# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Sebastiano Campagna' _publ_contact_author_email CAMPAGNA@UNIME.IT _publ_section_title ; Photochemically Driven Intercalation of Small Molecules into DNA by in situ irradiation ; loop_ _publ_author_name 'Sebastiano Campagna' 'M.L.Di Pietro' 'Philippe P. Laine' 'Philippe Ochsenbein' 'Fausto Puntoriero' ; F.Tuyeras ; # Attachment 'SmartIntercal.cif' data_06a _database_code_depnum_ccdc_archive 'CCDC 743209' #TrackingRef 'SmartIntercal.cif' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 'Jul 23 20:05:36 2009' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.76(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.9010(18) _cell_length_b 17.804(4) _cell_length_c 12.904(3) _cell_measurement_reflns_used 18277 _cell_measurement_temperature 123(1) _cell_measurement_theta_max 30.508 _cell_measurement_theta_min 0.998 _cell_volume 2021.1(7) _chemical_compound_source 'see text' _chemical_formula_moiety 'C28 H17 N2 1+, B F4 1-' _chemical_formula_sum 'C28 H17 B F4 N2' _chemical_formula_weight 468.25 _chemical_melting_point 'not determined' _chemical_name_common benzo(1,2)quinolizino(3,4,5,6-ija)(1,6)naphthyridin _chemical_name_systematic benzo[1,2]quinolizino[3,4,5,6-ija][1,6]naphthyridin _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_molecular_graphics SHELXP _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(1) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.952 _diffrn_measured_fraction_theta_max 0.952 _diffrn_measurement_device KappaCCD _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_orient_matrix_UB_11 0.06579 _diffrn_orient_matrix_UB_12 0.08552 _diffrn_orient_matrix_UB_13 -0.03577 _diffrn_orient_matrix_UB_21 0.04573 _diffrn_orient_matrix_UB_22 -0.02874 _diffrn_orient_matrix_UB_23 0.01541 _diffrn_orient_matrix_UB_31 0.01043 _diffrn_orient_matrix_UB_32 -0.02317 _diffrn_orient_matrix_UB_33 -0.07418 _diffrn_orient_matrix_type X=UH _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 24830 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 2.79 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 960 _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.045 _exptl_special_details 'crystal growth in acetonitrile' _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. ; _publ_section_comment ; Short intramolecular H...H contacts are due to molecular the geometry itself. ; _refine_diff_density_max 0.640 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.062 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0510 _refine_ls_abs_structure_Flack . _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.340 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 333 _refine_ls_number_reflns 5364 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.340 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1517 _refine_ls_wR_factor_ref 0.1597 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_special_details ; C-H bond distances were refined using SADI restraints (sigma = 0.03). 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. ; _reflns_number_gt 4396 _reflns_number_total 5364 _reflns_threshold_expression >2sigma(I) _symmetry_Int_Tables_number 14 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.08017(10) -0.04921(5) -0.10914(7) 0.0147(2) Uani 1 1 d . . . C2 C 0.19366(12) -0.06428(6) -0.02425(8) 0.0151(2) Uani 1 1 d . . . C3 C 0.21401(13) -0.13733(6) 0.01196(9) 0.0173(2) Uani 1 1 d D . . H3 H 0.2874(15) -0.1455(7) 0.0703(10) 0.021 Uiso 1 1 d D . . C4 C 0.12571(13) -0.19683(6) -0.03304(9) 0.0167(2) Uani 1 1 d . . . C5 C 0.01677(13) -0.18017(6) -0.11918(9) 0.0181(2) Uani 1 1 d D . . H5 H -0.0444(15) -0.2221(7) -0.1564(11) 0.022 Uiso 1 1 d D . . C6 C -0.00817(13) -0.10806(6) -0.15768(8) 0.0154(2) Uani 1 1 d . . . C7 C -0.12532(13) -0.09253(6) -0.24730(9) 0.0169(2) Uani 1 1 d . . . C8 C -0.20932(14) -0.15203(7) -0.30005(9) 0.0199(2) Uani 1 1 d D . . H8 H -0.1921(16) -0.2034(7) -0.2763(11) 0.024 Uiso 1 1 d D . . C9 C -0.31517(14) -0.13812(7) -0.38745(10) 0.0223(3) Uani 1 1 d D . . H9 H -0.3703(16) -0.1812(7) -0.4232(11) 0.027 Uiso 1 1 d D . . C10 C -0.34349(14) -0.06469(7) -0.42274(10) 0.0231(3) Uani 1 1 d D . . H10 H -0.4161(16) -0.0548(8) -0.4837(11) 0.028 Uiso 1 1 d D . . C11 C -0.26730(14) -0.00542(7) -0.36994(10) 0.0208(2) Uani 1 1 d D . . H11 H -0.2858(16) 0.0462(7) -0.3965(11) 0.025 Uiso 1 1 d D . . C12 C -0.15514(13) -0.01853(6) -0.28227(9) 0.0171(2) Uani 1 1 d . . . C13 C -0.06573(13) 0.04170(6) -0.22753(9) 0.0167(2) Uani 1 1 d . . . C14 C 0.05214(13) 0.02595(6) -0.14463(9) 0.0156(2) Uani 1 1 d . . . C15 C 0.14064(13) 0.08515(6) -0.09598(9) 0.0172(2) Uani 1 1 d . . . C16 C 0.26201(13) 0.07136(6) -0.00924(9) 0.0167(2) Uani 1 1 d . . . C17 C 0.28701(13) -0.00309(6) 0.02578(9) 0.0159(2) Uani 1 1 d . . . C18 C 0.40487(13) -0.01783(6) 0.10954(9) 0.0185(2) Uani 1 1 d D . . H18 H 0.4276(15) -0.0677(7) 0.1348(11) 0.022 Uiso 1 1 d D . . C19 C 0.49298(14) 0.03990(7) 0.15683(9) 0.0209(2) Uani 1 1 d D . . H19 H 0.5731(14) 0.0266(8) 0.2137(10) 0.025 Uiso 1 1 d D . . C20 C 0.46702(14) 0.11391(7) 0.12272(10) 0.0214(3) Uani 1 1 d D . . H20 H 0.5343(16) 0.1535(8) 0.1607(11) 0.026 Uiso 1 1 d D . . C21 C 0.35331(14) 0.12935(6) 0.04016(9) 0.0203(2) Uani 1 1 d D . . H21 H 0.3359(16) 0.1822(7) 0.0208(11) 0.024 Uiso 1 1 d D . . C22 C 0.10527(15) 0.15726(7) -0.13450(10) 0.0214(3) Uani 1 1 d D . . H22 H 0.1678(15) 0.1999(7) -0.1044(11) 0.026 Uiso 1 1 d D . . N23 N -0.00676(12) 0.17419(6) -0.21131(8) 0.0232(2) Uani 1 1 d . . . C24 C -0.09050(14) 0.11726(7) -0.25536(9) 0.0206(2) Uani 1 1 d D . . H24 H -0.1717(15) 0.1318(8) -0.3095(11) 0.025 Uiso 1 1 d D . . C25 C 0.14413(13) -0.27389(6) 0.01004(9) 0.0172(2) Uani 1 1 d . . . C26 C 0.27890(14) -0.29565(7) 0.07310(10) 0.0225(3) Uani 1 1 d D . . H26 H 0.3646(15) -0.2609(8) 0.0865(12) 0.027 Uiso 1 1 d D . . C27 C 0.29385(15) -0.36800(7) 0.11402(10) 0.0244(3) Uani 1 1 d D . . H27 H 0.3900(15) -0.3789(9) 0.1591(11) 0.029 Uiso 1 1 d D . . C28 C 0.17590(15) -0.41924(7) 0.09345(10) 0.0223(3) Uani 1 1 d D . . H28 H 0.1887(16) -0.4705(7) 0.1202(11) 0.027 Uiso 1 1 d D . . C29 C 0.04215(14) -0.39783(7) 0.03104(10) 0.0220(3) Uani 1 1 d D . . H29 H -0.0427(15) -0.4328(7) 0.0175(12) 0.026 Uiso 1 1 d D . . C30 C 0.02555(14) -0.32596(6) -0.01004(9) 0.0194(2) Uani 1 1 d D . . H30 H -0.0749(15) -0.3117(8) -0.0543(11) 0.023 Uiso 1 1 d D . . B B 0.40637(18) 0.33936(8) 0.19758(12) 0.0267(3) Uani 1 1 d . . . F1 F 0.44495(11) 0.31815(5) 0.30276(7) 0.0407(2) Uani 1 1 d . . . F2 F 0.33215(14) 0.40805(5) 0.19239(8) 0.0565(3) Uani 1 1 d . . . F3 F 0.31021(9) 0.28611(4) 0.14553(7) 0.0348(2) Uani 1 1 d . . . F4 F 0.53497(12) 0.34506(8) 0.15114(10) 0.0711(4) 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 N1 0.0176(4) 0.0098(4) 0.0158(4) 0.0002(3) 0.0003(3) 0.0008(3) C2 0.0161(5) 0.0135(5) 0.0153(5) -0.0003(4) 0.0005(4) 0.0002(4) C3 0.0189(5) 0.0130(5) 0.0186(5) 0.0014(4) -0.0015(4) -0.0002(4) C4 0.0194(5) 0.0123(5) 0.0180(5) -0.0001(4) 0.0011(4) 0.0005(4) C5 0.0222(6) 0.0108(5) 0.0199(5) -0.0008(4) -0.0018(4) -0.0004(4) C6 0.0194(5) 0.0111(5) 0.0151(5) -0.0017(4) 0.0007(4) -0.0001(4) C7 0.0199(5) 0.0152(5) 0.0145(5) -0.0003(4) -0.0008(4) 0.0005(4) C8 0.0234(6) 0.0137(5) 0.0207(6) -0.0012(4) -0.0033(5) 0.0014(4) C9 0.0224(6) 0.0194(6) 0.0227(6) -0.0027(5) -0.0040(5) 0.0001(5) C10 0.0228(6) 0.0228(6) 0.0215(6) 0.0002(5) -0.0039(5) 0.0024(5) C11 0.0226(6) 0.0170(5) 0.0217(6) 0.0027(4) -0.0003(5) 0.0031(5) C12 0.0190(5) 0.0149(5) 0.0169(5) 0.0008(4) 0.0015(4) 0.0011(4) C13 0.0193(5) 0.0143(5) 0.0162(5) 0.0009(4) 0.0019(4) 0.0006(4) C14 0.0198(5) 0.0104(5) 0.0167(5) 0.0019(4) 0.0032(4) 0.0018(4) C15 0.0202(5) 0.0128(5) 0.0187(5) 0.0008(4) 0.0032(4) 0.0003(4) C16 0.0192(5) 0.0133(5) 0.0176(5) -0.0005(4) 0.0024(4) -0.0003(4) C17 0.0181(5) 0.0130(5) 0.0165(5) -0.0008(4) 0.0017(4) -0.0012(4) C18 0.0210(5) 0.0141(5) 0.0193(5) -0.0003(4) -0.0002(4) -0.0002(4) C19 0.0223(6) 0.0185(6) 0.0205(5) -0.0023(4) -0.0012(5) -0.0012(5) C20 0.0232(6) 