4-[(E)-2,6-Dichloro­benzyl­ideneamino]-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Chantrapromma, S.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Muralidharan, A.; Dharmaprakash, S.M.

doi:10.1107/S1600536808021272

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1503-o1504

doi:10.1107/S1600536808021272

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4-[(E)-2,6-Dichlorobenzylideneamino]-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ K. V. Sujith,^c P. S. Patil,^d B. Kalluraya,^c A. Muralidharan ^e and S. M. Dharmaprakash ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^dDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^eDepartment of Chemistry, Nehru Arts & Science College, Kanhangad, Kerala 671 328, India
^*Correspondence e-mail: hkfun@usm.my

(Received 7 July 2008; accepted 9 July 2008; online 16 July 2008)

In the title Schiff base compound, C₂₁H₂₂Cl₂N₄S, the triazole ring makes dihedral angles of 2.15 (11) and 87.48 (11)° with the 2,6-dichlorophenyl and methylpropylphenyl rings, respectively. Weak intramolecular C—H⋯S and C—H⋯Cl interactions generate S(6) and S(5) ring motifs, respectively. In the crystal structure, centrosymmetrically related molecules are linked into dimers by N—H⋯S hydrogen bonds. These dimers are arranged into sheets parallel to the ab plane and are stacked along the c axis. C—H⋯π interactions involving the methylpropylphenyl ring and π–π interactions involving the dichlorophenyl ring [centroid–centroid distance = 3.5865 (3) Å] are also observed.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2008a ,b ). For background to the activities and applications of 1,2,4-triazole derivatives, see: Almasirad et al. (2004 ); Al-Soud et al. (2003 ); Amir & Shikha (2004 ); Holla et al. (2003 ); Kawashima et al. (1987 ); Palaska et al. (2002 ); Walczak et al. (2004 ); Zitouni et al. (2005 ).

Experimental

Crystal data

C₂₁H₂₂Cl₂N₄S
M_r = 433.40
Triclinic, $[P \overline 1]$
a = 8.6190 (2) Å
b = 9.4441 (2) Å
c = 14.4244 (4) Å
α = 104.669 (2)°
β = 95.492 (2)°
γ = 110.418 (1)°
V = 1042.33 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100.0 (1) K
0.29 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.887, T_max = 0.934
19865 measured reflections
6032 independent reflections
4139 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.00
6032 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1ⁱ	0.86	2.44	3.2849 (19)	169
C10—H10A⋯Cl2	0.93	2.62	2.978 (2)	104
C10—H10A⋯S1	0.93	2.52	3.2066 (19)	131
C15—H15A⋯Cg1ⁱⁱ	0.93	2.94	3.793 (3)	154
Symmetry codes: (i) -x+2, -y-1, -z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021272/ci2627sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021272/ci2627Isup2.hkl

checkCIF report

Comment top

1,2,4-Triazoles and their derivatives represent an overwhelming and rapid developing field in modern heterocyclic chemistry. A degree of respectability has been bestowed for 1,2,4-triazole derivatives due to their antibacterial, antifungal (Zitouni et al., 2005), antitubercular (Walczak et al., 2004), anticancer (Holla et al., 2003), antitumor (Al-Soud et al., 2003), anticonvulsant (Almasirad et al., 2004), antiinflammatory, and analgesic properties (Amir & Shikha, 2004). Certain 1,2,4-triazoles also find applications in the preparation of photographic plates, polymers, and as analytical agents (Kawashima et al., 1987). Similarly, ibuprofen belongs to the class of Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) with antipyretic, anti-inflammatory and analgesic properties (Palaska et al., 2002). Our earlier studies involved synthesis of heterocyclic compounds which contain in their structures both the ibuprofen and 1,2,4-triazole fragments (Fun et al., 2008a,b). In this connection and in continuation of our interest in the synthesis of chemically and biologically important heterocycles, we report here the crystal structure of a substituted 1,2,4-triazole Schiff base carrying only the ibuprofen moiety.

