11H-Indeno­[1,2-b]quinoxalin-11-one

Raza Murad Ghalib; Rokiah Hashim; Othman Sulaiman; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536810019252

. 2010 May 29;66(Pt 6):o1494. doi: 10.1107/S1600536810019252

11H-Indeno[1,2-b]quinoxalin-11-one

Raza Murad Ghalib ^a, Rokiah Hashim ^a, Othman Sulaiman ^a, Madhukar Hemamalini ^b, Hoong-Kun Fun ^b,^*,^‡

PMCID: PMC2979415 PMID: 21579556

Abstract

In the title compound, C₁₅H₈N₂O, the fused ring system is approximately planar, with a maximum deviation of 0.039 (1) Å. In the crystal, weak intermolecular C—H⋯O interactions help to establish the packing.

Related literature

For applications of and background to indenoquinoxaline, see: Gazit et al. (1996 ▶); Sehlstedt et al. (1998 ▶). For a related structure, see: Leslie et al. (1993 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₈N₂O
M _r = 232.23
Orthorhombic,
a = 23.688 (3) Å
b = 3.7862 (5) Å
c = 11.5730 (16) Å
V = 1038.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.65 × 0.17 × 0.09 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.940, T _max = 0.991
8012 measured reflections
2004 independent reflections
1879 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.05
2004 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019252/hb5459sup1.cif

e-66-o1494-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019252/hb5459Isup2.hkl

e-66-o1494-Isup2.hkl^{(96.6KB, hkl)}

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
C3—H3A⋯O1ⁱ	0.96 (2)	2.55 (2)	3.401 (2)	148.3 (19)
C9—H9A⋯O1ⁱⁱ	0.97 (3)	2.49 (3)	3.2458 (18)	134.0 (18)

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

Acknowledgments

RMG, RH and OS thank Universiti Sains Malaysia (USM) for the University Grant 1001/PTEKIND/8140152. MH and HKF thank the Malaysian Government and USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. RMG and MH also thank USM for post-doctoral research fellowships.

supplementary crystallographic information

Comment

Indenoquinoxaline derivatives are important classes of nitrogen containing heterocycles and they constitute useful intermediates in organic synthesis (Gazit et al., 1996). They have been reported for their applications in dyes and have also been used as building blocks for the synthesis of organic semiconductors. More interestingly, research has revealed that these compounds exhibit diverse medicinal functions such as antimetabolism and antitubercular properties (Sehlstedt et al., 1998). In view of the biological importance of indenoquinoxalines, we report here the crystal structure of the title compound, (I).

The molecule of indeno[1,2-b]quinoxalin-11-one (Fig. 1) is approximately planar with maximum deviation of 0.039 (1) Å for atom C14. It contains three ring systems, viz., indene (C7–C15), pyrazine (N1/N2/C6–C7/C1/C15) and benzene (C1–C6). The C–N bond distances and C—N—C angles are C15—N1 = 1.3070 (17) Å, C1—N1 = 1.3793 (18) Å, C7—N2 = 1.3142 (17) Å, C6—N2 = 1.3800 (17) Å, C15—N1—C1 = 113.99 (12)° and C7—N2—C6 = 114.00 (12)°. These values agree with those reported in the related structure of 11H-indeno[1,2-b]quinoxalin-11-ones (Leslie et al., 1993). The pyrazine (N1/N2/C6–C7/C1/C15) ring makes dihedral angles of 0.48 (5)° and 1.34 (6)° with the indene (C7–C15) ring and the benzene (C1–C6) ring, respectively. The dihedral angle between the indene (C7–C15) ring and benzene (C1–C6) ring is 0.88 (6)°.

In the crystal structure, molecules are linked by weak intermolecular C3—H3A···O1 and C9—H9A···O1 hydrogen bonds (Table 1) interactions which help to stabilize the crystal structure.

Experimental

The title compound, has been synthesized by two routes: a mixture of ninhydrin (1.78 g) and o-phenylenediamine (1.08 g) in molar ratio 1:1 were [a] stirred in distilled water for 15 minutes and [b] refluxed in THF for 1 hour in presence of HCl. Both these mixtures were separately dried on rota-vapor at low pressure and then crystallized from chloroform-n-hexane (1:1) to give yellowish needles of (I).