# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_dimethylDCPA _database_code_depnum_ccdc_archive 'CCDC 891216' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-dimethylcyclopenta[hi]aceanthrylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14' _chemical_formula_weight 254.31 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 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 10.2176(15) _cell_length_b 10.4839(15) _cell_length_c 12.2150(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.507(3) _cell_angle_gamma 90.00 _cell_volume 1307.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min -15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5479 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9471 _diffrn_reflns_av_R_equivalents 0.0991 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2374 _reflns_number_gt 1355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0938P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2374 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1124 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.1764(3) 0.3144(3) 1.1238(3) 0.0614(9) Uani 1 1 d . . . H1A H 0.2054 0.3887 1.1638 0.092 Uiso 1 1 calc R . . H1B H 0.1533 0.2488 1.1743 0.092 Uiso 1 1 calc R . . H1C H 0.1013 0.3356 1.0774 0.092 Uiso 1 1 calc R . . C2 C 0.2840(3) 0.2677(3) 1.0553(2) 0.0438(7) Uani 1 1 d . . . C3 C 0.2733(3) 0.1546(3) 0.9827(2) 0.0392(7) Uani 1 1 d . . . C4 C 0.1774(3) 0.0674(3) 0.9578(2) 0.0468(8) Uani 1 1 d . . . H4A H 0.0955 0.0742 0.9878 0.056 Uiso 1 1 calc R . . C5 C 0.2051(3) -0.0344(3) 0.8849(2) 0.0484(8) Uani 1 1 d . . . H5A H 0.1399 -0.0943 0.8687 0.058 Uiso 1 1 calc R . . C6 C 0.3225(3) -0.0479(3) 0.8381(2) 0.0447(7) Uani 1 1 d . . . H6A H 0.3358 -0.1159 0.7910 0.054 Uiso 1 1 calc R . . C7 C 0.4255(3) 0.0416(2) 0.86074(19) 0.0360(7) Uani 1 1 d . . . C8 C 0.3962(3) 0.1412(2) 0.93366(19) 0.0359(7) Uani 1 1 d . . . C9 C 0.6379(3) 0.1422(2) 0.85983(19) 0.0353(7) Uani 1 1 d . . . C10 C 0.5538(3) 0.0437(2) 0.82233(19) 0.0364(7) Uani 1 1 d . . . C11 C 0.6304(3) -0.0355(3) 0.7499(2) 0.0441(7) Uani 1 1 d . . . H11A H 0.5994 -0.1080 0.7134 0.053 Uiso 1 1 calc R . . C12 C 0.7531(3) 0.0123(3) 0.7438(2) 0.0442(7) Uani 1 1 d . . . C13 C 0.8638(3) -0.0385(3) 0.6805(2) 0.0570(9) Uani 1 1 d . . . H13A H 0.8352 -0.1131 0.6405 0.086 Uiso 1 1 calc R . . H13B H 0.9357 -0.0605 0.7302 0.086 Uiso 1 1 calc R . . H13C H 0.8915 0.0253 0.6302 0.086 Uiso 1 1 calc R . . C14 C 0.7621(3) 0.1269(3) 0.81452(19) 0.0385(7) Uani 1 1 d . . . C15 C 0.8599(3) 0.2098(3) 0.8433(2) 0.0463(8) Uani 1 1 d . . . H15A H 0.9425 0.2012 0.8150 0.056 Uiso 1 1 calc R . . C16 C 0.8334(3) 0.3099(3) 0.9178(2) 0.0492(8) Uani 1 1 d . . . H16A H 0.9000 0.3671 0.9369 0.059 Uiso 1 1 calc R . . C17 C 0.7142(3) 0.3256(3) 0.9624(2) 0.0453(7) Uani 1 1 d . . . H17A H 0.7015 0.3920 1.0113 0.054 Uiso 1 1 calc R . . C18 C 0.6089(3) 0.2402(3) 0.93415(19) 0.0369(7) Uani 1 1 d . . . C19 C 0.4809(3) 0.2382(2) 0.97214(19) 0.0366(7) Uani 1 1 d . . . C20 C 0.4069(3) 0.3155(3) 1.0484(2) 0.0438(7) Uani 1 1 d . . . H20A H 0.4394 0.3865 1.0863 0.053 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 0.057(2) 0.065(2) 0.0643(19) -0.0054(17) 0.0195(16) 0.0088(18) C2 0.0436(19) 0.0437(17) 0.0445(15) 0.0057(13) 0.0082(13) 0.0053(14) C3 0.0350(16) 0.0430(17) 0.0396(14) 0.0097(12) 0.0008(12) 0.0014(13) C4 0.0351(17) 0.0534(19) 0.0518(16) 0.0125(14) 0.0021(13) -0.0022(14) C5 0.0392(19) 0.0505(19) 0.0550(17) 0.0055(15) -0.0048(14) -0.0105(15) C6 0.049(2) 0.0430(17) 0.0416(14) 0.0017(13) -0.0062(14) -0.0038(14) C7 0.0392(17) 0.0372(15) 0.0309(12) 0.0021(11) -0.0046(11) -0.0022(13) C8 0.0357(16) 0.0382(15) 0.0336(12) 0.0053(12) -0.0004(11) -0.0003(13) C9 0.0350(17) 0.0357(15) 0.0351(13) 0.0065(12) -0.0001(11) -0.0001(12) C10 0.0373(17) 0.0395(16) 0.0320(12) 0.0018(12) -0.0021(11) 0.0012(13) C11 0.051(2) 0.0428(17) 0.0389(14) -0.0051(13) 0.0001(13) 0.0022(15) C12 0.0438(19) 0.0512(18) 0.0376(14) 0.0045(13) 0.0035(13) 0.0065(14) C13 0.054(2) 0.064(2) 0.0537(17) 0.0015(15) 0.0123(15) 0.0111(17) C14 0.0384(17) 0.0400(16) 0.0371(13) 0.0088(12) 0.0015(12) 0.0014(13) C15 0.0350(17) 0.0513(19) 0.0528(16) 0.0115(15) 0.0051(13) -0.0023(14) C16 0.0408(19) 0.0489(18) 0.0577(17) 0.0040(15) -0.0022(14) -0.0137(15) C17 0.0479(19) 0.0396(16) 0.0484(15) -0.0027(13) 0.0009(14) -0.0088(14) C18 0.0374(16) 0.0351(15) 0.0379(13) 0.0052(12) -0.0016(11) -0.0018(13) C19 0.0398(17) 0.0335(15) 0.0362(13) 0.0018(12) 0.0001(12) 0.0007(13) C20 0.0468(18) 0.0401(16) 0.0443(15) -0.0042(13) 0.0017(13) 0.0012(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.494(4) . ? C2 C20 1.358(4) . ? C2 C3 1.481(4) . ? C3 C4 1.366(4) . ? C3 C8 1.422(4) . ? C4 C5 1.426(4) . ? C5 C6 1.358(4) . ? C6 C7 1.428(4) . ? C7 C10 1.412(4) . ? C7 C8 1.413(4) . ? C8 C19 1.403(4) . ? C9 C10 1.408(4) . ? C9 C18 1.411(4) . ? C9 C14 1.415(4) . ? C10 C11 1.465(4) . ? C11 C12 1.355(4) . ? C12 C14 1.480(4) . ? C12 C13 1.496(4) . ? C14 C15 1.359(4) . ? C15 C16 1.423(4) . ? C16 C17 1.365(4) . ? C17 C18 1.430(4) . ? C18 C19 1.407(4) . ? C19 C20 1.469(3) . ? 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 C20 C2 C3 107.6(2) . . ? C20 C2 C1 128.2(3) . . ? C3 C2 C1 124.1(3) . . ? C4 C3 C8 118.6(3) . . ? C4 C3 C2 134.7(3) . . ? C8 C3 C2 106.8(2) . . ? C3 C4 C5 118.7(3) . . ? C6 C5 C4 122.9(3) . . ? C5 C6 C7 120.5(3) . . ? C10 C7 C8 115.0(2) . . ? C10 C7 C6 129.3(2) . . ? C8 C7 C6 115.7(3) . . ? C19 C8 C7 127.1(2) . . ? C19 C8 C3 109.2(2) . . ? C7 C8 C3 123.7(2) . . ? C10 C9 C18 