2-Chloro-9-isopropyl-N,N-dimethyl-9H-purin-6-amine.

In the title compound, C(10)H(14)ClN(5), the imidazole and pyrimidine rings are essentially planar [maximum deviation = 0.0013 (14) and 0.0207 (13) Å, respectively]. In the crystal, the mol-ecules are linked by weak C-H⋯N inter-actions into chains parallel to the c axis and the crystal packing is stabilized by additional weak C-H⋯N and C-H⋯Cl inter-actions.

Related literature

The title compound was prepared according to a modification of the procedure of Fiorini & Abel (1998 ▶). For the synthesis and/or biological activity of related compounds, see: Legraverend & Grierson (2006 ▶). For related structures, see: Kubicki & Codding (2001 ▶); Trávníček & Popa (2007 ▶); Rouchal et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C10H14ClN5

M = 239.71

Monoclinic,

a = 12.0483 (3) Å

b = 8.7689 (2) Å

c = 11.5538 (3) Å

β = 109.965 (3)°

V = 1147.30 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 120 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2 large Be window) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.968, T max = 1.000

13393 measured reflections

2022 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.068

S = 1.05

2022 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablocks global, I. DOI: 10.1107/S1600536810011797/pk2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011797/pk2238Isup2.hkl

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

C10H14ClN5	F(000) = 504
Mr = 239.71	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Melting point = 422–418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.7107 Å
a = 12.0483 (3) Å	Cell parameters from 8720 reflections
b = 8.7689 (2) Å	θ = 2.9–27.3°
c = 11.5538 (3) Å	µ = 0.31 mm−1
β = 109.965 (3)°	T = 120 K
V = 1147.30 (5) Å3	Block, colourless
Z = 4	0.40 × 0.40 × 0.30 mm

Oxford Diffraction Xcalibur (Sapphire2 large Be window) diffractometer	2022 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1798 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 8.4 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −14→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −9→10
Tmin = 0.968, Tmax = 1.000	l = −13→13
13393 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0355P)2 + 0.4207P] where P = (Fo2 + 2Fc2)/3
2022 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction Ltd, 2009). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.78721 (3)	0.18146 (4)	0.33908 (3)	0.02432 (12)
N1	0.80758 (9)	−0.04481 (12)	0.48883 (9)	0.0166 (2)
N2	0.67313 (9)	0.15775 (12)	0.49228 (10)	0.0179 (3)
N3	0.69089 (10)	−0.14494 (13)	0.72589 (10)	0.0225 (3)
N4	0.82037 (10)	−0.23853 (13)	0.64258 (10)	0.0184 (3)
N5	0.55582 (10)	0.16106 (13)	0.61327 (10)	0.0197 (3)
C1	0.75175 (11)	0.08580 (15)	0.45552 (11)	0.0168 (3)
C2	0.63956 (11)	0.09009 (15)	0.58130 (11)	0.0169 (3)
C3	0.69562 (11)	−0.04950 (15)	0.63134 (11)	0.0167 (3)
C4	0.76612 (12)	−0.25408 (16)	0.72857 (13)	0.0229 (3)
H4A	0.7816	−0.3366	0.7851	0.027*
C5	0.77572 (11)	−0.10713 (15)	0.57988 (11)	0.0157 (3)
C6	0.51096 (13)	0.30962 (16)	0.56040 (14)	0.0256 (3)
H6A	0.4933	0.3068	0.4711	0.038*
H6B	0.5707	0.3880	0.5968	0.038*
H6C	0.4388	0.3337	0.5778	0.038*
C7	0.51768 (12)	0.10497 (17)	0.71274 (13)	0.0248 (3)
H7A	0.5191	−0.0068	0.7134	0.037*
H7B	0.4372	0.1406	0.6998	0.037*
H7C	0.5711	0.1435	0.7917	0.037*
C8	0.90697 (12)	−0.34193 (16)	0.61883 (13)	0.0214 (3)
H8A	0.9468	−0.2849	0.5691	0.026*
C9	0.84438 (14)	−0.47859 (18)	0.54375 (14)	0.0314 (4)
H9A	0.7866	−0.4433	0.4660	0.047*
H9B	0.8038	−0.5358	0.5904	0.047*
H9C	0.9024	−0.5447	0.5265	0.047*
C10	1.00104 (13)	−0.38877 (18)	0.73954 (14)	0.0294 (3)
H10A	1.0359	−0.2974	0.7868	0.044*
H10B	1.0627	−0.4476	0.7221	0.044*
H10C	0.9650	−0.4515	0.7874	0.044*

