# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Jingsong You' _publ_contact_author_name 'Jingsong You' _publ_contact_author_address ; Professor of Chemistry Director of Professor Committee of Chemistry College of Chemistry Sichuan University 29 Wangjiang Road, Chengdu 610064, People's Republic of China ; _publ_contact_author_email jsyou@scu.edu.cn data_yjs8m _database_code_depnum_ccdc_archive 'CCDC 806283' #TrackingRef '(R)-1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H18 N4 O2' _chemical_formula_sum 'C26 H18 N4 O2' _chemical_formula_weight 418.44 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 21 21 2' _symmetry_int_tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 27.513(3) _cell_length_b 12.2721(11) _cell_length_c 12.3143(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4157.8(7) _cell_formula_units_Z 6 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4437 _cell_measurement_theta_min 2.341 _cell_measurement_theta_max 23.097 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.003 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9525 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 23774 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4556 _reflns_number_gt 2584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1500P)^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 constro _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(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(10) _refine_ls_number_reflns 4556 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1438 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2554 _refine_ls_wR_factor_gt 0.2112 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 O1 O 0.84958(14) 1.1114(3) 0.7292(4) 0.0645(12) Uani 1 1 d . . . H1A H 0.8475 1.0480 0.7500 0.097 Uiso 1 1 calc R . . O2 O 0.73820(17) 0.9159(3) 0.5939(3) 0.0638(12) Uani 1 1 d . . . H2A H 0.7403 0.9808 0.5786 0.096 Uiso 1 1 calc R . . O3 O 0.98939(14) 0.6617(3) 0.7512(4) 0.0733(13) Uani 1 1 d . . . H3B H 1.0170 0.6369 0.7539 0.110 Uiso 1 1 calc R . . N1 N 0.84795(17) 1.3219(4) 0.6596(4) 0.0568(13) Uani 1 1 d . . . N2 N 0.9224(2) 1.3836(5) 0.6843(5) 0.0757(17) Uani 1 1 d . . . N3 N 0.73166(18) 0.7102(3) 0.6620(4) 0.0561(13) Uani 1 1 d . . . N4 N 0.7330(2) 0.5822(4) 0.5353(5) 0.0734(15) Uani 1 1 d . . . N5 N 0.89741(17) 0.7355(4) 0.7593(5) 0.0642(14) Uani 1 1 d . . . N6 N 0.87222(18) 0.9020(4) 0.7241(6) 0.0718(16) Uani 1 1 d . . . C1 C 0.8885(2) 1.3192(5) 0.7226(6) 0.0661(18) Uani 1 1 d . . . H1B H 0.8918 1.2771 0.7849 0.079 Uiso 1 1 calc R . . C2 C 0.9030(3) 1.4291(6) 0.5923(7) 0.084(2) Uani 1 1 d . . . H2B H 0.9189 1.4784 0.5474 0.101 Uiso 1 1 calc R . . C3 C 0.8573(3) 1.3922(6) 0.5766(6) 0.074(2) Uani 1 1 d . . . H3A H 0.8365 1.4109 0.5202 0.089 Uiso 1 1 calc R . . C4 C 0.80309(19) 1.2647(4) 0.6774(5) 0.0527(14) Uani 1 1 d . . . C5 C 0.7600(2) 1.3131(4) 0.6551(5) 0.0564(15) Uani 1 1 d . . . H5A H 0.7597 1.3849 0.6311 0.068 Uiso 1 1 calc R . . C6 C 0.7155(2) 1.2572(4) 0.6675(5) 0.0494(13) Uani 1 1 d . . . C7 C 0.6709(2) 1.3053(5) 0.6414(6) 0.0645(17) Uani 1 1 d . . . H7A H 0.6706 1.3756 0.6133 0.077 Uiso 1 1 calc R . . C8 C 0.6285(3) 1.2528(7) 0.6558(7) 0.085(2) Uani 1 1 d . . . H8A H 0.5994 1.2866 0.6374 0.102 Uiso 1 1 calc R . . C9 C 0.6284(3) 1.1454(6) 0.6994(7) 0.084(2) Uani 1 1 d . . . H9A H 0.5991 1.1090 0.7101 0.101 Uiso 1 1 calc R . . C10 C 0.6711(2) 1.0961(6) 0.7253(6) 0.0682(17) Uani 1 1 d . . . H10A H 0.6707 1.0262 0.7545 0.082 Uiso 1 1 calc R . . C11 C 0.7164(2) 1.1501(5) 0.7084(5) 0.0519(14) Uani 1 1 d . . . C12 C 0.7618(2) 1.0982(4) 0.7309(4) 0.0488(13) Uani 1 1 d . . . C13 C 0.8047(2) 1.1525(4) 0.7149(5) 0.0519(14) Uani 1 1 d . . . C14 C 0.7628(2) 0.9818(4) 0.7704(5) 0.0478(13) Uani 1 1 d . . . C15 C 0.7761(2) 0.9572(5) 0.8780(5) 0.0516(14) Uani 1 1 d . . . C16 C 0.7918(2) 1.0367(5) 0.9527(5) 0.0658(17) Uani 1 1 d . . . H16A H 0.7920 1.1096 0.9320 0.079 Uiso 1 1 calc R . . C17 C 0.8067(3) 1.0096(7) 1.0538(6) 0.082(2) Uani 1 1 d . . . H17A H 0.8184 1.0634 1.1000 0.099 Uiso 1 1 calc R . . C18 C 0.8047(3) 0.9036(8) 1.0892(6) 0.096(3) Uani 1 1 d . . . H18A H 0.8140 0.8871 1.1599 0.115 Uiso 1 1 calc R . . C19 C 0.7888(3) 0.8202(7) 1.0205(5) 0.077(2) Uani 1 1 d . . . H19A H 0.7875 0.7485 1.0450 0.093 Uiso 1 1 calc R . . C20 C 0.7750(2) 0.8464(5) 0.9139(5) 0.0578(15) Uani 1 1 d . . . C21 C 0.7595(2) 0.7655(5) 0.8395(5) 0.0548(14) Uani 1 1 d . . . H21A H 0.7578 0.6933 0.8621 0.066 Uiso 1 1 calc R . . C22 C 0.7474(2) 0.7908(4) 0.7373(5) 0.0516(14) Uani 1 1 d . . . C23 C 0.7497(2) 0.9015(4) 0.6993(5) 0.0499(13) Uani 1 1 d . . . C24 C 0.6847(3) 0.6879(5) 0.6319(6) 0.0740(19) Uani 1 1 d . . . H24A H 0.6569 0.7217 0.6583 0.089 Uiso 1 1 calc R . . C25 C 0.6864(3) 0.6086(5) 0.5576(6) 0.076(2) Uani 1 1 d . . . H25A H 0.6594 0.5761 0.5259 0.091 Uiso 1 1 calc R . . C26 C 0.7601(3) 0.6453(5) 0.6001(6) 0.0689(18) Uani 1 1 d . . . H26A H 0.7939 0.6446 0.6022 0.083 Uiso 1 1 calc R . . C27 C 0.8826(2) 0.8314(5) 0.8004(6) 0.0636(17) Uani 1 1 d . . . H27A H 0.8800 0.8459 0.8744 0.076 Uiso 1 1 calc R . . C28 C 0.8822(3) 0.8501(7) 0.6285(8) 0.094(3) Uani 1 1 d . . . H28A H 0.8790 0.8811 0.5600 0.112 Uiso 1 1 calc R . . C29 C 0.8974(3) 0.7474(7) 0.6478(7) 0.090(3) Uani 1 1 d . . . H29A H 0.9061 0.6953 0.5966 0.108 Uiso 1 1 calc R . . C30 C 0.9107(2) 0.6408(5) 0.8203(5) 0.0576(16) Uani 1 1 d . . . C31 C 0.8771(2) 0.5888(5) 0.8808(6) 0.0716(19) Uani 1 1 d . . . H31A H 0.8451 0.6133 0.8808 0.086 Uiso 1 1 calc R . . C32 C 0.8900(2) 0.4974(6) 0.9442(6) 0.0731(19) Uani 1 1 d . . . C33 C 0.8541(3) 0.4377(8) 1.0031(9) 0.121(4) Uani 1 1 d . . . H33A H 0.8218 0.4604 1.0023 0.146 Uiso 1 1 calc R . . C34 C 0.8673(4) 0.3460(9) 1.0614(11) 0.144(5) Uani 1 1 d . . . H34A H 0.8441 0.3058 1.0990 0.173 Uiso 1 1 calc R . . C35 C 0.9163(4) 0.3147(9) 1.0629(10) 0.144(5) Uani 1 1 d . . . H35A H 0.9252 0.2545 1.1042 0.173 Uiso 1 1 calc R . . C36 C 0.9508(3) 0.3680(6) 1.0072(7) 0.089(2) Uani 1 1 d . . . H36A H 0.9826 0.3425 1.0086 0.106 Uiso 1 1 calc R . . C37 C 0.9395(2) 0.4623(5) 0.9464(6) 0.0644(17) Uani 1 1 d . . . C38 C 0.97408(19) 0.5181(4) 0.8814(5) 0.0524(14) Uani 1 1 d . . . C39 C 0.96048(19) 0.6052(4) 0.8182(5) 0.0524(14) Uani 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 O1 0.053(2) 0.0380(19) 0.103(3) 0.000(2) -0.019(2) 0.0075(16) O2 0.092(3) 0.0364(19) 0.063(3) 0.0033(19) -0.021(2) -0.009(2) O3 0.047(2) 0.054(2) 0.119(3) 0.027(3) 0.020(2) 0.0084(18) N1 0.055(3) 0.037(2) 0.079(3) 0.004(3) -0.017(3) -0.004(2) N2 0.062(3) 0.056(3) 0.110(5) -0.005(3) -0.023(3) -0.002(3) N3 0.062(3) 0.032(2) 0.074(3) -0.003(2) 0.006(3) -0.007(2) N4 0.103(5) 0.042(3) 0.075(4) -0.006(3) -0.008(3) 0.005(3) N5 0.053(3) 0.048(3) 0.091(4) 0.000(3) 0.000(3) 0.019(2) N6 0.055(3) 0.054(3) 0.106(5) 0.002(4) 0.002(3) 0.013(2) C1 0.057(4) 0.048(3) 0.094(5) -0.002(4) -0.027(4) -0.001(3) C2 0.072(5) 0.064(4) 0.116(6) 0.009(5) -0.014(5) -0.021(4) C3 0.080(5) 0.055(4) 0.088(5) 0.010(4) -0.026(4) -0.013(3) C4 0.045(3) 0.037(3) 0.076(4) -0.004(3) -0.013(3) -0.001(2) C5 0.064(4) 0.040(3) 0.065(4) 0.001(3) -0.020(3) 0.011(3) C6 0.050(3) 0.041(3) 0.058(3) -0.003(3) -0.015(3) 0.008(2) C7 0.049(4) 0.056(4) 0.088(5) 0.001(4) -0.014(3) 0.009(3) C8 0.065(5) 0.082(5) 0.108(6) 0.010(5) -0.023(4) 0.015(4) C9 0.055(4) 0.071(4) 0.128(6) 0.008(5) -0.009(4) 0.001(3) C10 0.058(4) 0.062(4) 0.085(5) 0.007(4) -0.002(3) 0.000(3) C11 0.051(3) 0.047(3) 0.058(3) -0.005(3) -0.009(3) 0.005(2) C12 0.055(3) 0.034(2) 0.057(3) 0.000(3) -0.007(3) 0.005(2) C13 0.049(3) 0.035(3) 0.072(4) -0.005(3) -0.017(3) 0.005(2) C14 0.047(3) 0.039(3) 0.057(3) 0.000(3) -0.006(3) 0.004(2) C15 0.050(3) 0.047(3) 0.057(3) -0.002(3) 0.000(3) 0.011(2) C16 0.076(4) 0.061(4) 0.060(4) -0.007(3) -0.010(3) 0.013(3) C17 0.099(6) 0.086(5) 0.061(4) -0.004(4) -0.012(4) -0.001(4) C18 0.120(7) 0.109(7) 0.058(4) 0.016(5) -0.013(4) -0.001(5) C19 0.088(5) 0.084(5) 0.060(4) 0.018(4) -0.007(4) 0.002(4) C20 0.053(4) 0.064(4) 0.056(4) 0.011(3) 0.006(3) 0.004(3) C21 0.057(3) 0.042(3) 0.066(4) 0.011(3) 0.004(3) 0.000(3) C22 0.054(3) 0.038(3) 0.063(4) 0.001(3) 0.003(3) -0.003(2) C23 0.057(3) 0.038(3) 0.055(3) 0.003(3) -0.001(3) 0.001(2) C24 0.061(4) 0.057(4) 0.104(6) -0.015(4) -0.005(4) -0.005(3) C25 0.078(5) 0.051(4) 0.099(5) -0.004(4) -0.012(4) -0.008(3) C26 0.075(4) 0.047(3) 0.085(5) -0.006(4) 0.005(4) 0.005(3) C27 0.061(4) 0.048(3) 0.082(4) 0.000(4) 0.005(3) 0.017(3) C28 0.099(6) 0.086(5) 0.095(6) 0.008(5) -0.009(5) 0.040(5) C29 0.122(7) 0.069(5) 0.079(5) -0.010(4) -0.011(5) 0.041(5) C30 0.041(3) 0.045(3) 0.087(4) 0.004(3) 0.008(3) 0.015(2) C31 0.044(3) 0.057(4) 0.114(5) 0.004(4) 0.011(4) 0.017(3) C32 0.056(4) 0.066(4) 0.097(5) 0.012(4) 0.022(4) 0.007(3) C33 0.085(6) 0.111(7) 0.169(9) 0.037(7) 0.071(6) 0.021(5) C34 0.120(8) 0.108(7) 0.205(12) 0.072(9) 0.069(8) 0.007(6) C35 0.119(8) 0.111(7) 0.201(11) 0.086(8) 0.076(8) 0.039(6) C36 0.076(5) 0.083(5) 0.107(6) 0.037(5) 0.020(4) 0.024(4) C37 0.058(4) 0.055(4) 0.081(4) 0.008(3) 0.015(3) 0.007(3) C38 0.039(3) 0.041(3) 0.078(4) 0.001(3) 0.004(3) 0.009(2) C39 0.036(3) 0.043(3) 0.078(4) 0.004(3) 0.006(3) 0.004(2) _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 C13 1.345(6) . ? O1 H1A 0.8200 . ? O2 C23 1.347(7) . ? O2 H2A 0.8200 . ? O3 C39 1.339(6) . ? O3 H3B 0.8200 . ? N1 C1 1.359(8) . ? N1 C3 1.362(8) . ? N1 C4 1.437(7) . ? N2 C1 1.311(9) . ? N2 C2 1.371(9) . ? N3 C26 1.352(8) . ? N3 C24 1.371(8) . ? N3 C22 1.424(7) . ? N4 C26 1.339(8) . ? N4 C25 1.351(9) . ? N5 C27 1.345(8) . ? N5 