# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_a51230b
_database_code_depnum_ccdc_archive 'CCDC 1469830'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'N-(2,3,4-Tri-O-acetyl-6-deoxy-α-L-mannopyranos -1-yl) thiourea'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 N2 O7 S'
_chemical_formula_weight         348.37

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   8.984(5)
_cell_length_b                   10.648(6)
_cell_length_c                   18.894(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1807.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    881
_cell_measurement_theta_min      2.882
_cell_measurement_theta_max      25.228

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  -0.009
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8825
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         26.979
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3845
_reflns_number_gt                2450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.956
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0440P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3845
_refine_ls_number_parameters     224
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_restrained_S_all      0.843
_refine_ls_shift/su_max          0.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.06617(9) 1.17228(7) -0.07721(4) 0.0561(2) Uani 1 1 d . . . . .
N1 N 0.1421(3) 1.1593(2) 0.02365(13) 0.0509(6) Uani 1 1 d . . . . .
H1 H 0.222(3) 1.188(3) 0.0469(15) 0.054(9) Uiso 1 1 d . . . . .
N2 N 0.1461(4) 1.3324(3) -0.04513(16) 0.0665(8) Uani 1 1 d D . . . .
H2A H 0.111(4) 1.371(3) -0.0803(17) 0.091(13) Uiso 1 1 d D . . . .
H2B H 0.232(4) 1.355(3) -0.0244(16) 0.065(10) Uiso 1 1 d D . . . .
O1 O -0.0348(2) 1.05568(17) 0.09654(9) 0.0509(5) Uani 1 1 d . . . . .
O2 O 0.1609(2) 0.83467(16) 0.07740(11) 0.0561(5) Uani 1 1 d . . . . .
O3 O 0.3877(4) 0.7722(3) 0.04381(16) 0.1002(9) Uani 1 1 d . . . . .
O4 O 0.3330(2) 0.89936(19) 0.18869(11) 0.0587(5) Uani 1 1 d . . . . .
O5 O 0.5440(3) 0.9862(3) 0.15210(16) 0.0996(9) Uani 1 1 d . . . . .
O6 O 0.1576(3) 1.0630(2) 0.26678(11) 0.0716(7) Uani 1 1 d . . . . .
O7 O 0.0203(6) 0.9231(3) 0.32543(17) 0.1396(17) Uani 1 1 d . . . . .
C1 C 0.0845(3) 1.0412(2) 0.04927(14) 0.0471(7) Uani 1 1 d . . . . .
H1A H 0.0463 0.9956 0.0081 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2111(3) 0.9633(2) 0.07970(15) 0.0464(6) Uani 1 1 d . . . . .
H2 H 0.3002 0.9730 0.0503 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2471(3) 0.9981(3) 0.15617(14) 0.0481(7) Uani 1 1 d . . . . .
H3 H 0.3044 1.0764 0.1570 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1082(4) 1.0139(3) 0.19942(14) 0.0526(8) Uani 1 1 d . . . . .
H4 H 0.0575 0.9332 0.2057 0.063 Uiso 1 1 calc R U . . .
C5 C 0.0063(3) 1.1081(3) 0.16419(14) 0.0524(8) Uani 1 1 d . . . . .
H5 H 0.0595 1.1875 0.1571 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0810(3) 1.2251(3) -0.03021(14) 0.0496(7) Uani 1 1 d . . . . .
C7 C 0.2605(5) 0.7479(3) 0.0562(2) 0.0740(10) Uani 1 1 d . . . . .
C8 C 0.1914(5) 0.6213(3) 0.0525(3) 0.1199(19) Uani 1 1 d . . . . .
H8A H 0.2665 0.5601 0.0416 0.180 Uiso 1 1 calc R U . . .
H8B H 0.1166 0.6206 0.0162 0.180 Uiso 1 1 calc R U . . .
H8C H 0.1467 0.6013 0.0972 0.180 Uiso 1 1 calc R U . . .
C9 C 0.4815(4) 0.9058(4) 0.18312(18) 0.0670(9) Uani 1 1 d . . . . .
C10 C 0.5534(5) 0.7963(4) 0.2192(2) 0.1027(14) Uani 1 1 d . . . . .
H10A H 0.5416 0.7225 0.1906 0.154 Uiso 1 1 calc R U . . .
H10B H 0.5072 0.7830 0.2644 0.154 Uiso 1 1 calc R U . . .
H10C H 0.6574 0.8131 0.2258 0.154 Uiso 1 1 calc R U . . .
C11 C 0.1122(6) 1.0028(5) 0.3251(2) 0.0976(16) Uani 1 1 d . . . . .
C12 C 0.1938(7) 1.0532(6) 0.3881(2) 0.165(3) Uani 1 1 d . U . . .
H12A H 0.1621 1.0093 0.4298 0.247 Uiso 1 1 calc R U . . .
H12B H 0.1727 1.1412 0.3932 0.247 Uiso 1 1 calc R U . . .
H12C H 0.2988 1.0415 0.3816 0.247 Uiso 1 1 calc R U . . .
C13 C -0.1362(4) 1.1320(3) 0.20444(17) 0.0721(10) Uani 1 1 d . . . . .
H13A H -0.1964 1.1910 0.1788 0.108 Uiso 1 1 calc R U . . .
H13B H -0.1131 1.1656 0.2503 0.108 Uiso 1 1 calc R U . . .
H13C H -0.1898 1.0546 0.2098 0.108 Uiso 1 1 calc R U . . .


