# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_5n
_database_code_depnum_ccdc_archive 'CCDC 2194439'
loop_
_audit_author_name
_audit_author_address
'KAMAL Kamal'
;IIT JAMMU
India
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2022-08-03
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.04.25 svn.r3594 for OlexSys, GUI svn.r5751)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 N2 O5 S'
_chemical_formula_sum            'C17 H12 N2 O5 S'
_chemical_formula_weight         356.35
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.173(3)
_cell_length_b                   5.3337(15)
_cell_length_c                   25.755(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.565(10)
_cell_angle_gamma                90.00
_cell_volume                     1527.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8464
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.51
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.7313
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic greenish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43547
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.31
_diffrn_ambient_temperature      108.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3479
_reflns_number_total             3797
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+1.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S001 S 0.49351(3) -0.04357(6) 0.396688(13) 0.01619(10) Uani 1 d . . .
O002 O 0.32146(9) 0.54857(19) 0.46590(4) 0.0187(2) Uani 1 d . . .
O003 O 0.44212(10) -0.2405(2) 0.36262(4) 0.0217(2) Uani 1 d . . .
O004 O 0.11091(10) 0.6570(2) 0.50980(4) 0.0262(2) Uani 1 d . . .
O005 O 0.15487(10) 0.3567(2) 0.26967(4) 0.0262(2) Uani 1 d . . .
O006 O 0.15191(11) 1.0484(2) 0.49695(5) 0.0293(3) Uani 1 d . . .
N9 N 0.12559(11) 0.8359(2) 0.48167(5) 0.0198(2) Uani 1 d . . .
N008 N 0.41004(11) 0.1409(2) 0.42323(5) 0.0184(2) Uani 1 d . . .
C009 C 0.27224(12) 0.4831(3) 0.42417(5) 0.0153(3) Uani 1 d . . .
C00A C 0.32185(12) 0.2705(3) 0.39383(5) 0.0159(3) Uani 1 d . . .
C00B C 0.16514(12) 0.6196(3) 0.39896(5) 0.0158(3) Uani 1 d . . .
C00C C 0.13100(12) 0.5884(3) 0.34569(5) 0.0170(3) Uani 1 d . . .
C00D C 0.10328(12) 0.8011(3) 0.42483(5) 0.0179(3) Uani 1 d . . .
C00E C 0.59486(12) 0.1291(3) 0.36155(6) 0.0184(3) Uani 1 d . . .
C00F C 0.27954(13) 0.2335(3) 0.34321(5) 0.0184(3) Uani 1 d . . .
H00F H 0.3117 0.0989 0.3248 0.022 Uiso 1 calc . . R
C00G C 0.18822(13) 0.3886(3) 0.31608(5) 0.0182(3) Uani 1 d . . .
C00H C 0.01541(13) 0.9530(3) 0.39979(6) 0.0217(3) Uani 1 d . . .
H00H H -0.0237 1.0768 0.4186 0.026 Uiso 1 calc . . R
C00I C 0.04235(13) 0.7378(3) 0.31983(6) 0.0213(3) Uani 1 d . . .
H00I H 0.0207 0.7142 0.2836 0.026 Uiso 1 calc . . R
C00J C 0.58702(14) 0.1057(3) 0.30773(6) 0.0247(3) Uani 1 d . . .
H00J H 0.5317 -0.0081 0.2901 0.030 Uiso 1 calc . . R
C00K C 0.58054(13) -0.1714(3) 0.45032(6) 0.0213(3) Uani 1 d . . .
H00A H 0.5316 -0.2887 0.4685 0.032 Uiso 1 calc . . GR
H00B H 0.6094 -0.0366 0.4742 0.032 Uiso 1 calc . . GR
H00C H 0.6494 -0.2605 0.4383 0.032 Uiso 1 calc . . GR
C00L C 0.67730(14) 0.2881(3) 0.38838(6) 0.0237(3) Uani 1 d . . .
H00L H 0.6822 0.2995 0.4253 0.028 Uiso 1 calc . . R
C00M C -0.01464(14) 0.9209(3) 0.34653(6) 0.0234(3) Uani 1 d . . .
H00M H -0.0742 1.0243 0.3285 0.028 Uiso 1 calc . . R
C00N C 0.74320(15) 0.4148(3) 0.30621(7) 0.0318(4) Uani 1 d . . .
H00N H 0.7931 0.5165 0.2870 0.038 Uiso 1 calc . . R
C00O C 0.75251(16) 0.4303(3) 0.36027(7) 0.0306(4) Uani 1 d . . .
H00O H 0.8104 0.5384 0.3780 0.037 Uiso 1 calc . . R
C00P C 0.66200(15) 0.2528(3) 0.28011(7) 0.0302(4) Uani 1 d . . .
H00P H 0.6572 0.2415 0.2432 0.036 Uiso 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
S001 O003 1.4508(11) . ?
S001 N008 1.5586(12) . ?
S001 C00E 1.7744(15) . ?
S001 C00K 1.7485(15) . ?
O002 C009 1.2104(17) . ?
O004 N9 1.2186(17) . ?
O005 C00G 1.2290(17) . ?
O006 N9 1.2262(17) . ?
N9 C00D 1.4726(18) . ?
N008 C00A 1.3701(17) . ?
C009 C00A 1.5125(19) . ?
C009 C00B 1.4943(19) . ?
C00A C00F 1.3573(19) . ?
C00B C00C 1.3980(19) . ?
C00B C00D 1.3956(19) . ?
C00C C00G 1.4900(19) . ?
C00C C00I 1.390(2) . ?
C00D C00H 1.383(2) . ?
C00E C00J 1.386(2) . ?
C00E C00L 1.386(2) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.4406(19) . ?
C00H H00H 0.9500 . ?
C00H C00M 1.391(2) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.384(2) . ?
C00J H00J 0.9500 . ?
C00J C00P 1.392(2) . ?
C00K H00A 0.9800 . ?
C00K H00B 0.9800 . ?
C00K H00C 0.9800 . ?
C00L H00L 0.9500 . ?
C00L C00O 1.387(2) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00O 1.389(3) . ?
C00N C00P 1.379(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 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
O003 S001 N008 120.25(7) . . ?
O003 S001 C00E 107.57(7) . . ?
O003 S001 C00K 110.66(7) . . ?
N008 S001 C00E 109.54(7) . . ?
N008 S001 C00K 102.13(7) . . ?
C00K S001 C00E 105.78(7) . . ?
O004 N9 O006 125.08(13) . . ?
O004 N9 C00D 118.22(12) . . ?
O006 N9 C00D 116.60(12) . . ?
C00A N008 S001 120.32(10) . . ?
O002 C009 C00A 121.16(12) . . ?
O002 C009 C00B 121.39(13) . . ?
C00B C009 C00A 117.33(12) . . ?
N008 C00A C009 111.87(11) . . ?
C00F C00A N008 128.49(13) . . ?
C00F C00A C009 119.61(12) . . ?
C00C C00B C009 119.94(12) . . ?
C00D C00B C009 122.91(12) . . ?
C00D C00B C00C 116.78(12) . . ?
C00B C00C C00G 119.85(12) . . ?
C00I C00C C00B 121.06(13) . . ?
C00I C00C C00G 119.09(12) . . ?
C00B C00D N9 121.20(12) . . ?
C00H C00D N9 115.70(12) . . ?
C00H C00D C00B 123.06(13) . . ?
C00J C00E S001 118.80(12) . . ?
C00J C00E C00L 121.88(14) . . ?
C00L C00E S001 119.29(11) . . ?
C00A C00F H00F 118.4 . . ?
C00A C00F C00G 123.15(13) . . ?
C00G C00F H00F 118.4 . . ?
O005 C00G C00C 119.48(13) . . ?
O005 C00G C00F 121.74(13) . . ?
C00F C00G C00C 118.77(12) . . ?
C00D C00H H00H 120.7 . . ?
C00D C00H C00M 118.70(14) . . ?
C00M C00H H00H 120.7 . . ?
C00C C00I H00I 119.8 . . ?
C00M C00I C00C 120.47(13) . . ?
C00M C00I H00I 119.8 . . ?
C00E C00J H00J 120.7 . . ?
C00E C00J C00P 118.51(15) . . ?
C00P C00J H00J 120.7 . . ?
S001 C00K H00A 109.5 . . ?
S001 C00K H00B 109.5 . . ?
S001 C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
C00E C00L H00L 120.6 . . ?
C00E C00L C00O 118.75(15) . . ?
C00O C00L H00L 120.6 . . ?
C00H C00M H00M 120.1 . . ?
C00I C00M C00H 119.88(13) . . ?
C00I C00M H00M 120.1 . . ?
C00O C00N H00N 119.7 . . ?
C00P C00N H00N 119.7 . . ?
C00P C00N C00O 120.52(15) . . ?
C00L C00O C00N 120.04(16) . . ?
C00L C00O H00O 120.0 . . ?
C00N C00O H00O 120.0 . . ?
C00J C00P H00P 119.9 . . ?
C00N C00P C00J 120.25(16) . . ?
C00N C00P H00P 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
