N-(2-Furylcarbon-yl)piperidine-1-carbo-thio-amide.

The title compound, C(11)H(14)N(2)O(2)S, was synthesized from furoyl isothio-cyanate and piperidine in dry acetone. The thio-urea group is in the thio-amide form. The thio-urea group makes a dihedral angle of 53.9 (1)° with the furan carbonyl group. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming one-dimensional chains along the c axis. An intramolecular N-H⋯O hydrogen bond is also present.

Related literature

For general background, see: Aly et al. (2007 ▶); Estévez-Hernández et al. (2006 ▶, 2007 ▶); Koch (2001 ▶). For related structures, see: Dago et al. (1987 ▶); Plutin et al. (2000 ▶); Pérez et al. (2008 ▶); Duque et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).

Experimental

Crystal data

C11H14N2O2S

M = 238.3

Orthorhombic,

a = 31.6377 (15) Å

b = 8.6787 (4) Å

c = 8.5308 (3) Å

V = 2342.34 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.15 × 0.13 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

4308 measured reflections

2387 independent reflections

1550 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.205

S = 1.10

2387 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.35 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020977/ww2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020977/ww2121Isup2.hkl

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

C11H14N2O2S1	F000 = 1008
Mr = 238.3	Dx = 1.352 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2684 reflections
a = 31.6377 (15) Å	θ = 2.9–26.4º
b = 8.6787 (4) Å	µ = 0.26 mm−1
c = 8.5308 (3) Å	T = 294 K
V = 2342.34 (18) Å3	Prism, colourless
Z = 8	0.15 × 0.13 × 0.06 mm

Nonius KappaCCD diffractometer	Rint = 0.039
CCD rotation images, thick slices scans	θmax = 26.4º
Absorption correction: none	θmin = 3.4º
4308 measured reflections	h = −39→39
2387 independent reflections	k = −10→10
1550 reflections with I > 2σ(I)	l = −10→10

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.1017P)2 + 1.0533P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.067	(Δ/σ)max < 0.001
wR(F2) = 0.205	Δρmax = 0.35 e Å−3
S = 1.11	Δρmin = −0.35 e Å−3
2387 reflections	Extinction correction: none
145 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.05964 (9)	0.3587 (4)	0.2251 (4)	0.0455 (7)
C2	0.13205 (9)	0.2817 (4)	0.2882 (3)	0.0456 (8)
C3	0.01610 (9)	0.3667 (3)	0.2812 (3)	0.0442 (7)
C4	−0.01794 (10)	0.4368 (4)	0.2179 (4)	0.0561 (9)
H4	−0.0191	0.4904	0.1237	0.067*
C5	−0.05161 (11)	0.4118 (4)	0.3246 (5)	0.0678 (11)
H5	−0.0792	0.4468	0.314	0.081*
C6	−0.03631 (12)	0.3293 (5)	0.4421 (5)	0.0776 (12)
H6	−0.0521	0.2957	0.5275	0.093*
C7	0.13358 (12)	0.5686 (4)	0.2859 (5)	0.0627 (10)
H7A	0.1051	0.5591	0.3268	0.075*
H7B	0.1321	0.6226	0.1865	0.075*
C8	0.16045 (13)	0.6593 (4)	0.3996 (5)	0.0743 (11)
H8A	0.1586	0.6123	0.5026	0.089*
H8B	0.1495	0.7633	0.4075	0.089*
C9	0.20640 (14)	0.6656 (5)	0.3497 (6)	0.0890 (13)
H9A	0.209	0.7254	0.2541	0.107*
H9B	0.223	0.7157	0.4305	0.107*
C10	0.22286 (12)	0.5045 (5)	0.3226 (6)	0.0849 (13)
H10A	0.2515	0.5098	0.2827	0.102*
H10B	0.2235	0.4492	0.4213	0.102*
C11	0.19565 (11)	0.4186 (5)	0.2081 (5)	0.0703 (11)
H11A	0.197	0.4688	0.1065	0.084*
H11B	0.2062	0.3143	0.1962	0.084*
N1	0.08854 (7)	0.2942 (3)	0.3243 (3)	0.0458 (7)
H1	0.0799	0.2594	0.4131	0.055*
N2	0.15184 (8)	0.4140 (3)	0.2619 (3)	0.0527 (7)
O1	0.06909 (7)	0.4111 (3)	0.0970 (2)	0.0569 (7)
O2	0.00546 (7)	0.3001 (3)	0.4214 (3)	0.0651 (7)
S1	0.15400 (3)	0.10814 (10)	0.28587 (13)	0.0661 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0424 (16)	0.0478 (17)	0.0462 (19)	0.0006 (13)	−0.0034 (13)	−0.0070 (15)
C2	0.0397 (15)	0.056 (2)	0.0412 (17)	−0.0007 (14)	−0.0028 (13)	−0.0054 (15)
C3	0.0435 (16)	0.0484 (17)	0.0406 (16)	0.0015 (13)	−0.0001 (13)	0.0006 (14)
C4	0.0547 (19)	0.0541 (19)	0.060 (2)	0.0076 (16)	−0.0086 (16)	0.0046 (17)
C5	0.0423 (18)	0.070 (2)	0.091 (3)	0.0139 (17)	0.0037 (18)	−0.004 (2)
C6	0.050 (2)	0.092 (3)	0.090 (3)	0.018 (2)	0.023 (2)	0.017 (2)
C7	0.057 (2)	0.049 (2)	0.082 (3)	0.0016 (16)	0.0006 (18)	0.0000 (18)
C8	0.089 (3)	0.048 (2)	0.086 (3)	−0.0092 (19)	−0.006 (2)	−0.005 (2)
C9	0.082 (3)	0.074 (3)	0.111 (3)	−0.027 (2)	−0.018 (3)	0.002 (3)
C10	0.053 (2)	0.084 (3)	0.118 (4)	−0.017 (2)	−0.011 (2)	0.009 (3)
C11	0.0438 (19)	0.079 (3)	0.088 (3)	−0.0093 (18)	0.0112 (18)	−0.006 (2)
N1	0.0374 (13)	0.0569 (17)	0.0430 (14)	0.0020 (11)	0.0016 (10)	0.0006 (12)
N2	0.0419 (15)	0.0509 (16)	0.0655 (18)	−0.0043 (12)	0.0023 (12)	−0.0071 (13)
O1	0.0537 (13)	0.0760 (17)	0.0411 (13)	−0.0015 (11)	0.0017 (10)	0.0051 (11)
O2	0.0520 (13)	0.0813 (18)	0.0619 (15)	0.0160 (12)	0.0121 (11)	0.0164 (13)
S1	0.0485 (5)	0.0536 (6)	0.0962 (8)	0.0069 (4)	−0.0001 (4)	−0.0080 (5)

C1—O1	1.221 (4)	C7—H7A	0.97
C1—N1	1.366 (4)	C7—H7B	0.97
C1—C3	1.460 (4)	C8—C9	1.516 (6)
C2—N2	1.327 (4)	C8—H8A	0.97
C2—N1	1.415 (4)	C8—H8B	0.97
C2—S1	1.659 (3)	C9—C10	1.510 (7)
C3—C4	1.349 (4)	C9—H9A	0.97
C3—O2	1.371 (4)	C9—H9B	0.97
C4—C5	1.418 (5)	C10—C11	1.500 (5)
C4—H4	0.93	C10—H10A	0.97
C5—C6	1.323 (5)	C10—H10B	0.97
C5—H5	0.93	C11—N2	1.461 (4)
C6—O2	1.357 (4)	C11—H11A	0.97
C6—H6	0.93	C11—H11B	0.97
C7—N2	1.475 (4)	N1—H1	0.86
C7—C8	1.511 (5)
O1—C1—N1	122.9 (3)	C9—C8—H8B	109.2
O1—C1—C3	120.4 (3)	H8A—C8—H8B	107.9
N1—C1—C3	116.6 (3)	C10—C9—C8	109.9 (3)
N2—C2—N1	115.5 (3)	C10—C9—H9A	109.7
N2—C2—S1	125.9 (2)	C8—C9—H9A	109.7
N1—C2—S1	118.6 (2)	C10—C9—H9B	109.7
C4—C3—O2	110.1 (3)	C8—C9—H9B	109.7
C4—C3—C1	130.1 (3)	H9A—C9—H9B	108.2
O2—C3—C1	119.8 (3)	C11—C10—C9	111.2 (3)
C3—C4—C5	105.9 (3)	C11—C10—H10A	109.4
C3—C4—H4	127	C9—C10—H10A	109.4
C5—C4—H4	127	C11—C10—H10B	109.4
C6—C5—C4	107.1 (3)	C9—C10—H10B	109.4
C6—C5—H5	126.5	H10A—C10—H10B	108
C4—C5—H5	126.5	N2—C11—C10	110.7 (3)
C5—C6—O2	111.0 (3)	N2—C11—H11A	109.5
C5—C6—H6	124.5	C10—C11—H11A	109.5
O2—C6—H6	124.5	N2—C11—H11B	109.5
N2—C7—C8	110.0 (3)	C10—C11—H11B	109.5
N2—C7—H7A	109.7	H11A—C11—H11B	108.1
C8—C7—H7A	109.7	C1—N1—C2	123.2 (3)
N2—C7—H7B	109.7	C1—N1—H1	118.4
C8—C7—H7B	109.7	C2—N1—H1	118.4
H7A—C7—H7B	108.2	C2—N2—C11	121.6 (3)
C7—C8—C9	112.2 (4)	C2—N2—C7	125.4 (3)
C7—C8—H8A	109.2	C11—N2—C7	113.0 (3)
C9—C8—H8A	109.2	C6—O2—C3	105.9 (3)
C7—C8—H8B	109.2
O1—C1—C3—C4	−5.9 (5)	N2—C2—N1—C1	59.9 (4)
N1—C1—C3—C4	172.5 (3)	S1—C2—N1—C1	−121.4 (3)
O1—C1—C3—O2	176.5 (3)	N1—C2—N2—C11	−173.8 (3)
N1—C1—C3—O2	−5.2 (4)	S1—C2—N2—C11	7.6 (5)
O2—C3—C4—C5	−0.2 (4)	N1—C2—N2—C7	7.8 (4)
C1—C3—C4—C5	−178.0 (3)	S1—C2—N2—C7	−170.8 (3)
C3—C4—C5—C6	−0.5 (5)	C10—C11—N2—C2	−120.6 (4)
C4—C5—C6—O2	1.0 (5)	C10—C11—N2—C7	58.1 (4)
N2—C7—C8—C9	54.0 (5)	C8—C7—N2—C2	122.3 (4)
C7—C8—C9—C10	−53.7 (5)	C8—C7—N2—C11	−56.3 (4)
C8—C9—C10—C11	54.5 (5)	C5—C6—O2—C3	−1.1 (5)
C9—C10—C11—N2	−56.8 (5)	C4—C3—O2—C6	0.8 (4)
O1—C1—N1—C2	−0.1 (5)	C1—C3—O2—C6	178.8 (3)
C3—C1—N1—C2	−178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.38	2.756 (3)	107
N1—H1···O1i	0.86	2.18	2.994 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.38	2.756 (3)	107
N1—H1⋯O1i	0.86	2.18	2.994 (4)	157

Symmetry code: (i) .