Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2003 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Beddard, Godfrey' 'Reid, Gavin' Roth,Wolfgang 'W Whitaker, B' 'Whittaker, Douglas J.' 'Williamson, Mathew J. I.' _publ_contact_author_name 'Prof Godfrey Beddard' _publ_contact_author_address ; Dept of Chemistry University of Leeds Woodhouse Lane Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email GODFREY.BEDDARD@CHEM.LEEDS.AC.UK _publ_requested_journal 'Photochemical & Photobiological Sciences' _publ_section_title ; Excited State Dynamics and Rapid Internal Conversion in a Stable Dipole Molecule ; data_ron104 _database_code_CSD 207597 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C28 H19 N O2' _chemical_formula_sum 'C28 H19 N O2' _chemical_formula_weight 401.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.1602(2) _cell_length_b 8.3306(2) _cell_length_c 21.5276(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.0049(14) _cell_angle_gamma 90.00 _cell_volume 1971.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 47521 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9636 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 190(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area-detector scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18459 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 30.46 _reflns_number_total 5395 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KCD (Nonius, 1997)' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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 w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.3982P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5395 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.40403(8) 0.58674(11) 0.05736(4) 0.0339(2) Uani 1 d . . . C2 C 0.29900(9) 0.50861(12) 0.02747(5) 0.0339(2) Uani 1 d . . . C3 C 0.24448(10) 0.53812(13) -0.03715(5) 0.0354(2) Uani 1 d . . . O3 O 0.27769(8) 0.63017(11) -0.07590(4) 0.0473(2) Uani 1 d . . . C4 C 0.13533(10) 0.43221(13) -0.05066(5) 0.0365(2) Uani 1 d . . . C5 C 0.05291(11) 0.41345(15) -0.10581(6) 0.0443(3) Uani 1 d . . . H5 H 0.0608 0.4723 -0.1427 0.053 Uiso 1 calc R . . C6 C -0.04234(11) 0.30544(16) -0.10576(6) 0.0486(3) Uani 1 d . . . H6 H -0.1006 0.2904 -0.1431 0.058 Uiso 1 calc R . . C7 C -0.05288(12) 0.21978(16) -0.05186(6) 0.0489(3) Uani 1 d . . . H7 H -0.1183 0.1464 -0.0527 0.059 Uiso 1 calc R . . C8 C 0.03107(11) 0.23938(15) 0.00374(6) 0.0453(3) Uani 1 d . . . H8 H 0.0238 0.1805 0.0407 0.054 Uiso 1 calc R . . C9 C 0.12485(10) 0.34695(13) 0.00334(5) 0.0372(2) Uani 1 d . . . C10 C 0.22830(10) 0.39086(14) 0.05484(5) 0.0380(2) Uani 1 d . . . O10 O 0.24265(9) 0.33206(12) 0.10810(4) 0.0551(3) Uani 1 d . . . C11 C 0.46467(10) 0.52953(13) 0.12084(5) 0.0367(2) Uani 1 d . . . H11A H 0.5281 0.4500 0.1156 0.044 Uiso 1 calc R . . H11B H 0.4038 0.4752 0.1420 0.044 Uiso 1 calc R . . C12 C 0.52285(9) 0.66683(13) 0.16247(5) 0.0349(2) Uani 1 d . . . H12 H 0.5785 0.6168 0.1987 0.042 Uiso 1 calc R . . C13 C 0.60106(9) 0.76836(13) 0.12740(5) 0.0349(2) Uani 1 d . . . C14 C 0.70382(10) 0.85492(13) 0.15882(5) 0.0377(2) Uani 1 d . . . C15 C 0.74327(11) 0.84742(14) 0.22509(6) 0.0431(3) Uani 1 d . . . H15 H 0.6992 0.7842 0.2501 0.052 Uiso 1 calc R . . C16 C 0.84416(11) 0.93026(16) 0.25341(6) 0.0504(3) Uani 1 d . . . H16 H 0.8702 0.9225 0.2977 0.060 Uiso 1 calc R . . C17 C 0.90940(11) 1.02662(17) 0.21734(7) 0.0532(3) Uani 1 d . . . H17 H 0.9792 1.0837 0.2374 0.064 Uiso 1 calc R . . C18 C 0.87326(11) 1.03879(16) 0.15372(7) 0.0487(3) Uani 1 d . . . H18 H 0.9178 1.1051 0.1299 0.058 Uiso 1 calc R . . C19 C 0.76997(10) 0.95381(14) 0.12250(6) 0.0404(3) Uani 1 d . . . C20 C 0.73014(11) 0.96617(14) 0.05635(6) 0.0431(3) Uani 1 d . . . H20 H 0.7733 1.0333 0.0322 0.052 Uiso 1 calc R . . C21 C 0.63137(11) 0.88357(14) 0.02717(5) 0.0411(3) Uani 1 d . . . H21 H 0.6058 0.8936 -0.0171 0.049 Uiso 1 calc R . . C22 C 0.56599(10) 0.78206(13) 0.06262(5) 0.0361(2) Uani 1 d . . . C23 C 0.45844(10) 0.70133(13) 0.03076(5) 0.0367(2) Uani 1 d . . . H23 H 0.4255 0.7322 -0.0112 0.044 Uiso 1 calc R . . C24 C 0.42946(9) 0.76383(13) 0.19030(5) 0.0344(2) Uani 1 d . . . C25 C 0.36520(10) 0.89115(14) 0.15846(5) 0.0395(2) Uani 1 d . . . H25 H 0.3826 0.9238 0.1187 0.047 Uiso 1 calc R . . C26 C 0.27613(11) 0.97092(15) 0.18410(6) 0.0474(3) Uani 1 d . . . H26 H 0.2322 1.0570 0.1619 0.057 Uiso 1 calc R . . C27 C 0.25174(11) 0.92409(17) 0.24236(6) 0.0510(3) Uani 1 d . . . H27 H 0.1902 0.9776 0.2599 0.061 Uiso 1 calc R . . C28 C 0.31610(12) 0.80034(17) 0.27504(6) 0.0503(3) Uani 1 d . . . H28 H 0.2999 0.7699 0.3153 0.060 Uiso 1 calc R . . C29 C 0.40433(11) 0.72054(14) 0.24909(5) 0.0427(3) Uani 1 d . . . H29 H 0.4483 0.6351 0.2717 0.051 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0373(4) 0.0339(4) 0.0304(4) -0.0005(3) 0.0057(3) 0.0039(3) C2 0.0362(5) 0.0344(5) 0.0311(5) -0.0006(4) 0.0057(4) 0.0032(4) C3 0.0402(5) 0.0351(5) 0.0311(5) 0.0005(4) 0.0068(4) 0.0041(4) O3 0.0551(5) 0.0516(5) 0.0336(4) 0.0076(4) 0.0033(3) -0.0077(4) C4 0.0380(5) 0.0361(5) 0.0354(5) -0.0015(4) 0.0066(4) 0.0050(4) C5 0.0455(6) 0.0478(6) 0.0377(6) 0.0002(5) 0.0019(5) 0.0004(5) C6 0.0433(6) 0.0531(7) 0.0465(6) -0.0049(6) 0.0000(5) -0.0014(5) C7 0.0412(6) 0.0506(7) 0.0549(7) -0.0045(6) 0.0082(5) -0.0056(5) C8 0.0436(6) 0.0486(6) 0.0447(6) 0.0025(5) 0.0102(5) -0.0025(5) C9 0.0375(5) 0.0378(5) 0.0370(5) -0.0008(4) 0.0082(4) 0.0038(4) C10 0.0405(6) 0.0405(6) 0.0334(5) 0.0018(4) 0.0073(4) 0.0019(4) O10 0.0590(5) 0.0661(6) 0.0382(4) 0.0146(4) 0.0025(4) -0.0140(5) C11 0.0407(5) 0.0347(5) 0.0330(5) 0.0033(4) 0.0016(4) 0.0050(4) C12 0.0351(5) 0.0367(5) 0.0314(5) 0.0030(4) 0.0019(4) 0.0035(4) C13 0.0331(5) 0.0346(5) 0.0374(5) 0.0007(4) 0.0069(4) 0.0053(4) C14 0.0330(5) 0.0362(5) 0.0436(6) -0.0008(4) 0.0060(4) 0.0058(4) C15 0.0397(6) 0.0429(6) 0.0446(6) 0.0009(5) 0.0016(5) 0.0028(5) C16 0.0434(6) 0.0523(7) 0.0512(7) -0.0019(6) -0.0040(5) 0.0019(5) C17 0.0356(6) 0.0568(7) 0.0640(8) -0.0050(6) -0.0001(5) -0.0014(5) C18 0.0360(6) 0.0491(7) 0.0626(8) -0.0028(6) 0.0129(5) -0.0013(5) C19 0.0340(5) 0.0396(6) 0.0488(6) -0.0024(5) 0.0106(4) 0.0049(4) C20 0.0420(6) 0.0412(6) 0.0495(6) 0.0021(5) 0.0174(5) 0.0017(5) C21 0.0444(6) 0.0419(6) 0.0388(5) 0.0012(5) 0.0124(5) 0.0037(5) C22 0.0369(5) 0.0356(5) 0.0366(5) -0.0007(4) 0.0089(4) 0.0044(4) C23 0.0414(6) 0.0381(5) 0.0310(5) 0.0003(4) 0.0076(4) 0.0026(4) C24 0.0330(5) 0.0375(5) 0.0316(5) -0.0029(4) 0.0029(4) -0.0036(4) C25 0.0390(6) 0.0428(6) 0.0357(5) -0.0028(4) 0.0040(4) 0.0030(4) C26 0.0392(6) 0.0474(6) 0.0537(7) -0.0108(5) 0.0027(5) 0.0039(5) C27 0.0394(6) 0.0576(7) 0.0588(8) -0.0232(6) 0.0161(5) -0.0094(5) C28 0.0541(7) 0.0574(7) 0.0431(6) -0.0121(6) 0.0185(5) -0.0199(6) C29 0.0486(6) 0.0440(6) 0.0355(5) -0.0010(5) 0.0076(5) -0.0093(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C23 1.3148(14) . ? N1 C2 1.3963(14) . ? N1 C11 1.4937(13) . ? C2 C3 1.4394(14) . ? C2 C10 1.4469(15) . ? C3 O3 1.2365(13) . ? C3 C4 1.4912(15) . ? C4 C5 1.3786(16) . ? C4 C9 1.3845(15) . ? C5 C6 1.3928(18) . ? C6 C7 1.3846(19) . ? C7 C8 1.3954(18) . ? C8 C9 1.3789(16) . ? C9 C10 1.5004(15) . ? C10 O10 1.2313(13) . ? C11 C12 1.5267(15) . ? C12 C13 1.5087(15) . ? C12 C24 1.5216(14) . ? C13 C22 1.3861(15) . ? C13 C14 1.4224(15) . ? C14 C15 1.4194(16) . ? C14 C19 1.4267(16) . ? C15 C16 1.3702(17) . ? C16 C17 1.4050(19) . ? C17 C18 1.3627(19) . ? C18 C19 1.4186(17) . ? C19 C20 1.4200(17) . ? C20 C21 1.3574(17) . ? C21 C22 1.4225(15) . ? C22 C23 1.4412(16) . ? C24 C29 1.3906(15) . ? C24 C25 1.3922(15) . ? C25 C26 1.3875(16) . ? C26 C27 1.3847(19) . ? C27 C28 1.378(2) . ? C28 C29 1.3838(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 C23 N1 C2 123.50(9) . . ? C23 N1 C11 117.39(9) . . ? C2 N1 C11 118.92(9) . . ? N1 C2 C3 123.09(9) . . ? N1 C2 C10 127.00(9) . . ? C3 C2 C10 109.91(9) . . ? O3 C3 C2 129.20(10) . . ? O3 C3 C4 124.46(10) . . ? C2 C3 C4 106.34(9) . . ? C5 C4 C9 121.59(11) . . ? C5 C4 C3 129.44(10) . . ? C9 C4 C3 108.97(9) . . ? C4 C5 C6 117.89(11) . . ? C7 C6 C5 120.63(12) . . ? C6 C7 C8 121.09(12) . . ? C9 C8 C7 117.90(11) . . ? C8 C9 C4 120.90(11) . . ? C8 C9 C10 129.89(10) . . ? C4 C9 C10 109.21(10) . . ? O10 C10 C2 131.07(11) . . ? O10 C10 C9 123.36(10) . . ? C2 C10 C9 105.57(9) . . ? N1 C11 C12 112.14(8) . . ? C13 C12 C24 113.25(9) . . ? C13 C12 C11 110.51(9) . . ? C24 C12 C11 112.24(9) . . ? C22 C13 C14 120.01(10) . . ? C22 C13 C12 117.57(9) . . ? C14 C13 C12 122.34(9) . . ? C15 C14 C13 122.64(10) . . ? C15 C14 C19 118.46(10) . . ? C13 C14 C19 118.90(10) . . ? C16 C15 C14 120.83(12) . . ? C15 C16 C17 120.43(12) . . ? C18 C17 C16 120.45(12) . . ? C17 C18 C19 120.88(12) . . ? C18 C19 C20 121.73(11) . . ? C18 C19 C14 118.94(11) . . ? C20 C19 C14 119.33(10) . . ? C21 C20 C19 120.99(11) . . ? C20 C21 C22 120.27(11) . . ? C13 C22 C21 120.47(10) . . ? C13 C22 C23 120.44(10) . . ? C21 C22 C23 118.98(10) . . ? N1 C23 C22 122.75(10) . . ? C29 C24 C25 118.52(10) . . ? C29 C24 C12 118.74(10) . . ? C25 C24 C12 122.70(9) . . ? C26 C25 C24 120.82(11) . . ? C27 C26 C25 119.51(12) . . ? C28 C27 C26 120.42(11) . . ? C27 C28 C29 119.84(12) . . ? C28 C29 C24 120.87(12) . . ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 30.46 _diffrn_measured_fraction_theta_full 0.851 _refine_diff_density_max 0.258 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.062