data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 O2' _chemical_formula_weight 272.37 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.849(2) _cell_length_b 8.040(3) _cell_length_c 8.248(4) _cell_angle_alpha 70.981(9) _cell_angle_beta 67.810(10) _cell_angle_gamma 68.179(12) _cell_volume 381.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 3235 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prisms _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 148 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? # 1 deg scans, 100 seconds per frame # _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCX-Mini with Mercury CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3260 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1329 _reflns_number_gt 1166 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0429P)^2^+0.1499P] 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_number_reflns 1329 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.1734 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 1.559 _refine_ls_restrained_S_all 1.559 _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 0.7570(3) 0.6060(2) 0.6535(2) 0.0380(5) Uani 1 1 d . . . C1 C 0.4456(3) 0.5074(3) 0.4389(3) 0.0296(5) Uani 1 1 d . . . C2 C 0.4415(4) 0.6585(3) 0.2868(3) 0.0341(6) Uani 1 1 d . . . H2 H 0.3695 0.6695 0.2052 0.041 Uiso 1 1 calc R . . C3 C 0.5419(4) 0.7851(3) 0.2619(3) 0.0354(6) Uani 1 1 d . . . H3 H 0.5395 0.8833 0.1615 0.042 Uiso 1 1 calc R . . C4 C 0.6506(4) 0.7741(3) 0.3826(3) 0.0360(6) Uani 1 1 d . . . H4 H 0.7179 0.8646 0.3626 0.043 Uiso 1 1 calc R . . C5 C 0.6571(3) 0.6303(3) 0.5290(3) 0.0316(5) Uani 1 1 d . . . C6 C 0.8590(4) 0.7418(3) 0.6299(3) 0.0340(6) Uani 1 1 d . . . H6A H 0.7504 0.8627 0.6287 0.041 Uiso 1 1 calc R . . H6B H 0.9758 0.7473 0.5155 0.041 Uiso 1 1 calc R . . C7 C 0.9541(4) 0.6899(3) 0.7832(3) 0.0347(6) Uani 1 1 d . . . H7A H 1.0619 0.5686 0.7832 0.042 Uiso 1 1 calc R . . H7B H 0.8364 0.6821 0.8968 0.042 Uiso 1 1 calc R . . C8 C 1.0646(4) 0.8287(3) 0.7697(3) 0.0404(6) Uani 1 1 d . . . H8A H 0.9545 0.9484 0.7757 0.049 Uiso 1 1 calc R . . H8B H 1.1763 0.8414 0.6529 0.049 Uiso 1 1 calc R . . C9 C 1.1728(4) 0.7750(4) 0.9171(3) 0.0446(6) Uani 1 1 d . . . H9A H 1.0622 0.7669 1.0330 0.067 Uiso 1 1 calc R . . H9B H 1.2423 0.8670 0.9009 0.067 Uiso 1 1 calc R . . H9C H 1.2828 0.6570 0.9114 0.067 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 0.0451(10) 0.0410(9) 0.0361(9) -0.0031(7) -0.0190(7) -0.0182(7) C1 0.0292(11) 0.0300(11) 0.0270(11) -0.0068(9) -0.0087(9) -0.0046(9) C2 0.0346(12) 0.0385(13) 0.0296(12) -0.0082(9) -0.0128(9) -0.0067(10) C3 0.0389(12) 0.0337(12) 0.0291(11) -0.0029(9) -0.0109(9) -0.0081(10) C4 0.0401(13) 0.0328(12) 0.0371(13) -0.0040(10) -0.0123(10) -0.0146(10) C5 0.0311(11) 0.0355(12) 0.0288(11) -0.0080(9) -0.0104(9) -0.0075(9) C6 0.0358(12) 0.0324(12) 0.0347(12) -0.0073(9) -0.0109(10) -0.0100(9) C7 0.0380(12) 0.0373(12) 0.0294(12) -0.0090(9) -0.0080(9) -0.0117(10) C8 0.0464(14) 0.0368(13) 0.0420(14) -0.0051(10) -0.0179(11) -0.0139(11) C9 0.0530(15) 0.0445(14) 0.0453(14) -0.0079(11) -0.0213(12) -0.0180(12) _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 C5 1.365(3) . ? O1 C6 1.429(3) . ? C1 C1 1.418(4) 2_666 ? C1 C5 1.427(3) 2_666 ? C1 C2 1.434(3) . ? C2 C3 1.352(3) . ? C2 H2 0.9400 . ? C3 C4 1.417(3) . ? C3 H3 0.9400 . ? C4 C5 1.374(3) . ? C4 H4 0.9400 . ? C5 C1 1.427(3) 2_666 ? C6 C7 1.508(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.521(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.522(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? 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 C5 O1 C6 117.16(17) . . ? C1 C1 C5 118.6(2) 2_666 2_666 ? C1 C1 C2 119.7(2) 2_666 . ? C5 C1 C2 121.72(19) 2_666 . ? C3 C2 C1 119.5(2) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.9(2) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? O1 C5 C4 124.6(2) . . ? O1 C5 C1 114.74(18) . 2_666 ? C4 C5 C1 120.7(2) . 2_666 ? O1 C6 C7 108.12(18) . . ? O1 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? O1 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? C6 C7 C8 111.68(19) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 112.98(19) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C1 C1 C2 C3 0.1(4) 2_666 . . . ? C5 C1 C2 C3 -179.8(2) 2_666 . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C6 O1 C5 C4 0.8(3) . . . . ? C6 O1 C5 C1 -178.85(17) . . . 2_666 ? C3 C4 C5 O1 179.96(19) . . . . ? C3 C4 C5 C1 -0.4(3) . . . 2_666 ? C5 O1 C6 C7 178.90(17) . . . . ? O1 C6 C7 C8 -179.45(17) . . . . ? C6 C7 C8 C9 -176.97(19) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.518 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.066