1,2-Bis[4-(2-pyrid­yl)pyrimidin-2-ylsulfan­yl]ethane

The title compound, C₂₀H₁₆N₆S₂, was obtained by the reaction of 1,2-dibromo­ethane and the potassium salt of 4-(2-pyrid­yl)pyrimidine-2-thione in EtOH. The mol­ecule has an inversion centre, with the two 4-(2-pyrid­yl)pyrimidin-2-yl fragments parallel.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.205
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C5      ..       7.53 su
PLAT410_ALERT_2_B Short Intra H...H Contact  H4     ..  H7      ..       1.87 Ang.
PLAT411_ALERT_2_B Short Inter H...H Contact  H1     ..  H4      ..       1.99 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C1      ..       5.72 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.25 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       6.44 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

1,2-Bis[4-(2-pyridyl)pyrimidin-2-ylsulfanyl]ethane

Crystal data

C20H16N6S2	F(000) = 420
Mr = 404.53	Dx = 1.431 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2282 reflections
a = 9.307 (2) Å	θ = 2.8–26.3°
b = 11.672 (3) Å	µ = 0.30 mm^−1
c = 8.7531 (19) Å	T = 294 K
β = 99.221 (4)°	Block, yellow
V = 938.5 (4) Å^3	0.24 × 0.22 × 0.16 mm
Z = 2

Data collection

Bruker APEX-II CCD area-detector diffractometer	1706 independent reflections
Radiation source: fine-focus sealed tube	1337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.931, Tmax = 0.953	k = −12→14
4756 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.205	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1197P)^2 + 0.8118P] where P = (Fo^2 + 2Fc^2)/3
1706 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.62 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
C1	0.5623 (4)	0.9047 (3)	0.8120 (4)	0.0516 (9)
H1	0.5819	0.9820	0.8000	0.062*
C2	0.6499 (4)	0.8223 (3)	0.7634 (4)	0.0519 (9)
H2	0.7301	0.8425	0.7180	0.062*
C3	0.6164 (4)	0.7096 (3)	0.7835 (5)	0.0575 (10)
H3	0.6752	0.6538	0.7494	0.069*
C4	0.5046 (3)	0.6759 (3)	0.8490 (4)	0.0411 (8)
H4	0.4855	0.5985	0.8613	0.049*
C5	0.4210 (3)	0.7558 (3)	0.8963 (3)	0.0380 (7)
C6	0.2962 (3)	0.7129 (3)	0.9700 (3)	0.0382 (7)
C7	0.2765 (4)	0.5977 (3)	0.9950 (4)	0.0483 (8)
H7	0.3405	0.5430	0.9677	0.058*
C8	0.1589 (4)	0.5673 (3)	1.0615 (4)	0.0532 (9)
H8	0.1431	0.4899	1.0780	0.064*
C9	0.0958 (3)	0.7516 (3)	1.0766 (4)	0.0434 (8)
C10	0.0307 (4)	0.9860 (3)	1.0830 (4)	0.0489 (9)
H10A	0.0006	1.0446	1.1498	0.059*
H10B	0.1361	0.9871	1.0956	0.059*
N1	0.4439 (4)	0.8709 (3)	0.8794 (4)	0.0614 (9)
N2	0.2051 (3)	0.7925 (2)	1.0118 (3)	0.0396 (7)
N3	0.0659 (3)	0.6433 (3)	1.1039 (4)	0.0498 (7)
S1	−0.02789 (10)	0.84806 (9)	1.14217 (11)	0.0570 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0487 (19)	0.0462 (19)	0.064 (2)	−0.0044 (16)	0.0206 (16)	0.0032 (17)
C2	0.0402 (18)	0.059 (2)	0.060 (2)	−0.0060 (16)	0.0166 (15)	−0.0003 (17)
C3	0.047 (2)	0.051 (2)	0.079 (3)	0.0052 (16)	0.0215 (18)	−0.0062 (18)
C4	0.0374 (16)	0.0294 (15)	0.060 (2)	0.0011 (12)	0.0188 (14)	−0.0044 (13)
C5	0.0384 (16)	0.0360 (16)	0.0389 (15)	−0.0035 (13)	0.0038 (12)	−0.0001 (13)
C6	0.0372 (16)	0.0379 (17)	0.0388 (16)	−0.0026 (13)	0.0041 (13)	−0.0014 (13)
C7	0.0479 (19)	0.0408 (18)	0.057 (2)	0.0000 (15)	0.0109 (16)	0.0008 (15)
C8	0.054 (2)	0.0410 (19)	0.063 (2)	−0.0105 (16)	0.0063 (17)	0.0081 (16)
C9	0.0391 (17)	0.0508 (19)	0.0405 (16)	−0.0070 (15)	0.0073 (13)	−0.0016 (14)
C10	0.0431 (18)	0.0497 (19)	0.0570 (19)	−0.0020 (15)	0.0178 (15)	−0.0149 (16)
N1	0.063 (2)	0.056 (2)	0.067 (2)	−0.0029 (15)	0.0175 (16)	0.0044 (15)
N2	0.0372 (14)	0.0414 (15)	0.0421 (14)	−0.0032 (11)	0.0122 (11)	−0.0010 (11)
N3	0.0475 (16)	0.0478 (17)	0.0556 (17)	−0.0094 (13)	0.0126 (13)	0.0064 (13)
S1	0.0473 (6)	0.0627 (7)	0.0682 (7)	−0.0023 (4)	0.0310 (5)	−0.0015 (4)

Geometric parameters (Å, º)

C1—C2	1.372 (5)	C6—C7	1.379 (5)
C1—N1	1.387 (5)	C7—C8	1.366 (5)
C1—H1	0.9300	C7—H7	0.9300
C2—C3	1.370 (5)	C8—N3	1.333 (5)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.326 (5)	C9—N3	1.325 (5)
C3—H3	0.9300	C9—N2	1.330 (4)
C4—C5	1.323 (4)	C9—S1	1.770 (4)
C4—H4	0.9300	C10—C10^i	1.509 (7)
C5—N1	1.373 (5)	C10—S1	1.802 (4)
C5—C6	1.502 (4)	C10—H10A	0.9700
C6—N2	1.347 (4)	C10—H10B	0.9700
C2—C1—N1	119.0 (3)	C8—C7—H7	121.4
C2—C1—H1	120.5	C6—C7—H7	121.4
N1—C1—H1	120.5	N3—C8—C7	123.1 (3)
C3—C2—C1	118.3 (3)	N3—C8—H8	118.4
C3—C2—H2	120.8	C7—C8—H8	118.4
C1—C2—H2	120.8	N3—C9—N2	128.1 (3)
C4—C3—C2	123.5 (3)	N3—C9—S1	112.5 (2)
C4—C3—H3	118.3	N2—C9—S1	119.5 (3)
C2—C3—H3	118.3	C10^i—C10—S1	112.6 (3)
C5—C4—C3	117.9 (3)	C10^i—C10—H10A	109.1
C5—C4—H4	121.1	S1—C10—H10A	109.1
C3—C4—H4	121.1	C10^i—C10—H10B	109.1
C4—C5—N1	123.2 (3)	S1—C10—H10B	109.1
C4—C5—C6	115.7 (3)	H10A—C10—H10B	107.8
N1—C5—C6	121.1 (3)	C5—N1—C1	118.2 (3)
N2—C6—C7	121.6 (3)	C9—N2—C6	115.2 (3)
N2—C6—C5	116.8 (3)	C9—N3—C8	114.8 (3)
C7—C6—C5	121.6 (3)	C9—S1—C10	103.45 (16)
C8—C7—C6	117.2 (3)
N1—C1—C2—C3	0.1 (6)	C6—C5—N1—C1	179.2 (3)
C1—C2—C3—C4	−0.8 (6)	C2—C1—N1—C5	0.9 (5)
C2—C3—C4—C5	0.4 (6)	N3—C9—N2—C6	−0.4 (5)
C3—C4—C5—N1	0.7 (5)	S1—C9—N2—C6	178.0 (2)
C3—C4—C5—C6	−179.8 (3)	C7—C6—N2—C9	−0.6 (4)
C4—C5—C6—N2	−176.6 (3)	C5—C6—N2—C9	180.0 (2)
N1—C5—C6—N2	2.9 (4)	N2—C9—N3—C8	0.7 (5)
C4—C5—C6—C7	3.9 (4)	S1—C9—N3—C8	−177.8 (2)
N1—C5—C6—C7	−176.6 (3)	C7—C8—N3—C9	0.0 (5)
N2—C6—C7—C8	1.2 (5)	N3—C9—S1—C10	−177.2 (2)
C5—C6—C7—C8	−179.4 (3)	N2—C9—S1—C10	4.2 (3)
C6—C7—C8—N3	−0.9 (5)	C10^i—C10—S1—C9	83.7 (3)
C4—C5—N1—C1	−1.3 (5)

Symmetry code: (i) −x, −y+2, −z+2.