# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dm_3_78_0m
_database_code_depnum_ccdc_archive 'CCDC 2062375'
loop_
_audit_author_name
_audit_author_address
'SANDIP KUNDU'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2021-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        DM-3-84
_chemical_formula_moiety         'C22 H17 Cl N2 O'
_chemical_formula_sum            'C22 H17 Cl N2 O'
_chemical_formula_weight         360.82
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4364(17)
_cell_length_b                   12.3676(18)
_cell_length_c                   14.215(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.464
_cell_measurement_theta_min      4.739
_shelx_estimated_absorpt_T_max   0.722
_shelx_estimated_absorpt_T_min   0.511
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1507 before and 0.0949 after correction. The Ratio of minimum to maximum transmission is 0.7161. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'pet ether in DCM'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.4
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20508
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.876
_diffrn_reflns_theta_max         66.876
_diffrn_reflns_theta_min         4.739
_diffrn_ambient_temperature      273.15
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3132
_reflns_number_total             3219
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(7)
_refine_ls_extinction_coef       0.0088(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.034
_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)+(0.0396P)²+0.5515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0850
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C5(H5), C22(H22), C4(H4), C21(H21), C16(H16), C2(H2A),
 C3(H3), C19(H19), C12(H12), C15(H15), C18(H18), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.20101(7) 0.65487(6) 0.73973(5) 0.0349(2) Uani 1 1 d . . . . .
O1 O 0.7089(2) 0.50383(16) 0.54758(12) 0.0296(5) Uani 1 1 d . . . . .
N1 N 0.5773(2) 0.56584(17) 0.43538(15) 0.0217(5) Uani 1 1 d . . . . .
N2 N 0.7153(2) 0.52226(17) 0.24152(15) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.727654 0.533070 0.182458 0.028 Uiso 1 1 calc R . . . .
C10 C 0.4535(3) 0.6613(2) 0.32046(18) 0.0241(6) Uani 1 1 d . . . . .
H10 H 0.427020 0.703998 0.370689 0.029 Uiso 1 1 calc R . . . .
C5 C 0.9396(3) 0.5313(2) 0.25791(19) 0.0242(6) Uani 1 1 d . . . . .
H5 H 0.945198 0.531277 0.192620 0.029 Uiso 1 1 calc R . . . .
C11 C 0.3989(3) 0.6889(2) 0.22818(19) 0.0230(6) Uani 1 1 d . . . . .
C7 C 0.6957(3) 0.5287(2) 0.46400(17) 0.0219(6) Uani 1 1 d . . . . .
C22 C 0.4995(3) 0.6780(2) 0.56575(19) 0.0254(6) Uani 1 1 d . . . . .
H22 H 0.567632 0.724933 0.555459 0.031 Uiso 1 1 calc R . . . .
C1 C 0.8102(3) 0.5280(2) 0.40064(18) 0.0220(6) Uani 1 1 d . . . . .
C6 C 0.8173(3) 0.5281(2) 0.30096(18) 0.0212(6) Uani 1 1 d . . . . .
C9 C 0.5367(3) 0.5822(2) 0.34117(17) 0.0212(6) Uani 1 1 d . . . . .
C4 C 1.0500(3) 0.5346(2) 0.3102(2) 0.0261(6) Uani 1 1 d . . . . .
H4 H 1.129013 0.537683 0.280098 0.031 Uiso 1 1 calc R . . . .
C21 C 0.4120(3) 0.6994(2) 0.6364(2) 0.0285(7) Uani 1 1 d . . . . .
H21 H 0.421239 0.760113 0.674341 0.034 Uiso 1 1 calc R . . . .
C16 C 0.2733(3) 0.7298(2) 0.2249(2) 0.0264(6) Uani 1 1 d . . . . .
H16 H 0.227098 0.737307 0.280406 0.032 Uiso 1 1 calc R . . . .
C2 C 0.9267(3) 0.5296(2) 0.45104(18) 0.0257(6) Uani 1 1 d . . . . .
H2A H 0.923377 0.528187 0.516408 0.031 Uiso 1 1 calc R . . . .
C8 C 0.5871(3) 0.4987(2) 0.27368(18) 0.0214(6) Uani 1 1 d . . . . .
H8A H 0.586794 0.428610 0.304279 0.026 Uiso 1 1 calc R . . . .
H8B H 0.530390 0.494648 0.219761 0.026 Uiso 1 1 calc R . . . .
C17 C 0.4856(3) 0.5864(2) 0.51024(18) 0.0218(6) Uani 1 1 d . . . . .
C3 C 1.0446(3) 0.5332(2) 0.4084(2) 0.0281(6) Uani 1 1 d . . . . .
H3 H 1.119255 0.534736 0.444074 0.034 Uiso 1 1 calc R . . . .
C19 C 0.2960(3) 0.5372(2) 0.59496(18) 0.0253(6) Uani 1 1 d . . . . .
H19 H 0.227753 0.490365 0.605414 0.030 Uiso 1 1 calc R . . . .
C12 C 0.4673(3) 0.6830(2) 0.14367(19) 0.0260(6) Uani 1 1 d . . . . .
H12 H 0.551558 0.658521 0.144280 0.031 Uiso 1 1 calc R . . . .
C15 C 0.2172(3) 0.7590(2) 0.1402(2) 0.0303(7) Uani 1 1 d . . . . .
H15 H 0.133273 0.784252 0.139338 0.036 Uiso 1 1 calc R . . . .
