# 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_cd16566
_database_code_depnum_ccdc_archive 'CCDC 1508194'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2016-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O4 S'
_chemical_formula_weight         301.31

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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.8402(18)
_cell_length_b                   10.9776(18)
_cell_length_c                   11.4168(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1358.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3274
_cell_measurement_theta_min      5.148
_cell_measurement_theta_max      51.846

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6641
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            7834
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2529
_reflns_number_gt                2352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0511P)²+0.1165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0868
_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_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 -0.02344(7) 0.67889(7) 0.02443(6) 0.0373(2) Uani 1 1 d . . . . .
N1 N 0.0640(2) 0.7210(2) 0.1429(2) 0.0353(6) Uani 1 1 d . . . . .
O1 O 0.2069(2) 0.8700(2) 0.1886(2) 0.0520(6) Uani 1 1 d . . . . .
O2 O 0.0564(2) 0.5283(2) 0.21043(18) 0.0529(6) Uani 1 1 d . . . . .
O3 O -0.1453(2) 0.6558(2) 0.0620(2) 0.0571(7) Uani 1 1 d . . . . .
O4 O 0.0397(2) 0.5899(2) -0.04263(19) 0.0557(7) Uani 1 1 d . . . . .
C1 C -0.0062(2) 0.8209(3) -0.0412(2) 0.0355(6) Uani 1 1 d . . . . .
C2 C -0.0584(3) 0.8581(3) -0.1454(3) 0.0486(8) Uani 1 1 d . . . . .
H2 H -0.1146 0.8093 -0.1852 0.058 Uiso 1 1 calc R U . . .
C3 C -0.0242(4) 0.9697(4) -0.1880(3) 0.0594(10) Uani 1 1 d . . . . .
H3 H -0.0577 0.9975 -0.2581 0.071 Uiso 1 1 calc R U . . .
C4 C 0.0596(4) 1.0417(4) -0.1282(4) 0.0605(10) Uani 1 1 d . . . . .
H4 H 0.0818 1.1170 -0.1591 0.073 Uiso 1 1 calc R U . . .
C5 C 0.1106(3) 1.0039(3) -0.0240(3) 0.0509(8) Uani 1 1 d . . . . .
H5 H 0.1665 1.0529 0.0161 0.061 Uiso 1 1 calc R U . . .
C6 C 0.0768(3) 0.8921(3) 0.0193(3) 0.0368(6) Uani 1 1 d . . . . .
C7 C 0.1264(3) 0.8339(3) 0.1264(2) 0.0362(7) Uani 1 1 d . . . . .
C8 C 0.0813(3) 0.6327(3) 0.2322(2) 0.0367(7) Uani 1 1 d . . . . .
C9 C 0.1253(2) 0.6736(3) 0.3484(2) 0.0332(6) Uani 1 1 d . . . . .
C10 C 0.2032(3) 0.5957(3) 0.4088(3) 0.0395(7) Uani 1 1 d . . . . .
H10 H 0.2296 0.5236 0.3742 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2415(3) 0.6255(3) 0.5204(3) 0.0434(7) Uani 1 1 d . . . . .
H11 H 0.2967 0.5747 0.5592 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1993(3) 0.7294(3) 0.5757(3) 0.0393(7) Uani 1 1 d . . . . .
C13 C 0.1199(3) 0.8054(3) 0.5154(3) 0.0392(7) Uani 1 1 d . . . . .
H13 H 0.0899 0.8752 0.5519 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0842(3) 0.7795(3) 0.4015(3) 0.0376(7) Uani 1 1 d . . . . .
H14 H 0.0330 0.8328 0.3610 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2387(4) 0.7592(4) 0.6987(3) 0.0596(10) Uani 1 1 d . . . . .
H15A H 0.1764 0.7324 0.7527 0.089 Uiso 1 1 calc R U . . .
H15B H 0.2499 0.8456 0.7062 0.089 Uiso 1 1 calc R U . . .
H15C H 0.3150 0.7184 0.7158 0.089 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 O3 1.412(2) . ?
S1 O4 1.418(2) . ?
S1 N1 1.715(2) . ?
S1 C1 1.740(3) . ?
N1 C8 1.419(4) . ?
N1 C7 1.425(4) . ?
O1 C7 1.192(4) . ?
O2 C8 1.203(4) . ?
C1 C6 1.378(4) . ?
C1 C2 1.379(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(4) . ?
C8 C9 1.479(4) . ?
C9 C14 1.385(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 C15 1.504(5) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 O4 119.49(16) . . ?
O3 S1 N1 109.03(13) . . ?
O4 S1 N1 110.17(14) . . ?
O3 S1 C1 113.05(15) . . ?
O4 S1 C1 109.47(14) . . ?
N1 S1 C1 92.24(12) . . ?
C8 N1 C7 128.8(2) . . ?
C8 N1 S1 117.12(19) . . ?
C7 N1 S1 113.10(19) . . ?
C6 C1 C2 122.2(3) . . ?
C6 C1 S1 111.2(2) . . ?
C2 C1 S1 126.4(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 125.9(3) . . ?
C1 C6 C7 114.0(3) . . ?
O1 C7 N1 123.9(3) . . ?
O1 C7 C6 127.9(3) . . ?
N1 C7 C6 108.2(2) . . ?
O2 C8 N1 118.2(3) . . ?
O2 C8 C9 123.1(3) . . ?
N1 C8 C9 118.7(2) . . ?
C14 C9 C10 119.8(3) . . ?
C14 C9 C8 122.9(3) . . ?
C10 C9 C8 117.1(3) . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 C15 120.7(3) . . ?
C11 C12 C15 120.7(3) . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 119.5(3) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O3 S1 N1 C8 64.3(3) . . . . ?
O4 S1 N1 C8 -68.7(2) . . . . ?
C1 S1 N1 C8 179.6(2) . . . . ?
O3 S1 N1 C7 -126.1(2) . . . . ?
O4 S1 N1 C7 100.9(2) . . . . ?
C1 S1 N1 C7 -10.8(2) . . . . ?
O3 S1 C1 C6 119.3(2) . . . . ?
O4 S1 C1 C6 -104.9(2) . . . . ?
N1 S1 C1 C6 7.5(2) . . . . ?
O3 S1 C1 C2 -66.0(3) . . . . ?
O4 S1 C1 C2 69.8(3) . . . . ?
N1 S1 C1 C2 -177.8(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
S1 C1 C2 C3 -173.9(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
S1 C1 C6 C5 174.7(2) . . . . ?
C2 C1 C6 C7 -177.4(3) . . . . ?
S1 C1 C6 C7 -2.5(3) . . . . ?
C8 N1 C7 O1 0.9(5) . . . . ?
S1 N1 C7 O1 -167.2(3) . . . . ?
C8 N1 C7 C6 178.9(3) . . . . ?
S1 N1 C7 C6 10.8(3) . . . . ?
C5 C6 C7 O1 -4.3(5) . . . . ?
C1 C6 C7 O1 172.7(3) . . . . ?
C5 C6 C7 N1 177.8(3) . . . . ?
C1 C6 C7 N1 -5.2(3) . . . . ?
C7 N1 C8 O2 -152.9(3) . . . . ?
S1 N1 C8 O2 14.8(4) . . . . ?
C7 N1 C8 C9 28.9(4) . . . . ?
S1 N1 C8 C9 -163.4(2) . . . . ?
O2 C8 C9 C14 -137.8(3) . . . . ?
N1 C8 C9 C14 40.3(4) . . . . ?
O2 C8 C9 C10 36.7(4) . . . . ?
N1 C8 C9 C10 -145.2(3) . . . . ?
C14 C9 C10 C11 -1.4(4) . . . . ?
C8 C9 C10 C11 -176.2(3) . . . . ?
C9 C10 C11 C12 2.9(5) . . . . ?
C10 C11 C12 C13 -1.7(5) . . . . ?
C10 C11 C12 C15 178.2(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C15 C12 C13 C14 179.2(3) . . . . ?
C10 C9 C14 C13 -1.1(4) . . . . ?
C8 C9 C14 C13 173.4(3) . . . . ?
C12 C13 C14 C9 2.2(5) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

