# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_rm_5_147ab_0m_b
_database_code_depnum_ccdc_archive 'CCDC 2266370'
loop_
_audit_author_name
_audit_author_address
'Indrajit Das'
;Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 N3 O S'
_chemical_formula_sum            'C10 H9 N3 O S'
_chemical_formula_weight         219.26
_chemical_absolute_configuration rmad
_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   8.2596(7)
_cell_length_b                   11.1219(9)
_cell_length_c                   11.4922(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.896(3)
_cell_angle_gamma                90
_cell_volume                     986.27(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.36
_cell_measurement_theta_min      5.73
_shelx_estimated_absorpt_T_max   0.754
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1358 before and 0.0856 after correction.
The Ratio of minimum to maximum transmission is 0.6654.
The λ/2 correction factor is Not present.
;
_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    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19902
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.513
_diffrn_reflns_theta_min         3.975
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms Diamond'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                3084
_reflns_number_total             3260
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061
_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   0.47(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.074
_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)+(0.0596P)²+0.3586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1073
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C8(H8), N5(H5A), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_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 0.47080(17) 0.53431(14) 0.43392(12) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.8529(7) 0.1668(4) 0.6412(4) 0.0241(11) Uani 1 1 d . . . . .
O1 O 1.0017(6) 0.0016(5) 0.7339(4) 0.0266(10) Uani 1 1 d . . . . .
N2 N 0.8671(8) 0.0961(5) 0.4164(4) 0.0338(14) Uani 1 1 d . . . . .
H2 H 0.880127 0.076978 0.345915 0.041 Uiso 1 1 calc R U . . .
C2 C 0.7653(8) 0.2384(5) 0.5337(4) 0.0173(12) Uani 1 1 d . . . . .
C3 C 0.9389(10) 0.0147(6) 0.5208(6) 0.0290(14) Uani 1 1 d . . . . .
H3A H 1.060820 -0.002757 0.531272 0.035 Uiso 1 1 calc R U . . .
H3B H 0.874036 -0.062042 0.501103 0.035 Uiso 1 1 calc R U . . .
N3 N 0.7212(7) 0.7236(5) 0.4986(5) 0.0258(11) Uani 1 1 d . . . . .
C4 C 0.7829(9) 0.1977(5) 0.4191(5) 0.0233(14) Uani 1 1 d . . . . .
C5 C 0.7100(9) 0.2670(6) 0.3157(6) 0.0282(15) Uani 1 1 d . . . . .
H5 H 0.722587 0.243799 0.239781 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6152(8) 0.3738(5) 0.3186(6) 0.0261(14) Uani 1 1 d . . . . .
H6 H 0.565391 0.420755 0.245469 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5970(7) 0.4074(5) 0.4263(5) 0.0234(13) Uani 1 1 d . . . . .
C8 C 0.6738(8) 0.3379(5) 0.5373(5) 0.0210(13) Uani 1 1 d . . . . .
H8 H 0.660540 0.361649 0.612766 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6231(9) 0.6447(5) 0.4730(5) 0.0252(14) Uani 1 1 d . . . . .
C10 C 0.8540(8) 0.2145(5) 0.7614(5) 0.0215(13) Uani 1 1 d . . . . .
H10A H 0.898077 0.297111 0.772278 0.032 Uiso 1 1 calc R U . . .
H10B H 0.928850 0.164236 0.829445 0.032 Uiso 1 1 calc R U . . .
H10C H 0.735846 0.213671 0.762396 0.032 Uiso 1 1 calc R U . . .
C20 C 0.9337(8) 0.0611(5) 0.6401(6) 0.0226(13) Uani 1 1 d . . . . .
C1 C 0.0649(8) 0.4361(5) 0.3580(5) 0.0203(13) Uani 1 1 d . . . . .
S2 S 0.52711(17) -0.03441(14) 0.56597(12) 0.0303(4) Uani 1 1 d . . . . .
O2 O -0.0044(6) 0.4971(4) 0.2626(4) 0.0262(10) Uani 1 1 d . . . . .
N4 N 0.1472(6) 0.3302(4) 0.3562(4) 0.0164(10) Uani 1 1 d . . . . .
N5 N 0.1273(7) 0.4040(4) 0.5843(4) 0.0283(12) Uani 1 1 d . . . . .
H5A H 0.111288 0.421991 0.653982 0.034 Uiso 1 1 calc R U . . .
N6 N 0.2761(9) -0.2216(5) 0.5019(5) 0.0342(14) Uani 1 1 d . . . . .
C11 C 0.2279(7) 0.2653(5) 0.4687(6) 0.0219(13) Uani 1 1 d . . . . .
C12 C 0.0601(8) 0.4823(5) 0.4812(6) 0.0208(12) Uani 1 1 d . . . . .
H12A H 0.125864 0.558650 0.501351 0.025 Uiso 1 1 calc R U . . .
H12B H -0.061748 0.500886 0.470084 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2169(7) 0.3005(5) 0.5798(6) 0.0195(12) Uani 1 1 d . . . . .
C14 C 0.2923(8) 0.2272(6) 0.6885(5) 0.0237(14) Uani 1 1 d . . . . .
H14 H 0.279264 0.249533 0.764413 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3811(8) 0.1274(6) 0.6839(5) 0.0265(14) Uani 1 1 d . . . . .
H15 H 0.432520 0.080042 0.756612 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3975(8) 0.0932(5) 0.5695(5) 0.0250(13) Uani 1 1 d . . . . .
C17 C 0.3212(8) 0.1592(5) 0.4647(5) 0.0214(13) Uani 1 1 d . . . . .
H17 H 0.330375 0.134128 0.388272 0.026 Uiso 1 1 calc R U . . .
C18 C 0.3737(8) -0.1446(5) 0.5283(6) 0.0222(12) Uani 1 1 d . . . . .
C19 C 0.1459(9) 0.2850(6) 0.2363(6) 0.0277(14) Uani 1 1 d . . . . .
H19A H 0.260276 0.297252 0.230406 0.042 Uiso 1 1 calc R U . . .
H19B H 0.058379 0.328473 0.168575 0.042 Uiso 1 1 calc R U . . .
H19C H 0.118264 0.198999 0.229471 0.042 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 C7 1.775(7) . ?
S1 C9 1.700(7) . ?
N1 C2 1.430(7) . ?
N1 C10 1.477(7) . ?
N1 C20 1.354(8) . ?
O1 C20 1.218(8) . ?
N2 H2 0.8800 . ?
N2 C3 1.451(8) . ?
N2 C4 1.334(8) . ?
C2 C4 1.448(8) . ?
C2 C8 1.349(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C20 1.480(9) . ?
N3 C9 1.158(8) . ?
C4 C5 1.364(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.429(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.352(9) . ?
C7 C8 1.432(8) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1 O2 1.241(7) . ?
C1 N4 1.364(7) . ?
C1 C12 1.520(8) . ?
S2 C16 1.787(6) . ?
S2 C18 1.704(6) . ?
N4 C11 1.422(7) . ?
N4 C19 1.464(8) . ?
N5 H5A 0.8800 . ?
N5 C12 1.415(7) . ?
N5 C13 1.379(7) . ?
N6 C18 1.141(8) . ?
C11 C13 1.370(9) . ?
C11 C17 1.419(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.434(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.341(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.421(8) . ?
C16 C17 1.358(8) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C9 S1 C7 101.3(3) . . ?
C2 N1 C10 116.2(4) . . ?
C20 N1 C2 125.1(5) . . ?
C20 N1 C10 118.8(5) . . ?
C3 N2 H2 117.6 . . ?
C4 N2 H2 117.6 . . ?
C4 N2 C3 124.9(5) . . ?
N1 C2 C4 115.3(5) . . ?
C8 C2 N1 123.2(5) . . ?
C8 C2 C4 121.5(5) . . ?
N2 C3 H3A 108.7 . . ?
N2 C3 H3B 108.7 . . ?
N2 C3 C20 114.2(5) . . ?
H3A C3 H3B 107.6 . . ?
C20 C3 H3A 108.7 . . ?
C20 C3 H3B 108.7 . . ?
N2 C4 C2 120.6(5) . . ?
N2 C4 C5 122.0(6) . . ?
C5 C4 C2 117.4(5) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(6) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 S1 121.6(5) . . ?
C6 C7 C8 120.5(6) . . ?
C8 C7 S1 117.9(5) . . ?
C2 C8 C7 119.4(5) . . ?
C2 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N3 C9 S1 177.0(6) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C20 C3 119.3(6) . . ?
