data_k1039a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N2' _chemical_formula_sum 'C26 H20 N2' _chemical_formula_weight 360.44 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 Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.6734(5) _cell_length_b 8.9202(7) _cell_length_c 11.2248(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1869.72(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 11923 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.4 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.075 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 11923 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.37 _reflns_number_total 2217 _reflns_number_gt 1456 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A. L. (2009). Acta Cryst. D65, 148--155. ; _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^)+(0.0619P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _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 3(5) _refine_ls_number_reflns 2217 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _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 0.63877(13) 0.2450(3) 0.4084(3) 0.0298(7) Uani 1 1 d . . . N2 N 0.76398(13) 0.2263(3) 0.3679(3) 0.0288(7) Uani 1 1 d . . . C1 C 0.70898(15) 0.2989(3) 0.4480(3) 0.0262(7) Uani 1 1 d . . . C2 C 0.72662(16) 0.2455(4) 0.5762(3) 0.0310(8) Uani 1 1 d . . . H2A H 0.7356 0.3318 0.6297 0.037 Uiso 1 1 calc R . . H2B H 0.6871 0.1845 0.6094 0.037 Uiso 1 1 calc R . . C3 C 0.79292(16) 0.1532(4) 0.5604(3) 0.0289(8) Uani 1 1 d . . . C4 C 0.83369(17) 0.0798(4) 0.6476(3) 0.0335(8) Uani 1 1 d . . . H4A H 0.8227 0.0925 0.7297 0.040 Uiso 1 1 calc R . . C5 C 0.88898(17) -0.0097(4) 0.6140(4) 0.0359(9) Uani 1 1 d . . . H5A H 0.9163 -0.0598 0.6732 0.043 Uiso 1 1 calc R . . C6 C 0.90678(17) -0.0297(4) 0.4921(3) 0.0316(8) Uani 1 1 d . . . C7 C 0.96196(16) -0.1294(4) 0.4556(4) 0.0383(9) Uani 1 1 d . . . H7A H 0.9885 -0.1827 0.5141 0.046 Uiso 1 1 calc R . . C8 C 0.97745(17) -0.1498(4) 0.3381(4) 0.0416(10) Uani 1 1 d . . . H8A H 1.0138 -0.2186 0.3155 0.050 Uiso 1 1 calc R . . C9 C 0.94001(17) -0.0697(4) 0.2501(3) 0.0375(9) Uani 1 1 d . . . H9A H 0.9516 -0.0838 0.1685 0.045 Uiso 1 1 calc R . . C10 C 0.88688(15) 0.0285(4) 0.2814(3) 0.0328(9) Uani 1 1 d . . . H10A H 0.8627 0.0835 0.2211 0.039 Uiso 1 1 calc R . . C11 C 0.86756(16) 0.0491(4) 0.4022(3) 0.0296(8) Uani 1 1 d . . . C12 C 0.80945(16) 0.1399(3) 0.4420(3) 0.0271(8) Uani 1 1 d . . . C13 C 0.72353(15) 0.1510(4) 0.2723(3) 0.0316(8) Uani 1 1 d . . . H13A H 0.7376 0.0445 0.2650 0.038 Uiso 1 1 calc R . . H13B H 0.7309 0.2016 0.1948 0.038 Uiso 1 1 calc R . . C14 C 0.64676(16) 0.1658(4) 0.3137(3) 0.0293(8) Uani 1 1 d . . . C15 C 0.58610(16) 0.0976(4) 