1-Benzoyl-3-ethyl-3-phenyl-thio-urea.

In the title compound, C(16)H(16)N(2)OS, the conformation at the two partially double C-N bonds of the thio-urea unit is E. The amide group is twisted relative to the thio-urea fragment, forming a dihedral angle of 62.44 (16)°, and the two phenyl rings form a dihedral angle 75.93 (18)°. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related structures and background references, see: Al-abbasi et al. (2010 ▶); Hung et al. (2010 ▶).

Experimental

Crystal data

C16H16N2OS

M = 284.37

Triclinic,

a = 7.735 (2) Å

b = 8.013 (2) Å

c = 12.540 (3) Å

α = 101.837 (5)°

β = 96.908 (5)°

γ = 94.205 (6)°

V = 751.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.53 × 0.38 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.908, T max = 0.961

7829 measured reflections

2648 independent reflections

2329 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.144

S = 1.06

2648 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004326/gk2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004326/gk2345Isup2.hkl

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

C16H16N2OS	Z = 2
Mr = 284.37	F(000) = 300
Triclinic, P1	Dx = 1.257 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.735 (2) Å	Cell parameters from 4273 reflections
b = 8.013 (2) Å	θ = 1.7–25.0°
c = 12.540 (3) Å	µ = 0.21 mm−1
α = 101.837 (5)°	T = 298 K
β = 96.908 (5)°	Blok, colorless
γ = 94.205 (6)°	0.53 × 0.38 × 0.19 mm
V = 751.3 (4) Å3

