6,6'-(Pyridine-2,6-di-yl)bis-(pyrrolo-[3,4-b]pyridine-5,7-dione).

The title compound, C(19)H(9)N(5)O(4), has crystallographically imposed twofold rotational symmetry. The asymmetric unit contains one half-mol-ecule. The crystal structure is stabilized by π-π stacking of inversion-related pyrrolo-[3,4-b]pyridine rings, with a centroid-centroid distance between stacked pyridines of 3.6960 (8) Å. The dihedral angle between the central pyridine ring and the pyrrolo-pyridine side rings is 77.86 (2)° while the angle between the two side chains is 60.87 (2)°.

Related literature

For related structures, see: Jain et al. (2004 ▶). For related metal complexes, see: Schutte et al. (2009 ▶, 2010 ▶); Brink et al. (2011 ▶).

Experimental

Crystal data

C19H9N5O4

M = 371.31

Monoclinic,

a = 14.539 (1) Å

b = 7.391 (1) Å

c = 15.686 (1) Å

β = 108.752 (2)°

V = 1596.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.34 × 0.29 × 0.27 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.681, T max = 0.746

12803 measured reflections

1920 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.06

1920 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104414X/pk2352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104414X/pk2352Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104414X/pk2352Isup3.cml

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

C19H9N5O4	F(000) = 760
Mr = 371.31	Dx = 1.545 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.539 (1) Å	Cell parameters from 6738 reflections
b = 7.391 (1) Å	θ = 2.7–28.3°
c = 15.686 (1) Å	µ = 0.11 mm−1
β = 108.752 (2)°	T = 100 K
V = 1596.1 (3) Å3	Cuboid, colourless
Z = 4	0.34 × 0.29 × 0.27 mm

Bruker X8 APEXII 4K KappaCCD diffractometer	1920 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 28°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→15
Tmin = 0.681, Tmax = 0.746	k = −9→9
12803 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.2599P] where P = (Fo2 + 2Fc2)/3
1920 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1758 frames were collected with a frame width of 0.5° covering up to θ = 28.00° with 99.3% completeness accomplished.

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	−0.05122 (6)	0.18475 (11)	0.00789 (5)	0.0226 (2)
O2	0.22325 (6)	0.31769 (14)	0.24267 (6)	0.0327 (2)
N1	0	0.22247 (19)	0.25	0.0206 (3)
N2	0.07684 (7)	0.22769 (13)	0.13958 (6)	0.0209 (2)
N3	0.07688 (7)	0.39842 (13)	−0.07379 (6)	0.0212 (2)
C7	0.17897 (8)	0.39008 (15)	0.08242 (7)	0.0210 (2)
C4	0.02795 (8)	0.24566 (15)	0.04720 (7)	0.0186 (2)
C10	0.15034 (8)	0.48687 (16)	−0.09009 (8)	0.0231 (2)
H10	0.1419	0.5224	−0.149	0.028*
C6	0.16835 (8)	0.31349 (16)	0.16665 (8)	0.0232 (2)
C5	0.09539 (8)	0.35189 (15)	0.01192 (7)	0.0184 (2)
C8	0.25407 (8)	0.48175 (16)	0.06507 (8)	0.0249 (3)
H8	0.3115	0.5102	0.1104	0.03*
C9	0.23809 (8)	0.52873 (16)	−0.02460 (8)	0.0246 (3)
H9	0.2863	0.5884	−0.0407	0.029*
C3	0.03783 (8)	0.12612 (16)	0.19763 (7)	0.0205 (2)
C2	0.04021 (8)	−0.06106 (16)	0.19451 (7)	0.0228 (2)
H2	0.0678	−0.1208	0.1565	0.027*
C1	0	−0.1562 (2)	0.25	0.0237 (3)
H1	0	−0.282	0.25	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.0175 (4)	0.0269 (4)	0.0224 (4)	−0.0041 (3)	0.0052 (3)	−0.0019 (3)
O2	0.0241 (5)	0.0474 (6)	0.0219 (4)	−0.0071 (4)	0.0010 (4)	−0.0015 (4)
N1	0.0173 (6)	0.0254 (7)	0.0177 (6)	0	0.0037 (5)	0
N2	0.0179 (5)	0.0265 (5)	0.0180 (4)	−0.0026 (4)	0.0053 (4)	−0.0012 (4)
N3	0.0210 (5)	0.0210 (5)	0.0226 (5)	0.0000 (4)	0.0084 (4)	−0.0002 (4)
C7	0.0184 (5)	0.0217 (5)	0.0223 (5)	0.0000 (4)	0.0059 (4)	−0.0032 (4)
C4	0.0182 (5)	0.0193 (5)	0.0187 (5)	0.0010 (4)	0.0064 (4)	−0.0017 (4)
C10	0.0250 (6)	0.0208 (5)	0.0262 (5)	0.0007 (4)	0.0120 (5)	0.0008 (4)
C6	0.0189 (5)	0.0268 (6)	0.0230 (5)	−0.0019 (4)	0.0053 (4)	−0.0033 (4)
C5	0.0162 (5)	0.0176 (5)	0.0221 (5)	0.0005 (4)	0.0070 (4)	−0.0027 (4)
C8	0.0177 (5)	0.0251 (6)	0.0306 (6)	−0.0027 (4)	0.0062 (5)	−0.0037 (5)
C9	0.0214 (5)	0.0206 (5)	0.0352 (6)	−0.0021 (4)	0.0141 (5)	−0.0011 (5)
C3	0.0168 (5)	0.0271 (6)	0.0162 (5)	−0.0012 (4)	0.0033 (4)	−0.0001 (4)
C2	0.0227 (5)	0.0272 (6)	0.0168 (5)	0.0012 (4)	0.0043 (4)	−0.0023 (4)
C1	0.0273 (8)	0.0232 (8)	0.0179 (7)	0	0.0036 (6)	0

O1—C4	1.2047 (13)	C4—C5	1.4944 (15)
O2—C6	1.2033 (14)	C10—C9	1.3915 (17)
N1—C3	1.3322 (13)	C10—H10	0.93
N1—C3i	1.3322 (13)	C8—C9	1.3938 (17)
N2—C4	1.4001 (14)	C8—H8	0.93
N2—C6	1.4105 (14)	C9—H9	0.93
N2—C3	1.4306 (14)	C3—C2	1.3851 (17)
N3—C5	1.3286 (14)	C2—C1	1.3860 (14)
N3—C10	1.3450 (15)	C2—H2	0.93
C7—C5	1.3840 (15)	C1—C2i	1.3860 (14)
C7—C8	1.3843 (16)	C1—H1	0.93
C7—C6	1.4904 (16)
C3—N1—C3i	115.37 (14)	N3—C5—C4	124.55 (10)
C4—N2—C6	112.63 (9)	C7—C5—C4	108.86 (9)
C4—N2—C3	122.37 (9)	C7—C8—C9	115.73 (11)
C6—N2—C3	124.95 (9)	C7—C8—H8	122.1
C5—N3—C10	113.78 (10)	C9—C8—H8	122.1
C5—C7—C8	119.22 (10)	C10—C9—C8	120.36 (11)
C5—C7—C6	108.44 (10)	C10—C9—H9	119.8
C8—C7—C6	132.32 (10)	C8—C9—H9	119.8
O1—C4—N2	125.30 (10)	N1—C3—C2	125.15 (11)
O1—C4—C5	129.75 (10)	N1—C3—N2	116.02 (10)
N2—C4—C5	104.95 (9)	C2—C3—N2	118.82 (10)
N3—C10—C9	124.28 (11)	C3—C2—C1	117.65 (11)
N3—C10—H10	117.9	C3—C2—H2	121.2
C9—C10—H10	117.9	C1—C2—H2	121.2
O2—C6—N2	124.82 (11)	C2—C1—C2i	119.04 (16)
O2—C6—C7	130.09 (11)	C2—C1—H1	120.5
N2—C6—C7	105.09 (9)	C2i—C1—H1	120.5
N3—C5—C7	126.59 (10)