# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/206 data_1 # 1. SUBMISSION DETAILS _publ_contact_autor ; Klaus M\"ullen MPI f\"ur Polymerforschung Postfach 3148 D-55021 Mainz Germany ; _publ_contact_author_phone '0049 6131 379150' _publ_contact_author_fax '0049 6131 379100' _publ_contact_author_email muellen@mpip-mainz.mpg.de _publ_requested_journal 'J. Mater. Chem.' _publ_requested_coeditor_name ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and crystal packing of large polycyclic aromatic hydrocarbons: Hexa-peri-hexabenzocoronene and Dibenzo[fg,ij]phenanthro[3,2,1,10,9-pqrst] pentaphene ; loop_ _publ_author_name _publ_author_address 'M\"ullen, Klaus' ; MPI f\"ur Polymerforschung Postfach 3148 D-55021 Mainz Germany ; 'K\"ubel, Christian' ; Max-Planck-Institut f\"ur Polymerforschung Postfach 3148 55021 Mainz Deutschland ; 'Eckhardt, Karin' ; Max-Planck-Institut f\"ur Polymerforschung Postfach 3148 55021 Mainz Deutschland ; 'Enkelmann, Volker' ; Max-Planck-Institut f\"ur Polymerforschung Postfach 3148 55021 Mainz Deutschland ; #============================================================================== data_kueb _audit_creation_method CRYSTALS _chemical_name_systematic ; Dibenzo[fg,ij]phenanthro[3,2,1,10,9-pqrst]pentaphene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H18' _chemical_formula_weight 450.54 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x, -y, z+1/2' '-x, -y, -z' '1/2+x, 1/2+y, z' '-x+1/2, 1/2+y, -z+1/2' '1/2+x, -y+1/2, z+1/2' '-x+1/2, -y+1/2, -z' _cell_length_a 45.381(1) _cell_length_b 5.1771(7) _cell_length_c 18.266(1) _cell_angle_alpha 90.00 _cell_angle_beta 106.293(6) _cell_angle_gamma 90.00 _cell_volume 4110.1 _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.38 _cell_measurement_theta_max 28.29 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method ? _exptl_absorpt_coefficient_mu 0.591 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method 'Theta-2theta scans' _diffrn_reflns_number 4011 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 66.0 _reflns_number_total 4011 _reflns_number_observed 2112 _reflns_observed_criterion >3sigma(F) _computing_data_collection 'Cad4 (Nonius)' _computing_cell_refinement 'Cad4 (Nonius)' _computing_data_reduction 'Molen (Nonius)' _computing_structure_solution 'SIR92 (Giacovazzo,1992)' _computing_structure_refinement 'Crystals (Watkin, 1997)' _computing_molecular_graphics 'Crystals (Watkin, 1997)' _computing_publication_material 'Crystals (Watkin, 1997)' _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme unit _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_number_reflns 2079 _refine_ls_number_parameters 327 _refine_ls_R_factor_obs 0.047 _refine_ls_wR_factor_obs 0.057 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type C2 0.09496(4) 0.4288(3) -0.01248(9) 0.0315 1.0000 Uani C3 0.12707(4) 0.4284(3) 0.00066(9) 0.0302 1.0000 Uani C4 0.14540(4) 0.2497(3) 0.05362(9) 0.0297 1.0000 Uani C5 0.13118(4) 0.0732(3) 0.09278(9) 0.0304 1.0000 Uani C6 0.09909(4) 0.0751(3) 0.0787(1) 0.0333 1.0000 Uani C7 0.07579(4) 0.6136(3) -0.0664(1) 0.0354 1.0000 Uani C12 0.08980(4) 0.7890(3) -0.10542(9) 0.0342 1.0000 Uani C13 0.14139(4) 0.6086(3) -0.03959(9) 0.0314 1.0000 Uani C14 0.12297(4) 0.7872(3) -0.09221(9) 0.0337 1.0000 Uani C18 0.17358(4) 0.6099(3) -0.0257(1) 0.0365 1.0000 Uani C19 0.17810(4) 0.2509(3) 0.06805(9) 0.0358 1.0000 Uani C20 0.19244(4) 0.4300(3) 0.0297(1) 0.0392 1.0000 Uani C24 0.19656(4) 0.0738(3) 0.1210(1) 0.0388 1.0000 Uani C25 0.14974(4) -0.1084(3) 0.14657(9) 0.0315 1.0000 Uani C26 0.18194(4) -0.1105(3) 0.1606(1) 0.0370 1.0000 Uani C30 0.13539(4) -0.2871(3) 0.18516(9) 0.0335 1.0000 Uani C31 0.08407(4) -0.1078(3) 0.1185(1) 0.0345 1.0000 Uani C32 0.10224(5) -0.2861(3) 0.17077(9) 0.0342 1.0000 Uani C1 0.08191(4) 0.2523(3) 0.0267(1) 0.0370 1.0000 Uani C8 0.04402(5) 0.6239(4) -0.0798(1) 0.0475 1.0000 Uani C9 0.02602(5) 0.7983(4) -0.1298(1) 0.0536 1.0000 Uani C10 0.03981(5) 0.9709(4) -0.1682(1) 0.0493 1.0000 Uani C11 0.07075(5) 0.9649(3) -0.1565(1) 0.0447 1.0000 Uani C15 0.13774(5) 0.9589(3) -0.1294(1) 0.0403 1.0000 Uani C16 0.16887(5) 0.9571(4) -0.1165(1) 0.0457 1.0000 Uani C17 0.18687(5) 0.7859(4) -0.0655(1) 0.0449 1.0000 Uani C21 0.22420(5) 0.4291(4) 0.0465(1) 0.0526 1.0000 Uani C22 0.24202(5) 0.2581(4) 0.0983(1) 0.0606 1.0000 Uani C23 0.22814(5) 0.0822(4) 0.1348(1) 0.0520 1.0000 Uani C27 0.19925(5) -0.2924(4) 0.2117(1) 0.0461 1.0000 Uani C28 0.18524(5) -0.4659(4) 0.2483(1) 0.0461 1.0000 Uani C29 0.15413(5) -0.4629(3) 0.2358(1) 0.0417 1.0000 Uani C33 0.08718(5) -0.4605(4) 0.2077(1) 0.0429 1.0000 Uani C34 0.05615(5) -0.4625(4) 0.1937(1) 0.0477 1.0000 Uani C35 0.03820(5) -0.2883(4) 0.1418(1) 0.0518 1.0000 Uani C36 0.05223(5) -0.1145(4) 0.1053(1) 0.0457 1.0000 Uani H11 0.06023(4) 0.2528(3) 0.0173(1) 0.054(2) 1.0000 Uiso H81 0.03461(5) 0.5062(4) -0.0534(1) 0.068(2) 1.0000 Uiso H91 0.00442(5) 0.8025(4) -0.1377(1) 0.073(2) 1.0000 Uiso H101 0.02767(5) 1.0922(4) -0.2028(1) 0.072(2) 1.0000 Uiso H111 0.07983(5) 1.0830(3) -0.1836(1) 0.064(2) 1.0000 Uiso H151 0.12573(5) 1.0783(3) -0.1649(1) 0.062(2) 1.0000 Uiso H161 0.17825(5) 1.0760(4) -0.1426(1) 0.066(2) 1.0000 Uiso H171 0.20851(5) 0.7867(4) -0.0568(1) 0.064(2) 1.0000 Uiso H211 0.23390(5) 0.5479(4) 0.0211(1) 0.074(2) 1.0000 Uiso H221 0.26374(5) 0.2637(4) 0.1092(1) 0.082(2) 1.0000 Uiso H231 0.24054(5) -0.0362(4) 0.1700(1) 0.073(2) 1.0000 Uiso H271 0.22093(5) -0.2950(4) 0.2210(1) 0.066(2) 1.0000 Uiso H281 0.19729(5) -0.5877(4) 0.2830(1) 0.066(2) 1.0000 Uiso H291 0.14483(5) -0.5833(3) 0.2617(1) 0.063(2) 1.0000 Uiso H331 0.09919(5) -0.5797(4) 0.2433(1) 0.063(2) 1.0000 Uiso H341 0.04669(5) -0.5813(4) 0.2197(1) 0.071(2) 1.0000 Uiso H351 0.01650(5) -0.2897(4) 0.1319(1) 0.073(2) 1.0000 Uiso H361 0.03999(5) 0.0028(4) 0.0694(1) 0.066(2) 1.0000 Uiso 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 C2 0.053(1) 0.0167(8) 0.0353(9) -0.0021(7) 0.0115(8) -0.0003(7) C3 0.054(1) 0.0162(8) 0.0325(8) -0.0038(7) 0.0127(8) -0.0029(7) C4 0.051(1) 0.0168(8) 0.0328(8) -0.0050(7) 0.0124(7) -0.0028(7) C5 0.055(1) 0.0173(8) 0.0313(8) -0.0047(7) 0.0119(8) -0.0017(7) C6 0.054(1) 0.0197(8) 0.0366(9) -0.0035(7) 0.0141(8) -0.0033(7) C7 0.056(1) 0.0200(8) 0.0396(9) -0.0023(7) 0.0121(8) -0.0003(7) C12 0.061(1) 0.0193(8) 0.0350(8) -0.0038(7) 0.0129(8) 0.0013(7) C13 0.057(1) 0.0177(8) 0.0331(9) -0.0050(7) 0.0144(8) -0.0034(7) C14 0.063(1) 0.0196(8) 0.0334(8) -0.0037(7) 0.0160(8) -0.0029(7) C18 0.057(1) 0.0243(9) 0.0374(9) -0.0037(7) 0.0146(8) -0.0055(7) C19 0.053(1) 0.0248(8) 0.0362(8) -0.0055(7) 0.0127(8) -0.0016(7) C20 0.053(1) 0.0275(9) 0.043(1) -0.0035(8) 0.0150(8) -0.0059(8) C24 0.052(1) 0.0273(9) 0.0401(9) -0.0026(7) 0.0103(8) 0.0004(8) C25 0.058(1) 0.0168(8) 0.0319(8) -0.0021(7) 0.0114(8) 0.0004(7) C26 0.056(1) 0.0254(9) 0.0351(8) -0.0024(7) 0.0095(8) 0.0026(8) C30 0.063(1) 0.0187(8) 0.0326(8) -0.0030(7) 0.0131(8) 0.0001(8) C31 0.058(1) 0.0192(8) 0.0395(9) -0.0026(7) 0.0162(8) -0.0041(7) C32 0.066(1) 0.0192(8) 0.0351(9) -0.0038(7) 0.0177(8) -0.0053(8) C1 0.049(1) 0.0242(8) 0.0430(9) 0.0011(8) 0.0131(8) -0.0004(8) C8 0.058(1) 0.031(1) 0.059(1) 0.0081(9) 0.014(1) 0.0017(9) C9 0.059(1) 0.040(1) 0.064(1) 0.006(1) 0.012(1) 0.0068(9) C10 0.068(1) 0.034(1) 0.053(1) 0.0083(9) 0.010(1) 0.0103(9) C11 0.072(1) 0.0300(9) 0.042(1) 0.0057(8) 0.0151(9) 0.0033(9) C15 0.072(1) 0.0233(9) 0.0410(9) 0.0032(8) 0.0167(9) -0.0035(9) C16 0.071(1) 0.033(1) 0.048(1) 0.0033(9) 0.021(1) -0.0128(9) C17 0.059(1) 0.035(1) 0.047(1) 0.0008(9) 0.0166(9) -0.0105(9) C21 0.056(1) 0.045(1) 0.064(1) 0.007(1) 0.020(1) -0.0074(9) C22 0.050(1) 0.060(1) 0.076(1) 0.013(1) 0.015(1) 0.000(1) C23 0.054(1) 0.043(1) 0.058(1) 0.007(1) 0.009(1) 0.0031(9) C27 0.060(1) 0.037(1) 0.044(1) 0.0030(8) 0.0110(9) 0.0080(9) C28 0.072(1) 0.032(1) 0.044(1) 0.0067(9) 0.012(1) 0.0109(9) C29 0.075(1) 0.0244(9) 0.041(1) 0.0036(8) 0.018(1) 0.0008(9) C33 0.072(1) 0.0257(9) 0.047(1) 0.0036(8) 0.019(1) -0.0068(8) C34 0.079(1) 0.031(1) 0.054(1) 0.0038(9) 0.027(1) -0.0121(9) C35 0.064(1) 0.039(1) 0.067(1) 0.002(1) 0.026(1) -0.011(1) C36 0.061(1) 0.029(1) 0.057(1) 0.0054(9) 0.020(1) -0.0037(8) _refine_ls_extinction_coef 16.6(41) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C2 . C3 . 1.409(3) yes C2 . C7 . 1.470(2) yes C2 . C1 . 1.392(2) yes C3 . C4 . 1.426(2) yes C3 . C13 . 1.449(2) yes C4 . C5 . 1.422(2) yes C4 . C19 . 1.433(2) yes C5 . C6 . 1.406(3) yes C5 . C25 . 1.447(2) yes C6 . C31 . 1.473(2) yes C6 . C1 . 1.391(2) yes C7 . C12 . 1.410(2) yes C7 . C8 . 1.394(3) yes C12 . C14 . 1.456(3) yes C12 . C11 . 1.413(2) yes C13 . C14 . 1.424(2) yes C13 . C18 . 1.411(3) yes C14 . C15 . 1.398(2) yes C18 . C20 . 1.463(3) yes C18 . C17 . 1.403(2) yes C19 . C20 . 1.424(2) yes C19 . C24 . 1.422(2) yes C20 . C21 . 1.387(3) yes C24 . C26 . 1.464(2) yes C24 . C23 . 1.384(3) yes C25 . C26 . 1.411(3) yes C25 . C30 . 1.426(2) yes C26 . C27 . 1.402(2) yes C30 . C32 . 1.453(3) yes C30 . C29 . 1.402(2) yes C31 . C32 . 1.415(2) yes C31 . C36 . 1.397(3) yes C32 . C33 . 1.412(3) yes C8 . C9 . 1.378(3) yes C9 . C10 . 1.389(3) yes C10 . C11 . 1.360(3) yes C15 . C16 . 1.366(3) yes C16 . C17 . 1.376(3) yes C21 . C22 . 1.380(3) yes C22 . C23 . 1.381(3) yes C27 . C28 . 1.378(3) yes C28 . C29 . 1.365(3) yes C33 . C34 . 1.359(3) yes C34 . C35 . 1.394(3) yes C35 . C36 . 1.378(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . C2 . C7 . 120.3(1) no C3 . C2 . C1 . 118.7(2) no C7 . C2 . C1 . 121.0(2) no C2 . C3 . C4 . 119.7(2) no C2 . C3 . C13 . 120.1(2) no C4 . C3 . C13 . 120.2(2) no C3 . C4 . C5 . 119.8(2) no C3 . C4 . C19 . 119.9(1) no C5 . C4 . C19 . 120.2(2) no C4 . C5 . C6 . 119.8(2) no C4 . C5 . C25 . 119.9(2) no C6 . C5 . C25 . 120.3(2) no C5 . C6 . C31 . 120.3(2) no C5 . C6 . C1 . 118.9(2) no C31 . C6 . C1 . 120.8(2) no C2 . C7 . C12 . 119.4(2) no C2 . C7 . C8 . 122.0(2) no C12 . C7 . C8 . 118.5(2) no C7 . C12 . C14 . 120.2(2) no C7 . C12 . C11 . 118.0(2) no C14 . C12 . C11 . 121.7(2) no C3 . C13 . C14 . 119.9(2) no C3 . C13 . C18 . 120.1(2) no C14 . C13 . C18 . 120.0(2) no C12 . C14 . C13 . 120.0(2) no C12 . C14 . C15 . 122.0(2) no C13 . C14 . C15 . 118.0(2) no C13 . C18 . C20 . 119.8(2) no C13 . C18 . C17 . 118.9(2) no C20 . C18 . C17 . 121.3(2) no C4 . C19 . C20 . 120.3(2) no C4 . C19 . C24 . 120.3(2) no C20 . C19 . C24 . 119.4(2) no C18 . C20 . C19 . 119.7(2) no C18 . C20 . C21 . 121.7(2) no C19 . C20 . C21 . 118.6(2) no C19 . C24 . C26 . 119.6(2) no C19 . C24 . C23 . 119.1(2) no C26 . C24 . C23 . 121.3(2) no C5 . C25 . C26 . 120.3(2) no C5 . C25 . C30 . 119.8(2) no C26 . C25 . C30 . 119.9(2) no C24 . C26 . C25 . 119.7(2) no C24 . C26 . C27 . 121.3(2) no C25 . C26 . C27 . 119.0(2) no C25 . C30 . C32 . 120.1(2) no C25 . C30 . C29 . 118.1(2) no C32 . C30 . C29 . 121.8(2) no C6 . C31 . C32 . 119.3(2) no C6 . C31 . C36 . 122.0(2) no C32 . C31 . C36 . 118.6(2) no C30 . C32 . C31 . 120.2(2) no C30 . C32 . C33 . 121.8(2) no C31 . C32 . C33 . 118.1(2) no C2 . C1 . C6 . 123.1(2) no C7 . C8 . C9 . 122.2(2) no C8 . C9 . C10 . 119.3(2) no C9 . C10 . C11 . 119.9(2) no C12 . C11 . C10 . 122.1(2) no C14 . C15 . C16 . 121.7(2) no C15 . C16 . C17 . 120.7(2) no C18 . C17 . C16 . 120.6(2) no C20 . C21 . C22 . 121.7(2) no C21 . C22 . C23 . 119.7(2) no C24 . C23 . C22 . 121.4(2) no C26 . C27 . C28 . 120.8(2) no C27 . C28 . C29 . 120.5(2) no C30 . C29 . C28 . 121.7(2) no C32 . C33 . C34 . 122.0(2) no C33 . C34 . C35 . 120.0(2) no C34 . C35 . C36 . 119.4(2) no C31 . C36 . C35 . 121.9(2) no #==============================================================================