1-Furfuryl-3-furoylthio-urea.

The title compound, C(11)H(10)N(2)O(3)S, was synthesized from furoyl isothio-cyanate and furfurylamine in dry acetone. The thio-urea group is in the thio-amide form. The trans-cis geometry of the thio-urea group is stabilized by intra-molecular hydrogen bonding between the carbonyl and cis-thio-amide and results in a pseudo-S(6) planar ring which makes dihedral angles of 2.5 (3) and 88.1 (2)° with the furoyl and furfuryl groups, respectively. There is also an intra-molecular hydrogen bond between the furan O atom and the other thio-amide H atom. In the crystal structure, mol-ecules are linked by two inter-molecular N-H⋯O hydrogen bonds, forming dimers. These dimers are stacked within the crystal structure along the [010] direction.

Related literature

For general background, see: Dhooghe et al. (2005 ▶); Aly et al. (2007 ▶); Estévez-Hernández et al. (2007 ▶). For related structures, see: Koch (2001 ▶); Yamin & Hassan (2004 ▶). For the synthesis, see: Otazo et al. (2001 ▶).

Experimental

Crystal data

C11H10N2O3S

M = 250.27

Triclinic,

a = 4.5999 (2) Å

b = 11.3792 (6) Å

c = 12.0556 (5) Å

α = 68.351 (3)°

β = 83.187 (4)°

γ = 89.367 (3)°

V = 582.01 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 294 K

0.16 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

4433 measured reflections

2427 independent reflections

1753 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.05

2427 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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/S1600536808015250/xu2426sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015250/xu2426Isup2.hkl

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

C11H10N2O3S	Z = 2
Mr = 250.27	F000 = 260
Triclinic, P1	Dx = 1.428 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.5999 (2) Å	Cell parameters from 2356 reflections
b = 11.3792 (6) Å	θ = 2.9–26.7º
c = 12.0556 (5) Å	µ = 0.28 mm−1
α = 68.351 (3)º	T = 294 K
β = 83.187 (4)º	Prism, colourless
γ = 89.367 (3)º	0.16 × 0.15 × 0.08 mm
V = 582.01 (5) Å3

Nonius KappaCCD diffractometer	Rint = 0.028
ω scans	θmax = 26.6º
Absorption correction: none	θmin = 3.1º
4433 measured reflections	h = −5→5
2427 independent reflections	k = −14→14
1753 reflections with I > 2σ(I)	l = −15→13

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.1199P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.048	(Δ/σ)max < 0.001
wR(F2) = 0.135	Δρmax = 0.32 e Å−3
S = 1.05	Δρmin = −0.28 e Å−3
2427 reflections	Extinction correction: none
154 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
S1	−0.16463 (15)	0.45844 (5)	0.35901 (6)	0.0578 (2)
O1	0.1719 (4)	0.07028 (14)	0.56626 (15)	0.0540 (4)
O2	0.4479 (4)	0.28509 (15)	0.68097 (15)	0.0565 (4)
N2	−0.1523 (4)	0.21274 (16)	0.39894 (15)	0.0417 (4)
H2	−0.0911	0.139	0.4381	0.05*
O3	0.0164 (5)	0.1731 (2)	0.16872 (17)	0.0793 (6)
N1	0.1109 (4)	0.28290 (16)	0.51574 (15)	0.0421 (4)
H1	0.1601	0.3461	0.5332	0.05*
C8	−0.1860 (5)	0.2555 (2)	0.1856 (2)	0.0476 (5)
C7	−0.3440 (5)	0.2252 (2)	0.30733 (19)	0.0461 (5)
H7A	−0.4809	0.2911	0.3054	0.055*
H7B	−0.4567	0.1465	0.3299	0.055*
C3	0.3974 (5)	0.17197 (19)	0.67285 (18)	0.0415 (5)
C1	0.2185 (5)	0.16912 (19)	0.58107 (18)	0.0411 (5)
C2	−0.0679 (5)	0.30996 (19)	0.42464 (18)	0.0396 (5)
C4	0.5302 (6)	0.0818 (2)	0.7549 (2)	0.0606 (7)
H4	0.5303	−0.004	0.7676	0.073*
C9	−0.2028 (7)	0.3500 (3)	0.0816 (3)	0.0771 (9)
H9	−0.3219	0.4193	0.068	0.092*
C6	0.6146 (6)	0.2632 (3)	0.7713 (2)	0.0611 (7)
H6	0.6806	0.325	0.7966	0.073*
C5	0.6702 (6)	0.1424 (3)	0.8184 (2)	0.0607 (7)
H5	0.7805	0.1043	0.8814	0.073*
C10	0.0005 (8)	0.3236 (4)	−0.0059 (3)	0.0850 (10)
H10	0.0366	0.3725	−0.0875	0.102*
C11	0.1238 (8)	0.2192 (4)	0.0502 (3)	0.0893 (10)
H11	0.2657	0.1811	0.0144	0.107*

	U11	U22	U33	U12	U13	U23
S1	0.0793 (5)	0.0362 (3)	0.0594 (4)	0.0082 (3)	−0.0299 (3)	−0.0131 (3)
O1	0.0709 (11)	0.0387 (8)	0.0580 (10)	0.0093 (7)	−0.0252 (8)	−0.0195 (7)
O2	0.0688 (11)	0.0463 (9)	0.0608 (10)	0.0043 (8)	−0.0235 (8)	−0.0225 (8)
N2	0.0499 (10)	0.0363 (9)	0.0390 (9)	0.0019 (7)	−0.0114 (8)	−0.0122 (7)
O3	0.0938 (15)	0.0759 (13)	0.0589 (12)	0.0162 (11)	0.0080 (10)	−0.0197 (10)
N1	0.0512 (10)	0.0335 (8)	0.0426 (9)	0.0010 (7)	−0.0137 (8)	−0.0128 (7)
C8	0.0536 (13)	0.0444 (12)	0.0467 (12)	−0.0013 (10)	−0.0165 (10)	−0.0158 (10)
C7	0.0458 (12)	0.0479 (12)	0.0472 (12)	0.0008 (9)	−0.0131 (10)	−0.0185 (10)
C3	0.0437 (11)	0.0406 (11)	0.0420 (11)	0.0019 (9)	−0.0077 (9)	−0.0167 (9)
C1	0.0428 (11)	0.0400 (11)	0.0384 (11)	0.0012 (9)	−0.0034 (9)	−0.0125 (9)
C2	0.0413 (11)	0.0399 (11)	0.0350 (10)	0.0013 (9)	−0.0052 (8)	−0.0107 (9)
C4	0.0782 (17)	0.0469 (13)	0.0612 (15)	0.0147 (12)	−0.0309 (13)	−0.0189 (11)
C9	0.098 (2)	0.0648 (17)	0.0581 (17)	−0.0002 (16)	−0.0300 (16)	−0.0041 (14)
C6	0.0649 (16)	0.0689 (17)	0.0599 (15)	−0.0010 (13)	−0.0212 (13)	−0.0317 (13)
C5	0.0655 (16)	0.0704 (17)	0.0512 (14)	0.0123 (13)	−0.0272 (12)	−0.0229 (12)
C10	0.102 (2)	0.106 (3)	0.0390 (15)	−0.034 (2)	−0.0080 (15)	−0.0166 (16)
C11	0.108 (3)	0.098 (3)	0.0561 (19)	−0.010 (2)	0.0174 (18)	−0.0309 (19)

S1—C2	1.661 (2)	C7—H7A	0.97
O1—C1	1.227 (2)	C7—H7B	0.97
O2—C3	1.351 (3)	C3—C4	1.336 (3)
O2—C6	1.353 (3)	C3—C1	1.465 (3)
N2—C2	1.327 (3)	C4—C5	1.412 (4)
N2—C7	1.460 (3)	C4—H4	0.93
N2—H2	0.86	C9—C10	1.439 (5)
O3—C11	1.359 (3)	C9—H9	0.93
O3—C8	1.366 (3)	C6—C5	1.314 (4)
N1—C1	1.367 (3)	C6—H6	0.93
N1—C2	1.392 (3)	C5—H5	0.93
N1—H1	0.86	C10—C11	1.294 (5)
C8—C9	1.327 (3)	C10—H10	0.93
C8—C7	1.476 (3)	C11—H11	0.93
C3—O2—C6	106.57 (19)	N1—C1—C3	115.07 (18)
C2—N2—C7	123.03 (18)	N2—C2—N1	116.40 (17)
C2—N2—H2	118.5	N2—C2—S1	125.21 (16)
C7—N2—H2	118.5	N1—C2—S1	118.38 (15)
C11—O3—C8	107.1 (2)	C3—C4—C5	106.4 (2)
C1—N1—C2	128.53 (18)	C3—C4—H4	126.8
C1—N1—H1	115.7	C5—C4—H4	126.8
C2—N1—H1	115.7	C8—C9—C10	106.1 (3)
C9—C8—O3	109.2 (2)	C8—C9—H9	126.9
C9—C8—C7	132.7 (3)	C10—C9—H9	126.9
O3—C8—C7	118.09 (19)	C5—C6—O2	110.6 (2)
N2—C7—C8	113.74 (18)	C5—C6—H6	124.7
N2—C7—H7A	108.8	O2—C6—H6	124.7
C8—C7—H7A	108.8	C6—C5—C4	106.7 (2)
N2—C7—H7B	108.8	C6—C5—H5	126.6
C8—C7—H7B	108.8	C4—C5—H5	126.6
H7A—C7—H7B	107.7	C11—C10—C9	107.2 (3)
C4—C3—O2	109.73 (19)	C11—C10—H10	126.4
C4—C3—C1	132.6 (2)	C9—C10—H10	126.4
O2—C3—C1	117.69 (18)	C10—C11—O3	110.3 (3)
O1—C1—N1	123.86 (19)	C10—C11—H11	124.8
O1—C1—C3	121.08 (19)	O3—C11—H11	124.8
C11—O3—C8—C9	−0.4 (3)	C7—N2—C2—S1	0.2 (3)
C11—O3—C8—C7	178.2 (2)	C1—N1—C2—N2	1.8 (3)
C2—N2—C7—C8	88.1 (2)	C1—N1—C2—S1	−179.47 (17)
C9—C8—C7—N2	−122.7 (3)	O2—C3—C4—C5	0.4 (3)
O3—C8—C7—N2	59.2 (3)	C1—C3—C4—C5	−179.9 (2)
C6—O2—C3—C4	−0.5 (3)	O3—C8—C9—C10	0.7 (3)
C6—O2—C3—C1	179.72 (19)	C7—C8—C9—C10	−177.6 (2)
C2—N1—C1—O1	0.9 (4)	C3—O2—C6—C5	0.4 (3)
C2—N1—C1—C3	−178.86 (19)	O2—C6—C5—C4	−0.2 (3)
C4—C3—C1—O1	−2.1 (4)	C3—C4—C5—C6	−0.1 (3)
O2—C3—C1—O1	177.7 (2)	C8—C9—C10—C11	−0.7 (3)
C4—C3—C1—N1	177.7 (2)	C9—C10—C11—O3	0.5 (4)
O2—C3—C1—N1	−2.5 (3)	C8—O3—C11—C10	−0.1 (4)
C7—N2—C2—N1	178.88 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.24	2.672 (3)	111
N2—H2···O1	0.86	2.00	2.677 (3)	135
N2—H2···O1i	0.86	2.43	3.091 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.24	2.672 (3)	111
N2—H2⋯O1	0.86	2.00	2.677 (3)	135
N2—H2⋯O1i	0.86	2.43	3.091 (3)	133

Symmetry code: (i) .