# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jin Liu' 'Elisia M. Murray' 'Young Junior,Victor G. ' _publ_contact_author_name 'Dr Jin Liu' _publ_contact_author_address ; Department of Chemistry Murray State University 456 Blackburn Science Building Murray KY 42071 UNITED STATES OF AMERICA ; _publ_contact_author_email JIN.LIU@MURRAYSTATE.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; ð Stacking interactions in some crystalline cisoid E,E-1,4-diaryl-1,3-butadienes ; data_02258a _database_code_CSD 203757 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 02258a _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H10 F10' _chemical_formula_weight 452.29 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' F F 0.0171 0.0103 '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 9.1151(11) _cell_length_b 9.1761(11) _cell_length_c 11.3748(14) _cell_angle_alpha 69.683(2) _cell_angle_beta 78.016(2) _cell_angle_gamma 84.341(2) _cell_volume 872.40(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3041 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.53 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9462 _exptl_absorpt_correction_T_max 0.9709 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details 'Jin Liu - Murray State University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-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 9725 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3926 _reflns_number_gt 3253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0524P)^2^+0.2114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3926 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.29292(15) 0.01687(15) 0.38994(13) 0.0252(3) Uani 1 1 d . . . C2 C 0.24710(15) 0.17605(15) 0.31235(13) 0.0249(3) Uani 1 1 d . . . C3 C 0.27332(16) 0.17424(16) 0.17748(13) 0.0290(3) Uani 1 1 d . . . H3A H 0.2172 0.2567 0.1183 0.035 Uiso 1 1 calc R . . C4 C 0.44500(17) 0.16678(18) 0.13131(14) 0.0339(3) Uani 1 1 d . . . H4A H 0.4952 0.2462 0.1484 0.041 Uiso 1 1 calc R . . H4B H 0.4698 0.1825 0.0389 0.041 Uiso 1 1 calc R . . C5 C 0.49173(17) 0.00047(18) 0.21083(14) 0.0337(3) Uani 1 1 d . . . H5A H 0.5368 -0.0606 0.1550 0.040 Uiso 1 1 calc R . . H5B H 0.5643 0.0035 0.2636 0.040 Uiso 1 1 calc R . . C6 C 0.34213(16) -0.06841(16) 0.29509(14) 0.0297(3) Uani 1 1 d . . . H6A H 0.3414 -0.1844 0.3324 0.036 Uiso 1 1 calc R . . C7 C 0.23260(18) 0.00632(17) 0.20225(15) 0.0339(3) Uani 1 1 d . . . H7A H 0.2572 -0.0231 0.1244 0.041 Uiso 1 1 calc R . . H7B H 0.1264 -0.0152 0.2433 0.041 Uiso 1 1 calc R . . C8 C 0.28120(15) -0.03504(16) 0.51664(13) 0.0264(3) Uani 1 1 d . . . H8A H 0.2468 0.0388 0.5584 0.032 Uiso 1 1 calc R . . C9 C 0.31512(15) -0.19246(16) 0.59891(13) 0.0253(3) Uani 1 1 d . . . C10 C 0.43731(15) -0.28613(16) 0.57141(13) 0.0258(3) Uani 1 1 d . . . F10 F 0.53898(9) -0.23312(10) 0.46464(8) 0.0329(2) Uani 1 1 d . . . C11 C 0.46163(16) -0.43471(16) 0.65219(14) 0.0300(3) Uani 1 1 d . . . F11 F 0.58060(10) -0.52021(10) 0.62010(9) 0.0404(2) Uani 1 1 d . . . C12 C 0.36346(18) -0.49444(16) 0.76563(14) 0.0327(3) Uani 1 1 d . . . F12 F 0.38414(13) -0.63939(10) 0.84261(9) 0.0473(3) Uani 1 1 d . . . C13 C 0.24306(17) -0.40447(17) 0.79858(13) 0.0309(3) Uani 1 1 d . . . F13 F 0.14569(11) -0.46294(12) 0.90767(8) 0.0429(2) Uani 1 1 d . . . C14 C 0.22116(15) -0.25643(17) 0.71657(13) 0.0280(3) Uani 1 1 d . . . F14 F 0.10152(10) -0.17345(11) 0.75140(8) 0.0384(2) Uani 1 1 d . . . C15 C 0.18666(15) 0.28790(16) 0.35878(13) 0.0264(3) Uani 1 1 d . . . H15A H 0.1801 0.2655 0.4477 0.032 Uiso 1 1 calc R . . C16 C 0.12909(15) 0.44180(15) 0.28793(13) 0.0245(3) Uani 1 1 d . . . C17 C 0.20074(15) 0.54235(16) 0.17189(13) 0.0258(3) Uani 1 1 d . . . F17 F 0.33573(9) 0.50335(10) 0.11586(8) 0.0348(2) Uani 1 1 d . . . C18 C 0.14064(16) 0.68686(16) 0.11146(13) 0.0278(3) Uani 1 1 d . . . F18 F 0.21394(10) 0.77914(10) 0.00000(8) 0.0380(2) Uani 1 1 d . . . C19 C 0.00547(16) 0.73684(16) 0.16691(14) 0.0288(3) Uani 1 1 d . . . F19 F -0.05455(11) 0.87519(10) 0.10915(9) 0.0427(2) Uani 1 1 d . . . C20 C -0.06686(15) 0.64302(16) 0.28371(13) 0.0278(3) Uani 1 1 d . . . F20 F -0.19745(10) 0.69155(11) 0.33906(9) 0.0389(2) Uani 1 1 d . . . C21 C -0.00578(15) 0.49943(16) 0.34116(12) 0.0253(3) Uani 1 1 d . . . F21 F -0.08192(10) 0.41034(10) 0.45399(8) 0.0331(2) 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 0.0234(6) 0.0219(6) 0.0307(7) -0.0085(5) -0.0070(5) 0.0000(5) C2 0.0237(6) 0.0235(6) 0.0276(7) -0.0069(5) -0.0079(5) -0.0010(5) C3 0.0350(8) 0.0264(7) 0.0282(7) -0.0107(6) -0.0115(6) 0.0046(6) C4 0.0372(8) 0.0355(8) 0.0258(7) -0.0091(6) -0.0034(6) 0.0043(6) C5 0.0341(8) 0.0347(8) 0.0323(7) -0.0141(6) -0.0055(6) 0.0083(6) C6 0.0356(8) 0.0241(7) 0.0321(7) -0.0110(6) -0.0113(6) 0.0034(6) C7 0.0399(8) 0.0306(7) 0.0384(8) -0.0164(6) -0.0164(7) 0.0040(6) C8 0.0261(7) 0.0236(6) 0.0294(7) -0.0091(6) -0.0058(5) 0.0022(5) C9 0.0265(7) 0.0241(6) 0.0266(6) -0.0080(5) -0.0084(5) -0.0009(5) C10 0.0253(7) 0.0248(7) 0.0274(7) -0.0073(5) -0.0074(5) -0.0015(5) F10 0.0262(4) 0.0341(5) 0.0331(4) -0.0081(4) -0.0010(3) 0.0021(3) C11 0.0321(7) 0.0259(7) 0.0368(8) -0.0128(6) -0.0149(6) 0.0040(6) F11 0.0416(5) 