organic compounds
3-Acetyl-1-(2,3-dimethylphenyl)thiourea
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
In the 11H14N2OS, the conformation of the two N—H bonds is anti. The conformation of the C=S and the C=O bonds is also anti. Furthermore, the N—H bond adjacent to the benzene ring is anti to the ortho- and meta-methyl groups. The dihedral angle between the benzene ring and the side chain [N—C(= S)—N—C(=O)—C; maximum deviation = 0.047 (4) Å] is 81.33 (10)°. The NH hydrogen adjacent to the benzene ring and the amide O atom exhibit bifurcated intra- and intermolecular hydrogen bonding. In the crystal, molecules form inversion dimers, which are linked into chains via R22(12) and R22(8) networks.
of the title compound, CRelated literature
For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2006); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Jyothi & Gowda (2004); Shetty & Gowda (2004).
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812027973/nc2285sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027973/nc2285Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812027973/nc2285Isup3.cml
3-Acetyl-1-(2,3-dimethylphenyl)thiourea was synthesized by adding a solution of acetyl chloride (0.10 mol) in acetone (30 ml) dropwise to a suspension of ammonium thiocyanate (0.10 mol) in acetone (30 ml). The reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 2,3-dimethylaniline (0.10 mol) in acetone (10 ml) was added and refluxed for 3 h. The reaction mixture was poured into acidified cold water. The precipitated title compound was recrystallized to constant melting point from acetonitrile. The purity of the compound was checked and characterized by its infrared spectrum.
Needle like colourless single crystals used in X-ray diffraction studies were grown in acetonitrile solution by slow evaporation of the solvent at room temperature.
All C—H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined isotropic with Uiso(H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.93 Å for aromatic and C—H = 0.96 Å for methyl H atoms. The amino H atoms were refined with the N—H distances restrained to 0.86 (2) Å.
Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They are known to exhibit a wide variety of biological activities. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Jyothi & Gowda, 2004; Shetty & Gowda, 2004), in the present work, the
of 3-acetyl-1-(2,3-dimethylphenyl)thiourea has been determined (Fig. 1).The conformation of the two N—H bonds are anti to each other, and one of them is anti to the C═S in the urea segment and the other orients away from it. The adjacent N—H bond is anti to the ortho- and meta-methyl groups in the benzene ring. Furthermore, the conformations of the amide C═S and the C═O are anti to each other, similar to the anti conformation observed in 3-acetyl-1-(2-methylphenyl)thiourea (Shahwar et al., 2012).
The side chain is oriented itself with respect to the phenyl ring with the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = - 99.89 (44)°. The dihedral angle between the phenyl ring and the side chain is 81.33 (10)°.
The hydrogen atom of the NH attached to the phenyl ring and the amide oxygen exhibit a bifurcated hydrogen bonding by showing the simultaneous intra and intermolecular hydrogen bonding. In the crystal, the molecules form inversion type dimers which are linked into infinite chains in terms of R22(12) and R22(8) networks through series of N—H···O and N—H···S intermolecular hydrogen bonds, respectively (Table 1, Fig.2).
For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2006); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Jyothi & Gowda (2004); Shetty & Gowda (2004).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C11H14N2OS | Z = 2 |
Mr = 222.30 | F(000) = 236 |
Triclinic, P1 | Dx = 1.290 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0552 (7) Å | Cell parameters from 1147 reflections |
b = 9.869 (2) Å | θ = 3.5–27.8° |
c = 12.028 (3) Å | µ = 0.26 mm−1 |
α = 106.71 (1)° | T = 293 K |
β = 91.01 (1)° | Needle, colourless |
γ = 94.57 (1)° | 0.48 × 0.08 × 0.04 mm |
V = 572.4 (2) Å3 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2066 independent reflections |
Radiation source: fine-focus sealed tube | 1331 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Rotation method data acquisition using ω and phi scans | θmax = 25.3°, θmin = 3.5° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −6→6 |
Tmin = 0.886, Tmax = 0.990 | k = −11→11 |
3414 measured reflections | l = −13→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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0493P)2 + 0.4018P] where P = (Fo2 + 2Fc2)/3 |
2066 reflections | (Δ/σ)max = 0.003 |
145 parameters | Δρmax = 0.33 e Å−3 |
5 restraints | Δρmin = −0.24 e Å−3 |
C11H14N2OS | γ = 94.57 (1)° |
Mr = 222.30 | V = 572.4 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.0552 (7) Å | Mo Kα radiation |
b = 9.869 (2) Å | µ = 0.26 mm−1 |
c = 12.028 (3) Å | T = 293 K |
α = 106.71 (1)° | 0.48 × 0.08 × 0.04 mm |
β = 91.01 (1)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2066 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 1331 reflections with I > 2σ(I) |
Tmin = 0.886, Tmax = 0.990 | Rint = 0.028 |
3414 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 5 restraints |
wR(F2) = 0.141 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.33 e Å−3 |
2066 reflections | Δρmin = −0.24 e Å−3 |
145 parameters |
Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | 1.1098 (2) | 0.43318 (11) | 0.14467 (9) | 0.0458 (3) | |
O1 | 0.4254 (5) | 0.1213 (3) | −0.0465 (2) | 0.0552 (8) | |
N1 | 0.7872 (6) | 0.2041 (3) | 0.1289 (3) | 0.0432 (8) | |
H1N | 0.674 (6) | 0.140 (3) | 0.086 (3) | 0.052* | |
N2 | 0.7252 (6) | 0.3141 (3) | −0.0129 (3) | 0.0382 (7) | |
H2N | 0.773 (7) | 0.378 (3) | −0.043 (3) | 0.046* | |
C1 | 0.9070 (7) | 0.1817 (4) | 0.2310 (3) | 0.0438 (10) | |
C2 | 0.8249 (7) | 0.2551 (4) | 0.3383 (3) | 0.0477 (10) | |
C3 | 0.9350 (9) | 0.2228 (5) | 0.4369 (4) | 0.0584 (10) | |
C4 | 1.1149 (9) | 0.1232 (5) | 0.4189 (4) | 0.0658 (11) | |
H4 | 1.1871 | 0.1023 | 0.4831 | 0.079* | |
C5 | 1.1947 (10) | 0.0521 (5) | 0.3101 (4) | 0.0717 (12) | |
H5 | 1.3189 | −0.0143 | 0.3020 | 0.086* | |
C6 | 1.0896 (8) | 0.0800 (4) | 0.2137 (4) | 0.0538 (11) | |
H6 | 1.1389 | 0.0326 | 0.1394 | 0.065* | |
C7 | 0.8621 (7) | 0.3091 (4) | 0.0861 (3) | 0.0356 (8) | |
C8 | 0.5121 (7) | 0.2265 (4) | −0.0728 (3) | 0.0384 (9) | |
C9 | 0.3956 (8) | 0.2699 (4) | −0.1700 (3) | 0.0509 (10) | |
H9A | 0.5356 | 0.2990 | −0.2134 | 0.076* | |
H9B | 0.2895 | 0.3476 | −0.1395 | 0.076* | |
H9C | 0.2864 | 0.1913 | −0.2201 | 0.076* | |
C10 | 0.6334 (8) | 0.3630 (5) | 0.3534 (4) | 0.0613 (12) | |
H10A | 0.5392 | 0.3513 | 0.2808 | 0.092* | |
H10B | 0.7265 | 0.4560 | 0.3788 | 0.092* | |
H10C | 0.5097 | 0.3522 | 0.4105 | 0.092* | |
C11 | 0.8541 (11) | 0.2953 (6) | 0.5555 (4) | 0.0948 (18) | |
H11A | 0.6719 | 0.2654 | 0.5637 | 0.142* | |
H11B | 0.8734 | 0.3962 | 0.5680 | 0.142* | |
H11C | 0.9643 | 0.2713 | 0.6116 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0475 (6) | 0.0432 (6) | 0.0496 (6) | −0.0111 (4) | −0.0123 (4) | 0.0231 (5) |
O1 | 0.0659 (18) | 0.0452 (16) | 0.0549 (17) | −0.0173 (14) | −0.0174 (14) | 0.0224 (14) |
N1 | 0.050 (2) | 0.0423 (19) | 0.0379 (18) | −0.0132 (15) | −0.0127 (15) | 0.0177 (15) |
N2 | 0.0417 (18) | 0.0414 (19) | 0.0363 (17) | −0.0026 (15) | −0.0002 (14) | 0.0210 (14) |
C1 | 0.048 (2) | 0.043 (2) | 0.044 (2) | −0.0116 (19) | −0.0029 (18) | 0.0217 (19) |
C2 | 0.038 (2) | 0.051 (3) | 0.055 (3) | −0.0107 (19) | 0.0014 (19) | 0.021 (2) |
C3 | 0.061 (3) | 0.071 (3) | 0.045 (2) | −0.0172 (17) | −0.0050 (19) | 0.025 (2) |
C4 | 0.071 (3) | 0.072 (3) | 0.064 (2) | −0.0141 (18) | −0.018 (2) | 0.041 (2) |
C5 | 0.079 (3) | 0.061 (3) | 0.084 (3) | 0.009 (2) | −0.007 (3) | 0.035 (2) |
C6 | 0.057 (3) | 0.050 (3) | 0.063 (3) | 0.001 (2) | −0.005 (2) | 0.030 (2) |
C7 | 0.040 (2) | 0.035 (2) | 0.034 (2) | 0.0021 (16) | 0.0001 (16) | 0.0136 (17) |
C8 | 0.041 (2) | 0.038 (2) | 0.036 (2) | 0.0006 (18) | 0.0001 (17) | 0.0097 (17) |
C9 | 0.053 (2) | 0.055 (3) | 0.047 (2) | −0.001 (2) | −0.0118 (19) | 0.020 (2) |
C10 | 0.060 (3) | 0.068 (3) | 0.052 (3) | 0.002 (2) | 0.010 (2) | 0.012 (2) |
C11 | 0.108 (4) | 0.120 (5) | 0.053 (3) | −0.017 (4) | −0.006 (3) | 0.029 (3) |
S1—C7 | 1.671 (4) | C4—H4 | 0.9300 |
O1—C8 | 1.221 (4) | C5—C6 | 1.374 (6) |
N1—C7 | 1.316 (4) | C5—H5 | 0.9300 |
N1—C1 | 1.440 (4) | C6—H6 | 0.9300 |
N1—H1N | 0.856 (18) | C8—C9 | 1.484 (5) |
N2—C8 | 1.375 (4) | C9—H9A | 0.9600 |
N2—C7 | 1.383 (4) | C9—H9B | 0.9600 |
N2—H2N | 0.838 (18) | C9—H9C | 0.9600 |
C1—C2 | 1.376 (5) | C10—H10A | 0.9600 |
C1—C6 | 1.391 (5) | C10—H10B | 0.9600 |
C2—C3 | 1.429 (5) | C10—H10C | 0.9600 |
C2—C10 | 1.470 (5) | C11—H11A | 0.9600 |
C3—C4 | 1.366 (6) | C11—H11B | 0.9600 |
C3—C11 | 1.481 (6) | C11—H11C | 0.9600 |
C4—C5 | 1.380 (7) | ||
C7—N1—C1 | 124.6 (3) | N1—C7—N2 | 116.9 (3) |
C7—N1—H1N | 115 (3) | N1—C7—S1 | 123.6 (3) |
C1—N1—H1N | 120 (3) | N2—C7—S1 | 119.5 (3) |
C8—N2—C7 | 129.1 (3) | O1—C8—N2 | 121.9 (3) |
C8—N2—H2N | 113 (3) | O1—C8—C9 | 122.9 (3) |
C7—N2—H2N | 118 (3) | N2—C8—C9 | 115.2 (3) |
C2—C1—C6 | 124.1 (4) | C8—C9—H9A | 109.5 |
C2—C1—N1 | 118.7 (4) | C8—C9—H9B | 109.5 |
C6—C1—N1 | 117.1 (4) | H9A—C9—H9B | 109.5 |
C1—C2—C3 | 117.0 (4) | C8—C9—H9C | 109.5 |
C1—C2—C10 | 122.6 (4) | H9A—C9—H9C | 109.5 |
C3—C2—C10 | 120.4 (4) | H9B—C9—H9C | 109.5 |
C4—C3—C2 | 118.4 (4) | C2—C10—H10A | 109.5 |
C4—C3—C11 | 121.1 (4) | C2—C10—H10B | 109.5 |
C2—C3—C11 | 120.5 (5) | H10A—C10—H10B | 109.5 |
C3—C4—C5 | 123.1 (4) | C2—C10—H10C | 109.5 |
C3—C4—H4 | 118.4 | H10A—C10—H10C | 109.5 |
C5—C4—H4 | 118.4 | H10B—C10—H10C | 109.5 |
C6—C5—C4 | 119.7 (5) | C3—C11—H11A | 109.5 |
C6—C5—H5 | 120.2 | C3—C11—H11B | 109.5 |
C4—C5—H5 | 120.2 | H11A—C11—H11B | 109.5 |
C5—C6—C1 | 117.7 (4) | C3—C11—H11C | 109.5 |
C5—C6—H6 | 121.2 | H11A—C11—H11C | 109.5 |
C1—C6—H6 | 121.2 | H11B—C11—H11C | 109.5 |
C7—N1—C1—C2 | 83.6 (5) | C11—C3—C4—C5 | 179.5 (4) |
C7—N1—C1—C6 | −99.9 (4) | C3—C4—C5—C6 | −0.6 (7) |
C6—C1—C2—C3 | −0.4 (5) | C4—C5—C6—C1 | 0.8 (6) |
N1—C1—C2—C3 | 175.8 (3) | C2—C1—C6—C5 | −0.3 (6) |
C6—C1—C2—C10 | 179.3 (3) | N1—C1—C6—C5 | −176.6 (4) |
N1—C1—C2—C10 | −4.4 (5) | C1—N1—C7—N2 | 179.8 (3) |
C1—C2—C3—C4 | 0.7 (6) | C1—N1—C7—S1 | −0.1 (5) |
C10—C2—C3—C4 | −179.1 (4) | C8—N2—C7—N1 | 2.3 (6) |
C1—C2—C3—C11 | −179.0 (4) | C8—N2—C7—S1 | −177.8 (3) |
C10—C2—C3—C11 | 1.2 (6) | C7—N2—C8—O1 | −5.1 (6) |
C2—C3—C4—C5 | −0.2 (7) | C7—N2—C8—C9 | 174.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 (2) | 1.97 (3) | 2.664 (4) | 137 (3) |
N1—H1N···O1i | 0.86 (2) | 2.50 (3) | 3.168 (4) | 136 (3) |
N2—H2N···S1ii | 0.84 (2) | 2.54 (2) | 3.378 (3) | 176 (3) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C11H14N2OS |
Mr | 222.30 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.0552 (7), 9.869 (2), 12.028 (3) |
α, β, γ (°) | 106.71 (1), 91.01 (1), 94.57 (1) |
V (Å3) | 572.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.48 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.886, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3414, 2066, 1331 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.141, 1.08 |
No. of reflections | 2066 |
No. of parameters | 145 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.24 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.856 (18) | 1.97 (3) | 2.664 (4) | 137 (3) |
N1—H1N···O1i | 0.856 (18) | 2.50 (3) | 3.168 (4) | 136 (3) |
N2—H2N···S1ii | 0.838 (18) | 2.542 (19) | 3.378 (3) | 176 (3) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z. |
Acknowledgements
BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.
References
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Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They are known to exhibit a wide variety of biological activities. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Jyothi & Gowda, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,3-dimethylphenyl)thiourea has been determined (Fig. 1).
The conformation of the two N—H bonds are anti to each other, and one of them is anti to the C═S in the urea segment and the other orients away from it. The adjacent N—H bond is anti to the ortho- and meta-methyl groups in the benzene ring. Furthermore, the conformations of the amide C═S and the C═O are anti to each other, similar to the anti conformation observed in 3-acetyl-1-(2-methylphenyl)thiourea (Shahwar et al., 2012).
The side chain is oriented itself with respect to the phenyl ring with the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = - 99.89 (44)°. The dihedral angle between the phenyl ring and the side chain is 81.33 (10)°.
The hydrogen atom of the NH attached to the phenyl ring and the amide oxygen exhibit a bifurcated hydrogen bonding by showing the simultaneous intra and intermolecular hydrogen bonding. In the crystal, the molecules form inversion type dimers which are linked into infinite chains in terms of R22(12) and R22(8) networks through series of N—H···O and N—H···S intermolecular hydrogen bonds, respectively (Table 1, Fig.2).