# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/443 data_in2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H25 N3' _chemical_formula_sum 'C28 H25 N3' _chemical_formula_weight 403.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, -z' 'x+1/2, -y+1/2, z' 'x, y+1/2, -z' _cell_length_a 9.527(2) _cell_length_b 12.367(5) _cell_length_c 18.594(7) _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(2) _cell_volume 2190.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 20 _cell_measurement_theta_max 60 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.557 _exptl_absorpt_correction_type no _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Ni filter used ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator no _diffrn_measurement_device_type ; Stoe four circle diffractometer, microVAX controlled ; _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 3 _diffrn_reflns_number 2058 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 67.06 _reflns_number_total 2058 _reflns_number_gt 1613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE software' _computing_cell_refinement 'STOE software' _computing_data_reduction 'Stoe-routine REDUC' _computing_structure_solution 'SIR92 (Altomare, 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SCHAKAL88 (Keller, 1988); ORTEPII (Johnson, 1976) ; _computing_publication_material ; SHELXL-93_ACTA (Sheldrick, 1993) ; _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^)+(0.0611P)^2^+0.3713P] 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 SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(11) _refine_ls_number_reflns 2058 _refine_ls_number_parameters 370 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.003 _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 0.4035(5) 0.2624(3) 0.2515(2) 0.0515(9) Uani 1 1 d . . . H1 H 0.299(5) 0.271(3) 0.2507(16) 0.039(9) Uiso 1 1 d . . . C2 C 0.4450(4) 0.2270(3) 0.32631(19) 0.0519(9) Uani 1 1 d . . . C3 C 0.5273(5) 0.2825(3) 0.3730(2) 0.0591(10) Uani 1 1 d . . . H3 H 0.571(5) 0.349(3) 0.364(2) 0.061(12) Uiso 1 1 d . . . N4 N 0.5386(4) 0.2296(2) 0.43810(15) 0.0565(8) Uani 1 1 d . . . C41 C 0.6130(7) 0.2702(4) 0.5002(3) 0.0689(13) Uani 1 1 d . . . H41A H 0.568(7) 0.268(4) 0.540(3) 0.087(19) Uiso 1 1 d . . . H41B H 0.612(7) 0.344(5) 0.499(3) 0.104(18) Uiso 1 1 d . . . H41C H 0.685(8) 0.224(5) 0.512(3) 0.13(3) Uiso 1 1 d . . . C5 C 0.4599(4) 0.1366(3) 0.4343(2) 0.0530(9) Uani 1 1 d . . . C6 C 0.4355(5) 0.0577(3) 0.4859(2) 0.0623(11) Uani 1 1 d . . . H6 H 0.486(5) 0.067(3) 0.528(2) 0.052(11) Uiso 1 1 d . . . C7 C 0.3473(6) -0.0254(4) 0.4686(3) 0.0712(13) Uani 1 1 d . . . H7 H 0.325(5) -0.082(4) 0.503(2) 0.077(14) Uiso 1 1 d . . . C8 C 0.2865(6) -0.0326(3) 0.3997(3) 0.0657(11) Uani 1 1 d . . . H8 H 0.217(5) -0.090(3) 0.389(2) 0.068(12) Uiso 1 1 d . . . C9 C 0.3124(5) 0.0438(3) 0.3473(2) 0.0579(11) Uani 1 1 d . . . H9 H 0.262(6) 0.043(4) 0.299(3) 0.086(16) Uiso 1 1 d . . . C10 C 0.4013(4) 0.1316(3) 0.3643(2) 0.0493(9) Uani 1 1 d . . . C11 C 0.4571(4) 0.3762(3) 0.23622(19) 0.0528(9) Uani 1 1 d . . . C12 C 0.5651(5) 0.4050(3) 0.1925(2) 0.0567(10) Uani 1 1 d . . . H12 H 0.620(6) 0.365(4) 0.160(3) 0.088(16) Uiso 1 1 d . . . N13 N 0.5858(4) 0.5162(3) 0.1946(2) 0.0673(9) Uani 1 1 d . . . C131 C 0.6993(8) 0.5734(6) 0.1590(4) 0.0876(17) Uani 1 1 d . . . H13A H 0.645(9) 0.644(6) 0.130(4) 0.17(3) Uiso 1 1 d . . . H13B H 0.745(7) 0.532(5) 0.122(4) 0.12(3) Uiso 1 1 d . . . H13C H 0.766(10) 0.601(6) 0.187(4) 0.15(3) Uiso 1 1 d . . . C14 C 0.4891(5) 0.5592(3) 0.2420(2) 0.0674(12) Uani 1 1 d . . . C15 C 0.4686(9) 0.6669(4) 0.2622(3) 0.0938(19) Uani 1 1 d . . . H15 H 0.550(7) 0.720(4) 0.249(2) 0.101(18) Uiso 1 1 d . . . C16 C 0.3613(10) 0.6861(6) 0.3090(4) 0.113(2) Uani 1 1 d . . . H16 H 0.356(6) 0.763(5) 0.325(2) 0.096(16) Uiso 1 1 d . . . C17 C 0.2788(10) 0.6035(6) 0.3359(3) 0.107(2) Uani 1 1 d . . . H17 H 0.205(7) 0.616(4) 0.363(3) 0.09(2) Uiso 1 1 d . . . C18 C 0.3004(7) 0.4964(5) 0.3175(3) 0.0771(14) Uani 1 1 d . . . H18 H 0.237(5) 0.438(4) 0.344(2) 0.068(13) Uiso 1 1 d . . . C19 C 0.4067(5) 0.4742(3) 0.2689(2) 0.0583(11) Uani 1 1 d . . . C20 C 0.4486(4) 0.1843(3) 0.1929(2) 0.0537(9) Uani 1 1 d . . . C21 C 0.5255(5) 0.0928(4) 