2-Chloro-6-[(2,4-dimeth-oxy-benz-yl)amino]-9-isopropyl-9H-purine.

In the title compound, C17H20ClN5O2, the benzene ring and the purine ring system make a dihedral angle of 78.56 (4)°. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers. C-H⋯O and C-H⋯Cl contacts further link the mol-ecules, forming a three-dimensional network.

Related literature

For the synthesis, see: Oh et al. (1999 ▶). For related structures, see: Trávníček & Popa (2007a ▶,b ▶); Trávníček et al. (2010 ▶); Čajan & Trávníček (2011 ▶). For the cytotoxic activity of related compounds, see: Benson et al. (2005 ▶); Meijer et al. (1997 ▶); Štarha et al. (2010 ▶); Vrzal et al. (2010 ▶).

Experimental

Crystal data

C17H20ClN5O2

M = 361.83

Triclinic,

a = 7.8620 (2) Å

b = 9.20164 (18) Å

c = 13.3027 (3) Å

α = 82.4472 (18)°

β = 74.803 (2)°

γ = 66.012 (2)°

V = 848.16 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.908, T max = 0.930

7228 measured reflections

2965 independent reflections

2704 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.10

2965 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004121/ng5316sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004121/ng5316Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004121/ng5316Isup3.cml

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

C17H20ClN5O2	Z = 2
Mr = 361.83	F(000) = 380
Triclinic, P1	Dx = 1.417 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8620 (2) Å	Cell parameters from 7872 reflections
b = 9.20164 (18) Å	θ = 3.0–31.9°
c = 13.3027 (3) Å	µ = 0.25 mm−1
α = 82.4472 (18)°	T = 100 K
β = 74.803 (2)°	Prism, colourless
γ = 66.012 (2)°	0.40 × 0.35 × 0.30 mm
V = 848.16 (3) Å3

