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ISSN: 2056-9890

2-(4-Chloro­anilino)-1-phenyl­ethanone

aCollege of Chemistry and Chemical Engineering, Liaocheng University, 252059 Liaocheng, Shandong, People's Republic of China, and bGuodian Liaocheng Power Co. Ltd, 252033 Liaocheng, Shandong, People's Republic of China
*Correspondence e-mail: y_xingjun01@163.com

(Received 16 February 2011; accepted 20 February 2011; online 26 February 2011)

In the title compound, C14H12ClNO, the planes of the two aromatic rings form a dihedral angle of 4.16 (1)°. The mol­ecule is essentially planar with an r.m.s. deviation for all non-H atoms of 0.0372 Å.

Related literature

For a related structure, see: Anilkumar et al. (2005[Anilkumar, H. G., Yathirajan, H. S., Nagaraja, P. & Bolte, M. (2005). Acta Cryst. E61, o2551-o2552.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO

  • Mr = 245.70

  • Triclinic, [P \overline 1]

  • a = 5.6500 (5) Å

  • b = 7.3921 (8) Å

  • c = 13.9769 (14) Å

  • α = 98.588 (2)°

  • β = 91.095 (1)°

  • γ = 97.590 (1)°

  • V = 571.70 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 298 K

  • 0.15 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.969

  • 2924 measured reflections

  • 1971 independent reflections

  • 1238 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.178

  • S = 1.03

  • 1971 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, C14H12ClNO, is often used as catalyst for the polymerization of olefins and as a reactant in organic synthesis. The molecule of (I) is shown in Fig. 1. The bond lengths and angles are normal. The dihedral angle between the two benzene rings is 4.16 (1) °. The molecule is essentially planar, the r.m.s. deviation for all non-H atoms being 0.0372 Å.

Related literature top

For a related structure, see: Anilkumar et al. (2005).

Experimental top

The title compound was synthesized by the reaction of 4-chloroaniline (1 mmol, 127.6 mg) with 2-bromo-1-phenylethanone (1 mmol, 199.0 mg) in ethanol (20 ml) under reflux conditions (338 K) for 3 h. The solvent was removed and the solid product recrystallized from ethanol. After six days brown crystals were obtained that were suitable for X-ray diffraction study.

