4-({(E)-[2-(But-3-en-1-yl)-1-(prop-2-en-1-yl)-4-sulfanyl-1H-imidazol-5-yl]methyl-idene}amino)-3-phenyl-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(19)H(20)N(6)S(2), the dihedral angle between the phenyl and triazole rings is 24.1 (2)° while the dihedral angles between the imidazole ring and the triazole and phenyl rings are 39.9 (2) and 55.3 (2)°, respectively. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonds which form chains along [10[Formula: see text]].

Related literature

For biological applications of Schiff base compounds, see: Liang (2003 ▶); Bacci et al. (2005 ▶). For the biological activity of triazoles and their derivatives, see: Amir et al. (2008 ▶); Sztanke et al. (2008 ▶); Padmavathi et al. (2008 ▶); Thenmozhi et al. (2010 ▶). Pharmacological compounds having triazole moieties appear to be very effective aromatese inhibitors for the prevention of breast cancer, see: Ünver et al. (2010 ▶).

Experimental

Crystal data

C19H20N6S2

M = 396.53

Monoclinic,

a = 13.384 (3) Å

b = 13.892 (3) Å

c = 11.349 (2) Å

β = 101.953 (3)°

V = 2064.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

7754 measured reflections

3788 independent reflections

3391 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.139

S = 1.07

3788 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039833/kj2187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039833/kj2187Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039833/kj2187Isup3.cml

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

C19H20N6S2	F(000) = 832
Mr = 396.53	Dx = 1.276 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 13.384 (3) Å	Cell parameters from 7754 reflections
b = 13.892 (3) Å	θ = 2.1–27.0°
c = 11.349 (2) Å	µ = 0.27 mm−1
β = 101.953 (3)°	T = 293 K
V = 2064.5 (7) Å3	Prism, pale yellow
Z = 4	0.28 × 0.25 × 0.23 mm

Bruker SMART APEX CCD area-detector diffractometer	3391 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 27.0°, θmin = 2.1°
ω scans	h = −16→16
7754 measured reflections	k = −17→17
3788 independent reflections	l = −14→13

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.8006P] where P = (Fo2 + 2Fc2)/3
3788 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
S1	0.62454 (8)	0.22573 (8)	−0.09079 (10)	0.0795 (3)
H1	0.6713	0.1935	−0.1613	0.119*
S2	0.50671 (9)	0.18382 (7)	0.24665 (11)	0.0776 (3)
N1	0.4682 (2)	0.38001 (19)	0.2489 (3)	0.0520 (6)
C2	0.4505 (3)	0.2855 (3)	0.2779 (3)	0.0607 (8)
N3	0.3797 (2)	0.2949 (2)	0.3446 (3)	0.0677 (8)
H3	0.3536	0.2465	0.3748	0.081*
N4	0.3523 (3)	0.3875 (2)	0.3605 (3)	0.0695 (8)
C5	0.4076 (3)	0.4390 (3)	0.3039 (3)	0.0565 (8)
C6	0.3977 (3)	0.5438 (3)	0.2943 (3)	0.0607 (8)
C7	0.4199 (3)	0.5949 (3)	0.1981 (4)	0.0718 (10)
H7	0.4487	0.5641	0.1405	0.086*
C8	0.3985 (4)	0.6924 (3)	0.1887 (5)	0.0930 (14)
H8	0.4135	0.7268	0.1242	0.112*
C9	0.3562 (4)	0.7392 (4)	0.2712 (6)	0.0979 (16)
H9	0.3405	0.8043	0.2621	0.117*
C10	0.3367 (5)	0.6889 (4)	0.3690 (6)	0.1026 (16)
H10	0.3098	0.7205	0.4276	0.123*
C11	0.3571 (4)	0.5923 (3)	0.3796 (5)	0.0864 (13)
H11	0.3434	0.5588	0.4454	0.104*
N12	0.5512 (2)	0.4157 (2)	0.2041 (2)	0.0534 (6)
C13	0.5707 (2)	0.3656 (2)	0.1163 (3)	0.0510 (7)
H13	0.5263	0.3157	0.0863	0.061*
C14	0.6567 (2)	0.3821 (2)	0.0621 (3)	0.0498 (7)
C15	0.6859 (3)	0.3256 (2)	−0.0233 (3)	0.0554 (8)
N16	0.7739 (2)	0.3557 (2)	−0.0521 (3)	0.0586 (7)
C17	0.8009 (3)	0.4324 (2)	0.0163 (3)	0.0576 (8)
N18	0.7337 (2)	0.45065 (18)	0.0878 (2)	0.0529 (6)
C19	0.7387 (3)	0.5317 (3)	0.1724 (3)	0.0615 (8)
H19A	0.7062	0.5130	0.2378	0.074*
H19B	0.8098	0.5459	0.2067	0.074*
C20	0.6890 (4)	0.6192 (3)	0.1151 (5)	0.0787 (12)
H20	0.6881	0.6715	0.1659	0.094*
C21	0.6481 (5)	0.6321 (4)	0.0080 (6)	0.0983 (16)
H21A	0.6465	0.5826	−0.0475	0.118*
H21B	0.6191	0.6915	−0.0170	0.118*
C22	0.8959 (4)	0.4875 (3)	0.0161 (5)	0.0925 (16)
H22A	0.9024	0.4973	−0.0666	0.111*
H22B	0.8902	0.5503	0.0514	0.111*
C23	0.9883 (4)	0.4404 (4)	0.0821 (9)	0.152 (3)
H23B	0.9879	0.3736	0.0571	0.182*
H23A	0.9880	0.4415	0.1675	0.182*
C24	1.0858 (6)	0.4886 (5)	0.0613 (15)	0.220 (6)
H24	1.0844	0.5505	0.0298	0.264*
C25	1.1675 (6)	0.4425 (8)	0.0880 (11)	0.199 (5)
H25A	1.1677	0.3807	0.1195	0.239*
H25B	1.2281	0.4700	0.0764	0.239*

