# Electronic Supplementary Material (ESI) for Toxicology Research.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_rc84
_database_code_depnum_ccdc_archive 'CCDC 1054657'
_audit_update_record             
;
2015-03-18 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 O3 S, C3 H5 N2'
_chemical_formula_sum            'C10 H12 N2 O3 S'

_chemical_formula_weight         240.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.36375(15)
_cell_length_b                   15.7571(3)
_cell_length_c                   15.7989(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9318(17)
_cell_angle_gamma                90.00
_cell_volume                     2288.76(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4721
_cell_measurement_theta_min      4.0000
_cell_measurement_theta_max      71.7410

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      1.395
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1008.0
_exptl_absorpt_coefficient_mu    2.494
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.57306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9486
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.8043
_diffrn_reflns_theta_max         71.78
_reflns_number_total             4398
_reflns_number_gt                3883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0992P)²+0.8363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4398
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.012
_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 0.87081(5) 0.39488(4) 0.19466(4) 0.04283(19) Uani 1 1 d . . .
S2 S 0.57105(6) 0.75091(4) 0.63634(3) 0.0476(2) Uani 1 1 d . . .
O1 O 0.99881(17) 0.34022(11) 0.20677(12) 0.0521(4) Uani 1 1 d . . .
O3 O 0.74759(16) 0.34996(12) 0.21793(13) 0.0561(5) Uani 1 1 d . . .
O6 O 0.45913(18) 0.72476(14) 0.68396(11) 0.0581(5) Uani 1 1 d . . .
O4 O 0.71510(17) 0.72395(14) 0.68165(11) 0.0591(5) Uani 1 1 d . . .
O2 O 0.8372(2) 0.43334(14) 0.11040(12) 0.0623(5) Uani 1 1 d . . .
N2 N 0.3092(2) 0.36511(15) 0.17212(13) 0.0546(5) Uani 1 1 d . . .
H18 H 0.2771 0.3381 0.2120 0.065 Uiso 1 1 calc R . .
C1 C 0.9121(2) 0.47737(15) 0.27057(15) 0.0466(5) Uani 1 1 d . . .
N1 N 0.4472(2) 0.37307(17) 0.16629(14) 0.0609(6) Uani 1 1 d . . .
H19 H 0.5196 0.3518 0.2016 0.073 Uiso 1 1 calc R . .
O5 O 0.5638(2) 0.83951(14) 0.61387(13) 0.0683(5) Uani 1 1 d . . .
C8 C 0.5370(2) 0.69351(17) 0.53868(14) 0.0480(5) Uani 1 1 d . . .
C17 C 0.2292(3) 0.4050(2) 0.10728(17) 0.0589(7) Uani 1 1 d . . .
H17 H 0.1282 0.4085 0.0967 0.071 Uiso 1 1 calc R . .
C16 C 0.3178(3) 0.4405(2) 0.05799(17) 0.0600(7) Uani 1 1 d . . .
H16 H 0.2904 0.4725 0.0081 0.072 Uiso 1 1 calc R . .
C11 C 0.4727(4) 0.6006(2) 0.3859(2) 0.0739(9) Uani 1 1 d . . .
C15 C 0.4564(3) 0.4188(2) 0.0979(2) 0.0683(8) Uani 1 1 d . . .
H15 H 0.5418 0.4339 0.0797 0.082 Uiso 1 1 calc R . .
C6 C 1.0316(4) 0.4720(2) 0.3359(2) 0.0790(10) Uani 1 1 d . . .
H4 H 1.0945 0.4259 0.3390 0.095 Uiso 1 1 calc R . .
C5 C 1.0575(5) 0.5357(3) 0.3969(3) 0.0997(13) Uani 1 1 d . . .
H3 H 1.1368 0.5310 0.4421 0.120 Uiso 1 1 calc R . .
C7 C 0.9996(8) 0.6753(3) 0.4598(3) 0.137(2) Uani 1 1 d . . .
H6A H 1.0350 0.6508 0.5154 0.205 Uiso 1 1 calc R . .
H5B H 0.9115 0.7060 0.4610 0.205 Uiso 1 1 calc R . .
H7C H 1.0715 0.7134 0.4454 0.205 Uiso 1 1 calc R . .
C12 C 0.3939(5) 0.6698(2) 0.3987(2) 0.0905(12) Uani 1 1 d . . .
H10 H 0.3165 0.6861 0.3557 0.109 Uiso 1 1 calc R . .
C13 C 0.4250(4) 0.7168(2) 0.4735(2) 0.0818(10) Uani 1 1 d . . .
H11 H 0.3697 0.7646 0.4798 0.098 Uiso 1 1 calc R . .
C14 C 0.4378(6) 0.5486(3) 0.3036(3) 0.1089(15) Uani 1 1 d . . .
H14A H 0.3343 0.5439 0.2858 0.163 Uiso 1 1 calc R . .
H12B H 0.4794 0.4930 0.3138 0.163 Uiso 1 1 calc R . .
H13C H 0.4778 0.5761 0.2591 0.163 Uiso 1 1 calc R . .
C2 C 0.8219(4) 0.5472(2) 0.2661(2) 0.0724(8) Uani 1 1 d . . .
H1A H 0.7414 0.5519 0.2217 0.087 Uiso 1 1 calc R . .
C9 C 0.6150(4) 0.6227(3) 0.5273(2) 0.0976(14) Uani 1 1 d . . .
H8 H 0.6904 0.6052 0.5709 0.117 Uiso 1 1 calc R . .
C10 C 0.5830(5) 0.5771(4) 0.4520(3) 0.1130(17) Uani 1 1 d . . .
H9 H 0.6376 0.5291 0.4457 0.136 Uiso 1 1 calc R . .
C4 C 0.9696(5) 0.6055(2) 0.3926(3) 0.0844(10) Uani 1 1 d . . .
C3 C 0.8516(5) 0.6097(2) 0.3278(3) 0.0904(12) Uani 1 1 d . . .
H2 H 0.7893 0.6560 0.3250 0.109 Uiso 1 1 calc R . .
N4 N 0.1612(3) 0.71715(15) 0.16681(15) 0.0652(7) Uani 1 1 d . . .
H23 H 0.2257 0.7508 0.1947 0.078 Uiso 1 1 calc R . .
C20 C 0.0222(3) 0.71833(15) 0.16976(16) 0.0511(6) Uani 1 1 d . . .
H22 H -0.0223 0.7557 0.2023 0.061 Uiso 1 1 calc R . .
C19 C -0.0437(3) 0.65885(19) 0.1199(2) 0.0655(7) Uani 1 1 d . . .
H21 H -0.1426 0.6468 0.1109 0.079 Uiso 1 1 calc R . .
N3 N 0.1866(3) 0.6559(2) 0.1141(2) 0.0790(8) Uani 1 1 d . . .
H24A H 0.2694 0.6429 0.1016 0.095 Uiso 1 1 calc R . .
C18 C 0.0565(3) 0.61730(18) 0.0832(2) 0.0624(7) Uani 1 1 d . . .
H20 H 0.0399 0.5719 0.0449 0.075 Uiso 1 1 calc R . .


