7-Chloro-5-(chloro-meth-yl)pyrazolo-[1,5-a]pyrimidine-3-carbonitrile.

All non-H atoms of the title compound, C(8)H(4)Cl(2)N(4), are essentially coplanar, with an r.m.s. deviation of 0.011 Å. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into infinite sheets parallel to the bc plane.

Related literature

For details of the synthesis, see: Li et al. (2006 ▶). For applications of pyrazolo­[1,5-a]pyrimidines as pharmacophores or building blocks in anti-tumor drug design, see: Li et al. (2006 ▶); Di Grandi et al. (2009 ▶); Powell et al. (2007 ▶); Gopalsamy et al. (2005 ▶).

Experimental

Crystal data

C8H4Cl2N4

M = 227.05

Monoclinic,

a = 4.9817 (4) Å

b = 18.4025 (15) Å

c = 10.1526 (9) Å

β = 95.924 (1)°

V = 925.78 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 301 K

0.60 × 0.48 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.693, T max = 0.879

5429 measured reflections

2111 independent reflections

1749 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.04

2111 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S160053681201166X/im2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201166X/im2361Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201166X/im2361Isup3.cml

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

C8H4Cl2N4	F(000) = 456
Mr = 227.05	Dx = 1.629 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2237 reflections
a = 4.9817 (4) Å	θ = 3.9–27.6°
b = 18.4025 (15) Å	µ = 0.66 mm−1
c = 10.1526 (9) Å	T = 301 K
β = 95.924 (1)°	Block, red
V = 925.78 (13) Å3	0.60 × 0.48 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2111 independent reflections
Radiation source: fine-focus sealed tube	1749 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
phi and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
Tmin = 0.693, Tmax = 0.879	k = −13→23
5429 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.050P)2 + 0.3703P] where P = (Fo2 + 2Fc2)/3
2111 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.53 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	0.32935 (9)	0.26419 (3)	0.40816 (5)	0.04533 (17)
Cl2	0.73176 (14)	0.03358 (3)	0.13931 (8)	0.0784 (3)
N1	0.9223 (3)	0.23861 (8)	0.10690 (15)	0.0376 (3)
N2	1.2065 (4)	0.41634 (10)	−0.0585 (2)	0.0636 (5)
N3	0.5932 (4)	0.38077 (9)	0.26671 (18)	0.0503 (4)
N4	0.6551 (3)	0.31043 (8)	0.24035 (15)	0.0374 (3)
C1	0.5553 (4)	0.25052 (10)	0.29599 (18)	0.0363 (4)
C2	0.6391 (4)	0.18420 (10)	0.25839 (18)	0.0390 (4)
H2	0.5762	0.1420	0.2952	0.047*
C3	0.8249 (4)	0.18073 (10)	0.16175 (18)	0.0378 (4)
C4	0.9331 (5)	0.10975 (11)	0.1153 (2)	0.0554 (6)
H4A	1.1109	0.1018	0.1615	0.066*
H4B	0.9540	0.1138	0.0216	0.066*
C5	0.8380 (3)	0.30370 (10)	0.14617 (17)	0.0352 (4)
C6	0.8930 (4)	0.37484 (10)	0.11144 (19)	0.0423 (4)
C7	1.0677 (4)	0.39787 (10)	0.0175 (2)	0.0473 (5)
C8	0.7377 (5)	0.41835 (11)	0.1879 (2)	0.0520 (5)
H8	0.7362	0.4688	0.1837	0.062*

	U11	U22	U33	U12	U13	U23
Cl1	0.0409 (3)	0.0559 (3)	0.0418 (3)	−0.0012 (2)	0.01678 (19)	−0.0018 (2)
Cl2	0.0764 (4)	0.0456 (3)	0.1169 (6)	−0.0135 (3)	0.0270 (4)	−0.0184 (3)
N1	0.0376 (8)	0.0389 (8)	0.0378 (8)	0.0000 (6)	0.0108 (6)	0.0019 (6)
N2	0.0747 (13)	0.0502 (11)	0.0710 (13)	−0.0039 (10)	0.0321 (11)	0.0098 (10)
N3	0.0591 (11)	0.0374 (9)	0.0574 (10)	0.0019 (8)	0.0213 (8)	−0.0043 (8)
N4	0.0381 (8)	0.0379 (8)	0.0377 (8)	−0.0003 (6)	0.0110 (6)	−0.0009 (6)
C1	0.0323 (8)	0.0449 (10)	0.0328 (8)	−0.0023 (7)	0.0089 (7)	0.0012 (7)
C2	0.0403 (9)	0.0381 (10)	0.0398 (9)	−0.0032 (8)	0.0099 (8)	0.0035 (8)
C3	0.0403 (9)	0.0364 (9)	0.0376 (9)	−0.0009 (7)	0.0075 (7)	0.0007 (7)
C4	0.0654 (14)	0.0379 (11)	0.0676 (14)	0.0002 (10)	0.0292 (11)	−0.0003 (10)
C5	0.0333 (8)	0.0391 (9)	0.0341 (9)	−0.0023 (7)	0.0078 (7)	0.0007 (7)
C6	0.0458 (10)	0.0368 (10)	0.0458 (10)	−0.0045 (8)	0.0114 (8)	0.0033 (8)
C7	0.0549 (12)	0.0360 (10)	0.0527 (12)	−0.0045 (9)	0.0137 (10)	0.0047 (9)
C8	0.0621 (13)	0.0350 (10)	0.0612 (13)	−0.0022 (9)	0.0177 (11)	−0.0011 (9)

Cl1—C1	1.7006 (18)	C2—C3	1.418 (2)
Cl2—C4	1.755 (2)	C2—H2	0.9300
N1—C3	1.318 (2)	C3—C4	1.507 (3)
N1—C5	1.343 (2)	C4—H4A	0.9700
N2—C7	1.139 (3)	C4—H4B	0.9700
N3—C8	1.325 (3)	C5—C6	1.390 (3)
N3—N4	1.364 (2)	C6—C8	1.402 (3)
N4—C1	1.356 (2)	C6—C7	1.421 (3)
N4—C5	1.393 (2)	C8—H8	0.9300
C1—C2	1.357 (3)
C3—N1—C5	117.09 (15)	C3—C4—H4A	108.6
C8—N3—N4	103.25 (16)	Cl2—C4—H4A	108.6
C1—N4—N3	126.15 (15)	C3—C4—H4B	108.6
C1—N4—C5	120.50 (15)	Cl2—C4—H4B	108.6
N3—N4—C5	113.35 (15)	H4A—C4—H4B	107.5
N4—C1—C2	118.49 (16)	N1—C5—C6	133.52 (16)
N4—C1—Cl1	117.07 (14)	N1—C5—N4	121.99 (15)
C2—C1—Cl1	124.44 (14)	C6—C5—N4	104.50 (15)
C1—C2—C3	118.48 (16)	C5—C6—C8	105.24 (17)
C1—C2—H2	120.8	C5—C6—C7	126.97 (18)
C3—C2—H2	120.8	C8—C6—C7	127.79 (19)
N1—C3—C2	123.45 (17)	N2—C7—C6	179.6 (3)
N1—C3—C4	114.14 (16)	N3—C8—C6	113.67 (19)
C2—C3—C4	122.40 (16)	N3—C8—H8	123.2
C3—C4—Cl2	114.86 (15)	C6—C8—H8	123.2
C8—N3—N4—C1	−179.43 (19)	C3—N1—C5—C6	−179.6 (2)
C8—N3—N4—C5	0.3 (2)	C3—N1—C5—N4	−0.2 (3)
N3—N4—C1—C2	−179.90 (18)	C1—N4—C5—N1	0.0 (3)
C5—N4—C1—C2	0.4 (3)	N3—N4—C5—N1	−179.71 (17)
N3—N4—C1—Cl1	0.6 (3)	C1—N4—C5—C6	179.58 (16)
C5—N4—C1—Cl1	−179.05 (13)	N3—N4—C5—C6	−0.1 (2)
N4—C1—C2—C3	−0.6 (3)	N1—C5—C6—C8	179.4 (2)
Cl1—C1—C2—C3	178.78 (14)	N4—C5—C6—C8	0.0 (2)
C5—N1—C3—C2	−0.1 (3)	N1—C5—C6—C7	0.0 (4)
C5—N1—C3—C4	−178.66 (18)	N4—C5—C6—C7	−179.5 (2)
C1—C2—C3—N1	0.5 (3)	N4—N3—C8—C6	−0.3 (3)
C1—C2—C3—C4	178.98 (19)	C5—C6—C8—N3	0.2 (3)
N1—C3—C4—Cl2	−159.03 (16)	C7—C6—C8—N3	179.7 (2)
C2—C3—C4—Cl2	22.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2i	0.93	2.50	3.337 (3)	150
C2—H2···N2ii	0.93	2.70	3.515 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N2i	0.93	2.50	3.337 (3)	150
C2—H2⋯N2ii	0.93	2.70	3.515 (3)	146

Symmetry codes: (i) ; (ii) .