In the title Schiff base compound (Fig. 1), the 1,2,4 triazole ring (C8-C9/N1-N3) is planar with a maximum deviation of 0.009 (2) Å for atom N3. The 1,2,4 triazole ring is co-planar with the 2,6-dichlorophenyl (C11-C16) ring [dihedral angle = 2.15 (11)°] but is almost perpendicular to the methylpropylphenyl (C1-C6) ring with a dihedral angle of 87.48 (11)°. The methylidene amino linkage (N4/C10) is slightly twisted from the mean plane of the 1,2,4 triazole ring as indicated by the torsion angle C9–N3–N4–C10 of 26.4 (3)°. Weak C—H···S and C—H···Cl intramolecular interactions generate S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995). The bond distances and angles have normal values (Allen et al., 1987) and are comparable with closely related structures (Fun et al., 2008a,b).

In the crystal structure, centrosymmetrically related molecules are linked into dimers (Fig. 2) by N—H···S hydrogen bonds (Table 1). These dimers are arranged into sheets parallel to the ab plane and these sheets are stacked along the c axis (Fig. 3). In addition, the crystal structure is stabilized by C—H···π interactions (Table 1) involving the C1-C6 ring (centroid Cg1) and π-π interaction involving the C11-C16 ring (centroid Cg2) [Cg₂···Cg₂ⁱⁱ = 3.5865 (3) Å, symmetry code: (ii) 1 - x, -y, -z].

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2008a,b). For background to the activities and applications of 1,2,4-triazole derivatives, see: Almasirad et al. (2004); Al-Soud et al. (2003); Amir & Shikha (2004); Holla et al. (2003); Kawashima et al. (1987); Palaska et al. (2002); Walczak et al. (2004); Zitouni et al. (2005). Cg1 is the centroid of the C1–C6 ring.

Experimental top

The title compound was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 2,6-dichlorobenzaldehyde (0.01 mol) in ethanol (50 ml) with the addition of 3 drops of concentrated sulfuric acid for 3 h. The solid product obtained was collected by filtration, washed with ethanol and dried. Colourless single crystals suitable for X-ray analysis were obtained from a acetone-N,N-dimethylformamide (DMF) (1:3 v/v) solution by slow evaporation (yield 53%; m.p. 438–440 K)

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Weak C—H···S and C—H···Cl hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the crystal packing of the title compound, viewed along the a axis, showing hydrogen-bonded (dashed lines) dimers.
	Fig. 3. The packing diagram of the title compound, viewed along the c axis, showing stacking of the molecular sheets. Hydrogen bonds are shown as dashed lines.

