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

In the title compound, C(15)H(8)N(2)O, the fused ring system is approximately planar, with a maximum deviation of 0.039 (1) Å. In the crystal, weak inter-molecular C-H⋯O inter-actions 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 = 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

Δρmax = 0.35 e Å−3

Δρmin = −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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H8N2O	F(000) = 480
Mr = 232.23	Dx = 1.486 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3067 reflections
a = 23.688 (3) Å	θ = 3.4–32.7°
b = 3.7862 (5) Å	µ = 0.10 mm−1
c = 11.5730 (16) Å	T = 100 K
V = 1038.0 (2) Å3	Needle, yellow
Z = 4	0.65 × 0.17 × 0.09 mm

Bruker APEXII DUO CCD diffractometer	2004 independent reflections
Radiation source: fine-focus sealed tube	1879 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.9°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −34→35
Tmin = 0.940, Tmax = 0.991	k = −5→5
8012 measured reflections	l = −17→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0723P)2] where P = (Fo2 + 2Fc2)/3
2004 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.33655 (5)	0.7879 (3)	1.04339 (10)	0.0172 (2)
N1	0.42154 (5)	0.4986 (3)	0.87194 (11)	0.0133 (2)
N2	0.35873 (5)	0.1857 (3)	0.68337 (10)	0.0133 (2)
C1	0.44805 (5)	0.3540 (4)	0.77697 (12)	0.0124 (2)
C2	0.50791 (6)	0.3630 (4)	0.77183 (14)	0.0159 (2)
C3	0.53554 (6)	0.2296 (4)	0.67669 (15)	0.0181 (3)
C4	0.50483 (6)	0.0792 (4)	0.58433 (14)	0.0178 (3)
C5	0.44661 (6)	0.0648 (4)	0.58754 (13)	0.0161 (2)
C6	0.41693 (6)	0.2018 (3)	0.68361 (12)	0.0129 (2)
C7	0.33505 (5)	0.3278 (3)	0.77494 (12)	0.0113 (2)
C8	0.27433 (5)	0.3583 (3)	0.80211 (12)	0.0117 (2)
C9	0.22743 (6)	0.2529 (4)	0.73926 (13)	0.0141 (2)
C10	0.17415 (6)	0.3143 (4)	0.78798 (14)	0.0162 (3)
C11	0.16835 (6)	0.4757 (4)	0.89631 (14)	0.0166 (3)
C12	0.21568 (6)	0.5858 (4)	0.95898 (14)	0.0145 (2)
C13	0.26863 (5)	0.5257 (3)	0.91037 (13)	0.0120 (2)
C14	0.32527 (5)	0.6219 (3)	0.95612 (12)	0.0122 (2)
C15	0.36646 (6)	0.4822 (3)	0.86782 (12)	0.0116 (2)
H2A	0.5309 (9)	0.475 (6)	0.834 (3)	0.024 (6)*
H3A	0.5758 (10)	0.236 (6)	0.671 (2)	0.022 (5)*
H4A	0.5277 (11)	−0.002 (7)	0.519 (3)	0.033 (7)*
H5A	0.4213 (10)	−0.031 (6)	0.527 (3)	0.025 (6)*
H9A	0.2305 (9)	0.133 (6)	0.665 (2)	0.024 (6)*
H10A	0.1405 (11)	0.235 (6)	0.746 (2)	0.024 (6)*
H11A	0.1301 (12)	0.493 (7)	0.927 (2)	0.035 (7)*
H12A	0.2086 (14)	0.697 (8)	1.033 (3)	0.048 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0188 (4)	0.0209 (5)	0.0120 (5)	−0.0003 (4)	−0.0011 (4)	−0.0053 (4)
N1	0.0141 (5)	0.0137 (5)	0.0121 (5)	0.0003 (4)	−0.0006 (4)	−0.0002 (4)
N2	0.0165 (5)	0.0125 (5)	0.0108 (5)	0.0005 (4)	−0.0005 (4)	−0.0006 (4)
C1	0.0136 (5)	0.0118 (5)	0.0119 (5)	0.0001 (4)	−0.0002 (4)	0.0004 (4)
C2	0.0154 (5)	0.0150 (5)	0.0173 (6)	−0.0003 (5)	0.0013 (5)	0.0007 (5)
C3	0.0160 (5)	0.0164 (6)	0.0217 (7)	0.0021 (5)	0.0039 (5)	0.0026 (5)
C4	0.0197 (6)	0.0157 (6)	0.0181 (6)	0.0021 (5)	0.0063 (5)	0.0014 (5)
C5	0.0195 (6)	0.0137 (6)	0.0150 (6)	0.0015 (5)	0.0026 (5)	−0.0010 (4)
C6	0.0156 (5)	0.0117 (5)	0.0113 (6)	0.0004 (4)	0.0006 (5)	0.0002 (4)
C7	0.0132 (5)	0.0103 (5)	0.0103 (5)	0.0007 (4)	−0.0007 (4)	0.0002 (4)
C8	0.0133 (5)	0.0114 (5)	0.0106 (5)	0.0006 (4)	−0.0011 (4)	0.0001 (4)
C9	0.0149 (5)	0.0135 (5)	0.0139 (6)	−0.0006 (4)	−0.0027 (4)	−0.0007 (4)
C10	0.0138 (5)	0.0144 (6)	0.0204 (7)	−0.0012 (4)	−0.0025 (5)	0.0012 (5)
C11	0.0146 (5)	0.0161 (6)	0.0193 (7)	0.0004 (4)	0.0012 (5)	0.0012 (5)
C12	0.0159 (5)	0.0142 (5)	0.0135 (6)	0.0005 (4)	0.0021 (5)	0.0000 (5)
C13	0.0132 (5)	0.0115 (5)	0.0111 (5)	−0.0001 (4)	−0.0004 (4)	0.0002 (4)
C14	0.0128 (5)	0.0128 (5)	0.0112 (5)	0.0003 (4)	−0.0006 (4)	0.0002 (4)
C15	0.0135 (5)	0.0121 (5)	0.0092 (5)	0.0001 (4)	−0.0007 (4)	−0.0005 (4)

