# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1419551'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Butyl 2-deoxy-3,6-anhydro-beta-D-arabinohexofuranoside'
_chemical_name_common            ?
_chemical_melting_point          350.15-351.15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 O5'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   5.3124(4)
_cell_length_b                   7.0459(8)
_cell_length_c                   29.215(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1093.53(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3701
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      67.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7889
_exptl_absorpt_correction_T_max  0.8284
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3856
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         64.99
_reflns_number_total             1716
_reflns_number_gt                1712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0894P)²+1.1362P] 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     SHELXL
_refine_ls_extinction_coef       0.118(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_number_reflns         1716
_refine_ls_number_parameters     140
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_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 0.2257(7) -0.3050(4) 0.06859(11) 0.0231(8) Uani 1 1 d . . .
H1 H 0.3157 -0.3976 0.0497 0.028 Uiso 1 1 calc R . .
C2 C 0.3807(7) -0.2697(5) 0.11160(12) 0.0256(8) Uani 1 1 d . . .
H2A H 0.2782 -0.2111 0.1352 0.031 Uiso 1 1 calc R . .
H2B H 0.4480 -0.3880 0.1234 0.031 Uiso 1 1 calc R . .
C3 C 0.5089(6) -0.0453(4) 0.05651(10) 0.0182(7) Uani 1 1 d . . .
H3 H 0.6268 -0.0702 0.0314 0.022 Uiso 1 1 calc R . .
C4 C 0.2428(6) -0.1121(4) 0.04509(10) 0.0186(8) Uani 1 1 d . . .
H4 H 0.2156 -0.1218 0.0120 0.022 Uiso 1 1 calc R . .
C5 C 0.2138(6) 0.1758(4) 0.08601(10) 0.0188(7) Uani 1 1 d . . .
H5 H 0.1340 0.2973 0.0785 0.023 Uiso 1 1 calc R . .
C6 C 0.4735(6) 0.1660(4) 0.06479(10) 0.0188(7) Uani 1 1 d . . .
H6 H 0.6039 0.2195 0.0847 0.023 Uiso 1 1 calc R . .
C7 C 0.0103(7) 0.1899(5) 0.15819(12) 0.0281(8) Uani 1 1 d . . .
H7A H -0.1170 0.0986 0.1491 0.034 Uiso 1 1 calc R . .
H7B H -0.0531 0.3164 0.1520 0.034 Uiso 1 1 calc R . .
C8 C 0.0696(9) 0.1684(10) 0.20842(14) 0.0580(15) Uani 1 1 d U . .
H8A H -0.0831 0.1941 0.2255 0.070 Uiso 1 1 calc R . .
H8B H 0.1138 0.0368 0.2139 0.070 Uiso 1 1 calc R . .
C9 C 0.2662(12) 0.2848(10) 0.22691(18) 0.0651(15) Uani 1 1 d U . .
H9A H 0.2186 0.4173 0.2243 0.078 Uiso 1 1 calc R . .
H9B H 0.4189 0.2659 0.2093 0.078 Uiso 1 1 calc R . .
C10 C 0.3177(14) 0.2369(14) 0.27766(18) 0.086(2) Uani 1 1 d U . .
H10A H 0.1628 0.2421 0.2946 0.129 Uiso 1 1 calc R . .
H10B H 0.4344 0.3272 0.2901 0.129 Uiso 1 1 calc R . .
H10C H 0.3877 0.1117 0.2799 0.129 Uiso 1 1 calc R . .
O1 O -0.0190(5) -0.3732(3) 0.07592(9) 0.0284(7) Uani 1 1 d . . .
H1A H -0.1082 -0.2869 0.0855 0.043 Uiso 1 1 calc R . .
O2 O 0.5796(4) -0.1457(3) 0.09813(8) 0.0221(6) Uani 1 1 d . . .
O3 O 0.4578(4) 0.2607(3) 0.02189(7) 0.0231(6) Uani 1 1 d . . .
H3A H 0.5925 0.2508 0.0084 0.035 Uiso 1 1 calc R . .
O4 O 0.0756(4) 0.0234(3) 0.06595(7) 0.0193(6) Uani 1 1 d . . .
O5 O 0.2381(4) 0.1577(4) 0.13325(7) 0.0251(6) 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 0.0211(17) 0.0164(16) 0.0317(17) -0.0014(13) 0.0039(15) 0.0040(13)
C2 0.0238(17) 0.0234(16) 0.0295(17) 0.0066(15) 0.0019(14) 0.0044(14)
C3 0.0160(17) 0.0202(15) 0.0185(14) 0.0005(12) 0.0000(11) -0.0004(13)
C4 0.0186(17) 0.0176(16) 0.0195(14) -0.0029(12) -0.0012(12) 0.0009(13)
C5 0.0193(16) 0.0156(15) 0.0215(15) -0.0014(12) -0.0008(13) -0.0011(13)
C6 0.0208(16) 0.0182(15) 0.0175(14) 0.0002(12) 0.0015(13) -0.0020(13)
C7 0.0230(18) 0.0379(19) 0.0235(16) -0.0033(14) 0.0061(14) 0.0003(16)
C8 0.038(2) 0.106(4) 0.030(2) -0.010(2) 0.0038(18) 0.008(3)
C9 0.057(3) 0.081(4) 0.057(3) -0.015(3) 0.004(3) 0.002(3)
C10 0.072(4) 0.143(6) 0.042(3) -0.019(3) -0.009(3) 0.015(4)
O1 0.0195(12) 0.0162(11) 0.0496(16) -0.0003(10) 0.0051(11) -0.0004(10)
O2 0.0197(12) 0.0224(11) 0.0241(11) 0.0066(9) -0.0025(9) 0.0014(10)
O3 0.0234(12) 0.0248(12) 0.0212(11) 0.0059(9) 0.0011(10) -0.0018(10)
O4 0.0158(11) 0.0174(11) 0.0248(11) -0.0002(9) 0.0001(9) 0.0006(9)
O5 0.0204(12) 0.0375(14) 0.0175(11) -0.0031(10) 0.0012(9) 0.0022(11)

_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 O1 1.403(4) . ?
C1 C2 1.523(5) . ?
C1 C4 1.525(4) . ?
C1 H1 0.9800 . ?
C2 O2 1.426(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.456(4) . ?
C3 C6 1.520(4) . ?
C3 C4 1.527(5) . ?
C3 H3 0.9800 . ?
C4 O4 1.440(4) . ?
C4 H4 0.9800 . ?
C5 O5 1.392(4) . ?
C5 O4 1.426(4) . ?
C5 C6 1.514(4) . ?
C5 H5 0.9800 . ?
C6 O3 1.422(4) . ?
C6 H6 0.9800 . ?
C7 O5 1.431(4) . ?
C7 C8 1.508(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.434(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.545(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 H1A 0.8200 . ?
O3 H3A 0.8200 . ?

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
O1 C1 C2 115.5(3) . . ?
O1 C1 C4 115.4(3) . . ?
C2 C1 C4 101.2(3) . . ?
O1 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C4 C1 H1 108.1 . . ?
O2 C2 C1 105.8(3) . . ?
O2 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
O2 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
O2 C3 C6 112.0(3) . . ?
O2 C3 C4 105.8(2) . . ?
C6 C3 C4 102.8(3) . . ?
O2 C3 H3 111.9 . . ?
C6 C3 H3 111.9 . . ?
C4 C3 H3 111.9 . . ?
O4 C4 C1 111.3(2) . . ?
O4 C4 C3 105.9(2) . . ?
C1 C4 C3 103.4(3) . . ?
O4 C4 H4 111.9 . . ?
C1 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
O5 C5 O4 112.7(3) . . ?
O5 C5 C6 108.5(3) . . ?
O4 C5 C6 105.5(2) . . ?
O5 C5 H5 110.0 . . ?
O4 C5 H5 110.0 . . ?
C6 C5 H5 110.0 . . ?
O3 C6 C5 106.6(3) . . ?
O3 C6 C3 109.1(2) . . ?
C5 C6 C3 102.9(3) . . ?
O3 C6 H6 112.6 . . ?
C5 C6 H6 112.6 . . ?
C3 C6 H6 112.6 . . ?
O5 C7 C8 107.6(3) . . ?
O5 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O5 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C7 117.5(5) . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C8 C9 C10 111.4(6) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 O1 H1A 109.5 . . ?
C2 O2 C3 109.7(2) . . ?
C6 O3 H3A 109.5 . . ?
C5 O4 C4 110.8(2) . . ?
C5 O5 C7 114.3(2) . . ?

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 O2 -161.1(2) . . . . ?
C4 C1 C2 O2 -35.7(3) . . . . ?
O1 C1 C4 O4 47.8(4) . . . . ?
C2 C1 C4 O4 -77.7(3) . . . . ?
O1 C1 C4 C3 161.1(3) . . . . ?
C2 C1 C4 C3 35.6(3) . . . . ?
O2 C3 C4 O4 93.3(3) . . . . ?
C6 C3 C4 O4 -24.3(3) . . . . ?
O2 C3 C4 C1 -23.9(3) . . . . ?
C6 C3 C4 C1 -141.5(2) . . . . ?
O5 C5 C6 O3 -156.2(2) . . . . ?
O4 C5 C6 O3 82.8(3) . . . . ?
O5 C5 C6 C3 89.1(3) . . . . ?
O4 C5 C6 C3 -31.9(3) . . . . ?
O2 C3 C6 O3 167.8(2) . . . . ?
C4 C3 C6 O3 -79.1(3) . . . . ?
O2 C3 C6 C5 -79.3(3) . . . . ?
C4 C3 C6 C5 33.8(3) . . . . ?
O5 C7 C8 C9 56.0(6) . . . . ?
C7 C8 C9 C10 -176.0(5) . . . . ?
C1 C2 O2 C3 21.8(3) . . . . ?
C6 C3 O2 C2 112.8(3) . . . . ?
C4 C3 O2 C2 1.5(3) . . . . ?
O5 C5 O4 C4 -101.0(3) . . . . ?
C6 C5 O4 C4 17.2(3) . . . . ?
C1 C4 O4 C5 116.4(3) . . . . ?
C3 C4 O4 C5 4.7(3) . . . . ?
O4 C5 O5 C7 -71.6(3) . . . . ?
C6 C5 O5 C7 172.0(3) . . . . ?
C8 C7 O5 C5 -179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        64.99
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.096
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/AcOEt = 6/1'
