# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cd17139
_database_code_depnum_ccdc_archive 'CCDC 1586853'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O4 S'
_chemical_formula_weight         342.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.6656(16)
_cell_length_b                   19.475(4)
_cell_length_c                   10.707(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.755(4)
_cell_angle_gamma                90
_cell_volume                     1595.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      4.348
_cell_measurement_theta_max      49.689

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6058
_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            8635
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.091
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2804
_reflns_number_gt                2245
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.0594P)²+0.6680P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.22229(8) 0.32716(4) 0.70747(6) 0.0515(2) Uani 1 1 d . . . . .
N1 N 0.4827(2) 0.35733(10) 0.57864(17) 0.0410(5) Uani 1 1 d . . . . .
N2 N 0.2743(3) 0.18936(13) 0.5697(2) 0.0626(6) Uani 1 1 d . . . . .
O1 O 0.2019(2) 0.46988(10) 0.50879(17) 0.0621(5) Uani 1 1 d . . . . .
O2 O 0.0209(2) 0.47017(12) 0.66274(18) 0.0680(6) Uani 1 1 d . . . . .
H2 H -0.0442 0.4900 0.6106 0.102 Uiso 1 1 calc R U . . .
O3 O 0.1630(3) 0.19840(12) 0.6470(2) 0.0829(7) Uani 1 1 d . . . . .
O4 O 0.2935(3) 0.13335(11) 0.5190(3) 0.0907(7) Uani 1 1 d . . . . .
C1 C 0.2923(3) 0.41737(13) 0.7045(2) 0.0468(6) Uani 1 1 d . . . . .
H1 H 0.2903 0.4374 0.7883 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4784(3) 0.41607(12) 0.6634(2) 0.0416(5) Uani 1 1 d . . . . .
H2A H 0.4993 0.4581 0.6163 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3724(3) 0.30536(13) 0.5995(2) 0.0418(5) Uani 1 1 d . . . . .
C4 C 0.3830(3) 0.24291(13) 0.5431(2) 0.0509(6) Uani 1 1 d . . . . .
H4A H 0.4662 0.2363 0.4849 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1678(3) 0.45576(13) 0.6141(2) 0.0493(6) Uani 1 1 d . . . . .
C6 C 0.6123(3) 0.41176(12) 0.7739(2) 0.0402(5) Uani 1 1 d . . . . .
C7 C 0.6576(3) 0.47164(13) 0.8367(2) 0.0540(7) Uani 1 1 d . . . . .
H7 H 0.6066 0.5129 0.8103 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7775(4) 0.47094(16) 0.9382(3) 0.0629(7) Uani 1 1 d . . . . .
H8 H 0.8057 0.5114 0.9809 0.075 Uiso 1 1 calc R U . . .
C9 C 0.8546(4) 0.41099(17) 0.9758(3) 0.0631(8) Uani 1 1 d . . . . .
H9 H 0.9380 0.4107 1.0429 0.076 Uiso 1 1 calc R U . . .
C10 C 0.8102(3) 0.35140(15) 0.9157(3) 0.0595(7) Uani 1 1 d . . . . .
H10 H 0.8625 0.3104 0.9427 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6876(3) 0.35124(13) 0.8147(2) 0.0503(6) Uani 1 1 d . . . . .
H11 H 0.6566 0.3102 0.7747 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6009(3) 0.35509(11) 0.4804(2) 0.0398(5) Uani 1 1 d . . . . .
C13 C 0.7755(3) 0.34081(15) 0.5059(3) 0.0577(7) Uani 1 1 d . . . . .
H13 H 0.8195 0.3327 0.5876 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8840(4) 0.33874(17) 0.4084(3) 0.0680(8) Uani 1 1 d . . . . .
H14 H 1.0021 0.3291 0.4248 0.082 Uiso 1 1 calc R U . . .
C15 C 0.8212(4) 0.35058(16) 0.2885(3) 0.0659(8) Uani 1 1 d . . . . .
H15 H 0.8959 0.3490 0.2236 0.079 Uiso 1 1 calc R U . . .
C16 C 0.6468(4) 0.36490(17) 0.2639(3) 0.0664(8) Uani 1 1 d . . . . .
H16 H 0.6032 0.3731 0.1821 0.080 Uiso 1 1 calc R U . . .
C17 C 0.5367(3) 0.36710(14) 0.3602(2) 0.0541(7) Uani 1 1 d . . . . .
H17 H 0.4186 0.3767 0.3435 0.065 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 C3 1.737(2) . ?
S1 C1 1.838(3) . ?
N1 C3 1.347(3) . ?
N1 C12 1.433(3) . ?