_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 C6 1.689(3) . ?
N1 C6 1.352(4) . ?
N1 C1 1.443(3) . ?
N1 H1 0.89(3) . ?
N2 C6 1.314(4) . ?
N2 H2A 0.84(3) . ?
N2 H2B 0.90(3) . ?
O1 C1 1.404(3) . ?
O1 C5 1.443(3) . ?
O2 C7 1.346(4) . ?
O2 C2 1.442(3) . ?
O3 C7 1.196(4) . ?
O4 C9 1.340(4) . ?
O4 C3 1.442(3) . ?
O5 C9 1.180(4) . ?
O6 C11 1.337(5) . ?
O6 C4 1.446(3) . ?
O7 C11 1.185(6) . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9800 . ?
C2 C3 1.526(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.501(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.513(4) . ?
C4 H4 0.9800 . ?
C5 C13 1.511(4) . ?
C5 H5 0.9800 . ?
C7 C8 1.486(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.497(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.497(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C6 N1 C1 123.9(3) . . ?
C6 N1 H1 121.0(18) . . ?
C1 N1 H1 115.1(18) . . ?
C6 N2 H2A 115(3) . . ?
C6 N2 H2B 121(2) . . ?
H2A N2 H2B 122(4) . . ?
C1 O1 C5 114.2(2) . . ?
C7 O2 C2 116.9(3) . . ?
C9 O4 C3 117.5(2) . . ?
C11 O6 C4 117.3(3) . . ?
O1 C1 N1 113.1(2) . . ?
O1 C1 C2 113.0(2) . . ?
N1 C1 C2 109.5(2) . . ?
O1 C1 H1A 107.0 . . ?
N1 C1 H1A 107.0 . . ?
C2 C1 H1A 107.0 . . ?
O2 C2 C1 105.8(2) . . ?
O2 C2 C3 109.0(2) . . ?
C1 C2 C3 112.6(2) . . ?
O2 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
O4 C3 C4 107.1(2) . . ?
O4 C3 C2 109.9(2) . . ?
C4 C3 C2 111.5(2) . . ?
O4 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
O6 C4 C3 105.3(3) . . ?
O6 C4 C5 109.5(2) . . ?
C3 C4 C5 109.8(2) . . ?
O6 C4 H4 110.7 . . ?
C3 C4 H4 110.7 . . ?
C5 C4 H4 110.7 . . ?
O1 C5 C13 107.1(2) . . ?
O1 C5 C4 106.7(2) . . ?
C13 C5 C4 113.8(2) . . ?
O1 C5 H5 109.7 . . ?
C13 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
N2 C6 N1 115.5(3) . . ?
N2 C6 S1 121.7(2) . . ?
N1 C6 S1 122.8(2) . . ?
O3 C7 O2 123.0(3) . . ?
O3 C7 C8 125.9(4) . . ?
O2 C7 C8 111.1(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 O4 123.3(3) . . ?
O5 C9 C10 125.9(4) . . ?
O4 C9 C10 110.7(3) . . ?
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 . . ?
O7 C11 O6 124.1(4) . . ?
O7 C11 C12 126.4(5) . . ?
O6 C11 C12 109.5(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C5 O1 C1 N1 -69.6(3) . . . . ?
C5 O1 C1 C2 55.5(3) . . . . ?
C6 N1 C1 O1 -82.0(3) . . . . ?
C6 N1 C1 C2 151.1(3) . . . . ?
C7 O2 C2 C1 137.8(3) . . . . ?
C7 O2 C2 C3 -100.9(3) . . . . ?
O1 C1 C2 O2 75.5(3) . . . . ?
N1 C1 C2 O2 -157.5(2) . . . . ?
O1 C1 C2 C3 -43.5(3) . . . . ?
N1 C1 C2 C3 83.5(3) . . . . ?
C9 O4 C3 C4 -149.3(3) . . . . ?
C9 O4 C3 C2 89.4(3) . . . . ?
O2 C2 C3 O4 45.6(3) . . . . ?
C1 C2 C3 O4 162.7(2) . . . . ?
O2 C2 C3 C4 -73.0(3) . . . . ?
C1 C2 C3 C4 44.1(3) . . . . ?
C11 O6 C4 C3 -127.9(3) . . . . ?
C11 O6 C4 C5 114.1(3) . . . . ?
O4 C3 C4 O6 67.4(3) . . . . ?
C2 C3 C4 O6 -172.4(2) . . . . ?
O4 C3 C4 C5 -174.8(2) . . . . ?
C2 C3 C4 C5 -54.6(3) . . . . ?
C1 O1 C5 C13 173.1(2) . . . . ?
C1 O1 C5 C4 -64.7(3) . . . . ?
O6 C4 C5 O1 178.1(2) . . . . ?
C3 C4 C5 O1 62.9(3) . . . . ?
O6 C4 C5 C13 -64.0(3) . . . . ?
C3 C4 C5 C13 -179.1(3) . . . . ?
C1 N1 C6 N2 178.2(3) . . . . ?
C1 N1 C6 S1 -3.4(4) . . . . ?
C2 O2 C7 O3 4.5(5) . . . . ?
C2 O2 C7 C8 -176.8(3) . . . . ?
C3 O4 C9 O5 -1.4(5) . . . . ?
C3 O4 C9 C10 -179.7(3) . . . . ?
C4 O6 C11 O7 -10.0(6) . . . . ?
C4 O6 C11 C12 170.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.89(3) 2.48(3) 3.333(3) 159(2) 4_575
N2 H2A O5 0.84(3) 2.12(3) 2.943(4) 164(4) 4_475
N2 H2B S1 0.90(3) 2.66(3) 3.468(4) 151(3) 4_575

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method dichloromethane/n-hexane
