data_7150362
_journal_name_full  'Organic and Biomolecular Chemistry'
_journal_year      2004
loop_
_publ_author_name
'Steven V. Ley'
'Marianne F. Buffet'
'Dominic J. Reynolds'
'R. Ian Storer'
'Darren J. Dixon'
_publ_section_title
;
Anomeric oxygen to carbon rearrangements of alkynyl
tributylstannane derivatives of furanyl (g)- and pyranyl (d)-lactols.
;
_chemical_formula_moiety  'C15 H17 F O3'
_chemical_formula_sum  'C15 H17 F O3'
_chemical_formula_weight  264.29
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
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)
_exptl_crystal_density_diffrn  1.265
_diffrn_ambient_temperature  250(2)
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)
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 . ?