# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1912765'
loop_
_audit_author_name
_audit_author_address
'Guoqiang Li'
;South China University of Technology
China
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl N O3 S'
_chemical_formula_sum            'C15 H10 Cl N O3 S'
_chemical_formula_weight         319.75
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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_IT_number           2
_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                   7.0797(4)
_cell_length_b                   8.5758(5)
_cell_length_c                   10.9983(6)
_cell_angle_alpha                93.142(5)
_cell_angle_beta                 91.207(4)
_cell_angle_gamma                91.822(5)
_cell_volume                     666.24(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8570
_cell_measurement_theta_min      2.3760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9057
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.438
_diffrn_reflns_theta_min         2.380
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  17.00   1.00    1.00    --  -11.59 -57.00 150.00  102
  2  ω    -40.00  62.00   1.00    1.00    --  -11.59  57.00 -60.00  102
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00  90.00  101
  4  ω     28.00  94.00   1.00    1.00    --   11.74-170.00 -54.00   66
  5  ω    -20.00   5.00   1.00    1.00    --   11.74 -99.00  60.00   25
  6  ω    -63.00  36.00   1.00    1.00    --   11.74 -37.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0050719000
_diffrn_orient_matrix_UB_12      0.0577516000
_diffrn_orient_matrix_UB_13      -0.0436132000
_diffrn_orient_matrix_UB_21      0.0215665000
_diffrn_orient_matrix_UB_22      0.0590062000
_diffrn_orient_matrix_UB_23      0.0463822000
_diffrn_orient_matrix_UB_31      0.0977863000
_diffrn_orient_matrix_UB_32      -0.0072137000
_diffrn_orient_matrix_UB_33      -0.0109776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2610
_reflns_number_total             3225
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.3131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C10(H10), C15(H15), C2(H2), C12(H12), C11(H11), C14(H14),
 C3(H3), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71798(7) 0.15074(6) 0.33623(4) 0.01367(14) Uani 1 1 d . . . . .
Cl1 Cl 0.94713(8) 0.42171(6) 0.85479(4) 0.02193(15) Uani 1 1 d . . . . .
O2 O 0.89473(19) 0.14464(17) 0.27526(13) 0.0203(3) Uani 1 1 d . . . . .
O1 O 0.6026(2) 0.01089(16) 0.33432(13) 0.0188(3) Uani 1 1 d . . . . .
O3 O 0.7700(2) 0.74837(16) 0.51860(13) 0.0209(3) Uani 1 1 d . . . . .
N1 N 0.5900(2) 0.28805(19) 0.27323(15) 0.0148(4) Uani 1 1 d . . . . .
C7 C 0.7070(3) 0.5000(2) 0.41318(18) 0.0127(4) Uani 1 1 d . . . . .
C6 C 0.7661(3) 0.3965(2) 0.50670(18) 0.0122(4) Uani 1 1 d . . . . .
C5 C 0.8268(3) 0.4517(2) 0.62422(18) 0.0139(4) Uani 1 1 d . . . . .
H5 H 0.838666 0.558514 0.643501 0.017 Uiso 1 1 calc R . . . .
C8 C 0.6219(3) 0.4425(2) 0.30698(18) 0.0141(4) Uani 1 1 d . . . . .
H8 H 0.582030 0.514800 0.252710 0.017 Uiso 1 1 calc R . . . .
C9 C 0.4878(3) 0.2410(2) 0.16053(18) 0.0144(4) Uani 1 1 d . . . . .
C10 C 0.3008(3) 0.1925(2) 0.16602(19) 0.0169(4) Uani 1 1 d . . . . .
H10 H 0.241678 0.188948 0.240575 0.020 Uiso 1 1 calc R . . . .
C15 C 0.7130(3) 0.6707(2) 0.42856(19) 0.0166(4) Uani 1 1 d . . . . .
H15 H 0.669095 0.724994 0.363311 0.020 Uiso 1 1 calc R . . . .
C1 C 0.7560(3) 0.2326(2) 0.48404(18) 0.0132(4) Uani 1 1 d . . . . .
C2 C 0.7960(3) 0.1286(2) 0.57334(18) 0.0165(4) Uani 1 1 d . . . . .
H2 H 0.784351 0.021433 0.555558 0.020 Uiso 1 1 calc R . . . .
C4 C 0.8686(3) 0.3470(2) 0.71082(18) 0.0158(4) Uani 1 1 d . . . . .
C12 C 0.2930(3) 0.1529(2) -0.05258(19) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.226876 0.123174 -0.124534 0.025 Uiso 1 1 calc R . . . .
C11 C 0.2021(3) 0.1489(2) 0.05829(19) 0.0201(5) Uani 1 1 d . . . . .
H11 H 0.075450 0.117030 0.060263 0.024 Uiso 1 1 calc R . . . .
C14 C 0.5802(3) 0.2463(3) 0.05070(19) 0.0195(5) Uani 1 1 d . . . . .
H14 H 0.706333 0.279601 0.048719 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8531(3) 0.1860(2) 0.68843(18) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.880509 0.118643 0.749404 0.020 Uiso 1 1 calc R . . . .
C13 C 0.4804(3) 0.2009(3) -0.0563(2) 0.0234(5) Uani 1 1 d . . . . .
H13 H 0.540385 0.202830 -0.130636 0.028 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 1.4331(15) . ?
S1 O1 1.4286(14) . ?
S1 N1 1.6787(17) . ?
S1 C1 1.7473(19) . ?
Cl1 C4 1.748(2) . ?
O3 C15 1.217(2) . ?
N1 C8 1.366(2) . ?
N1 C9 1.453(2) . ?
C7 C6 1.458(3) . ?
C7 C8 1.363(3) . ?
C7 C15 1.463(3) . ?
C6 C5 1.405(3) . ?
C6 C1 1.413(3) . ?
C5 C4 1.378(3) . ?
C9 C10 1.379(3) . ?
C9 C14 1.388(3) . ?
C10 C11 1.390(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.380(3) . ?
C4 C3 1.390(3) . ?
C12 C11 1.392(3) . ?
C12 C13 1.379(3) . ?
C14 C13 1.390(3) . ?

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 N1 107.72(9) . . ?
O2 S1 C1 109.25(9) . . ?
O1 S1 O2 117.79(9) . . ?
O1 S1 N1 107.42(8) . . ?
O1 S1 C1 111.92(9) . . ?
N1 S1 C1 101.34(9) . . ?
C8 N1 S1 120.51(13) . . ?
C8 N1 C9 120.73(16) . . ?
C9 N1 S1 116.41(13) . . ?
C6 C7 C15 124.30(17) . . ?
C8 C7 C6 121.25(17) . . ?
C8 C7 C15 114.12(18) . . ?
C5 C6 C7 122.83(17) . . ?
C5 C6 C1 116.51(18) . . ?
C1 C6 C7 120.60(17) . . ?
C4 C5 C6 119.85(18) . . ?
C7 C8 N1 125.77(18) . . ?
C10 C9 N1 118.76(18) . . ?
C10 C9 C14 121.83(18) . . ?
C14 C9 N1 119.41(18) . . ?
C9 C10 C11 118.91(19) . . ?
O3 C15 C7 126.21(19) . . ?
C6 C1 S1 120.65(15) . . ?
C2 C1 S1 116.20(15) . . ?
C2 C1 C6 122.77(18) . . ?
C3 C2 C1 119.46(18) . . ?
C5 C4 Cl1 117.99(15) . . ?
C5 C4 C3 123.10(19) . . ?
C3 C4 Cl1 118.90(16) . . ?
C13 C12 C11 120.34(19) . . ?
C10 C11 C12 119.9(2) . . ?
C9 C14 C13 118.7(2) . . ?
C2 C3 C4 118.26(19) . . ?
C12 C13 C14 120.3(2) . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_full_min 0.677
