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

Wang, A.; Li, G.

doi:10.1107/S2056989015008166

organic compounds

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Volume 71| Part 5| May 2015| Page o368

https://doi.org/10.1107/S2056989015008166

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

Aijian Wang ^a ^* and Guanghui Li ^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 22 April 2015; accepted 24 April 2015; online 30 April 2015)

In the title compound, C₂₄H₂₄N₂S, the dihedral angles between the central pyrimidine ring and pendant benzene rings are 18.46 (6) and 5.95 (6)°. The butylsulfanyl side chain adopts a twisted conformation [S—C—C—C = 177.34 (10)° and C—C—C—C = 67.68 (18)°]. No directional interactions beyond typical van der Waals contacts could be identified in the crystal.

Keywords: crystal structure; weak interactions; pyrimidine.

CCDC reference: 1010472

1. Related literature

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009 ); van Laar et al. (2001 ); Casas et al. (2006 ); Deng et al. (2008 ); Nguyen (2008 ). For the synthesis of the title compound, see: Liu et al. (2007 ).

2. Experimental

2.1. Crystal data

C₂₄H₂₄N₂S
M_r = 372.51
Monoclinic, P 2₁ /c
a = 9.0447 (18) Å
b = 9.3798 (19) Å
c = 23.802 (7) Å
β = 103.44 (3)°
V = 1964.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 153 K
0.26 × 0.23 × 0.22 mm

2.2. Data collection

Rigaku Saturn 724+ CCD diffractometer
Absorption correction: multi-scan multi-scan T_min = 0.830, T_max = 1.000
9602 measured reflections
3487 independent reflections
3193 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.087
S = 1.06
3487 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 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: 1010472

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015008166/hb7413sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015008166/hb7413Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015008166/hb7413Isup3.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989015008166/hb7413Isup4.docx

checkCIF report

Related literature top

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009); van Laar et al. (2001); Casas et al. (2006); Deng et al. (2008); Nguyen (2008). For the synthesis of the title compound, see: Liu et al. (2007).

Structure description top

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009); van Laar et al. (2001); Casas et al. (2006); Deng et al. (2008); Nguyen (2008). For the synthesis of the title compound, 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

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids.
	Fig. 2. Packing diagram for (I).

2-Butylsulfanyl-4,6-bis[(E)-styryl]pyrimidine top

Crystal data top

C₂₄H₂₄N₂S	F(000) = 792
M_r = 372.51	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0447 (18) Å	Cell parameters from 4606 reflections
b = 9.3798 (19) Å	θ = 3.9–28.6°
c = 23.802 (7) Å	µ = 0.18 mm⁻¹
β = 103.44 (3)°	T = 153 K
V = 1964.0 (8) Å³	Prism, yellow
Z = 4	0.26 × 0.23 × 0.22 mm

Data collection top

Rigaku CCD diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.2°, θ_min = 3.9°
Absorption correction: multi-scan multi-scan	h = −10→8
T_min = 0.830, T_max = 1.000	k = −10→11
9602 measured reflections	l = −28→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0468P)² + 0.4259P] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max = 0.002
245 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₂₄N₂S	V = 1964.0 (8) Å³
M_r = 372.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0447 (18) Å	µ = 0.18 mm⁻¹
b = 9.3798 (19) Å	T = 153 K
c = 23.802 (7) Å	0.26 × 0.23 × 0.22 mm
β = 103.44 (3)°

