# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_BG51
_database_code_depnum_ccdc_archive 'CCDC 1904334'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR-Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-14 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         'C24 H21 N O2 S'
_chemical_formula_sum            'C24 H21 N O2 S'
_chemical_formula_weight         387.48

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.1000(10)
_cell_length_b                   9.6228(12)
_cell_length_c                   14.7780(18)
_cell_angle_alpha                98.898(2)
_cell_angle_beta                 99.647(2)
_cell_angle_gamma                113.901(2)
_cell_volume                     1006.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1937
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      23.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10001
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3555
_reflns_number_gt                2624
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.5283(4) 0.6753(3) 0.1422(2) 0.0366(7) Uani 1 1 d . . . . .
C2 C 0.8113(5) 0.9207(4) 0.2175(2) 0.0502(9) Uani 1 1 d . . . . .
H2 H 0.909860 1.021100 0.235999 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7861(4) 0.8137(4) 0.2696(2) 0.0479(8) Uani 1 1 d . . . . .
H3 H 0.866938 0.831649 0.327479 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6248(4) 0.6724(3) 0.2272(2) 0.0412(7) Uani 1 1 d . . . . .
H4 H 0.587409 0.586443 0.253634 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3548(4) 0.5618(3) 0.0699(2) 0.0357(7) Uani 1 1 d . . . . .
C6 C 0.2119(4) 0.4281(3) 0.08635(19) 0.0327(7) Uani 1 1 d . . . . .
C7 C 0.1864(4) 0.3732(3) 0.1773(2) 0.0352(7) Uani 1 1 d . . . . .
C8 C -0.0693(4) 0.1994(3) 0.0500(2) 0.0414(7) Uani 1 1 d . . . . .
H8A H -0.194974 0.189621 0.031513 0.050 Uiso 1 1 calc R U . . .
H8B H -0.070924 0.099347 0.025168 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0617(4) 0.3250(3) 0.0141(2) 0.0335(7) Uani 1 1 d . . . . .
C10 C -0.1334(4) 0.2039(4) -0.1487(2) 0.0480(8) Uani 1 1 d . . . . .
H10A H -0.139001 0.103271 -0.145629 0.072 Uiso 1 1 calc R U . . .
H10B H -0.121174 0.220914 -0.210105 0.072 Uiso 1 1 calc R U . . .
H10C H -0.245722 0.207194 -0.138240 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3143(4) 0.3005(3) 0.2129(2) 0.0341(7) Uani 1 1 d . . . . .
C12 C 0.4211(4) 0.2631(3) 0.1587(2) 0.0423(8) Uani 1 1 d . . . . .
H12 H 0.424263 0.289621 0.100916 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5239(5) 0.1859(4) 0.1903(3) 0.0530(9) Uani 1 1 d . . . . .
H13 H 0.595239 0.161294 0.153297 0.064 Uiso 1 1 calc R U . . .
C14 C 0.5212(5) 0.1462(4) 0.2744(3) 0.0566(9) Uani 1 1 d . . . . .
H14 H 0.589675 0.094128 0.294773 0.068 Uiso 1 1 calc R U . . .
C15 C 0.4160(5) 0.1834(4) 0.3299(3) 0.0607(10) Uani 1 1 d . . . . .
H15 H 0.414346 0.157260 0.387827 0.073 Uiso 1 1 calc R U . . .
C16 C 0.3136(5) 0.2597(4) 0.2987(2) 0.0471(8) Uani 1 1 d . . . . .
H16 H 0.242795 0.284170 0.336109 0.056 Uiso 1 1 calc R U . . .
C17 C 0.1914(4) 0.4965(3) 0.2560(2) 0.0372(7) Uani 1 1 d . . . . .
H17 H 0.303418 0.586947 0.280588 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0508(5) 0.4874(4) 0.2930(2) 0.0452(8) Uani 1 1 d . . . . .
H18 H -0.061277 0.397452 0.266708 0.054 Uiso 1 1 calc R U . . .
C19 C 0.0507(5) 0.6021(4) 0.3703(2) 0.0449(8) Uani 1 1 d . . . . .
C20 C 0.1988(5) 0.7475(4) 0.4113(2) 0.0593(10) Uani 1 1 d . . . . .
H20 H 0.305996 0.777084 0.389242 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1898(7) 0.8507(5) 0.4854(3) 0.0745(12) Uani 1 1 d . . . . .
H21 H 0.290640 0.948602 0.512496 0.089 Uiso 1 1 calc R U . . .
C22 C 0.0312(7) 0.8078(6) 0.5188(3) 0.0764(13) Uani 1 1 d . . . . .
H22 H 0.024943 0.876281 0.568454 0.092 Uiso 1 1 calc R U . . .
C23 C -0.1148(7) 0.6653(5) 0.4788(3) 0.0727(12) Uani 1 1 d . . . . .
H23 H -0.221559 0.636342 0.501229 0.087 Uiso 1 1 calc R U . . .
C24 C -0.1079(5) 0.5623(4) 0.4050(2) 0.0585(10) Uani 1 1 d . . . . .
H24 H -0.210222 0.465188 0.378182 0.070 Uiso 1 1 calc R U . . .
N1 N 0.0254(4) 0.3248(3) -0.07700(18) 0.0393(6) Uani 1 1 d . . . . .
H1N H 0.110(4) 0.406(4) -0.088(2) 0.039(9) Uiso 1 1 d . . . . .
O1 O 0.3354(3) 0.5924(2) -0.00974(14) 0.0482(6) Uani 1 1 d . . . . .
O2 O -0.0018(3) 0.2459(2) 0.14874(14) 0.0415(5) Uani 1 1 d . . . . .
S1 S 0.64369(12) 0.85169(9) 0.11491(6) 0.0472(3) 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 C4 1.375(4) . ?
C1 C5 1.484(4) . ?
C1 S1 1.723(3) . ?
C2 C3 1.351(4) . ?
C2 S1 1.688(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 O1 1.256(3) . ?
C5 C6 1.428(4) . ?
C6 C9 1.365(4) . ?
C6 C7 1.533(4) . ?
C7 O2 1.453(3) . ?
C7 C17 1.510(4) . ?
C7 C11 1.536(4) . ?
C8 O2 1.400(3) . ?
C8 C9 1.489(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.328(4) . ?
C10 N1 1.443(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.384(4) . ?
C11 C16 1.384(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.322(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.461(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 C24 1.394(5) . ?
C20 C21 1.393(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.353(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 H1N 0.87(3) . ?

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 C1 C5 134.8(3) . . ?
C4 C1 S1 110.4(2) . . ?
C5 C1 S1 114.8(2) . . ?
C3 C2 S1 112.3(2) . . ?
C3 C2 H2 123.8 . . ?
S1 C2 H2 123.8 . . ?
C2 C3 C4 112.9(3) . . ?
C2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
C1 C4 C3 112.4(3) . . ?
C1 C4 H4 123.8 . . ?
C3 C4 H4 123.8 . . ?
O1 C5 C6 119.9(3) . . ?
O1 C5 C1 115.4(3) . . ?
C6 C5 C1 124.6(3) . . ?
C9 C6 C5 120.6(3) . . ?
C9 C6 C7 108.0(2) . . ?
C5 C6 C7 131.4(3) . . ?
O2 C7 C17 107.4(2) . . ?
O2 C7 C6 103.4(2) . . ?
C17 C7 C6 113.3(2) . . ?
O2 C7 C11 105.6(2) . . ?
C17 C7 C11 111.2(2) . . ?
C6 C7 C11 115.1(2) . . ?
O2 C8 C9 105.6(2) . . ?
O2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O2 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
N1 C9 C6 129.1(3) . . ?
N1 C9 C8 120.7(3) . . ?
C6 C9 C8 110.2(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.2(3) . . ?
C12 C11 C7 122.1(3) . . ?
C16 C11 C7 119.6(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C7 125.8(3) . . ?
C18 C17 H17 117.1 . . ?
C7 C17 H17 117.1 . . ?
C17 C18 C19 127.6(3) . . ?
C17 C18 H18 116.2 . . ?
C19 C18 H18 116.2 . . ?
C20 C19 C24 117.9(3) . . ?
C20 C19 C18 123.8(3) . . ?
C24 C19 C18 118.3(3) . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.5(4) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.0(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C19 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C9 N1 C10 124.4(3) . . ?
C9 N1 H1N 111(2) . . ?
C10 N1 H1N 124(2) . . ?
C8 O2 C7 111.1(2) . . ?
C2 S1 C1 91.94(16) . . ?

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
S1 C2 C3 C4 -1.3(4) . . . . ?
C5 C1 C4 C3 179.8(3) . . . . ?
S1 C1 C4 C3 1.8(3) . . . . ?
C2 C3 C4 C1 -0.3(4) . . . . ?
C4 C1 C5 O1 -162.8(3) . . . . ?
S1 C1 C5 O1 15.2(3) . . . . ?
C4 C1 C5 C6 19.3(5) . . . . ?
S1 C1 C5 C6 -162.7(2) . . . . ?
O1 C5 C6 C9 5.9(4) . . . . ?
C1 C5 C6 C9 -176.3(2) . . . . ?
O1 C5 C6 C7 -171.9(3) . . . . ?
C1 C5 C6 C7 5.9(5) . . . . ?
C9 C6 C7 O2 -7.8(3) . . . . ?
C5 C6 C7 O2 170.3(3) . . . . ?
C9 C6 C7 C17 -123.6(3) . . . . ?
C5 C6 C7 C17 54.4(4) . . . . ?
C9 C6 C7 C11 106.9(3) . . . . ?
C5 C6 C7 C11 -75.1(4) . . . . ?
C5 C6 C9 N1 2.6(5) . . . . ?
C7 C6 C9 N1 -179.2(3) . . . . ?
C5 C6 C9 C8 -178.2(2) . . . . ?
C7 C6 C9 C8 0.1(3) . . . . ?
O2 C8 C9 N1 -172.7(2) . . . . ?
O2 C8 C9 C6 8.0(3) . . . . ?
O2 C7 C11 C12 102.8(3) . . . . ?
C17 C7 C11 C12 -141.0(3) . . . . ?
C6 C7 C11 C12 -10.5(4) . . . . ?
O2 C7 C11 C16 -72.2(3) . . . . ?
C17 C7 C11 C16 43.9(4) . . . . ?
C6 C7 C11 C16 174.4(3) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C7 C11 C12 C13 -174.9(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C12 C11 C16 C15 -0.1(5) . . . . ?
C7 C11 C16 C15 175.1(3) . . . . ?
O2 C7 C17 C18 1.4(4) . . . . ?
C6 C7 C17 C18 114.9(3) . . . . ?
C11 C7 C17 C18 -113.6(3) . . . . ?
C7 C17 C18 C19 178.6(3) . . . . ?
C17 C18 C19 C20 6.2(5) . . . . ?
C17 C18 C19 C24 -173.6(3) . . . . ?
C24 C19 C20 C21 0.3(5) . . . . ?
C18 C19 C20 C21 -179.5(3) . . . . ?
C19 C20 C21 C22 0.1(6) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
C22 C23 C24 C19 0.4(6) . . . . ?
C20 C19 C24 C23 -0.6(5) . . . . ?
C18 C19 C24 C23 179.2(3) . . . . ?
C6 C9 N1 C10 176.1(3) . . . . ?
C8 C9 N1 C10 -3.1(4) . . . . ?
C9 C8 O2 C7 -13.3(3) . . . . ?
C17 C7 O2 C8 133.2(2) . . . . ?
C6 C7 O2 C8 13.2(3) . . . . ?
C11 C7 O2 C8 -108.1(2) . . . . ?
C3 C2 S1 C1 2.0(3) . . . . ?
C4 C1 S1 C2 -2.1(2) . . . . ?
C5 C1 S1 C2 179.4(2) . . . . ?

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
N1 H1N O1 0.87(3) 1.97(3) 2.656(3) 135(3) . yes

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.058

