data_joef103 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 O2' _chemical_formula_weight 240.29 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.487(5) _cell_length_b 6.052(3) _cell_length_c 36.080(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.484(12) _cell_angle_gamma 90.00 _cell_volume 2492.1(16) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 991 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.95 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 11114 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2197 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.1769P)^2^+7.9447P] 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 2197 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.2747 _refine_ls_wR_factor_gt 0.2671 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.8288(3) 1.1285(6) 0.54324(11) 0.0390(9) Uani 1 1 d . . . H1A H 0.8245 1.0692 0.5175 0.047 Uiso 1 1 calc R . . H1B H 0.7488 1.1734 0.5479 0.047 Uiso 1 1 calc R . . C2 C 0.9078(3) 1.3266(7) 0.54660(11) 0.0419(9) Uani 1 1 d . . . H2A H 0.9112 1.3873 0.5722 0.050 Uiso 1 1 calc R . . H2B H 0.8752 1.4423 0.5290 0.050 Uiso 1 1 calc R . . C3 C 1.0314(3) 1.2666(7) 0.53821(11) 0.0426(10) Uani 1 1 d . . . H3A H 1.0318 1.2483 0.5110 0.051 Uiso 1 1 calc R . . H3B H 1.0858 1.3883 0.5465 0.051 Uiso 1 1 calc R . . C4 C 1.0724(3) 1.0583(7) 0.55752(11) 0.0384(9) Uani 1 1 d . . . H4A H 1.1538 1.0263 0.5595 0.046 Uiso 1 1 calc R . . C5 C 1.0036(3) 0.9155(6) 0.57197(11) 0.0377(9) Uani 1 1 d . . . H5A H 1.0379 0.7865 0.5836 0.045 Uiso 1 1 calc R . . C6 C 0.8728(3) 0.9469(6) 0.57103(10) 0.0330(8) Uani 1 1 d . . . H6A H 0.8340 0.8053 0.5624 0.040 Uiso 1 1 calc R . . C7 C 0.8445(3) 0.9908(6) 0.61074(10) 0.0345(9) Uani 1 1 d . . . H7A H 0.8919 1.1185 0.6217 0.041 Uiso 1 1 calc R . . C8 C 0.8629(3) 0.7946(6) 0.63591(10) 0.0324(8) Uani 1 1 d . . . H8A H 0.9360 0.7221 0.6418 0.039 Uiso 1 1 calc R . . C9 C 0.7641(3) 0.7344(6) 0.64900(9) 0.0294(8) Uani 1 1 d . . . C10 C 0.6725(3) 0.8928(6) 0.63316(9) 0.0305(8) Uani 1 1 d . . . C11 C 0.8356(3) 0.4049(6) 0.68636(10) 0.0361(9) Uani 1 1 d . . . H11A H 0.9114 0.4309 0.6791 0.043 Uiso 1 1 calc R . . C12 C 0.8181(4) 0.2277(7) 0.70891(11) 0.0430(10) Uani 1 1 d . . . H12A H 0.8816 0.1322 0.7170 0.052 Uiso 1 1 calc R . . C13 C 0.7082(4) 0.1877(7) 0.71999(11) 0.0446(10) Uani 1 1 d . . . H13A H 0.6959 0.0652 0.7355 0.053 Uiso 1 1 calc R . . C14 C 0.6170(3) 0.3288(7) 0.70805(11) 0.0426(10) Uani 1 1 d . . . H14A H 0.5415 0.3021 0.7155 0.051 Uiso 1 1 calc R . . C15 C 0.6336(3) 0.5075(7) 0.68555(10) 0.0379(9) Uani 1 1 d . . . H15A H 0.5699 0.6036 0.6780 0.045 Uiso 1 1 calc R . . C16 C 0.7434(3) 0.5482(6) 0.67378(9) 0.0293(8) Uani 1 1 d . . . O1 O 0.72053(19) 1.0375(4) 0.61065(7) 0.0355(7) Uani 1 1 d . . . O2 O 0.57018(19) 0.9070(4) 0.63771(7) 0.0393(7) Uani 1 1 d . . . 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 C1 0.0285(18) 0.039(2) 0.050(2) 0.0056(17) 0.0067(14) 0.0036(15) C2 0.041(2) 0.032(2) 0.053(2) 0.0080(17) 0.0080(16) 0.0025(16) C3 0.035(2) 0.040(2) 0.054(2) 0.0050(18) 0.0111(16) -0.0098(17) C4 0.0235(17) 0.041(2) 0.053(2) -0.0005(17) 0.0120(15) 0.0016(15) C5 0.0267(18) 0.032(2) 0.056(2) 0.0066(16) 0.0104(15) 0.0091(15) C6 0.0242(17) 0.0257(18) 0.050(2) 0.0040(15) 0.0072(14) 0.0040(13) C7 0.0190(16) 0.034(2) 0.051(2) 0.0039(16) 0.0062(14) 0.0059(13) C8 0.0215(15) 0.0308(19) 0.0454(19) 0.0055(15) 0.0050(13) 0.0076(14) C9 0.0226(15) 0.0301(19) 0.0359(17) -0.0014(14) 0.0052(12) 0.0062(13) C10 0.0238(17) 0.0282(18) 0.0402(18) 0.0027(14) 0.0070(13) 0.0067(13) C11 0.0326(18) 0.032(2) 0.0465(19) 0.0046(16) 0.0148(15) 0.0122(15) C12 0.049(2) 0.035(2) 0.047(2) 0.0053(17) 0.0134(16) 0.0176(18) C13 0.055(2) 0.038(2) 0.042(2) 0.0026(17) 0.0107(17) -0.0038(19) C14 0.0336(19) 0.046(2) 0.049(2) 0.0040(18) 0.0085(16) -0.0075(17) C15 0.0242(17) 0.043(2) 0.047(2) 0.0036(17) 0.0057(14) 0.0002(15) C16 0.0265(16) 0.0276(18) 0.0339(16) 0.0001(14) 0.0048(13) 0.0047(13) O1 0.0227(12) 0.0323(14) 0.0531(15) 0.0099(11) 0.0107(10) 0.0109(10) O2 0.0203(12) 0.0410(16) 0.0582(16) 0.0073(12) 0.0117(10) 0.0111(10) _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 C1 C2 1.500(6) . ? C1 C6 1.534(5) . ? C2 C3 1.529(5) . ? C3 C4 1.491(6) . ? C4 C5 1.318(5) . ? C5 C6 1.510(4) . ? C6 C7 1.528(5) . ? C7 O1 1.452(4) . ? C7 C8 1.495(5) . ? C8 C9 1.330(5) . ? C9 C16 1.474(5) . ? C9 C10 1.489(4) . ? C10 O2 1.208(4) . ? C10 O1 1.353(4) . ? C11 C12 1.374(5) . ? C11 C16 1.404(5) . ? C12 C13 1.388(6) . ? C13 C14 1.383(6) . ? C14 C15 1.378(6) . ? C15 C16 1.397(5) . ? 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 C2 C1 C6 111.6(3) . . ? C1 C2 C3 111.1(3) . . ? C4 C3 C2 111.1(3) . . ? C5 C4 C3 124.6(3) . . ? C4 C5 C6 123.2(3) . . ? C5 C6 C7 108.5(3) . . ? C5 C6 C1 111.0(3) . . ? C7 C6 C1 113.5(3) . . ? O1 C7 C8 103.1(3) . . ? O1 C7 C6 110.1(3) . . ? C8 C7 C6 113.6(3) . . ? C9 C8 C7 111.4(3) . . ? C8 C9 C16 128.9(3) . . ? C8 C9 C10 106.4(3) . . ? C16 C9 C10 124.7(3) . . ? O2 C10 O1 120.3(3) . . ? O2 C10 C9 130.5(3) . . ? O1 C10 C9 109.2(3) . . ? C12 C11 C16 121.2(3) . . ? C11 C12 C13 120.3(4) . . ? C14 C13 C12 119.0(4) . . ? C15 C14 C13 121.2(4) . . ? C14 C15 C16 120.5(3) . . ? C15 C16 C11 117.8(3) . . ? C15 C16 C9 122.1(3) . . ? C11 C16 C9 120.0(3) . . ? C10 O1 C7 109.8(3) . . ? 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 C6 C1 C2 C3 61.2(4) . . . . ? C1 C2 C3 C4 -45.3(4) . . . . ? C2 C3 C4 C5 15.9(6) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C4 C5 C6 C7 -111.0(4) . . . . ? C4 C5 C6 C1 14.4(5) . . . . ? C2 C1 C6 C5 -44.1(4) . . . . ? C2 C1 C6 C7 78.4(4) . . . . ? C5 C6 C7 O1 176.0(3) . . . . ? C1 C6 C7 O1 52.1(4) . . . . ? C5 C6 C7 C8 -68.9(4) . . . . ? C1 C6 C7 C8 167.2(3) . . . . ? O1 C7 C8 C9 -0.3(4) . . . . ? C6 C7 C8 C9 -119.5(3) . . . . ? C7 C8 C9 C16 178.5(3) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 O2 -178.3(4) . . . . ? C16 C9 C10 O2 2.5(6) . . . . ? C8 C9 C10 O1 1.3(4) . . . . ? C16 C9 C10 O1 -177.8(3) . . . . ? C16 C11 C12 C13 -0.5(6) . . . . ? C11 C12 C13 C14 -0.1(6) . . . . ? C12 C13 C14 C15 -0.2(6) . . . . ? C13 C14 C15 C16 1.0(6) . . . . ? C14 C15 C16 C11 -1.5(5) . . . . ? C14 C15 C16 C9 178.5(3) . . . . ? C12 C11 C16 C15 1.2(5) . . . . ? C12 C11 C16 C9 -178.8(3) . . . . ? C8 C9 C16 C15 179.3(4) . . . . ? C10 C9 C16 C15 -1.8(5) . . . . ? C8 C9 C16 C11 -0.7(6) . . . . ? C10 C9 C16 C11 178.3(3) . . . . ? O2 C10 O1 C7 178.1(3) . . . . ? C9 C10 O1 C7 -1.5(4) . . . . ? C8 C7 O1 C10 1.1(4) . . . . ? C6 C7 O1 C10 122.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.472 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.074