Data collection top

Rigaku CCD diffractometer	3487 independent reflections
Absorption correction: multi-scan multi-scan	3193 reflections with I > 2σ(I)
T_min = 0.830, T_max = 1.000	R_int = 0.020
9602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.06	Δρ_max = 0.20 e Å⁻³
3487 reflections	Δρ_min = −0.23 e Å⁻³
245 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
S1	0.14918 (4)	0.26493 (4)	0.884447 (14)	0.02603 (12)
N1	0.29497 (11)	0.49599 (11)	0.93583 (4)	0.0198 (2)
N2	0.14298 (11)	0.35823 (11)	0.98633 (4)	0.0202 (2)
C1	0.20397 (13)	0.38866 (13)	0.94166 (5)	0.0193 (3)
C2	0.17542 (13)	0.45128 (13)	1.03058 (5)	0.0194 (3)
C3	0.26563 (13)	0.57051 (13)	1.02829 (5)	0.0205 (3)
H3	0.2852	0.6377	1.0590	0.025*
C4	0.32650 (13)	0.58934 (13)	0.98031 (5)	0.0191 (3)
C5	0.42814 (13)	0.70891 (13)	0.97653 (5)	0.0204 (3)
H5	0.4634	0.7661	1.0099	0.025*
C6	0.47367 (14)	0.74153 (13)	0.92880 (6)	0.0219 (3)
H6	0.4330	0.6851	0.8957	0.026*
C7	0.57954 (14)	0.85485 (13)	0.92161 (6)	0.0225 (3)
C8	0.60175 (15)	0.88109 (15)	0.86649 (6)	0.0281 (3)
H8	0.5451	0.8285	0.8346	0.034*
C9	0.70538 (16)	0.98295 (16)	0.85754 (7)	0.0343 (4)
H9	0.7194	0.9993	0.8197	0.041*
C10	0.78780 (16)	1.06029 (15)	0.90348 (7)	0.0353 (4)
H10	0.8589	1.1298	0.8974	0.042*
C11	0.76658 (16)	1.03641 (15)	0.95844 (7)	0.0332 (3)
H11	0.8230	1.0901	0.9901	0.040*
C12	0.66348 (15)	0.93468 (14)	0.96766 (6)	0.0273 (3)
H12	0.6498	0.9192	1.0056	0.033*
C13	0.11375 (13)	0.42439 (14)	1.08114 (5)	0.0210 (3)
H13	0.1239	0.4973	1.1095	0.025*
C14	0.04425 (14)	0.30423 (14)	1.08999 (5)	0.0222 (3)
H14	0.0362	0.2324	1.0613	0.027*
C15	−0.02107 (14)	0.27106 (14)	1.13927 (5)	0.0218 (3)
C16	−0.09987 (15)	0.14320 (15)	1.13976 (6)	0.0286 (3)
H16	−0.1076	0.0781	1.1086	0.034*
C17	−0.16687 (16)	0.10953 (16)	1.18474 (7)	0.0341 (3)
H17	−0.2208	0.0224	1.1841	0.041*
C18	−0.15537 (16)	0.20253 (17)	1.23059 (6)	0.0327 (3)
H18	−0.2010	0.1794	1.2616	0.039*
C19	−0.07708 (15)	0.32952 (16)	1.23120 (6)	0.0302 (3)
H19	−0.0692	0.3936	1.2627	0.036*
C20	−0.01020 (15)	0.36359 (15)	1.18626 (6)	0.0265 (3)
H20	0.0438	0.4508	1.1873	0.032*
C21	0.25447 (15)	0.32567 (15)	0.83313 (5)	0.0252 (3)
H21A	0.2058	0.2874	0.7945	0.030*
H21B	0.2489	0.4310	0.8308	0.030*
C22	0.42011 (15)	0.28109 (15)	0.84837 (6)	0.0286 (3)
H22A	0.4260	0.1761	0.8524	0.034*
H22B	0.4702	0.3232	0.8861	0.034*
C23	0.50566 (18)	0.32712 (16)	0.80329 (7)	0.0370 (4)
H23A	0.6071	0.2814	0.8124	0.044*
H23B	0.4501	0.2916	0.7650	0.044*
C24	0.52647 (17)	0.48708 (16)	0.79936 (7)	0.0364 (4)
H24A	0.5838	0.5078	0.7701	0.055*
H24B	0.5823	0.5235	0.8369	0.055*
H24C	0.4267	0.5333	0.7886	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0269 (2)	0.0267 (2)	0.0270 (2)	−0.00895 (13)	0.01143 (15)	−0.00718 (14)
N1	0.0190 (5)	0.0189 (6)	0.0221 (5)	0.0003 (4)	0.0062 (4)	0.0002 (4)
N2	0.0189 (5)	0.0199 (6)	0.0226 (5)	0.0010 (4)	0.0066 (4)	0.0013 (4)
C1	0.0174 (6)	0.0188 (6)	0.0219 (6)	0.0015 (5)	0.0051 (5)	0.0001 (5)
C2	0.0164 (6)	0.0205 (7)	0.0214 (6)	0.0038 (5)	0.0045 (5)	0.0033 (5)
C3	0.0208 (6)	0.0202 (7)	0.0206 (6)	0.0011 (5)	0.0048 (5)	−0.0007 (5)
C4	0.0169 (6)	0.0185 (6)	0.0216 (6)	0.0028 (5)	0.0042 (5)	0.0015 (5)
C5	0.0203 (6)	0.0180 (6)	0.0231 (6)	−0.0003 (5)	0.0052 (5)	−0.0008 (5)
C6	0.0230 (7)	0.0187 (6)	0.0248 (7)	−0.0007 (5)	0.0071 (5)	−0.0010 (5)
C7	0.0218 (6)	0.0184 (6)	0.0292 (7)	0.0026 (5)	0.0096 (5)	0.0023 (5)
C8	0.0299 (7)	0.0268 (7)	0.0299 (7)	0.0007 (6)	0.0116 (6)	0.0030 (6)
C9	0.0355 (8)	0.0322 (8)	0.0410 (9)	0.0035 (6)	0.0207 (7)	0.0129 (7)
C10	0.0260 (7)	0.0243 (8)	0.0595 (10)	−0.0016 (6)	0.0178 (7)	0.0089 (7)
C11	0.0267 (7)	0.0249 (7)	0.0471 (9)	−0.0038 (6)	0.0069 (7)	−0.0020 (7)
C12	0.0270 (7)	0.0235 (7)	0.0327 (7)	−0.0010 (5)	0.0094 (6)	0.0005 (6)
C13	0.0195 (6)	0.0226 (7)	0.0210 (6)	0.0024 (5)	0.0051 (5)	0.0007 (5)
C14	0.0226 (6)	0.0226 (7)	0.0217 (6)	0.0023 (5)	0.0058 (5)	0.0013 (5)
C15	0.0186 (6)	0.0241 (7)	0.0231 (7)	0.0038 (5)	0.0056 (5)	0.0048 (5)
C16	0.0299 (7)	0.0266 (7)	0.0306 (7)	−0.0012 (6)	0.0099 (6)	0.0026 (6)
C17	0.0311 (8)	0.0331 (8)	0.0411 (8)	−0.0036 (6)	0.0148 (7)	0.0108 (7)
C18	0.0291 (8)	0.0413 (9)	0.0324 (8)	0.0077 (6)	0.0171 (6)	0.0142 (7)
C19	0.0322 (7)	0.0361 (8)	0.0240 (7)	0.0080 (6)	0.0102 (6)	0.0040 (6)
C20	0.0277 (7)	0.0271 (7)	0.0261 (7)	0.0008 (6)	0.0092 (6)	0.0043 (6)
C21	0.0269 (7)	0.0296 (7)	0.0195 (6)	−0.0036 (6)	0.0066 (5)	−0.0028 (6)
C22	0.0297 (7)	0.0272 (7)	0.0324 (8)	0.0029 (6)	0.0146 (6)	0.0036 (6)
C23	0.0427 (9)	0.0314 (8)	0.0454 (9)	0.0054 (7)	0.0276 (7)	0.0035 (7)
C24	0.0350 (8)	0.0343 (8)	0.0436 (9)	−0.0003 (6)	0.0171 (7)	0.0063 (7)

Geometric parameters (Å, º) top

S1—C1	1.7701 (13)	C13—H13	0.9500
S1—C21	1.8066 (14)	C14—C15	1.4642 (18)
N1—C1	1.3279 (16)	C14—H14	0.9500
N1—C4	1.3523 (16)	C15—C16	1.3966 (19)
N2—C1	1.3375 (16)	C15—C20	1.4009 (19)
N2—C2	1.3466 (16)	C16—C17	1.384 (2)
C2—C3	1.3929 (18)	C16—H16	0.9500
C2—C13	1.4611 (18)	C17—C18	1.382 (2)
C3—C4	1.3896 (17)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.384 (2)
C4—C5	1.4662 (17)	C18—H18	0.9500
C5—C6	1.3309 (18)	C19—C20	1.3831 (19)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.4670 (18)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.5160 (19)
C7—C8	1.3946 (19)	C21—H21A	0.9900
C7—C12	1.3969 (19)	C21—H21B	0.9900
C8—C9	1.389 (2)	C22—C23	1.5239 (19)
C8—H8	0.9500	C22—H22A	0.9900
C9—C10	1.378 (2)	C22—H22B	0.9900
C9—H9	0.9500	C23—C24	1.518 (2)
C10—C11	1.384 (2)	C23—H23A	0.9900
C10—H10	0.9500	C23—H23B	0.9900
C11—C12	1.3868 (19)	C24—H24A	0.9800
C11—H11	0.9500	C24—H24B	0.9800
C12—H12	0.9500	C24—H24C	0.9800
C13—C14	1.3310 (19)

C1—S1—C21	102.48 (6)	C15—C14—H14	116.6
C1—N1—C4	115.60 (11)	C16—C15—C20	117.82 (12)
C1—N2—C2	115.35 (11)	C16—C15—C14	119.39 (12)
N1—C1—N2	128.69 (12)	C20—C15—C14	122.78 (12)
N1—C1—S1	119.09 (9)	C17—C16—C15	121.23 (13)
N2—C1—S1	112.22 (9)	C17—C16—H16	119.4
N2—C2—C3	120.87 (11)	C15—C16—H16	119.4
N2—C2—C13	118.47 (11)	C18—C17—C16	120.05 (14)
C3—C2—C13	120.66 (12)	C18—C17—H17	120.0
C4—C3—C2	118.80 (12)	C16—C17—H17	120.0
C4—C3—H3	120.6	C17—C18—C19	119.73 (13)
C2—C3—H3	120.6	C17—C18—H18	120.1
N1—C4—C3	120.63 (11)	C19—C18—H18	120.1
N1—C4—C5	117.93 (11)	C20—C19—C18	120.36 (14)
C3—C4—C5	121.43 (12)	C20—C19—H19	119.8
C6—C5—C4	123.44 (12)	C18—C19—H19	119.8
C6—C5—H5	118.3	C19—C20—C15	120.80 (13)
C4—C5—H5	118.3	C19—C20—H20	119.6
C5—C6—C7	127.30 (12)	C15—C20—H20	119.6
C5—C6—H6	116.4	C22—C21—S1	113.46 (9)
C7—C6—H6	116.4	C22—C21—H21A	108.9
C8—C7—C12	118.20 (12)	S1—C21—H21A	108.9
C8—C7—C6	118.57 (12)	C22—C21—H21B	108.9
C12—C7—C6	123.19 (12)	S1—C21—H21B	108.9
C9—C8—C7	121.04 (14)	H21A—C21—H21B	107.7
C9—C8—H8	119.5	C21—C22—C23	112.88 (12)
C7—C8—H8	119.5	C21—C22—H22A	109.0
C10—C9—C8	120.01 (14)	C23—C22—H22A	109.0
C10—C9—H9	120.0	C21—C22—H22B	109.0
C8—C9—H9	120.0	C23—C22—H22B	109.0
C9—C10—C11	119.78 (13)	H22A—C22—H22B	107.8
C9—C10—H10	120.1	C24—C23—C22	114.46 (12)
C11—C10—H10	120.1	C24—C23—H23A	108.6
C10—C11—C12	120.47 (14)	C22—C23—H23A	108.6
C10—C11—H11	119.8	C24—C23—H23B	108.6
C12—C11—H11	119.8	C22—C23—H23B	108.6
C11—C12—C7	120.50 (13)	H23A—C23—H23B	107.6
C11—C12—H12	119.8	C23—C24—H24A	109.5
C7—C12—H12	119.8	C23—C24—H24B	109.5
C14—C13—C2	124.15 (12)	H24A—C24—H24B	109.5
C14—C13—H13	117.9	C23—C24—H24C	109.5
C2—C13—H13	117.9	H24A—C24—H24C	109.5
C13—C14—C15	126.89 (13)	H24B—C24—H24C	109.5
C13—C14—H14	116.6

C4—N1—C1—N2	−2.18 (18)	C8—C9—C10—C11	−0.2 (2)
C4—N1—C1—S1	177.30 (9)	C9—C10—C11—C12	0.3 (2)
C2—N2—C1—N1	1.89 (18)	C10—C11—C12—C7	0.0 (2)
C2—N2—C1—S1	−177.61 (8)	C8—C7—C12—C11	−0.42 (19)
C21—S1—C1—N1	3.44 (11)	C6—C7—C12—C11	177.28 (12)
C21—S1—C1—N2	−177.00 (9)	N2—C2—C13—C14	9.40 (18)
C1—N2—C2—C3	0.51 (16)	C3—C2—C13—C14	−170.62 (12)
C1—N2—C2—C13	−179.51 (10)	C2—C13—C14—C15	−179.42 (11)
N2—C2—C3—C4	−2.32 (17)	C13—C14—C15—C16	175.44 (12)
C13—C2—C3—C4	177.70 (11)	C13—C14—C15—C20	−3.6 (2)
C1—N1—C4—C3	0.06 (16)	C20—C15—C16—C17	0.83 (19)
C1—N1—C4—C5	179.18 (10)	C14—C15—C16—C17	−178.22 (12)
C2—C3—C4—N1	2.01 (17)	C15—C16—C17—C18	−0.6 (2)
C2—C3—C4—C5	−177.07 (11)	C16—C17—C18—C19	0.2 (2)
N1—C4—C5—C6	9.66 (18)	C17—C18—C19—C20	−0.1 (2)
C3—C4—C5—C6	−171.24 (12)	C18—C19—C20—C15	0.4 (2)
C4—C5—C6—C7	−177.30 (11)	C16—C15—C20—C19	−0.72 (18)
C5—C6—C7—C8	−173.89 (12)	C14—C15—C20—C19	178.30 (12)
C5—C6—C7—C12	8.4 (2)	C1—S1—C21—C22	78.82 (11)
C12—C7—C8—C9	0.54 (19)	S1—C21—C22—C23	177.34 (10)
C6—C7—C8—C9	−177.27 (12)	C21—C22—C23—C24	67.68 (18)
C7—C8—C9—C10	−0.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂S
M_r	372.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	9.0447 (18), 9.3798 (19), 23.802 (7)
β (°)	103.44 (3)
V (Å³)	1964.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.26 × 0.23 × 0.22

Data collection
Diffractometer	Rigaku CCD
Absorption correction	Multi-scan multi-scan
T_min, T_max	0.830, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9602, 3487, 3193
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.087, 1.06
No. of reflections	3487
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

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

Acknowledgements

This research was supported financially by the Research Foundation of Jiangsu University (grant No. 13JDG066).

References

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