1-Benzoyl-3-(4-n-butyl­phen­yl)thio­urea

Rauf, M.; Ebihara, M.; Badshah, A.; Imtiaz-ud-Din

doi:10.1107/S1600536811051774

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o120

doi:10.1107/S1600536811051774

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1-Benzoyl-3-(4-n-butylphenyl)thiourea

M. Khawar Rauf,^a Masahiro Ebihara,^b Amin Badshah ^a ^* and Imtiaz-ud-Din ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University Yanagido, Gifu 501-1193, Japan
^*Correspondence e-mail: aminbadshah@yahoo.com

(Received 21 November 2011; accepted 1 December 2011; online 14 December 2011)

The dihedral angle between the benzoyl and phenyl groups in the title compound, C₁₈H₂₀N₂OS, is 30.57 (4)°. The crystal packing is characterized by N—H⋯O hydrogen bonds. In the crysta, pairs of N—H⋯S hydrogen bonds link the molecules into inversion dimers

Related literature

For background to our work on the structural chemistry of N,N′-disubstituted thioures and for related structures, see: Khawer Rauf et al. (2009a ,b ). For bond-length data, see: Allen et al. (1987 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₈H₂₀N₂OS
M_r = 312.42
Triclinic, $[P \overline 1]$
a = 4.648 (3) Å
b = 13.274 (8) Å
c = 13.690 (8) Å
α = 106.765 (7)°
β = 90.013 (6)°
γ = 92.700 (8)°
V = 807.9 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 123 K
0.40 × 0.10 × 0.10 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
6380 measured reflections
3632 independent reflections
3242 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.103
S = 1.06
3632 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.33 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⋯O1	0.88	1.88	2.630 (2)	142
N2—H2⋯S1ⁱ	0.88	2.76	3.550 (2)	151
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPII (Johnson, 1976 ) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051774/hg5142sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051774/hg5142Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051774/hg5142Isup3.cml

checkCIF report

Comment top

The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thiourea (Khawar Rauf et al., 2009a, 2009b). Herein, as a continuation of these crytallographic studies, the structure of the title compound (I) is described, Fig. 1. Compared to N-benzoyl-N'-phenylthioureas [Cambridge Structural Database (Mogul Version 1.7; Allen, 2002)and (Allen et al., 1987)], the n-butyl substitution at C(6) on phenyl ring, implies no significant effect on these bond lengths. and show the molecule to exist in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The dihedral angles to the N(1) C(1)S(1) N(2) C(2)O(1) plane are 23.66 (8)° for the ring formed by C(13) to C(18) and 8.16 (9)° for the ring formed by C(3) to C(8). An intramolecular N—H···O H–bond is present (Table 1), forming a six-membered ring commonly observed in this class of compounds (Khawar Rauf et al., 2009a, 2009b). In the crystal packing of (I), intermolecular N—H···S H–bonds link the molecules into centrosymmetric dimers (Fig.2).

Related literature top

For background to our work on the

structural chemistry of N,N'-disubstituted thioures and for related structures, see: Khawer Rauf et al. (2009a,b). For bond-length data, see: Allen et al. (1987). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Freshly prepared benzoylisothiocyanate (1.63 g, 10 mmol) was dissolved in acetone (30 ml) and stirred for 30 minutes. Afterwards neat 4-n-butylaniline (1.49 g, 10 mmol) was added and the resulting mixture was stirred for 2 h. The reaction mixture was then poured into acidified water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:1 v/v) to give fine crystals of the title compound (I), with an overall yield of 95%.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009).

Figures top

	Fig. 1. ORTEP of (I). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds showns as dashed lines.
	Fig. 2. Packing diagram of (I). Hydrogen bonds shown as dashed lines.

