1-Benzyl-3-(2-furo-yl)thio-urea.

In the title compound, C(13)H(12)N(2)O(2)S, the dihedral angle between the two aromatic ring planes is 87.52 (12)°. The mol-ecule shows an intra-molecular N-H⋯O hydrogen bond. The crystal structure is stabilized by inter-molecular N-H⋯S and C-H⋯O hydrogen bonding.

Related literature

For general background, see: Estévez-Hernández et al. (2007 ▶); Otazo et al. (2001 ▶). For related structures, see: Arslan et al. (2004 ▶); Khawar Rauf et al. (2007 ▶). For the synthesis, see: Otazo et al. (2001 ▶).

Experimental

Crystal data

C13H12N2O2S

M = 260.31

Tetragonal,

a = 9.445 (3) Å

c = 27.107 (6) Å

V = 2418.2 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 150 (2) K

0.3 × 0.1 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

12492 measured reflections

2120 independent reflections

1922 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.06

2120 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 802 Friedel pairs

Flack parameter: −0.16 (10)

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/S1600536808006181/xu2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006181/xu2401Isup2.hkl

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

C13H12N2O2S	Z = 8
Mr = 260.31	F000 = 1088
Tetragonal, P41212	Dx = 1.43 Mg m−3
Hall symbol: P 4abw 2nw	Melting point: 402.5 K
a = 9.445 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.445 (3) Å	Cell parameters from 9761 reflections
c = 27.107 (6) Å	θ = 2.9–26.0º
α = 90º	µ = 0.26 mm−1
β = 90º	T = 150 (2) K
γ = 90º	Block, colourless
V = 2418.2 (12) Å3	0.3 × 0.1 × 0.08 mm

Nonius KappaCCD diffractometer	Rint = 0.092
ω scans	θmax = 25.0º
Absorption correction: none	θmin = 3.7º
12492 measured reflections	h = −11→9
2120 independent reflections	k = −8→11
1922 reflections with I > 2σ(I)	l = −32→24

Refinement on F2	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.4478P] where P = (Fo2 + 2Fc2)/3
Least-squares matrix: full	(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.035	Δρmax = 0.17 e Å−3
wR(F2) = 0.085	Δρmin = −0.19 e Å−3
S = 1.06	Extinction correction: none
2120 reflections	Absolute structure: Flack (1983), 802 Friedel pairs
163 parameters	Flack parameter: −0.16 (10)
H-atom parameters constrained

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	0.7270 (2)	0.4402 (2)	0.16180 (8)	0.0311 (6)
H1A	0.7104	0.3494	0.1791	0.037*
H1B	0.6351	0.4904	0.1597	0.037*
C2	0.7259 (2)	0.4740 (2)	0.07225 (7)	0.0251 (5)
C3	0.8761 (2)	0.3236 (2)	0.01767 (8)	0.0260 (5)
C4	0.9003 (2)	0.2913 (2)	−0.03448 (8)	0.0270 (5)
C5	0.9858 (2)	0.1962 (2)	−0.05694 (8)	0.0316 (5)
H5	1.0486	0.1313	−0.0415	0.038*
C6	0.9623 (2)	0.2131 (2)	−0.10836 (8)	0.0336 (6)
H6	1.0069	0.1616	−0.1341	0.04*
C7	0.8651 (2)	0.3157 (2)	−0.11361 (8)	0.0330 (6)
H7	0.8296	0.3482	−0.1444	0.04*
C8	0.8284 (2)	0.5288 (2)	0.19216 (8)	0.0272 (5)
C9	0.9223 (2)	0.6243 (2)	0.17099 (9)	0.0320 (5)
H9	0.9287	0.6313	0.1361	0.038*
C10	1.0065 (3)	0.7093 (3)	0.20046 (10)	0.0389 (6)
H10	1.0706	0.7739	0.1855	0.047*
C11	0.9987 (3)	0.7014 (3)	0.25126 (10)	0.0388 (6)
H11	1.0563	0.7606	0.2713	0.047*
C12	0.9063 (3)	0.6063 (3)	0.27252 (9)	0.0388 (6)
H12	0.9001	0.6	0.3074	0.047*
C13	0.8222 (2)	0.5198 (3)	0.24330 (8)	0.0333 (6)
H13	0.7598	0.4539	0.2584	0.04*
O1	0.94160 (17)	0.26029 (17)	0.04999 (6)	0.0314 (4)
O2	0.82422 (16)	0.36671 (15)	−0.06877 (5)	0.0309 (4)
N1	0.7763 (2)	0.41033 (19)	0.11201 (6)	0.0275 (4)
H1	0.8432	0.3465	0.1081	0.033*
N2	0.77589 (19)	0.42680 (19)	0.02701 (6)	0.0262 (4)
H2	0.739	0.4679	0.0009	0.031*
S1	0.60657 (6)	0.60581 (6)	0.072955 (19)	0.03259 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (12)	0.0375 (13)	0.0220 (11)	−0.0027 (11)	0.0039 (9)	0.0008 (10)
C2	0.0253 (11)	0.0269 (11)	0.0231 (11)	−0.0052 (9)	0.0015 (9)	−0.0028 (9)
C3	0.0227 (11)	0.0265 (11)	0.0289 (12)	−0.0054 (10)	0.0013 (9)	−0.0005 (9)
C4	0.0289 (12)	0.0274 (12)	0.0248 (11)	−0.0019 (10)	−0.0021 (9)	0.0017 (9)
C5	0.0310 (13)	0.0319 (12)	0.0318 (12)	0.0041 (10)	0.0005 (10)	−0.0019 (10)
C6	0.0396 (14)	0.0353 (13)	0.0260 (12)	0.0033 (11)	0.0041 (10)	−0.0041 (10)
C7	0.0411 (14)	0.0380 (13)	0.0200 (11)	0.0024 (11)	0.0016 (10)	−0.0032 (10)
C8	0.0304 (12)	0.0266 (12)	0.0246 (11)	0.0077 (10)	0.0000 (9)	−0.0018 (9)
C9	0.0354 (13)	0.0324 (12)	0.0283 (12)	0.0043 (11)	0.0009 (10)	0.0006 (11)
C10	0.0381 (14)	0.0358 (13)	0.0427 (15)	−0.0012 (12)	−0.0005 (11)	−0.0003 (11)
C11	0.0399 (14)	0.0381 (13)	0.0385 (14)	0.0034 (12)	−0.0058 (12)	−0.0074 (12)
C12	0.0451 (15)	0.0452 (15)	0.0261 (12)	0.0097 (13)	−0.0045 (11)	−0.0035 (11)
C13	0.0376 (13)	0.0347 (13)	0.0277 (13)	0.0048 (11)	0.0023 (11)	0.0020 (10)
O1	0.0327 (9)	0.0354 (9)	0.0262 (8)	0.0035 (7)	−0.0005 (7)	0.0009 (7)
O2	0.0354 (9)	0.0319 (9)	0.0253 (8)	0.0060 (7)	−0.0011 (7)	−0.0017 (7)
N1	0.0303 (10)	0.0287 (10)	0.0236 (9)	0.0027 (8)	0.0016 (8)	−0.0010 (8)
N2	0.0288 (10)	0.0291 (10)	0.0208 (9)	0.0010 (8)	−0.0008 (8)	−0.0012 (8)
S1	0.0371 (3)	0.0324 (3)	0.0283 (3)	0.0066 (3)	0.0013 (3)	−0.0021 (2)

C1—N1	1.456 (3)	C7—O2	1.363 (2)
C1—C8	1.515 (3)	C7—H7	0.95
C1—H1A	0.99	C8—C9	1.389 (3)
C1—H1B	0.99	C8—C13	1.390 (3)
C2—N1	1.323 (3)	C9—C10	1.384 (3)
C2—N2	1.388 (3)	C9—H9	0.95
C2—S1	1.679 (2)	C10—C11	1.381 (4)
C3—O1	1.228 (3)	C10—H10	0.95
C3—N2	1.382 (3)	C11—C12	1.379 (4)
C3—C4	1.464 (3)	C11—H11	0.95
C4—C5	1.353 (3)	C12—C13	1.387 (4)
C4—O2	1.374 (2)	C12—H12	0.95
C5—C6	1.420 (3)	C13—H13	0.95
C5—H5	0.95	N1—H1	0.88
C6—C7	1.342 (3)	N2—H2	0.88
C6—H6	0.95
N1—C1—C8	114.11 (18)	C9—C8—C1	122.5 (2)
N1—C1—H1A	108.7	C13—C8—C1	118.8 (2)
C8—C1—H1A	108.7	C10—C9—C8	120.3 (2)
N1—C1—H1B	108.7	C10—C9—H9	119.8
C8—C1—H1B	108.7	C8—C9—H9	119.8
H1A—C1—H1B	107.6	C11—C10—C9	120.9 (2)
N1—C2—N2	116.84 (18)	C11—C10—H10	119.6
N1—C2—S1	124.70 (16)	C9—C10—H10	119.6
N2—C2—S1	118.46 (15)	C12—C11—C10	119.1 (2)
O1—C3—N2	123.90 (19)	C12—C11—H11	120.5
O1—C3—C4	120.59 (19)	C10—C11—H11	120.5
N2—C3—C4	115.51 (18)	C11—C12—C13	120.5 (2)
C5—C4—O2	110.61 (18)	C11—C12—H12	119.8
C5—C4—C3	131.8 (2)	C13—C12—H12	119.8
O2—C4—C3	117.63 (18)	C12—C13—C8	120.6 (2)
C4—C5—C6	105.9 (2)	C12—C13—H13	119.7
C4—C5—H5	127.1	C8—C13—H13	119.7
C6—C5—H5	127.1	C7—O2—C4	105.78 (17)
C7—C6—C5	107.0 (2)	C2—N1—C1	123.51 (18)
C7—C6—H6	126.5	C2—N1—H1	118.2
C5—C6—H6	126.5	C1—N1—H1	118.2
C6—C7—O2	110.8 (2)	C3—N2—C2	128.43 (18)
C6—C7—H7	124.6	C3—N2—H2	115.8
O2—C7—H7	124.6	C2—N2—H2	115.8
C9—C8—C13	118.6 (2)
O1—C3—C4—C5	1.4 (4)	C10—C11—C12—C13	0.0 (4)
N2—C3—C4—C5	−178.1 (2)	C11—C12—C13—C8	−0.8 (3)
O1—C3—C4—O2	−179.53 (19)	C9—C8—C13—C12	1.1 (3)
N2—C3—C4—O2	1.0 (3)	C1—C8—C13—C12	−175.5 (2)
O2—C4—C5—C6	0.2 (3)	C6—C7—O2—C4	−0.1 (2)
C3—C4—C5—C6	179.3 (2)	C5—C4—O2—C7	−0.1 (2)
C4—C5—C6—C7	−0.2 (3)	C3—C4—O2—C7	−179.4 (2)
C5—C6—C7—O2	0.2 (3)	N2—C2—N1—C1	−175.32 (19)
N1—C1—C8—C9	27.7 (3)	S1—C2—N1—C1	4.4 (3)
N1—C1—C8—C13	−155.8 (2)	C8—C1—N1—C2	−104.7 (2)
C13—C8—C9—C10	−0.6 (3)	O1—C3—N2—C2	−3.1 (3)
C1—C8—C9—C10	175.9 (2)	C4—C3—N2—C2	176.4 (2)
C8—C9—C10—C11	−0.3 (4)	N1—C2—N2—C3	−2.3 (3)
C9—C10—C11—C12	0.6 (4)	S1—C2—N2—C3	178.05 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	2.00	2.697 (3)	135
N2—H2···S1i	0.88	2.70	3.578 (2)	174
C7—H7···O1ii	0.95	2.58	3.423 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.88	2.00	2.697 (3)	135
N2—H2⋯S1i	0.88	2.70	3.578 (2)	174
C7—H7⋯O1ii	0.95	2.58	3.423 (3)	148

Symmetry codes: (i) ; (ii) .