#============================================================================== data_global _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Yuji Hanzawa' _publ_contact_author_address ; Department of Medicinal Chemistry, Showa Pharmaceutical University, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan ; _publ_contact_author_email hanzaway@ac.shoyaku.ac.jp _publ_contact_author_phone ? _publ_contact_author_fax ? loop_ _publ_author_name _publ_author_address 'Yutaka Ikeuchi, Takeo Taguchi' ; School of Pharmacy Tokyo University of Pharmacy and Life Science 1432-1 Horinouchi Hachioji Tokyo Japan 192-0392 ; 'Yuji Hanzawa' ; Department of Medicinal Chemistry, Showa Pharmaceutical University, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan ; #============================================================================== _audit_creation_date 2005-02-01 _audit_creation_method 'SHELXL97 ' _publ_requested_category ? _publ_contact_letter ; ? ; _publ_section_title ; Zirconocene-Mediated and/or Catalyzed Unprecedented Coupling Reactions of Alkoxymethyl-Substituted Styrene Derivatives ; _publ_section_abstract ; Reactions of o-(alkoxymethyl)styrene derivatives with a stoichiometric amount of zirconocene-butene complex (zirconocene equivalent, ?Cp2Zr?) brought about an insertion of the zirconocene species into a benzylic carbon-oxygen bond. The oxidative insertion of Cp2Zr to the benzylic carbon-oxygen bond is a result of sequential reactions; i) formation of zirconacyclopropane by the ligand exchange with o-(alkoxymethyl)styrene, ii) elimination of the alkoxy group through an aromatic conjugate system giving metalated o-quinodimethane species, and iii) transfer of zirconium metal to the benzylic position. Through use of a catalytic amount of ?Cp2Zr?, however, unprecedented homo-coupling reactions (dimerization) of o-(alkoxymethyl)styrene derivatives occurred to give a tetracyclic compound. On the other hand, reactions of o-(1-alkoxy-isopropyl)styrene derivatives gave rise to the analogous tetracyclic compounds regardless of the amount of ?Cp2Zr? (stoichiometric or catalytic). Hetero-coupling product between o-(1-alkoxy-isopropyl)styrene and styrene congeners was obtained in cis stereo- and regioselectivity by treating o-(1-alkoxy-isopropyl)styrene derivatives with ?Cp2Zr? in the presence of an excess amount of styrene derivatives. ; _publ_section_comment ; ? ; #============================================================================== # TEXT _publ_section_acknowledgements ; ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; #============================================================================== data_19a #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; trans-6,6,12,12-Tetramethyl-4b,5,6,10b,11,12-hexahydrochrysene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26' _chemical_formula_sum 'C22 H26' _chemical_formula_weight 290.43 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' 'O' 'O' 0.0106 0.0060 '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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6720(13) _cell_length_b 9.7210(10) _cell_length_c 11.1550(17) _cell_angle_alpha 103.884(8) _cell_angle_beta 101.898(7) _cell_angle_gamma 107.401(7) _cell_volume 831.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316.0 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_measurement_device_type 'Mac Science DIP2000' _diffrn_measurement_method ' phi scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3434 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.23 _reflns_number_total 3434 _reflns_number_gt 2291 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.1180P)^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 SHELXL _refine_ls_extinction_coef 0.15(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3434 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1657(2) 0.4446(2) 0.5809(2) 0.0270(4) Uani 1 1 d . . . H1 H 0.0908 0.4082 0.4954 0.032 Uiso 1 1 calc R . . C2 C 0.0991(2) 0.4456(2) 0.68267(19) 0.0264(4) Uani 1 1 d . . . H2 H -0.0202 0.4104 0.6671 0.032 Uiso 1 1 calc R . . C3 C 0.2061(2) 0.4979(2) 0.8075(2) 0.0267(4) Uani 1 1 d . . . H3 H 0.1610 0.4979 0.8782 0.032 Uiso 1 1 calc R . . C4 C 0.3800(2) 0.55046(19) 0.82892(18) 0.0235(4) Uani 1 1 d . . . H4 H 0.4531 0.5865 0.9151 0.028 Uiso 1 1 calc R . . C5 C 0.4508(2) 0.55177(19) 0.72667(18) 0.0223(4) Uani 1 1 d . . . C6 C 0.3410(2) 0.4956(2) 0.59956(18) 0.0229(4) Uani 1 1 d . . . C7 C 0.4093(3) 0.4994(4) 0.4841(2) 0.0193(6) Uani 0.830(7) 1 d P . 3 H7 H 0.4118 0.5953 0.4650 0.023 Uiso 1 1 calc R . 3 C8 C 0.3016(3) 0.3642(2) 0.3610(2) 0.0209(7) Uani 0.830(7) 1 d P A 3 H8A H 0.1810 0.3524 0.3455 0.025 Uiso 1 1 calc R A 3 H8B H 0.3125 0.2698 0.3737 0.025 Uiso 1 1 calc R A 3 C9 C 0.3562(2) 0.3861(2) 0.24137(19) 0.0256(4) Uani 1 1 d . . . C10 C 0.2827(3) 0.4895(2) 0.1833(2) 0.0344(5) Uani 1 1 d . A . H10A H 0.3266 0.5918 0.2467 0.041 Uiso 1 1 calc R . . H10B H 0.1589 0.4475 0.1608 0.041 Uiso 1 1 calc R . . H10C H 0.3159 0.4950 0.1052 0.041 Uiso 1 1 calc R . . C11 C 0.2803(3) 0.2256(2) 0.1419(2) 0.0359(5) Uani 1 1 d . A . H11A H 0.3011 0.2308 0.0597 0.043 Uiso 1 1 calc R . . H11B H 0.1580 0.1833 0.1285 0.043 Uiso 1 1 calc R . . H11C H 0.3333 0.1601 0.1739 0.043 Uiso 1 1 calc R . . C12 C 0.7004(3) 0.0839(2) 0.4551(2) 0.0215(7) Uani 0.830(7) 1 d P . 1 H12A H 0.8200 0.1001 0.4954 0.026 Uiso 1 1 calc R . 1 H12B H 0.6917 0.1850 0.4651 0.026 Uiso 1 1 calc R . 1 C13 C 0.5889(3) 0.0002(4) 0.5249(2) 0.0191(6) Uani 0.830(7) 1 d P . 1 H13 H 0.5823 -0.1078 0.5003 0.023 Uiso 1 1 calc R . 1 C14 C 0.6557(2) 0.06804(19) 0.67221(18) 0.0230(4) Uani 1 1 d . . . C15 C 0.8304(2) 0.1235(2) 0.7349(2) 0.0278(4) Uani 1 1 d . A . H15 H 0.9053 0.1216 0.6838 0.033 Uiso 1 1 calc R . . C16 C 0.8973(2) 0.1803(2) 0.8675(2) 0.0289(5) Uani 1 1 d . . . H16 H 1.0162 0.2164 0.9068 0.035 Uiso 1 1 calc R A . C17 C 0.7902(3) 0.1845(2) 0.9431(2) 0.0292(5) Uani 1 1 d . A . H17 H 0.8347 0.2251 1.0348 0.035 Uiso 1 1 calc R . . C18 C 0.6164(3) 0.12871(19) 0.88364(18) 0.0255(4) Uani 1 1 d . . . H18 H 0.5434 0.1314 0.9363 0.031 Uiso 1 1 calc R A . C19 C 0.5453(2) 0.06868(18) 0.74904(18) 0.0214(4) Uani 1 1 d . . . C20 C 0.6468(2) -0.0072(2) 0.30917(19) 0.0238(4) Uani 1 1 d . . . C21 C 0.7125(3) -0.1369(2) 0.2849(3) 0.0425(6) Uani 1 1 d . . 5 H21A H 0.6614 -0.2106 0.3253 0.064 Uiso 1 1 calc R . 5 H21B H 0.8360 -0.0962 0.3224 0.064 Uiso 1 1 calc R . 5 H21C H 0.6824 -0.1873 0.1915 0.064 Uiso 1 1 calc R . 