rac-4-Amino-1-(2-benzoyl-1-phenyl­eth­yl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione

Wang, W.; Gao, Y.; Xiao, Z.; Yao, H.; Zhang, J.

doi:10.1107/S1600536810054255

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o348

doi:10.1107/S1600536810054255

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rac-4-Amino-1-(2-benzoyl-1-phenylethyl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione

Wei Wang,^a,^b Yan Gao,^b Zuo-bing Xiao,^a ^* Hong-guo Yao ^b and Jing-jing Zhang ^b

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 8 December 2010; accepted 25 December 2010; online 12 January 2011)

The title compound, C₁₈H₁₈N₄OS, has an almost planar 1,2,4-triazole ring [r.m.s. deviation = 0.0036 (2) Å], which makes dihedral angles of 78.5 (2) and 77.6 (11)° with the two phenyl rings. An intramolecular N—H⋯S interaction occurs. In the crystal, molecules are linked by an intermolecular three-centre N—H⋯(O,S) cyclic hydrogen-bonding interaction.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For the crystal structures of isomers of the title compound, see: Özel Güven et al. (2008a ,b ). For the pharmacological properties of triazole compounds, see: Paulvannan et al. (2001 ); Wahbi et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₈N₄OS
M_r = 338.42
Orthorhombic, P b c a
a = 17.604 (4) Å
b = 10.199 (2) Å
c = 19.241 (4) Å
V = 3454.5 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.954, T_max = 0.980
25430 measured reflections
3040 independent reflections
2527 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.137
S = 1.13
3040 reflections
227 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.90 (2)	2.47 (2)	3.121 (3)	129 (2)
N1—H1A⋯S1	0.90 (2)	2.65 (3)	3.195 (2)	120 (2)
N1—H1B⋯S1ⁱ	0.90 (2)	2.45 (1)	3.340 (3)	172 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054255/zs2086sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054255/zs2086Isup2.hkl

checkCIF report

Comment top

Functionalized 1,2,4-triazole derivatives are biologically interesting molecules and their chemistry is receiving considerable attention due to antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001; Wahbi et al., 1995). Some crystal structures of 1H-1,2,4-triazole ring-containing ether derivatives have been reported recently (Özel Güven, et al., 2008a, b). Here we report the synthesis and crystal structure of the title compound, rac-4-amino-1-[(1,3-diphenylpropan-1-one)-3-yl]-3-methyl-1H-1,2,4-triazole-5(4H)-thione (I) (Fig. 1).

The bond lengths and angles in (I) are found to have normal values (Allen et al., 1987). The 1,2,4-triazole ring (N2/C16/N3/N4/C17) is essentially planar with an r.m.s. deviation of 0.0036 (2)Å and a maximum deviation of 0.0057 (2)Å for atom N3. The two phenyl rings are inclined with respect to the 1,2,4-triazole ring [dihedral angles of 101.5 (2)° (C1–C6) and 102.4 (11)° (C10—C15)] with a dihedral angle between the two phenyl rings of 97.6°, which indicates that they are almost mutually perpendicular. In the crystal structure there is an intramolecular N—H···S interaction and the molecules are linked by an intermolecular three-centre N—H···O, N—H···S cyclic hydrogen-bonding interaction (Table 1).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For the crystal structures of isomers of the title compound, see: Özel Güven et al. (2008a,b). For the pharmacological properties of triazole compounds, see: Paulvannan et al. (2001); Wahbi et al. (1995).

