N-Benzoyl-N′,N′-dimethyl­thio­urea

Pérez, H.; Corrêa, R.S.; Plutín, A.M.; Álvarez, A.; Mascarenhas, Y.

doi:10.1107/S1600536811005137

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o647

doi:10.1107/S1600536811005137

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N-Benzoyl-N′,N′-dimethylthiourea

Hiram Pérez,^a ^* Rodrigo S. Corrêa,^b Ana María Plutín,^c Anislay Álvarez ^c and Yvonne Mascarenhas ^d

^aDepartamento de Química Inorgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, ^bDepartamento de Química, Universidade Federal de São Carlos, CEP 13565-905, São Carlos, SP, Brazil, ^cLaboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, and ^dGrupo de Cristalografia, Instituto de Fisica de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, Brazil
^*Correspondence e-mail: hperez@fq.uh.cu

(Received 17 December 2010; accepted 10 February 2011; online 16 February 2011)

In the title compound, C₁₀H₁₂N₂OS, the amide NCO group is twisted relative to the thioureido SCN₂ group, forming a dihedral angle of 55.3 (2)°. The crystal packing shows intermolecular N—H⋯S and weak C—H⋯O interactions, the former giving rise to the formation of centrosymmetric R₂²(8) dimers.

Related literature

For general background to N-acyl-N′,N′-disubstituted thiourea, see: Koch (2001 ); Sosa-Albertus & Piris (2001 ); Pérez et al. (2008a ). For related structures, see: Arslan et al. (2003 ); Bolte & Fink (2003 ); Pérez et al. (2008b ); Gomes et al. (2010 ). For details of the synthesis, see: Nagasawa & Mitsunobu (1981 ); Che et al. (1999 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₁₂N₂OS
M_r = 208.28
Monoclinic, P 2₁ /n
a = 10.8602 (9) Å
b = 5.5590 (6) Å
c = 18.6864 (10) Å
β = 102.768 (5)°
V = 1100.24 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 294 K
0.26 × 0.13 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: gaussian (Coppens et al., 1965 ) T_min = 0.943, T_max = 0.969
7078 measured reflections
2282 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.05
2282 reflections
133 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.85 (2)	2.65 (2)	3.4335 (17)	154.2 (18)
C10—H10C⋯O1ⁱⁱ	0.96	2.38	3.265 (3)	153
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Enraf–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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005137/gk2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005137/gk2336Isup2.hkl

checkCIF report

Comment top

N-Acyl-N',N'-disubstituted thiourea derivatives have been a subject of investigations due to their ability to form stable metal complexes (Koch et al., 2001). The crystal structure analysis of the title compound was undertaken as a continuation of our interest in these N',N'-disubstituted acylthiourea derivatives as intermediates towards novel heterocycles and for the systematic study of their bioactivity and complexation behavior (Pérez et al., 2008a). On the other hand, the crystal structure determination of this compound helps to confirm its most stable molecular conformation, previously predicted by theoretical methods (Sosa-Albertus & Piris, 2001) in order to explain the behavior of polydentate systems in alkylation reactions.

The main bond lengths of the title compound are within the ranges obtained for similar compounds (Pérez et al., 2008b; Arslan et al., 2003). The C–S and C–O bonds both show the expected double-bond character. However, the C–N bonds of acylthioureido fragment are intermediate between those expected for single and double C–N bonds (1.47 and 1.27 Å, respectively). These results can be explained by the existence of resonance in this part of the molecule. The conformation with respect to the thiocarbonyl and carbonyl groups is twisted, as reflected by the torsion angles O1/C1/N1/C2 and C1/N1/C2/N2 of -2.6 (3) and 57.9 (2)°. The dihedral angle between the O1/C1/N1 and S1/C2/N2 planes is 55.3 (2)°, while that between the O1/C1/N1 plane and the benzene ring is 35.8 (2)°. Compared to the diethyl analog (Bolte & Fink, 2003) and its monoclinic polymorph (Gomes, et al., 2010), the molecular confomation of the title molecule is significantly less twisted, as reflected by the corresponding torsion angles O/C/N/C [12.48 (4)°, in Bolte & Fink (2003); 7.58 (17)° in Gomes et al. (2010) and C/N/C/N (-80.79 (3)° in Bolte & Fink (2003); -71.44 (14)° in Gomes et al. (2010)]. The dihedral angle between the O/C/N and S/C/N planes is also smaller than those of the diethyl analog [(73.9 (2)° in Bolte & Fink (2003); 67.3 (1)° in Gomes et al. (2010)]. In the crystal structure (Fig. 2), an N—H···S(-x + 1,-y + 2,-z + 1) hydrogen bond links the molecules into R²₂(8) centrosymetric dimers (Bernstein et al., 1995) across the crystallographic centre of symmetry at (1/2, 0, 1/2). The molecules are also linked by weak C—H···O hydrogen bonds (Table 1).

Related literature top

For general background to N-acyl-N',N'-disubstituted thiourea, see: Koch (2001); Sosa-Albertus & Piris (2001); Pérez et al. (2008a). For related structures, see: Arslan et al. (2003); Bolte & Fink (2003); Pérez et al. (2008b); Gomes et al. (2010). For details of the synthesis, see: Nagasawa & Mitsunobu (1981); Che et al. (1999). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

N-Benzoyl-N',N'-dimethylthiourea was prepared using the standard procedure previously reported in the literature (Nagasawa & Mitsunobu, 1981) by the reaction of benzoyl chloride with KSCN in anhydrous acetone, and then condensation with dimethylamine. The synthesis of title compound was previously reported (Che et al., 1999). Recrystallization from acetone/water solution (1:1, v/v) yielded colourless crystals (1.6 g, 7.5 mmol, 75%). m.p. 448 K. Analysis calculated for C₁₀H₁₂N₂OS: C 57.67, H 5.80, N 13.45, S 15.40%. Found: C 57.88, H 5.92, N 13.60, S 15.19%.

Computing details top

Data collection: COLLECT (Enraf–Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The R²₂(8) centrosymmetric dimer lying across the centre of symmetry at (1/2,0, 1/2). Hydrogen bonds are shown as dashed lines [symmetry code (i) -x + 1, -y + 2, -z + 1].

N-Benzoyl-N',N'-dimethylthiourea top

Crystal data top

C₁₀H₁₂N₂OS	F(000) = 440
M_r = 208.28	D_x = 1.257 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1912 reflections
a = 10.8602 (9) Å	θ = 3.5–26.7°
b = 5.5590 (6) Å	µ = 0.26 mm⁻¹
c = 18.6864 (10) Å	T = 294 K
β = 102.768 (5)°	Prism, colourless
V = 1100.24 (16) Å³	0.26 × 0.13 × 0.13 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1762 reflections with I > 2σ(I)
ω scan	R_int = 0.041
Absorption correction: gaussian (Coppens et al., 1965)	θ_max = 26.7°, θ_min = 3.5°
T_min = 0.943, T_max = 0.969	h = −13→13
7078 measured reflections	k = −6→7
2282 independent reflections	l = −22→23

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0587P)² + 0.1899P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.17 e Å⁻³
2282 reflections	Δρ_min = −0.27 e Å⁻³
133 parameters

Crystal data top

C₁₀H₁₂N₂OS	V = 1100.24 (16) Å³
M_r = 208.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8602 (9) Å	µ = 0.26 mm⁻¹
b = 5.5590 (6) Å	T = 294 K
c = 18.6864 (10) Å	0.26 × 0.13 × 0.13 mm
β = 102.768 (5)°

Data collection top

Nonius KappaCCD diffractometer	2282 independent reflections
Absorption correction: gaussian (Coppens et al., 1965)	1762 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.969	R_int = 0.041
7078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.17 e Å⁻³
2282 reflections	Δρ_min = −0.27 e Å⁻³
133 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.

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

	x	y	z	U_iso*/U_eq
C1	0.55382 (16)	0.7917 (3)	0.35288 (9)	0.0475 (4)
C2	0.38501 (16)	0.6859 (3)	0.41573 (8)	0.0459 (4)
C3	0.69073 (16)	0.8469 (3)	0.36576 (9)	0.0484 (4)
C4	0.7314 (2)	1.0217 (4)	0.32357 (10)	0.0638 (5)
H4	0.6731	1.103	0.2878	0.077*
C5	0.8583 (2)	1.0756 (5)	0.33449 (13)	0.0778 (6)
H5	0.8853	1.1951	0.3067	0.093*
C6	0.9442 (2)	0.9537 (5)	0.38608 (14)	0.0822 (7)
H6	1.0296	0.9899	0.393	0.099*
C7	0.90569 (19)	0.7787 (5)	0.42771 (14)	0.0785 (6)
H7	0.965	0.6965	0.4627	0.094*
C8	0.77898 (18)	0.7235 (4)	0.41797 (11)	0.0608 (5)
H8	0.7529	0.6042	0.4463	0.073*
C9	0.3971 (3)	0.3391 (4)	0.33595 (14)	0.0806 (7)
H9A	0.4844	0.3341	0.3609	0.121*
H9B	0.3906	0.3891	0.2861	0.121*
H9C	0.3607	0.182	0.3366	0.121*
C10	0.19432 (19)	0.4648 (5)	0.36413 (12)	0.0753 (6)
H10A	0.1503	0.6153	0.3619	0.113*
H10B	0.1803	0.373	0.4051	0.113*
H10C	0.1636	0.3765	0.3196	0.113*
N1	0.51125 (13)	0.7326 (3)	0.41555 (8)	0.0485 (4)
N2	0.32963 (14)	0.5100 (3)	0.37299 (8)	0.0557 (4)
O1	0.48381 (12)	0.7991 (3)	0.29255 (6)	0.0623 (4)
S1	0.31430 (4)	0.84543 (10)	0.47135 (3)	0.0602 (2)
H1	0.5514 (19)	0.802 (4)	0.4545 (11)	0.066 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0508 (9)	0.0491 (10)	0.0440 (8)	0.0049 (7)	0.0133 (7)	−0.0020 (7)
C2	0.0449 (9)	0.0501 (10)	0.0416 (8)	−0.0028 (7)	0.0073 (6)	0.0012 (7)
C3	0.0505 (9)	0.0528 (10)	0.0452 (8)	0.0041 (7)	0.0176 (7)	−0.0013 (7)
C4	0.0672 (12)	0.0686 (13)	0.0596 (11)	0.0016 (10)	0.0228 (9)	0.0091 (9)
C5	0.0744 (14)	0.0826 (15)	0.0854 (14)	−0.0127 (12)	0.0369 (12)	0.0106 (13)
C6	0.0530 (12)	0.0933 (18)	0.1055 (17)	−0.0082 (11)	0.0288 (12)	0.0052 (15)
C7	0.0476 (11)	0.0905 (16)	0.0961 (16)	0.0084 (11)	0.0130 (11)	0.0168 (13)
C8	0.0541 (11)	0.0630 (12)	0.0669 (11)	0.0047 (9)	0.0170 (9)	0.0115 (9)
C9	0.0980 (17)	0.0543 (12)	0.0940 (16)	−0.0025 (11)	0.0312 (14)	−0.0231 (11)
C10	0.0614 (12)	0.0833 (16)	0.0749 (13)	−0.0227 (11)	0.0017 (10)	−0.0145 (11)
N1	0.0435 (8)	0.0610 (9)	0.0410 (7)	−0.0033 (6)	0.0093 (6)	−0.0038 (7)
N2	0.0561 (9)	0.0519 (9)	0.0582 (8)	−0.0062 (7)	0.0106 (7)	−0.0106 (7)
O1	0.0590 (8)	0.0824 (10)	0.0436 (7)	0.0056 (6)	0.0075 (6)	0.0021 (6)
S1	0.0504 (3)	0.0722 (4)	0.0626 (3)	−0.0118 (2)	0.0222 (2)	−0.0184 (2)

Geometric parameters (Å, º) top

C1—O1	1.2133 (19)	C6—H6	0.93
C1—N1	1.390 (2)	C7—C8	1.382 (3)
C1—C3	1.485 (2)	C7—H7	0.93
C2—N2	1.321 (2)	C8—H8	0.93
C2—N1	1.396 (2)	C9—N2	1.464 (3)
C2—S1	1.6759 (17)	C9—H9A	0.96
C3—C4	1.384 (3)	C9—H9B	0.96
C3—C8	1.388 (3)	C9—H9C	0.96
C4—C5	1.381 (3)	C10—N2	1.464 (2)
C4—H4	0.93	C10—H10A	0.96
C5—C6	1.364 (3)	C10—H10B	0.96
C5—H5	0.93	C10—H10C	0.96
C6—C7	1.368 (3)	N1—H1	0.85 (2)

O1—C1—N1	122.28 (16)	C7—C8—C3	119.70 (19)
O1—C1—C3	122.89 (15)	C7—C8—H8	120.1
N1—C1—C3	114.83 (14)	C3—C8—H8	120.1
N2—C2—N1	116.90 (15)	N2—C9—H9A	109.5
N2—C2—S1	123.85 (14)	N2—C9—H9B	109.5
N1—C2—S1	119.21 (12)	H9A—C9—H9B	109.5
C4—C3—C8	119.31 (17)	N2—C9—H9C	109.5
C4—C3—C1	119.15 (16)	H9A—C9—H9C	109.5
C8—C3—C1	121.52 (16)	H9B—C9—H9C	109.5
C5—C4—C3	120.14 (19)	N2—C10—H10A	109.5
C5—C4—H4	119.9	N2—C10—H10B	109.5
C3—C4—H4	119.9	H10A—C10—H10B	109.5
C6—C5—C4	120.0 (2)	N2—C10—H10C	109.5
C6—C5—H5	120	H10A—C10—H10C	109.5
C4—C5—H5	120	H10B—C10—H10C	109.5
C5—C6—C7	120.5 (2)	C1—N1—C2	123.76 (14)
C5—C6—H6	119.7	C1—N1—H1	114.1 (14)
C7—C6—H6	119.7	C2—N1—H1	113.5 (14)
C6—C7—C8	120.3 (2)	C2—N2—C10	120.48 (16)
C6—C7—H7	119.9	C2—N2—C9	123.91 (17)
C8—C7—H7	119.9	C10—N2—C9	115.48 (17)

O1—C1—C3—C4	34.5 (3)	C4—C3—C8—C7	0.8 (3)
N1—C1—C3—C4	−144.94 (17)	C1—C3—C8—C7	179.32 (19)
O1—C1—C3—C8	−144.04 (19)	O1—C1—N1—C2	−2.6 (3)
N1—C1—C3—C8	36.5 (2)	C3—C1—N1—C2	176.89 (15)
C8—C3—C4—C5	−1.3 (3)	N2—C2—N1—C1	57.9 (2)
C1—C3—C4—C5	−179.87 (19)	S1—C2—N1—C1	−124.37 (16)
C3—C4—C5—C6	1.1 (3)	N1—C2—N2—C10	−173.79 (17)
C4—C5—C6—C7	−0.4 (4)	S1—C2—N2—C10	8.6 (2)
C5—C6—C7—C8	−0.1 (4)	N1—C2—N2—C9	10.6 (3)
C6—C7—C8—C3	−0.1 (4)	S1—C2—N2—C9	−167.03 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.85 (2)	2.65 (2)	3.4335 (17)	154.2 (18)
C9—H9A···N1	0.96	2.43	2.778 (3)	101
C9—H9B···O1	0.96	2.49	2.902 (3)	106
C10—H10C···O1ⁱⁱ	0.96	2.38	3.265 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂OS
M_r	208.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	10.8602 (9), 5.5590 (6), 18.6864 (10)
β (°)	102.768 (5)
V (Å³)	1100.24 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.26 × 0.13 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Gaussian (Coppens et al., 1965)
T_min, T_max	0.943, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	7078, 2282, 1762
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.05
No. of reflections	2282
No. of parameters	133
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.27

Computer programs: COLLECT (Enraf–Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.85 (2)	2.65 (2)	3.4335 (17)	154.2 (18)
C10—H10C···O1ⁱⁱ	0.96	2.38	3.265 (3)	153

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

Acknowledgements

The authors thank the Grupo de Cristalografia, IFSC, USP, Brazil, for allowing the X-ray data collection. The authors acknowledge financial support from the PhD Cooperative Program - ICTP/CLAF. RSC thanks FAPESP for a fellowship.

References

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