# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Qi, Hengzhen' 'Li, Xinyao' 'Xu, Jiaxi' _publ_contact_author_name 'Jiaxi Xu' _publ_contact_author_address ; ; _publ_contact_author_email jxxu@mail.buct.edu.cn data_compound5bb _database_code_depnum_ccdc_archive 'CCDC 804599' #TrackingRef 'compound5bb.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C24 H17 N2 O3' _chemical_formula_sum 'C24 H17 N2 O3' _chemical_formula_weight 381.40 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 'Pna2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.927(3) _cell_length_b 12.667(3) _cell_length_c 18.063(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3873.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8775 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.42 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9241 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 36601 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.42 _reflns_number_total 8775 _reflns_number_gt 5270 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _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^)+(0.0596P)^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 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_number_reflns 8775 _refine_ls_number_parameters 662 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.004 _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 0.39413(12) 0.43141(19) 0.00721(11) 0.0522(6) Uani 1 1 d . . . O2 O 0.59500(12) 0.51125(17) 0.21421(11) 0.0475(5) Uani 1 1 d . . . O3 O 0.50388(17) 0.7399(2) 0.22471(15) 0.0619(8) Uani 1 1 d . . . O4 O 0.13048(12) 0.4385(2) 0.41939(12) 0.0533(6) Uani 1 1 d . . . O5 O 0.32218(15) 0.52184(19) 0.20775(13) 0.0658(7) Uani 1 1 d . . . O6 O 0.25156(18) 0.76020(19) 0.21192(15) 0.0657(8) Uani 1 1 d . . . N1 N 0.22603(14) 0.5106(2) 0.30010(12) 0.0381(6) Uani 1 1 d . . . N2 N 0.30117(19) 0.8432(2) 0.31116(16) 0.0537(8) Uani 1 1 d . . . N3 N 0.49153(13) 0.5030(2) 0.12774(13) 0.0340(6) Uani 1 1 d . . . N4 N 0.55383(17) 0.8393(2) 0.13108(16) 0.0467(7) Uani 1 1 d . . . C1 C 0.45851(16) 0.4018(2) 0.12674(15) 0.0343(7) Uani 1 1 d . . . C2 C 0.41205(18) 0.3674(3) 0.06796(18) 0.0431(8) Uani 1 1 d . . . C3 C 0.3765(2) 0.2695(3) 0.0712(2) 0.0513(9) Uani 1 1 d . . . H3 H 0.339(3) 0.260(3) 0.032(3) 0.098(17) Uiso 1 1 d . . . C4 C 0.3888(2) 0.2031(3) 0.1297(2) 0.0594(10) Uani 1 1 d . . . H4 H 0.3654(17) 0.139(2) 0.1296(16) 0.040(8) Uiso 1 1 d . . . C5 C 0.4371(3) 0.2348(3) 0.1869(2) 0.0590(11) Uani 1 1 d . . . H5 H 0.443(2) 0.196(3) 0.233(2) 0.087(13) Uiso 1 1 d . . . C6 C 0.4718(2) 0.3329(3) 0.18546(18) 0.0448(8) Uani 1 1 d . . . H6 H 0.5076(18) 0.351(2) 0.2217(16) 0.035(8) Uiso 1 1 d . . . C7 C 0.45704(18) 0.4760(3) -0.03261(16) 0.0417(8) Uani 1 1 d . . . C8 C 0.50128(17) 0.5592(2) -0.00267(15) 0.0343(7) Uani 1 1 d . . . C9 C 0.5578(2) 0.6046(3) -0.04794(17) 0.0379(8) Uani 1 1 d . . . H9 H 0.5907(17) 0.651(2) -0.0279(15) 0.029(8) Uiso 1 1 d . . . C10 C 0.5703(2) 0.5702(3) -0.11969(17) 0.0458(8) Uani 1 1 d . . . H10 H 0.609(2) 0.604(3) -0.1465(18) 0.056(10) Uiso 1 1 d . . . C11 C 0.5266(2) 0.4886(3) -0.14813(19) 0.0509(9) Uani 1 1 d . . . H11 H 0.5370(16) 0.470(2) -0.2008(16) 0.047(9) Uiso 1 1 d . . . C12 C 0.4693(2) 0.4405(3) -0.10454(18) 0.0493(9) Uani 1 1 d . . . H12 H 0.436(2) 0.377(3) -0.1167(19) 0.064(11) Uiso 1 1 d . . . C13 C 0.59055(18) 0.8483(2) 0.05924(17) 0.0402(7) Uani 1 1 d . . . C14 C 0.6702(2) 0.8263(3) 0.0512(2) 0.0492(9) Uani 1 1 d . . . H14 H 0.697(2) 0.806(3) 0.092(2) 0.066(11) Uiso 1 1 d . . . C15 C 0.7027(3) 0.8284(3) -0.0190(2) 0.0620(11) Uani 1 1 d . . . H15 H 0.754(3) 0.838(4) -0.022(3) 0.13(2) Uiso 1 1 d . . . C16 C 0.6574(3) 0.8544(3) -0.0795(2) 0.0633(11) Uani 1 1 d . . . H16 H 0.6773(18) 0.850(2) -0.1319(19) 0.048(9) Uiso 1 1 d . . . C17 C 0.5798(3) 0.8824(3) -0.0702(2) 0.0587(10) Uani 1 1 d . . . H17 H 0.537(2) 0.906(3) -0.115(2) 0.086(13) Uiso 1 1 d . . . C18 C 0.5459(2) 0.8781(3) -0.0009(2) 0.0478(9) Uani 1 1 d . . . H18 H 0.4942(19) 0.900(3) 0.0108(18) 0.047(9) Uiso 1 1 d . . . C19 C 0.5347(3) 0.9394(3) 0.1705(2) 0.0830(15) Uani 1 1 d . . . C20 C 0.5362(2) 0.7464(2) 0.1631(2) 0.0424(9) Uani 1 1 d . . . C21 C 0.55352(19) 0.6462(2) 0.11895(16) 0.0332(7) Uani 1 1 d . . . H21 H 0.605(2) 0.645(3) 0.0861(19) 0.068(11) Uiso 1 1 d . . . C22 C 0.55392(19) 0.5460(3) 0.16543(16) 0.0356(7) Uani 1 1 d . . . C23 C 0.48270(16) 0.5943(2) 0.07536(16) 0.0341(7) Uani 1 1 d . . . C24 C 0.40478(17) 0.6528(3) 0.08001(17) 0.0451(8) Uani 1 1 d . . . H24A H 0.3952 0.6736 0.1303 0.080 Uiso 1 1 calc R . . H24B H 0.3629 0.6075 0.0635 0.080 Uiso 1 1 calc R . . H24C H 0.4069 0.7145 0.0491 0.080 Uiso 1 1 calc R . . C25 C 0.19714(17) 0.4069(3) 0.30289(16) 0.0406(7) Uani 1 1 d . . . C26 C 0.15184(18) 0.3713(3) 0.36206(17) 0.0426(8) Uani 1 1 d . . . C27 C 0.1232(2) 0.2689(3) 0.3648(2) 0.0541(10) Uani 1 1 d . . . H27 H 0.092(2) 0.246(3) 0.412(2) 0.055(10) Uiso 1 1 d . . . C28 C 0.1423(2) 0.1990(3) 0.3073(2) 0.0618(10) Uani 1 1 d . . . H28 H 0.1248(19) 0.121(3) 0.313(2) 0.070(11) Uiso 1 1 d . . . C29 C 0.1885(3) 0.2327(3) 0.2499(2) 0.0614(11) Uani 1 1 d . . . H29 H 0.2052(18) 0.182(3) 0.210(2) 0.055(9) Uiso 1 1 d . . . C30 C 0.2164(2) 0.3351(3) 0.2460(2) 0.0527(9) Uani 1 1 d . . . H30 H 0.2476(18) 0.361(2) 0.2032(19) 0.048(9) Uiso 1 1 d . . . C31 C 0.19271(17) 0.4800(3) 0.46166(16) 0.0410(7) Uani 1 1 d . . . C32 C 0.23866(17) 0.5602(2) 0.43320(15) 0.0341(7) Uani 1 1 d . . . C33 C 0.2968(2) 0.6031(3) 0.47804(17) 0.0401(8) Uani 1 1 d . . . H33 H 0.331(2) 0.665(3) 0.4580(19) 0.060(10) Uiso 1 1 d . . . C34 C 0.3087(2) 0.5648(3) 0.54954(16) 0.0454(9) Uani 1 1 d . . . H34 H 0.3528(18) 0.595(2) 0.5795(18) 0.049(9) Uiso 1 1 d . . . C35 C 0.2624(2) 0.4841(3) 0.57546(19) 0.0505(9) Uani 1 1 d . . . H35 H 0.2739(17) 0.454(2) 0.6230(17) 0.047(9) Uiso 1 1 d . . . C36 C 0.2046(2) 0.4420(3) 0.53183(19) 0.0518(9) Uani 1 1 d . . . H36 H 0.174(2) 0.393(3) 0.5495(19) 0.061(11) Uiso 1 1 d . . . C37 C 0.33642(18) 0.8437(2) 0.38317(16) 0.0367(7) Uani 1 1 d . . . C38 C 0.4147(2) 0.8166(3) 0.39169(17) 0.0447(8) Uani 1 1 d . . . H38 H 0.4472(18) 0.799(3) 0.3459(18) 0.049(9) Uiso 1 1 d . . . C39 C 0.4476(2) 0.8169(3) 0.4613(2) 0.0545(9) Uani 1 1 d . . . H39 H 0.5055(19) 0.797(2) 0.4674(15) 0.044(8) Uiso 1 1 d . . . C40 C 0.4047(3) 0.8460(3) 0.52120(19) 0.0558(10) Uani 1 1 d . . . H40 H 0.436(2) 0.849(3) 0.5661(19) 0.063(10) Uiso 1 1 d . . . C41 C 0.3270(3) 0.8761(3) 0.5127(2) 0.0581(12) Uani 1 1 d . . . H41 H 0.2995(19) 0.897(3) 0.5419(17) 0.042(11) Uiso 1 1 d . . . C42 C 0.2927(2) 0.8756(3) 0.4433(2) 0.0462(8) Uani 1 1 d . . . H42 H 0.2399(17) 0.895(2) 0.4396(15) 0.033(8) Uiso 1 1 d . . . C43 C 0.2985(5) 0.9459(9) 0.2697(5) 0.060(2) Uani 0.60 1 d PU . . C43' C 0.2633(8) 0.9500(14) 0.2858(9) 0.060(2) Uani 0.40 1 d PU . . C44 C 0.2796(2) 0.7551(3) 0.2732(2) 0.0435(9) Uani 1 1 d . . . C45 C 0.29236(19) 0.6501(3) 0.31081(18) 0.0366(8) Uani 1 1 d . . . H45 H 0.3438(16) 0.645(2) 0.3361(13) 0.022(7) Uiso 1 1 d . . . C46 C 0.28673(19) 0.5538(3) 0.25991(18) 0.0419(8) Uani 1 1 d . . . C47 C 0.22181(16) 0.5996(2) 0.35529(15) 0.0345(7) Uani 1 1 d . . . C48 C 0.14491(18) 0.6619(3) 0.35030(18) 0.0508(9) Uani 1 1 d . . . H48A H 0.1370 0.6850 0.3002 0.080 Uiso 1 1 calc R . . H48B H 0.1477 0.7222 0.3824 0.080 Uiso 1 1 calc R . . H48C H 0.1016 0.6177 0.3651 0.080 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 O1 0.0461(13) 0.0619(16) 0.0487(13) 0.0119(12) -0.0114(11) -0.0166(11) O2 0.0481(12) 0.0528(14) 0.0416(12) 0.0164(10) -0.0106(11) -0.0060(10) O3 0.0897(19) 0.0558(18) 0.0401(16) -0.0064(11) 0.0182(15) -0.0070(13) O4 0.0419(12) 0.0647(16) 0.0532(14) -0.0178(12) 0.0138(10) -0.0160(11) O5 0.0872(18) 0.0558(15) 0.0544(14) -0.0105(12) 0.0337(14) -0.0085(13) O6 0.104(2) 0.0526(17) 0.0405(16) -0.0027(12) -0.0295(17) -0.0042(14) N1 0.0460(15) 0.0333(15) 0.0351(13) -0.0110(11) 0.0042(11) -0.0028(12) N2 0.077(2) 0.0384(19) 0.0453(17) 0.0036(14) -0.0258(16) -0.0029(14) N3 0.0377(13) 0.0326(13) 0.0317(12) 0.0042(11) -0.0019(11) -0.0026(11) N4 0.0645(18) 0.0304(16) 0.0451(15) -0.0015(13) -0.0009(14) -0.0003(13) C1 0.0339(15) 0.0308(17) 0.0383(16) 0.0054(14) 0.0078(14) 0.0005(13) C2 0.0401(17) 0.047(2) 0.0425(18) 0.0010(16) 0.0034(15) -0.0034(15) C3 0.045(2) 0.050(2) 0.058(2) -0.007(2) 0.0016(19) -0.0185(18) C4 0.065(2) 0.041(2) 0.073(3) 0.002(2) 0.006(2) -0.0222(19) C5 0.078(3) 0.038(2) 0.060(3) 0.0105(19) 0.008(2) -0.008(2) C6 0.051(2) 0.043(2) 0.0398(19) 0.0023(16) -0.0004(17) -0.0051(17) C7 0.0415(17) 0.0427(19) 0.0408(18) 0.0093(15) -0.0075(14) -0.0043(14) C8 0.0364(17) 0.0337(18) 0.0327(15) 0.0081(13) -0.0065(13) 0.0045(14) C9 0.0445(19) 0.0373(19) 0.0317(17) 0.0072(15) 0.0004(15) 0.0013(16) C10 0.052(2) 0.049(2) 0.0367(18) 0.0110(17) 0.0044(16) 0.0036(18) C11 0.057(2) 0.061(2) 0.0343(17) 0.0009(17) -0.0077(17) 0.0139(19) C12 0.063(2) 0.044(2) 0.0405(18) -0.0013(16) -0.0159(17) -0.0003(18) C13 0.051(2) 0.0283(17) 0.0415(18) 0.0059(14) -0.0039(15) -0.0059(14) C14 0.050(2) 0.047(2) 0.050(2) 0.0111(16) -0.0149(18) -0.0074(17) C15 0.052(2) 0.068(3) 0.067(3) 0.013(2) 0.005(2) -0.020(2) C16 0.079(3) 0.060(3) 0.051(2) 0.0160(19) 0.005(2) -0.022(2) C17 0.074(3) 0.048(2) 0.053(2) 0.0171(18) -0.013(2) -0.010(2) C18 0.047(2) 0.035(2) 0.062(2) 0.0101(17) -0.0090(18) -0.0006(16) C19 0.141(4) 0.035(2) 0.072(3) -0.015(2) 0.012(3) 0.008(2) C20 0.045(2) 0.046(3) 0.037(2) -0.0037(14) 