# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2002 data_n177 _database_code_CSD 188632 data_global #------------------ AUDIT DETAILS-------------------------------------------# _audit_creation_date 2002-06-26 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? _journal_coden_Cambridge ? loop_ _publ_author_name 'Marija Sindler' 'Nikola Basaric' 'Axel G. Griesbeck' 'Biserka Kojic-Prodic' 'Zeljko Marinic' 'Aleksandar Visnjevac' _publ_contact_author_name 'Prof Marija Sindler' _publ_contact_author_address ; Department of Organic Chemistry University of Zagreb Marulicev trg 19 Zagreb 10000 CROATIA ; _publ_contact_author_email MARIJA.SINDLER@PIERRE.FKIT.HR _publ_requested_journal 'Photochemical & Photobiological Sciences' _publ_section_title ; Photochemical transformations of 2,2'-(1,2-phenylenedivinylene)dipyrroles ; _publ_section_references ; Allen, F.H., Kennard, O. & Taylor, R. (1983). Acc. Chem. Res. 16, 146-153. Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350. Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Beurskens, P.T., Beurskens, G., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft, The Netherlands. Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4 Diffractometer Data. University of Marburg, Germany. Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA. Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst, A24, 351-359 Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G., & Taylor, R. (1992). International Tables for Crystallography, Volume C. Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3, edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189. Oxford University Press. Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Spek, A.L. (1990). Acta Cryst. A46, C34 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; Figure 1. View of (I) (50% probability displacement ellipsoids) ; _publ_section_table_legends ; Table 1. Fractional atomic coordinates and equivalent isotropic displacement parameters (\%A^2^) Table 2. Selected geometric parameters (\%A ,\% ) ; _audit_creation_date 2002-06-26T14:37:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_name_systematic ; E-2-{[2-(5-methyl-2-pyrrolyl)indan-1-yliden]methinyl}-5-methylpyrrole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2' _chemical_formula_sum 'C40 H40 N4' _chemical_formula_weight 576.76 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.969(6) _cell_length_b 12.00(2) _cell_length_c 16.26(5) _cell_angle_alpha 96.4(2) _cell_angle_beta 93.3(1) _cell_angle_gamma 101.3(1) _cell_volume 1700(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 10.02 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_process_details ; North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. ; _exptl_absorpt_correction_T_min 0.8518 _exptl_absorpt_correction_T_max 0.9604 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\q/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -2 0 1 1 1 0 1 -3 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_reflns_number 7293 _diffrn_reflns_av_R_equivalents 0.1284 _diffrn_reflns_av_sigmaI/netI 0.2677 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.32 _diffrn_reflns_theta_full 26.32 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.989 _reflns_number_total 6835 _reflns_number_gt 1344 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD-4 Express,(Enraf Nonius, 1992)' _computing_cell_refinement 'SET4 and CELDIM in CAD-4Software (Enraf-Nonius, 1992)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SIR97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6835 _refine_ls_number_parameters 557 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1771 _refine_ls_goodness_of_fit_ref 0.831 _refine_ls_restrained_S_all 0.831 _refine_ls_shift/su_max 0.03 _refine_diff_density_max 0.178 _refine_diff_density_min -0.164 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' 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_group _atom_site_disorder_assembly N12 N 1.0900(6) -0.1934(5) 0.0650(3) 0.0552(15) Uani 1 d . . . N18 N 0.7272(5) -0.2377(5) 0.1192(4) 0.0589(15) Uani 1 d . . . N40 N 0.2547(6) -0.3008(5) 0.3075(4) 0.0600(15) Uani 1 d . . . C13 C 1.1984(9) -0.2556(6) 0.0502(4) 0.0644(18) Uani 1 d . . . C9 C 0.9228(7) 0.0007(5) 0.1348(3) 0.0521(16) Uani 1 d . . . C10 C 1.0581(8) -0.0217(6) 0.1613(4) 0.0580(18) Uani 1 d . . . C20 C 0.6718(8) -0.3696(7) 0.0111(6) 0.079(2) Uani 1 d . . . C17 C 0.7591(6) -0.1817(6) 0.0520(5) 0.0552(17) Uani 1 d . . . C19 C 0.6734(7) -0.3520(6) 0.0959(5) 0.0655(19) Uani 1 d . . . C26 C 0.3791(8) 0.0242(6) 0.3828(4) 0.0627(18) Uani 1 d . . . C15 C 1.2851(7) -0.1161(6) 0.1552(5) 0.064(2) Uani 1 d . . . C11 C 1.1380(7) -0.1063(6) 0.1300(4) 0.0561(17) Uani 1 d . . . C24 C 0.1798(10) 0.0985(9) 0.4507(5) 0.096(3) Uani 1 d . . . C29 C 0.2381(9) -0.0994(7) 0.4665(5) 0.077(2) Uani 1 d . . . C31 C 0.4512(8) -0.0744(5) 0.3809(4) 0.0573(17) Uani 1 d . . . C8 C 0.8131(8) -0.0543(6) 0.0602(4) 0.062(2) Uani 1 d . . . C7 C 0.6821(8) 0.0115(7) 0.0616(6) 0.076(2) Uani 1 d . . . C25 C 0.2580(9) 0.0124(7) 0.4333(4) 0.072(2) Uani 1 d . . . C30 C 0.3648(8) -0.1590(6) 0.4337(4) 0.0669(19) Uani 1 d . . . C14 C 1.3202(9) -0.2077(7) 0.1055(5) 0.075(2) Uani 1 d . . . C42 C 0.2141(10) -0.4636(7) 0.3560(7) 0.109(3) Uani 1 d . . . C41 C 0.1999(8) -0.4159(7) 0.2857(6) 0.082(2) Uani 1 d . . . C39 C 0.3038(7) -0.2762(6) 0.3905(4) 0.0611(18) Uani 1 d . . . N34 N 0.6402(8) -0.2688(6) 0.3719(4) 0.0740(19) Uani 1 d . . . C22 C 0.6317(13) -0.4332(8) 0.1574(6) 0.093(3) Uani 1 d . . . C32 C 0.5807(9) -0.0799(6) 0.3458(4) 0.061(2) Uani 1 d . . . C33 C 0.6757(9) -0.1619(6) 0.3450(4) 0.0666(19) Uani 1 d . . . C5 C 0.7247(9) 0.1023(6) 0.1325(5) 0.0704(19) Uani 1 d . . . C2 C 0.8387(13) 0.2598(8) 0.2680(7) 0.109(3) Uani 1 d . . . C28 C 0.3385(13) 0.2113(8) 0.3627(6) 0.099(3) Uani 1 d . . . C27 C 0.4200(10) 0.1242(8) 0.3481(5) 0.082(2) Uani 1 d . . . C37 C 0.8238(10) -0.1542(9) 0.3239(5) 0.083(3) Uani 1 d . . . C35 C 0.7572(11) -0.3233(8) 0.3693(4) 0.082(2) Uani 1 d . . . C6 C 0.6483(10) 0.1890(9) 0.1607(7) 0.091(3) Uani 1 d . . . C4 C 0.8604(8) 0.0950(6) 0.1750(4) 0.0619(18) Uani 1 d . . . C36 C 0.8733(10) -0.2536(9) 0.3393(5) 0.085(3) Uani 1 d . . . C43 C 0.2819(9) -0.3785(8) 0.4211(6) 0.097(3) Uani 1 d . . . C1 C 