2-Chloro-N-methyl-N-phenyl-acetamide.

Abstract

In the title compound, C(9)H(10)ClNO, the non-H atoms, excluding the phenyl group, are almost coplanar (r.m.s. deviation of the non-H atoms = 0.1015 Å). The dihedral angle formed between this plane and the benzene ring is 87.07 (5)°. Weak inter-molecular C-H⋯O inter-actions help to stabilize the packing.

Full text

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2-Chloro-N-methyl-N-phenylacetamide
Li-Hua Zhi,aWei-Na Wu,a* Xiao-Xia Li,bYan-Wei Liaand
Yuan Wanga
aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo
454000, People’s Republic of China, andbInstitute of Functional Materials, Jiangxi
University of Finance & Economics, Nanchang 330013, People’s Republic of China
Correspondence e-mail: wuwn08@hpu.edu.cn
Received 22 November 2010; accepted 1 December 2010
Key indicators: single-crystal X-ray study; T = 296 K; mean ?(C–C) = 0.002 A ˚;
R factor = 0.044; wR factor = 0.136; data-to-parameter ratio = 27.3.
In the title compound, C9H10ClNO, the non-H atoms,
excluding the phenyl group, are almost coplanar (r.m.s.
deviation of the non-H atoms = 0.1015 A˚). The dihedral angle
formed between this plane and the benzene ring is 87.07 (5)?.
Weak intermolecular C—H???O interactions help to stabilize
the packing.
Related literature
For the synthesis of lanthanide complexes with amide-type
ligands, see: Wu et al. (2008). For related a structure, see: Yuan
et al. (2010).
Experimental
Crystal data
C9H10ClNO Mr= 183.63
Monoclinic, P21=c
a = 7.3391 (12) A˚
b = 6.5898 (10) A˚
c = 18.941 (3) A˚
? = 91.192 (9)?
V = 915.9 (2) A˚3
Z = 4
Mo K? radiation
? = 0.37 mm?1
T = 296 K
0.26 ? 0.21 ? 0.18 mm
Data collection
Bruker SMART CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
Tmin= 0.912, Tmax= 0.936
9758 measured reflections
3003 independent reflections
1869 reflections with I > 2?(I)
Rint= 0.021
Refinement
R[F2> 2?(F2)] = 0.044
wR(F2) = 0.136
S = 1.04
3003 reflections
110 parameters
H-atom parameters constrained
??max= 0.24 e A˚?3
??min= ?0.30 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
C2—H2???O1i
Symmetry code: (i) ?x þ 1;?y þ 1;?z þ 1.
D—HH???AD???AD—H???A
0.932.583.4356 (19) 154
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT
(Bruker, 2007); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure:SHELXL97 (Sheldrick,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008);moleculargraphics:
The authors are grateful to the National Natural Science
Foundation of China for financial support (grant No.
21001040).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: VM2064).
References
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA .
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207–
2215.
Yuan, M.-S., Li, Z. & Wang, Q. (2010). Acta Cryst. E66, o2017.
organic compounds
o68
Zhi et al.
doi:10.1107/S1600536810050427
Acta Cryst. (2011). E67, o68
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2011). E67, o68 [ doi:10.1107/S1600536810050427 ]
2-Chloro-N-methyl-N-phenylacetamide
L.-H. Zhi, W.-N. Wu, X.-X. Li, Y.-W. Li and Y. Wang
Comment
The luminescent properties of lanthanide complexes with amide type ligands have been investigated in our previous work
(Wu et al., 2008). As part of our ongoing studies of the amide type ligands, the title compound was synthesized and char-
acterized by X-ray diffraction.
In the title compound (Fig. 1), the C—N bond lengths are shorter than those observed in a similar compound (Yuan et
al.,2010). The non-hydrogen atoms excluding the phenyl group are almost coplanar (r.m.s. deviation of the non-hydrogen
atoms being 0.1015 Å). The dihedral angle formed between this plane and the benzene ring (r.m.s. deviation 0.0021 Å)
is 87.07 (5)°.
As expected, there are no classic hydrogen bonds in the structure. However, there is a weak intermolecular C2—H2···O1
hydrogen bond stabilizing the packing. An intramolecular C7—H7A···O1 hydrogen bond is also present (Table 1).
Experimental
A chloroform solution containing chloroacetyl chloride (2.26 g, 0.02 mol) was added dropwise to a solution of N-methyl-
benzenamine (2.14 g, 0.02 mol) and pyridine (2.60 g, 0.03 mol) in chloroform (20 ml) under stirring on an ice-water bath.
The reaction mixture was stirred at room temperature for 3.5 h. A solid product was separated from the solution by suction
filtration, purified by succesive washing with water, 0.5 mol/L HCl, 0.5 mol/L NaOH and distilled water, respectively. Col-
ourless block crystals were obtained by slow evaporation of the ethanol solution at room temperature.
Refinement
The H atoms were placed at calculated positions and refined in riding mode, with the carrier atom-H distances = 0.93 Å for
aryl, 0.97 for methylene, 0.96 Å for the methyl. The Uiso values were constrained to be 1.5Ueq of the carrier atom for the
methyl H atoms and 1.2Ueq for the remaining H atoms.
Figures
Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.

