2-Benzyl-sulfanyl-4-pentyl-6-(phenyl-sulfan-yl)pyrimidine-5-carbonitrile.

In the title pyrimidine derivative, C(23)H(23)N(3)S(2), the phenyl-sulfanyl and benzyl-sulfanyl benzene rings are orientated away from the carbonitrile group and are twisted out of the plane of the central ring with dihedral angles of 77.66 (6) and 64.73 (5)°, respectively. The n-pentyl group has an extended trans conformation. In the crystal, supra-molecular layers in the ab plane are sustained by C-H⋯π and π-π inter-actions [pyrimidine-phenyl-sulfanyl centroid-centroid distance = 3.8087 (7) Å].

Related literature

For the chemotherapeutic activity of pyrimidine derivatives, see: Al-Safarjalani et al. (2005 ▶); Pauwels (2004 ▶); Hawser et al. (2006 ▶), Al-Omar et al. (2010 ▶); Al-Abdullah et al. (2011 ▶). For a related pyrimidine structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C23H23N3S2

M = 405.56

Monoclinic,

a = 9.0093 (1) Å

b = 8.2137 (1) Å

c = 28.6398 (3) Å

β = 98.427 (1)°

V = 2096.45 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.39 mm−1

T = 100 K

0.25 × 0.25 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO: Agilent, 2010 ▶) T min = 0.586, T max = 0.715

8836 measured reflections

4307 independent reflections

4029 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.02

4307 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044746/hg5126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044746/hg5126Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044746/hg5126Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H23N3S2	F(000) = 856
Mr = 405.56	Dx = 1.285 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 5846 reflections
a = 9.0093 (1) Å	θ = 3.1–76.4°
b = 8.2137 (1) Å	µ = 2.39 mm−1
c = 28.6398 (3) Å	T = 100 K
β = 98.427 (1)°	Block, colourless
V = 2096.45 (4) Å3	0.25 × 0.25 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4307 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4029 reflections with I > 2σ(I)
Mirror	Rint = 0.017
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 5.0°
ω scan	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO: Agilent, 2010)	k = −10→10
Tmin = 0.586, Tmax = 0.715	l = −35→33
8836 measured reflections

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) = 0.084	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.5251P] where P = (Fo2 + 2Fc2)/3
4307 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.30604 (3)	0.80793 (4)	0.220499 (10)	0.02127 (9)
S2	0.67551 (3)	0.34287 (4)	0.296075 (10)	0.02388 (9)
N1	0.40792 (11)	0.79888 (13)	0.31052 (3)	0.0209 (2)
N2	0.48869 (10)	0.58292 (12)	0.26357 (3)	0.0190 (2)
N3	0.73908 (13)	0.46797 (16)	0.41882 (4)	0.0307 (3)
C1	0.41211 (12)	0.71875 (14)	0.26995 (4)	0.0182 (2)
C2	0.56944 (12)	0.52008 (14)	0.30172 (4)	0.0189 (2)
C3	0.57250 (12)	0.59182 (15)	0.34636 (4)	0.0196 (2)
C4	0.48934 (12)	0.73471 (15)	0.34910 (4)	0.0203 (2)
C5	0.33729 (16)	0.66417 (16)	0.17420 (4)	0.0272 (3)
H5A	0.4438	0.6301	0.1787	0.033*
H5B	0.2746	0.5660	0.1760	0.033*
C6	0.29747 (14)	0.74341 (15)	0.12657 (4)	0.0217 (2)
C7	0.14885 (14)	0.77277 (16)	0.10733 (4)	0.0244 (3)
H7	0.0705	0.7464	0.1249	0.029*
C8	0.11432 (16)	0.84024 (17)	0.06264 (5)	0.0292 (3)
H8	0.0126	0.8595	0.0498	0.035*
C9	0.22769 (17)	0.87966 (17)	0.03667 (5)	0.0325 (3)
H9	0.2038	0.9244	0.0059	0.039*
C10	0.37576 (17)	0.85339 (18)	0.05583 (5)	0.0335 (3)
H10	0.4538	0.8814	0.0383	0.040*
C11	0.41074 (14)	0.78623 (17)	0.10058 (5)	0.0283 (3)
H11	0.5128	0.7693	0.1136	0.034*
C12	0.63604 (13)	0.31303 (15)	0.23406 (4)	0.0215 (2)
C13	0.70954 (14)	0.40745 (16)	0.20428 (5)	0.0261 (3)
H13	0.7836	0.4840	0.2170	0.031*
C14	0.67381 (15)	0.38880 (19)	0.15583 (5)	0.0319 (3)
H14	0.7212	0.4550	0.1352	0.038*
C15	0.56860 (16)	0.2732 (2)	0.13749 (5)	0.0338 (3)
H15	0.5447	0.2600	0.1043	0.041*
C16	0.49858 (15)	0.17724 (18)	0.16746 (5)	0.0320 (3)
H16	0.4283	0.0968	0.1548	0.038*
C17	0.53048 (14)	0.19798 (16)	0.21598 (5)	0.0255 (3)
H17	0.4806	0.1341	0.2366	0.031*
C18	0.66434 (13)	0.52388 (15)	0.38680 (4)	0.0226 (2)
C19	0.48584 (13)	0.82239 (16)	0.39484 (4)	0.0235 (3)
H19A	0.5041	0.9398	0.3903	0.028*
H19B	0.5677	0.7807	0.4187	0.028*
C20	0.33583 (13)	0.80131 (15)	0.41337 (4)	0.0215 (2)
H20A	0.2549	0.8522	0.3910	0.026*
H20B	0.3130	0.6838	0.4153	0.026*
C21	0.33978 (13)	0.87849 (16)	0.46189 (4)	0.0224 (2)
H21A	0.4233	0.8297	0.4837	0.027*
H21B	0.3608	0.9962	0.4595	0.027*
C22	0.19546 (16)	0.85754 (19)	0.48265 (5)	0.0326 (3)
H22A	0.1748	0.7399	0.4856	0.039*
H22B	0.1115	0.9055	0.4608	0.039*
C23	0.20205 (16)	0.93742 (18)	0.53094 (5)	0.0318 (3)
H23A	0.1069	0.9195	0.5429	0.048*
H23B	0.2192	1.0546	0.5281	0.048*
H23C	0.2842	0.8895	0.5528	0.048*

	U11	U22	U33	U12	U13	U23
S1	0.02665 (15)	0.02229 (15)	0.01482 (15)	0.00548 (10)	0.00284 (11)	−0.00166 (10)
S2	0.03252 (17)	0.02058 (15)	0.01754 (15)	0.00567 (11)	0.00031 (11)	−0.00097 (11)
N1	0.0222 (5)	0.0236 (5)	0.0173 (5)	0.0000 (4)	0.0039 (4)	−0.0038 (4)
N2	0.0220 (4)	0.0192 (5)	0.0162 (4)	−0.0009 (4)	0.0037 (4)	−0.0011 (4)
N3	0.0331 (6)	0.0391 (6)	0.0201 (5)	0.0026 (5)	0.0041 (4)	0.0027 (5)
C1	0.0197 (5)	0.0195 (5)	0.0159 (5)	−0.0020 (4)	0.0046 (4)	−0.0009 (4)
C2	0.0200 (5)	0.0189 (5)	0.0181 (5)	−0.0029 (4)	0.0041 (4)	−0.0002 (4)
C3	0.0211 (5)	0.0222 (6)	0.0160 (5)	−0.0025 (4)	0.0040 (4)	0.0000 (4)
C4	0.0202 (5)	0.0248 (6)	0.0164 (5)	−0.0033 (4)	0.0044 (4)	−0.0028 (5)
C5	0.0415 (7)	0.0244 (6)	0.0157 (6)	0.0082 (5)	0.0039 (5)	−0.0031 (5)
C6	0.0300 (6)	0.0202 (5)	0.0151 (5)	0.0030 (5)	0.0040 (4)	−0.0043 (4)
C7	0.0282 (6)	0.0242 (6)	0.0213 (6)	−0.0003 (5)	0.0057 (5)	−0.0051 (5)
C8	0.0350 (7)	0.0303 (7)	0.0202 (6)	0.0068 (5)	−0.0023 (5)	−0.0066 (5)
C9	0.0537 (8)	0.0286 (7)	0.0154 (6)	0.0076 (6)	0.0057 (5)	−0.0008 (5)
C10	0.0432 (7)	0.0352 (7)	0.0257 (7)	0.0001 (6)	0.0171 (6)	−0.0006 (6)
C11	0.0279 (6)	0.0328 (7)	0.0248 (6)	0.0020 (5)	0.0063 (5)	−0.0036 (5)
C12	0.0246 (5)	0.0202 (6)	0.0195 (6)	0.0065 (4)	0.0028 (4)	−0.0019 (4)
C13	0.0272 (6)	0.0258 (6)	0.0263 (6)	0.0048 (5)	0.0068 (5)	−0.0008 (5)
C14	0.0334 (7)	0.0391 (7)	0.0258 (7)	0.0138 (6)	0.0129 (5)	0.0052 (6)
C15	0.0354 (7)	0.0463 (8)	0.0184 (6)	0.0194 (6)	−0.0004 (5)	−0.0049 (6)
C16	0.0304 (6)	0.0337 (7)	0.0288 (7)	0.0072 (5)	−0.0056 (5)	−0.0087 (6)
C17	0.0270 (6)	0.0232 (6)	0.0253 (6)	0.0038 (5)	0.0011 (5)	−0.0009 (5)
C18	0.0254 (5)	0.0260 (6)	0.0174 (5)	−0.0019 (5)	0.0061 (4)	−0.0016 (5)
C19	0.0241 (6)	0.0292 (6)	0.0170 (6)	0.0001 (5)	0.0026 (4)	−0.0062 (5)
C20	0.0264 (6)	0.0231 (6)	0.0153 (5)	−0.0005 (5)	0.0044 (4)	−0.0019 (4)
C21	0.0287 (6)	0.0251 (6)	0.0133 (5)	0.0007 (5)	0.0033 (4)	−0.0005 (5)
C22	0.0375 (7)	0.0385 (8)	0.0241 (7)	−0.0092 (6)	0.0123 (5)	−0.0112 (6)
C23	0.0401 (7)	0.0361 (7)	0.0215 (6)	−0.0031 (6)	0.0125 (5)	−0.0071 (6)

S1—C1	1.7489 (12)	C12—C17	1.3861 (18)
S1—C5	1.8279 (12)	C12—C13	1.3902 (18)
S2—C2	1.7616 (12)	C13—C14	1.3862 (19)
S2—C12	1.7766 (12)	C13—H13	0.9500
N1—C1	1.3408 (15)	C14—C15	1.389 (2)
N1—C4	1.3412 (16)	C14—H14	0.9500
N2—C2	1.3253 (15)	C15—C16	1.384 (2)
N2—C1	1.3383 (15)	C15—H15	0.9500
N3—C18	1.1508 (17)	C16—C17	1.3875 (19)
C2—C3	1.4043 (16)	C16—H16	0.9500
C3—C4	1.4008 (17)	C17—H17	0.9500
C3—C18	1.4342 (16)	C19—C20	1.5324 (16)
C4—C19	1.4993 (16)	C19—H19A	0.9900
C5—C6	1.5066 (16)	C19—H19B	0.9900
C5—H5A	0.9900	C20—C21	1.5229 (16)
C5—H5B	0.9900	C20—H20A	0.9900
C6—C7	1.3923 (17)	C20—H20B	0.9900
C6—C11	1.3935 (17)	C21—C22	1.5167 (17)
C7—C8	1.3875 (18)	C21—H21A	0.9900
C7—H7	0.9500	C21—H21B	0.9900
C8—C9	1.387 (2)	C22—C23	1.5241 (17)
C8—H8	0.9500	C22—H22A	0.9900
C9—C10	1.383 (2)	C22—H22B	0.9900
C9—H9	0.9500	C23—H23A	0.9800
C10—C11	1.3885 (19)	C23—H23B	0.9800
C10—H10	0.9500	C23—H23C	0.9800
C11—H11	0.9500
C1—S1—C5	101.12 (6)	C12—C13—H13	120.3
C2—S2—C12	100.01 (5)	C13—C14—C15	119.97 (13)
C1—N1—C4	116.08 (10)	C13—C14—H14	120.0
C2—N2—C1	116.35 (10)	C15—C14—H14	120.0
N2—C1—N1	127.45 (11)	C16—C15—C14	120.17 (12)
N2—C1—S1	118.03 (8)	C16—C15—H15	119.9
N1—C1—S1	114.51 (9)	C14—C15—H15	119.9
N2—C2—C3	121.48 (11)	C15—C16—C17	120.33 (13)
N2—C2—S2	119.07 (9)	C15—C16—H16	119.8
C3—C2—S2	119.45 (9)	C17—C16—H16	119.8
C4—C3—C2	117.60 (10)	C12—C17—C16	119.20 (13)
C4—C3—C18	122.05 (11)	C12—C17—H17	120.4
C2—C3—C18	120.27 (11)	C16—C17—H17	120.4
N1—C4—C3	121.03 (11)	N3—C18—C3	179.00 (14)
N1—C4—C19	116.87 (11)	C4—C19—C20	112.38 (10)
C3—C4—C19	122.10 (11)	C4—C19—H19A	109.1
C6—C5—S1	109.64 (8)	C20—C19—H19A	109.1
C6—C5—H5A	109.7	C4—C19—H19B	109.1
S1—C5—H5A	109.7	C20—C19—H19B	109.1
C6—C5—H5B	109.7	H19A—C19—H19B	107.9
S1—C5—H5B	109.7	C21—C20—C19	111.41 (10)
H5A—C5—H5B	108.2	C21—C20—H20A	109.3
C7—C6—C11	118.81 (11)	C19—C20—H20A	109.3
C7—C6—C5	121.39 (11)	C21—C20—H20B	109.3
C11—C6—C5	119.79 (11)	C19—C20—H20B	109.3
C8—C7—C6	120.46 (12)	H20A—C20—H20B	108.0
C8—C7—H7	119.8	C22—C21—C20	113.81 (10)
