# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1481907'
_audit_update_record             
;
2016-05-25 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H2 N4, C12 H6 S'
_chemical_formula_sum            'C22 H10 N4 S'
_chemical_formula_weight         362.40
_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'
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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.435(6)
_cell_length_b                   12.771(8)
_cell_length_c                   7.237(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.021(9)
_cell_angle_gamma                90
_cell_volume                     870.8(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1381
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.363
_cell_measurement_theta_min      2.687
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
R(int) was 0.0789 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.8358.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tube
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2152
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.687
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                734
_reflns_number_total             842
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         842
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.102
_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)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1756
_refine_special_details          
;
 ?
;
_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
C1 C 0.87670(18) 0.55505(15) 0.9477(2) 0.0353(5) Uani 1 1 d . . . . .
C2 C 1.0000 0.6099(2) 1.0000 0.0385(7) Uani 1 2 d S T P . .
H2 H 1.0000 0.6828 1.0000 0.046 Uiso 1 2 calc R U P . .
C3 C 0.7489(2) 0.61191(16) 0.8934(3) 0.0431(6) Uani 1 1 d . . . . .
C4 C 0.2830(3) 0.4070(3) 0.6337(4) 0.0750(9) Uani 1 1 d . . . . .
H4 H 0.3306 0.3441 0.6562 0.090 Uiso 1 1 calc R U . . .
C5 C 0.3523(4) 0.5000 0.6666(5) 0.0651(12) Uani 1 2 d S T P . .
H5 H 0.4466 0.5000 0.7112 0.078 Uiso 1 2 calc R U P . .
C6 C 0.1449(4) 0.4058(4) 0.5685(5) 0.1091(17) Uani 1 1 d . U . . .
C7 C 0.0783(5) 0.4643(4) 0.5373(6) 0.0441(12) Uani 0.5 1 d . . P . .
N1 N 0.6488(2) 0.65797(18) 0.8504(3) 0.0621(7) Uani 1 1 d . . . . .
S1 S 0.0000 0.33496(13) 0.5000 0.0563(6) Uani 0.5 2 d S T P . .


_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 C1 1.406(4) 6_565 ?
C1 C2 1.393(2) . ?
C1 C3 1.445(3) . ?
C2 C1 1.393(2) 2_757 ?
C2 H2 0.9300 . ?
C3 N1 1.142(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C4 C6 1.362(5) . ?
C5 C4 1.371(4) 6_565 ?
C5 H5 0.9300 . ?
C6 C7 1.784(7) 6_565 ?
C6 C7 0.994(6) . ?
C6 S1 1.691(4) . ?
C7 C6 1.784(7) 6_565 ?
C7 C7 1.795(10) 5_566 ?
C7 C7 1.546(9) 2_556 ?
C7 C7 0.912(10) 6_565 ?
C7 S1 1.824(5) . ?
S1 C6 1.691(4) 2_556 ?
S1 C7 1.824(5) 2_556 ?