Experimental top

The title compound was synthesized by the reaction of 1,3-diphenyl-2-propen-1-one (chalcone) (2.0 mmol) with 4-amino-1-methyl-4H-1,2,4-triazole-5-thiol (2.0 mmol) in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 90% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

rac-4-Amino-1-(2-benzoyl-1-phenylethyl)-3-methyl-1H- 1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₈H₁₈N₄OS	F(000) = 1424
M_r = 338.42	D_x = 1.301 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7030 reflections
a = 17.604 (4) Å	θ = 2.1–27.9°
b = 10.199 (2) Å	µ = 0.20 mm⁻¹
c = 19.241 (4) Å	T = 293 K
V = 3454.5 (13) Å³	Prism, colorless
Z = 8	0.24 × 0.22 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3040 independent reflections
Radiation source: rotating anode X-ray tube	2527 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.057
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→11
T_min = 0.954, T_max = 0.980	l = −22→22
25430 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.060P)² + 1.1394P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.001
3040 reflections	Δρ_max = 0.39 e Å⁻³
227 parameters	Δρ_min = −0.29 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0148 (12)

Crystal data top

C₁₈H₁₈N₄OS	V = 3454.5 (13) Å³
M_r = 338.42	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.604 (4) Å	µ = 0.20 mm⁻¹
b = 10.199 (2) Å	T = 293 K
c = 19.241 (4) Å	0.24 × 0.22 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3040 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2527 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.980	R_int = 0.057
25430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	3 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.39 e Å⁻³
3040 reflections	Δρ_min = −0.29 e Å⁻³
227 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	0.20040 (3)	0.45904 (6)	0.42466 (4)	0.0526 (2)
O1	0.38811 (10)	0.67534 (18)	0.34992 (8)	0.0550 (5)
N1	0.28460 (14)	0.2386 (2)	0.33526 (11)	0.0550 (6)
H1A	0.2383 (9)	0.276 (2)	0.3333 (17)	0.101 (13)*
H1B	0.2847 (14)	0.1601 (16)	0.3563 (14)	0.074 (10)*
N2	0.32401 (11)	0.31994 (19)	0.38230 (9)	0.0437 (5)
N3	0.35336 (10)	0.47896 (19)	0.44806 (10)	0.0427 (5)
N4	0.42070 (11)	0.4176 (2)	0.43219 (10)	0.0494 (5)
C1	0.49061 (13)	0.8173 (2)	0.37434 (12)	0.0472 (6)
C2	0.49301 (16)	0.8628 (3)	0.30604 (13)	0.0598 (7)
H2	0.4568	0.8345	0.2742	0.072*
C3	0.54873 (19)	0.9494 (3)	0.28535 (17)	0.0732 (9)
H3	0.5496	0.9796	0.2398	0.088*
C4	0.60258 (19)	0.9911 (3)	0.33125 (19)	0.0778 (9)
H4	0.6403	1.0486	0.3167	0.093*
C5	0.60126 (18)	0.9482 (3)	0.39905 (19)	0.0754 (9)
H5	0.6379	0.9771	0.4303	0.091*
C6	0.54545 (15)	0.8625 (3)	0.42060 (14)	0.0606 (7)
H6	0.5445	0.8345	0.4666	0.073*
C7	0.43012 (13)	0.7222 (2)	0.39396 (12)	0.0439 (6)
