N-(2-Chloro­benzo­yl)-N′-(3-pyrid­yl)thio­urea

Chai, L.-Q.; Ding, Y.-J.; Yang, X.-Q.; Yan, H.-B.; Dong, W.-K.

doi:10.1107/S1600536808019922

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1407

doi:10.1107/S1600536808019922

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N-(2-Chlorobenzoyl)-N′-(3-pyridyl)thiourea

Lan-Qin Chai,^a Yu-Jie Ding,^b Xiao-Qing Yang,^a Hai-Bo Yan ^a and Wen-Kui Dong ^a ^*

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

(Received 14 June 2008; accepted 30 June 2008; online 5 July 2008)

In the molecule of the title compound, C₁₃H₁₀ClN₃OS, the dihedral angles between the plane through the thiourea group and the pyridine and benzene rings are 53.08 (3) and 87.12 (3)°, respectively. The molecules are linked by intermolecular N—H⋯N hydrogen-bonding interactions to form a supramolecular chain structure along the a axis. An intramolecular N—H⋯O hydrogen bond is also present.

Related literature

For related literature, see: Campo et al. (2002 ); Dong et al. (2006 , 2008 ); Foss et al. (2004 ); Guillon et al. (1996 ); Koch (2001 ); Krepps et al. (2001 ); Su et al. (2004 , 2006 ); Teoh et al. (1999 ); Venkatachalam et al. (2004 ); West et al. (2000 ); Xian et al. (2004 ).

Experimental

Crystal data

C₁₃H₁₀ClN₃OS
M_r = 291.75
Triclinic, $[P \overline 1]$
a = 8.421 (3) Å
b = 9.282 (4) Å
c = 10.512 (4) Å
α = 98.336 (4)°
β = 110.797 (4)°
γ = 112.532 (4)°
V = 670.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 298 (2) K
0.32 × 0.11 × 0.07 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.874, T_max = 0.972
3504 measured reflections
2319 independent reflections
1734 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
2319 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 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	1.98	2.671 (3)	137
N1—H1⋯N3ⁱ	0.86	2.08	2.886 (4)	157
Symmetry code: (i) x-1, y, z.

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/S1600536808019922/rz2227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019922/rz2227Isup2.hkl

checkCIF report

Comment top

Thiourea and its substituted derivatives have attracted much attention because of their unique properties, such as the strong coordination ability (Su et al., 2004; Su et al., 2006; Xian et al., 2004; West et al., 2000). They are used as selective analytical reagents, especially for the determination of transition metals in complex interfering matrices (Koch, 2001; Foss et al., 2004). It has been shown that the redox properties of thiourea are markedly influenced by electronic factors (Guillon et al., 1996), and the biological activity of thiourea derivatives has also been reported in the literature (Teoh et al., 1999; Campo et al., 2002). However, the study of S···H interactions may have fundamental importance in biochemical research due to the fact that living systems contain several important sulfur-containing molecules, such as the aminoacids cysteine and methionine (Krepps et al., 2001). Related to the biological relevance of S···H interactions, Uckum and coworkers have recently reported a structural study of a series of thiourea compounds (Venkatachalam et al., 2004). Here we report the synthesis and crystal structure of a new benzoylthiourea derivative, N-(o-chloro)benzoyl-N'-(3-pyridyl)thiourea. The molecular structure of the title compound is shown in Figure 1.

The dihedral angles formed by the plane through the thiourea group and the pyridine and benzene rings of 53.08 (3) and 87.12 (3)°, respectively. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen bonding interaction (Table 1), forming a planar six-membered ring. In contrast to other thiourea compounds, the H1···S1 separation is 2.662 (2) Å, indicating that S1 is not involved in hydrogen bonding. This situation is similar to that found in the structure of N-benzoyl-N'-(3-pyridyl)thiourea (Dong et al., 2006). The C=O bond length of 1.217 (3) Å is just significantly longer than the average C=O bond length (1.200 Å) due to the intramolecular hydrogen bond. In the crystal structure, molecules are linked by intermolecular by N—H···N hydrogen interactions to form supramolecular chains along the a axis.

Related literature top

For related literature, see: Campo et al. (2002); Dong et al. (2006, 2008); Foss et al. (2004); Guillon et al. (1996); Koch (2001); Krepps et al. (2001); Su et al. (2004, 2006); Teoh et al. (1999); Venkatachalam et al. (2004); West et al. (2000); Xian et al. (2004).

Experimental top

N-(o-Chloro)benzoyl-N'-(3-pyridyl)thiourea was synthesized according the method reported in the literature (Dong et al., 2008). o-Chlorobenzoyl chloride (3.61 g, 0.02 mol) was reacted with ammonium thiocyanate (2.28 g, 0.03 mol) in CH₂Cl₂ (25 ml) under solid-liquid phase transfer catalysis, using 3% polyethylene glycol-400 (0.36 g) as catalyst, to give the corresponding benzoyl isothiocyanate, which was reacted with 3-aminopyridine (1.72 g, 0.02 mol). The title compound precipitated immediately. The product was filtered, washed with water and CH₂Cl₂ and dried. Colourless needle-shaped single crystals were obtained by slow evaporation of an acetone solution after several weeks at room temperature. M.p. 442 - 444 K. Anal. Calcd. for C₁₃H₁₀ClN₃OS: C, 53.52; H, 3.45; N, 14.40. Found: C, 53.28; H, 3.48; N, 14.15%.

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 molecule structure of the title compound with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. The supramolecular chain structure of the title compound constructed by intermolecular N—H···N hydrogen bonding interactions (dotted lines).

N-(2-Chlorobenzoyl)-N'-(3-pyridyl)thiourea top

Crystal data top

C₁₃H₁₀ClN₃OS	Z = 2
M_r = 291.75	F(000) = 300
Triclinic, P1	D_x = 1.444 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.421 (3) Å	Cell parameters from 1514 reflections
b = 9.282 (4) Å	θ = 2.5–26.6°
c = 10.512 (4) Å	µ = 0.43 mm⁻¹
α = 98.336 (4)°	T = 298 K
β = 110.797 (4)°	Needle, colourless
γ = 112.532 (4)°	0.32 × 0.11 × 0.07 mm
V = 670.9 (5) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2319 independent reflections
Radiation source: fine-focus sealed tube	1734 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.874, T_max = 0.972	k = −11→9
3504 measured reflections	l = −12→9

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.044P)² + 0.2146P] where P = (F_o² + 2F_c²)/3
2319 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₃H₁₀ClN₃OS	γ = 112.532 (4)°
M_r = 291.75	V = 670.9 (5) Å³
Triclinic, P1	Z = 2
a = 8.421 (3) Å	Mo Kα radiation
b = 9.282 (4) Å	µ = 0.43 mm⁻¹
c = 10.512 (4) Å	T = 298 K
α = 98.336 (4)°	0.32 × 0.11 × 0.07 mm
β = 110.797 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2319 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1734 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.972	R_int = 0.019
3504 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2319 reflections	Δρ_min = −0.18 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
Cl1	0.41414 (14)	0.64074 (11)	0.50918 (8)	0.0781 (3)
N1	0.4306 (3)	0.5361 (2)	0.1841 (2)	0.0397 (5)
H1	0.3077	0.4966	0.1477	0.048*
N2	0.6871 (3)	0.4903 (2)	0.2029 (2)	0.0416 (5)
H2	0.7561	0.5927	0.2548	0.050*
N3	1.0366 (3)	0.3871 (2)	0.1394 (2)	0.0481 (5)
O1	0.7112 (3)	0.7734 (2)	0.3311 (2)	0.0630 (5)
S1	0.33789 (9)	0.24252 (8)	0.02568 (7)	0.0500 (2)
C1	0.4967 (3)	0.4294 (3)	0.1432 (2)	0.0370 (5)
C2	0.5364 (4)	0.6956 (3)	0.2748 (3)	0.0422 (6)
C3	0.4139 (3)	0.7708 (3)	0.2962 (2)	0.0400 (5)
C4	0.3540 (4)	0.7557 (3)	0.4027 (3)	0.0476 (6)
C5	0.2449 (4)	0.8281 (3)	0.4233 (3)	0.0560 (7)
H5	0.2062	0.8177	0.4955	0.067*
C6	0.1944 (4)	0.9154 (3)	0.3359 (3)	0.0613 (8)
H6	0.1211	0.9644	0.3490	0.074*
C7	0.2513 (4)	0.9307 (3)	0.2296 (3)	0.0593 (7)
H7	0.2157	0.9895	0.1705	0.071*
C8	0.3611 (4)	0.8595 (3)	0.2093 (3)	0.0495 (6)
H8	0.3997	0.8711	0.1371	0.059*
C9	0.9299 (3)	0.4610 (3)	0.1477 (2)	0.0411 (6)
H9	0.9551	0.5586	0.1259	0.049*
C10	0.7848 (3)	0.3985 (3)	0.1872 (2)	0.0380 (5)
C11	0.7442 (4)	0.2524 (3)	0.2178 (3)	0.0481 (6)
H11	0.6456	0.2070	0.2436	0.058*
C12	0.8523 (4)	0.1757 (3)	0.2093 (3)	0.0542 (7)
H12	0.8291	0.0776	0.2300	0.065*
C13	0.9953 (4)	0.2463 (3)	0.1697 (3)	0.0537 (7)
H13	1.0674	0.1930	0.1636	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1271 (8)	0.0975 (6)	0.0704 (5)	0.0861 (6)	0.0617 (5)	0.0496 (5)
N1	0.0341 (10)	0.0395 (11)	0.0488 (11)	0.0192 (9)	0.0225 (9)	0.0076 (9)
N2	0.0372 (11)	0.0368 (10)	0.0569 (12)	0.0195 (9)	0.0271 (10)	0.0101 (9)
N3	0.0439 (12)	0.0496 (12)	0.0650 (14)	0.0268 (10)	0.0339 (11)	0.0184 (11)
O1	0.0406 (11)	0.0539 (11)	0.0758 (13)	0.0192 (9)	0.0209 (10)	−0.0069 (10)
S1	0.0487 (4)	0.0416 (4)	0.0571 (4)	0.0206 (3)	0.0259 (3)	0.0051 (3)
C1	0.0437 (14)	0.0408 (13)	0.0405 (13)	0.0244 (11)	0.0273 (11)	0.0160 (10)
C2	0.0426 (15)	0.0419 (13)	0.0447 (14)	0.0219 (12)	0.0227 (12)	0.0074 (11)
C3	0.0408 (13)	0.0356 (12)	0.0459 (14)	0.0206 (11)	0.0213 (11)	0.0071 (11)
C4	0.0624 (17)	0.0491 (14)	0.0487 (14)	0.0376 (13)	0.0297 (13)	0.0177 (12)
C5	0.0712 (19)	0.0653 (17)	0.0544 (16)	0.0448 (16)	0.0386 (15)	0.0170 (14)
C6	0.0686 (19)	0.0596 (17)	0.0696 (19)	0.0464 (16)	0.0307 (16)	0.0129 (15)
C7	0.0712 (19)	0.0516 (16)	0.0672 (18)	0.0404 (15)	0.0291 (16)	0.0236 (14)
C8	0.0577 (16)	0.0438 (14)	0.0540 (15)	0.0264 (13)	0.0293 (13)	0.0168 (12)
C9	0.0374 (13)	0.0396 (13)	0.0515 (14)	0.0198 (11)	0.0238 (12)	0.0142 (11)
C10	0.0388 (13)	0.0410 (13)	0.0432 (13)	0.0231 (11)	0.0236 (11)	0.0120 (10)
C11	0.0507 (15)	0.0512 (15)	0.0599 (16)	0.0269 (13)	0.0380 (13)	0.0222 (13)
C12	0.0630 (17)	0.0487 (15)	0.0750 (18)	0.0351 (14)	0.0422 (15)	0.0300 (14)
C13	0.0556 (16)	0.0537 (16)	0.0732 (18)	0.0373 (14)	0.0378 (15)	0.0220 (14)

Geometric parameters (Å, º) top

Cl1—C4	1.734 (2)	C5—C6	1.372 (4)
N1—C2	1.368 (3)	C5—H5	0.9300
N1—C1	1.394 (3)	C6—C7	1.369 (4)
N1—H1	0.8600	C6—H6	0.9300
N2—C1	1.331 (3)	C7—C8	1.380 (4)
N2—C10	1.422 (3)	C7—H7	0.9300
N2—H2	0.8600	C8—H8	0.9300
N3—C13	1.335 (3)	C9—C10	1.375 (3)
N3—C9	1.340 (3)	C9—H9	0.9300
O1—C2	1.217 (3)	C10—C11	1.381 (3)
S1—C1	1.659 (2)	C11—C12	1.371 (3)
C2—C3	1.508 (3)	C11—H11	0.9300
C3—C4	1.385 (3)	C12—C13	1.373 (3)
C3—C8	1.386 (3)	C12—H12	0.9300
C4—C5	1.384 (3)	C13—H13	0.9300

C2—N1—C1	128.3 (2)	C7—C6—H6	119.8
C2—N1—H1	115.9	C5—C6—H6	119.8
C1—N1—H1	115.9	C6—C7—C8	120.5 (2)
C1—N2—C10	124.83 (19)	C6—C7—H7	119.7
C1—N2—H2	117.6	C8—C7—H7	119.7
C10—N2—H2	117.6	C7—C8—C3	120.1 (2)
C13—N3—C9	117.2 (2)	C7—C8—H8	119.9
N2—C1—N1	115.4 (2)	C3—C8—H8	119.9
N2—C1—S1	125.54 (17)	N3—C9—C10	122.6 (2)
N1—C1—S1	119.02 (17)	N3—C9—H9	118.7
O1—C2—N1	124.8 (2)	C10—C9—H9	118.7
O1—C2—C3	122.1 (2)	C9—C10—C11	119.2 (2)
N1—C2—C3	113.1 (2)	C9—C10—N2	119.10 (19)
C4—C3—C8	118.6 (2)	C11—C10—N2	121.6 (2)
C4—C3—C2	121.6 (2)	C12—C11—C10	118.6 (2)
C8—C3—C2	119.8 (2)	C12—C11—H11	120.7
C5—C4—C3	121.1 (2)	C10—C11—H11	120.7
C5—C4—Cl1	119.9 (2)	C11—C12—C13	118.8 (2)
C3—C4—Cl1	118.97 (18)	C11—C12—H12	120.6
C6—C5—C4	119.2 (2)	C13—C12—H12	120.6
C6—C5—H5	120.4	N3—C13—C12	123.6 (2)
C4—C5—H5	120.4	N3—C13—H13	118.2
C7—C6—C5	120.4 (2)	C12—C13—H13	118.2

C10—N2—C1—N1	173.77 (19)	C4—C5—C6—C7	0.0 (4)
C10—N2—C1—S1	−7.1 (3)	C5—C6—C7—C8	−0.4 (4)
C2—N1—C1—N2	1.6 (3)	C6—C7—C8—C3	0.4 (4)
C2—N1—C1—S1	−177.58 (18)	C4—C3—C8—C7	0.0 (4)
C1—N1—C2—O1	3.2 (4)	C2—C3—C8—C7	−179.1 (2)
C1—N1—C2—C3	−178.6 (2)	C13—N3—C9—C10	0.8 (4)
O1—C2—C3—C4	−93.6 (3)	N3—C9—C10—C11	−1.0 (4)
N1—C2—C3—C4	88.1 (3)	N3—C9—C10—N2	175.7 (2)
O1—C2—C3—C8	85.4 (3)	C1—N2—C10—C9	129.9 (2)
N1—C2—C3—C8	−92.8 (3)	C1—N2—C10—C11	−53.4 (3)
C8—C3—C4—C5	−0.4 (4)	C9—C10—C11—C12	0.8 (4)
C2—C3—C4—C5	178.7 (2)	N2—C10—C11—C12	−175.8 (2)
C8—C3—C4—Cl1	178.40 (18)	C10—C11—C12—C13	−0.5 (4)
C2—C3—C4—Cl1	−2.5 (3)	C9—N3—C13—C12	−0.5 (4)
C3—C4—C5—C6	0.4 (4)	C11—C12—C13—N3	0.4 (4)
Cl1—C4—C5—C6	−178.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.98	2.671 (3)	137
N1—H1···N3ⁱ	0.86	2.08	2.886 (4)	157

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClN₃OS
M_r	291.75
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.421 (3), 9.282 (4), 10.512 (4)
α, β, γ (°)	98.336 (4), 110.797 (4), 112.532 (4)
V (Å³)	670.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.32 × 0.11 × 0.07

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.874, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	3504, 2319, 1734
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.02
No. of reflections	2319
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

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	1.98	2.671 (3)	136.8
N1—H1···N3ⁱ	0.86	2.08	2.886 (4)	156.9

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604-01) and the 'Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03-01 A), which are gratefully acknowledged.

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