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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3414
https://doi.org/10.1107/S1600536811049208

1,1-Di­ethyl-3-(4-meth­­oxy­benzo­yl)thio­urea

Aisha A. Al-abbasi,a Mohamed Ibrahim Mohamed Tahirb and Mohammad B. Kassima,c*

aSchool of Chemical Sciences & Food Technology, Faculty of Science & Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia, bDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia, and cFuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia
*Correspondence e-mail: mbkassim@ukm.my

(Received 17 November 2011; accepted 18 November 2011; online 25 November 2011)

In the title compound, C13H18N2O2S, the 4-meth­oxy­benzoyl fragment is approximately planar [maximum deviation = 0.057 (2) Å] and twisted relative to the thio­amide fragment, forming a dihedral angle of 86.62 (6)°. The two Csp2—Nsp2 bonds in the thio­urea unit differ significantly in length [1.327 (2) and 1.431 (2) Å]. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains parallel to [010].

Related literature

For structural parameters and chemical properties of 1,1 disubstituted 3-benzoyl­thio­ureas, see: Al-abbasi et al. (2010[Al-abbasi, A. A., Yarmo, M. A. & Kassim, M. B. (2010). Acta Cryst. E66, o2896.], 2011[Al-abbasi, A. A., Yamin, B. M. & Kassim, M. B. (2011). Acta Cryst. E67, o1891.]); Al-abbasi & Kassim (2011[Al-abbasi, A. A. & Kassim, M. B. (2011). Acta Cryst. E67, o611.]); Mohamadou et al. (1994[Mohamadou, A., Dechamps-Olivier, I. & Barbier, J. (1994). Polyhedron, 13, 1363-1370.]).

[Scheme 1]

Experimental

Crystal data

  • C13H18N2O2S

  • Mr = 266.35

  • Orthorhombic, P b c a

  • a = 12.9024 (5) Å

  • b = 10.0095 (4) Å

  • c = 20.8585 (11) Å

  • V = 2693.8 (2) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.11 mm−1

  • T = 150 K

  • 0.24 × 0.10 × 0.05 mm
Data collection

  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]) Tmin = 0.810, Tmax = 0.900

  • 12046 measured reflections

  • 2548 independent reflections

  • 2214 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.132

  • S = 1.12

  • 2548 reflections

  • 163 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1i 0.86 2.05 2.847 (2) 154
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049208/gk2435sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049208/gk2435Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049208/gk2435Isup3.cml

checkCIF report


Comment top

The title compound (I) has been used as a ligand to form stable complexes with Ni and Co (Mohamadou et al., 1994). Compund I and other similar derivatives act as a bidentate (O,S) chelate forming square planar and tetrahedral complexes with NiII and CoIII, respectively.

In the structure of I, the 4-methoxybenzamide moiety [O2/N1/C1/C2/C3/C4/C5/C6/C7/C8/C13] (A) and the thiourea fragment [S1/N1/N2/C8] (B) are essentially planar with maximum deviations from the mean planes 0.057 (2) Å for C13 and -0.031 (2) Å N1. The dihedral angle between the A and B planes is 86.62 (6)°, which is slightly smaller than the analogous dihedral angle [87.99 (11)°] in 1-benzoyl-3-ethyl-3-phenylthiourea (II) (Al-abbasi & Kassim, 2011).

The C=O [1.237 (2) Å] and C=S [1.658 (3) Å] bond lengths are slightly longer than those in II [1.207 (3) and 1.666 (2) Å, respectively].

In the crystal, the molecules are stabilized by intermolecular N1—H1A···O1 hydrogen bonds forming a one-dimensional polymeric network along the b axis (Figure 2).

Related literature top

For structural parameters and chemical properties of 1,1 disubstituted 3-benzoylthioureas, see: Al-abbasi et al. (2010, 2011); Al-abbasi & Kassim (2011); Mohamadou et al. (1994).

Experimental top

A solution of benzoyl chloride (10 mmol) in acetone was added slowly to an equimolar solution of ammonium thiocyanate in acetone. The reaction mixture was stirred at room temperature before adding diethylamine (10 mmol) slowly and the mixture was left stirring at room temperature for 2–3 h. The mixture was poured onto a water-ice, filtered and the residue was recrystallized from ethaaol/acetone solution to give colourless crystals, suitable for X-ray crystallography (yield 85%).

