# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_DG225_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1862562'
loop_
_audit_author_name
_audit_author_address
'Dilip K Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2018-08-17 deposited with the CCDC.	2019-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N O2 S'
_chemical_formula_sum            'C13 H11 N O2 S'
_chemical_formula_weight         245.29

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.091(8)
_cell_length_b                   5.651(4)
_cell_length_c                   17.732(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.197(15)
_cell_angle_gamma                90
_cell_volume                     1196.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1817
_cell_measurement_theta_min      1.905
_cell_measurement_theta_max      26.604

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5086
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         26.604
_diffrn_reflns_theta_full        26.604
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1942
_reflns_number_gt                994
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3602P] 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         1817
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2384
_refine_ls_wR_factor_gt          0.2069
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.35988(14) 0.6642(3) 0.28914(9) 0.0769(7) Uani 1 1 d . . . . .
O002 O 0.5257(3) 0.2755(7) 0.4526(2) 0.0596(11) Uani 1 1 d . . . . .
O003 O 0.2486(3) 0.3680(8) 0.3756(2) 0.0774(14) Uani 1 1 d . . . . .
N004 N 0.3263(4) 0.0615(9) 0.4463(3) 0.0564(14) Uani 1 1 d . . . . .
C1 C 0.5678(4) 0.6934(8) 0.3673(3) 0.0399(13) Uani 1 1 d . . . . .
H5 H 0.6335 0.6643 0.4011 0.048 Uiso 1 1 calc R U . . .
C006 C 0.4480(4) 0.3628(10) 0.4099(3) 0.0463(14) Uani 1 1 d . . . . .
C007 C 0.4618(4) 0.5614(10) 0.3604(3) 0.0493(15) Uani 1 1 d . . . . .
C008 C 0.3307(5) 0.2609(11) 0.4086(3) 0.0533(15) Uani 1 1 d . . . . .
C009 C 0.1775(5) -0.0062(11) 0.5243(4) 0.0608(17) Uani 1 1 d . . . . .
C00A C 0.2195(5) -0.0594(11) 0.4507(3) 0.0653(18) Uani 1 1 d . . . . .
H00A H 0.2297 -0.2288 0.4464 0.078 Uiso 1 1 calc R U . . .
H3 H 0.1638 -0.0095 0.4081 0.078 Uiso 1 1 calc R U . . .
C00B C 0.1976(5) -0.1591(13) 0.5848(4) 0.0744(19) Uani 1 1 d . . . . .
H2 H 0.2378 -0.2974 0.5804 0.089 Uiso 1 1 calc R U . . .
C00C C 0.4458(5) 0.8765(11) 0.2664(3) 0.0660(18) Uani 1 1 d . . . . .
H00C H 0.4251 0.9842 0.2270 0.079 Uiso 1 1 calc R U . . .
C00D C 0.5481(5) 0.8768(11) 0.3107(3) 0.0651(18) Uani 1 1 d . . . . .
H00D H 0.6024 0.9890 0.3047 0.078 Uiso 1 1 calc R U . . .
C00E C 0.1175(6) 0.1969(13) 0.5322(5) 0.082(2) Uani 1 1 d . . . . .
H00E H 0.1034 0.3046 0.4922 0.098 Uiso 1 1 calc R U . . .
C00F C 0.1593(6) -0.1107(17) 0.6516(5) 0.096(3) Uani 1 1 d . . . . .
H00F H 0.1750 -0.2147 0.6925 0.115 Uiso 1 1 calc R U . . .
C00G C 0.0980(7) 0.0901(17) 0.6587(5) 0.097(3) Uani 1 1 d . . . . .
H00G H 0.0703 0.1221 0.7037 0.117 Uiso 1 1 calc R U . . .
C00H C 0.0790(6) 0.2389(14) 0.5990(6) 0.096(3) Uani 1 1 d . . . . .
H00H H 0.0380 0.3760 0.6035 0.115 Uiso 1 1 calc R U . . .
H4 H 0.393(6) -0.014(12) 0.463(4) 0.11(3) Uiso 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
S001 C00C 1.678(6) . ?
S001 C007 1.719(5) . ?
O002 C006 1.213(5) . ?
O003 C008 1.228(6) . ?
N004 C008 1.316(7) . ?
N004 C00A 1.474(7) . ?
N004 H4 0.92(7) . ?
C1 C00D 1.436(7) . ?
C1 C007 1.471(7) . ?
C1 H5 0.9300 . ?
C006 C007 1.451(8) . ?
C006 C008 1.528(8) . ?
C009 C00B 1.369(9) . ?
C009 C00E 1.377(9) . ?
C009 C00A 1.505(8) . ?
C00A H00A 0.9700 . ?
C00A H3 0.9700 . ?
C00B C00F 1.366(10) . ?
C00B H2 0.9300 . ?
C00C C00D 1.355(7) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00H 1.361(10) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.373(11) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.343(11) . ?
C00G H00G 0.9300 . ?
C00H H00H 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
C00C S001 C007 91.1(3) . . ?
C008 N004 C00A 122.0(5) . . ?
C008 N004 H4 117(5) . . ?
C00A N004 H4 120(4) . . ?
C00D C1 C007 105.2(4) . . ?
C00D C1 H5 127.4 . . ?
C007 C1 H5 127.4 . . ?
O002 C006 C007 122.6(5) . . ?
O002 C006 C008 118.7(5) . . ?
C007 C006 C008 118.6(5) . . ?
C006 C007 C1 121.7(4) . . ?
C006 C007 S001 124.6(4) . . ?
C1 C007 S001 113.7(4) . . ?
O003 C008 N004 124.7(6) . . ?
O003 C008 C006 120.0(5) . . ?
N004 C008 C006 115.3(5) . . ?
C00B C009 C00E 118.4(7) . . ?
C00B C009 C00A 120.8(6) . . ?
C00E C009 C00A 120.8(6) . . ?
N004 C00A C009 111.9(5) . . ?
N004 C00A H00A 109.2 . . ?
C009 C00A H00A 109.2 . . ?
N004 C00A H3 109.2 . . ?
C009 C00A H3 109.2 . . ?
H00A C00A H3 107.9 . . ?
C00F C00B C009 120.7(7) . . ?
C00F C00B H2 119.6 . . ?
C009 C00B H2 119.6 . . ?
C00D C00C S001 113.9(5) . . ?
C00D C00C H00C 123.1 . . ?
S001 C00C H00C 123.1 . . ?
C00C C00D C1 116.0(5) . . ?
C00C C00D H00D 122.0 . . ?
C1 C00D H00D 122.0 . . ?
C00H C00E C009 119.6(7) . . ?
C00H C00E H00E 120.2 . . ?
C009 C00E H00E 120.2 . . ?
C00B C00F C00G 120.6(8) . . ?
C00B C00F H00F 119.7 . . ?
C00G C00F H00F 119.7 . . ?
C00H C00G C00F 118.1(9) . . ?
C00H C00G H00G 120.9 . . ?
C00F C00G H00G 120.9 . . ?
C00G C00H C00E 122.5(8) . . ?
C00G C00H H00H 118.7 . . ?
C00E C00H H00H 118.7 . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.069

