4-Chloro-N-methyl­benzamide

Juan Yuan; Yan-Ju Liu

doi:10.1107/S1600536812008641

. 2012 Mar 3;68(Pt 4):o937. doi: 10.1107/S1600536812008641

4-Chloro-N-methylbenzamide

Juan Yuan ^a, Yan-Ju Liu ^a,^*

PMCID: PMC3343919 PMID: 22590000

Abstract

There are two molecules in the asymmetric unit of the title compound, C₈H₈ClNO, which are linked in the crystal structure via N—H⋯O hydrogen bonds into chains along the b axis. C—H⋯O contacts also occur. The benzene ring makes dihedral angles of 5.9 (1) and 16.7 (1)°with the attached amide group in the two independent molecules.

Related literature

For applications of the title compound and background to the synthesis, see: Lee et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₈ClNO
M _r = 169.61
Triclinic,
a = 3.9420 (8) Å
b = 9.2250 (18) Å
c = 21.864 (4) Å
α = 96.46 (3)°
β = 90.34 (3)°
γ = 90.99 (3)°
V = 789.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.921, T _max = 0.959
3079 measured reflections
2887 independent reflections
1633 reflections with I > 2σ(I)
R _int = 0.047
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.188
S = 1.00
2887 reflections
199 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008641/bq2339sup1.cif

e-68-0o937-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008641/bq2339Isup2.hkl

e-68-0o937-Isup2.hkl^{(141.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008641/bq2339Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.07	2.876 (4)	157
N2—H2B⋯O1ⁱⁱ	0.86	2.06	2.887 (4)	160
C5—H5A⋯O2ⁱ	0.93	2.53	3.417 (5)	159
C9—H9A⋯O1ⁱⁱ	0.93	2.60	3.379 (5)	142

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This study was supported by the Science and Technology Department of Henan Province (102102310321) and the Doctoral Research Fund of Henan Chinese Medicine (BSJJ2009–38). The authors thank the Center of Testing and Analysis, Nanjing University for the data collection.

supplementary crystallographic information

Comment

Benzamide derivatives exhibit interesting biological activities such as antibacterial and antifungal effects (Lee et al., 2009). We report here the crystal structure of the title compound 4-chloro-N-methylbenzamide, (I).

The molecular structure of (I) is shown in Fig. 1. The title compound was connected together via N—H···O intermolecular hydrogen bonds (Table 1), supported by a C—H···O contact, forming chains along b axis direction (Figure 2.).

The asymmetric unit contains two title molecules of 4-chloro-N-methylbenzamide. The rings of these molecules are planar with r.m.s. deviation of 0.0048 Å and 0.0034 Å. The dihedral angles of the planes A(C1—C6), B(C7/O1/N1/H1A), C(C9—C14), D(C15/O2/N2/H2B) are: A/B = 5.9 (1)°, C/D = 16.7 (1)° and A/C = 16.77 (16) °.

Experimental

The title compound, (I) was prepared by a method reported in literature (Lee et al., 2009). The crystals were obtained by dissolving (I) (0.1 g) in methanol (30 ml) and evaporating the solvent slowly at room temperature for about 8 d.