3-Iodo-1H-pyrazolo-[3,4-b]pyridine.

The title compound, C6H4IN3, is essentially planar, with a dihedral angle of 0.82 (3)° between the planes of the pyridine and pyrazole rings. In the crystal, pairs of mol-ecules are connected into inversion dimers through N-H⋯N hydrogen bonds. C-I⋯N halogen bonds link the dimers into zigzag chains parallel to the b-axis direction. The packing also features π-π stacking inter-actions along (110) with inter-planar distances of 3.292 (1) and 3.343 (1) Å, and centroid-centroid distances of 3.308 (1) and 3.430 (1) Å.

Related literature

For the production of anti­tumor agents, see: Huang et al. (2007 ▶); Ye et al. (2009 ▶). For a related structure, see: Huang et al. (2013 ▶).

Experimental

Crystal data

C6H4IN3

M = 245.02

Monoclinic,

a = 10.7999 (13) Å

b = 7.7939 (9) Å

c = 17.406 (2) Å

β = 101.748 (2)°

V = 1434.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 4.38 mm−1

T = 150 K

0.35 × 0.32 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1996 ▶) T min = 0.309, T max = 0.407

5315 measured reflections

1470 independent reflections

1423 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.040

S = 1.13

1470 reflections

91 parameters

26 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT (Bruker, 2001 ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) ic14830, I. DOI: 10.1107/S1600536814010009/zl2581sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010009/zl2581Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010009/zl2581Isup3.cml

CCDC reference: 1000735

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H4IN3	F(000) = 912
Mr = 245.02	Dx = 2.269 Mg m−3Dm = 2.269 Mg m−3Dm measured by not measured
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7999 (13) Å	Cell parameters from 4550 reflections
b = 7.7939 (9) Å	θ = 2.4–27.5°
c = 17.406 (2) Å	µ = 4.38 mm−1
β = 101.748 (2)°	T = 150 K
V = 1434.5 (3) Å3	Block, colorless
Z = 8	0.35 × 0.32 × 0.25 mm

Bruker SMART APEX CCD area-detector diffractometer	1470 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1996)	h = −14→13
Tmin = 0.309, Tmax = 0.407	k = −10→9
5315 measured reflections	l = −22→22

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.040	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0156P)2 + 1.9173P] where P = (Fo2 + 2Fc2)/3
1470 reflections	(Δ/σ)max = 0.003
91 parameters	Δρmax = 0.40 e Å−3
26 restraints	Δρmin = −0.46 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
I1	0.23044 (2)	1.04283 (2)	0.29263 (2)	0.02252 (7)
N1	0.46725 (18)	0.6969 (3)	0.56007 (11)	0.0202 (4)
N2	0.44327 (18)	0.6579 (3)	0.42063 (11)	0.0196 (4)
H2A	0.4869	0.5622	0.4219	0.023*
N3	0.38503 (19)	0.7396 (3)	0.35341 (11)	0.0201 (4)
C1	0.4368 (2)	0.8083 (3)	0.61183 (13)	0.0226 (5)
H1	0.4641	0.7822	0.6660	0.027*
C2	0.3682 (2)	0.9594 (3)	0.59272 (15)	0.0249 (5)
H2	0.3517	1.0325	0.6332	0.030*
C3	0.3242 (2)	1.0027 (3)	0.51533 (15)	0.0223 (5)
H3	0.2758	1.1038	0.5010	0.027*
C4	0.3539 (2)	0.8915 (3)	0.45868 (13)	0.0177 (4)
C5	0.4249 (2)	0.7441 (3)	0.48502 (13)	0.0178 (4)
C6	0.3326 (2)	0.8785 (3)	0.37596 (13)	0.0189 (4)

	U11	U22	U33	U12	U13	U23
I1	0.02567 (11)	0.01896 (10)	0.02189 (10)	0.00157 (6)	0.00242 (7)	0.00504 (6)
N1	0.0215 (10)	0.0196 (10)	0.0186 (9)	−0.0028 (8)	0.0020 (8)	0.0012 (8)
N2	0.0222 (10)	0.0173 (10)	0.0184 (9)	0.0042 (8)	0.0020 (8)	0.0004 (7)
N3	0.0229 (10)	0.0192 (10)	0.0174 (9)	−0.0007 (8)	0.0022 (8)	0.0019 (8)
C1	0.0264 (13)	0.0240 (12)	0.0174 (10)	−0.0075 (10)	0.0043 (9)	−0.0015 (9)
C2	0.0281 (14)	0.0234 (13)	0.0252 (12)	−0.0062 (10)	0.0105 (10)	−0.0064 (10)
C3	0.0241 (13)	0.0159 (11)	0.0287 (12)	−0.0020 (10)	0.0097 (10)	−0.0022 (9)
C4	0.0181 (11)	0.0138 (11)	0.0218 (11)	−0.0036 (9)	0.0051 (9)	0.0011 (9)
C5	0.0171 (11)	0.0160 (11)	0.0200 (11)	−0.0037 (9)	0.0031 (8)	−0.0009 (8)
C6	0.0187 (11)	0.0168 (11)	0.0205 (11)	−0.0006 (9)	0.0023 (9)	0.0026 (9)

I1—C6	2.076 (2)	C1—H1	0.9500
N1—C1	1.339 (3)	C2—C3	1.376 (4)
N1—C5	1.345 (3)	C2—H2	0.9500
N2—C5	1.356 (3)	C3—C4	1.398 (3)
N2—N3	1.368 (3)	C3—H3	0.9500
N2—H2A	0.8800	C4—C5	1.405 (3)
N3—C6	1.318 (3)	C4—C6	1.415 (3)
C1—C2	1.396 (4)
C1—N1—C5	113.2 (2)	C2—C3—H3	121.5
C5—N2—N3	110.93 (18)	C4—C3—H3	121.5
C5—N2—H2A	124.5	C3—C4—C5	117.7 (2)
N3—N2—H2A	124.5	C3—C4—C6	138.5 (2)
C6—N3—N2	106.15 (18)	C5—C4—C6	103.79 (19)
N1—C1—C2	125.3 (2)	N1—C5—N2	126.1 (2)
N1—C1—H1	117.4	N1—C5—C4	126.6 (2)
C2—C1—H1	117.4	N2—C5—C4	107.31 (19)
C3—C2—C1	120.1 (2)	N3—C6—C4	111.8 (2)
C3—C2—H2	120.0	N3—C6—I1	119.88 (16)
C1—C2—H2	120.0	C4—C6—I1	128.30 (17)
C2—C3—C4	117.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.88	2.09	2.926 (3)	159
C6—I1···N3ii	2.08 (1)	3.01 (1)	5.056 (3)	167 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.88	2.09	2.926 (3)	159
C6—I1⋯N3ii	2.076 (2)	3.013 (2)	5.056 (3)	166.72 (7)

Symmetry codes: (i) ; (ii) .