Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jay S. Siegel' 'Eric L. Elliott' 'Peter Gantzel' 'Daiki Hasegawa' 'Akihiro Orita' 'Junzo Otera' _publ_contact_author_name 'Prof Jay S. Siegel' _publ_contact_author_address ; Organic Chemistry Institute University of Zurich Winterthuererstr 190 Zurich CH-8057 SWITZERLAND ; _publ_contact_author_email JSS@OCI.UNIZH.CH _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis and properties of 1,6,7,12,13,18,19,24-octamethyl-dibenzo[def,pqr]tetraphenylene ; data_a _database_code_depnum_ccdc_archive 'CCDC 255954' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H40' _chemical_formula_weight 664.84 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+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.705(2) _cell_length_b 21.289(2) _cell_length_c 19.354(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.336(3) _cell_angle_gamma 90.00 _cell_volume 7250.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2816 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18208 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6303 _reflns_number_gt 3838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0657P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6303 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _refine_ls_shift/su_max 0.237 _refine_ls_shift/su_mean 0.016 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 C1B C 0.08082(7) 0.39837(7) 0.05227(7) 0.0423(4) Uani 1 1 d . . . C2B C 0.13670(8) 0.39185(7) 0.10869(7) 0.0438(4) Uani 1 1 d . . . C3B C 0.21038(7) 0.37355(7) 0.09506(7) 0.0419(4) Uani 1 1 d . . . C4B C 0.22862(7) 0.36734(6) 0.02635(7) 0.0410(4) Uani 1 1 d . . . C5B C 0.17158(7) 0.36984(7) -0.02965(7) 0.0436(4) Uani 1 1 d . . . C6B C 0.09677(7) 0.37841(7) -0.01482(7) 0.0437(4) Uani 1 1 d . . . C7B C 0.02439(8) 0.37559(7) -0.06059(8) 0.0506(4) Uani 1 1 d . . . C8B C -0.00030(9) 0.34484(9) -0.12169(9) 0.0676(5) Uani 1 1 d . . . C9B C -0.07670(10) 0.35575(10) -0.15028(10) 0.0861(6) Uani 1 1 d . . . H9BA H -0.0935 0.3371 -0.1927 0.103 Uiso 1 1 calc R . . C10B C -0.12629(10) 0.39173(10) -0.11924(11) 0.0828(6) Uani 1 1 d . . . H10A H -0.1745 0.3996 -0.1418 0.099 Uiso 1 1 calc R . . C11B C -0.10468(8) 0.41732(8) -0.05257(10) 0.0628(5) Uani 1 1 d . . . C12B C -0.15108(9) 0.45074(9) -0.01099(11) 0.0701(5) Uani 1 1 d . . . H12A H -0.2009 0.4607 -0.0278 0.084 Uiso 1 1 calc R . . C13B C -0.12239(9) 0.46825(8) 0.05390(10) 0.0647(5) Uani 1 1 d . . . H13A H -0.1541 0.4906 0.0803 0.078 Uiso 1 1 calc R . . C14B C -0.04721(8) 0.45496(7) 0.08474(8) 0.0545(4) Uani 1 1 d . . . C15B C -0.00015(7) 0.42173(7) 0.04496(8) 0.0455(4) Uani 1 1 d . . . C16B C -0.02992(8) 0.40620(7) -0.02387(8) 0.0508(4) Uani 1 1 d . . . C17B C -0.02633(11) 0.48200(10) 0.15616(9) 0.0838(6) Uani 1 1 d . . . H17A H 0.0243 0.4988 0.1593 0.126 Uiso 1 1 calc R . . H17B H -0.0286 0.4496 0.1904 0.126 Uiso 1 1 calc R . . H17C H -0.0613 0.5149 0.1644 0.126 Uiso 1 1 calc R . . C18B C 0.04559(10) 0.29621(10) -0.15620(10) 0.0897(7) Uani 1 1 d . . . H18A H 0.0823 0.2776 -0.1220 0.134 Uiso 1 1 calc R . . H18B H 0.0713 0.3160 -0.1916 0.134 Uiso 1 1 calc R . . H18C H 0.0122 0.2642 -0.1769 0.134 Uiso 1 1 calc R . . C19B C 0.19231(9) 0.37091(8) -0.10338(8) 0.0594(4) Uani 1 1 d . . . H19A H 0.1524 0.3909 -0.1331 0.089 Uiso 1 1 calc R . . H19B H 0.1988 0.3287 -0.1190 0.089 Uiso 1 1 calc R . . H19C H 0.2388 0.3938 -0.1048 0.089 Uiso 1 1 calc R . . C20B C 0.12111(9) 0.40047(9) 0.18322(8) 0.0670(5) Uani 1 1 d . . . H20A H 0.0708 0.3858 0.1886 0.100 Uiso 1 1 calc R . . H20B H 0.1251 0.4442 0.1952 0.100 Uiso 1 1 calc R . . H20C H 0.1575 0.3769 0.2132 0.100 Uiso 1 1 calc R . . C1A C 0.35207(8) 0.56923(8) 0.06945(9) 0.0566(4) Uani 1 1 d . . . C2A C 0.35887(8) 0.51248(8) 0.03394(8) 0.0534(4) Uani 1 1 d . . . C3A C 0.35455(7) 0.45628(7) 0.07196(8) 0.0497(4) Uani 1 1 d . . . C4A C 0.34002(8) 0.45746(8) 0.14142(8) 0.0527(4) Uani 1 1 d . . . C5A C 0.33808(8) 0.51415(9) 0.17840(9) 0.0589(4) Uani 1 1 d . . . C6A C 0.35258(8) 0.56950(8) 0.14324(10) 0.0600(5) Uani 1 1 d . . . C7A C 0.36702(9) 0.63533(10) 0.16752(12) 0.0737(6) Uani 1 1 d . . . C8A C 0.39093(10) 0.66377(11) 0.23121(14) 0.0916(7) Uani 1 1 d . . . C9A C 0.40129(13) 0.73050(15) 0.22964(19) 0.1203(11) Uani 1 1 d . . . H9AA H 0.4154 0.7508 0.2716 0.144 Uiso 1 1 calc R . . C10A C 0.39204(14) 0.76590(14) 0.1714(2) 0.1255(12) Uani 1 1 d . . . H10B H 0.3985 0.8092 0.1743 0.151 Uiso 1 1 calc R . . C11A C 0.37264(11) 0.73720(12) 0.10666(19) 0.0974(8) Uani 1 1 d . . . C12A C 0.36258(12) 0.76728(12) 0.0413(2) 0.1147(10) Uani 1 1 d . . . H12B H 0.3713 0.8102 0.0382 0.138 Uiso 1 1 calc R . . C13A C 0.34011(11) 0.73356(12) -0.01728(17) 0.1043(8) Uani 1 1 d . . . H13B H 0.3305 0.7551 -0.0591 0.125 Uiso 1 1 calc R . . C14A C 0.33052(9) 0.66673(10) -0.01781(13) 0.0785(6) Uani 1 1 d . . . C15A C 0.34874(9) 0.63562(9) 0.04505(11) 0.0679(5) Uani 1 1 d . . . C16A C 0.36274(9) 0.67249(10) 0.10626(13) 0.0751(6) Uani 1 1 d . . . C17A C 0.29621(12) 0.63761(11) -0.08463(12) 0.1005(7) Uani 1 1 d . . . H17D H 0.2675 0.6011 -0.0746 0.151 Uiso 1 1 calc R . . H17E H 0.3359 0.6257 -0.1120 0.151 Uiso 1 1 calc R . . H17F H 0.2632 0.6674 -0.1100 0.151 Uiso 1 1 calc R . . C18A C 0.41313(13) 0.63041(13) 0.29905(13) 0.1170(9) Uani 1 1 d . . . H18D H 0.4311 0.5890 0.2900 0.175 Uiso 1 1 calc R . . H18E H 0.3698 0.6274 0.3246 0.175 Uiso 1 1 calc R . . H18F H 0.4527 0.6535 0.3258 0.175 Uiso 1 1 calc R . . C19A C 0.31216(10) 0.51436(9) 0.25045(9) 0.0807(6) Uani 1 1 d . . . H19D H 0.2931 0.5552 0.2603 0.121 Uiso 1 1 calc R . . H19E H 0.3543 0.5042 0.2842 0.121 Uiso 1 1 calc R . . H19F H 0.2726 0.4838 0.2526 0.121 Uiso 1 1 calc R . . C20A C 0.37424(10) 0.50905(8) -0.04090(9) 0.0724(5) Uani 1 1 d . . . H20D H 0.3931 0.5488 -0.0549 0.109 Uiso 1 1 calc R . . H20E H 0.3280 0.4991 -0.0695 0.109 Uiso 1 1 calc R . . H20F H 0.4114 0.4771 -0.0461 0.109 Uiso 1 1 calc R . . C1 C 0.36841(8) 0.39453(7) 0.03847(8) 0.0494(4) Uani 1 1 d . . . C2 C 0.44272(8) 0.37752(9) 0.02951(9) 0.0680(5) Uani 1 1 d . . . H2A H 0.4824 0.4040 0.0462 0.082 Uiso 1 1 calc R . . C3 C 0.45903(9) 0.32261(9) -0.00335(10) 0.0718(5) Uani 1 1 d . . . H3A H 0.5091 0.3122 -0.0084 0.086 Uiso 1 1 calc R . . C4 C 0.40100(9) 0.28322(8) -0.02861(9) 0.0631(5) Uani 1 1 d . . . H4A H 0.4115 0.2463 -0.0515 0.076 Uiso 1 1 calc R . . C5 C 0.32719(8) 0.29877(7) -0.01978(8) 0.0513(4) Uani 1 1 d . . . H5A H 0.2881 0.2720 -0.0372 0.062 Uiso 1 1 calc R . . C6 C 0.30934(7) 0.35366(7) 0.01461(7) 0.0435(4) Uani 1 1 d . . . C7 C 0.26876(8) 0.35673(7) 0.15384(7) 0.0481(4) Uani 1 1 d . . . C8 C 0.26161(9) 0.29937(8) 0.18759(8) 0.0601(5) Uani 1 1 d . . . H8A H 0.2212 0.2730 0.1727 0.072 Uiso 1 1 calc R . . C9 C 0.31288(12) 0.28109(10) 0.24218(10) 0.0785(6) Uani 1 1 d . . . H9A H 0.3065 0.2431 0.2645 0.094 Uiso 1 1 calc R . . C10 C 0.37353(13) 0.31895(12) 0.26384(10) 0.0855(7) Uani 1 1 d . . . H10C H 0.4089 0.3063 0.3003 0.103 Uiso 1 1 calc R . . C11 C 0.38215(10) 0.37591(10) 0.23154(9) 0.0736(5) Uani 1 1 d . . . H11A H 0.4235 0.4013 0.2465 0.088 Uiso 1 1 calc R . . C12 C 0.32985(8) 0.39605(8) 0.17670(8) 0.0545(4) 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 C1B 0.0381(7) 0.0385(9) 0.0511(9) 0.0002(7) 0.0089(7) -0.0020(6) C2B 0.0431(8) 0.0418(9) 0.0476(9) 0.0005(7) 0.0102(7) 0.0000(6) C3B 0.0403(8) 0.0375(9) 0.0483(9) 0.0022(7) 0.0063(7) -0.0002(6) C4B 0.0376(7) 0.0352(9) 0.0505(9) -0.0013(7) 0.0069(7) -0.0015(6) C5B 0.0421(8) 0.0402(9) 0.0492(9) -0.0065(7) 0.0076(7) -0.0004(6) C6B 0.0398(8) 0.0410(9) 0.0500(9) -0.0027(7) 0.0033(7) -0.0008(6) C7B 0.0415(8) 0.0529(10) 0.0569(10) -0.0063(8) 0.0027(7) -0.0035(7) C8B 0.0529(10) 0.0776(14) 0.0700(12) -0.0194(10) -0.0036(9) -0.0075(9) C9B 0.0575(11) 0.1086(18) 0.0875(14) -0.0305(13) -0.0131(10) -0.0056(11) C10B 0.0468(10) 0.1001(17) 0.0960(15) -0.0117(12) -0.0166(10) -0.0018(10) C11B 0.0389(9) 0.0646(12) 0.0840(13) -0.0021(10) 0.0024(9) -0.0042(8) C12B 0.0390(9) 0.0688(13) 0.1020(15) 0.0077(11) 0.0060(10) 0.0038(8) C13B 0.0459(9) 0.0604(12) 0.0912(14) 0.0068(10) 0.0219(9) 0.0094(8) C14B 0.0511(9) 0.0498(10) 0.0651(11) 0.0084(8) 0.0178(8) 0.0062(8) C15B 0.0385(8) 0.0403(9) 0.0586(10) 0.0056(7) 0.0098(7) -0.0023(6) C16B 0.0385(8) 0.0481(10) 0.0652(11) 0.0002(8) 0.0030(8) -0.0047(7) C17B 0.0852(13) 0.0963(16) 0.0720(13) -0.0053(11) 0.0186(10) 0.0416(11) C18B 0.0734(12) 0.0992(17) 0.0930(15) -0.0468(13) -0.0057(11) -0.0013(11) C19B 0.0511(9) 0.0740(12) 0.0534(10) -0.0096(9) 0.0069(8) 0.0037(8) C20B 0.0579(10) 0.0887(14) 0.0554(10) 0.0040(9) 0.0112(8) 0.0190(9) C1A 0.0388(8) 0.0504(12) 0.0810(12) -0.0070(9) 0.0083(8) -0.0054(7) C2A 0.0390(8) 0.0546(12) 0.0668(11) -0.0071(9) 0.0061(7) -0.0080(7) C3A 0.0345(8) 0.0515(11) 0.0623(10) -0.0072(8) 0.0018(7) -0.0057(7) C4A 0.0385(8) 0.0582(12) 0.0599(11) -0.0079(9) -0.0008(7) -0.0022(7) C5A 0.0441(9) 0.0666(13) 0.0652(11) -0.0149(10) 0.0023(8) -0.0055(8) C6A 0.0392(8) 0.0621(13) 0.0788(13) -0.0219(10) 0.0075(8) -0.0047(8) C7A 0.0425(9) 0.0680(14) 0.1123(16) -0.0375(13) 0.0165(10) -0.0065(9) C8A 0.0531(11) 0.0955(19) 0.129(2) -0.0592(16) 0.0220(12) -0.0103(11) C9A 0.0697(15) 0.100(2) 0.195(3) -0.088(2) 0.0339(19) -0.0145(15) C10A 0.0715(15) 0.068(2) 0.242(4) -0.062(2) 0.039(2) -0.0096(13) C11A 0.0535(11) 0.0581(16) 0.185(3) -0.0266(18) 0.0315(15) -0.0003(10) C12A 0.0633(14) 0.0563(17) 0.232(4) 0.001(2) 0.0500(19) 0.0039(12) C13A 0.0608(13) 0.0703(18) 0.189(3) 0.0330(17) 0.0471(16) 0.0137(11) C14A 0.0477(10) 0.0647(15) 0.1278(19) 0.0176(14) 0.0301(11) 0.0047(9) C15A 0.0402(9) 0.0540(12) 0.1117(16) -0.0034(12) 0.0190(10) -0.0030(8) C16A 0.0421(9) 0.0539(13) 0.1318(19) -0.0185(13) 0.0207(11) -0.0027(8) C17A 0.0890(15) 0.1084(19) 0.1091(18) 0.0369(15) 0.0330(14) 0.0192(13) C18A 0.0895(16) 0.152(3) 0.110(2) -0.0668(19) 0.0126(14) -0.0330(15) C19A 0.0814(13) 0.0904(16) 0.0711(13) -0.0193(11) 0.0121(10) -0.0020(11) C20A 0.0787(12) 0.0646(13) 0.0759(13) -0.0025(10) 0.0169(10) -0.0096(10) C1 0.0395(8) 0.0522(11) 0.0568(10) -0.0008(8) 0.0067(7) 0.0012(7) C2 0.0385(9) 0.0698(13) 0.0962(14) -0.0074(10) 0.0096(9) -0.0022(8) C3 0.0442(9) 0.0687(13) 0.1057(15) -0.0020(11) 0.0225(9) 0.0119(9) C4 0.0597(11) 0.0493(11) 0.0845(13) -0.0009(9) 0.0260(9) 0.0095(8) C5 0.0489(9) 0.0425(10) 0.0645(10) -0.0016(8) 0.0152(8) -0.0008(7) C6 0.0394(8) 0.0427(10) 0.0493(9) 0.0019(7) 0.0085(7) 0.0014(7) C7 0.0439(8) 0.0538(11) 0.0478(9) 0.0027(8) 0.0097(7) 0.0096(7) C8 0.0655(10) 0.0575(12) 0.0593(11) 0.0105(9) 0.0157(9) 0.0137(8) C9 0.0948(15) 0.0763(15) 0.0656(13) 0.0154(11) 0.0134(12) 0.0330(12) C10 0.0872(15) 0.1053(19) 0.0609(12) 0.0082(13) -0.0062(11) 0.0506(14) C11 0.0568(10) 0.0948(17) 0.0657(12) -0.0068(11) -0.0088(9) 0.0185(10) C12 0.0458(9) 0.0652(12) 0.0518(10) -0.0019(8) 0.0017(8) 0.0092(8) _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 C1B C2B 1.3971(19) . ? C1B C6B 1.4238(19) . ? C1B C15B 1.5092(18) . ? C2B C3B 1.4139(18) . ? C2B C20B 1.509(2) . ? C3B C4B 1.4089(18) . ? C3B C7 1.4938(19) . ? C4B C5B 1.3985(19) . ? C4B C6 1.5001(18) . ? C5B C6B 1.3980(18) . ? C5B C19B 1.5122(19) . ? C6B C7B 1.476(2) . ? C7B C8B 1.380(2) . ? C7B C16B 1.416(2) . ? C8B C9B 1.423(2) . ? C8B C18B 1.516(2) . ? C9B C10B 1.355(3) . ? C10B C11B 1.414(2) . ? C11B C16B 1.398(2) . ? C11B C12B 1.405(2) . ? C12B C13B 1.354(2) . ? C13B C14B 1.426(2) . ? C14B C15B 1.389(2) . ? C14B C17B 1.505(2) . ? C15B C16B 1.417(2) . ? C1A C2A 1.402(2) . ? C1A C6A 1.427(2) . ? C1A C15A 1.489(2) . ? C2A C3A 1.411(2) . ? C2A C20A 1.505(2) . ? C3A C4A 1.397(2) . ? C3A C1 1.498(2) . ? C4A C5A 1.405(2) . ? C4A C12 1.495(2) . ? C5A C6A 1.399(2) . ? C5A C19A 1.515(2) . ? C6A C7A 1.491(2) . ? C7A C8A 1.397(3) . ? C7A C16A 1.420(3) . ? C8A C9A 1.433(4) . ? C8A C18A 1.506(3) . ? C9A C10A 1.351(4) . ? C10A C11A 1.403(4) . ? C11A C16A 1.389(3) . ? C11A C12A 1.411(3) . ? C12A C13A 1.364(4) . ? C13A C14A 1.433(3) . ? C14A C15A 1.391(3) . ? C14A C17A 1.501(3) . ? C15A C16A 1.420(3) . ? C1 C2 1.394(2) . ? C1 C6 1.399(2) . ? C2 C3 1.376(2) . ? C3 C4 1.374(2) . ? C4 C5 1.3769(19) . ? C5 C6 1.3981(19) . ? C7 C8 1.397(2) . ? C7 C12 1.400(2) . ? C8 C9 1.371(2) . ? C9 C10 1.371(3) . ? C10 C11 1.380(3) . ? C11 C12 1.397(2) . ? 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 C2B C1B C6B 119.25(12) . . ? C2B C1B C15B 133.58(13) . . ? C6B C1B C15B 107.14(12) . . ? C1B C2B C3B 118.03(12) . . ? C1B C2B C20B 123.13(12) . . ? C3B C2B C20B 118.78(13) . . ? C4B C3B C2B 120.95(13) . . ? C4B C3B C7 119.00(12) . . ? C2B C3B C7 119.94(12) . . ? C5B C4B C3B 120.45(12) . . ? C5B C4B C6 120.56(12) . . ? C3B C4B C6 118.86(12) . . ? C6B C5B C4B 117.73(12) . . ? C6B C5B C19B 121.73(13) . . ? C4B C5B C19B 120.14(12) . . ? C5B C6B C1B 120.93(13) . . ? C5B C6B C7B 130.60(13) . . ? C1B C6B C7B 108.24(12) . . ? C8B C7B C16B 118.68(13) . . ? C8B C7B C6B 134.87(14) . . ? C16B C7B C6B 105.83(12) . . ? C7B C8B C9B 116.97(16) . . ? C7B C8B C18B 124.55(15) . . ? C9B C8B C18B 118.22(16) . . ? C10B C9B C8B 123.69(18) . . ? C9B C10B C11B 119.95(16) . . ? C16B C11B C12B 116.48(16) . . ? C16B C11B C10B 116.51(16) . . ? C12B C11B C10B 126.96(16) . . ? C13B C12B C11B 119.17(15) . . ? C12B C13B C14B 124.81(16) . . ? C15B C14B C13B 117.29(15) . . ? C15B C14B C17B 127.04(14) . . ? C13B C14B C17B 115.58(14) . . ? C14B C15B C16B 117.16(13) . . ? C14B C15B C1B 137.52(14) . . ? C16B C15B C1B 105.21(12) . . ? C11B C16B C7B 122.97(15) . . ? C11B C16B C15B 124.88(15) . . ? C7B C16B C15B 112.12(13) . . ? C2A C1A C6A 120.18(16) . . ? C2A C1A C15A 131.68(17) . . ? C6A C1A C15A 108.01(15) . . ? C1A C2A C3A 117.56(15) . . ? C1A C2A C20A 123.25(15) . . ? C3A C2A C20A 119.12(14) . . ? C4A C3A C2A 120.87(14) . . ? C4A C3A C1 119.25(14) . . ? C2A C3A C1 119.84(14) . . ? C3A C4A C5A 121.54(15) . . ? C3A C4A C12 117.92(14) . . ? C5A C4A C12 120.49(15) . . ? C6A C5A C4A 117.36(15) . . ? C6A C5A C19A 122.39(15) . . ? C4A C5A C19A 119.87(16) . . ? C5A C6A C1A 120.15(15) . . ? C5A C6A C7A 132.28(18) . . ? C1A C6A C7A 107.53(17) . . ? C8A C7A C16A 118.6(2) . . ? C8A C7A C6A 135.3(2) . . ? C16A C7A C6A 105.60(17) . . ? C7A C8A C9A 116.0(3) . . ? C7A C8A C18A 126.1(2) . . ? C9A C8A C18A 117.7(2) . . ? C10A C9A C8A 124.5(3) . . ? C9A C10A C11A 119.9(3) . . ? C16A C11A C10A 117.1(3) . . ? C16A C11A C12A 116.2(3) . . ? C10A C11A C12A 126.7(3) . . ? C13A C12A C11A 120.2(3) . . ? C12A C13A C14A 123.5(3) . . ? C15A C14A C13A 116.8(2) . . ? C15A C14A C17A 126.13(19) . . ? C13A C14A C17A 116.9(2) . . ? C14A C15A C16A 117.9(2) . . ? C14A C15A C1A 136.57(19) . . ? C16A C15A C1A 105.24(18) . . ? C11A C16A C15A 124.3(3) . . ? C11A C16A C7A 123.6(2) . . ? C15A C16A C7A 112.13(18) . . ? C2 C1 C6 118.62(14) . . ? C2 C1 C3A 118.94(13) . . ? C6 C1 C3A 122.44(12) . . ? C3 C2 C1 121.81(16) . . ? C2 C3 C4 119.74(15) . . ? C5 C4 C3 119.46(16) . . ? C4 C5 C6 121.85(15) . . ? C1 C6 C5 118.47(13) . . ? C1 C6 C4B 121.28(13) . . ? C5 C6 C4B 120.24(13) . . ? C8 C7 C12 118.78(14) . . ? C8 C7 C3B 118.33(14) . . ? C12 C7 C3B 122.88(14) . . ? C9 C8 C7 121.46(18) . . ? C8 C9 C10 119.89(19) . . ? C9 C10 C11 120.00(18) . . ? C10 C11 C12 121.11(19) . . ? C11 C12 C7 118.74(16) . . ? C11 C12 C4A 120.82(16) . . ? C7 C12 C4A 120.41(13) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.126 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.029