4-Benzyl-1-p-tolyl-1H-1,2,4-triazol-5(4H)-one.

In the title compound, C(16)H(15)N(3)O, the triazole ring makes dihedral angles of 7.08 (2) and 74.53 (3)° with the two outer aromatic rings. The crystal packing is stabilized by very short inter-molecular C-H⋯O hydrogen bonds and weak π-π stacking inter-actions [centroid-to-centroid distance 3.632 (3) Å], resulting in the formation of zigzag chains parallel to the b axis.

Related literature

For details of the biological activity of tris­ubstituted triazol­inones, see: Chang et al. (1993 ▶, 1994 ▶). For bond-length data, see: Allen et al. (1987 ▶). For details of synthesis, see: Theodoridis (1998 ▶).

Experimental

Crystal data

C16H15N3O

M = 265.31

Monoclinic,

a = 4.6130 (9) Å

b = 25.488 (5) Å

c = 11.460 (2) Å

β = 96.18 (3)°

V = 1339.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 113 (2) K

0.18 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.985, T max = 0.997

9828 measured reflections

2333 independent reflections

1998 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.150

S = 1.10

2333 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002487/hg2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002487/hg2470Isup2.hkl

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

C16H15N3O	F(000) = 560
Mr = 265.31	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2910 reflections
a = 4.6130 (9) Å	θ = 1.6–27.9°
b = 25.488 (5) Å	µ = 0.09 mm−1
c = 11.460 (2) Å	T = 113 K
β = 96.18 (3)°	Block, colourless
V = 1339.6 (5) Å3	0.18 × 0.04 × 0.04 mm
Z = 4

Rigaku Saturn diffractometer	2333 independent reflections
Radiation source: rotating anode	1998 reflections with I > 2σ(I)
confocal	Rint = 0.052
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −5→5
Tmin = 0.985, Tmax = 0.997	k = −30→30
9828 measured reflections	l = −13→13

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-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0922P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2333 reflections	Δρmax = 0.23 e Å−3
183 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (5)

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
O1	0.4812 (3)	0.20822 (5)	0.27648 (11)	0.0298 (4)
N1	0.5904 (3)	0.17809 (5)	0.09066 (12)	0.0250 (4)
N2	0.5011 (4)	0.19124 (6)	−0.02578 (13)	0.0328 (4)
N3	0.2711 (3)	0.24033 (5)	0.09506 (13)	0.0267 (4)
C1	0.7986 (4)	0.13699 (6)	0.11575 (15)	0.0247 (4)
C2	0.8840 (4)	0.10765 (7)	0.02333 (16)	0.0295 (5)
H2	0.8061	0.1147	−0.0533	0.035*
C3	1.0867 (4)	0.06763 (7)	0.04622 (16)	0.0310 (5)
H3	1.1441	0.0483	−0.0162	0.037*
C4	1.2065 (4)	0.05553 (7)	0.15959 (17)	0.0281 (5)
C5	1.1164 (4)	0.08567 (7)	0.25051 (17)	0.0305 (5)
H5	1.1928	0.0784	0.3272	0.037*
C6	0.9155 (4)	0.12638 (7)	0.23019 (16)	0.0284 (5)
H6	0.8605	0.1462	0.2923	0.034*
C7	1.4263 (4)	0.01155 (7)	0.18258 (18)	0.0337 (5)
H7A	1.6175	0.0243	0.1720	0.051*
H7B	1.3764	−0.0167	0.1287	0.051*
H7C	1.4243	−0.0009	0.2616	0.051*
C8	0.4527 (4)	0.20823 (6)	0.16844 (16)	0.0242 (4)
C9	0.3125 (4)	0.22863 (7)	−0.01808 (17)	0.0328 (5)
H9	0.2161	0.2456	−0.0828	0.039*
C10	0.0864 (4)	0.28203 (7)	0.13604 (18)	0.0306 (5)
H10A	0.0539	0.2752	0.2169	0.037*
H10B	−0.1016	0.2817	0.0891	0.037*
C11	0.2243 (4)	0.33566 (7)	0.12782 (15)	0.0265 (5)
C12	0.4397 (4)	0.35251 (7)	0.21405 (16)	0.0326 (5)
H12	0.4966	0.3310	0.2779	0.039*
C13	0.5705 (5)	0.40130 (8)	0.20553 (18)	0.0370 (5)
H13	0.7158	0.4121	0.2631	0.044*
C14	0.4840 (5)	0.43383 (7)	0.11114 (17)	0.0374 (5)
H14	0.5691	0.4667	0.1057	0.045*
C15	0.2713 (5)	0.41719 (8)	0.02540 (18)	0.0388 (5)
H15	0.2142	0.4389	−0.0381	0.047*
C16	0.1420 (4)	0.36866 (7)	0.03274 (17)	0.0328 (5)
H16	−0.0006	0.3579	−0.0259	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0334 (8)	0.0304 (7)	0.0250 (7)	0.0016 (5)	0.0005 (6)	−0.0033 (5)
N1	0.0277 (9)	0.0245 (8)	0.0224 (8)	0.0005 (6)	0.0004 (6)	0.0006 (6)
N2	0.0443 (10)	0.0300 (9)	0.0235 (9)	0.0029 (8)	0.0013 (7)	0.0019 (7)
N3	0.0273 (9)	0.0239 (8)	0.0284 (9)	0.0020 (6)	0.0012 (7)	0.0001 (6)
C1	0.0235 (10)	0.0226 (9)	0.0282 (10)	−0.0032 (7)	0.0032 (8)	0.0008 (7)
C2	0.0331 (11)	0.0297 (10)	0.0266 (10)	−0.0023 (8)	0.0066 (8)	0.0018 (7)
C3	0.0328 (11)	0.0295 (10)	0.0326 (11)	−0.0003 (8)	0.0125 (9)	−0.0039 (8)
C4	0.0217 (10)	0.0250 (9)	0.0384 (11)	−0.0046 (7)	0.0063 (8)	0.0005 (8)
C5	0.0273 (11)	0.0337 (11)	0.0295 (10)	−0.0012 (8)	−0.0012 (8)	0.0006 (8)
C6	0.0288 (11)	0.0274 (10)	0.0285 (11)	0.0000 (8)	0.0013 (8)	−0.0038 (7)
C7	0.0286 (11)	0.0288 (10)	0.0440 (12)	0.0015 (8)	0.0053 (9)	0.0009 (9)
C8	0.0244 (10)	0.0217 (9)	0.0258 (10)	−0.0045 (7)	0.0002 (7)	−0.0009 (7)
C9	0.0377 (12)	0.0308 (10)	0.0287 (11)	0.0021 (8)	−0.0019 (9)	0.0032 (8)
C10	0.0258 (11)	0.0271 (10)	0.0395 (11)	0.0012 (8)	0.0056 (9)	0.0002 (8)
C11	0.0265 (10)	0.0251 (9)	0.0292 (10)	0.0033 (7)	0.0088 (8)	−0.0008 (7)
C12	0.0383 (12)	0.0303 (10)	0.0292 (10)	0.0032 (8)	0.0035 (9)	−0.0023 (8)
C13	0.0376 (12)	0.0362 (11)	0.0365 (12)	−0.0032 (9)	0.0013 (9)	−0.0107 (9)
C14	0.0443 (13)	0.0280 (10)	0.0421 (13)	−0.0082 (9)	0.0151 (10)	−0.0037 (9)
C15	0.0486 (14)	0.0325 (11)	0.0360 (12)	−0.0005 (9)	0.0075 (10)	0.0066 (9)
C16	0.0332 (12)	0.0321 (10)	0.0319 (11)	0.0009 (8)	−0.0008 (9)	0.0002 (8)

O1—C8	1.231 (2)	C7—H7A	0.9600
N1—C8	1.382 (2)	C7—H7B	0.9600
N1—N2	1.394 (2)	C7—H7C	0.9600
N1—C1	1.429 (2)	C9—H9	0.9300
N2—C9	1.299 (2)	C10—C11	1.515 (2)
N3—C9	1.364 (2)	C10—H10A	0.9700
N3—C8	1.388 (2)	C10—H10B	0.9700
N3—C10	1.471 (2)	C11—C12	1.392 (3)
C1—C2	1.388 (2)	C11—C16	1.397 (3)
C1—C6	1.390 (2)	C12—C13	1.390 (3)
C2—C3	1.390 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.387 (3)
C3—C4	1.391 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.379 (3)
C4—C5	1.394 (3)	C14—H14	0.9300
C4—C7	1.516 (2)	C15—C16	1.379 (3)
C5—C6	1.394 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300
C8—N1—N2	112.01 (14)	O1—C8—N1	129.94 (16)
C8—N1—C1	128.55 (15)	O1—C8—N3	126.98 (16)
N2—N1—C1	119.43 (14)	N1—C8—N3	103.07 (15)
C9—N2—N1	104.01 (15)	N2—C9—N3	112.84 (16)
C9—N3—C8	108.06 (15)	N2—C9—H9	123.6
C9—N3—C10	127.37 (16)	N3—C9—H9	123.6
C8—N3—C10	124.41 (15)	N3—C10—C11	111.73 (14)
C2—C1—C6	120.14 (16)	N3—C10—H10A	109.3
C2—C1—N1	118.77 (16)	C11—C10—H10A	109.3
C6—C1—N1	121.10 (15)	N3—C10—H10B	109.3
C1—C2—C3	119.47 (17)	C11—C10—H10B	109.3
C1—C2—H2	120.3	H10A—C10—H10B	107.9
C3—C2—H2	120.3	C12—C11—C16	118.79 (17)
C2—C3—C4	122.05 (17)	C12—C11—C10	120.45 (16)
C2—C3—H3	119.0	C16—C11—C10	120.75 (17)
C4—C3—H3	119.0	C13—C12—C11	120.55 (18)
C3—C4—C5	117.13 (17)	C13—C12—H12	119.7
C3—C4—C7	121.17 (17)	C11—C12—H12	119.7
C5—C4—C7	121.71 (17)	C14—C13—C12	119.93 (19)
C4—C5—C6	122.13 (18)	C14—C13—H13	120.0
C4—C5—H5	118.9	C12—C13—H13	120.0
C6—C5—H5	118.9	C15—C14—C13	119.65 (18)
C1—C6—C5	119.08 (17)	C15—C14—H14	120.2
C1—C6—H6	120.5	C13—C14—H14	120.2
C5—C6—H6	120.5	C14—C15—C16	120.78 (19)
C4—C7—H7A	109.5	C14—C15—H15	119.6
C4—C7—H7B	109.5	C16—C15—H15	119.6
H7A—C7—H7B	109.5	C15—C16—C11	120.30 (18)
C4—C7—H7C	109.5	C15—C16—H16	119.8
H7A—C7—H7C	109.5	C11—C16—H16	119.8
H7B—C7—H7C	109.5
C8—N1—N2—C9	−0.07 (19)	C9—N3—C8—O1	178.18 (18)
C1—N1—N2—C9	179.13 (15)	C10—N3—C8—O1	2.4 (3)
C8—N1—C1—C2	172.54 (16)	C9—N3—C8—N1	−0.95 (18)
N2—N1—C1—C2	−6.5 (2)	C10—N3—C8—N1	−176.71 (14)
C8—N1—C1—C6	−7.7 (3)	N1—N2—C9—N3	−0.6 (2)
N2—N1—C1—C6	173.26 (15)	C8—N3—C9—N2	1.0 (2)
C6—C1—C2—C3	0.1 (3)	C10—N3—C9—N2	176.61 (16)
N1—C1—C2—C3	179.85 (15)	C9—N3—C10—C11	−75.1 (2)
C1—C2—C3—C4	0.5 (3)	C8—N3—C10—C11	99.78 (19)
C2—C3—C4—C5	−0.5 (3)	N3—C10—C11—C12	−80.5 (2)
C2—C3—C4—C7	179.72 (15)	N3—C10—C11—C16	98.3 (2)
C3—C4—C5—C6	−0.1 (3)	C16—C11—C12—C13	−0.1 (3)
C7—C4—C5—C6	179.67 (16)	C10—C11—C12—C13	178.78 (17)
C2—C1—C6—C5	−0.7 (3)	C11—C12—C13—C14	0.7 (3)
N1—C1—C6—C5	179.57 (15)	C12—C13—C14—C15	−0.9 (3)
C4—C5—C6—C1	0.7 (3)	C13—C14—C15—C16	0.4 (3)
N2—N1—C8—O1	−178.45 (17)	C14—C15—C16—C11	0.3 (3)
C1—N1—C8—O1	2.4 (3)	C12—C11—C16—C15	−0.4 (3)
N2—N1—C8—N3	0.64 (18)	C10—C11—C16—C15	−179.28 (17)
C1—N1—C8—N3	−178.46 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.19	3.114 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.19	3.114 (2)	174

Symmetry code: (i) .