data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jonathan Burton' 'David G. Hulcoop' _publ_contact_author_name 'Jonathan Burton' _publ_contact_author_address ; Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email JWB1004@HERMES.CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis of fused tricyclic g-lactones mediated by manganese(III) acetate. ; data_jb0402 _database_code_depnum_ccdc_archive 'CCDC 277611' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 O6' _chemical_formula_sum 'C14 H18 O6' _chemical_formula_weight 282.28 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6093(2) _cell_length_b 12.2244(3) _cell_length_c 14.2977(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.2810(10) _cell_angle_gamma 90.00 _cell_volume 1327.78(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7953 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11938 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3033 _reflns_number_gt 2422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0557P)^2^+0.5948P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.040(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3033 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.2492(2) 0.01408(15) 0.50521(11) 0.0319(4) Uani 1 1 d . . . C2 C 0.2221(2) 0.12894(15) 0.53658(12) 0.0366(4) Uani 1 1 d . . . H2A H 0.2541 0.1365 0.6044 0.044 Uiso 1 1 calc R . . H2B H 0.0976 0.1509 0.5247 0.044 Uiso 1 1 calc R . . C3 C 0.3422(2) 0.19911(14) 0.47921(11) 0.0315(4) Uani 1 1 d . . . H3 H 0.4503 0.2218 0.5174 0.038 Uiso 1 1 calc R . . C4 C 0.2532(2) 0.29720(14) 0.42991(12) 0.0353(4) Uani 1 1 d . . . H4A H 0.3419 0.3507 0.4106 0.042 Uiso 1 1 calc R . . H4B H 0.1723 0.3342 0.4716 0.042 Uiso 1 1 calc R . . C5 C 0.1508(2) 0.24844(14) 0.34373(12) 0.0300(4) Uani 1 1 d . . . H5 H 0.0333 0.2207 0.3609 0.036 Uiso 1 1 calc R . . C6 C 0.1310(2) 0.32536(15) 0.25954(13) 0.0375(4) Uani 1 1 d . . . H6A H 0.0351 0.3008 0.2147 0.045 Uiso 1 1 calc R . . H6B H 0.1062 0.4011 0.2796 0.045 Uiso 1 1 calc R . . C7 C 0.3091(2) 0.31828(14) 0.21623(13) 0.0353(4) Uani 1 1 d . . . H7A H 0.3977 0.3639 0.2514 0.042 Uiso 1 1 calc R . . H7B H 0.3001 0.3426 0.1501 0.042 Uiso 1 1 calc R . . C8 C 0.3584(2) 0.19562(13) 0.22335(11) 0.0260(3) Uani 1 1 d . . . C9 C 0.2683(2) 0.15307(13) 0.31268(11) 0.0252(3) Uani 1 1 d . . . H9 H 0.1917 0.0891 0.2947 0.030 Uiso 1 1 calc R . . C10 C 0.3879(2) 0.12214(14) 0.39917(11) 0.0294(4) Uani 1 1 d . . . H10 H 0.5149 0.1288 0.3856 0.035 Uiso 1 1 calc R . . C11 C 0.5565(2) 0.17831(13) 0.23012(10) 0.0266(3) Uani 1 1 d . . . C12 C 0.2786(2) 0.13705(13) 0.13637(11) 0.0275(4) Uani 1 1 d . . . C13 C 0.7812(2) 0.04582(17) 0.22291(13) 0.0390(4) Uani 1 1 d . . . H13A H 0.7948 -0.0334 0.2154 0.059 Uiso 1 1 calc R . . H13B H 0.8297 0.0678 0.2851 0.059 Uiso 1 1 calc R . . H13C H 0.8442 0.0840 0.1747 0.059 Uiso 1 1 calc R . . C14 C 0.2888(3) 0.12300(19) -0.02800(12) 0.0448(5) Uani 1 1 d . . . H14A H 0.2921 0.1792 -0.0768 0.067 Uiso 1 1 calc R . . H14B H 0.1669 0.0996 -0.0216 0.067 Uiso 1 1 calc R . . H14C H 0.3598 0.0601 -0.0453 0.067 Uiso 1 1 calc R . . O15 O 0.34752(16) 0.01209(10) 0.42920(8) 0.0348(3) Uani 1 1 d . . . O16 O 0.19677(17) -0.06991(11) 0.53792(9) 0.0432(3) Uani 1 1 d . . . O17 O 0.15787(16) 0.07415(12) 0.13487(9) 0.0444(4) Uani 1 1 d . . . O18 O 0.66409(16) 0.24722(10) 0.25130(9) 0.0386(3) Uani 1 1 d . . . O19 O 0.59598(14) 0.07405(9) 0.21345(8) 0.0308(3) Uani 1 1 d . . . O20 O 0.35911(17) 0.16748(11) 0.06008(8) 0.0410(3) 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 0.0307(8) 0.0368(10) 0.0273(8) 0.0026(7) -0.0063(6) -0.0037(7) C2 0.0398(9) 0.0400(10) 0.0306(9) -0.0028(7) 0.0068(7) -0.0032(8) C3 0.0325(8) 0.0320(9) 0.0298(8) -0.0039(7) -0.0011(6) -0.0055(7) C4 0.0400(9) 0.0292(9) 0.0369(9) -0.0071(7) 0.0032(7) -0.0018(7) C5 0.0267(8) 0.0279(9) 0.0354(9) -0.0035(7) 0.0031(6) 0.0033(6) C6 0.0381(9) 0.0305(9) 0.0435(10) -0.0012(8) -0.0020(8) 0.0103(7) C7 0.0421(10) 0.0237(9) 0.0403(9) 0.0063(7) 0.0039(7) 0.0051(7) C8 0.0269(8) 0.0239(8) 0.0273(8) 0.0022(6) 0.0028(6) 0.0003(6) C9 0.0243(7) 0.0254(8) 0.0258(7) 0.0006(6) 0.0017(6) 0.0019(6) C10 0.0270(8) 0.0328(9) 0.0284(8) 0.0019(7) 0.0016(6) 0.0005(6) C11 0.0289(8) 0.0272(8) 0.0237(7) 0.0032(6) 0.0025(6) -0.0043(6) C12 0.0246(8) 0.0303(9) 0.0278(8) 0.0032(6) 0.0025(6) 0.0031(6) C13 0.0240(8) 0.0516(12) 0.0414(10) -0.0066(8) 0.0011(7) 0.0076(7) C14 0.0459(11) 0.0640(14) 0.0243(8) 0.0007(8) -0.0001(7) -0.0088(9) O15 0.0475(7) 0.0298(7) 0.0271(6) 0.0025(5) 0.0020(5) 0.0060(5) O16 0.0463(7) 0.0409(8) 0.0413(7) 0.0123(6) -0.0063(6) -0.0089(6) O17 0.0367(7) 0.0626(9) 0.0343(7) -0.0083(6) 0.0067(5) -0.0184(6) O18 0.0345(6) 0.0328(7) 0.0477(7) 0.0011(6) -0.0025(5) -0.0100(5) O19 0.0230(5) 0.0303(6) 0.0393(6) -0.0042(5) 0.0031(4) 0.0007(4) O20 0.0458(7) 0.0522(8) 0.0253(6) 0.0033(5) 0.0030(5) -0.0165(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 C1 O16 1.206(2) . ? C1 O15 1.354(2) . ? C1 C2 1.492(3) . ? C2 C3 1.526(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(3) . ? C3 C10 1.537(2) . ? C3 H3 1.0000 . ? C4 C5 1.540(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.528(2) . ? C5 C9 1.550(2) . ? C5 H5 1.0000 . ? C6 C7 1.524(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.548(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C11 1.520(2) . ? C8 C12 1.530(2) . ? C8 C9 1.572(2) . ? C9 C10 1.540(2) . ? C9 H9 1.0000 . ? C10 O15 1.450(2) . ? C10 H10 1.0000 . ? C11 O18 1.2015(19) . ? C11 O19 1.334(2) . ? C12 O17 1.197(2) . ? C12 O20 1.3341(19) . ? C13 O19 1.4498(19) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O20 1.446(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 O16 C1 O15 120.42(16) . . ? O16 C1 C2 129.07(17) . . ? O15 C1 C2 110.51(14) . . ? C1 C2 C3 105.66(14) . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C2 C3 C4 115.18(15) . . ? C2 C3 C10 102.95(13) . . ? C4 C3 C10 104.48(13) . . ? C2 C3 H3 111.2 . . ? C4 C3 H3 111.2 . . ? C10 C3 H3 111.2 . . ? C3 C4 C5 104.82(14) . . ? C3 C4 H4A 110.8 . . ? C5 C4 H4A 110.8 . . ? C3 C4 H4B 110.8 . . ? C5 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? C6 C5 C4 114.50(15) . . ? C6 C5 C9 105.65(13) . . ? C4 C5 C9 104.28(13) . . ? C6 C5 H5 110.7 . . ? C4 C5 H5 110.7 . . ? C9 C5 H5 110.7 . . ? C7 C6 C5 103.61(13) . . ? C7 C6 H6A 111.0 . . ? C5 C6 H6A 111.0 . . ? C7 C6 H6B 111.0 . . ? C5 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C6 C7 C8 104.25(14) . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C11 C8 C12 109.43(13) . . ? C11 C8 C7 112.03(13) . . ? C12 C8 C7 108.44(13) . . ? C11 C8 C9 112.28(12) . . ? C12 C8 C9 109.53(12) . . ? C7 C8 C9 104.98(13) . . ? C10 C9 C5 106.20(13) . . ? C10 C9 C8 117.93(12) . . ? C5 C9 C8 105.63(13) . . ? C10 C9 H9 108.9 . . ? C5 C9 H9 108.9 . . ? C8 C9 H9 108.9 . . ? O15 C10 C3 106.66(13) . . ? O15 C10 C9 109.87(13) . . ? C3 C10 C9 107.40(13) . . ? O15 C10 H10 110.9 . . ? C3 C10 H10 110.9 . . ? C9 C10 H10 110.9 . . ? O18 C11 O19 123.88(15) . . ? O18 C11 C8 125.29(15) . . ? O19 C11 C8 110.76(13) . . ? O17 C12 O20 123.52(15) . . ? O17 C12 C8 125.69(14) . . ? O20 C12 C8 110.78(13) . . ? O19 C13 H13A 109.5 . . ? O19 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O19 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O20 C14 H14A 109.5 . . ? O20 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O20 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 O15 C10 110.92(13) . . ? C11 O19 C13 116.01(13) . . ? C12 O20 C14 116.29(13) . . ? 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 O16 C1 C2 C3 171.15(16) . . . . ? O15 C1 C2 C3 -8.93(18) . . . . ? C1 C2 C3 C4 129.12(15) . . . . ? C1 C2 C3 C10 16.07(17) . . . . ? C2 C3 C4 C5 -77.62(17) . . . . ? C10 C3 C4 C5 34.53(17) . . . . ? C3 C4 C5 C6 -149.85(14) . . . . ? C3 C4 C5 C9 -34.89(17) . . . . ? C4 C5 C6 C7 78.83(17) . . . . ? C9 C5 C6 C7 -35.32(17) . . . . ? C5 C6 C7 C8 40.29(17) . . . . ? C6 C7 C8 C11 -151.72(14) . . . . ? C6 C7 C8 C12 87.40(16) . . . . ? C6 C7 C8 C9 -29.60(17) . . . . ? C6 C5 C9 C10 142.69(14) . . . . ? C4 C5 C9 C10 21.64(17) . . . . ? C6 C5 C9 C8 16.69(16) . . . . ? C4 C5 C9 C8 -104.36(14) . . . . ? C11 C8 C9 C10 11.40(19) . . . . ? C12 C8 C9 C10 133.19(14) . . . . ? C7 C8 C9 C10 -110.55(15) . . . . ? C11 C8 C9 C5 129.84(13) . . . . ? C12 C8 C9 C5 -108.38(14) . . . . ? C7 C8 C9 C5 7.88(16) . . . . ? C2 C3 C10 O15 -17.96(16) . . . . ? C4 C3 C10 O15 -138.65(13) . . . . ? C2 C3 C10 C9 99.78(15) . . . . ? C4 C3 C10 C9 -20.90(17) . . . . ? C5 C9 C10 O15 115.07(14) . . . . ? C8 C9 C10 O15 -126.80(14) . . . . ? C5 C9 C10 C3 -0.56(17) . . . . ? C8 C9 C10 C3 117.57(15) . . . . ? C12 C8 C11 O18 138.19(16) . . . . ? C7 C8 C11 O18 17.9(2) . . . . ? C9 C8 C11 O18 -99.97(18) . . . . ? C12 C8 C11 O19 -44.67(17) . . . . ? C7 C8 C11 O19 -164.98(13) . . . . ? C9 C8 C11 O19 77.17(16) . . . . ? C11 C8 C12 O17 128.32(18) . . . . ? C7 C8 C12 O17 -109.21(19) . . . . ? C9 C8 C12 O17 4.8(2) . . . . ? C11 C8 C12 O20 -53.28(17) . . . . ? C7 C8 C12 O20 69.19(17) . . . . ? C9 C8 C12 O20 -176.77(13) . . . . ? O16 C1 O15 C10 176.98(14) . . . . ? C2 C1 O15 C10 -2.95(18) . . . . ? C3 C10 O15 C1 13.58(17) . . . . ? C9 C10 O15 C1 -102.52(14) . . . . ? O18 C11 O19 C13 0.4(2) . . . . ? C8 C11 O19 C13 -176.75(13) . . . . ? O17 C12 O20 C14 2.1(3) . . . . ? C8 C12 O20 C14 -176.33(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.344 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.084