data_tora13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H28 N8' _chemical_formula_sum 'C44 H28 N8' _chemical_formula_weight 668.74 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)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 8.3433(9) _cell_length_b 12.0224(13) _cell_length_c 15.8306(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.373(2) _cell_angle_gamma 90.00 _cell_volume 1571.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 4438 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.04 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9416 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details 'sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11563 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3674 _reflns_number_gt 2654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0963P)^2^+0.1109P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3674 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.96804(17) 0.12813(11) 0.07621(10) 0.0364(4) Uani 1 1 d . . . N2 N 0.53747(19) -0.23933(12) -0.19094(10) 0.0404(4) Uani 1 1 d . . . N3 N 0.86708(19) -0.12870(13) 0.17084(10) 0.0462(4) Uani 1 1 d . . . N4 N 0.6104(2) -0.33418(12) 0.02101(11) 0.0450(4) Uani 1 1 d . . . C1 C 0.63642(19) -0.09083(12) 0.02334(10) 0.0305(4) Uani 1 1 d . . . H1A H 0.7102 -0.1516 0.0465 0.037 Uiso 1 1 calc R . . C2 C 0.73394(19) 0.01627(12) 0.02774(10) 0.0291(4) Uani 1 1 d . . . C3 C 0.8811(2) 0.03405(13) 0.08121(11) 0.0309(4) Uani 1 1 d . . . C4 C 0.9079(2) 0.20659(13) 0.02131(12) 0.0378(4) Uani 1 1 d . . . H4A H 0.9707 0.2706 0.0164 0.045 Uiso 1 1 calc R . . C5 C 0.7586(2) 0.19932(13) -0.02888(11) 0.0346(4) Uani 1 1 d . . . H5A H 0.7177 0.2588 -0.0642 0.042 Uiso 1 1 calc R . . C6 C 0.67101(19) 0.10266(12) -0.02593(10) 0.0306(4) Uani 1 1 d . . . C7 C 0.5078(2) 0.08431(12) -0.07950(11) 0.0310(4) Uani 1 1 d . . . H7A H 0.4907 0.1421 -0.1244 0.037 Uiso 1 1 calc R . . C8 C 0.51315(19) -0.02816(12) -0.12139(11) 0.0310(4) Uani 1 1 d . . . C9 C 0.4622(2) -0.04706(14) -0.20693(11) 0.0371(4) Uani 1 1 d . . . H9A H 0.4177 0.0106 -0.2431 0.044 Uiso 1 1 calc R . . C10 C 0.4784(2) -0.15359(15) -0.23810(12) 0.0414(4) Uani 1 1 d . . . H10A H 0.4453 -0.1658 -0.2967 0.050 Uiso 1 1 calc R . . C11 C 0.5840(2) -0.22127(13) -0.10653(11) 0.0336(4) Uani 1 1 d . . . C12 C 0.57631(19) -0.11655(12) -0.06932(11) 0.0309(4) Uani 1 1 d . . . C13 C 0.9572(2) -0.04569(13) 0.14731(11) 0.0329(4) Uani 1 1 d . . . C14 C 1.1176(2) -0.03239(15) 0.18319(12) 0.0420(4) Uani 1 1 d . . . H14A H 1.1770 0.0296 0.1689 0.050 Uiso 1 1 calc R . . C15 C 1.1894(2) -0.11071(17) 0.23991(13) 0.0476(5) Uani 1 1 d . . . H15A H 1.2989 -0.1037 0.2637 0.057 Uiso 1 1 calc R . . C16 C 1.1000(3) -0.19870(17) 0.26129(13) 0.0492(5) Uani 1 1 d . . . H16A H 1.1471 -0.2545 0.2985 0.059 