# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_jww_160815
_database_code_depnum_ccdc_archive 'CCDC 1509110'
_audit_update_record             
;
2016-10-10 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_audit_creation_date             2016-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C16 H12 O5 S'
_chemical_formula_sum            'C16 H12 O5 S'
_chemical_formula_weight         316.34
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.99567(15)
_cell_length_b                   20.3803(3)
_cell_length_c                   8.08882(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.5457(16)
_cell_angle_gamma                90
_cell_volume                     1447.55(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4932
_cell_measurement_theta_max      72.0530
_cell_measurement_theta_min      2.1920
_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4514
_exptl_crystal_F_000             659.5614
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6373
_diffrn_reflns_theta_full        72.3225
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.34
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9583
_diffrn_measured_fraction_theta_max 0.9583
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00 114.00   1.00    2.00    --   44.52  57.00   0.00   95
  2  ω     85.00 114.00   1.00    2.00    --   44.52 125.00 120.00   29
  3  ω     30.00 119.00   1.00    3.00    --  100.00 -45.00  60.00   89
  4  ω     33.00 114.00   1.00    3.00    --  100.00-125.00 -60.00   81
  5  ω     27.00 121.00   1.00    3.00    --  100.00-125.00 -30.00   94
  6  ω     69.00 160.00   1.00    3.00    --  100.00  77.00-150.00   91
  7  ω     73.00  98.00   1.00    2.00    --   44.52 125.00-180.00   25
  8  ω   -115.00 -84.00   1.00    2.00    --  -44.52-125.00   0.00   31
  9  ω   -125.00-100.00   1.00    2.00    --  -44.52 -99.00  60.00   25
 10  ω   -141.00-115.00   1.00    3.00    --  -90.00 -45.00   0.00   26
 11  ω   -144.00 -86.00   1.00    3.00    --  -90.00 -61.00 -60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1450441000
_diffrn_orient_matrix_UB_12      0.0373045000
_diffrn_orient_matrix_UB_13      -0.0865989000
_diffrn_orient_matrix_UB_21      -0.0951014000
_diffrn_orient_matrix_UB_22      -0.0432604000
_diffrn_orient_matrix_UB_23      0.0942805000
_diffrn_orient_matrix_UB_31      0.0260816000
_diffrn_orient_matrix_UB_32      0.0495648000
_diffrn_orient_matrix_UB_33      0.1471957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2536
_reflns_number_total             2732
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3160
_refine_diff_density_min         -0.4892
_refine_diff_density_rms         0.0566
_refine_ls_d_res_high            0.8091
_refine_ls_d_res_low             10.1901
_refine_ls_goodness_of_fit_ref   1.0436
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.0436
_refine_ls_shift/su_max          0.0864
_refine_ls_shift/su_mean         0.0014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.5779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1099
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C13(H13), C8(H8), C9(H9), C21(H21), C1(H1), C19(H19),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.25887(5) 0.494535(19) 0.79484(5) 0.02527(15) Uani 1.000000 .
O2 O 0.39032(13) 0.44420(6) 0.88604(14) 0.0261(3) Uani 1.000000 .
O3 O 0.15505(15) 0.49222(6) 0.90447(16) 0.0322(3) Uani 1.000000 .
O4 O 0.71559(13) 0.37390(6) 0.75763(16) 0.0284(3) Uani 1.000000 .
O5 O 0.87112(14) 0.29069(6) 0.72240(18) 0.0366(3) Uani 1.000000 .
O6 O 0.33074(15) 0.55446(6) 0.76526(16) 0.0324(3) Uani 1.000000 .
C7 C 0.52127(19) 0.43961(8) 0.8203(2) 0.0261(4) Uani 1.000000 .
C8 C 0.21647(19) 0.48150(9) 0.4542(2) 0.0280(4) Uani 1.000000 .
C9 C 0.6146(2) 0.20300(9) 0.8213(2) 0.0328(4) Uani 1.000000 .
