# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BSNe
_database_code_depnum_ccdc_archive 'CCDC 1872169'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 O3 S, C12 H14 N'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4468(3)
_cell_length_b                   9.8135(6)
_cell_length_c                   15.2598(10)
_cell_angle_alpha                103.033(2)
_cell_angle_beta                 93.291(2)
_cell_angle_gamma                97.938(3)
_cell_volume                     783.72(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3680
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1269 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.5640. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9206
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.217
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      116.63
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.971
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             3762
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0682
_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)+(0.0499P)²+1.9228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4), C16(H16), C3(H3), C10(H10), C15(H15), C5(H5),
 C13(H13), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.49048(14) 0.59248(9) 0.38696(5) 0.0181(2) Uani 1 1 d . . . . .
O1 O 0.2229(4) 0.5791(3) 0.39609(15) 0.0227(5) Uani 1 1 d . . . . .
O2 O 0.6289(4) 0.7185(3) 0.44836(15) 0.0246(5) Uani 1 1 d . . . . .
O3 O 0.5893(5) 0.4648(3) 0.39031(16) 0.0270(6) Uani 1 1 d . . . . .
N1 N 1.0175(5) 0.6758(3) 0.56300(18) 0.0204(6) Uani 1 1 d . . . . .
H1A H 0.874179 0.690154 0.535222 0.031 Uiso 1 1 calc GR . . . .
H1B H 0.980705 0.614958 0.599074 0.031 Uiso 1 1 calc GR . . . .
H1C H 1.115863 0.638384 0.520579 0.031 Uiso 1 1 calc GR . . . .
C1 C 0.5226(5) 0.6190(3) 0.2767(2) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.7412(6) 0.6948(4) 0.2587(2) 0.0226(7) Uani 1 1 d . . . . .
H6 H 0.873527 0.731939 0.304921 0.027 Uiso 1 1 calc R . . . .
C2 C 0.3305(6) 0.5632(4) 0.2095(2) 0.0215(7) Uani 1 1 d . . . . .
H2 H 0.181419 0.511647 0.222289 0.026 Uiso 1 1 calc R . . . .
C18 C 0.8733(6) 0.8809(4) 0.8497(2) 0.0245(7) Uani 1 1 d . . . . .
C17 C 1.0190(6) 0.8265(4) 0.7783(2) 0.0233(7) Uani 1 1 d . . . . .
C4 C 0.5718(7) 0.6594(4) 0.1047(2) 0.0268(8) Uani 1 1 d . . . . .
H4 H 0.587941 0.673557 0.045598 0.032 Uiso 1 1 calc R . . . .
C16 C 1.1835(6) 0.7321(4) 0.7949(3) 0.0264(8) Uani 1 1 d . . . . .
H16 H 1.281285 0.693028 0.748802 0.032 Uiso 1 1 calc R . . . .
C9 C 0.9996(6) 0.8703(4) 0.6959(2) 0.0232(7) Uani 1 1 d . . . . .
C8 C 1.1525(7) 0.8146(4) 0.6194(2) 0.0255(8) Uani 1 1 d . . . . .
H8 H 1.312089 0.796185 0.646898 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3578(6) 0.5832(4) 0.1235(2) 0.0260(8) Uani 1 1 d . . . . .
H3 H 0.227296 0.543929 0.076836 0.031 Uiso 1 1 calc R . . . .
C10 C 0.8365(6) 0.9618(4) 0.6854(2) 0.0268(8) Uani 1 1 d . . . . .
H10 H 0.821660 0.990378 0.630067 0.032 Uiso 1 1 calc R . . . .
C15 C 1.2012(7) 0.6979(4) 0.8761(2) 0.0299(8) Uani 1 1 d . . . . .
H15 H 1.313157 0.635818 0.886226 0.036 Uiso 1 1 calc R . . . .
C5 C 0.7637(6) 0.7154(4) 0.1723(2) 0.0278(8) Uani 1 1 d . . . . .
H5 H 0.911320 0.768190 0.159422 0.033 Uiso 1 1 calc R . . . .
C13 C 0.8943(7) 0.8410(4) 0.9315(3) 0.0323(9) Uani 1 1 d . . . . .
H13 H 0.794154 0.875842 0.977917 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6918(7) 1.0137(4) 0.7548(3) 0.0307(8) Uani 1 1 d . . . . .
H11 H 0.581422 1.077264 0.745708 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7059(7) 0.9754(4) 0.8344(3) 0.0304(8) Uani 1 1 d . . . . .
H12 H 0.604703 1.011056 0.880205 0.037 Uiso 1 1 calc R . . . .
C7 C 1.2172(7) 0.9115(4) 0.5579(3) 0.0307(8) Uani 1 1 d . . . . .
H7A H 1.341053 0.874946 0.518521 0.046 Uiso 1 1 calc GR . . . .
H7B H 1.285807 1.006343 0.594151 0.046 Uiso 1 1 calc GR . . . .
H7C H 1.067033 0.916346 0.520880 0.046 Uiso 1 1 calc GR . . . .
C14 C 1.0568(7) 0.7526(4) 0.9458(3) 0.0342(9) Uani 1 1 d . . . . .
H14 H 1.072827 0.727950 1.002377 0.041 Uiso 1 1 calc R . . . .


_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 O1 1.463(2) . ?
S1 O2 1.454(3) . ?
S1 O3 1.440(3) . ?
S1 C1 1.774(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C8 1.502(5) . ?
C1 C6 1.390(4) . ?
C1 C2 1.382(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C18 C17 1.434(5) . ?
C18 C13 1.393(5) . ?
C18 C12 1.433(5) . ?
C17 C16 1.426(5) . ?
C17 C9 1.419(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.376(5) . ?
C4 C5 1.386(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.356(5) . ?
C9 C8 1.519(4) . ?
C9 C10 1.375(5) . ?
C8 H8 1.0000 . ?
C8 C7 1.502(5) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.403(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.412(5) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.363(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.351(5) . ?
C12 H12 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C14 H14 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
O1 S1 C1 104.93(14) . . ?
O2 S1 O1 112.30(14) . . ?
O2 S1 C1 105.78(15) . . ?
O3 S1 O1 112.73(15) . . ?
O3 S1 O2 113.58(15) . . ?
O3 S1 C1 106.70(14) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
C6 C1 S1 119.6(2) . . ?
C2 C1 S1 119.6(2) . . ?
C2 C1 C6 120.8(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 C12 121.4(3) . . ?
C12 C18 C17 118.4(3) . . ?
C16 C17 C18 117.5(3) . . ?
C9 C17 C18 119.7(3) . . ?
C9 C17 C16 122.8(3) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C9 C8 120.7(3) . . ?
C10 C9 C17 119.2(3) . . ?
C10 C9 C8 120.1(3) . . ?
N1 C8 C9 109.6(3) . . ?
