Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2002 data_2a _database_code_CSD 177486 _journal_coden_Cambridge 568 _publ_requested_journal 'Photochem. and Photobiol. Sciences' loop_ _publ_author_name 'Axel G. Griesbeck' 'Thomas Heinrich' 'Wolfgang Kramer' 'Johann Lex' _publ_contact_author_name 'Prof Axel G. Griesbeck' _publ_contact_author_address ; Chemistry University Cologne Institute of Organic Chemistry Greinstr. 4 Köln D-50939 GERMANY ; _publ_contact_author_email 'GRIESBECK@UNI-KOELN.DE' _publ_section_title ; Photocyclization of N-Phthaloyl Anthranilic Amides Coupled to omega-Amino Acuds With Increasing Chain Lengths ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 414-416 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 N2 O3' _chemical_formula_weight 294.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 11.398(1) _cell_length_b 15.357(1) _cell_length_c 16.312(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2855.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2911 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.096 _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 293(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' _diffrn_measurement_method Phi/Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2911 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2911 _reflns_number_gt 2244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0487P)^2^+0.7538P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2911 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.097 _refine_ls_shift/su_mean 0.013 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 0.19424(10) 0.02309(7) 0.05637(6) 0.0358(3) Uani 1 1 d . . . N2 N 0.14670(10) 0.14941(7) -0.01340(7) 0.0277(3) Uani 1 1 d . . . C3 C 0.28160(12) 0.05819(9) -0.07636(9) 0.0293(3) Uani 1 1 d . . . N4 N 0.28243(12) 0.27675(9) 0.10495(9) 0.0389(3) Uani 1 1 d . . . O5 O 0.15990(11) 0.38628(7) 0.07114(8) 0.0502(3) Uani 1 1 d . . . C6 C 0.06011(12) 0.17450(8) 0.04621(8) 0.0277(3) Uani 1 1 d . . . O7 O 0.03191(11) 0.17999(9) -0.12662(7) 0.0533(3) Uani 1 1 d . . . C8 C 0.31230(14) 0.18755(11) 0.12652(10) 0.0354(4) Uani 1 1 d . . . C9 C -0.04115(13) 0.12507(10) 0.05326(10) 0.0377(4) Uani 1 1 d . . . C10 C 0.07347(12) 0.24888(9) 0.09420(9) 0.0290(3) Uani 1 1 d . . . C11 C 0.11699(13) 0.14510(10) -0.09529(9) 0.0346(4) Uani 1 1 d . . . C12 C 0.24433(12) 0.08949(9) 0.00760(8) 0.0279(3) Uani 1 1 d . . . C13 C 0.34589(13) 0.13327(12) 0.05232(10) 0.0357(4) Uani 1 1 d . . . C14 C -0.11502(14) 0.22215(11) 0.15569(10) 0.0406(4) Uani 1 1 d . . . C15 C 0.17706(13) 0.30857(10) 0.08789(9) 0.0343(4) Uani 1 1 d . . . C16 C 0.20774(13) 0.09100(10) -0.13561(9) 0.0330(3) Uani 1 1 d . . . C17 C -0.01538(14) 0.27204(10) 0.14874(10) 0.0367(4) Uani 1 1 d . . . C18 C 0.37504(14) 0.00563(11) -0.09737(10) 0.0384(4) Uani 1 1 d . . . C19 C 0.39211(15) -0.01308(12) -0.17987(11) 0.0466(4) Uani 1 1 d . . . C20 C 0.22330(16) 0.07165(12) -0.21798(10) 0.0456(4) Uani 1 1 d . . . C21 C 0.31732(16) 0.01959(12) -0.23921(11) 0.0497(5) Uani 1 1 d . . . C22 C -0.12831(15) 0.14888(11) 0.10770(11) 