1,3-Thia­zole-4-carbo­nitrile

The title compound, C₄H₂N₂S, is a 1,3-thia­zole substituted in the 4-position by a nitrile group. In the crystal, C—H...N hydrogen bonds and aromatic π–π stacking inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        89% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 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
   1 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

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2015) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

1,3-Thiazole-4-carbonitrile

Crystal data

C4H2N2S	F(000) = 224
Mr = 110.14	Dx = 1.536 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 3.7924 (3) Å	Cell parameters from 2588 reflections
b = 19.8932 (18) Å	θ = 4.5–66.7°
c = 6.3155 (5) Å	µ = 4.77 mm^−1
β = 91.084 (6)°	T = 150 K
V = 476.37 (7) Å^3	Plate, colourless
Z = 4	0.24 × 0.18 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	854 independent reflections
Radiation source: microfocus	783 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.040
Detector resolution: 8.3333 pixels mm^-1	θmax = 66.7°, θmin = 4.5°
φ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −23→23
Tmin = 0.40, Tmax = 0.71	l = −7→7
4709 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0638P)^2 + 0.0618P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
854 reflections	Δρmax = 0.32 e Å^−3
64 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8382 (4)	0.61784 (9)	0.5796 (3)	0.0306 (4)
C2	0.8897 (5)	0.59416 (9)	0.7795 (3)	0.0360 (4)
H2	0.838664	0.549800	0.825466	0.043*
C3	1.0479 (5)	0.70963 (10)	0.7216 (3)	0.0388 (5)
H3	1.124522	0.755015	0.731394	0.047*
C4	0.6933 (5)	0.57919 (9)	0.4057 (3)	0.0350 (4)
N1	0.9271 (4)	0.68396 (9)	0.5450 (3)	0.0400 (4)
N2	0.5794 (5)	0.54939 (9)	0.2660 (3)	0.0450 (4)
S1	1.06029 (11)	0.65664 (2)	0.93452 (7)	0.0367 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0280 (7)	0.0334 (9)	0.0306 (9)	0.0004 (7)	0.0030 (6)	0.0000 (6)
C2	0.0424 (10)	0.0352 (9)	0.0304 (9)	0.0020 (7)	0.0011 (7)	0.0000 (7)
C3	0.0400 (9)	0.0378 (9)	0.0383 (11)	−0.0060 (7)	−0.0022 (8)	0.0015 (7)
C4	0.0381 (9)	0.0364 (9)	0.0305 (9)	−0.0020 (7)	0.0040 (7)	0.0031 (7)
N1	0.0480 (10)	0.0372 (10)	0.0346 (9)	−0.0069 (6)	−0.0029 (7)	0.0049 (6)
N2	0.0559 (10)	0.0455 (9)	0.0336 (9)	−0.0102 (8)	0.0000 (7)	−0.0022 (7)
S1	0.0380 (3)	0.0426 (3)	0.0294 (3)	0.00213 (16)	−0.0020 (2)	−0.00236 (15)

Geometric parameters (Å, º)

C1—C2	1.358 (3)	C3—N1	1.302 (3)
C1—N1	1.376 (3)	C3—S1	1.7089 (19)
C1—C4	1.441 (3)	C3—H3	0.9500
C2—S1	1.7024 (19)	C4—N2	1.141 (3)
C2—H2	0.9500
C2—C1—N1	116.58 (16)	N1—C3—S1	115.85 (15)
C2—C1—C4	124.71 (17)	N1—C3—H3	122.1
N1—C1—C4	118.70 (16)	S1—C3—H3	122.1
C1—C2—S1	109.13 (14)	N2—C4—C1	178.96 (19)
C1—C2—H2	125.4	C3—N1—C1	108.81 (16)
S1—C2—H2	125.4	C2—S1—C3	89.62 (9)
N1—C1—C2—S1	−0.4 (2)	C4—C1—N1—C3	179.24 (16)
C4—C1—C2—S1	−179.26 (14)	C1—C2—S1—C3	0.28 (15)
S1—C3—N1—C1	−0.1 (2)	N1—C3—S1—C2	−0.12 (16)
C2—C1—N1—C3	0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2^i	0.95	2.59	3.374 (2)	140
C3—H3···N1^ii	0.95	2.57	3.257 (2)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2.