0.2015(3) 0.0662(11) Uani 1 1 d . . . H21 H 0.565(5) 0.067(3) 0.248(2) 0.069(13) Uiso 1 1 d . . . N22 N 0.5468(4) 0.0423(3) 0.1359(2) 0.0739(11) Uani 1 1 d . . . C221 C 0.6239(8) -0.0571(5) 0.1258(4) 0.116(2) Uani 1 1 d . . . H22A H 0.5611 -0.1127 0.1095 0.174 Uiso 1 1 calc R . . H22B H 0.6656 -0.0786 0.1706 0.174 Uiso 1 1 calc R . . H22C H 0.6963 -0.0462 0.0906 0.174 Uiso 1 1 calc R . . C23 C 0.4831(5) 0.1033(4) 0.0838(2) 0.0684(12) Uani 1 1 d . . . C24 C 0.4766(7) 0.0876(6) 0.0099(3) 0.096(2) Uani 1 1 d . . . H24 H 0.509(10) 0.030(6) -0.017(4) 0.16(3) Uiso 1 1 d . . . C25 C 0.4057(8) 0.1645(8) -0.0303(3) 0.108(2) Uani 1 1 d . . . H25 H 0.401(8) 0.146(5) -0.082(4) 0.14(2) Uiso 1 1 d . . . C26 C 0.3403(7) 0.2514(8) 0.0020(3) 0.1043(19) Uani 1 1 d . . . H26 H 0.281(9) 0.307(5) -0.033(4) 0.14(3) Uiso 1 1 d . . . C27 C 0.3449(6) 0.2666(5) 0.0756(3) 0.0828(15) Uani 1 1 d . . . H27 H 0.303(6) 0.327(4) 0.099(3) 0.086(17) Uiso 1 1 d . . . C28 C 0.4196(5) 0.1921(3) 0.1179(2) 0.0611(11) 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 0.050(2) 0.053(2) 0.0512(19) -0.0003(18) 0.0011(19) 0.0020(19) C2 0.052(2) 0.052(2) 0.0519(19) 0.0008(16) 0.0012(19) -0.002(2) C3 0.060(2) 0.055(2) 0.063(2) 0.0077(19) -0.004(2) -0.010(2) N4 0.064(2) 0.0537(18) 0.0518(16) 0.0027(14) -0.0120(18) -0.0054(17) C41 0.082(3) 0.060(3) 0.065(3) -0.001(2) -0.019(3) -0.001(3) C5 0.050(2) 0.0460(19) 0.063(2) -0.0002(16) -0.003(2) 0.0045(19) C6 0.066(3) 0.057(2) 0.063(3) 0.0103(19) -0.006(2) 0.004(2) C7 0.082(3) 0.054(2) 0.078(3) 0.014(2) 0.003(3) -0.003(3) C8 0.067(3) 0.046(2) 0.084(3) 0.001(2) 0.004(3) -0.011(2) C9 0.062(3) 0.051(2) 0.060(2) -0.0037(19) -0.003(2) -0.002(2) C10 0.049(2) 0.0459(18) 0.053(2) -0.0027(16) 0.0051(18) 0.0033(18) C11 0.054(2) 0.0515(19) 0.053(2) 0.0013(16) -0.006(2) 0.003(2) C12 0.057(3) 0.058(2) 0.056(2) 0.0026(19) 0.001(2) 0.006(2) N13 0.072(2) 0.0562(19) 0.074(2) 0.0164(17) -0.004(2) -0.004(2) C131 0.087(4) 0.086(4) 0.090(4) 0.021(4) 0.000(4) -0.022(4) C14 0.081(3) 0.060(2) 0.061(2) 0.004(2) -0.012(2) 0.007(2) C15 0.131(6) 0.055(3) 0.096(4) 0.002(3) -0.021(4) 0.004(4) C16 0.161(7) 0.075(4) 0.101(5) -0.021(3) -0.008(5) 0.033(5) C17 0.133(6) 0.110(5) 0.080(4) -0.023(3) 0.004(4) 0.047(5) C18 0.089(3) 0.085(3) 0.058(3) -0.004(2) -0.001(3) 0.025(3) C19 0.070(3) 0.053(2) 0.052(2) 0.0020(17) -0.006(2) 0.007(2) C20 0.053(2) 0.055(2) 0.053(2) -0.0009(16) -0.005(2) -0.004(2) C21 0.066(3) 0.068(3) 0.065(3) -0.006(2) -0.002(2) 0.007(2) N22 0.074(3) 0.072(2) 0.076(2) -0.0158(19) 0.009(2) 0.007(2) C221 0.122(5) 0.094(4) 0.132(6) -0.033(4) 0.015(5) 0.032(4) C23 0.064(3) 0.080(3) 0.061(2) -0.012(2) 0.006(2) -0.008(2) C24 0.084(4) 0.133(5) 0.072(4) -0.034(4) 0.014(3) -0.030(4) C25 0.092(4) 0.173(7) 0.059(3) -0.015(4) -0.004(4) -0.030(5) C26 0.101(4) 0.149(5) 0.063(3) 0.010(4) -0.017(4) -0.011(4) C27 0.078(3) 0.104(4) 0.067(3) 0.007(3) -0.012(3) 0.000(3) C28 0.053(3) 0.068(2) 0.062(2) -0.003(2) 0.000(2) -0.006(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 C1 C2 1.510(5) . ? C1 C20 1.519(5) . ? C1 C11 1.524(5) . ? C1 H1 1.01(4) . ? C2 C3 1.356(5) . ? C2 C10 1.436(5) . ? C3 N4 1.380(5) . ? C3 H3 0.93(4) . ? N4 C5 1.376(5) . ? N4 C41 1.446(5) . ? C41 H41A 0.85(5) . ? C41 H41B 0.92(6) . ? C41 H41C 0.92(8) . ? C5 C6 1.388(5) . ? C5 C10 1.417(5) . ? C6 C7 1.366(6) . ? C6 H6 0.93(4) . ? C7 C8 1.409(7) . ? C7 H7 0.97(5) . ? C8 C9 1.379(6) . ? C8 H8 0.99(5) . ? C9 C10 1.413(6) . ? C9 H9 1.02(5) . ? C11 C12 1.358(6) . ? C11 C19 1.438(5) . ? C12 N13 1.391(5) . ? C12 H12 0.94(5) . ? N13 C14 1.382(6) . ? N13 C131 1.451(7) . ? C131 H13A 1.15(8) . ? C131 H13B 0.96(6) . ? C131 H13C 0.89(9) . ? C14 C15 1.398(6) . ? C14 C19 1.403(6) . ? C15 C16 1.364(10) . ? C15 H15 1.04(6) . ? C16 C17 1.382(11) . ? C16 H16 1.00(6) . ? C17 C18 1.383(8) . ? C17 H17 0.88(6) . ? C18 C19 1.385(7) . ? C18 H18 1.07(5) . ? C20 C21 1.358(6) . ? C20 C28 1.424(6) . ? C21 N22 1.385(6) . ? C21 H21 0.99(4) . ? N22 C23 1.370(6) . ? N22 C221 1.445(7) . ? C221 H22A 0.9600 . ? C221 H22B 0.9600 . ? C221 H22C 0.9600 . ? C23 C24 1.389(7) . ? C23 C28 1.405(6) . ? C24 C25 1.386(10) . ? C24 H24 0.92(8) . ? C25 C26 1.380(11) . ? C25 H25 1.00(7) . ? C26 C27 1.381(7) . ? C26 H26 1.10(8) . ? C27 C28 1.406(7) . ? C27 H27 0.95(5) . ? 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 C20 113.8(3) . . ? C2 C1 C11 110.6(3) . . ? C20 C1 C11 111.0(3) . . ? C2 C1 H1 107.8(18) . . ? C20 C1 H1 109.7(19) . . ? C11 C1 H1 103(2) . . ? C3 C2 C10 105.5(3) . . ? C3 C2 C1 126.4(3) . . ? C10 C2 C1 128.0(3) . . ? C2 C3 N4 111.5(3) . . ? C2 C3 H3 126(3) . . ? N4 C3 H3 123(3) . . ? C5 N4 C3 107.9(3) . . ? C5 N4 C41 126.8(3) . . ? C3 N4 C41 125.1(4) . . ? N4 C41 H41A 115(4) . . ? N4 C41 H41B 109(4) . . ? H41A C41 H41B 93(5) . . ? N4 C41 H41C 110(4) . . ? H41A C41 H41C 98(5) . . ? H41B C41 H41C 129(6) . . ? N4 C5 C6 130.0(4) . . ? N4 C5 C10 107.4(3) . . ? C6 C5 C10 122.6(4) . . ? C7 C6 C5 118.0(4) . . ? C7 C6 H6 127(2) . . ? C5 C6 H6 115(2) . . ? C6 C7 C8 120.9(4) . . ? C6 C7 H7 121(3) . . ? C8 C7 H7 118(3) . . ? C9 C8 C7 121.7(4) . . ? C9 C8 H8 118(3) . . ? C7 C8 H8 120(2) . . ? C8 C9 C10 118.4(4) . . ? C8 C9 H9 122(3) . . ? C10 C9 H9 119(3) . . ? C9 C10 C5 118.3(4) . . ? C9 C10 C2 134.0(4) . . ? C5 C10 C2 107.6(3) . . ? C12 C11 C19 106.6(3) . . ? C12 C11 C1 127.4(3) . . ? C19 C11 C1 126.0(4) . . ? C11 C12 N13 110.5(4) . . ? C11 C12 H12 132(3) . . ? N13 C12 H12 117(3) . . ? C14 N13 C12 107.6(4) . . ? C14 N13 C131 126.9(4) . . ? C12 N13 C131 125.1(5) . . ? N13 C131 H13A 104(4) . . ? N13 C131 H13B 114(4) . . ? H13A C131 H13B 106(5) . . ? N13 C131 H13C 117(5) . . ? H13A C131 H13C 108(6) . . ? H13B C131 H13C 107(7) . . ? N13 C14 C15 129.1(5) . . ? N13 C14 C19 108.2(4) . . ? C15 C14 C19 122.7(5) . . ? C16 C15 C14 116.2(6) . . ? C16 C15 H15 127(3) . . ? C14 C15 H15 116(3) . . ? C15 C16 C17 122.0(6) . . ? C15 C16 H16 113(3) . . ? C17 C16 H16 125(3) . . ? C16 C17 C18 122.2(7) . . ? C16 C17 H17 122(4) . . ? C18 C17 H17 115(4) . . ? C19 C18 C17 117.4(6) . . ? C19 C18 H18 126(2) . . ? C17 C18 H18 117(2) . . ? C18 C19 C14 119.6(4) . . ? C18 C19 C11 133.4(4) . . ? C14 C19 C11 107.0(4) . . ? C21 C20 C28 106.1(4) . . ? C21 C20 C1 126.7(4) . . ? C28 C20 C1 127.2(4) . . ? C20 C21 N22 110.6(4) . . ? C20 C21 H21 125(3) . . ? N22 C21 H21 124(3) . . ? C23 N22 C21 108.0(4) . . ? C23 N22 C221 127.0(5) . . ? C21 N22 C221 125.0(5) . . ? N22 C221 H22A 109.5 . . ? N22 C221 H22B 109.5 . . ? H22A C221 H22B 109.5 . . ? N22 C221 H22C 109.5 . . ? H22A C221 H22C 109.5 . . ? H22B C221 H22C 109.5 . . ? N22 C23 C24 130.0(5) . . ? N22 C23 C28 107.5(4) . . ? C24 C23 C28 122.5(5) . . ? C25 C24 C23 117.4(6) . . ? C25 C24 H24 114(5) . . ? C23 C24 H24 129(5) . . ? C26 C25 C24 121.3(6) . . ? C26 C25 H25 126(4) . . ? C24 C25 H25 113(4) . . ? C27 C26 C25 121.6(7) . . ? C27 C26 H26 121(4) . . ? C25 C26 H26 118(3) . . ? C26 C27 C28 118.8(7) . . ? C26 C27 H27 124(3) . . ? C28 C27 H27 117(3) . . ? C27 C28 C23 118.5(4) . . ? C27 C28 C20 133.7(4) . . ? C23 C28 C20 107.8(4) . . ? 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 C20 C1 C2 C3 120.9(4) . . . . ? C11 C1 C2 C3 -4.8(6) . . . . ? C20 C1 C2 C10 -62.3(5) . . . . ? C11 C1 C2 C10 171.9(4) . . . . ? C10 C2 C3 N4 -0.4(5) . . . . ? C1 C2 C3 N4 177.0(4) . . . . ? C2 C3 N4 C5 -0.5(5) . . . . ? C2 C3 N4 C41 -176.7(5) . . . . ? C3 N4 C5 C6 -178.6(4) . . . . ? C41 N4 C5 C6 -2.5(7) . . . . ? C3 N4 C5 C10 1.2(4) . . . . ? C41 N4 C5 C10 177.3(5) . . . . ? N4 C5 C6 C7 177.3(4) . . . . ? C10 C5 C6 C7 -2.5(6) . . . . ? C5 C6 C7 C8 2.0(7) . . . . ? C6 C7 C8 C9 -0.5(8) . . . . ? C7 C8 C9 C10 -0.6(7) . . . . ? C8 C9 C10 C5 0.2(6) . . . . ? C8 C9 C10 C2 -175.9(4) . . . . ? N4 C5 C10 C9 -178.5(4) . . . . ? C6 C5 C10 C9 1.3(6) . . . . ? N4 C5 C10 C2 -1.4(4) . . . . ? C6 C5 C10 C2 178.4(4) . . . . ? C3 C2 C10 C9 177.5(5) . . . . ? C1 C2 C10 C9 0.2(7) . . . . ? C3 C2 C10 C5 1.1(4) . . . . ? C1 C2 C10 C5 -176.2(4) . . . . ? C2 C1 C11 C12 106.8(5) . . . . ? C20 C1 C11 C12 -20.5(6) . . . . ? C2 C1 C11 C19 -69.5(5) . . . . ? C20 C1 C11 C19 163.2(4) . . . . ? C19 C11 C12 N13 -0.8(5) . . . . ? C1 C11 C12 N13 -177.7(4) . . . . ? C11 C12 N13 C14 0.9(5) . . . . ? C11 C12 N13 C131 174.7(5) . . . . ? C12 N13 C14 C15 180.0(5) . . . . ? C131 N13 C14 C15 6.3(8) . . . . ? C12 N13 C14 C19 -0.7(5) . . . . ? C131 N13 C14 C19 -174.3(5) . . . . ? N13 C14 C15 C16 178.1(5) . . . . ? C19 C14 C15 C16 -1.2(8) . . . . ? C14 C15 C16 C17 1.0(10) . . . . ? C15 C16 C17 C18 0.5(11) . . . . ? C16 