2-(4-Chloro­phen­yl)imidazo[1,2-a]pyridine-3-carbaldehyde

Yun-Hui Li; Wen-Yu Liu; Yang Gao; Yu-Peng Wang

doi:10.1107/S1600536809048302

. 2009 Nov 25;65(Pt 12):o3192. doi: 10.1107/S1600536809048302

2-(4-Chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde

Yun-Hui Li ^a,^*, Wen-Yu Liu ^a, Yang Gao ^b, Yu-Peng Wang ^a

PMCID: PMC2971907 PMID: 21578903

Abstract

The asymmetric unit of the title compound, C₁₄H₉ClN₂O, contains two molecules with dihedral angles of 33.52 (11) and 34.58 (11)° between their benzene rings and imidazole ring systems. In the crystal, C—H⋯N and C—H⋯O interactions are observed. The crystal examined was found to be a racemic twin.

Related literature

For the synthesis, see: Burkholder et al. (2001 ▶). graphic file with name e-65-o3192-scheme1.jpg

Experimental

Crystal data

C₁₄H₉ClN₂O
M _r = 256.68
Orthorhombic,
a = 21.3367 (13) Å
b = 7.2391 (4) Å
c = 15.1748 (10) Å
V = 2343.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.35 × 0.29 × 0.28 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.870, T _max = 0.894
12428 measured reflections
4198 independent reflections
3564 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.089
S = 1.03
4198 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), 1800 Friedel pairs
Flack parameter: 0.40 (5)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048302/hb5204sup1.cif

e-65-o3192-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048302/hb5204Isup2.hkl

e-65-o3192-Isup2.hkl^{(205.7KB, 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
C11—H11⋯O2ⁱ	0.93	2.54	3.442 (3)	163
C12—H12⋯N4ⁱⁱ	0.93	2.59	3.518 (4)	172

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

Acknowledgments

The authors thank Changchun University of Science and Technology for supporting this work.

supplementary crystallographic information

Experimental

To a solution of 2.0 mmol 2-(4-chlorophenyl)H-imidazo[1,2-a]pyridine (Burkholder et al., 2001) in DMF (10 ml) was added phosphoryl trichloride (2.2 mmol) in one portion at room temperature under stirring. The mixture was heated to 353 K and stirred for 5.0 h. After the intermediate was consumed (monitored by TLC), the reaction mixture was extracted, filtered and concentrated in vacuo. The pure product was obtained through silica gel chromatography, and yellow blocks of (I) were obtained by slow evaporation of an ethyl acetate/petroleum ether (1:1) solution at room temperature.