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

aChina–Australia Joint Research Center for Functional Molecular Materials, Scientific Research Academy & School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
*Correspondence e-mail: wajujs@ujs.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 November 2014; accepted 11 November 2014; online 21 November 2014)

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 ππ stacking is observed between the pyrimidine ring and one of the benzene rings [centroid–centroid separation = 3.6718 (17) Å].

1. Related literature

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009[Walker, S. R., Carter, E. J., Huff, B. C. & Morris, J. C. (2009). Chem. Rev. 109, 3080-3098.]); van Laar et al. (2001[Laar, M. van, Volkerts, E. & Verbaten, M. (2001). Psychopharmacology, 154, 189-197.]); Joule & Mills (2000[Joule, J. A. & Mills, K. (2000). Heterocyclic Chemistry, 4th ed. Cambridge: Blackwell Science.]); Deng et al. (2008[Deng, Y., Wang, Y., Cherian, C., Hou, Z., Buck, S. A., Matherly, L. H. & Gangjee, A. (2008). J. Med. Chem. 51, 5052-5063.]); Nguyen (2008[Nguyen, T. L. (2008). Anticancer Agents Med. Chem. 8, 710-716.]). For further synthetic details, see: Liu et al. (2007[Liu, B., Hu, X.., Liu, J., Zhao, Y. & Huang, Z. (2007). Tetrahedron Lett. 48, 5958-5962.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C24H22Br2N2S

  • Mr = 530.32

  • Monoclinic, P 21 /c

  • 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

2.2. Data collection

  • Rigaku Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.728, Tmax = 1.000

  • 10036 measured reflections

  • 4043 independent reflections

  • 3601 reflections with I > 2σ(I)

  • Rint = 0.022

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.066

  • S = 1.04

  • 4043 reflections

  • 263 parameters

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Experimental top

Synthesis and crystallization top

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%).

Refinement top

Results and discussion top

Related literature top

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).