C17 C18 C19 -1.7(9) . . . . ? C17 C18 C19 C14 1.5(7) . . . . ? C17 C18 C19 C11 -178.1(5) . . . . ? N13 C14 C19 C18 -179.5(4) . . . . ? C15 C14 C19 C18 -0.1(7) . . . . ? N13 C14 C19 C11 0.2(5) . . . . ? C15 C14 C19 C11 179.6(5) . . . . ? C12 C11 C19 C18 180.0(5) . . . . ? C1 C11 C19 C18 -3.1(7) . . . . ? C12 C11 C19 C14 0.3(4) . . . . ? C1 C11 C19 C14 177.3(4) . . . . ? C2 C1 C20 C21 -3.5(6) . . . . ? C11 C1 C20 C21 122.0(5) . . . . ? C2 C1 C20 C28 176.8(4) . . . . ? C11 C1 C20 C28 -57.7(5) . . . . ? C28 C20 C21 N22 0.1(5) . . . . ? C1 C20 C21 N22 -179.7(4) . . . . ? C20 C21 N22 C23 0.5(6) . . . . ? C20 C21 N22 C221 -179.7(5) . . . . ? C21 N22 C23 C24 179.0(5) . . . . ? C221 N22 C23 C24 -0.8(9) . . . . ? C21 N22 C23 C28 -0.8(5) . . . . ? C221 N22 C23 C28 179.4(5) . . . . ? N22 C23 C24 C25 -179.0(5) . . . . ? C28 C23 C24 C25 0.8(8) . . . . ? C23 C24 C25 C26 -2.0(9) . . . . ? C24 C25 C26 C27 1.2(11) . . . . ? C25 C26 C27 C28 0.8(10) . . . . ? C26 C27 C28 C23 -1.9(8) . . . . ? C26 C27 C28 C20 178.2(5) . . . . ? N22 C23 C28 C27 -179.1(4) . . . . ? C24 C23 C28 C27 1.1(7) . . . . ? N22 C23 C28 C20 0.9(5) . . . . ? C24 C23 C28 C20 -178.9(4) . . . . ? C21 C20 C28 C27 179.3(5) . . . . ? C1 C20 C28 C27 -0.9(8) . . . . ? C21 C20 C28 C23 -0.6(5) . . . . ? C1 C20 C28 C23 179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 67.06 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.140 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.032 #======================================================================= # 1. SUBMISSION DETAILS _publ_requested_journal 'J. Chem. Soc. Perkin Translation 1' _publ_requested_coeditor_name ? _publ_contact_author ; Prof. Peter Luger Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; _publ_contact_author_phone '0049-030-83853411' _publ_contact_author_fax '0049-030-83853464' _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_letter ; This material is intended solely for deposition ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of Novel 1-Methylindole Trimer and Tetramer Under Friedel-Crafts Reaction Conditions and Determination of their Structures by X-Ray Crystallography. ; loop_ _publ_author_name _publ_author_address 'Luger, Peter' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Weber, Manuela' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Mahato, Shashi B.' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 Indian ; 'Garai, Subhadra' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; #======================================================================= # 4. TEXT _publ_section_abstract ; ... and following paragraphs: see the published paper. ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #end of data data_in1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H30 N4' _chemical_formula_sum 'C36 H30 N4' _chemical_formula_weight 518.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p1bar' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.595(5) _cell_length_b 11.125(4) _cell_length_c 13.0200(10) _cell_angle_alpha 78.57(6) _cell_angle_beta 68.32(6) _cell_angle_gamma 86.25(3) _cell_volume 1397.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 20 _cell_measurement_theta_max 50 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.565 _exptl_absorpt_correction_type no _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Ni filter used ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator no _diffrn_measurement_device_type ; Stoe four circle diffractometer, microVAX controlled ; _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 4 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 3 _diffrn_reflns_number 5024 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0975 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 65.02 _reflns_number_total 4700 _reflns_number_gt 2653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE software' _computing_cell_refinement 'STOE software' _computing_data_reduction 'Stoe-routine REDUC' _computing_structure_solution 'SIR92 (Altomare, 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SCHAKAL88 (Keller, 1988); ORTEPII (Johnson, 1976) ; _computing_publication_material ; SHELXL-93_ACTA (Sheldrick, 