data_mda55 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O3' _chemical_formula_weight 379.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3877(2) _cell_length_b 8.4043(2) _cell_length_c 15.1821(4) _cell_angle_alpha 100.3570(10) _cell_angle_beta 103.5370(10) _cell_angle_gamma 101.3700(10) _cell_volume 991.00(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4010 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prisms _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7232 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4516 _reflns_number_gt 3470 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0467P)^2^+0.3437P] 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_number_reflns 4516 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.002 _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 N1 N 0.39533(15) 0.42904(15) 0.29172(8) 0.0275(3) Uani 1 1 d . . . C2 C 0.53903(19) 0.49461(18) 0.36411(10) 0.0267(3) Uani 1 1 d . . . C3 C 0.55083(18) 0.36515(17) 0.42127(10) 0.0244(3) Uani 1 1 d . . . C4 C 0.40483(18) 0.22446(17) 0.37418(10) 0.0239(3) Uani 1 1 d . . . C5 C 0.34786(18) 0.07004(18) 0.39068(10) 0.0258(3) Uani 1 1 d . . . H5 H 0.4069 0.0408 0.4444 0.031 Uiso 1 1 calc R . . C6 C 0.20407(18) -0.04299(18) 0.32867(10) 0.0269(3) Uani 1 1 d . . . H6 H 0.1647 -0.1496 0.3397 0.032 Uiso 1 1 calc R . . C7 C 0.11816(18) 0.00192(18) 0.25004(10) 0.0264(3) Uani 1 1 d . . . C8 C 0.17314(18) 0.15831(18) 0.23221(10) 0.0269(3) Uani 1 1 d . . . H8 H 0.1140 0.1886 0.1789 0.032 Uiso 1 1 calc R . . C9 C 0.31568(18) 0.26629(17) 0.29473(10) 0.0247(3) Uani 1 1 d . . . O10 O 0.63698(14) 0.63241(13) 0.37923(8) 0.0335(3) Uani 1 1 d . . . N11 N 0.66705(15) 0.37469(14) 0.49619(8) 0.0247(3) Uani 1 1 d . . . N12 N 0.79440(15) 0.51775(15) 0.52522(9) 0.0255(3) Uani 1 1 d . . . C13 C 0.92455(18) 0.53855(18) 0.60362(10) 0.0256(3) Uani 1 1 d . . . O14 O 0.92947(14) 0.43472(14) 0.65008(8) 0.0378(3) Uani 1 1 d . . . C15 C 1.05916(18) 0.69831(17) 0.62879(10) 0.0251(3) Uani 1 1 d . . . C16 C 1.18317(19) 0.7311(2) 0.71349(10) 0.0316(3) Uani 1 1 d . . . H16 H 1.1804 0.6521 0.7511 0.038 Uiso 1 1 calc R . . C17 C 1.3104(2) 0.8778(2) 0.74318(12) 0.0374(4) Uani 1 1 d . . . H17 H 1.3939 0.8999 0.8012 0.045 Uiso 1 1 calc R . . C18 C 1.3153(2) 0.9923(2) 0.68803(12) 0.0369(4) Uani 1 1 d . . . H18 H 1.4016 1.0936 0.7086 0.044 Uiso 1 1 calc R . . C19 C 1.1953(2) 0.95947(19) 0.60344(12) 0.0347(4) Uani 1 1 d . . . H19 H 1.2001 1.0377 0.5655 0.042 Uiso 1 1 calc R . . C20 C 1.06748(19) 0.81274(18) 0.57334(11) 0.0298(3) Uani 1 1 d . . . H20 H 0.9855 0.7905 0.5147 0.036 Uiso 1 1 calc R . . C21 C 0.3326(2) 0.51718(19) 0.22185(10) 0.0299(3) Uani 1 1 d . . . H21A H 0.3713 0.6390 0.2494 0.036 Uiso 1 1 calc R . . H21B H 0.2072 0.4861 0.2035 0.036 Uiso 1 1 calc R . . C22 C 0.3933(2) 0.4769(2) 0.13540(12) 0.0398(4) Uani 1 1 d . . . H22A H 0.3753 0.3543 0.1155 0.048 Uiso 1 1 calc R . . H22B H 0.5165 0.5279 0.1515 0.048 Uiso 1 1 calc R . . C23 C 0.3024(3) 0.5399(2) 0.05409(12) 0.0492(5) Uani 1 1 d . . . H23A H 0.3435 0.5036 -0.0004 0.059 Uiso 1 1 calc R . . H23B H 0.1798 0.4857 0.0372 0.059 Uiso 1 1 calc R . . C24 C 0.3251(2) 0.7262(2) 0.07223(12) 0.0449(4) Uani 1 1 d . . . H24A H 0.4477 0.7818 0.0926 0.054 Uiso 1 1 calc R . . H24B H 0.2765 0.7626 0.1236 0.054 Uiso 1 1 calc R . . C25 C 0.2405(3) 0.7817(3) -0.01384(14) 0.0582(6) Uani 1 1 d . . . H25A H 0.2924 0.7492 -0.0644 0.070 Uiso 1 1 calc R . . H25B H 0.1189 0.7224 -0.0357 0.070 Uiso 1 1 calc R . . C26 C 0.2567(3) 0.9670(3) 0.00473(15) 0.0645(6) Uani 1 1 d . . . H26A H 0.2011 0.9993 0.0527 0.097 Uiso 1 1 calc R . . H26B H 0.2027 0.9958 -0.0528 0.097 Uiso 1 1 calc R . . H26C H 0.3768 1.0265 0.0264 0.097 Uiso 1 1 calc R . . O27 O -0.02327(13) -0.09873(13) 0.18462(7) 0.0345(3) Uani 1 1 d . . . C28 C -0.0940(2) -0.25638(19) 0.20073(12) 0.0378(4) Uani 1 1 d . . . H28A H -0.0128 -0.3257 0.2010 0.057 Uiso 1 1 calc R . . H28B H -0.1987 -0.3127 0.1511 0.057 Uiso 1 1 calc R . . H28C H -0.1191 -0.2388 0.2611 0.057 Uiso 1 1 calc R . . H12N H 0.787(2) 0.596(2) 0.4927(11) 0.028(4) Uiso 1 1 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 N1 0.0304(7) 0.0232(6) 0.0301(7) 0.0124(5) 0.0070(5) 0.0053(5) C2 0.0294(8) 0.0230(8) 0.0295(8) 0.0082(6) 0.0102(6) 0.0062(6) C3 0.0269(7) 0.0222(7) 0.0267(7) 0.0077(6) 0.0098(6) 0.0071(6) C4 0.0248(7) 0.0229(7) 0.0256(7) 0.0079(6) 0.0075(6) 0.0067(6) C5 0.0255(7) 0.0262(8) 0.0275(7) 0.0118(6) 0.0053(6) 0.0080(6) C6 0.0276(8) 0.0226(7) 0.0316(8) 0.0107(6) 0.0075(6) 0.0057(6) C7 0.0244(7) 0.0257(8) 0.0282(8) 0.0066(6) 0.0062(6) 0.0050(6) C8 0.0283(8) 0.0287(8) 0.0259(7) 0.0123(6) 0.0057(6) 0.0091(6) C9 0.0275(8) 0.0221(7) 0.0282(7) 0.0097(6) 0.0107(6) 0.0078(6) O10 0.0366(6) 0.0227(6) 0.0388(6) 0.0119(5) 0.0079(5) 0.0008(5) N11 0.0244(6) 0.0207(6) 0.0280(6) 0.0055(5) 0.0074(5) 0.0035(5) N12 0.0287(7) 0.0195(6) 0.0266(6) 0.0070(5) 0.0056(5) 0.0029(5) C13 0.0291(8) 0.0231(7) 0.0253(7) 0.0072(6) 0.0082(6) 0.0059(6) O14 0.0400(6) 0.0299(6) 0.0375(6) 0.0168(5) 0.0005(5) -0.0001(5) C15 0.0268(7) 0.0217(7) 0.0275(8) 0.0047(6) 0.0095(6) 0.0060(6) C16 0.0342(8) 0.0311(8) 0.0271(8) 0.0075(6) 0.0075(6) 0.0034(7) C17 0.0339(9) 0.0379(9) 0.0312(8) 0.0009(7) 0.0042(7) 0.0006(7) C18 0.0325(9) 0.0239(8) 0.0475(10) -0.0006(7) 0.0128(7) -0.0018(6) C19 0.0371(9) 0.0248(8) 0.0459(10) 0.0135(7) 0.0154(7) 0.0070(7) C20 0.0309(8) 0.0248(8) 0.0341(8) 0.0092(6) 0.0081(6) 0.0070(6) C21 0.0340(8) 0.0274(8) 0.0314(8) 0.0154(6) 0.0083(6) 0.0081(6) C22 0.0498(10) 0.0381(9) 0.0371(9) 0.0159(7) 0.0174(8) 0.0113(8) C23 0.0619(12) 0.0503(12) 0.0300(9) 0.0123(8) 0.0110(8) 0.0014(9) C24 0.0527(11) 0.0485(11) 0.0321(9) 0.0157(8) 0.0086(8) 0.0082(9) C25 0.0617(13) 0.0677(14) 0.0420(11) 0.0312(10) 0.0024(9) 0.0068(11) C26 0.0822(16) 0.0768(16) 0.0480(12) 0.0332(11) 0.0152(11) 0.0371(13) O27 0.0321(6) 0.0288(6) 0.0340(6) 0.0110(5) -0.0024(5) -0.0014(5) C28 0.0360(9) 0.0271(9) 0.0408(9) 0.0084(7) 0.0005(7) -0.0013(7) _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 N1 C2 1.3655(19) . ? N1 C9 1.4128(18) . ? N1 C21 1.4581(18) . ? C2 O10 1.2287(17) . ? C2 C3 1.513(2) . ? C3 N11 1.2913(19) . ? C3 C4 1.457(2) . ? C4 C5 1.380(2) . ? C4 C9 1.404(2) . ? C5 C6 1.392(2) . ? C5 H5 0.9500 . ? C6 C7 1.398(2) . ? C6 H6 0.9500 . ? C7 O27 1.3638(17) . ? C7 C8 1.400(2) . ? C8 C9 1.373(2) . ? C8 H8 0.9500 . ? N11 N12 1.3651(17) . ? N12 C13 1.3714(19) . ? N12 H12N 0.894(17) . ? C13 O14 1.2175(17) . ? C13 C15 1.496(2) . ? C15 C20 1.389(2) . ? C15 C16 1.395(2) . ? C16 C17 1.385(2) . ? C16 H16 0.9500 . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 C19 1.377(2) . ? C18 H18 0.9500 . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.523(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.529(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.506(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.531(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.505(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O27 C28 1.4290(19) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 N1 C9 110.84(12) . . ? C2 N1 C21 124.15(12) . . ? C9 N1 C21 125.00(12) . . ? O10 C2 N1 126.10(13) . . ? O10 C2 C3 127.59(14) . . ? N1 C2 C3 106.31(12) . . ? N11 C3 C4 126.28(13) . . ? N11 C3 C2 127.51(13) . . ? C4 C3 C2 106.20(12) . . ? C5 C4 C9 119.28(13) . . ? C5 C4 C3 133.89(13) . . ? C9 C4 C3 106.78(12) . . ? C4 C5 C6 120.12(13) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 119.33(13) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? O27 C7 C6 124.38(13) . . ? O27 C7 C8 114.11(13) . . ? C6 C7 C8 121.52(13) . . ? C9 C8 C7 117.51(13) . . ? C9 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C8 C9 C4 122.24(13) . . ? C8 C9 N1 127.96(13) . . ? C4 C9 N1 109.80(12) . . ? C3 N11 N12 115.32(12) . . ? N11 N12 C13 119.58(12) . . ? N11 N12 H12N 117.7(10) . . ? C13 N12 H12N 122.7(11) . . ? O14 C13 N12 122.25(14) . . ? O14 C13 C15 122.27(13) . . ? N12 C13 C15 115.48(13) . . ? C20 C15 C16 119.12(14) . . ? C20 C15 C13 124.22(13) . . ? C16 C15 C13 116.67(13) . . ? C17 C16 C15 120.48(15) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.79(15) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 120.12(15) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.36(15) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C15 120.11(15) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? N1 C21 C22 112.19(13) . . ? N1 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? N1 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C21 C22 C23 113.03(15) . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C22 115.31(15) . . ? C24 C23 H23A 108.4 . . ? C22 C23 H23A 108.4 . . ? C24 C23 H23B 108.4 . . ? C22 C23 H23B 108.4 . . ? H23A C23 H23B 107.5 . . ? C23 C24 C25 112.59(16) . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? C25 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 112.93(17) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C7 O27 C28 117.62(12) . . ? O27 C28 H28A 109.5 . . ? O27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C9 N1 C2 O10 178.59(14) . . . . ? C21 N1 C2 O10 -2.2(2) . . . . ? C9 N1 C2 C3 -2.05(15) . . . . ? C21 N1 C2 C3 177.19(12) . . . . ? O10 C2 C3 N11 -0.7(2) . . . . ? N1 C2 C3 N11 179.92(14) . . . . ? O10 C2 C3 C4 -179.99(14) . . . . ? N1 C2 C3 C4 0.66(15) . . . . ? N11 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C5 178.43(15) . . . . ? N11 C3 C4 C9 -178.32(13) . . . . ? C2 C3 C4 C9 0.94(15) . . . . ? C9 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C6 -176.84(15) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C5 C6 C7 O27 179.74(13) . . . . ? C5 C6 C7 C8 -0.1(2) . . . . ? O27 C7 C8 C9 -179.56(12) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C4 -0.2(2) . . . . ? C7 C8 C9 N1 179.75(14) . . . . ? C5 C4 C9 C8 -0.2(2) . . . . ? C3 C4 C9 C8 177.72(13) . . . . ? C5 C4 C9 N1 179.87(12) . . . . ? C3 C4 C9 N1 -2.21(16) . . . . ? C2 N1 C9 C8 -177.16(14) . . . . ? C21 N1 C9 C8 3.6(2) . . . . ? C2 N1 C9 C4 2.76(16) . . . . ? C21 N1 C9 C4 -176.47(13) . . . . ? C4 C3 N11 N12 177.91(12) . . . . ? C2 C3 N11 N12 -1.2(2) . . . . ? C3 N11 N12 C13 -179.33(12) . . . . ? N11 N12 C13 O14 -1.5(2) . . . . ? N11 N12 C13 C15 179.09(11) . . . . ? O14 C13 C15 C20 173.55(14) . . . . ? N12 C13 C15 C20 -7.1(2) . . . . ? O14 C13 C15 C16 -6.1(2) . . . . ? N12 C13 C15 C16 173.24(13) . . . . ? C20 C15 C16 C17 1.8(2) . . . . ? C13 C15 C16 C17 -178.56(14) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C16 C17 C18 C19 -0.7(2) . . . . ? C17 C18 C19 C20 0.8(2) . . . . ? C18 C19 C20 C15 0.4(2) . . . . ? C16 C15 C20 C19 -1.7(2) . . . . ? C13 C15 C20 C19 178.65(14) . . . . ? C2 N1 C21 C22 94.06(17) . . . . ? C9 N1 C21 C22 -86.81(17) . . . . ? N1 C21 C22 C23 168.75(14) . . . . ? C21 C22 C23 C24 61.5(2) . . . . ? C22 C23 C24 C25 176.30(16) . . . . ? C23 C24 C25 C26 177.72(18) . . . . ? C6 C7 O27 C28 4.1(2) . . . . ? C8 C7 O27 C28 -176.05(13) . . . . ? 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 N12 H12N O10 0.894(17) 1.992(17) 2.7357(16) 139.7(14) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.390 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.041