# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_saurabh-27-02-second
_database_code_depnum_ccdc_archive 'CCDC 2283776'
loop_
_audit_author_name
_audit_author_address
'SAURABH KUMAR'
;BANARAS HINDU UNIVERSITY
India
;
_audit_update_record             
;
2023-07-23 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_audit_creation_date             2023-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C14 H12 Cl2 O S'
_chemical_formula_sum            'C14 H12 Cl2 O S'
_chemical_formula_weight         299.20

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration unk
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
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'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'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'

_cell_length_a                   5.7326(5)
_cell_length_b                   16.7916(19)
_cell_length_c                   14.3441(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.205(9)
_cell_angle_gamma                90
_cell_volume                     1379.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    729
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.2900
_cell_measurement_theta_min      4.0510
_exptl_absorpt_coefficient_mu    5.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4404
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_diffrn_ambient_temperature      293(2)
_exptl_crystal_F_000             621.5854
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5008
_diffrn_reflns_theta_full        72.3312
_diffrn_reflns_theta_max         72.33
_diffrn_reflns_theta_min         4.06
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9738
_diffrn_measured_fraction_theta_max 0.9738
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -39.00   1.00    1.00    --    0.00 178.00 -30.00   35
  2  ω     33.00  77.00   1.00    1.00    --    0.00-178.00 -30.00   44
  3  ω   -124.00 -79.00   1.00    1.01    --  -56.00 -99.00 -60.00   45
  4  ω    -81.00  -3.00   1.00    1.01    --  -56.00  37.00  90.00   78
  5  ω    -97.00 -26.00   1.00    1.01    --  -56.00 -77.00 -60.00   71
  6  ω   -121.00 -95.00   1.00    1.01    --  -56.00 -99.00  60.00   26
  7  ω    -75.00 -22.00   1.00    1.01    --  -56.00  57.00 -60.00   53
  8  ω     51.00  78.00   1.00    1.01    --  112.00 -25.00 120.00   27
  9  ω     85.00 112.00   1.00    1.01    --  112.00-111.00 -90.00   27
 10  ω     99.00 145.00   1.00    1.01    --  112.00 178.00  90.00   46
 11  ω     79.00 145.00   1.00    1.01    --  112.00 111.00-120.00   66
 12  ω     43.00  74.00   1.00    1.01    --  112.00 178.00  90.00   31
 13  ω     45.00 130.00   1.00    1.01    --  112.00 -50.00  60.00   85
 14  ω     47.00 106.00   1.00    1.01    --  112.00-111.00-120.00   59
 15  ω     88.00 142.00   1.00    1.01    --  112.00 -25.00 120.00   54
 16  ω     51.00 136.00   1.00    1.01    --  112.00 -37.00 -90.00   85
 17  ω    145.00 177.00   1.00    1.01    --  112.00  37.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1911715000
_diffrn_orient_matrix_UB_12      -0.0017850000
_diffrn_orient_matrix_UB_13      -0.0785463000
_diffrn_orient_matrix_UB_21      -0.0941732000
_diffrn_orient_matrix_UB_22      0.0805484000
_diffrn_orient_matrix_UB_23      0.0336263000
_diffrn_orient_matrix_UB_31      0.1642699000
_diffrn_orient_matrix_UB_32      0.0439638000
_diffrn_orient_matrix_UB_33      -0.0650558000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -5
_reflns_number_gt                1721
_reflns_number_total             2644
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.7384
_refine_diff_density_min         -0.4572
_refine_diff_density_rms         0.1162
_refine_ls_d_res_high            0.8091
_refine_ls_d_res_low             10.9018
_refine_ls_goodness_of_fit_ref   1.0169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.0169
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1162P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2285
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C9(H9), C13(H13), C12(H12), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_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
C1 C 0.3565(8) 0.3357(3) 0.2546(3) 0.0495(11) Uani 1.000000 .
C6 C 0.5276(8) 0.3277(3) 0.3259(3) 0.0492(11) Uani 1.000000 .
C5 C 0.7079(9) 0.2736(3) 0.3144(4) 0.0568(12) Uani 1.000000 .
C10 C 0.6107(10) 0.5408(4) 0.1405(4) 0.0713(16) Uani 1.000000 .
C2 C 0.3674(8) 0.2914(3) 0.1746(3) 0.0537(12) Uani 1.000000 .
C3 C 0.5459(9) 0.2378(3) 0.1637(4) 0.0557(12) Uani 1.000000 .
C8 C 0.5972(8) 0.5088(3) 0.3016(4) 0.0517(11) Uani 1.000000 .
C9 C 0.7084(9) 0.5044(3) 0.2189(4) 0.0612(13) Uani 1.000000 .
C11 C 0.3975(10) 0.5809(4) 0.1435(4) 0.0696(15) Uani 1.000000 .
C13 C 0.3849(9) 0.5492(3) 0.3074(4) 0.0606(13) Uani 1.000000 .
C12 C 0.2912(9) 0.5843(3) 0.2278(4) 0.0642(14) Uani 1.000000 .
C14 C 0.2913(13) 0.6209(5) 0.0587(5) 0.099(2) Uani 1.000000 .
C4 C 0.7182(9) 0.2293(3) 0.2337(4) 0.0589(13) Uani 1.000000 .
C7 C 0.5238(8) 0.3785(3) 0.4103(3) 0.0549(12) Uani 1.000000 .
Cl1 Cl 0.5604(3) 0.17903(9) 0.06410(10) 0.0711(5) Uani 1.000000 .
S1 S 0.7222(2) 0.46385(8) 0.40554(9) 0.0563(4) Uani 1.000000 .
Cl2 Cl 0.1548(3) 0.30497(11) 0.08679(10) 0.0807(5) Uani 1.000000 .
O1 O 0.9529(6) 0.4327(3) 0.3820(3) 0.0707(11) Uani 1.000000 .
H14a H 0.406(3) 0.625(3) 0.0118(16) 0.148(4) Uiso 1.000000 GR
H14b H 0.161(7) 0.5901(19) 0.035(2) 0.148(4) Uiso 1.000000 GR
H14c H 0.239(9) 0.6732(14) 0.0750(10) 0.148(4) Uiso 1.000000 GR
H4 H 0.8406(9) 0.1938(3) 0.2261(4) 0.0707(16) Uiso 1.000000 R
H5 H 0.8225(9) 0.2672(3) 0.3615(4) 0.0682(15) Uiso 1.000000 R
H1 H 0.2341(8) 0.3713(3) 0.2614(3) 0.0594(13) Uiso 1.000000 R
H9 H 0.8488(9) 0.4770(3) 0.2157(4) 0.0734(16) Uiso 1.000000 R
H13 H 0.3093(9) 0.5523(3) 0.3635(4) 0.0727(16) Uiso 1.000000 R
H12 H 0.1502(9) 0.6114(3) 0.2311(4) 0.0770(17) Uiso 1.000000 R
H10 H 0.6881(10) 0.5386(4) 0.0848(4) 0.0856(19) Uiso 1.000000 R
H7a H 0.3661(8) 0.3978(3) 0.4178(3) 0.0659(14) Uiso 1.000000 R
H7b H 0.5667(8) 0.3464(3) 0.4646(3) 0.0659(14) Uiso 1.000000 R


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 C6 1.396(6) . ?
C1 C2 1.371(7) . ?
C6 C5 1.391(7) . ?
C6 C7 1.481(7) . ?
C5 C4 1.379(7) . ?
C10 C9 1.379(8) . ?
C10 C11 1.398(8) . ?
C2 C3 1.376(7) . ?
C2 Cl2 1.733(5) . ?
C3 C4 1.388(7) . ?
C3 Cl1 1.741(5) . ?
C8 C9 1.369(7) . ?
C8 C13 1.398(7) . ?
C8 S1 1.796(5) . ?
C11 C12 1.376(9) . ?
C11 C14 1.497(8) . ?
C13 C12 1.375(8) . ?
C7 S1 1.833(5) . ?
S1 O1 1.473(4) . ?

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 120.6(5) . . ?
C5 C6 C1 118.6(5) . . ?
C7 C6 C1 120.8(4) . . ?
C7 C6 C5 120.5(4) . . ?
C4 C5 C6 120.6(5) . . ?
C11 C10 C9 121.1(6) . . ?
C3 C2 C1 120.5(4) . . ?
Cl2 C2 C1 118.9(4) . . ?
Cl2 C2 C3 120.6(4) . . ?
C4 C3 C2 119.8(5) . . ?
Cl1 C3 C2 121.5(4) . . ?
Cl1 C3 C4 118.6(4) . . ?
C13 C8 C9 120.9(5) . . ?
S1 C8 C9 120.8(4) . . ?
S1 C8 C13 118.3(4) . . ?
C8 C9 C10 119.6(5) . . ?
C12 C11 C10 117.7(5) . . ?
C14 C11 C10 121.3(6) . . ?
C14 C11 C12 121.0(6) . . ?
C12 C13 C8 118.1(5) . . ?
C13 C12 C11 122.6(5) . . ?
C3 C4 C5 119.9(5) . . ?
S1 C7 C6 113.0(3) . . ?
C7 S1 C8 97.6(2) . . ?
O1 S1 C8 107.0(2) . . ?
O1 S1 C7 107.2(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
;
_oxdiff_exptl_absorpt_empirical_full_max 51.440
_oxdiff_exptl_absorpt_empirical_full_min 0.545

