# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013

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#
#                 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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N4 S'
_chemical_formula_sum            'C26 H17 N4 S'
_chemical_formula_weight         417.50

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3437(17)
_cell_length_b                   10.538(2)
_cell_length_c                   11.5632(15)
_cell_angle_alpha                105.416(15)
_cell_angle_beta                 94.821(13)
_cell_angle_gamma                114.063(19)
_cell_volume                     978.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.05(10)
_cell_measurement_reflns_used    2268
_cell_measurement_theta_min      4.0607
_cell_measurement_theta_max      72.4351


_exptl_crystal_description       Rods
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             434
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5933
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         67.00
_reflns_number_total             3463
_reflns_number_gt                2746
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1125P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3463
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0573(3) 0.6667(3) 0.0489(2) 0.0268(5) Uani 1 1 d . . .
C2 C -0.0140(3) 0.5544(3) 0.1844(2) 0.0272(5) Uani 1 1 d . . .
C3 C 0.1531(3) 0.6541(3) 0.2153(2) 0.0288(5) Uani 1 1 d . . .
C4 C 0.2614(3) 0.6498(3) 0.3031(2) 0.0298(5) Uani 1 1 d . . .
H4 H 0.3701 0.7150 0.3229 0.036 Uiso 1 1 calc R . .
C5 C -0.0706(3) 0.4489(3) 0.2426(2) 0.0275(5) Uani 1 1 d . . .
H5 H -0.1789 0.3823 0.2226 0.033 Uiso 1 1 calc R . .
C6 C 0.2003(3) 0.5444(3) 0.3595(2) 0.0295(5) Uani 1 1 d . . .
C7 C 0.0368(3) 0.4441(3) 0.3313(2) 0.0281(5) Uani 1 1 d . . .
C8 C 0.1222(3) 0.3653(3) 0.4692(2) 0.0293(5) Uani 1 1 d . . .
C9 C 0.1182(3) 0.2771(3) 0.5491(2) 0.0285(5) Uani 1 1 d . . .
C10 C 0.2599(3) 0.2957(3) 0.6184(2) 0.0340(6) Uani 1 1 d . . .
H10 H 0.3590 0.3632 0.6128 0.041 Uiso 1 1 calc R . .
C11 C 0.2522(3) 0.2134(3) 0.6955(2) 0.0368(6) Uani 1 1 d . . .
H11 H 0.3467 0.2267 0.7418 0.044 Uiso 1 1 calc R . .
C12 C 0.1064(3) 0.1120(3) 0.7045(2) 0.0337(6) Uani 1 1 d . . .
H12 H 0.1024 0.0583 0.7573 0.040 Uiso 1 1 calc R . .
C13 C -0.0345(3) 0.0908(3) 0.6337(2) 0.0314(6) Uani 1 1 d . . .
H13 H -0.1331 0.0215 0.6383 0.038 Uiso 1 1 calc R . .
C14 C -0.0288(3) 0.1723(3) 0.5566(2) 0.0306(6) Uani 1 1 d . . .
H14 H -0.1237 0.1572 0.5095 0.037 Uiso 1 1 calc R . .
C15 C -0.1681(3) 0.6836(3) -0.0392(2) 0.0274(5) Uani 1 1 d . . .
C16 C -0.1121(3) 0.7939(3) -0.0931(2) 0.0340(6) Uani 1 1 d . . .
H16 H -0.0031 0.8581 -0.0745 0.041 Uiso 1 1 calc R . .
C17 C -0.2181(3) 0.8080(3) -0.1739(3) 0.0387(6) Uani 1 1 d . . .
H17 H -0.1800 0.8808 -0.2101 0.046 Uiso 1 1 calc R . .
C18 C -0.3810(3) 0.7139(3) -0.2012(2) 0.0367(6) Uani 1 1 d . . .
H18 H -0.4520 0.7238 -0.2554 0.044 Uiso 1 1 calc R . .
C19 C -0.4380(3) 0.6049(3) -0.1475(2) 0.0339(6) Uani 1 1 d . . .
H19 H -0.5473 0.5420 -0.1653 0.041 Uiso 1 1 calc R . .
C20 C -0.3317(3) 0.5898(3) -0.0672(2) 0.0312(6) Uani 1 1 d . . .