N1 C2 1.462(3) . ?
N2 O4 1.232(3) . ?
N2 O3 1.239(3) . ?
N2 C4 1.376(3) . ?
O1 C5 1.206(3) . ?
O2 C5 1.302(3) . ?
O2 H2 0.8200 . ?
C1 C5 1.511(3) . ?
C1 C2 1.521(3) . ?
C1 H1 0.9800 . ?
C2 C6 1.517(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.362(3) . ?
C4 H4A 0.9300 . ?
C6 C11 1.371(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.359(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.368(3) . ?
C12 C13 1.377(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C3 S1 C1 90.87(11) . . ?
C3 N1 C12 122.17(19) . . ?
C3 N1 C2 116.46(19) . . ?
C12 N1 C2 121.36(18) . . ?
O4 N2 O3 121.8(2) . . ?
O4 N2 C4 119.2(3) . . ?
O3 N2 C4 118.9(3) . . ?
C5 O2 H2 109.5 . . ?
C5 C1 C2 112.8(2) . . ?
C5 C1 S1 108.13(17) . . ?
C2 C1 S1 105.64(16) . . ?
C5 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
S1 C1 H1 110.0 . . ?
N1 C2 C6 113.54(18) . . ?
N1 C2 C1 104.61(18) . . ?
C6 C2 C1 112.03(19) . . ?
N1 C2 H2A 108.8 . . ?
C6 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N1 C3 C4 122.8(2) . . ?
N1 C3 S1 112.15(18) . . ?
C4 C3 S1 125.06(18) . . ?
C3 C4 N2 122.0(2) . . ?
C3 C4 H4A 119.0 . . ?
N2 C4 H4A 119.0 . . ?
O1 C5 O2 124.8(2) . . ?
O1 C5 C1 123.0(2) . . ?
O2 C5 C1 112.1(2) . . ?
C11 C6 C7 119.0(2) . . ?
C11 C6 C2 123.0(2) . . ?
C7 C6 C2 118.0(2) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 119.8(2) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C17 C12 C13 120.4(2) . . ?
C17 C12 N1 118.7(2) . . ?
C13 C12 N1 120.9(2) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.0(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?

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
C3 S1 C1 C5 96.52(17) . . . . ?
C3 S1 C1 C2 -24.52(16) . . . . ?
C3 N1 C2 C6 93.6(2) . . . . ?
C12 N1 C2 C6 -85.2(2) . . . . ?
C3 N1 C2 C1 -28.8(2) . . . . ?
C12 N1 C2 C1 152.33(19) . . . . ?
C5 C1 C2 N1 -85.5(2) . . . . ?
S1 C1 C2 N1 32.4(2) . . . . ?
C5 C1 C2 C6 151.0(2) . . . . ?
S1 C1 C2 C6 -91.0(2) . . . . ?
C12 N1 C3 C4 10.7(3) . . . . ?
C2 N1 C3 C4 -168.1(2) . . . . ?
C12 N1 C3 S1 -170.71(16) . . . . ?
C2 N1 C3 S1 10.5(2) . . . . ?
C1 S1 C3 N1 9.19(17) . . . . ?
C1 S1 C3 C4 -172.3(2) . . . . ?
N1 C3 C4 N2 177.0(2) . . . . ?
S1 C3 C4 N2 -1.4(4) . . . . ?
O4 N2 C4 C3 -177.6(3) . . . . ?
O3 N2 C4 C3 0.3(4) . . . . ?
C2 C1 C5 O1 15.9(4) . . . . ?
S1 C1 C5 O1 -100.6(3) . . . . ?
C2 C1 C5 O2 -165.3(2) . . . . ?
S1 C1 C5 O2 78.2(2) . . . . ?
N1 C2 C6 C11 -20.7(3) . . . . ?
C1 C2 C6 C11 97.5(3) . . . . ?
N1 C2 C6 C7 160.2(2) . . . . ?
C1 C2 C6 C7 -81.5(3) . . . . ?
C11 C6 C7 C8 0.5(4) . . . . ?
C2 C6 C7 C8 179.6(2) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 -1.8(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C7 C6 C11 C10 -1.5(4) . . . . ?
C2 C6 C11 C10 179.4(2) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
C3 N1 C12 C17 77.4(3) . . . . ?
C2 N1 C12 C17 -103.9(3) . . . . ?
C3 N1 C12 C13 -102.3(3) . . . . ?
C2 N1 C12 C13 76.5(3) . . . . ?
C17 C12 C13 C14 -0.1(4) . . . . ?
N1 C12 C13 C14 179.6(2) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
N1 C12 C17 C16 -179.6(2) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

