2-Chloro-N-ethyl-9-isopropyl-9H-purin-6-amine.

In the title compound, C(10)H(14)ClN(5), the purine ring system is essentially planar, with an r.m.s. deviation from the least-squares plane defined by the nine constituent atoms of 0.0063 (11) Å. In the crystal, mol-ecules are linked by weak N-H⋯N and C-H⋯π inter-actions.

Related literature

For the synthesis, see: Fiorini & Abel (1998 ▶). For related structures, see: Kubicki & Codding (2001 ▶); Rouchal et al. (2009a ▶,b ▶, 2010 ▶). For other related literature, see: Legraverend & Grierson (2006 ▶).

Experimental

Crystal data

C10H14ClN5

M = 239.71

Monoclinic,

a = 8.1385 (2) Å

b = 9.6245 (2) Å

c = 14.8388 (3) Å

β = 92.997 (2)°

V = 1160.72 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 120 K

0.40 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector

Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009 ▶) T min = 0.973, T max = 1.000

13543 measured reflections

2041 independent reflections

1793 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.069

S = 1.07

2041 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.22 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 datablock(s) global, I. DOI: 10.1107/S1600536812035933/lx2254sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035933/lx2254Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035933/lx2254Isup3.cml

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

C10H14ClN5	F(000) = 504
Mr = 239.71	Dx = 1.372 Mg m−3
Monoclinic, P21/n	Melting point: 392 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.1385 (2) Å	Cell parameters from 9070 reflections
b = 9.6245 (2) Å	θ = 2.9–27.2°
c = 14.8388 (3) Å	µ = 0.31 mm−1
β = 92.997 (2)°	T = 120 K
V = 1160.72 (4) Å3	Block, colourless
Z = 4	0.40 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2041 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1793 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scan	h = −9→9
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	k = −10→11
Tmin = 0.973, Tmax = 1.000	l = −17→17
13543 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.3781P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.21 e Å−3
2041 reflections	Δρmin = −0.22 e Å−3
152 parameters

Experimental. Spectral properties of title compound:1H NMR (CDCl3): 1.30 (t, J = 7.3 Hz, 3H, NHCH2CH3), 1.57 (d, J = 6.6 Hz, 6H, CH(CH3)2), 3.72 (m, 2H, NHCH2CH3), 4.80 (septet, J = 6.9 Hz, 1H, CH(CH3)2), 5.84 (bs, 1H, NHCH2CH3), 7.76 (s, 1H, NC8HN) p.p.m.. 13 C NMR (CDCl3): 15.1(CH3), 23.0(CH3), 36.0(CH2), 47.1(CH), 119.0(C), 137.6(CH), 154.5(C), 155.5(C) p.p.m.. IR (KBr): 3103(m), 2974(m), 2933(w), 1726(w), 1605(s), 1560(m), 1481(w), 1454(w), 1435(w), 1404(m), 1362(m), 1309(s), 1227(s), 1188(w), 130(w), 1034(s), 941(m), 874(m), 785(m), 657(m), 609(w) cm-1. GC—EI—MS (200 °C, 70 eV): 241(M+(37Cl), 30), 240 (13), 239(M+(35Cl), 95), 226 (20), 225 (7), 224 (62), 213 (10), 211 (32), 199 (9), 198 (18), 197 (27), 196 (45), 184 (32), 183 (9), 182 (100), 171 (17), 169 (54), 161 (27), 160 (17), 156 (6), 155 (10), 154 (19), 153 (8), 146 (20), 134 (43), 133 (22), 120 (6), 119 (47), 118 (5), 108 (9), 107 (12), 106 (7), 93 (8), 92 (21), 80 (7), 68 (5), 67 (9), 66 (11), 65 (6), 55 (6), 54 (12), 53 (9), 44 (74), 43 (34), 42 (11), 41 (34), 40 (6) m/z(%). Elemental analysis calc for C10H14ClN4 (239.70) C 50.11, H 5.89, N 29.22; found C 50.16, H 5.92, N 29.02.

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	0.71286 (4)	0.25662 (4)	0.37828 (2)	0.02326 (12)
N1	0.46503 (13)	0.39081 (11)	0.30528 (7)	0.0176 (2)
N2	0.45822 (13)	0.33371 (11)	0.46370 (7)	0.0172 (2)
N3	0.24124 (14)	0.38987 (12)	0.55160 (7)	0.0195 (3)
H3	0.147 (2)	0.4230 (17)	0.5565 (11)	0.027 (4)*
N4	0.08494 (13)	0.52739 (11)	0.38017 (7)	0.0194 (3)
N5	0.21933 (13)	0.51796 (11)	0.25145 (7)	0.0180 (2)
C1	0.52134 (15)	0.33857 (13)	0.38306 (8)	0.0169 (3)
C2	0.31722 (15)	0.45181 (13)	0.31630 (8)	0.0164 (3)
C3	0.23370 (15)	0.45883 (13)	0.39493 (9)	0.0164 (3)
C4	0.30943 (15)	0.39438 (13)	0.47204 (8)	0.0166 (3)
C5	0.31812 (16)	0.31996 (15)	0.63006 (8)	0.0211 (3)
H5A	0.2794	0.3635	0.6855	0.025*
H5B	0.4388	0.3329	0.6301	0.025*
C6	0.27990 (19)	0.16560 (16)	0.63171 (10)	0.0312 (4)
H6A	0.3327	0.1238	0.6861	0.047*
H6B	0.3218	0.1212	0.5781	0.047*
H6C	0.1606	0.1521	0.6321	0.047*
C7	0.08323 (16)	0.56029 (14)	0.29428 (9)	0.0199 (3)
H7	−0.0051	0.6094	0.2644	0.024*
C8	0.25198 (17)	0.53989 (14)	0.15553 (9)	0.0210 (3)
H8	0.1594	0.5962	0.1277	0.025*
C9	0.40995 (17)	0.62252 (15)	0.14745 (9)	0.0250 (3)
H9A	0.4035	0.7089	0.1820	0.038*
H9B	0.4244	0.6445	0.0839	0.038*
H9C	0.5037	0.5674	0.1712	0.038*
C10	0.25535 (19)	0.40217 (16)	0.10584 (10)	0.0285 (3)
H10A	0.1506	0.3537	0.1119	0.043*
H10B	0.3455	0.3448	0.1317	0.043*
H10C	0.2722	0.4190	0.0418	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.01873 (19)	0.0305 (2)	0.02086 (19)	0.00947 (13)	0.00355 (13)	0.00232 (13)
N1	0.0166 (6)	0.0174 (6)	0.0189 (6)	0.0010 (4)	0.0019 (4)	−0.0002 (4)
N2	0.0164 (5)	0.0172 (6)	0.0181 (5)	0.0006 (4)	0.0015 (4)	−0.0013 (4)
N3	0.0169 (6)	0.0237 (6)	0.0181 (6)	0.0048 (5)	0.0037 (4)	0.0010 (4)
N4	0.0170 (6)	0.0193 (6)	0.0220 (6)	0.0021 (4)	0.0018 (4)	0.0002 (5)
N5	0.0164 (6)	0.0199 (6)	0.0179 (5)	0.0021 (4)	0.0012 (4)	0.0019 (5)
C1	0.0148 (6)	0.0156 (7)	0.0203 (6)	0.0007 (5)	0.0019 (5)	−0.0015 (5)
C2	0.0158 (6)	0.0141 (7)	0.0191 (6)	−0.0012 (5)	−0.0004 (5)	−0.0003 (5)
C3	0.0151 (6)	0.0143 (7)	0.0200 (6)	−0.0007 (5)	0.0014 (5)	−0.0015 (5)
C4	0.0169 (6)	0.0136 (6)	0.0192 (6)	−0.0023 (5)	0.0010 (5)	−0.0027 (5)
C5	0.0202 (7)	0.0265 (8)	0.0166 (6)	0.0029 (6)	0.0020 (5)	0.0003 (5)
C6	0.0311 (8)	0.0295 (9)	0.0329 (8)	−0.0026 (6)	0.0016 (6)	0.0085 (6)
C7	0.0159 (6)	0.0200 (7)	0.0238 (7)	0.0025 (5)	0.0014 (5)	0.0015 (6)
C8	0.0202 (7)	0.0261 (8)	0.0169 (6)	0.0038 (5)	0.0008 (5)	0.0044 (5)
C9	0.0255 (7)	0.0241 (8)	0.0258 (7)	0.0015 (6)	0.0046 (6)	0.0065 (6)
C10	0.0300 (8)	0.0333 (9)	0.0220 (7)	−0.0012 (6)	−0.0001 (6)	−0.0046 (6)

Cl1—C1	1.7516 (13)	C5—H5A	0.9900
N1—C1	1.3189 (16)	C5—H5B	0.9900
N1—C2	1.3561 (16)	C6—H6A	0.9800
N2—C1	1.3274 (16)	C6—H6B	0.9800
N2—C4	1.3558 (16)	C6—H6C	0.9800
N3—C4	1.3312 (17)	C7—H7	0.9500
N3—C5	1.4572 (17)	C8—C10	1.518 (2)
N3—H3	0.837 (17)	C8—C9	1.5217 (19)
N4—C7	1.3126 (17)	C8—H8	1.0000
N4—C3	1.3861 (17)	C9—H9A	0.9800
N5—C7	1.3677 (17)	C9—H9B	0.9800
N5—C2	1.3733 (16)	C9—H9C	0.9800
N5—C8	1.4766 (16)	C10—H10A	0.9800
C2—C3	1.3824 (18)	C10—H10B	0.9800
C3—C4	1.4143 (18)	C10—H10C	0.9800
C5—C6	1.518 (2)
C1—N1—C2	109.23 (11)	C5—C6—H6A	109.5
C1—N2—C4	117.17 (11)	C5—C6—H6B	109.5
C4—N3—C5	122.83 (12)	H6A—C6—H6B	109.5
C4—N3—H3	119.4 (11)	C5—C6—H6C	109.5
C5—N3—H3	117.6 (11)	H6A—C6—H6C	109.5
C7—N4—C3	103.48 (10)	H6B—C6—H6C	109.5
C7—N5—C2	105.47 (10)	N4—C7—N5	114.31 (12)
C7—N5—C8	126.60 (11)	N4—C7—H7	122.8
C2—N5—C8	127.93 (11)	N5—C7—H7	122.8
N1—C1—N2	132.00 (12)	N5—C8—C10	110.62 (11)
N1—C1—Cl1	113.92 (9)	N5—C8—C9	110.24 (11)
N2—C1—Cl1	114.06 (9)	C10—C8—C9	112.42 (12)
N1—C2—N5	127.02 (11)	N5—C8—H8	107.8
N1—C2—C3	126.96 (12)	C10—C8—H8	107.8
N5—C2—C3	106.02 (11)	C9—C8—H8	107.8
C2—C3—N4	110.72 (11)	C8—C9—H9A	109.5
C2—C3—C4	116.66 (12)	C8—C9—H9B	109.5
N4—C3—C4	132.59 (12)	H9A—C9—H9B	109.5
N3—C4—N2	118.86 (12)	C8—C9—H9C	109.5
N3—C4—C3	123.20 (12)	H9A—C9—H9C	109.5
N2—C4—C3	117.94 (11)	H9B—C9—H9C	109.5
N3—C5—C6	112.64 (11)	C8—C10—H10A	109.5
N3—C5—H5A	109.1	C8—C10—H10B	109.5
C6—C5—H5A	109.1	H10A—C10—H10B	109.5
N3—C5—H5B	109.1	C8—C10—H10C	109.5
C6—C5—H5B	109.1	H10A—C10—H10C	109.5
H5A—C5—H5B	107.8	H10B—C10—H10C	109.5
C2—N1—C1—N2	2.0 (2)	C5—N3—C4—N2	−1.24 (19)
C2—N1—C1—Cl1	−179.87 (9)	C5—N3—C4—C3	178.29 (12)
C4—N2—C1—N1	−1.4 (2)	C1—N2—C4—N3	179.07 (11)
C4—N2—C1—Cl1	−179.56 (9)	C1—N2—C4—C3	−0.48 (17)
C1—N1—C2—N5	179.90 (12)	C2—C3—C4—N3	−178.20 (12)
C1—N1—C2—C3	−0.80 (18)	N4—C3—C4—N3	−0.3 (2)
C7—N5—C2—N1	179.21 (12)	C2—C3—C4—N2	1.33 (17)
C8—N5—C2—N1	−0.8 (2)	N4—C3—C4—N2	179.24 (13)
C7—N5—C2—C3	−0.21 (14)	C4—N3—C5—C6	−85.04 (16)
C8—N5—C2—C3	179.74 (12)	C3—N4—C7—N5	0.27 (15)
N1—C2—C3—N4	−179.04 (12)	C2—N5—C7—N4	−0.05 (15)
N5—C2—C3—N4	0.38 (14)	C8—N5—C7—N4	−179.99 (12)
N1—C2—C3—C4	−0.68 (19)	C7—N5—C8—C10	−114.50 (14)
N5—C2—C3—C4	178.74 (11)	C2—N5—C8—C10	65.56 (16)
C7—N4—C3—C2	−0.40 (14)	C7—N5—C8—C9	120.53 (14)
C7—N4—C3—C4	−178.41 (14)	C2—N5—C8—C9	−59.40 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N4i	0.837 (16)	2.205 (17)	2.9979 (16)	158.2 (15)
C8—H8···Cg1ii	1.00 (1)	2.90 (1)	3.6403 (13)	131 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the center of gravity of the pyridine ring (C1/N1/C2–C4/ N2).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N4i	0.837 (16)	2.205 (17)	2.9979 (16)	158.2 (15)
C8—H8⋯Cg1ii	1.00 (1)	2.90 (1)	3.6403 (13)	131 (1)

Symmetry codes: (i) ; (ii) .