	U11	U22	U33	U12	U13	U23
Cl1	0.0311 (2)	0.0225 (2)	0.02385 (19)	0.00422 (14)	0.01520 (15)	0.00769 (13)
N1	0.0180 (5)	0.0170 (6)	0.0149 (5)	−0.0002 (4)	0.0058 (4)	0.0005 (4)
N2	0.0189 (6)	0.0173 (6)	0.0176 (5)	0.0002 (4)	0.0062 (4)	−0.0005 (4)
N3	0.0256 (6)	0.0227 (6)	0.0219 (6)	0.0007 (5)	0.0115 (5)	0.0038 (5)
N4	0.0198 (6)	0.0168 (6)	0.0189 (6)	0.0020 (4)	0.0071 (5)	0.0037 (5)
N5	0.0196 (6)	0.0200 (6)	0.0204 (6)	0.0021 (5)	0.0081 (5)	−0.0020 (5)
C1	0.0192 (7)	0.0170 (7)	0.0136 (6)	−0.0023 (5)	0.0046 (5)	−0.0003 (5)
C2	0.0162 (6)	0.0174 (7)	0.0152 (6)	−0.0031 (5)	0.0031 (5)	−0.0048 (5)
C3	0.0169 (6)	0.0174 (7)	0.0155 (6)	−0.0025 (5)	0.0049 (5)	−0.0019 (5)
C4	0.0267 (7)	0.0221 (8)	0.0219 (7)	0.0014 (6)	0.0109 (6)	0.0067 (6)
C5	0.0149 (6)	0.0153 (7)	0.0149 (6)	−0.0017 (5)	0.0025 (5)	−0.0016 (5)
C6	0.0264 (7)	0.0228 (8)	0.0280 (8)	0.0070 (6)	0.0097 (6)	−0.0013 (6)
C7	0.0231 (7)	0.0284 (8)	0.0276 (7)	−0.0006 (6)	0.0148 (6)	−0.0038 (6)
C8	0.0202 (7)	0.0212 (7)	0.0250 (7)	0.0051 (6)	0.0105 (6)	0.0055 (6)
C9	0.0347 (9)	0.0262 (8)	0.0329 (8)	0.0061 (7)	0.0110 (7)	−0.0036 (7)
C10	0.0225 (7)	0.0306 (8)	0.0326 (8)	0.0044 (6)	0.0064 (6)	0.0094 (7)

Cl1—C1	1.7575 (13)	C6—H6A	0.9800
N1—C1	1.3174 (17)	C6—H6B	0.9800
N1—C5	1.3522 (17)	C6—H6C	0.9800
N2—C1	1.3230 (17)	C7—H7A	0.9800
N2—C2	1.3630 (17)	C7—H7B	0.9800
N3—C4	1.3112 (18)	C7—H7C	0.9800
N3—C3	1.3926 (17)	C8—C9	1.520 (2)
N4—C5	1.3696 (17)	C8—C10	1.5228 (19)
N4—C4	1.3698 (18)	C8—H8A	1.0000
N4—C8	1.4769 (17)	C9—H9A	0.9800
N5—C2	1.3402 (17)	C9—H9B	0.9800
N5—C7	1.4610 (18)	C9—H9C	0.9800
N5—C6	1.4618 (18)	C10—H10A	0.9800
C2—C3	1.4220 (19)	C10—H10B	0.9800
C3—C5	1.3900 (18)	C10—H10C	0.9800
C4—H4A	0.9500
C1—N1—C5	109.04 (11)	N5—C6—H6C	109.5
C1—N2—C2	117.66 (11)	H6A—C6—H6C	109.5
C4—N3—C3	104.13 (11)	H6B—C6—H6C	109.5
C5—N4—C4	105.59 (11)	N5—C7—H7A	109.5
C5—N4—C8	126.37 (11)	N5—C7—H7B	109.5
C4—N4—C8	128.02 (11)	H7A—C7—H7B	109.5
C2—N5—C7	121.94 (11)	N5—C7—H7C	109.5
C2—N5—C6	120.29 (11)	H7A—C7—H7C	109.5
C7—N5—C6	117.26 (11)	H7B—C7—H7C	109.5
N1—C1—N2	132.14 (12)	N4—C8—C9	110.23 (11)
N1—C1—Cl1	113.90 (10)	N4—C8—C10	110.34 (11)
N2—C1—Cl1	113.95 (10)	C9—C8—C10	112.28 (12)
N5—C2—N2	116.82 (12)	N4—C8—H8A	107.9
N5—C2—C3	125.83 (12)	C9—C8—H8A	107.9
N2—C2—C3	117.35 (11)	C10—C8—H8A	107.9
C5—C3—N3	109.72 (11)	C8—C9—H9A	109.5
C5—C3—C2	116.22 (12)	C8—C9—H9B	109.5
N3—C3—C2	134.05 (12)	H9A—C9—H9B	109.5
N3—C4—N4	114.04 (12)	C8—C9—H9C	109.5
N3—C4—H4A	123.0	H9A—C9—H9C	109.5
N4—C4—H4A	123.0	H9B—C9—H9C	109.5
N1—C5—N4	125.94 (12)	C8—C10—H10A	109.5
N1—C5—C3	127.51 (12)	C8—C10—H10B	109.5
N4—C5—C3	106.52 (11)	H10A—C10—H10B	109.5
N5—C6—H6A	109.5	C8—C10—H10C	109.5
N5—C6—H6B	109.5	H10A—C10—H10C	109.5
H6A—C6—H6B	109.5	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N1i	0.95	2.49	3.3728 (18)	154
C7—H7C···Cl1ii	0.98	2.91	3.5981 (14)	128
C7—H7B···N3iii	0.98	2.75	3.584 (2)	143
C9—H9A···N3iv	0.98	2.73	3.6664 (18)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N1i	0.95	2.49	3.3728 (18)	154
C7—H7C⋯Cl1ii	0.98	2.91	3.5981 (14)	128
C7—H7B⋯N3iii	0.98	2.75	3.584 (2)	143
C9—H9A⋯N3iv	0.98	2.73	3.6664 (18)	161

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