# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_wzh_1
_database_code_depnum_ccdc_archive 'CCDC 2291789'
loop_
_audit_author_name
_audit_author_address
'Zhiying Li'
;Jinan University
China
;
_audit_update_record             
;
2023-08-30 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 Cl0 N O S0.17'
_chemical_formula_weight         177.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   9.2120(2)
_cell_length_b                   15.9904(3)
_cell_length_c                   9.5944(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.886(3)
_cell_angle_gamma                90
_cell_volume                     1282.06(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             562
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11169
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.082
_diffrn_reflns_theta_max         73.931
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5026
_reflns_number_gt                4806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.0652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 2147 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5026
_refine_ls_number_parameters     354
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.019
_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_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
S001 S -0.40623(7) -0.46669(3) -0.73774(7) 0.02088(14) Uani 1 1 d . . . . .
O002 O -1.0000(2) -0.43977(14) -1.2150(2) 0.0330(5) Uani 1 1 d . . . . .
O003 O -1.1707(2) -0.40236(14) -1.1039(2) 0.0309(4) Uani 1 1 d . . . . .
O004 O -0.4743(2) -0.40076(11) -0.8465(2) 0.0278(4) Uani 1 1 d . . . . .
O005 O -0.2860(2) -0.44750(12) -0.5894(2) 0.0293(5) Uani 1 1 d . . . . .
O006 O -0.4041(2) -0.58220(13) -0.4963(2) 0.0272(4) Uani 1 1 d . . . . .
O007 O -0.3947(3) -0.22221(13) -0.1840(3) 0.0357(5) Uani 1 1 d . . . . .
N008 N -0.5637(3) -0.51079(13) -0.7149(2) 0.0196(4) Uani 1 1 d . . . . .
C009 C -0.9261(3) -0.45276(16) -1.0591(3) 0.0234(5) Uani 1 1 d . . . . .
C00A C -0.5913(3) -0.35306(16) -0.5186(3) 0.0226(5) Uani 1 1 d . . . . .
H00A H -0.594815 -0.356518 -0.616768 0.027 Uiso 1 1 calc R U . . .
C00B C -1.0283(3) -0.43048(17) -0.9931(3) 0.0228(5) Uani 1 1 d . . . . .
C00C C -0.8279(3) -0.46496(17) -0.7471(3) 0.0202(5) Uani 1 1 d . . . . .
C00D C -0.5354(3) -0.55568(15) -0.5790(3) 0.0203(5) Uani 1 1 d . . . . .
C00E C -0.5015(3) -0.29067(16) -0.4205(3) 0.0259(6) Uani 1 1 d . . . . .
H00E H -0.447041 -0.252448 -0.453979 0.031 Uiso 1 1 calc R U . . .
C00F C -0.7782(3) -0.65138(17) -0.3787(3) 0.0243(5) Uani 1 1 d . . . . .
C00G C -0.6767(3) -0.41097(15) -0.4737(3) 0.0200(5) Uani 1 1 d . . . . .
C00H C -0.3332(3) -0.54461(16) -0.8204(3) 0.0223(5) Uani 1 1 d . . . . .
C00I C -0.6388(3) -0.60683(16) -0.3892(3) 0.0234(5) Uani 1 1 d . . . . .
H00B H -0.552252 -0.646386 -0.368045 0.028 Uiso 1 1 calc R U . . .
H00C H -0.600802 -0.563587 -0.311102 0.028 Uiso 1 1 calc R U . . .
C00J C -0.6821(3) -0.56694(16) -0.5473(3) 0.0203(5) Uani 1 1 d . . . . .
H00J H -0.752366 -0.606504 -0.624069 0.024 Uiso 1 1 calc R U . . .
C00K C -0.3564(3) -0.53663(18) -0.9724(3) 0.0252(5) Uani 1 1 d . . . . .
H00K H -0.416471 -0.492702 -1.032679 0.030 Uiso 1 1 calc R U . . .
C00L C -0.4917(3) -0.28434(16) -0.2722(3) 0.0252(5) Uani 1 1 d . . . . .
C00M C -0.8898(4) -0.60922(16) -0.3426(3) 0.0266(6) Uani 1 1 d . . . . .
H00M H -0.877439 -0.552126 -0.322639 0.032 Uiso 1 1 calc R U . . .
C00N C -0.9838(3) -0.43708(16) -0.8382(3) 0.0223(5) Uani 1 1 d . . . . .
H00N H -1.054239 -0.423595 -0.795066 0.027 Uiso 1 1 calc R U . . .
C00O C -0.6712(4) -0.40059(17) -0.3265(3) 0.0255(6) Uani 1 1 d . . . . .
H00O H -0.731795 -0.436136 -0.295267 0.031 Uiso 1 1 calc R U . . .
C00P C -0.7250(3) -0.48498(15) -0.8143(3) 0.0206(5) Uani 1 1 d . . . . .
C00Q C -0.7741(3) -0.48173(16) -0.9746(3) 0.0234(5) Uani 1 1 d . . . . .
H00Q H -0.707460 -0.498234 -1.020258 0.028 Uiso 1 1 calc R U . . .
C00R C -1.0191(3) -0.65016(19) -0.3358(3) 0.0290(6) Uani 1 1 d . . . . .
H00R H -1.090688 -0.620961 -0.308731 0.035 Uiso 1 1 calc R U . . .
C00S C -0.2443(4) -0.6097(2) -0.7295(4) 0.0346(7) Uani 1 1 d . . . . .
H00S H -0.229198 -0.614048 -0.627655 0.042 Uiso 1 1 calc R U . . .
C00T C -0.7735(3) -0.48209(15) -0.5772(3) 0.0201(5) Uani 1 1 d . . . . .
H00T H -0.869212 -0.490405 -0.558406 0.024 Uiso 1 1 calc R U . . .
C00U C -0.5787(4) -0.33910(17) -0.2252(3) 0.0277(6) Uani 1 1 d . . . . .
H00U H -0.575368 -0.334894 -0.127247 0.033 Uiso 1 1 calc R U . . .
C00V C -0.8010(4) -0.73700(17) -0.4087(4) 0.0305(6) Uani 1 1 d . . . . .
H00V H -0.726372 -0.766822 -0.430617 0.037 Uiso 1 1 calc R U . . .
C00W C -0.2878(4) -0.59587(19) -1.0324(4) 0.0319(6) Uani 1 1 d . . . . .
H00W H -0.301837 -0.591008 -1.133918 0.038 Uiso 1 1 calc R U . . .
C00X C -0.9324(4) -0.77868(18) -0.4068(4) 0.0340(7) Uani 1 1 d . . . . .
H00X H -0.947247 -0.835360 -0.430273 0.041 Uiso 1 1 calc R U . . .
C00Y C -1.0415(4) -0.73492(19) -0.3694(4) 0.0326(6) Uani 1 1 d . . . . .
H00Y H -1.129397 -0.762370 -0.366879 0.039 Uiso 1 1 calc R U . . .
C00Z C -1.1602(4) -0.4145(2) -1.2474(3) 0.0361(7) Uani 1 1 d . . . . .
H00D H -1.235277 -0.457300 -1.307179 0.043 Uiso 1 1 calc R U . . .
H00F H -1.185958 -0.363001 -1.306183 0.043 Uiso 1 1 calc R U . . .
C010 C -0.1985(4) -0.6623(2) -0.9438(4) 0.0392(7) Uani 1 1 d . . . . .
C011 C -0.3630(5) -0.2214(2) -0.0250(4) 0.0426(8) Uani 1 1 d . . . . .
H01A H -0.460110 -0.209764 -0.014538 0.064 Uiso 1 1 calc R U . . .
H01B H -0.285234 -0.178932 0.026843 0.064 Uiso 1 1 calc R U . . .
H01C H -0.322204 -0.274940 0.019482 0.064 Uiso 1 1 calc R U . . .
C012 C -0.1780(5) -0.6681(2) -0.7919(4) 0.0451(9) Uani 1 1 d . . . . .
H012 H -0.118622 -0.712121 -0.731244 0.054 Uiso 1 1 calc R U . . .
C013 C -0.1267(7) -0.7268(3) -1.0104(6) 0.0723(15) Uani 1 1 d . . . . .
H01D H -0.201830 -0.740242 -1.113111 0.109 Uiso 1 1 calc R U . . .
H01E H -0.101991 -0.776353 -0.948217 0.109 Uiso 1 1 calc R U . . .
H01F H -0.030564 -0.704961 -1.012470 0.109 Uiso 1 1 calc R U . . .


_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
S001 O005 1.421(2) . ?
S001 O004 1.429(2) . ?
S001 N008 1.708(2) . ?
S001 C00H 1.756(3) . ?
O002 C009 1.374(3) . ?
O002 C00Z 1.432(4) . ?
O003 C00B 1.371(3) . ?
O003 C00Z 1.434(4) . ?
O006 C00D 1.210(3) . ?
O007 C00L 1.366(3) . ?
O007 C011 1.427(4) . ?
N008 C00D 1.414(3) . ?
N008 C00P 1.447(3) . ?
C009 C00Q 1.370(4) . ?
C009 C00B 1.384(4) . ?
C00A C00E 1.382(4) . ?
C00A C00G 1.396(4) . ?
C00B C00N 1.369(4) . ?
C00C C00P 1.390(3) . ?
C00C C00N 1.404(4) . ?
C00C C00T 1.515(3) . ?
C00D C00J 1.515(4) . ?
C00E C00L 1.390(4) . ?
C00F C00M 1.390(4) . ?
C00F C00V 1.397(4) . ?
C00F C00I 1.508(4) . ?
C00G C00O 1.402(4) . ?
C00G C00T 1.526(3) . ?
C00H C00S 1.383(4) . ?
C00H C00K 1.388(4) . ?
C00I C00J 1.536(4) . ?
C00J C00T 1.559(3) . ?
C00K C00W 1.391(4) . ?
C00L C00U 1.384(4) . ?
C00M C00R 1.384(4) . ?
C00O C00U 1.393(4) . ?
C00P C00Q 1.410(4) . ?
C00R C00Y 1.388(4) . ?
C00S C012 1.383(5) . ?
C00V C00X 1.389(4) . ?
C00W C010 1.392(5) . ?
C00X C00Y 1.390(4) . ?
C010 C012 1.392(5) . ?
C010 C013 1.505(5) . ?

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
O005 S001 O004 119.31(12) . . ?
O005 S001 N008 107.86(11) . . ?
O004 S001 N008 105.26(11) . . ?
O005 S001 C00H 108.69(12) . . ?
O004 S001 C00H 109.10(12) . . ?
N008 S001 C00H 105.80(11) . . ?
C009 O002 C00Z 105.8(2) . . ?
C00B O003 C00Z 105.7(2) . . ?
C00L O007 C011 117.1(2) . . ?
C00D N008 C00P 119.5(2) . . ?
C00D N008 S001 119.42(18) . . ?
C00P N008 S001 119.33(16) . . ?
C00Q C009 O002 127.6(2) . . ?
C00Q C009 C00B 122.6(2) . . ?
O002 C009 C00B 109.8(2) . . ?
C00E C00A C00G 121.4(2) . . ?
C00N C00B O003 128.2(2) . . ?
C00N C00B C009 121.8(2) . . ?
O003 C00B C009 110.0(2) . . ?
C00P C00C C00N 120.2(2) . . ?
C00P C00C C00T 118.4(2) . . ?
C00N C00C C00T 121.1(2) . . ?
O006 C00D N008 121.9(2) . . ?
O006 C00D C00J 123.8(2) . . ?
N008 C00D C00J 114.3(2) . . ?
C00A C00E C00L 120.8(2) . . ?
C00M C00F C00V 117.7(3) . . ?
C00M C00F C00I 121.8(2) . . ?
C00V C00F C00I 120.5(2) . . ?
C00A C00G C00O 116.5(2) . . ?
C00A C00G C00T 123.0(2) . . ?
C00O C00G C00T 120.4(2) . . ?
C00S C00H C00K 121.3(3) . . ?
C00S C00H S001 119.2(2) . . ?
C00K C00H S001 119.4(2) . . ?
C00F C00I C00J 112.8(2) . . ?
C00D C00J C00I 111.4(2) . . ?
C00D C00J C00T 108.6(2) . . ?
C00I C00J C00T 116.0(2) . . ?
C00H C00K C00W 118.5(3) . . ?
O007 C00L C00U 125.1(3) . . ?
O007 C00L C00E 115.5(2) . . ?
C00U C00L C00E 119.3(2) . . ?
C00R C00M C00F 121.6(3) . . ?
C00B C00N C00C 117.5(2) . . ?
C00U C00O C00G 122.6(3) . . ?
C00C C00P C00Q 121.9(2) . . ?
C00C C00P N008 118.2(2) . . ?
C00Q C00P N008 119.9(2) . . ?
C009 C00Q C00P 115.9(2) . . ?
C00M C00R C00Y 119.9(3) . . ?
C012 C00S C00H 119.2(3) . . ?
C00C C00T C00G 113.8(2) . . ?
C00C C00T C00J 105.3(2) . . ?
C00G C00T C00J 114.0(2) . . ?
C00L C00U C00O 119.2(3) . . ?
C00X C00V C00F 121.6(3) . . ?
C00K C00W C010 121.4(3) . . ?
C00V C00X C00Y 119.4(3) . . ?
C00R C00Y C00X 119.9(3) . . ?
O002 C00Z O003 108.0(2) . . ?
C012 C010 C00W 118.4(3) . . ?
C012 C010 C013 120.5(3) . . ?
C00W C010 C013 121.0(3) . . ?
C00S C012 C010 121.2(3) . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.044



