3-({4-[(2-Methyl-benzyl-idene)amino]-5-sulfanyl-idene-1H-1,2,4-triazol-3-yl}meth-yl)-1,3-benzoxazol-2(3H)-one.

In the title compound, C(18)H(15)N(5)O(2)S, a weak intra-molecular C-H⋯S hydrogen bond results in a small dihedral angle of 3.71 (9)° between the methyl-phenyl and triazole rings, which, in turn, form dihedral angles of 80.09 (8) and 77.32 (8)°, respectively, with the benzoxazolone mean plane. In the crystal, N-H⋯O hydrogen bonds link mol-ecules into chains along [001], and weak C-H⋯N hydrogen bonds and π-π inter-actions between the five- and six-membered rings [centroid-centroid distances = 3.5074 (11) and 3.616 (1) Å] consolidate the crystal packing.

Related literature

For details of the synthesis, see: Urlu-Cicekli et al. (2012 ▶). For related structures, see: Aydın et al. (2005 ▶, 2012 ▶). For a MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985 ▶); Stewart (1993 ▶).

Experimental

Crystal data

C18H15N5O2S

M = 365.42

Monoclinic,

a = 18.0823 (13) Å

b = 6.4623 (4) Å

c = 15.1892 (11) Å

β = 100.821 (6)°

V = 1743.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.62 × 0.48 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.881, T max = 0.955

10084 measured reflections

3958 independent reflections

3034 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.03

3958 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051458/cv5375sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051458/cv5375Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051458/cv5375Isup3.cml

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

C18H15N5O2S	F(000) = 760
Mr = 365.42	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14230 reflections
a = 18.0823 (13) Å	θ = 1.6–28.1°
b = 6.4623 (4) Å	µ = 0.21 mm−1
c = 15.1892 (11) Å	T = 296 K
β = 100.821 (6)°	Prism, colourless
V = 1743.4 (2) Å3	0.62 × 0.48 × 0.22 mm
Z = 4

Stoe IPDS 2 diffractometer	3958 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3034 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.029
Detector resolution: 6.67 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scans	h = −23→23
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.881, Tmax = 0.955	l = −19→11
10084 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.2998P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3958 reflections	Δρmax = 0.21 e Å−3
237 parameters	Δρmin = −0.27 e Å−3
0 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: 0.0052 (11)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.82101 (3)	0.21261 (9)	0.49178 (3)	0.0661 (2)
O1	0.57137 (8)	−0.3003 (2)	0.04586 (9)	0.0678 (5)
O2	0.69462 (8)	−0.2533 (3)	0.04013 (11)	0.0879 (6)
N1	0.63001 (7)	−0.0347 (2)	0.11876 (9)	0.0488 (4)
N2	0.76393 (7)	0.19558 (19)	0.30855 (8)	0.0395 (4)
N3	0.73011 (8)	−0.0492 (2)	0.38509 (9)	0.0502 (4)
N4	0.69353 (8)	−0.0842 (2)	0.29879 (9)	0.0506 (4)
N5	0.78893 (7)	0.3744 (2)	0.27189 (9)	0.0461 (4)
C1	0.51976 (10)	−0.1911 (3)	0.08396 (12)	0.0528 (5)
C2	0.44430 (11)	−0.2291 (3)	0.07683 (16)	0.0697 (7)
C3	0.40518 (11)	−0.0913 (4)	0.11896 (16)	0.0753 (8)
C4	0.43962 (11)	0.0728 (4)	0.16624 (15)	0.0715 (7)
C5	0.51655 (10)	0.1116 (3)	0.17325 (13)	0.0599 (6)
C6	0.55532 (9)	−0.0251 (3)	0.13032 (10)	0.0456 (5)
C7	0.63901 (11)	−0.1995 (3)	0.06662 (12)	0.0596 (6)
C8	0.69017 (9)	0.1059 (3)	0.15606 (11)	0.0529 (5)
C9	0.71518 (8)	0.0672 (2)	0.25402 (10)	0.0420 (4)
C10	0.77295 (8)	0.1213 (2)	0.39537 (10)	0.0434 (4)
C11	0.84178 (9)	0.4744 (3)	0.31801 (11)	0.0505 (5)
C12	0.87066 (8)	0.6636 (2)	0.28379 (11)	0.0449 (5)
C13	0.85106 (10)	0.7124 (3)	0.19330 (12)	0.0565 (6)
C14	0.87728 (12)	0.8909 (3)	0.16082 (15)	0.0698 (8)
C15	0.92305 (12)	1.0222 (3)	0.21815 (18)	0.0753 (9)
C16	0.94356 (11)	0.9736 (3)	0.30694 (17)	0.0674 (8)
C17	0.91832 (9)	0.7942 (3)	0.34227 (13)	0.0529 (6)
C18	0.94257 (14)	0.7470 (4)	0.44018 (16)	0.0802 (8)
H2	0.42100	−0.34200	0.04520	0.0840*
H3	0.35370	−0.11010	0.11530	0.0900*
H3A	0.72590	−0.12990	0.42890	0.0600*
H4	0.41110	0.16160	0.19460	0.0860*
H5	0.54000	0.22390	0.20530	0.0720*
H8A	0.67270	0.24760	0.14660	0.0630*
H8B	0.73230	0.08710	0.12570	0.0630*
H11	0.86300	0.42740	0.37500	0.0610*
H13	0.82000	0.62380	0.15460	0.0680*
H14	0.86410	0.92290	0.10020	0.0840*
H15	0.94010	1.14430	0.19640	0.0900*
H16	0.97520	1.06280	0.34470	0.0810*
H18A	0.98610	0.82820	0.46430	0.1200*
H18B	0.95470	0.60270	0.44770	0.1200*
H18C	0.90240	0.77980	0.47110	0.1200*

	U11	U22	U33	U12	U13	U23
S1	0.0839 (4)	0.0758 (3)	0.0346 (2)	−0.0221 (3)	0.0009 (2)	−0.0032 (2)
O1	0.0728 (8)	0.0642 (8)	0.0609 (8)	0.0012 (7)	−0.0013 (6)	−0.0295 (7)
O2	0.0712 (9)	0.1311 (14)	0.0591 (9)	0.0311 (9)	0.0062 (7)	−0.0369 (9)
N1	0.0457 (7)	0.0603 (8)	0.0389 (7)	−0.0010 (6)	0.0039 (5)	−0.0145 (6)
N2	0.0417 (6)	0.0436 (7)	0.0328 (6)	−0.0067 (5)	0.0059 (5)	−0.0014 (5)
N3	0.0569 (8)	0.0546 (8)	0.0386 (7)	−0.0128 (6)	0.0074 (6)	0.0046 (6)
N4	0.0523 (7)	0.0565 (8)	0.0421 (7)	−0.0142 (6)	0.0068 (6)	−0.0025 (6)
N5	0.0530 (7)	0.0443 (7)	0.0399 (7)	−0.0085 (6)	0.0057 (5)	0.0031 (6)
C1	0.0567 (10)	0.0530 (9)	0.0448 (9)	−0.0032 (8)	−0.0005 (7)	−0.0062 (7)
C2	0.0622 (11)	0.0728 (13)	0.0676 (13)	−0.0179 (10)	−0.0044 (9)	0.0032 (10)
C3	0.0509 (10)	0.1009 (17)	0.0711 (14)	−0.0056 (11)	0.0034 (9)	0.0198 (12)
C4	0.0624 (11)	0.0892 (15)	0.0650 (12)	0.0249 (11)	0.0177 (9)	0.0078 (11)
C5	0.0604 (10)	0.0635 (11)	0.0539 (10)	0.0106 (9)	0.0057 (8)	−0.0113 (9)
C6	0.0461 (8)	0.0506 (9)	0.0375 (8)	0.0030 (7)	0.0011 (6)	−0.0051 (6)
C7	0.0599 (10)	0.0753 (12)	0.0400 (9)	0.0120 (9)	−0.0002 (7)	−0.0175 (8)
C8	0.0508 (9)	0.0694 (11)	0.0367 (8)	−0.0118 (8)	0.0036 (6)	−0.0021 (7)
C9	0.0391 (7)	0.0498 (8)	0.0368 (7)	−0.0060 (6)	0.0067 (6)	−0.0036 (6)
C10	0.0455 (8)	0.0486 (8)	0.0363 (7)	−0.0028 (7)	0.0081 (6)	0.0003 (6)
C11	0.0533 (9)	0.0509 (9)	0.0434 (8)	−0.0082 (7)	−0.0010 (7)	0.0060 (7)
C12	0.0433 (8)	0.0419 (8)	0.0495 (9)	−0.0003 (6)	0.0086 (6)	0.0042 (6)
C13	0.0614 (10)	0.0560 (10)	0.0519 (10)	−0.0004 (8)	0.0105 (8)	0.0082 (8)
C14	0.0835 (14)	0.0639 (12)	0.0674 (13)	0.0069 (11)	0.0281 (10)	0.0218 (10)
C15	0.0765 (13)	0.0500 (11)	0.1094 (19)	−0.0025 (10)	0.0431 (13)	0.0200 (12)
C16	0.0590 (11)	0.0476 (10)	0.0968 (17)	−0.0087 (8)	0.0175 (10)	−0.0044 (10)
C17	0.0477 (9)	0.0457 (9)	0.0638 (11)	−0.0027 (7)	0.0066 (7)	−0.0027 (8)
C18	0.0886 (15)	0.0728 (14)	0.0678 (14)	−0.0154 (12)	−0.0146 (11)	−0.0060 (11)

S1—C10	1.6643 (15)	C11—C12	1.463 (2)
O1—C1	1.381 (2)	C12—C17	1.399 (2)
O1—C7	1.369 (2)	C12—C13	1.390 (2)
O2—C7	1.202 (3)	C13—C14	1.374 (3)
N1—C6	1.396 (2)	C14—C15	1.376 (3)
N1—C7	1.355 (2)	C15—C16	1.367 (4)
N1—C8	1.449 (2)	C16—C17	1.390 (3)
N2—N5	1.3944 (18)	C17—C18	1.501 (3)
N2—C9	1.3701 (19)	C2—H2	0.9300
N2—C10	1.3839 (19)	C3—H3	0.9300
N3—N4	1.3716 (19)	C4—H4	0.9300
N3—C10	1.3391 (19)	C5—H5	0.9300
N4—C9	1.2934 (19)	C8—H8A	0.9700
N5—C11	1.253 (2)	C8—H8B	0.9700
N3—H3A	0.8600	C11—H11	0.9300
C1—C6	1.375 (3)	C13—H13	0.9300
C1—C2	1.371 (3)	C14—H14	0.9300
C2—C3	1.369 (3)	C15—H15	0.9300
C3—C4	1.364 (3)	C16—H16	0.9300
C4—C5	1.398 (3)	C18—H18A	0.9600
C5—C6	1.367 (3)	C18—H18B	0.9600
C8—C9	1.493 (2)	C18—H18C	0.9600
C1—O1—C7	107.77 (14)	C12—C13—C14	120.31 (17)
C6—N1—C7	109.49 (14)	C13—C14—C15	119.9 (2)
C6—N1—C8	126.61 (14)	C14—C15—C16	120.17 (19)
C7—N1—C8	123.90 (14)	C15—C16—C17	121.7 (2)
N5—N2—C9	118.71 (12)	C16—C17—C18	119.74 (19)
N5—N2—C10	132.76 (12)	C12—C17—C16	117.77 (18)
C9—N2—C10	108.26 (12)	C12—C17—C18	122.50 (18)
N4—N3—C10	114.32 (13)	C1—C2—H2	122.00
N3—N4—C9	103.80 (13)	C3—C2—H2	122.00
N2—N5—C11	118.33 (14)	C2—C3—H3	119.00
N4—N3—H3A	123.00	C4—C3—H3	119.00
C10—N3—H3A	123.00	C3—C4—H4	119.00
C2—C1—C6	122.91 (18)	C5—C4—H4	119.00
O1—C1—C6	109.00 (15)	C4—C5—H5	122.00
O1—C1—C2	128.06 (18)	C6—C5—H5	122.00
C1—C2—C3	116.16 (19)	N1—C8—H8A	110.00
C2—C3—C4	121.81 (19)	N1—C8—H8B	110.00
C3—C4—C5	121.9 (2)	C9—C8—H8A	110.00
C4—C5—C6	116.10 (18)	C9—C8—H8B	110.00
N1—C6—C5	133.14 (17)	H8A—C8—H8B	108.00
N1—C6—C1	105.75 (15)	N5—C11—H11	119.00
C1—C6—C5	121.07 (16)	C12—C11—H11	119.00
O1—C7—N1	107.96 (16)	C12—C13—H13	120.00
O2—C7—N1	128.50 (19)	C14—C13—H13	120.00
O1—C7—O2	123.53 (18)	C13—C14—H14	120.00
N1—C8—C9	110.46 (14)	C15—C14—H14	120.00
N2—C9—C8	122.77 (13)	C14—C15—H15	120.00
N2—C9—N4	111.35 (13)	C16—C15—H15	120.00
N4—C9—C8	125.86 (14)	C15—C16—H16	119.00
N2—C10—N3	102.25 (12)	C17—C16—H16	119.00
S1—C10—N3	126.12 (12)	C17—C18—H18A	109.00
S1—C10—N2	131.61 (11)	C17—C18—H18B	109.00
N5—C11—C12	121.20 (15)	C17—C18—H18C	109.00
C13—C12—C17	120.23 (15)	H18A—C18—H18B	109.00
C11—C12—C13	119.96 (14)	H18A—C18—H18C	110.00
C11—C12—C17	119.81 (15)	H18B—C18—H18C	109.00
C7—O1—C1—C2	176.4 (2)	N3—N4—C9—N2	0.12 (17)
C7—O1—C1—C6	−1.5 (2)	N2—N5—C11—C12	−179.86 (14)
C1—O1—C7—O2	−177.25 (19)	C2—C1—C6—C5	0.7 (3)
C1—O1—C7—N1	1.76 (19)	C2—C1—C6—N1	−177.42 (18)
C7—N1—C6—C1	0.53 (19)	O1—C1—C2—C3	−177.6 (2)
C8—N1—C6—C1	−179.11 (15)	C6—C1—C2—C3	−0.1 (3)
C6—N1—C7—O1	−1.43 (19)	O1—C1—C6—N1	0.57 (19)
C8—N1—C7—O2	−2.8 (3)	O1—C1—C6—C5	178.73 (16)
C8—N1—C7—O1	178.22 (14)	C1—C2—C3—C4	−0.8 (3)
C6—N1—C7—O2	177.5 (2)	C2—C3—C4—C5	1.0 (4)
C8—N1—C6—C5	3.1 (3)	C3—C4—C5—C6	−0.3 (3)
C6—N1—C8—C9	74.0 (2)	C4—C5—C6—C1	−0.5 (3)
C7—N1—C8—C9	−105.58 (18)	C4—C5—C6—N1	177.04 (19)
C7—N1—C6—C5	−177.31 (19)	N1—C8—C9—N4	7.5 (2)
C9—N2—N5—C11	−169.40 (15)	N1—C8—C9—N2	−170.82 (13)
C9—N2—C10—S1	−176.79 (12)	N5—C11—C12—C13	−13.5 (2)
N5—N2—C10—S1	−3.0 (3)	N5—C11—C12—C17	166.92 (16)
C10—N2—C9—C8	177.50 (14)	C11—C12—C13—C14	179.29 (17)
N5—N2—C9—N4	−175.91 (13)	C17—C12—C13—C14	−1.1 (3)
C10—N2—N5—C11	17.3 (2)	C11—C12—C17—C16	−179.17 (16)
C9—N2—C10—N3	1.52 (15)	C11—C12—C17—C18	0.9 (3)
C10—N2—C9—N4	−1.08 (17)	C13—C12—C17—C16	1.2 (2)
N5—N2—C10—N3	175.34 (15)	C13—C12—C17—C18	−178.74 (18)
N5—N2—C9—C8	2.7 (2)	C12—C13—C14—C15	−0.1 (3)
C10—N3—N4—C9	0.95 (18)	C13—C14—C15—C16	1.2 (3)
N4—N3—C10—N2	−1.55 (17)	C14—C15—C16—C17	−1.1 (3)
N4—N3—C10—S1	176.89 (11)	C15—C16—C17—C12	−0.2 (3)
N3—N4—C9—C8	−178.40 (15)	C15—C16—C17—C18	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.86	2.03	2.856 (2)	162
C4—H4···N4ii	0.93	2.52	3.387 (3)	155
C8—H8B···O2	0.97	2.58	2.924 (3)	101
C11—H11···S1	0.93	2.48	3.2159 (18)	136
C3—H3···Cg2iii	0.93	2.94	3.635 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.86	2.03	2.856 (2)	162
C4—H4⋯N4ii	0.93	2.52	3.387 (3)	155
C11—H11⋯S1	0.93	2.48	3.2159 (18)	136

Symmetry codes: (i) ; (ii) .