1,3-Bis[4-(4-pyrid-yl)pyrimidin-2-ylsulfan-yl]propane.

In the title compound, C(21)H(18)N(6)S(2), the dihedral angles between the aromatic rings in the two 4-(4-pyrid-yl)pyrimidine residues are 23.45 (13) and 2.67 (14)°. Whereas one of the C-S-C-C torsion angles corresponds to a staggered conformation, the other is gauche.

Related literature

For related structures, see: Awaleh et al. (2005 ▶); Xie et al. (2005 ▶).

Experimental

Crystal data

C21H18N6S2

M = 418.55

Triclinic,

a = 9.986 (3) Å

b = 10.057 (3) Å

c = 10.645 (3) Å

α = 98.972 (5)°

β = 90.688 (5)°

γ = 112.632 (5)°

V = 971.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 291 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.915, T max = 0.943

5163 measured reflections

3720 independent reflections

2986 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.156

S = 1.02

3720 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010854/bt2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010854/bt2695Isup2.hkl

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

C21H18N6S2	Z = 2
Mr = 418.55	F000 = 436.0
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.986 (3) Å	Cell parameters from 765 reflections
b = 10.057 (3) Å	θ = 2.5–28.0º
c = 10.645 (3) Å	µ = 0.30 mm−1
α = 98.972 (5)º	T = 291 (2) K
β = 90.688 (5)º	Block, yellow
γ = 112.632 (5)º	0.30 × 0.20 × 0.20 mm
V = 971.6 (5) Å3

