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

Natarajan, S.; Mathews, R.

doi:10.1107/S1600536811039833

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2828

doi:10.1107/S1600536811039833

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

Sampath Natarajan ^a ^* and Rita Mathews ^a

^aDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143 701, Republic of Korea
^*Correspondence e-mail: sampath@konkuk.ac.kr, sams76@gmail.com

(Received 19 August 2011; accepted 28 September 2011; online 5 October 2011)

In the title compound, C₁₉H₂₀N₆S₂, 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 intermolecular N—H⋯N hydrogen bonds which form chains along [10 $[\overline{1}]$ ].

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_r = 396.53
Monoclinic, C c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.139
S = 1.07
3788 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811039833/kj2187sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811039833/kj2187Isup3.cml

checkCIF report

Comment top

Synthesis and structural investigation of Schiff base compounds have been given attention due to their interesting structural features and potential biological applications (Liang, 2003; Bacci et al., 2005). The biological importance of imidazoles and triazoles has stimulated much work on these heterocycles. Triazole compounds and their derivatives have many applications in medicine and were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti-inflammatory, anticancer and antioxidant properties (Amir et al., 2008; Sztanke et al., 2008; Padmavathi et al., 2008; Thenmozhi et al., 2010). The 1,2,4-triazole group interacts strongly with heme iron and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, it was reported that pharmacological compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatese inhibitors for preventing breast cancer (Ünver et al., 2010). In view of these important applications of imidazolines, here we report the crystal structure of the title compound (Fig. 1).

The title compound contains imidazole and 1,2,4-triazole rings connected by an imine group. A phenyl ring is substituted at position 5 of the triazole ring and the dihedral angle between these rings is 24.1 (2)°. The imidazole and triazole groups are substituted on the imine group (N12—C13) in the E-configuration [N1—N12—C13—C14 = -174.4 (3)°]. The triazole ring is not co-planar with the imidazole ring and this may be due to the substitution of the phenyl ring on the triazole ring. The dihedral angles between the imidazole ring and the triazole and phenyl rings are 39.9 (2)° and 55.3 (2)°, respectively. The imidazole ring is substituted by bulky groups (3-butene, 2-propene) as well as an imine and a thiol group, which gives strain on the ring. The 3-butene and imine substituents show an extended zigzag confirmation with respect to the imidazole ring.

The packing diagram of the title compound viewed down the a axis is shown in Fig. 2. The crystal packing displays intermolecular N—H···N hydrogen bonds (Table 1), which join the molecules into chains in the [1 0 -1] direction.

Related literature top

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 top

The title compound was synthesized by refluxing 4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.01 mmol) and 2-(but-3-en-1-yl)-1-(prop-2-en-1-yl)-4-sulfanyl-1H-imidazole-5- carbaldehyde (0.01 mmol) in ethanol (50 ml) with a few drops of H₂SO₄ for 3 h on a water bath. The reaction progress was monitored by TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 74% yield. The resulting Schiff base compound was seperated out and crystallized in ethanol.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. ORTEP diagram of the title molecule with the atom numbering scheme. H atoms were omitted. Displacement ellipsoid are drawn at 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. H atoms not involved in hydrogen bonds were omitted. Dashed lines indicate the intermolecular interactions between the molecules.

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

Crystal data top

C₁₉H₂₀N₆S₂	F(000) = 832
M_r = 396.53	D_x = 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

Data collection top

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

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0788P)² + 0.8006P] where P = (F_o² + 2F_c²)/3
3788 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.33 e Å⁻³
2 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₂₀N₆S₂	V = 2064.5 (7) Å³
M_r = 396.53	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 13.384 (3) Å	µ = 0.27 mm⁻¹
b = 13.892 (3) Å	T = 293 K
c = 11.349 (2) Å	0.28 × 0.25 × 0.23 mm
β = 101.953 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3391 reflections with I > 2σ(I)
7754 measured reflections	R_int = 0.017
3788 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	2 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
3788 reflections	Δρ_min = −0.21 e Å⁻³
244 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₆S₂
M_r	396.53
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	13.384 (3), 13.892 (3), 11.349 (2)
β (°)	101.953 (3)
V (Å³)	2064.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.28 × 0.25 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7754, 3788, 3391
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.139, 1.07
No. of reflections	3788
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2.

References

Amir, M., Kumar, H. & Javed, S. A. (2008). Eur. J. Med. Chem. 43, 2056–2066. Web of Science CrossRef PubMed CAS Google Scholar
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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Liang, F.-Z. (2003). J. Shandong Normal Univ. (Nat. Sci.), 18, 50–51. Google Scholar
Padmavathi, V., Thriveni, P., Reddy, G. S. & Deepti, D. (2008). Eur. J. Med. Chem. 43, 917–924. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sztanke, K., Tuzimski, T., Rzymowska, J., Pasternak, K. & Kandefer-Szerszen, M. (2008). Eur. J. Med. Chem. 43, 404–419. Web of Science CrossRef PubMed CAS Google Scholar
Thenmozhi, M., Kavitha, T., Reddy, B. P., Vijayakumar, V. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o558. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ünver, Y., Köysal, Y., Tanak, H., Ünlüer, D. & Işık, Ş. (2010). Acta Cryst. E66, o1294. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o2828

doi:10.1107/S1600536811039833

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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