# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_zk-4-125
_database_code_depnum_ccdc_archive 'CCDC 1884631'
loop_
_audit_author_name
_audit_author_address
'Bin Xu'
;Shanghai University
China
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'5-methyl-3-(4-nitrophenyl)-5,6a-dihydroisothiazolo[5,4-d]isoxazol-6(3aH)-one 4,4-dioxide'
_chemical_name_common            ?
_chemical_melting_point          533-534
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O6 S'
_chemical_formula_weight         311.27

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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'
'-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                   6.495(3)
_cell_length_b                   17.713(8)
_cell_length_c                   21.586(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2483(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2890
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0.0
_diffrn_standards_interval_count 0.0
_diffrn_standards_interval_time  0.0
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            14604
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.78
_reflns_number_total             2926
_reflns_number_gt                2306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0585P)²+0.8699P] 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         2926
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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 1.0792(3) -0.08135(11) 0.13359(9) 0.0411(4) Uani 1 1 d . . .
C2 C 1.0922(3) -0.14840(11) 0.10098(9) 0.0425(4) Uani 1 1 d . . .
H2 H 0.9899 -0.1625 0.0731 0.051 Uiso 1 1 calc R . .
C3 C 1.2622(3) -0.19371(11) 0.11115(9) 0.0391(4) Uani 1 1 d . . .
H3 H 1.2734 -0.2394 0.0902 0.047 Uiso 1 1 calc R . .
C4 C 1.4165(3) -0.17234(10) 0.15202(8) 0.0350(4) Uani 1 1 d . . .
C5 C 1.4001(3) -0.10258(11) 0.18229(10) 0.0443(5) Uani 1 1 d . . .
H5 H 1.5047 -0.0867 0.2087 0.053 Uiso 1 1 calc R . .
C6 C 1.2301(3) -0.05732(11) 0.17320(10) 0.0475(5) Uani 1 1 d . . .
H6 H 1.2182 -0.0113 0.1936 0.057 Uiso 1 1 calc R . .
C7 C 1.5887(3) -0.22254(10) 0.16725(8) 0.0342(4) Uani 1 1 d . . .
C8 C 1.6006(3) -0.30555(10) 0.15338(8) 0.0324(4) Uani 1 1 d . . .
C9 C 1.7892(3) -0.32852(11) 0.19042(9) 0.0383(4) Uani 1 1 d . . .
C10 C 1.9525(3) -0.36280(10) 0.14920(9) 0.0370(4) Uani 1 1 d . . .
C11 C 2.0137(3) -0.39671(12) 0.03865(10) 0.0479(5) Uani 1 1 d . . .
H11A H 1.9427 -0.3900 0.0000 0.072 Uiso 1 1 calc R . .
H11B H 2.0311 -0.4497 0.0466 0.072 Uiso 1 1 calc R . .
H11C H 2.1463 -0.3729 0.0365 0.072 Uiso 1 1 calc R . .
N2 N 1.7408(3) -0.19874(10) 0.19934(8) 0.0430(4) Uani 1 1 d . . .
N1 N 0.8913(3) -0.03565(10) 0.12716(9) 0.0529(5) Uani 1 1 d . . .
N3 N 1.8934(2) -0.36259(9) 0.08874(7) 0.0370(4) Uani 1 1 d . . .
O5 O 1.6913(2) -0.25809(8) 0.03886(6) 0.0484(4) Uani 1 1 d . . .
O6 O 1.5324(2) -0.38257(8) 0.04886(7) 0.0496(4) Uani 1 1 d . . .
O3 O 1.8726(2) -0.25835(9) 0.21437(7) 0.0493(4) Uani 1 1 d . . .
O1 O 0.8630(3) 0.01440(10) 0.16603(9) 0.0709(5) Uani 1 1 d . . .
O2 O 0.7723(3) -0.05012(11) 0.08542(9) 0.0704(5) Uani 1 1 d . . .
O4 O 2.1180(2) -0.38446(9) 0.16774(7) 0.0522(4) Uani 1 1 d . . .
S1 S 1.66315(7) -0.32581(3) 0.073403(19) 0.03396(14) Uani 1 1 d . . .
H8 H 1.481(3) -0.3330(11) 0.1624(9) 0.037(5) Uiso 1 1 d . . .
H9 H 1.755(3) -0.3607(11) 0.2234(10) 0.037(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0420(11) 0.0374(10) 0.0439(10) 0.0077(8) 0.0097(8) 0.0025(8)
C2 0.0400(10) 0.0480(11) 0.0394(10) -0.0006(8) 0.0022(8) 0.0006(9)
C3 0.0402(10) 0.0403(10) 0.0366(9) -0.0062(8) 0.0027(8) 0.0008(8)
C4 0.0355(9) 0.0360(9) 0.0335(9) -0.0003(7) 0.0068(7) -0.0032(7)
C5 0.0460(11) 0.0397(10) 0.0471(11) -0.0083(9) -0.0006(9) -0.0049(8)
C6 0.0547(13) 0.0332(10) 0.0547(12) -0.0054(9) 0.0081(10) -0.0024(9)
C7 0.0337(9) 0.0400(10) 0.0288(8) -0.0041(7) 0.0038(7) -0.0062(7)
C8 0.0288(9) 0.0389(9) 0.0293(8) -0.0002(7) 0.0013(7) -0.0036(7)
C9 0.0377(10) 0.0457(11) 0.0315(9) 0.0032(8) -0.0038(8) -0.0051(8)
C10 0.0336(9) 0.0371(10) 0.0403(10) 0.0022(8) -0.0061(7) -0.0021(7)
C11 0.0407(11) 0.0540(12) 0.0489(12) -0.0045(9) 0.0086(9) 0.0063(9)
N2 0.0380(9) 0.0485(9) 0.0424(9) -0.0092(7) -0.0012(7) -0.0020(7)
N1 0.0547(11) 0.0432(10) 0.0607(12) 0.0111(9) 0.0122(10) 0.0091(8)
N3 0.0311(8) 0.0434(9) 0.0365(8) -0.0008(7) -0.0001(6) 0.0026(7)
O5 0.0589(9) 0.0500(8) 0.0365(7) 0.0073(6) 0.0046(6) 0.0100(7)
O6 0.0397(8) 0.0612(9) 0.0481(8) -0.0187(7) -0.0081(6) -0.0030(7)
O3 0.0418(8) 0.0563(9) 0.0496(8) -0.0142(7) -0.0143(6) 0.0021(7)
O1 0.0810(13) 0.0544(10) 0.0773(12) -0.0028(9) 0.0120(10) 0.0263(9)
O2 0.0580(11) 0.0728(12) 0.0805(12) 0.0041(10) -0.0127(9) 0.0165(9)
O4 0.0405(8) 0.0570(9) 0.0592(9) 0.0007(7) -0.0148(7) 0.0083(7)
S1 0.0311(2) 0.0411(3) 0.0297(2) -0.00272(17) -0.00233(17) 0.00271(18)

_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 C6 1.368(3) . ?
C1 C2 1.383(3) . ?
C1 N1 1.471(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.402(3) . ?
C4 C7 1.466(3) . ?
C5 C6 1.378(3) . ?
C7 N2 1.278(2) . ?
C7 C8 1.502(3) . ?
C8 C9 1.519(3) . ?
C8 S1 1.8095(19) . ?
C9 O3 1.451(2) . ?
C9 C10 1.512(3) . ?
C10 O4 1.209(2) . ?
C10 N3 1.361(2) . ?
C11 N3 1.465(2) . ?
N2 O3 1.398(2) . ?
N1 O2 1.214(3) . ?
N1 O1 1.235(2) . ?
N3 S1 1.6644(17) . ?
O5 S1 1.4241(15) . ?
O6 S1 1.4188(15) . ?

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
C6 C1 C2 122.79(19) . . ?
C6 C1 N1 118.82(19) . . ?
C2 C1 N1 118.34(19) . . ?
C3 C2 C1 117.79(19) . . ?
C2 C3 C4 121.28(18) . . ?
C3 C4 C5 118.82(18) . . ?
C3 C4 C7 121.86(16) . . ?
C5 C4 C7 119.20(17) . . ?
C6 C5 C4 120.47(19) . . ?
C1 C6 C5 118.79(19) . . ?
N2 C7 C4 120.73(17) . . ?
N2 C7 C8 113.04(17) . . ?
C4 C7 C8 126.01(16) . . ?
C7 C8 C9 101.45(15) . . ?
C7 C8 S1 113.31(12) . . ?
C9 C8 S1 105.54(13) . . ?
O3 C9 C10 106.98(16) . . ?
O3 C9 C8 105.03(16) . . ?
C10 C9 C8 111.33(15) . . ?
O4 C10 N3 124.69(19) . . ?
O4 C10 C9 123.79(18) . . ?
N3 C10 C9 111.45(16) . . ?
C7 N2 O3 110.49(16) . . ?
O2 N1 O1 124.1(2) . . ?
O2 N1 C1 118.81(19) . . ?
O1 N1 C1 117.0(2) . . ?
C10 N3 C11 123.81(17) . . ?
C10 N3 S1 116.45(13) . . ?
C11 N3 S1 119.62(13) . . ?
N2 O3 C9 109.62(14) . . ?
O6 S1 O5 118.57(10) . . ?
O6 S1 N3 109.56(9) . . ?
O5 S1 N3 108.57(9) . . ?
O6 S1 C8 111.24(9) . . ?
O5 S1 C8 111.18(9) . . ?
N3 S1 C8 95.15(8) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.78
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.048