0.2486(3) 0.0328(9) Uani 1 1 d . . . C16 C 0.59817(19) -0.0094(4) 0.1619(4) 0.0414(10) Uani 1 1 d . . . H16A H 0.6458 -0.0404 0.1451 0.050 Uiso 1 1 calc R . . C17 C 0.5415(2) -0.0723(4) 0.0988(4) 0.0478(11) Uani 1 1 d . . . H17A H 0.5503 -0.1464 0.0398 0.057 Uiso 1 1 calc R . . C18 C 0.47221(19) -0.0263(5) 0.1223(4) 0.0454(11) Uani 1 1 d . . . H18A H 0.4334 -0.0682 0.0790 0.054 Uiso 1 1 calc R . . C19 C 0.45951(18) 0.0800(4) 0.2085(4) 0.0432(10) Uani 1 1 d . . . H19A H 0.4118 0.1104 0.2251 0.052 Uiso 1 1 calc R . . C20 C 0.51581(16) 0.1431(4) 0.2712(4) 0.0375(9) Uani 1 1 d . . . H20A H 0.5066 0.2176 0.3297 0.045 Uiso 1 1 calc R . . C21 C 0.71260(16) 0.4688(3) 0.4410(3) 0.0266(7) Uani 1 1 d . . . C22 C 0.65295(18) 0.5555(4) 0.4671(3) 0.0319(8) Uani 1 1 d . . . H22A H 0.6085 0.5080 0.4837 0.038 Uiso 1 1 calc R . . C23 C 0.65744(19) 0.7113(4) 0.4690(3) 0.0361(9) Uani 1 1 d . . . H23A H 0.6164 0.7696 0.4878 0.043 Uiso 1 1 calc R . . C24 C 0.72173(18) 0.7808(4) 0.4437(4) 0.0393(9) Uani 1 1 d . . . H24A H 0.7250 0.8871 0.4451 0.047 Uiso 1 1 calc R . . C25 C 0.78110(18) 0.6961(4) 0.4164(4) 0.0397(9) Uani 1 1 d . . . H25A H 0.8253 0.7440 0.3986 0.048 Uiso 1 1 calc R . . C26 C 0.77654(17) 0.5410(4) 0.4148(3) 0.0346(9) Uani 1 1 d . . . H26A H 0.8177 0.4834 0.3955 0.042 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 0.0306(14) 0.0277(15) 0.0311(17) 0.0010(15) 0.0003(12) -0.0041(11) N2 0.0278(14) 0.0304(15) 0.0283(16) -0.0011(13) -0.0008(12) 0.0009(12) C1 0.0242(16) 0.0288(17) 0.0255(19) 0.0008(17) -0.0002(13) -0.0023(13) C2 0.0372(19) 0.031(2) 0.024(2) 0.0020(16) 0.0004(15) -0.0008(15) C3 0.0315(17) 0.0261(19) 0.029(2) -0.0016(16) -0.0020(15) -0.0059(13) C4 0.0352(19) 0.036(2) 0.029(2) 0.0013(17) -0.0027(16) -0.0015(16) C5 0.0337(17) 0.041(2) 0.033(2) 0.0060(18) -0.0057(15) -0.0002(15) C6 0.0322(17) 0.0297(18) 0.033(2) 0.0009(17) -0.0015(16) -0.0034(14) C7 0.0304(18) 0.044(2) 0.041(3) 0.0005(19) -0.0053(17) 0.0034(15) C8 0.0331(18) 0.046(2) 0.045(3) -0.004(2) -0.0003(17) 0.0038(16) C9 0.0320(18) 0.052(2) 0.029(2) -0.0019(19) 0.0042(16) 0.0021(16) C10 0.0295(18) 0.037(2) 0.032(2) 0.0006(18) -0.0039(14) -0.0039(14) C11 0.0283(16) 0.0263(18) 0.034(2) -0.0008(17) -0.0002(15) -0.0034(13) C12 0.0303(16) 0.0245(17) 0.027(2) 0.0040(16) -0.0021(15) -0.0066(13) C13 0.0321(17) 0.036(2) 0.027(2) 0.0001(17) -0.0012(15) -0.0006(14) C14 0.0334(17) 0.0273(17) 0.027(2) 0.0032(17) -0.0017(15) -0.0013(13) C15 0.0318(18) 0.033(2) 0.033(2) 0.0002(18) -0.0020(15) -0.0047(14) C16 0.037(2) 0.042(2) 0.045(3) -0.004(2) -0.0049(17) -0.0004(16) C17 0.051(3) 0.044(2) 0.048(3) -0.011(2) -0.0092(19) -0.0048(18) C18 0.042(2) 0.047(2) 0.046(3) 0.005(2) -0.0126(19) -0.0152(18) C19 0.030(2) 