1-(2-Chloro-eth-yl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one.

In the title compound, C(7)H(7)ClN(4)O, the pyrazolo-pyrimidine ring is essentially planar, the r.m.s. deviation of the fitted atoms being 0.0071 Å. The crystal structure features strong N-H⋯O hydrogen bonds and further consolidated by weak C-H⋯O, C-H⋯N and C-H⋯Cl inter-actions.

Related literature

For the biological activity of pyrazolo­pyrimidines, see: Carraro et al. (2006 ▶). For a related structure, see: Dolzhenko et al. (2009 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H7ClN4O

M = 198.61

Monoclinic,

a = 4.6448 (1) Å

b = 8.0792 (1) Å

c = 22.7335 (4) Å

β = 93.554 (1)°

V = 851.46 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.930, T max = 0.937

7660 measured reflections

1548 independent reflections

1353 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 0.87

1548 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025184/pv2552sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025184/pv2552Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025184/pv2552Isup3.cml

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

C7H7ClN4O	F(000) = 416
Mr = 198.61	Dx = 1.565 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1548 reflections
a = 4.6448 (1) Å	θ = 1.8–25.2°
b = 8.0792 (1) Å	µ = 0.41 mm−1
c = 22.7335 (4) Å	T = 296 K
β = 93.554 (1)°	Block, yellow
V = 851.46 (3) Å3	0.18 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	1548 independent reflections
Radiation source: fine-focus sealed tube	1353 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→5
Tmin = 0.930, Tmax = 0.937	k = −9→9
7660 measured reflections	l = −27→25

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.5291P] where P = (Fo2 + 2Fc2)/3
1548 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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
Cl1	0.89765 (12)	0.64259 (8)	0.72864 (2)	0.0600 (2)
O1	0.5103 (3)	0.78930 (17)	0.99906 (6)	0.0516 (4)
N1	0.7733 (3)	0.95763 (18)	0.94256 (6)	0.0381 (4)
H1	0.7021	1.0429	0.9590	0.046*
N2	1.0887 (3)	0.86963 (19)	0.87124 (7)	0.0396 (4)
N3	1.0967 (3)	0.57267 (18)	0.86397 (6)	0.0376 (4)
N4	0.9763 (3)	0.43809 (19)	0.88974 (7)	0.0434 (4)
C5	0.9640 (4)	0.9842 (2)	0.90068 (8)	0.0401 (4)
H5A	1.0092	1.0935	0.8924	0.048*
C6	1.0057 (4)	0.7151 (2)	0.88711 (7)	0.0331 (4)
C1	1.2904 (4)	0.5504 (3)	0.81692 (8)	0.0418 (4)
H1A	1.4385	0.4711	0.8295	0.050*
H1B	1.3848	0.6548	0.8096	0.050*
C2	1.1398 (4)	0.4907 (2)	0.76054 (8)	0.0442 (5)
H2A	1.0330	0.3907	0.7683	0.053*
H2B	1.2826	0.4635	0.7327	0.053*
C4	0.6848 (4)	0.8026 (2)	0.96076 (7)	0.0371 (4)
C7	0.8174 (4)	0.6729 (2)	0.92974 (7)	0.0349 (4)
C3	0.8092 (4)	0.4993 (2)	0.92932 (8)	0.0424 (4)
H3	0.7002	0.4356	0.9538	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0545 (3)	0.0640 (4)	0.0607 (4)	0.0019 (2)	−0.0027 (3)	0.0011 (3)
O1	0.0692 (9)	0.0403 (8)	0.0488 (8)	−0.0011 (6)	0.0335 (7)	−0.0006 (6)
N1	0.0486 (8)	0.0314 (8)	0.0355 (8)	0.0000 (6)	0.0122 (6)	−0.0036 (6)
N2	0.0475 (9)	0.0357 (8)	0.0370 (8)	−0.0044 (7)	0.0137 (7)	−0.0006 (6)
N3	0.0437 (8)	0.0351 (8)	0.0354 (8)	0.0002 (6)	0.0121 (6)	−0.0014 (6)
N4	0.0550 (9)	0.0326 (8)	0.0436 (9)	0.0000 (7)	0.0117 (7)	0.0026 (7)
C5	0.0489 (10)	0.0352 (10)	0.0372 (9)	−0.0061 (8)	0.0098 (8)	0.0021 (8)
C6	0.0360 (9)	0.0343 (9)	0.0295 (8)	−0.0008 (7)	0.0060 (7)	−0.0005 (7)
C1	0.0397 (9)	0.0451 (11)	0.0418 (10)	0.0050 (8)	0.0132 (8)	−0.0037 (8)
C2	0.0505 (11)	0.0395 (11)	0.0442 (10)	0.0004 (8)	0.0159 (8)	−0.0060 (8)
C4	0.0452 (10)	0.0365 (10)	0.0304 (9)	−0.0030 (8)	0.0088 (7)	−0.0002 (7)
C7	0.0413 (9)	0.0347 (9)	0.0293 (8)	−0.0019 (7)	0.0076 (7)	0.0006 (7)
C3	0.0528 (11)	0.0364 (10)	0.0393 (10)	−0.0025 (8)	0.0141 (8)	0.0033 (8)

Cl1—C2	1.788 (2)	C5—H5A	0.9300
O1—C4	1.231 (2)	C6—C7	1.388 (2)
N1—C5	1.357 (2)	C1—C2	1.501 (3)
N1—C4	1.389 (2)	C1—H1A	0.9700
N1—H1	0.8600	C1—H1B	0.9700
N2—C5	1.299 (2)	C2—H2A	0.9700
N2—C6	1.362 (2)	C2—H2B	0.9700
N3—C6	1.344 (2)	C4—C7	1.424 (2)
N3—N4	1.371 (2)	C7—C3	1.403 (3)
N3—C1	1.451 (2)	C3—H3	0.9300
N4—C3	1.320 (2)
C5—N1—C4	124.71 (15)	C2—C1—H1B	109.0
C5—N1—H1	117.6	H1A—C1—H1B	107.8
C4—N1—H1	117.6	C1—C2—Cl1	112.00 (14)
C5—N2—C6	111.97 (15)	C1—C2—H2A	109.2
C6—N3—N4	111.42 (13)	Cl1—C2—H2A	109.2
C6—N3—C1	128.26 (15)	C1—C2—H2B	109.2
N4—N3—C1	120.30 (15)	Cl1—C2—H2B	109.2
C3—N4—N3	105.48 (15)	H2A—C2—H2B	107.9
N2—C5—N1	125.45 (17)	O1—C4—N1	120.63 (16)
N2—C5—H5A	117.3	O1—C4—C7	127.58 (17)
N1—C5—H5A	117.3	N1—C4—C7	111.79 (14)
N3—C6—N2	125.45 (15)	C6—C7—C3	105.00 (16)
N3—C6—C7	106.86 (15)	C6—C7—C4	118.38 (16)
N2—C6—C7	127.68 (16)	C3—C7—C4	136.61 (17)
N3—C1—C2	113.08 (15)	N4—C3—C7	111.23 (16)
N3—C1—H1A	109.0	N4—C3—H3	124.4
C2—C1—H1A	109.0	C7—C3—H3	124.4
N3—C1—H1B	109.0
C6—N3—N4—C3	−0.1 (2)	C5—N1—C4—O1	−179.89 (18)
C1—N3—N4—C3	−178.72 (16)	C5—N1—C4—C7	−0.4 (2)
C6—N2—C5—N1	0.1 (3)	N3—C6—C7—C3	0.2 (2)
C4—N1—C5—N2	0.7 (3)	N2—C6—C7—C3	−179.13 (18)
N4—N3—C6—N2	179.28 (17)	N3—C6—C7—C4	−179.02 (15)
C1—N3—C6—N2	−2.2 (3)	N2—C6—C7—C4	1.6 (3)
N4—N3—C6—C7	−0.1 (2)	O1—C4—C7—C6	178.81 (19)
C1—N3—C6—C7	178.40 (17)	N1—C4—C7—C6	−0.6 (2)
C5—N2—C6—N3	179.47 (17)	O1—C4—C7—C3	−0.1 (4)
C5—N2—C6—C7	−1.3 (3)	N1—C4—C7—C3	−179.6 (2)
C6—N3—C1—C2	−108.1 (2)	N3—N4—C3—C7	0.2 (2)
N4—N3—C1—C2	70.3 (2)	C6—C7—C3—N4	−0.3 (2)
N3—C1—C2—Cl1	66.78 (19)	C4—C7—C3—N4	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.96	2.810 (2)	170
C5—H5A···N4ii	0.93	2.79	3.676 (2)	160
C2—H2A···Cl1iii	0.97	2.84	3.779 (2)	164
C2—H2B···N2iv	0.97	2.59	3.463 (2)	150
C3—H3···O1v	0.93	2.35	3.254 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.96	2.810 (2)	170
C5—H5A⋯N4ii	0.93	2.79	3.676 (2)	160
C2—H2A⋯Cl1iii	0.97	2.84	3.779 (2)	164
C2—H2B⋯N2iv	0.97	2.59	3.463 (2)	150
C3—H3⋯O1v	0.93	2.35	3.254 (2)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .