data_C19H26O2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H26 O2' _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' 0.0181 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5973(10) _cell_length_b 7.2630(10) _cell_length_c 13.3032(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.863(9) _cell_angle_gamma 90.00 _cell_volume 830.24(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4939 _cell_measurement_theta_min 6.95 _cell_measurement_theta_max 65.16 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method none _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.562 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9204 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details ; Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'microfocus sealed tube' _diffrn_source_type 'Incoatec I\uS' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9045 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 65.43 _reflns_number_total 2711 _reflns_number_gt 2372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0465P)^2^+0.2406P] 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 0.0102(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _chemical_absolute_configuration unk _refine_ls_number_reflns 2711 _refine_ls_number_parameters 208 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.081 _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 O1 O 0.86330(18) 0.2367(3) 0.91305(13) 0.0291(4) Uani 1 1 d D . . H1O H 0.920(3) 0.290(4) 0.9573(19) 0.044 Uiso 1 1 d D . . O2 O 0.94493(19) 0.8730(3) 0.93722(14) 0.0322(5) Uani 1 1 d D . . H2O H 0.920(4) 0.991(3) 0.925(2) 0.048 Uiso 1 1 d D . . C1 C 0.7340(3) 0.3568(4) 0.88933(18) 0.0266(6) Uani 1 1 d D . . H1 H 0.646(3) 0.269(3) 0.8768(19) 0.032 Uiso 1 1 d D . . C2 C 0.7023(2) 0.4739(4) 0.98072(19) 0.0267(6) Uani 1 1 d . . . C3 C 0.6308(3) 0.3892(4) 1.06252(18) 0.0300(6) Uani 1 1 d . . . H3 H 0.5941 0.2661 1.0567 0.036 Uiso 1 1 calc R . . C4 C 0.6139(3) 0.4853(4) 1.1512(2) 0.0350(7) Uani 1 1 d . . . H4 H 0.5655 0.4279 1.2062 0.042 Uiso 1 1 calc R . . C5 C 0.6666(3) 0.6629(4) 1.1603(2) 0.0330(7) Uani 1 1 d . . . H5 H 0.6576 0.7268 1.2222 0.040 Uiso 1 1 calc R . . C6 C 0.7331(3) 0.7492(4) 1.0793(2) 0.0328(6) Uani 1 1 d . . . H6 H 0.7665 0.8736 1.0853 0.039 Uiso 1 1 calc R . . C7 C 0.7515(2) 0.6546(4) 0.98901(19) 0.0269(6) Uani 1 1 d . . . C8 C 0.8234(3) 0.7521(4) 0.90112(19) 0.0283(6) Uani 1 1 d D . . H8 H 0.744(3) 0.837(4) 0.8656(18) 0.034 Uiso 1 1 d D . . C9 C 0.8879(3) 0.6189(4) 0.82423(19) 0.0279(6) Uani 1 1 d D . . H9 H 0.976(3) 0.548(4) 0.8585(18) 0.033 Uiso 1 1 d D . . C10 C 0.7633(2) 0.4717(4) 0.79500(19) 0.0273(6) Uani 1 1 d . . . C11 C 0.9494(3) 0.7204(4) 0.7356(2) 0.0360(6) Uani 1 1 d . . . H11 H 0.8763 0.7818 0.6923 0.043 Uiso 1 1 calc R . . C12 C 1.0970(4) 0.7305(6) 0.7135(2) 0.0517(8) Uani 1 1 d . . . H12A H 1.1735 0.6708 0.7550 0.062 Uiso 1 1 calc R . . H12B H 1.1272 0.7974 0.6559 0.062 Uiso 1 1 calc R . . C13 C 0.8229(3) 0.3484(4) 0.70988(19) 0.0303(6) Uani 1 1 d . . . H13A H 0.8281 0.4236 0.6480 0.036 Uiso 1 1 calc R . . H13B H 0.9303 0.3089 0.7284 0.036 Uiso 1 1 calc R . . C14 C 0.7261(3) 0.1776(4) 0.6860(2) 0.0323(6) Uani 1 1 d . . . H14A H 0.7325 0.0927 0.7442 0.039 Uiso 