4-[(E)-2,6-Dichlorobenzylideneamino]-3-{1-[4-(2- methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₁H₂₂Cl₂N₄S	Z = 2
M_r = 433.40	F(000) = 452
Triclinic, P1	D_x = 1.381 Mg m⁻³
Hall symbol: -P 1	Melting point = 438–440 K
a = 8.6190 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4441 (2) Å	Cell parameters from 6032 reflections
c = 14.4244 (4) Å	θ = 1.5–30.0°
α = 104.669 (2)°	µ = 0.43 mm⁻¹
β = 95.492 (2)°	T = 100 K
γ = 110.418 (1)°	Block, colourless
V = 1042.33 (5) Å³	0.29 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6032 independent reflections
Radiation source: fine-focus sealed tube	4139 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.887, T_max = 0.935	l = −20→19
19865 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0746P)²] where P = (F_o² + 2F_c²)/3
6032 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₁H₂₂Cl₂N₄S	γ = 110.418 (1)°
M_r = 433.40	V = 1042.33 (5) Å³
Triclinic, P1	Z = 2
a = 8.6190 (2) Å	Mo Kα radiation
b = 9.4441 (2) Å	µ = 0.43 mm⁻¹
c = 14.4244 (4) Å	T = 100 K
α = 104.669 (2)°	0.29 × 0.20 × 0.16 mm
β = 95.492 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6032 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4139 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.935	R_int = 0.050
19865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	Δρ_max = 0.59 e Å⁻³
6032 reflections	Δρ_min = −0.47 e Å⁻³
256 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.79027 (6)	−0.43005 (6)	−0.06227 (3)	0.02335 (13)
Cl1	0.43164 (7)	−0.07928 (7)	0.21127 (4)	0.03523 (15)
Cl2	0.41695 (7)	−0.33808 (6)	−0.17537 (4)	0.03136 (14)
N1	0.9611 (2)	−0.3270 (2)	0.21761 (12)	0.0244 (4)
N2	0.9465 (2)	−0.3961 (2)	0.11923 (12)	0.0240 (4)
H2A	1.0037	−0.4511	0.0971	0.029*
N3	0.7738 (2)	−0.28053 (18)	0.12730 (11)	0.0192 (3)
N4	0.6602 (2)	−0.20834 (19)	0.11584 (12)	0.0229 (4)
C1	0.9409 (2)	0.0211 (2)	0.32320 (13)	0.0218 (4)
C2	1.1052 (3)	0.0657 (2)	0.30759 (15)	0.0259 (4)
H2B	1.1515	−0.0105	0.2915	0.031*
C3	1.2013 (3)	0.2223 (2)	0.31568 (15)	0.0266 (4)
H3A	1.3109	0.2492	0.3046	0.032*
C4	1.1366 (3)	0.3403 (2)	0.34015 (14)	0.0244 (4)
C5	0.9747 (3)	0.2957 (2)	0.35952 (14)	0.0262 (4)
H5A	0.9301	0.3726	0.3786	0.031*
C6	0.8779 (3)	0.1389 (2)	0.35107 (14)	0.0234 (4)
H6A	0.7696	0.1125	0.3642	0.028*
C7	0.8319 (3)	−0.1523 (2)	0.31079 (14)	0.0225 (4)
H7A	0.7131	−0.1651	0.3013	0.027*
C8	0.8563 (2)	−0.2560 (2)	0.22068 (14)	0.0217 (4)
C9	0.8351 (2)	−0.3702 (2)	0.06064 (14)	0.0206 (4)
C10	0.5498 (2)	−0.2695 (2)	0.03633 (14)	0.0223 (4)
H10A	0.5495	−0.3578	−0.0105	0.027*
C11	0.4228 (2)	−0.2036 (2)	0.01691 (14)	0.0215 (4)
C12	0.3619 (3)	−0.1177 (2)	0.08757 (15)	0.0239 (4)
C13	0.2388 (3)	−0.0628 (2)	0.06263 (16)	0.0270 (4)
H13A	0.2011	−0.0054	0.1112	0.032*
C14	0.1729 (3)	−0.0938 (2)	−0.03479 (16)	0.0278 (5)
H14A	0.0906	−0.0570	−0.0516	0.033*
