# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 145452, 145453, 100797 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Cross, Wendy' 'Hawkes, G.' 'Kroemer, Romano T.' 'Liedl, Klaus R.' 'Loerting, Thomas' 'Nasser, Rima' 'Pritchard, R.' 'Steele, Melanie' 'Watkinson, Michael' 'Whiting, Andrew' _publ_contact_author_name 'Dr Andrew Whiting' _publ_contact_author_address ; Dr Andrew Whiting Chemistry Department UMIST PO Box 88 Manchester M60 1QD UK ; _publ_contact_author_email 'a.whiting@umist.ac.uk' data_s/gd1063 _database_code_CSD 145452 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 O2' _chemical_formula_weight 506.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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' 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 14.053(3) _cell_length_b 13.639(4) _cell_length_c 15.490(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.00(2) _cell_angle_gamma 90.00 _cell_volume 2961.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.3 _cell_measurement_theta_max 25.1 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8381 _exptl_absorpt_correction_T_max 0.9257 _exptl_absorpt_process_details 'Texsan/Process MSC (1985)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Scintillarion counter' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 150 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 5035 _diffrn_reflns_av_R_equivalents 0.0969 _diffrn_reflns_av_sigmaI/netI 0.1057 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 65.09 _reflns_number_total 4819 _reflns_number_gt 2369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'AFC-CTR (Molecular Structure Corporation, 1985' _computing_cell_refinement 'AFC-CTR (Molecular Structure Corporation, 1985' _computing_data_reduction 'TEXSAN-PROCESS (Molecular Structure Corporation, 1985)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Farrugia, 1997; Burnett and Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.7512P] 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 SHELXL _refine_ls_extinction_coef 0.00187(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4819 _refine_ls_number_parameters 512 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.010 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.71834(12) 0.12975(12) 0.56531(11) 0.0594(5) Uani 1 d . . . O2 O 0.80263(12) 0.36449(13) 0.80080(9) 0.0598(5) Uani 1 d . . . C1 C 0.80193(14) 0.61291(15) 0.50954(13) 0.0356(5) Uani 1 d . . . C2 C 0.84606(16) 0.70304(17) 0.51922(15) 0.0462(7) Uani 1 d . . . C3 C 0.84069(17) 0.77590(18) 0.45511(17) 0.0534(7) Uani 1 d . . . C4 C 0.78881(16) 0.75860(17) 0.37952(15) 0.0476(6) Uani 1 d . . . C4A C 0.74597(15) 0.66639(16) 0.36689(13) 0.0395(6) Uani 1 d . . . C5 C 0.69439(16) 0.66102(18) 0.28594(15) 0.0503(7) Uani 1 d . . . C6 C 0.64918(18) 0.5769(2) 0.26336(16) 0.0601(8) Uani 1 d . . . C7 C 0.65530(18) 0.49677(19) 0.32128(15) 0.0524(7) Uani 1 d . . . C8 C 0.70514(14) 0.49977(16) 0.40129(13) 0.0368(6) Uani 1 d . . . C8A C 0.75091(14) 0.58951(15) 0.42834(13) 0.0347(5) Uani 1 d . . . C9 C 0.7663(2) 0.8216(2) 0.30064(19) 0.0705(9) Uani 1 d . . . C10 C 0.7021(2) 0.7578(2) 0.23938(18) 0.0689(9) Uani 1 d . . . C11 C 0.70987(14) 0.40575(15) 0.45037(12) 0.0339(5) Uani 1 d . . . C12 C 0.62685(15) 0.35614(16) 0.46689(14) 0.0384(6) Uani 1 d . . . C13 C 0.62538(15) 0.26434(15) 0.50519(13) 0.0364(6) Uani 1 d . . . C14 C 0.71447(15) 0.22160(15) 0.52684(13) 0.0389(6) Uani 1 d . . . C15 C 0.80030(14) 0.27074(16) 0.51548(14) 0.0390(6) Uani 1 d . . . C16 C 0.79634(14) 0.36221(16) 0.47626(13) 0.0374(6) Uani 1 d . . . C17 C 0.53010(16) 0.21273(17) 0.51820(15) 0.0475(7) Uani 1 d . . . C18 C 0.5172(2) 0.1284(2) 0.4537(2) 0.0717(9) Uani 1 d . . . C19 C 0.5244(2) 0.1742(3) 0.61123(18) 0.0773(10) Uani 1 d . . . C20 C 0.44501(18) 0.2815(2) 0.5003(2) 0.0742(10) Uani 1 d . . . C21 C 0.7539(2) 0.0519(2) 0.5134(2) 0.0798(10) Uani 1 d . . . C22 C 0.89598(18) 0.2278(2) 0.54340(18) 0.0596(8) Uani 1 d . . . C23 C 0.80265(14) 0.54821(15) 0.58712(13) 0.0341(5) Uani 1 d . . . C24 C 0.88724(15) 0.52323(16) 0.63275(13) 0.0373(6) Uani 1 d . . . C25 C 0.89147(15) 