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2-(2-Chloro­phen­yl)-2-oxo-N-phenyl­acetamide

aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
*Correspondence e-mail: wyz@zju.edu.cn

(Received 30 August 2011; accepted 26 October 2011; online 2 November 2011)

In the title compound, C14H10ClNO2, the dihedral angle between the two rings is 59.4 (2)°. The two carbonyl groups are oriented almost anti­periplanar to each other, with a torsion angle of −160.43 (2)°. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds.

Related literature

The crystal structure of the title compound was determined within a project on the synthesis of new phenylacetamides, see: Li & Wu (2010[Li, H. M. & Wu, J.-L. (2010). Acta Cryst. E66, o1274.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10ClNO2

  • Mr = 259.68

  • Monoclinic, P 21 /c

  • a = 11.3513 (11) Å

  • b = 10.4585 (8) Å

  • c = 10.2944 (10) Å

  • β = 100.954 (10)°

  • V = 1199.86 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 293 K

  • 0.48 × 0.39 × 0.25 mm

Data collection
  • Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]) Tmin = 0.860, Tmax = 0.928

  • 5282 measured reflections

  • 2201 independent reflections

  • 1562 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.095

  • S = 1.01

  • 2201 reflections

  • 163 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N—H⋯O1i 0.86 2.52 3.241 (4) 141
Symmetry code: (i) -x, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Related literature top

The crystal structure of the title compound was determined within a project on the synthesis of new phenylacetamides, see: Li & Wu (2010).

Experimental top

A solution of 2-chloroacetophenone (1.0 g, 6.5 mmol) and SeO2 (1.94 g, 16.8 mmol) in 10 ml of freshly distilled pyridine was heated to 383 K. The reaction mixture was gradually cooled down to 363 K over 1 h and was kept at thistemperature for additional 4 h. The solution was concentrated using a rotary evaporator until a small amount of liquid was present. The black selenium was rinsed several times with ethyl acetate. The combined organic layers were acidified with 10 ml of 0.1 M HC1 and the aqueous layer was extracted three times with ethyl acetate. The organic layers were combined and extracted several times with saturated aqueous NaHC03. The aqueous layers were combined, brought to pH 1 with conc. HCl and extracted three times with ethyl acetate. The final organic layers were dried over anhydrous Na2SO4 and concentrated, producing (2-chlorophenyl)glyoxylic acid in 85% yield (1.02 g) as a solid.

Into a suspension of (2-chlorophenyl)glyoxylic acid (250 mg, 1.36 mmol) and aniline (116 mg, 1.25 mmol) in methylene chloride (8 ml), N,N'-dicyclohexylcarbodiimide (DCC) (280 mg, 1.36 mmol) and 4-(dimethylamino)pyridine (DMAP) (33 mg, 0.27 mmol) was added respectively at room temperature and continuted stirring for 8 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, the residue was purified by colum chromatography (silica gel, 30% of ethyl acetate in hexane) to afford the title compound in 72% yield (254 mg) as a white solid, m.p. 349–351 K, 1H NMR (400 MHz, CDCl3) /d 8.79 (brs, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.53–7.47 (m, 2H), 7.40 (t, J = 8.0 Hz, 3H), 7.21 (t, J = 7.6 Hz, 1H). Single crystals suitable for X-ray diffraction of the title compound were grown in a micture of ethyl acetate and hexane.

Refinement top

The H atoms were placed in calculated positions with C—H = 0.93 Å and refined isotropic with Uiso(H) =1.2Ueq of the carrier atom using a riding model.

Structure description top

The crystal structure of the title compound was determined within a project on the synthesis of new phenylacetamides, see: Li & Wu (2010).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 40% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. The dimer of the title compound linked by two N—H···O hydrogen bonds (dotted lines).
2-(2-Chlorophenyl)-2-oxo-N-phenylacetamide top
Crystal data top
C14H10ClNO2F(000) = 536
Mr = 259.68Dx = 1.438 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1968 reflections
a = 11.3513 (11) Åθ = 3.5–29.2°
b = 10.4585 (8) ŵ = 0.31 mm1
c = 10.2944 (10) ÅT = 293 K
β = 100.954 (10)°Block, yellow
V = 1199.86 (19) Å30.48 × 0.39 × 0.25 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini ultra
diffractometer
2201 independent reflections
Radiation source: fine-focus sealed tube1562 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 10.3592 pixels mm-1θmax = 25.4°, θmin = 3.6°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 1112
Tmin = 0.860, Tmax = 0.928l = 127
5282 measured reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0552P)2]
where P = (Fo2 + 2Fc2)/3
2201 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C14H10ClNO2V = 1199.86 (19) Å3
Mr = 259.68Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.3513 (11) ŵ = 0.31 mm1
b = 10.4585 (8) ÅT = 293 K
c = 10.2944 (10) Å0.48 × 0.39 × 0.25 mm
β = 100.954 (10)°
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini ultra
diffractometer
2201 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
1562 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.928Rint = 0.021
5282 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.01Δρmax = 0.14 e Å3
2201 reflectionsΔρmin = 0.19 e Å3
163 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
xyzUiso*/Ueq
Cl0.39169 (4)0.11424 (5)0.07892 (5)0.0671 (2)
O10.12583 (11)0.05846 (11)0.01363 (12)0.0534 (4)
O20.04597 (11)0.32465 (12)0.20894 (12)0.0556 (4)
N0.05486 (12)0.13663 (13)0.20367 (13)0.0438 (4)
H0.04820.06370.16430.053*
C10.13889 (17)0.38201 (17)0.07314 (17)0.0505 (5)
H10.06090.39860.02950.061*
C20.1960 (2)0.46949 (19)0.16282 (18)0.0627 (5)
H20.15630.54320.18110.075*
C30.3117 (2)0.4475 (2)0.2250 (2)0.0697 (6)
H30.35080.50670.28560.084*
C40.37045 (18)0.3389 (2)0.19889 (19)0.0637 (6)
H40.44950.32540.24070.076*
C50.31215 (15)0.24881 (17)0.10994 (18)0.0483 (5)
C60.19425 (14)0.26908 (16)0.04560 (16)0.0409 (4)
C70.12143 (13)0.17184 (16)0.03847 (16)0.0404 (4)
C80.03285 (14)0.22088 (16)0.16030 (16)0.0406 (4)
C90.15676 (14)0.15162 (15)0.30543 (16)0.0386 (4)
C100.24427 (14)0.05916 (17)0.31498 (16)0.0449 (4)
H100.23310.01090.25830.054*
C110.34801 (16)0.07007 (19)0.40792 (19)0.0572 (5)
H110.40740.00800.41350.069*
C120.36407 (17)0.1729 (2)0.49283 (19)0.0609 (5)
H120.43450.18060.55530.073*
C130.27627 (18)0.26376 (18)0.48528 (18)0.0567 (5)
H130.28740.33260.54360.068*
C140.17155 (16)0.25492 (16)0.39263 (17)0.0480 (5)
H140.11200.31660.38840.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0447 (3)0.0726 (4)0.0818 (4)0.0070 (2)0.0062 (2)0.0104 (3)
O10.0500 (7)0.0414 (7)0.0634 (8)0.0033 (6)0.0028 (6)0.0056 (6)
O20.0601 (8)0.0440 (8)0.0578 (8)0.0130 (6)0.0017 (6)0.0081 (6)
N0.0394 (8)0.0385 (8)0.0499 (9)0.0037 (6)0.0002 (7)0.0092 (6)
C10.0499 (11)0.0514 (11)0.0501 (11)0.0042 (9)0.0089 (9)0.0006 (9)
C20.0786 (15)0.0572 (12)0.0541 (12)0.0067 (11)0.0174 (11)0.0115 (10)
C30.0906 (17)0.0681 (15)0.0469 (11)0.0216 (13)0.0042 (11)0.0083 (10)
C40.0551 (12)0.0788 (15)0.0501 (11)0.0204 (11)0.0075 (9)0.0080 (11)
C50.0444 (10)0.0534 (11)0.0467 (10)0.0062 (8)0.0077 (8)0.0080 (8)
C60.0405 (9)0.0438 (10)0.0384 (9)0.0047 (8)0.0074 (7)0.0050 (7)
C70.0352 (9)0.0402 (10)0.0466 (10)0.0006 (7)0.0100 (7)0.0030 (8)
C80.0385 (9)0.0397 (10)0.0441 (10)0.0034 (8)0.0087 (7)0.0006 (8)
C90.0367 (9)0.0397 (9)0.0390 (9)0.0038 (7)0.0063 (7)0.0013 (7)
C100.0412 (10)0.0442 (10)0.0485 (10)0.0028 (8)0.0070 (8)0.0030 (8)
C110.0412 (10)0.0627 (13)0.0632 (12)0.0080 (9)0.0013 (9)0.0011 (10)
C120.0484 (11)0.0669 (13)0.0597 (12)0.0075 (10)0.0091 (9)0.0009 (10)
C130.0666 (13)0.0495 (11)0.0496 (11)0.0108 (10)0.0002 (10)0.0076 (8)
C140.0524 (11)0.0401 (10)0.0497 (11)0.0034 (8)0.0053 (9)0.0023 (8)
Geometric parameters (Å, º) top
Cl—C51.7342 (19)C5—C61.392 (2)
O1—C71.2120 (19)C6—C71.481 (2)
O2—C81.2161 (19)C7—C81.539 (2)
N—C81.341 (2)C9—C101.376 (2)
N—C91.414 (2)C9—C141.394 (2)
N—H0.8600C10—C111.374 (2)
C1—C21.372 (3)C10—H100.9300
C1—C61.392 (2)C11—C121.376 (3)
C1—H10.9300C11—H110.9300
C2—C31.366 (3)C12—C131.369 (3)
C2—H20.9300C12—H120.9300
C3—C41.370 (3)C13—C141.378 (2)
C3—H30.9300C13—H130.9300
C4—C51.391 (3)C14—H140.9300
C4—H40.9300
C8—N—C9128.68 (14)C6—C7—C8116.93 (14)
C8—N—H115.7O2—C8—N126.20 (15)
C9—N—H115.7O2—C8—C7121.39 (14)
C2—C1—C6121.93 (18)N—C8—C7112.41 (14)
C2—C1—H1119.0C10—C9—C14120.10 (15)
C6—C1—H1119.0C10—C9—N116.92 (14)
C3—C2—C1119.5 (2)C14—C9—N122.98 (15)
C3—C2—H2120.3C11—C10—C9120.19 (17)
C1—C2—H2120.3C11—C10—H10119.9
C2—C3—C4120.56 (18)C9—C10—H10119.9
C2—C3—H3119.7C10—C11—C12119.99 (18)
C4—C3—H3119.7C10—C11—H11120.0
C3—C4—C5120.16 (19)C12—C11—H11120.0
C3—C4—H4119.9C13—C12—C11119.97 (17)
C5—C4—H4119.9C13—C12—H12120.0
C4—C5—C6120.28 (18)C11—C12—H12120.0
C4—C5—Cl118.15 (15)C12—C13—C14121.04 (17)
C6—C5—Cl121.54 (14)C12—C13—H13119.5
C5—C6—C1117.56 (15)C14—C13—H13119.5
C5—C6—C7123.55 (16)C13—C14—C9118.68 (16)
C1—C6—C7118.56 (14)C13—C14—H14120.7
O1—C7—C6123.52 (14)C9—C14—H14120.7
O1—C7—C8119.50 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H···O1i0.862.523.241 (4)141
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC14H10ClNO2
Mr259.68
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.3513 (11), 10.4585 (8), 10.2944 (10)
β (°) 100.954 (10)
V3)1199.86 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.48 × 0.39 × 0.25
Data collection
DiffractometerOxford Diffraction Xcalibur Atlas Gemini ultra
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.860, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
5282, 2201, 1562
Rint0.021
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.095, 1.01
No. of reflections2201
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H···O1i0.862.523.241 (4)141.1
Symmetry code: (i) x, y, z.
 

Acknowledgements

Mr Jiyong Liu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structure analysis.

References

First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.  Google Scholar
First citationLi, H. M. & Wu, J.-L. (2010). Acta Cryst. E66, o1274.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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