data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_requested_journal          'Org. Biomol. Chem.'

loop_
_publ_author_name
'Steven Victor Ley'
'Darren J. Dixon'
'Richard T. Guy'
'Maria A. Palara'
'Alessandra Polara'
'Felix Rodriguez'
'Tom D. Sheppard'

_publ_contact_author_name        'Steven Victor Ley'
_publ_contact_author_address     
;
Department of Chemistry
University of Cambridge
Lensfield Road
Cambridge
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       SVL1000@CAM.AC.UK

_publ_section_title              
;
Studies on the generation of enolate anions from
butane-2,3-diacetal protected glycolic acid derivatives and subsequent
highly diastereoselective coupling reactions with aldehydes and acid
;

data_sl0323
_database_code_depnum_ccdc_archive 'CCDC 251197'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O8 S'
_chemical_formula_sum            'C14 H16 O8 S'
_chemical_formula_weight         344.33

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'
S S 0.1246 0.1234 '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)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4730(2)
_cell_length_b                   11.0206(4)
_cell_length_c                   12.9676(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.877(2)
_cell_angle_gamma                90.00
_cell_volume                     768.10(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5286
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -OH hydrogen atom was located and its position was refined
successfully.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71069
_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            6902
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3411
_reflns_number_gt                3043
_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^)+(0.0437P)^2^+0.0479P] 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   -0.14(7)
_refine_ls_number_reflns         3411
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.008
_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
S1 S 0.43645(10) 0.79864(5) 0.24697(4) 0.02235(14) Uani 1 1 d . . .
O1 O 0.6951(3) 1.10783(15) 0.33350(13) 0.0280(4) Uani 1 1 d . . .
O2 O 0.8291(3) 1.08513(13) 0.50640(11) 0.0232(3) Uani 1 1 d . . .
O3 O 1.0544(3) 0.84609(15) 0.48895(13) 0.0235(4) Uani 1 1 d D . .
H3 H 1.064(5) 0.7629(17) 0.4705(19) 0.028 Uiso 1 1 d D . .
O4 O 1.2871(3) 1.04758(17) 0.62423(13) 0.0330(4) Uani 1 1 d . . .
O5 O 1.1259(3) 0.92414(16) 0.73299(12) 0.0303(4) Uani 1 1 d . . .
O6 O 0.6731(3) 0.84586(14) 0.32878(12) 0.0224(3) Uani 1 1 d . . .
O7 O 0.2580(3) 0.75128(15) 0.30348(12) 0.0280(4) Uani 1 1 d . . .
O8 O 0.5438(3) 0.72334(16) 0.17796(13) 0.0316(4) Uani 1 1 d . . .
C1 C 0.7195(4) 1.0456(2) 0.40939(18) 0.0214(5) Uani 1 1 d . . .
C2 C 0.6402(4) 0.9143(2) 0.41962(16) 0.0198(5) Uani 1 1 d . . .
H2 H 0.4639 0.9098 0.4300 0.024 Uiso 1 1 calc R . .
C3 C 0.8199(4) 0.8690(2) 0.51725(17) 0.0197(5) Uani 1 1 d . . .
C4 C 0.8554(4) 0.9870(2) 0.58251(17) 0.0219(5) Uani 1 1 d . . .