Computing details top

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

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

Packing diagram for (I)
4,6-Bis[(E)-4-bromostyryl]-2-(butylsulfanyl)pyrimidine top
Crystal data top
C24H22Br2N2SF(000) = 1064
Mr = 530.32Dx = 1.586 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.5636 (19) ÅCell parameters from 9235 reflections
b = 10.630 (2) Åθ = 2.9–29.2°
c = 23.708 (6) ŵ = 3.76 mm1
β = 112.82 (3)°T = 153 K
V = 2221.5 (10) Å3Prism, yellow
Z = 40.24 × 0.22 × 0.20 mm
Data collection top
Rigaku Saturn724+
diffractometer
4043 independent reflections
Radiation source: fine-focus sealed tube3601 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
h = 119
Tmin = 0.728, Tmax = 1.000k = 1211
10036 measured reflectionsl = 1928
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0344P)2 + 0.2887P]
where P = (Fo2 + 2Fc2)/3
4043 reflections(Δ/σ)max = 0.002
263 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C24H22Br2N2SV = 2221.5 (10) Å3
Mr = 530.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.5636 (19) ŵ = 3.76 mm1
b = 10.630 (2) ÅT = 153 K
c = 23.708 (6) Å0.24 × 0.22 × 0.20 mm
β = 112.82 (3)°
Data collection top
Rigaku Saturn724+
diffractometer
4043 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
3601 reflections with I > 2σ(I)
Tmin = 0.728, Tmax = 1.000Rint = 0.022
10036 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.04Δρmax = 0.68 e Å3
4043 reflectionsΔρmin = 0.38 e Å3
263 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.45970 (3)0.41644 (2)1.234842 (12)0.03454 (9)
Br21.07815 (3)0.96352 (2)0.907769 (15)0.04347 (11)
C10.3098 (3)0.3035 (2)0.92713 (11)0.0229 (5)
C20.5517 (3)0.3754 (2)0.96667 (11)0.0217 (5)
C30.5857 (3)0.2828 (2)1.01093 (11)0.0249 (5)
H30.68380.27481.04030.030*
C40.4721 (3)0.2021 (2)1.01114 (11)0.0224 (5)
C50.5015 (3)0.1044 (2)1.05768 (11)0.0250 (5)
H50.60180.08891.08340.030*
C60.3944 (3)0.0364 (2)1.06569 (11)0.0237 (5)
H60.29470.05591.04070.028*
C70.4157 (3)0.0662 (2)1.10957 (11)0.0224 (5)
C80.2879 (3)0.1289 (2)1.10968 (11)0.0264 (5)
H80.19220.10091.08400.032*
C90.2998 (3)0.2319 (2)1.14709 (11)0.0281 (6)
H90.21350.27361.14620.034*
C100.4420 (3)0.2715 (2)1.18561 (11)0.0249 (5)
C110.5712 (3)0.2086 (2)1.18849 (11)0.0264 (5)
H110.66630.23461.21570.032*
C120.5576 (3)0.1069 (2)1.15050 (11)0.0249 (5)
H120.64440.06481.15220.030*
C130.6671 (3)0.4638 (2)0.96501 (11)0.0235 (5)
H130.76240.46020.99670.028*
C140.6451 (3)0.5488 (2)0.92140 (11)0.0239 (5)
H140.54990.54940.88960.029*
C150.7548 (3)0.6417 (2)0.91800 (11)0.0232 (5)
C160.7173 (3)0.7171 (2)0.86599 (11)0.0262 (5)
H160.62530.70410.83330.031*
C170.8135 (3)0.8107 (2)0.86184 (12)0.0289 (6)
H170.78660.86030.82690.035*
C180.9497 (3)0.8291 (2)0.91031 (12)0.0271 (6)
C190.9919 (3)0.7544 (2)0.96202 (12)0.0305 (6)
H191.08540.76640.99400.037*
C200.8949 (3)0.6622 (2)0.96584 (11)0.0268 (5)
H200.92320.61271.00090.032*
C210.1228 (3)0.4306 (2)0.82034 (13)0.0367 (7)
H21A0.22340.43810.81980.044*
H21B0.05280.41080.77910.044*
C220.0793 (4)0.5525 (3)0.83894 (15)0.0501 (8)
H22A0.15380.57570.87890.060*
H22B0.01790.54340.84250.060*
C230.0681 (4)0.6585 (3)0.79286 (17)0.0578 (9)
H23A0.00010.63180.75240.069*
H23B0.02410.73230.80370.069*
C240.2172 (4)0.6943 (3)0.79049 (17)0.0617 (9)
H24A0.28920.71130.83110.093*
H24B0.20430.76800.76560.093*
H24C0.25350.62630.77320.093*
S10.12232 (7)0.30281 (6)0.87109 (3)0.03603 (18)
N10.4088 (2)0.38747 (17)0.92361 (9)0.0227 (4)
N20.3308 (2)0.21138 (17)0.96785 (9)0.0227 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04852 (18)0.02501 (14)0.03030 (16)0.00198 (12)0.01552 (13)0.00624 (10)
Br20.03001 (16)0.02807 (16)0.0752 (2)0.00696 (12)0.02359 (15)0.00722 (13)
C10.0247 (12)0.0208 (12)0.0245 (13)0.0002 (11)0.0111 (10)0.0011 (10)
C20.0242 (13)0.0178 (11)0.0265 (13)0.0001 (10)0.0138 (11)0.0024 (10)
C30.0227 (12)0.0242 (12)0.0271 (14)0.0013 (11)0.0089 (10)0.0017 (10)
C40.0270 (13)0.0185 (11)0.0255 (13)0.0015 (11)0.0143 (11)0.0006 (10)
C50.0255 (13)0.0234 (12)0.0254 (14)0.0029 (11)0.0089 (11)0.0038 (10)
C60.0273 (13)0.0215 (12)0.0233 (13)0.0011 (11)0.0110 (11)0.0012 (10)
C70.0293 (13)0.0180 (11)0.0220 (13)0.0006 (10)0.0122 (11)0.0026 (9)
C80.0241 (13)0.0278 (13)0.0272 (14)0.0002 (11)0.0099 (11)0.0014 (10)
C90.0302 (14)0.0290 (13)0.0300 (14)0.0056 (12)0.0170 (12)0.0002 (11)
C100.0370 (14)0.0200 (12)0.0214 (13)0.0017 (11)0.0153 (11)0.0006 (10)
C110.0286 (13)0.0246 (12)0.0243 (13)0.0043 (11)0.0084 (11)0.0006 (10)
C120.0286 (13)0.0221 (12)0.0265 (14)0.0037 (11)0.0134 (11)0.0010 (10)
C130.0217 (12)0.0229 (12)0.0271 (14)0.0032 (10)0.0106 (11)0.0029 (10)
C140.0241 (12)0.0237 (12)0.0248 (13)0.0028 (11)0.0104 (10)0.0031 (10)
C150.0268 (13)0.0187 (12)0.0274 (14)0.0029 (10)0.0141 (11)0.0036 (10)
C160.0263 (13)0.0235 (12)0.0264 (14)0.0022 (11)0.0078 (11)0.0003 (10)
C170.0316 (14)0.0237 (13)0.0342 (15)0.0009 (11)0.0159 (12)0.0048 (10)
C180.0251 (13)0.0185 (12)0.0429 (16)0.0034 (11)0.0189 (12)0.0000 (11)
C190.0218 (12)0.0313 (14)0.0358 (16)0.0043 (12)0.0084 (11)0.0048 (11)
C200.0265 (13)0.0268 (13)0.0261 (14)0.0011 (11)0.0092 (11)0.0031 (10)
C210.0338 (15)0.0372 (15)0.0325 (16)0.0050 (13)0.0055 (12)0.0049 (12)
C220.061 (2)0.0488 (18)0.054 (2)0.0073 (16)0.0371 (17)0.0083 (15)
C230.073 (2)0.0448 (18)0.067 (2)0.0212 (17)0.0398 (19)0.0228 (17)
C240.075 (2)0.0504 (19)0.073 (3)0.0016 (18)0.043 (2)0.0210 (17)
S10.0271 (3)0.0365 (4)0.0372 (4)0.0085 (3)0.0044 (3)0.0112 (3)
N10.0244 (11)0.0200 (10)0.0244 (11)0.0030 (9)0.0103 (9)0.0004 (8)
N20.0252 (11)0.0202 (10)0.0244 (11)0.0023 (8)0.0114 (9)0.0020 (8)
Geometric parameters (Å, º) top
Br1—C101.901 (2)C13—H130.9300
Br2—C181.901 (2)C14—C151.466 (3)
C1—N11.328 (3)C14—H140.9300
C1—N21.334 (3)C15—C161.395 (3)
C1—S11.770 (2)C15—C201.397 (3)
C2—N11.358 (3)C16—C171.385 (3)
C2—C31.382 (3)C16—H160.9300
C2—C131.462 (3)C17—C181.376 (3)
C3—C41.386 (3)C17—H170.9300
C3—H30.9300C18—C191.383 (3)
C4—N21.347 (3)C19—C201.376 (3)
C4—C51.461 (3)C19—H190.9300
C5—C61.326 (3)C20—H200.9300
C5—H50.9300C21—C221.479 (4)
C6—C71.466 (3)C21—S11.816 (3)
C6—H60.9300C21—H21A0.9700
C7—C81.393 (3)C21—H21B0.9700
C7—C121.396 (3)C22—C231.544 (4)
C8—C91.386 (3)C22—H22A0.9700
C8—H80.9300C22—H22B0.9700
C9—C101.377 (3)C23—C241.497 (4)
C9—H90.9300C23—H23A0.9700
C10—C111.383 (3)C23—H23B0.9700
C11—C121.381 (3)C24—H24A0.9600
C11—H110.9300C24—H24B0.9600
C12—H120.9300C24—H24C0.9600
C13—C141.327 (3)
N1—C1—N2128.9 (2)C20—C15—C14122.8 (2)
N1—C1—S1119.68 (17)C17—C16—C15121.7 (2)
N2—C1—S1111.38 (17)C17—C16—H16119.2
N1—C2—C3120.7 (2)C15—C16—H16119.2
N1—C2—C13118.0 (2)C18—C17—C16118.9 (2)
C3—C2—C13121.3 (2)C18—C17—H17120.6
C2—C3—C4119.3 (2)C16—C17—H17120.6
C2—C3—H3120.3C17—C18—C19121.0 (2)
C4—C3—H3120.3C17—C18—Br2119.62 (19)
N2—C4—C3120.6 (2)C19—C18—Br2119.33 (19)
N2—C4—C5118.0 (2)C20—C19—C18119.6 (2)
C3—C4—C5121.4 (2)C20—C19—H19120.2
C6—C5—C4124.3 (2)C18—C19—H19120.2
C6—C5—H5117.9C19—C20—C15121.1 (2)
C4—C5—H5117.9C19—C20—H20119.4
C5—C6—C7127.2 (2)C15—C20—H20119.4
C5—C6—H6116.4C22—C21—S1112.6 (2)
C7—C6—H6116.4C22—C21—H21A109.1
C8—C7—C12117.9 (2)S1—C21—H21A109.1
C8—C7—C6118.5 (2)C22—C21—H21B109.1
C12—C7—C6123.7 (2)S1—C21—H21B109.1
C9—C8—C7121.6 (2)H21A—C21—H21B107.8
C9—C8—H8119.2C21—C22—C23112.3 (3)
C7—C8—H8119.2C21—C22—H22A109.2
C10—C9—C8118.7 (2)C23—C22—H22A109.2
C10—C9—H9120.6C21—C22—H22B109.2
C8—C9—H9120.6C23—C22—H22B109.2
C9—C10—C11121.3 (2)H22A—C22—H22B107.9
C9—C10—Br1118.99 (18)C24—C23—C22113.9 (3)
C11—C10—Br1119.76 (18)C24—C23—H23A108.8
C12—C11—C10119.3 (2)C22—C23—H23A108.8
C12—C11—H11120.3C24—C23—H23B108.8
C10—C11—H11120.3C22—C23—H23B108.8
C11—C12—C7121.1 (2)H23A—C23—H23B107.7
C11—C12—H12119.5C23—C24—H24A109.5
C7—C12—H12119.5C23—C24—H24B109.5
C14—C13—C2124.4 (2)H24A—C24—H24B109.5
C14—C13—H13117.8C23—C24—H24C109.5
C2—C13—H13117.8H24A—C24—H24C109.5
C13—C14—C15127.0 (2)H24B—C24—H24C109.5
C13—C14—H14116.5C1—S1—C21103.43 (12)
C15—C14—H14116.5C1—N1—C2115.05 (19)
C16—C15—C20117.7 (2)C1—N2—C4115.4 (2)
C16—C15—C14119.4 (2)
N1—C2—C3—C40.1 (3)C20—C15—C16—C171.1 (4)
C13—C2—C3—C4179.2 (2)C14—C15—C16—C17176.6 (2)
C2—C3—C4—N21.6 (3)C15—C16—C17—C180.2 (4)
C2—C3—C4—C5178.7 (2)C16—C17—C18—C191.2 (4)
N2—C4—C5—C610.4 (3)C16—C17—C18—Br2176.17 (18)
C3—C4—C5—C6170.0 (2)C17—C18—C19—C201.6 (4)
C4—C5—C6—C7177.3 (2)Br2—C18—C19—C20175.71 (18)
C5—C6—C7—C8178.2 (2)C18—C19—C20—C150.7 (4)
C5—C6—C7—C120.3 (4)C16—C15—C20—C190.6 (4)
C12—C7—C8—C92.8 (3)C14—C15—C20—C19177.0 (2)
C6—C7—C8—C9175.8 (2)S1—C21—C22—C23175.6 (2)
C7—C8—C9—C101.0 (4)C21—C22—C23—C2467.4 (4)
C8—C9—C10—C111.6 (4)N1—C1—S1—C210.2 (2)
C8—C9—C10—Br1177.69 (18)N2—C1—S1—C21178.25 (17)
C9—C10—C11—C122.2 (3)C22—C21—S1—C190.2 (2)
Br1—C10—C11—C12177.02 (18)N2—C1—N1—C21.8 (3)
C10—C11—C12—C70.3 (3)S1—C1—N1—C2176.31 (16)
C8—C7—C12—C112.1 (3)C3—C2—N1—C11.4 (3)
C6—C7—C12—C11176.4 (2)C13—C2—N1—C1179.2 (2)
N1—C2—C13—C145.7 (3)N1—C1—N2—C40.4 (3)
C3—C2—C13—C14174.9 (2)S1—C1—N2—C4177.84 (16)
C2—C13—C14—C15178.4 (2)C3—C4—N2—C11.4 (3)
C13—C14—C15—C16174.3 (2)C5—C4—N2—C1179.0 (2)
C13—C14—C15—C208.1 (4)

Experimental details

Crystal data
Chemical formulaC24H22Br2N2S
Mr530.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)9.5636 (19), 10.630 (2), 23.708 (6)
β (°) 112.82 (3)
V3)2221.5 (10)
Z4
Radiation typeMo Kα
µ (mm1)3.76
Crystal size (mm)0.24 × 0.22 × 0.20
Data collection
DiffractometerRigaku Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2008)
Tmin, Tmax0.728, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
10036, 4043, 3601
Rint0.022
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.066, 1.04
No. of reflections4043
No. of parameters263
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.38

Computer programs: CrystalClear (Rigaku, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

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