C10 C 0.18335(18) 0.45617(8) 0.6016(2) 0.0246(3) Uani 1.000000 .
C11 C 0.0119(2) 0.35914(10) 0.1293(2) 0.0362(4) Uani 1.000000 .
C12 C 0.09269(19) 0.40070(8) 0.5987(2) 0.0273(4) Uani 1.000000 .
C13 C 0.1592(2) 0.44992(9) 0.3026(2) 0.0298(4) Uani 1.000000 .
C14 C 0.07091(19) 0.39330(8) 0.2958(2) 0.0275(4) Uani 1.000000 .
C15 C 0.75452(19) 0.30778(9) 0.7581(2) 0.0285(4) Uani 1.000000 .
C16 C 0.52428(19) 0.31481(8) 0.8411(2) 0.0267(4) Uani 1.000000 .
C17 C 0.57761(19) 0.38024(8) 0.8083(2) 0.0259(4) Uani 1.000000 .
C18 C 0.03750(19) 0.36960(8) 0.4455(2) 0.0285(4) Uani 1.000000 .
C19 C 0.3945(2) 0.29295(9) 0.8921(2) 0.0309(4) Uani 1.000000 .
C20 C 0.63178(19) 0.27054(9) 0.8084(2) 0.0275(4) Uani 1.000000 .
C21 C 0.4844(2) 0.18124(9) 0.8700(3) 0.0364(4) Uani 1.000000 .
C1 C 0.3776(2) 0.22546(10) 0.9056(3) 0.0361(4) Uani 1.000000 .
H12 H 0.06957(19) 0.38479(8) 0.6979(2) 0.0328(4) Uiso 1.000000 R
H18 H -0.02276(19) 0.33234(8) 0.4422(2) 0.0342(5) Uiso 1.000000 R
H13 H 0.1798(2) 0.46674(9) 0.2031(2) 0.0357(5) Uiso 1.000000 R
H8 H 0.27604(19) 0.51897(9) 0.4575(2) 0.0336(4) Uiso 1.000000 R
H9 H 0.6871(2) 0.17383(9) 0.7985(2) 0.0394(5) Uiso 1.000000 R
H21 H 0.4682(2) 0.13644(9) 0.8789(3) 0.0437(5) Uiso 1.000000 R
H1 H 0.2922(2) 0.20934(10) 0.9395(3) 0.0434(5) Uiso 1.000000 R
H19 H 0.3225(2) 0.32214(9) 0.9160(2) 0.0370(5) Uiso 1.000000 R
H7 H 0.56693(19) 0.47671(8) 0.7863(2) 0.0313(4) Uiso 1.000000 R
H11a H -0.0097(17) 0.39108(12) 0.0400(4) 0.0543(6) Uiso 1.000000 GR
H11b H 0.0873(7) 0.3289(6) 0.1077(10) 0.0543(6) Uiso 1.000000 GR
H11c H -0.0796(10) 0.3356(6) 0.1341(7) 0.0543(6) Uiso 1.000000 GR


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 1.6174(12) . ?
S1 O3 1.4214(13) . ?
S1 O6 1.4262(13) . ?
S1 C10 1.7477(17) . ?
O2 C7 1.3969(19) . ?
O4 C15 1.392(2) . ?
O4 C17 1.3952(19) . ?
O5 C15 1.198(2) . ?
C7 C17 1.323(2) . ?
C7 H7 0.9300 . ?
C8 C10 1.390(2) . ?
C8 C13 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C20 1.392(2) . ?
C9 C21 1.387(3) . ?
C9 H9 0.9300 . ?
C10 C12 1.391(2) . ?
C11 C14 1.507(2) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C12 C18 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(2) . ?
C13 H13 0.9300 . ?
C14 C18 1.395(2) . ?
C15 C20 1.468(2) . ?
C16 C17 1.461(2) . ?
C16 C19 1.393(2) . ?
