Literature DB >> 25553046

Crystal structure of 1-methyl-4-methyl-sulfanyl-1H-pyrazolo-[3,4-d]pyrimidine.

Mohammed El Fal¹, Youssef Ramli², El Mokhtar Essassi¹, Mohamed Saadi³, Lahcen El Ammari³.

Abstract

In the title compound, C7H8N4S, the non-H atoms of the pyrazolo-[3,4-d]pyrimidine ring system and the methyl-sulfanyl group lie on a crystallographic mirror plane. In the crystal, mol-ecules are linked via a number of π-π inter-actions [centroid-centroid distances vary from 3.452 (7) to 3.6062 (8) Å], forming a three-dimensional structure.

Entities: Chemical Disease Species

Keywords: 1H-pyrazolo[3,4-d]pyrimidine; crystal structure; pharmacological and biochemical properties; π–π interactions

Year: 2014 PMID： 25553046 PMCID： PMC4257437 DOI： 10.1107/S1600536814025239

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For similar compounds, see: El Fal et al. (2013 ▶, 2014a ▶,b ▶); Ouzidan et al. (2011 ▶). For pharmacological and biochemical properties of pyrazolo[3,4-d]pyrimidine-4(5H)-thione derivatives, see: Chauhan & Kumar (2013 ▶); Venkatesan et al. (2014 ▶); Rashad et al. (2011 ▶).

Experimental

Crystal data

C7H8N4S M = 180.23 Orthorhombic, a = 7.9309 (14) Å b = 15.335 (3) Å c = 6.7158 (12) Å V = 816.8 (3) Å3 Z = 4 Mo Kα radiation μ = 0.34 mm−1 T = 296 K 0.37 × 0.28 × 0.19 mm

Data collection

Bruker X8 APEX diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.637, T max = 0.746 2970 measured reflections 1227 independent reflections 1017 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.129 S = 1.09 1227 reflections 73 parameters H-atom parameters constrained Δρmax = 0.44 e Å−3 Δρmin = −0.29 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/S1600536814025239/tk5348sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025239/tk5348Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814025239/tk5348Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814025239/tk5348fig1.tif Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles. CCDC reference: 1034638 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₇H₈N₄S	F(000) = 376
M_r = 180.23	D_x = 1.466 Mg m⁻³
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 1227 reflections
a = 7.9309 (14) Å	θ = 2.6–29.6°
b = 15.335 (3) Å	µ = 0.34 mm⁻¹
c = 6.7158 (12) Å	T = 296 K
V = 816.8 (3) Å³	Block, orange
Z = 4	0.37 × 0.28 × 0.19 mm

Bruker X8 APEX diffractometer	1227 independent reflections
Radiation source: fine-focus sealed tube	1017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 29.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→4
T_min = 0.637, T_max = 0.746	k = −21→19
2970 measured reflections	l = −3→9

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0694P)² + 0.3181P] where P = (F_o² + 2F_c²)/3
1227 reflections	(Δ/σ)_max < 0.001
73 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.29 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	U_iso*/U_eq
C1	0.5519 (3)	0.06804 (13)	0.2500	0.0393 (5)
H1	0.4928	0.0156	0.2500	0.047*
C2	0.5516 (3)	0.21199 (12)	0.2500	0.0279 (4)
C3	0.7675 (3)	0.30515 (13)	0.2500	0.0322 (4)
H3	0.8763	0.3277	0.2500	0.039*
C4	0.7284 (2)	0.21512 (11)	0.2500	0.0264 (4)
C5	0.8115 (3)	0.13396 (11)	0.2500	0.0285 (4)
C6	0.3247 (3)	0.32714 (15)	0.2500	0.0450 (6)
H6A	0.3121	0.3658	0.1386	0.068*
H6B	0.2414	0.2818	0.2500	0.068*
C7	1.0858 (3)	0.02097 (16)	0.2500	0.0483 (6)
H7A	0.9865	−0.0148	0.2500	0.072*
H7B	1.1499	0.0095	0.1316	0.072*
N1	0.7221 (2)	0.06053 (10)	0.2500	0.0348 (4)
N2	0.4577 (2)	0.13910 (11)	0.2500	0.0369 (4)
N3	0.4970 (2)	0.29563 (11)	0.2500	0.0323 (4)
N4	0.6289 (3)	0.35277 (10)	0.2500	0.0349 (4)
S1	1.03110 (7)	0.13414 (4)	0.2500	0.0447 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0316 (10)	0.0218 (9)	0.0644 (15)	−0.0024 (7)	0.000	0.000
C2	0.0294 (9)	0.0221 (8)	0.0321 (9)	0.0016 (7)	0.000	0.000
C3	0.0301 (10)	0.0230 (8)	0.0434 (11)	−0.0032 (7)	0.000	0.000
C4	0.0280 (9)	0.0216 (8)	0.0295 (9)	−0.0008 (6)	0.000	0.000
C5	0.0295 (9)	0.0232 (9)	0.0329 (9)	0.0005 (7)	0.000	0.000
C6	0.0329 (11)	0.0330 (11)	0.0692 (16)	0.0095 (9)	0.000	0.000
C7	0.0376 (12)	0.0393 (12)	0.0680 (17)	0.0119 (10)	0.000	0.000
N1	0.0307 (9)	0.0199 (7)	0.0536 (11)	0.0005 (6)	0.000	0.000
N2	0.0290 (9)	0.0250 (9)	0.0568 (12)	−0.0015 (6)	0.000	0.000
N3	0.0318 (8)	0.0221 (7)	0.0429 (9)	0.0024 (6)	0.000	0.000
N4	0.0399 (10)	0.0211 (7)	0.0439 (10)	−0.0021 (6)	0.000	0.000
S1	0.0264 (3)	0.0316 (3)	0.0761 (5)	0.00110 (18)	0.000	0.000

C1—N2	1.321 (3)	C5—N1	1.331 (2)
C1—N1	1.355 (3)	C5—S1	1.741 (2)
C1—H1	0.9300	C6—N3	1.449 (3)
C2—N2	1.343 (3)	C6—H6A	0.9598
C2—N3	1.354 (2)	C6—H6B	0.9599
C2—C4	1.403 (3)	C7—S1	1.789 (3)
C3—N4	1.319 (3)	C7—H7A	0.9600
C3—C4	1.415 (2)	C7—H7B	0.9599
C3—H3	0.9300	N3—N4	1.365 (3)
C4—C5	1.408 (2)

N2—C1—N1	129.3 (2)	C4—C5—S1	117.82 (14)
N2—C1—H1	115.3	N3—C6—H6A	107.7
N1—C1—H1	115.3	N3—C6—H6B	114.1
N2—C2—N3	127.68 (18)	H6A—C6—H6B	112.1
N2—C2—C4	125.63 (18)	S1—C7—H7A	110.8
N3—C2—C4	106.69 (17)	S1—C7—H7B	107.8
N4—C3—C4	110.97 (17)	H7A—C7—H7B	109.3
N4—C3—H3	124.5	C5—N1—C1	117.33 (17)
C4—C3—H3	124.5	C1—N2—C2	111.89 (18)
C2—C4—C5	115.96 (17)	C2—N3—N4	111.29 (17)
C2—C4—C3	104.60 (16)	C2—N3—C6	128.13 (19)
C5—C4—C3	139.45 (19)	N4—N3—C6	120.59 (17)
N1—C5—C4	119.88 (19)	C3—N4—N3	106.45 (16)
N1—C5—S1	122.30 (14)	C5—S1—C7	103.95 (11)

9 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells.

Authors: Aymn E Rashad; Abeer E Mahmoud; Mamdouh M Ali
Journal: Eur J Med Chem Date: 2011-01-15 Impact factor: 6.514

3. Discovery of simplified N²-substituted pyrazolo[3,4-d]pyrimidine derivatives as novel adenosine receptor antagonists: efficient synthetic approaches, biological evaluations and molecular docking studies.

Authors: Gopalakrishnan Venkatesan; Priyankar Paira; Siew Lee Cheong; Kosaraju Vamsikrishna; Stephanie Federico; Karl-Norbert Klotz; Giampiero Spalluto; Giorgia Pastorin
Journal: Bioorg Med Chem Date: 2014-01-31 Impact factor: 3.641

Crystal structure of 1-methyl-4-methyl-sulfanyl-1H-pyrazolo-[3,4-d]pyrimidine.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells.

3. Discovery of simplified N²-substituted pyrazolo[3,4-d]pyrimidine derivatives as novel adenosine receptor antagonists: efficient synthetic approaches, biological evaluations and molecular docking studies.

Review 4. Medicinal attributes of pyrazolo[3,4-d]pyrimidines: a review.

5. 1-Benzyl-1H-benzimidazol-2(3H)-one.

6. 4-Benzyl-sulfanyl-1H-pyrazolo-[3,4-d]pyrimidine.

7. Structure validation in chemical crystallography.

8. Crystal structure of 4-allyl-sulfanyl-1H-pyrazolo-[3,4-d]pyrimidine.

9. Crystal structure of 1-ethyl-pyrazolo[3,4-d]pyrimidine-4(5H)-thione.