# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1508499'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'N,N?-Bis(4-Trifluoromethylthiobenzyl)naphthalene-1,4,5,8-tetracarboxylic acid diimide (NTCDI--BSCF3)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N O S'
_chemical_formula_weight         94.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.943(11)
_cell_length_b                   4.6447(17)
_cell_length_c                   14.264(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.415(17)
_cell_angle_gamma                90.00
_cell_volume                     1308.7(11)
_cell_formula_units_Z            15
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             705
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7598
_diffrn_reflns_av_R_equivalents  0.1270
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.03
_diffrn_reflns_theta_max         25.27
_reflns_number_total             2304
_reflns_number_gt                1618
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.36(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2304
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2975
_refine_ls_wR_factor_gt          0.2120
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11608(7) 0.4617(3) -0.00464(9) 0.0879(7) Uani 1 1 d . . .
N1 N 0.34293(14) -0.2990(7) 0.35694(19) 0.0520(9) Uani 1 1 d . . .
C2 C 0.46832(17) -0.0584(7) 0.4710(2) 0.0458(9) Uani 1 1 d . . .
C3 C 0.46589(16) -0.2568(8) 0.3949(2) 0.0484(9) Uani 1 1 d . . .
O4 O 0.29102(15) -0.0389(8) 0.4449(2) 0.0759(10) Uani 1 1 d . . .
C5 C 0.27578(19) -0.4166(9) 0.2961(3) 0.0554(10) Uani 1 1 d . . .
H5A H 0.2505 -0.4695 0.3395 0.067 Uiso 1 1 calc R . .
H5B H 0.2824 -0.5893 0.2622 0.067 Uiso 1 1 calc R . .
C6 C 0.23532(17) -0.2013(8) 0.2203(2) 0.0518(9) Uani 1 1 d . . .
F7 F 0.02686(16) 0.0602(8) -0.0815(3) 0.1098(12) Uani 1 1 d . . .
F8 F 0.02953(18) 0.4172(7) -0.1761(2) 0.1143(13) Uani 1 1 d . . .
C9 C 0.41355(18) 0.2121(9) 0.5675(2) 0.0581(11) Uani 1 1 d . . .
H9A H 0.3746 0.2621 0.5813 0.070 Uiso 1 1 calc R . .
C10 C 0.40935(17) 0.0190(8) 0.4910(2) 0.0493(9) Uani 1 1 d . . .
C11 C 0.34370(18) -0.0999(9) 0.4311(2) 0.0549(10) Uani 1 1 d . . .
C12 C 0.52398(18) -0.3320(10) 0.3761(2) 0.0591(11) Uani 1 1 d . . .
H12A H 0.5219 -0.4629 0.3258 0.071 Uiso 1 1 calc R . .
O13 O 0.39635(15) -0.5678(8) 0.2722(2) 0.0836(11) Uani 1 1 d . . .
C14 C 0.40027(19) -0.3860(9) 0.3353(3) 0.0574(10) Uani 1 1 d . . .
C15 C 0.2201(2) 0.0798(9) 0.0725(3) 0.0642(11) Uani 1 1 d . . .
H15A H 0.2354 0.1370 0.0212 0.077 Uiso 1 1 calc R . .
C16 C 0.17643(19) -0.0853(9) 0.2271(3) 0.0604(11) Uani 1 1 d . . .
H16A H 0.1618 -0.1376 0.2796 0.073 Uiso 1 1 calc R . .
C17 C 0.16104(19) 0.1924(9) 0.0798(3) 0.0629(11) Uani 1 1 d . . .
F18 F 0.1033(2) 0.0843(8) -0.1437(2) 0.1105(12) Uani 1 1 d . . .
C19 C 0.1389(2) 0.1078(10) 0.1567(3) 0.0654(11) Uani 1 1 d . . .
H19A H 0.0987 0.1812 0.1610 0.078 Uiso 1 1 calc R . .
C20 C 0.25690(18) -0.1200(9) 0.1425(3) 0.0577(10) Uani 1 1 d . . .
H20A H 0.2962 -0.1993 0.1369 0.069 Uiso 1 1 calc R . .
