# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a_b
_database_code_depnum_ccdc_archive 'CCDC 2089461'
loop_
_audit_author_name
_audit_author_address
'Canglei Yang'
;Nanjing University of Posts and Telecommunications
China
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-08-10
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6225)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Form 1'
_chemical_formula_moiety         'C16 H4 N4 S2, C16 H10'
_chemical_formula_sum            'C32 H14 N4 S2'
_chemical_formula_weight         518.59
_chemical_melting_point          300
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4924(4)
_cell_length_b                   9.4682(5)
_cell_length_c                   9.6821(5)
_cell_angle_alpha                112.930(2)
_cell_angle_beta                 109.052(2)
_cell_angle_gamma                90.147(2)
_cell_volume                     591.24(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7251
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      5.13
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12390
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.644
_diffrn_reflns_theta_min         5.129
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1784
_reflns_number_total             2181
_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_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.084
_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)+(0.1317P)²+0.0583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2071
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Others
 Fixed Sof: C1(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
 C6(0.5) S1A(0.5) C1A(0.5) H1A(0.5) C1B(0.5) H1B(0.5) S1B(0.5) C7(0.5) H7(0.5)
 C8(0.5) H8(0.5) C9B(0.5) H9B(0.5) C16(0.5) C2A(0.5) C3A(0.5) H3A(0.5) C4A(0.5)
 H4A(0.5) C5A(0.5) H5A(0.5) C6A(0.5) C7A(0.5) H7A(0.5) C8A(0.5) H8A(0.5)
 C9A(0.5) H9A(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C1A(H1A), C1B(H1B), C7(H7), C8(H8), C9B(H9B),
 C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C9A(H9A)
4.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C16(C2A,C3A,C4A,C5A,C6A)
;
_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
N2 N 0.0365(4) 0.5526(3) 0.3250(4) 0.1206(10) Uani 1 1 d . . . . .
C1 C 0.4620(7) 0.0672(5) 0.9839(6) 0.078(2) Uani 0.5 1 d G . P A 1
C2 C 0.5103(7) 0.2191(6) 1.0997(5) 0.0799(16) Uani 0.5 1 d G . P A 1
C3 C 0.4363(7) 0.3385(4) 1.0603(7) 0.1023(19) Uani 0.5 1 d G . P A 1
H3 H 0.468587 0.440123 1.137709 0.123 Uiso 0.5 1 calc R U P A 1
C4 C 0.3140(8) 0.3060(6) 0.9050(8) 0.112(2) Uani 0.5 1 d G . P A 1
H4 H 0.264471 0.385828 0.878620 0.134 Uiso 0.5 1 calc R U P A 1
C5 C 0.2657(7) 0.1541(7) 0.7893(6) 0.111(3) Uani 0.5 1 d G . P A 1
H5 H 0.183868 0.132305 0.685395 0.133 Uiso 0.5 1 calc R U P A 1
C6 C 0.3397(6) 0.0347(5) 0.8287(6) 0.0856(14) Uani 0.5 1 d G . P A 1
S1A S 0.1344(5) -0.2936(5) 0.0421(6) 0.0853(8) Uani 0.5 1 d . . P B 1
C1A C 0.246(3) -0.049(3) 0.278(3) 0.083(4) Uani 0.5 1 d . . P B 1
H1A H 0.302747 0.023928 0.382904 0.099 Uiso 0.5 1 calc R U P B 1
C1B C 0.118(3) -0.271(2) 0.040(3) 0.112(6) Uani 0.5 1 d . . P B 2
H1B H 0.080295 -0.374254 -0.032398 0.134 Uiso 0.5 1 calc R U P B 2
S1B S 0.2755(7) -0.0224(6) 0.3070(6) 0.0829(9) Uani 0.5 1 d . . P B 2
N1 N 0.4072(4) 0.3315(4) 0.5499(3) 0.1191(10) Uani 1 1 d . . . . .
C7 C 0.2931(10) -0.1244(9) 0.7136(11) 0.0834(15) Uani 0.5 1 d . . P A 1
H7 H 0.211130 -0.151632 0.608581 0.100 Uiso 0.5 1 calc R U P A 1
C8 C 0.3759(18) -0.2398(13) 0.7648(17) 0.101(4) Uani 0.5 1 d . . P A 1
H8 H 0.340787 -0.341793 0.688257 0.121 Uiso 0.5 1 calc R U P A 1
C9B C 0.236(3) -0.218(3) 0.1906(15) 0.089(4) Uani 0.5 1 d . . P B 2
H9B H 0.296173 -0.285430 0.232644 0.106 Uiso 0.5 1 calc R U P B 2
C10 C 0.0575(3) -0.1393(3) 0.0068(3) 0.0732(6) Uani 1 1 d . . . . .
C11 C 0.1277(3) -0.0006(3) 0.1431(3) 0.0733(6) Uani 1 1 d . . . . .
C12 C 0.0759(3) 0.1476(3) 0.1462(3) 0.0739(6) Uani 1 1 d . . . . .
C13 C 0.1439(3) 0.2847(3) 0.2818(3) 0.0813(7) Uani 1 1 d . . . . .
C14 C 0.2898(4) 0.3034(4) 0.4294(4) 0.0930(8) Uani 1 1 d . . . . .
C15 C 0.0798(4) 0.4314(3) 0.2974(4) 0.0920(8) Uani 1 1 d . . . . .
C16 C 0.4431(7) 0.0225(7) 0.9422(6) 0.0777(18) Uani 0.5 1 d G . P C 2
C2A C 0.3491(8) -0.0926(5) 0.7893(7) 0.107(3) Uani 0.5 1 d G . P C 2
C3A C 0.2324(7) -0.0538(8) 0.6688(5) 0.110(2) Uani 0.5 1 d G . P C 2
H3A H 0.169546 -0.130792 0.566537 0.131 Uiso 0.5 1 calc R U P C 2
C4A C 0.2098(7) 0.1002(9) 0.7010(7) 0.119(3) Uani 0.5 1 d G . P C 2
H4A H 0.131752 0.126153 0.620351 0.143 Uiso 0.5 1 calc R U P C 2
C5A C 0.3038(8) 0.2153(6) 0.8538(8) 0.107(3) Uani 0.5 1 d G . P C 2
H5A H 0.288667 0.318259 0.875402 0.128 Uiso 0.5 1 calc R U P C 2
C6A C 0.4205(6) 0.1764(6) 0.9744(5) 0.0951(15) Uani 0.5 1 d G . P C 2
C7A C 0.5208(15) 0.2984(12) 1.1372(13) 0.118(3) Uani 0.5 1 d . . P C 2
H7A H 0.509498 0.402485 1.161925 0.142 Uiso 0.5 1 calc R U P C 2
C8A C 0.644(2) 0.2449(18) 1.2625(14) 0.115(5) Uani 0.5 1 d . . P C 2
H8A H 0.709452 0.313819 1.368173 0.138 Uiso 0.5 1 calc R U P C 2
C9A C 0.262(3) -0.188(3) 0.2399(17) 0.082(3) Uani 0.5 1 d . . P B 1
H9A H 0.333582 -0.228958 0.309975 0.098 Uiso 0.5 1 calc R U P B 1


_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
N2 C15 1.146(4) . ?
C1 C1 1.496(6) 2_657 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 C8 1.247(15) 2_657 ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 C7 1.438(9) . ?
S1A C10 1.688(4) . ?
S1A C9A 1.699(14) . ?
C1A H1A 0.9300 . ?
C1A C11 1.550(19) . ?
C1A C9A 1.24(3) . ?
C1B H1B 0.9300 . ?
C1B C9B 1.32(2) . ?
C1B C10 1.438(16) . ?
S1B C9B 1.71(2) . ?
S1B C11 1.702(4) . ?
N1 C14 1.137(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.431(12) . ?
C8 H8 0.9300 . ?
C9B H9B 0.9300 . ?
C10 C11 1.392(4) . ?
C10 C12 1.464(3) 2 ?
C11 C12 1.448(3) . ?
C12 C13 1.378(4) . ?
C13 C14 1.432(4) . ?
C13 C15 1.439(4) . ?
C16 C16 1.383(7) 2_657 ?
C16 C2A 1.3900 . ?
C16 C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A C8A 1.337(17) 2_657 ?
C3A H3A 0.9300 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.3900 . ?
C6A C7A 1.479(11) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.53(2) . ?
C8A H8A 0.9300 . ?
C9A H9A 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
C2 C1 C1 123.3(5) . 2_657 ?
C2 C1 C6 120.0 . . ?
C6 C1 C1 116.7(5) . 2_657 ?
C1 C2 C3 120.0 . . ?
C8 C2 C1 116.3(6) 2_657 . ?
C8 C2 C3 123.6(6) 2_657 . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 117.9(5) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 122.1(5) . . ?
C10 S1A C9A 94.8(7) . . ?
C11 C1A H1A 121.1 . . ?
C9A C1A H1A 121.1 . . ?
C9A C1A C11 117.8(16) . . ?
C9B C1B H1B 126.1 . . ?
C9B C1B C10 107.8(17) . . ?
C10 C1B H1B 126.1 . . ?
C11 S1B C9B 87.7(5) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.3(9) . . ?
C8 C7 H7 120.8 . . ?
C2 C8 C7 127.4(11) 2_657 . ?
C2 C8 H8 116.3 2_657 . ?
C7 C8 H8 116.3 . . ?
C1B C9B S1B 118.7(16) . . ?
C1B C9B H9B 120.6 . . ?
S1B C9B H9B 120.6 . . ?
C11 C10 S1A 112.4(2) . . ?
C11 C10 C1B 112.0(9) . . ?
C11 C10 C12 122.6(2) . 2 ?
C12 C10 S1A 124.9(3) 2 . ?
C10 C11 C1A 104.6(9) . . ?
C10 C11 S1B 113.6(2) . . ?
C10 C11 C12 123.2(2) . . ?
C12 C11 C1A 131.9(9) . . ?
C12 C11 S1B 123.2(3) . . ?
C11 C12 C10 114.2(2) . 2 ?
C13 C12 C10 122.6(2) . 2 ?
C13 C12 C11 123.1(2) . . ?
C12 C13 C14 125.3(2) . . ?
C12 C13 C15 125.5(2) . . ?
C14 C13 C15 109.3(2) . . ?
N1 C14 C13 174.1(3) . . ?
N2 C15 C13 173.6(3) . . ?
C16 C16 C2A 117.7(6) 2_657 . ?
C16 C16 C6A 122.3(6) 2_657 . ?
C2A C16 C6A 120.0 . . ?
C16 C2A C3A 120.0 . . ?
C8A C2A C16 127.8(8) 2_657 . ?
C8A C2A C3A 112.2(8) 2_657 . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C16 C6A C7A 119.8(6) . . ?
C5A C6A C16 120.0 . . ?
C5A C6A C7A 120.2(6) . . ?
C6A C7A H7A 121.7 . . ?
C6A C7A C8A 116.6(9) . . ?
C8A C7A H7A 121.7 . . ?
C2A C8A C7A 115.8(8) 2_657 . ?
C2A C8A H8A 122.1 2_657 . ?
C7A C8A H8A 122.1 . . ?
S1A C9A H9A 124.9 . . ?
C1A C9A S1A 110.3(13) . . ?
C1A C9A H9A 124.9 . . ?

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 C3 179.0(7) 2_657 . . . ?
C1 C1 C2 C8 0.6(8) 2_657 . . 2_657 ?
C1 C1 C6 C5 -179.0(6) 2_657 . . . ?