C8	0.42195 (13)	0.6852 (2)	0.46984 (11)	0.0438 (6)
H8A	0.4203	0.7649	0.4974	0.053*
H8B	0.4666	0.6363	0.4839	0.053*
C9	0.35175 (12)	0.6038 (2)	0.48612 (11)	0.0421 (6)
H9	0.3075	0.6531	0.4696	0.051*
C10	0.34152 (13)	0.5820 (3)	0.56370 (12)	0.0451 (6)
C11	0.30483 (17)	0.6765 (3)	0.60210 (14)	0.0659 (8)
H11	0.2866	0.7518	0.5804	0.079*
C12	0.2949 (2)	0.6597 (4)	0.67341 (15)	0.0805 (10)
H12	0.2703	0.7239	0.6994	0.097*
C13	0.32127 (19)	0.5483 (4)	0.70528 (15)	0.0757 (9)
H13	0.3153	0.5376	0.7530	0.091*
C14	0.3560 (2)	0.4543 (4)	0.66734 (16)	0.0847 (11)
H14	0.3729	0.3781	0.6890	0.102*
C15	0.36657 (19)	0.4705 (3)	0.59659 (15)	0.0734 (9)
H15	0.3908	0.4053	0.5711	0.088*
C16	0.29294 (13)	0.4212 (2)	0.41909 (11)	0.0399 (5)
C17	0.40078 (14)	0.3207 (2)	0.39139 (12)	0.0463 (6)
C18	0.45268 (16)	0.2216 (3)	0.36137 (14)	0.0629 (7)
H18A	0.5043	0.2491	0.3679	0.094*
H18B	0.4425	0.2124	0.3126	0.094*
H18C	0.4448	0.1389	0.3841	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0435 (4)	0.0467 (4)	0.0676 (5)	−0.0016 (3)	0.0024 (3)	−0.0004 (3)
O1	0.0561 (10)	0.0622 (12)	0.0466 (9)	−0.0008 (9)	−0.0050 (8)	−0.0057 (8)
N1	0.0718 (16)	0.0453 (13)	0.0480 (12)	−0.0055 (12)	−0.0067 (11)	−0.0062 (11)
N2	0.0536 (12)	0.0386 (11)	0.0389 (10)	0.0011 (9)	0.0004 (9)	−0.0008 (8)
N3	0.0411 (10)	0.0400 (11)	0.0471 (10)	0.0049 (9)	−0.0014 (8)	−0.0054 (9)
N4	0.0436 (11)	0.0500 (12)	0.0546 (12)	0.0091 (10)	−0.0012 (9)	−0.0044 (10)
C1	0.0458 (13)	0.0443 (14)	0.0516 (13)	0.0069 (11)	0.0028 (11)	−0.0015 (11)
C2	0.0646 (17)	0.0625 (18)	0.0523 (15)	0.0018 (14)	0.0085 (12)	−0.0003 (13)
C3	0.088 (2)	0.067 (2)	0.0651 (18)	−0.0005 (17)	0.0245 (17)	0.0058 (15)
C4	0.072 (2)	0.065 (2)	0.096 (3)	−0.0128 (17)	0.0255 (19)	−0.0014 (19)
C5	0.0619 (18)	0.069 (2)	0.095 (2)	−0.0124 (16)	−0.0030 (17)	−0.0063 (18)
C6	0.0596 (16)	0.0580 (17)	0.0643 (16)	−0.0044 (14)	−0.0049 (13)	0.0019 (14)
C7	0.0435 (12)	0.0415 (14)	0.0468 (13)	0.0089 (10)	−0.0006 (11)	−0.0033 (11)
C8	0.0471 (13)	0.0409 (13)	0.0436 (12)	0.0029 (10)	−0.0041 (10)	−0.0034 (11)
C9	0.0439 (12)	0.0376 (13)	0.0449 (12)	0.0052 (10)	−0.0025 (10)	−0.0056 (10)
C10	0.0422 (12)	0.0485 (15)	0.0447 (13)	−0.0018 (11)	−0.0007 (10)	−0.0036 (11)
C11	0.090 (2)	0.0536 (17)	0.0543 (15)	0.0102 (15)	0.0103 (14)	−0.0033 (13)
C12	0.112 (3)	0.074 (2)	0.0549 (17)	0.001 (2)	0.0184 (17)	−0.0141 (17)
C13	0.094 (2)	0.089 (3)	0.0440 (15)	−0.0094 (19)	0.0060 (15)	0.0011 (16)
C14	0.113 (3)	0.087 (3)	0.0544 (17)	0.024 (2)	−0.0020 (17)	0.0179 (17)
C15	0.097 (2)	0.069 (2)	0.0545 (16)	0.0295 (18)	0.0053 (16)	0.0062 (15)
C16	0.0474 (13)	0.0335 (12)	0.0387 (11)	−0.0001 (10)	0.0002 (9)	0.0024 (10)
C17	0.0534 (14)	0.0430 (14)	0.0426 (12)	0.0083 (11)	0.0018 (11)	0.0015 (11)
C18	0.0720 (18)	0.0550 (17)	0.0616 (16)	0.0157 (14)	0.0100 (14)	−0.0065 (14)

