Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Michael McGlinchey' _publ_contact_author_address ; Chemistry and Chemical Biology University College Dublin Belfield Dublin 4 REPUBLIC OF IRELAND ; _publ_contact_author_email MICHAEL.MCGLINCHEY@UCD.IE _publ_section_title ; Joining the rings: the preparation of 2- and 3-indenyltriptycenes, and curious related processe ; loop_ _publ_author_name 'Michael McGlinchey' 'Helge Muller-Bunz' 'Kirill Nikitin' 'Yannick Ortin' # Attachment 'Compound_7a.cif' data_mjm130_4 _database_code_depnum_ccdc_archive 'CCDC 638735' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Br' _chemical_formula_weight 271.15 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.407(2) _cell_length_b 9.859(2) _cell_length_c 10.146(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.153(6) _cell_angle_gamma 90.00 _cell_volume 1134.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2835 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 30.00 _exptl_crystal_description chunk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 3.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3237 _exptl_absorpt_correction_T_max 0.5338 _exptl_absorpt_process_details TWINABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10468 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5339 _reflns_number_gt 4177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1258P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.164(18) _refine_ls_number_reflns 5339 _refine_ls_number_parameters 290 _refine_ls_number_restraints 88 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1998 _refine_ls_wR_factor_gt 0.1477 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.096 _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 C3 C 0.3136(6) 0.7223(7) 0.5920(6) 0.0174(12) Uani 1 1 d U . . H1 H 0.3564 0.8037 0.5822 0.021 Uiso 1 1 calc R . . C2 C 0.3424(7) 0.6190(8) 0.6827(8) 0.0181(15) Uani 1 1 d U . . C1 C 0.2543(6) 0.5124(7) 0.6732(7) 0.0222(14) Uani 1 1 d U . . H3A H 0.2169 0.5046 0.7565 0.027 Uiso 1 1 calc R . . H3B H 0.2896 0.4239 0.6535 0.027 Uiso 1 1 calc R . . C7A C 0.1657(6) 0.5578(7) 0.5595(7) 0.0178(13) Uani 1 1 d U . . C7 C 0.0649(6) 0.4933(8) 0.5036(7) 0.0216(13) Uani 1 1 d U . . H5 H 0.0417 0.4077 0.5351 0.026 Uiso 1 1 calc R . . C6 C -0.0016(6) 0.5592(8) 0.3987(7) 0.0197(14) Uani 1 1 d U . . H6 H -0.0713 0.5175 0.3580 0.024 Uiso 1 1 calc R . . C5 C 0.0329(7) 0.6861(7) 0.3524(8) 0.0223(14) Uani 1 1 d U . . H7 H -0.0142 0.7296 0.2819 0.027 Uiso 1 1 calc R . . C4 C 0.1333(7) 0.7467(7) 0.4083(7) 0.0243(14) Uani 1 1 d U . . H8 H 0.1566 0.8324 0.3772 0.029 Uiso 1 1 calc R . . C3A C 0.2029(7) 0.6803(8) 0.5135(7) 0.0176(14) Uani 1 1 d U . . C8 C 0.4451(6) 0.6201(6) 0.7865(7) 0.0127(12) Uani 1 1 d U . . C9 C 0.5384(6) 0.7144(7) 0.7801(7) 0.0171(13) Uani 1 1 d U . . H11 H 0.5353 0.7783 0.7097 0.021 Uiso 1 1 calc R . . C10 C 0.6326(6) 0.7132(7) 0.8756(7) 0.0219(14) Uani 1 1 d U . . H12 H 0.6936 0.7779 0.8699 0.026 Uiso 1 1 calc R . . C11 C 0.6433(11) 0.6219(11) 0.9805(13) 0.044(2) Uani 1 1 d U . . C12 C 0.5453(6) 0.5309(7) 0.9904(7) 0.0207(13) Uani 1 1 d U . . H14 H 0.5454 0.4719 1.0644 0.025 Uiso 1 1 calc R . . C13 C 0.4505(6) 0.5296(7) 0.8915(6) 0.0177(13) Uani 1 1 d U . . H15 H 0.3887 0.4657 0.8962 0.021 Uiso 1 1 calc R . . Br1 Br 0.76562(6) 0.62747(9) 1.11431(6) 0.0284(3) Uani 1 1 d U . . C16 C 0.8986(6) 0.7668(7) 0.6689(7) 0.0191(13) Uani 1 1 d U . . H16A H 0.8884 0.6755 0.7065 0.023 Uiso 1 1 calc R . . H16B H 0.9646 0.7644 0.6130 0.023 Uiso 1 1 calc R . . C17 C 0.9188(6) 0.8686(7) 0.7733(7) 0.0125(14) Uani 1 1 d U . . C18 C 0.8328(6) 0.9702(7) 0.7617(7) 0.0192(13) Uani 1 1 d U . . H18 H 0.8285 1.0469 0.8176 0.023 Uiso 1 1 calc R . . C19 C 0.7506(6) 0.9342(8) 0.6459(7) 0.0176(13) Uani 1 1 d U . . C20 C 0.6509(6) 0.9997(7) 0.5882(7) 0.0202(13) Uani 1 1 d U . . H20 H 0.6265 1.0835 0.6226 0.024 Uiso 1 1 calc R . . C21 C 0.5864(7) 0.9395(8) 0.4775(8) 0.0223(14) Uani 1 1 d U . . H21 H 0.5177 0.9837 0.4372 0.027 Uiso 1 1 calc R . . C22 C 0.6207(7) 0.8165(7) 0.4253(8) 0.0217(14) Uani 1 1 d U . . H22 H 0.5746 0.7763 0.3520 0.026 Uiso 1 1 calc R . . C23 C 0.7251(6) 0.7520(7) 0.4828(7) 0.0214(13) Uani 1 1 d U . . H23 H 0.7509 0.6692 0.4477 0.026 Uiso 1 1 calc R . . C24 C 0.7897(7) 0.8135(8) 0.5931(7) 0.0183(13) Uani 1 1 d U . . C25 C 1.0253(6) 0.8673(6) 0.8781(7) 0.0107(11) Uani 1 1 d U . . C26 C 1.1286(6) 0.8035(7) 0.8521(7) 0.0192(13) Uani 1 1 d U . . H26 H 1.1320 0.7557 0.7713 0.023 Uiso 1 1 calc R . . C27 C 1.2266(6) 0.8100(7) 0.9449(7) 0.0209(13) Uani 1 1 d U . . H27 H 1.2996 0.7735 0.9245 0.025 Uiso 1 1 calc R . . C28 C 1.2189(11) 0.8702(10) 1.0692(11) 0.041(2) Uani 1 1 d U . . C29 C 1.1154(6) 0.9380(7) 1.0902(7) 0.0234(14) Uani 1 1 d U . . H29 H 1.1119 0.9888 1.1692 0.028 Uiso 1 1 calc R . . C30 C 1.0187(6) 0.9322(7) 0.9977(7) 0.0192(13) Uani 1 1 d U . . H30 H 0.9468 0.9730 1.0159 0.023 Uiso 1 1 calc R . . Br2 Br 1.35513(5) 0.88412(9) 1.18928(5) 0.0249(2) Uani 1 1 d U . . 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 C3 0.016(3) 0.023(3) 0.013(3) 0.001(2) 0.000(2) 0.000(2) C2 0.018(4) 0.028(4) 0.006(3) -0.004(3) -0.008(3) 0.007(3) C1 0.023(4) 0.020(3) 0.023(3) -0.001(2) -0.003(3) -0.006(3) C7A 0.020(3) 0.022(3) 0.012(3) -0.003(2) 0.005(2) 0.000(3) C7 0.010(3) 0.033(4) 0.021(3) -0.005(3) -0.003(2) 0.001(3) C6 0.009(3) 0.032(4) 0.018(3) 0.001(3) 0.002(2) -0.001(3) C5 0.023(4) 0.017(3) 0.025(4) 0.003(3) -0.003(3) 0.000(3) C4 0.029(4) 0.019(3) 0.025(4) 0.001(3) 0.001(3) 0.005(3) C3A 0.022(4) 0.021(3) 0.009(3) -0.006(3) 0.001(2) -0.001(3) C8 0.011(3) 0.014(3) 0.012(3) -0.004(2) -0.002(2) 0.000(2) C9 0.020(3) 0.015(3) 0.016(3) 0.005(2) 0.001(2) 0.000(2) C10 0.020(3) 0.028(4) 0.018(3) -0.004(3) 0.001(2) -0.007(3) C11 0.039(5) 0.050(6) 0.043(5) 0.009(4) 0.001(4) -0.004(4) C12 0.020(3) 0.021(3) 0.021(3) 0.006(3) -0.001(2) 0.000(2) C13 0.018(3) 0.024(3) 0.012(3) 0.005(2) 0.005(2) 0.002(2) Br1 0.0255(5) 0.0328(5) 0.0245(5) 0.0000(3) -0.0091(4) 0.0008(3) C16 0.021(3) 0.021(3) 0.015(3) 0.003(2) -0.002(2) -0.003(2) C17 0.009(3) 0.020(4) 0.008(3) 0.001(2) -0.004(2) -0.009(2) C18 0.011(3) 0.021(3) 0.025(3) -0.001(3) 0.001(2) 0.000(2) C19 0.014(3) 0.027(4) 0.012(3) 0.000(3) 0.004(2) 0.002(3) C20 0.011(3) 0.028(3) 0.021(3) 0.006(3) -0.003(2) 0.003(2) C21 0.015(3) 0.035(4) 0.017(3) 0.001(3) 0.004(2) 0.010(3) C22 0.026(4) 0.011(3) 0.027(4) 0.002(3) -0.001(3) 0.002(3) C23 0.022(3) 0.022(3) 0.020(3) 0.003(2) -0.001(3) -0.006(3) C24 0.021(3) 0.018(3) 0.015(3) 0.004(3) 0.002(2) -0.002(3) C25 0.010(3) 0.011(3) 0.012(3) 0.002(2) 0.003(2) -0.003(2) C26 0.019(3) 0.023(3) 0.015(3) -0.004(2) 0.001(2) 0.000(3) C27 0.018(3) 0.024(3) 0.021(3) -0.004(3) 0.002(2) -0.001(3) C28 0.049(5) 0.041(6) 0.032(5) 0.004(4) -0.008(4) 0.001(4) C29 0.029(4) 0.028(4) 0.013(3) -0.005(2) 0.001(3) 0.002(3) C30 0.009(3) 0.023(3) 0.024(3) -0.003(3) -0.004(2) 0.002(2) Br2 0.0186(4) 0.0320(4) 0.0224(5) -0.0014(3) -0.0058(3) -0.0011(4) _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 C3 C2 1.388(10) . ? C3 C3A 1.478(10) . ? C3 H1 0.9500 . ? C2 C1 1.450(11) . ? C2 C8 1.489(10) . ? C1 C7A 1.518(10) . ? C1 H3A 0.9900 . ? C1 H3B 0.9900 . ? C7A C3A 1.377(11) . ? C7A C7 1.382(9) . ? C7 C6 1.399(9) . ? C7 H5 0.9500 . ? C6 C5 1.407(10) . ? C6 H6 0.9500 . ? C5 C4 1.361(10) . ? C5 H7 0.9500 . ? C4 C3A 1.420(10) . ? C4 H8 0.9500 . ? C8 C13 1.386(9) . ? C8 C9 1.420(9) . ? C9 C10 1.368(10) . ? C9 H11 0.9500 . ? C10 C11 1.390(13) . ? C10 H12 0.9500 . ? C11 C12 1.445(13) . ? C11 Br1 1.840(13) . ? C12 C13 1.394(10) . ? C12 H14 0.9500 . ? C13 H15 0.9500 . ? C16 C17 1.460(9) . ? C16 C24 1.463(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.398(10) . ? C17 C25 1.526(10) . ? C18 C19 1.466(10) . ? C18 H18 0.9500 . ? C19 C20 1.383(9) . ? C19 C24 1.398(11) . ? C20 C21 1.407(10) . ? C20 H20 0.9500 . ? C21 C22 1.396(11) . ? C21 H21 0.9500 . ? C22 C23 1.419(10) . ? C22 H22 0.9500 . ? C23 C24 1.409(10) . ? C23 H23 0.9500 . ? C25 C30 1.381(9) . ? C25 C26 1.385(9) . ? C26 C27 1.385(9) . ? C26 H26 0.9500 . ? C27 C28 1.405(13) . ? C27 H27 0.9500 . ? C28 C29 1.393(14) . ? C28 Br2 1.874(12) . ? C29 C30 1.371(9) . ? C29 H29 0.9500 . ? C30 H30 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 C2 C3 C3A 106.2(7) . . ? C2 C3 H1 126.9 . . ? C3A C3 H1 126.9 . . ? C3 C2 C1 112.0(7) . . ? C3 C2 C8 125.2(7) . . ? C1 C2 C8 122.6(6) . . ? C2 C1 C7A 103.7(6) . . ? C2 C1 H3A 111.0 . . ? C7A C1 H3A 111.0 . . ? C2 C1 H3B 111.0 . . ? C7A C1 H3B 111.0 . . ? H3A C1 H3B 109.0 . . ? C3A C7A C7 122.5(7) . . ? C3A C7A C1 108.2(6) . . ? C7 C7A C1 129.3(7) . . ? C7A C7 C6 117.3(7) . . ? C7A C7 H5 121.4 . . ? C6 C7 H5 121.4 . . ? C7 C6 C5 121.3(6) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C4 C5 C6 120.3(7) . . ? C4 C5 H7 119.9 . . ? C6 C5 H7 119.9 . . ? C5 C4 C3A 119.2(7) . . ? C5 C4 H8 120.4 . . ? C3A C4 H8 120.4 . . ? C7A C3A C4 119.4(7) . . ? C7A C3A C3 109.8(7) . . ? C4 C3A C3 130.7(7) . . ? C13 C8 C9 119.0(6) . . ? C13 C8 C2 120.4(6) . . ? C9 C8 C2 120.6(6) . . ? C10 C9 C8 119.9(6) . . ? C10 C9 H11 120.1 . . ? C8 C9 H11 120.1 . . ? C9 C10 C11 123.1(8) . . ? C9 C10 H12 118.5 . . ? C11 C10 H12 118.5 . . ? C10 C11 C12 116.7(10) . . ? C10 C11 Br1 122.9(8) . . ? C12 C11 Br1 119.9(8) . . ? C13 C12 C11 120.2(7) . . ? C13 C12 H14 119.9 . . ? C11 C12 H14 119.9 . . ? C8 C13 C12 121.0(6) . . ? C8 C13 H15 119.5 . . ? C12 C13 H15 119.5 . . ? C17 C16 C24 103.0(6) . . ? C17 C16 H16A 111.2 . . ? C24 C16 H16A 111.2 . . ? C17 C16 H16B 111.2 . . ? C24 C16 H16B 111.2 . . ? H16A C16 H16B 109.1 . . ? C18 C17 C16 112.1(6) . . ? C18 C17 C25 124.3(6) . . ? C16 C17 C25 123.5(6) . . ? C17 C18 C19 106.1(6) . . ? C17 C18 H18 127.0 . . ? C19 C18 H18 127.0 . . ? C20 C19 C24 121.2(7) . . ? C20 C19 C18 130.7(7) . . ? C24 C19 C18 108.1(7) . . ? C19 C20 C21 118.5(7) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 121.7(7) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 119.3(7) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 118.6(7) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C19 C24 C23 120.6(7) . . ? C19 C24 C16 110.7(7) . . ? C23 C24 C16 128.6(7) . . ? C30 C25 C26 120.4(6) . . ? C30 C25 C17 119.6(6) . . ? C26 C25 C17 120.0(6) . . ? C27 C26 C25 119.4(6) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 120.5(8) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 118.4(9) . . ? C29 C28 Br2 121.5(8) . . ? C27 C28 Br2 119.2(8) . . ? C30 C29 C28 120.5(7) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C25 120.4(6) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? 