Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046673/dn2232sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046673/dn2232Isup2.hkl |
CCDC reference: 663848
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.101
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, C10H9N7S2, was synthesized via the reflux reaction of 2-aminothiazole (10.711 g, 0.1 mol) and 2-pyridylaldehyde (10.113 g, 0.1 mol) in 1:1 stoichiometry in 200 ml me thanol solution with 1 ml HCl (6 M) for 24 h. The block crystals suitable for single-crystal X-ray diffraction were obtained via recrystallization of the powder in methanol at room temperature.
All H atoms attached to C and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).
The molecule of the title compound consists of two aminothiazolyl and two pyridyl groups linked by a C═C double bond which lies on a crystallographic centre of symmetry (Fig. 1).
The adjacent molecules are linked by N3—H3A···S1i (Table 1) hydrogen bonds to generate a one dimensional supramolecular network strcucture (Fig. 2). There are no aromatic π–π stacking interactions.
[Please provide at least one reference to related literature]
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1999).
C16H12N8S2 | Z = 1 |
Mr = 380.46 | F(000) = 196 |
Triclinic, P1 | Dx = 1.551 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4720 (11) Å | Cell parameters from 4677 reflections |
b = 7.9623 (16) Å | θ = 3.4–27.5° |
c = 9.7363 (19) Å | µ = 0.35 mm−1 |
α = 91.01 (3)° | T = 153 K |
β = 93.96 (3)° | Block, colourless |
γ = 105.57 (3)° | 0.20 × 0.18 × 0.14 mm |
V = 407.38 (15) Å3 |
Bruker P4 diffractometer | 1447 independent reflections |
Radiation source: fine-focus sealed tube | 1032 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 25.2°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.926, Tmax = 0.943 | k = −9→9 |
2787 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0547P)2 + 0.0338P] where P = (Fo2 + 2Fc2)/3 |
1447 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C16H12N8S2 | γ = 105.57 (3)° |
Mr = 380.46 | V = 407.38 (15) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.4720 (11) Å | Mo Kα radiation |
b = 7.9623 (16) Å | µ = 0.35 mm−1 |
c = 9.7363 (19) Å | T = 153 K |
α = 91.01 (3)° | 0.20 × 0.18 × 0.14 mm |
β = 93.96 (3)° |
Bruker P4 diffractometer | 1447 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1032 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 0.943 | Rint = 0.024 |
2787 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.34 e Å−3 |
1447 reflections | Δρmin = −0.42 e Å−3 |
118 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7059 (5) | 0.2732 (3) | 0.9578 (3) | 0.0497 (7) | |
H1 | 0.8187 | 0.2333 | 1.0159 | 0.060* | |
C2 | 0.4851 (4) | 0.3957 (3) | 0.7878 (2) | 0.0314 (5) | |
C3 | 0.5411 (4) | 0.5333 (3) | 0.5653 (2) | 0.0312 (5) | |
C4 | 0.7705 (4) | 0.6802 (3) | 0.6017 (2) | 0.0317 (5) | |
N4 | 0.9649 (3) | 0.7030 (3) | 0.5189 (2) | 0.0363 (5) | |
C5 | 1.1725 (4) | 0.8343 (3) | 0.5528 (3) | 0.0423 (6) | |
H5 | 1.3071 | 0.8511 | 0.4966 | 0.051* | |
C6 | 1.1987 (5) | 0.9445 (3) | 0.6642 (3) | 0.0463 (7) | |
H6 | 1.3481 | 1.0327 | 0.6842 | 0.056* | |
C7 | 0.9988 (5) | 0.9226 (3) | 0.7473 (3) | 0.0452 (7) | |
H7 | 1.0098 | 0.9973 | 0.8233 | 0.054* | |
N1 | 0.4702 (4) | 0.2465 (3) | 0.9794 (2) | 0.0489 (6) | |
N2 | 0.3381 (4) | 0.3183 (3) | 0.8806 (2) | 0.0405 (5) | |
N3 | 0.3944 (3) | 0.4696 (3) | 0.67620 (18) | 0.0348 (5) | |
H3 | 0.2404 | 0.4775 | 0.6737 | 0.042* | |
C8 | 0.7827 (4) | 0.7882 (3) | 0.7156 (2) | 0.0386 (6) | |
H8 | 0.6462 | 0.7705 | 0.7705 | 0.046* | |
S1 | 0.79840 (11) | 0.38809 (9) | 0.81359 (7) | 0.0459 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0555 (17) | 0.0585 (18) | 0.0389 (15) | 0.0214 (14) | 0.0033 (13) | 0.0134 (13) |
C2 | 0.0307 (12) | 0.0341 (13) | 0.0278 (12) | 0.0059 (10) | 0.0037 (10) | −0.0023 (10) |
C3 | 0.0262 (11) | 0.0370 (14) | 0.0317 (11) | 0.0102 (10) | 0.0042 (9) | 0.0053 (10) |
C4 | 0.0284 (12) | 0.0354 (14) | 0.0313 (13) | 0.0087 (10) | 0.0006 (10) | 0.0078 (10) |
N4 | 0.0277 (10) | 0.0418 (12) | 0.0378 (11) | 0.0064 (9) | 0.0041 (9) | 0.0044 (9) |
C5 | 0.0292 (12) | 0.0432 (15) | 0.0507 (16) | 0.0024 (11) | 0.0057 (11) | 0.0040 (13) |
C6 | 0.0378 (14) | 0.0378 (15) | 0.0573 (18) | 0.0015 (11) | −0.0024 (13) | 0.0002 (14) |
C7 | 0.0497 (15) | 0.0376 (15) | 0.0447 (15) | 0.0070 (12) | −0.0012 (13) | −0.0038 (12) |
N1 | 0.0583 (15) | 0.0548 (14) | 0.0349 (12) | 0.0153 (11) | 0.0095 (10) | 0.0140 (10) |
N2 | 0.0397 (11) | 0.0457 (13) | 0.0354 (11) | 0.0076 (9) | 0.0112 (9) | 0.0076 (10) |
N3 | 0.0263 (10) | 0.0490 (13) | 0.0300 (10) | 0.0102 (9) | 0.0060 (8) | 0.0077 (9) |
C8 | 0.0385 (14) | 0.0432 (15) | 0.0341 (14) | 0.0103 (11) | 0.0053 (11) | 0.0019 (12) |
S1 | 0.0346 (4) | 0.0632 (5) | 0.0426 (4) | 0.0163 (3) | 0.0060 (3) | 0.0156 (3) |
C1—N1 | 1.283 (3) | N4—C5 | 1.338 (3) |
C1—S1 | 1.720 (3) | C5—C6 | 1.358 (4) |
C1—H1 | 0.9300 | C5—H5 | 0.9300 |
C2—N2 | 1.303 (3) | C6—C7 | 1.380 (4) |
C2—N3 | 1.370 (3) | C6—H6 | 0.9300 |
C2—S1 | 1.733 (2) | C7—C8 | 1.378 (3) |
C3—C3i | 1.367 (4) | C7—H7 | 0.9300 |
C3—N3 | 1.410 (3) | N1—N2 | 1.386 (3) |
C3—C4 | 1.485 (3) | N3—H3 | 0.8600 |
C4—N4 | 1.354 (3) | C8—H8 | 0.9300 |
C4—C8 | 1.378 (3) | ||
N1—C1—S1 | 115.2 (2) | C5—C6—C7 | 118.6 (2) |
N1—C1—H1 | 122.4 | C5—C6—H6 | 120.7 |
S1—C1—H1 | 122.4 | C7—C6—H6 | 120.7 |
N2—C2—N3 | 122.2 (2) | C8—C7—C6 | 118.8 (2) |
N2—C2—S1 | 114.43 (18) | C8—C7—H7 | 120.6 |
N3—C2—S1 | 123.33 (16) | C6—C7—H7 | 120.6 |
C3i—C3—N3 | 119.7 (2) | C1—N1—N2 | 112.67 (19) |
C3i—C3—C4 | 125.0 (2) | C2—N2—N1 | 111.6 (2) |
N3—C3—C4 | 115.10 (19) | C2—N3—C3 | 123.21 (19) |
N4—C4—C8 | 121.9 (2) | C2—N3—H3 | 118.4 |
N4—C4—C3 | 117.4 (2) | C3—N3—H3 | 118.4 |
C8—C4—C3 | 120.74 (19) | C4—C8—C7 | 119.4 (2) |
C5—N4—C4 | 117.3 (2) | C4—C8—H8 | 120.3 |
N4—C5—C6 | 124.0 (2) | C7—C8—H8 | 120.3 |
N4—C5—H5 | 118.0 | C1—S1—C2 | 86.18 (12) |
C6—C5—H5 | 118.0 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···S1ii | 0.86 | 2.79 | 3.513 (2) | 143 |
Symmetry code: (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H12N8S2 |
Mr | 380.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 153 |
a, b, c (Å) | 5.4720 (11), 7.9623 (16), 9.7363 (19) |
α, β, γ (°) | 91.01 (3), 93.96 (3), 105.57 (3) |
V (Å3) | 407.38 (15) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.20 × 0.18 × 0.14 |
Data collection | |
Diffractometer | Bruker P4 |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.926, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2787, 1447, 1032 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.02 |
No. of reflections | 1447 |
No. of parameters | 118 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.42 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), SHELXTL (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···S1i | 0.86 | 2.79 | 3.513 (2) | 142.9 |
Symmetry code: (i) x−1, y, z. |
The molecule of the title compound consists of two aminothiazolyl and two pyridyl groups linked by a C═C double bond which lies on a crystallographic centre of symmetry (Fig. 1).
The adjacent molecules are linked by N3—H3A···S1i (Table 1) hydrogen bonds to generate a one dimensional supramolecular network strcucture (Fig. 2). There are no aromatic π–π stacking interactions.