data_C13H22O2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H22 O2' _chemical_formula_sum 'C13 H22 O2' _chemical_formula_weight 210.31 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 7.9329(3) _cell_length_b 7.1935(3) _cell_length_c 10.3786(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.3910(10) _cell_angle_gamma 90.00 _cell_volume 592.24(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5139 _cell_measurement_theta_min 7.00 _cell_measurement_theta_max 67.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method none _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.605 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9094 _exptl_absorpt_correction_T_max 0.9646 _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 5618 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 67.51 _reflns_number_total 2067 _reflns_number_gt 2042 _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^)+(0.0451P)^2^+0.0907P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef na _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.18(18) _refine_ls_number_reflns 2067 _refine_ls_number_parameters 142 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.049 _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 0.52288(13) 0.49492(14) 0.36381(9) 0.0270(2) Uani 1 1 d D . . H1O H 0.512(2) 0.385(2) 0.3568(19) 0.040 Uiso 1 1 d D . . O2 O 0.46856(12) 1.12581(13) 0.38849(9) 0.0257(2) Uani 1 1 d D . . H2O H 0.467(2) 1.088(3) 0.4619(14) 0.039 Uiso 1 1 d D . . C1 C 0.52383(15) 0.57662(17) 0.23767(12) 0.0187(3) Uani 1 1 d . . . H1 H 0.5343 0.4754 0.1722 0.022 Uiso 1 1 calc R . . C2 C 0.35741(16) 0.67902(19) 0.21528(12) 0.0219(3) Uani 1 1 d . . . H2A H 0.2626 0.5920 0.2291 0.026 Uiso 1 1 calc R . . H2B H 0.3518 0.7225 0.1249 0.026 Uiso 1 1 calc R . . C3 C 0.33878(16) 0.84558(18) 0.30564(13) 0.0235(3) Uani 1 1 d . . . H3A H 0.2364 0.9164 0.2812 0.028 Uiso 1 1 calc R . . H3B H 0.3241 0.8003 0.3949 0.028 Uiso 1 1 calc R . . C4 C 0.49095(16) 0.97423(17) 0.30096(12) 0.0195(3) Uani 1 1 d . . . H4 H 0.4973 1.0269 0.2120 0.023 Uiso 1 1 calc R . . C5 C 0.65614(16) 0.86758(17) 0.32734(12) 0.0185(3) Uani 1 1 d . . . H5 H 0.6452 0.8082 0.4140 0.022 Uiso 1 1 calc R . . C6 C 0.67866(15) 0.70716(16) 0.22712(12) 0.0166(3) Uani 1 1 d . . . C7 C 0.80372(16) 0.99885(19) 0.33477(12) 0.0247(3) Uani 1 1 d . . . H7A H 0.8354 1.0615 0.2581 0.030 Uiso 1 1 calc R . . C8 C 0.89211(18) 1.0330(2) 0.44014(15) 0.0321(3) Uani 1 1 d . . . H8A H 0.8641 0.9729 0.5186 0.038 Uiso 1 1 calc R . . H8C H 0.9839 1.1178 0.4376 0.038 Uiso 1 1 calc R . . C9 C 0.69449(15) 0.78593(17) 0.08891(11) 0.0179(3) Uani 1 1 d . . . H9A H 0.5863 0.8450 0.0642 0.021 Uiso 1 1 calc R . . H9B H 0.7822 0.8839 0.0890 0.021 Uiso 1 1 calc R . . C10 C 0.73931(16) 0.64047(18) -0.01236(12) 0.0219(3) Uani 1 1 d . . . H10A H 0.6447 0.5517 -0.0217 0.026 Uiso 1 1 calc R . . H10C H 0.7555 0.7026 -0.0965 0.026 Uiso 1 1 calc R . . C11 C 0.89913(17) 0.5343(2) 0.02364(14) 0.0267(3) Uani 1 1 d . . . H11A H 0.9188 0.4344 -0.0401 0.032 Uiso 1 1 calc R . . H11B H 0.9969 0.6197 0.0217 0.032 Uiso 1 1 calc R . . C12 C 0.88354(16) 0.44979(18) 0.15751(14) 0.0259(3) Uani 1 1 d . . . H12A H 0.9910 0.3884 0.1814 0.031 Uiso 1 1 calc R . . H12B H 0.7940 0.3539 0.1565 0.031 Uiso 1 1 calc R . . C13 C 0.84125(16) 0.59799(18) 0.25832(13) 0.0232(3) Uani 1 1 d . . . H13A H 0.9365 0.6865 0.2649 0.028 Uiso 1 1 calc R . . H13B H 0.8288 0.5371 0.3433 0.028 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 0.0439(6) 0.0164(5) 0.0206(4) 0.0025(4) 0.0038(4) -0.0056(4) O2 0.0404(5) 0.0160(5) 0.0207(4) -0.0023(4) 0.0028(4) 0.0035(4) C1 0.0227(6) 0.0153(6) 0.0182(6) -0.0005(5) 0.0019(4) -0.0029(5) C2 0.0177(6) 0.0225(7) 0.0253(6) -0.0033(5) 0.0024(5) -0.0040(5) C3 0.0212(6) 0.0229(7) 0.0265(7) -0.0012(5) 0.0042(5) 0.0017(5) C4 0.0268(6) 0.0142(6) 0.0175(6) -0.0016(5) 0.0016(5) 0.0019(5) C5 0.0238(6) 0.0140(6) 0.0178(6) 0.0003(5) -0.0013(4) -0.0019(5) C6 0.0180(6) 0.0132(6) 0.0185(6) -0.0007(5) -0.0011(4) -0.0003(5) C7 0.0284(7) 0.0182(6) 0.0275(6) -0.0006(5) 0.0008(5) -0.0048(6) C8 0.0296(7) 0.0284(8) 0.0381(7) -0.0072(6) -0.0059(6) -0.0053(6) C9 0.0171(6) 0.0163(6) 0.0203(6) 0.0004(5) 0.0017(4) -0.0004(4) C10 0.0238(6) 0.0204(6) 0.0215(6) -0.0011(5) 0.0044(5) -0.0030(5) C11 0.0219(6) 0.0208(7) 0.0375(7) -0.0068(6) 0.0069(5) 0.0001(5) C12 0.0220(6) 0.0172(6) 0.0384(7) -0.0037(5) -0.0021(5) 0.0043(5) C13 0.0223(6) 0.0190(7) 0.0283(6) -0.0008(5) -0.0059(5) 0.0017(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 1.4351(15) . ? O1 H1O 0.796(16) . ? O2 C4 1.4311(15) . ? O2 H2O 0.809(14) . ? C1 C2 1.5282(17) . ? C1 C6 1.5505(15) . ? C1 H1 1.0000 . ? C2 C3 1.5293(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5221(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5414(17) . ? C4 H4 1.0000 . ? C5 C7 1.5056(17) . ? C5 C6 1.5646(16) . ? C5 H5 1.0000 . ? C6 C13 1.5426(16) . ? C6 C9 1.5482(16) . ? C7 C8 1.318(2) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C8 H8C 0.9500 . ? C9 C10 1.5267(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5245(18) . ? C10 H10A 0.9900 . ? C10 H10C 0.9900 . ? C11 C12 1.522(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5325(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? 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 108.9(14) . . ? C4 O2 H2O 110.0(14) . . ? O1 C1 C2 109.04(10) . . ? O1 C1 C6 108.76(9) . . ? C2 C1 C6 112.41(10) . . ? O1 C1 H1 108.9 . . ? C2 C1 H1 108.9 . . ? C6 C1 H1 108.9 . . ? C1 C2 C3 111.80(10) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 112.14(10) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O2 C4 C3 109.95(10) . . ? O2 C4 C5 112.06(10) . . ? C3 C4 C5 111.42(10) . . ? O2 C4 H4 107.7 . . ? C3 C4 H4 107.7 . . ? C5 C4 H4 107.7 . . ? C7 C5 C4 110.90(10) . . ? C7 C5 C6 113.85(10) . . ? C4 C5 C6 110.48(10) . . ? C7 C5 H5 107.1 . . ? C4 C5 H5 107.1 . . ? C6 C5 H5 107.1 . . ? C13 C6 C9 107.93(9) . . ? C13 C6 C1 109.78(10) . . ? C9 C6 C1 110.88(9) . . ? C13 C6 C5 109.57(9) . . ? C9 C6 C5 110.87(10) . . ? C1 C6 C5 107.79(9) . . ? C8 C7 C5 124.65(13) . . ? C8 C7 H7A 117.7 . . ? C5 C7 H7A 117.7 . . ? C7 C8 H8A 120.0 . . ? C7 C8 H8C 120.0 . . ? H8A C8 H8C 120.0 . . ? C10 C9 C6 114.06(10) . . ? C10 C9 H9A 108.7 . . ? C6 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C6 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 111.84(10) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10C 109.2 . . ? C9 C10 H10C 109.2 . . ? H10A C10 H10C 107.9 . . ? C12 C11 C10 110.55(10) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.41(11) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C6 113.41(10) . . ? C12 C13 H13A 108.9 . . ? C6 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C6 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? 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 C3 65.73(13) . . . . ? C6 C1 C2 C3 -54.96(13) . . . . ? C1 C2 C3 C4 52.25(14) . . . . ? C2 C3 C4 O2 -179.07(10) . . . . ? C2 C3 C4 C5 -54.21(14) . . . . ? O2 C4 C5 C7 -51.03(14) . . . . ? C3 C4 C5 C7 -174.69(10) . . . . ? O2 C4 C5 C6 -178.23(10) . . . . ? C3 C4 C5 C6 58.10(13) . . . . ? O1 C1 C6 C13 55.92(12) . . . . ? C2 C1 C6 C13 176.77(10) . . . . ? O1 C1 C6 C9 175.09(10) . . . . ? C2 C1 C6 C9 -64.06(13) . . . . ? O1 C1 C6 C5 -63.38(12) . . . . ? C2 C1 C6 C5 57.47(12) . . . . ? C7 C5 C6 C13 56.50(13) . . . . ? C4 C5 C6 C13 -177.95(10) . . . . ? C7 C5 C6 C9 -62.54(13) . . . . ? C4 C5 C6 C9 63.02(12) . . . . ? C7 C5 C6 C1 175.92(10) . . . . ? C4 C5 C6 C1 -58.52(12) . . . . ? C4 C5 C7 C8 112.86(15) . . . . ? C6 C5 C7 C8 -121.81(15) . . . . ? C13 C6 C9 C10 52.55(13) . . . . ? C1 C6 C9 C10 -67.72(12) . . . . ? C5 C6 C9 C10 172.57(10) . . . . ? C6 C9 C10 C11 -54.72(14) . . . . ? C9 C10 C11 C12 54.39(14) . . . . ? C10 C11 C12 C13 -55.40(14) . . . . ? C11 C12 C13 C6 56.87(14) . . . . ? C9 C6 C13 C12 -53.46(13) . . . . ? C1 C6 C13 C12 67.51(13) . . . . ? C5 C6 C13 C12 -174.29(10) . . . . ? 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 0.796(16) 1.928(16) 2.7024(14) 164(2) 1_545 O2 H2O O1 0.809(14) 1.930(15) 2.7381(14) 176.9(19) 2_656 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 67.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.191 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.032