Uiso 1 1 calc R . . C17 C 0.9389(3) -0.20331(17) 0.22679(13) 0.0510(5) Uani 1 1 d . . . H17A H 0.8759 -0.2620 0.2434 0.061 Uiso 1 1 calc R . . C18 C 0.6462(2) -0.32219(13) -0.05771(12) 0.0353(4) Uani 1 1 d . . . C19 C 0.7374(2) -0.39976(14) -0.09521(13) 0.0426(4) Uani 1 1 d . . . H19A H 0.7603 -0.3887 -0.1510 0.051 Uiso 1 1 calc R . . C20 C 0.7937(3) -0.49269(15) -0.04998(15) 0.0500(5) Uani 1 1 d . . . H20A H 0.8553 -0.5463 -0.0742 0.060 Uiso 1 1 calc R . . C21 C 0.7578(3) -0.50569(16) 0.03203(15) 0.0570(6) Uani 1 1 d . . . H21A H 0.7948 -0.5681 0.0649 0.068 Uiso 1 1 calc R . . C22 C 0.6673(3) -0.42560(16) 0.06403(15) 0.0553(6) Uani 1 1 d . . . H22A H 0.6433 -0.4351 0.1198 0.066 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 0.0344(8) 0.0313(7) 0.0417(9) -0.0045(6) -0.0001(6) -0.0027(6) N2 0.0415(9) 0.0374(7) 0.0404(9) -0.0085(6) -0.0005(7) -0.0024(6) N3 0.0417(9) 0.0493(9) 0.0452(10) 0.0102(7) -0.0015(7) -0.0038(7) N4 0.0553(10) 0.0307(7) 0.0498(10) 0.0019(7) 0.0102(8) 0.0026(7) C1 0.0314(8) 0.0248(7) 0.0336(9) -0.0002(6) -0.0010(7) -0.0009(6) C2 0.0311(9) 0.0248(7) 0.0310(9) -0.0019(6) 0.0029(7) -0.0008(6) C3 0.0312(8) 0.0285(7) 0.0324(9) -0.0041(6) 0.0029(7) -0.0001(6) C4 0.0390(10) 0.0265(7) 0.0470(11) -0.0037(7) 0.0035(8) -0.0056(7) C5 0.0385(10) 0.0268(7) 0.0375(10) 0.0016(7) 0.0025(7) -0.0010(6) C6 0.0313(8) 0.0283(7) 0.0314(9) -0.0014(6) 0.0018(7) -0.0008(6) C7 0.0344(9) 0.0249(7) 0.0318(9) 0.0019(6) -0.0008(7) -0.0017(6) C8 0.0294(8) 0.0283(7) 0.0343(9) -0.0011(6) 0.0015(7) -0.0024(6) C9 0.0359(9) 0.0377(8) 0.0356(10) 0.0019(7) -0.0013(7) -0.0014(7) C10 0.0422(10) 0.0444(9) 0.0351(10) -0.0070(8) -0.0031(8) -0.0038(8) C11 0.0299(8) 0.0305(7) 0.0394(10) -0.0041(7) 0.0020(7) -0.0028(6) C12 0.0294(8) 0.0279(7) 0.0342(9) -0.0011(6) 0.0007(7) -0.0035(6) C13 0.0329(9) 0.0333(8) 0.0319(9) -0.0028(7) 0.0031(7) 0.0011(7) C14 0.0382(10) 0.0432(9) 0.0426(11) 0.0002(8) -0.0006(8) -0.0017(8) C15 0.0394(10) 0.0561(11) 0.0444(12) 0.0059(9) -0.0032(8) 0.0032(9) C16 0.0510(12) 0.0536(11) 0.0412(11) 0.0114(9) 0.0008(9) 0.0066(9) C17 0.0502(12) 0.0510(11) 0.0501(12) 0.0166(9) 0.0019(9) -0.0041(9) C18 0.0340(9) 0.0265(7) 0.0436(10) -0.0043(7) -0.0006(7) -0.0047(6) C19 0.0453(10) 0.0342(8) 0.0475(11) -0.0087(8) 0.0038(8) -0.0034(8) C20 0.0529(12) 0.0306(8) 0.0649(14) -0.0085(9) 0.0038(10) 0.0059(8) C21 0.0732(15) 0.0320(9) 0.0644(15) 0.0055(9) 0.0054(12) 0.0089(9) C22 0.0778(15) 0.0366(9) 0.0534(13) 0.0077(9) 0.0157(11) 0.0063(9) _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 C4 1.330(2) . ? N1 C3 1.352(2) . ? N2 C10 1.325(2) . ? N2 C11 1.354(2) . ? N3 C13 1.335(2) . ? N3 C17 1.339(2) . ? N4 C18 1.331(2) . ? N4 C22 1.343(2) . ? C1 C12 1.511(2) . ? C1 C2 1.519(2) . ? C1 C7 1.599(2) 3_655 ? C1 H1A 0.9900 . ? C2 C6 1.395(2) . ? C2 C3 1.402(2) . ? C3 C13 1.491(2) . ? C4 C5 1.380(2) . ? C4 H4A 0.9400 . ? C5 C6 1.377(2) . ? C5 H5A 0.9400 . ? C6 C7 1.512(2) . ? C7 C8 1.510(2) . ? C7 C1 1.599(2) 3_655 ? C7 H7A 0.9900 . ? C8 C9 1.378(2) . ? C8 C12 1.400(2) . ? C9 C10 1.386(2) . ? C9 H9A 0.9400 . ? C10 H10A 0.9400 . ? C11 C12 1.396(2) . ? C11 C18 1.491(2) . ? C13 C14 1.385(2) . ? C14 C15 1.377(3) . ? C14 H14A 0.9400 . ? C15 C16 1.365(3) . ? C15 H15A 0.9400 . ? C16 C17 1.377(3) . ? C16 H16A 0.9400 . ? C17 H17A 0.9400 . ? C18 C19 1.390(2) . ? C19 C20 1.372(3) . ? C19 H19A 0.9400 . ? C20 C21 1.383(3) . ? C20 H20A 0.9400 . ? C21 C22 1.366(3) . ? C21 H21A 0.9400 . ? C22 H22A 0.9400 . ? 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 C4 N1 C3 118.48(14) . . ? C10 N2 C11 117.46(14) . . ? C13 N3 C17 118.00(16) . . ? C18 N4 C22 116.89(16) . . ? C12 C1 C2 108.52(13) . . ? C12 C1 C7 112.30(13) . 3_655 ? C2 C1 C7 111.98(12) . 3_655 ? C12 C1 H1A 108.0 . . ? C2 C1 H1A 108.0 . . ? C7 C1 H1A 108.0 3_655 . ? C6 C2 C3 118.22(14) . . ? C6 C2 C1 116.84(13) . . ? C3 C2 C1 124.94(14) . . ? N1 C3 C2 121.48(14) . . ? N1 C3 C13 113.66(14) . . ? C2 C3 C13 124.86(14) . . ? N1 C4 C5 123.65(15) . . ? N1 C4 H4A 118.2 . . ? C5 C4 H4A 118.2 . . ? C6 C5 C4 118.25(15) . . ? C6 C5 H5A 120.9 . . ? C4 C5 H5A 120.9 . . ? C5 C6 C2 119.62(15) . . ? C5 C6 C7 122.91(14) . . ? C2 C6 C7 117.47(13) . . ? C8 C7 C6 107.18(13) . . ? C8 C7 C1 111.17(12) . 3_655 ? C6 C7 C1 111.74(13) . 3_655 ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C1 C7 H7A 108.9 3_655 . ? C9 C8 C12 119.30(15) . . ? C9 C8 C7 123.70(15) . . ? C12 C8 C7 116.99(14) . . ? C8 C9 C10 118.03(16) . . ? C8 C9 H9A 121.0 . . ? C10 C9 H9A 121.0 . . ? N2 C10 C9 124.46(17) . . ? N2 C10 H10A 117.8 . . ? C9 C10 H10A 117.8 . . ? N2 C11 C12 122.50(15) . . ? N2 C11 C18 114.17(14) . . ? C12 C11 C18 123.32(16) . . ? C11 C12 C8 118.21(15) . . ? C11 C12 C1 124.41(14) . . ? C8 C12 C1 117.35(13) . . ? N3 C13 C14 121.46(16) . . ? N3 C13 C3 118.47(15) . . ? C14 C13 C3 120.08(16) . . ? C15 C14 C13 119.43(18) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C16 C15 C14 119.35(18) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C15 C16 C17 118.04(18) . . ? C15 C16 H16A 121.0 . . ? C17 C16 H16A 121.0 . . ? N3 C17 C16 123.54(18) . . ? N3 C17 H17A 118.2 . . ? C16 C17 H17A 118.2 . . ? N4 C18 C19 122.59(16) . . ? N4 C18 C11 117.69(15) . . ? C19 C18 C11 119.72(17) . . ? C20 C19 C18 119.37(19) . . ? C20 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C19 C20 C21 118.49(19) . . ? C19 C20 H20A 120.8 . . ? C21 C20 H20A 120.8 . . ? C22 C21 C20 118.40(19) . . ? C22 C21 H21A 120.8 . . ? C20 C21 H21A 120.8 . . ? N4 C22 C21 124.3(2) . . ? N4 C22 H22A 117.9 . . ? C21 C22 H22A 117.9 . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.324 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.057