# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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. 
# 
#######################################################################

data_Anthracene-DTTCNQ
_database_code_depnum_ccdc_archive 'CCDC 1915403'
loop_
_audit_author_name
_audit_author_address
'Hui Jiang'
;School of Materials Science and Engineering, Nanyang Technological University
Singapore
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_chemical_name_systematic        Anthracene-DTTCNQ
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H14 N4 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         494.57

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.3775(4)
_cell_length_b                   9.3783(6)
_cell_length_c                   9.4318(6)
_cell_angle_alpha                61.214(2)
_cell_angle_beta                 89.717(2)
_cell_angle_gamma                73.611(2)
_cell_volume                     542.00(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6751
_cell_measurement_theta_min      2.4943
_cell_measurement_theta_max      30.3769
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'Dark Green/ Black'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             254

_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            27227
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3315
_reflns_number_gt                2520
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1415
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.110
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     191
_refine_ls_number_restraints     158
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.6906P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5972(3) 0.1628(3) 0.9594(3) 0.0186(4) Uani d . . . 1.0 . .
C C2 0.6652(3) 0.1941(3) 0.8076(2) 0.0150(4) Uani d . . . 1.0 . .
C C3 0.8222(3) 0.0495(3) 0.8314(2) 0.0173(4) Uani d . . . 1.0 . .
C C4 0.5886(3) 0.3423(3) 0.6588(2) 0.0137(4) Uani d . . . 1.0 . .
C C5 0.4526(3) 0.4955(3) 0.6462(2) 0.0137(4) Uani d U . D 1.0 . .
C C6 0.3661(3) 0.6445(3) 0.4963(2) 0.0135(4) Uani d U . D 1.0 . .
C C7 0.2493(19) 0.7797(16) 0.5210(17) 0.0168(17) Uani d U P D 0.598(3) A 1
H H7 0.1812 0.8916 0.4343 0.02 Uiso calc U P R 0.598(3) A 1
C C8 0.2471(8) 0.7296(6) 0.6817(6) 0.0161(10) Uani d U P D 0.598(3) A 1
H H8 0.176 0.8023 0.72 0.019 Uiso calc U P R 0.598(3) A 1
S S1 0.3857(5) 0.5223(4) 0.8078(3) 0.0161(4) Uani d U P D 0.598(3) A 1
C C7A 0.404(3) 0.523(2) 0.7820(16) 0.014(2) Uani d U P D 0.402(3) A 2
H H7A 0.4533 0.4402 0.8938 0.017 Uiso calc U P R 0.402(3) A 2
C C8A 0.2782(13) 0.6835(10) 0.7278(9) 0.0147(13) Uani d U P D 0.402(3) A 2
H H8A 0.2272 0.7236 0.7995 0.018 Uiso calc U P R 0.402(3) A 2
S S1A 0.2212(7) 0.8050(5) 0.5209(6) 0.0160(6) Uani d U P D 0.402(3) A 2
C C9 0.0393(3) 0.5059(3) 0.3509(2) 0.0158(4) Uani d . . . 1.0 . .
C C10 0.0823(3) 0.5061(3) 0.2028(3) 0.0187(4) Uani d . . . 1.0 . .
H H10 0.0275 0.6072 0.1002 0.022 Uiso calc U . R 1.0 . .
C C11 0.2014(3) 0.3623(3) 0.2076(3) 0.0203(5) Uani d . . . 1.0 . .
H H11 0.2276 0.3638 0.1083 0.024 Uiso calc U . R 1.0 . .
C C12 0.2860(3) 0.2111(3) 0.3593(3) 0.0206(5) Uani d . . . 1.0 . .
H H12 0.3697 0.1125 0.3607 0.025 Uiso calc U . R 1.0 . .
C C13 0.2488(3) 0.2052(3) 0.5030(3) 0.0190(4) Uani d . . . 1.0 . .
H H13 0.3058 0.1022 0.6037 0.023 Uiso calc U . R 1.0 . .
C C14 0.1251(3) 0.3518(3) 0.5044(3) 0.0159(4) Uani d . . . 1.0 . .
C C15 0.0833(3) 0.3499(3) 0.6498(3) 0.0168(4) Uani d . . . 1.0 . .
H H15 0.1396 0.2481 0.7516 0.02 Uiso calc U . R 1.0 . .
N N1 0.5475(3) 0.1246(3) 1.0841(2) 0.0258(5) Uani d . . . 1.0 . .
N N2 0.9515(3) -0.0686(3) 0.8623(2) 0.0249(4) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.145(3) ?
C1 C2 . 1.435(3) ?
C2 C4 . 1.381(3) ?
C2 C3 . 1.433(3) ?
C3 N2 . 1.148(3) ?
C4 C5 . 1.452(3) ?
C4 C6 2_666 1.453(3) ?
C5 C6 . 1.401(3) ?
C5 C7A . 1.447(12) ?
C5 S1 . 1.709(3) ?
C6 C7 . 1.439(10) ?
C6 C4 2_666 1.453(3) ?
C6 S1A . 1.700(4) ?
C7 C8 . 1.356(14) ?
C7 H7 . 0.95 ?
C8 S1 . 1.704(5) ?
C8 H8 . 0.95 ?
C7A C8A . 1.367(16) ?
C7A H7A . 0.95 ?
C8A S1A . 1.697(8) ?
C8A H8A . 0.95 ?
C9 C15 2_566 1.396(3) ?
C9 C10 . 1.430(3) ?
C9 C14 . 1.436(3) ?
C10 C11 . 1.366(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.415(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.360(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.425(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.398(3) ?
C15 C9 2_566 1.396(3) ?
C15 H15 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 174.7(2) ?
C4 C2 C3 . . 124.69(19) ?
C4 C2 C1 . . 124.68(19) ?
C3 C2 C1 . . 110.63(18) ?
N2 C3 C2 . . 174.8(2) ?
C2 C4 C5 . . 122.10(18) ?
C2 C4 C6 . 2_666 122.76(19) ?
C5 C4 C6 . 2_666 115.11(17) ?
C6 C5 C7A . . 111.0(7) ?
C6 C5 C4 . . 123.11(18) ?
C7A C5 C4 . . 125.6(7) ?
C6 C5 S1 . . 111.46(17) ?
C4 C5 S1 . . 125.37(17) ?
C5 C6 C7 . . 111.0(6) ?
C5 C6 C4 . 2_666 121.75(18) ?
C7 C6 C4 . 2_666 126.9(6) ?
C5 C6 S1A . . 112.3(2) ?
C4 C6 S1A 2_666 . 125.8(2) ?
C8 C7 C6 . . 112.5(9) ?
C8 C7 H7 . . 123.8 ?
C6 C7 H7 . . 123.8 ?
C7 C8 S1 . . 112.7(6) ?
C7 C8 H8 . . 123.6 ?
S1 C8 H8 . . 123.6 ?
C8 S1 C5 . . 92.3(3) ?
C8A C7A C5 . . 110.9(11) ?
C8A C7A H7A . . 124.5 ?
C5 C7A H7A . . 124.5 ?
C7A C8A S1A . . 113.9(8) ?
C7A C8A H8A . . 123.0 ?
S1A C8A H8A . . 123.0 ?
C8A S1A C6 . . 91.7(4) ?
C15 C9 C10 2_566 . 121.97(19) ?
C15 C9 C14 2_566 . 119.45(19) ?
C10 C9 C14 . . 118.58(19) ?
C11 C10 C9 . . 120.6(2) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.6(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 120.7(2) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C15 C14 C13 . . 122.2(2) ?
C15 C14 C9 . . 119.04(19) ?
C13 C14 C9 . . 118.77(19) ?
C9 C15 C14 2_566 . 121.51(19) ?
C9 C15 H15 2_566 . 119.2 ?
C14 C15 H15 . . 119.2 ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
