data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Steven V. Ley' 'Marianne F. Buffet' 'Dominic J. Reynolds' 'R. Ian Storer' 'Darren J. Dixon' _publ_contact_author_name 'Prof Steven V Ley' _publ_contact_author_address ; Cambridge UNITED KINGDOM ; _publ_contact_author_email SVL1000@CAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (g)- and pyranyl (d)-lactols. ; data_dd0401 _database_code_depnum_ccdc_archive 'CCDC 229787' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 F O3' _chemical_formula_sum 'C15 H17 F O3' _chemical_formula_weight 264.29 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' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.8956(2) _cell_length_b 8.0263(2) _cell_length_c 25.0635(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1387.17(7) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 7782 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; High temperature form. For low temperature (monoclinic) form, see SL9904 (=DD0402). ; _diffrn_ambient_temperature 250(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 8408 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3124 _reflns_number_gt 2234 _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^)+(0.0878P)^2^+0.3660P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(17) _refine_ls_number_reflns 3124 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1868 _refine_ls_wR_factor_gt 0.1631 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 F1 F 1.4682(5) 0.7634(3) 0.84564(8) 0.1226(9) Uani 1 1 d . . . O1 O 0.6449(4) 0.0344(4) 0.40120(14) 0.1180(10) Uani 1 1 d D . . H1 H 0.520(4) -0.030(5) 0.4042(19) 0.142 Uiso 1 1 d D . . O2 O 0.7796(3) 0.6482(2) 0.59100(9) 0.0790(6) Uani 1 1 d . . . O3 O 1.0586(3) 0.7768(3) 0.65880(8) 0.0804(6) Uani 1 1 d . . . C1 C 0.6096(9) 0.1433(6) 0.4453(2) 0.145(2) Uani 1 1 d . . . H1A H 0.4701 0.1457 0.4526 0.173 Uiso 1 1 calc R . . H1B H 0.6745 0.0984 0.4770 0.173 Uiso 1 1 calc R . . C2 C 0.6716(11) 0.2998(5) 0.43707(16) 0.139(2) Uani 1 1 d . . . H2A H 0.6021 0.3461 0.4064 0.166 Uiso 1 1 calc R . . H2B H 0.8097 0.2965 0.4279 0.166 Uiso 1 1 calc R . . C3 C 0.6447(6) 0.4129(4) 0.48339(13) 0.0909(10) Uani 1 1 d . . . C4 C 0.6246(5) 0.4988(4) 0.52111(11) 0.0704(7) Uani 1 1 d . . . C5 C 0.5960(5) 0.6111(4) 0.56612(11) 0.0683(7) Uani 1 1 d . . . H5 H 0.5108 0.5561 0.5926 0.082 Uiso 1 1 calc R . . C6 C 0.5082(6) 0.7773(4) 0.55109(13) 0.0825(9) Uani 1 1 d . . . H6A H 0.3665 0.7744 0.5538 0.099 Uiso 1 1 calc R . . H6B H 0.5449 0.8095 0.5148 0.099 Uiso 1 1 calc R . . C7 C 0.5947(5) 0.8949(4) 0.59186(13) 0.0796(8) Uani 1 1 d . . . H7A H 0.5199 0.8938 0.6251 0.095 Uiso 1 1 calc R . . H7B H 0.6001 1.0091 0.5781 0.095 Uiso 1 1 calc R . . C8 C 0.7965(5) 0.8247(3) 0.60026(12) 0.0703(7) Uani 1 1 d . . . H8 H 0.8871 0.8742 0.5740 0.084 Uiso 1 1 calc R . . C9 C 0.8727(5) 0.8509(4) 0.65573(11) 0.0709(7) Uani 1 1 d . . . H9A H 0.8815 0.9703 0.6636 0.085 Uiso 1 1 calc R . . H9B H 0.7853 0.7995 0.6818 0.085 Uiso 1 1 calc R . . C10 C 1.1521(4) 0.7759(4) 0.70739(10) 0.0663(7) Uani 1 1 d . . . C11 C 1.0938(5) 0.8708(4) 0.75073(11) 0.0769(9) Uani 1 1 d . . . H11 H 0.9830 0.9386 0.7485 0.092 Uiso 1 1 calc R . . C12 C 1.2017(6) 0.8641(4) 0.79753(12) 0.0872(10) Uani 1 1 d . . . H12 H 1.1638 0.9261 0.8276 0.105 Uiso 1 1 calc R . . C13 C 1.3618(6) 0.7672(4) 0.79921(12) 0.0813(9) Uani 1 1 d . . . C14 C 1.4209(5) 0.6722(4) 0.75728(13) 0.0799(9) Uani 1 1 d . . . H14 H 1.5320 0.6048 0.7600 0.096 Uiso 1 1 calc R . . C15 C 1.3148(5) 0.6768(4) 0.71099(12) 0.0753(8) Uani 1 1 d . . . H15 H 1.3533 0.6120 0.6816 0.090 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 F1 0.184(2) 0.1037(16) 0.0801(13) 0.0039(12) -0.0422(14) -0.0035(16) O1 0.0965(18) 0.1038(19) 0.154(2) -0.0667(18) 0.0015(18) -0.0138(15) O2 0.0912(15) 0.0639(11) 0.0820(13) -0.0203(10) -0.0210(11) 0.0136(10) O3 0.0802(13) 0.0998(16) 0.0613(11) -0.0308(11) 0.0026(9) 0.0112(12) C1 0.168(5) 0.106(3) 0.159(4) -0.059(3) 0.050(4) -0.035(3) C2 0.264(7) 0.075(2) 0.077(2) -0.0142(19) 0.018(3) -0.014(4) C3 0.132(3) 0.0694(18) 0.0709(19) -0.0088(16) 0.002(2) -0.005(2) C4 0.088(2) 0.0620(15) 0.0612(15) -0.0035(13) 0.0003(14) -0.0064(15) C5 0.0843(19) 0.0643(16) 0.0565(14) -0.0044(12) 0.0002(13) -0.0037(14) C6 0.100(2) 0.075(2) 0.0728(18) -0.0042(15) -0.0127(16) 0.0119(17) C7 0.109(2) 0.0609(15) 0.0687(16) -0.0043(13) -0.0018(17) 0.0149(16) C8 0.089(2) 0.0613(15) 0.0606(15) -0.0098(13) 0.0050(14) -0.0010(14) C9 0.0851(19) 0.0629(16) 0.0646(15) -0.0169(13) 0.0040(14) 0.0035(15) C10 0.0771(18) 0.0653(15) 0.0564(14) -0.0131(12) 0.0064(12) -0.0059(14) C11 0.096(2) 0.0713(17) 0.0629(16) -0.0199(14) 0.0045(15) 0.0043(16) C12 0.128(3) 0.0743(19) 0.0599(16) -0.0168(15) 0.0040(17) -0.008(2) C13 0.116(3) 0.0642(17) 0.0639(17) 0.0034(14) -0.0117(17) -0.0153(19) C14 0.090(2) 0.0729(19) 0.0767(19) 0.0050(16) -0.0042(16) -0.0057(17) C15 0.083(2) 0.0740(18) 0.0690(17) -0.0127(15) 0.0107(14) 0.0001(16) _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 F1 C13 1.376(4) . ? O1 C1 1.430(5) . ? O1 H1 1.008(19) . ? O2 C8 1.441(3) . ? O2 C5 1.443(4) . ? O3 C10 1.378(3) . ? O3 C9 1.415(4) . ? C1 C2 1.342(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.486(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.178(4) . ? C4 C5 1.457(4) . ? C5 C6 1.512(4) . ? C5 H5 0.9900 . ? C6 C7 1.514(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.516(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.501(4) . ? C8 H8 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C15 1.378(4) . ? C10 C11 1.386(4) . ? C11 C12 1.390(5) . ? C11 H11 0.9400 . ? C12 C13 1.351(5) . ? C12 H12 0.9400 . ? C13 C14 1.361(5) . ? C14 C15 1.372(4) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? 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 C1 O1 H1 96(3) . . ? C8 O2 C5 110.1(2) . . ? C10 O3 C9 118.3(2) . . ? C2 C1 O1 113.5(4) . . ? C2 C1 H1A 108.9 . . ? O1 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? O1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C1 C2 C3 114.3(4) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 178.0(4) . . ? C3 C4 C5 177.3(3) . . ? O2 C5 C4 110.1(2) . . ? O2 C5 C6 106.1(2) . . ? C4 C5 C6 114.0(2) . . ? O2 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C6 C5 H5 108.8 . . ? C5 C6 C7 103.0(2) . . ? C5 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? C5 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? C6 C7 C8 102.9(2) . . ? C6 C7 H7A 111.2 . . ? C8 C7 H7A 111.2 . . ? C6 C7 H7B 111.2 . . ? C8 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? O2 C8 C9 108.4(2) . . ? O2 C8 C7 105.6(3) . . ? C9 C8 C7 113.4(3) . . ? O2 C8 H8 109.8 . . ? C9 C8 H8 109.8 . . ? C7 C8 H8 109.8 . . ? O3 C9 C8 108.0(2) . . ? O3 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O3 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O3 C10 C15 116.2(2) . . ? O3 C10 C11 123.6(3) . . ? C15 C10 C11 120.1(3) . . ? C10 C11 C12 119.0(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 122.9(3) . . ? C12 C13 F1 118.3(3) . . ? C14 C13 F1 118.7(4) . . ? C13 C14 C15 118.6(3) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C14 C15 C10 120.3(3) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? 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 O1 C1 C2 C3 -177.3(5) . . . . ? C1 C2 C3 C4 36(15) . . . . ? C2 C3 C4 C5 -170(12) . . . . ? C8 O2 C5 C4 133.2(3) . . . . ? C8 O2 C5 C6 9.4(3) . . . . ? C3 C4 C5 O2 -119(7) . . . . ? C3 C4 C5 C6 0(8) . . . . ? O2 C5 C6 C7 -27.8(3) . . . . ? C4 C5 C6 C7 -149.1(3) . . . . ? C5 C6 C7 C8 34.8(3) . . . . ? C5 O2 C8 C9 134.8(3) . . . . ? C5 O2 C8 C7 12.9(3) . . . . ? C6 C7 C8 O2 -29.9(3) . . . . ? C6 C7 C8 C9 -148.4(3) . . . . ? C10 O3 C9 C8 -175.9(3) . . . . ? O2 C8 C9 O3 61.7(3) . . . . ? C7 C8 C9 O3 178.6(2) . . . . ? C9 O3 C10 C15 168.5(3) . . . . ? C9 O3 C10 C11 -13.3(4) . . . . ? O3 C10 C11 C12 -178.2(3) . . . . ? C15 C10 C11 C12 0.0(5) . . . . ? C10 C11 C12 C13 0.9(5) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C11 C12 C13 F1 179.3(3) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? F1 C13 C14 C15 -179.8(3) . . . . ? C13 C14 C15 C10 0.0(5) . . . . ? O3 C10 C15 C14 177.9(3) . . . . ? C11 C10 C15 C14 -0.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.309 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.036