# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_ap45m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Methyl 2,2-dihydroxy-2-(5-oxotetrahydrofuran-2-yl)acetate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O6'
_chemical_formula_sum            'C7 H10 O6'
_chemical_formula_weight         190.15

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 0.0000 '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 0.0000 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7699(4)
_cell_length_b                   8.2068(5)
_cell_length_c                   15.1001(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     838.95(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7449
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7978
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             877
_reflns_number_gt                871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0485P)²+0.1299P] where P=(Fo²+2Fc²)/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(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         877
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.011
_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
O3 O -0.0431(2) 0.5772(2) 0.90452(11) 0.0448(4) Uani 1 1 d . . .
O1 O 0.4687(2) 0.70912(18) 0.90271(9) 0.0391(4) Uani 1 1 d . . .
C6 C 0.2426(3) 0.4269(3) 0.92856(14) 0.0369(5) Uani 1 1 d . . .
O2 O 0.7092(2) 0.8013(2) 0.81820(11) 0.0459(4) Uani 1 1 d . . .
O6 O 0.2272(3) 0.43897(19) 1.01537(10) 0.0488(4) Uani 1 1 d . . .
O4 O 0.1886(3) 0.5679(2) 0.79182(10) 0.0471(4) Uani 1 1 d . . .
O5 O 0.3111(3) 0.3137(2) 0.89019(11) 0.0589(5) Uani 1 1 d . . .
C1 C 0.5384(3) 0.8095(2) 0.84108(13) 0.0349(4) Uani 1 1 d . . .
C5 C 0.1577(3) 0.5774(3) 0.88227(13) 0.0345(4) Uani 1 1 d . . .
C4 C 0.2584(3) 0.7318(3) 0.91542(15) 0.0378(5) Uani 1 1 d . . .
H4 H 0.2305 0.7463 0.9786 0.045 Uiso 1 1 calc R . .
C3 C 0.2056(4) 0.8873(3) 0.8655(2) 0.0530(6) Uani 1 1 d . . .
H3A H 0.0885 0.8713 0.8295 0.064 Uiso 1 1 calc R . .
H3B H 0.1818 0.9764 0.9064 0.064 Uiso 1 1 calc R . .
C2 C 0.3820(3) 0.9217(3) 0.80855(18) 0.0492(6) Uani 1 1 d . . .
H2A H 0.3525 0.9006 0.7468 0.059 Uiso 1 1 calc R . .
H2B H 0.4232 1.0344 0.8147 0.059 Uiso 1 1 calc R . .
C7 C 0.2962(4) 0.3013(3) 1.06694(18) 0.0574(6) Uani 1 1 d . . .
H7A H 0.4325 0.2806 1.0535 0.086 Uiso 1 1 calc R . .
H7B H 0.2189 0.2068 1.0526 0.086 Uiso 1 1 calc R . .
H7C H 0.2828 0.3252 1.1289 0.086 Uiso 1 1 calc R . .
H3O H -0.108(4) 0.643(3) 0.8740(18) 0.049(8) Uiso 1 1 d . . .
H4O H 0.194(5) 0.482(4) 0.7748(19) 0.054(9) Uiso 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
O3 0.0303(7) 0.0433(8) 0.0609(9) 0.0105(8) 0.0024(7) 0.0015(7)
O1 0.0314(7) 0.0403(7) 0.0456(7) 0.0103(7) 0.0001(6) -0.0013(6)
C6 0.0309(10) 0.0364(10) 0.0433(10) 0.0008(9) -0.0005(8) -0.0001(9)
O2 0.0328(8) 0.0523(9) 0.0526(8) 0.0125(8) 0.0044(6) 0.0004(8)
O6 0.0610(10) 0.0457(8) 0.0397(7) 0.0065(7) 0.0024(7) 0.0107(9)
O4 0.0617(10) 0.0439(9) 0.0358(7) -0.0029(7) -0.0007(7) 0.0086(9)
O5 0.0804(13) 0.0426(9) 0.0538(9) -0.0016(8) 0.0014(10) 0.0234(10)
C1 0.0353(10) 0.0343(10) 0.0351(9) -0.0004(8) -0.0029(8) -0.0027(9)
C5 0.0315(10) 0.0352(10) 0.0367(9) -0.0004(9) 0.0023(8) 0.0027(9)
C4 0.0345(11) 0.0362(10) 0.0427(11) -0.0040(9) 0.0080(9) 0.0009(9)
C3 0.0389(11) 0.0343(11) 0.0860(17) 0.0060(12) 0.0056(13) 0.0061(10)
C2 0.0417(12) 0.0414(12) 0.0645(13) 0.0137(12) -0.0014(11) 0.0041(10)
C7 0.0580(14) 0.0580(15) 0.0562(13) 0.0185(12) -0.0063(12) 0.0074(14)

_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
O3 C5 1.400(3) . ?
O3 H3O 0.84(3) . ?
O1 C1 1.330(2) . ?
O1 C4 1.448(3) . ?
C6 O5 1.189(3) . ?
C6 O6 1.319(3) . ?
C6 C5 1.532(3) . ?
O2 C1 1.209(3) . ?
O6 C7 1.450(3) . ?
O4 C5 1.384(3) . ?
O4 H4O 0.75(3) . ?
C1 C2 1.487(3) . ?
C5 C4 1.523(3) . ?
C4 C3 1.525(3) . ?
C4 H4 0.9800 . ?
C3 C2 1.499(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C5 O3 H3O 112(2) . . ?
C1 O1 C4 111.24(17) . . ?
O5 C6 O6 125.0(2) . . ?
O5 C6 C5 123.7(2) . . ?
O6 C6 C5 111.31(17) . . ?
C6 O6 C7 116.74(18) . . ?
C5 O4 H4O 113(2) . . ?
O2 C1 O1 120.37(19) . . ?
O2 C1 C2 128.4(2) . . ?
O1 C1 C2 111.23(19) . . ?
O4 C5 O3 112.57(18) . . ?
O4 C5 C4 107.67(19) . . ?
O3 C5 C4 110.91(17) . . ?
O4 C5 C6 110.35(18) . . ?
O3 C5 C6 104.69(18) . . ?
C4 C5 C6 110.67(16) . . ?
O1 C4 C5 106.83(16) . . ?
O1 C4 C3 105.83(18) . . ?
C5 C4 C3 115.38(19) . . ?
O1 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C2 C3 C4 104.73(19) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C1 C2 C3 105.15(18) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 974676'
