1-(2-Furo-yl)-3-(o-tol-yl)thio-urea.

The title compound, C(13)H(12)N(2)O(2)S, was synthesized from furoyl isothio-cyanate and o-toluidine in dry acetone. The thio-urea group is in the thio-amide form. The central thio-urea fragment makes dihedral angles of 2.6 (1) and 22.4 (1)° with the ketofuran group and the benzene ring, respectively. The mol-ecular structure is stabilized by N-H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related mol-ecules are linked by a pair of N-H⋯S hydrogen bonds to form a dimer with an R(2) (2)(6) ring motif.

Related literature

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

Experimental

Crystal data

C13H12N2O2S

M = 260.31

Monoclinic,

a = 6.0976 (1) Å

b = 16.6689 (6) Å

c = 13.1462 (4) Å

β = 108.765 (2)°

V = 1265.16 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 294 K

0.50 × 0.08 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian (Coppens et al., 1965 ▶) T min = 0.925, T max = 0.983

8242 measured reflections

2408 independent reflections

1594 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.02

2408 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (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/S1600536808020114/ci2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020114/ci2623Isup2.hkl

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

C13H12N2O2S	F000 = 544
Mr = 260.31	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20621 reflections
a = 6.0976 (1) Å	θ = 2.9–25.7º
b = 16.6689 (6) Å	µ = 0.25 mm−1
c = 13.1462 (4) Å	T = 294 K
β = 108.765 (2)º	Needle, colourless
V = 1265.16 (6) Å3	0.50 × 0.08 × 0.07 mm
Z = 4

Nonius KappaCCD diffractometer	Rint = 0.048
ω scans	θmax = 25.7º
Absorption correction: Gaussian(Coppens et al., 1965)	θmin = 2.9º
Tmin = 0.925, Tmax = 0.983	h = −6→7
8242 measured reflections	k = −19→20
2408 independent reflections	l = −16→16
1594 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.1015P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046	(Δ/σ)max < 0.001
wR(F2) = 0.130	Δρmax = 0.26 e Å−3
S = 1.03	Δρmin = −0.30 e Å−3
2408 reflections	Extinction correction: none
164 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	0.22254 (12)	0.09680 (4)	0.04759 (5)	0.0800 (3)
N2	0.4198 (3)	0.09229 (10)	0.26210 (13)	0.0561 (4)
H2	0.408	0.0712	0.3198	0.067*
O2	−0.2979 (3)	−0.06394 (9)	0.17467 (12)	0.0679 (4)
O1	0.1899 (3)	0.01628 (10)	0.37313 (12)	0.0757 (5)
N1	0.0880 (3)	0.01904 (10)	0.18967 (13)	0.0578 (5)
H1	−0.0083	−0.0016	0.1328	0.069*
C7	0.6105 (3)	0.14441 (12)	0.27881 (15)	0.0528 (5)
C2	0.2552 (4)	0.07008 (12)	0.17262 (17)	0.0556 (5)
C1	0.0568 (4)	−0.00258 (13)	0.28515 (17)	0.0587 (5)
C12	0.7138 (4)	0.16151 (13)	0.20141 (17)	0.0631 (6)
H12	0.6557	0.1389	0.1333	0.076*
C3	−0.1472 (4)	−0.05056 (13)	0.27543 (17)	0.0594 (5)
C8	0.7009 (4)	0.17683 (13)	0.38190 (17)	0.0609 (6)
C9	0.8905 (4)	0.22716 (14)	0.40236 (19)	0.0728 (6)
H9	0.9524	0.2494	0.4705	0.087*
C4	−0.2232 (5)	−0.08806 (15)	0.3482 (2)	0.0774 (7)
H4	−0.1528	−0.0881	0.4224	0.093*
C10	0.9905 (4)	0.24531 (14)	0.3252 (2)	0.0737 (6)
H10	1.1166	0.2799	0.3409	0.088*
C11	0.9035 (4)	0.21225 (14)	0.2256 (2)	0.0703 (6)
H11	0.9719	0.2238	0.1734	0.084*
C13	0.5994 (4)	0.15856 (18)	0.46916 (17)	0.0835 (8)
H13A	0.671	0.1921	0.5303	0.125*
H13B	0.6264	0.1032	0.4896	0.125*
H13C	0.4357	0.1687	0.4435	0.125*
C6	−0.4688 (4)	−0.11084 (14)	0.1874 (2)	0.0769 (7)
H6	−0.5959	−0.1291	0.1316	0.092*
C5	−0.4295 (5)	−0.12709 (15)	0.2904 (2)	0.0831 (8)
H5	−0.5214	−0.1585	0.319	0.1*

	U11	U22	U33	U12	U13	U23
S1	0.0983 (5)	0.0930 (5)	0.0458 (4)	−0.0272 (4)	0.0189 (3)	0.0060 (3)
N2	0.0625 (10)	0.0623 (10)	0.0453 (10)	−0.0051 (9)	0.0199 (9)	0.0046 (8)
O2	0.0709 (10)	0.0737 (10)	0.0649 (10)	−0.0096 (8)	0.0302 (8)	−0.0045 (7)
O1	0.0788 (10)	0.0981 (13)	0.0498 (9)	−0.0183 (9)	0.0201 (8)	0.0072 (8)
N1	0.0627 (10)	0.0649 (11)	0.0469 (9)	−0.0066 (9)	0.0192 (8)	0.0012 (8)
C7	0.0572 (11)	0.0511 (12)	0.0512 (12)	0.0023 (10)	0.0190 (9)	0.0062 (9)
C2	0.0664 (13)	0.0525 (12)	0.0508 (13)	−0.0005 (10)	0.0231 (11)	0.0011 (9)
C1	0.0652 (13)	0.0602 (13)	0.0542 (13)	0.0000 (11)	0.0240 (11)	0.0040 (10)
C12	0.0688 (13)	0.0661 (14)	0.0583 (13)	0.0001 (11)	0.0262 (11)	0.0032 (10)
C3	0.0642 (13)	0.0624 (14)	0.0553 (13)	0.0021 (11)	0.0245 (11)	0.0016 (10)
C8	0.0639 (13)	0.0641 (14)	0.0541 (13)	−0.0005 (11)	0.0184 (10)	0.0032 (10)
C9	0.0739 (14)	0.0746 (16)	0.0652 (15)	−0.0132 (12)	0.0158 (12)	−0.0037 (12)
C4	0.0832 (17)	0.0879 (17)	0.0700 (16)	−0.0091 (14)	0.0370 (14)	0.0092 (13)
C10	0.0684 (14)	0.0705 (16)	0.0810 (17)	−0.0085 (12)	0.0223 (13)	0.0066 (13)
C11	0.0675 (14)	0.0750 (15)	0.0765 (17)	0.0015 (12)	0.0343 (13)	0.0164 (13)
C13	0.0874 (17)	0.113 (2)	0.0507 (13)	−0.0239 (15)	0.0226 (12)	−0.0079 (13)
C6	0.0716 (15)	0.0789 (17)	0.0887 (19)	−0.0192 (13)	0.0376 (14)	−0.0161 (14)
C5	0.0880 (18)	0.0825 (18)	0.094 (2)	−0.0170 (14)	0.0506 (16)	0.0027 (15)

S1—C2	1.652 (2)	C8—C9	1.383 (3)
N2—C2	1.330 (3)	C8—C13	1.500 (3)
N2—C7	1.411 (2)	C9—C10	1.375 (3)
N2—H2	0.86	C9—H9	0.93
O2—C6	1.355 (3)	C4—C5	1.403 (4)
O2—C3	1.366 (3)	C4—H4	0.93
O1—C1	1.221 (2)	C10—C11	1.361 (3)
N1—C1	1.377 (2)	C10—H10	0.93
N1—C2	1.400 (3)	C11—H11	0.93
N1—H1	0.86	C13—H13A	0.96
C7—C12	1.388 (3)	C13—H13B	0.96
C7—C8	1.397 (3)	C13—H13C	0.96
C1—C3	1.449 (3)	C6—C5	1.325 (4)
C12—C11	1.385 (3)	C6—H6	0.93
C12—H12	0.93	C5—H5	0.93
C3—C4	1.344 (3)
C2—N2—C7	131.21 (17)	C10—C9—C8	122.1 (2)
C2—N2—H2	114.4	C10—C9—H9	118.9
C7—N2—H2	114.4	C8—C9—H9	118.9
C6—O2—C3	106.19 (18)	C3—C4—C5	106.5 (2)
C1—N1—C2	128.76 (18)	C3—C4—H4	126.7
C1—N1—H1	115.6	C5—C4—H4	126.7
C2—N1—H1	115.6	C11—C10—C9	119.5 (2)
C12—C7—C8	120.07 (19)	C11—C10—H10	120.2
C12—C7—N2	123.93 (19)	C9—C10—H10	120.2
C8—C7—N2	115.95 (17)	C10—C11—C12	120.4 (2)
N2—C2—N1	114.13 (17)	C10—C11—H11	119.8
N2—C2—S1	128.33 (16)	C12—C11—H11	119.8
N1—C2—S1	117.52 (16)	C8—C13—H13A	109.5
O1—C1—N1	123.5 (2)	C8—C13—H13B	109.5
O1—C1—C3	121.03 (19)	H13A—C13—H13B	109.5
N1—C1—C3	115.5 (2)	C8—C13—H13C	109.5
C11—C12—C7	120.0 (2)	H13A—C13—H13C	109.5
C11—C12—H12	120	H13B—C13—H13C	109.5
C7—C12—H12	120	C5—C6—O2	110.5 (2)
C4—C3—O2	109.6 (2)	C5—C6—H6	124.7
C4—C3—C1	132.6 (2)	O2—C6—H6	124.7
O2—C3—C1	117.80 (18)	C6—C5—C4	107.1 (2)
C9—C8—C7	117.88 (19)	C6—C5—H5	126.4
C9—C8—C13	120.0 (2)	C4—C5—H5	126.4
C7—C8—C13	122.15 (19)
C2—N2—C7—C12	−24.6 (3)	N1—C1—C3—O2	−5.5 (3)
C2—N2—C7—C8	158.1 (2)	C12—C7—C8—C9	1.5 (3)
C7—N2—C2—N1	−177.53 (18)	N2—C7—C8—C9	178.90 (19)
C7—N2—C2—S1	0.8 (3)	C12—C7—C8—C13	−178.4 (2)
C1—N1—C2—N2	8.7 (3)	N2—C7—C8—C13	−1.0 (3)
C1—N1—C2—S1	−169.87 (17)	C7—C8—C9—C10	−0.3 (3)
C2—N1—C1—O1	−6.2 (4)	C13—C8—C9—C10	179.6 (2)
C2—N1—C1—C3	174.14 (18)	O2—C3—C4—C5	0.5 (3)
C8—C7—C12—C11	−1.5 (3)	C1—C3—C4—C5	−178.3 (2)
N2—C7—C12—C11	−178.73 (18)	C8—C9—C10—C11	−0.9 (4)
C6—O2—C3—C4	−0.1 (2)	C9—C10—C11—C12	0.9 (4)
C6—O2—C3—C1	178.91 (18)	C7—C12—C11—C10	0.3 (3)
O1—C1—C3—C4	−6.4 (4)	C3—O2—C6—C5	−0.3 (3)
N1—C1—C3—C4	173.3 (2)	O2—C6—C5—C4	0.6 (3)
O1—C1—C3—O2	174.84 (19)	C3—C4—C5—C6	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.26	2.682 (3)	110
N1—H1···S1i	0.86	2.80	3.639 (2)	165
N2—H2···O1	0.86	1.92	2.649 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.26	2.682 (3)	110
N1—H1⋯S1i	0.86	2.80	3.639 (2)	165
N2—H2⋯O1	0.86	1.92	2.649 (2)	141

Symmetry code: (i) .