C29 1.380(10) . ? N5 C30 1.431(8) . ? N6 C27 1.310(8) . ? N6 C28 1.367(10) . ? C1 H1B 0.9300 . ? C2 C3 1.349(9) . ? C2 H2B 0.9300 . ? C3 H3A 0.9300 . ? C4 C5 1.355(8) . ? C4 C13 1.452(8) . ? C5 C6 1.411(8) . ? C5 H5A 0.9300 . ? C6 C7 1.398(8) . ? C6 C11 1.408(8) . ? C7 C8 1.344(10) . ? C7 H7A 0.9300 . ? C8 C9 1.423(11) . ? C8 H8A 0.9300 . ? C9 C10 1.358(9) . ? C9 H9A 0.9300 . ? C10 C11 1.427(8) . ? C10 H10A 0.9300 . ? C11 C12 1.431(7) . ? C12 C13 1.369(8) . ? C12 C14 1.510(7) . ? C14 C23 1.367(8) . ? C14 C15 1.407(8) . ? C15 C16 1.410(8) . ? C15 C20 1.430(8) . ? C16 C17 1.352(10) . ? C16 H16A 0.9300 . ? C17 C18 1.373(11) . ? C17 H17A 0.9300 . ? C18 C19 1.398(11) . ? C18 H18A 0.9300 . ? C19 C20 1.405(9) . ? C19 H19A 0.9300 . ? C20 C21 1.417(8) . ? C21 C22 1.338(8) . ? C21 H21A 0.9300 . ? C22 C23 1.439(7) . ? C24 C25 1.336(10) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C28 C29 1.348(11) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? C30 C31 1.347(9) . ? C30 C39 1.439(7) . ? C31 C32 1.413(10) . ? C31 H31A 0.9300 . ? C32 C37 1.427(8) . ? C32 C33 1.429(10) . ? C33 C34 1.384(13) . ? C33 H33A 0.9300 . ? C34 C35 1.401(14) . ? C34 H34A 0.9300 . ? C35 C36 1.342(11) . ? C35 H35A 0.9300 . ? C36 C37 1.414(9) . ? C36 H36A 0.9300 . ? C37 C38 1.419(8) . ? C38 C39 1.374(8) . ? C38 C38 1.494(10) 2_765 ? 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 C13 O1 H1A 109.5 . . ? C23 O2 H2A 109.5 . . ? C39 O3 H3B 109.5 . . ? C1 N1 C3 106.7(5) . . ? C1 N1 C4 127.3(5) . . ? C3 N1 C4 125.9(5) . . ? C1 N2 C2 105.3(6) . . ? C26 N3 C24 106.0(5) . . ? C26 N3 C22 126.9(5) . . ? C24 N3 C22 126.9(5) . . ? C26 N4 C25 105.6(6) . . ? C27 N5 C29 106.4(6) . . ? C27 N5 C30 126.2(6) . . ? C29 N5 C30 127.5(6) . . ? C27 N6 C28 105.4(5) . . ? N2 C1 N1 111.4(6) . . ? N2 C1 H1B 124.3 . . ? N1 C1 H1B 124.3 . . ? C3 C2 N2 110.2(7) . . ? C3 C2 H2B 124.9 . . ? N2 C2 H2B 124.9 . . ? C2 C3 N1 106.3(6) . . ? C2 C3 H3A 126.8 . . ? N1 C3 H3A 126.8 . . ? C5 C4 N1 120.4(5) . . ? C5 C4 C13 120.5(5) . . ? N1 C4 C13 119.0(5) . . ? C4 C5 C6 121.6(5) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C7 C6 C11 119.4(5) . . ? C7 C6 C5 122.1(5) . . ? C11 C6 C5 118.5(5) . . ? C8 C7 C6 121.9(6) . . ? C8 C7 H7A 119.0 . . ? C6 C7 H7A 119.0 . . ? C7 C8 C9 119.7(6) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C10 C9 C8 120.0(7) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C9 C10 C11 120.8(6) . . ? C9 C10 H10A 119.6 . . ? C11 C10 H10A 119.6 . . ? C6 C11 C10 118.1(5) . . ? C6 C11 C12 120.0(5) . . ? C10 C11 C12 121.9(5) . . ? C13 C12 C11 120.6(5) . . ? C13 C12 C14 119.4(5) . . ? C11 C12 C14 120.0(5) . . ? O1 C13 C12 126.1(5) . . ? O1 C13 C4 115.2(5) . . ? C12 C13 C4 118.7(5) . . ? C23 C14 C15 121.1(5) . . ? C23 C14 C12 118.1(5) . . ? C15 C14 C12 120.7(5) . . ? C16 C15 C14 123.1(5) . . ? C16 C15 C20 117.6(5) . . ? C14 C15 C20 119.4(5) . . ? C17 C16 C15 121.6(7) . . ? C17 C16 H16A 119.2 . . ? C15 C16 H16A 119.2 . . ? C16 C17 C18 120.9(8) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C17 C18 C19 120.9(7) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C18 C19 C20 118.9(7) . . ? C18 C19 H19A 120.6 . . ? C20 C19 H19A 120.6 . . ? C19 C20 C21 121.7(6) . . ? C19 C20 C15 120.1(6) . . ? C21 C20 C15 118.2(5) . . ? C22 C21 C20 121.4(5) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 N3 121.9(5) . . ? C21 C22 C23 121.0(5) . . ? N3 C22 C23 117.2(5) . . ? O2 C23 C14 125.7(5) . . ? O2 C23 C22 115.3(5) . . ? C14 C23 C22 118.9(5) . . ? C25 C24 N3 107.3(6) . . ? C25 C24 H24A 126.3 . . ? N3 C24 H24A 126.3 . . ? C24 C25 N4 110.3(6) . . ? C24 C25 H25A 124.9 . . ? N4 C25 H25A 124.9 . . ? N4 C26 N3 110.7(6) . . ? N4 C26 H26A 124.6 . . ? N3 C26 H26A 124.6 . . ? N6 C27 N5 112.0(6) . . ? N6 C27 H27A 124.0 . . ? N5 C27 H27A 124.0 . . ? C29 C28 N6 110.2(8) . . ? C29 C28 H28A 124.9 . . ? N6 C28 H28A 124.9 . . ? C28 C29 N5 105.9(7) . . ? C28 C29 H29A 127.0 . . ? N5 C29 H29A 127.0 . . ? C31 C30 N5 120.0(5) . . ? C31 C30 C39 121.2(5) . . ? N5 C30 C39 118.7(5) . . ? C30 C31 C32 120.6(5) . . ? C30 C31 H31A 119.7 . . ? C32 C31 H31A 119.7 . . ? C31 C32 C37 119.3(6) . . ? C31 C32 C33 120.9(7) . . ? C37 C32 C33 119.8(7) . . ? C34 C33 C32 119.8(8) . . ? C34 C33 H33A 120.1 . . ? C32 C33 H33A 120.1 . . ? C33 C34 C35 118.9(9) . . ? C33 C34 H34A 120.5 . . ? C35 C34 H34A 120.5 . . ? C36 C35 C34 122.7(9) . . ? C36 C35 H35A 118.7 . . ? C34 C35 H35A 118.7 . . ? C35 C36 C37 121.0(7) . . ? C35 C36 H36A 119.5 . . ? C37 C36 H36A 119.5 . . ? C36 C37 C38 123.1(6) . . ? C36 C37 C32 117.8(6) . . ? C38 C37 C32 118.9(6) . . ? C39 C38 C37 120.8(5) . . ? C39 C38 C38 119.4(5) . 2_765 ? C37 C38 C38 119.8(5) . 