# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/181 data_global # 1. SUBMISSION DETAILS _publ_contact_autor ; 'Kirfel, Armin' Mineralogisch-Petrologisches Institut Universit\"at Bonn Poppelsdorfer Schloss D-53115 Bonn ; _publ_contact_author_phone '0049 228 73-2760' _publ_contact_author_fax '0049 228 73-2770' _publ_contact_author_email 'kirfel@uni-bonn.de' _publ_requested_journal 'Journal of Chemical Society, Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis, X-ray analysis and Spectroscopic Characterization of the Hemiaminal Cyclization Product from 2,4-dipyridine substituted 3,7-Diazabicyclo[3.3.1] nonanone 1,5-diesters ; loop_ _publ_author_name _publ_author_address 'Kuhl, Ulrich' ; Institut fuer Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; 'Cambareri, Antonella' ; Institut fuer Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; 'Sauber, Christian' ; Institut f\"ur Biomedizinische und Pharmazeutische Forschung, IBMP Schleifweg 3 D-90562 Nrnberg-Heroldsberg ; 'S\"orgel, Fritz' ; Institut f\"ur Biomedizinische und Pharmazeutische Forschung, IBMP Schleifweg 3 D-90562 Nrnberg-Heroldsberg ; 'Hartmann, Rudolf' ; Institut f\"ur Biomedizinische und Pharmazeutische Forschung, IBMP Schleifweg 3 D-90562 Nrnberg-Heroldsberg ; 'Euler, Harald' ; Mineralogisch-Petrologisches Institut Universit\"at Bonn Poppelsdorfer Schloss D-53115 Bonn ; 'Kirfel, Armin' ; Mineralogisch-Petrologisches Institut Universit\"at Bonn Poppelsdorfer Schloss D-53115 Bonn ; 'Holzgrabe, Ulrike' ; Institut f\"ur Physiologische Chemie Universit\"at Bonn Nussallee 11 D-53115 Bonn, FRG ; #============================================================================== # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; The 2,4-dipyridine substituted 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9- one-1,5-diester, HZ2, was found to exhibit high affinity and selectivity to kappa-opioid receptor. Thus, the compound attracts interest as an opioid-like analgesic which can be used for the treatment of strong pain caused by tumors or operations (see ref. 1). ; _publ_section_experimental ; The 2,4-dipyridine substituted 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9- one-1,5-diester, HZ2, was achieved by a double Mannich reaction, using, in the first step, oxoglutaric acid, methylamine and pyridine aldehyde and, in the second step, the previously obtained piperidone, formaldehyde and methylamine (see ref. 2). The conversion of HZ2 into a perchloric salt was performed in EtOH by adding a more than tenfold surplus of the corresponding acid to the HZ2 solution. From the reaction solution, crystals with properties different from the expected salt were isolated. ; _publ_section_references ; Holzgrabe U., Nachtsheim C., Siener T., Drosihn S. and Brandt W., Pharmazie 52, 1997, 4 - 22 Samhammer A., Holzgrabe U. and Haller R., Arch. Pharm. (Weinheim) 322, 1989, 551 - 555 ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== data_holz-1 _audit_creation_method SHELXL _chemical_name_systematic ; (+-)-4a-Hydroxy-4,10a-bis(methoxycarbonyl)-2,11-dimethyl-12syn-(2-pyridyl)- 2,3,4,4at,10,10at-hexahydro-10c,4r-(iminomethano)-1H-pyrido[3,4-b]indolizinium perchlorate monohydroperchlorate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H28 Cl2 N4 O14' _chemical_formula_weight 655.39 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P212121 (No. 19)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 15.127(9) _cell_length_b 17.123(5) _cell_length_c 11.304(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2928(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 5.25 _cell_measurement_theta_max 8.19 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method ? _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.90 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC-6R' _diffrn_measurement_method 'Omega-scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3157 _diffrn_reflns_av_R_equivalents 0.1307 _diffrn_reflns_av_sigmaI/netI 0.3408 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 19.99 _reflns_number_total 2727 _reflns_number_observed 1279 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC TEXSAN v5.0' _computing_cell_refinement 'MSC TEXSAN v5.0' _computing_data_reduction 'REDUCE (Eichhorn, 1987)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'DIAMOND (Bergerhoff, 1995)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+11.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _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 -0.16(28) _refine_ls_number_reflns 2727 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2647 _refine_ls_R_factor_obs 0.0955 _refine_ls_wR_factor_all 0.1568 _refine_ls_wR_factor_obs 0.1182 _refine_ls_goodness_of_fit_all 1.026 _refine_ls_goodness_of_fit_obs 1.200 _refine_ls_restrained_S_all 1.026 _refine_ls_restrained_S_obs 1.200 _refine_ls_shift/esd_max 0.018 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.3560(4) 0.0407(3) 0.9399(5) 0.0493(15) Uani 1 d . . O1A O 0.3578(10) -0.0007(7) 1.0503(14) 0.096(5) Uani 1 d . . O2A O 0.4399(9) 0.0371(9) 0.8853(11) 0.086(5) Uani 1 d . . O3A O 0.3340(9) 0.1190(8) 0.9637(15) 0.123(7) Uani 1 d . . O4A O 0.2901(8) 0.0083(7) 0.8638(12) 0.073(5) Uani 1 d . . Cl2 Cl 0.7408(5) -0.0561(4) 