C21 C 0.0667(2) 0.2457(10) -0.1033(3) 0.0709(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.1053(12) 0.0469(9) 0.0752(9) -0.0011(5) -0.0185(7) 0.0006(5)
N1 0.0547(17) 0.0469(19) 0.0482(15) -0.0050(13) 0.0088(12) -0.0017(13)
C2 0.0558(19) 0.0382(19) 0.0410(16) 0.0020(13) 0.0129(14) 0.0016(14)
C3 0.0558(19) 0.047(2) 0.0389(16) -0.0039(14) 0.0106(13) 0.0013(15)
O4 0.0589(17) 0.101(3) 0.0690(18) -0.0166(16) 0.0231(14) -0.0026(15)
C5 0.060(2) 0.047(2) 0.0530(19) -0.0006(16) 0.0104(16) -0.0078(16)
C6 0.0550(19) 0.045(2) 0.0497(17) -0.0010(15) 0.0093(14) -0.0056(15)
F7 0.086(2) 0.111(3) 0.111(2) 0.0116(19) 0.0047(17) -0.0347(17)
F8 0.135(3) 0.081(2) 0.0765(18) 0.0115(15) -0.0320(17) 0.0089(17)
C9 0.060(2) 0.066(3) 0.0466(18) -0.0080(17) 0.0166(15) 0.0103(18)
C10 0.054(2) 0.049(2) 0.0418(17) 0.0025(14) 0.0116(14) 0.0033(15)
C11 0.061(2) 0.056(2) 0.0452(17) 0.0017(15) 0.0145(15) 0.0022(17)
C12 0.065(2) 0.065(3) 0.0446(17) -0.0077(16) 0.0145(15) 0.0070(18)
O13 0.073(2) 0.096(3) 0.0725(19) -0.0413(17) 0.0123(15) 0.0000(16)
C14 0.063(2) 0.057(3) 0.0462(17) -0.0051(16) 0.0095(15) -0.0006(17)
C15 0.072(2) 0.060(3) 0.056(2) 0.0048(18) 0.0154(18) -0.0098(19)
C16 0.060(2) 0.064(3) 0.056(2) -0.0059(18) 0.0175(16) -0.0056(18)
C17 0.065(2) 0.052(2) 0.056(2) -0.0057(18) -0.0007(16) -0.0057(18)
F18 0.143(3) 0.109(3) 0.0743(18) -0.0104(16) 0.0299(19) 0.020(2)
C19 0.060(2) 0.063(3) 0.065(2) -0.003(2) 0.0111(17) 0.0067(18)
C20 0.056(2) 0.064(3) 0.0515(19) 0.0006(17) 0.0154(15) -0.0018(17)
C21 0.076(3) 0.059(3) 0.063(2) 0.011(2) 0.004(2) 0.002(2)

_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 C21 1.757(5) . ?
S1 C17 1.774(4) . ?
N1 C14 1.396(5) . ?
N1 C11 1.402(5) . ?
N1 C5 1.489(4) . ?
C2 C10 1.403(5) . ?
C2 C3 1.412(5) . ?
C2 C2 1.417(7) 3_656 ?
C3 C12 1.375(5) . ?
C3 C14 1.482(5) . ?
O4 C11 1.216(4) . ?
C5 C6 1.509(5) . ?
C6 C16 1.378(5) . ?
C6 C20 1.382(5) . ?
F7 C21 1.307(5) . ?
F8 C21 1.335(5) . ?
C9 C10 1.393(5) . ?
C9 C12 1.403(5) 3_656 ?
C10 C11 1.464(5) . ?
C12 C9 1.403(5) 3_656 ?
O13 C14 1.217(5) . ?
C15 C17 1.379(6) . ?
C15 C20 1.393(6) . ?
C16 C19 1.381(6) . ?
C17 C19 1.382(6) . ?
F18 C21 1.334(6) . ?

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
C21 S1 C17 100.3(2) . . ?
C14 N1 C11 124.3(3) . . ?
C14 N1 C5 118.7(3) . . ?
C11 N1 C5 117.0(3) . . ?
C10 C2 C3 120.9(3) . . ?
C10 C2 C2 120.0(4) . 3_656 ?
C3 C2 C2 119.0(4) . 3_656 ?
C12 C3 C2 120.5(3) . . ?
C12 C3 C14 119.8(3) . . ?
C2 C3 C14 119.7(3) . . ?
N1 C5 C6 111.8(3) . . ?
C16 C6 C20 119.2(3) . . ?
C16 C6 C5 120.7(3) . . ?
C20 C6 C5 120.0(3) . . ?
C10 C9 C12 120.6(3) . 3_656 ?
C9 C10 C2 119.6(3) . . ?
C9 C10 C11 120.1(3) . . ?
C2 C10 C11 120.3(3) . . ?
O4 C11 N1 119.5(3) . . ?
O4 C11 C10 123.0(3) . . ?
N1 C11 C10 117.5(3) . . ?
C3 C12 C9 120.3(3) . 3_656 ?
O13 C14 N1 120.9(3) . . ?
O13 C14 C3 121.8(3) . . ?
N1 C14 C3 117.2(3) . . ?
C17 C15 C20 119.7(4) . . ?
C6 C16 C19 120.6(4) . . ?
C15 C17 C19 119.9(4) . . ?
C15 C17 S1 120.2(3) . . ?
C19 C17 S1 119.8(3) . . ?
C16 C19 C17 120.1(4) . . ?
C6 C20 C15 120.5(4) . . ?
F7 C21 F18 103.7(4) . . ?
F7 C21 F8 109.0(4) . . ?
F18 C21 F8 105.6(4) . . ?
F7 C21 S1 116.0(3) . . ?
F18 C21 S1 113.4(3) . . ?
F8 C21 S1 108.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.102
_exptl_crystal_recrystallization_method Sublimation
