N-(2-Meth-oxy-benz-yl)-9-(oxolan-2-yl)-9H-purin-6-amine.

The title compound, C17H19N5O2, features an almost planar purine skeleton (r.m.s. deviation = 0.009 Å) substituted by a tetra-hydro-furan ring, which adopts an envelope conformation. The purine and benzene rings subtend a dihedral angle of 66.70 (3)°. In the crystal, pairs of N-H⋯N hydrogen bonds connect adjacent mol-ecules into inversion dimers. C-H⋯N, C-H⋯O, C-H⋯π and π-π inter-actions [pyrimidine ring centroid-centroid distance = 3.3909 (1) Å] connect the dimers into a three-dimensional architecture.

Related literature

For an alternative synthetic procedure and the biological activity of benzyl-substituted 6-benzyl­amino-9-tetra­hydro­pyran-2-yl-9H-purine derivatives, see: Szüčová et al. (2009 ▶). For a related structure, see: Štarha et al. (2013 ▶).

Experimental

Crystal data

C17H19N5O2

M = 325.37

Monoclinic,

a = 8.87210 (19) Å

b = 8.37534 (17) Å

c = 20.7445 (4) Å

β = 90.4360 (19)°

V = 1541.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 110 K

0.35 × 0.30 × 0.30 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.967, T max = 0.972

12687 measured reflections

2719 independent reflections

2415 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.04

2719 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.23 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: 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/S1600536813007721/ng5319sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007721/ng5319Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007721/ng5319Isup3.cml

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

C17H19N5O2	F(000) = 688
Mr = 325.37	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11022 reflections
a = 8.87210 (19) Å	θ = 2.9–31.9°
b = 8.37534 (17) Å	µ = 0.10 mm−1
c = 20.7445 (4) Å	T = 110 K
β = 90.4360 (19)°	Prism, colourless
V = 1541.42 (6) Å3	0.35 × 0.30 × 0.30 mm
Z = 4

Agilent Xcalibur Sapphire2 diffractometer	2719 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.3611 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→9
Tmin = 0.967, Tmax = 0.972	l = −23→24
12687 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.7716P] where P = (Fo2 + 2Fc2)/3
2719 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.23 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
N1	0.08392 (13)	0.72477 (14)	0.53161 (5)	0.0216 (3)
O1	0.39104 (11)	1.15624 (12)	0.40650 (5)	0.0265 (2)
O2	0.14507 (12)	0.19144 (12)	0.72047 (5)	0.0295 (3)
C2	−0.02259 (15)	0.65607 (17)	0.56768 (6)	0.0214 (3)
H2	−0.1142	0.7142	0.5709	0.026*
N3	−0.01895 (12)	0.51849 (14)	0.59968 (5)	0.0208 (3)
C4	0.11411 (15)	0.44422 (16)	0.59082 (6)	0.0184 (3)
C5	0.23360 (15)	0.49756 (16)	0.55428 (6)	0.0188 (3)
N6	0.32579 (13)	0.71553 (14)	0.48978 (6)	0.0241 (3)
H6	0.4078	0.6597	0.4822	0.029*
C6	0.21608 (15)	0.64750 (16)	0.52444 (6)	0.0190 (3)
N7	0.35162 (13)	0.38842 (14)	0.55594 (6)	0.0241 (3)
C8	0.30091 (16)	0.27427 (18)	0.59319 (7)	0.0257 (3)
H8	0.3582	0.1818	0.6036	0.031*
N9	0.15811 (12)	0.29976 (14)	0.61589 (6)	0.0216 (3)
C9	0.31619 (17)	0.87629 (17)	0.46427 (7)	0.0247 (3)
H9A	0.3913	0.9444	0.4867	0.030*
H9B	0.2149	0.9201	0.4733	0.030*
C10	0.34376 (14)	0.88340 (16)	0.39253 (7)	0.0197 (3)
C11	0.38461 (14)	1.02956 (17)	0.36481 (7)	0.0203 (3)
C12	0.41548 (16)	1.03960 (19)	0.29956 (7)	0.0257 (3)
H12	0.4460	1.1383	0.2812	0.031*
C13	0.40157 (16)	0.90491 (19)	0.26119 (7)	0.0291 (4)
H13	0.4219	0.9119	0.2164	0.035*
C14	0.35861 (16)	0.76098 (19)	0.28742 (7)	0.0270 (3)
H14	0.3484	0.6692	0.2608	0.032*
C15	0.33028 (15)	0.75093 (17)	0.35321 (7)	0.0228 (3)
H15	0.3013	0.6515	0.3713	0.027*
C16	0.42614 (18)	1.30910 (18)	0.38005 (8)	0.0307 (4)
H16A	0.4216	1.3901	0.4141	0.046*
H16B	0.3531	1.3354	0.3460	0.046*
H16C	0.5278	1.3067	0.3619	0.046*
C17	0.06967 (16)	0.20020 (17)	0.66006 (7)	0.0242 (3)
H17	−0.0313	0.2506	0.6663	0.029*
C18	0.04761 (17)	0.02969 (18)	0.63684 (7)	0.0278 (3)
H18A	0.0622	0.0218	0.5897	0.033*
H18B	−0.0544	−0.0098	0.6475	0.033*
C19	0.16852 (17)	−0.06373 (18)	0.67324 (7)	0.0275 (3)
H19A	0.1373	−0.1757	0.6805	0.033*
H19B	0.2656	−0.0625	0.6500	0.033*
C20	0.17883 (17)	0.02796 (18)	0.73579 (7)	0.0292 (4)
H20A	0.1055	−0.0142	0.7672	0.035*
H20B	0.2814	0.0190	0.7546	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0222 (6)	0.0213 (6)	0.0211 (6)	0.0008 (5)	0.0011 (5)	0.0005 (5)
O1	0.0342 (6)	0.0177 (5)	0.0276 (5)	−0.0020 (4)	0.0020 (4)	0.0026 (4)
O2	0.0407 (6)	0.0234 (6)	0.0245 (5)	0.0000 (5)	0.0005 (5)	0.0013 (4)
C2	0.0208 (7)	0.0209 (7)	0.0224 (7)	0.0018 (6)	0.0021 (5)	−0.0016 (6)
N3	0.0202 (6)	0.0216 (6)	0.0207 (6)	0.0003 (5)	0.0022 (5)	−0.0009 (5)
C4	0.0198 (7)	0.0182 (7)	0.0171 (6)	−0.0017 (5)	−0.0017 (5)	−0.0016 (5)
C5	0.0191 (7)	0.0202 (7)	0.0170 (7)	−0.0011 (5)	0.0000 (5)	−0.0010 (5)
N6	0.0225 (6)	0.0234 (6)	0.0265 (6)	0.0029 (5)	0.0064 (5)	0.0077 (5)
C6	0.0220 (7)	0.0208 (7)	0.0142 (6)	−0.0023 (6)	−0.0002 (5)	−0.0015 (5)
N7	0.0204 (6)	0.0221 (6)	0.0298 (7)	0.0009 (5)	0.0041 (5)	0.0043 (5)
C8	0.0191 (7)	0.0223 (8)	0.0360 (8)	0.0020 (6)	0.0042 (6)	0.0061 (6)
N9	0.0181 (6)	0.0202 (6)	0.0266 (6)	−0.0002 (5)	0.0023 (5)	0.0046 (5)
C9	0.0286 (8)	0.0219 (8)	0.0237 (7)	−0.0017 (6)	0.0036 (6)	0.0044 (6)
C10	0.0137 (6)	0.0223 (7)	0.0232 (7)	0.0020 (5)	0.0012 (5)	0.0039 (6)
C11	0.0153 (6)	0.0210 (7)	0.0246 (7)	0.0004 (5)	−0.0011 (5)	0.0018 (6)
C12	0.0228 (7)	0.0290 (8)	0.0254 (7)	−0.0026 (6)	0.0003 (6)	0.0092 (6)
C13	0.0263 (8)	0.0407 (9)	0.0202 (7)	−0.0004 (7)	0.0012 (6)	0.0022 (7)
C14	0.0234 (7)	0.0309 (8)	0.0267 (8)	0.0001 (6)	−0.0017 (6)	−0.0049 (6)
C15	0.0166 (7)	0.0213 (7)	0.0303 (8)	0.0003 (5)	−0.0008 (6)	0.0033 (6)
C16	0.0365 (9)	0.0194 (8)	0.0363 (9)	−0.0038 (6)	−0.0038 (7)	0.0071 (6)
C17	0.0186 (7)	0.0244 (8)	0.0296 (8)	−0.0002 (6)	0.0026 (6)	0.0041 (6)
C18	0.0262 (8)	0.0239 (8)	0.0334 (8)	−0.0044 (6)	−0.0024 (6)	0.0023 (7)
C19	0.0269 (8)	0.0207 (8)	0.0350 (8)	0.0009 (6)	0.0006 (6)	0.0015 (6)
C20	0.0298 (8)	0.0242 (8)	0.0334 (8)	0.0004 (6)	−0.0019 (6)	0.0043 (7)

N1—C2	1.3396 (18)	C10—C15	1.382 (2)
N1—C6	1.3485 (18)	C10—C11	1.4014 (19)
O1—C11	1.3698 (17)	C11—C12	1.385 (2)
O1—C16	1.4282 (17)	C12—C13	1.386 (2)
O2—C17	1.4179 (18)	C12—H12	0.9500
O2—C20	1.4366 (18)	C13—C14	1.377 (2)
C2—N3	1.3302 (18)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.392 (2)
N3—C4	1.3482 (17)	C14—H14	0.9500
C4—N9	1.3725 (18)	C15—H15	0.9500
C4—C5	1.3821 (19)	C16—H16A	0.9800
C5—N7	1.3902 (17)	C16—H16B	0.9800
C5—C6	1.4082 (19)	C16—H16C	0.9800
N6—C6	1.3414 (17)	C17—C18	1.519 (2)
N6—C9	1.4490 (18)	C17—H17	1.0000
N6—H6	0.8800	C18—C19	1.523 (2)
N7—C8	1.3111 (19)	C18—H18A	0.9900
C8—N9	1.3716 (18)	C18—H18B	0.9900
C8—H8	0.9500	C19—C20	1.510 (2)
N9—C17	1.4701 (18)	C19—H19A	0.9900
C9—C10	1.5111 (19)	C19—H19B	0.9900
C9—H9A	0.9900	C20—H20A	0.9900
C9—H9B	0.9900	C20—H20B	0.9900
C2—N1—C6	118.24 (12)	C11—C12—H12	120.2
C11—O1—C16	117.38 (11)	C14—C13—C12	120.62 (13)
C17—O2—C20	109.94 (11)	C14—C13—H13	119.7
N3—C2—N1	129.52 (13)	C12—C13—H13	119.7
N3—C2—H2	115.2	C13—C14—C15	119.51 (14)
N1—C2—H2	115.2	C13—C14—H14	120.2
C2—N3—C4	110.46 (11)	C15—C14—H14	120.2
N3—C4—N9	127.00 (12)	C10—C15—C14	120.98 (13)
N3—C4—C5	126.99 (13)	C10—C15—H15	119.5
N9—C4—C5	106.00 (12)	C14—C15—H15	119.5
C4—C5—N7	110.77 (12)	O1—C16—H16A	109.5
C4—C5—C6	116.54 (12)	O1—C16—H16B	109.5
N7—C5—C6	132.67 (12)	H16A—C16—H16B	109.5
C6—N6—C9	123.33 (12)	O1—C16—H16C	109.5
C6—N6—H6	118.3	H16A—C16—H16C	109.5
C9—N6—H6	118.3	H16B—C16—H16C	109.5
N6—C6—N1	119.37 (12)	O2—C17—N9	109.25 (11)
N6—C6—C5	122.43 (12)	O2—C17—C18	106.88 (11)
N1—C6—C5	118.20 (12)	N9—C17—C18	113.81 (12)
C8—N7—C5	103.43 (11)	O2—C17—H17	108.9
N7—C8—N9	114.26 (13)	N9—C17—H17	108.9
N7—C8—H8	122.9	C18—C17—H17	108.9
N9—C8—H8	122.9	C17—C18—C19	103.72 (12)
C8—N9—C4	105.54 (11)	C17—C18—H18A	111.0
C8—N9—C17	128.64 (12)	C19—C18—H18A	111.0
C4—N9—C17	125.77 (11)	C17—C18—H18B	111.0
N6—C9—C10	112.76 (12)	C19—C18—H18B	111.0
N6—C9—H9A	109.0	H18A—C18—H18B	109.0
C10—C9—H9A	109.0	C20—C19—C18	101.68 (12)
N6—C9—H9B	109.0	C20—C19—H19A	111.4
C10—C9—H9B	109.0	C18—C19—H19A	111.4
H9A—C9—H9B	107.8	C20—C19—H19B	111.4
C15—C10—C11	118.73 (12)	C18—C19—H19B	111.4
C15—C10—C9	122.39 (12)	H19A—C19—H19B	109.3
C11—C10—C9	118.88 (12)	O2—C20—C19	106.47 (12)
O1—C11—C12	124.21 (13)	O2—C20—H20A	110.4
O1—C11—C10	115.28 (12)	C19—C20—H20A	110.4
C12—C11—C10	120.51 (13)	O2—C20—H20B	110.4
C13—C12—C11	119.63 (13)	C19—C20—H20B	110.4
C13—C12—H12	120.2	H20A—C20—H20B	108.6

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7i	0.88	2.32	3.145 (2)	157
C8—H8···Cgi	0.95	2.86	3.6214 (14)	138
C12—H12···O2ii	0.95	2.60	3.459 (2)	150
C13—H13···N3ii	0.95	2.55	3.489 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7i	0.88	2.32	3.145 (2)	157
C8—H8⋯Cg i	0.95	2.86	3.6214 (14)	138
C12—H12⋯O2ii	0.95	2.60	3.459 (2)	150
C13—H13⋯N3ii	0.95	2.55	3.489 (2)	170

Symmetry codes: (i) ; (ii) .