6-(3,5-Dimeth-oxy-benzyl-amino)-9-(oxan-2-yl)-9H-purine.

The mol-ecule of the title compound, C19H23N5O3, contains six-membered pyrimidine and five-membered imidazole rings merged into the essentially planar purine skeleton (r.m.s. deviation = 0.01 Å). In the crystal, pairs of N-H⋯N hydrogen bonds link mol-ecules into inversion dimers. The dimers are linked via C-H⋯O hydrogen bonds, forming double-stranded chains propagating along [001]. These chains are linked via C-H⋯π and parallel slipped π-π inter-actions [centroid-centroid distance = 3.467 (1) Å; slippage 0.519 Å], forming a three-dimensional network.

Related literature

For the alternative synthetic procedure and biological activity of the title compound, see: Szüčová et al. (2009 ▶). For the structures of similar compounds, see: Soriano-Garcia et al. (2003 ▶); Taddei et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H23N5O3

M = 369.42

Triclinic,

a = 8.6978 (3) Å

b = 8.8318 (3) Å

c = 12.1517 (4) Å

α = 84.808 (3)°

β = 78.674 (3)°

γ = 82.039 (3)°

V = 904.53 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 110 K

0.40 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶). T min = 0.963, T max = 0.968

6684 measured reflections

3177 independent reflections

2784 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.07

3177 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.22 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/S1600536813006697/zq2196sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006697/zq2196Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006697/zq2196Isup3.cml

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

C19H23N5O3	Z = 2
Mr = 369.42	F(000) = 392
Triclinic, P1	Dx = 1.356 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6978 (3) Å	Cell parameters from 6498 reflections
b = 8.8318 (3) Å	θ = 3.0–31.7°
c = 12.1517 (4) Å	µ = 0.10 mm−1
α = 84.808 (3)°	T = 110 K
β = 78.674 (3)°	Prism, colourless
γ = 82.039 (3)°	0.40 × 0.40 × 0.35 mm
V = 904.53 (5) Å3

Agilent Xcalibur Sapphire2 diffractometer	3177 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
Detector resolution: 8.3611 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012).	k = −10→9
Tmin = 0.963, Tmax = 0.968	l = −14→14
6684 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.5406P] where P = (Fo2 + 2Fc2)/3
3177 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.22 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
O1	0.34333 (13)	0.54945 (15)	0.18751 (10)	0.0325 (3)
N1	0.74662 (17)	0.93176 (17)	0.56497 (14)	0.0343 (4)
O2	0.86794 (14)	0.66871 (15)	0.06254 (11)	0.0348 (3)
C2	0.7939 (2)	1.0254 (2)	0.62854 (19)	0.0393 (5)
H2	0.7252	1.1178	0.6431	0.047*
N3	0.92245 (18)	1.00924 (17)	0.67466 (14)	0.0347 (4)
O3	1.14994 (17)	0.82537 (18)	0.87030 (12)	0.0457 (4)
C4	1.01114 (19)	0.87587 (19)	0.64793 (14)	0.0253 (4)
C5	0.98030 (19)	0.76782 (18)	0.58273 (14)	0.0240 (4)
N6	0.79042 (16)	0.70162 (17)	0.47898 (12)	0.0289 (3)
H6	0.8574	0.6235	0.4525	0.035*
C6	0.83853 (19)	0.79912 (19)	0.54048 (14)	0.0260 (4)
N7	1.09793 (16)	0.64320 (16)	0.57585 (12)	0.0269 (3)
C8	1.19489 (19)	0.67977 (19)	0.63655 (15)	0.0265 (4)
H8	1.2878	0.6148	0.6480	0.032*
N9	1.15153 (16)	0.81862 (15)	0.68192 (12)	0.0250 (3)
C9	0.6313 (2)	0.7216 (2)	0.45512 (15)	0.0302 (4)
H9A	0.5858	0.8299	0.4635	0.036*
H9B	0.5652	0.6577	0.5113	0.036*
C10	0.62444 (19)	0.67918 (18)	0.33892 (14)	0.0245 (4)
C11	0.48482 (19)	0.63085 (18)	0.32182 (14)	0.0244 (4)
H11	0.3985	0.6226	0.3826	0.029*
C12	0.47421 (19)	0.59515 (18)	0.21484 (15)	0.0251 (4)
C13	0.6021 (2)	0.60276 (19)	0.12598 (15)	0.0270 (4)
H13	0.5954	0.5746	0.0536	0.032*
C14	0.73869 (19)	0.65179 (19)	0.14429 (15)	0.0262 (4)
C15	0.75085 (19)	0.69009 (18)	0.25110 (14)	0.0255 (4)
H15	0.8452	0.7233	0.2632	0.031*
C16	0.2009 (2)	0.5642 (2)	0.26940 (16)	0.0374 (5)
H16A	0.1155	0.5309	0.2391	0.056*
H16B	0.1729	0.6716	0.2877	0.056*
H16C	0.2164	0.5004	0.3375	0.056*
C17	0.8598 (2)	0.6274 (3)	−0.04723 (16)	0.0421 (5)
H17A	0.9599	0.6404	−0.0984	0.063*
H17B	0.7734	0.6933	−0.0751	0.063*
H17C	0.8403	0.5202	−0.0433	0.063*
C18	1.2218 (2)	0.88515 (19)	0.76217 (15)	0.0278 (4)
H18	1.1926	0.9988	0.7569	0.033*
C19	1.2010 (3)	0.8915 (3)	0.95875 (19)	0.0599 (7)
H19A	1.1479	0.8498	1.0327	0.072*
H19B	1.1712	1.0039	0.9541	0.072*
C20	1.3771 (3)	0.8561 (3)	0.9489 (2)	0.0600 (7)
H20A	1.4064	0.7439	0.9578	0.072*
H20B	1.4112	0.9037	1.0093	0.072*
C21	1.4591 (3)	0.9167 (3)	0.8360 (2)	0.0486 (6)
H21A	1.5746	0.8868	0.8279	0.058*
H21B	1.4389	1.0300	0.8302	0.058*
C22	1.3974 (2)	0.8509 (2)	0.74142 (18)	0.0381 (5)
H22A	1.4431	0.8983	0.6674	0.046*
H22B	1.4289	0.7388	0.7412	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (6)	0.0443 (8)	0.0359 (7)	−0.0083 (5)	−0.0071 (5)	−0.0122 (6)
N1	0.0259 (8)	0.0266 (8)	0.0536 (10)	0.0034 (6)	−0.0173 (7)	−0.0084 (7)
O2	0.0270 (7)	0.0448 (8)	0.0353 (7)	−0.0124 (6)	−0.0040 (5)	−0.0088 (6)
C2	0.0283 (10)	0.0256 (9)	0.0678 (14)	0.0061 (7)	−0.0193 (9)	−0.0143 (9)
N3	0.0269 (8)	0.0245 (8)	0.0561 (10)	0.0023 (6)	−0.0157 (7)	−0.0123 (7)
O3	0.0487 (9)	0.0562 (9)	0.0373 (8)	−0.0194 (7)	−0.0102 (6)	−0.0057 (7)
C4	0.0207 (8)	0.0224 (8)	0.0341 (9)	−0.0019 (6)	−0.0082 (7)	−0.0033 (7)
C5	0.0209 (8)	0.0224 (8)	0.0295 (9)	−0.0012 (6)	−0.0070 (7)	−0.0029 (7)
N6	0.0231 (7)	0.0306 (8)	0.0360 (8)	0.0043 (6)	−0.0145 (6)	−0.0101 (6)
C6	0.0225 (8)	0.0257 (9)	0.0310 (9)	−0.0008 (7)	−0.0084 (7)	−0.0031 (7)
N7	0.0221 (7)	0.0256 (7)	0.0347 (8)	0.0019 (6)	−0.0109 (6)	−0.0068 (6)
C8	0.0227 (8)	0.0219 (8)	0.0367 (9)	0.0018 (6)	−0.0115 (7)	−0.0054 (7)
N9	0.0221 (7)	0.0213 (7)	0.0344 (8)	−0.0014 (5)	−0.0118 (6)	−0.0046 (6)
C9	0.0217 (8)	0.0357 (10)	0.0352 (10)	0.0016 (7)	−0.0116 (7)	−0.0069 (8)
C10	0.0233 (8)	0.0177 (8)	0.0340 (9)	0.0040 (6)	−0.0132 (7)	−0.0034 (7)
C11	0.0214 (8)	0.0205 (8)	0.0316 (9)	0.0022 (6)	−0.0078 (7)	−0.0039 (7)
C12	0.0215 (8)	0.0202 (8)	0.0363 (9)	−0.0013 (6)	−0.0119 (7)	−0.0044 (7)
C13	0.0264 (9)	0.0259 (9)	0.0312 (9)	−0.0017 (7)	−0.0104 (7)	−0.0059 (7)
C14	0.0224 (8)	0.0223 (8)	0.0341 (9)	−0.0014 (6)	−0.0064 (7)	−0.0026 (7)
C15	0.0214 (8)	0.0200 (8)	0.0378 (10)	−0.0006 (6)	−0.0131 (7)	−0.0027 (7)
C16	0.0238 (9)	0.0543 (12)	0.0373 (10)	−0.0112 (8)	−0.0048 (8)	−0.0116 (9)
C17	0.0347 (10)	0.0602 (13)	0.0348 (10)	−0.0167 (9)	−0.0037 (8)	−0.0096 (9)
C18	0.0311 (9)	0.0207 (8)	0.0360 (10)	−0.0055 (7)	−0.0144 (8)	−0.0031 (7)
C19	0.0812 (18)	0.0688 (16)	0.0379 (12)	−0.0238 (14)	−0.0180 (12)	−0.0101 (11)
C20	0.0923 (19)	0.0450 (13)	0.0620 (15)	−0.0279 (13)	−0.0523 (14)	0.0076 (11)
C21	0.0400 (12)	0.0424 (12)	0.0728 (16)	−0.0082 (9)	−0.0319 (11)	−0.0014 (11)
C22	0.0238 (9)	0.0453 (11)	0.0477 (12)	−0.0038 (8)	−0.0140 (8)	−0.0015 (9)