	U11	U22	U33	U12	U13	U23
S1	0.0824 (7)	0.0741 (6)	0.0920 (7)	−0.0194 (5)	0.0409 (6)	−0.0316 (5)
S2	0.0906 (7)	0.0572 (5)	0.0970 (7)	−0.0004 (5)	0.0467 (6)	−0.0015 (5)
N1	0.0515 (14)	0.0552 (15)	0.0571 (15)	−0.0019 (11)	0.0294 (12)	0.0031 (12)
C2	0.0590 (19)	0.068 (2)	0.061 (2)	−0.0067 (16)	0.0263 (16)	0.0024 (15)
N3	0.0701 (18)	0.0648 (18)	0.081 (2)	−0.0029 (14)	0.0454 (16)	0.0120 (15)
N4	0.0696 (18)	0.0688 (18)	0.084 (2)	0.0036 (15)	0.0483 (17)	0.0082 (16)
C5	0.0526 (17)	0.070 (2)	0.0534 (18)	0.0031 (15)	0.0248 (14)	0.0057 (15)
C6	0.0495 (18)	0.0632 (19)	0.075 (2)	0.0059 (15)	0.0267 (16)	0.0011 (17)
C7	0.081 (2)	0.067 (2)	0.074 (2)	0.0027 (19)	0.031 (2)	0.0065 (18)
C8	0.111 (4)	0.076 (3)	0.095 (3)	0.005 (3)	0.027 (3)	0.019 (2)
C9	0.102 (4)	0.066 (3)	0.125 (4)	0.027 (2)	0.022 (3)	0.005 (3)
C10	0.112 (4)	0.082 (3)	0.127 (4)	0.024 (3)	0.057 (3)	−0.007 (3)
C11	0.092 (3)	0.087 (3)	0.095 (3)	0.023 (2)	0.053 (3)	0.002 (2)
N12	0.0522 (14)	0.0620 (15)	0.0540 (15)	−0.0017 (12)	0.0295 (12)	0.0045 (12)
C13	0.0480 (16)	0.0578 (18)	0.0504 (18)	−0.0032 (13)	0.0178 (14)	0.0021 (14)
C14	0.0515 (17)	0.0523 (16)	0.0499 (18)	0.0035 (13)	0.0208 (14)	0.0019 (13)
C15	0.0579 (18)	0.0545 (18)	0.060 (2)	0.0018 (14)	0.0274 (15)	−0.0023 (14)
N16	0.0628 (16)	0.0585 (16)	0.0652 (18)	−0.0012 (13)	0.0380 (14)	−0.0036 (13)
C17	0.063 (2)	0.0534 (17)	0.067 (2)	−0.0015 (15)	0.0368 (17)	0.0028 (15)
N18	0.0605 (15)	0.0483 (13)	0.0578 (15)	−0.0009 (12)	0.0303 (12)	0.0003 (12)
C19	0.066 (2)	0.0562 (18)	0.067 (2)	−0.0088 (15)	0.0261 (17)	−0.0108 (15)
C20	0.082 (3)	0.068 (2)	0.089 (3)	−0.002 (2)	0.024 (3)	−0.016 (2)
C21	0.108 (4)	0.073 (3)	0.106 (4)	0.014 (3)	0.006 (3)	−0.002 (3)
C22	0.095 (3)	0.082 (3)	0.125 (4)	−0.032 (3)	0.079 (3)	−0.029 (3)
C23	0.059 (3)	0.084 (3)	0.322 (11)	−0.019 (2)	0.063 (4)	−0.027 (5)
C24	0.093 (5)	0.090 (4)	0.514 (19)	−0.031 (4)	0.152 (8)	−0.058 (7)
C25	0.080 (4)	0.223 (10)	0.314 (14)	−0.025 (5)	0.087 (6)	−0.018 (10)

S1—C15	1.711 (4)	C14—C15	1.365 (4)
S1—H1	1.2000	C14—N18	1.389 (4)
S2—C2	1.673 (4)	C15—N16	1.352 (4)
N1—C2	1.385 (5)	N16—C17	1.324 (5)
N1—C5	1.389 (4)	C17—N18	1.355 (4)
N1—N12	1.405 (4)	C17—C22	1.485 (5)
C2—N3	1.337 (5)	N18—C19	1.472 (4)
N3—N4	1.359 (4)	C19—C20	1.471 (6)
N3—H3	0.8600	C19—H19A	0.9700
N4—C5	1.292 (4)	C19—H19B	0.9700
C5—C6	1.463 (5)	C20—C21	1.239 (7)
C6—C11	1.380 (5)	C20—H20	0.9300
C6—C7	1.386 (5)	C21—H21A	0.9300
C7—C8	1.384 (6)	C21—H21B	0.9300
C7—H7	0.9300	C22—C23	1.461 (9)
C8—C9	1.356 (8)	C22—H22A	0.9700
C8—H8	0.9300	C22—H22B	0.9700
C9—C10	1.381 (8)	C23—C24	1.529 (8)
C9—H9	0.9300	C23—H23B	0.9700
C10—C11	1.370 (7)	C23—H23A	0.9700
C10—H10	0.9300	C24—C25	1.250 (13)
C11—H11	0.9300	C24—H24	0.9300
N12—C13	1.285 (4)	C25—H25A	0.9300
C13—C14	1.432 (4)	C25—H25B	0.9300
C13—H13	0.9300
C15—S1—H1	109.5	N16—C15—S1	120.2 (2)
C2—N1—C5	107.9 (3)	C14—C15—S1	127.1 (3)
C2—N1—N12	127.4 (3)	C17—N16—C15	104.6 (3)
C5—N1—N12	122.3 (3)	N16—C17—N18	111.6 (3)
N3—C2—N1	102.6 (3)	N16—C17—C22	123.0 (3)
N3—C2—S2	127.2 (3)	N18—C17—C22	125.4 (3)
N1—C2—S2	130.1 (3)	C17—N18—C14	107.5 (3)
C2—N3—N4	114.2 (3)	C17—N18—C19	126.0 (3)
C2—N3—H3	122.9	C14—N18—C19	126.4 (3)
N4—N3—H3	122.9	C20—C19—N18	112.8 (3)
C5—N4—N3	105.1 (3)	C20—C19—H19A	109.0
N4—C5—N1	110.2 (3)	N18—C19—H19A	109.0
N4—C5—C6	122.4 (3)	C20—C19—H19B	109.0
N1—C5—C6	127.2 (3)	N18—C19—H19B	109.0
C11—C6—C7	118.8 (4)	H19A—C19—H19B	107.8
C11—C6—C5	118.4 (4)	C21—C20—C19	128.4 (4)
C7—C6—C5	122.6 (3)	C21—C20—H20	115.8
C8—C7—C6	119.2 (4)	C19—C20—H20	115.8
C8—C7—H7	120.4	C20—C21—H21A	120.0
C6—C7—H7	120.4	C20—C21—H21B	120.0
C9—C8—C7	121.6 (5)	H21A—C21—H21B	120.0
C9—C8—H8	119.2	C23—C22—C17	113.7 (4)
C7—C8—H8	119.2	C23—C22—H22A	108.8
C8—C9—C10	119.2 (4)	C17—C22—H22A	108.8
C8—C9—H9	120.4	C23—C22—H22B	108.8
C10—C9—H9	120.4	C17—C22—H22B	108.8
C11—C10—C9	119.9 (5)	H22A—C22—H22B	107.7
C11—C10—H10	120.1	C22—C23—C24	112.6 (7)
