4-Allyl-3-(2-methyl-4-quinol­yl)-1H-1,2,4-triazole-5(4H)-thione

Kashaev, A.G.; Zimichev, A.V.; Rybakov, V.B.; Klimochkin, Y.N.; Zemtsova, M.N.

doi:10.1107/S1600536810044697

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3090

https://doi.org/10.1107/S1600536810044697

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4-Allyl-3-(2-methyl-4-quinolyl)-1H-1,2,4-triazole-5(4H)-thione

Artyom G. Kashaev,^a Anatoliy V. Zimichev,^a Victor B. Rybakov,^b ^* Yurij N. Klimochkin ^a and Margarita N. Zemtsova ^a

^aSamara State Technical University, Molodogvardeyskay Str. 244, 443100 Samara, Russian Federation, and ^bDepartment of Chemistry, Moscow State University, 119992 Moscow, Russian Federation
^*Correspondence e-mail: rybakov20021@yandex.ru

(Received 13 October 2010; accepted 1 November 2010; online 6 November 2010)

In the title compound, C₁₅H₁₄N₄S, the quinoline and triazole rings form a dihedral angle of 41.48 (7)°. In the crystal, adjacent molecules are linked by N—H⋯N hydrogen bonds, forming chains along [100].

Related literature

For the use of hydrazides and their functional derivatives in the preparation of a series of antitubercular and antibacterial compounds, see: Anghel & Silberg (1971 ); Figueiredo et al. (2000 ).

Experimental

Crystal data

C₁₅H₁₄N₄S
M_r = 282.37
Monoclinic, P 2₁ /n
a = 7.8184 (8) Å
b = 11.5159 (13) Å
c = 15.7723 (14) Å
β = 96.034 (9)°
V = 1412.2 (3) Å³
Z = 4
Cu Kα radiation
μ = 1.99 mm⁻¹
T = 295 K
0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
2897 measured reflections
2897 independent reflections
2570 reflections with I > 2σ(I)
1 standard reflections every 60 min intensity decay: 4%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.171
S = 1.09
2897 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14⋯N1ⁱ	0.86	2.21	2.978 (3)	148
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044697/ng5047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044697/ng5047Isup2.hkl

checkCIF report

Comment top

Hydrazides and their functional derivatives were used to prepare a series of antitubercular and antibacterial compounds (Anghel & Silberg, 1971; Figueiredo et al., 2000). Many heterocyclic compounds directly prepared from hydrazides, too, possess valuable biological and physicochemical properties. This causes an attention to new synthetic methods and investigation of similar compounds. N–(Allylthiocarbonyl)–4–(2–methyl–4–quinolyl)–carbohydrazide, I, was synthesized from allyl isothiocyanate and hydrazide 2–methyl–4–quinoline carboxylic acid. When heated with alkali for 1 h, the product undergoes cyclization into 4-allyl-3-(2-methyl-4-quinolyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione, II (Fig. 1).

In title molecule, guinoline moiety is planar (max deviation of C6 = 0.039 (2) Å) and assential planar triazole moiety form dihedral angle 41.48 (7)° (Fig. 2). In the crystal structure is found classical hydrogen bond N14—H14···N1ⁱ with parameters N14—H14 = 0.86 Å, N14···N1ⁱ = 2.978 (3) Å, H14···N1ⁱ = 2.21Å and angle N14—H14···N1ⁱ = 147.8°. Non–classical H bond is found too: C21—H21A···N15ⁱⁱ with parameters C21—H21A = 0.96 Å, C21···N15ⁱⁱ = 3.330 (3) Å, H21A···N15ⁱⁱ = 2.450Å and angle C21—H21A···N15ⁱⁱ = 152°. Is found σ···π–interaction between H8—>C17ⁱⁱⁱ═C18ⁱⁱⁱ (H8···C17ⁱⁱⁱ = 2.800Å and H8···C18ⁱⁱⁱ = 2.896 Å). Symmetry codes: (i) x + 1/2, -y + 3/2, z + 1/2; (ii) x - 1/2, -y + 3/2, z - 1/2; (iii) x, y - 1, z.

Related literature top

For the use of hydrazides and their functional derivatives in the preparation of a series of

antitubercular and antibacterial compounds, see: Anghel & Silberg (1971); Figueiredo et al. (2000).

Experimental top

A solution of 1.43 mmol of NaOH in 10 ml of water was added to 0.95 mmol of N–(allylthiocarbonyl)–4–(2–methyl–4–quinolyl)–carbohydrazide, and the mixture was refluxed for 1 h. The solution was cooled and acidified with acetic acid to pH 4. The precipitate that formed was filtered off and recrystallized from ethanol. Recrystallization of the crude product from ethanol gave 0.2 g of colourless crystals. Yield 73%, m.p. 494–495 K.

IR, ν, cm^-1: 3432 (NH), 3324 (NH), 1348 (C═S). MS, m/z: 282 (100) [M]+, 245 (39), 267 (62), 169 (66), 168 (61), 140 (23). ¹H NMR, δ: 2.68 s (3H, CH₃), 3.92 s (1H, NH), 4.53 d (2H, J = 5.04, —CH₂—CH═CH₂), 4.67 d (1H, J = 10.53, —CH═CH₂ trans), 5.17 dd (1H, J = 16.94, —CH═CH₂ cis), 5.62 m (1H, —CH═), 7.55 t (1H, J = 7.34, 7–H), 7.66 s (1H, 3–H), 7.76 t (1H, J = 7.74, 6–H), 7.78 d (1H, J = 8.24, 8–H), 8.00 d (1H, J = 8.70, 5–H). Anal. calc. for C₁₅H₁₄N₄S, %: C 63.80; H 5.00; N 19.84; S 11.36. Found, %: C 63.68; H 5.09; N 11.44; S 11.31.

Single crystals for X–ray analysis were obtained by slow evaporation of an ethanol. IR spectrum was recorded (in KBr) on Shimadzu FTIR–8400S. Mass spectrum was measured on Finnigan Trance DSQ spectrometer. ¹H NMR spectrum was obtained in DMSO–d₆ on Bruker AM 300 (300 MHz), using TMS as internal standard. Elemental composition was determined on Euro Vector EA–3000 elemental analyzer.

Structure description top

For the use of hydrazides and their functional derivatives in the preparation of a series of

antitubercular and antibacterial compounds, see: Anghel & Silberg (1971); Figueiredo et al. (2000).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Synthesis of the title compound.
	Fig. 2. ORTEP–3 (Farrugia, 1997) plot of molecular structure of the title compound showing the atom–numbering scheme. Thermal displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

4-Allyl-3-(2-methyl-4-quinolyl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₅H₁₄N₄S	F(000) = 592
M_r = 282.37	D_x = 1.328 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 494–495 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 7.8184 (8) Å	Cell parameters from 25 reflections
b = 11.5159 (13) Å	θ = 29.9–32.4°
c = 15.7723 (14) Å	µ = 1.99 mm⁻¹
β = 96.034 (9)°	T = 295 K
V = 1412.2 (3) Å³	Prism, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: Fine–focus sealed tube	θ_max = 74.9°, θ_min = 4.8°
Graphite monochromator	h = −9→9
non–profiled ω scans	k = 0→14
2897 measured reflections	l = 0→19
2897 independent reflections	1 standard reflections every 60 min
2570 reflections with I > 2σ(I)	intensity decay: 4%

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0953P)² + 0.6742P] where P = (F_o² + 2F_c²)/3
2897 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₅H₁₄N₄S	V = 1412.2 (3) Å³
M_r = 282.37	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.8184 (8) Å	µ = 1.99 mm⁻¹
b = 11.5159 (13) Å	T = 295 K
c = 15.7723 (14) Å	0.20 × 0.20 × 0.20 mm
β = 96.034 (9)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
2897 measured reflections	1 standard reflections every 60 min
2897 independent reflections	intensity decay: 4%
2570 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
2897 reflections	Δρ_min = −0.60 e Å⁻³
182 parameters

Special details top

Geometry. All s.u.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F², conventional R–factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R–factors(gt) 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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	−0.0256 (3)	0.68265 (17)	0.64417 (12)	0.0489 (4)
C2	0.0117 (3)	0.7945 (2)	0.64169 (14)	0.0510 (5)
C21	−0.0078 (5)	0.8565 (2)	0.55821 (17)	0.0707 (8)
H21A	−0.0327	0.8014	0.5129	0.106*
H21B	0.0971	0.8967	0.5505	0.106*
H21C	−0.1002	0.9115	0.5575	0.106*
C3	0.0741 (3)	0.8566 (2)	0.71541 (14)	0.0504 (5)
H3	0.1053	0.9340	0.7105	0.060*
C4	0.0898 (3)	0.80569 (19)	0.79389 (13)	0.0450 (5)
C5	0.0448 (3)	0.6859 (2)	0.79967 (13)	0.0452 (5)
C6	0.0506 (4)	0.6230 (2)	0.87675 (16)	0.0572 (6)
H6	0.0809	0.6605	0.9284	0.069*
C7	0.0115 (4)	0.5067 (2)	0.87563 (18)	0.0677 (7)
H7	0.0161	0.4656	0.9266	0.081*
C8	−0.0351 (4)	0.4498 (2)	0.79841 (18)	0.0636 (7)
H8	−0.0601	0.3708	0.7986	0.076*
C9	−0.0446 (3)	0.5078 (2)	0.72313 (15)	0.0521 (5)
H9	−0.0757	0.4685	0.6723	0.063*
C10	−0.0073 (3)	0.62756 (19)	0.72191 (14)	0.0445 (5)
C11	0.1589 (3)	0.87239 (19)	0.86904 (13)	0.0438 (5)
N12	0.1212 (2)	0.98612 (16)	0.88595 (11)	0.0426 (4)
C13	0.2140 (3)	1.0161 (2)	0.96191 (13)	0.0461 (5)
S13	0.20807 (9)	1.14068 (5)	1.01518 (4)	0.0584 (2)
N14	0.3062 (3)	0.91993 (18)	0.98323 (11)	0.0509 (5)
H14	0.3792	0.9153	1.0279	0.061*
N15	0.2733 (3)	0.83085 (18)	0.92762 (12)	0.0512 (5)
C16	−0.0166 (3)	1.0582 (2)	0.84356 (15)	0.0479 (5)
H16A	−0.0686	1.1025	0.8864	0.057*
H16B	−0.1045	1.0080	0.8154	0.057*
C17	0.0426 (3)	1.1402 (2)	0.77948 (17)	0.0544 (6)
H17	0.1430	1.1819	0.7946	0.065*
C18	−0.0369 (4)	1.1571 (3)	0.70368 (19)	0.0670 (7)
H18A	−0.1377	1.1167	0.6865	0.080*
H18B	0.0070	1.2096	0.6667	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0549 (11)	0.0500 (10)	0.0402 (9)	0.0018 (8)	−0.0018 (8)	−0.0032 (8)
C2	0.0626 (14)	0.0476 (12)	0.0413 (11)	0.0030 (10)	−0.0012 (9)	−0.0011 (9)
C21	0.109 (2)	0.0540 (15)	0.0459 (13)	−0.0009 (14)	−0.0077 (14)	0.0031 (11)
C3	0.0633 (14)	0.0436 (12)	0.0431 (12)	0.0006 (10)	−0.0004 (10)	−0.0017 (9)
C4	0.0485 (11)	0.0460 (11)	0.0398 (11)	0.0019 (9)	0.0016 (8)	−0.0034 (9)
C5	0.0489 (11)	0.0448 (11)	0.0413 (11)	0.0035 (9)	0.0025 (8)	−0.0019 (9)
C6	0.0772 (17)	0.0522 (13)	0.0417 (12)	−0.0016 (12)	0.0037 (11)	0.0006 (10)
C7	0.099 (2)	0.0514 (14)	0.0521 (14)	−0.0034 (14)	0.0051 (13)	0.0072 (11)
C8	0.0819 (19)	0.0430 (12)	0.0656 (16)	−0.0012 (12)	0.0059 (13)	−0.0003 (11)
C9	0.0570 (13)	0.0467 (12)	0.0517 (13)	0.0013 (10)	0.0017 (10)	−0.0068 (10)
C10	0.0457 (11)	0.0454 (11)	0.0421 (11)	0.0032 (9)	0.0027 (8)	−0.0024 (8)
C11	0.0487 (11)	0.0439 (11)	0.0384 (10)	0.0003 (9)	0.0022 (8)	−0.0025 (8)
N12	0.0456 (9)	0.0429 (9)	0.0392 (9)	−0.0006 (7)	0.0045 (7)	−0.0013 (7)
C13	0.0497 (11)	0.0497 (12)	0.0394 (10)	−0.0056 (9)	0.0070 (8)	−0.0023 (9)
S13	0.0753 (5)	0.0485 (4)	0.0524 (4)	−0.0073 (3)	0.0107 (3)	−0.0104 (2)
N14	0.0568 (11)	0.0537 (11)	0.0402 (9)	0.0034 (9)	−0.0039 (8)	−0.0066 (8)
N15	0.0582 (11)	0.0496 (10)	0.0436 (10)	0.0068 (9)	−0.0044 (8)	−0.0062 (8)
C16	0.0475 (11)	0.0469 (12)	0.0498 (12)	0.0049 (9)	0.0071 (9)	0.0032 (9)
C17	0.0574 (13)	0.0440 (12)	0.0626 (14)	−0.0004 (10)	0.0106 (11)	0.0053 (10)
C18	0.0805 (19)	0.0596 (15)	0.0617 (16)	0.0015 (13)	0.0115 (13)	0.0118 (12)

Geometric parameters (Å, º) top

N1—C2	1.322 (3)	C8—H8	0.9300
N1—C10	1.375 (3)	C9—C10	1.411 (3)
C2—C3	1.408 (3)	C9—H9	0.9300
C2—C21	1.492 (3)	C11—N15	1.307 (3)
C21—H21A	0.9600	C11—N12	1.375 (3)
C21—H21B	0.9600	N12—C13	1.377 (3)
C21—H21C	0.9600	N12—C16	1.465 (3)
C3—C4	1.363 (3)	C13—N14	1.345 (3)
C3—H3	0.9300	C13—S13	1.666 (2)
C4—C5	1.430 (3)	N14—N15	1.357 (3)
C4—C11	1.467 (3)	N14—H14	0.8600
C5—C6	1.411 (3)	C16—C17	1.491 (3)
C5—C10	1.420 (3)	C16—H16A	0.9700
C6—C7	1.374 (4)	C16—H16B	0.9700
C6—H6	0.9300	C17—C18	1.303 (4)
C7—C8	1.397 (4)	C17—H17	0.9300
C7—H7	0.9300	C18—H18A	0.9300
C8—C9	1.357 (4)	C18—H18B	0.9300

C2—N1—C10	118.25 (19)	C10—C9—H9	120.0
N1—C2—C3	121.9 (2)	N1—C10—C9	117.5 (2)
N1—C2—C21	119.4 (2)	N1—C10—C5	123.1 (2)
C3—C2—C21	118.7 (2)	C9—C10—C5	119.4 (2)
C2—C21—H21A	109.5	N15—C11—N12	110.86 (19)
C2—C21—H21B	109.5	N15—C11—C4	123.1 (2)
H21A—C21—H21B	109.5	N12—C11—C4	125.98 (19)
C2—C21—H21C	109.5	C11—N12—C13	107.68 (18)
H21A—C21—H21C	109.5	C11—N12—C16	127.87 (18)
H21B—C21—H21C	109.5	C13—N12—C16	123.32 (19)
C4—C3—C2	121.5 (2)	N14—C13—N12	103.32 (19)
C4—C3—H3	119.3	N14—C13—S13	128.73 (17)
C2—C3—H3	119.3	N12—C13—S13	127.93 (18)
C3—C4—C5	118.3 (2)	C13—N14—N15	113.62 (18)
C3—C4—C11	119.9 (2)	C13—N14—H14	123.2
C5—C4—C11	121.75 (19)	N15—N14—H14	123.2
C6—C5—C10	118.8 (2)	C11—N15—N14	104.45 (19)
C6—C5—C4	124.3 (2)	N12—C16—C17	113.73 (19)
C10—C5—C4	116.8 (2)	N12—C16—H16A	108.8
C7—C6—C5	120.1 (2)	C17—C16—H16A	108.8
C7—C6—H6	119.9	N12—C16—H16B	108.8
C5—C6—H6	119.9	C17—C16—H16B	108.8
C6—C7—C8	120.4 (2)	H16A—C16—H16B	107.7
C6—C7—H7	119.8	C18—C17—C16	124.4 (3)
C8—C7—H7	119.8	C18—C17—H17	117.8
C9—C8—C7	121.1 (2)	C16—C17—H17	117.8
C9—C8—H8	119.4	C17—C18—H18A	120.0
C7—C8—H8	119.4	C17—C18—H18B	120.0
C8—C9—C10	120.0 (2)	H18A—C18—H18B	120.0
C8—C9—H9	120.0

C10—N1—C2—C3	2.0 (4)	C4—C5—C10—C9	176.7 (2)
C10—N1—C2—C21	−179.7 (2)	C3—C4—C11—N15	−135.3 (3)
N1—C2—C3—C4	−3.8 (4)	C5—C4—C11—N15	41.9 (3)
C21—C2—C3—C4	178.0 (3)	C3—C4—C11—N12	41.3 (3)
C2—C3—C4—C5	1.4 (4)	C5—C4—C11—N12	−141.6 (2)
C2—C3—C4—C11	178.6 (2)	N15—C11—N12—C13	−2.3 (3)
C3—C4—C5—C6	−178.3 (2)	C4—C11—N12—C13	−179.2 (2)
C11—C4—C5—C6	4.5 (4)	N15—C11—N12—C16	−170.3 (2)
C3—C4—C5—C10	2.3 (3)	C4—C11—N12—C16	12.7 (4)
C11—C4—C5—C10	−174.9 (2)	C11—N12—C13—N14	2.6 (2)
C10—C5—C6—C7	2.0 (4)	C16—N12—C13—N14	171.29 (19)
C4—C5—C6—C7	−177.3 (3)	C11—N12—C13—S13	−175.96 (17)
C5—C6—C7—C8	−0.3 (5)	C16—N12—C13—S13	−7.2 (3)
C6—C7—C8—C9	−0.7 (5)	N12—C13—N14—N15	−2.2 (3)
C7—C8—C9—C10	−0.1 (4)	S13—C13—N14—N15	176.36 (17)
C2—N1—C10—C9	−178.8 (2)	N12—C11—N15—N14	0.9 (3)
C2—N1—C10—C5	2.0 (3)	C4—C11—N15—N14	178.0 (2)
C8—C9—C10—N1	−177.5 (2)	C13—N14—N15—C11	0.8 (3)
C8—C9—C10—C5	1.8 (4)	C11—N12—C16—C17	−100.9 (3)
C6—C5—C10—N1	176.5 (2)	C13—N12—C16—C17	92.8 (3)
C4—C5—C10—N1	−4.1 (3)	N12—C16—C17—C18	134.9 (3)
C6—C5—C10—C9	−2.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···N1ⁱ	0.86	2.21	2.978 (3)	148

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄S
M_r	282.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.8184 (8), 11.5159 (13), 15.7723 (14)
β (°)	96.034 (9)
V (Å³)	1412.2 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2897, 2897, 2570
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.171, 1.09
No. of reflections	2897
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.60

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···N1ⁱ	0.86	2.21	2.978 (3)	147.8

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

Acknowledgements

The authors are indebted to Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database.

References

Anghel, C. & Silberg, A. (1971). Studia Univ. Babes–Bolyai Chem. 16, 9–12. CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Figueiredo, J. M., Camara, C. de A., Amarante, E. G., Miranda, A. L. P., Santos, F. M., Rodrigues, C. R., Fraga, C. A. M. & Barreiro, E. J. (2000). Bioorg. Med. Chem. 8, 2243–2248. Web of Science CrossRef PubMed CAS Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar