4-(2-Pyridylmethyl­eneamino)-3-(2-thienylmeth­yl)-1H-1,2,4-triazol-5(4H)-one

Yılmaz, I.; Arslan, N.B.; Kazak, C.; Sancak, K.; Unver, Y.

doi:10.1107/S1600536806023981

4-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

I. Yılmaz, N. B. Arslan, C. Kazak, K. Sancak and Y. Unver

In the title compound, C₁₃H₁₁N₅OS, molecules are linked into centrosymmetric dimers through intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023981/bh2022sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023981/bh2022Isup2.hkl Contains datablock I

CCDC reference: 613576

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.107
Data-to-parameter ratio = 14.1

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No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one top

Crystal data top

C₁₃H₁₁N₅OS	F(000) = 592
M_r = 285.33	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15109 reflections
a = 5.6726 (4) Å	θ = 1.6–27.6°
b = 18.3669 (11) Å	µ = 0.25 mm⁻¹
c = 12.5690 (9) Å	T = 293 K
β = 92.651 (6)°	Prism, colourless
V = 1308.14 (15) Å³	0.48 × 0.20 × 0.02 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	1785 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
rotation method scans	h = −6→6
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −20→22
T_min = 0.910, T_max = 0.988	l = −15→15
13756 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0622P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2564 reflections	Δρ_max = 0.28 e Å⁻³
182 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (19)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0296 (5)	0.35978 (14)	0.7881 (2)	0.0443 (7)
H1	−0.0987	0.3858	0.7592	0.053*
C2	0.2179 (4)	0.34060 (13)	0.73282 (19)	0.0366 (6)
H2	0.2323	0.3521	0.6614	0.044*
C3	0.3951 (4)	0.30057 (11)	0.79478 (16)	0.0277 (5)
H3	0.5359	0.2833	0.7693	0.033*
C4	0.3223 (4)	0.29174 (12)	0.89947 (17)	0.0295 (5)
C5	0.4456 (4)	0.24959 (12)	0.98867 (17)	0.0312 (5)
H5A	0.6122	0.2456	0.9755	0.037*
H5B	0.4304	0.2755	1.0553	0.037*
C6	0.3429 (4)	0.17565 (12)	0.99748 (16)	0.0269 (5)
C7	0.2684 (4)	0.05795 (12)	0.96098 (16)	0.0267 (5)
C8	0.6554 (4)	0.06498 (12)	0.82050 (16)	0.0290 (5)
H8	0.5634	0.0232	0.8244	0.035*
C9	0.8568 (4)	0.06647 (12)	0.75151 (16)	0.0279 (5)
C10	1.0020 (4)	0.12652 (13)	0.74141 (17)	0.0299 (5)
H10	0.9747	0.1693	0.7784	0.036*
C11	1.1888 (4)	0.12105 (14)	0.67478 (18)	0.0339 (6)
H11	1.2902	0.1602	0.6663	0.041*
C12	1.2224 (4)	0.05663 (14)	0.62116 (18)	0.0353 (6)
H12	1.3460	0.0517	0.5756	0.042*
C13	1.0699 (4)	−0.00028 (13)	0.63636 (18)	0.0342 (6)
H13	1.0952	−0.0437	0.6005	0.041*
N1	0.1656 (4)	0.15916 (10)	1.05344 (14)	0.0318 (4)
N2	0.1234 (3)	0.08606 (10)	1.03169 (14)	0.0301 (4)
H6	0.0151	0.0612	1.0607	0.036*
N3	0.4152 (3)	0.11639 (10)	0.93933 (13)	0.0257 (4)
N4	0.6065 (3)	0.12114 (10)	0.87529 (13)	0.0268 (4)
N5	0.8882 (4)	0.00324 (11)	0.69947 (14)	0.0322 (5)
O1	0.2715 (3)	−0.00434 (8)	0.92330 (12)	0.0306 (4)
S1	0.05312 (12)	0.33106 (4)	0.91681 (5)	0.0437 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0366 (15)	0.0327 (14)	0.0629 (17)	−0.0015 (12)	−0.0055 (13)	0.0119 (12)
C2	0.0395 (15)	0.0320 (13)	0.0378 (12)	−0.0091 (11)	−0.0025 (11)	0.0038 (10)
C3	0.0316 (13)	0.0212 (11)	0.0298 (11)	−0.0072 (10)	−0.0042 (9)	−0.0005 (9)
C4	0.0304 (13)	0.0226 (12)	0.0358 (11)	−0.0052 (10)	0.0042 (9)	−0.0021 (9)
C5	0.0357 (13)	0.0265 (12)	0.0313 (11)	−0.0062 (10)	−0.0003 (9)	−0.0031 (9)
C6	0.0304 (12)	0.0252 (12)	0.0248 (10)	−0.0015 (10)	−0.0025 (9)	0.0004 (8)
C7	0.0278 (12)	0.0255 (11)	0.0264 (10)	−0.0023 (9)	−0.0029 (9)	0.0038 (9)
C8	0.0301 (13)	0.0264 (11)	0.0302 (11)	−0.0023 (10)	−0.0015 (9)	0.0050 (9)
C9	0.0282 (12)	0.0277 (12)	0.0272 (10)	0.0021 (10)	−0.0040 (9)	0.0041 (9)
C10	0.0301 (13)	0.0276 (12)	0.0318 (11)	0.0010 (10)	−0.0022 (9)	0.0043 (9)
C11	0.0306 (13)	0.0359 (13)	0.0351 (12)	−0.0025 (11)	−0.0016 (10)	0.0097 (10)
C12	0.0333 (14)	0.0417 (15)	0.0311 (11)	0.0046 (11)	0.0051 (10)	0.0041 (10)
C13	0.0369 (14)	0.0336 (13)	0.0322 (11)	0.0049 (11)	0.0014 (10)	−0.0022 (10)
N1	0.0372 (11)	0.0268 (10)	0.0316 (9)	−0.0048 (9)	0.0023 (8)	−0.0015 (8)
N2	0.0331 (11)	0.0248 (10)	0.0326 (10)	−0.0060 (9)	0.0056 (8)	0.0013 (8)
N3	0.0265 (10)	0.0251 (10)	0.0255 (9)	−0.0031 (8)	0.0002 (7)	0.0014 (7)
N4	0.0258 (10)	0.0284 (10)	0.0260 (9)	−0.0020 (8)	−0.0012 (7)	0.0039 (8)
N5	0.0337 (12)	0.0299 (11)	0.0327 (10)	−0.0002 (9)	−0.0015 (8)	−0.0016 (8)
O1	0.0326 (9)	0.0238 (8)	0.0356 (8)	−0.0039 (7)	0.0022 (7)	0.0014 (7)
S1	0.0386 (4)	0.0374 (4)	0.0559 (4)	0.0021 (3)	0.0118 (3)	0.0019 (3)