0.46322(16) 0.70609(14) 0.0394(6) Uani 1 d . . . C26 C 0.80352(16) 0.42744(16) 0.73026(13) 0.0400(6) Uani 1 d . . . C27 C 0.71683(15) 0.45768(16) 0.69015(13) 0.0393(6) Uani 1 d . . . C28 C 0.71794(15) 0.51722(16) 0.61845(13) 0.0366(6) Uani 1 d . . . C29 C 0.98608(17) 0.44395(19) 0.75847(16) 0.0534(7) Uani 1 d . . . C30 C 1.0695(2) 0.4972(3) 0.7205(2) 0.0865(11) Uani 1 d . . . C31 C 0.9781(2) 0.4845(3) 0.85089(19) 0.0788(10) Uani 1 d . . . C32 C 1.0102(2) 0.3348(3) 0.7634(2) 0.0904(11) Uani 1 d . . . C33 C 0.7720(3) 0.2660(2) 0.7775(2) 0.0895(11) Uani 1 d . . . C34 C 0.62220(19) 0.4325(2) 0.72591(18) 0.0680(9) Uani 1 d . . . H2 H 0.8871(15) 0.7128(16) 0.5773(14) 0.055(7) Uiso 1 d . . . H3 H 0.8702(15) 0.8354(16) 0.4648(13) 0.047(6) Uiso 1 d . . . H7 H 0.6237(15) 0.4353(17) 0.3021(14) 0.054(7) Uiso 1 d . . . H8 H 0.6105(16) 0.5705(18) 0.2151(16) 0.065(7) Uiso 1 d . . . H9A H 0.827(2) 0.836(2) 0.279(2) 0.107(11) Uiso 1 d . . . H9B H 0.734(2) 0.884(2) 0.315(2) 0.112(11) Uiso 1 d . . . H10A H 0.6399(19) 0.789(2) 0.2267(18) 0.087(9) Uiso 1 d . . . H10B H 0.7324(17) 0.7461(19) 0.1806(17) 0.075(8) Uiso 1 d . . . H12 H 0.5694(13) 0.3883(14) 0.4465(12) 0.032(5) Uiso 1 d . . . H16 H 0.8561(13) 0.3960(14) 0.4706(12) 0.036(5) Uiso 1 d . . . H18A H 0.4561(18) 0.1000(19) 0.4636(17) 0.077(8) Uiso 1 d . . . H18B H 0.522(2) 0.157(3) 0.391(2) 0.138(13) Uiso 1 d . . . H18C H 0.568(2) 0.078(3) 0.471(2) 0.125(12) Uiso 1 d . . . H19A H 0.529(2) 0.234(2) 0.652(2) 0.116(12) Uiso 1 d . . . H19B H 0.456(2) 0.141(2) 0.6141(18) 0.092(9) Uiso 1 d . . . H19C H 0.574(3) 0.123(3) 0.630(2) 0.144(14) Uiso 1 d . . . H20A H 0.3847(18) 0.2421(19) 0.5071(17) 0.082(8) Uiso 1 d . . . H20B H 0.4459(19) 0.342(2) 0.5356(18) 0.091(10) Uiso 1 d . . . H20C H 0.445(2) 0.304(2) 0.437(2) 0.112(12) Uiso 1 d . . . H21A H 0.731(2) -0.003(3) 0.534(2) 0.123(13) Uiso 1 d . . . H21B H 0.823(3) 0.048(3) 0.536(3) 0.165(16) Uiso 1 d . . . H21C H 0.723(3) 0.051(4) 0.448(4) 0.22(2) Uiso 1 d . . . H22A H 0.8906(19) 0.192(2) 0.5932(18) 0.084(9) Uiso 1 d . . . H22C H 0.9440(19) 0.283(2) 0.5604(18) 0.091(9) Uiso 1 d . . . H22B H 0.9151(18) 0.183(2) 0.4994(17) 0.080(9) Uiso 1 d . . . H24 H 0.9457(14) 0.5507(15) 0.6183(13) 0.041(6) Uiso 1 d . . . H28 H 0.6563(13) 0.5377(14) 0.5869(12) 0.032(5) Uiso 1 d . . . H30A H 1.1266(19) 0.485(2) 0.7580(18) 0.083(9) Uiso 1 d . . . H30B H 1.076(2) 0.478(3) 0.665(2) 0.116(12) Uiso 1 d . . . H30C H 1.048(3) 0.571(3) 0.718(2) 0.143(14) Uiso 1 d . . . H31A H 1.042(2) 0.474(2) 0.883(2) 0.110(11) Uiso 1 d . . . H31B H 0.925(3) 0.442(3) 0.872(3) 0.158(16) Uiso 1 d . . . H31C H 0.969(2) 0.560(3) 0.853(2) 0.137(14) Uiso 1 d . . . H32A H 1.078(2) 0.328(2) 0.793(2) 0.103(10) Uiso 1 d . . . H32B H 0.956(3) 0.297(3) 0.803(2) 0.141(14) Uiso 1 d . . . H32C H 1.017(3) 0.312(3) 0.703(3) 0.140(14) Uiso 1 d . . . H33A H 0.830(3) 0.227(4) 0.808(3) 0.20(2) Uiso 1 d . . . H33B H 0.742(3) 0.240(3) 0.815(2) 0.131(14) Uiso 1 d . . . H33C H 0.737(3) 0.259(3) 0.724(3) 0.161(16) Uiso 1 d . . . H34A H 0.600(2) 0.375(3) 0.705(2) 0.115(12) Uiso 1 d . . . H34B H 0.569(3) 0.474(3) 0.698(3) 0.165(16) Uiso 1 d . . . H34C H 0.631(3) 0.435(3) 0.787(3) 0.161(16) Uiso 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 O1 0.0662(10) 0.0434(9) 0.0701(11) 0.0178(8) 0.0161(9) 0.0077(8) O2 0.0827(11) 0.0604(11) 0.0365(8) 0.0131(8) 0.0051(8) -0.0131(10) C1 0.0342(11) 0.0342(12) 0.0388(11) 0.0069(10) 0.0058(9) 0.0028(9) C2 0.0478(13) 0.0407(14) 0.0503(13) 0.0067(11) 0.0045(11) -0.0036(11) C3 0.0572(14) 0.0351(13) 0.0682(16) 0.0123(13) 0.0064(12) -0.0118(12) C4 0.0456(13) 0.0413(13) 0.0566(14) 0.0174(12) 0.0093(11) 0.0013(11) C4A 0.0368(11) 0.0426(13) 0.0397(12) 0.0112(10) 0.0081(10) 0.0044(10) C5 0.0483(13) 0.0549(15) 0.0480(13) 0.0227(12) 0.0048(11) -0.0017(12) C6 0.0618(16) 0.0748(18) 0.0416(13) 0.0170(13) -0.0108(12) -0.0065(14) C7 0.0588(15) 0.0515(15) 0.0458(13) 0.0052(12) -0.0041(12) -0.0066(13) C8 0.0368(11) 0.0380(12) 0.0362(11) 0.0047(10) 0.0077(9) 0.0004(10) C8A 0.0313(10) 0.0345(12) 0.0390(11) 0.0063(10) 0.0068(9) 0.0012(9) C9 0.0739(18) 0.0624(17) 0.0755(17) 0.0369(15) 0.0087(15) -0.0024(15) C10 0.0677(17) 