2-Chloro-N-methyl-N-phenyl­acetamide

Zhi, L.-H.; Wu, W.-N.; Li, X.-X.; Li, Y.-W.; Wang, Y.

doi:10.1107/S1600536810050427

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o68

https://doi.org/10.1107/S1600536810050427

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2-Chloro-N-methyl-N-phenylacetamide

Li-Hua Zhi,^a Wei-Na Wu,^a ^* Xiao-Xia Li,^b Yan-Wei Li ^a and Yuan Wang ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and ^bInstitute 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; online 11 December 2010)

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 Å). 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
M_r = 183.63
Monoclinic, P 2₁ /c
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
Mo Kα radiation
μ = 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 ) T_min = 0.912, T_max = 0.936
9758 measured reflections
3003 independent reflections
1869 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.136
S = 1.04
3003 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.58	3.4356 (19)	154
Symmetry code: (i) -x+1, -y+1, -z+1.

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, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050427/vm2064sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050427/vm2064Isup2.hkl

checkCIF report

Comment top

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 characterized 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).

Related literature top

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 top

A chloroform solution containing chloroacetyl chloride (2.26 g, 0.02 mol) was added dropwise to a solution of N-methylbenzenamine (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. Colourless block crystals were obtained by slow evaporation of the ethanol solution at room temperature.

Structure description top

For the synthesis of lanthanide complexes with amide-type ligands, see: Wu et al. (2008). For related a structure, see: Yuan et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.

2-Chloro-N-methyl-N-phenylacetamide top

Crystal data top

C₉H₁₀ClNO	F(000) = 384
M_r = 183.63	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3217 reflections
a = 7.3391 (12) Å	θ = 2.8–25.4°
b = 6.5898 (10) Å	µ = 0.37 mm⁻¹
c = 18.941 (3) Å	T = 296 K
β = 91.192 (9)°	Block, colourless
V = 915.9 (2) Å³	0.26 × 0.21 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 31.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→9
T_min = 0.912, T_max = 0.936	k = −9→9
9758 measured reflections	l = −26→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0656P)² + 0.0768P] where P = (F_o² + 2F_c²)/3
3003 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₉H₁₀ClNO	V = 915.9 (2) Å³
M_r = 183.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3391 (12) Å	µ = 0.37 mm⁻¹
b = 6.5898 (10) Å	T = 296 K
c = 18.941 (3) Å	0.26 × 0.21 × 0.18 mm
β = 91.192 (9)°

Data collection top

Bruker SMART CCD diffractometer	3003 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1869 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.936	R_int = 0.021
9758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
3003 reflections	Δρ_min = −0.30 e Å⁻³
110 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

	x	y	z	U_iso*/U_eq
Cl1	0.13525 (7)	0.14663 (8)	0.40483 (2)	0.07202 (19)
N1	0.29635 (16)	0.47779 (19)	0.56727 (6)	0.0477 (3)
C1	0.2909 (2)	0.3393 (2)	0.62581 (7)	0.0435 (3)
C8	0.22967 (19)	0.4317 (2)	0.50259 (7)	0.0457 (3)
C2	0.4463 (2)	0.2337 (2)	0.64621 (7)	0.0494 (3)
H2	0.5533	0.2483	0.6212	0.059*
C6	0.1317 (2)	0.3191 (3)	0.66275 (8)	0.0542 (4)
H6	0.0279	0.3909	0.6489	0.065*
O1	0.21932 (15)	0.55459 (18)	0.45449 (6)	0.0632 (3)
C4	0.2821 (2)	0.0864 (3)	0.74123 (8)	0.0605 (4)
H4	0.2794	0.0017	0.7805	0.073*
C9	0.1674 (2)	0.2147 (3)	0.49372 (7)	0.0566 (4)
H9A	0.0539	0.1962	0.5182	0.068*
H9B	0.2575	0.1252	0.5154	0.068*
C3	0.4407 (2)	0.1065 (3)	0.70395 (8)	0.0574 (4)
H3	0.5442	0.0341	0.7178	0.069*
C5	0.1284 (2)	0.1911 (3)	0.72052 (8)	0.0620 (4)
H5	0.0214	0.1758	0.7455	0.074*
C7	0.3571 (3)	0.6832 (3)	0.58295 (10)	0.0643 (4)
H7A	0.3770	0.7546	0.5396	0.096*
H7B	0.4686	0.6784	0.6103	0.096*
H7C	0.2656	0.7523	0.6093	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0829 (3)	0.0883 (4)	0.0447 (2)	−0.0124 (2)	−0.0002 (2)	−0.00826 (18)
N1	0.0533 (7)	0.0396 (7)	0.0501 (6)	−0.0039 (5)	−0.0009 (5)	0.0047 (5)
C1	0.0526 (8)	0.0397 (7)	0.0379 (6)	−0.0028 (6)	−0.0028 (5)	−0.0021 (5)
C8	0.0450 (7)	0.0475 (8)	0.0446 (7)	0.0003 (6)	0.0043 (5)	0.0089 (5)
C2	0.0499 (8)	0.0490 (9)	0.0494 (7)	−0.0004 (7)	−0.0012 (6)	−0.0011 (6)
C6	0.0542 (9)	0.0634 (10)	0.0449 (7)	0.0054 (7)	0.0002 (6)	0.0026 (6)
O1	0.0722 (7)	0.0610 (7)	0.0563 (6)	−0.0022 (6)	−0.0001 (5)	0.0232 (5)
C4	0.0796 (11)	0.0583 (10)	0.0436 (8)	−0.0018 (8)	−0.0030 (7)	0.0096 (6)
C9	0.0768 (10)	0.0539 (9)	0.0389 (7)	−0.0095 (8)	−0.0006 (7)	0.0029 (6)
C3	0.0646 (10)	0.0537 (9)	0.0533 (8)	0.0065 (8)	−0.0121 (7)	0.0034 (7)
C5	0.0650 (10)	0.0755 (12)	0.0459 (8)	−0.0011 (9)	0.0085 (7)	0.0070 (7)
C7	0.0686 (11)	0.0438 (9)	0.0803 (11)	−0.0076 (7)	−0.0038 (9)	0.0011 (8)

Geometric parameters (Å, º) top

Cl1—C9	1.7537 (15)	C6—H6	0.9300
N1—C8	1.3446 (18)	C4—C5	1.373 (3)
N1—C1	1.4372 (17)	C4—C3	1.381 (2)
N1—C7	1.454 (2)	C4—H4	0.9300
C1—C6	1.380 (2)	C9—H9A	0.9700
C1—C2	1.384 (2)	C9—H9B	0.9700
C8—O1	1.2203 (16)	C3—H3	0.9300
C8—C9	1.509 (2)	C5—H5	0.9300
C2—C3	1.379 (2)	C7—H7A	0.9600
C2—H2	0.9300	C7—H7B	0.9600
C6—C5	1.382 (2)	C7—H7C	0.9600

C8—N1—C1	122.95 (12)	C8—C9—Cl1	112.56 (10)
C8—N1—C7	120.05 (13)	C8—C9—H9A	109.1
C1—N1—C7	116.56 (12)	Cl1—C9—H9A	109.1
C6—C1—C2	120.72 (13)	C8—C9—H9B	109.1
C6—C1—N1	119.34 (13)	Cl1—C9—H9B	109.1
C2—C1—N1	119.90 (13)	H9A—C9—H9B	107.8
O1—C8—N1	123.09 (14)	C2—C3—C4	120.20 (15)
O1—C8—C9	122.12 (13)	C2—C3—H3	119.9
N1—C8—C9	114.78 (12)	C4—C3—H3	119.9
C3—C2—C1	119.30 (14)	C4—C5—C6	120.32 (15)
C3—C2—H2	120.4	C4—C5—H5	119.8
C1—C2—H2	120.4	C6—C5—H5	119.8
C1—C6—C5	119.29 (15)	N1—C7—H7A	109.5
C1—C6—H6	120.4	N1—C7—H7B	109.5
C5—C6—H6	120.4	H7A—C7—H7B	109.5
C5—C4—C3	120.16 (15)	N1—C7—H7C	109.5
C5—C4—H4	119.9	H7A—C7—H7C	109.5
C3—C4—H4	119.9	H7B—C7—H7C	109.5

C8—N1—C1—C6	−80.39 (18)	N1—C1—C2—C3	177.81 (13)
C7—N1—C1—C6	91.92 (17)	C2—C1—C6—C5	−0.3 (2)
C8—N1—C1—C2	102.04 (17)	N1—C1—C6—C5	−177.81 (14)
C7—N1—C1—C2	−85.65 (17)	O1—C8—C9—Cl1	14.8 (2)
C1—N1—C8—O1	173.27 (13)	N1—C8—C9—Cl1	−165.31 (11)
C7—N1—C8—O1	1.2 (2)	C1—C2—C3—C4	−0.5 (2)
C1—N1—C8—C9	−6.6 (2)	C5—C4—C3—C2	0.8 (3)
C7—N1—C8—C9	−178.63 (14)	C3—C4—C5—C6	−0.8 (3)
C6—C1—C2—C3	0.3 (2)	C1—C6—C5—C4	0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.96	2.37	2.749 (2)	103
C2—H2···O1ⁱ	0.93	2.58	3.4356 (19)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₀ClNO
M_r	183.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.3391 (12), 6.5898 (10), 18.941 (3)
β (°)	91.192 (9)
V (Å³)	915.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.26 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.912, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	9758, 3003, 1869
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.736

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.136, 1.04
No. of reflections	3003
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.96	2.37	2.749 (2)	103.2
C2—H2···O1ⁱ	0.93	2.58	3.4356 (19)	154.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).

References

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