1,2-Bis(pyrimidin-2-ylsulfan­yl)ethane

The title dithio­ether compound, C₁₀H₁₀N₄S₂, adopts an anti conformation with an intra­molecular S...S non-bonding distance of 4.419 (2) Å. The dihedral angle between the two pyrimidine rings is 6.8 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.088
• wR factor = 0.307
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     -   C5      ..      22.02 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     -   C6      ..      19.68 su

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.307
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.79 mm
PLAT084_ALERT_2_C High R2 Value ..................................       0.31
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.34
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C5     -   C6     ...       1.43 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H10 N4 S2

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

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

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S1. Comment

A large number of complexes of dithioether ligands containing N-heterocyclic groups have been synthesized and investigated, because of their diverse coordination capabilities and the important properties of their metal complexes (Zheng et al., 2003; Hong et al., 2000). However, crystallographic studies of only a few ligands have been reported. In the present paper, we report the crystal structure of the title compound, (I).

As shown in Fig. 1, the molecule adopts an anti conformation (Goodgame et al., 1999) with a pseudo-torsion angle C4—S1···S2—C7 of −174.9 (2)°. The pyrimidine rings (N1/C1–C3/N2/C4 and N3/C7/N4/C8–C10), with a dihedral angle of 6.8 (2)° to each other, incline to the spacer unit plane (S1—C5—C6—S2) at angles of 81.8 (4) and 86.9 (4)°, respectively. The S1···S2 non-bonding distance is 4.419 (2) Å. The bond dimensions are within the range reported in a similar compound, 2,4,6-trimethyl-1,3,5-tris(2-pyrimidinylthiomethyl)benzene (Zheng et al., 2002). Both the S—Csp² and the S—Csp³ bond distances of (I) show little deviation in comparison with those of the analogous compound 1,2-bis(phenylthio)ethane (Hou et al., 2005), despite various substituted groups. The molecule of (I) does not possess any crystallographic symmetry, being different from the inversion symmetry of several reported alkyl dithioether compounds (Chen et al., 2005; Hou et al., 2005).

In the crystal of the binuclear silver(I) nitrate complex with (I) as a chelating and bridging ligand (Zheng et al., 2003), the thioether adopts a gauche conformation with an S···S non-bonding distance of 3.44 (3) Å.

S2. Experimental

Compound (I) was prepared according to the reported procedure (Zheng et al., 2003). Colorless single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a chloroform solution at room temperature.

S3. Refinement

All H atoms were positioned geometrically with Csp²—H = 0.93 Å and Csp³—H = 0.97 Å; they were constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C). The short C5—C6 distance of 1.425 (7) Å may be an artifact of the large atomic displacements.

Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure (Rigaku, 2004).

Figures

Fig. 1. ORTEPII (Johnson, 1976) view of (I), showing atomic displacement ellipsoids at the 30% probability level.

1,2-Bis(pyrimidin-2-ylsulfanyl)ethane

Crystal data

C10H10N4S2	F(000) = 520
Mr = 250.34	Dx = 1.424 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11354 reflections
a = 8.0524 (16) Å	θ = 3.0–27.5°
b = 19.884 (4) Å	µ = 0.43 mm^−1
c = 8.1541 (16) Å	T = 293 K
β = 116.57 (3)°	Needle, colorless
V = 1167.7 (4) Å^3	0.79 × 0.24 × 0.16 mm
Z = 4

Data collection

Rigaku X-AXIS RAPID IP area-detector diffractometer	2663 independent reflections
Radiation source: rotating anode	1706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.725, Tmax = 0.936	k = −25→25
11145 measured reflections	l = −9→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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.307	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.2005P)^2 + 0.4011P] where P = (Fo^2 + 2Fc^2)/3
2663 reflections	(Δ/σ)max = 0.046
145 parameters	Δρmax = 1.17 e Å^−3
0 restraints	Δρmin = −0.94 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	−0.18017 (17)	−0.26723 (5)	−0.1152 (2)	0.0743 (5)
S2	−0.23919 (15)	−0.48544 (6)	−0.2296 (2)	0.0793 (6)
N1	0.0708 (5)	−0.18705 (15)	−0.1171 (5)	0.0537 (8)
N2	0.1370 (5)	−0.30332 (15)	−0.1231 (5)	0.0604 (9)
N3	−0.5083 (5)	−0.56394 (14)	−0.2632 (5)	0.0552 (8)
N4	−0.5653 (5)	−0.44748 (16)	−0.2418 (6)	0.0643 (10)
C1	0.2316 (6)	−0.1727 (2)	−0.1195 (6)	0.0614 (11)
H1B	0.2645	−0.1278	−0.1180	0.074*
C2	0.3493 (6)	−0.2208 (2)	−0.1242 (7)	0.0672 (12)
H2B	0.4601	−0.2097	−0.1271	0.081*
C3	0.2971 (6)	−0.2861 (2)	−0.1245 (7)	0.0685 (12)
H3B	0.3760	−0.3201	−0.1256	0.082*
C4	0.0330 (5)	−0.25188 (18)	−0.1194 (5)	0.0483 (8)
C5	−0.1764 (7)	−0.3603 (3)	−0.0842 (6)	0.0880 (17)
H5A	−0.0516	−0.3755	−0.0041	0.106*
H5B	−0.2578	−0.3732	−0.0307	0.106*
C6	−0.2392 (6)	−0.3889 (3)	−0.2624 (6)	0.0807 (16)
H6A	−0.1566	−0.3767	−0.3150	0.097*
H6B	−0.3632	−0.3731	−0.3431	0.097*
C7	−0.4615 (5)	−0.49969 (17)	−0.2463 (5)	0.0487 (9)
C8	−0.7334 (6)	−0.4635 (2)	−0.2590 (7)	0.0694 (12)
H8A	−0.8103	−0.4292	−0.2556	0.083*
C9	−0.7973 (6)	−0.5280 (2)	−0.2812 (6)	0.0597 (10)
H9A	−0.9161	−0.5380	−0.2964	0.072*
C10	−0.6780 (6)	−0.57709 (19)	−0.2802 (5)	0.0560 (10)
H10A	−0.7167	−0.6217	−0.2917	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0622 (8)	0.0436 (7)	0.1421 (12)	0.0004 (4)	0.0681 (8)	0.0002 (6)
S2	0.0473 (7)	0.0519 (8)	0.1518 (13)	−0.0085 (4)	0.0562 (7)	−0.0281 (7)
N1	0.0515 (18)	0.0385 (16)	0.0745 (19)	−0.0002 (13)	0.0312 (15)	0.0022 (13)
N2	0.0462 (17)	0.0333 (16)	0.105 (2)	−0.0013 (12)	0.0373 (17)	−0.0053 (16)
N3	0.0564 (19)	0.0373 (16)	0.078 (2)	−0.0019 (13)	0.0353 (16)	−0.0062 (14)
N4	0.0490 (18)	0.0357 (16)	0.119 (3)	−0.0031 (13)	0.0475 (19)	−0.0113 (17)
C1	0.054 (2)	0.044 (2)	0.087 (3)	−0.0127 (16)	0.032 (2)	−0.0031 (18)
C2	0.047 (2)	0.066 (3)	0.093 (3)	−0.0176 (19)	0.036 (2)	−0.015 (2)
C3	0.048 (2)	0.050 (2)	0.113 (3)	−0.0006 (17)	0.040 (2)	−0.017 (2)
C4	0.0403 (16)	0.0369 (17)	0.070 (2)	−0.0017 (13)	0.0270 (16)	0.0022 (14)
C5	0.063 (3)	0.133 (5)	0.072 (3)	−0.022 (3)	0.034 (2)	0.004 (3)
C6	0.047 (2)	0.128 (5)	0.070 (2)	−0.013 (3)	0.029 (2)	0.010 (3)
C7	0.0397 (18)	0.0359 (17)	0.074 (2)	−0.0044 (13)	0.0283 (16)	−0.0107 (15)
C8	0.051 (2)	0.050 (2)	0.121 (4)	0.0003 (17)	0.051 (2)	−0.008 (2)
C9	0.047 (2)	0.060 (2)	0.082 (3)	−0.0116 (18)	0.0374 (19)	−0.0066 (19)
C10	0.063 (2)	0.0391 (18)	0.074 (2)	−0.0136 (16)	0.038 (2)	−0.0070 (16)

Geometric parameters (Å, º)

S1—C4	1.759 (4)	C2—C3	1.366 (6)
S1—C5	1.866 (7)	C2—H2B	0.9300
S2—C7	1.757 (4)	C3—H3B	0.9300
S2—C6	1.939 (6)	C5—C6	1.425 (7)
N1—C4	1.323 (5)	C5—H5A	0.9700
N1—C1	1.334 (5)	C5—H5B	0.9700
N2—C4	1.331 (5)	C6—H6A	0.9700
N2—C3	1.338 (5)	C6—H6B	0.9700
N3—C7	1.322 (4)	C8—C9	1.362 (6)
N3—C10	1.337 (5)	C8—H8A	0.9300
N4—C8	1.336 (5)	C9—C10	1.367 (6)
N4—C7	1.344 (5)	C9—H9A	0.9300
C1—C2	1.358 (6)	C10—H10A	0.9300
C1—H1B	0.9300
C4—S1—C5	102.6 (2)	C6—C5—H5B	110.5
C7—S2—C6	102.24 (19)	S1—C5—H5B	110.5
C4—N1—C1	115.2 (3)	H5A—C5—H5B	108.7
C4—N2—C3	115.0 (3)	C5—C6—S2	106.0 (4)
C7—N3—C10	115.5 (3)	C5—C6—H6A	110.5
C8—N4—C7	115.2 (3)	S2—C6—H6A	110.5
N1—C1—C2	123.0 (4)	C5—C6—H6B	110.5
N1—C1—H1B	118.5	S2—C6—H6B	110.5
C2—C1—H1B	118.5	H6A—C6—H6B	108.7
C1—C2—C3	116.8 (4)	N3—C7—N4	126.7 (3)
C1—C2—H2B	121.6	N3—C7—S2	113.4 (3)
C3—C2—H2B	121.6	N4—C7—S2	119.9 (3)
N2—C3—C2	122.7 (4)	N4—C8—C9	122.9 (4)
N2—C3—H3B	118.7	N4—C8—H8A	118.6
C2—C3—H3B	118.7	C9—C8—H8A	118.6
N1—C4—N2	127.3 (4)	C8—C9—C10	116.7 (4)
N1—C4—S1	112.9 (3)	C8—C9—H9A	121.7
N2—C4—S1	119.8 (3)	C10—C9—H9A	121.7
C6—C5—S1	106.3 (4)	N3—C10—C9	122.9 (3)
C6—C5—H5A	110.5	N3—C10—H10A	118.5
S1—C5—H5A	110.5	C9—C10—H10A	118.5
C4—N1—C1—C2	0.1 (6)	C7—S2—C6—C5	88.1 (4)
N1—C1—C2—C3	−0.7 (7)	C10—N3—C7—N4	1.1 (6)
C4—N2—C3—C2	−0.8 (7)	C10—N3—C7—S2	−178.7 (3)
C1—C2—C3—N2	1.0 (7)	C8—N4—C7—N3	−1.0 (7)
C1—N1—C4—N2	0.3 (6)	C8—N4—C7—S2	178.8 (3)
C1—N1—C4—S1	179.8 (3)	C6—S2—C7—N3	167.7 (3)
C3—N2—C4—N1	0.1 (7)	C6—S2—C7—N4	−12.1 (4)
C3—N2—C4—S1	−179.4 (3)	C7—N4—C8—C9	−0.6 (7)
C5—S1—C4—N1	−171.9 (3)	N4—C8—C9—C10	1.8 (7)
C5—S1—C4—N2	7.7 (4)	C7—N3—C10—C9	0.4 (6)
C4—S1—C5—C6	−83.4 (4)	C8—C9—C10—N3	−1.7 (7)
S1—C5—C6—S2	−179.0 (2)