data_gellman142 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 N2 O5' _chemical_formula_weight 404.50 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.041(3) _cell_length_b 10.187(6) _cell_length_c 10.943(7) _cell_angle_alpha 92.56(3) _cell_angle_beta 95.52(4) _cell_angle_gamma 101.11(4) _cell_volume 547.7(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.64 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3904 _exptl_absorpt_correction_T_max 0.8835 _exptl_absorpt_process_details ? _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' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11924 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 69.46 _reflns_number_total 3389 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0596P)^2^+0.0798P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(13) _refine_ls_number_reflns 3389 _refine_ls_number_parameters 275 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _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 0.2417(2) -0.06098(11) 0.45890(9) 0.0240(2) Uani 1 1 d . . . O2 O 0.6033(2) 0.10751(11) 0.43762(10) 0.0244(2) Uani 1 1 d . . . O3 O 0.2604(2) 0.06929(10) 0.09661(9) 0.0222(2) Uani 1 1 d . . . O4 O 0.1609(2) -0.11532(11) -0.16130(10) 0.0270(3) Uani 1 1 d . . . O5 O -0.0095(2) 0.07291(10) -0.15186(9) 0.0233(2) Uani 1 1 d . . . N1 N 0.1756(3) 0.14520(12) 0.43876(11) 0.0192(3) Uani 1 1 d D . . H1 H 0.0036(13) 0.1057(19) 0.4357(19) 0.028(5) Uiso 1 1 d D . . N2 N -0.1956(3) 0.01155(12) 0.06391(10) 0.0185(3) Uani 1 1 d D . . H2 H -0.3559(17) 0.0301(18) 0.0737(17) 0.024(5) Uiso 1 1 d D . . C1 C 0.5458(4) -0.17960(16) 0.35437(14) 0.0268(3) Uani 1 1 d . . . H1B H 0.6934 -0.1018 0.3520 0.040 Uiso 1 1 calc R . . H1A H 0.4139 -0.1842 0.2817 0.040 Uiso 1 1 calc R . . H1C H 0.6205 -0.2616 0.3550 0.040 Uiso 1 1 calc R . . C2 C 0.1902(4) -0.29106(18) 0.4800(2) 0.0380(4) Uani 1 1 d . . . H2A H 0.0684 -0.3094 0.4032 0.057 Uiso 1 1 calc R . . H2B H 0.0850 -0.2771 0.5485 0.057 Uiso 1 1 calc R . . H2C H 0.2788 -0.3674 0.4945 0.057 Uiso 1 1 calc R . . C3 C 0.6004(4) -0.1367(2) 0.58790(15) 0.0327(4) Uani 1 1 d . . . H3B H 0.4993 -0.1218 0.6577 0.049 Uiso 1 1 calc R . . H3A H 0.7386 -0.0564 0.5800 0.049 Uiso 1 1 calc R . . H3C H 0.6890 -0.2132 0.6016 0.049 Uiso 1 1 calc R . . C4 C 0.4051(3) -0.16582(15) 0.47033(14) 0.0248(3) Uani 1 1 d . . . C5 C 0.3612(3) 0.06705(15) 0.44365(12) 0.0190(3) Uani 1 1 d . . . C6 C 0.2408(3) 0.28311(14) 0.40418(13) 0.0213(3) Uani 1 1 d . . . H6B H 0.4166 0.3281 0.4495 0.026 Uiso 1 1 calc R . . H6A H 0.0994 0.3312 0.4287 0.026 Uiso 1 1 calc R . . C7 C 0.2592(3) 0.29222(13) 0.26605(13) 0.0192(3) Uani 1 1 d . . . H7 H 0.4184 0.2550 0.2429 0.023 Uiso 1 1 calc R . . C8 C 0.2889(4) 0.43842(15) 0.22840(15) 0.0262(3) Uani 1 1 d . . . H8B H 0.3565 0.5025 0.3004 0.031 Uiso 1 1 calc R . . H8A H 0.4162 0.4559 0.1649 0.031 Uiso 1 1 calc R . . C9 C 0.0027(4) 0.45052(15) 0.17755(15) 0.0278(4) Uani 1 1 d . . . H9B H 0.0071 0.5265 0.1239 0.033 Uiso 1 1 calc R . . H9A H -0.1104 0.4625 0.2447 0.033 Uiso 1 1 calc R . . C10 C -0.1030(3) 0.31668(15) 0.10417(13) 0.0236(3) Uani 1 1 d . . . H10A H -0.0252 0.3151 0.0246 0.028 Uiso 1 1 calc R . . H10B H -0.3039 0.2980 0.0886 0.028 Uiso 1 1 calc R . . C11 C -0.0033(3) 0.21448(14) 0.18984(12) 0.0178(3) Uani 1 1 d . . . H11 H -0.1436 0.1856 0.2470 0.021 Uiso 1 1 calc R . . C12 C 0.0360(3) 0.09174(14) 0.11482(12) 0.0181(3) Uani 1 1 d . . . C13 C -0.1856(3) -0.09799(15) -0.02534(13) 0.0209(3) Uani 1 1 d . . . H13 H -0.3708 -0.1258 -0.0713 0.025 Uiso 1 1 calc R . . C14 C -0.1160(4) -0.22048(15) 0.03599(14) 0.0263(3) Uani 1 1 d . . . H14C H -0.2545 -0.2537 0.0902 0.040 Uiso 1 1 calc R . . H14A H 0.0622 -0.1955 0.0844 0.040 Uiso 1 1 calc R . . H14B H -0.1110 -0.2909 -0.0273 0.040 Uiso 1 1 calc R . . C15 C 0.0129(3) -0.04973(14) -0.11911(12) 0.0208(3) Uani 1 1 d . . . C16 C 0.1915(4) 0.13645(17) -0.22984(15) 0.0291(4) Uani 1 1 d . . . H16B H 0.1585 0.0911 -0.3134 0.035 Uiso 1 1 calc R . . H16A H 0.3776 0.1321 -0.1943 0.035 Uiso 1 1 calc R . . C17 C 0.1583(3) 0.27931(15) -0.23470(13) 0.0257(4) Uani 1 1 d . . . C18 C -0.0535(4) 0.31275(16) -0.30958(14) 0.0293(4) Uani 1 1 d . . . H18 H -0.1736 0.2449 -0.3613 0.035 Uiso 1 1 calc R . . C19 C -0.0921(4) 0.44351(18) -0.31000(16) 0.0366(4) Uani 1 1 d . . . H19 H -0.2380 0.4649 -0.3618 0.044 Uiso 1 1 calc R . . C20 C 0.0809(5) 0.54287(18) -0.23521(17) 0.0416(5) Uani 1 1 d . . . H20 H 0.0533 0.6325 -0.2352 0.050 Uiso 1 1 calc R . . C21 C 0.2918(5) 0.5125(2) -0.16109(17) 0.0459(6) Uani 1 1 d . . . H21 H 0.4108 0.5811 -0.1097 0.055 Uiso 1 1 calc R . . C22 C 0.3327(4) 0.38041(19) -0.16071(16) 0.0381(4) Uani 1 1 d . . . H22 H 0.4805 0.3598 -0.1096 0.046 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 0.0167(6) 0.0252(5) 0.0311(5) 0.0075(4) 0.0050(4) 0.0043(4) O2 0.0164(6) 0.0273(5) 0.0285(5) 0.0005(4) 0.0023(4) 0.0027(4) O3 0.0165(6) 0.0254(5) 0.0254(5) -0.0024(4) 0.0039(4) 0.0066(4) O4 0.0313(7) 0.0259(5) 0.0258(5) -0.0021(4) 0.0067(4) 0.0092(5) O5 0.0266(6) 0.0249(5) 0.0208(5) 0.0056(4) 0.0070(4) 0.0081(4) N1 0.0137(7) 0.0244(6) 0.0194(5) 0.0022(4) 0.0026(4) 0.0027(5) N2 0.0149(7) 0.0209(6) 0.0211(6) 0.0028(4) 0.0044(5) 0.0054(5) C1 0.0269(9) 0.0272(7) 0.0259(7) -0.0010(6) 0.0018(6) 0.0057(7) C2 0.0298(11) 0.0284(8) 0.0612(12) 0.0156(8) 0.0163(8) 0.0107(8) C3 0.0339(11) 0.0469(10) 0.0239(7) 0.0083(7) 0.0055(7) 0.0214(8) C4 0.0210(9) 0.0275(8) 0.0288(8) 0.0070(6) 0.0055(6) 0.0097(6) C5 0.0171(8) 0.0253(7) 0.0137(6) 0.0009(5) 0.0003(5) 0.0023(6) C6 0.0199(8) 0.0204(7) 0.0229(7) -0.0031(5) 0.0019(6) 0.0037(6) C7 0.0164(8) 0.0170(6) 0.0250(7) 0.0017(5) 0.0058(5) 0.0033(5) C8 0.0232(9) 0.0194(7) 0.0367(8) 0.0048(6) 0.0080(6) 0.0032(6) C9 0.0290(10) 0.0213(7) 0.0361(8) 0.0070(6) 0.0077(7) 0.0091(6) C10 0.0247(9) 0.0252(7) 0.0243(7) 0.0067(6) 0.0063(6) 0.0102(6) C11 0.0171(8) 0.0204(7) 0.0178(6) 0.0033(5) 0.0047(5) 0.0061(6) C12 0.0195(8) 0.0202(6) 0.0159(6) 0.0055(5) 0.0033(5) 0.0057(5) C13 0.0195(8) 0.0204(7) 0.0217(7) 0.0002(5) 0.0004(6) 0.0025(6) C14 0.0320(10) 0.0209(7) 0.0262(7) 0.0029(5) 0.0030(6) 0.0051(6) C15 0.0230(9) 0.0209(7) 0.0176(6) -0.0011(5) -0.0009(6) 0.0044(6) C16 0.0347(10) 0.0323(8) 0.0236(7) 0.0076(6) 0.0146(6) 0.0079(7) C17 0.0313(10) 0.0287(8) 0.0178(7) 0.0040(6) 0.0114(6) 0.0026(7) C18 0.0353(10) 0.0276(8) 0.0238(7) -0.0004(6) 0.0045(7) 0.0033(7) C19 0.0477(12) 0.0333(9) 0.0325(8) 0.0047(7) 0.0099(8) 0.0141(8) C20 0.0693(15) 0.0241(8) 0.0330(9) 0.0022(6) 0.0229(9) 0.0050(8) C21 0.0614(14) 0.0346(9) 0.0311(9) -0.0074(7) 0.0116(9) -0.0178(9) C22 0.0383(11) 0.0443(10) 0.0258(8) 0.0034(7) 0.0031(7) -0.0064(8) _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 C5 1.3519(19) . ? O1 C4 1.472(2) . ? O2 C5 1.220(2) . ? O3 C12 1.229(2) . ? O4 C15 1.203(2) . ? O5 C15 1.3375(19) . ? O5 C16 1.462(2) . ? N1 C5 1.339(2) . ? N1 C6 1.455(2) . ? N1 H1 0.880(2) . ? N2 C12 1.344(2) . ? N2 C13 1.461(2) . ? N2 H2 0.880(2) . ? C1 C4 1.526(2) . ? C1 H1B 0.9800 . ? C1 H1A 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.521(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.524(2) . ? C3 H3B 0.9800 . ? C3 H3A 0.9800 . ? C3 H3C 0.9800 . ? C6 C7 1.529(2) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 C8 1.546(2) . ? C7 C11 1.549(2) . ? C7 H7 1.0000 . ? C8 C9 1.525(3) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C9 C10 1.526(2) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 C11 1.554(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.520(2) . ? C11 H11 1.0000 . ? C13 C14 1.526(2) . ? C13 C15 1.533(2) . ? C13 H13 1.0000 . ? C14 H14C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C16 C17 1.499(2) . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? C17 C18 1.387(3) . ? C17 C22 1.389(2) . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.379(3) . ? C19 H19 0.9500 . ? C20 C21 1.367(3) . ? C20 H20 0.9500 . ? C21 C22 1.400(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C5 O1 C4 120.52(13) . . ? C15 O5 C16 115.87(13) . . ? C5 N1 C6 121.51(13) . . ? C5 N1 H1 117.6(14) . . ? C6 N1 H1 118.6(14) . . ? C12 N2 C13 120.03(13) . . ? C12 N2 H2 121.7(12) . . ? C13 N2 H2 117.6(12) . . ? C4 C1 H1B 109.5 . . ? C4 C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? C4 C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3B 109.5 . . ? C4 C3 H3A 109.5 . . ? H3B C3 H3A 109.5 . . ? C4 C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? O1 C4 C2 102.38(14) . . ? O1 C4 C3 109.72(13) . . ? C2 C4 C3 110.42(15) . . ? O1 C4 C1 110.21(13) . . ? C2 C4 C1 109.89(15) . . ? C3 C4 C1 113.64(15) . . ? O2 C5 N1 124.26(14) . . ? O2 C5 O1 125.56(15) . . ? N1 C5 O1 110.16(13) . . ? N1 C6 C7 112.44(11) . . ? N1 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? N1 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? H6B C6 H6A 107.8 . . ? C6 C7 C8 111.68(12) . . ? C6 C7 C11 111.48(12) . . ? C8 C7 C11 105.28(13) . . ? C6 C7 H7 109.4 . . ? C8 C7 H7 109.4 . . ? C11 C7 H7 109.4 . . ? C9 C8 C7 104.68(13) . . ? C9 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? H8B C8 H8A 108.9 . . ? C8 C9 C10 102.70(14) . . ? C8 C9 H9B 111.2 . . ? C10 C9 H9B 111.2 . . ? C8 C9 H9A 111.2 . . ? C10 C9 H9A 111.2 . . ? H9B C9 H9A 109.1 . . ? C9 C10 C11 102.93(13) . . ? C9 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? C9 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? C12 C11 C7 114.05(13) . . ? C12 C11 C10 110.54(12) . . ? C7 C11 C10 105.85(12) . . ? C12 C11 H11 108.8 . . ? C7 C11 H11 108.8 . . ? C10 C11 H11 108.8 . . ? O3 C12 N2 121.81(14) . . ? O3 C12 C11 123.41(13) . . ? N2 C12 C11 114.71(14) . . ? N2 C13 C14 112.43(13) . . ? N2 C13 C15 110.49(12) . . ? C14 C13 C15 111.19(14) . . ? N2 C13 H13 107.5 . . ? C14 C13 H13 107.5 . . ? C15 C13 H13 107.5 . . ? C13 C14 H14C 109.5 . . ? C13 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C15 O5 124.55(14) . . ? O4 C15 C13 124.62(14) . . ? O5 C15 C13 110.76(13) . . ? O5 C16 C17 105.96(14) . . ? O5 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? O5 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? H16B C16 H16A 108.7 . . ? C18 C17 C22 118.49(16) . . ? C18 C17 C16 120.77(15) . . ? C22 C17 C16 120.70(17) . . ? C19 C18 C17 120.91(16) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 C18 120.07(19) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.10(18) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.08(17) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 120.35(19) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? 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 O1 C4 C2 -177.67(13) . . . . ? C5 O1 C4 C3 65.06(17) . . . . ? C5 O1 C4 C1 -60.80(17) . . . . ? C6 N1 C5 O2 10.9(2) . . . . ? C6 N1 C5 O1 -170.49(11) . . . . ? C4 O1 C5 O2 0.2(2) . . . . ? C4 O1 C5 N1 -178.36(11) . . . . ? C5 N1 C6 C7 74.93(17) . . . . ? N1 C6 C7 C8 172.11(13) . . . . ? N1 C6 C7 C11 54.65(17) . . . . ? C6 C7 C8 C9 -99.05(15) . . . . ? C11 C7 C8 C9 22.08(16) . . . . ? C7 C8 C9 C10 -40.22(16) . . . . ? C8 C9 C10 C11 42.26(15) . . . . ? C6 C7 C11 C12 -112.94(14) . . . . ? C8 C7 C11 C12 125.79(13) . . . . ? C6 C7 C11 C10 125.32(13) . . . . ? C8 C7 C11 C10 4.05(15) . . . . ? C9 C10 C11 C12 -152.51(13) . . . . ? C9 C10 C11 C7 -28.54(16) . . . . ? C13 N2 C12 O3 -6.25(19) . . . . ? C13 N2 C12 C11 170.63(12) . . . . ? C7 C11 C12 O3 -13.25(19) . . . . ? C10 C11 C12 O3 105.87(16) . . . . ? C7 C11 C12 N2 169.92(11) . . . . ? C10 C11 C12 N2 -70.96(16) . . . . ? C12 N2 C13 C14 79.69(16) . . . . ? C12 N2 C13 C15 -45.19(17) . . . . ? C16 O5 C15 O4 -9.8(2) . . . . ? C16 O5 C15 C13 173.03(12) . . . . ? N2 C13 C15 O4 142.28(15) . . . . ? C14 C13 C15 O4 16.7(2) . . . . ? N2 C13 C15 O5 -40.53(16) . . . . ? C14 C13 C15 O5 -166.11(12) . . . . ? C15 O5 C16 C17 -169.85(12) . . . . ? O5 C16 C17 C18 -77.86(18) . . . . ? O5 C16 C17 C22 99.59(18) . . . . ? C22 C17 C18 C19 -0.5(2) . . . . ? C16 C17 C18 C19 176.97(16) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C18 C19 C20 C21 0.4(3) . . . . ? C19 C20 C21 C22 -0.1(3) . . . . ? C18 C17 C22 C21 0.8(2) . . . . ? C16 C17 C22 C21 -176.67(16) . . . . ? C20 C21 C22 C17 -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 N1 H1 O2 0.880(2) 2.024(10) 2.835(2) 152.8(19) 1_455 N2 H2 O3 0.880(2) 2.084(3) 2.964(2) 178.7(18) 1_455 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.164 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.035