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 C3A C3 C2 C1 -2.4(9) . . . . ? C3A C3 C2 C8 -177.4(7) . . . . ? C3 C2 C1 C7A 2.1(8) . . . . ? C8 C2 C1 C7A 177.2(6) . . . . ? C2 C1 C7A C3A -0.9(8) . . . . ? C2 C1 C7A C7 177.8(7) . . . . ? C3A C7A C7 C6 -1.6(10) . . . . ? C1 C7A C7 C6 179.8(7) . . . . ? C7A C7 C6 C5 -0.1(10) . . . . ? C7 C6 C5 C4 0.9(11) . . . . ? C6 C5 C4 C3A 0.1(11) . . . . ? C7 C7A C3A C4 2.6(11) . . . . ? C1 C7A C3A C4 -178.6(6) . . . . ? C7 C7A C3A C3 -179.3(6) . . . . ? C1 C7A C3A C3 -0.5(8) . . . . ? C5 C4 C3A C7A -1.8(11) . . . . ? C5 C4 C3A C3 -179.4(7) . . . . ? C2 C3 C3A C7A 1.8(8) . . . . ? C2 C3 C3A C4 179.6(7) . . . . ? C3 C2 C8 C13 164.2(7) . . . . ? C1 C2 C8 C13 -10.3(10) . . . . ? C3 C2 C8 C9 -15.3(11) . . . . ? C1 C2 C8 C9 170.3(7) . . . . ? C13 C8 C9 C10 1.2(10) . . . . ? C2 C8 C9 C10 -179.4(6) . . . . ? C8 C9 C10 C11 0.6(12) . . . . ? C9 C10 C11 C12 -3.8(14) . . . . ? C9 C10 C11 Br1 -176.1(7) . . . . ? C10 C11 C12 C13 5.3(13) . . . . ? Br1 C11 C12 C13 177.8(6) . . . . ? C9 C8 C13 C12 0.4(10) . . . . ? C2 C8 C13 C12 -179.0(6) . . . . ? C11 C12 C13 C8 -3.7(11) . . . . ? C24 C16 C17 C18 -1.3(8) . . . . ? C24 C16 C17 C25 -178.3(5) . . . . ? C16 C17 C18 C19 0.8(8) . . . . ? C25 C17 C18 C19 177.7(6) . . . . ? C17 C18 C19 C20 -178.9(7) . . . . ? C17 C18 C19 C24 0.2(8) . . . . ? C24 C19 C20 C21 2.4(11) . . . . ? C18 C19 C20 C21 -178.6(7) . . . . ? C19 C20 C21 C22 0.0(11) . . . . ? C20 C21 C22 C23 -1.8(11) . . . . ? C21 C22 C23 C24 1.3(11) . . . . ? C20 C19 C24 C23 -3.0(11) . . . . ? C18 C19 C24 C23 177.9(6) . . . . ? C20 C19 C24 C16 178.1(6) . . . . ? C18 C19 C24 C16 -1.0(8) . . . . ? C22 C23 C24 C19 1.1(10) . . . . ? C22 C23 C24 C16 179.7(7) . . . . ? C17 C16 C24 C19 1.4(8) . . . . ? C17 C16 C24 C23 -177.4(7) . . . . ? C18 C17 C25 C30 26.9(9) . . . . ? C16 C17 C25 C30 -156.4(7) . . . . ? C18 C17 C25 C26 -151.8(7) . . . . ? C16 C17 C25 C26 24.8(9) . . . . ? C30 C25 C26 C27 -2.6(10) . . . . ? C17 C25 C26 C27 176.2(6) . . . . ? C25 C26 C27 C28 5.6(11) . . . . ? C26 C27 C28 C29 -8.1(13) . . . . ? C26 C27 C28 Br2 -177.3(6) . . . . ? C27 C28 C29 C30 7.7(13) . . . . ? Br2 C28 C29 C30 176.6(6) . . . . ? C28 C29 C30 C25 -4.8(11) . . . . ? C26 C25 C30 C29 2.2(10) . . . . ? C17 C25 C30 C29 -176.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.012 _refine_diff_density_min -1.991 _refine_diff_density_rms 0.200 data_mjm132 _database_code_depnum_ccdc_archive 'CCDC 638736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H20' _chemical_formula_weight 368.45 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 11.2911(8) _cell_length_b 8.3652(6) _cell_length_c 20.6135(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.741(2) _cell_angle_gamma 90.00 _cell_volume 1912.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8254 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 31.83 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8531 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20201 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5519 _reflns_number_gt 4817 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.4559P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5519 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.38219(9) 0.09024(12) 0.12696(5) 0.01591(19) Uani 1 1 d . . . H1 H 0.3184(13) 0.0121(18) 0.1294(7) 0.021(3) Uiso 1 1 d . . . C2 C 0.46806(10) 0.05926(13) 0.09070(5) 0.0190(2) Uani 1 1 d . . . H2 H 0.4644(15) -0.044(2) 0.0654(8) 0.034(4) Uiso 1 1 d . . . C3 C 0.56766(10) 0.16908(13) 0.08941(5) 0.0207(2) Uani 1 1 d . . . H3 H 0.6337(14) 0.1322(19) 0.0663(7) 0.027(4) Uiso 1 1 d . . . C4 C 0.57436(9) 0.31331(13) 0.11876(5) 0.0184(2) Uani 1 1 d . . . H4 H 0.6411(14) 0.3851(18) 0.1177(7) 0.025(4) Uiso 1 1 d . . . C4A C 0.47642(9) 0.36828(11) 0.15290(5) 0.01407(18) Uani 1 1 d . . . C4B C 0.39395(9) 0.50572(12) 0.12124(5) 0.01451(19) Uani 1 1 d . . . C5 C 0.36876(9) 0.56641(12) 0.05811(5) 0.0177(2) Uani 1 1 d . . . H5 H 0.4135(13) 0.5282(17) 0.0232(7) 0.021(3) Uiso 1 1 d . . . C6 C 0.27677(10) 0.68141(13) 0.04352(5) 0.0205(2) Uani 1 1 d . . . H6 H 0.2543(14) 0.7239(18) -0.0026(8) 0.026(4) Uiso 1 1 d . . . C7 C 0.21452(10) 0.73412(13) 0.09126(5) 0.0199(2) Uani 1 1 d . . . H7 H 0.1524(14) 0.8166(19) 0.0813(8) 0.028(4) Uiso 1 1 d . . . C8 C 0.24146(9) 0.67340(12) 0.15584(5) 0.0179(2) Uani 1 1 d . . . H8 H 0.1983(13) 0.7135(17) 0.1914(7) 0.019(3) Uiso 1 1 d . . . C8A C 0.33055(9) 0.55880(11) 0.16970(5) 0.01484(19) Uani 1 1 d . . . C9 C 0.37324(9) 0.45649(12) 0.23066(5) 0.01475(19) Uani 1 1 d . . . H9 H 0.3544(12) 0.5018(17) 0.2730(7) 0.018(3) Uiso 1 1 d . . . C10 C 0.32391(9) 0.28864(11) 0.20938(5) 0.01352(19) Uani 1 1 d . . . C10A C 0.38748(9) 0.23663(11) 0.16364(5) 0.01353(18) Uani 1 1 d . . . C11 C 0.50741(9) 0.43383(12) 0.22462(5) 0.01610(19) Uani 1 1 d . . . H11A H 0.5518(13) 0.3526(18) 0.2566(7) 0.023(3) Uiso 1 1 d . . . H11B H 0.5540(13) 0.5343(19) 0.2288(7) 0.023(4) Uiso 1 1 d . . . C12 C 0.30803(9) 0.22893(12) 0.34754(5) 0.0165(2) Uani 1 1 d . . . H12 H 0.3804(13) 0.2752(17) 0.3374(7) 0.018(3) Uiso 1 1 d . . . C13 C 0.29731(10) 0.20807(13) 0.41204(5) 0.0204(2) Uani 1 1 d . . . H13 H 0.3630(15) 0.242(2) 0.4478(8) 0.031(4) Uiso 1 1 d . . . C14 C 0.19268(11) 0.13538(14) 0.42815(5) 0.0232(2) Uani 1 1 d . . . H14 H 0.1871(15) 0.121(2) 0.4746(8) 0.037(4) Uiso 1 1 d . . . C15 C 0.10296(11) 0.08252(14) 0.37954(6) 0.0229(2) Uani 1 1 d . . . H15 H 0.0316(14) 0.0282(19) 0.3901(8) 0.028(4) Uiso 1 1 d . . . C15A C 0.10905(9) 0.10503(12) 0.31143(5) 0.0181(2) Uani 1 1 d . . . C16 C 0.01696(10) 0.05239(13) 0.26126(6) 0.0209(2) Uani 1 1 d . . . H16 H -0.0543(15) -0.005(2) 0.2724(8) 0.032(4) Uiso 1 1 d . . . C16A C 0.01899(9) 0.08345(12) 0.19508(5) 0.0183(2) Uani 1 1 d . . . C17 C -0.07727(10) 0.03264(14) 0.14385(6) 0.0228(2) Uani 1 1 d . . . H17 H -0.1416(15) -0.031(2) 0.1571(8) 0.036(4) Uiso 1 1 d . . . C18 C -0.07779(10) 0.06893(14) 0.07956(6) 0.0230(2) Uani 1 1 d . . . H18 H -0.1418(16) 0.028(2) 0.0437(8) 0.038(4) Uiso 1 1 d . . . C19 C 0.01669(10) 0.16316(14) 0.06244(5) 0.0210(2) Uani 1 1 d . . . H19 H 0.0101(15) 0.1941(19) 0.0144(8) 0.031(4) Uiso 1 1 d . . . C20 C 0.11111(9) 0.21191(12) 0.10971(5) 0.0174(2) Uani 1 1 d . . . H20 H 0.1731(14) 0.2780(17) 0.0967(7) 0.022(3) Uiso 1 1 d . . . C20A C 0.11849(9) 0.16951(12) 0.17771(5) 0.01501(19) Uani 1 1 d . . . C20B C 0.21747(9) 0.21323(11) 0.22763(5) 0.01375(19) Uani 1 1 d . . . C20C C 0.21261(9) 0.18368(12) 0.29478(5) 0.01491(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0177(5) 0.0143(4) 0.0153(4) -0.0001(3) 0.0020(3) -0.0008(3) C2 0.0228(5) 0.0173(5) 0.0174(4) -0.0014(4) 0.0051(4) 0.0019(4) C3 0.0210(5) 0.0223(5) 0.0209(5) 0.0016(4) 0.0092(4) 0.0027(4) C4 0.0162(5) 0.0207(5) 0.0195(5) 0.0027(4) 0.0067(4) -0.0003(4) C4A 0.0139(4) 0.0144(4) 0.0143(4) 0.0007(3) 0.0035(3) -0.0016(3) C4B 0.0139(4) 0.0138(4) 0.0156(4) 0.0001(3) 0.0023(3) -0.0027(3) C5 0.0186(5) 0.0186(5) 0.0160(4) 0.0014(4) 0.0034(3) -0.0028(4) C6 0.0217(5) 0.0199(5) 0.0188(5) 0.0046(4) 0.0009(4) -0.0017(4) C7 0.0184(5) 0.0158(4) 0.0240(5) 0.0020(4) 0.0004(4) -0.0004(4) C8 0.0178(5) 0.0149(4) 0.0207(5) -0.0014(4) 0.0033(4) -0.0016(4) C8A 0.0162(4) 0.0130(4) 0.0152(4) -0.0010(3) 0.0025(3) -0.0033(3) C9 0.0167(4) 0.0140(4) 0.0137(4) -0.0010(3) 0.0031(3) -0.0022(3) C10 0.0146(4) 0.0125(4) 0.0132(4) 0.0009(3) 0.0021(3) -0.0007(3) C10A 0.0135(4) 0.0131(4) 0.0138(4) 0.0010(3) 0.0022(3) -0.0012(3) C11 0.0156(4) 0.0172(4) 0.0149(4) -0.0005(3) 0.0011(3) -0.0030(3) C12 0.0183(5) 0.0163(4) 0.0153(4) 0.0019(3) 0.0038(3) 0.0028(3) C13 0.0237(5) 0.0218(5) 0.0158(5) 0.0023(4) 0.0044(4) 0.0065(4) C14 0.0282(6) 0.0259(5) 0.0176(5) 0.0070(4) 0.0098(4) 0.0083(4) C15 0.0234(5) 0.0252(5) 0.0229(5) 0.0076(4) 0.0117(4) 0.0028(4) C15A 0.0182(5) 0.0181(5) 0.0196(5) 0.0038(4) 0.0074(4) 0.0016(4) C16 0.0174(5) 0.0208(5) 0.0259(5) 0.0040(4) 0.0076(4) -0.0027(4) C16A 0.0152(5) 0.0162(4) 0.0235(5) 0.0010(4) 0.0036(4) -0.0016(3) C17 0.0164(5) 0.0206(5) 0.0305(6) 0.0000(4) 0.0020(4) -0.0044(4) C18 0.0179(5) 0.0214(5) 0.0270(5) -0.0025(4) -0.0027(4) -0.0011(4) C19 0.0191(5) 0.0225(5) 0.0198(5) -0.0002(4) -0.0005(4) 0.0014(4) C20 0.0164(5) 0.0181(4) 0.0173(4) 0.0013(4) 0.0020(3) 0.0006(4) C20A 0.0143(4) 0.0139(4) 0.0169(4) 0.0004(3) 0.0030(3) 0.0004(3) C20B 0.0142(4) 0.0129(4) 0.0146(4) 0.0010(3) 0.0040(3) 0.0006(3) C20C 0.0151(5) 0.0145(4) 0.0158(4) 0.0019(3) 0.0046(3) 0.0022(3) _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 1.3550(14) . ? C1 C10A 1.4346(13) . ? C1 H1 0.981(15) . ? C2 C3 1.4562(15) . ? C2 H2 1.009(17) . ? C3 C4 1.3455(15) . ? C3 H3 1.006(15) . ? C4 C4A 1.4898(14) . ? C4 H4 0.967(15) . ? C4A C10A 1.5340(13) . ? C4A C4B 1.5454(14) . ? C4A C11 1.5544(13) . ? C4B C5 1.3763(13) . ? C4B C8A 1.4050(13) . ? C5 C6 1.4066(15) . ? C5 H5 1.005(14) . ? C6 C7 1.3837(16) . ? C6 H6 1.002(15) . ? C7 C8 1.4041(15) . ? C7 H7 0.978(16) . ? C8 C8A 1.3804(14) . ? C8 H8 1.011(14) . ? C8A C9 1.5226(13) . ? C9 C10 1.5437(13) . ? C9 C11 1.5545(14) . ? C9 H9 1.009(13) . ? C10 C10A 1.3586(13) . ? C10 C20B 1.4670(13) . ? C11 H11A 1.013(15) . ? C11 H11B 0.987(16) . ? C12 C13 1.3684(14) . ? C12 C20C 1.4320(14) . ? C12 H12 0.962(15) . ? C13 C14 1.4219(16) . ? C13 H13 0.985(17) . ? C14 C15 1.3592(17) . ? C14 H14 0.979(17) . ? C15 C15A 1.4308(14) . ? C15 H15 0.985(16) . ? C15A C16 1.3942(15) . ? C15A C20C 1.4379(14) . ? C16 C16A 1.3931(15) . ? C16 H16 1.000(16) . ? C16A C17 1.4316(15) . ? C16A C20A 1.4348(14) . ? C17 C18 1.3584(17) . ? C17 H17 0.977(17) . ? C18 C19 1.4228(16) . ? C18 H18 0.996(17) . ? C19 C20 1.3658(14) . ? C19 H19 1.013(16) . ? C20 C20A 1.4331(14) . ? C20 H20 0.969(15) . ? C20A C20B 1.4188(13) . ? C20B C20C 1.4171(13) . ? 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 C1 C10A 119.35(9) . . ? C2 C1 H1 120.5(8) . . ? C10A C1 H1 120.1(8) . . ? C1 C2 C3 121.60(10) . . ? C1 C2 H2 119.0(9) . . ? C3 C2 H2 119.3(9) . . ? C4 C3 C2 122.43(10) . . ? C4 C3 H3 120.2(9) . . ? C2 C3 H3 117.3(9) . . ? C3 C4 C4A 120.31(9) . . ? C3 C4 H4 121.7(9) . . ? C4A C4 H4 118.0(9) . . ? C4 C4A C10A 114.21(8) . . ? C4 C4A C4B 118.17(8) . . ? C10A C4A C4B 103.64(7) . . ? C4 C4A C11 120.18(8) . . ? C10A C4A C11 98.82(7) . . ? C4B C4A C11 98.64(7) . . ? C5 C4B C8A 120.85(9) . . ? C5 C4B C4A 132.51(9) . . ? C8A C4B C4A 106.36(8) . . ? C4B C5 C6 117.94(10) . . ? C4B C5 H5 121.1(8) . . ? C6 C5 H5 121.0(8) . . ? C7 C6 C5 121.25(10) . . ? C7 C6 H6 119.3(9) . . ? C5 C6 H6 119.4(9) . . ? C6 C7 C8 120.66(10) . . ? C6 C7 H7 121.0(9) . . ? C8 C7 H7 118.3(9) . . ? C8A C8 C7 117.91(10) . . ? C8A C8 H8 120.8(8) . . ? C7 C8 H8 121.3(8) . . ? C8 C8A C4B 121.37(9) . . ? C8 C8A C9 131.88(9) . . ? C4B C8A C9 106.52(8) . . ? C8A C9 C10 103.58(7) . . ? C8A C9 C11 99.54(8) . . ? C10 C9 C11 99.89(8) . . ? C8A C9 H9 114.7(8) . . ? C10 C9 H9 117.6(8) . . ? C11 C9 H9 118.7(8) . . ? C10A C10 C20B 127.17(9) . . ? C10A C10 C9 106.21(8) . . ? C20B C10 C9 125.99(8) . . ? C10 C10A C1 131.58(9) . . ? C10 C10A C4A 108.36(8) . . ? C1 C10A C4A 120.05(8) . . ? C4A C11 C9 93.97(7) . . ? C4A C11 H11A 112.3(8) . . ? C9 C11 H11A 113.7(8) . . ? C4A C11 H11B 113.9(8) . . ? C9 C11 H11B 113.6(9) . . ? H11A C11 H11B 108.9(12) . . ? C13 C12 C20C 120.93(10) . . ? C13 C12 H12 119.7(8) . . ? C20C C12 H12 119.4(8) . . ? C12 C13 C14 120.62(10) . . ? C12 C13 H13 120.0(10) . . ? C14 C13 H13 119.4(10) . . ? C15 C14 C13 120.30(10) . . ? C15 C14 H14 120.5(10) . . ? C13 C14 H14 119.2(10) . . ? C14 C15 C15A 121.00(10) . . ? C14 C15 H15 121.1(9) . . ? C15A C15 H15 117.9(9) . . ? C16 C15A C15 121.38(10) . . ? C16 C15A C20C 119.65(9) . . ? C15 C15A C20C 118.97(10) . . ? C16A C16 C15A 121.42(10) . . ? C16A C16 H16 118.3(9) . . ? C15A C16 H16 120.2(9) . . ? C16 C16A C17 121.22(10) . . ? C16 C16A C20A 119.64(9) . . ? C17 C16A C20A 119.14(10) . . ? C18 C17 C16A 121.20(10) . . ? C18 C17 H17 121.7(10) . . ? C16A C17 H17 117.1(10) . . ? C17 C18 C19 119.91(10) . . ? C17 C18 H18 121.2(10) . . ? C19 C18 H18 118.9(10) . . ? C20 C19 C18 120.67(10) . . ? C20 C19 H19 121.8(9) . . ? C18 C19 H19 117.5(9) . . ? C19 C20 C20A 121.28(10) . . ? C19 C20 H20 118.7(9) . . ? C20A C20 H20 120.0(9) . . ? C20B C20A C20 122.67(9) . . ? C20B C20A C16A 119.73(9) . . ? C20 C20A C16A 117.57(9) . . ? C20C C20B C20A 119.65(9) . . ? C20C C20B C10 120.54(9) . . ? C20A C20B C10 119.81(8) . . ? C20B C20C C12 122.36(9) . . ? C20B C20C C15A 119.62(9) . . ? C12 C20C C15A 118.02(9) . . ? 