# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_PPALPH4Cl_a
_database_code_depnum_ccdc_archive 'CCDC 2263865'
loop_
_audit_author_name
_audit_author_address
'Pritishree Panigrahi'
;IIT Guwahati
India
;
_audit_update_record             
;
2023-05-18 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl N O2 S'
_chemical_formula_weight         318.78

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'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.756(8)
_cell_length_b                   8.641(5)
_cell_length_c                   14.081(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.558(14)
_cell_angle_gamma                90
_cell_volume                     1534.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8628
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.80

_exptl_crystal_description       niddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33602
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2688
_reflns_number_gt                2425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.7860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.67502(4) 0.64726(5) 0.64161(3) 0.03855(17) Uani 1 1 d . . . . .
Cl02 Cl 0.43712(5) 0.35631(14) 0.09752(6) 0.1131(4) Uani 1 1 d . . . . .
O003 O 0.57986(12) 0.56564(18) 0.63015(12) 0.0547(4) Uani 1 1 d . . . . .
O004 O 0.73863(13) 0.71432(19) 0.74058(11) 0.0584(4) Uani 1 1 d . . . . .
C005 C 0.70889(15) 0.4630(2) 0.50030(14) 0.0381(4) Uani 1 1 d . . . . .
H005 H 0.638405 0.431379 0.473249 0.046 Uiso 1 1 calc R U . . .
C006 C 0.71866(14) 0.4075(2) 0.33156(14) 0.0386(4) Uani 1 1 d . . . . .
C007 C 0.76188(14) 0.4582(2) 0.44006(14) 0.0397(4) Uani 1 1 d . . . . .
H007 H 0.832430 0.489518 0.468823 0.048 Uiso 1 1 calc R U . . .
C008 C 0.63897(14) 0.7932(2) 0.54610(14) 0.0382(4) Uani 1 1 d . . . . .
C009 C 0.75766(15) 0.5173(2) 0.61000(14) 0.0410(4) Uani 1 1 d . . . . .
H00A H 0.824400 0.568233 0.622012 0.049 Uiso 1 1 calc R U . . .
H00B H 0.772891 0.428320 0.655658 0.049 Uiso 1 1 calc R U . . .
C00A C 0.78641(15) 0.3625(2) 0.28360(15) 0.0420(4) Uani 1 1 d . . . . .
C00B C 0.54719(16) 0.7758(3) 0.45749(15) 0.0475(5) Uani 1 1 d . . . . .
H00C H 0.506489 0.686460 0.446986 0.057 Uiso 1 1 calc R U . . .
C00C C 0.70044(16) 0.9248(2) 0.56258(18) 0.0513(5) Uani 1 1 d . . . . .
H00D H 0.762018 0.935546 0.622367 0.062 Uiso 1 1 calc R U . . .
C00D C 0.61017(15) 0.4046(3) 0.27153(15) 0.0499(5) Uani 1 1 d . . . . .
H00E H 0.562880 0.434618 0.300284 0.060 Uiso 1 1 calc R U . . .
C00E C 0.74593(16) 0.3155(3) 0.18048(16) 0.0510(5) Uani 1 1 d . . . . .
H00F H 0.792095 0.285530 0.150383 0.061 Uiso 1 1 calc R U . . .
N00F N 0.98942(16) 0.3684(3) 0.38224(17) 0.0827(8) Uani 1 1 d . . . . .
C00G C 0.89966(17) 0.3653(3) 0.34004(16) 0.0536(6) Uani 1 1 d . . . . .
C00H C 0.63901(18) 0.3129(3) 0.12307(17) 0.0582(6) Uani 1 1 d . . . . .
H00H H 0.611760 0.281762 0.054110 0.070 Uiso 1 1 calc R U . . .
C00I C 0.6687(2) 1.0399(3) 0.4887(2) 0.0677(7) Uani 1 1 d . . . . .
H00I H 0.709451 1.129010 0.498314 0.081 Uiso 1 1 calc R U . . .
C00J C 0.57248(17) 0.3575(3) 0.16978(18) 0.0584(6) Uani 1 1 d . . . . .
C00K C 0.51696(19) 0.8932(3) 0.38488(18) 0.0614(6) Uani 1 1 d . . . . .
H00K H 0.455361 0.883448 0.324998 0.074 Uiso 1 1 calc R U . . .
C00L C 0.5776(2) 1.0237(3) 0.4010(2) 0.0690(7) Uani 1 1 d . . . . .
H00L H 0.556687 1.102556 0.351961 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.4381(16) . ?
S001 O004 1.4383(16) . ?
S001 C008 1.764(2) . ?
S001 C009 1.776(2) . ?
Cl02 C00J 1.729(2) . ?
C005 C007 1.322(3) . ?
C005 C009 1.493(3) . ?
C006 C00D 1.391(3) . ?
C006 C00A 1.407(3) . ?
C006 C007 1.467(3) . ?
C008 C00C 1.380(3) . ?
C008 C00B 1.383(3) . ?
C00A C00E 1.392(3) . ?
C00A C00G 1.439(3) . ?
C00B C00K 1.381(3) . ?
C00C C00I 1.379(3) . ?
C00D C00J 1.376(3) . ?
C00E C00H 1.366(3) . ?
N00F C00G 1.137(3) . ?
C00H C00J 1.378(3) . ?
C00I C00L 1.370(4) . ?
C00K C00L 1.366(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
O003 S001 O004 118.70(10) . . ?
O003 S001 C008 107.40(9) . . ?
O004 S001 C008 109.12(10) . . ?
O003 S001 C009 107.87(10) . . ?
O004 S001 C009 107.16(10) . . ?
C008 S001 C009 105.89(9) . . ?
C007 C005 C009 122.63(18) . . ?
C00D C006 C00A 117.34(18) . . ?
C00D C006 C007 121.87(16) . . ?
C00A C006 C007 120.78(17) . . ?
C005 C007 C006 125.43(18) . . ?
C00C C008 C00B 121.20(19) . . ?
C00C C008 S001 119.60(15) . . ?
C00B C008 S001 119.15(15) . . ?
C005 C009 S001 112.95(13) . . ?
C00E C00A C006 121.06(18) . . ?
C00E C00A C00G 118.32(18) . . ?
C006 C00A C00G 120.61(18) . . ?
C008 C00B C00K 118.9(2) . . ?
C00I C00C C008 118.7(2) . . ?
C00J C00D C006 120.29(18) . . ?
C00H C00E C00A 120.61(19) . . ?
N00F C00G C00A 178.2(2) . . ?
C00E C00H C00J 118.4(2) . . ?
C00L C00I C00C 120.4(2) . . ?
C00D C00J C00H 122.3(2) . . ?
C00D C00J Cl02 118.93(17) . . ?
C00H C00J Cl02 118.80(18) . . ?
C00L C00K C00B 120.0(2) . . ?
C00K C00L C00I 120.8(2) . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.038



