# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'A. K. Sahoo' _publ_contact_author_email akssc@uohyd.ernet.in loop_ _publ_author_name 'M. Bhanuchandra' 'M. R. Kuram' 'A. K. Sahoo' data_aks29 _database_code_depnum_ccdc_archive 'CCDC 863901' #TrackingRef '- aks29.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N2 O' _chemical_formula_sum 'C22 H18 N2 O' _chemical_formula_weight 326.38 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 19.7487(16) _cell_length_b 9.7599(8) _cell_length_c 18.4670(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3559.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9821 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10966 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 29.15 _reflns_number_total 6639 _reflns_number_gt 3376 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _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^)+(0.0343P)^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 SHELXL _refine_ls_extinction_coef 0.0018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.9(17) _refine_ls_number_reflns 6639 _refine_ls_number_parameters 460 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 N1 N 0.18435(15) 1.1047(3) 0.14386(14) 0.0744(8) Uani 1 1 d . . . C1 C 0.08787(15) 0.7229(4) 0.07460(15) 0.0650(9) Uani 1 1 d . . . O1 O 0.18201(12) 0.8601(3) 0.04803(12) 0.1114(10) Uani 1 1 d . . . N3 N 0.85408(15) 0.4365(3) 0.25893(15) 0.0830(8) Uani 1 1 d . . . C22 C 0.22649(19) 1.1887(4) 0.10503(15) 0.0710(9) Uani 1 1 d . . . C31 C 0.80378(19) 0.5435(4) 0.27125(19) 0.0782(10) Uani 1 1 d . . . C10 C 0.22089(16) 1.0023(4) 0.26039(17) 0.0688(9) Uani 1 1 d . . . C7 C 0.14220(17) 0.8204(4) 0.09322(16) 0.0736(9) Uani 1 1 d . . . C43 C 0.8202(2) 0.3446(5) 0.1390(2) 0.0957(12) Uani 1 1 d . . . H43 H 0.7825 0.4003 0.1326 0.115 Uiso 1 1 calc R . . C15 C 0.17959(19) 1.0800(5) 0.30319(19) 0.0991(14) Uani 1 1 d . . . H15 H 0.1423 1.1240 0.2832 0.119 Uiso 1 1 calc R . . C29 C 0.8903(2) 0.7290(4) 0.2955(2) 0.0928(12) Uani 1 1 d . . . C23 C 0.92991(17) 0.8162(4) 0.3451(2) 0.0806(10) Uani 1 1 d . . . C8 C 0.14963(17) 0.8697(4) 0.17064(15) 0.0744(10) Uani 1 1 d . . . H8A H 0.1603 0.7918 0.2012 0.089 Uiso 1 1 calc R . . H8B H 0.1066 0.9066 0.1867 0.089 Uiso 1 1 calc R . . N2 N 0.12037(16) 1.1540(4) 0.14495(17) 0.0982(10) Uani 1 1 d . . . C9 C 0.20428(18) 0.9789(4) 0.18075(16) 0.0695(9) Uani 1 1 d . . . C37 C 0.7333(2) 0.3828(4) 0.3469(2) 0.0927(11) Uani 1 1 d . . . H37 H 0.7731 0.3467 0.3661 0.111 Uiso 1 1 calc R . . C39 C 0.9171(2) 0.2731(5) 0.2109(3) 0.1007(13) Uani 1 1 d . . . C6 C 0.0830(2) 