# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1948431'
loop_
_audit_author_name
_audit_author_address
'yongquan Ning'
;nenu
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-03-02
_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 H12 Cl N3 O2 S'
_chemical_formula_sum            'C15 H12 Cl N3 O2 S'
_chemical_formula_weight         333.79
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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'
'-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                   16.0974(10)
_cell_length_b                   11.1555(8)
_cell_length_c                   17.8712(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3209.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2993
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7090
_cell_measurement_theta_min      4.3380
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12699
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.269
_diffrn_reflns_theta_min         3.653
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             3856
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.300
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.049
_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)+(0.0555P)²+0.6733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1603
_refine_special_details          ?
_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:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00J,H00K)
;
_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
S01 S 0.36326(4) 0.33061(7) 0.53253(4) 0.0595(3) Uani 1 1 d . . . . .
Cl02 Cl 0.07626(6) 0.36442(10) 0.81860(5) 0.0979(4) Uani 1 1 d . . . . .
O003 O 0.43124(13) 0.3629(2) 0.48415(12) 0.0756(6) Uani 1 1 d . . . . .
O004 O 0.35991(13) 0.21111(17) 0.56201(13) 0.0745(6) Uani 1 1 d . . . . .
N005 N 0.42057(18) 0.5994(3) 0.66866(15) 0.0768(8) Uani 1 1 d . . . . .
C006 C 0.29261(16) 0.4155(2) 0.66329(14) 0.0485(6) Uani 1 1 d . . . . .
C007 C 0.36104(16) 0.4322(2) 0.60822(15) 0.0522(7) Uani 1 1 d . . . . .
C008 C 0.26903(18) 0.3615(3) 0.48636(14) 0.0559(7) Uani 1 1 d . . . . .
N009 N 0.4826(2) 0.6666(3) 0.66894(16) 0.0883(9) Uani 1 1 d . . . . .
C00A C 0.16069(19) 0.3839(3) 0.75919(15) 0.0596(7) Uani 1 1 d . . . . .
C00B C 0.22675(19) 0.4942(3) 0.66314(18) 0.0687(9) Uani 1 1 d . . . . .
H00B H 0.226624 0.558341 0.629902 0.082 Uiso 1 1 calc R . . . .
C00C C 0.41852(17) 0.5168(3) 0.60981(17) 0.0602(8) Uani 1 1 d . . . . .
H00C H 0.457713 0.521370 0.571686 0.072 Uiso 1 1 calc R . . . .
C00D C 0.2908(2) 0.3209(3) 0.71226(16) 0.0653(8) Uani 1 1 d . . . . .
H00D H 0.334762 0.266793 0.712826 0.078 Uiso 1 1 calc R . . . .
C00E C 0.1988(2) 0.2975(3) 0.50532(18) 0.0708(9) Uani 1 1 d . . . . .
H00E H 0.201984 0.233614 0.538646 0.085 Uiso 1 1 calc R . . . .
C00F C 0.16086(19) 0.4791(3) 0.71170(18) 0.0677(8) Uani 1 1 d . . . . .
H00F H 0.117066 0.533462 0.711912 0.081 Uiso 1 1 calc R . . . .
C00G C 0.2251(2) 0.3043(3) 0.76066(17) 0.0734(9) Uani 1 1 d . . . . .
H00G H 0.224639 0.239956 0.793747 0.088 Uiso 1 1 calc R . . . .
C00H C 0.2644(2) 0.4548(3) 0.43659(18) 0.0760(9) Uani 1 1 d . . . . .
H00H H 0.311780 0.497826 0.423822 0.091 Uiso 1 1 calc R . . . .
C00I C 0.1241(2) 0.3296(3) 0.47421(19) 0.0784(10) Uani 1 1 d . . . . .
H00I H 0.076506 0.287215 0.487320 0.094 Uiso 1 1 calc R . . . .
C00J C 0.1179(2) 0.4219(3) 0.42456(19) 0.0771(9) Uani 1 1 d . . . . .
N00K N 0.5348(3) 0.7320(4) 0.6779(2) 0.1348(16) Uani 1 1 d . . . . .
C00L C 0.1892(3) 0.4837(3) 0.4060(2) 0.0886(11) Uani 1 1 d . . . . .
H00L H 0.186054 0.546514 0.371852 0.106 Uiso 1 1 calc R . . . .
C00M C 0.0357(2) 0.4577(4) 0.3902(3) 0.1196(15) Uani 1 1 d . . . . .
H00A H -0.006468 0.401737 0.405172 0.179 Uiso 1 1 calc GR . . . .
H00J H 0.040478 0.457643 0.336697 0.179 Uiso 1 1 calc GR . . . .
H00K H 0.020798 0.536612 0.407059 0.179 Uiso 1 1 calc GR . . . .


_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
S01 O003 1.441(2) . ?
S01 O004 1.434(2) . ?
S01 C007 1.765(3) . ?
S01 C008 1.761(3) . ?
Cl02 C00A 1.738(3) . ?
N005 N009 1.249(4) . ?
N005 C00C 1.399(4) . ?
C006 C007 1.489(4) . ?
C006 C00B 1.376(4) . ?
C006 C00D 1.372(4) . ?
C007 C00C 1.321(4) . ?
C008 C00E 1.380(4) . ?
C008 C00H 1.371(4) . ?
N009 N00K 1.124(4) . ?
C00A C00F 1.359(4) . ?
C00A C00G 1.366(4) . ?
C00B C00F 1.381(4) . ?
C00D C00G 1.379(4) . ?
C00E C00I 1.372(4) . ?
C00H C00L 1.367(5) . ?
C00I C00J 1.363(4) . ?
C00J C00L 1.380(5) . ?
C00J C00M 1.512(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
O003 S01 C007 108.34(13) . . ?
O003 S01 C008 108.91(13) . . ?
O004 S01 O003 118.79(13) . . ?
O004 S01 C007 108.34(13) . . ?
O004 S01 C008 108.76(13) . . ?
C008 S01 C007 102.47(13) . . ?
N009 N005 C00C 114.7(3) . . ?
C00B C006 C007 119.3(2) . . ?
C00D C006 C007 122.3(2) . . ?
C00D C006 C00B 118.4(3) . . ?
C006 C007 S01 116.18(19) . . ?
C00C C007 S01 117.4(2) . . ?
C00C C007 C006 126.4(3) . . ?
C00E C008 S01 119.3(2) . . ?
C00H C008 S01 120.0(2) . . ?
C00H C008 C00E 120.5(3) . . ?
N00K N009 N005 171.1(4) . . ?
C00F C00A Cl02 118.7(3) . . ?
C00F C00A C00G 121.2(3) . . ?
C00G C00A Cl02 120.0(2) . . ?
C006 C00B C00F 120.8(3) . . ?
C007 C00C N005 120.2(3) . . ?
C006 C00D C00G 121.3(3) . . ?
C00I C00E C008 118.9(3) . . ?
C00A C00F C00B 119.3(3) . . ?
C00A C00G C00D 118.9(3) . . ?
C00L C00H C008 119.2(3) . . ?
C00J C00I C00E 121.7(3) . . ?
C00I C00J C00L 118.2(3) . . ?
C00I C00J C00M 121.9(3) . . ?
C00L C00J C00M 119.9(3) . . ?
C00H C00L C00J 121.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