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 C10A C1 C2 C3 1.68(15) . . . . ? C1 C2 C3 C4 -6.36(17) . . . . ? C2 C3 C4 C4A -1.54(16) . . . . ? C3 C4 C4A C10A 12.31(14) . . . . ? C3 C4 C4A C4B -109.98(11) . . . . ? C3 C4 C4A C11 129.45(11) . . . . ? C4 C4A C4B C5 19.91(16) . . . . ? C10A C4A C4B C5 -107.58(12) . . . . ? C11 C4A C4B C5 151.08(11) . . . . ? C4 C4A C4B C8A -166.30(9) . . . . ? C10A C4A C4B C8A 66.21(9) . . . . ? C11 C4A C4B C8A -35.13(9) . . . . ? C8A C4B C5 C6 -0.78(15) . . . . ? C4A C4B C5 C6 172.27(10) . . . . ? C4B C5 C6 C7 0.99(16) . . . . ? C5 C6 C7 C8 -0.22(16) . . . . ? C6 C7 C8 C8A -0.74(15) . . . . ? C7 C8 C8A C4B 0.95(15) . . . . ? C7 C8 C8A C9 -172.71(10) . . . . ? C5 C4B C8A C8 -0.18(15) . . . . ? C4A C4B C8A C8 -174.85(9) . . . . ? C5 C4B C8A C9 174.90(9) . . . . ? C4A C4B C8A C9 0.23(10) . . . . ? C8 C8A C9 C10 106.52(12) . . . . ? C4B C8A C9 C10 -67.84(9) . . . . ? C8 C8A C9 C11 -150.79(11) . . . . ? C4B C8A C9 C11 34.85(9) . . . . ? C8A C9 C10 C10A 69.20(10) . . . . ? C11 C9 C10 C10A -33.22(9) . . . . ? C8A C9 C10 C20B -102.25(10) . . . . ? C11 C9 C10 C20B 155.33(9) . . . . ? C20B C10 C10A C1 -9.10(17) . . . . ? C9 C10 C10A C1 179.58(10) . . . . ? C20B C10 C10A C4A 170.09(9) . . . . ? C9 C10 C10A C4A -1.23(10) . . . . ? C2 C1 C10A C10 -170.82(11) . . . . ? C2 C1 C10A C4A 10.07(14) . . . . ? C4 C4A C10A C10 164.01(9) . . . . ? C4B C4A C10A C10 -66.07(9) . . . . ? C11 C4A C10A C10 35.13(10) . . . . ? C4 C4A C10A C1 -16.69(13) . . . . ? C4B C4A C10A C1 113.23(9) . . . . ? C11 C4A C10A C1 -145.57(9) . . . . ? C4 C4A C11 C9 -176.65(9) . . . . ? C10A C4A C11 C9 -51.88(8) . . . . ? C4B C4A C11 C9 53.49(8) . . . . ? C8A C9 C11 C4A -53.96(8) . . . . ? C10 C9 C11 C4A 51.75(8) . . . . ? C20C C12 C13 C14 2.33(16) . . . . ? C12 C13 C14 C15 1.42(17) . . . . ? C13 C14 C15 C15A -2.83(17) . . . . ? C14 C15 C15A C16 -179.45(11) . . . . ? C14 C15 C15A C20C 0.55(16) . . . . ? C15 C15A C16 C16A 175.73(10) . . . . ? C20C C15A C16 C16A -4.27(16) . . . . ? C15A C16 C16A C17 -178.42(10) . . . . ? C15A C16 C16A C20A 0.86(16) . . . . ? C16 C16A C17 C18 177.12(11) . . . . ? C20A C16A C17 C18 -2.16(16) . . . . ? C16A C17 C18 C19 -1.92(17) . . . . ? C17 C18 C19 C20 2.92(17) . . . . ? C18 C19 C20 C20A 0.27(17) . . . . ? C19 C20 C20A C20B 177.62(10) . . . . ? C19 C20 C20A C16A -4.25(15) . . . . ? C16 C16A C20A C20B 4.02(15) . . . . ? C17 C16A C20A C20B -176.69(9) . . . . ? C16 C16A C20A C20 -174.16(10) . . . . ? C17 C16A C20A C20 5.13(15) . . . . ? C20 C20A C20B C20C 172.69(9) . . . . ? C16A C20A C20B C20C -5.39(14) . . . . ? C20 C20A C20B C10 -7.28(15) . . . . ? C16A C20A C20B C10 174.64(9) . . . . ? C10A C10 C20B C20C 129.51(11) . . . . ? C9 C10 C20B C20C -60.81(13) . . . . ? C10A C10 C20B C20A -50.52(14) . . . . ? C9 C10 C20B C20A 119.16(10) . . . . ? C20A C20B C20C C12 -178.23(9) . . . . ? C10 C20B C20C C12 1.74(15) . . . . ? C20A C20B C20C C15A 2.00(14) . . . . ? C10 C20B C20C C15A -178.03(9) . . . . ? C13 C12 C20C C20B 175.75(9) . . . . ? C13 C12 C20C C15A -4.48(15) . . . . ? C16 C15A C20C C20B 2.81(15) . . . . ? C15 C15A C20C C20B -177.19(9) . . . . ? C16 C15A C20C C12 -176.96(9) . . . . ? C15 C15A C20C C12 3.04(14) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.557 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.071 # Attachment 'Compound_2.cif' data_mjm143 _database_code_depnum_ccdc_archive 'CCDC 638737' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H20' _chemical_formula_weight 368.45 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 14.876(2) _cell_length_b 10.0507(14) _cell_length_c 12.6706(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1894.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4077 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6722 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12772 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.00 _reflns_number_total 1586 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+1.7783P] 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 1586 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.230 _refine_ls_restrained_S_all 1.230 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.49149(14) 0.0385(2) 0.35655(17) 0.0264(5) Uani 1 1 d . . . H1 H 0.4638 0.0398 0.4241 0.032 Uiso 1 1 calc R . . C2 C 0.55628(15) -0.0562(3) 0.33410(18) 0.0322(6) Uani 1 1 d . . . H2 H 0.5722 -0.1203 0.3860 0.039 Uiso 1 1 calc R . . C3 C 0.59784(16) -0.0581(3) 0.23663(19) 0.0359(6) Uani 1 1 d . . . H3 H 0.6422 -0.1233 0.2215 0.043 Uiso 1 1 calc R . . C4 C 0.57474(15) 0.0354(3) 0.16096(18) 0.0340(6) Uani 1 1 d . . . H4 H 0.6026 0.0335 0.0935 0.041 Uiso 1 1 calc R . . C4A C 0.51132(14) 0.1309(2) 0.18379(17) 0.0279(5) Uani 1 1 d . . . C9 C 0.4013(2) 0.2500 0.2947(2) 0.0237(7) Uani 1 2 d S . . C9A C 0.46687(14) 0.1313(2) 0.28124(16) 0.0238(5) Uani 1 1 d . . . C10 C 0.4892(2) 0.2500 0.1149(2) 0.0299(8) Uani 1 2 d S . . H10 H 0.5229 0.2500 0.0466 0.036 Uiso 1 2 calc SR . . C11 C 0.3882(2) 0.2500 0.0997(2) 0.0250(7) Uani 1 2 d S . . C12 C 0.3408(2) 0.2500 0.1948(2) 0.0240(7) Uani 1 2 d S . . C13 C 0.2480(2) 0.2500 0.1925(2) 0.0246(7) Uani 1 2 d S . . H13 H 0.2150 0.2500 0.2566 0.030 Uiso 1 2 calc SR . . C14 C 0.2030(2) 0.2500 0.0970(3) 0.0292(8) Uani 1 2 d S . . H14 H 0.1392 0.2500 0.0957 0.035 Uiso 1 2 calc SR . . C15 C 0.2508(2) 0.2500 0.0030(3) 0.0310(8) Uani 1 2 d S . . H15 H 0.2197 0.2500 -0.0625 0.037 Uiso 1 2 calc SR . . C16 C 0.3442(2) 0.2500 0.0048(3) 0.0310(8) Uani 1 2 d S . . H16 H 0.3773 0.2500 -0.0594 0.037 Uiso 1 2 calc SR . . C17 C 0.3432(2) 0.2500 0.3929(2) 0.0227(7) Uani 1 2 d S . . C18 C 0.30351(15) 0.1346(3) 0.43837(18) 0.0364(6) Uani 1 1 d P A . H18A H 0.3143 0.0450 0.4183 0.044 Uiso 0.50 1 calc PR A 1 H18B H 0.3505 0.0758 0.4681 0.044 Uiso 0.50 1 calc PR A 2 H18C H 0.2696 0.0844 0.3843 0.044 Uiso 0.50 1 calc PR A 2 C18A C 0.24207(14) 0.1809(2) 0.52316(16) 0.0265(5) Uani 1 1 d . . . C19 C 0.19174(15) 0.1105(3) 0.59743(18) 0.0326(6) Uani 1 1 d . A . H19 H 0.1925 0.0160 0.5986 0.039 Uiso 1 1 calc R . . C20 C 0.14116(15) 0.1810(3) 0.66877(17) 0.0331(6) Uani 1 1 d . . . H20 H 0.1056 0.1345 0.7189 0.040 Uiso 1 1 calc R A . 