Bruker SMART APEX CCD area-detector diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	2329 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scan	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.908, Tmax = 0.961	k = −9→9
7829 measured reflections	l = −14→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0752P)2 + 0.3013P] where P = (Fo2 + 2Fc2)/3
2648 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.30 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	0.23483 (8)	1.04861 (8)	0.44047 (5)	0.0590 (2)
O1	0.2723 (2)	0.5506 (2)	0.26763 (17)	0.0716 (5)
N1	0.4237 (2)	0.8089 (2)	0.34962 (15)	0.0467 (4)
N2	0.2081 (3)	0.8877 (3)	0.23101 (16)	0.0663 (6)
C1	0.5519 (4)	0.3888 (3)	0.3646 (2)	0.0629 (6)
H1B	0.4418	0.3356	0.3670	0.076*
C2	0.6996 (6)	0.3080 (4)	0.3850 (2)	0.0855 (10)
H2A	0.6892	0.2010	0.4029	0.103*
C3	0.8618 (5)	0.3839 (5)	0.3793 (2)	0.0900 (11)
H3A	0.9606	0.3276	0.3922	0.108*
C4	0.8789 (4)	0.5418 (5)	0.3545 (2)	0.0821 (9)
H4A	0.9892	0.5925	0.3502	0.099*
C5	0.7326 (3)	0.6268 (3)	0.33594 (19)	0.0567 (6)
H5A	0.7447	0.7354	0.3204	0.068*
C6	0.5686 (3)	0.5503 (3)	0.34046 (16)	0.0453 (5)
C7	0.4073 (3)	0.6313 (3)	0.31503 (18)	0.0475 (5)
C8	0.2875 (3)	0.9101 (3)	0.33425 (18)	0.0497 (5)
C9	0.2909 (5)	0.8135 (4)	0.1373 (2)	0.0757 (9)
C10	0.4569 (5)	0.8773 (4)	0.1275 (2)	0.0858 (9)
H10A	0.5164	0.9661	0.1822	0.103*
C11	0.5366 (7)	0.8103 (6)	0.0365 (3)	0.1170 (15)
H11A	0.6502	0.8520	0.0317	0.140*
C12	0.4498 (11)	0.6856 (8)	−0.0443 (4)	0.146 (2)
H12A	0.5042	0.6398	−0.1044	0.175*
C13	0.2835 (10)	0.6260 (7)	−0.0388 (3)	0.146 (2)
H13A	0.2219	0.5451	−0.0975	0.175*
C14	0.2019 (7)	0.6853 (6)	0.0554 (3)	0.1116 (15)
H14A	0.092 (4)	0.660 (4)	0.063 (2)	0.067 (10)*
C15	0.0405 (4)	0.9631 (4)	0.2081 (3)	0.0865 (9)
H15A	−0.0407	0.8796	0.1550	0.104*
H15B	−0.0115	0.9914	0.2754	0.104*
C16	0.0708 (5)	1.1179 (5)	0.1650 (3)	0.1049 (11)
H16A	−0.0382	1.1650	0.1512	0.157*
H16B	0.1200	1.0893	0.0976	0.157*
H16C	0.1506	1.2009	0.2178	0.157*
H1A	0.499 (3)	0.850 (3)	0.403 (2)	0.050 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0635 (4)	0.0613 (4)	0.0516 (4)	0.0281 (3)	0.0083 (3)	0.0032 (3)
O1	0.0501 (9)	0.0559 (10)	0.1014 (14)	0.0015 (8)	0.0001 (9)	0.0070 (9)
N1	0.0474 (10)	0.0455 (10)	0.0438 (10)	0.0136 (8)	−0.0009 (8)	0.0026 (8)
N2	0.0700 (13)	0.0692 (13)	0.0521 (11)	0.0319 (10)	−0.0102 (9)	−0.0027 (9)
C1	0.0841 (17)	0.0513 (13)	0.0569 (14)	0.0164 (12)	0.0139 (12)	0.0139 (11)
C2	0.134 (3)	0.0642 (17)	0.0625 (17)	0.0491 (19)	0.0039 (17)	0.0151 (13)
C3	0.099 (2)	0.097 (2)	0.0681 (18)	0.062 (2)	−0.0074 (16)	−0.0040 (16)
C4	0.0544 (15)	0.103 (2)	0.0796 (19)	0.0283 (15)	0.0084 (13)	−0.0085 (17)
C5	0.0528 (13)	0.0592 (13)	0.0578 (13)	0.0148 (10)	0.0140 (10)	0.0049 (11)
C6	0.0545 (12)	0.0439 (11)	0.0376 (10)	0.0146 (9)	0.0101 (8)	0.0036 (8)
C7	0.0476 (12)	0.0452 (11)	0.0505 (12)	0.0088 (9)	0.0110 (9)	0.0086 (9)
C8	0.0499 (11)	0.0465 (11)	0.0509 (12)	0.0119 (9)	0.0031 (9)	0.0061 (9)
C9	0.109 (2)	0.0675 (16)	0.0456 (13)	0.0460 (16)	−0.0089 (14)	0.0000 (12)
C10	0.130 (3)	0.0819 (19)	0.0523 (15)	0.043 (2)	0.0186 (16)	0.0165 (14)
C11	0.183 (4)	0.120 (3)	0.070 (2)	0.074 (3)	0.049 (2)	0.033 (2)
C12	0.262 (7)	0.135 (4)	0.056 (2)	0.116 (5)	0.027 (4)	0.020 (3)
C13	0.245 (6)	0.110 (3)	0.060 (2)	0.085 (4)	−0.032 (3)	−0.029 (2)
C14	0.139 (4)	0.103 (3)	0.071 (2)	0.045 (3)	−0.023 (2)	−0.0209 (19)
C15	0.089 (2)	0.084 (2)	0.0754 (18)	0.0332 (16)	−0.0183 (15)	0.0005 (15)
C16	0.119 (3)	0.104 (3)	0.096 (2)	0.046 (2)	0.007 (2)	0.024 (2)

S1—C8	1.662 (2)	C6—C7	1.479 (3)
O1—C7	1.207 (3)	C9—C14	1.370 (5)
N1—C7	1.392 (3)	C9—C10	1.375 (5)
N1—C8	1.394 (3)	C10—C11	1.392 (4)
N1—H1A	0.83 (2)	C10—H10A	0.9300
N2—C8	1.335 (3)	C11—C12	1.341 (7)
N2—C9	1.448 (3)	C11—H11A	0.9300
N2—C15	1.491 (3)	C12—C13	1.354 (8)
C1—C2	1.377 (4)	C12—H12A	0.9300
C1—C6	1.389 (3)	C13—C14	1.418 (7)
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.370 (5)	C14—H14A	0.88 (3)
C2—H2A	0.9300	C15—C16	1.467 (5)
C3—C4	1.364 (5)	C15—H15A	0.9700
C3—H3A	0.9300	C15—H15B	0.9700
C4—C5	1.383 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.380 (3)	C16—H16C	0.9600
C5—H5A	0.9300
C7—N1—C8	123.84 (19)	C14—C9—C10	119.6 (4)
C7—N1—H1A	116.1 (17)	C14—C9—N2	120.4 (4)
C8—N1—H1A	114.8 (16)	C10—C9—N2	120.0 (3)
C8—N2—C9	122.1 (2)	C9—C10—C11	120.7 (4)
C8—N2—C15	120.0 (2)	C9—C10—H10A	119.7
C9—N2—C15	117.2 (2)	C11—C10—H10A	119.7
C2—C1—C6	119.4 (3)	C12—C11—C10	120.0 (5)
C2—C1—H1B	120.3	C12—C11—H11A	120.0
C6—C1—H1B	120.3	C10—C11—H11A	120.0
C3—C2—C1	120.6 (3)	C11—C12—C13	120.3 (5)
C3—C2—H2A	119.7	C11—C12—H12A	119.8
C1—C2—H2A	119.7	C13—C12—H12A	119.8
C4—C3—C2	120.2 (3)	C12—C13—C14	120.9 (5)
C4—C3—H3A	119.9	C12—C13—H13A	119.5
C2—C3—H3A	119.9	C14—C13—H13A	119.5
C3—C4—C5	120.2 (3)	C9—C14—C13	118.3 (6)
C3—C4—H4A	119.9	C9—C14—H14A	115 (2)
C5—C4—H4A	119.9	C13—C14—H14A	126 (2)
C6—C5—C4	119.9 (3)	C16—C15—N2	110.7 (3)
C6—C5—H5A	120.0	C16—C15—H15A	109.5
C4—C5—H5A	120.0	N2—C15—H15A	109.5
C5—C6—C1	119.7 (2)	C16—C15—H15B	109.5
C5—C6—C7	122.05 (19)	N2—C15—H15B	109.5
C1—C6—C7	118.2 (2)	H15A—C15—H15B	108.1
O1—C7—N1	122.5 (2)	C15—C16—H16A	109.5
O1—C7—C6	122.96 (19)	C15—C16—H16B	109.5
N1—C7—C6	114.58 (18)	H16A—C16—H16B	109.5
N2—C8—N1	115.58 (19)	C15—C16—H16C	109.5
N2—C8—S1	124.27 (16)	H16A—C16—H16C	109.5
N1—C8—S1	120.15 (16)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−1.5 (4)	C15—N2—C8—S1	−12.3 (4)
C1—C2—C3—C4	0.8 (4)	C7—N1—C8—N2	−53.4 (3)
C2—C3—C4—C5	0.5 (4)	C7—N1—C8—S1	127.2 (2)
C3—C4—C5—C6	−1.2 (4)	C8—N2—C9—C14	132.1 (3)
C4—C5—C6—C1	0.5 (3)	C15—N2—C9—C14	−57.0 (4)
C4—C5—C6—C7	−176.4 (2)	C8—N2—C9—C10	−51.0 (4)
C2—C1—C6—C5	0.8 (3)	C15—N2—C9—C10	120.0 (3)
C2—C1—C6—C7	177.9 (2)	C14—C9—C10—C11	−1.4 (5)
C8—N1—C7—O1	0.6 (3)	N2—C9—C10—C11	−178.4 (3)
C8—N1—C7—C6	−179.73 (19)	C9—C10—C11—C12	1.9 (5)
C5—C6—C7—O1	143.2 (2)	C10—C11—C12—C13	1.0 (7)
C1—C6—C7—O1	−33.8 (3)	C11—C12—C13—C14	−4.3 (8)
C5—C6—C7—N1	−36.4 (3)	C10—C9—C14—C13	−1.8 (5)
C1—C6—C7—N1	146.6 (2)	N2—C9—C14—C13	175.2 (3)
C9—N2—C8—N1	−21.0 (4)	C12—C13—C14—C9	4.7 (7)
C15—N2—C8—N1	168.3 (2)	C8—N2—C15—C16	102.9 (3)
C9—N2—C8—S1	158.4 (2)	C9—N2—C15—C16	−68.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.83 (2)	2.62 (2)	3.444 (2)	172 (2)
C4—H4A···O1ii	0.93	2.55	3.354 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.83 (2)	2.62 (2)	3.444 (2)	172 (2)

Symmetry code: (i) .