# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_exp_930 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H20 N4 O2' _chemical_formula_sum 'C27 H20 N4 O2' _chemical_formula_weight 432.47 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4688(7) _cell_length_b 10.2492(6) _cell_length_c 16.9379(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.094(5) _cell_angle_gamma 90.00 _cell_volume 2148.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 '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 6969 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3780 _reflns_number_gt 2145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+0.3003P] 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 3780 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1991 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _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 -0.1297(3) 0.6005(4) -0.14028(18) 0.1266(13) Uani 1 1 d . . . O2 O -0.0601(3) 0.4156(4) -0.15660(18) 0.1212(12) Uani 1 1 d . . . N1 N -0.0879(3) 0.0999(3) 0.30846(18) 0.0777(9) Uani 1 1 d . . . N2 N -0.1707(2) 0.1441(3) 0.26036(18) 0.0771(9) Uani 1 1 d . . . N3 N -0.1419(2) 0.2595(3) 0.23363(13) 0.0562(7) Uani 1 1 d . . . N4 N -0.1059(3) 0.4909(4) -0.11744(19) 0.0828(10) Uani 1 1 d . . . C1 C 0.4033(4) 0.6453(6) 0.6596(3) 0.1027(16) Uani 1 1 d . . . H1A H 0.429(4) 0.594(5) 0.714(3) 0.16(2) Uiso 1 1 d . . . H1B H 0.459(5) 0.709(6) 0.641(3) 0.19(2) Uiso 1 1 d . . . C2 C 0.3106(3) 0.6223(4) 0.6193(2) 0.0740(10) Uani 1 1 d . . . C3 C 0.2172(3) 0.6009(4) 0.5810(2) 0.0752(11) Uani 1 1 d . . . H3 H 0.163(3) 0.656(4) 0.592(2) 0.103(14) Uiso 1 1 d . . . C4 C 0.1109(2) 0.3996(3) 0.54380(18) 0.0597(9) Uani 1 1 d . . . C5 C 0.0623(3) 0.4083(4) 0.6158(2) 0.0708(10) Uani 1 1 d . . . H5 H 0.092(3) 0.479(4) 0.652(2) 0.091(13) Uiso 1 1 d . . . C6 C -0.0115(3) 0.3218(5) 0.6343(3) 0.0810(12) Uani 1 1 d . . . H6 H -0.042(3) 0.332(4) 0.683(2) 0.086(12) Uiso 1 1 d . . . C7 C -0.0418(3) 0.2187(5) 0.5821(3) 0.0837(12) Uani 1 1 d . . . H7 H -0.098(3) 0.162(4) 0.5955(19) 0.077(11) Uiso 1 1 d . . . C8 C 0.0024(3) 0.2036(4) 0.5143(3) 0.0715(10) Uani 1 1 d . . . H8 H -0.013(2) 0.138(4) 0.4807(19) 0.067(11) Uiso 1 1 d . . . C9 C 0.0809(2) 0.2924(3) 0.49107(18) 0.0579(8) Uani 1 1 d . . . C10 C 0.2019(2) 0.3741(3) 0.40023(18) 0.0610(9) Uani 1 1 d . . . C11 C 0.2484(3) 0.3691(5) 0.3273(2) 0.0772(11) Uani 1 1 d . . . H11 H 0.227(3) 0.295(4) 0.290(2) 0.097(13) Uiso 1 1 d . . . C12 C 0.3206(4) 0.4587(6) 0.3087(3) 0.0959(14) Uani 1 1 d . . . H12 H 0.347(3) 0.444(4) 0.258(2) 0.088(12) Uiso 1 1 d . . . C13 C 0.3517(4) 0.5612(5) 0.3609(3) 0.0997(15) Uani 1 1 d . . . H13 H 0.399(4) 0.627(5) 0.345(3) 0.133(18) Uiso 1 1 d . . . C14 C 0.3099(3) 0.5725(4) 0.4304(3) 0.0840(12) Uani 1 1 d . . . H14 H 0.332(3) 0.642(4) 0.472(2) 0.101(13) Uiso 1 1 d . . . C15 C 