C16 C20 1.389(2) . ?
C18 H18 0.9300 . ?
C19 C1 1.391(3) . ?
C19 H19 0.9300 . ?
C21 C1 1.392(3) . ?
C21 H21 0.9300 . ?
C1 H1 0.9300 . ?

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
O3 S1 O2 102.05(7) . . ?
O6 S1 O2 107.85(7) . . ?
O6 S1 O3 121.08(8) . . ?
C10 S1 O2 103.17(7) . . ?
C10 S1 O3 111.27(8) . . ?
C10 S1 O6 109.59(8) . . ?
C7 O2 S1 117.54(10) . . ?
C17 O4 C15 109.16(12) . . ?
C17 C7 O2 117.20(15) . . ?
H7 C7 O2 121.40(8) . . ?
H7 C7 C17 121.40(10) . . ?
C13 C8 C10 118.70(16) . . ?
H8 C8 C10 120.65(10) . . ?
H8 C8 C13 120.65(10) . . ?
C21 C9 C20 116.86(17) . . ?
H9 C9 C20 121.57(11) . . ?
H9 C9 C21 121.57(11) . . ?
C8 C10 S1 119.15(13) . . ?
C12 C10 S1 119.44(13) . . ?
C12 C10 C8 121.41(16) . . ?
H11a C11 C14 109.5 . . ?
H11b C11 C14 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C14 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C18 C12 C10 118.84(16) . . ?
H12 C12 C10 120.58(10) . . ?
H12 C12 C18 120.58(10) . . ?
C14 C13 C8 121.30(16) . . ?
H13 C13 C8 119.35(10) . . ?
H13 C13 C14 119.35(10) . . ?
C13 C14 C11 120.29(16) . . ?
C18 C14 C11 121.00(16) . . ?
C18 C14 C13 118.71(16) . . ?
O5 C15 O4 120.89(15) . . ?
C20 C15 O4 107.28(14) . . ?
C20 C15 O5 131.82(17) . . ?
C19 C16 C17 132.46(16) . . ?
C20 C16 C17 106.78(15) . . ?
C20 C16 C19 120.75(16) . . ?
C7 C17 O4 119.04(15) . . ?
C16 C17 O4 108.48(14) . . ?
C16 C17 C7 132.47(16) . . ?
C14 C18 C12 121.00(16) . . ?
H18 C18 C12 119.50(10) . . ?
H18 C18 C14 119.50(10) . . ?
C1 C19 C16 116.91(17) . . ?
H19 C19 C16 121.55(10) . . ?
H19 C19 C1 121.55(11) . . ?
C15 C20 C9 129.37(16) . . ?
C16 C20 C9 122.34(16) . . ?
C16 C20 C15 108.27(15) . . ?
C1 C21 C9 121.00(17) . . ?
H21 C21 C9 119.50(11) . . ?
H21 C21 C1 119.50(11) . . ?
C21 C1 C19 122.12(17) . . ?
H1 C1 C19 118.94(11) . . ?
H1 C1 C21 118.94(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 39.314
_oxdiff_exptl_absorpt_empirical_full_min 0.537
_chemical_name_systematic        
'(E)-(3-oxoisobenzofuran-1(3H)-ylidene)methyl 4-methylbenzenesulfonate'
_exptl_crystal_colour            white
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/petroleum ether'
####################################################################### 
# 
# 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_jww_160908
_database_code_depnum_ccdc_archive 'CCDC 1509109'
_audit_update_record             
;
2016-10-10 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         '0.44(C23 N O6 S2)'
_chemical_formula_sum            'C10.222 N0.444 O2.667 S0.889'
_chemical_formula_weight         200.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.83191(19)
_cell_length_b                   12.3569(3)
_cell_length_c                   22.7654(5)
_cell_angle_alpha                104.4355(19)
_cell_angle_beta                 97.8284(19)
_cell_angle_gamma                93.8331(19)
_cell_volume                     2102.05(9)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    9529
_cell_measurement_theta_max      71.8960
_cell_measurement_theta_min      2.0140
_exptl_absorpt_coefficient_mu    2.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4230
_exptl_crystal_F_000             905.7473
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16920
_diffrn_reflns_theta_full        72.3161
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         2.03
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9646
_diffrn_measured_fraction_theta_max 0.9646
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  54.00   1.00    3.00    --   44.40 -57.00  60.00   68
  2  ω     28.00  77.00   1.00   10.00    --  100.00 -77.00  90.00   49
  3  ω     98.00 125.00   1.00   10.00    --  100.00 -77.00  90.00   27
  4  ω    106.00 138.00   1.00   10.00    --  100.00 -15.00   0.00   32
  5  ω     84.00 161.00   1.00   10.00    --  100.00  45.00 -90.00   77
  6  ω     80.00 158.00   1.00   10.00    --  100.00  61.00-180.00   78
  7  ω     41.00  68.00   1.00   10.00    --  100.00 -94.00  60.00   27
  8  ω     22.00  88.00   1.00   10.00    --  100.00 -94.00 150.00   66
  9  ω     17.00 108.00   1.00   10.00    --  100.00 -94.00  30.00   91
 10  ω     29.00  55.00   1.00   10.00    --  100.00 -45.00 -60.00   26
 11  ω     21.00  70.00   1.00   10.00    --  100.00 -15.00   0.00   49
 12  ω     22.00 113.00   1.00    3.00    --   44.40  57.00 -30.00   91
 13  ω     23.00 105.00   1.00   10.00    --  100.00 -94.00-120.00   82
 14  ω     96.00 121.00   1.00   10.00    --  100.00-125.00-150.00   25
 15  ω     18.00 104.00   1.00   10.00    --  100.00 -94.00 -30.00   86
 16  ω    -25.00  69.00   1.00    3.00    --   44.40 -57.00-180.00   94
 17  ω    -76.00 -51.00   1.00   10.00    --  -90.00 -15.00 150.00   25
 18  ω   -102.00 -72.00   1.00   10.00    --  -90.00  45.00   0.00   30
 19  ω   -166.00-105.00   1.00   10.00    --  -90.00 -15.00 150.00   61
 20  ω   -117.00 -75.00   1.00    3.00    --  -44.40-125.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0822163000
_diffrn_orient_matrix_UB_12      -0.0689327000
_diffrn_orient_matrix_UB_13      0.0421473000
_diffrn_orient_matrix_UB_21      -0.1703219000
_diffrn_orient_matrix_UB_22      -0.0780951000
_diffrn_orient_matrix_UB_23      -0.0135245000
_diffrn_orient_matrix_UB_31      0.0639890000
_diffrn_orient_matrix_UB_32      -0.0768600000
_diffrn_orient_matrix_UB_33      -0.0552169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                7361
_reflns_number_total             8035
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.5450
_refine_diff_density_min         -1.6893
_refine_diff_density_rms         0.1385
_refine_ls_d_res_high            0.8092
_refine_ls_d_res_low             21.7690
_refine_ls_goodness_of_fit_ref   0.9913
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     256
_refine_ls_number_reflns         8035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0899
_refine_ls_restrained_S_all      0.9913
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1541P)²+8.3811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2412
_refine_ls_wR_factor_ref         0.2468
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.84590(11) 0.76204(8) 0.56642(4) 0.0206(2) Uiso 1.000000 .
S2 S 0.04230(12) 0.48922(8) 0.83109(4) 0.0244(2) Uiso 1.000000 .
S3 S 0.88256(12) 1.07301(8) 0.78858(4) 0.0224(2) Uiso 1.000000 .
S4 S 0.28256(12) 0.93857(8) 0.87860(4) 0.0231(2) Uiso 1.000000 .
O5 O 0.9528(4) 0.8665(2) 0.59102(13) 0.0259(6) Uiso 1.000000 .
