Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_3gl _database_code_CSD 164080 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'He, Hai-Ying' 'Katritzky, A.' 'Steel, P. J.' 'Xu, Yong-Jiang' _publ_contact_author_name 'Prof A Katritzky' _publ_contact_author_address ; Prof A Katritzky Department of Chemistry University of Florida Gainesville FL 32611 USA ; _publ_contact_author_email 'KATRITZKY@CHEM.UFL.EDU' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N2 O2' _chemical_formula_weight 368.42 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 P2(1)/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 12.132(4) _cell_length_b 8.462(3) _cell_length_c 18.708(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.806(5) _cell_angle_gamma 90.00 _cell_volume 1873.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(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 21057 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3297 _reflns_number_gt 2393 _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^)+(0.0544P)^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_number_reflns 3297 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.002 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.75426(8) 0.56628(11) 0.20986(5) 0.0326(3) Uani 1 1 d . . . O2 O 0.35359(8) 0.58446(11) 0.06792(5) 0.0333(3) Uani 1 1 d . . . N1 N 0.69624(9) 0.72140(12) 0.10699(6) 0.0246(3) Uani 1 1 d . . . N2 N 0.50854(8) 0.74785(12) 0.10805(6) 0.0233(3) Uani 1 1 d . . . C1 C 0.68174(11) 0.64219(15) 0.16818(7) 0.0253(3) Uani 1 1 d . . . C2 C 0.56092(11) 0.67033(16) 0.17739(7) 0.0254(3) Uani 1 1 d . . . H2A H 0.5225 0.5678 0.1826 0.030 Uiso 1 1 calc R . . C3 C 0.42551(11) 0.67466(15) 0.05507(8) 0.0250(3) Uani 1 1 d . . . C4 C 0.44460(11) 0.72636(15) -0.01701(7) 0.0240(3) Uani 1 1 d . . . C5 C 0.37728(12) 0.70319(16) -0.08667(8) 0.0310(4) Uani 1 1 d . . . H5A H 0.3067 0.6501 -0.0935 0.037 Uiso 1 1 calc R . . C6 C 0.41671(13) 0.76026(17) -0.14582(8) 0.0351(4) Uani 1 1 d . . . H6A H 0.3726 0.7463 -0.1941 0.042 Uiso 1 1 calc R . . C7 C 0.52045(12) 0.83794(17) -0.13526(8) 0.0346(4) Uani 1 1 d . . . H7A H 0.5461 0.8752 -0.1767 0.042 Uiso 1 1 calc R . . C8 C 0.58712(12) 0.86203(16) -0.06549(8) 0.0306(3) Uani 1 1 d . . . H8A H 0.6572 0.9164 -0.0586 0.037 Uiso 1 1 calc R . . C9 C 0.54812(11) 0.80413(15) -0.00612(7) 0.0250(3) Uani 1 1 d . . . C10 C 0.59617(10) 0.81813(15) 0.07510(7) 0.0244(3) Uani 1 1 d . . . H10A H 0.6090 0.9314 0.0899 0.029 Uiso 1 1 calc R . . C11 C 0.56786(11) 0.77278(16) 0.24517(7) 0.0294(3) Uani 1 1 d . . . H11A H 0.6204 0.7212 0.2866 0.035 Uiso 1 1 calc R . . H11B H 0.6019 0.8753 0.2364 0.035 Uiso 1 1 calc R . . C12 C 0.45832(11) 0.80634(15) 0.26870(7) 0.0263(3) Uani 1 1 d . . . C13 C 0.35753(12) 0.72850(17) 0.24059(8) 0.0336(4) Uani 1 1 d . . . H13A H 0.3535 0.6554 0.2015 0.040 Uiso 1 1 calc R . . C14 C 0.26177(12) 0.75565(18) 0.26869(9) 0.0379(4) Uani 1 1 d . . . H14A H 0.1937 0.7001 0.2490 0.045 Uiso 1 1 calc R . . C15 C 0.26538(12) 0.86217(17) 0.32456(8) 0.0347(4) Uani 1 1 d . . . H15A H 0.2007 0.8792 0.3444 0.042 Uiso 1 1 calc R . . C16 C 0.36405(13) 0.94408(17) 0.35157(8) 0.0359(4) Uani 1 1 d . . . H16A H 0.3666 1.0198 0.3894 0.043 Uiso 1 1 calc R . . C17 C 0.45992(12) 0.91730(16) 0.32409(8) 0.0325(4) Uani 1 1 d . . . H17A H 0.5271 0.9751 0.3432 0.039 Uiso 1 1 calc R . . C18 C 0.80641(10) 0.76094(15) 0.09530(8) 0.0252(3) Uani 1 1 d . . . C19 C 0.84598(11) 0.69314(16) 0.03825(8) 0.0304(3) Uani 1 1 d . . . H19A H 0.8006 0.6199 0.0061 0.037 Uiso 1 1 calc R . . C20 C 0.95321(12) 0.73376(17) 0.02869(9) 0.0346(4) Uani 1 1 d . . . H20A H 0.9801 0.6875 -0.0105 0.041 Uiso 1 1 calc R . . C21 C 1.02156(11) 0.83990(17) 0.07486(9) 0.0342(4) Uani 1 1 d . . . C22 C 0.97980(12) 0.90604(18) 0.13156(9) 0.0393(4) Uani 1 1 d . . . H22A H 1.0253 0.9787 0.1640 0.047 Uiso 1 1 calc R . . C23 C 0.87288(12) 0.86800(17) 0.14180(8) 0.0346(4) Uani 1 1 d . . . H23A H 0.8455 0.9153 0.1806 0.042 Uiso 1 1 calc R . . C24 C 1.13833(12) 0.8821(2) 0.06383(10) 0.0487(5) Uani 1 1 d . . . H24A H 1.1447 0.8501 0.0146 0.073 Uiso 0.50 1 calc PR A 1 H24B H 1.1958 0.8270 0.1004 0.073 Uiso 0.50 1 calc PR A 1 H24C H 1.1498 0.9965 0.0694 0.073 Uiso 0.50 1 calc PR A 1 H24D H 1.1310 0.9485 0.0201 0.073 Uiso 0.50 1 calc PR A 2 H24E H 1.1793 0.7852 0.0575 0.073 Uiso 0.50 1 calc PR A 2 H24F H 1.1800 0.9399 0.1068 0.073 Uiso 0.50 1 calc PR A 2 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 0.0273(5) 0.0352(6) 0.0326(6) 0.0027(5) 0.0007(5) 0.0069(5) O2 0.0273(5) 0.0365(6) 0.0368(6) 0.0011(5) 0.0084(5) -0.0077(5) N1 0.0177(6) 0.0259(6) 0.0297(7) 0.0008(5) 0.0041(5) 0.0022(5) N2 0.0193(6) 0.0263(6) 0.0247(6) -0.0002(5) 0.0056(5) 0.0003(5) C1 0.0243(8) 0.0252(7) 0.0253(8) -0.0053(6) 0.0027(6) 0.0001(6) C2 0.0227(7) 0.0263(7) 0.0266(8) 0.0007(6) 0.0042(6) 0.0006(6) C3 0.0200(7) 0.0244(7) 0.0300(8) -0.0013(6) 0.0043(6) 0.0032(6) C4 0.0232(7) 0.0223(7) 0.0269(8) -0.0002(6) 0.0062(6) 0.0042(6) C5 0.0298(8) 0.0290(8) 0.0322(9) -0.0031(7) 0.0027(7) 0.0032(6) C6 0.0425(9) 0.0341(8) 0.0268(9) -0.0016(7) 0.0034(7) 0.0124(7) C7 0.0422(9) 0.0347(8) 0.0307(9) 0.0079(7) 0.0159(7) 0.0152(7) C8 0.0262(8) 0.0297(8) 0.0380(9) 0.0061(7) 0.0113(7) 0.0060(6) C9 0.0242(8) 0.0227(7) 0.0290(8) 0.0017(6) 0.0078(6) 0.0064(6) C10 0.0187(7) 0.0225(7) 0.0320(8) -0.0002(6) 0.0057(6) 0.0015(5) C11 0.0268(8) 0.0325(8) 0.0286(8) -0.0017(6) 0.0053(6) -0.0007(6) C12 