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 0.0249(12) 0.0346(13) 0.0198(11) -0.0021(10) -0.0020(9) 0.0013(10) C2 0.0325(13) 0.0376(14) 0.0265(12) -0.0037(11) -0.0100(10) 0.0080(11) C3 0.0291(13) 0.0437(15) 0.0350(14) -0.0120(12) -0.0061(11) 0.0152(12) C4 0.0248(12) 0.0527(16) 0.0244(12) -0.0087(12) 0.0036(10) 0.0043(12) C4A 0.0225(12) 0.0371(13) 0.0240(11) -0.0046(11) -0.0026(9) -0.0008(10) C9 0.0210(16) 0.0304(18) 0.0196(16) 0.000 -0.0020(13) 0.000 C9A 0.0190(11) 0.0315(13) 0.0209(11) -0.0021(10) -0.0033(9) -0.0008(10) C10 0.0281(18) 0.043(2) 0.0188(16) 0.000 0.0044(14) 0.000 C11 0.0263(17) 0.0255(17) 0.0233(16) 0.000 0.0007(14) 0.000 C12 0.0268(17) 0.0224(17) 0.0227(17) 0.000 0.0016(14) 0.000 C13 0.0277(17) 0.0219(17) 0.0242(17) 0.000 0.0034(14) 0.000 C14 0.0246(17) 0.0251(17) 0.0378(19) 0.000 -0.0074(15) 0.000 C15 0.039(2) 0.0308(19) 0.0237(17) 0.000 -0.0097(15) 0.000 C16 0.041(2) 0.0315(19) 0.0210(17) 0.000 0.0014(15) 0.000 C17 0.0183(15) 0.0317(18) 0.0182(15) 0.000 -0.0028(13) 0.000 C18 0.0272(12) 0.0583(17) 0.0238(12) 0.0088(12) -0.0002(10) 0.0137(12) C18A 0.0212(11) 0.0396(13) 0.0188(11) 0.0034(10) -0.0020(9) 0.0065(10) C19 0.0342(13) 0.0331(14) 0.0306(13) 0.0051(11) 0.0003(11) 0.0063(11) C20 0.0271(12) 0.0487(14) 0.0234(12) 0.0081(11) 0.0067(10) -0.0040(11) _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 C9A 1.384(3) . ? C1 C2 1.384(3) . ? C1 H1 0.9500 . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C4A 1.377(3) . ? C4 H4 0.9500 . ? C4A C9A 1.401(3) . ? C4A C10 1.518(3) . ? C9 C17 1.514(4) . ? C9 C9A 1.550(3) 7_565 ? C9 C9A 1.550(3) . ? C9 C12 1.555(4) . ? C10 C11 1.514(4) . ? C10 C4A 1.518(3) 7_565 ? C10 H10 1.0000 . ? C11 C16 1.370(4) . ? C11 C12 1.396(4) . ? C12 C13 1.380(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.387(5) . ? C14 H14 0.9500 . ? C15 C16 1.391(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.424(3) . ? C17 C18 1.424(3) 7_565 ? C17 C18 1.424(3) 7_565 ? C18 C18A 1.485(3) . ? C18 H18A 0.9500 . ? C18 H18B 0.9900 . ? C18 H18C 0.9900 . ? C18A C18A 1.389(5) 7_565 ? C18A C19 1.395(3) . ? C19 C20 1.373(3) . ? C19 H19 0.9500 . ? C20 C20 1.388(5) 7_565 ? C20 H20 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 C9A C1 C2 120.4(2) . . ? C9A C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C4A C4 C3 119.8(2) . . ? C4A C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C4A C9A 120.7(2) . . ? C4 C4A C10 125.3(2) . . ? C9A C4A C10 113.7(2) . . ? C17 C9 C9A 116.73(16) . 7_565 ? C17 C9 C9A 116.73(16) . . ? C9A C9 C9A 100.6(2) 7_565 . ? C17 C9 C12 109.8(2) . . ? C9A C9 C12 105.94(17) 7_565 . ? C9A C9 C12 105.94(17) . . ? C1 C9A C4A 118.7(2) . . ? C1 C9A C9 127.5(2) . . ? C4A C9A C9 113.4(2) . . ? C11 C10 C4A 106.76(18) . . ? C11 C10 C4A 106.76(18) . 7_565 ? C4A C10 C4A 104.1(3) . 7_565 ? C11 C10 H10 112.9 . . ? C4A C10 H10 112.9 . . ? C4A C10 H10 112.9 7_565 . ? C16 C11 C12 121.1(3) . . ? C16 C11 C10 125.8(3) . . ? C12 C11 C10 113.1(3) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 C9 126.7(3) . . ? C11 C12 C9 114.2(3) . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 119.5(3) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 C18 109.1(3) . 7_565 ? C18 C17 C18 109.1(3) . 7_565 ? C18 C17 C18 0.0(2) 7_565 7_565 ? C18 C17 C9 124.73(14) . . ? C18 C17 C9 124.73(14) 7_565 . ? C18 C17 C9 124.73(14) 7_565 . ? C17 C18 C18A 107.1(2) . . ? C17 C18 H18A 126.5 . . ? C17 C18 H18B 110.3 . . ? C17 C18 H18C 110.3 . . ? C18A C18 H18A 126.5 . . ? C18A C18 H18B 110.3 . . ? C18A C18 H18C 110.3 . . ? C18A C18A C19 120.48(14) 7_565 . ? C18A C18A C18 108.25(14) 7_565 . ? C19 C18A C18 131.2(2) . . ? C20 C19 C18A 118.4(2) . . ? C20 C19 H19 120.8 . . ? C18A C19 H19 120.8 . . ? C19 C20 C20 121.06(15) . 7_565 ? C19 C20 H20 119.5 . . ? C20 C20 H20 119.5 7_565 . ? 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 C9A C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C4A 0.9(4) . . . . ? C3 C4 C4A C9A -2.8(4) . . . . ? C3 C4 C4A C10 170.9(2) . . . . ? C2 C1 C9A C4A -2.6(3) . . . . ? C2 C1 C9A C9 -175.2(2) . . . . ? C4 C4A C9A C1 3.6(3) . . . . ? C10 C4A C9A C1 -170.8(2) . . . . ? C4 C4A C9A C9 177.2(2) . . . . ? C10 C4A C9A C9 2.8(3) . . . . ? C17 C9 C9A C1 -13.4(3) . . . . ? C9A C9 C9A C1 113.9(2) 7_565 . . . ? C12 C9 C9A C1 -135.9(2) . . . . ? C17 C9 C9A C4A 173.7(2) . . . . ? C9A C9 C9A C4A -59.0(3) 7_565 . . . ? C12 C9 C9A C4A 51.2(2) . . . . ? C4 C4A C10 C11 128.5(3) . . . . ? C9A C4A C10 C11 -57.4(3) . . . . ? C4 C4A C10 C4A -118.8(2) . . . 7_565 ? C9A C4A C10 C4A 55.3(3) . . . 7_565 ? C4A C10 C11 C16 -124.56(16) . . . . ? C4A C10 C11 C16 124.56(16) 7_565 . . . ? C4A C10 C11 C12 55.44(16) . . . . ? C4A C10 C11 C12 -55.44(16) 7_565 . . . ? C16 C11 C12 C13 0.0 . . . . ? C10 C11 C12 C13 180.0 . . . . ? C16 C11 C12 C9 180.0 . . . . ? C10 C11 C12 C9 0.0 . . . . ? C17 C9 C12 C13 0.0 . . . . ? C9A C9 C12 C13 -126.84(15) 7_565 . . . ? C9A C9 C12 C13 126.84(15) . . . . ? C17 C9 C12 C11 180.0 . . . . ? C9A C9 C12 C11 53.16(15) 7_565 . . . ? C9A C9 C12 C11 -53.16(15) . . . . ? C11 C12 C13 C14 0.0 . . . . ? C9 C12 C13 C14 180.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C12 C11 C16 C15 0.0 . . . . ? C10 C11 C16 C15 180.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C9A C9 C17 C18 -157.2(2) 7_565 . . . ? C9A C9 C17 C18 -38.2(4) . . . . ? C12 C9 C17 C18 82.3(3) . . . . ? C9A C9 C17 C18 38.2(4) 7_565 . . 7_565 ? C9A C9 C17 C18 157.2(2) . . . 7_565 ? C12 C9 C17 C18 -82.3(3) . . . 7_565 ? C9A C9 C17 C18 38.2(4) 7_565 . . 7_565 ? C9A C9 C17 C18 157.2(2) . . . 7_565 ? C12 C9 C17 C18 -82.3(3) . . . 7_565 ? C18 C17 C18 C18A -5.3(3) 7_565 . . . ? C18 C17 C18 C18A -5.3(3) 7_565 . . . ? C9 C17 C18 C18A -172.0(2) . . . . ? C17 C18 C18A C18A 3.2(2) . . . 7_565 ? C17 C18 C18A C19 -174.6(2) . . . . ? C18A C18A C19 C20 1.2(3) 7_565 . . . ? C18 C18A C19 C20 178.9(2) . . . . ? C18A C19 C20 C20 -1.2(3) . . . 7_565 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.287 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.044 # Attachment 'compound_9.cif' data_mjm155 _database_code_depnum_ccdc_archive 'CCDC 639736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16' _chemical_formula_weight 292.36 _chemical_absolute_configuration unk 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 Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 23.6218(16) _cell_length_b 23.6218(16) _cell_length_c 4.7492(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2295.0(4) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 18.78 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7956 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6790 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 18.85 _reflns_number_total 1200 _reflns_number_gt 1122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1276P)^2^+1.3048P] 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 1200 _refine_ls_number_parameters 224 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.2088 _refine_ls_wR_factor_gt 0.1986 _refine_ls_goodness_of_fit_ref 1.376 _refine_ls_restrained_S_all 1.338 _refine_ls_shift/su_max 0.303 _refine_ls_shift/su_mean 0.007 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 0.8069(4) 0.0826(4) 0.742(2) 0.044(3) Uani 1 1 d U . . H1 H 0.8224 0.1238 0.8304 0.18(7) Uiso 1 1 calc R . . C2 C 0.8339(4) 0.0448(4) 0.812(3) 0.055(3) Uani 1 1 d U . . H2 H 0.8670 0.0594 0.9522 0.07(3) Uiso 1 1 calc R . . C3 C 0.8123(4) -0.0155(5) 0.677(3) 0.067(3) Uani 1 1 d U . . H3 H 0.8317 -0.0411 0.7239 0.08(3) Uiso 1 1 calc R . . C4 C 0.7651(4) -0.0374(4) 0.483(3) 0.056(3) Uani 1 1 d U . . H4 H 0.7518 -0.0784 0.3958 0.06(3) Uiso 1 1 calc R . . C4A C 0.7329(4) -0.0003(4) 0.400(2) 0.043(2) Uani 1 1 d U . . C4B C 0.7562(4) 0.0611(4) 0.5370(18) 0.032(2) Uani 1 1 d U . . C5 C 0.6823(4) -0.0234(4) 0.204(2) 0.043(2) Uani 1 1 d U . . H5 H 0.6681 -0.0644 0.1150 0.05(2) Uiso 1 1 calc R . . C5A C 0.6522(4) 0.0124(4) 0.1348(17) 0.032(2) Uani 1 1 d U . . C6 C 0.5998(4) -0.0052(4) -0.0531(17) 0.037(2) Uani 1 1 d U . . H6 H 0.5829 -0.0447 -0.1567 0.02(2) Uiso 1 1 calc R . . C7 C 0.5730(4) 0.0336(4) -0.0884(17) 0.038(2) Uani 1 1 d U . . H7 H 0.5378 0.0202 -0.2170 0.013(18) Uiso 1 1 calc R . . C8 C 0.5962(3) 0.0949(4) 0.0627(16) 0.031(2) Uani 1 1 d U . . H8 H 0.5758 0.1205 0.0382 0.000(16) Uiso 1 1 calc R . . C9 C 0.6482(3) 0.1146(4) 0.2411(15) 0.0228(19) Uani 1 1 d U . . C10 C 0.6870(3) 0.1749(3) 0.4194(16) 0.0224(19) Uani 1 1 d U . . H10 H 0.6582 0.1804 0.5578 0.03(2) Uiso 1 1 calc R . . C10A C 0.7270(3) 0.2362(3) 0.2543(17) 0.0202(18) Uani 1 1 d U . . C11 C 0.7050(4) 0.2665(4) 0.0648(14) 0.0209(19) Uani 1 1 d U . . H11 H 0.6595 0.2487 0.0321 0.007(18) Uiso 1 1 calc R . . C12 C 0.7498(4) 0.3223(4) -0.0733(15) 0.026(2) Uani 1 1 d U . . H12 H 0.7355 0.3428 -0.2047 0.006(17) Uiso 1 1 calc R . . C9A C 0.6757(4) 0.0725(4) 0.2780(16) 0.0250(19) Uani 1 1 d U . . C13 C 0.8157(4) 0.3484(4) -0.0206(17) 0.026(2) Uani 1 1 d U . . H13 H 0.8461 0.3876 -0.1137 0.019(19) Uiso 1 1 calc R . . C14 C 0.8383(4) 0.3195(3) 0.1620(15) 0.022(2) Uani 1 1 d U . . H14 H 0.8839 0.3381 0.1942 0.05(3) Uiso 1 1 calc R . . C14A C 0.7936(4) 0.2627(3) 0.2994(15) 0.0193(19) Uani 1 1 d U . . C15 C 0.8065(3) 0.2220(3) 0.5032(17) 0.0216(19) Uani 1 1 d U . . H15A H 0.8279 0.2474 0.6754 0.000(15) Uiso 1 1 calc R . . H15B H 0.8350 0.2072 0.4171 0.06(3) Uiso 1 1 calc R . . C16 C 0.7391(3) 0.1634(3) 0.5733(16) 0.0195(18) Uani 1 1 d U . . H16 H 0.7317 0.1610 0.7813 0.012(17) Uiso 1 1 calc R . . C16A C 0.7262(3) 0.0977(3) 0.4653(18) 0.0242(19) Uani 1 1 d U . . 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 0.025(5) 0.030(5) 0.070(7) 0.029(5) 0.006(4) 0.009(4) C2 0.032(6) 0.035(5) 0.094(8) 0.025(5) 0.003(6) 0.015(5) C3 0.024(6) 0.042(6) 0.124(10) 0.013(6) -0.006(5) 0.008(5) C4 0.045(6) 0.017(5) 0.104(8) 0.008(5) 0.006(5) 0.012(4) C4A 0.029(5) 0.025(5) 0.068(7) 0.017(4) 0.014(4) 0.009(4) C4B 0.030(5) 0.023(4) 0.040(5) 0.012(4) 0.016(4) 0.012(4) C5 0.027(5) 0.024(5) 0.071(7) -0.005(5) 0.013(4) 0.007(4) C5A 0.023(5) 0.025(4) 0.032(5) -0.002(4) 0.009(4) 0.001(4) C6 0.038(5) 0.034(6) 0.023(5) -0.009(5) 0.004(4) 0.005(4) C7 0.022(5) 0.041(5) 0.026(5) 0.001(4) -0.004(5) -0.003(4) C8 0.022(5) 0.036(5) 0.030(5) 0.009(4) 0.005(4) 0.009(4) C9 0.015(4) 0.031(4) 0.012(4) 0.005(4) 0.004(3) 0.004(4) C10 0.022(4) 0.025(4) 0.020(5) 0.000(3) 0.009(3) 0.012(3) C10A 0.020(4) 0.025(4) 0.016(4) -0.001(3) 0.001(4) 0.010(3) C11 0.026(5) 0.029(5) 0.013(4) -0.007(4) 0.001(4) 0.018(4) C12 0.035(5) 0.028(5) 0.019(5) 0.005(4) 0.001(4) 0.019(4) C9A 0.026(5) 0.027(4) 0.016(4) 0.001(4) 0.005(4) 0.009(4) C13 0.038(5) 0.018(5) 0.023(5) 0.001(4) 0.008(4) 0.015(4) C14 0.025(5) 0.019(4) 0.023(5) 0.000(4) 0.007(4) 0.013(4) C14A 0.021(4) 0.022(4) 0.015(4) -0.001(3) 0.003(4) 0.011(4) C15 0.024(4) 0.016(4) 