1-(Naphthalen-1-yl)-3-[(thio-phen-2-yl)carbon-yl]thio-urea.

In the title compound, C(16)H(12)N(2)OS(2), the dihedral angles between the mean planes of the central thio-urea core and the thio-phene ring and the naphthalene ring system are 1.8 (2) and 6.45 (18)°, respectively. The mol-ecule adopts a trans-cis conformation with respect to the position of thio-phenoyl and naphthyl groups relative to the S atom across the thiourea C-N bonds. Both the thio-phene ring and the sulfanyl-idene S atom are disordered over two sets of sites with occupancies of 0.862 (3):0.138 (3) and 0.977 (3):0.023 (3), respectively. An intra-molecular N-H⋯O hydrogen bond is observed. The crystal packing features two N-H⋯S hydrogen bonds.

Related literature

For heterocyclic thiourea derivatives, metal complexes and their applications, see: D’hooghe et al. (2005 ▶); Aly et al. (2007 ▶); Estévez-Hernández et al. (2007 ▶); Saeed et al. (2008a ▶,b ▶,c ▶). For related structures, see: Singh et al. (2012 ▶); Koch (2001 ▶); Pérez et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).

Experimental

Crystal data

C16H12N2OS2

M = 312.40

Monoclinic,

a = 14.929 (2) Å

b = 5.9086 (8) Å

c = 17.071 (3) Å

β = 104.030 (14)°

V = 1460.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 173 K

0.35 × 0.25 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.712, T max = 1.000

4822 measured reflections

2625 independent reflections

1626 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.165

S = 1.09

2625 reflections

210 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812035350/bq2371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035350/bq2371Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035350/bq2371Isup3.cml

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

C16H12N2OS2	F(000) = 648
Mr = 312.40	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.929 (2) Å	Cell parameters from 1174 reflections
b = 5.9086 (8) Å	θ = 3.3–27.3°
c = 17.071 (3) Å	µ = 0.36 mm−1
β = 104.030 (14)°	T = 173 K
V = 1460.9 (4) Å3	Prism, colorless
Z = 4	0.35 × 0.25 × 0.15 mm

Oxford Diffraction Xcalibur Eos diffractometer	2625 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 16.0938 pixels mm-1	θmax = 25.5°, θmin = 3.7°
ω scans	h = −18→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −6→7
Tmin = 0.712, Tmax = 1.000	l = −17→20
4822 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.058P)2 + 0.3695P] where P = (Fo2 + 2Fc2)/3
2625 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.33 e Å−3
10 restraints	Δρmin = −0.31 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	Occ. (<1)
S1A	0.962 (3)	0.732 (11)	0.421 (4)	0.0764 (5)	0.023 (3)
S1B	0.98334 (7)	0.6323 (3)	0.38685 (9)	0.0764 (5)	0.977 (3)
S2A	0.66455 (8)	−0.0348 (2)	0.46547 (8)	0.0582 (4)	0.862 (3)
C13A	0.7707 (3)	0.0902 (7)	0.4715 (3)	0.0404 (11)	0.862 (3)
C14A	0.8378 (4)	−0.0413 (13)	0.5210 (5)	0.0655 (19)	0.862 (3)
H14A	0.9018	−0.0083	0.5310	0.079*	0.862 (3)
C15A	0.8041 (4)	−0.2228 (11)	0.5543 (4)	0.0655 (15)	0.862 (3)
H15A	0.8419	−0.3270	0.5900	0.079*	0.862 (3)
C16A	0.7114 (4)	−0.2380 (12)	0.5309 (6)	0.0695 (14)	0.862 (3)
H16A	0.6765	−0.3515	0.5496	0.083*	0.862 (3)
S2B	0.8612 (8)	−0.036 (2)	0.5239 (9)	0.0582 (4)	0.138 (3)
C13B	0.7593 (17)	0.051 (5)	0.4590 (19)	0.0404 (11)	0.138 (3)
C14B	0.6895 (17)	−0.046 (5)	0.488 (2)	0.0655 (19)	0.138 (3)
H14B	0.6294	0.0174	0.4803	0.079*	0.138 (3)
C15B	0.716 (2)	−0.242 (7)	0.530 (4)	0.0655 (15)	0.138 (3)
H15B	0.6767	−0.3658	0.5338	0.079*	0.138 (3)
C16B	0.807 (2)	−0.233 (7)	0.566 (3)	0.0695 (14)	0.138 (3)
H16B	0.8373	−0.3273	0.6097	0.083*	0.138 (3)
O1	0.69721 (14)	0.3590 (3)	0.37691 (14)	0.0546 (6)
N1	0.79871 (16)	0.6726 (4)	0.33310 (16)	0.0440 (7)
H1A	0.7462	0.6094	0.3360	0.053*
N2	0.85320 (16)	0.3884 (4)	0.42315 (16)	0.0452 (7)
H2A	0.9009	0.3300	0.4579	0.054*
C1	0.7879 (2)	0.8627 (5)	0.28085 (19)	0.0432 (8)
C2	0.8584 (2)	1.0074 (5)	0.2753 (2)	0.0541 (9)
H2	0.9196	0.9774	0.3054	0.065*
C3	0.8401 (3)	1.1985 (5)	0.2255 (2)	0.0585 (10)
H3	0.8894	1.2973	0.2223	0.070*
C4	0.7537 (3)	1.2454 (5)	0.1817 (2)	0.0570 (9)
H4	0.7429	1.3778	0.1492	0.068*
C5	0.6798 (2)	1.0997 (5)	0.1838 (2)	0.0468 (8)
C6	0.5901 (3)	1.1427 (6)	0.1368 (2)	0.0594 (10)
H6	0.5788	1.2741	0.1038	0.071*
C7	0.5189 (3)	0.9981 (6)	0.1379 (2)	0.0659 (11)
H7	0.4587	1.0297	0.1060	0.079*
C8	0.5347 (2)	0.8048 (6)	0.1857 (2)	0.0574 (10)
H8	0.4851	0.7044	0.1859	0.069*
C9	0.6200 (2)	0.7578 (5)	0.2319 (2)	0.0494 (9)
H9	0.6291	0.6249	0.2642	0.059*
C10	0.6962 (2)	0.9031 (5)	0.23326 (19)	0.0416 (8)
C11	0.8727 (2)	0.5719 (5)	0.37841 (19)	0.0434 (8)
C12	0.7696 (2)	0.2864 (5)	0.4203 (2)	0.0433 (8)

