1-Benzoyl-3-ethyl-3-phenyl­thio­urea

Al-abbasi, A.A.; Kassim, M.B.

doi:10.1107/S1600536811004326

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o611

doi:10.1107/S1600536811004326

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1-Benzoyl-3-ethyl-3-phenylthiourea

Aisha A. Al-abbasi ^a and Mohammad B. Kassim ^a ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 26 January 2011; accepted 4 February 2011; online 12 February 2011)

In the title compound, C₁₆H₁₆N₂OS, the conformation at the two partially double C—N bonds of the thiourea unit is E. The amide group is twisted relative to the thiourea fragment, forming a dihedral angle of 62.44 (16)°, and the two phenyl rings form a dihedral angle 75.93 (18)°. In the crystal, molecules 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_r = 284.37
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.144
S = 1.06
2648 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

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

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

checkCIF report

Comment top

The ethyl group and S-atom are in cis-configuration with respect to the N2—C8 bond, however, the N2-phenyl and benzoyl groups are trans to S-atom with respect to both C—N thiourea bonds (Fig. 1).

The benzene ring [C1/C2/C3/C4/C5/C6/C7] (A), phenyl ring [N2/C9/C10/C11/C12/C13/C14] (B) and the thiourea [(S1/N1/N2/C8/] (C) fragment are essentially planar. The dihedral angle between the plane A and the plane B is 75.93 (15)° whereas, the dihedral angle between thiourea plane (C) and both planes (A, B) are 87.99 (11) and 62.44 (16)°, respectively. Furthermore, the amide group [N2/C9/C10/C11/C12/C13/C14] (D) is twisted relative to the thiourea fragment (C) forming a dihedral angle of 62.44 (16)°.

In addition, the molecules are linked by N1—H···S1 hydrogen bonds (Table 1, Fig. 2) to form centrosymmetric dimers.

Related literature top

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

Experimental top

The reaction scheme involved a reaction of benzoyl chloride (10 mmol) with ammonium thiocyanate (10 mmol) in acetone. The product, benzoyl isothiocyanate was reacted with N-ethylaniline (10 mmol) to give the title compound with 80% yield. A slow evaporation of the reaction mixture give light yellow crystals suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule with displacement ellipsods drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed down the a-axis. Hydrogen bonds are drawn as dashed lines.

1-Benzoyl-3-ethyl-3-phenylthiourea top

Crystal data top

C₁₆H₁₆N₂OS	Z = 2
M_r = 284.37	F(000) = 300
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	2329 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scan	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.908, T_max = 0.961	k = −9→9
7829 measured reflections	l = −14→14

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)] = 0.054	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(F_o²) + (0.0752P)² + 0.3013P] where P = (F_o² + 2F_c²)/3
2648 reflections	(Δ/σ)_max < 0.001
189 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₆N₂OS	γ = 94.205 (6)°
M_r = 284.37	V = 751.3 (4) Å³
Triclinic, P1	Z = 2
a = 7.735 (2) Å	Mo Kα radiation
b = 8.013 (2) Å	µ = 0.21 mm⁻¹
c = 12.540 (3) Å	T = 298 K
α = 101.837 (5)°	0.53 × 0.38 × 0.19 mm
β = 96.908 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2648 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2329 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.961	R_int = 0.023
7829 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.35 e Å⁻³
2648 reflections	Δρ_min = −0.30 e Å⁻³
189 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂OS
M_r	284.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.735 (2), 8.013 (2), 12.540 (3)
α, β, γ (°)	101.837 (5), 96.908 (5), 94.205 (6)
V (Å³)	751.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.53 × 0.38 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.908, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	7829, 2648, 2329
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.144, 1.06
No. of reflections	2648
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing the facilities and grants (UKM-GUP-BTT-07–30–190 & UKMST-06-FRGS0111–2009) and the Libyan Government and Sabha University, Libya, for providing a scholarship for AA.

References

Al-abbasi, A. A., Yarmo, M. A. & Kassim, M. B. (2010). Acta Cryst. E66, o2896. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hung, W. W., Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2010). Acta Cryst. E66, o314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar