# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/332 data_1435 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H16 O2' _chemical_formula_weight 216.27 _chemical_melting_point ? _chemical_compound_source ? 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 6.7900(10) _cell_length_b 7.614(2) _cell_length_c 12.020(2) _cell_angle_alpha 93.73(3) _cell_angle_beta 99.86(3) _cell_angle_gamma 115.41(3) _cell_volume 546.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.46 _cell_measurement_theta_max 13.84 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method ? _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type 'phi scan' _exptl_absorpt_correction_T_min 0.81594 _exptl_absorpt_correction_T_max 0.97888 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 3% _diffrn_reflns_number 1910 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1910 _reflns_number_observed 1372 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1325P)^2^+0.0600P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1910 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_obs 0.0403 _refine_ls_wR_factor_all 0.1396 _refine_ls_wR_factor_obs 0.1216 _refine_ls_goodness_of_fit_all 0.777 _refine_ls_goodness_of_fit_obs 0.815 _refine_ls_restrained_S_all 0.777 _refine_ls_restrained_S_obs 0.815 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.0133(4) 0.8059(3) -0.3791(2) 0.0492(5) Uani 1 d . . C2 C -0.2261(4) 0.6230(3) -0.3900(2) 0.0481(5) Uani 1 d . . C3 C -0.1986(3) 0.4673(3) -0.36471(14) 0.0415(5) Uani 1 d . . C4 C 0.0454(3) 0.5171(3) -0.33251(15) 0.0384(4) Uani 1 d . . C5 C 0.1220(3) 0.4856(3) -0.21351(15) 0.0379(4) Uani 1 d . . C6 C 0.3671(4) 0.5574(4) -0.1686(2) 0.0533(6) Uani 1 d . . C7 C 0.2618(3) 0.6857(3) -0.13759(15) 0.0373(4) Uani 1 d . . C8 C 0.2308(3) 0.7102(3) -0.01992(15) 0.0394(4) Uani 1 d . . O9 O 0.0980(2) 0.7948(2) -0.00517(10) 0.0478(4) Uani 1 d . . C10 C -0.0250(4) 0.8206(3) -0.1090(2) 0.0449(5) Uani 1 d . . C11 C 0.1357(4) 0.9469(3) -0.1766(2) 0.0475(5) Uani 1 d . . C12 C 0.2750(3) 0.8461(3) -0.2089(2) 0.0412(5) Uani 1 d . . C13 C 0.1684(3) 0.7421(3) -0.33466(15) 0.0421(5) Uani 1 d . . C14 C 0.0210(5) 0.9759(3) -0.2899(2) 0.0576(6) Uani 1 d . . O15 O 0.3138(3) 0.6627(2) 0.06172(12) 0.0564(4) Uani 1 d . . C16 C -0.3754(5) 0.2659(4) -0.3645(2) 0.0621(7) Uani 1 d . . H5 H 0.0225(34) 0.3764(30) -0.1846(17) 0.041(5) Uiso 1 d . . H13A H 0.4217(37) 0.9420(32) -0.2052(17) 0.045(5) Uiso 1 d . . H11 H 0.2266(38) 1.0706(35) -0.1302(20) 0.056(6) Uiso 1 d . . H10A H -0.1105(36) 0.8787(32) -0.0850(18) 0.048(5) Uiso 1 d . . H1 H -0.0008(35) 0.8508(31) -0.4496(19) 0.049(6) Uiso 1 d . . H4 H 0.0870(35) 0.4536(31) -0.3873(19) 0.045(5) Uiso 1 d . . H10B H -0.1308(31) 0.6920(29) -0.1529(16) 0.033(4) Uiso 1 d . . H14A H -0.1145(49) 0.9819(38) -0.2815(22) 0.072(8) Uiso 1 d . . H13B H 0.2876(38) 0.7785(31) -0.3780(19) 0.051(6) Uiso 1 d . . H6A H 0.4646(39) 0.6111(33) -0.2263(20) 0.061(6) Uiso 1 d . . H14B H 0.1151(43) 1.0941(40) -0.3093(21) 0.067(7) Uiso 1 d . . H6B H 0.4168(41) 0.4925(36) -0.1088(22) 0.065(7) Uiso 1 d . . H2 H -0.3655(43) 0.6261(34) -0.4076(20) 0.062(7) Uiso 