Refinement top

All H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding atoms. For those bound to C, Uiso(H) = 1.2 or 1.5 Ueq(C) whereas for those bound to N, Uiso(H) = 1.5 Ueq(N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound showing the atomic labeling and 30% probability displacement ellipsoids.
2-(4-Chloroanilino)-1-phenylethanone top
Crystal data top
C14H12ClNOZ = 2
Mr = 245.70F(000) = 256
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6500 (5) ÅCell parameters from 945 reflections
b = 7.3921 (8) Åθ = 2.8–24.4°
c = 13.9769 (14) ŵ = 0.31 mm1
α = 98.588 (2)°T = 298 K
β = 91.095 (1)°Block, brown
γ = 97.590 (1)°0.15 × 0.12 × 0.10 mm
V = 571.70 (10) Å3
Data collection top
Bruker SMART APEX
diffractometer
1971 independent reflections
Radiation source: fine-focus sealed tube1238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 66
Tmin = 0.954, Tmax = 0.969k = 78
2924 measured reflectionsl = 1316
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1P)2 + 0.0005P]
where P = (Fo2 + 2Fc2)/3
1971 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C14H12ClNOγ = 97.590 (1)°
Mr = 245.70V = 571.70 (10) Å3
Triclinic, P1Z = 2
a = 5.6500 (5) ÅMo Kα radiation
b = 7.3921 (8) ŵ = 0.31 mm1
c = 13.9769 (14) ÅT = 298 K
α = 98.588 (2)°0.15 × 0.12 × 0.10 mm
β = 91.095 (1)°
Data collection top
Bruker SMART APEX
diffractometer
1971 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1238 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.969Rint = 0.032
2924 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.03Δρmax = 0.44 e Å3
1971 reflectionsΔρmin = 0.36 e Å3
154 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
Cl10.43122 (17)0.65041 (13)0.83483 (7)0.0650 (4)
N10.1395 (5)0.7998 (4)0.5053 (2)0.0506 (8)
H10.28520.84980.51790.061*
O10.4464 (4)0.8715 (3)0.37523 (18)0.0598 (7)
C10.0566 (6)0.7594 (4)0.4079 (2)0.0413 (8)
H1A0.07640.82660.39880.050*
H1B0.00050.62850.39200.050*
C20.2487 (6)0.8107 (4)0.3420 (2)0.0415 (8)
C30.1916 (5)0.7858 (4)0.2383 (2)0.0405 (8)
C40.0282 (6)0.7083 (4)0.1998 (2)0.0533 (9)
H40.14670.66760.23990.064*
C50.0752 (7)0.6900 (5)0.1028 (3)0.0706 (12)
H50.22550.63650.07690.085*
C60.0965 (8)0.7495 (5)0.0435 (3)0.0737 (12)
H60.06340.73770.02280.088*
C70.3167 (8)0.8265 (5)0.0813 (3)0.0700 (12)
H70.43480.86710.04100.084*
C80.3635 (6)0.8438 (4)0.1780 (2)0.0536 (10)
H80.51460.89590.20360.064*
C90.0012 (5)0.7637 (4)0.5807 (2)0.0363 (7)
C100.0950 (6)0.8121 (4)0.6740 (2)0.0424 (8)
H100.25200.86950.68420.051*
C110.0353 (6)0.7783 (4)0.7514 (2)0.0446 (8)
H110.03130.81290.81390.054*
C120.2643 (6)0.6932 (4)0.7368 (2)0.0412 (8)
C130.3618 (6)0.6439 (4)0.6462 (3)0.0449 (8)
H130.51850.58540.63690.054*
C140.2313 (6)0.6795 (4)0.5679 (2)0.0445 (8)
H140.30040.64660.50570.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0711 (7)0.0651 (7)0.0599 (7)0.0021 (5)0.0184 (5)0.0176 (5)
N10.0441 (17)0.0607 (19)0.0426 (18)0.0048 (14)0.0015 (13)0.0045 (14)
O10.0500 (16)0.0705 (18)0.0540 (16)0.0095 (13)0.0005 (13)0.0097 (13)
C10.0433 (19)0.0377 (19)0.042 (2)0.0048 (15)0.0009 (16)0.0047 (15)
C20.044 (2)0.0269 (17)0.053 (2)0.0003 (15)0.0030 (17)0.0074 (14)
C30.050 (2)0.0285 (17)0.043 (2)0.0070 (15)0.0045 (16)0.0044 (14)
C40.054 (2)0.060 (2)0.044 (2)0.0007 (18)0.0003 (18)0.0076 (17)
C50.069 (3)0.082 (3)0.057 (3)0.003 (2)0.011 (2)0.006 (2)
C60.099 (4)0.077 (3)0.045 (2)0.009 (3)0.001 (2)0.015 (2)
C70.091 (3)0.062 (3)0.057 (3)0.003 (2)0.020 (2)0.018 (2)
C80.063 (2)0.044 (2)0.051 (2)0.0021 (17)0.0072 (18)0.0044 (16)
C90.0419 (18)0.0278 (17)0.0393 (19)0.0074 (14)0.0003 (15)0.0032 (13)
C100.0364 (17)0.0358 (19)0.053 (2)0.0030 (14)0.0031 (16)0.0059 (15)
C110.050 (2)0.044 (2)0.0389 (19)0.0025 (16)0.0033 (16)0.0058 (15)
C120.046 (2)0.0348 (18)0.045 (2)0.0078 (15)0.0086 (16)0.0104 (14)
C130.0369 (18)0.041 (2)0.054 (2)0.0004 (15)0.0013 (16)0.0021 (16)
C140.043 (2)0.048 (2)0.0388 (19)0.0025 (16)0.0054 (16)0.0010 (15)
Geometric parameters (Å, º) top
Cl1—C121.723 (3)C6—C71.360 (5)
N1—C91.361 (4)C6—H60.9300
N1—C11.407 (4)C7—C81.356 (5)
N1—H10.8600C7—H70.9300
O1—C21.204 (4)C8—H80.9300
C1—C21.485 (4)C9—C141.374 (4)
C1—H1A0.9700C9—C101.376 (5)
C1—H1B0.9700C10—C111.355 (4)
C2—C31.457 (4)C10—H100.9300
C3—C41.362 (4)C11—C121.359 (5)
C3—C81.367 (4)C11—H110.9300
C4—C51.360 (4)C12—C131.350 (5)
C4—H40.9300C13—C141.370 (4)
C5—C61.359 (4)C13—H130.9300
C5—H50.9300C14—H140.9300
C9—N1—C1123.4 (3)C8—C7—C6119.8 (3)
C9—N1—H1118.3C8—C7—H7120.1
C1—N1—H1118.3C6—C7—H7120.1
N1—C1—C2111.2 (3)C7—C8—C3120.9 (3)
N1—C1—H1A109.4C7—C8—H8119.6
C2—C1—H1A109.4C3—C8—H8119.6
N1—C1—H1B109.4N1—C9—C14122.6 (3)
C2—C1—H1B109.4N1—C9—C10119.6 (3)
H1A—C1—H1B108.0C14—C9—C10117.8 (3)
O1—C2—C3121.9 (3)C11—C10—C9121.8 (3)
O1—C2—C1119.4 (3)C11—C10—H10119.1
C3—C2—C1118.7 (3)C9—C10—H10119.1
C4—C3—C8119.0 (3)C10—C11—C12119.3 (3)
C4—C3—C2122.2 (3)C10—C11—H11120.3
C8—C3—C2118.9 (3)C12—C11—H11120.3
C5—C4—C3120.3 (3)C13—C12—C11120.4 (3)
C5—C4—H4119.9C13—C12—Cl1120.0 (3)
C3—C4—H4119.9C11—C12—Cl1119.6 (3)
C6—C5—C4120.3 (4)C12—C13—C14120.4 (3)
C6—C5—H5119.9C12—C13—H13119.8
C4—C5—H5119.9C14—C13—H13119.8
C5—C6—C7119.9 (4)C13—C14—C9120.3 (3)
C5—C6—H6120.1C13—C14—H14119.9
C7—C6—H6120.1C9—C14—H14119.9
C9—N1—C1—C2178.9 (3)C2—C3—C8—C7178.8 (3)
N1—C1—C2—O12.6 (4)C1—N1—C9—C141.8 (5)
N1—C1—C2—C3177.4 (2)C1—N1—C9—C10178.3 (3)
O1—C2—C3—C4176.5 (3)N1—C9—C10—C11179.7 (3)
C1—C2—C3—C43.5 (4)C14—C9—C10—C110.1 (5)
O1—C2—C3—C84.2 (4)C9—C10—C11—C120.5 (5)
C1—C2—C3—C8175.8 (2)C10—C11—C12—C130.4 (5)
C8—C3—C4—C50.3 (2)C10—C11—C12—Cl1179.8 (2)
C2—C3—C4—C5179.0 (3)C11—C12—C13—C140.2 (5)
C3—C4—C5—C60.2 (2)Cl1—C12—C13—C14179.2 (2)
C4—C5—C6—C70.5 (4)C12—C13—C14—C90.8 (5)
C5—C6—C7—C80.2 (5)N1—C9—C14—C13179.0 (3)
C6—C7—C8—C30.4 (5)C10—C9—C14—C130.8 (5)
C4—C3—C8—C70.6 (4)

Experimental details

Crystal data
Chemical formulaC14H12ClNO
Mr245.70
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)5.6500 (5), 7.3921 (8), 13.9769 (14)
α, β, γ (°)98.588 (2), 91.095 (1), 97.590 (1)
V3)571.70 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.954, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
2924, 1971, 1238
Rint0.032
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.178, 1.03
No. of reflections1971
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

 

References

First citationAnilkumar, H. G., Yathirajan, H. S., Nagaraja, P. & Bolte, M. (2005). Acta Cryst. E61, o2551–o2552.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  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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