0.0008(17) -0.0037(15) C21 0.0427(18) 0.0256(17) 0.0313(17) 0.0060(13) -0.0002(14) 0.0000(13) C22 0.0379(17) 0.0385(19) 0.0304(15) 0.0067(14) 0.0045(14) 0.0026(15) C23 0.0359(16) 0.0323(17) 0.0341(15) 0.0055(13) 0.0011(13) -0.0034(13) C24 0.0422(18) 0.049(2) 0.0438(18) 0.0061(15) 0.0036(14) 0.0108(15) C25 0.0400(17) 0.0389(19) 0.0430(18) -0.0055(15) -0.0062(15) -0.0062(14) C26 0.0382(17) 0.047(2) 0.0426(18) -0.0078(16) 0.0002(15) -0.0097(16) C27 0.050(2) 0.056(2) 0.056(2) -0.004(2) -0.0080(19) -0.0161(19) C28 0.071(3) 0.044(3) 0.070(3) -0.009(2) -0.016(2) -0.016(2) C29 0.074(3) 0.047(2) 0.063(3) -0.024(2) -0.001(2) -0.005(2) C30 0.064(2) 0.050(3) 0.045(2) -0.0140(18) 0.0001(18) -0.0058(19) C31 0.0372(17) 0.0464(19) 0.0395(18) -0.0073(15) 0.0085(14) -0.0030(15) C32 0.0345(16) 0.0356(18) 0.0322(15) -0.0027(14) 0.0023(13) 0.0041(14) C33 0.049(2) 0.0368(19) 0.0341(17) -0.0024(16) 0.0012(14) 0.0072(16) C34 0.057(2) 0.046(2) 0.0330(18) -0.0049(15) -0.0045(16) 0.0096(18) C35 0.066(2) 0.055(2) 0.0309(16) 0.0026(17) 0.0057(17) 0.0076(19) C36 0.059(2) 0.051(2) 0.045(2) 0.0008(17) 0.0237(19) -0.0047(19) C37 0.0440(18) 0.0270(17) 0.0392(17) 0.0018(13) -0.0059(14) -0.0052(14) C38 0.047(2) 0.044(2) 0.0430(19) -0.0002(15) -0.0015(16) -0.0048(15) C39 0.049(2) 0.051(2) 0.064(2) 0.0044(18) -0.0160(19) -0.0068(17) C40 0.076(3) 0.053(2) 0.039(2) -0.0010(17) -0.018(2) -0.017(2) C41 0.088(3) 0.046(2) 0.040(2) -0.0100(18) 0.018(2) -0.008(2) C42 0.043(2) 0.042(2) 0.053(2) -0.0003(17) 0.0030(17) 0.0007(16) C43 0.082(6) 0.041(3) 0.057(4) 0.004(3) -0.024(4) 0.005(5) C43' 0.082(6) 0.041(3) 0.057(4) 0.004(3) -0.024(4) 0.005(5) C44 0.056(2) 0.038(2) 0.037(2) -0.0014(14) -0.0025(17) -0.0020(15) C45 0.0369(18) 0.042(2) 0.0309(16) 0.0009(14) 0.0005(14) -0.0025(14) C46 0.0480(19) 0.039(2) 0.0385(18) -0.0033(16) 0.0087(16) -0.0016(16) C47 0.0391(16) 0.0313(17) 0.0330(15) -0.0103(13) -0.0013(13) 0.0022(14) C48 0.045(2) 0.056(2) 0.051(2) -0.0050(17) -0.0050(16) 0.0092(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 O1 C2 1.397(4) . ? O1 C7 1.404(4) . ? O2 C22 1.205(3) . ? O3 C20 1.242(4) . ? O4 C26 1.388(4) . ? O4 C31 1.403(4) . ? O5 C46 1.188(4) . ? O6 C44 1.206(4) . ? N1 C46 1.372(4) . ? N1 C25 1.403(4) . ? N1 C47 1.506(4) . ? N2 C44 1.360(4) . ? N2 C37 1.431(4) . ? N2 C43 1.502(11) . ? N2 C43' 1.564(16) . ? N3 C22 1.369(4) . ? N3 C1 1.398(4) . ? N3 C23 1.502(4) . ? N4 C20 1.346(4) . ? N4 C13 1.443(4) . ? N4 C19 1.490(5) . ? C1 C2 1.391(4) . ? C1 C6 1.392(4) . ? C2 C3 1.379(5) . ? C3 C4 1.367(6) . ? C3 H3 0.95(5) . ? C4 C5 1.377(6) . ? C4 H4 0.90(3) . ? C5 C6 1.374(5) . ? C5 H5 0.97(4) . ? C6 H6 0.92(3) . ? C7 C12 1.390(4) . ? C7 C8 1.402(4) . ? C8 C9 1.384(4) . ? C8 C23 1.511(4) . ? C9 C10 1.383(5) . ? C9 H9 0.89(3) . ? C10 C11 1.370(5) . ? C10 H10 0.92(4) . ? C11 C12 1.389(5) . ? C11 H11 0.99(3) . ? C12 H12 1.00(4) . ? C13 C18 1.376(4) . ? C13 C14 1.384(5) . ? C14 C15 1.382(5) . ? C14 H14 0.90(4) . ? C15 C16 1.376(5) . ? C15 H15 0.87(5) . ? C16 C17 1.370(6) . ? C16 H16 1.01(3) . ? C17 C18 1.379(5) . ? C17 H17 1.12(4) . ? C18 H18 0.94(3) . ? C20 C21 1.528(4) . ? C21 C22 1.522(4) . ? C21 C23 