# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DTDCNBT

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 N4 S3'
_chemical_formula_sum            'C16 H6 N4 S3'
_chemical_formula_weight         350.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   7.1953(4)
_cell_length_b                   17.8923(9)
_cell_length_c                   11.5414(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.832(5)
_cell_angle_gamma                90
_cell_volume                     1442.76(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      3.0910
_cell_measurement_theta_max      28.0990

_exptl_crystal_description       blocks
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.516
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            5053
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2870
_reflns_number_gt                2360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.5798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0302(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     251
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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_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 0.78766(9) 0.74120(3) 0.72163(5) 0.03110(19) Uani 1 1 d . . . . .
N2 N 0.7856(3) 0.65738(10) 0.77267(16) 0.0263(4) Uani 1 1 d . . . . .
C3 C 0.7712(3) 0.61136(12) 0.67845(18) 0.0198(5) Uani 1 1 d . . . . .
C4 C 0.7654(3) 0.53143(12) 0.68458(18) 0.0182(4) Uani 1 1 d D . . . .
C5 C 0.7519(3) 0.49548(12) 0.57612(18) 0.0185(4) Uani 1 1 d . . . . .
C6 C 0.7512(3) 0.53464(12) 0.46627(18) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.7530(3) 0.61216(12) 0.45769(18) 0.0188(5) Uani 1 1 d D . . . .
C8 C 0.7638(3) 0.65015(12) 0.56895(19) 0.0201(5) Uani 1 1 d . . . . .
N9 N 0.7712(3) 0.72491(10) 0.58249(17) 0.0275(4) Uani 1 1 d . . . . .
C10 C 0.7836(9) 0.4909(3) 0.7965(3) 0.0180(8) Uani 0.877(3) 1 d D U P A 1
S11 S 0.6853(3) 0.52566(8) 0.90994(10) 0.0271(3) Uani 0.877(3) 1 d D U P A 1
C12 C 0.7681(5) 0.45067(19) 0.9991(3) 0.0281(7) Uani 0.877(3) 1 d D U P A 1
H12A H 0.7459 0.4437 1.0763 0.034 Uiso 0.877(3) 1 calc R U P A 1
C13 C 0.8692(5) 0.40207(19) 0.9474(3) 0.0276(7) Uani 0.877(3) 1 d D U P A 1
H13A H 0.9276 0.3579 0.9851 0.033 Uiso 0.877(3) 1 calc R U P A 1
C14 C 0.8774(16) 0.4244(6) 0.8327(10) 0.037(2) Uani 0.877(3) 1 d D U P A 1
H14A H 0.9415 0.3964 0.7841 0.044 Uiso 0.877(3) 1 calc R U P A 1
C10' C 0.758(8) 0.501(2) 0.800(3) 0.017(5) Uiso 0.123(3) 1 d D U P A 2
S11' S 0.882(3) 0.4172(11) 0.8317(17) 0.023(3) Uiso 0.123(3) 1 d D U P A 2
C12' C 0.840(5) 0.4164(15) 0.971(2) 0.027(4) Uiso 0.123(3) 1 d D U P A 2
H12B H 0.8807 0.3778 1.0276 0.032 Uiso 0.123(3) 1 calc R U P A 2
C13' C 0.740(4) 0.4776(12) 0.990(2) 0.024(5) Uiso 0.123(3) 1 d D U P A 2
H13B H 0.7054 0.4864 1.0631 0.029 Uiso 0.123(3) 1 calc R U P A 2
C14' C 0.694(8) 0.526(2) 0.894(3) 0.031(6) Uiso 0.123(3) 1 d D U P A 2
H14B H 0.6252 0.5718 0.8946 0.037 Uiso 0.123(3) 1 calc R U P A 2
C15 C 0.7317(3) 0.41517(12) 0.56668(18) 0.0203(5) Uani 1 1 d . . . . .
N15 N 0.7105(3) 0.35203(11) 0.55241(17) 0.0308(5) Uani 1 1 d . . . . .
C16 C 0.7537(3) 0.48669(12) 0.36580(18) 0.0217(5) Uani 1 1 d . . . . .
N16 N 0.7599(3) 0.44430(11) 0.29239(17) 0.0323(5) Uani 1 1 d . . . . .
C17 C 0.7447(17) 0.6525(4) 0.3459(3) 0.0207(12) Uani 0.859(3) 1 d D U P B 1
S18 S 0.82875(15) 0.74346(5) 0.34524(8) 0.0318(3) Uani 0.859(3) 1 d D U P B 1
C19 C 0.7729(7) 0.7454(2) 0.1922(3) 0.0316(9) Uani 0.859(3) 1 d D U P B 1
H19A H 0.8004 0.7864 0.1467 0.038 Uiso 0.859(3) 1 calc R U P B 1
C20 C 0.6849(9) 0.6818(3) 0.1433(4) 0.0298(9) Uani 0.859(3) 1 d D U P B 1
H20A H 0.6405 0.6733 0.0600 0.036 Uiso 0.859(3) 1 calc R U P B 1
C21 C 0.6681(9) 0.6303(3) 0.2313(5) 0.0302(12) Uani 0.859(3) 1 d D U P B 1
H21A H 0.6076 0.5831 0.2127 0.036 Uiso 0.859(3) 1 calc R U P B 1
C17' C 0.732(11) 0.656(2) 0.3499(16) 0.024(5) Uiso 0.141(3) 1 d D U P B 2
S18' S 0.6476(14) 0.6175(5) 0.2090(9) 0.026(2) Uiso 0.141(3) 1 d D U P B 2
C19' C 0.714(7) 0.6958(16) 0.144(2) 0.031(5) Uiso 0.141(3) 1 d D U P B 2
H19B H 0.6919 0.7024 0.0602 0.037 Uiso 0.141(3) 1 calc R U P B 2
C20' C 0.800(4) 0.7473(15) 0.225(2) 0.030(5) Uiso 0.141(3) 1 d D U P B 2
H20B H 0.8314 0.7965 0.2049 0.036 Uiso 0.141(3) 1 calc R U P B 2
C21' C 0.837(4) 0.7186(13) 0.340(2) 0.038(5) Uiso 0.141(3) 1 d D U P B 2
H21B H 0.9262 0.7404 0.4060 0.046 Uiso 0.141(3) 1 calc R U P B 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 N9 1.6084(19) . ?
S1 N2 1.6127(19) . ?
N2 C3 1.348(3) . ?
C3 C8 1.432(3) . ?
C3 C4 1.433(3) . ?
C4 C5 1.390(3) . ?
C4 C10' 1.446(15) . ?
C4 C10 1.460(3) . ?
C5 C15 1.446(3) . ?
C5 C6 1.448(3) . ?
C6 C7 1.391(3) . ?
C6 C16 1.446(3) . ?
C7 C8 1.438(3) . ?
C7 C17' 1.451(17) . ?
C7 C17 1.466(3) . ?
C8 N9 1.346(3) . ?
C10 C14 1.382(10) . ?
C10 S11 1.744(3) . ?
S11 C12 1.709(4) . ?
C12 C13 1.359(4) . ?
C13 C14 1.397(11) . ?
C10' C14' 1.36(2) . ?
C10' S11' 1.744(19) . ?
S11' C12' 1.703(18) . ?
C12' C13' 1.355(17) . ?
C13' C14' 1.38(2) . ?
C15 N15 1.146(3) . ?
C16 N16 1.146(3) . ?
C17 C21 1.365(7) . ?
C17 S18 1.738(5) . ?
S18 C19 1.716(4) . ?
C19 C20 1.359(5) . ?
C20 C21 1.398(6) . ?
C17' C21' 1.37(2) . ?
C17' S18' 1.74(2) . ?
S18' C19' 1.709(18) . ?
C19' C20' 1.350(17) . ?
C20' C21' 1.397(18) . ?

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
N9 S1 N2 101.02(10) . . ?
C3 N2 S1 106.21(15) . . ?
N2 C3 C8 113.29(19) . . ?
N2 C3 C4 124.56(19) . . ?
C8 C3 C4 122.15(19) . . ?
C5 C4 C3 114.45(18) . . ?
C5 C4 C10' 130.1(17) . . ?
C3 C4 C10' 115.2(16) . . ?
C5 C4 C10 122.6(3) . . ?
C3 C4 C10 122.8(3) . . ?
C4 C5 C15 120.79(19) . . ?
C4 C5 C6 123.35(19) . . ?
C15 C5 C6 115.84(18) . . ?
C7 C6 C16 122.18(18) . . ?
C7 C6 C5 123.16(18) . . ?
C16 C6 C5 114.64(18) . . ?
C6 C7 C8 114.03(18) . . ?
C6 C7 C17' 127.1(17) . . ?
C8 C7 C17' 118.8(19) . . ?
C6 C7 C17 123.6(3) . . ?
C8 C7 C17 122.3(3) . . ?
N9 C8 C3 112.77(19) . . ?
N9 C8 C7 124.44(19) . . ?
C3 C8 C7 122.78(19) . . ?
C8 N9 S1 106.71(15) . . ?
C14 C10 C4 129.0(5) . . ?
C14 C10 S11 109.7(5) . . ?
C4 C10 S11 121.4(3) . . ?
C12 S11 C10 91.51(16) . . ?
C13 C12 S11 112.6(2) . . ?
C12 C13 C14 112.4(5) . . ?
C10 C14 C13 113.8(8) . . ?
C14' C10' C4 135(2) . . ?
C14' C10' S11' 111.7(14) . . ?
C4 C10' S11' 112.7(16) . . ?
C12' S11' C10' 90.5(11) . . ?
C13' C12' S11' 111.5(16) . . ?
C12' C13' C14' 114.6(19) . . ?
C10' C14' C13' 112(2) . . ?
N15 C15 C5 176.0(2) . . ?
N16 C16 C6 174.7(2) . . ?
C21 C17 C7 129.2(4) . . ?
C21 C17 S18 109.2(3) . . ?
C7 C17 S18 121.6(3) . . ?
C19 S18 C17 91.60(18) . . ?
C20 C19 S18 112.4(3) . . ?
C19 C20 C21 111.3(4) . . ?
C17 C21 C20 115.3(4) . . ?
C21' C17' C7 125(3) . . ?
C21' C17' S18' 109.2(16) . . ?
C7 C17' S18' 122(2) . . ?
C19' S18' C17' 90.6(11) . . ?
C20' C19' S18' 112.8(18) . . ?
C19' C20' C21' 111(2) . . ?
C17' C21' C20' 113.1(18) . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

#===END

_database_code_depnum_ccdc_archive 'CCDC 1020253'