0.2337(3) 0.4798(3) 0.45374(19) 0.0619(9) Uani 1 1 d . . . C16 C 0.1879(2) 0.4905(3) 0.52474(19) 0.0616(9) Uani 1 1 d . . . C17 C 0.1277(2) 0.2794(3) 0.42023(18) 0.0574(8) Uani 1 1 d . . . C18 C 0.0976(3) 0.1659(4) 0.3656(2) 0.0660(9) Uani 1 1 d . . . H18A H 0.156(2) 0.149(3) 0.3319(18) 0.068(10) Uiso 1 1 d . . . H18B H 0.086(2) 0.089(3) 0.3967(19) 0.075(11) Uiso 1 1 d . . . C19 C -0.0063(3) 0.1869(3) 0.31231(17) 0.0561(8) Uani 1 1 d . . . C20 C -0.0405(3) 0.2886(4) 0.26510(19) 0.0562(8) Uani 1 1 d . . . H20 H -0.008(2) 0.363(3) 0.2512(17) 0.067(10) Uiso 1 1 d . . . C21 C -0.2207(3) 0.3393(4) 0.1843(2) 0.0640(9) Uani 1 1 d . . . H21A H -0.233(2) 0.421(4) 0.216(2) 0.082(11) Uiso 1 1 d . . . H21B H -0.289(3) 0.288(3) 0.1758(19) 0.085(11) Uiso 1 1 d . . . C22 C -0.1858(2) 0.3771(3) 0.10646(18) 0.0558(8) Uani 1 1 d . . . C23 C -0.1328(3) 0.2905(4) 0.0614(2) 0.0623(9) Uani 1 1 d . . . H23 H -0.117(3) 0.212(4) 0.083(2) 0.082(12) Uiso 1 1 d . . . C24 C -0.1067(3) 0.3278(4) -0.0120(2) 0.0661(10) Uani 1 1 d . . . H24 H -0.068(2) 0.278(3) -0.0412(19) 0.071(11) Uiso 1 1 d . . . C25 C -0.1335(2) 0.4500(4) -0.03990(18) 0.0614(9) Uani 1 1 d . . . C26 C -0.1846(3) 0.5364(5) 0.0038(3) 0.0773(11) Uani 1 1 d . . . H26 H -0.198(3) 0.612(4) -0.017(2) 0.090(14) Uiso 1 1 d . . . C27 C -0.2104(3) 0.4998(4) 0.0763(2) 0.0745(11) Uani 1 1 d . . . H27 H -0.244(3) 0.558(4) 0.110(2) 0.100(13) Uiso 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 0.157(3) 0.130(3) 0.096(2) 0.049(2) 0.025(2) 0.013(3) O2 0.153(3) 0.139(3) 0.079(2) 0.009(2) 0.044(2) 0.016(2) N1 0.087(2) 0.061(2) 0.082(2) 0.0119(17) -0.0027(16) -0.0123(17) N2 0.082(2) 0.068(2) 0.079(2) 0.0103(18) -0.0005(16) -0.0190(17) N3 0.0605(16) 0.0599(18) 0.0479(14) 0.0002(14) 0.0062(12) -0.0049(14) N4 0.077(2) 0.101(3) 0.068(2) 0.015(2) -0.0014(17) -0.006(2) C1 0.086(3) 0.128(5) 0.092(3) -0.009(3) 0.008(3) -0.032(3) C2 0.083(3) 0.067(3) 0.072(2) -0.002(2) 0.009(2) -0.011(2) C3 0.078(3) 0.066(3) 0.078(2) -0.013(2) -0.001(2) 0.007(2) C4 0.0612(19) 0.060(2) 0.0558(19) 0.0057(17) -0.0005(15) 0.0135(17) C5 0.076(2) 0.074(3) 0.062(2) 0.000(2) 0.0074(19) 0.011(2) C6 0.085(3) 0.090(3) 0.069(3) 0.014(3) 0.012(2) 0.008(2) C7 0.081(3) 0.089(3) 0.083(3) 0.023(3) 0.015(2) -0.005(2) C8 0.084(3) 0.057(2) 0.072(2) 0.007(2) 0.002(2) 0.000(2) C9 0.0632(19) 0.053(2) 0.0545(19) 0.0050(17) -0.0030(15) 0.0112(17) C10 0.065(2) 0.064(2) 0.0517(19) 0.0078(17) -0.0024(15) 0.0110(18) C11 0.090(3) 0.079(3) 0.061(2) 0.006(2) 0.005(2) 0.005(2) C12 0.106(3) 0.117(4) 0.067(3) 0.012(3) 0.022(3) 0.002(3) C13 0.108(3) 0.103(4) 0.092(3) 0.012(3) 0.025(3) -0.017(3) C14 0.095(3) 0.073(3) 0.084(3) 0.005(3) 0.011(2) -0.013(2) C15 0.0640(19) 0.060(2) 0.059(2) 0.0042(18) -0.0036(16) 0.0030(17) C16 0.0628(19) 0.059(2) 0.060(2) -0.0012(18) -0.0045(16) 0.0105(18) C17 0.0628(19) 0.050(2) 0.0561(19) 