# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_4_pl
_database_code_depnum_ccdc_archive 'CCDC 2368641'
loop_
_audit_author_name
_audit_author_address
'Wenjin Yan'
;Dalian University of Technology
China
;
_audit_update_record             
;
2024-07-08 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            Phpm
_chemical_name_systematic        TAC-HMTA
_chemical_formula_moiety         '2(C3 H3 N3 S3), 2(C6 H12 N4)'
_chemical_formula_sum            'C18 H30 N14 S6'
_chemical_formula_weight         634.92
_chemical_absolute_configuration ?
_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      hexagonal
_space_group_IT_number           186
_space_group_name_H-M_alt        'P 63 m c'
_space_group_name_Hall           'P 6c -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'y, x, z+1/2'
'-x+y, y, z'
'-x, -x+y, z+1/2'
'-y, -x, z'
'x-y, -y, z+1/2'
'x, x-y, z'

_cell_length_a                   9.6534(18)
_cell_length_b                   9.6534(18)
_cell_length_c                   16.438(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1326.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      24.768
_cell_measurement_theta_min      2.436
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0885 after correction.
The Ratio of minimum to maximum transmission is 0.7994.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8697
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.065
_diffrn_reflns_theta_max         25.065
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                773
_reflns_number_total             931
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         931
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.056
_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)+(0.0606P)²+1.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(4)
 -0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H5A(0.5) H5B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2)
;
_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
S1 S -0.51503(12) -1.0301(2) 0.35353(15) 0.0155(6) Uani 1 2 d S T P . .
N1 N -0.4922(10) -0.7461(5) 0.3427(5) 0.0142(18) Uani 1 2 d S T P . .
H1 H -0.597151 -0.798575 0.338467 0.017 Uiso 1 2 calc R U P . .
C1 C -0.4153(5) -0.8306(10) 0.3458(6) 0.013(2) Uiso 1 2 d S . P . .
S2 S -0.3028(2) -0.15138(12) 0.64022(15) 0.0153(6) Uani 1 2 d S T P . .
N2 N -0.5864(5) -0.4136(5) 0.6488(6) 0.0100(17) Uani 1 2 d S T P . .
H2 H -0.533834 -0.466168 0.650668 0.012 Uiso 1 2 calc R U P . .
C2 C -0.5000(10) -0.2500(5) 0.6474(6) 0.012(2) Uiso 1 2 d S . P . .
N3 N -0.8331(9) -0.9165(4) 0.3597(5) 0.0129(17) Uani 1 2 d S T P . .
N5 N -1.000000 -1.000000 0.4813(7) 0.011(3) Uani 1 6 d S T P . .
C3 C -0.9169(7) -0.8339(14) 0.3301(6) 0.015(2) Uani 1 2 d S T P . .
H3A H -0.860913 -0.721826 0.349543 0.018 Uiso 1 2 calc R U P . .
H3B H -0.916197 -0.832397 0.269837 0.018 Uiso 1 2 calc R U P . .
C4 C -0.8366(12) -0.9183(6) 0.4510(5) 0.014(2) Uani 1 2 d S T P . .
H4A H -0.780022 -0.972986 0.471631 0.017 Uiso 0.5 1 calc R U P . .
H4B H -0.780022 -0.807036 0.471631 0.017 Uiso 0.5 1 calc R U P . .
N4 N -0.4175(4) -0.5825(4) 0.6428(5) 0.0104(15) Uani 1 2 d S T P . .
N6 N -0.333333 -0.666667 0.5211(7) 0.015(3) Uani 1 6 d S T P . .
C5 C -0.4148(7) -0.5852(7) 0.5517(5) 0.014(2) Uani 1 2 d S T P . .
H5A H -0.525966 -0.639861 0.531026 0.017 Uiso 0.5 1 calc R U P . .
H5B H -0.360139 -0.474034 0.531026 0.017 Uiso 0.5 1 calc R U P . .
C6 C -0.2500(6) -0.4999(12) 0.6724(5) 0.011(2) Uani 1 2 d S T P . .
H6A H -0.249183 -0.498368 0.732584 0.014 Uiso 1 2 calc R U P . .
H6B H -0.193940 -0.387880 0.652905 0.014 Uiso 1 2 calc R U 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
S1 C1 1.672(9) . ?
N1 H1 0.8800 . ?
N1 C1 1.351(6) 5_545 ?
N1 C1 1.351(6) . ?
S2 C2 1.653(9) . ?
N2 H2 0.8800 . ?
N2 C2 1.369(6) . ?
N2 C2 1.369(6) 5_445 ?
N3 C3 1.475(7) 5_435 ?
N3 C3 1.475(7) . ?
N3 C4 1.502(13) . ?
N5 C4 1.454(10) . ?
N5 C4 1.454(10) 5_435 ?
N5 C4 1.454(10) 3_345 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N4 C5 1.497(12) . ?
N4 C6 1.483(7) 3_445 ?
N4 C6 1.483(7) . ?
N6 C5 1.452(11) 3_445 ?
N6 C5 1.452(11) 5_545 ?
N6 C5 1.452(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 N1 H1 118.5 5_545 . ?
C1 N1 H1 118.5 . . ?
C1 N1 C1 123.0(9) . 5_545 ?
N1 C1 S1 121.6(4) . . ?
N1 C1 S1 121.6(4) 3_445 . ?
N1 C1 N1 116.8(9) 3_445 . ?
C2 N2 H2 118.1 5_445 . ?
C2 N2 H2 118.1 . . ?
C2 N2 C2 123.7(9) . 5_445 ?
N2 C2 S2 121.9(4) . . ?
N2 C2 S2 121.9(4) 3_455 . ?
N2 C2 N2 116.2(9) . 3_455 ?
C3 N3 C3 109.2(10) 5_435 . ?
C3 N3 C4 108.7(5) 5_435 . ?
C3 N3 C4 108.7(5) . . ?
C4 N5 C4 108.9(6) 5_435 3_345 ?
C4 N5 C4 108.9(6) . 5_435 ?
C4 N5 C4 108.9(6) . 3_345 ?
N3 C3 N3 110.0(9) 3_345 . ?
N3 C3 H3A 109.7 3_345 . ?
N3 C3 H3A 109.7 . . ?
N3 C3 H3B 109.7 3_345 . ?
N3 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N3 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
N5 C4 N3 111.2(8) . . ?
N5 C4 H4A 109.4 . . ?
N5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 N4 C5 108.2(5) . . ?
C6 N4 C5 108.2(5) 3_445 . ?
C6 N4 C6 109.0(9) . 3_445 ?
C5 N6 C5 108.6(6) 5_545 . ?
C5 N6 C5 108.6(6) 5_545 3_445 ?
C5 N6 C5 108.6(6) 3_445 . ?
N4 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
N6 C5 N4 112.1(8) . . ?
N6 C5 H5A 109.2 . . ?
N6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N4 C6 N4 110.6(9) . 5_545 ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6A 109.5 5_545 . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6B 109.5 5_545 . ?
H6A C6 H6B 108.1 . . ?

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
N1 H1 N3 0.88 2.00 2.863(11) 165.5 . yes
N2 H2 N4 0.88 1.95 2.825(10) 174.1 . yes
C3 H3A S1 0.99 2.96 3.671(9) 129.8 5_545 yes
C3 H3A S1 0.99 2.96 3.671(9) 129.8 3_345 yes
C6 H6B S2 0.99 2.96 3.685(8) 130.9 . yes
C6 H6B S2 0.99 2.96 3.685(8) 130.9 3 yes

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 N1 C1 S1 172.2(5) 5_545 . . . ?
C1 N1 C1 N1 -7(2) 5_545 . . 3_445 ?
C2 N2 C2 S2 -174.0(6) 5_445 . . . ?
C2 N2 C2 N2 3(2) 5_445 . . 3_455 ?
C3 N3 C3 N3 59.6(11) 5_435 . . 3_345 ?
C3 N3 C4 N5 -59.4(5) 5_435 . . . ?
C3 N3 C4 N5 59.4(5) . . . . ?
C4 N3 C3 N3 -58.9(9) . . . 3_345 ?
C4 N5 C4 N3 59.3(7) 5_435 . . . ?
C4 N5 C4 N3 -59.3(7) 3_345 . . . ?
C5 N4 C6 N4 -58.3(9) . . . 5_545 ?
C5 N6 C5 N4 -59.0(7) 5_545 . . . ?
C5 N6 C5 N4 59.0(7) 3_445 . . . ?
C6 N4 C5 N6 -59.0(5) 3_445 . . . ?
C6 N4 C5 N6 59.0(5) . . . . ?
C6 N4 C6 N4 59.2(11) 3_445 . . 5_545 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(4)
2 -0.0(4)

