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

Yu, W.; Song, J.; Wang, A.

doi:10.1107/S1600536814024714

organic compounds

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Volume 70| Part 12| December 2014| Page o1282

doi:10.1107/S1600536814024714

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

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

^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 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.

CCDC reference: 1010673

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₄H₂₂Br₂N₂S
M_r = 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 ) T_min = 0.728, T_max = 1.000
10036 measured reflections
4043 independent reflections
3601 reflections with I > 2σ(I)
R_int = 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
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.

Supporting information

CCDC reference: 1010673

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814024714/hb7313sup1.cif

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

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

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

checkCIF report

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

C₂₄H₂₂Br₂N₂S	F(000) = 1064
M_r = 530.32	D_x = 1.586 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5636 (19) Å	Cell parameters from 9235 reflections
b = 10.630 (2) Å	θ = 2.9–29.2°
c = 23.708 (6) Å	µ = 3.76 mm⁻¹
β = 112.82 (3)°	T = 153 K
V = 2221.5 (10) Å³	Prism, yellow
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection top

Rigaku Saturn724+ diffractometer	4043 independent reflections
Radiation source: fine-focus sealed tube	3601 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 25.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −11→9
T_min = 0.728, T_max = 1.000	k = −12→11
10036 measured reflections	l = −19→28

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0344P)² + 0.2887P] where P = (F_o² + 2F_c²)/3
4043 reflections	(Δ/σ)_max = 0.002
263 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₄H₂₂Br₂N₂S	V = 2221.5 (10) Å³
M_r = 530.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5636 (19) Å	µ = 3.76 mm⁻¹
b = 10.630 (2) Å	T = 153 K
c = 23.708 (6) Å	0.24 × 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)
T_min = 0.728, T_max = 1.000	R_int = 0.022
10036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.04	Δρ_max = 0.68 e Å⁻³
4043 reflections	Δρ_min = −0.38 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Br1	0.45970 (3)	−0.41644 (2)	1.234842 (12)	0.03454 (9)
Br2	1.07815 (3)	0.96352 (2)	0.907769 (15)	0.04347 (11)
C1	0.3098 (3)	0.3035 (2)	0.92713 (11)	0.0229 (5)
C2	0.5517 (3)	0.3754 (2)	0.96667 (11)	0.0217 (5)
C3	0.5857 (3)	0.2828 (2)	1.01093 (11)	0.0249 (5)
H3	0.6838	0.2748	1.0403	0.030*
C4	0.4721 (3)	0.2021 (2)	1.01114 (11)	0.0224 (5)
C5	0.5015 (3)	0.1044 (2)	1.05768 (11)	0.0250 (5)
H5	0.6018	0.0889	1.0834	0.030*
C6	0.3944 (3)	0.0364 (2)	1.06569 (11)	0.0237 (5)
H6	0.2947	0.0559	1.0407	0.028*
C7	0.4157 (3)	−0.0662 (2)	1.10957 (11)	0.0224 (5)
C8	0.2879 (3)	−0.1289 (2)	1.10968 (11)	0.0264 (5)
H8	0.1922	−0.1009	1.0840	0.032*
C9	0.2998 (3)	−0.2319 (2)	1.14709 (11)	0.0281 (6)
H9	0.2135	−0.2736	1.1462	0.034*
C10	0.4420 (3)	−0.2715 (2)	1.18561 (11)	0.0249 (5)
C11	0.5712 (3)	−0.2086 (2)	1.18849 (11)	0.0264 (5)
H11	0.6663	−0.2346	1.2157	0.032*
C12	0.5576 (3)	−0.1069 (2)	1.15050 (11)	0.0249 (5)
H12	0.6444	−0.0648	1.1522	0.030*
C13	0.6671 (3)	0.4638 (2)	0.96501 (11)	0.0235 (5)
H13	0.7624	0.4602	0.9967	0.028*
C14	0.6451 (3)	0.5488 (2)	0.92140 (11)	0.0239 (5)
H14	0.5499	0.5494	0.8896	0.029*
C15	0.7548 (3)	0.6417 (2)	0.91800 (11)	0.0232 (5)
C16	0.7173 (3)	0.7171 (2)	0.86599 (11)	0.0262 (5)
H16	0.6253	0.7041	0.8333	0.031*
C17	0.8135 (3)	0.8107 (2)	0.86184 (12)	0.0289 (6)
H17	0.7866	0.8603	0.8269	0.035*
C18	0.9497 (3)	0.8291 (2)	0.91031 (12)	0.0271 (6)
C19	0.9919 (3)	0.7544 (2)	0.96202 (12)	0.0305 (6)
H19	1.0854	0.7664	0.9940	0.037*
C20	0.8949 (3)	0.6622 (2)	0.96584 (11)	0.0268 (5)
H20	0.9232	0.6127	1.0009	0.032*
C21	0.1228 (3)	0.4306 (2)	0.82034 (13)	0.0367 (7)
H21A	0.2234	0.4381	0.8198	0.044*
H21B	0.0528	0.4108	0.7791	0.044*
C22	0.0793 (4)	0.5525 (3)	0.83894 (15)	0.0501 (8)
H22A	0.1538	0.5757	0.8789	0.060*
H22B	−0.0179	0.5434	0.8425	0.060*
C23	0.0681 (4)	0.6585 (3)	0.79286 (17)	0.0578 (9)
H23A	−0.0001	0.6318	0.7524	0.069*
H23B	0.0241	0.7323	0.8037	0.069*
C24	0.2172 (4)	0.6943 (3)	0.79049 (17)	0.0617 (9)
H24A	0.2892	0.7113	0.8311	0.093*
H24B	0.2043	0.7680	0.7656	0.093*
H24C	0.2535	0.6263	0.7732	0.093*
S1	0.12232 (7)	0.30281 (6)	0.87109 (3)	0.03603 (18)
N1	0.4088 (2)	0.38747 (17)	0.92361 (9)	0.0227 (4)
N2	0.3308 (2)	0.21138 (17)	0.96785 (9)	0.0227 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04852 (18)	0.02501 (14)	0.03030 (16)	−0.00198 (12)	0.01552 (13)	0.00624 (10)
Br2	0.03001 (16)	0.02807 (16)	0.0752 (2)	−0.00696 (12)	0.02359 (15)	0.00722 (13)
C1	0.0247 (12)	0.0208 (12)	0.0245 (13)	0.0002 (11)	0.0111 (10)	−0.0011 (10)
C2	0.0242 (13)	0.0178 (11)	0.0265 (13)	−0.0001 (10)	0.0138 (11)	−0.0024 (10)
C3	0.0227 (12)	0.0242 (12)	0.0271 (14)	0.0013 (11)	0.0089 (10)	0.0017 (10)
C4	0.0270 (13)	0.0185 (11)	0.0255 (13)	0.0015 (11)	0.0143 (11)	−0.0006 (10)
C5	0.0255 (13)	0.0234 (12)	0.0254 (14)	0.0029 (11)	0.0089 (11)	0.0038 (10)
C6	0.0273 (13)	0.0215 (12)	0.0233 (13)	0.0011 (11)	0.0110 (11)	−0.0012 (10)
C7	0.0293 (13)	0.0180 (11)	0.0220 (13)	−0.0006 (10)	0.0122 (11)	−0.0026 (9)
C8	0.0241 (13)	0.0278 (13)	0.0272 (14)	0.0002 (11)	0.0099 (11)	0.0014 (10)
C9	0.0302 (14)	0.0290 (13)	0.0300 (14)	−0.0056 (12)	0.0170 (12)	0.0002 (11)
C10	0.0370 (14)	0.0200 (12)	0.0214 (13)	−0.0017 (11)	0.0153 (11)	−0.0006 (10)
C11	0.0286 (13)	0.0246 (12)	0.0243 (13)	0.0043 (11)	0.0084 (11)	−0.0006 (10)
C12	0.0286 (13)	0.0221 (12)	0.0265 (14)	−0.0037 (11)	0.0134 (11)	−0.0010 (10)
C13	0.0217 (12)	0.0229 (12)	0.0271 (14)	−0.0032 (10)	0.0106 (11)	−0.0029 (10)
C14	0.0241 (12)	0.0237 (12)	0.0248 (13)	−0.0028 (11)	0.0104 (10)	−0.0031 (10)
C15	0.0268 (13)	0.0187 (12)	0.0274 (14)	−0.0029 (10)	0.0141 (11)	−0.0036 (10)
C16	0.0263 (13)	0.0235 (12)	0.0264 (14)	−0.0022 (11)	0.0078 (11)	0.0003 (10)
C17	0.0316 (14)	0.0237 (13)	0.0342 (15)	−0.0009 (11)	0.0159 (12)	0.0048 (10)
C18	0.0251 (13)	0.0185 (12)	0.0429 (16)	−0.0034 (11)	0.0189 (12)	0.0000 (11)
C19	0.0218 (12)	0.0313 (14)	0.0358 (16)	−0.0043 (12)	0.0084 (11)	−0.0048 (11)
C20	0.0265 (13)	0.0268 (13)	0.0261 (14)	−0.0011 (11)	0.0092 (11)	0.0031 (10)
C21	0.0338 (15)	0.0372 (15)	0.0325 (16)	−0.0050 (13)	0.0055 (12)	0.0049 (12)
C22	0.061 (2)	0.0488 (18)	0.054 (2)	0.0073 (16)	0.0371 (17)	0.0083 (15)
C23	0.073 (2)	0.0448 (18)	0.067 (2)	0.0212 (17)	0.0398 (19)	0.0228 (17)
C24	0.075 (2)	0.0504 (19)	0.073 (3)	0.0016 (18)	0.043 (2)	0.0210 (17)
S1	0.0271 (3)	0.0365 (4)	0.0372 (4)	−0.0085 (3)	0.0044 (3)	0.0112 (3)
N1	0.0244 (11)	0.0200 (10)	0.0244 (11)	−0.0030 (9)	0.0103 (9)	0.0004 (8)
N2	0.0252 (11)	0.0202 (10)	0.0244 (11)	−0.0023 (8)	0.0114 (9)	0.0020 (8)

Geometric parameters (Å, º) top

Br1—C10	1.901 (2)	C13—H13	0.9300
Br2—C18	1.901 (2)	C14—C15	1.466 (3)
C1—N1	1.328 (3)	C14—H14	0.9300
C1—N2	1.334 (3)	C15—C16	1.395 (3)
C1—S1	1.770 (2)	C15—C20	1.397 (3)
C2—N1	1.358 (3)	C16—C17	1.385 (3)
C2—C3	1.382 (3)	C16—H16	0.9300
C2—C13	1.462 (3)	C17—C18	1.376 (3)
C3—C4	1.386 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.383 (3)
C4—N2	1.347 (3)	C19—C20	1.376 (3)
C4—C5	1.461 (3)	C19—H19	0.9300
C5—C6	1.326 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.479 (4)
C6—C7	1.466 (3)	C21—S1	1.816 (3)
C6—H6	0.9300	C21—H21A	0.9700
C7—C8	1.393 (3)	C21—H21B	0.9700
C7—C12	1.396 (3)	C22—C23	1.544 (4)
C8—C9	1.386 (3)	C22—H22A	0.9700
C8—H8	0.9300	C22—H22B	0.9700
C9—C10	1.377 (3)	C23—C24	1.497 (4)
C9—H9	0.9300	C23—H23A	0.9700
C10—C11	1.383 (3)	C23—H23B	0.9700
C11—C12	1.381 (3)	C24—H24A	0.9600
C11—H11	0.9300	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.327 (3)

N1—C1—N2	128.9 (2)	C20—C15—C14	122.8 (2)
N1—C1—S1	119.68 (17)	C17—C16—C15	121.7 (2)
N2—C1—S1	111.38 (17)	C17—C16—H16	119.2
N1—C2—C3	120.7 (2)	C15—C16—H16	119.2
N1—C2—C13	118.0 (2)	C18—C17—C16	118.9 (2)
C3—C2—C13	121.3 (2)	C18—C17—H17	120.6
C2—C3—C4	119.3 (2)	C16—C17—H17	120.6
C2—C3—H3	120.3	C17—C18—C19	121.0 (2)
C4—C3—H3	120.3	C17—C18—Br2	119.62 (19)
N2—C4—C3	120.6 (2)	C19—C18—Br2	119.33 (19)
N2—C4—C5	118.0 (2)	C20—C19—C18	119.6 (2)
C3—C4—C5	121.4 (2)	C20—C19—H19	120.2
C6—C5—C4	124.3 (2)	C18—C19—H19	120.2
C6—C5—H5	117.9	C19—C20—C15	121.1 (2)
C4—C5—H5	117.9	C19—C20—H20	119.4
C5—C6—C7	127.2 (2)	C15—C20—H20	119.4
C5—C6—H6	116.4	C22—C21—S1	112.6 (2)
C7—C6—H6	116.4	C22—C21—H21A	109.1
C8—C7—C12	117.9 (2)	S1—C21—H21A	109.1
C8—C7—C6	118.5 (2)	C22—C21—H21B	109.1
C12—C7—C6	123.7 (2)	S1—C21—H21B	109.1
C9—C8—C7	121.6 (2)	H21A—C21—H21B	107.8
C9—C8—H8	119.2	C21—C22—C23	112.3 (3)
C7—C8—H8	119.2	C21—C22—H22A	109.2
C10—C9—C8	118.7 (2)	C23—C22—H22A	109.2
C10—C9—H9	120.6	C21—C22—H22B	109.2
C8—C9—H9	120.6	C23—C22—H22B	109.2
C9—C10—C11	121.3 (2)	H22A—C22—H22B	107.9
C9—C10—Br1	118.99 (18)	C24—C23—C22	113.9 (3)
C11—C10—Br1	119.76 (18)	C24—C23—H23A	108.8
C12—C11—C10	119.3 (2)	C22—C23—H23A	108.8
C12—C11—H11	120.3	C24—C23—H23B	108.8
C10—C11—H11	120.3	C22—C23—H23B	108.8
C11—C12—C7	121.1 (2)	H23A—C23—H23B	107.7
C11—C12—H12	119.5	C23—C24—H24A	109.5
C7—C12—H12	119.5	C23—C24—H24B	109.5
C14—C13—C2	124.4 (2)	H24A—C24—H24B	109.5
C14—C13—H13	117.8	C23—C24—H24C	109.5
C2—C13—H13	117.8	H24A—C24—H24C	109.5
C13—C14—C15	127.0 (2)	H24B—C24—H24C	109.5
C13—C14—H14	116.5	C1—S1—C21	103.43 (12)
C15—C14—H14	116.5	C1—N1—C2	115.05 (19)
C16—C15—C20	117.7 (2)	C1—N2—C4	115.4 (2)
C16—C15—C14	119.4 (2)

N1—C2—C3—C4	−0.1 (3)	C20—C15—C16—C17	−1.1 (4)
C13—C2—C3—C4	179.2 (2)	C14—C15—C16—C17	176.6 (2)
C2—C3—C4—N2	1.6 (3)	C15—C16—C17—C18	0.2 (4)
C2—C3—C4—C5	−178.7 (2)	C16—C17—C18—C19	1.2 (4)
N2—C4—C5—C6	−10.4 (3)	C16—C17—C18—Br2	−176.17 (18)
C3—C4—C5—C6	170.0 (2)	C17—C18—C19—C20	−1.6 (4)
C4—C5—C6—C7	177.3 (2)	Br2—C18—C19—C20	175.71 (18)
C5—C6—C7—C8	−178.2 (2)	C18—C19—C20—C15	0.7 (4)
C5—C6—C7—C12	0.3 (4)	C16—C15—C20—C19	0.6 (4)
C12—C7—C8—C9	−2.8 (3)	C14—C15—C20—C19	−177.0 (2)
C6—C7—C8—C9	175.8 (2)	S1—C21—C22—C23	−175.6 (2)
C7—C8—C9—C10	1.0 (4)	C21—C22—C23—C24	−67.4 (4)
C8—C9—C10—C11	1.6 (4)	N1—C1—S1—C21	0.2 (2)
C8—C9—C10—Br1	−177.69 (18)	N2—C1—S1—C21	−178.25 (17)
C9—C10—C11—C12	−2.2 (3)	C22—C21—S1—C1	−90.2 (2)
Br1—C10—C11—C12	177.02 (18)	N2—C1—N1—C2	1.8 (3)
C10—C11—C12—C7	0.3 (3)	S1—C1—N1—C2	−176.31 (16)
C8—C7—C12—C11	2.1 (3)	C3—C2—N1—C1	−1.4 (3)
C6—C7—C12—C11	−176.4 (2)	C13—C2—N1—C1	179.2 (2)
N1—C2—C13—C14	−5.7 (3)	N1—C1—N2—C4	−0.4 (3)
C3—C2—C13—C14	174.9 (2)	S1—C1—N2—C4	177.84 (16)
C2—C13—C14—C15	178.4 (2)	C3—C4—N2—C1	−1.4 (3)
C13—C14—C15—C16	174.3 (2)	C5—C4—N2—C1	179.0 (2)
C13—C14—C15—C20	−8.1 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂Br₂N₂S
M_r	530.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	9.5636 (19), 10.630 (2), 23.708 (6)
β (°)	112.82 (3)
V (Å³)	2221.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.76
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.728, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10036, 4043, 3601
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.066, 1.04
No. of reflections	4043
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

Deng, Y., Wang, Y., Cherian, C., Hou, Z., Buck, S. A., Matherly, L. H. & Gangjee, A. (2008). J. Med. Chem. 51, 5052–5063. Web of Science CrossRef PubMed CAS Google Scholar
Joule, J. A. & Mills, K. (2000). Heterocyclic Chemistry, 4th ed. Cambridge: Blackwell Science. Google Scholar
Laar, M. van, Volkerts, E. & Verbaten, M. (2001). Psychopharmacology, 154, 189–197. Web of Science PubMed Google Scholar
Liu, B., Hu, X.., Liu, J., Zhao, Y. & Huang, Z. (2007). Tetrahedron Lett. 48, 5958–5962. Web of Science CrossRef CAS Google Scholar
Nguyen, T. L. (2008). Anticancer Agents Med. Chem. 8, 710–716. CrossRef PubMed CAS Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Walker, S. R., Carter, E. J., Huff, B. C. & Morris, J. C. (2009). Chem. Rev. 109, 3080–3098. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 70| Part 12| December 2014| Page o1282

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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