4-Benzyl-sulfanyl-1H-pyrazolo-[3,4-d]pyrimidine.

The pyrazolo-[3,4-d]pyrimidine ring system of the title compound, C12H10N4S, is essentially planar [maximum deviation = 0.025 (1) Å for the C atom bearing the S atom] and almost perpendicular to the phenyl ring [dihedral angle = 71.42 (6)°]. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers.

Related literature

For the biological properties of pyrazolo­[3,4-d]pyrimidine derivatives, see: Rashad et al. (2008 ▶, 2011 ▶); Ballell et al. (2007 ▶). For related compounds, see: Moussaif et al. (2010 ▶); Ouzidan et al. (2011 ▶); Alsubari et al. (2011 ▶).

Experimental

Crystal data

C12H10N4S

M = 242.30

Monoclinic,

a = 9.4737 (3) Å

b = 5.1709 (2) Å

c = 23.6159 (8) Å

β = 96.823 (1)°

V = 1148.69 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.42 × 0.29 × 0.17 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.991

15333 measured reflections

3509 independent reflections

2885 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.03

3509 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302789X/rz5086sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302789X/rz5086Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302789X/rz5086Isup3.cml

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

C12H10N4S	F(000) = 504
Mr = 242.30	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3509 reflections
a = 9.4737 (3) Å	θ = 2.6–30.5°
b = 5.1709 (2) Å	µ = 0.26 mm−1
c = 23.6159 (8) Å	T = 296 K
β = 96.823 (1)°	Sheet, yellow
V = 1148.69 (7) Å3	0.42 × 0.29 × 0.17 mm
Z = 4

Bruker X8 APEXII diffractometer	3509 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
Tmin = 0.960, Tmax = 0.991	k = −7→7
15333 measured reflections	l = −33→33

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2818P] where P = (Fo2 + 2Fc2)/3
3509 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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 > 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
C1	0.53146 (14)	0.5891 (3)	0.39990 (6)	0.0400 (3)
H1	0.6186	0.6093	0.3860	0.048*
C2	0.38176 (14)	0.7002 (2)	0.46100 (5)	0.0347 (3)
C3	0.17220 (16)	0.5324 (3)	0.47363 (7)	0.0510 (4)
H3	0.0914	0.4289	0.4698	0.061*
C4	0.28477 (13)	0.5093 (2)	0.43999 (5)	0.0349 (3)
C5	0.32168 (12)	0.3638 (2)	0.39401 (5)	0.0315 (2)
C6	0.28394 (15)	0.0099 (3)	0.30385 (6)	0.0416 (3)
H6A	0.3863	0.0157	0.3134	0.050*
H6B	0.2568	−0.1699	0.2979	0.050*
C7	0.24460 (14)	0.1560 (2)	0.24936 (6)	0.0369 (3)
C8	0.12518 (16)	0.0842 (3)	0.21266 (6)	0.0467 (3)
H8	0.0701	−0.0551	0.2219	0.056*
C9	0.08797 (17)	0.2192 (4)	0.16251 (7)	0.0555 (4)
H9	0.0086	0.1683	0.1380	0.067*
C10	0.16673 (19)	0.4269 (4)	0.14851 (7)	0.0566 (4)
H10	0.1402	0.5183	0.1150	0.068*
C11	0.28603 (18)	0.4997 (3)	0.18457 (7)	0.0534 (4)
H11	0.3401	0.6400	0.1752	0.064*
C12	0.32523 (16)	0.3646 (3)	0.23458 (6)	0.0450 (3)
H12	0.4060	0.4136	0.2584	0.054*
N1	0.44627 (11)	0.4023 (2)	0.37454 (5)	0.0371 (2)
N2	0.50762 (11)	0.7469 (2)	0.44184 (5)	0.0385 (2)
N3	0.32520 (13)	0.8224 (2)	0.50327 (5)	0.0456 (3)
H3N	0.3651	0.9487	0.5227	0.055*
N4	0.19642 (15)	0.7201 (3)	0.51134 (6)	0.0583 (4)
S1	0.20019 (4)	0.13646 (7)	0.363530 (14)	0.04065 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0380 (6)	0.0415 (7)	0.0407 (7)	−0.0091 (5)	0.0060 (5)	−0.0020 (5)
C2	0.0405 (6)	0.0316 (6)	0.0305 (5)	−0.0006 (5)	−0.0017 (4)	−0.0004 (4)
C3	0.0425 (7)	0.0646 (10)	0.0478 (8)	−0.0093 (7)	0.0126 (6)	−0.0170 (7)
C4	0.0351 (6)	0.0369 (6)	0.0321 (6)	−0.0032 (5)	0.0020 (4)	−0.0023 (5)
C5	0.0335 (6)	0.0297 (5)	0.0301 (5)	−0.0011 (4)	−0.0007 (4)	0.0009 (4)
C6	0.0476 (7)	0.0327 (6)	0.0432 (7)	0.0040 (5)	−0.0008 (5)	−0.0070 (5)
C7	0.0396 (6)	0.0322 (6)	0.0388 (6)	0.0053 (5)	0.0044 (5)	−0.0080 (5)
C8	0.0434 (7)	0.0441 (7)	0.0506 (8)	0.0005 (6)	−0.0025 (6)	−0.0039 (6)
C9	0.0476 (8)	0.0655 (10)	0.0505 (8)	0.0123 (8)	−0.0060 (6)	−0.0025 (8)
C10	0.0608 (9)	0.0641 (10)	0.0464 (8)	0.0263 (8)	0.0126 (7)	0.0104 (7)
C11	0.0598 (9)	0.0468 (8)	0.0576 (9)	0.0059 (7)	0.0231 (7)	0.0055 (7)
C12	0.0445 (7)	0.0435 (8)	0.0480 (8)	−0.0009 (6)	0.0091 (6)	−0.0068 (6)
N1	0.0368 (5)	0.0373 (6)	0.0373 (5)	−0.0044 (4)	0.0050 (4)	−0.0037 (4)
N2	0.0421 (6)	0.0349 (6)	0.0377 (5)	−0.0080 (5)	0.0008 (4)	−0.0010 (4)
N3	0.0506 (7)	0.0457 (6)	0.0401 (6)	−0.0053 (5)	0.0040 (5)	−0.0130 (5)
N4	0.0521 (7)	0.0715 (9)	0.0535 (8)	−0.0077 (7)	0.0158 (6)	−0.0225 (7)
S1	0.03936 (18)	0.0419 (2)	0.04027 (18)	−0.01091 (13)	0.00279 (12)	−0.00697 (13)

C1—N2	1.3234 (17)	C6—H6B	0.9700
C1—N1	1.3521 (17)	C7—C12	1.390 (2)
C1—H1	0.9300	C7—C8	1.3914 (19)
C2—N3	1.3455 (17)	C8—C9	1.384 (2)
C2—N2	1.3464 (17)	C8—H8	0.9300
C2—C4	1.3988 (17)	C9—C10	1.371 (3)
C3—N4	1.319 (2)	C9—H9	0.9300
C3—C4	1.4085 (19)	C10—C11	1.384 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.3992 (17)	C11—C12	1.385 (2)
C5—N1	1.3316 (16)	C11—H11	0.9300
C5—S1	1.7399 (12)	C12—H12	0.9300
C6—C7	1.5008 (19)	N3—N4	1.3637 (18)
C6—S1	1.8193 (14)	N3—H3N	0.8600
C6—H6A	0.9700
N2—C1—N1	128.77 (12)	C8—C7—C6	120.02 (13)
N2—C1—H1	115.6	C9—C8—C7	120.27 (15)
N1—C1—H1	115.6	C9—C8—H8	119.9
N3—C2—N2	127.71 (12)	C7—C8—H8	119.9
N3—C2—C4	106.97 (12)	C10—C9—C8	120.74 (15)
N2—C2—C4	125.32 (12)	C10—C9—H9	119.6
N4—C3—C4	111.15 (13)	C8—C9—H9	119.6
N4—C3—H3	124.4	C9—C10—C11	119.54 (15)
C4—C3—H3	124.4	C9—C10—H10	120.2
C2—C4—C5	116.14 (11)	C11—C10—H10	120.2
C2—C4—C3	104.44 (11)	C10—C11—C12	120.27 (16)
C5—C4—C3	139.39 (12)	C10—C11—H11	119.9
N1—C5—C4	120.07 (11)	C12—C11—H11	119.9
N1—C5—S1	121.88 (9)	C11—C12—C7	120.41 (14)
C4—C5—S1	118.05 (9)	C11—C12—H12	119.8
C7—C6—S1	113.35 (9)	C7—C12—H12	119.8
C7—C6—H6A	108.9	C5—N1—C1	117.44 (11)
S1—C6—H6A	108.9	C1—N2—C2	112.17 (11)
C7—C6—H6B	108.9	C2—N3—N4	111.31 (12)
S1—C6—H6B	108.9	C2—N3—H3N	124.3
H6A—C6—H6B	107.7	N4—N3—H3N	124.3
C12—C7—C8	118.76 (14)	C3—N4—N3	106.12 (12)
C12—C7—C6	121.21 (12)	C5—S1—C6	103.63 (6)
N3—C2—C4—C5	178.01 (11)	C10—C11—C12—C7	−0.6 (2)
N2—C2—C4—C5	−2.39 (19)	C8—C7—C12—C11	0.8 (2)
N3—C2—C4—C3	−0.53 (15)	C6—C7—C12—C11	−178.96 (13)
N2—C2—C4—C3	179.08 (13)	C4—C5—N1—C1	−1.62 (18)
N4—C3—C4—C2	0.49 (18)	S1—C5—N1—C1	177.92 (10)
N4—C3—C4—C5	−177.49 (16)	N2—C1—N1—C5	−1.3 (2)
C2—C4—C5—N1	3.22 (17)	N1—C1—N2—C2	2.1 (2)
C3—C4—C5—N1	−178.96 (17)	N3—C2—N2—C1	179.40 (13)
C2—C4—C5—S1	−176.34 (9)	C4—C2—N2—C1	−0.13 (18)
C3—C4—C5—S1	1.5 (2)	N2—C2—N3—N4	−179.18 (13)
S1—C6—C7—C12	90.97 (14)	C4—C2—N3—N4	0.42 (16)
S1—C6—C7—C8	−88.78 (14)	C4—C3—N4—N3	−0.2 (2)
C12—C7—C8—C9	−0.1 (2)	C2—N3—N4—C3	−0.11 (19)
C6—C7—C8—C9	179.65 (13)	N1—C5—S1—C6	−3.06 (12)
C7—C8—C9—C10	−0.8 (2)	C4—C5—S1—C6	176.49 (10)
C8—C9—C10—C11	1.0 (2)	C7—C6—S1—C5	−90.38 (11)
C9—C10—C11—C12	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N2i	0.86	2.10	2.9429 (16)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N2i	0.86	2.10	2.9429 (16)	168

Symmetry code: (i) .