0.0313(5) 0.0508(6) -0.0154(4) -0.0177(4) 0.0137(4) C12 0.0452(9) 0.0222(7) 0.0320(7) -0.0035(6) -0.0191(6) -0.0026(6) F12 0.0712(7) 0.0255(5) 0.0405(5) 0.0016(4) -0.0231(5) 0.0007(4) C13 0.0365(8) 0.0328(8) 0.0229(6) -0.0057(6) -0.0068(6) -0.0102(6) F13 0.0518(6) 0.0459(6) 0.0252(4) -0.0040(4) -0.0011(4) -0.0164(4) C14 0.0259(7) 0.0311(7) 0.0284(7) -0.0110(6) -0.0064(5) -0.0011(5) F14 0.0314(5) 0.0440(5) 0.0346(5) -0.0120(4) -0.0004(4) 0.0054(4) C15 0.0301(7) 0.0242(7) 0.0239(6) -0.0059(5) -0.0077(5) 0.0010(5) C16 0.0284(7) 0.0224(6) 0.0259(6) -0.0106(5) -0.0090(5) 0.0012(5) C17 0.0249(6) 0.0248(7) 0.0296(7) -0.0120(6) -0.0051(5) 0.0009(5) F17 0.0271(4) 0.0327(5) 0.0393(5) -0.0105(4) 0.0019(3) 0.0018(3) C18 0.0325(7) 0.0232(6) 0.0265(7) -0.0063(5) -0.0047(5) -0.0044(5) F18 0.0443(5) 0.0280(4) 0.0327(5) -0.0022(4) 0.0005(4) -0.0047(4) C19 0.0338(7) 0.0207(6) 0.0338(7) -0.0092(6) -0.0118(6) 0.0028(5) F19 0.0474(6) 0.0258(5) 0.0481(6) -0.0053(4) -0.0124(4) 0.0109(4) C20 0.0255(7) 0.0293(7) 0.0327(7) -0.0168(6) -0.0051(5) 0.0024(5) F20 0.0322(5) 0.0402(5) 0.0440(5) -0.0197(4) -0.0013(4) 0.0090(4) C21 0.0295(7) 0.0257(7) 0.0227(6) -0.0097(5) -0.0048(5) -0.0036(5) F21 0.0371(5) 0.0332(5) 0.0260(4) -0.0084(3) -0.0002(3) -0.0041(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 C1 C8 1.3359(19) . ? C1 C2 1.4915(18) . ? C1 C6 1.5145(19) . ? C2 C15 1.3341(19) . ? C2 C3 1.5086(19) . ? C3 C7 1.536(2) . ? C3 C4 1.547(2) . ? C3 H3A 1.0000 . ? C4 C5 1.550(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.544(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5435(19) . ? C6 H6A 1.0000 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.4668(18) . ? C8 H8A 0.9500 . ? C9 C10 1.3893(19) . ? C9 C14 1.395(2) . ? C10 F10 1.3348(16) . ? C10 C11 1.381(2) . ? C11 F11 1.3385(16) . ? C11 C12 1.376(2) . ? C12 F12 1.3348(16) . ? C12 C13 1.375(2) . ? C13 F13 1.3378(17) . ? C13 C14 1.378(2) . ? C14 F14 1.3388(16) . ? C15 C16 1.4691(18) . ? C15 H15A 0.9500 . ? C16 C17 1.391(2) . ? C16 C21 1.3938(18) . ? C17 F17 1.3395(16) . ? C17 C18 1.3824(19) . ? C18 F18 1.3360(16) . ? C18 C19 1.376(2) . ? C19 F19 1.3325(16) . ? C19 C20 1.377(2) . ? C20 F20 1.3382(15) . ? C20 C21 1.3717(19) . ? C21 F21 1.3455(16) . ? 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 C1 C2 125.16(12) . . ? C8 C1 C6 129.90(13) . . ? C2 C1 C6 104.81(11) . . ? C15 C2 C1 125.31(12) . . ? C15 C2 C3 129.57(12) . . ? C1 C2 C3 104.97(11) . . ? C2 C3 C7 100.45(11) . . ? C2 C3 C4 107.24(11) . . ? C7 C3 C4 100.98(12) . . ? C2 C3 H3A 115.4 . . ? C7 C3 H3A 115.4 . . ? C4 C3 H3A 115.4 . . ? C3 C4 C5 103.56(12) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C4 103.33(11) . . ? C6 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? C6 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? C1 C6 C7 100.29(11) . . ? C1 C6 C5 107.49(11) . . ? C7 C6 C5 100.79(12) . . ? C1 C6 H6A 115.4 . . ? C7 C6 H6A 115.4 . . ? C5 C6 H6A 115.4 . . ? C3 C7 C6 94.88(11) . . ? C3 C7 H7A 112.8 . . ? C6 C7 H7A 112.8 . . ? C3 C7 H7B 112.8 . . ? C6 C7 H7B 112.8 . . ? H7A C7 H7B 110.2 . . ? C1 C8 C9 127.71(13) . . ? C1 C8 H8A 116.1 . . ? C9 C8 H8A 116.1 . . ? C10 C9 C14 115.36(13) . . ? C10 C9 C8 125.47(13) . . ? C14 C9 C8 119.16(12) . . ? F10 C10 C11 116.99(12) . . ? F10 C10 C9 120.36(12) . . ? C11 C10 C9 122.64(13) . . ? F11 C11 C12 120.14(13) . . ? F11 C11 C10 120.01(14) . . ? C12 C11 C10 119.86(13) . . ? F12 C12 C13 120.23(14) . . ? F12 C12 C11 120.16(14) . . ? C13 C12 C11 119.60(13) . . ? F13 C13 C12 119.86(13) . . ? F13 C13 C14 120.58(14) . . ? C12 C13 C14 119.53(13) . . ? F14 C14 C13 117.66(13) . . ? F14 C14 C9 119.35(12) . . ? C13 C14 C9 122.96(13) . . ? C2 C15 C16 127.36(12) . . ? C2 C15 H15A 116.3 . . ? C16 C15 H15A 116.3 . . ? C17 C16 C21 115.06(12) . . ? C17 C16 C15 125.83(12) . . ? C21 C16 C15 119.04(12) . . ? F17 C17 C18 117.03(12) . . ? F17 C17 C16 120.28(12) . . ? C18 C17 C16 122.65(12) . . ? F18 C18 C19 119.73(12) . . ? F18 C18 C17 120.34(13) . . ? C19 C18 C17 119.92(13) . . ? F19 C19 C18 120.58(13) . . ? F19 C19 C20 120.11(13) . . ? C18 C19 C20 119.30(13) . . ? F20 C20 C21 120.61(13) . . ? F20 C20 C19 119.70(12) . . ? C21 C20 C19 119.68(12) . . ? F21 C21 C20 117.64(12) . . ? F21 C21 C16 119.02(12) . . ? C20 C21 C16 123.33(13) . . ? 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 C1 C2 C15 -0.8(2) . . . . ? C6 C1 C2 C15 175.43(13) . . . . ? C8 C1 C2 C3 -176.59(13) . . . . ? C6 C1 C2 C3 -0.40(14) . . . . ? C15 C2 C3 C7 -140.59(15) . . . . ? C1 C2 C3 C7 34.99(13) . . . . ? C15 C2 C3 C4 114.34(16) . . . . ? C1 C2 C3 C4 -70.08(13) . . . . ? C2 C3 C4 C5 69.99(14) . . . . ? C7 C3 C4 C5 -34.71(13) . . . . ? C3 C4 C5 C6 -0.71(14) . . . . ? C8 C1 C6 C7 141.82(15) . . . . ? C2 C1 C6 C7 -34.13(14) . . . . ? C8 C1 C6 C5 -113.30(16) . . . . ? C2 C1 C6 C5 70.75(13) . . . . ? C4 C5 C6 C1 -68.84(14) . . . . ? C4 C5 C6 C7 35.68(13) . . . . ? C2 C3 C7 C6 -54.33(12) . . . . ? C4 C3 C7 C6 55.72(12) . . . . ? C1 C6 C7 C3 53.97(13) . . . . ? C5 C6 C7 C3 -56.24(13) . . . . ? C2 C1 C8 C9 175.75(13) . . . . ? C6 C1 C8 C9 0.5(2) . . . . ? C1 C8 C9 C10 41.2(2) . . . . ? C1 C8 C9 C14 -140.23(15) . . . . ? C14 C9 C10 F10 -176.28(11) . . . . ? C8 C9 C10 