# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(S)-1-(6-chloro-2,2-dioxido-3,4-dihydrobenzo[e][1,2,3]oxathiazin-4-yl)propan-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cl N O4 S'
_chemical_formula_weight         275.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  p_2ac_2ab
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.3279(9)
_cell_length_b                   14.1730(17)
_cell_length_c                   22.626(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2349.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2432
_cell_measurement_theta_min      2.301
_cell_measurement_theta_max      19.804

_exptl_crystal_description       Needle-like
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   'SADABS(Bruker, 2005)'

_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  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14969
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         28.35
_reflns_number_total             5800
_reflns_number_gt                3716
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2(Bruker, 2005)'
_computing_cell_refinement       'APEX 2'
_computing_data_reduction        'SAINT(Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL(Bruker, 2005)'
_computing_publication_material  SHELXTL


_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)+(0.0423P)²] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_number_reflns         5800
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 -0.0321(5) 0.4184(2) 0.78016(12) 0.0404(8) Uani 1 1 d . . .
C2 C 0.1323(5) 0.4102(2) 0.75149(14) 0.0459(9) Uani 1 1 d . . .
H2 H 0.1396 0.4181 0.7108 0.055 Uiso 1 1 calc R . .
C3 C 0.2855(5) 0.3902(2) 0.78391(14) 0.0470(9) Uani 1 1 d . . .
H3 H 0.3980 0.3844 0.7652 0.056 Uiso 1 1 calc R . .
C4 C 0.2725(5) 0.3786(2) 0.84430(13) 0.0394(7) Uani 1 1 d . . .
C5 C 0.1083(4) 0.38517(19) 0.87382(12) 0.0352(7) Uani 1 1 d . . .
C6 C -0.0456(5) 0.4049(2) 0.84053(13) 0.0399(7) Uani 1 1 d . . .
H6 H -0.1588 0.4092 0.8589 0.048 Uiso 1 1 calc R . .
C7 C 0.0872(5) 0.3697(2) 0.94038(12) 0.0388(7) Uani 1 1 d . . .
H7 H -0.0040 0.3199 0.9460 0.047 Uiso 1 1 calc R . .
C8 C 0.0165(5) 0.4578(2) 0.97143(12) 0.0436(8) Uani 1 1 d . . .
H8A H 0.1134 0.5044 0.9726 0.052 Uiso 1 1 calc R . .
H8B H -0.0828 0.4841 0.9483 0.052 Uiso 1 1 calc R . .
C9 C -0.0499(4) 0.4406(2) 1.03322(12) 0.0399(7) Uani 1 1 d . . .
C10 C -0.0641(8) 0.5259(3) 1.07187(16) 0.0853(15) Uani 1 1 d . . .
H10A H -0.1478 0.5135 1.1036 0.128 Uiso 1 1 calc R . .
H10B H -0.1073 0.5783 1.0490 0.128 Uiso 1 1 calc R . .
H10C H 0.0539 0.5406 1.0879 0.128 Uiso 1 1 calc R . .
C11 C 0.3983(4) 0.3473(2) 0.18231(13) 0.0409(7) Uani 1 1 d . . .
C12 C 0.2285(5) 0.3461(3) 0.15597(15) 0.0548(9) Uani 1 1 d . . .
H12 H 0.2173 0.3476 0.1150 0.066 Uiso 1 1 calc R . .
C13 C 0.0767(5) 0.3426(3) 0.19124(14) 0.0564(9) Uani 1 1 d . . .
H13 H -0.0388 0.3414 0.1742 0.068 Uiso 1 1 calc R . .
C14 C 0.0944(4) 0.3408(2) 0.25181(13) 0.0404(7) Uani 1 1 d . . .
C15 C 0.2627(4) 0.33972(19) 0.27923(12) 0.0349(7) Uani 1 1 d . . .
C16 C 0.4160(4) 0.34373(19) 0.24278(12) 0.0372(7) Uani 1 1 d . . .
H16 H 0.5318 0.3440 0.2596 0.045 Uiso 1 1 calc R . .
C17 C 0.2861(4) 0.3358(2) 0.34607(13) 0.0377(7) Uani 1 1 d . . .
H17 H 0.3668 0.3880 0.3572 0.045 Uiso 1 1 calc R . .
C18 C 0.3772(4) 0.2450(2) 0.36672(12) 0.0390(7) Uani 1 1 d . . .
H18A H 0.2919 0.1932 0.3621 0.047 Uiso 1 1 calc R . .
H18B H 0.4816 0.2322 0.3416 0.047 Uiso 1 1 calc R . .
C19 C 0.4397(5) 0.2487(2) 0.43018(13) 0.0474(8) Uani 1 1 d . . .
C20 C 0.5328(7) 0.1614(3) 0.45304(17) 0.0849(14) Uani 1 1 d . . .
H20A H 0.5390 0.1639 0.4954 0.127 Uiso 1 1 calc R . .
H20B H 0.6540 0.1578 0.4371 0.127 Uiso 1 1 calc R . .
H20C H 0.4648 0.1067 0.4412 0.127 Uiso 1 1 calc R . .
Cl1 Cl -0.22683(13) 0.44416(7) 0.73976(4) 0.0624(3) Uani 1 1 d . . .
Cl2 Cl 0.58844(12) 0.35625(6) 0.13729(3) 0.0537(2) Uani 1 1 d . . .
N1 N 0.2610(4) 0.33591(18) 0.96731(10) 0.0420(6) Uani 1 1 d . . .
H1 H 0.2618 0.2944 0.9950 0.050 Uiso 1 1 calc R . .
N2 N 0.1116(4) 0.35081(19) 0.37658(11) 0.0484(7) Uani 1 1 d . . .
H2A H 0.1072 0.3833 0.4086 0.058 Uiso 1 1 calc R . .
O1 O -0.0909(3) 0.36371(15) 1.05074(8) 0.0455(5) Uani 1 1 d . . .
O2 O 0.5987(3) 0.33049(17) 0.96346(11) 0.0630(7) Uani 1 1 d . . .
O3 O 0.4365(4) 0.47949(14) 0.94814(10) 0.0576(6) Uani 1 1 d . . .
O4 O 0.4373(3) 0.35667(16) 0.87354(8) 0.0525(6) Uani 1 1 d . . .
O5 O 0.4183(4) 0.31666(18) 0.46058(9) 0.0630(7) Uani 1 1 d . . .
O6 O -0.2244(3) 0.3471(2) 0.37580(12) 0.0782(8) Uani 1 1 d . . .
O7 O -0.0512(4) 0.20699(16) 0.34555(10) 0.0637(7) Uani 1 1 d . . .
O8 O -0.0713(3) 0.34356(17) 0.28320(9) 0.0564(6) Uani 1 1 d . . .
S1 S 0.44448(13) 0.38009(6) 0.94235(4) 0.0462(2) Uani 1 1 d . . .
S2 S -0.06960(13) 0.30592(7) 0.34938(4) 0.0512(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 C2 1.373(4) . ?
C1 C6 1.383(4) . ?
C1 Cl1 1.733(3) . ?
C2 C3 1.371(5) . ?
C3 C4 1.379(4) . ?
C4 C5 1.379(4) . ?
C4 O4 1.412(4) . ?
C5 C6 1.384(4) . ?
C5 C7 1.530(4) . ?
C7 N1 1.491(4) . ?
C7 C8 1.524(4) . ?
C8 C9 1.500(4) . ?
C9 O1 1.198(4) . ?
C9 C10 1.495(4) . ?
C11 C16 1.375(4) . ?
C11 C12 1.380(4) . ?
C11 Cl2 1.731(3) . ?
C12 C13 1.370(5) . ?
C13 C14 1.377(4) . ?
C14 C15 1.380(4) . ?
C14 O8 1.408(4) . ?
C15 C16 1.395(4) . ?
C15 C17 1.523(4) . ?
C17 N2 1.469(4) . ?
C17 C18 1.523(4) . ?
C18 C19 1.508(4) . ?
C19 O5 1.194(4) . ?
C19 C20 1.505(5) . ?
N1 S1 1.587(3) . ?
N2 S2 1.596(3) . ?
O2 S1 1.414(3) . ?
O3 S1 1.416(2) . ?
O4 S1 1.593(2) . ?
O6 S2 1.409(3) . ?
O7 S2 1.411(2) . ?
O8 S2 1.590(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
C2 C1 C6 121.2(3) . . ?
C2 C1 Cl1 119.4(2) . . ?
C6 C1 Cl1 119.4(3) . . ?
C3 C2 C1 118.9(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 O4 115.5(3) . . ?
C5 C4 O4 122.3(2) . . ?
C4 C5 C6 117.4(2) . . ?
C4 C5 C7 123.7(3) . . ?
C6 C5 C7 118.9(3) . . ?
C1 C6 C5 120.5(3) . . ?
N1 C7 C8 111.5(2) . . ?
N1 C7 C5 111.2(3) . . ?
C8 C7 C5 111.8(2) . . ?
C9 C8 C7 114.0(2) . . ?
O1 C9 C10 121.6(3) . . ?
O1 C9 C8 122.5(3) . . ?
C10 C9 C8 115.9(3) . . ?
C16 C11 C12 121.0(3) . . ?
C16 C11 Cl2 120.8(2) . . ?
C12 C11 Cl2 118.2(2) . . ?
C13 C12 C11 118.8(3) . . ?
C12 C13 C14 120.2(3) . . ?
C13 C14 C15 122.1(3) . . ?
C13 C14 O8 114.8(3) . . ?
C15 C14 O8 123.0(3) . . ?
C14 C15 C16 117.0(3) . . ?
C14 C15 C17 123.2(3) . . ?
C16 C15 C17 119.9(3) . . ?
C11 C16 C15 120.9(3) . . ?
N2 C17 C18 111.1(3) . . ?
N2 C17 C15 111.3(2) . . ?
C18 C17 C15 112.6(2) . . ?
C19 C18 C17 113.3(3) . . ?
O5 C19 C20 121.7(3) . . ?
O5 C19 C18 122.5(3) . . ?
C20 C19 C18 115.9(3) . . ?
C7 N1 S1 116.84(19) . . ?
C17 N2 S2 119.0(2) . . ?
C4 O4 S1 116.11(18) . . ?
C14 O8 S2 117.31(19) . . ?
O2 S1 O3 119.76(17) . . ?
O2 S1 N1 111.15(14) . . ?
O3 S1 N1 108.94(16) . . ?
O2 S1 O4 104.65(15) . . ?
O3 S1 O4 107.25(13) . . ?
N1 S1 O4 103.75(13) . . ?
O6 S2 O7 120.95(18) . . ?
O6 S2 O8 104.74(16) . . ?
O7 S2 O8 106.04(14) . . ?
O6 S2 N2 109.94(15) . . ?
O7 S2 N2 109.91(16) . . ?
O8 S2 N2 103.66(14) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_database_code_depnum_ccdc_archive 'CCDC 1016210'