O6 O 1.0307(4) 1.1177(3) 0.76874(14) 0.0302(7) Uiso 1.000000 .
O0aa O 0.1311(4) 0.9375(3) 0.90716(14) 0.0294(6) Uiso 1.000000 .
O8 O 0.9014(4) 0.6737(2) 0.52244(13) 0.0269(6) Uiso 1.000000 .
O1aa O 0.0050(4) 0.5836(3) 0.87683(14) 0.0291(6) Uiso 1.000000 .
O2aa O 0.0022(4) 0.3662(3) 0.69282(15) 0.0337(7) Uiso 1.000000 .
O11 O 0.6841(4) 0.5342(2) 0.57000(14) 0.0285(6) Uiso 1.000000 .
O12 O 0.3376(4) 1.0315(3) 0.85732(14) 0.0309(7) Uiso 1.000000 .
O13 O 0.8629(4) 1.1003(3) 0.85176(14) 0.0310(7) Uiso 1.000000 .
O14 O -0.0779(4) 0.3909(3) 0.80914(14) 0.0317(7) Uiso 1.000000 .
N15 N 0.0696(4) 0.5374(3) 0.76945(16) 0.0242(7) Uiso 1.000000 .
N16 N 0.8172(4) 0.7115(3) 0.62701(15) 0.0198(6) Uiso 1.000000 .
C17 C 0.4188(5) 0.8398(3) 0.96591(19) 0.0254(8) Uiso 1.000000 .
O18 O 0.8795(4) 0.9379(2) 0.77190(13) 0.0245(6) Uiso 1.000000 .
O19 O 0.2496(4) 0.8360(2) 0.81614(13) 0.0259(6) Uiso 1.000000 .
C20 C 0.7041(5) 1.1680(4) 0.7071(2) 0.0278(9) Uiso 1.000000 .
C21 C 0.4535(5) 0.8986(3) 0.92330(18) 0.0225(8) Uiso 1.000000 .
C22 C 0.7169(5) 0.7234(3) 0.78230(19) 0.0255(8) Uiso 1.000000 .
C23 C 0.2727(5) 0.7197(3) 0.68625(18) 0.0228(8) Uiso 1.000000 .
C24 C 0.1358(5) 0.5322(3) 0.67297(18) 0.0214(8) Uiso 1.000000 .
C25 C 0.5822(5) 0.8937(3) 0.56176(19) 0.0246(8) Uiso 1.000000 .
C26 C 0.7408(5) 0.7051(3) 0.72107(17) 0.0205(7) Uiso 1.000000 .
C27 C 0.8210(5) 0.7793(3) 0.68904(17) 0.0187(7) Uiso 1.000000 .
C28 C 0.5514(6) 1.1842(4) 0.6727(2) 0.0333(10) Uiso 1.000000 .
C29 C 0.6938(5) 1.0919(3) 0.74248(18) 0.0217(8) Uiso 1.000000 .
C30 C 0.3624(5) 0.5315(4) 0.9012(2) 0.0279(9) Uiso 1.000000 .
C31 C 0.0595(5) 0.4635(3) 0.70895(18) 0.0229(8) Uiso 1.000000 .
C32 C 0.5224(6) 0.5013(4) 0.9227(2) 0.0296(9) Uiso 1.000000 .
C33 C 0.8901(5) 0.8857(3) 0.71083(18) 0.0221(8) Uiso 1.000000 .
C34 C 0.6380(5) 0.7890(3) 0.53819(18) 0.0214(8) Uiso 1.000000 .
C35 C 0.1944(5) 0.6396(3) 0.71086(17) 0.0192(7) Uiso 1.000000 .
C36 C 0.6855(5) 0.6012(3) 0.67955(18) 0.0215(8) Uiso 1.000000 .
C37 C 0.1527(5) 0.6466(3) 0.77236(18) 0.0207(7) Uiso 1.000000 .
C38 C 0.2900(5) 0.6879(4) 0.62425(19) 0.0258(8) Uiso 1.000000 .
C39 C 0.7234(5) 0.6041(3) 0.61849(18) 0.0211(7) Uiso 1.000000 .
C40 C 0.3126(5) 0.8347(3) 0.48986(19) 0.0246(8) Uiso 1.000000 .
C41 C 0.1708(5) 0.7348(3) 0.82069(18) 0.0232(8) Uiso 1.000000 .
C42 C 0.5565(6) 0.8014(4) 0.9981(2) 0.0294(9) Uiso 1.000000 .
C43 C 0.2297(5) 0.5795(3) 0.58688(19) 0.0243(8) Uiso 1.000000 .
C44 C 0.5378(5) 1.0330(4) 0.7447(2) 0.0276(9) Uiso 1.000000 .
C45 C 0.4194(5) 0.9155(4) 0.53744(19) 0.0263(8) Uiso 1.000000 .
C46 C 0.3878(6) 1.0511(4) 0.7104(2) 0.0323(9) Uiso 1.000000 .
C47 C 0.1513(5) 0.5002(3) 0.61147(19) 0.0248(8) Uiso 1.000000 .
C48 C 0.5813(6) 0.5302(4) 0.7575(2) 0.0313(9) Uiso 1.000000 .
C49 C 0.6231(6) 0.9235(4) 0.9140(2) 0.0294(9) Uiso 1.000000 .
C50 C 0.2891(6) 0.3432(4) 0.8333(2) 0.0302(9) Uiso 1.000000 .
C51 C 0.5673(6) 0.3924(4) 0.9011(2) 0.0290(9) Uiso 1.000000 .
C52 C 0.6371(6) 0.6353(4) 0.7997(2) 0.0298(9) Uiso 1.000000 .
C53 C 0.5326(5) 0.7052(3) 0.49224(19) 0.0243(8) Uiso 1.000000 .
C54 C 0.6054(5) 0.5123(4) 0.6961(2) 0.0274(9) Uiso 1.000000 .
C1 C 0.7265(6) 0.8209(4) 0.9877(2) 0.0320(9) Uiso 1.000000 .
C2 C 0.2463(5) 0.4521(3) 0.85635(19) 0.0238(8) Uiso 1.000000 .
C3 C 0.3702(5) 0.7290(4) 0.4688(2) 0.0263(8) Uiso 1.000000 .
C4 C 0.7574(6) 0.8843(4) 0.9467(2) 0.0351(10) Uiso 1.000000 .
C5 C 0.3918(6) 1.1274(4) 0.6742(2) 0.0301(9) Uiso 1.000000 .
C6 C 0.2263(7) 1.1467(5) 0.6376(3) 0.0423(11) Uiso 1.000000 .
C7 C 0.1417(6) 0.8611(4) 0.4615(2) 0.0311(9) Uiso 1.000000 .
C8 C 0.7388(6) 0.3604(4) 0.9272(2) 0.0387(11) Uiso 1.000000 .
C9 C 0.4504(6) 0.3141(4) 0.8558(2) 0.0324(9) Uiso 1.000000 .
C10 C 0.8728(7) 0.7750(5) 1.0211(3) 0.0466(12) Uiso 1.000000 .

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 O5 1.431(3) . ?
S1 O8 1.422(3) . ?
S1 N16 1.685(3) . ?
S1 C34 1.752(4) . ?
S2 O1aa 1.433(3) . ?
S2 O14 1.424(3) . ?
S2 N15 1.689(3) . ?
S2 C2 1.753(4) . ?
S3 O6 1.427(3) . ?
S3 O13 1.425(3) . ?
S3 O18 1.615(3) . ?
S3 C29 1.757(4) . ?
S4 O0aa 1.429(3) . ?
S4 O12 1.417(3) . ?
S4 O19 1.629(3) . ?
