N,N-Diethyl-N'-phenyl-acetyl-thio-urea.

The title thio-urea mol-ecule, C(13)H(18)N(2)OS, adopts a folded conformation due to the steric hindrance of the two ethyl groups and the acetyl group. In the crystal structure, the acetyl O atom is not involved in hydrogen bonding, but inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background on the chemistry of thio­urea derivatives, see: Choi et al. (2008 ▶); Jones et al. (2008 ▶); Kushwaha et al. (2008 ▶); Su et al. (2006 ▶). For related structures, see: Su (2005 ▶, 2007 ▶); Xian et al. (2004 ▶); Xian (2008 ▶).

Experimental

Crystal data

C13H18N2OS

M = 250.35

Monoclinic,

a = 11.578 (7) Å

b = 12.804 (8) Å

c = 9.176 (6) Å

β = 103.842 (10)°

V = 1320.8 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 (2) K

0.30 × 0.29 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.933, T max = 0.944

7619 measured reflections

3080 independent reflections

2484 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.05

3080 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: APEX2 and SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536808035290/cv2467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035290/cv2467Isup2.hkl

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

C13H18N2OS	F000 = 536
Mr = 250.35	Dx = 1.259 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 11.578 (7) Å	Cell parameters from 3844 reflections
b = 12.804 (8) Å	θ = 2.4–29.9º
c = 9.176 (6) Å	µ = 0.23 mm−1
β = 103.842 (10)º	T = 296 (2) K
V = 1320.8 (15) Å3	Block, colorless
Z = 4	0.30 × 0.29 × 0.25 mm

