# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1415387'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2?-N,4?-C-(Aminosulfonylmethylene)thymidine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N3 O7 S, H2 O'
_chemical_formula_sum            'C11 H17 N3 O8 S'
_chemical_formula_weight         351.34
_chemical_absolute_configuration rmad

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.49177(15)
_cell_length_b                   15.0859(3)
_cell_length_c                   7.43648(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.760(2)
_cell_angle_gamma                90.00
_cell_volume                     704.25(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7185
_cell_measurement_theta_min      5.87
_cell_measurement_theta_max      68.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    2.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
; 
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8240
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.87
_diffrn_reflns_theta_max         68.21
_reflns_number_total             2505
_reflns_number_gt                2420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID AUTO (Rigaku, 2010)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_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)+(0.0448P)²+0.1403P] 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   0.010(15)
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     221
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
S1 S -0.16543(7) 0.38216(3) 0.52908(7) 0.01335(12) Uani 1 1 d . . .
O1 O 0.3247(2) 0.27955(10) 0.7467(2) 0.0149(3) Uani 1 1 d . . .
H2 H 0.4212 0.2612 0.8370 0.018 Uiso 1 1 calc R . .
O2 O 0.3434(2) 0.59551(10) 0.3456(2) 0.0165(3) Uani 1 1 d . . .
O3 O 0.9369(2) 0.71248(10) 0.7337(2) 0.0199(4) Uani 1 1 d . . .
O4 O 0.1439(2) 0.50358(10) 0.78656(19) 0.0132(3) Uani 1 1 d . . .
O5 O 0.4189(2) 0.44284(11) 1.1324(2) 0.0221(4) Uani 1 1 d . . .
H12 H 0.4099 0.4871 1.1984 0.027 Uiso 1 1 calc R . .
O6 O -0.2521(2) 0.47009(10) 0.5005(2) 0.0173(3) Uani 1 1 d . . .
O7 O -0.3013(2) 0.30923(11) 0.4500(2) 0.0188(3) Uani 1 1 d . . .
O8W O 0.6535(3) 0.26902(12) 1.0516(2) 0.0253(4) Uani 1 1 d D . .
H16W H 0.762(3) 0.2369(18) 1.090(4) 0.030 Uiso 1 1 d D . .
H17W H 0.613(4) 0.2869(19) 1.138(3) 0.030 Uiso 1 1 d D . .
N1 N 0.4069(3) 0.56500(12) 0.6554(2) 0.0129(4) Uani 1 1 d . . .
N2 N 0.6316(3) 0.65802(12) 0.5476(2) 0.0133(4) Uani 1 1 d . . .
H5 H 0.6542 0.6914 0.4575 0.016 Uiso 1 1 calc R . .
N3 N 0.0452(2) 0.37681(13) 0.4482(2) 0.0123(3) Uani 1 1 d . . .
H15 H 0.056(4) 0.3274(19) 0.397(3) 0.015 Uiso 1 1 d . . .
C1 C 0.3181(3) 0.37321(15) 0.7507(3) 0.0128(4) Uani 1 1 d . . .
H1 H 0.4625 0.3963 0.8153 0.015 Uiso 1 1 calc R . .
C2 C 0.2460(3) 0.41619(14) 0.5603(3) 0.0126(4) Uani 1 1 d . . .
H3 H 0.3605 0.4138 0.4924 0.015 Uiso 1 1 calc R . .
C3 C 0.2091(3) 0.51189(14) 0.6182(3) 0.0125(4) Uani 1 1 d . . .
H4 H 0.0947 0.5410 0.5203 0.015 Uiso 1 1 calc R . .
C4 C 0.4532(3) 0.60566(14) 0.5045(3) 0.0131(4) Uani 1 1 d . . .
C5 C 0.7792(3) 0.66391(14) 0.7167(3) 0.0146(4) Uani 1 1 d . . .
C6 C 0.7311(3) 0.61306(13) 0.8655(3) 0.0135(4) Uani 1 1 d . . .
C7 C 0.8848(4) 0.61459(15) 1.0545(3) 0.0185(5) Uani 1 1 d . . .
H6 H 1.0280 0.6000 1.0430 0.022 Uiso 1 1 calc R . .
H7 H 0.8408 0.5709 1.1349 0.022 Uiso 1 1 calc R . .
H8 H 0.8858 0.6738 1.1089 0.022 Uiso 1 1 calc R . .
C8 C 0.5466(3) 0.56881(14) 0.8299(3) 0.0146(4) Uani 1 1 d . . .
H9 H 0.5098 0.5385 0.9294 0.018 Uiso 1 1 calc R . .
C9 C 0.1532(3) 0.41162(15) 0.8447(3) 0.0141(4) Uani 1 1 d . . .
C10 C 0.2132(3) 0.40792(15) 1.0557(3) 0.0175(5) Uani 1 1 d . . .
H10 H 0.1078 0.4420 1.1031 0.021 Uiso 1 1 calc R . .
H11 H 0.2086 0.3456 1.0962 0.021 Uiso 1 1 calc R . .
C11 C -0.0657(3) 0.36717(14) 0.7728(3) 0.0152(4) Uani 1 1 d . . .
H13 H -0.1674 0.3929 0.8376 0.018 Uiso 1 1 calc R . .
H14 H -0.0528 0.3030 0.8013 0.018 Uiso 1 1 calc R . .


_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 O6 1.4354(16) . ?
S1 O7 1.4387(16) . ?
S1 N3 1.6299(16) . ?
S1 C11 1.777(2) . ?
O1 C1 1.414(3) . ?
O1 H2 0.8400 . ?
O2 C4 1.225(3) . ?
O3 C5 1.239(3) . ?
O4 C3 1.425(2) . ?
O4 C9 1.450(3) . ?
O5 C10 1.413(3) . ?
O5 H12 0.8400 . ?
O8W H16W 0.840(17) . ?
O8W H17W 0.801(17) . ?
N1 C4 1.378(3) . ?
N1 C8 1.382(3) . ?
N1 C3 1.478(3) . ?
N2 C4 1.371(3) . ?
N2 C5 1.376(3) . ?
N2 H5 0.8800 . ?
N3 C2 1.481(3) . ?
N3 H15 0.85(3) . ?
C1 C2 1.519(3) . ?
C1 C9 1.534(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.543(3) . ?
C2 H3 1.0000 . ?
C3 H4 1.0000 . ?
C5 C6 1.444(3) . ?
C6 C8 1.338(3) . ?
C6 C7 1.502(3) . ?
C7 H6 0.9800 . ?
C7 H7 0.9800 . ?
C7 H8 0.9800 . ?
C8 H9 0.9500 . ?
C9 C10 1.518(3) . ?
C9 C11 1.538(3) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?

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
O6 S1 O7 118.02(9) . . ?
O6 S1 N3 108.96(9) . . ?
O7 S1 N3 107.23(10) . . ?
O6 S1 C11 107.20(10) . . ?
O7 S1 C11 110.22(10) . . ?
N3 S1 C11 104.36(9) . . ?
C1 O1 H2 109.5 . . ?
C3 O4 C9 110.30(15) . . ?
C10 O5 H12 109.5 . . ?
H16W O8W H17W 110(3) . . ?
C4 N1 C8 121.27(18) . . ?
C4 N1 C3 116.63(16) . . ?
C8 N1 C3 121.94(17) . . ?
C4 N2 C5 126.92(18) . . ?
C4 N2 H5 116.5 . . ?
C5 N2 H5 116.5 . . ?
C2 N3 S1 118.26(14) . . ?
C2 N3 H15 116.3(17) . . ?
S1 N3 H15 112.5(17) . . ?
O1 C1 C2 114.24(17) . . ?
O1 C1 C9 114.55(17) . . ?
C2 C1 C9 100.27(17) . . ?
O1 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C9 C1 H1 109.1 . . ?
N3 C2 C1 111.81(17) . . ?
N3 C2 C3 110.84(17) . . ?
C1 C2 C3 99.90(16) . . ?
N3 C2 H3 111.3 . . ?
C1 C2 H3 111.3 . . ?
C3 C2 H3 111.3 . . ?
O4 C3 N1 108.75(16) . . ?
O4 C3 C2 105.36(16) . . ?
N1 C3 C2 111.74(17) . . ?
O4 C3 H4 110.3 . . ?
N1 C3 H4 110.3 . . ?
C2 C3 H4 110.3 . . ?
O2 C4 N2 123.14(18) . . ?
O2 C4 N1 122.46(19) . . ?
N2 C4 N1 114.40(17) . . ?
O3 C5 N2 119.75(19) . . ?
O3 C5 C6 124.8(2) . . ?
N2 C5 C6 115.46(19) . . ?
C8 C6 C5 118.10(19) . . ?
C8 C6 C7 122.7(2) . . ?
C5 C6 C7 119.15(19) . . ?