1.578(4) . ? C21 H21 1.05(4) . ? C23 C24 1.515(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.391(4) . ? C25 C30 1.411(5) . ? C26 C27 1.386(5) . ? C27 C28 1.403(6) . ? C27 H27 1.05(4) . ? C28 C29 1.367(6) . ? C28 H28 1.04(4) . ? C29 C30 1.383(5) . ? C29 H29 1.01(3) . ? C30 H30 0.99(3) . ? C31 C36 1.370(5) . ? C31 C32 1.379(4) . ? C32 C33 1.385(4) . ? C32 C47 1.520(4) . ? C33 C34 1.394(4) . ? C33 H33 1.04(4) . ? C34 C35 1.371(5) . ? C34 H34 1.00(3) . ? C35 C36 1.364(5) . ? C35 H35 0.96(3) . ? C36 H36 0.87(4) . ? C37 C42 1.375(5) . ? C37 C38 1.378(5) . ? C38 C39 1.375(4) . ? C38 H38 1.02(3) . ? C39 C40 1.354(5) . ? C39 H39 1.02(3) . ? C40 C41 1.377(6) . ? C40 H40 0.97(4) . ? C41 C42 1.382(5) . ? C41 H41 0.75(3) . ? C42 H42 0.93(3) . ? C43 C43' 0.665(15) . ? C44 C45 1.510(5) . ? C45 C46 1.530(5) . ? C45 C47 1.575(4) . ? C45 H45 0.99(3) . ? C47 C48 1.525(4) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C7 118.1(2) . . ? C26 O4 C31 116.1(2) . . ? C46 N1 C25 130.8(3) . . ? C46 N1 C47 95.0(2) . . ? C25 N1 C47 131.3(2) . . ? C44 N2 C37 125.0(3) . . ? C44 N2 C43 116.8(5) . . ? C37 N2 C43 117.5(4) . . ? C44 N2 C43' 116.8(6) . . ? C37 N2 C43' 115.7(6) . . ? C43 N2 C43' 24.9(6) . . ? C22 N3 C1 132.8(3) . . ? C22 N3 C23 94.8(2) . . ? C1 N3 C23 131.2(2) . . ? C20 N4 C13 123.5(3) . . ? C20 N4 C19 119.4(3) . . ? C13 N4 C19 117.1(3) . . ? C2 C1 C6 118.4(3) . . ? C2 C1 N3 121.5(3) . . ? C6 C1 N3 120.1(3) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 O1 117.4(3) . . ? C1 C2 O1 122.7(3) . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3 127(3) . . ? C2 C3 H3 112(3) . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 118.9(19) . . ? C5 C4 H4 121.7(19) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 115(3) . . ? C4 C5 H5 124(3) . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6 119.7(18) . . ? C1 C6 H6 119.2(18) . . ? C12 C7 C8 121.6(3) . . ? C12 C7 O1 117.5(3) . . ? C8 C7 O1 120.7(3) . . ? C9 C8 C7 117.0(3) . . ? C9 C8 C23 125.0(3) . . ? C7 C8 C23 118.0(3) . . ? C10 C9 C8 121.9(3) . . ? C10 C9 H9 119.8(18) . . ? C8 C9 H9 117.8(18) . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 123(2) . . ? C9 C10 H10 117(2) . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 115.9(18) . . ? C12 C11 H11 124.3(18) . . ? C11 C12 C7 119.5(3) . . ? C11 C12 H12 128(2) . . ? C7 C12 H12 112(2) . . ? C18 C13 C14 120.5(3) . . ? C18 C13 N4 119.6(3) . . ? C14 C13 N4 119.9(3) . . ? C15 C14 C13 118.7(3) . . ? C15 C14 H14 124(2) . . ? C13 C14 H14 117(2) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 118(4) . . ? C14 C15 H15 117(4) . . ? C17 C16 C15 119.9(4) . . ? C17 C16 H16 116.8(18) . . ? C15 C16 H16 123.3(18) . . ? C16 C17 C18 120.0(4) . . ? C16 C17 H17 127(2) . . ? C18 C17 H17 113(2) . . ? C13 C18 C17 119.9(3) . . ? C13 C18 H18 114(2) . . ? C17 C18 H18 125(2) . . ? O3 C20 N4 122.8(3) . . ? O3 C20 C21 119.8(3) . . ? N4 C20 C21 117.3(3) . . ? C22 C21 C20 113.9(3) . . ? C22 C21 C23 86.1(2) . . ? C20 C21 C23 117.4(3) . . ? C22 C21 H21 107.2(19) . . ? C20 C21 H21 117.6(19) . . ? C23 C21 H21 110.0(19) . . ? O2 C22 N3 131.5(3) . . ? O2 C22 C21 135.2(3) . . ? N3 C22 C21 93.1(2) . . ? N3 C23 C8 109.9(2) . . ? N3 C23 C24 115.4(2) . . ? C8 C23 C24 112.1(2) . . ? N3 C23 C21 86.0(2) . . ? C8 C23 C21 115.5(2) . . ? C24 C23 C21 115.5(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N1 121.6(3) . . ? C26 C25 C30 118.6(3) . . ? N1 C25 C30 119.8(3) . . ? C27 C26 O4 117.1(3) . . ? C27 C26 C25 121.6(3) . . ? O4 C26 C25 121.2(3) . . ? C26 C27 C28 118.9(4) . . ? C26 C27 H27 117.7(19) . . ? C28 C27 H27 123.1(19) . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28 123(2) . . ? C27 C28 H28 117(2) . . ? C28 C29 C30 121.9(4) . . ? C28 C29 H29 120.5(19) . . ? C30 C29 H29 117.6(19) . . ? C29 C30 C25 119.2(4) . . ? C29 C30 H30 122.5(18) . . ? C25 C30 H30 118.3(18) . . ? C36 C31 C32 121.3(3) . . ? C36 C31 O4 118.8(3) . . ? C32 C31 O4 119.8(3) . . ? C31 C32 C33 118.1(3) . . ? C31 C32 C47 118.8(3) . . ? C33 C32 C47 123.1(3) . . ? C32 C33 C34 120.6(3) . . ? C32 C33 H33 119.3(19) . . ? C34 C33 H33 120(2) . . ? C35 C34 C33 119.5(3) . . ? C35 C34 H34 121.9(18) . . ? C33 C34 H34 118.5(18) . . ? C36 C35 C34 120.3(3) . . ? C36 C35 H35 120.4(18) . . ? C34 C35 H35 119.2(18) . . ? C35 C36 C31 120.2(4) . . ? C35 C36 H36 119(2) . . ? C31 C36 H36 120(2) . . ? C42 C37 C38 120.2(3) . . ? C42 C37 N2 119.7(3) . . ? C38 C37 N2 120.1(3) . . ? C39 C38 C37 119.4(3) . . ? C39 C38 H38 121.8(17) . . ? C37 C38 H38 118.8(17) . . ? C40 C39 C38 121.0(3) . . ? C40 C39 H39 119.8(16) . . ? C38 C39 H39 119.2(16) . . ? C39 C40 C41 119.9(3) . . ? C39 C40 H40 113(2) . . ? C41 C40 H40 127(2) . . ? C40 C41 C42 120.1(4) . . ? C40 C41 H41 128(3) . . ? C42 C41 H41 112(3) . . ? C37 C42 C41 119.4(3) . . ? C37 C42 H42 122.6(18) . . ? C41 C42 H42 117.9(18) . . ? C43' C43 N2 83(2) . . ? C43 C43' N2 72(2) . . ? O6 C44 N2 121.6(3) . . ? O6 C44 C45 121.1(3) . . ? N2 C44 C45 117.2(3) . . ? C44 C45 C46 115.0(3) . . ? C44 C45 C47 118.6(3) . . ? C46 C45 C47 86.3(2) . . ? C44 C45 H45 112.9(15) . . ? C46 C45 H45 106.5(15) . . ? C47 C45 H45 114.2(15) . . ? O5 C46 N1 131.4(3) . . ? O5 C46 C45 135.8(3) . . ? N1 C46 C45 92.7(2) . . ? N1 C47 C32 111.0(2) . . ? N1 C47 C48 112.9(2) . . ? C32 C47 C48 112.6(2) . . ? N1 C47 C45 86.0(2) . . ? C32 C47 C45 117.6(2) . . ? C48 C47 C45 114.0(3) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.229 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.041 # Attachment 'compound15.cif.txt' data_compound15 _database_code_depnum_ccdc_archive 'CCDC 804600' #TrackingRef 'compound15.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2 O' _chemical_formula_weight 248.28 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 P2(1)/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 12.294(4) _cell_length_b 4.9467(14) _cell_length_c 20.381(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.322(4) _cell_angle_gamma 90.00 _cell_volume 1215.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2935 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 27.50 _exptl_crystal_description Chunk _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.087 _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 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9078 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2766 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0451P)^2^+0.3060P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2766 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 O1 O 0.13873(8) 0.6596(2) 0.55119(5) 0.0218(3) Uani 1 1 d . . . N1 N 0.32288(10) 0.7557(2) 0.55977(6) 0.0168(3) Uani 1 1 d . . . N2 N 0.42654(11) 0.3506(3) 0.44811(7) 0.0286(3) Uani 1 1 d . . . C1 C 0.03208(12) -0.0992(3) 0.39706(7) 0.0183(3) Uani 1 1 d . . . H1 H -0.0203 -0.0603 0.4244 0.022 Uiso 1 1 calc R . . C2 C 0.01040(13) -0.3045(3) 0.35033(7) 0.0200(3) Uani 1 1 d . . . H2 H -0.0555 -0.4085 0.3466 0.024 Uiso 1 1 calc R . . C3 C 0.08474(13) -0.3588(3) 0.30893(7) 0.0206(3) Uani 1 1 d . . . H3 H 0.0693 -0.4977 0.2762 0.025 Uiso 1 1 calc R . . C4 C 0.18189(13) -0.2093(3) 0.31544(8) 0.0221(3) Uani 1 1 d . . . H4 H 0.2329 -0.2465 0.2871 0.027 Uiso 1 1 calc R . . C5 C 0.20474(13) -0.0065(3) 0.36286(7) 0.0205(3) Uani 1 1 d . . . H5 H 0.2717 0.0936 0.3671 0.025 Uiso 1 1 calc R . . C6 C 0.13011(12) 0.0527(3) 0.40480(7) 0.0162(3) Uani 1 1 d . . . C7 C 0.14578(13) 0.2645(3) 0.45556(7) 0.0160(3) Uani 1 1 d . . . C8 C 0.23623(12) 0.4112(3) 0.48175(7) 0.0156(3) Uani 1 1 d . . . C9 C 0.22788(12) 0.6201(3) 0.53453(7) 0.0161(3) Uani 1 1 d . . . C10 C 0.33845(12) 0.9542(3) 0.61120(7) 0.0162(3) Uani 1 1 d . . . C11 C 0.43351(12) 1.1139(3) 0.61820(7) 0.0192(3) Uani 1 1 d . . . H11 H 0.4836 1.0897 0.5886 0.023 Uiso 1 1 calc R . . C12 C 0.45532(13) 1.3082(3) 0.66821(8) 0.0223(3) Uani 1 1 d . . . H12 H 0.5203 1.4159 0.6728 0.027 Uiso 1 1 calc R . . C13 C 0.38275(13) 1.3454(3) 0.71138(8) 0.0221(4) Uani 1 1 d . . . H13 H 0.3977 1.4778 0.7457 0.027 Uiso 1 1 calc R . . C14 C 0.28804(13) 1.1875(3) 0.70400(7) 0.0215(3) Uani 1 1 d . . . H14 H 0.2378 1.2140 0.7334 0.026 Uiso 1 1 calc R . . C15 C 0.26519(13) 0.9911(3) 0.65442(7) 0.0188(3) Uani 1 1 d . . . H15 H 0.2002 0.8833 0.6501 0.023 Uiso 1 1 calc R . . C16 C 0.34102(13) 0.3754(3) 0.46216(7) 0.0190(3) Uani 1 1 d . . . H1N H 0.3854(16) 0.709(3) 0.5458(8) 0.027(5) Uiso 1 1 d . . . H7 H 0.0806(14) 0.304(3) 0.4745(8) 0.021(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0155(6) 0.0275(6) 0.0235(6) -0.0070(5) 0.0067(5) 0.0006(4) N1 0.0131(6) 0.0198(6) 0.0179(6) -0.0045(5) 0.0041(5) 0.0012(5) N2 0.0182(7) 0.0373(8) 0.0317(8) -0.0148(7) 0.0081(6) -0.0019(6) C1 0.0161(7) 0.0209(8) 0.0181(7) 0.0024(6) 0.0038(6) 0.0024(6) C2 0.0174(7) 0.0200(8) 0.0213(8) 0.0019(6) 0.0001(6) -0.0006(6) C3 0.0245(8) 0.0179(7) 0.0179(8) -0.0030(6) 0.0002(6) 0.0003(6) C4 0.0244(8) 0.0230(8) 0.0203(8) -0.0028(6) 0.0076(7) -0.0001(7) C5 0.0184(8) 0.0226(8) 0.0216(8) -0.0013(6) 0.0069(6) -0.0040(6) C6 0.0177(8) 0.0159(7) 0.0150(7) 0.0031(6) 0.0035(6) 0.0024(6) C7 0.0162(7) 0.0173(7) 0.0153(7) 0.0017(6) 0.0047(6) 0.0016(6) C8 0.0154(7) 0.0175(7) 0.0144(7) 0.0020(6) 0.0042(6) 0.0032(6) C9 0.0171(7) 0.0164(7) 0.0146(7) 0.0021(6) 0.0028(6) 0.0022(6) C10 0.0178(7) 0.0152(7) 0.0139(7) 0.0019(6) -0.0011(6) 0.0031(6) C11 0.0176(7) 0.0192(7) 0.0206(8) 0.0011(6) 0.0033(6) 0.0020(6) C12 0.0197(8) 0.0188(8) 0.0259(8) 0.0004(7) -0.0018(6) -0.0012(6) C13 