1-Benzoyl-3-(naphthalen-1-yl)thio-urea.

In the title compound, C(18)H(14)N(2)OS, the dihedral angle between the mean planes of the 3-naphthyl and 1-benzoyl rings is 20.7 (1)°. The crystal packing is stabilized by weak N-H⋯S inter-actions. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonding is also observed.

Related literature

For the biological activity of thio­urea in medicinal chemistry, see: Saeed et al. (2009 ▶, 2010a ▶,b ▶); Maddani & Prabhu (2010 ▶). For the use of thio­urea derivatives in organocatalysis, see: Jung & Kim (2008 ▶) and for their use as curing agents for ep­oxy resins, see: Saeed et al. (2011 ▶). For the use of thio­ureas as ligands in coordination chemistry, see: Burrows et al. (1999 ▶); Henderson et al. (2002 ▶); Schuster et al. (1990 ▶). For the pesticidal activity of acyl thio­ureas, see: Che et al. (1999 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C18H14N2OS

M = 306.37

Monoclinic,

a = 9.7368 (14) Å

b = 5.2256 (10) Å

c = 28.619 (4) Å

β = 92.126 (12)°

V = 1455.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.35 × 0.08 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.925, T max = 0.982

12731 measured reflections

3460 independent reflections

2206 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.135

S = 1.05

3460 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104582X/fk2043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104582X/fk2043Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104582X/fk2043Isup3.cml

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

C18H14N2OS	F(000) = 640
Mr = 306.37	Dx = 1.398 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1307 reflections
a = 9.7368 (14) Å	θ = 3.5–32.3°
b = 5.2256 (10) Å	µ = 0.23 mm−1
c = 28.619 (4) Å	T = 173 K
β = 92.126 (12)°	Rod, colourless
V = 1455.2 (4) Å3	0.35 × 0.08 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3460 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2206 reflections with I > 2σ(I)
graphite	Rint = 0.082
Detector resolution: 16.1500 pixels mm-1	θmax = 27.9°, θmin = 4.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.925, Tmax = 0.982	l = −34→37
12731 measured 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.1745P] where P = (Fo2 + 2Fc2)/3
3460 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

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..

	x	y	z	Uiso*/Ueq
S1	0.63172 (7)	0.32704 (17)	0.54848 (3)	0.0446 (2)
O1	0.28206 (18)	0.5576 (4)	0.63936 (6)	0.0395 (5)
N1	0.4117 (2)	0.5657 (4)	0.57512 (7)	0.0300 (5)
H1	0.423 (3)	0.632 (5)	0.5480 (7)	0.036*
N2	0.4889 (2)	0.2542 (4)	0.62654 (7)	0.0280 (5)
H2	0.421 (2)	0.315 (5)	0.6413 (9)	0.034*
C1	0.2515 (3)	1.0084 (5)	0.54374 (9)	0.0313 (6)
H1A	0.3367	0.9825	0.5293	0.038*
C2	0.1632 (3)	1.1966 (5)	0.52738 (10)	0.0413 (7)
H2A	0.1872	1.2993	0.5016	0.050*
C3	0.0399 (3)	1.2359 (6)	0.54847 (11)	0.0427 (7)
H3A	−0.0216	1.3642	0.5369	0.051*
C4	0.0059 (3)	1.0899 (6)	0.58617 (10)	0.0407 (7)
H4A	−0.0784	1.1195	0.6010	0.049*
C5	0.0929 (3)	0.9015 (5)	0.60260 (10)	0.0364 (7)
H5A	0.0685	0.8010	0.6287	0.044*
C6	0.2167 (2)	0.8566 (5)	0.58122 (8)	0.0257 (5)
C7	0.3049 (2)	0.6496 (5)	0.60124 (8)	0.0272 (6)
C8	0.5082 (2)	0.3745 (5)	0.58638 (9)	0.0292 (6)
C9	0.5611 (2)	0.0543 (5)	0.64982 (9)	0.0268 (6)
C10	0.6612 (2)	−0.0889 (5)	0.62991 (9)	0.0331 (6)
H10A	0.6876	−0.0526	0.5990	0.040*
C11	0.7248 (3)	−0.2889 (6)	0.65515 (10)	0.0395 (7)
H11A	0.7964	−0.3833	0.6415	0.047*
C12	0.6859 (3)	−0.3498 (5)	0.69861 (10)	0.0379 (7)
H12A	0.7289	−0.4890	0.7147	0.046*
C13	0.5827 (2)	−0.2094 (5)	0.72029 (9)	0.0297 (6)
C14	0.5195 (2)	−0.0002 (5)	0.69628 (8)	0.0261 (5)
C15	0.4192 (2)	0.1399 (5)	0.71991 (9)	0.0306 (6)
H15A	0.3758	0.2818	0.7048	0.037*
C16	0.3832 (3)	0.0759 (5)	0.76395 (9)	0.0354 (7)
H16A	0.3159	0.1740	0.7791	0.043*
C17	0.4444 (3)	−0.1323 (5)	0.78703 (9)	0.0371 (7)
H17A	0.4181	−0.1770	0.8176	0.045*
C18	0.5413 (3)	−0.2703 (5)	0.76558 (9)	0.0339 (6)
H18A	0.5826	−0.4119	0.7815	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0376 (4)	0.0694 (6)	0.0275 (4)	0.0166 (4)	0.0126 (3)	0.0087 (4)
O1	0.0407 (11)	0.0504 (12)	0.0283 (11)	0.0153 (10)	0.0124 (8)	0.0099 (9)
N1	0.0283 (11)	0.0381 (13)	0.0239 (12)	0.0030 (10)	0.0044 (9)	0.0055 (10)
N2	0.0248 (11)	0.0373 (13)	0.0223 (11)	0.0044 (10)	0.0066 (9)	0.0002 (9)
C1	0.0320 (14)	0.0316 (15)	0.0304 (15)	−0.0021 (12)	0.0043 (11)	−0.0020 (12)
C2	0.0535 (18)	0.0349 (16)	0.0356 (16)	0.0020 (14)	0.0032 (14)	0.0069 (13)
C3	0.0403 (16)	0.0390 (17)	0.0485 (19)	0.0075 (14)	−0.0042 (14)	0.0044 (14)
C4	0.0312 (15)	0.0450 (18)	0.0460 (18)	0.0060 (14)	0.0049 (13)	0.0053 (14)
C5	0.0315 (14)	0.0396 (17)	0.0384 (16)	0.0038 (13)	0.0063 (12)	0.0069 (13)
C6	0.0249 (13)	0.0277 (14)	0.0245 (13)	−0.0005 (11)	0.0015 (10)	−0.0014 (11)
C7	0.0261 (13)	0.0317 (14)	0.0241 (13)	−0.0010 (11)	0.0055 (10)	−0.0017 (11)
C8	0.0233 (13)	0.0381 (16)	0.0260 (14)	0.0033 (12)	0.0009 (10)	−0.0009 (12)
C9	0.0237 (12)	0.0276 (14)	0.0289 (14)	−0.0001 (11)	0.0003 (10)	−0.0024 (11)
C10	0.0285 (14)	0.0390 (16)	0.0319 (15)	0.0033 (12)	0.0017 (11)	−0.0021 (12)
C11	0.0312 (15)	0.0408 (17)	0.0463 (18)	0.0070 (13)	−0.0002 (13)	−0.0087 (14)
C12	0.0376 (15)	0.0348 (16)	0.0409 (17)	0.0019 (13)	−0.0050 (13)	0.0004 (13)
C13	0.0276 (13)	0.0270 (14)	0.0340 (15)	−0.0040 (11)	−0.0040 (11)	−0.0003 (11)
C14	0.0258 (13)	0.0260 (13)	0.0263 (14)	−0.0058 (11)	−0.0010 (10)	−0.0011 (10)
C15	0.0305 (14)	0.0312 (14)	0.0301 (14)	0.0025 (12)	0.0022 (11)	0.0024 (11)
C16	0.0394 (15)	0.0372 (16)	0.0302 (15)	0.0005 (13)	0.0074 (12)	0.0024 (12)
C17	0.0410 (16)	0.0426 (17)	0.0279 (15)	−0.0078 (14)	0.0029 (12)	0.0076 (13)
C18	0.0381 (15)	0.0286 (14)	0.0342 (15)	−0.0080 (13)	−0.0083 (12)	0.0053 (12)

S1—C8	1.667 (2)	C6—C7	1.483 (3)
O1—C7	1.220 (3)	C9—C10	1.370 (3)
N1—C7	1.375 (3)	C9—C14	1.433 (3)
N1—C8	1.401 (3)	C10—C11	1.401 (4)
N1—H1	0.859 (16)	C10—H10A	0.9500
N2—C8	1.329 (3)	C11—C12	1.351 (4)
N2—C9	1.412 (3)	C11—H11A	0.9500
N2—H2	0.861 (16)	C12—C13	1.407 (4)
C1—C2	1.377 (4)	C12—H12A	0.9500
C1—C6	1.386 (3)	C13—C18	1.408 (4)
C1—H1A	0.9500	C13—C14	1.419 (3)
C2—C3	1.379 (4)	C14—C15	1.413 (3)
C2—H2A	0.9500	C15—C16	1.362 (3)
C3—C4	1.372 (4)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.395 (4)
C4—C5	1.370 (4)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.353 (4)
C5—C6	1.392 (3)	C17—H17A	0.9500
C5—H5A	0.9500	C18—H18A	0.9500
C7—N1—C8	128.1 (2)	C10—C9—N2	123.9 (2)
C7—N1—H1	119.1 (18)	C10—C9—C14	120.5 (2)
C8—N1—H1	112.8 (18)	N2—C9—C14	115.6 (2)
C8—N2—C9	132.4 (2)	C9—C10—C11	120.0 (3)
C8—N2—H2	112.6 (18)	C9—C10—H10A	120.0
C9—N2—H2	115.0 (18)	C11—C10—H10A	120.0
C2—C1—C6	120.3 (2)	C12—C11—C10	121.1 (3)
C2—C1—H1A	119.9	C12—C11—H11A	119.5
C6—C1—H1A	119.9	C10—C11—H11A	119.5
C1—C2—C3	120.1 (3)	C11—C12—C13	120.8 (3)
C1—C2—H2A	120.0	C11—C12—H12A	119.6
C3—C2—H2A	120.0	C13—C12—H12A	119.6
C4—C3—C2	120.0 (3)	C12—C13—C18	121.4 (2)
C4—C3—H3A	120.0	C12—C13—C14	119.5 (2)
C2—C3—H3A	120.0	C18—C13—C14	119.1 (2)
C5—C4—C3	120.4 (3)	C15—C14—C13	117.5 (2)
C5—C4—H4A	119.8	C15—C14—C9	124.4 (2)
C3—C4—H4A	119.8	C13—C14—C9	118.1 (2)
C4—C5—C6	120.3 (3)	C16—C15—C14	121.4 (2)
C4—C5—H5A	119.9	C16—C15—H15A	119.3
C6—C5—H5A	119.9	C14—C15—H15A	119.3
C1—C6—C5	119.0 (2)	C15—C16—C17	120.7 (3)
C1—C6—C7	124.2 (2)	C15—C16—H16A	119.7
C5—C6—C7	116.8 (2)	C17—C16—H16A	119.7
O1—C7—N1	121.8 (2)	C18—C17—C16	119.6 (3)
O1—C7—C6	120.7 (2)	C18—C17—H17A	120.2
N1—C7—C6	117.5 (2)	C16—C17—H17A	120.2
N2—C8—N1	114.9 (2)	C17—C18—C13	121.7 (3)
N2—C8—S1	128.4 (2)	C17—C18—H18A	119.2
N1—C8—S1	116.76 (19)	C13—C18—H18A	119.2
C6—C1—C2—C3	0.4 (4)	C14—C9—C10—C11	−0.6 (4)
C1—C2—C3—C4	0.9 (5)	C9—C10—C11—C12	2.2 (4)
C2—C3—C4—C5	−1.1 (5)	C10—C11—C12—C13	−1.7 (4)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—C18	−179.9 (2)
C2—C1—C6—C5	−1.5 (4)	C11—C12—C13—C14	−0.5 (4)
C2—C1—C6—C7	180.0 (2)	C12—C13—C14—C15	−178.2 (2)
C4—C5—C6—C1	1.2 (4)	C18—C13—C14—C15	1.2 (3)
C4—C5—C6—C7	179.9 (2)	C12—C13—C14—C9	2.0 (3)
C8—N1—C7—O1	−0.4 (4)	C18—C13—C14—C9	−178.6 (2)
C8—N1—C7—C6	180.0 (2)	C10—C9—C14—C15	178.8 (2)
C1—C6—C7—O1	165.4 (3)	N2—C9—C14—C15	−3.5 (4)
C5—C6—C7—O1	−13.2 (4)	C10—C9—C14—C13	−1.5 (3)
C1—C6—C7—N1	−15.0 (4)	N2—C9—C14—C13	176.2 (2)
C5—C6—C7—N1	166.4 (2)	C13—C14—C15—C16	−0.5 (4)
C9—N2—C8—N1	179.7 (2)	C9—C14—C15—C16	179.2 (2)
C9—N2—C8—S1	−0.6 (4)	C14—C15—C16—C17	−0.4 (4)
C7—N1—C8—N2	3.1 (4)	C15—C16—C17—C18	0.7 (4)
C7—N1—C8—S1	−176.7 (2)	C16—C17—C18—C13	0.0 (4)
C8—N2—C9—C10	−10.9 (4)	C12—C13—C18—C17	178.4 (3)
C8—N2—C9—C14	171.5 (3)	C14—C13—C18—C17	−0.9 (4)
N2—C9—C10—C11	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	1.85 (2)	2.600 (3)	144 (2)
N1—H1···S1i	0.86 (2)	2.80 (2)	3.591 (2)	153 (2)
C15—H15A···O1	0.95	2.51	3.411 (3)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (2)	1.85 (2)	2.600 (3)	144 (2)
N1—H1⋯S1i	0.86 (2)	2.80 (2)	3.591 (2)	153 (2)
C15—H15A⋯O1	0.95	2.51	3.411 (3)	159

Symmetry code: (i) .