H20 H -0.3703 0.5163 -0.0318 0.037 Uiso 1 1 calc R . .
C21 C 0.3658(3) 0.8577(3) 0.1701(2) 0.0294(5) Uani 1 1 d . . .
C22 C 0.4433(3) 0.9754(3) 0.2788(3) 0.0358(6) Uani 1 1 d . . .
H22 H 0.3907 0.9868 0.3428 0.043 Uiso 1 1 calc R . .
C23 C 0.6018(3) 1.0765(3) 0.2903(3) 0.0382(6) Uani 1 1 d . . .
H23 H 0.6555 1.1567 0.3619 0.046 Uiso 1 1 calc R . .
C24 C 0.6789(3) 1.0566(3) 0.1944(3) 0.0373(6) Uani 1 1 d . . .
H24 H 0.7844 1.1240 0.2021 0.045 Uiso 1 1 calc R . .
C25 C 0.6006(3) 0.9380(3) 0.0881(3) 0.0374(6) Uani 1 1 d . . .
H25 H 0.6538 0.9255 0.0247 0.045 Uiso 1 1 calc R . .
C26 C 0.4421(3) 0.8368(3) 0.0746(2) 0.0332(6) Uani 1 1 d . . .
H26 H 0.3888 0.7567 0.0028 0.040 Uiso 1 1 calc R . .
N1 N 0.2004(2) 0.7550(2) 0.15373(19) 0.0287(5) Uani 1 1 d . . .
N2 N 0.0983(2) 0.7651(2) 0.07031(19) 0.0285(5) Uani 1 1 d . . .
N3 N -0.1188(2) 0.5610(2) 0.09817(19) 0.0286(5) Uani 1 1 d . . .
N4 N -0.0040(3) 0.3444(2) 0.39508(18) 0.0300(5) Uani 1 1 d . . .
S1 S 0.30350(7) 0.51148(7) 0.47102(6) 0.0319(2) 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
C1 0.0251(13) 0.0265(12) 0.0315(13) 0.0092(10) 0.0076(10) 0.0140(10)
C2 0.0284(13) 0.0252(12) 0.0310(13) 0.0081(9) 0.0065(10) 0.0156(11)
C3 0.0320(14) 0.0277(12) 0.0314(13) 0.0100(10) 0.0092(10) 0.0172(11)
C4 0.0281(13) 0.0287(12) 0.0344(13) 0.0106(10) 0.0049(10) 0.0147(11)
C5 0.0267(12) 0.0260(12) 0.0298(12) 0.0077(9) 0.0034(10) 0.0132(10)
C6 0.0308(13) 0.0313(12) 0.0314(13) 0.0100(10) 0.0052(10) 0.0193(11)
C7 0.0304(13) 0.0261(12) 0.0309(13) 0.0086(10) 0.0078(10) 0.0159(11)
C8 0.0289(13) 0.0284(12) 0.0329(13) 0.0091(10) 0.0067(10) 0.0156(11)
C9 0.0325(13) 0.0271(12) 0.0299(13) 0.0090(10) 0.0068(10) 0.0174(11)
C10 0.0315(14) 0.0364(14) 0.0354(14) 0.0131(11) 0.0045(11) 0.0161(12)
C11 0.0368(15) 0.0417(15) 0.0382(15) 0.0171(12) 0.0030(11) 0.0220(13)
C12 0.0405(15) 0.0358(14) 0.0361(14) 0.0173(11) 0.0103(11) 0.0238(12)
C13 0.0328(14) 0.0321(13) 0.0351(14) 0.0126(10) 0.0119(11) 0.0182(11)
C14 0.0334(14) 0.0336(13) 0.0327(13) 0.0108(10) 0.0081(10) 0.0223(11)
C15 0.0269(13) 0.0294(12) 0.0298(12) 0.0095(10) 0.0055(10) 0.0164(11)
C16 0.0310(14) 0.0373(14) 0.0389(14) 0.0175(11) 0.0091(11) 0.0169(12)
C17 0.0391(15) 0.0429(15) 0.0449(16) 0.0264(13) 0.0096(12) 0.0212(13)
C18 0.0369(15) 0.0433(15) 0.0349(14) 0.0162(12) 0.0001(11) 0.0219(13)
C19 0.0284(13) 0.0326(13) 0.0409(15) 0.0116(11) 0.0038(11) 0.0149(11)
C20 0.0351(14) 0.0295(12) 0.0349(13) 0.0144(10) 0.0090(11) 0.0174(11)
C21 0.0254(13) 0.0279(12) 0.0405(14) 0.0171(10) 0.0040(10) 0.0141(11)
C22 0.0294(14) 0.0348(14) 0.0469(16) 0.0136(12) 0.0064(11) 0.0182(12)
C23 0.0293(14) 0.0287(13) 0.0544(17) 0.0088(11) 0.0003(12) 0.0155(11)
C24 0.0303(14) 0.0323(13) 0.0574(17) 0.0242(12) 0.0076(12) 0.0163(12)
C25 0.0344(15) 0.0416(15) 0.0443(16) 0.0226(12) 0.0114(12) 0.0189(13)
C26 0.0322(14) 0.0335(13) 0.0373(14) 0.0172(11) 0.0055(11) 0.0149(11)
N1 0.0247(11) 0.0299(11) 0.0355(11) 0.0142(9) 0.0051(8) 0.0142(9)
N2 0.0273(11) 0.0303(11) 0.0328(11) 0.0131(9) 0.0047(8) 0.0162(9)
N3 0.0287(11) 0.0279(10) 0.0329(11) 0.0108(8) 0.0048(8) 0.0161(9)
N4 0.0337(12) 0.0307(11) 0.0319(11) 0.0123(9) 0.0067(9) 0.0191(10)
S1 0.0305(4) 0.0339(4) 0.0364(4) 0.0164(3) 0.0048(3) 0.0168(3)

_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
C1 N3 1.329(3) . ?
C1 N2 1.350(3) . ?
C1 C15 1.487(3) . ?
C2 N3 1.373(3) . ?
C2 C5 1.396(3) . ?
C2 C3 1.428(4) . ?
C3 N1 1.380(3) . ?
C3 C4 1.394(4) . ?
C4 C6 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(4) . ?
C6 S1 1.736(3) . ?
C7 N4 1.388(3) . ?
C8 N4 1.300(3) . ?
C8 C9 1.468(3) . ?
C8 S1 1.758(3) . ?
C9 C14 1.396(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.390(4) . ?
C15 C16 1.399(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.381(4) . ?
C21 C22 1.389(4) . ?
C21 N1 1.440(3) . ?
C22 C23 1.397(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 N2 1.355(3) . ?

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
N3 C1 N2 127.3(2) . . ?
N3 C1 C15 118.4(2) . . ?
N2 C1 C15 114.3(2) . . ?
N3 C2 C5 119.9(2) . . ?
N3 C2 C3 120.8(2) . . ?
C5 C2 C3 119.3(2) . . ?
N1 C3 C4 122.3(2) . . ?
N1 C3 C2 116.0(2) . . ?
C4 C3 C2 121.7(2) . . ?
C6 C4 C3 117.3(2) . . ?
C6 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C2 C5 C7 119.5(2) . . ?
C2 C5 H5 120.3 . . ?
C7 C5 H5 120.3 . . ?
C4 C6 C7 122.7(2) . . ?
C4 C6 S1 128.1(2) . . ?
C7 C6 S1 109.21(18) . . ?
N4 C7 C5 125.1(2) . . ?
N4 C7 C6 115.3(2) . . ?
C5 C7 C6 119.6(2) . . ?
N4 C8 C9 123.8(2) . . ?
N4 C8 S1 115.58(19) . . ?
C9 C8 S1 120.61(19) . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 C8 119.9(2) . . ?
C10 C9 C8 121.2(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C20 C15 C16 118.9(2) . . ?
C20 C15 C1 119.6(2) . . ?
C16 C15 C1 121.5(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.7(2) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C26 C21 C22 121.8(2) . . ?
C26 C21 N1 118.2(2) . . ?
C22 C21 N1 120.0(2) . . ?
C21 C22 C23 118.7(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 118.7(3) . . ?
C21 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
N2 N1 C3 124.0(2) . . ?
N2 N1 C21 113.39(19) . . ?
C3 N1 C21 122.6(2) . . ?
C1 N2 N1 115.2(2) . . ?
C1 N3 C2 116.7(2) . . ?
C8 N4 C7 110.8(2) . . ?
C6 S1 C8 89.07(12) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 953369'