# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_sl-20160929
_database_code_depnum_ccdc_archive 'CCDC 1510240'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H15 N O5 S'
_chemical_formula_sum            'C9 H15 N O5 S'
_chemical_formula_weight         249.28
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2179(3)
_cell_length_b                   10.0744(4)
_cell_length_c                   10.4155(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.042(5)
_cell_angle_gamma                90
_cell_volume                     623.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3602
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6480
_cell_measurement_theta_min      3.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5929
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_min         3.427
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  90.00   1.00   11.54    --   18.81  77.00 -60.00  103
  2  ω    -13.00  90.00   1.00   11.54    --   18.81  77.00-150.00  103
  3  ω    -50.00  40.00   1.00   11.54    --   18.81 -57.00-180.00   90
  4  ω     -3.00  88.00   1.00   11.54    --   18.81  57.00 120.00   91
  5  ω     34.00  97.00   1.00   11.54    --   18.81-178.00-180.00   63
  6  ω     34.00  97.00   1.00   11.54    --   18.81-178.00  90.00   63
  7  ω    -91.00 -49.00   1.00   11.54    --  -19.74 147.00 164.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382075000
_diffrn_orient_matrix_UB_12      0.0533425000
_diffrn_orient_matrix_UB_13      -0.0454312000
_diffrn_orient_matrix_UB_21      -0.0305277000
_diffrn_orient_matrix_UB_22      -0.0455711000
_diffrn_orient_matrix_UB_23      -0.0542362000
_diffrn_orient_matrix_UB_31      -0.1088475000
_diffrn_orient_matrix_UB_32      -0.0059505000
_diffrn_orient_matrix_UB_33      0.0082304000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2158
_reflns_number_total             2288
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.1008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 -1.05263(12) -0.43365(8) -0.56584(8) 0.0507(2) Uani 1 1 d . . . . .
O1 O -0.3615(6) -0.6478(3) -0.4299(3) 0.0746(9) Uani 1 1 d . . . . .
H1 H -0.272(8) -0.703(5) -0.423(5) 0.081(16) Uiso 1 1 d . . . . .
O2 O -0.5345(6) -0.7479(3) -0.6182(4) 0.1001(13) Uani 1 1 d . . . . .
O3 O -0.9911(4) -0.2955(2) -0.5949(3) 0.0700(8) Uani 1 1 d . . . . .
O4 O -0.5423(4) -0.4816(3) -0.8015(2) 0.0700(9) Uani 1 1 d . . . . .
O5 O -0.9091(4) -0.4892(3) -0.9262(2) 0.0610(7) Uani 1 1 d . . . . .
N1 N -0.8156(4) -0.5309(3) -0.7082(2) 0.0424(6) Uani 1 1 d . . . . .
C1 C -1.0481(5) -0.5319(4) -0.7099(3) 0.0464(7) Uani 1 1 d . . . . .
H1A H -1.0990 -0.6217 -0.7021 0.056 Uiso 1 1 calc R . . . .
H1B H -1.1431 -0.4927 -0.7921 0.056 Uiso 1 1 calc R . . . .
C2 C -0.7922(6) -0.5136(4) -0.4751(3) 0.0466(7) Uani 1 1 d . . . . .
H2A H -0.715(5) -0.457(4) -0.402(3) 0.052(9) Uiso 1 1 d . . . . .
H2B H -0.840(7) -0.595(5) -0.454(4) 0.075(13) Uiso 1 1 d . . . . .
C3 C -0.6562(5) -0.5306(3) -0.5742(3) 0.0379(6) Uani 1 1 d . . . . .
H3 H -0.5562 -0.4539 -0.5663 0.045 Uiso 1 1 calc R . . . .
C4 C -0.5135(5) -0.6561(3) -0.5463(3) 0.0441(7) Uani 1 1 d . . . . .
C5 C -0.7397(5) -0.4981(3) -0.8130(3) 0.0474(7) Uani 1 1 d . . . . .
C6 C -0.8669(8) -0.4701(4) -1.0581(3) 0.0695(11) Uani 1 1 d . . . . .
C7 C -0.7398(12) -0.5908(7) -1.0830(6) 0.108(2) Uani 1 1 d . . . . .
H7A H -0.5949 -0.5941 -1.0170 0.163 Uiso 1 1 calc GR . . . .
H7B H -0.7208 -0.5852 -1.1710 0.163 Uiso 1 1 calc GR . . . .
H7C H -0.8229 -0.6696 -1.0766 0.163 Uiso 1 1 calc GR . . . .
C8 C -0.7443(11) -0.3437(6) -1.0605(6) 0.1048(18) Uani 1 1 d . . . . .
H8A H -0.8266 -0.2713 -1.0378 0.157 Uiso 1 1 calc GR . . . .
H8B H -0.7295 -0.3299 -1.1487 0.157 Uiso 1 1 calc GR . . . .
H8C H -0.5976 -0.3484 -0.9966 0.157 Uiso 1 1 calc GR . . . .
C9 C -1.1026(10) -0.4663(7) -1.1516(4) 0.114(2) Uani 1 1 d . . . . .
H9A H -1.1779 -0.5480 -1.1447 0.172 Uiso 1 1 calc GR . . . .
H9B H -1.0976 -0.4549 -1.2422 0.172 Uiso 1 1 calc GR . . . .
H9C H -1.1828 -0.3935 -1.1277 0.172 Uiso 1 1 calc GR . . . .


_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 O3 1.497(3) . ?
S1 C1 1.805(3) . ?
S1 C2 1.807(4) . ?
O1 H1 0.78(5) . ?
O1 C4 1.303(4) . ?
O2 C4 1.172(4) . ?
O4 C5 1.210(4) . ?
O5 C5 1.334(4) . ?
O5 C6 1.485(4) . ?
N1 C1 1.440(4) . ?
N1 C3 1.456(4) . ?
N1 C5 1.351(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.96(4) . ?
C2 H2B 0.92(5) . ?
C2 C3 1.523(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.523(4) . ?
C6 C7 1.513(7) . ?
C6 C8 1.488(8) . ?
C6 C9 1.504(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O3 S1 C1 105.94(17) . . ?
O3 S1 C2 106.06(15) . . ?
C1 S1 C2 87.73(15) . . ?
C4 O1 H1 110(4) . . ?
C5 O5 C6 121.2(3) . . ?
C1 N1 C3 114.2(2) . . ?
C5 N1 C1 125.4(2) . . ?
C5 N1 C3 118.3(2) . . ?
S1 C1 H1A 110.9 . . ?
S1 C1 H1B 110.9 . . ?
N1 C1 S1 104.2(2) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
S1 C2 H2A 108(2) . . ?
S1 C2 H2B 102(3) . . ?
H2A C2 H2B 117(3) . . ?
C3 C2 S1 106.6(2) . . ?
C3 C2 H2A 111.1(19) . . ?
C3 C2 H2B 110(3) . . ?
N1 C3 C2 107.0(2) . . ?
N1 C3 H3 108.6 . . ?
N1 C3 C4 112.1(2) . . ?
C2 C3 H3 108.6 . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 H3 108.6 . . ?
O1 C4 C3 110.3(3) . . ?
O2 C4 O1 124.0(3) . . ?
O2 C4 C3 125.7(3) . . ?
O4 C5 O5 126.4(3) . . ?
O4 C5 N1 122.6(3) . . ?
O5 C5 N1 111.0(2) . . ?
O5 C6 C7 107.3(3) . . ?
O5 C6 C8 110.9(4) . . ?
O5 C6 C9 101.5(4) . . ?
C8 C6 C7 112.9(5) . . ?
C8 C6 C9 112.0(4) . . ?
C9 C6 C7 111.7(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
O1 H1 O3 0.78(5) 1.84(5) 2.600(4) 164(5) 2_444

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
S1 C2 C3 N1 -23.8(3) . . . . ?
S1 C2 C3 C4 -147.0(2) . . . . ?
O3 S1 C1 N1 65.5(2) . . . . ?
O3 S1 C2 C3 -68.6(3) . . . . ?
N1 C3 C4 O1 175.0(3) . . . . ?
N1 C3 C4 O2 -4.8(5) . . . . ?
C1 S1 C2 C3 37.4(2) . . . . ?
C1 N1 C3 C2 -7.2(4) . . . . ?
C1 N1 C3 C4 115.8(3) . . . . ?
C1 N1 C5 O4 169.8(3) . . . . ?
C1 N1 C5 O5 -11.0(5) . . . . ?
C2 S1 C1 N1 -40.6(2) . . . . ?
C2 C3 C4 O1 -64.7(4) . . . . ?
C2 C3 C4 O2 115.5(5) . . . . ?
C3 N1 C1 S1 34.7(3) . . . . ?
C3 N1 C5 O4 7.4(5) . . . . ?
C3 N1 C5 O5 -173.4(3) . . . . ?
C5 O5 C6 C7 62.7(5) . . . . ?
C5 O5 C6 C8 -60.9(5) . . . . ?
C5 O5 C6 C9 180.0(4) . . . . ?
C5 N1 C1 S1 -128.3(3) . . . . ?
C5 N1 C3 C2 157.1(3) . . . . ?
C5 N1 C3 C4 -79.9(3) . . . . ?
C6 O5 C5 O4 6.4(5) . . . . ?
C6 O5 C5 N1 -172.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.733
