1-Benzoyl-3-(4-n-butyl-phen-yl)thio-urea.

The dihedral angle between the benzoyl and phenyl groups in the title compound, C(18)H(20)N(2)OS, 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

C18n class="CellLine">H20N2OS

M = 312.42

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.103

S = 1.06

3632 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051774/hg5142sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811051774/hg5142Isup3.cml

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

C18H20N2OS	Z = 2
Mr = 312.42	F(000) = 332
Triclinic, P1	Dx = 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

Rigaku/MSC Mercury CCD diffractometer	3242 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.043
Graphite Monochromator	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0399P)2 + 0.4308P] where P = (Fo2 + 2Fc2)/3
3632 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) .