0.050(2) 0.050(3) 0.007(2) -0.0034(17) -0.0067(16) C20 0.0331(19) 0.041(2) 0.038(2) 0.0038(19) -0.0007(16) -0.0027(15) C21 0.0337(16) 0.0253(16) 0.0207(18) 0.0000(16) -0.0003(13) -0.0034(13) C22 0.0346(18) 0.035(2) 0.026(2) -0.0021(17) 0.0014(15) -0.0015(15) C23 0.043(2) 0.034(2) 0.031(2) -0.0007(17) 0.0031(16) 0.0038(16) C24 0.050(2) 0.0277(18) 0.040(2) 0.0006(19) -0.0051(18) -0.0075(16) C25 0.0417(19) 0.038(2) 0.039(2) 0.0001(19) -0.0032(17) -0.0133(16) C26 0.0328(17) 0.039(2) 0.032(2) -0.0021(18) -0.0012(15) -0.0031(14) _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 C14 1.285(4) . ? N1 C1 1.466(4) . ? N2 C12 1.416(4) . ? N2 C13 1.474(4) . ? N2 C1 1.511(4) . ? C1 C21 1.519(4) . ? C1 C2 1.551(5) . ? C2 C3 1.497(4) . ? C3 C12 1.370(5) . ? C3 C4 1.402(5) . ? C4 C5 1.359(5) . ? C5 C6 1.419(5) . ? C6 C7 1.422(5) . ? C6 C11 1.432(5) . ? C7 C8 1.362(6) . ? C8 C9 1.405(6) . ? C9 C10 1.369(5) . ? C10 C11 1.415(5) . ? C11 C12 1.426(4) . ? C13 C14 1.513(4) . ? C14 C15 1.479(5) . ? C15 C16 1.382(5) . ? C15 C20 1.397(5) . ? C16 C17 1.392(5) . ? C17 C18 1.382(5) . ? C18 C19 1.375(6) . ? C19 C20 1.385(5) . ? C21 C22 1.387(4) . ? C21 C26 1.388(4) . ? C22 C23 1.392(5) . ? C23 C24 1.381(5) . ? C24 C25 1.376(5) . ? C25 C26 1.386(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 C14 N1 C1 109.1(3) . . ? C12 N2 C13 119.2(3) . . ? C12 N2 C1 106.9(3) . . ? C13 N2 C1 106.3(2) . . ? N1 C1 N2 106.7(3) . . ? N1 C1 C21 110.6(2) . . ? N2 C1 C21 111.5(2) . . ? N1 C1 C2 111.8(3) . . ? N2 C1 C2 106.0(2) . . ? C21 C1 C2 110.2(3) . . ? C3 C2 C1 103.6(3) . . ? C12 C3 C4 121.0(3) . . ? C12 C3 C2 110.4(3) . . ? C4 C3 C2 128.5(3) . . ? C5 C4 C3 119.5(3) . . ? C4 C5 C6 121.3(3) . . ? C5 C6 C7 121.8(3) . . ? C5 C6 C11 119.9(3) . . ? C7 C6 C11 118.3(3) . . ? C8 C7 C6 121.1(3) . . ? C7 C8 C9 120.5(3) . . ? C10 C9 C8 120.4(4) . . ? C9 C10 C11 120.9(3) . . ? C10 C11 C12 124.6(3) . . ? C10 C11 C6 118.8(3) . . ? C12 C11 C6 116.6(3) . . ? C3 C12 N2 112.8(3) . . ? C3 C12 C11 121.7(3) . . ? N2 C12 C11 125.5(3) . . ? N2 C13 C14 102.9(3) . . ? N1 C14 C15 123.1(3) . . ? N1 C14 C13 114.3(3) . . ? C15 C14 C13 122.6(3) . . ? C16 C15 C20 118.8(3) . . ? C16 C15 C14 120.5(3) . . ? C20 C15 C14 120.7(3) . . ? C15 C16 C17 120.9(3) . . ? C18 C17 C16 119.6(4) . . ? C19 C18 C17 120.0(3) . . ? C18 C19 C20 120.5(3) . . ? C19 C20 C15 120.2(4) . . ? C22 C21 C26 118.5(3) . . ? C22 C21 C1 120.6(3) . . ? C26 C21 C1 120.8(3) . . ? C21 C22 C23 120.7(3) . . ? C24 C23 C22 119.8(3) . . ? C25 C24 C23 120.0(3) . . ? C24 C25 C26 120.1(3) . . ? C25 C26 C21 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.37 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.204 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.051