C1 C1 C6 C7 1.4(7) 2_657 . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C6 C7 C8 -0.4(9) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 -179.6(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 179.6(4) . . . . ?
C5 C6 C7 C8 180.0(7) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C2 C8 -178.4(8) . . . 2_657 ?
C6 C7 C8 C2 -1.4(17) . . . 2_657 ?
S1A C10 C11 C1A -2.2(9) . . . . ?
S1A C10 C11 C12 -177.06(19) . . . . ?
C1A C11 C12 C10 -173.2(11) . . . 2 ?
C1A C11 C12 C13 6.0(11) . . . . ?
C1B C10 C11 S1B 3.6(8) . . . . ?
C1B C10 C11 C12 -174.8(8) . . . . ?
S1B C11 C12 C10 -178.2(3) . . . 2 ?
S1B C11 C12 C13 1.0(4) . . . . ?
C8 C2 C3 C4 178.3(8) 2_657 . . . ?
C9B C1B C10 C11 -4.5(17) . . . . ?
C9B C1B C10 C12 -179.1(13) . . . 2 ?
C9B S1B C11 C10 -1.3(8) . . . . ?
C9B S1B C11 C12 177.1(8) . . . . ?
C10 S1A C9A C1A 1.1(17) . . . . ?
C10 C1B C9B S1B 4(2) . . . . ?
C10 C11 C12 C10 0.0(3) . . . 2 ?
C10 C11 C12 C13 179.3(2) . . . . ?
C10 C12 C13 C14 -172.7(2) 2 . . . ?
C10 C12 C13 C15 7.2(4) 2 . . . ?
C11 C1A C9A S1A -3(2) . . . . ?
C11 S1B C9B C1B -1.6(19) . . . . ?
C11 C12 C13 C14 8.1(4) . . . . ?
C11 C12 C13 C15 -171.9(2) . . . . ?
C12 C10 C11 C1A 174.8(8) 2 . . . ?
C12 C10 C11 S1B 178.4(2) 2 . . . ?
C12 C10 C11 C12 0.0(4) 2 . . . ?
C16 C16 C2A C3A 179.8(7) 2_657 . . . ?
C16 C16 C2A C8A -1.0(9) 2_657 . . 2_657 ?
C16 C16 C6A C5A -179.8(7) 2_657 . . . ?
C16 C16 C6A C7A 0.2(8) 2_657 . . . ?
C16 C2A C3A C4A 0.0 . . . . ?
C16 C6A C7A C8A -0.8(11) . . . . ?
C2A C16 C6A C5A 0.0 . . . . ?
C2A C16 C6A C7A 180.0(5) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C16 0.0 . . . . ?
C4A C5A C6A C7A -180.0(5) . . . . ?
C5A C6A C7A C8A 179.2(8) . . . . ?
C6A C16 C2A C3A 0.0 . . . . ?
C6A C16 C2A C8A 179.3(9) . . . 2_657 ?
C6A C7A C8A C2A 1.3(16) . . . 2_657 ?
C8A C2A C3A C4A -179.4(8) 2_657 . . . ?
C9A S1A C10 C11 0.9(8) . . . . ?
C9A S1A C10 C12 -176.0(7) . . . 2 ?
C9A C1A C11 C10 3(2) . . . . ?
C9A C1A C11 C12 177.5(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20191211zjycl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2089463'
loop_
_audit_author_name
_audit_author_address
'Canglei Yang'
;Nanjing University of Posts and Telecommunications
China
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-08-10
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6225)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H4 N4 S2, C16 H10'
_chemical_formula_sum            'C32 H12 N4 S2'
_chemical_formula_weight         516.58
_chemical_melting_point          300
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.551(5)
_cell_length_b                   9.095(6)
_cell_length_c                   9.799(7)
_cell_angle_alpha                67.642(13)
_cell_angle_beta                 86.816(15)
_cell_angle_gamma                74.351(14)
_cell_volume                     598.5(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3174
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      292.11
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1172
_reflns_number_total             2034
_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_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      0.991
_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)+(0.1219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2149
_refine_ls_wR_factor_ref         0.2339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C15A)=Sof(H15A)=Sof(S1B)=Sof(H7B)=1-FVAR(1)
 Sof(S1A)=Sof(C15B)=Sof(H15B)=Sof(H7A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C15A(H15A), C15B(H15B), C7(H7A), C7(H7B), C00I(H00I), C8(H8), C11(H11),
 C12(H12), C14(H14)
;
_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
S1A S 0.7628(4) 0.6898(3) 0.4610(3) 0.0483(9) Uani 0.630(6) 1 d . . P A 1
C15A C 0.733(4) 0.739(3) 0.460(3) 0.065(6) Uani 0.370(6) 1 d . . P A 2
H15A H 0.801527 0.640361 0.530270 0.078 Uiso 0.370(6) 1 calc R U P A 2
S1B S 0.6279(19) 0.9555(13) 0.2074(9) 0.057(3) Uani 0.370(6) 1 d . . P A 2
C15B C 0.618(4) 0.951(3) 0.234(3) 0.056(4) Uani 0.630(6) 1 d . . P A 1
H15B H 0.587423 1.020068 0.135528 0.067 Uiso 0.630(6) 1 calc R U P A 1
N1 N 0.5470(7) 0.6785(6) 1.0362(5) 0.0785(15) Uani 1 1 d . . . . .
N2 N 0.8764(7) 0.4476(6) 0.7916(5) 0.0882(17) Uani 1 1 d . . . . .
C1 C 0.5807(7) 0.7060(6) 0.9152(6) 0.0540(12) Uani 1 1 d . . . . .
C2 C 0.7696(7) 0.5694(6) 0.7757(5) 0.0559(13) Uani 1 1 d . . . . .
C3 C 0.6362(6) 0.7201(5) 0.7683(5) 0.0472(11) Uani 1 1 d . . . . .
C4 C 0.5718(6) 0.8557(5) 0.6390(5) 0.0381(9) Uani 1 1 d . . . . .
C5 C 0.6230(5) 0.8560(5) 0.4932(5) 0.0372(9) Uani 1 1 d . . . . .
C6 C 0.5546(5) 0.9909(5) 0.3619(5) 0.0385(10) Uani 1 1 d . . . . .
C7 C 0.7361(8) 0.7823(7) 0.2875(6) 0.0664(15) Uani 1 1 d . . . . .
H7A H 0.792592 0.732365 0.223424 0.080 Uiso 0.630(6) 1 calc R U P A 1
H7B H 0.796857 0.710079 0.243014 0.080 Uiso 0.370(6) 1 calc R U P A 2
C00I C -0.0374(9) 0.8849(8) 0.8808(7) 0.0798(17) Uani 1 1 d . . . . .
H00I H -0.046174 0.853634 0.982467 0.096 Uiso 1 1 calc R U . . .
C8 C 0.1371(8) 0.9614(8) 0.2099(6) 0.0736(16) Uani 1 1 d . . . . .
H8 H 0.212614 0.890219 0.170003 0.088 Uiso 1 1 calc R U . . .
C9 C 0.0100(6) 1.0210(6) 0.4229(5) 0.0477(11) Uani 1 1 d . . . . .
C10 C 0.1242(7) 0.9111(7) 0.3661(6) 0.0575(12) Uani 1 1 d . . . . .
C11 C 0.2231(7) 0.7513(7) 0.4661(7) 0.0681(13) Uani 1 1 d . . . . .
H11 H 0.298830 0.677382 0.429200 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2081(7) 0.7062(7) 0.6137(6) 0.0637(13) Uani 1 1 d . . . . .
H12 H 0.274381 0.601540 0.676070 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0920(7) 0.8159(7) 0.6776(6) 0.0590(12) Uani 1 1 d . . . . .
