4-Allyl-3-(2-methyl-4-quinol-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(15)H(14)N(4)S, the quinoline and triazole rings form a dihedral angle of 41.48 (7)°. In the crystal, adjacent mol-ecules 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 = 282.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.171

S = 1.09

2897 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.60 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044697/ng5047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14N4S	F(000) = 592
Mr = 282.37	Dx = 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

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: Fine–focus sealed tube	θmax = 74.9°, θmin = 4.8°
Graphite	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 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(Fo2) + (0.0953P)2 + 0.6742P] where P = (Fo2 + 2Fc2)/3
2897 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .