4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl­idene]amino}-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Hemamalini, M.; Malladi, S.; Isloor, A.M.

doi:10.1107/S1600536811024834

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1944

doi:10.1107/S1600536811024834

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4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]amino}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Shridhar Malladi ^b and Arun M. Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology, Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 June 2011; accepted 24 June 2011; online 9 July 2011)

In the title compound, C₁₂H₁₀N₆S, a weak intramolecular C—H⋯S hydrogen bond stabilizes the molecular conformation. The pyrazole and triazole rings form a dihedral angle of 17.82 (8)°. The molecule adopts an E configuration with respect to the central C=N double bond. In the crystal, intermolecular N—H⋯N and N—H⋯S hydrogen bonds link molecules into chains propagating in [20 $[\overline{1}]$ ].

Related literature

For applications of Schiff bases, see: Kahveci et al. (2005 ); Bekircan et al. (2006 ); Singh & Dash (1988 ). For a related structure, see: Fun et al. (2010 ).

Experimental

Crystal data

C₁₂H₁₀N₆S
M_r = 270.32
Monoclinic, P 2₁ /c
a = 4.1180 (4) Å
b = 17.9237 (16) Å
c = 17.0787 (15) Å
β = 97.352 (3)°
V = 1250.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.55 × 0.26 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.872, T_max = 0.954
14262 measured reflections
4361 independent reflections
3204 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.03
4361 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.84 (2)	2.59 (2)	3.3593 (15)	153.6 (17)
N6—H1N6⋯N1ⁱⁱ	0.90 (2)	1.91 (2)	2.7884 (15)	168.0 (2)
C10—H10A⋯S1	0.93	2.50	3.2183 (13)	134
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024834/cv5118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024834/cv5118Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024834/cv5118Isup3.cml

checkCIF report

Comment top

Schiff bases derived from various heterocycles have been reported to possess antimicrobial (Kahveci et al., 2005), anticancer (Bekircan et al., 2006) and antifungal (Singh et al., 1988) activities. Recently, we have reported the crystal structure of 3-Ethyl-6-[3-(4-fluorophenyl)-1H-pyrazole-4-yl]- 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (Fun et al., 2010). In continuation of our studies of triazole derivatives, the title compound, (I), has been synthesized. Herewith we present its crystal structure.

In (I) (Fig. 1), the central pyrazole ring (N1–N2/C7–C9) makes dihedral angles of 37.64 (8) and 17.82 (8)° with the adjacent phenyl (C1–C6) and triazole (N4–N6/C11–C12) rings, respectively. The dihedral angle between the terminal phenyl (C1–C6) and triazole (N4–N6/C11–C12) rings is 47.08 (9)°. The molecule adopts an E configuration about the central C10═N3 double bond.

In the crystal structure, intermolecular N6—H1N6···N1 and N2—H1N2···S1 (Table 1) hydrogen bonds link the molecules into chains propagated in [2 0 -1].

Related literature top

For applications of Schiff bases, see: Kahveci et al. (2005); Bekircan et al. (2006); Singh & Dash (1988). For a related structure, see: Fun et al. (2010).

Experimental top

An equimolar mixture of 4-amino-4H-1,2,4-triazole-3-thiol (0.116 g, 0.001 mol) and 3-phenyl-1H-pyrazole-4-carbaldehyde (0.172 g, 0.001) in ethanol were refluxed for 7–8 hours in presence of catalytic amount of sulfuric acid. The precipitated solid was filtered, washed with ethanol and recrystallised from ethanol-dioxane mixture. Yield: 0.214 g, 79.25%. M.p- 526–528 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed line denotes weak intramolecular hydrogen bond.

4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]amino}- 1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₂H₁₀N₆S	F(000) = 560
M_r = 270.32	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4488 reflections
a = 4.1180 (4) Å	θ = 2.7–32.1°
b = 17.9237 (16) Å	µ = 0.25 mm⁻¹
c = 17.0787 (15) Å	T = 296 K
β = 97.352 (3)°	Block, colourless
V = 1250.2 (2) Å³	0.55 × 0.26 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4361 independent reflections
Radiation source: fine-focus sealed tube	3204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 32.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→6
T_min = 0.872, T_max = 0.954	k = −23→26
14262 measured reflections	l = −24→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0574P)² + 0.2417P] where P = (F_o² + 2F_c²)/3
4361 reflections	(Δ/σ)_max = 0.001
180 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₂H₁₀N₆S	V = 1250.2 (2) Å³
M_r = 270.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.1180 (4) Å	µ = 0.25 mm⁻¹
b = 17.9237 (16) Å	T = 296 K
c = 17.0787 (15) Å	0.55 × 0.26 × 0.19 mm
β = 97.352 (3)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4361 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3204 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.954	R_int = 0.022
14262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.29 e Å⁻³
4361 reflections	Δρ_min = −0.28 e Å⁻³
180 parameters

Special details top

Geometry. All s.u.'s (except the s.u. 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
S1	0.40558 (10)	0.78578 (2)	0.54047 (2)	0.04665 (12)
N1	0.9965 (3)	0.79730 (6)	0.20882 (6)	0.0407 (3)
N2	1.0317 (3)	0.72254 (7)	0.20392 (7)	0.0420 (3)
N3	0.5720 (3)	0.66043 (6)	0.39821 (6)	0.0384 (2)
N4	0.3925 (3)	0.64999 (5)	0.46129 (6)	0.0348 (2)
N5	0.1337 (4)	0.57751 (7)	0.53767 (7)	0.0488 (3)
N6	0.1665 (3)	0.64885 (6)	0.56639 (7)	0.0413 (3)
C1	0.6630 (4)	0.93695 (8)	0.23797 (9)	0.0472 (3)
H1A	0.6471	0.9232	0.1851	0.057*
C2	0.5789 (5)	1.00854 (9)	0.25766 (11)	0.0598 (4)
H2A	0.5067	1.0426	0.2181	0.072*
C3	0.6017 (5)	1.02944 (9)	0.33542 (12)	0.0641 (5)
H3A	0.5426	1.0774	0.3487	0.077*
C4	0.7125 (5)	0.97907 (10)	0.39391 (11)	0.0629 (5)
H4A	0.7289	0.9935	0.4466	0.075*
C5	0.7998 (4)	0.90706 (9)	0.37484 (9)	0.0491 (3)
H5A	0.8769	0.8736	0.4145	0.059*
C6	0.7714 (3)	0.88523 (7)	0.29628 (7)	0.0370 (3)
C7	0.8527 (3)	0.80877 (7)	0.27359 (7)	0.0341 (2)
C8	0.9156 (3)	0.68630 (7)	0.26224 (8)	0.0388 (3)
H8A	0.9153	0.6349	0.2698	0.047*
C9	0.7949 (3)	0.73971 (7)	0.30963 (7)	0.0337 (2)
C10	0.6185 (3)	0.72707 (7)	0.37639 (7)	0.0358 (2)
H10A	0.5400	0.7671	0.4030	0.043*
C11	0.2728 (4)	0.58040 (7)	0.47418 (8)	0.0450 (3)
H11A	0.2897	0.5399	0.4410	0.054*
C12	0.3230 (3)	0.69554 (7)	0.52237 (7)	0.0335 (2)
H1N2	1.114 (5)	0.7046 (11)	0.1654 (12)	0.064 (6)*
H1N6	0.095 (5)	0.6601 (12)	0.6124 (12)	0.067 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0665 (2)	0.03563 (18)	0.04225 (19)	−0.01109 (15)	0.02386 (16)	−0.00666 (13)
N1	0.0537 (7)	0.0369 (6)	0.0350 (5)	−0.0016 (4)	0.0193 (5)	0.0000 (4)
N2	0.0546 (7)	0.0397 (6)	0.0357 (5)	0.0009 (5)	0.0210 (5)	−0.0030 (4)
N3	0.0492 (6)	0.0373 (5)	0.0323 (5)	0.0024 (4)	0.0192 (4)	0.0020 (4)
N4	0.0459 (6)	0.0294 (5)	0.0322 (5)	0.0016 (4)	0.0167 (4)	0.0020 (4)
N5	0.0741 (8)	0.0330 (6)	0.0443 (6)	−0.0067 (5)	0.0264 (6)	−0.0002 (4)
N6	0.0590 (7)	0.0339 (5)	0.0354 (5)	−0.0037 (5)	0.0225 (5)	−0.0012 (4)
C1	0.0609 (9)	0.0393 (7)	0.0429 (7)	0.0019 (6)	0.0128 (6)	0.0037 (5)
C2	0.0743 (11)	0.0391 (8)	0.0677 (10)	0.0064 (7)	0.0150 (9)	0.0070 (7)
C3	0.0760 (12)	0.0395 (8)	0.0797 (12)	0.0054 (8)	0.0213 (9)	−0.0107 (8)
C4	0.0801 (12)	0.0566 (10)	0.0543 (9)	−0.0021 (9)	0.0172 (8)	−0.0203 (8)
C5	0.0625 (9)	0.0468 (8)	0.0391 (7)	0.0006 (7)	0.0110 (6)	−0.0035 (6)
C6	0.0414 (6)	0.0348 (6)	0.0368 (6)	−0.0027 (5)	0.0134 (5)	−0.0009 (5)
C7	0.0393 (6)	0.0353 (6)	0.0294 (5)	−0.0010 (5)	0.0113 (4)	0.0006 (4)
C8	0.0462 (7)	0.0358 (6)	0.0366 (6)	−0.0001 (5)	0.0140 (5)	0.0002 (5)
C9	0.0375 (6)	0.0348 (6)	0.0306 (5)	0.0003 (4)	0.0115 (4)	0.0012 (4)
C10	0.0411 (6)	0.0366 (6)	0.0321 (5)	0.0030 (5)	0.0139 (5)	0.0021 (4)
C11	0.0695 (9)	0.0288 (6)	0.0409 (6)	−0.0015 (6)	0.0231 (6)	−0.0010 (5)
C12	0.0381 (6)	0.0336 (5)	0.0307 (5)	0.0010 (4)	0.0121 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C12	1.6735 (13)	C2—C3	1.372 (3)
N1—C7	1.3358 (15)	C2—H2A	0.9300
N1—N2	1.3516 (16)	C3—C4	1.380 (3)
N2—C8	1.3283 (17)	C3—H3A	0.9300
N2—H1N2	0.84 (2)	C4—C5	1.390 (2)
N3—C10	1.2731 (17)	C4—H4A	0.9300
N3—N4	1.3950 (14)	C5—C6	1.3880 (19)
N4—C11	1.3693 (16)	C5—H5A	0.9300
N4—C12	1.3830 (15)	C6—C7	1.4744 (17)
N5—C11	1.2905 (18)	C7—C9	1.4160 (17)
N5—N6	1.3700 (16)	C8—C9	1.3862 (17)
N6—C12	1.3433 (16)	C8—H8A	0.9300
N6—H1N6	0.90 (2)	C9—C10	1.4460 (16)
C1—C2	1.382 (2)	C10—H10A	0.9300
C1—C6	1.3916 (19)	C11—H11A	0.9300
C1—H1A	0.9300

C7—N1—N2	105.45 (10)	C6—C5—C4	119.74 (15)
C8—N2—N1	112.74 (11)	C6—C5—H5A	120.1
C8—N2—H1N2	128.2 (13)	C4—C5—H5A	120.1
N1—N2—H1N2	119.0 (13)	C5—C6—C1	118.92 (13)
C10—N3—N4	117.80 (11)	C5—C6—C7	121.48 (12)
C11—N4—C12	107.64 (10)	C1—C6—C7	119.60 (12)
C11—N4—N3	118.92 (10)	N1—C7—C9	110.02 (11)
C12—N4—N3	133.20 (10)	N1—C7—C6	120.03 (11)
C11—N5—N6	103.26 (11)	C9—C7—C6	129.93 (11)
C12—N6—N5	114.42 (11)	N2—C8—C9	106.89 (11)
C12—N6—H1N6	125.9 (14)	N2—C8—H8A	126.6
N5—N6—H1N6	119.6 (14)	C9—C8—H8A	126.6
C2—C1—C6	120.79 (15)	C8—C9—C7	104.90 (11)
C2—C1—H1A	119.6	C8—C9—C10	127.30 (12)
C6—C1—H1A	119.6	C7—C9—C10	127.52 (11)
C3—C2—C1	120.07 (16)	N3—C10—C9	119.17 (12)
C3—C2—H2A	120.0	N3—C10—H10A	120.4
C1—C2—H2A	120.0	C9—C10—H10A	120.4
C2—C3—C4	119.84 (15)	N5—C11—N4	112.28 (12)
C2—C3—H3A	120.1	N5—C11—H11A	123.9
C4—C3—H3A	120.1	N4—C11—H11A	123.9
C3—C4—C5	120.62 (16)	N6—C12—N4	102.40 (10)
C3—C4—H4A	119.7	N6—C12—S1	126.82 (9)
C5—C4—H4A	119.7	N4—C12—S1	130.77 (9)

