# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_X _database_code_depnum_ccdc_archive 'CCDC 866640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4,8-bis(4-phenoxyphenyl)-1,5-naphthyridine _chemical_melting_point ? _chemical_formula_moiety 'C32 H22 N2 O2' _chemical_formula_sum 'C32 H22 N2 O2' _chemical_formula_weight 466.52 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 Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.869(2) _cell_length_b 14.785(3) _cell_length_c 16.173(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.51(3) _cell_angle_gamma 90.00 _cell_volume 2348.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details '(North, Phillips & Mathews,1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 4573 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.37 _reflns_number_total 4310 _reflns_number_gt 1960 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0600P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4310 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1729 _refine_ls_R_factor_gt 0.0756 _refine_ls_wR_factor_ref 0.1725 _refine_ls_wR_factor_gt 0.1411 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.005 _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 0.8341(3) 0.91590(16) 0.71164(16) 0.0594(8) Uani 1 1 d . . . N1 N 0.9503(3) 0.3844(2) 0.5293(2) 0.0600(10) Uani 1 1 d . . . C1 C 0.8623(4) 0.9939(2) 0.5814(2) 0.0506(10) Uani 1 1 d . . . H1B H 0.8446 0.9413 0.5507 0.061 Uiso 1 1 calc R . . C2 C 0.8886(4) 1.0740(2) 0.5429(2) 0.0549(10) Uani 1 1 d . . . H2A H 0.8919 1.0750 0.4856 0.066 Uiso 1 1 calc R . . C3 C 0.9100(4) 1.1519(3) 0.5871(3) 0.0626(12) Uani 1 1 d . . . H3A H 0.9250 1.2060 0.5600 0.075 Uiso 1 1 calc R . . C4 C 0.9091(4) 1.1502(3) 0.6728(3) 0.0613(11) Uani 1 1 d . . . H4A H 0.9253 1.2029 0.7036 0.074 Uiso 1 1 calc R . . C5 C 0.8842(4) 1.0698(2) 0.7122(2) 0.0542(10) Uani 1 1 d . . . H5A H 0.8819 1.0682 0.7695 0.065 Uiso 1 1 calc R . . C6 C 0.8630(4) 0.9936(2) 0.6669(2) 0.0439(9) Uani 1 1 d . . . C7 C 0.8558(4) 0.8329(2) 0.6754(2) 0.0477(9) Uani 1 1 d . . . C8 C 0.9838(3) 0.8082(2) 0.6523(2) 0.0467(9) Uani 1 1 d . . . H8A H 1.0566 0.8482 0.6603 0.056 Uiso 1 1 calc R . . C9 C 1.0015(4) 0.7249(2) 0.6179(2) 0.0474(9) Uani 1 1 d . . . H9A H 1.0855 0.7096 0.6003 0.057 Uiso 1 1 calc R . . C10 C 0.8952(4) 0.6628(2) 0.6090(2) 0.0428(9) Uani 1 1 d . . . C11 C 0.7702(4) 0.6865(2) 0.6354(2) 0.0573(11) Uani 1 1 d . . . H11A H 0.6990 0.6450 0.6314 0.069 Uiso 1 1 calc R . . C12 C 0.7513(4) 0.7722(2) 0.6678(3) 0.0584(11) Uani 1 1 d . . . H12A H 0.6669 0.7882 0.6844 0.070 Uiso 1 1 calc R . . C13 C 0.9143(4) 0.5695(2) 0.5785(2) 0.0501(10) Uani 1 1 d . . . C14 C 0.8556(4) 0.4970(2) 0.6153(3) 0.0630(12) Uani 1 1 d . . . H14A H 0.8020 0.5078 0.6585 0.076 Uiso 1 1 calc R . . C15 C 0.8743(4) 0.4084(3) 0.5897(2) 0.0644(13) Uani 1 1 d . . . H15A H 0.8308 0.3627 0.6166 0.077 Uiso 1 1 calc R . . C16 C 0.9937(4) 0.5467(2) 0.5114(2) 0.0445(9) Uani 1 1 d . . . O2 O 0.3377(3) 0.91306(15) 0.71376(16) 0.0575(8) Uani 1 1 d . . . N2 N 0.4533(3) 0.3832(2) 0.5284(2) 0.0570(9) Uani 1 1 d . . . C17 C 0.2598(4) 1.0557(3) 0.6574(3) 0.0600(11) Uani 1 1 d . . . H17A H 0.1774 1.0470 0.6798 0.072 Uiso 1 1 calc R . . C18 C 0.2811(4) 1.1329(3) 0.6147(3) 0.0693(13) Uani 1 1 d . . . H18A H 0.2128 1.1763 0.6071 0.083 Uiso 1 1 calc R . . C19 C 0.4046(4) 1.1468(3) 0.5825(3) 0.0612(12) Uani 1 1 d . . . H19A H 0.4194 1.1994 0.5532 0.073 Uiso 1 1 calc R . . C20 C 0.5037(4) 1.0833(2) 0.5938(3) 0.0627(11) Uani 1 1 d . . . H20A H 0.5863 1.0933 0.5721 0.075 Uiso 1 1 calc R . . C21 C 0.4857(4) 1.0056(3) 0.6359(3) 0.0588(11) Uani 1 1 d . . . H21A H 0.5552 0.9631 0.6436 0.071 Uiso 1 1 calc R . . C22 C 0.3598(4) 0.9904(2) 0.6676(2) 0.0512(10) Uani 1 1 d . . . C23 C 0.3608(3) 0.8303(2) 0.6795(2) 0.0401(9) Uani 1 1 d . . . C24 C 0.3883(4) 0.7592(2) 0.7313(2) 0.0523(10) Uani 1 1 d . . . H24A H 0.3945 0.7680 0.7885 0.063 Uiso 1 1 calc R . . C25 C 0.4070(4) 0.6740(2) 0.6997(2) 0.0478(9) Uani 1 1 d . . . H25A H 0.4250 0.6262 0.7365 0.057 Uiso 1 1 calc R . . C26 C 0.3998(3) 0.6565(2) 0.6131(2) 0.0396(8) Uani 1 1 d U . . C27 C 0.3690(4) 0.7305(2) 0.5618(2) 0.0468(9) Uani 1 1 d U . . H27A H 0.3605 0.7226 0.5044 0.056 Uiso 1 1 calc R . . C28 C 0.3508(3) 0.8152(2) 0.5938(2) 0.0457(9) Uani 1 1 d . . . H28A H 0.3315 0.8635 0.5578 0.055 Uiso 1 1 calc R . . C29 C 0.4162(4) 0.5644(2) 0.5821(2) 0.0447(9) Uani 1 1 d . . . C30 C 0.3660(4) 0.4921(2) 0.6211(3) 0.0582(11) Uani 1 1 d . . . H30A H 0.3186 0.5007 0.6675 0.070 Uiso 1 1 calc R . . C31 C 0.3856(4) 0.4052(2) 0.5917(3) 0.0659(13) Uani 1 1 d . . . H31A H 0.3470 0.3580 0.6194 0.079 Uiso 1 1 calc R . . C32 C 0.5083(4) 0.4548(2) 0.4881(2) 0.0491(10) 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 O1 0.082(2) 0.0423(14) 0.0592(17) -0.0126(14) 0.0323(15) -0.0004(13) N1 0.080(3) 0.0412(19) 0.061(2) 0.0026(18) 0.021(2) -0.0103(18) C1 0.059(2) 0.045(2) 0.050(2) -0.002(2) 0.014(2) 0.0111(18) C2 0.066(3) 0.050(2) 0.050(2) 0.009(2) 0.013(2) 0.017(2) C3 0.061(3) 0.039(2) 0.088(4) 0.003(2) 0.013(3) 0.013(2) C4 0.075(3) 0.043(2) 0.067(3) 0.000(2) 0.010(2) 0.005(2) C5 0.063(3) 0.050(2) 0.052(2) -0.006(2) 0.016(2) 0.0056(19) C6 0.043(2) 0.036(2) 0.054(2) 0.0002(18) 0.0155(18) 0.0108(17) C7 0.044(2) 0.040(2) 0.059(2) -0.002(2) 0.0062(19) -0.0007(18) C8 0.044(2) 0.0397(19) 0.057(2) -0.0066(18) 0.0075(18) -0.0065(16) C9 0.052(2) 0.0354(19) 0.059(2) 0.0019(19) 0.0231(19) 0.0089(17) C10 0.056(2) 0.0298(19) 0.043(2) -0.0064(17) 0.0088(18) -0.0024(18) C11 0.051(2) 0.048(2) 0.075(3) -0.011(2) 0.016(2) -0.0047(19) C12 0.051(3) 0.043(2) 0.086(3) -0.008(2) 0.026(2) 0.0041(19) C13 0.054(3) 0.042(2) 0.055(2) -0.0024(19) 0.009(2) -0.0063(19) C14 0.091(3) 0.036(2) 0.067(3) -0.001(2) 0.035(3) -0.009(2) C15 0.080(3) 0.052(3) 0.066(3) -0.005(2) 0.035(3) -0.017(2) C16 0.049(2) 0.0263(17) 0.059(2) -0.0015(18) 0.0069(19) -0.0003(17) O2 0.082(2) 0.0301(13) 0.0647(18) -0.0030(13) 0.0295(16) 0.0035(13) N2 0.071(2) 0.0421(19) 0.062(2) -0.0022(18) 0.0271(19) -0.0028(17) C17 0.059(3) 0.050(2) 0.076(3) -0.005(2) 0.029(2) 0.000(2) C18 0.065(3) 0.050(3) 0.095(4) -0.003(3) 0.018(3) 0.003(2) C19 0.080(3) 0.040(2) 0.066(3) 0.004(2) 0.016(3) -0.008(2) C20 0.072(3) 0.047(2) 0.074(3) 0.002(2) 0.030(2) 0.006(2) C21 0.055(3) 0.052(2) 0.070(3) -0.008(2) 0.011(2) -0.007(2) C22 0.058(3) 0.038(2) 0.059(2) -0.0120(19) 0.015(2) -0.012(2) C23 0.048(2) 0.031(2) 0.043(2) -0.0071(18) 0.0168(17) -0.0006(16) C24 0.056(2) 0.058(2) 0.046(2) 0.001(2) 0.0169(18) -0.0004(19) C25 0.057(2) 0.034(2) 0.054(2) 0.0049(19) 0.0112(19) 0.0095(17) C26 0.0340(19) 0.0360(19) 0.049(2) 0.0018(17) 0.0079(17) 0.0061(16) C27 0.050(2) 0.043(2) 0.048(2) -0.0081(18) 0.0088(18) 0.0017(18) C28 0.050(2) 0.0357(19) 0.053(2) -0.0011(17) 0.0131(18) -0.0059(17) C29 0.048(2) 0.034(2) 0.053(2) 0.0105(18) 0.0118(19) 0.0069(17) C30 0.068(3) 0.045(2) 0.067(3) -0.003(2) 0.031(2) -0.004(2) C31 0.088(3) 0.037(2) 0.080(3) -0.003(2) 0.044(3) -0.007(2) C32 0.054(2) 0.043(2) 0.052(2) -0.0019(19) 0.0189(19) 0.0065(19) _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 C7 1.386(4) . ? O1 C6 1.402(4) . ? N1 C15 1.336(4) . ? N1 C16 1.359(4) 3_766 ? C1 C2 1.374(5) . ? C1 C6 1.383(5) . ? C1 H1B 0.9300 . ? C2 C3 1.362(5) . ? C2 H2A 0.9300 . ? C3 C4 1.387(5) . ? C3 H3A 0.9300 . ? C4 C5 1.382(5) . ? C4 H4A 0.9300 . ? C5 C6 1.349(5) . ? C5 H5A 0.9300 . ? C7 C12 1.363(5) . ? C7 C8 1.400(5) . ? C8 C9 1.369(4) . ? C8 H8A 0.9300 . ? C9 C10 1.391(4) . ? C9 H9A 0.9300 . ? C10 C11 1.388(5) . ? C10 C13 1.483(4) . ? C11 C12 1.392(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.379(5) . ? C13 C16 1.437(5) . ? C14 C15 1.392(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 N1 1.359(4) 3_766 ? C16 C16 1.438(6) 3_766 ? O2 C23 1.372(4) . ? O2 C22 1.394(4) . ? N2 C31 1.316(4) . ? N2 C32 1.382(5) . ? C17 C18 1.361(5) . ? C17 C22 1.380(5) . ? C17 H17A 0.9300 . ? C18 C19 1.385(5) . ? C18 H18A 0.9300 . ? C19 C20 1.355(5) . ? C19 H19A 0.9300 . ? C20 C21 1.355(5) . ? C20 H20A 0.9300 . ? C21 C22 1.407(5) . ? C21 H21A 0.9300 . ? C23 C24 1.355(4) . ? C23 C28 1.396(4) . ? C24 C25 1.379(4) . ? C24 H24A 0.9300 . ? C25 C26 1.420(5) . ? C25 H25A 0.9300 . ? C26 C27 1.390(4) . ? C26 C29 1.464(5) . ? C27 C28 1.374(4) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 C30 1.359(5) . ? C29 C32 1.445(5) 3_666 ? C30 C31 1.390(5) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C32 C32 1.405(7) 3_666 ? C32 C29 1.445(5) 3_666 ? 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 C7 O1 C6 117.4(3) . . ? C15 N1 C16 116.1(3) . 3_766 ? C2 C1 C6 118.2(4) . . ? C2 C1 H1B 120.9 . . ? C6 C1 H1B 120.9 . . ? C3 C2 C1 121.2(4) . . ? C3 C2 H2A 119.4 . . ? C1 C2 H2A 119.4 . . ? C2 C3 C4 119.6(4) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C6 C5 C4 119.6(4) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C1 121.7(4) . . ? C5 C6 O1 115.6(3) . . ? C1 C6 O1 122.5(3) . . ? C12 C7 O1 118.3(3) . . ? C12 C7 C8 119.9(3) . . ? O1 C7 C8 121.6(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 119.0(3) . . ? C11 C10 C13 118.8(3) . . ? C9 C10 C13 122.0(3) . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C7 C12 C11 120.4(4) . . ? C7 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C16 115.2(3) . . ? C14 C13 C10 120.4(4) . . ? C16 C13 C10 124.4(3) . . ? C13 C14 C15 122.0(4) . . ? C13 C14 H14A 119.0 . . ? C15 C14 H14A 119.0 . . ? N1 C15 C14 124.5(4) . . ? N1 C15 H15A 117.7 . . ? C14 C15 H15A 117.7 . . ? N1 C16 C13 117.8(3) 3_766 . ? N1 C16 C16 123.1(4) 3_766 3_766 ? C13 C16 C16 119.1(4) . 3_766 ? C23 O2 C22 118.3(3) . . ? C31 N2 C32 115.4(3) . . ? C18 C17 C22 120.3(4) . . ? C18 C17 H17A 119.9 . . ? C22 C17 H17A 119.9 . . ? C17 C18 C19 120.0(4) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C20 C19 C18 119.7(4) . . ? C20 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? C21 C20 C19 121.8(4) . . ? C21 C20 H20A 119.1 . . ? C19 C20 H20A 119.1 . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H21A 120.6 . . ? C22 C21 H21A 120.6 . . ? C17 C22 O2 119.4(4) . . ? C17 C22 C21 119.4(4) . . ? O2 C22 C21 121.0(4) . . ? C24 C23 O2 118.2(3) . . ? C24 C23 C28 118.7(3) . . ? O2 C23 C28 123.0(3) . . ? C23 C24 C25 120.4(3) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C24 C25 C26 122.5(3) . . ? C24 C25 H25A 118.8 . . ? C26 C25 H25A 118.8 . . ? C27 C26 C25 115.6(3) . . ? C27 C26 C29 123.6(3) . . ? C25 C26 C29 120.7(3) . . ? C28 C27 C26 121.4(3) . . ? C28 C27 H27A 119.3 . . ? C26 C27 H27A 119.3 . . ? C27 C28 C23 121.3(4) . . ? C27 C28 H28A 119.3 . . ? C23 C28 H28A 119.3 . . ? C30 C29 C32 116.6(3) . 3_666 ? C30 C29 C26 121.1(3) . . ? C32 C29 C26 122.3(3) 3_666 . ? C29 C30 C31 120.0(4) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? N2 C31 C30 126.3(4) . . ? N2 C31 H31A 116.8 . . ? C30 C31 H31A 116.8 . . ? N2 C32 C32 122.5(4) . 3_666 ? N2 C32 C29 118.4(3) . 3_666 ? C32 C32 C29 119.1(4) 3_666 3_666 ? 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 C6 C1 C2 C3 -2.3(6) . . . . ? C1 C2 C3 C4 1.9(6) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ? C3 C4 C5 C6 1.0(6) . . . . ? C4 C5 C6 C1 -1.6(6) . . . . ? C4 C5 C6 O1 -178.0(3) . . . . ? C2 C1 C6 C5 2.2(6) . . . . ? C2 C1 C6 O1 178.4(3) . . . . ? C7 O1 C6 C5 -159.2(3) . . . . ? C7 O1 C6 C1 24.4(5) . . . . ? C6 O1 C7 C12 -126.4(4) . . . . ? C6 O1 C7 C8 58.2(5) . . . . ? C12 C7 C8 C9 3.6(6) . . . . ? O1 C7 C8 C9 178.9(3) . . . . ? C7 C8 C9 C10 -2.9(5) . . . . ? C8 C9 C10 C11 0.1(5) . . . . ? C8 C9 C10 C13 -174.9(3) . . . . ? C9 C10 C11 C12 1.9(6) . . . . ? C13 C10 C11 C12 177.1(4) . . . . ? O1 C7 C12 C11 -177.0(3) . . . . ? C8 C7 C12 C11 -1.5(6) . . . . ? C10 C11 C12 C7 -1.2(6) . . . . ? C11 C10 C13 C14 -37.0(5) . . . . ? C9 C10 C13 C14 138.0(4) . . . . ? C11 C10 C13 C16 143.8(4) . . . . ? C9 C10 C13 C16 -41.2(6) . . . . ? C16 C13 C14 C15 0.9(6) . . . . ? C10 C13 C14 C15 -178.3(4) . . . . ? C16 N1 C15 C14 -3.4(7) 3_766 . . . ? C13 C14 C15 N1 1.0(8) . . . . ? C14 C13 C16 N1 177.5(4) . . . 