data_s92 _database_code_CSD 163765 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Anderson, Rosaleen J.' 'Bendell, David' 'Coles, Simon J.' 'Garnett, Ian' 'Groundwater, P, W,' 'Hursthouse, Michael B.' 'McKillop, Alexander' 'Morton, Andrew J.' 'Nyerges, Miklos' 'Sharif, Toqir' 'Zhang, Weimin' _publ_contact_author_name 'Dr P W Groundwater' _publ_contact_author_address ; Dr P W Groundwater School of Health Sciences University of Sunderland Sunderland SR1 3SD UK ; _publ_contact_author_email 'PAUL.GROUNDWATER@SUNDERLAND.AC.UK' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H30 N2' _chemical_formula_weight 538.66 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 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 10.257(2) _cell_length_b 28.375(5) _cell_length_c 10.590(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.21(3) _cell_angle_gamma 90.00 _cell_volume 2853.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4898 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _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 8026 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.1324 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3913 _reflns_number_gt 1885 _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^)+(0.1000P)^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 0.0028(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3913 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1598 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1863 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _refine_ls_shift/su_max 0.088 _refine_ls_shift/su_mean 0.016 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 0.8458(3) 0.20388(10) 0.0813(3) 0.0341(9) Uani 1 1 d . . . N2 N 1.0737(3) 0.20781(10) 0.2150(3) 0.0363(9) Uani 1 1 d . . . C1 C 0.7009(3) 0.21671(12) -0.0015(4) 0.0371(11) Uani 1 1 d . . . H1A H 0.6591 0.1918 -0.0704 0.044 Uiso 1 1 calc R . . H1B H 0.7011 0.2463 -0.0508 0.044 Uiso 1 1 calc R . . C2 C 0.6097(4) 0.22337(12) 0.0805(5) 0.0336(11) Uani 1 1 d . . . C3 C 0.6514(4) 0.21075(13) 0.2168(5) 0.0418(12) Uani 1 1 d . . . H3 H 0.7442 0.1993 0.2643 0.050 Uiso 1 1 calc R . . C4 C 0.5600(4) 0.21453(13) 0.2845(4) 0.0411(11) Uani 1 1 d . . . H4 H 0.5896 0.2044 0.3766 0.049 Uiso 1 1 calc R . . C5 C 0.4278(4) 0.23263(13) 0.2206(5) 0.0466(12) Uani 1 1 d . . . H5 H 0.3661 0.2358 0.2681 0.056 Uiso 1 1 calc R . . C6 C 0.3855(4) 0.24615(15) 0.0859(6) 0.0593(14) Uani 1 1 d . . . H6 H 0.2938 0.2587 0.0402 0.071 Uiso 1 1 calc R . . C7 C 0.4758(4) 0.24158(14) 0.0163(5) 0.0504(13) Uani 1 1 d . . . H7 H 0.4451 0.2511 -0.0765 0.060 Uiso 1 1 calc R . . C8 C 0.9592(4) 0.23288(12) 0.1467(4) 0.0341(11) Uani 1 1 d . . . C9 C 0.9592(4) 0.28479(12) 0.1391(4) 0.0332(10) Uani 1 1 d . . . C10 C 0.8432(4) 0.31391(13) 0.1179(4) 0.0404(11) Uani 1 1 d . . . H10 H 0.7551 0.3002 0.1067 0.049 Uiso 1 1 calc R . . C11 C 0.8541(4) 0.36228(13) 0.1128(4) 0.0435(11) Uani 1 1 d . . . H11 H 0.7733 0.3814 0.0964 0.052 Uiso 1 1 calc R . . C12 C 0.9816(4) 0.38316(13) 0.1312(4) 0.0453(12) Uani 1 1 d . . . H12 H 0.9892 0.4165 0.1286 0.054 Uiso 1 1 calc R . . C13 C 1.0984(4) 0.35487(12) 0.1535(4) 0.0404(11) Uani 1 1 d . . . H13 H 1.1866 0.3689 0.1668 0.049 Uiso 1 1 calc R . . C14 C 1.0875(4) 0.30656(12) 0.1568(4) 0.0374(11) Uani 1 1 d . . . H14 H 1.1684 0.2877 0.1712 0.045 Uiso 1 1 calc R . . C15 C 0.8950(4) 0.15783(12) 0.1092(4) 0.0327(11) Uani 1 1 d . . . C16 C 1.0339(4) 0.16105(12) 0.1921(4) 0.0340(11) Uani 1 1 d . . . C17 C 0.8083(3) 0.11632(12) 0.0409(4) 0.0349(11) Uani 1 1 d . . . C18 C 0.6883(4) 0.10420(13) 0.0642(4) 0.0401(11) Uani 1 1 d . . . H18 H 0.6608 0.1232 0.1238 0.048 Uiso 1 1 calc R . . C19 C 0.6075(4) 0.06535(13) 0.0034(4) 0.0449(12) Uani 1 1 d . . . H19 H 0.5246 0.0581 0.0194 0.054 Uiso 1 1 calc R . . C20 C 0.6490(4) 0.03721(14) -0.0811(5) 0.0475(12) Uani 1 1 d . . . H20 H 0.5953 0.0102 -0.1227 0.057 Uiso 1 1 calc R . . C21 C 0.7685(4) 0.04843(12) -0.1048(4) 0.0432(12) Uani 1 1 d . . . H21 H 0.7967 0.0285 -0.1620 0.052 Uiso 1 1 calc R . . C22 C 0.8490(3) 0.08807(12) -0.0474(4) 0.0346(11) Uani 1 1 d . . . C23 C 0.9744(4) 0.09908(13) -0.0814(4) 0.0360(11) Uani 1 1 d . . . C24 C 1.0699(4) 0.06343(13) -0.0751(4) 0.0439(11) Uani 1 1 d . . . H24 H 1.0530 0.0324 -0.0516 0.053 Uiso 1 1 calc R . . C25 C 1.1883(4) 0.07255(14) -0.1026(5) 0.0488(12) Uani 1 1 d . . . H25 H 1.2522 0.0477 -0.0978 0.059 Uiso 1 1 calc R . . C26 C 1.2149(4) 0.11724(15) -0.1370(4) 0.0510(13) Uani 1 1 d . . . H26 H 1.2987 0.1237 -0.1522 0.061 Uiso 1 1 calc R . . C27 C 1.1183(4) 0.15257(14) -0.1492(4) 0.0503(12) Uani 1 1 d . . . H27 H 1.1333 0.1832 -0.1774 0.060 Uiso 1 1 calc R . . C28 C 0.9999(4) 0.14365(13) -0.1205(4) 0.0409(11) Uani 1 1 d . . . H28 H 0.9350 0.1684 -0.1277 0.049 Uiso 1 1 calc R . . C29 C 1.1376(3) 0.12288(12) 0.2475(4) 0.0349(11) Uani 1 1 d . . . C30 C 1.2631(4) 0.12565(13) 0.2248(4) 0.0408(11) Uani 1 1 d . . . H30 H 1.2799 0.1524 0.1792 0.049 Uiso 1 1 calc R . . C31 C 1.3633(4) 0.09051(14) 0.2667(4) 0.0467(12) Uani 1 1 d . . . H31 H 1.4493 0.0937 0.2530 0.056 Uiso 1 1 calc R . . C32 C 1.3376(4) 0.05045(14) 0.3290(4) 0.0446(12) Uani 1 1 d . . . H32 H 1.4047 0.0256 0.3557 0.054 Uiso 1 1 calc R . . C33 C 1.2142(4) 0.04680(13) 0.3520(4) 0.0429(12) Uani 1 1 d . . . H33 H 1.1973 0.0193 0.3947 0.051 Uiso 1 1 calc R . . C34 C 1.1131(4) 0.08281(13) 0.3138(4) 0.0379(11) Uani 1 1 d . . . C35 C 0.9887(4) 0.07870(13) 0.3542(4) 0.0386(11) Uani 1 1 d . . . C36 C 0.9089(4) 0.03754(14) 0.3280(4) 0.0497(12) Uani 1 1 d . . . H36 H 0.9316 0.0122 0.2812 0.060 Uiso 1 1 calc R . . C37 C 0.7971(4) 0.03320(16) 0.3698(5) 0.0570(14) Uani 1 1 d . . . H37 H 0.7436 0.0049 0.3518 0.068 Uiso 1 1 calc R . . C38 C 0.7625(4) 0.06993(17) 0.4377(5) 0.0612(14) Uani 1 1 d . . . H38 H 0.6852 0.0670 0.4658 0.073 Uiso 1 1 calc R . . C39 C 0.8407(4) 0.11055(16) 0.4640(5) 0.0560(13) Uani 1 1 d . . . H39 H 0.8179 0.1357 0.5114 0.067 Uiso 1 1 calc R . . C40 C 0.9522(4) 0.11522(14) 0.4223(4) 0.0478(12) Uani 1 1 d . . . H40 H 1.0048 0.1437 0.4403 0.057 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 N1 0.0330(19) 0.0321(18) 0.038(3) 0.0027(16) 0.0144(18) 0.0004(13) N2 0.0395(19) 0.0330(18) 0.037(3) -0.0027(17) 0.0155(18) 0.0002(13) C1 0.031(2) 0.037(2) 0.037(3) 0.008(2) 0.006(2) 0.0039(15) C2 0.031(2) 0.031(2) 0.039(3) 0.000(2) 0.013(2) 0.0014(15) C3 0.037(3) 0.042(2) 0.043(4) 0.002(2) 0.012(3) 0.0014(16) C4 0.041(3) 0.048(2) 0.037(3) -0.004(2) 0.017(3) -0.0034(18) C5 0.041(3) 0.049(3) 0.054(4) -0.006(3) 0.022(3) 0.0024(18) C6 0.038(3) 0.080(3) 0.061(4) 0.004(3) 0.019(3) 0.012(2) C7 0.043(3) 0.061(3) 0.044(4) 0.007(2) 0.013(3) 0.0111(19) C8 0.034(2) 0.035(2) 0.035(3) -0.003(2) 0.016(2) 0.0000(16) C9 0.038(2) 0.035(2) 0.026(3) -0.0022(19) 0.011(2) 0.0007(16) C10 0.038(2) 0.041(2) 0.039(3) -0.001(2) 0.011(2) -0.0009(17) C11 0.048(3) 0.037(2) 0.042(3) -0.001(2) 0.012(2) 0.0062(17) C12 0.058(3) 0.028(2) 0.045(4) 0.001(2) 0.015(3) 0.0008(18) C13 0.044(2) 0.038(2) 0.039(3) 0.004(2) 0.015(2) -0.0084(17) C14 0.038(2) 0.036(2) 0.040(3) 0.001(2) 0.017(2) 0.0018(16) C15 0.036(2) 0.030(2) 0.035(3) 0.0026(19) 0.017(2) -0.0001(15) C16 0.032(2) 0.030(2) 0.039(3) 0.0005(19) 0.012(2) -0.0002(15) C17 0.030(2) 0.030(2) 0.041(3) 0.001(2) 0.010(2) 0.0011(15) C18 0.038(2) 0.038(2) 0.045(3) 0.003(2) 0.016(2) 0.0026(17) C19 0.037(2) 0.037(2) 0.060(4) 0.007(2) 0.017(3) -0.0052(17) C20 0.041(3) 0.033(2) 0.063(4) 0.000(2) 0.013(3) -0.0071(17) C21 0.045(2) 0.030(2) 0.052(4) -0.001(2) 0.015(2) -0.0002(17) C22 0.033(2) 0.031(2) 0.038(3) 0.006(2) 0.011(2) 0.0031(15) C23 0.038(2) 0.037(2) 0.030(3) -0.004(2) 0.009(2) -0.0017(16) C24 0.048(3) 0.036(2) 0.050(3) -0.003(2) 0.021(2) -0.0003(17) C25 0.045(3) 0.043(3) 0.059(4) -0.004(2) 0.021(3) 0.0046(18) C26 0.045(3) 0.059(3) 0.050(4) 0.001(3) 0.019(3) -0.001(2) C27 0.051(3) 0.046(3) 0.057(4) 0.006(2) 0.024(3) -0.0074(19) C28 0.041(2) 0.037(2) 0.045(3) -0.002(2) 0.016(2) 0.0008(16) C29 0.035(2) 0.031(2) 0.034(3) -0.009(2) 0.007(2) 0.0001(15) C30 0.034(2) 0.042(2) 0.046(3) -0.002(2) 0.014(2) -0.0019(16) C31 0.034(2) 0.052(3) 0.049(4) -0.007(2) 0.010(2) 0.0041(18) C32 0.039(2) 0.040(2) 0.045(3) -0.006(2) 0.005(2) 0.0095(17) C33 0.050(3) 0.034(2) 0.041(3) 0.001(2) 0.013(2) 0.0026(17) C34 0.038(2) 0.036(2) 0.036(3) -0.003(2) 0.011(2) 0.0011(16) C35 0.039(2) 0.040(2) 0.031(3) 0.003(2) 0.006(2) 0.0029(17) C36 0.055(3) 0.042(2) 0.053(4) 0.003(2) 0.022(3) -0.0037(19) C37 0.053(3) 0.057(3) 0.057(4) 0.019(3) 0.016(3) -0.012(2) C38 0.056(3) 0.074(4) 0.057(4) 0.018(3) 0.026(3) 0.005(2) C39 0.055(3) 0.063(3) 0.056(4) 0.011(3) 0.028(3) 0.010(2) C40 0.045(3) 0.044(2) 0.054(4) 0.003(2) 0.018(3) 0.0016(18) _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 C8 1.379(4) . ? N1 C15 1.392(4) . ? N1 C1 1.458(4) . ? N2 C8 1.329(4) . ? N2 C16 1.382(4) . ? C1 C2 1.510(5) . ? C2 C7 1.382(5) . ? C2 C3 1.388(5) . ? C3 C4 1.383(5) . ? C4 C5 1.367(5) . ? C5 C6 1.380(6) . ? C6 C7 1.391(5) . ? C8 C9 1.475(5) . ? C9 C10 1.395(4) . ? C9 C14 1.401(4) . ? C10 C11 1.380(5) . ? C11 C12 1.380(5) . ? C12 C13 1.386(5) . ? C13 C14 1.377(5) . ? C15 C16 1.365(5) . ? C15 C17 1.488(5) . ? C16 C29 1.475(4) . ? C17 C18 1.388(4) . ? C17 C22 1.410(5) . ? C18 C19 1.384(5) . ? C19 C20 1.380(5) . ? C20 C21 1.379(5) . ? C21 C22 1.392(5) . ? C22 C23 1.494(5) . ? C23 C28 1.386(5) . ? C23 C24 1.392(5) . ? C24 C25 1.376(5) . ? C25 C26 1.375(5) . ? C26 C27 1.381(5) . ? C27 C28 1.382(5) . ? C29 C30 1.399(5) . ? C29 C34 1.408(5) . ? C30 C31 1.379(5) . ? C31 C32 1.389(5) . ? C32 C33 1.381(5) . ? C33 C34 1.402(5) . ? C34 C35 1.496(5) . ? C35 C40 1.392(5) . ? C35 C36 1.392(5) . ? C36 C37 1.382(5) . ? C37 C38 1.387(6) . ? C38 C39 1.371(6) . ? C39 C40 1.380(5) . ? 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 C8 N1 C15 106.5(3) . . ? C8 N1 C1 128.9(3) . . ? C15 N1 C1 124.6(3) . . ? C8 N2 C16 106.1(3) . . ? N1 C1 C2 113.4(3) . . ? C7 C2 C3 117.9(4) . . ? C7 C2 C1 118.7(4) . . ? C3 C2 C1 123.4(3) . . ? C4 C3 C2 121.1(4) . . ? C5 C4 C3 120.9(4) . . ? C4 C5 C6 118.8(4) . . ? C5 C6 C7 120.7(4) . . ? C2 C7 C6 120.7(4) . . ? N2 C8 N1 111.0(3) . . ? N2 C8 C9 123.1(3) . . ? N1 C8 C9 125.9(3) . . ? C10 C9 C14 117.5(3) . . ? C10 C9 C8 125.6(3) . . ? C14 C9 C8 116.9(3) . . ? C11 C10 C9 121.2(3) . . ? C10 C11 C12 120.5(3) . . ? C11 C12 C13 119.1(3) . . ? C14 C13 C12 120.6(3) . . ? C13 C14 C9 121.1(3) . . ? C16 C15 N1 106.3(3) . . ? C16 C15 C17 130.7(3) . . ? N1 C15 C17 122.5(3) . . ? C15 C16 N2 110.1(3) . . ? C15 C16 C29 128.8(3) . . ? N2 C16 C29 120.9(3) . . ? C18 C17 C22 118.8(3) . . ? C18 C17 C15 121.1(3) . . ? C22 C17 C15 120.0(3) . . ? C17 C18 C19 122.0(4) . . ? C20 C19 C18 119.0(4) . . ? C19 C20 C21 119.8(4) . . ? C20 C21 C22 122.0(4) . . ? C21 C22 C17 118.3(3) . . ? C21 C22 C23 119.1(4) . . ? C17 C22 C23 122.6(3) . . ? C28 C23 C24 118.0(3) . . ? C28 C23 C22 122.6(3) . . ? C24 C23 C22 119.4(3) . . ? C25 C24 C23 121.0(4) . . ? C24 C25 C26 120.6(4) . . ? C25 C26 C27 119.1(4) . . ? C26 C27 C28 120.4(4) . . ? C27 C28 C23 120.9(3) . . ? C30 C29 C34 118.7(3) . . ? C30 C29 C16 117.5(3) . . ? C34 C29 C16 123.6(3) . . ? C31 C30 C29 121.8(4) . . ? C30 C31 C32 119.5(3) . . ? C33 C32 C31 119.8(3) . . ? C32 C33 C34 121.4(4) . . ? C33 C34 C29 118.8(3) . . ? C33 C34 C35 118.6(3) . . ? C29 C34 C35 122.5(3) . . ? C40 C35 C36 118.3(4) . . ? C40 C35 C34 121.0(3) . . ? C36 C35 C34 120.6(4) . . ? C37 C36 C35 120.5(4) . . ? C36 C37 C38 120.3(4) . . ? C39 C38 C37 119.5(4) . . ? C38 C39 C40 120.5(4) . . ? C39 C40 C35 120.8(4) . . ? _diffrn_measured_fraction_theta_max 0.597 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.597 _refine_diff_density_max 0.185 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.048