Bruker CCD area-detector diffractometer	3720 independent reflections
Radiation source: fine-focus sealed tube	2986 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 291(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −12→11
Tmin = 0.915, Tmax = 0.943	k = −12→10
5163 measured reflections	l = −12→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.1031P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3720 reflections	Δρmax = 0.52 e Å−3
262 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.66814 (7)	0.18543 (8)	0.02844 (6)	0.0501 (2)
S2	0.31122 (8)	0.33035 (8)	0.24761 (7)	0.0551 (2)
N1	0.9037 (2)	0.1412 (2)	−0.0039 (2)	0.0484 (5)
N2	0.88209 (19)	0.3272 (2)	−0.10815 (17)	0.0362 (4)
N3	1.1505 (2)	0.6455 (2)	−0.4191 (2)	0.0517 (6)
N4	0.1388 (2)	0.1026 (2)	0.3337 (2)	0.0516 (5)
N5	0.3748 (2)	0.1065 (2)	0.29548 (17)	0.0394 (5)
N6	0.6716 (3)	−0.1928 (3)	0.3320 (2)	0.0558 (6)
C1	0.8365 (2)	0.2254 (3)	−0.0352 (2)	0.0374 (5)
C2	1.0326 (3)	0.1682 (3)	−0.0486 (2)	0.0488 (6)
H2	1.0859	0.1158	−0.0270	0.059*
C3	1.0916 (3)	0.2709 (3)	−0.1260 (2)	0.0449 (6)
H3	1.1826	0.2879	−0.1565	0.054*
C4	1.0107 (2)	0.3474 (2)	−0.1565 (2)	0.0346 (5)
C5	1.0584 (2)	0.4510 (2)	−0.2471 (2)	0.0355 (5)
C6	1.1556 (3)	0.4399 (3)	−0.3360 (2)	0.0438 (6)
H6	1.1925	0.3676	−0.3397	0.053*
C7	1.1961 (3)	0.5387 (3)	−0.4185 (3)	0.0520 (7)
H7	1.2605	0.5294	−0.4784	0.062*
C8	1.0070 (3)	0.5595 (3)	−0.2489 (2)	0.0423 (6)
H8	0.9392	0.5687	−0.1928	0.051*
C9	1.0560 (3)	0.6538 (3)	−0.3333 (3)	0.0504 (6)
H9	1.0216	0.7279	−0.3311	0.061*
C10	0.6054 (3)	0.3160 (3)	−0.0212 (2)	0.0454 (6)
H10A	0.6765	0.4146	0.0080	0.055*
H10B	0.5920	0.2998	−0.1135	0.055*
C11	0.4614 (3)	0.2964 (3)	0.0364 (2)	0.0475 (6)
H11A	0.4109	0.3412	−0.0101	0.057*
H11B	0.4011	0.1928	0.0263	0.057*
C12	0.4802 (3)	0.3627 (3)	0.1758 (2)	0.0446 (6)
H12A	0.5352	0.4674	0.1852	0.054*
H12B	0.5367	0.3228	0.2213	0.054*
C13	0.2733 (3)	0.1608 (3)	0.2964 (2)	0.0416 (5)
C14	0.1092 (3)	−0.0215 (3)	0.3770 (2)	0.0519 (7)
H14	0.0168	−0.0673	0.4037	0.062*
C15	0.2062 (3)	−0.0862 (3)	0.3847 (2)	0.0464 (6)
H15	0.1824	−0.1720	0.4179	0.056*
C16	0.3416 (3)	−0.0181 (2)	0.3409 (2)	0.0373 (5)
C17	0.4557 (3)	−0.0781 (2)	0.3402 (2)	0.0373 (5)
C18	0.4364 (3)	−0.2049 (3)	0.3858 (2)	0.0491 (6)
H18	0.3500	−0.2550	0.4204	0.059*
C19	0.5447 (3)	−0.2568 (3)	0.3800 (2)	0.0546 (7)
H19	0.5286	−0.3423	0.4117	0.066*
C20	0.5885 (3)	−0.0082 (3)	0.2938 (2)	0.0443 (6)
H20	0.6092	0.0798	0.2650	0.053*
C21	0.6903 (3)	−0.0697 (3)	0.2905 (3)	0.0536 (7)
H21	0.7781	−0.0217	0.2569	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.0461 (4)	0.0571 (4)	0.0600 (4)	0.0260 (3)	0.0245 (3)	0.0303 (3)
S2	0.0617 (5)	0.0605 (4)	0.0689 (5)	0.0449 (4)	0.0295 (4)	0.0283 (4)
N1	0.0516 (13)	0.0521 (12)	0.0558 (13)	0.0287 (10)	0.0163 (10)	0.0272 (10)
N2	0.0346 (10)	0.0392 (10)	0.0392 (10)	0.0173 (8)	0.0077 (8)	0.0118 (8)
N3	0.0481 (13)	0.0537 (13)	0.0615 (14)	0.0215 (10)	0.0138 (10)	0.0283 (11)
N4	0.0447 (12)	0.0597 (14)	0.0598 (13)	0.0287 (11)	0.0183 (10)	0.0142 (11)
N5	0.0438 (11)	0.0451 (11)	0.0400 (10)	0.0264 (9)	0.0124 (8)	0.0134 (8)
N6	0.0701 (16)	0.0584 (13)	0.0590 (14)	0.0434 (12)	0.0147 (12)	0.0192 (11)
C1	0.0389 (12)	0.0410 (12)	0.0381 (12)	0.0193 (10)	0.0083 (10)	0.0132 (10)
C2	0.0470 (14)	0.0536 (15)	0.0620 (16)	0.0306 (12)	0.0109 (12)	0.0270 (12)
C3	0.0391 (13)	0.0505 (14)	0.0575 (15)	0.0257 (11)	0.0139 (11)	0.0226 (12)
C4	0.0326 (11)	0.0355 (11)	0.0385 (12)	0.0148 (9)	0.0052 (9)	0.0103 (9)
C5	0.0296 (11)	0.0382 (12)	0.0414 (12)	0.0145 (9)	0.0036 (9)	0.0113 (9)
C6	0.0381 (13)	0.0482 (14)	0.0553 (14)	0.0232 (11)	0.0144 (11)	0.0206 (11)
C7	0.0458 (15)	0.0595 (16)	0.0604 (16)	0.0242 (13)	0.0210 (12)	0.0277 (13)
C8	0.0409 (13)	0.0445 (13)	0.0485 (13)	0.0219 (11)	0.0099 (10)	0.0139 (11)
C9	0.0516 (15)	0.0439 (14)	0.0654 (16)	0.0244 (12)	0.0104 (13)	0.0218 (12)
C10	0.0450 (14)	0.0548 (15)	0.0446 (13)	0.0251 (12)	0.0125 (11)	0.0164 (11)
C11	0.0392 (13)	0.0628 (16)	0.0494 (14)	0.0265 (12)	0.0092 (11)	0.0172 (12)
C12	0.0447 (14)	0.0477 (13)	0.0508 (14)	0.0251 (11)	0.0122 (11)	0.0160 (11)
C13	0.0477 (14)	0.0485 (13)	0.0392 (12)	0.0294 (11)	0.0123 (10)	0.0097 (10)
C14	0.0455 (15)	0.0552 (15)	0.0556 (15)	0.0197 (12)	0.0189 (12)	0.0098 (12)
C15	0.0501 (15)	0.0438 (13)	0.0455 (14)	0.0172 (12)	0.0153 (11)	0.0109 (11)
C16	0.0441 (13)	0.0399 (12)	0.0309 (11)	0.0200 (10)	0.0073 (9)	0.0057 (9)
C17	0.0488 (14)	0.0389 (12)	0.0299 (11)	0.0226 (10)	0.0091 (9)	0.0077 (9)
C18	0.0627 (16)	0.0483 (14)	0.0488 (14)	0.0303 (13)	0.0199 (12)	0.0201 (11)
C19	0.080 (2)	0.0489 (15)	0.0537 (15)	0.0400 (14)	0.0211 (14)	0.0233 (12)
C20	0.0506 (15)	0.0425 (13)	0.0508 (14)	0.0256 (11)	0.0134 (11)	0.0193 (11)
C21	0.0560 (16)	0.0590 (16)	0.0627 (16)	0.0353 (14)	0.0207 (13)	0.0242 (13)

S1—C1	1.743 (2)	C7—H7	0.9300
S1—C10	1.799 (3)	C8—C9	1.365 (3)
S2—C13	1.762 (3)	C8—H8	0.9300
S2—C12	1.796 (2)	C9—H9	0.9300
N1—C2	1.320 (3)	C10—C11	1.525 (3)
N1—C1	1.342 (3)	C10—H10A	0.9700
N2—C1	1.325 (3)	C10—H10B	0.9700
N2—C4	1.343 (3)	C11—C12	1.507 (3)
N3—C7	1.320 (3)	C11—H11A	0.9700
N3—C9	1.338 (3)	C11—H11B	0.9700
N4—C14	1.325 (3)	C12—H12A	0.9700
N4—C13	1.336 (3)	C12—H12B	0.9700
N5—C13	1.323 (3)	C14—C15	1.367 (4)
N5—C16	1.337 (3)	C14—H14	0.9300
N6—C21	1.326 (3)	C15—C16	1.385 (3)
N6—C19	1.330 (4)	C15—H15	0.9300
C2—C3	1.379 (3)	C16—C17	1.480 (3)
C2—H2	0.9300	C17—C18	1.381 (3)
C3—C4	1.379 (3)	C17—C20	1.380 (3)
C3—H3	0.9300	C18—C19	1.368 (4)
C4—C5	1.478 (3)	C18—H18	0.9300
C5—C8	1.376 (3)	C19—H19	0.9300
C5—C6	1.386 (3)	C20—C21	1.377 (4)
C6—C7	1.376 (3)	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C1—S1—C10	103.68 (11)	H10A—C10—H10B	108.4
C13—S2—C12	102.41 (11)	C12—C11—C10	113.0 (2)
C2—N1—C1	114.9 (2)	C12—C11—H11A	109.0
C1—N2—C4	115.73 (19)	C10—C11—H11A	109.0
C7—N3—C9	115.9 (2)	C12—C11—H11B	109.0
C14—N4—C13	114.3 (2)	C10—C11—H11B	109.0
C13—N5—C16	116.7 (2)	H11A—C11—H11B	107.8
C21—N6—C19	115.5 (2)	C11—C12—S2	113.52 (17)
N2—C1—N1	127.7 (2)	C11—C12—H12A	108.9
N2—C1—S1	119.77 (17)	S2—C12—H12A	108.9
N1—C1—S1	112.50 (17)	C11—C12—H12B	108.9
N1—C2—C3	122.8 (2)	S2—C12—H12B	108.9
N1—C2—H2	118.6	H12A—C12—H12B	107.7
C3—C2—H2	118.6	N5—C13—N4	127.3 (2)
C4—C3—C2	117.5 (2)	N5—C13—S2	119.94 (18)
C4—C3—H3	121.2	N4—C13—S2	112.72 (18)
C2—C3—H3	121.2	N4—C14—C15	124.0 (2)
N2—C4—C3	121.2 (2)	N4—C14—H14	118.0
N2—C4—C5	116.95 (19)	C15—C14—H14	118.0
C3—C4—C5	121.8 (2)	C14—C15—C16	116.9 (2)
C8—C5—C6	117.4 (2)	C14—C15—H15	121.6
C8—C5—C4	122.0 (2)	C16—C15—H15	121.6
C6—C5—C4	120.6 (2)	N5—C16—C15	120.7 (2)
C7—C6—C5	118.4 (2)	N5—C16—C17	116.6 (2)
C7—C6—H6	120.8	C15—C16—C17	122.7 (2)
C5—C6—H6	120.8	C18—C17—C20	116.4 (2)
N3—C7—C6	124.9 (2)	C18—C17—C16	122.6 (2)
N3—C7—H7	117.6	C20—C17—C16	121.0 (2)
C6—C7—H7	117.6	C19—C18—C17	119.9 (2)
C9—C8—C5	119.8 (2)	C19—C18—H18	120.1
C9—C8—H8	120.1	C17—C18—H18	120.1
C5—C8—H8	120.1	N6—C19—C18	124.3 (2)
N3—C9—C8	123.7 (2)	N6—C19—H19	117.8
N3—C9—H9	118.1	C18—C19—H19	117.8
C8—C9—H9	118.1	C21—C20—C17	119.5 (2)
C11—C10—S1	108.09 (17)	C21—C20—H20	120.3
C11—C10—H10A	110.1	C17—C20—H20	120.3
S1—C10—H10A	110.1	N6—C21—C20	124.4 (2)
C11—C10—H10B	110.1	N6—C21—H21	117.8
S1—C10—H10B	110.1	C20—C21—H21	117.8