# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_test555_a
_database_code_depnum_ccdc_archive 'CCDC 2107203'
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N4 S'
_chemical_formula_sum            'C21 H14 N4 S'
_chemical_formula_weight         354.42
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.201(7)
_cell_length_b                   3.9233(10)
_cell_length_c                   37.778(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.480(8)
_cell_angle_gamma                90
_cell_volume                     3845.3(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    129(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5506
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1086 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.7389.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            13614
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      128.5
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2179
_reflns_number_total             3386
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0792
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+7.7249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_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
S001 S 0.38780(4) 0.8096(3) 0.78845(3) 0.0376(3) Uani 1 1 d . . . . .
N002 N 0.48033(14) 1.0184(9) 0.79213(9) 0.0376(9) Uani 1 1 d . . . . .
N003 N 0.38762(14) 0.6784(9) 0.71349(9) 0.0380(9) Uani 1 1 d . . . . .
N004 N 0.43259(14) 0.8196(10) 0.73386(9) 0.0430(10) Uani 1 1 d . . . . .
H004 H 0.457281 0.863709 0.723897 0.052 Uiso 1 1 calc R . . . .
C005 C 0.47455(17) 1.0643(10) 0.82740(11) 0.0330(10) Uani 1 1 d . . . . .
N006 N 0.24530(15) 0.2617(10) 0.59680(10) 0.0477(10) Uani 1 1 d . . . . .
C007 C 0.33009(17) 0.5330(10) 0.61388(11) 0.0343(10) Uani 1 1 d . . . . .
C008 C 0.29572(16) 0.3229(10) 0.66258(11) 0.0339(10) Uani 1 1 d . . . . .
C009 C 0.43863(16) 0.8916(10) 0.77013(11) 0.0335(10) Uani 1 1 d . . . . .
C00A C 0.42702(17) 0.9654(10) 0.83078(11) 0.0342(10) Uani 1 1 d . . . . .
C00B C 0.33554(17) 0.4938(10) 0.65239(11) 0.0351(10) Uani 1 1 d . . . . .
C00C C 0.51155(19) 1.2001(11) 0.85791(12) 0.0444(11) Uani 1 1 d . . . . .
H00C H 0.544136 1.268264 0.855940 0.053 Uiso 1 1 calc R . . . .
C00D C 0.38196(17) 0.6329(11) 0.67884(11) 0.0380(11) Uani 1 1 d . . . . .
H00D H 0.409804 0.693844 0.669804 0.046 Uiso 1 1 calc R . . . .
C00E C 0.36754(19) 0.6921(11) 0.59916(12) 0.0448(12) Uani 1 1 d . . . . .
H00E H 0.398510 0.778777 0.615800 0.054 Uiso 1 1 calc R . . . .
C00F C 0.28411(19) 0.4125(11) 0.58740(12) 0.0428(12) Uani 1 1 d . . . . .
C00G C 0.25181(18) 0.2133(11) 0.63364(12) 0.0407(11) Uani 1 1 d . . . . .
C00H C 0.21082(19) 0.0395(12) 0.64233(15) 0.0510(13) Uani 1 1 d . . . . .
H00H H 0.181425 -0.031580 0.622912 0.061 Uiso 1 1 calc R . . . .
C00I C 0.29740(19) 0.2484(11) 0.69981(12) 0.0441(12) Uani 1 1 d . . . . .
H00I H 0.326318 0.314908 0.719857 0.053 Uiso 1 1 calc R . . . .
C00J C 0.5007(2) 1.2353(12) 0.89108(12) 0.0525(13) Uani 1 1 d . . . . .
H00J H 0.525648 1.331278 0.911929 0.063 Uiso 1 1 calc R . . . .
C00K C 0.4157(2) 1.0004(12) 0.86413(12) 0.0502(13) Uani 1 1 d . . . . .
H00K H 0.382999 0.935808 0.866075 0.060 Uiso 1 1 calc R . . . .
C00L C 0.2570(2) 0.0802(11) 0.70649(14) 0.0507(13) Uani 1 1 d . . . . .
H00L H 0.258617 0.033050 0.731483 0.061 Uiso 1 1 calc R . . . .
C00M C 0.4530(2) 1.1305(13) 0.89418(13) 0.0538(14) Uani 1 1 d . . . . .
H00M H 0.446271 1.149532 0.917376 0.065 Uiso 1 1 calc R . . . .
C00N C 0.2771(2) 0.4544(13) 0.54853(13) 0.0577(14) Uani 1 1 d . . . . .
H00N H 0.246096 0.380228 0.530937 0.069 Uiso 1 1 calc R . . . .
C00O C 0.2136(2) -0.0252(12) 0.67831(15) 0.0526(13) Uani 1 1 d . . . . .
H00O H 0.186283 -0.140597 0.684118 0.063 Uiso 1 1 calc R . . . .
C00P C 0.3596(2) 0.7205(12) 0.56230(13) 0.0545(13) Uani 1 1 d . . . . .
H00P H 0.385150 0.825381 0.553470 0.065 Uiso 1 1 calc R . . . .
C00Q C 0.3144(2) 0.5984(14) 0.53683(14) 0.0617(15) Uani 1 1 d . . . . .
H00Q H 0.309996 0.617319 0.510991 0.074 Uiso 1 1 calc R . . . .


_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
S001 C009 1.752(4) . ?
S001 C00A 1.745(4) . ?
N002 C005 1.399(5) . ?
N002 C009 1.288(5) . ?
N003 N004 1.353(5) . ?
N003 C00D 1.284(5) . ?
N004 H004 0.8800 . ?
N004 C009 1.360(5) . ?
C005 C00A 1.392(6) . ?
C005 C00C 1.389(6) . ?
N006 C00F 1.347(6) . ?
N006 C00G 1.362(5) . ?
C007 C00B 1.426(5) . ?
C007 C00E 1.441(6) . ?
C007 C00F 1.427(6) . ?
C008 C00B 1.422(6) . ?
C008 C00G 1.422(6) . ?
C008 C00I 1.424(6) . ?
C00A C00K 1.390(5) . ?
C00B C00D 1.461(6) . ?
C00C H00C 0.9500 . ?
C00C C00J 1.378(6) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00P 1.348(6) . ?
C00F C00N 1.433(6) . ?
C00G C00H 1.427(6) . ?
C00H H00H 0.9500 . ?
C00H C00O 1.362(6) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.369(6) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.399(7) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.373(7) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.394(7) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00Q 1.346(7) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.398(7) . ?
C00Q H00Q 0.9500 . ?

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
C00A S001 C009 87.7(2) . . ?
C009 N002 C005 109.6(3) . . ?
C00D N003 N004 116.6(3) . . ?
N003 N004 H004 120.9 . . ?
N003 N004 C009 118.2(3) . . ?
C009 N004 H004 120.9 . . ?
C00A C005 N002 115.1(4) . . ?
C00C C005 N002 125.4(4) . . ?
C00C C005 C00A 119.5(4) . . ?
C00F N006 C00G 117.3(4) . . ?
C00B C007 C00E 124.9(4) . . ?
C00B C007 C00F 118.7(4) . . ?
C00F C007 C00E 116.4(4) . . ?
C00B C008 C00G 117.8(4) . . ?
C00B C008 C00I 124.3(4) . . ?
C00G C008 C00I 117.9(4) . . ?
N002 C009 S001 117.6(3) . . ?
N002 C009 N004 123.2(4) . . ?
N004 C009 S001 119.3(3) . . ?
C005 C00A S001 110.0(3) . . ?
C00K C00A S001 128.7(4) . . ?
C00K C00A C005 121.3(4) . . ?
C007 C00B C00D 117.5(4) . . ?
C008 C00B C007 118.2(4) . . ?
C008 C00B C00D 124.3(4) . . ?
C005 C00C H00C 120.2 . . ?
C00J C00C C005 119.5(4) . . ?
C00J C00C H00C 120.2 . . ?
N003 C00D C00B 124.3(4) . . ?
N003 C00D H00D 117.8 . . ?
C00B C00D H00D 117.8 . . ?
C007 C00E H00E 119.3 . . ?
C00P C00E C007 121.5(5) . . ?
C00P C00E H00E 119.3 . . ?
N006 C00F C007 123.5(4) . . ?
N006 C00F C00N 116.6(5) . . ?
C007 C00F C00N 119.9(4) . . ?
N006 C00G C008 124.4(4) . . ?
N006 C00G C00H 115.5(4) . . ?
C008 C00G C00H 120.1(4) . . ?
C00G C00H H00H 119.8 . . ?
C00O C00H C00G 120.4(5) . . ?
C00O C00H H00H 119.8 . . ?
C008 C00I H00I 120.3 . . ?
C00L C00I C008 119.5(5) . . ?
C00L C00I H00I 120.3 . . ?
C00C C00J H00J 119.8 . . ?
C00C C00J C00M 120.3(4) . . ?
C00M C00J H00J 119.8 . . ?
C00A C00K H00K 120.7 . . ?
C00M C00K C00A 118.5(5) . . ?
C00M C00K H00K 120.7 . . ?
C00I C00L H00L 118.5 . . ?
C00I C00L C00O 123.0(5) . . ?
C00O C00L H00L 118.5 . . ?
C00J C00M H00M 119.6 . . ?
C00K C00M C00J 120.8(4) . . ?
C00K C00M H00M 119.6 . . ?
C00F C00N H00N 119.9 . . ?
C00Q C00N C00F 120.3(5) . . ?
C00Q C00N H00N 119.9 . . ?
C00H C00O C00L 119.1(5) . . ?
C00H C00O H00O 120.4 . . ?
C00L C00O H00O 120.4 . . ?
C00E C00P H00P 119.4 . . ?
C00E C00P C00Q 121.1(5) . . ?
C00Q C00P H00P 119.4 . . ?
C00N C00Q C00P 120.7(5) . . ?
C00N C00Q H00Q 119.6 . . ?
C00P C00Q H00Q 119.6 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.672 0.000 193.6 56.3 ?
2 0.000 -0.964 0.500 193.6 56.3 ?
3 0.500 -0.255 0.000 193.6 56.3 ?
4 0.500 -0.791 0.500 193.6 56.3 ?

_olex2_submission_special_instructions 'No special instructions were received'
