6-Benzyl-sulfanyl-9H-purine.

The phenyl ring of the title compound, C(12)H(10)N(4)S, a purine derivative, is oriented at a dihedral angle of 76.65 (6)° with respect to the purine ring system. An inter-molecular N-H⋯N hydrogen bonds stabilizes the crystal structure.

Related literature

For the biological activity of purine derivatives, see: Lepage et al. (1964 ▶); Mitsuya & Border (1986 ▶); Ragazzi et al. (1989 ▶).

Experimental

Crystal data

C12H10N4S

M = 242.30

Orthorhombic,

a = 5.5717 (3) Å

b = 9.4733 (4) Å

c = 22.4656 (14) Å

V = 1185.79 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.29 × 0.12 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.930, T max = 0.978

7941 measured reflections

2941 independent reflections

2102 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.088

S = 0.98

2941 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1207 Friedel pairs

Flack parameter: −0.09 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045140/bt5117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045140/bt5117Isup2.hkl

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

C12H10N4S	F(000) = 504
Mr = 242.30	Dx = 1.357 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2230 reflections
a = 5.5717 (3) Å	θ = 2.3–24.8°
b = 9.4733 (4) Å	µ = 0.26 mm−1
c = 22.4656 (14) Å	T = 296 K
V = 1185.79 (11) Å3	Needle, red
Z = 4	0.29 × 0.12 × 0.09 mm

Bruker Kappa APEXII CCD diffractometer	2941 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→6
Tmin = 0.930, Tmax = 0.978	k = −12→12
7941 measured reflections	l = −28→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
2941 reflections	Δρmax = 0.17 e Å−3
157 parameters	Δρmin = −0.16 e Å−3
0 restraints	Absolute structure: Flack (1983), 1207 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
S1	0.47086 (11)	0.20744 (5)	0.15044 (2)	0.05534 (18)
N1	0.3943 (4)	−0.07206 (16)	0.13660 (7)	0.0553 (5)
N2	0.6348 (4)	−0.25776 (16)	0.18001 (8)	0.0577 (5)
N3	0.9619 (4)	−0.16476 (15)	0.23955 (8)	0.0519 (5)
H3N	1.020 (4)	−0.2456 (19)	0.2541 (8)	0.062*
N4	0.8929 (3)	0.06585 (15)	0.22833 (7)	0.0488 (4)
C1	0.7639 (4)	−0.15403 (16)	0.20432 (9)	0.0454 (5)
C2	0.7219 (4)	−0.01004 (17)	0.19749 (8)	0.0432 (5)
C3	0.5298 (4)	0.02806 (17)	0.16181 (8)	0.0447 (5)
C4	0.4558 (4)	−0.2074 (2)	0.14777 (10)	0.0618 (6)
H4	0.3578	−0.2750	0.1302	0.074*
C5	1.0294 (4)	−0.03046 (17)	0.25248 (10)	0.0530 (5)
H5	1.1608	−0.0090	0.2764	0.064*
C6	0.2345 (4)	0.2002 (2)	0.09542 (10)	0.0662 (6)
H6A	0.2763	0.1328	0.0646	0.079*
H6B	0.0862	0.1694	0.1140	0.079*
C7	0.2003 (4)	0.3442 (2)	0.06836 (9)	0.0500 (5)
C8	0.3547 (5)	0.3944 (2)	0.02616 (10)	0.0646 (6)
H8	0.4883	0.3409	0.0158	0.077*
C9	0.3174 (5)	0.5222 (2)	−0.00144 (11)	0.0741 (8)
H9	0.4228	0.5532	−0.0307	0.089*
C10	0.1270 (6)	0.6027 (2)	0.01415 (12)	0.0708 (7)
H10	0.1011	0.6889	−0.0046	0.085*
C11	−0.0261 (5)	0.5576 (3)	0.05709 (12)	0.0780 (7)
H11	−0.1550	0.6139	0.0684	0.094*
C12	0.0092 (5)	0.4280 (3)	0.08406 (10)	0.0690 (6)
H12	−0.0976	0.3972	0.1131	0.083*

	U11	U22	U33	U12	U13	U23
S1	0.0640 (4)	0.0405 (3)	0.0616 (3)	−0.0021 (3)	−0.0128 (3)	0.0078 (2)
N1	0.0659 (12)	0.0470 (9)	0.0530 (11)	−0.0109 (9)	−0.0074 (9)	0.0019 (8)
N2	0.0708 (12)	0.0373 (8)	0.0650 (12)	−0.0098 (9)	−0.0048 (11)	−0.0040 (8)
N3	0.0602 (12)	0.0309 (7)	0.0647 (11)	0.0005 (8)	−0.0058 (10)	0.0064 (7)
N4	0.0571 (11)	0.0330 (7)	0.0562 (11)	−0.0034 (8)	−0.0085 (9)	0.0020 (7)
C1	0.0582 (14)	0.0303 (9)	0.0478 (11)	−0.0028 (9)	0.0053 (10)	0.0011 (8)
C2	0.0525 (13)	0.0308 (9)	0.0464 (11)	−0.0040 (9)	0.0029 (9)	0.0022 (8)
C3	0.0526 (12)	0.0386 (9)	0.0431 (11)	−0.0025 (9)	0.0044 (10)	0.0049 (8)
C4	0.0758 (16)	0.0467 (11)	0.0627 (13)	−0.0193 (12)	−0.0046 (14)	−0.0087 (11)
C5	0.0587 (14)	0.0378 (9)	0.0625 (13)	−0.0042 (10)	−0.0083 (12)	0.0024 (9)
C6	0.0704 (15)	0.0566 (12)	0.0715 (15)	−0.0128 (12)	−0.0217 (12)	0.0201 (11)
C7	0.0496 (13)	0.0480 (11)	0.0525 (13)	−0.0036 (10)	−0.0095 (10)	0.0048 (10)
C8	0.0681 (16)	0.0550 (12)	0.0705 (15)	0.0111 (11)	0.0186 (13)	0.0048 (12)
C9	0.094 (2)	0.0577 (13)	0.0710 (17)	−0.0028 (15)	0.0181 (15)	0.0168 (12)
C10	0.0819 (19)	0.0491 (12)	0.0814 (18)	0.0038 (13)	−0.0133 (16)	0.0103 (13)
C11	0.0651 (17)	0.0740 (15)	0.0948 (19)	0.0241 (15)	0.0010 (17)	−0.0048 (14)
C12	0.0568 (15)	0.0833 (15)	0.0668 (15)	−0.0018 (15)	0.0091 (13)	0.0148 (12)

S1—C3	1.7495 (17)	C6—C7	1.506 (3)
S1—C6	1.808 (2)	C6—H6A	0.9700
N1—C3	1.338 (2)	C6—H6B	0.9700
N1—C4	1.350 (3)	C7—C8	1.366 (3)
N2—C4	1.322 (3)	C7—C12	1.374 (3)
N2—C1	1.334 (2)	C8—C9	1.376 (3)
N3—C5	1.358 (2)	C8—H8	0.9300
N3—C1	1.362 (3)	C9—C10	1.352 (4)
N3—H3N	0.894 (19)	C9—H9	0.9300
N4—C5	1.306 (2)	C10—C11	1.357 (4)
N4—C2	1.380 (2)	C10—H10	0.9300
C1—C2	1.392 (2)	C11—C12	1.383 (3)
C2—C3	1.385 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—H5	0.9300
C3—S1—C6	101.51 (10)	C7—C6—H6A	109.8
C3—N1—C4	116.80 (18)	S1—C6—H6A	109.8
C4—N2—C1	111.39 (16)	C7—C6—H6B	109.8
C5—N3—C1	106.18 (16)	S1—C6—H6B	109.8
C5—N3—H3N	128.6 (13)	H6A—C6—H6B	108.2
C1—N3—H3N	124.8 (14)	C8—C7—C12	117.73 (19)
C5—N4—C2	104.28 (15)	C8—C7—C6	121.1 (2)
N2—C1—N3	128.28 (17)	C12—C7—C6	121.2 (2)
N2—C1—C2	125.9 (2)	C7—C8—C9	121.6 (2)
N3—C1—C2	105.86 (16)	C7—C8—H8	119.2
N4—C2—C3	133.49 (16)	C9—C8—H8	119.2
N4—C2—C1	109.82 (18)	C10—C9—C8	119.9 (2)
C3—C2—C1	116.67 (18)	C10—C9—H9	120.1
N1—C3—C2	119.75 (16)	C8—C9—H9	120.1
N1—C3—S1	121.40 (16)	C9—C10—C11	120.0 (2)
C2—C3—S1	118.85 (14)	C9—C10—H10	120.0
N2—C4—N1	129.52 (19)	C11—C10—H10	120.0
N2—C4—H4	115.2	C10—C11—C12	120.1 (2)
N1—C4—H4	115.2	C10—C11—H11	120.0
N4—C5—N3	113.9 (2)	C12—C11—H11	120.0
N4—C5—H5	123.1	C7—C12—C11	120.7 (2)
N3—C5—H5	123.1	C7—C12—H12	119.7
C7—C6—S1	109.51 (15)	C11—C12—H12	119.7
C4—N2—C1—N3	−179.25 (19)	C6—S1—C3—C2	173.43 (16)
C4—N2—C1—C2	−0.2 (3)	C1—N2—C4—N1	1.0 (3)
C5—N3—C1—N2	179.4 (2)	C3—N1—C4—N2	−0.8 (3)
C5—N3—C1—C2	0.2 (2)	C2—N4—C5—N3	0.4 (2)
C5—N4—C2—C3	−178.5 (2)	C1—N3—C5—N4	−0.4 (2)
C5—N4—C2—C1	−0.2 (2)	C3—S1—C6—C7	−165.98 (17)
N2—C1—C2—N4	−179.20 (19)	S1—C6—C7—C8	77.9 (2)
N3—C1—C2—N4	0.0 (2)	S1—C6—C7—C12	−103.9 (2)
N2—C1—C2—C3	−0.6 (3)	C12—C7—C8—C9	−2.2 (4)
N3—C1—C2—C3	178.62 (17)	C6—C7—C8—C9	176.1 (2)
C4—N1—C3—C2	−0.2 (3)	C7—C8—C9—C10	1.6 (4)
C4—N1—C3—S1	179.49 (15)	C8—C9—C10—C11	0.3 (4)
N4—C2—C3—N1	179.0 (2)	C9—C10—C11—C12	−1.4 (4)
C1—C2—C3—N1	0.8 (3)	C8—C7—C12—C11	1.0 (4)
N4—C2—C3—S1	−0.7 (3)	C6—C7—C12—C11	−177.3 (2)
C1—C2—C3—S1	−178.90 (15)	C10—C11—C12—C7	0.8 (4)
C6—S1—C3—N1	−6.23 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N4i	0.894 (19)	1.892 (19)	2.773 (2)	167.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N4i	0.894 (19)	1.892 (19)	2.773 (2)	167.9 (18)

Symmetry code: (i) .