# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_5ba
_database_code_depnum_ccdc_archive 'CCDC 1967009'
loop_
_audit_author_name
_audit_author_address
'Adrian Perez-Redondo'
;Universidad de Alcala
Spain
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;

_audit_creation_date             2019-07-19T15:52:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H9 N3 O2 S'
_chemical_formula_sum            'C11 H9 N3 O2 S'
_chemical_formula_weight         247.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9735(3)
_cell_length_b                   7.8762(2)
_cell_length_c                   9.8077(4)
_cell_angle_alpha                99.965(3)
_cell_angle_beta                 95.925(4)
_cell_angle_gamma                97.050(3)
_cell_volume                     522.26(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    70
_cell_measurement_theta_min      3
_cell_measurement_theta_max      21
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.225
1 -2 0 0.336
-1 -7 0 0.416
-4 3 0 0.271
1 11 0 0.32
-1 -18 13 0.292
1 -2 -14 0.208
-1 2 14 0.203


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.002796
_diffrn_orient_matrix_ub_12      0.06034
_diffrn_orient_matrix_ub_13      0.09811
_diffrn_orient_matrix_ub_21      0.13111
_diffrn_orient_matrix_ub_22      -0.031656
_diffrn_orient_matrix_ub_23      0.027692
_diffrn_orient_matrix_ub_31      0.063438
_diffrn_orient_matrix_ub_32      0.111013
_diffrn_orient_matrix_ub_33      -0.022389
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_number            13956
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2389
_reflns_number_gt                2086
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.2354P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.042
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.132

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
C1 C 0.6334(2) 0.3160(2) 0.36945(17) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.6144(3) 0.2364(2) 0.58047(19) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.573 0.1515 0.6333 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7134(3) 0.3946(3) 0.65157(18) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.7376 0.4182 0.7506 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7767(2) 0.5181(2) 0.57506(17) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.8455 0.628 0.6214 0.03 Uiso 1 1 calc R U . . .
C5 C 0.7389(2) 0.4805(2) 0.42996(17) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.7985(2) 0.6074(2) 0.34381(17) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.9112(3) 0.8882(2) 0.3273(2) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.9565 1.0054 0.3718 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9019(3) 0.8475(2) 0.1829(2) 0.0327(4) Uani 1 1 d . . . . .
H8 H 0.9377 0.935 0.131 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8396(3) 0.6776(2) 0.11662(19) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.8314 0.6444 0.0181 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7892(2) 0.5570(2) 0.19911(17) 0.0215(3) Uani 1 1 d . . . . .
C11 C 0.4338(3) 0.1161(2) 0.1661(2) 0.0356(4) Uani 1 1 d . . . . .
H11A H 0.4964 0.0125 0.1726 0.053 Uiso 1 1 calc R U . . .
H11B H 0.3888 0.1161 0.0681 0.053 Uiso 1 1 calc R U . . .
H11C H 0.3224 0.115 0.2193 0.053 Uiso 1 1 calc R U . . .
N1 N 0.5750(2) 0.27365(18) 0.22358(15) 0.0249(3) Uani 1 1 d . . . . .
N2 N 0.5733(2) 0.19579(19) 0.44114(16) 0.0274(3) Uani 1 1 d . . . . .
N3 N 0.8609(2) 0.77380(18) 0.40751(15) 0.0260(3) Uani 1 1 d . . . . .
O1 O 0.6384(2) 0.31297(18) -0.01557(13) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.9088(2) 0.25802(16) 0.14374(14) 0.0324(3) Uani 1 1 d . . . . .
S1 S 0.73467(6) 0.33645(5) 0.12379(4) 0.02431(15) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N2 1.327(2) . ?
C1 C5 1.407(2) . ?
C1 N1 1.416(2) . ?
C2 N2 1.341(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.95 . ?
C3 C4 1.386(2) . ?
C3 H3 0.95 . ?
C4 C5 1.393(2) . ?
C4 H4 0.95 . ?
C5 C6 1.466(2) . ?
C6 N3 1.348(2) . ?
C6 C10 1.398(2) . ?
C7 N3 1.334(2) . ?
C7 C8 1.389(3) . ?
C7 H7 0.95 . ?
C8 C9 1.379(3) . ?
C8 H8 0.95 . ?
C9 C10 1.387(2) . ?
C9 H9 0.95 . ?
C10 S1 1.7445(16) . ?
C11 N1 1.473(2) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
N1 S1 1.6433(15) . ?
O1 S1 1.4303(14) . ?
O2 S1 1.4391(14) . ?

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
N2 C1 C5 124.34(15) . . ?
N2 C1 N1 115.53(14) . . ?
C5 C1 N1 120.04(14) . . ?
N2 C2 C3 123.75(16) . . ?
N2 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 118.41(16) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.69(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C1 116.69(15) . . ?
C4 C5 C6 122.08(15) . . ?
C1 C5 C6 121.18(15) . . ?
N3 C6 C10 120.99(15) . . ?
N3 C6 C5 118.33(15) . . ?
C10 C6 C5 120.68(14) . . ?
N3 C7 C8 124.38(16) . . ?
N3 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
C9 C8 C7 118.65(16) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 117.51(16) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C6 120.92(15) . . ?
C9 C10 S1 119.57(13) . . ?
C6 C10 S1 119.26(12) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C11 118.98(14) . . ?
C1 N1 S1 116.57(11) . . ?
C11 N1 S1 117.70(12) . . ?
C1 N2 C2 117.10(15) . . ?
C7 N3 C6 117.53(15) . . ?
O1 S1 O2 117.39(9) . . ?
O1 S1 N1 108.33(8) . . ?
O2 S1 N1 110.93(8) . . ?
O1 S1 C10 111.02(8) . . ?
O2 S1 C10 108.02(8) . . ?
N1 S1 C10 99.71(7) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