C6 C7 H6 109.5 . . ?
C6 C7 H7 109.5 . . ?
H6 C7 H7 109.5 . . ?
C6 C7 H8 109.5 . . ?
H6 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
C6 C8 N1 123.15(19) . . ?
C6 C8 H9 118.4 . . ?
N1 C8 H9 118.4 . . ?
O4 C9 C10 108.87(17) . . ?
O4 C9 C1 101.91(16) . . ?
C10 C9 C1 115.58(18) . . ?
O4 C9 C11 110.43(17) . . ?
C10 C9 C11 108.31(17) . . ?
C1 C9 C11 111.55(17) . . ?
O5 C10 C9 111.75(17) . . ?
O5 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
O5 C10 H11 109.3 . . ?
C9 C10 H11 109.3 . . ?
H10 C10 H11 107.9 . . ?
C9 C11 S1 111.30(14) . . ?
C9 C11 H13 109.4 . . ?
S1 C11 H13 109.4 . . ?
C9 C11 H14 109.4 . . ?
S1 C11 H14 109.4 . . ?
H13 C11 H14 108.0 . . ?

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
O6 S1 N3 C2 77.11(17) . . . . ?
O7 S1 N3 C2 -154.07(16) . . . . ?
C11 S1 N3 C2 -37.14(18) . . . . ?
S1 N3 C2 C1 59.9(2) . . . . ?
S1 N3 C2 C3 -50.6(2) . . . . ?
O1 C1 C2 N3 50.5(2) . . . . ?
C9 C1 C2 N3 -72.5(2) . . . . ?
O1 C1 C2 C3 167.84(16) . . . . ?
C9 C1 C2 C3 44.83(19) . . . . ?
C9 O4 C3 N1 -115.57(18) . . . . ?
C9 O4 C3 C2 4.4(2) . . . . ?
C4 N1 C3 O4 -158.16(17) . . . . ?
C8 N1 C3 O4 26.3(3) . . . . ?
C4 N1 C3 C2 86.0(2) . . . . ?
C8 N1 C3 C2 -89.6(2) . . . . ?
N3 C2 C3 O4 86.75(19) . . . . ?
C1 C2 C3 O4 -31.3(2) . . . . ?
N3 C2 C3 N1 -155.32(16) . . . . ?
C1 C2 C3 N1 86.65(18) . . . . ?
C5 N2 C4 O2 -170.6(2) . . . . ?
C5 N2 C4 N1 9.4(3) . . . . ?
C8 N1 C4 O2 172.08(18) . . . . ?
C3 N1 C4 O2 -3.5(3) . . . . ?
C8 N1 C4 N2 -7.9(3) . . . . ?
C3 N1 C4 N2 176.57(16) . . . . ?
C4 N2 C5 O3 177.9(2) . . . . ?
C4 N2 C5 C6 -4.0(3) . . . . ?
O3 C5 C6 C8 175.0(2) . . . . ?
N2 C5 C6 C8 -3.0(3) . . . . ?
O3 C5 C6 C7 -2.8(3) . . . . ?
N2 C5 C6 C7 179.22(18) . . . . ?
C5 C6 C8 N1 4.2(3) . . . . ?
C7 C6 C8 N1 -178.17(19) . . . . ?
C4 N1 C8 C6 1.6(3) . . . . ?
C3 N1 C8 C6 176.9(2) . . . . ?
C3 O4 C9 C10 146.85(16) . . . . ?
C3 O4 C9 C1 24.3(2) . . . . ?
C3 O4 C9 C11 -94.36(19) . . . . ?
O1 C1 C9 O4 -165.92(16) . . . . ?
C2 C1 C9 O4 -43.13(19) . . . . ?
O1 C1 C9 C10 76.2(2) . . . . ?
C2 C1 C9 C10 -161.00(18) . . . . ?
O1 C1 C9 C11 -48.1(2) . . . . ?
C2 C1 C9 C11 74.7(2) . . . . ?
O4 C9 C10 O5 -63.4(2) . . . . ?
C1 C9 C10 O5 50.5(2) . . . . ?
C11 C9 C10 O5 176.46(17) . . . . ?
O4 C9 C11 S1 52.69(19) . . . . ?
C10 C9 C11 S1 171.82(14) . . . . ?
C1 C9 C11 S1 -59.9(2) . . . . ?
O6 S1 C11 C9 -79.22(16) . . . . ?
O7 S1 C11 C9 151.13(14) . . . . ?
N3 S1 C11 C9 36.28(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.049



