Ethane-1,2-diyl bis-(pyridine-3-car-box-ylate).

The title compound, C(14)H(12)N(2)O(4), has twofold imposed crystallographic symmetry in the solid state. The asymmetric unit contains one half-mol-ecule. An intra-molecular C-H⋯O hydrogen bond is formed between the carboxyl-ate O group and one H atom of the aromatic ring such that a five-membered ring is formed. The angle between the planes of symmetry-related aromatic rings is 44.71 (19)°.

Related literature

For the synthesis of ditopic flexible linkers, see: Chatterjee et al. (2004 ▶). For the potential of coordination polymers based on this multitopic bridging ligand and metal centers as functional materials, see: Huang et al. (2007 ▶). For applications, see: Matsuda et al. (2005 ▶); Wu et al. (2005 ▶); Xiang et al. (2005 ▶). For bond-length data, see: Allen (2002 ▶).

Experimental

Crystal data

C14H12N2O4

M = 272.26

Orthorhombic,

a = 4.0740 (14) Å

b = 21.3404 (7) Å

c = 7.395 (6) Å

V = 642.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.19 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

2298 measured reflections

874 independent reflections

694 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.131

S = 1.27

874 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052106/om2303sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052106/om2303Isup2.hkl

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

C14H12N2O4	F(000) = 284
Mr = 272.26	Dx = 1.406 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1704 reflections
a = 4.0740 (14) Å	θ = 1.9–27.5°
b = 21.3404 (7) Å	µ = 0.11 mm−1
c = 7.395 (6) Å	T = 293 K
V = 642.9 (6) Å3	Prismatic, colourless
Z = 2	0.19 × 0.10 × 0.08 mm

Nonius KappaCCD area-detector diffractometer	694 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 27.6°, θmin = 1.9°
φ scans, and ω scans with κ offsets	h = −5→0
2298 measured reflections	k = −27→27
874 independent reflections	l = −9→9

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.27	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.2469P] where P = (Fo2 + 2Fc2)/3
874 reflections	(Δ/σ)max = 0.002
91 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
O1	−0.1685 (7)	0.44509 (9)	−0.0673 (3)	0.0399 (6)
O2	−0.1110 (9)	0.34487 (11)	−0.1477 (3)	0.0619 (9)
N1	−0.5385 (10)	0.40255 (14)	0.4274 (4)	0.0574 (10)
C1	−0.3638 (9)	0.36912 (14)	0.1334 (4)	0.0330 (8)
C2	−0.3991 (10)	0.41380 (16)	0.2682 (5)	0.0458 (10)
H2	−0.3207	0.454	0.2458	0.055*
C3	−0.6491 (10)	0.34439 (17)	0.4541 (5)	0.0497 (10)
H3	−0.7497	0.3355	0.564	0.06*
C4	−0.6241 (11)	0.29697 (17)	0.3305 (4)	0.0462 (10)
H4	−0.7058	0.2573	0.3562	0.055*
C5	−0.4756 (10)	0.30923 (15)	0.1671 (4)	0.0416 (9)
H5	−0.451	0.2778	0.0812	0.05*
C6	−0.2039 (9)	0.38335 (15)	−0.0413 (4)	0.0365 (8)
C7	0.0000 (10)	0.46502 (15)	−0.2299 (4)	0.0408 (9)
H7A	−0.1124	0.4492	−0.3362	0.049*
H7B	0.2233	0.4493	−0.2306	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0527 (15)	0.0300 (12)	0.0371 (11)	−0.0025 (11)	0.0110 (13)	−0.0014 (10)
O2	0.102 (2)	0.0365 (13)	0.0474 (13)	0.0018 (16)	0.0250 (17)	−0.0097 (12)
N1	0.077 (2)	0.051 (2)	0.0441 (16)	−0.0096 (19)	0.015 (2)	−0.0089 (15)
C1	0.038 (2)	0.0291 (15)	0.0321 (15)	0.0021 (15)	−0.0016 (16)	−0.0008 (12)
C2	0.058 (3)	0.0334 (18)	0.0457 (19)	−0.0051 (19)	0.008 (2)	−0.0066 (15)
C3	0.057 (3)	0.054 (2)	0.0380 (18)	−0.009 (2)	0.008 (2)	0.0021 (17)
C4	0.055 (3)	0.0358 (18)	0.0478 (19)	−0.0023 (18)	0.003 (2)	0.0044 (15)
C5	0.049 (2)	0.0331 (17)	0.0423 (17)	−0.0009 (18)	0.0011 (19)	−0.0043 (15)
C6	0.042 (2)	0.0318 (17)	0.0360 (16)	0.0001 (16)	−0.0020 (17)	−0.0014 (14)
C7	0.047 (2)	0.0460 (18)	0.0294 (15)	−0.0102 (19)	0.0023 (18)	−0.0013 (14)

O1—C6	1.339 (4)	C3—C4	1.368 (5)
O1—C7	1.449 (4)	C3—H3	0.93
O2—C6	1.198 (4)	C4—C5	1.376 (5)
N1—C2	1.330 (5)	C4—H4	0.93
N1—C3	1.335 (5)	C5—H5	0.93
C1—C5	1.380 (4)	C7—C7i	1.493 (7)
C1—C2	1.387 (4)	C7—H7A	0.97
C1—C6	1.478 (4)	C7—H7B	0.97
C2—H2	0.93
C6—O1—C7	117.3 (2)	C5—C4—H4	120.7
C2—N1—C3	116.3 (3)	C4—C5—C1	118.7 (3)
C5—C1—C2	118.2 (3)	C4—C5—H5	120.6
C5—C1—C6	119.6 (3)	C1—C5—H5	120.6
C2—C1—C6	122.2 (3)	O2—C6—O1	123.1 (3)
N1—C2—C1	123.8 (3)	O2—C6—C1	124.9 (3)
N1—C2—H2	118.1	O1—C6—C1	112.0 (3)
C1—C2—H2	118.1	O1—C7—C7i	107.1 (3)
N1—C3—C4	124.3 (3)	O1—C7—H7A	110.3
N1—C3—H3	117.8	C7i—C7—H7A	110.3
C4—C3—H3	117.8	O1—C7—H7B	110.3
C3—C4—C5	118.6 (3)	C7i—C7—H7B	110.3
C3—C4—H4	120.7	H7A—C7—H7B	108.6
C3—N1—C2—C1	−0.2 (6)	C7—O1—C6—O2	−2.0 (5)
C5—C1—C2—N1	−0.9 (6)	C7—O1—C6—C1	177.0 (3)
C6—C1—C2—N1	−179.3 (4)	C5—C1—C6—O2	−13.3 (6)
C2—N1—C3—C4	0.7 (6)	C2—C1—C6—O2	165.1 (4)
N1—C3—C4—C5	0.1 (7)	C5—C1—C6—O1	167.8 (3)
C3—C4—C5—C1	−1.3 (6)	C2—C1—C6—O1	−13.9 (5)
C2—C1—C5—C4	1.7 (6)	C6—O1—C7—C7i	178.5 (4)
C6—C1—C5—C4	−179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.40	2.735 (5)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.40	2.735 (5)	101