0.0283(8) 0.0279(7) 0.0234(8) 0.0033(6) 0.0070(6) 0.0017(6) C13 0.0317(9) 0.0370(8) 0.0336(9) -0.0092(7) 0.0103(7) -0.0020(7) C14 0.0309(9) 0.0425(9) 0.0430(10) -0.0067(8) 0.0142(7) -0.0048(7) C15 0.0373(9) 0.0315(8) 0.0403(10) 0.0019(7) 0.0192(7) 0.0044(7) C16 0.0470(10) 0.0297(8) 0.0338(9) -0.0048(7) 0.0149(8) 0.0012(7) C17 0.0341(8) 0.0304(8) 0.0330(9) -0.0014(7) 0.0072(7) -0.0038(7) C18 0.0184(7) 0.0259(7) 0.0308(8) 0.0018(6) 0.0043(6) 0.0020(6) C19 0.0256(8) 0.0313(8) 0.0345(9) -0.0024(7) 0.0069(7) 0.0005(6) C20 0.0273(8) 0.0399(9) 0.0387(9) 0.0015(7) 0.0122(7) 0.0050(7) C21 0.0213(8) 0.0358(8) 0.0444(10) 0.0125(7) 0.0047(7) 0.0018(6) C22 0.0282(8) 0.0400(9) 0.0468(10) -0.0056(8) 0.0019(7) -0.0086(7) C23 0.0288(8) 0.0369(8) 0.0379(9) -0.0080(7) 0.0067(7) -0.0020(7) C24 0.0259(8) 0.0525(10) 0.0683(12) 0.0156(9) 0.0113(8) -0.0025(7) _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 C1 1.2208(15) . ? O2 C3 1.2227(15) . ? N1 C1 1.3712(17) . ? N1 C18 1.4409(16) . ? N1 C10 1.4761(16) . ? N2 C3 1.3922(17) . ? N2 C2 1.4669(17) . ? N2 C10 1.4678(16) . ? C1 C2 1.5321(19) . ? C2 C11 1.5228(19) . ? C3 C4 1.4838(19) . ? C4 C5 1.3900(19) . ? C4 C9 1.3923(18) . ? C5 C6 1.386(2) . ? C6 C7 1.395(2) . ? C7 C8 1.390(2) . ? C8 C9 1.3895(19) . ? C9 C10 1.5067(19) . ? C11 C12 1.5166(18) . ? C12 C13 1.3860(19) . ? C12 C17 1.3953(19) . ? C13 C14 1.3963(19) . ? C14 C15 1.374(2) . ? C15 C16 1.379(2) . ? C16 C17 1.390(2) . ? C18 C23 1.3846(19) . ? C18 C19 1.388(2) . ? C19 C20 1.3949(19) . ? C20 C21 1.387(2) . ? C21 C22 1.390(2) . ? C21 C24 1.519(2) . ? C22 C23 1.390(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 C1 N1 C18 122.36(11) . . ? C1 N1 C10 111.24(10) . . ? C18 N1 C10 121.16(10) . . ? C3 N2 C2 122.28(11) . . ? C3 N2 C10 111.00(11) . . ? C2 N2 C10 109.91(10) . . ? O1 C1 N1 125.65(12) . . ? O1 C1 C2 125.59(12) . . ? N1 C1 C2 108.72(11) . . ? N2 C2 C11 114.52(11) . . ? N2 C2 C1 101.99(10) . . ? C11 C2 C1 107.72(10) . . ? O2 C3 N2 124.96(13) . . ? O2 C3 C4 128.66(13) . . ? N2 C3 C4 106.37(11) . . ? C5 C4 C9 121.83(13) . . ? C5 C4 C3 129.26(13) . . ? C9 C4 C3 108.90(12) . . ? C6 C5 C4 117.67(14) . . ? C5 C6 C7 120.76(14) . . ? C8 C7 C6 121.41(14) . . ? C9 C8 C7 117.94(14) . . ? C8 C9 C4 120.38(13) . . ? C8 C9 C10 130.86(13) . . ? C4 C9 C10 108.63(11) . . ? N2 C10 N1 102.30(10) . . ? N2 C10 C9 103.73(10) . . ? N1 C10 C9 117.63(11) . . ? C12 C11 C2 117.26(11) . . ? C13 C12 C17 117.87(13) . . ? C13 C12 C11 123.85(12) . . ? C17 C12 C11 118.22(12) . . ? C12 C13 C14 121.11(14) . . ? C15 C14 C13 120.38(14) . . ? C14 C15 C16 119.17(14) . . ? C15 C16 C17 120.81(14) . . ? C16 C17 C12 120.61(13) . . ? C23 C18 C19 120.08(13) . . ? C23 C18 N1 119.16(12) . . ? C19 C18 N1 120.76(12) . . ? C18 C19 C20 119.22(13) . . ? C21 C20 C19 121.71(14) . . ? C20 C21 C22 117.86(13) . . ? C20 C21 C24 120.97(14) . . ? C22 C21 C24 121.16(14) . . ? C23 C22 C21 121.38(14) . . ? C18 C23 C22 119.75(14) . . ? 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 C18 N1 C1 O1 -17.6(2) . . . . ? C10 N1 C1 O1 -172.24(12) . . . . ? C18 N1 C1 C2 160.08(11) . . . . ? C10 N1 C1 C2 5.45(14) . . . . ? C3 N2 C2 C11 -132.76(12) . . . . ? C10 N2 C2 C11 94.44(13) . . . . ? C3 N2 C2 C1 111.20(12) . . . . ? C10 N2 C2 C1 -21.60(13) . . . . ? O1 C1 C2 N2 -172.58(12) . . . . ? N1 C1 C2 N2 9.73(13) . . . . ? O1 C1 C2 C11 66.54(16) . . . . ? N1 C1 C2 C11 -111.15(12) . . . . ? C2 N2 C3 O2 34.52(19) . . . . ? C10 N2 C3 O2 166.88(12) . . . . ? C2 N2 C3 C4 -144.55(11) . . . . ? C10 N2 C3 C4 -12.19(13) . . . . ? O2 C3 C4 C5 9.9(2) . . . . ? N2 C3 C4 C5 -171.13(12) . . . . ? O2 C3 C4 C9 -168.52(13) . . . . ? N2 C3 C4 C9 10.51(14) . . . . ? C9 C4 C5 C6 0.09(19) . . . . ? C3 C4 C5 C6 -178.09(12) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C9 0.9(2) . . . . ? C7 C8 C9 C4 -0.78(19) . . . . ? C7 C8 C9 C10 -176.25(13) . . . . ? C5 C4 C9 C8 0.29(19) . . . . ? C3 C4 C9 C8 178.80(11) . . . . ? C5 C4 C9 C10 176.67(12) . . . . ? C3 C4 C9 C10 -4.82(14) . . . . ? C3 N2 C10 N1 -113.60(11) . . . . ? C2 N2 C10 N1 24.76(13) . . . . ? C3 N2 C10 C9 9.21(13) . . . . ? C2 N2 C10 C9 147.56(10) . . . . ? C1 N1 C10 N2 -18.27(13) . . . . ? C18 N1 C10 N2 -173.25(10) . . . . ? C1 N1 C10 C9 -131.12(12) . . . . ? C18 N1 C10 C9 73.90(15) . . . . ? C8 C9 C10 N2 173.55(13) . . . . ? C4 C9 C10 N2 -2.32(13) . . . . ? C8 C9 C10 N1 -74.41(18) . . . . ? C4 C9 C10 N1 109.72(13) . . . . ? N2 C2 C11 C12 71.79(15) . . . . ? C1 C2 C11 C12 -175.54(11) . . . . ? C2 C11 C12 C13 11.7(2) . . . . ? C2 C11 C12 C17 -171.16(12) . . . . ? C17 C12 C13 C14 -2.4(2) . . . . ? C11 C12 C13 C14 174.77(13) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C13 C14 C15 C16 1.2(2) . . . . ? C14 C15 C16 C17 -1.5(2) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C13 C12 C17 C16 2.2(2) . . . . ? C11 C12 C17 C16 -175.20(13) . . . . ? C1 N1 C18 C23 -65.92(17) . . . . ? C10 N1 C18 C23 86.26(16) . . . . ? C1 N1 C18 C19 114.11(15) . . . . ? C10 N1 C18 C19 -93.70(15) . . . . ? C23 C18 C19 C20 0.2(2) . . . . ? N1 C18 C19 C20 -179.79(12) . . . . ? C18 C19 C20 C21 0.2(2) . . . . ? C19 C20 C21 C22 -0.2(2) . . . . ? C19 C20 C21 C24 179.70(13) . . . . ? C20 C21 C22 C23 -0.2(2) . . . . ? C24 C21 C22 C23 179.87(14) . . . . ? C19 C18 C23 C22 -0.7(2) . . . . ? N1 C18 C23 C22 179.38(12) . . . . ? C21 C22 C23 C18 0.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.150 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.042