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

Abstract

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.

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 ▸).

Experimental  

Crystal data  

• C₂₄H₂₄N₂S

• M _r = 372.51

• Monoclinic,

• a = 9.0447 (18) Å

• b = 9.3798 (19) Å

• c = 23.802 (7) Å

• β = 103.44 (3)°

• V = 1964.0 (8) ų

• Z = 4

• Mo Kα radiation

• μ = 0.18 mm⁻¹

• T = 153 K

• 0.26 × 0.23 × 0.22 mm

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

Refinement  

• R[F ² > 2σ(F ²)] = 0.034

• wR(F ²) = 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.

Supplementary Material

CCDC reference: 1010472

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

supplementary crystallographic information

Figures

Fig. 1.

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

Fig. 2.

Packing diagram for (I).

Crystal data

C24H24N2S	F(000) = 792
Mr = 372.51	Dx = 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

Rigaku CCD diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 25.2°, θmin = 3.9°
Absorption correction: multi-scan multi-scan	h = −10→8
Tmin = 0.830, Tmax = 1.000	k = −10→11
9602 measured reflections	l = −28→28

Refinement

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(Fo2) + (0.0468P)2 + 0.4259P] where P = (Fo2 + 2Fc2)/3
3487 reflections	(Δ/σ)max = 0.002
245 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)