N,N′-Diphenyl­thio­urea acetone monosolvate

Okuniewski, A.; Chojnacki, J.; Becker, B.

doi:10.1107/S1600536810050300

organic compounds

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Volume 67| Part 1| January 2011| Page o55

https://doi.org/10.1107/S1600536810050300

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N,N′-Diphenylthiourea acetone monosolvate

Andrzej Okuniewski,^a Jaroslaw Chojnacki ^a and Barbara Becker ^a ^*

^aDepartment of Inorganic Chemistry, Gdansk University of Technology, 11/12 Narutowicza Str., 80-233 Gdańsk, Poland
^*Correspondence e-mail: barbara.becker@pg.gda.pl

(Received 25 November 2010; accepted 1 December 2010; online 8 December 2010)

In the title compound, C₁₃H₁₂N₂S·C₃H₆O, the phenyl rings of the thiourea molecule are in syn and anti positions in relation to the C=S bond. Two molecules 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 molecule and some weak C—H⋯π interactions 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_r = 286.38
Orthorhombic, P b c a
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.092
S = 0.94
3245 reflections
191 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050300/ng5077Isup2.hkl

checkCIF report

Comment top

N,N'-Diphenylthiourea (thiocarbanilide), S═C(NHPh)₂, is commonly used as rubber vulcanization accelerator and as a stabilizer for PVC and PVDC. X-ray structures of its two possible stereoisomers have been already determined. The first is syn-syn isomer (Ramnathan et al., 1995), where only weak R₂¹(6) bifurcative N—H···S hydrogen bonds are present. The second – syn-anti isomer (Peseke et al., 1999) – is more stable because of dimer formation. Two N—H···S hydrogen bonds form R₂²(8) centrosymmetric structural motif. There are also some π···π and N—H···π interactions.

CSD 5.32 contains data on 15 structures of N,N'-diphenylthiourea and its complexes. Syn-anti isomer is more common (12 cases). Syn-syn isomer is present in the single-component crystal (Ramnathan et al., 1995), as a cocrystal with dicyclohexyl-18-crown-6 (Fonari et al., 2005) and as a copper(I) complex (Bowmaker et al., 2009).

When N,N'-diphenylthiourea cocrystalizes with acetone in Pbca space group the centrosymmetric dimer is also formed as it is common among compounds containing S═CR¹—NR²—H group. There is at least 109 such structures deposited in CSD. This motif is particularly common among N-acyl-N'-arylureas and thioureas (Okuniewski et al., 2010). When monosubstituted N-phenylthiourea is considered, chains of molecules can be found (Shen & Xu, 2004). In the title compound an additional N—H···O═C hydrogen bond to acetone is formed stabilizing the structure. Crystals are well formed and grow up to several milimeters in just one day.

There is no π···π stacking in this structure, but some weak C—H···π interactions can be found (see Tab. 1).

Melting point, 154°C, is the same as that for pure N,N'-diphenylthiourea. This is because crystals very quickly loose acetone molecules before melting (even at room temperature) and became colourless powder of pure thiourea derivative.

Related literature top

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 top

1.82 g (8 mmol) of commercially available N,N'-diphenylthiourea was added to 25 ml of acetone and gently heated while stirring. After 5 min nearly full dissolution was observed. The mixture was allowed to cool and then was filtered. The filtrate was left for crystalization at room temperature. After one day well formed, colourless shiny crystals were collected. Yield – 1.86 g (81%).

Structure description top

There is no π···π stacking in this structure, but some weak C—H···π interactions can be found (see Tab. 1).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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).

Figures top

Fig. 1. Structure of [SC(NHPh)₂.OC(CH₃)₂]₂ dimer.

N,N'-Diphenylthiourea acetone monosolvate top

Crystal data top

C₁₃H₁₂N₂S·C₃H₆O	D_x = 1.258 Mg m⁻³
M_r = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	2278 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.1883 pixels mm^-1	θ_max = 27°, θ_min = 2.6°
ω scans	h = −9→21
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −7→12
T_min = 0.777, T_max = 0.819	l = −22→17
7549 measured 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)] = 0.039	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(F_o²) + (0.054P)²] where P = (F_o² + 2F_c²)/3
3245 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₂N₂S·C₃H₆O	V = 3023.4 (2) Å³
M_r = 286.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.1797 (6) Å	µ = 0.21 mm⁻¹
b = 10.0736 (4) Å	T = 150 K
c = 17.4700 (7) Å	0.46 × 0.41 × 0.27 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3245 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	2278 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.819	R_int = 0.025
7549 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.32 e Å⁻³
3245 reflections	Δρ_min = −0.21 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂S·C₃H₆O
M_r	286.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	17.1797 (6), 10.0736 (4), 17.4700 (7)
V (Å³)	3023.4 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.46 × 0.41 × 0.27

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.777, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	7549, 3245, 2278
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.092, 0.94
No. of reflections	3245
No. of parameters	191
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.865 (9)	2.480 (13)	3.3240 (13)	165.3 (13)
N2—H2···O1	0.873 (9)	2.091 (14)	2.8993 (18)	153.6 (16)
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) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

Financial support from the Polish Ministry of Science and Higher Education (project No. N N204 150237) is gratefully acknowledged.

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