1993) ; _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^)+(0.0737P)^2^+0.1733P] 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 SHELXL _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4700 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1588 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1630 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.9376(3) 0.3604(3) -0.0773(3) 0.0393(8) Uani 1 1 d . . . N2 N 0.8131(3) 0.3953(2) -0.0880(2) 0.0458(7) Uani 1 1 d . . . C2 C 0.7897(4) 0.5045(4) -0.1616(3) 0.0685(12) Uani 1 1 d . . . H2A H 0.7453 0.4814 -0.2072 0.103 Uiso 1 1 calc R . . H2B H 0.8750 0.5436 -0.2092 0.103 Uiso 1 1 calc R . . H2C H 0.7332 0.5604 -0.1168 0.103 Uiso 1 1 calc R . . C3 C 0.7114(3) 0.3297(3) 0.0014(3) 0.0429(8) Uani 1 1 d . . . C4 C 0.5713(3) 0.3310(3) 0.0261(3) 0.0505(9) Uani 1 1 d . . . H4 H 0.5330 0.3841 -0.0190 0.061 Uiso 1 1 calc R . . C5 C 0.4920(3) 0.2506(3) 0.1195(3) 0.0589(10) Uani 1 1 d . . . H5 H 0.3986 0.2487 0.1375 0.071 Uiso 1 1 calc R . . C6 C 0.5497(3) 0.1714(3) 0.1881(3) 0.0552(10) Uani 1 1 d . . . H6 H 0.4938 0.1182 0.2508 0.066 Uiso 1 1 calc R . . C7 C 0.6875(3) 0.1714(3) 0.1642(3) 0.0458(8) Uani 1 1 d . . . H7 H 0.7245 0.1187 0.2105 0.055 Uiso 1 1 calc R . . C8 C 0.7715(3) 0.2513(3) 0.0697(3) 0.0387(8) Uani 1 1 d . . . C9 C 0.9161(3) 0.2717(3) 0.0175(2) 0.0365(7) Uani 1 1 d . . . C10 C 1.0176(3) 0.2068(3) 0.0607(3) 0.0354(7) Uani 1 1 d . . . C11 C 1.1307(3) 0.1431(3) 0.0043(3) 0.0379(8) Uani 1 1 d . . . N12 N 1.1953(3) 0.0923(2) 0.0790(2) 0.0428(7) Uani 1 1 d . . . C12 C 1.2994(3) -0.0027(3) 0.0614(3) 0.0581(10) Uani 1 1 d . . . H12A H 1.3736 0.0210 0.0789 0.087 Uiso 1 1 calc R . . H12B H 1.3317 -0.0125 -0.0157 0.087 Uiso 1 1 calc R . . H12C H 1.2611 -0.0788 0.1096 0.087 Uiso 1 1 calc R . . C13 C 1.1244(3) 0.1230(3) 0.1823(3) 0.0430(8) Uani 1 1 d . . . C14 C 1.1497(4) 0.0948(3) 0.2818(3) 0.0553(10) Uani 1 1 d . . . H14 H 1.2215 0.0445 0.2872 0.066 Uiso 1 1 calc R . . C15 C 1.0645(4) 0.1439(4) 0.3723(3) 0.0648(11) Uani 1 1 d . . . H15 H 1.0795 0.1268 0.4397 0.078 Uiso 1 1 calc R . . C16 C 0.9560(4) 0.2189(4) 0.3642(3) 0.0609(10) Uani 1 1 d . . . H16 H 0.9012 0.2521 0.4260 0.073 Uiso 1 1 calc R . . C17 C 0.9289(3) 0.2444(3) 0.2669(3) 0.0462(8) Uani 1 1 d . . . H17 H 0.8559 0.2938 0.2629 0.055 Uiso 1 1 calc R . . C18 C 1.0123(3) 0.1952(3) 0.1735(3) 0.0393(8) Uani 1 1 d . . . C19 C 1.1900(3) 0.1328(3) -0.1140(3) 0.0384(8) Uani 1 1 d . . . C20 C 1.1265(3) 0.1025(3) -0.1785(3) 0.0432(8) Uani 1 1 d . . . H20 H 1.0352 0.0807 -0.1522 0.052 Uiso 1 1 calc R . . N21 N 1.2139(3) 0.1082(3) -0.2877(2) 0.0510(8) Uani 1 1 d . . . C21 C 1.1815(5) 0.0794(4) -0.3790(3) 0.0748(13) Uani 1 1 d . . . H21A H 1.0859 0.0629 -0.3536 0.112 Uiso 1 1 calc R . . H21B H 1.2314 0.0084 -0.4030 0.112 Uiso 1 1 calc R . . H21C H 1.2058 0.1477 -0.4408 0.112 Uiso 1 1 calc R . . C22 C 1.3389(4) 0.1445(3) -0.2953(3) 0.0483(9) Uani 1 1 d . . . C23 C 1.4611(5) 0.1623(4) -0.3883(3) 0.0716(12) Uani 1 1 d . . . H23 H 1.4665 0.1499 -0.4583 0.086 Uiso 1 1 calc R . . C24 C 1.5716(5) 0.1984(4) -0.3723(5) 0.0888(16) Uani 1 1 d . . . H24 H 1.6540 0.2102 -0.4327 0.107 Uiso 1 1 calc R . . C25 C 1.5647(4) 0.2180(4) -0.2678(5) 0.0834(15) Uani 1 1 d . . . H25 H 1.6421 0.2433 -0.2600 0.100 Uiso 1 1 calc R . . C26 C 1.4448(4) 0.2005(3) -0.1763(4) 0.0619(11) Uani 1 1 d . . . H26 H 1.4407 0.2141 -0.1069 0.074 Uiso 1 1 calc R . . C27 C 1.3289(3) 0.1618(3) -0.1887(3) 0.0447(8) Uani 1 1 d . . . C28 C 1.0652(3) 0.4113(3) -0.1645(3) 0.0401(8) Uani 1 1 d . . . C29 C 1.1715(3) 0.4559(3) -0.1502(3) 0.0455(8) Uani 1 1 d . . . H29 H 1.1743 0.4617 -0.0808 0.055 Uiso 1 1 calc R . . N30 N 1.2747(3) 0.4915(3) -0.2512(2) 0.0490(7) Uani 1 1 d . . . C30 C 1.4070(4) 0.5392(4) -0.2676(4) 0.0690(12) Uani 1 1 d . . . H30A H 1.4758 0.4805 -0.2949 0.103 Uiso 1 1 calc R . . H30B H 1.4069 0.5537 -0.1973 0.103 Uiso 1 1 calc R . . H30C H 1.4256 0.6147 -0.3214 0.103 Uiso 1 1 calc R . . C31 C 1.2357(3) 0.4687(3) -0.3346(3) 0.0485(9) Uani 1 1 d . . . C32 C 1.3025(4) 0.4909(4) -0.4515(3) 0.0645(11) Uani 1 1 d . . . H32 H 1.3878 0.5283 -0.4847 0.077 Uiso 1 1 calc R . . C33 C 1.2394(5) 0.4562(4) -0.5158(4) 0.0787(13) Uani 1 1 d . . . H33 H 1.2825 0.4702 -0.5936 0.094 Uiso 1 1 