C14 C 0.0773(9) 0.7728(8) 0.8263(6) 0.0736(15) Uani 1 1 d . . . . .
H14 H 0.143118 0.669340 0.891288 0.088 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
S1A C5 1.722(5) . ?
S1A C7 1.580(7) . ?
C15A H15A 0.9300 . ?
C15A C5 1.30(2) . ?
C15A C7 1.59(3) . ?
S1B C6 1.698(10) . ?
S1B C7 1.484(12) . ?
C15B H15B 0.9300 . ?
C15B C6 1.46(2) . ?
C15B C7 1.46(3) . ?
N1 C1 1.143(6) . ?
N2 C2 1.141(6) . ?
C1 C3 1.445(7) . ?
C2 C3 1.444(7) . ?
C3 C4 1.385(6) . ?
C4 C5 1.458(6) . ?
C4 C6 1.460(6) 2_676 ?
C5 C6 1.399(6) . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C8 1.369(8) 2_576 ?
C00I C14 1.400(9) . ?
C8 H8 0.9300 . ?
C8 C10 1.428(8) . ?
C9 C9 1.421(9) 2_576 ?
C9 C10 1.399(7) . ?
C9 C13 1.456(7) 2_576 ?
C10 C11 1.429(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.352(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.449(8) . ?
C13 C14 1.364(8) . ?
C14 H14 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
C7 S1A C5 93.2(3) . . ?
C5 C15A H15A 123.7 . . ?
C5 C15A C7 112.5(17) . . ?
C7 C15A H15A 123.7 . . ?
C7 S1B C6 95.3(5) . . ?
C6 C15B H15B 126.0 . . ?
C6 C15B C7 107.9(15) . . ?
C7 C15B H15B 126.0 . . ?
N1 C1 C3 173.0(5) . . ?
N2 C2 C3 175.4(6) . . ?
C2 C3 C1 109.5(4) . . ?
C4 C3 C1 125.9(4) . . ?
C4 C3 C2 124.6(5) . . ?
C3 C4 C5 122.8(4) . . ?
C3 C4 C6 122.5(4) . 2_676 ?
C5 C4 C6 114.7(4) . 2_676 ?
C15A C5 C4 128.4(12) . . ?
C15A C5 C6 108.5(12) . . ?
C4 C5 S1A 124.7(3) . . ?
C6 C5 S1A 112.1(3) . . ?
C6 C5 C4 123.1(4) . . ?
C15B C6 C4 127.0(11) . 2_676 ?
C4 C6 S1B 124.3(4) 2_676 . ?
C5 C6 S1B 113.6(4) . . ?
C5 C6 C15B 110.8(11) . . ?
C5 C6 C4 122.2(4) . 2_676 ?
S1A C7 H7A 122.0 . . ?
C15A C7 H7B 125.1 . . ?
S1B C7 C15A 109.8(9) . . ?
S1B C7 H7B 125.1 . . ?
C15B C7 S1A 115.9(10) . . ?
C15B C7 H7A 122.0 . . ?
C8 C00I H00I 118.8 2_576 . ?
C8 C00I C14 122.5(6) 2_576 . ?
C14 C00I H00I 118.8 . . ?
C00I C8 H8 120.3 2_576 . ?
C00I C8 C10 119.5(6) 2_576 . ?
C10 C8 H8 120.3 . . ?
C9 C9 C13 118.3(6) 2_576 2_576 ?
C10 C9 C9 122.0(6) . 2_576 ?
C10 C9 C13 119.7(5) . 2_576 ?
C8 C10 C11 122.0(6) . . ?
C9 C10 C8 119.0(5) . . ?
C9 C10 C11 119.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.0(5) . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C9 117.7(5) . 2_576 ?
C14 C13 C9 119.6(6) . 2_576 ?
C14 C13 C12 122.7(5) . . ?
C00I C14 H14 120.1 . . ?
C13 C14 C00I 119.8(6) . . ?
C13 C14 H14 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
