1-(3-Cyano-phen-yl)-3-(2-furo-yl)thio-urea.

The title compound, C(13)H(9)N(3)O(2)S, was synthesized from furoyl isothio-cyanate and 3-amino-benzonitrile in dry acetone. The thio-urea group is in the thio-amide form. The thio-urea fragment makes dihedral angles of 3.91 (16) and 37.83 (12)° with the ketofuran group and the benzene ring, respectively. The mol-ecular geometry is stabilized by N-H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related mol-ecules are linked by two inter-molecular N-H⋯S hydrogen bonds to form dimers.

Related literature

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

Experimental

Crystal data

C13H9N3O2S

M = 271.29

Monoclinic,

a = 16.7375 (5) Å

b = 3.8789 (1) Å

c = 19.6739 (5) Å

β = 96.956 (1)°

V = 1267.89 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.16 × 0.04 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

4807 measured reflections

2684 independent reflections

1908 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.208

S = 1.08

2684 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.34 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/S1600536808016012/rz2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016012/rz2219Isup2.hkl

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

C13H9N3O2S	F000 = 560
Mr = 271.29	Dx = 1.421 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3051 reflections
a = 16.7375 (5) Å	θ = 2.9–26.7º
b = 3.87890 (10) Å	µ = 0.26 mm−1
c = 19.6739 (5) Å	T = 294 K
β = 96.9560 (10)º	Prism, colourless
V = 1267.89 (6) Å3	0.16 × 0.04 × 0.03 mm
Z = 4

Enraf–Nonius KappaCCD diffractometer	Rint = 0.040
CCD rotation images, thick slices scans	θmax = 26.9º
Absorption correction: none	θmin = 3.9º
4807 measured reflections	h = −20→21
2684 independent reflections	k = −4→4
1908 reflections with I > 2σ(I)	l = −25→24

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0641P)2 + 3.4802P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.071	(Δ/σ)max < 0.001
wR(F2) = 0.208	Δρmax = 0.51 e Å−3
S = 1.08	Δρmin = −0.34 e Å−3
2684 reflections	Extinction correction: none
172 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	0.10993 (6)	0.7197 (3)	−0.00840 (5)	0.0465 (3)
O1	0.08926 (19)	0.9883 (11)	0.21366 (15)	0.0699 (11)
C13	0.3735 (3)	1.3099 (15)	−0.0369 (3)	0.0617 (13)
N3	0.3872 (3)	1.4227 (17)	−0.0884 (3)	0.0909 (17)
N1	0.0452 (2)	0.7949 (10)	0.10538 (16)	0.0457 (9)
H1	0.0031	0.7186	0.0805	0.055*
O2	−0.10121 (19)	0.6665 (10)	0.14431 (15)	0.0643 (10)
N2	0.17909 (19)	0.9396 (11)	0.11374 (17)	0.0482 (9)
H2	0.1712	0.991	0.1549	0.058*
C7	0.2586 (2)	0.9846 (11)	0.0976 (2)	0.0415 (9)
C5	−0.1517 (3)	0.7102 (15)	0.2424 (3)	0.0676 (15)
H5	−0.1872	0.6986	0.2752	0.081*
C2	0.1143 (2)	0.8261 (11)	0.07249 (19)	0.0398 (9)
C9	0.3556 (2)	1.1694 (12)	0.0263 (2)	0.0474 (10)
C8	0.2756 (2)	1.1209 (12)	0.0366 (2)	0.0456 (10)
H8	0.2342	1.1798	0.0026	0.055*
C3	−0.0430 (2)	0.7960 (12)	0.1925 (2)	0.0471 (10)
C10	0.4180 (3)	1.0819 (14)	0.0767 (2)	0.0571 (12)
H10	0.4714	1.1093	0.069	0.068*
C1	0.0355 (3)	0.8694 (13)	0.1719 (2)	0.0495 (11)
C11	0.3993 (3)	0.9541 (15)	0.1381 (3)	0.0633 (14)
H11	0.4403	0.9026	0.1729	0.076*
C4	−0.0724 (3)	0.8274 (14)	0.2531 (2)	0.0581 (13)
H4	−0.0452	0.9105	0.2938	0.07*
C6	−0.1676 (3)	0.6183 (17)	0.1772 (3)	0.0705 (15)
H6	−0.2168	0.5335	0.1569	0.085*
C12	0.3204 (3)	0.9022 (13)	0.1483 (2)	0.0535 (11)
H12	0.3084	0.8109	0.1895	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.0410 (6)	0.0603 (8)	0.0382 (5)	−0.0046 (5)	0.0050 (4)	−0.0056 (5)
O1	0.0528 (19)	0.112 (3)	0.0457 (17)	−0.021 (2)	0.0093 (14)	−0.0222 (19)
C13	0.049 (3)	0.074 (4)	0.063 (3)	−0.004 (2)	0.015 (2)	0.004 (3)
N3	0.088 (4)	0.115 (5)	0.073 (3)	−0.013 (3)	0.025 (3)	0.017 (3)
N1	0.0389 (17)	0.061 (2)	0.0367 (17)	−0.0055 (17)	0.0040 (14)	−0.0029 (17)
O2	0.0536 (18)	0.096 (3)	0.0440 (16)	−0.0177 (19)	0.0072 (14)	−0.0081 (18)
N2	0.0393 (18)	0.069 (3)	0.0355 (17)	−0.0083 (18)	0.0028 (13)	−0.0001 (17)
C7	0.039 (2)	0.041 (2)	0.045 (2)	−0.0045 (18)	0.0045 (16)	0.0001 (18)
C5	0.058 (3)	0.075 (4)	0.075 (3)	0.001 (3)	0.031 (3)	−0.004 (3)
C2	0.0358 (19)	0.043 (2)	0.040 (2)	−0.0019 (17)	0.0049 (16)	0.0019 (18)
C9	0.044 (2)	0.046 (3)	0.053 (2)	−0.0032 (19)	0.0071 (18)	0.003 (2)
C8	0.039 (2)	0.052 (3)	0.044 (2)	−0.0024 (19)	0.0022 (17)	0.0050 (19)
C3	0.042 (2)	0.058 (3)	0.042 (2)	−0.004 (2)	0.0073 (17)	−0.003 (2)
C10	0.036 (2)	0.071 (3)	0.064 (3)	−0.005 (2)	0.005 (2)	0.002 (3)
C1	0.047 (2)	0.060 (3)	0.042 (2)	−0.005 (2)	0.0072 (18)	−0.001 (2)
C11	0.043 (2)	0.081 (4)	0.062 (3)	−0.001 (2)	−0.011 (2)	0.010 (3)
C4	0.059 (3)	0.073 (4)	0.045 (2)	−0.003 (3)	0.016 (2)	−0.009 (2)
C6	0.045 (3)	0.094 (4)	0.073 (3)	−0.014 (3)	0.013 (2)	0.009 (3)
C12	0.051 (2)	0.060 (3)	0.047 (2)	−0.008 (2)	−0.0041 (19)	0.006 (2)

S1—C2	1.637 (4)	C5—C4	1.395 (7)
O1—C1	1.233 (5)	C5—H5	0.93
C13—N3	1.153 (6)	C9—C8	1.392 (6)
C13—C9	1.422 (6)	C9—C10	1.392 (6)
N1—C1	1.368 (5)	C8—H8	0.93
N1—C2	1.397 (5)	C3—C4	1.348 (6)
N1—H1	0.86	C3—C1	1.450 (6)
O2—C6	1.365 (6)	C10—C11	1.377 (7)
O2—C3	1.369 (5)	C10—H10	0.93
N2—C2	1.348 (5)	C11—C12	1.375 (6)
N2—C7	1.416 (5)	C11—H11	0.93
N2—H2	0.86	C4—H4	0.93
C7—C8	1.373 (6)	C6—H6	0.93
C7—C12	1.383 (6)	C12—H12	0.93
C5—C6	1.326 (7)
N3—C13—C9	179.3 (6)	C9—C8—H8	120.5
C1—N1—C2	128.7 (3)	C4—C3—O2	109.9 (4)
C1—N1—H1	115.6	C4—C3—C1	132.0 (4)
C2—N1—H1	115.6	O2—C3—C1	118.1 (4)
C6—O2—C3	105.9 (4)	C11—C10—C9	118.9 (4)
C2—N2—C7	128.0 (3)	C11—C10—H10	120.6
C2—N2—H2	116	C9—C10—H10	120.6
C7—N2—H2	116	O1—C1—N1	123.7 (4)
C8—C7—C12	120.2 (4)	O1—C1—C3	120.0 (4)
C8—C7—N2	122.9 (4)	N1—C1—C3	116.3 (4)
C12—C7—N2	116.8 (4)	C12—C11—C10	120.3 (4)
C6—C5—C4	108.0 (4)	C12—C11—H11	119.9
C6—C5—H5	126	C10—C11—H11	119.9
C4—C5—H5	126	C3—C4—C5	106.3 (4)
N2—C2—N1	113.6 (3)	C3—C4—H4	126.9
N2—C2—S1	127.3 (3)	C5—C4—H4	126.9
N1—C2—S1	119.1 (3)	C5—C6—O2	110.0 (4)
C8—C9—C10	121.1 (4)	C5—C6—H6	125
C8—C9—C13	119.1 (4)	O2—C6—H6	125
C10—C9—C13	119.8 (4)	C11—C12—C7	120.6 (4)
C7—C8—C9	118.9 (4)	C11—C12—H12	119.7
C7—C8—H8	120.5	C7—C12—H12	119.7
C2—N2—C7—C8	41.1 (7)	C2—N1—C1—C3	−177.3 (4)
C2—N2—C7—C12	−142.4 (5)	C4—C3—C1—O1	−1.2 (9)
C7—N2—C2—N1	176.9 (4)	O2—C3—C1—O1	179.5 (5)
C7—N2—C2—S1	−1.9 (7)	C4—C3—C1—N1	177.9 (5)
C1—N1—C2—N2	1.3 (7)	O2—C3—C1—N1	−1.3 (7)
C1—N1—C2—S1	−179.8 (4)	C9—C10—C11—C12	2.4 (8)
C12—C7—C8—C9	0.9 (7)	O2—C3—C4—C5	0.5 (6)
N2—C7—C8—C9	177.3 (4)	C1—C3—C4—C5	−178.8 (5)
C10—C9—C8—C7	0.1 (7)	C6—C5—C4—C3	−0.7 (7)
C13—C9—C8—C7	179.9 (5)	C4—C5—C6—O2	0.7 (7)
C6—O2—C3—C4	−0.1 (6)	C3—O2—C6—C5	−0.4 (6)
C6—O2—C3—C1	179.3 (5)	C10—C11—C12—C7	−1.5 (8)
C8—C9—C10—C11	−1.7 (8)	C8—C7—C12—C11	−0.3 (7)
C13—C9—C10—C11	178.4 (5)	N2—C7—C12—C11	−176.8 (5)
C2—N1—C1—O1	1.8 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.28	2.701 (5)	110
N1—H1···S1i	0.86	2.80	3.629 (4)	163
N2—H2···O1	0.86	1.90	2.622 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.28	2.701 (5)	110
N1—H1⋯S1i	0.86	2.80	3.629 (4)	163
N2—H2⋯O1	0.86	1.90	2.622 (4)	141

Symmetry code: (i) .