0.0442(4) Uani 1 1 d . . . H1 H 0.2457(14) 0.1607(9) 0.1576(9) 0.031(4) Uiso 1 1 d . . . H2 H 0.3798(15) 0.1908(10) 0.1629(10) 0.037(4) Uiso 1 1 d . . . H3 H 0.4279(16) -0.0194(11) -0.0544(10) 0.047(5) Uiso 1 1 d . . . H4 H -0.0491(15) 0.0735(11) 0.0177(10) 0.049(5) Uiso 1 1 d . . . H5 H -0.0048(14) 0.3245(11) 0.1809(10) 0.044(5) Uiso 1 1 d . . . H6 H -0.1765(16) 0.2392(12) 0.1931(11) 0.052(5) Uiso 1 1 d . . . H7 H -0.1990(16) 0.1138(12) 0.1121(11) 0.051(5) Uiso 1 1 d . . . H8 H 0.3917(16) 0.1684(11) 0.0141(11) 0.050(5) Uiso 1 1 d . . . H9 H 0.4000(17) 0.0862(12) 0.0688(10) 0.051(5) Uiso 1 1 d . . . H10 H 0.4561(16) -0.0493(12) -0.1958(10) 0.050(5) Uiso 1 1 d . . . H11 H 0.1693(16) 0.0957(11) -0.2582(12) 0.057(5) Uiso 1 1 d . . . H12 H 0.244(2) -0.0250(14) 0.0585(12) 0.067(6) Uiso 1 1 d . . . H13 H 0.3414(18) 0.3111(12) 0.0979(12) 0.056(6) Uiso 1 1 d . . . H14 H 0.3324(16) 0.0047(13) -0.2948(12) 0.061(6) 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 0.0402(6) 0.0305(6) 0.0367(6) 0.0061(4) 0.0037(5) 0.0051(5) N2 0.0260(6) 0.0284(6) 0.0287(7) -0.0015(5) -0.0021(5) 0.0035(5) C3 0.0276(7) 0.0289(7) 0.0312(8) -0.0023(6) -0.0008(6) -0.0013(6) N4 0.0320(7) 0.0352(7) 0.0496(9) -0.0063(6) 0.0024(6) -0.0096(6) O5 0.0516(8) 0.0268(6) 0.0723(9) 0.0043(5) 0.0034(6) -0.0072(5) C6 0.0266(7) 0.0254(7) 0.0310(8) 0.0018(5) -0.0002(6) 0.0028(6) O7 0.0457(7) 0.0719(9) 0.0424(7) 0.0040(6) -0.0102(5) 0.0241(6) C8 0.0313(8) 0.0417(9) 0.0333(9) -0.0047(7) -0.0052(7) -0.0003(7) C9 0.0334(8) 0.0301(8) 0.0496(10) -0.0058(7) 0.0001(7) -0.0042(6) C10 0.0309(7) 0.0247(7) 0.0316(8) 0.0016(6) 0.0002(6) -0.0004(6) C11 0.0330(8) 0.0357(8) 0.0350(9) 0.0026(6) -0.0047(6) 0.0023(7) C12 0.0270(7) 0.0280(7) 0.0287(8) 0.0008(6) -0.0009(6) 0.0041(6) C13 0.0266(8) 0.0449(9) 0.0356(9) -0.0067(7) -0.0034(6) 0.0041(7) C14 0.0360(9) 0.0428(9) 0.0431(10) 0.0028(7) 0.0108(7) 0.0026(7) C15 0.0385(9) 0.0299(8) 0.0346(9) -0.0055(6) 0.0047(6) -0.0053(7) C16 0.0338(8) 0.0355(8) 0.0296(9) -0.0008(6) -0.0015(6) 0.0005(6) C17 0.0399(9) 0.0323(8) 0.0380(9) -0.0037(7) 0.0040(7) 0.0010(7) C18 0.0343(8) 0.0429(9) 0.0380(10) -0.0067(7) -0.0001(7) 0.0060(7) C19 0.0398(9) 0.0540(11) 0.0460(11) -0.0124(8) 0.0066(8) 0.0074(8) C20 0.0524(10) 0.0538(11) 0.0307(10) -0.0003(7) -0.0046(8) 0.0046(9) C21 0.0561(11) 0.0603(11) 0.0326(10) -0.0108(8) 0.0064(8) -0.0002(9) C22 0.0318(9) 0.0397(9) 0.0611(12) 0.0014(8) 0.0075(8) -0.0077(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.4138(17) . ? N2 C11 1.3795(19) . ? N2 C6 1.4380(18) . ? N2 C12 1.4840(17) . ? C3 C16 1.377(2) . ? C3 C18 1.380(2) . ? C3 C12 1.512(2) . ? N4 C15 1.326(2) . ? N4 C8 1.455(2) . ? O5 C15 1.2398(18) . ? C6 C9 1.386(2) . ? C6 C10 1.3932(19) . ? O7 C11 1.2202(18) . ? C8 C13 1.519(2) . ? C9 C22 1.382(2) . ? C10 C17 1.394(2) . ? C10 C15 1.498(2) . ? C11 C16 1.481(2) . ? C12 C13 1.524(2) . ? C14 C17 1.375(2) . ? C14 C22 1.379(2) . ? C16 C20 1.388(2) . ? C18 C19 1.390(2) . ? C19 C21 1.384(3) . ? C20 C21 1.381(3) . ? 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 C11 N2 C6 119.94(11) . . ? C11 N2 C12 112.20(11) . . ? C6 N2 C12 121.65(11) . . ? C16 C3 C18 120.77(14) . . ? C16 C3 C12 110.34(12) . . ? C18 C3 C12 128.88(13) . . ? C15 N4 C8 127.56(14) . . ? C9 C6 C10 119.56(13) . . ? C9 C6 N2 118.74(12) . . ? C10 C6 N2 121.65(12) . . ? N4 C8 C13 112.53(14) . . ? C22 C9 C6 120.47(14) . . ? C6 C10 C17 119.24(13) . . ? C6 C10 C15 123.30(12) . . ? C17 C10 C15 117.40(13) . . ? O7 C11 N2 125.42(14) . . ? O7 C11 C16 127.99(14) . . ? N2 C11 C16 106.59(12) . . ? O1 C12 N2 105.92(11) . . ? O1 C12 C3 113.19(11) . . ? N2 C12 C3 101.46(11) . . ? O1 C12 C13 110.82(12) . . ? N2 C12 C13 113.98(12) . . ? C3 C12 C13 111.11(12) . . ? C8 C13 C12 115.59(13) . . ? C17 C14 C22 119.91(15) . . ? O5 C15 N4 122.94(14) . . ? O5 C15 C10 118.66(14) . . ? N4 C15 C10 118.29(13) . . ? C3 C16 C20 121.54(14) . . ? C3 C16 C11 108.70(12) . . ? C20 C16 C11 129.76(14) . . ? C14 C17 C10 120.70(14) . . ? C3 C18 C19 118.01(16) . . ? C18 C19 C21 121.07(16) . . ? C21 C20 C16 117.77(16) . . ? C20 C21 C19 120.83(16) . . ? C9 C22 C14 120.12(15) . . ? 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 C11 N2 C6 C9 59.09(18) . . . . ? C12 N2 C6 C9 -91.04(16) . . . . ? C11 N2 C6 C10 -118.17(15) . . . . ? C12 N2 C6 C10 91.70(16) . . . . ? C15 N4 C8 C13 92.32(19) . . . . ? C10 C6 C9 C22 -0.3(2) . . . . ? N2 C6 C9 C22 -177.63(14) . . . . ? C9 C6 C10 C17 0.2(2) . . . . ? N2 C6 C10 C17 177.47(13) . . . . ? C9 C6 C10 C15 -176.96(14) . . . . ? N2 C6 C10 C15 0.3(2) . . . . ? C6 N2 C11 O7 18.6(2) . . . . ? C12 N2 C11 O7 171.37(15) . . . . ? C6 N2 C11 C16 -161.50(12) . . . . ? C12 N2 C11 C16 -8.75(16) . . . . ? C11 N2 C12 O1 -110.21(12) . . . . ? C6 N2 C12 O1 42.01(15) . . . . ? C11 N2 C12 C3 8.19(15) . . . . ? C6 N2 C12 C3 160.41(12) . . . . ? C11 N2 C12 C13 127.69(13) . . . . ? C6 N2 C12 C13 -80.09(16) . . . . ? C16 C3 C12 O1 108.61(14) . . . . ? C18 C3 C12 O1 -72.29(19) . . . . ? C16 C3 C12 N2 -4.42(15) . . . . ? C18 C3 C12 N2 174.68(15) . . . . ? C16 C3 C12 C13 -125.94(14) . . . . ? C18 C3 C12 C13 53.2(2) . . . . ? N4 C8 C13 C12 -86.99(18) . . . . ? O1 C12 C13 C8 -68.58(17) . . . . ? N2 C12 C13 C8 50.78(19) . . . . ? C3 C12 C13 C8 164.67(14) . . . . ? C8 N4 C15 O5 178.99(15) . . . . ? C8 N4 C15 C10 2.8(2) . . . . ? C6 C10 C15 O5 121.66(16) . . . . ? C17 C10 C15 O5 -55.6(2) . . . . ? C6 C10 C15 N4 -62.0(2) . . . . ? C17 C10 C15 N4 120.76(16) . . . . ? C18 C3 C16 C20 0.9(2) . . . . ? C12 C3 C16 C20 -179.91(15) . . . . ? C18 C3 C16 C11 -179.61(14) . . . . ? C12 C3 C16 C11 -0.43(17) . . . . ? O7 C11 C16 C3 -174.54(16) . . . . ? N2 C11 C16 C3 5.58(17) . . . . ? O7 C11 C16 C20 4.9(3) . . . . ? N2 C11 C16 C20 -174.99(16) . . . . ? C22 C14 C17 C10 -0.7(2) . . . . ? C6 C10 C17 C14 0.3(2) . . . . ? C15 C10 C17 C14 177.65(14) . . . . ? C16 C3 C18 C19 0.0(2) . . . . ? C12 C3 C18 C19 -179.05(15) . . . . ? C3 C18 C19 C21 -0.3(3) . . . . ? C3 C16 C20 C21 -1.4(3) . . . . ? C11 C16 C20 C21 179.28(16) . . . . ? C16 C20 C21 C19 1.0(3) . . . . ? C18 C19 C21 C20 -0.1(3) . . . . ? C6 C9 C22 C14 -0.1(3) . . . . ? C17 C14 C22 C9 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.132 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.041