data_cd24440 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 O2' _chemical_formula_weight 286.40 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 28.423(3) _cell_length_b 6.5858(8) _cell_length_c 17.641(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.363(2) _cell_angle_gamma 90.00 _cell_volume 3275.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2312 _cell_measurement_theta_min 4.656 _cell_measurement_theta_max 54.604 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.432 _exptl_crystal_size_mid 0.409 _exptl_crystal_size_min 0.327 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.53641 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9178 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3565 _reflns_number_gt 2482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^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 SHELXL _refine_ls_extinction_coef 0.0007(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3565 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.25034(4) -0.05319(19) -0.06528(7) 0.0580(4) Uani 1 1 d . . . O2 O 0.32371(4) -0.03793(17) -0.00277(6) 0.0449(3) Uani 1 1 d . . . C1 C 0.27585(6) -0.0248(2) -0.00626(9) 0.0432(4) Uani 1 1 d . . . C2 C 0.26349(6) 0.0271(2) 0.06938(9) 0.0410(4) Uani 1 1 d . . . C3 C 0.30345(5) 0.0491(2) 0.11673(8) 0.0372(4) Uani 1 1 d . . . C4 C 0.34532(5) 0.0011(2) 0.07545(8) 0.0384(4) Uani 1 1 d . . . C5 C 0.38128(6) 0.1713(3) 0.07254(10) 0.0478(4) Uani 1 1 d . . . C6 C 0.42183(8) 0.1098(4) 0.02943(12) 0.0656(6) Uani 1 1 d . . . C7 C 0.44549(7) -0.0835(4) 0.06115(13) 0.0748(6) Uani 1 1 d . . . H7A H 0.4697 -0.1231 0.0299 0.090 Uiso 1 1 calc R . . H7B H 0.4609 -0.0586 0.1126 0.090 Uiso 1 1 calc R . . C8 C 0.41040(7) -0.2543(3) 0.06277(13) 0.0603(5) Uani 1 1 d . . . C9 C 0.36949(6) -0.1939(3) 0.10554(9) 0.0482(4) Uani 1 1 d . . . H9A H 0.3813 -0.1767 0.1592 0.058 Uiso 1 1 calc R . . H9B H 0.3463 -0.3027 0.1014 0.058 Uiso 1 1 calc R . . C10 C 0.21329(6) 0.0446(3) 0.08400(11) 0.0551(5) Uani 1 1 d . . . H10A H 0.2004 -0.0886 0.0892 0.083 Uiso 1 1 calc R . . H10B H 0.1952 0.1137 0.0420 0.083 Uiso 1 1 calc R . . H10C H 0.2119 0.1201 0.1302 0.083 Uiso 1 1 calc R . . C11 C 0.30785(5) 0.0983(2) 0.19940(8) 0.0392(4) Uani 1 1 d . . . C12 C 0.28977(7) -0.0274(3) 0.24651(11) 0.0542(5) Uani 1 1 d . . . C13 C 0.33027(6) 0.2932(3) 0.22433(9) 0.0399(4) Uani 1 1 d . . . C14 C 0.36518(6) 0.3234(2) 0.28053(8) 0.0402(4) Uani 1 1 d . . . C15 C 0.38338(7) 0.5319(3) 0.30168(12) 0.0521(5) Uani 1 1 d . . . C16 C 0.43626(7) 0.5496(3) 0.29964(13) 0.0697(6) Uani 1 1 d . . . H16A H 0.4470 0.6824 0.3183 0.084 Uiso 1 1 calc R . . H16B H 0.4430 0.5367 0.2473 0.084 Uiso 1 1 calc R . . C17 C 0.46283(9) 0.3868(4) 0.34830(17) 0.0810(7) Uani 1 1 d . . . C18 C 0.44450(7) 0.1788(4) 0.32525(15) 0.0807(7) Uani 1 1 d . . . H18A H 0.4606 0.0792 0.3598 0.097 Uiso 1 1 calc R . . H18B H 0.4519 0.1490 0.2742 0.097 Uiso 1 1 calc R . . C19 C 0.39151(7) 0.1591(3) 0.32617(12) 0.0576(5) Uani 1 1 d . . . H5A H 0.3942(6) 0.209(2) 0.1249(10) 0.048(4) Uiso 1 1 d . . . H5B H 0.3646(6) 0.287(3) 0.0502(10) 0.053(5) Uiso 1 1 d . . . H6A H 0.4451(7) 0.215(3) 0.0310(10) 0.065(6) Uiso 1 1 d . . . H6B H 0.4101(7) 0.096(3) -0.0233(11) 0.064(6) Uiso 1 1 d . . . H8A H 0.4258(7) -0.374(3) 0.0860(11) 0.064(6) Uiso 1 1 d . . . H8B H 0.3976(6) -0.293(3) 0.0095(11) 0.054(5) Uiso 1 1 d . . . H12A H 0.2916(7) 0.009(3) 0.3019(12) 0.066(6) Uiso 1 1 d . . . H12B H 0.2752(6) -0.147(3) 0.2289(9) 0.049(5) Uiso 1 1 d . . . H13 H 0.3173(5) 0.407(2) 0.1977(9) 0.041(4) Uiso 1 1 d . . . H15A H 0.3791(6) 0.560(3) 0.3524(11) 0.055(5) Uiso 1 1 d . . . H15B H 0.3658(7) 0.635(3) 0.2679(10) 0.061(5) Uiso 1 1 d . . . H17A H 0.4590(7) 0.417(3) 0.4008(13) 0.073(7) Uiso 1 1 d . . . H17B H 0.4974(9) 0.395(4) 0.3466(13) 0.097(7) Uiso 1 1 d . . . H19A H 0.3845(6) 0.167(3) 0.3766(12) 0.065(6) Uiso 1 1 d . . . H19B H 0.3801(7) 0.030(3) 0.3111(11) 0.061(6) Uiso 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 O1 0.0635(8) 0.0605(8) 0.0446(7) 0.0020(6) -0.0137(6) -0.0133(6) O2 0.0479(7) 0.0518(7) 0.0342(6) -0.0025(5) 0.0023(5) -0.0094(5) C1 0.0480(10) 0.0373(9) 0.0420(9) 0.0049(7) -0.0036(7) -0.0092(7) C2 0.0382(9) 0.0368(9) 0.0464(9) 0.0029(7) -0.0005(7) -0.0052(7) C3 0.0382(8) 0.0345(8) 0.0388(8) 0.0019(6) 0.0036(7) -0.0046(7) C4 0.0385(9) 0.0449(9) 0.0314(8) -0.0015(6) 0.0027(6) -0.0077(7) C5 0.0493(11) 0.0531(11) 0.0414(10) -0.0053(8) 0.0070(8) -0.0162(9) C6 0.0631(13) 0.0789(16) 0.0599(13) -0.0190(11) 0.0270(10) -0.0338(12) C7 0.0462(12) 0.0974(18) 0.0846(15) -0.0215(13) 0.0231(10) -0.0084(11) C8 0.0511(12) 0.0667(14) 0.0646(13) -0.0045(11) 0.0130(10) 0.0067(10) C9 0.0450(10) 0.0566(11) 0.0429(9) 0.0025(8) 0.0054(7) 0.0002(8) C10 0.0379(10) 0.0587(12) 0.0671(12) 0.0037(9) 0.0004(8) -0.0021(8) C11 0.0341(8) 0.0455(9) 0.0380(8) 0.0014(7) 0.0053(6) 0.0011(7) C12 0.0566(12) 0.0602(13) 0.0477(11) 0.0020(9) 0.0139(9) -0.0086(10) C13 0.0435(9) 0.0419(10) 0.0347(8) 0.0028(7) 0.0067(7) 0.0045(7) C14 0.0416(9) 0.0455(10) 0.0343(8) 0.0001(7) 0.0082(7) 0.0013(7) C15 0.0585(12) 0.0510(12) 0.0463(11) -0.0060(9) 0.0048(9) -0.0026(9) C16 0.0637(13) 0.0700(14) 0.0752(14) 0.0009(11) 0.0083(10) -0.0172(11) C17 0.0473(13) 0.101(2) 0.0910(19) 0.0025(15) -0.0062(12) -0.0121(12) C18 0.0541(13) 0.0813(16) 0.1004(17) 0.0097(13) -0.0146(11) 0.0112(11) C19 0.0609(13) 0.0547(13) 0.0524(12) 0.0085(9) -0.0103(9) -0.0015(10) _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 1.2047(18) . ? O2 C1 1.357(2) . ? O2 C4 1.4595(17) . ? C1 C2 1.463(2) . ? C2 C3 1.329(2) . ? C2 C10 1.487(2) . ? C3 C11 1.483(2) . ? C3 C4 1.506(2) . ? C4 C9 1.520(2) . ? C4 C5 1.522(2) . ? C5 C6 1.515(3) . ? C5 H5A 0.983(16) . ? C5 H5B 0.953(17) . ? C6 C7 1.513(3) . ? C6 H6A 0.95(2) . ? C6 H6B 0.951(19) . ? C7 C8 1.506(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.97(2) . ? C8 H8B 0.996(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.323(2) . ? C11 C13 1.475(2) . ? C12 H12A 1.00(2) . ? C12 H12B 0.922(18) . ? C13 C14 1.325(2) . ? C13 H13 0.935(16) . ? C14 C19 1.492(2) . ? C14 C15 1.498(2) . ? C15 C16 1.513(3) . ? C15 H15A 0.936(19) . ? C15 H15B 1.00(2) . ? C16 C17 1.513(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.503(3) . ? C17 H17A 0.97(2) . ? C17 H17B 0.99(3) . ? C18 C19 1.514(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.94(2) . ? C19 H19B 0.93(2) . ? 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 O2 C4 109.25(12) . . ? O1 C1 O2 121.22(16) . . ? O1 C1 C2 129.51(17) . . ? O2 C1 C2 109.27(13) . . ? C3 C2 C1 108.24(15) . . ? C3 C2 C10 130.13(16) . . ? C1 C2 C10 121.62(14) . . ? C2 C3 C11 126.83(15) . . ? C2 C3 C4 109.74(14) . . ? C11 C3 C4 123.28(13) . . ? O2 C4 C3 103.37(12) . . ? O2 C4 C9 107.34(12) . . ? C3 C4 C9 111.00(13) . . ? O2 C4 C5 107.50(12) . . ? C3 C4 C5 115.93(13) . . ? C9 C4 C5 111.02(14) . . ? C6 C5 C4 112.17(15) . . ? C6 C5 H5A 108.8(10) . . ? C4 C5 H5A 109.2(10) . . ? C6 C5 H5B 111.9(11) . . ? C4 C5 H5B 107.5(11) . . ? H5A C5 H5B 107.0(14) . . ? C7 C6 C5 111.71(17) . . ? C7 C6 H6A 108.9(11) . . ? C5 C6 H6A 111.2(12) . . ? C7 C6 H6B 111.5(12) . . ? C5 C6 H6B 108.8(12) . . ? H6A C6 H6B 104.6(16) . . ? C8 C7 C6 111.81(18) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 111.42(17) . . ? C7 C8 H8A 110.7(11) . . ? C9 C8 H8A 109.7(11) . . ? C7 C8 H8B 109.6(10) . . ? C9 C8 H8B 109.0(10) . . ? H8A C8 H8B 106.3(15) . . ? C8 C9 C4 112.87(15) . . ? C8 C9 H9A 109.0 . . ? C4 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C4 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 123.03(16) . . ? C12 C11 C3 119.37(16) . . ? C13 C11 C3 117.51(13) . . ? C11 C12 H12A 119.3(11) . . ? C11 C12 H12B 120.9(11) . . ? H12A C12 H12B 119.8(16) . . ? C14 C13 C11 127.40(15) . . ? C14 C13 H13 117.7(10) . . ? C11 C13 H13 114.8(10) . . ? C13 C14 C19 124.80(16) . . ? C13 C14 C15 121.72(15) . . ? C19 C14 C15 113.42(15) . . ? C14 C15 C16 112.15(16) . . ? C14 C15 H15A 109.6(11) . . ? C16 C15 H15A 104.9(11) . . ? C14 C15 H15B 110.3(11) . . ? C16 C15 H15B 110.9(11) . . ? H15A C15 H15B 108.8(16) . . ? C15 C16 C17 110.94(18) . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 111.20(19) . . ? C18 C17 H17A 111.6(13) . . ? C16 C17 H17A 106.8(13) . . ? C18 C17 H17B 110.8(14) . . ? C16 C17 H17B 111.6(14) . . ? H17A C17 H17B 104.6(17) . . ? C17 C18 C19 112.7(2) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C14 C19 C18 111.29(17) . . ? C14 C19 H19A 108.6(12) . . ? C18 C19 H19A 109.7(11) . . ? C14 C19 H19B 111.9(11) . . ? C18 C19 H19B 112.6(12) . . ? H19A C19 H19B 102.3(16) . . ? 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 C4 O2 C1 O1 -179.33(14) . . . . ? C4 O2 C1 C2 0.98(16) . . . . ? O1 C1 C2 C3 -178.29(17) . . . . ? O2 C1 C2 C3 1.37(17) . . . . ? O1 C1 C2 C10 2.6(3) . . . . ? O2 C1 C2 C10 -177.72(14) . . . . ? C1 C2 C3 C11 -178.88(15) . . . . ? C10 C2 C3 C11 0.1(3) . . . . ? C1 C2 C3 C4 -3.07(17) . . . . ? C10 C2 C3 C4 175.91(16) . . . . ? C1 O2 C4 C3 -2.65(15) . . . . ? C1 O2 C4 C9 114.75(13) . . . . ? C1 O2 C4 C5 -125.75(14) . . . . ? C2 C3 C4 O2 3.56(16) . . . . ? C11 C3 C4 O2 179.55(13) . . . . ? C2 C3 C4 C9 -111.24(15) . . . . ? C11 C3 C4 C9 64.75(18) . . . . ? C2 C3 C4 C5 120.90(15) . . . . ? C11 C3 C4 C5 -63.1(2) . . . . ? O2 C4 C5 C6 -64.5(2) . . . . ? C3 C4 C5 C6 -179.53(16) . . . . ? C9 C4 C5 C6 52.6(2) . . . . ? C4 C5 C6 C7 -54.2(2) . . . . ? C5 C6 C7 C8 54.9(2) . . . . ? C6 C7 C8 C9 -54.3(2) . . . . ? C7 C8 C9 C4 53.6(2) . . . . ? O2 C4 C9 C8 64.72(17) . . . . ? C3 C4 C9 C8 177.02(14) . . . . ? C5 C4 C9 C8 -52.50(19) . . . . ? C2 C3 C11 C12 61.1(2) . . . . ? C4 C3 C11 C12 -114.14(18) . . . . ? C2 C3 C11 C13 -115.62(18) . . . . ? C4 C3 C11 C13 69.10(19) . . . . ? C12 C11 C13 C14 53.8(3) . . . . ? C3 C11 C13 C14 -129.56(18) . . . . ? C11 C13 C14 C19 5.2(3) . . . . ? C11 C13 C14 C15 -177.62(15) . . . . ? C13 C14 C15 C16 -124.55(19) . . . . ? C19 C14 C15 C16 52.9(2) . . . . ? C14 C15 C16 C17 -53.7(2) . . . . ? C15 C16 C17 C18 54.6(3) . . . . ? C16 C17 C18 C19 -54.6(3) . . . . ? C13 C14 C19 C18 125.9(2) . . . . ? C15 C14 C19 C18 -51.5(2) . . . . ? C17 C18 C19 C14 52.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.197 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.040