# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AM_20_1
_database_code_depnum_ccdc_archive 'CCDC 1993595'
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-05-28 downloaded from the CCDC.
;
_audit_creation_date             2020-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C8 H7 N3 S'
_chemical_formula_sum            'C8 H7 N3 S'
_chemical_formula_weight         177.23
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.1251(14)
_cell_length_b                   7.5242(7)
_cell_length_c                   11.1940(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.098(15)
_cell_angle_gamma                90
_cell_volume                     848.55(19)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.324
_exptl_crystal_density_diffrn    1.3872
_exptl_crystal_F_000             368.5942
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4133
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.02
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1346
_reflns_number_total             1730
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3180
_refine_diff_density_min         -0.2835
_refine_diff_density_rms         0.0548
_refine_ls_d_res_high            0.8003
_refine_ls_d_res_low             10.0747
_refine_ls_goodness_of_fit_ref   1.0017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.0017
_refine_ls_shift/su_max          0.9598
_refine_ls_shift/su_mean         0.0351
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1084
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N004(H00d,H00e)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00A(H00A), C00C(H00C), C008(H008)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S001 S 0.31810(5) 0.40250(7) 0.55316(5) 0.0533(2) Uani 1.000000 .
N002 N 0.36216(17) 0.3516(2) 0.35016(16) 0.0530(5) Uani 1.000000 .
N003 N 0.42337(18) 0.2113(2) 0.43323(17) 0.0568(5) Uani 1.000000 .
C00A C 0.0798(3) 0.9072(4) 0.1904(3) 0.0883(9) Uani 1.000000 .
C00B C 0.0837(3) 0.7566(4) 0.1234(3) 0.0861(9) Uani 1.000000 .
C00C C 0.1518(3) 0.9163(3) 0.3251(3) 0.0850(9) Uani 1.000000 .
N004 N 0.4609(2) 0.1016(3) 0.64167(18) 0.0731(6) Uani 1.000000 .
C005 C 0.30393(19) 0.4621(3) 0.39722(18) 0.0458(5) Uani 1.000000 .
C006 C 0.2293(2) 0.6188(3) 0.3262(2) 0.0508(5) Uani 1.000000 .
C007 C 0.4086(2) 0.2198(3) 0.54305(19) 0.0514(5) Uani 1.000000 .
C008 C 0.2255(2) 0.7719(3) 0.3926(3) 0.0683(6) Uani 1.000000 .
C009 C 0.1574(3) 0.6132(3) 0.1901(2) 0.0683(7) Uani 1.000000 .
H009 H 0.1594(3) 0.5113(3) 0.1439(2) 0.0820(8) Uiso 1.000000 R
H00B H 0.0360(3) 0.7517(4) 0.0322(3) 0.1034(10) Uiso 1.000000 R
H00A H 0.0284(3) 1.0035(4) 0.1449(3) 0.1059(11) Uiso 1.000000 R
H00C H 0.1507(3) 1.0195(3) 0.3704(3) 0.1020(10) Uiso 1.000000 R
H008 H 0.2732(2) 0.7775(3) 0.4837(3) 0.0819(8) Uiso 1.000000 R
H00d H 0.4137(11) 0.0972(19) 0.6856(12) 0.0877(7) Uiso 1.000000 GR
H00e H 0.4604(18) -0.0006(6) 0.6071(2) 0.0877(7) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C005 1.7433(19) . ?
S001 C007 1.736(2) . ?
N002 N003 1.380(2) . ?
N002 C005 1.295(3) . ?
N003 C007 1.309(2) . ?
C00A C00B 1.370(4) . ?
C00A C00C 1.377(4) . ?
C00A H00A 0.9300 . ?
C00B C009 1.369(3) . ?
C00B H00B 0.9300 . ?
C00C C008 1.378(3) . ?
C00C H00C 0.9300 . ?
N004 C007 1.343(3) . ?
N004 H00d 0.8600 . ?
N004 H00e 0.8600 . ?
C005 C006 1.467(3) . ?
C006 C008 1.381(3) . ?
C006 C009 1.389(3) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 S001 C005 86.96(9) . . ?
C005 N002 N003 113.93(16) . . ?
C007 N003 N002 111.90(16) . . ?
C00C C00A C00B 120.2(2) . . ?
H00A C00A C00B 119.92(17) . . ?
H00A C00A C00C 119.92(17) . . ?
C009 C00B C00A 120.2(3) . . ?
H00B C00B C00A 119.88(17) . . ?
H00B C00B C009 119.88(17) . . ?
C008 C00C C00A 119.7(3) . . ?
H00C C00C C00A 120.15(17) . . ?
H00C C00C C008 120.15(18) . . ?
H00d N004 C007 109.9 . . ?
H00e N004 C007 107.7 . . ?
H00e N004 H00d 109.5 . . ?
N002 C005 S001 113.19(15) . . ?
C006 C005 S001 122.63(15) . . ?
C006 C005 N002 124.15(18) . . ?
C008 C006 C005 121.2(2) . . ?
C009 C006 C005 120.0(2) . . ?
C009 C006 C008 118.7(2) . . ?
N003 C007 S001 114.02(15) . . ?
N004 C007 S001 122.13(15) . . ?
N004 C007 N003 123.83(19) . . ?
C006 C008 C00C 120.7(3) . . ?
H008 C008 C00C 119.67(18) . . ?
H008 C008 C006 119.67(14) . . ?
C006 C009 C00B 120.5(3) . . ?
H009 C009 C00B 119.75(17) . . ?
H009 C009 C006 119.75(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