S4 C21 1.744(4) . ?
O2aa C31 1.202(5) . ?
O11 C39 1.207(5) . ?
N15 C31 1.439(5) . ?
N15 C37 1.441(5) . ?
N16 C27 1.446(5) . ?
N16 C39 1.429(5) . ?
C17 C21 1.392(6) . ?
C17 C42 1.397(6) . ?
O18 C33 1.395(5) . ?
O19 C41 1.391(5) . ?
C20 C28 1.393(6) . ?
C20 C29 1.388(6) . ?
C21 C49 1.400(6) . ?
C22 C26 1.396(6) . ?
C22 C52 1.387(6) . ?
C23 C35 1.400(5) . ?
C23 C38 1.396(6) . ?
C24 C31 1.470(5) . ?
C24 C35 1.398(5) . ?
C24 C47 1.381(6) . ?
C25 C34 1.396(6) . ?
C25 C45 1.390(6) . ?
C26 C27 1.466(5) . ?
C26 C36 1.392(5) . ?
C27 C33 1.332(5) . ?
C28 C5 1.401(6) . ?
C29 C44 1.393(6) . ?
C30 C32 1.392(6) . ?
C30 C2 1.400(6) . ?
C32 C51 1.399(6) . ?
C34 C53 1.399(6) . ?
C35 C37 1.463(5) . ?
C36 C39 1.469(5) . ?
C36 C54 1.386(6) . ?
C37 C41 1.325(6) . ?
C38 C43 1.407(6) . ?
C40 C45 1.404(6) . ?
C40 C3 1.402(6) . ?
C40 C7 1.498(6) . ?
C42 C1 1.400(6) . ?
C43 C47 1.392(6) . ?
C44 C46 1.382(6) . ?
C46 C5 1.400(6) . ?
C48 C52 1.410(6) . ?
C48 C54 1.400(6) . ?
C49 C4 1.389(6) . ?
C50 C2 1.398(6) . ?
C50 C9 1.401(6) . ?
C51 C8 1.512(6) . ?
C51 C9 1.402(6) . ?
C53 C3 1.390(6) . ?
C1 C4 1.395(7) . ?
C1 C10 1.509(7) . ?
C5 C6 1.510(7) . ?

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
O8 S1 O5 120.33(17) . . ?
N16 S1 O5 106.00(16) . . ?
N16 S1 O8 106.68(17) . . ?
C34 S1 O5 108.94(17) . . ?
C34 S1 O8 109.53(18) . . ?
C34 S1 N16 104.10(17) . . ?
O14 S2 O1aa 120.57(18) . . ?
N15 S2 O1aa 106.00(18) . . ?
N15 S2 O14 106.56(18) . . ?
C2 S2 O1aa 108.29(19) . . ?
C2 S2 O14 109.52(19) . . ?
C2 S2 N15 104.73(18) . . ?
O13 S3 O6 121.40(19) . . ?
O18 S3 O6 108.34(17) . . ?
O18 S3 O13 102.39(17) . . ?
C29 S3 O6 109.33(18) . . ?
C29 S3 O13 110.95(18) . . ?
C29 S3 O18 102.52(17) . . ?
O12 S4 O0aa 121.37(18) . . ?
O19 S4 O0aa 107.71(17) . . ?
O19 S4 O12 102.54(17) . . ?
C21 S4 O0aa 109.42(18) . . ?
C21 S4 O12 111.24(19) . . ?
C21 S4 O19 102.60(17) . . ?
C31 N15 S2 122.3(3) . . ?
C37 N15 S2 124.8(3) . . ?
C37 N15 C31 110.6(3) . . ?
C27 N16 S1 125.1(3) . . ?
C39 N16 S1 120.9(3) . . ?
C39 N16 C27 110.2(3) . . ?
C42 C17 C21 118.9(4) . . ?
C33 O18 S3 115.6(2) . . ?
C41 O19 S4 116.1(3) . . ?
C29 C20 C28 117.7(4) . . ?
C17 C21 S4 119.7(3) . . ?
C49 C21 S4 118.8(3) . . ?
C49 C21 C17 121.4(4) . . ?
C52 C22 C26 117.8(4) . . ?
C38 C23 C35 117.9(4) . . ?
C35 C24 C31 109.4(3) . . ?
C47 C24 C31 127.5(4) . . ?
C47 C24 C35 123.1(4) . . ?
C45 C25 C34 118.7(4) . . ?
C27 C26 C22 130.9(4) . . ?
C36 C26 C22 120.3(4) . . ?
C36 C26 C27 108.8(3) . . ?
C26 C27 N16 105.5(3) . . ?
C33 C27 N16 125.3(3) . . ?
C33 C27 C26 129.1(4) . . ?
C5 C28 C20 121.5(4) . . ?
C20 C29 S3 118.9(3) . . ?
C44 C29 S3 118.6(3) . . ?
C44 C29 C20 122.4(4) . . ?
C2 C30 C32 119.3(4) . . ?
N15 C31 O2aa 126.2(4) . . ?
C24 C31 O2aa 128.6(4) . . ?
C24 C31 N15 105.2(3) . . ?
C51 C32 C30 121.0(4) . . ?
C27 C33 O18 117.1(3) . . ?
C25 C34 S1 119.2(3) . . ?
C53 C34 S1 119.2(3) . . ?
C53 C34 C25 121.6(4) . . ?
C24 C35 C23 119.5(4) . . ?
C37 C35 C23 131.4(3) . . ?
C37 C35 C24 109.1(3) . . ?
C39 C36 C26 109.6(3) . . ?
C54 C36 C26 122.7(4) . . ?
C54 C36 C39 127.6(4) . . ?
C35 C37 N15 105.7(3) . . ?
C41 C37 N15 124.7(4) . . ?
C41 C37 C35 129.4(4) . . ?
C43 C38 C23 121.7(4) . . ?
N16 C39 O11 125.1(4) . . ?
C36 C39 O11 129.5(4) . . ?
C36 C39 N16 105.4(3) . . ?
C3 C40 C45 118.6(4) . . ?
C7 C40 C45 120.9(4) . . ?
C7 C40 C3 120.5(4) . . ?
C37 C41 O19 118.3(4) . . ?
C1 C42 C17 120.8(4) . . ?
C47 C43 C38 120.2(4) . . ?
C46 C44 C29 118.8(4) . . ?
C40 C45 C25 121.2(4) . . ?
C5 C46 C44 120.8(4) . . ?
C43 C47 C24 117.7(4) . . ?
C54 C48 C52 120.2(4) . . ?
C4 C49 C21 118.4(4) . . ?
C9 C50 C2 119.1(4) . . ?
C8 C51 C32 119.9(4) . . ?
C9 C51 C32 119.0(4) . . ?
C9 C51 C8 121.0(4) . . ?
C48 C52 C22 121.8(4) . . ?
C3 C53 C34 118.5(4) . . ?
C48 C54 C36 117.2(4) . . ?
C4 C1 C42 118.7(4) . . ?
C10 C1 C42 120.1(4) . . ?
C10 C1 C4 121.1(4) . . ?
C30 C2 S2 119.1(3) . . ?
C50 C2 S2 120.0(3) . . ?
C50 C2 C30 120.8(4) . . ?
C53 C3 C40 121.3(4) . . ?
C1 C4 C49 121.6(4) . . ?
C46 C5 C28 118.7(4) . . ?
C6 C5 C28 121.3(4) . . ?
C6 C5 C46 120.0(4) . . ?
C51 C9 C50 120.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.624
_chemical_name_systematic        
'(E)-(3-oxo-2-tosylisoindolin-1-ylidene)methyl 4-methylbenzenesulfonate'
_exptl_crystal_colour            white
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/petroleum ether'
