3-[(Furan-2-yl)carbon-yl]-1-(pyrimi-din-2-yl)thio-urea.

The title compound, C10H8N4O2S, was synthesized from furoyl isothio-cynate and 2-amino-pyrimidine in dry acetone. The two N-H groups are in an anti conformation with respect to each other and one N-H group is anti to the C=S group while the other is syn. The amide C=S and the C=O groups are syn to each other. The mean plane of the central thio-urea fragment forms dihedral angles of 13.50 (14) and 5.03 (11)° with the furan and pyrimidine rings, respectively. The dihedral angle between the furan and pyrimidine rings is 18.43 (10)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯N and weak C-H⋯S hydrogen bonds to form inversion dimers.

Related literature

For a general background to the biological activity of thio­urea, see: Koketsu & Ishihara (2006 ▶). For heterocyclic derivatives, n class="Chemical">metal complexes and mol­ecular electronics, see: Zeng et al. (2003 ▶); D’hooghe et al. (2005 ▶); Aly et al. (2007 ▶); Duque et al. (2009 ▶). For related structures, see: Singh et al. (2012 ▶); Koch (2001 ▶); Hassan et al. (2007 ▶); Pérez et al. (2008 ▶); Yan & Xue (2008 ▶).

Experimental

Crystal data

C10H8N4O2S

M = 248.26

Monoclinic,

a = 5.6962 (2) Å

b = 21.0530 (7) Å

c = 8.7901 (3) Å

β = 95.559 (3)°

V = 1049.17 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.74 mm−1

T = 123 K

0.40 × 0.22 × 0.11 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.421, T max = 1.000

6957 measured reflections

2028 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.04

2028 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044029/lh5548sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044029/lh5548Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044029/lh5548Isup3.cml

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

C10H8N4O2S	F(000) = 512
Mr = 248.26	Dx = 1.572 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 4415 reflections
a = 5.6962 (2) Å	θ = 4.2–72.7°
b = 21.0530 (7) Å	µ = 2.74 mm−1
c = 8.7901 (3) Å	T = 123 K
β = 95.559 (3)°	Plate, colorless
V = 1049.17 (6) Å3	0.40 × 0.22 × 0.11 mm
Z = 4

Agilent Xcalibur (Ruby, Gemini) diffractometer	2028 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 72.8°, θmin = 4.2°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −25→25
Tmin = 0.421, Tmax = 1.000	l = −10→9
6957 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.4136P] where P = (Fo2 + 2Fc2)/3
2028 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. FT IR (selected, KBr, cm-1):3424, 3207 [ν(N – H)]; 1712 [amide-I,C═O]; 1586, 1556 [ν(C═C)]; 1505[thioureido-I], 1327 [thioureido-II], 1177 [thioureido-III], 763 [thioureido-IV]. 1H NMR (300 MHz, dmso-d6): δ 14.08 (s, 1H, H-bonded N–H); 11.90 (s, 1H,free N–H); 8.80 (d,J = 7.1 Hz, 2H, pyrimidine CH); 8.05 (d, J = 7.5 Hz, 1H, furan CH); 7.50(d,J = 7.8 Hz, 1H, pyrimidine CH);7.30 (t, J1(H,H) = 6.8 Hz,J2(H,H) = 7.1 Hz, 1H, pyrimidine CH);6.76 (t, J(H,H) = 7.8 Hz, 1H, furan CH). 13C NMR (75 MHz,dmso-d6): δ 177.4, 158.5, 157.1, 155.4, 147.6, 146.4, 117.6, 117.1, 112.9.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.47026 (7)	0.555126 (18)	0.19269 (4)	0.02308 (17)
O1	−0.1466 (2)	0.71757 (6)	0.45239 (14)	0.0270 (3)
O2	0.0499 (2)	0.63600 (6)	0.26198 (14)	0.0283 (3)
N1	0.3619 (2)	0.61674 (6)	0.44577 (15)	0.0214 (3)
H1B	0.4047	0.6248	0.5403	0.026*
N2	0.7006 (2)	0.55592 (6)	0.46685 (16)	0.0201 (3)
H2B	0.7901	0.5300	0.4235	0.024*
N3	0.6446 (2)	0.60768 (6)	0.69888 (15)	0.0234 (3)
N4	0.9782 (2)	0.54126 (7)	0.67136 (15)	0.0216 (3)
C1	−0.1833 (3)	0.76232 (8)	0.5596 (2)	0.0285 (4)
H1A	−0.3194	0.7867	0.5597	0.034*
C2	0.0017 (3)	0.76645 (8)	0.6641 (2)	0.0304 (4)
H2A	0.0183	0.7937	0.7478	0.036*
C3	0.1690 (3)	0.72089 (8)	0.6224 (2)	0.0288 (4)
H3A	0.3162	0.7124	0.6737	0.035*
C4	0.0718 (3)	0.69251 (7)	0.49378 (18)	0.0214 (3)
C5	0.1539 (3)	0.64564 (7)	0.38553 (18)	0.0204 (3)
C6	0.5082 (3)	0.57705 (7)	0.37439 (17)	0.0192 (3)
C7	0.7750 (3)	0.56938 (7)	0.61922 (18)	0.0196 (3)
C8	0.7219 (3)	0.61687 (8)	0.84626 (19)	0.0257 (4)
H8A	0.6344	0.6426	0.9055	0.031*
C9	0.9258 (3)	0.58957 (8)	0.91292 (19)	0.0261 (4)
H9A	0.9775	0.5958	1.0154	0.031*
C10	1.0498 (3)	0.55213 (8)	0.81814 (19)	0.0250 (4)
H10A	1.1902	0.5336	0.8591	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.0259 (3)	0.0236 (3)	0.0195 (3)	0.00267 (13)	0.00100 (17)	−0.00364 (13)
O1	0.0233 (6)	0.0286 (6)	0.0280 (6)	0.0067 (5)	−0.0032 (5)	−0.0046 (5)
O2	0.0252 (6)	0.0347 (7)	0.0245 (6)	0.0026 (5)	−0.0006 (5)	−0.0060 (5)
N1	0.0242 (7)	0.0215 (6)	0.0182 (6)	0.0022 (5)	0.0012 (5)	−0.0023 (5)
N2	0.0232 (7)	0.0180 (6)	0.0195 (7)	0.0021 (5)	0.0041 (5)	−0.0022 (5)
N3	0.0273 (7)	0.0210 (6)	0.0218 (7)	0.0036 (5)	0.0024 (5)	−0.0017 (5)
N4	0.0224 (7)	0.0207 (6)	0.0217 (7)	0.0005 (5)	0.0026 (5)	−0.0017 (5)
C1	0.0292 (9)	0.0246 (8)	0.0315 (9)	0.0081 (6)	0.0023 (7)	−0.0038 (6)
C2	0.0315 (9)	0.0282 (9)	0.0304 (9)	0.0086 (7)	−0.0025 (7)	−0.0094 (7)
C3	0.0264 (8)	0.0286 (8)	0.0303 (9)	0.0072 (7)	−0.0030 (7)	−0.0073 (7)
C4	0.0198 (7)	0.0201 (7)	0.0240 (8)	0.0013 (6)	0.0010 (6)	0.0024 (6)
C5	0.0212 (7)	0.0194 (7)	0.0206 (7)	−0.0026 (6)	0.0023 (6)	0.0006 (6)
C6	0.0219 (7)	0.0152 (7)	0.0210 (7)	−0.0023 (5)	0.0042 (6)	0.0003 (5)
C7	0.0224 (8)	0.0163 (7)	0.0205 (8)	−0.0012 (6)	0.0037 (6)	0.0014 (6)
C8	0.0316 (9)	0.0240 (8)	0.0218 (8)	0.0038 (6)	0.0041 (6)	−0.0034 (6)
C9	0.0323 (9)	0.0253 (8)	0.0202 (8)	0.0011 (6)	0.0000 (6)	−0.0034 (6)
C10	0.0241 (8)	0.0258 (9)	0.0245 (9)	0.0022 (6)	−0.0011 (7)	0.0002 (6)

S1—C6	1.6565 (15)	N4—C7	1.340 (2)
O1—C1	1.363 (2)	C1—C2	1.332 (3)
O1—C4	1.3679 (19)	C1—H1A	0.9300
O2—C5	1.203 (2)	C2—C3	1.425 (2)
N1—C6	1.3739 (19)	C2—H2A	0.9300
N1—C5	1.390 (2)	C3—C4	1.349 (2)
N1—H1B	0.8600	C3—H3A	0.9300
N2—C6	1.373 (2)	C4—C5	1.478 (2)
N2—C7	1.394 (2)	C8—C9	1.375 (2)
N2—H2B	0.8600	C8—H8A	0.9300
N3—C7	1.339 (2)	C9—C10	1.389 (2)
N3—C8	1.341 (2)	C9—H9A	0.9300
N4—C10	1.335 (2)	C10—H10A	0.9300
C1—O1—C4	106.22 (13)	O1—C4—C5	115.00 (14)
C6—N1—C5	128.64 (13)	O2—C5—N1	126.67 (15)
C6—N1—H1B	115.7	O2—C5—C4	122.34 (15)
C5—N1—H1B	115.7	N1—C5—C4	110.98 (13)
C6—N2—C7	130.81 (13)	N2—C6—N1	114.28 (13)
C6—N2—H2B	114.6	N2—C6—S1	120.16 (11)
C7—N2—H2B	114.6	N1—C6—S1	125.56 (12)
C7—N3—C8	116.43 (14)	N3—C7—N4	126.26 (14)
C10—N4—C7	115.33 (14)	N3—C7—N2	119.48 (14)
C2—C1—O1	110.97 (15)	N4—C7—N2	114.26 (13)
C2—C1—H1A	124.5	N3—C8—C9	122.41 (15)
O1—C1—H1A	124.5	N3—C8—H8A	118.8
C1—C2—C3	106.41 (15)	C9—C8—H8A	118.8
C1—C2—H2A	126.8	C8—C9—C10	116.07 (15)
C3—C2—H2A	126.8	C8—C9—H9A	122.0
C4—C3—C2	106.46 (15)	C10—C9—H9A	122.0
C4—C3—H3A	126.8	N4—C10—C9	123.46 (15)
C2—C3—H3A	126.8	N4—C10—H10A	118.3
C3—C4—O1	109.94 (14)	C9—C10—H10A	118.3
C3—C4—C5	134.87 (15)
C4—O1—C1—C2	0.5 (2)	C7—N2—C6—S1	177.23 (12)
O1—C1—C2—C3	−0.5 (2)	C5—N1—C6—N2	−179.49 (14)
C1—C2—C3—C4	0.3 (2)	C5—N1—C6—S1	1.3 (2)
C2—C3—C4—O1	0.0 (2)	C8—N3—C7—N4	−2.3 (2)
C2—C3—C4—C5	174.44 (18)	C8—N3—C7—N2	177.72 (14)
C1—O1—C4—C3	−0.26 (18)	C10—N4—C7—N3	1.7 (2)
C1—O1—C4—C5	−175.93 (14)	C10—N4—C7—N2	−178.32 (13)
C6—N1—C5—O2	8.1 (3)	C6—N2—C7—N3	2.0 (2)
C6—N1—C5—C4	−171.00 (14)	C6—N2—C7—N4	−177.98 (14)
C3—C4—C5—O2	−165.63 (19)	C7—N3—C8—C9	1.0 (2)
O1—C4—C5—O2	8.6 (2)	N3—C8—C9—C10	0.6 (2)
C3—C4—C5—N1	13.5 (3)	C7—N4—C10—C9	0.2 (2)
O1—C4—C5—N1	−172.23 (12)	C8—C9—C10—N4	−1.3 (2)
C7—N2—C6—N1	−2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N3	0.86	1.89	2.6240 (18)	142
N2—H2B···N4i	0.86	2.21	3.0726 (19)	175
C10—H10A···S1i	0.93	2.76	3.5536 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯N3	0.86	1.89	2.6240 (18)	142
N2—H2B⋯N4i	0.86	2.21	3.0726 (19)	175
C10—H10A⋯S1i	0.93	2.76	3.5536 (17)	144

Symmetry code: (i) .