N-(5-Benzyl-sulfanyl-1,3,4-thia-diazol-2-yl)-2-(piperidin-1-yl)acetamide.

The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzyl-sulfanyl-5-chloro-acetamido-1,3,4-thia-diazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thia-diazole units are twisted by 10.8 (4)°. The thia-diazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S⋯O inter-action of 2.628 (4) Å. In the crystal, mol-ecules form centrosymmetric dimers via N-H⋯N hydrogen bonds. These dimers are further connected by C-H⋯O inter-actions into (100) layers.

Related literature

For physiological properties and syntheses of 1,3,4-thia­diazole derivatives, see: Turner et al. (1988 ▶); Chapleo et al. (1987 ▶); Cleici et al. (2001 ▶); Jain & Mishra (2004 ▶). For the structures of related 1,3,4-thia­diazole derivatives, see: Leung et al. (1992 ▶); Zhang (2009 ▶).

Experimental

Crystal data

C16H20N4OS2

M = 348.48

Monoclinic,

a = 17.429 (4) Å

b = 16.748 (3) Å

c = 5.8390 (12) Å

β = 95.48 (3)°

V = 1696.6 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.92 mm−1

T = 290 K

0.35 × 0.28 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.431, T max = 0.558

7003 measured reflections

2970 independent reflections

1521 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.217

S = 0.98

2970 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S160053681400213X/gk2599sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400213X/gk2599Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400213X/gk2599Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H20N4OS2	F(000) = 736
Mr = 348.48	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Melting point < 376(1) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 17.429 (4) Å	Cell parameters from 124 reflections
b = 16.748 (3) Å	θ = 5.9–35.8°
c = 5.8390 (12) Å	µ = 2.92 mm−1
β = 95.48 (3)°	T = 290 K
V = 1696.6 (6) Å3	Prizmatic, colourless
Z = 4	0.35 × 0.28 × 0.20 mm

Oxford Diffraction Xcalibur Ruby diffractometer	2970 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1521 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
Detector resolution: 10.2576 pixels mm-1	θmax = 66.6°, θmin = 3.7°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = 0→19
Tmin = 0.431, Tmax = 0.558	l = 0→6
7003 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.1068P)2] where P = (Fo2 + 2Fc2)/3
2970 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3, DMSO): 7.30 (5H, m, H–5,6,7,8,9), 6.36 (1H, s, N–H), 4.39 (2H, s, CH2–11), 3.17 (2H, s CH2–3), 2.47 (4H, t, J═5.0 Hz, CH2–12,16), 1.57 (4H, m, CH2–13,15), 1.42 (2H, t, J═5.1 Hz, CH2–14).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.52312 (7)	0.33111 (9)	0.9429 (2)	0.0528 (4)
S2	0.39119 (9)	0.32063 (11)	1.2305 (3)	0.0642 (5)
O1	0.6512 (2)	0.3164 (3)	0.7429 (8)	0.0675 (12)
N1	0.4609 (3)	0.4532 (3)	0.7342 (8)	0.0545 (12)
N2	0.4113 (3)	0.4313 (3)	0.8972 (8)	0.0536 (12)
N3	0.5742 (3)	0.4130 (3)	0.5819 (8)	0.0549 (12)
H3	0.5681	0.4490	0.4769	0.066*
N4	0.7677 (3)	0.3620 (3)	0.4568 (7)	0.0499 (11)
C1	0.5195 (3)	0.4055 (4)	0.7371 (9)	0.0496 (14)
C2	0.4357 (3)	0.3686 (4)	1.0141 (9)	0.0524 (15)
C3	0.3196 (3)	0.3937 (4)	1.3030 (10)	0.0637 (17)
H3B	0.3186	0.3945	1.4688	0.076*
H3C	0.3357	0.4461	1.2561	0.076*
C4	0.2399 (3)	0.3782 (4)	1.1947 (9)	0.0526 (14)
C5	0.2152 (3)	0.4084 (4)	0.9797 (10)	0.0641 (17)
H5A	0.2496	0.4359	0.8964	0.077*
C6	0.1403 (4)	0.3980 (5)	0.8881 (11)	0.074 (2)
H6A	0.1248	0.4181	0.7426	0.089*
C7	0.0882 (4)	0.3586 (4)	1.0077 (12)	0.0730 (19)
H7A	0.0371	0.3534	0.9472	0.088*
C8	0.1127 (4)	0.3267 (5)	1.2187 (12)	0.077 (2)
H8A	0.0782	0.2981	1.2991	0.093*
C9	0.1871 (3)	0.3364 (4)	1.3124 (11)	0.0677 (18)
H9A	0.2025	0.3147	1.4562	0.081*
C10	0.6380 (3)	0.3646 (4)	0.5903 (10)	0.0500 (14)
C11	0.6864 (3)	0.3734 (4)	0.3892 (9)	0.0550 (15)
H11A	0.6694	0.3347	0.2717	0.066*
H11B	0.6784	0.4263	0.3231	0.066*
C12	0.8104 (3)	0.3476 (4)	0.2561 (10)	0.0606 (16)
H12A	0.8052	0.3935	0.1545	0.073*
H12B	0.7888	0.3016	0.1719	0.073*
C13	0.8937 (3)	0.3331 (4)	0.3287 (11)	0.0691 (18)
H13A	0.9210	0.3260	0.1930	0.083*
H13B	0.8988	0.2841	0.4176	0.083*
C14	0.9299 (3)	0.4006 (5)	0.4705 (11)	0.074 (2)
H14A	0.9324	0.4477	0.3750	0.089*
H14B	0.9821	0.3862	0.5281	0.089*
C15	0.8832 (4)	0.4190 (5)	0.6722 (11)	0.075 (2)
H15A	0.8879	0.3751	0.7811	0.090*
H15B	0.9032	0.4667	0.7506	0.090*
C16	0.7994 (3)	0.4313 (4)	0.5881 (10)	0.0592 (16)
H16A	0.7701	0.4401	0.7188	0.071*
H16B	0.7944	0.4784	0.4914	0.071*

	U11	U22	U33	U12	U13	U23
S1	0.0408 (7)	0.0584 (9)	0.0596 (9)	0.0043 (7)	0.0063 (6)	0.0094 (8)
S2	0.0531 (8)	0.0744 (11)	0.0673 (10)	0.0131 (8)	0.0177 (7)	0.0167 (9)
O1	0.053 (2)	0.074 (3)	0.077 (3)	0.014 (2)	0.017 (2)	0.030 (3)
N1	0.051 (3)	0.053 (3)	0.059 (3)	0.008 (2)	0.006 (2)	0.007 (2)
N2	0.045 (3)	0.055 (3)	0.062 (3)	0.004 (2)	0.011 (2)	0.008 (3)
N3	0.045 (2)	0.064 (3)	0.055 (3)	0.001 (2)	0.005 (2)	0.014 (3)
N4	0.045 (2)	0.058 (3)	0.047 (3)	0.002 (2)	0.0067 (19)	−0.003 (2)
C1	0.036 (3)	0.058 (4)	0.054 (3)	−0.001 (2)	0.000 (2)	0.003 (3)
C2	0.042 (3)	0.063 (4)	0.052 (3)	−0.001 (3)	0.004 (2)	−0.003 (3)
C3	0.053 (3)	0.085 (5)	0.054 (4)	0.005 (3)	0.008 (3)	−0.007 (3)
C4	0.050 (3)	0.059 (4)	0.050 (3)	0.004 (3)	0.011 (2)	−0.001 (3)
C5	0.057 (4)	0.079 (5)	0.057 (4)	0.000 (3)	0.012 (3)	0.012 (3)
C6	0.065 (4)	0.092 (6)	0.063 (4)	0.006 (4)	−0.001 (3)	0.009 (4)
C7	0.047 (3)	0.085 (5)	0.086 (5)	0.000 (3)	0.003 (3)	−0.002 (4)
C8	0.056 (4)	0.090 (5)	0.089 (5)	−0.006 (4)	0.025 (3)	0.016 (4)
C9	0.059 (4)	0.088 (5)	0.058 (4)	0.007 (3)	0.015 (3)	0.018 (4)
C10	0.040 (3)	0.050 (3)	0.060 (4)	−0.002 (2)	0.005 (2)	−0.002 (3)
C11	0.050 (3)	0.060 (4)	0.055 (3)	0.002 (3)	0.007 (3)	0.003 (3)
C12	0.061 (4)	0.070 (4)	0.052 (3)	−0.002 (3)	0.012 (3)	−0.012 (3)
C13	0.056 (3)	0.084 (5)	0.070 (4)	0.008 (4)	0.022 (3)	−0.011 (4)
C14	0.044 (3)	0.099 (6)	0.078 (5)	−0.003 (3)	0.004 (3)	−0.005 (4)
C15	0.054 (4)	0.102 (6)	0.071 (4)	−0.006 (4)	0.007 (3)	−0.027 (4)
C16	0.054 (3)	0.066 (4)	0.058 (4)	0.001 (3)	0.013 (3)	−0.014 (3)

S1—C1	1.728 (6)	C7—C8	1.373 (9)
S1—C2	1.736 (5)	C7—H7A	0.9300
S2—C2	1.741 (6)	C8—C9	1.368 (9)
S2—C3	1.825 (6)	C8—H8A	0.9300
O1—C10	1.208 (7)	C9—H9A	0.9300
N1—C1	1.295 (7)	C10—C11	1.517 (7)
N1—N2	1.394 (6)	C11—H11A	0.9700
N2—C2	1.301 (8)	C11—H11B	0.9700
N3—C10	1.372 (7)	C12—C13	1.492 (8)
N3—C1	1.383 (7)	C12—H12A	0.9700
N3—H3	0.8600	C12—H12B	0.9700
N4—C11	1.448 (7)	C13—C14	1.504 (9)
N4—C12	1.467 (7)	C13—H13A	0.9700
N4—C16	1.469 (7)	C13—H13B	0.9700
C3—C4	1.493 (8)	C14—C15	1.527 (8)
C3—H3B	0.9700	C14—H14A	0.9700
C3—H3C	0.9700	C14—H14B	0.9700
C4—C5	1.383 (8)	C15—C16	1.509 (8)
C4—C9	1.390 (8)	C15—H15A	0.9700
C5—C6	1.373 (8)	C15—H15B	0.9700
C5—H5A	0.9300	C16—H16A	0.9700
C6—C7	1.368 (9)	C16—H16B	0.9700
C6—H6A	0.9300
C1—S1—C2	86.0 (3)	O1—C10—N3	121.2 (5)
C2—S2—C3	102.7 (3)	O1—C10—C11	123.7 (5)
C1—N1—N2	111.6 (5)	N3—C10—C11	115.0 (5)
C2—N2—N1	112.3 (4)	N4—C11—C10	112.2 (5)
C10—N3—C1	122.1 (5)	N4—C11—H11A	109.2
C10—N3—H3	119.0	C10—C11—H11A	109.2
C1—N3—H3	119.0	N4—C11—H11B	109.2
C11—N4—C12	111.3 (4)	C10—C11—H11B	109.2
C11—N4—C16	110.3 (5)	H11A—C11—H11B	107.9
C12—N4—C16	110.6 (5)	N4—C12—C13	110.7 (5)
N1—C1—N3	121.9 (5)	N4—C12—H12A	109.5
N1—C1—S1	115.5 (4)	C13—C12—H12A	109.5
N3—C1—S1	122.6 (4)	N4—C12—H12B	109.5
N2—C2—S1	114.6 (4)	C13—C12—H12B	109.5
N2—C2—S2	127.4 (4)	H12A—C12—H12B	108.1
S1—C2—S2	118.0 (4)	C12—C13—C14	112.3 (5)
C4—C3—S2	114.5 (5)	C12—C13—H13A	109.1
C4—C3—H3B	108.6	C14—C13—H13A	109.1
S2—C3—H3B	108.6	C12—C13—H13B	109.1
C4—C3—H3C	108.6	C14—C13—H13B	109.1
S2—C3—H3C	108.6	H13A—C13—H13B	107.9
H3B—C3—H3C	107.6	C13—C14—C15	110.4 (5)
C5—C4—C9	118.0 (6)	C13—C14—H14A	109.6
C5—C4—C3	121.2 (5)	C15—C14—H14A	109.6
C9—C4—C3	120.7 (6)	C13—C14—H14B	109.6
C6—C5—C4	120.6 (6)	C15—C14—H14B	109.6
C6—C5—H5A	119.7	H14A—C14—H14B	108.1
C4—C5—H5A	119.7	C16—C15—C14	110.3 (5)
C7—C6—C5	121.0 (7)	C16—C15—H15A	109.6
C7—C6—H6A	119.5	C14—C15—H15A	109.6
C5—C6—H6A	119.5	C16—C15—H15B	109.6
C6—C7—C8	118.7 (6)	C14—C15—H15B	109.6
C6—C7—H7A	120.6	H15A—C15—H15B	108.1
C8—C7—H7A	120.6	N4—C16—C15	111.5 (5)
C9—C8—C7	121.0 (6)	N4—C16—H16A	109.3
C9—C8—H8A	119.5	C15—C16—H16A	109.3
C7—C8—H8A	119.5	N4—C16—H16B	109.3
C8—C9—C4	120.6 (6)	C15—C16—H16B	109.3
C8—C9—H9A	119.7	H16A—C16—H16B	108.0
C4—C9—H9A	119.7
C1—N1—N2—C2	0.3 (7)	C5—C6—C7—C8	−2.4 (12)
N2—N1—C1—N3	176.5 (5)	C6—C7—C8—C9	2.3 (12)
N2—N1—C1—S1	−2.1 (7)	C7—C8—C9—C4	−0.6 (12)
C10—N3—C1—N1	177.3 (5)	C5—C4—C9—C8	−1.1 (10)
C10—N3—C1—S1	−4.2 (8)	C3—C4—C9—C8	175.8 (6)
C2—S1—C1—N1	2.5 (5)	C1—N3—C10—O1	−4.4 (9)
C2—S1—C1—N3	−176.1 (5)	C1—N3—C10—C11	172.2 (5)
N1—N2—C2—S1	1.7 (7)	C12—N4—C11—C10	163.5 (5)
N1—N2—C2—S2	−179.1 (4)	C16—N4—C11—C10	−73.3 (6)
C1—S1—C2—N2	−2.3 (5)	O1—C10—C11—N4	−37.3 (8)
C1—S1—C2—S2	178.4 (4)	N3—C10—C11—N4	146.2 (5)
C3—S2—C2—N2	−14.8 (6)	C11—N4—C12—C13	−178.0 (5)
C3—S2—C2—S1	164.4 (3)	C16—N4—C12—C13	58.9 (7)
C2—S2—C3—C4	99.2 (5)	N4—C12—C13—C14	−56.4 (7)
S2—C3—C4—C5	−88.5 (7)	C12—C13—C14—C15	52.9 (8)
S2—C3—C4—C9	94.7 (6)	C13—C14—C15—C16	−52.0 (8)
C9—C4—C5—C6	1.0 (10)	C11—N4—C16—C15	176.8 (5)
C3—C4—C5—C6	−175.9 (6)	C12—N4—C16—C15	−59.6 (7)
C4—C5—C6—C7	0.7 (12)	C14—C15—C16—N4	56.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1i	0.86	2.08	2.930 (7)	169
C11—H11A···O1ii	0.97	2.55	3.334 (8)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1i	0.86	2.08	2.930 (7)	169
C11—H11A⋯O1ii	0.97	2.55	3.334 (8)	138

Symmetry codes: (i) ; (ii) .