(RS)-N-[(4-Chloro­phen­yl)(phen­yl)­meth­yl]­formamide

Zhi-Hong Zou; Qi-Yuan Wang; Zhong-Shu Li

doi:10.1107/S1600536808024124

. 2008 Aug 6;64(Pt 9):o1698. doi: 10.1107/S1600536808024124

(RS)-N-[(4-Chlorophenyl)(phenyl)methyl]formamide

Zhi-Hong Zou ^a,^*, Qi-Yuan Wang ^a, Zhong-Shu Li ^b

PMCID: PMC2960489 PMID: 21201687

Abstract

The racemic title compound, C₁₄H₁₂ClNO, contains two molecules in the asymmetric unit. The dihedral angles between the phenyl and benzene rings are 84.03 (15) and 83.92 (13)°. The crystal structure involves intermolecular N—H⋯O, C—H⋯Cl and C—H⋯O hydrogen bonds, linking molecules into layers parallel to the (100) plane.

Related literature

For related literature, see: Pflum et al. (2002 ▶); Wang et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO
M _r = 245.70
Monoclinic,
a = 16.830 (4) Å
b = 9.6318 (12) Å
c = 16.683 (4) Å
β = 111.538 (12)°
V = 2515.6 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.20 mm

Data collection

CCD area-detector diffractometerRigaku Scxmini
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.852, T _max = 0.940
20642 measured reflections
4421 independent reflections
2499 reflections with I > 2σ(I)
R _int = 0.079

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.202
S = 1.06
4421 reflections
307 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024124/rz2236sup1.cif

e-64-o1698-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024124/rz2236Isup2.hkl

e-64-o1698-Isup2.hkl^{(216.6KB, hkl)}

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	2.02	2.877 (4)	174
N2—H2A⋯O1ⁱⁱ	0.86	2.16	2.901 (4)	144
C18—H18A⋯O2ⁱⁱⁱ	0.93	2.54	3.368 (5)	148
C20—H20A⋯Cl2	0.93	2.82	3.633 (4)	146

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

Acknowledgments

The authors thank Professor Sun Bai-Wang of Southeast University for his help.

supplementary crystallographic information

Comment

As part of our ongoing investigations on the asymmetric synthesis, the title compound, C₁₄H₁₂ClNO, has been obtained as a racemic mixture and structurally characterized. The compound is the key intermediate for the synthesis of levocetirizine dihydrochloride (Pflum et al., 2002; Wang et al., 2007), a high effective non-sedating H₁ receptor antagonist for the treatment of allergic diseases (Wang et al., 2005). The asymmetric unit of the title compound (Fig. 1) contains two molecules. The dihedral angles formed by planes of the phenyl and benzene rings are 84.03 (15) and 83.92 (13)°. In the crystal structure (Fig. 2), intermolecular N—H···O, C—H···Cl and C—H···O hydrogen bonds (Table 1) link molecules into layers parallel to the (100) plane.

Experimental

All chemicals used (reagent grade) were commercially available. A mixture of (4-chlorophenyl)phenylmethanone (21.67 g) and formamide (18.02 g) was stirred at 180°C for 20 h. The mixture was cooled to room temperature, and the resulting precipitate was filtered off, washed with water and dried. Colourless crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a 60% aqueous ethanol solution.