data_cook101 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H0 N2 O' _chemical_formula_weight 212.16 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 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' '-x, -y, z' _cell_length_a 14.2022(11) _cell_length_b 14.2864(9) _cell_length_c 11.7464(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2383.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2363 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.41 _exptl_crystal_description 'rod' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.042 _exptl_crystal_size_mid 0.082 _exptl_crystal_size_max 0.313 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.078 ############################################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # # # ############################################################################## _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000c)' _exptl_absorpt_correction_T_min 0.9760 _exptl_absorpt_correction_T_max 0.9967 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) # SMART APEX II parameters _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II 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 25345 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.48 _reflns_number_total 5989 _reflns_number_gt 4301 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001)' _computing_data_reduction ; Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _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^)+(0.0572P)^2^+0.1532P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.0(14) _refine_ls_number_reflns 5989 _refine_ls_number_parameters 304 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C 0.60555(16) 0.62316(16) 0.53033(17) 0.0220(5) Uani 1 1 d . . . C2 C 0.62939(16) 0.61193(16) 0.41510(18) 0.0244(5) Uani 1 1 d . . . H2A H 0.6936 0.6075 0.3931 0.029 Uiso 1 1 calc R . . C3 C 0.55987(17) 0.60737(16) 0.33463(18) 0.0257(5) Uani 1 1 d . . . H3A H 0.5742 0.5998 0.2562 0.031 Uiso 1 1 calc R . . C4 C 0.46819(16) 0.61422(15) 0.37229(17) 0.0216(5) Uani 1 1 d . . . N5 N 0.38420(13) 0.61125(13) 0.31421(15) 0.0235(4) Uani 1 1 d . . . H5A H 0.3778 0.6060 0.2400 0.028 Uiso 1 1 calc R . . C6 C 0.31164(16) 0.61797(16) 0.39165(17) 0.0232(5) Uani 1 1 d . . . C7 C 0.21534(17) 0.61593(17) 0.37214(19) 0.0266(5) Uani 1 1 d . . . H7A H 0.1908 0.6070 0.2977 0.032 Uiso 1 1 calc R . . C8 C 0.15616(17) 0.62737(17) 0.46498(18) 0.0289(5) Uani 1 1 d . . . H8A H 0.0899 0.6266 0.4540 0.035 Uiso 1 1 calc R . . C9 C 0.19278(17) 0.64014(16) 0.57517(19) 0.0272(5) Uani 1 1 d . . . H9A H 0.1508 0.6488 0.6373 0.033 Uiso 1 1 calc R . . C10 C 0.28826(16) 0.64034(15) 0.59442(18) 0.0233(5) Uani 1 1 d . . . H10A H 0.3123 0.6478 0.6693 0.028 Uiso 1 1 calc R . . C11 C 0.34932(15) 0.62933(15) 0.50227(16) 0.0203(4) Uani 1 1 d U . . C12 C 0.44984(16) 0.62543(16) 0.48942(17) 0.0221(5) Uani 1 1 d . . . N13 N 0.51839(13) 0.63008(13) 0.56881(14) 0.0212(4) Uani 1 1 d . . . O14 O 0.67154(10) 0.62673(11) 0.61523(12) 0.0234(3) Uani 1 1 d . . . C15 C 0.76849(14) 0.62338(17) 0.58038(18) 0.0236(5) Uani 1 1 d . . . H15A H 0.7836 0.6787 0.5330 0.028 Uiso 1 1 calc R . . H15B H 0.7801 0.5663 0.5346 0.028 Uiso 1 1 calc R . . C16 C 0.82958(16) 0.62251(18) 0.68511(18) 0.0274(5) Uani 1 1 d . . . H16A H 0.8165 0.5656 0.7306 0.033 Uiso 1 1 calc R . . H16B H 0.8156 0.6780 0.7328 0.033 Uiso 1 1 calc R . . C17 C 0.93441(10) 0.62383(12) 0.64844(17) 0.0334(6) Uani 1 1 d . . . H17A H 0.9746 0.6245 0.7163 0.050 Uiso 1 1 calc R . . H17B H 0.9467 0.6799 0.6028 0.050 Uiso 1 1 calc R . . H17C H 0.9482 0.5679 0.6031 0.050 Uiso 1 1 calc R . . C1' C 0.32093(10) 0.49620(12) 1.03461(11) 0.0230(5) Uani 1 1 d R . . C2' C 0.31817(10) 0.46935(10) 0.92119(13) 0.0254(5) Uani 1 1 d R . . H2'A H 0.2803 0.4174 0.8999 0.030 Uiso 1 1 calc R . . C3' C 0.36842(17) 0.51552(15) 0.83877(18) 0.0247(5) Uani 1 1 d . . . H3'A H 0.3651 0.4975 0.7610 0.030 Uiso 1 1 calc R . . C4' C 0.42371(16) 0.58893(15) 0.87380(18) 0.0213(5) Uani 1 1 d . . . N5' N 0.48398(13) 0.64613(12) 0.81446(15) 0.0234(4) Uani 1 1 d . . . H5'A H 0.4946 0.6437 0.7407 0.028 Uiso 1 1 calc R . . C6' C 0.52493(16) 0.70769(15) 0.88922(18) 0.0238(5) Uani 1 1 d . . . C7' C 0.59252(18) 0.77504(18) 0.8684(2) 0.0343(6) Uani 1 1 d . . . H7'A H 0.6184 0.7831 0.7944 0.041 Uiso 1 1 calc R . . C8' C 0.6213(2) 0.83022(19) 0.9580(2) 0.0398(7) Uani 1 1 d . . . H8'A H 0.6669 0.8777 0.9451 0.048 Uiso 1 1 calc R . . C9' C 0.58490(19) 0.81776(18) 1.0675(2) 0.0370(6) Uani 1 1 d . . . H9'A H 0.6059 0.8570 1.1277 0.044 Uiso 1 1 calc R . . C10' C 0.51886(18) 0.74935(16) 1.08950(18) 0.0278(5) Uani 1 1 d . . . H10B H 0.4942 0.7412 1.1640 0.033 Uiso 1 1 calc R . . C11' C 0.48892(16) 0.69216(15) 0.99993(17) 0.0220(5) Uani 1 1 d U . . C12' C 0.42482(15) 0.61504(16) 0.98972(17) 0.0208(5) Uani 1 1 d . . . N13' N 0.37469(13) 0.56907(13) 1.07047(14) 0.0211(4) Uani 1 1 d . . . O14' O 0.27619(12) 0.45337(11) 1.12048(12) 0.0271(4) Uani 1 1 d . . . C15' C 0.22340(18) 0.37076(17) 1.08929(18) 0.0314(6) Uani 1 1 d . . . H15C H 0.2637 0.3280 1.0444 0.038 Uiso 1 1 calc R . . H15D H 0.1686 0.3886 1.0419 0.038 Uiso 1 1 calc R . . C16' C 0.1904(2) 0.32265(19) 1.1948(2) 0.0383(7) Uani 1 1 d . . . H16C H 0.2459 0.3078 1.2425 0.046 Uiso 1 1 calc R . . H16D H 0.1605 0.2627 1.1730 0.046 Uiso 1 1 calc R . . C17' C 0.1210(2) 0.3786(2) 1.2659(2) 0.0492(7) Uani 1 1 d . . . H17D H 0.0992 0.3404 1.3300 0.074 Uiso 1 1 calc R . . H17E H 0.0670 0.3965 1.2187 0.074 Uiso 1 1 calc R . . H17F H 0.1519 0.4351 1.2950 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0282(13) 0.0181(10) 0.0198(11) -0.0007(9) 0.0005(9) 0.0007(10) C2 0.0259(12) 0.0247(11) 0.0224(11) -0.0001(9) 0.0062(9) 0.0015(10) C3 0.0337(14) 0.0237(12) 0.0195(11) 0.0011(9) 0.0058(9) 0.0021(10) C4 0.0267(12) 0.0190(10) 0.0191(10) 0.0010(9) 0.0011(9) 0.0008(10) N5 0.0284(11) 