C20 C 0.3103(3) 0.6290(2) 0.64984(19) 0.0246(6) Uani 1 1 d . . . . .
C18 C 0.3839(3) 0.5156(2) 0.52446(18) 0.0240(6) Uani 1 1 d . . . . .
H18 H 0.375018 0.454422 0.487010 0.029 Uiso 1 1 calc R . . . .
C13 C 0.4117(3) 0.7132(2) 0.0589(2) 0.0293(7) Uani 1 1 d . . . . .
H13 H 0.458308 0.708378 0.003366 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2853(3) 0.7509(2) 0.0573(2) 0.0317(7) Uani 1 1 d . . . . .
H14 H 0.247335 0.770467 0.000563 0.038 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
Cl1 C20 1.742(3) . ?
O1 C7 1.235(3) . ?
N1 C7 1.380(4) . ?
N1 C9 1.419(3) . ?
N1 C17 1.453(3) . ?
N2 C6 1.362(3) . ?
N2 C8 1.443(3) . ?
C10 C11 1.470(4) . ?
C10 C9 1.341(4) . ?
C5 C6 1.416(4) . ?
C5 C4 1.372(4) . ?
C11 C16 1.405(4) . ?
C11 C12 1.400(4) . ?
C7 C1 1.496(4) . ?
C22 C21 1.383(4) . ?
C22 C17 1.387(4) . ?
C1 C6 1.419(4) . ?
C1 C2 1.411(4) . ?
C9 C8 1.504(4) . ?
C4 C3 1.397(4) . ?
C21 C20 1.385(4) . ?
C16 C15 1.386(4) . ?
C2 C3 1.373(4) . ?
C17 C18 1.391(4) . ?
C19 C20 1.386(4) . ?
C19 C18 1.385(4) . ?
C12 C13 1.388(4) . ?
C15 C14 1.380(5) . ?
C13 C14 1.399(5) . ?

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
C7 N1 C9 126.4(2) . . ?
C7 N1 C17 115.6(2) . . ?
C9 N1 C17 118.0(2) . . ?
C6 N2 C8 122.6(2) . . ?
C9 C10 C11 128.0(2) . . ?
C4 C5 C6 121.6(3) . . ?
C16 C11 C10 118.4(2) . . ?
C12 C11 C10 123.8(3) . . ?
C12 C11 C16 117.8(3) . . ?
O1 C7 N1 117.8(3) . . ?
O1 C7 C1 119.3(3) . . ?
N1 C7 C1 122.7(2) . . ?
C21 C22 C17 120.0(3) . . ?
C6 C1 C7 130.0(3) . . ?
C2 C1 C7 112.5(2) . . ?
C2 C1 C6 117.5(3) . . ?
N2 C6 C5 116.0(2) . . ?
N2 C6 C1 125.3(3) . . ?
C5 C6 C1 118.6(3) . . ?
N1 C9 C8 113.6(2) . . ?
C10 C9 N1 120.3(2) . . ?
C10 C9 C8 126.0(2) . . ?
C5 C4 C3 120.5(3) . . ?
C22 C21 C20 119.1(3) . . ?
C15 C16 C11 121.1(3) . . ?
C3 C2 C1 123.3(2) . . ?
N2 C8 C9 112.8(2) . . ?
C22 C17 N1 119.4(2) . . ?
C22 C17 C18 120.7(3) . . ?
C18 C17 N1 119.9(2) . . ?
C2 C3 C4 118.6(3) . . ?
C18 C19 C20 119.6(3) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C15 C16 120.3(3) . . ?
C21 C20 Cl1 119.2(2) . . ?
C21 C20 C19 121.3(3) . . ?
C19 C20 Cl1 119.5(2) . . ?
C19 C18 C17 119.3(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 119.6(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_gpg_2_sophf_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2062376'
loop_
_audit_author_name
_audit_author_address
'SANDIP KUNDU'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 O3 S'
_chemical_formula_sum            'C24 H22 N2 O3 S'
_chemical_formula_weight         418.49
_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                   8.130(3)
_cell_length_b                   10.804(6)
_cell_length_c                   12.330(5)
_cell_angle_alpha                82.36(2)
_cell_angle_beta                 88.815(12)
_cell_angle_gamma                80.34(2)
_cell_volume                     1058.1(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    273
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0819 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.9221. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_preparation       'pet ether'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.243
_diffrn_reflns_theta_min         2.378
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                3683
_reflns_number_total             4724
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.077
_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)+(0.0655P)²+0.2605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1318
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C1(H1), C4(H4), C23(H23), C14(H14), C19(H19), C22(H22), C3(H3),
 C2(H2), C11(H11), C12(H12), C13(H13), C20(H20)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.70517(6) 0.29433(5) 0.11175(4) 0.05011(16) Uani 1 1 d . . . . .
O1 O 0.25616(15) 0.21109(12) 0.34262(11) 0.0500(3) Uani 1 1 d . . . . .
N2 N 0.31163(15) 0.40857(12) 0.28625(11) 0.0363(3) Uani 1 1 d . . . . .
N3 N 0.65990(17) 0.36262(13) 0.22239(12) 0.0404(3) Uani 1 1 d . . . . .
O2 O 0.86602(17) 0.21704(16) 0.12665(13) 0.0692(4) Uani 1 1 d . . . . .