0.0169(5) 0.0232(6) -0.0039(4) 0.0004(5) -0.0037(5) C21 0.0249(6) 0.0126(5) 0.0225(6) -0.0009(4) 0.0008(5) -0.0017(5) C22 0.0274(6) 0.0131(5) 0.0229(6) 0.0013(4) 0.0013(5) -0.0014(5) N23 0.0312(6) 0.0135(5) 0.0239(5) 0.0029(4) 0.0008(4) -0.0011(4) C24 0.0260(6) 0.0150(5) 0.0198(5) 0.0025(4) -0.0002(5) 0.0005(5) C25 0.0217(5) 0.0121(5) 0.0168(5) 0.0009(4) -0.0005(4) 0.0016(4) C26 0.0230(6) 0.0153(5) 0.0264(6) 0.0023(5) -0.0055(5) -0.0017(5) C27 0.0260(6) 0.0189(6) 0.0257(6) 0.0045(5) -0.0036(5) 0.0021(5) C28 0.0301(6) 0.0138(5) 0.0227(6) 0.0046(4) 0.0025(5) 0.0018(5) C29 0.0248(6) 0.0149(5) 0.0260(6) 0.0013(5) 0.0027(5) -0.0022(5) C30 0.0204(5) 0.0150(5) 0.0213(5) 0.0011(4) -0.0013(4) -0.0002(4) B 0.0308(7) 0.0191(6) 0.0272(7) 0.0005(5) -0.0053(6) -0.0060(6) F1 0.0570(6) 0.0306(4) 0.0281(4) 0.0023(3) -0.0142(4) 0.0024(4) F2 0.0980(8) 0.0200(4) 0.0435(6) 0.0003(4) -0.0150(6) 0.0113(5) F3 0.0371(4) 0.0232(4) 0.0384(5) -0.0038(3) -0.0128(4) -0.0052(3) F4 0.0406(6) 0.1008(10) 0.0737(8) 0.0184(7) 0.0145(6) -0.0183(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3982(14) . ? N1 C6 1.3994(14) . ? N1 C14 1.4240(14) . ? C2 C3 1.3845(15) . ? C2 C17 1.4596(15) . ? C3 C4 1.3923(16) . ? C3 H3 0.930(12) . ? C4 C5 1.3912(16) . ? C4 C25 1.4799(15) . ? C5 C6 1.3823(15) . ? C5 H5 1.003(12) . ? C6 C7 1.4607(16) . ? C7 C12 1.4047(15) . ? C7 C8 1.4104(16) . ? C8 C9 1.3774(17) . ? C8 H8 0.970(12) . ? C9 C10 1.3947(17) . ? C9 H9 0.986(12) . ? C10 C11 1.3773(17) . ? C10 H10 0.955(12) . ? C11 C12 1.4095(16) . ? C11 H11 0.986(13) . ? C12 C13 1.4530(16) . ? C13 C24 1.4012(16) . ? C13 C14 1.4077(16) . ? C14 C15 1.4054(15) . ? C15 C22 1.3953(16) . ? C15 C16 1.4531(17) . ? C16 C21 1.4053(16) . ? C16 C17 1.4072(16) . ? C17 C18 1.4114(16) . ? C18 C19 1.3777(16) . ? C18 H18 0.957(12) . ? C19 C20 1.3973(17) . ? C19 H19 0.971(12) . ? C20 C21 1.3807(17) . ? C20 H20 1.003(13) . ? C21 H21 0.979(12) . ? C22 N23 1.3291(16) . ? C22 H22 0.986(12) . ? N23 C24 1.3330(16) . ? C24 H24 0.961(12) . ? C25 C26 1.3979(16) . ? C25 C30 1.3990(16) . ? C26 C27 1.3907(17) . ? C26 H26 0.977(12) . ? C27 C28 1.3857(18) . ? C27 H27 0.978(13) . ? C28 C29 1.3853(18) . ? C28 H28 0.976(13) . ? C29 C30 1.3844(16) . ? C29 H29 0.974(12) . ? C30 H30 1.017(12) . ? B F4 1.374(2) . ? B F3 1.3811(16) . ? B F2 1.3866(18) . ? B F1 1.4002(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 C2 N1 C6 119.78(9) . . ? C2 N1 C14 120.17(9) . . ? C6 N1 C14 120.04(9) . . ? C3 C2 N1 119.11(10) . . ? C3 C2 C17 121.02(10) . . ? N1 C2 C17 119.86(10) . . ? C2 C3 C4 122.51(10) . . ? C2 C3 H3 117.4(8) . . ? C4 C3 H3 120.0(8) . . ? C5 C4 C3 116.84(10) . . ? C5 C4 C25 121.44(10) . . ? C3 C4 C25 