1 d . . H16A H -0.3761(44) 0.2269(40) -0.2909(26) 0.077(8) Uiso 1 d . . H16B H -0.5265(64) 0.2448(52) -0.4020(32) 0.108(11) Uiso 1 d . . H16C H -0.3601(58) 0.1643(54) -0.4060(31) 0.105(11) Uiso 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 0.0701(14) 0.0448(11) 0.0348(9) 0.0138(8) 0.0074(9) 0.0282(10) C2 0.0541(12) 0.0548(12) 0.0328(9) 0.0040(8) -0.0019(8) 0.0266(10) C3 0.0495(11) 0.0432(10) 0.0242(8) 0.0020(7) 0.0029(7) 0.0162(9) C4 0.0502(11) 0.0387(10) 0.0297(8) 0.0040(7) 0.0134(8) 0.0215(8) C5 0.0477(11) 0.0366(10) 0.0353(9) 0.0061(7) 0.0117(8) 0.0234(9) C6 0.0544(13) 0.0686(14) 0.0508(12) 0.0094(10) 0.0112(10) 0.0403(12) C7 0.0331(9) 0.0393(10) 0.0376(9) 0.0053(7) 0.0057(7) 0.0154(8) C8 0.0386(10) 0.0367(9) 0.0348(9) 0.0013(7) 0.0011(7) 0.0127(8) O9 0.0575(9) 0.0549(9) 0.0324(7) -0.0030(6) 0.0059(6) 0.0292(7) C10 0.0498(12) 0.0512(12) 0.0386(10) -0.0036(9) 0.0035(9) 0.0308(10) C11 0.0575(12) 0.0284(9) 0.0480(11) -0.0010(8) -0.0005(9) 0.0166(9) C12 0.0356(10) 0.0342(10) 0.0449(10) 0.0078(8) 0.0095(8) 0.0070(8) C13 0.0489(11) 0.0421(10) 0.0357(9) 0.0117(8) 0.0159(8) 0.0175(9) C14 0.077(2) 0.0397(12) 0.0571(13) 0.0109(10) 0.0059(12) 0.0301(12) O15 0.0627(10) 0.0665(10) 0.0376(8) 0.0099(6) -0.0013(6) 0.0309(8) C16 0.063(2) 0.0527(14) 0.0451(12) 0.0062(10) 0.0015(11) 0.0062(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 C1 C2 1.493(3) . ? C1 C14 1.535(3) . ? C1 C13 1.538(3) . ? C1 H1 0.94(2) . ? C2 C3 1.323(3) . ? C2 H2 0.94(3) . ? C3 C16 1.488(3) . ? C3 C4 1.504(3) . ? C4 C5 1.507(2) . ? C4 C13 1.555(3) . ? C4 H4 0.94(2) . ? C5 C6 1.494(3) . ? C5 C7 1.529(3) . ? C5 H5 0.95(2) . ? C6 C7 1.500(3) . ? C6 H6A 1.02(2) . ? C6 H6B 0.99(2) . ? C7 C8 1.477(3) . ? C7 C12 1.517(3) . ? C8 O15 1.201(2) . ? C8 O9 1.341(2) . ? O9 C10 1.452(2) . ? C10 C11 1.510(3) . ? C10 H10A 0.94(2) . ? C10 H10B 0.98(2) . ? C11 C14 1.528(3) . ? C11 C12 1.531(3) . ? C11 H11 0.95(2) . ? C12 C13 1.554(3) . ? C12 H13A 0.94(2) . ? C13 H13B 0.99(2) . ? C14 H14A 0.96(3) . ? C14 H14B 0.93(3) . ? C16 H16A 0.95(3) . ? C16 H16B 0.99(4) . ? C16 H16C 0.95(4) . ? 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 C14 114.7(2) . . ? C2 C1 C13 103.5(2) . . ? C14 C1 C13 106.3(2) . . ? C2 C1 H1 111.2(13) . . ? C14 C1 H1 108.7(13) . . ? C13 C1 H1 112.3(13) . . ? C3 C2 C1 114.3(2) . . ? C3 C2 H2 124.8(14) . . ? C1 C2 H2 120.7(14) . . ? C2 C3 C16 127.5(2) . . ? C2 C3 C4 111.0(2) . . ? C16 C3 C4 121.5(2) . . ? C3 C4 C5 114.5(2) . . ? C3 C4 C13 104.4(2) . . ? C5 C4 C13 106.67(15) . . ? C3 C4 H4 111.7(13) . . ? C5 C4 H4 111.4(13) . . ? C13 C4 H4 107.6(12) . . ? C6 C5 C4 118.0(2) . . ? C6 C5 C7 59.46(13) . . ? C4 C5 C7 108.98(15) . . ? C6 C5 H5 117.6(12) . . ? C4 C5 H5 118.3(12) . . ? C7 C5 H5 120.9(12) . . ? C5 C6 C7 61.41(12) . . ? C5 C6 H6A 115.1(13) . . ? C7 C6 H6A 112.1(13) . . ? C5 C6 H6B 118.6(14) . . ? C7 C6 H6B 118.9(14) . . ? H6A C6 H6B 118.2(19) . . ? C8 C7 C6 119.7(2) . . ? C8 C7 C12 118.1(2) . . ? C6 C7 C12 117.8(2) . . ? C8 C7 C5 118.8(2) . . ? C6 C7 C5 59.13(13) . . ? C12 C7 C5 108.76(15) . . ? O15 C8 O9 118.4(2) . . ? O15 C8 C7 126.1(2) . . ? O9 C8 C7 115.5(2) . . ? C8 O9 C10 