# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1824689'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N5 S'
_chemical_formula_sum            'C18 H15 N5 S'
_chemical_formula_weight         333.41

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_H-M_alt        'I 41'
_space_group_name_Hall           'I 4bw'

_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'
'-y, x+1/2, z+1/4'
'-x, -y, z'
'y, -x+1/2, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1, z+3/4'

_cell_length_a                   12.8855(4)
_cell_length_b                   12.8855(4)
_cell_length_c                   19.6018(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3254.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1989
_cell_measurement_theta_min      4.106
_cell_measurement_theta_max      71.691

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    1.834
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3244
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.106
_diffrn_reflns_theta_max         71.691
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_point_group_measured_fraction_full 0.681
_reflns_number_total             2111
_reflns_number_gt                1989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.320
_reflns_Friedel_fraction_max     0.331
_reflns_Friedel_fraction_full    0.349

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0564P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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 0.84373(7) 0.46301(7) -0.05742(4) 0.0590(2) Uani 1 1 d . . . . .
N1 N 0.86363(19) 0.39616(18) 0.41007(13) 0.0418(5) Uani 1 1 d . . . . .
N2 N 0.87967(18) 0.74966(18) 0.37449(13) 0.0405(5) Uani 1 1 d . . . . .
N3 N 0.87160(17) 0.57224(18) 0.38870(13) 0.0397(5) Uani 1 1 d . . . . .
C4 C 0.8612(3) 0.4046(3) 0.47880(17) 0.0517(8) Uani 1 1 d . . . . .
H4 H 0.8617 0.4657 0.5040 0.062 Uiso 1 1 calc R U . . .
C5 C 0.8813(2) 0.7725(2) 0.44200(17) 0.0475(6) Uani 1 1 d . . . . .
H5 H 0.8781 0.7256 0.4780 0.057 Uiso 1 1 calc R U . . .
N6 N 0.8853(2) 0.83582(19) 0.33498(14) 0.0476(6) Uani 1 1 d . . . . .
C7 C 0.8747(2) 0.6502(2) 0.34425(15) 0.0387(6) Uani 1 1 d . . . . .
C8 C 0.8655(2) 0.5389(2) 0.24685(16) 0.0396(6) Uani 1 1 d . . . . .
C9 C 0.8716(2) 0.6393(2) 0.27447(16) 0.0416(6) Uani 1 1 d . . . . .
H9 H 0.8736 0.6972 0.2462 0.050 Uiso 1 1 calc R U . . .
C10 C 0.8638(2) 0.4564(2) 0.29249(16) 0.0416(6) Uani 1 1 d . . . . .
H10 H 0.8607 0.3883 0.2769 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8885(3) 0.8781(2) 0.44662(19) 0.0543(7) Uani 1 1 d . . . . .
H11 H 0.8913 0.9181 0.4860 0.065 Uiso 1 1 calc R U . . .
N12 N 0.8613(2) 0.2962(2) 0.38893(15) 0.0501(6) Uani 1 1 d . . . . .
C13 C 0.8667(2) 0.4777(2) 0.36172(16) 0.0391(6) Uani 1 1 d . . . . .
C14 C 0.8603(2) 0.5220(2) 0.17221(15) 0.0405(6) Uani 1 1 d . . . . .
C15 C 0.8237(3) 0.4291(2) 0.14499(17) 0.0506(7) Uani 1 1 d . . . . .
H15 H 0.8016 0.3765 0.1741 0.061 Uiso 1 1 calc R U . . .
C16 C 0.8509(2) 0.4915(2) 0.03000(16) 0.0451(6) Uani 1 1 d . . . . .
C17 C 0.8198(3) 0.4140(3) 0.07510(18) 0.0522(7) Uani 1 1 d . . . . .
H17 H 0.7960 0.3511 0.0580 0.063 Uiso 1 1 calc R U . . .
C18 C 0.8876(3) 0.5829(2) 0.05671(18) 0.0552(8) Uani 1 1 d . . . . .
H18 H 0.9094 0.6356 0.0276 0.066 Uiso 1 1 calc R U . . .
C19 C 0.8584(3) 0.2426(2) 0.4463(2) 0.0537(7) Uani 1 1 d . . . . .
H19 H 0.8570 0.1705 0.4481 0.064 Uiso 1 1 calc R U . . .
C20 C 0.8578(3) 0.3063(3) 0.50395(19) 0.0569(8) Uani 1 1 d . . . . .
H20 H 0.8556 0.2860 0.5495 0.068 Uiso 1 1 calc R U . . .
C21 C 0.8922(3) 0.5973(2) 0.12631(18) 0.0550(8) Uani 1 1 d . . . . .
H21 H 0.9176 0.6598 0.1431 0.066 Uiso 1 1 calc R U . . .
C22 C 0.8907(3) 0.9124(2) 0.37917(18) 0.0510(7) Uani 1 1 d . . . . .
H22 H 0.8954 0.9819 0.3668 0.061 Uiso 1 1 calc R U . . .
C23 C 0.8739(3) 0.5833(4) -0.0987(2) 0.0725(11) Uani 1 1 d . . . . .
H23A H 0.8279 0.6364 -0.0824 0.109 Uiso 1 1 calc R U . . .
H23B H 0.8656 0.5757 -0.1471 0.109 Uiso 1 1 calc R U . . .
H23C H 0.9443 0.6023 -0.0887 0.109 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 C16 1.755(3) . ?
S1 C23 1.791(4) . ?
N1 C4 1.352(4) . ?
N1 N12 1.353(3) . ?
N1 C13 1.415(4) . ?
N2 N6 1.356(3) . ?
N2 C5 1.356(4) . ?
N2 C7 1.413(3) . ?
N3 C13 1.330(4) . ?
N3 C7 1.330(4) . ?
C4 C20 1.360(5) . ?
C5 C11 1.366(4) . ?
N6 C22 1.315(4) . ?
C7 C9 1.376(4) . ?
C8 C10 1.390(4) . ?
C8 C9 1.404(4) . ?
C8 C14 1.481(4) . ?
C10 C13 1.385(4) . ?
C11 C22 1.395(5) . ?
N12 C19 1.320(5) . ?
C14 C21 1.385(4) . ?
C14 C15 1.394(4) . ?
C15 C17 1.384(5) . ?
C16 C18 1.373(5) . ?
C16 C17 1.392(4) . ?
C18 C21 1.378(5) . ?
C19 C20 1.397(5) . ?

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
C16 S1 C23 104.41(19) . . ?
C4 N1 N12 112.4(3) . . ?
C4 N1 C13 127.5(3) . . ?
N12 N1 C13 120.1(3) . . ?
N6 N2 C5 112.3(2) . . ?
N6 N2 C7 120.4(2) . . ?
C5 N2 C7 127.4(3) . . ?
C13 N3 C7 115.7(3) . . ?
N1 C4 C20 106.7(3) . . ?
N2 C5 C11 106.4(3) . . ?
C22 N6 N2 104.0(3) . . ?
N3 C7 C9 125.0(3) . . ?
N3 C7 N2 114.3(3) . . ?
C9 C7 N2 120.7(3) . . ?
C10 C8 C9 117.2(3) . . ?
C10 C8 C14 121.5(3) . . ?
C9 C8 C14 121.2(3) . . ?
C7 C9 C8 118.6(3) . . ?
C13 C10 C8 118.6(3) . . ?
C5 C11 C22 104.7(3) . . ?
C19 N12 N1 103.8(3) . . ?
N3 C13 C10 124.9(3) . . ?
N3 C13 N1 114.5(3) . . ?
C10 C13 N1 120.6(3) . . ?
C21 C14 C15 116.9(3) . . ?
C21 C14 C8 121.7(3) . . ?
C15 C14 C8 121.3(3) . . ?
C17 C15 C14 120.8(3) . . ?
C18 C16 C17 118.2(3) . . ?
C18 C16 S1 124.7(3) . . ?
C17 C16 S1 117.1(2) . . ?
C15 C17 C16 121.2(3) . . ?
C16 C18 C21 120.5(3) . . ?
N12 C19 C20 112.5(3) . . ?
C4 C20 C19 104.7(3) . . ?
C18 C21 C14 122.5(3) . . ?
N6 C22 C11 112.7(3) . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.046