121.71(10) . . ? C6 C5 C4 122.65(10) . . ? C6 C5 H5 118.3(8) . . ? C4 C5 H5 119.1(8) . . ? C5 C6 N1 119.08(10) . . ? C5 C6 C7 121.10(10) . . ? N1 C6 C7 119.82(10) . . ? C12 C7 C8 119.27(10) . . ? C12 C7 C6 120.60(10) . . ? C8 C7 C6 120.13(10) . . ? C9 C8 C7 120.42(11) . . ? C9 C8 H8 118.9(9) . . ? C7 C8 H8 120.6(9) . . ? C8 C9 C10 120.19(11) . . ? C8 C9 H9 118.3(9) . . ? C10 C9 H9 121.6(9) . . ? C11 C10 C9 120.38(11) . . ? C11 C10 H10 119.1(9) . . ? C9 C10 H10 120.5(9) . . ? C10 C11 C12 120.35(11) . . ? C10 C11 H11 119.9(8) . . ? C12 C11 H11 119.6(8) . . ? C7 C12 C11 119.29(10) . . ? C7 C12 C13 118.25(10) . . ? C11 C12 C13 122.45(10) . . ? C24 C13 C14 117.13(10) . . ? C24 C13 C12 122.06(10) . . ? C14 C13 C12 120.80(10) . . ? C15 C14 C13 119.48(10) . . ? C15 C14 N1 120.15(10) . . ? C13 C14 N1 120.36(10) . . ? C22 C15 C14 116.76(11) . . ? C22 C15 C16 122.06(10) . . ? C14 C15 C16 121.18(10) . . ? C21 C16 C17 119.62(10) . . ? C21 C16 C15 122.41(10) . . ? C17 C16 C15 117.98(10) . . ? C16 C17 C18 118.93(10) . . ? C16 C17 C2 120.63(10) . . ? C18 C17 C2 120.44(10) . . ? C19 C18 C17 120.47(11) . . ? C19 C18 H18 117.7(8) . . ? C17 C18 H18 121.8(8) . . ? C18 C19 C20 120.56(11) . . ? C18 C19 H19 117.1(9) . . ? C20 C19 H19 122.4(9) . . ? C21 C20 C19 119.82(11) . . ? C21 C20 H20 123.4(8) . . ? C19 C20 H20 116.8(8) . . ? C20 C21 C16 120.60(11) . . ? C20 C21 H21 117.2(9) . . ? C16 C21 H21 122.1(9) . . ? N23 C22 C15 125.26(11) . . ? N23 C22 H22 115.7(8) . . ? C15 C22 H22 119.1(8) . . ? C22 N23 C24 116.92(10) . . ? N23 C24 C13 124.39(11) . . ? N23 C24 H24 114.5(9) . . ? C13 C24 H24 121.1(9) . . ? C26 C25 C30 118.71(10) . . ? C26 C25 C4 120.78(10) . . ? C30 C25 C4 120.50(10) . . ? C27 C26 C25 120.12(11) . . ? C27 C26 H26 119.5(8) . . ? C25 C26 H26 120.4(8) . . ? C28 C27 C26 120.74(12) . . ? C28 C27 H27 123.5(9) . . ? C26 C27 H27 115.7(9) . . ? C29 C28 C27 119.29(11) . . ? C29 C28 H28 120.4(8) . . ? C27 C28 H28 120.2(8) . . ? C30 C29 C28 120.60(11) . . ? C30 C29 H29 119.2(8) . . ? C28 C29 H29 120.2(8) . . ? C29 C30 C25 120.54(11) . . ? C29 C30 H30 118.6(8) . . ? C25 C30 H30 120.9(8) . . ? F4 B F3 109.53(13) . . ? F4 B F2 109.65(13) . . ? F3 B F2 109.06(12) . . ? F4 B F1 110.18(12) . . ? F3 B F1 109.18(11) . . ? F2 B F1 109.23(12) . . ? 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 N1 C2 C3 -1.58(15) . . . . no C6 N1 C2 C17 179.35(10) . . . . no C14 N1 C2 C3 176.98(11) . . . . no C14 N1 C2 C17 -2.08(15) . . . . no C2 N1 C6 C5 1.24(16) . . . . no C2 N1 C6 C7 -179.14(10) . . . . no C14 N1 C6 C5 -177.33(11) . . . . no C14 N1 C6 C7 2.29(16) . . . . no C2 N1 C14 C13 -177.63(11) . . . . no C2 N1 C14 C15 1.40(16) . . . . no C6 N1 C14 C13 0.94(16) . . . . no C6 N1 C14 C15 179.97(11) . . . . no C24 N23 C22 C15 -0.73(19) . . . . no C22 N23 C24 C13 -1.46(18) . . . . no N1 C2 C17 C16 1.27(16) . . . . no N1 C2 C17 C18 -178.14(11) . . . . no C3 C2 C17 C16 -177.78(11) . . . . no C3 C2 C17 C18 2.82(17) . . . . no N1 C2 C3 C4 0.10(17) . . . . no C17 C2 C3 C4 179.15(11) . . . . no C2 C3 C4 C5 1.67(17) . . . . no C2 C3 C4 C25 -176.94(11) . . . . no C3 C4 C25 C26 -21.36(18) . . . . no C3 C4 C25 C30 157.41(12) . . . . no C5 C4 C25 C26 160.09(12) . . . . no C5 C4 C25 C30 -21.14(17) . . . . no C25 C4 C5 C6 176.59(11) . . . . no C3 C4 C5 C6 -2.03(18) . . . . no C4 C5 C6 N1 0.62(17) . . . . no C4 C5 C6 C7 -179.00(11) . . . . no N1 C6 C7 C8 176.66(11) . . . . no C5 C6 C7 C12 176.60(11) . . . . no N1 C6 C7 C12 -3.01(17) . . . . no C5 C6 C7 C8 -3.73(17) . . . . no C6 C7 C8 C9 -177.08(12) . . . . no C6 C7 C12 C13 0.48(17) . . . . no C12 C7 C8 C9 2.59(18) . . . . no C6 C7 C12 C11 179.05(11) . . . . no C8 C7 C12 C13 -179.19(11) . . . . no C8 C7 C12 C11 -0.62(18) . . . . no C7 C8 C9 C10 -1.93(19) . . . . no C8 C9 C10 C11 -0.8(2) . . . . no C9 C10 C11 C12 2.73(19) . . . . no C10 C11 C12 C7 -2.02(18) . . . . no C10 C11 C12 C13 176.49(12) . . . . no C7 C12 C13 C14 2.76(17) . . . . no C11 C12 C13 C24 3.18(18) . . . . no C7 C12 C13 C24 -178.30(12) . . . . no C11 C12 C13 C14 -175.76(12) . . . . no C12 C13 C14 N1 -3.52(17) . . . . no C24 C13 C14 C15 -1.54(17) . . . . no C12 C13 C14 C15 177.44(11) . . . . no C24 C13 C14 N1 177.49(11) . . . . no C14 C13 C24 N23 2.57(18) . . . . no C12 C13 C24 N23 -176.40(12) . . . . no C13 C14 C15 C16 179.17(11) . . . . no C13 C14 C15 C22 -0.34(17) . . . . no N1 C14 C15 C22 -179.37(11) . . . . no N1 C14 C15 C16 0.13(17) . . . . no C22 C15 C16 C17 178.55(12) . . . . no C14 C15 C16 C17 -0.92(17) . . . . no C14 C15 C16 C21 179.32(12) . . . . no C16 C15 C22 N23 -177.91(12) . . . . no C22 C15 C16 C21 -1.20(19) . . . . no C14 C15 C22 N23 1.59(19) . . . . no C15 C16 C17 C2 0.23(17) . . . . no C21 C16 C17 C18 -0.60(17) . . . . no C15 C16 C17 C18 179.64(11) . . . . no C21 C16 C17 C2 180.00(11) . . . . no C17 C16 C21 C20 -0.09(19) . . . . no C15 C16 C21 C20 179.67(12) . . . . no C16 C17 C18 C19 0.62(18) . . . . no C2 C17 C18 C19 -179.97(11) . . . . no C17 C18 C19 C20 0.05(19) . . . . no C18 C19 C20 C21 -0.74(19) . . . . no C19 C20 C21 C16 0.76(19) . . . . no C4 C25 C26 C27 179.25(12) . . . . no C26 C25 C30 C29 -0.59(18) . . . . no C30 C25 C26 C27 0.46(18) . . . . no C4 C25 C30 C29 -179.39(11) . . . . no C25 C26 C27 C28 -0.3(2) . . . . no C26 C27 C28 C29 0.2(2) . . . . no C27 C28 C29 C30 -0.37(19) . . . . no C28 C29 C30 C25 0.56(19) . . . . no