# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address A.Krueger ; Institut fuer Anorganische Chemie Universitaet Wuerzburg Am Hubland D-97074 Wuerzburg, Germany ; Y.Kirchwehm ; Institut fuer Organische Chemie Universitaet Wuerzburg Am Hubland D-97074 Wuerzburg, Germany ; A.Damme ; Institut fuer Organische Chemie Universitaet Wuerzburg Am Hubland D-97074 Wuerzburg, Germany ; T.Kupfer ; Institut fuer Anorganische Chemie Universitaet Wuerzburg Am Hubland D-97074 Wuerzburg, Germany ; H.Braunschweig ; Institut fuer Anorganische Chemie Universitaet Wuerzburg Am Hubland D-97074 Wuerzburg, Germany ; _publ_contact_author_address ; Institut fuer Anorganische Chemie Universitaet Wuerzburg Am Hubland 97074 Wuerzburg, Germany ; _publ_contact_author_email H.Braunschweig@mail.uni-wuerzburg.de _publ_contact_author_fax +49-931-3184623 _publ_contact_author_phone +49-931-3185260 # 1. Submission Details _publ_contact_author_name 'Prof. Dr. Holger Braunschweig' _publ_contact_letter ; ? ; _publ_requested_category 'Organic Chemistry' _publ_requested_coeditor_name ? _publ_section_title ;Ortho-methylated tribenzotriquinacenes - paving the way to curved carbon networks ; data_1 _database_code_depnum_ccdc_archive 'CCDC 837041' _publ_section_abstract ;The synthesis of sterically crowded tribenzotriquinacenes with complete and partial substitution of the ortho-positions has been achieved using a double dehydration as the cyclization step. Ortho-methylation leads to a twisting of the tribenzotriquinacene structure and opens the way for further functionalization, eventually leading to curved model compounds for defective carbon networks. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C25 H22' _chemical_formula_sum 'C25 H22' _chemical_formula_weight 322.43 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6681(9) _cell_length_b 23.199(2) _cell_length_c 15.9130(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.037(4) _cell_angle_gamma 90.00 _cell_volume 3462.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7768 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6174 _exptl_absorpt_correction_T_max 0.6849 _exptl_absorpt_process_details 'Sadabs 2008/1 (Brucker 2008)' _exptl_special_details ; The crystal was immersed in a film of perfluoropolyether oil, mounted on a polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold nitrogen (Oxford Cryostream 700). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 265328 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.16 _reflns_number_total 6834 _reflns_number_gt 5678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 ver. 2010.3 (Bruker AXS)' _computing_cell_refinement 'Saint+ ver. 7.68A (Bruker AXS)' _computing_data_reduction 'Saint+ ver. 7.68A (Bruker AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0347P)^2^+2.8552P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6834 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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_1 C 0.1796(2) 0.67889(8) 0.76592(12) 0.0281(4) Uani 1 1 d . . . H1A_1 H 0.1364 0.7119 0.7884 0.042 Uiso 1 1 calc R . . H1B_1 H 0.1042 0.6540 0.7323 0.042 Uiso 1 1 calc R . . H1C_1 H 0.2397 0.6927 0.7286 0.042 Uiso 1 1 calc R . . C2_1 C 0.27020(18) 0.64480(7) 0.84127(11) 0.0210(4) Uani 1 1 d . . . C3_1 C 0.38868(18) 0.68374(7) 0.89901(11) 0.0203(4) Uani 1 1 d . . . H3_1 H 0.3753 0.7238 0.8752 0.024 Uiso 1 1 calc R . . C4_1 C 0.18255(18) 0.62034(8) 0.90329(12) 0.0225(4) Uani 1 1 d . . . H4_1 H 0.0775 0.6243 0.8787 0.027 Uiso 1 1 calc R . . C5_1 C 0.35113(18) 0.59340(7) 0.81127(11) 0.0204(4) Uani 1 1 d . . . H5_1 H 0.3091 0.5840 0.7490 0.024 Uiso 1 1 calc R . . C1_2 C 0.35632(18) 0.68456(7) 0.98703(12) 0.0210(4) Uani 1 1 d . . . C2_2 C 0.42540(19) 0.71522(8) 1.06043(12) 0.0262(4) Uani 1 1 d . . . H2_2 H 0.5102 0.7361 1.0611 0.031 Uiso 1 1 calc R . . C3_2 C 0.3686(2) 0.71495(8) 1.13286(13) 0.0295(4) Uani 1 1 d . . . H3_2 H 0.4159 0.7353 1.1835 0.035 Uiso 1 1 calc R . . C4_2 C 0.2439(2) 0.68534(8) 1.13180(13) 0.0303(4) Uani 1 1 d . . . H4_2 H 0.2049 0.6863 1.1811 0.036 Uiso 1 1 calc R . . C5_2 C 0.1752(2) 0.65417(8) 1.05865(13) 0.0271(4) Uani 1 1 d . . . H5_2 H 0.0900 0.6335 1.0580 0.033 Uiso 1 1 calc R . . C6_2 C 0.23285(18) 0.65370(8) 0.98685(12) 0.0225(4) Uani 1 1 d . . . C1_3 C 0.22793(18) 0.55799(8) 0.91596(11) 0.0212(4) Uani 1 1 d . . . C2_3 C 0.1832(2) 0.51911(8) 0.97041(12) 0.0263(4) Uani 1 1 d . . . H2_3 H 0.1124 0.5297 0.9998 0.032 Uiso 1 1 calc R . . C3_3 C 0.2436(2) 0.46478(8) 0.98104(12) 0.0281(4) Uani 1 1 d . . . H3_3 H 0.2147 0.4376 1.0181 0.034 Uiso 1 1 calc R . . C4_3 C 0.3465(2) 0.45005(8) 0.93761(11) 0.0240(4) Uani 1 1 d . . . H4_3 H 0.3884 0.4128 0.9464 0.029 Uiso 1 1 calc R . . C5_3 C 0.39075(18) 0.48817(8) 0.88134(11) 0.0214(4) Uani 1 1 d . . . C6_3 C 0.32833(18) 0.54338(7) 0.87046(11) 0.0190(4) Uani 1 1 d . . . C7_3 C 0.50052(19) 0.46868(8) 0.83576(13) 0.0265(4) Uani 1 1 d . . . H7A_3 H 0.4571 0.4654 0.7736 0.040 Uiso 1 1 calc R . . H7B_3 H 0.5381 0.4311 0.8585 0.040 Uiso 1 1 calc R . . H7C_3 H 0.5784 0.4968 0.8453 0.040 Uiso 1 1 calc R . . C1_4 C 0.52774(18) 0.66115(7) 0.88476(11) 0.0200(4) Uani 1 1 d . . . C2_4 C 0.66212(18) 0.68578(7) 0.91267(12) 0.0221(4) Uani 1 1 d . . . H2_4 H 0.6793 0.7152 0.9555 0.027 Uiso 1 1 calc R . . C3_4 C 0.77059(19) 0.66647(8) 0.87651(12) 0.0240(4) Uani 1 1 d . . . H3_4 H 0.8649 0.6805 0.8978 0.029 Uiso 1 1 calc R . . C4_4 C 0.7417(2) 0.62683(8) 0.80931(12) 0.0256(4) Uani 1 1 d . . . H4_4 H 0.8156 0.6164 0.7823 0.031 Uiso 1 1 calc R . . C5_4 C 0.60665(19) 0.60176(8) 0.78017(12) 0.0234(4) Uani 1 1 d . . . C6_4 C 0.50271(18) 0.61621(7) 0.82427(11) 0.0204(4) Uani 1 1 d . . . C7_4 C 0.5734(2) 0.56602(10) 0.69838(13) 0.0339(5) Uani 1 1 d . . . H7A_4 H 0.4717 0.5693 0.6700 0.051 Uiso 1 1 calc R . . H7B_4 H 0.5969 0.5256 0.7129 0.051 Uiso 1 1 calc R . . H7C_4 H 0.6300 0.5800 0.6591 0.051 Uiso 1 1 calc R . . C1_5 C 0.27500(19) 0.33199(8) 0.76188(12) 0.0233(4) Uani 1 1 d . . . H1A_5 H 0.2104 0.3235 0.7992 0.035 Uiso 1 1 calc R . . H1B_5 H 0.3525 0.3569 0.7930 0.035 Uiso 1 1 calc R . . H1C_5 H 0.3149 0.2959 0.7459 0.035 Uiso 1 1 calc R . . C2_5 C 0.19284(17) 0.36257(7) 0.68025(11) 0.0183(4) Uani 1 1 d . . . C3_5 C 0.11303(17) 0.41776(7) 0.70042(11) 0.0177(4) Uani 1 1 d . . . H3_5 H 0.1495 0.4298 0.7622 0.021 Uiso 1 1 calc R . . C4_5 C 0.28817(17) 0.38079(7) 0.61910(11) 0.0191(4) Uani 1 1 d . . . H4_5 H 0.3918 0.3753 0.6467 0.023 Uiso 1 1 calc R . . C5_5 C 0.07485(17) 0.32247(7) 0.62516(11) 0.0189(4) Uani 1 1 d . . . H5_5 H 0.0821 0.2840 0.6541 0.023 Uiso 1 1 calc R . . C1_6 C 0.23926(18) 0.34397(7) 0.53878(11) 0.0198(4) Uani 1 1 d . . . C2_6 C 0.2998(2) 0.33868(8) 0.46831(12) 0.0240(4) Uani 1 1 d . . . H2_6 H 0.3863 0.3580 0.4679 0.029 Uiso 1 1 calc R . . C3_6 C 0.2318(2) 0.30466(8) 0.39835(12) 0.0269(4) Uani 1 1 d . . . H3_6 H 0.2725 0.3006 0.3500 0.032 Uiso 1 1 calc R . . C4_6 C 0.1050(2) 0.27669(8) 0.39875(12) 0.0277(4) Uani 1 1 d . . . H4_6 H 0.0591 0.2539 0.3504 0.033 Uiso 1 1 calc R . . C5_6 C 0.04454(19) 0.28176(8) 0.46923(12) 0.0244(4) Uani 1 1 d . . . H5_6 H -0.0422 0.2626 0.4694 0.029 Uiso 1 1 calc R . . C6_6 C 0.11307(18) 0.31529(7) 0.53947(11) 0.0199(4) Uani 1 1 d . . . C1_7 C -0.06515(18) 0.34964(7) 0.63009(11) 0.0183(4) Uani 1 1 d . . . C2_7 C -0.20047(18) 0.32686(7) 0.59894(11) 0.0209(4) Uani 1 1 d . . . H2_7 H -0.2154 0.2947 0.5609 0.025 Uiso 1 1 calc R . . C3_7 C -0.31349(19) 0.35224(8) 0.62469(12) 0.0227(4) Uani 1 1 d . . . H3_7 H -0.4080 0.3390 0.6012 0.027 Uiso 1 1 calc R . . C4_7 C -0.28902(19) 0.39674(8) 0.68445(12) 0.0235(4) Uani 1 1 d . . . H4_7 H -0.3669 0.4119 0.7041 0.028 Uiso 1 1 calc R . . C5_7 C -0.15251(19) 0.42004(8) 0.71683(11) 0.0213(4) Uani 1 1 d . . . C6_7 C -0.04210(17) 0.39850(7) 0.68314(11) 0.0182(4) Uani 1 1 d . . . C7_7 C -0.1290(2) 0.46189(9) 0.79200(12) 0.0291(4) Uani 1 1 d . . . H7A_7 H -0.0266 0.4659 0.8177 0.044 Uiso 1 1 calc R . . H7B_7 H -0.1762 0.4473 0.8357 0.044 Uiso 1 1 calc R . . H7C_7 H -0.1691 0.4995 0.7712 0.044 Uiso 1 1 calc R . . C1_8 C 0.25196(18) 0.44340(7) 0.59870(11) 0.0202(4) Uani 1 1 d . . . C2_8 C 0.3068(2) 0.47770(8) 0.54305(12) 0.0257(4) Uani 1 1 d . . . H2_8 H 0.3789 0.4634 0.5174 0.031 Uiso 1 1 calc R . . C3_8 C 0.2544(2) 0.53311(8) 0.52564(12) 0.0285(4) Uani 1 1 d . . . H3_8 H 0.2904 0.5572 0.4877 0.034 Uiso 1 1 calc R . . C4_8 C 0.1497(2) 0.55320(8) 0.56355(12) 0.0260(4) Uani 1 1 d . . . H4_8 H 0.1140 0.5911 0.5503 0.031 Uiso 1 1 calc R . . C5_8 C 0.09428(18) 0.51975(7) 0.62080(11) 0.0214(4) Uani 1 1 d . . . C6_8 C 0.14809(17) 0.46353(7) 0.63862(11) 0.0187(4) Uani 1 1 d . . . C7_8 C -0.0189(2) 0.54470(8) 0.65938(13) 0.0275(4) Uani 1 1 d . . . H7A_8 H -0.1034 0.5199 0.6455 0.041 Uiso 1 1 calc R . . H7B_8 H -0.0443 0.5833 0.6355 0.041 Uiso 1 1 calc R . . H7C_8 H 0.0168 0.5473 0.7224 0.041 Uiso 1 1 calc 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_1 0.0271(10) 0.0240(9) 0.0264(10) 0.0066(8) -0.0068(8) 0.0002(8) C2_1 0.0192(8) 0.0187(9) 0.0212(9) 0.0020(7) -0.0025(7) -0.0016(7) C3_1 0.0183(8) 0.0168(8) 0.0225(9) 0.0010(7) -0.0012(7) -0.0008(7) C4_1 0.0164(8) 0.0240(9) 0.0244(10) 0.0010(7) -0.0004(7) -0.0016(7) C5_1 0.0205(9) 0.0212(9) 0.0163(9) 0.0000(7) -0.0017(7) -0.0017(7) C1_2 0.0174(8) 0.0187(9) 0.0240(9) 0.0004(7) -0.0008(7) 0.0057(7) C2_2 0.0201(9) 0.0251(10) 0.0291(10) -0.0029(8) -0.0025(8) 0.0054(7) C3_2 0.0266(10) 0.0306(10) 0.0261(10) -0.0057(8) -0.0037(8) 0.0118(8) C4_2 0.0335(11) 0.0305(10) 0.0266(10) 0.0018(8) 0.0067(8) 0.0144(8) C5_2 0.0241(9) 0.0259(10) 0.0316(11) 0.0023(8) 0.0071(8) 0.0060(8) C6_2 0.0199(9) 0.0199(9) 0.0247(10) 0.0020(7) -0.0003(7) 0.0053(7) C1_3 0.0189(8) 0.0219(9) 0.0194(9) -0.0017(7) -0.0018(7) -0.0052(7) C2_3 0.0296(10) 0.0262(10) 0.0233(10) -0.0051(8) 0.0068(8) -0.0076(8) C3_3 0.0401(11) 0.0243(10) 0.0184(9) 0.0012(7) 0.0043(8) -0.0109(8) C4_3 0.0321(10) 0.0169(9) 0.0180(9) -0.0002(7) -0.0036(8) -0.0024(7) C5_3 0.0193(9) 0.0215(9) 0.0186(9) -0.0020(7) -0.0042(7) -0.0044(7) C6_3 0.0178(8) 0.0196(9) 0.0153(8) -0.0009(7) -0.0046(7) -0.0055(7) C7_3 0.0234(9) 0.0232(9) 0.0308(11) -0.0028(8) 0.0023(8) -0.0007(7) C1_4 0.0217(9) 0.0168(8) 0.0195(9) 0.0041(7) 0.0012(7) -0.0004(7) C2_4 0.0226(9) 0.0172(9) 0.0244(9) -0.0004(7) 0.0015(7) -0.0025(7) C3_4 0.0186(9) 0.0229(9) 0.0284(10) 0.0033(7) 0.0016(7) -0.0047(7) C4_4 0.0250(9) 0.0278(10) 0.0254(10) 0.0033(8) 0.0090(8) -0.0010(8) C5_4 0.0256(9) 0.0246(9) 0.0190(9) 0.0017(7) 0.0037(7) -0.0026(7) C6_4 0.0217(9) 0.0185(8) 0.0180(9) 0.0038(7) -0.0011(7) -0.0022(7) C7_4 0.0371(11) 0.0419(12) 0.0233(10) -0.0047(9) 0.0085(9) -0.0059(9) C1_5 0.0212(9) 0.0226(9) 0.0226(9) 0.0051(7) -0.0016(7) -0.0002(7) C2_5 0.0157(8) 0.0187(8) 0.0179(9) 0.0016(7) -0.0010(7) -0.0002(6) C3_5 0.0164(8) 0.0180(8) 0.0164(8) 0.0003(6) -0.0004(7) -0.0015(6) C4_5 0.0148(8) 0.0222(9) 0.0185(9) 0.0004(7) 0.0003(7) -0.0012(7) C5_5 0.0172(8) 0.0138(8) 0.0225(9) 0.0011(7) -0.0010(7) -0.0008(6) C1_6 0.0201(8) 0.0176(8) 0.0186(9) 0.0022(7) -0.0013(7) 0.0055(7) C2_6 0.0263(9) 0.0216(9) 0.0229(9) 0.0029(7) 0.0033(8) 0.0062(7) C3_6 0.0341(10) 0.0275(10) 0.0172(9) 0.0015(7) 0.0024(8) 0.0140(8) C4_6 0.0292(10) 0.0243(10) 0.0222(10) -0.0049(7) -0.0081(8) 0.0114(8) C5_6 0.0193(9) 0.0211(9) 0.0276(10) -0.0040(7) -0.0045(7) 0.0060(7) C6_6 0.0196(8) 0.0152(8) 0.0216(9) 0.0002(7) -0.0012(7) 0.0056(7) C1_7 0.0175(8) 0.0179(8) 0.0181(9) 0.0034(7) 0.0015(7) -0.0002(6) C2_7 0.0215(9) 0.0177(8) 0.0215(9) 0.0006(7) 0.0018(7) -0.0039(7) C3_7 0.0174(8) 0.0245(9) 0.0242(10) 0.0039(7) 0.0012(7) -0.0055(7) C4_7 0.0198(9) 0.0274(10) 0.0243(10) 0.0005(7) 0.0075(7) -0.0007(7) C5_7 0.0232(9) 0.0217(9) 0.0190(9) 0.0014(7) 0.0050(7) -0.0026(7) C6_7 0.0180(8) 0.0183(8) 0.0158(8) 0.0032(6) -0.0009(7) -0.0026(6) C7_7 0.0279(10) 0.0343(11) 0.0260(10) -0.0071(8) 0.0081(8) -0.0039(8) C1_8 0.0192(8) 0.0212(9) 0.0166(9) -0.0013(7) -0.0027(7) -0.0053(7) C2_8 0.0274(10) 0.0275(10) 0.0217(9) -0.0023(7) 0.0048(8) -0.0078(8) C3_8 0.0383(11) 0.0250(10) 0.0201(10) 0.0021(7) 0.0027(8) -0.0117(8) C4_8 0.0337(10) 0.0169(9) 0.0213(9) 0.0022(7) -0.0053(8) -0.0045(7) C5_8 0.0198(9) 0.0192(9) 