2-(1H-Pyrrolo-[2,3-b]pyridin-2-yl)pyridine.

In the title compound, C(12)H(9)N(3), the dihedral angle between the pyridine and aza-indole rings is 6.20 (2)°. In the crystal, pairs of N-H⋯N hydrogen bonds link mol-ecules into inversion dimers.

Related literature

For the production of luminescent organic/organometallic compounds, see: Liu et al. (2000 ▶). For related structures, see: Sakamoto et al. (1996 ▶); Huang et al. (2011 ▶).

Experimental

Crystal data

C12H9N3

M = 195.22

Monoclinic,

a = 10.1416 (10) Å

b = 13.7428 (14) Å

c = 6.7395 (7) Å

β = 94.331 (2)°

V = 936.63 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.55 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.938, T max = 0.996

7069 measured reflections

2154 independent reflections

1792 reflections with I > 2σa(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.145

S = 1.19

2154 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023690/rk2358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023690/rk2358Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023690/rk2358Isup3.cml

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

C12H9N3	F(000) = 408
Mr = 195.22	Dx = 1.384 Mg m−3Dm = 1.384 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1871 reflections
a = 10.1416 (10) Å	θ = 2.5–26.3°
b = 13.7428 (14) Å	µ = 0.09 mm−1
c = 6.7395 (7) Å	T = 200 K
β = 94.331 (2)°	Needle, colourless
V = 936.63 (16) Å3	0.55 × 0.15 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2154 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σa(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.938, Tmax = 0.996	k = −17→17
7069 measured reflections	l = −8→8

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.2976P] where P = (Fo2 + 2Fc2)/3
2154 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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 > 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	0.66995 (16)	0.94501 (12)	0.0034 (2)	0.0382 (4)
N2	0.50593 (15)	0.92225 (11)	0.2357 (2)	0.0324 (4)
H2	0.4394	0.9513	0.1684	0.039*
N3	0.27130 (16)	0.91454 (12)	0.4136 (2)	0.0371 (4)
C1	0.7961 (2)	0.92562 (16)	−0.0253 (3)	0.0418 (5)
H1	0.8296	0.9475	−0.1454	0.050*
C2	0.8818 (2)	0.87517 (16)	0.1101 (3)	0.0412 (5)
H2A	0.9707	0.8639	0.0808	0.049*
C3	0.8377 (2)	0.84179 (14)	0.2859 (3)	0.0391 (5)
H3	0.8948	0.8070	0.3790	0.047*
C4	0.70684 (19)	0.86035 (13)	0.3238 (3)	0.0333 (4)
C5	0.62979 (18)	0.91210 (13)	0.1741 (3)	0.0316 (4)
C6	0.62305 (19)	0.84091 (13)	0.4777 (3)	0.0351 (5)
H6	0.6466	0.8073	0.5984	0.042*
C7	0.50115 (19)	0.87982 (13)	0.4198 (3)	0.0323 (4)
C8	0.37880 (18)	0.87873 (13)	0.5192 (3)	0.0327 (4)
C9	0.3725 (2)	0.84151 (14)	0.7108 (3)	0.0411 (5)
H9	0.4501	0.8179	0.7828	0.049*
C10	0.2536 (2)	0.83931 (15)	0.7945 (3)	0.0465 (6)
H10	0.2474	0.8138	0.9244	0.056*
C11	0.1429 (2)	0.87497 (16)	0.6860 (3)	0.0460 (5)
H11	0.0586	0.8738	0.7388	0.055*
C12	0.1579 (2)	0.91213 (16)	0.5003 (3)	0.0440 (5)
H12	0.0817	0.9380	0.4283	0.053*

	U11	U22	U33	U12	U13	U23
N1	0.0389 (9)	0.0415 (9)	0.0336 (9)	0.0069 (7)	−0.0001 (7)	0.0021 (7)
N2	0.0326 (8)	0.0329 (8)	0.0306 (8)	0.0031 (6)	−0.0059 (6)	0.0030 (7)
N3	0.0347 (9)	0.0376 (9)	0.0382 (9)	−0.0009 (7)	−0.0026 (7)	0.0040 (7)
C1	0.0422 (11)	0.0459 (12)	0.0373 (11)	0.0069 (9)	0.0026 (9)	0.0005 (9)
C2	0.0352 (11)	0.0435 (12)	0.0444 (12)	0.0067 (9)	−0.0013 (9)	−0.0031 (10)
C3	0.0366 (11)	0.0361 (11)	0.0426 (12)	0.0037 (8)	−0.0104 (9)	0.0006 (9)
C4	0.0379 (10)	0.0259 (9)	0.0341 (10)	−0.0004 (8)	−0.0101 (8)	−0.0009 (8)
C5	0.0336 (10)	0.0281 (9)	0.0319 (10)	0.0027 (8)	−0.0050 (8)	−0.0030 (8)
C6	0.0390 (11)	0.0298 (10)	0.0344 (10)	−0.0013 (8)	−0.0106 (8)	0.0053 (8)
C7	0.0382 (10)	0.0253 (9)	0.0321 (10)	−0.0037 (8)	−0.0065 (8)	0.0015 (8)
C8	0.0357 (10)	0.0253 (9)	0.0358 (10)	−0.0038 (7)	−0.0054 (8)	−0.0002 (8)
C9	0.0453 (12)	0.0367 (11)	0.0401 (11)	−0.0023 (9)	−0.0050 (9)	0.0062 (9)
C10	0.0566 (14)	0.0433 (12)	0.0397 (12)	−0.0035 (10)	0.0054 (10)	0.0083 (10)
C11	0.0410 (12)	0.0458 (12)	0.0521 (13)	−0.0032 (10)	0.0094 (10)	0.0023 (10)
C12	0.0393 (11)	0.0444 (12)	0.0473 (12)	0.0000 (9)	−0.0027 (9)	0.0011 (10)

N1—C5	1.328 (2)	C4—C6	1.415 (3)
N1—C1	1.335 (3)	C4—C5	1.420 (3)
N2—C5	1.360 (2)	C6—C7	1.376 (3)
N2—C7	1.376 (2)	C6—H6	0.9500
N2—H2	0.8800	C7—C8	1.454 (3)
N3—C12	1.329 (3)	C8—C9	1.395 (3)
N3—C8	1.349 (2)	C9—C10	1.369 (3)
C1—C2	1.396 (3)	C9—H9	0.9500
C1—H1	0.9500	C10—C11	1.383 (3)
C2—C3	1.377 (3)	C10—H10	0.9500
C2—H2A	0.9500	C11—C12	1.371 (3)
C3—C4	1.393 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
C5—N1—C1	114.66 (18)	C7—C6—H6	126.4
C5—N2—C7	109.17 (15)	C4—C6—H6	126.4
C5—N2—H2	125.4	N2—C7—C6	109.17 (17)
C7—N2—H2	125.4	N2—C7—C8	120.62 (16)
C12—N3—C8	116.82 (17)	C6—C7—C8	130.19 (18)
N1—C1—C2	124.1 (2)	N3—C8—C9	122.01 (18)
N1—C1—H1	117.9	N3—C8—C7	115.95 (17)
C2—C1—H1	117.9	C9—C8—C7	122.04 (18)
C3—C2—C1	120.04 (19)	C10—C9—C8	119.5 (2)
C3—C2—H2A	120.0	C10—C9—H9	120.2
C1—C2—H2A	120.0	C8—C9—H9	120.2
C2—C3—C4	118.22 (19)	C9—C10—C11	118.7 (2)
C2—C3—H3	120.9	C9—C10—H10	120.7
C4—C3—H3	120.9	C11—C10—H10	120.7
C3—C4—C6	137.09 (19)	C12—C11—C10	118.2 (2)
C3—C4—C5	116.24 (18)	C12—C11—H11	120.9
C6—C4—C5	106.67 (17)	C10—C11—H11	120.9
N1—C5—N2	125.47 (17)	N3—C12—C11	124.7 (2)
N1—C5—C4	126.71 (18)	N3—C12—H12	117.6
N2—C5—C4	107.81 (17)	C11—C12—H12	117.6
C7—C6—C4	107.17 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.88	2.10	2.944 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.88	2.10	2.944 (2)	162

Symmetry code: (i) .