_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 1.4421(18) . ?
S1 O3 1.4588(16) . ?
S1 O1 1.4587(16) . ?
S1 C1 1.761(3) . ?
S2 O5 1.439(2) . ?
S2 O6 1.4605(17) . ?
S2 O4 1.4650(17) . ?
S2 C8 1.765(3) . ?
N2 C17 1.310(3) . ?
N2 N1 1.318(3) . ?
C1 C6 1.374(4) . ?
C1 C2 1.381(4) . ?
N1 C15 1.316(4) . ?
C8 C9 1.364(5) . ?
C8 C13 1.373(4) . ?
C17 C16 1.361(4) . ?
C16 C15 1.374(4) . ?
C11 C12 1.354(5) . ?
C11 C10 1.373(5) . ?
C11 C14 1.519(5) . ?
C6 C5 1.381(5) . ?
C5 C4 1.367(6) . ?
C7 C4 1.518(5) . ?
C12 C13 1.378(5) . ?
C2 C3 1.376(5) . ?
C9 C10 1.373(6) . ?
C4 C3 1.358(6) . ?
N4 C20 1.311(4) . ?
N4 N3 1.326(4) . ?
C20 C19 1.302(4) . ?
C19 C18 1.361(4) . ?
N3 C18 1.366(4) . ?

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 O3 113.08(11) . . ?
O2 S1 O1 113.53(11) . . ?
O3 S1 O1 110.48(10) . . ?
O2 S1 C1 107.44(12) . . ?
O3 S1 C1 105.57(11) . . ?
O1 S1 C1 106.12(11) . . ?
O5 S2 O6 113.33(13) . . ?
O5 S2 O4 113.44(13) . . ?
O6 S2 O4 110.52(10) . . ?
O5 S2 C8 106.82(12) . . ?
O6 S2 C8 106.10(11) . . ?
O4 S2 C8 106.01(12) . . ?
C17 N2 N1 108.8(2) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 S1 120.6(2) . . ?
C2 C1 S1 120.0(2) . . ?
C15 N1 N2 109.1(2) . . ?
C9 C8 C13 118.1(3) . . ?
C9 C8 S2 121.4(2) . . ?
C13 C8 S2 120.3(2) . . ?
N2 C17 C16 108.9(2) . . ?
C17 C16 C15 105.1(2) . . ?
C12 C11 C10 117.1(3) . . ?
C12 C11 C14 121.8(4) . . ?
C10 C11 C14 121.0(4) . . ?
N1 C15 C16 108.0(2) . . ?
C1 C6 C5 119.4(3) . . ?
C4 C5 C6 121.7(4) . . ?
C11 C12 C13 121.9(3) . . ?
C8 C13 C12 120.5(3) . . ?
C3 C2 C1 119.6(3) . . ?
C8 C9 C10 120.5(3) . . ?
C9 C10 C11 121.8(4) . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 C7 120.5(4) . . ?
C5 C4 C7 121.2(4) . . ?
C4 C3 C2 121.7(3) . . ?
C20 N4 N3 109.3(2) . . ?
C19 C20 N4 109.1(2) . . ?
C20 C19 C18 108.6(3) . . ?
N4 N3 C18 107.1(3) . . ?
C19 C18 N3 105.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        71.78
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.149
