# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1376 data_TPTT #------------------------------------------------------------------------------ _audit_creation_date 'Thu Jul 15 12:30:44 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'Rigaku/AFC Diffractometer Control' _computing_cell_refinement 'Rigaku/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL93' _computing_publication_material 'teXsan' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 318.43 _chemical_formula_analytical 'C18 H6 S3 ' _chemical_formula_sum 'C18 H6 S3 ' _chemical_formula_moiety 'C18 H6 S3 ' _chemical_formula_structural ? _chemical_melting_point '> 300 deg ' #------------------------------------------------------------------------------ _cell_length_a 26.121(7) _cell_length_b 26.121(7) _cell_length_c 7.433(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 4392(1) _cell_formula_units_Z 14 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 7.1 #------------------------------------------------------------------------------ _symmetry_cell_setting hexgonal _symmetry_space_group_name_H-M 'P 6 c c ' _symmetry_Int_Tables_number 184 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x-y,z -x+y,-x,z -x,-y,z y,-x+y,z x-y,x,z y,x,1/2+z -x,-x+y,1/2+z x-y,-y,1/2+z -y,-x,1/2+z x,x-y,1/2+z -x+y,y,1/2+z #------------------------------------------------------------------------------ _exptl_crystal_description 'needles' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.850 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2268.00 _exptl_absorpt_coefficient_mu 0.576 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.999 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_decay_% 0.20 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 2 2 -2 2 -2 0 2 _diffrn_reflns_number 1820 _reflns_number_total 1820 _reflns_number_gt 698 _reflns_observed_expression >1.7sigma(I) _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.252 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 27.50 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.02545 _diffrn_orient_matrix_UB_12 -0.04280 _diffrn_orient_matrix_UB_13 0.03047 _diffrn_orient_matrix_UB_21 0.03547 _diffrn_orient_matrix_UB_22 -0.00509 _diffrn_orient_matrix_UB_23 -0.00379 _diffrn_orient_matrix_UB_31 0.00695 _diffrn_orient_matrix_UB_32 0.00981 _diffrn_orient_matrix_UB_33 0.13099 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'S' 'S' 0.125 0.123 ;International Tables for Crystallography (1992, 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_flags _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.7117(2) 0.2810(2) 0.3611(7) 0.057(1) Uani 1.00 d . . . S(2) S 0.5990(2) 0.0141(2) 0.1925(6) 0.057(1) Uani 1.00 d . . . S(3) S 0.8657(2) 0.1627(2) 0.3670(7) 0.054(1) Uani 1.00 d . . . S(4) S 0.9648(7) 0.1158(5) 0.060(2) 0.065(3) Uani 0.50 d P . . C(1) C 0.7790(6) 0.1797(6) 0.447(2) 0.04390(5) Uiso 1.00 d . . . C(2) C 0.7433(6) 0.2053(7) 0.448(2) 0.04067(5) Uiso 1.00 d . . . C(3) C 0.6844(6) 0.1731(7) 0.405(2) 0.04854(6) Uiso 1.00 d . . . C(4) C 0.6592(6) 0.1134(5) 0.369(2) 0.03880(4) Uiso 1.00 d . . . C(5) C 0.6940(5) 0.0859(5) 0.367(2) 0.03765(4) Uiso 1.00 d . . . C(6) C 0.7524(6) 0.1185(6) 0.407(2) 0.03692(5) Uiso 1.00 d . . . C(7) C 0.8398(6) 0.2119(6) 0.427(2) 0.03740(5) Uiso 1.00 d . . . C(8) C 0.8672(7) 0.2752(7) 0.418(2) 0.05988(6) Uiso 1.00 d . . . C(9) C 0.8299(7) 0.3015(7) 0.419(2) 0.05346(6) Uiso 1.00 d . . . C(10) C 0.7693(6) 0.2661(6) 0.424(2) 0.04059(5) Uiso 1.00 d . . . C(11) C 0.6566(6) 0.2032(6) 0.346(3) 0.05453(5) Uiso 1.00 d . . . C(12) C 0.6037(7) 0.1754(7) 0.259(2) 0.05380(6) Uiso 1.00 d . . . C(13) C 0.5769(6) 0.1131(7) 0.219(3) 0.05394(6) Uiso 1.00 d . . . C(14) C 0.6076(6) 