data_x11179_cu _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 O2' _chemical_formula_weight 188.22 _chemical_absolute_configuration ad 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.2569(4) _cell_length_b 7.3867(5) _cell_length_c 20.2538(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 936.09(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9956 _cell_measurement_theta_min 4.37 _cell_measurement_theta_max 69.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7857 _exptl_absorpt_correction_T_max 0.9311 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_special_details ; Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. The instrument was purchased with the help of funding from the National Science Foundation (NSF) under Grant Number CHE-0946721. ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX2 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 12447 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 68.15 _reflns_number_total 1713 _reflns_number_gt 1711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2010.7.0 (Bruker-AXS, 2010)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2010)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 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^)+(0.0383P)^2^+0.2037P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(18) _refine_ls_number_reflns 1713 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.89243(13) 0.16202(11) 0.93139(4) 0.01765(19) Uani 1 1 d . . . C1 C 0.7316(2) 0.28305(16) 0.92552(5) 0.0180(3) Uani 1 1 d . . . O2 O 0.76499(14) 0.44293(11) 0.93126(4) 0.0238(2) Uani 1 1 d . . . C2 C 0.52366(19) 0.18700(16) 0.91311(5) 0.0183(3) Uani 1 1 d . . . H2A H 0.4384 0.2499 0.8789 0.022 Uiso 1 1 calc R . . H2B H 0.4380 0.1775 0.9541 0.022 Uiso 1 1 calc R . . C3 C 0.59612(18) 0.00116(16) 0.88934(5) 0.0166(2) Uani 1 1 d . . . H3 H 0.4908 -0.0957 0.9008 0.020 Uiso 1 1 calc R . . C4 C 0.65924(18) -0.00479(15) 0.81711(6) 0.0168(2) Uani 1 1 d . . . C5 C 0.54342(19) 0.05413(15) 0.76275(6) 0.0184(2) Uani 1 1 d . . . H5 H 0.4052 0.1052 0.7681 0.022 Uiso 1 1 calc R . . C6 C 0.6338(2) 0.03687(16) 0.70032(6) 0.0213(3) Uani 1 1 d . . . H6 H 0.5569 0.0772 0.6626 0.026 Uiso 1 1 calc R . . C7 C 0.8357(2) -0.03887(16) 0.69260(6) 0.0209(3) Uani 1 1 d . . . H7 H 0.8943 -0.0517 0.6496 0.025 Uiso 1 1 calc R . . C8 C 0.95335(19) -0.09621(15) 0.74723(6) 0.0201(3) Uani 1 1 d . . . H8 H 1.0915 -0.1475 0.7419 0.024 Uiso 1 1 calc R . . C9 C 0.86376(18) -0.07666(15) 0.80970(6) 0.0170(2) Uani 1 1 d . . . C10 C 0.95766(19) -0.12376(17) 0.87630(6) 0.0193(3) Uani 1 1 d . . . H10A H 1.1068 -0.0802 0.8800 0.023 Uiso 1 1 calc R . . H10B H 0.9549 -0.2562 0.8838 0.023 Uiso 1 1 calc R . . C11 C 0.81250(18) -0.02572(16) 0.92519(6) 0.0173(2) Uani 1 1 d . . . C12 C 0.7990(2) -0.10523(16) 0.99392(6) 0.0207(3) Uani 1 1 d . . . H12A H 0.6866 -0.0432 1.0189 0.031 Uiso 1 1 calc R . . H12B H 0.9363 -0.0895 1.0165 0.031 Uiso 1 1 calc R . . H12C H 0.7652 -0.2345 0.9909 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 O1 0.0175(4) 0.0167(4) 0.0188(4) -0.0010(3) -0.0017(3) -0.0010(3) C1 0.0236(6) 0.0185(6) 0.0120(5) -0.0009(4) 0.0029(5) 0.0012(5) O2 0.0302(5) 0.0162(4) 0.0251(4) -0.0024(3) 0.0025(4) -0.0010(4) C2 0.0186(6) 0.0199(6) 0.0164(5) -0.0010(4) 0.0004(4) 0.0029(5) C3 0.0156(5) 0.0168(6) 0.0175(5) 0.0005(4) -0.0005(4) -0.0001(5) C4 0.0201(6) 0.0128(5) 0.0174(6) -0.0024(4) -0.0005(4) -0.0044(5) C5 0.0198(5) 0.0153(5) 0.0202(5) -0.0018(4) -0.0027(5) -0.0002(4) C6 0.0300(6) 0.0170(5) 0.0170(5) -0.0002(5) -0.0058(5) -0.0039(5) C7 0.0292(6) 0.0167(5) 0.0167(5) -0.0026(5) 0.0044(5) -0.0053(5) C8 0.0206(6) 0.0160(5) 0.0236(6) -0.0035(4) 0.0027(5) -0.0026(4) C9 0.0188(6) 0.0130(5) 0.0193(6) -0.0019(4) -0.0015(5) -0.0027(4) C10 0.0180(5) 0.0194(6) 0.0204(6) -0.0018(5) -0.0015(5) 0.0016(5) C11 0.0175(5) 0.0159(6) 0.0185(6) -0.0003(4) -0.0020(5) -0.0015(5) C12 0.0238(6) 0.0206(6) 0.0178(5) 0.0008(5) -0.0028(5) 0.0002(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 O1 C1 1.3512(15) . ? O1 C11 1.4796(14) . ? C1 O2 1.2049(15) . ? C1 C2 1.5032(17) . ? C2 C3 1.5237(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5159(15) . ? C3 C11 1.5491(15) . ? C3 H3 1.0000 . ? C4 C5 1.3882(17) . ? C4 C9 1.3935(17) . ? C5 C6 1.3910(17) . ? C5 H5 0.9500 . ? C6 C7 1.3906(18) . ? C6 H6 0.9500 . ? C7 C8 1.3947(18) . ? C7 H7 0.9500 . ? C8 C9 1.3912(17) . ? C8 H8 0.9500 . ? C9 C10 1.5120(16) . ? C10 C11 1.5263(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5134(16) . ? 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 C1 O1 C11 111.16(9) . . ? O2 C1 O1 120.73(12) . . ? O2 C1 C2 128.96(11) . . ? O1 C1 C2 110.31(10) . . ? C1 C2 C3 102.74(9) . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C4 C3 C2 114.11(9) . . ? C4 C3 C11 102.76(9) . . ? C2 C3 C11 103.14(9) . . ? C4 C3 H3 112.0 . . ? C2 C3 H3 112.0 . . ? C11 C3 H3 112.0 . . ? C5 C4 C9 120.89(11) . . ? C5 C4 C3 128.34(10) . . ? C9 C4 C3 110.75(10) . . ? C4 C5 C6 118.69(11) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 120.56(11) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.83(11) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 118.51(11) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C4 120.50(11) . . ? C8 C9 C10 129.12(10) . . ? C4 C9 C10 110.38(10) . . ? C9 C10 C11 103.79(9) . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10B 111.0 . . ? C11 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? O1 C11 C12 107.73(9) . . ? O1 C11 C10 107.38(9) . . ? C12 C11 C10 116.48(10) . . ? O1 C11 C3 102.42(9) . . ? C12 C11 C3 115.60(10) . . ? C10 C11 C3 106.07(9) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.15 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.142 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036