1 1 calc R . . H14B H 0.6158 0.2139 0.6754 0.039 Uiso 1 1 calc R . . C15 C 0.7795(3) 0.0781(4) 0.5938(2) 0.0329(6) Uani 1 1 d . . . H15A H 0.8855 0.0942 0.5779 0.039 Uiso 1 1 calc R . . C16 C 0.6952(3) -0.0297(4) 0.5321(2) 0.0344(6) Uani 1 1 d . . . C17 C 0.5239(3) -0.0664(5) 0.5420(2) 0.0396(7) Uani 1 1 d . . . H17A H 0.5080 -0.1965 0.5583 0.059 Uiso 1 1 calc R . . H17B H 0.4687 -0.0371 0.4784 0.059 Uiso 1 1 calc R . . H17C H 0.4835 0.0106 0.5958 0.059 Uiso 1 1 calc R . . C18 C 0.7679(4) -0.1300(5) 0.4464(2) 0.0494(8) Uani 1 1 d . . . H18A H 0.8799 -0.1042 0.4470 0.074 Uiso 1 1 calc R . . H18B H 0.7200 -0.0884 0.3826 0.074 Uiso 1 1 calc R . . H18C H 0.7514 -0.2627 0.4539 0.074 Uiso 1 1 calc R . . C19 C 0.6090(3) 0.5621(4) 0.7597(2) 0.0318(6) Uani 1 1 d . . . H19A H 0.5330 0.4662 0.7415 0.048 Uiso 1 1 calc R . . H19B H 0.6269 0.6399 0.7010 0.048 Uiso 1 1 calc R . . H19C H 0.5690 0.6377 0.8141 0.048 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 O1 0.0224(8) 0.0259(11) 0.0387(10) -0.0039(9) -0.0027(7) 0.0020(8) O2 0.0266(9) 0.0226(11) 0.0471(11) 0.0012(9) -0.0060(7) -0.0033(8) C1 0.0190(11) 0.0230(15) 0.0376(14) -0.0033(12) -0.0012(9) -0.0002(10) C2 0.0138(10) 0.0270(16) 0.0391(14) -0.0003(11) -0.0022(9) 0.0035(10) C3 0.0195(11) 0.0299(17) 0.0405(15) -0.0009(12) 0.0021(10) -0.0014(10) C4 0.0210(12) 0.0440(19) 0.0404(15) 0.0010(13) 0.0047(10) 0.0025(13) C5 0.0220(12) 0.0383(18) 0.0386(15) -0.0075(12) 0.0015(10) 0.0039(12) C6 0.0192(11) 0.0304(16) 0.0485(16) -0.0086(13) -0.0032(10) 0.0003(11) C7 0.0151(10) 0.0286(17) 0.0368(14) -0.0008(11) -0.0028(9) 0.0037(11) C8 0.0188(11) 0.0210(15) 0.0445(15) -0.0012(12) -0.0063(10) -0.0007(11) C9 0.0200(11) 0.0249(16) 0.0389(14) 0.0032(11) 0.0009(10) -0.0003(10) C10 0.0183(11) 0.0280(16) 0.0356(13) 0.0019(11) 0.0005(9) -0.0011(11) C11 0.0400(15) 0.0264(16) 0.0417(15) 0.0005(13) 0.0028(11) -0.0068(13) C12 0.0490(17) 0.057(2) 0.0492(17) 0.0010(17) 0.0095(13) -0.0195(17) C13 0.0244(12) 0.0305(16) 0.0361(14) -0.0012(12) 0.0025(10) -0.0006(11) C14 0.0277(12) 0.0310(17) 0.0386(15) -0.0047(12) 0.0045(10) -0.0015(11) C15 0.0278(13) 0.0317(16) 0.0394(14) -0.0021(13) 0.0061(11) -0.0003(11) C16 0.0374(13) 0.0285(17) 0.0375(15) 0.0005(12) 0.0017(11) 0.0028(13) C17 0.0389(14) 0.0388(18) 0.0408(15) 0.0003(13) -0.0053(12) -0.0018(13) C18 0.0514(18) 0.051(2) 0.0466(17) -0.0176(16) 0.0083(14) -0.0054(16) C19 0.0256(13) 0.0321(16) 0.0373(14) -0.0027(12) -0.0031(10) 0.0002(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.440(3) . ? O1 H1O 0.845(18) . ? O2 C8 1.435(3) . ? O2 H2O 0.897(18) . ? C1 C2 1.515(4) . ? C1 C10 1.535(4) . ? C1 H1 1.002(17) . ? C2 C7 1.382(4) . ? C2 C3 1.409(4) . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.371(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 C7 1.398(4) . ? C6 H6 0.9500 . ? C7 C8 1.516(4) . ? C8 C9 1.526(4) . ? C8 H8 1.028(17) . ? C9 C11 1.502(4) . ? C9 C10 1.554(3) . ? C9 H9 1.011(17) . ? C10 C19 1.539(3) . ? C10 C13 1.544(4) . ? C11 C12 1.313(4) . ? C11 H11 0.9500 . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? C13 C14 1.522(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.508(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.332(4) . ? C15 H15A 0.9500 . ? C16 C18 1.506(4) . ? C16 C17 1.506(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C1 O1 H1O 107(2) . . ? C8 O2 H2O 111(2) . . ? O1 C1 C2 108.76(18) . . ? O1 C1 C10 111.26(19) . . ? C2 C1 C10 112.9(2) . . ? O1 C1 H1 103.0(16) . . ? C2 C1 H1 109.7(15) . . ? C10 C1 H1 110.8(15) . . ? C7 C2 C3 119.5(2) . . ? C7 C2 C1 122.3(2) . . ? C3 C2 C1 118.0(2) . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 119.5(2) . . ? C2 C7 C8 120.9(2) . . ? C6 C7 C8 119.6(2) . . ? O2 C8 C7 109.78(19) . . ? O2 C8 C9 109.61(19) . . ? C7 C8 C9 112.8(2) . . ? O2 C8 H8 104.6(17) . . ? C7 C8 H8 110.7(15) . . ? C9 C8 H8 109.0(15) . . ? C11 C9 C8 111.1(2) . . ? C11 C9 C10 113.5(2) . . ? C8 C9 C10 109.96(19) . . ? C11 C9 H9 109.1(16) . . ? C8 C9 H9 107.7(16) . . ? C10 C9 H9 105.1(18) . . ? C1 C10 C19 108.59(19) . . ? C1 C10 C13 110.6(2) . . ? C19 C10 C13 109.1(2) . . ? C1 C10 C9 107.4(2) . . ? C19 C10 C9 111.3(2) . . ? C13 C10 C9 109.85(19) . . ? C12 C11 C9 124.8(3) . . ? C12 C11 H11 117.6 . . ? C9 C11 H11 117.6 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? C14 C13 C10 115.69(19) . . ? C14 C13 H13A 108.4 . . ? C10 C13 H13A 108.4 . . ? C14 C13 H13B 108.4 . . ? C10 C13 H13B 108.4 . . ? H13A C13 H13B 107.4 . . ? C15 C14 C13 112.4(2) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 127.5(2) . . ? C16 C15 H15A 116.2 . . ? C14 C15 H15A 116.2 . . ? C15 C16 C18 121.3(2) . . ? C15 C16 C17 124.3(2) . . ? C18 C16 C17 114.3(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 O1 C1 C2 C7 101.1(3) . . . . ? C10 C1 C2 C7 -22.9(3) . . . . ? O1 C1 C2 C3 -74.0(3) . . . . ? C10 C1 C2 C3 162.04(19) . . . . ? C7 C2 C3 C4 -1.7(3) . . . . ? C1 C2 C3 C4 173.5(2) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 1.9(4) . . . . ? C4 C5 C6 C7 -2.0(4) . . . . ? C3 C2 C7 C6 1.7(3) . . . . ? C1 C2 C7 C6 -173.3(2) . . . . ? C3 C2 C7 C8 -177.7(2) . . . . ? C1 C2 C7 C8 7.3(3) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? C5 C6 C7 C8 179.5(2) . . . . ? C2 C7 C8 O2 -143.7(2) . . . . ? C6 C7 C8 O2 36.9(3) . . . . ? C2 C7 C8 C9 -21.2(3) . . . . ? C6 C7 C8 C9 159.46(19) . . . . ? O2 C8 C9 C11 -60.7(3) . . . . ? C7 C8 C9 C11 176.65(19) . . . . ? O2 C8 C9 C10 172.7(2) . . . . ? C7 C8 C9 C10 50.1(3) . . . . ? O1 C1 C10 C19 167.0(2) . . . . ? C2 C1 C10 C19 -70.3(3) . . . . ? O1 C1 C10 C13 47.4(3) . . . . ? C2 C1 C10 C13 170.03(18) . . . . ? O1 C1 C10 C9 -72.5(2) . . . . ? C2 C1 C10 C9 50.2(2) . . . . ? C11 C9 C10 C1 169.8(2) . . . . ? C8 C9 C10 C1 -65.0(2) . . . . ? C11 C9 C10 C19 -71.4(3) . . . . ? C8 C9 C10 C19 53.7(3) . . . . ? C11 C9 C10 C13 49.5(3) . . . . ? C8 C9 C10 C13 174.6(2) . . . . ? C8 C9 C11 C12 111.8(3) . . . . ? C10 C9 C11 C12 -123.7(3) . . . . ? C1 C10 C13 C14 51.3(3) . . . . ? C19 C10 C13 C14 -68.1(3) . . . . ? C9 C10 C13 C14 169.7(2) . . . . ? C10 C13 C14 C15 172.6(2) . . . . ? C13 C14 C15 C16 -154.0(3) . . . . ? C14 C15 C16 C18 -175.9(3) . . . . ? C14 C15 C16 C17 2.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O2 0.845(18) 1.892(18) 2.730(2) 171(3) 2_747 O2 H2O O1 0.897(18) 1.855(19) 2.749(3) 175(3) 1_565 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 65.43 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.199 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.045