# 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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#  This CIF contains data from an original supplementary publication 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 919466'
_chemical_name_systematic        
;
3-Thiophen-2-yl-1,2,4-triazine
;
_chemical_formula_sum            'C7 H5 N3 S'
_chemical_formula_weight         163.20
_chemical_melting_point          345
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_preparation       acetone
_cell_length_a                   5.5650(5)
_cell_length_b                   13.2920(16)
_cell_length_c                   10.0843(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.248(9)
_cell_angle_gamma                90.00
_cell_volume                     741.50(14)
_symmetry_space_group_name_H-M   'P 1 21/n 1'
loop_
_symmetry_equiv_pos_as_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_formula_units_Z            4
_exptl_crystal_density_diffrn    1.462
_diffrn_ambient_temperature      293(2)
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_obs          0.0921
_refine_ls_wR_factor_ref         0.2595
_refine_ls_wR_factor_obs         0.2418
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
N1 N 0.0076(8) 1.0170(3) 0.7301(4) 0.0749(13) Uani 1 1 d . . .
N2 N 0.0522(7) 0.9260(3) 0.7840(4) 0.0662(11) Uani 1 1 d . . .
N4 N -0.2775(7) 0.9417(3) 0.9140(4) 0.0628(11) Uani 1 1 d . . .
C3 C -0.0880(7) 0.8922(3) 0.8736(4) 0.0524(10) Uani 1 1 d . C .
C5 C -0.3196(9) 1.0306(4) 0.8574(5) 0.0699(13) Uani 1 1 d . . .
H5 H -0.4494 1.0687 0.8798 0.105 Uiso 1 1 calc R . .
C6 C -0.1758(9) 1.0684(4) 0.7658(5) 0.0710(14) Uani 1 1 d . . .
H6 H -0.2097 1.1316 0.7288 0.106 Uiso 1 1 calc R . .
C7 C -0.0312(7) 0.7940(3) 0.9319(4) 0.0531(11) Uani 1 1 d . . .
C9 C 0.1543(10) 0.6365(5) 0.9929(5) 0.0789(15) Uani 1 1 d . . .
H9 H 0.2538 0.5801 1.0026 0.118 Uiso 1 1 calc R A 1
C10 C -0.0326(10) 0.6484(4) 1.0647(5) 0.0766(15) Uani 1 1 d . C .
H10 H -0.0684 0.6004 1.1267 0.115 Uiso 1 1 calc R B 1
S8A S 0.1977(3) 0.72558(16) 0.8880(2) 0.0755(9) Uani 0.603(4) 1 d P C 1
C11A C -0.1862(4) 0.74466(18) 1.0410(2) 0.0713(10) Uani 0.603(4) 1 d P C 1
H11A H -0.3231 0.7668 1.0776 0.107 Uiso 0.603(4) 1 calc PR C 1
S8B S -0.1862(4) 0.74466(18) 1.0410(2) 0.0713(10) Uani 0.397(4) 1 d P C 2
C11B C 0.1977(3) 0.72558(16) 0.8880(2) 0.0755(9) Uani 0.397(4) 1 d P C 2
H11B H 0.3087 0.7349 0.8265 0.113 Uiso 0.397(4) 1 calc PR C 2
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
N1 0.086(3) 0.070(3) 0.069(2) 0.015(2) 0.009(2) -0.008(2)
N2 0.064(2) 0.071(3) 0.065(2) 0.005(2) 0.0108(18) -0.0016(18)
N4 0.067(2) 0.055(2) 0.068(2) 0.0023(18) 0.0121(18) 0.0041(18)
C3 0.051(2) 0.054(2) 0.052(2) -0.0055(19) 0.0057(17) -0.0049(19)
C5 0.076(3) 0.055(3) 0.077(3) -0.001(2) 0.001(2) 0.007(2)
C6 0.079(3) 0.062(3) 0.070(3) 0.010(2) -0.003(2) -0.006(3)
C7 0.057(2) 0.051(2) 0.049(2) -0.0040(17) -0.0036(17) -0.0026(18)
C9 0.080(3) 0.082(4) 0.074(3) 0.009(3) 0.006(3) 0.027(3)
C10 0.086(3) 0.073(3) 0.070(3) 0.007(3) 0.006(3) 0.004(3)
S8A 0.0679(12) 0.0733(13) 0.0853(14) 0.0105(10) 0.0082(9) 0.0129(8)
C11A 0.0801(16) 0.0632(15) 0.0681(14) 0.0005(11) -0.0033(11) 0.0011(11)
S8B 0.0801(16) 0.0632(15) 0.0681(14) 0.0005(11) -0.0033(11) 0.0011(11)
C11B 0.0679(12) 0.0733(13) 0.0853(14) 0.0105(10) 0.0082(9) 0.0129(8)
_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
N1 C6 1.310(7) . ?
N1 N2 1.339(6) . ?
N2 C3 1.334(6) . ?
N4 C5 1.322(6) . ?
N4 C3 1.344(6) . ?
C3 C7 1.452(6) . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11A 1.610(5) . ?
C7 S8A 1.664(4) . ?
C9 C10 1.340(7) . ?
C9 S8A 1.623(6) . ?
C9 H9 0.9300 . ?
C10 C11A 1.542(6) . ?
C10 H10 0.9300 . ?
C11A H11A 0.9300 . ?
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
C6 N1 N2 118.4(4) . . ?
C3 N2 N1 118.8(4) . . ?
C5 N4 C3 114.5(4) . . ?
N2 C3 N4 125.2(4) . . ?
N2 C3 C7 117.3(4) . . ?
N4 C3 C7 117.4(4) . . ?
N4 C5 C6 121.7(5) . . ?
N4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
N1 C6 C5 121.3(5) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C3 C7 C11A 122.3(3) . . ?
C3 C7 S8A 121.5(3) . . ?
C11A C7 S8A 116.2(3) . . ?
C10 C9 S8A 116.4(4) . . ?
C10 C9 H9 121.8 . . ?
S8A C9 H9 121.8 . . ?
C9 C10 C11A 117.7(5) . . ?
C9 C10 H10 121.2 . . ?
C11A C10 H10 121.2 . . ?
C9 S8A C7 93.0(3) . . ?
C10 C11A C7 96.6(3) . . ?
C10 C11A H11A 131.7 . . ?
C7 C11A H11A 131.7 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C3 -1.4(7) . . . . ?
N1 N2 C3 N4 1.3(7) . . . . ?
N1 N2 C3 C7 -178.8(4) . . . . ?
C5 N4 C3 N2 -0.2(7) . . . . ?
C5 N4 C3 C7 179.9(4) . . . . ?
C3 N4 C5 C6 -0.8(7) . . . . ?
N2 N1 C6 C5 0.4(8) . . . . ?
N4 C5 C6 N1 0.7(8) . . . . ?
N2 C3 C7 C11A -180.0(3) . . . . ?
N4 C3 C7 C11A -0.1(6) . . . . ?
N2 C3 C7 S8A -0.5(6) . . . . ?
N4 C3 C7 S8A 179.4(3) . . . . ?
S8A C9 C10 C11A 0.0(7) . . . . ?
C10 C9 S8A C7 1.7(5) . . . . ?
C3 C7 S8A C9 177.7(4) . . . . ?
C11A C7 S8A C9 -2.8(3) . . . . ?
C9 C10 C11A C7 -1.7(5) . . . . ?
C3 C7 C11A C10 -177.7(4) . . . . ?
S8A C7 C11A C10 2.9(3) . . . . ?


data_1
_database_code_depnum_ccdc_archive 'CCDC 919467'
_chemical_name_systematic        
;
3-(2,2'-Bithiophen-5-yl)-1,2,4-triazine
;
_chemical_formula_sum            'C11 H7 N3 S2'
_chemical_formula_weight         245.32
_chemical_melting_point          414-416
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_preparation       propan-2-ol
_cell_length_a                   13.4965(5)
_cell_length_b                   6.1169(3)
_cell_length_c                   13.1345(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.157(2)
_cell_angle_gamma                90.00
_cell_volume                     1079.95(8)
_symmetry_space_group_name_H-M   'P 1 21/c 1'
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_formula_units_Z            4
_exptl_crystal_density_diffrn    1.509
_cell_measurement_temperature    293(2)
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_obs          0.0440
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_obs         0.1195
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
S8 S 0.62056(4) 0.02779(8) 0.86100(4) 0.0393(2) Uani 1 1 d . . .
S13 S 0.89978(5) 0.37487(12) 0.91860(6) 0.0681(3) Uani 1 1 d . . .
N1 N 0.25624(14) 0.1768(4) 0.87995(16) 0.0537(5) Uani 1 1 d . . .
N2 N 0.34834(14) 0.2567(3) 0.87752(14) 0.0472(5) Uani 1 1 d . . .
N4 N 0.41472(13) -0.1049(3) 0.87185(12) 0.0401(4) Uani 1 1 d . . .
C3 C 0.42333(15) 0.1156(3) 0.87420(13) 0.0370(4) Uani 1 1 d . . .
C5 C 0.32418(16) -0.1804(4) 0.87367(15) 0.0442(5) Uani 1 1 d . . .
H5 H 0.3131 -0.3305 0.8721 0.066 Uiso 1 1 calc R . .
C6 C 0.24462(17) -0.0380(4) 0.87798(19) 0.0517(6) Uani 1 1 d . . .
H6 H 0.1810 -0.0955 0.8795 0.077 Uiso 1 1 calc R . .
C7 C 0.52303(15) 0.2044(3) 0.87450(14) 0.0378(4) Uani 1 1 d . . .
C9 C 0.70583(16) 0.2374(3) 0.87441(15) 0.0396(5) Uani 1 1 d . . .
C10 C 0.66000(16) 0.4339(4) 0.88904(17) 0.0440(5) Uani 1 1 d . . .
H10 H 0.6941 0.5655 0.8983 0.066 Uiso 1 1 calc R . .
C11 C 0.55650(16) 0.4151(3) 0.88852(16) 0.0430(5) Uani 1 1 d . . .
H11 H 0.5147 0.5334 0.8968 0.064 Uiso 1 1 calc R . .
C12 C 0.81118(15) 0.1931(4) 0.87003(16) 0.0426(5) Uani 1 1 d . . .
C14 C 0.99435(19) 0.2127(5) 0.8864(2) 0.0656(7) Uani 1 1 d . . .
H14 H 1.0614 0.2474 0.8991 0.098 Uiso 1 1 calc R . .
C15 C 0.9604(2) 0.0288(5) 0.8405(2) 0.0705(8) Uani 1 1 d . . .
H15 H 1.0019 -0.0781 0.8175 0.106 Uiso 1 1 calc R . .
C16 C 0.85474(18) 0.0117(5) 0.8302(2) 0.0610(7) Uani 1 1 d . . .
H16 H 0.8197 -0.1064 0.8005 0.091 Uiso 1 1 calc R . .
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
S8 0.0419(3) 0.0281(3) 0.0478(3) -0.00322(18) 0.0043(2) 0.00512(18)
S13 0.0512(4) 0.0558(5) 0.0972(5) -0.0222(4) 0.0065(3) -0.0075(3)
N1 0.0438(10) 0.0484(12) 0.0694(12) 0.0110(10) 0.0076(9) 0.0105(9)
N2 0.0456(9) 0.0380(10) 0.0588(11) 0.0062(8) 0.0088(8) 0.0105(8)
N4 0.0464(9) 0.0337(9) 0.0401(9) -0.0002(7) 0.0035(7) 0.0057(7)
C3 0.0456(10) 0.0335(10) 0.0321(9) 0.0029(7) 0.0040(7) 0.0077(8)
C5 0.0508(12) 0.0385(11) 0.0427(10) 0.0009(8) 0.0012(8) 0.0019(9)
C6 0.0436(12) 0.0511(14) 0.0597(13) 0.0072(11) 0.0017(10) 0.0022(10)
C7 0.0455(11) 0.0313(10) 0.0366(9) 0.0021(8) 0.0044(8) 0.0101(8)
C9 0.0473(11) 0.0324(10) 0.0389(10) -0.0010(8) 0.0024(8) 0.0027(8)
C10 0.0500(12) 0.0300(10) 0.0522(11) -0.0028(9) 0.0050(9) 0.0008(9)
C11 0.0501(11) 0.0300(10) 0.0494(11) -0.0006(8) 0.0071(9) 0.0082(9)
C12 0.0452(11) 0.0384(11) 0.0438(10) -0.0017(8) 0.0017(8) -0.0010(9)
C14 0.0428(12) 0.0735(19) 0.0802(18) -0.0068(14) 0.0043(11) -0.0014(12)
C15 0.0464(14) 0.074(2) 0.090(2) -0.0213(16) 0.0039(13) 0.0129(13)
C16 0.0416(12) 0.0585(16) 0.0818(18) -0.0203(13) 0.0004(11) 0.0063(11)
_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
S8 C9 1.721(2) . ?
