data_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 O2' _chemical_formula_weight 246.34 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 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 6.8519(15) _cell_length_b 13.520(3) _cell_length_c 14.696(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1361.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4048 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14303 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3240 _reflns_number_gt 2782 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0400P)^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 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 0.3(8) _refine_ls_number_reflns 3240 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _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 0.23592(11) 0.59927(5) 0.52173(5) 0.01953(18) Uani 1 1 d . . . O2 O 0.00053(12) 0.71259(6) 0.53463(6) 0.0278(2) Uani 1 1 d . . . C1 C 0.35130(15) 0.55060(8) 0.45021(7) 0.0170(2) Uani 1 1 d . . . H1 H 0.2996 0.4821 0.4411 0.020 Uiso 1 1 calc R . . C2 C 0.56001(15) 0.54365(8) 0.48106(7) 0.0176(2) Uani 1 1 d . . . H2 H 0.6521 0.5841 0.4436 0.021 Uiso 1 1 calc R . . C3 C 0.62059(18) 0.53414(9) 0.57966(7) 0.0249(3) Uani 1 1 d . . . H3A H 0.7384 0.5705 0.5996 0.030 Uiso 1 1 calc R . . H3B H 0.5160 0.5292 0.6259 0.030 Uiso 1 1 calc R . . C4 C 0.64844(17) 0.44775(8) 0.51604(7) 0.0202(2) Uani 1 1 d . . . C5 C 0.84966(17) 0.42199(8) 0.48063(8) 0.0243(3) Uani 1 1 d . . . H5A H 0.9126 0.3751 0.5232 0.029 Uiso 1 1 calc R . . H5B H 0.9303 0.4827 0.4788 0.029 Uiso 1 1 calc R . . C6 C 0.84411(18) 0.37553(9) 0.38497(8) 0.0251(3) Uani 1 1 d . . . H6A H 0.9791 0.3648 0.3631 0.030 Uiso 1 1 calc R . . H6B H 0.7781 0.3105 0.3879 0.030 Uiso 1 1 calc R . . C7 C 0.73740(17) 0.44162(9) 0.31958(7) 0.0219(2) Uani 1 1 d . . . H7 H 0.8005 0.5022 0.3052 0.026 Uiso 1 1 calc R . . C8 C 0.56629(16) 0.42655(9) 0.27911(7) 0.0220(3) Uani 1 1 d . . . C9 C 0.46782(18) 0.50977(9) 0.22772(7) 0.0256(3) Uani 1 1 d . . . H9A H 0.4321 0.4856 0.1664 0.031 Uiso 1 1 calc R . . H9B H 0.5628 0.5643 0.2198 0.031 Uiso 1 1 calc R . . C10 C 0.28405(16) 0.55120(9) 0.27371(7) 0.0222(2) Uani 1 1 d . . . H10A H 0.1960 0.4952 0.2878 0.027 Uiso 1 1 calc R . . H10B H 0.2157 0.5942 0.2294 0.027 Uiso 1 1 calc R . . C11 C 0.31616(16) 0.61094(8) 0.36180(7) 0.0169(2) Uani 1 1 d . . . H11 H 0.4305 0.6558 0.3524 0.020 Uiso 1 1 calc R . . C12 C 0.14181(17) 0.67368(8) 0.38685(8) 0.0187(2) Uani 1 1 d . . . C13 C 0.11344(16) 0.66776(8) 0.48662(8) 0.0199(2) Uani 1 1 d . . . C14 C 0.02217(18) 0.72641(9) 0.33570(8) 0.0308(3) Uani 1 1 d . . . H14A H -0.0835 0.7611 0.3628 0.037 Uiso 1 1 calc R . . H14B H 0.0418 0.7297 0.2718 0.037 Uiso 1 1 calc R . . C15 C 0.51605(18) 0.35974(9) 0.53181(9) 0.0295(3) Uani 1 1 d . . . H15A H 0.5783 0.3140 0.5746 0.044 Uiso 1 1 calc R . . H15B H 0.4926 0.3258 0.4739 0.044 Uiso 1 1 calc R . . H15C H 0.3915 0.3825 0.5571 0.044 Uiso 1 1 calc R . . C16 C 0.45539(19) 0.33033(9) 0.27937(9) 0.0311(3) Uani 1 1 d . . . H16A H 0.5339 0.2792 0.3092 0.047 Uiso 1 1 calc R . . H16B H 0.4277 0.3103 0.2166 0.047 Uiso 1 1 calc R . . H16C H 0.3324 0.3389 0.3125 0.047 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 0.0204(4) 0.0222(4) 0.0160(4) -0.0003(3) 0.0031(3) 0.0017(3) O2 0.0290(5) 0.0281(5) 0.0264(4) -0.0042(4) 0.0066(4) 0.0068(4) C1 0.0195(5) 0.0150(5) 0.0164(5) -0.0025(4) 0.0019(4) 0.0001(5) C2 0.0204(6) 0.0167(5) 0.0157(5) -0.0002(4) -0.0010(5) -0.0011(4) C3 0.0271(7) 0.0289(6) 0.0187(6) -0.0015(5) -0.0053(5) 0.0038(5) C4 0.0221(6) 0.0187(5) 0.0200(5) 0.0023(5) -0.0015(5) 0.0015(5) C5 0.0231(6) 0.0218(5) 0.0282(6) 0.0001(5) -0.0035(5) 0.0034(5) C6 0.0200(6) 0.0240(6) 0.0313(6) -0.0036(5) 0.0027(5) 0.0029(5) C7 0.0219(6) 0.0223(5) 0.0216(6) -0.0017(5) 0.0076(5) -0.0001(5) C8 0.0245(6) 0.0246(6) 0.0170(5) -0.0056(5) 0.0059(5) 0.0039(5) C9 0.0300(7) 0.0324(6) 0.0145(5) -0.0045(5) 0.0021(5) 0.0041(5) C10 0.0233(6) 0.0273(6) 0.0159(5) -0.0033(5) -0.0030(5) 0.0041(5) C11 0.0167(6) 0.0192(5) 0.0147(5) -0.0011(4) -0.0009(4) -0.0009(4) C12 0.0196(6) 0.0178(5) 0.0188(5) -0.0027(4) 0.0009(5) -0.0010(5) C13 0.0207(6) 0.0164(5) 0.0225(5) -0.0013(5) 0.0005(5) -0.0016(4) C14 0.0350(7) 0.0316(7) 0.0258(6) -0.0004(6) -0.0007(6) 0.0115(6) C15 0.0309(7) 0.0238(6) 0.0338(7) 0.0073(5) 0.0050(6) 0.0004(5) C16 0.0299(7) 0.0287(6) 0.0346(7) -0.0103(6) -0.0026(6) 0.0004(6) _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 C13 1.3520(13) . ? O1 C1 1.4706(12) . ? O2 C13 1.2098(13) . ? C1 C2 1.5031(15) . ? C1 C11 1.5530(14) . ? C1 H1 1.0000 . ? C2 C3 1.5129(15) . ? C2 C4 1.5206(15) . ? C2 H2 1.0000 . ? C3 C4 1.5082(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C15 1.5141(17) . ? C4 C5 1.5143(17) . ? C5 C6 1.5402(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5022(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.3303(16) . ? C7 H7 0.9500 . ? C8 C16 1.5066(17) . ? C8 C9 1.5138(16) . ? C9 C10 1.5350(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5417(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5107(16) . ? C11 H11 1.0000 . ? C12 C14 1.3211(16) . ? C12 C13 1.4813(16) . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C13 O1 C1 111.55(8) . . ? O1 C1 C2 108.90(8) . . ? O1 C1 C11 106.24(8) . . ? C2 C1 C11 115.64(9) . . ? O1 C1 H1 108.6 . . ? C2 C1 H1 108.6 . . ? C11 C1 H1 108.6 . . ? C1 C2 C3 123.73(9) . . ? C1 C2 C4 122.30(9) . . ? C3 C2 C4 59.63(7) . . ? C1 C2 H2 113.6 . . ? C3 C2 H2 113.6 . . ? C4 C2 H2 113.6 . . ? C4 C3 C2 60.44(7) . . ? C4 C3 H3A 117.7 . . ? C2 C3 H3A 117.7 . . ? C4 C3 H3B 117.7 . . ? C2 C3 H3B 117.7 . . ? H3A C3 H3B 114.8 . . ? C3 C4 C15 115.97(10) . . ? C3 C4 C5 120.42(10) . . ? C15 C4 C5 114.67(10) . . ? C3 C4 C2 59.93(7) . . ? C15 C4 C2 118.89(10) . . ? C5 C4 C2 116.27(10) . . ? C4 C5 C6 112.64(10) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 110.70(9) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 128.60(11) . . ? C8 C7 H7 115.7 . . ? C6 C7 H7 115.7 . . ? C7 C8 C16 125.14(12) . . ? C7 C8 C9 120.14(11) . . ? C16 C8 C9 114.72(11) . . ? C8 C9 C10 114.65(10) . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 116.35(10) . . ? C9 C10 H10A 108.2 . . ? C11 C10 H10A 108.2 . . ? C9 C10 H10B 108.2 . . ? C11 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? C12 C11 C10 112.70(9) . . ? C12 C11 C1 102.34(8) . . ? C10 C11 C1 116.72(9) . . ? C12 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C1 C11 H11 108.2 . . ? C14 C12 C13 120.73(11) . . ? C14 C12 C11 130.92(11) . . ? C13 C12 C11 108.34(9) . . ? O2 C13 O1 121.16(11) . . ? O2 C13 C12 129.36(11) . . ? O1 C13 C12 109.47(9) . . ? C12 C14 H14A 120.0 . . ? C12 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C4 C15 H15A 109.5 . . ? C4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C13 O1 C1 C2 135.67(9) . . . . ? C13 O1 C1 C11 10.50(11) . . . . ? O1 C1 C2 C3 30.37(14) . . . . ? C11 C1 C2 C3 149.85(10) . . . . ? O1 C1 C2 C4 103.08(11) . . . . ? C11 C1 C2 C4 -137.44(10) . . . . ? C1 C2 C3 C4 110.70(12) . . . . ? C2 C3 C4 C15 -109.81(11) . . . . ? C2 C3 C4 C5 104.67(11) . . . . ? C1 C2 C4 C3 -113.01(12) . . . . ? C1 C2 C4 C15 -8.03(16) . . . . ? C3 C2 C4 C15 104.98(12) . . . . ? C1 C2 C4 C5 135.48(10) . . . . ? C3 C2 C4 C5 -111.51(11) . . . . ? C3 C4 C5 C6 -149.20(10) . . . . ? C15 C4 C5 C6 64.86(13) . . . . ? C2 C4 C5 C6 -80.18(12) . . . . ? C4 C5 C6 C7 54.92(13) . . . . ? C5 C6 C7 C8 -111.82(13) . . . . ? C6 C7 C8 C16 -10.28(19) . . . . ? C6 C7 C8 C9 169.70(11) . . . . ? C7 C8 C9 C10 -109.38(12) . . . . ? C16 C8 C9 C10 70.60(13) . . . . ? C8 C9 C10 C11 70.01(14) . . . . ? C9 C10 C11 C12 162.78(10) . . . . ? C9 C10 C11 C1 -79.20(13) . . . . ? O1 C1 C11 C12 -13.96(10) . . . . ? C2 C1 C11 C12 -134.88(9) . . . . ? O1 C1 C11 C10 -137.48(9) . . . . ? C2 C1 C11 C10 101.59(11) . . . . ? C10 C11 C12 C14 -39.68(17) . . . . ? C1 C11 C12 C14 -165.86(12) . . . . ? C10 C11 C12 C13 139.20(10) . . . . ? C1 C11 C12 C13 13.02(11) . . . . ? C1 O1 C13 O2 176.80(10) . . . . ? C1 O1 C13 C12 -2.10(11) . . . . ? C14 C12 C13 O2 -7.26(19) . . . . ? C11 C12 C13 O2 173.73(11) . . . . ? C14 C12 C13 O1 171.52(10) . . . . ? C11 C12 C13 O1 -7.49(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.145 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.038