0.8458(6) 0.072(2) Uani 1 d . . O5A O 0.7836(13) -0.1028(8) 0.7683(16) 0.161(9) Uani 1 d . . O6A O 0.7368(15) -0.0849(16) 0.9576(19) 0.251(15) Uani 1 d . . O7A O 0.6561(13) -0.0430(15) 0.8152(18) 0.194(11) Uani 1 d . . O8A O 0.7763(16) 0.0111(11) 0.8447(25) 0.239(15) Uani 1 d . . N1' N 0.0379(9) 0.1738(8) 0.4870(12) 0.042(5) Uani 1 d . . N2 N -0.0163(8) 0.0786(6) 0.6721(12) 0.027(4) Uani 1 d . . N5 N 0.0620(8) 0.2474(7) 0.9250(11) 0.028(4) Uani 1 d . . N11 N 0.1319(8) 0.1728(7) 0.6974(11) 0.032(4) Uani 1 d . . O16 O -0.0486(7) 0.3520(6) 0.7635(11) 0.049(4) Uani 1 d . . O17 O -0.1646(7) 0.2754(5) 0.7240(10) 0.046(4) Uani 1 d . . O20 O 0.0741(8) 0.1252(6) 1.0808(9) 0.049(4) Uani 1 d . . O21 O 0.0920(8) 0.0089(6) 0.9875(9) 0.047(4) Uani 1 d . . O23 O -0.0820(7) 0.1883(6) 0.9373(10) 0.036(3) Uani 1 d . . H23O H -0.0781 0.1338(84) 0.9634(129) 0.050 Uiso 1 d . . C1 C 0.0175(10) 0.0507(10) 0.7894(14) 0.033(5) Uiso 1 d . . H1C1 H 0.0634 0.0122 0.7758 0.060 Uiso 1 calc . . H2C1 H -0.0303 0.0250 0.8312 0.060 Uiso 1 calc . . C3 C -0.0759(10) 0.1467(8) 0.6872(14) 0.029(5) Uiso 1 d . . H1C3 H -0.1253 0.1326 0.7374 0.060 Uiso 1 calc . . H2C3 H -0.0989 0.1628 0.6110 0.060 Uiso 1 calc . . C4 C -0.0245(10) 0.2133(8) 0.7430(14) 0.020(4) Uiso 1 d . . C4A C -0.0031(11) 0.1914(10) 0.8741(16) 0.031(5) Uiso 1 d . . C6 C 0.0403(10) 0.3086(9) 0.9935(14) 0.022(4) Uiso 1 d . . HC6 H -0.0184 0.3220 1.0072 0.060 Uiso 1 calc . . C7 C 0.1102(11) 0.3513(9) 1.0434(15) 0.033(5) Uiso 1 d . . HC7 H 0.0981 0.3935 1.0927 0.060 Uiso 1 calc . . C8 C 0.1957(11) 0.3313(9) 1.0203(15) 0.039(5) Uiso 1 d . . HC8 H 0.2417 0.3602 1.0532 0.060 Uiso 1 calc . . C9 C 0.2142(11) 0.2688(9) 0.9486(15) 0.034(5) Uiso 1 d . . HC9 H 0.2725 0.2555 0.9321 0.060 Uiso 1 calc . . C9A C 0.1458(11) 0.2258(8) 0.9011(13) 0.020(4) Uiso 1 d . . C10 C 0.1415(11) 0.1527(8) 0.8242(14) 0.024(4) Uiso 1 d . . H10 H 0.1923 0.1184 0.8378 0.060 Uiso 1 calc . . C10A C 0.0549(10) 0.1155(8) 0.8679(13) 0.019(4) Uiso 1 d . . C12 C 0.0632(10) 0.2352(8) 0.6776(12) 0.023(4) Uiso 1 d . . H12 H 0.0853 0.2851 0.7083 0.060 Uiso 1 calc . . C13 C -0.0657(11) 0.0134(9) 0.6145(15) 0.045(6) Uiso 1 d . . H131 H -0.0271 -0.0306 0.6044 0.060 Uiso 1 calc . . H132 H -0.0870 0.0302 0.5387 0.060 Uiso 1 calc . . H133 H -0.1148 -0.0014 0.6634 0.060 Uiso 1 calc . . C14 C 0.2171(11) 0.1929(9) 0.6457(16) 0.049(6) Uiso 1 d . . H141 H 0.2093 0.2056 0.5636 0.060 Uiso 1 calc . . H142 H 0.2566 0.1493 0.6528 0.060 Uiso 1 calc . . H143 H 0.2414 0.2371 0.6865 0.060 Uiso 1 calc . . C15 C -0.0811(12) 0.2897(10) 0.7450(18) 0.043(6) Uiso 1 d . . C18 C -0.2209(13) 0.3441(11) 0.7231(18) 0.075(7) Uiso 1 d . . H181 H -0.2811 0.3287 0.7092 0.060 Uiso 1 calc . . H182 H -0.2021 0.3789 0.6615 0.060 Uiso 1 calc . . H183 H -0.2169 0.3702 0.7981 0.060 Uiso 1 calc . . C19 C 0.0744(12) 0.0875(10) 0.9928(16) 0.031(5) Uiso 1 d . . C22 C 0.1220(13) -0.0222(11) 1.0969(17) 0.071(7) Uiso 1 d . . H221 H 0.1346 -0.0769 1.0877 0.060 Uiso 1 calc . . H222 H 0.0770 -0.0155 1.1559 0.060 Uiso 1 calc . . H223 H 0.1747 0.0046 1.1212 0.060 Uiso 1 calc . . C2' C 0.0494(10) 0.2419(9) 0.5453(14) 0.026(5) Uiso 1 d . . C3' C 0.0537(12) 0.3138(12) 0.4892(18) 0.062(6) Uiso 1 d . . H3' H 0.0672 0.3593 0.5303 0.060 Uiso 1 calc . . C4' C 0.0364(14) 0.3142(14) 0.3666(21) 0.085(8) Uiso 1 d . . H4' H 0.0347 0.3612 0.3253 0.060 Uiso 1 calc . . C5' C 0.0222(14) 0.2456(14) 0.3095(19) 0.093(8) Uiso 1 d . . H5' H 0.0103 0.2462 0.2288 0.060 Uiso 1 calc . . C6' C 0.0251(14) 0.1731(13) 0.3697(20) 0.073(7) Uiso 1 d . . H6' H 0.0183 0.1263 0.3289 0.060 Uiso 1 calc . . O1W O -0.1134(10) 0.0606(8) 1.0651(14) 0.075(6) Uiso 1 d . . H1OW H -0.1347(126) 0.0376(104) 1.0279(159) 0.080 Uiso 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 Cl1 0.047(4) 0.037(3) 0.064(4) -0.007(4) -0.014(4) 0.005(3) O1A 0.113(13) 0.086(10) 0.089(13) 0.036(10) -0.017(13) -0.001(11) O2A 0.048(10) 0.134(13) 0.075(12) -0.029(11) 0.018(9) -0.020(11) O3A 0.126(14) 0.051(10) 0.192(19) -0.022(12) -0.072(14) 0.031(10) O4A 0.048(9) 0.090(11) 0.080(12) -0.048(9) -0.013(9) -0.027(8) Cl2 0.074(5) 0.073(5) 0.070(5) -0.013(4) 0.026(5) 0.000(4) O5A 0.264(24) 0.057(10) 0.162(18) -0.008(12) 0.135(19) 0.063(13) O6A 0.216(26) 0.417(40) 0.119(19) 0.084(23) 0.113(20) 0.193(27) O7A 0.089(15) 0.352(30) 0.139(20) -0.097(22) 0.019(17) -0.004(21) O8A 0.236(27) 0.102(17) 0.380(40) -0.142(21) 0.120(26) -0.086(18) N1' 0.055(12) 0.054(12) 0.018(9) -0.003(8) 0.008(9) 0.005(9) N2 0.030(8) 0.008(7) 0.042(10) 0.003(7) -0.018(9) 0.002(6) N5 0.040(10) 0.017(7) 0.028(8) -0.014(7) -0.006(9) 0.004(7) N11 0.019(9) 0.031(9) 0.048(10) 0.009(8) 0.007(9) 0.013(8) O16 0.044(9) 0.029(7) 0.074(10) 0.001(8) 0.006(8) 0.020(6) O17 0.048(9) 0.020(7) 0.071(10) -0.010(6) -0.027(8) 0.026(6) O20 0.069(10) 0.059(8) 0.018(8) 0.009(7) -0.009(8) 0.004(8) O21 0.060(9) 0.047(8) 0.033(8) 0.012(7) -0.024(8) 0.010(7) O23 0.041(8) 0.027(6) 0.041(8) 0.006(7) 0.009(8) -0.008(6) _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 Cl1 O3A 1.408(13) . ? Cl1 O2A 1.412(12) . ? Cl1 O4A 1.430(12) . ? Cl1 O1A 1.435(13) . ? Cl2 O8A 1.27(2) . ? Cl2 O7A 1.35(2) . ? Cl2 O5A 1.351(14) . ? Cl2 O6A 1.36(2) . ? N1' C2' 1.35(2) . ? N1' C6' 1.34(2) . ? N2 C13 1.49(2) . ? N2 C3 1.48(2) . ? N2 C1 1.50(2) . ? N5 C6 1.34(2) . ? N5 C9A 1.35(2) . ? N5 C4A 1.49(2) . ? N11 C14 1.46(2) . ? N11 C10 1.48(2) . ? N11 C12 1.51(2) . ? O16 C15 1.19(2) . ? O17 C15 1.31(2) . ? O17 C18 1.45(2) . ? O20 C19 1.19(2) . ? O21 C19 1.37(2) . ? O21 C22 1.42(2) . ? O23 C4A 1.39(2) . ? C1 C10A 1.53(2) . ? C3 C4 1.52(2) . ? C4 C12 1.56(2) . ? C4 C4A 1.56(2) . ? C4 C15 1.56(2) . ? C4A C10A 1.57(2) . ? C6 C7 1.40(2) . ? C7 C8 1.36(2) . ? C8 C9 1.37(2) . ? C9 C9A 1.38(2) . ? C9A C10 1.53(2) . ? C10 C10A 1.54(2) . ? C10A C19 1.52(2) . ? C12 C2' 1.52(2) . ? C2' C3' 1.39(2) . ? C3' C4' 1.41(2) . ? C4' C5' 1.36(3) . ? C5' C6' 1.42(3) . ? 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 O3A Cl1 O2A 109.7(10) . . ? O3A Cl1 O4A 108.7(8) . . ? O2A Cl1 O4A 110.2(8) . . ? O3A Cl1 O1A 108.0(10) . . ? O2A Cl1 O1A 110.0(10) . . ? O4A Cl1 O1A 110.2(9) . . ? O8A Cl2 O7A 104.5(17) . . ? O8A Cl2 O5A 109.1(13) . . ? O7A Cl2 O5A 112.9(14) . . ? O8A Cl2 O6A 110.9(18) . . ? O7A Cl2 O6A 104.9(14) . . ? O5A Cl2 O6A 114.2(13) . . ? C2' N1' C6' 120.6(17) . . ? C13 N2 C3 109.5(12) . . ? C13 N2 C1 108.6(12) . . ? C3 N2 C1 110.8(12) . . ? C6 N5 C9A 124.0(14) . . ? C6 N5 C4A 124.2(13) . . ? C9A N5 C4A 111.6(13) . . ? C14 N11 C10 110.9(13) . . ? C14 N11 C12 112.5(12) . . ? C10 N11 C12 112.1(12) . . ? C15 O17 C18 114.5(14) . . ? C19 O21 C22 113.1(14) . . ? N2 C1 C10A 114.1(14) . . ? N2 C3 C4 109.1(12) . . ? C3 C4 C12 114.7(13) . . ? C3 C4 C4A 108.6(13) . . ? C12 C4 C4A 109.3(12) . . ? C3 C4 C15 110.7(13) . . ? C12 C4 C15 105.7(12) . . ? C4A C4 C15 107.5(14) . . ? O23 C4A N5 113.2(14) . . ? O23 C4A C4 108.6(13) . . ? N5 C4A C4 110.3(14) . . ? O23 C4A C10A 118.1(14) . . ? N5 C4A C10A 100.4(12) . . ? C4 C4A C10A 105.8(13) . . ? N5 C6 C7 117.0(14) . . ? C8 C7 C6 120.5(15) . . ? C7 C8 C9 120.1(16) . . ? C8 C9 C9A 119.6(15) . . ? N5 C9A C9 118.8(14) . . ? N5 C9A C10 107.4(14) . . ? C9 C9A C10 133.8(16) . . ? N11 C10 C10A 108.9(13) . . ? N11 C10 C9A 111.4(12) . . ? C10A C10 C9A 101.1(13) . . ? C1 C10A C10 115.3(12) . . ? C1 C10A C19 112.4(13) . . ? C10 C10A C19 105.3(14) . . ? C1 C10A C4A 114.9(14) . . ? C10 C10A C4A 98.5(12) . . ? C19 C10A C4A 109.2(13) . . ? N11 C12 C4 110.2(12) . . ? N11 C12 C2' 107.1(12) . . ? C4 C12 C2' 111.6(13) . . ? O16 C15 O17 126.8(18) . . ? O16 C15 C4 121.6(17) . . ? O17 C15 C4 111.6(15) . . ? O20 C19 O21 124.8(16) . . ? O20 C19 C10A 127.3(15) . . ? O21 C19 C10A 107.9(14) . . ? N1' C2' C3' 123.3(16) . . ? N1' C2' C12 115.8(14) . . ? C3' C2' C12 120.8(16) . . ? C2' C3' C4' 116.5(21) . . ? C5' C4' C3' 119.4(24) . . ? C4' C5' C6' 121.7(23) . . ? N1' C6' C5' 118.2(21) . . ? _refine_diff_density_max 0.281 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.067