4-Chloro-1H-pyrrolo-[2,3-d]pyrimidine.

The title compound, C(6)H(4)ClN(3), is essentially planar with the pyrrole and pyrimidine rings inclined to one another by 0.79 (15)°. In the crystal, mol-ecules are connected via pairs of N-H⋯N hydrogen bonds, forming inversion dimers. These dimers are linked via C-H⋯N inter-actions, forming a two-dimensional network parallel to (10-1).

Related literature

The title compound is an important organic inter­mediate in the synthesis of a drug which shows promising activity against HCV replication, see: Chang et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H4ClN3

M = 153.57

Monoclinic,

a = 10.8810 (19) Å

b = 5.2783 (9) Å

c = 12.751 (2) Å

β = 114.333 (3)°

V = 667.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.18 × 0.16 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.918, T max = 0.953

3597 measured reflections

1273 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.00

1273 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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/S1600536812034095/su2492sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034095/su2492Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034095/su2492Isup3.cml

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

C6H4ClN3	F(000) = 312
Mr = 153.57	Dx = 1.529 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4634 reflections
a = 10.8810 (19) Å	θ = 6.4–60.4°
b = 5.2783 (9) Å	µ = 0.49 mm−1
c = 12.751 (2) Å	T = 296 K
β = 114.333 (3)°	Block, colourless
V = 667.3 (2) Å3	0.18 × 0.16 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 26.0°, θmin = 3.2°
ω/2θ scans	h = −13→11
Absorption correction: ψ scan (North et al., 1968)	k = −6→6
Tmin = 0.918, Tmax = 0.953	l = −14→15
3597 measured reflections	3 standard reflections every 200 reflections
1273 independent reflections	intensity decay: 1%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0781P)2 + 0.6149P] where P = (Fo2 + 2Fc2)/3
1273 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.43 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
Cl1	0.62621 (8)	0.17642 (16)	0.50664 (6)	0.0659 (3)
C1	0.7287 (2)	0.3943 (4)	0.4803 (2)	0.0401 (5)
C2	0.8091 (2)	0.5538 (5)	0.56688 (18)	0.0385 (5)
C3	0.8403 (3)	0.6051 (6)	0.6845 (2)	0.0533 (7)
H3	0.8069	0.5213	0.7315	0.064*
C4	0.9284 (3)	0.8009 (6)	0.7143 (2)	0.0581 (7)
H4	0.9656	0.8744	0.7870	0.070*
C5	0.8835 (2)	0.7273 (4)	0.53211 (19)	0.0365 (5)
C6	0.8026 (3)	0.5695 (5)	0.3549 (2)	0.0448 (6)
H6	0.8000	0.5698	0.2810	0.054*
N1	0.9559 (2)	0.8772 (4)	0.62302 (18)	0.0470 (5)
N2	0.8820 (2)	0.7376 (4)	0.42666 (16)	0.0411 (5)
H2	0.9289	0.8447	0.4077	0.049*
N3	0.7247 (2)	0.3972 (4)	0.37545 (17)	0.0461 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0695 (5)	0.0685 (5)	0.0662 (5)	−0.0334 (4)	0.0343 (4)	−0.0032 (3)
C1	0.0408 (11)	0.0391 (11)	0.0427 (12)	−0.0039 (9)	0.0195 (9)	0.0030 (9)
C2	0.0379 (10)	0.0418 (12)	0.0393 (11)	−0.0043 (9)	0.0193 (9)	0.0025 (9)
C3	0.0585 (15)	0.0679 (17)	0.0406 (12)	−0.0180 (13)	0.0276 (11)	−0.0020 (12)
C4	0.0618 (16)	0.0768 (19)	0.0407 (13)	−0.0208 (14)	0.0261 (12)	−0.0115 (13)
C5	0.0357 (10)	0.0374 (11)	0.0386 (11)	−0.0018 (9)	0.0175 (9)	0.0019 (9)
C6	0.0557 (13)	0.0454 (13)	0.0373 (11)	−0.0035 (11)	0.0233 (10)	0.0020 (10)
N1	0.0476 (11)	0.0521 (12)	0.0452 (11)	−0.0138 (9)	0.0230 (9)	−0.0071 (9)
N2	0.0474 (11)	0.0397 (10)	0.0433 (10)	−0.0046 (8)	0.0260 (9)	0.0040 (8)
N3	0.0529 (12)	0.0441 (11)	0.0418 (10)	−0.0085 (9)	0.0201 (9)	−0.0025 (8)

Cl1—C1	1.728 (2)	C4—H4	0.9300
C1—N3	1.319 (3)	C5—N2	1.339 (3)
C1—C2	1.378 (3)	C5—N1	1.356 (3)
C2—C5	1.409 (3)	C6—N2	1.312 (3)
C2—C3	1.421 (3)	C6—N3	1.341 (3)
C3—C4	1.353 (4)	C6—H6	0.9300
C3—H3	0.9300	N2—H2	0.8600
C4—N1	1.376 (3)
N3—C1—C2	123.4 (2)	N2—C5—N1	126.6 (2)
N3—C1—Cl1	116.75 (18)	N2—C5—C2	124.9 (2)
C2—C1—Cl1	119.89 (17)	N1—C5—C2	108.5 (2)
C1—C2—C5	113.7 (2)	N2—C6—N3	127.6 (2)
C1—C2—C3	139.4 (2)	N2—C6—H6	116.2
C5—C2—C3	106.9 (2)	N3—C6—H6	116.2
C4—C3—C2	105.9 (2)	C5—N1—C4	107.4 (2)
C4—C3—H3	127.0	C6—N2—C5	113.9 (2)
C2—C3—H3	127.0	C6—N2—H2	123.0
C3—C4—N1	111.3 (2)	C5—N2—H2	123.0
C3—C4—H4	124.4	C1—N3—C6	116.5 (2)
N1—C4—H4	124.4
N3—C1—C2—C5	2.1 (4)	C3—C2—C5—N1	−0.2 (3)
Cl1—C1—C2—C5	−177.86 (17)	N2—C5—N1—C4	−179.5 (3)
N3—C1—C2—C3	−179.7 (3)	C2—C5—N1—C4	0.0 (3)
Cl1—C1—C2—C3	0.3 (4)	C3—C4—N1—C5	0.1 (4)
C1—C2—C3—C4	−178.0 (3)	N3—C6—N2—C5	0.8 (4)
C5—C2—C3—C4	0.3 (3)	N1—C5—N2—C6	180.0 (2)
C2—C3—C4—N1	−0.2 (4)	C2—C5—N2—C6	0.5 (3)
C1—C2—C5—N2	−1.9 (3)	C2—C1—N3—C6	−1.1 (4)
C3—C2—C5—N2	179.4 (2)	Cl1—C1—N3—C6	178.90 (18)
C1—C2—C5—N1	178.6 (2)	N2—C6—N3—C1	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.07	2.927 (3)	174
C6—H6···N3ii	0.93	2.57	3.315 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.07	2.927 (3)	174
C6—H6⋯N3ii	0.93	2.57	3.315 (3)	137

Symmetry codes: (i) ; (ii) .