# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef 'anti-cumulene_from_m-xylene.cif' _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _publ_contact_author 'Qian Miao' _publ_contact_author_email miaoqian@cuhk.edu.hk _publ_contact_author_name 'Qian Miao' loop_ _publ_author_name 'H. Xia' 'D. Liu' 'K. Song' 'Q. Miao' data_anti-cumulene_from_m-xylene _database_code_depnum_ccdc_archive 'CCDC 823689' _audit_creation_method SHELXL-97 _chemical_name_systematic ; anti-5,5'-(1,2-ethenediylidene)bis-5H-dibenzo[a,d]cycloheptene and m-xylene ; _chemical_name_common ;anti-5,5'-(1,2-ethenediylidene)bis-5H- dibenzo(a,d)cycloheptene and m-xylene ; _chemical_melting_point ? _chemical_formula_moiety 3(C32H20),(C8H10) _chemical_formula_sum C104H70 _chemical_formula_weight 1319.67 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 22.054(4) _cell_length_b 22.054(4) _cell_length_c 13.223(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5570(2) _cell_formula_units_Z 3 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 74 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2082 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6010 _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 8977 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2239 _reflns_number_gt 1269 _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^)+(0.1134P)^2^+1.1955P] 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 2239 _refine_ls_number_parameters 163 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.2087 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.005 _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 0.50391(15) 0.49159(15) 0.04403(18) 0.0515(8) Uani 1 1 d . . . C2 C 0.51016(13) 0.47518(14) 0.13967(18) 0.0456(7) Uani 1 1 d . . . C3 C 0.51965(15) 0.52609(16) 0.22064(19) 0.0513(8) Uani 1 1 d . . . C4 C 0.56212(19) 0.59731(18) 0.1996(3) 0.0690(10) Uani 1 1 d . . . H4A H 0.5833 0.6113 0.1365 0.083 Uiso 1 1 calc R . . C5 C 0.5731(2) 0.6475(2) 0.2719(3) 0.0924(13) Uani 1 1 d . . . H5A H 0.6013 0.6948 0.2566 0.111 Uiso 1 1 calc R . . C6 C 0.5430(3) 0.6281(3) 0.3645(3) 0.1038(15) Uani 1 1 d . . . H6A H 0.5518 0.6618 0.4135 0.125 Uiso 1 1 calc R . . C7 C 0.4995(2) 0.5585(3) 0.3856(3) 0.0874(12) Uani 1 1 d . . . H7A H 0.4774 0.5458 0.4482 0.105 Uiso 1 1 calc R . . C8 C 0.48737(18) 0.50610(18) 0.3153(2) 0.0620(9) Uani 1 1 d . . . C9 C 0.4406(2) 0.4334(2) 0.3459(2) 0.0781(11) Uani 1 1 d . . . H9A H 0.4062 0.4265 0.3926 0.094 Uiso 1 1 calc R . . C10 C 0.4406(2) 0.3753(2) 0.3155(2) 0.0759(11) Uani 1 1 d . . . H10A H 0.4065 0.3338 0.3448 0.091 Uiso 1 1 calc R . . C11 C 0.48613(16) 0.36820(16) 0.2437(2) 0.0576(9) Uani 1 1 d . . . C12 C 0.4978(2) 0.31151(18) 0.2564(3) 0.0758(11) Uani 1 1 d . . . H12A H 0.4773 0.2815 0.3110 0.091 Uiso 1 1 calc R . . C13 C 0.5386(2) 0.2992(2) 0.1909(3) 0.0874(12) Uani 1 1 d . . . H13A H 0.5466 0.2623 0.2027 0.105 Uiso 1 1 calc R . . C14 C 0.5674(2) 0.3411(2) 0.1084(3) 0.0806(11) Uani 1 1 d . . . H14A H 0.5938 0.3320 0.0625 0.097 Uiso 1 1 calc R . . C15 C 0.55683(18) 0.39723(17) 0.0936(2) 0.0650(9) Uani 1 1 d . . . H15A H 0.5766 0.4254 0.0371 0.078 Uiso 1 1 calc R . . C16 C 0.51769(15) 0.41323(15) 0.16038(18) 0.0490(8) Uani 1 1 d . . . C17 C 0.5991(5) 0.3104(7) -0.1677(11) 0.279(7) Uani 1 1 d DU . . C18 C 0.5238(5) 0.2844(13) -0.1531(18) 0.201(9) Uani 0.33 1 d PDU . . 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 0.0460(18) 0.0506(19) 0.0482(13) 0.0053(12) -0.0008(12) 0.0169(15) C2 0.0396(16) 0.0462(17) 0.0429(13) 0.0068(11) -0.0012(11) 0.0153(14) C3 0.0521(19) 0.055(2) 0.0505(15) 0.0031(13) -0.0085(13) 0.0295(16) C4 0.077(3) 0.055(2) 0.076(2) 0.0034(17) -0.0097(17) 0.034(2) C5 0.115(4) 0.056(2) 0.111(3) -0.012(2) -0.023(3) 0.046(2) C6 0.154(5) 0.092(4) 0.094(3) -0.029(3) -0.024(3) 0.082(4) C7 0.118(4) 0.105(3) 0.068(2) -0.010(2) 0.002(2) 0.076(3) C8 0.073(2) 0.074(2) 0.0497(16) -0.0016(15) -0.0039(14) 0.045(2) C9 0.078(3) 0.094(3) 0.0568(18) 0.0120(18) 0.0210(17) 0.039(2) C10 0.077(3) 0.066(2) 0.0612(19) 0.0172(17) 0.0136(17) 0.017(2) C11 0.061(2) 0.0462(19) 0.0507(15) 0.0051(13) -0.0067(14) 0.0158(16) C12 0.089(3) 0.050(2) 0.073(2) 0.0129(16) -0.0089(19) 0.023(2) C13 0.101(3) 0.065(3) 0.104(3) 0.003(2) -0.011(2) 0.047(2) C14 0.087(3) 0.070(3) 0.095(3) -0.003(2) 0.004(2) 0.048(2) C15 0.065(2) 0.059(2) 0.0647(18) 0.0037(15) 0.0022(15) 0.0261(18) C16 0.0454(18) 0.0444(17) 0.0447(13) 0.0001(12) -0.0082(12) 0.0131(14) C17 0.327(9) 0.341(12) 0.079(3) -0.007(4) -0.004(9) 0.101(8) C18 0.180(12) 0.237(13) 0.155(12) 0.001(9) -0.030(9) 0.079(9) _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 C1 1.260(5) 10_665 ? C1 C2 1.341(3) . ? C2 C16 1.482(4) . ? C2 C3 1.489(4) . ? C3 C4 1.397(4) . ? C3 C8 1.398(4) . ? C4 C5 1.389(5) . ? C5 C6 1.357(6) . ? C6 C7 1.372(6) . ? C7 C8 1.401(5) . ? C8 C9 1.465(5) . ? C9 C10 1.343(5) . ? C10 C11 1.447(5) . ? C11 C12 1.407(5) . ? C11 C16 1.411(4) . ? C12 C13 1.369(5) . ? C13 C14 1.364(5) . ? C14 C15 1.382(5) . ? C15 C16 1.397(4) . ? C17 C17 1.312(9) 17_554 ? C17 C17 1.312(9) 18_544 ? C17 C18 1.473(9) . ? 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 C1 C2 176.9(4) 10_665 . ? C1 C2 C16 119.8(3) . . ? C1 C2 C3 118.0(3) . . ? C16 C2 C3 121.6(2) . . ? C4 C3 C8 118.8(3) . . ? C4 C3 C2 117.9(3) . . ? C8 C3 C2 123.3(3) . . ? C5 C4 C3 120.8(3) . . ? C6 C5 C4 120.4(4) . . ? C5 C6 C7 119.7(4) . . ? C6 C7 C8 121.7(4) . . ? C3 C8 C7 118.5(3) . . ? C3 C8 C9 124.2(3) . . ? C7 C8 C9 117.3(3) . . ? C10 C9 C8 128.8(3) . . ? C9 C10 C11 129.1(3) . . ? C12 C11 C16 118.3(3) . . ? C12 C11 C10 117.6(3) . . ? C16 C11 C10 124.2(3) . . ? C13 C12 C11 122.0(3) . . ? C14 C13 C12 120.0(4) . . ? C13 C14 C15 119.3(4) . . ? C14 C15 C16 122.6(3) . . ? C15 C16 C11 117.7(3) . . ? C15 C16 C2 119.0(2) . . ? C11 C16 C2 123.3(3) . . ? C17 C17 C17 119.96(10) 17_554 18_544 ? C17 C17 C18 120.0(7) 17_554 . ? C17 C17 C18 119.1(7) 18_544 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.388 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.042 # Attachment 'syn-cumulene-from-EtOAc.cif' data_syn-cumulene_from_EtOAc _database_code_depnum_ccdc_archive 'CCDC 823690' _audit_creation_method SHELXL-97 _chemical_name_systematic ; syn-5,5'-(1,2-ethenediylidene)bis-5H-dibenzo[a,d]cycloheptene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H20' _chemical_formula_weight 404.48 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.0144(5) _cell_length_b 20.9765(11) _cell_length_c 12.7099(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2136.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 134 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6601 _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 18545 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1983 _reflns_number_gt 1487 _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^)+(0.0558P)^2^+0.8819P] 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 0.0060(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1983 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1474 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 -0.2629(3) 0.28117(17) 0.29162(17) 0.126(2) Uani 1 1 d . . . H1 H -0.3462 0.2996 0.2508 0.151 Uiso 1 1 calc R . . C2 C -0.1545(3) 0.32652(17) 0.34469(17) 0.0897(10) Uani 1 1 d . . . C3 C -0.1522(5) 0.3898(2) 0.3058(3) 0.1274(17) Uani 1 1 d . . . H3A H -0.2196 0.4001 0.2487 0.153 Uiso 1 1 calc R . . C4 C -0.0560(6) 0.4356(2) 0.3485(3) 0.1333(17) Uani 1 1 d . . . H4A H -0.0554 0.4762 0.3193 0.160 Uiso 1 1 calc R . . C5 C 0.0414(4) 0.42273(13) 0.4349(2) 0.0975(10) Uani 1 1 d . . . H5A H 0.1066 0.4545 0.4651 0.117 Uiso 1 1 calc R . . C6 C 0.0407(3) 0.36194(11) 0.47599(18) 0.0701(7) Uani 1 1 d . . . H6A H 0.1069 0.3533 0.5343 0.084 Uiso 1 1 calc R . . C7 C -0.0556(2) 0.31292(12) 0.43343(15) 0.0629(6) Uani 1 1 d . . . C8 C -0.0487(3) 0.2500 0.48675(19) 0.0544(7) Uani 1 2 d S . . C9 C -0.0126(3) 0.2500 0.5900(2) 0.0502(7) Uani 1 2 d S . . C10 C 0.0233(3) 0.2500 0.68550(19) 0.0487(6) Uani 1 2 d S . . C11 C 0.0590(3) 0.2500 0.78841(18) 0.0451(6) Uani 1 2 d S . . C12 C 0.0853(2) 0.31198(9) 0.84113(14) 0.0496(5) Uani 1 1 d . . . C13 C 0.1748(3) 0.35874(10) 0.78763(18) 0.0635(6) Uani 1 1 d . . . H13A H 0.2212 0.3490 0.7225 0.076 Uiso 1 1 calc R . . C14 C 0.1967(3) 0.41898(11) 0.8283(2) 0.0858(8) Uani 1 1 d . . . H14A H 0.2579 0.4493 0.7914 0.103 Uiso 1 1 calc R . . C15 C 0.1263(4) 0.43381(14) 0.9247(3) 0.0993(10) Uani 1 1 d . . . H15A H 0.1376 0.4746 0.9523 0.119 Uiso 1 1 calc R . . C16 C 0.0411(3) 0.38868(14) 0.9788(2) 0.0856(8) Uani 1 1 d . . . H16A H -0.0054 0.3995 1.0434 0.103 Uiso 1 1 calc R . . C17 C 0.0201(2) 0.32654(11) 0.94148(15) 0.0609(6) Uani 1 1 d . . . C18 C -0.0689(3) 0.28163(11) 1.00754(16) 0.0723(7) Uani 1 1 d . . . H18 H -0.1372 0.3002 1.0582 0.087 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 0.0519(12) 0.284(7) 0.0413(11) 0.0200(17) -0.0039(9) 0.0297(19) C2 0.0564(13) 0.173(3) 0.0393(11) 0.0262(15) 0.0108(10) 0.0465(16) C3 0.094(3) 0.222(5) 0.066(2) 0.062(3) 0.0246(17) 0.086(3) C4 0.136(3) 0.154(4) 0.110(3) 0.073(3) 0.051(3) 0.087(3) C5 0.113(2) 0.0846(18) 0.095(2) 0.0303(16) 0.0358(17) 0.0378(16) C6 0.0736(15) 0.0782(16) 0.0586(13) 0.0138(12) 0.0119(11) 0.0221(13) C7 0.0478(11) 0.1025(17) 0.0383(10) 0.0131(11) 0.0104(8) 0.0237(12) C8 0.0393(14) 0.090(2) 0.0335(13) 0.000 0.0036(11) 0.000 C9 0.0466(14) 0.0639(17) 0.0403(15) 0.000 0.0019(11) 0.000 C10 0.0484(14) 0.0610(17) 0.0367(14) 0.000 -0.0002(11) 0.000 C11 0.0400(13) 0.0591(16) 0.0362(13) 0.000 -0.0026(10) 0.000 C12 0.0452(9) 0.0595(12) 0.0440(10) -0.0026(9) -0.0113(8) 0.0086(9) C13 0.0639(13) 0.0596(13) 0.0668(13) 0.0040(10) -0.0125(10) 0.0025(10) C14 0.0860(18) 0.0553(14) 0.116(2) 0.0014(15) -0.0222(17) 0.0021(13) C15 0.100(2) 0.0689(18) 0.129(3) -0.0339(18) -0.030(2) 0.0178(16) C16 0.0808(17) 0.094(2) 0.0824(18) -0.0366(16) -0.0182(14) 0.0259(15) C17 0.0527(11) 0.0798(14) 0.0504(12) -0.0151(11) -0.0147(9) 0.0167(10) C18 0.0579(12) 0.117(2) 0.0415(11) -0.0092(11) -0.0001(9) 0.0108(12) _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 C1 1.308(7) 7_565 ? C1 C2 1.454(4) . ? C2 C7 1.408(3) . ? C2 C3 1.417(5) . ? C3 C4 1.345(6) . ? C4 C5 1.374(5) . ? C5 C6 1.378(3) . ? C6 C7 1.395(3) . ? C7 C8 1.485(2) . ? C8 C9 1.344(4) . ? C8 C7 1.485(2) 7_565 ? C9 C10 1.247(3) . ? C10 C11 1.339(3) . ? C11 C12 1.478(2) 7_565 ? C11 C12 1.478(2) . ? C12 C13 1.392(3) . ? C12 C17 1.412(3) . ? C13 C14 1.376(3) . ? C14 C15 1.385(4) . ? C15 C16 1.355(4) . ? C16 C17 1.397(3) . ? C17 C18 1.450(3) . ? C18 C18 1.327(5) 7_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 C1 C1 C2 130.86(16) 7_565 . ? C7 C2 C3 117.5(3) . . ? C7 C2 C1 125.1(3) . . ? C3 C2 C1 117.3(3) . . ? C4 C3 C2 122.4(3) . . ? C3 C4 C5 120.5(4) . . ? C4 C5 C6 118.8(4) . . ? C5 C6 C7 122.5(2) . . ? C6 C7 C2 118.2(2) . . ? C6 C7 C8 117.26(19) . . ? C2 C7 C8 124.5(3) . . ? C9 C8 C7 116.98(12) . 7_565 ? C9 C8 C7 116.98(12) . . ? C7 C8 C7 125.5(2) 7_565 . ? C10 C9 C8 179.1(3) . . ? C9 C10 C11 179.0(3) . . ? C10 C11 C12 118.26(11) . 7_565 ? C10 C11 C12 118.26(11) . . ? C12 C11 C12 123.2(2) 7_565 . ? C13 C12 C17 118.66(19) . . ? C13 C12 C11 118.16(19) . . ? C17 C12 C11 123.16(19) . . ? C14 C13 C12 121.9(2) . . ? C13 C14 C15 119.1(3) . . ? C16 C15 C14 119.8(2) . . ? C15 C16 C17 122.7(3) . . ? C16 C17 C12 117.6(2) . . ? C16 C17 C18 118.0(2) . . ? C12 C17 C18 124.4(2) . . ? C18 C18 C17 130.53(12) 7_565 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.030