Methyl 11-hy­droxy-9-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.01,8.02,6.012,17]octa­deca-12(17),13,15-triene-8-carboxyl­ate

Sivasubramanian Suhitha; Thothadri Srinivasan; Raju Rajesh; Raghavachary Raghunathan; Devadasan Velmurugan

doi:10.1107/S1600536813004789

. 2013 Feb 23;69(Pt 3):o438–o439. doi: 10.1107/S1600536813004789

Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0^1,8.0^2,6.0^12,17]octadeca-12(17),13,15-triene-8-carboxylate

Sivasubramanian Suhitha ^a, Thothadri Srinivasan ^a, Raju Rajesh ^b, Raghavachary Raghunathan ^b, Devadasan Velmurugan ^a,^*

PMCID: PMC3588541 PMID: 23476608

Abstract

In the title compound, C₃₄H₃₂N₂O₇, the furan ring adopts a twist conformation and both the pyrrolidine rings adopt envelope conformations with O and C as flap atoms. The β-lactam ring makes a dihedral angles of 80.20 (10)° with the furan ring, of 75.55 (10)° with the pyrrolidine ring, of 12.26 (10)° with the methoxyphenyl ring and of 73.77 (13)° with the phenyl ring. The O atom attached to the β-lactam ring deviates by 0.0385 (13) Å from the ring plane. The molecular conformation is stabilized by intramolecular O—H⋯N and C—H⋯O hydrogen bonds. The packing of the crystal is stabilized by intermolecular C—H⋯O hydrogen bonds, which form a chain running along the b axis.

Related literature

For general background to β-lactams, see: Banik & Becker (2000 ▶); Brakhage (1998 ▶). For a related structure, see: Sundaramoorthy et al. (2012 ▶).

Experimental

Crystal data

C₃₄H₃₂N₂O₇
M _r = 580.62
Monoclinic,
a = 10.9030 (5) Å
b = 11.8792 (5) Å
c = 22.4457 (10) Å
β = 93.963 (3)°
V = 2900.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.973, T _max = 0.982
28525 measured reflections
7293 independent reflections
4952 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.127
S = 1.02
7293 reflections
394 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(30.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004789/bt6889sup1.cif

e-69-0o438-sup1.cif^{(30.1KB, cif)}

Click here for additional data file.^{(349.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004789/bt6889Isup2.hkl

e-69-0o438-Isup2.hkl^{(349.7KB, hkl)}

Click here for additional data file.^{(11.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813004789/bt6889Isup3.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
O4—H4A⋯N2	0.91 (2)	1.95 (2)	2.6120 (16)	127.8 (19)
C6—H6⋯O1	0.93	2.51	3.122 (2)	124
C8—H8⋯O1ⁱ	0.98	2.52	3.4047 (19)	151
C28—H28A⋯O4ⁱⁱ	0.97	2.58	3.5069 (19)	161

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

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship and SS thanks the UGC for a meritorious fellowship.

supplementary crystallographic information

Comment

The role of β-lactam antibiotics is well known (Banik & Becker, 2000). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). In view of potential applications, the crystal structure determination of the titled β-lactam derivative was carried out. In the title compound (Fig. 1), the β lactam ring makes a dihedral angle of 80.20 (10)° with the furan ring (C17/C18/C19/C27/O3) and a dihedral angle of 75.55 (10)° with the pyrrolidine ring (C18/C19/C28/C29/N2). The β lactam ring makes a dihedral angle of 12.26 (10)° with the methoxy phenyl ring and a dihedral angle of 73.77 (13)° with unsubstituted phenyl ring.

Both the pyrrolidine rings adopt an envelope conformation and the furan ring adopts a twist conformation. The furan ring makes a dihedral angle of 81.29 (8)° with the pyrrolidine ring, a dihedral angle of 72.61 (9)° with the other pyrrolidine ring(N2/C29/C30/C31/C32). The furan ring makes a dihedral angle of 72.26 (8)° with the cyclopentane ring(C19/C20/C21/C26/C27) system. The oxygen atom (O1) attached with the β lactam ring deviates by 0.0385 (13)Å from the ring plane. The hydroxyl oxygen atom (O4) attached with the furan ring deviates by -0.6644 (11)Å from the ring plane. The oxygen atom (O5) attached to the cyclopentane ring deviates by 0.2042 (13)Å from the ring plane. The molecular conformation is stabilized by an intramolecular O-H···N and C-H···O hydrogen bonds. The packing of the crystal is stabilized by intermolecular C—H···O hydrogen bonds (Fig. 2).

Experimental

A mixture of methyl 2-(hydroxy(1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl) methyl)acrylate (1.0 equiv.), ninhydrin (1.1 equiv.) and proline (1.1 equiv.) was refluxed in methanol. Completion of the reaction was evidenced by TLC analysis. After completion of the reaction the solvent was evaporated under reduced pressure. The reaction mixture was dissolved in dichloromethane and with water followed by brine solution. The organic layer was separated and evaporated under reduced pressure. The crude mixture was purified by column chromatography using ethyl acetate and hexane as eluent (3: 7). The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 48 hours resulting in the formation of single crystals.