# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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_2A
_database_code_depnum_ccdc_archive 'CCDC 2210192'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2A                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.885 Why?
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data collection.
This leads to low theta-full value.
;
_vrf_PLAT911_2A                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 139 Report
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data collection.
This leads to low theta-full value.
;
# end Validation Reply Form
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2A
_chemical_formula_moiety         'C7 H5 N S'
_chemical_formula_sum            'C7 H5 N S'
_chemical_formula_weight         135.18
_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'
N N 0.0061 0.0033 '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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8648(6)
_cell_length_b                   4.5145(4)
_cell_length_c                   16.9480(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.830(8)
_cell_angle_gamma                90
_cell_volume                     671.94(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    140(1)
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method 'In situ cryocrystallization'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1643
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.117
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      140(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_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                1513
_reflns_number_total             1643
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0893
_refine_ls_restrained_S_all      1.243
_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)+(0.0394P)²+3.3666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2264
_refine_ls_wR_factor_ref         0.2285
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.712(6)
 0.288(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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 0.22108(17) -0.0647(4) 0.59315(8) 0.0354(4) Uani 1 1 d . . . . .
N1 N 0.2868(6) 0.2796(13) 0.4683(3) 0.0357(12) Uani 1 1 d . . . . .
C7 C 0.2539(6) 0.1384(14) 0.5206(3) 0.0267(12) Uani 1 1 d . . . . .
C1 C 0.2723(6) 0.4870(12) 0.4064(3) 0.0236(11) Uani 1 1 d . . . . .
C2 C 0.1315(6) 0.6102(14) 0.3791(3) 0.0260(11) Uani 1 1 d . . . . .
H2 H 0.044161 0.556793 0.402715 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1200(6) 0.8111(14) 0.3174(3) 0.0281(12) Uani 1 1 d . . . . .
H3 H 0.023894 0.895151 0.297767 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2487(6) 0.8913(13) 0.2836(3) 0.0267(11) Uani 1 1 d . . . . .
H4 H 0.241183 1.032036 0.241630 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3863(6) 0.7656(15) 0.3115(3) 0.0324(13) Uani 1 1 d . . . . .
H5 H 0.473496 0.819523 0.287822 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4018(6) 0.5619(15) 0.3733(3) 0.0296(12) Uani 1 1 d . . . . .
H6 H 0.497875 0.476626 0.392340 0.036 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0387(7) 0.0364(10) 0.0329(6) 0.0082(6) 0.0117(5) 0.0045(7)
N1 0.052(3) 0.028(3) 0.026(2) 0.001(2) -0.0003(19) 0.001(2)
C7 0.027(2) 0.026(4) 0.026(2) -0.004(2) -0.0003(17) 0.006(2)
C1 0.037(2) 0.010(3) 0.0226(19) -0.0025(19) 0.0014(17) -0.002(2)
C2 0.028(2) 0.021(4) 0.029(2) -0.005(2) 0.0053(17) -0.005(2)
C3 0.028(2) 0.027(4) 0.028(2) -0.002(2) -0.0013(18) 0.000(2)
C4 0.042(3) 0.017(3) 0.022(2) -0.0008(19) 0.0045(18) -0.003(2)
C5 0.035(3) 0.033(4) 0.032(2) -0.004(2) 0.016(2) -0.001(2)
C6 0.026(2) 0.029(4) 0.033(2) -0.008(2) 0.0001(18) 0.000(2)

_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 C7 1.592(6) . ?
N1 C7 1.161(7) . ?
N1 C1 1.398(7) . ?
C1 C2 1.387(7) . ?
C1 C6 1.386(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(8) . ?
C6 H6 0.9500 . ?

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
C7 N1 C1 158.9(6) . . ?
N1 C7 S1 175.8(5) . . ?
C2 C1 N1 120.3(5) . . ?
C6 C1 N1 118.0(5) . . ?
C6 C1 C2 121.6(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.7(5) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.1(5) . . . . ?
N1 C1 C6 C5 179.4(5) . . . . ?
C7 N1 C1 C2 -10.9(19) . . . . ?
C7 N1 C1 C6 169.7(15) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C4 C5 C6 C1 0.2(9) . . . . ?
C6 C1 C2 C3 0.3(8) . . . . ?

_shelx_res_file                  
;
TITL MONOP_a.res in P2(1)/c
    ncs.res
    created by SHELXL-2018/3 at 05:26:58 on 22-May-2023
CELL 0.71073 8.8648 4.5145 16.948 90 97.83 90
ZERR 4 0.0006 0.0004 0.0016 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 28 20 4 4

L.S. 20
PLAN  1
SIZE 0.3 0.3 0.3
TEMP -133.15
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\NCS.hkl">
REM </olex2.extras>

WGHT    0.039400    3.366600
BASF   0.28848
FVAR      35.06522
S1    4    0.221082   -0.064690    0.593146    11.00000    0.03872    0.03642 =
         0.03290    0.00817    0.01174    0.00445
N1    3    0.286834    0.279583    0.468275    11.00000    0.05204    0.02769 =
         0.02582    0.00137   -0.00035    0.00127
C7    1    0.253912    0.138399    0.520620    11.00000    0.02714    0.02588 =
         0.02586   -0.00389   -0.00035    0.00574
C1    1    0.272330    0.487012    0.406418    11.00000    0.03702    0.01034 =
         0.02261   -0.00251    0.00138   -0.00171
C2    1    0.131546    0.610232    0.379126    11.00000    0.02780    0.02150 =
         0.02905   -0.00524    0.00530   -0.00451
AFIX  43
H2    2    0.044161    0.556793    0.402715    11.00000   -1.20000
AFIX   0
C3    1    0.119969    0.811140    0.317370    11.00000    0.02768    0.02722 =
         0.02794   -0.00166   -0.00135   -0.00021
AFIX  43
H3    2    0.023894    0.895151    0.297767    11.00000   -1.20000
AFIX   0
C4    1    0.248711    0.891266    0.283648    11.00000    0.04154    0.01683 =
         0.02186   -0.00081    0.00449   -0.00255
AFIX  43
H4    2    0.241183    1.032036    0.241630    11.00000   -1.20000
AFIX   0
C5    1    0.386281    0.765642    0.311500    11.00000    0.03499    0.03328 =
         0.03212   -0.00429    0.01559   -0.00125
AFIX  43
H5    2    0.473496    0.819523    0.287822    11.00000   -1.20000
AFIX   0
C6    1    0.401814    0.561913    0.373324    11.00000    0.02553    0.02880 =
         0.03345   -0.00778    0.00006    0.00046
AFIX  43
H6    2    0.497875    0.476626    0.392340    11.00000   -1.20000
AFIX   0
HKLF 5




REM  MONOP_a.res in P2(1)/c
REM wR2 = 0.2285, GooF = S = 1.243, Restrained GooF = 1.243 for all data
REM R1 = 0.0893 for 1513 Fo > 4sig(Fo) and 0.0940 for all 1643 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0398      3.3617

REM Highest difference peak  0.468,  deepest hole -0.505,  1-sigma level  0.118
Q1    1   0.1379 -0.2839  0.5319  11.00000  0.05    0.47
;
_shelx_res_checksum              40490
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.712(6)
2 0.288(6)

####################################################################### 
# 
# 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_1B
_database_code_depnum_ccdc_archive 'CCDC 2210193'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1B                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.924 Why?
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data
collection.This leads to low theta-full value.
;
# end Validation Reply Form
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1B
_chemical_formula_moiety         'C5 H4 O S'
_chemical_formula_sum            'C5 H4 O S'
_chemical_formula_weight         112.14
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2300(4)
_cell_length_b                   7.9881(4)
_cell_length_c                   8.7762(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.799(3)
_cell_angle_gamma                90
_cell_volume                     506.61(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2275
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.7420.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method 'Insitu cryo crystalization'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6554
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.123
_diffrn_reflns_theta_min         3.450
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1127
_reflns_number_total             1306
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.060
_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)+(0.0535P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.81699(5) 0.54213(6) 0.66390(5) 0.02724(16) Uani 1 1 d . . . . .
O1 O 0.23264(16) 0.84830(18) 0.59556(14) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.5034(2) 0.6829(2) 0.62757(16) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.6266(2) 0.7745(2) 0.53457(17) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.5885(2) 0.5536(2) 0.70414(18) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.8005(2) 0.7112(2) 0.54264(18) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.3083(2) 0.7232(2) 0.64664(18) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.528(3) 0.471(3) 0.777(2) 0.026(5) Uiso 1 1 d . . . . .
H3 H 0.596(3) 0.863(3) 0.477(2) 0.031(5) Uiso 1 1 d . . . . .
H5 H 0.240(3) 0.637(3) 0.707(2) 0.029(5) Uiso 1 1 d . . . . .
H4 H 0.910(3) 0.752(3) 0.495(3) 0.035(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0224(2) 0.0285(3) 0.0308(2) 0.00307(16) 0.00120(15) 0.00434(15)
O1 0.0229(5) 0.0304(8) 0.0403(7) -0.0009(5) 0.0064(5) 0.0039(5)
C2 0.0195(6) 0.0197(9) 0.0197(7) -0.0032(5) 0.0038(5) -0.0022(5)
C3 0.0217(7) 0.0220(10) 0.0217(7) 0.0012(6) 0.0046(5) -0.0005(6)
C1 0.0242(7) 0.0224(10) 0.0241(7) 0.0001(6) 0.0043(6) -0.0017(6)
C4 0.0209(7) 0.0264(10) 0.0255(7) 0.0003(6) 0.0044(5) -0.0016(6)
C5 0.0207(7) 0.0273(11) 0.0255(8) -0.0046(6) 0.0060(6) -0.0018(6)

_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 C1 1.7023(16) . ?
S1 C4 1.7212(18) . ?
O1 C5 1.218(2) . ?
C2 C3 1.428(2) . ?
C2 C1 1.368(2) . ?
C2 C5 1.462(2) . ?
C3 C4 1.355(2) . ?
C3 H3 0.89(2) . ?
C1 H1 1.03(2) . ?
C4 H4 0.97(2) . ?
C5 H5 1.01(2) . ?

