# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_kuhl01e2a _database_code_CSD 152324 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Burschka, Christian' 'Holzgrabe, Ulrike' 'Kuhl, Ulrich' 'von Korff, Modest Graf' _publ_contact_author_name 'Prof D Ulrike Holzgrabe' _publ_contact_author_address ; Prof D Ulrike Holzgrabe Institut fur Pharmazie und Lebensmittelchemie Universitat Wurzburg Am Hubland Wuzburg D-97074 GERMANY ; _publ_contact_author_email '' #================================================================ # 3. TITLE AND AUTHOR LIST _publ_section_title ; stereochemical behaviour of .kappa.-agonistic 2,4-dipyridine 3,7-diazabicyclo[3.3.1]nonanones - influence of the substituent in position N3 ; loop_ _publ_author_name _publ_author_address 'Kuhl, Ulrich' ; Institut f\"ur Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; 'Korff, Modest Graf von' ; Institut f\"ur Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; 'Burschka, Christian' ; Institut f\"ur Anorganische Chemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; 'Holzgrabe, Ulrike' ; Institut f\"ur Pharmazie und Lebensmittelchemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg ; #=========================================================================== # 4. TEXT _publ_section_abstract ; The influence of substitutents in position N3 on the stereochemistry of 2,4-diaryl- substituted 3,7-diazabicyclo[3.3.1]nonan-9-one 1,5-dicarboxylates attracting interest as opioid-like analgesics was studied. Whereas the variations of the substitution pattern of the phenyl rings revealed the cis substituted isomers to be the most thermodynamically stable form, alkyl substituents at N3 of increasing size induce the trans configuration of the phenyl rings. The configuration was ensured by an X-ray analysis and the thermodynamic superiority of the trans was confirmed by semiemirical calculations. However, substituents having unsaturated bonds, such as propargyl and phenylethyl residues stabilise the cis configuration of the phenyl rings. ; _publ_section_comment ; ; _publ_section_experimental ; The diazabicyclononanones were synthesised according to: U. Kuhl, W. Englberger, M. Haurand, U. Holzgrabe, Arch. Pharm. Pharm. Med. Chem. 2000, 333, 226-230 ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #========================================================================= #data_kuhl01e _audit_creation_method SHELXL-97 _chemical_name_systematic ; dimethyl 3-butyl-7-methyl-2,4 (trans)-di-2-pyridyl-3,7-diazabicyclo[3.3.1] nona-9-one 1,5-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 N4 O5' _chemical_formula_sum 'C26 H32 N4 O5' _chemical_formula_weight 480.56 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 10.686(2) _cell_length_b 14.150(3) _cell_length_c 16.281(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2461.