O3 O 0.6773(2) 0.39357(15) 0.02086(11) 0.0704(4) Uani 1 1 d . . . . .
C6 C 0.52856(19) 0.24668(14) 0.37937(12) 0.0339(3) Uani 1 1 d . . . . .
C9 C 0.03787(18) 0.55303(15) 0.25247(13) 0.0363(3) Uani 1 1 d . . . . .
C7 C 0.35358(19) 0.28650(14) 0.33425(12) 0.0344(3) Uani 1 1 d . . . . .
C5 C 0.67145(19) 0.28226(14) 0.32598(13) 0.0370(3) Uani 1 1 d . . . . .
C8 C 0.1622(2) 0.44692(16) 0.21556(13) 0.0392(4) Uani 1 1 d . . . . .
H8A H 0.107565 0.374016 0.213669 0.047 Uiso 1 1 calc R . . . .
H8B H 0.197352 0.473219 0.141626 0.047 Uiso 1 1 calc R . . . .
C15 C 0.4216(2) 0.49869(14) 0.29324(14) 0.0394(4) Uani 1 1 d . . . . .
C17 C 0.5638(2) 0.49243(15) 0.21390(15) 0.0439(4) Uani 1 1 d . . . . .
H17A H 0.520930 0.518010 0.140035 0.053 Uiso 1 1 calc R . . . .
H17B H 0.636559 0.550673 0.228901 0.053 Uiso 1 1 calc R . . . .
C10 C -0.0366(2) 0.54227(18) 0.35461(14) 0.0492(4) Uani 1 1 d . . . . .
H10 H -0.012879 0.466621 0.401451 0.059 Uiso 1 1 calc R . . . .
C18 C 0.5584(2) 0.19289(17) 0.10764(14) 0.0449(4) Uani 1 1 d . . . . .
C1 C 0.5487(2) 0.16102(16) 0.47477(14) 0.0444(4) Uani 1 1 d . . . . .
H1 H 0.455142 0.135261 0.509535 0.053 Uiso 1 1 calc R . . . .
C4 C 0.8282(2) 0.23349(17) 0.37104(17) 0.0504(4) Uani 1 1 d . . . . .
H4 H 0.922971 0.256767 0.336058 0.060 Uiso 1 1 calc R . . . .
C23 C 0.4025(2) 0.23864(19) 0.06039(15) 0.0518(5) Uani 1 1 d . . . . .
H23 H 0.378943 0.320685 0.023948 0.062 Uiso 1 1 calc R . . . .
C14 C -0.0066(3) 0.66345(18) 0.18251(16) 0.0554(5) Uani 1 1 d . . . . .
H14 H 0.038751 0.671083 0.112539 0.066 Uiso 1 1 calc R . . . .
C19 C 0.5936(2) 0.07027(18) 0.16038(18) 0.0560(5) Uani 1 1 d . . . . .
H19 H 0.697646 0.039544 0.192224 0.067 Uiso 1 1 calc R . . . .
C22 C 0.2837(3) 0.1611(2) 0.06820(17) 0.0588(5) Uani 1 1 d . . . . .
H22 H 0.178937 0.192109 0.037416 0.071 Uiso 1 1 calc R . . . .
C3 C 0.8443(3) 0.15103(18) 0.46699(18) 0.0589(5) Uani 1 1 d . . . . .
H3 H 0.949664 0.120512 0.496954 0.071 Uiso 1 1 calc R . . . .
C2 C 0.7057(3) 0.11323(18) 0.51909(16) 0.0558(5) Uani 1 1 d . . . . .
H2 H 0.717372 0.056399 0.583177 0.067 Uiso 1 1 calc R . . . .
C11 C -0.1460(2) 0.6429(2) 0.38779(15) 0.0568(5) Uani 1 1 d . . . . .
H11 H -0.193121 0.635378 0.457228 0.068 Uiso 1 1 calc R . . . .
C25 C 0.3942(3) 0.5811(2) 0.3633(2) 0.0613(6) Uani 1 1 d . . . . .
C12 C -0.1847(3) 0.7538(2) 0.31812(17) 0.0583(5) Uani 1 1 d . . . . .
H12 H -0.256053 0.822241 0.340708 0.070 Uiso 1 1 calc R . . . .
C21 C 0.3160(3) 0.0379(2) 0.12081(18) 0.0585(5) Uani 1 1 d . . . . .
C13 C -0.1176(3) 0.7631(2) 0.21489(19) 0.0679(6) Uani 1 1 d . . . . .
H13 H -0.147055 0.836893 0.166480 0.082 Uiso 1 1 calc R . . . .
C20 C 0.4732(3) -0.0059(2) 0.1653(2) 0.0627(5) Uani 1 1 d . . . . .
H20 H 0.498024 -0.088968 0.199430 0.075 Uiso 1 1 calc R . . . .
C24 C 0.1838(3) -0.0445(3) 0.1312(3) 0.0888(8) Uani 1 1 d . . . . .
H24A H 0.097391 -0.011997 0.179166 0.133 Uiso 1 1 calc GR . . . .
H24B H 0.232161 -0.129263 0.160753 0.133 Uiso 1 1 calc GR . . . .
H24C H 0.137207 -0.045130 0.060419 0.133 Uiso 1 1 calc GR . . . .
H25A H 0.299(3) 0.585(2) 0.411(2) 0.076(7) Uiso 1 1 d . . . . .
