# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc24v1tw
_database_code_depnum_ccdc_archive 'CCDC 1991248'
loop_
_audit_author_name
_audit_author_address
'Priyankar Paira'
;IIT Madras
India
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2020-12-07 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         'C18 H11 Cl N2 S'
_chemical_formula_sum            'C18 H11 Cl N2 S'
_chemical_formula_weight         322.80

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.565(3)
_cell_length_b                   11.256(3)
_cell_length_c                   11.423(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.628(11)
_cell_angle_gamma                90
_cell_volume                     1461.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    6411
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.48
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.400
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42615
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         33.814
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5814
_reflns_number_gt                2871
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0422P)²+0.4745P] 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         5814
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.49253(15) 0.23976(16) 0.50725(15) 0.0387(4) Uani 1 1 d . . . . .
C2 C 0.40819(16) 0.17427(17) 0.55309(15) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.391951 0.190520 0.628224 0.051 Uiso 1 1 calc R U . . .
C3 C 0.35036(16) 0.08561(17) 0.48404(16) 0.0427(4) Uani 1 1 d . . . . .
C4 C 0.37340(18) 0.05770(17) 0.37133(17) 0.0469(4) Uani 1 1 d . . . . .
H4 H 0.332540 -0.003379 0.326925 0.056 Uiso 1 1 calc R U . . .
C5 C 0.45725(18) 0.12154(17) 0.32658(16) 0.0464(4) Uani 1 1 d . . . . .
H5 H 0.474027 0.103603 0.252015 0.056 Uiso 1 1 calc R U . . .
C6 C 0.51619(16) 0.21273(16) 0.39409(15) 0.0396(4) Uani 1 1 d . . . . .
C7 C 0.62287(16) 0.38021(16) 0.49740(15) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.69777(16) 0.48491(16) 0.53043(16) 0.0406(4) Uani 1 1 d . . . . .
C9 C 0.69177(17) 0.54768(18) 0.63372(17) 0.0483(5) Uani 1 1 d . . . . .
H9 H 0.640375 0.525093 0.683436 0.058 Uiso 1 1 calc R U . . .
C10 C 0.76437(18) 0.64427(19) 0.65989(19) 0.0532(5) Uani 1 1 d . . . . .
H10 H 0.762247 0.689334 0.727694 0.064 Uiso 1 1 calc R U . . .
C11 C 0.84026(18) 0.67381(18) 0.58501(19) 0.0507(5) Uani 1 1 d . . . . .
H11 H 0.889729 0.739119 0.602217 0.061 Uiso 1 1 calc R U . . .
C12 C 0.84331(16) 0.60630(16) 0.48350(16) 0.0415(4) Uani 1 1 d . . . . .
C13 C 0.92818(16) 0.62975(16) 0.40317(17) 0.0427(4) Uani 1 1 d . . . . .
C14 C 1.0031(2) 0.72775(19) 0.4184(2) 0.0591(5) Uani 1 1 d . . . . .
H14 H 0.997838 0.782617 0.478004 0.071 Uiso 1 1 calc R U . . .
C15 C 1.0853(2) 0.7445(2) 0.3459(2) 0.0653(6) Uani 1 1 d . . . . .
H15 H 1.134657 0.810358 0.357779 0.078 Uiso 1 1 calc R U . . .
C16 C 1.09509(19) 0.6659(2) 0.2575(2) 0.0583(6) Uani 1 1 d . . . . .
H16 H 1.150899 0.677359 0.209454 0.070 Uiso 1 1 calc R U . . .
C17 C 1.02078(19) 0.5693(2) 0.2406(2) 0.0593(6) Uani 1 1 d . . . . .
H17 H 1.025833 0.515601 0.179889 0.071 Uiso 1 1 calc R U . . .
C18 C 0.93881(18) 0.55145(18) 0.31280(19) 0.0514(5) Uani 1 1 d . . . . .
H18 H 0.889834 0.485346 0.300276 0.062 Uiso 1 1 calc R U . . .
N1 N 0.55428(14) 0.33503(14) 0.56405(13) 0.0433(4) Uani 1 1 d . . . . .
N2 N 0.77077(13) 0.51261(13) 0.45609(13) 0.0417(3) Uani 1 1 d . . . . .
S1 S 0.62124(4) 0.31063(4) 0.36023(4) 0.04576(14) Uani 1 1 d . . . . .
Cl1 Cl 0.24135(5) 0.00572(5) 0.53671(5) 0.06252(17) Uani 1 1 d . . . . .


_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
C1 N1 1.382(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(3) . ?
C3 Cl1 1.7435(19) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.7359(18) . ?
C7 N1 1.300(2) . ?
C7 C8 1.470(3) . ?
C7 S1 1.7487(18) . ?
C8 N2 1.340(2) . ?
C8 C9 1.388(3) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.348(2) . ?
C12 C13 1.486(3) . ?
C13 C18 1.380(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
N1 C1 C2 124.66(16) . . ?
N1 C1 C6 115.40(15) . . ?
C2 C1 C6 119.90(17) . . ?
C3 C2 C1 117.98(16) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 122.62(17) . . ?
C2 C3 Cl1 119.02(14) . . ?
C4 C3 Cl1 118.35(15) . . ?
C5 C4 C3 119.41(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.16(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.93(16) . . ?
C5 C6 S1 129.72(14) . . ?
C1 C6 S1 109.33(13) . . ?
N1 C7 C8 123.88(16) . . ?
N1 C7 S1 116.27(14) . . ?
C8 C7 S1 119.83(13) . . ?
N2 C8 C9 123.81(18) . . ?
N2 C8 C7 115.74(16) . . ?
C9 C8 C7 120.45(17) . . ?
C10 C9 C8 117.63(19) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.23(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N2 C12 C11 120.67(18) . . ?
N2 C12 C13 116.70(17) . . ?
C11 C12 C13 122.59(17) . . ?
C18 C13 C14 117.35(19) . . ?
C18 C13 C12 120.58(17) . . ?
C14 C13 C12 122.02(19) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 121.3(2) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C7 N1 C1 110.29(15) . . ?
C8 N2 C12 118.21(16) . . ?
C6 S1 C7 88.68(9) . . ?

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 177.05(17) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 Cl1 -177.90(14) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
Cl1 C3 C4 C5 178.47(15) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 S1 -177.65(15) . . . . ?
N1 C1 C6 C5 -177.99(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 S1 0.7(2) . . . . ?
C2 C1 C6 S1 178.52(14) . . . . ?
N1 C7 C8 N2 174.08(17) . . . . ?
S1 C7 C8 N2 -6.9(2) . . . . ?
N1 C7 C8 C9 -5.0(3) . . . . ?
S1 C7 C8 C9 173.92(14) . . . . ?
N2 C8 C9 C10 0.6(3) . . . . ?
C7 C8 C9 C10 179.70(17) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 N2 1.2(3) . . . . ?
C10 C11 C12 C13 -176.38(18) . . . . ?
N2 C12 C13 C18 -6.3(3) . . . . ?
C11 C12 C13 C18 171.31(18) . . . . ?
N2 C12 C13 C14 176.36(18) . . . . ?
C11 C12 C13 C14 -6.0(3) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 176.8(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C12 C13 C18 C17 -177.21(19) . . . . ?
C16 C17 C18 C13 0.5(3) . . . . ?
C8 C7 N1 C1 178.07(16) . . . . ?
S1 C7 N1 C1 -0.9(2) . . . . ?
C2 C1 N1 C7 -177.60(17) . . . . ?
C6 C1 N1 C7 0.1(2) . . . . ?
C9 C8 N2 C12 0.5(3) . . . . ?
C7 C8 N2 C12 -178.57(15) . . . . ?
C11 C12 N2 C8 -1.4(3) . . . . ?
C13 C12 N2 C8 176.27(15) . . . . ?
C5 C6 S1 C7 177.57(19) . . . . ?
C1 C6 S1 C7 -0.93(14) . . . . ?
N1 C7 S1 C6 1.12(15) . . . . ?
C8 C7 S1 C6 -177.92(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 N1 0.93 2.59 3.425(2) 150.5 4_565 yes

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052

