5H-Imidazo[4,5-f][1,10]phenanthroline.

The title mol-ecule, C(13)H(8)N(4), is is essentially planar [r.m.s. deviation for all non-H atoms = 0.025 (3) Å]. In the crystal, mol-ecules are connected through one weak bifurcated N-H⋯(N,N) hydrogen bond and three π-π stacking inter-actions between pyridine and imidazole rings [centroid-centroid distance = 3.631 (8) Å] and between pyridine and benzene rings [centroid-centroid distances = 3.675 (5) and 3.666 (2) Å].

Related literature

For our previous work based on 1,10-phenanthroline as anauxiliary ligand, see: Song et al. (2009 ▶); Hao et al. (2008 ▶). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999 ▶).

Experimental

Crystal data

C13H8N4

M = 220.23

Orthorhombic,

a = 14.569 (2) Å

b = 7.8623 (12) Å

c = 17.042 (3) Å

V = 1952.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.26 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.980, T max = 0.985

5772 measured reflections

1756 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.00

1756 reflections

186 parameters

All H-atom parameters refined

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016595/bx2404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016595/bx2404Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016595/bx2404Isup3.cml

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

C13H8N4	F(000) = 912
Mr = 220.23	Dx = 1.499 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 799 reflections
a = 14.569 (2) Å	θ = 2.2–27.5°
b = 7.8623 (12) Å	µ = 0.10 mm−1
c = 17.042 (3) Å	T = 296 K
V = 1952.1 (5) Å3	Block, yellow
Z = 8	0.26 × 0.18 × 0.16 mm

Bruker APEXII CCD diffractometer	1756 independent reflections
Radiation source: fine-focus sealed tube	1025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→10
Tmin = 0.980, Tmax = 0.985	k = −9→9
5772 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	All H-atom parameters refined
S = 1.00	w = 1/[σ2(Fo2) + (0.0606P)2] where P = (Fo2 + 2Fc2)/3
1756 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 > 2sigma(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
N2	0.08583 (13)	0.0741 (3)	0.18218 (11)	0.0428 (6)
C13	0.17857 (16)	0.0868 (3)	0.18200 (12)	0.0349 (6)
C4	0.22247 (15)	0.1620 (3)	0.25102 (12)	0.0347 (6)
N1	0.16716 (13)	0.2161 (3)	0.30974 (10)	0.0423 (6)
C5	0.31923 (15)	0.1740 (3)	0.25518 (12)	0.0355 (6)
N3	0.46339 (14)	0.1051 (3)	0.17574 (13)	0.0471 (6)
N4	0.39502 (14)	−0.0018 (3)	0.06803 (11)	0.0449 (6)
C11	0.09449 (19)	−0.0623 (4)	0.05615 (15)	0.0487 (7)
C12	0.04717 (19)	−0.0004 (3)	0.12071 (16)	0.0494 (7)
C3	0.20665 (19)	0.2840 (3)	0.37251 (14)	0.0460 (7)
C2	0.30087 (18)	0.3045 (3)	0.38092 (14)	0.0439 (7)
C1	0.35746 (19)	0.2504 (3)	0.32252 (13)	0.0416 (6)
C6	0.37040 (15)	0.1101 (3)	0.18996 (12)	0.0365 (6)
C7	0.4727 (2)	0.0392 (3)	0.10225 (15)	0.0514 (7)
C8	0.32970 (16)	0.0437 (3)	0.12418 (12)	0.0373 (6)
C9	0.23250 (15)	0.0280 (3)	0.11878 (12)	0.0356 (6)
C10	0.18762 (19)	−0.0478 (3)	0.05489 (14)	0.0445 (7)
H7	0.5396 (16)	0.027 (3)	0.0759 (12)	0.042 (6)*
H6	0.2264 (16)	−0.088 (3)	0.0121 (15)	0.056 (8)*
H4	−0.0192 (17)	−0.012 (3)	0.1232 (13)	0.045 (7)*
H1	0.4230 (16)	0.270 (3)	0.3229 (13)	0.051 (8)*
H5	0.0590 (16)	−0.125 (3)	0.0140 (15)	0.063 (8)*
H3	0.1640 (15)	0.322 (3)	0.4153 (13)	0.046 (7)*
H2	0.3235 (16)	0.353 (3)	0.4266 (14)	0.053 (7)*
H8	0.5057 (19)	0.136 (4)	0.2135 (18)	0.074 (9)*

	U11	U22	U33	U12	U13	U23
N2	0.0304 (12)	0.0574 (14)	0.0407 (12)	−0.0012 (10)	−0.0020 (9)	0.0005 (10)
C13	0.0326 (13)	0.0403 (15)	0.0318 (12)	−0.0009 (11)	−0.0029 (11)	0.0052 (10)
C4	0.0343 (13)	0.0379 (14)	0.0319 (11)	0.0024 (12)	0.0035 (11)	0.0054 (10)
N1	0.0396 (12)	0.0519 (14)	0.0355 (11)	0.0021 (10)	0.0037 (10)	0.0001 (9)
C5	0.0350 (14)	0.0389 (14)	0.0326 (12)	−0.0016 (11)	−0.0027 (11)	0.0075 (10)
N3	0.0308 (12)	0.0644 (15)	0.0462 (13)	0.0046 (11)	−0.0024 (11)	0.0001 (11)
N4	0.0334 (12)	0.0646 (15)	0.0368 (11)	0.0021 (11)	0.0034 (10)	0.0000 (10)
C11	0.0435 (17)	0.0584 (18)	0.0441 (15)	−0.0023 (14)	−0.0125 (13)	−0.0028 (13)
C12	0.0326 (15)	0.0651 (19)	0.0505 (15)	−0.0029 (14)	−0.0084 (13)	−0.0022 (13)
C3	0.0488 (17)	0.0546 (18)	0.0346 (14)	0.0041 (13)	0.0018 (12)	−0.0029 (11)
C2	0.0511 (17)	0.0462 (16)	0.0344 (13)	−0.0027 (13)	−0.0045 (12)	−0.0036 (11)
C1	0.0403 (15)	0.0443 (15)	0.0403 (14)	−0.0014 (13)	−0.0053 (13)	0.0029 (11)
C6	0.0305 (13)	0.0445 (15)	0.0344 (12)	0.0013 (11)	0.0015 (10)	0.0047 (11)
C7	0.0401 (17)	0.0647 (19)	0.0495 (15)	0.0122 (15)	0.0068 (14)	0.0010 (13)
C8	0.0335 (14)	0.0447 (16)	0.0338 (12)	0.0021 (12)	0.0013 (11)	0.0039 (10)
C9	0.0375 (14)	0.0372 (14)	0.0321 (12)	0.0020 (11)	−0.0006 (10)	0.0048 (10)
C10	0.0471 (17)	0.0518 (17)	0.0346 (13)	0.0026 (14)	−0.0025 (12)	0.0009 (11)

N2—C12	1.326 (3)	C11—C10	1.362 (4)
N2—C13	1.355 (3)	C11—C12	1.387 (4)
C13—C9	1.411 (3)	C11—H5	1.01 (3)
C13—C4	1.464 (3)	C12—H4	0.97 (2)
C4—N1	1.353 (3)	C3—C2	1.390 (4)
C4—C5	1.415 (3)	C3—H3	1.00 (2)
N1—C3	1.327 (3)	C2—C1	1.360 (3)
C5—C1	1.410 (3)	C2—H2	0.93 (2)
C5—C6	1.429 (3)	C1—H1	0.97 (2)
N3—C7	1.362 (3)	C6—C8	1.372 (3)
N3—C6	1.377 (3)	C7—H7	1.08 (2)
N3—H8	0.92 (3)	C8—C9	1.424 (3)
N4—C7	1.314 (3)	C9—C10	1.403 (3)
N4—C8	1.396 (3)	C10—H6	0.98 (3)
C12—N2—C13	117.0 (2)	C2—C3—H3	120.2 (13)
N2—C13—C9	122.2 (2)	C1—C2—C3	119.2 (2)
N2—C13—C4	117.63 (19)	C1—C2—H2	121.8 (15)
C9—C13—C4	120.2 (2)	C3—C2—H2	119.0 (15)
N1—C4—C5	122.4 (2)	C2—C1—C5	119.3 (2)
N1—C4—C13	117.4 (2)	C2—C1—H1	123.0 (14)
C5—C4—C13	120.16 (19)	C5—C1—H1	117.5 (14)
C3—N1—C4	117.7 (2)	C8—C6—N3	105.7 (2)
C1—C5—C4	117.6 (2)	C8—C6—C5	122.9 (2)
C1—C5—C6	125.2 (2)	N3—C6—C5	131.3 (2)
C4—C5—C6	117.2 (2)	N4—C7—N3	114.5 (2)
C7—N3—C6	105.7 (2)	N4—C7—H7	124.9 (11)
C7—N3—H8	132.4 (17)	N3—C7—H7	120.5 (11)
C6—N3—H8	121.7 (17)	C6—C8—N4	111.3 (2)
C7—N4—C8	102.7 (2)	C6—C8—C9	121.0 (2)
C10—C11—C12	118.6 (2)	N4—C8—C9	127.7 (2)
C10—C11—H5	122.6 (13)	C10—C9—C13	118.2 (2)
C12—C11—H5	118.7 (13)	C10—C9—C8	123.4 (2)
N2—C12—C11	124.8 (2)	C13—C9—C8	118.4 (2)
N2—C12—H4	115.4 (14)	C11—C10—C9	119.2 (2)
C11—C12—H4	119.7 (14)	C11—C10—H6	124.2 (14)
N1—C3—C2	123.9 (2)	C9—C10—H6	116.6 (14)
N1—C3—H3	115.9 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H8···N1i	0.92 (3)	2.47 (3)	3.104 (3)	126 (2)
N3—H8···N2i	0.92 (3)	2.18 (3)	3.017 (3)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H8⋯N1i	0.92 (3)	2.47 (3)	3.104 (3)	126 (2)
N3—H8⋯N2i	0.92 (3)	2.18 (3)	3.017 (3)	150 (2)

Symmetry code: (i) .