126.9(2) . . ? C10 C9 C14 109.6(2) . . ? C18 C9 C14 123.4(2) . . ? C9 C10 C7 117.8(2) . . ? C9 C10 C11 106.1(2) . . ? C7 C10 C11 136.1(3) . . ? C12 C11 C10 110.1(3) . . ? C11 C12 C14 107.6(2) . . ? C11 C12 C13 128.2(3) . . ? C14 C12 C13 124.2(3) . . ? C15 C14 C9 119.2(3) . . ? C15 C14 C12 134.1(3) . . ? C9 C14 C12 106.6(2) . . ? C14 C15 C16 118.6(3) . . ? C17 C16 C15 122.8(3) . . ? C16 C17 C18 120.2(3) . . ? C19 C18 C9 115.2(2) . . ? C19 C18 C17 129.1(2) . . ? C9 C18 C17 115.7(2) . . ? C8 C19 C18 118.0(2) . . ? C8 C19 C20 106.6(2) . . ? C18 C19 C20 135.4(3) . . ? C2 C20 C19 109.8(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.215 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.052 data_bisTMSacetyleneDCPA _database_code_depnum_ccdc_archive 'CCDC 891217' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-bis((trimethylsilyl)ethynyl)cyclopenta[hi]aceanthrylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Si2' _chemical_formula_weight 418.67 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' Si Si 0.0817 0.0704 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1885(10) _cell_length_b 6.8198(12) _cell_length_c 16.531(3) _cell_angle_alpha 82.438(3) _cell_angle_beta 87.220(3) _cell_angle_gamma 63.216(3) _cell_volume 617.37(18) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 59 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 222 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5960 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5967 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2130 _reflns_number_gt 1674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1240P)^2^+0.0470P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2130 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1875 _refine_ls_wR_factor_gt 0.1694 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 Si1 Si 0.50873(14) 0.84551(13) 0.35046(4) 0.0558(3) Uani 1 1 d . . . C1 C 0.2618(8) 0.9499(11) 0.4227(3) 0.132(2) Uani 1 1 d . . . H1A H 0.1278 1.0780 0.3965 0.198 Uiso 1 1 calc R . . H1B H 0.3161 0.9892 0.4687 0.198 Uiso 1 1 calc R . . H1C H 0.2117 0.8372 0.4410 0.198 Uiso 1 1 calc R . . C2 C 0.7683(11) 0.5949(9) 0.3990(3) 0.1355(19) Uani 1 1 d . . . H2A H 0.8958 0.5409 0.3602 0.203 Uiso 1 1 calc R . . H2B H 0.7174 0.4828 0.4171 0.203 Uiso 1 1 calc R . . H2C H 0.8262 0.6313 0.4449 0.203 Uiso 1 1 calc R . . C3 C 0.6167(9) 1.0495(8) 0.3131(3) 0.1147(17) Uani 1 1 d . . . H3A H 0.4847 1.1817 0.2881 0.172 Uiso 1 1 calc R . . H3B H 0.7410 0.9902 0.2736 0.172 Uiso 1 1 calc R . . H3C H 0.6812 1.0839 0.3579 0.172 Uiso 1 1 calc R . . C4 C 0.3970(6) 0.7724(5) 0.26486(17) 0.0628(8) Uani 1 1 d . . . C5 C 0.3127(5) 0.7187(5) 0.21253(16) 0.0545(7) Uani 1 1 d . . . C6 C 0.2151(4) 0.6542(4) 0.15074(15) 0.0473(6) Uani 1 1 d . . . C7 C 0.2321(4) 0.7083(4) 0.06275(14) 0.0432(6) Uani 1 1 d . . . C8 C 0.3317(5) 0.8226(4) 0.01449(16) 0.0509(7) Uani 1 1 d . . . H8A H 0.4123 0.8889 0.0376 0.061 Uiso 1 1 calc R . . C9 C 0.3112(5) 0.8397(4) -0.07173(16) 0.0520(7) Uani 1 1 d . . . H9A H 0.3771 0.9204 -0.1045 0.062 Uiso 1 1 calc R . . C10 C 0.1986(4) 0.7422(4) -0.10816(15) 0.0459(6) Uani 1 1 d . . . H10A H 0.1901 0.7561 -0.1648 0.055 Uiso 1 1 calc R . . C11 C 0.0942(4) 0.6193(4) -0.05992(13) 0.0383(5) Uani 1 1 d . . . C12 C 0.1137(4) 0.6066(4) 0.02517(13) 0.0382(6) Uani 1 1 d . . . C13 C -0.0256(4) 0.5039(4) -0.08525(13) 0.0395(6) Uani 1 1 d . . . C14 C -0.0906(4) 0.4708(4) -0.16316(14) 0.0462(6) Uani 1 1 d . . . H14 H -0.0541 0.5253 -0.2138 0.055 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 Si1 0.0655(6) 0.0736(6) 0.0413(5) -0.0120(3) -0.0076(3) -0.0404(5) C1 0.112(3) 0.224(6) 0.096(3) -0.082(4) 0.032(3) -0.093(4) C2 0.157(4) 0.107(4) 0.108(3) -0.006(3) -0.061(3) -0.025(3) C3 0.155(4) 0.148(4) 0.089(3) 0.014(3) -0.036(3) -0.114(4) C4 0.0732(18) 0.081(2) 0.0495(16) -0.0146(13) -0.0050(14) -0.0456(17) C5 0.0580(16) 0.0685(18) 0.0470(15) -0.0146(11) -0.0025(12) -0.0350(15) C6 0.0471(14) 0.0560(15) 0.0436(13) -0.0134(10) -0.0034(10) -0.0251(12) C7 0.0406(12) 0.0486(14) 0.0451(14) -0.0134(10) -0.0024(10) -0.0219(11) C8 0.0510(15) 0.0571(16) 0.0590(16) -0.0124(11) -0.0023(12) -0.0354(13) C9 0.0535(15) 0.0576(16) 0.0553(15) -0.0045(11) 0.0036(12) -0.0348(14) C10 0.0487(14) 0.0530(15) 0.0394(13) -0.0031(10) 0.0018(10) -0.0267(12) C11 0.0355(11) 0.0416(13) 0.0385(12) -0.0071(9) -0.0011(9) -0.0171(10) C12 0.0352(11) 0.0448(13) 0.0388(12) -0.0095(9) 0.0003(9) -0.0206(10) C13 0.0375(12) 0.0445(14) 0.0364(12) -0.0081(9) -0.0016(9) -0.0174(11) C14 0.0486(14) 0.0574(16) 0.0363(13) -0.0085(10) -0.0010(10) -0.0262(13) _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 Si1 C4 1.822(3) . ? Si1 C1 1.826(4) . ? Si1 C3 1.826(4) . ? Si1 C2 1.853(5) . ? C4 C5 1.206(4) . ? C5 C6 1.421(3) . ? C6 C14 1.375(3) 2_565 ? C6 C7 1.463(3) . ? C7 C8 1.359(3) . ? C7 C12 1.421(3) . ? C8 C9 1.422(4) . ? C9 C10 1.361(3) . ? C10 C11 1.421(3) . ? C11 C12 1.406(3) . ? C11 C13 1.410(3) . ? C12 C13 1.404(3) 2_565 ? C13 C12 1.404(3) 2_565 ? C13 C14 1.442(3) . ? C14 C6 1.375(3) 2_565 ? 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 C4 Si1 C1 107.73(18) . . ? C4 Si1 C3 109.46(17) . . ? C1 Si1 C3 112.3(3) . . ? C4 Si1 C2 108.9(2) . . ? C1 Si1 C2 110.4(3) . . ? C3 Si1 C2 108.0(3) . . ? C5 C4 Si1 174.9(3) . . ? C4 C5 C6 179.6(3) . . ? C14 C6 C5 126.0(2) 2_565 . ? C14 C6 C7 108.4(2) 2_565 . ? C5 C6 C7 125.6(2) . . ? C8 C7 C12 118.7(2) . . ? C8 C7 C6 135.4(2) . . ? C12 C7 C6 105.8(2) . . ? C7 C8 C9 119.1(2) . . ? C10 C9 C8 122.4(2) . . ? C9 C10 C11 120.2(2) . . ? C12 C11 C13 114.4(2) . . ? C12 C11 C10 116.6(2) . . ? C13 C11 C10 129.1(2) . . ? C13 C12 C11 127.3(2) 2_565 . ? C13 C12 C7 109.8(2) 2_565 . ? C11 C12 C7 122.9(2) . . ? C12 C13 C11 118.4(2) 2_565 . ? C12 C13 C14 106.80(19) 2_565 . ? C11 C13 C14 134.8(2) . . ? C6 C14 C13 109.2(2) 2_565 . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.290 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.058 data_tetrapropylDCPA _database_code_depnum_ccdc_archive 'CCDC 891218' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,6,7-tetrapropylcyclopenta[hi]aceanthrylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34' _chemical_formula_weight 394.57 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8931(7) _cell_length_b 10.3024(15) _cell_length_c 11.9639(18) _cell_angle_alpha 85.254(3) _cell_angle_beta 80.129(3) _cell_angle_gamma 86.958(3) _cell_volume 591.68(15) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 214 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6170 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8626 _diffrn_reflns_av_R_equivalents 0.0996 _diffrn_reflns_av_sigmaI/netI 0.0978 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2144 _reflns_number_gt 1144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.098(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2144 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.002 _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 0.3545(8) -0.1625(3) 0.4471(2) 0.0974(12) Uani 1 1 d . . . H1A H 0.2146 -0.1811 0.5123 0.146 Uiso 1 1 calc R . . H1B H 0.5098 -0.1255 0.4704 0.146 Uiso 1 1 calc R . . H1C H 0.4145 -0.2416 0.4115 0.146 Uiso 1 1 calc R . . C2 C 0.2355(6) -0.0664(3) 0.3632(2) 0.0697(9) Uani 1 1 d . . . H2A H 0.1727 0.0129 0.3998 0.084 Uiso 1 1 calc R . . H2B H 0.0759 -0.1032 0.3413 0.084 Uiso 1 1 calc R . . C3 C 0.4480(6) -0.0332(3) 0.2568(2) 0.0600(8) Uani 1 1 d . . . H3A H 0.5986 0.0111 0.2786 0.072 Uiso 1 1 calc R . . H3B H 0.5250 -0.1137 0.2255 0.072 Uiso 1 1 calc R . . C4 C 0.3340(5) 0.0502(2) 0.1666(2) 0.0523(7) Uani 1 1 d . . . C5 C 0.1634(5) 0.0045(2) 0.08825(19) 0.0494(7) Uani 1 1 d . . . C6 C 0.0990(5) 0.1133(2) 0.01667(19) 0.0484(6) Uani 1 1 d . . . C7 C -0.0591(5) 0.1159(2) -0.07148(19) 0.0491(7) Uani 1 1 d . . . C8 C -0.0891(6) 0.2410(2) -0.1316(2) 0.0607(8) Uani 1 1 d . . . H8A H -0.1948 0.2503 -0.1896 0.073 Uiso 1 1 calc R . . C9 C 0.0362(6) 0.3460(3) -0.1042(2) 0.0680(9) Uani 1 1 d . . . H9A H 0.0158 0.4255 -0.1454 0.082 Uiso 1 1 calc R . . C10 C 0.1962(6) 0.3399(2) -0.0157(2) 0.0649(8) Uani 1 1 d . . . H10A H 0.2801 0.4135 0.0001 0.078 Uiso 1 1 calc R . . C11 C 0.2250(5) 0.2236(2) 0.0460(2) 0.0539(7) Uani 1 1 d . . . C12 C 0.3698(5) 0.1813(3) 0.1413(2) 0.0563(7) Uani 1 1 d . . . C13 C 0.5121(6) 0.2725(3) 0.2011(2) 0.0700(8) Uani 1 1 d . . . H13A H 0.6009 0.3381 0.1458 0.084 Uiso 1 1 calc R . . H13B H 0.6556 0.2243 0.2358 0.084 Uiso 1 1 calc R . . C14 C 0.3113(7) 0.3397(3) 0.2926(2) 0.0779(9) Uani 1 1 d . . . H14A H 0.1531 0.3760 0.2600 0.094 Uiso 1 1 calc R . . H14B H 0.2436 0.2748 0.3531 0.094 Uiso 1 1 calc R . . C15 C 0.4358(9) 0.4459(3) 0.3427(3) 0.1087(13) Uani 1 1 d . . . H15A H 0.2984 0.4836 0.3994 0.163 Uiso 1 1 calc R . . H15B H 0.4991 0.5119 0.2839 0.163 Uiso 1 1 calc R . . H15C H 0.5897 0.4106 0.3771 0.163 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 0.115(3) 0.102(3) 0.069(2) 0.0159(18) -0.013(2) 0.009(2) C2 0.069(2) 0.0801(19) 0.0554(16) -0.0025(14) -0.0028(15) 0.0073(16) C3 0.0508(17) 0.0728(18) 0.0558(15) -0.0067(13) -0.0085(13) 0.0035(13) C4 0.0426(15) 0.0637(17) 0.0482(14) -0.0049(12) -0.0026(12) 0.0038(12) C5 0.0456(16) 0.0529(15) 0.0456(13) -0.0010(11) 0.0009(12) 0.0034(12) C6 0.0477(16) 0.0476(14) 0.0462(13) -0.0032(11) 0.0024(12) -0.0015(12) C7 0.0485(16) 0.0481(15) 0.0469(13) -0.0004(11) 0.0000(12) 0.0037(12) C8 0.067(2) 0.0533(16) 0.0579(15) 0.0041(12) -0.0057(14) 0.0050(14) C9 0.081(2) 0.0471(16) 0.0711(18) 0.0032(13) -0.0040(17) 0.0018(15) C10 0.072(2) 0.0509(16) 0.0690(17) -0.0038(13) -0.0027(16) -0.0067(13) C11 0.0505(17) 0.0524(15) 0.0549(15) -0.0059(12) 0.0032(13) -0.0025(12) C12 0.0485(17) 0.0641(17) 0.0547(15) -0.0098(13) -0.0001(13) -0.0064(13) C13 0.072(2) 0.0702(18) 0.0692(18) -0.0096(15) -0.0120(16) -0.0118(15) C14 0.091(2) 0.0718(19) 0.0733(18) -0.0166(15) -0.0140(17) -0.0074(17) C15 0.140(4) 0.091(2) 0.101(3) -0.031(2) -0.020(2) -0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.517(4) . ? C2 C3 1.526(3) . ? C3 C4 1.489(3) . ? C4 C12 1.373(3) . ? C4 C5 1.477(4) . ? C5 C7 1.408(3) 2 ? C5 C6 1.409(3) . ? C6 C7 1.409(3) . ? C6 C11 1.417(4) . ? C7 C5 1.408(3) 2 ? C7 C8 1.436(3) . ? C8 C9 1.361(4) . ? C9 C10 1.416(4) . ? C10 C11 1.368(3) . ? C11 C12 1.468(4) . ? C12 C13 1.493(4) . ? C13 C14 1.526(4) . ? C14 C15 1.494(4) . ? 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 C1 C2 C3 112.1(2) . . ? C4 C3 C2 114.2(2) . . ? C12 C4 C5 108.4(2) . . ? C12 C4 C3 126.4(3) . . ? C5 C4 C3 125.2(2) . . ? C7 C5 C6 117.4(2) 2 . ? C7 C5 C4 135.4(2) 2 . ? C6 C5 C4 107.2(2) . . ? C5 C6 C7 127.2(2) . . ? C5 C6 C11 108.7(2) . . ? C7 C6 C11 124.1(2) . . ? C5 C7 C6 115.4(2) 2 . ? C5 C7 C8 129.4(2) 2 . ? C6 C7 C8 115.2(2) . . ? C9 C8 C7 120.4(3) . . ? C8 C9 C10 123.0(2) . . ? C11 C10 C9 118.8(3) . . ? C10 C11 C6 118.5(3) . . ? C10 C11 C12 134.0(3) . . ? C6 C11 C12 107.5(2) . . ? C4 C12 C11 108.1(2) . . ? C4 C12 C13 128.5(2) . . ? C11 C12 C13 123.3(2) . . ? C12 C13 C14 112.3(2) . . ? C15 C14 C13 114.0(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.054