(2E)-2-Benzyl­idene-9-phenyl-3,4-di­hydro­acridin-1(2H)-one

T Vinuchakkaravarthy; M Sankaran; P S Mohan; D Velmurugan

doi:10.1107/S1600536814015943

. 2014 Jul 17;70(Pt 8):o870. doi: 10.1107/S1600536814015943

(2E)-2-Benzylidene-9-phenyl-3,4-dihydroacridin-1(2H)-one

T Vinuchakkaravarthy ^a, M Sankaran ^b, P S Mohan ^b, D Velmurugan ^a,^*

PMCID: PMC4158519 PMID: 25249917

Abstract

In the title compound, C₂₆H₁₉NO, the plane of the aromatic heterocycle makes a dihedral angle of 75.22 (4)° with that of the attached phenyl ring. In the crystal, molecules are connected by C—H⋯O interactions, generating R ₂ ²(12) dimers. These dimers are further connected by C—H⋯π interactions, linking the molecules into chains running along the a-axis direction.

Keywords: crystal structure

Related literature

For background to acridines, see: Kumar et al. (2012 ▶). For the biological activity of acridine derivatives, see: Pigatto et al. (2011 ▶); Das et al. (2011 ▶); Kumar et al. (2012 ▶); Prommier et al. (2006 ▶) Denny et al. (1982 ▶); Baguley & Ferguson (1998 ▶). For the synthesis of acridines, see: Tomar et al. (2010 ▶). For related structures, see: Buckleton & Waters (1984 ▶); Chantrapromma et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₁₉NO
M _r = 361.42
Monoclinic,
a = 9.2222 (3) Å
b = 10.7555 (4) Å
c = 19.4962 (5) Å
β = 95.503 (2)°
V = 1924.90 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.662, T _max = 0.746
18382 measured reflections
4776 independent reflections
3205 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.131
S = 1.00
4776 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 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

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814015943/bt6954sup1.cif

e-70-0o870-sup1.cif^{(28.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015943/bt6954Isup2.hkl

e-70-0o870-Isup2.hkl^{(229.2KB, hkl)}

Click here for additional data file.^{(7.3KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015943/bt6954Isup3.cml

CCDC reference: 1012814

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1ⁱ	0.97	2.58	3.2700 (18)	128
C26—H26⋯Cg1ⁱⁱ	0.93	2.71	3.577 (18)	156

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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. TV and DV also thank the UGC (SAP–CAS) for the facilities to the department.

supplementary crystallographic information

S1. Comment

Acridine is structurally related to anthracene with one of the central CH group replaced by nitrogen. Amsacrine which is an acridine derivative is clinically used for the treatment of cancer (Denny et al., 1982; Baguley & Ferguson, 1998). The strong activity of acridine derivatives is due to their ability to intercalate into DNA base pairs and leading to cell cycle arrest and apoptosis (Prommier et al., 2006).

The phenyl (C21—C26) and benzyl (C14—C20) rings deviate from the plane of the acridine system by 72.48 (6) ° and 49.24 (6) °, respectively. The crystal packing is stabilized by intermolecular C—H···O (C10—H10B···O1) interactions generating a R²₂(12) ring motif (Bernstein et al., 1995). These dimers are further connected by C—H···π (C26—H26···Cg1) interactions generating chains running along the a-axis.

S2. Experimental

A 1:2 molar mixture of 9-phenyl-3,4-dihydroacridin-1(2H)-one was treated with aromatic aldehydes in the presence of NaOH and allowed to stir at room temperature for 5–7 h. After completion of the reaction as inferred by the TLC, the mixture was poured into 200 g of crushed ice and neutralized with dil HCl. The precipitate thus formed after adding into crushed ice was filtered off and the residue subjected to column chromatography using petroleum ether: ethyl acetate mixture (3:1) v/v as eluent and compound obtained as a pale yellow solid.