C6—C7—H7	119.8	C22—C21—H21A	108.8
C9—C8—C7	120.31 (12)	C20—C21—H21A	108.8
C9—C8—H8	119.8	C22—C21—H21B	108.8
C7—C8—H8	119.8	C20—C21—H21B	108.8
C10—C9—C8	119.61 (12)	H21A—C21—H21B	107.7
C10—C9—H9	120.2	C21—C22—C23	112.67 (11)
C8—C9—H9	120.2	C21—C22—H22A	109.1
C9—C10—C11	120.23 (12)	C23—C22—H22A	109.1
C9—C10—H10	119.9	C21—C22—H22B	109.1
C11—C10—H10	119.9	C23—C22—H22B	109.1
C10—C11—C6	120.56 (12)	H22A—C22—H22B	107.8
C10—C11—H11	119.7	C22—C23—H23A	109.5
C6—C11—H11	119.7	C22—C23—H23B	109.5
C17—C12—C13	120.91 (12)	H23A—C23—H23B	109.5
C17—C12—S2	119.56 (10)	C22—C23—H23C	109.5
C13—C12—S2	119.52 (10)	H23A—C23—H23C	109.5
C14—C13—C12	119.39 (13)	H23B—C23—H23C	109.5
C14—C13—H13	120.3
C2—N2—C1—N1	0.16 (17)	C11—C6—C7—C8	1.37 (19)
C2—N2—C1—S1	179.08 (8)	C5—C6—C7—C8	−177.55 (11)
C4—N1—C1—N2	−0.37 (18)	C6—C7—C8—C9	−0.2 (2)
C4—N1—C1—S1	−179.33 (8)	C7—C8—C9—C10	−0.9 (2)
C5—S1—C1—N2	2.05 (10)	C8—C9—C10—C11	0.7 (2)
C5—S1—C1—N1	−178.89 (9)	C9—C10—C11—C6	0.5 (2)
C1—N2—C2—C3	0.71 (16)	C7—C6—C11—C10	−1.52 (19)
C1—N2—C2—S2	−179.12 (8)	C5—C6—C11—C10	177.42 (12)
C12—S2—C2—N2	1.98 (10)	C2—S2—C12—C17	−100.77 (10)
C12—S2—C2—C3	−177.85 (9)	C2—S2—C12—C13	78.09 (10)
N2—C2—C3—C4	−1.29 (17)	C17—C12—C13—C14	1.61 (18)
S2—C2—C3—C4	178.54 (8)	S2—C12—C13—C14	−177.23 (9)
N2—C2—C3—C18	−178.17 (10)	C12—C13—C14—C15	−1.89 (19)
S2—C2—C3—C18	1.66 (15)	C13—C14—C15—C16	0.4 (2)
C1—N1—C4—C3	−0.27 (16)	C14—C15—C16—C17	1.4 (2)
C1—N1—C4—C19	−179.88 (10)	C13—C12—C17—C16	0.14 (18)
C2—C3—C4—N1	1.05 (17)	S2—C12—C17—C16	178.98 (10)
C18—C3—C4—N1	177.88 (11)	C15—C16—C17—C12	−1.62 (19)
C2—C3—C4—C19	−179.36 (11)	N1—C4—C19—C20	72.64 (14)
C18—C3—C4—C19	−2.54 (18)	C3—C4—C19—C20	−106.96 (13)
C1—S1—C5—C6	−161.95 (9)	C4—C19—C20—C21	174.92 (10)
S1—C5—C6—C7	−72.54 (14)	C19—C20—C21—C22	−178.46 (11)
S1—C5—C6—C11	108.55 (12)	C20—C21—C22—C23	−179.41 (12)

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21b···Cg1i	0.99	3.00	3.8443 (14)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21b⋯Cg1i	0.99	3.00	3.8443 (14)	148

Symmetry code: (i) .