0.6767(4) 0.00437(18) 0.0859(11) Uani 1 1 d . . . H6 H 0.1133 0.7092 -0.0302 0.103 Uiso 1 1 calc R . . C30 C 0.83060(18) 0.6492(4) 0.32365(18) 0.0872(11) Uani 1 1 d . . . H30A H 0.7945 0.7128 0.3353 0.105 Uiso 1 1 calc R . . H30B H 0.8437 0.6035 0.3681 0.105 Uiso 1 1 calc R . . C2 C 0.04203(18) 0.6733(4) 0.12402(18) 0.0842(11) Uani 1 1 d . . . H2 H 0.0440 0.7033 0.1718 0.101 Uiso 1 1 calc R . . C44 C 0.86005(19) 0.3535(4) 0.2001(2) 0.0781(10) Uani 1 1 d . . . C5 C 0.0345(2) 0.5838(5) -0.0156(2) 0.1000(13) Uani 1 1 d . . . H5 H 0.0320 0.5543 -0.0634 0.120 Uiso 1 1 calc R . . C11 C 0.27774(19) 0.9468(4) 0.28958(18) 0.0867(11) Uani 1 1 d . . . H11 H 0.3071 0.8970 0.2603 0.104 Uiso 1 1 calc R . . C36 C 0.6717(3) 0.3332(6) 0.3699(2) 0.1217(17) Uani 1 1 d . . . H36 H 0.6701 0.2628 0.4038 0.146 Uiso 1 1 calc R . . C14 C 0.1934(2) 1.0934(6) 0.3771(2) 0.1133(16) Uani 1 1 d . . . H14 H 0.1646 1.1437 0.4066 0.136 Uiso 1 1 calc R . . C17 C 0.1870(3) 1.2954(5) 0.0785(2) 0.0913(12) Uani 1 1 d . . . C32 C 0.7366(2) 0.4847(4) 0.29620(18) 0.0790(10) Uani 1 1 d . . . C18 C 0.2163(4) 1.3961(6) 0.0335(3) 0.1248(18) Uani 1 1 d . . . H18 H 0.1905 1.4673 0.0145 0.150 Uiso 1 1 calc R . . C4 C -0.0104(2) 0.5338(5) 0.0347(2) 0.0993(13) Uani 1 1 d . . . H4 H -0.0428 0.4694 0.0213 0.119 Uiso 1 1 calc R . . O2 O 0.90394(17) 0.7253(4) 0.23176(15) 0.1433(13) Uani 1 1 d . . . C3 C -0.0072(2) 0.5789(5) 0.1039(2) 0.1007(13) Uani 1 1 d . . . H3 H -0.0379 0.5467 0.1380 0.121 Uiso 1 1 calc R . . C21 C 0.2954(2) 1.1812(4) 0.09127(17) 0.0849(11) Uani 1 1 d . . . H21 H 0.3220 1.1118 0.1109 0.102 Uiso 1 1 calc R . . C33 C 0.6775(3) 0.5354(5) 0.2687(2) 0.1153(15) Uani 1 1 d . . . H33 H 0.6787 0.6026 0.2330 0.138 Uiso 1 1 calc R . . C28 C 0.9755(2) 0.9066(6) 0.3161(3) 0.1261(17) Uani 1 1 d . . . H28 H 0.9824 0.9087 0.2663 0.151 Uiso 1 1 calc R . . C13 C 0.2488(3) 1.0331(6) 0.4052(2) 0.1127(15) Uani 1 1 d . . . H13 H 0.2573 1.0393 0.4546 0.135 Uiso 1 1 calc R . . N4 N 0.9036(2) 0.4130(5) 0.30750(18) 0.1207(13) Uani 1 1 d . . . C24 C 0.9213(2) 0.8178(5) 0.4183(2) 0.1057(14) Uani 1 1 d . . . H24 H 0.8907 0.7575 0.4394 0.127 Uiso 1 1 calc R . . C38 C 0.9412(2) 0.3167(6) 0.2789(4) 0.1355(18) Uani 1 1 d . . . H38 H 0.9796 0.2809 0.3011 0.163 Uiso 1 1 calc R . . C12 C 0.2924(2) 0.9630(5) 0.3618(2) 0.1062(13) Uani 1 1 d . . . H12 H 0.3320 0.9263 0.3809 0.127 Uiso 1 1 calc R . . C20 C 0.3224(3) 1.2799(6) 0.0477(2) 0.1174(16) Uani 1 1 d . . . H20 H 0.3684 1.2774 0.0368 0.141 Uiso 1 1 calc R . . C19 C 0.2821(5) 1.3852(7) 0.0191(3) 0.142(3) Uani 1 1 d . . . H19 H 0.3022 1.4499 -0.0110 0.170 Uiso 1 1 