Pyrazino[2,3-b]indolizine-10-carbonitrile.

In the crystal structure of the title compound, C(11)H(6)N(4), neighbouring mol-ecules are linked into inversion dimers through pairs of weak C-H⋯N hydrogen bonds, forming an R(2) (2)(10) ring motif. The dimers forming this motif are further linked by π-π inter-actions. With respective average deviations from planarity of 0.004 (2) and 0.004 (1) Å, the pyrazino[2,3-β]indolizine and cyano fragment are oriented at 0.8 (1)° to each other. The mean planes of the pyrazino[2,3-b]indolizine skeleton either lie parallel or are inclined at an angle of 28.7 (2)° in the crystal.

Related literature

For applications of this class of compounds, see: Akiyama et al. (1978 ▶); Foks et al. (2005 ▶); Kaliszan et al. (1985 ▶); Kushner et al. (1952 ▶); Mussinan et al. (1973 ▶); Petrusewicz et al. (1993 ▶, 1995 ▶); Seitz et al. (2002 ▶). For the synthesis, see: Pilarski & Foks (1981 ▶ and 1982 ▶). For the analysis of inter­molecular inter­actions, see: Spek (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen bonds, see: Steiner (1999 ▶).

Experimental

Crystal data

C11H6N4

M = 194.20

Monoclinic,

a = 3.8515 (5) Å

b = 14.147 (2) Å

c = 16.606 (3) Å

β = 91.260 (14)°

V = 904.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.08 × 0.06 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.992, T max = 0.999

6832 measured reflections

1606 independent reflections

1186 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.02

1606 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008939/ww2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008939/ww2144Isup2.hkl

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

C11H6N4	F(000) = 400
Mr = 194.20	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6832 reflections
a = 3.8515 (5) Å	θ = 3.0–25.0°
b = 14.147 (2) Å	µ = 0.09 mm−1
c = 16.606 (3) Å	T = 295 K
β = 91.260 (14)°	Needle, orange-green
V = 904.6 (2) Å3	0.30 × 0.08 × 0.06 mm
Z = 4

Oxford Diffraction Ruby CCD diffractometer	1606 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1186 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −16→15
Tmin = 0.992, Tmax = 0.999	l = −18→19
6832 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0745P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1606 reflections	Δρmax = 0.18 e Å−3
137 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (5)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > σ(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
N1	0.1906 (3)	0.18749 (8)	0.01142 (7)	0.0395 (3)
C2	0.3590 (4)	0.15549 (12)	−0.05644 (9)	0.0463 (4)
H2	0.4296	0.0928	−0.0597	0.056*
C3	0.4196 (4)	0.21534 (13)	−0.11734 (10)	0.0541 (5)
H3	0.5303	0.1943	−0.1632	0.065*
C4	0.3135 (4)	0.31070 (13)	−0.11094 (11)	0.0554 (5)
H4	0.3574	0.3523	−0.1529	0.066*
C5	0.1475 (4)	0.34299 (12)	−0.04437 (10)	0.0506 (4)
H5	0.0804	0.4060	−0.0415	0.061*
C6	0.0772 (4)	0.28097 (10)	0.02016 (9)	0.0412 (4)
C7	−0.0876 (4)	0.29055 (10)	0.09485 (9)	0.0431 (4)
C8	−0.0708 (4)	0.20124 (11)	0.13408 (9)	0.0410 (4)
N9	−0.1882 (3)	0.17236 (10)	0.20656 (8)	0.0500 (4)
C10	−0.1199 (4)	0.08189 (13)	0.22182 (10)	0.0538 (5)
H10	−0.1906	0.0569	0.2706	0.065*
C11	0.0522 (4)	0.02209 (12)	0.16866 (10)	0.0528 (4)
H11	0.0890	−0.0403	0.1844	0.063*
N12	0.1684 (3)	0.04892 (9)	0.09592 (8)	0.0482 (4)
C13	0.1002 (3)	0.13879 (10)	0.08115 (9)	0.0387 (4)
C14	−0.2351 (4)	0.37523 (12)	0.12502 (10)	0.0528 (5)
N15	−0.3567 (4)	0.44383 (12)	0.14836 (11)	0.0782 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0429 (6)	0.0342 (7)	0.0413 (7)	0.0010 (5)	−0.0001 (5)	−0.0047 (5)
C2	0.0487 (8)	0.0447 (9)	0.0455 (9)	0.0043 (7)	0.0020 (7)	−0.0093 (7)
C3	0.0561 (10)	0.0600 (12)	0.0466 (10)	0.0024 (8)	0.0074 (8)	−0.0039 (8)
C4	0.0558 (9)	0.0571 (11)	0.0533 (11)	−0.0042 (8)	0.0013 (8)	0.0129 (8)
C5	0.0533 (9)	0.0398 (9)	0.0586 (11)	−0.0007 (7)	−0.0023 (8)	0.0044 (8)
C6	0.0401 (7)	0.0331 (8)	0.0501 (10)	−0.0016 (6)	−0.0033 (7)	−0.0045 (7)
C7	0.0463 (8)	0.0351 (9)	0.0479 (9)	0.0010 (6)	0.0007 (7)	−0.0075 (7)
C8	0.0407 (8)	0.0406 (9)	0.0415 (9)	−0.0042 (6)	−0.0013 (6)	−0.0059 (7)
N9	0.0535 (7)	0.0499 (10)	0.0467 (9)	−0.0028 (6)	0.0035 (6)	−0.0017 (6)
C10	0.0568 (9)	0.0560 (12)	0.0485 (10)	−0.0065 (8)	0.0020 (8)	0.0058 (8)
C11	0.0607 (9)	0.0430 (10)	0.0543 (10)	−0.0034 (8)	−0.0049 (8)	0.0086 (8)
N12	0.0545 (7)	0.0373 (8)	0.0525 (8)	0.0030 (6)	−0.0043 (6)	−0.0006 (6)
C13	0.0407 (7)	0.0339 (9)	0.0413 (9)	−0.0012 (6)	−0.0026 (6)	−0.0032 (6)
C14	0.0552 (9)	0.0436 (11)	0.0597 (11)	0.0000 (8)	0.0016 (8)	−0.0123 (8)
N15	0.0841 (11)	0.0517 (11)	0.0992 (13)	0.0092 (8)	0.0080 (10)	−0.0274 (9)

N1—C2	1.3883 (19)	C7—C14	1.422 (2)
N1—C13	1.3980 (18)	C7—C8	1.422 (2)
N1—C6	1.4014 (18)	C8—N9	1.3580 (19)
C2—C3	1.343 (2)	C8—C13	1.419 (2)
C2—H2	0.9300	N9—C10	1.330 (2)
C3—C4	1.414 (3)	C10—C11	1.400 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.368 (2)	C11—N12	1.352 (2)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.416 (2)	N12—C13	1.3201 (19)
C5—H5	0.9300	C14—N15	1.149 (2)
C6—C7	1.412 (2)
C2—N1—C13	129.87 (13)	C6—C7—C14	125.53 (14)
C2—N1—C6	122.96 (13)	C6—C7—C8	107.47 (12)
C13—N1—C6	107.18 (11)	C14—C7—C8	126.98 (15)
C3—C2—N1	119.85 (15)	N9—C8—C13	122.01 (14)
C3—C2—H2	120.1	N9—C8—C7	131.34 (14)
N1—C2—H2	120.1	C13—C8—C7	106.65 (13)
C2—C3—C4	119.29 (15)	C10—N9—C8	112.96 (13)
C2—C3—H3	120.4	N9—C10—C11	123.77 (15)
C4—C3—H3	120.4	N9—C10—H10	118.1
C5—C4—C3	121.36 (16)	C11—C10—H10	118.1
C5—C4—H4	119.3	N12—C11—C10	124.36 (15)
C3—C4—H4	119.3	N12—C11—H11	117.8
C4—C5—C6	120.35 (16)	C10—C11—H11	117.8
C4—C5—H5	119.8	C13—N12—C11	111.60 (13)
C6—C5—H5	119.8	N12—C13—N1	125.19 (13)
N1—C6—C7	109.19 (12)	N12—C13—C8	125.30 (14)
N1—C6—C5	116.18 (13)	N1—C13—C8	109.50 (13)
C7—C6—C5	134.63 (14)	N15—C14—C7	179.0 (2)
C13—N1—C2—C3	179.88 (14)	C6—C7—C8—C13	−0.94 (16)
C6—N1—C2—C3	0.1 (2)	C14—C7—C8—C13	−179.67 (14)
N1—C2—C3—C4	0.6 (2)	C13—C8—N9—C10	1.07 (19)
C2—C3—C4—C5	−0.6 (2)	C7—C8—N9—C10	−179.86 (16)
C3—C4—C5—C6	−0.1 (2)	C8—N9—C10—C11	−0.5 (2)
C2—N1—C6—C7	179.16 (12)	N9—C10—C11—N12	−0.1 (3)
C13—N1—C6—C7	−0.67 (14)	C10—C11—N12—C13	0.2 (2)
C2—N1—C6—C5	−0.79 (19)	C11—N12—C13—N1	179.34 (12)
C13—N1—C6—C5	179.38 (12)	C11—N12—C13—C8	0.4 (2)
C4—C5—C6—N1	0.8 (2)	C2—N1—C13—N12	1.2 (2)
C4—C5—C6—C7	−179.16 (15)	C6—N1—C13—N12	−178.99 (13)
N1—C6—C7—C14	179.76 (14)	C2—N1—C13—C8	−179.75 (12)
C5—C6—C7—C14	−0.3 (3)	C6—N1—C13—C8	0.07 (14)
N1—C6—C7—C8	1.01 (15)	N9—C8—C13—N12	−1.1 (2)
C5—C6—C7—C8	−179.06 (15)	C7—C8—C13—N12	179.60 (14)
C6—C7—C8—N9	179.88 (14)	N9—C8—C13—N1	179.82 (11)
C14—C7—C8—N9	1.2 (3)	C7—C8—C13—N1	0.55 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N12i	0.93	2.61	3.487 (2)	157

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
A	Bii	3.608 (1)	0.6	3.358 (1)	1.320 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N12i	0.93	2.61	3.487 (2)	157

Symmetry code: (i) .

Table 2

π–π interactions (Å, °)

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
A	Bii	3.608 (1)	0.6	3.358 (1)	1.320 (1)

Symmetry codes: (ii) . Notes: CgA and CgB are the centroids of the N1/C6–C8/C13 and N1/C2–C6 rings, respectively. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.