Butane-1,4-diyl bis-(pyridine-3-carboxyl-ate).

Mol-ecules of the title compound (alternative name: butane-1,4-diyl dinicotinate), C(16)H(16)N(2)O(4), lie on a inversion centre, located at the mid-point of the central C-C bond of the aliphatic chain, giving one half-mol-ecule per asymmetric unit. The butane chain adopts an all-trans conformation. The dihedral angle between the mean plane of the butane-3-carboxyl-ate group [for the non-H atoms, maximum deviation = 0.0871 (15) Å] and the pyridine ring is 10.83 (7)°. In the crystal, mol-ecules lie in planes parallel to (122). The structure features weak π-π inter-actions with a centroid-centroid distance of 3.9281 (11) Å.

Related literature

For the crystal structures of compounds with related ligands, see: Brito et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Triclinic,

a = 6.7186 (10) Å

b = 7.6942 (12) Å

c = 8.2462 (13) Å

α = 65.290 (11)°

β = 75.499 (12)°

γ = 68.207 (11)°

V = 357.28 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.29 × 0.25 × 0.18 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA and X-RED32; Stoe & Cie, 2001 ▶) T min = 0.971, T max = 0.982

6958 measured reflections

1347 independent reflections

1171 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.13

1347 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202260X/su2433sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202260X/su2433Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202260X/su2433Isup3.cml

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

C16H16N2O4	Z = 1
Mr = 300.31	F(000) = 158
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7186 (10) Å	Cell parameters from 9708 reflections
b = 7.6942 (12) Å	θ = 3.3–26.0°
c = 8.2462 (13) Å	µ = 0.10 mm−1
α = 65.290 (11)°	T = 173 K
β = 75.499 (12)°	Block, colourless
γ = 68.207 (11)°	0.29 × 0.25 × 0.18 mm
V = 357.28 (10) Å3

Stoe IPDS II two-circle diffractometer	1347 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1171 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.035
ω scans	θmax = 25.6°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA and X-RED32; Stoe & Cie, 2001)	h = −7→8
Tmin = 0.971, Tmax = 0.982	k = −9→9
6958 measured reflections	l = −10→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0318P)2 + 0.1244P] where P = (Fo2 + 2Fc2)/3
1347 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. Spectroscopic details for the title compound:IR (KBr): 3087 (w), 1713 (s), 1589 (m), 1473 (w), 1294 (s), 1195 (s), 741(m), cm-1.

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
O1	0.31502 (17)	1.03384 (16)	0.27815 (14)	0.0328 (3)
O2	0.66529 (16)	0.87068 (16)	0.31015 (13)	0.0279 (3)
C1	0.4547 (2)	0.8987 (2)	0.36257 (19)	0.0238 (3)
C3	0.7222 (2)	1.0083 (2)	0.13405 (19)	0.0260 (3)
H3A	0.6772	1.1460	0.1347	0.031*
H3B	0.6496	1.0104	0.0423	0.031*
C4	0.9628 (2)	0.9344 (2)	0.09306 (19)	0.0285 (4)
H4A	1.0063	0.7942	0.0991	0.034*
H4B	1.0334	0.9360	0.1842	0.034*
C11	0.4134 (2)	0.7418 (2)	0.53811 (19)	0.0242 (3)
C12	0.5775 (3)	0.6012 (2)	0.64157 (19)	0.0285 (3)
H12	0.7208	0.6067	0.5976	0.034*
N13	0.5455 (2)	0.4591 (2)	0.79911 (17)	0.0339 (3)
C14	0.3422 (3)	0.4555 (2)	0.8578 (2)	0.0325 (4)
H14	0.3158	0.3561	0.9703	0.039*
C15	0.1685 (3)	0.5879 (2)	0.7646 (2)	0.0320 (4)
H15	0.0269	0.5788	0.8116	0.038*
C16	0.2046 (2)	0.7336 (2)	0.6017 (2)	0.0286 (4)
H16	0.0883	0.8268	0.5342	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0257 (6)	0.0321 (6)	0.0288 (6)	−0.0071 (5)	−0.0041 (5)	−0.0009 (5)
O2	0.0222 (5)	0.0301 (6)	0.0229 (5)	−0.0088 (4)	−0.0001 (4)	−0.0023 (4)
C1	0.0231 (7)	0.0254 (7)	0.0224 (7)	−0.0086 (6)	−0.0017 (6)	−0.0075 (6)
C3	0.0264 (8)	0.0274 (7)	0.0194 (7)	−0.0117 (6)	0.0004 (6)	−0.0026 (6)
C4	0.0246 (8)	0.0301 (8)	0.0255 (8)	−0.0097 (6)	−0.0014 (6)	−0.0047 (7)
C11	0.0268 (8)	0.0216 (7)	0.0230 (7)	−0.0072 (6)	0.0006 (6)	−0.0090 (6)
C12	0.0260 (8)	0.0298 (8)	0.0248 (8)	−0.0075 (6)	0.0000 (6)	−0.0077 (6)
N13	0.0331 (7)	0.0303 (7)	0.0271 (7)	−0.0057 (6)	−0.0022 (6)	−0.0039 (6)
C14	0.0397 (9)	0.0266 (8)	0.0226 (8)	−0.0121 (7)	0.0039 (7)	−0.0032 (6)
C15	0.0293 (8)	0.0314 (8)	0.0308 (8)	−0.0135 (7)	0.0054 (6)	−0.0082 (7)
C16	0.0261 (8)	0.0264 (8)	0.0279 (8)	−0.0065 (6)	−0.0024 (6)	−0.0065 (6)

O1—C1	1.2017 (18)	C11—C16	1.384 (2)
O2—C1	1.3342 (18)	C11—C12	1.389 (2)
O2—C3	1.4538 (17)	C12—N13	1.333 (2)
C1—C11	1.4886 (19)	C12—H12	0.9500
C3—C4	1.502 (2)	N13—C14	1.337 (2)
C3—H3A	0.9900	C14—C15	1.379 (2)
C3—H3B	0.9900	C14—H14	0.9500
C4—C4i	1.523 (3)	C15—C16	1.378 (2)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—H16	0.9500
C1—O2—C3	115.98 (12)	C16—C11—C12	118.20 (14)
O1—C1—O2	124.15 (13)	C16—C11—C1	119.43 (13)
O1—C1—C11	123.99 (13)	C12—C11—C1	122.38 (13)
O2—C1—C11	111.87 (12)	N13—C12—C11	123.74 (14)
O2—C3—C4	106.96 (12)	N13—C12—H12	118.1
O2—C3—H3A	110.3	C11—C12—H12	118.1
C4—C3—H3A	110.3	C12—N13—C14	116.78 (14)
O2—C3—H3B	110.3	N13—C14—C15	123.82 (14)
C4—C3—H3B	110.3	N13—C14—H14	118.1
H3A—C3—H3B	108.6	C15—C14—H14	118.1
C3—C4—C4i	110.76 (16)	C16—C15—C14	118.61 (15)
C3—C4—H4A	109.5	C16—C15—H15	120.7
C4i—C4—H4A	109.5	C14—C15—H15	120.7
C3—C4—H4B	109.5	C15—C16—C11	118.86 (15)
C4i—C4—H4B	109.5	C15—C16—H16	120.6
H4A—C4—H4B	108.1	C11—C16—H16	120.6
C3—O2—C1—O1	−3.9 (2)	C16—C11—C12—N13	−0.3 (2)
C3—O2—C1—C11	175.89 (12)	C1—C11—C12—N13	−179.97 (15)
C1—O2—C3—C4	−173.02 (12)	C11—C12—N13—C14	−0.2 (2)
O2—C3—C4—C4i	177.89 (15)	C12—N13—C14—C15	0.5 (2)
O1—C1—C11—C16	7.7 (2)	N13—C14—C15—C16	−0.4 (3)
O2—C1—C11—C16	−172.10 (13)	C14—C15—C16—C11	−0.1 (2)
O1—C1—C11—C12	−172.59 (15)	C12—C11—C16—C15	0.4 (2)
O2—C1—C11—C12	7.61 (19)	C1—C11—C16—C15	−179.89 (14)