Crystal structure of ethyl 2-(2-{1-[N-(4-bromo­phen­yl)-2-oxo-2-phenyl­acetamido]-2-tert-butyl­amino-2-oxo­ethyl}-1H-pyrrol-1-yl)acetate

Tetsuji Moriguchi; Venkataprasad Jalli; Suvratha Krishnamurthy; Akihiko Tsuge; Kenji Yoza

doi:10.1107/S2056989015023592

. 2015 Dec 12;71(Pt 12):o1049–o1050. doi: 10.1107/S2056989015023592

Crystal structure of ethyl 2-(2-{1-[N-(4-bromophenyl)-2-oxo-2-phenylacetamido]-2-tert-butylamino-2-oxoethyl}-1H-pyrrol-1-yl)acetate

Tetsuji Moriguchi ^a,^*, Venkataprasad Jalli ^a, Suvratha Krishnamurthy ^a, Akihiko Tsuge ^a, Kenji Yoza ^b

PMCID: PMC4719973 PMID: 26870492

Abstract

In the title compound, C₂₈H₃₀BrN₃O₅, there is an intramolecular N—H⋯O hydrogen bond and an intramolecular C—H⋯O hydrogen bond, both forming S(9) ring motifs. The planes of the 4-bromophenyl ring and the phenyl ring are inclined to that of the pyrrole ring by 48.05 (12) and 77.45 (14)°, respectively, and to one another by 56.25 (12)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds and C—H⋯π interactions, forming slabs parallel to (10-1).

Keywords: crystal structure, pyrrole derivative, hydrogen bonding, C—H⋯π interactions

Related literature

For examples of the biological and pharmacological properties of pyrrole derivatives, see: Daidone et al. (1990 ▸); Davis et al. (2008 ▸); Kaiser & Glenn (1972 ▸); Meshram et al. (2010 ▸).

Experimental

Crystal data

C₂₈H₃₀BrN₃O₅
M _r = 568.46
Monoclinic,
a = 11.656 (3) Å
b = 17.997 (5) Å
c = 13.463 (4) Å
β = 97.351 (3)°
V = 2801.0 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 120 K
0.45 × 0.45 × 0.30 mm

Data collection

Bruker APEXII KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.600, T _max = 0.636
25937 measured reflections
4924 independent reflections
3479 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.086
S = 1.35
4924 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015023592/su5258sup1.cif

e-71-o1049-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023592/su5258Isup2.hkl

e-71-o1049-Isup2.hkl^{(241.2KB, hkl)}

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup3.pdf

e-71-o1049-Isup3.pdf^{(298.6KB, pdf)}

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup4.pdf

e-71-o1049-Isup4.pdf^{(296.3KB, pdf)}

Click here for additional data file.^{(9.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup5.cml

Click here for additional data file.^{(1.8MB, tif)}

. DOI: 10.1107/S2056989015023592/su5258fig1.tif

Molecular structure and atom labelling for the title compound, with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(1.8MB, tif)}

b . DOI: 10.1107/S2056989015023592/su5258fig2.tif

Crystal packing of the title compound, viewed along the b axis, with the hydrogen bonds shown as dashed lines (see Table 1). H atoms not involved in these reactions have been omitted for clarity.

Click here for additional data file.^{(16.3KB, tif)}

. DOI: 10.1107/S2056989015023592/su5258fig3.tif

Reaction scheme for the synthesis of the title compound.

CCDC reference: 1441330

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the N1/C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1	0.86	2.13	2.970 (3)	164
C14—H24⋯O3	0.93	2.57	3.199 (3)	148
C8—H8B⋯O4ⁱ	0.96	2.55	3.432 (3)	154
C17—H17⋯O3ⁱⁱ	0.93	2.34	3.269 (3)	176
C7—H7A⋯Cg1ⁱⁱⁱ	0.97	2.86	3.697 (3)	151

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

Acknowledgments

We are grateful to the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA), for the X-ray analysis.

supplementary crystallographic information

S1. Comments

Pyrrole and its derivatives are important classes of heterocyclic compounds because of their important biological and pharmacological properties. They have been shown to have important biological properties, such as antibacterial (Daidone et al., 1990), anti inflammatory (Kaiser & Glenn, 1972), antitumor (Meshram et al., 2010), and immune suppressant activities (Davis et al., 2008). Pyrrole analogs are important components in naturally occurring bio molecules such as heme, chlorophyll, vitamin B12 and pyrrole alkaloids isolated from marine sources. Highly functionalized pyrroles are found in drug molecules such as Atorvastatin, Ketorolac and Sunitinib. Thus, the elucidation of the crystal structures of pyrrole derivatives has attracted much attention. Here, we report on the crystal structure of the racemic title compound, synthesized by a four component one pot reaction, involving pyrrole-1-acetic acid-2-formyl ethyl ester, 4-bromo aniline, phenyl glyoxylic acid and tert-butyl isocyanide.

In the title compound, Fig. 1, there is an intramolecular N—H···O hydrogen bonding forming an S(9) ring motif. There is also intramolecular C—H···O hydrogen bonding which also forms an S(9) ring motif. The 4-bromophenyl ring and the phenyl ring are inclined to the pyrrole ring by 48.05 (12) and 77.45 (14) °, respectively, and to one another by 56.25 (12) °.

In the crystal, molecules are linked via C—H···O hydrogen bonds and C—H···π interactions forming slabs parallel to (101); see Table 1 and Fig. 2.

S2. Synthesis and crystallization

The reaction scheme for the synthesis of the title compound is illustrated in Fig. 3. A mixture of pyrrole-1-acetic acid-2-formyl ethylester (2 mmol), 4-bromoaniline (2 mmol), phenylglyoxylic acid (2.2 mmol) and τ-butyl-isocyanide (2 mmol) were taken in 10 ml of MeOH and stirred at room temperature for 18 h. The volatiles were removed under reduced pressure and the pure product was isolated by column chromatography, using 30% EtOAc/Hexane, as a white coloured solid. Colourless prismatic crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature. The compound crystalized in the racemic form. Spectroscopic data: LCMS: MH⁺, 568. IR (ν_max, KBr, cm⁻¹) 3144, 1740, 1730, 1725; ¹H NMR (500 MHz, CDCl₃, δ_H) 7.99 (2 H, d), 7.57 (1 H, m), 7.44–7.47 (3 H, m), 7.14 (2 H, m), 6.8 (1 H, s), 6.61 (1 H, m), 6.14 (1 H, d), 6.09 (1 H, s), 5.99 (1 H, m), 5.65 (1 H, m), 4.74 (2 H, s), 4.29 (2 H, q), 1.36 (9 H, s), 1.33 (3 H, t).

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were included in calculated positions and treated as riding atoms: N—H = 0.86 Å, C—H = 0.93 − 0.98 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(N,C) for other H atoms.