A monoclinic modification of propane-1,3-diyl bis-(pyridine-3-carboxyl-ate).

In the title compound, C(15)H(14)N(2)O(4), (I), the mol-ecule lies on a twofold rotation axis which passes through the central C atom of the aliphatic chain, giving one half-mol-ecule per asymmetric unit. The structure is a monoclinic polymorph of the triclinic structure previously reported [Brito, Vallejos, Bolte & López-Rodríguez (2010). Acta Cryst. E66, o792], (II). The most obvious difference between them is the O/C/C/C-O/C/C/C torsion angle [58.2 (7)° in (I) and 173.4 (3)/70.2 (3)° in (II) for GG and TG conformations, respectively]. Another important difference is observed in the dihedral angle between the planes of the aromatic rings [86.49 (7)° for (I) and 76.4 (3)° for (II)]. The crystal structure features a weak π-π inter-action [centroid-centroid distance = 4.1397 (10)Å]; this latter kind of inter-action is not evident in the triclinic polymorph.

Related literature

For conformation definitions, see: Carlucci et al. (2002 ▶). For the structure of the triclinic polymorph, see: Brito et al. (2010a ▶). For the synthesis and structural characterization of coordination polymers, see: Brito et al. (2010b ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 24.414 (3) Å

b = 4.8328 (4) Å

c = 11.5667 (14) Å

β = 100.671 (10)°

V = 1341.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.35 × 0.33 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer

3193 measured reflections

1249 independent reflections

939 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 0.92

1249 reflections

97 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 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 in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054309/om2394sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054309/om2394Isup2.hkl

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.418 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2928 reflections
a = 24.414 (3) Å	θ = 3.4–25.9°
b = 4.8328 (4) Å	µ = 0.11 mm−1
c = 11.5667 (14) Å	T = 173 K
β = 100.671 (10)°	Block, colourless
V = 1341.1 (3) Å3	0.35 × 0.33 × 0.13 mm
Z = 4

Stoe IPDS II two-circle diffractometer	939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 25.6°, θmin = 3.4°
ω scans	h = −29→29
3193 measured reflections	k = −5→5
1249 independent reflections	l = −14→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0497P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
1249 reflections	Δρmax = 0.17 e Å−3
97 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0099 (13)

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	0.57094 (4)	0.5968 (2)	0.53846 (8)	0.0343 (3)
C1	0.58554 (6)	0.5710 (3)	0.44442 (11)	0.0250 (3)
O2	0.56326 (4)	0.7135 (2)	0.34794 (7)	0.0273 (3)
C3	0.51676 (6)	0.8926 (3)	0.36128 (11)	0.0272 (3)
H3A	0.5280	1.0184	0.4291	0.033*
H3B	0.4849	0.7795	0.3759	0.033*
C4	0.5000	1.0583 (4)	0.2500	0.0266 (5)
H4A	0.4679	1.1804	0.2599	0.032*
C11	0.62930 (6)	0.3744 (3)	0.42290 (11)	0.0254 (3)
C12	0.65354 (6)	0.2013 (3)	0.51425 (12)	0.0299 (4)
H12	0.6415	0.2180	0.5875	0.036*
N13	0.69262 (5)	0.0130 (3)	0.50556 (10)	0.0342 (3)
C14	0.70870 (6)	−0.0051 (3)	0.40112 (12)	0.0324 (4)
H14	0.7368	−0.1360	0.3930	0.039*
C15	0.68699 (6)	0.1548 (3)	0.30476 (12)	0.0317 (4)
H15	0.6998	0.1327	0.2325	0.038*
C16	0.64628 (6)	0.3481 (3)	0.31495 (11)	0.0290 (3)
H16	0.6303	0.4601	0.2499	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0395 (6)	0.0414 (6)	0.0238 (5)	0.0043 (5)	0.0102 (4)	0.0026 (4)
C1	0.0281 (8)	0.0259 (7)	0.0199 (6)	−0.0060 (6)	0.0013 (6)	0.0007 (5)
O2	0.0313 (6)	0.0290 (5)	0.0220 (5)	0.0045 (4)	0.0062 (4)	0.0017 (4)
C3	0.0274 (8)	0.0293 (8)	0.0260 (7)	0.0015 (6)	0.0080 (6)	−0.0020 (6)
C4	0.0259 (11)	0.0260 (11)	0.0281 (9)	0.000	0.0057 (8)	0.000
C11	0.0268 (7)	0.0248 (7)	0.0238 (6)	−0.0053 (6)	0.0030 (6)	−0.0014 (5)
C12	0.0355 (9)	0.0308 (8)	0.0232 (6)	−0.0007 (7)	0.0049 (6)	−0.0009 (6)
N13	0.0378 (8)	0.0339 (7)	0.0303 (6)	0.0037 (6)	0.0045 (5)	0.0008 (5)
C14	0.0306 (9)	0.0315 (8)	0.0354 (8)	0.0008 (6)	0.0067 (6)	−0.0042 (6)
C15	0.0335 (8)	0.0346 (8)	0.0282 (7)	−0.0043 (7)	0.0091 (6)	−0.0037 (6)
C16	0.0321 (8)	0.0312 (8)	0.0231 (7)	−0.0052 (6)	0.0037 (6)	0.0009 (6)

O1—C1	1.2122 (14)	C11—C16	1.3925 (16)
C1—O2	1.3381 (16)	C12—N13	1.3355 (19)
C1—C11	1.4849 (19)	C12—H12	0.9500
O2—C3	1.4585 (16)	N13—C14	1.3405 (17)
C3—C4	1.5069 (17)	C14—C15	1.379 (2)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—C16	1.385 (2)
C4—C3i	1.5069 (17)	C15—H15	0.9500
C4—H4A	1.0042	C16—H16	0.9500
C11—C12	1.391 (2)
O1—C1—O2	123.62 (13)	C16—C11—C1	123.47 (12)
O1—C1—C11	123.82 (12)	N13—C12—C11	124.20 (12)
O2—C1—C11	112.54 (10)	N13—C12—H12	117.9
C1—O2—C3	114.92 (9)	C11—C12—H12	117.9
O2—C3—C4	108.59 (9)	C12—N13—C14	116.40 (13)
O2—C3—H3A	110.0	N13—C14—C15	123.98 (14)
C4—C3—H3A	110.0	N13—C14—H14	118.0
O2—C3—H3B	110.0	C15—C14—H14	118.0
C4—C3—H3B	110.0	C14—C15—C16	118.94 (12)
H3A—C3—H3B	108.4	C14—C15—H15	120.5
C3i—C4—C3	115.77 (17)	C16—C15—H15	120.5
C3i—C4—H4A	108.4	C15—C16—C11	118.38 (13)
C3—C4—H4A	108.0	C15—C16—H16	120.8
C12—C11—C16	118.09 (13)	C11—C16—H16	120.8
C12—C11—C1	118.41 (11)
O1—C1—O2—C3	−3.94 (19)	C16—C11—C12—N13	0.8 (2)
C11—C1—O2—C3	174.99 (11)	C1—C11—C12—N13	178.94 (14)
C1—O2—C3—C4	174.58 (12)	C11—C12—N13—C14	0.1 (2)
O2—C3—C4—C3i	58.11 (8)	C12—N13—C14—C15	−0.7 (2)
O1—C1—C11—C12	2.7 (2)	N13—C14—C15—C16	0.4 (2)
O2—C1—C11—C12	−176.23 (13)	C14—C15—C16—C11	0.5 (2)
O1—C1—C11—C16	−179.25 (13)	C12—C11—C16—C15	−1.1 (2)
O2—C1—C11—C16	1.83 (19)	C1—C11—C16—C15	−179.13 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.95	2.51	2.8298 (18)	100