F10 2.4(2) . . . . ? C14 C9 C10 C11 2.43(19) . . . . ? C8 C9 C10 C11 -178.90(13) . . . . ? F10 C10 C11 F11 -1.91(19) . . . . ? C9 C10 C11 F11 179.35(12) . . . . ? F10 C10 C11 C12 178.03(12) . . . . ? C9 C10 C11 C12 -0.7(2) . . . . ? F11 C11 C12 F12 -1.8(2) . . . . ? C10 C11 C12 F12 178.26(12) . . . . ? F11 C11 C12 C13 178.88(12) . . . . ? C10 C11 C12 C13 -1.1(2) . . . . ? F12 C12 C13 F13 -0.5(2) . . . . ? C11 C12 C13 F13 178.78(12) . . . . ? F12 C12 C13 C14 -178.37(12) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? F13 C13 C14 F14 1.3(2) . . . . ? C12 C13 C14 F14 179.11(12) . . . . ? F13 C13 C14 C9 -176.88(12) . . . . ? C12 C13 C14 C9 0.9(2) . . . . ? C10 C9 C14 F14 179.31(11) . . . . ? C8 C9 C14 F14 0.55(19) . . . . ? C10 C9 C14 C13 -2.5(2) . . . . ? C8 C9 C14 C13 178.69(12) . . . . ? C1 C2 C15 C16 -174.87(13) . . . . ? C3 C2 C15 C16 -0.1(2) . . . . ? C2 C15 C16 C17 -45.9(2) . . . . ? C2 C15 C16 C21 137.17(15) . . . . ? C21 C16 C17 F17 175.75(11) . . . . ? C15 C16 C17 F17 -1.3(2) . . . . ? C21 C16 C17 C18 -2.01(19) . . . . ? C15 C16 C17 C18 -179.02(12) . . . . ? F17 C17 C18 F18 2.19(19) . . . . ? C16 C17 C18 F18 -179.98(12) . . . . ? F17 C17 C18 C19 -177.08(12) . . . . ? C16 C17 C18 C19 0.7(2) . . . . ? F18 C18 C19 F19 1.4(2) . . . . ? C17 C18 C19 F19 -179.32(12) . . . . ? F18 C18 C19 C20 -177.92(12) . . . . ? C17 C18 C19 C20 1.4(2) . . . . ? F19 C19 C20 F20 -0.2(2) . . . . ? C18 C19 C20 F20 179.17(12) . . . . ? F19 C19 C20 C21 178.62(12) . . . . ? C18 C19 C20 C21 -2.0(2) . . . . ? F20 C20 C21 F21 0.15(19) . . . . ? C19 C20 C21 F21 -178.62(12) . . . . ? F20 C20 C21 C16 179.46(12) . . . . ? C19 C20 C21 C16 0.7(2) . . . . ? C17 C16 C21 F21 -179.40(11) . . . . ? C15 C16 C21 F21 -2.17(18) . . . . ? C17 C16 C21 C20 1.30(19) . . . . ? C15 C16 C21 C20 178.53(12) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.364 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.047 data_02304aaa _database_code_CSD 203758 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 02304aaa _chemical_melting_point ? _chemical_formula_moiety '(C21 H10 F10) (C21 H20)' _chemical_formula_sum 'C42 H30 F10' _chemical_formula_weight 724.66 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' F F 0.0171 0.0103 '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 10.550(3) _cell_length_b 12.981(3) _cell_length_c 13.366(3) _cell_angle_alpha 103.043(5) _cell_angle_beta 90.336(5) _cell_angle_gamma 113.064(5) _cell_volume 1631.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3239 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 24.62 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9518 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2002)' _exptl_special_details 'Prof. J. Liu - Murray State University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-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 20077 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5744 _reflns_number_gt 3884 _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^)+(0.0390P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5744 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7343(2) 0.58892(19) 0.39388(16) 0.0298(5) Uani 1 1 d . . . C2 C 0.6126(2) 0.48530(19) 0.33646(16) 0.0297(5) Uani 1 1 d . . . C3 C 0.5181(3) 0.53252(19) 0.29592(17) 0.0341(6) Uani 1 1 d . . . H3A H 0.4491 0.4782 0.2362 0.041 Uiso 1 1 calc R . . C4 C 0.4563(3) 0.5843(2) 0.38825(17) 0.0375(6) Uani 1 1 d . . . H4A H 0.4179 0.5295 0.4322 0.045 Uiso 1 1 calc R . . H4B H 0.3826 0.6052 0.3647 0.045 Uiso 1 1 calc R . . C5 C 0.5833(3) 0.6935(2) 0.44706(18) 0.0390(6) Uani 1 1 d . . . H5A H 0.5681 0.7646 0.4500 0.047 Uiso 1 1 calc R . . H5B H 0.6024 0.6892 0.5183 0.047 Uiso 1 1 calc R . . C6 C 0.7028(3) 0.6909(2) 0.38228(17) 0.0340(6) Uani 1 1 d . . . H6A H 0.7852 0.7662 0.3934 0.041 Uiso 1 1 calc R . . C7 C 0.6259(3) 0.64281(19) 0.27242(17) 0.0378(6) Uani 1 1 d . . . H7A H 0.5839 0.6930 0.2538 0.045 Uiso 1 1 calc R . . H7B H 0.6847 0.6263 0.2190 0.045 Uiso 1 1 calc R . . C8 C 0.8479(3) 0.58908(19) 0.43910(16) 0.0325(6) Uani 1 1 d . . . H8A H 0.8475 0.5150 0.4353 0.039 Uiso 1 1 calc R . . C9 C 0.9733(3) 0.68790(19) 0.49393(17) 0.0309(6) Uani 1 1 d . . . C10 C 0.9707(3) 0.7914(2) 0.55229(17) 0.0378(6) Uani 1 1 d . . . H10A H 0.8850 0.7991 0.5578 0.045 Uiso 1 1 calc R . . C11 C 1.0913(3) 0.8821(2) 0.60185(19) 0.0449(7) Uani 1 1 d . . . H11A H 1.0874 0.9513 0.6413 0.054 Uiso 1 1 calc R . . C12 C 1.2170(3) 0.8735(2) 0.59481(19) 0.0444(7) Uani 1 1 d . . . H12A H 1.2997 0.9367 0.6281 0.053 Uiso 1 1 calc R . . C13 C 1.2214(3) 0.7716(2) 0.53857(18) 0.0399(6) Uani 1 1 d . . . H13A H 1.3076 0.7646 0.5338 0.048 Uiso 1 1 calc R . . C14 C 1.1011(3) 0.6800(2) 0.48929(17) 0.0345(6) Uani 1 1 d . . . H14A H 1.1057 0.6103 0.4516 0.041 Uiso 1 1 calc R . . C15 C 0.5979(2) 0.37503(19) 0.32060(16) 0.0333(6) Uani 1 1 d . . . H15A H 0.6726 0.3637 0.3493 0.040 Uiso 1 1 calc R . . C16 C 0.4806(2) 0.26948(19) 0.26431(17) 0.0320(6) Uani 1 1 d . . . C17 C 0.3439(3) 0.2585(2) 0.26340(18) 0.0380(6) Uani 1 1 d . . . H17A H 0.3238 0.3213 0.2997 0.046 Uiso 1 1 calc R . . C18 C 0.2371(3) 0.1571(2) 0.21016(19) 0.0433(7) Uani 1 1 d . . . H18A H 0.1442 0.1507 0.2109 0.052 Uiso 1 1 calc R . . C19 C 0.2640(3) 0.0650(2) 0.15596(19) 0.0438(7) Uani 1 1 d . . . H19A H 0.1905 -0.0038 0.1184 0.053 Uiso 1 1 calc R . . C20 C 0.3989(3) 0.0740(2) 0.15692(19) 0.0438(7) Uani 1 1 d . . . H20A H 0.4182 0.0110 0.1200 0.053 Uiso 1 1 calc R . . C21 C 0.5059(3) 0.17422(19) 0.21134(18) 0.0376(6) Uani 1 1 d . . . H21A H 0.5980 0.1787 0.2129 0.045 Uiso 1 1 calc R . . C22 C 0.1340(2) 0.40343(18) 0.10724(16) 0.0269(5) Uani 1 1 d . . . C23 C 0.1186(2) 0.51112(18) 0.16148(16) 0.0280(5) Uani 1 1 d . . . C24 C -0.0126(2) 0.46965(19) 0.21353(17) 0.0325(6) Uani 1 1 d . . . H24A H -0.0229 0.5290 0.2713 0.039 Uiso 1 1 calc R . . C25 C -0.1361(2) 0.40705(19) 0.12784(17) 0.0353(6) Uani 1 1 d . . . H25A H -0.1302 0.4541 0.0778 0.042 Uiso 1 1 calc R . . H25B H -0.2255 0.3903 0.1577 0.042 Uiso 1 1 calc R . . C26 C -0.1203(2) 0.29360(19) 0.07561(18) 0.0359(6) Uani 1 1 d . . . H26A H -0.2006 0.2249 0.0840 0.043 Uiso 1 1 calc R . . H26B H -0.1105 0.2873 0.0011 0.043 Uiso 1 1 calc R . . C27 C 0.0139(2) 0.30650(19) 0.13455(17) 0.0318(6) Uani 1 1 d . . . H27A H 0.0268 0.2330 0.1280 0.038 Uiso 1 1 calc R . . C28 C -0.0004(3) 0.36611(19) 0.24478(17) 0.0374(6) Uani 1 1 d . . . H28A H 0.0827 0.3893 0.2935 0.045 Uiso 1 1 calc R . . H28B H -0.0845 0.3193 0.2727 0.045 Uiso 1 1 calc R . . C29 C 0.2383(2) 0.39882(18) 0.05223(16) 0.0288(5) Uani 1 1 d . . . H29A H 0.3040 0.4708 0.0442 0.035 Uiso 1 1 calc R . . C30 C 0.2640(2) 0.29636(18) 0.00259(16) 0.0274(5) Uani 1 1 d . . . C31 C 0.1633(2) 0.18884(19) -0.04917(17) 0.0302(6) Uani 1 1 d . . . F31 F 0.02956(13) 0.17313(10) -0.05928(10) 0.0389(3) Uani 1 1 d . . . C32 C 0.1937(3) 0.09666(19) -0.09322(17) 0.0344(6) Uani 1 1 d . . . F32 F 0.09087(16) -0.00615(11) -0.13988(11) 0.0540(4) Uani 1 1 d . . . C33 C 0.3273(3) 0.1063(2) -0.08952(18) 0.0385(6) Uani 1 1 d . . . F33 F 0.35705(17) 0.01532(12) -0.13104(12) 0.0591(5) Uani 1 1 d . . . C34 C 0.4321(2) 0.2112(2) -0.04044(18) 0.0329(6) Uani 1 1 d . . . F34 F 0.56323(14) 0.22159(11) -0.03499(11) 0.0453(4) Uani 1 1 d . . . C35 C 0.3991(2) 0.30259(19) 0.00334(17) 0.0295(5) Uani 1 1 d . . . F35 F 0.50452(14) 0.40348(10) 0.05067(10) 0.0390(3) Uani 1 1 d . . . C36 C 0.2092(2) 0.61965(18) 0.16888(17) 0.0309(6) Uani 1 1 d . . . H36A H 0.2879 0.6286 0.1319 0.037 Uiso 1 1 calc R . . C37 C 0.2008(2) 0.72678(18) 0.22786(17) 0.0302(6) Uani 1 1 d . . . F38 F -0.03789(14) 0.66899(10) 0.17641(10) 0.0407(4) Uani 1 1 d . . . C38 C 0.0810(3) 0.74730(18) 0.23336(17) 0.0311(6) Uani 1 1 d . . . F39 F -0.04026(15) 0.86502(11) 0.29076(11) 0.0467(4) Uani 1 1 d . . . C39 C 0.0777(3) 0.8482(2) 0.29158(18) 0.0340(6) Uani 1 1 d . . . F40 F 0.19261(17) 1.03086(11) 0.40706(10) 0.0505(4) Uani 1 1 d . . . C40 C 0.1959(3) 0.93297(19) 0.34914(18) 0.0354(6) Uani 1 1 d . . . F41 F 0.43399(17) 1.00161(11) 0.39896(11) 0.0545(4) Uani 1 1 d . . . C41 C 0.3174(3) 0.91818(19) 0.34433(18) 0.0355(6) Uani 1 1 d . . . C42 C 0.3190(2) 0.81772(19) 0.28404(18) 0.0325(6) Uani 1 1 d . . . F42 F 0.44069(15) 0.80713(11) 0.28121(11) 0.0472(4) 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 0.0308(14) 0.0359(13) 0.0257(12) 0.0087(10) 0.0087(11) 0.0159(12) C2 0.0300(14) 0.0400(14) 0.0220(12) 0.0084(10) 0.0054(11) 0.0166(12) C3 0.0341(14) 0.0423(14) 0.0273(13) 0.0070(11) 0.0009(11) 0.0175(13) C4 0.0360(15) 0.0475(15) 0.0362(14) 0.0121(12) 0.0076(12) 0.0233(14) C5 0.0398(16) 0.0446(14) 0.0364(14) 0.0078(11) 0.0040(13) 0.0220(14) C6 0.0334(14) 0.0369(13) 0.0351(14) 0.0119(11) 0.0052(12) 0.0161(12) C7 0.0411(16) 0.0497(15) 0.0335(14) 0.0159(11) 0.0076(12) 0.0265(14) C8 0.0360(15) 0.0338(13) 0.0291(13) 0.0076(10) 0.0042(12) 0.0157(12) C9 0.0352(15) 0.0343(13) 0.0260(12) 0.0108(10) 0.0018(11) 0.0150(12) C10 0.0363(15) 0.0444(15) 0.0364(14) 0.0061(12) 0.0054(12) 0.0223(14) C11 0.0463(18) 0.0376(14) 0.0430(15) -0.0009(12) -0.0016(14) 0.0147(14) C12 0.0413(17) 0.0406(15) 0.0408(15) 0.0070(12) -0.0058(14) 0.0075(14) C13 0.0308(15) 0.0540(16) 0.0386(15) 0.0152(13) 0.0013(13) 0.0190(14) C14 0.0373(16) 0.0399(14) 0.0292(13) 0.0082(11) 0.0022(12) 0.0188(13) C15 0.0295(14) 0.0426(14) 0.0304(13) 0.0111(11) 0.0023(11) 0.0160(13) C16 0.0311(14) 0.0377(13) 0.0296(13) 0.0125(11) 0.0023(12) 0.0140(13) C17 0.0350(16) 0.0424(15) 0.0375(14) 0.0122(12) 0.0012(13) 0.0151(14) C18 0.0293(15) 0.0564(17) 0.0470(16) 0.0258(14) -0.0004(13) 0.0131(14) C19 0.0392(17) 0.0406(15) 0.0416(15) 0.0152(12) -0.0055(14) 0.0033(14) C20 0.0458(18) 0.0329(14) 0.0477(16) 0.0101(12) 0.0038(15) 0.0105(14) C21 0.0316(15) 0.0373(14) 0.0447(15) 0.0118(12) 0.0034(13) 0.0139(13) C22 0.0265(13) 0.0283(12) 0.0263(12) 0.0080(10) -0.0012(11) 0.0109(11) C23 0.0306(14) 0.0326(13) 0.0223(12) 0.0072(10) 0.0016(11) 0.0141(12) C24 0.0365(15) 0.0358(13) 0.0287(13) 0.0090(10) 0.0082(12) 0.0176(12) C25 0.0260(13) 0.0402(14) 0.0401(14) 0.0110(11) 0.0074(12) 0.0132(12) C26 0.0279(14) 0.0340(13) 0.0419(15) 0.0071(11) 0.0047(12) 0.0098(12) C27 0.0314(14) 0.0285(12) 0.0363(14) 0.0110(10) 0.0077(12) 0.0113(12) C28 0.0405(16) 0.0401(14) 0.0357(14) 0.0173(11) 0.0120(12) 0.0160(13) C29 0.0276(13) 0.0250(12) 0.0309(13) 0.0052(10) 0.0019(11) 0.0087(11) C30 0.0292(14) 0.0274(12) 0.0249(12) 0.0071(10) 0.0032(11) 0.0103(11) C31 0.0259(14) 0.0330(13) 0.0313(13) 0.0069(11) 0.0010(11) 0.0122(12) F31 0.0267(8) 0.0361(7) 0.0470(8) 0.0001(6) -0.0053(7) 0.0111(7) C32 0.0337(15) 0.0258(13) 0.0359(14) 0.0012(10) -0.0041(12) 0.0074(12) F32 0.0462(10) 0.0309(8) 0.0673(10) -0.0083(7) -0.0095(8) 0.0085(8) C33 0.0449(17) 0.0331(14) 0.0401(15) 0.0003(11) 0.0033(13) 0.0232(14) F33 0.0583(11) 0.0420(9) 0.0765(11) -0.0042(8) 0.0051(9) 0.0299(9) C34 0.0266(14) 0.0429(15) 0.0347(14) 0.0107(11) 0.0074(12) 0.0191(13) F34 0.0321(8) 0.0518(9) 0.0549(9) 0.0098(7) 0.0092(7) 0.0216(8) C35 0.0273(14) 0.0279(12) 0.0272(12) 0.0048(10) 0.0043(11) 0.0057(12) F35 0.0267(8) 0.0341(7) 0.0456(8) 0.0040(6) 0.0049(7) 0.0043(7) C36 0.0300(14) 0.0333(13) 0.0325(13) 0.0084(10) 0.0064(11) 0.0157(12) C37 0.0321(14) 0.0293(13) 0.0294(13) 0.0089(10) 0.0020(12) 0.0116(12) F38 0.0311(8) 0.0354(7) 0.0532(9) 0.0082(6) -0.0019(7) 0.0126(7) C38 0.0303(14) 0.0278(13) 0.0338(13) 0.0094(11) 0.0010(12) 0.0094(12) F39 0.0420(9) 0.0441(8) 0.0625(10) 0.0141(7) 0.0143(8) 0.0257(8) C39 0.0353(15) 0.0375(14) 0.0372(14) 0.0150(12) 0.0121(13) 0.0199(13) F40 0.0692(11) 0.0344(8) 0.0486(9) 0.0024(6) 0.0062(8) 0.0259(8) C40 0.0506(18) 0.0257(13) 0.0333(14) 0.0079(11) 0.0072(13) 0.0186(13) F41 0.0524(10) 0.0360(8) 0.0609(10) 0.0001(7) -0.0165(9) 0.0100(8) C41 0.0368(16) 0.0281(13) 0.0354(14) 0.0056(11) -0.0059(13) 0.0080(13) C42 0.0295(14) 0.0335(14) 0.0378(14) 0.0111(11) 0.0031(12) 0.0151(13) F42 0.0329(8) 0.0403(8) 0.0657(10) 0.0070(7) -0.0045(8) 0.0154(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C8 1.338(3) . ? C1 C2 1.489(3) . ? C1 C6 1.524(3) . ? C2 C15 1.344(3) . ? C2 C3 1.512(3) . ? C3 C7 1.541(3) . ? C3 C4 1.542(3) . ? C3 H3A 1.0000 . ? C4 C5 1.556(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.541(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.543(3) . ? C6 H6A 1.0000 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.473(3) . ? C8 H8A 0.9500 . ? C9 C14 1.392(3) . ? C9 C10 1.403(3) . ? C10 C11 1.382(3) . ? C10 H10A 0.9500 . ? C11 C12 1.375(4) . ? C11 H11A 0.9500 . ? C12 C13 1.384(3) . ? C12 H12A 0.9500 . ? C13 C14 1.383(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.473(3) . ? C15 H15A 0.9500 . ? C16 C17 1.392(3) . ? C16 C21 1.403(3) . ? C17 C18 1.384(3) . ? C17 H17A 0.9500 . ? C18 C19 1.383(4) . ? C18 H18A 0.9500 . ? C19 C20 1.381(4) . ? C19 H19A 0.9500 . ? C20 C21 1.381(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C29 1.340(3) . ? C22 C23 1.493(3) . ? C22 C27 1.512(3) . ? C23 C36 1.338(3) . ? C23 C24 1.512(3) . ? C24 C28 1.545(3) . ? C24 C25 1.550(3) . ? C24 H24A 1.0000 . ? C25 C26 1.554(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.548(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.540(3) . ? C27 H27A 1.0000 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.472(3) . ? C29 H29A 0.9500 . ? C30 C35 1.395(3) . ? C30 C31 1.396(3) . ? C31 F31 1.345(3) . ? C31 C32 1.366(3) . ? C32 F32 1.352(3) . ? C32 C33 1.365(4) . ? C33 F33 1.341(3) . ? C33 C34 1.384(3) . ? C34 F34 1.336(3) . ? C34 C35 1.373(3) . ? C35 F35 1.352(2) . ? C36 C37 1.472(3) . ? C36 H36A 0.9500 . ? C37 C38 1.389(3) . ? C37 C42 1.396(3) . ? F38 C38 1.351(3) . ? C38 C39 1.377(3) . ? F39 C39 1.345(3) . ? C39 C40 1.375(3) . ? F40 C40 1.344(3) . ? C40 C41 1.368(4) . ? F41 C41 1.345(3) . ? C41 C42 1.376(3) . ? C42 F42 1.344(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C1 C2 126.3(2) . . ? C8 C1 C6 129.2(2) . . ? C2 C1 C6 104.42(19) . . ? C15 C2 C1 125.8(2) . . ? C15 C2 C3 128.9(2) . . ? C1 C2 C3 105.13(18) . . ? C2 C3 C7 100.37(19) . . ? C2 C3 C4 108.20(18) . . ? C7 C3 C4 101.21(18) . . ? C2 C3 H3A 115.1 . . ? C7 C3 H3A 115.1 . . ? C4 C3 H3A 115.1 . . ? C3 C4 C5 102.97(19) . . ? C3 C4 H4A 111.2 . . ? C5 C4 H4A 111.2 . . ? C3 C4 H4B 111.2 . . ? C5 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? C6 C5 C4 103.56(19) . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5B 111.0 . . ? C4 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C1 C6 C5 108.13(18) . . ? C1 C6 C7 100.39(18) . . ? C5 C6 C7 100.7(2) . . ? C1 C6 H6A 115.2 . . ? C5 C6 H6A 115.2 . . ? C7 C6 H6A 115.2 . . ? C3 C7 C6 94.43(17) . . ? C3 C7 H7A 112.8 . . ? C6 C7 H7A 112.8 . . ? C3 C7 H7B 112.8 . . ? C6 C7 H7B 112.8 . . ? H7A C7 H7B 110.3 . . ? C1 C8 C9 129.1(2) . . ? C1 C8 H8A 115.4 . . ? C9 C8 H8A 115.4 . . ? C14 C9 C10 117.6(2) . . ? C14 C9 C8 119.6(2) . . ? C10 C9 C8 122.9(2) . . ? C11 C10 C9 120.8(2) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C9 121.2(2) . . ? C13 C14 H14A 119.4 . . ? C9 C14 H14A 119.4 . . ? C2 C15 C16 128.2(2) . . ? C2 C15 H15A 115.9 . . ? C16 C15 H15A 115.9 . . ? C17 C16 C21 118.0(2) . . ? C17 C16 C15 122.8(2) . . ? C21 C16 C15 119.2(2) . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C20 C19 C18 119.4(2) . . ? C20 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C19 C20 C21 120.3(3) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C16 120.9(2) . . ? C20 C21 H21A 119.5 . . ? C16 C21 H21A 119.5 . . ? C29 C22 C23 125.6(2) . . ? C29 C22 C27 129.4(2) . . ? C23 C22 C27 104.83(19) . . ? C36 C23 C22 126.4(2) . . ? C36 C23 C24 128.5(2) . . ? C22 C23 C24 104.79(18) . . ? C23 C24 C28 99.84(19) . . ? C23 C24 C25 107.71(18) . . ? C28 C24 C25 101.23(18) . . ? C23 C24 H24A 115.4 . . ? C28 C24 H24A 115.4 . . ? C25 C24 H24A 115.4 . . ? C24 C25 C26 103.63(19) . . ? C24 C25 H25A 111.0 . . ? C26 C25 H25A 111.0 . . ? C24 C25 H25B 111.0 . . ? C26 C25 H25B 111.0 . . ? H25A C25 H25B 109.0 . . ? C27 C26 C25 102.95(18) . . ? C27 C26 H26A 111.2 . . ? C25 C26 H26A 111.2 . . ? C27 C26 H26B 111.2 . . ? C25 C26 H26B 111.2 . . ? H26A C26 H26B 109.1 . . ? C22 C27 C28 100.66(18) . . ? C22 C27 C26 108.01(18) . . ? C28 C27 C26 100.9(2) . . ? C22 C27 H27A 115.1 . . ? C28 C27 H27A 115.1 . . ? C26 C27 H27A 115.1 . . ? C27 C28 C24 94.56(17) . . ? C27 C28 H28A 112.8 . . ? C24 C28 H28A 112.8 . . ? C27 C28 H28B 112.8 . . ? C24 C28 H28B 112.8 . . ? H28A C28 H28B 110.3 . . ? C22 C29 C30 128.2(2) . . ? C22 C29 H29A 115.9 . . ? C30 C29 H29A 115.9 . . ? C35 C30 C31 114.2(2) . . ? C35 C30 C29 120.0(2) . . ? C31 C30 C29 125.8(2) . . ? F31 C31 C32 117.0(2) . . ? F31 C31 C30 120.0(2) . . ? C32 C31 C30 123.0(2) . . ? F32 C32 C33 119.2(2) . . ? F32 C32 C31 120.1(2) . . ? C33 C32 C31 120.7(2) . . ? F33 C33 C32 120.8(2) . . ? F33 C33 C34 120.2(2) . . ? C32 C33 C34 119.0(2) . . ? F34 C34 C35 121.1(2) . . ? F34 C34 C33 119.7(2) . . ? C35 C34 C33 119.2(2) . . ? F35 C35 C34 117.3(2) . . ? F35 C35 C30 118.9(2) . . ? C34 C35 C30 123.8(2) . . ? C23 C36 C37 127.3(2) . . ? C23 C36 H36A 116.3 . . ? C37 C36 H36A 116.3 . . ? C38 C37 C42 114.7(2) . . ? C38 C37 C36 125.1(2) . . ? C42 C37 C36 120.2(2) . . ? F38 C38 C39 116.9(2) . . ? F38 C38 C37 120.2(2) . . ? C39 C38 C37 122.9(2) . . ? F39 C39 C40 119.8(2) . . ? F39 C39 C38 120.2(2) . . ? C40 C39 C38 120.0(2) . . ? F40 C40 C41 120.5(2) . . ? F40 C40 C39 120.1(2) . . ? C41 C40 C39 119.4(2) . . ? F41 C41 C40 119.8(2) . . ? F41 C41 C42 120.6(2) . . ? C40 C41 C42 119.7(2) . . ? F42 C42 C41 117.7(2) . . ? F42 C42 C37 119.1(2) . . ? C41 C42 C37 123.2(2) . . ? 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 C1 C2 C15 -0.3(4) . . . . ? C6 C1 C2 C15 176.1(2) . . . . ? C8 C1 C2 C3 -176.7(2) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? C15 C2 C3 C7 -141.0(2) . . . . ? C1 C2 C3 C7 35.3(2) . . . . ? C15 C2 C3 C4 113.4(3) . . . . ? C1 C2 C3 C4 -70.3(2) . . . . ? C2 C3 C4 C5 69.8(2) . . . . ? C7 C3 C4 C5 -35.2(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C8 C1 C6 C5 -113.4(3) . . . . ? C2 C1 C6 C5 70.4(2) . . . . ? C8 C1 C6 C7 141.6(2) . . . . ? C2 C1 C6 C7 -34.6(2) . . . . ? C4 C5 C6 C1 -68.8(2) . . . . ? C4 C5 C6 C7 35.9(2) . . . . ? C2 C3 C7 C6 -54.7(2) . . . . ? C4 C3 C7 C6 56.4(2) . . . . ? C1 C6 C7 C3 54.4(2) . . . . ? C5 C6 C7 C3 -56.5(2) . . . . ? C2 C1 C8 C9 177.8(2) . . . . ? C6 C1 C8 C9 2.4(4) . . . . ? C1 C8 C9 C14 -147.0(3) . . . . ? C1 C8 C9 C10 33.4(4) . . . . ? C14 C9 C10 C11 0.9(3) . . . . ? C8 C9 C10 C11 -179.6(2) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C9 0.7(4) . . . . ? C10 C9 C14 C13 -1.4(3) . . . . ? C8 C9 C14 C13 179.1(2) . . . . ? C1 C2 C15 C16 -179.8(2) . . . . ? C3 C2 C15 C16 -4.2(4) . . . . ? C2 C15 C16 C17 -33.8(4) . . . . ? C2 C15 C16 C21 148.0(2) . . . . ? C21 C16 C17 C18 -1.1(3) . . . . ? C15 C16 C17 C18 -179.4(2) . . . . ? C16 C17 C18 C19 -0.6(4) . . . . ? C17 C18 C19 C20 1.3(4) . . . . ? C18 C19 C20 C21 -0.2(4) . . . . ? C19 C20 C21 C16 -1.6(4) . . . . ? C17 C16 C21 C20 2.2(3) . . . . ? C15 C16 C21 C20 -179.5(2) . . . . ? C29 C22 C23 C36 -4.0(4) . . . . ? C27 C22 C23 C36 172.5(2) . . . . ? C29 C22 C23 C24 -178.6(2) . . . . ? C27 C22 C23 C24 -2.1(2) . . . . ? C36 C23 C24 C28 -137.9(2) . . . . ? C22 C23 C24 C28 36.5(2) . . . . ? C36 C23 C24 C25 116.8(2) . . . . ? C22 C23 C24 C25 -68.7(2) . . . . ? C23 C24 C25 C26 70.8(2) . . . . ? C28 C24 C25 C26 -33.5(2) . . . . ? C24 C25 C26 C27 -2.2(2) . . . . ? C29 C22 C27 C28 143.0(2) . . . . ? C23 C22 C27 C28 -33.3(2) . . . . ? C29 C22 C27 C26 -111.6(3) . . . . ? C23 C22 C27 C26 72.0(2) . . . . ? C25 C26 C27 C22 -67.9(2) . . . . ? C25 C26 C27 C28 37.2(2) . . . . ? C22 C27 C28 C24 54.0(2) . . . . ? C26 C27 C28 C24 -56.9(2) . . . . ? C23 C24 C28 C27 -55.2(2) . . . . ? C25 C24 C28 C27 55.3(2) . . . . ? C23 C22 C29 C30 175.8(2) . . . . ? C27 C22 C29 C30 0.2(4) . . . . ? C22 C29 C30 C35 -141.5(2) . . . . ? C22 C29 C30 C31 39.7(4) . . . . ? C35 C30 C31 F31 -177.10(19) . . . . ? C29 C30 C31 F31 1.8(3) . . . . ? C35 C30 C31 C32 1.5(3) . . . . ? C29 C30 C31 C32 -179.6(2) . . . . ? F31 C31 C32 F32 -3.1(3) . . . . ? C30 C31 C32 F32 178.21(19) . . . . ? F31 C31 C32 C33 177.8(2) . . . . ? C30 C31 C32 C33 -0.8(4) . . . . ? F32 C32 C33 F33 -0.3(4) . . . . ? C31 C32 C33 F33 178.7(2) . . . . ? F32 C32 C33 C34 -179.1(2) . . . . ? C31 C32 C33 C34 -0.1(4) . . . . ? F33 C33 C34 F34 0.3(3) . . . . ? C32 C33 C34 F34 179.1(2) . . . . ? F33 C33 C34 C35 -178.7(2) . . . . ? C32 C33 C34 C35 0.1(4) . . . . ? F34 C34 C35 F35 0.9(3) . . . . ? C33 C34 C35 F35 179.91(19) . . . . ? F34 C34 C35 C30 -178.3(2) . . . . ? C33 C34 C35 C30 0.7(4) . . . . ? C31 C30 C35 F35 179.35(17) . . . . ? C29 C30 C35 F35 0.4(3) . . . . ? C31 C30 C35 C34 -1.4(3) . . . . ? C29 C30 C35 C34 179.6(2) . . . . ? C22 C23 C36 C37 -175.4(2) . . . . ? C24 C23 C36 C37 -2.1(4) . . . . ? C23 C36 C37 C38 -41.6(3) . . . . ? C23 C36 C37 C42 138.4(2) . . . . ? C42 C37 C38 F38 175.31(18) . . . . ? C36 C37 C38 F38 -4.7(3) . . . . ? C42 C37 C38 C39 -1.5(3) . . . . ? C36 C37 C38 C39 178.5(2) . . . . ? F38 C38 C39 F39 0.5(3) . . . . ? C37 C38 C39 F39 177.4(2) . . . . ? F38 C38 C39 C40 -178.20(19) . . . . ? C37 C38 C39 C40 -1.3(3) . . . . ? F39 C39 C40 F40 2.2(3) . . . . ? C38 C39 C40 F40 -179.16(19) . . . . ? F39 C39 C40 C41 -175.8(2) . . . . ? C38 C39 C40 C41 2.8(3) . . . . ? F40 C40 C41 F41 0.8(3) . . . . ? C39 C40 C41 F41 178.82(19) . . . . ? F40 C40 C41 C42 -179.54(19) . . . . ? C39 C40 C41 C42 -1.5(4) . . . . ? F41 C41 C42 F42 -0.7(3) . . . . ? C40 C41 C42 F42 179.7(2) . . . . ? F41 C41 C42 C37 178.2(2) . . . . ? C40 C41 C42 C37 -1.4(4) . . . . ? C38 C37 C42 F42 -178.24(19) . . . . ? C36 C37 C42 F42 1.7(3) . . . . ? C38 C37 C42 C41 2.9(3) . . . . ? C36 C37 C42 C41 -177.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.214 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.043 data_03002a _database_code_CSD 203759 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 03002a _chemical_melting_point ? _chemical_formula_moiety 'C21 H20' _chemical_formula_sum 'C21 H20' _chemical_formula_weight 272.37 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0081(8) _cell_length_b 11.5316(15) _cell_length_c 22.082(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.343(2) _cell_angle_gamma 90.00 _cell_volume 1529.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4009 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details 'Prof. Jin Liu - Murray State University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-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 18573 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3507 _reflns_number_gt 3130 _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^)+(0.0471P)^2^+0.4421P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3507 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.45712(19) 0.46746(10) 0.27600(5) 0.0275(2) Uani 1 1 d . . . C2 C 0.37032(19) 0.58810(10) 0.28951(5) 0.0289(3) Uani 1 1 d . . . H2A H 0.3029 0.6302 0.2540 0.035 Uiso 1 1 calc R . . C3 C 0.22057(19) 0.57916(11) 0.34550(5) 0.0305(3) Uani 1 1 d . . . H3A H 0.1129 0.5146 0.3410 0.037 Uiso 1 1 calc R . . H3B H 0.1381 0.6523 0.3520 0.037 Uiso 1 1 calc R . . C4 C 0.3899(2) 0.55584(11) 0.39837(5) 0.0321(3) Uani 1 1 d . . . H4A H 0.3890 0.6196 0.4284 0.039 Uiso 1 1 calc R . . H4B H 0.3568 0.4819 0.4191 0.039 Uiso 1 1 calc R . . C5 C 0.61588(19) 0.54970(10) 0.36610(5) 0.0278(2) Uani 1 1 d . . . H5A H 0.7505 0.5598 0.3931 0.033 Uiso 1 1 calc R . . C6 C 0.61485(19) 0.44106(10) 0.32718(5) 0.0268(2) Uani 1 1 d . . . C7 C 0.5822(2) 0.64398(11) 0.31746(6) 0.0318(3) Uani 1 1 d . . . H7A H 0.7062 0.6476 0.2888 0.038 Uiso 1 1 calc R . . H7B H 0.5544 0.7216 0.3349 0.038 Uiso 1 1 calc R . . C8 C 0.4116(2) 0.40064(11) 0.22755(5) 0.0315(3) Uani 1 1 d . . . H8A H 0.4939 0.3306 0.2246 0.038 Uiso 1 1 calc R . . C9 C 0.2479(2) 0.42410(10) 0.17836(5) 0.0308(3) Uani 1 1 d . . . C10 C 0.2940(2) 0.38931(11) 0.11897(5) 0.0341(3) Uani 1 1 d . . . H10A H 0.4334 0.3545 0.1108 0.041 Uiso 1 1 calc R . . C11 C 0.1390(2) 0.40504(12) 0.07216(6) 0.0408(3) Uani 1 1 d . . . H11A H 0.1726 0.3809 0.0323 0.049 Uiso 1 1 calc R . . C12 C -0.0649(2) 0.45588(12) 0.08351(6) 0.0422(3) Uani 1 1 d . . . H12A H -0.1709 0.4667 0.0514 0.051 Uiso 1 1 calc R . . C13 C -0.1140(2) 0.49097(12) 0.14181(6) 0.0394(3) Uani 1 1 d . . . H13A H -0.2533 0.5263 0.1496 0.047 Uiso 1 1 calc R . . C14 C 0.0402(2) 0.47452(11) 0.18882(6) 0.0352(3) Uani 1 1 d . . . H14A H 0.0043 0.4978 0.2287 0.042 Uiso 1 1 calc R . . C15 C 0.7309(2) 0.34314(11) 0.33575(5) 0.0324(3) Uani 1 1 d . . . H15A H 0.7117 0.2848 0.3057 0.039 Uiso 1 1 calc R . . C16 C 0.8850(2) 0.31583(10) 0.38660(5) 0.0312(3) Uani 1 1 d . . . C17 C 1.0761(3) 0.25034(12) 0.37605(7) 0.0437(3) Uani 1 1 d . . . H17A H 1.1008 0.2215 0.3365 0.052 Uiso 1 1 calc R . . C18 C 1.2299(3) 0.22658(13) 0.42197(7) 0.0489(4) Uani 1 1 d . . . H18A H 1.3599 0.1831 0.4136 0.059 Uiso 1 1 calc R . . C19 C 1.1947(2) 0.26610(12) 0.48012(7) 0.0425(3) Uani 1 1 d . . . H19A H 1.3004 0.2503 0.5117 0.051 Uiso 1 1 calc R . . C20 C 1.0047(2) 0.32872(13) 0.49186(6) 0.0407(3) Uani 1 1 d . . . H20A H 0.9793 0.3555 0.5318 0.049 Uiso 1 1 calc R . . C21 C 0.8504(2) 0.35288(12) 0.44582(5) 0.0354(3) Uani 1 1 d . . . H21A H 0.7194 0.3952 0.4547 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0278(5) 0.0299(6) 0.0247(5) 0.0011(4) 0.0028(4) -0.0006(4) C2 0.0306(6) 0.0281(6) 0.0279(6) 0.0026(4) -0.0003(4) 0.0002(5) C3 0.0271(6) 0.0312(6) 0.0333(6) -0.0026(5) 0.0023(5) 0.0017(5) C4 0.0323(6) 0.0368(6) 0.0274(6) -0.0033(5) 0.0039(5) 0.0041(5) C5 0.0263(5) 0.0298(6) 0.0272(6) -0.0039(4) -0.0003(4) 0.0007(4) C6 0.0272(5) 0.0306(6) 0.0228(5) -0.0019(4) 0.0024(4) -0.0016(4) C7 0.0307(6) 0.0292(6) 0.0357(6) -0.0001(5) 0.0025(5) -0.0029(5) C8 0.0337(6) 0.0327(6) 0.0282(6) -0.0020(5) 0.0004(5) 0.0005(5) C9 0.0360(6) 0.0292(6) 0.0272(6) -0.0002(5) -0.0026(5) -0.0072(5) C10 0.0422(7) 0.0304(6) 0.0295(6) -0.0008(5) 0.0002(5) -0.0087(5) C11 0.0574(8) 0.0370(7) 0.0278(6) 0.0009(5) -0.0045(6) -0.0149(6) C12 0.0504(8) 