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

#######################################################################
#
#                 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_20131022lt_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O6 S'
_chemical_formula_weight         287.28

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'

_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                   5.3793(2)
_cell_length_b                   13.1499(5)
_cell_length_c                   17.4076(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1231.37(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.46

_exptl_crystal_description       Block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9319
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34700
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.47
_reflns_number_total             3107
_reflns_number_gt                3041
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0436P)²+0.4957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_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   -0.01(6)
_refine_ls_number_reflns         3107
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.22766(6) 0.22986(2) 0.408472(18) 0.01271(8) Uani 1 1 d . . .
O1 O 0.0814(2) 0.15485(8) 0.44745(6) 0.0193(2) Uani 1 1 d . . .
O2 O 0.48816(19) 0.20959(8) 0.40420(6) 0.0193(2) Uani 1 1 d . . .
O3 O 0.11479(19) 0.24399(7) 0.32506(5) 0.0139(2) Uani 1 1 d . . .
O4 O -0.0288(2) 0.82261(8) 0.38642(6) 0.0186(2) Uani 1 1 d . . .
O5 O 0.4417(2) 0.37568(9) 0.26213(7) 0.0190(2) Uani 1 1 d . . .
O6 O 0.1312(2) 0.48398(8) 0.23286(6) 0.0159(2) Uani 1 1 d . . .
N1 N 0.1776(2) 0.34614(9) 0.43695(7) 0.0138(2) Uani 1 1 d . . .
H1B H 0.2598 0.3772 0.4738 0.017 Uiso 1 1 calc R . .
C1 C 0.1707(3) 0.56007(11) 0.43045(8) 0.0153(3) Uani 1 1 d . . .
H1C H 0.3016 0.5240 0.4550 0.018 Uiso 1 1 calc R . .
C2 C 0.1745(3) 0.66691(11) 0.42960(8) 0.0156(3) Uani 1 1 d . . .
H2B H 0.3056 0.7030 0.4540 0.019 Uiso 1 1 calc R . .
C3 C -0.0159(3) 0.71912(11) 0.39267(7) 0.0139(3) Uani 1 1 d . . .
C4 C 0.1761(3) 0.88033(11) 0.41589(10) 0.0210(3) Uani 1 1 d . . .
H4A H 0.1449 0.9530 0.4078 0.031 Uiso 1 1 calc R . .
H4B H 0.3288 0.8606 0.3890 0.031 Uiso 1 1 calc R . .
H4C H 0.1948 0.8669 0.4710 0.031 Uiso 1 1 calc R . .
C5 C -0.2116(3) 0.66583(10) 0.35894(8) 0.0154(3) Uani 1 1 d . . .
H5A H -0.3425 0.7017 0.3342 0.018 Uiso 1 1 calc R . .
C6 C -0.2150(3) 0.56051(11) 0.36153(8) 0.0148(3) Uani 1 1 d . . .
H6A H -0.3507 0.5246 0.3396 0.018 Uiso 1 1 calc R . .
C7 C -0.0209(2) 0.50654(10) 0.39611(7) 0.0122(2) Uani 1 1 d . . .
C8 C -0.0250(3) 0.39135(10) 0.39187(7) 0.0125(3) Uani 1 1 d . . .
H8A H -0.1884 0.3655 0.4111 0.015 Uiso 1 1 calc R . .
C9 C 0.0282(3) 0.34667(10) 0.31103(7) 0.0120(2) Uani 1 1 d . . .
H9A H -0.1291 0.3446 0.2804 0.014 Uiso 1 1 calc R . .
C10 C 0.2284(3) 0.40256(10) 0.26593(7) 0.0128(2) Uani 1 1 d . . .
C11 C 0.3009(3) 0.54589(12) 0.18840(9) 0.0213(3) Uani 1 1 d . . .
H11A H 0.2108 0.6038 0.1665 0.032 Uiso 1 1 calc R . .
H11B H 0.3724 0.5050 0.1469 0.032 Uiso 1 1 calc R . .
H11C H 0.4344 0.5708 0.2218 0.032 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 0.01596(15) 0.01087(14) 0.01131(13) -0.00009(10) -0.00028(12) 0.00196(12)
O1 0.0274(6) 0.0138(5) 0.0166(5) 0.0025(4) 0.0037(4) -0.0004(4)
O2 0.0163(5) 0.0231(5) 0.0186(5) -0.0038(4) -0.0018(4) 0.0063(4)
O3 0.0191(5) 0.0110(5) 0.0118(4) -0.0002(3) -0.0021(4) 0.0009(4)
O4 0.0212(5) 0.0112(5) 0.0232(5) 0.0013(4) -0.0047(4) -0.0013(4)
O5 0.0123(5) 0.0220(5) 0.0227(5) 0.0051(4) -0.0004(4) 0.0004(4)
O6 0.0165(5) 0.0145(5) 0.0167(4) 0.0044(4) 0.0036(4) 0.0010(4)
N1 0.0190(6) 0.0103(5) 0.0122(5) -0.0014(4) -0.0035(4) 0.0028(4)
C1 0.0140(6) 0.0144(6) 0.0173(6) 0.0002(5) -0.0017(5) 0.0011(5)
C2 0.0131(6) 0.0143(6) 0.0194(6) -0.0006(5) -0.0021(5) -0.0012(5)
C3 0.0159(6) 0.0118(6) 0.0142(6) 0.0005(5) 0.0030(5) 0.0008(5)
C4 0.0235(7) 0.0137(6) 0.0256(7) -0.0006(6) -0.0020(6) -0.0041(5)
C5 0.0152(6) 0.0147(6) 0.0163(6) 0.0011(5) -0.0017(5) 0.0025(5)
C6 0.0136(6) 0.0153(6) 0.0156(6) -0.0006(5) -0.0011(5) -0.0008(5)
C7 0.0120(6) 0.0127(6) 0.0120(6) -0.0001(4) 0.0020(5) 0.0003(5)
C8 0.0131(6) 0.0126(6) 0.0119(6) 0.0007(4) -0.0003(5) 0.0007(5)
C9 0.0122(6) 0.0107(6) 0.0130(6) 0.0009(5) -0.0012(5) -0.0002(5)
C10 0.0146(6) 0.0134(6) 0.0105(5) -0.0008(4) -0.0017(5) -0.0018(5)
C11 0.0201(7) 0.0209(7) 0.0228(7) 0.0101(6) 0.0036(6) -0.0021(6)

_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 O2 1.4283(11) . ?
S1 O1 1.4328(11) . ?
S1 O3 1.5847(10) . ?
S1 N1 1.6297(12) . ?
O3 C9 1.4491(15) . ?
O4 C3 1.3670(16) . ?
O4 C4 1.4334(18) . ?
O5 C10 1.2025(18) . ?
O6 C10 1.3234(17) . ?
O6 C11 1.4475(17) . ?
N1 C8 1.4690(17) . ?
N1 H1B 0.8800 . ?
C1 C7 1.3839(19) . ?
C1 C2 1.4052(19) . ?
C1 H1C 0.9500 . ?
C2 C3 1.3908(19) . ?
C2 H2B 0.9500 . ?
C3 C5 1.394(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.3859(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3986(19) . ?
C6 H6A 0.9500 . ?
C7 C8 1.5166(18) . ?
C8 C9 1.5516(18) . ?
C8 H8A 1.0000 . ?
C9 C10 1.5221(19) . ?
C9 H9A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
O2 S1 O1 115.79(7) . . ?
O2 S1 O3 110.49(6) . . ?
O1 S1 O3 107.71(6) . . ?
O2 S1 N1 110.67(7) . . ?
O1 S1 N1 114.27(6) . . ?
O3 S1 N1 96.05(6) . . ?
C9 O3 S1 112.76(8) . . ?
C3 O4 C4 117.37(12) . . ?
C10 O6 C11 116.00(12) . . ?
C8 N1 S1 109.87(9) . . ?
C8 N1 H1B 125.1 . . ?
S1 N1 H1B 125.1 . . ?
C7 C1 C2 121.00(13) . . ?
C7 C1 H1C 119.5 . . ?
C2 C1 H1C 119.5 . . ?
C3 C2 C1 119.18(13) . . ?
C3 C2 H2B 120.4 . . ?
C1 C2 H2B 120.4 . . ?
O4 C3 C2 124.44(13) . . ?
O4 C3 C5 115.37(13) . . ?
C2 C3 C5 120.19(13) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 119.90(13) . . ?
C6 C5 H5A 120.1 . . ?
C3 C5 H5A 120.1 . . ?
C5 C6 C7 120.75(13) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C1 C7 C6 118.93(13) . . ?
C1 C7 C8 122.68(12) . . ?
C6 C7 C8 118.36(12) . . ?
N1 C8 C7 111.56(11) . . ?
N1 C8 C9 101.21(10) . . ?
C7 C8 C9 114.81(11) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O3 C9 C10 108.02(11) . . ?
O3 C9 C8 105.02(10) . . ?
C10 C9 C8 114.55(11) . . ?
O3 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O5 C10 O6 126.23(13) . . ?
O5 C10 C9 124.17(12) . . ?
O6 C10 C9 109.59(12) . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O2 S1 O3 C9 -113.55(9) . . . . ?
O1 S1 O3 C9 119.09(9) . . . . ?
N1 S1 O3 C9 1.19(9) . . . . ?
O2 S1 N1 C8 138.18(9) . . . . ?
O1 S1 N1 C8 -88.96(10) . . . . ?
O3 S1 N1 C8 23.59(10) . . . . ?
C7 C1 C2 C3 -0.9(2) . . . . ?
C4 O4 C3 C2 4.0(2) . . . . ?
C4 O4 C3 C5 -176.10(12) . . . . ?
C1 C2 C3 O4 -178.28(13) . . . . ?
C1 C2 C3 C5 1.9(2) . . . . ?
O4 C3 C5 C6 179.45(13) . . . . ?
C2 C3 C5 C6 -0.7(2) . . . . ?
C3 C5 C6 C7 -1.5(2) . . . . ?
C2 C1 C7 C6 -1.2(2) . . . . ?
C2 C1 C7 C8 176.53(13) . . . . ?
C5 C6 C7 C1 2.5(2) . . . . ?
C5 C6 C7 C8 -175.42(12) . . . . ?
S1 N1 C8 C7 -160.49(9) . . . . ?
S1 N1 C8 C9 -37.93(12) . . . . ?
C1 C7 C8 N1 7.62(18) . . . . ?
C6 C7 C8 N1 -174.60(12) . . . . ?
C1 C7 C8 C9 -106.77(15) . . . . ?
C6 C7 C8 C9 71.02(16) . . . . ?
S1 O3 C9 C10 99.08(10) . . . . ?
S1 O3 C9 C8 -23.59(12) . . . . ?
N1 C8 C9 O3 37.04(12) . . . . ?
C7 C8 C9 O3 157.32(11) . . . . ?
N1 C8 C9 C10 -81.30(13) . . . . ?
C7 C8 C9 C10 38.98(16) . . . . ?
C11 O6 C10 O5 -0.3(2) . . . . ?
C11 O6 C10 C9 179.30(11) . . . . ?
O3 C9 C10 O5 -18.70(18) . . . . ?
C8 C9 C10 O5 97.93(16) . . . . ?
O3 C9 C10 O6 161.69(10) . . . . ?
C8 C9 C10 O6 -81.68(14) . . . . ?

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 H1B O1 0.88 2.25 2.9607(16) 138.1 4_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1007235'