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
C1 C1 C3 120.18(11) 6_565 . ?
C2 C1 C1 120.21(13) . 6_565 ?
C2 C1 C3 119.61(18) . . ?
C1 C2 C1 119.6(3) . 2_757 ?
C1 C2 H2 120.2 2_757 . ?
C1 C2 H2 120.2 . . ?
N1 C3 C1 179.2(2) . . ?
C5 C4 H4 119.7 . . ?
C6 C4 H4 119.7 . . ?
C6 C4 C5 120.6(4) . . ?
C4 C5 C4 120.2(4) . 6_565 ?
C4 C5 H5 119.9 6_565 . ?
C4 C5 H5 119.9 . . ?
C4 C6 C7 110.9(4) . 6_565 ?
C4 C6 S1 148.3(5) . . ?
C7 C6 C4 130.6(6) . . ?
C7 C6 C7 19.7(3) . 6_565 ?
C7 C6 S1 81.1(4) . . ?
S1 C6 C7 100.8(2) . 6_565 ?
C6 C7 C6 117.2(5) . 6_565 ?
C6 C7 C7 161.8(7) . 5_566 ?
C6 C7 C7 81.0(3) 6_565 5_566 ?
C6 C7 C7 131.3(4) . 2_556 ?
C6 C7 S1 176.5(3) 6_565 . ?
C6 C7 S1 66.4(4) . . ?
C7 C7 C6 138.7(4) 6_565 . ?
C7 C7 C6 21.57(18) 6_565 6_565 ?
C7 C7 C6 111.57(18) 2_556 6_565 ?
C7 C7 C7 89.998(1) 6_565 2_556 ?
C7 C7 C7 59.5(3) 6_565 5_566 ?
C7 C7 C7 30.5(3) 2_556 5_566 ?
C7 C7 S1 95.4(3) 5_566 . ?
C7 C7 S1 64.91(15) 2_556 . ?
C7 C7 S1 154.91(15) 6_565 . ?
C6 S1 C6 115.3(4) . 2_556 ?
C6 S1 C7 82.8(3) 2_556 . ?
C6 S1 C7 32.6(2) . . ?
C6 S1 C7 82.8(3) . 2_556 ?
C6 S1 C7 32.6(2) 2_556 2_556 ?
C7 S1 C7 50.2(3) 2_556 . ?

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
C1 C1 C2 C1 0.003(0) 6_565 . . 2_757 ?
C3 C1 C2 C1 -179.96(18) . . . 2_757 ?
C4 C6 C7 C6 0.2(9) . . . 6_565 ?
C4 C6 C7 C7 0.2(9) . . . 6_565 ?
C4 C6 C7 C7 179.8(4) . . . 2_556 ?
C4 C6 C7 C7 179.5(16) . . . 5_566 ?
C4 C6 C7 S1 -180.0(5) . . . . ?
C4 C6 S1 C6 -180.0(5) . . . 2_556 ?
C4 C6 S1 C7 -179.9(5) . . . 2_556 ?
C4 C6 S1 C7 179.9(8) . . . . ?
C5 C4 C6 C7 -0.1(7) . . . . ?
C5 C4 C6 C7 0.0(4) . . . 6_565 ?
C5 C4 C6 S1 -180.0(4) . . . . ?
C6 C4 C5 C4 0.0(5) . . . 6_565 ?
C6 C7 S1 C6 -179.9(3) . . . 2_556 ?
C6 C7 S1 C7 -179.8(6) . . . 2_556 ?
C7 C6 C7 C6 0.002(2) 6_565 . . 6_565 ?
C7 C6 C7 C7 179(2) 6_565 . . 5_566 ?
C7 C6 C7 C7 179.7(11) 6_565 . . 2_556 ?
C7 C6 C7 S1 179.9(4) 6_565 . . . ?
C7 C6 S1 C6 0.05(17) 6_565 . . 2_556 ?
C7 C6 S1 C6 0.1(3) . . . 2_556 ?
C7 C6 S1 C7 0.1(3) 6_565 . . 2_556 ?
C7 C6 S1 C7 -0.04(14) 6_565 . . . ?
C7 C6 S1 C7 0.1(5) . . . 2_556 ?
C7 C7 S1 C6 -0.1(3) 6_565 . . 2_556 ?
C7 C7 S1 C6 179.8(6) 5_566 . . . ?
C7 C7 S1 C6 -0.1(3) 2_556 . . 2_556 ?
C7 C7 S1 C6 -0.1(3) 5_566 . . 2_556 ?
C7 C7 S1 C6 179.8(6) 6_565 . . . ?
C7 C7 S1 C6 179.8(6) 2_556 . . . ?
C7 C7 S1 C7 0.002(2) 6_565 . . 2_556 ?
C7 C7 S1 C7 0.000(1) 5_566 . . 2_556 ?
S1 C6 C7 C6 -179.9(4) . . . 6_565 ?
S1 C6 C7 C7 -0.2(7) . . . 2_556 ?
S1 C6 C7 C7 -179.9(4) . . . 6_565 ?
S1 C6 C7 C7 -1(2) . . . 5_566 ?

_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.944
_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.
;
_shelxl_version_number           2014-3