5 C22 C 0.7325(3) 0.1080(2) 0.2475(2) 0.0407(6) Uani 1 1 d . . . H22A H 0.7101 0.0564 0.1552 0.061 Uiso 1 1 calc R . . H22B H 0.8549 0.1514 0.2904 0.061 Uiso 1 1 calc R . . H22C H 0.6870 0.1897 0.2576 0.061 Uiso 1 1 calc R . . C23 C 0.4104(18) 0.4489(18) 0.4825(14) 0.024(4) Uiso 0.170(7) 1 d P . 2 C24 C 0.3061(17) 0.4678(15) 0.3643(13) 0.035(4) Uiso 0.170(7) 1 d P A 2 C25 C 0.5926(17) 0.0521(17) 0.5248(13) 0.020(4) Uiso 0.170(7) 1 d P . 4 C26 C 0.6939(16) -0.0141(16) 0.4491(13) 0.033(4) Uiso 0.170(7) 1 d P . 4 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 0.0241(10) 0.0315(10) 0.0257(11) 0.0087(8) 0.0068(8) 0.0116(8) C2 0.0200(10) 0.0281(9) 0.0316(12) 0.0105(8) 0.0089(8) 0.0082(7) C3 0.0297(11) 0.0256(9) 0.0289(11) 0.0101(8) 0.0138(9) 0.0113(8) C4 0.0266(10) 0.0218(8) 0.0230(10) 0.0064(7) 0.0081(8) 0.0102(7) C5 0.0233(10) 0.0222(8) 0.0226(10) 0.0075(7) 0.0064(8) 0.0099(7) C6 0.0190(9) 0.0256(8) 0.0239(10) 0.0081(7) 0.0067(8) 0.0077(7) C7 0.0195(13) 0.0184(13) 0.0204(13) 0.0063(10) 0.0040(9) 0.0088(10) C8 0.0197(12) 0.0213(13) 0.0208(13) 0.0077(9) 0.0050(9) 0.0060(9) C9 0.0227(10) 0.0312(9) 0.0209(10) 0.0075(8) 0.0041(8) 0.0094(8) C10 0.0269(11) 0.0276(10) 0.0478(14) 0.0141(9) 0.0051(10) 0.0112(8) C11 0.0291(11) 0.0270(10) 0.0478(14) 0.0130(9) 0.0044(10) 0.0093(8) C12 0.0199(12) 0.0206(13) 0.0243(13) 0.0077(9) 0.0073(9) 0.0070(8) C13 0.0182(13) 0.0200(13) 0.0221(13) 0.0100(10) 0.0073(9) 0.0080(10) C14 0.0214(10) 0.0241(8) 0.0242(11) 0.0084(7) 0.0068(8) 0.0088(7) C15 0.0180(9) 0.0351(10) 0.0277(11) 0.0124(8) 0.0052(8) 0.0057(8) C16 0.0214(10) 0.0312(10) 0.0284(11) 0.0122(8) 0.0011(8) 0.0039(8) C17 0.0306(11) 0.0247(9) 0.0242(11) 0.0071(8) 0.0029(9) 0.0031(8) C18 0.0309(11) 0.0230(8) 0.0223(10) 0.0066(7) 0.0098(8) 0.0087(8) C19 0.0228(10) 0.0195(8) 0.0237(10) 0.0080(7) 0.0086(8) 0.0086(7) C20 0.0233(10) 0.0279(9) 0.0240(10) 0.0097(7) 0.0111(8) 0.0108(8) C21 0.0282(12) 0.0326(11) 0.0656(18) 0.0092(10) 0.0131(11) 0.0156(9) C22 0.0333(12) 0.0354(11) 0.0517(16) 0.0212(10) 0.0098(11) 0.0066(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.375(3) . ? C1 C6 1.403(3) . ? C1 H1 0.9500 . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.403(3) . ? C4 H4 0.9500 . ? C5 C6 1.406(3) . ? C5 C9 1.529(3) 2_666 ? C6 C7 1.528(3) . ? C6 C23 1.574(15) . ? C7 C8 1.534(3) . ? C7 C7 1.535(5) 2_666 ? C7 H7 1.0000 . ? C8 C9 1.546(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C5 1.529(3) 2_666 ? C9 C11 1.534(3) . ? C9 C10 1.536(3) . ? C9 C24 1.622(13) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.532(3) . ? C12 C20 1.549(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C13 1.526(5) 2_656 ? C13 C14 1.527(3) . ? C13 H13 1.0000 . ? C14 C15 1.403(3) . ? C14 C19 1.411(3) . ? C14 C25 1.576(14) . ? C15 C16 1.376(3) . ? C15 H15 0.9500 . ? C16 C17 1.380(3) . ? C16 H16 0.9500 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.399(3) . ? C18 H18 0.9500 . ? C19 C20 1.525(3) 2_656 ? C20 C21 1.522(3) . ? C20 C19 1.525(3) 2_656 ? C20 C22 1.537(3) . ? C20 C26 1.553(13) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C23 1.48(3) 2_666 ? C23 C24 1.52(2) . ? C25 C26 1.510(19) . ? C25 C25 1.52(3) 2_656 ? 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 C6 121.99(19) . . ? C2 C1 H1 119.0 . . ? C6 C1 H1 119.0 . . ? C1 C2 C3 119.75(18) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.51(18) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 121.72(18) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 118.43(17) . . ? C4 C5 C9 118.50(16) . 2_666 ? C6 C5 C9 123.07(17) . 2_666 ? C1 C6 C5 118.58(17) . . ? C1 C6 C7 120.11(18) . . ? C5 C6 C7 121.19(17) . . ? C1 C6 C23 119.8(6) . . ? C5 C6 C23 119.5(6) . . ? C7 C6 C23 18.1(5) . . ? C6 C7 C8 113.5(2) . . ? C6 C7 C7 110.7(2) . 2_666 ? C8 C7 C7 107.8(3) . 2_666 ? C6 C7 H7 108.2 . . ? C8 C7 H7 108.2 . . ? C7 C7 H7 108.2 2_666 . ? C7 C8 C9 111.83(18) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C5 C9 C11 110.31(15) 2_666 . ? C5 C9 C10 109.91(15) 2_666 . ? C11 C9 C10 108.23(16) . . ? C5 C9 C8 111.19(16) 2_666 . ? C11 C9 C8 104.27(16) . . ? C10 C9 C8 112.75(17) . . ? C5 C9 C24 108.5(5) 2_666 . ? C11 C9 C24 133.4(5) . . ? C10 C9 C24 81.2(5) . . ? C8 C9 C24 36.2(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C20 111.48(18) . . ? C13 C12 H12A 109.3 . . ? C20 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C20 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C13 C13 C14 110.7(2) 2_656 . ? C13 C13 C12 107.8(3) 2_656 . ? C14 C13 C12 113.9(2) . . ? C13 C13 H13 108.1 2_656 . ? C14 C13 H13 108.1 . . ? C12 C13 H13 108.1 . . ? C15 C14 C19 118.27(17) . . ? C15 C14 C13 120.00(17) . . ? C19 C14 C13 121.62(17) . . ? C15 C14 C25 119.0(5) . . ? C19 C14 C25 120.4(5) . . ? C13 C14 C25 18.3(5) . . ? C16 C15 C14 122.54(19) . . ? C16 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C15 C16 C17 119.46(18) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 119.24(18) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 122.35(18) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C14 118.11(17) . . ? C18 C19 C20 119.36(16) . 2_656 ? C14 C19 C20 122.53(16) . 2_656 ? C21 C20 C19 110.10(15) . 2_656 ? C21 C20 C22 108.11(17) . . ? C19 C20 C22 110.75(16) 2_656 . ? C21 C20 C12 112.00(18) . . ? C19 C20 C12 110.90(16) 2_656 . ? C22 C20 C12 104.84(17) . . ? C21 C20 C26 81.0(5) . . ? C19 C20 C26 110.0(5) 2_656 . ? C22 C20 C26 131.4(5) . . ? C12 C20 C26 34.6(5) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 C23 C24 109.7(16) 2_666 . ? C23 C23 C6 108.3(14) 2_666 . ? C24 C23 C6 108.8(11) . . ? C23 C24 C9 106.6(10) . . ? C26 C25 C25 110.6(15) . 