O1—C12	1.3672 (19)	C11—C12	1.388 (2)
O1—C16	1.427 (2)	C11—H11	0.9500
N1—C2	1.336 (2)	C12—C13	1.394 (2)
N1—C6	1.345 (2)	C13—C14	1.383 (2)
O2—C14	1.362 (2)	C13—H13	0.9500
O2—C17	1.432 (2)	C14—C15	1.398 (2)
C2—N3	1.331 (2)	C15—H15	0.9500
C2—H2	0.9500	C16—H16A	0.9800
N3—C4	1.344 (2)	C16—H16B	0.9800
O3—C18	1.428 (2)	C16—H16C	0.9800
O3—C19	1.438 (2)	C17—H17A	0.9800
C4—C5	1.379 (2)	C17—H17B	0.9800
C4—N9	1.381 (2)	C17—H17C	0.9800
C5—N7	1.392 (2)	C18—C22	1.491 (2)
C5—C6	1.410 (2)	C18—H18	1.0000
N6—C6	1.347 (2)	C19—C20	1.503 (4)
N6—C9	1.453 (2)	C19—H19A	0.9900
N6—H6	0.8800	C19—H19B	0.9900
N7—C8	1.312 (2)	C20—C21	1.504 (3)
C8—N9	1.365 (2)	C20—H20A	0.9900
C8—H8	0.9500	C20—H20B	0.9900
N9—C18	1.451 (2)	C21—C22	1.548 (3)
C9—C10	1.508 (2)	C21—H21A	0.9900
C9—H9A	0.9900	C21—H21B	0.9900
C9—H9B	0.9900	C22—H22A	0.9900
C10—C15	1.381 (2)	C22—H22B	0.9900
C10—C11	1.400 (2)
C12—O1—C16	117.27 (13)	C13—C14—C15	120.74 (16)
C2—N1—C6	118.32 (15)	C10—C15—C14	119.37 (15)
C14—O2—C17	116.38 (13)	C10—C15—H15	120.3
N3—C2—N1	129.90 (16)	C14—C15—H15	120.3
N3—C2—H2	115.0	O1—C16—H16A	109.5
N1—C2—H2	115.0	O1—C16—H16B	109.5
C2—N3—C4	109.91 (15)	H16A—C16—H16B	109.5
C18—O3—C19	111.26 (15)	O1—C16—H16C	109.5
N3—C4—C5	127.40 (15)	H16A—C16—H16C	109.5
N3—C4—N9	126.56 (15)	H16B—C16—H16C	109.5
C5—C4—N9	106.04 (14)	O2—C17—H17A	109.5
C4—C5—N7	110.73 (14)	O2—C17—H17B	109.5
C4—C5—C6	116.57 (15)	H17A—C17—H17B	109.5
N7—C5—C6	132.65 (15)	O2—C17—H17C	109.5
C6—N6—C9	121.98 (14)	H17A—C17—H17C	109.5
C6—N6—H6	119.0	H17B—C17—H17C	109.5
C9—N6—H6	119.0	O3—C18—N9	105.55 (13)
N1—C6—N6	119.01 (15)	O3—C18—C22	112.37 (15)
N1—C6—C5	117.88 (15)	N9—C18—C22	112.58 (15)
N6—C6—C5	123.10 (15)	O3—C18—H18	108.7
C8—N7—C5	103.34 (14)	N9—C18—H18	108.7
N7—C8—N9	114.60 (14)	C22—C18—H18	108.7
N7—C8—H8	122.7	O3—C19—C20	110.3 (2)
N9—C8—H8	122.7	O3—C19—H19A	109.6
C8—N9—C4	105.29 (13)	C20—C19—H19A	109.6
C8—N9—C18	128.47 (14)	O3—C19—H19B	109.6
C4—N9—C18	125.68 (14)	C20—C19—H19B	109.6
N6—C9—C10	113.44 (14)	H19A—C19—H19B	108.1
N6—C9—H9A	108.9	C19—C20—C21	110.10 (18)
C10—C9—H9A	108.9	C19—C20—H20A	109.6
N6—C9—H9B	108.9	C21—C20—H20A	109.6
C10—C9—H9B	108.9	C19—C20—H20B	109.6
H9A—C9—H9B	107.7	C21—C20—H20B	109.6
C15—C10—C11	120.70 (15)	H20A—C20—H20B	108.2
C15—C10—C9	121.21 (15)	C20—C21—C22	109.71 (17)
C11—C10—C9	118.08 (15)	C20—C21—H21A	109.7
C12—C11—C10	119.11 (16)	C22—C21—H21A	109.7
C12—C11—H11	120.4	C20—C21—H21B	109.7
C10—C11—H11	120.4	C22—C21—H21B	109.7
O1—C12—C11	124.41 (15)	H21A—C21—H21B	108.2
O1—C12—C13	114.85 (15)	C18—C22—C21	108.40 (16)
C11—C12—C13	120.74 (15)	C18—C22—H22A	110.0
C14—C13—C12	119.31 (16)	C21—C22—H22A	110.0
C14—C13—H13	120.3	C18—C22—H22B	110.0
C12—C13—H13	120.3	C21—C22—H22B	110.0
O2—C14—C13	124.00 (16)	H22A—C22—H22B	108.4
O2—C14—C15	115.25 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7i	0.88	2.38	3.155 (2)	147
C17—H17A···O3ii	0.98	2.44	3.216 (3)	136
C8—H8···Cgi	0.95	2.72	3.506 (2)	142
C21—H21B···Cgiii	0.99	2.93	3.904 (3)	169

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	2.38	3.155 (2)	147
C17—H17A⋯O3ii	0.98	2.44	3.216 (3)	136
C8—H8⋯Cg i	0.95	2.72	3.506 (2)	142
C21—H21B⋯Cg iii	0.99	2.93	3.904 (3)	169

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