1,4-Bis(2-pyridyl­sulfanyl)­butane

The crystal structure of the title compound, C₁₄H₁₆N₂S₂, adopts an anti conformation based on the two pyridine rings with respect to the central alkyl chain. The two terminal pyridine rings are almost parallel to each other, with a dihedral angle of 18.1 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.049
• wR factor = 0.080
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C14     ..       5.43 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

1,4-Bis(2-pyridylsulfanyl)butane

Crystal data

C14H16N2S2	F(000) = 584
Mr = 276.41	Dx = 1.281 Mg m^−3 Dm = ?NONE Mg m^−3 Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 870 reflections
a = 10.979 (5) Å	θ = 2.5–18.3°
b = 11.480 (5) Å	µ = 0.36 mm^−1
c = 11.694 (6) Å	T = 273 K
β = 103.508 (8)°	Block, colorless
V = 1433.2 (12) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	1168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −12→13
Tmin = 0.916, Tmax = 0.932	k = −10→13
5737 measured reflections	l = −11→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.01P)^2] where P = (Fo^2 + 2Fc^2)/3
2526 reflections	(Δ/σ)max = 0.002
163 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.06328 (9)	0.22782 (8)	1.00208 (9)	0.0608 (3)
S2	0.47049 (9)	−0.00077 (10)	0.79680 (8)	0.0656 (3)
N1	0.9271 (3)	0.3942 (3)	1.0724 (2)	0.0461 (8)
N2	0.6082 (3)	−0.1300 (3)	0.6851 (3)	0.0570 (9)
C1	0.9156 (3)	0.4844 (3)	1.1419 (3)	0.0550 (10)
H1	0.8386	0.5222	1.1283	0.066*
C2	1.0104 (4)	0.5249 (3)	1.2321 (3)	0.0634 (11)
H2	0.9977	0.5875	1.2784	0.076*
C3	1.1240 (4)	0.4698 (4)	1.2512 (3)	0.0724 (13)
H3	1.1903	0.4951	1.3110	0.087*
C4	1.1398 (3)	0.3772 (4)	1.1819 (3)	0.0596 (11)
H4	1.2160	0.3382	1.1942	0.071*
C5	1.0383 (4)	0.3434 (3)	1.0926 (3)	0.0438 (9)
C6	0.9123 (3)	0.2107 (3)	0.9015 (3)	0.0553 (10)
H6A	0.8706	0.2858	0.8904	0.066*
H6B	0.9248	0.1857	0.8258	0.066*
C7	0.8278 (3)	0.1240 (3)	0.9426 (3)	0.0511 (10)
H7A	0.8090	0.1522	1.0148	0.061*
H7B	0.8717	0.0504	0.9598	0.061*
C8	0.7059 (3)	0.1041 (3)	0.8516 (3)	0.0495 (10)
H8A	0.6607	0.1771	0.8361	0.059*
H8B	0.7246	0.0779	0.7787	0.059*
C9	0.6240 (3)	0.0147 (3)	0.8922 (3)	0.0563 (10)
H9A	0.6150	0.0363	0.9700	0.068*
H9B	0.6660	−0.0602	0.8988	0.068*
C10	0.4966 (4)	−0.0825 (3)	0.6781 (3)	0.0441 (9)
C11	0.3970 (3)	−0.0951 (3)	0.5810 (4)	0.0563 (11)
H11	0.3199	−0.0608	0.5797	0.068*
C12	0.4142 (4)	−0.1588 (3)	0.4875 (4)	0.0680 (12)
H12	0.3485	−0.1693	0.4218	0.082*
C13	0.5298 (5)	−0.2073 (3)	0.4912 (4)	0.0734 (13)
H13	0.5445	−0.2494	0.4279	0.088*
C14	0.6226 (4)	−0.1915 (3)	0.5916 (4)	0.0683 (12)
H14	0.7002	−0.2255	0.5949	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (6)	0.0531 (6)	0.0825 (7)	−0.0004 (5)	0.0170 (5)	−0.0079 (6)
S2	0.0432 (6)	0.0923 (8)	0.0608 (6)	0.0011 (6)	0.0110 (5)	−0.0090 (6)
N1	0.040 (2)	0.050 (2)	0.0494 (19)	0.0021 (15)	0.0125 (16)	−0.0009 (17)
N2	0.046 (2)	0.057 (2)	0.067 (2)	0.0022 (17)	0.0115 (18)	−0.0081 (18)
C1	0.049 (3)	0.057 (3)	0.063 (3)	0.005 (2)	0.022 (2)	0.010 (2)
C2	0.079 (3)	0.057 (3)	0.061 (3)	−0.014 (3)	0.029 (3)	−0.012 (2)
C3	0.061 (3)	0.095 (4)	0.059 (3)	−0.022 (3)	0.010 (2)	−0.011 (3)
C4	0.037 (3)	0.078 (3)	0.061 (3)	−0.004 (2)	0.007 (2)	0.003 (2)
C5	0.041 (3)	0.045 (2)	0.049 (2)	−0.006 (2)	0.016 (2)	0.0079 (18)
C6	0.065 (3)	0.048 (2)	0.054 (2)	−0.007 (2)	0.015 (2)	−0.010 (2)
C7	0.054 (3)	0.044 (2)	0.054 (2)	−0.0052 (19)	0.011 (2)	0.0007 (19)
C8	0.056 (3)	0.049 (3)	0.043 (2)	−0.0006 (19)	0.009 (2)	−0.0025 (18)
C9	0.055 (2)	0.069 (3)	0.042 (2)	−0.010 (2)	0.0065 (18)	−0.002 (2)
C10	0.039 (2)	0.044 (2)	0.049 (3)	−0.0055 (19)	0.009 (2)	0.0054 (18)
C11	0.045 (3)	0.058 (3)	0.061 (3)	−0.001 (2)	0.003 (2)	0.013 (2)
C12	0.079 (4)	0.062 (3)	0.056 (3)	−0.019 (3)	0.001 (3)	0.003 (2)
C13	0.097 (4)	0.053 (3)	0.076 (3)	−0.001 (3)	0.031 (3)	−0.007 (2)
C14	0.057 (3)	0.058 (3)	0.089 (3)	0.006 (2)	0.013 (3)	−0.004 (3)

Geometric parameters (Å, º)

S1—C5	1.758 (3)	C6—H6B	0.9700
S1—C6	1.806 (3)	C7—C8	1.520 (4)
S2—C9	1.800 (3)	C7—H7A	0.9700
S2—C10	1.754 (3)	C7—H7B	0.9700
N1—C5	1.324 (4)	C8—C9	1.511 (4)
N1—C1	1.340 (4)	C8—H8A	0.9700
N2—C10	1.326 (4)	C8—H8B	0.9700
N2—C14	1.341 (4)	C9—H9A	0.9700
C1—C2	1.379 (4)	C9—H9B	0.9700
C1—H1	0.9300	C10—C11	1.388 (4)
C2—C3	1.369 (5)	C11—C12	1.364 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.372 (5)	C12—C13	1.377 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.393 (4)	C13—C14	1.375 (5)
C4—H4	0.9300	C13—H13	0.9300
C6—C7	1.514 (4)	C14—H14	0.9300
C6—H6A	0.9700
C5—S1—C6	103.1 (2)	C8—C7—H7B	109.1
C9—S2—C10	103.9 (2)	H7A—C7—H7B	107.9
C1—N1—C5	116.5 (3)	C9—C8—C7	111.9 (3)
C10—N2—C14	116.7 (3)	C9—C8—H8A	109.2
N1—C1—C2	124.3 (3)	C7—C8—H8A	109.2
N1—C1—H1	117.9	C9—C8—H8B	109.2
C2—C1—H1	117.9	C7—C8—H8B	109.2
C3—C2—C1	117.7 (4)	H8A—C8—H8B	107.9
C3—C2—H2	121.1	C8—C9—S2	114.3 (2)
C1—C2—H2	121.1	C8—C9—H9A	108.7
C2—C3—C4	119.8 (4)	S2—C9—H9A	108.7
C2—C3—H3	120.1	C8—C9—H9B	108.7
C4—C3—H3	120.1	S2—C9—H9B	108.7
C3—C4—C5	118.0 (4)	H9A—C9—H9B	107.6
C3—C4—H4	121.0	N2—C10—C11	123.3 (3)
C5—C4—H4	121.0	N2—C10—S2	119.4 (3)
N1—C5—C4	123.6 (3)	C11—C10—S2	117.4 (3)
N1—C5—S1	119.5 (3)	C12—C11—C10	118.8 (4)
C4—C5—S1	116.9 (3)	C12—C11—H11	120.6
C7—C6—S1	113.7 (2)	C10—C11—H11	120.6
C7—C6—H6A	108.8	C11—C12—C13	119.3 (4)
S1—C6—H6A	108.8	C11—C12—H12	120.3
C7—C6—H6B	108.8	C13—C12—H12	120.3
S1—C6—H6B	108.8	C14—C13—C12	117.9 (4)
H6A—C6—H6B	107.7	C14—C13—H13	121.1
C6—C7—C8	112.4 (3)	C12—C13—H13	121.1
C6—C7—H7A	109.1	N2—C14—C13	124.1 (4)
C8—C7—H7A	109.1	N2—C14—H14	118.0
C6—C7—H7B	109.1	C13—C14—H14	118.0
C5—N1—C1—C2	−1.1 (5)	C7—C8—C9—S2	173.0 (2)
N1—C1—C2—C3	0.6 (5)	C10—S2—C9—C8	76.7 (3)
C1—C2—C3—C4	−0.4 (5)	C14—N2—C10—C11	0.8 (5)
C2—C3—C4—C5	0.7 (5)	C14—N2—C10—S2	−180.0 (2)
C1—N1—C5—C4	1.4 (5)	C9—S2—C10—N2	9.5 (3)
C1—N1—C5—S1	−177.6 (2)	C9—S2—C10—C11	−171.2 (3)
C3—C4—C5—N1	−1.3 (5)	N2—C10—C11—C12	−0.4 (5)
C3—C4—C5—S1	177.8 (3)	S2—C10—C11—C12	−179.7 (3)
C6—S1—C5—N1	−1.4 (3)	C10—C11—C12—C13	−0.8 (5)
C6—S1—C5—C4	179.5 (3)	C11—C12—C13—C14	1.6 (5)
C5—S1—C6—C7	−91.4 (2)	C10—N2—C14—C13	0.1 (5)
S1—C6—C7—C8	−175.2 (2)	C12—C13—C14—N2	−1.3 (6)
C6—C7—C8—C9	178.3 (3)