2_656 ? C26 C25 C14 111.2(10) . . ? C25 C25 C14 106.5(13) 2_656 . ? C25 C26 C20 110.0(10) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.23 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.435 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.058 #============================================================================== data_19b #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; trans-2,8-Dimethoxy-6,6,12,12-tetramethyl-4b,5,6,10b,11,12-hexahydrochrysene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 O2' _chemical_formula_sum 'C24 H30 O2' _chemical_formula_weight 350.48 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/C ' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.7970(2) _cell_length_b 13.7220(9) _cell_length_c 11.8190(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.498(4) _cell_angle_gamma 90.00 _cell_volume 938.41(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1982 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 27.16 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _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 'Mac Science DIP2000' _diffrn_measurement_method ' phi scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1982 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.16 _reflns_number_total 1982 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.1063P)^2^+0.3055P] 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 1982 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.6717(3) 0.56640(12) 0.18732(14) 0.0163(4) Uani 1 1 d . . . H1 H 0.6830 0.6341 0.1718 0.020 Uiso 1 1 calc R . . C2 C 0.5241(3) 0.53597(12) 0.26918(14) 0.0168(4) Uani 1 1 d . . . H2 H 0.4361 0.5821 0.3083 0.020 Uiso 1 1 calc R . . C3 C 0.5079(3) 0.43729(13) 0.29254(13) 0.0153(4) Uani 1 1 d . . . C4 C 0.6369(3) 0.37073(12) 0.23360(14) 0.0154(4) Uani 1 1 d . . . H4 H 0.6241 0.3032 0.2498 0.018 Uiso 1 1 calc R . . C5 C 0.7848(3) 0.40092(12) 0.15119(14) 0.0154(4) Uani 1 1 d . . . C6 C 0.8041(3) 0.50127(12) 0.12706(13) 0.0155(4) Uani 1 1 d . . . C7 C 0.9132(3) 0.32263(12) 0.08726(14) 0.0175(4) Uani 1 1 d . . . C8 C 1.1059(3) 0.36863(13) 0.01974(15) 0.0206(4) Uani 1 1 d . . . H8A H 1.2401 0.3840 0.0726 0.025 Uiso 1 1 calc R . . H8B H 1.1571 0.3205 -0.0359 0.025 Uiso 1 1 calc R . . C9 C 1.0286(3) 0.46082(12) -0.04253(14) 0.0181(4) Uani 1 1 d . . . H9 H 0.8812 0.4448 -0.0869 0.022 Uiso 1 1 calc R . . C10 C 0.7391(3) 0.26667(13) 0.00923(15) 0.0228(4) Uani 1 1 d . . . H10A H 0.6240 0.2356 0.0548 0.034 Uiso 1 1 calc R . . H10B H 0.8203 0.2167 -0.0322 0.034 Uiso 1 1 calc R . . H10C H 0.6617 0.3120 -0.0448 0.034 Uiso 1 1 calc R . . C11 C 1.0364(3) 0.25029(13) 0.17007(15) 0.0225(4) Uani 1 1 d . . . H11A H 1.1372 0.2861 0.2251 0.034 Uiso 1 1 calc R . . H11B H 1.1294 0.2050 0.1278 0.034 Uiso 1 1 calc R . . H11C H 0.9211 0.2137 0.2100 0.034 Uiso 1 1 calc R . . C12 C 0.2060(3) 0.46162(14) 0.41867(16) 0.0227(4) Uani 1 1 d . . . H12A H 0.2880 0.5134 0.4618 0.034 Uiso 1 1 calc R . . H12B H 0.1104 0.4246 0.4691 0.034 Uiso 1 1 calc R . . H12C H 0.1071 0.4906 0.3574 0.034 Uiso 1 1 calc R . . O13 O 0.37008(19) 0.39774(9) 0.37155(10) 0.0205(3) 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 0.0178(8) 0.0142(8) 0.0171(8) -0.0014(6) 0.0026(6) 0.0005(6) C2 0.0167(8) 0.0174(9) 0.0164(8) -0.0024(6) 0.0031(6) 0.0016(6) C3 0.0128(8) 0.0198(9) 0.0135(8) 0.0007(6) 0.0016(6) -0.0008(6) C4 0.0157(8) 0.0145(8) 0.0161(8) 0.0007(6) 0.0011(6) 0.0003(6) C5 0.0156(8) 0.0159(8) 0.0146(8) -0.0003(6) 0.0013(6) 0.0010(6) C6 0.0158(8) 0.0154(8) 0.0155(8) -0.0010(6) 0.0022(6) 0.0016(6) C7 0.0204(8) 0.0128(8) 0.0199(9) 0.0005(6) 0.0053(6) 0.0018(6) C8 0.0218(9) 0.0187(9) 0.0216(9) 0.0012(7) 0.0034(6) 0.0028(6) C9 0.0207(8) 0.0145(8) 0.0199(9) 0.0005(7) 0.0071(6) 0.0006(6) C10 0.0252(9) 0.0208(9) 0.0219(9) -0.0046(7) -0.0037(7) 0.0052(7) C11 0.0188(9) 0.0218(9) 0.0266(9) -0.0025(7) -0.0002(7) 0.0040(6) C12 0.0216(9) 0.0244(9) 0.0232(9) -0.0012(7) 0.0098(7) 0.0021(7) O13 0.0215(7) 0.0197(7) 0.0214(7) 0.0021(5) 0.0104(5) 0.0021(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 C2 1.394(2) . ? C1 C6 1.401(2) . ? C1 H1 0.9500 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 O13 1.3769(19) . ? C3 C4 1.394(2) . ? C4 C5 1.399(2) . ? C4 H4 0.9500 . ? C5 C6 1.412(2) . ? C5 C7 1.532(2) . ? C6 C9 1.525(2) 3_765 ? C7 C10 1.531(2) . ? C7 C11 1.539(2) . ? C7 C8 1.547(2) . ? C8 C9 1.517(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C9 1.522(3) 3_765 ? C9 C6 1.525(2) 3_765 ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O13 1.4312(19) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C6 122.71(15) . . ? C2 C1 H1 118.6 . . ? C6 C1 H1 118.6 . . ? C3 C2 C1 118.85(15) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? O13 C3 C2 124.69(14) . . ? O13 C3 C4 115.59(15) . . ? C2 C3 C4 119.71(15) . . ? C3 C4 C5 121.63(15) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 119.26(14) . . ? C4 C5 C7 118.20(14) . . ? C6 C5 C7 122.49(14) . . ? C1 C6 C5 117.83(14) . . ? C1 C6 C9 120.36(15) . 3_765 ? C5 C6 C9 121.75(14) . 3_765 ? C5 C7 C10 109.05(13) . . ? C5 C7 C11 111.05(14) . . ? C10 C7 C11 108.83(14) . . ? C5 C7 C8 110.87(14) . . ? C10 C7 C8 111.35(14) . . ? C11 C7 C8 105.64(13) . . ? C9 C8 C7 112.90(13) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C9 109.78(18) . 3_765 ? C8 C9 C6 114.91(14) . 3_765 ? C9 C9 C6 111.38(17) 3_765 3_765 ? C8 C9 H9 106.8 . . ? C9 C9 H9 106.8 3_765 . ? C6 C9 H9 106.8 3_765 . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O13 C12 H12A 109.5 . . ? O13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 O13 C12 116.71(13) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.899 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.069 #============================================================================== data_19c #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; cis-2,8-Difluoro-6,6,12,12-tetramethyl-4b,5,6,10b,11,12-hexahydrochrysene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 F2' _chemical_formula_sum 'C22 H24 F2' _chemical_formula_weight 326.41 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/C ' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.4650(13) _cell_length_b 14.9300(16) _cell_length_c 15.2540(17) _cell_angle_alpha 90.00 _cell_angle_beta 127.363(8) _cell_angle_gamma 90.00 _cell_volume 1713.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3707 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.22 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9637 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mac Science DIP2000' _diffrn_measurement_method ' phi scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3707 _diffrn_reflns_av_R_equivalents 0.056 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.22 _reflns_number_total 3707 _reflns_number_gt 2139 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.1874P)^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_number_reflns 3707 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1323 _refine_ls_R_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.2839 _refine_ls_wR_factor_gt 0.2601 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.1502(5) 0.2822(2) 0.5550(3) 0.0578(9) Uani 1 1 d . . . C2 C 0.2526(4) 0.36966(19) 0.5813(2) 0.0460(7) Uani 1 1 d . . . C3 C 0.3920(4) 0.38722(19) 0.6909(2) 0.0444(7) Uani 1 1 d . . . H3 H 0.4214 0.3453 0.7466 0.053 Uiso 1 1 calc R B . C4 C 0.4874(4) 0.46536(19) 0.7188(2) 0.0462(7) Uani 1 1 d . . . C5 C 0.4529(4) 