C15	0.2278 (3)	−0.1792 (3)	−0.10761 (16)	0.0284 (5)
H15A	0.1829	−0.2003	−0.1732	0.034*
C16	0.3504 (3)	−0.2325 (2)	−0.08126 (14)	0.0246 (4)
C17	1.2359 (3)	0.5077 (2)	0.34117 (15)	0.0281 (5)
H17A	1.1787	0.5286	0.2881	0.034*
H17B	1.3462	0.5147	0.3281	0.034*
C18	1.2612 (3)	0.6380 (2)	0.43631 (15)	0.0248 (4)
H18A	1.1498	0.6274	0.4512	0.030*
C19	1.3448 (3)	0.8002 (2)	0.42311 (17)	0.0331 (5)
H19A	1.3584	0.8813	0.4826	0.050*
H19B	1.2752	0.8098	0.3709	0.050*
H19C	1.4535	0.8121	0.4075	0.050*
C20	1.3655 (3)	0.6216 (3)	0.52176 (15)	0.0307 (5)
H20A	1.3751	0.7017	0.5808	0.046*
H20B	1.4763	0.6345	0.5092	0.046*
H20C	1.3109	0.5185	0.5289	0.046*
C21	0.8713 (3)	−0.2028 (3)	0.39995 (15)	0.0315 (5)
H21A	0.8010	−0.3124	0.3882	0.047*
H21B	0.8496	−0.1387	0.4564	0.047*
H21C	0.9880	−0.1890	0.4113	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0258 (3)	0.0241 (2)	0.0194 (2)	0.0112 (2)	0.00672 (19)	0.00244 (18)
Cl1	0.0389 (3)	0.0551 (4)	0.0221 (3)	0.0310 (3)	0.0104 (2)	0.0093 (2)
Cl2	0.0362 (3)	0.0338 (3)	0.0213 (3)	0.0135 (2)	0.0063 (2)	0.0036 (2)
N1	0.0296 (9)	0.0241 (8)	0.0190 (8)	0.0132 (7)	0.0055 (7)	0.0016 (7)
N2	0.0272 (9)	0.0240 (8)	0.0228 (8)	0.0152 (7)	0.0061 (7)	0.0030 (7)
N3	0.0210 (8)	0.0184 (7)	0.0182 (8)	0.0081 (6)	0.0061 (6)	0.0043 (6)
N4	0.0241 (8)	0.0230 (8)	0.0247 (9)	0.0120 (7)	0.0080 (7)	0.0072 (7)
C1	0.0245 (10)	0.0248 (10)	0.0144 (9)	0.0095 (8)	0.0034 (7)	0.0036 (7)
C2	0.0280 (10)	0.0235 (10)	0.0270 (11)	0.0134 (8)	0.0080 (8)	0.0033 (8)
C3	0.0245 (10)	0.0280 (10)	0.0245 (10)	0.0090 (8)	0.0086 (8)	0.0037 (8)
C4	0.0299 (10)	0.0252 (10)	0.0159 (9)	0.0108 (8)	0.0050 (8)	0.0023 (8)
C5	0.0293 (10)	0.0250 (10)	0.0242 (10)	0.0140 (8)	0.0062 (8)	0.0020 (8)
C6	0.0245 (10)	0.0261 (10)	0.0205 (9)	0.0124 (8)	0.0072 (8)	0.0037 (8)
C7	0.0251 (10)	0.0229 (9)	0.0195 (9)	0.0103 (8)	0.0064 (8)	0.0042 (7)
C8	0.0249 (10)	0.0194 (9)	0.0199 (9)	0.0075 (8)	0.0069 (7)	0.0051 (7)
C9	0.0227 (9)	0.0165 (8)	0.0212 (9)	0.0067 (7)	0.0071 (7)	0.0039 (7)
C10	0.0216 (9)	0.0203 (9)	0.0237 (10)	0.0066 (8)	0.0081 (8)	0.0054 (7)
C11	0.0192 (9)	0.0203 (9)	0.0235 (10)	0.0049 (7)	0.0062 (8)	0.0072 (7)
C12	0.0228 (10)	0.0270 (10)	0.0223 (10)	0.0093 (8)	0.0068 (8)	0.0082 (8)
C13	0.0225 (10)	0.0300 (11)	0.0323 (11)	0.0125 (8)	0.0106 (8)	0.0113 (9)
C14	0.0219 (10)	0.0300 (11)	0.0356 (12)	0.0107 (9)	0.0062 (9)	0.0158 (9)
C15	0.0274 (10)	0.0296 (11)	0.0255 (11)	0.0074 (9)	0.0028 (8)	0.0103 (8)
C16	0.0246 (10)	0.0244 (10)	0.0226 (10)	0.0065 (8)	0.0079 (8)	0.0064 (8)
C17	0.0349 (12)	0.0259 (10)	0.0224 (10)	0.0104 (9)	0.0104 (9)	0.0060 (8)
C18	0.0267 (10)	0.0220 (10)	0.0241 (10)	0.0086 (8)	0.0062 (8)	0.0053 (8)
C19	0.0390 (13)	0.0245 (10)	0.0335 (12)	0.0102 (10)	0.0105 (10)	0.0070 (9)
C20	0.0353 (12)	0.0306 (11)	0.0264 (11)	0.0164 (9)	0.0049 (9)	0.0046 (9)
C21	0.0416 (13)	0.0319 (11)	0.0234 (11)	0.0159 (10)	0.0103 (9)	0.0088 (9)

Geometric parameters (Å, º) top

S1—C9	1.6797 (19)	C10—C11	1.472 (3)
Cl1—C12	1.730 (2)	C10—H10A	0.93
Cl2—C16	1.740 (2)	C11—C12	1.398 (3)
N1—C8	1.297 (2)	C11—C16	1.409 (3)
N1—N2	1.377 (2)	C12—C13	1.389 (3)
N2—C9	1.345 (2)	C13—C14	1.381 (3)
N2—H2A	0.86	C13—H13A	0.93
N3—C8	1.384 (2)	C14—C15	1.382 (3)
N3—C9	1.385 (2)	C14—H14A	0.93
N3—N4	1.394 (2)	C15—C16	1.381 (3)
N4—C10	1.275 (2)	C15—H15A	0.93
C1—C2	1.388 (3)	C17—C18	1.531 (3)
C1—C6	1.390 (3)	C17—H17A	0.97
C1—C7	1.530 (3)	C17—H17B	0.97
C2—C3	1.388 (3)	C18—C19	1.519 (3)
C2—H2B	0.93	C18—C20	1.527 (3)
C3—C4	1.396 (3)	C18—H18A	0.98
C3—H3A	0.93	C19—H19A	0.96
C4—C5	1.388 (3)	C19—H19B	0.96
C4—C17	1.508 (3)	C19—H19C	0.96
C5—C6	1.389 (3)	C20—H20A	0.96
C5—H5A	0.93	C20—H20B	0.96
C6—H6A	0.93	C20—H20C	0.96
C7—C8	1.498 (3)	C21—H21A	0.96
C7—C21	1.529 (3)	C21—H21B	0.96
C7—H7A	0.98	C21—H21C	0.96

C8—N1—N2	104.17 (15)	C13—C12—Cl1	116.33 (16)
C9—N2—N1	114.24 (15)	C11—C12—Cl1	121.52 (16)
C9—N2—H2A	122.9	C14—C13—C12	119.57 (19)
N1—N2—H2A	122.9	C14—C13—H13A	120.2
C8—N3—C9	108.43 (15)	C12—C13—H13A	120.2
C8—N3—N4	119.01 (15)	C13—C14—C15	120.7 (2)
C9—N3—N4	132.41 (16)	C13—C14—H14A	119.6
C10—N4—N3	117.04 (16)	C15—C14—H14A	119.6
C2—C1—C6	117.99 (19)	C16—C15—C14	118.81 (19)
C2—C1—C7	121.30 (17)	C16—C15—H15A	120.6
C6—C1—C7	120.71 (18)	C14—C15—H15A	120.6
C1—C2—C3	121.00 (18)	C15—C16—C11	122.96 (19)
C1—C2—H2B	119.5	C15—C16—Cl2	117.26 (16)
C3—C2—H2B	119.5	C11—C16—Cl2	119.79 (16)
C2—C3—C4	121.3 (2)	C4—C17—C18	115.60 (17)
C2—C3—H3A	119.4	C4—C17—H17A	108.4
C4—C3—H3A	119.4	C18—C17—H17A	108.4
C5—C4—C3	117.32 (19)	C4—C17—H17B	108.4
C5—C4—C17	121.41 (18)	C18—C17—H17B	108.4
C3—C4—C17	121.22 (19)	H17A—C17—H17B	107.4
C4—C5—C6	121.51 (18)	C19—C18—C20	110.68 (17)
C4—C5—H5A	119.2	C19—C18—C17	109.89 (18)
C6—C5—H5A	119.2	C20—C18—C17	111.28 (17)
C5—C6—C1	120.83 (19)	C19—C18—H18A	108.3
C5—C6—H6A	119.6	C20—C18—H18A	108.3
C1—C6—H6A	119.6	C17—C18—H18A	108.3
C8—C7—C21	110.54 (16)	C18—C19—H19A	109.5
C8—C7—C1	108.88 (16)	C18—C19—H19B	109.5
C21—C7—C1	112.70 (16)	H19A—C19—H19B	109.5
C8—C7—H7A	108.2	C18—C19—H19C	109.5
C21—C7—H7A	108.2	H19A—C19—H19C	109.5
C1—C7—H7A	108.2	H19B—C19—H19C	109.5
N1—C8—N3	110.81 (16)	C18—C20—H20A	109.5
N1—C8—C7	126.05 (18)	C18—C20—H20B	109.5
N3—C8—C7	123.04 (17)	H20A—C20—H20B	109.5
N2—C9—N3	102.32 (15)	C18—C20—H20C	109.5
N2—C9—S1	127.33 (15)	H20A—C20—H20C	109.5
N3—C9—S1	130.33 (15)	H20B—C20—H20C	109.5
N4—C10—C11	121.60 (18)	C7—C21—H21A	109.5
N4—C10—H10A	119.2	C7—C21—H21B	109.5
C11—C10—H10A	119.2	H21A—C21—H21B	109.5
C12—C11—C16	115.84 (18)	C7—C21—H21C	109.5
C12—C11—C10	125.92 (18)	H21A—C21—H21C	109.5
C16—C11—C10	118.21 (17)	H21B—C21—H21C	109.5
C13—C12—C11	122.11 (19)

C8—N1—N2—C9	0.0 (2)	N1—N2—C9—N3	−1.0 (2)
C8—N3—N4—C10	−158.60 (18)	N1—N2—C9—S1	177.52 (14)
C9—N3—N4—C10	26.4 (3)	C8—N3—C9—N2	1.52 (19)
C6—C1—C2—C3	−2.6 (3)	N4—N3—C9—N2	176.87 (18)
C7—C1—C2—C3	177.75 (18)	C8—N3—C9—S1	−176.89 (16)
C1—C2—C3—C4	0.3 (3)	N4—N3—C9—S1	−1.5 (3)
C2—C3—C4—C5	2.3 (3)	N3—N4—C10—C11	179.51 (17)
C2—C3—C4—C17	−175.13 (19)	N4—C10—C11—C12	−26.3 (3)
C3—C4—C5—C6	−2.6 (3)	N4—C10—C11—C16	155.8 (2)
C17—C4—C5—C6	174.83 (19)	C16—C11—C12—C13	−0.6 (3)
C4—C5—C6—C1	0.3 (3)	C10—C11—C12—C13	−178.53 (19)
C2—C1—C6—C5	2.3 (3)	C16—C11—C12—Cl1	177.38 (15)
C7—C1—C6—C5	−178.04 (18)	C10—C11—C12—Cl1	−0.6 (3)
C2—C1—C7—C8	−42.3 (2)	C11—C12—C13—C14	0.3 (3)
C6—C1—C7—C8	138.03 (19)	Cl1—C12—C13—C14	−177.75 (16)
C2—C1—C7—C21	80.7 (2)	C12—C13—C14—C15	0.1 (3)
C6—C1—C7—C21	−98.9 (2)	C13—C14—C15—C16	−0.2 (3)
N2—N1—C8—N3	1.0 (2)	C14—C15—C16—C11	−0.1 (3)
N2—N1—C8—C7	−175.37 (18)	C14—C15—C16—Cl2	−179.50 (16)
C9—N3—C8—N1	−1.7 (2)	C12—C11—C16—C15	0.5 (3)
N4—N3—C8—N1	−177.76 (17)	C10—C11—C16—C15	178.60 (19)
C9—N3—C8—C7	174.84 (17)	C12—C11—C16—Cl2	179.88 (15)
N4—N3—C8—C7	−1.2 (3)	C10—C11—C16—Cl2	−2.0 (2)
C21—C7—C8—N1	−29.1 (3)	C5—C4—C17—C18	56.3 (3)
C1—C7—C8—N1	95.2 (2)	C3—C4—C17—C18	−126.4 (2)
C21—C7—C8—N3	154.92 (18)	C4—C17—C18—C19	−173.51 (18)
C1—C7—C8—N3	−80.8 (2)	C4—C17—C18—C20	63.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ⁱ	0.86	2.44	3.2849 (19)	169
C10—H10A···Cl2	0.93	2.62	2.978 (2)	104
C10—H10A···S1	0.93	2.52	3.2066 (19)	131
C15—H15A···Cg1ⁱⁱ	0.93	2.94	3.793 (3)	154

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂Cl₂N₄S
M_r	433.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6190 (2), 9.4441 (2), 14.4244 (4)
α, β, γ (°)	104.669 (2), 95.492 (2), 110.418 (1)
V (Å³)	1042.33 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.29 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.887, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	19865, 6032, 4139
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.00
No. of reflections	6032
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.47

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ⁱ	0.86	2.44	3.2849 (19)	169
C10—H10A···Cl2	0.93	2.62	2.978 (2)	104
C10—H10A···S1	0.93	2.52	3.2066 (19)	131
C15—H15A···Cg1ⁱⁱ	0.93	2.94	3.793 (3)	154

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

KVS, BK and AM are grateful to Kerala State Council for Science Technology and Environment, Thiruvananthapuram, for financial assistance. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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Volume 64| Part 8| August 2008| Pages o1503-o1504

doi:10.1107/S1600536808021272

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

4-[(E)-2,6-Di­chloro­benzyl­­idene­amino]-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-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)-2,6-Dichlorobenzylideneamino]-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione