N,N'-Diphenyl-thio-urea acetone monosolvate.

In the title compound, C(13)H(12)N(2)S·C(3)H(6)O, the phenyl rings of the thio-urea mol-ecule are in syn and anti positions in relation to the C=S bond. Two mol-ecules are connected by N-H⋯S=C hydrogen bonds into a centrosymmetric dimer. An additional N-H⋯O=C hydrogen bond to the acetone solvent mol-ecule and some weak C-H⋯π inter-actions reinforce the crystal structure.

Related literature

For the unsolvated N,N′-diphenyl­thio­urea stereoisomers, see: Ramnathan et al. (1995 ▶); Peseke et al. (1999 ▶). For the syn-syn-N,N′-diphenyl­thio­urea–dicyclo­hexyl-18-crown-6 co-crystal, see: Fonari et al. (2005 ▶). For related structures, see: Bowmaker et al. (2009 ▶); Okuniewski et al. (2010 ▶); Shen & Xu (2004 ▶).

Experimental

Crystal data

C13H12N2S·C3H6O

M = 286.38

Orthorhombic,

a = 17.1797 (6) Å

b = 10.0736 (4) Å

c = 17.4700 (7) Å

V = 3023.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 150 K

0.46 × 0.41 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.777, T max = 0.819

7549 measured reflections

3245 independent reflections

2278 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.092

S = 0.94

3245 reflections

191 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050300/ng5077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050300/ng5077Isup2.hkl

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

C13H12N2S·C3H6O	Dx = 1.258 Mg m−3
Mr = 286.38	Melting point: 154(1) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3367 reflections
a = 17.1797 (6) Å	θ = 2.3–28.7°
b = 10.0736 (4) Å	µ = 0.21 mm−1
c = 17.4700 (7) Å	T = 150 K
V = 3023.4 (2) Å3	Prism, clear colourless
Z = 8	0.46 × 0.41 × 0.27 mm
F(000) = 1216

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	2278 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 8.1883 pixels mm-1	θmax = 27°, θmin = 2.6°
ω scans	h = −9→21
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −7→12
Tmin = 0.777, Tmax = 0.819	l = −22→17
7549 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
3245 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.The phenyl rings centroids: Cg1 is the centroid of ring {C11,..,C16}: 0.22445 (4), 0.73429 (8), 0.46519 (4); Cg2 is the centroid of ring {C21,..,C26}: 0.06414 (4), 0.39968 (8), 0.17172 (4). Distance calculations were done using PLATON (Spek, 2009).