Agilent Xcalibur Sapphire2 diffractometer	2965 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2704 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.009
Detector resolution: 8.3611 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→8
Tmin = 0.908, Tmax = 0.930	l = −15→15
7228 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3
2965 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.19 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	0.70269 (5)	1.09303 (4)	0.25218 (2)	0.02037 (12)
O1	0.32700 (14)	0.87203 (11)	0.09283 (7)	0.0211 (2)
O2	0.83383 (14)	0.47675 (11)	−0.12752 (7)	0.0219 (2)
N1	0.58970 (15)	0.86255 (13)	0.31864 (8)	0.0154 (2)
N3	0.75392 (16)	0.92987 (13)	0.42340 (8)	0.0158 (2)
N6	0.48258 (16)	0.65791 (13)	0.35975 (8)	0.0157 (2)
H6	0.4819	0.5716	0.3970	0.019*
N7	0.63884 (16)	0.60705 (13)	0.55906 (8)	0.0164 (2)
N9	0.77924 (15)	0.76630 (13)	0.58170 (8)	0.0149 (2)
C2	0.67876 (18)	0.94292 (15)	0.34373 (10)	0.0151 (3)
C4	0.72769 (18)	0.81144 (15)	0.48852 (10)	0.0143 (3)
C5	0.64099 (18)	0.71309 (15)	0.47514 (10)	0.0145 (3)
C6	0.56932 (18)	0.74185 (15)	0.38453 (10)	0.0142 (3)
C8	0.72325 (19)	0.64331 (15)	0.62003 (10)	0.0170 (3)
H8	0.7432	0.5891	0.6844	0.020*
C9	0.38927 (19)	0.70512 (16)	0.27300 (10)	0.0157 (3)
H9A	0.3342	0.8228	0.2670	0.019*
H9B	0.2820	0.6692	0.2888	0.019*
C10	0.51862 (18)	0.64023 (15)	0.16885 (10)	0.0148 (3)
C11	0.47845 (18)	0.72793 (15)	0.07743 (10)	0.0156 (3)
C12	0.58604 (19)	0.67038 (16)	−0.01979 (10)	0.0171 (3)
H12	0.5559	0.7309	−0.0809	0.021*
C13	0.73911 (19)	0.52284 (16)	−0.02749 (10)	0.0173 (3)
C14	0.7841 (2)	0.43487 (16)	0.06153 (11)	0.0187 (3)
H14	0.8896	0.3352	0.0566	0.022*
C15	0.67172 (19)	0.49520 (15)	0.15851 (10)	0.0178 (3)
H15	0.7016	0.4343	0.2196	0.021*
C16	0.2745 (2)	0.96545 (17)	0.00354 (11)	0.0259 (3)
H16A	0.3842	0.9866	−0.0399	0.039*
H16B	0.1682	1.0665	0.0256	0.039*
H16C	0.2350	0.9077	−0.0367	0.039*
C17	0.9907 (2)	0.32597 (17)	−0.14131 (12)	0.0253 (3)
H17A	1.0488	0.3093	−0.2158	0.038*
H17B	0.9447	0.2416	−0.1120	0.038*
H17C	1.0861	0.3235	−0.1056	0.038*
C18	0.89162 (19)	0.83166 (15)	0.62220 (10)	0.0161 (3)
H18	0.8547	0.9460	0.5990	0.019*
C19	0.8456 (2)	0.82494 (17)	0.74010 (10)	0.0199 (3)
H19A	0.8871	0.7136	0.7649	0.030*
H19B	0.7073	0.8793	0.7669	0.030*
H19C	0.9125	0.8776	0.7649	0.030*
C20	1.1021 (2)	0.74454 (19)	0.57366 (12)	0.0267 (3)
H20A	1.1445	0.6337	0.5995	0.040*
H20B	1.1762	0.7962	0.5925	0.040*
H20C	1.1219	0.7474	0.4977	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0287 (2)	0.02086 (19)	0.01726 (18)	−0.01511 (15)	−0.00878 (14)	0.00570 (13)
O1	0.0227 (5)	0.0188 (5)	0.0140 (5)	0.0003 (4)	−0.0057 (4)	0.0005 (4)
O2	0.0223 (5)	0.0198 (5)	0.0176 (5)	−0.0041 (4)	0.0001 (4)	−0.0037 (4)
N1	0.0163 (5)	0.0155 (6)	0.0139 (5)	−0.0065 (5)	−0.0019 (4)	−0.0005 (4)
N3	0.0176 (6)	0.0145 (5)	0.0153 (6)	−0.0066 (5)	−0.0037 (4)	0.0000 (4)
N6	0.0220 (6)	0.0169 (6)	0.0122 (5)	−0.0109 (5)	−0.0061 (5)	0.0024 (4)
N7	0.0208 (6)	0.0163 (6)	0.0131 (5)	−0.0085 (5)	−0.0038 (4)	0.0003 (4)
N9	0.0184 (6)	0.0153 (5)	0.0130 (5)	−0.0078 (5)	−0.0050 (4)	−0.0005 (4)
C2	0.0158 (6)	0.0134 (6)	0.0139 (6)	−0.0049 (5)	−0.0012 (5)	−0.0003 (5)
C4	0.0141 (6)	0.0132 (6)	0.0127 (6)	−0.0031 (5)	−0.0012 (5)	−0.0022 (5)
C5	0.0144 (6)	0.0145 (6)	0.0134 (6)	−0.0048 (5)	−0.0016 (5)	−0.0027 (5)
C6	0.0123 (6)	0.0133 (6)	0.0142 (6)	−0.0033 (5)	−0.0003 (5)	−0.0029 (5)
C8	0.0223 (7)	0.0160 (6)	0.0144 (6)	−0.0098 (6)	−0.0030 (5)	−0.0002 (5)
C9	0.0180 (6)	0.0178 (7)	0.0141 (6)	−0.0087 (5)	−0.0062 (5)	0.0012 (5)
C10	0.0178 (7)	0.0164 (7)	0.0153 (6)	−0.0108 (5)	−0.0054 (5)	0.0004 (5)
C11	0.0153 (6)	0.0150 (6)	0.0182 (7)	−0.0068 (5)	−0.0049 (5)	−0.0004 (5)
C12	0.0206 (7)	0.0174 (7)	0.0146 (6)	−0.0084 (6)	−0.0058 (5)	0.0024 (5)
C13	0.0178 (7)	0.0190 (7)	0.0173 (7)	−0.0098 (6)	−0.0022 (5)	−0.0032 (5)
C14	0.0195 (7)	0.0131 (6)	0.0228 (7)	−0.0045 (5)	−0.0068 (6)	−0.0012 (5)
C15	0.0231 (7)	0.0163 (7)	0.0179 (7)	−0.0098 (6)	−0.0094 (6)	0.0031 (5)
C16	0.0278 (8)	0.0227 (7)	0.0181 (7)	0.0001 (6)	−0.0084 (6)	0.0033 (6)
C17	0.0223 (7)	0.0218 (7)	0.0265 (8)	−0.0052 (6)	0.0006 (6)	−0.0071 (6)
C18	0.0198 (7)	0.0155 (6)	0.0168 (7)	−0.0091 (5)	−0.0063 (5)	−0.0012 (5)
C19	0.0240 (7)	0.0232 (7)	0.0162 (7)	−0.0114 (6)	−0.0065 (6)	−0.0013 (5)
C20	0.0212 (8)	0.0354 (9)	0.0258 (8)	−0.0124 (7)	−0.0010 (6)	−0.0129 (6)

Cl1—C2	1.7537 (13)	C10—C11	1.4021 (18)
O1—C11	1.3703 (16)	C11—C12	1.3824 (19)
O1—C16	1.4213 (16)	C12—C13	1.3948 (19)
O2—C13	1.3700 (16)	C12—H12	0.9500
O2—C17	1.4270 (17)	C13—C14	1.3847 (19)
N1—C2	1.3256 (17)	C14—C15	1.3947 (19)
N1—C6	1.3574 (17)	C14—H14	0.9500
N3—C2	1.3130 (17)	C15—H15	0.9500
N3—C4	1.3496 (17)	C16—H16A	0.9800
N6—C6	1.3353 (17)	C16—H16B	0.9800
N6—C9	1.4532 (16)	C16—H16C	0.9800
N6—H6	0.8800	C17—H17A	0.9800
N7—C8	1.3201 (17)	C17—H17B	0.9800
N7—C5	1.3841 (17)	C17—H17C	0.9800
N9—C4	1.3655 (16)	C18—C19	1.5131 (18)
N9—C8	1.3676 (17)	C18—C20	1.5153 (19)
N9—C18	1.4831 (16)	C18—H18	1.0000
C4—C5	1.3866 (18)	C19—H19A	0.9800
C5—C6	1.4113 (18)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
C9—C10	1.5151 (18)	C20—H20A	0.9800
C9—H9A	0.9900	C20—H20B	0.9800
C9—H9B	0.9900	C20—H20C	0.9800
C10—C15	1.3799 (19)
C11—O1—C16	117.98 (10)	C13—C12—H12	120.2
C13—O2—C17	117.58 (11)	O2—C13—C14	125.13 (12)
C2—N1—C6	117.18 (11)	O2—C13—C12	114.52 (12)
C2—N3—C4	109.33 (11)	C14—C13—C12	120.35 (12)
C6—N6—C9	121.82 (11)	C13—C14—C15	118.82 (12)
C6—N6—H6	119.1	C13—C14—H14	120.6
C9—N6—H6	119.1	C15—C14—H14	120.6
C8—N7—C5	103.89 (11)	C10—C15—C14	122.29 (12)
C4—N9—C8	105.86 (10)	C10—C15—H15	118.9
C4—N9—C18	124.22 (11)	C14—C15—H15	118.9
C8—N9—C18	129.61 (11)	O1—C16—H16A	109.5
N3—C2—N1	132.07 (12)	O1—C16—H16B	109.5
N3—C2—Cl1	114.30 (10)	H16A—C16—H16B	109.5
N1—C2—Cl1	113.62 (9)	O1—C16—H16C	109.5
N3—C4—N9	126.58 (12)	H16A—C16—H16C	109.5
N3—C4—C5	127.06 (12)	H16B—C16—H16C	109.5
N9—C4—C5	106.35 (11)	O2—C17—H17A	109.5
N7—C5—C4	110.24 (11)	O2—C17—H17B	109.5
N7—C5—C6	133.27 (12)	H17A—C17—H17B	109.5
C4—C5—C6	116.46 (12)	O2—C17—H17C	109.5
N6—C6—N1	118.06 (11)	H17A—C17—H17C	109.5
N6—C6—C5	124.07 (12)	H17B—C17—H17C	109.5
N1—C6—C5	117.87 (11)	N9—C18—C19	111.14 (10)
N7—C8—N9	113.66 (12)	N9—C18—C20	108.83 (10)
N7—C8—H8	123.2	C19—C18—C20	113.22 (12)
N9—C8—H8	123.2	N9—C18—H18	107.8
N6—C9—C10	114.74 (11)	C19—C18—H18	107.8
N6—C9—H9A	108.6	C20—C18—H18	107.8
C10—C9—H9A	108.6	C18—C19—H19A	109.5
N6—C9—H9B	108.6	C18—C19—H19B	109.5
C10—C9—H9B	108.6	H19A—C19—H19B	109.5
H9A—C9—H9B	107.6	C18—C19—H19C	109.5
C15—C10—C11	117.63 (12)	H19A—C19—H19C	109.5
C15—C10—C9	123.29 (12)	H19B—C19—H19C	109.5
C11—C10—C9	119.04 (11)	C18—C20—H20A	109.5
O1—C11—C12	123.76 (11)	C18—C20—H20B	109.5
O1—C11—C10	114.88 (11)	H20A—C20—H20B	109.5
C12—C11—C10	121.36 (12)	C18—C20—H20C	109.5
C11—C12—C13	119.54 (12)	H20A—C20—H20C	109.5
C11—C12—H12	120.2	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7i	0.88	2.16	2.9465 (15)	148
C16—H16C···Cl1ii	0.98	2.78	3.4607 (15)	127
C19—H19A···O2iii	0.98	2.57	3.4709 (17)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7i	0.88	2.16	2.9465 (15)	148
C16—H16C⋯Cl1ii	0.98	2.78	3.4607 (15)	127
C19—H19A⋯O2iii	0.98	2.57	3.4709 (17)	154

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