3-({4-[(2-Methyl­benzyl­idene)amino]-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl}meth­yl)-1,3-benzoxazol-2(3H)-one

Aydın, A.; Hekimoğlu, N.; Akkurt, M.; Önkol, T.; Çiçekli, Ş.U.; Büyükgüngör, O.

doi:10.1107/S1600536812051458

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o169-o170

doi:10.1107/S1600536812051458

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3-({4-[(2-Methylbenzylidene)amino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)-1,3-benzoxazol-2(3H)-one

Abdullah Aydın,^a ^* Nuray Hekimoğlu,^b Mehmet Akkurt,^c Tijen Önkol,^d Şölen Urlu Çiçekli ^d and Orhan Büyükgüngör ^e

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Physics, Institute of Science and Technology, Kastamonu University, 37100 Kastamonu, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and ^eDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

(Received 14 December 2012; accepted 20 December 2012; online 4 January 2013)

In the title compound, C₁₈H₁₅N₅O₂S, a weak intramolecular C—H⋯S hydrogen bond results in a small dihedral angle of 3.71 (9)° between the methylphenyl 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 molecules into chains along [001], and weak C—H⋯N hydrogen bonds and π–π interactions 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_r = 365.42
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.110
S = 1.03
3958 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812051458/cv5375sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812051458/cv5375Isup3.cml

checkCIF report

Comment top

In continuation of our studies of hybrid molecules containing 2(3H)- benzoxazolone fragment (Aydın et al., 2005), herewith we present the title compound, (I). In (I) (Fig. 1), the 2,3-dihydro-1,3-benzoxazole ring (N1/O1/C1—C7) is essentially planar with the maximum deviation of the C7 atom from the mean plane of -0.034 (2) Å. This ring system makes dihedral angles of 77.32 (8) and 80.09 (8)°, with the 4,5-dihydro-1H-1,2,4-triazole ring (N2–N4/C9/C10) and the benzene ring (C12–C17), respectively. The dihedral angle between the 4,5-dihydro-1H-1,2,4-triazole ring and the benzene ring is 3.71 (9)°. All bond lengths and angles are comparable with those observed in similar compounds (Aydın et al., 2005; 2012).

In the crystal, neighbouring molecules are linked by N—H···O and C—H···N hydrogen bonding interactions, forming a two dimensional network parallel to the (101) plane (Table 1, Fig. 2). In addition, the crystal packing is stabilized by a weak C—H···π interaction and two π-π stacking interactions [Cg1···Cg3(1 - x, -y, -z) = 3.5074 (11) Å and Cg2···Cg4(x, -1 + y,z) = 3.6160 (10) Å; where Cg1, Cg2, Cg3 and Cg4 are the centroids of the O1/C1/C6/N1/C7, N2/C9/N4/N3/C10, C1–C6 and C12–C17 rings, respectively].

Molecular orbital calculations using semi-empirical (AM1) have been carried out for the title compound with MOPAC (Dewar et al., 1985; Stewart, 1993). The values of the structural parameters of the title compound obtained by the results of the theoretical calculations (based on isolated molecules) and X-ray structural determinations in the solid state are almost identical within experimental error. The calculated dipole moment of (I) is 3.243 D. The HOMO and LUMO energy levels are -8.65563 and -.31527 eV, respectively.

Related literature top

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 top

To a suspension of o-methylbenzaldehyde (0.0022 mol) in glacial acetic acid (3 ml), 0.002 mol [(4-amino-5-sulfanylidene-1,2,4-triazol-3-yl) methyl]-2(3H)-benzoxazolone was added. The reaction mixture was placed in microwave oven and irradiated for minutes changing between 15–30 min at 398 K (300 W). After completion of the reaction by monitoring with TLC, the reaction mixture was kept overnight at room temperature. The precipitate was collected by filtration, washed with water, dried, and crystallized from EtOH-acetone.

Yield, 58%, m.p.: 494–495 K. IR v_max cm^-1, 3186, 1772, 1484, 1268. ¹H-NMR (DMSO-d₆) δ 14.16 (1H, s, NH), 10.28 (1H, s, =CH), 7.84 (1H, d, Ar—H), 7.39 (1H, t, Ar—H), 7.29–7.18 (4H, m, Ar—H, H7, H4), 7.12 (1H, t, H6), 7.06 (1H, t, H5), 5.21 (2H, s, CH₂), 2.40 (3H, s, CH₃). Elemental analysis: C₁₈H₁₅N₅O₂S, Calc.(%) / Found (%): C:59.16/59.38, H: 4.14/3.95, N: 19.17/19.15. (Urlu-Cicekli et al., 2012).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecule shown with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding of the title compound viewed down the b axis. H atoms not involved in hydrogen bondings are omitted for the sake of clarity.

3-({4-[(2-Methylbenzylidene)amino]-5-sulfanylidene-1H- 1,2,4-triazol-3-yl}methyl)-1,3-benzoxazol-2(3H)-one top

Crystal data top

C₁₈H₁₅N₅O₂S	F(000) = 760
M_r = 365.42	D_x = 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

Data collection top

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	R_int = 0.029
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scans	h = −23→23
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
T_min = 0.881, T_max = 0.955	l = −19→11
10084 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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0522P)² + 0.2998P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3958 reflections	Δρ_max = 0.21 e Å⁻³
237 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₅N₅O₂S	V = 1743.4 (2) Å³
M_r = 365.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.0823 (13) Å	µ = 0.21 mm⁻¹
b = 6.4623 (4) Å	T = 296 K
c = 15.1892 (11) Å	0.62 × 0.48 × 0.22 mm
β = 100.821 (6)°

Data collection top

Stoe IPDS 2 diffractometer	3958 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3034 reflections with I > 2σ(I)
T_min = 0.881, T_max = 0.955	R_int = 0.029
10084 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
3958 reflections	Δρ_min = −0.27 e Å⁻³
237 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₅O₂S
M_r	365.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.0823 (13), 6.4623 (4), 15.1892 (11)
β (°)	100.821 (6)
V (Å³)	1743.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.62 × 0.48 × 0.22

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.881, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	10084, 3958, 3034
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.110, 1.03
No. of reflections	3958
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Aydın, A., Önkol, T., Akkurt, M. & Büyükgüngör, O. (2005). Anal. Sci. 21, x119–x120. Google Scholar
Aydın, A., Soyer, Z., Akkurt, M. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1544–o1545. CSD CrossRef IUCr Journals Google Scholar
Dewar, M. J. S., Zoebish, E. G., Healy, E. F. & Stewart, J. J. P. (1985). J. Am. Chem. Soc. 107, 3902–3909. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stewart, J. J. P. (1993). MOPAC7.0. QCPE Program No. 455. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN, USA. Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Urlu-Cicekli, S., Onkol, T., Ozgen, S. & Sahin, M. F. (2012). Rev. Roum. Chim. 57, 187–195. CAS Google Scholar

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Volume 69| Part 2| February 2013| Pages o169-o170

doi:10.1107/S1600536812051458

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

3-({4-[(2-Methyl­benzyl­­idene)amino]-5-sulfanyl­­idene-1H-1,2,4-triazol-3-yl}meth­yl)-1,3-benzoxazol-2(3H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-({4-[(2-Methylbenzylidene)amino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)-1,3-benzoxazol-2(3H)-one