0.0195(9) -0.0011(7) -0.0062(7) -0.0033(7) C6_8 0.0172(8) 0.0190(8) 0.0157(8) -0.0002(7) -0.0044(7) -0.0055(7) C7_8 0.0255(10) 0.0200(9) 0.0329(11) -0.0006(8) -0.0008(8) 0.0004(7) _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_1 C2_1 1.524(2) . ? C1_1 H1A_1 0.9800 . ? C1_1 H1B_1 0.9800 . ? C1_1 H1C_1 0.9800 . ? C2_1 C4_1 1.556(2) . ? C2_1 C5_1 1.563(2) . ? C2_1 C3_1 1.569(2) . ? C3_1 C1_2 1.507(3) . ? C3_1 C1_4 1.511(2) . ? C3_1 H3_1 1.0000 . ? C4_1 C1_3 1.511(2) . ? C4_1 C6_2 1.513(3) . ? C4_1 H4_1 1.0000 . ? C5_1 C6_4 1.524(2) . ? C5_1 C6_3 1.544(2) . ? C5_1 H5_1 1.0000 . ? C1_2 C6_2 1.391(3) . ? C1_2 C2_2 1.392(3) . ? C2_2 C3_2 1.392(3) . ? C2_2 H2_2 0.9500 . ? C3_2 C4_2 1.385(3) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.394(3) . ? C4_2 H4_2 0.9500 . ? C5_2 C6_2 1.388(3) . ? C5_2 H5_2 0.9500 . ? C1_3 C6_3 1.387(3) . ? C1_3 C2_3 1.390(3) . ? C2_3 C3_3 1.382(3) . ? C2_3 H2_3 0.9500 . ? C3_3 C4_3 1.385(3) . ? C3_3 H3_3 0.9500 . ? C4_3 C5_3 1.397(3) . ? C4_3 H4_3 0.9500 . ? C5_3 C6_3 1.409(2) . ? C5_3 C7_3 1.493(3) . ? C7_3 H7A_3 0.9800 . ? C7_3 H7B_3 0.9800 . ? C7_3 H7C_3 0.9800 . ? C1_4 C2_4 1.390(2) . ? C1_4 C6_4 1.400(2) . ? C2_4 C3_4 1.387(3) . ? C2_4 H2_4 0.9500 . ? C3_4 C4_4 1.386(3) . ? C3_4 H3_4 0.9500 . ? C4_4 C5_4 1.402(3) . ? C4_4 H4_4 0.9500 . ? C5_4 C6_4 1.399(3) . ? C5_4 C7_4 1.511(3) . ? C7_4 H7A_4 0.9800 . ? C7_4 H7B_4 0.9800 . ? C7_4 H7C_4 0.9800 . ? C1_5 C2_5 1.523(2) . ? C1_5 H1A_5 0.9800 . ? C1_5 H1B_5 0.9800 . ? C1_5 H1C_5 0.9800 . ? C2_5 C4_5 1.553(2) . ? C2_5 C5_5 1.565(2) . ? C2_5 C3_5 1.568(2) . ? C3_5 C6_7 1.525(2) . ? C3_5 C6_8 1.540(2) . ? C3_5 H3_5 1.0000 . ? C4_5 C1_8 1.511(2) . ? C4_5 C1_6 1.515(2) . ? C4_5 H4_5 1.0000 . ? C5_5 C6_6 1.506(2) . ? C5_5 C1_7 1.512(2) . ? C5_5 H5_5 1.0000 . ? C1_6 C2_6 1.391(3) . ? C1_6 C6_6 1.392(2) . ? C2_6 C3_6 1.393(3) . ? C2_6 H2_6 0.9500 . ? C3_6 C4_6 1.389(3) . ? C3_6 H3_6 0.9500 . ? C4_6 C5_6 1.390(3) . ? C4_6 H4_6 0.9500 . ? C5_6 C6_6 1.391(2) . ? C5_6 H5_6 0.9500 . ? C1_7 C2_7 1.386(2) . ? C1_7 C6_7 1.399(2) . ? C2_7 C3_7 1.388(3) . ? C2_7 H2_7 0.9500 . ? C3_7 C4_7 1.384(3) . ? C3_7 H3_7 0.9500 . ? C4_7 C5_7 1.403(2) . ? C4_7 H4_7 0.9500 . ? C5_7 C6_7 1.398(2) . ? C5_7 C7_7 1.514(2) . ? C7_7 H7A_7 0.9800 . ? C7_7 H7B_7 0.9800 . ? C7_7 H7C_7 0.9800 . ? C1_8 C2_8 1.388(3) . ? C1_8 C6_8 1.393(2) . ? C2_8 C3_8 1.385(3) . ? C2_8 H2_8 0.9500 . ? C3_8 C4_8 1.378(3) . ? C3_8 H3_8 0.9500 . ? C4_8 C5_8 1.399(3) . ? C4_8 H4_8 0.9500 . ? C5_8 C6_8 1.407(2) . ? C5_8 C7_8 1.495(3) . ? C7_8 H7A_8 0.9800 . ? C7_8 H7B_8 0.9800 . ? C7_8 H7C_8 0.9800 . ? 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_1 C1_1 H1A_1 109.5 . . ? C2_1 C1_1 H1B_1 109.5 . . ? H1A_1 C1_1 H1B_1 109.5 . . ? C2_1 C1_1 H1C_1 109.5 . . ? H1A_1 C1_1 H1C_1 109.5 . . ? H1B_1 C1_1 H1C_1 109.5 . . ? C1_1 C2_1 C4_1 113.00(15) . . ? C1_1 C2_1 C5_1 112.99(15) . . ? C4_1 C2_1 C5_1 107.79(14) . . ? C1_1 C2_1 C3_1 111.15(14) . . ? C4_1 C2_1 C3_1 105.74(14) . . ? C5_1 C2_1 C3_1 105.64(13) . . ? C1_2 C3_1 C1_4 122.46(14) . . ? C1_2 C3_1 C2_1 105.35(14) . . ? C1_4 C3_1 C2_1 105.20(14) . . ? C1_2 C3_1 H3_1 107.7 . . ? C1_4 C3_1 H3_1 107.7 . . ? C2_1 C3_1 H3_1 107.7 . . ? C1_3 C4_1 C6_2 110.57(14) . . ? C1_3 C4_1 C2_1 104.40(14) . . ? C6_2 C4_1 C2_1 105.21(14) . . ? C1_3 C4_1 H4_1 112.1 . . ? C6_2 C4_1 H4_1 112.1 . . ? C2_1 C4_1 H4_1 112.1 . . ? C6_4 C5_1 C6_3 116.94(14) . . ? C6_4 C5_1 C2_1 103.29(14) . . ? C6_3 C5_1 C2_1 103.36(14) . . ? C6_4 C5_1 H5_1 110.9 . . ? C6_3 C5_1 H5_1 110.9 . . ? C2_1 C5_1 H5_1 110.9 . . ? C6_2 C1_2 C2_2 120.10(17) . . ? C6_2 C1_2 C3_1 111.28(15) . . ? C2_2 C1_2 C3_1 128.35(17) . . ? C3_2 C2_2 C1_2 119.15(18) . . ? C3_2 C2_2 H2_2 120.4 . . ? C1_2 C2_2 H2_2 120.4 . . ? C4_2 C3_2 C2_2 120.65(18) . . ? C4_2 C3_2 H3_2 119.7 . . ? C2_2 C3_2 H3_2 119.7 . . ? C3_2 C4_2 C5_2 120.30(19) . . ? C3_2 C4_2 H4_2 119.8 . . ? C5_2 C4_2 H4_2 119.8 . . ? C6_2 C5_2 C4_2 119.10(18) . . ? C6_2 C5_2 H5_2 120.5 . . ? C4_2 C5_2 H5_2 120.5 . . ? C5_2 C6_2 C1_2 120.68(17) . . ? C5_2 C6_2 C4_1 128.29(17) . . ? C1_2 C6_2 C4_1 110.97(16) . . ? C6_3 C1_3 C2_3 121.99(17) . . ? C6_3 C1_3 C4_1 112.45(15) . . ? C2_3 C1_3 C4_1 125.47(17) . . ? C3_3 C2_3 C1_3 118.80(18) . . ? C3_3 C2_3 H2_3 120.6 . . ? C1_3 C2_3 H2_3 120.6 . . ? C2_3 C3_3 C4_3 119.83(17) . . ? C2_3 C3_3 H3_3 120.1 . . ? C4_3 C3_3 H3_3 120.1 . . ? C3_3 C4_3 C5_3 122.15(17) . . ? C3_3 C4_3 H4_3 118.9 . . ? C5_3 C4_3 H4_3 118.9 . . ? C4_3 C5_3 C6_3 117.76(17) . . ? C4_3 C5_3 C7_3 118.92(16) . . ? C6_3 C5_3 C7_3 123.33(16) . . ? C1_3 C6_3 C5_3 119.44(16) . . ? C1_3 C6_3 C5_1 110.88(15) . . ? C5_3 C6_3 C5_1 129.66(16) . . ? C5_3 C7_3 H7A_3 109.5 . . ? C5_3 C7_3 H7B_3 109.5 . . ? H7A_3 C7_3 H7B_3 109.5 . . ? C5_3 C7_3 H7C_3 109.5 . . ? H7A_3 C7_3 H7C_3 109.5 . . ? H7B_3 C7_3 H7C_3 109.5 . . ? C2_4 C1_4 C6_4 121.22(17) . . ? C2_4 C1_4 C3_1 127.33(16) . . ? C6_4 C1_4 C3_1 110.49(15) . . ? C3_4 C2_4 C1_4 118.48(17) . . ? C3_4 C2_4 H2_4 120.8 . . ? C1_4 C2_4 H2_4 120.8 . . ? C4_4 C3_4 C2_4 120.21(16) . . ? C4_4 C3_4 H3_4 119.9 . . ? C2_4 C3_4 H3_4 119.9 . . ? C3_4 C4_4 C5_4 121.82(17) . . ? C3_4 C4_4 H4_4 119.1 . . ? C5_4 C4_4 H4_4 119.1 . . ? C6_4 C5_4 C4_4 117.37(17) . . ? C6_4 C5_4 C7_4 122.35(16) . . ? C4_4 C5_4 C7_4 119.95(17) . . ? C5_4 C6_4 C1_4 119.87(16) . . ? C5_4 C6_4 C5_1 129.26(16) . . ? C1_4 C6_4 C5_1 110.61(15) . . ? C5_4 C7_4 H7A_4 109.5 . . ? C5_4 C7_4 H7B_4 109.5 . . ? H7A_4 C7_4 H7B_4 109.5 . . ? C5_4 C7_4 H7C_4 109.5 . . ? H7A_4 C7_4 H7C_4 109.5 . . ? H7B_4 C7_4 H7C_4 109.5 . . ? C2_5 C1_5 H1A_5 109.5 . . ? C2_5 C1_5 H1B_5 109.5 . . ? H1A_5 C1_5 H1B_5 109.5 . . ? C2_5 C1_5 H1C_5 109.5 . . ? H1A_5 C1_5 H1C_5 109.5 . . ? H1B_5 C1_5 H1C_5 109.5 . . ? C1_5 C2_5 C4_5 113.28(14) . . ? C1_5 C2_5 C5_5 111.06(14) . . ? C4_5 C2_5 C5_5 105.88(13) . . ? C1_5 C2_5 C3_5 112.74(14) . . ? C4_5 C2_5 C3_5 107.60(13) . . ? C5_5 C2_5 C3_5 105.78(13) . . ? C6_7 C3_5 C6_8 116.49(14) . . ? C6_7 C3_5 C2_5 103.61(13) . . ? C6_8 C3_5 C2_5 103.71(13) . . ? C6_7 C3_5 H3_5 110.8 . . ? C6_8 C3_5 H3_5 110.8 . . ? C2_5 C3_5 H3_5 110.8 . . ? C1_8 C4_5 C1_6 110.63(14) . . ? C1_8 C4_5 C2_5 104.75(14) . . ? C1_6 C4_5 C2_5 105.31(13) . . ? C1_8 C4_5 H4_5 111.9 . . ? C1_6 C4_5 H4_5 111.9 . . ? C2_5 C4_5 H4_5 111.9 . . ? C6_6 C5_5 C1_7 120.82(14) . . ? C6_6 C5_5 C2_5 105.51(14) . . ? C1_7 C5_5 C2_5 105.26(13) . . ? C6_6 C5_5 H5_5 108.2 . . ? C1_7 C5_5 H5_5 108.2 . . ? C2_5 C5_5 H5_5 108.2 . . ? C2_6 C1_6 C6_6 120.37(17) . . ? C2_6 C1_6 C4_5 128.60(16) . . ? C6_6 C1_6 C4_5 110.96(15) . . ? C1_6 C2_6 C3_6 119.01(18) . . ? C1_6 C2_6 H2_6 120.5 . . ? C3_6 C2_6 H2_6 120.5 . . ? C4_6 C3_6 C2_6 120.49(18) . . ? C4_6 C3_6 H3_6 119.8 . . ? C2_6 C3_6 H3_6 119.8 . . ? C3_6 C4_6 C5_6 120.58(17) . . ? C3_6 C4_6 H4_6 119.7 . . ? C5_6 C4_6 H4_6 119.7 . . ? C4_6 C5_6 C6_6 118.97(18) . . ? C4_6 C5_6 H5_6 120.5 . . ? C6_6 C5_6 H5_6 120.5 . . ? C5_6 C6_6 C1_6 120.57(17) . . ? C5_6 C6_6 C5_5 128.02(16) . . ? C1_6 C6_6 C5_5 111.24(15) . . ? C2_7 C1_7 C6_7 121.55(16) . . ? C2_7 C1_7 C5_5 126.97(16) . . ? C6_7 C1_7 C5_5 110.83(14) . . ? C1_7 C2_7 C3_7 118.35(16) . . ? C1_7 C2_7 H2_7 120.8 . . ? C3_7 C2_7 H2_7 120.8 . . ? C4_7 C3_7 C2_7 120.24(16) . . ? C4_7 C3_7 H3_7 119.9 . . ? C2_7 C3_7 H3_7 119.9 . . ? C3_7 C4_7 C5_7 121.88(17) . . ? C3_7 C4_7 H4_7 119.1 . . ? C5_7 C4_7 H4_7 119.1 . . ? C6_7 C5_7 C4_7 117.33(16) . . ? C6_7 C5_7 C7_7 123.36(16) . . ? C4_7 C5_7 C7_7 118.98(16) . . ? C5_7 C6_7 C1_7 119.77(15) . . ? C5_7 C6_7 C3_5 129.45(15) . . ? C1_7 C6_7 C3_5 110.61(15) . . ? C5_7 C7_7 H7A_7 109.5 . . ? C5_7 C7_7 H7B_7 109.5 . . ? H7A_7 C7_7 H7B_7 109.5 . . ? C5_7 C7_7 H7C_7 109.5 . . ? H7A_7 C7_7 H7C_7 109.5 . . ? H7B_7 C7_7 H7C_7 109.5 . . ? C2_8 C1_8 C6_8 121.86(17) . . ? C2_8 C1_8 C4_5 125.73(17) . . ? C6_8 C1_8 C4_5 112.31(15) . . ? C3_8 C2_8 C1_8 118.83(18) . . ? C3_8 C2_8 H2_8 120.6 . . ? C1_8 C2_8 H2_8 120.6 . . ? C4_8 C3_8 C2_8 119.87(17) . . ? C4_8 C3_8 H3_8 120.1 . . ? C2_8 C3_8 H3_8 120.1 . . ? C3_8 C4_8 C5_8 122.37(17) . . ? C3_8 C4_8 H4_8 118.8 . . ? C5_8 C4_8 H4_8 118.8 . . ? C4_8 C5_8 C6_8 117.65(17) . . ? C4_8 C5_8 C7_8 119.15(16) . . ? C6_8 C5_8 C7_8 123.21(16) . . ? C1_8 C6_8 C5_8 119.41(16) . . ? C1_8 C6_8 C3_5 110.78(15) . . ? C5_8 C6_8 C3_5 129.79(16) . . ? C5_8 C7_8 H7A_8 109.5 . . ? C5_8 C7_8 H7B_8 109.5 . . ? H7A_8 C7_8 H7B_8 109.5 . . ? C5_8 C7_8 H7C_8 109.5 . . ? H7A_8 C7_8 H7C_8 109.5 . . ? H7B_8 C7_8 H7C_8 109.5 . . ? 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 C1_1 C2_1 C3_1 C1_2 117.82(16) . . . . ? C4_1 C2_1 C3_1 C1_2 -5.16(17) . . . . ? C5_1 C2_1 C3_1 C1_2 -119.27(14) . . . . ? C1_1 C2_1 C3_1 C1_4 -111.53(16) . . . . ? C4_1 C2_1 C3_1 C1_4 125.49(14) . . . . ? C5_1 C2_1 C3_1 C1_4 11.38(17) . . . . ? C1_1 C2_1 C4_1 C1_3 132.11(15) . . . . ? C5_1 C2_1 C4_1 C1_3 6.53(17) . . . . ? C3_1 C2_1 C4_1 C1_3 -106.09(15) . . . . ? C1_1 C2_1 C4_1 C6_2 -111.42(16) . . . . ? C5_1 C2_1 C4_1 C6_2 123.00(14) . . . . ? C3_1 C2_1 C4_1 C6_2 10.37(17) . . . . ? C1_1 C2_1 C5_1 C6_4 102.07(16) . . . . ? C4_1 C2_1 C5_1 C6_4 -132.34(14) . . . . ? C3_1 C2_1 C5_1 C6_4 -19.65(17) . . . . ? C1_1 C2_1 C5_1 C6_3 -135.62(15) . . . . ? C4_1 C2_1 C5_1 C6_3 -10.03(17) . . . . ? C3_1 C2_1 C5_1 C6_3 102.65(15) . . . . ? C1_4 C3_1 C1_2 C6_2 -122.36(17) . . . . ? C2_1 C3_1 C1_2 C6_2 -2.56(19) . . . . ? C1_4 C3_1 C1_2 C2_2 63.7(2) . . . . ? C2_1 C3_1 C1_2 C2_2 -176.50(17) . . . . ? C6_2 C1_2 C2_2 C3_2 -0.6(3) . . . . ? C3_1 C1_2 C2_2 C3_2 172.87(17) . . . . ? C1_2 C2_2 C3_2 C4_2 -0.9(3) . . . . ? C2_2 C3_2 C4_2 C5_2 1.5(3) . . . . ? C3_2 C4_2 C5_2 C6_2 -0.6(3) . . . . ? C4_2 C5_2 C6_2 C1_2 -1.0(3) . . . . ? C4_2 C5_2 C6_2 C4_1 175.90(17) . . . . ? C2_2 C1_2 C6_2 C5_2 1.6(3) . . . . ? C3_1 C1_2 C6_2 C5_2 -172.94(16) . . . . ? C2_2 C1_2 C6_2 C4_1 -175.80(15) . . . . ? C3_1 C1_2 C6_2 C4_1 9.7(2) . . . . ? C1_3 C4_1 C6_2 C5_2 -77.5(2) . . . . ? C2_1 C4_1 C6_2 C5_2 170.29(17) . . . . ? C1_3 C4_1 C6_2 C1_2 99.57(17) . . . . ? C2_1 C4_1 C6_2 C1_2 -12.60(19) . . . . ? C6_2 C4_1 C1_3 C6_3 -112.65(17) . . . . ? C2_1 C4_1 C1_3 C6_3 0.03(19) . . . . ? C6_2 C4_1 C1_3 C2_3 63.7(2) . . . . ? C2_1 C4_1 C1_3 C2_3 176.43(17) . . . . ? C6_3 C1_3 C2_3 C3_3 1.7(3) . . . . ? C4_1 C1_3 C2_3 C3_3 -174.37(17) . . . . ? C1_3 C2_3 C3_3 C4_3 -0.1(3) . . . . ? C2_3 C3_3 C4_3 C5_3 -1.2(3) . . . . ? C3_3 C4_3 C5_3 C6_3 0.9(3) . . . . ? C3_3 C4_3 C5_3 C7_3 -178.97(16) . . . . ? C2_3 C1_3 C6_3 C5_3 -2.0(3) . . . . ? C4_1 C1_3 C6_3 C5_3 174.54(15) . . . . ? C2_3 C1_3 C6_3 C5_1 176.66(16) . . . . ? C4_1 C1_3 C6_3 C5_1 -6.8(2) . . . . ? C4_3 C5_3 C6_3 C1_3 0.7(2) . . . . ? C7_3 C5_3 C6_3 C1_3 -179.49(16) . . . . ? C4_3 C5_3 C6_3 C5_1 -177.68(16) . . . . ? C7_3 C5_3 C6_3 C5_1 2.1(3) . . . . ? C6_4 C5_1 C6_3 C1_3 123.08(16) . . . . ? C2_1 C5_1 C6_3 C1_3 10.40(18) . . . . ? C6_4 C5_1 C6_3 C5_3 -58.4(2) . . . . ? C2_1 C5_1 C6_3 C5_3 -171.11(16) . . . . ? C1_2 C3_1 C1_4 C2_4 -69.1(2) . . . . ? C2_1 C3_1 C1_4 C2_4 171.01(17) . . . . ? C1_2 C3_1 C1_4 C6_4 122.12(17) . . . . ? C2_1 C3_1 C1_4 C6_4 2.25(19) . . . . ? C6_4 C1_4 C2_4 C3_4 2.7(3) . . . . ? C3_1 C1_4 C2_4 C3_4 -165.01(17) . . . . ? C1_4 C2_4 C3_4 C4_4 5.0(3) . . . . ? C2_4 C3_4 C4_4 C5_4 -4.9(3) . . . . ? C3_4 C4_4 C5_4 C6_4 -2.9(3) . . . . ? C3_4 C4_4 C5_4 C7_4 170.58(18) . . . . ? C4_4 C5_4 C6_4 C1_4 10.5(3) . . . . ? C7_4 C5_4 C6_4 C1_4 -162.87(17) . . . . ? C4_4 C5_4 C6_4 C5_1 -175.94(17) . . . . ? C7_4 C5_4 C6_4 C5_1 10.7(3) . . . . ? C2_4 C1_4 C6_4 C5_4 -10.6(3) . . . . ? C3_1 C1_4 C6_4 C5_4 158.94(16) . . . . ? C2_4 C1_4 C6_4 C5_1 174.70(16) . . . . ? C3_1 C1_4 C6_4 C5_1 -15.74(19) . . . . ? C6_3 C5_1 C6_4 C5_4 95.4(2) . . . . ? C2_1 C5_1 C6_4 C5_4 -151.83(18) . . . . ? C6_3 C5_1 C6_4 C1_4 -90.50(18) . . . . ? C2_1 C5_1 C6_4 C1_4 22.21(18) . . . . ? C1_5 C2_5 C3_5 C6_7 -103.75(15) . . . . ? C4_5 C2_5 C3_5 C6_7 130.62(14) . . . . ? C5_5 C2_5 C3_5 C6_7 17.80(16) . . . . ? C1_5 C2_5 C3_5 C6_8 134.14(14) . . . . ? C4_5 C2_5 C3_5 C6_8 8.51(16) . . . . ? C5_5 C2_5 C3_5 C6_8 -104.31(14) . . . . ? C1_5 C2_5 C4_5 C1_8 -130.42(15) . . . . ? C5_5 C2_5 C4_5 C1_8 107.64(14) . . . . ? C3_5 C2_5 C4_5 C1_8 -5.12(17) . . . . ? C1_5 C2_5 C4_5 C1_6 112.85(16) . . . . ? C5_5 C2_5 C4_5 C1_6 -9.09(17) . . . . ? C3_5 