2,6-Dichloro-7-isopropyl-7H-purine.

In the title mol-ecule, C(8)H(8)Cl(2)N(4), the essentially planar imidazole and pyrimidine rings [maximum deviations of 0.0030 (15) and 0.0111 (15) Å, respectively] make a dihedral angle of 1.32 (8)°. In the crystal, the fused-ring systems are stacked approximately parallel to the bc plane, with a centroid-centroid distance between inversion-related pyrimidine rings of 3.5189 (9) Å.

Related literature

For the synthesis, see: Oumata et al. (2008 ▶). For biological activity of some purine derivatives, see: Legraverend & Grierson (2006 ▶). For the selective synthesis of N7-substituted purines, see: Kotek et al. (2010 ▶). For related structures, see: Rouchal et al. (2009a ▶,b ▶, 2010 ▶).

Experimental

Crystal data

C8H8Cl2N4

M = 231.08

Triclinic,

a = 7.0146 (5) Å

b = 8.2862 (6) Å

c = 8.9686 (7) Å

α = 70.499 (7)°

β = 83.820 (6)°

γ = 74.204 (6)°

V = 472.75 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.65 mm−1

T = 120 K

0.40 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.933, T max = 1.000

2825 measured reflections

1656 independent reflections

1419 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.061

S = 1.05

1656 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201879X/lh5458sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201879X/lh5458Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201879X/lh5458Isup3.cml

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

C8H8Cl2N4	Z = 2
Mr = 231.08	F(000) = 236
Triclinic, P1	Dx = 1.623 Mg m−3
Hall symbol: -P 1	Melting point: 426 K
a = 7.0146 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2862 (6) Å	Cell parameters from 2034 reflections
c = 8.9686 (7) Å	θ = 3.0–27.7°
α = 70.499 (7)°	µ = 0.65 mm−1
β = 83.820 (6)°	T = 120 K
γ = 74.204 (6)°	Block, colourless
V = 472.75 (7) Å3	0.40 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur Sapphire2 diffractometer	1656 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1419 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.933, Tmax = 1.000	l = −10→10
2825 measured reflections

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.0416P] where P = (Fo2 + 2Fc2)/3
1656 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 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 > 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	0.22677 (6)	0.42378 (6)	−0.21906 (5)	0.02126 (13)
Cl2	0.31193 (6)	0.39565 (5)	0.35468 (5)	0.02020 (13)
N1	0.2261 (2)	0.71202 (18)	−0.16073 (15)	0.0172 (3)
N2	0.26395 (19)	0.44137 (17)	0.05831 (15)	0.0160 (3)
N3	0.27132 (19)	0.83054 (17)	0.17303 (15)	0.0150 (3)
N4	0.2361 (2)	0.96725 (18)	−0.09060 (15)	0.0175 (3)
C1	0.2390 (2)	0.5421 (2)	−0.09346 (19)	0.0160 (4)
C2	0.2758 (2)	0.5246 (2)	0.15927 (18)	0.0153 (4)
C3	0.2616 (2)	0.7041 (2)	0.10815 (18)	0.0139 (3)
C4	0.2541 (2)	0.9822 (2)	0.04869 (19)	0.0177 (4)
H4	0.2549	1.0914	0.0613	0.021*
C5	0.2397 (2)	0.7924 (2)	−0.05616 (18)	0.0153 (4)
C6	0.2741 (2)	0.8107 (2)	0.34377 (18)	0.0165 (4)
H6	0.3683	0.6952	0.3972	0.020*
C7	0.3474 (3)	0.9569 (2)	0.3651 (2)	0.0245 (4)
H7A	0.4765	0.9589	0.3115	0.037*
H7B	0.3608	0.9358	0.4782	0.037*
H7C	0.2525	1.0708	0.3195	0.037*
C8	0.0694 (2)	0.8061 (2)	0.41748 (19)	0.0203 (4)
H8A	−0.0253	0.9186	0.3670	0.030*
H8B	0.0733	0.7879	0.5310	0.030*
H8C	0.0282	0.7090	0.4020	0.030*

	U11	U22	U33	U12	U13	U23
Cl1	0.0217 (2)	0.0247 (2)	0.0217 (2)	−0.00501 (18)	−0.00236 (17)	−0.01289 (18)
Cl2	0.0284 (3)	0.0158 (2)	0.0155 (2)	−0.00685 (18)	−0.00177 (17)	−0.00235 (17)
N1	0.0152 (7)	0.0196 (8)	0.0164 (7)	−0.0033 (6)	−0.0005 (6)	−0.0062 (6)
N2	0.0136 (7)	0.0170 (8)	0.0182 (7)	−0.0040 (6)	−0.0006 (6)	−0.0064 (6)
N3	0.0158 (7)	0.0140 (7)	0.0155 (7)	−0.0047 (6)	−0.0004 (6)	−0.0041 (6)
N4	0.0188 (8)	0.0152 (8)	0.0177 (7)	−0.0045 (6)	−0.0003 (6)	−0.0038 (6)
C1	0.0109 (8)	0.0211 (9)	0.0188 (8)	−0.0034 (7)	0.0003 (7)	−0.0105 (7)
C2	0.0109 (8)	0.0182 (9)	0.0152 (8)	−0.0035 (7)	0.0004 (6)	−0.0036 (7)
C3	0.0094 (8)	0.0166 (9)	0.0162 (8)	−0.0030 (7)	0.0005 (6)	−0.0062 (7)
C4	0.0161 (9)	0.0137 (8)	0.0220 (9)	−0.0045 (7)	−0.0003 (7)	−0.0038 (7)
C5	0.0103 (8)	0.0184 (9)	0.0162 (8)	−0.0030 (7)	0.0005 (6)	−0.0050 (7)
C6	0.0185 (9)	0.0166 (9)	0.0145 (8)	−0.0036 (7)	−0.0017 (7)	−0.0053 (7)
C7	0.0301 (11)	0.0255 (10)	0.0230 (9)	−0.0119 (8)	−0.0007 (8)	−0.0104 (8)
C8	0.0227 (10)	0.0233 (10)	0.0159 (8)	−0.0066 (8)	0.0016 (7)	−0.0077 (7)

Cl1—C1	1.7437 (16)	C3—C5	1.414 (2)
Cl2—C2	1.7249 (16)	C4—H4	0.9500
N1—C1	1.315 (2)	C6—C7	1.511 (2)
N1—C5	1.343 (2)	C6—C8	1.519 (2)
N2—C2	1.3289 (19)	C6—H6	1.0000
N2—C1	1.339 (2)	C7—H7A	0.9800
N3—C4	1.360 (2)	C7—H7B	0.9800
N3—C3	1.3770 (19)	C7—H7C	0.9800
N3—C6	1.486 (2)	C8—H8A	0.9800
N4—C4	1.318 (2)	C8—H8B	0.9800
N4—C5	1.371 (2)	C8—H8C	0.9800
C2—C3	1.381 (2)
C1—N1—C5	112.46 (14)	N4—C5—C3	110.38 (14)
C2—N2—C1	115.85 (14)	N3—C6—C7	110.35 (13)
C4—N3—C3	105.08 (13)	N3—C6—C8	109.77 (12)
C4—N3—C6	127.26 (14)	C7—C6—C8	112.12 (14)
C3—N3—C6	127.25 (13)	N3—C6—H6	108.2
C4—N4—C5	103.55 (13)	C7—C6—H6	108.2
N1—C1—N2	130.38 (15)	C8—C6—H6	108.2
N1—C1—Cl1	116.32 (12)	C6—C7—H7A	109.5
N2—C1—Cl1	113.29 (12)	C6—C7—H7B	109.5
N2—C2—C3	121.08 (14)	H7A—C7—H7B	109.5
N2—C2—Cl2	116.30 (12)	C6—C7—H7C	109.5
C3—C2—Cl2	122.62 (13)	H7A—C7—H7C	109.5
N3—C3—C2	137.57 (15)	H7B—C7—H7C	109.5
N3—C3—C5	105.65 (13)	C6—C8—H8A	109.5
C2—C3—C5	116.70 (15)	C6—C8—H8B	109.5
N4—C4—N3	115.34 (15)	H8A—C8—H8B	109.5
N4—C4—H4	122.3	C6—C8—H8C	109.5
N3—C4—H4	122.3	H8A—C8—H8C	109.5
N1—C5—N4	126.13 (14)	H8B—C8—H8C	109.5
N1—C5—C3	123.49 (15)