# Electronic Supplementary Material (ESI) for ChemComm.
# 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_d20007
_database_code_depnum_ccdc_archive 'CCDC 1840927'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O4 S'
_chemical_formula_sum            'C18 H16 N2 O4 S'
_chemical_formula_weight         356.39

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   5.1019(5)
_cell_length_b                   33.051(3)
_cell_length_c                   9.4100(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.525(4)
_cell_angle_gamma                90.00
_cell_volume                     1585.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7856
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.074

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8509
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25241
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2800
_reflns_number_gt                2297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_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)+(0.0268P)²+1.9688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2800
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
C1 C 0.2566(8) 0.32261(11) 0.5855(4) 0.0516(10) Uani 1 1 d . . .
H1A H 0.0825 0.3279 0.5472 0.077 Uiso 1 1 calc R . .
H1B H 0.2483 0.3138 0.6824 0.077 Uiso 1 1 calc R . .
H1C H 0.3361 0.3019 0.5304 0.077 Uiso 1 1 calc R . .
C2 C 0.5439(6) 0.35671(9) 0.2985(3) 0.0273(7) Uani 1 1 d . . .
C3 C 0.8195(6) 0.31238(9) 0.2017(3) 0.0298(7) Uani 1 1 d . . .
C4 C 1.0183(6) 0.28318(9) 0.2179(4) 0.0364(8) Uani 1 1 d . . .
H4 H 1.0766 0.2753 0.3087 0.044 Uiso 1 1 calc R . .
C5 C 1.1271(7) 0.26623(10) 0.1025(4) 0.0405(9) Uani 1 1 d . . .
H5 H 1.2592 0.2470 0.1151 0.049 Uiso 1 1 calc R . .
C6 C 1.0408(7) 0.27764(10) -0.0347(4) 0.0414(9) Uani 1 1 d . . .
H6 H 1.1161 0.2659 -0.1130 0.050 Uiso 1 1 calc R . .
C7 C 0.8490(7) 0.30555(10) -0.0549(4) 0.0379(8) Uani 1 1 d . . .
H7 H 0.7937 0.3127 -0.1469 0.045 Uiso 1 1 calc R . .
C8 C 0.7315(6) 0.32397(9) 0.0618(3) 0.0299(7) Uani 1 1 d . . .
C9 C 0.5302(6) 0.35323(9) 0.0462(3) 0.0292(7) Uani 1 1 d . . .
H9 H 0.4643 0.3608 -0.0435 0.035 Uiso 1 1 calc R . .
C10 C 0.4350(6) 0.37001(9) 0.1656(3) 0.0266(7) Uani 1 1 d . . .
C11 C 0.2360(6) 0.39963(9) 0.1949(3) 0.0270(7) Uani 1 1 d . . .
C12 C 0.0639(6) 0.42198(9) 0.1068(3) 0.0314(7) Uani 1 1 d . . .
C13 C -0.1081(7) 0.43335(11) -0.1298(4) 0.0435(9) Uani 1 1 d . . .
H13A H -0.0840 0.4238 -0.2246 0.065 Uiso 1 1 calc R . .
H13B H -0.0873 0.4622 -0.1271 0.065 Uiso 1 1 calc R . .
H13C H -0.2811 0.4264 -0.1018 0.065 Uiso 1 1 calc R . .
C14 C -0.1085(6) 0.44872(10) 0.1658(3) 0.0336(8) Uani 1 1 d . . .
H14 H -0.2234 0.4638 0.1077 0.040 Uiso 1 1 calc R . .
C15 C -0.1092(6) 0.45288(10) 0.3129(3) 0.0347(8) Uani 1 1 d . . .
C16 C -0.4522(7) 0.50217(11) 0.2967(4) 0.0492(10) Uani 1 1 d . . .
H16A H -0.3580 0.5196 0.2351 0.074 Uiso 1 1 calc R . .
H16B H -0.5555 0.5183 0.3580 0.074 Uiso 1 1 calc R . .
H16C H -0.5653 0.4846 0.2405 0.074 Uiso 1 1 calc R . .
C17 C 0.0587(6) 0.43122(10) 0.4039(3) 0.0355(8) Uani 1 1 d . . .
H17 H 0.0574 0.4345 0.5020 0.043 Uiso 1 1 calc R . .
C18 C 0.2280(6) 0.40461(9) 0.3422(3) 0.0298(7) Uani 1 1 d . . .
N1 N 0.4219(5) 0.37881(8) 0.4077(3) 0.0333(6) Uani 1 1 d . . .
N2 N 0.7225(5) 0.32920(8) 0.3221(3) 0.0330(6) Uani 1 1 d . . .
O1 O 0.3198(5) 0.39768(8) 0.6543(2) 0.0521(7) Uani 1 1 d . . .
O2 O 0.7068(4) 0.35692(9) 0.6153(3) 0.0569(8) Uani 1 1 d . . .
O3 O 0.0817(4) 0.41508(7) -0.0347(2) 0.0420(6) Uani 1 1 d . . .
O4 O -0.2721(5) 0.47863(8) 0.3799(3) 0.0517(7) Uani 1 1 d . . .
S1 S 0.44251(16) 0.36641(3) 0.57930(8) 0.0339(2) Uani 1 1 d . . .


_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
C1 S1 1.733(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.300(4) . ?
C2 C10 1.415(4) . ?
C2 N1 1.426(4) . ?
C3 N2 1.373(4) . ?
C3 C4 1.403(4) . ?
C3 C8 1.424(4) . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.352(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(4) . ?
C9 C10 1.362(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.445(4) . ?
C11 C12 1.393(4) . ?
C11 C18 1.398(4) . ?
C12 O3 1.358(4) . ?
C12 C14 1.381(4) . ?
C13 O3 1.424(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9300 . ?
C15 O4 1.363(4) . ?
C15 C17 1.384(5) . ?
C16 O4 1.414(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 N1 1.425(4) . ?
N1 S1 1.665(3) . ?
O1 S1 1.413(2) . ?
O2 S1 1.411(2) . ?

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
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C10 127.8(3) . . ?
N2 C2 N1 124.1(3) . . ?
C10 C2 N1 108.1(3) . . ?
N2 C3 C4 118.3(3) . . ?
N2 C3 C8 122.9(3) . . ?
C4 C3 C8 118.8(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 123.1(3) . . ?
C7 C8 C3 118.4(3) . . ?
C9 C8 C3 118.5(3) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C2 117.5(3) . . ?
C9 C10 C11 135.4(3) . . ?
C2 C10 C11 107.1(3) . . ?
C12 C11 C18 118.9(3) . . ?
C12 C11 C10 132.5(3) . . ?
C18 C11 C10 108.7(3) . . ?
O3 C12 C14 125.0(3) . . ?
O3 C12 C11 115.3(3) . . ?
C14 C12 C11 119.7(3) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 119.6(3) . . ?
C12 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
O4 C15 C17 114.2(3) . . ?
O4 C15 C14 123.4(3) . . ?
C17 C15 C14 122.4(3) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 116.9(3) . . ?
C18 C17 H17 121.6 . . ?
C15 C17 H17 121.6 . . ?
C17 C18 C11 122.6(3) . . ?
C17 C18 N1 129.5(3) . . ?
C11 C18 N1 107.9(3) . . ?
C18 N1 C2 108.2(2) . . ?
C18 N1 S1 125.4(2) . . ?
C2 N1 S1 124.2(2) . . ?
C2 N2 C3 114.7(3) . . ?
C12 O3 C13 118.2(2) . . ?
C15 O4 C16 118.8(3) . . ?
O2 S1 O1 118.84(16) . . ?
O2 S1 N1 107.82(14) . . ?
O1 S1 N1 107.11(14) . . ?
O2 S1 C1 108.96(19) . . ?
O1 S1 C1 109.80(18) . . ?
N1 S1 C1 103.14(17) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.053