0.025(5) -0.009(4) -0.006(4) 0.010(3) C16 0.019(4) 0.029(4) 0.009(4) -0.003(3) -0.001(3) 0.012(3) C16A 0.012(4) 0.024(4) 0.029(5) 0.005(4) 0.008(4) 0.003(3) _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 1.373(12) . ? C1 C4B 1.425(12) . ? C1 H1 0.9500 . ? C2 C3 1.408(13) . ? C2 H2 0.9500 . ? C3 C4 1.335(14) . ? C3 H3 0.9500 . ? C4 C4A 1.471(12) . ? C4 H4 0.9500 . ? C4A C5 1.397(13) . ? C4A C4B 1.425(12) . ? C4B C16A 1.406(10) . ? C5 C5A 1.388(11) . ? C5 H5 0.9500 . ? C5A C6 1.410(11) . ? C5A C9A 1.414(10) . ? C6 C7 1.358(11) . ? C6 H6 0.9500 . ? C7 C8 1.455(11) . ? C7 H7 0.9500 . ? C8 C9 1.369(10) . ? C8 H8 0.9500 . ? C9 C9A 1.443(10) . ? C9 C10 1.510(11) . ? C10 C10A 1.496(10) . ? C10 C16 1.569(10) . ? C10 H10 1.0000 . ? C10A C14A 1.389(10) . ? C10A C11 1.402(10) . ? C11 C12 1.376(10) . ? C11 H11 0.9500 . ? C12 C13 1.380(10) . ? C12 H12 0.9500 . ? C9A C16A 1.364(11) . ? C13 C14 1.367(10) . ? C13 H13 0.9500 . ? C14 C14A 1.387(9) . ? C14 H14 0.9500 . ? C14A C15 1.498(10) . ? C15 C16 1.535(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C16A 1.513(10) . ? C16 H16 1.0000 . ? 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 C1 C4B 121.1(9) . . ? C2 C1 H1 119.5 . . ? C4B C1 H1 119.5 . . ? C1 C2 C3 119.7(10) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 121.1(9) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C4A 122.2(9) . . ? C3 C4 H4 118.9 . . ? C4A C4 H4 118.9 . . ? C5 C4A C4B 121.4(7) . . ? C5 C4A C4 122.9(8) . . ? C4B C4A C4 115.7(8) . . ? C16A C4B C1 122.5(8) . . ? C16A C4B C4A 117.4(8) . . ? C1 C4B C4A 120.1(7) . . ? C5A C5 C4A 121.3(7) . . ? C5A C5 H5 119.4 . . ? C4A C5 H5 119.4 . . ? C5 C5A C6 127.7(8) . . ? C5 C5A C9A 115.8(7) . . ? C6 C5A C9A 116.4(8) . . ? C7 C6 C5A 121.1(8) . . ? C7 C6 H6 119.5 . . ? C5A C6 H6 119.5 . . ? C6 C7 C8 122.6(8) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C9 C8 C7 118.1(7) . . ? C9 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C8 C9 C9A 118.5(7) . . ? C8 C9 C10 133.3(7) . . ? C9A C9 C10 108.2(6) . . ? C10A C10 C9 114.3(7) . . ? C10A C10 C16 103.9(5) . . ? C9 C10 C16 104.8(5) . . ? C10A C10 H10 111.1 . . ? C9 C10 H10 111.1 . . ? C16 C10 H10 111.1 . . ? C14A C10A C11 119.7(7) . . ? C14A C10A C10 112.4(6) . . ? C11 C10A C10 127.9(6) . . ? C12 C11 C10A 119.3(7) . . ? C12 C11 H11 120.3 . . ? C10A C11 H11 120.3 . . ? C11 C12 C13 119.9(7) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C16A C9A C5A 124.7(7) . . ? C16A C9A C9 112.1(7) . . ? C5A C9A C9 123.2(7) . . ? C14 C13 C12 121.8(7) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C14A 118.9(7) . . ? C13 C14 H14 120.6 . . ? C14A C14 H14 120.6 . . ? C14 C14A C10A 120.4(7) . . ? C14 C14A C15 128.6(6) . . ? C10A C14A C15 110.9(6) . . ? C14A C15 C16 105.6(6) . . ? C14A C15 H15A 110.6 . . ? C16 C15 H15A 110.6 . . ? C14A C15 H15B 110.6 . . ? C16 C15 H15B 110.6 . . ? H15A C15 H15B 108.8 . . ? C16A C16 C15 116.0(6) . . ? C16A C16 C10 104.3(6) . . ? C15 C16 C10 107.0(6) . . ? C16A C16 H16 109.8 . . ? C15 C16 H16 109.8 . . ? C10 C16 H16 109.8 . . ? C9A C16A C4B 119.3(7) . . ? C9A C16A C16 110.6(7) . . ? C4B C16A C16 130.0(7) . . ? 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 C4B C1 C2 C3 1.5(15) . . . . ? C1 C2 C3 C4 -1.2(16) . . . . ? C2 C3 C4 C4A 0.0(16) . . . . ? C3 C4 C4A C5 -178.3(9) . . . . ? C3 C4 C4A C4B 1.0(13) . . . . ? C2 C1 C4B C16A 178.2(8) . . . . ? C2 C1 C4B C4A -0.5(13) . . . . ? C5 C4A C4B C16A -0.1(11) . . . . ? C4 C4A C4B C16A -179.4(8) . . . . ? C5 C4A C4B C1 178.6(8) . . . . ? C4 C4A C4B C1 -0.7(12) . . . . ? C4B C4A C5 C5A -0.5(13) . . . . ? C4 C4A C5 C5A 178.7(8) . . . . ? C4A C5 C5A C6 -178.3(8) . . . . ? C4A C5 C5A C9A -0.6(12) . . . . ? C5 C5A C6 C7 176.5(8) . . . . ? C9A C5A C6 C7 -1.2(11) . . . . ? C5A C6 C7 C8 0.0(12) . . . . ? C6 C7 C8 C9 1.8(11) . . . . ? C7 C8 C9 C9A -2.3(10) . . . . ? C7 C8 C9 C10 176.9(7) . . . . ? C8 C9 C10 C10A -67.7(10) . . . . ? C9A C9 C10 C10A 111.5(6) . . . . ? C8 C9 C10 C16 179.2(7) . . . . ? C9A C9 C10 C16 -1.6(7) . . . . ? C9 C10 C10A C14A -116.1(7) . . . . ? C16 C10 C10A C14A -2.5(8) . . . . ? C9 C10 C10A C11 62.2(9) . . . . ? C16 C10 C10A C11 175.8(7) . . . . ? C14A C10A C11 C12 -0.2(10) . . . . ? C10 C10A C11 C12 -178.4(7) . . . . ? C10A C11 C12 C13 -1.1(10) . . . . ? C5 C5A C9A C16A 2.6(11) . . . . ? C6 C5A C9A C16A -179.4(7) . . . . ? C5 C5A C9A C9 -177.3(7) . . . . ? C6 C5A C9A C9 0.6(10) . . . . ? C8 C9 C9A C16A -178.8(7) . . . . ? C10 C9 C9A C16A 1.8(8) . . . . ? C8 C9 C9A C5A 1.2(10) . . . . ? C10 C9 C9A C5A -178.2(7) . . . . ? C11 C12 C13 C14 1.6(11) . . . . ? C12 C13 C14 C14A -0.6(10) . . . . ? C13 C14 C14A C10A -0.7(10) . . . . ? C13 C14 C14A C15 179.0(7) . . . . ? C11 C10A C14A C14 1.1(11) . . . . ? C10 C10A C14A C14 179.6(6) . . . . ? C11 C10A C14A C15 -178.6(6) . . . . ? C10 C10A C14A C15 -0.2(9) . . . . ? C14 C14A C15 C16 -176.9(7) . . . . ? C10A C14A C15 C16 2.8(8) . . . . ? C14A C15 C16 C16A 111.7(7) . . . . ? C14A C15 C16 C10 -4.2(7) . . . . ? C10A C10 C16 C16A -119.4(6) . . . . ? C9 C10 C16 C16A 0.9(7) . . . . ? C10A C10 C16 C15 4.0(7) . . . . ? C9 C10 C16 C15 124.3(6) . . . . ? C5A C9A C16A C4B -3.4(11) . . . . ? C9 C9A C16A C4B 176.6(7) . . . . ? C5A C9A C16A C16 178.8(7) . . . . ? C9 C9A C16A C16 -1.3(8) . . . . ? C1 C4B C16A C9A -176.7(7) . . . . ? C4A C4B C16A C9A 2.0(10) . . . . ? C1 C4B C16A C16 0.7(12) . . . . ? C4A C4B C16A C16 179.4(7) . . . . ? C15 C16 C16A C9A -117.1(7) . . . . ? C10 C16 C16A C9A 0.2(8) . . . . ? C15 C16 C16A C4B 65.3(10) . . . . ? C10 C16 C16A C4B -177.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 18.85 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.839 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.117