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Acta Cryst.(2005). E61, o389±o390 doi:10.1107/S1600536805001145 Taiet al. C10H10ClNO2

o389

Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

2-Acetyl-3

000

-chloroacetanilide

Xi-Shi Tai,a* Wan-Yi Liu,b

Yan-Zhen Liuaand Yi-Zhi Lic

aDepartment of Chemistry, Weifang University,

Weifang 261061, People's Republic of China,

bNingXia Natural Gas Transferring Key

Laboratory, NingXia University, Yinchuan 750021, People's Republic of China, and

cCoordination Chemistry Institute, State Key

Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China

Correspondence e-mail: taixishi@lzu.edu.cn

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.003 AÊ Rfactor = 0.041 wRfactor = 0.075

Data-to-parameter ratio = 15.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography Printed in Great Britain ± all rights reserved

In the title compound [alternatively called N -(3-chloro-phenyl)-3-oxobutanamide], C10H10ClNO2, the C O bond

lengths are 1.2108 (19) and 1.179 (2) AÊ, which implies that the molecule is in the keto form. The crystal structure is stabilized by an NÐH O hydrogen bond.

Comment

Europium(III) and terbium(III) complexes with conjugated ligands having a -diketonate group have been studied as emitting materials for organic electroluminescent diodes (OLED) (Kidoet al., 1991, 1993; Takadaet al., 1994; Huanget al., 2001), since the initial reports by Kido et al. (1990). However, the quantum ef®ciency of most of these complexes is unfortunately still low. This may be due mainly to the inef®ciency of the energy transfer, in particular triplet±triplet transfer, in these complexes. Chemists have realised that it is essential to design ligands which have better energy-transfer properties to the lanthanide metal ion. In the present work, as part of our studies of the synthesis and characterization of

-diketonate-type ligands and their complexes, we have synthesized the title compound, (I), and determined its crystal structure. The crystal structures of similar compounds, namely 20-chloroacetoacetanilide and 40-chloroacetoacetanilide, were reported by Kubozonoet al. (1992).

In the molecule of (I), the C O bond lengths are 1.2108 (19) and 1.179 (2) AÊ, which con®rms that the compound is in the keto form (Fig. 1).

Received 4 January 2005 Accepted 12 January 2005 Online 22 January 2005

Figure 1

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The crystal structure of (I) is stabilized by an NÐH O intermolecular hydrogen bond (Fig. 2).

Experimental

The title compound was prepared by a method similar to that of Lliopouloset al. (1986). A solution of 3-chloroaniline (10 mmol) in benzene (30 ml) was added to a solution of ethyl acetoacetate (10 mmol) and the reaction mixture was re¯uxed for 2 h with stirring. The resulting pale precipitate was collected by ®ltration, washed several times with benzene and driedin vacuo(yield 89%). Analysis: MS for C10H10ClNO2: M+H = 212 (found), M= 211 (calculated); calculated: C 56.74, H 4.73, N 6.62%; found: C 56.58, H 4.72, N 6.48%; IR (KBr, cmÿ1): 3240 (m, NÐH), 1722 (s, CH

3C O), 1664 (s, amide C O). An ethanol solution of the title compound was allowed to evaporate slowly and pale crystals of (I) were obtained after a week.

Crystal data C10H10ClNO2

Mr= 211.64

Orthorhombic,Pbca a= 9.5485 (16) AÊ

b= 8.2197 (13) AÊ

c= 25.940 (4) AÊ

V= 2035.9 (6) AÊ3

Z= 8

Dx= 1.381 Mg mÿ3

MoKradiation Cell parameters from 702

re¯ections

= 2.6±18.3

= 0.35 mmÿ1

T= 293 (2) K Block, colourless 0.320.260.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

'and!scans

Absorption correction: multi-scan (SADABS; Bruker, 2000)

Tmin= 0.90,Tmax= 0.92 10 164 measured re¯ections

1988 independent re¯ections 1285 re¯ections withI> 2(I)

Rint= 0.046

max= 26.0

h=ÿ11!11

k=ÿ7!10

l=ÿ29!31 Refinement

Re®nement onF2

R[F2> 2(F2)] = 0.041

wR(F2) = 0.075

S= 0.98 1988 re¯ections 128 parameters

H-atom parameters constrained

w= 1/[2(F

o2) + (0.03P)2] whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.14 e AÊÿ3

min=ÿ0.14 e AÊÿ3 Extinction correction: none

Table 1

Hydrogen-bond geometry (AÊ,).

DÐH A DÐH H A D A DÐH A

N1ÐH1 O1i 0.86 2.09 2.9259 (18) 163

Symmetry code: (i)x‡1 2;y;ÿz‡32.

All H atoms were positioned geometrically, with CÐH distances in the range 0.93±0.97 AÊ and an NÐH distance of 0.86 AÊ, and they were treated as riding, withUiso(H) = 1.2Ueq(C,N), or 1.5Ueq(C) for methyl H atoms.

Data collection:SMART(Bruker, 2000); cell re®nement:SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.

The authors thank the National Natural Science Foundation of China (grant No. 20441002), NingXia Natural Gas Trans-ferring Key Laboratory (grant No. 2004007) and Weifang University for research grants.

References

Bruker (2000).SMART,SAINTandSHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Huang, L., Wang, K. Z., Huang, C. H., Li, F. Y. & Huang, Y. Y. (2001).J. Mater. Chem.11, 790±793.

Kido, J., Nagai, K. & Okamoto, Y. (1990).Chem. Lett.pp. 657±659. Kido, J., Nagai, K. & Okamoto, Y. (1991).Chem. Lett.pp. 1267±1269. Kido, J., Nagai, K. & Okamoto, Y. (1993).J. Alloys Compd.192, 30±33. Kubozono, Y., Kohno, I., Ooishi, K., Namazue, S., Haisa, M. & Kashino, S.

(1992).Bull. Chem. Soc. Jpn,65, 3234±3240.

Lliopoulos, P., Fallon, G. D. & Murray, S. (1986).J. Chem. Soc. Dalton Trans.

pp. 437±443.

Takada, N., Tsutsui, T. & Saito, S. (1994).Jpn. J. Appl. Phys. 33, L863± L866.

Figure 2

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supporting information

sup-1

Acta Cryst. (2005). E61, o389–o390

supporting information

Acta Cryst. (2005). E61, o389–o390 [https://doi.org/10.1107/S1600536805001145]

2-Acetyl-3

-chloroacetanilide

Xi-Shi Tai, Wan-Yi Liu, Yan-Zhen Liu and Yi-Zhi Li

N-(3-chlorophenyl)-3-oxobutanamide

Crystal data

C10H10ClNO2 Mr = 211.64

Orthorhombic, Pbca Hall symbol: -P 2ac 2ab a = 9.5485 (16) Å b = 8.2197 (13) Å c = 25.940 (4) Å V = 2035.9 (6) Å3

Z = 8

F(000) = 880 Dx = 1.381 Mg m−3

Mo radiation, λ = 0.71073 Å Cell parameters from 702 reflections θ = 2.6–18.3°

µ = 0.35 mm−1 T = 293 K Plate, colourless 0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Radiation source: sealed tube Graphite monochromator φ and ω scans

Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin = 0.90, Tmax = 0.92

10164 measured reflections 1988 independent reflections 1285 reflections with I > 2σ(I) Rint = 0.046

θmax = 26.0°, θmin = 2.7° h = −11→11

k = −7→10 l = −29→31

Refinement

Refinement on F2

Least-squares matrix: full R[F2 > 2σ(F2)] = 0.041 wR(F2) = 0.075 S = 0.98 1988 reflections 128 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2(F

o2) + (0.03P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Special details

Experimental. All commercially available reagents were used as supplied. Carbon, hydrogen and nitrogen were

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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)

x y z Uiso*/Ueq

Cl1 0.58989 (7) 0.23432 (7) 0.52633 (2) 0.0703 (2) N1 0.42667 (13) 0.25024 (16) 0.71108 (5) 0.0385 (3) H1 0.5134 0.2364 0.7189 0.046* O1 0.20787 (11) 0.24572 (17) 0.74412 (5) 0.0572 (4) O2 0.36625 (18) 0.42013 (18) 0.83242 (6) 0.0734 (5) C1 0.39771 (17) 0.29927 (19) 0.66060 (7) 0.0339 (4) C2 0.49338 (19) 0.2525 (2) 0.62307 (7) 0.0410 (4) H2 0.5719 0.1920 0.6320 0.049* C3 0.4714 (2) 0.2960 (2) 0.57296 (7) 0.0445 (5) C4 0.3579 (2) 0.3849 (2) 0.55802 (8) 0.0552 (5) H4 0.3438 0.4135 0.5237 0.066* C5 0.2656 (2) 0.4300 (3) 0.59573 (9) 0.0561 (6) H5 0.1875 0.4912 0.5866 0.067* C6 0.28399 (19) 0.3882 (2) 0.64642 (7) 0.0481 (5) H6 0.2189 0.4206 0.6710 0.058* C7 0.33240 (17) 0.2223 (2) 0.74891 (7) 0.0361 (4) C8 0.39229 (17) 0.1587 (2) 0.79803 (7) 0.0387 (4) H8A 0.4885 0.1256 0.7921 0.046* H8B 0.3399 0.0632 0.8085 0.046* C9 0.38898 (19) 0.2817 (3) 0.84083 (8) 0.0499 (5) C10 0.4198 (3) 0.2174 (3) 0.89323 (9) 0.0753 (7) H10A 0.4216 0.3057 0.9175 0.113* H10B 0.5092 0.1640 0.8930 0.113* H10C 0.3485 0.1411 0.9030 0.113*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

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supporting information

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Acta Cryst. (2005). E61, o389–o390

C6 0.0367 (11) 0.0554 (12) 0.0523 (12) 0.0097 (9) −0.0101 (9) −0.0048 (10) C7 0.0267 (9) 0.0366 (9) 0.0450 (10) 0.0019 (7) 0.0022 (7) −0.0050 (8) C8 0.0266 (8) 0.0406 (10) 0.0489 (11) 0.0005 (7) 0.0033 (8) 0.0102 (7) C9 0.0366 (10) 0.0527 (13) 0.0605 (12) 0.0069 (10) −0.0064 (9) 0.0054 (9) C10 0.0644 (15) 0.1007 (19) 0.0609 (15) 0.0202 (15) −0.0061 (12) 0.0081 (13)

Geometric parameters (Å, º)

Cl1—C3 1.7322 (19) C4—H4 0.9300 N1—C7 1.351 (2) C5—C6 1.370 (3) N1—C1 1.398 (2) C5—H5 0.9300 N1—H1 0.8600 C6—H6 0.9300 O1—C7 1.2108 (19) C7—C8 1.491 (2) O2—C9 1.179 (2) C8—C9 1.502 (3) C1—C6 1.360 (2) C8—H8A 0.9700 C1—C2 1.389 (2) C8—H8B 0.9700 C2—C3 1.364 (3) C9—C10 1.488 (3) C2—H2 0.9300 C10—H10A 0.9600 C3—C4 1.363 (3) C10—H10B 0.9600 C4—C5 1.368 (3) C10—H10C 0.9600

C7—N1—C1 126.69 (14) C5—C6—H6 120.1 C7—N1—H1 116.7 O1—C7—N1 123.56 (17) C1—N1—H1 116.7 O1—C7—C8 121.33 (17) C6—C1—C2 118.95 (17) N1—C7—C8 115.11 (14) C6—C1—N1 124.51 (16) C7—C8—C9 112.82 (15) C2—C1—N1 116.54 (15) C7—C8—H8A 109.0 C3—C2—C1 119.61 (17) C9—C8—H8A 109.0 C3—C2—H2 120.2 C7—C8—H8B 109.0 C1—C2—H2 120.2 C9—C8—H8B 109.0 C4—C3—C2 122.25 (18) H8A—C8—H8B 107.8 C4—C3—Cl1 118.53 (15) O2—C9—C10 123.3 (2) C2—C3—Cl1 119.22 (14) O2—C9—C8 121.10 (18) C3—C4—C5 117.01 (19) C10—C9—C8 115.62 (19) C3—C4—H4 121.5 C9—C10—H10A 109.5 C5—C4—H4 121.5 C9—C10—H10B 109.5 C4—C5—C6 122.40 (18) H10A—C10—H10B 109.5 C4—C5—H5 118.8 C9—C10—H10C 109.5 C6—C5—H5 118.8 H10A—C10—H10C 109.5 C1—C6—C5 119.78 (18) H10B—C10—H10C 109.5 C1—C6—H6 120.1

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N1—H1···O1i 0.86 2.09 2.9259 (18) 163

References

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