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 > 2σ(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	1.00623 (2)	0.60332 (4)	0.60875 (2)	0.02588 (12)
N1	0.90820 (7)	0.42124 (13)	0.56131 (7)	0.0227 (3)
H1	0.9367 (8)	0.4256 (17)	0.5206 (7)	0.033 (5)*
N2	0.89857 (8)	0.47225 (14)	0.68979 (7)	0.0245 (3)
H2	0.8677 (9)	0.4042 (13)	0.6956 (10)	0.040 (5)*
C1	0.93269 (8)	0.49352 (16)	0.62170 (8)	0.0219 (3)
C11	0.84080 (9)	0.34076 (16)	0.55234 (8)	0.0238 (3)
C12	0.84703 (10)	0.23117 (18)	0.50489 (8)	0.0292 (4)
H12	0.8963	0.207	0.4846	0.035*
C13	0.78192 (11)	0.1567 (2)	0.48687 (10)	0.0389 (5)
H13	0.7864	0.0819	0.454	0.047*
C14	0.71028 (11)	0.1916 (2)	0.51682 (10)	0.0406 (5)
H14	0.6653	0.1414	0.5042	0.049*
C15	0.70426 (9)	0.2990 (2)	0.56486 (10)	0.0358 (4)
H15	0.655	0.3215	0.586	0.043*
C16	0.76902 (9)	0.37509 (18)	0.58304 (9)	0.0291 (4)
H16	0.7643	0.4496	0.616	0.035*
C21	0.91899 (8)	0.53867 (17)	0.75969 (8)	0.0238 (4)
C22	0.91081 (9)	0.67464 (17)	0.76642 (9)	0.0285 (4)
H22	0.8934	0.7256	0.724	0.034*
C23	0.92812 (10)	0.73653 (19)	0.83536 (10)	0.0350 (4)
H23	0.9229	0.8301	0.84	0.042*
C24	0.95281 (10)	0.6625 (2)	0.89701 (9)	0.0376 (5)
H24	0.9645	0.7048	0.9442	0.045*
C25	0.96061 (11)	0.5259 (2)	0.88998 (9)	0.0371 (5)
H25	0.9775	0.4749	0.9326	0.045*
C26	0.94387 (9)	0.46364 (19)	0.82118 (8)	0.0305 (4)
H26	0.9495	0.3702	0.8164	0.037*
O1	0.79841 (7)	0.27541 (12)	0.76020 (7)	0.0398 (3)
C1A	0.80931 (9)	0.15731 (18)	0.76927 (9)	0.0273 (4)
C2	0.85919 (11)	0.0803 (2)	0.71495 (9)	0.0404 (5)
H2A	0.8556	0.1196	0.6638	0.061*
H2B	0.8413	−0.012	0.7131	0.061*
H2C	0.9134	0.0829	0.7324	0.061*
C3	0.77585 (10)	0.08360 (18)	0.83558 (9)	0.0328 (4)
H3A	0.7408	0.1422	0.8642	0.049*
H3B	0.818	0.0538	0.8692	0.049*
H3C	0.7467	0.0064	0.8169	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0267 (2)	0.0296 (2)	0.0214 (2)	−0.00829 (19)	0.00224 (15)	−0.00198 (18)
N1	0.0218 (6)	0.0268 (8)	0.0194 (6)	−0.0039 (6)	0.0019 (5)	−0.0024 (6)
N2	0.0279 (7)	0.0255 (8)	0.0200 (6)	−0.0065 (6)	0.0023 (5)	0.0005 (6)
C1	0.0222 (7)	0.0213 (8)	0.0222 (7)	0.0028 (7)	−0.0004 (6)	0.0007 (7)
C11	0.0266 (8)	0.0249 (9)	0.0199 (7)	−0.0051 (7)	−0.0018 (6)	0.0039 (7)
C12	0.0336 (8)	0.0284 (10)	0.0257 (8)	−0.0036 (8)	−0.0011 (7)	−0.0001 (8)
C13	0.0503 (11)	0.0336 (11)	0.0329 (9)	−0.0142 (9)	−0.0068 (8)	−0.0030 (9)
C14	0.0400 (10)	0.0423 (12)	0.0394 (10)	−0.0205 (10)	−0.0102 (8)	0.0107 (10)
C15	0.0253 (8)	0.0433 (12)	0.0388 (10)	−0.0074 (8)	0.0000 (7)	0.0113 (9)
C16	0.0268 (8)	0.0315 (10)	0.0289 (8)	−0.0016 (8)	0.0002 (6)	0.0014 (8)
C21	0.0215 (7)	0.0304 (9)	0.0196 (7)	−0.0055 (7)	0.0036 (6)	−0.0007 (7)
C22	0.0311 (9)	0.0295 (10)	0.0250 (8)	0.0003 (8)	0.0013 (6)	−0.0004 (8)
C23	0.0344 (9)	0.0341 (10)	0.0364 (9)	−0.0039 (8)	0.0050 (7)	−0.0106 (8)
C24	0.0355 (10)	0.0542 (13)	0.0230 (8)	−0.0118 (10)	0.0016 (7)	−0.0090 (9)
C25	0.0400 (10)	0.0494 (12)	0.0219 (8)	−0.0137 (10)	−0.0030 (7)	0.0092 (9)
C26	0.0330 (9)	0.0323 (10)	0.0264 (8)	−0.0075 (8)	−0.0011 (7)	0.0044 (8)
O1	0.0481 (8)	0.0297 (7)	0.0416 (7)	−0.0060 (6)	0.0094 (6)	0.0028 (6)
C1A	0.0249 (8)	0.0307 (10)	0.0263 (8)	−0.0053 (8)	−0.0050 (6)	−0.0019 (8)
C2	0.0403 (10)	0.0517 (13)	0.0292 (9)	0.0064 (10)	−0.0015 (7)	−0.0017 (9)
C3	0.0304 (9)	0.0352 (11)	0.0329 (9)	−0.0052 (8)	−0.0004 (7)	0.0065 (8)

S1—C1	1.6943 (16)	C21—C22	1.382 (2)
N1—C1	1.3492 (18)	C22—C23	1.388 (2)
N1—C11	1.4221 (19)	C22—H22	0.95
N1—H1	0.865 (9)	C23—C24	1.377 (3)
N2—C1	1.3433 (18)	C23—H23	0.95
N2—C21	1.4359 (19)	C24—C25	1.387 (3)
N2—H2	0.873 (9)	C24—H24	0.95
C11—C12	1.385 (2)	C25—C26	1.386 (2)
C11—C16	1.389 (2)	C25—H25	0.95
C12—C13	1.383 (2)	C26—H26	0.95
C12—H12	0.95	O1—C1A	1.215 (2)
C13—C14	1.383 (3)	C1A—C3	1.491 (2)
C13—H13	0.95	C1A—C2	1.495 (2)
C14—C15	1.373 (3)	C2—H2A	0.98
C14—H14	0.95	C2—H2B	0.98
C15—C16	1.388 (2)	C2—H2C	0.98
C15—H15	0.95	C3—H3A	0.98
C16—H16	0.95	C3—H3B	0.98
C21—C26	1.381 (2)	C3—H3C	0.98
C1—N1—C11	130.37 (13)	C21—C22—C23	119.81 (16)
C1—N1—H1	116.0 (11)	C21—C22—H22	120.1
C11—N1—H1	113.6 (11)	C23—C22—H22	120.1
C1—N2—C21	124.89 (14)	C24—C23—C22	120.07 (18)
C1—N2—H2	119.5 (12)	C24—C23—H23	120
C21—N2—H2	114.6 (11)	C22—C23—H23	120
N2—C1—N1	118.05 (14)	C23—C24—C25	119.85 (16)
N2—C1—S1	123.22 (11)	C23—C24—H24	120.1
N1—C1—S1	118.71 (11)	C25—C24—H24	120.1
C12—C11—C16	119.89 (15)	C26—C25—C24	120.37 (17)
C12—C11—N1	117.23 (14)	C26—C25—H25	119.8
C16—C11—N1	122.59 (15)	C24—C25—H25	119.8
C13—C12—C11	120.40 (16)	C21—C26—C25	119.40 (17)
C13—C12—H12	119.8	C21—C26—H26	120.3
C11—C12—H12	119.8	C25—C26—H26	120.3
C14—C13—C12	119.74 (18)	O1—C1A—C3	121.98 (16)
C14—C13—H13	120.1	O1—C1A—C2	120.89 (16)
C12—C13—H13	120.1	C3—C1A—C2	117.11 (16)
C15—C14—C13	119.91 (17)	C1A—C2—H2A	109.5
C15—C14—H14	120	C1A—C2—H2B	109.5
C13—C14—H14	120	H2A—C2—H2B	109.5
C14—C15—C16	120.98 (16)	C1A—C2—H2C	109.5
C14—C15—H15	119.5	H2A—C2—H2C	109.5
C16—C15—H15	119.5	H2B—C2—H2C	109.5
C15—C16—C11	119.07 (17)	C1A—C3—H3A	109.5
C15—C16—H16	120.5	C1A—C3—H3B	109.5
C11—C16—H16	120.5	H3A—C3—H3B	109.5
C26—C21—C22	120.50 (15)	C1A—C3—H3C	109.5
C26—C21—N2	118.82 (15)	H3A—C3—H3C	109.5
C22—C21—N2	120.62 (14)	H3B—C3—H3C	109.5

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.87 (1)	2.48 (1)	3.3240 (13)	165.(1)
N2—H2···O1	0.87 (1)	2.09 (1)	2.8993 (18)	154.(2)
C2—H2A···Cg1	0.98	3.02	3.931 (2)	155
C2—H2C···Cg2ii	0.98	2.80	3.607 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.87 (1)	2.48 (1)	3.3240 (13)	165 (1)
N2—H2⋯O1	0.87 (1)	2.09 (1)	2.8993 (18)	154 (2)
C2—H2A⋯Cg1	0.98	3.02	3.931 (2)	155
C2—H2C⋯Cg2ii	0.98	2.80	3.607 (2)	140

Symmetry codes: (i) ; (ii) .