0.7047(14) 0.2655(9) 0.2262(7) 0.116(3) Uani 1 d . . . C21 C 0.7248(8) -0.2621(7) -0.0162(5) 0.073(2) Uani 1 d . . . C23 C 0.2205(13) 0.1968(10) 0.4143(6) 0.104(3) Uani 1 d . . . C3 C 0.9180(10) 0.1722(7) 0.2445(5) 0.085(2) Uani 1 d . . . C38 C 0.7451(17) -0.4397(10) 0.3966(8) 0.134(4) Uani 1 d . . . C44 C 0.134(2) -0.4676(10) 0.1991(7) 0.128(4) Uani 1 d . . . C16 C 1.1673(14) -0.3576(8) -0.0127(7) 0.095(3) Uani 1 d . . . H1 H 0.994(5) -0.207(4) 0.046(3) 0.045(18) Uiso 1 d . . . H2 H 0.737(4) -0.207(3) 0.169(2) 0.010(14) Uiso 1 d . . . H3 H 0.266(6) -0.251(5) 0.270(3) 0.08(2) Uiso 1 d . . . H4 H 1.099(5) 0.025(4) 0.210(3) 0.06(2) Uiso 1 d . . . H5 H 0.629(6) -0.443(5) -0.029(3) 0.10(2) Uiso 1 d . . . H6 H 1.352(6) -0.059(4) 0.200(3) 0.08(2) Uiso 1 d . . . H7 H 0.093(8) 0.102(6) 0.497(5) 0.16(3) Uiso 1 d . . . H8 H 0.260(5) -0.086(4) 0.527(3) 0.053(18) Uiso 1 d . . . H9 H 0.136(7) -0.142(5) 0.453(3) 0.09(2) Uiso 1 d . . . H10 H 0.862(4) -0.044(3) 0.015(2) 0.021(14) Uiso 1 d . . . H11 H 0.659(5) 0.033(4) 0.009(3) 0.043(17) Uiso 1 d . . . H12 H 0.589(6) -0.043(4) 0.069(3) 0.066(19) Uiso 1 d . . . H13 H 0.437(6) -0.167(4) 0.480(3) 0.08(2) Uiso 1 d . . . H14 H 1.406(5) -0.240(4) 0.101(3) 0.046(17) Uiso 1 d . . . H15 H 0.192(6) -0.545(5) 0.351(3) 0.08(2) Uiso 1 d . . . H16 H 0.554(6) -0.295(4) 0.385(3) 0.05(2) Uiso 1 d . . . H17 H 0.603(7) -0.507(5) 0.133(3) 0.09(2) Uiso 1 d . . . H18 H 0.734(9) -0.442(6) 0.197(5) 0.19(4) Uiso 1 d . . . H19 H 0.575(7) -0.403(5) 0.199(4) 0.11(3) Uiso 1 d . . . H20 H 0.621(6) -0.022(4) 0.317(3) 0.08(2) Uiso 1 d . . . H21 H 0.883(7) 0.312(6) 0.319(4) 0.13(3) Uiso 1 d . . . H22 H 0.364(7) 0.280(6) 0.333(4) 0.14(3) Uiso 1 d . . . H23 H 0.502(5) 0.124(4) 0.310(3) 0.06(2) Uiso 1 d . . . H24 H 0.867(6) -0.094(4) 0.307(3) 0.05(2) Uiso 1 d . . . H25 H 0.568(6) 0.184(4) 0.122(3) 0.06(2) Uiso 1 d . . . H26 H 0.976(7) -0.262(5) 0.327(3) 0.10(2) Uiso 1 d . . . H29 H 0.627(6) 0.326(5) 0.249(4) 0.11(2) Uiso 1 d . . . H30 H 0.726(6) -0.244(5) -0.069(3) 0.09(2) Uiso 1 d . . . H31 H 0.157(6) 0.254(5) 0.428(3) 0.09(2) Uiso 1 d . . . H32 H 1.028(6) 0.172(5) 0.274(3) 0.10(2) Uiso 1 d . . . H33 H 0.813(7) -0.469(5) 0.374(4) 0.08(3) Uiso 1 d . . . H34 H 0.765(8) -0.425(6) 0.458(4) 0.13(3) Uiso 1 d . . . H35 H 0.670(12) -0.492(9) 0.347(7) 0.26(6) Uiso 1 d . . . H36 H 0.099(11) -0.555(9) 0.214(6) 0.25(5) Uiso 1 d . . . H37 H 0.089(15) -0.422(10) 0.172(8) 0.26(8) Uiso 1 d . . . H38 H 0.206(9) -0.450(7) 0.160(6) 0.16(4) Uiso 1 d . . . H39 H 1.257(9) -0.399(7) -0.020(5) 0.20(5) Uiso 1 d . . . H40 H 1.060(14) -0.397(9) -0.032(9) 0.33(8) Uiso 1 d . . . H41 H 1.147(5) -0.346(4) -0.060(2) 0.012(16) Uiso 1 d . . . H42 H 0.300(5) -0.375(4) 0.482(3) 0.051(17) Uiso 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 N12 0.038(4) 0.063(4) 0.064(4) 0.015(3) 0.004(3) 0.006(4) N18 0.056(4) 0.062(4) 0.052(4) 0.001(4) -0.002(3) 0.002(3) N40 0.061(4) 0.056(4) 0.059(4) 0.012(4) 0.007(3) -0.001(3) C13 0.059(5) 0.059(5) 0.080(6) 0.018(4) 0.014(4) 0.015(5) C9 0.039(4) 0.066(4) 0.053(4) 0.015(3) 0.005(3) 0.007(4) C10 0.049(5) 0.058(5) 0.062(5) 0.001(4) 0.009(4) 0.001(4) C20 0.078(5) 0.064(6) 0.082(6) -0.013(5) -0.014(5) 0.003(4) C17 0.038(4) 0.069(5) 0.059(5) 0.013(4) -0.006(3) 0.011(4) C19 0.052(4) 0.066(6) 0.073(6) 0.010(5) -0.005(4) 0.002(4) C26 0.064(5) 0.066(5) 0.054(5) 0.004(4) -0.006(4) 0.010(4) C15 0.049(5) 0.064(5) 0.079(6) 0.026(4) -0.005(4) 0.005(4) C11 0.049(5) 0.060(5) 0.057(5) 0.019(4) -0.008(4) 0.002(4) C24 0.101(7) 0.110(8) 0.079(7) -0.013(6) -0.005(5) 0.044(7) C29 0.060(6) 0.090(7) 0.067(6) -0.008(5) -0.001(5) -0.005(5) C31 0.057(5) 0.057(4) 0.049(4) 0.009(3) -0.001(4) -0.009(4) C8 0.054(5) 0.077(6) 0.053(5) 0.026(4) 0.005(4) -0.001(4) C7 0.044(5) 0.088(7) 0.101(7) 0.040(6) 0.000(5) 0.013(5) C25 0.074(6) 0.076(6) 0.058(5) -0.010(4) -0.013(4) 0.012(5) C30 0.066(5) 0.067(5) 0.059(5) 0.006(4) -0.007(4) -0.005(4) C14 0.055(6) 0.074(6) 0.107(7) 0.034(5) 0.008(5) 0.026(5) C42 0.135(8) 0.047(6) 0.134(9) 0.017(6) 0.017(6) -0.015(5) C41 0.079(5) 0.060(6) 0.102(7) 0.010(6) 0.019(5) 0.000(4) C39 0.062(5) 0.062(5) 0.058(5) 0.010(4) 0.003(4) 0.007(4) N34 0.048(5) 0.087(5) 0.086(5) 0.014(4) 0.000(4) 0.012(5) C22 0.124(8) 0.051(6) 0.098(7) 0.014(6) 0.008(7) 0.002(6) C32 0.073(6) 0.060(5) 0.046(4) 0.015(4) -0.002(4) -0.001(5) C33 0.057(5) 0.071(6) 0.062(5) 0.010(4) 0.001(4) -0.011(5) C5 0.073(6) 0.061(5) 0.082(6) 0.025(4) 0.027(5) 0.009(5) C2 0.110(8) 0.078(7) 0.130(10) -0.013(6) 0.026(7) 0.006(7) C28 0.124(8) 0.087(7) 0.092(7) 0.019(6) -0.011(6) 0.036(7) C27 0.091(6) 0.088(6) 0.066(6) 0.017(5) 0.001(5) 0.016(6) C37 0.066(7) 0.107(8) 0.072(6) 0.018(5) 0.007(5) 0.001(6) C35 0.074(7) 0.095(7) 0.077(6) 0.001(5) -0.011(5) 0.027(6) C6 0.083(7) 0.095(7) 0.111(9) 0.048(6) 0.027(7) 0.031(7) C4 0.052(5) 0.067(5) 0.067(5) 0.020(4) 0.007(4) 0.006(4) C36 0.052(6) 0.126(8) 0.075(6) -0.012(5) -0.001(5) 0.031(6) C43 0.115(7) 0.095(7) 0.081(7) 0.034(6) -0.008(5) 0.009(5) C1 0.123(10) 0.100(8) 0.134(10) 0.017(7) 0.050(8) 0.031(8) C21 0.071(5) 0.089(7) 0.055(6) 0.002(5) -0.012(4) 0.014(5) C23 0.125(9) 0.118(9) 0.082(7) -0.011(6) -0.011(6) 0.073(8) C3 0.084(6) 0.084(6) 0.083(6) -0.006(5) 0.008(5) 0.017(5) C38 0.191(12) 0.111(9) 0.121(10) -0.004(8) 0.000(10) 0.095(9) C44 0.202(12) 0.075(7) 0.077(7) 0.003(6) 0.018(8) -0.040(8) C16 0.120(9) 0.075(7) 0.093(8) 0.004(6) 0.021(7) 0.024(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N12 C11 1.3858 . . yes N12 C13 1.3530 . . yes N18 C17 1.3599 . . yes N18 C19 1.3652 . . yes N12 H1 0.8739 . . no N18 H2 0.8470 . . no N34 C35 1.3420 . . yes N34 C33 1.3846 . . yes N40 C39 1.3756 . . yes N40 C41 1.3709 . . yes N34 H16 0.8221 . . no N40 H3 0.8947 . . no C1 C6 1.3310 . . no C1 C2 1.3638 . . no C2 C3 1.4110 . . no C3 C4 1.3834 . . no C4 C5 1.3875 . . no C4 C9 1.4644 . . no C5 C6 1.4035 . . no C5 C7 1.4728 . . no C7 C8 1.5374 . . no C8 C9 1.5182 . . no C8 C17 1.4991 . . no C9 C10 1.3502 . . no C10 C11 1.4191 . . no C11 C15 1.3899 . . no C13 C16 1.4755 . . no C13 C14 1.3630 . . no C14 C15 1.3886 . . no C17 C21 1.3641 . . no C19 C22 1.4850 . . no C19 C20 1.3701 . . no C20 C21 1.4141 . . no C1 H29 1.1527 . . no C2 H21 0.9925 . . no C3 H32 1.0672 . . no C6 H25 0.9148 . . no C7 H11 0.9464 . . no C7 H12 0.9804 . . no C8 H10 0.8801 . . no C10 H4 0.9255 . . no C14 H14 0.9268 . . no C15 H6 1.0215 . . no C16 H40 1.0033 . . no C16 H39 1.0315 . . no C16 H41 0.8182 . . no C20 H5 1.0334 . . no C21 H30 0.9094 . . no C22 H19 0.9538 . . no C22 H18 1.1161 . . no C22 H17 0.9081 . . no C23 C28 1.3845 . . no C23 C24 1.3734 . . no C24 C25 1.3713 . . no C25 C26 1.3945 . . no C25 C29 1.4835 . . no C26 C27 1.3763 . . no C26 C31 1.4541 . . no C27 C28 1.3951 . . no C29 C30 1.5467 . . no C30 C39 1.4859 . . no C30 C31 1.5256 . . no C31 C32 1.3331 . . no C32 C33 1.4218 . . no C33 C37 1.3798 . . no C35 C38 1.4971 . . no C35 C36 1.3527 . . no C36 C37 1.3948 . . no C39 C43 1.3580 . . no C41 C42 1.3437 . . no C41 C44 1.5103 . . no C42 C43 1.4056 . . no C23 H31 0.9857 . . no C24 H7 1.1153 . . no C27 H23 0.9865 . . no C28 H22 0.9930 . . no C29 H8 0.9735 . . no C29 H9 0.9596 . . no C30 H13 0.9866 . . no C32 H20 0.9053 . . no C36 H26 0.9716 . . no C37 H24 0.8362 . . no C38 H33 0.8454 . . no C38 H34 0.9928 . . no C38 H35 1.0710 . . no C42 H15 0.9516 . . no C43 H42 0.9878 . . no C44 H36 1.0907 . . no C44 H37 0.8795 . . no C44 H38 0.9417 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N12 C13 111.61 . . . yes C17 N18 C19 111.12 . . . yes C11 N12 H1 117.82 . . . no C13 N12 H1 129.72 . . . no C17 N18 H2 125.50 . . . no C19 N18 H2 123.37 . . . no C33 N34 C35 112.40 . . . yes C39 N40 C41 111.37 . . . yes C33 N34 H16 121.87 . . . no C35 N34 H16 125.60 . . . no C41 N40 H3 122.64 . . . no C39 N40 H3 125.60 . . . no C2 C1 C6 119.90 . . . no C1 C2 C3 121.24 . . . no C2 C3 C4 118.32 . . . no C3 C4 C9 129.60 . . . no C3 C4 C5 119.83 . . . no C5 C4 C9 110.56 . . . no C4 C5 C6 119.16 . . . no C4 C5 C7 111.31 . . . no C6 C5 C7 129.52 . . . no C1 C6 C5 121.47 . . . no C5 C7 C8 105.43 . . . no C9 C8 C17 116.94 . . . no C7 C8 C17 113.28 . . . no C7 C8 C9 105.83 . . . no C4 C9 C8 106.79 . . . no C8 C9 C10 130.44 . . . no C4 C9 C10 122.66 . . . no C9 C10 C11 130.83 . . . no N12 C11 C10 127.79 . . . yes C10 C11 C15 127.33 . . . no N12 C11 C15 104.81 . . . yes N12 C13 C14 106.44 . . . yes C14 C13 C16 132.84 . . . no N12 C13 C16 120.61 . . . yes C13 C14 C15 109.05 . . . no C11 C15 C14 108.09 . . . no C8 C17 C21 131.35 . . . no N18 C17 C21 106.74 . . . yes N18 C17 C8 121.83 . . . yes N18 C19 C22 122.09 . . . yes N18 C19 C20 106.65 . . . yes C20 C19 C22 131.25 . . . no C19 C20 C21 107.46 . . . no C17 C21 C20 108.03 . . . no C6 C1 H29 116.20 . . . no C2 C1 H29 123.37 . . . no C3 C2 H21 115.32 . . . no C1 C2 H21 123.24 . . . no C4 C3 H32 119.82 . . . no C2 C3 H32 121.28 . . . no C1 C6 H25 132.04 . . . no C5 C6 H25 106.02 . . . no C8 C7 H11 111.70 . . . no H11 C7 H12 101.81 . . . no C5 C7 H12 111.98 . . . no C5 C7 H11 118.20 . . . no C8 C7 H12 107.40 . . . no C17 C8 H10 102.89 . . . no C9 C8 H10 107.65 . . . no C7 C8 H10 110.07 . . . no C9 C10 H4 111.20 . . . no C11 C10 H4 117.84 . . . no C15 C14 H14 134.68 . . . no C13 C14 H14 116.24 . . . no C11 C15 H6 122.34 . . . no C14 C15 H6 129.44 . . . no H39 C16 H41 101.86 . . . no C13 C16 H39 115.01 . . . no H40 C16 H41 70.21 . . . no H39 C16 H40 121.26 . . . no C13 C16 H41 115.31 . . . no C13 C16 H40 120.76 . . . no C19 C20 H5 129.09 . . . no C21 C20 H5 123.03 . . . no C20 C21 H30 128.30 . . . no C17 C21 H30 123.25 . . . no C19 C22 H19 111.98 . . . no H17 C22 H18 99.10 . . . no H17 C22 H19 120.99 . . . no H18 C22 H19 99.74 . . . no C19 C22 H18 111.75 . . . no C19 C22 H17 111.54 . . . no C24 C23 C28 121.97 . . . no C23 C24 C25 118.05 . . . no C24 C25 C26 121.80 . . . no C26 C25 C29 110.12 . . . no C24 C25 C29 127.97 . . . no C25 C26 C31 110.72 . . . no C27 C26 C31 129.86 . . . no C25 C26 C27 119.24 . . . no C26 C27 C28 119.83 . . . no C23 C28 C27 119.06 . . . no C25 C29 C30 106.81 . . . no C29 C30 C31 103.93 . . . no C29 C30 C39 112.67 . . . no C31 C30 C39 115.53 . . . no C26 C31 C30 108.38 . . . no C30 C31 C32 127.66 . . . no C26 C31 C32 123.55 . . . no C31 C32 C33 131.79 . . . no N34 C33 C32 126.16 . . . yes N34 C33 C37 103.54 . . . yes C32 C33 C37 130.17 . . . no C36 C35 C38 131.50 . . . no N34 C35 C36 106.89 . . . yes N34 C35 C38 121.62 . . . yes C35 C36 C37 107.90 . . . no C33 C37 C36 109.27 . . . no N40 C39 C30 124.41 . . . yes N40 C39 C43 105.87 . . . yes C30 C39 C43 129.71 . . . no N40 C41 C42 105.47 . . . yes C42 C41 C44 131.33 . . . no N40 C41 C44 123.16 . . . yes C41 C42 C43 109.61 . . . no C39 C43 C42 107.63 . . . no C24 C23 H31 113.94 . . . no C28 C23 H31 124.08 . . . no C23 C24 H7 114.71 . . . no C25 C24 H7 126.95 . . . no C26 C27 H23 114.52 . . . no C28 C27 H23 125.44 . . . no C23 C28 H22 122.58 . . . no C27 C28 H22 118.29 . . . no C25 C29 H8 109.03 . . . no C25 C29 H9 110.26 . . . no C30 C29 H8 104.93 . . . no C30 C29 H9 115.49 . . . no H8 C29 H9 110.04 . . . no C29 C30 H13 110.64 . . . no C31 C30 H13 107.14 . . . no C39 C30 H13 106.83 . . . no C31 C32 H20 118.40 . . . no C33 C32 H20 109.81 . . . no C35 C36 H26 132.14 . . . no C37 C36 H26 119.96 . . . no C33 C37 H24 117.88 . . . no C36 C37 H24 132.82 . . . no C35 C38 H33 106.86 . . . no C35 C38 H34 104.43 . . . no C35 C38 H35 101.19 . . . no H33 C38 H34 112.60 . . . no H33 C38 H35 83.66 . . . no H34 C38 H35 143.53 . . . no C41 C42 H15 117.10 . . . no C43 C42 H15 132.61 . . . no C39 C43 H42 115.86 . . . no C42 C43 H42 135.54 . . . no C41 C44 H36 96.01 . . . no C41 C44 H37 113.95 . . . no C41 C44 H38 111.42 . . . no H36 C44 H37 133.85 . . . no H36 C44 H38 120.99 . . . no H37 C44 H38 80.88 . . . no 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 C13 N12 C11 C10 177.69 . . . . no C13 N12 C11 C15 0.65 . . . . no C11 N12 C13 C14 -0.86 . . . . no C11 N12 C13 C16 175.84 . . . . no C19 N18 C17 C8 177.13 . . . . no C19 N18 C17 C21 0.07 . . . . no C17 N18 C19 C20 0.35 . . . . no C17 N18 C19 C22 179.24 . . . . no C33 N34 C35 C36 -0.80 . . . . no C33 N34 C35 C38 179.23 . . . . no C35 N34 C33 C37 0.97 . . . . no C35 N34 C33 C32 -175.21 . . . . no C39 N40 C41 C42 0.37 . . . . no C39 N40 C41 C44 178.38 . . . . no C41 N40 C39 C43 1.08 . . . . no C41 N40 C39 C30 -177.99 . . . . no C6 C1 C2 C3 -1.57 . . . . no C2 C1 C6 C5 -0.71 . . . . no C1 C2 C3 C4 3.19 . . . . no C2 C3 C4 C9 176.60 . . . . no C2 C3 C4 C5 -2.54 . . . . no C3 C4 C9 C8 -179.11 . . . . no C3 C4 C5 C7 -179.06 . . . . no C9 C4 C5 C6 -178.90 . . . . no C3 C4 C5 C6 0.40 . . . . no C3 C4 C9 C10 -2.51 . . . . no C5 C4 C9 C8 0.10 . . . . no C9 C4 C5 C7 1.65 . . . . no C5 C4 C9 C10 176.70 . . . . no C7 C5 C6 C1 -179.36 . . . . no C4 C5 C7 C8 -2.65 . . . . no C4 C5 C6 C1 1.30 . . . . no C6 C5 C7 C8 177.97 . . . . no C5 C7 C8 C17 131.96 . . . . no C5 C7 C8 C9 2.57 . . . . no C9 C8 C17 N18 38.24 . . . . no C7 C8 C9 C10 -177.93 . . . . no C17 C8 C9 C4 -128.90 . . . . no C17 C8 C9 C10 54.86 . . . . no C7 C8 C17 N18 -85.25 . . . . no C9 C8 C17 C21 -145.53 . . . . no C7 C8 C17 C21 90.99 . . . . no C7 C8 C9 C4 -1.69 . . . . no C8 C9 C10 C11 -2.77 . . . . no C4 C9 C10 C11 -178.49 . . . . no C9 C10 C11 C15 172.25 . . . . no C9 C10 C11 N12 -4.15 . . . . no N12 C11 C15 C14 -0.18 . . . . no C10 C11 C15 C14 -177.24 . . . . no N12 C13 C14 C15 0.72 . . . . no C16 C13 C14 C15 -175.40 . . . . no C13 C14 C15 C11 -0.33 . . . . no C8 C17 C21 C20 -177.12 . . . . no N18 C17 C21 C20 -0.46 . . . . no C22 C19 C20 C21 -179.37 . . . . no N18 C19 C20 C21 -0.62 . . . . no C19 C20 C21 C17 0.68 . . . . no C28 C23 C24 C25 -1.25 . . . . no C24 C23 C28 C27 -0.93 . . . . no C23 C24 C25 C29 178.20 . . . . no C23 C24 C25 C26 2.26 . . . . no C24 C25 C26 C31 174.48 . . . . no C29 C25 C26 C27 -177.67 . . . . no C24 C25 C26 C27 -1.07 . . . . no C24 C25 C29 C30 -174.62 . . . . no C26 C25 C29 C30 1.70 . . . . no C29 C25 C26 C31 -2.11 . . . . no C25 C26 C31 C30 1.64 . . . . no C25 C26 C27 C28 -1.17 . . . . no C31 C26 C27 C28 -175.75 . . . . no C27 C26 C31 C32 3.37 . . . . no C25 C26 C31 C32 -171.58 . . . . no C27 C26 C31 C30 176.59 . . . . no C26 C27 C28 C23 2.14 . . . . no C25 C29 C30 C39 -126.45 . . . . no C25 C29 C30 C31 -0.66 . . . . no C29 C30 C31 C32 172.33 . . . . no C39 C30 C31 C26 123.42 . . . . no C39 C30 C31 C32 -63.71 . . . . no C29 C30 C39 N40 87.15 . . . . no C29 C30 C39 C43 -91.69 . . . . no C31 C30 C39 N40 -32.10 . . . . no C29 C30 C31 C26 -0.53 . . . . no C31 C30 C39 C43 149.06 . . . . no C26 C31 C32 C33 172.61 . . . . no C30 C31 C32 C33 0.74 . . . . no C31 C32 C33 N34 10.82 . . . . no C31 C32 C33 C37 -164.32 . . . . no N34 C33 C37 C36 -0.76 . . . . no C32 C33 C37 C36 175.21 . . . . no C38 C35 C36 C37 -179.75 . . . . no N34 C35 C36 C37 0.28 . . . . no C35 C36 C37 C33 0.32 . . . . no N40 C39 C43 C42 -2.04 . . . . no C30 C39 C43 C42 176.97 . . . . no C44 C41 C42 C43 -179.44 . . . . no N40 C41 C42 C43 -1.65 . . . . no C41 C42 C43 C39 2.38 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N12 C8 3.2553 . . no N12 C17 2.9952 . . no N12 C21 3.3697 . . no N18 C37 3.3787 . . no N34 C43 3.4018 . . no N34 C30 3.1794 . . no N34 C39 3.0338 . . no N18 H14 2.8762 . 1_455 no N18 H1 2.7161 . . no N34 H13 2.9431 . . no N40 H16 2.8839 . . no N40 H26 2.6638 . 1_455 no C1 C27 3.5994 . . no C6 C16 3.5845 . 2_775 no C8 N12 3.2553 . . no C11 C17 3.4661 . . no C16 C6 3.5845 . 2_775 no C17 C11 3.4661 . . no C17 N12 2.9952 . . no C21 N12 3.3697 . . no C22 C35 3.5832 . . no C24 C33 3.4423 . 2_676 no C27 C1 3.5994 . . no C30 N34 3.1794 . . no C33 C24 3.4423 . 2_676 no C33 C39 3.5027 . . no C35 C22 3.5832 . . no C37 N18 3.3787 . . no C39 C33 3.5027 . . no C39 N34 3.0338 . . no C43 N34 3.4018 . . no C1 H23 2.7632 . . no C3 H4 2.6614 . . no C6 H41 3.0433 . 2_775 no C6 H23 2.9366 . . no C8 H1 2.6794 . . no C9 H2 2.8420 . . no C9 H1 2.9419 . . no C10 H32 2.8574 . . no C11 H11 3.0784 . 2_775 no C13 H11 3.0118 . 2_775 no C13 H37 3.0384 . 1_655 no C14 H3 2.8358 . 1_655 no C14 H11 2.9393 . 2_775 no C14 H12 2.9336 . 1_655 no C15 H11 2.9851 . 2_775 no C15 H3 2.5983 . 1_655 no C17 H1 2.1962 . . no C19 H14 2.9743 . 1_455 no C20 H39 2.9880 . 2_765 no C21 H1 2.4983 . . no C22 H5 3.0640 . 2_665 no C23 H32 2.7399 . 1_455 no C26 H6 3.0036 . 1_455 no C26 H13 2.8720 . 2_676 no C27 H13 2.9570 . 2_676 no C27 H20 2.7853 . . no C27 H6 3.0194 . 1_455 no C28 H32 2.9941 . 1_455 no C29 H7 3.0551 . 2_576 no C30 H16 2.6760 . . no C31 H6 3.0549 . 1_455 no C31 H8 3.0999 . 2_676 no C31 H3 2.8115 . . no C31 H16 2.9802 . . no C32 H23 2.7899 . . no C32 H8 2.8142 . 2_676 no C33 H2 2.9535 . . no C35 H19 3.0871 . . no C35 H18 2.9773 . . no C36 H9 2.9090 . 1_655 no C36 H18 3.0721 . . no C36 H7 3.0232 . 2_676 no C37 H2 2.5611 . . no C37 H7 2.9384 . 2_676 no C39 H16 2.3081 . . no C41 H26 3.0376 . 1_455 no C43 H16 2.5799 . . no H1 C9 2.9419 . . no H1 N18 2.7161 . . no H1 C8 2.6794 . . no H1 H10 2.5546 . . no H1 C17 2.1962 . . no H1 C21 2.4983 . . no H2 C33 2.9535 . . no H2 C9 2.8420 . . no H2 C37 2.5611 . . no H2 H24 2.5668 . . no H3 C31 2.8115 . . no H3 C14 2.8358 . 1_455 no H3 C15 2.5983 . 1_455 no H4 C3 2.6614 . . no H4 H32 2.1696 . . no H5 C22 3.0640 . 2_665 no H5 H17 2.5248 . 2_665 no H5 H39 2.5085 . 2_765 no H6 C27 3.0194 . 1_655 no H6 C31 3.0549 . 1_655 no H6 C26 3.0036 . 1_655 no H7 C29 3.0551 . 2_576 no H7 C36 3.0232 . 2_676 no H7 C37 2.9384 . 2_676 no H7 H9 2.3639 . 2_576 no H8 C32 2.8142 . 2_676 no H8 C31 3.0999 . 2_676 no H9 H7 2.3639 . 2_576 no H9 C36 2.9090 . 1_455 no H9 H26 2.5523 . 1_455 no H10 H1 2.5546 . . no H10 H10 2.5954 . 2_775 no H11 C13 3.0118 . 2_775 no H11 C11 3.0784 . 2_775 no H11 H12 2.5237 . 2_675 no H11 C14 2.9393 . 2_775 no H11 C15 2.9851 . 2_775 no H12 C14 2.9336 . 1_455 no H12 H11 2.5237 . 2_675 no H13 N34 2.9431 . . no H13 H16 2.4870 . . no H13 C26 2.8720 . 2_676 no H13 C27 2.9570 . 2_676 no H13 H42 2.5655 . . no H14 C19 2.9743 . 1_655 no H14 N18 2.8762 . 1_655 no H15 H36 2.3201 . . no H16 N40 2.8839 . . no H16 C30 2.6760 . . no H16 C31 2.9802 . . no H16 C43 2.5799 . . no H16 H13 2.4870 . . no H16 C39 2.3081 . . no H17 H39 2.5610 . 2_765 no H17 H5 2.5248 . 2_665 no H18 C36 3.0721 . . no H18 C35 2.9773 . . no H19 C35 3.0871 . . no H20 H24 2.5228 . . no H20 C27 2.7853 . . no H20 H23 2.2405 . . no H23 C6 2.9366 . . no H23 C1 2.7632 . . no H23 C32 2.7899 . . no H23 H20 2.2405 . . no H24 H2 2.5668 . . no H24 H20 2.5228 . . no H26 H9 2.5523 . 1_655 no H26 N40 2.6638 . 1_655 no H26 C41 3.0376 . 1_655 no H29 H35 2.5055 . 1_565 no H31 H34 2.5663 . 2_676 no H32 C10 2.8574 . . no H32 C28 2.9941 . 1_655 no H32 H4 2.1696 . . no H32 C23 2.7399 . 1_655 no H34 H31 2.5663 . 2_676 no H35 H29 2.5055 . 1_545 no H36 H15 2.3201 . . no H37 C13 3.0384 . 1_455 no H39 H17 2.5610 . 2_765 no H39 C20 2.9880 . 2_765 no H39 H5 2.5085 . 2_765 no H41 C6 3.0433 . 2_775 no H42 H13 2.5655 . . no # End of Crystallographic Information File