2_765 ? O3 C39 C38 126.2(5) . . ? O3 C39 C30 114.8(5) . . ? C38 C39 C30 119.1(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.596 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.107 # Attachment '(R)-2.CIF' data_y1 _database_code_depnum_ccdc_archive 'CCDC 806284' #TrackingRef '(R)-2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H18 N4 O2, C4 H8 O2, C3 H7 N O ' _chemical_formula_sum 'C33 H33 N5 O5' _chemical_formula_weight 579.64 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 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2610(3) _cell_length_b 16.4271(5) _cell_length_c 19.8316(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3017.01(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9065 _cell_measurement_theta_min 2.2186 _cell_measurement_theta_max 66.7806 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77318 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22393 _diffrn_reflns_av_R_equivalents 0.1015 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 24.98 _reflns_number_total 5247 _reflns_number_gt 4562 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.1250P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3.2(16) _refine_ls_number_reflns 5247 _refine_ls_number_parameters 396 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1774 _refine_ls_wR_factor_gt 0.1703 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 O1 O 0.8640(3) 0.45878(12) -0.16412(9) 0.0649(6) Uani 1 1 d . . . H1A H 0.859(5) 0.498(3) -0.126(3) 0.109(15) Uiso 1 1 d . . . O2 O 1.1718(2) 0.3589(2) -0.24698(11) 0.0820(8) Uani 1 1 d . . . H2A H 1.176(5) 0.355(3) -0.210(2) 0.085(12) Uiso 1 1 d . . . N1 N 0.7609(3) 0.1361(2) 0.11649(12) 0.0694(7) Uani 1 1 d . . . N2 N 0.8754(2) 0.13784(15) 0.01902(10) 0.0526(5) Uani 1 1 d . . . N3 N 0.6883(2) 0.34930(14) -0.47657(10) 0.0531(5) Uani 1 1 d . . . N4 N 0.6946(3) 0.42059(16) -0.57003(12) 0.0648(7) Uani 1 1 d . . . C1 C 0.7483(3) 0.1423(3) 0.05156(15) 0.0718(9) Uani 1 1 d . . . H1C H 0.6584 0.1492 0.0292 0.086 Uiso 1 1 calc R . . C2 C 0.9034(4) 0.1263(3) 0.12735(15) 0.0850(12) Uani 1 1 d . . . H2B H 0.9470 0.1196 0.1704 0.102 Uiso 1 1 calc R . . C3 C 0.9757(4) 0.1274(3) 0.06783(17) 0.0904(13) Uani 1 1 d . . . H3A H 1.0770 0.1219 0.0616 0.108 Uiso 1 1 calc R . . C4 C 0.8997(3) 0.14819(18) -0.05147(12) 0.0513(6) Uani 1 1 d . . . C5 C 0.9237(4) 0.08178(19) -0.09130(15) 0.0662(8) Uani 1 1 d . . . H5A H 0.9254 0.0287 -0.0723 0.079 Uiso 1 1 calc R . . C6 C 0.9464(4) 0.0932(2) -0.16177(15) 0.0719(9) Uani 1 1 d . . . H6A H 0.9657 0.0476 -0.1898 0.086 Uiso 1 1 calc R . . C7 C 0.9405(3) 0.16882(17) -0.18905(12) 0.0568(7) Uani 1 1 d . . . H7A H 0.9543 0.1748 -0.2363 0.068 Uiso 1 1 calc R . . C8 C 0.9143(3) 0.23968(16) -0.14930(12) 0.0449(5) Uani 1 1 d . . . C9 C 0.8943(3) 0.22839(16) -0.07868(11) 0.0455(5) Uani 1 1 d . . . C10 C 0.8724(3) 0.29775(17) -0.03783(11) 0.0498(6) Uani 1 1 d . . . H10A H 0.8626 0.2916 0.0096 0.060 Uiso 1 1 calc R . . C11 C 0.8653(3) 0.37274(18) -0.06564(12) 0.0520(6) Uani 1 1 d . . . H11A H 0.8514 0.4187 -0.0373 0.062 Uiso 1 1 calc R . . C12 C 0.8781(3) 0.38409(16) -0.13664(12) 0.0486(6) Uani 1 1 d . . . C13 C 0.9039(3) 0.31816(16) -0.17790(11) 0.0431(5) Uani 1 1 d . . . C14 C 0.9168(3) 0.33057(14) -0.25244(11) 0.0428(5) Uani 1 1 d . . . C15 C 1.0476(3) 0.35037(18) -0.28118(11) 0.0504(6) Uani 1 1 d . . . C16 C 1.0590(3) 0.36254(19) -0.35178(12) 0.0529(6) Uani 1 1 d . . . H16A H 1.1503 0.3751 -0.3709 0.064 Uiso 1 1 calc R . . C17 C 0.9424(3) 0.35655(17) -0.39221(11) 0.0493(6) Uani 1 1 d . . . H17A H 0.9526 0.3653 -0.4393 0.059 Uiso 1 1 calc R . . C18 C 0.8056(3) 0.33748(14) -0.36549(11) 0.0448(5) Uani 1 1 d . . . C19 C 0.7927(3) 0.32406(15) -0.29457(11) 0.0448(5) Uani 1 1 d . . . C20 C 0.6542(3) 0.3035(2) -0.26812(13) 0.0602(7) Uani 1 1 d . . . H20A H 0.6444 0.2930 -0.2212 0.072 Uiso 1 1 calc R . . C21 C 0.5367(4) 0.2986(3) -0.30824(17) 0.0785(10) Uani 1 1 d . . . H21A H 0.4458 0.2848 -0.2893 0.094 Uiso 1 1 calc R . . C22 C 0.5476(4) 0.3139(3) -0.37827(16) 0.0723(9) Uani 1 1 d . . . H22A H 0.4643 0.3114 -0.4062 0.087 Uiso 1 1 calc R . . C23 C 0.6791(3) 0.33234(16) -0.40517(12) 0.0523(6) Uani 1 1 d . . . C24 C 0.6865(4) 0.2952(2) -0.52828(15) 0.0717(9) Uani 1 1 d . . . H24A H 0.6834 0.2375 -0.5252 0.086 Uiso 1 1 calc R . . C25 C 0.6901(4) 0.3407(2) -0.58531(14) 0.0722(9) Uani 1 1 d . . . H25A H 0.6896 0.3193 -0.6298 0.087 Uiso 1 1 calc R . . C26 C 0.6928(4) 0.42293(19) -0.50442(14) 0.0630(7) Uani 1 1 d . . . H26A H 0.6945 0.4720 -0.4791 0.076 Uiso 1 1 calc R . . N5 N 1.2212(4) 0.4159(2) -0.59622(15) 0.0767(8) Uani 1 1 d . . . O3 O 1.2427(4) 0.4133(2) -0.48344(15) 0.1090(10) Uani 1 1 d . . . C27 C 1.2937(5) 0.4188(3) -0.54022(19) 0.0877(11) Uani 1 1 d . . . H27A H 1.3953 0.4258 -0.5436 0.105 Uiso 1 1 calc R . . C28 C 1.0646(6) 0.4075(4) -0.5937(3) 0.1160(16) Uani 1 1 d . . . H28A H 1.0335 0.4028 -0.5466 0.174 Uiso 1 1 calc R . . H28B H 1.0356 0.3586 -0.6186 0.174 Uiso 1 1 calc R . . H28C H 1.0195 0.4555 -0.6142 0.174 Uiso 1 1 calc R . . C29 C 1.2855(7) 0.4216(5) -0.6621(2) 0.1206(18) Uani 1 1 d . . . H29A H 1.3906 0.4256 -0.6576 0.181 Uiso 1 1 calc R . . H29B H 1.2487 0.4701 -0.6852 0.181 Uiso 1 1 calc R . . H29C H 1.2610 0.3730 -0.6883 0.181 Uiso 1 1 calc R . . O4 O 0.8973(5) 0.4231(3) -0.89978(17) 0.1294(14) Uani 1 1 d . . . O5 O 0.9717(7) 0.4147(6) -0.7666(2) 0.206(3) Uani 1 1 d . . . C30 C 1.0347(7) 0.4408(5) -0.8786(3) 0.135(2) Uani 1 1 d . . . H30A H 1.0797 0.4794 -0.9106 0.163 Uiso 1 1 calc R . . H30B H 1.0930 0.3903 -0.8785 0.163 Uiso 1 1 calc R . . C31 C 1.0361(13) 0.4758(6) -0.8121(5) 0.207(5) Uani 1 1 d . . . H31A H 1.1363 0.4883 -0.7981 0.249 Uiso 1 1 calc R . . H31B H 0.9791 0.5267 -0.8112 0.249 Uiso 1 1 calc R . . C32 C 0.8339(9) 0.4037(7) -0.7872(3) 0.175(4) Uani 1 1 d . . . H32A H 0.7837 0.4568 -0.7898 0.210 Uiso 1 1 calc R . . H32B H 0.7817 0.3688 -0.7546 0.210 Uiso 1 1 calc R . . C33 C 0.8358(10) 0.3666(6) -0.8509(4) 0.156(3) Uani 1 1 d . . . H33A H 0.8944 0.3162 -0.8492 0.187 Uiso 1 1 calc R . . H33B H 0.7363 0.3518 -0.8645 0.187 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 O1 0.1028(16) 0.0536(11) 0.0382(9) -0.0008(8) 0.0054(9) 0.0126(10) O2 0.0599(12) 0.151(3) 0.0353(9) 0.0095(13) -0.0050(9) -0.0197(14) N1 0.0685(15) 0.097(2) 0.0428(12) 0.0114(12) 0.0154(11) 0.0002(14) N2 0.0560(12) 0.0619(13) 0.0400(10) 0.0117(9) 0.0057(9) -0.0012(10) N3 0.0672(13) 0.0541(12) 0.0379(10) 0.0025(9) -0.0103(9) 0.0034(10) N4 0.0917(18) 0.0613(14) 0.0415(12) 0.0079(10) -0.0047(11) 0.0060(14) C1 0.0551(15) 0.113(3) 0.0475(14) 0.0193(16) 0.0087(12) 0.0057(17) C2 0.074(2) 0.141(4) 0.0400(13) 0.0131(18) -0.0061(14) -0.011(2) C3 0.0589(18) 0.160(4) 0.0523(17) 0.020(2) 0.0010(13) 0.001(2) C4 0.0566(13) 0.0615(15) 0.0358(11) 0.0087(11) 0.0067(10) 0.0010(13) C5 0.095(2) 0.0532(16) 0.0507(15) 0.0073(12) 0.0111(15) 0.0006(15) C6 0.112(3) 0.0581(17) 0.0461(15) -0.0045(13) 0.0148(16) 0.0023(17) C7 0.0825(18) 0.0558(16) 0.0321(11) -0.0010(10) 0.0086(11) 0.0000(13) C8 0.0484(13) 0.0537(14) 0.0324(11) 0.0003(10) 0.0016(9) -0.0019(11) C9 0.0458(12) 0.0582(14) 0.0324(11) 0.0020(10) 0.0026(9) -0.0016(11) C10 0.0549(13) 0.0650(16) 0.0295(10) 0.0014(11) 0.0038(9) -0.0041(12) C11 0.0621(15) 0.0621(16) 0.0317(11) -0.0055(10) 0.0010(10) 0.0025(12) C12 0.0579(14) 0.0531(14) 0.0347(11) -0.0008(10) 0.0007(10) 0.0003(11) C13 0.0482(12) 0.0530(13) 0.0281(10) 0.0006(9) 0.0018(9) -0.0011(10) C14 0.0584(13) 0.0427(12) 0.0273(10) 0.0007(8) 0.0000(10) 0.0035(10) C15 0.0576(14) 0.0635(15) 0.0302(11) -0.0008(11) -0.0014(10) -0.0044(12) C16 0.0559(14) 0.0683(16) 0.0346(11) 0.0022(11) 0.0060(10) -0.0034(13) C17 0.0699(16) 0.0517(13) 0.0262(9) 0.0033(9) 0.0027(10) 0.0006(12) C18 0.0624(14) 0.0396(12) 0.0324(10) 0.0014(9) -0.0038(10) 0.0012(10) C19 0.0583(14) 0.0429(12) 0.0333(11) 0.0004(9) 0.0020(10) 0.0008(10) C20 0.0616(15) 0.0778(19) 0.0412(12) 0.0095(13) 0.0009(11) -0.0063(14) C21 0.0605(18) 0.118(3) 0.0573(17) 0.0186(18) -0.0016(14) -0.0158(18) C22 0.0668(19) 0.097(2) 0.0526(16) 0.0100(16) -0.0145(14) -0.0063(17) C23 0.0660(16) 0.0530(14) 0.0379(12) 0.0053(10) -0.0095(11) -0.0001(12) C24 0.114(3) 0.0551(17) 0.0462(14) -0.0043(13) -0.0108(16) 0.0043(17) C25 0.109(3) 0.069(2) 0.0378(13) 0.0004(13) -0.0080(15) 0.0092(18) C26 0.095(2) 0.0521(15) 0.0416(13) 0.0039(11) -0.0050(13) 0.0036(15) N5 0.0856(19) 0.0865(19) 0.0579(15) -0.0055(13) 0.0147(14) -0.0060(16) O3 0.141(3) 0.119(2) 0.0670(16) 0.0051(15) 0.0206(17) -0.012(2) C27 0.093(2) 0.106(3) 0.064(2) -0.0029(19) 0.0059(19) -0.013(2) C28 0.114(4) 0.127(4) 0.108(4) 0.008(3) 0.007(3) -0.019(3) C29 0.131(4) 0.163(5) 0.068(2) -0.018(3) 0.022(3) -0.006(4) O4 0.128(3) 0.190(4) 0.0704(18) 0.014(2) -0.0034(18) -0.016(3) O5 0.177(5) 0.357(10) 0.084(3) 0.062(4) -0.017(3) 0.030(6) C30 0.119(4) 0.197(7) 0.091(3) 0.042(4) 0.003(3) -0.014(4) C31 0.281(13) 0.162(7) 0.180(8) 0.005(7) -0.105(9) -0.036(8) C32 0.139(6) 0.303(13) 0.082(4) 0.016(5) 0.021(4) 0.012(6) C33 0.163(6) 0.165(6) 0.139(6) -0.013(5) 0.026(5) -0.021(5) _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 C12 1.349(3) . ? O1 H1A 1.00(5) . ? O2 C15 1.343(3) . ? O2 H2A 0.74(5) . ? N1 C1 1.297(4) . ? N1 C2 1.348(5) . ? N2 C1 1.344(4) . ? N2 C3 1.352(4) . ? N2 C4 1.426(3) . ? N3 C26 1.330(4) . ? N3 C24 1.357(4) . ? N3 C23 1.446(3) . ? N4 C26 1.302(4) . ? N4 C25 1.347(5) . ? C1 H1C 0.9500 . ? C2 C3 1.357(5) . ? C2 H2B 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.365(4) . ? C4 C9 1.425(4) . ? C5 C6 1.426(4) . ? C5 H5A 0.9500 . ? C6 C7 1.356(4) . ? C6 H6A 0.9500 . ? C7 C8 1.427(4) . ? C7 H7A 0.9500 . ? C8 C13 1.412(4) . ? C8 C9 1.425(3) . ? C9 C10 1.413(4) . ? C10 C11 1.351(4) . ? C10 H10A 0.9500 . ? C11 C12 1.425(3) . ? C11 H11A 0.9500 . ? C12 C13 1.378(4) . ? C13 C14 1.497(3) . ? C14 C15 1.378(4) . ? C14 C19 1.424(4) . ? C15 C16 1.418(3) . ? C16 C17 1.348(4) . ? C16 H16A 0.9500 . ? C17 C18 1.408(4) . ? C17 H17A 0.9500 . ? C18 C23 1.414(4) . ? C18 C19 1.429(3) . ? C19 C20 1.427(4) . ? C20 C21 1.350(4) . ? C20 H20A 0.9500 . ? C21 C22 1.415(4) . ? C21 H21A 0.9500 . ? C22 C23 1.363(5) . ? C22 H22A 0.9500 . ? C24 C25 1.356(4) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? N5 C27 1.299(5) . ? N5 C29 1.438(5) . ? N5 C28 1.458(7) . ? O3 C27 1.225(5) . ? C27 H27A 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? O4 C30 1.371(7) . ? O4 C33 1.459(9) . ? O5 C32 1.352(10) . ? O5 C31 1.475(11) . ? C30 C31 1.439(10) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.403(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? 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 C12 O1 H1A 107(3) . . ? C15 O2 H2A 123(3) . . ? C1 N1 C2 104.8(2) . . ? C1 N2 C3 105.3(2) . . ? C1 N2 C4 127.0(2) . . ? C3 N2 C4 127.5(2) . . ? C26 N3 C24 106.4(2) . . ? C26 N3 C23 125.7(2) . . ? C24 N3 C23 127.8(2) . . ? C26 N4 C25 104.7(3) . . ? N1 C1 N2 113.2(3) . . ? N1 C1 H1C 123.4 . . ? N2 C1 H1C 123.4 . . ? N1 C2 C3 110.0(3) . . ? N1 C2 H2B 125.0 . . ? C3 C2 H2B 125.0 . . ? N2 C3 C2 106.6(3) . . ? N2 C3 H3A 126.7 . . ? C2 C3 H3A 126.7 . . ? C5 C4 N2 119.8(3) . . ? C5 C4 C9 121.7(2) . . ? N2 C4 C9 118.4(2) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5A 120.5 . . ? C6 C5 H5A 120.5 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 122.3(2) . . ? C6 C7 H7A 118.9 . . ? C8 C7 H7A 118.9 . . ? C13 C8 C9 120.3(2) . . ? C13 C8 C7 122.3(2) . . ? C9 C8 C7 117.3(2) . . ? C10 C9 C8 118.5(2) . . ? C10 C9 C4 122.3(2) . . ? C8 C9 C4 119.2(2) . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 121.2(2) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? O1 C12 C13 119.5(2) . . ? O1 C12 C11 120.7(2) . . ? C13 C12 C11 119.9(2) . . ? C12 C13 C8 119.4(2) . . ? C12 C13 C14 119.5(2) . . ? C8 C13 C14 121.0(2) . . ? C15 C14 C19 118.9(2) . . ? C15 C14 C13 120.7(2) . . ? C19 C14 C13 120.3(2) . . ? O2 C15 C14 124.7(2) . . ? O2 C15 C16 114.8(2) . . ? C14 C15 C16 120.5(2) . . ? C17 C16 C15 121.1(2) . . ? C17 C16 H16A 119.4 . . ? C15 C16 H16A 119.4 . . ? C16 C17 C18 120.8(2) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C23 C18 C17 123.3(2) . . ? C23 C18 C19 118.0(2) . . ? C17 C18 C19 118.7(2) . . ? C14 C19 C18 119.9(2) . . ? C14 C19 C20 121.8(2) . . ? C18 C19 C20 118.3(2) . . ? C21 C20 C19 121.5(2) . . ? C21 C20 H20A 119.3 . . ? C19 C20 H20A 119.3 . . ? C20 C21 C22 120.7(3) . . ? C20 C21 H21A 119.6 . . ? C22 C21 H21A 119.6 . . ? C23 C22 C21 119.1(3) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? C22 C23 C18 122.4(2) . . ? C22 C23 N3 118.6(2) . . ? C18 C23 N3 119.0(2) . . ? N3 C24 C25 105.6(3) . . ? N3 C24 H24A 127.2 . . ? C25 C24 H24A 127.2 . . ? N4 C25 C24 110.5(3) . . ? N4 C25 H25A 124.8 . . ? C24 C25 H25A 124.8 . . ? N4 C26 N3 112.9(3) . . ? N4 C26 H26A 123.6 . . ? N3 C26 H26A 123.6 . . ? C27 N5 C29 124.1(4) . . ? C27 N5 C28 119.2(4) . . ? C29 N5 C28 116.7(4) . . ? O3 C27 N5 125.7(4) . . ? O3 C27 H27A 117.1 . . ? N5 C27 H27A 117.1 . . ? N5 C28 H28A 109.5 . . ? N5 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N5 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C29 H29A 109.5 . . ? N5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 O4 C33 107.1(5) . . ? C32 O5 C31 106.8(6) . . ? O4 C30 C31 112.0(7) . . ? O4 C30 H30A 109.2 . . ? C31 C30 H30A 109.2 . . ? O4 C30 H30B 109.2 . . ? C31 C30 H30B 109.2 . . ? H30A C30 H30B 107.9 . . ? O5 C31 C30 106.5(7) . . ? O5 C31 H31A 110.4 . . ? C30 C31 H31A 110.4 . . ? O5 C31 H31B 110.4 . . ? C30 C31 H31B 110.4 . . ? H31A C31 H31B 108.6 . . ? O5 C32 C33 108.5(7) . . ? O5 C32 H32A 110.0 . . ? C33 C32 H32A 110.0 . . ? O5 C32 H32B 110.0 . . ? C33 C32 H32B 110.0 . . ? H32A C32 H32B 108.4 . . ? O4 C33 C32 109.1(7) . . ? O4 C33 H33A 109.9 . . ? C32 C33 H33A 109.9 . . ? O4 C33 H33B 109.9 . . ? C32 C33 H33B 109.9 . . ? H33A C33 H33B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.331 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.053 # Attachment '(R)-3.CIF' data_r1m _database_code_depnum_ccdc_archive 'CCDC 806285' #TrackingRef '(R)-3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H18 N4 O2' _chemical_formula_sum 'C26 H18 N4 O2' _chemical_formula_weight 418.44 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43' _symmetry_int_tables_number 78 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 11.950(2) _cell_length_b 11.950(2) _cell_length_c 21.080(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3010.