0.0748(19) 0.0634(16) 0.0349(15) -0.0025(14) -0.0030(16) C11 0.0397(11) 0.0311(11) 0.0313(10) -0.0024(9) 0.0059(9) -0.0026(9) C12 0.0369(11) 0.0366(12) 0.0419(12) 0.0004(10) 0.0036(10) 0.0045(10) C13 0.0421(11) 0.0334(12) 0.0342(11) -0.0023(10) 0.0061(9) -0.0036(10) C14 0.0478(12) 0.0310(12) 0.0383(11) 0.0025(10) 0.0062(10) 0.0037(10) C15 0.0374(11) 0.0389(12) 0.0406(12) -0.0003(10) 0.0015(9) 0.0071(10) C16 0.0344(11) 0.0394(13) 0.0389(11) -0.0035(10) 0.0075(9) -0.0029(10) C17 0.0481(13) 0.0440(14) 0.0512(13) 0.0011(11) 0.0103(11) -0.0063(11) C18 0.0630(16) 0.0645(18) 0.088(2) -0.0157(16) 0.0117(15) -0.0169(16) C19 0.0739(18) 0.099(2) 0.0611(16) 0.0176(17) 0.0200(15) -0.0259(17) C20 0.0415(14) 0.0649(18) 0.119(2) 0.0088(18) 0.0225(15) -0.0040(14) C21 0.082(2) 0.0360(15) 0.121(3) -0.0027(17) 0.0080(19) 0.0132(15) C22 0.0488(14) 0.0586(17) 0.0705(17) 0.0029(15) -0.0017(13) 0.0084(13) C23 0.0383(11) 0.0310(11) 0.0336(11) -0.0026(9) 0.0065(9) 0.0009(10) C24 0.0374(11) 0.0383(13) 0.0369(11) 0.0015(10) 0.0077(9) -0.0007(10) C25 0.0439(12) 0.0370(13) 0.0375(11) -0.0019(10) 0.0033(10) 0.0070(10) C26 0.0549(13) 0.0370(12) 0.0288(10) 0.0013(10) 0.0082(10) -0.0022(11) C27 0.0455(12) 0.0411(13) 0.0324(11) -0.0021(10) 0.0115(9) -0.0062(11) C28 0.0396(12) 0.0361(12) 0.0345(11) -0.0040(10) 0.0053(9) 0.0023(10) C29 0.0529(14) 0.0606(16) 0.0462(13) 0.0078(13) 0.0000(11) 0.0104(13) C30 0.0375(14) 0.137(3) 0.083(2) 0.028(2) -0.0072(15) 0.0100(17) C31 0.0686(18) 0.111(3) 0.0544(16) -0.0129(17) -0.0149(14) -0.0041(18) C32 0.086(2) 0.087(2) 0.095(2) 0.009(2) -0.0199(19) 0.0376(18) C33 0.143(3) 0.0529(18) 0.0706(19) 0.0230(16) -0.008(2) -0.0370(19) C34 0.0567(15) 0.091(2) 0.0584(16) 0.0017(16) 0.0164(13) -0.0210(15) _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 O1 C14 1.387(3) . ? O1 C21 1.442(3) . ? O2 C26 1.390(3) . ? O2 C33 1.449(3) . ? C1 C2 1.380(3) . yes C1 C8A 1.440(3) . yes C1 C23 1.490(3) . yes C2 C3 1.403(3) . ? C3 C4 1.356(3) . ? C4 C4A 1.402(3) . yes C4 C9 1.509(3) . yes C4A C5 1.406(3) . yes C4A C8A 1.415(3) . yes C5 C6 1.346(4) . ? C5 C10 1.511(4) . yes C6 C7 1.412(4) . ? C7 C8 1.381(3) . yes C8 C8A 1.432(3) . yes C8 C11 1.490(3) . yes C9 C10 1.534(4) . yes C11 C16 1.386(3) . ? C11 C12 1.388(3) . ? C12 C13 1.386(3) . ? C13 C14 1.400(3) . ? C13 C17 1.538(3) . ? C14 C15 1.402(3) . ? C15 C16 1.387(3) . ? C15 C22 1.502(3) . ? C17 C18 1.526(4) . ? C17 C20 1.529(4) . ? C17 C19 1.541(4) . ? C23 C24 1.383(3) . ? C23 C28 1.383(3) . ? C24 C25 1.398(3) . ? C25 C26 1.404(3) . ? C25 C29 1.531(3) . ? C26 C27 1.391(3) . ? C27 C28 1.377(3) . ? C27 C34 1.515(3) . ? C29 C32 1.527(4) . ? C29 C30 1.531(4) . ? C29 C31 1.546(4) . ? 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 C14 O1 C21 115.5(2) . . ? C26 O2 C33 113.33(19) . . ? C2 C1 C8A 119.00(19) . . ? C2 C1 C23 117.53(19) . . yes C8A C1 C23 123.24(18) . . yes C1 C2 C3 123.5(2) . . ? C4 C3 C2 119.1(2) . . ? C3 C4 C4A 118.4(2) . . ? C3 C4 C9 132.1(2) . . ? C4A C4 C9 109.5(2) . . ? C4 C4A C5 111.2(2) . . yes C4 C4A C8A 124.8(2) . . ? C5 C4A C8A 124.0(2) . . ? C6 C5 C4A 118.7(2) . . ? C6 C5 C10 132.0(2) . . ? C4A C5 C10 109.3(2) . . ? C5 C6 C7 119.2(2) . . ? C8 C7 C6 123.5(2) . . ? C7 C8 C8A 118.5(2) . . ? C7 C8 C11 115.74(19) . . yes C8A C8 C11 125.69(18) . . yes C4A C8A C8 115.90(18) . . ? C4A C8A C1 114.94(18) . . ? C8 C8A C1 129.16(18) . . yes C4 C9 C10 105.0(2) . . ? C5 C10 C9 105.0(2) . . ? C16 C11 C12 117.97(19) . . ? C16 C11 C8 121.55(18) . . ? C12 C11 C8 120.37(18) . . ? C13 C12 C11 123.86(19) . . ? C12 C13 C14 116.02(19) . . ? C12 C13 C17 120.56(19) . . ? C14 C13 C17 123.36(19) . . ? O1 C14 C13 119.11(19) . . ? O1 C14 C15 118.54(19) . . ? C13 C14 C15 122.25(19) . . ? C16 C15 C14 118.46(19) . . ? C16 C15 C22 119.0(2) . . ? C14 C15 C22 122.6(2) . . ? C11 C16 C15 121.30(19) . . ? C18 C17 C20 106.7(2) . . ? C18 C17 C13 108.9(2) . . ? C20 C17 C13 111.9(2) . . ? C18 C17 C19 110.1(2) . . ? C20 C17 C19 106.7(2) . . ? C13 C17 C19 112.4(2) . . ? C24 C23 C28 118.41(19) . . ? C24 C23 C1 121.02(18) . . ? C28 C23 C1 120.44(18) . . ? C23 C24 C25 123.1(2) . . ? C24 C25 C26 115.60(19) . . ? C24 C25 C29 121.1(2) . . ? C26 C25 C29 123.2(2) . . ? O2 C26 C27 118.59(19) . . ? O2 C26 C25 118.74(19) . . ? C27 C26 C25 122.53(19) . . ? C28 C27 C26 118.4(2) . . ? C28 C27 C34 119.2(2) . . ? C26 C27 C34 122.2(2) . . ? C27 C28 C23 121.5(2) . . ? C32 C29 C30 108.0(2) . . ? C32 C29 C25 112.0(2) . . ? C30 C29 C25 112.0(2) . . ? C32 C29 C31 109.4(2) . . ? C30 C29 C31 107.0(2) . . ? C25 C29 C31 108.2(2) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 65.09 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.159 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.040 #============================================================ #============================================================ data_DiMe.cif _database_code_CSD 145453 _publ_section_synopsis ; ? ; _publ_section_abstract ; X-ray structural analysis confirms that the title compound, 5,6-Di(3-tert-butyl-4-methoxy-5-methylphenyl)acenaphthene, C~36~H~42~O~2~, exhibits the expected anti-geometry. The two phenyl rings have been rotated by -53.7(2) and -55.7(2) \% away from the acenaphthene plane along the linking bonds, allowing the bulky t-butyl substituents to project into relatively uncrowded regions. The overall molecular geometry is near to C~2~ symmetry, except for the O-Me groups, only one of which can be accommodated above the molecular cavity. ; _publ_section_comment ; The 5,6-diphenylacenaphthene conformation in the title molecule (I) is close to that of the unsubstituted parent molecule (II) (Clough, Kung, Marsh and Roberts, 1976), as exemplified by the similarity of their inter ring torsion angles ( -57.0 and -57.3 \% cf Abstract). A closer approach to co-planarity is prevented by clashes between phenyl carbons, in particular the linking carbons and ortho-carbons on adjacent phenyl rings ( C...C 3.062(6) and 3.010(6) /%A in the title molecule and 3.039 and 3.041 /%A in 5,6-diphenylacenaphthene). Also, in both molecules, this clash is reduced by twisting the acenaphthene frame slightly so that the phenyl rings project to either side of the plane (phenyl carbon to the acenaphthene plane [C(2)-C(4a)-C(7)] distances in the title molecule are 0.199 and -0.272 /%A cf 0.198 and -0.163 /%A in the parent molecule). These close similarities suggest that the ambient molecular configuration is governed primarily by interactions within the diphenylacenaphthene core and is only marginally influenced by substituents in the meta and para positions. ; _publ_section_acknowledgements ; We thank the EPSRC for a grant (GR/97311210) to MS. ; _publ_section_exptl_prep ; A rotaflo flask was charged with 3-tert-butyl-4-methoxy-5-methylphenylboronic acid (3.68 mmol), 5,6-dibromoacenaphthene (1.602 mmol), barium hydroxide hydrate (4.608 mmol), dimethylacetamide (15 ml) and water (3 ml). The resulting mixture was then THOROUGHLY degassed using a pump-freeze-thaw method (three cycles). Upon addition of (tetrakistriphenylphosphonium)palladium(0) (0.16 mmol), the degasing procedure was repeated and the mixture heated to 80 /% C for 48 h before quenching with 1.5 M HCl (15 ml). The resulting mixture was extracted with dichloromethane, the organic phase was washed with 1.5 M HCl (10 cm3 x 4), dried (magnesium sulfate) and evaporated. Purification by silica gel chromatography with hexane as an eluent gave the title compound which was crystallised for single crystal diffraction by slow evaporation from a mixture of diethyl ether and ethanol. ; _publ_section_references ; Burnett, M.N. and Johnson, C.K. (1996) ORTEP-III Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee. Clough, R.L., Kung, W.J., Marsh, R.E and Roberts, J.D. (1976) J. Org. Chem., 41, 3603-3608. Farrugia, L.J. (1997) ORTEP3 for Windows, J. Appl. Cryst. 30, 565. International Tables for Crystallography (1992). Vol. C. Dordrecht: Kluwer Academic Publishers. Molecular Structure Corporation (1985) TEXSAN. TEXRAY Structure Analysis Package. MSC, 3200A Research Forest Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1997) SHELX97. Programs for Crystal Structure Analysis (Release 97-2). Univ. of Gottingen, Germany. ; _publ_section_figure_captions ; Figure 1. The title molecule, including atomic numbering scheme, drawn using ORTEPIII (Burnett and Johnson, 1996; Farrugia, 1997) ; #***** REMEMBER ***** QUASAR ***** CYCLOPS ****** # _atom_type_scat_source # ; # InternationalTables for X-ray Crystallography (1992) # ; #============================================================ #============================================================ #DiMe.cif #data_h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 O2' _chemical_formula_weight 394.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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 10.547(2) _cell_length_b 11.975(2) _cell_length_c 9.011(3) _cell_angle_alpha 111.51(2) _cell_angle_beta 92.85(2) _cell_angle_gamma 88.69(2) _cell_volume 1057.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.594 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8418 _exptl_absorpt_correction_T_max 0.9430 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7038 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 65.08 _reflns_number_total 3462 _reflns_number_gt 2156 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.8268P] 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 SHELXL _refine_ls_extinction_coef 0.0005(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3462 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2586 _refine_ls_wR_factor_gt 0.2216 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0949(3) 0.2135(3) 0.7227(4) 0.0892(11) Uani 1 d . . . O2 O 0.7881(3) 0.4742(3) 0.9411(3) 0.0827(10) Uani 1 d . . . C1 C 0.7714(4) 0.1337(3) 0.1757(4) 0.0534(10) Uani 1 d . . . C2 C 0.8124(4) 0.0531(4) 0.0309(5) 0.0668(12) Uani 1 d . . . C3 C 0.7431(5) 0.0214(4) -0.1150(5) 0.0690(12) Uani 1 d . . . C4A C 0.5818(4) 0.1552(3) 0.0248(4) 0.0530(10) Uani 1 d . . . C4 C 0.6267(4) 0.0702(3) -0.1181(4) 0.0580(10) Uani 1 d . . . C5 C 0.4610(4) 0.1981(3) -0.0007(5) 0.0575(10) Uani 1 d . . . C6 C 0.4063(4) 0.2850(4) 0.1233(5) 0.0678(12) Uani 1 d . . . C7 C 0.4729(4) 0.3251(4) 0.2728(5) 0.0630(11) Uani 1 d . . . C8A C 0.6501(3) 0.1912(3) 0.1744(4) 0.0488(9) Uani 1 d . . . C8 C 0.5888(3) 0.2835(3) 0.3038(4) 0.0511(9) Uani 1 d . . . C9 C 0.5290(5) 0.0539(5) -0.2519(6) 0.0721(12) Uani 1 d . . . C10 C 0.4164(5) 0.1351(5) -0.1747(6) 0.0725(13) Uani 1 d . . . C11 C 0.8543(4) 0.1499(3) 0.3186(5) 0.0544(10) Uani 1 d . . . C12 C 0.9788(4) 0.1915(4) 0.3315(5) 0.0618(11) Uani 1 d . . . C13 C 1.0588(4) 0.2111(4) 0.4640(5) 0.0659(11) Uani 1 d . . . C14 C 1.0126(4) 0.1874(4) 0.5910(5) 0.0684(12) Uani 1 d . . . C15 C 0.8924(4) 0.1415(4) 0.5822(5) 0.0658(11) Uani 1 d . . . C16 C 0.8152(4) 0.1222(3) 0.4459(5) 0.0565(10) Uani 1 d . . . C17 C 1.1911(5) 0.2598(6) 0.4751(8) 0.0892(16) Uani 1 d . . . C18 C 1.0472(8) 0.2031(8) 0.8630(8) 0.111(2) Uani 1 d . . . C19 C 0.6424(3) 0.3350(3) 0.4712(4) 0.0531(9) Uani 1 d . . . C20 C 0.7551(4) 0.3978(3) 0.5138(5) 0.0562(10) Uani 1 d . . . C21 C 0.8040(4) 0.4439(3) 0.6722(5) 0.0597(10) Uani 1 d . . . C22 C 0.7336(4) 0.4261(4) 0.7876(5) 0.0633(11) Uani 1 d . . . C23 C 0.6211(4) 0.3673(4) 0.7512(5) 0.0683(12) Uani 1 d . . . C24 C 0.5756(4) 0.3224(4) 0.5938(5) 0.0636(11) Uani 1 d . . . C25 C 0.9288(5) 0.5074(5) 0.7157(7) 0.0802(14) Uani 1 d . . . C26 C 0.7213(8) 0.4604(11) 1.0686(8) 0.122(3) Uani 1 d . . . H2 H 0.902(4) 0.027(3) 0.045(4) 0.051(10) Uiso 1 d . . . H3 H 0.778(5) -0.032(4) -0.204(6) 0.087(15) Uiso 1 d . . . H6 H 0.322(5) 0.313(4) 0.117(5) 0.076(13) Uiso 1 d . . . H7 H 0.432(4) 0.386(4) 0.356(5) 0.060(11) Uiso 1 d . . . H9A H 0.567(5) 0.082(4) -0.334(6) 0.091(15) Uiso 1 d . . . H9B H 0.495(5) -0.031(5) -0.289(6) 0.088(15) Uiso 1 d . . . H10B H 0.343(4) 0.091(4) -0.176(5) 0.065(12) Uiso 1 d . . . H10A H 0.401(4) 0.197(4) -0.222(5) 0.066(12) Uiso 1 d . . . H12 H 0.998(3) 0.214(3) 0.244(4) 0.052(10) Uiso 1 d . . . H15 H 0.870(3) 0.124(3) 0.684(5) 0.053(10) Uiso 1 d . . . H16 H 0.723(4) 0.094(3) 0.443(4) 0.051(10) Uiso 1 d . . . H17A H 1.211(7) 0.274(7) 0.376(9) 0.16(3) Uiso 1 d . . . H17B H 1.214(6) 0.349(6) 0.606(7) 0.13(2) Uiso 1 d . . . H17C H 1.264(6) 0.203(5) 0.493(7) 0.117(19) Uiso 1 d . . . H18A H 0.953(8) 0.256(7) 0.893(9) 0.17(3) Uiso 1 d . . . H18B H 1.130(7) 0.217(6) 0.936(8) 0.14(2) Uiso 1 d . . . H18C H 1.023(8) 0.103(8) 0.824(9) 0.18(3) Uiso 1 d . . . H20 H 0.798(3) 0.410(3) 0.429(4) 0.045(9) Uiso 1 d . . . H23 H 0.571(5) 0.362(4) 0.842(6) 0.086(14) Uiso 1 d . . . H24 H 0.499(6) 0.269(6) 0.550(7) 0.13(2) Uiso 1 d . . . H25A H 0.930(7) 0.577(7) 0.851(9) 0.17(3) Uiso 1 d . . . H25B H 0.971(6) 0.509(6) 0.622(7) 0.12(2) Uiso 1 d . . . H25C H 1.013(8) 0.461(8) 0.741(9) 0.18(3) Uiso 1 d . . . H26A H 0.614(8) 0.500(7) 1.059(8) 0.16(3) Uiso 1 d . . . H26B H 0.785(7) 0.512(6) 1.166(8) 0.14(2) Uiso 1 d . . . H26C H 0.703(8) 0.377(8) 1.046(9) 0.17(4) Uiso 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 O1 0.077(2) 0.104(3) 0.076(2) 0.0227(18) -0.0083(18) 0.0109(19) O2 0.088(2) 0.096(2) 0.0562(18) 0.0186(16) 0.0013(16) -0.0073(18) C1 0.053(2) 0.048(2) 0.057(2) 0.0156(17) 0.0169(18) 0.0093(17) C2 0.060(3) 0.062(3) 0.073(3) 0.018(2) 0.017(2) 0.016(2) C3 0.080(3) 0.060(3) 0.057(3) 0.009(2) 0.023(2) 0.011(2) C4A 0.062(2) 0.045(2) 0.053(2) 0.0174(17) 0.0123(18) -0.0019(17) C4 0.071(3) 0.052(2) 0.048(2) 0.0126(17) 0.0132(19) 0.0007(19) C5 0.056(2) 0.054(2) 0.064(2) 0.0239(19) 0.0010(19) -0.0053(18) C6 0.056(2) 0.065(3) 0.075(3) 0.017(2) 0.000(2) 0.013(2) C7 0.061(2) 0.059(2) 0.061(3) 0.011(2) 0.017(2) 0.014(2) C8A 0.055(2) 0.0406(19) 0.052(2) 0.0182(16) 0.0121(17) 0.0011(16) C8 0.049(2) 0.046(2) 0.057(2) 0.0160(17) 0.0081(17) 0.0030(16) C9 0.085(3) 0.070(3) 0.060(3) 0.021(2) 0.001(2) -0.008(2) C10 0.079(3) 0.073(3) 0.064(3) 0.024(2) -0.004(2) -0.009(3) C11 0.050(2) 0.0422(19) 0.064(2) 0.0119(17) 0.0092(18) 0.0104(16) C12 0.061(3) 0.054(2) 0.065(3) 0.014(2) 0.018(2) 0.0091(19) C13 0.053(2) 0.057(2) 0.075(3) 0.009(2) 0.010(2) 0.0105(19) C14 0.069(3) 0.060(3) 0.066(3) 0.013(2) 0.001(2) 0.018(2) C15 0.074(3) 0.059(2) 0.063(3) 0.020(2) 0.008(2) 0.009(2) C16 0.060(2) 0.049(2) 0.062(2) 0.0208(18) 0.0077(19) 0.0052(18) C17 0.059(3) 0.099(4) 0.095(4) 0.017(3) 0.013(3) -0.003(3) C18 0.104(5) 0.154(7) 0.082(4) 0.053(4) -0.010(4) 0.009(5) C19 0.051(2) 0.046(2) 0.055(2) 0.0093(17) 0.0156(17) 0.0121(16) C20 0.061(2) 0.045(2) 0.058(2) 0.0120(18) 0.017(2) 0.0050(18) C21 0.058(2) 0.041(2) 0.075(3) 0.0144(19) 0.009(2) 0.0031(17) C22 0.072(3) 0.055(2) 0.056(2) 0.0111(18) 0.017(2) 0.005(2) C23 0.068(3) 0.078(3) 0.059(3) 0.023(2) 0.014(2) 0.001(2) C24 0.057(2) 0.065(3) 0.064(3) 0.016(2) 0.011(2) 0.004(2) C25 0.073(3) 0.083(3) 0.075(3) 0.016(3) 0.014(3) -0.016(3) C26 0.120(6) 0.187(8) 0.064(4) 0.049(4) -0.003(3) -0.046(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 O1 C14 1.377(5) . ? O1 C18 1.431(7) . ? O2 C22 1.388(5) . ? O2 C26 1.437(7) . ? C1 C2 1.391(5) . ? C1 C8A 1.441(5) . ? C1 C11 1.474(6) . ? C2 C3 1.399(6) . ? C3 C4 1.351(6) . ? C4A C5 1.403(5) . ? C4A C4 1.412(5) . ? C4A C8A 1.419(5) . ? C4 C9 1.506(6) . ? C5 C6 1.359(6) . ? C5 C10 1.525(6) . ? C6 C7 1.409(6) . ? C7 C8 1.364(6) . ? C8A C8 1.448(5) . ? C8 C19 1.491(5) . ? C9 C10 1.541(7) . ? C11 C16 1.389(5) . ? C11 C12 1.399(5) . ? C12 C13 1.377(6) . ? C13 C14 1.389(6) . ? C13 C17 1.509(6) . ? C14 C15 1.380(6) . ? C15 C16 1.388(6) . ? C19 C20 1.382(5) . ? C19 C24 1.395(5) . ? C20 C21 1.404(6) . ? C21 C22 1.387(6) . ? C21 C25 1.497(6) . ? C22 C23 1.356(6) . ? C23 C24 1.384(6) . ? 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 C14 O1 C18 117.2(5) . . ? C22 O2 C26 117.9(4) . . ? C2 C1 C8A 117.5(4) . . ? C2 C1 C11 116.9(3) . . ? C8A C1 C11 125.5(3) . . ? C1 C2 C3 124.8(4) . . ? C4 C3 C2 118.8(4) . . ? C5 C4A C4 111.1(4) . . ? C5 C4A C8A 124.7(3) . . ? C4 C4A C8A 124.2(4) . . ? C3 C4 C4A 118.7(4) . . ? C3 C4 C9 131.9(4) . . ? C4A C4 C9 109.4(4) . . ? C6 C5 C4A 118.8(4) . . ? C6 C5 C10 131.7(4) . . ? C4A C5 C10 109.5(4) . . ? C5 C6 C7 118.0(4) . . ? C8 C7 C6 125.1(4) . . ? C4A C8A C1 115.9(3) . . ? C4A C8A C8 114.9(3) . . ? C1 C8A C8 129.2(3) . . ? C7 C8 C8A 118.5(4) . . ? C7 C8 C19 117.1(3) . . ? C8A C8 C19 124.4(3) . . ? C4 C9 C10 105.5(4) . . ? C5 C10 C9 104.3(4) . . ? C16 C11 C12 116.2(4) . . ? C16 C11 C1 122.3(4) . . ? C12 C11 C1 121.5(4) . . ? C13 C12 C11 123.7(4) . . ? C12 C13 C14 117.7(4) . . ? C12 C13 C17 122.0(5) . . ? C14 C13 C17 120.3(5) . . ? O1 C14 C15 123.9(4) . . ? O1 C14 C13 115.0(4) . . ? C15 C14 C13 121.1(4) . . ? C14 C15 C16 119.4(4) . . ? C15 C16 C11 121.9(4) . . ? C20 C19 C24 117.1(4) . . ? C20 C19 C8 123.5(3) . . ? C24 C19 C8 119.3(4) . . ? C19 C20 C21 122.2(4) . . ? C22 C21 C20 117.5(4) . . ? C22 C21 C25 120.8(4) . . ? C20 C21 C25 121.7(4) . . ? C23 C22 C21 122.1(4) . . ? C23 C22 O2 123.9(4) . . ? C21 C22 O2 114.1(4) . . ? C22 C23 C24 119.2(4) . . ? C23 C24 C19 121.9(4) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 65.08 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.383 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.047 data_mw97a _database_code_CSD 100797 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 O' _chemical_formula_weight 239.32 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 'C2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.426(11) _cell_length_b 12.426(10) _cell_length_c 15.224(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.59(6) _cell_angle_gamma 90.00 _cell_volume 2766(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9795 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2548 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.12 _reflns_number_total 2451 _reflns_number_gt 1288 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0743P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2451 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1403 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33474(16) 0.88904(17) 0.10230(15) 0.0626(7) Uani 1 d . . . C1 C 0.36485(19) 0.7838(2) 0.11653(19) 0.0438(7) Uani 1 d . . . C2 C 0.35129(18) 0.7294(2) 0.19229(18) 0.0394(7) Uani 1 d . . . C3 C 0.38336(17) 0.6242(2) 0.20616(19) 0.0371(7) Uani 1 d . . . C4 C 0.42677(17) 0.5722(2) 0.15001(17) 0.0380(7) Uani 1 d . . . C5 C 0.4373(2) 0.6291(3) 0.0767(2) 0.0458(8) Uani 1 d . . . C6 C 0.4071(2) 0.7350(3) 0.0598(2) 0.0490(8) Uani 1 d . . . C7 C 0.45088(18) 0.4560(2) 0.16311(18) 0.0396(7) Uani 1 d . . . C8 C 0.5000 0.4062(3) 0.2500 0.0360(9) Uani 1 d S . . C9 C 0.5000 0.2925(3) 0.2500 0.0409(10) Uani 1 d S . . C10 C 0.4631(2) 0.2286(2) 0.1709(2) 0.0490(8) Uani 1 d . . . C11 C 0.4229(2) 0.2776(3) 0.0875(2) 0.0522(8) Uani 1 d . . . C12 C 0.4164(2) 0.3904(3) 0.0861(2) 0.0483(8) Uani 1 d . . . C13 C 0.4777(4) 0.1118(3) 0.1973(3) 0.0716(11) Uani 1 d . . . C14 C 0.3021(2) 0.7806(2) 0.2552(2) 0.0493(8) Uani 1 d . . . C15 C 0.2053(3) 0.8175(4) 0.1982(3) 0.0766(12) Uani 1 d . . . C16 C 0.2931(3) 0.7012(4) 0.3284(3) 0.0676(11) Uani 1 d . . . C17 C 0.3580(3) 0.8776(4) 0.3062(3) 0.0733(11) Uani 1 d . . . C18 C 0.3257(4) 0.9377(3) 0.0158(3) 0.0731(12) Uani 1 d . . . H3 H 0.3721(18) 0.581(2) 0.2590(19) 0.050(8) Uiso 1 d . . . H5 H 0.4631(16) 0.5991(19) 0.0325(17) 0.033(7) Uiso 1 d . . . H6 H 0.414(2) 0.771(2) 0.004(2) 0.060(9) Uiso 1 d . . . H11 H 0.399(2) 0.236(2) 0.032(2) 0.050(8) Uiso 1 d . . . H12 H 0.382(2) 0.423(2) 0.027(2) 0.050(8) Uiso 1 d . . . H13A H 0.427(3) 0.066(4) 0.180(3) 0.110(16) Uiso 1 d . . . H13B H 0.515(3) 0.079(4) 0.161(3) 0.132(18) Uiso 1 d . . . H15A H 0.172(3) 0.744(4) 0.173(3) 0.110(16) Uiso 1 d . . . H15B H 0.177(3) 0.851(3) 0.237(3) 0.099(14) Uiso 1 d . . . H15C H 0.211(3) 0.877(4) 0.151(3) 0.116(16) Uiso 1 d . . . H16A H 0.264(3) 0.736(3) 0.371(2) 0.085(12) Uiso 1 d . . . H16B H 0.254(3) 0.643(3) 0.296(3) 0.092(14) Uiso 1 d . . . H16C H 0.361(3) 0.672(3) 0.373(3) 0.110(14) Uiso 1 d . . . H17A H 0.367(3) 0.937(3) 0.262(3) 0.096(14) Uiso 1 d . . . H17B H 0.328(3) 0.906(3) 0.355(3) 0.115(15) Uiso 1 d . . . H17C H 0.422(3) 0.854(3) 0.345(3) 0.097(14) Uiso 1 d . . . H18A H 0.293(3) 0.886(3) -0.036(3) 0.089(12) Uiso 1 d . . . H18B H 0.296(2) 1.015(3) 0.018(2) 0.083(11) Uiso 1 d . . . H18C H 0.389(3) 0.948(3) 0.009(3) 0.104(15) Uiso 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 O1 0.0772(16) 0.0444(14) 0.0634(15) 0.0110(11) 0.0186(12) 0.0083(11) C1 0.0403(16) 0.0378(17) 0.0458(17) 0.0037(14) 0.0031(13) 0.0016(13) C2 0.0305(15) 0.0469(18) 0.0381(15) -0.0037(13) 0.0072(12) -0.0024(13) C3 0.0327(15) 0.0415(17) 0.0374(16) 0.0017(13) 0.0118(12) -0.0021(12) C4 0.0351(15) 0.0445(17) 