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

The title compound, C(15)H(14)N(2)O(4), has a trans-gauche [O/C/C/C-O/C/C/C] (TG) conformation. The angle between the planes of aromatic rings is 76.4 (3)°. The crystal structure is stabilized by van der Waals inter-actions and C-H⋯O hydrogen bonds. The crystal used was a non-merohedral twin with a fractional contribution of the minor component of 0.443 (5).

Related literature

For conformation definitions, see: Carlucci et al. (2002 ▶). For applications of crystalline nanoporous coordination polymers, see Matsuda et al. (2005 ▶); Wu et al. (2005 ▶); Xiang et al. (2005 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Triclinic,

a = 4.4797 (11) Å

b = 10.911 (3) Å

c = 14.842 (4) Å

α = 104.41 (2)°

β = 95.90 (2)°

γ = 100.90 (2)°

V = 681.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.22 × 0.14 × 0.07 mm

Data collection

Stoe IPDS II two-circle diffractometer

8629 measured reflections

2558 independent reflections

1382 reflections with I > 2σ(I)

R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.109

wR(F 2) = 0.276

S = 1.49

2558 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.46 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008810/om2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008810/om2324Isup2.hkl

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

C15H14N2O4	Z = 2
Mr = 286.28	F(000) = 300
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.4797 (11) Å	Cell parameters from 3924 reflections
b = 10.911 (3) Å	θ = 3.9–25.8°
c = 14.842 (4) Å	µ = 0.10 mm−1
α = 104.41 (2)°	T = 173 K
β = 95.90 (2)°	Plate, colourless
γ = 100.90 (2)°	0.22 × 0.14 × 0.07 mm
V = 681.3 (3) Å3

Stoe IPDS II two-circle diffractometer	1382 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.119
graphite	θmax = 26.0°, θmin = 3.8°
ω scans	h = −5→5
8629 measured reflections	k = −13→12
2558 independent reflections	l = −12→17

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)] = 0.109	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.276	H-atom parameters constrained
S = 1.49	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
2558 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.8187 (10)	0.2723 (4)	0.2445 (4)	0.0458 (12)
O2	0.6697 (13)	0.0749 (5)	0.1430 (4)	0.0637 (16)
O3	1.1653 (9)	0.2272 (4)	0.5109 (3)	0.0405 (11)
O4	1.2061 (11)	0.4252 (4)	0.6081 (4)	0.0540 (14)
C1	0.6560 (14)	0.1865 (6)	0.1644 (5)	0.0434 (17)
C2	1.0002 (15)	0.2161 (6)	0.3054 (5)	0.0434 (16)
H2A	1.1296	0.1648	0.2688	0.052*
H2B	0.8629	0.1587	0.3334	0.052*
C3	1.2023 (14)	0.3317 (6)	0.3827 (5)	0.0448 (17)
H3A	1.3515	0.3838	0.3543	0.054*
H3B	1.0718	0.3881	0.4135	0.054*
C4	1.3748 (14)	0.2826 (7)	0.4557 (5)	0.0445 (17)
H4A	1.4795	0.2160	0.4234	0.053*
H4B	1.5339	0.3554	0.4981	0.053*
C5	1.0994 (13)	0.3111 (6)	0.5848 (5)	0.0439 (17)
C11	0.4701 (14)	0.2473 (6)	0.1081 (5)	0.0420 (16)
C12	0.4516 (15)	0.3777 (6)	0.1359 (5)	0.0451 (17)
H12	0.5646	0.4308	0.1948	0.054*
N13	0.2835 (15)	0.4308 (6)	0.0838 (5)	0.0568 (17)
C14	0.1172 (16)	0.3544 (7)	0.0009 (6)	0.0538 (19)
H14	−0.0070	0.3904	−0.0367	0.065*
C15	0.1253 (17)	0.2229 (7)	−0.0306 (6)	0.055 (2)
H15	0.0121	0.1712	−0.0899	0.066*
C16	0.2940 (17)	0.1699 (7)	0.0235 (6)	0.0516 (19)
H16	0.2923	0.0800	0.0037	0.062*
C21	0.8829 (13)	0.2446 (6)	0.6378 (5)	0.0386 (15)
C22	0.7613 (14)	0.1126 (6)	0.6107 (6)	0.0472 (18)
H22	0.8192	0.0626	0.5560	0.057*
N23	0.5693 (13)	0.0501 (6)	0.6553 (4)	0.0505 (16)
C24	0.4879 (17)	0.1254 (7)	0.7329 (6)	0.0526 (19)
H24	0.3486	0.0843	0.7661	0.063*
C25	0.5981 (16)	0.2594 (6)	0.7660 (5)	0.0470 (17)
H25	0.5369	0.3086	0.8205	0.056*
C26	0.7973 (14)	0.3177 (6)	0.7173 (5)	0.0446 (17)
H26	0.8772	0.4089	0.7381	0.054*

	U11	U22	U33	U12	U13	U23
O1	0.045 (2)	0.027 (2)	0.054 (3)	0.0010 (19)	−0.005 (2)	0.001 (2)
O2	0.095 (4)	0.041 (3)	0.047 (3)	0.020 (3)	−0.005 (3)	−0.001 (2)
O3	0.036 (2)	0.035 (2)	0.043 (3)	−0.0023 (18)	0.005 (2)	0.004 (2)
O4	0.051 (3)	0.032 (3)	0.066 (4)	−0.004 (2)	0.006 (2)	0.003 (2)
C1	0.043 (3)	0.033 (4)	0.048 (5)	0.002 (3)	0.003 (3)	0.008 (3)
C2	0.044 (3)	0.033 (3)	0.053 (4)	0.006 (3)	0.006 (3)	0.014 (3)
C3	0.037 (3)	0.031 (3)	0.056 (4)	−0.008 (3)	−0.001 (3)	0.009 (3)
C4	0.041 (3)	0.040 (4)	0.054 (5)	0.002 (3)	0.015 (3)	0.020 (3)
C5	0.034 (3)	0.027 (3)	0.062 (5)	0.002 (3)	−0.001 (3)	0.002 (3)
C11	0.046 (3)	0.025 (3)	0.046 (4)	0.004 (3)	0.005 (3)	−0.002 (3)
C12	0.053 (4)	0.027 (3)	0.048 (5)	0.007 (3)	0.003 (3)	0.001 (3)
N13	0.072 (4)	0.039 (3)	0.051 (4)	0.013 (3)	−0.006 (3)	0.003 (3)
C14	0.057 (4)	0.041 (4)	0.057 (5)	0.012 (3)	−0.009 (4)	0.008 (4)
C15	0.059 (4)	0.043 (4)	0.049 (5)	0.008 (3)	0.007 (4)	−0.010 (3)
C16	0.066 (4)	0.030 (3)	0.051 (5)	0.006 (3)	0.009 (4)	0.001 (3)
C21	0.031 (3)	0.029 (3)	0.044 (4)	0.001 (2)	−0.007 (3)	−0.002 (3)
C22	0.045 (3)	0.024 (3)	0.063 (5)	0.001 (3)	0.003 (3)	0.003 (3)
N23	0.054 (3)	0.041 (3)	0.048 (4)	−0.002 (3)	0.004 (3)	0.008 (3)
C24	0.058 (4)	0.040 (4)	0.055 (5)	0.004 (3)	0.011 (4)	0.010 (4)
C25	0.050 (4)	0.034 (3)	0.047 (4)	0.006 (3)	−0.002 (3)	−0.002 (3)
C26	0.042 (3)	0.028 (3)	0.051 (5)	0.004 (3)	0.000 (3)	−0.008 (3)

O1—C1	1.353 (8)	C12—N13	1.329 (10)
O1—C2	1.472 (8)	C12—H12	0.9500
O2—C1	1.194 (8)	N13—C14	1.353 (10)
O3—C5	1.340 (8)	C14—C15	1.402 (10)
O3—C4	1.452 (7)	C14—H14	0.9500
O4—C5	1.193 (8)	C15—C16	1.349 (12)
C1—C11	1.475 (10)	C15—H15	0.9500
C2—C3	1.537 (9)	C16—H16	0.9500
C2—H2A	0.9900	C21—C22	1.379 (8)
C2—H2B	0.9900	C21—C26	1.384 (9)
C3—C4	1.528 (10)	C22—N23	1.328 (9)
C3—H3A	0.9900	C22—H22	0.9500
C3—H3B	0.9900	N23—C24	1.364 (10)
C4—H4A	0.9900	C24—C25	1.393 (9)
C4—H4B	0.9900	C24—H24	0.9500
C5—C21	1.504 (10)	C25—C26	1.368 (10)
C11—C16	1.389 (10)	C25—H25	0.9500
C11—C12	1.400 (8)	C26—H26	0.9500
C1—O1—C2	114.8 (5)	N13—C12—C11	123.2 (7)
C5—O3—C4	116.2 (5)	N13—C12—H12	118.4
O2—C1—O1	122.4 (6)	C11—C12—H12	118.4
O2—C1—C11	125.2 (6)	C12—N13—C14	118.4 (7)
O1—C1—C11	112.4 (6)	N13—C14—C15	121.1 (7)
O1—C2—C3	105.9 (5)	N13—C14—H14	119.5
O1—C2—H2A	110.6	C15—C14—H14	119.5
C3—C2—H2A	110.6	C16—C15—C14	119.9 (7)
O1—C2—H2B	110.6	C16—C15—H15	120.0
C3—C2—H2B	110.6	C14—C15—H15	120.0
H2A—C2—H2B	108.7	C15—C16—C11	119.8 (7)
C4—C3—C2	109.8 (6)	C15—C16—H16	120.1
C4—C3—H3A	109.7	C11—C16—H16	120.1
C2—C3—H3A	109.7	C22—C21—C26	117.6 (7)
C4—C3—H3B	109.7	C22—C21—C5	123.1 (6)
C2—C3—H3B	109.7	C26—C21—C5	119.3 (6)
H3A—C3—H3B	108.2	N23—C22—C21	125.0 (7)
O3—C4—C3	111.0 (5)	N23—C22—H22	117.5
O3—C4—H4A	109.4	C21—C22—H22	117.5
C3—C4—H4A	109.4	C22—N23—C24	115.8 (6)
O3—C4—H4B	109.4	N23—C24—C25	123.6 (7)
C3—C4—H4B	109.4	N23—C24—H24	118.2
H4A—C4—H4B	108.0	C25—C24—H24	118.2
O4—C5—O3	124.4 (6)	C26—C25—C24	117.7 (7)
O4—C5—C21	123.4 (7)	C26—C25—H25	121.2
O3—C5—C21	112.2 (5)	C24—C25—H25	121.2
C16—C11—C12	117.6 (7)	C25—C26—C21	120.3 (6)
C16—C11—C1	118.2 (6)	C25—C26—H26	119.8
C12—C11—C1	124.1 (6)	C21—C26—H26	119.8
C2—O1—C1—O2	−3.1 (9)	N13—C14—C15—C16	1.9 (12)
C2—O1—C1—C11	177.9 (5)	C14—C15—C16—C11	−2.9 (11)
C1—O1—C2—C3	171.4 (5)	C12—C11—C16—C15	3.2 (10)
O1—C2—C3—C4	173.9 (5)	C1—C11—C16—C15	−178.9 (7)
C5—O3—C4—C3	−84.3 (7)	O4—C5—C21—C22	−179.8 (7)
C2—C3—C4—O3	−70.1 (7)	O3—C5—C21—C22	−1.8 (9)
C4—O3—C5—O4	−1.7 (10)	O4—C5—C21—C26	0.8 (10)
C4—O3—C5—C21	−179.6 (6)	O3—C5—C21—C26	178.7 (6)
O2—C1—C11—C16	0.4 (11)	C26—C21—C22—N23	−0.4 (11)
O1—C1—C11—C16	179.4 (6)	C5—C21—C22—N23	−179.9 (7)
O2—C1—C11—C12	178.2 (7)	C21—C22—N23—C24	0.9 (11)
O1—C1—C11—C12	−2.8 (9)	C22—N23—C24—C25	−0.9 (11)
C16—C11—C12—N13	−2.5 (10)	N23—C24—C25—C26	0.3 (12)
C1—C11—C12—N13	179.7 (7)	C24—C25—C26—C21	0.2 (10)
C11—C12—N13—C14	1.4 (11)	C22—C21—C26—C25	−0.2 (10)
C12—N13—C14—C15	−1.1 (11)	C5—C21—C26—C25	179.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.99	2.49	3.341 (8)	144
C16—H16···O2ii	0.95	2.45	3.198 (10)	136
C24—H24···O2iii	0.95	2.45	3.218 (10)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.99	2.49	3.341 (8)	144
C16—H16⋯O2ii	0.95	2.45	3.198 (10)	136
C24—H24⋯O2iii	0.95	2.45	3.218 (10)	138

Symmetry codes: (i) ; (ii) ; (iii) .