	U11	U22	U33	U12	U13	U23
S1A	0.0282 (5)	0.1166 (10)	0.0801 (9)	−0.0049 (6)	0.0048 (5)	0.0291 (8)
S1B	0.0282 (5)	0.1166 (10)	0.0801 (9)	−0.0049 (6)	0.0048 (5)	0.0291 (8)
S2A	0.0543 (7)	0.0566 (6)	0.0598 (9)	−0.0107 (6)	0.0061 (5)	0.0071 (6)
C13A	0.0405 (19)	0.035 (2)	0.041 (2)	−0.0003 (16)	0.0015 (16)	−0.0068 (18)
C14A	0.057 (4)	0.064 (3)	0.077 (4)	0.000 (3)	0.020 (4)	−0.010 (2)
C15A	0.091 (4)	0.048 (2)	0.051 (3)	0.023 (3)	0.004 (3)	0.006 (2)
C16A	0.090 (4)	0.053 (3)	0.063 (3)	−0.015 (3)	0.015 (3)	0.002 (2)
S2B	0.0543 (7)	0.0566 (6)	0.0598 (9)	−0.0107 (6)	0.0061 (5)	0.0071 (6)
C13B	0.0405 (19)	0.035 (2)	0.041 (2)	−0.0003 (16)	0.0015 (16)	−0.0068 (18)
C14B	0.057 (4)	0.064 (3)	0.077 (4)	0.000 (3)	0.020 (4)	−0.010 (2)
C15B	0.091 (4)	0.048 (2)	0.051 (3)	0.023 (3)	0.004 (3)	0.006 (2)
C16B	0.090 (4)	0.053 (3)	0.063 (3)	−0.015 (3)	0.015 (3)	0.002 (2)
O1	0.0340 (12)	0.0537 (13)	0.0694 (16)	−0.0034 (10)	−0.0006 (11)	0.0150 (12)
N1	0.0286 (13)	0.0453 (14)	0.0541 (17)	−0.0030 (11)	0.0021 (12)	0.0007 (13)
N2	0.0302 (13)	0.0547 (15)	0.0472 (16)	0.0030 (12)	0.0026 (11)	0.0113 (13)
C1	0.0381 (17)	0.0383 (15)	0.0503 (19)	−0.0019 (14)	0.0050 (14)	−0.0047 (14)
C2	0.0455 (19)	0.0503 (18)	0.067 (2)	−0.0095 (16)	0.0136 (17)	−0.0035 (17)
C3	0.063 (2)	0.0504 (18)	0.068 (2)	−0.0188 (18)	0.0281 (19)	−0.0075 (18)
C4	0.072 (2)	0.0452 (17)	0.059 (2)	−0.0030 (19)	0.0254 (19)	0.0032 (16)
C5	0.0516 (19)	0.0406 (16)	0.050 (2)	0.0058 (16)	0.0165 (16)	−0.0023 (15)
C6	0.062 (2)	0.057 (2)	0.059 (2)	0.0175 (19)	0.0146 (19)	0.0156 (18)
C7	0.051 (2)	0.075 (2)	0.067 (3)	0.018 (2)	0.0062 (19)	0.017 (2)
C8	0.0409 (19)	0.064 (2)	0.065 (2)	0.0007 (17)	0.0078 (17)	0.0111 (19)
C9	0.0421 (18)	0.0506 (17)	0.052 (2)	−0.0010 (16)	0.0044 (15)	0.0080 (16)
C10	0.0387 (17)	0.0380 (15)	0.0477 (19)	0.0024 (14)	0.0092 (14)	−0.0061 (14)
C11	0.0342 (16)	0.0593 (18)	0.0356 (17)	−0.0004 (15)	0.0065 (13)	0.0002 (15)
C12	0.0322 (16)	0.0423 (16)	0.0513 (19)	0.0028 (14)	0.0023 (14)	−0.0017 (15)

S1A—C11	1.65 (5)	N1—H1A	0.8800
S1B—C11	1.661 (3)	N2—C12	1.376 (4)
S2A—C16A	1.674 (6)	N2—C11	1.397 (4)
S2A—C13A	1.729 (4)	N2—H2A	0.8800
C13A—C14A	1.383 (7)	C1—C2	1.377 (4)
C13A—C12	1.449 (5)	C1—C10	1.432 (4)
C14A—C15A	1.365 (8)	C2—C3	1.401 (5)
C14A—H14A	0.9500	C2—H2	0.9500
C15A—C16A	1.347 (6)	C3—C4	1.353 (5)
C15A—H15A	0.9500	C3—H3	0.9500
C16A—H16A	0.9500	C4—C5	1.408 (5)
S2B—C16B	1.67 (2)	C4—H4	0.9500
S2B—C13B	1.728 (19)	C5—C6	1.407 (4)
C13B—C14B	1.39 (2)	C5—C10	1.422 (4)
C13B—C12	1.56 (3)	C6—C7	1.367 (5)
C14B—C15B	1.37 (2)	C6—H6	0.9500
C14B—H14B	0.9500	C7—C8	1.390 (5)
C15B—C16B	1.350 (18)	C7—H7	0.9500
C15B—H15B	0.9500	C8—C9	1.354 (4)
C16B—H16B	0.9500	C8—H8	0.9500
O1—C12	1.230 (3)	C9—C10	1.421 (4)
N1—C11	1.326 (4)	C9—H9	0.9500
N1—C1	1.419 (4)
C16A—S2A—C13A	92.2 (2)	C3—C2—H2	119.9
C14A—C13A—C12	136.0 (5)	C4—C3—C2	121.3 (3)
C14A—C13A—S2A	108.3 (4)	C4—C3—H3	119.3
C12—C13A—S2A	115.4 (3)	C2—C3—H3	119.3
C15A—C14A—C13A	114.2 (5)	C3—C4—C5	120.6 (3)
C15A—C14A—H14A	122.9	C3—C4—H4	119.7
C13A—C14A—H14A	122.9	C5—C4—H4	119.7
C16A—C15A—C14A	112.6 (5)	C4—C5—C6	121.3 (3)
C16A—C15A—H15A	123.7	C4—C5—C10	119.4 (3)
C14A—C15A—H15A	123.7	C6—C5—C10	119.3 (3)
C15A—C16A—S2A	112.5 (5)	C7—C6—C5	121.0 (3)
C15A—C16A—H16A	123.7	C7—C6—H6	119.5
S2A—C16A—H16A	123.7	C5—C6—H6	119.5
C16B—S2B—C13B	92.5 (12)	C6—C7—C8	119.9 (3)
C14B—C13B—C12	133 (2)	C6—C7—H7	120.0
C14B—C13B—S2B	105.6 (15)	C8—C7—H7	120.0
C12—C13B—S2B	112.0 (16)	C9—C8—C7	120.8 (3)
C15B—C14B—C13B	113 (2)	C9—C8—H8	119.6
C15B—C14B—H14B	123.6	C7—C8—H8	119.6
C13B—C14B—H14B	123.6	C8—C9—C10	121.4 (3)
C16B—C15B—C14B	110 (2)	C8—C9—H9	119.3
C16B—C15B—H15B	125.2	C10—C9—H9	119.3
C14B—C15B—H15B	125.2	C9—C10—C5	117.5 (3)
C15B—C16B—S2B	112 (2)	C9—C10—C1	124.0 (3)
C15B—C16B—H16B	124.2	C5—C10—C1	118.5 (3)
S2B—C16B—H16B	124.2	N1—C11—N2	114.4 (3)
C11—N1—C1	132.4 (3)	N1—C11—S1A	118 (2)
C11—N1—H1A	113.8	N2—C11—S1A	117.1 (18)
C1—N1—H1A	113.8	N1—C11—S1B	128.6 (3)
C12—N2—C11	128.9 (2)	N2—C11—S1B	117.0 (2)
C12—N2—H2A	115.5	S1A—C11—S1B	33 (3)
C11—N2—H2A	115.5	O1—C12—N2	121.7 (3)
C2—C1—N1	124.2 (3)	O1—C12—C13A	121.5 (3)
C2—C1—C10	119.9 (3)	N2—C12—C13A	116.8 (3)
N1—C1—C10	115.9 (3)	O1—C12—C13B	113.8 (9)
C1—C2—C3	120.2 (3)	N2—C12—C13B	123.8 (9)
C1—C2—H2	119.9	C13A—C12—C13B	11.9 (13)
C16A—S2A—C13A—C14A	3.3 (6)	C4—C5—C10—C9	−178.4 (3)
C16A—S2A—C13A—C12	178.1 (5)	C6—C5—C10—C9	0.4 (5)
C12—C13A—C14A—C15A	−176.1 (6)	C4—C5—C10—C1	1.4 (4)
S2A—C13A—C14A—C15A	−2.9 (8)	C6—C5—C10—C1	−179.8 (3)
C13A—C14A—C15A—C16A	0.8 (11)	C2—C1—C10—C9	176.9 (3)
C14A—C15A—C16A—S2A	1.9 (11)	N1—C1—C10—C9	−4.5 (5)
C13A—S2A—C16A—C15A	−3.0 (8)	C2—C1—C10—C5	−2.8 (5)
C16B—S2B—C13B—C14B	13 (4)	N1—C1—C10—C5	175.8 (3)
C16B—S2B—C13B—C12	164 (3)	C1—N1—C11—N2	178.7 (3)
C12—C13B—C14B—C15B	−169 (4)	C1—N1—C11—S1A	35 (3)
S2B—C13B—C14B—C15B	−27 (5)	C1—N1—C11—S1B	−2.6 (5)
C13B—C14B—C15B—C16B	30 (6)	C12—N2—C11—N1	7.1 (5)
C14B—C15B—C16B—S2B	−19 (7)	C12—N2—C11—S1A	151 (3)
C13B—S2B—C16B—C15B	3 (5)	C12—N2—C11—S1B	−171.6 (3)
C11—N1—C1—C2	−9.6 (5)	C11—N2—C12—O1	−3.4 (5)
C11—N1—C1—C10	171.8 (3)	C11—N2—C12—C13A	177.1 (3)
N1—C1—C2—C3	−176.2 (3)	C11—N2—C12—C13B	165.9 (17)
C10—C1—C2—C3	2.3 (5)	C14A—C13A—C12—O1	174.0 (6)
C1—C2—C3—C4	−0.2 (5)	S2A—C13A—C12—O1	1.2 (5)
C2—C3—C4—C5	−1.3 (5)	C14A—C13A—C12—N2	−6.5 (8)
C3—C4—C5—C6	−178.1 (3)	S2A—C13A—C12—N2	−179.4 (3)
C3—C4—C5—C10	0.7 (5)	C14A—C13A—C12—C13B	122 (7)
C4—C5—C6—C7	178.6 (4)	S2A—C13A—C12—C13B	−51 (6)
C10—C5—C6—C7	−0.2 (5)	C14B—C13B—C12—O1	−36 (4)
C5—C6—C7—C8	−0.3 (6)	S2B—C13B—C12—O1	−176.6 (15)
C6—C7—C8—C9	0.4 (6)	C14B—C13B—C12—N2	154 (3)
C7—C8—C9—C10	−0.2 (5)	S2B—C13B—C12—N2	13 (3)
C8—C9—C10—C5	−0.3 (5)	C14B—C13B—C12—C13A	96 (9)
C8—C9—C10—C1	180.0 (3)	S2B—C13B—C12—C13A	−44 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.86	2.615 (3)	143
N2—H2A···S2B	0.88	2.57	3.026 (14)	113
N2—H2A···S1Ai	0.88	2.56	3.41 (4)	164
N2—H2A···S1Bi	0.88	2.80	3.557 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.88	1.86	2.615 (3)	143
N2—H2A⋯S2B	0.88	2.57	3.026 (14)	113
N2—H2A⋯S1A i	0.88	2.56	3.41 (4)	164
N2—H2A⋯S1B i	0.88	2.80	3.557 (3)	145

Symmetry code: (i) .