# Perkin Transactions II © The Royal Society of Chemistry, 1999 # CCDC Number: 188/172 #============================================================================== data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Voigt-Martin, Ingrid G. Institut f\"ur Physikalische Chemie der Universit\"at Mainz Welder Weg 11, D-55099 Mainz, Germany ; _publ_contact_author_phone '+49 06131 393148' _publ_contact_author_fax '+49 06131 393768' _publ_contact_author_email voigtma@mail.uni-mainz.de _publ_requested_journal 'Journal. of Chem. Soc. Perkin Trans. II' _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figure has been sent to Prof Hall (Co-editor, Acta Cryst., Univ. Western Australia) and structure factor listings can be made available if requested. ; # 3. TITLE AND AUTHOR LIST _publ_section_title ; Tetrabenzo[ab,f,jk,o][18]annulene:synthesis, crystal structure analysis, ab initio quantum - chemical studies of intermolecular interactions in the gas phase and in crystalline states, photodimerization and photopolymerization ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Yu, Richeng' ; Institut f\"ur Physikalische Chemie der Universit\"at Mainz Welderweg 11 55099 Mainz Federal Republic of Germany ; 'Yakimansky, Alexander V.' ; Institute of Macromolecular Compounds of Russian Academy of Sciences Bolshoi pr. 31 199004 St. Petersburg Russia ; 'Voigt-Martin, Ingrid G.' ; Institut f\"ur Physikalische Chemie der Universit\"at Mainz Welderweg 11 55099 Mainz Federal Republic of Germany ; 'Fetten, Michael' ; Institut f\"ur Organische Chemie der Universit\"at Mainz Duesbergweg 10-14 55099 Mainz Federal Republic of Germany ; 'Schnorpfeil, C.' ; Institut f\"ur Organische Chemie der Universit\"at Mainz Duesbergweg 10-14 55099 Mainz Federal Republic of Germany ; 'Schollmeyer, Dieter' ; Institut f\"ur Organische Chemie der Universit\"at Mainz Duesbergweg 10-14 55099 Mainz Federal Republic of Germany ; 'Meier, Herbert' ; Institut f\"ur Organische Chemie der Universit\"at Mainz Duesbergweg 10-14 55099 Mainz Federal Republic of Germany ; data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24' _chemical_formula_weight 408.54 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 28.1031(12) _cell_length_b 28.1031(12) _cell_length_c 7.1509(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4891.0(4) _cell_formula_units_Z 9 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 40 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 0.532 _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 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf Nonius' _diffrn_measurement_method \q/2\w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_reflns_number 2783 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 74.84 _reflns_number_total 2234 _reflns_number_gt 1485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius Software V5' _computing_cell_refinement 'Enraf Nonius Software V5' _computing_data_reduction 'Corinc (Dr\"ager, 1971)' _computing_structure_solution 'Sir-92 (Altomare,1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0581P)^2^+1.3084P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'riding refU' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2234 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _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 0.22021(9) 0.12794(9) 0.6826(3) 0.0404(5) Uani 1 1 d . . . H1 H 0.2609 0.1393 0.6691 0.055(7) Uiso 1 1 d R . . C2 C 0.19134(8) 0.09789(8) 0.8389(3) 0.0388(5) Uani 1 1 d . . . C3 C 0.13503(9) 0.07956(9) 0.8483(3) 0.0445(5) Uani 1 1 d . . . H3 H 0.1120 0.0606 0.9603 0.051(6) Uiso 1 1 d R . . C4 C 0.10937(9) 0.09141(10) 0.7049(3) 0.0485(6) Uani 1 1 d . . . H4 H 0.0670 0.0781 0.7213 0.051(7) Uiso 1 1 d R . . C5 C 0.13848(9) 0.12093(9) 0.5510(3) 0.0430(5) Uani 1 1 d . . . H5 H 0.1204 0.1291 0.4394 0.042(6) Uiso 1 1 d R . . C6 C 0.19506(8) 0.14039(8) 0.5375(3) 0.0390(5) Uani 1 1 d . . . C7 C 0.22582(9) 0.17061(9) 0.3710(3) 0.0422(5) Uani 1 1 d . . . H7 H 0.2034 0.1662 0.2679 0.057(7) Uiso 1 1 d R . . C8 C 0.28010(9) 0.20088(9) 0.3589(3) 0.0413(5) Uani 1 1 d . . . H8 H 0.2984 0.2031 0.4740 0.047(6) Uiso 1 1 d R . . C9 C 0.31179(9) 0.22758(8) 0.1894(3) 0.0388(5) Uani 1 1 d . . . C10 C 0.28733(10) 0.23983(9) 0.0399(3) 0.0467(5) Uani 1 1 d . . . H10 H 0.2506 0.2362 0.0686 0.058(7) Uiso 1 1 d R . . C11 C 0.31518(10) 0.26170(9) -0.1243(3) 0.0496(6) Uani 1 1 d . . . H11 H 0.2943 0.2664 -0.2307 0.066(8) Uiso 1 1 d R . . C12 C 0.36834(10) 0.27164(9) -0.1461(3) 0.0466(5) Uani 1 1 d . . . H12 H 0.3856 0.2891 -0.2685 0.059(7) Uiso 1 1 d R . . C13 C 0.39388(9) 0.26124(9) 0.0008(3) 0.0435(5) Uani 1 1 d . . . H13 H 0.4347 0.2721 -0.0080 0.055(7) Uiso 1 1 d R . . C14 C 0.36695(9) 0.23987(8) 0.1703(3) 0.0378(5) Uani 1 1 d . . . C15 C 0.39492(9) 0.22799(9) 0.3229(3) 0.0399(5) Uani 1 1 d . . . H15 H 0.3705 0.2024 0.4210 0.044(6) Uiso 1 1 d R . . C16 C 0.44850(9) 0.24905(9) 0.3427(3) 0.0429(5) Uani 1 1 d . . . H16 H 0.4729 0.2758 0.2400 0.062(7) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0348(11) 0.0440(12) 0.0413(11) 0.0017(9) 0.0004(8) 0.0189(10) C2 0.0390(11) 0.0397(11) 0.0383(10) -0.0039(9) -0.0010(8) 0.0201(10) C3 0.0403(12) 0.0507(13) 0.0424(11) 0.0007(9) 0.0026(9) 0.0226(10) C4 0.0391(12) 0.0553(14) 0.0544(13) -0.0031(11) 0.0003(10) 0.0260(11) C5 0.0400(12) 0.0488(13) 0.0460(12) -0.0016(9) -0.0050(9) 0.0266(10) C6 0.0411(12) 0.0393(11) 0.0407(11) -0.0029(8) -0.0025(9) 0.0231(10) C7 0.0429(12) 0.0483(13) 0.0403(11) 0.0018(9) -0.0046(9) 0.0266(10) C8 0.0428(12) 0.0481(12) 0.0369(10) 0.0037(9) -0.0013(9) 0.0257(10) C9 0.0432(12) 0.0366(11) 0.0362(10) 0.0008(8) -0.0002(9) 0.0198(9) C10 0.0498(13) 0.0515(13) 0.0426(11) 0.0036(10) -0.0043(10) 0.0281(11) C11 0.0589(15) 0.0508(14) 0.0415(11) 0.0052(10) -0.0077(11) 0.0293(12) C12 0.0535(14) 0.0432(12) 0.0378(11) 0.0046(9) 0.0019(10) 0.0201(11) C13 0.0447(12) 0.0419(12) 0.0424(12) 0.0023(9) 0.0000(9) 0.0205(10) C14 0.0408(11) 0.0351(11) 0.0361(10) -0.0002(8) -0.0025(8) 0.0180(9) C15 0.0398(11) 0.0417(12) 0.0369(10) 0.0033(9) 0.0006(9) 0.0195(10) C16 0.0420(12) 0.0432(12) 0.0386(10) 0.0046(9) 0.0015(9) 0.0176(10) _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 