H4 H 0.7277 0.9937 0.6281 0.026 Uiso 1 1 calc R . .
C5 C 1.1152(4) 0.9932(2) 0.64744(17) 0.0234(5) Uani 1 1 d . . .
C6 C 0.7242(4) 0.7633(2) 0.57163(18) 0.0261(5) Uani 1 1 d . . .
H6A H 0.7071 0.6922 0.5254 0.039 Uiso 1 1 calc R . .
H6B H 0.5617 0.7839 0.5882 0.039 Uiso 1 1 calc R . .
H6C H 0.8415 0.7449 0.6367 0.039 Uiso 1 1 calc R . .
C7 C 1.3710(5) 0.9080(3) 0.7974(2) 0.0376(6) Uani 1 1 d . . .
H7A H 1.3540 0.8805 0.8676 0.056 Uiso 1 1 calc R . .
H7B H 1.4609 0.9853 0.8031 0.056 Uiso 1 1 calc R . .
H7C H 1.4635 0.8473 0.7651 0.056 Uiso 1 1 calc R . .
C8 C 0.3203(4) 0.9315(2) 0.18035(17) 0.0214(5) Uani 1 1 d . . .
C9 C 0.1225(4) 0.9925(2) 0.20905(18) 0.0267(5) Uani 1 1 d . . .
H9 H 0.0452 0.9620 0.2635 0.032 Uiso 1 1 calc R . .
C10 C 0.0389(5) 1.0989(2) 0.1569(2) 0.0319(6) Uani 1 1 d . . .
H10 H -0.0957 1.1419 0.1766 0.038 Uiso 1 1 calc R . .
C11 C 0.1491(5) 1.1437(2) 0.07627(19) 0.0305(6) Uani 1 1 d . . .
C12 C 0.3480(5) 1.0809(2) 0.04940(19) 0.0318(6) Uani 1 1 d . . .
H12 H 0.4255 1.1111 -0.0050 0.038 Uiso 1 1 calc R . .
C13 C 0.4348(4) 0.9749(2) 0.10081(18) 0.0273(5) Uani 1 1 d . . .
H13 H 0.5708 0.9324 0.0819 0.033 Uiso 1 1 calc R . .
C14 C 0.0533(6) 1.2581(3) 0.0194(3) 0.0471(8) Uani 1 1 d . . .
H14A H 0.1256 1.2668 -0.0438 0.071 Uiso 1 1 calc R . .
H14B H 0.1001 1.3281 0.0655 0.071 Uiso 1 1 calc R . .
H14C H -0.1284 1.2540 -0.0006 0.071 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
S1 0.0271(3) 0.0196(3) 0.0199(3) -0.0019(2) 0.0033(2) -0.0014(2)
O1 0.0351(9) 0.0231(9) 0.0264(9) 0.0042(8) 0.0074(7) 0.0019(7)
O2 0.0304(9) 0.0152(8) 0.0234(8) -0.0002(7) 0.0033(7) -0.0010(6)
O3 0.0201(8) 0.0203(8) 0.0307(9) -0.0043(7) 0.0062(6) 0.0024(6)
O4 0.0314(9) 0.0325(10) 0.0329(9) 0.0021(9) 0.0003(7) -0.0104(8)
O5 0.0325(9) 0.0344(10) 0.0228(8) 0.0044(7) 0.0023(7) -0.0035(7)
O6 0.0241(8) 0.0240(8) 0.0196(8) -0.0044(6) 0.0049(6) 0.0016(6)
O7 0.0299(9) 0.0270(9) 0.0273(8) 0.0013(7) 0.0061(7) -0.0063(7)
O8 0.0434(10) 0.0268(9) 0.0247(9) -0.0066(7) 0.0068(8) 0.0040(8)
C1 0.0183(10) 0.0200(11) 0.0267(12) 0.0005(10) 0.0059(9) 0.0050(9)
C2 0.0220(11) 0.0199(11) 0.0188(10) -0.0038(9) 0.0073(8) 0.0008(8)
C3 0.0199(10) 0.0189(11) 0.0207(11) 0.0004(9) 0.0051(8) 0.0000(8)
C4 0.0247(11) 0.0197(11) 0.0222(11) 0.0005(10) 0.0068(9) -0.0019(9)
C5 0.0315(12) 0.0171(11) 0.0213(11) -0.0044(9) 0.0043(9) -0.0025(10)
C6 0.0308(12) 0.0203(12) 0.0270(12) 0.0037(9) 0.0049(10) -0.0043(9)
C7 0.0387(15) 0.0416(16) 0.0286(13) 0.0029(12) -0.0034(11) 0.0010(12)
C8 0.0243(11) 0.0202(12) 0.0191(11) -0.0008(9) 0.0025(9) -0.0012(9)
C9 0.0269(11) 0.0293(12) 0.0245(11) 0.0024(11) 0.0068(9) 0.0005(10)
C10 0.0266(12) 0.0340(15) 0.0353(13) 0.0062(12) 0.0062(10) 0.0048(10)
C11 0.0310(12) 0.0311(14) 0.0275(13) 0.0067(11) 0.0010(10) -0.0005(11)
C12 0.0331(14) 0.0353(15) 0.0283(12) 0.0049(12) 0.0093(11) -0.0013(11)
C13 0.0278(12) 0.0310(13) 0.0246(11) -0.0002(11) 0.0092(9) 0.0021(11)
C14 0.0469(17) 0.0432(18) 0.0508(18) 0.0201(14) 0.0084(13) 0.0122(13)

_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
S1 O8 1.4258(17) . ?
S1 O7 1.4258(17) . ?
S1 O6 1.5984(16) . ?
S1 C8 1.757(2) . ?
O1 C1 1.186(3) . ?
O2 C1 1.359(3) . ?
O2 C4 1.453(3) . ?
O3 C3 1.423(3) . ?
O3 H3 0.951(17) . ?
O4 C5 1.201(3) . ?
O5 C5 1.337(3) . ?
O5 C7 1.451(3) . ?
O6 C2 1.439(2) . ?
C1 C2 1.524(3) . ?
C2 C3 1.533(3) . ?
C2 H2 1.0000 . ?
C3 C6 1.506(3) . ?
C3 C4 1.544(3) . ?
C4 C5 1.511(3) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.384(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 C14 1.504(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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
O8 S1 O7 120.85(11) . . ?
O8 S1 O6 103.17(9) . . ?
O7 S1 O6 109.02(9) . . ?
O8 S1 C8 109.27(10) . . ?
O7 S1 C8 109.78(11) . . ?
O6 S1 C8 103.16(10) . . ?
C1 O2 C4 111.14(17) . . ?
C3 O3 H3 109.4(16) . . ?
C5 O5 C7 116.0(2) . . ?
C2 O6 S1 120.21(13) . . ?
O1 C1 O2 123.0(2) . . ?
O1 C1 C2 129.2(2) . . ?
O2 C1 C2 107.86(19) . . ?
O6 C2 C1 110.19(18) . . ?
O6 C2 C3 110.19(18) . . ?
C1 C2 C3 103.44(18) . . ?
O6 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
O3 C3 C6 113.20(18) . . ?
O3 C3 C2 108.32(18) . . ?
C6 C3 C2 114.40(18) . . ?
O3 C3 C4 105.33(17) . . ?
C6 C3 C4 114.46(18) . . ?
C2 C3 C4 99.95(17) . . ?
O2 C4 C5 107.91(17) . . ?
O2 C4 C3 105.58(16) . . ?
C5 C4 C3 110.56(18) . . ?
O2 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
O4 C5 O5 125.3(2) . . ?
O4 C5 C4 125.6(2) . . ?
O5 C5 C4 109.01(19) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.2(2) . . ?
C9 C8 S1 120.09(18) . . ?
C13 C8 S1 118.69(18) . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 C14 120.8(2) . . ?
C10 C11 C14 120.4(2) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 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
O8 S1 O6 C2 -172.73(16) . . . . ?
O7 S1 O6 C2 -43.11(18) . . . . ?
C8 S1 O6 C2 73.52(17) . . . . ?
C4 O2 C1 O1 -174.5(2) . . . . ?
C4 O2 C1 C2 5.9(2) . . . . ?
S1 O6 C2 C1 -110.67(18) . . . . ?
S1 O6 C2 C3 135.81(16) . . . . ?
O1 C1 C2 O6 36.8(3) . . . . ?
O2 C1 C2 O6 -143.54(17) . . . . ?
O1 C1 C2 C3 154.6(2) . . . . ?
O2 C1 C2 C3 -25.8(2) . . . . ?
O6 C2 C3 O3 41.1(2) . . . . ?
C1 C2 C3 O3 -76.7(2) . . . . ?
O6 C2 C3 C6 -86.2(2) . . . . ?
C1 C2 C3 C6 156.03(19) . . . . ?
O6 C2 C3 C4 151.04(17) . . . . ?
C1 C2 C3 C4 33.3(2) . . . . ?
C1 O2 C4 C5 134.66(19) . . . . ?
C1 O2 C4 C3 16.4(2) . . . . ?
O3 C3 C4 O2 81.61(19) . . . . ?
C6 C3 C4 O2 -153.39(19) . . . . ?
C2 C3 C4 O2 -30.7(2) . . . . ?
O3 C3 C4 C5 -34.8(2) . . . . ?
C6 C3 C4 C5 90.2(2) . . . . ?
C2 C3 C4 C5 -147.12(18) . . . . ?
C7 O5 C5 O4 -4.8(3) . . . . ?
C7 O5 C5 C4 172.6(2) . . . . ?
O2 C4 C5 O4 -17.3(3) . . . . ?
C3 C4 C5 O4 97.7(3) . . . . ?
O2 C4 C5 O5 165.27(17) . . . . ?
C3 C4 C5 O5 -79.7(2) . . . . ?
O8 S1 C8 C9 152.12(18) . . . . ?
O7 S1 C8 C9 17.5(2) . . . . ?
O6 S1 C8 C9 -98.63(19) . . . . ?
O8 S1 C8 C13 -29.4(2) . . . . ?
O7 S1 C8 C13 -164.10(18) . . . . ?
O6 S1 C8 C13 79.81(19) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
S1 C8 C9 C10 178.31(18) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C14 179.0(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C14 C11 C12 C13 -179.3(2) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
S1 C8 C13 C12 -178.63(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074