H25B H 0.467(3) 0.638(2) 0.3656(18) 0.066(6) 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
S1 N3 1.6421(16) . ?
S1 O2 1.4296(15) . ?
S1 O3 1.4374(16) . ?
S1 C18 1.756(2) . ?
O1 C7 1.2216(19) . ?
N2 C7 1.362(2) . ?
N2 C8 1.478(2) . ?
N2 C15 1.439(2) . ?
N3 C5 1.441(2) . ?
N3 C17 1.478(2) . ?
C6 C7 1.511(2) . ?
C6 C5 1.408(2) . ?
C6 C1 1.391(2) . ?
C9 C8 1.508(2) . ?
C9 C10 1.385(2) . ?
C9 C14 1.376(2) . ?
C5 C4 1.392(2) . ?
C15 C17 1.497(2) . ?
C15 C25 1.311(3) . ?
C10 C11 1.386(3) . ?
C18 C23 1.391(3) . ?
C18 C19 1.382(3) . ?
C1 C2 1.389(3) . ?
C4 C3 1.377(3) . ?
C23 C22 1.375(3) . ?
C14 C13 1.381(3) . ?
C19 C20 1.376(3) . ?
C22 C21 1.386(3) . ?
C3 C2 1.380(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.372(3) . ?
C21 C20 1.384(3) . ?
C21 C24 1.500(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 S1 C18 105.19(8) . . ?
O2 S1 N3 108.15(9) . . ?
O2 S1 O3 119.46(9) . . ?
O2 S1 C18 107.50(10) . . ?
O3 S1 N3 106.29(9) . . ?
O3 S1 C18 109.38(10) . . ?
C7 N2 C8 120.41(13) . . ?
C7 N2 C15 120.57(13) . . ?
C15 N2 C8 118.64(13) . . ?
C5 N3 S1 117.52(11) . . ?
C5 N3 C17 119.82(14) . . ?
C17 N3 S1 120.15(12) . . ?
C5 C6 C7 123.99(14) . . ?
C1 C6 C7 116.98(14) . . ?
C1 C6 C5 118.79(15) . . ?
C10 C9 C8 122.03(15) . . ?
C14 C9 C8 119.57(15) . . ?
C14 C9 C10 118.38(16) . . ?
O1 C7 N2 122.86(15) . . ?
O1 C7 C6 120.20(14) . . ?
N2 C7 C6 116.94(13) . . ?
C6 C5 N3 121.44(14) . . ?
C4 C5 N3 119.05(15) . . ?
C4 C5 C6 119.42(16) . . ?
N2 C8 C9 113.84(13) . . ?
N2 C15 C17 115.22(14) . . ?
C25 C15 N2 121.19(17) . . ?
C25 C15 C17 123.58(18) . . ?
N3 C17 C15 110.73(13) . . ?
C9 C10 C11 120.75(17) . . ?
C23 C18 S1 120.28(15) . . ?
C19 C18 S1 119.31(14) . . ?
C19 C18 C23 120.16(19) . . ?
C2 C1 C6 121.24(17) . . ?
C3 C4 C5 120.58(18) . . ?
C22 C23 C18 119.20(19) . . ?
C9 C14 C13 120.81(18) . . ?
C20 C19 C18 119.38(18) . . ?
C23 C22 C21 121.65(18) . . ?
C4 C3 C2 120.69(17) . . ?
C3 C2 C1 119.25(17) . . ?
C12 C11 C10 119.95(17) . . ?
C11 C12 C13 119.61(18) . . ?
C22 C21 C24 121.1(2) . . ?
C20 C21 C22 117.9(2) . . ?
C20 C21 C24 121.0(2) . . ?
C12 C13 C14 120.38(18) . . ?
C19 C20 C21 121.6(2) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 8.9 0.2 ?

_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_dm_3_5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2062377'
loop_
_audit_author_name
_audit_author_address
'SANDIP KUNDU'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.4643(6)
_cell_length_b                   18.1630(12)
_cell_length_c                   10.9267(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.234(2)
_cell_angle_gamma                90
_cell_volume                     1725.97(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      63.53
_cell_measurement_theta_min      5.03
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.496
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.7160.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark grey'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18502
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        63.525
_diffrn_reflns_theta_max         63.525
_diffrn_reflns_theta_min         5.033
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2653
_reflns_number_total             2684
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0153(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.093
_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)+(0.0437P)²+1.3266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1010
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C1A(H1A), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.35466(5) 0.37679(2) 0.96551(4) 0.01797(19) Uani 1 1 d . . . . .
O1 O 0.47896(15) 0.39146(7) 1.09041(12) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.22640(15) 0.42629(7) 0.92001(13) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.42591(17) 0.37520(8) 0.85059(15) 0.0177(4) Uani 1 1 d . . . . .
N2 N 0.20714(18) 0.25963(9) 0.73219(15) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.210378 0.224802 0.677366 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3180(2) 0.37956(10) 0.71304(18) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.3584(2) 0.41994(10) 0.63007(18) 0.0189(4) Uani 1 1 d . . . . .
H3 H 0.458473 0.440898 0.666808 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2108(2) 0.16470(11) 0.88442(19) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.174073 0.131482 0.811403 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2345(2) 0.23897(10) 0.86088(18) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.1732(2) 0.33444(10) 0.67858(18) 0.0200(4) Uani 1 1 d . . . . .
H6A H 0.104650 0.358872 0.715041 0.024 Uiso 1 1 calc R U . . .
