269(5) 0.0037(4) 0.0108(4) -0.0024(4) C22 0.0192(5) 0.0342(6) 0.0316(6) 0.0040(5) 0.0052(4) -0.0015(4) C23 0.0224(5) 0.0249(5) 0.0233(5) 0.0018(4) 0.0031(4) 0.0012(4) _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 1.2278(13) . ? O2 H2O 1.22(2) . ? O2 C4 1.3040(13) . ? O3 C4 1.2241(13) . ? N1 C1 1.3695(13) . ? N1 C5 1.4378(13) . ? N1 C11 1.4772(12) . ? N2 C13 1.4834(13) . ? N2 C14 1.4872(13) . ? N2 C16 1.4873(13) . ? C1 C2 1.5191(14) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C2 C3 1.5260(14) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.5193(14) . ? C5 C6 1.3975(16) . ? C5 C10 1.3820(17) . ? C6 H6 0.950 . ? C6 C7 1.3870(18) . ? C7 H7 0.950 . ? C7 C8 1.378(2) . ? C8 H8 0.950 . ? C8 C9 1.385(2) . ? C9 H9 0.950 . ? C9 C10 1.3984(18) . ? C10 H10 0.950 . ? C11 H11 1.000 . ? C11 C12 1.5292(14) . ? C11 C15 1.5281(14) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C12 C13 1.5233(14) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C14 C15 1.5276(14) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C16 C17 1.5329(14) . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C17 C18 1.5181(14) . ? C18 C19 1.3967(15) . ? C18 C23 1.3998(15) . ? C19 H19 0.950 . ? C19 C20 1.3906(15) . ? C20 H20 0.950 . ? C20 C21 1.3893(16) . ? C21 H21 0.950 . ? C21 C22 1.3905(16) . ? C22 H22 0.950 . ? C22 C23 1.3938(15) . ? C23 H23 0.950 . ? 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 H2O O2 C4 113.3(10) . . ? C1 N1 C5 121.21(8) . . ? C1 N1 C11 118.64(8) . . ? C5 N1 C11 118.89(8) . . ? C13 N2 C14 109.95(8) . . ? C13 N2 C16 112.28(8) . . ? C14 N2 C16 110.15(8) . . ? O1 C1 N1 121.83(10) . . ? O1 C1 C2 121.40(9) . . ? N1 C1 C2 116.76(9) . . ? C1 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C1 C2 C3 111.17(9) . . ? H2A C2 H2B 108.0 . . ? H2A C2 C3 109.4 . . ? H2B C2 C3 109.4 . . ? C2 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C2 C3 C4 113.42(9) . . ? H3A C3 H3B 107.7 . . ? H3A C3 C4 108.9 . . ? H3B C3 C4 108.9 . . ? O2 C4 O3 124.55(10) . . ? O2 C4 C3 113.65(9) . . ? O3 C4 C3 121.78(9) . . ? N1 C5 C6 119.49(11) . . ? N1 C5 C10 120.23(10) . . ? C6 C5 C10 120.28(11) . . ? C5 C6 H6 120.2 . . ? C5 C6 C7 119.57(13) . . ? H6 C6 C7 120.2 . . ? C6 C7 H7 119.9 . . ? C6 C7 C8 120.26(13) . . ? H7 C7 C8 119.9 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.39(12) . . ? H8 C8 C9 119.8 . . ? C8 C9 H9 120.0 . . ? C8 C9 C10 119.92(14) . . ? H9 C9 C10 120.0 . . ? C5 C10 C9 119.57(13) . . ? C5 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N1 C11 H11 107.5 . . ? N1 C11 C12 112.20(8) . . ? N1 C11 C15 111.97(8) . . ? H11 C11 C12 107.5 . . ? H11 C11 C15 107.5 . . ? C12 C11 C15 109.97(8) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 C13 110.80(9) . . ? H12A C12 H12B 108.1 . . ? H12A C12 C13 109.5 . . ? H12B C12 C13 109.5 . . ? N2 C13 C12 110.90(9) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? N2 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? N2 C14 C15 110.17(8) . . ? H14A C14 H14B 108.1 . . ? H14A C14 C15 109.6 . . ? H14B C14 C15 109.6 . . ? C11 C15 C14 110.19(8) . . ? C11 C15 H15A 109.6 . . ? C11 C15 H15B 109.6 . . ? C14 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N2 C16 H16A 109.1 . . ? N2 C16 H16B 109.1 . . ? N2 C16 C17 112.69(8) . . ? H16A C16 H16B 107.8 . . ? H16A C16 C17 109.1 . . ? H16B C16 C17 109.1 . . ? C16 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? C16 C17 C18 112.55(9) . . ? H17A C17 H17B 107.8 . . ? H17A C17 C18 109.1 . . ? H17B C17 C18 109.1 . . ? C17 C18 C19 121.72(9) . . ? C17 C18 C23 120.12(9) . . ? C19 C18 C23 118.15(10) . . ? C18 C19 H19 119.3 . . ? C18 C19 C20 121.32(10) . . ? H19 C19 C20 119.3 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 120.04(10) . . ? H20 C20 C21 120.0 . . ? C20 C21 H21 120.3 . . ? C20 C21 C22 119.38(10) . . ? H21 C21 C22 120.3 . . ? C21 C22 H22 119.7 . . ? C21 C22 C23 120.54(10) . . ? H22 C22 C23 119.7 . . ? C18 C23 C22 120.56(10) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? 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 C1 O1 -171.33(10) . . . . ? C5 N1 C1 C2 9.81(15) . . . . ? C11 N1 C1 O1 -4.33(16) . . . . ? C11 N1 C1 C2 176.81(9) . . . . ? O1 C1 C2 C3 4.65(15) . . . . ? N1 C1 C2 C3 -176.49(9) . . . . ? C1 C2 C3 C4 -66.45(12) . . . . ? C2 C3 C4 O2 151.89(9) . . . . ? C2 C3 C4 O3 -29.75(14) . . . . ? C1 N1 C5 C6 82.89(13) . . . . ? C1 N1 C5 C10 -97.33(13) . . . . ? C11 N1 C5 C6 -84.07(12) . . . . ? C11 N1 C5 C10 95.70(12) . . . . ? N1 C5 C6 C7 -179.08(10) . . . . ? C10 C5 C6 C7 1.14(17) . . . . ? C5 C6 C7 C8 -0.76(18) . . . . ? C6 C7 C8 C9 0.1(2) . . . . ? C7 C8 C9 C10 0.3(2) . . . . ? N1 C5 C10 C9 179.42(11) . . . . ? C6 C5 C10 C9 -0.81(18) . . . . ? C8 C9 C10 C5 0.1(2) . . . . ? C1 N1 C11 C12 -91.00(11) . . . . ? C1 N1 C11 C15 144.77(9) . . . . ? C5 N1 C11 C12 76.30(12) . . . . ? C5 N1 C11 C15 -47.93(12) . . . . ? N1 C11 C12 C13 -179.55(8) . . . . ? C15 C11 C12 C13 -54.22(11) . . . . ? C14 N2 C13 C12 -60.08(11) . . . . ? C16 N2 C13 C12 176.91(8) . . . . ? C11 C12 C13 N2 56.89(12) . . . . ? C13 N2 C14 C15 61.10(11) . . . . ? C16 N2 C14 C15 -174.65(8) . . . . ? N2 C14 C15 C11 -59.01(11) . . . . ? N1 C11 C15 C14 -179.27(8) . . . . ? C12 C11 C15 C14 55.27(11) . . . . ? C13 N2 C16 C17 -65.68(11) . . . . ? C14 N2 C16 C17 171.43(9) . . . . ? N2 C16 C17 C18 -171.04(9) . . . . ? C16 C17 C18 C19 -48.49(14) . . . . ? C16 C17 C18 C23 132.89(11) . . . . ? C17 C18 C19 C20 -178.51(10) . . . . ? C23 C18 C19 C20 0.14(16) . . . . ? C18 C19 C20 C21 0.95(17) . . . . ? C19 C20 C21 C22 -0.92(18) . . . . ? C20 C21 C22 C23 -0.19(19) . . . . ? C21 C22 C23 C18 1.30(18) . . . . ? C17 C18 C23 C22 177.42(11) . . . . ? C19 C18 C23 C22 -1.26(16) . . . . ? 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 O2 H2O N2 1.22(2) 1.34(2) 2.5505(12) 169.7(19) 6_575 C23 H23 O1 0.95 2.42 3.3311(14) 160.3 6_675 C13 H13A O2 0.99 2.40 3.2783(13) 147.4 7_565 C14 H14B O3 0.99 2.39 3.2398(13) 143.9 7_575 C16 H16A O3 0.99 2.45 3.3148(13) 145.8 7_575 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 31.13 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.349 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.039 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 753888' #TrackingRef 'combined_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N2 O4, H2 O, 0.5 C H4 O' _chemical_formula_sum 'C23.50 H32 N2 O5.50' _chemical_formula_weight 430.51 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2383(5) _cell_length_b 9.3034(5) _cell_length_c 14.4329(8) _cell_angle_alpha 75.858(3) _cell_angle_beta 80.777(3) _cell_angle_gamma 74.672(3) _cell_volume 1154.00(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 4.99 _cell_measurement_theta_max 67.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 0.720 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8446 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source microsource _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7213 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 68.21 _reflns_number_total 4051 _reflns_number_gt 3444 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0753P)^2^+0.4823P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4051 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.64812(14) 0.83151(14) 0.53489(8) 0.0255(3) Uani 1 1 d . . . O2 O 0.68748(14) 0.86915(14) 0.34445(8) 0.0261(3) Uani 1 1 d . . . O3 O 0.70771(15) 0.65401(14) 0.23651(9) 0.0273(3) Uani 1 1 d . . . O4 O 0.63168(18) 0.83711(16) 0.11018(10) 0.0402(4) Uani 1 1 d . . . N1 N 0.42886(16) 0.75761(16) 0.55026(10) 0.0209(3) Uani 1 1 d . . . N2 N 0.35009(16) 0.54501(16) 0.84664(10) 0.0210(3) Uani 1 1 d . . . H2N H 0.320(3) 0.470(3) 0.8208(17) 0.040(6) Uiso 1 1 d . . . C1 C 0.54715(19) 0.81156(18) 0.49742(12) 0.0214(4) Uani 1 1 d . . . C2 C 0.54552(19) 0.84476(19) 0.38889(12) 0.0231(4) Uani 1 1 d . . . H2A H 0.5248 0.7576 0.3696 0.028 Uiso 1 1 calc R . . H2B H 0.4650 0.9365 0.3684 0.028 Uiso 1 1 calc R . . C3 C 0.6857(2) 0.9134(2) 0.24339(12) 0.0282(4) Uani 1 1 d . . . H3A H 0.7793 0.9473 0.2155 0.034 Uiso 1 1 calc R . . H3B H 0.5998 1.0023 0.2288 0.034 Uiso 1 1 calc R . . C4 C 0.6730(2) 0.7907(2) 0.19287(12) 0.0254(4) Uani 1 1 d . . . C5 C 0.30595(19) 0.74230(19) 0.50593(11) 0.0213(4) Uani 1 1 d . . . C6 C 0.2876(2) 0.5981(2) 0.50649(12) 0.0243(4) Uani 1 1 d . . . H6 H 0.3586 0.5095 0.5336 0.029 Uiso 1 1 calc R . . C7 C 0.1652(2) 0.5841(2) 0.46728(13) 0.0271(4) Uani 1 1 d . . . H7 H 0.1523 0.4858 0.4681 0.033 Uiso 1 1 calc R . . C8 C 0.0616(2) 0.7138(2) 0.42673(13) 0.0286(4) Uani 1 1 d . . . H8 H -0.0218 0.7043 0.3997 0.034 Uiso 1 1 calc R . . C9 C 0.0809(2) 0.8574(2) 0.42601(13) 0.0294(4) Uani 1 1 d . . . H9 H 0.0109 0.9461 0.3978 0.035 Uiso 1 1 calc R . . C10 C 0.2020(2) 0.8719(2) 0.46625(12) 0.0249(4) Uani 1 1 d . . . H10 H 0.2136 0.9702 0.4666 0.030 Uiso 1 1 calc R . . C11 C 0.42182(19) 0.72878(19) 0.65651(11) 0.0214(4) Uani 1 1 d . . . H11 H 0.4584 0.8105 0.6732 0.026 Uiso 1 1 calc R . . C12 C 0.25989(19) 0.73769(19) 0.70275(12) 0.0231(4) Uani 1 1 d . . . H12A H 0.1980 0.8419 0.6814 0.028 Uiso 1 1 calc R . . H12B H 0.2172 0.6659 0.6811 0.028 Uiso 1 1 calc R . . C13 C 0.2517(2) 0.69902(19) 0.81200(12) 0.0233(4) Uani 1 1 d . . . H13A H 0.2845 0.7768 0.8343 0.028 Uiso 1 1 calc R . . H13B H 0.1461 0.7006 0.8394 0.028 Uiso 1 1 calc R . . C14 C 0.51060(19) 0.5428(2) 0.80693(12) 0.0255(4) Uani 1 1 d . . . H14A H 0.5761 0.4418 0.8315 0.031 Uiso 1 1 calc R . . H14B H 0.5446 0.6209 0.8282 0.031 Uiso 1 1 calc R . . C15 C 0.52400(19) 0.5753(2) 0.69740(12) 0.0238(4) Uani 1 1 d . . . H15A H 0.4962 0.4933 0.6765 0.029 Uiso 1 1 calc R . . H15B H 0.6300 0.5755 0.6718 0.029 Uiso 1 1 calc R . . C16 C 0.33560(19) 0.4974(2) 0.95423(12) 0.0234(4) Uani 1 1 d . . . H16A H 0.3523 0.5784 0.9820 0.028 Uiso 1 1 calc R . . H16B H 0.4137 0.4033 0.9742 0.028 Uiso 1 1 calc R . . C17 C 0.1800(2) 0.4687(2) 0.99241(12) 0.0270(4) Uani 1 1 d . . . H17A H 0.1038 0.5669 0.9814 0.032 Uiso 1 1 calc R . . H17B H 0.1567 0.4016 0.9560 0.032 Uiso 1 1 calc R . . C18 C 0.16788(19) 0.3957(2) 1.09816(12) 0.0259(4) Uani 1 1 d . . . C19 C 0.2201(2) 0.2393(2) 1.12975(14) 0.0335(4) Uani 1 1 d . . . H19 H 0.2670 0.1778 1.0845 0.040 Uiso 1 1 calc R . . C20 C 0.2044(2) 0.1719(3) 1.22710(15) 0.0396(5) Uani 1 1 d . . . H20 H 0.2413 0.0651 1.2478 0.048 Uiso 1 1 calc R . . C21 C 0.1355(2) 0.2597(3) 1.29375(14) 0.0370(5) Uani 1 1 d . . . H21 H 0.1248 0.2136 1.3601 0.044 Uiso 1 1 calc R . . C22 C 0.0820(2) 0.4156(3) 1.26299(14) 0.0340(4) Uani 1 1 d . . . H22 H 0.0334 0.4764 1.3084 0.041 Uiso 1 1 calc R . . C23 C 0.0990(2) 0.4835(2) 1.16606(13) 0.0291(4) Uani 1 1 d . . . H23 H 0.0634 0.5906 1.1458 0.035 Uiso 1 1 calc R . . O5 O 0.6006(2) 1.1411(2) 0.00546(15) 0.0593(5) Uani 1 1 d . . . H5A H 0.617(4) 1.038(5) 0.040(3) 0.097(12) Uiso 1 1 d . . . H5B H 0.548(5) 1.154(5) -0.046(3) 0.120(16) Uiso 1 1 d . . . O6 O 0.8806(6) 1.1772(5) -0.0181(3) 0.0863(15) Uani 0.50 1 d P A -1 H6A H 0.8011 1.1455 -0.0069 0.104 Uiso 0.50 1 calc PR A -1 C24 C 0.9888(5) 1.0742(5) -0.0385(4) 0.0410(11) Uani 0.50 1 d P A -1 H24A H 1.0827 1.1076 -0.0455 0.061 Uiso 0.50 1 calc PR A -1 H24B H 0.9762 1.0509 -0.0989 0.061 Uiso 0.50 1 calc PR A -1 H24C H 0.9928 0.9826 0.0130 0.061 Uiso 0.50 1 calc PR A -1 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 0.0256(6) 0.0289(6) 0.0233(6) -0.0035(5) -0.0011(5) -0.0117(5) O2 0.0299(7) 0.0310(7) 0.0200(6) -0.0059(5) 0.0046(5) -0.0151(5) O3 0.0355(7) 0.0232(6) 0.0230(6) -0.0042(5) 0.0000(5) -0.0090(5) O4 0.0592(10) 0.0328(8) 0.0264(7) -0.0044(6) -0.0120(6) -0.0042(7) N1 0.0236(7) 0.0217(7) 0.0179(7) -0.0032(5) 0.0001(5) -0.0083(6) N2 0.0210(7) 0.0234(7) 0.0177(7) -0.0023(6) 0.0003(5) -0.0066(6) C1 0.0245(8) 0.0172(8) 0.0215(8) -0.0037(6) 0.0003(6) -0.0049(6) C2 0.0242(9) 0.0230(8) 0.0225(9) -0.0044(7) 0.0015(7) -0.0087(7) C3 0.0384(10) 0.0243(9) 0.0212(9) -0.0026(7) 0.0062(7) -0.0139(8) C4 0.0272(9) 0.0253(9) 0.0221(9) -0.0038(7) 0.0029(7) -0.0076(7) C5 0.0218(8) 0.0259(9) 0.0162(8) -0.0050(6) 0.0026(6) -0.0079(7) C6 0.0249(9) 0.0237(8) 0.0231(8) -0.0050(7) 0.0013(7) -0.0060(7) C7 0.0280(9) 0.0286(9) 0.0276(9) -0.0083(7) 0.0030(7) -0.0127(7) C8 0.0246(9) 0.0387(10) 0.0249(9) -0.0083(8) -0.0010(7) -0.0111(8) C9 0.0276(9) 0.0309(9) 0.0268(9) -0.0018(7) -0.0036(7) -0.0053(7) C10 0.0278(9) 0.0232(8) 0.0222(8) -0.0032(7) 0.0006(7) -0.0071(7) C11 0.0256(9) 0.0210(8) 0.0178(8) -0.0034(6) 0.0003(6) -0.0084(7) C12 0.0230(9) 0.0239(8) 0.0203(8) -0.0030(6) 0.0002(6) -0.0046(7) C13 0.0260(9) 0.0220(8) 0.0198(8) -0.0037(6) 0.0013(6) -0.0047(7) C14 0.0209(9) 0.0310(9) 0.0225(9) -0.0006(7) -0.0001(7) -0.0084(7) C15 0.0214(8) 0.0253(9) 0.0215(9) -0.0017(7) 0.0019(6) -0.0057(7) C16 0.0249(9) 0.0284(9) 0.0166(8) -0.0009(7) -0.0015(6) -0.0095(7) C17 0.0249(9) 0.0366(10) 0.0192(9) -0.0007(7) -0.0006(7) -0.0123(7) C18 0.0218(8) 0.0358(10) 0.0205(9) -0.0003(7) -0.0022(6) -0.0126(7) C19 0.0295(10) 0.0373(11) 0.0292(10) -0.0019(8) 0.0011(7) -0.0072(8) C20 0.0344(11) 0.0400(11) 0.0351(11) 0.0085(9) -0.0034(8) -0.0080(9) C21 0.0335(10) 0.0545(13) 0.0202(9) 0.0073(8) -0.0052(8) -0.0182(9) C22 0.0337(10) 0.0504(12) 0.0224(9) -0.0070(8) -0.0024(7) -0.0186(9) C23 0.0288(9) 0.0355(10) 0.0253(9) -0.0035(8) -0.0032(7) -0.0139(8) O5 0.0631(12) 0.0477(10) 0.0576(11) 0.0055(9) -0.0166(9) -0.0061(9) O6 0.118(4) 0.063(3) 0.086(3) -0.017(2) 0.005(3) -0.042(3) C24 0.026(2) 0.029(2) 0.056(3) 0.001(2) 0.0210(18) -0.0106(16) _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 1.224(2) . ? O2 C2 1.414(2) . ? O2 C3 1.417(2) . ? O3 C4 1.255(2) . ? O4 C4 1.251(2) . ? N1 C1 1.365(2) . ? N1 C5 1.443(2) . ? N1 C11 1.485(2) . ? N2 H2N 0.98(3) . ? N2 C13 1.495(2) . ? N2 C14 1.498(2) . ? N2 C16 1.501(2) . ? C1 C2 1.523(2) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.533(2) . ? C5 C6 1.394(2) . ? C5 C10 1.390(2) . ? C6 H6 0.950 . ? C6 C7 1.391(3) . ? C7 H7 0.950 . ? C7 C8 1.393(3) . ? C8 H8 0.950 . ? C8 C9 1.391(3) . ? C9 H9 0.950 . ? C9 C10 1.390(3) . ? C10 H10 0.950 . ? C11 H11 1.000 . ? C11 C12 1.527(2) . ? C11 C15 1.527(2) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C12 C13 1.523(2) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C14 C15 1.526(2) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C16 C17 1.523(2) . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C17 C18 1.511(2) . ? C18 C19 1.390(3) . ? C18 C23 1.396(3) . ? C19 H19 0.950 . ? C19 C20 1.393(3) . ? C20 H20 0.950 . ? C20 C21 1.382(3) . ? C21 H21 0.950 . ? C21 C22 1.386(3) . ? C22 H22 0.950 . ? C22 C23 1.390(3) . ? C23 H23 0.950 . ? O5 H5A 0.95(4) . ? O5 H5B 0.91(5) . ? O6 H6A 0.840 . ? O6 C24 1.241(6) . ? C24 H24A 0.980 . ? C24 H24B 0.980 . ? C24 H24C 0.980 . ? 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 O2 C3 110.40(13) . . ? C1 N1 C5 121.93(14) . . ? C1 N1 C11 117.85(14) . . ? C5 N1 C11 119.96(13) . . ? H2N N2 C13 108.6(14) . . ? H2N N2 C14 106.6(14) . . ? H2N N2 C16 108.2(14) . . ? C13 N2 C14 109.75(13) . . ? C13 N2 C16 112.27(13) . . ? C14 N2 C16 111.28(13) . . ? O1 C1 N1 122.17(15) . . ? O1 C1 C2 122.22(15) . . ? N1 C1 C2 115.61(14) . . ? O2 C2 C1 108.93(14) . . ? O2 C2 H2A 109.9 . . ? O2 C2 H2B 109.9 . . ? C1 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O2 C3 H3A 108.3 . . ? O2 C3 H3B 108.3 . . ? O2 C3 C4 115.95(14) . . ? H3A C3 H3B 107.4 . . ? H3A C3 C4 108.3 . . ? H3B C3 C4 108.3 . . ? O3 C4 O4 125.91(17) . . ? O3 C4 C3 117.86(15) . . ? O4 C4 C3 116.21(16) . . ? N1 C5 C6 120.24(15) . . ? N1 C5 C10 119.72(15) . . ? C6 C5 C10 119.98(16) . . ? C5 C6 H6 120.0 . . ? C5 C6 C7 119.94(16) . . ? H6 C6 C7 120.0 . . ? C6 C7 H7 119.9 . . ? C6 C7 C8 120.18(16) . . ? H7 C7 C8 119.9 . . ? C7 C8 H8 120.2 . . ? C7 C8 C9 119.59(17) . . ? H8 C8 C9 120.2 . . ? C8 C9 H9 119.8 . . ? C8 C9 C10 120.40(17) . . ? H9 C9 C10 119.8 . . ? C5 C10 C9 119.89(16) . . ? C5 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N1 C11 H11 107.8 . . ? N1 C11 C12 111.09(13) . . ? N1 C11 C15 111.65(13) . . ? H11 C11 C12 107.8 . . ? H11 C11 C15 107.8 . . ? C12 C11 C15 110.40(13) . . ? C11 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C11 C12 C13 111.80(14) . . ? H12A C12 H12B 107.9 . . ? H12A C12 C13 109.3 . . ? H12B C12 C13 109.3 . . ? N2 C13 C12 110.69(13) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N2 C14 H14A 109.7 . . ? N2 C14 H14B 109.7 . . ? N2 C14 C15 109.93(14) . . ? H14A C14 H14B 108.2 . . ? H14A C14 C15 109.7 . . ? H14B C14 C15 109.7 . . ? C11 C15 C14 111.42(14) . . ? C11 C15 H15A 109.3 . . ? C11 C15 H15B 109.3 . . ? C14 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? N2 C16 C17 110.84(13) . . ? H16A C16 H16B 108.1 . . ? H16A C16 C17 109.5 . . ? H16B C16 C17 109.5 . . ? C16 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? C16 C17 C18 112.94(14) . . ? H17A C17 H17B 107.8 . . ? H17A C17 C18 109.0 . . ? H17B C17 C18 109.0 . . ? C17 C18 C19 120.88(17) . . ? C17 C18 C23 120.54(17) . . ? C19 C18 C23 118.55(16) . . ? C18 C19 H19 119.7 . . ? C18 C19 C20 120.65(19) . . ? H19 C19 C20 119.7 . . ? C19 C20 H20 119.8 . . ? C19 C20 C21 120.4(2) . . ? H20 C20 C21 119.8 . . ? C20 C21 H21 120.3 . . ? C20 C21 C22 119.48(17) . . ? H21 C21 C22 120.3 . . ? C21 C22 H22 119.8 . . ? C21 C22 C23 120.31(19) . . ? H22 C22 C23 119.8 . . ? C18 C23 C22 120.64(18) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? H5A O5 H5B 111(4) . . ? H6A O6 C24 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 C1 O1 176.50(15) . . . . ? C5 N1 C1 C2 -3.7(2) . . . . ? C11 N1 C1 O1 2.4(2) . . . . ? C11 N1 C1 C2 -177.77(13) . . . . ? C3 O2 C2 C1 -174.95(13) . . . . ? O1 C1 C2 O2 11.6(2) . . . . ? N1 C1 C2 O2 -168.17(14) . . . . ? C2 O2 C3 C4 -68.14(19) . . . . ? O2 C3 C4 O3 -19.8(2) . . . . ? O2 C3 C4 O4 161.73(16) . . . . ? C1 N1 C5 C6 110.78(18) . . . . ? C1 N1 C5 C10 -72.0(2) . . . . ? C11 N1 C5 C6 -75.3(2) . . . . ? C11 N1 C5 C10 101.97(18) . . . . ? N1 C5 C6 C7 177.26(15) . . . . ? C10 C5 C6 C7 0.0(2) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? N1 C5 C10 C9 -178.11(15) . . . . ? C6 C5 C10 C9 -0.9(3) . . . . ? C8 C9 C10 C5 1.2(3) . . . . ? C1 N1 C11 C12 155.14(14) . . . . ? C1 N1 C11 C15 -81.15(18) . . . . ? C5 N1 C11 C12 -19.1(2) . . . . ? C5 N1 C11 C15 104.65(17) . . . . ? N1 C11 C12 C13 176.58(13) . . . . ? C15 C11 C12 C13 52.16(18) . . . . ? C14 N2 C13 C12 60.23(18) . . . . ? C16 N2 C13 C12 -175.44(13) . . . . ? C11 C12 C13 N2 -56.17(18) . . . . ? C13 N2 C14 C15 -61.03(18) . . . . ? C16 N2 C14 C15 174.07(14) . . . . ? N2 C14 C15 C11 58.00(19) . . . . ? N1 C11 C15 C14 -177.27(13) . . . . ? C12 C11 C15 C14 -53.17(18) . . . . ? C13 N2 C16 C17 68.06(18) . . . . ? C14 N2 C16 C17 -168.46(14) . . . . ? N2 C16 C17 C18 170.46(15) . . . . ? C16 C17 C18 C19 -81.5(2) . . . . ? C16 C17 C18 C23 100.7(2) . . . . ? C17 C18 C19 C20 -177.97(18) . . . . ? C23 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? C20 C21 C22 C23 -0.7(3) . . . . ? C21 C22 C23 C18 1.0(3) . . . . ? C17 C18 C23 C22 177.23(16) . . . . ? C19 C18 C23 C22 -0.5(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 N2 H2N O3 0.98(3) 1.66(3) 2.6396(19) 171(2) 2_666 O5 H5A O4 0.95(4) 1.88(4) 2.826(2) 175(4) . O5 H5B O4 0.91(5) 2.01(5) 2.861(3) 155(4) 2_675 O6 H6A O5 0.84 1.84 2.654(6) 161.8 . C10 H10 O1 0.95 2.50 3.395(2) 156.8 2_676 C23 H23 O6 0.95 2.58 3.384(5) 142.3 2_676 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 68.21 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.674 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 753889' #TrackingRef 'combined_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 N2 O3, C4 H8 O2' _chemical_formula_sum 'C28 H38 N2 O5' _chemical_formula_weight 482.60 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3005(4) _cell_length_b 9.7222(5) _cell_length_c 14.4230(7) _cell_angle_alpha 78.622(4) _cell_angle_beta 75.813(3) _cell_angle_gamma 74.623(3) _cell_volume 1206.84(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2685 _cell_measurement_theta_min 4.77 _cell_measurement_theta_max 67.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.731 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8150 _exptl_absorpt_correction_T_max 0.9123 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube with Miracol optics' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4181 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 67.45 _reflns_number_total 4181 _reflns_number_gt 3304 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0681P)^2^+0.3906P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4181 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.67154(14) 0.36814(13) 0.45780(9) 0.0269(3) Uani 1 1 d . . . O2 O 0.66467(19) 0.3908(3) 0.88685(16) 0.0814(8) Uani 1 1 d . . . O3 O 0.84889(14) 0.28153(15) 0.77997(10) 0.0310(3) Uani 1 1 d . . . N1 N 0.74523(16) 0.57672(16) 0.44228(10) 0.0223(3) Uani 1 1 d . . . N2 N 0.95671(16) 0.65783(16) 0.14306(11) 0.0234(3) Uani 1 1 d . . . H2N H 1.040(2) 0.697(2) 0.1707(14) 0.028 Uiso 1 1 d . . . C1 C 0.69245(18) 0.46101(19) 0.49670(13) 0.0222(4) Uani 1 1 d . . . C2 C 0.6605(2) 0.4521(2) 0.60560(13) 0.0245(4) Uani 1 1 d . . . H2A H 0.5649 0.5226 0.6266 0.029 Uiso 1 1 calc R . . H2B H 0.7439 0.4789 0.6244 0.029 Uiso 1 1 calc R . . C3 C 0.6462(2) 0.3028(2) 0.65769(13) 0.0263(4) Uani 1 1 d . . . H3A H 0.7458 0.2341 0.6433 0.032 Uiso 1 1 calc R . . H3B H 0.5716 0.2708 0.6332 0.032 Uiso 1 1 calc R . . C4 C 0.5952(2) 0.3000(2) 0.76693(14) 0.0313(4) Uani 1 1 d . . . H4A H 0.4986 0.3730 0.7807 0.038 Uiso 1 1 calc R . . H4B H 0.5744 0.2044 0.7962 0.038 Uiso 1 1 calc R . . C5 C 0.7108(2) 0.3293(2) 0.81484(14) 0.0320(4) Uani 1 1 d . . . C6 C 0.76157(19) 0.69056(19) 0.48692(12) 0.0224(4) Uani 1 1 d . . . C7 C 0.6332(2) 0.7868(2) 0.52728(13) 0.0258(4) Uani 1 1 d . . . H7 H 0.5346 0.7782 0.5253 0.031 Uiso 1 1 calc R . . C8 C 0.6493(2) 0.8960(2) 0.57056(14) 0.0313(4) Uani 1 1 d . . . H8 H 0.5615 0.9610 0.5994 0.038 Uiso 1 1 calc R . . C9 C 0.7931(2) 0.9105(2) 0.57178(14) 0.0317(4) Uani 1 1 d . . . H9 H 0.8036 0.9855 0.6013 0.038 Uiso 1 1 calc R . . C10 C 0.9214(2) 0.8159(2) 0.53009(14) 0.0302(4) Uani 1 1 d . . . H10 H 1.0199 0.8267 0.5303 0.036 Uiso 1 1 calc R . . C11 C 0.9061(2) 0.7051(2) 0.48792(13) 0.0268(4) Uani 1 1 d . . . H11 H 0.9941 0.6394 0.4599 0.032 Uiso 1 1 calc R . . C12 C 0.77406(19) 0.58807(19) 0.33557(13) 0.0235(4) Uani 1 1 d . . . H12 H 0.6902 0.5574 0.3188 0.028 Uiso 1 1 calc R . . C13 C 0.7712(2) 0.7424(2) 0.28721(13) 0.0247(4) Uani 1 1 d . . . H13A H 0.8474 0.7783 0.3073 0.030 Uiso 1 1 calc R . . H13B H 0.6696 0.8041 0.3089 0.030 Uiso 1 1 calc R . . C14 C 0.80563(19) 0.7535(2) 0.17765(13) 0.0257(4) Uani 1 1 d . . . H14A H 0.7250 0.7253 0.1569 0.031 Uiso 1 1 calc R . . H14B H 0.8064 0.8546 0.1486 0.031 Uiso 1 1 calc R . . C15 C 0.9555(2) 0.5047(2) 0.18595(14) 0.0291(4) Uani 1 1 d . . . H15A H 1.0551 0.4415 0.1621 0.035 Uiso 1 1 calc R . . H15B H 0.8759 0.4745 0.1653 0.035 Uiso 1 1 calc R . . C16 C 0.9243(2) 0.4881(2) 0.29580(13) 0.0261(4) Uani 1 1 d . . . H16A H 1.0085 0.5104 0.3164 0.031 Uiso 1 1 calc R . . H16B H 0.9203 0.3870 0.3227 0.031 Uiso 1 1 calc R . . C17 C 0.9998(2) 0.6743(2) 0.03510(13) 0.0283(4) Uani 1 1 d . . . H17A H 0.9150 0.6636 0.0089 0.034 Uiso 1 1 calc R . . H17B H 1.0902 0.5975 0.0151 0.034 Uiso 1 1 calc R . . C18 C 1.0353(2) 0.8205(2) -0.00605(14) 0.0314(4) Uani 1 1 d . . . H18A H 0.9412 0.8964 0.0077 0.038 Uiso 1 1 calc R . . H18B H 1.1106 0.8357 0.0267 0.038 Uiso 1 1 calc R . . C19 C 1.0979(2) 0.8355(2) -0.11410(14) 0.0300(4) Uani 1 1 d . . . C20 C 1.0144(2) 0.9289(2) -0.17758(15) 0.0348(5) Uani 1 1 d . . . H20 H 0.9152 0.9822 -0.1533 0.042 Uiso 1 1 calc R . . C21 C 1.0738(3) 0.9459(3) -0.27685(15) 0.0416(5) Uani 1 1 d . . . H21 H 1.0152 1.0112 -0.3194 0.050 Uiso 1 1 calc R . . C22 C 1.2162(3) 0.8689(3) -0.31325(16) 0.0445(6) Uani 1 1 d . . . H22 H 1.2566 0.8805 -0.3808 0.053 Uiso 1 1 calc R . . C23 C 1.2998(3) 0.7749(3) -0.25110(18) 0.0476(6) Uani 1 1 d . . . H23 H 1.3981 0.7205 -0.2762 0.057 Uiso 1 1 calc R . . C24 C 1.2423(2) 0.7580(2) -0.15142(16) 0.0376(5) Uani 1 1 d . . . H24 H 1.3020 0.6936 -0.1092 0.045 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(7) 0.0291(7) 0.0283(7) -0.0099(5) -0.0022(5) -0.0129(5) O2 0.0310(9) 0.142(2) 0.0885(15) -0.0894(15) -0.0141(9) 0.0066(10) O3 0.0206(7) 0.0416(8) 0.0337(7) -0.0091(6) -0.0051(5) -0.0095(6) N1 0.0206(7) 0.0268(8) 0.0226(8) -0.0075(6) -0.0014(6) -0.0103(6) N2 0.0216(7) 0.0257(8) 0.0239(8) -0.0076(6) 0.0015(6) -0.0099(6) C1 0.0135(8) 0.0265(9) 0.0283(9) -0.0087(7) -0.0021(7) -0.0057(7) C2 0.0210(9) 0.0283(10) 0.0271(10) -0.0095(8) -0.0025(7) -0.0088(7) C3 0.0229(9) 0.0305(10) 0.0291(10) -0.0030(8) -0.0056(7) -0.0132(8) C4 0.0242(10) 0.0430(12) 0.0289(10) -0.0027(8) -0.0036(8) -0.0151(8) C5 0.0237(10) 0.0428(12) 0.0317(10) -0.0105(9) -0.0024(8) -0.0105(8) C6 0.0229(9) 0.0246(9) 0.0219(9) -0.0061(7) -0.0036(7) -0.0076(7) C7 0.0241(9) 0.0275(10) 0.0275(10) -0.0062(8) -0.0047(7) -0.0076(7) C8 0.0344(10) 0.0279(10) 0.0315(10) -0.0094(8) -0.0048(8) -0.0048(8) C9 0.0422(11) 0.0275(10) 0.0315(10) -0.0073(8) -0.0111(9) -0.0128(9) C10 0.0298(10) 0.0321(11) 0.0347(11) -0.0029(8) -0.0114(8) -0.0141(8) C11 0.0261(9) 0.0264(10) 0.0302(10) -0.0053(8) -0.0056(8) -0.0089(7) C12 0.0208(9) 0.0291(10) 0.0241(9) -0.0077(7) -0.0023(7) -0.0109(7) C13 0.0194(8) 0.0293(10) 0.0254(10) -0.0085(8) -0.0004(7) -0.0059(7) C14 0.0198(9) 0.0306(10) 0.0279(10) -0.0083(8) -0.0008(7) -0.0085(7) C15 0.0313(10) 0.0258(10) 0.0300(10) -0.0070(8) 0.0036(8) -0.0130(8) C16 0.0261(9) 0.0254(9) 0.0262(10) -0.0065(7) 0.0016(7) -0.0092(7) C17 0.0303(10) 0.0311(10) 0.0261(10) -0.0101(8) 0.0014(8) -0.0138(8) C18 0.0397(11) 0.0324(11) 0.0270(10) -0.0093(8) -0.0009(8) -0.0181(9) C19 0.0373(11) 0.0306(10) 0.0279(10) -0.0117(8) 0.0022(8) -0.0201(9) C20 0.0400(11) 0.0376(11) 0.0327(11) -0.0106(9) -0.0055(9) -0.0166(9) C21 0.0621(15) 0.0457(13) 0.0281(11) -0.0068(9) -0.0098(10) -0.0292(11) C22 0.0704(16) 0.0437(13) 0.0269(11) -0.0107(10) 0.0028(11) -0.0332(12) C23 0.0507(14) 0.0426(13) 0.0461(14) -0.0180(11) 0.0186(11) -0.0222(11) C24 0.0397(12) 0.0345(11) 0.0374(12) -0.0052(9) 0.0028(9) -0.0163(9) _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 1.231(2) . ? O2 C5 1.229(3) . ? O3 C5 1.256(2) . ? N1 C1 1.370(2) . ? N1 C6 1.443(2) . ? N1 C12 1.483(2) . ? N2 H2N 1.13(2) . ? N2 C14 1.495(2) . ? N2 C15 1.497(2) . ? N2 C17 1.497(2) . ? C1 C2 1.515(2) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C2 C3 1.521(3) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.527(3) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C4 C5 1.523(3) . ? C6 C7 1.386(3) . ? C6 C11 1.392(2) . ? C7 H7 0.950 . ? C7 C8 1.390(3) . ? C8 H8 0.950 . ? C8 C9 1.386(3) . ? C9 H9 0.950 . ? C9 C10 1.384(3) . ? C10 H10 0.950 . ? C10 C11 1.391(3) . ? C11 H11 0.950 . ? C12 H12 1.000 . ? C12 C13 1.521(3) . ? C12 C16 1.527(3) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C13 C14 1.521(2) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C15 C16 1.523(3) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C17 C18 1.517(3) . ? C18 H18A 0.990 . ? C18 H18B 0.990 . ? C18 C19 1.516(3) . ? C19 C20 1.383(3) . ? C19 C24 1.389(3) . ? C20 H20 0.950 . ? C20 C21 1.396(3) . ? C21 H21 0.950 . ? C21 C22 1.371(4) . ? C22 H22 0.950 . ? C22 C23 1.373(4) . ? C23 H23 0.950 . ? C23 C24 1.399(3) . ? C24 H24 0.950 . ? 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 121.18(14) . . ? C1 N1 C12 118.28(13) . . ? C6 N1 C12 120.38(14) . . ? H2N N2 C14 104.4(10) . . ? H2N N2 C15 110.5(10) . . ? H2N N2 C17 108.5(10) . . ? C14 N2 C15 109.74(13) . . ? C14 N2 C17 111.96(15) . . ? C15 N2 C17 111.54(13) . . ? O1 C1 N1 120.70(16) . . ? O1 C1 C2 121.50(16) . . ? N1 C1 C2 117.80(14) . . ? C1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C1 C2 C3 112.84(14) . . ? H2A C2 H2B 107.8 . . ? H2A C2 C3 109.0 . . ? H2B C2 C3 109.0 . . ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C2 C3 C4 112.16(15) . . ? H3A C3 H3B 107.9 . . ? H3A C3 C4 109.2 . . ? H3B C3 C4 109.2 . . ? C3 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C3 C4 C5 114.01(15) . . ? H4A C4 H4B 107.6 . . ? H4A C4 C5 108.7 . . ? H4B C4 C5 108.7 . . ? O2 C5 O3 124.27(18) . . ? O2 C5 C4 118.94(18) . . ? O3 C5 C4 116.69(17) . . ? N1 C6 C7 119.86(15) . . ? N1 C6 C11 119.98(16) . . ? C7 C6 C11 120.15(16) . . ? C6 C7 H7 120.1 . . ? C6 C7 C8 119.72(16) . . ? H7 C7 C8 120.1 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.21(18) . . ? H8 C8 C9 119.9 . . ? C8 C9 H9 119.9 . . ? C8 C9 C10 120.14(17) . . ? H9 C9 C10 119.9 . . ? C9 C10 H10 120.0 . . ? C9 C10 C11 119.96(17) . . ? H10 C10 C11 120.0 . . ? C6 C11 C10 119.82(17) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N1 C12 H12 107.7 . . ? N1 C12 C13 111.63(14) . . ? N1 C12 C16 111.77(15) . . ? H12 C12 C13 107.7 . . ? H12 C12 C16 107.7 . . ? C13 C12 C16 110.25(14) . . ? C12 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? C12 C13 C14 111.72(14) . . ? H13A C13 H13B 107.9 . . ? H13A C13 C14 109.3 . . ? H13B C13 C14 109.3 . . ? N2 C14 C13 110.45(15) . . ? N2 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? C13 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? N2 C15 C16 110.68(14) . . ? H15A C15 H15B 108.1 . . ? H15A C15 C16 109.5 . . ? H15B C15 C16 109.5 . . ? C12 C16 C15 111.29(16) . . ? C12 C16 H16A 109.4 . . ? C12 C16 H16B 109.4 . . ? C15 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? N2 C17 C18 110.87(14) . . ? H17A C17 H17B 108.1 . . ? H17A C17 C18 109.5 . . ? H17B C17 C18 109.5 . . ? C17 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C17 C18 C19 112.79(15) . . ? H18A C18 H18B 107.8 . . ? H18A C18 C19 109.0 . . ? H18B C18 C19 109.0 . . ? C18 C19 C20 120.92(18) . . ? C18 C19 C24 120.62(19) . . ? C20 C19 C24 118.44(19) . . ? C19 C20 H20 119.5 . . ? C19 C20 C21 121.0(2) . . ? H20 C20 C21 119.5 . . ? C20 C21 H21 119.8 . . ? C20 C21 C22 120.3(2) . . ? H21 C21 C22 119.8 . . ? C21 C22 H22 120.3 . . ? C21 C22 C23 119.3(2) . . ? H22 C22 C23 120.3 . . ? C22 C23 H23 119.6 . . ? C22 C23 C24 120.9(2) . . ? H23 C23 C24 119.6 . . ? C19 C24 C23 120.1(2) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? 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 176.28(15) . . . . ? C6 N1 C1 C2 -3.5(2) . . . . ? C12 N1 C1 O1 0.9(2) . . . . ? C12 N1 C1 C2 -178.85(15) . . . . ? O1 C1 C2 C3 16.4(2) . . . . ? N1 C1 C2 C3 -163.85(15) . . . . ? C1 C2 C3 C4 -173.07(14) . . . . ? C2 C3 C4 C5 -66.0(2) . . . . ? C3 C4 C5 O2 148.2(2) . . . . ? C3 C4 C5 O3 -35.3(3) . . . . ? C1 N1 C6 C7 -72.2(2) . . . . ? C1 N1 C6 C11 108.9(2) . . . . ? C12 N1 C6 C7 103.01(19) . . . . ? C12 N1 C6 C11 -75.9(2) . . . . ? N1 C6 C7 C8 179.75(17) . . . . ? C11 C6 C7 C8 -1.4(3) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C6 0.7(3) . . . . ? N1 C6 C11 C10 179.30(17) . . . . ? C7 C6 C11 C10 0.4(3) . . . . ? C1 N1 C12 C13 157.79(14) . . . . ? C1 N1 C12 C16 -78.21(18) . . . . ? C6 N1 C12 C13 -17.6(2) . . . . ? C6 N1 C12 C16 106.40(17) . . . . ? N1 C12 C13 C14 178.23(13) . . . . ? C16 C12 C13 C14 53.38(18) . . . . ? C15 N2 C14 C13 59.88(18) . . . . ? C17 N2 C14 C13 -175.70(13) . . . . ? C12 C13 C14 N2 -57.26(18) . . . . ? C14 N2 C15 C16 -60.01(18) . . . . ? C17 N2 C15 C16 175.32(14) . . . . ? N2 C15 C16 C12 57.05(19) . . . . ? N1 C12 C16 C15 -177.92(13) . . . . ? C13 C12 C16 C15 -53.14(18) . . . . ? C14 N2 C17 C18 69.37(19) . . . . ? C15 N2 C17 C18 -167.22(15) . . . . ? N2 C17 C18 C19 173.07(16) . . . . ? C17 C18 C19 C20 112.0(2) . . . . ? C17 C18 C19 C24 -69.5(2) . . . . ? C18 C19 C20 C21 178.07(16) . . . . ? C24 C19 C20 C21 -0.4(3) . . . . ? C19 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C21 C22 C23 C24 -0.8(3) . . . . ? C18 C19 C24 C23 -178.81(17) . . . . ? C20 C19 C24 C23 -0.3(3) . . . . ? C22 C23 C24 C19 0.9(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 N2 H2N O3 1.13(2) 1.47(2) 2.5800(18) 167.8(18) 2_766 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 67.45 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.375 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.046 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.000 227 55 ' ' _platon_squeeze_details ; One molecule of ethyl acetate, both whole-molecule disordered and over an inversion centre, per asymmetric unit removed with SQUEEZE. ; #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 753890' #TrackingRef 'combined_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2 C24 H30 N2 O3, 2 H2 O, C H4 O' _chemical_formula_sum 'C49 H68 N4 O9' _chemical_formula_weight 857.07 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3807(4) _cell_length_b 14.8290(7) _cell_length_c 17.4244(9) _cell_angle_alpha 85.655(4) _cell_angle_beta 78.993(4) _cell_angle_gamma 76.609(3) _cell_volume 2313.31(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3927 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 67.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 0.681 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8285 _exptl_absorpt_correction_T_max 0.8826 _exptl_absorpt_process_details 'SADABS 2008/1; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source microsource _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19578 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 67.77 _reflns_number_total 8140 _reflns_number_gt 6194 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0805P)^2^+0.5370P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8140 _refine_ls_number_parameters 581 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1482 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.049 _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 0.37179(16) 0.40716(10) 0.58158(9) 0.0258(3) Uani 1 1 d . . . O2 O 0.07091(19) 0.82892(12) 0.62956(13) 0.0447(5) Uani 1 1 d . . . O3 O -0.02360(17) 0.70435(11) 0.66031(10) 0.0310(4) Uani 1 1 d . . . N1 N 0.29105(19) 0.44314(12) 0.46640(10) 0.0225(4) Uani 1 1 d . . . N2 N 0.2632(2) 0.18487(13) 0.38144(11) 0.0247(4) Uani 1 1 d . . . H2N H 0.179(3) 0.222(2) 0.3654(16) 0.038(7) Uiso 1 1 d . . . C1 C 0.3174(2) 0.46700(15) 0.53608(12) 0.0213(4) Uani 1 1 d . . . C2 C 0.2784(2) 0.56926(14) 0.55494(12) 0.0220(4) Uani 1 1 d . . . H2A H 0.1823 0.5989 0.5388 0.026 Uiso 1 1 calc R . . H2B H 0.3557 0.5996 0.5243 0.026 Uiso 1 1 calc R . . C3 C 0.2667(2) 0.58469(14) 0.64154(12) 0.0238(4) Uani 1 1 d . . . H3A H 0.3607 0.5519 0.6585 0.029 Uiso 1 1 calc R . . H3B H 0.1852 0.5577 0.6719 0.029 Uiso 1 1 calc R . . C4 C 0.2367(2) 0.68734(15) 0.65943(13) 0.0263(5) Uani 1 1 d . . . H4A H 0.2479 0.6922 0.7142 0.032 Uiso 1 1 calc R . . H4B H 0.3139 0.7149 0.6253 0.032 Uiso 1 1 calc R . . C5 C 0.0841(2) 0.74483(15) 0.64856(13) 0.0261(5) Uani 1 1 d . . . C6 C 0.2248(2) 0.51265(15) 0.41326(12) 0.0234(4) Uani 1 1 d . . . C7 C 0.3037(2) 0.57626(15) 0.37428(13) 0.0258(5) Uani 1 1 d . . . H7 H 0.4035 0.5722 0.3804 0.031 Uiso 1 1 calc R . . C8 C 0.2364(3) 0.64567(16) 0.32641(13) 0.0288(5) Uani 1 1 d . . . H8 H 0.2895 0.6901 0.3009 0.035 Uiso 1 1 calc R . . C9 C 0.0914(2) 0.65077(16) 0.31546(13) 0.0285(5) Uani 1 1 d . . . H9 H 0.0452 0.6988 0.2831 0.034 Uiso 1 1 calc R . . C10 C 0.0155(2) 0.58515(15) 0.35222(12) 0.0252(5) Uani 1 1 d . . . H10 H -0.0823 0.5872 0.3437 0.030 Uiso 1 1 calc R . . C11 C 0.0807(2) 0.51654(15) 0.40128(12) 0.0240(4) Uani 1 1 d . . . H11 H 0.0274 0.4722 0.4267 0.029 Uiso 1 1 calc R . . C12 C 0.3287(2) 0.34294(15) 0.44855(13) 0.0247(5) Uani 1 1 d . . . H12 H 0.4240 0.3141 0.4672 0.030 Uiso 1 1 calc R . . C13 C 0.3549(2) 0.32951(15) 0.36100(13) 0.0250(5) Uani 1 1 d . . . H13A H 0.4392 0.3570 0.3351 0.030 Uiso 1 1 calc R . . H13B H 0.2652 0.3624 0.3400 0.030 Uiso 1 1 calc R . . C14 C 0.3892(2) 0.22732(15) 0.34222(14) 0.0279(5) Uani 1 1 d . . . H14A H 0.4045 0.2208 0.2849 0.033 Uiso 1 1 calc R . . H14B H 0.4819 0.1947 0.3605 0.033 Uiso 1 1 calc R . . C15 C 0.2442(3) 0.19086(15) 0.46796(13) 0.0287(5) Uani 1 1 d . . . H15A H 0.3365 0.1567 0.4859 0.034 Uiso 1 1 calc R . . H15B H 0.1619 0.1616 0.4937 0.034 Uiso 1 1 calc R . . C16 C 0.2098(2) 0.29208(15) 0.49116(13) 0.0274(5) Uani 1 1 d . . . H16A H 0.2040 0.2944 0.5483 0.033 Uiso 1 1 calc R . . H16B H 0.1116 0.3241 0.4787 0.033 Uiso 1 1 calc R . . C17 C 0.2808(2) 0.08731(15) 0.35739(14) 0.0281(5) Uani 1 1 d . . . H17A H 0.1969 0.0615 0.3865 0.034 Uiso 1 1 calc R . . H17B H 0.3744 0.0484 0.3706 0.034 Uiso 1 1 calc R . . C18 C 0.2840(3) 0.08485(16) 0.26987(14) 0.0314(5) Uani 1 1 d . . . H18A H 0.2092 0.1386 0.2544 0.038 Uiso 1 1 calc R . . H18B H 0.3832 0.0919 0.2417 0.038 Uiso 1 1 calc R . . C19 C 0.2532(2) -0.00283(15) 0.24419(13) 0.0262(5) Uani 1 1 d . . . C20 C 0.1086(3) -0.01623(17) 0.25596(15) 0.0327(5) Uani 1 1 d . . . H20 H 0.0295 0.0279 0.2840 0.039 Uiso 1 1 calc R . . C21 C 0.0786(3) -0.09287(18) 0.22739(15) 0.0359(6) Uani 1 1 d . . . H21 H -0.0208 -0.1011 0.2359 0.043 Uiso 1 1 calc R . . C22 C 0.1933(3) -0.15798(16) 0.18622(14) 0.0327(5) Uani 1 1 d . . . H22 H 0.1725 -0.2102 0.1658 0.039 Uiso 1 1 calc R . . C23 C 0.3377(3) -0.14625(16) 0.17529(14) 0.0312(5) Uani 1 1 d . . . H23 H 0.4166 -0.1908 0.1476 0.037 Uiso 1 1 calc R . . C24 C 0.3677(2) -0.06962(16) 0.20454(13) 0.0277(5) Uani 1 1 d . . . H24 H 0.4676 -0.0626 0.1975 0.033 Uiso 1 1 calc R . . O51 O -0.26782(16) 0.43003(10) 0.15797(9) 0.0275(3) Uani 1 1 d . . . O52 O -0.2179(2) 0.83869(13) 0.18450(11) 0.0422(4) Uani 1 1 d . . . O53 O -0.28302(17) 0.76125(10) 0.09664(9) 0.0274(3) Uani 1 1 d . . . N51 N -0.01688(19) 0.40882(12) 0.12850(10) 0.0231(4) Uani 1 1 d . . . N52 N 0.13591(19) 0.15080(12) 0.01044(10) 0.0224(4) Uani 1 1 d . . . H52N H 0.204(4) 0.187(2) -0.0368(19) 0.054(9) Uiso 1 1 d . . . C51 C -0.1567(2) 0.46157(15) 0.15362(12) 0.0230(4) Uani 1 1 d . . . C52 C -0.1660(2) 0.56047(15) 0.17461(13) 0.0243(4) Uani 1 1 d . . . H52A H -0.1220 0.5937 0.1279 0.029 Uiso 1 1 calc R . . H52B H -0.1058 0.5593 0.2157 0.029 Uiso 1 1 calc R . . C53 C -0.3243(2) 0.61384(15) 0.20366(13) 0.0270(5) Uani 1 1 d . . . H53A H -0.3718 0.5784 0.2477 0.032 Uiso 1 1 calc R . . H53B H -0.3827 0.6205 0.1611 0.032 Uiso 1 1 calc R . . C54 C -0.3267(2) 0.70985(15) 0.23066(13) 0.0274(5) Uani 1 1 d . . . H54A H -0.4304 0.7393 0.2538 0.033 Uiso 1 1 calc R . . H54B H -0.2661 0.7024 0.2724 0.033 Uiso 1 1 calc R . . C55 C -0.2687(2) 0.77466(15) 0.16662(13) 0.0272(5) Uani 1 1 d . . . C56 C 0.1152(2) 0.44484(14) 0.12355(13) 0.0235(4) Uani 1 1 d . . . C57 C 0.1784(2) 0.44200(15) 0.18957(13) 0.0263(5) Uani 1 1 d . . . H57 H 0.1344 0.4176 0.2380 0.032 Uiso 1 1 calc R . . C58 C 0.3067(3) 0.47511(16) 0.18433(14) 0.0300(5) Uani 1 1 d . . . H58 H 0.3507 0.4733 0.2294 0.036 Uiso 1 1 calc R . . C59 C 0.3715(2) 0.51098(16) 0.11370(14) 0.0296(5) Uani 1 1 d . . . H59 H 0.4589 0.5340 0.1106 0.036 Uiso 1 1 calc R . . C60 C 0.3079(2) 0.51299(15) 0.04766(14) 0.0292(5) Uani 1 1 d . . . H60 H 0.3523 0.5370 -0.0008 0.035 Uiso 1 1 calc R . . C61 C 0.1796(2) 0.48002(15) 0.05243(13) 0.0267(5) Uani 1 1 d . . . H61 H 0.1360 0.4814 0.0073 0.032 Uiso 1 1 calc R . . C62 C -0.0001(2) 0.31053(14) 0.11004(12) 0.0231(4) Uani 1 1 d . . . H62 H -0.0673 0.2825 0.1518 0.028 Uiso 1 1 calc R . . C63 C 0.1589(2) 0.25552(14) 0.10912(13) 0.0253(5) Uani 1 1 d . . . H63A H 0.2282 0.2846 0.0704 0.030 Uiso 1 1 calc R . . H63B H 0.1855 0.2570 0.1613 0.030 Uiso 1 1 calc R . . C64 C 0.1760(2) 0.15534(15) 0.08829(13) 0.0260(5) Uani 1 1 d . . . H64A H 0.2803 0.1213 0.0877 0.031 Uiso 1 1 calc R . . H64B H 0.1108 0.1252 0.1285 0.031 Uiso 1 1 calc R . . C65 C -0.0222(2) 0.20075(15) 0.01143(13) 0.0249(5) Uani 1 1 d . . . H65A H -0.0888 0.1703 0.0506 0.030 Uiso 1 1 calc R . . H65B H -0.0486 0.1976 -0.0405 0.030 Uiso 1 1 calc R . . C66 C -0.0447(2) 0.30184(15) 0.03156(13) 0.0241(4) Uani 1 1 d . . . H66A H -0.1506 0.3331 0.0336 0.029 Uiso 1 1 calc R . . H66B H 0.0158 0.3334 -0.0100 0.029 Uiso 1 1 calc R . . C67 C 0.1601(2) 0.05366(14) -0.01357(13) 0.0252(5) Uani 1 1 d . . . H67A H 0.1147 0.0533 -0.0603 0.030 Uiso 1 1 calc R . . H67B H 0.1094 0.0179 0.0290 0.030 Uiso 1 1 calc R . . C68 C 0.3254(2) 0.00631(15) -0.03219(13) 0.0254(5) Uani 1 1 d . . . H68A H 0.3810 0.0495 -0.0640 0.030 Uiso 1 1 calc R . . H68B H 0.3648 -0.0088 0.0172 0.030 Uiso 1 1 calc R . . C69 C 0.3496(2) -0.08145(15) -0.07619(13) 0.0248(5) Uani 1 1 d . . . C70 C 0.4172(2) -0.16695(16) -0.04542(14) 0.0282(5) Uani 1 1 d . . . H70 H 0.4509 -0.1698 0.0030 0.034 Uiso 1 1 calc R . . C71 C 0.4355(2) -0.24801(16) -0.08503(15) 0.0312(5) Uani 1 1 d . . . H71 H 0.4823 -0.3057 -0.0638 0.037 Uiso 1 1 calc R . . C72 C 0.3859(2) -0.24486(16) -0.15528(14) 0.0307(5) Uani 1 1 d . . . H72 H 0.3970 -0.3003 -0.1819 0.037 Uiso 1 1 calc R . . C73 C 0.3199(2) -0.16007(16) -0.18659(14) 0.0299(5) Uani 1 1 d . . . H73 H 0.2858 -0.1574 -0.2348 0.036 Uiso 1 1 calc R . . C74 C 0.3036(2) -0.07901(16) -0.14738(13) 0.0275(5) Uani 1 1 d . . . H74 H 0.2602 -0.0211 -0.1698 0.033 Uiso 1 1 calc R . . O4 O 0.4332(2) 0.87427(15) 0.44850(13) 0.0562(5) Uani 1 1 d . . . H4O H 0.5038 0.8816 0.4127 0.067 Uiso 1 1 calc R . . C75 C 0.3539(4) 0.8161(2) 0.42325(19) 0.0523(7) Uani 1 1 d . . . H75A H 0.2672 0.8112 0.4635 0.078 Uiso 1 1 calc R . . H75B H 0.4187 0.7544 0.4140 0.078 Uiso 1 1 calc R . . H75C H 0.3205 0.8421 0.3746 0.078 Uiso 1 1 calc R . . O5 O 0.2984(3) 0.92345(17) 0.60162(15) 0.0595(6) Uani 1 1 d D . . H51O H 0.223(3) 0.898(2) 0.6145(18) 0.071 Uiso 1 1 d D . . H52O H 0.329(4) 0.907(3) 0.5536(9) 0.071 Uiso 1 1 d D . . O6 O 0.6754(4) 0.9114(2) 0.34158(16) 0.0839(9) Uani 1 1 d D . . H61O H 0.705(5) 0.958(2) 0.355(2) 0.101 Uiso 1 1 d D . . H62O H 0.705(5) 0.900(3) 0.2941(9) 0.101 Uiso 1 1 d 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 O1 0.0247(8) 0.0253(8) 0.0287(8) -0.0026(6) -0.0088(6) -0.0045(6) O2 0.0279(9) 0.0263(9) 0.0786(14) 0.0007(9) -0.0071(9) -0.0062(7) O3 0.0220(8) 0.0302(8) 0.0425(9) -0.0014(7) -0.0080(7) -0.0075(6) N1 0.0204(9) 0.0237(9) 0.0244(9) -0.0051(7) -0.0064(7) -0.0037(7) N2 0.0211(9) 0.0231(9) 0.0307(10) -0.0061(7) -0.0065(8) -0.0032(7) C1 0.0148(9) 0.0271(11) 0.0230(10) -0.0044(8) -0.0020(8) -0.0064(8) C2 0.0207(10) 0.0226(10) 0.0237(11) -0.0033(8) -0.0049(8) -0.0053(8) C3 0.0206(10) 0.0243(11) 0.0272(11) -0.0052(8) -0.0059(8) -0.0037(8) C4 0.0230(11) 0.0286(12) 0.0295(11) -0.0073(9) -0.0060(9) -0.0072(9) C5 0.0221(11) 0.0278(12) 0.0288(11) -0.0084(9) -0.0015(9) -0.0066(9) C6 0.0223(10) 0.0276(11) 0.0210(10) -0.0059(8) -0.0038(8) -0.0052(8) C7 0.0207(10) 0.0305(12) 0.0272(11) -0.0058(9) -0.0044(8) -0.0056(9) C8 0.0297(12) 0.0313(12) 0.0275(11) -0.0019(9) -0.0047(9) -0.0108(9) C9 0.0290(12) 0.0304(12) 0.0260(11) -0.0028(9) -0.0068(9) -0.0042(9) C10 0.0198(10) 0.0319(12) 0.0242(11) -0.0060(9) -0.0041(8) -0.0046(9) C11 0.0214(10) 0.0271(11) 0.0233(10) -0.0054(8) -0.0025(8) -0.0048(8) C12 0.0203(10) 0.0224(11) 0.0318(12) -0.0067(9) -0.0074(9) -0.0011(8) C13 0.0198(10) 0.0272(11) 0.0288(11) -0.0072(9) -0.0028(8) -0.0059(8) C14 0.0201(10) 0.0297(12) 0.0346(12) -0.0102(9) -0.0031(9) -0.0058(9) C15 0.0329(12) 0.0253(12) 0.0292(12) -0.0040(9) -0.0080(9) -0.0061(9) C16 0.0284(11) 0.0254(11) 0.0294(11) -0.0055(9) -0.0057(9) -0.0058(9) C17 0.0264(11) 0.0235(11) 0.0354(12) -0.0066(9) -0.0089(9) -0.0029(9) C18 0.0340(12) 0.0291(12) 0.0325(12) -0.0055(10) -0.0052(10) -0.0090(10) C19 0.0267(11) 0.0271(11) 0.0266(11) -0.0027(9) -0.0078(9) -0.0066(9) C20 0.0266(11) 0.0305(12) 0.0401(13) -0.0038(10) -0.0063(10) -0.0033(9) C21 0.0279(12) 0.0398(14) 0.0448(14) -0.0014(11) -0.0105(10) -0.0138(10) C22 0.0429(14) 0.0277(12) 0.0330(12) -0.0009(10) -0.0132(10) -0.0136(10) C23 0.0365(13) 0.0280(12) 0.0287(12) -0.0038(9) -0.0063(10) -0.0049(9) C24 0.0241(11) 0.0310(12) 0.0284(11) -0.0016(9) -0.0063(9) -0.0057(9) O51 0.0231(8) 0.0267(8) 0.0343(8) -0.0048(6) -0.0036(6) -0.0084(6) O52 0.0549(11) 0.0413(10) 0.0419(10) 0.0018(8) -0.0174(8) -0.0274(9) O53 0.0284(8) 0.0266(8) 0.0284(8) -0.0032(6) -0.0030(6) -0.0093(6) N51 0.0210(9) 0.0214(9) 0.0276(9) -0.0043(7) -0.0046(7) -0.0049(7) N52 0.0193(8) 0.0210(9) 0.0277(9) -0.0056(7) -0.0040(7) -0.0051(7) C51 0.0246(11) 0.0246(11) 0.0208(10) -0.0014(8) -0.0052(8) -0.0066(9) C52 0.0230(10) 0.0245(11) 0.0259(11) -0.0029(8) -0.0044(8) -0.0055(8) C53 0.0244(11) 0.0268(11) 0.0295(11) -0.0017(9) -0.0019(9) -0.0074(9) C54 0.0242(11) 0.0270(11) 0.0290(11) -0.0057(9) -0.0025(9) -0.0021(9) C55 0.0242(11) 0.0250(11) 0.0331(12) -0.0043(9) -0.0083(9) -0.0036(9) C56 0.0198(10) 0.0211(10) 0.0294(11) -0.0054(8) -0.0038(8) -0.0033(8) C57 0.0271(11) 0.0266(11) 0.0254(11) -0.0042(9) -0.0051(9) -0.0048(9) C58 0.0286(11) 0.0314(12) 0.0327(12) -0.0089(10) -0.0098(10) -0.0062(9) C59 0.0213(11) 0.0287(12) 0.0401(13) -0.0084(10) -0.0047(9) -0.0061(9) C60 0.0248(11) 0.0265(11) 0.0349(12) 0.0003(9) -0.0031(9) -0.0051(9) C61 0.0240(11) 0.0270(11) 0.0296(11) -0.0023(9) -0.0079(9) -0.0039(9) C62 0.0232(10) 0.0220(11) 0.0249(11) -0.0033(8) -0.0040(8) -0.0062(8) C63 0.0261(11) 0.0214(11) 0.0309(11) -0.0058(9) -0.0107(9) -0.0042(8) C64 0.0273(11) 0.0224(11) 0.0292(11) -0.0030(9) -0.0089(9) -0.0037(8) C65 0.0206(10) 0.0280(11) 0.0279(11) -0.0054(9) -0.0063(8) -0.0059(8) C66 0.0197(10) 0.0243(11) 0.0278(11) -0.0039(8) -0.0041(8) -0.0029(8) C67 0.0230(10) 0.0213(11) 0.0325(12) -0.0050(9) -0.0037(9) -0.0072(8) C68 0.0218(10) 0.0238(11) 0.0317(12) -0.0053(9) -0.0061(9) -0.0048(8) C69 0.0166(10) 0.0252(11) 0.0323(12) -0.0038(9) -0.0010(8) -0.0059(8) C70 0.0244(11) 0.0281(12) 0.0327(12) -0.0033(9) -0.0053(9) -0.0059(9) C71 0.0244(11) 0.0246(11) 0.0423(13) -0.0027(10) -0.0006(10) -0.0045(9) C72 0.0227(11) 0.0277(12) 0.0412(13) -0.0102(10) 0.0029(10) -0.0088(9) C73 0.0242(11) 0.0333(12) 0.0335(12) -0.0078(10) -0.0030(9) -0.0085(9) C74 0.0237(11) 0.0254(11) 0.0328(12) -0.0029(9) -0.0021(9) -0.0063(9) O4 0.0494(12) 0.0635(14) 0.0601(13) -0.0037(11) -0.0073(10) -0.0227(10) C75 0.0611(19) 0.0472(17) 0.0538(18) 0.0019(14) -0.0151(15) -0.0199(14) O5 0.0494(13) 0.0651(14) 0.0710(15) -0.0004(12) -0.0114(11) -0.0267(11) O6 0.103(2) 0.096(2) 0.0604(16) -0.0325(15) 0.0147(15) -0.0520(17) _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 1.231(3) . ? O2 C5 1.250(3) . ? O3 C5 1.267(3) . ? N1 C1 1.371(3) . ? N1 C6 1.444(3) . ? N1 C12 1.488(3) . ? N2 H2N 0.93(3) . ? N2 C14 1.494(3) . ? N2 C15 1.491(3) . ? N2 C17 1.500(3) . ? C1 C2 1.521(3) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C2 C3 1.523(3) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.528(3) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C4 C5 1.525(3) . ? C6 C7 1.390(3) . ? C6 C11 1.394(3) . ? C7 H7 0.950 . ? C7 C8 1.387(3) . ? C8 H8 0.950 . ? C8 C9 1.393(3) . ? C9 H9 0.950 . ? C9 C10 1.384(3) . ? C10 H10 0.950 . ? C10 C11 1.386(3) . ? C11 H11 0.950 . ? C12 H12 1.000 . ? C12 C13 1.519(3) . ? C12 C16 1.534(3) . ? C13 H13A 0.990 . ? C13 H13B 0.990 . ? C13 C14 1.522(3) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C15 C16 1.529(3) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C17 C18 1.522(3) . ? C18 H18A 0.990 . ? C18 H18B 0.990 . ? C18 C19 1.512(3) . ? C19 C20 1.390(3) . ? C19 C24 1.393(3) . ? C20 H20 0.950 . ? C20 C21 1.381(3) . ? C21 H21 0.950 . ? C21 C22 1.391(4) . ? C22 H22 0.950 . ? C22 C23 1.380(3) . ? C23 H23 0.950 . ? C23 C24 1.386(3) . ? C24 H24 0.950 . ? O51 C51 1.226(3) . ? O52 C55 1.240(3) . ? O53 C55 1.287(3) . ? N51 C51 1.371(3) . ? N51 C56 1.444(3) . ? N51 C62 1.483(3) . ? N52 H52N 1.13(3) . ? N52 C64 1.485(3) . ? N52 C65 1.494(3) . ? N52 C67 1.485(3) . ? C51 C52 1.517(3) . ? C52 H52A 0.990 . ? C52 H52B 0.990 . ? C52 C53 1.522(3) . ? C53 H53A 0.990 . ? C53 H53B 0.990 . ? C53 C54 1.527(3) . ? C54 H54A 0.990 . ? C54 H54B 0.990 . ? C54 C55 1.521(3) . ? C56 C57 1.385(3) . ? C56 C61 1.391(3) . ? C57 H57 0.950 . ? C57 C58 1.386(3) . ? C58 H58 0.950 . ? C58 C59 1.390(3) . ? C59 H59 0.950 . ? C59 C60 1.389(3) . ? C60 H60 0.950 . ? C60 C61 1.386(3) . ? C61 H61 0.950 . ? C62 H62 1.000 . ? C62 C63 1.523(3) . ? C62 C66 1.527(3) . ? C63 H63A 0.990 . ? C63 H63B 0.990 . ? C63 C64 1.521(3) . ? C64 H64A 0.990 . ? C64 H64B 0.990 . ? C65 H65A 0.990 . ? C65 H65B 0.990 . ? C65 C66 1.523(3) . ? C66 H66A 0.990 . ? C66 H66B 0.990 . ? C67 H67A 0.990 . ? C67 H67B 0.990 . ? C67 C68 1.530(3) . ? C68 H68A 0.990 . ? C68 H68B 0.990 . ? C68 C69 1.510(3) . ? C69 C70 1.397(3) . ? C69 C74 1.385(3) . ? C70 H70 0.950 . ? C70 C71 1.391(3) . ? C71 H71 0.950 . ? C71 C72 1.384(4) . ? C72 H72 0.950 . ? C72 C73 1.388(3) . ? C73 H73 0.950 . ? C73 C74 1.391(3) . ? C74 H74 0.950 . ? O4 H4O 0.840 . ? O4 C75 1.403(3) . ? C75 H75A 0.980 . ? C75 H75B 0.980 . ? C75 H75C 0.980 . ? O5 H51O 0.863(10) . ? O5 H52O 0.866(10) . ? O6 H61O 0.855(10) . ? O6 H62O 0.838(10) . ? 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 121.10(17) . . ? C1 N1 C12 117.75(17) . . ? C6 N1 C12 121.13(17) . . ? H2N N2 C14 105.2(17) . . ? H2N N2 C15 108.0(17) . . ? H2N N2 C17 109.0(17) . . ? C14 N2 C15 109.82(16) . . ? C14 N2 C17 112.63(17) . . ? C15 N2 C17 111.86(17) . . ? O1 C1 N1 120.67(19) . . ? O1 C1 C2 121.28(18) . . ? N1 C1 C2 118.05(18) . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C1 C2 C3 112.65(17) . . ? H2A C2 H2B 107.8 . . ? H2A C2 C3 109.1 . . ? H2B C2 C3 109.1 . . ? C2 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C2 C3 C4 112.44(18) . . ? H3A C3 H3B 107.8 . . ? H3A C3 C4 109.1 . . ? H3B C3 C4 109.1 . . ? C3 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C3 C4 C5 115.53(17) . . ? H4A C4 H4B 107.5 . . ? H4A C4 C5 108.4 . . ? H4B C4 C5 108.4 . . ? O2 C5 O3 123.4(2) . . ? O2 C5 C4 118.88(19) . . ? O3 C5 C4 117.7(2) . . ? N1 C6 C7 120.34(18) . . ? N1 C6 C11 119.94(18) . . ? C7 C6 C11 119.7(2) . . ? C6 C7 H7 120.1 . . ? C6 C7 C8 119.9(2) . . ? H7 C7 C8 120.1 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.5(2) . . ? H8 C8 C9 119.8 . . ? C8 C9 H9 120.3 . . ? C8 C9 C10 119.3(2) . . ? H9 C9 C10 120.3 . . ? C9 C10 H10 119.7 . . ? C9 C10 C11 120.6(2) . . ? H10 C10 C11 119.7 . . ? C6 C11 C10 119.89(19) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N1 C12 H12 107.6 . . ? N1 C12 C13 111.15(18) . . ? N1 C12 C16 112.35(17) . . ? H12 C12 C13 107.6 . . ? H12 C12 C16 107.6 . . ? C13 C12 C16 110.40(17) . . ? C12 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? C12 C13 C14 111.58(18) . . ? H13A C13 H13B 108.0 . . ? H13A C13 C14 109.3 . . ? H13B C13 C14 109.3 . . ? N2 C14 C13 109.81(17) . . ? N2 C14 H14A 109.7 . . ? N2 C14 H14B 109.7 . . ? C13 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? N2 C15 C16 110.52(18) . . ? H15A C15 H15B 108.1 . . ? H15A C15 C16 109.5 . . ? H15B C15 C16 109.5 . . ? C12 C16 C15 111.88(18) . . ? C12 C16 H16A 109.2 . . ? C12 C16 H16B 109.2 . . ? C15 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? N2 C17 C18 110.58(18) . . ? H17A C17 H17B 108.1 . . ? H17A C17 C18 109.5 . . ? H17B C17 C18 109.5 . . ? C17 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C17 C18 C19 114.30(19) . . ? H18A C18 H18B 107.6 . . ? H18A C18 C19 108.7 . . ? H18B C18 C19 108.7 . . ? C18 C19 C20 120.7(2) . . ? C18 C19 C24 120.7(2) . . ? C20 C19 C24 118.5(2) . . ? C19 C20 H20 119.6 . . ? C19 C20 C21 120.8(2) . . ? H20 C20 C21 119.6 . . ? C20 C21 H21 119.9 . . ? C20 C21 C22 120.2(2) . . ? H21 C21 C22 119.9 . . ? C21 C22 H22 120.2 . . ? C21 C22 C23 119.6(2) . . ? H22 C22 C23 120.2 . . ? C22 C23 H23 119.9 . . ? C22 C23 C24 120.2(2) . . ? H23 C23 C24 119.9 . . ? C19 C24 C23 120.7(2) . . ? C19 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C51 N51 C56 121.83(17) . . ? C51 N51 C62 119.14(17) . . ? C56 N51 C62 118.95(16) . . ? H52N N52 C64 112.0(16) . . ? H52N N52 C65 105.5(16) . . ? H52N N52 C67 106.8(16) . . ? C64 N52 C65 109.76(16) . . ? C64 N52 C67 111.90(17) . . ? C65 N52 C67 110.66(15) . . ? O51 C51 N51 121.20(19) . . ? O51 C51 C52 122.18(19) . . ? N51 C51 C52 116.62(17) . . ? C51 C52 H52A 108.9 . . ? C51 C52 H52B 108.9 . . ? C51 C52 C53 113.53(17) . . ? H52A C52 H52B 107.7 . . ? H52A C52 C53 108.9 . . ? H52B C52 C53 108.9 . . ? C52 C53 H53A 109.3 . . ? C52 C53 H53B 109.3 . . ? C52 C53 C54 111.52(17) . . ? H53A C53 H53B 108.0 . . ? H53A C53 C54 109.3 . . ? H53B C53 C54 109.3 . . ? C53 C54 H54A 108.6 . . ? C53 C54 H54B 108.6 . . ? C53 C54 C55 114.77(18) . . ? H54A C54 H54B 107.6 . . ? H54A C54 C55 108.6 . . ? H54B C54 C55 108.6 . . ? O52 C55 O53 124.2(2) . . ? O52 C55 C54 119.3(2) . . ? O53 C55 C54 116.43(18) . . ? N51 C56 C57 119.45(19) . . ? N51 C56 C61 119.93(19) . . ? C57 C56 C61 120.59(19) . . ? C56 C57 H57 120.3 . . ? C56 C57 C58 119.3(2) . . ? H57 C57 C58 120.3 . . ? C57 C58 H58 119.7 . . ? C57 C58 C59 120.6(2) . . ? H58 C58 C59 119.7 . . ? C58 C59 H59 120.1 . . ? C58 C59 C60 119.7(2) . . ? H59 C59 C60 120.1 . . ? C59 C60 H60 120.0 . . ? C59 C60 C61 120.1(2) . . ? H60 C60 C61 120.0 . . ? C56 C61 C60 119.7(2) . . ? C56 C61 H61 120.1 . . ? C60 C61 H61 120.1 . . ? N51 C62 H62 108.1 . . ? N51 C62 C63 111.44(16) . . ? N51 C62 C66 111.70(17) . . ? H62 C62 C63 108.1 . . ? H62 C62 C66 108.1 . . ? C63 C62 C66 109.22(17) . . ? C62 C63 H63A 109.4 . . ? C62 C63 H63B 109.4 . . ? C62 C63 C64 111.09(17) . . ? H63A C63 H63B 108.0 . . ? H63A C63 C64 109.4 . . ? H63B C63 C64 109.4 . . ? N52 C64 C63 110.69(17) . . ? N52 C64 H64A 109.5 . . ? N52 C64 H64B 109.5 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 108.1 . . ? N52 C65 H65A 109.5 . . ? N52 C65 H65B 109.5 . . ? N52 C65 C66 110.56(16) . . ? H65A C65 H65B 108.1 . . ? H65A C65 C66 109.5 . . ? H65B C65 C66 109.5 . . ? C62 C66 C65 111.58(18) . . ? C62 C66 H66A 109.3 . . ? C62 C66 H66B 109.3 . . ? C65 C66 H66A 109.3 . . ? C65 C66 H66B 109.3 . . ? H66A C66 H66B 108.0 . . ? N52 C67 H67A 109.1 . . ? N52 C67 H67B 109.1 . . ? N52 C67 C68 112.35(16) . . ? H67A C67 H67B 107.9 . . ? H67A C67 C68 109.1 . . ? H67B C67 C68 109.1 . . ? C67 C68 H68A 109.4 . . ? C67 C68 H68B 109.4 . . ? C67 C68 C69 111.38(17) . . ? H68A C68 H68B 108.0 . . ? H68A C68 C69 109.4 . . ? H68B C68 C69 109.4 . . ? C68 C69 C70 120.7(2) . . ? C68 C69 C74 120.7(2) . . ? C70 C69 C74 118.6(2) . . ? C69 C70 H70 119.7 . . ? C69 C70 C71 120.6(2) . . ? H70 C70 C71 119.7 . . ? C70 C71 H71 119.9 . . ? C70 C71 C72 120.2(2) . . ? H71 C71 C72 119.9 . . ? C71 C72 H72 120.2 . . ? C71 C72 C73 119.5(2) . . ? H72 C72 C73 120.2 . . ? C72 C73 H73 120.0 . . ? C72 C73 C74 120.1(2) . . ? H73 C73 C74 120.0 . . ? C69 C74 C73 121.0(2) . . ? C69 C74 H74 119.5 . . ? C73 C74 H74 119.5 . . ? H4O O4 C75 109.5 . . ? O4 C75 H75A 109.5 . . ? O4 C75 H75B 109.5 . . ? O4 C75 H75C 109.5 . . ? H75A C75 H75B 109.5 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? H51O O5 H52O 101(2) . . ? H61O O6 H62O 112(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 C6 N1 C1 O1 178.89(17) . . . . ? C6 N1 C1 C2 -1.5(3) . . . . ? C12 N1 C1 O1 0.7(3) . . . . ? C12 N1 C1 C2 -179.69(17) . . . . ? O1 C1 C2 C3 -18.2(3) . . . . ? N1 C1 C2 C3 162.17(17) . . . . ? C1 C2 C3 C4 176.58(16) . . . . ? C2 C3 C4 C5 68.0(2) . . . . ? C3 C4 C5 O2 -150.2(2) . . . . ? C3 C4 C5 O3 30.5(3) . . . . ? C1 N1 C6 C7 68.7(3) . . . . ? C1 N1 C6 C11 -110.9(2) . . . . ? C12 N1 C6 C7 -113.2(2) . . . . ? C12 N1 C6 C11 67.3(3) . . . . ? N1 C6 C7 C8 -176.74(19) . . . . ? C11 C6 C7 C8 2.8(3) . . . . ? C6 C7 C8 C9 -1.7(3) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C11 1.9(3) . . . . ? C9 C10 C11 C6 -0.7(3) . . . . ? N1 C6 C11 C10 177.91(19) . . . . ? C7 C6 C11 C10 -1.7(3) . . . . ? C1 N1 C12 C13 -156.57(17) . . . . ? C1 N1 C12 C16 79.2(2) . . . . ? C6 N1 C12 C13 25.3(2) . . . . ? C6 N1 C12 C16 -99.0(2) . . . . ? N1 C12 C13 C14 -178.38(16) . . . . ? C16 C12 C13 C14 -53.0(2) . . . . ? C15 N2 C14 C13 -61.8(2) . . . . ? C17 N2 C14 C13 172.80(18) . . . . ? C12 C13 C14 N2 58.7(2) . . . . ? C14 N2 C15 C16 60.3(2) . . . . ? C17 N2 C15 C16 -173.89(17) . . . . ? N2 C15 C16 C12 -55.3(2) . . . . ? N1 C12 C16 C15 175.99(17) . . . . ? C13 C12 C16 C15 51.3(2) . . . . ? C14 N2 C17 C18 -61.5(2) . . . . ? C15 N2 C17 C18 174.25(18) . . . . ? N2 C17 C18 C19 -161.85(18) . . . . ? C17 C18 C19 C20 77.4(3) . . . . ? C17 C18 C19 C24 -106.1(2) . . . . ? C18 C19 C20 C21 175.1(2) . . . . ? C24 C19 C20 C21 -1.6(4) . . . . ? C19 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C23 1.1(4) . . . . ? C21 C22 C23 C24 -0.6(4) . . . . ? C22 C23 C24 C19 -1.0(3) . . . . ? C18 C19 C24 C23 -174.6(2) . . . . ? C20 C19 C24 C23 2.0(3) . . . . ? C56 N51 C51 O51 -179.6(2) . . . . ? C56 N51 C51 C52 1.1(3) . . . . ? C62 N51 C51 O51 -3.0(3) . . . . ? C62 N51 C51 C52 177.67(18) . . . . ? O51 C51 C52 C53 2.0(3) . . . . ? N51 C51 C52 C53 -178.71(18) . . . . ? C51 C52 C53 C54 175.06(18) . . . . ? C52 C53 C54 C55 63.9(2) . . . . ? C53 C54 C55 O52 -155.2(2) . . . . ? C53 C54 C55 O53 28.1(3) . . . . ? C51 N51 C56 C57 84.6(3) . . . . ? C51 N51 C56 C61 -96.9(2) . . . . ? C62 N51 C56 C57 -92.1(2) . . . . ? C62 N51 C56 C61 86.5(2) . . . . ? N51 C56 C57 C58 178.86(19) . . . . ? C61 C56 C57 C58 0.4(3) . . . . ? C56 C57 C58 C59 0.1(3) . . . . ? C57 C58 C59 C60 -0.5(3) . . . . ? C58 C59 C60 C61 0.5(3) . . . . ? C59 C60 C61 C56 -0.1(3) . . . . ? N51 C56 C61 C60 -178.9(2) . . . . ? C57 C56 C61 C60 -0.4(3) . . . . ? C51 N51 C62 C63 -161.54(18) . . . . ? C51 N51 C62 C66 76.0(2) . . . . ? C56 N51 C62 C63 15.2(3) . . . . ? C56 N51 C62 C66 -107.3(2) . . . . ? N51 C62 C63 C64 -178.69(17) . . . . ? C66 C62 C63 C64 -54.8(2) . . . . ? C65 N52 C64 C63 -60.1(2) . . . . ? C67 N52 C64 C63 176.63(17) . . . . ? C62 C63 C64 N52 58.7(2) . . . . ? C64 N52 C65 C66 59.2(2) . . . . ? C67 N52 C65 C66 -176.79(17) . . . . ? N52 C65 C66 C62 -57.1(2) . . . . ? N51 C62 C66 C65 178.03(16) . . . . ? C63 C62 C66 C65 54.3(2) . . . . ? C64 N52 C67 C68 -69.4(2) . . . . ? C65 N52 C67 C68 167.85(18) . . . . ? N52 C67 C68 C69 -164.98(18) . . . . ? C67 C68 C69 C70 -120.4(2) . . . . ? C67 C68 C69 C74 58.8(3) . . . . ? C68 C69 C70 C71 178.18(19) . . . . ? C74 C69 C70 C71 -1.0(3) . . . . ? C69 C70 C71 C72 -0.5(3) . . . . ? C70 C71 C72 C73 1.1(3) . . . . ? C71 C72 C73 C74 -0.1(3) . . . . ? C68 C69 C74 C73 -177.26(19) . . . . ? C70 C69 C74 C73 1.9(3) . . . . ? C72 C73 C74 C69 -1.4(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 N2 H2N O3 0.93(3) 1.72(3) 2.648(2) 176(3) 2_566 N2 H2N O2 0.93(3) 2.61(3) 3.230(2) 125(2) 2_566 N52 H52N O53 1.13(3) 1.44(3) 2.563(2) 176(3) 2_565 N52 H52N O52 1.13(3) 2.60(3) 3.336(3) 122(2) 2_565 O4 H4O O6 0.84 1.95 2.783(3) 170.6 . O5 H51O O2 0.863(10) 1.909(12) 2.764(3) 171(3) . O5 H52O O4 0.866(10) 1.942(11) 2.798(3) 169(3) . O6 H61O O5 0.855(10) 1.966(17) 2.788(4) 161(4) 2_676 O6 H62O O52 0.838(10) 2.104(14) 2.925(3) 167(4) 1_655 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 67.77 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.566 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.053 #===END OF CIF