2,2′-(1,4-Butane­diyl­di­thio)-1,3-di­thia­zole

The title compound, C₁₀H₁₄N₂S₄, was synthesized by the reaction of the potassium salt of 2-thio­thia­zole and 1,4-di­bromo­butane. The two 2-thia­zole­thio groups are related by a center of symmetry. The plane defined by the butyl carbon chain is approximately orthogonal to the thia­zole plane, with a dihedral angle of 84.7 (8)°. Intermolecular S...S interactions between adjacent mol­ecules link them into infinite chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.076
• Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

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

2,2'-[(1,4-Butanediyl)dithio]dithiazole

Crystal data

C10H12N2S4	F(000) = 300
Mr = 288.46	Dx = 1.459 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 754 reflections
a = 6.067 (2) Å	θ = 3.0–25.9°
b = 14.099 (5) Å	µ = 0.70 mm^−1
c = 7.733 (3) Å	T = 293 K
β = 97.101 (6)°	Needle, colourless
V = 656.4 (4) Å^3	0.56 × 0.32 × 0.20 mm
Z = 2

Data collection

Bruker CCD area-detector diffractometer	1336 independent reflections
Radiation source: fine-focus sealed tube	1021 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1997)	h = −4→7
Tmin = 0.772, Tmax = 0.870	k = −17→17
3664 measured reflections	l = −9→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0344P)^2 + 0.1369P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.20 e Å^−3
1336 reflections	Δρmin = −0.18 e Å^−3
74 parameters

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 > 2σ(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	0.16147 (9)	0.02272 (4)	0.82924 (7)	0.0476 (2)
S2	0.11393 (9)	0.18759 (4)	1.06770 (7)	0.0509 (2)
N1	0.4513 (3)	0.16970 (13)	0.8982 (2)	0.0495 (5)
C1	0.3181 (4)	0.27241 (15)	1.0963 (3)	0.0513 (5)
H1	0.3168	0.3251	1.1686	0.062*
C2	0.4791 (4)	0.25157 (16)	0.9995 (3)	0.0574 (6)
H2	0.6039	0.2899	0.9997	0.069*
C3	0.2654 (3)	0.12949 (13)	0.9224 (2)	0.0371 (4)
C4	0.3962 (4)	−0.01837 (14)	0.7242 (3)	0.0445 (5)
H4A	0.5323	−0.0006	0.7960	0.053*
H4B	0.3916	−0.0871	0.7182	0.053*
C5	0.4029 (3)	0.02053 (13)	0.5416 (2)	0.0388 (5)
H5A	0.4164	0.0891	0.5470	0.047*
H5B	0.2650	0.0052	0.4697	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0534 (3)	0.0478 (3)	0.0452 (3)	−0.0087 (2)	0.0204 (2)	−0.0120 (2)
S2	0.0505 (4)	0.0518 (3)	0.0532 (4)	0.0016 (3)	0.0181 (3)	−0.0147 (2)
N1	0.0503 (11)	0.0526 (11)	0.0481 (10)	−0.0097 (9)	0.0158 (9)	−0.0063 (8)
C1	0.0624 (14)	0.0406 (11)	0.0501 (12)	0.0031 (11)	0.0039 (11)	−0.0073 (10)
C2	0.0592 (14)	0.0516 (13)	0.0623 (14)	−0.0172 (11)	0.0114 (12)	−0.0056 (11)
C3	0.0436 (11)	0.0385 (10)	0.0301 (9)	0.0043 (9)	0.0085 (8)	−0.0001 (8)
C4	0.0577 (13)	0.0414 (11)	0.0364 (10)	0.0088 (10)	0.0140 (9)	−0.0022 (9)
C5	0.0459 (11)	0.0388 (11)	0.0322 (9)	0.0056 (9)	0.0062 (9)	−0.0019 (8)

Geometric parameters (Å, º)

S1—C3	1.752 (2)	C2—H2	0.9300
S1—C4	1.819 (2)	C4—C5	1.520 (3)
S2—C1	1.717 (2)	C4—H4A	0.9700
S2—C3	1.7413 (18)	C4—H4B	0.9700
N1—C3	1.297 (3)	C5—C5^i	1.524 (4)
N1—C2	1.394 (3)	C5—H5A	0.9700
C1—C2	1.335 (3)	C5—H5B	0.9700
C1—H1	0.9300
C3—S1—C4	101.28 (10)	C5—C4—S1	114.36 (14)
C1—S2—C3	88.91 (10)	C5—C4—H4A	108.7
C3—N1—C2	109.12 (17)	S1—C4—H4A	108.7
C2—C1—S2	109.93 (17)	C5—C4—H4B	108.7
C2—C1—H1	125.0	S1—C4—H4B	108.7
S2—C1—H1	125.0	H4A—C4—H4B	107.6
C1—C2—N1	116.9 (2)	C4—C5—C5^i	111.5 (2)
C1—C2—H2	121.6	C4—C5—H5A	109.3
N1—C2—H2	121.6	C5^i—C5—H5A	109.3
N1—C3—S2	115.19 (15)	C4—C5—H5B	109.3
N1—C3—S1	126.24 (14)	C5^i—C5—H5B	109.3
S2—C3—S1	118.54 (11)	H5A—C5—H5B	108.0
C3—S2—C1—C2	−0.33 (18)	C1—S2—C3—S1	178.20 (13)
S2—C1—C2—N1	0.4 (3)	C4—S1—C3—N1	7.6 (2)
C3—N1—C2—C1	−0.3 (3)	C4—S1—C3—S2	−170.23 (11)
C2—N1—C3—S2	0.0 (2)	C3—S1—C4—C5	−86.26 (16)
C2—N1—C3—S1	−177.82 (16)	S1—C4—C5—C5^i	−177.24 (18)
C1—S2—C3—N1	0.17 (17)

Symmetry code: (i) −x+1, −y, −z+1.