1-Benzoyl-3-(4-n-butylphenyl)thiourea top

Crystal data top

C₁₈H₂₀N₂OS	Z = 2
M_r = 312.42	F(000) = 332
Triclinic, P1	D_x = 1.284 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 4.648 (3) Å	Cell parameters from 2558 reflections
b = 13.274 (8) Å	θ = 3.1–27.5°
c = 13.690 (8) Å	µ = 0.20 mm⁻¹
α = 106.765 (7)°	T = 123 K
β = 90.013 (6)°	Needle like, colorless
γ = 92.700 (8)°	0.40 × 0.10 × 0.10 mm
V = 807.9 (8) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3242 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.043
Graphite Monochromator monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 14.6199 pixels mm^-1	h = −6→3
dtintegrate.ref scans	k = −17→14
6380 measured reflections	l = −13→17
3632 independent reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0399P)² + 0.4308P] where P = (F_o² + 2F_c²)/3
3632 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₈H₂₀N₂OS	γ = 92.700 (8)°
M_r = 312.42	V = 807.9 (8) Å³
Triclinic, P1	Z = 2
a = 4.648 (3) Å	Mo Kα radiation
b = 13.274 (8) Å	µ = 0.20 mm⁻¹
c = 13.690 (8) Å	T = 123 K
α = 106.765 (7)°	0.40 × 0.10 × 0.10 mm
β = 90.013 (6)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3242 reflections with I > 2σ(I)
6380 measured reflections	R_int = 0.043
3632 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
3632 reflections	Δρ_min = −0.27 e Å⁻³
200 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.4183 (3)	0.19623 (11)	0.53711 (10)	0.0172 (3)
S1	0.33263 (9)	0.11726 (3)	0.60881 (3)	0.02424 (12)
N1	0.3191 (3)	0.29075 (10)	0.54395 (9)	0.0180 (3)
H1	0.3862	0.3194	0.4975	0.022*
N2	0.6153 (3)	0.16024 (10)	0.45859 (9)	0.0178 (3)
H2	0.6907	0.0999	0.4556	0.021*
C2	0.7060 (3)	0.20705 (12)	0.38572 (11)	0.0190 (3)
O1	0.6324 (3)	0.29449 (9)	0.38503 (9)	0.0271 (3)
C3	0.1241 (3)	0.35335 (11)	0.61301 (11)	0.0165 (3)
C4	−0.0402 (3)	0.32010 (12)	0.68386 (12)	0.0212 (3)
H4	−0.0285	0.2506	0.6890	0.025*
C5	−0.2219 (3)	0.39021 (13)	0.74715 (12)	0.0217 (3)
H5	−0.3322	0.3674	0.7959	0.026*
C6	−0.2477 (3)	0.49186 (12)	0.74157 (11)	0.0190 (3)
C7	−0.0851 (3)	0.52320 (12)	0.66869 (11)	0.0210 (3)
H7	−0.1008	0.5922	0.6624	0.025*
C8	0.0986 (3)	0.45522 (12)	0.60552 (11)	0.0201 (3)
H8	0.2083	0.4781	0.5566	0.024*
C9	−0.4331 (3)	0.56761 (13)	0.81559 (11)	0.0227 (3)
H9B	−0.6086	0.5291	0.8295	0.027*
H9A	−0.4937	0.6221	0.7845	0.027*
C10	−0.2717 (3)	0.62093 (13)	0.91620 (11)	0.0218 (3)
H10B	−0.2076	0.5659	0.9459	0.026*
H10A	−0.0976	0.6598	0.9017	0.026*
C11	−0.4509 (4)	0.69711 (14)	0.99458 (12)	0.0264 (3)
H11B	−0.5213	0.7509	0.9644	0.032*
H11A	−0.6208	0.6580	1.0117	0.032*
C12	−0.2805 (4)	0.75183 (15)	1.09179 (13)	0.0329 (4)
H12C	−0.2089	0.6989	1.1217	0.049*
H12A	−0.4055	0.7983	1.1406	0.049*
H12B	−0.1174	0.7935	1.0757	0.049*
C13	0.8938 (3)	0.14395 (12)	0.30440 (11)	0.0185 (3)
C14	0.9027 (3)	0.16959 (13)	0.21251 (12)	0.0247 (3)
H14	0.7984	0.2268	0.2049	0.030*
C15	1.0633 (4)	0.11182 (14)	0.13232 (12)	0.0281 (4)
H15	1.0667	0.1287	0.0695	0.034*
C16	1.2191 (4)	0.02936 (14)	0.14376 (12)	0.0275 (4)
H16	1.3290	−0.0102	0.0887	0.033*
C17	1.2152 (3)	0.00445 (13)	0.23512 (12)	0.0245 (3)
H17	1.3228	−0.0520	0.2428	0.029*
C18	1.0537 (3)	0.06196 (12)	0.31573 (11)	0.0190 (3)
H18	1.0526	0.0452	0.3787	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0203 (7)	0.0183 (7)	0.0122 (6)	0.0008 (5)	0.0007 (5)	0.0033 (5)
S1	0.0384 (2)	0.01744 (19)	0.0190 (2)	0.00574 (15)	0.01041 (15)	0.00803 (14)
N1	0.0224 (6)	0.0170 (6)	0.0155 (6)	0.0029 (5)	0.0043 (5)	0.0061 (5)
N2	0.0225 (6)	0.0157 (6)	0.0157 (6)	0.0036 (5)	0.0035 (5)	0.0050 (5)
C2	0.0219 (7)	0.0185 (7)	0.0172 (7)	0.0005 (5)	0.0018 (5)	0.0062 (6)
O1	0.0365 (6)	0.0215 (6)	0.0274 (6)	0.0072 (5)	0.0122 (5)	0.0130 (5)
C3	0.0179 (7)	0.0171 (7)	0.0136 (6)	0.0014 (5)	0.0001 (5)	0.0028 (5)
C4	0.0213 (7)	0.0205 (7)	0.0227 (7)	0.0013 (6)	0.0026 (6)	0.0078 (6)
C5	0.0209 (7)	0.0258 (8)	0.0189 (7)	0.0008 (6)	0.0038 (6)	0.0073 (6)
C6	0.0165 (7)	0.0227 (8)	0.0157 (7)	0.0019 (5)	−0.0034 (5)	0.0019 (6)
C7	0.0256 (8)	0.0178 (7)	0.0196 (7)	0.0039 (6)	−0.0004 (6)	0.0052 (6)
C8	0.0242 (7)	0.0214 (7)	0.0163 (7)	0.0016 (6)	0.0021 (5)	0.0078 (6)
C9	0.0202 (7)	0.0267 (8)	0.0188 (7)	0.0056 (6)	−0.0002 (6)	0.0020 (6)
C10	0.0198 (7)	0.0264 (8)	0.0172 (7)	0.0041 (6)	0.0012 (6)	0.0029 (6)
C11	0.0261 (8)	0.0318 (9)	0.0186 (8)	0.0060 (7)	0.0029 (6)	0.0023 (7)
C12	0.0399 (10)	0.0363 (10)	0.0180 (8)	0.0041 (8)	0.0022 (7)	0.0004 (7)
C13	0.0203 (7)	0.0189 (7)	0.0163 (7)	−0.0016 (5)	0.0020 (5)	0.0055 (6)
C14	0.0300 (8)	0.0260 (8)	0.0214 (8)	0.0048 (6)	0.0040 (6)	0.0116 (6)
C15	0.0361 (9)	0.0335 (9)	0.0161 (7)	0.0021 (7)	0.0052 (6)	0.0091 (7)
C16	0.0299 (8)	0.0286 (9)	0.0208 (8)	0.0022 (7)	0.0077 (6)	0.0020 (7)
C17	0.0241 (8)	0.0237 (8)	0.0250 (8)	0.0026 (6)	0.0032 (6)	0.0058 (6)
C18	0.0203 (7)	0.0203 (7)	0.0165 (7)	−0.0014 (6)	0.0005 (5)	0.0058 (6)

Geometric parameters (Å, º) top

C1—N1	1.335 (2)	C9—H9A	0.9900
C1—N2	1.4028 (19)	C10—C11	1.523 (2)
C1—S1	1.6659 (16)	C10—H10B	0.9900
N1—C3	1.4228 (18)	C10—H10A	0.9900
N1—H1	0.8800	C11—C12	1.521 (2)
N2—C2	1.3755 (19)	C11—H11B	0.9900
N2—H2	0.8800	C11—H11A	0.9900
C2—O1	1.2282 (19)	C12—H12C	0.9800
C2—C13	1.495 (2)	C12—H12A	0.9800
C3—C4	1.391 (2)	C12—H12B	0.9800
C3—C8	1.396 (2)	C13—C18	1.391 (2)
C4—C5	1.393 (2)	C13—C14	1.395 (2)
C4—H4	0.9500	C14—C15	1.386 (2)
C5—C6	1.384 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.386 (2)
C6—C7	1.397 (2)	C15—H15	0.9500
C6—C9	1.508 (2)	C16—C17	1.383 (2)
C7—C8	1.383 (2)	C16—H16	0.9500
C7—H7	0.9500	C17—C18	1.390 (2)
C8—H8	0.9500	C17—H17	0.9500
C9—C10	1.532 (2)	C18—H18	0.9500
C9—H9B	0.9900

N1—C1—N2	114.78 (12)	C11—C10—C9	113.76 (13)
N1—C1—S1	127.89 (11)	C11—C10—H10B	108.8
N2—C1—S1	117.32 (11)	C9—C10—H10B	108.8
C1—N1—C3	131.41 (13)	C11—C10—H10A	108.8
C1—N1—H1	114.3	C9—C10—H10A	108.8
C3—N1—H1	114.3	H10B—C10—H10A	107.7
C2—N2—C1	128.45 (13)	C12—C11—C10	112.35 (14)
C2—N2—H2	115.8	C12—C11—H11B	109.1
C1—N2—H2	115.8	C10—C11—H11B	109.1
O1—C2—N2	122.56 (14)	C12—C11—H11A	109.1
O1—C2—C13	121.20 (13)	C10—C11—H11A	109.1
N2—C2—C13	116.21 (13)	H11B—C11—H11A	107.9
C4—C3—C8	119.34 (13)	C11—C12—H12C	109.5
C4—C3—N1	125.23 (14)	C11—C12—H12A	109.5
C8—C3—N1	115.43 (13)	H12C—C12—H12A	109.5
C3—C4—C5	119.06 (14)	C11—C12—H12B	109.5
C3—C4—H4	120.5	H12C—C12—H12B	109.5
C5—C4—H4	120.5	H12A—C12—H12B	109.5
C6—C5—C4	122.41 (14)	C18—C13—C14	119.47 (14)
C6—C5—H5	118.8	C18—C13—C2	123.58 (13)
C4—C5—H5	118.8	C14—C13—C2	116.94 (14)
C5—C6—C7	117.70 (13)	C15—C14—C13	120.13 (15)
C5—C6—C9	120.87 (14)	C15—C14—H14	119.9
C7—C6—C9	121.34 (14)	C13—C14—H14	119.9
C8—C7—C6	120.92 (14)	C14—C15—C16	120.04 (15)
C8—C7—H7	119.5	C14—C15—H15	120.0
C6—C7—H7	119.5	C16—C15—H15	120.0
C7—C8—C3	120.55 (14)	C17—C16—C15	120.22 (15)
C7—C8—H8	119.7	C17—C16—H16	119.9
C3—C8—H8	119.7	C15—C16—H16	119.9
C6—C9—C10	111.53 (12)	C16—C17—C18	119.98 (15)
C6—C9—H9B	109.3	C16—C17—H17	120.0
C10—C9—H9B	109.3	C18—C17—H17	120.0
C6—C9—H9A	109.3	C17—C18—C13	120.14 (14)
C10—C9—H9A	109.3	C17—C18—H18	119.9
H9B—C9—H9A	108.0	C13—C18—H18	119.9

N2—C1—N1—C3	−178.89 (13)	N1—C3—C8—C7	179.89 (13)
S1—C1—N1—C3	2.0 (2)	C5—C6—C9—C10	83.10 (18)
N1—C1—N2—C2	−3.7 (2)	C7—C6—C9—C10	−93.57 (17)
S1—C1—N2—C2	175.53 (12)	C6—C9—C10—C11	−179.06 (14)
C1—N2—C2—O1	4.8 (2)	C9—C10—C11—C12	−177.71 (15)
C1—N2—C2—C13	−173.38 (13)	O1—C2—C13—C18	159.84 (15)
C1—N1—C3—C4	−9.2 (2)	N2—C2—C13—C18	−22.0 (2)
C1—N1—C3—C8	171.86 (14)	O1—C2—C13—C14	−20.9 (2)
C8—C3—C4—C5	−1.3 (2)	N2—C2—C13—C14	157.27 (14)
N1—C3—C4—C5	179.74 (14)	C18—C13—C14—C15	1.8 (2)
C3—C4—C5—C6	0.7 (2)	C2—C13—C14—C15	−177.51 (15)
C4—C5—C6—C7	0.5 (2)	C13—C14—C15—C16	−1.0 (3)
C4—C5—C6—C9	−176.28 (14)	C14—C15—C16—C17	−0.1 (3)
C5—C6—C7—C8	−1.0 (2)	C15—C16—C17—C18	0.2 (3)
C9—C6—C7—C8	175.77 (14)	C16—C17—C18—C13	0.6 (2)
C6—C7—C8—C3	0.3 (2)	C14—C13—C18—C17	−1.6 (2)
C4—C3—C8—C7	0.9 (2)	C2—C13—C18—C17	177.65 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.88	2.630 (2)	142
N2—H2···S1ⁱ	0.88	2.76	3.550 (2)	151

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂OS
M_r	312.42
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	4.648 (3), 13.274 (8), 13.690 (8)
α, β, γ (°)	106.765 (7), 90.013 (6), 92.700 (8)
V (Å³)	807.9 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6380, 3632, 3242
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.103, 1.06
No. of reflections	3632
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004), Yadokari-XG 2009 (Kabuto et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.88	2.630 (2)	142.0
N2—H2···S1ⁱ	0.88	2.76	3.550 (2)	150.6

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

MKR is grateful to the Quaid-i-Azam University, Islamabad, for financial support for a post-doctoral fellowship.

References

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