0.0265(10) 0.0155(8) 0.0009(7) -0.0019(7) 0.0035(9) C6 0.0287(13) 0.0191(11) 0.0217(11) 0.0011(9) -0.0009(9) 0.0025(10) C7 0.0299(14) 0.0258(12) 0.0242(11) 0.0015(10) -0.0057(10) 0.0016(11) C8 0.0259(13) 0.0287(13) 0.0320(12) 0.0013(10) -0.0040(10) 0.0044(11) C9 0.0275(13) 0.0272(13) 0.0268(12) -0.0009(10) 0.0022(10) 0.0053(10) C10 0.0277(13) 0.0237(12) 0.0186(11) 0.0004(9) -0.0006(9) 0.0028(10) C11 0.0224(10) 0.0175(9) 0.0211(9) 0.0027(8) -0.0012(8) 0.0012(9) C12 0.0273(12) 0.0192(11) 0.0199(10) 0.0022(9) -0.0005(9) 0.0019(10) N13 0.0238(10) 0.0211(9) 0.0186(8) 0.0008(7) 0.0024(7) -0.0019(8) O14 0.0196(8) 0.0306(8) 0.0200(7) 0.0005(7) 0.0012(6) -0.0020(7) C15 0.0194(11) 0.0250(11) 0.0262(11) 0.0006(10) 0.0055(9) -0.0023(10) C16 0.0263(13) 0.0302(12) 0.0258(11) -0.0022(10) 0.0020(10) -0.0016(11) C17 0.0255(14) 0.0368(14) 0.0380(14) -0.0024(12) -0.0004(10) 0.0021(12) C1' 0.0272(14) 0.0213(11) 0.0205(11) 0.0033(8) -0.0040(9) -0.0017(10) C2' 0.0295(13) 0.0233(12) 0.0233(11) -0.0027(9) -0.0072(10) 0.0001(10) C3' 0.0309(14) 0.0245(12) 0.0187(10) -0.0027(9) -0.0032(9) 0.0040(10) C4' 0.0230(12) 0.0218(11) 0.0190(10) 0.0009(8) 0.0010(9) 0.0053(9) N5' 0.0265(11) 0.0272(10) 0.0165(8) 0.0019(7) 0.0024(8) 0.0029(8) C6' 0.0250(13) 0.0274(12) 0.0190(10) 0.0044(9) -0.0006(9) 0.0011(10) C7' 0.0335(15) 0.0395(14) 0.0300(13) 0.0083(11) 0.0037(11) -0.0081(12) C8' 0.0437(17) 0.0389(15) 0.0368(15) 0.0085(11) 0.0019(12) -0.0183(13) C9' 0.0464(17) 0.0369(15) 0.0278(13) 0.0003(11) -0.0022(12) -0.0158(13) C10' 0.0338(14) 0.0291(12) 0.0206(11) 0.0009(9) 0.0003(10) -0.0035(11) C11' 0.0227(11) 0.0232(10) 0.0200(9) 0.0004(8) 0.0005(9) -0.0007(9) C12' 0.0208(12) 0.0233(11) 0.0183(10) -0.0007(9) 0.0019(8) 0.0030(10) N13' 0.0239(10) 0.0212(9) 0.0182(9) 0.0002(7) 0.0001(8) -0.0015(8) O14' 0.0336(10) 0.0278(9) 0.0198(8) 0.0033(6) -0.0027(7) -0.0119(7) C15' 0.0372(14) 0.0277(13) 0.0292(12) 0.0040(10) -0.0114(11) -0.0153(12) C16' 0.0443(17) 0.0395(15) 0.0310(13) 0.0068(11) -0.0107(12) -0.0208(13) C17' 0.0489(18) 0.0570(18) 0.0417(15) 0.0025(15) 0.0020(13) -0.0216(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 C1 N13 1.322(3) . ? C1 O14 1.369(3) . ? C1 C2 1.404(3) . ? C2 C3 1.369(3) . ? C2 H2A 0.9500 . ? C3 C4 1.379(3) . ? C3 H3A 0.9500 . ? C4 N5 1.375(3) . ? C4 C12 1.409(3) . ? N5 C6 1.378(3) . ? N5 H5A 0.8800 . ? C6 C7 1.387(3) . ? C6 C11 1.415(3) . ? C7 C8 1.386(3) . ? C7 H7A 0.9500 . ? C8 C9 1.407(3) . ? C8 H8A 0.9500 . ? C9 C10 1.375(3) . ? C9 H9A 0.9500 . ? C10 C11 1.396(3) . ? C10 H10A 0.9500 . ? C11 C12 1.437(3) . ? C12 N13 1.350(3) . ? O14 C15 1.437(2) . ? C15 C16 1.505(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.550(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C1' O14' 1.3400(19) . ? C1' N13' 1.358(2) . ? C1' C2' 1.3869 . ? C2' C3' 1.372(3) . ? C2' H2'A 0.9500 . ? C3' C4' 1.373(3) . ? C3' H3'A 0.9500 . ? C4' N5' 1.373(3) . ? C4' C12' 1.412(3) . ? N5' C6' 1.372(3) . ? N5' H5'A 