Refinement top

The hydrogen atom positions were calculated geometrically and refined in a riding model approximation with C–H bond lengths in the range 0.93–0.97 Å and N-H= 0.86 Å with Uiso(H) = 1.2Ueq(C, N) for N-H, aromatic C-H and CH2 groups, and Uiso(H) = 1.5Ueq(C) for methyl group.

Structure description top

The title compound (I) has been used as a ligand to form stable complexes with Ni and Co (Mohamadou et al., 1994). Compund I and other similar derivatives act as a bidentate (O,S) chelate forming square planar and tetrahedral complexes with NiII and CoIII, respectively.

In the structure of I, the 4-methoxybenzamide moiety [O2/N1/C1/C2/C3/C4/C5/C6/C7/C8/C13] (A) and the thiourea fragment [S1/N1/N2/C8] (B) are essentially planar with maximum deviations from the mean planes 0.057 (2) Å for C13 and -0.031 (2) Å N1. The dihedral angle between the A and B planes is 86.62 (6)°, which is slightly smaller than the analogous dihedral angle [87.99 (11)°] in 1-benzoyl-3-ethyl-3-phenylthiourea (II) (Al-abbasi & Kassim, 2011).

The C=O [1.237 (2) Å] and C=S [1.658 (3) Å] bond lengths are slightly longer than those in II [1.207 (3) and 1.666 (2) Å, respectively].

In the crystal, the molecules are stabilized by intermolecular N1—H1A···O1 hydrogen bonds forming a one-dimensional polymeric network along the b axis (Figure 2).

For structural parameters and chemical properties of 1,1 disubstituted 3-benzoylthioureas, see: Al-abbasi et al. (2010, 2011); Al-abbasi & Kassim (2011); Mohamadou et al. (1994).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of 1,1-diethyl-3-(4-methoxybenzoyl)thiourea with displacement ellipsods drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of 1,1-diethyl-3-(4-methoxybenzoyl)thiourea with intermolecular hydrogen bonds shown as dashed lines.
1,1-Diethyl-3-(4-methoxybenzoyl)thiourea top
Crystal data top
C13H18N2O2SDx = 1.314 Mg m−3
Mr = 266.35Melting point = 407.15–408.15 K
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 5648 reflections
a = 12.9024 (5) Åθ = 4.2–71.1°
b = 10.0095 (4) ŵ = 2.11 mm−1
c = 20.8585 (11) ÅT = 150 K
V = 2693.8 (2) Å3Plate, colourless
Z = 80.24 × 0.10 × 0.05 mm
F(000) = 1136
Data collection top
Oxford Diffraction Gemini
diffractometer		2548 independent reflections
Radiation source: fine-focus sealed tube2214 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω/2θ scansθmax = 71.1°, θmin = 4.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		h = −13→15
Tmin = 0.810, Tmax = 0.900k = −12→12
12046 measured reflectionsl = −23→25
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0835P)2 + 0.6035P]
where P = (Fo2 + 2Fc2)/3
2548 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C13H18N2O2SV = 2693.8 (2) Å3
Mr = 266.35Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 12.9024 (5) ŵ = 2.11 mm−1
b = 10.0095 (4) ÅT = 150 K
c = 20.8585 (11) Å0.24 × 0.10 × 0.05 mm
Data collection top
Oxford Diffraction Gemini
diffractometer		2548 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		2214 reflections with I > 2σ(I)
Tmin = 0.810, Tmax = 0.900Rint = 0.030
12046 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.12Δρmax = 0.43 e Å−3
2548 reflectionsΔρmin = −0.32 e Å−3
163 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.

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
xyzUiso*/Ueq
S10.96773 (4)0.08865 (5)0.60731 (2)0.0302 (2)
O10.72174 (10)0.27396 (13)0.63046 (7)0.0282 (3)
O20.29590 (10)0.00839 (15)0.54492 (7)0.0327 (4)
N10.76759 (11)0.05775 (15)0.63691 (7)0.0210 (3)
H1A0.7495−0.02460.63320.025*
N20.87609 (11)0.11414 (15)0.72156 (7)0.0215 (3)
C10.52575 (14)0.21406 (19)0.58056 (9)0.0242 (4)
H1B0.54720.30280.58110.029*
C20.42448 (15)0.1834 (2)0.56253 (9)0.0271 (4)
H2A0.37850.25100.55130.033*
C30.39293 (14)0.0509 (2)0.56149 (8)0.0246 (4)
C40.46228 (14)−0.05050 (19)0.57806 (9)0.0236 (4)
H4A0.4410−0.13930.57710.028*
C50.56228 (14)−0.01898 (19)0.59584 (8)0.0220 (4)
H5A0.6082−0.08700.60670.026*
C60.59545 (14)0.11370 (18)0.59775 (8)0.0201 (4)
C70.69945 (13)0.15522 (17)0.62164 (8)0.0202 (4)
C80.86948 (13)0.08980 (16)0.65915 (9)0.0213 (4)
C90.78567 (13)0.11498 (19)0.76513 (9)0.0236 (4)
H9A0.72650.15240.74270.028*
H9B0.80070.17210.80150.028*
C100.75793 (15)−0.0231 (2)0.78918 (10)0.0298 (4)
H10A0.6989−0.01740.81710.045*
H10B0.8156−0.05990.81230.045*
H10C0.7417−0.07980.75340.045*
C110.97664 (13)0.14064 (18)0.75210 (9)0.0246 (4)
H11A1.03100.09730.72770.029*
H11B0.97680.10280.79490.029*
C120.99913 (15)0.28917 (19)0.75623 (10)0.0296 (5)
H12A1.06500.30280.77660.044*
H12B0.94590.33220.78080.044*
H12C1.00080.32650.71380.044*
C130.22137 (16)0.1077 (3)0.52797 (11)0.0401 (5)
H13A0.15670.06540.51770.060*
H13B0.24570.15690.49140.060*
H13C0.21160.16760.56340.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0251 (3)0.0307 (3)0.0347 (3)−0.00535 (18)0.00843 (18)−0.00309 (18)
O10.0258 (7)0.0211 (7)0.0378 (8)−0.0015 (5)−0.0037 (6)0.0012 (5)
O20.0193 (7)0.0438 (9)0.0351 (8)−0.0006 (6)−0.0042 (5)0.0002 (6)
N10.0196 (7)0.0170 (8)0.0265 (8)−0.0021 (5)−0.0025 (6)−0.0007 (6)
N20.0188 (7)0.0181 (7)0.0275 (8)−0.0002 (5)−0.0016 (6)0.0003 (6)
C10.0273 (10)0.0215 (10)0.0238 (10)0.0017 (7)0.0004 (7)0.0011 (7)
C20.0255 (9)0.0315 (11)0.0244 (9)0.0085 (8)−0.0015 (7)0.0035 (7)
C30.0207 (9)0.0348 (11)0.0184 (9)0.0003 (7)0.0004 (6)−0.0014 (7)
C40.0242 (9)0.0227 (9)0.0239 (10)−0.0025 (7)0.0016 (7)−0.0026 (7)
C50.0209 (9)0.0240 (9)0.0212 (9)0.0018 (7)0.0021 (6)0.0005 (7)
C60.0210 (9)0.0206 (9)0.0187 (8)0.0009 (7)0.0016 (6)−0.0006 (6)
C70.0226 (9)0.0184 (9)0.0197 (8)−0.0012 (7)0.0022 (6)0.0008 (6)
C80.0194 (9)0.0149 (9)0.0295 (10)0.0000 (6)−0.0012 (7)0.0010 (6)
C90.0220 (9)0.0222 (9)0.0265 (10)0.0007 (7)0.0001 (7)−0.0027 (7)
C100.0261 (10)0.0314 (11)0.0318 (10)−0.0026 (8)0.0028 (8)0.0030 (8)
C110.0204 (9)0.0211 (10)0.0323 (10)0.0008 (7)−0.0066 (7)0.0002 (7)
C120.0252 (9)0.0268 (11)0.0367 (11)−0.0050 (7)−0.0082 (8)0.0024 (8)
C130.0229 (10)0.0591 (15)0.0384 (12)0.0080 (9)−0.0058 (8)0.0033 (10)
Geometric parameters (Å, º) top
S1—C81.6663 (18)C5—C61.396 (3)
O1—C71.237 (2)C5—H5A0.9300
O2—C31.367 (2)C6—C71.490 (2)
O2—C131.428 (3)C9—C101.514 (3)
N1—C71.351 (2)C9—H9A0.9700
N1—C81.431 (2)C9—H9B0.9700
N1—H1A0.8600C10—H10A0.9600
N2—C81.327 (2)C10—H10B0.9600
N2—C111.470 (2)C10—H10C0.9600
N2—C91.479 (2)C11—C121.517 (3)
C1—C21.394 (3)C11—H11A0.9700
C1—C61.395 (3)C11—H11B0.9700
C1—H1B0.9300C12—H12A0.9600
C2—C31.387 (3)C12—H12B0.9600
C2—H2A0.9300C12—H12C0.9600
C3—C41.397 (3)C13—H13A0.9600
C4—C51.379 (3)C13—H13B0.9600
C4—H4A0.9300C13—H13C0.9600
C3—O2—C13117.56 (17)N2—C9—C10112.64 (15)
C7—N1—C8120.83 (15)N2—C9—H9A109.1
C7—N1—H1A119.6C10—C9—H9A109.1
C8—N1—H1A119.6N2—C9—H9B109.1
C8—N2—C11121.01 (15)C10—C9—H9B109.1
C8—N2—C9123.58 (14)H9A—C9—H9B107.8
C11—N2—C9115.40 (14)C9—C10—H10A109.5
C2—C1—C6121.00 (17)C9—C10—H10B109.5
C2—C1—H1B119.5H10A—C10—H10B109.5
C6—C1—H1B119.5C9—C10—H10C109.5
C3—C2—C1119.34 (17)H10A—C10—H10C109.5
C3—C2—H2A120.3H10B—C10—H10C109.5
C1—C2—H2A120.3N2—C11—C12111.73 (14)
O2—C3—C2124.80 (17)N2—C11—H11A109.3
O2—C3—C4115.01 (17)C12—C11—H11A109.3
C2—C3—C4120.19 (17)N2—C11—H11B109.3
C5—C4—C3119.97 (18)C12—C11—H11B109.3
C5—C4—H4A120.0H11A—C11—H11B107.9
C3—C4—H4A120.0C11—C12—H12A109.5
C4—C5—C6120.81 (17)C11—C12—H12B109.5
C4—C5—H5A119.6H12A—C12—H12B109.5
C6—C5—H5A119.6C11—C12—H12C109.5
C1—C6—C5118.69 (17)H12A—C12—H12C109.5
C1—C6—C7117.74 (16)H12B—C12—H12C109.5
C5—C6—C7123.43 (16)O2—C13—H13A109.5
O1—C7—N1120.50 (16)O2—C13—H13B109.5
O1—C7—C6121.81 (16)H13A—C13—H13B109.5
N1—C7—C6117.60 (15)O2—C13—H13C109.5
N2—C8—N1114.73 (15)H13A—C13—H13C109.5
N2—C8—S1126.08 (14)H13B—C13—H13C109.5
N1—C8—S1119.16 (13)
C6—C1—C2—C3−0.2 (3)C1—C6—C7—O15.0 (3)
C13—O2—C3—C2−0.6 (3)C5—C6—C7—O1−170.57 (16)
C13—O2—C3—C4179.54 (17)C1—C6—C7—N1−178.57 (16)
C1—C2—C3—O2179.78 (17)C5—C6—C7—N15.9 (2)
C1—C2—C3—C4−0.3 (3)C11—N2—C8—N1176.34 (14)
O2—C3—C4—C5−179.75 (16)C9—N2—C8—N1−2.8 (2)
C2—C3—C4—C50.3 (3)C11—N2—C8—S1−1.5 (2)
C3—C4—C5—C60.2 (3)C9—N2—C8—S1179.41 (13)
C2—C1—C6—C50.8 (3)C7—N1—C8—N284.6 (2)
C2—C1—C6—C7−175.01 (16)C7—N1—C8—S1−97.46 (17)
C4—C5—C6—C1−0.8 (3)C8—N2—C9—C1084.7 (2)
C4—C5—C6—C7174.78 (16)C11—N2—C9—C10−94.45 (18)
C8—N1—C7—O1−4.6 (3)C8—N2—C11—C1294.1 (2)
C8—N1—C7—C6178.96 (15)C9—N2—C11—C12−86.69 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.052.847 (2)154
Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC13H18N2O2S
Mr266.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)12.9024 (5), 10.0095 (4), 20.8585 (11)
V (Å3)2693.8 (2)
Z8
Radiation typeCu Kα
µ (mm−1)2.11
Crystal size (mm)0.24 × 0.10 × 0.05
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2006)
Tmin, Tmax0.810, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections		12046, 2548, 2214
Rint0.030
(sin θ/λ)max (Å−1)0.614
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.132, 1.12
No. of reflections2548
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.43, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.052.847 (2)154
Symmetry code: (i) −x+3/2, y−1/2, z.
 

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (UKM-ST-06-FRGS0111-2009 and UKM-PTS-016-2010) and the Libyan Government for providing a scholarship for AA.

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3414
https://doi.org/10.1107/S1600536811049208
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