C7—N1—N2—C8	0.32 (16)	N2—C8—C9—C7	−0.12 (15)
C10—N3—N4—C11	164.74 (13)	N2—C8—C9—C10	174.12 (13)
C10—N3—N4—C12	−21.8 (2)	N1—C7—C9—C8	0.33 (15)
C11—N5—N6—C12	−0.19 (18)	C6—C7—C9—C8	178.66 (13)
C6—C1—C2—C3	0.0 (3)	N1—C7—C9—C10	−173.91 (13)
C1—C2—C3—C4	0.8 (3)	C6—C7—C9—C10	4.4 (2)
C2—C3—C4—C5	−0.4 (3)	N4—N3—C10—C9	−178.11 (11)
C3—C4—C5—C6	−0.8 (3)	C8—C9—C10—N3	2.6 (2)
C4—C5—C6—C1	1.6 (2)	C7—C9—C10—N3	175.63 (13)
C4—C5—C6—C7	−178.29 (14)	N6—N5—C11—N4	0.09 (18)
C2—C1—C6—C5	−1.2 (2)	C12—N4—C11—N5	0.03 (18)
C2—C1—C6—C7	178.68 (15)	N3—N4—C11—N5	175.07 (12)
N2—N1—C7—C9	−0.39 (15)	N5—N6—C12—N4	0.20 (16)
N2—N1—C7—C6	−178.91 (12)	N5—N6—C12—S1	−179.73 (11)
C5—C6—C7—N1	−143.18 (14)	C11—N4—C12—N6	−0.14 (15)
C1—C6—C7—N1	36.93 (19)	N3—N4—C12—N6	−174.18 (13)
C5—C6—C7—C9	38.6 (2)	C11—N4—C12—S1	179.79 (12)
C1—C6—C7—C9	−141.26 (15)	N3—N4—C12—S1	5.8 (2)
N1—N2—C8—C9	−0.12 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.84 (2)	2.59 (2)	3.3593 (15)	153.6 (17)
N6—H1N6···N1ⁱⁱ	0.90 (2)	1.91 (2)	2.7884 (15)	168.0 (2)
C10—H10A···S1	0.93	2.50	3.2183 (13)	134

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₆S
M_r	270.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	4.1180 (4), 17.9237 (16), 17.0787 (15)
β (°)	97.352 (3)
V (Å³)	1250.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.55 × 0.26 × 0.19

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.872, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	14262, 4361, 3204
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.750

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.03
No. of reflections	4361
No. of parameters	180
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.84 (2)	2.59 (2)	3.3593 (15)	153.6 (17)
N6—H1N6···N1ⁱⁱ	0.90 (2)	1.91 (2)	2.7884 (15)	168.0 (2)
C10—H10A···S1	0.9300	2.5000	3.2183 (13)	134

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. AMI thanks the Board for Research in Nuclear Sciences, Government of India for a Young Scientist award.

References

Bekircan, O., Kahveci, B. & Kucuk, M. (2006). Turk. J. Chem. 30, 29–40. CAS Google Scholar
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Volume 67| Part 8| August 2011| Page o1944

doi:10.1107/S1600536811024834

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

4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl­­idene]amino}-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]amino}-1H-1,2,4-triazole-5(4H)-thione