0.0039(16) -0.0078(15) 0.0114(16) C18 0.081(2) 0.051(2) 0.064(2) -0.0043(19) 0.0014(19) 0.0112(19) C19 0.069(2) 0.051(2) 0.0484(17) -0.0064(16) 0.0081(15) 0.0004(17) C20 0.057(2) 0.053(2) 0.0592(19) 0.0010(18) 0.0086(15) -0.0042(17) C21 0.061(2) 0.076(3) 0.055(2) 0.005(2) 0.0065(16) 0.002(2) C22 0.0476(16) 0.064(2) 0.0529(18) 0.0004(17) -0.0039(14) -0.0026(16) C23 0.075(2) 0.058(2) 0.053(2) 0.0007(19) 0.0052(16) 0.0041(19) C24 0.069(2) 0.072(3) 0.057(2) -0.008(2) 0.0093(17) 0.001(2) C25 0.0556(19) 0.076(3) 0.0513(19) 0.0051(19) -0.0001(15) -0.0073(18) C26 0.085(3) 0.069(3) 0.080(3) 0.016(2) 0.014(2) 0.009(2) C27 0.084(3) 0.064(3) 0.080(3) 0.002(2) 0.024(2) 0.014(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 N4 1.213(4) . ? O2 N4 1.206(4) . ? N1 N2 1.314(4) . ? N1 C19 1.348(4) . ? N2 N3 1.331(4) . ? N3 C20 1.344(4) . ? N3 C21 1.459(4) . ? N4 C25 1.459(4) . ? C1 C2 1.289(5) . ? C1 H1A 1.07(6) . ? C1 H1B 1.04(6) . ? C2 C3 1.280(5) . ? C3 C16 1.495(5) . ? C3 H3 0.93(4) . ? C4 C16 1.404(5) . ? C4 C5 1.430(5) . ? C4 C9 1.436(4) . ? C5 C6 1.343(5) . ? C5 H5 0.99(4) . ? C6 C7 1.400(6) . ? C6 H6 0.96(3) . ? C7 C8 1.343(5) . ? C7 H7 0.95(3) . ? C8 C9 1.427(5) . ? C8 H8 0.89(3) . ? C9 C17 1.404(4) . ? C10 C17 1.411(4) . ? C10 C11 1.429(5) . ? C10 C15 1.436(5) . ? C11 C12 1.350(6) . ? C11 H11 1.00(4) . ? C12 C13 1.397(7) . ? C12 H12 0.97(4) . ? C13 C14 1.348(6) . ? C13 H13 0.96(5) . ? C14 C15 1.434(5) . ? C14 H14 1.02(4) . ? C15 C16 1.398(4) . ? C17 C18 1.505(5) . ? C18 C19 1.500(4) . ? C18 H18A 0.99(3) . ? C18 H18B 0.97(3) . ? C19 C20 1.351(4) . ? C20 H20 0.91(3) . ? C21 C22 1.489(4) . ? C21 H21A 1.02(4) . ? C21 H21B 1.00(3) . ? C22 C27 1.378(5) . ? C22 C23 1.390(5) . ? C23 C24 1.378(5) . ? C23 H23 0.90(4) . ? C24 C25 1.366(5) . ? C24 H24 0.89(3) . ? C25 C26 1.362(5) . ? C26 C27 1.360(5) . ? C26 H26 0.86(4) . ? C27 H27 0.95(4) . ? 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 N2 N1 C19 109.4(3) . . ? N1 N2 N3 107.0(3) . . ? N2 N3 C20 110.0(3) . . ? N2 N3 C21 120.2(3) . . ? C20 N3 C21 129.5(3) . . ? O2 N4 O1 122.1(4) . . ? O2 N4 C25 119.4(4) . . ? O1 N4 C25 118.5(4) . . ? C2 C1 H1A 121(3) . . ? C2 C1 H1B 123(3) . . ? H1A C1 H1B 116(4) . . ? C3 C2 C1 178.3(4) . . ? C2 C3 C16 126.0(4) . . ? C2 C3 H3 116(3) . . ? C16 C3 H3 118(3) . . ? C16 C4 C5 121.9(3) . . ? C16 C4 C9 119.9(3) . . ? C5 C4 C9 118.2(3) . . ? C6 C5 C4 122.2(4) . . ? C6 C5 H5 124(2) . . ? C4 C5 H5 114(2) . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 119(2) . . ? C7 C6 H6 121(2) . . ? C8 C7 C6 121.3(4) . . ? C8 C7 H7 122(2) . . ? C6 C7 H7 117(2) . . ? C7 C8 C9 122.0(4) . . ? C7 C8 H8 124(2) . . ? C9 C8 H8 114(2) . . ? C17 C9 C8 123.1(3) . . ? C17 C9 C4 120.0(3) . . ? C8 C9 C4 116.8(3) . . ? C17 C10 C11 122.1(4) . . ? C17 C10 C15 120.4(3) . . ? C11 C10 C15 117.6(3) . . ? C12 C11 C10 122.0(4) . . ? C12 C11 H11 120(2) . . ? C10 C11 H11 117(2) . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 114(2) . . ? C13 C12 H12 125(2) . . ? C14 C13 C12 120.7(5) . . ? C14 C13 H13 120(3) . . ? C12 C13 H13 119(3) . . ? C13 C14 C15 121.6(5) . . ? C13 C14 H14 125(2) . . ? C15 C14 H14 114(2) . . ? C16 C15 C14 122.7(4) . . ? C16 C15 C10 119.5(3) . . ? C14 C15 C10 117.8(3) . . ? C15 C16 C4 120.6(3) . . ? C15 C16 C3 121.0(3) . . ? C4 C16 C3 118.4(3) . . ? C9 C17 C10 119.6(3) . . ? C9 C17 C18 120.0(3) . . ? C10 C17 C18 120.4(3) . . ? C19 C18 C17 112.9(3) . . ? C19 C18 H18A 108.6(17) . . ? C17 C18 H18A 110.1(19) . . ? C19 C18 H18B 105(2) . . ? C17 C18 H18B 109.9(19) . . ? H18A C18 H18B 110(3) . . ? N1 C19 C20 107.5(3) . . ? N1 C19 C18 121.6(3) . . ? C20 C19 C18 130.8(3) . . ? N3 C20 C19 106.0(3) . . ? N3 C20 H20 120.6(19) . . ? C19 C20 H20 133.3(19) . . ? N3 C21 C22 113.8(3) . . ? N3 C21 H21A 107.3(19) . . ? C22 C21 H21A 109.5(19) . . ? N3 C21 H21B 107(2) . . ? C22 C21 H21B 110.4(19) . . ? H21A C21 H21B 109(3) . . ? C27 C22 C23 118.6(3) . . ? C27 C22 C21 119.3(3) . . ? C23 C22 C21 122.0(3) . . ? C24 C23 C22 120.0(4) . . ? C24 C23 H23 124(2) . . ? C22 C23 H23 116(2) . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 117(2) . . ? C23 C24 H24 123(2) . . ? C26 C25 C24 121.3(3) . . ? C26 C25 N4 118.7(4) . . ? C24 C25 N4 120.0(4) . . ? C27 C26 C25 119.4(4) . . ? C27 C26 H26 124(3) . . ? C25 C26 H26 116(3) . . ? C26 C27 C22 121.3(4) . . ? C26 C27 H27 122(2) . . ? C22 C27 H27 116(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.139 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 942856' ####################################################################### # # 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_pr _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H26 N8 O5, 0.52(H2 O)' _chemical_formula_sum 'C34 H27.05 N8 O5.53 ' _chemical_formula_weight 636.09 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 P21/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 17.5453(9) _cell_length_b 9.9306(6) _cell_length_c 18.5780(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.562(2) _cell_angle_gamma 90.00 _cell_volume 3068.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1295 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 '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 27430 _diffrn_reflns_av_R_equivalents 0.1385 _diffrn_reflns_av_sigmaI/netI 0.0763 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.25 _reflns_number_total 5375 _reflns_number_gt 2745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^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 5375 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 0.65125(10) 0.83124(17) 0.55426(9) 0.0913(6) Uani 1 1 d . . . O2 O 0.42742(14) 0.5019(3) 0.73818(16) 0.1631(12) Uani 1 1 d . . . O3 O 0.43352(13) 0.6631(3) 0.66437(15) 0.1424(9) Uani 