Crystal structure of 2-[4-(4-chloro­phen­yl)-1-(4-meth­oxy­phen­yl)-2-oxoazetidin-3-yl]benzo[de]iso­quinoline-1,3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik; Mehmet Akkurt; Aliasghar Jarrahpour; Javad Ameri Rad; Ömer Çelik

doi:10.1107/S2056989015001425

. 2015 Jan 28;71(Pt 2):o129–o130. doi: 10.1107/S2056989015001425

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik ^a, Mehmet Akkurt ^b,^*, Aliasghar Jarrahpour ^c, Javad Ameri Rad ^c, Ömer Çelik ^d,^e

PMCID: PMC4384601 PMID: 25878867

Abstract

In the title solvated compound, C₂₈H₁₉N₂O₄·C₂H₆OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C—H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C—H⋯O hydrogen bonds, C—H⋯π interactions and aromatic π–π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Keywords: crystal structure; β-lactam ring; 1H-benzo[de]isoquinoline-1,3(2H)-dione group; disorder; azetidin-2-ones

Related literature

For general background to β-lactams, see: Alcaide & Almendros (2004 ▸); Alcala et al. (2011 ▸); Li et al. (2011 ▸); Long & Turos (2002 ▸); MacIntyre et al. (2010 ▸); Rogers & Kelly (1999 ▸); Sawa et al. (2006 ▸); Southgate (1994 ▸); Zhang & Zhou (2011 ▸); Zhang et al. (2011 ▸). For related structures, see: Atioğlu et al. (2014 ▸); Butcher et al. (2011 ▸); Jarrahpour et al. (2012 ▸); Zarei (2013 ▸).

Experimental

Crystal data

C₂₈H₁₉ClN₂O₄·C₂H₆OS
M _r = 561.03
Triclinic,
a = 7.9925 (3) Å
b = 12.1761 (5) Å
c = 14.2313 (6) Å
α = 93.549 (2)°
β = 95.520 (2)°
γ = 101.602 (2)°
V = 1345.67 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.45 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
29975 measured reflections
7737 independent reflections
5777 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.191
S = 1.05
7737 reflections
359 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001425/hb7354sup1.cif

e-71-0o129-sup1.cif^{(37.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001425/hb7354Isup2.hkl

e-71-0o129-Isup2.hkl^{(423.8KB, hkl)}

Click here for additional data file.^{(9.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015001425/hb7354Isup3.cml

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S2056989015001425/hb7354fig1.tif

Perspective view of the molecular structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 30% probability level. Only the major component of the disordered solvent molecule is displayed.

Click here for additional data file.^{(3.2MB, tif)}

a . DOI: 10.1107/S2056989015001425/hb7354fig2.tif

The hydrogen bonding and molecular packing of the title compound along a axis. Only the major component of the disordered solvent molecule is displayed.

Click here for additional data file.^{(2.5MB, tif)}

c . DOI: 10.1107/S2056989015001425/hb7354fig3.tif

The hydrogen bonding and molecular packing of the title compound along c axis. Only the major component of the disordered solvent molecule is displayed.

CCDC reference: 1044874

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

Table 1. Hydrogen-bond geometry (, ).

Cg4 is the centroid of the C11C16 benzene ring.

DHA	DH	HA	D A	DHA
C5H5O1	0.93	2.57	3.169(3)	122
C21H21O1ⁱ	0.93	2.52	3.344(2)	148
C25H25O4ⁱⁱ	0.93	2.46	3.221(2)	139
C30AH30A Cg4ⁱⁱⁱ	0.96	2.88	3.818(10)	167

Open in a new tab

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

Acknowledgments

The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and JAR thank the Shiraz University Research Council for financial support (grant No. 93-GR–SC-23).

supplementary crystallographic information

S1. Comment

Even more than 70 years after the discovery of penicillin, β-lactam antibiotics remain as one of the most important contributions of science to humanity (Southgate, 1994) and the β-lactam antibiotics have served as a powerful line of defense against bacterial infections (Long, et al., 2002). They have also been used as synthons for the synthesis of various natural and unnatural products (Alcaide & Almendros, 2004). On the other hand, cyclic imides have received special attraction due to their widely potential pharmaceutical applications (Zhang & Zhou, 2011). Isoquinolindione (naphthalimide) derivatives are cyclic imides to be of interest due to their useful photophysical and biological properties that offer promise for medical applications as free radical scavengers (Zhang, et al., 2011), potential photoredox anticancer agents (MacIntyre, et al., 2010), fluorescent labels (Sawa, et al., 2006), photosensitizers (Rogers & Kelly, 1999) and imaging agents (Alcala et al., 2011). Many of these properties are related to 1,8- naphthalimides planar shape and optimal size that makes them efficient DNA intercalating agents with high antitumor activity (Li et al., 2011; Zarei, 2013).

In the title compound (Fig. 1), the β-lactam ring (N1/C1–C3) is nearly planar [r.m.s. deviation = 0.002 Å]. It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy and choloro phenyl rings (C4–C9 and C11–C16) and the ring plane (N2/C17–C28) of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group which is nearly planar [max. deviations = -0.089 (1) Å for N2 and 0.044 (2) Å for C24], respectively.

All bond lengths and bond angles are normal and comparable with those reported for related compounds (Butcher et al., 2011; Atioğlu et al., 2014; Jarrahpour et al., 2012).

Molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal, molecules are linked by intermolecular C—H···O hydrogen bonds, forming three dimensional network (Table 1, Figs. 2 & 3).

Furthermore, one weak C—H···π interaction (Table 1) and π-π stacking interactions [Cg2···Cg6 (2 - x,1 - y,-z) = 3.6166 (10) Å and Cg5···Cg6(2 - x,1 - y,-z) = 3.7159 (10) Å; where Cg2, Cg5 and Cg6 are centroids of the N2/C17/C18/C23/C24/C28 central pyridine ring and the C18–C23 and C22—C27 benzene rings of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group, respectively] also partially take part in the stabilization of the structure.

S2. Experimental

4-Chlorophenyl-N-(4-methoxyphenyl)methanimine (1 mmol), triethylamine (5 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid (1.50 mmol) and tosyl chloride (1.50 mmol) were added to anhydrous CH₂Cl₂ (5 ml) and the mixture was stirred at room temperature for 24 h. The mixture was washed with HCl 1 N (2×20 ml), saturated aqueous NaHCO₃ solution (50 ml) and brine (20 ml). The organic layer was dried (Na₂SO₄) and the solvent was removed to give the product as a white solid·It was then purified by recrystallization from DMSO to afford colourless triclinic crystals (Yield 75%); Mp: 528–530 K; IR (KBr, cm^-1): 1774 (CO β-lactam),1704 (CO Naph), 1666 (CO Naph); ¹H-NMR (250 MHz, DMSO-d₆) δ 1.27 (CH₃ t, 3H, J = 6.75), 3.95 (CH₂ q, 2H, J = 6.75), 5.69 (CH β-lactam d, 1H, J = 2.75), 5.94 (CH β-lactam d, 1H, J = 2.75), 6.91 (aromat d, 2H, J = 9.00), 7.19 (aromat d, 2H, J = 9.00), 7.79–7.89 (ArH, m, 4H), 8.24 (aromat d, 2H, J = 9.00), 8.43–8.50 (ArH, m, 4H); ¹³C-NMR (62 MHz, DMSO-d₆) δ 163.22 (CO β-lactam), 162.13 (CO Naph), 155.04, 147.47, 144.82, 134.88, 131.22, 131.17, 130.50, 128.10, 127.43, 127.30, 123.95, 121.54, 118.29, 115.04, (aromatic carbons), 63.41 (C β-lactam), 63.19 (C β-lactam), 58.08 (CH₂—O), 14.56 (CH₃); GC—MS m/z = 507 [M+].