Bruker SMART CCD area-detector diffractometer	3080 independent reflections
Radiation source: fine-focus sealed tube	2484 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 296(2) K	θmax = 28.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −15→13
Tmin = 0.934, Tmax = 0.944	k = −16→16
7619 measured reflections	l = −12→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.2848P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3080 reflections	Δρmax = 0.48 e Å−3
156 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.61035 (14)	0.09311 (14)	0.9820 (2)	0.0472 (4)
H1	0.6752	0.0776	1.0607	0.057*
C2	0.53176 (18)	0.17042 (15)	0.9993 (2)	0.0570 (5)
H2	0.5441	0.2071	1.0892	0.068*
C3	0.43555 (19)	0.19328 (17)	0.8842 (3)	0.0663 (6)
H3	0.3821	0.2449	0.8962	0.080*
C4	0.41832 (18)	0.1398 (2)	0.7515 (3)	0.0716 (6)
H4	0.3531	0.1552	0.6733	0.086*
C5	0.49718 (16)	0.06344 (17)	0.7335 (2)	0.0577 (5)
H5	0.4856	0.0280	0.6426	0.069*
C6	0.59380 (13)	0.03890 (13)	0.84970 (19)	0.0406 (4)
C7	0.67692 (14)	−0.04934 (13)	0.8329 (2)	0.0457 (4)
H7A	0.7249	−0.0684	0.9311	0.055*
H7B	0.6303	−0.1099	0.7909	0.055*
C8	0.75749 (14)	−0.01928 (13)	0.73300 (19)	0.0426 (4)
C9	0.95069 (13)	0.06202 (11)	0.73941 (17)	0.0359 (3)
C10	1.02328 (16)	0.14815 (14)	0.5447 (2)	0.0488 (4)
H10A	0.9893	0.1590	0.4384	0.059*
H10B	1.0782	0.0899	0.5550	0.059*
C11	1.0909 (2)	0.24531 (17)	0.6105 (3)	0.0755 (6)
H11A	1.0370	0.3033	0.5999	0.113*
H11B	1.1517	0.2601	0.5583	0.113*
H11C	1.1268	0.2340	0.7149	0.113*
C12	0.81587 (16)	0.18024 (14)	0.5634 (2)	0.0491 (4)
H12A	0.8331	0.2545	0.5695	0.059*
H12B	0.7629	0.1657	0.6284	0.059*
C13	0.75285 (19)	0.15330 (19)	0.4033 (2)	0.0675 (6)
H13A	0.7990	0.1781	0.3363	0.101*
H13B	0.6759	0.1858	0.3788	0.101*
H13C	0.7438	0.0789	0.3935	0.101*
N1	0.85660 (11)	0.03650 (10)	0.80451 (15)	0.0398 (3)
H1'	0.8610	0.0570	0.8949	0.048*
N2	0.92772 (11)	0.12212 (10)	0.61873 (14)	0.0387 (3)
O1	0.73627 (12)	−0.04082 (12)	0.60141 (15)	0.0640 (4)
S1	1.08598 (3)	0.01581 (4)	0.82130 (5)	0.04902 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0353 (8)	0.0537 (9)	0.0528 (10)	−0.0047 (7)	0.0107 (7)	0.0001 (8)
C2	0.0569 (11)	0.0526 (10)	0.0681 (12)	−0.0026 (8)	0.0276 (9)	−0.0033 (9)
C3	0.0603 (12)	0.0608 (11)	0.0887 (16)	0.0197 (10)	0.0394 (11)	0.0248 (11)
C4	0.0507 (11)	0.0962 (16)	0.0667 (13)	0.0215 (11)	0.0120 (10)	0.0285 (12)
C5	0.0466 (10)	0.0793 (13)	0.0460 (10)	0.0026 (9)	0.0088 (8)	0.0047 (9)
C6	0.0312 (7)	0.0456 (8)	0.0473 (9)	−0.0053 (6)	0.0135 (6)	0.0047 (7)
C7	0.0391 (8)	0.0452 (8)	0.0553 (10)	−0.0041 (7)	0.0166 (7)	0.0006 (7)
C8	0.0372 (8)	0.0469 (8)	0.0445 (9)	0.0000 (7)	0.0114 (7)	−0.0029 (7)
C9	0.0347 (7)	0.0387 (7)	0.0351 (7)	−0.0001 (6)	0.0101 (6)	−0.0047 (6)
C10	0.0481 (9)	0.0569 (10)	0.0460 (9)	−0.0014 (8)	0.0203 (7)	0.0064 (8)
C11	0.0678 (13)	0.0557 (11)	0.1072 (19)	−0.0136 (10)	0.0293 (13)	0.0072 (12)
C12	0.0502 (9)	0.0500 (9)	0.0473 (9)	0.0154 (7)	0.0124 (7)	0.0034 (7)
C13	0.0625 (12)	0.0880 (15)	0.0467 (10)	0.0285 (11)	0.0026 (9)	0.0024 (10)
N1	0.0344 (6)	0.0527 (8)	0.0340 (6)	−0.0010 (5)	0.0115 (5)	−0.0037 (6)
N2	0.0375 (7)	0.0411 (7)	0.0386 (7)	0.0032 (5)	0.0115 (5)	−0.0004 (5)
O1	0.0590 (8)	0.0866 (10)	0.0472 (8)	−0.0209 (7)	0.0143 (6)	−0.0180 (7)
S1	0.0346 (2)	0.0687 (3)	0.0442 (3)	0.00839 (18)	0.01022 (17)	0.00658 (19)

C1—C6	1.371 (2)	C9—N1	1.401 (2)
C1—C2	1.379 (3)	C9—S1	1.6747 (17)
C1—H1	0.9300	C10—N2	1.469 (2)
C2—C3	1.371 (3)	C10—C11	1.516 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.370 (4)	C10—H10B	0.9700
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.374 (3)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.384 (2)	C12—N2	1.474 (2)
C5—H5	0.9300	C12—C13	1.515 (3)
C6—C7	1.516 (2)	C12—H12A	0.9700
C7—C8	1.506 (2)	C12—H12B	0.9700
C7—H7A	0.9700	C13—H13A	0.9600
C7—H7B	0.9700	C13—H13B	0.9600
C8—O1	1.205 (2)	C13—H13C	0.9600
C8—N1	1.377 (2)	N1—H1'	0.8600
C9—N2	1.322 (2)
C6—C1—C2	120.61 (17)	N2—C10—C11	112.09 (16)
C6—C1—H1	119.7	N2—C10—H10A	109.2
C2—C1—H1	119.7	C11—C10—H10A	109.2
C3—C2—C1	120.1 (2)	N2—C10—H10B	109.2
C3—C2—H2	120.0	C11—C10—H10B	109.2
C1—C2—H2	120.0	H10A—C10—H10B	107.9
C4—C3—C2	119.81 (19)	C10—C11—H11A	109.5
C4—C3—H3	120.1	C10—C11—H11B	109.5
C2—C3—H3	120.1	H11A—C11—H11B	109.5
C3—C4—C5	120.2 (2)	C10—C11—H11C	109.5
C3—C4—H4	119.9	H11A—C11—H11C	109.5
C5—C4—H4	119.9	H11B—C11—H11C	109.5
C4—C5—C6	120.4 (2)	N2—C12—C13	113.49 (14)
C4—C5—H5	119.8	N2—C12—H12A	108.9
C6—C5—H5	119.8	C13—C12—H12A	108.9
C1—C6—C5	118.89 (17)	N2—C12—H12B	108.9
C1—C6—C7	120.65 (15)	C13—C12—H12B	108.9
C5—C6—C7	120.42 (17)	H12A—C12—H12B	107.7
C8—C7—C6	111.86 (14)	C12—C13—H13A	109.5
C8—C7—H7A	109.2	C12—C13—H13B	109.5
C6—C7—H7A	109.2	H13A—C13—H13B	109.5
C8—C7—H7B	109.2	C12—C13—H13C	109.5
C6—C7—H7B	109.2	H13A—C13—H13C	109.5
H7A—C7—H7B	107.9	H13B—C13—H13C	109.5
O1—C8—N1	122.88 (15)	C8—N1—C9	124.21 (14)
O1—C8—C7	122.95 (16)	C8—N1—H1'	117.9
N1—C8—C7	114.16 (15)	C9—N1—H1'	117.9
N2—C9—N1	118.15 (13)	C9—N2—C10	119.78 (13)
N2—C9—S1	124.09 (12)	C9—N2—C12	124.49 (13)
N1—C9—S1	117.75 (12)	C10—N2—C12	115.02 (14)
C6—C1—C2—C3	0.4 (3)	O1—C8—N1—C9	−8.9 (3)
C1—C2—C3—C4	−0.6 (3)	C7—C8—N1—C9	172.09 (14)
C2—C3—C4—C5	0.0 (3)	N2—C9—N1—C8	62.2 (2)
C3—C4—C5—C6	0.8 (3)	S1—C9—N1—C8	−118.74 (15)
C2—C1—C6—C5	0.4 (2)	N1—C9—N2—C10	−178.25 (14)
C2—C1—C6—C7	−177.23 (15)	S1—C9—N2—C10	2.7 (2)
C4—C5—C6—C1	−1.0 (3)	N1—C9—N2—C12	11.9 (2)
C4—C5—C6—C7	176.60 (17)	S1—C9—N2—C12	−167.16 (12)
C1—C6—C7—C8	−107.78 (18)	C11—C10—N2—C9	−88.3 (2)
C5—C6—C7—C8	74.7 (2)	C11—C10—N2—C12	82.5 (2)
C6—C7—C8—O1	−96.5 (2)	C13—C12—N2—C9	−122.62 (19)
C6—C7—C8—N1	82.50 (18)	C13—C12—N2—C10	67.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1'···S1i	0.86	2.69	3.404 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1′⋯S1i	0.86	2.69	3.404 (3)	141

Symmetry code: (i) .