0.0829(6) 0.273(2) 0.04412(5) Uiso 1.00 d . . . C(15) C 0.6714(6) 0.0335(6) 0.273(2) 0.03973(5) Uiso 1.00 d . . . C(16) C 0.7088(7) 0.0110(7) 0.233(2) 0.05519(6) Uiso 1.00 d . . . C(17) C 0.7691(7) 0.0440(7) 0.276(2) 0.05770(6) Uiso 1.00 d . . . C(18) C 0.7918(5) 0.1006(5) 0.354(3) 0.03990(4) Uiso 1.00 d . . . C(19) C 1.0182(6) 0.0597(5) 0.156(2) 0.04136(5) Uiso 1.00 d . . . C(20) C 1.0353(8) 0.1165(8) 0.096(3) 0.06722(7) Uiso 1.00 d . . . C(21) C 0.998(2) 0.139(1) 0.042(5) 0.0370(1) Uiso 0.50 d P . . C(22) C 0.934(1) 0.085(2) 0.063(5) 0.0385(1) Uiso 0.50 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.075(3) 0.054(3) 0.051(2) 0.040(2) -0.010(3) -0.008(3) S(2) 0.049(2) 0.059(3) 0.044(2) 0.013(2) -0.003(2) -0.005(2) S(3) 0.047(2) 0.063(3) 0.054(3) 0.029(2) 0.001(3) -0.005(3) S(4) 0.12(1) 0.042(8) 0.048(7) 0.056(9) 0.009(8) -0.003(6) #------------------------------------------------------------------------------ _refine_special_details ; Refinement based on F against all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F, conventional R-factors (R) are calculated on F, with F set to zero for negative F. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. thus the refinement was done using all reflections. ; _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^) + (0.0818P)^2^+6.8236P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002 _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack -0.2(5) _refine_ls_number_reflns 698 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2936 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.2502 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.0250 _refine_ls_shift/su_mean 0.0030 _refine_diff_density_min -0.44 _refine_diff_density_max 0.47 _refine_diff_density_rms 0.10 #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 S(1) C(10) 1.80(2) 1_555 1_555 yes S(1) C(11) 1.81(1) 1_555 1_555 yes S(2) C(14) 1.80(2) 1_555 1_555 yes S(2) C(15) 1.80(2) 1_555 1_555 yes S(3) C(7) 1.78(2) 1_555 1_555 yes S(3) C(18) 1.80(1) 1_555 1_555 yes S(4) C(20) 1.85(3) 1_555 1_555 yes S(4) C(20) 1.85(2) 1_555 6_545 yes S(4) C(21) 0.78(4) 1_555 1_555 yes S(4) C(22) 0.80(3) 1_555 1_555 yes C(1) C(2) 1.39(3) 1_555 1_555 yes C(1) C(6) 1.42(2) 1_555 1_555 yes C(1) C(7) 1.38(2) 1_555 1_555 yes C(2) C(3) 1.37(2) 1_555 1_555 yes C(2) C(10) 1.39(2) 1_555 1_555 yes C(3) C(4) 1.38(2) 1_555 1_555 yes C(3) C(11) 1.38(3) 1_555 1_555 yes C(4) C(5) 1.41(2) 1_555 1_555 yes C(4) C(14) 1.37(2) 1_555 1_555 yes C(5) C(6) 1.36(2) 1_555 1_555 yes C(5) C(15) 1.38(2) 1_555 1_555 yes C(6) C(18) 1.38(2) 1_555 1_555 yes C(7) C(8) 1.44(2) 1_555 1_555 yes C(8) C(9) 1.44(3) 1_555 1_555 yes C(9) C(10) 1.38(2) 1_555 1_555 yes C(11) C(12) 1.36(2) 1_555 1_555 yes C(12) C(13) 1.44(2) 1_555 1_555 yes C(13) C(14) 1.44(3) 1_555 1_555 yes C(15) C(16) 1.40(3) 1_555 1_555 yes C(16) C(17) 1.40(2) 1_555 1_555 yes C(17) C(18) 1.41(2) 1_555 1_555 yes C(19) C(19) 1.39(1) 1_555 6_545 yes C(19) C(19) 1.39(1) 1_555 5_665 yes C(19) C(20) 1.39(2) 1_555 1_555 yes C(20) C(21) 1.43(6) 1_555 1_555 yes C(20) C(22) 1.19(5) 1_555 5_665 yes C(21) C(22) 1.56(4) 1_555 1_555 yes #------------------------------------------------------------------------------ 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 C(10) S(1) C(11) 93.1(8) 1_555 1_555 1_555 yes C(14) S(2) C(15) 91.0(8) 1_555 1_555 1_555 yes C(7) S(3) C(18) 92.3(7) 1_555 1_555 1_555 yes C(20) S(4) C(20) 93(1) 1_555 1_555 6_545 yes C(20) S(4) C(21) 46(3) 1_555 1_555 1_555 yes C(20) S(4) C(22) 120(3) 1_555 1_555 1_555 yes C(20) S(4) C(21) 138(4) 6_545 1_555 1_555 yes C(20) S(4) C(22) 27(3) 6_545 1_555 1_555 yes C(21) S(4) C(22) 161(5) 1_555 1_555 1_555 yes C(2) C(1) C(6) 118(1) 1_555 1_555 1_555 yes C(2) C(1) C(7) 123(1) 1_555 1_555 1_555 yes C(6) C(1) C(7) 115(1) 1_555 1_555 1_555 yes C(1) C(2) C(3) 121(1) 1_555 1_555 1_555 yes C(1) C(2) C(10) 118(1) 1_555 1_555 1_555 yes C(3) C(2) C(10) 115(1) 1_555 1_555 1_555 yes C(2) C(3) C(4) 119(1) 1_555 1_555 1_555 yes C(2) C(3) C(11) 118(1) 1_555 1_555 1_555 yes C(4) C(3) C(11) 119(1) 1_555 1_555 1_555 yes C(3) C(4) C(5) 120(1) 1_555 1_555 1_555 yes C(3) C(4) C(14) 122(1) 1_555 1_555 1_555 yes C(5) C(4) C(14) 113(1) 1_555 1_555 1_555 yes C(4) C(5) C(6) 119(1) 1_555 1_555 1_555 yes C(4) C(5) C(15) 116(1) 1_555 1_555 1_555 yes C(6) C(5) C(15) 121(1) 1_555 1_555 1_555 yes C(1) C(6) C(5) 120(1) 1_555 1_555 1_555 yes C(1) C(6) C(18) 114(1) 1_555 1_555 1_555 yes C(5) C(6) C(18) 121(1) 1_555 1_555 1_555 yes S(3) C(7) C(1) 108(1) 1_555 1_555 1_555 yes S(3) C(7) C(8) 131(1) 1_555 1_555 1_555 yes C(1) C(7) C(8) 117(1) 1_555 1_555 1_555 yes C(7) C(8) C(9) 118(1) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120(1) 1_555 1_555 1_555 yes S(1) C(10) C(2) 107.2(10) 1_555 1_555 1_555 yes S(1) C(10) C(9) 130(1) 1_555 1_555 1_555 yes C(2) C(10) C(9) 120(1) 1_555 1_555 1_555 yes S(1) C(11) C(3) 105(1) 1_555 1_555 1_555 yes S(1) C(11) C(12) 130(1) 1_555 1_555 1_555 yes C(3) C(11) C(12) 121(1) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119(1) 1_555 1_555 1_555 yes C(12) C(13) C(14) 118(1) 1_555 1_555 1_555 yes S(2) C(14) C(4) 110(1) 1_555 1_555 1_555 yes S(2) C(14) C(13) 129(1) 1_555 1_555 1_555 yes C(4) C(14) C(13) 118(1) 1_555 1_555 1_555 yes S(2) C(15) C(5) 108(1) 1_555 1_555 1_555 yes S(2) C(15) C(16) 131(1) 1_555 1_555 1_555 yes C(5) C(15) C(16) 118(1) 1_555 1_555 1_555 yes C(15) C(16) C(17) 119(1) 1_555 1_555 1_555 yes C(16) C(17) C(18) 119(1) 1_555 1_555 1_555 yes S(3) C(18) C(6) 108.9(10) 1_555 1_555 1_555 yes S(3) C(18) C(17) 131(1) 1_555 1_555 1_555 yes C(6) C(18) C(17) 118(1) 1_555 1_555 1_555 yes C(19) C(19) C(19) 120.00(1) 6_545 1_555 5_665 yes C(19) C(19) C(20) 118(1) 6_545 1_555 1_555 yes C(19) C(19) C(20) 118(1) 5_665 1_555 1_555 yes S(4) C(20) S(4) 150(1) 1_555 1_555 5_665 yes S(4) C(20) C(19) 104(1) 1_555 1_555 1_555 yes S(4) C(20) C(21) 23(1) 1_555 1_555 1_555 yes S(4) C(20) C(22) 133(2) 1_555 1_555 5_665 yes S(4) C(20) C(19) 104(1) 5_665 1_555 1_555 yes S(4) C(20) C(21) 127(1) 5_665 1_555 1_555 yes S(4) C(20) C(22) 17(1) 5_665 1_555 5_665 yes C(19) C(20) C(21) 127(1) 1_555 1_555 1_555 yes C(19) C(20) C(22) 122(2) 1_555 1_555 5_665 yes C(21) C(20) C(22) 109(2) 1_555 1_555 5_665 yes S(4) C(21) C(20) 110(4) 1_555 1_555 1_555 yes S(4) C(21) C(22) 9(2) 1_555 1_555 1_555 yes C(20) C(21) C(22) 104(2) 1_555 1_555 1_555 yes S(4) C(22) C(20) 135(5) 1_555 1_555 6_545 yes S(4) C(22) C(21) 8(2) 1_555 1_555 1_555 yes C(20) C(22) C(21) 128(4) 6_545 1_555 1_555 yes #------------------------------------------------------------------------------ _publ_contact_author_name ' Tetsuo Otsubo' _publ_contact_author_address ; Department of Applied Chemistry, Faculty of Engineering Hiroshima University Higashi-Hiroshima 739-8527, Japan ; _publ_contact_author_email ' otsubo@ipc.hiroshima-u.ac.jp ' _publ_contact_author_fax ' +81-824-22-7191 ' _publ_contact_author_phone ' +81-824-24-7733 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal ' Chemical Communications' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? _publ_section_title ; Triphenyleno[1,12-bcd:4,5-b'c'd':8,9-b"c"d"]trithiophene: the first bowl-shaped heteroaromatic ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; _publ_section_synopsis ; ENTER SYNOPSIS ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1998). teXsan. Single Crystal Structure Analysis Software. Version 1.9. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ;