N-Benzoyl-N′-(2-chloro-3-pyrid­yl)thio­urea

Ding, Y.-J.; Yao, J.; Wu, J.-C.; Dong, W.-K.; Tong, J.-F.

doi:10.1107/S1600536809027081

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1903

doi:10.1107/S1600536809027081

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N-Benzoyl-N′-(2-chloro-3-pyridyl)thiourea

Yu-Jie Ding,^a Jian Yao,^b Jian-Chao Wu,^b Wen-Kui Dong ^b ^* and Jun-Feng Tong ^b

^aDepartment of Biochemical Engineering, Anhui University of Technology and Science, Wuhu 241000, People's Republic of China, and ^bSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 9 July 2009; accepted 10 July 2009; online 18 July 2009)

The title compound, C₁₃H₁₀ClN₃OS, was prepared by the reaction of 3-amino-2-chloropyridine with benzoyl isothiocyanate at room temperature. The thiourea group makes dihedral angles of 47.17 (5) and 51.88 (4)°, respectively, with the benzene and pyridyl rings, while the angle between the benzene and pyridine rings is 8.91 (3)°. Intermolecular hydrogen-bond interactions link neighbouring molecules into an infinite supramolecular structure.

Related literature

For the biological activities of benzanilide and its N-substituted derivatives, see: Teoh et al. (1999 ); Campo et al. (2002 ). For the functions of related chlorophenyl compounds, see: Saeed et al. (2008 ); Gowda et al. (2008a ,b ,c ). For an isomeric compound, see: Chai et al. (2008 ). For our previous work on thiourea and its derivatives, see: Dong et al. (2006 , 2007 , 2008a ,b ). For the synthetic procedure, see: Ding et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₀ClN₃OS
M_r = 291.73
Monoclinic, P 2₁ /c
a = 3.9443 (4) Å
b = 14.9250 (15) Å
c = 22.268 (2) Å
β = 93.889 (1)°
V = 1307.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 298 K
0.41 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.839, T_max = 0.924
6459 measured reflections
2315 independent reflections
1661 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.088
S = 1.03
2315 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.94	2.633 (2)	137
N1—H1⋯S1ⁱ	0.86	2.74	3.5982 (18)	178
C12—H12⋯O1ⁱⁱ	0.93	2.70	3.324 (3)	125
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027081/at2841sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027081/at2841Isup2.hkl

checkCIF report

Comment top

Benzanilide and its N-substituted derivatives have been considered to be a class of privileged structural compounds, which usually have excellent biological activities (Teoh et al., 1999; Campo et al., 2002). However, the literatures are full of the function of the 2-chloro-4-nitrophenyl (Saeed et al., 2008), 3,5-dichlorophenyl (Gowda et al., 2008a) and 3-chlorophenyl (Gowda et al., 2008b; Gowda et al., 2008c) and also structures of benzamide and related compounds. As an extension of our work (Dong et al., 2006; Dong et al., 2007; Dong et al., 2008a; Dong et al., 2008b) on synthesis and structural characterization of thiourea and its derivatives, here report the synthesis and structure of the title compound.

In the molecule of the title compound, N-benzoyl-N'-(2-chloro-3-pyridyl)thiourea (Fig. 1), which is isomeric compound to its observed in the structures of N-(2-chlorobenzoyl)-N'-(3-pyridyl)thiourea (Chai et al., 2008). The thiourea group makes dihedral angles of 47.17 (5)° and 51.88 (4)° with the benzene and pyridyl rings respectively, while the angle between the benzene and pyridine rings is 8.91 (3)°. The carbonyl group forms an intramolecular hydrogen bond with the N2—H2 group, which forms a six-membered ring (C2/N1/C1/N2/H2/O1) structure, the H2···O1 bond length is 1.94 Å. The C═O bond length with 1.218 (3) Å is longer than the average C═O bond length [1.200 Å], which is due to intramolecular hydrogen bonding. This is similar to the situation found in the structure of N-benzoyl-N'-(3-pyridyl)thiourea (Dong et al., 2006). The crystal structure is further stabilized by intermolecular N1—H1···S1 and C12—H12···O1 hydrogen bonds interactions (Table 1, Fig. 2), which link neighbouring molecules into an infinite supramolecular structure.

Related literature top

For the biological activities of benzanilide and its N-substituted derivatives, see: Teoh et al. (1999); Campo et al. (2002). For the functions of related chlorophenyl compounds, see: Saeed et al. (2008); Gowda et al. (2008a,b,c). For an isomeric compound, see: Chai et al. (2008). For our previous work on thiourea and its derivatives, see: Dong et al. (2006, 2007, 2008a,b). For the synthetic procedure, see: Ding et al. (2008). [Please check amended text]

Experimental top

N-Benzoyl-N'-(2-chloro-3-pyridyl)thiourea was synthesized according to an analogous method reported earlier (Ding et al., 2008). Benzoyl chloride (702.8 mg, 5.00 mmol) was reacted with ammonium thiocyanate (380.6 mg, 5.00 mmol) in acetonitrile solution (25 ml) continuring stirring for 3 h at room temperature, to give the corresponding benzoyl isothiocyanate, which was added 3-amino-2-chloropyrldine (642.8 mg, 5.00 mmol). After stirring for 20 h at room temperature, the precipitate was reduced pressure filtered, washed successively with acetonitrile and diethyl ether. The product was dried in vacuo, and obtained 599.2 mg of needle-like crystalline solid. Yield, 41.07%. m.p. 424–426 K. Colorless single crystals suitable for X-ray diffraction studies were obtained after two weeks by slow evaporation from a mixture of ethyl acetate/acetone (1:1) of N-benzoyl-N'-(2-chloro-3-pyridyl)thiourea at room temperture. Analysis calculated for C₁₃H₁₀ClN₃OS (%): C 53.52, H 3.45, N 14.40. Found: C 53.61, H 3.51, N 14.3.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title compound. Intramolecular and intermolecular hydrogen bonds of the title compound are shown as dashed lines.

N-Benzoyl-N'-(2-chloro-3-pyridyl)thiourea top

Crystal data top

C₁₃H₁₀ClN₃OS	F(000) = 600
M_r = 291.73	D_x = 1.482 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2087 reflections
a = 3.9443 (4) Å	θ = 2.3–25.0°
b = 14.9250 (15) Å	µ = 0.45 mm⁻¹
c = 22.268 (2) Å	T = 298 K
β = 93.889 (1)°	Needle-like, colourless
V = 1307.9 (2) Å³	0.41 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2315 independent reflections
Radiation source: fine-focus sealed tube	1661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
T_min = 0.839, T_max = 0.924	k = −17→14
6459 measured reflections	l = −26→24

Refinement top

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) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0355P)² + 0.2536P] where P = (F_o² + 2F_c²)/3
2315 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₀ClN₃OS	V = 1307.9 (2) Å³
M_r = 291.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.9443 (4) Å	µ = 0.45 mm⁻¹
b = 14.9250 (15) Å	T = 298 K
c = 22.268 (2) Å	0.41 × 0.20 × 0.18 mm
β = 93.889 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1661 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.924	R_int = 0.040
6459 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
2315 reflections	Δρ_min = −0.21 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.45798 (17)	0.45341 (4)	0.58736 (2)	0.0389 (2)
Cl1	0.4376 (2)	0.65386 (5)	0.77102 (3)	0.0581 (2)
N1	0.6989 (5)	0.61464 (12)	0.56704 (8)	0.0351 (5)
H1	0.6662	0.5986	0.5300	0.042*
N2	0.7371 (5)	0.57099 (12)	0.66633 (7)	0.0380 (5)
H2	0.8131	0.6244	0.6727	0.046*
N3	0.5774 (6)	0.49783 (16)	0.81887 (9)	0.0523 (6)
O1	0.8401 (6)	0.73435 (11)	0.62683 (7)	0.0629 (6)
C1	0.6406 (6)	0.54897 (14)	0.60938 (9)	0.0313 (5)
C2	0.8025 (7)	0.70230 (15)	0.57650 (10)	0.0387 (6)
C3	0.8633 (6)	0.75438 (14)	0.52169 (10)	0.0337 (6)
C4	1.0013 (6)	0.71616 (16)	0.47233 (10)	0.0374 (6)
H4	1.0520	0.6553	0.4724	0.045*
C5	1.0642 (7)	0.76769 (17)	0.42297 (11)	0.0475 (7)
H5	1.1643	0.7420	0.3905	0.057*
C6	0.9790 (7)	0.85723 (18)	0.42174 (12)	0.0541 (8)
H6	1.0176	0.8917	0.3881	0.065*
C7	0.8371 (7)	0.89566 (17)	0.47016 (12)	0.0534 (8)
H7	0.7760	0.9558	0.4688	0.064*
C8	0.7846 (7)	0.84549 (16)	0.52092 (11)	0.0459 (7)
H8	0.6974	0.8723	0.5543	0.055*
C9	0.5921 (6)	0.54468 (16)	0.76902 (10)	0.0386 (6)
C10	0.7247 (6)	0.51388 (15)	0.71689 (9)	0.0331 (6)
C11	0.8605 (7)	0.42887 (16)	0.71795 (11)	0.0415 (6)
H11	0.9587	0.4060	0.6844	0.050*
C12	0.8487 (7)	0.37809 (17)	0.76953 (11)	0.0488 (7)
H12	0.9360	0.3202	0.7713	0.059*
C13	0.7047 (8)	0.41517 (19)	0.81819 (12)	0.0547 (8)
H13	0.6955	0.3805	0.8527	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0473 (4)	0.0371 (4)	0.0322 (3)	−0.0108 (3)	0.0018 (3)	−0.0030 (3)
Cl1	0.0701 (5)	0.0542 (4)	0.0505 (4)	0.0118 (4)	0.0069 (4)	−0.0115 (3)
N1	0.0486 (13)	0.0312 (11)	0.0250 (10)	−0.0073 (10)	−0.0004 (9)	−0.0021 (8)
N2	0.0557 (14)	0.0300 (11)	0.0279 (10)	−0.0078 (10)	−0.0009 (9)	−0.0024 (8)
N3	0.0615 (17)	0.0609 (16)	0.0348 (12)	−0.0110 (13)	0.0049 (11)	0.0027 (11)
O1	0.1150 (19)	0.0399 (10)	0.0337 (10)	−0.0175 (11)	0.0031 (10)	−0.0068 (8)
C1	0.0322 (14)	0.0317 (12)	0.0301 (12)	0.0023 (11)	0.0040 (10)	−0.0022 (10)
C2	0.0478 (17)	0.0328 (14)	0.0352 (14)	−0.0048 (12)	0.0005 (12)	−0.0013 (11)
C3	0.0360 (15)	0.0304 (13)	0.0339 (13)	−0.0053 (11)	−0.0040 (11)	−0.0005 (10)
C4	0.0382 (15)	0.0346 (13)	0.0387 (14)	−0.0050 (11)	−0.0031 (12)	−0.0006 (11)
C5	0.0510 (18)	0.0526 (17)	0.0391 (14)	−0.0094 (14)	0.0046 (13)	−0.0014 (12)
C6	0.065 (2)	0.0529 (18)	0.0436 (16)	−0.0102 (15)	−0.0023 (14)	0.0158 (13)
C7	0.062 (2)	0.0355 (15)	0.0610 (19)	−0.0001 (14)	−0.0046 (16)	0.0089 (13)
C8	0.0536 (18)	0.0362 (15)	0.0479 (15)	0.0007 (13)	0.0037 (13)	−0.0032 (12)
C9	0.0424 (16)	0.0402 (14)	0.0331 (13)	−0.0059 (12)	0.0014 (11)	−0.0041 (11)
C10	0.0360 (15)	0.0332 (13)	0.0294 (12)	−0.0059 (11)	−0.0029 (10)	0.0006 (10)
C11	0.0479 (17)	0.0374 (14)	0.0386 (14)	−0.0008 (12)	−0.0017 (12)	−0.0028 (11)
C12	0.0556 (19)	0.0400 (15)	0.0492 (16)	−0.0053 (14)	−0.0078 (14)	0.0067 (13)
C13	0.067 (2)	0.0562 (18)	0.0398 (16)	−0.0159 (16)	−0.0051 (14)	0.0147 (14)

Geometric parameters (Å, º) top

S1—C1	1.657 (2)	C4—H4	0.9300
Cl1—C9	1.741 (2)	C5—C6	1.378 (3)
N1—C2	1.382 (3)	C5—H5	0.9300
N1—C1	1.390 (3)	C6—C7	1.374 (4)
N1—H1	0.8600	C6—H6	0.9300
N2—C1	1.340 (3)	C7—C8	1.383 (3)
N2—C10	1.416 (3)	C7—H7	0.9300
N2—H2	0.8600	C8—H8	0.9300
N3—C9	1.316 (3)	C9—C10	1.384 (3)
N3—C13	1.332 (3)	C10—C11	1.377 (3)
O1—C2	1.218 (3)	C11—C12	1.379 (3)
C2—C3	1.480 (3)	C11—H11	0.9300
C3—C4	1.382 (3)	C12—C13	1.373 (4)
C3—C8	1.395 (3)	C12—H12	0.9300
C4—C5	1.378 (3)	C13—H13	0.9300

C2—N1—C1	128.66 (18)	C7—C6—H6	120.0
C2—N1—H1	115.7	C5—C6—H6	120.0
C1—N1—H1	115.7	C6—C7—C8	120.5 (2)
C1—N2—C10	125.59 (19)	C6—C7—H7	119.8
C1—N2—H2	117.2	C8—C7—H7	119.8
C10—N2—H2	117.2	C7—C8—C3	119.5 (2)
C9—N3—C13	116.4 (2)	C7—C8—H8	120.3
N2—C1—N1	114.80 (19)	C3—C8—H8	120.3
N2—C1—S1	125.53 (17)	N3—C9—C10	124.9 (2)
N1—C1—S1	119.66 (15)	N3—C9—Cl1	116.11 (19)
O1—C2—N1	121.9 (2)	C10—C9—Cl1	119.02 (18)
O1—C2—C3	122.4 (2)	C11—C10—C9	117.4 (2)
N1—C2—C3	115.72 (19)	C11—C10—N2	122.3 (2)
C4—C3—C8	119.5 (2)	C9—C10—N2	120.2 (2)
C4—C3—C2	122.2 (2)	C10—C11—C12	119.0 (2)
C8—C3—C2	118.3 (2)	C10—C11—H11	120.5
C5—C4—C3	120.4 (2)	C12—C11—H11	120.5
C5—C4—H4	119.8	C13—C12—C11	118.3 (2)
C3—C4—H4	119.8	C13—C12—H12	120.8
C6—C5—C4	120.0 (2)	C11—C12—H12	120.8
C6—C5—H5	120.0	N3—C13—C12	123.9 (2)
C4—C5—H5	120.0	N3—C13—H13	118.0
C7—C6—C5	120.1 (2)	C12—C13—H13	118.0

C10—N2—C1—N1	−175.8 (2)	C4—C3—C8—C7	1.8 (4)
C10—N2—C1—S1	5.3 (3)	C2—C3—C8—C7	−179.7 (2)
C2—N1—C1—N2	−8.8 (4)	C13—N3—C9—C10	0.8 (4)
C2—N1—C1—S1	170.2 (2)	C13—N3—C9—Cl1	−178.04 (19)
C1—N1—C2—O1	−3.9 (4)	N3—C9—C10—C11	−2.1 (4)
C1—N1—C2—C3	176.3 (2)	Cl1—C9—C10—C11	176.72 (18)
O1—C2—C3—C4	144.0 (3)	N3—C9—C10—N2	−178.1 (2)
N1—C2—C3—C4	−36.2 (3)	Cl1—C9—C10—N2	0.7 (3)
O1—C2—C3—C8	−34.6 (4)	C1—N2—C10—C11	50.7 (3)
N1—C2—C3—C8	145.3 (2)	C1—N2—C10—C9	−133.5 (2)
C8—C3—C4—C5	0.7 (4)	C9—C10—C11—C12	2.0 (3)
C2—C3—C4—C5	−177.8 (2)	N2—C10—C11—C12	177.9 (2)
C3—C4—C5—C6	−2.2 (4)	C10—C11—C12—C13	−0.8 (4)
C4—C5—C6—C7	1.2 (4)	C9—N3—C13—C12	0.6 (4)
C5—C6—C7—C8	1.2 (4)	C11—C12—C13—N3	−0.6 (4)
C6—C7—C8—C3	−2.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.94	2.633 (2)	137
N1—H1···S1ⁱ	0.86	2.74	3.5982 (18)	178
C12—H12···O1ⁱⁱ	0.93	2.70	3.324 (3)	125

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClN₃OS
M_r	291.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	3.9443 (4), 14.9250 (15), 22.268 (2)
β (°)	93.889 (1)
V (Å³)	1307.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.41 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.839, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	6459, 2315, 1661
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.088, 1.03
No. of reflections	2315
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.94	2.633 (2)	136.7
N1—H1···S1ⁱ	0.86	2.74	3.5982 (18)	178.3
C12—H12···O1ⁱⁱ	0.93	2.70	3.324 (3)	125.1

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

The authors acknowledge financial support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University and the Natural Science Foundation of the Department of Education, An-Hui Province (grant No. KJ2009B110).

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