115.82(14) . . ? O9 C10 C11 110.0(2) . . ? O9 C10 H10A 105.8(13) . . ? C11 C10 H10A 112.4(13) . . ? O9 C10 H10B 109.5(11) . . ? C11 C10 H10B 112.4(11) . . ? H10A C10 H10B 106.5(17) . . ? C10 C11 C14 113.8(2) . . ? C10 C11 C12 109.34(15) . . ? C14 C11 C12 105.3(2) . . ? C10 C11 H11 107.4(14) . . ? C14 C11 H11 109.5(13) . . ? C12 C11 H11 111.6(14) . . ? C7 C12 C11 111.6(2) . . ? C7 C12 C13 106.42(15) . . ? C11 C12 C13 107.0(2) . . ? C7 C12 H13A 113.8(12) . . ? C11 C12 H13A 109.3(13) . . ? C13 C12 H13A 108.5(13) . . ? C1 C13 C12 106.6(2) . . ? C1 C13 C4 106.5(2) . . ? C12 C13 C4 107.48(14) . . ? C1 C13 H13B 114.0(12) . . ? C12 C13 H13B 108.6(13) . . ? C4 C13 H13B 113.3(12) . . ? C11 C14 C1 106.1(2) . . ? C11 C14 H14A 109.6(16) . . ? C1 C14 H14A 114.5(16) . . ? C11 C14 H14B 109.0(16) . . ? C1 C14 H14B 109.2(16) . . ? H14A C14 H14B 108.3(21) . . ? C3 C16 H16A 114.1(17) . . ? C3 C16 H16B 113.4(20) . . ? H16A C16 H16B 110.0(25) . . ? C3 C16 H16C 114.2(21) . . ? H16A C16 H16C 101.7(26) . . ? H16B C16 H16C 102.3(28) . . ? 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 C14 C1 C2 C3 -118.1(2) . . . . ? C13 C1 C2 C3 -2.7(2) . . . . ? C1 C2 C3 C16 178.5(2) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 C5 120.0(2) . . . . ? C16 C3 C4 C5 -59.3(2) . . . . ? C2 C3 C4 C13 3.7(2) . . . . ? C16 C3 C4 C13 -175.6(2) . . . . ? C3 C4 C5 C6 -171.6(2) . . . . ? C13 C4 C5 C6 -56.7(2) . . . . ? C3 C4 C5 C7 -106.8(2) . . . . ? C13 C4 C5 C7 8.1(2) . . . . ? C4 C5 C6 C7 96.5(2) . . . . ? C7 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 107.8(2) . . . . ? C5 C6 C7 C12 -96.2(2) . . . . ? C5 C6 C7 C5 0.0 . . . . ? C6 C5 C7 C8 -109.2(2) . . . . ? C4 C5 C7 C8 138.8(2) . . . . ? C6 C5 C7 C6 0.0 . . . . ? C4 C5 C7 C6 -112.0(2) . . . . ? C6 C5 C7 C12 111.8(2) . . . . ? C4 C5 C7 C12 -0.2(2) . . . . ? C6 C7 C8 O15 12.9(3) . . . . ? C12 C7 C8 O15 -143.0(2) . . . . ? C5 C7 C8 O15 81.7(2) . . . . ? C6 C7 C8 O9 -167.6(2) . . . . ? C12 C7 C8 O9 36.5(2) . . . . ? C5 C7 C8 O9 -98.7(2) . . . . ? O15 C8 O9 C10 -170.7(2) . . . . ? C7 C8 O9 C10 9.7(2) . . . . ? C8 O9 C10 C11 -59.3(2) . . . . ? O9 C10 C11 C14 177.8(2) . . . . ? O9 C10 C11 C12 60.4(2) . . . . ? C8 C7 C12 C11 -30.8(2) . . . . ? C6 C7 C12 C11 172.9(2) . . . . ? C5 C7 C12 C11 108.6(2) . . . . ? C8 C7 C12 C13 -147.1(2) . . . . ? C6 C7 C12 C13 56.6(2) . . . . ? C5 C7 C12 C13 -7.7(2) . . . . ? C10 C11 C12 C7 -16.4(2) . . . . ? C14 C11 C12 C7 -139.0(2) . . . . ? C10 C11 C12 C13 99.6(2) . . . . ? C14 C11 C12 C13 -23.0(2) . . . . ? C2 C1 C13 C12 -109.8(2) . . . . ? C14 C1 C13 C12 11.4(2) . . . . ? C2 C1 C13 C4 4.7(2) . . . . ? C14 C1 C13 C4 125.9(2) . . . . ? C7 C12 C13 C1 126.5(2) . . . . ? C11 C12 C13 C1 7.2(2) . . . . ? C7 C12 C13 C4 12.6(2) . . . . ? C11 C12 C13 C4 -106.7(2) . . . . ? C3 C4 C13 C1 -5.1(2) . . . . ? C5 C4 C13 C1 -126.7(2) . . . . ? C3 C4 C13 C12 108.8(2) . . . . ? C5 C4 C13 C12 -12.8(2) . . . . ? C10 C11 C14 C1 -89.5(2) . . . . ? C12 C11 C14 C1 30.2(2) . . . . ? C2 C1 C14 C11 87.9(2) . . . . ? C13 C1 C14 C11 -25.9(2) . . . . ? _refine_diff_density_max 0.166 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.040