0.8800 . ? C6' C7' 1.381(3) . ? C6' C11' 1.415(3) . ? C7' C8' 1.377(4) . ? C7' H7'A 0.9500 . ? C8' C9' 1.398(3) . ? C8' H8'A 0.9500 . ? C9' C10' 1.379(3) . ? C9' H9'A 0.9500 . ? C10' C11' 1.398(3) . ? C10' H10B 0.9500 . ? C11' C12' 1.434(3) . ? C12' N13' 1.356(3) . ? O14' C15' 1.445(3) . ? C15' C16' 1.493(3) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C17' 1.520(4) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 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 N13 C1 O14 112.90(17) . . ? N13 C1 C2 124.3(2) . . ? O14 C1 C2 122.8(2) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 117.2(2) . . ? C2 C3 H3A 121.4 . . ? C4 C3 H3A 121.4 . . ? N5 C4 C3 131.15(19) . . ? N5 C4 C12 109.11(19) . . ? C3 C4 C12 119.7(2) . . ? C4 N5 C6 108.62(17) . . ? C4 N5 H5A 125.7 . . ? C6 N5 H5A 125.7 . . ? N5 C6 C7 128.8(2) . . ? N5 C6 C11 109.36(19) . . ? C7 C6 C11 121.8(2) . . ? C8 C7 C6 117.7(2) . . ? C8 C7 H7A 121.1 . . ? C6 C7 H7A 121.1 . . ? C7 C8 C9 121.0(2) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C11 119.0(2) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? C10 C11 C6 119.4(2) . . ? C10 C11 C12 134.7(2) . . ? C6 C11 C12 105.96(18) . . ? N13 C12 C4 123.1(2) . . ? N13 C12 C11 129.96(19) . . ? C4 C12 C11 106.90(19) . . ? C1 N13 C12 115.82(18) . . ? C1 O14 C15 116.55(16) . . ? O14 C15 C16 108.65(17) . . ? O14 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O14 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.3 . . ? C15 C16 C17 109.05(17) . . ? C15 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? C15 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O14' C1' N13' 112.53(14) . . ? O14' C1' C2' 125.69(11) . . ? N13' C1' C2' 121.73(10) . . ? C3' C2' C1' 122.03(11) . . ? C3' C2' H2'A 119.0 . . ? C1' C2' H2'A 119.0 . . ? C2' C3' C4' 116.95(19) . . ? C2' C3' H3'A 121.5 . . ? C4' C3' H3'A 121.5 . . ? C3' C4' N5' 131.2(2) . . ? C3' C4' C12' 119.8(2) . . ? N5' C4' C12' 108.99(19) . . ? C6' N5' C4' 108.70(18) . . ? C6' N5' H5'A 125.6 . . ? C4' N5' H5'A 125.6 . . ? N5' C6' C7' 128.9(2) . . ? N5' C6' C11' 109.54(19) . . ? C7' C6' C11' 121.6(2) . . ? C8' C7' C6' 118.0(2) . . ? C8' C7' H7'A 121.0 . . ? C6' C7' H7'A 121.0 . . ? C7' C8' C9' 121.4(2) . . ? C7' C8' H8'A 119.3 . . ? C9' C8' H8'A 119.3 . . ? C10' C9' C8' 121.0(2) . . ? C10' C9' H9'A 119.5 . . ? C8' C9' H9'A 119.5 . . ? C9' C10' C11' 118.7(2) . . ? C9' C10' H10B 120.7 . . ? C11' C10' H10B 120.7 . . ? C10' C11' C6' 119.3(2) . . ? C10' C11' C12' 134.8(2) . . ? C6' C11' C12' 105.85(18) . . ? N13' C12' C4' 122.7(2) . . ? N13' C12' C11' 130.32(19) . . ? C4' C12' C11' 106.90(18) . . ? C12' N13' C1' 116.72(16) . . ? C1' O14' C15' 115.34(15) . . ? O14' C15' C16' 109.16(18) . . ? O14' C15' H15C 109.8 . . ? C16' C15' H15C 109.8 . . ? O14' C15' H15D 109.8 . . ? C16' C15' H15D 109.8 . . ? H15C C15' H15D 108.3 . . ? C15' C16' C17' 114.7(2) . . ? C15' C16' H16C 108.6 . . ? C17' C16' H16C 108.6 . . ? C15' C16' H16D 108.6 . . ? C17' C16' H16D 108.6 . . ? H16C C16' H16D 107.6 . . ? C16' C17' H17D 109.5 . . ? C16' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? C16' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 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 N13 C1 C2 C3 -0.1(4) . . . . ? O14 C1 C2 C3 178.9(2) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 N5 -179.3(2) . . . . ? C2 C3 C4 C12 0.0(3) . . . . ? C3 C4 N5 C6 177.9(2) . . . . ? C12 C4 N5 C6 -1.5(2) . . . . ? C4 N5 C6 C7 -178.4(2) . . . . ? C4 N5 C6 C11 2.4(2) . . . . ? N5 C6 C7 C8 -177.8(2) . . . . ? C11 C6 C7 C8 1.3(4) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? C9 C10 C11 C12 -179.5(2) . . . . ? N5 C6 C11 C10 178.2(2) . . . . ? C7 C6 C11 C10 -1.1(3) . . . . ? N5 C6 C11 C12 -2.3(3) . . . . ? C7 C6 C11 C12 178.5(2) . . . . ? N5 C4 C12 N13 179.5(2) . . . . ? C3 C4 C12 N13 0.1(4) . . . . ? N5 C4 C12 C11 0.0(3) . . . . ? C3 C4 C12 C11 -179.4(2) . . . . ? C10 C11 C12 N13 1.3(5) . . . . ? C6 C11 C12 N13 -178.1(2) . . . . ? C10 C11 C12 C4 -179.3(2) . . . . ? C6 C11 C12 C4 1.4(3) . . . . ? O14 C1 N13 C12 -178.92(19) . . . . ? C2 C1 N13 C12 0.2(3) . . . . ? C4 C12 N13 C1 -0.2(3) . . . . ? C11 C12 N13 C1 179.1(2) . . . . ? N13 C1 O14 C15 -177.65(19) . . . . ? C2 C1 O14 C15 3.2(3) . . . . ? C1 O14 C15 C16 -176.81(18) . . . . ? O14 C15 C16 C17 -177.24(18) . . . . ? O14' C1' C2' C3' -178.0(2) . . . . ? N13' C1' C2' C3' -0.92(18) . . . . ? C1' C2' C3' C4' 1.4(3) . . . . ? C2' C3' C4' N5' 177.4(2) . . . . ? C2' C3' C4' C12' -1.6(3) . . . . ? C3' C4' N5' C6' -178.3(2) . . . . ? C12' C4' N5' C6' 0.8(2) . . . . ? C4' N5' C6' C7' 177.1(2) . . . . ? C4' N5' C6' C11' -1.5(3) . . . . ? N5' C6' C7' C8' 178.6(2) . . . . ? C11' C6' C7' C8' -2.9(4) . . . . ? C6' C7' C8' C9' 1.2(4) . . . . ? C7' C8' C9' C10' 0.2(4) . . . . ? C8' C9' C10' C11' 0.1(4) . . . . ? C9' C10' C11' C6' -1.8(3) . . . . ? C9' C10' C11' C12' 178.7(3) . . . . ? N5' C6' C11' C10' -178.0(2) . . . . ? C7' C6' C11' C10' 3.2(3) . . . . ? N5' C6' C11' C12' 1.6(3) . . . . ? C7' C6' C11' C12' -177.1(2) . . . . ? C3' C4' C12' N13' 1.6(3) . . . . ? N5' C4' C12' N13' -177.6(2) . . . . ? C3' C4' C12' C11' 179.4(2) . . . . ? N5' C4' C12' C11' 0.2(2) . . . . ? C10' C11' C12' N13' -3.9(4) . . . . ? C6' C11' C12' N13' 176.5(2) . . . . ? C10' C11' C12' C4' 178.4(3) . . . . ? C6' C11' C12' C4' -1.1(2) . . . . ? C4' C12' N13' C1' -1.0(3) . . . . ? C11' C12' N13' C1' -178.4(2) . . . . ? O14' C1' N13' C12' 178.16(17) . . . . ? C2' C1' N13' C12' 0.7(2) . . . . ? N13' C1' O14' C15' -175.48(17) . . . . ? C2' C1' O14' C15' 1.9(2) . . . . ? C1' O14' C15' C16' 171.2(2) . . . . ? O14' C15' C16' C17' 64.5(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 N5 H5A N13' 0.88 2.06 2.929(2) 169.1 1_554 N5' H5'A N13 0.88 2.06 2.935(2) 176.8 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.349 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.068