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2-Chloro-N-methyl-N-phenylacetamide
Crystal data
C9H10ClNO
F(000) = 384
Dx = 1.332 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3217 reflections
θ = 2.8–25.4°
µ = 0.37 mm−1
T = 296 K
Block, colourless
Mr = 183.63
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 7.3391 (12) Å
b = 6.5898 (10) Å
c = 18.941 (3) Å
β = 91.192 (9)°
V = 915.9 (2) Å3
Z = 4
0.26 × 0.21 × 0.18 mm
Data collection
Bruker SMART CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
Tmin = 0.912, Tmax = 0.936
9758 measured reflections
3003 independent reflections
1869 reflections with I > 2σ(I)
Rint = 0.021
θmax = 31.5°, θmin = 2.2°
h = −10→9
k = −9→9
l = −26→27
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.044
wR(F2) = 0.136
H-atom parameters constrained
S = 1.04
w = 1/[σ2(Fo2) + (0.0656P)2 + 0.0768P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.24 e Å−3
Δρmin = −0.30 e Å−3
3003 reflections
110 parameters
0 restraints
Special details
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 mat-
rix. 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

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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, convention-
al 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
0.13525 (7)
0.29635 (16)
0.2909 (2)
0.22967 (19)
0.4463 (2)
0.5533
0.1317 (2)
0.0279
0.21932 (15)
0.2821 (2)
0.2794
0.1674 (2)
0.0539
0.2575
0.4407 (2)
0.5442
0.1284 (2)
0.0214
0.3571 (3)
0.3770
0.4686
0.2656
y
0.14663 (8)
0.47779 (19)
0.3393 (2)
0.4317 (2)
0.2337 (2)
0.2483
0.3191 (3)
0.3909
0.55459 (18)
0.0864 (3)
0.0017
0.2147 (3)
0.1962
0.1252
0.1065 (3)
0.0341
0.1911 (3)
0.1758
0.6832 (3)
0.7546
0.6784
0.7523
z
0.40483 (2)
0.56727 (6)
0.62581 (7)
0.50259 (7)
0.64621 (7)
0.6212
0.66275 (8)
0.6489
0.45449 (6)
0.74123 (8)
0.7805
0.49372 (7)
0.5182
0.5154
0.70395 (8)
0.7178
0.72052 (8)
0.7455
0.58295 (10)
0.5396
0.6103
0.6093
Uiso*/Ueq
0.07202 (19)
0.0477 (3)
0.0435 (3)
0.0457 (3)
0.0494 (3)
0.059*
0.0542 (4)
0.065*
0.0632 (3)
0.0605 (4)
0.073*
0.0566 (4)
0.068*
0.068*
0.0574 (4)
0.069*
0.0620 (4)
0.074*
0.0643 (4)
0.096*
0.096*
0.096*
Cl1
N1
C1
C8
C2
H2
C6
H6
O1
C4
H4
C9
H9A
H9B
C3
H3
C5
H5
C7
H7A
H7B
H7C
Atomic displacement parameters (Å2)
U11
0.0829 (3)
0.0533 (7)
0.0526 (8)
0.0450 (7)
0.0499 (8)
0.0542 (9)
0.0722 (7)
0.0796 (11)
0.0768 (10)
0.0646 (10)
0.0650 (10)
U22
0.0883 (4)
0.0396 (7)
0.0397 (7)
0.0475 (8)
0.0490 (9)
0.0634 (10)
0.0610 (7)
0.0583 (10)
0.0539 (9)
0.0537 (9)
0.0755 (12)
U33
0.0447 (2)
0.0501 (6)
0.0379 (6)
0.0446 (7)
0.0494 (7)
0.0449 (7)
0.0563 (6)
0.0436 (8)
0.0389 (7)
0.0533 (8)
0.0459 (8)
U12
−0.0124 (2)
−0.0039 (5)
−0.0028 (6)
0.0003 (6)
−0.0004 (7)
0.0054 (7)
−0.0022 (6)
−0.0018 (8)
−0.0095 (8)
0.0065 (8)
−0.0011 (9)
U13
−0.0002 (2)
−0.0009 (5)
−0.0028 (5)
0.0043 (5)
−0.0012 (6)
0.0002 (6)
−0.0001 (5)
−0.0030 (7)
−0.0006 (7)
−0.0121 (7)
0.0085 (7)
U23
−0.00826 (18)
0.0047 (5)
−0.0021 (5)
0.0089 (5)
−0.0011 (6)
0.0026 (6)
0.0232 (5)
0.0096 (6)
0.0029 (6)
0.0034 (7)
0.0070 (7)
Cl1
N1
C1
C8
C2
C6
O1
C4
C9
C3
C5