data_global _audit_creation_method 'APEX3 v2017.3-0' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 O2' _chemical_formula_iupac ? _chemical_formula_weight 162.18 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0807(2) _cell_length_b 12.7320(4) _cell_length_c 9.8149(3) _cell_angle_alpha 90 _cell_angle_beta 102.330(2) _cell_angle_gamma 90 _cell_volume 864.42(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7672 _cell_measurement_theta_min 3.4714 _cell_measurement_theta_max 74.8560 _cell_measurement_temperature 110.(2) _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.144 _exptl_crystal_size_mid 0.087 _exptl_crystal_size_min 0.074 _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 0.95 _exptl_special_details ; ; _diffrn_ambient_temperature 110.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10635 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_theta_min 5.78 _diffrn_reflns_theta_max 75.27 _diffrn_reflns_theta_full 75.27 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _refine_special_details ; ; _reflns_number_total 1759 _reflns_number_gt 1537 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_gt 0.1529 _refine_ls_wR_factor_ref 0.1594 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_number_reflns 1759 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1161P)^2^+0.0715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.434 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection ? _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_structure_solution 'XT, VERSION 2014/5' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 833)' _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.03427(12) 0.58693(7) 0.16863(9) 0.0249(3) Uani d . . . 1 . . O O2 0.51529(12) 0.66128(7) 0.34864(8) 0.0244(3) Uani d . . . 1 . . C C1 0.20045(17) 0.58779(9) 0.27064(12) 0.0227(3) Uani d . . . 1 . . C C2 0.18816(19) 0.51598(10) 0.37047(13) 0.0272(4) Uani d . . . 1 . . C C3 0.00291(19) 0.46700(10) 0.32781(13) 0.0293(4) Uani d . . . 1 . . C C4 -0.08523(19) 0.51206(10) 0.20615(13) 0.0256(3) Uani d . . . 1 . . C C5 -0.2768(2) 0.49849(12) 0.11097(15) 0.0327(4) Uani d . . . 1 . . C C6 0.34538(17) 0.66157(9) 0.25006(12) 0.0231(3) Uani d . . . 1 . . C C7 0.35313(19) 0.73475(10) 0.15080(13) 0.0279(4) Uani d . . . 1 . . C C8 0.53757(19) 0.78380(10) 0.19028(13) 0.0284(4) Uani d . . . 1 . . C C9 0.63182(18) 0.73734(10) 0.30938(13) 0.0252(3) Uani d . . . 1 . . C C10 0.8264(2) 0.75018(12) 0.39992(15) 0.0318(4) Uani d . . . 1 . . H H1 0.294(3) 0.5005(14) 0.4552(17) 0.037(4) Uiso d . . . 1 . . H H2 -0.055(2) 0.4104(14) 0.3786(17) 0.034(4) Uiso d . . . 1 . . H H3 -0.353(3) 0.4428(16) 0.1421(18) 0.045(5) Uiso d . . . 1 . . H H4 -0.264(3) 0.4786(16) 0.021(2) 0.055(6) Uiso d . . . 1 . . H H5 -0.356(3) 0.5661(16) 0.1103(19) 0.049(5) Uiso d . . . 1 . . H H6 0.244(3) 0.7499(16) 0.0685(19) 0.046(5) Uiso d . . . 1 . . H H7 0.598(3) 0.8384(15) 0.1411(19) 0.044(5) Uiso d . . . 1 . . H H8 0.893(3) 0.8065(17) 0.363(2) 0.057(6) Uiso d . . . 1 . . H H9 0.818(3) 0.7677(16) 0.497(2) 0.052(5) Uiso d . . . 1 . . H H10 0.900(3) 0.6831(16) 0.3967(19) 0.049(5) Uiso d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0188(5) 0.0276(5) 0.0266(5) -0.0007(3) 0.0012(4) -0.0007(3) O2 0.0197(5) 0.0268(5) 0.0251(5) -0.0018(3) 0.0012(4) -0.0009(3) C1 0.0175(6) 0.0236(6) 0.0259(6) 0.0024(5) 0.0021(5) -0.0032(4) C2 0.0234(7) 0.0273(7) 0.0296(6) 0.0029(5) 0.0031(5) 0.0011(5) C3 0.0276(7) 0.0261(7) 0.0341(6) -0.0011(5) 0.0065(5) 0.0010(5) C4 0.0214(7) 0.0246(6) 0.0312(6) -0.0023(5) 0.0065(5) -0.0054(4) C5 0.0235(7) 0.0375(8) 0.0357(7) -0.0047(6) 0.0032(6) -0.0077(5) C6 0.0186(7) 0.0239(6) 0.0258(6) 0.0022(4) 0.0023(5) -0.0030(4) C7 0.0247(7) 0.0270(6) 0.0302(6) 0.0023(5) 0.0022(5) 0.0021(5) C8 0.0268(7) 0.0251(7) 0.0330(6) -0.0019(5) 0.0054(5) 0.0009(5) C9 0.0216(7) 0.0251(6) 0.0292(6) -0.0020(5) 0.0061(5) -0.0043(4) C10 0.0233(7) 0.0359(8) 0.0344(7) -0.0059(5) 0.0019(6) -0.0041(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.3726(14) ? O1 C4 . 1.3760(15) ? O2 C6 . 1.3735(14) ? O2 C9 . 1.3794(15) ? C1 C2 . 1.3564(17) ? C1 C6 . 1.4370(18) ? C2 C3 . 1.4318(18) ? C2 H1 . 1.014(17) ? C3 C4 . 1.3514(18) ? C3 H2 . 1.012(17) ? C4 C5 . 1.4836(18) ? C5 H3 . 0.980(19) ? C5 H4 . 0.943(19) ? C5 H5 . 1.03(2) ? C6 C7 . 1.3576(17) ? C7 C8 . 1.4246(19) ? C7 H6 . 1.010(19) ? C8 C9 . 1.3523(17) ? C8 H7 . 0.994(19) ? C9 C10 . 1.4805(18) ? C10 H8 . 0.97(2) ? C10 H9 . 0.99(2) ? C10 H10 . 1.00(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 C4 . . 106.90(9) ? C6 O2 C9 . . 106.71(9) ? C2 C1 O1 . . 110.14(10) ? C2 C1 C6 . . 134.43(12) ? O1 C1 C6 . . 115.43(10) ? C1 C2 C3 . . 106.17(11) ? C1 C2 H1 . . 125.0(10) ? C3 C2 H1 . . 128.8(10) ? C4 C3 C2 . . 107.15(12) ? C4 C3 H2 . . 125.3(10) ? C2 C3 H2 . . 127.5(10) ? C3 C4 O1 . . 109.65(11) ? C3 C4 C5 . . 133.99(13) ? O1 C4 C5 . . 116.36(11) ? C4 C5 H3 . . 112.3(11) ? C4 C5 H4 . . 111.5(12) ? H3 C5 H4 . . 105.5(16) ? C4 C5 H5 . . 109.4(11) ? H3 C5 H5 . . 105.7(15) ? H4 C5 H5 . . 112.3(16) ? C7 C6 O2 . . 110.11(11) ? C7 C6 C1 . . 133.56(12) ? O2 C6 C1 . . 116.34(10) ? C6 C7 C8 . . 106.31(12) ? C6 C7 H6 . . 124.4(11) ? C8 C7 H6 . . 129.3(11) ? C9 C8 C7 . . 107.33(11) ? C9 C8 H7 . . 122.8(11) ? C7 C8 H7 . . 129.7(11) ? C8 C9 O2 . . 109.53(11) ? C8 C9 C10 . . 134.01(12) ? O2 C9 C10 . . 116.45(11) ? C9 C10 H8 . . 108.8(12) ? C9 C10 H9 . . 111.1(12) ? H8 C10 H9 . . 108.9(16) ? C9 C10 H10 . . 107.9(11) ? H8 C10 H10 . . 108.9(16) ? H9 C10 H10 . . 111.1(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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 O1 C1 C2 . . . . -0.07(13) ? C4 O1 C1 C6 . . . . 179.87(9) ? O1 C1 C2 C3 . . . . 0.20(14) ? C6 C1 C2 C3 . . . . -179.72(13) ? C1 C2 C3 C4 . . . . -0.26(15) ? C2 C3 C4 O1 . . . . 0.23(14) ? C2 C3 C4 C5 . . . . -178.76(14) ? C1 O1 C4 C3 . . . . -0.10(13) ? C1 O1 C4 C5 . . . . 179.08(10) ? C9 O2 C6 C7 . . . . 0.33(13) ? C9 O2 C6 C1 . . . . -179.75(9) ? C2 C1 C6 C7 . . . . -178.13(13) ? O1 C1 C6 C7 . . . . 1.9(2) ? C2 C1 C6 O2 . . . . 2.0(2) ? O1 C1 C6 O2 . . . . -177.96(8) ? O2 C6 C7 C8 . . . . -0.63(14) ? C1 C6 C7 C8 . . . . 179.46(13) ? C6 C7 C8 C9 . . . . 0.70(14) ? C7 C8 C9 O2 . . . . -0.51(14) ? C7 C8 C9 C10 . . . . 178.36(13) ? C6 O2 C9 C8 . . . . 0.13(13) ? C6 O2 C9 C10 . . . . -178.96(10) ?