0.5282(2) 0.6434(2) 0.0484(7) Uani 1 1 d . . . H5 H 0.5207 0.5818 0.6650 0.058 Uiso 1 1 calc R B . C6 C 0.3152(4) 0.5108(2) 0.5343(3) 0.0501(7) Uani 1 1 d . . . H6 H 0.2887 0.5535 0.4801 0.060 Uiso 1 1 calc R . . C7 C 0.2128(4) 0.4323(2) 0.5002(2) 0.0498(7) Uani 1 1 d . . . C8 C 0.0639(5) 0.4160(2) 0.3787(3) 0.0726(11) Uani 1 1 d . B . H8 H 0.1424 0.3982 0.3584 0.087 Uiso 1 1 calc R A 1 C9 C -0.0187(9) 0.4867(4) 0.3046(5) 0.046(2) Uani 0.512(11) 1 d P B 1 H9A H 0.0709 0.5341 0.3281 0.055 Uiso 0.512(11) 1 calc PR B 1 H9B H -0.1106 0.5118 0.3094 0.055 Uiso 0.512(11) 1 calc PR B 1 C10 C -0.1088(4) 0.46348(19) 0.1805(2) 0.0511(8) Uani 1 1 d . . . C11 C -0.2014(4) 0.37141(19) 0.1523(2) 0.0450(7) Uani 1 1 d . B . C12 C -0.3288(3) 0.34929(18) 0.0411(2) 0.0438(7) Uani 1 1 d . . . H12 H -0.3568 0.3904 -0.0149 0.053 Uiso 1 1 calc R B . C13 C -0.4130(4) 0.26805(19) 0.0134(2) 0.0445(7) Uani 1 1 d . B . C14 C -0.3778(4) 0.20576(19) 0.0907(2) 0.0461(7) Uani 1 1 d . . . H14 H -0.4378 0.1498 0.0694 0.055 Uiso 1 1 calc R B . C15 C -0.2521(4) 0.22750(19) 0.2001(2) 0.0484(7) Uani 1 1 d . B . H15 H -0.2257 0.1852 0.2547 0.058 Uiso 1 1 calc R . . C16 C -0.1612(4) 0.31002(19) 0.2343(2) 0.0462(7) Uani 1 1 d . . . C17 C -0.0242(5) 0.3297(2) 0.3549(3) 0.0595(9) Uani 1 1 d . B . H17 H 0.0735 0.2910 0.3684 0.071 Uiso 1 1 calc R C 3 C18 C -0.0415(8) 0.2895(4) 0.4317(4) 0.0475(18) Uani 0.536(9) 1 d P B 3 H18A H -0.0923 0.2287 0.4057 0.057 Uiso 0.536(9) 1 calc PR B 3 H18B H -0.1250 0.3252 0.4364 0.057 Uiso 0.536(9) 1 calc PR B 3 C19 C 0.2713(6) 0.2024(2) 0.5972(4) 0.0896(15) Uani 1 1 d . B . H19A H 0.3561 0.2054 0.6778 0.134 Uiso 1 1 calc R . . H19B H 0.3362 0.2023 0.5659 0.134 Uiso 1 1 calc R . . H19C H 0.2008 0.1475 0.5755 0.134 Uiso 1 1 calc R . . C20 C 0.0586(4) 0.2831(2) 0.6092(3) 0.0689(10) Uani 1 1 d . B . H20A H -0.0199 0.2310 0.5844 0.103 Uiso 1 1 calc R . . H20B H -0.0117 0.3381 0.5885 0.103 Uiso 1 1 calc R . . H20C H 0.1482 0.2809 0.6895 0.103 Uiso 1 1 calc R . . C21 C -0.2479(5) 0.5370(2) 0.1370(3) 0.0671(10) Uani 1 1 d . B . H21A H -0.1885 0.5951 0.1652 0.101 Uiso 1 1 calc R . . H21B H -0.3208 0.5258 0.1616 0.101 Uiso 1 1 calc R . . H21C H -0.3238 0.5374 0.0562 0.101 Uiso 1 1 calc R . . C22 C -0.0185(5) 0.4746(2) 0.1263(4) 0.0792(13) Uani 1 1 d . B . H22A H -0.1064 0.4672 0.0463 0.119 Uiso 1 1 calc R . . H22B H 0.0748 0.4292 0.1551 0.119 Uiso 1 1 calc R . . H22C H 0.0344 0.5344 0.1424 0.119 Uiso 1 1 calc R . . C23 C 0.0692(9) 0.4637(4) 0.2978(5) 0.043(2) Uani 0.488(11) 1 d P B 2 H23A H 0.1617 0.4363 0.2950 0.051 Uiso 0.488(11) 1 calc PR B 2 H23B H 0.1046 0.5265 0.3223 0.051 Uiso 0.488(11) 1 calc PR B 2 C24 C 0.0648(8) 0.2536(4) 0.4339(5) 0.0402(18) Uani 0.464(9) 1 d P B 4 H24A H 0.1583 0.2288 0.4304 0.048 Uiso 0.464(9) 1 calc PR B 4 H24B H -0.0235 0.2058 0.4116 0.048 Uiso 0.464(9) 1 calc PR B 4 F25 F 0.6237(2) 0.47996(13) 0.82796(14) 0.0623(6) Uani 1 1 d . . . F26 F -0.5373(2) 0.24841(11) -0.09532(13) 0.0549(5) 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 0.073(2) 0.0474(16) 0.0458(18) -0.0039(13) 0.0326(17) -0.0206(15) C2 0.0512(16) 0.0409(14) 0.0437(16) -0.0028(12) 0.0276(14) -0.0069(12) C3 0.0467(15) 0.0408(15) 0.0481(17) 0.0001(11) 0.0299(14) 0.0012(11) C4 0.0381(14) 0.0526(16) 0.0388(16) -0.0030(12) 0.0187(13) -0.0033(12) C5 0.0427(15) 0.0462(16) 0.0493(18) 0.0008(12) 0.0244(14) -0.0046(12) C6 0.0482(16) 0.0449(15) 0.0499(18) 0.0035(13) 0.0260(15) -0.0051(13) C7 0.0511(17) 0.0448(15) 0.0445(17) 0.0009(12) 0.0242(14) -0.0092(13) C8 0.086(2) 0.067(2) 0.0462(19) 0.0018(15) 0.0306(18) -0.0392(19) C9 0.047(4) 0.040(3) 0.055(4) 0.002(2) 0.033(3) 0.006(2) C10 0.0578(17) 0.0406(15) 0.0402(16) 0.0034(12) 0.0221(14) -0.0022(13) C11 0.0412(14) 0.0395(14) 0.0467(17) 0.0041(11) 0.0228(13) 0.0043(12) C12 0.0406(14) 0.0426(14) 0.0433(16) 0.0022(11) 0.0228(13) 0.0051(12) C13 0.0347(13) 0.0508(16) 0.0406(16) -0.0067(12) 0.0190(12) -0.0002(11) C14 0.0431(15) 0.0413(15) 0.0503(17) -0.0028(12) 0.0265(14) -0.0028(11) C15 0.0464(15) 0.0411(15) 0.0474(17) 0.0017(12) 0.0231(14) -0.0024(12) C16 0.0441(15) 0.0422(15) 0.0454(17) 0.0024(12) 0.0235(14) -0.0012(12) C17 0.0618(19) 0.0405(16) 0.0476(19) 0.0033(13) 0.0183(16) -0.0094(14) C18 0.049(3) 0.046(3) 0.043(3) -0.002(2) 0.025(3) -0.005(2) C19 0.127(4) 0.0420(19) 0.176(5) -0.016(2) 0.132(4) -0.014(2) C20 0.0555(19) 0.0502(18) 0.106(3) -0.0019(18) 0.052(2) -0.0054(15) C21 0.084(3) 0.0418(17) 0.106(3) -0.0025(16) 0.073(3) 0.0018(16) C22 0.068(2) 0.0469(18) 0.146(4) -0.021(2) 0.077(3) -0.0125(16) C23 0.045(4) 0.035(3) 0.047(4) 0.000(2) 0.027(3) -0.005(2) C24 0.041(3) 0.038(3) 0.045(4) 0.006(2) 0.028(3) 0.000(3) F25 0.0554(11) 0.0697(12) 0.0447(11) -0.0015(8) 0.0214(9) -0.0171(9) F26 0.0531(10) 0.0570(11) 0.0454(11) -0.0058(8) 0.0251(9) -0.0066(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C19 1.500(5) . ? C1 C20 1.519(5) . ? C1 C2 1.527(4) . ? C1 C24 1.560(7) . ? C1 C18 1.643(6) . ? C2 C3 1.389(4) . ? C2 C7 1.407(4) . ? C3 C4 1.375(4) . ? C3 H3 0.9500 . ? C4 C5 1.362(4) . ? C4 F25 1.370(3) . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.403(4) . ? C6 H6 0.9500 . ? C7 C8 1.520(4) . ? C8 C9 1.388(7) . ? C8 C23 1.452(7) . ? C8 C17 1.456(4) . ? C8 H8 1.0000 . ? C9 C10 1.572(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C22 1.517(5) . ? C10 C21 1.522(5) . ? C10 C23 1.543(6) . ? C10 C11 1.544(4) . ? C11 C12 1.399(4) . ? C11 C16 1.405(4) . ? C12 C13 1.370(4) . ? C12 H12 0.9500 . ? C13 F26 1.361(3) . ? C13 C14 1.374(4) . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C15 C16 1.409(4) . ? C15 H15 0.9500 . ? C16 C17 1.502(4) . ? C17 C18 1.413(7) . ? C17 C24 1.490(6) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 C19 C1 C20 108.2(3) . . ? C19 C1 C2 111.6(3) . . ? C20 C1 C2 109.3(3) . . ? C19 C1 C24 90.2(3) . . ? C20 C1 C24 126.1(3) . . ? C2 C1 C24 109.6(3) . . ? C19 C1 C18 124.7(3) . . ? C20 C1 C18 91.3(3) . . ? C2 C1 C18 109.2(3) . . ? C24 C1 C18 40.9(3) . . ? C3 C2 C7 119.0(3) . . ? C3 C2 C1 117.7(3) . . ? C7 C2 C1 123.3(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 F25 118.9(2) . . ? C5 C4 C3 123.2(3) . . ? F25 C4 C3 117.9(3) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 H5 121.5 . . ? C6 C5 H5 121.5 . . ? C5 C6 C7 122.6(3) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C6 C7 C2 118.2(3) . . ? C6 C7 C8 120.4(3) . . ? C2 C7 C8 121.4(3) . . ? C9 C8 C23 39.5(3) . . ? C9 C8 C17 121.0(4) . . ? C23 C8 C17 122.1(4) . . ? C9 C8 C7 121.2(4) . . ? C23 C8 C7 118.2(3) . . ? C17 C8 C7 114.4(3) . . ? C9 C8 H8 96.2 . . ? C23 C8 H8 56.7 . . ? C17 C8 H8 96.2 . . ? C7 C8 H8 96.2 . . ? C8 C9 C10 116.0(5) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C22 C10 C21 107.9(3) . . ? C22 C10 C23 93.0(4) . . ? C21 C10 C23 123.4(4) . . ? C22 C10 C11 110.9(3) . . ? C21 C10 C11 109.0(3) . . ? C23 C10 C11 111.2(3) . . ? C22 C10 C9 124.0(4) . . ? C21 C10 C9 93.4(3) . . ? C23 C10 C9 36.0(3) . . ? C11 C10 C9 109.5(3) . . ? C12 C11 C16 119.6(3) . . ? C12 C11 C10 118.3(2) . . ? C16 C11 C10 122.1(3) . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? F26 C13 C12 118.5(3) . . ? F26 C13 C14 118.7(2) . . ? C12 C13 C14 122.8(3) . . ? C13 C14 C15 117.5(3) . . ? C13 C14 H14 121.3 . . ? C15 C14 H14 121.3 . . ? C14 C15 C16 122.6(3) . . ? C14 C15 H15 118.7 . . ? C16 C15 H15 118.7 . . ? C11 C16 C15 117.8(3) . . ? C11 C16 C17 121.9(3) . . ? C15 C16 C17 120.3(3) . . ? C18 C17 C8 120.4(4) . . ? C18 C17 C24 45.4(3) . . ? C8 C17 C24 121.1(4) . . ? C18 C17 C16 118.9(3) . . ? C8 C17 C16 114.7(3) . . ? C24 C17 C16 119.0(3) . . ? C18 C17 H17 98.2 . . ? C8 C17 H17 98.2 . . ? C24 C17 H17 52.8 . . ? C16 C17 H17 98.2 . . ? C17 C18 C1 111.9(4) . . ? C17 C18 H18A 109.2 . . ? C1 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? C1 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 C20 H20A 109.5 . . ? C1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 C21 H21A 109.5 . . ? C10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 C22 H22A 109.5 . . ? C10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C8 C23 C10 114.1(4) . . ? C8 C23 H23A 108.7 . . ? C10 C23 H23A 108.7 . . ? C8 C23 H23B 108.7 . . ? C10 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C17 C24 C1 112.4(4) . . ? C17 C24 H24A 109.1 . . ? C1 C24 H24A 109.1 . . ? C17 C24 H24B 109.1 . . ? C1 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.382 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.105 #============================================================================== data_19f #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; cis-2,8-Difluoro-4b,5,6,10b,11,12-hexahydrochrysene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 F2' _chemical_formula_sum 'C18 H16 F2' _chemical_formula_weight 270.31 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/C ' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.4310(10) _cell_length_b 7.5500(3) _cell_length_c 14.3850(11) _cell_angle_alpha 90.00 _cell_angle_beta 116.144(3) _cell_angle_gamma 90.00 _cell_volume 1309.46(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _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 'Mac Science DIP2000' _diffrn_measurement_method IP _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2751 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.15 _reflns_number_total 2751 _reflns_number_gt 2085 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.1148P)^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 SHELXL _refine_ls_extinction_coef 0.027(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2751 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 F20 F 0.70984(8) 0.16211(12) 0.77905(7) 0.0291(3) Uani 1 1 d . . . C4 C -0.09815(13) 0.24780(19) 0.54167(12) 0.0227(4) Uani 1 1 d . . . H4 H -0.1418 0.3018 0.4766 0.027 Uiso 1 1 calc R . . F19 F -0.25673(8) 0.22914(14) 0.57167(7) 0.0352(3) Uani 1 1 d . . . C3 C -0.14598(13) 0.1984(2) 0.60492(12) 0.0236(4) Uani 1 1 d . . . C1 C 0.02529(14) 0.0908(2) 0.73168(12) 0.0249(4) Uani 1 1 d . . . H1 H 0.0678 0.0375 0.7972 0.030 Uiso 1 1 calc R . . C15 C 0.36989(13) 0.12726(19) 0.67281(12) 0.0214(4) Uani 1 1 d . . . C10 C 0.41830(14) 0.1197(2) 0.60404(12) 0.0246(4) Uani 1 1 d . . . H10 H 0.3717 0.1071 0.5320 0.030 Uiso 1 1 calc R . . C6 C 0.07842(14) 0.13827(19) 0.67035(12) 0.0223(4) Uani 1 1 d . . . C9 C 0.24428(13) 0.12374(19) 0.62842(12) 0.0217(4) Uani 1 1 d . . . H9 H 0.2182 0.0188 0.5813 0.026 Uiso 1 1 calc R . . C13 C 0.55397(14) 0.1510(2) 0.81405(12) 0.0234(4) Uani 1 1 d . . . H13 H 0.6017 0.1595 0.8860 0.028 Uiso 1 1 calc R . . C8 C 0.19195(13) 0.2884(2) 0.56183(12) 0.0233(4) Uani 1 1 d . . . H8A H 0.2094 0.3943 0.6069 0.028 Uiso 1 1 calc R . . H8B H 0.2238 0.3061 0.5122 0.028 Uiso 1 1 calc R . . C18 C 0.20168(14) 0.0997(2) 0.71076(12) 0.0275(4) Uani 1 1 d . . . H18 H 0.2129 -0.0276 0.7320 0.033 Uiso 1 1 calc R . . C5 C 0.01511(13) 0.21801(18) 0.57385(11) 0.0203(3) Uani 1 1 d . . . C2 C -0.08695(14) 0.1189(2) 0.70007(12) 0.0249(4) Uani 1 1 d . . . H2 H -0.1219 0.0849 0.7422 0.030 Uiso 1 1 calc R . . C12 C 0.59731(13) 0.14771(19) 0.74360(13) 0.0232(4) Uani 1 1 d . . . C17 C 0.27107(14) 0.2092(2) 0.80733(13) 0.0307(4) Uani 1 1 d . . . H17A H 0.2398 0.1983 0.8578 0.037 Uiso 1 1 calc R . . H17B H 0.2686 0.3356 0.7882 0.037 Uiso 1 1 calc R . . C7 C 0.06682(13) 0.2672(2) 0.50287(11) 0.0218(4) Uani 1 1 d . . . H7A H 0.0340 0.3797 0.4671 0.026 Uiso 1 1 calc R . . H7B H 0.0497 0.1742 0.4495 0.026 Uiso 1 1 calc R . . C14 C 0.43940(14) 0.14167(19) 0.77909(12) 0.0219(4) Uani 1 1 d . . . C11 C 0.53248(14) 0.1302(2) 0.63838(13) 0.0252(4) Uani 1 1 d . . . H11 H 0.5646 0.1256 0.5913 0.030 Uiso 1 1 calc R . . C16 C 0.39177(14) 0.1444(2) 0.85692(12) 0.0274(4) Uani 1 1 d . . . H16A H 0.4371 0.2234 0.9152 0.033 Uiso 1 1 calc R . . H16B H 0.3951 0.0237 0.8850 0.033 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 F20 0.0210(5) 0.0336(6) 0.0321(6) 0.0042(4) 0.0111(4) 0.0010(4) C4 0.0224(8) 0.0238(8) 0.0183(8) -0.0014(6) 0.0056(6) -0.0022(6) F19 0.0196(5) 0.0527(7) 0.0319(6) 0.0030(4) 0.0099(4) -0.0006(4) C3 0.0178(8) 0.0262(8) 0.0252(8) -0.0040(6) 0.0078(7) -0.0025(6) C1 0.0273(9) 0.0264(8) 0.0221(8) 0.0042(6) 0.0121(7) 0.0008(6) C15 0.0245(9) 0.0210(8) 0.0193(8) -0.0003(5) 0.0102(7) 0.0001(6) C10 0.0256(9) 0.0287(8) 0.0195(8) -0.0004(6) 0.0099(7) -0.0006(6) C6 0.0242(9) 0.0218(8) 0.0209(8) 0.0010(5) 0.0099(7) -0.0001(6) C9 0.0234(9) 0.0231(8) 0.0182(8) -0.0007(5) 0.0088(7) -0.0010(6) C13 0.0235(9) 0.0240(8) 0.0200(8) 0.0002(6) 0.0071(7) 0.0022(6) C8 0.0253(9) 0.0254(8) 0.0200(8) 0.0023(6) 0.0106(7) -0.0007(6) C18 0.0267(9) 0.0351(9) 0.0218(8) 0.0039(6) 0.0117(7) 0.0024(7) C5 0.0240(8) 0.0181(7) 0.0177(7) -0.0018(5) 0.0082(6) -0.0015(5) C2 0.0284(9) 0.0239(8) 0.0257(8) 0.0004(6) 0.0150(7) -0.0033(6) C12 0.0190(8) 0.0213(8) 0.0281(9) 0.0030(6) 0.0094(7) 0.0016(5) C17 0.0308(10) 0.0410(10) 0.0223(9) -0.0011(7) 0.0135(8) 0.0021(7) C7 0.0253(9) 0.0221(8) 0.0170(8) 0.0003(5) 0.0083(7) -0.0012(6) C14 0.0242(9) 0.0216(7) 0.0193(8) 0.0011(5) 0.0091(7) 0.0025(6) C11 0.0278(9) 0.0269(8) 0.0251(9) 0.0007(6) 0.0156(7) -0.0003(6) C16 0.0260(9) 0.0384(9) 0.0167(8) -0.0018(6) 0.0083(7) 0.0022(6) _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 F20 C12 1.3700(18) . ? C4 C3 1.377(2) . ? C4 C5 1.399(2) . ? C4 H4 0.9500 . ? F19 C3 1.3669(18) . ? C3 C2 1.380(2) . ? C1 C2 1.386(2) . ? C1 C6 1.404(2) . ? C1 H1 0.9500 . ? C15 C14 1.401(2) . ? C15 C10 1.404(2) . ? C15 C9 1.518(2) . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C6 C5 1.404(2) . ? C6 C18 1.522(2) . ? C9 C18 1.536(2) . ? C9 C8 1.537(2) . ? C9 H9 1.0000 . ? C13 C12 1.373(2) . ? C13 C14 1.394(2) . ? C13 H13 0.9500 . ? C8 C7 1.521(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C18 C17 1.530(2) . ? C18 H18 1.0000 . ? C5 C7 1.513(2) . ? C2 H2 0.9500 . ? C12 C11 1.380(2) . ? C17 C16 1.535(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C14 C16 1.515(2) . ? C11 H11 0.9500 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 C3 C4 C5 119.58(14) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? F19 C3 C4 118.38(14) . . ? F19 C3 C2 118.81(14) . . ? C4 C3 C2 122.81(15) . . ? C2 C1 C6 122.37(15) . . ? C2 C1 H1 118.8 . . ? C6 C1 H1 118.8 . . ? C14 C15 C10 118.64(15) . . ? C14 C15 C9 122.89(14) . . ? C10 C15 C9 118.46(13) . . ? C11 C10 C15 121.86(14) . . ? C11 C10 H10 119.1 . . ? C15 C10 H10 119.1 . . ? C1 C6 C5 118.46(15) . . ? C1 C6 C18 118.67(14) . . ? C5 C6 C18 122.86(14) . . ? C15 C9 C18 113.58(13) . . ? C15 C9 C8 111.48(12) . . ? C18 C9 C8 110.63(13) . . ? C15 C9 H9 106.9 . . ? C18 C9 H9 106.9 . . ? C8 C9 H9 106.9 . . ? C12 C13 C14 119.49(14) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C7 C8 C9 110.61(12) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C6 C18 C17 111.62(13) . . ? C6 C18 C9 113.26(13) . . ? C17 C18 C9 110.58(14) . . ? C6 C18 H18 107.0 . . ? C17 C18 H18 107.0 . . ? C9 C18 H18 107.0 . . ? C4 C5 C6 119.50(14) . . ? C4 C5 C7 119.52(13) . . ? C6 C5 C7 120.96(14) . . ? C3 C2 C1 117.28(15) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? F20 C12 C13 118.72(14) . . ? F20 C12 C11 118.38(14) . . ? C13 C12 C11 122.90(15) . . ? C18 C17 C16 110.23(14) . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C5 C7 C8 111.87(12) . . ? C5 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C5 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C13 C14 C15 119.75(15) . . ? C13 C14 C16 119.42(14) . . ? C15 C14 C16 120.82(15) . . ? C12 C11 C10 117.33(15) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C14 C16 C17 111.36(13) . . ? C14 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C14 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.699 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.064 #============================================================================== data_20 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; cis-7-Fluoro-3-[4-fluoro-2-(1-methoxy-1-methylethyl)phenyl]-1,1,4-trimethyl- 1,2,3,4-tetrahydronapthalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 F2 O' _chemical_formula_sum 'C23 H28 F2 O' _chemical_formula_weight 358.45 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/C ' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.5450(5) _cell_length_b 7.8080(3) _cell_length_c 20.6670(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.287(2) _cell_angle_gamma 90.00 _cell_volume 1959.69(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4290 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.07 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9627 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mac Science DIP2000' _diffrn_measurement_method ' phi scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4290 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 27.07 _reflns_number_total 4290 _reflns_number_gt 3165 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.1090P)^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 SHELXL _refine_ls_extinction_coef 0.029(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4290 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.29973(13) 0.1326(2) 0.83813(8) 0.0213(3) Uani 1 1 d . . . H1 H 0.2795 0.2550 0.8244 0.026 Uiso 1 1 calc R . . C2 C 0.25964(12) 0.02868(19) 0.76705(8) 0.0203(3) Uani 1 1 d . . . H2 H 0.2942 0.0816 0.7380 0.024 Uiso 1 1 calc R . . C3 C 0.30540(13) -0.1546(2) 0.78585(9) 0.0221(3) Uani 1 1 d . . . H3A H 0.2830 -0.2037 0.8215 0.027 Uiso 1 1 calc R . . H3B H 0.2726 -0.2261 0.7418 0.027 Uiso 1 1 calc R . . C4 C 0.43163(13) -0.16171(19) 0.81689(8) 0.0206(3) Uani 1 1 d . . . C5 C 0.48555(13) -0.00992(19) 0.86690(8) 0.0197(3) Uani 1 1 d . . . C6 C 0.60118(13) -0.0036(2) 0.90365(8) 0.0214(3) Uani 1 1 d . . . H6 H 0.6440 -0.0930 0.8977 0.026 Uiso 1 1 calc R . . C7 C 0.65179(13) 0.1320(2) 0.94813(9) 0.0231(3) Uani 1 1 d . . . C8 C 0.59496(13) 0.2636(2) 0.96132(9) 0.0246(4) Uani 1 1 d . . . H8 H 0.6322 0.3544 0.9935 0.030 Uiso 1 1 calc R . . C9 C 0.48082(14) 0.2566(2) 0.92524(9) 0.0238(3) Uani 1 1 d . . . H9 H 0.4393 0.3449 0.9333 0.029 Uiso 1 1 calc R . . C10 C 0.42473(13) 0.12401(19) 0.87736(8) 0.0199(3) Uani 1 1 d . . . C11 C 0.24920(14) 0.0816(2) 0.88888(9) 0.0273(4) Uani 1 1 d . . . H11A H 0.2637 -0.0399 0.9014 0.041 Uiso 1 1 calc R . . H11B H 0.1695 0.1012 0.8647 0.041 Uiso 1 1 calc R . . H11C H 0.2821 0.1509 0.9329 0.041 Uiso 1 1 calc R . . C12 C 0.47049(14) -0.3304(2) 0.85903(9) 0.0255(4) Uani 1 1 d . . . H12A H 0.5500 -0.3431 0.8757 0.038 Uiso 1 1 calc R . . H12B H 0.4321 -0.4267 0.8275 0.038 Uiso 1 1 calc R . . H12C H 0.4541 -0.3288 0.9007 0.038 Uiso 1 1 calc R . . C13 C 0.46482(14) -0.1599(2) 0.75434(9) 0.0252(4) Uani 1 1 d . . . H13A H 0.4383 -0.0541 0.7264 0.038 Uiso 1 1 calc R . . H13B H 0.4320 -0.2588 0.7229 0.038 Uiso 1 1 calc R . . H13C H 0.5452 -0.1656 0.7740 0.038 Uiso 1 1 calc R . . C14 C 0.08065(13) 0.1322(2) 0.65748(9) 0.0229(3) Uani 1 1 d . . . C15 C 0.13548(13) 0.0323(2) 0.72053(9) 0.0211(3) Uani 1 1 d . . . C16 C 0.07072(13) -0.0728(2) 0.74190(9) 0.0230(3) Uani 1 1 d . . . H16 H 0.1069 -0.1437 0.7831 0.028 Uiso 1 1 calc R . . C17 C -0.04326(13) -0.0778(2) 0.70577(9) 0.0249(4) Uani 1 1 d . . . H17 H -0.0849 -0.1497 0.7215 0.030 Uiso 1 1 calc R . . C18 C -0.09325(13) 0.0251(2) 0.64646(9) 0.0249(4) Uani 1 1 d . . . C19 C -0.03489(14) 0.1278(2) 0.62134(9) 0.0251(4) Uani 1 1 d . . . H19 H -0.0730 0.1958 0.5794 0.030 Uiso 1 1 calc R . . C20 C 0.14109(14) 0.2504(2) 0.62592(9) 0.0300(4) Uani 1 1 d . . . C21 C 0.19032(15) 0.4114(2) 0.67385(10) 0.0310(4) Uani 1 1 d . . . H21A H 0.2467 0.3759 0.7214 0.047 Uiso 1 1 calc R . . H21B H 0.1317 0.4734 0.6795 0.047 Uiso 1 1 calc R . . H21C H 0.2235 0.4864 0.6508 0.047 Uiso 1 1 calc R . . C22 C 0.06610(15) 0.3099(3) 0.54854(11) 0.0391(5) Uani 1 1 d . . . H22A H 0.1105 0.3677 0.5284 0.059 Uiso 1 1 calc R . . H22B H 0.0107 0.3895 0.5493 0.059 Uiso 1 1 calc R . . H22C H 0.0293 0.2104 0.5186 0.059 Uiso 1 1 calc R . . C23 C 0.20913(16) 0.0145(2) 0.58341(10) 0.0329(4) Uani 1 1 d . . . H23A H 0.1606 -0.0579 0.5956 0.049 Uiso 1 1 calc R . . H23B H 0.2772 -0.0479 0.5934 0.049 Uiso 1 1 calc R . . H23C H 0.1719 0.0446 0.5321 0.049 Uiso 1 1 calc R . . F24 F 0.76482(8) 0.13684(13) 0.98151(5) 0.0287(3) Uani 1 1 d . . . F25 F -0.20570(8) 0.02682(14) 0.60987(6) 0.0347(3) Uani 1 1 d . . . O26 O 0.23471(10) 0.16574(15) 0.62551(6) 0.0289(3) 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 0.0182(8) 0.0210(7) 0.0230(8) 0.0035(6) 0.0075(7) 0.0030(6) C2 0.0165(8) 0.0214(7) 0.0218(8) 0.0035(6) 0.0075(6) 0.0001(6) C3 0.0196(8) 0.0211(8) 0.0253(8) 0.0007(6) 0.0096(7) 0.0002(6) C4 0.0187(8) 0.0207(7) 0.0219(8) 0.0016(6) 0.0085(7) 0.0031(6) C5 0.0191(8) 0.0214(7) 0.0180(7) 0.0027(6) 0.0076(6) 0.0000(6) C6 0.0197(8) 0.0239(8) 0.0209(8) 0.0027(6) 0.0094(7) 0.0038(6) C7 0.0137(7) 0.0317(8) 0.0210(8) 0.0050(6) 0.0050(6) -0.0005(6) C8 0.0229(8) 0.0246(8) 0.0235(8) -0.0003(6) 0.0078(7) -0.0018(6) C9 0.0234(8) 0.0226(8) 0.0252(8) 0.0014(6) 0.0104(7) 0.0015(6) C10 0.0197(8) 0.0199(7) 0.0205(7) 0.0049(6) 0.0091(6) 0.0027(6) C11 0.0232(9) 0.0351(9) 0.0253(8) 0.0011(7) 0.0122(7) 0.0024(7) C12 0.0249(8) 0.0212(8) 0.0298(9) 0.0020(6) 0.0115(7) 0.0028(6) C13 0.0227(8) 0.0290(8) 0.0244(8) -0.0033(6) 0.0109(7) 0.0000(6) C14 0.0191(8) 0.0247(8) 0.0241(8) 0.0038(6) 0.0089(7) -0.0017(6) C15 0.0178(8) 0.0217(7) 0.0229(8) 0.0016(6) 0.0081(7) -0.0001(6) C16 0.0214(8) 0.0221(8) 0.0249(8) 0.0036(6) 0.0097(7) -0.0008(6) C17 0.0205(8) 0.0264(8) 0.0291(9) -0.0012(6) 0.0122(7) -0.0049(6) C18 0.0136(8) 0.0290(8) 0.0292(9) -0.0027(7) 0.0067(7) -0.0016(6) C19 0.0189(8) 0.0282(8) 0.0249(8) 0.0054(6) 0.0065(7) 0.0006(6) C20 0.0208(8) 0.0355(9) 0.0320(9) 0.0109(7) 0.0102(7) 0.0003(7) C21 0.0328(10) 0.0261(8) 0.0398(10) 0.0023(7) 0.0212(8) 0.0027(7) C22 0.0263(9) 0.0515(12) 0.0341(10) 0.0205(9) 0.0084(8) 0.0001(8) C23 0.0347(10) 0.0361(10) 0.0296(9) -0.0075(7) 0.0158(8) -0.0049(8) F24 0.0161(5) 0.0375(6) 0.0285(5) -0.0008(4) 0.0062(4) -0.0023(4) F25 0.0139(5) 0.0443(6) 0.0394(6) 0.0062(5) 0.0058(5) -0.0027(4) O26 0.0256(6) 0.0334(7) 0.0291(6) -0.0004(5) 0.0133(5) -0.0004(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 C10 1.521(2) . ? C1 C11 1.537(2) . ? C1 C2 1.551(2) . ? C1 H1 1.0000 . ? C2 C15 1.524(2) . ? C2 C3 1.539(2) . ? C2 H2 1.0000 . ? C3 C4 1.538(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(2) . ? C4 C12 1.538(2) . ? C4 C13 1.545(2) . ? C5 C10 1.406(2) . ? C5 C6 1.407(2) . ? C6 C7 1.370(2) . ? C6 H6 0.9500 . ? C7 F24 1.3732(17) . ? C7 C8 1.382(2) . ? C8 C9 1.389(2) . ? C8 H8 0.9500 . ? C9 C10 1.401(2) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.405(2) . ? C14 C15 1.415(2) . ? C14 C20 1.556(2) . ? C15 C16 1.407(2) . ? C16 C17 1.386(2) . ? C16 H16 0.9500 . ? C17 C18 1.368(2) . ? C17 H17 0.9500 . ? C18 F25 1.3681(18) . ? C18 C19 1.379(2) . ? C19 H19 0.9500 . ? C20 O26 1.433(2) . ? C20 C22 1.538(2) . ? C20 C21 1.556(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O26 1.416(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 C10 C1 C11 110.60(13) . . ? C10 C1 C2 108.78(12) . . ? C11 C1 C2 115.84(13) . . ? C10 C1 H1 107.1 . . ? C11 C1 H1 107.1 . . ? C2 C1 H1 107.1 . . ? C15 C2 C3 112.63(12) . . ? C15 C2 C1 114.44(12) . . ? C3 C2 C1 108.32(12) . . ? C15 C2 H2 107.0 . . ? C3 C2 H2 107.0 . . ? C1 C2 H2 107.0 . . ? C4 C3 C2 112.82(12) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C12 109.86(13) . . ? C5 C4 C3 111.34(12) . . ? C12 C4 C3 107.80(12) . . ? C5 C4 C13 109.24(12) . . ? C12 C4 C13 109.16(12) . . ? C3 C4 C13 109.41(13) . . ? C10 C5 C6 118.63(14) . . ? C10 C5 C4 122.92(14) . . ? C6 C5 C4 118.45(13) . . ? C7 C6 C5 119.72(14) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 F24 118.27(14) . . ? C6 C7 C8 123.37(15) . . ? F24 C7 C8 118.36(14) . . ? C7 C8 C9 116.74(15) . . ? C7 C8 H8 121.6 . . ? C9 C8 H8 121.6 . . ? C8 C9 C10 122.34(14) . . ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C9 C10 C5 119.13(14) . . ? C9 C10 C1 118.13(13) . . ? C5 C10 C1 122.73(14) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.89(14) . . ? C19 C14 C20 117.44(14) . . ? C15 C14 C20 123.66(14) . . ? C16 C15 C14 117.68(14) . . ? C16 C15 C2 117.30(14) . . ? C14 C15 C2 125.02(13) . . ? C17 C16 C15 123.23(15) . . ? C17 C16 H16 118.4 . . ? C15 C16 H16 118.4 . . ? C18 C17 C16 117.21(14) . . ? C18 C17 H17 121.4 . . ? C16 C17 H17 121.4 . . ? C17 C18 F25 119.30(14) . . ? C17 C18 C19 122.69(15) . . ? F25 C18 C19 118.01(15) . . ? C18 C19 C14 120.24(15) . . ? C18 C19 H19 119.9 . . ? C14 C19 H19 119.9 . . ? O26 C20 C22 108.16(14) . . ? O26 C20 C14 111.11(13) . . ? C22 C20 C14 112.78(14) . . ? O26 C20 C21 104.22(13) . . ? C22 C20 C21 108.49(15) . . ? C14 C20 C21 111.67(14) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O26 C23 H23A 109.5 . . ? O26 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O26 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C23 O26 C20 114.32(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.199 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.061 #============================================================================== data_21a #============================================================================== # CHEMICAL DATA _chemical_name_systematic cis-1,1,4-Trimethyl-3-phenyl-1,2,3,4-tetrahydronaphthalene _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22' _chemical_formula_sum 'C19 H22' _chemical_formula_weight 250.37 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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 8.4780(8) _cell_length_b 9.8980(10) _cell_length_c 17.1870(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.297(5) _cell_angle_gamma 90.00 _cell_volume 1441.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3010 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus rotating anode' _diffrn_source_type 'Mac Science MXC18KHF22' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mac Science DIP2000' _diffrn_measurement_method ' phi scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3010 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.14 _reflns_number_total 3010 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DIP2000 software Xpress (MAC Science, 1989) ; _computing_cell_refinement ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_reduction ; DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SIR97 (Altomare, et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus (Mackay et al., 1999)' _computing_publication_material 'maXus (Mackay et al., 1999)' _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^)+(0.0891P)^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 SHELXL _refine_ls_extinction_coef 0.110(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3010 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.88805(17) 0.23588(15) 0.59780(7) 0.0218(3) Uani 1 1 d . . . C2 C 0.78922(17) 0.25819(15) 0.67096(7) 0.0220(3) Uani 1 1 d . . . H2A H 0.8182 0.3461 0.6947 0.026 Uiso 1 1 calc R . . H2B H 0.6761 0.2620 0.6555 0.026 Uiso 1 1 calc R . . C3 C 0.81443(17) 0.14589(15) 0.73138(7) 0.0213(3) Uani 1 1 d . . . H3 H 0.8041 0.0581 0.7029 0.026 Uiso 1 1 calc R . . C4 C 0.98549(17) 0.15332(15) 0.76359(7) 0.0220(3) Uani 1 1 d . . . H4 H 1.0061 0.0678 0.7931 0.026 Uiso 1 1 calc R . . C5 C 1.10178(17) 0.15734(14) 0.69701(7) 0.0205(3) Uani 1 1 d . . . C6 C 1.25845(17) 0.12048(15) 0.71288(8) 0.0231(3) Uani 1 1 d . . . H6 H 1.2891 0.0968 0.7646 0.028 Uiso 1 1 calc R . . C7 C 1.37007(18) 0.11755(15) 0.65539(8) 0.0244(3) Uani 1 1 d . . . H7 H 1.4757 0.0916 0.6675 0.029 Uiso 1 1 calc R . . C8 C 1.32589(18) 0.15300(15) 0.57995(8) 0.0255(3) Uani 1 1 d . . . H8 H 1.4010 0.1505 0.5398 0.031 Uiso 1 1 calc R . . C9 C 1.17253(17) 0.19183(15) 0.56341(7) 0.0241(3) Uani 1 1 d . . . H9 H 1.1441 0.2168 0.5116 0.029 Uiso 1 1 calc R . . C10 C 1.05685(17) 0.19568(14) 0.62075(7) 0.0207(3) Uani 1 1 d . . . C11 C 0.88504(19) 0.36801(16) 0.55105(8) 0.0272(4) Uani 1 1 d . . . H11A H 0.9394 0.4390 0.5810 0.041 Uiso 1 1 calc R . . H11B H 0.7754 0.3951 0.5406 0.041 Uiso 1 1 calc R . . H11C H 0.9384 0.3544 0.5017 0.041 Uiso 1 1 calc R . . C12 C 0.81350(18) 0.12336(16) 0.54700(8) 0.0272(4) Uani 1 1 d . . . H12A H 0.8759 0.1109 0.5002 0.041 Uiso 1 1 calc R . . H12B H 0.7054 0.1489 0.5319 0.041 Uiso 1 1 calc R . . H12C H 0.8118 0.0388 0.5766 0.041 Uiso 1 1 calc R . . C13 C 1.01535(19) 0.27114(16) 0.82063(8) 0.0275(4) Uani 1 1 d . . . H13A H 1.1257 0.2697 0.8388 0.041 Uiso 1 1 calc R . . H13B H 0.9462 0.2617 0.8652 0.041 Uiso 1 1 calc R . . H13C H 0.9931 0.3570 0.7941 0.041 Uiso 1 1 calc R . . C14 C 0.69311(17) 0.14378(15) 0.79544(7) 0.0213(3) Uani 1 1 d . . . C15 C 0.65558(17) 0.02132(15) 0.83100(7) 0.0235(3) Uani 1 1 d . . . H15 H 0.7069 -0.0592 0.8154 0.028 Uiso 1 1 calc R . . C16 C 0.54370(18) 0.01611(16) 0.88901(7) 0.0255(3) Uani 1 1 d . . . H16 H 0.5195 -0.0678 0.9128 0.031 Uiso 1 1 calc R . . C17 C 0.46725(18) 0.13290(16) 0.91232(8) 0.0259(3) Uani 1 1 d . . . H17 H 0.3903 0.1291 0.9516 0.031 Uiso 1 1 calc R . . C18 C 0.50435(19) 0.25524(16) 0.87772(8) 0.0272(4) Uani 1 1 d . . . H18 H 0.4533 0.3357 0.8937 0.033 Uiso 1 1 calc R . . C19 C 0.61635(18) 0.26033(15) 0.81959(7) 0.0258(3) Uani 1 1 d . . . H19 H 0.6406 0.3445 0.7961 0.031 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 0.0250(8) 0.0236(8) 0.0169(6) 0.0021(5) 0.0015(5) -0.0001(6) C2 0.0231(7) 0.0239(8) 0.0190(7) 0.0014(5) 0.0012(5) -0.0003(6) C3 0.0260(8) 0.0223(8) 0.0158(6) 0.0000(5) 0.0029(5) -0.0006(6) C4 0.0273(8) 0.0224(8) 0.0164(6) 0.0023(5) 0.0002(5) 0.0000(6) C5 0.0253(8) 0.0185(7) 0.0179(6) -0.0003(5) 0.0015(5) -0.0023(6) C6 0.0253(8) 0.0220(8) 0.0219(7) 0.0012(5) -0.0030(5) -0.0017(6) C7 0.0211(7) 0.0233(8) 0.0288(7) -0.0002(5) -0.0013(5) -0.0014(6) C8 0.0256(8) 0.0272(8) 0.0239(7) -0.0010(5) 0.0058(5) -0.0029(6) C9 0.0255(8) 0.0273(8) 0.0196(6) 0.0015(5) 0.0010(5) -0.0026(6) C10 0.0247(8) 0.0179(7) 0.0194(6) -0.0010(5) 0.0002(5) -0.0028(6) C11 0.0309(8) 0.0297(9) 0.0211(7) 0.0049(5) 0.0037(6) 0.0030(6) C12 0.0277(8) 0.0342(9) 0.0195(7) -0.0017(5) -0.0002(5) -0.0027(7) C13 0.0309(8) 0.0322(9) 0.0194(7) -0.0025(5) 0.0000(5) -0.0023(7) C14 0.0256(8) 0.0245(8) 0.0137(6) -0.0001(5) 0.0000(5) -0.0020(6) C15 0.0258(8) 0.0244(8) 0.0202(6) 0.0009(5) 0.0007(5) -0.0013(6) C16 0.0286(8) 0.0278(9) 0.0202(7) 0.0045(5) 0.0010(5) -0.0040(6) C17 0.0277(8) 0.0326(9) 0.0174(6) 0.0002(5) 0.0026(5) -0.0041(6) C18 0.0329(9) 0.0269(9) 0.0219(7) -0.0036(5) 0.0049(6) 0.0004(7) C19 0.0333(9) 0.0224(8) 0.0219(7) 0.0017(5) 0.0046(6) -0.0021(6) _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 C10 1.5285(19) . ? C1 C11 1.5349(19) . ? C1 C12 1.542(2) . ? C1 C2 1.5425(18) . ? C2 C3 1.5328(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C14 1.5237(18) . ? C3 C4 1.5424(19) . ? C3 H3 1.0000 . ? C4 C5 1.5278(18) . ? C4 C13 1.541(2) . ? C4 H4 1.0000 . ? C5 C6 1.398(2) . ? C5 C10 1.4088(18) . ? C6 C7 1.384(2) . ? C6 H6 0.9500 . ? C7 C8 1.387(2) . ? C7 H7 0.9500 . ? C8 C9 1.379(2) . ? C8 H8 0.9500 . ? C9 C10 1.4065(18) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.392(2) . ? C14 C15 1.397(2) . ? C15 C16 1.3926(19) . ? C15 H15 0.9500 . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C18 C19 1.395(2) . ? C18 H18 0.9500 . ? C19 H19 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 C10 C1 C11 111.18(12) . . ? C10 C1 C12 109.12(12) . . ? C11 C1 C12 108.50(11) . . ? C10 C1 C2 110.47(10) . . ? C11 C1 C2 107.57(11) . . ? C12 C1 C2 109.98(12) . . ? C3 C2 C1 112.24(11) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C14 C3 C2 114.42(12) . . ? C14 C3 C4 112.70(10) . . ? C2 C3 C4 108.92(11) . . ? C14 C3 H3 106.8 . . ? C2 C3 H3 106.8 . . ? C4 C3 H3 106.8 . . ? C5 C4 C13 110.93(12) . . ? C5 C4 C3 110.48(10) . . ? C13 C4 C3 113.83(12) . . ? C5 C4 H4 107.1 . . ? C13 C4 H4 107.1 . . ? C3 C4 H4 107.1 . . ? C6 C5 C10 119.17(13) . . ? C6 C5 C4 118.26(11) . . ? C10 C5 C4 122.58(12) . . ? C7 C6 C5 121.88(12) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 119.20(13) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 119.78(13) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 122.15(12) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C9 C10 C5 117.81(13) . . ? C9 C10 C1 119.33(11) . . ? C5 C10 C1 122.82(12) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.40(13) . . ? C19 C14 C3 122.12(13) . . ? C15 C14 C3 119.47(13) . . ? C16 C15 C14 120.72(14) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.37(14) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.39(13) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.18(14) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C14 C19 C18 120.93(14) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.360 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.061