3-[(5-Methyl-2-oxo-1,3-benzoxazol-3-yl)meth­yl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C₁₇H₁₄N₄O₂S, the dihedral angle between the triazole ring and the benzoxazoline ring system is 88.20 (4)°, showing that these rings are almost perpendicular to each other. The crystal structure is stabilized by inter­molecular N—H...O inter­actions, linking the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The structure of the title compound, (I) (Fig. 1), differs from that reported for 3-[(5-methyl-2-benzoxazolinone-3-yl)methyl] -4-allyl-1H-1,2,4-triazole-5(4H)-thione, (II) (Köysal et al., 2007).

The dihedral angle between the triazole ring and the benzoxazoline ring system is 88.20 (4)°, showing that these ring systems are almost perpendicular to each other. Both compounds (I) and (II) exhibit weak but slightly different intermolecular interactions. In (I), there is an N—H···O interaction, while in (II), the interactions are N—H···S, C—H···S and π–π.

Related literature

The title compound is a similar isomorph of 3-[(5-methyl-2-benzoxazolinone-3-yl)methyl]-4-allyl-1H-1,2,4- triazole-5(4H)-thione (Köysal et al., 2007). The molecular geometry of the title compound is in agreement with values in our related structures (Köysal et al., 2003, 2007).

S2. Experimental

The title compound was synthesized using the same procedure as in our previous paper (Köysal et al., 2007).

S3. Refinement

H atoms were located geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H, 0.97Å for CH₂ and 0.96 Å for methyl H.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures

	Fig. 1. The structure of compound (I). showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the intermolecular N—H···O interactions (dashed lines) between the molecules of (I), down the a axis.

3-[(5-Methyl-2-oxo-1,3-benzoxazol-3-yl)methyl]-4-phenyl-1H- 1,2,4-triazole-5(4H)-thione

Crystal data

C17H14N4O2S	F(000) = 704
Mr = 338.38	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21935 reflections
a = 12.2347 (6) Å	θ = 2.4–28.0°
b = 12.8379 (7) Å	µ = 0.22 mm^−1
c = 11.0797 (6) Å	T = 293 K
β = 112.531 (4)°	Prism, colourless
V = 1607.43 (15) Å^3	0.54 × 0.39 × 0.24 mm
Z = 4

Data collection

Stoe IPDS II diffractometer	3150 independent reflections
Radiation source: fine-focus sealed tube	2436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.4°
ω scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.484, Tmax = 0.849	l = −13→13
20943 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.0405P] where P = (Fo^2 + 2Fc^2)/3
3150 reflections	(Δ/σ)max = 0.002
222 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.92413 (16)	0.44503 (12)	0.32666 (15)	0.0450 (4)
C2	1.02318 (16)	0.39451 (13)	0.40705 (17)	0.0495 (4)
H2	1.0952	0.4001	0.3974	0.059*
C3	1.00960 (17)	0.33420 (13)	0.50425 (17)	0.0512 (4)
H3	1.0744	0.2969	0.5601	0.061*
C4	0.90390 (16)	0.32719 (13)	0.52166 (17)	0.0505 (4)
C5	0.80410 (16)	0.38007 (13)	0.43740 (16)	0.0480 (4)
H5	0.7319	0.3761	0.4470	0.058*
C6	0.81727 (15)	0.43839 (12)	0.33947 (15)	0.0434 (4)
C7	0.8973 (2)	0.26370 (18)	0.6325 (2)	0.0726 (6)
H7A	0.9207	0.1933	0.6255	0.109*
H7B	0.8177	0.2643	0.6289	0.109*
H7C	0.9494	0.2929	0.7141	0.109*
C8	0.79970 (19)	0.54601 (15)	0.17374 (18)	0.0587 (5)
C9	0.61703 (16)	0.52145 (14)	0.21542 (17)	0.0535 (4)
H9A	0.5796	0.4582	0.2284	0.064*
H9B	0.5767	0.5430	0.1252	0.064*
C10	0.60490 (15)	0.60493 (12)	0.30378 (16)	0.0465 (4)
C11	0.52524 (16)	0.71128 (12)	0.40576 (17)	0.0483 (4)
C12	0.39529 (16)	0.56646 (13)	0.27743 (16)	0.0471 (4)
C13	0.3941 (2)	0.46557 (14)	0.31950 (19)	0.0606 (5)
H13	0.4625	0.4353	0.3792	0.073*
C14	0.2889 (2)	0.41019 (17)	0.2710 (2)	0.0742 (6)
H14	0.2868	0.3416	0.2969	0.089*
C15	0.1879 (2)	0.4560 (2)	0.1850 (2)	0.0777 (7)
H15	0.1174	0.4187	0.1534	0.093*
C16	0.1908 (2)	0.5569 (2)	0.1453 (2)	0.0775 (6)
H16	0.1219	0.5879	0.0875	0.093*
C17	0.29451 (18)	0.61215 (16)	0.19043 (19)	0.0612 (5)
H17	0.2966	0.6801	0.1623	0.073*
N1	0.73919 (13)	0.50064 (11)	0.24030 (13)	0.0497 (3)
N2	0.50386 (12)	0.62461 (10)	0.32577 (13)	0.0450 (3)
N3	0.63611 (14)	0.73594 (12)	0.42496 (16)	0.0541 (4)
N4	0.68742 (14)	0.67115 (12)	0.36309 (15)	0.0540 (4)
O1	0.91324 (12)	0.51094 (10)	0.22290 (12)	0.0577 (3)
O2	0.76463 (17)	0.60708 (14)	0.08433 (16)	0.0892 (5)
S1	0.43585 (5)	0.76920 (4)	0.46729 (5)	0.06125 (17)
H3A	0.678 (2)	0.7849 (18)	0.475 (2)	0.064 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0550 (10)	0.0402 (8)	0.0446 (8)	0.0023 (7)	0.0246 (7)	−0.0024 (6)
C2	0.0462 (10)	0.0515 (9)	0.0545 (9)	0.0042 (7)	0.0234 (8)	−0.0051 (7)
C3	0.0482 (10)	0.0496 (9)	0.0508 (9)	0.0072 (7)	0.0136 (7)	0.0001 (7)
C4	0.0541 (11)	0.0461 (9)	0.0506 (9)	0.0016 (7)	0.0191 (8)	0.0031 (7)
C5	0.0468 (10)	0.0442 (8)	0.0557 (9)	−0.0012 (7)	0.0226 (7)	0.0012 (7)
C6	0.0473 (10)	0.0369 (7)	0.0441 (8)	0.0052 (6)	0.0156 (7)	−0.0035 (6)
C7	0.0757 (15)	0.0754 (13)	0.0699 (13)	0.0115 (11)	0.0315 (11)	0.0253 (11)
C8	0.0747 (14)	0.0557 (10)	0.0527 (10)	0.0202 (9)	0.0321 (9)	0.0085 (8)
C9	0.0503 (11)	0.0523 (10)	0.0517 (9)	0.0110 (8)	0.0129 (8)	−0.0056 (8)
C10	0.0450 (10)	0.0432 (8)	0.0491 (9)	0.0077 (7)	0.0156 (7)	0.0016 (7)
C11	0.0529 (11)	0.0389 (8)	0.0539 (9)	0.0010 (7)	0.0213 (8)	−0.0007 (7)
C12	0.0510 (11)	0.0435 (8)	0.0505 (9)	−0.0031 (7)	0.0234 (8)	−0.0043 (7)
C13	0.0740 (14)	0.0496 (10)	0.0611 (11)	−0.0045 (9)	0.0291 (10)	0.0014 (8)
C14	0.1024 (19)	0.0557 (11)	0.0797 (14)	−0.0269 (12)	0.0518 (14)	−0.0117 (10)
C15	0.0731 (16)	0.0910 (17)	0.0760 (14)	−0.0338 (13)	0.0364 (12)	−0.0251 (12)
C16	0.0526 (13)	0.0966 (17)	0.0763 (14)	−0.0113 (11)	0.0167 (10)	−0.0112 (12)
C17	0.0531 (12)	0.0587 (11)	0.0678 (12)	−0.0005 (9)	0.0187 (9)	0.0017 (9)
N1	0.0524 (9)	0.0478 (7)	0.0493 (7)	0.0130 (6)	0.0201 (6)	0.0032 (6)
N2	0.0444 (8)	0.0393 (7)	0.0506 (7)	0.0017 (6)	0.0174 (6)	−0.0012 (5)
N3	0.0494 (9)	0.0474 (8)	0.0661 (9)	−0.0049 (7)	0.0228 (7)	−0.0132 (7)
N4	0.0461 (9)	0.0528 (8)	0.0628 (9)	0.0018 (6)	0.0204 (7)	−0.0095 (7)
O1	0.0681 (9)	0.0596 (7)	0.0556 (7)	0.0148 (6)	0.0352 (6)	0.0106 (6)
O2	0.1090 (14)	0.0961 (11)	0.0760 (10)	0.0471 (10)	0.0503 (9)	0.0423 (9)
S1	0.0609 (3)	0.0541 (3)	0.0784 (3)	−0.0008 (2)	0.0374 (3)	−0.0130 (2)

Geometric parameters (Å, º)

C1—C2	1.362 (2)	C9—H9B	0.9700
C1—C6	1.371 (2)	C10—N4	1.290 (2)
C1—O1	1.3922 (19)	C10—N2	1.372 (2)
C2—C3	1.387 (3)	C11—N3	1.328 (2)
C2—H2	0.9300	C11—N2	1.384 (2)
C3—C4	1.382 (3)	C11—S1	1.6689 (18)
C3—H3	0.9300	C12—C17	1.372 (3)
C4—C5	1.396 (2)	C12—C13	1.379 (2)
C4—C7	1.502 (3)	C12—N2	1.436 (2)
C5—C6	1.378 (2)	C13—C14	1.386 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—N1	1.398 (2)	C14—C15	1.371 (4)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—C16	1.371 (4)
C7—H7C	0.9600	C15—H15	0.9300
C8—O2	1.206 (2)	C16—C17	1.371 (3)
C8—O1	1.360 (2)	C16—H16	0.9300
C8—N1	1.360 (2)	C17—H17	0.9300
C9—N1	1.437 (2)	N3—N4	1.373 (2)
C9—C10	1.497 (2)	N3—H3A	0.86 (2)
C9—H9A	0.9700
C2—C1—C6	123.21 (15)	N4—C10—C9	123.39 (17)
C2—C1—O1	127.52 (15)	N2—C10—C9	124.74 (15)
C6—C1—O1	109.27 (14)	N3—C11—N2	103.01 (14)
C1—C2—C3	115.61 (16)	N3—C11—S1	128.11 (14)
C1—C2—H2	122.2	N2—C11—S1	128.85 (14)
C3—C2—H2	122.2	C17—C12—C13	121.08 (18)
C4—C3—C2	122.81 (16)	C17—C12—N2	119.57 (16)
C4—C3—H3	118.6	C13—C12—N2	119.35 (17)
C2—C3—H3	118.6	C12—C13—C14	118.6 (2)
C3—C4—C5	120.03 (16)	C12—C13—H13	120.7
C3—C4—C7	119.74 (17)	C14—C13—H13	120.7
C5—C4—C7	120.23 (17)	C15—C14—C13	120.3 (2)
C6—C5—C4	117.04 (16)	C15—C14—H14	119.8
C6—C5—H5	121.5	C13—C14—H14	119.8
C4—C5—H5	121.5	C14—C15—C16	120.1 (2)
C1—C6—C5	121.29 (15)	C14—C15—H15	120.0
C1—C6—N1	105.95 (14)	C16—C15—H15	120.0
C5—C6—N1	132.75 (16)	C17—C16—C15	120.4 (2)
C4—C7—H7A	109.5	C17—C16—H16	119.8
C4—C7—H7B	109.5	C15—C16—H16	119.8
H7A—C7—H7B	109.5	C16—C17—C12	119.5 (2)
C4—C7—H7C	109.5	C16—C17—H17	120.3
H7A—C7—H7C	109.5	C12—C17—H17	120.3
H7B—C7—H7C	109.5	C8—N1—C6	108.72 (15)
O2—C8—O1	122.11 (19)	C8—N1—C9	123.96 (15)
O2—C8—N1	128.9 (2)	C6—N1—C9	127.18 (15)
O1—C8—N1	109.02 (14)	C10—N2—C11	107.44 (14)
N1—C9—C10	111.35 (15)	C10—N2—C12	127.27 (13)
N1—C9—H9A	109.4	C11—N2—C12	125.28 (14)
C10—C9—H9A	109.4	C11—N3—N4	114.19 (15)
N1—C9—H9B	109.4	C11—N3—H3A	126.6 (15)
C10—C9—H9B	109.4	N4—N3—H3A	119.1 (15)
H9A—C9—H9B	108.0	C10—N4—N3	103.60 (15)
N4—C10—N2	111.76 (14)	C8—O1—C1	106.97 (13)
C6—C1—C2—C3	0.4 (2)	C1—C6—N1—C8	−2.22 (18)
O1—C1—C2—C3	179.27 (15)	C5—C6—N1—C8	176.59 (18)
C1—C2—C3—C4	−1.6 (3)	C1—C6—N1—C9	−177.99 (15)
C2—C3—C4—C5	1.7 (3)	C5—C6—N1—C9	0.8 (3)
C2—C3—C4—C7	−177.52 (18)	C10—C9—N1—C8	−94.1 (2)
C3—C4—C5—C6	−0.4 (2)	C10—C9—N1—C6	81.0 (2)
C7—C4—C5—C6	178.76 (17)	N4—C10—N2—C11	0.23 (19)
C2—C1—C6—C5	0.8 (2)	C9—C10—N2—C11	−176.15 (15)
O1—C1—C6—C5	−178.26 (14)	N4—C10—N2—C12	−178.99 (15)
C2—C1—C6—N1	179.81 (15)	C9—C10—N2—C12	4.6 (3)
O1—C1—C6—N1	0.72 (17)	N3—C11—N2—C10	−0.08 (17)
C4—C5—C6—C1	−0.8 (2)	S1—C11—N2—C10	−178.44 (14)
C4—C5—C6—N1	−179.45 (16)	N3—C11—N2—C12	179.15 (15)
N1—C9—C10—N4	20.4 (2)	S1—C11—N2—C12	0.8 (2)
N1—C9—C10—N2	−163.63 (15)	C17—C12—N2—C10	−114.18 (19)
C17—C12—C13—C14	0.7 (3)	C13—C12—N2—C10	65.9 (2)
N2—C12—C13—C14	−179.39 (17)	C17—C12—N2—C11	66.7 (2)
C12—C13—C14—C15	−1.3 (3)	C13—C12—N2—C11	−113.16 (19)
C13—C14—C15—C16	0.7 (3)	N2—C11—N3—N4	−0.1 (2)
C14—C15—C16—C17	0.5 (4)	S1—C11—N3—N4	178.30 (13)
C15—C16—C17—C12	−1.1 (3)	N2—C10—N4—N3	−0.26 (19)
C13—C12—C17—C16	0.5 (3)	C9—C10—N4—N3	176.17 (15)
N2—C12—C17—C16	−179.42 (18)	C11—N3—N4—C10	0.2 (2)
O2—C8—N1—C6	−177.7 (2)	O2—C8—O1—C1	178.11 (19)
O1—C8—N1—C6	2.9 (2)	N1—C8—O1—C1	−2.43 (19)
O2—C8—N1—C9	−1.7 (3)	C2—C1—O1—C8	−178.01 (17)
O1—C8—N1—C9	178.87 (14)	C6—C1—O1—C8	1.03 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^i	0.86 (2)	1.88 (2)	2.743 (2)	178 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.