S8 C7 1.7243(19) . ?
S13 C14 1.700(3) . ?
S13 C12 1.713(2) . ?
N1 C6 1.323(3) . ?
N1 N2 1.339(3) . ?
N2 C3 1.334(3) . ?
N4 C5 1.309(3) . ?
N4 C3 1.354(3) . ?
C3 C7 1.451(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.372(3) . ?
C9 C10 1.373(3) . ?
C9 C12 1.454(3) . ?
C10 C11 1.401(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C16 1.381(3) . ?
C14 C15 1.337(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.423(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
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
C9 S8 C7 91.85(10) . . ?
C14 S13 C12 92.47(12) . . ?
C6 N1 N2 118.08(19) . . ?
C3 N2 N1 118.27(19) . . ?
C5 N4 C3 115.45(18) . . ?
N2 C3 N4 125.56(19) . . ?
N2 C3 C7 117.65(18) . . ?
N4 C3 C7 116.79(17) . . ?
N4 C5 C6 120.4(2) . . ?
N4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N1 C6 C5 122.2(2) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C11 C7 C3 130.24(18) . . ?
C11 C7 S8 110.92(16) . . ?
C3 C7 S8 118.78(15) . . ?
C10 C9 C12 128.5(2) . . ?
C10 C9 S8 111.15(16) . . ?
C12 C9 S8 120.30(16) . . ?
C9 C10 C11 112.9(2) . . ?
C9 C10 H10 123.6 . . ?
C11 C10 H10 123.6 . . ?
C7 C11 C10 113.19(19) . . ?
C7 C11 H11 123.4 . . ?
C10 C11 H11 123.4 . . ?
C16 C12 C9 128.0(2) . . ?
C16 C12 S13 110.86(17) . . ?
C9 C12 S13 121.12(16) . . ?
C15 C14 S13 111.6(2) . . ?
C15 C14 H14 124.2 . . ?
S13 C14 H14 124.2 . . ?
C14 C15 C16 113.9(3) . . ?
C14 C15 H15 123.0 . . ?
C16 C15 H15 123.0 . . ?
C12 C16 C15 111.2(2) . . ?
C12 C16 H16 124.4 . . ?
C15 C16 H16 124.4 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C3 -0.6(3) . . . . ?
N1 N2 C3 N4 0.8(3) . . . . ?
N1 N2 C3 C7 -178.30(18) . . . . ?
C5 N4 C3 N2 -0.4(3) . . . . ?
C5 N4 C3 C7 178.71(16) . . . . ?
C3 N4 C5 C6 -0.1(3) . . . . ?
N2 N1 C6 C5 0.1(4) . . . . ?
N4 C5 C6 N1 0.3(3) . . . . ?
N2 C3 C7 C11 7.8(3) . . . . ?
N4 C3 C7 C11 -171.4(2) . . . . ?
N2 C3 C7 S8 -175.39(14) . . . . ?
N4 C3 C7 S8 5.4(2) . . . . ?
C9 S8 C7 C11 0.08(16) . . . . ?
C9 S8 C7 C3 -177.35(15) . . . . ?
C7 S8 C9 C10 0.25(17) . . . . ?
C7 S8 C9 C12 179.97(17) . . . . ?
C12 C9 C10 C11 179.8(2) . . . . ?
S8 C9 C10 C11 -0.5(2) . . . . ?
C3 C7 C11 C10 176.66(19) . . . . ?
S8 C7 C11 C10 -0.4(2) . . . . ?
C9 C10 C11 C7 0.6(3) . . . . ?
C10 C9 C12 C16 -161.8(3) . . . . ?
S8 C9 C12 C16 18.5(3) . . . . ?
C10 C9 C12 S13 18.8(3) . . . . ?
S8 C9 C12 S13 -160.90(12) . . . . ?
C14 S13 C12 C16 0.1(2) . . . . ?
C14 S13 C12 C9 179.6(2) . . . . ?
C12 S13 C14 C15 0.2(3) . . . . ?
S13 C14 C15 C16 -0.4(4) . . . . ?
C9 C12 C16 C15 -179.8(2) . . . . ?
S13 C12 C16 C15 -0.3(3) . . . . ?
C14 C15 C16 C12 0.5(4) . . . . ?