3-[(4-Phenyl-piperazin-1-yl)meth-yl]-5-(thio-phen-2-yl)-2,3-di-hydro-1,3,4-oxa-diazole-2-thione.

In the title compound, C17H18N4OS2, the 2-thienyl ring is disordered over two co-planar, opposite orientations in a 0.684 (2): 0.316 ratio. The 1,3,4-oxa-diazole ring is almost co-planar with the attached 2-thienyl ring [dihedral angles of 5.34 (19) and 4.8 (5)° for the major and minor components, respectively]. The relative disposition of the thione- and ring-S atoms is anti for the major orientation of the 2-thienyl residue. Overall, the shape of the mol-ecule approximates the letter V. In the crystal, a three-dimensional architecture is consolidated by a combination of weak C-H⋯S and C-H⋯π contacts.

Related literature

For background to the biological properties of 1,3,4-oxa­diazole derivatives, see: Al-Omar (2010 ▶). For a related structure, see: El-Emam et al. (2012 ▶).

Experimental

Crystal data

C17H18N4OS2

M = 358.47

Monoclinic,

a = 26.1721 (17) Å

b = 5.7253 (3) Å

c = 23.7008 (18) Å

β = 97.802 (6)°

V = 3518.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.887, T max = 1.000

9546 measured reflections

4083 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.06

4083 reflections

230 parameters

33 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009252/hb7064sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009252/hb7064Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009252/hb7064Isup3.cml

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

C17H18N4OS2	F(000) = 1504
Mr = 358.47	Dx = 1.353 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2605 reflections
a = 26.1721 (17) Å	θ = 3.1–27.5°
b = 5.7253 (3) Å	µ = 0.31 mm−1
c = 23.7008 (18) Å	T = 295 K
β = 97.802 (6)°	Prism, light-brown
V = 3518.5 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 8

Agilent SuperNova Dual diffractometer with Atlas detector	4083 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2797 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −32→34
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −7→5
Tmin = 0.887, Tmax = 1.000	l = −16→30
9546 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.9031P] where P = (Fo2 + 2Fc2)/3
4083 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.25 e Å−3
33 restraints	Δρmin = −0.26 e Å−3