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
C1 S1 C4 92.13(8) . . ?
C3 C2 C5 125.02(15) . . ?
C1 C2 C3 112.87(14) . . ?
C1 C2 C5 122.07(14) . . ?
C2 C3 H3 125.4(14) . . ?
C4 C3 C2 111.89(15) . . ?
C4 C3 H3 122.7(14) . . ?
S1 C1 H1 122.2(12) . . ?
C2 C1 S1 111.31(12) . . ?
C2 C1 H1 126.5(12) . . ?
S1 C4 H4 119.6(14) . . ?
C3 C4 S1 111.80(12) . . ?
C3 C4 H4 128.5(14) . . ?
O1 C5 C2 124.21(15) . . ?
O1 C5 H5 122.0(12) . . ?
C2 C5 H5 113.7(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 S1 -0.62(19) . . . . ?
C3 C2 C1 S1 -0.10(18) . . . . ?
C3 C2 C5 O1 -6.7(3) . . . . ?
C1 S1 C4 C3 0.49(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C5 O1 170.79(15) . . . . ?
C4 S1 C1 C2 -0.21(13) . . . . ?
C5 C2 C3 C4 178.13(15) . . . . ?
C5 C2 C1 S1 -177.83(12) . . . . ?

_shelx_res_file                  
;
TITL MONO1_a.res in P2(1)/n
    3cht.res
    created by SHELXL-2018/3 at 05:22:28 on 22-May-2023
REM Old TITL MONO1 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.082, Rweak 0.003, Alpha 0.018, Orientation as input
REM Formula found by SHELXT: C5 O S
CELL 0.71073 7.23 7.9881 8.7762 90 91.799 90
ZERR 4 0.0004 0.0004 0.0005 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H O S
UNIT 20 16 4 4

L.S. 7
PLAN  5
SIZE 0.3 0.3 0.3
TEMP -173.15
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\3CHT.hkl">
REM </olex2.extras>

WGHT    0.053500    0.202600
FVAR       1.19655
S1    4    0.816992    0.542131    0.663904    11.00000    0.02243    0.02846 =
         0.03085    0.00307    0.00120    0.00434
O1    3    0.232645    0.848297    0.595556    11.00000    0.02291    0.03040 =
         0.04031   -0.00086    0.00645    0.00394
C2    1    0.503406    0.682905    0.627571    11.00000    0.01948    0.01972 =
         0.01967   -0.00318    0.00375   -0.00224
C3    1    0.626562    0.774544    0.534567    11.00000    0.02168    0.02205 =
         0.02169    0.00120    0.00459   -0.00053
C1    1    0.588548    0.553622    0.704140    11.00000    0.02416    0.02238 =
         0.02411    0.00006    0.00426   -0.00171
C4    1    0.800509    0.711179    0.542636    11.00000    0.02092    0.02642 =
         0.02548    0.00031    0.00441   -0.00160
C5    1    0.308293    0.723178    0.646644    11.00000    0.02069    0.02735 =
         0.02553   -0.00461    0.00604   -0.00179
H1    2    0.527562    0.471151    0.776805    11.00000    0.02588
H3    2    0.595729    0.863399    0.477245    11.00000    0.03104
H5    2    0.239941    0.637483    0.707353    11.00000    0.02939
H4    2    0.909943    0.752194    0.494626    11.00000    0.03509
HKLF 4




REM  MONO1_a.res in P2(1)/n
REM wR2 = 0.0983, GooF = S = 1.060, Restrained GooF = 1.060 for all data
REM R1 = 0.0375 for 1127 Fo > 4sig(Fo) and 0.0449 for all 1306 data
REM 80 parameters refined using 0 restraints

END

WGHT      0.0535      0.2026

REM Highest difference peak  0.591,  deepest hole -0.260,  1-sigma level  0.063
Q1    1   0.8190  0.6258  0.5967  11.00000  0.05    0.59
Q2    1   0.5571  0.7327  0.5801  11.00000  0.05    0.41
Q3    1   0.8241  0.6010  0.7372  11.00000  0.05    0.40
Q4    1   0.4132  0.7043  0.6348  11.00000  0.05    0.36
Q5    1   0.7062  0.7261  0.5222  11.00000  0.05    0.32
;
_shelx_res_checksum              21512
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1A
_database_code_depnum_ccdc_archive 'CCDC 2210195'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1A                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.873 Why?
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data
collection.This leads to low theta-full value.
;
_vrf_PLAT911_1A                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 50 Report
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data
collection.This leads to lowtheta-full value.
;
# end Validation Reply Form
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1A
_chemical_formula_moiety         'C5 H4 O S'
_chemical_formula_sum            'C5 H4 O S'
_chemical_formula_weight         112.14
_chemical_absolute_configuration ?
_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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.52550(10)
_cell_length_b                   5.90890(10)
_cell_length_c                   16.0342(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     523.511(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0711 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method 'Insitu cryocrystallization'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.873
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7298
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.686
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                949
_reflns_number_total             966
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0886
_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:
 C2(H2), C5(H5), C3(H3), C4(H4)
;
_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 0.48707(17) 0.61387(11) 0.55730(4) 0.0509(3) Uani 1 1 d . . . . .
O1 O 0.0632(5) 0.8144(4) 0.65414(14) 0.0628(8) Uani 1 1 d . . . . .
C2 C 0.4254(6) 0.3004(4) 0.66702(17) 0.0447(8) Uani 1 1 d . . . . .
H2 H 0.362955 0.213867 0.712074 0.054 Uiso 1 1 calc R U . . .
C5 C 0.1317(7) 0.6304(5) 0.67704(17) 0.0497(8) Uani 1 1 d . . . . .
H5 H 0.047236 0.561036 0.721869 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3330(6) 0.5081(4) 0.64110(15) 0.0366(6) Uani 1 1 d . . . . .
C3 C 0.6249(7) 0.2360(5) 0.6170(2) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.713900 0.100203 0.625162 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6759(6) 0.3886(5) 0.5562(2) 0.0522(8) Uani 1 1 d . . . . .
H4 H 0.803920 0.370751 0.517250 0.063 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0543(6) 0.0416(4) 0.0566(4) 0.0091(3) 0.0106(4) 0.0014(4)
O1 0.065(2) 0.0604(13) 0.0628(12) -0.0109(10) -0.0075(12) 0.0246(12)
C2 0.050(2) 0.0365(12) 0.0476(13) 0.0009(11) -0.0073(12) 0.0018(11)
C5 0.049(2) 0.0586(17) 0.0416(12) -0.0044(13) -0.0010(13) 0.0035(15)
C1 0.0383(19) 0.0348(12) 0.0367(11) -0.0005(9) -0.0038(11) -0.0018(11)
C3 0.053(2) 0.0355(13) 0.0668(17) -0.0064(13) -0.0196(16) 0.0096(13)
C4 0.038(2) 0.0499(16) 0.0684(18) -0.0119(16) 0.0050(15) 0.0039(12)

_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 C1 1.709(3) . ?
S1 C4 1.691(3) . ?
O1 C5 1.209(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.393(4) . ?
C2 C3 1.416(5) . ?
C5 H5 0.9500 . ?
C5 C1 1.446(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(5) . ?
C4 H4 0.9500 . ?

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
C4 S1 C1 91.57(15) . . ?
C1 C2 H2 124.7 . . ?
C1 C2 C3 110.7(3) . . ?
C3 C2 H2 124.7 . . ?
O1 C5 H5 117.7 . . ?
O1 C5 C1 124.7(3) . . ?
C1 C5 H5 117.7 . . ?
C2 C1 S1 112.0(2) . . ?
C2 C1 C5 127.1(3) . . ?
C5 C1 S1 120.9(2) . . ?
C2 C3 H3 123.5 . . ?
C4 C3 C2 112.9(3) . . ?
C4 C3 H3 123.5 . . ?
S1 C4 H4 123.6 . . ?
C3 C4 S1 112.8(3) . . ?
C3 C4 H4 123.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C1 S1 -2.9(5) . . . . ?
O1 C5 C1 C2 177.3(3) . . . . ?
C2 C3 C4 S1 0.2(4) . . . . ?
C1 S1 C4 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C3 C2 C1 S1 0.9(3) . . . . ?
C3 C2 C1 C5 -179.3(3) . . . . ?
C4 S1 C1 C2 -0.7(2) . . . . ?
C4 S1 C1 C5 179.5(3) . . . . ?

_shelx_res_file                  
;
TITL ORTHO1_a.res in P2(1)2(1)2(1)
    2cht.res
    created by SHELXL-2018/3 at 05:20:51 on 22-May-2023
REM Old TITL ORTHO1 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.119, Rweak 0.041, Alpha 0.001, Orientation as input
REM Flack x = 0.079 ( 0.031 ) from Parsons' quotients
REM Formula found by SHELXT: C5 O S
CELL 0.71073 5.5255 5.9089 16.0342 90 90 90
ZERR 4 0.0001 0.0001 0.0004 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H O S
UNIT 20 16 4 4

L.S. 10
PLAN  1
TEMP -173.15
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\2CHT.hkl">
REM </olex2.extras>

WGHT    0.051300    0.116000
FVAR       1.85101
S1    4    0.487068    0.613871    0.557298    11.00000    0.05431    0.04163 =
         0.05664    0.00907    0.01056    0.00140
O1    3    0.063225    0.814433    0.654137    11.00000    0.06518    0.06041 =
         0.06284   -0.01086   -0.00746    0.02456
C2    1    0.425355    0.300440    0.667017    11.00000    0.05015    0.03647 =
         0.04760    0.00093   -0.00731    0.00179
AFIX  43
H2    2    0.362955    0.213867    0.712074    11.00000   -1.20000
AFIX   0
C5    1    0.131719    0.630375    0.677038    11.00000    0.04904    0.05857 =
         0.04159   -0.00441   -0.00103    0.00355
AFIX  43
H5    2    0.047236    0.561036    0.721869    11.00000   -1.20000
AFIX   0
C1    1    0.333027    0.508131    0.641096    11.00000    0.03829    0.03484 =
         0.03671   -0.00054   -0.00377   -0.00176
C3    1    0.624942    0.235999    0.617022    11.00000    0.05284    0.03546 =
         0.06675   -0.00638   -0.01958    0.00961
AFIX  43
H3    2    0.713900    0.100203    0.625162    11.00000   -1.20000
AFIX   0
C4    1    0.675872    0.388584    0.556238    11.00000    0.03826    0.04994 =
         0.06842   -0.01192    0.00500    0.00392
AFIX  43
H4    2    0.803920    0.370751    0.517250    11.00000   -1.20000
AFIX   0
HKLF 4




REM  ORTHO1_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0886, GooF = S = 1.112, Restrained GooF = 1.112 for all data
REM R1 = 0.0311 for 949 Fo > 4sig(Fo) and 0.0315 for all 966 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0513      0.1160

REM Highest difference peak  0.185,  deepest hole -0.258,  1-sigma level  0.039
Q1    1   0.5829  0.4974  0.5619  11.00000  0.05    0.19
;
_shelx_res_checksum              11763
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2B
_database_code_depnum_ccdc_archive 'CCDC 2210194'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2B                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.945 Why?
RESPONSE: Due to instrumentation constraint for experimental setup of in
situ cryocrystallization of liquids, only omega-scan is employed for data collection.
This leads to low theta-full value.
;
_vrf_PLAT911_2B                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 82 Report
RESPONSE: Due to instrumentation constraint for experimental setup of in
situcryocrystallization of liquids, only omega-scan is employed for data collection.
This leads to low theta-full value.
;
# end Validation Reply Form
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2B
_chemical_formula_moiety         'C8 H4 F3 N S'
_chemical_formula_sum            'C8 H4 F3 N S'
_chemical_formula_weight         203.18
_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'
F F 0.0171 0.0103 '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'
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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2687(4)
_cell_length_b                   7.8122(2)
_cell_length_c                   8.0302(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.369(2)
_cell_angle_gamma                90
_cell_volume                     832.15(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4676
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method 'In situ cryocrytsallization'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13286
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.065
_diffrn_reflns_theta_min         3.026
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_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                1762
_reflns_number_total             2169
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.3268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0837
_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:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_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 0.54541(3) 0.73284(6) 0.68858(5) 0.04139(14) Uani 1 1 d . . . . .
F1 F 0.94024(7) 0.56506(12) 0.33479(12) 0.0445(3) Uani 1 1 d . . . . .
F2 F 0.86874(8) 0.64142(11) 0.55996(11) 0.0409(2) Uani 1 1 d . . . . .
F3 F 0.78680(8) 0.65244(11) 0.32664(11) 0.0424(3) Uani 1 1 d . . . . .
N1 N 0.66589(11) 0.48229(19) 0.56367(17) 0.0406(3) Uani 1 1 d . . . . .
C1 C 0.72477(10) 0.34735(19) 0.51249(16) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.81771(10) 0.37842(17) 0.44007(15) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.87627(11) 0.24124(18) 0.39223(17) 0.0266(3) Uani 1 1 d . . . . .
H3 H 0.939748 0.261131 0.343482 0.032 Uiso 1 1 calc R U . . .
C4 C 0.84296(11) 0.07531(19) 0.41494(17) 0.0299(3) Uani 1 1 d . . . . .
H4 H 0.883742 -0.018323 0.382502 0.036 Uiso 1 1 calc R U . . .
C5 C 0.75036(11) 0.0456(2) 0.48482(18) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.727426 -0.068569 0.499037 0.038 Uiso 1 1 calc R U . . .
C6 C 0.69113(11) 0.1804(2) 0.53398(18) 0.0308(3) Uani 1 1 d . . . . .
H6 H 0.627641 0.159471 0.582290 0.037 Uiso 1 1 calc R U . . .
C7 C 0.85289(12) 0.55731(19) 0.41486(17) 0.0316(3) Uani 1 1 d . . . . .
C8 C 0.61381(10) 0.58682(19) 0.61745(16) 0.0257(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0375(2) 0.0452(3) 0.0417(2) -0.00999(18) 0.00615(17) 0.01362(18)
F1 0.0513(6) 0.0326(5) 0.0502(6) 0.0038(4) 0.0138(5) -0.0122(4)
F2 0.0630(6) 0.0249(5) 0.0345(5) -0.0070(4) -0.0066(4) -0.0059(4)
F3 0.0644(6) 0.0232(5) 0.0392(5) 0.0050(4) -0.0092(5) 0.0042(4)
N1 0.0400(7) 0.0453(9) 0.0366(7) -0.0063(6) 0.0007(6) 0.0158(6)
C1 0.0286(7) 0.0296(8) 0.0223(6) -0.0019(5) -0.0007(5) 0.0066(6)
C2 0.0311(7) 0.0210(7) 0.0194(6) -0.0010(5) -0.0013(5) 0.0005(5)
C3 0.0291(7) 0.0255(8) 0.0253(7) -0.0029(5) 0.0040(5) 0.0001(5)
C4 0.0365(8) 0.0233(8) 0.0300(7) -0.0036(5) 0.0013(6) 0.0044(6)
C5 0.0393(8) 0.0246(8) 0.0300(7) 0.0035(5) -0.0029(6) -0.0065(6)
C6 0.0268(7) 0.0378(9) 0.0278(7) 0.0039(6) 0.0013(5) -0.0040(6)
C7 0.0425(8) 0.0245(8) 0.0276(7) -0.0007(5) -0.0010(6) -0.0015(6)
C8 0.0216(6) 0.0319(8) 0.0236(6) -0.0004(5) 0.0018(5) -0.0026(5)

_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 C8 1.5735(15) . ?
F1 C7 1.3402(18) . ?
F2 C7 1.3498(16) . ?
F3 C7 1.3392(17) . ?
N1 C1 1.3805(19) . ?
N1 C8 1.1598(19) . ?
C1 C2 1.3973(19) . ?
C1 C6 1.390(2) . ?
C2 C3 1.3836(19) . ?
C2 C7 1.489(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9500 . ?

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
C8 N1 C1 174.24(17) . . ?
N1 C1 C2 120.18(14) . . ?
N1 C1 C6 119.58(13) . . ?
C6 C1 C2 120.25(13) . . ?
C1 C2 C7 120.16(13) . . ?
C3 C2 C1 119.22(13) . . ?
C3 C2 C7 120.63(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.40(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.06(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.43(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.64(13) . . ?
C5 C6 H6 120.2 . . ?
F1 C7 F2 105.87(12) . . ?
F1 C7 C2 112.65(12) . . ?
F2 C7 C2 112.49(12) . . ?
F3 C7 F1 106.49(12) . . ?
F3 C7 F2 105.85(12) . . ?
F3 C7 C2 112.92(12) . . ?
N1 C8 S1 178.29(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.92(13) . . . . ?
N1 C1 C2 C7 -1.12(19) . . . . ?
N1 C1 C6 C5 -179.21(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C7 F1 -176.09(12) . . . . ?
C1 C2 C7 F2 64.34(17) . . . . ?
C1 C2 C7 F3 -55.40(17) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C2 C7 F1 3.86(18) . . . . ?
C3 C2 C7 F2 -115.71(14) . . . . ?
C3 C2 C7 F3 124.56(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -0.87(19) . . . . ?
C6 C1 C2 C7 179.08(13) . . . . ?
C7 C2 C3 C4 -179.59(13) . . . . ?

_shelx_res_file                  
;
TITL MONO1_a.res in P2(1)/c
    2cfncs.res
    created by SHELXL-2018/3 at 06:04:42 on 22-May-2023
CELL 0.71073 13.2687 7.8122 8.0302 90 91.369 90
ZERR 4 0.0004 0.0002 0.0002 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N S
UNIT 32 16 12 4 4

L.S. 10
PLAN  5
SIZE 0.3 0.3 0.3
TEMP -133
CONF
HTAB
BOND $H
LIST 4
MORE -1
fmap 2
acta
OMIT 1 0 0
REM <olex2.extras>
REM <HklSrc "%.\\2CFNCS.hkl">
REM </olex2.extras>

WGHT    0.033300    0.326800
FVAR       1.08200
S1    5    0.545412    0.732844    0.688585    11.00000    0.03751    0.04517 =
         0.04174   -0.00999    0.00615    0.01362
F1    3    0.940236    0.565064    0.334789    11.00000    0.05132    0.03265 =
         0.05020    0.00384    0.01382   -0.01217
F2    3    0.868741    0.641417    0.559964    11.00000    0.06295    0.02489 =
         0.03447   -0.00698   -0.00655   -0.00587
F3    3    0.786803    0.652444    0.326637    11.00000    0.06442    0.02322 =
         0.03921    0.00504   -0.00920    0.00424
N1    4    0.665886    0.482291    0.563671    11.00000    0.03999    0.04527 =
         0.03660   -0.00630    0.00071    0.01576
C1    1    0.724766    0.347351    0.512493    11.00000    0.02859    0.02958 =
         0.02227   -0.00188   -0.00074    0.00661
C2    1    0.817711    0.378421    0.440067    11.00000    0.03114    0.02096 =
         0.01935   -0.00099   -0.00126    0.00046
C3    1    0.876272    0.241235    0.392228    11.00000    0.02908    0.02546 =
         0.02529   -0.00290    0.00398    0.00006
AFIX  43
H3    2    0.939748    0.261131    0.343482    11.00000   -1.20000
AFIX   0
C4    1    0.842958    0.075309    0.414945    11.00000    0.03648    0.02328 =
         0.02999   -0.00359    0.00126    0.00441
AFIX  43
H4    2    0.883742   -0.018323    0.382502    11.00000   -1.20000
AFIX   0
C5    1    0.750359    0.045580    0.484823    11.00000    0.03933    0.02457 =
         0.02998    0.00351   -0.00294   -0.00654
AFIX  43
H5    2    0.727426   -0.068569    0.499037    11.00000   -1.20000
AFIX   0
C6    1    0.691126    0.180426    0.533978    11.00000    0.02682    0.03777 =
         0.02782    0.00386    0.00130   -0.00401
AFIX  43
H6    2    0.627641    0.159471    0.582290    11.00000   -1.20000
AFIX   0
C7    1    0.852887    0.557314    0.414865    11.00000    0.04249    0.02454 =
         0.02759   -0.00065   -0.00103   -0.00146
C8    1    0.613810    0.586823    0.617448    11.00000    0.02161    0.03193 =
         0.02357   -0.00037    0.00175   -0.00257
HKLF 4




REM  MONO1_a.res in P2(1)/c
REM wR2 = 0.0837, GooF = S = 1.033, Restrained GooF = 1.033 for all data
REM R1 = 0.0337 for 1762 Fo > 4sig(Fo) and 0.0448 for all 2169 data
REM 118 parameters refined using 0 restraints

END

WGHT      0.0333      0.3268

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.246,  deepest hole -0.255,  1-sigma level  0.044
Q1    1   0.7794  0.3607  0.4849  11.00000  0.05    0.25
Q2    1   0.8409  0.3161  0.4086  11.00000  0.05    0.24
Q3    1   0.8362  0.4545  0.4324  11.00000  0.05    0.23
Q4    1   0.7002  0.2586  0.5043  11.00000  0.05    0.23
Q5    1   0.7997  0.0691  0.4584  11.00000  0.05    0.23
;
_shelx_res_checksum              65338
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1C
_database_code_depnum_ccdc_archive 'CCDC 2210196'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_1C                  
;
PROBLEM: Short Inter HL..A Contact Br1 ..O1 . 3.02 Ang.
RESPONSE: The mentioned interaction is a halogen bond interaction for
which the distance criteria of less than the sum of the 
van der Waals radii is well
documented in the literature.
;
# end Validation Reply Form
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1C
_chemical_formula_moiety         'C5 H3 Br O S'
_chemical_formula_sum            'C5 H3 Br O S'
_chemical_formula_weight         191.04
_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'
Br Br -0.2901 2.4595 '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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.1013(2)
_cell_length_b                   8.5014(3)
_cell_length_c                   17.1726(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.856(2)
_cell_angle_gamma                90
_cell_volume                     598.69(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      3.37
_shelx_estimated_absorpt_T_max   0.607
_shelx_estimated_absorpt_T_min   0.125
_exptl_absorpt_coefficient_mu    7.098
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_correction_T_min  0.1661
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0559 before and 0.0352 after correction.
The Ratio of minimum to maximum transmission is 0.2213.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method 'Slow evaporation from cyclohexane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6373
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.566
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1472
_reflns_number_total             1674
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+0.4825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0489
_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:
 C2(H2), C5(H5), C4(H4)
;
_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
Br1 Br 0.93800(5) 0.38181(2) 0.61332(2) 0.01359(7) Uani 1 1 d . . . . .
S1 S 0.60630(13) 0.83337(6) 0.70571(3) 0.01330(12) Uani 1 1 d . . . . .
O1 O 0.1949(4) 1.05054(19) 0.59861(9) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.7655(5) 0.5820(2) 0.63485(11) 0.0114(4) Uani 1 1 d . . . . .
C2 C 0.5880(5) 0.6711(2) 0.57931(11) 0.0121(4) Uani 1 1 d . . . . .
H2 H 0.546211 0.638316 0.527220 0.015 Uiso 1 1 calc R U . . .
C5 C 0.2842(5) 0.9280(3) 0.57006(12) 0.0144(4) Uani 1 1 d . . . . .
H5 H 0.219383 0.907003 0.517755 0.017 Uiso 1 1 calc R U . . .
C1 C 0.4836(5) 0.8106(3) 0.60991(10) 0.0114(4) Uani 1 1 d . . . . .
C4 C 0.7958(5) 0.6548(2) 0.70561(11) 0.0128(4) Uani 1 1 d . . . . .
H4 H 0.908435 0.611254 0.749291 0.015 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01607(12) 0.01082(11) 0.01382(10) -0.00152(8) -0.00122(7) 0.00345(9)
S1 0.0165(3) 0.0114(3) 0.0119(2) -0.00185(19) -0.00055(19) 0.0010(2)
O1 0.0237(9) 0.0148(8) 0.0234(8) 0.0002(7) -0.0008(7) 0.0063(7)
C3 0.0106(10) 0.0100(10) 0.0137(9) 0.0003(8) 0.0015(7) -0.0003(8)
C2 0.0120(10) 0.0126(10) 0.0117(9) 0.0007(8) 0.0007(7) -0.0031(8)
C5 0.0140(11) 0.0149(10) 0.0143(9) 0.0039(8) 0.0010(8) 0.0001(9)
C1 0.0116(11) 0.0126(10) 0.0102(9) 0.0000(7) 0.0006(7) -0.0016(8)
C4 0.0122(11) 0.0114(10) 0.0148(9) 0.0001(8) -0.0009(8) 0.0002(8)

_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
Br1 C3 1.882(2) . ?
S1 C1 1.7241(19) . ?
S1 C4 1.706(2) . ?
O1 C5 1.210(3) . ?
C3 C2 1.412(3) . ?
C3 C4 1.367(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.368(3) . ?
C5 H5 0.9500 . ?
C5 C1 1.455(3) . ?
C4 H4 0.9500 . ?

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
C4 S1 C1 91.47(10) . . ?
C2 C3 Br1 122.95(15) . . ?
C4 C3 Br1 123.64(15) . . ?
C4 C3 C2 113.40(18) . . ?
C3 C2 H2 124.3 . . ?
C1 C2 C3 111.50(17) . . ?
C1 C2 H2 124.3 . . ?
O1 C5 H5 117.6 . . ?
O1 C5 C1 124.85(19) . . ?
C1 C5 H5 117.6 . . ?
C2 C1 S1 112.04(15) . . ?
C2 C1 C5 126.22(18) . . ?
C5 C1 S1 121.72(16) . . ?
S1 C4 H4 124.2 . . ?
C3 C4 S1 111.59(15) . . ?
C3 C4 H4 124.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C2 C1 178.68(15) . . . . ?
Br1 C3 C4 S1 -179.06(11) . . . . ?
O1 C5 C1 S1 1.8(3) . . . . ?
O1 C5 C1 C2 179.9(2) . . . . ?
C3 C2 C1 S1 0.7(2) . . . . ?
C3 C2 C1 C5 -177.5(2) . . . . ?
C2 C3 C4 S1 0.2(2) . . . . ?
C1 S1 C4 C3 0.15(18) . . . . ?
C4 S1 C1 C2 -0.51(17) . . . . ?
C4 S1 C1 C5 177.83(18) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?

_shelx_res_file                  
;
TITL MONOF_a.res in P2(1)/c
    4b2cht.res
    created by SHELXL-2018/3 at 05:25:08 on 22-May-2023
REM Old TITL MONOF in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.049, Rweak 0.003, Alpha 0.022, Orientation as input
REM Formula found by SHELXT: C5 Br O S
CELL 0.71073 4.1013 8.5014 17.1726 90 90.856 90
ZERR 4 0.0002 0.0003 0.0006 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br O S
UNIT 20 12 4 4 4

L.S. 10
PLAN  1
SIZE 0.078 0.284 0.5
TEMP -173.15
CONF
LIST 4
MORE -1
BOND $H
fmap 2
acta
OMIT -3 7 10
REM <olex2.extras>
REM <HklSrc "%.\\4B2CHT.hkl">
REM </olex2.extras>

WGHT    0.017800    0.482500
FVAR       0.61698
BR1   3    0.937999    0.381812    0.613324    11.00000    0.01607    0.01082 =
         0.01382   -0.00152   -0.00122    0.00345
S1    5    0.606300    0.833366    0.705708    11.00000    0.01655    0.01143 =
         0.01189   -0.00185   -0.00055    0.00104
O1    4    0.194914    1.050543    0.598615    11.00000    0.02370    0.01478 =
         0.02337    0.00020   -0.00079    0.00632
C3    1    0.765478    0.582042    0.634853    11.00000    0.01056    0.00995 =
         0.01372    0.00035    0.00153   -0.00029
C2    1    0.587959    0.671099    0.579307    11.00000    0.01198    0.01263 =
         0.01174    0.00075    0.00071   -0.00312
AFIX  43
H2    2    0.546211    0.638316    0.527220    11.00000   -1.20000
AFIX   0
C5    1    0.284229    0.928039    0.570065    11.00000    0.01404    0.01493 =
         0.01429    0.00392    0.00100    0.00008
AFIX  43
H5    2    0.219383    0.907003    0.517755    11.00000   -1.20000
AFIX   0
C1    1    0.483550    0.810590    0.609911    11.00000    0.01159    0.01256 =
         0.01021    0.00002    0.00063   -0.00156
C4    1    0.795810    0.654780    0.705614    11.00000    0.01224    0.01136 =
         0.01475    0.00011   -0.00093    0.00018
AFIX  43
H4    2    0.908435    0.611254    0.749291    11.00000   -1.20000
AFIX   0
HKLF 4




REM  MONOF_a.res in P2(1)/c
REM wR2 = 0.0489, GooF = S = 1.068, Restrained GooF = 1.068 for all data
REM R1 = 0.0235 for 1472 Fo > 4sig(Fo) and 0.0295 for all 1674 data
REM 73 parameters refined using 0 restraints

END

WGHT      0.0178      0.4825

REM Highest difference peak  0.474,  deepest hole -0.382,  1-sigma level  0.106
Q1    1   0.9870  0.4278  0.5593  11.00000  0.05    0.47
;
_shelx_res_checksum              17081
_olex2_submission_special_instructions 'No special instructions were received'