0.0274(9) 0.0186(8) 0.0185(8) -0.0031(6) 0.0002(7) 0.0029(6) C14 0.0239(8) 0.0244(8) 0.0166(7) -0.0016(6) 0.0052(6) 0.0036(7) C15 0.0188(8) 0.0206(8) 0.0169(7) -0.0004(6) 0.0033(6) -0.0009(6) C16 0.0199(8) 0.0205(8) 0.0166(7) -0.0057(6) 0.0032(6) 0.0005(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 O1 C9 1.2251(17) . ? N1 C9 1.3575(19) . ? N1 C10 1.4215(19) . ? N1 H1N 0.899(18) . ? N2 C16 1.149(2) . ? C1 C2 1.382(2) . ? C1 C6 1.403(2) . ? C1 H1 0.9500 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.389(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C4 H4 0.9500 . ? C5 C6 1.402(2) . ? C5 H5 0.9500 . ? C6 C7 1.459(2) . ? C7 C8 1.347(2) . ? C7 H7 0.975(16) . ? C8 C16 1.433(2) . ? C8 C9 1.510(2) . ? C10 C15 1.390(2) . ? C10 C11 1.395(2) . ? C11 C12 1.388(2) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 C15 1.390(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 N1 C10 127.01(13) . . ? C9 N1 H1N 118.7(11) . . ? C10 N1 H1N 114.1(11) . . ? C2 C1 C6 121.09(14) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C1 C2 C3 120.05(14) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 119.73(14) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.39(14) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.67(14) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 118.05(13) . . ? C5 C6 C7 124.84(13) . . ? C1 C6 C7 117.10(13) . . ? C8 C7 C6 130.68(14) . . ? C8 C7 H7 114.5(10) . . ? C6 C7 H7 114.8(10) . . ? C7 C8 C16 122.71(14) . . ? C7 C8 C9 118.99(13) . . ? C16 C8 C9 118.29(13) . . ? O1 C9 N1 124.48(14) . . ? O1 C9 C8 119.76(13) . . ? N1 C9 C8 115.75(13) . . ? C15 C10 C11 119.67(14) . . ? C15 C10 N1 123.22(14) . . ? C11 C10 N1 117.10(14) . . ? C12 C11 C10 120.29(15) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.24(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.30(14) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 121.23(15) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C10 C15 C14 119.26(14) . . ? C10 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? N2 C16 C8 177.99(16) . . ? 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 -1.7(2) . . . . ? C1 C2 C3 C4 1.1(2) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 C1 -0.1(2) . . . . ? C4 C5 C6 C7 -179.07(14) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? C2 C1 C6 C7 -179.81(13) . . . . ? C5 C6 C7 C8 -13.0(3) . . . . ? C1 C6 C7 C8 168.00(15) . . . . ? C6 C7 C8 C16 -0.7(3) . . . . ? C6 C7 C8 C9 -179.98(14) . . . . ? C10 N1 C9 O1 3.3(2) . . . . ? C10 N1 C9 C8 -177.63(12) . . . . ? C7 C8 C9 O1 -2.4(2) . . . . ? C16 C8 C9 O1 178.33(13) . . . . ? C7 C8 C9 N1 178.51(13) . . . . ? C16 C8 C9 N1 -0.78(19) . . . . ? C9 N1 C10 C15 16.3(2) . . . . ? C9 N1 C10 C11 -164.77(14) . . . . ? C15 C10 C11 C12 0.3(2) . . . . ? N1 C10 C11 C12 -178.69(13) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C11 C10 C15 C14 0.1(2) . . . . ? N1 C10 C15 C14 178.97(13) . . . . ? C13 C14 C15 C10 -0.5(2) . . . . ? C7 C8 C16 N2 -163(5) . . . . ? C9 C8 C16 N2 16(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.239 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.044