1 1 d . . . O4 O 0.48686(17) 1.1035(4) 0.58963(17) 0.1606(12) Uani 1 1 d . . . O5 O 0.46837(17) 1.3095(4) 0.61490(18) 0.2007(17) Uani 1 1 d . . . O6 O 0.0032(4) 0.5449(8) 0.4284(4) 0.194(3) Uani 0.525(5) 1 d PG . . H6A H -0.0378 0.5048 0.4329 0.290 Uiso 0.525(5) 1 d PG . . H6B H 0.0272 0.5865 0.4694 0.290 Uiso 0.525(5) 1 d PG . . N1 N 0.90085(12) 0.5575(2) 0.65487(11) 0.0726(5) Uani 1 1 d . . . N2 N 0.86040(12) 0.47789(18) 0.68656(12) 0.0735(5) Uani 1 1 d . . . N3 N 0.84653(10) 0.54828(18) 0.74249(10) 0.0596(5) Uani 1 1 d . . . N4 N 0.46500(17) 0.5773(3) 0.71054(17) 0.1057(8) Uani 1 1 d . . . N5 N 0.89105(12) 1.12285(19) 0.47275(11) 0.0700(5) Uani 1 1 d . . . N6 N 0.84036(13) 1.2216(2) 0.44233(11) 0.0713(5) Uani 1 1 d . . . N7 N 0.82083(12) 1.28014(17) 0.49856(11) 0.0674(5) Uani 1 1 d . . . N8 N 0.5018(2) 1.2246(5) 0.5909(2) 0.1333(12) Uani 1 1 d . . . C1 C 0.85229(13) 0.82976(18) 0.54259(11) 0.0499(5) Uani 1 1 d . . . C2 C 0.89310(18) 0.7738(2) 0.49620(14) 0.0670(6) Uani 1 1 d . . . H2 H 0.9571(15) 0.771(2) 0.5131(13) 0.089(8) Uiso 1 1 d . . . C3 C 0.8519(2) 0.7118(2) 0.42845(16) 0.0775(8) Uani 1 1 d . . . H3 H 0.8878(13) 0.669(2) 0.4038(12) 0.077(7) Uiso 1 1 d . . . C4 C 0.7700(2) 0.7066(3) 0.40444(17) 0.0829(9) Uani 1 1 d . . . H4 H 0.7451(13) 0.666(2) 0.3598(14) 0.082(8) Uiso 1 1 d . . . C5 C 0.7282(2) 0.7583(2) 0.44850(14) 0.0696(7) Uani 1 1 d . . . H5 H 0.6760(13) 0.758(2) 0.4389(12) 0.060(8) Uiso 1 1 d . . . C6 C 0.76836(13) 0.81802(19) 0.51908(12) 0.0529(5) Uani 1 1 d . . . C7 C 0.76431(12) 0.93861(18) 0.63811(11) 0.0476(5) Uani 1 1 d . . . C8 C 0.72000(17) 0.9921(2) 0.68172(15) 0.0651(7) Uani 1 1 d . . . H8 H 0.6704(11) 0.9786(18) 0.6674(10) 0.049(7) Uiso 1 1 d . . . C9 C 0.75614(18) 1.0612(2) 0.74694(16) 0.0699(7) Uani 1 1 d . . . H9 H 0.7270(12) 1.0961(19) 0.7751(11) 0.066(7) Uiso 1 1 d . . . C10 C 0.83804(17) 1.0777(2) 0.77110(14) 0.0664(6) Uani 1 1 d . . . H10 H 0.8671(12) 1.122(2) 0.8208(12) 0.079(7) Uiso 1 1 d . . . C11 C 0.88253(16) 1.0256(2) 0.72873(13) 0.0601(6) Uani 1 1 d . . . H11 H 0.9391(11) 1.0377(17) 0.7472(9) 0.049(6) Uiso 1 1 d . . . C12 C 0.84760(11) 0.95616(18) 0.66103(11) 0.0468(5) Uani 1 1 d . . . C13 C 0.90005(11) 0.89732(18) 0.61698(10) 0.0483(5) Uani 1 1 d . . . C14 C 0.72274(13) 0.8615(2) 0.56853(12) 0.0574(6) Uani 1 1 d . . . C15 C 0.95729(14) 0.7909(2) 0.66837(14) 0.0588(6) Uani 1 1 d . . . H15A H 0.9932(11) 0.7550(16) 0.6410(10) 0.050(5) Uiso 1 1 d . . . H15B H 0.9907(12) 0.8393(19) 0.7135(12) 0.067(6) Uiso 1 1 d . . . C16 C 0.91333(12) 0.6782(2) 0.69097(12) 0.0525(5) Uani 1 1 d . . . C17 C 0.87902(14) 0.6715(2) 0.74653(14) 0.0618(6) Uani 1 1 d . . . H17 H 0.8764(13) 0.731(2) 0.7834(13) 0.079(8) Uiso 1 1 d . . . C18 C 0.80411(16) 0.4861(3) 0.79013(17) 0.0732(7) Uani 1 1 d . . . H18A H 0.8361(17) 0.517(3) 0.8462(18) 0.135(11) Uiso 1 1 d . . . H18B H 0.8176(14) 0.392(2) 0.7863(12) 0.094(8) Uiso 1 1 d . . . C19 C 0.71544(14) 0.5158(2) 0.76681(12) 0.0621(6) Uani 1 1 d . . . C20 C 0.66893(19) 0.4348(3) 0.79630(16) 0.0851(8) Uani 1 1 d . . . H20 H 0.6994(16) 0.357(3) 0.8315(16) 0.126(10) Uiso 1 1 d . . . C21 C 0.5876(2) 0.4567(3) 0.77929(18) 0.0958(9) Uani 1 1 d . . . H21 H 0.5534(17) 0.390(3) 0.8011(16) 0.142(11) Uiso 1 1 d . . . C22 C 0.55321(16) 0.5604(3) 0.73212(15) 0.0781(7) Uani 1 1 d . . . C23 C 0.59694(19) 0.6435(3) 0.70254(17) 0.0837(8) Uani 1 1 d . . . H23 H 0.5776(15) 0.714(2) 0.6709(14) 0.090(9) Uiso 1 1 d . . . C24 C 0.67905(17) 0.6222(2) 0.72006(14) 0.0725(7) Uani 1 1 d . . . H24 H 0.7122(13) 0.687(2) 0.6991(12) 0.087(7) Uiso 1 1 d . . . C25 C 0.95192(14) 1.0125(2) 0.59853(15) 0.0587(6) Uani 1 1 d . . . H25A H 0.9839(12) 1.0523(18) 0.6452(12) 0.065(6) Uiso 1 1 d . . . H25B H 0.9888(10) 0.9733(17) 0.5761(9) 0.046(5) Uiso 1 1 d . . . C26 C 0.90253(12) 1.1186(2) 0.54874(12) 0.0526(5) Uani 1 1 d . . . C27 C 0.85860(16) 1.2191(2) 0.56556(15) 0.0692(7) Uani 1 1 d . . . H27 H 0.8561(13) 1.260(2) 0.6189(14) 0.094(7) Uiso 1 1 d . . . C28 C 0.7592(2) 1.3856(3) 0.48301(19) 0.0829(8) Uani 1 1 d . . . H28A H 0.7417(13) 1.397(2) 0.4258(15) 0.093(8) Uiso 1 1 d . . . H28B H 0.7871(13) 1.466(2) 0.5136(13) 0.094(8) Uiso 1 1 d . . . C29 C 0.68868(16) 1.3426(2) 0.50722(13) 0.0730(7) Uani 1 1 d . . . C30 C 0.6609(2) 1.2120(3) 0.49853(16) 0.0895(9) Uani 1 1 d . . . H30 H 0.6930(16) 1.146(3) 0.4815(15) 0.119(10) Uiso 1 1 d . . . C31 C 0.5982(2) 1.1723(4) 0.52341(18) 0.0936(9) Uani 1 1 d . . . H31 H 0.5764(17) 1.088(3) 0.5192(16) 0.118(12) Uiso 1 1 d . . . C32 C 0.56385(19) 1.2659(4) 0.55685(15) 0.0919(9) Uani 1 1 d . . . C33 C 0.5878(2) 1.3971(5) 0.5628(2) 0.1236(13) Uani 1 1 d . . . H33 H 0.5617(18) 1.456(3) 0.5849(18) 0.144(13) Uiso 1 1 d . . . C34 C 0.6506(2) 1.4357(3) 0.53858(17) 0.0995(9) Uani 1 1 d . . . H34 H 0.6747(17) 1.529(3) 0.5427(16) 0.133(11) Uiso 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 0.0539(11) 0.1187(14) 0.0941(13) -0.0165(10) 0.0135(9) -0.0187(10) O2 0.0900(18) 0.246(3) 0.172(2) 0.017(2) 0.0686(17) 0.0056(19) O3 0.0901(17) 0.161(2) 0.149(2) -0.0062(17) -0.0004(15) 0.0317(15) O4 0.113(2) 0.239(3) 0.130(2) 0.036(3) 0.0382(16) -0.009(2) O5 0.102(2) 0.313(4) 0.205(3) -0.157(3) 0.073(2) -0.066(2) O6 0.149(5) 0.227(7) 0.225(6) -0.070(5) 0.088(5) 0.008(4) N1 0.0838(14) 0.0688(13) 0.0697(13) -0.0036(11) 0.0306(11) 0.0053(11) N2 0.0885(15) 0.0625(12) 0.0744(14) -0.0052(11) 0.0327(12) 0.0037(11) N3 0.0621(12) 0.0575(12) 0.0588(13) 0.0084(10) 0.0186(10) 0.0081(10) N4 0.078(2) 0.141(3) 0.096(2) -0.0230(18) 0.0259(17) 0.0084(19) N5 0.0805(14) 0.0778(13) 0.0605(14) -0.0010(11) 0.0350(11) 0.0041(12) N6 0.0901(15) 0.0738(13) 0.0594(13) 0.0010(11) 0.0370(11) 0.0027(12) N7 0.0941(15) 0.0529(11) 0.0646(14) -0.0004(10) 0.0385(12) 0.0024(11) N8 