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	Occ. (<1)
S1	0.51012 (6)	0.4713 (3)	0.35472 (6)	0.0619 (3)	0.684 (2)
S1'	0.51936 (13)	0.8668 (6)	0.43201 (16)	0.0619 (3)	0.316
S2	0.35703 (2)	0.65396 (10)	0.54603 (3)	0.0727 (2)
O1	0.43151 (5)	0.6708 (2)	0.47998 (5)	0.0534 (3)
N1	0.41826 (6)	0.3583 (3)	0.42460 (7)	0.0522 (4)
N2	0.38163 (6)	0.3737 (3)	0.46156 (7)	0.0509 (4)
N3	0.29660 (6)	0.2250 (3)	0.41864 (7)	0.0556 (4)
N4	0.22283 (6)	0.3760 (2)	0.32601 (6)	0.0489 (4)
C1	0.55629 (17)	0.6849 (7)	0.3488 (3)	0.0629 (13)	0.684 (2)
H1	0.5786	0.6799	0.3215	0.076*	0.684 (2)
C2	0.5569 (3)	0.8585 (13)	0.3874 (2)	0.0655 (13)	0.684 (2)
H2	0.5783	0.9889	0.3899	0.079*	0.684 (2)
C3	0.5214 (2)	0.8105 (7)	0.4216 (2)	0.0673 (14)	0.684 (2)
H3	0.5180	0.9064	0.4526	0.081*	0.684 (2)
C1'	0.5583 (6)	0.821 (3)	0.3787 (6)	0.0629 (13)	0.316 (2)
H1'	0.5844	0.9250	0.3726	0.076*	0.316 (2)
C2'	0.5483 (5)	0.627 (2)	0.3469 (7)	0.0655 (13)	0.316 (2)
H2'	0.5649	0.5826	0.3163	0.079*	0.316 (2)
C3'	0.5102 (5)	0.509 (2)	0.3670 (6)	0.0673 (14)	0.316 (2)
H3'	0.4984	0.3649	0.3524	0.081*	0.316 (2)
C4	0.49000 (7)	0.6179 (3)	0.41049 (8)	0.0506 (4)
C5	0.44667 (7)	0.5396 (3)	0.43703 (8)	0.0481 (4)
C6	0.38888 (7)	0.5603 (3)	0.49568 (8)	0.0524 (5)
C7	0.34040 (8)	0.1950 (3)	0.46076 (10)	0.0613 (5)
H7A	0.3554	0.0431	0.4552	0.074*
H7B	0.3287	0.1934	0.4979	0.074*
C8	0.26756 (8)	0.4377 (4)	0.42299 (9)	0.0685 (6)
H8A	0.2869	0.5698	0.4115	0.082*
H8B	0.2619	0.4616	0.4622	0.082*
C9	0.21648 (8)	0.4220 (5)	0.38539 (9)	0.0721 (6)
H9A	0.1961	0.2980	0.3991	0.086*
H9B	0.1978	0.5675	0.3876	0.086*
C10	0.25448 (8)	0.1688 (3)	0.32178 (10)	0.0628 (5)
H10A	0.2608	0.1490	0.2827	0.075*
H10B	0.2362	0.0320	0.3325	0.075*
C11	0.30534 (8)	0.1901 (4)	0.36017 (9)	0.0632 (6)
H11A	0.3255	0.0493	0.3575	0.076*
H11B	0.3247	0.3209	0.3480	0.076*
C12	0.17704 (7)	0.3921 (3)	0.28724 (8)	0.0473 (4)
C13	0.14489 (8)	0.5860 (3)	0.28800 (9)	0.0573 (5)
H13	0.1536	0.7033	0.3147	0.069*
C14	0.10056 (9)	0.6071 (4)	0.25001 (10)	0.0654 (6)
H14	0.0799	0.7384	0.2515	0.078*
C15	0.08620 (9)	0.4380 (4)	0.20978 (10)	0.0670 (6)
H15	0.0560	0.4528	0.1843	0.080*
C16	0.11754 (9)	0.2471 (4)	0.20823 (9)	0.0658 (6)
H16	0.1085	0.1314	0.1812	0.079*
C17	0.16222 (8)	0.2226 (3)	0.24588 (9)	0.0579 (5)
H17	0.1828	0.0913	0.2437	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0542 (5)	0.0638 (7)	0.0700 (7)	−0.0048 (4)	0.0171 (5)	−0.0069 (5)
S1'	0.0542 (5)	0.0638 (7)	0.0700 (7)	−0.0048 (4)	0.0171 (5)	−0.0069 (5)
S2	0.0815 (4)	0.0786 (4)	0.0626 (4)	0.0100 (3)	0.0265 (3)	0.0018 (3)
O1	0.0542 (8)	0.0540 (7)	0.0521 (8)	−0.0023 (6)	0.0082 (6)	0.0000 (6)
N1	0.0470 (9)	0.0554 (9)	0.0546 (10)	−0.0002 (7)	0.0086 (7)	0.0011 (7)
N2	0.0456 (9)	0.0535 (8)	0.0541 (9)	0.0008 (7)	0.0089 (7)	0.0064 (7)
N3	0.0471 (9)	0.0608 (9)	0.0604 (10)	−0.0044 (8)	0.0124 (8)	0.0048 (8)
N4	0.0457 (8)	0.0541 (8)	0.0491 (9)	−0.0023 (7)	0.0142 (7)	−0.0106 (7)
C1	0.052 (2)	0.058 (3)	0.083 (3)	−0.0088 (18)	0.025 (2)	0.003 (2)
C2	0.061 (2)	0.062 (3)	0.075 (3)	−0.0087 (19)	0.015 (2)	0.0010 (19)
C3	0.078 (3)	0.056 (3)	0.068 (3)	0.006 (2)	0.011 (2)	−0.0046 (19)
C1'	0.052 (2)	0.058 (3)	0.083 (3)	−0.0088 (18)	0.025 (2)	0.003 (2)
C2'	0.061 (2)	0.062 (3)	0.075 (3)	−0.0087 (19)	0.015 (2)	0.0010 (19)
C3'	0.078 (3)	0.056 (3)	0.068 (3)	0.006 (2)	0.011 (2)	−0.0046 (19)
C4	0.0448 (10)	0.0544 (10)	0.0516 (11)	0.0005 (8)	0.0032 (8)	0.0050 (8)
C5	0.0453 (10)	0.0513 (10)	0.0464 (10)	0.0046 (8)	0.0018 (8)	0.0041 (8)
C6	0.0522 (11)	0.0542 (10)	0.0505 (11)	0.0052 (9)	0.0065 (9)	0.0097 (9)
C7	0.0594 (13)	0.0566 (11)	0.0689 (14)	−0.0061 (10)	0.0121 (10)	0.0156 (10)
C8	0.0593 (13)	0.0951 (15)	0.0518 (12)	0.0152 (12)	0.0097 (10)	−0.0165 (11)
C9	0.0537 (12)	0.1097 (17)	0.0543 (13)	0.0173 (12)	0.0127 (10)	−0.0143 (12)
C10	0.0535 (12)	0.0641 (12)	0.0714 (14)	0.0021 (10)	0.0102 (10)	−0.0198 (10)
C11	0.0507 (12)	0.0677 (12)	0.0729 (15)	0.0054 (10)	0.0142 (10)	−0.0162 (10)
C12	0.0469 (10)	0.0488 (9)	0.0491 (10)	−0.0100 (8)	0.0165 (8)	−0.0018 (8)
C13	0.0612 (12)	0.0507 (10)	0.0609 (13)	−0.0047 (10)	0.0120 (10)	−0.0051 (9)
C14	0.0651 (14)	0.0591 (12)	0.0713 (15)	0.0052 (10)	0.0072 (11)	0.0040 (11)
C15	0.0656 (14)	0.0697 (13)	0.0628 (14)	−0.0044 (11)	−0.0026 (11)	0.0052 (11)
C16	0.0708 (14)	0.0665 (13)	0.0575 (13)	−0.0078 (11)	−0.0003 (11)	−0.0100 (10)
C17	0.0606 (12)	0.0551 (10)	0.0585 (12)	−0.0020 (9)	0.0098 (10)	−0.0077 (9)

S1—C4	1.708 (2)	C3'—C4	1.371 (9)
S1—C1	1.738 (3)	C3'—H3'	0.9300
S1'—C4	1.666 (3)	C4—C5	1.441 (3)
S1'—C1'	1.748 (9)	C7—H7A	0.9700
S2—C6	1.636 (2)	C7—H7B	0.9700
O1—C5	1.367 (2)	C8—C9	1.505 (3)
O1—C6	1.377 (2)	C8—H8A	0.9700
N1—C5	1.288 (2)	C8—H8B	0.9700
N1—N2	1.386 (2)	C9—H9A	0.9700
N2—C6	1.338 (2)	C9—H9B	0.9700
N2—C7	1.485 (2)	C10—C11	1.512 (3)
N3—C7	1.425 (3)	C10—H10A	0.9700
N3—C8	1.447 (3)	C10—H10B	0.9700
N3—C11	1.449 (3)	C11—H11A	0.9700
N4—C12	1.411 (2)	C11—H11B	0.9700
N4—C10	1.458 (2)	C12—C13	1.395 (3)
N4—C9	1.463 (2)	C12—C17	1.396 (3)
C1—C2	1.349 (5)	C13—C14	1.374 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.342 (7)	C14—C15	1.375 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.379 (5)	C15—C16	1.370 (3)
C3—H3	0.9300	C15—H15	0.9300
C1'—C2'	1.349 (8)	C16—C17	1.379 (3)
C1'—H1'	0.9300	C16—H16	0.9300
C2'—C3'	1.344 (10)	C17—H17	0.9300
C2'—H2'	0.9300
C4—S1—C1	90.4 (2)	N2—C7—H7A	108.3
C4—S1'—C1'	86.7 (6)	N3—C7—H7B	108.3
C5—O1—C6	106.05 (14)	N2—C7—H7B	108.3
C5—N1—N2	103.39 (14)	H7A—C7—H7B	107.4
C6—N2—N1	112.28 (15)	N3—C8—C9	109.90 (18)
C6—N2—C7	126.94 (16)	N3—C8—H8A	109.7
N1—N2—C7	120.78 (15)	C9—C8—H8A	109.7
C7—N3—C8	115.60 (17)	N3—C8—H8B	109.7
C7—N3—C11	115.92 (16)	C9—C8—H8B	109.7
C8—N3—C11	109.70 (16)	H8A—C8—H8B	108.2
C12—N4—C10	116.68 (15)	N4—C9—C8	111.87 (16)
C12—N4—C9	114.66 (14)	N4—C9—H9A	109.2
C10—N4—C9	110.64 (17)	C8—C9—H9A	109.2
C2—C1—S1	114.1 (6)	N4—C9—H9B	109.2
C2—C1—H1	122.9	C8—C9—H9B	109.2
S1—C1—H1	122.9	H9A—C9—H9B	107.9
C3—C2—C1	108.2 (7)	N4—C10—C11	110.80 (16)
C3—C2—H2	125.9	N4—C10—H10A	109.5
C1—C2—H2	125.9	C11—C10—H10A	109.5
C2—C3—C4	119.4 (5)	N4—C10—H10B	109.5
C2—C3—H3	120.3	C11—C10—H10B	109.5
C4—C3—H3	120.3	H10A—C10—H10B	108.1
C2'—C1'—S1'	115.9 (14)	N3—C11—C10	110.26 (16)
C2'—C1'—H1'	122.0	N3—C11—H11A	109.6
S1'—C1'—H1'	122.0	C10—C11—H11A	109.6
C3'—C2'—C1'	108.4 (16)	N3—C11—H11B	109.6
C3'—C2'—H2'	125.8	C10—C11—H11B	109.6
C1'—C2'—H2'	125.8	H11A—C11—H11B	108.1
C2'—C3'—C4	114.7 (12)	C13—C12—C17	116.86 (19)
C2'—C3'—H3'	122.7	C13—C12—N4	120.30 (16)
C4—C3'—H3'	122.7	C17—C12—N4	122.82 (17)
C3'—C4—C3	103.2 (6)	C14—C13—C12	121.24 (19)
C3'—C4—C5	126.4 (6)	C14—C13—H13	119.4
C3—C4—C5	130.4 (2)	C12—C13—H13	119.4
C3'—C4—S1'	114.2 (6)	C13—C14—C15	121.3 (2)
C5—C4—S1'	119.33 (17)	C13—C14—H14	119.3
C3—C4—S1	107.6 (2)	C15—C14—H14	119.3
C5—C4—S1	121.91 (15)	C16—C15—C14	118.2 (2)
S1'—C4—S1	118.65 (15)	C16—C15—H15	120.9
N1—C5—O1	113.36 (16)	C14—C15—H15	120.9
N1—C5—C4	127.95 (17)	C15—C16—C17	121.5 (2)
O1—C5—C4	118.66 (16)	C15—C16—H16	119.3
N2—C6—O1	104.91 (15)	C17—C16—H16	119.3
N2—C6—S2	131.15 (15)	C16—C17—C12	120.94 (19)
O1—C6—S2	123.94 (15)	C16—C17—H17	119.5
N3—C7—N2	116.10 (15)	C12—C17—H17	119.5
N3—C7—H7A	108.3
C5—N1—N2—C6	−0.7 (2)	S1'—C4—C5—O1	−1.2 (3)
C5—N1—N2—C7	179.54 (16)	S1—C4—C5—O1	−177.46 (15)
C4—S1—C1—C2	0.5 (3)	N1—N2—C6—O1	0.5 (2)
S1—C1—C2—C3	1.9 (5)	C7—N2—C6—O1	−179.85 (16)
C1—C2—C3—C4	−4.4 (7)	N1—N2—C6—S2	−179.55 (15)
C4—S1'—C1'—C2'	0.4 (9)	C7—N2—C6—S2	0.1 (3)
S1'—C1'—C2'—C3'	−2.3 (13)	C5—O1—C6—N2	−0.01 (18)
C1'—C2'—C3'—C4	3.5 (16)	C5—O1—C6—S2	−179.99 (14)
C2'—C3'—C4—C3	−5.5 (13)	C8—N3—C7—N2	−61.8 (2)
C2'—C3'—C4—C5	175.2 (9)	C11—N3—C7—N2	68.7 (2)
C2'—C3'—C4—S1'	−3.4 (17)	C6—N2—C7—N3	97.8 (2)
C2'—C3'—C4—S1	152 (10)	N1—N2—C7—N3	−82.5 (2)
C2—C3—C4—C3'	6.7 (7)	C7—N3—C8—C9	−166.94 (17)
C2—C3—C4—C5	−174.1 (4)	C11—N3—C8—C9	59.7 (2)
C2—C3—C4—S1'	−164 (2)	C12—N4—C9—C8	−171.40 (17)
C2—C3—C4—S1	4.7 (7)	C10—N4—C9—C8	54.1 (2)
C1'—S1'—C4—C3'	1.7 (11)	N3—C8—C9—N4	−56.9 (3)
C1'—S1'—C4—C3	12 (2)	C12—N4—C10—C11	172.40 (16)
C1'—S1'—C4—C5	−177.1 (6)	C9—N4—C10—C11	−54.1 (2)
C1'—S1'—C4—S1	−0.7 (6)	C7—N3—C11—C10	166.26 (16)
C1—S1—C4—C3'	−26 (9)	C8—N3—C11—C10	−60.6 (2)
C1—S1—C4—C3	−2.6 (4)	N4—C10—C11—N3	57.9 (2)
C1—S1—C4—C5	176.2 (2)	C10—N4—C12—C13	−179.25 (17)
C1—S1—C4—S1'	−0.1 (3)	C9—N4—C12—C13	49.1 (2)
N2—N1—C5—O1	0.74 (19)	C10—N4—C12—C17	−1.0 (2)
N2—N1—C5—C4	−177.59 (17)	C9—N4—C12—C17	−132.6 (2)
C6—O1—C5—N1	−0.5 (2)	C17—C12—C13—C14	0.5 (3)
C6—O1—C5—C4	178.00 (15)	N4—C12—C13—C14	178.91 (17)
C3'—C4—C5—N1	−1.5 (9)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—N1	179.4 (4)	C13—C14—C15—C16	−0.4 (3)
S1'—C4—C5—N1	177.1 (2)	C14—C15—C16—C17	0.3 (3)
S1—C4—C5—N1	0.8 (3)	C15—C16—C17—C12	0.2 (3)
C3'—C4—C5—O1	−179.8 (9)	C13—C12—C17—C16	−0.6 (3)
C3—C4—C5—O1	1.1 (4)	N4—C12—C17—C16	−178.96 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···S2i	0.97	2.77	3.618 (3)	146
C1—H1···Cg1ii	0.93	2.72	3.545 (6)	148
C11—H11A···Cg1iii	0.97	2.98	3.600 (2)	123
C15—H15···Cg2iii	0.93	2.95	3.743 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O1,N1,N2,C5,C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯S2i	0.97	2.77	3.618 (3)	146
C1—H1⋯Cg1ii	0.93	2.72	3.545 (6)	148
C11—H11A⋯Cg1iii	0.97	2.98	3.600 (2)	123
C15—H15⋯Cg2iii	0.93	2.95	3.743 (3)	144

Symmetry codes: (i) ; (ii) ; (iii) .