# 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_5

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 N4 S3'
_chemical_formula_sum            'C12 H4 N4 S3'
_chemical_formula_weight         300.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.22656(17)
_cell_length_b                   18.9016(4)
_cell_length_c                   8.35979(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1141.89(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    1641
_cell_measurement_theta_min      4.6760
_cell_measurement_theta_max      73.0770

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    5.844
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.355
_exptl_absorpt_correction_T_max  0.672
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            2149
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.679
_diffrn_reflns_theta_max         73.366
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.633
_diffrn_reflns_point_group_measured_fraction_full 0.657
_reflns_number_total             1453
_reflns_number_gt                1404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.217
_reflns_Friedel_fraction_max     0.243
_reflns_Friedel_fraction_full    0.268

_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,
_computing_cell_refinement       CrysAlisPro,
_computing_data_reduction        CrysAlisPro,
_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)+(0.0403P)²] 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       0.0036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).

 Results of chirality/polarity tests
  _refine_ls_R_factor_obs+         0.0249
  _refine_ls_wR_factor_obs+        0.0629
  _refine_ls_abs_structure_Flack+  0.05(2)
  _refine_ls_R_factor_obs-         0.0367
  _refine_ls_wR_factor_obs-        0.0996
  _refine_ls_abs_structure_Flack-  0.94(2)
;
_refine_ls_abs_structure_Flack   0.05(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1453
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_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 0.65690(11) 0.00296(3) 0.20501(11) 0.02693(19) Uani 1 1 d . . . . .
N2 N 0.5939(3) 0.02664(12) 0.3818(4) 0.0255(5) Uani 1 1 d . . . . .
C3 C 0.5970(4) 0.09830(14) 0.3807(4) 0.0200(5) Uani 1 1 d . . . . .
N4 N 0.5460(3) 0.13840(13) 0.5062(3) 0.0211(5) Uani 1 1 d . . . . .
C5 C 0.5580(4) 0.20779(15) 0.4795(4) 0.0183(6) Uani 1 1 d . . . . .
C6 C 0.5035(4) 0.25569(16) 0.6065(4) 0.0201(6) Uani 1 1 d . . . . .
C7 C 0.4395(4) 0.23720(16) 0.7628(4) 0.0245(6) Uani 1 1 d . . . . .
H7A H 0.4262 0.1899 0.7992 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4000(4) 0.29483(18) 0.8531(4) 0.0289(7) Uani 1 1 d . . . . .
H8A H 0.3546 0.2925 0.9596 0.035 Uiso 1 1 calc R U . . .
S9 S 0.44194(10) 0.37299(4) 0.75198(10) 0.0287(2) Uani 1 1 d . . . . .
C10 C 0.5134(4) 0.32816(16) 0.5836(4) 0.0218(6) Uani 1 1 d . . . . .
C11 C 0.5752(4) 0.35694(15) 0.4364(4) 0.0206(6) Uani 1 1 d . . . . .
S12 S 0.59503(10) 0.44495(3) 0.38486(10) 0.02557(18) Uani 1 1 d . . . . .
C13 C 0.6781(4) 0.42337(15) 0.1963(4) 0.0270(6) Uani 1 1 d . . . . .
H13A H 0.7117 0.4574 0.1179 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6899(4) 0.35239(16) 0.1732(4) 0.0231(6) Uani 1 1 d . . . . .
H14A H 0.7327 0.3311 0.0771 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6303(4) 0.31359(16) 0.3104(4) 0.0208(6) Uani 1 1 d . . . . .
C16 C 0.6218(4) 0.23731(14) 0.3277(4) 0.0185(5) Uani 1 1 d . . . . .
N17 N 0.6713(3) 0.19739(11) 0.2044(3) 0.0203(5) Uani 1 1 d . . . . .
C18 C 0.6567(4) 0.12693(14) 0.2313(4) 0.0198(6) Uani 1 1 d . . . . .
N19 N 0.6956(4) 0.07816(13) 0.1198(3) 0.0261(6) 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 0.0336(4) 0.0220(3) 0.0252(3) -0.0038(3) 0.0008(3) -0.0008(2)
N2 0.0258(11) 0.0252(12) 0.0254(12) -0.0015(12) -0.0012(12) -0.0009(9)
C3 0.0167(11) 0.0234(12) 0.0200(13) -0.0002(13) 0.0008(12) -0.0016(9)
N4 0.0201(11) 0.0248(11) 0.0183(11) 0.0006(10) -0.0002(10) -0.0002(9)
C5 0.0149(12) 0.0224(12) 0.0175(14) 0.0002(11) 0.0006(9) -0.0001(10)
C6 0.0184(13) 0.0262(14) 0.0156(13) -0.0015(11) 0.0010(11) 0.0003(11)
C7 0.0238(14) 0.0312(14) 0.0184(13) -0.0035(14) 0.0043(13) -0.0046(10)
C8 0.0298(15) 0.0383(16) 0.0186(15) -0.0051(13) 0.0033(12) -0.0028(12)
S9 0.0334(4) 0.0304(4) 0.0223(4) -0.0085(3) 0.0034(3) -0.0002(3)
C10 0.0188(12) 0.0297(14) 0.0170(13) -0.0061(12) 0.0017(11) -0.0002(10)
C11 0.0184(13) 0.0237(13) 0.0196(14) 0.0012(12) -0.0021(11) -0.0001(10)
S12 0.0298(3) 0.0208(3) 0.0261(3) -0.0007(3) -0.0034(3) 0.0005(2)
C13 0.0291(15) 0.0254(13) 0.0264(15) 0.0050(14) -0.0006(14) -0.0014(10)
C14 0.0209(13) 0.0273(13) 0.0212(15) 0.0015(12) -0.0018(11) 0.0008(10)
C15 0.0167(12) 0.0276(15) 0.0181(13) 0.0009(12) -0.0016(11) 0.0009(11)
C16 0.0151(12) 0.0231(13) 0.0172(12) 0.0005(11) -0.0011(11) 0.0005(10)
N17 0.0203(11) 0.0232(11) 0.0173(11) -0.0006(11) 0.0007(10) -0.0008(8)
C18 0.0182(12) 0.0226(13) 0.0187(15) -0.0008(12) 0.0009(11) -0.0013(9)
N19 0.0312(13) 0.0255(11) 0.0215(13) -0.0034(10) 0.0003(10) 0.0003(10)

_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 1.610(3) . ?
S1 N19 1.614(3) . ?
N2 C3 1.355(4) . ?
C3 N4 1.346(4) . ?
C3 C18 1.428(4) . ?
N4 C5 1.333(4) . ?
C5 C6 1.450(4) . ?
C5 C16 1.461(4) . ?
C6 C10 1.385(4) . ?
C6 C7 1.429(4) . ?
C7 C8 1.356(5) . ?
C8 S9 1.729(3) . ?
S9 C10 1.722(3) . ?
C10 C11 1.418(4) . ?
C11 C15 1.392(4) . ?
C11 S12 1.724(3) . ?
S12 C13 1.736(4) . ?
C13 C14 1.358(4) . ?
C14 C15 1.428(4) . ?
C15 C16 1.450(4) . ?
C16 N17 1.326(4) . ?
N17 C18 1.355(3) . ?
C18 N19 1.341(4) . ?

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 N19 102.07(14) . . ?
C3 N2 S1 105.5(2) . . ?
N4 C3 N2 123.6(3) . . ?
N4 C3 C18 123.5(2) . . ?
N2 C3 C18 112.9(3) . . ?
C5 N4 C3 113.9(3) . . ?
N4 C5 C6 118.3(3) . . ?
N4 C5 C16 122.8(3) . . ?
C6 C5 C16 118.9(2) . . ?
C10 C6 C7 112.6(3) . . ?
C10 C6 C5 120.1(3) . . ?
C7 C6 C5 127.2(3) . . ?
C8 C7 C6 112.4(3) . . ?
C7 C8 S9 112.1(3) . . ?
C10 S9 C8 91.83(15) . . ?
C6 C10 C11 121.1(3) . . ?
C6 C10 S9 111.0(2) . . ?
C11 C10 S9 128.0(2) . . ?
C15 C11 C10 121.4(3) . . ?
C15 C11 S12 110.8(2) . . ?
C10 C11 S12 127.8(2) . . ?
C11 S12 C13 91.65(14) . . ?
C14 C13 S12 112.5(2) . . ?
C13 C14 C15 112.0(3) . . ?
C11 C15 C14 113.1(3) . . ?
C11 C15 C16 119.8(3) . . ?
C14 C15 C16 127.1(3) . . ?
N17 C16 C15 118.5(3) . . ?
N17 C16 C5 122.9(2) . . ?
C15 C16 C5 118.7(3) . . ?
C16 N17 C18 114.2(3) . . ?
N19 C18 N17 123.0(3) . . ?
N19 C18 C3 114.3(2) . . ?
N17 C18 C3 122.8(3) . . ?
C18 N19 S1 105.2(2) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-4

#===END


_database_code_depnum_ccdc_archive 'CCDC 992593'