calc R . . C16 C 0.1225(3) 1.2672(6) 0.1054(2) 0.1116(15) Uani 1 1 d . . . H16 H 0.0849 1.3221 0.0965 0.134 Uiso 1 1 calc R . . C35 C 0.6135(4) 0.3862(8) 0.3436(4) 0.139(2) Uani 1 1 d . . . H35 H 0.5720 0.3533 0.3597 0.166 Uiso 1 1 calc R . . C41 C 0.8959(5) 0.1698(7) 0.0986(4) 0.155(3) Uani 1 1 d . . . H41 H 0.9072 0.1066 0.0629 0.186 Uiso 1 1 calc R . . C26 C 1.0024(3) 0.9937(6) 0.4329(4) 0.145(2) Uani 1 1 d . . . H26 H 1.0273 1.0520 0.4626 0.175 Uiso 1 1 calc R . . C40 C 0.9362(3) 0.1784(6) 0.1577(5) 0.147(2) Uani 1 1 d . . . H40 H 0.9747 0.1242 0.1628 0.176 Uiso 1 1 calc R . . C34 C 0.6159(3) 0.4876(8) 0.2935(4) 0.149(2) Uani 1 1 d . . . H34 H 0.5759 0.5252 0.2758 0.178 Uiso 1 1 calc R . . C25 C 0.9570(3) 0.9068(7) 0.4614(3) 0.1352(19) Uani 1 1 d . . . H25 H 0.9496 0.9068 0.5111 0.162 Uiso 1 1 calc R . . C42 C 0.8389(4) 0.2497(7) 0.0884(3) 0.138(2) Uani 1 1 d . . . H42 H 0.8131 0.2388 0.0467 0.165 Uiso 1 1 calc R . . C27 C 1.0113(3) 0.9952(7) 0.3606(4) 0.156(2) Uani 1 1 d . . . H27 H 1.0419 1.0566 0.3403 0.187 Uiso 1 1 calc R . . H9 H 0.2470(16) 0.945(3) 0.1575(14) 0.073(9) Uiso 1 1 d . . . H31 H 0.7975(14) 0.588(3) 0.2219(17) 0.086(10) 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 N1 0.074(2) 0.077(2) 0.0728(16) 0.0052(17) -0.0050(14) -0.0002(19) C1 0.0633(19) 0.072(2) 0.0597(19) 0.0000(17) 0.0049(15) -0.0003(19) O1 0.1066(18) 0.158(3) 0.0693(14) -0.0085(15) 0.0223(13) -0.0521(19) N3 0.087(2) 0.084(2) 0.0772(18) 0.0022(19) -0.0037(16) 0.0182(19) C22 0.091(3) 0.066(2) 0.0559(18) -0.0040(18) -0.0143(17) -0.008(2) C31 0.099(3) 0.070(3) 0.066(2) 0.004(2) -0.0004(19) 0.015(2) C10 0.070(2) 0.072(2) 0.0638(19) 0.0069(19) -0.0006(16) -0.008(2) C7 0.075(2) 0.085(3) 0.0612(19) 0.007(2) 0.0085(16) -0.003(2) C43 0.124(3) 0.094(3) 0.069(2) 0.002(2) 0.022(2) -0.014(3) C15 0.081(2) 0.136(4) 0.080(3) -0.015(3) 0.0024(18) 0.001(3) C29 0.107(3) 0.092(3) 0.080(3) 0.007(2) 0.034(2) 0.009(3) C23 0.067(2) 0.078(3) 0.097(3) 0.023(2) 0.0179(19) 0.007(2) C8 0.079(2) 0.079(3) 0.0654(19) 0.0011(19) 0.0102(15) -0.005(2) N2 0.076(2) 0.110(3) 0.109(2) -0.001(2) -0.0200(17) 0.009(2) C9 0.070(2) 0.074(3) 0.064(2) 0.0048(19) 0.0055(16) 0.000(2) C37 0.104(3) 0.086(3) 0.088(2) -0.005(3) 0.000(2) 0.004(3) C39 0.087(3) 0.072(3) 0.142(4) -0.003(3) 0.033(3) 0.004(3) C6 0.089(3) 0.094(3) 0.074(2) -0.003(2) 0.0020(16) -0.008(3) C30 0.102(3) 0.082(3) 0.078(2) -0.002(2) 0.0210(19) -0.004(2) C2 0.090(2) 0.092(3) 0.072(2) -0.004(2) 0.0097(18) -0.014(3) C44 0.084(3) 0.072(3) 0.078(2) 0.004(2) 0.027(2) -0.003(2) C5 0.102(3) 0.113(4) 0.085(2) -0.014(3) -0.010(2) -0.008(3) C11 