O1 C20 N1 122.4(6) . . ?
O1 C20 C3 118.3(6) . . ?
O2 C1 N4 122.3(5) . . ?
O2 C1 C12 118.8(5) . . ?
N4 C1 C12 119.0(5) . . ?
C18 S2 C16 100.3(3) . . ?
C1 N4 C11 120.0(5) . . ?
C1 N4 C19 118.3(5) . . ?
C11 N4 C19 121.7(5) . . ?
C12 N5 H5A 118.7 . . ?
C13 N5 H5A 118.7 . . ?
C13 N5 C12 122.6(5) . . ?
C13 C11 N4 122.5(5) . . ?
C13 C11 C17 119.0(5) . . ?
C17 C11 N4 118.5(6) . . ?
C1 C12 H12A 108.3 . . ?
C1 C12 H12B 108.3 . . ?
N5 C12 C1 116.1(4) . . ?
N5 C12 H12A 108.3 . . ?
N5 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
N5 C13 C14 121.0(5) . . ?
C11 C13 N5 119.2(6) . . ?
C11 C13 C14 119.8(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 S2 119.3(5) . . ?
C17 C16 S2 120.1(4) . . ?
C17 C16 C15 120.6(6) . . ?
C11 C17 H17 119.8 . . ?
C16 C17 C11 120.4(5) . . ?
C16 C17 H17 119.8 . . ?
N6 C18 S2 176.9(6) . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 C7 C8 C2 177.6(4) . . . . ?
N1 C2 C4 N2 3.9(9) . . . . ?
N1 C2 C4 C5 -176.3(5) . . . . ?
N1 C2 C8 C7 177.0(5) . . . . ?
N2 C3 C20 N1 5.3(9) . . . . ?
N2 C3 C20 O1 -175.3(6) . . . . ?
N2 C4 C5 C6 178.0(6) . . . . ?
C2 N1 C20 O1 -177.5(6) . . . . ?
C2 N1 C20 C3 1.9(9) . . . . ?
C2 C4 C5 C6 -1.9(9) . . . . ?
C3 N2 C4 C2 3.6(10) . . . . ?
C3 N2 C4 C5 -176.3(6) . . . . ?
C4 N2 C3 C20 -8.2(10) . . . . ?
C4 C2 C8 C7 -2.1(8) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C5 C6 C7 S1 -176.5(4) . . . . ?
C5 C6 C7 C8 0.9(9) . . . . ?
C6 C7 C8 C2 0.2(9) . . . . ?
C8 C2 C4 N2 -176.9(6) . . . . ?
C8 C2 C4 C5 2.9(9) . . . . ?
C9 S1 C7 C6 -91.8(5) . . . . ?
C9 S1 C7 C8 90.8(5) . . . . ?
C10 N1 C2 C4 173.0(5) . . . . ?
C10 N1 C2 C8 -6.2(8) . . . . ?
C10 N1 C20 O1 2.8(9) . . . . ?
C10 N1 C20 C3 -177.8(6) . . . . ?
C20 N1 C2 C4 -6.7(8) . . . . ?
C20 N1 C2 C8 174.1(6) . . . . ?
C1 N4 C11 C13 4.6(8) . . . . ?
C1 N4 C11 C17 -176.3(5) . . . . ?
S2 C16 C17 C11 -175.7(4) . . . . ?
O2 C1 N4 C11 178.5(6) . . . . ?
O2 C1 N4 C19 -2.9(8) . . . . ?
O2 C1 C12 N5 174.5(5) . . . . ?
N4 C1 C12 N5 -6.4(8) . . . . ?
N4 C11 C13 N5 -1.3(9) . . . . ?
N4 C11 C13 C14 176.3(5) . . . . ?
N4 C11 C17 C16 -178.8(5) . . . . ?
N5 C13 C14 C15 -179.2(6) . . . . ?
C11 C13 C14 C15 3.3(9) . . . . ?
C12 C1 N4 C11 -0.4(8) . . . . ?
C12 C1 N4 C19 178.1(5) . . . . ?
C12 N5 C13 C11 -6.4(9) . . . . ?
C12 N5 C13 C14 176.1(5) . . . . ?
C13 N5 C12 C1 10.0(9) . . . . ?
C13 C11 C17 C16 0.4(9) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 S2 176.1(5) . . . . ?
C14 C15 C16 C17 -1.4(9) . . . . ?
C15 C16 C17 C11 1.8(9) . . . . ?
C17 C11 C13 N5 179.6(6) . . . . ?
C17 C11 C13 C14 -2.9(8) . . . . ?
C18 S2 C16 C15 92.1(5) . . . . ?
C18 S2 C16 C17 -90.4(5) . . . . ?
C19 N4 C11 C13 -173.9(6) . . . . ?
C19 N4 C11 C17 5.3(8) . . . . ?

_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_rm_5_198aa_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2266371'
loop_
_audit_author_name
_audit_author_address
'Indrajit Das'
;Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3 O S'
_chemical_formula_sum            'C12 H11 N3 O S'
_chemical_formula_weight         245.30
_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      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                   3.9964(3)
_cell_length_b                   8.0048(5)
_cell_length_c                   17.9743(12)
_cell_angle_alpha                90.426(2)
_cell_angle_beta                 90.934(2)
_cell_angle_gamma                98.213(2)
_cell_volume                     569.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.47
_cell_measurement_theta_min      7.39
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    2.418
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1076 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.6869.
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    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16871
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        66.462
_diffrn_reflns_theta_max         66.462
_diffrn_reflns_theta_min         5.584
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_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                1849
_reflns_number_total             1852
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.070(9)
_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   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.123
_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)+(0.0255P)²+0.4450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0921
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_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 1.04892(10) 0.06996(5) 0.36395(2) 0.0177(2) Uani 1 1 d . . . . .
O1 O 0.3714(3) 0.85347(15) 0.24094(7) 0.0223(3) Uani 1 1 d . . . . .
N1 N 0.5955(3) 0.62298(17) 0.28210(7) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.7664(3) 0.56426(17) 0.13396(8) 0.0163(3) Uani 1 1 d . . . . .
N3 N 0.8431(5) 0.2074(2) 0.49895(9) 0.0321(4) Uani 1 1 d . . . . .
C1 C 0.5189(4) 0.7318(2) 0.22753(9) 0.0163(4) Uani 1 1 d . . . . .
C2 C 0.7425(4) 0.4802(2) 0.26481(9) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.6246(4) 0.6944(2) 0.15118(9) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.8236(4) 0.4532(2) 0.19027(9) 0.0153(4) Uani 1 1 d . . . . .
C5 C 0.8050(4) 0.3647(2) 0.31940(9) 0.0153(4) Uani 1 1 d . . . . .
H5 H 0.749146 0.382043 0.369769 0.018 Uiso 1 1 calc R U . . .
C6 C 0.9696(4) 0.3094(2) 0.17197(9) 0.0175(4) Uani 1 1 d . . . . .
H6 H 1.025812 0.290738 0.121735 0.021 Uiso 1 1 calc R U . . .
C7 C 0.9497(4) 0.2243(2) 0.29885(9) 0.0154(4) Uani 1 1 d . . . . .
C8 C 1.0332(4) 0.1949(2) 0.22516(9) 0.0173(4) Uani 1 1 d . . . . .
H8 H 1.131884 0.097765 0.212100 0.021 Uiso 1 1 calc R U . . .
C9 C 0.9250(4) 0.1535(2) 0.44371(10) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.5151(4) 0.6585(2) 0.35957(9) 0.0174(4) Uani 1 1 d . . . . .
H10A H 0.723933 0.676201 0.389698 0.026 Uiso 1 1 calc R U . . .
H10B H 0.362438 0.562798 0.379121 0.026 Uiso 1 1 calc R U . . .
H10C H 0.405195 0.760331 0.361559 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5605(4) 0.8199(2) 0.09287(9) 0.0189(4) Uani 1 1 d . . . . .
H11A H 0.704220 0.928588 0.104281 0.023 Uiso 1 1 calc R U . . .
H11B H 0.321643 0.839020 0.095449 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6301(5) 0.7661(2) 0.01416(10) 0.0239(4) Uani 1 1 d . . . . .
H12A H 0.594103 0.856236 -0.020392 0.036 Uiso 1 1 calc R U . . .
H12B H 0.476506 0.663198 0.000817 0.036 Uiso 1 1 calc R U . . .
H12C H 0.864546 0.744112 0.011211 0.036 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 C7 1.7887(16) . ?
S1 C9 1.6888(18) . ?
O1 C1 1.233(2) . ?
N1 C1 1.376(2) . ?
N1 C2 1.393(2) . ?
N1 C10 1.469(2) . ?
N2 C3 1.293(2) . ?
N2 C4 1.390(2) . ?
N3 C9 1.150(2) . ?
C1 C3 1.483(2) . ?
C2 C4 1.406(2) . ?
C2 C5 1.397(2) . ?
C3 C11 1.501(2) . ?
C4 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C5 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C8 1.375(2) . ?
C7 C8 1.398(2) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.517(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C9 S1 C7 100.23(8) . . ?
C1 N1 C2 121.16(14) . . ?
C1 N1 C10 118.75(13) . . ?
C2 N1 C10 120.08(13) . . ?
C3 N2 C4 118.10(14) . . ?
O1 C1 N1 122.27(15) . . ?
O1 C1 C3 121.66(15) . . ?
N1 C1 C3 116.07(14) . . ?
N1 C2 C4 118.27(15) . . ?
N1 C2 C5 121.44(14) . . ?
C5 C2 C4 120.28(15) . . ?
N2 C3 C1 123.79(15) . . ?
N2 C3 C11 120.45(15) . . ?
C1 C3 C11 115.75(14) . . ?
N2 C4 C2 122.47(15) . . ?
N2 C4 C6 118.64(15) . . ?
C6 C4 C2 118.89(15) . . ?
C2 C5 H5 120.5 . . ?
C7 C5 C2 118.90(15) . . ?
C7 C5 H5 120.5 . . ?
C4 C6 H6 119.3 . . ?
C8 C6 C4 121.44(15) . . ?
C8 C6 H6 119.3 . . ?
C5 C7 S1 122.98(13) . . ?
C5 C7 C8 121.89(15) . . ?
C8 C7 S1 115.12(12) . . ?
C6 C8 C7 118.59(15) . . ?
C6 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N3 C9 S1 178.39(16) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 108.7 . . ?
C3 C11 H11B 108.7 . . ?
C3 C11 C12 114.10(14) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 C7 C8 C6 -178.99(12) . . . . ?
O1 C1 C3 N2 -176.85(15) . . . . ?
O1 C1 C3 C11 3.7(2) . . . . ?
N1 C1 C3 N2 3.2(2) . . . . ?
N1 C1 C3 C11 -176.17(14) . . . . ?
N1 C2 C4 N2 0.8(2) . . . . ?
N1 C2 C4 C6 -179.58(14) . . . . ?
N1 C2 C5 C7 179.57(14) . . . . ?
N2 C3 C11 C12 8.0(2) . . . . ?
N2 C4 C6 C8 179.89(14) . . . . ?
C1 N1 C2 C4 2.5(2) . . . . ?
C1 N1 C2 C5 -176.66(14) . . . . ?
C1 C3 C11 C12 -172.55(14) . . . . ?
C2 N1 C1 O1 175.78(14) . . . . ?
C2 N1 C1 C3 -4.3(2) . . . . ?
C2 C4 C6 C8 0.3(2) . . . . ?
C2 C5 C7 S1 178.76(11) . . . . ?
C2 C5 C7 C8 -0.3(2) . . . . ?
C3 N2 C4 C2 -1.9(2) . . . . ?
C3 N2 C4 C6 178.46(14) . . . . ?
C4 N2 C3 C1 -0.2(2) . . . . ?
C4 N2 C3 C11 179.22(14) . . . . ?
C4 C2 C5 C7 0.4(2) . . . . ?
C4 C6 C8 C7 -0.1(2) . . . . ?
C5 C2 C4 N2 179.97(14) . . . . ?
C5 C2 C4 C6 -0.4(2) . . . . ?
C5 C7 C8 C6 0.1(2) . . . . ?
C9 S1 C7 C5 -0.97(15) . . . . ?
C9 S1 C7 C8 178.14(13) . . . . ?
C10 N1 C1 O1 -3.4(2) . . . . ?
C10 N1 C1 C3 176.54(13) . . . . ?
C10 N1 C2 C4 -178.35(14) . . . . ?
C10 N1 C2 C5 2.5(2) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_rm_5_198aa_0m_a     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.923 Why?  
RESPONSE: The crystal diffracted poorly. No reflection was removed by intention.
;