0.073(2) 0.206(4) 0.105(2) -0.047(3) 0.0064(18) -0.017(3) C1 0.0575(15) 0.0467(11) 0.0481(13) 0.0018(10) 0.0207(11) -0.0002(10) C2 0.080(2) 0.0678(15) 0.0594(17) -0.0030(13) 0.0309(14) 0.0022(14) C3 0.111(3) 0.0679(16) 0.0619(19) -0.0016(14) 0.0391(19) 0.0081(17) C4 0.131(3) 0.0603(16) 0.0492(19) -0.0066(14) 0.017(2) -0.0089(18) C5 0.075(2) 0.0640(16) 0.0573(18) -0.0014(13) 0.0037(16) -0.0091(14) C6 0.0568(15) 0.0468(12) 0.0511(14) -0.0001(10) 0.0115(12) -0.0030(10) C7 0.0443(13) 0.0474(11) 0.0517(13) 0.0056(10) 0.0162(10) 0.0001(10) C8 0.0501(17) 0.0717(16) 0.0783(19) 0.0070(14) 0.0274(15) 0.0056(13) C9 0.080(2) 0.0715(16) 0.0700(19) -0.0036(14) 0.0414(17) 0.0070(15) C10 0.081(2) 0.0670(14) 0.0575(17) -0.0117(13) 0.0302(15) -0.0090(14) C11 0.0511(15) 0.0692(15) 0.0585(15) -0.0071(12) 0.0153(13) -0.0103(12) C12 0.0454(13) 0.0469(11) 0.0491(13) 0.0023(10) 0.0161(10) -0.0009(10) C13 0.0425(12) 0.0535(12) 0.0499(13) -0.0004(10) 0.0160(10) -0.0020(10) C14 0.0414(14) 0.0591(13) 0.0640(15) 0.0051(11) 0.0060(12) -0.0026(11) C15 0.0451(14) 0.0711(16) 0.0595(16) 0.0021(13) 0.0156(13) 0.0085(12) C16 0.0479(13) 0.0587(14) 0.0466(14) 0.0014(11) 0.0090(10) 0.0123(11) C17 0.0733(17) 0.0577(15) 0.0537(16) -0.0016(13) 0.0194(13) 0.0054(13) C18 0.0712(19) 0.0705(18) 0.081(2) 0.0221(15) 0.0288(15) 0.0079(14) C19 0.0696(17) 0.0576(13) 0.0596(15) 0.0039(12) 0.0213(12) -0.0005(13) C20 0.079(2) 0.0883(19) 0.097(2) 0.0247(16) 0.0409(17) 0.0092(17) C21 0.088(2) 0.105(2) 0.104(2) 0.0151(19) 0.0438(19) -0.002(2) C22 0.0643(19) 0.092(2) 0.0800(19) -0.0114(16) 0.0257(15) 0.0071(16) C23 0.082(2) 0.0764(19) 0.085(2) 0.0075(16) 0.0161(17) 0.0109(17) C24 0.0676(19) 0.0690(16) 0.0776(18) 0.0092(14) 0.0185(14) 0.0005(14) C25 0.0492(15) 0.0679(15) 0.0630(17) -0.0081(13) 0.0236(13) -0.0065(13) C26 0.0578(14) 0.0520(13) 0.0539(15) -0.0062(11) 0.0260(11) -0.0127(11) C27 0.100(2) 0.0556(14) 0.0552(17) 0.0004(13) 0.0297(15) 0.0023(13) C28 0.119(3) 0.0602(17) 0.078(2) 0.0096(16) 0.0438(19) 0.0133(18) C29 0.093(2) 0.0645(17) 0.0602(16) 0.0073(13) 0.0230(14) 0.0170(15) C30 0.118(3) 0.0680(19) 0.095(2) 0.0088(16) 0.0510(19) 0.0147(19) C31 0.097(3) 0.090(2) 0.091(2) 0.0155(19) 0.0268(19) 0.009(2) C32 0.064(2) 0.139(3) 0.0679(19) -0.0139(19) 0.0140(15) -0.001(2) C33 0.081(2) 0.153(4) 0.138(3) -0.070(3) 0.036(2) -0.003(3) C34 0.093(2) 0.089(2) 0.116(2) -0.0322(18) 0.0313(19) 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 C14 1.234(2) . ? O2 N4 1.214(3) . ? O3 N4 1.211(3) . ? O4 N8 1.229(4) . ? O5 N8 1.192(4) . ? N1 N2 1.319(2) . ? N1 C16 1.357(2) . ? N2 N3 1.337(2) . ? N3 C17 1.342(3) . ? N3 C18 1.462(3) . ? N4 C22 1.479(3) . ? N5 N6 1.323(2) . ? N5 C26 1.362(2) . ? N6 N7 1.332(2) . ? N7 C27 1.353(3) . ? N7 C28 1.467(3) . ? N8 C32 1.481(5) . ? C1 C2 1.399(3) . ? C1 C6 1.401(3) . ? C1 C13 1.525(3) . ? C2 C3 1.381(3) . ? C3 C4 1.363(4) . ? C4 C5 1.362(4) . ? C5 C6 1.407(3) . ? C6 C14 1.463(3) . ? C7 C8 1.394(3) . ? C7 C12 1.397(2) . ? C7 C14 1.480(3) . ? C8 C9 1.361(3) . ? C9 C10 1.372(3) . ? C10 C11 1.374(3) . ? C11 C12 1.393(3) . ? C12 C13 1.529(3) . ? C13 C15 1.558(3) . ? C13 C25 1.566(3) . ? C15 C16 1.493(3) . ? C16 C17 1.352(3) . ? C18 C19 1.505(3) . ? C19 C20 1.378(3) . ? C19 C24 1.388(3) . ? C20 C21 1.377(4) . ? C21 C22 1.363(4) . ? C22 C23 1.357(4) . ? C23 C24 1.388(3) . ? C25 C26 1.486(3) . ? C26 C27 1.357(3) . ? C28 C29 1.506(3) . ? C29 C34 1.375(3) . ? C29 C30 1.377(3) . ? C30 C31 1.380(4) . ? C31 C32 1.360(4) . ? C32 C33 1.362(4) . ? C33 C34 1.372(4) . ? 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 N2 N1 C16 109.50(18) . . ? N1 N2 N3 106.88(17) . . ? N2 N3 C17 109.93(19) . . ? N2 N3 C18 120.2(2) . . ? C17 N3 C18 129.8(2) . . ? O3 N4 O2 123.2(3) . . ? O3 N4 C22 118.3(3) . . ? O2 N4 C22 118.5(3) . . ? N6 N5 C26 108.85(18) . . ? N5 N6 N7 107.11(18) . . ? N6 N7 C27 110.67(19) . . ? N6 N7 C28 121.0(2) . . ? C27 N7 C28 128.0(2) . . ? O5 N8 O4 124.9(5) . . ? O5 N8 C32 118.7(4) . . ? O4 N8 C32 116.4(4) . . ? C2 C1 C6 117.9(2) . . ? C2 C1 C13 119.5(2) . . ? C6 C1 C13 122.61(18) . . ? C3 C2 C1 121.1(3) . . ? C4 C3 C2 120.4(3) . . ? C5 C4 C3 120.1(3) . . ? C4 C5 C6 120.9(3) . . ? C1 C6 C5 119.4(2) . . ? C1 C6 C14 120.70(19) . . ? C5 C6 C14 119.9(2) . . ? C8 C7 C12 119.9(2) . . ? C8 C7 C14 119.6(2) . . ? C12 C7 C14 120.52(19) . . ? C9 C8 C7 121.4(3) . . ? C8 C9 C10 119.6(3) . . ? C9 C10 C11 119.6(3) . . ? C10 C11 C12 122.5(2) . . ? C11 C12 C7 116.98(19) . . ? C11 C12 C13 120.36(19) . . ? C7 C12 C13 122.60(17) . . ? C1 C13 C12 113.74(16) . . ? C1 C13 C15 108.54(16) . . ? C12 C13 C15 108.17(16) . . ? C1 C13 C25 108.23(16) . . ? C12 C13 C25 109.20(16) . . ? C15 C13 C25 108.87(16) . . ? O1 C14 C6 121.0(2) . . ? O1 C14 C7 119.9(2) . . ? C6 C14 C7 119.04(19) . . ? C16 C15 C13 113.01(17) . . ? C17 C16 N1 107.0(2) . . ? C17 C16 C15 130.3(2) . . ? N1 C16 C15 122.7(2) . . ? N3 C17 C16 106.6(2) . . ? N3 C18 C19 114.9(2) . . ? C20 C19 C24 118.7(2) . . ? C20 C19 C18 117.4(2) . . ? C24 C19 C18 123.8(2) . . ? C21 C20 C19 121.2(3) . . ? C22 C21 C20 118.8(3) . . ? C23 C22 C21 121.9(3) . . ? C23 C22 N4 120.0(3) . . ? C21 C22 N4 118.1(3) . . ? C22 C23 C24 119.4(3) . . ? C19 C24 C23 119.9(3) . . ? C26 C25 C13 112.96(17) . . ? C27 C26 N5 108.0(2) . . ? C27 C26 C25 129.8(2) . . ? N5 C26 C25 122.1(2) . . ? N7 C27 C26 105.4(2) . . ? N7 C28 C29 111.3(2) . . ? C34 C29 C30 118.8(3) . . ? C34 C29 C28 119.5(3) . . ? C30 C29 C28 121.7(3) . . ? C29 C30 C31 121.4(3) . . ? C32 C31 C30 118.3(3) . . ? C31 C32 C33 121.4(4) . . ? C31 C32 N8 119.9(4) . . ? C33 C32 N8 118.7(4) . . ? C32 C33 C34 120.0(4) . . ? C33 C34 C29 120.0(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.156 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 921613'