Geometric parameters (Å, º) top

S1—C16	1.678 (2)	C6—H6	0.9300
O1—C7	1.222 (3)	C7—C8	1.515 (3)
N1—N2	1.410 (3)	C8—C9	1.521 (3)
N1—H1A	0.900 (10)	C8—H8A	0.9700
N1—H1B	0.897 (10)	C8—H8B	0.9700
N2—C17	1.363 (3)	C9—C10	1.520 (3)
N2—C16	1.366 (3)	C9—H9	0.9800
N3—C16	1.338 (3)	C10—C15	1.375 (4)
N3—N4	1.375 (3)	C10—C11	1.375 (4)
N3—C9	1.469 (3)	C11—C12	1.394 (4)
N4—C17	1.310 (3)	C11—H11	0.9300
C1—C6	1.392 (3)	C12—C13	1.372 (5)
C1—C2	1.394 (3)	C12—H12	0.9300
C1—C7	1.489 (3)	C13—C14	1.351 (5)
C2—C3	1.379 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.384 (4)
C3—C4	1.363 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.376 (5)	C17—C18	1.480 (3)
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.379 (4)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600

N2—N1—H1A	103 (2)	N3—C9—C10	111.4 (2)
N2—N1—H1B	103.5 (19)	N3—C9—C8	110.77 (17)
H1A—N1—H1B	113.5 (16)	C10—C9—C8	112.23 (18)
C17—N2—C16	109.03 (19)	N3—C9—H9	107.4
C17—N2—N1	125.0 (2)	C10—C9—H9	107.4
C16—N2—N1	125.5 (2)	C8—C9—H9	107.4
C16—N3—N4	113.11 (19)	C15—C10—C11	118.9 (2)
C16—N3—C9	125.05 (18)	C15—C10—C9	122.3 (2)
N4—N3—C9	121.46 (18)	C11—C10—C9	118.7 (2)
C17—N4—N3	104.22 (19)	C10—C11—C12	120.1 (3)
C6—C1—C2	118.2 (2)	C10—C11—H11	119.9
C6—C1—C7	123.3 (2)	C12—C11—H11	119.9
C2—C1—C7	118.5 (2)	C13—C12—C11	119.9 (3)
C3—C2—C1	120.4 (3)	C13—C12—H12	120.0
C3—C2—H2	119.8	C11—C12—H12	120.0
C1—C2—H2	119.8	C14—C13—C12	120.0 (3)
C4—C3—C2	120.5 (3)	C14—C13—H13	120.0
C4—C3—H3	119.8	C12—C13—H13	120.0
C2—C3—H3	119.8	C13—C14—C15	120.5 (3)
C3—C4—C5	120.2 (3)	C13—C14—H14	119.7
C3—C4—H4	119.9	C15—C14—H14	119.7
C5—C4—H4	119.9	C10—C15—C14	120.5 (3)
C4—C5—C6	119.9 (3)	C10—C15—H15	119.7
C4—C5—H5	120.1	C14—C15—H15	119.7
C6—C5—H5	120.1	N3—C16—N2	103.33 (19)
C5—C6—C1	120.8 (3)	N3—C16—S1	130.09 (18)
C5—C6—H6	119.6	N2—C16—S1	126.58 (18)
C1—C6—H6	119.6	N4—C17—N2	110.3 (2)
O1—C7—C1	120.8 (2)	N4—C17—C18	125.7 (2)
O1—C7—C8	120.9 (2)	N2—C17—C18	123.9 (2)
C1—C7—C8	118.3 (2)	C17—C18—H18A	109.5
C7—C8—C9	114.30 (19)	C17—C18—H18B	109.5
C7—C8—H8A	108.7	H18A—C18—H18B	109.5
C9—C8—H8A	108.7	C17—C18—H18C	109.5
C7—C8—H8B	108.7	H18A—C18—H18C	109.5
C9—C8—H8B	108.7	H18B—C18—H18C	109.5
H8A—C8—H8B	107.6

C16—N3—N4—C17	1.0 (3)	N3—C9—C10—C11	−150.2 (2)
C9—N3—N4—C17	−172.2 (2)	C8—C9—C10—C11	84.9 (3)
C6—C1—C2—C3	0.4 (4)	C15—C10—C11—C12	1.3 (4)
C7—C1—C2—C3	−179.0 (2)	C9—C10—C11—C12	−179.7 (3)
C1—C2—C3—C4	0.5 (4)	C10—C11—C12—C13	−0.4 (5)
C2—C3—C4—C5	−0.8 (5)	C11—C12—C13—C14	−0.9 (5)
C3—C4—C5—C6	0.3 (5)	C12—C13—C14—C15	1.3 (6)
C4—C5—C6—C1	0.7 (5)	C11—C10—C15—C14	−0.9 (5)
C2—C1—C6—C5	−1.0 (4)	C9—C10—C15—C14	−179.9 (3)
C7—C1—C6—C5	178.5 (3)	C13—C14—C15—C10	−0.4 (6)
C6—C1—C7—O1	−172.5 (2)	N4—N3—C16—N2	−1.0 (2)
C2—C1—C7—O1	7.0 (3)	C9—N3—C16—N2	171.9 (2)
C6—C1—C7—C8	7.6 (3)	N4—N3—C16—S1	178.93 (17)
C2—C1—C7—C8	−173.0 (2)	C9—N3—C16—S1	−8.1 (4)
O1—C7—C8—C9	−8.5 (3)	C17—N2—C16—N3	0.7 (2)
C1—C7—C8—C9	171.4 (2)	N1—N2—C16—N3	−171.6 (2)
C16—N3—C9—C10	93.1 (3)	C17—N2—C16—S1	−179.32 (18)
N4—N3—C9—C10	−94.6 (2)	N1—N2—C16—S1	8.4 (3)
C16—N3—C9—C8	−141.2 (2)	N3—N4—C17—N2	−0.6 (3)
N4—N3—C9—C8	31.1 (3)	N3—N4—C17—C18	−178.0 (2)
C7—C8—C9—N3	61.1 (2)	C16—N2—C17—N4	−0.1 (3)
C7—C8—C9—C10	−173.70 (19)	N1—N2—C17—N4	172.2 (2)
N3—C9—C10—C15	28.7 (3)	C16—N2—C17—C18	177.4 (2)
C8—C9—C10—C15	−96.1 (3)	N1—N2—C17—C18	−10.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.90 (2)	2.47 (2)	3.121 (3)	129 (2)
N1—H1A···S1	0.90 (2)	2.65 (3)	3.195 (2)	120 (2)
N1—H1B···S1ⁱ	0.90 (2)	2.45 (1)	3.340 (3)	172 (2)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄OS
M_r	338.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	17.604 (4), 10.199 (2), 19.241 (4)
V (Å³)	3454.5 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.24 × 0.22 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.954, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	25430, 3040, 2527
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.137, 1.13
No. of reflections	3040
No. of parameters	227
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.901 (17)	2.472 (17)	3.121 (3)	129.3 (17)
N1—H1A···S1	0.901 (17)	2.65 (3)	3.195 (2)	120 (2)
N1—H1B···S1ⁱ	0.897 (19)	2.45 (1)	3.340 (3)	171.6 (19)

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

We gratefully acknowledge support of this project by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Özel Güven, Ö., Tahtacı, H., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1914–o1915. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özel Güven, Ö., Tahtacı, H., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1254. Web of Science CSD CrossRef IUCr Journals Google Scholar
Paulvannan, K., Hale, R., Sedehi, D. & Chen, T. (2001). Tetrahedron 57, 9677–9682. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wahbi, Y., Caujolle, R., Tournaire, C., Payard, M., Linas, M. D. & Seguela, J. P. (1995). Eur. J. Med. Chem. 30, 955–962. CrossRef CAS Web of Science Google Scholar

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Volume 67| Part 2| February 2011| Page o348

doi:10.1107/S1600536810054255

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

rac-4-Amino-1-(2-benzoyl-1-phenyl­eth­yl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-4-Amino-1-(2-benzoyl-1-phenylethyl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione