4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C₁₃H₁₀N₄S, the almost ideally planar triazole ring forms dihedral angles of 58.5 (1) and 36.9 (1)° with the phenyl and pyridine planes, respectively. The planes of the phenyl and pyridyl substituents form a dihedral angle of 58.5 (1)° with each other. The crystal packing is stabilized by intermolecular N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.076
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C1      ..       5.88 su

   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

   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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Crystal data

C13H10N4S	F(000) = 1056
Mr = 254.32	Dx = 1.336 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2731 reflections
a = 11.2958 (6) Å	θ = 1.6–27.2°
b = 12.7480 (8) Å	µ = 0.24 mm^−1
c = 17.5607 (8) Å	T = 296 K
V = 2528.7 (2) Å^3	Prism, yellow
Z = 8	0.50 × 0.42 × 0.15 mm

Data collection

Stoe IPDS-II diffractometer	2731 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1779 reflections with I > 2σ(I
Plane graphite monochromator	Rint = 0.067
Detector resolution: 6.67 pixels mm^-1	θmax = 27.2°, θmin = 2.3°
ω scans	h = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.915, Tmax = 0.947	l = −22→22
23863 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0422P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.001
2731 reflections	Δρmax = 0.16 e Å^−3
164 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (8)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² or ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F²,conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.06585 (5)	0.27073 (3)	0.63327 (2)	0.0590 (1)
N1	0.14814 (12)	0.08338 (9)	0.58496 (6)	0.0487 (4)
N2	0.17094 (12)	0.02542 (9)	0.52092 (6)	0.0477 (4)
N3	0.10462 (11)	0.18385 (8)	0.49209 (6)	0.0416 (3)
N4	0.18177 (13)	−0.00508 (10)	0.23423 (7)	0.0547 (4)
C1	0.10752 (14)	0.18002 (11)	0.57081 (7)	0.0441 (4)
C2	0.14414 (13)	0.08834 (10)	0.46547 (7)	0.0410 (4)
C3	0.15792 (13)	0.05845 (10)	0.38488 (7)	0.0413 (4)
C4	0.13490 (13)	−0.04334 (11)	0.36334 (7)	0.0461 (5)
C5	0.14662 (15)	−0.07144 (12)	0.28841 (8)	0.0525 (5)
C6	0.20807 (16)	0.09208 (12)	0.25568 (8)	0.0578 (5)
C7	0.19641 (16)	0.12778 (12)	0.32956 (8)	0.0535 (5)
C8	0.05342 (13)	0.26765 (10)	0.44820 (7)	0.0422 (4)
C9	−0.04240 (15)	0.24628 (12)	0.40202 (10)	0.0581 (5)
C10	−0.08924 (18)	0.32622 (15)	0.35869 (11)	0.0710 (7)
C11	−0.04268 (18)	0.42544 (14)	0.36251 (11)	0.0685 (7)
C12	0.05058 (16)	0.44617 (12)	0.41024 (10)	0.0608 (6)
C13	0.10026 (15)	0.36691 (11)	0.45305 (8)	0.0501 (5)
H1	0.15900	0.05970	0.63030	0.0580*
H4	0.11160	−0.09270	0.39940	0.0550*
H5	0.12920	−0.14020	0.27470	0.0630*
H6	0.23580	0.13860	0.21900	0.0690*
H7	0.21410	0.19700	0.34190	0.0640*
H9	−0.07470	0.17920	0.40020	0.0700*
H10	−0.15290	0.31280	0.32660	0.0850*
H11	−0.07440	0.47880	0.33270	0.0820*
H12	0.08040	0.51400	0.41370	0.0730*
H13	0.16450	0.38040	0.48470	0.0600*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0878 (3)	0.0474 (2)	0.0417 (2)	0.0004 (2)	0.0067 (2)	−0.0092 (2)
N1	0.0689 (8)	0.0485 (7)	0.0288 (5)	0.0048 (6)	0.0011 (5)	0.0003 (5)
N2	0.0628 (8)	0.0471 (6)	0.0333 (5)	0.0064 (6)	0.0017 (5)	−0.0013 (5)
N3	0.0528 (7)	0.0398 (6)	0.0322 (5)	−0.0008 (5)	−0.0002 (5)	−0.0009 (4)
N4	0.0692 (9)	0.0597 (8)	0.0353 (6)	0.0000 (6)	0.0027 (6)	−0.0043 (5)
C1	0.0542 (9)	0.0449 (7)	0.0331 (7)	−0.0047 (6)	0.0009 (6)	−0.0003 (5)
C2	0.0503 (8)	0.0400 (7)	0.0328 (6)	0.0009 (6)	−0.0001 (6)	−0.0009 (5)
C3	0.0471 (8)	0.0440 (7)	0.0327 (6)	0.0022 (6)	−0.0009 (6)	−0.0006 (5)
C4	0.0540 (9)	0.0476 (8)	0.0366 (7)	−0.0018 (7)	0.0014 (6)	0.0000 (6)
C5	0.0642 (10)	0.0515 (8)	0.0418 (7)	−0.0048 (7)	0.0001 (7)	−0.0085 (6)
C6	0.0802 (11)	0.0548 (9)	0.0385 (7)	−0.0013 (8)	0.0100 (8)	0.0048 (7)
C7	0.0758 (11)	0.0443 (8)	0.0405 (7)	−0.0060 (7)	0.0071 (7)	−0.0004 (6)
C8	0.0482 (8)	0.0407 (6)	0.0377 (6)	0.0014 (6)	0.0008 (6)	0.0007 (5)
C9	0.0612 (10)	0.0464 (8)	0.0666 (10)	−0.0002 (7)	−0.0142 (8)	−0.0055 (7)
C10	0.0705 (12)	0.0628 (11)	0.0797 (12)	0.0089 (9)	−0.0315 (10)	−0.0039 (8)
C11	0.0754 (13)	0.0542 (10)	0.0760 (11)	0.0142 (9)	−0.0120 (9)	0.0114 (8)
C12	0.0674 (11)	0.0424 (8)	0.0725 (10)	−0.0018 (8)	0.0017 (9)	0.0078 (7)
C13	0.0533 (9)	0.0461 (8)	0.0508 (8)	−0.0046 (7)	−0.0021 (7)	0.0010 (6)

Geometric parameters (Å, º)

S1—C1	1.6619 (14)	C8—C13	1.374 (2)
N1—N2	1.3700 (15)	C8—C9	1.380 (2)
N1—C1	1.3379 (18)	C9—C10	1.378 (3)
N2—C2	1.2974 (17)	C10—C11	1.372 (3)
N3—C1	1.3836 (16)	C11—C12	1.372 (3)
N3—C2	1.3785 (17)	C12—C13	1.379 (2)
N3—C8	1.4387 (17)	C4—H4	0.93
N4—C5	1.334 (2)	C5—H5	0.93
N4—C6	1.328 (2)	C6—H6	0.93
N1—H1	0.86	C7—H7	0.93
C2—C3	1.4739 (17)	C9—H9	0.93
C3—C7	1.383 (2)	C10—H10	0.93
C3—C4	1.3764 (19)	C11—H11	0.93
C4—C5	1.3701 (19)	C12—H12	0.93
C6—C7	1.381 (2)	C13—H13	0.93
S1···C13	3.4162 (15)	C10···N1^viii	3.333 (2)
S1···C4^i	3.6808 (15)	C13···S1	3.4162 (15)
S1···H13	3.1628	C13···C4^ix	3.569 (2)
S1···H6^ii	2.9364	C1···H4^i	2.7639
S1···H4^i	3.0818	C1···H13	3.0374
S1···H5^i	3.1992	C2···H9	2.9607
S1···H5^iii	3.0740	C3···H9	3.0572
N1···N3	2.1312 (15)	C3···H12^vi	3.0520
N1···C10^iv	3.333 (2)	C5···H1^v	2.7841
N1···C4^i	3.363 (2)	C6···H1^v	2.9831
N1···N4^iii	2.8305 (16)	C8···H7	2.7550
N2···N3	2.2128 (16)	H1···N4^iii	1.9703
N3···N2	2.2128 (16)	H1···C5^iii	2.7841
N4···N1^v	2.8305 (16)	H1···C6^iii	2.9831
N1···H4^i	2.9492	H4···N2	2.6964
N2···H4	2.6964	H4···S1^i	3.0818
N2···H13^vi	2.6977	H4···N1^i	2.9492
N3···H7	2.9178	H4···C1^i	2.7639
N4···H1^v	1.9703	H5···S1^i	3.1992
C1···C4^i	3.446 (2)	H5···S1^v	3.0740
C3···C9	3.308 (2)	H6···S1^x	2.9364
C4···S1^i	3.6808 (15)	H6···H10^vii	2.5396
C4···C1^i	3.446 (2)	H7···N3	2.9178
C4···C13^vi	3.569 (2)	H7···C8	2.7550
C4···N1^i	3.363 (2)	H9···C2	2.9607
C5···C5^vii	3.577 (2)	H9···C3	3.0572
C7···C9	3.343 (2)	H10···H6^vii	2.5396
C7···C8	3.183 (2)	H12···C3^ix	3.0520
C8···C7	3.183 (2)	H13···S1	3.1628
C9···C3	3.308 (2)	H13···C1	3.0374
C9···C7	3.343 (2)	H13···N2^ix	2.6977
N2—N1—C1	114.12 (10)	C8—C9—C10	118.68 (15)
N1—N2—C2	103.82 (11)	C9—C10—C11	120.53 (18)
C1—N3—C2	107.46 (11)	C10—C11—C12	120.13 (17)
C1—N3—C8	124.82 (11)	C11—C12—C13	120.30 (15)
C2—N3—C8	127.18 (11)	C8—C13—C12	118.97 (15)
C5—N4—C6	117.12 (13)	C3—C4—H4	120.2
C1—N1—H1	122.9	C5—C4—H4	120.3
N2—N1—H1	122.9	N4—C5—H5	118.4
S1—C1—N3	128.91 (11)	C4—C5—H5	118.3
N1—C1—N3	103.07 (11)	N4—C6—H6	118.3
S1—C1—N1	127.97 (10)	C7—C6—H6	118.2
N3—C2—C3	126.03 (11)	C3—C7—H7	120.7
N2—C2—N3	111.54 (11)	C6—C7—H7	120.7
N2—C2—C3	122.43 (12)	C8—C9—H9	120.6
C4—C3—C7	117.95 (12)	C10—C9—H9	120.7
C2—C3—C7	122.84 (12)	C9—C10—H10	119.7
C2—C3—C4	119.19 (11)	C11—C10—H10	119.7
C3—C4—C5	119.48 (13)	C10—C11—H11	119.9
N4—C5—C4	123.24 (14)	C12—C11—H11	119.9
N4—C6—C7	123.53 (14)	C11—C12—H12	119.8
C3—C7—C6	118.62 (14)	C13—C12—H12	119.9
N3—C8—C9	118.93 (12)	C8—C13—H13	120.5
C9—C8—C13	121.35 (13)	C12—C13—H13	120.5
N3—C8—C13	119.72 (13)
C1—N1—N2—C2	0.31 (17)	C5—N4—C6—C7	−2.6 (3)
N2—N1—C1—S1	177.60 (12)	N2—C2—C3—C7	−141.88 (16)
N2—N1—C1—N3	−0.18 (17)	N2—C2—C3—C4	36.3 (2)
N1—N2—C2—N3	−0.31 (16)	N3—C2—C3—C7	36.9 (2)
N1—N2—C2—C3	178.63 (13)	C2—C3—C7—C6	179.14 (15)
C2—N3—C1—S1	−177.77 (12)	C7—C3—C4—C5	−2.3 (2)
C8—N3—C1—N1	172.03 (13)	C4—C3—C7—C6	1.0 (2)
C8—N3—C1—S1	−5.7 (2)	C2—C3—C4—C5	179.48 (14)
C2—N3—C1—N1	−0.03 (16)	C3—C4—C5—N4	1.3 (2)
C1—N3—C2—N2	0.22 (17)	N4—C6—C7—C3	1.6 (3)
C8—N3—C2—N2	−171.59 (13)	N3—C8—C9—C10	−178.42 (15)
C1—N3—C2—C3	−178.68 (14)	C13—C8—C9—C10	1.7 (2)
C8—N3—C2—C3	9.5 (2)	N3—C8—C13—C12	179.60 (14)
C2—N3—C8—C13	−126.34 (15)	C9—C8—C13—C12	−0.5 (2)
C1—N3—C8—C13	63.19 (19)	C8—C9—C10—C11	−1.1 (3)
C1—N3—C8—C9	−116.69 (16)	C9—C10—C11—C12	−0.6 (3)
C2—N3—C8—C9	53.8 (2)	C10—C11—C12—C13	1.8 (3)
C6—N4—C5—C4	1.2 (2)	C11—C12—C13—C8	−1.3 (3)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x, −y, z+1/2; (iv) x+1/2, −y+1/2, −z+1; (v) x, −y, z−1/2; (vi) −x+1/2, y−1/2, z; (vii) −x, y, −z+1/2; (viii) x−1/2, −y+1/2, −z+1; (ix) −x+1/2, y+1/2, z; (x) −x+1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4^iii	0.86	1.97	2.8305 (16)	179

Symmetry code: (iii) x, −y, z+1/2.