C2_5 C4_5 C1_6 -121.85(14) . . . . ? C1_5 C2_5 C5_5 C6_6 -118.76(15) . . . . ? C4_5 C2_5 C5_5 C6_6 4.59(17) . . . . ? C3_5 C2_5 C5_5 C6_6 118.61(14) . . . . ? C1_5 C2_5 C5_5 C1_7 112.42(16) . . . . ? C4_5 C2_5 C5_5 C1_7 -124.22(14) . . . . ? C3_5 C2_5 C5_5 C1_7 -10.20(17) . . . . ? C1_8 C4_5 C1_6 C2_6 75.2(2) . . . . ? C2_5 C4_5 C1_6 C2_6 -172.18(16) . . . . ? C1_8 C4_5 C1_6 C6_6 -101.71(17) . . . . ? C2_5 C4_5 C1_6 C6_6 10.95(18) . . . . ? C6_6 C1_6 C2_6 C3_6 0.5(3) . . . . ? C4_5 C1_6 C2_6 C3_6 -176.14(16) . . . . ? C1_6 C2_6 C3_6 C4_6 0.3(3) . . . . ? C2_6 C3_6 C4_6 C5_6 -0.6(3) . . . . ? C3_6 C4_6 C5_6 C6_6 0.0(3) . . . . ? C4_6 C5_6 C6_6 C1_6 0.8(2) . . . . ? C4_6 C5_6 C6_6 C5_5 -173.91(16) . . . . ? C2_6 C1_6 C6_6 C5_6 -1.1(2) . . . . ? C4_5 C1_6 C6_6 C5_6 176.08(15) . . . . ? C2_6 C1_6 C6_6 C5_5 174.48(15) . . . . ? C4_5 C1_6 C6_6 C5_5 -8.35(19) . . . . ? C1_7 C5_5 C6_6 C5_6 -63.8(2) . . . . ? C2_5 C5_5 C6_6 C5_6 177.28(16) . . . . ? C1_7 C5_5 C6_6 C1_6 121.04(17) . . . . ? C2_5 C5_5 C6_6 C1_6 2.13(18) . . . . ? C6_6 C5_5 C1_7 C2_7 68.0(2) . . . . ? C2_5 C5_5 C1_7 C2_7 -172.91(16) . . . . ? C6_6 C5_5 C1_7 C6_7 -121.21(17) . . . . ? C2_5 C5_5 C1_7 C6_7 -2.17(18) . . . . ? C6_7 C1_7 C2_7 C3_7 -2.8(3) . . . . ? C5_5 C1_7 C2_7 C3_7 167.07(16) . . . . ? C1_7 C2_7 C3_7 C4_7 -4.2(3) . . . . ? C2_7 C3_7 C4_7 C5_7 4.0(3) . . . . ? C3_7 C4_7 C5_7 C6_7 3.1(3) . . . . ? C3_7 C4_7 C5_7 C7_7 -170.48(17) . . . . ? C4_7 C5_7 C6_7 C1_7 -9.9(2) . . . . ? C7_7 C5_7 C6_7 C1_7 163.40(17) . . . . ? C4_7 C5_7 C6_7 C3_5 175.30(17) . . . . ? C7_7 C5_7 C6_7 C3_5 -11.4(3) . . . . ? C2_7 C1_7 C6_7 C5_7 10.0(3) . . . . ? C5_5 C1_7 C6_7 C5_7 -161.33(15) . . . . ? C2_7 C1_7 C6_7 C3_5 -174.29(15) . . . . ? C5_5 C1_7 C6_7 C3_5 14.38(19) . . . . ? C6_8 C3_5 C6_7 C5_7 -91.8(2) . . . . ? C2_5 C3_5 C6_7 C5_7 155.04(17) . . . . ? C6_8 C3_5 C6_7 C1_7 93.01(18) . . . . ? C2_5 C3_5 C6_7 C1_7 -20.14(18) . . . . ? C1_6 C4_5 C1_8 C2_8 -64.1(2) . . . . ? C2_5 C4_5 C1_8 C2_8 -177.14(16) . . . . ? C1_6 C4_5 C1_8 C6_8 112.28(16) . . . . ? C2_5 C4_5 C1_8 C6_8 -0.73(18) . . . . ? C6_8 C1_8 C2_8 C3_8 -1.3(3) . . . . ? C4_5 C1_8 C2_8 C3_8 174.84(16) . . . . ? C1_8 C2_8 C3_8 C4_8 0.1(3) . . . . ? C2_8 C3_8 C4_8 C5_8 0.9(3) . . . . ? C3_8 C4_8 C5_8 C6_8 -0.6(3) . . . . ? C3_8 C4_8 C5_8 C7_8 179.88(17) . . . . ? C2_8 C1_8 C6_8 C5_8 1.5(2) . . . . ? C4_5 C1_8 C6_8 C5_8 -175.08(15) . . . . ? C2_8 C1_8 C6_8 C3_5 -176.93(16) . . . . ? C4_5 C1_8 C6_8 C3_5 6.50(19) . . . . ? C4_8 C5_8 C6_8 C1_8 -0.5(2) . . . . ? C7_8 C5_8 C6_8 C1_8 178.94(15) . . . . ? C4_8 C5_8 C6_8 C3_5 177.53(16) . . . . ? C7_8 C5_8 C6_8 C3_5 -3.0(3) . . . . ? C6_7 C3_5 C6_8 C1_8 -122.36(16) . . . . ? C2_5 C3_5 C6_8 C1_8 -9.26(17) . . . . ? C6_7 C3_5 C6_8 C5_8 59.4(2) . . . . ? C2_5 C3_5 C6_8 C5_8 172.53(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.298 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.045 data_2 _database_code_depnum_ccdc_archive 'CCDC 837042' _publ_section_abstract ;The synthesis of sterically crowded tribenzotriquinacenes with complete and partial substitution of the ortho-positions has been achieved using a double dehydration as the cyclization step. Ortho-methylation leads to a twisting of the tribenzotriquinacene structure and opens the way for further functionalization, eventually leading to curved model compounds for defective carbon networks. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C29 H30' _chemical_formula_sum 'C29 H30' _chemical_formula_weight 378.53 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.2086(9) _cell_length_b 13.1797(10) _cell_length_c 14.0845(10) _cell_angle_alpha 70.585(3) _cell_angle_beta 76.790(3) _cell_angle_gamma 87.887(3) _cell_volume 2079.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7590 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.90 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6308 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details 'Sadabs 2008/1 (Brucker 2008)' _exptl_special_details ; The crystal was immersed in a film of perfluoropolyether oil, mounted on a polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold nitrogen (Oxford Cryostream 700). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 85497 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.94 _reflns_number_total 8025 _reflns_number_gt 7343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 ver. 2008.3 (Bruker AXS)' _computing_cell_refinement 'Saint+ ver. 7.53A (Bruker AXS)' _computing_data_reduction 'Saint+ ver. 7.53A (Bruker AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^+0.7868P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8025 _refine_ls_number_parameters 537 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _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 0.01663(10) 0.55485(9) 0.15261(9) 0.0199(2) Uani 1 1 d . . . C2 C -0.03911(11) 0.61111(9) 0.07519(10) 0.0231(3) Uani 1 1 d . . . C3 C 0.02141(11) 0.63946(10) -0.02689(10) 0.0251(3) Uani 1 1 d . . . H3A H -0.0147 0.6766 -0.0809 0.030 Uiso 1 1 calc R . . C4 C 0.13307(11) 0.61469(10) -0.05154(10) 0.0246(3) Uani 1 1 d . . . H4A H 0.1725 0.6373 -0.1221 0.030 Uiso 1 1 calc R . . C5 C 0.18916(10) 0.55752(10) 0.02410(9) 0.0216(2) Uani 1 1 d . . . C6 C 0.12828(10) 0.52551(9) 0.12733(9) 0.0194(2) Uani 1 1 d . . . C7 C -0.04568(10) 0.61835(9) 0.30456(9) 0.0206(2) Uani 1 1 d . . . C8 C -0.14083(10) 0.67929(10) 0.31632(9) 0.0243(3) Uani 1 1 d . . . C9 C -0.12376(11) 0.78013(10) 0.32515(10) 0.0271(3) Uani 1 1 d . . . H9A H -0.1864 0.8237 0.3341 0.033 Uiso 1 1 calc R . . C10 C -0.01816(11) 0.81761(10) 0.32121(10) 0.0258(3) Uani 1 1 d . . . H10A H -0.0082 0.8897 0.3185 0.031 Uiso 1 1 calc R . . C11 C 0.07490(11) 0.75167(10) 0.32109(9) 0.0218(3) Uani 1 1 d . . . C12 C 0.05722(10) 0.64828(9) 0.31971(9) 0.0192(2) Uani 1 1 d . . . C13 C 0.24961(10) 0.53526(9) 0.31797(9) 0.0183(2) Uani 1 1 d . . . C14 C 0.33364(10) 0.55620(9) 0.36273(9) 0.0206(2) Uani 1 1 d . . . C15 C 0.44249(10) 0.52559(10) 0.32855(9) 0.0237(3) Uani 1 1 d . . . H15A H 0.5028 0.5455 0.3520 0.028 Uiso 1 1 calc R . . C16 C 0.46447(10) 0.46720(10) 0.26169(9) 0.0231(3) Uani 1 1 d . . . H16A H 0.5394 0.4473 0.2407 0.028 Uiso 1 1 calc R . . C17 C 0.37876(10) 0.43646(9) 0.22402(9) 0.0204(2) Uani 1 1 d . . . C18 C 0.27230(10) 0.47672(9) 0.24867(9) 0.0182(2) Uani 1 1 d . . . C19 C -0.02979(10) 0.51962(9) 0.27003(9) 0.0199(2) Uani 1 1 d . . . H19A H -0.0993 0.4717 0.2940 0.024 Uiso 1 1 calc R . . C20 C 0.12371(10) 0.54580(9) 0.35154(9) 0.0183(2) Uani 1 1 d . . . H20A H 0.1042 0.5172 0.4289 0.022 Uiso 1 1 calc R . . C21 C 0.16394(10) 0.45145(9) 0.22353(9) 0.0182(2) Uani 1 1 d . . . H21A H 0.1630 0.3754 0.2241 0.022 Uiso 1 1 calc R . . C22 C 0.07049(10) 0.46318(9) 0.31465(9) 0.0184(2) Uani 1 1 d . . . C23 C 0.03781(10) 0.35614(9) 0.40173(9) 0.0219(2) Uani 1 1 d . . . H23A H 0.0090 0.3050 0.3753 0.033 Uiso 1 1 calc R . . H23B H -0.0207 0.3672 0.4575 0.033 Uiso 1 1 calc R . . H23C H 0.1041 0.3274 0.4284 0.033 Uiso 1 1 calc R . . C24 C -0.16033(11) 0.64073(11) 0.09676(11) 0.0296(3) Uani 1 1 d . . . H24A H -0.1864 0.6639 0.0323 0.044 Uiso 1 1 calc R . . H24B H -0.1670 0.6996 0.1255 0.044 Uiso 1 1 calc R . . H24C H -0.2064 0.5780 0.1466 0.044 Uiso 1 1 calc R . . C25 C 0.31088(11) 0.53525(12) -0.00943(10) 0.0283(3) Uani 1 1 d . . . H25A H 0.3401 0.5796 -0.0818 0.042 Uiso 1 1 calc R . . H25B H 0.3178 0.4589 -0.0025 0.042 Uiso 1 1 calc R . . H25C H 0.3542 0.5527 0.0341 0.042 Uiso 1 1 calc R . . C26 C -0.25957(11) 0.64028(11) 0.32779(11) 0.0307(3) Uani 1 1 d . . . H26A H -0.2579 0.5700 0.3179 0.046 Uiso 1 1 calc R . . H26B H -0.2936 0.6920 0.2758 0.046 Uiso 1 1 calc R . . H26C H -0.3042 0.6335 0.3971 0.046 Uiso 1 1 calc R . . C27 C 0.18582(11) 0.79762(10) 0.32155(10) 0.0260(3) Uani 1 1 d . . . H27A H 0.2472 0.7564 0.2963 0.039 Uiso 1 1 calc R . . H27B H 0.1867 0.7933 0.3922 0.039 Uiso 1 1 calc R . . H27C H 0.1957 0.8731 0.2765 0.039 Uiso 1 1 calc R . . C28 C 0.31183(11) 0.60094(10) 0.45077(9) 0.0250(3) Uani 1 1 d . . . H28A H 0.2308 0.5958 0.4817 0.038 Uiso 1 1 calc R . . H28B H 0.3386 0.6765 0.4245 0.038 Uiso 1 1 calc R . . H28C H 0.3519 0.5595 0.5032 0.038 Uiso 1 1 calc R . . C29 C 0.40382(11) 0.35510(10) 0.16868(10) 0.0255(3) Uani 1 1 d . . . H29A H 0.4456 0.2967 0.2066 0.038 Uiso 1 1 calc R . . H29B H 0.4491 0.3901 0.0986 0.038 Uiso 1 1 calc R . . H29C H 0.3330 0.3256 0.1650 0.038 Uiso 1 1 calc R . . C31 C 0.33683(10) 0.06354(9) 0.30013(9) 0.0190(2) Uani 1 1 d . . . C32 C 0.22606(10) 0.06747(10) 0.35341(10) 0.0221(3) Uani 1 1 d . . . C33 C 0.14463(10) 0.09869(10) 0.29468(10) 0.0256(3) Uani 1 1 d . . . H33A H 0.0706 0.1107 0.3274 0.031 Uiso 1 1 calc R . . C34 C 0.16936(11) 0.11240(10) 0.19047(11) 0.0264(3) Uani 1 1 d . . . H34A H 0.1121 0.1340 0.1530 0.032 Uiso 1 1 calc R . . C35 C 0.27720(11) 0.09514(9) 0.13880(10) 0.0226(3) Uani 1 1 d . . . C36 C 0.36186(10) 0.07707(9) 0.19390(9) 0.0196(2) Uani 1 1 d . . . C37 C 0.51677(10) 0.11231(9) 0.35333(8) 0.0183(2) Uani 1 1 d . . . C38 C 0.48734(10) 0.18770(10) 0.40488(9) 0.0206(2) Uani 1 1 d . . . C39 C 0.57452(11) 0.24881(10) 0.41119(9) 0.0231(3) Uani 1 1 d . . . H39A H 0.5568 0.3015 0.4442 0.028 Uiso 1 1 calc R . . C40 C 0.68619(11) 0.23482(10) 0.37070(9) 0.0230(3) Uani 1 1 d . . . H40A H 0.7433 0.2759 0.3791 0.028 Uiso 1 1 calc R . . C41 C 0.71669(10) 0.16192(10) 0.31797(9) 0.0205(2) Uani 1 1 d . . . C42 C 0.62932(10) 0.10255(9) 0.30749(8) 0.0183(2) Uani 1 1 d . . . C43 C 0.67738(10) 0.08440(9) 0.13083(9) 0.0203(2) Uani 1 1 d . . . C44 C 0.78593(11) 0.10610(10) 0.06766(10) 0.0247(3) Uani 1 1 d . . . C45 C 0.79714(12) 0.18123(11) -0.03157(10) 0.0299(3) Uani 1 1 d . . . H45A H 0.8697 0.1985 -0.0768 0.036 Uiso 1 1 calc R . . C46 C 0.70487(13) 0.23058(11) -0.06486(10) 0.0301(3) Uani 1 1 d . . . H46A H 0.7164 0.2871 -0.1295 0.036 Uiso 1 1 calc R . . C47 C 0.59446(12) 0.20016(10) -0.00645(9) 0.0251(3) Uani 1 1 d . . . C48 C 0.58194(10) 0.12103(9) 0.09068(9) 0.0205(2) Uani 1 1 d . . . C49 C 0.44053(9) 0.02800(9) 0.34415(9) 0.0177(2) Uani 1 1 d . . . H49A H 0.4186 -0.0315 0.4120 0.021 Uiso 1 1 calc R . . C50 C 0.64079(9) 0.02426(9) 0.24648(9) 0.0183(2) Uani 1 1 d . . . H50A H 0.6906 -0.0362 0.2708 0.022 Uiso 1 1 calc R . . C51 C 0.48087(10) 0.04491(9) 0.15915(9) 0.0184(2) Uani 1 1 d . . . H51A H 0.4751 -0.0102 0.1258 0.022 Uiso 1 1 calc R . . C52 C 0.51754(10) -0.01537(9) 0.26253(9) 0.0181(2) Uani 1 1 d . . . C53 C 0.50422(10) -0.13694(9) 0.29055(9) 0.0214(2) Uani 1 1 d . . . H53A H 0.5225 -0.1725 0.3578 0.032 Uiso 1 1 calc R . . H53B H 0.5553 -0.1600 0.2377 0.032 Uiso 1 1 calc R . . H53C H 0.4263 -0.1565 0.2942 0.032 Uiso 1 1 calc R . . C54 C 0.18634(11) 0.02892(11) 0.46962(10) 0.0281(3) Uani 1 1 d . . . H54A H 0.1548 0.0889 0.4920 0.042 Uiso 1 1 calc R . . H54B H 0.2500 0.0016 0.5010 0.042 Uiso 1 1 calc R . . H54C H 0.1283 -0.0288 0.4913 0.042 Uiso 1 1 calc R . . C55 C 0.29223(12) 0.08253(11) 0.03409(10) 0.0299(3) Uani 1 1 d . . . H55A H 0.3705 0.0663 0.0099 0.045 Uiso 1 1 calc R . . H55B H 0.2738 0.1496 -0.0151 0.045 Uiso 1 1 calc R . . H55C H 0.2421 0.0236 0.0393 0.045 Uiso 1 1 calc R . . C56 C 0.36842(11) 0.20556(11) 0.45384(10) 0.0269(3) Uani 1 1 d . . . H56A H 0.3668 0.2715 0.4716 0.040 Uiso 1 1 calc R . . H56B H 0.3405 0.1442 0.5167 0.040 Uiso 1 1 calc R . . H56C H 0.3205 0.2126 0.4051 0.040 Uiso 1 1 calc R . . C57 C 0.83935(10) 0.14827(10) 0.27721(10) 0.0244(3) Uani 1 1 d . . . H57A H 0.8853 0.1899 0.3011 0.037 Uiso 1 1 calc R . . H57B H 0.8566 0.1740 0.2014 0.037 Uiso 1 1 calc R . . H57C H 0.8561 0.0720 0.3026 0.037 Uiso 1 1 calc R . . C58 C 0.88727(11) 0.04483(12) 0.09591(11) 0.0313(3) Uani 1 1 d . . . H58A H 0.8694 0.0030 0.1699 0.047 Uiso 1 1 calc R . . H58B H 0.9507 0.0957 0.0803 0.047 Uiso 1 1 calc R . . H58C H 0.9075 -0.0040 0.0558 0.047 Uiso 1 1 calc R . . C59 C 0.49885(13) 0.25641(11) -0.05153(10) 0.0317(3) Uani 1 1 d . . . H59A H 0.4318 0.2495 0.0043 0.048 Uiso 1 1 calc R . . H59B H 0.4825 0.2235 -0.1000 0.048 Uiso 1 1 calc R . . H59C H 0.5202 0.3328 -0.0881 0.048 Uiso 1 1 calc 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 0.0203(6) 0.0163(5) 0.0251(6) -0.0087(5) -0.0063(5) -0.0019(4) C2 0.0252(6) 0.0181(6) 0.0303(6) -0.0102(5) -0.0115(5) 0.0008(5) C3 0.0331(7) 0.0198(6) 0.0262(6) -0.0071(5) -0.0149(5) 0.0011(5) C4 0.0315(7) 0.0219(6) 0.0211(6) -0.0071(5) -0.0065(5) -0.0034(5) C5 0.0229(6) 0.0209(6) 0.0232(6) -0.0095(5) -0.0058(5) -0.0028(5) C6 0.0205(6) 0.0174(5) 0.0230(6) -0.0088(5) -0.0072(5) -0.0014(4) C7 0.0211(6) 0.0189(6) 0.0193(6) -0.0046(4) -0.0023(4) 0.0011(5) C8 0.0211(6) 0.0240(6) 0.0235(6) -0.0051(5) -0.0014(5) 0.0028(5) C9 0.0259(7) 0.0242(6) 0.0278(6) -0.0082(5) -0.0013(5) 0.0084(5) C10 0.0320(7) 0.0186(6) 0.0248(6) -0.0073(5) -0.0028(5) 0.0039(5) C11 0.0260(6) 0.0204(6) 0.0177(5) -0.0065(4) -0.0022(5) 0.0008(5) C12 0.0192(6) 0.0197(6) 0.0168(5) -0.0061(4) -0.0009(4) 0.0018(4) C13 0.0197(6) 0.0151(5) 0.0182(5) -0.0034(4) -0.0038(4) 0.0004(4) C14 0.0236(6) 0.0173(5) 0.0200(6) -0.0040(4) -0.0062(5) -0.0015(4) C15 0.0214(6) 0.0244(6) 0.0249(6) -0.0046(5) -0.0099(5) -0.0018(5) C16 0.0172(6) 0.0237(6) 0.0256(6) -0.0047(5) -0.0047(5) 0.0022(5) C17 0.0194(6) 0.0197(6) 0.0197(5) -0.0044(5) -0.0029(4) 0.0009(4) C18 0.0190(6) 0.0164(5) 0.0179(5) -0.0038(4) -0.0045(4) 0.0000(4) C19 0.0159(6) 0.0185(6) 0.0247(6) -0.0067(5) -0.0041(4) -0.0002(4) C20 0.0199(6) 0.0169(5) 0.0181(5) -0.0062(4) -0.0037(4) 0.0001(4) C21 0.0179(6) 0.0171(5) 0.0203(6) -0.0076(4) -0.0037(4) 0.0001(4) C22 0.0166(6) 0.0178(5) 0.0210(6) -0.0073(4) -0.0035(4) 0.0001(4) C23 0.0218(6) 0.0194(6) 0.0230(6) -0.0062(5) -0.0030(5) -0.0004(5) C24 0.0280(7) 0.0306(7) 0.0354(7) -0.0128(6) -0.0157(6) 0.0076(5) C25 0.0251(7) 0.0387(7) 0.0212(6) -0.0114(5) -0.0031(5) -0.0014(5) C26 0.0197(6) 0.0299(7) 0.0376(7) -0.0083(6) -0.0018(5) 0.0043(5) C27 0.0304(7) 0.0189(6) 0.0290(6) -0.0084(5) -0.0066(5) -0.0016(5) C28 0.0296(7) 0.0245(6) 0.0236(6) -0.0089(5) -0.0094(5) -0.0018(5) C29 0.0225(6) 0.0259(6) 0.0289(6) -0.0120(5) -0.0037(5) 0.0042(5) C31 0.0185(6) 0.0160(5) 0.0237(6) -0.0066(4) -0.0070(5) 0.0002(4) C32 0.0195(6) 0.0194(6) 0.0286(6) -0.0092(5) -0.0062(5) 0.0007(4) C33 0.0179(6) 0.0236(6) 0.0377(7) -0.0122(5) -0.0080(5) 0.0032(5) C34 0.0250(7) 0.0223(6) 0.0381(7) -0.0115(5) -0.0181(5) 0.0051(5) C35 0.0271(6) 0.0174(6) 0.0278(6) -0.0089(5) -0.0131(5) 0.0030(5) C36 0.0214(6) 0.0149(5) 0.0239(6) -0.0067(4) -0.0076(5) 0.0007(4) C37 0.0195(6) 0.0197(6) 0.0159(5) -0.0042(4) -0.0071(4) 0.0010(4) C38 0.0217(6) 0.0237(6) 0.0179(5) -0.0072(5) -0.0073(5) 0.0033(5) C39 0.0286(7) 0.0231(6) 0.0216(6) -0.0101(5) -0.0098(5) 0.0033(5) C40 0.0244(6) 0.0241(6) 0.0229(6) -0.0075(5) -0.0101(5) -0.0017(5) C41 0.0198(6) 0.0226(6) 0.0184(5) -0.0042(5) -0.0071(4) 0.0003(5) C42 0.0208(6) 0.0186(5) 0.0156(5) -0.0041(4) -0.0065(4) 0.0020(4) C43 0.0239(6) 0.0183(6) 0.0201(6) -0.0093(5) -0.0029(5) -0.0025(4) C44 0.0252(6) 0.0275(6) 0.0238(6) -0.0144(5) -0.0001(5) -0.0071(5) C45 0.0338(7) 0.0318(7) 0.0236(6) -0.0138(5) 0.0037(5) -0.0138(6) C46 0.0464(8) 0.0241(6) 0.0181(6) -0.0068(5) -0.0023(5) -0.0109(6) C47 0.0388(7) 0.0196(6) 0.0193(6) -0.0087(5) -0.0074(5) -0.0029(5) C48 0.0262(6) 0.0181(6) 0.0191(6) -0.0094(5) -0.0038(5) -0.0011(5) C49 0.0164(6) 0.0186(5) 0.0176(5) -0.0055(4) -0.0038(4) 0.0010(4) C50 0.0164(6) 0.0194(5) 0.0192(5) -0.0065(4) -0.0043(4) 0.0013(4) C51 0.0220(6) 0.0162(5) 0.0189(5) -0.0068(4) -0.0068(4) 0.0010(4) C52 0.0177(6) 0.0182(5) 0.0186(5) -0.0061(4) -0.0045(4) 0.0010(4) C53 0.0204(6) 0.0188(6) 0.0246(6) -0.0060(5) -0.0063(5) 0.0010(4) C54 0.0193(6) 0.0321(7) 0.0299(7) -0.0087(5) -0.0020(5) 0.0007(5) C55 0.0379(8) 0.0284(7) 0.0329(7) -0.0145(6) -0.0207(6) 0.0065(6) C56 0.0239(7) 0.0337(7) 0.0282(6) -0.0176(5) -0.0052(5) 0.0033(5) C57 0.0195(6) 0.0293(6) 0.0261(6) -0.0098(5) -0.0071(5) -0.0014(5) C58 0.0205(6) 0.0423(8) 0.0348(7) -0.0222(6) 0.0012(5) -0.0037(6) C59 0.0506(9) 0.0225(6) 0.0236(6) -0.0049(5) -0.0156(6) 0.0005(6) _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 C6 1.4020(17) . ? C1 C2 1.4022(17) . ? C1 C19 1.5338(16) . ? C2 C3 1.3894(18) . ? C2 C24 1.5052(18) . ? C3 C4 1.3826(19) . ? C3 H3A 0.9500 . ? C4 C5 1.3904(18) . ? C4 H4A 0.9500 . ? C5 C6 1.4020(17) . ? C5 C25 1.5023(17) . ? C6 C21 1.5287(16) . ? C7 C8 1.3978(17) . ? C7 C12 1.4121(17) . ? C7 C19 1.5252(16) . ? C8 C9 1.4026(18) . ? C8 C26 1.5115(18) . ? C9 C10 1.3803(19) . ? C9 H9A 0.9500 . ? C10 C11 1.4047(18) . ? C10 H10A 0.9500 . ? C11 C12 1.3946(17) . ? C11 C27 1.5059(18) . ? C12 C20 1.5385(16) . ? C13 C14 1.3994(17) . ? C13 C18 1.4092(16) . ? C13 C20 1.5169(16) . ? C14 C15 1.3992(17) . ? C14 C28 1.5098(16) . ? C15 C16 1.3792(18) . ? C15 H15A 0.9500 . ? C16 C17 1.4029(17) . ? C16 H16A 0.9500 . ? C17 C18 1.3989(16) . ? C17 C29 1.5079(16) . ? C18 C21 1.5202(16) . ? C19 C22 1.5560(16) . ? C19 H19A 1.0000 . ? C20 C22 1.5686(15) . ? C20 H20A 1.0000 . ? C21 C22 1.5564(15) . ? C21 H21A 1.0000 . ? C22 C23 1.5236(16) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 C32 1.3969(17) . ? C31 C36 1.4078(16) . ? C31 C49 1.5259(16) . ? C32 C33 1.4004(18) . ? C32 C54 1.5083(18) . ? C33 C34 1.3796(19) . ? C33 H33A 0.9500 . ? C34 C35 1.4017(18) . ? C34 H34A 0.9500 . ? C35 C36 1.3974(17) . ? C35 C55 1.5078(17) . ? C36 C51 1.5157(16) . ? C37 C42 1.3993(16) . ? C37 C38 1.4063(16) . ? C37 C49 1.5312(16) . ? C38 C39 1.3941(18) . ? C38 C56 1.5046(17) . ? C39 C40 1.3834(18) . ? C39 H39A 0.9500 . ? C40 C41 1.3910(17) . ? C40 H40A 0.9500 . ? C41 C42 1.4079(17) . ? C41 C57 1.5035(17) . ? C42 C50 1.5318(15) . ? C43 C44 1.3963(17) . ? C43 C48 1.4103(17) . ? C43 C50 1.5219(16) . ? C44 C45 1.3983(19) . ? C44 C58 1.5096(19) . ? C45 C46 1.377(2) . ? C45 H45A 0.9500 . ? C46 C47 1.403(2) . ? C46 H46A 0.9500 . ? C47 C48 1.3965(17) . ? C47 C59 1.5091(19) . ? C48 C51 1.5372(16) . ? C49 C52 1.5606(15) . ? C49 H49A 1.0000 . ? C50 C52 1.5530(16) . ? C50 H50A 1.0000 . ? C51 C52 1.5668(15) . ? C51 H51A 1.0000 . ? C52 C53 1.5228(16) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? 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 C6 C1 C2 120.95(11) . . ? C6 C1 C19 111.65(10) . . ? C2 C1 C19 127.39(11) . . ? C3 C2 C1 117.59(12) . . ? C3 C2 C24 118.74(11) . . ? C1 C2 C24 123.66(12) . . ? C4 C3 C2 121.40(11) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 121.77(12) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C4 C5 C6 117.53(11) . . ? C4 C5 C25 118.26(11) . . ? C6 C5 C25 124.20(11) . . ? C1 C6 C5 120.64(11) . . ? C1 C6 C21 110.81(10) . . ? C5 C6 C21 128.39(11) . . ? C8 C7 C12 121.02(11) . . ? C8 C7 C19 129.45(11) . . ? C12 C7 C19 109.44(10) . . ? C7 C8 C9 116.55(12) . . ? C7 C8 C26 124.41(12) . . ? C9 C8 C26 118.88(11) . . ? C10 C9 C8 121.63(11) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 121.58(12) . . ? C9 C10 H10A 119.2 . . ? C11 C10 H10A 119.2 . . ? C12 C11 C10 117.03(12) . . ? C12 C11 C27 124.97(11) . . ? C10 C11 C27 117.99(11) . . ? C11 C12 C7 120.32(11) . . ? C11 C12 C20 130.95(11) . . ? C7 C12 C20 107.78(10) . . ? C14 C13 C18 120.83(11) . . ? C14 C13 C20 127.39(10) . . ? C18 C13 C20 110.33(10) . . ? C15 C14 C13 117.25(11) . . ? C15 C14 C28 118.58(11) . . ? C13 C14 C28 123.97(11) . . ? C16 C15 C14 121.66(11) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 121.51(11) . . ? C15 C16 H16A 119.2 . . ? C17 C16 H16A 119.2 . . ? C18 C17 C16 117.11(11) . . ? C18 C17 C29 124.18(11) . . ? C16 C17 C29 118.46(11) . . ? C17 C18 C13 120.99(11) . . ? C17 C18 C21 128.00(10) . . ? C13 C18 C21 110.26(10) . . ? C7 C19 C1 109.74(9) . . ? C7 C19 C22 104.05(9) . . ? C1 C19 C22 103.59(9) . . ? C7 C19 H19A 112.9 . . ? C1 C19 H19A 112.9 . . ? C22 C19 H19A 112.9 . . ? C13 C20 C12 126.99(10) . . ? C13 C20 C22 104.04(9) . . ? C12 C20 C22 104.84(9) . . ? C13 C20 H20A 106.5 . . ? C12 C20 H20A 106.5 . . ? C22 C20 H20A 106.5 . . ? C18 C21 C6 120.18(10) . . ? C18 C21 C22 103.54(9) . . ? C6 C21 C22 103.67(9) . . ? C18 C21 H21A 109.6 . . ? C6 C21 H21A 109.6 . . ? C22 C21 H21A 109.6 . . ? C23 C22 C19 114.07(10) . . ? C23 C22 C21 112.11(9) . . ? C19 C22 C21 108.21(9) . . ? C23 C22 C20 111.43(9) . . ? C19 C22 C20 106.20(9) . . ? C21 C22 C20 104.18(9) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C2 C24 H24A 109.5 . . ? C2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C5 C25 H25A 109.5 . . ? C5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C8 C26 H26A 109.5 . . ? C8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 C27 H27A 109.5 . . ? C11 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C11 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C14 C28 H28A 109.5 . . ? C14 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C14 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C17 C29 H29A 109.5 . . ? C17 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C17 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 120.62(11) . . ? C32 C31 C49 128.47(11) . . ? C36 C31 C49 110.18(10) . . ? C31 C32 C33 117.27(11) . . ? C31 C32 C54 124.54(11) . . ? C33 C32 C54 117.83(11) . . ? C34 C33 C32 121.59(12) . . ? C34 C33 H33A 119.2 . . ? C32 C33 H33A 119.2 . . ? C33 C34 C35 121.36(11) . . ? C33 C34 H34A 119.3 . . ? C35 C34 H34A 119.3 . . ? C36 C35 C34 117.04(11) . . ? C36 C35 C55 123.57(11) . . ? C34 C35 C55 118.87(11) . . ? C35 C36 C31 121.17(11) . . ? C35 C36 C51 126.69(11) . . ? C31 C36 C51 110.76(10) . . ? C42 C37 C38 120.59(11) . . ? C42 C37 C49 110.88(10) . . ? C38 C37 C49 128.40(11) . . ? C39 C38 C37 117.45(11) . . ? C39 C38 C56 118.43(11) . . ? C37 C38 C56 124.12(11) . . ? C40 C39 C38 121.79(11) . . ? C40 C39 H39A 119.1 . . ? C38 C39 H39A 119.1 . . ? C39 C40 C41 121.49(11) . . ? C39 C40 H40A 119.3 . . ? C41 C40 H40A 119.3 . . ? C40 C41 C42 117.36(11) . . ? C40 C41 C57 119.38(11) . . ? C42 C41 C57 123.24(11) . . ? C37 C42 C41 121.15(10) . . ? C37 C42 C50 111.76(10) . . ? C41 C42 C50 127.08(10) . . ? C44 C43 C48 121.28(11) . . ? C44 C43 C50 129.03(11) . . ? C48 C43 C50 109.68(10) . . ? C43 C44 C45 116.83(12) . . ? C43 C44 C58 123.84(12) . . ? C45 C44 C58 118.95(12) . . ? C46 C45 C44 121.15(12) . . ? C46 C45 H45A 119.4 . . ? C44 C45 H45A 119.4 . . ? C45 C46 C47 122.19(12) . . ? C45 C46 H46A 118.9 . . ? C47 C46 H46A 118.9 . . ? C48 C47 C46 116.89(12) . . ? C48 C47 C59 124.98(12) . . ? C46 C47 C59 118.11(12) . . ? C47 C48 C43 120.04(11) . . ? C47 C48 C51 130.61(11) . . ? C43 C48 C51 108.15(10) . . ? C31 C49 C37 119.54(9) . . ? C31 C49 C52 103.71(9) . . ? C37 C49 C52 103.44(9) . . ? C31 C49 H49A 109.8 . . ? C37 C49 H49A 109.8 . . ? C52 C49 H49A 109.8 . . ? C43 C50 C42 110.70(9) . . ? C43 C50 C52 104.24(9) . . ? C42 C50 C52 103.69(9) . . ? C43 C50 H50A 112.5 . . ? C42 C50 H50A 112.5 . . ? C52 C50 H50A 112.5 . . ? C36 C51 C48 126.58(10) . . ? C36 C51 C52 104.20(9) . . ? C48 C51 C52 104.82(9) . . ? C36 C51 H51A 106.6 . . ? C48 C51 H51A 106.6 . . ? C52 C51 H51A 106.6 . . ? C53 C52 C50 113.15(9) . . ? C53 C52 C49 112.82(9) . . ? C50 C52 C49 108.32(9) . . ? C53 C52 C51 111.12(9) . . ? C50 C52 C51 106.33(9) . . ? C49 C52 C51 104.53(9) . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C32 C54 H54A 109.5 . . ? C32 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C32 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C35 C55 H55A 109.5 . . ? C35 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C35 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C38 C56 H56A 109.5 . . ? C38 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C38 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C41 C57 H57A 109.5 . . ? C41 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C41 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C44 C58 H58A 109.5 . . ? C44 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C44 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C47 C59 H59A 109.5 . . ? C47 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C47 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? 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 -1.96(17) . . . . ? C19 C1 C2 C3 176.88(11) . . . . ? C6 C1 C2 C24 177.19(11) . . . . ? C19 C1 C2 C24 -3.96(19) . . . . ? C1 C2 C3 C4 -0.96(18) . . . . ? C24 C2 C3 C4 179.84(11) . . . . ? C2 C3 C4 C5 2.00(19) . . . . ? C3 C4 C5 C6 -0.06(18) . . . . ? C3 C4 C5 C25 -179.27(11) . . . . ? C2 C1 C6 C5 3.93(17) . . . . ? C19 C1 C6 C5 -175.08(10) . . . . ? C2 C1 C6 C21 -171.78(10) . . . . ? C19 C1 C6 C21 9.21(13) . . . . ? C4 C5 C6 C1 -2.85(17) . . . . ? C25 C5 C6 C1 176.31(11) . . . . ? C4 C5 C6 C21 172.03(11) . . . . ? C25 C5 C6 C21 -8.82(19) . . . . ? C12 C7 C8 C9 11.10(17) . . . . ? C19 C7 C8 C9 -165.18(12) . . . . ? C12 C7 C8 C26 -164.22(12) . . . . ? C19 C7 C8 C26 19.5(2) . . . . ? C7 C8 C9 C10 0.73(18) . . . . ? C26 C8 C9 C10 176.33(12) . . . . ? C8 C9 C10 C11 -8.0(2) . . . . ? C9 C10 C11 C12 3.23(18) . . . . ? C9 C10 C11 C27 -177.26(11) . . . . ? C10 C11 C12 C7 8.51(17) . . . . ? C27 C11 C12 C7 -170.95(11) . . . . ? C10 C11 C12 C20 -158.88(12) . . . . ? C27 C11 C12 C20 21.66(19) . . . . ? C8 C7 C12 C11 -16.11(17) . . . . ? C19 C7 C12 C11 160.85(10) . . . . ? C8 C7 C12 C20 153.92(11) . . . . ? C19 C7 C12 C20 -29.12(12) . . . . ? C18 C13 C14 C15 5.80(17) . . . . ? C20 C13 C14 C15 170.67(11) . . . . ? C18 C13 C14 C28 -169.01(11) . . . . ? C20 C13 C14 C28 -4.13(19) . . . . ? C13 C14 C15 C16 -6.63(17) . . . . ? C28 C14 C15 C16 168.46(11) . . . . ? C14 C15 C16 C17 0.56(19) . . . . ? C15 C16 C17 C18 6.31(18) . . . . ? C15 C16 C17 C29 -168.17(11) . . . . ? C16 C17 C18 C13 -7.05(17) . . . . ? C29 C17 C18 C13 167.08(11) . . . . ? C16 C17 C18 C21 -176.13(11) . . . . ? C29 C17 C18 C21 -2.00(19) . . . . ? C14 C13 C18 C17 1.05(17) . . . . ? C20 C13 C18 C17 -166.18(10) . . . . ? C14 C13 C18 C21 171.89(10) . . . . ? C20 C13 C18 C21 4.67(13) . . . . ? C8 C7 C19 C1 92.13(14) . . . . ? C12 C7 C19 C1 -84.50(12) . . . . ? C8 C7 C19 C22 -157.56(12) . . . . ? C12 C7 C19 C22 25.82(12) . . . . ? C6 C1 C19 C7 110.51(11) . . . . ? C2 C1 C19 C7 -68.43(15) . . . . ? C6 C1 C19 C22 -0.11(12) . . . . ? C2 C1 C19 C22 -179.04(11) . . . . ? C14 C13 C20 C12 85.53(16) . . . . ? C18 C13 C20 C12 -108.29(13) . . . . ? C14 C13 C20 C22 -153.21(11) . . . . ? C18 C13 C20 C22 12.96(12) . . . . ? C11 C12 C20 C13 -50.49(18) . . . . ? C7 C12 C20 C13 140.93(11) . . . . ? C11 C12 C20 C22 -171.40(12) . . . . ? C7 C12 C20 C22 20.01(12) . . . . ? C17 C18 C21 C6 -95.42(14) . . . . ? C13 C18 C21 C6 94.54(12) . . . . ? C17 C18 C21 C22 149.66(11) . . . . ? C13 C18 C21 C22 -20.38(12) . . . . ? C1 C6 C21 C18 -128.99(11) . . . . ? C5 C6 C21 C18 55.73(16) . . . . ? C1 C6 C21 C22 -14.13(12) . . . . ? C5 C6 C21 C22 170.58(11) . . . . ? C7 C19 C22 C23 110.99(11) . . . . ? C1 C19 C22 C23 -134.26(10) . . . . ? C7 C19 C22 C21 -123.49(10) . . . . ? C1 C19 C22 C21 -8.74(11) . . . . ? C7 C19 C22 C20 -12.14(11) . . . . ? C1 C19 C22 C20 102.62(10) . . . . ? C18 C21 C22 C23 -93.42(11) . . . . ? C6 C21 C22 C23 140.36(10) . . . . ? C18 C21 C22 C19 139.91(9) . . . . ? C6 C21 C22 C19 13.70(11) . . . . ? C18 C21 C22 C20 27.20(11) . . . . ? C6 C21 C22 C20 -99.02(10) . . . . ? C13 C20 C22 C23 96.36(10) . . . . ? C12 C20 C22 C23 -128.58(10) . . . . ? C13 C20 C22 C19 -138.87(9) . . . . ? C12 C20 C22 C19 -3.81(11) . . . . ? C13 C20 C22 C21 -24.72(11) . . . . ? C12 C20 C22 C21 110.34(10) . . . . ? C36 C31 C32 C33 -7.90(17) . . . . ? C49 C31 C32 C33 -177.08(11) . . . . ? C36 C31 C32 C54 164.99(11) . . . . ? C49 C31 C32 C54 -4.2(2) . . . . ? C31 C32 C33 C34 7.69(18) . . . . ? C54 C32 C33 C34 -165.69(12) . . . . ? C32 C33 C34 C35 0.31(19) . . . . ? C33 C34 C35 C36 -7.98(18) . . . . ? C33 C34 C35 C55 164.10(12) . . . . ? C34 C35 C36 C31 7.67(17) . . . . ? C55 C35 C36 C31 -164.00(12) . . . . ? C34 C35 C36 C51 173.00(11) . . . . ? C55 C35 C36 C51 1.33(19) . . . . ? C32 C31 C36 C35 0.25(17) . . . . ? C49 C31 C36 C35 171.24(10) . . . . ? C32 C31 C36 C51 -167.21(10) . . . . ? C49 C31 C36 C51 3.79(13) . . . . ? C42 C37 C38 C39 -2.10(17) . . . . ? C49 C37 C38 C39 173.49(11) . . . . ? C42 C37 C38 C56 178.35(11) . . . . ? C49 C37 C38 C56 -6.06(19) . . . . ? C37 C38 C39 C40 -1.47(17) . . . . ? C56 C38 C39 C40 178.11(11) . . . . ? C38 C39 C40 C41 2.62(19) . . . . ? C39 C40 C41 C42 -0.12(17) . . . . ? C39 C40 C41 C57 -178.86(11) . . . . ? C38 C37 C42 C41 4.64(17) . . . . ? C49 C37 C42 C41 -171.66(10) . . . . ? C38 C37 C42 C50 -174.17(10) . . . . ? C49 C37 C42 C50 9.52(13) . . . . ? C40 C41 C42 C37 -3.46(16) . . . . ? C57 C41 C42 C37 175.23(11) . . . . ? C40 C41 C42 C50 175.16(11) . . . . ? C57 C41 C42 C50 -6.15(18) . . . . ? C48 C43 C44 C45 11.22(17) . . . . ? C50 C43 C44 C45 -167.47(11) . . . . ? C48 C43 C44 C58 -161.65(11) . . . . ? C50 C43 C44 C58 19.66(19) . . . . ? C43 C44 C45 C46 -0.35(18) . . . . ? C58 C44 C45 C46 172.89(12) . . . . ? C44 C45 C46 C47 -7.14(19) . . . . ? C45 C46 C47 C48 3.57(18) . . . . ? C45 C46 C47 C59 -177.75(11) . . . . ? C46 C47 C48 C43 7.21(17) . . . . ? C59 C47 C48 C43 -171.37(11) . . . . ? C46 C47 C48 C51 -158.65(12) . . . . ? C59 C47 C48 C51 22.8(2) . . . . ? C44 C43 C48 C47 -14.97(17) . . . . ? C50 C43 C48 C47 163.95(10) . . . . ? C44 C43 C48 C51 153.78(11) . . . . ? C50 C43 C48 C51 -27.30(12) . . . . ? C32 C31 C49 C37 -94.04(14) . . . . ? C36 C31 C49 C37 95.86(12) . . . . ? C32 C31 C49 C52 151.55(12) . . . . ? C36 C31 C49 C52 -18.55(12) . . . . ? C42 C37 C49 C31 -128.33(11) . . . . ? C38 C37 C49 C31 55.72(16) . . . . ? C42 C37 C49 C52 -13.78(12) . . . . ? C38 C37 C49 C52 170.28(11) . . . . ? C44 C43 C50 C42 92.39(14) . . . . ? C48 C43 C50 C42 -86.42(11) . . . . ? C44 C43 C50 C52 -156.70(12) . . . . ? C48 C43 C50 C52 24.49(12) . . . . ? C37 C42 C50 C43 110.39(11) . . . . ? C41 C42 C50 C43 -68.34(14) . . . . ? C37 C42 C50 C52 -0.87(12) . . . . ? C41 C42 C50 C52 -179.60(11) . . . . ? C35 C36 C51 C48 84.90(16) . . . . ? C31 C36 C51 C48 -108.50(12) . . . . ? C35 C36 C51 C52 -154.02(11) . . . . ? C31 C36 C51 C52 12.58(12) . . . . ? C47 C48 C51 C36 -53.58(18) . . . . ? C43 C48 C51 C36 139.27(11) . . . . ? C47 C48 C51 C52 -174.40(12) . . . . ? C43 C48 C51 C52 18.46(12) . . . . ? C43 C50 C52 C53 110.40(10) . . . . ? C42 C50 C52 C53 -133.68(10) . . . . ? C43 C50 C52 C49 -123.72(9) . . . . ? C42 C50 C52 C49 -7.80(11) . . . . ? C43 C50 C52 C51 -11.85(11) . . . . ? C42 C50 C52 C51 104.07(10) . . . . ? C31 C49 C52 C53 -95.60(11) . . . . ? C37 C49 C52 C53 138.94(10) . . . . ? C31 C49 C52 C50 138.33(9) . . . . ? C37 C49 C52 C50 12.87(11) . . . . ? C31 C49 C52 C51 25.26(11) . . . . ? C37 C49 C52 C51 -100.20(10) . . . . ? C36 C51 C52 C53 98.72(10) . . . . ? C48 C51 C52 C53 -126.63(10) . . . . ? C36 C51 C52 C50 -137.75(9) . . . . ? C48 C51 C52 C50 -3.09(11) . . . . ? C36 C51 C52 C49 -23.27(11) . . . . ? C48 C51 C52 C49 111.39(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.340 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.086 data_3 _database_code_depnum_ccdc_archive 'CCDC 837043' _publ_section_abstract ;The synthesis of sterically crowded tribenzotriquinacenes with complete and partial substitution of the ortho-positions has been achieved using a double dehydration as the cyclization step. Ortho-methylation leads to a twisting of the tribenzotriquinacene structure and opens the way for further functionalization, eventually leading to curved model compounds for defective carbon networks. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C29 H30' _chemical_formula_sum 'C29 H30' _chemical_formula_weight 378.53 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7227(9) _cell_length_b 9.7586(9) _cell_length_c 23.813(2) _cell_angle_alpha 98.641(4) _cell_angle_beta 95.323(4) _cell_angle_gamma 106.968(4) _cell_volume 2114.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9495 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details 'Sadabs 2008/1 (Brucker 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60649 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.56 _reflns_number_total 8664 _reflns_number_gt 8164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 ver. 2008.3 (Bruker AXS)' _computing_cell_refinement 'Saint+ ver. 7.53A (Bruker AXS)' _computing_data_reduction 'Saint+ ver. 7.53A (Bruker AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0357P)^2^+2.7592P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8664 _refine_ls_number_parameters 537 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1565 _refine_ls_goodness_of_fit_ref 1.175 _refine_ls_restrained_S_all 1.175 _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 0.2347(2) 0.3158(2) 0.41320(10) 0.0213(4) Uani 1 1 d . . . C2 C 0.3159(2) 0.2563(2) 0.44950(9) 0.0208(4) Uani 1 1 d . . . C3 C 0.3667(2) 0.3223(2) 0.50699(10) 0.0281(5) Uani 1 1 d . . . C4 C 0.3255(3) 0.4429(3) 0.52855(11) 0.0357(6) Uani 1 1 d . . . H4 H 0.3603 0.4914 0.5672 0.043 Uiso 1 1 calc R . . C5 C 0.2353(3) 0.4928(2) 0.49487(12) 0.0391(7) Uani 1 1 d . . . H5 H 0.2037 0.5709 0.5117 0.047 Uiso 1 1 calc R . . C6 C 0.1883(3) 0.4325(2) 0.43643(11) 0.0301(5) Uani 1 1 d . . . C7 C 0.4632(3) 0.2707(3) 0.54598(10) 0.0364(6) Uani 1 1 d . . . H7A H 0.4074 0.1777 0.5551 0.055 Uiso 1 1 calc R . . H7B H 0.5007 0.3432 0.5815 0.055 Uiso 1 1 calc R . . H7C H 0.5446 0.2576 0.5268 0.055 Uiso 1 1 calc R . . C8 C 0.0940(3) 0.4983(3) 0.40227(14) 0.0434(7) Uani 1 1 d . . . H8A H 0.0166 0.5124 0.4238 0.065 Uiso 1 1 calc R . . H8B H 0.0509 0.4327 0.3655 0.065 Uiso 1 1 calc R . . H8C H 0.1533 0.5926 0.3953 0.065 Uiso 1 1 calc R . . C9 C 0.3646(2) 0.3226(2) 0.33052(9) 0.0194(4) Uani 1 1 d . . . C10 C 0.4503(2) 0.2345(2) 0.34298(8) 0.0188(4) Uani 1 1 d . . . C11 C 0.5963(2) 0.2740(3) 0.33585(9) 0.0233(4) Uani 1 1 d . . . C12 C 0.6507(2) 0.4005(3) 0.31382(9) 0.0268(5) Uani 1 1 d . . . H12 H 0.7502 0.4309 0.3089 0.032 Uiso 1 1 calc R . . C13 C 0.5639(3) 0.4829(2) 0.29894(9) 0.0268(5) Uani 1 1 d . . . H13 H 0.6042 0.5663 0.2826 0.032 Uiso 1 1 calc R . . C14 C 0.4180(2) 0.4465(2) 0.30733(9) 0.0239(5) Uani 1 1 d . . . C15 C 0.3253(3) 0.5370(3) 0.29017(12) 0.0346(6) Uani 1 1 d . . . H15A H 0.2322 0.4728 0.2687 0.052 Uiso 1 1 calc R . . H15B H 0.3754 0.6028 0.2660 0.052 Uiso 1 1 calc R . . H15C H 0.3078 0.5945 0.3247 0.052 Uiso 1 1 calc R . . C16 C 0.6947(3) 0.1845(3) 0.34883(12) 0.0372(6) Uani 1 1 d . . . H16A H 0.6764 0.1501 0.3849 0.056 Uiso 1 1 calc R . . H16B H 0.7963 0.2448 0.3525 0.056 Uiso 1 1 calc R . . H16C H 0.6750 0.1006 0.3176 0.056 Uiso 1 1 calc R . . C17 C 0.1834(2) -0.0021(2) 0.42045(9) 0.0191(4) Uani 1 1 d . . . C18 C 0.1025(2) -0.0022(2) 0.36881(9) 0.0187(4) Uani 1 1 d . . . C19 C -0.0419(2) -0.0868(2) 0.35352(10) 0.0228(4) Uani 1 1 d . . . C20 C -0.1021(2) -0.1760(2) 0.39152(10) 0.0263(5) Uani 1 1 d . . . H20 H -0.2002 -0.2369 0.3823 0.032 Uiso 1 1 calc R . . C21 C -0.0215(3) -0.1772(2) 0.44213(10) 0.0263(5) Uani 1 1 d . . . H21 H -0.0658 -0.2395 0.4668 0.032 Uiso 1 1 calc R . . C22 C 0.1234(2) -0.0897(2) 0.45832(9) 0.0219(4) Uani 1 1 d . . . C23 C 0.2051(3) -0.0966(3) 0.51395(10) 0.0280(5) Uani 1 1 d . . . H23A H 0.3058 -0.0890 0.5090 0.042 Uiso 1 1 calc R . . H23B H 0.1589 -0.1895 0.5256 0.042 Uiso 1 1 calc R . . H23C H 0.2038 -0.0159 0.5436 0.042 Uiso 1 1 calc R . . C24 C -0.1296(3) -0.0839(3) 0.29821(10) 0.0290(5) Uani 1 1 d . . . H24A H -0.0931 -0.1288 0.2656 0.044 Uiso 1 1 calc R . . H24B H -0.1208 0.0173 0.2953 0.044 Uiso 1 1 calc R . . H24C H -0.2319 -0.1383 0.2979 0.044 Uiso 1 1 calc R . . C25 C 0.1995(2) 0.0940(2) 0.33516(9) 0.0180(4) Uani 1 1 d . . . H25 H 0.1763 0.0539 0.2930 0.022 Uiso 1 1 calc R . . C26 C 0.2153(2) 0.2586(2) 0.34845(9) 0.0194(4) Uani 1 1 d . . . H26 H 0.1362 0.2837 0.3264 0.023 Uiso 1 1 calc R . . C27 C 0.3343(2) 0.1100(2) 0.42487(9) 0.0194(4) Uani 1 1 d . . . H27 H 0.4116 0.0863 0.4486 0.023 Uiso 1 1 calc R . . C28 C 0.3545(2) 0.0981(2) 0.35995(9) 0.0185(4) Uani 1 1 d . . . C29 C 0.3878(3) -0.0440(2) 0.33870(10) 0.0258(5) Uani 1 1 d . . . H29A H 0.4070 -0.0474 0.2989 0.039 Uiso 1 1 calc R . . H29B H 0.3042 -0.1277 0.3406 0.039 Uiso 1 1 calc R . . H29C H 0.4733 -0.0475 0.3630 0.039 Uiso 1 1 calc R . . C30 C 0.6549(2) 0.0921(2) 0.16959(8) 0.0178(4) Uani 1 1 d . . . C31 C 0.7626(2) 0.0283(2) 0.15618(8) 0.0182(4) Uani 1 1 d . . . C32 C 0.7357(2) -0.1214(2) 0.15136(9) 0.0221(4) Uani 1 1 d . . . C33 C 0.6038(3) -0.2004(2) 0.16622(9) 0.0254(5) Uani 1 1 d . . . H33 H 0.5841 -0.3020 0.1654 0.031 Uiso 1 1 calc R . . C34 C 0.5009(2) -0.1353(2) 0.18216(9) 0.0243(5) Uani 1 1 d . . . H34 H 0.4140 -0.1927 0.1931 0.029 Uiso 1 1 calc R . . C35 C 0.5218(2) 0.0120(2) 0.18257(8) 0.0202(4) Uani 1 1 d . . . C36 C 0.4044(2) 0.0805(3) 0.19491(10) 0.0260(5) Uani 1 1 d . . . H36A H 0.3620 0.1004 0.1592 0.039 Uiso 1 1 calc R . . H36B H 0.4466 0.1720 0.2226 0.039 Uiso 1 1 calc R . . H36C H 0.3286 0.0135 0.2109 0.039 Uiso 1 1 calc R . . C37 C 0.8411(3) -0.1987(3) 0.13113(11) 0.0313(5) Uani 1 1 d . . . H37A H 0.8776 -0.1634 0.0972 0.047 Uiso 1 1 calc R . . H37B H 0.7914 -0.3039 0.1212 0.047 Uiso 1 1 calc R . . H37C H 0.9227 -0.1788 0.1618 0.047 Uiso 1 1 calc R . . C38 C 0.9699(2) 0.4063(2) 0.15721(9) 0.0194(4) Uani 1 1 d . . . C39 C 0.9970(2) 0.3473(2) 0.10362(9) 0.0192(4) Uani 1 1 d . . . C40 C 1.0909(2) 0.4330(2) 0.07286(10) 0.0238(5) Uani 1 1 d . . . C41 C 1.1547(2) 0.5806(3) 0.09799(12) 0.0305(5) Uani 1 1 d . . . H41 H 1.2216 0.6422 0.0788 0.037 Uiso 1 1 calc R . . C42 C 1.1226(2) 0.6391(2) 0.15008(12) 0.0298(5) Uani 1 1 d . . . H42 H 1.1649 0.7404 0.1648 0.036 Uiso 1 1 calc R . . C43 C 1.0303(2) 0.5535(2) 0.18121(10) 0.0249(5) Uani 1 1 d . . . C44 C 0.9962(3) 0.6160(3) 0.23827(11) 0.0322(5) Uani 1 1 d . . . H44A H 1.0616 0.7158 0.2515 0.048 Uiso 1 1 calc R . . H44B H 1.0096 0.5558 0.2665 0.048 Uiso 1 1 calc R . . H44C H 0.8953 0.6170 0.2339 0.048 Uiso 1 1 calc R . . C45 C 1.1249(2) 0.3742(3) 0.01542(10) 0.0307(5) Uani 1 1 d . . . H45A H 1.1392 0.2792 0.0163 0.046 Uiso 1 1 calc R . . H45B H 1.2136 0.4421 0.0071 0.046 Uiso 1 1 calc R . . H45C H 1.0439 0.3631 -0.0144 0.046 Uiso 1 1 calc R . . C46 C 0.6706(2) 0.2490(2) 0.09935(9) 0.0170(4) Uani 1 1 d . . . C47 C 0.7540(2) 0.1905(2) 0.06206(9) 0.0170(4) Uani 1 1 d . . . C48 C 0.7056(2) 0.1493(2) 0.00334(9) 0.0209(4) Uani 1 1 d . . . C49 C 0.5805(2) 0.1776(2) -0.01836(9) 0.0241(5) Uani 1 1 d . . . H49 H 0.5441 0.1471 -0.0581 0.029 Uiso 1 1 calc R . . C50 C 0.5089(2) 0.2493(2) 0.01709(10) 0.0236(4) Uani 1 1 d . . . H50 H 0.4291 0.2750 0.0007 0.028 Uiso 1 1 calc R . . C51 C 0.5512(2) 0.2851(2) 0.07652(9) 0.0211(4) Uani 1 1 d . . . C52 C 0.4645(3) 0.3617(3) 0.11200(11) 0.0296(5) Uani 1 1 d . . . H52A H 0.3662 0.2951 0.1104 0.044 Uiso 1 1 calc R . . H52B H 0.4590 0.4480 0.0967 0.044 Uiso 1 1 calc R . . H52C H 0.5122 0.3915 0.1519 0.044 Uiso 1 1 calc R . . C53 C 0.7813(3) 0.0721(3) -0.03747(10) 0.0289(5) Uani 1 1 d . . . H53A H 0.8800 0.1359 -0.0376 0.043 Uiso 1 1 calc R . . H53B H 0.7269 0.0484 -0.0763 0.043 Uiso 1 1 calc R . . H53C H 0.7859 -0.0179 -0.0250 0.043 Uiso 1 1 calc R . . C54 C 0.9020(2) 0.1875(2) 0.08851(9) 0.0185(4) Uani 1 1 d . . . H54 H 0.9444 0.1258 0.0624 0.022 Uiso 1 1 calc R . . C55 C 0.8981(2) 0.1469(2) 0.14932(9) 0.0183(4) Uani 1 1 d . . . C56 C 0.7077(2) 0.2513(2) 0.16341(8) 0.0178(4) Uani 1 1 d . . . H56 H 0.6639 0.3144 0.1882 0.021 Uiso 1 1 calc R . . C57 C 0.8736(2) 0.2867(2) 0.18165(9) 0.0180(4) Uani 1 1 d . . . H57 H 0.8997 0.2999 0.2242 0.022 Uiso 1 1 calc R . . C58 C 1.0428(3) 0.1301(3) 0.17337(11) 0.0303(5) Uani 1 1 d . . . H58A H 1.0361 0.1041 0.2114 0.045 Uiso 1 1 calc R . . H58B H 1.1206 0.2223 0.1765 0.045 Uiso 1 1 calc R . . H58C H 1.0641 0.0531 0.1476 0.045 Uiso 1 1 calc 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 0.0189(10) 0.0134(9) 0.0291(11) 0.0000(8) 0.0112(8) 0.0008(8) C2 0.0173(10) 0.0200(10) 0.0199(10) -0.0015(8) 0.0080(8) -0.0010(8) C3 0.0243(11) 0.0255(11) 0.0235(11) -0.0022(9) 0.0118(9) -0.0080(9) C4 0.0445(15) 0.0207(11) 0.0295(13) -0.0051(10) 0.0207(11) -0.0085(10) C5 0.0530(16) 0.0139(11) 0.0468(16) -0.0037(10) 0.0354(13) 0.0009(11) C6 0.0336(13) 0.0144(10) 0.0440(14) 0.0044(9) 0.0252(11) 0.0048(9) C7 0.0311(13) 0.0464(15) 0.0169(11) 0.0001(10) 0.0021(9) -0.0069(11) C8 0.0482(16) 0.0297(13) 0.0664(19) 0.0157(13) 0.0323(15) 0.0231(12) C9 0.0201(10) 0.0182(10) 0.0176(10) -0.0007(8) 0.0034(8) 0.0043(8) C10 0.0203(10) 0.0205(10) 0.0128(9) -0.0010(8) 0.0021(7) 0.0042(8) C11 0.0201(10) 0.0321(12) 0.0149(10) -0.0006(8) 0.0012(8) 0.0066(9) C12 0.0194(10) 0.0350(13) 0.0199(10) 0.0002(9) 0.0048(8) 0.0010(9) C13 0.0304(12) 0.0223(11) 0.0214(11) 0.0018(9) 0.0071(9) -0.0011(9) C14 0.0288(11) 0.0189(10) 0.0221(11) 0.0017(8) 0.0046(9) 0.0049(9) C15 0.0399(14) 0.0268(12) 0.0438(15) 0.0170(11) 0.0136(11) 0.0130(11) C16 0.0236(12) 0.0541(17) 0.0398(14) 0.0161(12) 0.0070(10) 0.0166(12) C17 0.0223(10) 0.0151(9) 0.0212(10) 0.0003(8) 0.0060(8) 0.0085(8) C18 0.0207(10) 0.0137(9) 0.0212(10) -0.0009(8) 0.0044(8) 0.0064(8) C19 0.0229(11) 0.0170(10) 0.0268(11) -0.0035(8) 0.0048(9) 0.0072(8) C20 0.0227(11) 0.0177(10) 0.0358(13) -0.0006(9) 0.0099(9) 0.0034(9) C21 0.0333(12) 0.0162(10) 0.0329(12) 0.0053(9) 0.0168(10) 0.0088(9) C22 0.0305(11) 0.0176(10) 0.0222(10) 0.0028(8) 0.0109(9) 0.0127(9) C23 0.0400(13) 0.0278(12) 0.0234(11) 0.0100(9) 0.0130(10) 0.0164(10) C24 0.0235(11) 0.0249(11) 0.0341(13) -0.0026(9) -0.0024(9) 0.0066(9) C25 0.0201(10) 0.0158(9) 0.0167(9) 0.0004(7) 0.0018(8) 0.0051(8) C26 0.0185(10) 0.0154(10) 0.0243(11) 0.0027(8) 0.0032(8) 0.0055(8) C27 0.0200(10) 0.0235(10) 0.0161(10) 0.0035(8) 0.0038(8) 0.0087(8) C28 0.0210(10) 0.0194(10) 0.0159(9) 0.0023(8) 0.0031(8) 0.0079(8) C29 0.0317(12) 0.0267(11) 0.0245(11) 0.0053(9) 0.0085(9) 0.0156(10) C30 0.0192(10) 0.0216(10) 0.0100(9) 0.0009(7) 0.0002(7) 0.0043(8) C31 0.0191(10) 0.0200(10) 0.0145(9) 0.0040(8) 0.0004(7) 0.0047(8) C32 0.0269(11) 0.0204(10) 0.0185(10) 0.0043(8) 0.0003(8) 0.0071(9) C33 0.0312(12) 0.0184(10) 0.0216(11) 0.0059(8) -0.0027(9) 0.0007(9) C34 0.0221(11) 0.0267(11) 0.0180(10) 0.0051(8) 0.0000(8) -0.0011(9) C35 0.0191(10) 0.0260(11) 0.0112(9) 0.0011(8) -0.0002(7) 0.0024(8) C36 0.0183(10) 0.0344(12) 0.0214(11) -0.0002(9) 0.0050(8) 0.0043(9) C37 0.0388(14) 0.0223(11) 0.0367(13) 0.0057(10) 0.0063(11) 0.0152(10) C38 0.0119(9) 0.0209(10) 0.0247(11) 0.0049(8) -0.0020(8) 0.0050(8) C39 0.0125(9) 0.0214(10) 0.0246(10) 0.0075(8) 0.0004(8) 0.0059(8) C40 0.0129(9) 0.0301(12) 0.0308(12) 0.0139(9) 0.0024(8) 0.0062(8) C41 0.0139(10) 0.0295(12) 0.0485(15) 0.0202(11) 0.0013(10) 0.0021(9) C42 0.0173(10) 0.0192(11) 0.0507(15) 0.0074(10) -0.0027(10) 0.0041(9) C43 0.0159(10) 0.0195(10) 0.0374(13) 0.0028(9) -0.0046(9) 0.0063(8) C44 0.0265(12) 0.0231(11) 0.0413(14) -0.0069(10) -0.0047(10) 0.0084(9) C45 0.0204(11) 0.0439(14) 0.0312(12) 0.0193(11) 0.0084(9) 0.0077(10) C46 0.0149(9) 0.0139(9) 0.0195(10) 0.0023(7) 0.0013(7) 0.0014(7) C47 0.0173(9) 0.0134(9) 0.0192(10) 0.0054(7) 0.0029(8) 0.0021(7) C48 0.0208(10) 0.0190(10) 0.0190(10) 0.0037(8) 0.0049(8) -0.0003(8) C49 0.0230(11) 0.0266(11) 0.0173(10) 0.0072(8) -0.0005(8) -0.0011(9) C50 0.0160(10) 0.0274(11) 0.0261(11) 0.0103(9) -0.0017(8) 0.0037(8) C51 0.0181(10) 0.0177(10) 0.0260(11) 0.0046(8) 0.0022(8) 0.0034(8) C52 0.0237(11) 0.0305(12) 0.0361(13) 0.0028(10) 0.0006(10) 0.0134(10) C53 0.0315(12) 0.0308(12) 0.0204(11) -0.0007(9) 0.0067(9) 0.0054(10) C54 0.0178(10) 0.0187(10) 0.0202(10) 0.0047(8) 0.0058(8) 0.0059(8) C55 0.0183(10) 0.0172(10) 0.0204(10) 0.0047(8) 0.0031(8) 0.0064(8) C56 0.0172(10) 0.0187(10) 0.0170(10) 0.0009(8) 0.0023(7) 0.0059(8) C57 0.0171(10) 0.0190(10) 0.0169(9) 0.0017(8) 0.0004(7) 0.0055(8) C58 0.0281(12) 0.0334(13) 0.0329(13) 0.0101(10) 0.0063(10) 0.0126(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 C6 1.401(3) . ? C1 C2 1.414(3) . ? C1 C26 1.533(3) . ? C2 C3 1.399(3) . ? C2 C27 1.527(3) . ? C3 C4 1.394(3) . ? C3 C7 1.500(4) . ? C4 C5 1.373(4) . ? C4 H4 0.9500 . ? C5 C6 1.404(4) . ? C5 H5 0.9500 . ? C6 C8 1.509(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.387(3) . ? C9 C10 1.403(3) . ? C9 C26 1.532(3) . ? C10 C11 1.392(3) . ? C10 C28 1.520(3) . ? C11 C12 1.394(3) . ? C11 C16 1.512(3) . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.399(3) . ? C13 H13 0.9500 . ? C14 C15 1.505(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.387(3) . ? C17 C18 1.396(3) . ? C17 C27 1.537(3) . ? C18 C19 1.387(3) . ? C18 C25 1.504(3) . ? C19 C20 1.399(3) . ? C19 C24 1.510(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 C22 1.400(3) . ? C21 H21 0.9500 . ? C22 C23 1.501(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.548(3) . ? C25 C28 1.554(3) . ? C25 H25 1.0000 . ? C26 H26 1.0000 . ? C27 C28 1.568(3) . ? C27 H27 1.0000 . ? C28 C29 1.538(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C35 1.392(3) . ? C30 C31 1.404(3) . ? C30 C56 1.521(3) . ? C31 C32 1.392(3) . ? C31 C55 1.519(3) . ? C32 C33 1.398(3) . ? C32 C37 1.511(3) . ? C33 C34 1.385(3) . ? C33 H33 0.9500 . ? C34 C35 1.391(3) . ? C34 H34 0.9500 . ? C35 C36 1.511(3) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C43 1.391(3) . ? C38 C39 1.400(3) . ? C38 C57 1.498(3) . ? C39 C40 1.390(3) . ? C39 C54 1.530(3) . ? C40 C41 1.403(3) . ? C40 C45 1.506(3) . ? C41 C42 1.387(4) . ? C41 H41 0.9500 . ? C42 C43 1.387(3) . ? C42 H42 0.9500 . ? C43 C44 1.510(3) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C51 1.396(3) . ? C46 C47 1.422(3) . ? C46 C56 1.530(3) . ? C47 C48 1.392(3) . ? C47 C54 1.526(3) . ? C48 C49 1.395(3) . ? C48 C53 1.513(3) . ? C49 C50 1.379(3) . ? C49 H49 0.9500 . ? C50 C51 1.398(3) . ? C50 H50 0.9500 . ? C51 C52 1.514(3) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 C55 1.559(3) . ? C54 H54 1.0000 . ? C55 C58 1.532(3) . ? C55 C57 1.555(3) . ? C56 C57 1.553(3) . ? C56 H56 1.0000 . ? C57 H57 1.0000 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? 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 C6 C1 C2 119.7(2) . . ? C6 C1 C26 122.6(2) . . ? C2 C1 C26 117.33(17) . . ? C3 C2 C1 121.4(2) . . ? C3 C2 C27 121.2(2) . . ? C1 C2 C27 117.14(18) . . ? C4 C3 C2 117.6(2) . . ? C4 C3 C7 118.9(2) . . ? C2 C3 C7 123.5(2) . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 122.2(2) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C1 C6 C5 117.5(2) . . ? C1 C6 C8 124.0(2) . . ? C5 C6 C8 118.5(2) . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 122.02(19) . . ? C14 C9 C26 129.85(19) . . ? C10 C9 C26 108.11(17) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 C28 130.44(19) . . ? C9 C10 C28 108.72(17) . . ? C10 C11 C12 117.1(2) . . ? C10 C11 C16 123.3(2) . . ? C12 C11 C16 119.6(2) . . ? C13 C12 C11 121.9(2) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C9 C14 C13 116.6(2) . . ? C9 C14 C15 122.8(2) . . ? C13 C14 C15 120.5(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 121.3(2) . . ? C22 C17 C27 130.91(19) . . ? C18 C17 C27 107.80(17) . . ? C19 C18 C17 121.9(2) . . ? C19 C18 C25 129.09(19) . . ? C17 C18 C25 108.95(18) . . ? C18 C19 C20 116.8(2) . . ? C18 C19 C24 121.6(2) . . ? C20 C19 C24 121.5(2) . . ? C21 C20 C19 121.2(2) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 122.2(2) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C17 C22 C21 116.6(2) . . ? C17 C22 C23 123.9(2) . . ? C21 C22 C23 119.5(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C25 C26 116.74(16) . . ? C18 C25 C28 103.44(16) . . ? C26 C25 C28 100.10(16) . . ? C18 C25 H25 111.9 . . ? C26 C25 H25 111.9 . . ? C28 C25 H25 111.9 . . ? C9 C26 C1 105.22(16) . . ? C9 C26 C25 100.19(15) . . ? C1 C26 C25 111.60(17) . . ? C9 C26 H26 113.0 . . ? C1 C26 H26 113.0 . . ? C25 C26 H26 113.0 . . ? C2 C27 C17 105.04(16) . . ? C2 C27 C28 111.82(17) . . ? C17 C27 C28 100.76(16) . . ? C2 C27 H27 112.8 . . ? C17 C27 H27 112.8 . . ? C28 C27 H27 112.8 . . ? C10 C28 C29 115.78(17) . . ? C10 C28 C25 102.51(16) . . ? C29 C28 C25 112.60(17) . . ? C10 C28 C27 116.18(17) . . ? C29 C28 C27 109.92(17) . . ? C25 C28 C27 98.21(15) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C35 C30 C31 122.19(19) . . ? C35 C30 C56 129.30(19) . . ? C31 C30 C56 108.40(17) . . ? C32 C31 C30 120.58(19) . . ? C32 C31 C55 130.51(19) . . ? C30 C31 C55 108.91(17) . . ? C31 C32 C33 116.7(2) . . ? C31 C32 C37 123.1(2) . . ? C33 C32 C37 120.2(2) . . ? C34 C33 C32 122.1(2) . . ? C34 C33 H33 118.9 . . ? C32 C33 H33 118.9 . . ? C33 C34 C35 121.5(2) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C34 C35 C30 116.5(2) . . ? C34 C35 C36 121.64(19) . . ? C30 C35 C36 121.8(2) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C43 C38 C39 122.1(2) . . ? C43 C38 C57 128.9(2) . . ? C39 C38 C57 109.04(17) . . ? C40 C39 C38 121.1(2) . . ? C40 C39 C54 131.2(2) . . ? C38 C39 C54 107.58(17) . . ? C39 C40 C41 116.6(2) . . ? C39 C40 C45 123.1(2) . . ? C41 C40 C45 120.4(2) . . ? C42 C41 C40 121.8(2) . . ? C42 C41 H41 119.1 . . ? C40 C41 H41 119.1 . . ? C41 C42 C43 121.8(2) . . ? C41 C42 H42 119.1 . . ? C43 C42 H42 119.1 . . ? C42 C43 C38 116.6(2) . . ? C42 C43 C44 122.1(2) . . ? C38 C43 C44 121.3(2) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C40 C45 H45A 109.5 . . ? C40 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C40 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C51 C46 C47 119.96(19) . . ? C51 C46 C56 123.09(18) . . ? C47 C46 C56 116.53(17) . . ? C48 C47 C46 120.33(19) . . ? C48 C47 C54 122.29(18) . . ? C46 C47 C54 117.18(17) . . ? C47 C48 C49 118.47(19) . . ? C47 C48 C53 122.6(2) . . ? C49 C48 C53 118.9(2) . . ? C50 C49 C48 121.0(2) . . ? C50 C49 H49 119.5 . . ? C48 C49 H49 119.5 . . ? C49 C50 C51 121.5(2) . . ? C49 C50 H50 119.3 . . ? C51 C50 H50 119.3 . . ? C46 C51 C50 118.14(19) . . ? C46 C51 C52 124.2(2) . . ? C50 C51 C52 117.66(19) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C48 C53 H53A 109.5 . . ? C48 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C48 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C47 C54 C39 105.30(16) . . ? C47 C54 C55 111.90(16) . . ? C39 C54 C55 100.82(16) . . ? C47 C54 H54 112.7 . . ? C39 C54 H54 112.7 . . ? C55 C54 H54 112.7 . . ? C31 C55 C58 115.56(17) . . ? C31 C55 C57 102.18(16) . . ? C58 C55 C57 111.56(17) . . ? C31 C55 C54 115.49(17) . . ? C58 C55 C54 111.75(17) . . ? C57 C55 C54 98.42(15) . . ? C30 C56 C46 104.81(15) . . ? C30 C56 C57 100.38(15) . . ? C46 C56 C57 111.77(16) . . ? C30 C56 H56 113.0 . . ? C46 C56 H56 113.0 . . ? C57 C56 H56 113.0 . . ? C38 C57 C56 116.04(16) . . ? C38 C57 C55 103.24(16) . . ? C56 C57 C55 100.28(15) . . ? C38 C57 H57 112.1 . . ? C56 C57 H57 112.1 . . ? C55 C57 H57 112.1 . . ? C55 C58 H58A 109.5 . . ? C55 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C55 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? 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 -7.9(3) . . . . ? C26 C1 C2 C3 165.71(19) . . . . ? C6 C1 C2 C27 166.75(19) . . . . ? C26 C1 C2 C27 -19.6(3) . . . . ? C1 C2 C3 C4 4.6(3) . . . . ? C27 C2 C3 C4 -169.86(19) . . . . ? C1 C2 C3 C7 -174.9(2) . . . . ? C27 C2 C3 C7 10.6(3) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C7 C3 C4 C5 -178.9(2) . . . . ? C3 C4 C5 C6 -4.5(4) . . . . ? C2 C1 C6 C5 4.9(3) . . . . ? C26 C1 C6 C5 -168.4(2) . . . . ? C2 C1 C6 C8 -176.4(2) . . . . ? C26 C1 C6 C8 10.3(3) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C4 C5 C6 C8 -177.6(2) . . . . ? C14 C9 C10 C11 4.2(3) . . . . ? C26 C9 C10 C11 -174.26(18) . . . . ? C14 C9 C10 C28 -172.36(19) . . . . ? C26 C9 C10 C28 9.2(2) . . . . ? C9 C10 C11 C12 -2.5(3) . . . . ? C28 C10 C11 C12 173.2(2) . . . . ? C9 C10 C11 C16 179.6(2) . . . . ? C28 C10 C11 C16 -4.7(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C16 C11 C12 C13 177.2(2) . . . . ? C11 C12 C13 C14 2.5(3) . . . . ? C10 C9 C14 C13 -2.4(3) . . . . ? C26 C9 C14 C13 175.7(2) . . . . ? C10 C9 C14 C15 176.0(2) . . . . ? C26 C9 C14 C15 -5.9(4) . . . . ? C12 C13 C14 C9 -0.9(3) . . . . ? C12 C13 C14 C15 -179.3(2) . . . . ? C22 C17 C18 C19 1.6(3) . . . . ? C27 C17 C18 C19 -176.57(18) . . . . ? C22 C17 C18 C25 -175.62(17) . . . . ? C27 C17 C18 C25 6.3(2) . . . . ? C17 C18 C19 C20 -2.0(3) . . . . ? C25 C18 C19 C20 174.59(19) . . . . ? C17 C18 C19 C24 178.64(19) . . . . ? C25 C18 C19 C24 -4.8(3) . . . . ? C18 C19 C20 C21 1.1(3) . . . . ? C24 C19 C20 C21 -179.5(2) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C18 C17 C22 C21 -0.2(3) . . . . ? C27 C17 C22 C21 177.47(19) . . . . ? C18 C17 C22 C23 178.90(19) . . . . ? C27 C17 C22 C23 -3.5(3) . . . . ? C20 C21 C22 C17 -0.7(3) . . . . ? C20 C21 C22 C23 -179.8(2) . . . . ? C19 C18 C25 C26 96.9(2) . . . . ? C17 C18 C25 C26 -86.2(2) . . . . ? C19 C18 C25 C28 -154.3(2) . . . . ? C17 C18 C25 C28 22.6(2) . . . . ? C14 C9 C26 C1 -96.2(2) . . . . ? C10 C9 C26 C1 82.08(19) . . . . ? C14 C9 C26 C25 147.9(2) . . . . ? C10 C9 C26 C25 -33.8(2) . . . . ? C6 C1 C26 C9 101.5(2) . . . . ? C2 C1 C26 C9 -72.0(2) . . . . ? C6 C1 C26 C25 -150.75(19) . . . . ? C2 C1 C26 C25 35.8(2) . . . . ? C18 C25 C26 C9 154.31(17) . . . . ? C28 C25 C26 C9 43.57(18) . . . . ? C18 C25 C26 C1 43.3(2) . . . . ? C28 C25 C26 C1 -67.40(19) . . . . ? C3 C2 C27 C17 103.8(2) . . . . ? C1 C2 C27 C17 -70.9(2) . . . . ? C3 C2 C27 C28 -147.77(19) . . . . ? C1 C2 C27 C28 37.5(2) . . . . ? C22 C17 C27 C2 -93.8(2) . . . . ? C18 C17 C27 C2 84.12(19) . . . . ? C22 C17 C27 C28 150.0(2) . . . . ? C18 C17 C27 C28 -32.2(2) . . . . ? C11 C10 C28 C29 -33.9(3) . . . . ? C9 C10 C28 C29 142.23(18) . . . . ? C11 C10 C28 C25 -156.9(2) . . . . ? C9 C10 C28 C25 19.2(2) . . . . ? C11 C10 C28 C27 97.4(2) . . . . ? C9 C10 C28 C27 -86.5(2) . . . . ? C18 C25 C28 C10 -159.77(15) . . . . ? C26 C25 C28 C10 -38.94(18) . . . . ? C18 C25 C28 C29 75.1(2) . . . . ? C26 C25 C28 C29 -164.03(17) . . . . ? C18 C25 C28 C27 -40.52(18) . . . . ? C26 C25 C28 C27 80.31(17) . . . . ? C2 C27 C28 C10 40.5(2) . . . . ? C17 C27 C28 C10 151.60(17) . . . . ? C2 C27 C28 C29 174.38(17) . . . . ? C17 C27 C28 C29 -74.5(2) . . . . ? C2 C27 C28 C25 -67.89(19) . . . . ? C17 C27 C28 C25 43.25(17) . . . . ? C35 C30 C31 C32 4.6(3) . . . . ? C56 C30 C31 C32 -171.96(18) . . . . ? C35 C30 C31 C55 -175.19(18) . . . . ? C56 C30 C31 C55 8.2(2) . . . . ? C30 C31 C32 C33 -6.4(3) . . . . ? C55 C31 C32 C33 173.4(2) . . . . ? C30 C31 C32 C37 173.5(2) . . . . ? C55 C31 C32 C37 -6.7(4) . . . . ? C31 C32 C33 C34 3.3(3) . . . . ? C37 C32 C33 C34 -176.6(2) . . . . ? C32 C33 C34 C35 1.9(3) . . . . ? C33 C34 C35 C30 -3.8(3) . . . . ? C33 C34 C35 C36 174.6(2) . . . . ? C31 C30 C35 C34 0.6(3) . . . . ? C56 C30 C35 C34 176.42(19) . . . . ? C31 C30 C35 C36 -177.80(19) . . . . ? C56 C30 C35 C36 -2.0(3) . . . . ? C43 C38 C39 C40 2.6(3) . . . . ? C57 C38 C39 C40 -176.06(18) . . . . ? C43 C38 C39 C54 -174.52(18) . . . . ? C57 C38 C39 C54 6.8(2) . . . . ? C38 C39 C40 C41 -0.8(3) . . . . ? C54 C39 C40 C41 175.6(2) . . . . ? C38 C39 C40 C45 179.27(19) . . . . ? C54 C39 C40 C45 -4.4(3) . . . . ? C39 C40 C41 C42 -1.8(3) . . . . ? C45 C40 C41 C42 178.2(2) . . . . ? C40 C41 C42 C43 2.7(3) . . . . ? C41 C42 C43 C38 -0.8(3) . . . . ? C41 C42 C43 C44 179.3(2) . . . . ? C39 C38 C43 C42 -1.8(3) . . . . ? C57 C38 C43 C42 176.6(2) . . . . ? C39 C38 C43 C44 178.15(19) . . . . ? C57 C38 C43 C44 -3.5(3) . . . . ? C51 C46 C47 C48 -9.3(3) . . . . ? C56 C46 C47 C48 163.43(18) . . . . ? C51 C46 C47 C54 165.68(18) . . . . ? C56 C46 C47 C54 -21.6(3) . . . . ? C46 C47 C48 C49 5.1(3) . . . . ? C54 C47 C48 C49 -169.63(19) . . . . ? C46 C47 C48 C53 -173.41(19) . . . . ? C54 C47 C48 C53 11.8(3) . . . . ? C47 C48 C49 C50 2.2(3) . . . . ? C53 C48 C49 C50 -179.2(2) . . . . ? C48 C49 C50 C51 -5.6(3) . . . . ? C47 C46 C51 C50 6.0(3) . . . . ? C56 C46 C51 C50 -166.27(19) . . . . ? C47 C46 C51 C52 -173.6(2) . . . . ? C56 C46 C51 C52 14.1(3) . . . . ? C49 C50 C51 C46 1.3(3) . . . . ? C49 C50 C51 C52 -179.1(2) . . . . ? C48 C47 C54 C39 105.3(2) . . . . ? C46 C47 C54 C39 -69.7(2) . . . . ? C48 C47 C54 C55 -146.09(19) . . . . ? C46 C47 C54 C55 39.0(2) . . . . ? C40 C39 C54 C47 -92.9(2) . . . . ? C38 C39 C54 C47 83.85(19) . . . . ? C40 C39 C54 C55 150.6(2) . . . . ? C38 C39 C54 C55 -32.6(2) . . . . ? C32 C31 C55 C58 -38.6(3) . . . . ? C30 C31 C55 C58 141.16(19) . . . . ? C32 C31 C55 C57 -160.0(2) . . . . ? C30 C31 C55 C57 19.8(2) . . . . ? C32 C31 C55 C54 94.5(3) . . . . ? C30 C31 C55 C54 -85.8(2) . . . . ? C47 C54 C55 C31 39.9(2) . . . . ? C39 C54 C55 C31 151.37(17) . . . . ? C47 C54 C55 C58 174.68(17) . . . . ? C39 C54 C55 C58 -73.8(2) . . . . ? C47 C54 C55 C57 -68.00(19) . . . . ? C39 C54 C55 C57 43.50(17) . . . . ? C35 C30 C56 C46 -93.0(2) . . . . ? C31 C30 C56 C46 83.23(19) . . . . ? C35 C30 C56 C57 151.0(2) . . . . ? C31 C30 C56 C57 -32.8(2) . . . . ? C51 C46 C56 C30 101.9(2) . . . . ? C47 C46 C56 C30 -70.6(2) . . . . ? C51 C46 C56 C57 -150.29(19) . . . . ? C47 C46 C56 C57 37.2(2) . . . . ? C43 C38 C57 C56 94.9(2) . . . . ? C39 C38 C57 C56 -86.6(2) . . . . ? C43 C38 C57 C55 -156.5(2) . . . . ? C39 C38 C57 C55 22.0(2) . . . . ? C30 C56 C57 C38 153.39(17) . . . . ? C46 C56 C57 C38 42.7(2) . . . . ? C30 C56 C57 C55 43.04(18) . . . . ? C46 C56 C57 C55 -67.62(19) . . . . ? C31 C55 C57 C38 -158.82(16) . . . . ? C58 C55 C57 C38 77.1(2) . . . . ? C54 C55 C57 C38 -40.33(18) . . . . ? C31 C55 C57 C56 -38.75(18) . . . . ? C58 C55 C57 C56 -162.80(17) . . . . ? C54 C55 C57 C56 79.74(17) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.882 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.057 data_4 _database_code_depnum_ccdc_archive 'CCDC 837044' _publ_section_abstract ;The synthesis of sterically crowded tribenzotriquinacenes with complete and partial substitution of the ortho-positions has been achieved using a double dehydration as the cyclization step. Ortho-methylation leads to a twisting of the tribenzotriquinacene structure and opens the way for further functionalization, eventually leading to curved model compounds for defective carbon networks. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H28' _chemical_formula_sum 'C28 H28' _chemical_formula_weight 364.50 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5014(4) _cell_length_b 13.1875(5) _cell_length_c 13.0975(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.852(2) _cell_angle_gamma 90.00 _cell_volume 1936.79(13) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6743 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.67 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6390 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details 'Sadabs 2008/1 (Brucker 2008)' _exptl_special_details ; The crystal was immersed in a film of perfluoropolyether oil, mounted on a polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold nitrogen (Oxford Cryostream 700). ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4131 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.76 _reflns_number_total 4131 _reflns_number_gt 3842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 ver. 2010.3 (Bruker AXS)' _computing_cell_refinement 'Saint+ ver. 7.68A (Bruker AXS)' _computing_data_reduction 'Saint+ ver. 7.68A (Bruker AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0597P)^2^+0.9518P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4131 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 C11 C 0.21863(10) 0.29550(9) 0.26326(9) 0.0152(2) Uani 1 1 d . . . H11 H 0.2667 0.2722 0.3325 0.018 Uiso 1 1 calc R . . C22 C 0.27704(10) 0.38764(9) 0.22028(9) 0.0154(2) Uani 1 1 d . . . H22 H 0.3300 0.4243 0.2797 0.018 Uiso 1 1 calc R . . C33 C 0.21018(10) 0.21258(9) 0.17739(9) 0.0149(2) Uani 1 1 d . . . H33 H 0.2321 0.1467 0.2145 0.018 Uiso 1 1 calc R . . C44 C 0.08959(10) 0.32424(9) 0.26898(9) 0.0154(2) Uani 1 1 d . . . H44 H 0.0765 0.3259 0.3419 0.018 Uiso 1 1 calc R . . C1_1 C 0.07142(10) 0.42742(9) 0.21329(9) 0.0160(2) Uani 1 1 d . . . C2_1 C -0.02954(11) 0.48973(9) 0.19817(10) 0.0197(3) Uani 1 1 d . . . C3_1 C -0.03200(11) 0.57491(10) 0.13474(11) 0.0227(3) Uani 1 1 d . . . H3_1 H -0.0990 0.6189 0.1239 0.027 Uiso 1 1 calc R . . C4_1 C 0.06090(11) 0.59663(9) 0.08744(10) 0.0215(3) Uani 1 1 d . . . H4_1 H 0.0540 0.6526 0.0408 0.026 Uiso 1 1 calc R . . C5_1 C 0.16475(11) 0.53833(9) 0.10646(9) 0.0179(3) Uani 1 1 d . . . C6_1 C 0.17000(10) 0.45447(9) 0.17281(9) 0.0154(2) Uani 1 1 d . . . C7_1 C -0.13289(12) 0.46960(11) 0.24790(12) 0.0275(3) Uani 1 1 d . . . H7A_1 H -0.1772 0.5327 0.2506 0.041 Uiso 1 1 calc R . . H7B_1 H -0.1033 0.4439 0.3191 0.041 Uiso 1 1 calc R . . H7C_1 H -0.1857 0.4191 0.2065 0.041 Uiso 1 1 calc R . . C8_1 C 0.26337(12) 0.56942(10) 0.05463(10) 0.0237(3) Uani 1 1 d . . . H8A_1 H 0.2322 0.6171 -0.0023 0.036 Uiso 1 1 calc R . . H8B_1 H 0.2950 0.5093 0.0261 0.036 Uiso 1 1 calc R . . H8C_1 H 0.3272 0.6021 0.1062 0.036 Uiso 1 1 calc R . . C1_2 C 0.35251(10) 0.33808(9) 0.15292(9) 0.0170(2) Uani 1 1 d . . . C2_2 C 0.46099(11) 0.37198(10) 0.13442(10) 0.0200(3) Uani 1 1 d . . . C3_2 C 0.52274(11) 0.30569(11) 0.08194(10) 0.0233(3) Uani 1 1 d . . . H3_2 H 0.5950 0.3276 0.0653 0.028 Uiso 1 1 calc R . . C4_2 C 0.48108(11) 0.20899(11) 0.05365(10) 0.0228(3) Uani 1 1 d . . . H4_2 H 0.5255 0.1662 0.0181 0.027 Uiso 1 1 calc R . . C5_2 C 0.37535(11) 0.17268(10) 0.07606(9) 0.0187(3) Uani 1 1 d . . . C6_2 C 0.31066(10) 0.23957(9) 0.12455(9) 0.0165(2) Uani 1 1 d . . . C7_2 C 0.51899(12) 0.47129(11) 0.17495(11) 0.0254(3) Uani 1 1 d . . . H7A_2 H 0.5993 0.4583 0.2171 0.038 Uiso 1 1 calc R . . H7B_2 H 0.4711 0.5048 0.2183 0.038 Uiso 1 1 calc R . . H7C_2 H 0.5242 0.5152 0.1157 0.038 Uiso 1 1 calc R . . C8_2 C 0.34191(12) 0.06282(10) 0.05407(10) 0.0219(3) Uani 1 1 d . . . H8A_2 H 0.2835 0.0427 0.0945 0.033 Uiso 1 1 calc R . . H8B_2 H 0.4133 0.0204 0.0742 0.033 Uiso 1 1 calc R . . H8C_2 H 0.3072 0.0541 -0.0208 0.033 Uiso 1 1 calc R . . C1_3 C 0.07660(10) 0.20723(8) 0.12669(9) 0.0154(2) Uani 1 1 d . . . C2_3 C 0.01637(11) 0.16065(9) 0.03463(9) 0.0173(3) Uani 1 1 d . . . C3_3 C -0.10511(11) 0.13969(9) 0.02600(10) 0.0200(3) Uani 1 1 d . . . H3_3 H -0.1495 0.1098 -0.0366 0.024 Uiso 1 1 calc R . . C4_3 C -0.16186(11) 0.16134(9) 0.10600(10) 0.0204(3) Uani 1 1 d . . . H4_3 H -0.2414 0.1388 0.1007 0.025 Uiso 1 1 calc R . . C5_3 C -0.10456(11) 0.21583(9) 0.19481(10) 0.0185(3) Uani 1 1 d . . . C6_3 C 0.01301(10) 0.24555(9) 0.19887(9) 0.0163(2) Uani 1 1 d . . . C7_3 C 0.07131(12) 0.13808(10) -0.05715(10) 0.0211(3) Uani 1 1 d . . . H7A_3 H 0.1488 0.1720 -0.0471 0.032 Uiso 1 1 calc R . . H7B_3 H 0.0186 0.1629 -0.1217 0.032 Uiso 1 1 calc R . . H7C_3 H 0.0822 0.0647 -0.0624 0.032 Uiso 1 1 calc R . . C8_3 C -0.16746(11) 0.22987(10) 0.28358(11) 0.0231(3) Uani 1 1 d . . . H8A_3 H -0.1755 0.1641 0.3161 0.035 Uiso 1 1 calc R . . H8B_3 H -0.2468 0.2588 0.2563 0.035 Uiso 1 1 calc R . . H8C_3 H -0.1209 0.2758 0.3359 0.035 Uiso 1 1 calc 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 C11 0.0145(5) 0.0157(6) 0.0142(5) 0.0008(4) 0.0006(4) -0.0008(4) C22 0.0138(5) 0.0161(5) 0.0148(5) 0.0002(4) 0.0002(4) -0.0019(4) C33 0.0152(5) 0.0149(5) 0.0133(5) 0.0007(4) 0.0002(4) 0.0001(4) C44 0.0147(5) 0.0168(6) 0.0143(5) 0.0000(4) 0.0025(4) -0.0012(4) C1_1 0.0170(6) 0.0154(6) 0.0142(5) -0.0027(4) 0.0007(4) -0.0011(4) C2_1 0.0175(6) 0.0182(6) 0.0223(6) -0.0037(5) 0.0025(5) -0.0001(5) C3_1 0.0192(6) 0.0178(6) 0.0290(7) -0.0015(5) 0.0007(5) 0.0036(5) C4_1 0.0235(6) 0.0148(6) 0.0233(6) 0.0016(5) -0.0008(5) -0.0004(5) C5_1 0.0186(6) 0.0162(6) 0.0173(6) -0.0011(4) 0.0007(4) -0.0023(4) C6_1 0.0157(5) 0.0147(5) 0.0141(5) -0.0027(4) -0.0001(4) -0.0012(4) C7_1 0.0220(6) 0.0246(7) 0.0382(8) 0.0004(6) 0.0113(6) 0.0049(5) C8_1 0.0252(6) 0.0221(6) 0.0241(6) 0.0057(5) 0.0060(5) -0.0013(5) C1_2 0.0151(5) 0.0192(6) 0.0151(5) 0.0025(4) 0.0000(4) 0.0010(4) C2_2 0.0156(6) 0.0234(6) 0.0197(6) 0.0037(5) 0.0012(4) -0.0011(5) C3_2 0.0158(6) 0.0316(7) 0.0227(6) 0.0038(5) 0.0052(5) -0.0010(5) C4_2 0.0202(6) 0.0292(7) 0.0193(6) 0.0005(5) 0.0054(5) 0.0048(5) C5_2 0.0187(6) 0.0213(6) 0.0145(5) 0.0014(4) 0.0005(4) 0.0026(5) C6_2 0.0144(5) 0.0196(6) 0.0140(5) 0.0026(4) -0.0006(4) 0.0009(4) C7_2 0.0186(6) 0.0262(7) 0.0307(7) 0.0008(5) 0.0039(5) -0.0060(5) C8_2 0.0245(6) 0.0207(6) 0.0200(6) -0.0013(5) 0.0036(5) 0.0036(5) C1_3 0.0153(5) 0.0124(5) 0.0172(6) 0.0031(4) 0.0007(4) -0.0012(4) C2_3 0.0208(6) 0.0118(5) 0.0169(6) 0.0025(4) -0.0008(5) 0.0005(4) C3_3 0.0217(6) 0.0146(6) 0.0192(6) 0.0014(4) -0.0053(5) -0.0027(5) C4_3 0.0154(6) 0.0171(6) 0.0259(6) 0.0041(5) -0.0016(5) -0.0024(4) C5_3 0.0165(6) 0.0162(6) 0.0217(6) 0.0041(5) 0.0021(5) 0.0001(4) C6_3 0.0163(6) 0.0149(5) 0.0160(5) 0.0027(4) 0.0000(4) -0.0009(4) C7_3 0.0252(6) 0.0186(6) 0.0172(6) -0.0015(5) -0.0005(5) 0.0006(5) C8_3 0.0179(6) 0.0253(6) 0.0268(7) 0.0021(5) 0.0061(5) -0.0027(5) _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 C11 C44 1.5496(16) . ? C11 C22 1.5535(16) . ? C11 C33 1.5561(16) . ? C11 H11 1.0000 . ? C22 C1_2 1.5165(16) . ? C22 C6_1 1.5291(16) . ? C22 H22 1.0000 . ? C33 C6_2 1.5157(16) . ? C33 C1_3 1.5337(16) . ? C33 H33 1.0000 . ? C44 C6_3 1.5284(16) . ? C44 C1_1 1.5360(16) . ? C44 H44 1.0000 . ? C1_1 C2_1 1.4001(17) . ? C1_1 C6_1 1.4005(16) . ? C2_1 C3_1 1.3937(18) . ? C2_1 C7_1 1.5007(18) . ? C3_1 C4_1 1.3790(19) . ? C3_1 H3_1 0.9500 . ? C4_1 C5_1 1.3955(18) . ? C4_1 H4_1 0.9500 . ? C5_1 C6_1 1.3995(17) . ? C5_1 C8_1 1.5027(17) . ? C7_1 H7A_1 0.9800 . ? C7_1 H7B_1 0.9800 . ? C7_1 H7C_1 0.9800 . ? C8_1 H8A_1 0.9800 . ? C8_1 H8B_1 0.9800 . ? C8_1 H8C_1 0.9800 . ? C1_2 C2_2 1.3964(17) . ? C1_2 C6_2 1.4063(17) . ? C2_2 C3_2 1.3993(19) . ? C2_2 C7_2 1.5114(18) . ? C3_2 C4_2 1.384(2) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.3974(18) . ? C4_2 H4_2 0.9500 . ? C5_2 C6_2 1.3947(17) . ? C5_2 C8_2 1.5102(18) . ? C7_2 H7A_2 0.9800 . ? C7_2 H7B_2 0.9800 . ? C7_2 H7C_2 0.9800 . ? C8_2 H8A_2 0.9800 . ? C8_2 H8B_2 0.9800 . ? C8_2 H8C_2 0.9800 . ? C1_3 C2_3 1.3926(16) . ? C1_3 C6_3 1.4112(17) . ? C2_3 C3_3 1.4039(17) . ? C2_3 C7_3 1.5070(17) . ? C3_3 C4_3 1.3819(19) . ? C3_3 H3_3 0.9500 . ? C4_3 C5_3 1.4009(18) . ? C4_3 H4_3 0.9500 . ? C5_3 C6_3 1.3975(17) . ? C5_3 C8_3 1.5112(18) . ? C7_3 H7A_3 0.9800 . ? C7_3 H7B_3 0.9800 . ? C7_3 H7C_3 0.9800 . ? C8_3 H8A_3 0.9800 . ? C8_3 H8B_3 0.9800 . ? C8_3 H8C_3 0.9800 . ? 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 C44 C11 C22 108.80(9) . . ? C44 C11 C33 107.47(9) . . ? C22 C11 C33 104.49(9) . . ? C44 C11 H11 111.9 . . ? C22 C11 H11 111.9 . . ? C33 C11 H11 111.9 . . ? C1_2 C22 C6_1 121.67(10) . . ? C1_2 C22 C11 102.91(9) . . ? C6_1 C22 C11 102.95(9) . . ? C1_2 C22 H22 109.5 . . ? C6_1 C22 H22 109.5 . . ? C11 C22 H22 109.5 . . ? C6_2 C33 C1_3 127.25(10) . . ? C6_2 C33 C11 103.51(9) . . ? C1_3 C33 C11 103.93(9) . . ? C6_2 C33 H33 106.9 . . ? C1_3 C33 H33 106.9 . . ? C11 C33 H33 106.9 . . ? C6_3 C44 C1_1 108.47(9) . . ? C6_3 C44 C11 103.59(9) . . ? C1_1 C44 C11 102.96(9) . . ? C6_3 C44 H44 113.6 . . ? C1_1 C44 H44 113.6 . . ? C11 C44 H44 113.6 . . ? C2_1 C1_1 C6_1 120.85(11) . . ? C2_1 C1_1 C44 127.44(11) . . ? C6_1 C1_1 C44 111.67(10) . . ? C3_1 C2_1 C1_1 117.61(11) . . ? C3_1 C2_1 C7_1 119.23(11) . . ? C1_1 C2_1 C7_1 123.15(12) . . ? C4_1 C3_1 C2_1 121.34(12) . . ? C4_1 C3_1 H3_1 119.3 . . ? C2_1 C3_1 H3_1 119.3 . . ? C3_1 C4_1 C5_1 121.55(12) . . ? C3_1 C4_1 H4_1 119.2 . . ? C5_1 C4_1 H4_1 119.2 . . ? C4_1 C5_1 C6_1 117.59(11) . . ? C4_1 C5_1 C8_1 118.11(11) . . ? C6_1 C5_1 C8_1 124.30(11) . . ? C5_1 C6_1 C1_1 120.63(11) . . ? C5_1 C6_1 C22 128.87(11) . . ? C1_1 C6_1 C22 110.23(10) . . ? C2_1 C7_1 H7A_1 109.5 . . ? C2_1 C7_1 H7B_1 109.5 . . ? H7A_1 C7_1 H7B_1 109.5 . . ? C2_1 C7_1 H7C_1 109.5 . . ? H7A_1 C7_1 H7C_1 109.5 . . ? H7B_1 C7_1 H7C_1 109.5 . . ? C5_1 C8_1 H8A_1 109.5 . . ? C5_1 C8_1 H8B_1 109.5 . . ? H8A_1 C8_1 H8B_1 109.5 . . ? C5_1 C8_1 H8C_1 109.5 . . ? H8A_1 C8_1 H8C_1 109.5 . . ? H8B_1 C8_1 H8C_1 109.5 . . ? C2_2 C1_2 C6_2 121.09(11) . . ? C2_2 C1_2 C22 127.74(11) . . ? C6_2 C1_2 C22 110.20(10) . . ? C1_2 C2_2 C3_2 117.13(12) . . ? C1_2 C2_2 C7_2 123.92(12) . . ? C3_2 C2_2 C7_2 118.77(11) . . ? C4_2 C3_2 C2_2 121.60(12) . . ? C4_2 C3_2 H3_2 119.2 . . ? C2_2 C3_2 H3_2 119.2 . . ? C3_2 C4_2 C5_2 121.69(12) . . ? C3_2 C4_2 H4_2 119.2 . . ? C5_2 C4_2 H4_2 119.2 . . ? C6_2 C5_2 C4_2 117.14(12) . . ? C6_2 C5_2 C8_2 123.68(11) . . ? C4_2 C5_2 C8_2 119.03(11) . . ? C5_2 C6_2 C1_2 121.24(11) . . ? C5_2 C6_2 C33 126.70(11) . . ? C1_2 C6_2 C33 110.32(10) . . ? C2_2 C7_2 H7A_2 109.5 . . ? C2_2 C7_2 H7B_2 109.5 . . ? H7A_2 C7_2 H7B_2 109.5 . . ? C2_2 C7_2 H7C_2 109.5 . . ? H7A_2 C7_2 H7C_2 109.5 . . ? H7B_2 C7_2 H7C_2 109.5 . . ? C5_2 C8_2 H8A_2 109.5 . . ? C5_2 C8_2 H8B_2 109.5 . . ? H8A_2 C8_2 H8B_2 109.5 . . ? C5_2 C8_2 H8C_2 109.5 . . ? H8A_2 C8_2 H8C_2 109.5 . . ? H8B_2 C8_2 H8C_2 109.5 . . ? C2_3 C1_3 C6_3 120.39(11) . . ? C2_3 C1_3 C33 130.74(11) . . ? C6_3 C1_3 C33 108.18(10) . . ? C1_3 C2_3 C3_3 116.81(11) . . ? C1_3 C2_3 C7_3 124.18(11) . . ? C3_3 C2_3 C7_3 118.90(11) . . ? C4_3 C3_3 C2_3 121.86(11) . . ? C4_3 C3_3 H3_3 119.1 . . ? C2_3 C3_3 H3_3 119.1 . . ? C3_3 C4_3 C5_3 121.41(11) . . ? C3_3 C4_3 H4_3 119.3 . . ? C5_3 C4_3 H4_3 119.3 . . ? C6_3 C5_3 C4_3 116.61(11) . . ? C6_3 C5_3 C8_3 124.13(11) . . ? C4_3 C5_3 C8_3 118.97(11) . . ? C5_3 C6_3 C1_3 121.02(11) . . ? C5_3 C6_3 C44 129.54(11) . . ? C1_3 C6_3 C44 109.29(10) . . ? C2_3 C7_3 H7A_3 109.5 . . ? C2_3 C7_3 H7B_3 109.5 . . ? H7A_3 C7_3 H7B_3 109.5 . . ? C2_3 C7_3 H7C_3 109.5 . . ? H7A_3 C7_3 H7C_3 109.5 . . ? H7B_3 C7_3 H7C_3 109.5 . . ? C5_3 C8_3 H8A_3 109.5 . . ? C5_3 C8_3 H8B_3 109.5 . . ? H8A_3 C8_3 H8B_3 109.5 . . ? C5_3 C8_3 H8C_3 109.5 . . ? H8A_3 C8_3 H8C_3 109.5 . . ? H8B_3 C8_3 H8C_3 109.5 . . ? 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 C44 C11 C22 C1_2 -143.30(9) . . . . ? C33 C11 C22 C1_2 -28.74(11) . . . . ? C44 C11 C22 C6_1 -16.04(11) . . . . ? C33 C11 C22 C6_1 98.52(10) . . . . ? C44 C11 C33 C6_2 141.94(9) . . . . ? C22 C11 C33 C6_2 26.45(11) . . . . ? C44 C11 C33 C1_3 7.43(11) . . . . ? C22 C11 C33 C1_3 -108.05(9) . . . . ? C22 C11 C44 C6_3 121.12(10) . . . . ? C33 C11 C44 C6_3 8.52(11) . . . . ? C22 C11 C44 C1_1 8.15(11) . . . . ? C33 C11 C44 C1_1 -104.44(10) . . . . ? C6_3 C44 C1_1 C2_1 72.37(15) . . . . ? C11 C44 C1_1 C2_1 -178.29(11) . . . . ? C6_3 C44 C1_1 C6_1 -105.48(11) . . . . ? C11 C44 C1_1 C6_1 3.85(12) . . . . ? C6_1 C1_1 C2_1 C3_1 4.97(18) . . . . ? C44 C1_1 C2_1 C3_1 -172.71(11) . . . . ? C6_1 C1_1 C2_1 C7_1 -174.18(12) . . . . ? C44 C1_1 C2_1 C7_1 8.14(19) . . . . ? C1_1 C2_1 C3_1 C4_1 0.75(19) . . . . ? C7_1 C2_1 C3_1 C4_1 179.94(12) . . . . ? C2_1 C3_1 C4_1 C5_1 -4.4(2) . . . . ? C3_1 C4_1 C5_1 C6_1 2.12(18) . . . . ? C3_1 C4_1 C5_1 C8_1 -177.90(12) . . . . ? C4_1 C5_1 C6_1 C1_1 3.60(17) . . . . ? C8_1 C5_1 C6_1 C1_1 -176.39(11) . . . . ? C4_1 C5_1 C6_1 C22 -169.80(11) . . . . ? C8_1 C5_1 C6_1 C22 10.21(19) . . . . ? C2_1 C1_1 C6_1 C5_1 -7.25(17) . . . . ? C44 C1_1 C6_1 C5_1 170.77(10) . . . . ? C2_1 C1_1 C6_1 C22 167.28(10) . . . . ? C44 C1_1 C6_1 C22 -14.71(13) . . . . ? C1_2 C22 C6_1 C5_1 -52.98(17) . . . . ? C11 C22 C6_1 C5_1 -167.26(11) . . . . ? C1_2 C22 C6_1 C1_1 133.07(11) . . . . ? C11 C22 C6_1 C1_1 18.79(12) . . . . ? C6_1 C22 C1_2 C2_2 97.96(15) . . . . ? C11 C22 C1_2 C2_2 -147.74(12) . . . . ? C6_1 C22 C1_2 C6_2 -93.32(13) . . . . ? C11 C22 C1_2 C6_2 20.98(12) . . . . ? C6_2 C1_2 C2_2 C3_2 3.13(18) . . . . ? C22 C1_2 C2_2 C3_2 170.75(11) . . . . ? C6_2 C1_2 C2_2 C7_2 -171.84(11) . . . . ? C22 C1_2 C2_2 C7_2 -4.2(2) . . . . ? C1_2 C2_2 C3_2 C4_2 -2.83(19) . . . . ? C7_2 C2_2 C3_2 C4_2 172.41(12) . . . . ? C2_2 C3_2 C4_2 C5_2 0.0(2) . . . . ? C3_2 C4_2 C5_2 C6_2 2.54(18) . . . . ? C3_2 C4_2 C5_2 C8_2 -173.21(12) . . . . ? C4_2 C5_2 C6_2 C1_2 -2.20(17) . . . . ? C8_2 C5_2 C6_2 C1_2 173.32(11) . . . . ? C4_2 C5_2 C6_2 C33 -165.66(11) . . . . ? C8_2 C5_2 C6_2 C33 9.86(19) . . . . ? C2_2 C1_2 C6_2 C5_2 -0.64(18) . . . . ? C22 C1_2 C6_2 C5_2 -170.23(10) . . . . ? C2_2 C1_2 C6_2 C33 165.27(11) . . . . ? C22 C1_2 C6_2 C33 -4.32(13) . . . . ? C1_3 C33 C6_2 C5_2 -89.68(16) . . . . ? C11 C33 C6_2 C5_2 150.73(11) . . . . ? C1_3 C33 C6_2 C1_2 105.36(13) . . . . ? C11 C33 C6_2 C1_2 -14.23(12) . . . . ? C6_2 C33 C1_3 C2_3 47.97(19) . . . . ? C11 C33 C1_3 C2_3 167.38(12) . . . . ? C6_2 C33 C1_3 C6_3 -141.81(12) . . . . ? C11 C33 C1_3 C6_3 -22.39(12) . . . . ? C6_3 C1_3 C2_3 C3_3 -9.90(17) . . . . ? C33 C1_3 C2_3 C3_3 159.32(12) . . . . ? C6_3 C1_3 C2_3 C7_3 166.08(11) . . . . ? C33 C1_3 C2_3 C7_3 -24.70(19) . . . . ? C1_3 C2_3 C3_3 C4_3 -1.85(17) . . . . ? C7_3 C2_3 C3_3 C4_3 -178.04(11) . . . . ? C2_3 C3_3 C4_3 C5_3 7.43(19) . . . . ? C3_3 C4_3 C5_3 C6_3 -0.97(18) . . . . ? C3_3 C4_3 C5_3 C8_3 -175.10(11) . . . . ? C4_3 C5_3 C6_3 C1_3 -10.84(17) . . . . ? C8_3 C5_3 C6_3 C1_3 162.96(11) . . . . ? C4_3 C5_3 C6_3 C44 164.29(11) . . . . ? C8_3 C5_3 C6_3 C44 -21.9(2) . . . . ? C2_3 C1_3 C6_3 C5_3 16.70(17) . . . . ? C33 C1_3 C6_3 C5_3 -154.72(11) . . . . ? C2_3 C1_3 C6_3 C44 -159.32(10) . . . . ? C33 C1_3 C6_3 C44 29.26(12) . . . . ? C1_1 C44 C6_3 C5_3 -90.03(14) . . . . ? C11 C44 C6_3 C5_3 161.06(12) . . . . ? C1_1 C44 C6_3 C1_3 85.55(11) . . . . ? C11 C44 C6_3 C1_3 -23.36(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.367 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.100