0.102(3) 0.072(3) 0.086(3) 0.000(2) -0.019(2) 0.006(2) C36 0.134(4) 0.124(5) 0.108(3) -0.019(3) 0.028(3) -0.024(4) C14 0.090(3) 0.165(5) 0.085(3) -0.027(3) 0.013(2) -0.023(3) C17 0.122(4) 0.074(3) 0.078(2) -0.004(2) -0.028(2) 0.000(3) C32 0.093(3) 0.068(3) 0.076(2) -0.007(2) -0.0047(19) 0.017(2) C18 0.206(6) 0.074(4) 0.095(3) 0.002(3) -0.042(4) -0.009(5) C4 0.094(3) 0.095(3) 0.109(3) -0.018(3) -0.009(2) -0.009(3) O2 0.178(3) 0.158(3) 0.0936(19) -0.005(2) 0.0504(19) -0.031(3) C3 0.094(3) 0.099(3) 0.110(3) -0.003(3) 0.022(2) -0.024(3) C21 0.097(3) 0.080(3) 0.077(2) -0.002(2) 0.0043(19) -0.019(3) C33 0.109(4) 0.111(4) 0.126(3) 0.009(3) -0.021(3) 0.026(3) C28 0.097(3) 0.138(5) 0.143(4) 0.020(4) 0.033(3) -0.009(4) C13 0.125(4) 0.136(5) 0.077(3) 0.005(3) -0.009(3) -0.025(4) N4 0.120(3) 0.119(4) 0.123(3) -0.009(3) -0.039(2) 0.036(3) C24 0.091(3) 0.124(4) 0.102(3) 0.021(3) -0.001(2) -0.032(3) C38 0.098(3) 0.116(5) 0.193(5) 0.004(4) -0.025(3) 0.033(3) C12 0.120(3) 0.092(3) 0.107(3) 0.012(3) -0.038(3) -0.008(3) C20 0.139(4) 0.116(4) 0.097(3) -0.001(3) 0.014(3) -0.053(4) C19 0.240(8) 0.082(4) 0.103(4) 0.006(3) -0.009(5) -0.057(6) C16 0.122(4) 0.099(4) 0.114(3) -0.010(3) -0.042(3) 0.038(3) C35 0.119(5) 0.134(6) 0.163(5) -0.067(4) 0.032(4) -0.026(5) C41 0.185(7) 0.114(5) 0.166(6) -0.037(5) 0.102(5) -0.035(6) C26 0.112(4) 0.137(5) 0.187(6) 0.055(5) -0.034(4) -0.045(4) C40 0.119(5) 0.093(4) 0.229(7) -0.005(5) 0.084(5) 0.005(4) C34 0.091(4) 0.157(6) 0.198(6) -0.036(5) -0.026(4) 0.021(4) C25 0.139(4) 0.153(5) 0.114(4) 0.022(4) -0.018(3) -0.042(4) C42 0.179(6) 0.139(5) 0.094(3) -0.024(4) 0.047(3) -0.038(5) C27 0.101(4) 0.154(6) 0.213(7) 0.071(6) 0.022(4) -0.034(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 N1 N2 1.352(4) . ? N1 C22 1.371(4) . ? N1 C9 1.458(4) . ? C1 C2 1.374(4) . ? C1 C6 1.377(4) . ? C1 C7 1.475(4) . ? O1 C7 1.210(3) . ? N3 N4 1.347(4) . ? N3 C44 1.360(4) . ? N3 C31 1.459(4) . ? C22 C21 1.386(5) . ? C22 C17 1.390(5) . ? C31 C30 1.511(5) . ? C31 C32 1.517(5) . ? C10 C11 1.358(4) . ? C10 C15 1.366(5) . ? C10 C9 1.524(4) . ? C7 C8 1.515(4) . ? C43 C42 1.368(6) . ? C43 C44 1.378(5) . ? C15 C14 1.397(5) . ? C29 O2 1.209(4) . ? C29 C23 1.475(5) . ? C29 C30 1.505(5) . ? C23 C24 1.362(5) . ? C23 C28 1.369(5) . ? C8 C9 1.528(4) . ? N2 C16 1.325(5) . ? C37 C32 1.368(5) . ? C37 C36 1.376(5) . ? C39 C44 1.388(5) . ? C39 C40 1.400(7) . ? C39 C38 1.409(7) . ? C6 C5 1.370(5) . ? C2 C3 1.390(5) . ? C5 C4 1.374(5) . ? C11 C12 1.373(4) . ? C36 C35 1.351(7) . ? C14 C13 1.346(5) . ? C17 C16 1.395(6) . ? C17 C18 1.411(7) . ? C32 C33 1.367(5) . ? C18 C19 1.332(7) . ? C4 C3 1.353(5) . ? C21 C20 1.364(5) . ? C33 C34 1.380(7) . ? C28 C27 1.387(7) . ? C13 C12 1.362(5) . ? N4 C38 1.308(6) . ? C24 C25 1.373(6) . ? C20 C19 1.403(7) . ? C35 C34 1.355(7) . ? C41 C40 1.354(8) . ? C41 C42 1.382(8) . ? C26 C25 1.342(6) . ? C26 C27 1.346(7) . ? 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 N2 N1 C22 111.2(3) . . ? N2 N1 C9 123.0(3) . . ? C22 N1 C9 125.7(3) . . ? C2 C1 C6 117.7(3) . . ? C2 C1 C7 123.5(3) . . ? C6 C1 C7 118.8(3) . . ? N4 N3 C44 111.6(3) . . ? N4 N3 C31 120.8(3) . . ? C44 N3 C31 127.6(3) . . ? N1 C22 C21 131.3(4) . . ? N1 C22 C17 107.0(3) . . ? C21 C22 C17 121.8(4) . . ? N3 C31 C30 110.5(3) . . ? N3 C31 C32 111.8(3) . . ? C30 C31 C32 111.7(3) . . ? C11 C10 C15 119.0(3) . . ? C11 C10 C9 120.1(3) . . ? C15 C10 C9 120.9(3) . . ? O1 C7 C1 121.2(3) . . ? O1 C7 C8 119.1(3) . . ? C1 C7 C8 119.7(3) . . ? C42 C43 C44 116.7(5) . . ? C10 C15 C14 120.0(4) . . ? O2 C29 C23 120.2(4) . . ? O2 C29 C30 119.7(4) . . ? C23 C29 C30 120.0(3) . . ? C24 C23 C28 117.5(4) . . ? C24 C23 C29 123.8(4) . . ? C28 C23 C29 118.6(4) . . ? C7 C8 C9 113.9(3) . . ? C16 N2 N1 105.0(4) . . ? N1 C9 C10 112.5(3) . . ? N1 C9 C8 109.9(3) . . ? C10 C9 C8 112.0(3) . . ? C32 C37 C36 120.6(4) . . ? C44 C39 C40 119.4(5) . . ? C44 C39 C38 103.4(4) . . ? C40 C39 C38 137.2(6) . . ? C5 C6 C1 121.3(3) . . ? C29 C30 C31 114.0(3) . . ? C1 C2 C3 121.1(3) . . ? N3 C44 C43 129.9(4) . . ? N3 C44 C39 107.0(4) . . ? C43 C44 C39 123.1(4) . . ? C6 C5 C4 120.3(4) . . ? C10 C11 C12 120.9(4) . . ? C35 C36 C37 120.4(5) . . ? C13 C14 C15 119.7(4) . . ? C22 C17 C16 103.8(4) . . ? C22 C17 C18 119.9(5) . . ? C16 C17 C18 136.2(6) . . ? C33 C32 C37 118.5(4) . . ? C33 C32 C31 119.8(4) . . ? C37 C32 C31 121.7(4) . . ? C19 C18 C17 117.5(6) . . ? C3 C4 C5 119.5(4) . . ? C4 C3 C2 120.1(4) . . ? C20 C21 C22 117.1(4) . . ? C32 C33 C34 120.5(5) . . ? C23 C28 C27 120.4(5) . . ? C14 C13 C12 120.4(4) . . ? C38 N4 N3 105.4(4) . . ? C23 C24 C25 121.2(4) . . ? N4 C38 C39 112.6(4) . . ? C13 C12 C11 119.8(4) . . ? C21 C20 C19 121.1(5) . . ? C18 C19 C20 122.5(7) . . ? N2 C16 C17 112.9(4) . . ? C36 C35 C34 119.7(6) . . ? C40 C41 C42 123.7(7) . . ? C25 C26 C27 118.8(6) . . ? C41 C40 C39 116.6(6) . . ? C35 C34 C33 120.3(6) . . ? C26 C25 C24 121.0(5) . . ? C43 C42 C41 120.6(6) . . ? C26 C27 C28 121.0(5) . . ? _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 29.15 _diffrn_measured_fraction_theta_full 0.868 _refine_diff_density_max 0.097 _refine_diff_density_min -0.104 _refine_diff_density_rms 0.021 # Attachment '- aks31.cif' data_aks31 _database_code_depnum_ccdc_archive 'CCDC 863903' #TrackingRef '- aks31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C24 _chemical_formula_sum 'C24 H20 N2 O' _chemical_formula_weight 352.42 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 10.9862(9) _cell_length_b 19.4309(13) _cell_length_c 9.9118(9) _cell_angle_alpha 90.00 _cell_angle_beta 115.173(10) _cell_angle_gamma 90.00 _cell_volume 1914.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3462 _cell_measurement_theta_min 3.0864 _cell_measurement_theta_max 24.6519 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.91047 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7332 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 24.68 _reflns_number_total 3254 _reflns_number_gt 2181 _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^)+(0.0538P)^2^+0.0008P] 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 SHELXL _refine_ls_extinction_coef 0.0139(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3254 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 4.308 _refine_ls_shift/su_mean 0.028 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 N2 N 0.76296(11) 0.04352(6) 0.61955(13) 0.0491(3) Uani 1 1 d . . . N1 N 0.86632(10) 0.00305(6) 0.70657(13) 0.0488(3) Uani 1 1 d . . . O1 O 0.80883(10) 0.04603(6) 0.97736(13) 0.0754(4) Uani 1 1 d . . . C1 C 0.57187(13) 0.04476(7) 0.86696(15) 0.0450(4) Uani 1 1 d . . . C7 C 0.70630(14) 0.01862(8) 0.88876(16) 0.0505(4) Uani 1 1 d . . . C18 C 0.81528(13) 0.08695(7) 0.55386(16) 0.0467(4) Uani 1 1 d . . . C8 C 0.71501(14) -0.04495(7) 0.80530(17) 0.0512(4) Uani 1 1 d . . . H8A H 0.6440 -0.0432 0.7048 0.061 Uiso 1 1 calc R . . H8B H 0.6997 -0.0852 0.8538 0.061 Uiso 1 1 calc R . . C9 C 0.84930(14) -0.05287(7) 0.79688(18) 0.0485(4) Uani 1 1 d . . . H9 H 0.9207(13) -0.0486(7) 0.8982(17) 0.058 Uiso 1 1 calc . . . C20 C 0.60338(15) 0.15532(8) 0.44005(18) 0.0576(4) Uani 1 1 d . . . H20 H 0.5686 0.1301 0.4953 0.069 Uiso 1 1 calc R . . C19 C 0.73153(14) 0.14067(7) 0.45242(16) 0.0504(4) Uani 1 1 d . . . C6 C 0.56452(16) 0.09892(8) 0.95337(19) 0.0623(5) Uani 1 1 d . . . H6 H 0.6433 0.1188 1.0228 0.075 Uiso 1 1 calc R . . C10 C 0.86393(13) -0.12225(8) 0.73647(18) 0.0491(4) Uani 1 1 d . . . C4 C 0.32559(16) 0.09540(9) 0.83593(19) 0.0631(5) Uani 1 1 d . . . H4 H 0.2429 0.1127 0.8249 0.076 Uiso 1 1 calc R . . C2 C 0.45312(14) 0.01665(8) 0.76553(19) 0.0610(5) Uani 1 1 d . . . H2 H 0.4555 -0.0200 0.7062 0.073 Uiso 1 1 calc R . . C16 C 0.97980(15) 0.01987(8) 0.6960(2) 0.0664(5) Uani 1 1 d . . . H16 H 1.0631 -0.0012 0.7458 0.080 Uiso 1 1 calc R . . C17 C 0.95123(15) 0.07338(9) 0.5990(2) 0.0657(5) Uani 1 1 d . . . H17 H 1.0102 0.0961 0.5691 0.079 Uiso 1 1 calc R . . C3 C 0.33083(15) 0.04188(9) 0.7505(2) 0.0687(5) Uani 1 1 d . . . H3 H 0.2516 0.0222 0.6816 0.082 Uiso 1 1 calc R . . C11 C 0.95612(17) -0.16920(9) 0.8279(2) 0.0676(5) Uani 1 1 d . . . H11 H 1.0113 -0.1575 0.9261 0.081 Uiso 1 1 calc R . . C5 C 0.44180(17) 0.12380(8) 0.9379(2) 0.0689(5) Uani 1 1 d . . . H5 H 0.4383 0.1601 0.9973 0.083 Uiso 1 1 calc R . . C24 C 0.77953(17) 0.17903(9) 0.36697(19) 0.0703(5) Uani 1 1 d . . . H24 H 0.8641 0.1694 0.3714 0.084 Uiso 1 1 calc R . . C15 C 0.78511(16) -0.14056(9) 0.5908(2) 0.0684(5) Uani 1 1 d . . . H15 H 0.7225 -0.1094 0.5276 0.082 Uiso 1 1 calc R . . C21 C 0.52743(18) 0.20680(9) 0.3469(2) 0.0713(5) Uani 1 1 d . . . H21 H 0.4413 0.2156 0.3387 0.086 Uiso 1 1 calc R . . C13 C 0.8885(2) -0.25102(10) 0.6317(3) 0.0894(7) Uani 1 1 d . . . H13 H 0.8959 -0.2946 0.5972 0.107 Uiso 1 1 calc R . . C22 C 0.5778(2) 0.24524(10) 0.2662(2) 0.0809(6) Uani 1 1 d . . . H22 H 0.5270 0.2807 0.2051 0.097 Uiso 1 1 calc R . . C12 C 0.9671(2) -0.23342(11) 0.7748(3) 0.0886(6) Uani 1 1 d . . . H12 H 1.0291 -0.2649 0.8378 0.106 Uiso 1 1 calc R . . C14 C 0.7977(2) -0.20473(11) 0.5371(3) 0.0842(6) Uani 1 1 d . . . H14 H 0.7453 -0.2163 0.4381 0.101 Uiso 1 1 calc R . . C23 C 0.7039(2) 0.23097(11) 0.2761(2) 0.0856(6) Uani 1 1 d . . . H23 H 0.7382 0.2567 0.2209 0.103 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 N2 0.0391(6) 0.0530(7) 0.0530(8) 0.0020(6) 0.0175(6) -0.0005(6) N1 0.0367(6) 0.0500(7) 0.0595(8) 0.0018(6) 0.0202(6) -0.0014(6) O1 0.0471(6) 0.0959(9) 0.0717(8) -0.0286(7) 0.0142(6) -0.0082(6) C1 0.0477(8) 0.0461(8) 0.0434(8) 0.0001(7) 0.0216(7) -0.0039(7) C7 0.0478(9) 0.0582(10) 0.0458(9) -0.0019(8) 0.0202(7) -0.0047(8) C18 0.0446(8) 0.0461(8) 0.0490(9) -0.0058(7) 0.0195(7) -0.0080(7) C8 0.0481(8) 0.0541(9) 0.0572(10) -0.0006(8) 0.0281(7) -0.0042(7) C9 0.0426(8) 0.0533(9) 0.0481(9) 0.0027(8) 0.0178(7) -0.0014(7) C20 0.0589(10) 0.0542(10) 0.0588(10) -0.0034(8) 0.0242(8) -0.0022(8) C19 0.0528(9) 0.0467(8) 0.0471(9) -0.0093(7) 0.0167(7) -0.0096(8) C6 0.0603(10) 0.0631(10) 0.0637(11) -0.0148(9) 0.0266(8) -0.0085(9) C10 0.0439(8) 0.0527(9) 0.0585(10) 0.0051(8) 0.0293(8) -0.0006(7) C4 0.0571(10) 0.0657(11) 0.0723(12) 0.0025(10) 0.0329(9) 0.0100(9) C2 0.0487(9) 0.0658(11) 0.0667(11) -0.0197(9) 0.0228(8) -0.0015(8) C16 0.0378(8) 0.0723(11) 0.0910(13) 0.0164(10) 0.0294(9) 0.0022(8) C17 0.0486(10) 0.0669(11) 0.0876(13) 0.0113(10) 0.0347(9) -0.0079(8) C3 0.0462(9) 0.0812(12) 0.0739(12) -0.0192(10) 0.0210(9) -0.0016(9) C11 0.0731(11) 0.0656(11) 0.0714(12) 0.0166(10) 0.0377(10) 0.0126(9) C5 0.0777(12) 0.0588(11) 0.0818(13) -0.0144(10) 0.0450(11) 0.0003(10) C24 0.0644(10) 0.0819(12) 0.0633(11) 0.0140(10) 0.0259(9) -0.0050(10) C15 0.0617(10) 0.0741(12) 0.0684(12) -0.0059(10) 0.0266(9) 0.0031(9) C21 0.0687(11) 0.0666(11) 0.0708(12) 0.0020(10) 0.0220(10) 0.0105(10) C13 0.1155(17) 0.0548(12) 0.139(2) -0.0077(14) 0.0932(16) -0.0065(13) C22 0.0880(15) 0.0691(12) 0.0686(13) 0.0122(10) 0.0169(11) 0.0061(11) C12 0.1106(17) 0.0645(13) 0.1120(18) 0.0259(13) 0.0680(15) 0.0244(12) C14 0.0872(13) 0.0862(14) 0.0929(16) -0.0298(13) 0.0515(12) -0.0187(12) C23 0.0869(14) 0.0900(14) 0.0758(14) 0.0276(12) 0.0306(11) -0.0045(12) _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 N2 C18 1.3360(18) . ? N2 N1 1.3485(15) . ? N1 C16 1.3355(18) . ? N1 C9 1.4695(18) . ? O1 C7 1.2175(16) . ? C1 C2 1.3768(18) . ? C1 C6 1.381(2) . ? C1 C7 1.4881(19) . ? C7 C8 1.512(2) . ? C18 C17 1.390(2) . ? C18 C19 1.470(2) . ? C8 C9 1.521(2) . ? C9 C10 1.511(2) . ? C20 C21 1.376(2) . ? C20 C19 1.390(2) . ? C19 C24 1.390(2) . ? C6 C5 1.378(2) . ? C10 C15 1.377(2) . ? C10 C11 1.378(2) . ? C4 C3 1.358(2) . ? C4 C5 1.363(2) . ? C2 C3 1.377(2) . ? C16 C17 1.359(2) . ? C11 C12 1.379(3) . ? C24 C23 1.373(2) . ? C15 C14 1.386(2) . ? C21 C22 1.372(3) . ? C13 C12 1.354(3) . ? C13 C14 1.373(3) . ? C22 C23 1.375(2) . ? 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 C18 N2 N1 105.08(11) . . ? C16 N1 N2 111.55(12) . . ? C16 N1 C9 126.43(13) . . ? N2 N1 C9 122.01(11) . . ? C2 C1 C6 117.91(13) . . ? C2 C1 C7 122.97(14) . . ? C6 C1 C7 119.11(13) . . ? O1 C7 C1 120.79(14) . . ? O1 C7 C8 119.84(13) . . ? C1 C7 C8 119.30(12) . . ? N2 C18 C17 110.46(13) . . ? N2 C18 C19 120.54(12) . . ? C17 C18 C19 128.99(14) . . ? C7 C8 C9 113.67(12) . . ? N1 C9 C10 110.84(12) . . ? N1 C9 C8 109.66(11) . . ? C10 C9 C8 112.41(12) . . ? C21 C20 C19 120.70(16) . . ? C24 C19 C20 117.98(15) . . ? C24 C19 C18 120.56(14) . . ? C20 C19 C18 121.45(14) . . ? C5 C6 C1 120.74(15) . . ? C15 C10 C11 118.48(15) . . ? C15 C10 C9 121.35(14) . . ? C11 C10 C9 120.16(15) . . ? C3 C4 C5 119.85(15) . . ? C1 C2 C3 121.03(15) . . ? N1 C16 C17 107.48(13) . . ? C16 C17 C18 105.42(14) . . ? C4 C3 C2 120.22(15) . . ? C10 C11 C12 120.49(18) . . ? C4 C5 C6 120.24(16) . . ? C23 C24 C19 120.93(17) . . ? C10 C15 C14 120.93(17) . . ? C22 C21 C20 120.49(18) . . ? C12 C13 C14 120.27(19) . . ? C21 C22 C23 119.53(18) . . ? C13 C12 C11 120.51(19) . . ? C13 C14 C15 119.30(19) . . ? C24 C23 C22 120.35(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.118 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.023