1.391(3) . ? C1 C6 1.395(3) . ? C1 H1 1.0272 . ? C2 C3 1.399(3) . ? C2 C16 1.476(3) 13_556 ? C3 C4 1.387(3) . ? C3 H3 0.9993 . ? C4 C5 1.374(3) . ? C4 H4 1.0612 . ? C5 C6 1.402(3) . ? C5 H5 1.0317 . ? C6 C7 1.467(3) . ? C7 C8 1.327(3) . ? C7 H7 0.9370 . ? C8 C9 1.469(3) . ? C8 H8 0.9556 . ? C9 C10 1.404(3) . ? C9 C14 1.416(3) . ? C10 C11 1.374(3) . ? C10 H10 1.0054 . ? C11 C12 1.385(3) . ? C11 H11 1.0091 . ? C12 C13 1.384(3) . ? C12 H12 1.0021 . ? C13 C14 1.396(3) . ? C13 H13 1.0299 . ? C14 C15 1.477(3) . ? C15 C16 1.321(3) . ? C15 H15 0.9941 . ? C16 C2 1.476(3) 13_556 ? C16 H16 1.0288 . ? 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 C6 122.33(19) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 118.5 . . ? C1 C2 C3 118.10(19) . . ? C1 C2 C16 121.94(19) . 13_556 ? C3 C2 C16 119.95(19) . 13_556 ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 116.5 . . ? C2 C3 H3 123.0 . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 121.7 . . ? C3 C4 H4 117.4 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 122.9 . . ? C6 C5 H5 116.6 . . ? C1 C6 C5 117.9(2) . . ? C1 C6 C7 121.54(19) . . ? C5 C6 C7 120.45(19) . . ? C8 C7 C6 125.44(19) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 113.6 . . ? C7 C8 C9 126.2(2) . . ? C7 C8 H8 113.3 . . ? C9 C8 H8 120.5 . . ? C10 C9 C14 118.51(19) . . ? C10 C9 C8 120.5(2) . . ? C14 C9 C8 120.96(18) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 123.1 . . ? C9 C10 H10 115.0 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 117.7 . . ? C12 C11 H11 121.9 . . ? C13 C12 C11 119.5(2) . . ? C13 C12 H12 126.2 . . ? C11 C12 H12 114.0 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 117.6 . . ? C13 C14 C9 118.72(19) . . ? C13 C14 C15 120.21(19) . . ? C9 C14 C15 121.00(18) . . ? C16 C15 C14 126.45(19) . . ? C16 C15 H15 117.9 . . ? C14 C15 H15 115.6 . . ? C15 C16 C2 125.3(2) . 13_556 ? C15 C16 H16 116.3 . . ? C2 C16 H16 118.3 13_556 . ? 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 C6 C1 C2 C3 0.3(3) . . . . ? C6 C1 C2 C16 179.2(2) . . . 13_556 ? C1 C2 C3 C4 -0.1(3) . . . . ? C16 C2 C3 C4 -178.9(2) 13_556 . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C2 C1 C6 C7 -178.0(2) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C4 C5 C6 C7 178.3(2) . . . . ? C1 C6 C7 C8 -18.5(3) . . . . ? C5 C6 C7 C8 164.4(2) . . . . ? C6 C7 C8 C9 174.5(2) . . . . ? C7 C8 C9 C10 23.1(3) . . . . ? C7 C8 C9 C14 -154.8(2) . . . . ? C14 C9 C10 C11 2.0(3) . . . . ? C8 C9 C10 C11 -175.9(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C13 -2.3(3) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? C12 C13 C14 C9 1.4(3) . . . . ? C12 C13 C14 C15 178.5(2) . . . . ? C10 C9 C14 C13 -2.9(3) . . . . ? C8 C9 C14 C13 175.0(2) . . . . ? C10 C9 C14 C15 179.94(19) . . . . ? C8 C9 C14 C15 -2.2(3) . . . . ? C13 C14 C15 C16 20.9(3) . . . . ? C9 C14 C15 C16 -162.0(2) . . . . ? C14 C15 C16 C2 -178.5(2) . . . 13_556 ? _diffrn_measured_fraction_theta_max 1.001 _diffrn_reflns_theta_full 74.84 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.147 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.036