# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zhang, Junliang' _publ_contact_author_email jlzhang@chem.ecnu.edu.cn _publ_section_title ; Synthesis of 2-Acylfurans from 3-(1-Alkynyl)-2-alken-1-ones via the Oxidation of Gold-carbene Intermediates by H2O2 ; loop_ _publ_author_name 'Junliang Zhang' 'Tao Wang' # Attachment '- (z)-3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 755496' #TrackingRef '- (z)-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O2' _chemical_formula_weight 212.24 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 11.4578(11) _cell_length_b 10.3648(11) _cell_length_c 19.930(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.379(3) _cell_angle_gamma 90.00 _cell_volume 2341.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.552 _exptl_crystal_size_mid 0.269 _exptl_crystal_size_min 0.114 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.740457 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13121 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2073 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0927P)^2^+3.3025P] 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 SHELXL _refine_ls_extinction_coef 0.0028(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2073 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1900 _refine_ls_wR_factor_gt 0.1761 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 -0.06734(19) -0.3354(2) 0.30676(11) 0.0429(6) Uani 1 1 d . . . C2 C -0.1419(2) -0.4160(3) 0.26428(12) 0.0494(6) Uani 1 1 d . . . H2A H -0.1649 -0.3921 0.2193 0.059 Uiso 1 1 calc R . . C3 C -0.1822(2) -0.5299(3) 0.28725(14) 0.0577(7) Uani 1 1 d . . . H3A H -0.2316 -0.5826 0.2579 0.069 Uiso 1 1 calc R . . C4 C -0.1498(3) -0.5663(3) 0.35349(15) 0.0638(8) Uani 1 1 d . . . H4A H -0.1763 -0.6441 0.3690 0.077 Uiso 1 1 calc R . . C5 C -0.0784(3) -0.4876(3) 0.39657(14) 0.0633(8) Uani 1 1 d . . . H5A H -0.0573 -0.5117 0.4417 0.076 Uiso 1 1 calc R . . C6 C -0.0370(2) -0.3728(3) 0.37397(12) 0.0524(7) Uani 1 1 d . . . H6A H 0.0114 -0.3202 0.4039 0.063 Uiso 1 1 calc R . . C7 C -0.0228(2) -0.2139(2) 0.27996(11) 0.0442(6) Uani 1 1 d . . . C8 C -0.0327(2) -0.1006(2) 0.32123(12) 0.0454(6) Uani 1 1 d . . . C9 C -0.0997(2) -0.0735(3) 0.36946(12) 0.0524(7) Uani 1 1 d . . . H9A H -0.1597 -0.1240 0.3824 0.063 Uiso 1 1 calc R . . C10 C -0.0590(2) 0.0511(2) 0.39718(12) 0.0521(7) Uani 1 1 d . . . C11 C 0.0271(2) 0.0902(3) 0.36287(14) 0.0586(7) Uani 1 1 d . . . C12 C 0.1049(3) 0.2063(3) 0.3665(2) 0.0854(11) Uani 1 1 d . . . H12A H 0.1556 0.2005 0.3323 0.128 Uiso 1 1 calc R . . H12B H 0.1520 0.2107 0.4104 0.128 Uiso 1 1 calc R . . H12C H 0.0572 0.2826 0.3591 0.128 Uiso 1 1 calc R . . C13 C -0.1033(3) 0.1198(3) 0.45376(14) 0.0653(8) Uani 1 1 d . . . C14 C -0.2066(4) 0.0597(4) 0.4803(2) 0.0958(12) Uani 1 1 d . . . H14A H -0.2281 0.1117 0.5165 0.144 Uiso 1 1 calc R . . H14B H -0.1856 -0.0253 0.4970 0.144 Uiso 1 1 calc R . . H14C H -0.2721 0.0542 0.4445 0.144 Uiso 1 1 calc R . . O1 O -0.0562(2) 0.2191(2) 0.47683(11) 0.0844(8) Uani 1 1 d . . . O2 O 0.04553(16) 0.00041(18) 0.31696(10) 0.0583(6) 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 0.0416(12) 0.0491(14) 0.0396(12) -0.0008(10) 0.0112(9) 0.0032(10) C2 0.0452(13) 0.0617(16) 0.0419(12) 0.0008(11) 0.0084(10) -0.0028(11) C3 0.0501(14) 0.0601(17) 0.0633(16) -0.0033(13) 0.0096(12) -0.0099(12) C4 0.0690(18) 0.0558(17) 0.0687(18) 0.0090(14) 0.0171(14) -0.0061(14) C5 0.0770(19) 0.0641(18) 0.0484(15) 0.0128(13) 0.0086(13) 0.0044(15) C6 0.0593(15) 0.0544(15) 0.0427(13) -0.0002(11) 0.0053(11) 0.0020(12) C7 0.0436(12) 0.0485(14) 0.0406(11) 0.0004(10) 0.0070(9) 0.0009(10) C8 0.0454(13) 0.0481(14) 0.0439(12) 0.0004(10) 0.0101(10) -0.0018(10) C9 0.0578(15) 0.0571(16) 0.0451(13) 0.0057(11) 0.0170(11) 0.0099(12) C10 0.0642(16) 0.0478(15) 0.0447(13) -0.0028(11) 0.0097(11) 0.0129(12) C11 0.0581(16) 0.0554(16) 0.0631(16) -0.0074(13) 0.0115(13) 0.0018(12) C12 0.082(2) 0.066(2) 0.113(3) -0.0144(19) 0.034(2) -0.0153(17) C13 0.083(2) 0.0625(19) 0.0518(15) 0.0029(14) 0.0145(14) 0.0193(16) C14 0.096(3) 0.108(3) 0.095(3) 0.001(2) 0.054(2) 0.015(2) O1 0.133(2) 0.0601(14) 0.0623(13) -0.0172(11) 0.0215(13) 0.0026(13) O2 0.0551(11) 0.0547(11) 0.0679(12) -0.0100(9) 0.0186(9) -0.0061(8) _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 C6 1.389(3) . ? C1 C2 1.391(3) . ? C1 C7 1.487(3) . ? C2 C3 1.371(4) . ? C2 H2A 0.9300 . ? C3 C4 1.371(4) . ? C3 H3A 0.9300 . ? C4 C5 1.367(4) . ? C4 H4A 0.9300 . ? C5 C6 1.380(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C7 1.372(5) 2 ? C7 C8 1.447(3) . ? C8 C9 1.344(3) . ? C8 O2 1.389(3) . ? C9 C10 1.454(4) . ? C9 H9A 0.9300 . ? C10 C11 1.343(4) . ? C10 C13 1.484(4) . ? C11 O2 1.343(3) . ? C11 C12 1.493(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O1 1.220(4) . ? C13 C14 1.500(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C6 C1 C2 117.7(2) . . ? C6 C1 C7 122.1(2) . . ? C2 C1 C7 120.2(2) . . ? C3 C2 C1 121.4(2) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C5 C6 C1 120.4(2) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? C7 C7 C8 124.48(14) 2 . ? C7 C7 C1 120.46(13) 2 . ? C8 C7 C1 115.1(2) . . ? C9 C8 O2 109.1(2) . . ? C9 C8 C7 132.6(2) . . ? O2 C8 C7 118.2(2) . . ? C8 C9 C10 105.8(2) . . ? C8 C9 H9A 127.1 . . ? C10 C9 H9A 127.1 . . ? C11 C10 C9 107.0(2) . . ? C11 C10 C13 126.9(3) . . ? C9 C10 C13 126.1(3) . . ? C10 C11 O2 109.7(2) . . ? C10 C11 C12 134.2(3) . . ? O2 C11 C12 116.1(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 C10 120.6(3) . . ? O1 C13 C14 123.1(3) . . ? C10 C13 C14 116.3(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 O2 C8 108.3(2) . . ? 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 -1.4(4) . . . . ? C7 C1 C2 C3 178.6(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? C7 C1 C6 C5 -178.7(2) . . . . ? C6 C1 C7 C7 132.8(3) . . . 2 ? C2 C1 C7 C7 -47.2(4) . . . 2 ? C6 C1 C7 C8 -47.6(3) . . . . ? C2 C1 C7 C8 132.4(2) . . . . ? C7 C7 C8 C9 159.7(3) 2 . . . ? C1 C7 C8 C9 -19.9(4) . . . . ? C7 C7 C8 O2 -26.3(4) 2 . . . ? C1 C7 C8 O2 154.2(2) . . . . ? O2 C8 C9 C10 -0.8(3) . . . . ? C7 C8 C9 C10 173.7(2) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C8 C9 C10 C13 -177.7(2) . . . . ? C9 C10 C11 O2 -1.1(3) . . . . ? C13 C10 C11 O2 177.8(2) . . . . ? C9 C10 C11 C12 -179.3(3) . . . . ? C13 C10 C11 C12 -0.5(5) . . . . ? C11 C10 C13 O1 -4.8(5) . . . . ? C9 C10 C13 O1 173.8(3) . . . . ? C11 C10 C13 C14 175.8(3) . . . . ? C9 C10 C13 C14 -5.6(4) . . . . ? C10 C11 O2 C8 0.6(3) . . . . ? C12 C11 O2 C8 179.2(3) . . . . ? C9 C8 O2 C11 0.2(3) . . . . ? C7 C8 O2 C11 -175.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.503 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.052 # Attachment '- 2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 755497' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O3' _chemical_formula_weight 228.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6681(6) _cell_length_b 10.6721(6) _cell_length_c 11.7312(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.073(2) _cell_angle_gamma 90.00 _cell_volume 1150.69(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12533 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2020 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0710P)^2^+0.7644P] 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 2020 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.34557(19) 0.80415(13) -0.07287(14) 0.0471(4) Uani 1 1 d . . . O2 O 0.25368(15) 0.92859(12) 0.08960(11) 0.0346(4) Uani 1 1 d . . . O3 O 0.04819(19) 1.22079(15) 0.21645(14) 0.0516(5) Uani 1 1 d . . . C1 C 0.3799(2) 1.10289(19) -0.19855(18) 0.0337(5) Uani 1 1 d . . . H1A H 0.3872 1.1525 -0.1317 0.040 Uiso 1 1 calc R . . C2 C 0.4099(2) 1.1537(2) -0.29706(19) 0.0387(5) Uani 1 1 d . . . H2A H 0.4372 1.2373 -0.2963 0.046 Uiso 1 1 calc R . . C3 C 0.3992(2) 1.0803(2) -0.39642(19) 0.0419(5) Uani 1 1 d . . . H3A H 0.4189 1.1148 -0.4625 0.050 Uiso 1 1 calc R . . C4 C 0.3594(2) 0.9559(2) -0.39805(18) 0.0396(5) Uani 1 1 d . . . H4A H 0.3529 0.9066 -0.4649 0.048 Uiso 1 1 calc R . . C5 C 0.3293(2) 0.90477(19) -0.30014(17) 0.0335(5) Uani 1 1 d . . . H5A H 0.3024 0.8210 -0.3015 0.040 Uiso 1 1 calc R . . C6 C 0.3388(2) 0.97763(18) -0.19943(16) 0.0296(4) Uani 1 1 d . . . C7 C 0.3135(2) 0.91423(18) -0.09428(17) 0.0323(5) Uani 1 1 d . . . C8 C 0.2498(2) 0.98654(18) -0.01722(16) 0.0299(4) Uani 1 1 d . . . C9 C 0.1802(2) 1.09816(17) -0.02588(16) 0.0296(4) Uani 1 1 d . . . H9A H 0.1616 1.1546 -0.0893 0.035 Uiso 1 1 calc R . . C10 C 0.1409(2) 1.11220(18) 0.08179(16) 0.0300(4) Uani 1 1 d . . . C11 C 0.1894(2) 1.00655(19) 0.14839(17) 0.0325(5) Uani 1 1 d . . . C12 C 0.1849(3) 0.9633(2) 0.26702(19) 0.0459(6) Uani 1 1 d . . . H12A H 0.2306 0.8827 0.2844 0.069 Uiso 1 1 calc R . . H12B H 0.0855 0.9571 0.2662 0.069 Uiso 1 1 calc R . . H12C H 0.2356 1.0222 0.3274 0.069 Uiso 1 1 calc R . . C13 C 0.0663(2) 1.21837(19) 0.11723(18) 0.0356(5) Uani 1 1 d . . . C14 C 0.0146(3) 1.3231(2) 0.0295(2) 0.0463(6) Uani 1 1 d . . . H14A H -0.0317 1.3858 0.0638 0.069 Uiso 1 1 calc R . . H14B H -0.0538 1.2912 -0.0426 0.069 Uiso 1 1 calc R . . H14C H 0.0960 1.3594 0.0112 0.069 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 0.0753(11) 0.0288(8) 0.0429(9) 0.0035(6) 0.0268(8) 0.0127(7) O2 0.0484(8) 0.0294(7) 0.0303(7) 0.0039(5) 0.0184(6) 0.0040(6) O3 0.0749(11) 0.0481(10) 0.0439(9) -0.0039(7) 0.0362(8) 0.0098(8) C1 0.0345(10) 0.0339(11) 0.0357(10) -0.0062(8) 0.0154(8) -0.0022(8) C2 0.0357(11) 0.0359(11) 0.0494(12) -0.0001(9) 0.0204(9) -0.0062(9) C3 0.0417(12) 0.0522(14) 0.0397(11) 0.0035(10) 0.0242(9) 0.0001(10) C4 0.0438(11) 0.0466(13) 0.0322(10) -0.0049(9) 0.0174(9) 0.0036(9) C5 0.0377(10) 0.0304(10) 0.0344(10) -0.0040(8) 0.0140(8) 0.0020(8) C6 0.0298(9) 0.0299(10) 0.0311(10) -0.0015(7) 0.0122(7) 0.0034(7) C7 0.0393(10) 0.0294(10) 0.0301(10) -0.0023(8) 0.0134(8) 0.0018(8) C8 0.0382(10) 0.0288(10) 0.0256(9) 0.0018(7) 0.0140(8) -0.0007(8) C9 0.0355(10) 0.0275(10) 0.0294(9) -0.0001(7) 0.0155(8) -0.0010(8) C10 0.0347(10) 0.0286(10) 0.0299(9) -0.0017(7) 0.0148(8) -0.0032(7) C11 0.0396(10) 0.0316(10) 0.0298(10) -0.0011(8) 0.0158(8) -0.0026(8) C12 0.0624(14) 0.0464(13) 0.0357(11) 0.0084(9) 0.0251(10) 0.0047(11) C13 0.0400(11) 0.0337(11) 0.0376(11) -0.0035(8) 0.0185(9) -0.0019(8) C14 0.0538(13) 0.0378(12) 0.0531(13) 0.0050(10) 0.0251(11) 0.0132(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 O1 C7 1.221(2) . ? O2 C11 1.349(2) . ? O2 C8 1.388(2) . ? O3 C13 1.230(3) . ? C1 C2 1.386(3) . ? C1 C6 1.394(3) . ? C1 H1A 0.9300 . ? C2 C3 1.382(3) . ? C2 H2A 0.9300 . ? C3 C4 1.380(3) . ? C3 H3A 0.9300 . ? C4 C5 1.382(3) . ? C4 H4A 0.9300 . ? C5 C6 1.393(3) . ? C5 H5A 0.9300 . ? C6 C7 1.492(3) . ? C7 C8 1.462(3) . ? C8 C9 1.356(3) . ? C9 C10 1.435(3) . ? C9 H9A 0.9300 . ? C10 C11 1.369(3) . ? C10 C13 1.471(3) . ? C11 C12 1.479(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.496(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C11 O2 C8 107.42(15) . . ? C2 C1 C6 120.13(18) . . ? C2 C1 H1A 119.9 . . ? C6 C1 H1A 119.9 . . ? C3 C2 C1 120.09(19) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 120.31(19) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 119.85(19) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 120.60(19) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C1 119.02(18) . . ? C5 C6 C7 117.60(17) . . ? C1 C6 C7 123.25(17) . . ? O1 C7 C8 120.63(18) . . ? O1 C7 C6 120.67(17) . . ? C8 C7 C6 118.70(17) . . ? C9 C8 O2 109.43(16) . . ? C9 C8 C7 135.37(18) . . ? O2 C8 C7 115.14(16) . . ? C8 C9 C10 106.65(17) . . ? C8 C9 H9A 126.7 . . ? C10 C9 H9A 126.7 . . ? C11 C10 C9 106.20(17) . . ? C11 C10 C13 125.75(18) . . ? C9 C10 C13 128.04(18) . . ? O2 C11 C10 110.28(16) . . ? O2 C11 C12 116.19(17) . . ? C10 C11 C12 133.53(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C10 120.67(19) . . ? O3 C13 C14 121.31(19) . . ? C10 C13 C14 118.02(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C4 C5 C6 C7 -176.38(18) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C2 C1 C6 C7 176.21(18) . . . . ? C5 C6 C7 O1 31.1(3) . . . . ? C1 C6 C7 O1 -144.8(2) . . . . ? C5 C6 C7 C8 -149.06(19) . . . . ? C1 C6 C7 C8 35.0(3) . . . . ? C11 O2 C8 C9 -1.6(2) . . . . ? C11 O2 C8 C7 -179.17(16) . . . . ? O1 C7 C8 C9 -165.8(2) . . . . ? C6 C7 C8 C9 14.3(3) . . . . ? O1 C7 C8 O2 10.9(3) . . . . ? C6 C7 C8 O2 -168.97(16) . . . . ? O2 C8 C9 C10 1.2(2) . . . . ? C7 C8 C9 C10 178.1(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C8 C9 C10 C13 178.56(19) . . . . ? C8 O2 C11 C10 1.4(2) . . . . ? C8 O2 C11 C12 -178.68(17) . . . . ? C9 C10 C11 O2 -0.7(2) . . . . ? C13 C10 C11 O2 -179.58(18) . . . . ? C9 C10 C11 C12 179.4(2) . . . . ? C13 C10 C11 C12 0.5(4) . . . . ? C11 C10 C13 O3 3.5(3) . . . . ? C9 C10 C13 O3 -175.20(19) . . . . ? C11 C10 C13 C14 -177.0(2) . . . . ? C9 C10 C13 C14 4.3(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 0.365 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.052