2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon­yloxy]eth­yl}anilino)ethyl 1H-pyrrole-2-carboxyl­ate

Ying Yan; Guilong Zhang; Zhenming Yin

doi:10.1107/S1600536811056170

. 2012 Jan 14;68(Pt 2):o378. doi: 10.1107/S1600536811056170

2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbonyloxy]ethyl}anilino)ethyl 1H-pyrrole-2-carboxylate

Ying Yan ^a, Guilong Zhang ^b, Zhenming Yin ^a,^*

PMCID: PMC3275056 PMID: 22347001

Abstract

In the title molecule, C₂₀H₂₀ClN₃O₄, both the pyrrole N—H groups adopt a syn conformation with respect to the carbonyl groups. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into layers parallel to (102).

Related literature

For the crystal structures of related pyrrole-2-carboxylate derivatives, see: Sessler et al. (2003 ▶); Yin & Li (2006 ▶); Maeda et al. (2007 ▶); Cui et al. (2009 ▶).

Experimental

Crystal data

C₂₀H₂₀ClN₃O₄
M _r = 401.84
Monoclinic,
a = 19.972 (2) Å
b = 4.7426 (5) Å
c = 20.613 (2) Å
β = 95.815 (2)°
V = 1942.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.488, T _max = 1.000
9198 measured reflections
3438 independent reflections
1763 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.106
S = 1.01
3438 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811056170/cv5220sup1.cif

e-68-0o378-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056170/cv5220Isup2.hkl

e-68-0o378-Isup2.hkl^{(168.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811056170/cv5220Isup3.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—H1⋯O1ⁱ	0.86	2.07	2.893 (3)	160
N3—H3⋯O4ⁱⁱ	0.86	2.07	2.891 (3)	158

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

Acknowledgments

We sincerely thank the Natural Science Foundation of China for financial support from the (NSFC grant Nos. 21172174 and 20702038).

supplementary crystallographic information

Comment

The use of 2-carbonyl-functionalized pyrrole moieties as building blocks to create hydrogen bonded self-assembled aggregates has received some attention recently (Sessler et al., 2003; Yin et al. 2006; Maeda et al. 2007). In continuation of our study of the solid state self-assemblies of some pyrrole-2-carboxylate compounds (Cui et al. 2009), we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), both the pyrrole NH groups adopt syn conformation with respect to the carbonyl groups. The molecules of the title compound self-assemble into one-dimensional tape through helical N—H···O hydrogen bonds (Table 1). Further, intermolecular N—H···O hydrogen bonds (Table 1) link these tapes into layers parallel to (102) plane. The hydrogen bonding motif in the crystal of (I) is different from that reported for N,N-di[2- (1H-pyrrole-2-carbonyloxy)ethyl]-aniline (Cui et al., 2009). Apparently, the chloro group has great influence on the crystal packing.

Experimental

N,N-Di(2-hydroxyethyl)-4-chloroaniline (0.215 g), 2-(trichloroacetyl)-1H-pyrrole(0.59 g) and triethylamine (1 mL) were added to acetonitrile (15 ml), and the mixture was refluxed for 10 h. The solution was then evaporated under reduced pressure and the residue was purified by column chromatography on silica gel with ethyl acetate-petroleum ether (1:4 v/v), affording the title compound.