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

The mol-ecule of the title compound, C(16)H(16)N(2)O(4), lies about an inversion centre; the butane chain adopts an extended zigzag conformation. The dihedral angle between the pyridine ring and the adjacent COO group is 3.52 (s14)°.

Related literature

For a related structure, see: Brito et al. (2010 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Monoclinic,

a = 7.8519 (5) Å

b = 10.5284 (6) Å

c = 8.9121 (4) Å

β = 91.770 (5)°

V = 736.39 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.13 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.840, T max = 1.000

2431 measured reflections

1303 independent reflections

754 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 0.87

1303 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023646/ng5184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023646/ng5184Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023646/ng5184Isup3.cml

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

C16H16N2O4	F(000) = 316
Mr = 300.31	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 852 reflections
a = 7.8519 (5) Å	θ = 2.6–28.6°
b = 10.5284 (6) Å	µ = 0.10 mm−1
c = 8.9121 (4) Å	T = 293 K
β = 91.770 (5)°	Plate, colorless
V = 736.39 (7) Å3	0.35 × 0.13 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur Eos diffractometer	1303 independent reflections
Radiation source: fine-focus sealed tube	754 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→7
Tmin = 0.840, Tmax = 1.000	l = −6→10
2431 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3
1303 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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	0.33092 (14)	0.50761 (11)	0.18817 (12)	0.0510 (4)
C2	0.21740 (19)	0.51211 (16)	−0.05823 (17)	0.0389 (4)
C1	0.2787 (2)	0.58307 (18)	0.0775 (2)	0.0466 (5)
O2	0.2806 (2)	0.69674 (13)	0.08561 (15)	0.0789 (5)
C3	0.1504 (2)	0.57907 (18)	−0.17878 (19)	0.0504 (5)
H3	0.1438	0.6672	−0.1753	0.060*
C6	0.2231 (2)	0.38214 (18)	−0.06986 (19)	0.0529 (5)
H6	0.2663	0.3327	0.0090	0.063*
N1	0.0981 (2)	0.39039 (17)	−0.31796 (17)	0.0607 (5)
C4	0.0936 (2)	0.5144 (2)	−0.3041 (2)	0.0546 (6)
H4	0.0491	0.5614	−0.3844	0.065*
C7	0.3923 (2)	0.57013 (18)	0.32514 (19)	0.0539 (6)
H7A	0.3001	0.6162	0.3705	0.065*
H7B	0.4819	0.6300	0.3026	0.065*
C8	0.4589 (2)	0.47077 (18)	0.42959 (18)	0.0465 (5)
H8A	0.5424	0.4195	0.3792	0.056*
H8B	0.3663	0.4156	0.4577	0.056*
C5	0.1632 (3)	0.3269 (2)	−0.2011 (2)	0.0645 (6)
H5	0.1688	0.2389	−0.2084	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0716 (8)	0.0474 (8)	0.0329 (7)	0.0001 (6)	−0.0175 (6)	−0.0006 (6)
C2	0.0430 (10)	0.0424 (10)	0.0310 (9)	−0.0030 (8)	−0.0023 (8)	−0.0006 (9)
C1	0.0597 (12)	0.0440 (11)	0.0356 (10)	−0.0006 (10)	−0.0063 (9)	0.0026 (10)
O2	0.1401 (14)	0.0422 (9)	0.0522 (9)	−0.0013 (9)	−0.0322 (8)	−0.0016 (7)
C3	0.0659 (13)	0.0436 (11)	0.0410 (11)	−0.0005 (10)	−0.0108 (10)	0.0029 (9)
C6	0.0726 (13)	0.0466 (12)	0.0386 (11)	0.0012 (10)	−0.0110 (10)	0.0022 (10)
N1	0.0755 (12)	0.0600 (12)	0.0454 (10)	−0.0034 (9)	−0.0162 (9)	−0.0042 (9)
C4	0.0683 (14)	0.0590 (13)	0.0353 (10)	0.0028 (11)	−0.0156 (9)	0.0027 (10)
C7	0.0710 (13)	0.0542 (13)	0.0353 (10)	−0.0022 (10)	−0.0185 (10)	−0.0059 (9)
C8	0.0540 (11)	0.0516 (11)	0.0331 (9)	−0.0001 (9)	−0.0111 (8)	−0.0010 (9)
C5	0.0927 (16)	0.0447 (12)	0.0553 (13)	−0.0060 (11)	−0.0134 (12)	−0.0084 (11)

O1—C1	1.322 (2)	N1—C4	1.312 (2)
O1—C7	1.4558 (19)	N1—C5	1.326 (2)
C2—C6	1.373 (2)	C4—H4	0.9300
C2—C3	1.376 (2)	C7—C8	1.485 (2)
C2—C1	1.489 (2)	C7—H7A	0.9700
C1—O2	1.199 (2)	C7—H7B	0.9700
C3—C4	1.371 (2)	C8—C8i	1.523 (3)
C3—H3	0.9300	C8—H8A	0.9700
C6—C5	1.376 (2)	C8—H8B	0.9700
C6—H6	0.9300	C5—H5	0.9300
C1—O1—C7	116.16 (14)	C3—C4—H4	117.9
C6—C2—C3	117.66 (16)	O1—C7—C8	107.95 (14)
C6—C2—C1	123.43 (17)	O1—C7—H7A	110.1
C3—C2—C1	118.91 (17)	C8—C7—H7A	110.1
O2—C1—O1	123.51 (18)	O1—C7—H7B	110.1
O2—C1—C2	123.57 (18)	C8—C7—H7B	110.1
O1—C1—C2	112.93 (16)	H7A—C7—H7B	108.4
C4—C3—C2	119.25 (17)	C7—C8—C8i	111.34 (19)
C4—C3—H3	120.4	C7—C8—H8A	109.4
C2—C3—H3	120.4	C8i—C8—H8A	109.4
C2—C6—C5	118.30 (18)	C7—C8—H8B	109.4
C2—C6—H6	120.9	C8i—C8—H8B	109.4
C5—C6—H6	120.9	H8A—C8—H8B	108.0
C4—N1—C5	115.97 (17)	N1—C5—C6	124.61 (18)
N1—C4—C3	124.21 (18)	N1—C5—H5	117.7
N1—C4—H4	117.9	C6—C5—H5	117.7
C7—O1—C1—O2	0.3 (3)	C3—C2—C6—C5	0.6 (3)
C7—O1—C1—C2	−179.81 (14)	C1—C2—C6—C5	−179.81 (17)
C6—C2—C1—O2	176.70 (18)	C5—N1—C4—C3	−0.3 (3)
C3—C2—C1—O2	−3.7 (3)	C2—C3—C4—N1	0.2 (3)
C6—C2—C1—O1	−3.2 (2)	C1—O1—C7—C8	−175.01 (15)
C3—C2—C1—O1	176.39 (15)	O1—C7—C8—C8i	174.67 (17)
C6—C2—C3—C4	−0.3 (3)	C4—N1—C5—C6	0.6 (3)
C1—C2—C3—C4	−179.94 (16)	C2—C6—C5—N1	−0.7 (3)