calc R . . C34 C 1.1122(4) 0.4004(4) -0.4668(3) 0.0708(12) Uani 1 1 d . . . H34 H 1.0724 0.3760 -0.5122 0.085 Uiso 1 1 calc R . . C35 C 1.0434(4) 0.3805(3) -0.3512(3) 0.0573(10) Uani 1 1 d . . . H35 H 0.9577 0.3440 -0.3193 0.069 Uiso 1 1 calc R . . C36 C 1.1040(3) 0.4158(3) -0.2835(3) 0.0445(8) 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 0.0365(18) 0.0349(18) 0.0417(18) -0.0015(14) -0.0119(15) 0.0027(14) N2 0.0412(16) 0.0451(16) 0.0475(16) 0.0055(13) -0.0206(13) 0.0090(13) C2 0.059(2) 0.063(3) 0.068(3) 0.019(2) -0.022(2) 0.017(2) C3 0.0381(18) 0.0408(19) 0.048(2) -0.0045(16) -0.0174(16) 0.0069(15) C4 0.041(2) 0.046(2) 0.068(2) -0.0067(18) -0.0273(18) 0.0084(16) C5 0.0324(18) 0.051(2) 0.089(3) -0.009(2) -0.0193(19) 0.0034(16) C6 0.044(2) 0.042(2) 0.069(2) -0.0026(18) -0.0125(18) -0.0009(16) C7 0.0425(19) 0.0366(18) 0.052(2) 0.0004(16) -0.0156(16) 0.0050(15) C8 0.0366(17) 0.0355(18) 0.0447(19) -0.0054(15) -0.0174(15) 0.0051(14) C9 0.0330(16) 0.0376(18) 0.0383(17) -0.0050(14) -0.0139(14) 0.0039(13) C10 0.0325(16) 0.0298(17) 0.0422(18) -0.0023(14) -0.0142(14) 0.0004(13) C11 0.0376(18) 0.0380(18) 0.0388(18) -0.0031(14) -0.0171(15) 0.0024(14) N12 0.0400(15) 0.0466(16) 0.0452(16) -0.0070(13) -0.0219(13) 0.0115(12) C12 0.054(2) 0.055(2) 0.068(2) -0.0082(19) -0.030(2) 0.0216(18) C13 0.0427(19) 0.043(2) 0.043(2) -0.0025(15) -0.0183(16) 0.0009(15) C14 0.053(2) 0.063(2) 0.054(2) -0.0013(19) -0.0299(19) 0.0039(18) C15 0.066(3) 0.090(3) 0.044(2) -0.005(2) -0.029(2) -0.005(2) C16 0.062(2) 0.071(3) 0.047(2) -0.0146(19) -0.0144(19) -0.004(2) C17 0.048(2) 0.044(2) 0.046(2) -0.0108(16) -0.0153(17) 0.0002(16) C18 0.0403(18) 0.0379(18) 0.0387(18) -0.0036(14) -0.0150(15) -0.0003(14) C19 0.0378(18) 0.0362(18) 0.0421(19) -0.0060(15) -0.0174(15) 0.0074(14) C20 0.0440(19) 0.0381(19) 0.044(2) 0.0001(15) -0.0170(16) 0.0050(15) N21 0.064(2) 0.0476(18) 0.0417(17) -0.0045(14) -0.0222(15) 0.0030(15) C21 0.112(4) 0.069(3) 0.054(2) -0.009(2) -0.043(3) 0.000(3) C22 0.054(2) 0.0357(19) 0.044(2) -0.0009(15) -0.0088(17) 0.0094(16) C23 0.075(3) 0.064(3) 0.049(2) 0.000(2) 0.001(2) 0.014(2) C24 0.051(3) 0.083(3) 0.089(4) 0.013(3) 0.009(3) 0.000(2) C25 0.043(2) 0.081(3) 0.104(4) 0.015(3) -0.017(3) -0.007(2) C26 0.046(2) 0.059(3) 0.074(3) 0.000(2) -0.021(2) 0.0012(19) C27 0.0408(19) 0.0382(19) 0.049(2) -0.0033(16) -0.0134(16) 0.0083(15) C28 0.0420(18) 0.0309(17) 0.0431(19) 0.0022(14) -0.0156(15) 0.0029(14) C29 0.045(2) 0.043(2) 0.043(2) -0.0087(16) -0.0117(16) 0.0078(16) N30 0.0414(16) 0.0422(17) 0.0537(18) -0.0048(14) -0.0080(14) -0.0003(13) C30 0.050(2) 0.065(3) 0.084(3) -0.016(2) -0.013(2) -0.008(2) C31 0.051(2) 0.0368(19) 0.050(2) -0.0009(16) -0.0135(18) 0.0066(16) C32 0.051(2) 0.069(3) 0.051(2) 0.006(2) -0.0031(19) 0.0099(19) C33 0.078(3) 0.100(4) 0.047(2) 0.002(2) -0.020(2) 0.010(3) C34 0.084(3) 0.078(3) 0.057(3) -0.013(2) -0.035(2) 0.016(3) C35 0.056(2) 0.061(2) 0.052(2) -0.0022(19) -0.0218(19) 0.0064(19) C36 0.047(2) 0.0362(19) 0.045(2) 0.0024(15) -0.0169(16) 0.0071(15) _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 C9 1.374(4) . ? C1 N2 1.399(4) . ? C1 C28 1.466(4) . ? N2 C3 1.374(4) . ? N2 C2 1.460(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.398(4) . ? C3 C8 1.412(4) . ? C4 C5 1.378(5) . ? C4 H4 0.9300 . ? C5 C6 1.403(5) . ? C5 H5 0.9300 . ? C6 C7 1.376(4) . ? C6 H6 0.9300 . ? C7 C8 1.399(4) . ? C7 H7 0.9300 . ? C8 C9 1.440(4) . ? C9 C10 1.476(4) . ? C10 C11 1.386(4) . ? C10 C18 1.429(4) . ? C11 N12 1.399(4) . ? C11 C19 1.458(4) . ? N12 C13 1.376(4) . ? N12 C12 1.463(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.390(5) . ? C13 C18 1.417(4) . ? C14 C15 1.380(5) . ? C14 H14 0.9300 . ? C15 C16 1.399(5) . ? C15 H15 0.9300 . ? C16 C17 1.374(5) . ? C16 H16 0.9300 . ? C17 C18 1.402(4) . ? C17 H17 0.9300 . ? C19 C20 1.352(4) . ? C19 C27 1.448(4) . ? C20 N21 1.371(4) . ? C20 H20 0.9300 . ? N21 C22 1.373(4) . ? N21 C21 1.449(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.400(5) . ? C22 C27 1.404(5) . ? C23 C24 1.360(6) . ? C23 H23 0.9300 . ? C24 C25 1.395(7) . ? C24 H24 0.9300 . ? C25 C26 1.377(6) . ? C25 H25 0.9300 . ? C26 C27 1.401(5) . ? C26 H26 0.9300 . ? C28 C29 1.347(4) . ? C28 C36 1.440(5) . ? C29 N30 1.367(4) . ? C29 H29 0.9300 . ? N30 C31 1.367(4) . ? N30 C30 1.458(4) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C32 1.398(5) . ? C31 C36 1.415(5) . ? C32 C33 1.368(6) . ? C32 H32 0.9300 . ? C33 C34 1.388(6) . ? C33 H33 0.9300 . ? C34 C35 1.387(5) . ? C34 H34 0.9300 . ? C35 C36 1.389(5) . ? C35 H35 0.9300 . ? 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 C9 C1 N2 109.5(3) . . ? C9 C1 C28 129.9(3) . . ? N2 C1 C28 120.4(3) . . ? C3 N2 C1 108.4(2) . . ? C3 N2 C2 123.8(3) . . ? C1 N2 C2 125.8(3) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 129.5(3) . . ? N2 C3 C8 108.2(3) . . ? C4 C3 C8 122.2(3) . . ? C5 C4 C3 117.5(3) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 121.1(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C3 118.5(3) . . ? C7 C8 C9 134.4(3) . . ? C3 C8 C9 107.0(3) . . ? C1 C9 C8 106.8(3) . . ? C1 C9 C10 128.3(3) . . ? C8 C9 C10 124.9(3) . . ? C11 C10 C18 107.2(3) . . ? C11 C10 C9 128.2(3) . . ? C18 C10 C9 124.6(3) . . ? C10 C11 N12 108.7(3) . . ? C10 C11 C19 130.3(3) . . ? N12 C11 C19 120.8(3) . . ? C13 N12 C11 109.1(2) . . ? C13 N12 C12 123.3(3) . . ? C11 N12 C12 126.0(3) . . ? N12 C12 H12A 109.5 . . ? N12 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N12 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N12 C13 C14 130.2(3) . . ? N12 C13 C18 107.8(3) . . ? C14 C13 C18 122.1(3) . . ? C15 C14 C13 117.7(3) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 121.3(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 119.3(3) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C13 118.4(3) . . ? C17 C18 C10 134.1(3) . . ? C13 C18 C10 107.3(3) . . ? C20 C19 C27 105.8(3) . . ? C20 C19 C11 127.9(3) . . ? C27 C19 C11 126.2(3) . . ? C19 C20 N21 111.4(3) . . ? C19 C20 H20 124.3 . . ? N21 C20 H20 124.3 . . ? C20 N21 C22 107.9(3) . . ? C20 N21 C21 126.4(3) . . ? C22 N21 C21 125.7(3) . . ? N21 C21 H21A 109.5 . . ? N21 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N21 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N21 C22 C23 129.6(4) . . ? N21 C22 C27 108.2(3) . . ? C23 C22 C27 122.1(4) . . ? C24 C23 C22 117.5(4) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? C23 C24 C25 121.8(4) . . ? C23 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? C26 C25 C24 120.8(4) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 119.3(4) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C26 C27 C22 118.5(3) . . ? C26 C27 C19 134.9(3) . . ? C22 C27 C19 106.7(3) . . ? C29 C28 C36 106.5(3) . . ? C29 C28 C1 127.7(3) . . ? C36 C28 C1 125.7(3) . . ? C28 C29 N30 111.0(3) . . ? C28 C29 H29 124.5 . . ? N30 C29 H29 124.5 . . ? C29 N30 C31 108.4(3) . . ? C29 N30 C30 126.2(3) . . ? C31 N30 C30 125.3(3) . . ? N30 C30 H30A 109.5 . . ? N30 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N30 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N30 C31 C32 130.9(4) . . ? N30 C31 C36 107.9(3) . . ? C32 C31 C36 121.3(4) . . ? C33 C32 C31 118.3(4) . . ? C33 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? C32 C33 C34 121.1(4) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C35 C34 C33 121.1(4) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C34 C35 C36 119.2(4) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C35 C36 C31 118.9(3) . . ? C35 C36 C28 135.0(3) . . ? C31 C36 C28 106.2(3) . . ? 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 C9 C1 N2 C3 0.8(4) . . . . ? C28 C1 N2 C3 176.8(3) . . . . ? C9 C1 N2 C2 165.3(3) . . . . ? C28 C1 N2 C2 -18.7(5) . . . . ? C1 N2 C3 C4 -178.6(3) . . . . ? C2 N2 C3 C4 16.6(6) . . . . ? C1 N2 C3 C8 -0.3(4) . . . . ? C2 N2 C3 C8 -165.2(3) . . . . ? N2 C3 C4 C5 176.9(4) . . . . ? C8 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C3 -0.2(5) . . . . ? C6 C7 C8 C9 -176.6(4) . . . . ? N2 C3 C8 C7 -177.5(3) . . . . ? C4 C3 C8 C7 0.9(5) . . . . ? N2 C3 C8 C9 -0.2(4) . . . . ? C4 C3 C8 C9 178.2(3) . . . . ? N2 C1 C9 C8 -0.9(4) . . . . ? C28 C1 C9 C8 -176.4(3) . . . . ? N2 C1 C9 C10 178.8(3) . . . . ? C28 C1 C9 C10 3.3(6) . . . . ? C7 C8 C9 C1 177.4(4) . . . . ? C3 C8 C9 C1 0.7(4) . . . . ? C7 C8 C9 C10 -2.3(6) . . . . ? C3 C8 C9 C10 -179.0(3) . . . . ? C1 C9 C10 C11 -53.5(5) . . . . ? C8 C9 C10 C11 126.2(4) . . . . ? C1 C9 C10 C18 129.1(4) . . . . ? C8 C9 C10 C18 -51.3(5) . . . . ? C18 C10 C11 N12 0.1(3) . . . . ? C9 C10 C11 N12 -177.7(3) . . . . ? C18 C10 C11 C19 -174.7(3) . . . . ? C9 C10 C11 C19 7.5(5) . . . . ? C10 C11 N12 C13 0.0(4) . . . . ? C19 C11 N12 C13 175.4(3) . . . . ? C10 C11 N12 C12 165.7(3) . . . . ? C19 C11 N12 C12 -18.9(5) . . . . ? C11 N12 C13 C14 -179.4(3) . . . . ? C12 N12 C13 C14 14.4(6) . . . . ? C11 N12 C13 C18 -0.2(4) . . . . ? C12 N12 C13 C18 -166.3(3) . . . . ? N12 C13 C14 C15 176.5(3) . . . . ? C18 C13 C14 C15 -2.6(5) . . . . ? C13 C14 C15 C16 0.4(6) . . . . ? C14 C15 C16 C17 1.2(6) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C16 C17 C18 C13 -1.6(5) . . . . ? C16 C17 C18 C10 -176.6(4) . . . . ? N12 C13 C18 C17 -176.1(3) . . . . ? C14 C13 C18 C17 3.3(5) . . . . ? N12 C13 C18 C10 0.2(4) . . . . ? C14 C13 C18 C10 179.5(3) . . . . ? C11 C10 C18 C17 175.2(4) . . . . ? C9 C10 C18 C17 -6.8(6) . . . . ? C11 C10 C18 C13 -0.2(3) . . . . ? C9 C10 C18 C13 177.7(3) . . . . ? C10 C11 C19 C20 -50.8(5) . . . . ? N12 C11 C19 C20 135.0(3) . . . . ? C10 C11 C19 C27 124.4(4) . . . . ? N12 C11 C19 C27 -49.8(5) . . . . ? C27 C19 C20 N21 0.8(4) . . . . ? C11 C19 C20 N21 176.9(3) . . . . ? C19 C20 N21 C22 -0.5(4) . . . . ? C19 C20 N21 C21 178.6(3) . . . . ? C20 N21 C22 C23 179.2(3) . . . . ? C21 N21 C22 C23 0.1(6) . . . . ? C20 N21 C22 C27 -0.1(3) . . . . ? C21 N21 C22 C27 -179.2(3) . . . . ? N21 C22 C23 C24 -179.7(4) . . . . ? C27 C22 C23 C24 -0.5(5) . . . . ? C22 C23 C24 C25 -0.4(7) . . . . ? C23 C24 C25 C26 0.5(7) . . . . ? C24 C25 C26 C27 0.3(6) . . . . ? C25 C26 C27 C22 -1.2(5) . . . . ? C25 C26 C27 C19 178.9(4) . . . . ? N21 C22 C27 C26 -179.4(3) . . . . ? C23 C22 C27 C26 1.3(5) . . . . ? N21 C22 C27 C19 0.6(3) . . . . ? C23 C22 C27 C19 -178.8(3) . . . . ? C20 C19 C27 C26 179.1(4) . . . . ? C11 C19 C27 C26 3.0(6) . . . . ? C20 C19 C27 C22 -0.9(3) . . . . ? C11 C19 C27 C22 -177.0(3) . . . . ? C9 C1 C28 C29 -50.7(5) . . . . ? N2 C1 C28 C29 134.2(3) . . . . ? C9 C1 C28 C36 125.2(4) . . . . ? N2 C1 C28 C36 -49.9(5) . . . . ? C36 C28 C29 N30 1.4(4) . . . . ? C1 C28 C29 N30 177.9(3) . . . . ? C28 C29 N30 C31 -0.5(4) . . . . ? C28 C29 N30 C30 -177.3(3) . . . . ? C29 N30 C31 C32 178.4(3) . . . . ? C30 N30 C31 C32 -4.8(6) . . . . ? C29 N30 C31 C36 -0.6(3) . . . . ? C30 N30 C31 C36 176.2(3) . . . . ? N30 C31 C32 C33 178.9(4) . . . . ? C36 C31 C32 C33 -2.2(5) . . . . ? C31 C32 C33 C34 0.0(6) . . . . ? C32 C33 C34 C35 1.5(7) . . . . ? C33 C34 C35 C36 -0.8(6) . . . . ? C34 C35 C36 C31 -1.4(5) . . . . ? C34 C35 C36 C28 179.5(3) . . . . ? N30 C31 C36 C35 -178.0(3) . . . . ? C32 C31 C36 C35 2.9(5) . . . . ? N30 C31 C36 C28 1.4(3) . . . . ? C32 C31 C36 C28 -177.7(3) . . . . ? C29 C28 C36 C35 177.5(4) . . . . ? C1 C28 C36 C35 1.0(6) . . . . ? C29 C28 C36 C31 -1.7(3) . . . . ? C1 C28 C36 C31 -178.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 65.02 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.192 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.046 #======================================================================= # 1. SUBMISSION DETAILS _publ_requested_journal 'J. Chem. Soc. Perkin Translation 1' _publ_requested_coeditor_name ? _publ_contact_author ; Prof. Peter Luger Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; _publ_contact_author_phone '0049-030-83853411' _publ_contact_author_fax '0049-030-83853464' _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_letter ; This material is intended solely for deposition ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of Novel 1-Methylindole Trimer and Tetramer Under Friedel-Crafts Reaction Conditions and Determination of their Structures by X-Ray Crystallography. ; loop_ _publ_author_name _publ_author_address 'Luger, Peter' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Weber, Manuela' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Mahato, Shashi B.' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; 'Garai, Subhadra' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; #======================================================================= # 4. TEXT _publ_section_abstract ; ... and following paragraphs: see the published paper. ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #end of data