# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name ' Min Shi' _publ_contact_author_email mshi@mail.sioc.ac.cn _publ_author_name 'Min Shi' data_cd21257 _database_code_depnum_ccdc_archive 'CCDC 869056' #TrackingRef '- cd21257.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H21 N' _chemical_formula_weight 359.45 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.2578(8) _cell_length_b 8.2615(4) _cell_length_c 28.7208(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3857.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4630 _cell_measurement_theta_min 5.011 _cell_measurement_theta_max 47.463 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.127 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.78679 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 22051 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3791 _reflns_number_gt 2986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0537P)^2^+0.7527P] 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 SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3791 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.06566(7) 0.39782(14) 0.43035(4) 0.0469(3) Uani 1 1 d . . . C1 C 0.10247(8) 0.54658(17) 0.42614(5) 0.0451(3) Uani 1 1 d . . . C2 C 0.10420(10) 0.6517(2) 0.38873(6) 0.0565(4) Uani 1 1 d . . . H2 H 0.0806 0.6241 0.3603 0.068 Uiso 1 1 calc R . . C3 C 0.14230(11) 0.7991(2) 0.39510(6) 0.0623(5) Uani 1 1 d . . . H3 H 0.1437 0.8735 0.3708 0.075 Uiso 1 1 calc R . . C4 C 0.17874(10) 0.8375(2) 0.43756(7) 0.0619(5) Uani 1 1 d . . . H4 H 0.2043 0.9375 0.4410 0.074 Uiso 1 1 calc R . . C5 C 0.17798(9) 0.73222(18) 0.47436(6) 0.0533(4) Uani 1 1 d . . . H5 H 0.2033 0.7602 0.5022 0.064 Uiso 1 1 calc R . . C6 C 0.13870(8) 0.58157(16) 0.46977(5) 0.0443(3) Uani 1 1 d . . . C7 C 0.12143(8) 0.44652(17) 0.50041(5) 0.0438(3) Uani 1 1 d . . . C8 C 0.07580(9) 0.33987(16) 0.47436(5) 0.0434(3) Uani 1 1 d . . . C9 C 0.03397(10) 0.17990(18) 0.47837(5) 0.0524(4) Uani 1 1 d . . . H9A H -0.0009 0.1760 0.5057 0.063 Uiso 1 1 calc R . . H9B H 0.0737 0.0926 0.4800 0.063 Uiso 1 1 calc R . . C10 C -0.01720(11) 0.1689(2) 0.43374(5) 0.0605(5) Uani 1 1 d . . . H10A H -0.0748 0.1887 0.4406 0.073 Uiso 1 1 calc R . . H10B H -0.0121 0.0619 0.4201 0.073 Uiso 1 1 calc R . . C11 C 0.01564(9) 0.29839(18) 0.39958(5) 0.0469(4) Uani 1 1 d . . . H11 H -0.0305 0.3628 0.3878 0.056 Uiso 1 1 calc R . . C12 C 0.14484(9) 0.42586(18) 0.54950(5) 0.0489(4) Uani 1 1 d . . . C13 C 0.21398(11) 0.5012(2) 0.56861(7) 0.0699(5) Uani 1 1 d . . . H13 H 0.2474 0.5651 0.5498 0.084 Uiso 1 1 calc R . . C14 C 0.23300(15) 0.4816(3) 0.61507(8) 0.0912(7) Uani 1 1 d . . . H14 H 0.2791 0.5331 0.6273 0.109 Uiso 1 1 calc R . . C15 C 0.18527(16) 0.3877(3) 0.64360(7) 0.0920(7) Uani 1 1 d . . . H15 H 0.1986 0.3759 0.6749 0.110 Uiso 1 1 calc R . . C16 C 0.11795(13) 0.3117(3) 0.62564(7) 0.0780(6) Uani 1 1 d . . . H16 H 0.0852 0.2474 0.6447 0.094 Uiso 1 1 calc R . . C17 C 0.09835(10) 0.3302(2) 0.57917(6) 0.0597(4) Uani 1 1 d . . . H17 H 0.0525 0.2768 0.5674 0.072 Uiso 1 1 calc R . . C18 C 0.06247(9) 0.22723(16) 0.35903(5) 0.0427(3) Uani 1 1 d . . . C19 C 0.14638(9) 0.22986(18) 0.35703(5) 0.0515(4) Uani 1 1 d . . . H19 H 0.1758 0.2808 0.3806 0.062 Uiso 1 1 calc R . . C20 C 0.18892(10) 0.1571(2) 0.32006(6) 0.0627(4) Uani 1 1 d . . . H20 H 0.2461 0.1602 0.3195 0.075 Uiso 1 1 calc R . . C21 C 0.14782(11) 0.0831(2) 0.28544(6) 0.0655(5) Uani 1 1 d . . . H21 H 0.1770 0.0341 0.2614 0.079 Uiso 1 1 calc R . . C22 C 0.06092(10) 0.0787(2) 0.28508(5) 0.0554(4) Uani 1 1 d . . . C23 C 0.01733(9) 0.15135(17) 0.32235(5) 0.0455(3) Uani 1 1 d . . . C24 C -0.06941(10) 0.1457(2) 0.32118(5) 0.0560(4) Uani 1 1 d . . . H24 H -0.0995 0.1916 0.3453 0.067 Uiso 1 1 calc R . . C25 C -0.10949(12) 0.0736(2) 0.28501(6) 0.0714(5) Uani 1 1 d . . . H25 H -0.1667 0.0717 0.2847 0.086 Uiso 1 1 calc R . . C26 C -0.06629(13) 0.0028(3) 0.24849(6) 0.0805(6) Uani 1 1 d . . . H26 H -0.0945 -0.0461 0.2241 0.097 Uiso 1 1 calc R . . C27 C 0.01667(13) 0.0052(2) 0.24854(6) 0.0747(6) Uani 1 1 d . . . H27 H 0.0452 -0.0425 0.2240 0.090 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 N1 0.0567(7) 0.0407(6) 0.0433(6) -0.0071(5) 0.0001(5) -0.0103(6) C1 0.0450(8) 0.0396(7) 0.0506(8) -0.0078(6) 0.0086(6) -0.0055(6) C2 0.0598(10) 0.0547(9) 0.0550(9) -0.0009(7) 0.0074(7) -0.0071(8) C3 0.0642(10) 0.0492(9) 0.0734(11) 0.0068(8) 0.0161(9) -0.0070(8) C4 0.0539(9) 0.0436(9) 0.0882(13) -0.0097(9) 0.0163(9) -0.0125(7) C5 0.0428(8) 0.0476(8) 0.0696(10) -0.0167(8) 0.0057(7) -0.0054(7) C6 0.0372(7) 0.0409(7) 0.0547(8) -0.0128(6) 0.0062(6) -0.0008(6) C7 0.0397(7) 0.0422(8) 0.0495(8) -0.0109(6) 0.0009(6) 0.0023(6) C8 0.0464(8) 0.0397(7) 0.0442(8) -0.0059(6) 0.0048(6) 0.0008(6) C9 0.0595(9) 0.0408(8) 0.0568(9) -0.0049(7) 0.0026(7) -0.0075(7) C10 0.0712(11) 0.0625(10) 0.0479(8) -0.0127(7) 0.0110(8) -0.0259(8) C11 0.0495(8) 0.0442(8) 0.0470(8) -0.0096(6) -0.0009(6) -0.0073(7) C12 0.0485(8) 0.0454(8) 0.0528(8) -0.0131(7) -0.0063(7) 0.0112(7) C13 0.0703(11) 0.0618(11) 0.0775(12) -0.0107(9) -0.0220(9) -0.0016(9) C14 0.1055(17) 0.0791(14) 0.0891(14) -0.0135(12) -0.0503(13) -0.0022(13) C15 0.1208(19) 0.0904(16) 0.0650(12) -0.0085(12) -0.0376(13) 0.0161(14) C16 0.0903(14) 0.0866(14) 0.0569(10) 0.0045(10) -0.0091(10) 0.0131(11) C17 0.0596(10) 0.0660(10) 0.0536(9) -0.0040(8) -0.0067(8) 0.0057(8) C18 0.0498(8) 0.0383(7) 0.0399(7) 0.0005(6) -0.0003(6) -0.0036(6) C19 0.0514(9) 0.0523(9) 0.0510(8) -0.0026(7) -0.0026(7) -0.0035(7) C20 0.0510(9) 0.0725(11) 0.0646(10) -0.0029(9) 0.0083(8) 0.0027(8) C21 0.0702(11) 