H6B H 0.118333 0.332021 0.580549 0.024 Uiso 1 1 calc R U . . .
C1 C 0.2940(2) 0.28540(10) 0.97330(18) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.2616(2) 0.46751(11) 0.27106(19) 0.0246(5) Uani 1 1 d . . . . .
H7 H 0.314191 0.473738 0.213493 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2394(2) 0.13900(11) 1.01023(19) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.224136 0.088340 1.022871 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2672(2) 0.43602(10) 0.48868(18) 0.0185(4) Uani 1 1 d . . . . .
C10 C 0.5747(2) 0.33998(10) 0.88439(17) 0.0178(4) Uani 1 1 d . . . . .
C11 C 0.3425(2) 0.44649(10) 0.40228(19) 0.0206(4) Uani 1 1 d . . . . .
H11 H 0.450468 0.439070 0.434114 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2905(2) 0.18623(11) 1.11948(19) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.305245 0.168740 1.205613 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1079(2) 0.44634(10) 0.43776(19) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.053953 0.438216 0.493717 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7078(2) 0.37638(11) 0.96645(19) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.702694 0.424728 0.997651 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1044(2) 0.47948(11) 0.22347(19) 0.0272(5) Uani 1 1 d . . . . .
H15 H 0.049631 0.495271 0.134260 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5820(2) 0.27026(10) 0.83548(19) 0.0211(4) Uani 1 1 d . . . . .
H16 H 0.490775 0.246207 0.778141 0.025 Uiso 1 1 calc R U . . .
C17 C 0.3191(2) 0.25860(11) 1.10047(19) 0.0205(4) Uani 1 1 d . . . . .
H17 H 0.356479 0.290971 1.174711 0.025 Uiso 1 1 calc R U . . .
C18 C 0.0273(2) 0.46828(11) 0.3068(2) 0.0254(5) Uani 1 1 d . . . . .
H18 H -0.080706 0.475632 0.274153 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7232(2) 0.23592(11) 0.8707(2) 0.0257(5) Uani 1 1 d . . . . .
H19 H 0.728780 0.188274 0.837039 0.031 Uiso 1 1 calc R U . . .
C1A C 0.8567(2) 0.27072(13) 0.9550(2) 0.0308(5) Uani 1 1 d . . . . .
H1A H 0.953121 0.246622 0.980305 0.037 Uiso 1 1 calc R U . . .
C20 C 0.8487(2) 0.34057(13) 1.0020(2) 0.0308(5) Uani 1 1 d . . . . .
H20 H 0.940278 0.364465 1.059177 0.037 Uiso 1 1 calc R U . . .


_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 1.4320(14) . ?
S1 O2 1.4327(13) . ?
S1 N1 1.6432(16) . ?
S1 C1 1.7695(19) . ?
N1 C2 1.448(2) . ?
N1 C10 1.455(2) . ?
N2 H2 0.8800 . ?
N2 C5 1.378(2) . ?
N2 C6 1.464(2) . ?
C2 C3 1.334(3) . ?
C2 C6 1.512(3) . ?
C3 H3 0.9500 . ?
C3 C9 1.471(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.408(3) . ?
C4 C8 1.374(3) . ?
C5 C1 1.411(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 C17 1.401(3) . ?
C7 H7 0.9500 . ?
C7 C11 1.386(3) . ?
C7 C15 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C12 1.393(3) . ?
C9 C11 1.402(3) . ?
C9 C13 1.399(3) . ?
C10 C14 1.392(3) . ?
C10 C16 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C17 1.374(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C20 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C18 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C19 1.385(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C1A 1.387(3) . ?
C1A H1A 0.9500 . ?
C1A C20 1.382(3) . ?
C20 H20 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 O2 118.62(8) . . ?
O1 S1 N1 107.52(8) . . ?
O1 S1 C1 106.79(8) . . ?
O2 S1 N1 107.03(8) . . ?
O2 S1 C1 111.03(8) . . ?
N1 S1 C1 105.01(8) . . ?
C2 N1 S1 117.28(12) . . ?
C2 N1 C10 120.19(14) . . ?
C10 N1 S1 117.47(12) . . ?
C5 N2 H2 117.1 . . ?
C5 N2 C6 125.75(15) . . ?
C6 N2 H2 117.1 . . ?
N1 C2 C6 115.32(15) . . ?
C3 C2 N1 117.49(16) . . ?
C3 C2 C6 127.14(17) . . ?
C2 C3 H3 116.0 . . ?
C2 C3 C9 128.02(18) . . ?
C9 C3 H3 116.0 . . ?
C5 C4 H4 119.1 . . ?
C8 C4 H4 119.1 . . ?
C8 C4 C5 121.71(18) . . ?
N2 C5 C4 117.92(17) . . ?
N2 C5 C1 125.13(17) . . ?
C4 C5 C1 116.82(17) . . ?
N2 C6 C2 111.65(15) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C2 C6 H6A 109.3 . . ?
C2 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C5 C1 S1 122.98(14) . . ?
C17 C1 S1 116.25(14) . . ?
C17 C1 C5 120.59(17) . . ?
C11 C7 H7 119.9 . . ?
C11 C7 C15 120.27(18) . . ?
C15 C7 H7 119.9 . . ?
C4 C8 H8 119.6 . . ?
C4 C8 C12 120.88(18) . . ?
C12 C8 H8 119.6 . . ?
C11 C9 C3 119.36(17) . . ?
C13 C9 C3 122.56(17) . . ?
C13 C9 C11 117.94(17) . . ?
C14 C10 N1 119.59(16) . . ?
C16 C10 N1 119.63(16) . . ?
C16 C10 C14 120.77(17) . . ?
C7 C11 C9 120.92(18) . . ?
C7 C11 H11 119.5 . . ?
C9 C11 H11 119.5 . . ?
C8 C12 H12 120.6 . . ?
C17 C12 C8 118.82(18) . . ?
C17 C12 H12 120.6 . . ?
C9 C13 H13 119.5 . . ?
C18 C13 C9 121.07(18) . . ?
C18 C13 H13 119.5 . . ?
C10 C14 H14 120.6 . . ?
C10 C14 C20 118.77(19) . . ?
C20 C14 H14 120.6 . . ?
C7 C15 H15 120.2 . . ?
C7 C15 C18 119.69(18) . . ?
C18 C15 H15 120.2 . . ?
C10 C16 H16 120.2 . . ?
C19 C16 C10 119.60(18) . . ?
C19 C16 H16 120.2 . . ?
C1 C17 H17 119.5 . . ?
C12 C17 C1 121.04(18) . . ?
C12 C17 H17 119.5 . . ?
C13 C18 H18 120.0 . . ?
C15 C18 C13 120.07(19) . . ?
C15 C18 H18 120.0 . . ?
C16 C19 H19 119.8 . . ?
C16 C19 C1A 120.35(19) . . ?
C1A C19 H19 119.8 . . ?
C19 C1A H1A 120.1 . . ?
C20 C1A C19 119.76(19) . . ?
C20 C1A H1A 120.1 . . ?
C14 C20 H20 119.6 . . ?
C1A C20 C14 120.7(2) . . ?
C1A C20 H20 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C2 C3 140.94(15) . . . . ?
S1 N1 C2 C6 -41.55(19) . . . . ?
S1 N1 C10 C14 -75.86(19) . . . . ?
S1 N1 C10 C16 103.55(17) . . . . ?
S1 C1 C17 C12 -173.53(14) . . . . ?
O1 S1 N1 C2 -165.02(12) . . . . ?
O1 S1 N1 C10 40.04(15) . . . . ?
O1 S1 C1 C5 -147.76(15) . . . . ?
O1 S1 C1 C17 27.42(16) . . . . ?
O2 S1 N1 C2 -36.56(14) . . . . ?
O2 S1 N1 C10 168.50(13) . . . . ?
O2 S1 C1 C5 81.55(16) . . . . ?
O2 S1 C1 C17 -103.27(15) . . . . ?
N1 S1 C1 C5 -33.78(17) . . . . ?
N1 S1 C1 C17 141.40(14) . . . . ?
N1 C2 C3 C9 -176.70(16) . . . . ?
N1 C2 C6 N2 -46.6(2) . . . . ?
N1 C10 C14 C20 177.50(16) . . . . ?
N1 C10 C16 C19 -178.18(16) . . . . ?
N2 C5 C1 S1 -4.3(3) . . . . ?
N2 C5 C1 C17 -179.33(17) . . . . ?
C2 N1 C10 C14 129.96(18) . . . . ?
C2 N1 C10 C16 -50.6(2) . . . . ?
C2 C3 C9 C11 -148.95(19) . . . . ?
C2 C3 C9 C13 35.5(3) . . . . ?
C3 C2 C6 N2 130.64(19) . . . . ?
C3 C9 C11 C7 -174.79(17) . . . . ?
C3 C9 C13 C18 173.83(17) . . . . ?
C4 C5 C1 S1 171.44(14) . . . . ?
C4 C5 C1 C17 -3.5(3) . . . . ?
C4 C8 C12 C17 -3.1(3) . . . . ?
C5 N2 C6 C2 81.7(2) . . . . ?
C5 C4 C8 C12 1.3(3) . . . . ?
C5 C1 C17 C12 1.8(3) . . . . ?
C6 N2 C5 C4 157.61(17) . . . . ?
C6 N2 C5 C1 -26.6(3) . . . . ?
C6 C2 C3 C9 6.1(3) . . . . ?
C1 S1 N1 C2 81.51(14) . . . . ?
C1 S1 N1 C10 -73.43(14) . . . . ?
C7 C15 C18 C13 1.0(3) . . . . ?
C8 C4 C5 N2 178.16(17) . . . . ?
C8 C4 C5 C1 2.1(3) . . . . ?
C8 C12 C17 C1 1.6(3) . . . . ?
C9 C13 C18 C15 0.8(3) . . . . ?
C10 N1 C2 C3 -64.8(2) . . . . ?
C10 N1 C2 C6 112.68(18) . . . . ?
C10 C14 C20 C1A 1.1(3) . . . . ?
C10 C16 C19 C1A 0.3(3) . . . . ?
C11 C7 C15 C18 -1.8(3) . . . . ?
C11 C9 C13 C18 -1.8(3) . . . . ?
C13 C9 C11 C7 1.0(3) . . . . ?
C14 C10 C16 C19 1.2(3) . . . . ?
C15 C7 C11 C9 0.8(3) . . . . ?
C16 C10 C14 C20 -1.9(3) . . . . ?
C16 C19 C1A C20 -1.2(3) . . . . ?
C19 C1A C20 C14 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# 
_vrf_PLAT029_dm_3_5_0m_a         
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.951 Why?
RESPONSE: This alert arises due to weakly diffracting nature of the crystal 
at higher Bragg angle.
;
# 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_gpg_2_15_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2062378'
loop_
_audit_author_name
_audit_author_address
'SANDIP KUNDU'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2021-01-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C22 H20 N2 O4 S2)'
_chemical_formula_sum            'C11 H10 N O2 S'
_chemical_formula_weight         220.26
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   15.9293(11)
_cell_length_b                   8.0486(5)
_cell_length_c                   16.3016(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.033(4)
_cell_angle_gamma                90
_cell_volume                     2036.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    273
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.551
_exptl_absorpt_coefficient_mu    2.651
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0819 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.9221. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull dark white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_preparation       'Pet ether in DCM'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            58258
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.883
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3591
_reflns_number_total             3606
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.274
_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)+6.6871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1410
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H11 of C11, H21 of C21, H10 of C10, H2 of C2, H13 of C13,
   H17 of C17, H5 of C5, H18 of C18, H12 of C12, H4 of C4, H3 of C3, H20 of C20,
   H14 of C14
 At 1.5 times of:
  All C(H,H,H) groups, H15A of C15
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C2(H2), C10(H10), C21(H21), C11(H11), C17(H17), C5(H5),
 C18(H18), C12(H12), C4(H4), C3(H3), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 C15(H15A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.31305(6) 0.13521(11) 0.54043(6) 0.0203(3) Uani 1 1 d . . . . .
S2 S 0.17745(6) 0.49034(11) 0.39541(6) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.26401(16) 0.1121(3) 0.45518(16) 0.0240(6) Uani 1 1 d . . . . .
O3 O 0.21906(18) 0.5205(3) 0.32678(16) 0.0282(6) Uani 1 1 d . . . . .
O1 O 0.33888(17) -0.0046(3) 0.59516(18) 0.0269(6) Uani 1 1 d . . . . .
O4 O 0.12593(17) 0.3469(3) 0.39502(18) 0.0290(7) Uani 1 1 d . . . . .
N2 N 0.25352(19) 0.4871(4) 0.48338(19) 0.0207(7) Uani 1 1 d . . . . .
N1 N 0.39854(19) 0.2315(4) 0.52973(19) 0.0200(7) Uani 1 1 d . . . . .
C6 C 0.2362(2) 0.4336(5) 0.5636(2) 0.0194(8) Uani 1 1 d . . . . .
C9 C 0.4700(2) 0.2394(4) 0.6039(2) 0.0207(8) Uani 1 1 d . . . . .
C16 C 0.1120(2) 0.6619(4) 0.4024(2) 0.0209(8) Uani 1 1 d . . . . .
C1 C 0.2612(2) 0.2753(5) 0.5977(2) 0.0206(8) Uani 1 1 d . . . . .
C14 C 0.4668(2) 0.3322(5) 0.6766(2) 0.0249(8) Uani 1 1 d . . . . .
H14 H 0.417268 0.391824 0.678399 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3428(2) 0.5168(4) 0.4795(2) 0.0227(8) Uani 1 1 d . . . . .
H7A H 0.372943 0.567128 0.532013 0.027 Uiso 1 1 calc R . . . .
H7B H 0.343984 0.595073 0.434568 0.027 Uiso 1 1 calc R . . . .
C8 C 0.3891(2) 0.3618(5) 0.4648(2) 0.0226(8) Uani 1 1 d . . . . .
C13 C 0.5368(3) 0.3359(5) 0.7458(2) 0.0269(9) Uani 1 1 d . . . . .
H13 H 0.534591 0.398369 0.793242 0.032 Uiso 1 1 calc R . . . .
C2 C 0.2500(2) 0.2321(5) 0.6787(2) 0.0265(9) Uani 1 1 d . . . . .
H2 H 0.267936 0.128407 0.701123 0.032 Uiso 1 1 calc R . . . .
C19 C 0.0007(3) 0.9282(5) 0.3913(3) 0.0258(9) Uani 1 1 d . . . . .
C10 C 0.5416(2) 0.1499(5) 0.6001(3) 0.0243(8) Uani 1 1 d . . . . .
H10 H 0.544164 0.088280 0.552477 0.029 Uiso 1 1 calc R . . . .
C21 C 0.0313(3) 0.6357(5) 0.4135(3) 0.0283(9) Uani 1 1 d . . . . .
H21 H 0.013220 0.529404 0.423928 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6109(2) 0.1534(5) 0.6696(3) 0.0261(9) Uani 1 1 d . . . . .
H11 H 0.660187 0.092798 0.667934 0.031 Uiso 1 1 calc R . . . .
C17 C 0.1394(2) 0.8211(5) 0.3896(2) 0.0237(8) Uani 1 1 d . . . . .
H17 H 0.195988 0.839095 0.385491 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1983(2) 0.5428(5) 0.6098(2) 0.0257(9) Uani 1 1 d . . . . .
H5 H 0.180387 0.646816 0.587854 0.031 Uiso 1 1 calc R . . . .
C18 C 0.0832(3) 0.9528(5) 0.3831(3) 0.0274(9) Uani 1 1 d . . . . .
H18 H 0.101465 1.059003 0.372995 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6085(2) 0.2459(5) 0.7424(2) 0.0257(9) Uani 1 1 d . . . . .
H12 H 0.655735 0.245732 0.787942 0.031 Uiso 1 1 calc R . . . .
C15 C 0.4203(3) 0.3367(5) 0.3963(3) 0.0310(9) Uani 1 1 d . . . . .
H15A H 0.444176 0.245932 0.399588 0.046 Uiso 1 1 calc GR . . . .
C4 C 0.1866(3) 0.4973(5) 0.6905(3) 0.0288(9) Uani 1 1 d . . . . .
H4 H 0.161005 0.572300 0.720749 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2124(2) 0.3431(5) 0.7251(2) 0.0282(9) Uani 1 1 d . . . . .
H3 H 0.204829 0.314610 0.778227 0.034 Uiso 1 1 calc R . . . .
C20 C -0.0234(3) 0.7691(5) 0.4092(3) 0.0290(9) Uani 1 1 d . . . . .
H20 H -0.078189 0.752135 0.418620 0.035 Uiso 1 1 calc R . . . .
C22 C -0.0610(3) 1.0700(5) 0.3795(3) 0.0363(10) Uani 1 1 d . . . . .
H22A H -0.029610 1.172702 0.384523 0.054 Uiso 1 1 calc GR . . . .
H22B H -0.094263 1.065401 0.421785 0.054 Uiso 1 1 calc GR . . . .
H22C H -0.098776 1.063119 0.324727 0.054 Uiso 1 1 calc GR . . . .
H15B H 0.414(3) 0.422(6) 0.355(3) 0.033(12) 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
S1 O2 1.445(3) . ?
S1 O1 1.437(3) . ?
S1 N1 1.610(3) . ?
S1 C1 1.781(4) . ?
S2 O3 1.444(3) . ?
S2 O4 1.416(3) . ?
S2 N2 1.656(3) . ?
S2 C16 1.749(4) . ?
N2 C6 1.461(5) . ?
N2 C7 1.457(5) . ?
N1 C9 1.463(5) . ?
N1 C8 1.474(5) . ?
C6 C1 1.411(5) . ?
C6 C5 1.382(5) . ?
C9 C14 1.411(5) . ?
C9 C10 1.362(5) . ?
C16 C21 1.355(5) . ?
C16 C17 1.384(5) . ?
C1 C2 1.415(5) . ?
C14 C13 1.397(6) . ?
C7 C8 1.497(5) . ?
C8 C15 1.337(6) . ?
C13 C12 1.364(6) . ?
C2 C3 1.390(6) . ?
C19 C18 1.365(6) . ?
C19 C20 1.387(6) . ?
C19 C22 1.489(5) . ?
C10 C11 1.392(6) . ?
C21 C20 1.374(6) . ?
C11 C12 1.408(6) . ?
C17 C18 1.376(5) . ?
C5 C4 1.417(6) . ?
C4 C3 1.387(6) . ?

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 N1 104.18(16) . . ?
O2 S1 C1 111.82(16) . . ?
O1 S1 O2 120.88(16) . . ?
O1 S1 N1 108.25(16) . . ?
O1 S1 C1 105.78(17) . . ?
N1 S1 C1 104.81(16) . . ?
O3 S2 N2 107.43(16) . . ?
O3 S2 C16 107.56(17) . . ?
O4 S2 O3 120.05(18) . . ?
O4 S2 N2 107.54(16) . . ?
O4 S2 C16 106.91(17) . . ?
N2 S2 C16 106.67(17) . . ?
C6 N2 S2 122.1(2) . . ?
C7 N2 S2 119.4(2) . . ?
C7 N2 C6 118.0(3) . . ?
C9 N1 S1 116.8(2) . . ?
C9 N1 C8 119.8(3) . . ?
C8 N1 S1 117.9(2) . . ?
C1 C6 N2 121.7(3) . . ?
C5 C6 N2 119.6(3) . . ?
C5 C6 C1 118.6(3) . . ?
C14 C9 N1 123.3(3) . . ?
C10 C9 N1 116.3(3) . . ?
C10 C9 C14 120.5(4) . . ?
C21 C16 S2 118.9(3) . . ?
C21 C16 C17 120.4(4) . . ?
C17 C16 S2 120.5(3) . . ?
C6 C1 S1 119.2(3) . . ?
C6 C1 C2 120.4(3) . . ?
C2 C1 S1 120.3(3) . . ?
C13 C14 C9 121.1(4) . . ?
N2 C7 C8 113.0(3) . . ?
N1 C8 C7 116.9(3) . . ?
C15 C8 N1 119.7(4) . . ?
C15 C8 C7 123.4(4) . . ?
C12 C13 C14 118.6(4) . . ?
C3 C2 C1 120.7(4) . . ?
C18 C19 C20 118.2(4) . . ?
C18 C19 C22 119.9(4) . . ?
C20 C19 C22 121.9(4) . . ?
C9 C10 C11 118.1(4) . . ?
C16 C21 C20 118.7(4) . . ?
C10 C11 C12 122.0(4) . . ?
C18 C17 C16 120.2(4) . . ?
C6 C5 C4 120.5(4) . . ?
C19 C18 C17 120.4(4) . . ?
C13 C12 C11 119.8(4) . . ?
C3 C4 C5 121.3(4) . . ?
C4 C3 C2 118.6(4) . . ?
C21 C20 C19 122.0(4) . . ?

_olex2_submission_original_sample_id GPG-3-S02
_olex2_submission_special_instructions 'No special instructions were received'