3_766 ? C10 C13 C16 N1 -3.3(6) . . . 3_766 ? C14 C13 C16 C16 -0.3(6) . . . 3_766 ? C10 C13 C16 C16 178.9(4) . . . 3_766 ? C22 C17 C18 C19 -1.2(7) . . . . ? C17 C18 C19 C20 0.0(7) . . . . ? C18 C19 C20 C21 0.2(7) . . . . ? C19 C20 C21 C22 0.8(6) . . . . ? C18 C17 C22 O2 178.0(4) . . . . ? C18 C17 C22 C21 2.1(6) . . . . ? C23 O2 C22 C17 129.5(4) . . . . ? C23 O2 C22 C21 -54.7(5) . . . . ? C20 C21 C22 C17 -1.9(6) . . . . ? C20 C21 C22 O2 -177.7(3) . . . . ? C22 O2 C23 C24 156.3(3) . . . . ? C22 O2 C23 C28 -26.8(5) . . . . ? O2 C23 C24 C25 177.5(3) . . . . ? C28 C23 C24 C25 0.5(5) . . . . ? C23 C24 C25 C26 0.5(6) . . . . ? C24 C25 C26 C27 -1.6(5) . . . . ? C24 C25 C26 C29 -178.1(3) . . . . ? C25 C26 C27 C28 1.8(5) . . . . ? C29 C26 C27 C28 178.1(3) . . . . ? C26 C27 C28 C23 -0.8(5) . . . . ? C24 C23 C28 C27 -0.4(5) . . . . ? O2 C23 C28 C27 -177.2(3) . . . . ? C27 C26 C29 C30 -139.6(4) . . . . ? C25 C26 C29 C30 36.6(5) . . . . ? C27 C26 C29 C32 43.7(5) . . . 3_666 ? C25 C26 C29 C32 -140.2(4) . . . 3_666 ? C32 C29 C30 C31 -1.6(6) 3_666 . . . ? C26 C29 C30 C31 -178.5(4) . . . . ? C32 N2 C31 C30 -0.5(7) . . . . ? C29 C30 C31 N2 1.9(8) . . . . ? C31 N2 C32 C32 -0.9(7) . . . 3_666 ? C31 N2 C32 C29 -179.9(4) . . . 3_666 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.225 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.046 data_X _database_code_depnum_ccdc_archive 'CCDC 881204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4,8-bis(9,9-dibutyl-9H-fluoren-2-yl)-1,5-naphthyridine _chemical_melting_point 459k _chemical_formula_moiety 'C25 H27 N' _chemical_formula_sum 'C25 H27 N' _chemical_formula_weight 341.48 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/N loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9420(18) _cell_length_b 10.249(2) _cell_length_c 21.626(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.87(3) _cell_angle_gamma 90.00 _cell_volume 1967.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 3852 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3607 _reflns_number_gt 1846 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0750P)^2^+0.6000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3607 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1535 _refine_ls_R_factor_gt 0.0766 _refine_ls_wR_factor_ref 0.1974 _refine_ls_wR_factor_gt 0.1626 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 N N 0.3947(3) 0.6539(3) 0.48441(14) 0.0535(8) Uani 1 1 d . . . C1 C 0.8967(5) 0.5767(5) 0.8665(2) 0.0992(16) Uani 1 1 d . . . H1A H 0.8480 0.5685 0.9035 0.149 Uiso 1 1 calc R . . H1B H 0.8417 0.6371 0.8384 0.149 Uiso 1 1 calc R . . H1C H 0.9976 0.6081 0.8773 0.149 Uiso 1 1 calc R . . C2 C 0.9013(5) 0.4461(5) 0.8356(2) 0.0824(13) Uani 1 1 d . . . H2A H 0.7988 0.4147 0.8257 0.099 Uiso 1 1 calc R . . H2B H 0.9539 0.3853 0.8649 0.099 Uiso 1 1 calc R . . C3 C 0.9767(4) 0.4457(4) 0.77662(17) 0.0604(10) Uani 1 1 d . . . H3A H 0.9255 0.5078 0.7475 0.072 Uiso 1 1 calc R . . H3B H 1.0799 0.4749 0.7865 0.072 Uiso 1 1 calc R . . C4 C 0.9769(4) 0.3141(4) 0.74545(18) 0.0607(10) Uani 1 1 d . . . H4A H 0.8731 0.2885 0.7334 0.073 Uiso 1 1 calc R . . H4B H 1.0205 0.2514 0.7760 0.073 Uiso 1 1 calc R . . C5 C 1.0610(3) 0.3033(3) 0.68788(16) 0.0512(9) Uani 1 1 d . . . C6 C 1.0470(4) 0.1622(3) 0.66307(18) 0.0607(10) Uani 1 1 d . . . H6A H 1.0897 0.1042 0.6960 0.073 Uiso 1 1 calc R . . H6B H 0.9407 0.1414 0.6544 0.073 Uiso 1 1 calc R . . C7 C 1.1209(4) 0.1326(4) 0.60525(18) 0.0668(11) Uani 1 1 d . . . H7A H 1.0646 0.1757 0.5699 0.080 Uiso 1 1 calc R . . H7B H 1.2220 0.1684 0.6103 0.080 Uiso 1 1 calc R . . C8 C 1.1294(5) -0.0108(4) 0.5916(2) 0.0764(12) Uani 1 1 d . . . H8A H 1.0284 -0.0469 0.5866 0.092 Uiso 1 1 calc R . . H8B H 1.1860 -0.0540 0.6269 0.092 Uiso 1 1 calc R . . C9 C 1.2030(5) -0.0391(4) 0.5337(2) 0.0935(15) Uani 1 1 d . . . H9A H 1.2055 -0.1317 0.5271 0.140 Uiso 1 1 calc R . . H9B H 1.3039 -0.0055 0.5387 0.140 Uiso 1 1 calc R . . H9C H 1.1462 0.0018 0.4984 0.140 Uiso 1 1 calc R . . C10 C 1.2268(4) 0.3393(3) 0.70177(17) 0.0529(9) Uani 1 1 d . . . C11 C 1.3354(4) 0.2821(4) 0.74424(19) 0.0676(11) Uani 1 1 d . . . H11A H 1.3102 0.2144 0.7697 0.081 Uiso 1 1 calc R . . C12 C 1.4835(5) 0.3278(4) 0.7482(2) 0.0774(13) Uani 1 1 d . . . H12A H 1.5570 0.2910 0.7771 0.093 Uiso 1 1 calc R . . C13 C 1.5217(4) 0.4262(5) 0.7102(2) 0.0749(12) Uani 1 1 d . . . H13A H 1.6213 0.4539 0.7130 0.090 Uiso 1 1 calc R . . C14 C 1.4149(4) 0.4848(4) 0.66771(19) 0.0656(11) Uani 1 1 d . . . H14A H 1.4413 0.5516 0.6420 0.079 Uiso 1 1 calc R . . C15 C 1.2650(4) 0.4410(3) 0.66440(16) 0.0512(9) Uani 1 1 d . . . C16 C 1.1278(4) 0.4844(3) 0.62544(16) 0.0510(9) Uani 1 1 d . . . C17 C 1.1039(4) 0.5844(3) 0.58295(16) 0.0538(9) Uani 1 1 d . . . H17A H 1.1839 0.6355 0.5734 0.065 Uiso 1 1 calc R . . C18 C 0.9613(4) 0.6076(3) 0.55504(16) 0.0558(9) Uani 1 1 d . . . H18A H 0.9450 0.6767 0.5271 0.067 Uiso 1 1 calc R . . C19 C 0.8380(4) 0.5300(3) 0.56727(16) 0.0524(9) Uani 1 1 d . . . C20 C 0.8645(4) 0.4259(4) 0.60944(16) 0.0530(9) Uani 1 1 d . . . H20A H 0.7856 0.3719 0.6175 0.064 Uiso 1 1 calc R . . C21 C 1.0085(3) 0.4040(3) 0.63889(15) 0.0468(8) Uani 1 1 d . . . C22 C 0.6853(4) 0.5671(3) 0.53784(15) 0.0495(9) Uani 1 1 d . . . C23 C 0.6457(4) 0.6954(4) 0.53336(17) 0.0593(10) Uani 1 1 d . . . H23A H 0.7159 0.7585 0.5480 0.071 Uiso 1 1 calc R . . C24 C 0.5025(4) 0.7342(4) 0.50733(18) 0.0635(10) Uani 1 1 d . . . H24A H 0.4815 0.8231 0.5060 0.076 Uiso 1 1 calc R . . C25 C 0.4290(3) 0.5247(3) 0.48670(14) 0.0464(8) 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 N 0.0528(17) 0.0437(16) 0.0633(19) 0.0063(15) 0.0036(14) 0.0068(14) C1 0.079(3) 0.135(5) 0.085(3) -0.032(3) 0.016(3) 0.003(3) C2 0.075(3) 0.112(4) 0.062(3) -0.003(3) 0.012(2) -0.002(3) C3 0.051(2) 0.074(3) 0.056(2) -0.002(2) 0.0022(17) 0.0043(19) C4 0.057(2) 0.064(2) 0.062(2) 0.007(2) 0.0100(18) -0.0014(19) C5 0.0406(18) 0.061(2) 0.051(2) 0.0039(18) 0.0036(15) 0.0016(16) C6 0.056(2) 0.055(2) 0.071(3) 0.008(2) 0.0050(19) 0.0000(18) C7 0.066(2) 0.066(3) 0.067(3) -0.009(2) 0.002(2) 0.008(2) C8 0.070(3) 0.074(3) 0.083(3) -0.008(2) 0.000(2) 0.007(2) C9 0.079(3) 0.085(3) 0.116(4) -0.027(3) 0.011(3) 0.005(3) C10 0.048(2) 0.048(2) 0.062(2) -0.0024(18) 0.0046(17) 0.0098(16) C11 0.058(2) 0.066(3) 0.076(3) 0.004(2) -0.002(2) 0.002(2) C12 0.060(3) 0.084(3) 0.083(3) -0.016(3) -0.012(2) 0.013(2) C13 0.045(2) 0.090(3) 0.089(3) -0.014(3) 0.002(2) 0.003(2) C14 0.053(2) 0.071(3) 0.076(3) -0.019(2) 0.020(2) -0.004(2) C15 0.0431(19) 0.053(2) 0.057(2) -0.0116(18) 0.0041(16) -0.0052(16) C16 0.0468(19) 0.053(2) 0.052(2) -0.0045(17) 0.0025(16) -0.0020(17) C17 0.046(2) 0.052(2) 0.065(2) 0.0073(19) 0.0084(17) -0.0056(17) C18 0.058(2) 0.054(2) 0.057(2) 0.0133(18) 0.0121(18) 0.0030(18) C19 0.052(2) 0.055(2) 0.050(2) 0.0046(18) 0.0062(16) 0.0104(18) C20 0.0419(19) 0.067(2) 0.052(2) 0.0051(19) 0.0127(15) 0.0019(17) C21 0.0384(17) 0.057(2) 0.0457(19) -0.0027(16) 0.0079(14) -0.0039(16) C22 0.051(2) 0.051(2) 0.048(2) -0.0010(16) 0.0095(16) 0.0028(17) C23 0.054(2) 0.051(2) 0.072(3) -0.0039(19) 0.0026(18) 0.0044(18) C24 0.069(2) 0.048(2) 0.070(3) -0.0023(19) -0.003(2) 0.017(2) C25 0.0482(19) 0.048(2) 0.0442(19) 0.0052(16) 0.0099(15) 0.0072(16) _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 N C24 1.318(4) . ? N C25 1.359(4) . ? C1 C2 1.499(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.512(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.508(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.534(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C21 1.513(4) . ? C5 C10 1.522(4) . ? C5 C6 1.542(5) . ? C6 C7 1.513(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.503(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.511(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.384(5) . ? C10 C15 1.387(5) . ? C11 C12 1.398(5) . ? C11 H11A 0.9300 . ? C12 C13 1.370(6) . ? C12 H12A 0.9300 . ? C13 C14 1.381(5) . ? C13 H13A 0.9300 . ? C14 C15 1.407(5) . ? C14 H14A 0.9300 . ? C15 C16 1.472(5) . ? C16 C17 1.376(5) . ? C16 C21 1.405(4) . ? C17 C18 1.365(4) . ? C17 H17A 0.9300 . ? C18 C19 1.410(5) . ? C18 H18A 0.9300 . ? C19 C20 1.405(5) . ? C19 C22 1.485(5) . ? C20 C21 1.385(4) . ? C20 H20A 0.9300 . ? C22 C23 1.362(4) . ? C22 C25 1.443(4) 3_666 ? C23 C24 1.394(5) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C25 1.423(6) 3_666 ? C25 C22 1.443(4) 3_666 ? 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 C24 N C25 116.3(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 114.6(4) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 113.8(3) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 117.0(3) . . ? C3 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C3 C4 H4B 108.0 . . ? C5 C4 H4B 108.0 . . ? H4A C4 H4B 107.3 . . ? C21 C5 C10 100.7(3) . . ? C21 C5 C4 112.2(3) . . ? C10 C5 C4 112.5(3) . . ? C21 C5 C6 113.0(3) . . ? C10 C5 C6 109.4(3) . . ? C4 C5 C6 108.8(3) . . ? C7 C6 C5 116.8(3) . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6B 108.1 . . ? C5 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C6 113.3(3) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 112.8(4) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 120.1(3) . . ? C11 C10 C5 128.1(3) . . ? C15 C10 C5 111.7(3) . . ? C10 C11 C12 118.9(4) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? C13 C12 C11 120.8(4) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C12 C13 C14 121.2(4) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C13 C14 C15 118.3(4) . . ? C13 C14 H14A 120.9 . . ? C15 C14 H14A 120.9 . . ? C10 C15 C14 120.7(3) . . ? C10 C15 C16 108.3(3) . . ? C14 C15 C16 131.0(4) . . ? C17 C16 C21 120.9(3) . . ? C17 C16 C15 131.3(3) . . ? C21 C16 C15 107.8(3) . . ? C18 C17 C16 119.2(3) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C17 C18 C19 121.9(3) . . ? C17 C18 H18A 119.0 . . ? C19 C18 H18A 119.0 . . ? C20 C19 C18 118.4(3) . . ? C20 C19 C22 123.2(3) . . ? C18 C19 C22 118.3(3) . . ? C21 C20 C19 119.8(3) . . ? C21 C20 H20A 120.1 . . ? C19 C20 H20A 120.1 . . ? C20 C21 C16 119.8(3) . . ? C20 C21 C5 128.7(3) . . ? C16 C21 C5 111.4(3) . . ? C23 C22 C25 115.9(3) . 3_666 ? C23 C22 C19 119.7(3) . . ? C25 C22 C19 124.4(3) 3_666 . ? C22 C23 C24 121.5(4) . . ? C22 C23 H23A 119.2 . . ? C24 C23 H23A 119.2 . . ? N C24 C23 124.7(3) . . ? N C24 H24A 117.7 . . ? C23 C24 H24A 117.7 . . ? N C25 C25 123.2(4) . 3_666 ? N C25 C22 118.4(3) . 3_666 ? C25 C25 C22 118.4(4) 3_666 3_666 ? 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 C1 C2 C3 C4 -178.7(3) . . . . ? C2 C3 C4 C5 -175.8(3) . . . . ? C3 C4 C5 C21 -53.9(4) . . . . ? C3 C4 C5 C10 58.8(4) . . . . ? C3 C4 C5 C6 -179.7(3) . . . . ? C21 C5 C6 C7 53.6(4) . . . . ? C10 C5 C6 C7 -57.8(4) . . . . ? C4 C5 C6 C7 178.9(3) . . . . ? C5 C6 C7 C8 168.4(3) . . . . ? C6 C7 C8 C9 179.8(3) . . . . ? C21 C5 C10 C11 178.9(4) . . . . ? C4 C5 C10 C11 59.3(5) . . . . ? C6 C5 C10 C11 -61.8(5) . . . . ? C21 C5 C10 C15 -2.5(4) . . . . ? C4 C5 C10 C15 -122.1(3) . . . . ? C6 C5 C10 C15 116.7(3) . . . . ? C15 C10 C11 C12 -0.6(6) . . . . ? C5 C10 C11 C12 177.9(3) . . . . ? C10 C11 C12 C13 -1.0(6) . . . . ? C11 C12 C13 C14 1.3(6) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? C11 C10 C15 C14 1.9(5) . . . . ? C5 C10 C15 C14 -176.8(3) . . . . ? C11 C10 C15 C16 -178.5(3) . . . . ? C5 C10 C15 C16 2.8(4) . . . . ? C13 C14 C15 C10 -1.6(5) . . . . ? C13 C14 C15 C16 178.9(4) . . . . ? C10 C15 C16 C17 176.9(4) . . . . ? C14 C15 C16 C17 -3.5(6) . . . . ? C10 C15 C16 C21 -1.9(4) . . . . ? C14 C15 C16 C21 177.7(3) . . . . ? C21 C16 C17 C18 1.9(5) . . . . ? C15 C16 C17 C18 -176.7(3) . . . . ? C16 C17 C18 C19 -1.6(5) . . . . ? C17 C18 C19 C20 -0.1(5) . . . . ? C17 C18 C19 C22 176.3(3) . . . . ? C18 C19 C20 C21 1.6(5) . . . . ? C22 C19 C20 C21 -174.7(3) . . . . ? C19 C20 C21 C16 -1.3(5) . . . . ? C19 C20 C21 C5 176.6(3) . . . . ? C17 C16 C21 C20 -0.5(5) . . . . ? C15 C16 C21 C20 178.5(3) . . . . ? C17 C16 C21 C5 -178.7(3) . . . . ? C15 C16 C21 C5 0.3(4) . . . . ? C10 C5 C21 C20 -176.8(3) . . . . ? C4 C5 C21 C20 -56.9(5) . . . . ? C6 C5 C21 C20 66.6(4) . . . . ? C10 C5 C21 C16 1.3(4) . . . . ? C4 C5 C21 C16 121.1(3) . . . . ? C6 C5 C21 C16 -115.3(3) . . . . ? C20 C19 C22 C23 136.8(4) . . . . ? C18 C19 C22 C23 -39.4(5) . . . . ? C20 C19 C22 C25 -42.5(5) . . . 3_666 ? C18 C19 C22 C25 141.2(3) . . . 3_666 ? C25 C22 C23 C24 0.8(5) 3_666 . . . ? C19 C22 C23 C24 -178.6(3) . . . . ? C25 N C24 C23 -0.3(5) . . . . ? C22 C23 C24 N -0.8(6) . . . . ? C24 N C25 C25 1.4(6) . . . 3_666 ? C24 N C25 C22 -180.0(3) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.170 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.042 data_X2 _database_code_depnum_ccdc_archive 'CCDC 881205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4,8-bis(4-(tert-butyl)phenyl)-1,5-naphthyridine _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N' _chemical_formula_sum 'C14 H15 N' _chemical_formula_weight 197.27 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.973(2) _cell_length_b 7.8020(16) _cell_length_c 12.534(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.95(3) _cell_angle_gamma 90.00 _cell_volume 1141.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description BLOCK _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9868 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2205 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0898 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2101 _reflns_number_gt 1023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0250P)^2^+0.5000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2101 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1810 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 N N 0.4647(2) 0.0394(4) 0.1335(2) 0.0588(8) Uani 1 1 d . . . C1 C 0.9139(4) -0.8184(6) -0.0800(4) 0.138(2) Uani 1 1 d . . . H1A H 0.9555 -0.8974 -0.1151 0.206 Uiso 1 1 calc R . . H1B H 0.8544 -0.8785 -0.0552 0.206 Uiso 1 1 calc R . . H1C H 0.9652 -0.7666 -0.0185 0.206 Uiso 1 1 calc R . . C2 C 0.9509(4) -0.6099(6) -0.2063(4) 0.120 Uani 1 1 d . . . H2A H 0.9196 -0.5252 -0.2604 0.179 Uiso 1 1 calc R . . H2B H 0.9857 -0.6999 -0.2397 0.179 Uiso 1 1 calc R . . H2C H 1.0075 -0.5577 -0.1491 0.179 Uiso 1 1 calc R . . C3 C 0.7756(4) -0.7833(6) -0.2462(4) 0.120 Uani 1 1 d . . . H3A H 0.7366 -0.7081 -0.3031 0.180 Uiso 1 1 calc R . . H3B H 0.7207 -0.8373 -0.2119 0.180 Uiso 1 1 calc R . . H3C H 0.8162 -0.8694 -0.2772 0.180 Uiso 1 1 calc R . . C4 C 0.8607(3) -0.6799(5) -0.1609(3) 0.0670(10) Uani 1 1 d . . . C5 C 0.7914(3) -0.5524(4) -0.1095(3) 0.0554(9) Uani 1 1 d . . . C6 C 0.8041(3) -0.3748(4) -0.1185(3) 0.0538(9) Uani 1 1 d . . . H6A H 0.8574 -0.3334 -0.1558 0.065 Uiso 1 1 calc R . . C7 C 0.7407(2) -0.2607(4) -0.0745(3) 0.0559(10) Uani 1 1 d . . . H7A H 0.7489 -0.1439 -0.0854 0.067 Uiso 1 1 calc R . . C8 C 0.6642(3) -0.3168(4) -0.0136(2) 0.0509(8) Uani 1 1 d . . . C9 C 0.6556(3) -0.4914(4) -0.0003(3) 0.0580(9) Uani 1 1 d . . . H9A H 0.6054 -0.5321 0.0407 0.070 Uiso 1 1 calc R . . C10 C 0.7171(3) -0.6058(4) -0.0444(3) 0.0616(10) Uani 1 1 d . . . H10A H 0.7099 -0.7221 -0.0311 0.074 Uiso 1 1 calc R . . C11 C 0.5960(3) -0.1929(4) 0.0358(3) 0.0520(9) Uani 1 1 d . . . C12 C 0.5865(3) -0.2126(4) 0.1411(3) 0.0607(10) Uani 1 1 d . . . H12A H 0.6206 -0.3054 0.1825 0.073 Uiso 1 1 calc R . . C13 C 0.5238(3) -0.0899(4) 0.1867(3) 0.0635(10) Uani 1 1 d . . . H13A H 0.5241 -0.1010 0.2606 0.076 Uiso 1 1 calc R . . C14 C 0.4678(3) 0.0561(4) 0.0258(3) 0.0499(8) 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 N 0.0595(19) 0.063(2) 0.0515(17) -0.0015(15) 0.0079(15) 0.0091(16) C1 0.168(5) 0.106(4) 0.158(5) 0.019(4) 0.077(4) 0.040(4) C2 0.120 0.120 0.120 0.000 0.027 0.000 C3 0.120 0.120 0.120 0.000 0.027 0.000 C4 0.055(2) 0.065(3) 0.087(3) -0.020(2) 0.028(2) -0.013(2) C5 0.051(2) 0.053(2) 0.061(2) -0.0071(18) 0.0087(18) -0.0018(18) C6 0.052(2) 0.047(2) 0.065(2) 0.0024(17) 0.0175(18) 0.0010(17) C7 0.0379(18) 0.0351(19) 0.092(3) 0.0004(18) 0.0097(19) -0.0021(16) C8 0.055(2) 0.051(2) 0.0455(19) 0.0052(17) 0.0091(17) -0.0002(18) C9 0.069(2) 0.057(2) 0.050(2) 0.0064(18) 0.0180(19) 0.003(2) C10 0.076(3) 0.035(2) 0.078(3) -0.0107(19) 0.025(2) 0.0033(19) C11 0.058(2) 0.051(2) 0.047(2) 0.0013(18) 0.0102(17) 0.0034(18) C12 0.064(2) 0.054(2) 0.064(2) 0.0002(19) 0.0129(19) 0.0097(19) C13 0.077(3) 0.058(2) 0.053(2) 0.0015(19) 0.0078(19) 0.006(2) C14 0.052(2) 0.046(2) 0.053(2) -0.0065(16) 0.0136(16) -0.0082(16) _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 N C13 1.323(4) . ? N C14 1.364(4) . ? C1 C4 1.520(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.436(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.532(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.527(4) . ? C5 C10 1.399(4) . ? C5 C6 1.401(4) . ? C6 C7 1.364(4) . ? C6 H6A 0.9300 . ? C7 C8 1.388(4) . ? C7 H7A 0.9300 . ? C8 C9 1.379(4) . ? C8 C11 1.487(4) . ? C9 C10 1.352(4) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.359(4) . ? C11 C14 1.434(4) 3_655 ? C12 C13 1.413(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C14 1.416(6) 3_655 ? C14 C11 1.434(4) 3_655 ? 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 C13 N C14 116.2(3) . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B 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 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C1 107.2(4) . . ? C2 C4 C5 116.5(4) . . ? C1 C4 C5 111.6(3) . . ? C2 C4 C3 111.4(3) . . ? C1 C4 C3 101.8(4) . . ? C5 C4 C3 107.3(3) . . ? C10 C5 C6 115.8(3) . . ? C10 C5 C4 121.9(3) . . ? C6 C5 C4 122.1(3) . . ? C7 C6 C5 122.2(3) . . ? C7 C6 H6A 118.9 . . ? C5 C6 H6A 118.9 . . ? C6 C7 C8 120.8(3) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C9 C8 C7 117.0(3) . . ? C9 C8 C11 121.9(3) . . ? C7 C8 C11 121.0(3) . . ? C10 C9 C8 122.7(3) . . ? C10 C9 H9A 118.7 . . ? C8 C9 H9A 118.7 . . ? C9 C10 C5 121.2(3) . . ? C9 C10 H10A 119.4 . . ? C5 C10 H10A 119.4 . . ? C12 C11 C14 117.2(3) . 3_655 ? C12 C11 C8 120.3(3) . . ? C14 C11 C8 122.4(3) 3_655 . ? C11 C12 C13 118.9(3) . . ? C11 C12 H12A 120.6 . . ? C13 C12 H12A 120.6 . . ? N C13 C12 125.8(3) . . ? N C13 H13A 117.1 . . ? C12 C13 H13A 117.1 . . ? N C14 C14 122.1(4) . 3_655 ? N C14 C11 118.4(3) . 3_655 ? C14 C14 C11 119.5(4) 3_655 3_655 ? 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 C2 C4 C5 C10 -167.4(3) . . . . ? C1 C4 C5 C10 -43.8(5) . . . . ? C3 C4 C5 C10 67.0(4) . . . . ? C2 C4 C5 C6 8.2(5) . . . . ? C1 C4 C5 C6 131.7(4) . . . . ? C3 C4 C5 C6 -117.5(4) . . . . ? C10 C5 C6 C7 -5.4(5) . . . . ? C4 C5 C6 C7 178.8(3) . . . . ? C5 C6 C7 C8 3.2(5) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C6 C7 C8 C11 179.2(3) . . . . ? C7 C8 C9 C10 -0.5(5) . . . . ? C11 C8 C9 C10 -179.8(3) . . . . ? C8 C9 C10 C5 -1.9(6) . . . . ? C6 C5 C10 C9 4.8(5) . . . . ? C4 C5 C10 C9 -179.4(3) . . . . ? C9 C8 C11 C12 44.7(5) . . . . ? C7 C8 C11 C12 -134.6(3) . . . . ? C9 C8 C11 C14 -131.2(3) . . . 3_655 ? C7 C8 C11 C14 49.6(4) . . . 3_655 ? C14 C11 C12 C13 -5.7(5) 3_655 . . . ? C8 C11 C12 C13 178.2(3) . . . . ? C14 N C13 C12 -1.6(5) . . . . ? C11 C12 C13 N 5.4(6) . . . . ? C13 N C14 C14 -1.2(6) . . . 3_655 ? C13 N C14 C11 179.2(3) . . . 3_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037