N1 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C7 C8 N1 108.3(3) . . ?
C7 C8 C9 115.7(3) . . ?
C7 C8 H8 107.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.5(4) . . ?
C14 C15 H15 119.3 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C18 C13 H13 119.6 . . ?
C14 C13 C18 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C18 C12 H12 120.0 . . ?
C11 C12 C18 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?

_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_BSBA
_database_code_depnum_ccdc_archive 'CCDC 1872174'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 O3 S, C7 H10 N, 0.5(H2 O)'
_chemical_formula_sum            'C13 H16 N O3.50 S'
_chemical_formula_weight         274.33
_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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.768(8)
_cell_length_b                   5.5762(12)
_cell_length_c                   15.750(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.619(3)
_cell_angle_gamma                90
_cell_volume                     2644.0(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3604
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.29
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1010 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.9211. 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    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.485
_diffrn_reflns_theta_min         1.353
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1532
_reflns_number_total             2713
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.113
_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)+(0.0889P)²+1.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C8-C13A
 1.3 with sigma of 0.02
3. Others
 Fixed Sof: O1B(0.48215) O3A(0.51785) O2B(0.48215) C13A(0.48215) H13A(0.48215)
 C12A(0.48215) H12A(0.48215) C11A(0.48215) H11A(0.48215) C10A(0.48215)
 H10A(0.48215) C9A(0.48215) H9A(0.48215) C4B(0.48215) H4B(0.48215) C6B(0.48215)
 H6B(0.48215) C5B(0.48215) H5B(0.48215) C2B(0.48215) H2B(0.48215) C3B(0.48215)
 H3B(0.48215) C6A(0.51785) H6A(0.51785) C5A(0.51785) H5A(0.51785) C4A(0.51785)
 H4A(0.51785) C3A(0.51785) H3A(0.51785) C2A(0.51785) H2A(0.51785) H4C(0.5)
 H4D(0.5) C13B(0.51785) H13B(0.51785) C9B(0.51785) H9B(0.51785) C12B(0.51785)
 H12B(0.51785) C11B(0.51785) H11B(0.51785) C10B(0.51785) H10B(0.51785)
 O2A(0.51785) O1A(0.51785) O3B(0.48215)
4.a Free rotating group:
 O4(H4C,H4D)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C13A(H13A), C12A(H12A), C11A(H11A), C10A(H10A), C9A(H9A), C4B(H4B), C6B(H6B),
 C5B(H5B), C2B(H2B), C3B(H3B), C6A(H6A), C5A(H5A), C4A(H4A), C3A(H3A), C2A(H2A),
  C13B(H13B), C9B(H9B), C12B(H12B), C11B(H11B), C10B(H10B)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.43819(2) 1.00232(15) 0.52512(5) 0.0401(3) Uani 1 1 d . . . . .
O1B O 0.4613(7) 0.879(3) 0.6086(12) 0.047(3) Uani 0.4821 1 d . . . A 2
O3A O 0.4420(6) 0.870(4) 0.4519(13) 0.080(6) Uani 0.5178 1 d . . . A 1
O2B O 0.4492(7) 1.252(3) 0.5286(10) 0.057(4) Uani 0.4821 1 d . . . A 2
N1 N 0.46796(9) 1.4547(5) 0.37747(19) 0.0579(8) Uani 1 1 d . . . . .
H1A H 0.467295 1.614239 0.377572 0.069 Uiso 1 1 calc GR . . . .
H1B H 0.495624 1.405098 0.385806 0.069 Uiso 1 1 calc GR . . . .
H1C H 0.458688 1.399000 0.421399 0.069 Uiso 1 1 calc GR . . . .
C13A C 0.3820(3) 1.6729(13) 0.2251(5) 0.062(2) Uani 0.4821 1 d D . . B 1
H13A H 0.404369 1.757801 0.212046 0.074 Uiso 0.4821 1 calc R . . B 1
C12A C 0.3404(4) 1.7606(17) 0.2028(6) 0.081(3) Uani 0.4821 1 d . . . B 1
H12A H 0.333400 1.901667 0.169746 0.098 Uiso 0.4821 1 calc R . . B 1
C11A C 0.3091(5) 1.647(3) 0.2275(9) 0.102(6) Uani 0.4821 1 d . . . B 1
H11A H 0.280508 1.709751 0.212359 0.123 Uiso 0.4821 1 calc R . . B 1
C10A C 0.3198(5) 1.430(4) 0.2772(9) 0.086(5) Uani 0.4821 1 d . . . B 1
H10A H 0.298877 1.349583 0.296557 0.104 Uiso 0.4821 1 calc R . . B 1
C9A C 0.3631(4) 1.3431(16) 0.2959(5) 0.066(2) Uani 0.4821 1 d . . . B 1
H9A H 0.370323 1.203747 0.329874 0.079 Uiso 0.4821 1 calc R . . B 1
C1 C 0.38139(11) 1.0004(8) 0.5106(2) 0.0548(9) Uani 1 1 d . . . . .
C8 C 0.39144(14) 1.4308(9) 0.2722(2) 0.0684(12) Uani 1 1 d D . . . .
C4B C 0.2922(3) 1.124(2) 0.4887(7) 0.065(3) Uani 0.4821 1 d . . . C 1
H4B H 0.262303 1.153077 0.480233 0.077 Uiso 0.4821 1 calc R . . C 1
C6B C 0.3672(2) 1.2422(12) 0.5482(5) 0.0462(17) Uani 0.4821 1 d . . . C 1
H6B H 0.388241 1.356383 0.577064 0.055 Uiso 0.4821 1 calc R . . C 1
C5B C 0.3231(3) 1.2762(14) 0.5364(5) 0.058(2) Uani 0.4821 1 d . . . C 1
H5B H 0.314393 1.409009 0.562448 0.069 Uiso 0.4821 1 calc R . . C 1
C2B C 0.3494(2) 0.8817(12) 0.4625(5) 0.0473(17) Uani 0.4821 1 d . . . C 1
H2B H 0.356324 0.754788 0.431036 0.057 Uiso 0.4821 1 calc R . . C 1
C3B C 0.3053(4) 0.917(3) 0.4508(8) 0.059(3) Uani 0.4821 1 d . . . C 1
H3B H 0.284274 0.806603 0.418567 0.071 Uiso 0.4821 1 calc R . . C 1
C7 C 0.43892(13) 1.3656(9) 0.2916(3) 0.0790(13) Uani 1 1 d . . . . .
H7A H 0.441364 1.192321 0.290815 0.095 Uiso 1 1 calc R . . . .
H7B H 0.449161 1.428656 0.244241 0.095 Uiso 1 1 calc R . . . .
C6A C 0.3511(2) 1.1250(12) 0.4633(4) 0.0455(16) Uani 0.5178 1 d . . . C 2
H6A H 0.358602 1.256877 0.434986 0.055 Uiso 0.5178 1 calc R . . C 2
C5A C 0.3061(3) 1.082(2) 0.4493(6) 0.048(2) Uani 0.5178 1 d . . . C 2
H5A H 0.285206 1.191744 0.416743 0.058 Uiso 0.5178 1 calc R . . C 2
C4A C 0.2924(3) 0.886(2) 0.4816(7) 0.054(3) Uani 0.5178 1 d . . . C 2
H4A H 0.262354 0.861949 0.472827 0.065 Uiso 0.5178 1 calc R . . C 2
C3A C 0.3238(2) 0.7166(12) 0.5289(5) 0.0552(18) Uani 0.5178 1 d . . . C 2
H3A H 0.314532 0.578933 0.551151 0.066 Uiso 0.5178 1 calc R . . C 2
C2A C 0.3682(2) 0.7535(11) 0.5423(4) 0.0462(16) Uani 0.5178 1 d . . . C 2
H2A H 0.389319 0.637683 0.568947 0.055 Uiso 0.5178 1 calc R . . C 2
O4 O 0.500000 1.8026(9) 0.250000 0.1188(19) Uani 1 2 d S T P . .
H4C H 0.492610 1.917817 0.212900 0.178 Uiso 0.5 1 d G . . . .
H4D H 0.518128 1.864603 0.296752 0.178 Uiso 0.5 1 d G . . . .
C13B C 0.3706(3) 1.5853(12) 0.3033(5) 0.0533(17) Uani 0.5178 1 d . . . B 2
H13B H 0.387701 1.700760 0.341613 0.064 Uiso 0.5178 1 calc R . . B 2
C9B C 0.3607(3) 1.2145(13) 0.2259(5) 0.070(2) Uani 0.5178 1 d . . . B 2
H9B H 0.372919 1.077152 0.209748 0.084 Uiso 0.5178 1 calc R . . B 2
C12B C 0.3248(3) 1.599(2) 0.2856(7) 0.056(2) Uani 0.5178 1 d . . . B 2
H12B H 0.312362 1.729257 0.305668 0.068 Uiso 0.5178 1 calc R . . B 2
C11B C 0.2989(4) 1.423(2) 0.2397(7) 0.063(3) Uani 0.5178 1 d . . . B 2
H11B H 0.268390 1.433989 0.227989 0.075 Uiso 0.5178 1 calc R . . B 2
C10B C 0.3156(3) 1.2311(16) 0.2097(5) 0.073(2) Uani 0.5178 1 d . . . B 2
H10B H 0.296806 1.110532 0.178354 0.087 Uiso 0.5178 1 calc R . . B 2
O2A O 0.4526(8) 1.247(4) 0.5387(13) 0.103(7) Uani 0.5178 1 d . . . A 1
O1A O 0.4563(7) 0.858(3) 0.6020(14) 0.092(6) Uani 0.5178 1 d . . . A 1
O3B O 0.4447(5) 0.923(4) 0.4419(13) 0.062(4) Uani 0.4821 1 d . . . A 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 O1B 1.46(2) . ?
S1 O3A 1.407(17) . ?
S1 O2B 1.435(19) . ?
S1 C1 1.745(3) . ?
S1 O2A 1.43(2) . ?
S1 O1A 1.41(2) . ?
S1 O3B 1.459(19) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.459(5) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.345(13) . ?
C13A C8 1.524(8) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.339(16) . ?
C11A H11A 0.9300 . ?
C11A C10A 1.42(3) . ?
C10A H10A 0.9300 . ?
C10A C9A 1.400(18) . ?
C9A H9A 0.9300 . ?
C9A C8 1.183(10) . ?
C1 C6B 1.594(7) . ?
C1 C2B 1.246(8) . ?
C1 C6A 1.227(7) . ?
C1 C2A 1.567(7) . ?
C8 C7 1.485(6) . ?
C8 C13B 1.275(8) . ?
C8 C9B 1.577(9) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.333(12) . ?
C4B C3B 1.424(18) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.367(10) . ?
C5B H5B 0.9300 . ?
C2B H2B 0.9300 . ?
C2B C3B 1.366(13) . ?
C3B H3B 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.395(11) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.334(16) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.402(13) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.372(9) . ?
C2A H2A 0.9300 . ?
O4 H4C 0.85(17) 2_655 ?
O4 H4C 0.8497 . ?
O4 H4D 0.85(11) 2_655 ?
O4 H4D 0.8501 . ?
C13B H13B 0.9300 . ?
C13B C12B 1.393(11) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.376(11) . ?
C12B H12B 0.9300 . ?
C12B C11B 1.332(18) . ?
C11B H11B 0.9300 . ?
C11B C10B 1.346(15) . ?
C10B H10B 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
O1B S1 C1 108.5(8) . . ?
O1B S1 O3B 119.4(11) . . ?
O3A S1 C1 104.2(8) . . ?
O3A S1 O2A 121.1(13) . . ?
O3A S1 O1A 106.5(13) . . ?
O2B S1 O1B 112.2(8) . . ?
O2B S1 C1 103.9(9) . . ?
O2B S1 O3B 103.1(13) . . ?
O2A S1 C1 107.0(10) . . ?
O1A S1 C1 103.2(9) . . ?
O1A S1 O2A 113.0(11) . . ?
O3B S1 C1 108.5(6) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
C12A C13A H13A 120.9 . . ?
C12A C13A C8 118.3(8) . . ?
C8 C13A H13A 120.9 . . ?
C13A C12A H12A 119.6 . . ?
C11A C12A C13A 120.7(10) . . ?
C11A C12A H12A 119.6 . . ?
C12A C11A H11A 120.2 . . ?
C12A C11A C10A 119.6(13) . . ?
C10A C11A H11A 120.2 . . ?
C11A C10A H10A 121.4 . . ?
C9A C10A C11A 117.2(14) . . ?
C9A C10A H10A 121.4 . . ?
C10A C9A H9A 117.1 . . ?
C8 C9A C10A 125.9(10) . . ?
C8 C9A H9A 117.1 . . ?
C6B C1 S1 110.4(3) . . ?
C2B C1 S1 133.7(4) . . ?
C2B C1 C6B 113.7(5) . . ?
C6A C1 S1 130.8(4) . . ?
C6A C1 C2A 116.9(5) . . ?
C2A C1 S1 109.6(3) . . ?
C9A C8 C13A 117.9(7) . . ?
C9A C8 C7 131.2(6) . . ?
C7 C8 C13A 110.2(5) . . ?
C7 C8 C9B 110.2(5) . . ?
C13B C8 C7 134.8(5) . . ?
C13B C8 C9B 111.9(6) . . ?
C5B C4B H4B 120.3 . . ?
C5B C4B C3B 119.5(8) . . ?
C3B C4B H4B 120.3 . . ?
C1 C6B H6B 121.1 . . ?
C5B C6B C1 117.8(6) . . ?
C5B C6B H6B 121.1 . . ?
C4B C5B C6B 121.8(7) . . ?
C4B C5B H5B 119.1 . . ?
C6B C5B H5B 119.1 . . ?
C1 C2B H2B 116.3 . . ?
C1 C2B C3B 127.5(8) . . ?
C3B C2B H2B 116.3 . . ?
C4B C3B H3B 120.5 . . ?
C2B C3B C4B 118.9(11) . . ?
C2B C3B H3B 120.5 . . ?
N1 C7 C8 114.0(3) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C1 C6A H6A 117.9 . . ?
C1 C6A C5A 124.2(7) . . ?
C5A C6A H6A 117.9 . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A C6A 121.6(9) . . ?
C4A C5A H5A 119.2 . . ?
C5A C4A H4A 120.3 . . ?
C5A C4A C3A 119.3(8) . . ?
C3A C4A H4A 120.3 . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A C4A 120.1(7) . . ?
C2A C3A H3A 119.9 . . ?
C1 C2A H2A 121.6 . . ?
C3A C2A C1 116.7(5) . . ?
C3A C2A H2A 121.6 . . ?
H4C O4 H4C 81.7 . 2_655 ?
H4C O4 H4D 104.5 . . ?
H4C O4 H4D 30.1 . 2_655 ?
H4C O4 H4D 104.5 2_655 2_655 ?
H4D O4 H4C 30.1 . 2_655 ?
H4D O4 H4D 132.0 . 2_655 ?
C8 C13B H13B 116.7 . . ?
C8 C13B C12B 126.6(7) . . ?
C12B C13B H13B 116.7 . . ?
C8 C9B H9B 120.4 . . ?
C10B C9B C8 119.2(6) . . ?
C10B C9B H9B 120.4 . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B C13B 119.5(10) . . ?
C11B C12B H12B 120.3 . . ?
C12B C11B H11B 119.0 . . ?
C12B C11B C10B 122.1(11) . . ?
C10B C11B H11B 119.0 . . ?
C9B C10B H10B 120.3 . . ?
C11B C10B C9B 119.5(8) . . ?
C11B C10B H10B 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_PLAT332_BSBA                
;
PROBLEM:  Large Phenyl C-C Range     C1        -C6A      .       0.34 Ang.,
C1        -C6B      .       0.35 Ang., C8        -C13B     .       0.30 Ang., 
C8        -C13A     .       0.34 Ang.     
RESPONSE: Atoms, mentioned in these alerts, being a part of a two-point 
disordered bezene ring, are modeled. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_N2SBA
_database_code_depnum_ccdc_archive 'CCDC 1872173'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 O3 S, C7 H10 N'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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'
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                   16.352(19)
_cell_length_b                   10.823(12)
_cell_length_c                   9.736(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.376(13)
_cell_angle_gamma                90
_cell_volume                     1661(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6727
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1487 before and 0.0403 after correction. The Ratio of minimum to maximum transmission is 0.9267. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21873
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.862
_diffrn_reflns_theta_min         1.291
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.937
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2877
_reflns_number_total             4088
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.053
_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)+(0.0820P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C17(H17), C8(H8), C13(H13), C3(H3), C7(H7), C16(H16), C14(H14),
 C15(H15), C6(H6), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.38197(2) 0.60048(4) 0.15596(4) 0.05132(16) Uani 1 1 d . . . . .
O2 O 0.41672(8) 0.72546(12) 0.16281(16) 0.0691(4) Uani 1 1 d . . . . .
O3 O 0.39158(9) 0.53830(15) 0.02729(16) 0.0808(4) Uani 1 1 d . . . . .
N1 N 0.51982(8) 0.80490(14) 0.43340(17) 0.0603(4) Uani 1 1 d . . . . .
H1A H 0.546156 0.871703 0.413146 0.090 Uiso 1 1 calc GR . . . .
H1B H 0.481417 0.827370 0.478460 0.090 Uiso 1 1 calc GR . . . .
H1C H 0.494178 0.765899 0.353045 0.090 Uiso 1 1 calc GR . . . .
O1 O 0.41570(8) 0.53003(18) 0.28480(17) 0.0969(6) Uani 1 1 d . . . . .
C2 C 0.23093(9) 0.55447(15) 0.21987(16) 0.0478(4) Uani 1 1 d . . . . .
H2 H 0.262630 0.504221 0.292026 0.057 Uiso 1 1 calc R . . . .
C1 C 0.27009(9) 0.61613(14) 0.13268(17) 0.0457(3) Uani 1 1 d . . . . .
C9 C 0.14111(10) 0.56665(16) 0.20098(17) 0.0507(4) Uani 1 1 d . . . . .
C12 C 0.64688(10) 0.67167(16) 0.45202(17) 0.0514(4) Uani 1 1 d . . . . .
C10 C 0.09439(10) 0.64680(18) 0.0909(2) 0.0594(4) Uani 1 1 d . . . . .
C17 C 0.71375(11) 0.74573(18) 0.4352(2) 0.0618(5) Uani 1 1 d . . . . .
H17 H 0.720077 0.825841 0.471034 0.074 Uiso 1 1 calc R . . . .
C8 C 0.22329(11) 0.69360(18) 0.0205(2) 0.0635(5) Uani 1 1 d . . . . .
H8 H 0.250661 0.733811 -0.039190 0.076 Uiso 1 1 calc R . . . .
C13 C 0.63887(11) 0.55143(18) 0.39778(19) 0.0601(4) Uani 1 1 d . . . . .
H13 H 0.594397 0.502028 0.408315 0.072 Uiso 1 1 calc R . . . .
C3 C 0.09713(12) 0.5025(2) 0.2868(2) 0.0690(5) Uani 1 1 d . . . . .
H3 H 0.126526 0.449352 0.357875 0.083 Uiso 1 1 calc R . . . .
C7 C 0.13768(11) 0.7083(2) 0.0013(2) 0.0740(6) Uani 1 1 d . . . . .
H7 H 0.107347 0.759215 -0.071438 0.089 Uiso 1 1 calc R . . . .
C11 C 0.58325(12) 0.7203(2) 0.5268(2) 0.0704(5) Uani 1 1 d . . . . .
H11A H 0.553762 0.651336 0.555668 0.085 Uiso 1 1 calc R . . . .
H11B H 0.613091 0.764506 0.612090 0.085 Uiso 1 1 calc R . . . .
C16 C 0.77095(11) 0.6986(2) 0.3643(2) 0.0760(6) Uani 1 1 d . . . . .
H16 H 0.815147 0.747715 0.352063 0.091 Uiso 1 1 calc R . . . .
C14 C 0.69597(13) 0.5046(2) 0.3287(2) 0.0691(5) Uani 1 1 d . . . . .
H14 H 0.690139 0.424248 0.293594 0.083 Uiso 1 1 calc R . . . .
C15 C 0.76182(13) 0.5784(2) 0.3121(2) 0.0765(6) Uani 1 1 d . . . . .
H15 H 0.800320 0.547264 0.265722 0.092 Uiso 1 1 calc R . . . .
C6 C 0.00480(12) 0.6615(2) 0.0726(3) 0.0843(7) Uani 1 1 d . . . . .
H6 H -0.026151 0.713838 0.001971 0.101 Uiso 1 1 calc R . . . .
C5 C -0.03517(13) 0.5993(3) 0.1581(3) 0.0936(8) Uani 1 1 d . . . . .
H5 H -0.093101 0.610130 0.145675 0.112 Uiso 1 1 calc R . . . .
C4 C 0.01043(14) 0.5188(3) 0.2649(3) 0.0874(7) Uani 1 1 d . . . . .
H4 H -0.017871 0.476195 0.321431 0.105 Uiso 1 1 calc R . . . .


_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 O2 1.462(2) . ?
S1 O3 1.4668(19) . ?
S1 O1 1.4465(18) . ?
S1 C1 1.791(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C11 1.497(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.365(2) . ?
C2 C9 1.437(3) . ?
C1 C8 1.428(2) . ?
C9 C10 1.432(3) . ?
C9 C3 1.420(3) . ?
C12 C17 1.400(3) . ?
C12 C13 1.397(3) . ?
C12 C11 1.514(3) . ?
C10 C7 1.426(3) . ?
C10 C6 1.437(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.398(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.372(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C7 H7 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C15 1.390(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.364(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.409(4) . ?
C4 H4 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
O2 S1 O3 109.58(10) . . ?
O2 S1 C1 106.85(8) . . ?
O3 S1 C1 105.81(8) . . ?
O1 S1 O2 113.20(11) . . ?
O1 S1 O3 113.35(14) . . ?
O1 S1 C1 107.54(8) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N1 H1A 109.5 . . ?
C11 N1 H1B 109.5 . . ?
C11 N1 H1C 109.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C9 120.50(15) . . ?
C9 C2 H2 119.8 . . ?
C2 C1 S1 120.45(12) . . ?
C2 C1 C8 121.21(16) . . ?
C8 C1 S1 118.33(13) . . ?
C10 C9 C2 118.41(15) . . ?
C3 C9 C2 122.68(17) . . ?
C3 C9 C10 118.91(17) . . ?
C17 C12 C11 120.98(19) . . ?
C13 C12 C17 119.14(18) . . ?
C13 C12 C11 119.88(17) . . ?
C9 C10 C6 118.96(18) . . ?
C7 C10 C9 119.19(16) . . ?
C7 C10 C6 121.84(18) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C1 C8 H8 120.2 . . ?
C7 C8 C1 119.52(17) . . ?
C7 C8 H8 120.2 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.14(18) . . ?
C14 C13 H13 119.4 . . ?
C9 C3 H3 119.9 . . ?
C4 C3 C9 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C10 C7 H7 119.4 . . ?
C8 C7 C10 121.14(17) . . ?
C8 C7 H7 119.4 . . ?
N1 C11 C12 111.98(16) . . ?
N1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.06(19) . . ?
C15 C16 H16 120.0 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C6 H6 119.8 . . ?
C5 C6 C10 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?

_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_N2SNm
_database_code_depnum_ccdc_archive 'CCDC 1872171'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 O3 S, C11 H12 N'
_chemical_formula_sum            'C21 H19 N O3 S'
_chemical_formula_weight         365.43
_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'
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                   18.261(15)
_cell_length_b                   7.799(6)
_cell_length_c                   12.919(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.200(11)
_cell_angle_gamma                90
_cell_volume                     1758(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.97
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1404 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.8047. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17863
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.861
_diffrn_reflns_theta_max         24.861
_diffrn_reflns_theta_min         1.167
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2208
_reflns_number_total             3015
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.096
_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)+(0.0752P)²+0.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C8(H8), C15(H15), C19(H19), C14(H14), C16(H16), C7(H7),
 C6(H6), C3(H3), C18(H18), C17(H17), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.56481(4) 0.73091(7) 0.40474(5) 0.0318(2) Uani 1 1 d . . . . .
O4 O 0.52807(11) 0.8429(2) 0.46427(14) 0.0461(5) Uani 1 1 d . . . . .
O2 O 0.58355(11) 0.8209(2) 0.31796(14) 0.0469(5) Uani 1 1 d . . . . .
O3 O 0.52127(11) 0.5750(2) 0.36735(15) 0.0457(5) Uani 1 1 d . . . . .
N1 N 0.45506(12) 0.7993(3) 0.62829(17) 0.0404(6) Uani 1 1 d . . . . .
H1A H 0.464779 0.861037 0.688768 0.061 Uiso 1 1 calc GR . . . .
H1B H 0.479199 0.845231 0.584408 0.061 Uiso 1 1 calc GR . . . .
H1C H 0.471446 0.692334 0.644622 0.061 Uiso 1 1 calc GR . . . .
C12 C 0.32519(15) 0.7054(3) 0.63484(19) 0.0321(6) Uani 1 1 d . . . . .
C1 C 0.65219(15) 0.6700(3) 0.5013(2) 0.0333(6) Uani 1 1 d . . . . .
C20 C 0.24368(15) 0.7019(3) 0.5886(2) 0.0356(6) Uani 1 1 d . . . . .
C11 C 0.37219(15) 0.7979(3) 0.5740(2) 0.0359(6) Uani 1 1 d . . . . .
H11A H 0.363077 0.744571 0.503473 0.043 Uiso 1 1 calc R . . . .
H11B H 0.354395 0.915497 0.562208 0.043 Uiso 1 1 calc R . . . .
C13 C 0.35756(16) 0.6219(3) 0.7311(2) 0.0372(6) Uani 1 1 d . . . . .
H13 H 0.410396 0.626421 0.762408 0.045 Uiso 1 1 calc R . . . .
C21 C 0.19828(16) 0.6107(3) 0.6428(2) 0.0423(7) Uani 1 1 d . . . . .
C2 C 0.72116(16) 0.7213(3) 0.4930(2) 0.0402(7) Uani 1 1 d . . . . .
H2 H 0.723582 0.780909 0.431690 0.048 Uiso 1 1 calc R . . . .
C9 C 0.79116(16) 0.6844(3) 0.5784(2) 0.0425(7) Uani 1 1 d . . . . .
C10 C 0.78407(17) 0.5903(3) 0.6696(2) 0.0471(7) Uani 1 1 d . . . . .
C8 C 0.64724(17) 0.5746(3) 0.5931(2) 0.0447(7) Uani 1 1 d . . . . .
H8 H 0.599729 0.539328 0.598004 0.054 Uiso 1 1 calc R . . . .
C15 C 0.23558(19) 0.5239(3) 0.7412(2) 0.0489(8) Uani 1 1 d . . . . .
H15 H 0.206645 0.462444 0.776813 0.059 Uiso 1 1 calc R . . . .
C19 C 0.20504(17) 0.7845(4) 0.4891(2) 0.0479(7) Uani 1 1 d . . . . .
H19 H 0.233295 0.844958 0.451971 0.057 Uiso 1 1 calc R . . . .
C14 C 0.31258(19) 0.5301(3) 0.7833(2) 0.0474(7) Uani 1 1 d . . . . .
H14 H 0.336109 0.472688 0.847641 0.057 Uiso 1 1 calc R . . . .
C16 C 0.11805(19) 0.6069(4) 0.5969(3) 0.0597(9) Uani 1 1 d . . . . .
H16 H 0.088321 0.547980 0.632497 0.072 Uiso 1 1 calc R . . . .
C7 C 0.71234(18) 0.5351(4) 0.6738(2) 0.0525(8) Uani 1 1 d . . . . .
H7 H 0.708824 0.470309 0.732542 0.063 Uiso 1 1 calc R . . . .
C6 C 0.8529(2) 0.5562(4) 0.7564(3) 0.0675(10) Uani 1 1 d . . . . .
H6 H 0.850357 0.493026 0.816321 0.081 Uiso 1 1 calc R . . . .
C3 C 0.86249(19) 0.7430(4) 0.5752(3) 0.0629(9) Uani 1 1 d . . . . .
H3 H 0.867053 0.803691 0.515432 0.075 Uiso 1 1 calc R . . . .
C18 C 0.1274(2) 0.7763(4) 0.4476(3) 0.0658(10) Uani 1 1 d . . . . .
H18 H 0.103505 0.830736 0.382247 0.079 Uiso 1 1 calc R . . . .
C17 C 0.0830(2) 0.6878(5) 0.5012(3) 0.0707(10) Uani 1 1 d . . . . .
H17 H 0.029917 0.683992 0.472146 0.085 Uiso 1 1 calc R . . . .
C5 C 0.9209(2) 0.6157(5) 0.7511(3) 0.0778(12) Uani 1 1 d . . . . .
H5 H 0.965017 0.593924 0.807774 0.093 Uiso 1 1 calc R . . . .
C4 C 0.9261(2) 0.7099(5) 0.6614(4) 0.0776(11) Uani 1 1 d . . . . .
H4 H 0.973605 0.751008 0.660017 0.093 Uiso 1 1 calc R . . . .


_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 O4 1.4524(19) . ?
S1 O2 1.447(2) . ?
S1 O3 1.455(2) . ?
S1 C1 1.775(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C11 1.468(3) . ?
C12 C20 1.431(4) . ?
C12 C11 1.508(4) . ?
C12 C13 1.373(3) . ?
C1 C2 1.356(4) . ?
C1 C8 1.425(4) . ?
C20 C21 1.423(4) . ?
C20 C19 1.425(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.403(4) . ?
C21 C15 1.424(4) . ?
C21 C16 1.409(4) . ?
C2 H2 0.9300 . ?
C2 C9 1.450(4) . ?
C9 C10 1.426(4) . ?
C9 C3 1.393(4) . ?
C10 C7 1.395(4) . ?
C10 C6 1.440(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.364(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.350(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.361(4) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.367(5) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.347(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.396(5) . ?
C17 H17 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.398(6) . ?
C4 H4 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
O4 S1 O3 112.67(13) . . ?
O4 S1 C1 104.39(12) . . ?
O2 S1 O4 111.77(12) . . ?
O2 S1 O3 112.29(12) . . ?
O2 S1 C1 107.78(13) . . ?
O3 S1 C1 107.41(11) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N1 H1A 109.5 . . ?
C11 N1 H1B 109.5 . . ?
C11 N1 H1C 109.5 . . ?
C20 C12 C11 118.3(2) . . ?
C13 C12 C20 119.0(2) . . ?
C13 C12 C11 122.7(2) . . ?
C2 C1 S1 121.8(2) . . ?
C2 C1 C8 120.6(3) . . ?
C8 C1 S1 117.4(2) . . ?
C21 C20 C12 119.3(2) . . ?
C21 C20 C19 117.7(3) . . ?
C19 C20 C12 123.0(2) . . ?
N1 C11 C12 114.8(2) . . ?
N1 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C20 C21 C15 118.8(3) . . ?
C16 C21 C20 119.2(3) . . ?
C16 C21 C15 121.9(3) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C9 120.7(3) . . ?
C9 C2 H2 119.6 . . ?
C10 C9 C2 117.2(3) . . ?
C3 C9 C2 122.3(3) . . ?
C3 C9 C10 120.5(3) . . ?
C9 C10 C6 117.8(3) . . ?
C7 C10 C9 120.4(3) . . ?
C7 C10 C6 121.8(3) . . ?
C1 C8 H8 120.1 . . ?
C7 C8 C1 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C21 C15 H15 119.7 . . ?
C14 C15 C21 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C21 C16 H16 119.3 . . ?
C17 C16 C21 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C10 C7 H7 119.4 . . ?
C8 C7 C10 121.1(3) . . ?
C8 C7 H7 119.4 . . ?
C10 C6 H6 119.9 . . ?
C5 C6 C10 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C9 C3 H3 120.4 . . ?
C4 C3 C9 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C19 C18 H18 119.4 . . ?
C19 C18 C17 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?

_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_BSNm
_database_code_depnum_ccdc_archive 'CCDC 1872170'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 O3 S, C11 H12 N'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.432(8)
_cell_length_b                   9.545(14)
_cell_length_c                   15.32(2)
_cell_angle_alpha                96.31(2)
_cell_angle_beta                 93.878(19)
_cell_angle_gamma                97.640(19)
_cell_volume                     779.6(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2972
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1414 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.8742. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13527
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        23.071
_diffrn_reflns_theta_max         23.071
_diffrn_reflns_theta_min         1.342
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1586
_reflns_number_total             2155
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.056
_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)+(0.0421P)²+0.4374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C15(H15), C9(H9), C4(H4), C3(H3), C14(H14), C10(H10), C5(H5),
 C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.48014(13) 0.09661(9) 0.37988(5) 0.0436(3) Uani 1 1 d . . . . .
O3 O 0.2127(4) 0.0687(3) 0.38652(14) 0.0627(7) Uani 1 1 d . . . . .
O2 O 0.5904(4) 0.2303(3) 0.43171(14) 0.0602(6) Uani 1 1 d . . . . .
O1 O 0.6076(4) -0.0221(2) 0.39806(14) 0.0605(7) Uani 1 1 d . . . . .
N1 N 1.0041(4) 0.1817(3) 0.54129(16) 0.0525(7) Uani 1 1 d . . . . .
H1A H 1.095835 0.145814 0.500708 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.864620 0.202613 0.515082 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.966051 0.117915 0.578273 0.063 Uiso 1 1 calc GR . . . .
C1 C 0.5136(5) 0.1206(3) 0.26804(18) 0.0375(7) Uani 1 1 d . . . . .
C16 C 1.0199(5) 0.3399(3) 0.7489(2) 0.0465(8) Uani 1 1 d . . . . .
C8 C 0.9972(6) 0.3744(3) 0.6611(2) 0.0509(9) Uani 1 1 d . . . . .
C6 C 0.7281(6) 0.1967(4) 0.2448(2) 0.0529(9) Uani 1 1 d . . . . .
H6 H 0.856040 0.234703 0.287687 0.063 Uiso 1 1 calc R . . . .
C2 C 0.3279(6) 0.0641(4) 0.2036(2) 0.0510(9) Uani 1 1 d . . . . .
H2 H 0.182414 0.012619 0.218556 0.061 Uiso 1 1 calc R . . . .
C17 C 0.8750(6) 0.3999(4) 0.8133(2) 0.0531(9) Uani 1 1 d . . . . .
C7 C 1.1471(6) 0.3127(4) 0.5909(2) 0.0569(9) Uani 1 1 d . . . . .
H7A H 1.188439 0.382275 0.550678 0.068 Uiso 1 1 calc R . . . .
H7B H 1.301510 0.290487 0.618064 0.068 Uiso 1 1 calc R . . . .
C15 C 1.1851(6) 0.2439(4) 0.7763(2) 0.0531(9) Uani 1 1 d . . . . .
H15 H 1.278633 0.200102 0.735514 0.064 Uiso 1 1 calc R . . . .
C9 C 0.8325(7) 0.4659(4) 0.6404(3) 0.0665(10) Uani 1 1 d . . . . .
H9 H 0.818558 0.489739 0.583202 0.080 Uiso 1 1 calc R . . . .
C4 C 0.5660(7) 0.1607(4) 0.0938(2) 0.0613(10) Uani 1 1 d . . . . .
H4 H 0.582512 0.175536 0.035391 0.074 Uiso 1 1 calc R . . . .
C3 C 0.3564(6) 0.0836(4) 0.1162(2) 0.0620(10) Uani 1 1 d . . . . .
H3 H 0.231269 0.043591 0.072685 0.074 Uiso 1 1 calc R . . . .
C14 C 1.2047(7) 0.2172(4) 0.8617(3) 0.0646(10) Uani 1 1 d . . . . .
H14 H 1.313041 0.155756 0.878833 0.078 Uiso 1 1 calc R . . . .
C10 C 0.6852(7) 0.5242(4) 0.7025(3) 0.0752(12) Uani 1 1 d . . . . .
H10 H 0.573170 0.584081 0.686035 0.090 Uiso 1 1 calc R . . . .
C5 C 0.7528(6) 0.2166(4) 0.1572(2) 0.0630(10) Uani 1 1 d . . . . .
H5 H 0.897342 0.268186 0.141580 0.076 Uiso 1 1 calc R . . . .
C11 C 0.7062(7) 0.4931(4) 0.7869(3) 0.0746(12) Uani 1 1 d . . . . .
H11 H 0.609386 0.533069 0.828075 0.090 Uiso 1 1 calc R . . . .
C12 C 0.9014(8) 0.3686(5) 0.9005(3) 0.0757(12) Uani 1 1 d . . . . .
H12 H 0.806615 0.408319 0.942440 0.091 Uiso 1 1 calc R . . . .
C13 C 1.0648(8) 0.2806(5) 0.9239(3) 0.0810(12) Uani 1 1 d . . . . .
H13 H 1.083671 0.262300 0.982228 0.097 Uiso 1 1 calc R . . . .


_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 O3 1.454(3) . ?
S1 O2 1.459(3) . ?
S1 O1 1.447(3) . ?
S1 C1 1.771(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.482(4) . ?
C1 C6 1.379(4) . ?
C1 C2 1.374(4) . ?
C16 C8 1.419(5) . ?
C16 C17 1.422(4) . ?
C16 C15 1.440(5) . ?
C8 C7 1.508(5) . ?
C8 C9 1.376(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(5) . ?
C17 C11 1.429(5) . ?
C17 C12 1.402(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C14 1.359(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.400(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.357(5) . ?
C4 C5 1.366(5) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.395(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(6) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.358(6) . ?
C13 H13 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
O3 S1 O2 111.56(14) . . ?
O3 S1 C1 105.11(12) . . ?
O2 S1 C1 106.35(15) . . ?
O1 S1 O3 113.13(16) . . ?
O1 S1 O2 113.04(16) . . ?
O1 S1 C1 106.97(13) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
C6 C1 S1 120.0(2) . . ?
C2 C1 S1 120.8(2) . . ?
C2 C1 C6 119.2(3) . . ?
C8 C16 C17 120.1(3) . . ?
C8 C16 C15 122.4(3) . . ?
C17 C16 C15 117.5(3) . . ?
C16 C8 C7 121.6(3) . . ?
C9 C8 C16 118.6(3) . . ?
C9 C8 C7 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C16 C17 C11 118.3(3) . . ?
C12 C17 C16 120.2(3) . . ?
C12 C17 C11 121.5(4) . . ?
N1 C7 C8 110.5(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C8 C9 H9 118.9 . . ?
C8 C9 C10 122.2(4) . . ?
C10 C9 H9 118.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.0 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C17 C11 H11 119.6 . . ?
C10 C11 C17 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C17 C12 H12 119.9 . . ?
C13 C12 C17 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_THETM01_BSNm                
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5514   
RESPONSE: The crystal was poorly diffracting at higher Bragg angles
and the problem could not be solved even after collecting
fresh data sets on variuos crystals.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_N2SPh
_database_code_depnum_ccdc_archive 'CCDC 1872172'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 O3 S, C8 H12 N'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8765(17)
_cell_length_b                   7.649(2)
_cell_length_c                   18.388(5)
_cell_angle_alpha                92.938(4)
_cell_angle_beta                 94.963(4)
_cell_angle_gamma                93.182(4)
_cell_volume                     820.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6763
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1850 before and 0.0432 after correction. The Ratio of minimum to maximum transmission is 0.9529. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.980
_diffrn_reflns_theta_min         1.113
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2893
_reflns_number_total             3704
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.110
_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)+(0.0670P)²+0.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C7(H7), C3(H3), C18(H18), C14(H14), C6(H6), C4(H4), C15(H15),
 C16(H16), C17(H17), C5(H5)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.82640(9) 0.27264(7) 0.59292(3) 0.04094(17) Uani 1 1 d . . . . .
O1 O 0.9604(3) 0.4244(2) 0.57261(8) 0.0546(4) Uani 1 1 d . . . . .
O2 O 0.8824(3) 0.1141(2) 0.55372(9) 0.0609(5) Uani 1 1 d . . . . .
N1 N 0.2655(3) 0.2533(2) 0.46778(9) 0.0420(4) Uani 1 1 d . . . . .
H1A H 0.176748 0.343300 0.462856 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.347650 0.265319 0.510913 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.178512 0.153725 0.465142 0.063 Uiso 1 1 calc GR . . . .
O3 O 0.5845(3) 0.3011(3) 0.58938(9) 0.0724(6) Uani 1 1 d . . . . .
C2 C 0.7779(3) 0.3029(2) 0.73910(10) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.638456 0.349499 0.725755 0.040 Uiso 1 1 calc R . . . .
C9 C 0.8491(3) 0.2897(2) 0.81382(10) 0.0340(4) Uani 1 1 d . . . . .
C10 C 1.0585(3) 0.2132(3) 0.83311(11) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.9113(3) 0.2482(2) 0.68623(10) 0.0328(4) Uani 1 1 d . . . . .
C8 C 1.1225(3) 0.1756(3) 0.70523(12) 0.0414(5) Uani 1 1 d . . . . .
H8 H 1.213792 0.140363 0.668956 0.050 Uiso 1 1 calc R . . . .
C13 C 0.4299(3) 0.2466(3) 0.27009(11) 0.0395(4) Uani 1 1 d . . . . .
C7 C 1.1919(3) 0.1575(3) 0.77672(12) 0.0435(5) Uani 1 1 d . . . . .
H7 H 1.329862 0.107527 0.788860 0.052 Uiso 1 1 calc R . . . .
C3 C 0.7182(4) 0.3501(3) 0.86984(11) 0.0469(5) Uani 1 1 d . . . . .
H3 H 0.581377 0.401650 0.857708 0.056 Uiso 1 1 calc R . . . .
C18 C 0.3348(4) 0.1698(3) 0.20407(13) 0.0480(5) Uani 1 1 d . . . . .
H18 H 0.190406 0.112391 0.201347 0.058 Uiso 1 1 calc R . . . .
C12 C 0.2869(4) 0.2419(3) 0.33506(11) 0.0455(5) Uani 1 1 d . . . . .
H12A H 0.189378 0.340173 0.333630 0.055 Uiso 1 1 calc R . . . .
H12B H 0.188204 0.135280 0.329956 0.055 Uiso 1 1 calc R . . . .
C14 C 0.6455(4) 0.3306(3) 0.27258(13) 0.0499(5) Uani 1 1 d . . . . .
H14 H 0.712881 0.383353 0.316485 0.060 Uiso 1 1 calc R . . . .
C6 C 1.1258(4) 0.1972(3) 0.90796(12) 0.0561(6) Uani 1 1 d . . . . .
H6 H 1.262072 0.146224 0.921460 0.067 Uiso 1 1 calc R . . . .
C11 C 0.4217(4) 0.2491(3) 0.40834(12) 0.0486(5) Uani 1 1 d . . . . .
H11A H 0.512289 0.147212 0.411931 0.058 Uiso 1 1 calc R . . . .
H11B H 0.525408 0.353060 0.413611 0.058 Uiso 1 1 calc R . . . .
C4 C 0.7901(5) 0.3338(4) 0.94124(13) 0.0632(7) Uani 1 1 d . . . . .
H4 H 0.702827 0.375178 0.977574 0.076 Uiso 1 1 calc R . . . .
C15 C 0.7606(4) 0.3366(3) 0.21099(16) 0.0599(7) Uani 1 1 d . . . . .
H15 H 0.905569 0.393044 0.213492 0.072 Uiso 1 1 calc R . . . .
C16 C 0.6648(5) 0.2608(4) 0.14629(15) 0.0704(8) Uani 1 1 d . . . . .
H16 H 0.744047 0.265526 0.104720 0.085 Uiso 1 1 calc R . . . .
C17 C 0.4501(5) 0.1769(4) 0.14234(13) 0.0656(7) Uani 1 1 d . . . . .
H17 H 0.383531 0.125390 0.098099 0.079 Uiso 1 1 calc R . . . .
C5 C 0.9950(5) 0.2551(4) 0.96058(13) 0.0691(8) Uani 1 1 d . . . . .
H5 H 1.041436 0.242467 1.009574 0.083 Uiso 1 1 calc R . . . .


_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 O1 1.4495(16) . ?
S1 O2 1.4469(16) . ?
S1 O3 1.4462(17) . ?
S1 C1 1.767(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C11 1.487(3) . ?
C2 H2 0.9300 . ?
C2 C9 1.412(3) . ?
C2 C1 1.364(2) . ?
C9 C10 1.417(3) . ?
C9 C3 1.412(3) . ?
C10 C7 1.416(3) . ?
C10 C6 1.412(3) . ?
C1 C8 1.411(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.359(3) . ?
C13 C18 1.380(3) . ?
C13 C12 1.520(3) . ?
C13 C14 1.384(3) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.358(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.373(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.500(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.359(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.403(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.358(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C5 H5 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
O1 S1 C1 105.76(9) . . ?
O2 S1 O1 111.47(10) . . ?
O2 S1 C1 106.51(10) . . ?
O3 S1 O1 112.24(12) . . ?
O3 S1 O2 114.48(12) . . ?
O3 S1 C1 105.63(9) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N1 H1A 109.5 . . ?
C11 N1 H1B 109.5 . . ?
C11 N1 H1C 109.5 . . ?
C9 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C9 120.73(17) . . ?
C2 C9 C10 118.88(17) . . ?
C2 C9 C3 122.07(18) . . ?
C3 C9 C10 119.05(18) . . ?
C7 C10 C9 118.73(18) . . ?
C6 C10 C9 118.44(19) . . ?
C6 C10 C7 122.83(19) . . ?
C2 C1 S1 120.54(14) . . ?
C2 C1 C8 120.58(18) . . ?
C8 C1 S1 118.85(14) . . ?
C1 C8 H8 120.1 . . ?
C7 C8 C1 119.73(18) . . ?
C7 C8 H8 120.1 . . ?
C18 C13 C12 118.00(19) . . ?
C18 C13 C14 118.2(2) . . ?
C14 C13 C12 123.71(19) . . ?
C10 C7 H7 119.3 . . ?
C8 C7 C10 121.31(18) . . ?
C8 C7 H7 119.3 . . ?
C9 C3 H3 119.7 . . ?
C4 C3 C9 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C11 C12 C13 114.95(18) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C10 C6 H6 119.4 . . ?
C5 C6 C10 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
N1 C11 C12 110.35(18) . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