Geometric parameters (Å, º) top

C1—C2	1.348 (4)	C8—N4	1.278 (3)
C1—S1	1.701 (3)	C8—C9	1.466 (3)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.444 (3)	C9—N5	1.349 (3)
C2—H2	0.9300	C9—C10	1.386 (3)
C3—C4	1.407 (3)	C10—C11	1.385 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.507 (3)	C11—C12	1.379 (4)
C4—S1	1.712 (2)	C11—H11	0.9300
C5—C6	1.484 (3)	C12—C13	1.376 (4)
C5—H5A	0.9700	C12—H12	0.9300
C5—H5B	0.9700	C13—N5	1.331 (3)
C6—N1	1.290 (3)	C13—H13	0.9300
C6—N3	1.384 (3)	N1—N2	1.389 (3)
C7—O1	1.239 (3)	N2—H6	0.8600
C7—N2	1.341 (3)	N3—N4	1.384 (3)
C7—N3	1.393 (3)

C2—C1—S1	112.3 (2)	C9—C8—H8	120.1
C2—C1—H1	123.8	N5—C9—C10	123.3 (2)
S1—C1—H1	123.8	N5—C9—C8	113.3 (2)
C1—C2—C3	113.8 (2)	C10—C9—C8	123.5 (2)
C1—C2—H2	123.1	C11—C10—C9	118.2 (2)
C3—C2—H2	123.1	C11—C10—H10	120.9
C4—C3—C2	109.6 (2)	C9—C10—H10	120.9
C4—C3—H3	125.2	C12—C11—C10	119.0 (2)
C2—C3—H3	125.2	C12—C11—H11	120.5
C3—C4—C5	127.5 (2)	C10—C11—H11	120.5
C3—C4—S1	111.87 (17)	C13—C12—C11	118.8 (2)
C5—C4—S1	120.50 (17)	C13—C12—H12	120.6
C6—C5—C4	110.82 (18)	C11—C12—H12	120.6
C6—C5—H5A	109.5	N5—C13—C12	123.7 (2)
C4—C5—H5A	109.5	N5—C13—H13	118.1
C6—C5—H5B	109.5	C12—C13—H13	118.1
C4—C5—H5B	109.5	C6—N1—N2	104.55 (18)
H5A—C5—H5B	108.1	C7—N2—N1	113.41 (18)
N1—C6—N3	111.16 (19)	C7—N2—H6	123.3
N1—C6—C5	125.1 (2)	N1—N2—H6	123.3
N3—C6—C5	123.6 (2)	N4—N3—C6	121.16 (18)
O1—C7—N2	129.0 (2)	N4—N3—C7	130.87 (18)
O1—C7—N3	128.1 (2)	C6—N3—C7	107.96 (18)
N2—C7—N3	102.89 (18)	C8—N4—N3	117.27 (19)
N4—C8—C9	119.9 (2)	C13—N5—C9	117.0 (2)
N4—C8—H8	120.1	C1—S1—C4	92.36 (13)

S1—C1—C2—C3	−0.1 (3)	C6—N1—N2—C7	−1.7 (2)
C1—C2—C3—C4	0.1 (3)	N1—C6—N3—N4	−178.51 (18)
C2—C3—C4—C5	175.9 (2)	C5—C6—N3—N4	6.1 (3)
C2—C3—C4—S1	−0.1 (2)	N1—C6—N3—C7	0.3 (2)
C3—C4—C5—C6	−97.1 (3)	C5—C6—N3—C7	−175.08 (19)
S1—C4—C5—C6	78.6 (2)	O1—C7—N3—N4	−3.0 (4)
C4—C5—C6—N1	−88.2 (3)	N2—C7—N3—N4	177.40 (19)
C4—C5—C6—N3	86.5 (3)	O1—C7—N3—C6	178.4 (2)
N4—C8—C9—N5	179.39 (19)	N2—C7—N3—C6	−1.2 (2)
N4—C8—C9—C10	0.0 (3)	C9—C8—N4—N3	−179.68 (18)
N5—C9—C10—C11	−0.2 (3)	C6—N3—N4—C8	−176.92 (19)
C8—C9—C10—C11	179.1 (2)	C7—N3—N4—C8	4.6 (3)
C9—C10—C11—C12	0.2 (3)	C12—C13—N5—C9	−0.7 (3)
C10—C11—C12—C13	−0.5 (3)	C10—C9—N5—C13	0.4 (3)
C11—C12—C13—N5	0.8 (4)	C8—C9—N5—C13	−178.98 (19)
N3—C6—N1—N2	0.8 (2)	C2—C1—S1—C4	0.0 (2)
C5—C6—N1—N2	176.06 (19)	C3—C4—S1—C1	0.02 (18)
O1—C7—N2—N1	−177.8 (2)	C5—C4—S1—C1	−176.32 (19)
N3—C7—N2—N1	1.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H6···O1ⁱ	0.86	1.95	2.777 (2)	161

Symmetry code: (i) −x, −y, −z+2.

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4-(2-Pyridylmethyl­eneamino)-3-(2-thienylmeth­yl)-1H-1,2,4-triazol-5(4H)-one

Supporting information

Key indicators

checkCIF/PLATON results

4-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one