C9—C10—H10	120.1	C22—C23—H23B	109.1
C10—C11—C6	121.2 (5)	C24—C23—H23B	109.1
C10—C11—H11	119.4	C22—C23—H23A	109.1
C6—C11—H11	119.4	C24—C23—H23A	109.1
C13—N12—N1	113.1 (3)	H23B—C23—H23A	107.8
N12—C13—C14	123.8 (3)	C25—C24—C23	118.0 (9)
N12—C13—H13	118.1	C25—C24—H24	121.0
N14—C13—H13	118.1	C23—C24—H24	121.0
C15—C14—N18	103.6 (3)	C24—C25—H25A	120.0
C15—C14—C13	125.9 (3)	C24—C25—H25B	120.0
N18—C14—C13	130.3 (3)	H25A—C25—H25B	120.0
N16—C15—C14	112.7 (3)
C5—N1—C2—N3	1.5 (4)	N1—N12—C13—C14	−174.4 (3)
N12—N1—C2—N3	164.0 (3)	N12—C13—C14—C15	173.5 (3)
C5—N1—C2—S2	−175.1 (3)	N12—C13—C14—N18	−0.4 (5)
N12—N1—C2—S2	−12.6 (6)	N18—C14—C15—N16	−0.8 (4)
N1—C2—N3—N4	−0.5 (4)	C13—C14—C15—N16	−176.0 (3)
S2—C2—N3—N4	176.2 (3)	N18—C14—C15—S1	178.4 (3)
C2—N3—N4—C5	−0.7 (4)	C13—C14—C15—S1	3.3 (5)
N3—N4—C5—N1	1.6 (4)	C14—C15—N16—C17	0.1 (4)
N3—N4—C5—C6	177.0 (3)	S1—C15—N16—C17	−179.2 (3)
C2—N1—C5—N4	−2.0 (4)	C15—N16—C17—N18	0.7 (4)
N12—N1—C5—N4	−165.6 (3)	C15—N16—C17—C22	178.4 (4)
C2—N1—C5—C6	−177.2 (4)	N16—C17—N18—C14	−1.3 (4)
N12—N1—C5—C6	19.2 (5)	C22—C17—N18—C14	−178.8 (4)
N4—C5—C6—C11	23.2 (6)	N16—C17—N18—C19	−178.2 (3)
N1—C5—C6—C11	−162.2 (4)	C22—C17—N18—C19	4.2 (6)
N4—C5—C6—C7	−151.5 (4)	C15—C14—N18—C17	1.2 (3)
N1—C5—C6—C7	23.0 (6)	C13—C14—N18—C17	176.1 (3)
C11—C6—C7—C8	−1.5 (6)	C15—C14—N18—C19	178.1 (3)
C5—C6—C7—C8	173.2 (4)	C13—C14—N18—C19	−7.0 (5)
C6—C7—C8—C9	−0.1 (8)	C17—N18—C19—C20	86.8 (4)
C7—C8—C9—C10	1.9 (9)	C14—N18—C19—C20	−89.6 (4)
C8—C9—C10—C11	−2.1 (9)	N18—C19—C20—C21	−2.4 (7)
C9—C10—C11—C6	0.4 (9)	N16—C17—C22—C23	−76.5 (6)
C7—C6—C11—C10	1.4 (7)	N18—C17—C22—C23	100.8 (5)
C5—C6—C11—C10	−173.5 (5)	C17—C22—C23—C24	169.4 (7)
C2—N1—N12—C13	47.3 (4)	C22—C23—C24—C25	−162.9 (12)
C5—N1—N12—C13	−152.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N16i	0.86	2.05	2.907 (5)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N16i	0.86	2.05	2.907 (5)	172

Symmetry code: (i) .