N-(2-Furo-yl)-N'-(2-pyrid-yl)thio-urea.

The title compound, C(11)H(9)N(3)O(2)S, crystallizes with two independent mol-ecules in the asymmetric unit. The central thio-urea core makes dihedral angles of -3.3 (3) and 0.6 (3)° with the furan carbonyl groups in each mol-ecule, whereas the pyridine ring is inclined by 4.63 (2) and 11.28 (7)°, respectively. The trans-cis geometry of the thio-urea fragment is stabilized by an intra-molecular N-H⋯N hydrogen bond between the H atom of the cis-thio-amide group and the pyridine N atom. In the crystal structure, inter-molecular bifurcated N-H⋯S and N-H⋯O hydrogen bonds form centrosymmetric tetra-mers extending along the b axis.

Related literature

For general background, see: Aly et al. (2007 ▶); Su et al. (2006 ▶). For related structures, see: Duque et al. (2008 ▶); Corrêa et al. (2008 ▶); Theodoro et al. (2008 ▶); Valdés-Martínez et al. (2002 ▶); Koch (2001 ▶); Pérez et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).

Experimental

Crystal data

C11H9N3n class="Chemical">O2S

M = 247.27

Monoclinic,

a = 6.9510 (1) Å

b = 15.7000 (4) Å

c = 20.2700 (6) Å

β = 90.284 (2)°

V = 2212.05 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.12 × 0.08 × 0.06 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

Absorption correction: none

22281 measured reflections

4337 independent reflections

3574 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.10

4337 reflections

323 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.46 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011301/ng2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011301/ng2563Isup2.hkl

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

C11H9N3O2S	F(000) = 1024
Mr = 247.27	Dx = 1.485 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13181 reflections
a = 6.9510 (1) Å	θ = 2.9–26.0°
b = 15.7000 (4) Å	µ = 0.28 mm−1
c = 20.2700 (6) Å	T = 150 K
β = 90.284 (2)°	Block, colorless
V = 2212.05 (9) Å3	0.12 × 0.08 × 0.06 mm
Z = 8

Enraf–Nonius KappaCCD diffractometer	3574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Enraf Nonius FR590	Rint = 0.060
horizontally mounted graphite crystal	θmax = 26.0°, θmin = 2.9°
φ scans and ω scans with κ offsets	h = −8→8
22281 measured reflections	k = −19→18
4337 independent reflections	l = −24→24

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.3338P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.45 e Å−3
4337 reflections	Δρmin = −0.46 e Å−3
323 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
S1A	0.26900 (7)	0.58701 (3)	−0.01361 (2)	0.03185 (16)
S1	0.86024 (7)	0.20621 (3)	−0.13099 (2)	0.03742 (17)
N1A	0.0427 (2)	0.55696 (11)	0.09207 (8)	0.0285 (4)
O1A	−0.12681 (18)	0.64878 (9)	0.02319 (7)	0.0327 (3)
O2	0.7008 (2)	−0.07818 (9)	0.00044 (7)	0.0379 (4)
N3	0.8621 (2)	0.08935 (10)	0.07607 (8)	0.0313 (4)
N2A	0.3235 (2)	0.48042 (10)	0.08445 (8)	0.0292 (4)
N1	0.7790 (2)	0.07419 (10)	−0.04921 (9)	0.0297 (4)
O2A	−0.23343 (19)	0.56744 (9)	0.18216 (7)	0.0370 (3)
N2	0.8903 (2)	0.19839 (11)	−0.00248 (8)	0.0278 (4)
C3	0.6597 (3)	−0.06607 (12)	−0.06512 (10)	0.0311 (4)
C2A	0.2051 (2)	0.53986 (12)	0.05684 (9)	0.0268 (4)
C1	0.6980 (3)	0.01830 (13)	−0.09411 (10)	0.0330 (4)
C11	0.8702 (3)	0.06331 (14)	0.13915 (10)	0.0370 (5)
H11	0.8452	0.0063	0.1483	0.044*
N3A	0.1495 (2)	0.44154 (11)	0.17897 (8)	0.0316 (4)
C1A	−0.1108 (3)	0.60931 (12)	0.07437 (9)	0.0277 (4)
C11A	0.1415 (3)	0.40025 (13)	0.23715 (10)	0.0358 (5)
H11A	0.0287	0.4035	0.2615	0.043*
C7A	0.3113 (3)	0.43617 (12)	0.14412 (10)	0.0294 (4)
C7	0.8961 (2)	0.17098 (12)	0.06335 (9)	0.0270 (4)
O1	0.6582 (3)	0.03377 (10)	−0.15091 (8)	0.0527 (4)
C8	0.9405 (3)	0.23029 (14)	0.11254 (10)	0.0340 (4)
H8	0.9641	0.2871	0.1022	0.041*
C3A	−0.2598 (3)	0.61301 (12)	0.12527 (9)	0.0290 (4)
C6A	−0.3910 (3)	0.58333 (14)	0.22036 (11)	0.0404 (5)
H6A	−0.4116	0.5604	0.262	0.048*
C10A	0.2925 (3)	0.35352 (14)	0.26215 (11)	0.0411 (5)
H10A	0.2823	0.3257	0.3025	0.049*
C4A	−0.4268 (3)	0.65642 (12)	0.12727 (10)	0.0312 (4)
H4A	−0.4767	0.6921	0.0948	0.037*
C6	0.6596 (3)	−0.16117 (14)	0.01396 (12)	0.0418 (5)
H6	0.6744	−0.1867	0.0551	0.05*
C9	0.9482 (3)	0.20191 (14)	0.17660 (11)	0.0401 (5)
H9	0.9766	0.2398	0.2105	0.048*
C2	0.8401 (2)	0.15650 (12)	−0.05889 (9)	0.0275 (4)
C5A	−0.5112 (3)	0.63660 (14)	0.18931 (11)	0.0368 (5)
H5A	−0.6279	0.6569	0.2052	0.044*
C10	0.9135 (3)	0.11655 (15)	0.19077 (10)	0.0389 (5)
H10	0.9195	0.0963	0.2338	0.047*
C9A	0.4598 (3)	0.34887 (15)	0.22583 (11)	0.0448 (5)
H9A	0.5645	0.3182	0.2418	0.054*
C4	0.5942 (3)	−0.13956 (14)	−0.09150 (12)	0.0410 (5)
H4	0.5561	−0.1485	−0.135	0.049*
C8A	0.4710 (3)	0.38987 (14)	0.16572 (10)	0.0379 (5)
H8A	0.5818	0.3867	0.1403	0.045*
C5	0.5951 (3)	−0.20049 (14)	−0.03991 (12)	0.0410 (5)
H5	0.5577	−0.2572	−0.0431	0.049*
H2A	0.425 (3)	0.4683 (14)	0.0623 (11)	0.037 (6)*
H2	0.934 (3)	0.2477 (17)	−0.0082 (12)	0.044 (7)*
H1A	0.024 (3)	0.5257 (16)	0.1268 (12)	0.043 (6)*
H1	0.796 (3)	0.0567 (15)	−0.0081 (12)	0.041 (6)*

	U11	U22	U33	U12	U13	U23
S1A	0.0344 (3)	0.0315 (3)	0.0297 (3)	0.00331 (19)	0.00427 (19)	0.0052 (2)
S1	0.0482 (3)	0.0361 (3)	0.0280 (3)	−0.0017 (2)	0.0017 (2)	0.0040 (2)
N1A	0.0284 (8)	0.0290 (9)	0.0281 (9)	0.0000 (6)	0.0010 (6)	0.0050 (7)
O1A	0.0311 (7)	0.0331 (7)	0.0338 (8)	−0.0008 (6)	−0.0009 (5)	0.0078 (6)
O2	0.0430 (8)	0.0330 (8)	0.0377 (9)	−0.0026 (6)	0.0002 (6)	0.0033 (6)
N3	0.0331 (8)	0.0301 (9)	0.0308 (9)	−0.0014 (7)	−0.0010 (6)	0.0036 (7)
N2A	0.0291 (8)	0.0297 (9)	0.0287 (9)	0.0039 (7)	0.0026 (6)	0.0016 (7)
N1	0.0338 (9)	0.0277 (9)	0.0277 (9)	0.0000 (6)	−0.0026 (7)	0.0006 (7)
O2A	0.0383 (8)	0.0430 (9)	0.0298 (8)	0.0064 (6)	0.0011 (6)	0.0052 (6)
N2	0.0289 (8)	0.0251 (9)	0.0294 (9)	−0.0025 (7)	0.0005 (6)	0.0012 (7)
C3	0.0282 (9)	0.0312 (10)	0.0340 (11)	0.0029 (8)	−0.0028 (7)	−0.0032 (8)
C2A	0.0285 (9)	0.0236 (10)	0.0282 (10)	−0.0023 (7)	−0.0014 (7)	−0.0019 (7)
C1	0.0354 (10)	0.0309 (11)	0.0327 (12)	0.0022 (8)	−0.0039 (8)	−0.0034 (8)
C11	0.0377 (11)	0.0383 (12)	0.0351 (12)	0.0001 (9)	−0.0003 (8)	0.0087 (9)
N3A	0.0361 (9)	0.0301 (9)	0.0285 (9)	−0.0011 (7)	0.0021 (6)	0.0014 (7)
C1A	0.0275 (9)	0.0254 (10)	0.0302 (11)	−0.0045 (7)	−0.0026 (7)	0.0012 (8)
C11A	0.0466 (12)	0.0326 (11)	0.0283 (11)	−0.0042 (9)	0.0026 (8)	0.0012 (8)
C7A	0.0359 (10)	0.0242 (9)	0.0280 (10)	−0.0011 (8)	−0.0016 (8)	0.0002 (8)
C7	0.0216 (8)	0.0302 (10)	0.0293 (10)	0.0009 (7)	0.0011 (7)	0.0023 (8)
O1	0.0830 (12)	0.0382 (9)	0.0368 (9)	−0.0051 (8)	−0.0204 (8)	−0.0002 (7)
C8	0.0349 (10)	0.0325 (11)	0.0344 (11)	−0.0032 (8)	−0.0006 (8)	−0.0009 (9)
C3A	0.0313 (10)	0.0280 (10)	0.0277 (10)	−0.0029 (8)	−0.0026 (7)	0.0016 (8)
C6A	0.0450 (12)	0.0450 (13)	0.0312 (12)	−0.0007 (9)	0.0083 (9)	−0.0009 (9)
C10A	0.0553 (13)	0.0387 (12)	0.0294 (11)	0.0014 (10)	−0.0013 (9)	0.0083 (9)
C4A	0.0301 (10)	0.0285 (10)	0.0349 (11)	−0.0014 (8)	−0.0021 (7)	0.0028 (8)
C6	0.0418 (12)	0.0326 (12)	0.0510 (14)	−0.0034 (9)	0.0031 (9)	0.0079 (10)
C9	0.0415 (11)	0.0460 (13)	0.0326 (12)	0.0006 (9)	−0.0045 (8)	−0.0061 (10)
C2	0.0238 (8)	0.0273 (10)	0.0314 (11)	0.0044 (7)	0.0018 (7)	−0.0007 (8)
C5A	0.0322 (10)	0.0382 (12)	0.0401 (12)	−0.0015 (9)	0.0065 (8)	−0.0052 (9)
C10	0.0368 (11)	0.0523 (14)	0.0276 (11)	0.0016 (9)	−0.0003 (8)	0.0046 (10)
C9A	0.0500 (13)	0.0462 (13)	0.0383 (13)	0.0116 (10)	−0.0053 (10)	0.0099 (10)
C4	0.0341 (11)	0.0399 (12)	0.0489 (14)	0.0018 (9)	−0.0076 (9)	−0.0103 (10)
C8A	0.0394 (11)	0.0395 (12)	0.0348 (12)	0.0068 (9)	0.0004 (8)	0.0040 (9)
C5	0.0323 (11)	0.0302 (11)	0.0604 (15)	−0.0014 (8)	−0.0008 (9)	0.0028 (10)

S1A—C2A	1.6705 (19)	N3A—C11A	1.347 (3)
S1—C2	1.6633 (19)	C1A—C3A	1.467 (3)
N1A—C2A	1.365 (2)	C11A—C10A	1.375 (3)
N1A—C1A	1.393 (2)	C11A—H11A	0.93
N1A—H1A	0.87 (2)	C7A—C8A	1.395 (3)
O1A—C1A	1.213 (2)	C7—C8	1.398 (3)
O2—C6	1.362 (3)	C8—C9	1.373 (3)
O2—C3	1.371 (2)	C8—H8	0.93
N3—C7	1.329 (2)	C3A—C4A	1.346 (3)
N3—C11	1.343 (3)	C6A—C5A	1.338 (3)
N2A—C2A	1.363 (2)	C6A—H6A	0.93
N2A—C7A	1.398 (3)	C10A—C9A	1.381 (3)
N2A—H2A	0.86 (2)	C10A—H10A	0.93
N1—C2	1.375 (3)	C4A—C5A	1.425 (3)
N1—C1	1.382 (2)	C4A—H4A	0.93
N1—H1	0.89 (2)	C6—C5	1.330 (3)
O2A—C6A	1.367 (3)	C6—H6	0.93
O2A—C3A	1.369 (2)	C9—C10	1.392 (3)
N2—C2	1.363 (2)	C9—H9	0.93
N2—C7	1.402 (2)	C5A—H5A	0.93
N2—H2	0.84 (3)	C10—H10	0.93
C3—C4	1.350 (3)	C9A—C8A	1.381 (3)
C3—C1	1.474 (3)	C9A—H9A	0.93
C1—O1	1.207 (2)	C4—C5	1.417 (3)
C11—C10	1.371 (3)	C4—H4	0.93
C11—H11	0.93	C8A—H8A	0.93
N3A—C7A	1.334 (2)	C5—H5	0.93
C2A—N1A—C1A	128.01 (17)	C9—C8—H8	121.1
C2A—N1A—H1A	116.0 (15)	C7—C8—H8	121.1
C1A—N1A—H1A	115.3 (15)	C4A—C3A—O2A	110.57 (17)
C6—O2—C3	106.52 (16)	C4A—C3A—C1A	130.76 (18)
C7—N3—C11	118.14 (18)	O2A—C3A—C1A	118.66 (16)
C2A—N2A—C7A	131.03 (17)	C5A—C6A—O2A	110.37 (19)
C2A—N2A—H2A	115.6 (15)	C5A—C6A—H6A	124.8
C7A—N2A—H2A	113.4 (15)	O2A—C6A—H6A	124.8
C2—N1—C1	128.90 (18)	C11A—C10A—C9A	118.3 (2)
C2—N1—H1	112.8 (15)	C11A—C10A—H10A	120.8
C1—N1—H1	118.3 (15)	C9A—C10A—H10A	120.8
C6A—O2A—C3A	106.10 (15)	C3A—C4A—C5A	105.96 (18)
C2—N2—C7	131.01 (17)	C3A—C4A—H4A	127
C2—N2—H2	114.8 (16)	C5A—C4A—H4A	127
C7—N2—H2	114.0 (16)	C5—C6—O2	110.4 (2)
C4—C3—O2	109.50 (18)	C5—C6—H6	124.8
C4—C3—C1	132.2 (2)	O2—C6—H6	124.8
O2—C3—C1	118.28 (17)	C8—C9—C10	120.1 (2)
N2A—C2A—N1A	114.79 (17)	C8—C9—H9	119.9
N2A—C2A—S1A	119.45 (14)	C10—C9—H9	119.9
N1A—C2A—S1A	125.73 (14)	N2—C2—N1	114.32 (17)
O1—C1—N1	126.22 (19)	N2—C2—S1	119.24 (15)
O1—C1—C3	121.33 (18)	N1—C2—S1	126.44 (15)
N1—C1—C3	112.44 (17)	C6A—C5A—C4A	107.00 (18)
N3—C11—C10	123.3 (2)	C6A—C5A—H5A	126.5
N3—C11—H11	118.4	C4A—C5A—H5A	126.5
C10—C11—H11	118.4	C11—C10—C9	117.83 (19)
C7A—N3A—C11A	118.13 (17)	C11—C10—H10	121.1
O1A—C1A—N1A	126.07 (17)	C9—C10—H10	121.1
O1A—C1A—C3A	121.29 (17)	C10A—C9A—C8A	119.8 (2)
N1A—C1A—C3A	112.65 (16)	C10A—C9A—H9A	120.1
N3A—C11A—C10A	123.00 (19)	C8A—C9A—H9A	120.1
N3A—C11A—H11A	118.5	C3—C4—C5	106.5 (2)
C10A—C11A—H11A	118.5	C3—C4—H4	126.7
N3A—C7A—C8A	122.58 (18)	C5—C4—H4	126.7
N3A—C7A—N2A	118.80 (17)	C9A—C8A—C7A	118.12 (19)
C8A—C7A—N2A	118.60 (17)	C9A—C8A—H8A	120.9
N3—C7—C8	122.89 (18)	C7A—C8A—H8A	120.9
N3—C7—N2	118.45 (17)	C6—C5—C4	107.01 (19)
C8—C7—N2	118.65 (17)	C6—C5—H5	126.5
C9—C8—C7	117.75 (19)	C4—C5—H5	126.5
C6—O2—C3—C4	0.1 (2)	C6A—O2A—C3A—C1A	179.28 (17)
C6—O2—C3—C1	−177.81 (17)	O1A—C1A—C3A—C4A	−0.9 (3)
C7A—N2A—C2A—N1A	−2.9 (3)	N1A—C1A—C3A—C4A	179.17 (19)
C7A—N2A—C2A—S1A	175.31 (16)	O1A—C1A—C3A—O2A	−179.68 (17)
C1A—N1A—C2A—N2A	−174.81 (17)	N1A—C1A—C3A—O2A	0.4 (2)
C1A—N1A—C2A—S1A	7.1 (3)	C3A—O2A—C6A—C5A	−0.2 (2)
C2—N1—C1—O1	−3.4 (3)	N3A—C11A—C10A—C9A	0.0 (3)
C2—N1—C1—C3	177.41 (17)	O2A—C3A—C4A—C5A	−0.3 (2)
C4—C3—C1—O1	5.4 (3)	C1A—C3A—C4A—C5A	−179.11 (19)
O2—C3—C1—O1	−177.24 (19)	C3—O2—C6—C5	−0.1 (2)
C4—C3—C1—N1	−175.4 (2)	C7—C8—C9—C10	0.4 (3)
O2—C3—C1—N1	2.0 (2)	C7—N2—C2—N1	2.3 (3)
C7—N3—C11—C10	−0.6 (3)	C7—N2—C2—S1	−176.68 (14)
C2A—N1A—C1A—O1A	0.7 (3)	C1—N1—C2—N2	171.78 (17)
C2A—N1A—C1A—C3A	−179.38 (17)	C1—N1—C2—S1	−9.3 (3)
C7A—N3A—C11A—C10A	0.4 (3)	O2A—C6A—C5A—C4A	0.0 (2)
C11A—N3A—C7A—C8A	−0.1 (3)	C3A—C4A—C5A—C6A	0.1 (2)
C11A—N3A—C7A—N2A	−178.41 (17)	N3—C11—C10—C9	0.8 (3)
C2A—N2A—C7A—N3A	9.8 (3)	C8—C9—C10—C11	−0.7 (3)
C2A—N2A—C7A—C8A	−168.59 (19)	C11A—C10A—C9A—C8A	−0.7 (4)
C11—N3—C7—C8	0.3 (3)	O2—C3—C4—C5	−0.2 (2)
C11—N3—C7—N2	179.18 (16)	C1—C3—C4—C5	177.4 (2)
C2—N2—C7—N3	5.8 (3)	C10A—C9A—C8A—C7A	0.9 (3)
C2—N2—C7—C8	−175.35 (17)	N3A—C7A—C8A—C9A	−0.5 (3)
N3—C7—C8—C9	−0.2 (3)	N2A—C7A—C8A—C9A	177.75 (19)
N2—C7—C8—C9	−179.06 (16)	O2—C6—C5—C4	0.0 (2)
C6A—O2A—C3A—C4A	0.3 (2)	C3—C4—C5—C6	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.89 (2)	2.23 (2)	2.653 (2)	109.3 (18)
N1—H1···N3	0.89 (2)	1.84 (2)	2.612 (2)	145 (2)
N1A—H1A···O2A	0.87 (2)	2.22 (2)	2.661 (2)	111.6 (18)
N1A—H1A···N3A	0.87 (2)	1.90 (2)	2.632 (2)	141 (2)
N2—H2···O1Ai	0.84 (3)	2.13 (2)	2.940 (2)	162 (2)
N2A—H2A···S1Ai	0.86 (2)	2.51 (2)	3.3530 (15)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.89 (2)	2.23 (2)	2.653 (2)	109.3 (18)
N1—H1⋯N3	0.89 (2)	1.84 (2)	2.612 (2)	145 (2)
N1A—H1A⋯O2A	0.87 (2)	2.22 (2)	2.661 (2)	111.6 (18)
N1A—H1A⋯N3A	0.87 (2)	1.90 (2)	2.632 (2)	141 (2)
N2—H2⋯O1Ai	0.84 (3)	2.13 (2)	2.940 (2)	162 (2)
N2A—H2A⋯S1Ai	0.86 (2)	2.51 (2)	3.3530 (15)	170 (2)

Symmetry code: (i) .