rac-4-Amino-1-(2-benzoyl-1-phenyl-eth-yl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

The title compound, C(18)H(18)N(4)OS, 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 intra-molecular N-H⋯S inter-action occurs. In the crystal, mol-ecules are linked by an inter-molecular three-centre N-H⋯(O,S) cyclic hydrogen-bonding inter-action.

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 = 338.42

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.137

S = 1.13

3040 reflections

227 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

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

C18H18N4OS	F(000) = 1424
Mr = 338.42	Dx = 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

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

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(Fo2) + (0.060P)2 + 1.1394P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
3040 reflections	Δρmax = 0.39 e Å−3
227 parameters	Δρmin = −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)

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	0.20040 (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*

	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)

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)

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)

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) .