# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email takaishi@mail.tains.tohoku.ac.jp _publ_contact_author_name 'Shinya Takaishi' loop_ _publ_author_name 'Jinpeng Li' 'Shinya Takaishi' 'Naohiro Fujinuma' 'Katsutoshi Endo' 'Masahiro Yamashita' 'Hiroyuki Matsuzaki' 'Hiroshi Okamoto' 'Kosuke Sawabe' 'Taishi Takenobu' 'Y. Iwasa' data_tmpy2 _database_code_depnum_ccdc_archive 'CCDC 832128' #TrackingRef '- tmpy2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18' _chemical_formula_weight 258.34 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 P21/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 11.230(6) _cell_length_b 5.578(3) _cell_length_c 11.275(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.863(9) _cell_angle_gamma 90.00 _cell_volume 668.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 396(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7236 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.06 _reflns_number_total 1926 _reflns_number_gt 1216 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1926 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75012(14) -0.1736(3) -0.03104(13) 0.0226(3) Uani 1 1 d . . . C2 C 0.77709(14) 0.1648(3) 0.11369(13) 0.0228(3) Uani 1 1 d . . . C3 C 0.56648(12) -0.0007(2) 0.01022(12) 0.0190(3) Uani 1 1 d . . . C4 C 0.61918(13) -0.1739(2) -0.05209(12) 0.0206(3) Uani 1 1 d . . . C5 C 0.82492(14) -0.0053(3) 0.05068(13) 0.0240(3) Uani 1 1 d . . . H1 H 0.9181(18) -0.006(3) 0.0675(16) 0.028(4) Uiso 1 1 d . . . C6 C 0.53588(15) -0.3420(3) -0.13459(13) 0.0249(4) Uani 1 1 d . . . H2 H 0.5706(18) -0.460(3) -0.1760(18) 0.035(5) Uiso 1 1 d . . . C7 C 0.64640(13) 0.1694(3) 0.09349(12) 0.0209(3) Uani 1 1 d . . . C8 C 0.86579(15) 0.3386(3) 0.20303(15) 0.0278(4) Uani 1 1 d . . . H3 H 0.949(2) 0.306(3) 0.2056(19) 0.045(5) Uiso 1 1 d . . . H4 H 0.8632(18) 0.329(3) 0.286(2) 0.043(6) Uiso 1 1 d . . . H5 H 0.8453(18) 0.506(3) 0.1738(18) 0.042(5) Uiso 1 1 d . . . C9 C 0.41067(15) -0.3401(3) -0.15398(13) 0.0245(3) Uani 1 1 d . . . H6 H 0.3568(17) -0.452(3) -0.2094(17) 0.032(5) Uiso 1 1 d . . . C10 C 0.80974(17) -0.3535(3) -0.09504(16) 0.0286(4) Uani 1 1 d . . . H7 H 0.903(2) -0.335(3) -0.0638(19) 0.047(6) Uiso 1 1 d . . . H8 H 0.7812(17) -0.334(3) -0.1849(19) 0.037(5) Uiso 1 1 d . . . H9 H 0.7938(17) -0.518(3) -0.0776(19) 0.040(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0257(8) 0.0224(7) 0.0215(7) 0.0044(5) 0.0103(5) 0.0044(6) C2 0.0257(8) 0.0242(7) 0.0175(7) 0.0032(5) 0.0056(5) -0.0025(6) C3 0.0235(7) 0.0189(6) 0.0146(6) 0.0023(5) 0.0061(5) 0.0006(6) C4 0.0256(7) 0.0197(7) 0.0171(7) 0.0025(5) 0.0078(5) 0.0023(6) C5 0.0208(7) 0.0280(8) 0.0239(7) 0.0063(6) 0.0082(6) 0.0018(6) C6 0.0328(9) 0.0225(7) 0.0212(7) -0.0021(6) 0.0112(6) 0.0023(6) C7 0.0246(8) 0.0216(7) 0.0164(6) 0.0019(5) 0.0064(5) 0.0003(6) C8 0.0249(8) 0.0310(8) 0.0255(8) -0.0019(7) 0.0054(6) -0.0054(7) C9 0.0298(8) 0.0225(7) 0.0203(7) -0.0052(6) 0.0070(6) -0.0038(6) C10 0.0310(9) 0.0278(8) 0.0314(9) 0.0001(7) 0.0163(7) 0.0042(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 C5 1.391(2) . ? C1 C4 1.412(2) . ? C1 C10 1.513(2) . ? C2 C5 1.393(2) . ? C2 C7 1.411(2) . ? C2 C8 1.516(2) . ? C3 C7 1.4293(19) . ? C3 C4 1.4302(19) . ? C3 C3 1.435(3) 3_655 ? C4 C6 1.434(2) . ? C5 H1 1.001(18) . ? C6 C9 1.351(2) . ? C6 H2 0.961(19) . ? C7 C9 1.437(2) 3_655 ? C8 H3 0.95(2) . ? C8 H4 0.95(2) . ? C8 H5 0.991(19) . ? C9 C7 1.437(2) 3_655 ? C9 H6 0.951(18) . ? C10 H7 1.00(2) . ? C10 H8 0.96(2) . ? C10 H9 0.968(18) . ? 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 C5 C1 C4 119.03(14) . . ? C5 C1 C10 119.87(14) . . ? C4 C1 C10 121.10(14) . . ? C5 C2 C7 118.85(13) . . ? C5 C2 C8 119.72(14) . . ? C7 C2 C8 121.42(14) . . ? C7 C3 C4 119.96(13) . . ? C7 C3 C3 120.09(15) . 3_655 ? C4 C3 C3 119.95(15) . 3_655 ? C1 C4 C3 119.38(13) . . ? C1 C4 C6 122.37(13) . . ? C3 C4 C6 118.25(13) . . ? C1 C5 C2 123.20(14) . . ? C1 C5 H1 119.6(10) . . ? C2 C5 H1 117.1(10) . . ? C9 C6 C4 121.75(14) . . ? C9 C6 H2 119.4(11) . . ? C4 C6 H2 118.8(11) . . ? C2 C7 C3 119.57(13) . . ? C2 C7 C9 122.39(13) . 3_655 ? C3 C7 C9 118.04(14) . 3_655 ? C2 C8 H3 109.3(12) . . ? C2 C8 H4 113.3(12) . . ? H3 C8 H4 107.7(17) . . ? C2 C8 H5 110.4(11) . . ? H3 C8 H5 108.2(16) . . ? H4 C8 H5 107.9(16) . . ? C6 C9 C7 121.91(14) . 3_655 ? C6 C9 H6 120.6(11) . . ? C7 C9 H6 117.5(11) 3_655 . ? C1 C10 H7 109.7(11) . . ? C1 C10 H8 112.1(11) . . ? H7 C10 H8 108.2(16) . . ? C1 C10 H9 113.2(12) . . ? H7 C10 H9 105.7(15) . . ? H8 C10 H9 107.5(16) . . ? 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 C5 C1 C4 C3 0.4(2) . . . . ? C10 C1 C4 C3 180.00(13) . . . . ? C5 C1 C4 C6 -179.78(13) . . . . ? C10 C1 C4 C6 -0.2(2) . . . . ? C7 C3 C4 C1 -0.40(19) . . . . ? C3 C3 C4 C1 -179.92(15) 3_655 . . . ? C7 C3 C4 C6 179.80(12) . . . . ? C3 C3 C4 C6 0.3(2) 3_655 . . . ? C4 C1 C5 C2 0.0(2) . . . . ? C10 C1 C5 C2 -179.55(14) . . . . ? C7 C2 C5 C1 -0.5(2) . . . . ? C8 C2 C5 C1 178.85(13) . . . . ? C1 C4 C6 C9 -179.93(13) . . . . ? C3 C4 C6 C9 -0.1(2) . . . . ? C5 C2 C7 C3 0.5(2) . . . . ? C8 C2 C7 C3 -178.82(13) . . . . ? C5 C2 C7 C9 -179.52(13) . . . 3_655 ? C8 C2 C7 C9 1.1(2) . . . 3_655 ? C4 C3 C7 C2 -0.09(19) . . . . ? C3 C3 C7 C2 179.43(15) 3_655 . . . ? C4 C3 C7 C9 179.96(12) . . . 3_655 ? C3 C3 C7 C9 -0.5(2) 3_655 . . 3_655 ? C4 C6 C9 C7 0.2(2) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.377 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.064 # Attachment '- tmpyper.cif' data_tmpyper _database_code_depnum_ccdc_archive 'CCDC 832129' #TrackingRef '- tmpyper.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17.24' _chemical_formula_weight 257.58 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 P21/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 11.1814(16) _cell_length_b 5.6056(8) _cell_length_c 11.1539(16) _cell_angle_alpha 90.00 _cell_angle_beta 109.102(3) _cell_angle_gamma 90.00 _cell_volume 660.61(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14629 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 30.03 _reflns_number_total 1932 _reflns_number_gt 1561 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.3198P] 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 1932 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.1891 _refine_ls_wR_factor_gt 0.1806 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.56657(16) 0.0012(3) 0.01028(14) 0.0182(4) Uani 0.874(5) 1 d P . 1 C2 C 0.22216(19) 0.1632(3) -0.11397(16) 0.0223(4) Uani 0.874(5) 1 d P . 1 C3 C 0.25011(18) -0.1743(3) 0.03103(16) 0.0222(4) Uani 0.874(5) 1 d P . 1 C4 C 0.61889(19) 0.1740(3) -0.05222(15) 0.0203(4) Uani 0.874(5) 1 d P . 1 C5 C 0.1744(2) -0.0069(3) -0.05106(16) 0.0234(4) Uani 0.874(5) 1 d P . 1 H1 H 0.0859 -0.0087 -0.0648 0.028 Uiso 0.874(5) 1 calc PR . 1 C6 C 0.53529(18) 0.3415(3) -0.13516(16) 0.0235(4) Uani 0.874(5) 1 d P . 1 H2 H 0.5691 0.4572 -0.1775 0.028 Uiso 0.874(5) 1 calc PR . 1 C7 C 0.35318(18) 0.1682(3) -0.09366(15) 0.0204(4) Uani 0.874(5) 1 d P . 1 C8 C 0.13269(19) 0.3361(4) -0.20411(18) 0.0283(4) Uani 0.874(5) 1 d P . 1 H3 H 0.0457 0.3021 -0.2075 0.042 Uiso 0.874(5) 1 calc PR . 1 H4 H 0.1395 0.3184 -0.2890 0.042 Uiso 0.874(5) 1 calc PR . 1 H5 H 0.1550 0.4997 -0.1741 0.042 Uiso 0.874(5) 1 calc PR . 1 C9 C 0.40914(18) 0.3393(3) -0.15491(16) 0.0238(4) Uani 0.874(5) 1 d P . 1 H6 H 0.3566 0.4536 -0.2106 0.029 Uiso 0.874(5) 1 calc PR . 1 C10 C 0.1903(2) -0.3542(3) 0.09525(18) 0.0278(4) Uani 0.874(5) 1 d P . 1 H7 H 0.0982 -0.3340 0.0644 0.042 Uiso 0.874(5) 1 calc PR . 1 H8 H 0.2224 -0.3291 0.1872 0.042 Uiso 0.874(5) 1 calc PR . 1 H9 H 0.2117 -0.5159 0.0757 0.042 Uiso 0.874(5) 1 calc PR . 1 C13 C 0.6330(19) -0.001(3) 0.0223(15) 0.039(4) Uiso 0.126(5) 1 d P . 2 C14 C 0.158(2) 0.175(4) -0.1305(19) 0.049(5) Uiso 0.126(5) 1 d P . 2 H10 H 0.0687 0.1731 -0.1493 0.059 Uiso 0.126(5) 1 calc PR . 2 C18 C 0.417(2) 0.176(3) -0.0840(17) 0.043(4) Uiso 0.126(5) 1 d P . 2 C24 C 0.3866(18) -0.336(3) 0.1161(17) 0.045(4) Uiso 0.126(5) 1 d P . 2 H11 H 0.4369 -0.4541 0.1706 0.054 Uiso 0.126(5) 1 calc PR . 2 C19 C 0.558(2) 0.174(4) -0.0598(19) 0.049(5) Uiso 0.126(5) 1 d P . 2 C20 C 0.337(2) 0.329(4) -0.1606(19) 0.053(5) Uiso 0.126(5) 1 d P . 2 H12 H 0.3702 0.4443 -0.2037 0.063 Uiso 0.126(5) 1 calc PR . 2 C22 C 0.229(2) 0.003(4) -0.0465(18) 0.042(5) Uiso 0.126(5) 1 d P . 2 C21 C 0.204(2) 0.328(4) -0.1817(19) 0.050(5) Uiso 0.126(5) 1 d P . 2 H13 H 0.1513 0.4450 -0.2349 0.060 Uiso 0.126(5) 1 calc PR . 2 C23 C 0.183(2) -0.174(4) 0.0161(19) 0.049(5) Uiso 0.126(5) 1 d P . 2 H14 H 0.0945 -0.1795 -0.0002 0.059 Uiso 0.126(5) 1 calc PR . 2 C25 C 0.2512(18) -0.328(3) 0.0930(16) 0.040(4) Uiso 0.126(5) 1 d P . 2 H15 H 0.2132 -0.4364 0.1350 0.048 Uiso 0.126(5) 1 calc PR . 2 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 0.0214(9) 0.0175(7) 0.0158(7) -0.0016(6) 0.0065(6) 0.0004(6) C2 0.0239(9) 0.0230(8) 0.0193(8) -0.0017(6) 0.0060(6) 0.0036(7) C3 0.0254(10) 0.0218(8) 0.0215(8) -0.0038(6) 0.0107(6) -0.0042(7) C4 0.0259(10) 0.0185(8) 0.0178(7) -0.0021(6) 0.0088(6) -0.0007(7) C5 0.0215(9) 0.0263(9) 0.0233(8) -0.0057(7) 0.0085(7) -0.0015(7) C6 0.0307(10) 0.0199(8) 0.0219(8) 0.0040(6) 0.0111(7) -0.0006(7) C7 0.0247(9) 0.0194(8) 0.0170(7) -0.0002(6) 0.0070(6) 0.0024(6) C8 0.0256(9) 0.0307(10) 0.0269(9) 0.0030(7) 0.0063(7) 0.0071(7) C9 0.0298(10) 0.0211(8) 0.0204(8) 0.0053(6) 0.0082(7) 0.0036(7) C10 0.0286(9) 0.0272(9) 0.0327(10) 0.0002(7) 0.0170(7) -0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7 1.423(2) 3_655 ? C1 C4 1.426(2) . ? C1 C1 1.430(3) 3_655 ? C2 C5 1.390(3) . ? C2 C7 1.408(3) . ? C2 C8 1.514(3) . ? C3 C5 1.389(3) . ? C3 C4 1.405(3) 3_655 ? C3 C10 1.513(3) . ? C4 C3 1.405(3) 3_655 ? C4 C6 1.430(2) . ? C5 H1 0.9500 . ? C6 C9 1.355(3) . ? C6 H2 0.9500 . ? C7 C1 1.423(2) 3_655 ? C7 C9 1.435(3) . ? C8 H3 0.9800 . ? C8 H4 0.9800 . ? C8 H5 0.9800 . ? C9 H6 0.9500 . ? C10 H7 0.9800 . ? C10 H8 0.9800 . ? C10 H9 0.9800 . ? C13 C19 1.41(3) . ? C13 C18 1.41(3) 3_655 ? C13 C22 1.47(3) 3_655 ? C14 C21 1.23(3) . ? C14 C22 1.40(3) . ? C14 H10 0.9500 . ? C18 C20 1.33(3) . ? C18 C13 1.41(3) 3_655 ? C18 C19 1.51(3) . ? C24 C19 1.36(3) 3_655 ? C24 C25 1.45(3) . ? C24 H11 0.9500 . ? C19 C24 1.36(3) 3_655 ? C20 C21 1.43(3) . ? C20 H12 0.9500 . ? C22 C23 1.40(3) . ? C22 C13 1.47(3) 3_655 ? C21 H13 0.9500 . ? C23 C25 1.28(3) . ? C23 H14 0.9500 . ? C25 H15 0.9500 . ? 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 C7 C1 C4 120.07(17) 3_655 . ? C7 C1 C1 119.96(19) 3_655 3_655 ? C4 C1 C1 119.98(19) . 3_655 ? C5 C2 C7 118.95(17) . . ? C5 C2 C8 119.66(19) . . ? C7 C2 C8 121.38(17) . . ? C5 C3 C4 119.15(17) . 3_655 ? C5 C3 C10 119.60(19) . . ? C4 C3 C10 121.25(17) 3_655 . ? C3 C4 C1 119.36(16) 3_655 . ? C3 C4 C6 122.19(16) 3_655 . ? C1 C4 C6 118.45(17) . . ? C3 C5 C2 123.0(2) . . ? C3 C5 H1 118.5 . . ? C2 C5 H1 118.5 . . ? C9 C6 C4 121.65(16) . . ? C9 C6 H2 119.2 . . ? C4 C6 H2 119.2 . . ? C2 C7 C1 119.49(16) . 3_655 ? C2 C7 C9 122.00(16) . . ? C1 C7 C9 118.51(17) 3_655 . ? C6 C9 C7 121.46(16) . . ? C6 C9 H6 119.3 . . ? C7 C9 H6 119.3 . . ? C19 C13 C18 124(2) . 3_655 ? C19 C13 C22 119.0(18) . 3_655 ? C18 C13 C22 117.4(17) 3_655 3_655 ? C21 C14 C22 124(3) . . ? C21 C14 H10 118.2 . . ? C22 C14 H10 118.2 . . ? C20 C18 C13 118(2) . 3_655 ? C20 C18 C19 124.3(19) . . ? C13 C18 C19 117.6(17) 3_655 . ? C19 C24 C25 120.0(19) 3_655 . ? C19 C24 H11 120.0 3_655 . ? C25 C24 H11 120.0 . . ? C24 C19 C13 120(2) 3_655 . ? C24 C19 C18 121.0(19) 3_655 . ? C13 C19 C18 118.8(18) . . ? C18 C20 C21 123(2) . . ? C18 C20 H12 118.4 . . ? C21 C20 H12 118.4 . . ? C14 C22 C23 127(2) . . ? C14 C22 C13 117.7(19) . 3_655 ? C23 C22 C13 115.7(18) . 3_655 ? C14 C21 C20 120(2) . . ? C14 C21 H13 120.1 . . ? C20 C21 H13 120.1 . . ? C25 C23 C22 125(2) . . ? C25 C23 H14 117.4 . . ? C22 C23 H14 117.4 . . ? C23 C25 C24 120(2) . . ? C23 C25 H15 120.1 . . ? C24 C25 H15 120.1 . . ? 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 C7 C1 C4 C3 0.3(2) 3_655 . . 3_655 ? C1 C1 C4 C3 179.94(18) 3_655 . . 3_655 ? C7 C1 C4 C6 -179.92(15) 3_655 . . . ? C1 C1 C4 C6 -0.3(3) 3_655 . . . ? C4 C3 C5 C2 -0.1(3) 3_655 . . . ? C10 C3 C5 C2 -179.72(17) . . . . ? C7 C2 C5 C3 -0.3(3) . . . . ? C8 C2 C5 C3 178.69(16) . . . . ? C3 C4 C6 C9 179.94(16) 3_655 . . . ? C1 C4 C6 C9 0.2(3) . . . . ? C5 C2 C7 C1 0.4(2) . . . 3_655 ? C8 C2 C7 C1 -178.58(15) . . . 3_655 ? C5 C2 C7 C9 -179.73(16) . . . . ? C8 C2 C7 C9 1.2(3) . . . . ? C4 C6 C9 C7 -0.1(3) . . . . ? C2 C7 C9 C6 -179.62(16) . . . . ? C1 C7 C9 C6 0.2(3) 3_655 . . . ? C18 C13 C19 C24 -179.7(18) 3_655 . . 3_655 ? C22 C13 C19 C24 0(3) 3_655 . . 3_655 ? C18 C13 C19 C18 0(3) 3_655 . . . ? C22 C13 C19 C18 -179.8(16) 3_655 . . . ? C20 C18 C19 C24 1(3) . . . 3_655 ? C13 C18 C19 C24 179.7(18) 3_655 . . 3_655 ? C20 C18 C19 C13 -178.9(19) . . . . ? C13 C18 C19 C13 0(3) 3_655 . . . ? C13 C18 C20 C21 1(3) 3_655 . . . ? C19 C18 C20 C21 -179.8(18) . . . . ? C21 C14 C22 C23 179(2) . . . . ? C21 C14 C22 C13 -3(3) . . . 3_655 ? C22 C14 C21 C20 3(3) . . . . ? C18 C20 C21 C14 -3(3) . . . . ? C14 C22 C23 C25 -180(2) . . . . ? C13 C22 C23 C25 2(3) 3_655 . . . ? C22 C23 C25 C24 -3(3) . . . . ? C19 C24 C25 C23 3(3) 3_655 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.429 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.057