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6422 _cell_measurement_theta_min 2.404 _cell_measurement_theta_max 25.961 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 13487 _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.07 _reflns_number_total 5400 _reflns_number_gt 4481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1500P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(18) _refine_ls_number_reflns 5400 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2197 _refine_ls_wR_factor_gt 0.2107 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.003 _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 O1 O 0.2572(2) 1.59162(18) -0.18542(10) 0.0546(6) Uani 1 1 d . . . H1A H 0.2479 1.5896 -0.1469 0.082 Uiso 1 1 calc R . . O2 O 0.43347(18) 1.4324(2) -0.08125(10) 0.0496(5) Uani 1 1 d . . . H2A H 0.489(7) 1.443(6) -0.053(4) 0.15(3) Uiso 1 1 d . . . N1 N 0.2731(3) 0.9561(2) -0.26499(14) 0.0538(7) Uani 1 1 d . . . N2 N 0.2689(3) 0.7734(3) -0.26651(19) 0.0746(10) Uani 1 1 d . . . N3 N -0.2020(2) 1.4360(2) -0.00106(12) 0.0476(6) Uani 1 1 d . . . N4 N -0.3873(2) 1.4553(3) -0.00365(14) 0.0607(8) Uani 1 1 d . . . C1 C 0.2983(7) 0.9211(4) -0.3248(2) 0.116(2) Uani 1 1 d . . . H1B H 0.3194 0.9655 -0.3590 0.139 Uiso 1 1 calc R . . C2 C 0.2866(6) 0.8103(4) -0.3242(3) 0.1006(19) Uani 1 1 d . . . H2C H 0.2905 0.7651 -0.3600 0.121 Uiso 1 1 calc R . . C3 C 0.2651(5) 0.8621(3) -0.2330(2) 0.0773(13) Uani 1 1 d . . . H3A H 0.2572 0.8604 -0.1892 0.093 Uiso 1 1 calc R . . C4 C 0.2688(3) 1.0691(2) -0.24149(15) 0.0482(7) Uani 1 1 d . . . C5 C 0.2552(4) 1.0859(3) -0.17660(17) 0.0610(9) Uani 1 1 d . . . H5A H 0.2481 1.0246 -0.1497 0.073 Uiso 1 1 calc R . . C6 C 0.2521(3) 1.1926(3) -0.15191(15) 0.0527(8) Uani 1 1 d . . . H6A H 0.2436 1.2026 -0.1084 0.063 Uiso 1 1 calc R . . C7 C 0.2617(2) 1.2874(2) -0.19207(14) 0.0370(6) Uani 1 1 d . . . C8 C 0.2762(2) 1.2689(2) -0.25785(13) 0.0360(6) Uani 1 1 d . . . C9 C 0.2805(3) 1.1589(2) -0.28187(15) 0.0449(7) Uani 1 1 d . . . H9A H 0.2912 1.1469 -0.3250 0.054 Uiso 1 1 calc R . . C10 C 0.2870(3) 1.3625(2) -0.29752(13) 0.0414(6) Uani 1 1 d . . . H10A H 0.2976 1.3520 -0.3408 0.050 Uiso 1 1 calc R . . C11 C 0.2823(3) 1.4678(2) -0.27402(13) 0.0421(6) Uani 1 1 d . . . H11A H 0.2900 1.5287 -0.3012 0.050 Uiso 1 1 calc R . . C12 C 0.2657(2) 1.4860(2) -0.20816(13) 0.0371(6) Uani 1 1 d . . . C13 C 0.2572(2) 1.3977(2) -0.16669(12) 0.0344(6) Uani 1 1 d . . . C14 C 0.2397(2) 1.4163(2) -0.09780(12) 0.0355(6) Uani 1 1 d . . . C15 C 0.3278(2) 1.4323(2) -0.05695(13) 0.0372(6) Uani 1 1 d . . . C16 C 0.3090(2) 1.4488(3) 0.00831(14) 0.0439(7) Uani 1 1 d . . . H16A H 0.3699 1.4582 0.0353 0.053 Uiso 1 1 calc R . . C17 C 0.2030(2) 1.4515(3) 0.03287(14) 0.0457(7) Uani 1 1 d . . . H17A H 0.1924 1.4638 0.0760 0.055 Uiso 1 1 calc R . . C18 C 0.1093(2) 1.4355(2) -0.00756(13) 0.0400(6) Uani 1 1 d . . . C19 C 0.1283(2) 1.4167(2) -0.07246(13) 0.0377(6) Uani 1 1 d . . . C20 C 0.0343(3) 1.3983(4) -0.11244(15) 0.0584(9) Uani 1 1 d . . . H20A H 0.0447 1.3837 -0.1554 0.070 Uiso 1 1 calc R . . C21 C -0.0724(3) 1.4022(4) -0.08757(16) 0.0635(10) Uani 1 1 d . . . H21A H -0.1334 1.3885 -0.1138 0.076 Uiso 1 1 calc R . . C22 C -0.0898(2) 1.4261(3) -0.02398(15) 0.0480(7) Uani 1 1 d . . . C23 C -0.0012(2) 1.4412(3) 0.01628(14) 0.0441(7) Uani 1 1 d . . . H23A H -0.0136 1.4551 0.0591 0.053 Uiso 1 1 calc R . . C24 C -0.2393(3) 1.4466(4) 0.05999(17) 0.0595(9) Uani 1 1 d . . . H24A H -0.1957 1.4443 0.0965 0.071 Uiso 1 1 calc R . . C25 C -0.3499(3) 1.4607(3) 0.05749(18) 0.0580(9) Uani 1 1 d . . . H25A H -0.3955 1.4727 0.0926 0.070 Uiso 1 1 calc R . . C26 C -0.2952(3) 1.4429(4) -0.03769(17) 0.0628(10) Uani 1 1 d . . . H26A H -0.2944 1.4393 -0.0818 0.075 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 O1 0.0893(17) 0.0367(11) 0.0377(12) -0.0085(8) 0.0029(11) 0.0010(10) O2 0.0344(10) 0.0729(15) 0.0414(12) -0.0030(10) 0.0036(9) -0.0019(9) N1 0.0780(19) 0.0381(13) 0.0453(15) -0.0016(11) 0.0009(13) 0.0034(12) N2 0.095(3) 0.0419(16) 0.086(3) -0.0017(16) 0.0044(19) -0.0007(15) N3 0.0339(12) 0.0684(17) 0.0404(15) -0.0042(11) 0.0057(10) 0.0038(11) N4 0.0391(14) 0.091(2) 0.0525(18) -0.0044(15) 0.0010(12) 0.0046(13) C1 0.253(8) 0.045(2) 0.049(2) -0.0025(18) 0.015(3) 0.003(3) C2 0.188(6) 0.045(2) 0.069(3) -0.012(2) -0.007(3) 0.008(3) C3 0.129(4) 0.0410(19) 0.062(2) 0.0021(16) 0.021(2) 0.0038(19) C4 0.067(2) 0.0322(14) 0.0455(17) -0.0012(12) 0.0047(14) 0.0028(12) C5 0.100(3) 0.0386(16) 0.0446(19) 0.0075(13) 0.0065(17) 0.0010(16) C6 0.078(2) 0.0454(17) 0.0344(17) 0.0049(12) 0.0102(14) -0.0023(14) C7 0.0363(13) 0.0364(13) 0.0384(15) -0.0005(10) 0.0056(10) 0.0017(10) C8 0.0420(14) 0.0347(13) 0.0314(14) -0.0001(10) 0.0045(10) 0.0039(10) C9 0.0551(17) 0.0382(15) 0.0413(16) -0.0014(11) 0.0043(12) 0.0022(11) C10 0.0527(16) 0.0469(16) 0.0245(13) 0.0018(11) 0.0046(11) -0.0011(12) C11 0.0627(18) 0.0320(13) 0.0315(14) 0.0033(10) 0.0018(12) -0.0012(11) C12 0.0375(13) 0.0361(13) 0.0376(15) -0.0019(11) 0.0008(10) -0.0003(10) C13 0.0305(12) 0.0399(14) 0.0328(14) -0.0010(11) -0.0006(9) 0.0003(9) C14 0.0393(13) 0.0364(13) 0.0309(14) -0.0006(10) 0.0057(11) 0.0035(10) C15 0.0329(13) 0.0414(14) 0.0373(15) -0.0018(11) 0.0026(10) 0.0000(10) C16 0.0379(14) 0.0597(18) 0.0342(16) -0.0015(12) -0.0057(11) -0.0027(12) C17 0.0439(16) 0.0665(18) 0.0265(14) -0.0052(12) -0.0005(11) 0.0012(13) C18 0.0390(14) 0.0484(15) 0.0325(14) 0.0002(11) 0.0024(11) -0.0006(11) C19 0.0358(13) 0.0420(14) 0.0353(15) -0.0050(11) -0.0025(11) 0.0027(10) C20 0.0472(17) 0.101(3) 0.0269(15) -0.0095(15) 0.0011(12) 0.0024(16) C21 0.0372(16) 0.114(3) 0.0395(18) -0.0172(18) -0.0068(13) -0.0027(16) C22 0.0277(13) 0.0667(19) 0.0495(18) -0.0032(14) 0.0055(12) 0.0036(12) C23 0.0382(14) 0.0658(18) 0.0281(14) -0.0042(12) 0.0031(11) 0.0007(12) C24 0.0422(16) 0.097(3) 0.0391(17) -0.0059(16) 0.0021(13) 0.0060(16) C25 0.0421(16) 0.079(2) 0.053(2) -0.0102(16) 0.0106(14) -0.0009(15) C26 0.0361(16) 0.109(3) 0.0432(19) -0.0091(18) -0.0049(13) 0.0030(16) _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 C12 1.354(3) . ? O1 H1A 0.8200 . ? O2 C15 1.362(3) . ? O2 H2A 0.90(9) . ? N1 C3 1.314(5) . ? N1 C1 1.363(6) . ? N1 C4 1.439(4) . ? N2 C3 1.274(5) . ? N2 C2 1.312(7) . ? N3 C26 1.358(4) . ? N3 C24 1.368(4) . ? N3 C22 1.430(4) . ? N4 C26 1.322(5) . ? N4 C25 1.365(5) . ? C1 C2 1.331(6) . ? C1 H1B 0.9300 . ? C2 H2C 0.9300 . ? C3 H3A 0.9300 . ? C4 C9 1.377(4) . ? C4 C5 1.392(5) . ? C5 C6 1.378(5) . ? C5 H5A 0.9300 . ? C6 C7 1.419(4) . ? C6 H6A 0.9300 . ? C7 C8 1.415(4) . ? C7 C13 1.424(4) . ? C8 C10 1.403(4) . ? C8 C9 1.410(4) . ? C9 H9A 0.9300 . ? C10 C11 1.354(4) . ? C10 H10A 0.9300 . ? C11 C12 1.419(4) . ? C11 H11A 0.9300 . ? C12 C13 1.374(4) . ? C13 C14 1.484(3) . ? C14 C15 1.374(4) . ? C14 C19 1.434(4) . ? C15 C16 1.408(4) . ? C16 C17 1.369(4) . ? C16 H16A 0.9300 . ? C17 C18 1.420(4) . ? C17 H17A 0.9300 . ? C18 C19 1.405(4) . ? C18 C23 1.415(4) . ? C19 C20 1.422(4) . ? C20 C21 1.379(5) . ? C20 H20A 0.9300 . ? C21 C22 1.386(5) . ? C21 H21A 0.9300 . ? C22 C23 1.369(4) . ? C23 H23A 0.9300 . ? C24 C25 1.333(5) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? 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 C12 O1 H1A 109.5 . . ? C15 O2 H2A 116(6) . . ? C3 N1 C1 103.2(3) . . ? C3 N1 C4 128.6(3) . . ? C1 N1 C4 127.9(3) . . ? C3 N2 C2 103.9(3) . . ? C26 N3 C24 105.2(3) . . ? C26 N3 C22 125.6(3) . . ? C24 N3 C22 129.1(3) . . ? C26 N4 C25 104.2(3) . . ? C2 C1 N1 105.9(4) . . ? C2 C1 H1B 127.1 . . ? N1 C1 H1B 127.1 . . ? N2 C2 C1 111.1(4) . . ? N2 C2 H2C 124.4 . . ? C1 C2 H2C 124.4 . . ? N2 C3 N1 115.2(4) . . ? N2 C3 H3A 122.4 . . ? N1 C3 H3A 122.4 . . ? C9 C4 C5 120.5(3) . . ? C9 C4 N1 121.0(3) . . ? C5 C4 N1 118.5(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C8 C7 C6 118.0(2) . . ? C8 C7 C13 121.2(2) . . ? C6 C7 C13 120.8(3) . . ? C10 C8 C9 121.7(3) . . ? C10 C8 C7 118.1(2) . . ? C9 C8 C7 120.1(2) . . ? C4 C9 C8 120.1(3) . . ? C4 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C11 C10 C8 121.3(3) . . ? C11 C10 H10A 119.4 . . ? C8 C10 H10A 119.4 . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? O1 C12 C13 119.0(2) . . ? O1 C12 C11 120.0(2) . . ? C13 C12 C11 121.0(2) . . ? C12 C13 C7 118.0(2) . . ? C12 C13 C14 121.2(2) . . ? C7 C13 C14 120.8(2) . . ? C15 C14 C19 118.5(2) . . ? C15 C14 C13 121.7(2) . . ? C19 C14 C13 119.7(2) . . ? O2 C15 C14 118.4(2) . . ? O2 C15 C16 121.0(2) . . ? C14 C15 C16 120.6(2) . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16A 119.3 . . ? C15 C16 H16A 119.3 . . ? C16 C17 C18 120.0(3) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C19 C18 C23 120.3(3) . . ? C19 C18 C17 118.6(2) . . ? C23 C18 C17 121.1(3) . . ? C18 C19 C20 118.3(3) . . ? C18 C19 C14 120.9(2) . . ? C20 C19 C14 120.8(3) . . ? C21 C20 C19 120.0(3) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C20 C21 C22 120.9(3) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C23 C22 C21 120.7(3) . . ? C23 C22 N3 120.3(3) . . ? C21 C22 N3 119.0(3) . . ? C22 C23 C18 119.7(3) . . ? C22 C23 H23A 120.1 . . ? C18 C23 H23A 120.1 . . ? C25 C24 N3 107.3(3) . . ? C25 C24 H24A 126.3 . . ? N3 C24 H24A 126.3 . . ? C24 C25 N4 110.8(3) . . ? C24 C25 H25A 124.6 . . ? N4 C25 H25A 124.6 . . ? N4 C26 N3 112.4(3) . . ? N4 C26 H26A 123.8 . . ? N3 C26 H26A 123.8 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.566 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.076 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.001 0.023 -0.004 1328 404 ' ' _platon_squeeze_details ; ;