organic papers
Acta Cryst.(2005). E61, o389±o390 doi:10.1107/S1600536805001145 Taiet al. C10H10ClNO2
o389
Acta Crystallographica Section EStructure 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
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)x1 2;y;ÿz32.
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
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 Kα 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
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
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