Crystal structure of 4,6-bis­[(E)-4-bromo­styr­yl]-2-(butyl­sulfan­yl)pyrimidine

Wang Yu; Jingbao Song; Aijian Wang

doi:10.1107/S1600536814024714

. 2014 Nov 21;70(Pt 12):o1282. doi: 10.1107/S1600536814024714

Crystal structure of 4,6-bis[(E)-4-bromostyryl]-2-(butylsulfanyl)pyrimidine

Wang Yu ^a, Jingbao Song ^a, Aijian Wang ^a,^*

PMCID: PMC4257452 PMID: 25553047

Abstract

In the title compound, C₂₄H₂₂Br₂N₂S, the dihedral angles between the central pyrimidine ring and the pendant bromobenzene rings are 11.02 (11) and 13.20 (12)°. The butyl side chain adopts a gauche conformation [C—C—C—C = −67.4 (4)°]. In the crystal, weak aromatic π–π stacking is observed between the pyrimidine ring and one of the benzene rings [centroid–centroid separation = 3.6718 (17) Å].

Keywords: crystal structure, weak interaction, pyrimidine

Related literature

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009 ▶); van Laar et al. (2001 ▶); Joule & Mills (2000 ▶); Deng et al. (2008 ▶); Nguyen (2008 ▶). For further synthetic details, see: Liu et al. (2007 ▶).

Experimental

Crystal data

C₂₄H₂₂Br₂N₂S
M _r = 530.32
Monoclinic,
a = 9.5636 (19) Å
b = 10.630 (2) Å
c = 23.708 (6) Å
β = 112.82 (3)°
V = 2221.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 3.76 mm⁻¹
T = 153 K
0.24 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.728, T _max = 1.000
10036 measured reflections
4043 independent reflections
3601 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.066
S = 1.04
4043 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814024714/hb7313sup1.cif

e-70-o1282-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024714/hb7313Isup2.hkl

e-70-o1282-Isup2.hkl^{(198.2KB, hkl)}

Click here for additional data file.^{(3.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814024714/hb7313Isup3.cml

Click here for additional data file.^{(779.5KB, doc)}

Supporting information file. DOI: 10.1107/S1600536814024714/hb7313Isup4.doc

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S1600536814024714/hb7313fig1.tif

The molecular structure of (I) showing 50% displacement ellipsoids.

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S1600536814024714/hb7313fig2.tif

Packing diagram for (I)

CCDC reference: 1010673

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was supported financially by the Research Foundation of Jiangsu University (13JDG066).

supplementary crystallographic information

S1. Experimental

S1.1. Synthesis and crystallization

2-(Butylthio)-4,6-dimethylpyrimidine (2.95 g, 15 mmol) and bromobenzaldehyde (6.1 g, 33 mmol) were added in an aqueous solution of sodium hydroxide (5 M, 50 ml) containing tetrabutylammonium iodide (10 mol % versus the heterocycle) and mixed. The mixture was heated under reflux for 3 h. After cooling, the reaction mixture was extracted with dichloromethane (120 ml × 3). The extract solution was dried with magnesium sulfate. After removal of the drying agent by filtration, the solvent was removed by evaporation under reduced pressure. The crude product was recrystallized to afford yellow prisms of the title compound, (I) (5.17 g, yield 65%).

S1.2. Refinement

S2. Results and discussion