O1—C14	1.2193 (18)	C7—C15	1.4321 (19)
N1—C15	1.3070 (17)	C7—C8	1.4768 (17)
N1—C1	1.3793 (18)	C8—C9	1.3865 (18)
N2—C7	1.3142 (17)	C8—C13	1.4106 (19)
N2—C6	1.3800 (17)	C9—C10	1.402 (2)
C1—C2	1.4197 (17)	C9—H9A	0.97 (3)
C1—C6	1.4292 (18)	C10—C11	1.401 (2)
C2—C3	1.377 (2)	C10—H10A	0.98 (3)
C2—H2A	0.99 (3)	C11—C12	1.399 (2)
C3—C4	1.413 (2)	C11—H11A	0.98 (3)
C3—H3A	0.96 (2)	C12—C13	1.3935 (18)
C4—C5	1.381 (2)	C12—H12A	0.97 (3)
C4—H4A	0.98 (3)	C13—C14	1.4876 (18)
C5—C6	1.4140 (19)	C14—C15	1.509 (2)
C5—H5A	1.00 (3)
C15—N1—C1	113.99 (12)	C9—C8—C7	130.26 (13)
C7—N2—C6	114.00 (12)	C13—C8—C7	108.50 (11)
N1—C1—C2	118.59 (13)	C8—C9—C10	117.57 (14)
N1—C1—C6	121.85 (12)	C8—C9—H9A	122.5 (13)
C2—C1—C6	119.55 (13)	C10—C9—H9A	119.9 (13)
C3—C2—C1	119.96 (14)	C11—C10—C9	121.35 (13)
C3—C2—H2A	118.1 (14)	C11—C10—H10A	119.6 (15)
C1—C2—H2A	121.9 (14)	C9—C10—H10A	119.0 (15)
C2—C3—C4	120.54 (13)	C12—C11—C10	121.02 (13)
C2—C3—H3A	121.2 (16)	C12—C11—H11A	122.4 (16)
C4—C3—H3A	118.3 (16)	C10—C11—H11A	116.5 (16)
C5—C4—C3	120.66 (13)	C13—C12—C11	117.61 (14)
C5—C4—H4A	124.1 (17)	C13—C12—H12A	126 (2)
C3—C4—H4A	115.2 (17)	C11—C12—H12A	117 (2)
C4—C5—C6	120.21 (14)	C12—C13—C8	121.20 (13)
C4—C5—H5A	126.7 (15)	C12—C13—C14	128.92 (14)
C6—C5—H5A	113.1 (15)	C8—C13—C14	109.87 (11)
N2—C6—C5	118.62 (13)	O1—C14—C13	128.22 (13)
N2—C6—C1	122.31 (12)	O1—C14—C15	126.88 (12)
C5—C6—C1	119.07 (12)	C13—C14—C15	104.86 (11)
N2—C7—C15	123.41 (13)	N1—C15—C7	124.43 (13)
N2—C7—C8	128.27 (12)	N1—C15—C14	127.18 (12)
C15—C7—C8	108.32 (12)	C7—C15—C14	108.39 (12)
C9—C8—C13	121.23 (12)
C15—N1—C1—C2	179.01 (12)	C8—C9—C10—C11	−0.1 (2)
C15—N1—C1—C6	0.06 (18)	C9—C10—C11—C12	0.9 (2)
N1—C1—C2—C3	−178.21 (13)	C10—C11—C12—C13	−0.7 (2)
C6—C1—C2—C3	0.8 (2)	C11—C12—C13—C8	−0.3 (2)
C1—C2—C3—C4	−0.8 (2)	C11—C12—C13—C14	178.39 (13)
C2—C3—C4—C5	0.3 (2)	C9—C8—C13—C12	1.12 (19)
C3—C4—C5—C6	0.2 (2)	C7—C8—C13—C12	−179.14 (12)
C7—N2—C6—C5	−178.35 (12)	C9—C8—C13—C14	−177.81 (12)
C7—N2—C6—C1	1.21 (18)	C7—C8—C13—C14	1.93 (14)
C4—C5—C6—N2	179.42 (13)	C12—C13—C14—O1	−3.7 (2)
C4—C5—C6—C1	−0.1 (2)	C8—C13—C14—O1	175.12 (13)
N1—C1—C6—N2	−0.9 (2)	C12—C13—C14—C15	178.69 (14)
C2—C1—C6—N2	−179.87 (13)	C8—C13—C14—C15	−2.50 (14)
N1—C1—C6—C5	178.63 (12)	C1—N1—C15—C7	0.42 (19)
C2—C1—C6—C5	−0.32 (19)	C1—N1—C15—C14	−178.69 (12)
C6—N2—C7—C15	−0.74 (18)	N2—C7—C15—N1	−0.1 (2)
C6—N2—C7—C8	179.53 (12)	C8—C7—C15—N1	179.70 (12)
N2—C7—C8—C9	−1.1 (2)	N2—C7—C15—C14	179.18 (12)
C15—C7—C8—C9	179.17 (14)	C8—C7—C15—C14	−1.05 (14)
N2—C7—C8—C13	179.22 (13)	O1—C14—C15—N1	3.7 (2)
C15—C7—C8—C13	−0.53 (14)	C13—C14—C15—N1	−178.64 (12)
C13—C8—C9—C10	−0.89 (19)	O1—C14—C15—C7	−175.53 (13)
C7—C8—C9—C10	179.44 (13)	C13—C14—C15—C7	2.13 (14)

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)

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)

Symmetry codes: (i) ; (ii) .