# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_20121116b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 N4 O2' _chemical_formula_weight 424.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.251(4) _cell_length_b 11.0982(16) _cell_length_c 18.647(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.073(2) _cell_angle_gamma 90.00 _cell_volume 4428.1(11) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4741 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.77 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15760 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.45 _reflns_number_total 4091 _reflns_number_gt 3130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0696P)^2^+1.7782P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4091 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _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 C1 C 0.25614(7) -0.04689(15) 0.39764(9) 0.0427(4) Uani 1 1 d . . . C2 C 0.30143(8) -0.00746(17) 0.38156(11) 0.0550(5) Uani 1 1 d . . . C3 C 0.34402(9) -0.0907(2) 0.38561(13) 0.0675(6) Uani 1 1 d . . . H3 H 0.3746 -0.0651 0.3756 0.081 Uiso 1 1 calc R . . C4 C 0.34207(10) -0.2089(2) 0.40395(13) 0.0718(6) Uani 1 1 d . . . H4 H 0.3716 -0.2626 0.4073 0.086 Uiso 1 1 calc R . . C5 C 0.29659(10) -0.24875(18) 0.41747(13) 0.0669(5) Uani 1 1 d . . . H5 H 0.2943 -0.3298 0.4282 0.080 Uiso 1 1 calc R . . C6 C 0.25416(8) -0.16750(16) 0.41504(11) 0.0519(4) Uani 1 1 d . . . H6 H 0.2238 -0.1943 0.4252 0.062 Uiso 1 1 calc R . . C7 C 0.30349(10) 0.1219(2) 0.35878(16) 0.0779(7) Uani 1 1 d . . . H7A H 0.3467 0.1476 0.3869 0.093 Uiso 1 1 calc R . . H7B H 0.2855 0.1276 0.2982 0.093 Uiso 1 1 calc R . . C8 C 0.26876(9) 0.20488(18) 0.38328(16) 0.0747(6) Uani 1 1 d . . . H8A H 0.2944 0.2195 0.4437 0.090 Uiso 1 1 calc R . . H8B H 0.2628 0.2815 0.3549 0.090 Uiso 1 1 calc R . . C9 C 0.21379(7) 0.04434(14) 0.40409(10) 0.0425(4) Uani 1 1 d . . . H9 H 0.2334 0.0619 0.4645 0.051 Uiso 1 1 calc R . . C10 C 0.12180(7) -0.05655(14) 0.23886(9) 0.0385(4) Uani 1 1 d . . . C11 C 0.15435(8) 0.04724(15) 0.22557(10) 0.0479(4) Uani 1 1 d . . . H11A H 0.1955 0.0209 0.2399 0.057 Uiso 1 1 calc R . . H11B H 0.1309 0.0688 0.1661 0.057 Uiso 1 1 calc R . . C12 C 0.13024(8) -0.00224(16) 0.43015(10) 0.0504(4) Uani 1 1 d . . . C13 C 0.06769(10) -0.0579(2) 0.39809(13) 0.0749(6) Uani 1 1 d . . . H13A H 0.0584 -0.0558 0.4418 0.112 Uiso 1 1 calc R . . H13B H 0.0681 -0.1400 0.3822 0.112 Uiso 1 1 calc R . . H13C H 0.0364 -0.0137 0.3497 0.112 Uiso 1 1 calc R . . C14 C 0.08772(7) -0.14609(14) 0.16967(9) 0.0407(4) Uani 1 1 d . . . C15 C 0.07342(10) -0.12540(19) 0.08844(11) 0.0624(5) Uani 1 1 d . . . H15 H 0.0872 -0.0551 0.0762 0.075 Uiso 1 1 calc R . . C16 C 0.03874(11) -0.2084(2) 0.02483(13) 0.0798(7) Uani 1 1 d . . . H16 H 0.0288 -0.1925 -0.0299 0.096 Uiso 1 1 calc R . . C17 C 0.01924(9) -0.3118(2) 0.04117(15) 0.0780(7) Uani 1 1 d . . . H17 H -0.0045 -0.3664 -0.0022 0.094 Uiso 1 1 calc R . . C18 C 0.03456(10) -0.3363(2) 0.12184(16) 0.0758(6) Uani 1 1 d . . . H18 H 0.0220 -0.4085 0.1336 0.091 Uiso 1 1 calc R . . C19 C 0.06854(9) -0.25427(17) 0.18583(13) 0.0592(5) Uani 1 1 d . . . H19 H 0.0787 -0.2717 0.2405 0.071 Uiso 1 1 calc R . . C20 C 0.10908(8) 0.22167(17) 0.24950(10) 0.0525(4) Uani 1 1 d . . . C21 C 0.11352(8) 0.32434(16) 0.30423(10) 0.0497(4) Uani 1 1 d . . . C22 C 0.07737(10) 0.3233(2) 0.33955(15) 0.0713(6) Uani 1 1 d . . . H22 H 0.0526 0.2566 0.3322 0.086 Uiso 1 1 calc R . . C23 C 0.07781(13) 0.4205(2) 0.38556(17) 0.0864(7) Uani 1 1 d . . . H23 H 0.0536 0.4185 0.4096 0.104 Uiso 1 1 calc R . . C24 C 0.11309(11) 0.5198(2) 0.39650(14) 0.0766(6) Uani 1 1 d . . . H24 H 0.1126 0.5857 0.4269 0.092 Uiso 1 1 calc R . . C25 C 0.14923(11) 0.5209(2) 0.36200(14) 0.0792(6) Uani 1 1 d . . . H25 H 0.1735 0.5881 0.3691 0.095 Uiso 1 1 calc R . . C26 C 0.15006(10) 0.4228(2) 0.31649(13) 0.0696(6) Uani 1 1 d . . . H26 H 0.1755 0.4239 0.2943 0.084 Uiso 1 1 calc R . . N1 N 0.20763(6) 0.16019(12) 0.36292(9) 0.0513(4) Uani 1 1 d . . . N2 N 0.16119(6) 0.15422(12) 0.27534(8) 0.0472(3) Uani 1 1 d . . . N3 N 0.15194(6) -0.00310(12) 0.37594(8) 0.0427(3) Uani 1 1 d . . . N4 N 0.11800(6) -0.07510(12) 0.30395(8) 0.0414(3) Uani 1 1 d . . . O1 O 0.16085(6) 0.04439(14) 0.49956(8) 0.0692(4) Uani 1 1 d . . . O2 O 0.06118(7) 0.19939(17) 0.18253(9) 0.0923(6) 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 C1 0.0392(8) 0.0429(9) 0.0390(8) -0.0027(7) 0.0160(6) -0.0022(7) C2 0.0437(9) 0.0612(12) 0.0557(10) -0.0007(8) 0.0234(8) -0.0051(8) C3 0.0530(11) 0.0868(16) 0.0667(12) -0.0094(11) 0.0344(10) -0.0001(10) C4 0.0611(12) 0.0784(15) 0.0689(13) -0.0191(11) 0.0297(10) 0.0136(11) C5 0.0711(13) 0.0474(11) 0.0653(12) -0.0051(9) 0.0249(10) 0.0091(9) C6 0.0524(9) 0.0464(10) 0.0508(9) 0.0006(8) 0.0234(8) 0.0001(8) C7 0.0514(11) 0.0753(15) 0.1030(17) 0.0117(12) 0.0382(12) -0.0157(10) C8 0.0492(10) 0.0475(11) 0.0992(16) 0.0028(11) 0.0204(11) -0.0154(9) C9 0.0368(8) 0.0408(9) 0.0394(8) -0.0050(6) 0.0131(6) -0.0035(6) C10 0.0357(7) 0.0371(8) 0.0387(8) 0.0002(6) 0.0171(6) -0.0012(6) C11 0.0559(10) 0.0408(9) 0.0463(9) -0.0009(7) 0.0267(8) -0.0082(7) C12 0.0523(9) 0.0543(11) 0.0449(9) -0.0034(8) 0.0261(8) 0.0010(8) C13 0.0681(13) 0.1044(18) 0.0667(12) -0.0154(12) 0.0455(11) -0.0201(12) C14 0.0324(7) 0.0434(9) 0.0416(8) -0.0055(7) 0.0164(6) -0.0013(6) C15 0.0755(12) 0.0611(12) 0.0439(10) -0.0058(8) 0.0271(9) -0.0065(10) C16 0.0848(15) 0.0864(17) 0.0435(10) -0.0192(10) 0.0173(10) 0.0010(13) C17 0.0463(10) 0.0894(18) 0.0777(15) -0.0476(13) 0.0189(10) -0.0094(10) C18 0.0703(13) 0.0641(14) 0.1011(18) -0.0349(12) 0.0510(13) -0.0289(11) C19 0.0653(11) 0.0525(11) 0.0649(11) -0.0155(9) 0.0379(10) -0.0183(9) C20 0.0467(9) 0.0583(11) 0.0428(9) 0.0007(8) 0.0172(8) 0.0009(8) C21 0.0431(8) 0.0499(10) 0.0443(9) 0.0058(7) 0.0151(7) 0.0071(7) C22 0.0733(13) 0.0564(13) 0.0978(16) 0.0080(11) 0.0546(13) 0.0094(10) C23 0.1015(18) 0.0751(16) 0.1094(19) 0.0039(14) 0.0742(16) 0.0209(14) C24 0.0812(15) 0.0700(15) 0.0665(13) -0.0061(11) 0.0310(12) 0.0201(12) C25 0.0797(14) 0.0633(14) 0.0749(14) -0.0122(11) 0.0278(12) -0.0141(11) C26 0.0733(13) 0.0691(14) 0.0698(13) -0.0129(10) 0.0404(11) -0.0159(11) N1 0.0396(7) 0.0369(8) 0.0545(8) -0.0028(6) 0.0095(6) -0.0069(6) N2 0.0487(8) 0.0358(7) 0.0470(7) -0.0007(6) 0.0185(6) -0.0052(6) N3 0.0396(7) 0.0467(8) 0.0382(7) -0.0071(6) 0.0183(6) -0.0062(6) N4 0.0394(7) 0.0430(7) 0.0372(7) -0.0044(5) 0.0171(5) -0.0065(6) O1 0.0744(9) 0.0853(10) 0.0516(7) -0.0216(7) 0.0359(7) -0.0101(7) O2 0.0594(9) 0.1230(14) 0.0539(8) -0.0243(8) 0.0026(7) 0.0191(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 C1 C6 1.384(2) . ? C1 C2 1.398(2) . ? C1 C9 1.523(2) . ? C2 C3 1.389(3) . ? C2 C7 1.505(3) . ? C3 C4 1.363(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(3) . ? C4 H4 0.9300 . ? C5 C6 1.382(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.501(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.466(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N3 1.457(2) . ? C9 N1 1.463(2) . ? C9 H9 0.9800 . ? C10 N4 1.2840(19) . ? C10 C14 1.488(2) . ? C10 C11 1.510(2) . ? C11 N2 1.460(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O1 1.216(2) . ? C12 N3 1.382(2) . ? C12 C13 1.494(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.377(2) . ? C14 C19 1.386(2) . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 C17 1.346(4) . ? C16 H16 0.9300 . ? C17 C18 1.367(3) . ? C17 H17 0.9300 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O2 1.216(2) . ? C20 N2 1.361(2) . ? C20 C21 1.494(2) . ? C21 C26 1.369(3) . ? C21 C22 1.380(3) . ? C22 C23 1.375(3) . ? C22 H22 0.9300 . ? C23 C24 1.362(3) . ? C23 H23 0.9300 . ? C24 C25 1.367(3) . ? C24 H24 0.9300 . ? C25 C26 1.387(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N1 N2 1.4186(18) . ? N3 N4 1.3975(17) . ? 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 C6 C1 C2 119.24(16) . . ? C6 C1 C9 120.66(15) . . ? C2 C1 C9 119.84(15) . . ? C3 C2 C1 118.58(18) . . ? C3 C2 C7 120.49(18) . . ? C1 C2 C7 120.92(17) . . ? C4 C3 C2 121.6(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.08(19) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 120.96(18) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C8 C7 C2 112.70(18) . . ? C8 C7 H7A 109.1 . . ? C2 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C2 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C7 114.74(16) . . ? N1 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? N1 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? N3 C9 N1 109.50(12) . . ? N3 C9 C1 113.24(13) . . ? N1 C9 C1 115.23(14) . . ? N3 C9 H9 106.0 . . ? N1 C9 H9 106.0 . . ? C1 C9 H9 106.0 . . ? N4 C10 C14 114.43(13) . . ? N4 C10 C11 126.71(13) . . ? C14 C10 C11 118.80(13) . . ? N2 C11 C10 114.03(13) . . ? N2 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? N2 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O1 C12 N3 120.46(16) . . ? O1 C12 C13 122.78(16) . . ? N3 C12 C13 116.74(15) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 117.75(16) . . ? C15 C14 C10 122.38(15) . . ? C19 C14 C10 119.86(14) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 119.65(18) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 120.82(19) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? O2 C20 N2 119.95(17) . . ? O2 C20 C21 121.97(17) . . ? N2 C20 C21 118.05(14) . . ? C26 C21 C22 119.01(18) . . ? C26 C21 C20 121.50(17) . . ? C22 C21 C20 119.40(17) . . ? C23 C22 C21 120.2(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 121.1(2) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 118.9(2) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C24 C25 C26 120.8(2) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 120.0(2) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? N2 N1 C9 110.84(11) . . ? N2 N1 C8 115.26(16) . . ? C9 N1 C8 110.94(13) . . ? C20 N2 N1 115.77(13) . . ? C20 N2 C11 117.17(14) . . ? N1 N2 C11 121.09(13) . . ? C12 N3 N4 115.31(13) . . ? C12 N3 C9 119.97(13) . . ? N4 N3 C9 123.10(12) . . ? C10 N4 N3 120.06(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.5(2) . . . . ? C9 C1 C2 C3 172.72(15) . . . . ? C6 C1 C2 C7 177.41(17) . . . . ? C9 C1 C2 C7 -8.4(2) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C7 C2 C3 C4 -178.3(2) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -2.1(3) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? C9 C1 C6 C5 -173.57(15) . . . . ? C3 C2 C7 C8 -162.15(18) . . . . ? C1 C2 C7 C8 19.0(3) . . . . ? C2 C7 C8 N1 -44.2(3) . . . . ? C6 C1 C9 N3 -36.95(19) . . . . ? C2 C1 C9 N3 148.90(14) . . . . ? C6 C1 C9 N1 -164.11(13) . . . . ? C2 C1 C9 N1 21.75(19) . . . . ? N4 C10 C11 N2 -23.6(2) . . . . ? C14 C10 C11 N2 153.65(13) . . . . ? N4 C10 C14 C15 163.56(16) . . . . ? C11 C10 C14 C15 -14.0(2) . . . . ? N4 C10 C14 C19 -15.6(2) . . . . ? C11 C10 C14 C19 166.81(16) . . . . ? C19 C14 C15 C16 2.7(3) . . . . ? C10 C14 C15 C16 -176.57(18) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 -0.9(4) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C17 C18 C19 C14 0.0(3) . . . . ? C15 C14 C19 C18 -2.0(3) . . . . ? C10 C14 C19 C18 177.19(17) . . . . ? O2 C20 C21 C26 -112.1(2) . . . . ? N2 C20 C21 C26 66.1(2) . . . . ? O2 C20 C21 C22 64.3(3) . . . . ? N2 C20 C21 C22 -117.58(19) . . . . ? C26 C21 C22 C23 0.6(3) . . . . ? C20 C21 C22 C23 -175.8(2) . . . . ? C21 C22 C23 C24 0.7(4) . . . . ? C22 C23 C24 C25 -1.1(4) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C22 C21 C26 C25 -1.6(3) . . . . ? C20 C21 C26 C25 174.74(19) . . . . ? C24 C25 C26 C21 1.3(3) . . . . ? N3 C9 N1 N2 -44.99(17) . . . . ? C1 C9 N1 N2 84.04(16) . . . . ? N3 C9 N1 C8 -174.38(15) . . . . ? C1 C9 N1 C8 -45.35(19) . . . . ? C7 C8 N1 N2 -68.7(2) . . . . ? C7 C8 N1 C9 58.3(2) . . . . ? O2 C20 N2 N1 -160.99(17) . . . . ? C21 C20 N2 N1 20.8(2) . . . . ? O2 C20 N2 C11 -7.8(3) . . . . ? C21 C20 N2 C11 173.99(14) . . . . ? C9 N1 N2 C20 112.94(16) . . . . ? C8 N1 N2 C20 -120.00(18) . . . . ? C9 N1 N2 C11 -39.1(2) . . . . ? C8 N1 N2 C11 87.96(18) . . . . ? C10 C11 N2 C20 -74.55(19) . . . . ? C10 C11 N2 N1 77.12(19) . . . . ? O1 C12 N3 N4 170.33(16) . . . . ? C13 C12 N3 N4 -11.2(2) . . . . ? O1 C12 N3 C9 4.4(3) . . . . ? C13 C12 N3 C9 -177.09(17) . . . . ? N1 C9 N3 C12 -106.95(17) . . . . ? C1 C9 N3 C12 122.94(16) . . . . ? N1 C9 N3 N4 88.26(17) . . . . ? C1 C9 N3 N4 -41.85(19) . . . . ? C14 C10 N4 N3 174.97(12) . . . . ? C11 C10 N4 N3 -7.7(2) . . . . ? C12 N3 N4 C10 159.70(15) . . . . ? C9 N3 N4 C10 -34.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.228 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 940663' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H26 N4 O2' _chemical_formula_weight 486.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.667(3) _cell_length_b 27.905(7) _cell_length_c 9.770(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.429(5) _cell_angle_gamma 90.00 _cell_volume 2890.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1340 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 19.76 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9929 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5209 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.30 _reflns_number_total 5209 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1154P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5209 _refine_ls_number_parameters 365 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.1546 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2147 _refine_ls_wR_factor_gt 0.1831 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.922 _refine_ls_shift/su_max 0.000 _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 C1 C 0.4190(6) 0.94999(13) 0.3214(7) 0.054(5) Uani 0.67 1 d PGDU A 1 C2 C 0.3373(6) 0.97753(18) 0.3901(7) 0.076(2) Uani 0.67 1 d PGU A 1 H2 H 0.2920 0.9634 0.4554 0.091 Uiso 0.67 1 calc PR A 1 C3 C 0.3233(6) 1.02612(17) 0.3611(8) 0.090(3) Uani 0.67 1 d PGU A 1 H3 H 0.2686 1.0445 0.4070 0.108 Uiso 0.67 1 calc PR A 1 C4 C 0.3910(6) 1.04718(12) 0.2634(7) 0.099(3) Uani 0.67 1 d PGU A 1 H4 H 0.3816 1.0797 0.2440 0.119 Uiso 0.67 1 calc PR A 1 C5 C 0.4727(6) 1.01963(16) 0.1947(6) 0.111(3) Uani 0.67 1 d PGU A 1 H5 H 0.5180 1.0337 0.1293 0.133 Uiso 0.67 1 calc PR A 1 C6 C 0.4867(5) 0.97104(15) 0.2237(6) 0.079(2) Uani 0.67 1 d PGU A 1 H6 H 0.5414 0.9526 0.1777 0.095 Uiso 0.67 1 calc PR A 1 C7 C 0.4513(4) 0.89957(13) 0.3500(4) 0.0559(11) Uani 1 1 d D . . C1' C 0.4096(13) 0.9500(4) 0.308(2) 0.073(13) Uani 0.33 1 d PGDU A 2 C2' C 0.3885(16) 0.9792(6) 0.4183(15) 0.105(8) Uani 0.33 1 d PGU A 2 H2' H 0.4039 0.9677 0.5080 0.126 Uiso 0.33 1 calc PR A 2 C3' C 0.3444(16) 1.0257(6) 0.3947(16) 0.22(2) Uani 0.33 1 d PGU A 2 H3' H 0.3303 1.0453 0.4685 0.264 Uiso 0.33 1 calc PR A 2 C4' C 0.3214(14) 1.0429(3) 0.2608(19) 0.098(6) Uani 0.33 1 d PGU A 2 H4' H 0.2919 1.0740 0.2450 0.118 Uiso 0.33 1 calc PR A 2 C5' C 0.3425(15) 1.0137(5) 0.1505(14) 0.156(8) Uani 0.33 1 d PGU A 2 H5' H 0.3271 1.0252 0.0609 0.187 Uiso 0.33 1 calc PR A 2 C6' C 0.3865(14) 0.9672(4) 0.1741(17) 0.128(7) Uani 0.33 1 d PGU A 2 H6' H 0.4006 0.9477 0.1003 0.154 Uiso 0.33 1 calc PR A 2 C8 C 0.3851(3) 0.81860(12) 0.3864(4) 0.0476(10) Uani 1 1 d . . . H8 H 0.4628 0.8102 0.4330 0.057 Uiso 1 1 calc R A . C9 C 0.3044(3) 0.78359(12) 0.3435(4) 0.0414(9) Uani 1 1 d . A . C10 C 0.1790(3) 0.84647(12) 0.2160(4) 0.0431(9) Uani 1 1 d . A . H10 H 0.2274 0.8517 0.1378 0.052 Uiso 1 1 calc R . . C11 C 0.0447(3) 0.85967(13) 0.1693(4) 0.0484(10) Uani 1 1 d . . . C12 C -0.0279(4) 0.88299(13) 0.2582(5) 0.0559(11) Uani 1 1 d . . . C13 C 0.0309(4) 0.90094(16) 0.3948(4) 0.0633(12) Uani 1 1 d . . . H13A H -0.0271 0.8955 0.4629 0.076 Uiso 1 1 calc R . . H13B H 0.0439 0.9352 0.3886 0.076 Uiso 1 1 calc R . . C14 C 0.1558(4) 0.87721(13) 0.4431(4) 0.0524(10) Uani 1 1 d . A . H14A H 0.1988 0.8944 0.5210 0.063 Uiso 1 1 calc R . . H14B H 0.1427 0.8443 0.4706 0.063 Uiso 1 1 calc R . . C15 C -0.1536(4) 0.89193(16) 0.2155(6) 0.0821(15) Uani 1 1 d . . . H15 H -0.2039 0.9068 0.2749 0.099 Uiso 1 1 calc R . . C16 C -0.2047(5) 0.87883(19) 0.0845(8) 0.0995(19) Uani 1 1 d . . . H16 H -0.2896 0.8846 0.0564 0.119 Uiso 1 1 calc R . . C17 C -0.1313(5) 0.85749(18) -0.0042(7) 0.0979(19) Uani 1 1 d . . . H17 H -0.1656 0.8498 -0.0933 0.117 Uiso 1 1 calc R . . C18 C -0.0076(4) 0.84742(15) 0.0379(5) 0.0694(13) Uani 1 1 d . . . H18 H 0.0416 0.8323 -0.0219 0.083 Uiso 1 1 calc R . . C19 C 0.3351(3) 0.73330(12) 0.3748(4) 0.0378(8) Uani 1 1 d . . . C20 C 0.4070(3) 0.72134(13) 0.4968(4) 0.0473(9) Uani 1 1 d . A . H20 H 0.4284 0.7452 0.5615 0.057 Uiso 1 1 calc R . . C21 C 0.4479(4) 0.67534(15) 0.5254(4) 0.0557(11) Uani 1 1 d . . . H21 H 0.4985 0.6685 0.6069 0.067 Uiso 1 1 calc R A . C22 C 0.4127(4) 0.63915(14) 0.4314(5) 0.0623(12) Uani 1 1 d . A . H22 H 0.4387 0.6078 0.4502 0.075 Uiso 1 1 calc R . . C23 C 0.3398(4) 0.64979(14) 0.3107(5) 0.0635(12) Uani 1 1 d . . . H23 H 0.3155 0.6255 0.2482 0.076 Uiso 1 1 calc R A . C24 C 0.3022(3) 0.69617(13) 0.2815(4) 0.0484(9) Uani 1 1 d . A . H24 H 0.2543 0.7030 0.1983 0.058 Uiso 1 1 calc R . . C25 C 0.0213(3) 0.74598(12) 0.1729(4) 0.0385(8) Uani 1 1 d . . . C26 C -0.1087(3) 0.72964(13) 0.1950(4) 0.0415(9) Uani 1 1 d . . . C27 C -0.1816(4) 0.75387(15) 0.2784(5) 0.0624(12) Uani 1 1 d . . . H27 H -0.1489 0.7803 0.3281 0.075 Uiso 1 1 calc R . . C28 C -0.3040(4) 0.7391(2) 0.2887(6) 0.0821(15) Uani 1 1 d . . . H28 H -0.3537 0.7558 0.3448 0.099 Uiso 1 1 calc R . . C29 C -0.3522(4) 0.6999(2) 0.2167(6) 0.0808(15) Uani 1 1 d . . . H29 H -0.4338 0.6896 0.2255 0.097 Uiso 1 1 calc R . . C30 C -0.2817(5) 0.67648(18) 0.1338(5) 0.0756(14) Uani 1 1 d . . . H30 H -0.3156 0.6504 0.0831 0.091 Uiso 1 1 calc R . . C31 C -0.1587(4) 0.69048(14) 0.1223(4) 0.0578(11) Uani 1 1 d . . . H31 H -0.1101 0.6735 0.0657 0.069 Uiso 1 1 calc R . . N1 N 0.3582(3) 0.86696(10) 0.3645(4) 0.0524(9) Uani 1 1 d . A . N2 N 0.2301(3) 0.87872(10) 0.3253(3) 0.0443(8) Uani 1 1 d . . . N3 N 0.1939(3) 0.79500(9) 0.2556(3) 0.0392(7) Uani 1 1 d . . . N4 N 0.0835(2) 0.76999(10) 0.2766(3) 0.0389(7) Uani 1 1 d . A . H4A H 0.0563 0.7702 0.3562 0.047 Uiso 1 1 calc R . . O1 O 0.5607(3) 0.88629(11) 0.3628(4) 0.0799(10) Uani 1 1 d . A . O2 O 0.0650(2) 0.73741(9) 0.0638(3) 0.0510(7) 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 C1 0.064(7) 0.032(5) 0.065(7) -0.006(4) -0.001(4) -0.011(4) C2 0.066(5) 0.052(4) 0.109(6) 0.000(4) 0.006(5) -0.001(3) C3 0.108(6) 0.047(4) 0.117(6) -0.002(4) 0.023(5) 0.014(4) C4 0.107(6) 0.056(4) 0.139(7) 0.002(5) 0.036(6) -0.011(4) C5 0.154(7) 0.069(5) 0.114(6) 0.029(4) 0.039(5) -0.012(5) C6 0.101(5) 0.048(4) 0.091(5) 0.012(3) 0.028(4) -0.009(4) C7 0.050(3) 0.050(2) 0.066(3) 0.003(2) 0.000(2) -0.009(2) C1' 0.076(15) 0.068(16) 0.076(15) -0.001(9) 0.006(9) -0.006(9) C2' 0.099(12) 0.101(11) 0.110(12) 0.001(8) -0.009(8) 0.024(8) C3' 0.22(2) 0.22(2) 0.22(2) 0.003(10) 0.011(10) 0.004(10) C4' 0.105(10) 0.081(9) 0.105(10) 0.000(8) -0.005(8) 0.000(7) C5' 0.184(12) 0.141(11) 0.147(12) 0.015(9) 0.033(9) 0.022(9) C6' 0.140(11) 0.118(10) 0.127(11) -0.002(8) 0.019(9) 0.036(8) C8 0.042(2) 0.039(2) 0.059(3) 0.0043(18) -0.0079(19) 0.0012(17) C9 0.039(2) 0.046(2) 0.039(2) 0.0022(17) 0.0033(17) 0.0025(17) C10 0.041(2) 0.045(2) 0.043(2) 0.0039(17) 0.0032(17) 0.0016(16) C11 0.044(2) 0.045(2) 0.054(3) 0.0054(18) -0.005(2) 0.0015(17) C12 0.048(2) 0.044(2) 0.074(3) 0.003(2) -0.001(2) 0.0070(18) C13 0.055(3) 0.067(3) 0.071(3) -0.004(2) 0.018(2) 0.009(2) C14 0.061(2) 0.042(2) 0.055(3) -0.0046(18) 0.010(2) 0.0032(18) C15 0.054(3) 0.068(3) 0.124(5) -0.007(3) 0.006(3) 0.010(2) C16 0.064(3) 0.073(4) 0.151(6) -0.002(4) -0.036(4) 0.016(3) C17 0.089(4) 0.074(3) 0.116(5) -0.007(3) -0.055(4) 0.021(3) C18 0.073(3) 0.063(3) 0.067(3) 0.005(2) -0.016(3) 0.011(2) C19 0.0342(19) 0.0387(19) 0.041(2) 0.0012(17) 0.0067(17) -0.0004(15) C20 0.049(2) 0.048(2) 0.045(2) 0.0022(18) 0.0077(19) 0.0060(17) C21 0.054(2) 0.060(3) 0.053(3) 0.012(2) 0.007(2) 0.011(2) C22 0.064(3) 0.042(2) 0.082(3) 0.015(2) 0.009(3) 0.012(2) C23 0.056(3) 0.055(3) 0.078(3) -0.010(2) 0.004(2) 0.001(2) C24 0.044(2) 0.047(2) 0.053(2) 0.0018(19) 0.0023(19) 0.0014(18) C25 0.043(2) 0.042(2) 0.030(2) -0.0010(16) 0.0008(17) 0.0003(16) C26 0.0351(19) 0.051(2) 0.039(2) 0.0023(17) 0.0054(17) 0.0003(16) C27 0.046(3) 0.072(3) 0.072(3) -0.004(2) 0.016(2) -0.004(2) C28 0.038(3) 0.106(4) 0.104(4) 0.009(3) 0.017(3) 0.002(3) C29 0.040(3) 0.104(4) 0.095(4) 0.033(3) -0.003(3) -0.019(3) C30 0.067(3) 0.081(3) 0.073(3) 0.008(3) -0.014(3) -0.035(3) C31 0.059(3) 0.057(3) 0.056(3) -0.007(2) -0.001(2) -0.013(2) N1 0.0403(18) 0.0371(17) 0.078(2) 0.0053(16) 0.0005(16) -0.0013(14) N2 0.0389(18) 0.0389(16) 0.054(2) 0.0009(15) -0.0009(15) -0.0005(13) N3 0.0366(16) 0.0391(16) 0.0419(18) 0.0041(13) 0.0042(14) 0.0006(12) N4 0.0379(16) 0.0460(16) 0.0339(17) -0.0013(14) 0.0081(14) -0.0061(13) O1 0.0497(19) 0.070(2) 0.117(3) 0.0129(18) -0.0017(18) -0.0140(15) O2 0.0511(15) 0.0672(17) 0.0362(15) -0.0095(13) 0.0117(13) -0.0017(12) _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 C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.468(5) . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.218(4) . ? C7 N1 1.366(5) . ? C7 C1' 1.518(8) . ? C1' C2' 1.3900 . ? C1' C6' 1.3900 . ? C2' C3' 1.3900 . ? C2' H2' 0.9300 . ? C3' C4' 1.3900 . ? C3' H3' 0.9300 . ? C4' C5' 1.3900 . ? C4' H4' 0.9300 . ? C5' C6' 1.3900 . ? C5' H5' 0.9300 . ? C6' H6' 0.9300 . ? C8 C9 1.338(5) . ? C8 N1 1.391(4) . ? C8 H8 0.9300 . ? C9 N3 1.415(4) . ? C9 C19 1.466(5) . ? C10 N2 1.455(4) . ? C10 N3 1.491(4) . ? C10 C11 1.500(5) . ? C10 H10 0.9800 . ? C11 C18 1.384(6) . ? C11 C12 1.388(5) . ? C12 C15 1.382(6) . ? C12 C13 1.496(6) . ? C13 C14 1.515(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.469(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.383(7) . ? C15 H15 0.9300 . ? C16 C17 1.368(8) . ? C16 H16 0.9300 . ? C17 C18 1.366(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.383(5) . ? C19 C24 1.399(5) . ? C20 C21 1.374(5) . ? C20 H20 0.9300 . ? C21 C22 1.388(6) . ? C21 H21 0.9300 . ? C22 C23 1.370(6) . ? C22 H22 0.9300 . ? C23 C24 1.376(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O2 1.234(4) . ? C25 N4 1.329(4) . ? C25 C26 1.498(5) . ? C26 C27 1.366(5) . ? C26 C31 1.378(5) . ? C27 C28 1.384(6) . ? C27 H27 0.9300 . ? C28 C29 1.369(7) . ? C28 H28 0.9300 . ? C29 C30 1.336(7) . ? C29 H29 0.9300 . ? C30 C31 1.385(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? N1 N2 1.415(4) . ? N3 N4 1.404(4) . ? N4 H4A 0.8600 . ? 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 C2 C1 C6 120.0 . . ? C2 C1 C7 125.7(4) . . ? C6 C1 C7 114.0(4) . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 N1 119.1(3) . . ? O1 C7 C1 120.8(4) . . ? N1 C7 C1 120.0(4) . . ? O1 C7 C1' 123.9(6) . . ? N1 C7 C1' 116.8(6) . . ? C1 C7 C1' 5.7(9) . . ? C2' C1' C6' 120.0 . . ? C2' C1' C7 113.7(12) . . ? C6' C1' C7 126.2(12) . . ? C1' C2' C3' 120.0 . . ? C1' C2' H2' 120.0 . . ? C3' C2' H2' 120.0 . . ? C4' C3' C2' 120.0 . . ? C4' C3' H3' 120.0 . . ? C2' C3' H3' 120.0 . . ? C5' C4' C3' 120.0 . . ? C5' C4' H4' 120.0 . . ? C3' C4' H4' 120.0 . . ? C4' C5' C6' 120.0 . . ? C4' C5' H5' 120.0 . . ? C6' C5' H5' 120.0 . . ? C5' C6' C1' 120.0 . . ? C5' C6' H6' 120.0 . . ? C1' C6' H6' 120.0 . . ? C9 C8 N1 123.1(3) . . ? C9 C8 H8 118.5 . . ? N1 C8 H8 118.5 . . ? C8 C9 N3 119.2(3) . . ? C8 C9 C19 120.9(3) . . ? N3 C9 C19 119.6(3) . . ? N2 C10 N3 112.7(3) . . ? N2 C10 C11 109.7(3) . . ? N3 C10 C11 112.7(3) . . ? N2 C10 H10 107.1 . . ? N3 C10 H10 107.1 . . ? C11 C10 H10 107.1 . . ? C18 C11 C12 120.0(4) . . ? C18 C11 C10 119.6(4) . . ? C12 C11 C10 120.4(4) . . ? C15 C12 C11 119.1(4) . . ? C15 C12 C13 120.3(4) . . ? C11 C12 C13 120.5(3) . . ? C12 C13 C14 113.5(3) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N2 C14 C13 106.0(3) . . ? N2 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? N2 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C12 C15 C16 120.0(5) . . ? C12 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 120.5(5) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C11 120.3(5) . . ? C17 C18 H18 119.9 . . ? C11 C18 H18 119.9 . . ? C20 C19 C24 117.2(3) . . ? C20 C19 C9 120.0(3) . . ? C24 C19 C9 122.6(3) . . ? C21 C20 C19 122.2(4) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 119.2(4) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 119.8(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.5(4) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 121.0(4) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? O2 C25 N4 123.5(3) . . ? O2 C25 C26 120.8(3) . . ? N4 C25 C26 115.8(3) . . ? C27 C26 C31 119.1(3) . . ? C27 C26 C25 122.2(3) . . ? C31 C26 C25 118.5(3) . . ? C26 C27 C28 120.0(4) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 120.3(5) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C30 C29 C28 119.8(4) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C29 C30 C31 120.9(4) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C26 C31 C30 119.8(4) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C7 N1 C8 121.5(3) . . ? C7 N1 N2 120.6(3) . . ? C8 N1 N2 116.3(3) . . ? N1 N2 C10 109.0(3) . . ? N1 N2 C14 111.8(3) . . ? C10 N2 C14 111.5(3) . . ? N4 N3 C9 117.0(3) . . ? N4 N3 C10 116.7(2) . . ? C9 N3 C10 115.6(3) . . ? C25 N4 N3 119.7(3) . . ? C25 N4 H4A 120.2 . . ? N3 N4 H4A 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0 . . . . ? C7 C1 C2 C3 174.3(6) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? C7 C1 C6 C5 -175.0(6) . . . . ? C2 C1 C7 O1 -131.9(5) . . . . ? C6 C1 C7 O1 42.8(7) . . . . ? C2 C1 C7 N1 47.3(6) . . . . ? C6 C1 C7 N1 -138.1(4) . . . . ? C2 C1 C7 C1' 104(7) . . . . ? C6 C1 C7 C1' -82(7) . . . . ? O1 C7 C1' C2' -98.4(9) . . . . ? N1 C7 C1' C2' 86.3(9) . . . . ? C1 C7 C1' C2' -40(7) . . . . ? O1 C7 C1' C6' 84.7(12) . . . . ? N1 C7 C1' C6' -90.6(11) . . . . ? C1 C7 C1' C6' 143(8) . . . . ? C6' C1' C2' C3' 0.0 . . . . ? C7 C1' C2' C3' -177.1(11) . . . . ? C1' C2' C3' C4' 0.0 . . . . ? C2' C3' C4' C5' 0.0 . . . . ? C3' C4' C5' C6' 0.0 . . . . ? C4' C5' C6' C1' 0.0 . . . . ? C2' C1' C6' C5' 0.0 . . . . ? C7 C1' C6' C5' 176.7(12) . . . . ? N1 C8 C9 N3 9.1(6) . . . . ? N1 C8 C9 C19 -177.2(3) . . . . ? N2 C10 C11 C18 155.6(3) . . . . ? N3 C10 C11 C18 -77.9(4) . . . . ? N2 C10 C11 C12 -25.9(5) . . . . ? N3 C10 C11 C12 100.5(4) . . . . ? C18 C11 C12 C15 2.6(6) . . . . ? C10 C11 C12 C15 -175.8(4) . . . . ? C18 C11 C12 C13 -173.6(4) . . . . ? C10 C11 C12 C13 7.9(5) . . . . ? C15 C12 C13 C14 164.1(4) . . . . ? C11 C12 C13 C14 -19.7(5) . . . . ? C12 C13 C14 N2 48.0(4) . . . . ? C11 C12 C15 C16 -1.7(7) . . . . ? C13 C12 C15 C16 174.5(4) . . . . ? C12 C15 C16 C17 -0.7(8) . . . . ? C15 C16 C17 C18 2.3(8) . . . . ? C16 C17 C18 C11 -1.4(8) . . . . ? C12 C11 C18 C17 -1.1(6) . . . . ? C10 C11 C18 C17 177.4(4) . . . . ? C8 C9 C19 C20 32.8(5) . . . . ? N3 C9 C19 C20 -153.5(3) . . . . ? C8 C9 C19 C24 -142.5(4) . . . . ? N3 C9 C19 C24 31.2(5) . . . . ? C24 C19 C20 C21 1.5(5) . . . . ? C9 C19 C20 C21 -174.0(3) . . . . ? C19 C20 C21 C22 -2.2(6) . . . . ? C20 C21 C22 C23 1.0(6) . . . . ? C21 C22 C23 C24 0.7(6) . . . . ? C22 C23 C24 C19 -1.4(6) . . . . ? C20 C19 C24 C23 0.3(5) . . . . ? C9 C19 C24 C23 175.7(3) . . . . ? O2 C25 C26 C27 -150.6(4) . . . . ? N4 C25 C26 C27 29.0(5) . . . . ? O2 C25 C26 C31 25.4(5) . . . . ? N4 C25 C26 C31 -155.0(3) . . . . ? C31 C26 C27 C28 -0.1(6) . . . . ? C25 C26 C27 C28 175.9(4) . . . . ? C26 C27 C28 C29 0.6(7) . . . . ? C27 C28 C29 C30 -1.4(8) . . . . ? C28 C29 C30 C31 1.8(7) . . . . ? C27 C26 C31 C30 0.5(6) . . . . ? C25 C26 C31 C30 -175.7(4) . . . . ? C29 C30 C31 C26 -1.3(7) . . . . ? O1 C7 N1 C8 -3.3(6) . . . . ? C1 C7 N1 C8 177.5(4) . . . . ? C1' C7 N1 C8 172.2(9) . . . . ? O1 C7 N1 N2 -168.1(4) . . . . ? C1 C7 N1 N2 12.8(6) . . . . ? C1' C7 N1 N2 7.5(10) . . . . ? C9 C8 N1 C7 -150.0(4) . . . . ? C9 C8 N1 N2 15.3(5) . . . . ? C7 N1 N2 C10 118.4(4) . . . . ? C8 N1 N2 C10 -47.1(4) . . . . ? C7 N1 N2 C14 -117.9(4) . . . . ? C8 N1 N2 C14 76.7(4) . . . . ? N3 C10 N2 N1 55.8(3) . . . . ? C11 C10 N2 N1 -177.8(3) . . . . ? N3 C10 N2 C14 -68.1(3) . . . . ? C11 C10 N2 C14 58.4(4) . . . . ? C13 C14 N2 N1 167.6(3) . . . . ? C13 C14 N2 C10 -70.1(3) . . . . ? C8 C9 N3 N4 -142.5(3) . . . . ? C19 C9 N3 N4 43.7(4) . . . . ? C8 C9 N3 C10 1.1(5) . . . . ? C19 C9 N3 C10 -172.7(3) . . . . ? N2 C10 N3 N4 109.7(3) . . . . ? C11 C10 N3 N4 -15.1(4) . . . . ? N2 C10 N3 C9 -33.9(4) . . . . ? C11 C10 N3 C9 -158.8(3) . . . . ? O2 C25 N4 N3 12.5(5) . . . . ? C26 C25 N4 N3 -167.0(3) . . . . ? C9 N3 N4 C25 -124.3(3) . . . . ? C10 N3 N4 C25 92.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.318 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.096 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 0.000 0.000 -0.003 237 68 ' ' 2 0.000 0.500 0.492 237 68 ' ' _platon_squeeze_details ; N: Total Potential Solvent Accessible Void Vol .................. 479.9 Ang^3 N: Electron Count / Cell = 135 - To be included in D(calc), F000 & Mol.Wght. ; _database_code_depnum_ccdc_archive 'CCDC 940664'