0.0720(11) 0.0544(10) -0.0092(8) 0.0169(8) 0.0053(9) C22 0.0687(10) 0.0543(9) 0.0431(8) -0.0058(7) 0.0050(7) -0.0064(8) C23 0.0549(9) 0.0417(8) 0.0398(7) 0.0005(6) 0.0013(6) -0.0065(6) C24 0.0580(9) 0.0624(10) 0.0476(8) -0.0083(7) 0.0007(7) -0.0122(8) C25 0.0639(11) 0.0893(13) 0.0612(10) -0.0100(10) -0.0066(9) -0.0206(10) C26 0.0927(15) 0.0950(15) 0.0537(10) -0.0227(10) -0.0088(10) -0.0253(12) C27 0.0928(15) 0.0820(13) 0.0492(9) -0.0209(9) 0.0077(9) -0.0137(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 N1 C8 1.3616(17) . ? N1 C1 1.3723(18) . ? N1 C11 1.4551(17) . ? C1 C2 1.382(2) . ? C1 C6 1.414(2) . ? C2 C3 1.378(2) . ? C2 H2 0.9300 . ? C3 C4 1.392(2) . ? C3 H3 0.9300 . ? C4 C5 1.369(2) . ? C4 H4 0.9300 . ? C5 C6 1.4051(19) . ? C5 H5 0.9300 . ? C6 C7 1.448(2) . ? C7 C8 1.3735(19) . ? C7 C12 1.470(2) . ? C8 C9 1.491(2) . ? C9 C10 1.531(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.547(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C18 1.5103(19) . ? C11 H11 0.9800 . ? C12 C17 1.386(2) . ? C12 C13 1.397(2) . ? C13 C14 1.380(3) . ? C13 H13 0.9300 . ? C14 C15 1.369(3) . ? C14 H14 0.9300 . ? C15 C16 1.363(3) . ? C15 H15 0.9300 . ? C16 C17 1.381(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.366(2) . ? C18 C23 1.4287(19) . ? C19 C20 1.402(2) . ? C19 H19 0.9300 . ? C20 C21 1.345(2) . ? C20 H20 0.9300 . ? C21 C22 1.413(2) . ? C21 H21 0.9300 . ? C22 C27 1.410(2) . ? C22 C23 1.417(2) . ? C23 C24 1.412(2) . ? C24 C25 1.363(2) . ? C24 H24 0.9300 . ? C25 C26 1.391(3) . ? C25 H25 0.9300 . ? C26 C27 1.349(3) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? 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 C8 N1 C1 110.11(11) . . ? C8 N1 C11 115.67(11) . . ? C1 N1 C11 134.09(12) . . ? N1 C1 C2 129.81(14) . . ? N1 C1 C6 106.66(12) . . ? C2 C1 C6 123.50(13) . . ? C3 C2 C1 117.46(15) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C2 C3 C4 120.61(16) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 121.81(15) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.64(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 116.97(14) . . ? C5 C6 C7 135.50(14) . . ? C1 C6 C7 107.47(12) . . ? C8 C7 C6 105.53(12) . . ? C8 C7 C12 126.00(13) . . ? C6 C7 C12 128.45(13) . . ? N1 C8 C7 110.22(12) . . ? N1 C8 C9 109.16(12) . . ? C7 C8 C9 140.62(14) . . ? C8 C9 C10 103.64(12) . . ? C8 C9 H9A 111.0 . . ? C10 C9 H9A 111.0 . . ? C8 C9 H9B 111.0 . . ? C10 C9 H9B 111.0 . . ? H9A C9 H9B 109.0 . . ? C9 C10 C11 107.62(12) . . ? C9 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? C9 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N1 C11 C18 113.98(12) . . ? N1 C11 C10 101.41(11) . . ? C18 C11 C10 113.21(12) . . ? N1 C11 H11 109.3 . . ? C18 C11 H11 109.3 . . ? C10 C11 H11 109.3 . . ? C17 C12 C13 116.82(15) . . ? C17 C12 C7 120.96(14) . . ? C13 C12 C7 122.21(15) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 119.32(19) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 122.11(17) . . ? C16 C17 H17 118.9 . . ? C12 C17 H17 118.9 . . ? C19 C18 C23 119.27(13) . . ? C19 C18 C11 121.99(12) . . ? C23 C18 C11 118.72(12) . . ? C18 C19 C20 121.18(14) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C21 C20 C19 120.63(16) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 120.90(15) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C27 C22 C21 121.76(15) . . ? C27 C22 C23 119.32(16) . . ? C21 C22 C23 118.92(14) . . ? C24 C23 C22 117.88(13) . . ? C24 C23 C18 123.04(13) . . ? C22 C23 C18 119.08(14) . . ? C25 C24 C23 120.68(15) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 121.12(17) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C25 119.86(17) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C22 121.14(17) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? 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 C8 N1 C1 C2 -176.72(15) . . . . ? C11 N1 C1 C2 -1.3(3) . . . . ? C8 N1 C1 C6 1.04(15) . . . . ? C11 N1 C1 C6 176.48(14) . . . . ? N1 C1 C2 C3 176.31(15) . . . . ? C6 C1 C2 C3 -1.1(2) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? C4 C5 C6 C7 -175.87(15) . . . . ? N1 C1 C6 C5 -177.81(12) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? N1 C1 C6 C7 -0.23(15) . . . . ? C2 C1 C6 C7 177.70(13) . . . . ? C5 C6 C7 C8 176.29(15) . . . . ? C1 C6 C7 C8 -0.63(15) . . . . ? C5 C6 C7 C12 -2.2(3) . . . . ? C1 C6 C7 C12 -179.12(13) . . . . ? C1 N1 C8 C7 -1.50(16) . . . . ? C11 N1 C8 C7 -177.87(12) . . . . ? C1 N1 C8 C9 178.91(12) . . . . ? C11 N1 C8 C9 2.54(17) . . . . ? C6 C7 C8 N1 1.28(15) . . . . ? C12 C7 C8 N1 179.83(13) . . . . ? C6 C7 C8 C9 -179.32(17) . . . . ? C12 C7 C8 C9 -0.8(3) . . . . ? N1 C8 C9 C10 -11.48(16) . . . . ? C7 C8 C9 C10 169.12(18) . . . . ? C8 C9 C10 C11 15.87(16) . . . . ? C8 N1 C11 C18 -114.52(14) . . . . ? C1 N1 C11 C18 70.2(2) . . . . ? C8 N1 C11 C10 7.47(16) . . . . ? C1 N1 C11 C10 -167.78(15) . . . . ? C9 C10 C11 N1 -14.20(16) . . . . ? C9 C10 C11 C18 108.33(14) . . . . ? C8 C7 C12 C17 -25.2(2) . . . . ? C6 C7 C12 C17 152.98(15) . . . . ? C8 C7 C12 C13 155.13(15) . . . . ? C6 C7 C12 C13 -26.7(2) . . . . ? C17 C12 C13 C14 -1.0(3) . . . . ? C7 C12 C13 C14 178.65(17) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C12 -0.5(3) . . . . ? C13 C12 C17 C16 1.1(2) . . . . ? C7 C12 C17 C16 -178.53(15) . . . . ? N1 C11 C18 C19 12.4(2) . . . . ? C10 C11 C18 C19 -102.89(16) . . . . ? N1 C11 C18 C23 -169.29(12) . . . . ? C10 C11 C18 C23 75.47(17) . . . . ? C23 C18 C19 C20 -1.1(2) . . . . ? C11 C18 C19 C20 177.27(14) . . . . ? C18 C19 C20 C21 0.2(3) . . . . ? C19 C20 C21 C22 0.9(3) . . . . ? C20 C21 C22 C27 178.41(18) . . . . ? C20 C21 C22 C23 -1.1(3) . . . . ? C27 C22 C23 C24 0.4(2) . . . . ? C21 C22 C23 C24 179.91(15) . . . . ? C27 C22 C23 C18 -179.32(15) . . . . ? C21 C22 C23 C18 0.2(2) . . . . ? C19 C18 C23 C24 -178.81(15) . . . . ? C11 C18 C23 C24 2.8(2) . . . . ? C19 C18 C23 C22 0.8(2) . . . . ? C11 C18 C23 C22 -177.56(13) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C18 C23 C24 C25 179.10(16) . . . . ? C23 C24 C25 C26 0.5(3) . . . . ? C24 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 C22 -0.1(3) . . . . ? C21 C22 C27 C26 -179.6(2) . . . . ? C23 C22 C27 C26 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.156 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.027 # Attachment '- cd211217.cif' data_cd211217 _database_code_depnum_ccdc_archive 'CCDC 826603' #TrackingRef '- cd211217.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N' _chemical_formula_weight 309.39 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8435(10) _cell_length_b 9.9731(10) _cell_length_c 10.8542(11) _cell_angle_alpha 97.636(2) _cell_angle_beta 116.238(2) _cell_angle_gamma 111.320(2) _cell_volume 833.58(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2148 _cell_measurement_theta_min 4.469 _cell_measurement_theta_max 54.708 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.269 _exptl_crystal_size_min 0.167 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.54389 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 4571 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3222 _reflns_number_gt 2658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0670P)^2^+0.0641P] 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 SHELXL _refine_ls_extinction_coef 0.028(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3222 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 N1 N 1.00714(13) 1.05343(11) 0.18479(11) 0.0494(3) Uani 1 1 d . . . C1 C 0.99788(16) 0.91126(14) 0.17351(14) 0.0467(3) Uani 1 1 d . . . C2 C 1.11661(18) 0.86861(16) 0.25950(15) 0.0571(4) Uani 1 1 d . . . H2 H 1.2250 0.9417 0.3386 0.069 Uiso 1 1 calc R . . C3 C 1.0686(2) 0.71467(18) 0.22377(18) 0.0668(4) Uani 1 1 d . . . H3 H 1.1447 0.6824 0.2805 0.080 Uiso 1 1 calc R . . C4 C 0.9077(2) 0.60661(17) 0.10388(18) 0.0683(4) Uani 1 1 d . . . H4 H 0.8791 0.5031 0.0808 0.082 Uiso 1 1 calc R . . C5 C 0.79052(19) 0.64807(16) 0.01904(16) 0.0586(4) Uani 1 1 d . . . H5 H 0.6839 0.5735 -0.0612 0.070 Uiso 1 1 calc R . . C6 C 0.83119(16) 0.80317(14) 0.05311(13) 0.0462(3) Uani 1 1 d . . . C7 C 0.74135(16) 0.88758(14) -0.00765(14) 0.0471(3) Uani 1 1 d . . . C8 C 0.85686(17) 1.03954(14) 0.07750(14) 0.0487(3) Uani 1 1 d . . . C9 C 0.87187(19) 1.19561(15) 0.08979(16) 0.0596(4) Uani 1 1 d . . . H9A H 0.7750 1.2000 0.0896 0.072 Uiso 1 1 calc R . . H9B H 0.8784 1.2247 0.0100 0.072 Uiso 1 1 calc R . . C10 C 1.0397(2) 1.29923(16) 0.23723(18) 0.0672(4) Uani 1 1 d . . . H10A H 1.0153 1.3232 0.3123 0.081 Uiso 1 1 calc R . . H10B H 1.1042 1.3947 0.2300 0.081 Uiso 1 1 calc R . . C11 C 1.14400(17) 1.21144(14) 0.27657(15) 0.0532(3) Uani 1 1 d . . . H11 H 1.2245 1.2409 0.2431 0.064 Uiso 1 1 calc R . . C12 C 1.24079(16) 1.23175(14) 0.43637(14) 0.0499(3) Uani 1 1 d . . . C13 C 1.15489(19) 1.18539(17) 0.50697(16) 0.0636(4) Uani 1 1 d . . . H13 H 1.0356 1.1426 0.4554 0.076 Uiso 1 1 calc R . . C14 C 1.2424(2) 1.2013(2) 0.65200(18) 0.0796(5) Uani 1 1 d . . . H14 H 1.1822 1.1693 0.6978 0.096 Uiso 1 1 calc R . . C15 C 1.4171(2) 1.2637(2) 0.72932(19) 0.0829(5) Uani 1 1 d . . . H15 H 1.4761 1.2734 0.8274 0.099 Uiso 1 1 calc R . . C16 C 1.5048(2) 1.3117(2) 0.6623(2) 0.0835(5) Uani 1 1 d . . . H16 H 1.6241 1.3556 0.7153 0.100 Uiso 1 1 calc R . . C17 C 1.41748(18) 1.29582(18) 0.51562(18) 0.0679(4) Uani 1 1 d . . . H17 H 1.4785 1.3285 0.4706 0.081 Uiso 1 1 calc R . . C18 C 0.56696(16) 0.82561(15) -0.13562(14) 0.0504(3) Uani 1 1 d . . . C19 C 0.5200(2) 0.91393(19) -0.21806(17) 0.0666(4) Uani 1 1 d . . . H19 H 0.5993 1.0161 -0.1888 0.080 Uiso 1 1 calc R . . C20 C 0.3588(2) 0.8536(2) -0.3421(2) 0.0794(5) Uani 1 1 d . . . H20 H 0.3309 0.9157 -0.3947 0.095 Uiso 1 1 calc R . . C21 C 0.2399(2) 0.7045(2) -0.38877(19) 0.0782(5) Uani 1 1 d . . . H21 H 0.1320 0.6639 -0.4737 0.094 Uiso 1 1 calc R . . C22 C 0.2815(2) 0.6151(2) -0.3090(2) 0.0776(5) Uani 1 1 d . . . H22 H 0.2008 0.5131 -0.3399 0.093 Uiso 1 1 calc R . . C23 C 0.44118(18) 0.67437(17) -0.18342(18) 0.0650(4) Uani 1 1 d . . . H23 H 0.4657 0.6123 -0.1294 0.078 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 N1 0.0553(6) 0.0388(6) 0.0461(6) 0.0097(4) 0.0237(5) 0.0205(5) C1 0.0577(7) 0.0419(6) 0.0454(7) 0.0151(5) 0.0299(6) 0.0250(6) C2 0.0604(8) 0.0587(8) 0.0512(8) 0.0190(6) 0.0268(7) 0.0309(7) C3 0.0776(10) 0.0657(9) 0.0715(10) 0.0334(8) 0.0378(9) 0.0468(8) C4 0.0869(11) 0.0466(8) 0.0785(11) 0.0267(8) 0.0427(9) 0.0383(8) C5 0.0673(9) 0.0421(7) 0.0594(8) 0.0147(6) 0.0311(7) 0.0237(6) C6 0.0565(7) 0.0415(6) 0.0432(7) 0.0153(5) 0.0285(6) 0.0231(6) C7 0.0560(7) 0.0422(7) 0.0451(7) 0.0152(5) 0.0285(6) 0.0233(6) C8 0.0579(7) 0.0452(7) 0.0466(7) 0.0168(5) 0.0282(6) 0.0269(6) C9 0.0753(9) 0.0448(7) 0.0631(9) 0.0200(6) 0.0366(8) 0.0325(7) C10 0.0798(10) 0.0408(7) 0.0695(10) 0.0134(7) 0.0340(8) 0.0270(7) C11 0.0573(8) 0.0412(7) 0.0541(8) 0.0102(6) 0.0328(7) 0.0149(6) C12 0.0498(7) 0.0375(6) 0.0517(8) 0.0053(5) 0.0282(6) 0.0127(5) C13 0.0559(8) 0.0598(8) 0.0580(9) 0.0095(7) 0.0331(7) 0.0115(6) C14 0.0895(12) 0.0690(10) 0.0602(10) 0.0134(8) 0.0450(9) 0.0151(9) C15 0.0899(13) 0.0683(11) 0.0509(9) 0.0079(8) 0.0222(9) 0.0238(9) C16 0.0546(9) 0.0798(12) 0.0705(11) 0.0004(9) 0.0156(8) 0.0199(8) C17 0.0545(8) 0.0624(9) 0.0688(10) 0.0059(7) 0.0343(8) 0.0147(7) C18 0.0540(7) 0.0519(8) 0.0474(7) 0.0158(6) 0.0282(6) 0.0262(6) C19 0.0640(9) 0.0633(9) 0.0633(9) 0.0254(7) 0.0267(8) 0.0295(7) C20 0.0706(10) 0.0922(13) 0.0694(11) 0.0364(9) 0.0262(9) 0.0441(10) C21 0.0553(9) 0.0943(13) 0.0612(10) 0.0154(9) 0.0195(8) 0.0315(9) C22 0.0550(9) 0.0677(10) 0.0782(11) 0.0103(9) 0.0247(8) 0.0177(8) C23 0.0585(8) 0.0548(8) 0.0685(10) 0.0186(7) 0.0281(8) 0.0227(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 N1 C8 1.3596(17) . ? N1 C1 1.3726(16) . ? N1 C11 1.4639(16) . ? C1 C2 1.3858(19) . ? C1 C6 1.4162(18) . ? C2 C3 1.372(2) . ? C2 H2 0.9300 . ? C3 C4 1.388(2) . ? C3 H3 0.9300 . ? C4 C5 1.363(2) . ? C4 H4 0.9300 . ? C5 C6 1.3987(18) . ? C5 H5 0.9300 . ? C6 C7 1.4487(18) . ? C7 C8 1.3745(18) . ? C7 C18 1.4664(18) . ? C8 C9 1.4908(18) . ? C9 C10 1.530(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.539(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.5041(19) . ? C11 H11 0.9800 . ? C12 C17 1.3771(19) . ? C12 C13 1.3779(19) . ? C13 C14 1.371(2) . ? C13 H13 0.9300 . ? C14 C15 1.363(3) . ? C14 H14 0.9300 . ? C15 C16 1.360(3) . ? C15 H15 0.9300 . ? C16 C17 1.387(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.389(2) . ? C18 C23 1.3940(19) . ? C19 C20 1.376(2) . ? C19 H19 0.9300 . ? C20 C21 1.359(3) . ? C20 H20 0.9300 . ? C21 C22 1.367(3) . ? C21 H21 0.9300 . ? C22 C23 1.376(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 C8 N1 C1 110.12(11) . . ? C8 N1 C11 115.24(11) . . ? C1 N1 C11 134.41(11) . . ? N1 C1 C2 130.71(12) . . ? N1 C1 C6 106.47(11) . . ? C2 C1 C6 122.78(12) . . ? C3 C2 C1 117.63(13) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 120.76(14) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 121.78(14) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.76(14) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 117.24(12) . . ? C5 C6 C7 135.07(12) . . ? C1 C6 C7 107.69(11) . . ? C8 C7 C6 105.21(11) . . ? C8 C7 C18 127.09(12) . . ? C6 C7 C18 127.67(11) . . ? N1 C8 C7 110.50(11) . . ? N1 C8 C9 109.05(11) . . ? C7 C8 C9 140.45(13) . . ? C8 C9 C10 103.29(11) . . ? C8 C9 H9A 111.1 . . ? C10 C9 H9A 111.1 . . ? C8 C9 H9B 111.1 . . ? C10 C9 H9B 111.1 . . ? H9A C9 H9B 109.1 . . ? C9 C10 C11 107.41(11) . . ? C9 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? C9 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N1 C11 C12 112.50(11) . . ? N1 C11 C10 100.50(11) . . ? C12 C11 C10 115.39(12) . . ? N1 C11 H11 109.4 . . ? C12 C11 H11 109.4 . . ? C10 C11 H11 109.4 . . ? C17 C12 C13 118.25(14) . . ? C17 C12 C11 120.87(13) . . ? C13 C12 C11 120.89(12) . . ? C14 C13 C12 121.09(14) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 120.28(16) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 119.66(17) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.50(16) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C12 C17 C16 120.21(15) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C23 116.48(13) . . ? C19 C18 C7 121.49(13) . . ? C23 C18 C7 122.01(12) . . ? C20 C19 C18 121.46(15) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 120.95(17) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 118.98(16) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C23 120.81(16) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C18 121.28(15) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 119.4 . . ? 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 C8 N1 C1 C2 -178.35(13) . . . . ? C11 N1 C1 C2 7.6(2) . . . . ? C8 N1 C1 C6 -0.72(14) . . . . ? C11 N1 C1 C6 -174.76(12) . . . . ? N1 C1 C2 C3 177.91(13) . . . . ? C6 C1 C2 C3 0.6(2) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C1 2.2(2) . . . . ? C4 C5 C6 C7 -178.41(14) . . . . ? N1 C1 C6 C5 179.83(11) . . . . ? C2 C1 C6 C5 -2.30(19) . . . . ? N1 C1 C6 C7 0.29(13) . . . . ? C2 C1 C6 C7 178.16(12) . . . . ? C5 C6 C7 C8 -179.20(15) . . . . ? C1 C6 C7 C8 0.23(14) . . . . ? C5 C6 C7 C18 -1.2(2) . . . . ? C1 C6 C7 C18 178.25(12) . . . . ? C1 N1 C8 C7 0.90(15) . . . . ? C11 N1 C8 C7 176.19(10) . . . . ? C1 N1 C8 C9 -178.55(11) . . . . ? C11 N1 C8 C9 -3.25(15) . . . . ? C6 C7 C8 N1 -0.67(14) . . . . ? C18 C7 C8 N1 -178.71(11) . . . . ? C6 C7 C8 C9 178.50(16) . . . . ? C18 C7 C8 C9 0.5(3) . . . . ? N1 C8 C9 C10 -10.46(15) . . . . ? C7 C8 C9 C10 170.36(17) . . . . ? C8 C9 C10 C11 19.59(16) . . . . ? C8 N1 C11 C12 138.43(12) . . . . ? C1 N1 C11 C12 -47.75(18) . . . . ? C8 N1 C11 C10 15.15(14) . . . . ? C1 N1 C11 C10 -171.03(14) . . . . ? C9 C10 C11 N1 -20.71(15) . . . . ? C9 C10 C11 C12 -141.97(12) . . . . ? N1 C11 C12 C17 126.85(14) . . . . ? C10 C11 C12 C17 -118.64(15) . . . . ? N1 C11 C12 C13 -52.53(17) . . . . ? C10 C11 C12 C13 61.99(17) . . . . ? C17 C12 C13 C14 -0.5(2) . . . . ? C11 C12 C13 C14 178.87(15) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 -0.8(3) . . . . ? C13 C12 C17 C16 0.3(2) . . . . ? C11 C12 C17 C16 -179.04(14) . . . . ? C15 C16 C17 C12 0.3(3) . . . . ? C8 C7 C18 C19 24.2(2) . . . . ? C6 C7 C18 C19 -153.45(14) . . . . ? C8 C7 C18 C23 -157.63(14) . . . . ? C6 C7 C18 C23 24.8(2) . . . . ? C23 C18 C19 C20 -1.4(2) . . . . ? C7 C18 C19 C20 176.92(14) . . . . ? C18 C19 C20 C21 -0.4(3) . . . . ? C19 C20 C21 C22 1.2(3) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C21 C22 C23 C18 -1.6(3) . . . . ? C19 C18 C23 C22 2.4(2) . . . . ? C7 C18 C23 C22 -175.92(14) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.178 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.050