##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H6 N2 O2 S2'
_chemical_formula_sum     'C11 H6 N2 O2 S2'
_chemical_formula_iupac     'C11 H6 N2 O2 S2'
_chemical_formula_weight     262.30
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.2739(7)
_cell_length_b     11.2713(11)
_cell_length_c     14.6909(15)
_cell_angle_alpha     87.5620(10)
_cell_angle_beta     78.3410(10)
_cell_angle_gamma     71.6240(10)
_cell_volume     1119.16(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5699
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     28.57
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.557
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.464
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_shelx_estimated_absorpt_T_min     0.804
_shelx_estimated_absorpt_T_max     0.936
_exptl_absorpt_correction_T_min     0.8038
_exptl_absorpt_correction_T_max     0.9358
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7476
_diffrn_reflns_av_R_equivalents     0.0154
_diffrn_reflns_theta_min     1.904
_diffrn_reflns_theta_max     25.000
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.977
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details     ?
_reflns_number_total     3862
_reflns_number_gt     3485
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0349
_refine_ls_R_factor_gt     0.0314
_refine_ls_wR_factor_gt     0.1015
_refine_ls_wR_factor_ref     0.1060
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     3862
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0697P)²+0.2729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.334
_refine_diff_density_min     -0.231
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.031(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics     ?
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.85294(8) 0.03895(4) 0.15683(4) 0.05223(17) Uani d 1 . .
    O O1 0.8238(2) 0.18576(13) 0.30252(9) 0.0593(4) Uani d 1 . .
    N N1 0.8263(3) 0.12000(15) 0.05875(12) 0.0510(4) Uani d 1 . .
    C C1 0.8229(3) 0.17293(17) 0.22295(13) 0.0446(4) Uani d 1 . .
    S S2 0.77918(10) 0.29901(5) -0.10629(4) 0.05823(18) Uani d 1 . .
    O O2 0.7971(2) 0.27252(11) 0.16249(8) 0.0443(3) Uani d 1 . .
    N N2 0.7537(3) 0.44255(17) -0.14107(11) 0.0541(4) Uani d 1 . .
    C C2 0.8016(3) 0.23440(17) 0.07498(12) 0.0415(4) Uani d 1 . .
    S S3 0.59888(8) 0.83750(5) 0.55508(4) 0.05152(17) Uani d 1 . .
    O O3 0.6679(3) 0.59670(16) 0.59752(14) 0.0797(5) Uani d 1 . .
    N N3 0.4193(2) 0.89051(14) 0.49359(11) 0.0454(4) Uani d 1 . .
    C C3 0.7806(3) 0.33109(18) 0.00604(12) 0.0415(4) Uani d 1 . .
    S S4 0.09624(8) 0.94818(4) 0.37616(4) 0.05119(17) Uani d 1 . .
    O O4 0.4345(2) 0.68529(12) 0.51338(9) 0.0472(3) Uani d 1 . .
    N N4 -0.0487(3) 0.89146(15) 0.33086(11) 0.0479(4) Uani d 1 . .
    C C4 0.7628(3) 0.45417(17) 0.01441(12) 0.0419(4) Uani d 1 . .
    H H4B 0.7607 0.4931 0.0693 0.050 Uiso calc 1 . .
    C C5 0.7479(3) 0.51552(18) -0.07130(12) 0.0410(4) Uani d 1 . .
    C C6 0.7266(3) 0.64887(18) -0.08776(13) 0.0425(4) Uani d 1 . .
    C C7 0.7228(3) 0.72818(19) -0.01704(14) 0.0503(5) Uani d 1 . .
    H H7A 0.7348 0.6969 0.0418 0.060 Uiso calc 1 . .
    C C8 0.7015(3) 0.8528(2) -0.03326(18) 0.0604(6) Uani d 1 . .
    H H8A 0.6980 0.9050 0.0149 0.073 Uiso calc 1 . .
    C C9 0.6854(3) 0.9007(2) -0.12035(19) 0.0652(6) Uani d 1 . .
    H H9A 0.6719 0.9847 -0.1312 0.078 Uiso calc 1 . .
    C C10 0.6895(4) 0.8231(2) -0.19106(17) 0.0658(6) Uani d 1 . .
    H H10A 0.6784 0.8551 -0.2498 0.079 Uiso calc 1 . .
    C C11 0.7101(3) 0.6982(2) -0.17573(15) 0.0553(5) Uani d 1 . .
    H H11A 0.7129 0.6467 -0.2242 0.066 Uiso calc 1 . .
    C C12 0.5796(3) 0.68671(19) 0.56116(15) 0.0526(5) Uani d 1 . .
    C C13 0.3557(3) 0.80060(16) 0.47969(12) 0.0396(4) Uani d 1 . .
    C C14 0.2024(3) 0.81178(16) 0.42756(12) 0.0399(4) Uani d 1 . .
    C C15 0.1224(3) 0.72317(17) 0.40912(12) 0.0411(4) Uani d 1 . .
    H H15A 0.1576 0.6415 0.4299 0.049 Uiso calc 1 . .
    C C16 -0.0219(3) 0.77277(16) 0.35387(12) 0.0400(4) Uani d 1 . .
    C C17 -0.1434(3) 0.70474(18) 0.32326(12) 0.0430(4) Uani d 1 . .
    C C18 -0.2967(3) 0.7675(2) 0.27896(14) 0.0523(5) Uani d 1 . .
    H H18A -0.3229 0.8525 0.2681 0.063 Uiso calc 1 . .
    C C19 -0.4109(3) 0.7038(2) 0.25083(15) 0.0595(6) Uani d 1 . .
    H H19A -0.5127 0.7462 0.2207 0.071 Uiso calc 1 . .
    C C20 -0.3750(3) 0.5778(2) 0.26715(16) 0.0622(6) Uani d 1 . .
    H H20A -0.4528 0.5355 0.2485 0.075 Uiso calc 1 . .
    C C21 -0.2239(4) 0.5153(2) 0.31101(18) 0.0665(6) Uani d 1 . .
    H H21A -0.1988 0.4303 0.3219 0.080 Uiso calc 1 . .
    C C22 -0.1083(3) 0.5782(2) 0.33915(16) 0.0551(5) Uani d 1 . .
    H H22A -0.0063 0.5351 0.3690 0.066 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.6845(17) ?
    S1 C1 . 1.7616(19) ?
    O1 C1 . 1.185(2) ?
    N1 C2 . 1.271(2) ?
    C1 O2 . 1.391(2) ?
    S2 N2 . 1.6406(18) ?
    S2 C3 . 1.7071(18) ?
    O2 C2 . 1.364(2) ?
    N2 C5 . 1.327(2) ?
    C2 C3 . 1.449(3) ?
    S3 N3 . 1.6790(16) ?
    S3 C12 . 1.746(2) ?
    O3 C12 . 1.187(3) ?
    N3 C13 . 1.278(2) ?
    C3 C4 . 1.361(3) ?
    S4 N4 . 1.6457(17) ?
    S4 C14 . 1.7084(18) ?
    O4 C13 . 1.361(2) ?
    O4 C12 . 1.385(2) ?
    N4 C16 . 1.329(2) ?
    C4 C5 . 1.417(3) ?
    C4 H4B . 0.9300 ?
    C5 C6 . 1.476(3) ?
    C6 C7 . 1.390(3) ?
    C6 C11 . 1.398(3) ?
    C7 C8 . 1.380(3) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.380(3) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.376(4) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.382(3) ?
    C10 H10A . 0.9300 ?
    C11 H11A . 0.9300 ?
    C13 C14 . 1.447(3) ?
    C14 C15 . 1.365(3) ?
    C15 C16 . 1.417(3) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.479(3) ?
    C17 C22 . 1.386(3) ?
    C17 C18 . 1.387(3) ?
    C18 C19 . 1.384(3) ?
    C18 H18A . 0.9300 ?
    C19 C20 . 1.380(4) ?
    C19 H19A . 0.9300 ?
    C20 C21 . 1.371(4) ?
    C20 H20A . 0.9300 ?
    C21 C22 . 1.386(3) ?
    C21 H21A . 0.9300 ?
    C22 H22A . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C1 . . 93.13(8) ?
    C2 N1 S1 . . 109.43(14) ?
    O1 C1 O2 . . 122.21(17) ?
    O1 C1 S1 . . 131.23(16) ?
    O2 C1 S1 . . 106.56(13) ?
    N2 S2 C3 . . 94.78(9) ?
    C2 O2 C1 . . 111.28(14) ?
    C5 N2 S2 . . 110.54(13) ?
    N1 C2 O2 . . 119.58(17) ?
    N1 C2 C3 . . 124.86(17) ?
    O2 C2 C3 . . 115.55(16) ?
    N3 S3 C12 . . 93.31(9) ?
    C13 N3 S3 . . 108.63(13) ?
    C4 C3 C2 . . 129.89(17) ?
    C4 C3 S2 . . 108.82(14) ?
    C2 C3 S2 . . 121.28(14) ?
    N4 S4 C14 . . 94.50(9) ?
    C13 O4 C12 . . 110.20(15) ?
    C16 N4 S4 . . 110.35(13) ?
    C3 C4 C5 . . 111.36(16) ?
    C3 C4 H4B . . 124.3 ?
    C5 C4 H4B . . 124.3 ?
    N2 C5 C4 . . 114.50(17) ?
    N2 C5 C6 . . 119.40(16) ?
    C4 C5 C6 . . 126.10(16) ?
    C7 C6 C11 . . 118.40(19) ?
    C7 C6 C5 . . 121.30(17) ?
    C11 C6 C5 . . 120.29(18) ?
    C8 C7 C6 . . 120.7(2) ?
    C8 C7 H7A . . 119.7 ?
    C6 C7 H7A . . 119.7 ?
    C7 C8 C9 . . 120.5(2) ?
    C7 C8 H8A . . 119.7 ?
    C9 C8 H8A . . 119.7 ?
    C10 C9 C8 . . 119.4(2) ?
    C10 C9 H9A . . 120.3 ?
    C8 C9 H9A . . 120.3 ?
    C9 C10 C11 . . 120.7(2) ?
    C9 C10 H10A . . 119.6 ?
    C11 C10 H10A . . 119.6 ?
    C10 C11 C6 . . 120.3(2) ?
    C10 C11 H11A . . 119.9 ?
    C6 C11 H11A . . 119.9 ?
    O3 C12 O4 . . 122.3(2) ?
    O3 C12 S3 . . 130.15(18) ?
    O4 C12 S3 . . 107.58(13) ?
    N3 C13 O4 . . 120.27(17) ?
    N3 C13 C14 . . 123.90(17) ?
    O4 C13 C14 . . 115.82(16) ?
    C15 C14 C13 . . 128.92(17) ?
    C15 C14 S4 . . 109.41(14) ?
    C13 C14 S4 . . 121.66(14) ?
    C14 C15 C16 . . 110.62(16) ?
    C14 C15 H15A . . 124.7 ?
    C16 C15 H15A . . 124.7 ?
    N4 C16 C15 . . 115.12(16) ?
    N4 C16 C17 . . 119.36(16) ?
    C15 C16 C17 . . 125.51(16) ?
    C22 C17 C18 . . 118.80(18) ?
    C22 C17 C16 . . 120.93(18) ?
    C18 C17 C16 . . 120.26(17) ?
    C19 C18 C17 . . 120.2(2) ?
    C19 C18 H18A . . 119.9 ?
    C17 C18 H18A . . 119.9 ?
    C20 C19 C18 . . 120.6(2) ?
    C20 C19 H19A . . 119.7 ?
    C18 C19 H19A . . 119.7 ?
    C21 C20 C19 . . 119.5(2) ?
    C21 C20 H20A . . 120.2 ?
    C19 C20 H20A . . 120.2 ?
    C20 C21 C22 . . 120.3(2) ?
    C20 C21 H21A . . 119.8 ?
    C22 C21 H21A . . 119.8 ?
    C17 C22 C21 . . 120.6(2) ?
    C17 C22 H22A . . 119.7 ?
    C21 C22 H22A . . 119.7 ?
data_II
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H6 N2 O2 S2'
_chemical_formula_sum     'C11 H6 N2 O2 S2'
_chemical_formula_iupac     'C11 H6 N2 O2 S2'
_chemical_formula_weight     262.30
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
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     9.7202(6)
_cell_length_b     9.9723(6)
_cell_length_c     11.2165(7)
_cell_angle_alpha     90
_cell_angle_beta     90.3990(10)
_cell_angle_gamma     90
_cell_volume     1087.22(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6714
_cell_measurement_theta_min     2.73
_cell_measurement_theta_max     28.28
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.483
_exptl_crystal_size_mid     0.425
_exptl_crystal_size_min     0.372
_exptl_crystal_density_diffrn     1.602
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.478
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.719
_exptl_absorpt_correction_T_max     0.837
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8041
_diffrn_reflns_av_R_equivalents     0.0168
_diffrn_reflns_theta_min     2.926
_diffrn_reflns_theta_max     26.995
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details     ?
_reflns_number_total     2362
_reflns_number_gt     2228
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0309
_refine_ls_R_factor_gt     0.0297
_refine_ls_wR_factor_gt     0.0814
_refine_ls_wR_factor_ref     0.0831
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.016
_refine_ls_number_reflns     2362
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0465P)²+0.4061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.367
_refine_diff_density_min     -0.276
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.018(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics     ?
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S2 0.45224(4) 0.17168(4) 0.50567(3) 0.04262(13) Uani d 1 . .
    S S1 0.88687(4) 0.63218(4) 0.59213(4) 0.04650(14) Uani d 1 . .
    O O1 0.65815(9) 0.53305(10) 0.65111(8) 0.0330(2) Uani d 1 . .
    C C1 0.74809(14) 0.63165(15) 0.69017(12) 0.0365(3) Uani d 1 . .
    C C3 0.62185(13) 0.35992(13) 0.50912(11) 0.0288(3) Uani d 1 . .
    O O2 0.72696(12) 0.69783(14) 0.77664(11) 0.0542(3) Uani d 1 . .
    C C2 0.70630(13) 0.47087(13) 0.55025(10) 0.0288(3) Uani d 1 . .
    N N2 0.55493(14) 0.18187(13) 0.38899(11) 0.0427(3) Uani d 1 . .
    N N1 0.82008(12) 0.51010(13) 0.50596(10) 0.0395(3) Uani d 1 . .
    C C4 0.51836(13) 0.30589(14) 0.57667(12) 0.0330(3) Uani d 1 . .
    H H4 0.4894 0.3384 0.6501 0.040 Uiso calc 1 . .
    C C5 0.63936(13) 0.28477(14) 0.40146(11) 0.0325(3) Uani d 1 . .
    C C6 0.74116(14) 0.31005(14) 0.30578(11) 0.0337(3) Uani d 1 . .
    C C11 0.83741(15) 0.21201(15) 0.27851(13) 0.0386(3) Uani d 1 . .
    H H11A 0.8384 0.1317 0.3206 0.046 Uiso calc 1 . .
    C C7 0.73957(18) 0.42883(17) 0.24153(14) 0.0472(4) Uani d 1 . .
    H H7A 0.6757 0.4951 0.2595 0.057 Uiso calc 1 . .
    C C10 0.93225(15) 0.23383(18) 0.18830(14) 0.0465(4) Uani d 1 . .
    H H10A 0.9976 0.1687 0.1710 0.056 Uiso calc 1 . .
    C C9 0.92952(19) 0.3518(2) 0.12467(15) 0.0530(4) Uani d 1 . .
    H H9A 0.9927 0.3662 0.0641 0.064 Uiso calc 1 . .
    C C8 0.8330(2) 0.4488(2) 0.15076(15) 0.0560(4) Uani d 1 . .
    H H8A 0.8307 0.5280 0.1070 0.067 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S2 N2 . 1.6546(13) ?
    S2 C4 . 1.6827(14) ?
    S1 N1 . 1.6820(12) ?
    S1 C1 . 1.7463(14) ?
    O1 C2 . 1.3750(14) ?
    O1 C1 . 1.3849(17) ?
    C1 O2 . 1.1921(17) ?
    C3 C4 . 1.3737(18) ?
    C3 C5 . 1.4324(17) ?
    C3 C2 . 1.4511(18) ?
    C2 N1 . 1.2770(17) ?
    N2 C5 . 1.3208(18) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.4864(18) ?
    C6 C7 . 1.386(2) ?
    C6 C11 . 1.389(2) ?
    C11 C10 . 1.391(2) ?
    C11 H11A . 0.9300 ?
    C7 C8 . 1.383(2) ?
    C7 H7A . 0.9300 ?
    C10 C9 . 1.376(3) ?
    C10 H10A . 0.9300 ?
    C9 C8 . 1.380(3) ?
    C9 H9A . 0.9300 ?
    C8 H8A . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 S2 C4 . . 95.45(6) ?
    N1 S1 C1 . . 93.61(6) ?
    C2 O1 C1 . . 111.27(10) ?
    O2 C1 O1 . . 122.58(13) ?
    O2 C1 S1 . . 130.46(12) ?
    O1 C1 S1 . . 106.96(9) ?
    C4 C3 C5 . . 110.58(12) ?
    C4 C3 C2 . . 122.58(12) ?
    C5 C3 C2 . . 126.64(11) ?
    N1 C2 O1 . . 118.86(12) ?
    N1 C2 C3 . . 126.82(12) ?
    O1 C2 C3 . . 114.23(11) ?
    C5 N2 S2 . . 109.98(10) ?
    C2 N1 S1 . . 109.27(9) ?
    C3 C4 S2 . . 109.25(10) ?
    C3 C4 H4 . . 125.4 ?
    S2 C4 H4 . . 125.4 ?
    N2 C5 C3 . . 114.74(12) ?
    N2 C5 C6 . . 118.14(12) ?
    C3 C5 C6 . . 127.12(12) ?
    C7 C6 C11 . . 119.48(13) ?
    C7 C6 C5 . . 121.01(13) ?
    C11 C6 C5 . . 119.50(13) ?
    C6 C11 C10 . . 120.07(15) ?
    C6 C11 H11A . . 120.0 ?
    C10 C11 H11A . . 120.0 ?
    C8 C7 C6 . . 120.03(15) ?
    C8 C7 H7A . . 120.0 ?
    C6 C7 H7A . . 120.0 ?
    C9 C10 C11 . . 120.04(15) ?
    C9 C10 H10A . . 120.0 ?
    C11 C10 H10A . . 120.0 ?
    C10 C9 C8 . . 119.98(15) ?
    C10 C9 H9A . . 120.0 ?
    C8 C9 H9A . . 120.0 ?
    C9 C8 C7 . . 120.40(17) ?
    C9 C8 H8A . . 119.8 ?
    C7 C8 H8A . . 119.8 ?
data_ms003_0m
_journal_date_recd_electronic     2017-09-14
_journal_date_accepted     2017-10-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     11
_journal_page_first     1726
_journal_page_last     1731
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017015067
_journal_coeditor_code     HB7705
_publ_contact_author_name     "Schriver, Melbourne J."
_publ_contact_author_address
;
Department of Chemistry, Crandall University, PO Box 6004, Moncton,
New Brunswick, E1C 9L7
Canada
;
_publ_contact_author_email     mel.schriver@crandallu.ca
_publ_section_title
;
The crystal structures of two isomers of
5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhu, Shuguang' .
;
Teva Pharmaceuticals
3333 N Torrey Pines Ct,
Suite 400
La Jolla, CA 92130
;
    'Schriver, Melbourne J.' .
;
Department of Chemistry, Crandall University, PO Box 6004, Moncton,
New Brunswick, E1C 9L7
Canada
;
    'Hendsbee, Arthur D.' .
;
The Atlantic Centre for Green Chemistry and the Department of Chemistry,
Saint Mary's University, Halifax, Nova Scotia, B3H 3C3
Canada
;
    'Masuda, Jason D.' .
;
The Atlantic Centre for Green Chemistry and the Department of Chemistry,
Saint Mary's University, Halifax, Nova Scotia, B3H 3C3
Canada
;
_publ_section_synopsis
;
The 3,5-isomer of the title compound contains two almost planar molecules in
the asymmetric unit, whereas the 3,4-isomer contains a single substantially
twisted molecule. Both crystal structures feature short S...N and S...O
interactions.
;