0.0328(14) -0.0009(12) 0.0087(12) 0.0018(12) C5 0.0477(18) 0.055(2) 0.0387(16) 0.0009(14) 0.0189(14) 0.0045(15) C6 0.0529(19) 0.055(2) 0.0401(17) 0.0093(15) 0.0163(15) -0.0005(15) C7 0.0388(15) 0.0452(18) 0.0372(16) -0.0010(13) 0.0156(13) 0.0031(13) C8 0.034(2) 0.038(2) 0.038(2) 0.000 0.0146(17) 0.000 C9 0.040(2) 0.039(2) 0.045(2) 0.000 0.0165(19) 0.000 C10 0.0492(18) 0.0467(19) 0.0525(18) -0.0071(15) 0.0179(15) -0.0015(15) C11 0.059(2) 0.051(2) 0.0428(17) -0.0132(16) 0.0119(16) -0.0011(16) C12 0.0525(19) 0.053(2) 0.0351(16) -0.0001(15) 0.0080(14) 0.0103(15) C13 0.092(3) 0.038(2) 0.076(2) -0.0051(17) 0.014(2) -0.002(2) C14 0.0436(18) 0.0539(19) 0.0504(18) -0.0092(15) 0.0148(14) 0.0040(14) C15 0.049(2) 0.099(3) 0.082(3) -0.006(3) 0.022(2) 0.022(2) C16 0.075(3) 0.081(3) 0.061(2) -0.004(2) 0.042(2) 0.005(2) C17 0.083(3) 0.067(3) 0.068(3) -0.023(2) 0.022(2) -0.005(2) C18 0.090(3) 0.051(2) 0.064(3) 0.020(2) 0.004(2) 0.006(2) _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 O1 C1 1.381(4) . ? O1 C18 1.414(4) . ? C1 C6 1.377(4) . ? C1 C2 1.409(4) . ? C2 C3 1.390(4) . ? C2 C14 1.536(4) . ? C3 C4 1.401(4) . ? C4 C5 1.374(4) . ? C4 C7 1.488(4) . ? C5 C6 1.393(4) . ? C7 C12 1.387(4) . ? C7 C8 1.438(3) . ? C8 C9 1.412(5) . ? C8 C7 1.438(3) 2_655 ? C9 C10 1.403(4) . ? C9 C10 1.403(4) 2_655 ? C10 C11 1.367(4) . ? C10 C13 1.503(5) . ? C11 C12 1.406(4) . ? C13 C13 1.531(8) 2_655 ? C14 C16 1.527(5) . ? C14 C15 1.538(5) . ? C14 C17 1.540(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C18 118.6(3) . . ? C6 C1 O1 121.4(3) . . ? C6 C1 C2 121.7(3) . . ? O1 C1 C2 116.9(3) . . ? C3 C2 C1 115.9(3) . . ? C3 C2 C14 121.1(3) . . ? C1 C2 C14 122.9(3) . . ? C2 C3 C4 123.9(3) . . ? C5 C4 C3 117.5(3) . . ? C5 C4 C7 121.3(2) . . ? C3 C4 C7 120.9(2) . . ? C4 C5 C6 121.1(3) . . ? C1 C6 C5 119.9(3) . . ? C12 C7 C8 118.2(3) . . ? C12 C7 C4 116.4(2) . . ? C8 C7 C4 125.2(2) . . ? C9 C8 C7 115.52(18) . 2_655 ? C9 C8 C7 115.52(18) . . ? C7 C8 C7 129.0(4) 2_655 . ? C10 C9 C10 111.0(4) . 2_655 ? C10 C9 C8 124.51(19) . . ? C10 C9 C8 124.51(19) 2_655 . ? C11 C10 C9 119.0(3) . . ? C11 C10 C13 131.5(3) . . ? C9 C10 C13 109.4(3) . . ? C10 C11 C12 117.9(3) . . ? C7 C12 C11 124.6(3) . . ? C10 C13 C13 105.00(19) . 2_655 ? C16 C14 C2 111.4(3) . . ? C16 C14 C15 107.8(3) . . ? C2 C14 C15 110.8(3) . . ? C16 C14 C17 107.7(3) . . ? C2 C14 C17 109.3(3) . . ? C15 C14 C17 109.8(3) . . ? 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 C18 O1 C1 C6 16.4(4) . . . . ? C18 O1 C1 C2 -164.4(3) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? O1 C1 C2 C3 -179.1(2) . . . . ? C6 C1 C2 C14 -178.3(3) . . . . ? O1 C1 C2 C14 2.4(4) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C14 C2 C3 C4 178.5(2) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C2 C3 C4 C7 -173.7(2) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C7 C4 C5 C6 174.2(3) . . . . ? O1 C1 C6 C5 179.4(3) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C5 C4 C7 C12 -49.0(4) . . . . ? C3 C4 C7 C12 124.0(3) . . . . ? C5 C4 C7 C8 136.3(3) . . . . ? C3 C4 C7 C8 -50.6(4) . . . . ? C12 C7 C8 C9 -6.4(3) . . . . ? C4 C7 C8 C9 168.2(2) . . . . ? C12 C7 C8 C7 173.6(3) . . . 2_655 ? C4 C7 C8 C7 -11.8(2) . . . 2_655 ? C7 C8 C9 C10 -174.25(19) 2_655 . . . ? C7 C8 C9 C10 5.75(19) . . . . ? C7 C8 C9 C10 5.75(19) 2_655 . . 2_655 ? C7 C8 C9 C10 -174.25(19) . . . 2_655 ? C10 C9 C10 C11 179.1(3) 2_655 . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C10 C9 C10 C13 -1.4(2) 2_655 . . . ? C8 C9 C10 C13 178.6(2) . . . . ? C9 C10 C11 C12 -3.2(5) . . . . ? C13 C10 C11 C12 177.5(4) . . . . ? C8 C7 C12 C11 2.7(4) . . . . ? C4 C7 C12 C11 -172.3(3) . . . . ? C10 C11 C12 C7 2.3(5) . . . . ? C11 C10 C13 C13 -177.0(4) . . . 2_655 ? C9 C10 C13 C13 3.6(6) . . . 2_655 ? C3 C2 C14 C16 -1.4(4) . . . . ? C1 C2 C14 C16 177.1(3) . . . . ? C3 C2 C14 C15 -121.4(3) . . . . ? C1 C2 C14 C15 57.1(4) . . . . ? C3 C2 C14 C17 117.5(3) . . . . ? C1 C2 C14 C17 -64.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.471 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.471 _refine_diff_density_max 0.230 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.042