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 8.3 _cell_measurement_theta_max 22.1 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.091 _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 173(2) _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 Stoe-IPDS _diffrn_measurement_method Stoe-IPDS _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11383 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _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 3.45 _diffrn_reflns_theta_max 26.97 _reflns_number_total 5105 _reflns_number_gt 4686 _reflns_threshold_expression >2sigma(I) _computing_data_collection Stoe-IPDS _computing_cell_refinement Stoe-IPDS _computing_data_reduction Stoe-IPDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Bruker-SHELXTL _computing_publication_material Bruker-SHELXTL _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^)+(0.0504P)^2^+0.0891P] 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 0.1(6) _refine_ls_number_reflns 5105 _refine_ls_number_parameters 320 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.29447(13) -1.02977(9) -0.33037(8) 0.0221(3) Uani 1 1 d . . . C2 C 0.27931(12) -1.02062(9) -0.23325(8) 0.0212(2) Uani 1 1 d . . . H2 H 0.3396 -0.9701 -0.2167 0.025 Uiso 1 1 calc R . . C4 C 0.05619(12) -1.03323(9) -0.25111(8) 0.0206(2) Uani 1 1 d . . . H4 H 0.0751 -1.1020 -0.2444 0.025 Uiso 1 1 calc R . . C5 C 0.05984(12) -1.01741(9) -0.34693(8) 0.0221(2) Uani 1 1 d . . . C6 C 0.05985(13) -1.11606(9) -0.38876(8) 0.0238(3) Uani 1 1 d . . . H6A H -0.0218 -1.1476 -0.3799 0.029 Uiso 1 1 calc R . . H6B H 0.0730 -1.1090 -0.4486 0.029 Uiso 1 1 calc R . . C8 C 0.28207(13) -1.13064(9) -0.36885(8) 0.0236(3) Uani 1 1 d . . . H8A H 0.2958 -1.1264 -0.4289 0.028 Uiso 1 1 calc R . . H8B H 0.3478 -1.1721 -0.3457 0.028 Uiso 1 1 calc R . . C9 C 0.18700(13) -0.97377(9) -0.36819(8) 0.0227(3) Uani 1 1 d . . . C10 C 0.14907(13) -0.88215(9) -0.20196(8) 0.0235(3) Uani 1 1 d . . . H10A H 0.0601 -0.8627 -0.2012 0.028 Uiso 1 1 calc R . . H10B H 0.1886 -0.8542 -0.2513 0.028 Uiso 1 1 calc R . . C11 C 0.21417(15) -0.84467(10) -0.12525(10) 0.0330(3) Uani 1 1 d . . . H11A H 0.3047 -0.8591 -0.1285 0.040 Uiso 1 1 calc R . . H11B H 0.1800 -0.8771 -0.0763 0.040 Uiso 1 1 calc R . . C12 C 0.19633(15) -0.73792(10) -0.11587(10) 0.0341(3) Uani 1 1 d . . . H12A H 0.2547 -0.7142 -0.0734 0.041 Uiso 1 1 calc R . . H12B H 0.2179 -0.7067 -0.1684 0.041 Uiso 1 1 calc R . . C13 C 0.0649(2) -0.71131(15) -0.09238(18) 0.0658(6) Uani 1 1 d . . . H13A H 0.0614 -0.6436 -0.0798 0.099 Uiso 1 1 calc R . . H13B H 0.0394 -0.7476 -0.0439 0.099 Uiso 1 1 calc R . . H13C H 0.0082 -0.7253 -0.1381 0.099 Uiso 1 1 calc R . . C14 C 0.15674(15) -1.27028(9) -0.38373(9) 0.0307(3) Uani 1 1 d . . . H14A H 0.2235 -1.3069 -0.3575 0.046 Uiso 1 1 calc R . . H14B H 0.1691 -1.2705 -0.4434 0.046 Uiso 1 1 calc R . . H14C H 0.0755 -1.2987 -0.3706 0.046 Uiso 1 1 calc R . . C16 C 0.41791(13) -0.98275(9) -0.35550(9) 0.0263(3) Uani 1 1 d . . . C19 C 0.58208(18) -0.97931(14) -0.45235(14) 0.0522(5) Uani 1 1 d . . . H19A H 0.6103 -1.0124 -0.5019 0.078 Uiso 1 1 calc R . . H19B H 0.6466 -0.9840 -0.4098 0.078 Uiso 1 1 calc R . . H19C H 0.5670 -0.9126 -0.4653 0.078 Uiso 1 1 calc R . . C20 C 0.32184(12) -1.10854(9) -0.18747(8) 0.0227(3) Uani 1 1 d . . . C21 C 0.25701(14) -1.14622(10) -0.12116(8) 0.0271(3) Uani 1 1 d . . . H21 H 0.1797 -1.1196 -0.1041 0.033 Uiso 1 1 calc R . . C22 C 0.30754(15) -1.22353(10) -0.08037(9) 0.0318(3) Uani 1 1 d . . . H22 H 0.2641 -1.2518 -0.0358 0.038 Uiso 1 1 calc R . . C23 C 0.42215(15) -1.25874(10) -0.10561(9) 0.0322(3) Uani 1 1 d . . . H23 H 0.4596 -1.3109 -0.0783 0.039 Uiso 1 1 calc R . . C24 C 0.48076(15) -1.21604(10) -0.17169(9) 0.0309(3) Uani 1 1 d . . . H24 H 0.5595 -1.2401 -0.1888 0.037 Uiso 1 1 calc R . . C26 C -0.04059(13) -0.95417(10) -0.38403(8) 0.0256(3) Uani 1 1 d . . . C29 C -0.14134(19) -0.80641(12) -0.36969(12) 0.0466(4) Uani 1 1 d . . . H29A H -0.1381 -0.7499 -0.3349 0.070 Uiso 1 1 calc R . . H29B H -0.2262 -0.8327 -0.3688 0.070 Uiso 1 1 calc R . . H29C H -0.1189 -0.7894 -0.4262 0.070 Uiso 1 1 calc R . . C30 C -0.07218(12) -1.02186(8) -0.21284(8) 0.0215(2) Uani 1 1 d . . . C31 C -0.08853(14) -0.99731(9) -0.13061(8) 0.0250(3) Uani 1 1 d . . . H31 H -0.0190 -0.9804 -0.0973 0.030 Uiso 1 1 calc R . . C32 C -0.20840(14) -0.99809(10) -0.09868(9) 0.0295(3) Uani 1 1 d . . . H32 H -0.2224 -0.9810 -0.0430 0.035 Uiso 1 1 calc R . . C33 C -0.30763(15) -1.02386(10) -0.14810(9) 0.0314(3) Uani 1 1 d . . . H33 H -0.3906 -1.0255 -0.1272 0.038 Uiso 1 1 calc R . . C34 C -0.28276(14) -1.04716(11) -0.22870(9) 0.0317(3) Uani 1 1 d . . . H34 H -0.3511 -1.0643 -0.2630 0.038 Uiso 1 1 calc R . . N3 N 0.15666(10) -0.98629(7) -0.20689(7) 0.0217(2) Uani 1 1 d . . . N7 N 0.15989(11) -1.17285(8) -0.35341(7) 0.0235(2) Uani 1 1 d . . . N25 N 0.43245(11) -1.14283(8) -0.21265(7) 0.0272(2) Uani 1 1 d . . . N35 N -0.16790(11) -1.04694(9) -0.26141(7) 0.0277(2) Uani 1 1 d . . . O15 O 0.20108(10) -0.90752(7) -0.41439(6) 0.0305(2) Uani 1 1 d . . . O17 O 0.46381(11) -0.91690(8) -0.32047(7) 0.0375(3) Uani 1 1 d . . . O18 O 0.46731(11) -1.02202(8) -0.42287(7) 0.0378(3) Uani 1 1 d . . . O27 O -0.09446(11) -0.97009(8) -0.44745(6) 0.0356(2) Uani 1 1 d . . . O28 O -0.05435(10) -0.87579(7) -0.33915(6) 0.0294(2) Uani 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 C1 0.0203(6) 0.0214(6) 0.0248(6) -0.0001(5) 0.0019(5) -0.0013(5) C2 0.0179(6) 0.0218(6) 0.0240(6) -0.0011(4) -0.0002(5) -0.0017(5) C4 0.0195(6) 0.0215(5) 0.0209(6) -0.0019(5) -0.0011(5) 0.0001(5) C5 0.0204(6) 0.0249(6) 0.0210(6) -0.0008(5) -0.0009(5) 0.0007(5) C6 0.0220(6) 0.0270(6) 0.0225(6) -0.0039(5) 0.0004(5) -0.0020(5) C8 0.0219(6) 0.0232(6) 0.0258(6) -0.0026(5) 0.0026(5) -0.0004(5) C9 0.0250(7) 0.0232(6) 0.0200(6) -0.0035(4) 0.0017(5) -0.0012(5) C10 0.0221(6) 0.0225(6) 0.0259(6) -0.0033(5) -0.0022(5) 0.0009(5) C11 0.0336(8) 0.0285(7) 0.0369(7) -0.0074(6) -0.0110(6) 0.0011(6) C12 0.0357(8) 0.0286(7) 0.0382(8) -0.0097(6) -0.0018(7) -0.0024(6) C13 0.0461(11) 0.0413(9) 0.1098(18) -0.0311(11) 0.0158(12) -0.0006(9) C14 0.0343(8) 0.0228(6) 0.0349(7) -0.0036(5) 0.0047(6) -0.0030(5) C16 0.0212(6) 0.0262(6) 0.0315(7) 0.0055(5) 0.0025(6) 0.0000(5) C19 0.0418(10) 0.0555(10) 0.0593(11) -0.0020(9) 0.0273(9) -0.0160(8) C20 0.0211(6) 0.0218(6) 0.0252(6) -0.0017(5) -0.0034(5) -0.0016(5) C21 0.0248(6) 0.0293(6) 0.0273(6) -0.0013(5) -0.0011(6) 0.0000(5) C22 0.0391(8) 0.0291(7) 0.0273(7) 0.0032(5) -0.0004(6) -0.0023(6) C23 0.0383(8) 0.0239(6) 0.0344(7) 0.0009(5) -0.0083(6) 0.0029(6) C24 0.0268(7) 0.0280(7) 0.0378(7) -0.0016(6) -0.0038(6) 0.0048(6) C26 0.0223(6) 0.0293(6) 0.0252(6) 0.0002(5) -0.0014(5) 0.0008(5) C29 0.0484(10) 0.0364(8) 0.0551(11) -0.0015(7) -0.0168(8) 0.0161(7) C30 0.0195(6) 0.0209(5) 0.0241(6) 0.0003(5) 0.0001(5) -0.0003(5) C31 0.0257(6) 0.0256(6) 0.0236(6) -0.0012(5) -0.0015(5) 0.0005(5) C32 0.0334(7) 0.0298(6) 0.0252(6) -0.0029(5) 0.0052(6) 0.0010(6) C33 0.0240(7) 0.0333(7) 0.0369(8) -0.0053(6) 0.0078(6) 0.0002(6) C34 0.0212(7) 0.0406(8) 0.0332(7) -0.0061(6) -0.0008(6) -0.0021(6) N3 0.0192(5) 0.0208(5) 0.0250(5) -0.0029(4) -0.0017(4) 0.0008(4) N7 0.0242(5) 0.0217(5) 0.0246(5) -0.0025(4) 0.0019(4) -0.0021(4) N25 0.0221(6) 0.0276(5) 0.0320(6) 0.0002(5) -0.0019(5) 0.0009(5) N35 0.0214(6) 0.0348(6) 0.0270(6) -0.0052(5) -0.0005(5) -0.0025(5) O15 0.0331(6) 0.0282(5) 0.0302(5) 0.0065(4) 0.0023(4) -0.0009(4) O17 0.0319(6) 0.0341(5) 0.0467(6) -0.0026(5) 0.0045(5) -0.0121(5) O18 0.0323(6) 0.0397(6) 0.0415(6) -0.0034(5) 0.0157(5) -0.0097(5) O27 0.0337(6) 0.0466(6) 0.0265(5) -0.0036(4) -0.0096(5) 0.0067(5) O28 0.0313(5) 0.0258(5) 0.0310(5) -0.0017(4) -0.0059(4) 0.0065(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 C1 C9 1.5251(18) . ? C1 C16 1.5330(18) . ? C1 C8 1.5643(17) . ? C1 C2 1.5946(17) . ? C2 N3 1.4622(17) . ? C2 C20 1.5199(18) . ? C4 N3 1.4533(16) . ? C4 C30 1.5153(18) . ? C4 C5 1.5765(18) . ? C5 C26 1.5223(18) . ? C5 C9 1.5321(18) . ? C5 C6 1.5531(18) . ? C6 N7 1.4560(18) . ? C8 N7 1.4576(17) . ? C9 O15 1.2113(16) . ? C10 N3 1.4779(16) . ? C10 C11 1.5248(19) . ? C11 C12 1.530(2) . ? C12 C13 1.503(2) . ? C14 N7 1.4646(17) . ? C16 O17 1.1974(18) . ? C16 O18 1.3382(18) . ? C19 O18 1.4491(19) . ? C20 N25 1.3419(18) . ? C20 C21 1.389(2) . ? C21 C22 1.389(2) . ? C22 C23 1.385(2) . ? C23 C24 1.384(2) . ? C24 N25 1.3357(18) . ? C26 O27 1.2034(17) . ? C26 O28 1.3362(17) . ? C29 O28 1.4404(18) . ? C30 N35 1.3406(18) . ? C30 C31 1.3941(19) . ? C31 C32 1.383(2) . ? C32 C33 1.380(2) . ? C33 C34 1.379(2) . ? C34 N35 1.3380(19) . ? 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 C9 C1 C16 108.34(10) . . ? C9 C1 C8 104.39(10) . . ? C16 C1 C8 111.23(11) . . ? C9 C1 C2 106.35(10) . . ? C16 C1 C2 108.47(10) . . ? C8 C1 C2 117.55(10) . . ? N3 C2 C20 113.33(10) . . ? N3 C2 C1 114.15(10) . . ? C20 C2 C1 112.92(10) . . ? N3 C4 C30 114.62(10) . . ? N3 C4 C5 114.02(10) . . ? C30 C4 C5 114.47(10) . . ? C26 C5 C9 107.38(11) . . ? C26 C5 C6 110.75(10) . . ? C9 C5 C6 105.26(10) . . ? C26 C5 C4 117.30(11) . . ? C9 C5 C4 107.62(10) . . ? C6 C5 C4 107.84(10) . . ? N7 C6 C5 108.83(10) . . ? N7 C8 C1 112.38(10) . . ? O15 C9 C1 124.01(12) . . ? O15 C9 C5 124.22(12) . . ? C1 C9 C5 111.55(10) . . ? N3 C10 C11 111.48(11) . . ? C10 C11 C12 111.61(12) . . ? C13 C12 C11 112.89(14) . . ? O17 C16 O18 123.50(13) . . ? O17 C16 C1 124.27(13) . . ? O18 C16 C1 112.21(11) . . ? N25 C20 C21 122.55(12) . . ? N25 C20 C2 114.18(11) . . ? C21 C20 C2 123.10(12) . . ? C20 C21 C22 118.68(13) . . ? C23 C22 C21 119.04(14) . . ? C24 C23 C22 118.29(13) . . ? N25 C24 C23 123.49(14) . . ? O27 C26 O28 124.88(13) . . ? O27 C26 C5 124.59(13) . . ? O28 C26 C5 110.40(11) . . ? N35 C30 C31 122.46(13) . . ? N35 C30 C4 114.84(11) . . ? C31 C30 C4 122.33(12) . . ? C32 C31 C30 118.38(13) . . ? C33 C32 C31 119.65(13) . . ? C34 C33 C32 118.04(14) . . ? N35 C34 C33 123.70(14) . . ? C4 N3 C2 111.40(10) . . ? C4 N3 C10 116.23(10) . . ? C2 N3 C10 113.35(10) . . ? C6 N7 C8 111.31(10) . . ? C6 N7 C14 111.68(11) . . ? C8 N7 C14 110.38(10) . . ? C24 N25 C20 117.93(12) . . ? C34 N35 C30 117.77(12) . . ? C16 O18 C19 115.61(13) . . ? C26 O28 C29 116.61(12) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.178 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.030 #===END _eof # End