# 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 2019

####################################################################### 
# 
# 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_Compound_1a
_database_code_depnum_ccdc_archive 'CCDC 1863612'
loop_
_audit_author_name
_audit_author_address
'Rub?n A. Toscano'
;Instituto de Qu?mica, UNAM
Mexico
;
_audit_update_record             
;
2018-08-23 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N3 S'
_chemical_formula_sum            'C17 H15 N3 S'
_chemical_formula_weight         293.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.1601(7)
_cell_length_b                   11.5158(6)
_cell_length_c                   12.7909(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.834(2)
_cell_angle_gamma                90
_cell_volume                     1536.37(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5270
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      22.26

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.269
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7956
_exptl_absorpt_correction_T_max  0.8746
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            31989
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.635
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3382
_reflns_number_gt                1980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.2483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.91531(5) 0.38291(5) 0.25971(5) 0.0694(2) Uani 1 1 d . . . . .
N1 N 0.72579(13) 0.27887(13) 0.11593(12) 0.0491(4) Uani 1 1 d . . . . .
N2 N 0.70065(13) 0.51362(13) 0.28651(12) 0.0477(4) Uani 1 1 d . . . . .
N3 N 0.61756(14) 0.57907(13) 0.31696(13) 0.0531(4) Uani 1 1 d . . . . .
C1 C 0.8234(2) 0.12561(19) 0.03598(18) 0.0737(6) Uani 1 1 d . . . . .
H1A H 0.783656 0.151702 -0.039841 0.111 Uiso 1 1 calc R U . . .
H1B H 0.771763 0.065881 0.051111 0.111 Uiso 1 1 calc R U . . .
H1C H 0.907007 0.095252 0.046611 0.111 Uiso 1 1 calc R U . . .
C2 C 0.83534(18) 0.22515(17) 0.11386(15) 0.0510(5) Uani 1 1 d . . . . .
C3 C 0.94457(19) 0.27064(19) 0.18504(16) 0.0643(6) Uani 1 1 d . . . . .
H3 H 1.026039 0.244275 0.192736 0.077 Uiso 1 1 calc R U . . .
C4 C 0.75406(16) 0.36296(16) 0.18916(14) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.65964(17) 0.43278(16) 0.21375(15) 0.0486(5) Uani 1 1 d . . . . .
H5 H 0.572342 0.419454 0.178016 0.058 Uiso 1 1 calc R U . . .
C6 C 0.67159(16) 0.66538(15) 0.39821(14) 0.0457(4) Uani 1 1 d . . . . .
C7 C 0.59374(18) 0.72971(17) 0.44048(15) 0.0543(5) Uani 1 1 d . . . . .
H7 H 0.506123 0.715089 0.416238 0.065 Uiso 1 1 calc R U . . .
C8 C 0.6470(2) 0.81519(18) 0.51842(17) 0.0650(6) Uani 1 1 d . . . . .
H8 H 0.594313 0.858600 0.545851 0.078 Uiso 1 1 calc R U . . .
C9 C 0.7759(2) 0.83762(19) 0.55640(18) 0.0707(6) Uani 1 1 d . . . . .
H9 H 0.810731 0.895698 0.608986 0.085 Uiso 1 1 calc R U . . .
C10 C 0.85302(19) 0.77273(19) 0.51541(17) 0.0657(6) Uani 1 1 d . . . . .
H10 H 0.940741 0.787073 0.540904 0.079 Uiso 1 1 calc R U . . .
C11 C 0.80228(17) 0.68712(16) 0.43741(16) 0.0547(5) Uani 1 1 d . . . . .
H11 H 0.855680 0.643680 0.410854 0.066 Uiso 1 1 calc R U . . .
C12 C 0.48209(16) 0.55440(16) 0.27568(15) 0.0470(5) Uani 1 1 d . . . . .
C13 C 0.40114(19) 0.61415(18) 0.18587(17) 0.0606(5) Uani 1 1 d . . . . .
H13 H 0.432780 0.671994 0.152003 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2714(2) 0.5877(2) 0.14580(18) 0.0724(6) Uani 1 1 d . . . . .
H14 H 0.215996 0.627721 0.084541 0.087 Uiso 1 1 calc R U . . .
C15 C 0.2249(2) 0.5036(2) 0.19540(19) 0.0726(7) Uani 1 1 d . . . . .
H15 H 0.137626 0.486857 0.168433 0.087 Uiso 1 1 calc R U . . .
C16 C 0.3058(2) 0.4435(2) 0.28487(19) 0.0723(6) Uani 1 1 d . . . . .
H16 H 0.273816 0.385314 0.318085 0.087 Uiso 1 1 calc R U . . .
C17 C 0.43529(19) 0.46914(18) 0.32597(17) 0.0611(5) Uani 1 1 d . . . . .
H17 H 0.490424 0.428938 0.387297 0.073 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 C3 1.707(2) . ?
S1 C4 1.7176(18) . ?
N1 C4 1.306(2) . ?
N1 C2 1.379(2) . ?
N2 C5 1.280(2) . ?
N2 N3 1.3552(19) . ?
N3 C6 1.409(2) . ?
N3 C12 1.441(2) . ?
C1 C2 1.493(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.342(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.446(2) . ?
C5 H5 0.9300 . ?
C6 C11 1.386(2) . ?
C6 C7 1.389(2) . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.368(3) . ?
C12 C17 1.375(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
C3 S1 C4 88.73(9) . . ?
C4 N1 C2 110.91(15) . . ?
C5 N2 N3 120.60(15) . . ?
N2 N3 C6 116.56(14) . . ?
N2 N3 C12 121.39(14) . . ?
C6 N3 C12 121.82(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 114.19(17) . . ?
C3 C2 C1 126.63(18) . . ?
N1 C2 C1 119.19(17) . . ?
C2 C3 S1 111.54(14) . . ?
C2 C3 H3 124.2 . . ?
S1 C3 H3 124.2 . . ?
N1 C4 C5 124.03(17) . . ?
N1 C4 S1 114.63(13) . . ?
C5 C4 S1 121.31(14) . . ?
N2 C5 C4 117.56(17) . . ?
N2 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C11 C6 C7 119.09(17) . . ?
C11 C6 N3 120.90(16) . . ?
C7 C6 N3 120.02(16) . . ?
C8 C7 C6 119.65(18) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 121.34(19) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 120.94(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 120.10(18) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 120.32(17) . . ?
C13 C12 N3 120.13(17) . . ?
C17 C12 N3 119.53(17) . . ?
C12 C13 C14 119.38(19) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.63(19) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?

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
C5 N2 N3 C6 179.54(15) . . . . ?
C5 N2 N3 C12 5.0(2) . . . . ?
C4 N1 C2 C3 -0.6(2) . . . . ?
C4 N1 C2 C1 179.45(16) . . . . ?
N1 C2 C3 S1 0.6(2) . . . . ?
C1 C2 C3 S1 -179.47(16) . . . . ?
C4 S1 C3 C2 -0.33(17) . . . . ?
C2 N1 C4 C5 -177.61(16) . . . . ?
C2 N1 C4 S1 0.35(19) . . . . ?
C3 S1 C4 N1 -0.02(15) . . . . ?
C3 S1 C4 C5 178.00(16) . . . . ?
N3 N2 C5 C4 -177.20(15) . . . . ?
N1 C4 C5 N2 -179.07(15) . . . . ?
S1 C4 C5 N2 3.1(2) . . . . ?
N2 N3 C6 C11 5.0(2) . . . . ?
C12 N3 C6 C11 179.51(16) . . . . ?
N2 N3 C6 C7 -174.77(15) . . . . ?
C12 N3 C6 C7 -0.2(3) . . . . ?
C11 C6 C7 C8 1.4(3) . . . . ?
N3 C6 C7 C8 -178.90(17) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C7 C6 C11 C10 -1.2(3) . . . . ?
N3 C6 C11 C10 179.05(17) . . . . ?
N2 N3 C12 C13 -97.2(2) . . . . ?
C6 N3 C12 C13 88.6(2) . . . . ?
N2 N3 C12 C17 81.7(2) . . . . ?
C6 N3 C12 C17 -92.6(2) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
N3 C12 C13 C14 178.68(18) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
N3 C12 C17 C16 -178.50(18) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 N1 0.93 2.58 3.425(2) 151.4 2_655 yes

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042

