# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_dtb
_database_code_depnum_ccdc_archive 'CCDC 1503592'
_audit_update_record             
;
2016-09-09 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT041_dtb                 
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Some hydrogen position with partial occupancy was not found by the analysis of Fourier maps during the refinement 
;
_vrf_PLAT052_dtb                 
;
PROBLEM: Info on Absorption Correction Method   Not Given     Please Do !
RESPONSE: No absorption correction was done
;
# Added during the CSD deposition process: Friday 09 September 2016 11:01 AM
# end Validation Reply Form


_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
'4,7-dithien-2-yl-2,1,3-benzothiadiazole'
;
_chemical_name_common            DTBT
_chemical_formula_moiety         ?
_chemical_formula_structural     'C14 H7.6 N2 S3'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C14 H8 N2 S3'
_chemical_formula_weight         296.88
_chemical_melting_point          ?
_chemical_compound_source        ?

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pcab

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

_cell_length_a                   9.969(1)
_cell_length_b                   12.775(1)
_cell_length_c                   20.278(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2582.6(1)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16731
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      30.034

_exptl_crystal_description       fiber
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1204
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22691
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         30.08
_reflns_number_total             3766
_reflns_number_observed          2263
_reflns_observed_criterion       >2sigma(I)
_diffrn_reflns_theta_full        25.057
_diffrn_measured_fraction_theta_full 0.990


_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'Diamond V3.2K'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement on F² for ALL reflections except for 0 with very negative F² 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F², conventional R-factors R 
 are based on F, with F set to zero for negative F². The observed criterion 
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1018P)^2^+0.4725P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3766
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_obs          0.0511
_refine_ls_wR_factor_all         0.1767
_refine_ls_wR_factor_obs         0.1483
_refine_ls_goodness_of_fit_all   0.997
_refine_ls_goodness_of_fit_obs   1.091
_refine_ls_restrained_S_all      0.997
_refine_ls_restrained_S_obs      1.091
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.88477(7) 0.01353(5) 0.35971(4) 0.0737(3) Uani 1 d . .
S2 S 0.60144(7) 0.18262(5) 0.22775(3) 0.0555(3) Uani 0.866(3) d P .
S2C C 0.60144(7) 0.18262(5) 0.22775(3) 0.0555(3) Uani 0.13 d P .
S3 S 1.15430(11) 0.40155(10) 0.49319(5) 0.0897(5) Uani 0.716(3) d P .
S3C C 1.15430(11) 0.40155(10) 0.49319(5) 0.0897(5) Uani 0.28 d P .
N1 N 0.7936(2) 0.09486(14) 0.31902(10) 0.0575(5) Uani 1 d . .
N2 N 0.9740(2) 0.0914(2) 0.40381(11) 0.0644(6) Uani 1 d . .
C1 C 0.8310(2) 0.1908(2) 0.33892(10) 0.0458(5) Uani 1 d . .
C2 C 0.7756(2) 0.2867(2) 0.31456(10) 0.0449(5) Uani 1 d . .
C3 C 0.8270(2) 0.3758(2) 0.34276(12) 0.0586(6) Uani 1 d . .
C4 C 0.9285(3) 0.3734(2) 0.39123(13) 0.0614(6) Uani 1 d . .
C5 C 0.9861(2) 0.2835(2) 0.41560(11) 0.0525(5) Uani 1 d . .
C6 C 0.9344(2) 0.1892(2) 0.38814(11) 0.0498(5) Uani 1 d . .
C7 C 0.6725(2) 0.2915(2) 0.26345(10) 0.0446(5) Uani 1 d . .
C8 C 0.4994(3) 0.2558(2) 0.17915(12) 0.0628(6) Uani 1 d . .
C9 C 0.5174(3) 0.3578(2) 0.18809(13) 0.0654(7) Uani 1 d . .
C10 C 0.6166(2) 0.3832(2) 0.23612(11) 0.0792(6) Uani 0.866(3) d P .
C10S S 0.6166(2) 0.3832(2) 0.23612(11) 0.0792(6) Uani 0.13 d P .
C11 C 1.0913(2) 0.2858(2) 0.46638(12) 0.0613(7) Uani 1 d . .
C12 C 1.2589(3) 0.3459(4) 0.5443(2) 0.0988(12) Uani 1 d . .
C13 C 1.2551(3) 0.2423(4) 0.5459(2) 0.0925(10) Uani 1 d . .
C14 C 1.1535(2) 0.1878(2) 0.50095(7) 0.0829(6) Uani 0.716(3) d P .
C14S S 1.1535(2) 0.1878(2) 0.50095(7) 0.0829(6) Uani 0.28 d P .
H1 H 0.7850 0.4517 0.3190 0.100 Uiso 1 d . .
H2 H 0.9599 0.4385 0.4108 0.100 Uiso 1 d . .
H3 H 0.4438 0.2223 0.1526 0.100 Uiso 1 d . .
H4 H 1.3206 0.3902 0.5785 0.100 Uiso 1 d . .
H5 H 0.6554 0.4623 0.2460 0.100 Uiso 0.87 d P .
H6 H 1.3312 0.2090 0.5836 0.100 Uiso 1 d . .
H7 H 0.4758 0.4139 0.1654 0.100 Uiso 1 d . .
H8 H 1.1207 0.1122 0.4861 0.100 Uiso 0.72 d 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 N2 1.607(2) . ?
S1 N1 1.608(2) . ?
S2 C8 1.697(3) . ?
S2 C7 1.721(2) . ?
S2C C8 1.697(3) . ?
S2C C7 1.721(2) . ?
S3 C12 1.633(4) . ?
S3 C11 1.696(3) . ?
S3C C12 1.633(4) . ?
S3C C11 1.696(3) . ?
N1 C1 1.343(3) . ?
N2 C6 1.348(3) . ?
C1 C2 1.432(3) . ?
C1 C6 1.436(3) . ?
C2 C3 1.374(3) . ?
C2 C7 1.461(3) . ?
C3 C4 1.411(4) . ?
C3 H1 1.161(2) . ?
C4 C5 1.375(3) . ?
C4 H2 0.973(2) . ?
C5 C6 1.424(3) . ?
C5 C11 1.471(3) . ?
C7 C10S 1.411(3) . ?
C7 C10 1.411(3) . ?
C8 C9 1.328(4) . ?
C8 H3 0.883(3) . ?
C9 C10S 1.425(4) . ?
C9 C10 1.425(4) . ?
C9 H7 0.947(2) . ?
C10 H5 1.100(3) . ?
C10S H5 1.100(3) . ?
C11 C14S 1.563(3) . ?
C11 C14 1.563(3) . ?
C12 C13 1.325(6) . ?
C12 H4 1.086(3) . ?
C13 C14S 1.530(4) . ?
C13 C14 1.530(4) . ?
C13 H6 1.159(3) . ?
C14 H8 1.063(2) . ?
C14S H8 1.063(2) . ?

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
N2 S1 N1 101.43(11) . . ?
C8 S2 C7 92.61(12) . . ?
C8 S2C C7 92.61(12) . . ?
C12 S3 C11 93.4(2) . . ?
C12 S3C C11 93.4(2) . . ?
C1 N1 S1 106.2(2) . . ?
C6 N2 S1 106.3(2) . . ?
N1 C1 C2 124.8(2) . . ?
N1 C1 C6 113.3(2) . . ?
C2 C1 C6 121.9(2) . . ?
C3 C2 C1 114.9(2) . . ?
C3 C2 C7 121.5(2) . . ?
C1 C2 C7 123.5(2) . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H1 112.6(2) . . ?
C4 C3 H1 124.5(2) . . ?
C5 C4 C3 124.6(2) . . ?
C5 C4 H2 115.7(2) . . ?
C3 C4 H2 119.7(3) . . ?
C4 C5 C6 114.5(2) . . ?
C4 C5 C11 122.2(2) . . ?
C6 C5 C11 123.3(2) . . ?
N2 C6 C5 125.9(2) . . ?
N2 C6 C1 112.8(2) . . ?
C5 C6 C1 121.3(2) . . ?
C10S C7 C10 0.0(3) . . ?
C10S C7 C2 126.3(2) . . ?
C10 C7 C2 126.3(2) . . ?
C10S C7 S2 110.1(2) . . ?
C10 C7 S2 110.1(2) . . ?
C2 C7 S2 123.6(2) . . ?
C10S C7 S2C 110.1(2) . . ?
C10 C7 S2C 110.1(2) . . ?
C2 C7 S2C 123.6(2) . . ?
S2 C7 S2C 0.00(6) . . ?
C9 C8 S2 112.4(2) . . ?
C9 C8 S2C 112.4(2) . . ?
S2 C8 S2C 0.00(6) . . ?
C9 C8 H3 130.1(3) . . ?
S2 C8 H3 117.5(2) . . ?
S2C C8 H3 117.5(2) . . ?
C8 C9 C10S 114.2(2) . . ?
C8 C9 C10 114.2(2) . . ?
C10S C9 C10 0.0(3) . . ?
C8 C9 H7 128.1(3) . . ?
C10S C9 H7 117.6(3) . . ?
C10 C9 H7 117.6(3) . . ?
C7 C10 C9 110.7(2) . . ?
C7 C10 H5 123.5(2) . . ?
C9 C10 H5 125.3(2) . . ?
C7 C10S C9 110.7(2) . . ?
C7 C10S H5 123.5(2) . . ?
C9 C10S H5 125.3(2) . . ?
C5 C11 C14S 125.6(2) . . ?
C5 C11 C14 125.6(2) . . ?
C14S C11 C14 0.0(2) . . ?
C5 C11 S3C 120.4(2) . . ?
C14S C11 S3C 114.1(2) . . ?
C14 C11 S3C 114.1(2) . . ?
C5 C11 S3 120.4(2) . . ?
C14S C11 S3 114.1(2) . . ?
C14 C11 S3 114.1(2) . . ?
S3C C11 S3 0.00(9) . . ?
C13 C12 S3 115.6(3) . . ?
C13 C12 S3C 115.6(3) . . ?
S3 C12 S3C 0.00(10) . . ?
C13 C12 H4 121.4(4) . . ?
S3 C12 H4 122.7(4) . . ?
S3C C12 H4 122.7(4) . . ?
C12 C13 C14S 117.3(3) . . ?
C12 C13 C14 117.3(3) . . ?
C14S C13 C14 0.0(2) . . ?
C12 C13 H6 111.4(4) . . ?
C14S C13 H6 131.3(4) . . ?
C14 C13 H6 131.3(4) . . ?
C13 C14 C11 99.5(2) . . ?
C13 C14 H8 141.8(2) . . ?
C11 C14 H8 118.58(15) . . ?
C13 C14S C11 99.5(2) . . ?
C13 C14S H8 141.8(2) . . ?
C11 C14S H8 118.58(15) . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.058
_exptl_crystal_preparation       ', Luminescent'