0.0375(7) 0.0378(7) 0.0084(6) -0.0165(6) -0.0128(6) C13 0.0353(7) 0.0364(7) 0.0460(7) 0.0051(6) -0.0071(6) -0.0069(5) C14 0.0365(6) 0.0365(7) 0.0326(6) -0.0012(5) -0.0013(5) -0.0051(5) C15 0.0387(6) 0.0311(6) 0.0273(6) -0.0041(5) 0.0002(5) 0.0023(5) C16 0.0348(6) 0.0264(6) 0.0323(6) 0.0016(5) 0.0003(5) 0.0021(5) C17 0.0529(8) 0.0361(7) 0.0421(7) -0.0049(6) 0.0015(6) 0.0165(6) C18 0.0455(8) 0.0415(8) 0.0595(9) 0.0035(7) -0.0004(7) 0.0206(6) C19 0.0390(7) 0.0417(7) 0.0464(8) 0.0118(6) -0.0076(6) 0.0059(6) C20 0.0401(7) 0.0509(8) 0.0309(6) 0.0068(6) -0.0009(5) 0.0051(6) C21 0.0310(6) 0.0442(7) 0.0311(6) 0.0038(5) 0.0029(5) 0.0075(5) _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 C8 1.3414(16) . ? C1 C6 1.4892(15) . ? C1 C2 1.5178(16) . ? C2 C7 1.5426(17) . ? C2 C3 1.5493(16) . ? C2 H2A 1.0000 . ? C3 C4 1.5539(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5497(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5192(15) . ? C5 C7 1.5383(17) . ? C5 H5A 1.0000 . ? C6 C15 1.3382(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.4733(16) . ? C8 H8A 0.9500 . ? C9 C14 1.4008(18) . ? C9 C10 1.4050(17) . ? C10 C11 1.3868(18) . ? C10 H10A 0.9500 . ? C11 C12 1.386(2) . ? C11 H11A 0.9500 . ? C12 C13 1.388(2) . ? C12 H12A 0.9500 . ? C13 C14 1.3881(18) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.4726(17) . ? C15 H15A 0.9500 . ? C16 C21 1.3960(17) . ? C16 C17 1.3982(18) . ? C17 C18 1.383(2) . ? C17 H17A 0.9500 . ? C18 C19 1.383(2) . ? C18 H18A 0.9500 . ? C19 C20 1.380(2) . ? C19 H19A 0.9500 . ? C20 C21 1.3881(17) . ? C20 H20A 0.9500 . ? C21 H21A 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 C8 C1 C6 127.01(11) . . ? C8 C1 C2 128.23(11) . . ? C6 C1 C2 104.69(9) . . ? C1 C2 C7 100.22(9) . . ? C1 C2 C3 107.73(9) . . ? C7 C2 C3 101.40(9) . . ? C1 C2 H2A 115.2 . . ? C7 C2 H2A 115.2 . . ? C3 C2 H2A 115.2 . . ? C2 C3 C4 103.23(9) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C5 C4 C3 103.16(9) . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4B 111.1 . . ? C3 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? C6 C5 C7 100.90(9) . . ? C6 C5 C4 107.81(9) . . ? C7 C5 C4 100.74(9) . . ? C6 C5 H5A 115.2 . . ? C7 C5 H5A 115.2 . . ? C4 C5 H5A 115.2 . . ? C15 C6 C1 126.87(11) . . ? C15 C6 C5 128.36(11) . . ? C1 C6 C5 104.77(9) . . ? C5 C7 C2 94.47(9) . . ? C5 C7 H7A 112.8 . . ? C2 C7 H7A 112.8 . . ? C5 C7 H7B 112.8 . . ? C2 C7 H7B 112.8 . . ? H7A C7 H7B 110.3 . . ? C1 C8 C9 127.05(12) . . ? C1 C8 H8A 116.5 . . ? C9 C8 H8A 116.5 . . ? C14 C9 C10 117.91(11) . . ? C14 C9 C8 122.45(11) . . ? C10 C9 C8 119.54(12) . . ? C11 C10 C9 120.99(13) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C12 C11 C10 120.10(13) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? C11 C12 C13 119.92(12) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 120.09(13) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C14 C9 121.00(12) . . ? C13 C14 H14A 119.5 . . ? C9 C14 H14A 119.5 . . ? C6 C15 C16 127.19(11) . . ? C6 C15 H15A 116.4 . . ? C16 C15 H15A 116.4 . . ? C21 C16 C17 117.54(12) . . ? C21 C16 C15 122.94(11) . . ? C17 C16 C15 119.51(11) . . ? C18 C17 C16 121.47(13) . . ? C18 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C17 C18 C19 120.06(13) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C20 C19 C18 119.46(12) . . ? C20 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C19 C20 C21 120.57(13) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C16 120.86(12) . . ? C20 C21 H21A 119.6 . . ? C16 C21 H21A 119.6 . . ? 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 C1 C2 C7 -140.91(12) . . . . ? C6 C1 C2 C7 36.26(11) . . . . ? C8 C1 C2 C3 113.51(13) . . . . ? C6 C1 C2 C3 -69.32(11) . . . . ? C1 C2 C3 C4 70.96(11) . . . . ? C7 C2 C3 C4 -33.79(11) . . . . ? C2 C3 C4 C5 -1.98(12) . . . . ? C3 C4 C5 C6 -68.09(11) . . . . ? C3 C4 C5 C7 37.16(11) . . . . ? C8 C1 C6 C15 -3.9(2) . . . . ? C2 C1 C6 C15 178.90(12) . . . . ? C8 C1 C6 C5 175.31(12) . . . . ? C2 C1 C6 C5 -1.90(11) . . . . ? C7 C5 C6 C15 145.87(12) . . . . ? C4 C5 C6 C15 -108.99(13) . . . . ? C7 C5 C6 C1 -33.31(11) . . . . ? C4 C5 C6 C1 71.83(11) . . . . ? C6 C5 C7 C2 53.82(10) . . . . ? C4 C5 C7 C2 -56.88(10) . . . . ? C1 C2 C7 C5 -54.87(10) . . . . ? C3 C2 C7 C5 55.74(10) . . . . ? C6 C1 C8 C9 176.86(11) . . . . ? C2 C1 C8 C9 -6.6(2) . . . . ? C1 C8 C9 C14 -38.42(19) . . . . ? C1 C8 C9 C10 145.24(13) . . . . ? C14 C9 C10 C11 0.35(18) . . . . ? C8 C9 C10 C11 176.86(11) . . . . ? C9 C10 C11 C12 0.10(19) . . . . ? C10 C11 C12 C13 -0.06(19) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 C9 0.9(2) . . . . ? C10 C9 C14 C13 -0.85(18) . . . . ? C8 C9 C14 C13 -177.25(12) . . . . ? C1 C6 C15 C16 -179.20(11) . . . . ? C5 C6 C15 C16 1.8(2) . . . . ? C6 C15 C16 C21 35.7(2) . . . . ? C6 C15 C16 C17 -144.09(14) . . . . ? C21 C16 C17 C18 -2.4(2) . . . . ? C15 C16 C17 C18 177.39(13) . . . . ? C16 C17 C18 C19 1.1(2) . . . . ? C17 C18 C19 C20 0.3(2) . . . . ? C18 C19 C20 C21 -0.5(2) . . . . ? C19 C20 C21 C16 -0.8(2) . . . . ? C17 C16 C21 C20 2.2(2) . . . . ? C15 C16 C21 C20 -177.53(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.251 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.034