4-[5-(4-Pyrid-yl)-1,3,4-oxadiazol-2-yl]pyridine N-oxide-isophthalic acid (1/1).

The title compound, C(12)H(8)N(4)O(2)·C(8)H(6)O(4), was synthesized from 4-[5-(4-pyrid-yl)-1,3,4-oxadiazol-2-yl]pyridine N-oxide and isophthalic acid. The two mol-ecules are linked through O-H⋯O and O-H⋯N hydrogen bonds. Weak intra-molecular π-π inter-actions between the two hydrogen-bonded chains result in the formation a one-dimensional supra-molecular curved tape (the face-to-face distance between the pyridine N-oxide ring and the benzene ring is 3.7 Å).

Related literature

For related literature, see: Beckmann & Jänicke (2006 ▶); Dong et al. (2003 ▶); Du et al. (2006 ▶); Hunter (1994 ▶); Kitagawa et al. (2004 ▶); Long et al. (2004 ▶); Lu et al. (1997 ▶); Ma et al. (2005 ▶); Ren et al. (1995 ▶); Tan et al. (2006 ▶).

Experimental

Crystal data

C12H8N4O2·C8H6O4

M = 406.35

Triclinic,

a = 7.0993 (18) Å

b = 7.1770 (19) Å

c = 19.823 (5) Å

α = 93.003 (4)°

β = 98.481 (3)°

γ = 112.745 (4)°

V = 914.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.30 × 0.15 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

4661 measured reflections

3189 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.132

S = 0.98

3189 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012622/bv2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012622/bv2095Isup2.hkl

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

C12H8N4O2·C8H6O4	Z = 2
Mr = 406.35	F000 = 420
Triclinic, P1	Dx = 1.475 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.0993 (18) Å	Cell parameters from 893 reflections
b = 7.1770 (19) Å	θ = 3.2–21.1º
c = 19.823 (5) Å	µ = 0.11 mm−1
α = 93.003 (4)º	T = 298 (2) K
β = 98.481 (3)º	Bar, colourless
γ = 112.745 (4)º	0.30 × 0.15 × 0.06 mm
V = 914.6 (4) Å3

Bruker SMART APEX diffractometer	1972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Monochromator: graphite	θmax = 25.0º
T = 298(2) K	θmin = 3.1º
φ and ω scans	h = −8→8
Absorption correction: none	k = −8→8
4661 measured reflections	l = −17→23
3189 independent reflections

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0637P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3189 reflections	Δρmax = 0.30 e Å−3
272 parameters	Δρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.7708 (3)	0.9021 (3)	0.64281 (9)	0.0693 (6)
O2	1.0221 (3)	0.8709 (4)	0.59557 (10)	0.0861 (7)
O5	−0.2941 (3)	0.2221 (4)	−0.02763 (9)	0.0882 (8)
O3	0.8643 (3)	1.0843 (3)	0.88695 (9)	0.0738 (6)
H3	0.8309	1.1276	0.9203	0.111*
O4	1.1774 (3)	1.2181 (3)	0.95238 (9)	0.0726 (6)
C1	−0.4071 (4)	0.2792 (4)	0.06980 (13)	0.0592 (8)
H1A	−0.5408	0.2374	0.0446	0.071*
C2	−0.3697 (4)	0.3405 (4)	0.13821 (12)	0.0528 (7)
H2	−0.4781	0.3399	0.1595	0.063*
C3	−0.1721 (4)	0.4035 (4)	0.17649 (11)	0.0427 (6)
C4	−0.0155 (4)	0.4016 (4)	0.14322 (12)	0.0515 (7)
H4	0.1189	0.4429	0.1678	0.062*
C5	−0.0572 (4)	0.3385 (4)	0.07365 (12)	0.0558 (7)
H5A	0.0489	0.3375	0.0513	0.067*
C6	−0.1345 (4)	0.4706 (4)	0.24973 (12)	0.0436 (6)
C7	0.0337 (4)	0.5784 (4)	0.35129 (11)	0.0431 (6)
C8	0.2083 (4)	0.6463 (4)	0.40831 (11)	0.0415 (6)
C9	0.1803 (4)	0.7064 (4)	0.47216 (12)	0.0496 (7)
H9	0.0533	0.7076	0.4782	0.059*
C10	0.3421 (4)	0.7639 (4)	0.52633 (12)	0.0520 (7)
H10	0.3205	0.8000	0.5694	0.062*
C11	0.5555 (4)	0.7154 (4)	0.45907 (13)	0.0551 (7)
H11	0.6856	0.7205	0.4542	0.066*
C12	0.4001 (4)	0.6505 (4)	0.40169 (12)	0.0490 (7)
H12	0.4245	0.6105	0.3596	0.059*
C13	0.9602 (4)	0.9161 (4)	0.64414 (14)	0.0521 (7)
C14	1.0945 (4)	0.9948 (4)	0.71368 (11)	0.0453 (6)
C15	1.0149 (4)	1.0271 (4)	0.77116 (12)	0.0451 (6)
H15	0.8738	0.9975	0.7670	0.054*
C16	1.1455 (4)	1.1037 (4)	0.83507 (11)	0.0436 (6)
C17	1.3553 (4)	1.1470 (4)	0.84013 (13)	0.0533 (7)
H17	1.4443	1.1995	0.8822	0.064*
C18	1.4324 (4)	1.1130 (4)	0.78334 (13)	0.0577 (8)
H18	1.5734	1.1419	0.7874	0.069*
C19	1.3043 (4)	1.0369 (4)	0.72065 (13)	0.0542 (7)
H19	1.3586	1.0134	0.6827	0.065*
C20	1.0666 (4)	1.1418 (4)	0.89757 (13)	0.0509 (7)
N1	−0.2515 (3)	0.2788 (3)	0.03830 (10)	0.0569 (6)
N2	−0.2670 (3)	0.4826 (3)	0.28576 (10)	0.0511 (6)
N3	−0.1552 (3)	0.5550 (3)	0.35274 (10)	0.0529 (6)
N4	0.5295 (3)	0.7709 (3)	0.52071 (10)	0.0525 (6)
H1	0.7016	0.8526	0.6043	0.079*
O6	0.0597 (2)	0.5275 (2)	0.28698 (7)	0.0451 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0608 (14)	0.0982 (17)	0.0411 (11)	0.0313 (12)	−0.0073 (9)	−0.0095 (10)
O2	0.0854 (16)	0.128 (2)	0.0449 (12)	0.0492 (15)	0.0062 (11)	−0.0239 (12)
O5	0.0759 (15)	0.157 (2)	0.0339 (12)	0.0592 (15)	−0.0082 (10)	−0.0223 (12)
O3	0.0545 (13)	0.1118 (18)	0.0450 (12)	0.0277 (12)	0.0025 (9)	−0.0144 (11)
O4	0.0630 (13)	0.1144 (18)	0.0341 (11)	0.0374 (12)	−0.0070 (9)	−0.0135 (11)
C1	0.0494 (17)	0.077 (2)	0.0459 (17)	0.0259 (15)	−0.0048 (13)	−0.0079 (14)
C2	0.0514 (17)	0.0658 (19)	0.0379 (16)	0.0239 (14)	0.0000 (12)	−0.0024 (13)
C3	0.0490 (16)	0.0424 (16)	0.0352 (14)	0.0190 (12)	0.0020 (12)	0.0006 (11)
C4	0.0498 (17)	0.0596 (19)	0.0377 (16)	0.0182 (14)	−0.0013 (12)	−0.0006 (12)
C5	0.0523 (18)	0.075 (2)	0.0405 (16)	0.0282 (15)	0.0051 (13)	0.0002 (14)
C6	0.0501 (17)	0.0421 (16)	0.0331 (14)	0.0167 (13)	−0.0027 (12)	0.0002 (11)
C7	0.0534 (17)	0.0443 (16)	0.0326 (15)	0.0210 (13)	0.0079 (12)	0.0010 (11)
C8	0.0474 (16)	0.0436 (16)	0.0313 (14)	0.0182 (12)	0.0019 (11)	0.0009 (11)
C9	0.0487 (16)	0.0590 (18)	0.0375 (15)	0.0193 (14)	0.0060 (12)	−0.0018 (12)
C10	0.0591 (19)	0.0614 (19)	0.0319 (15)	0.0225 (15)	0.0052 (13)	−0.0025 (12)
C11	0.0491 (17)	0.066 (2)	0.0508 (18)	0.0258 (15)	0.0033 (14)	0.0032 (14)
C12	0.0551 (18)	0.0575 (18)	0.0338 (15)	0.0228 (14)	0.0073 (13)	−0.0006 (12)
C13	0.0625 (19)	0.0471 (18)	0.0468 (18)	0.0236 (14)	0.0068 (14)	0.0024 (13)
C14	0.0574 (17)	0.0467 (17)	0.0315 (14)	0.0233 (13)	0.0020 (12)	−0.0004 (11)
C15	0.0472 (15)	0.0468 (16)	0.0417 (15)	0.0221 (13)	0.0003 (12)	0.0039 (12)
C16	0.0492 (16)	0.0482 (16)	0.0329 (14)	0.0220 (13)	−0.0005 (12)	0.0029 (11)
C17	0.0537 (18)	0.0604 (19)	0.0428 (16)	0.0251 (15)	−0.0042 (13)	−0.0001 (13)
C18	0.0508 (17)	0.073 (2)	0.0485 (18)	0.0270 (16)	0.0037 (14)	0.0004 (15)
C19	0.0609 (19)	0.0605 (19)	0.0458 (17)	0.0285 (15)	0.0126 (14)	0.0029 (13)
C20	0.0509 (18)	0.0600 (19)	0.0408 (16)	0.0251 (14)	−0.0007 (13)	0.0014 (13)
N1	0.0585 (16)	0.0779 (18)	0.0301 (13)	0.0295 (13)	−0.0054 (11)	−0.0088 (11)
N2	0.0505 (14)	0.0635 (16)	0.0366 (13)	0.0230 (12)	0.0021 (10)	−0.0024 (10)
N3	0.0525 (15)	0.0684 (16)	0.0351 (13)	0.0244 (12)	0.0016 (10)	−0.0013 (10)
N4	0.0582 (15)	0.0540 (15)	0.0382 (13)	0.0189 (12)	−0.0012 (11)	0.0011 (10)
O6	0.0486 (11)	0.0548 (11)	0.0293 (9)	0.0211 (9)	0.0009 (8)	−0.0035 (7)

O1—C13	1.306 (3)	C8—C12	1.377 (3)
O1—H1	0.8221	C8—C9	1.382 (3)
O2—C13	1.195 (3)	C9—C10	1.366 (3)
O5—N1	1.303 (2)	C9—H9	0.9300
O3—C20	1.312 (3)	C10—N4	1.333 (3)
O3—H3	0.8200	C10—H10	0.9300
O4—C20	1.205 (3)	C11—N4	1.326 (3)
C1—N1	1.347 (3)	C11—C12	1.380 (3)
C1—C2	1.358 (3)	C11—H11	0.9300
C1—H1A	0.9300	C12—H12	0.9300
C2—C3	1.381 (3)	C13—C14	1.497 (3)
C2—H2	0.9300	C14—C19	1.384 (3)
C3—C4	1.378 (3)	C14—C15	1.391 (3)
C3—C6	1.457 (3)	C15—C16	1.398 (3)
C4—C5	1.380 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.385 (3)
C5—N1	1.343 (3)	C16—C20	1.487 (3)
C5—H5A	0.9300	C17—C18	1.372 (3)
C6—N2	1.287 (3)	C17—H17	0.9300
C6—O6	1.358 (3)	C18—C19	1.372 (3)
C7—N3	1.290 (3)	C18—H18	0.9300
C7—O6	1.366 (3)	C19—H19	0.9300
C7—C8	1.454 (3)	N2—N3	1.400 (3)
C13—O1—H1	109.3	C8—C12—C11	118.4 (2)
C20—O3—H3	109.5	C8—C12—H12	120.8
N1—C1—C2	120.3 (2)	C11—C12—H12	120.8
N1—C1—H1A	119.8	O2—C13—O1	124.3 (3)
C2—C1—H1A	119.8	O2—C13—C14	122.8 (3)
C1—C2—C3	120.7 (2)	O1—C13—C14	112.8 (2)
C1—C2—H2	119.7	C19—C14—C15	119.2 (2)
C3—C2—H2	119.7	C19—C14—C13	118.7 (2)
C4—C3—C2	118.0 (2)	C15—C14—C13	122.0 (2)
C4—C3—C6	122.1 (2)	C14—C15—C16	120.4 (2)
C2—C3—C6	119.9 (2)	C14—C15—H15	119.8
C3—C4—C5	120.3 (2)	C16—C15—H15	119.8
C3—C4—H4	119.8	C17—C16—C15	118.9 (2)
C5—C4—H4	119.8	C17—C16—C20	119.1 (2)
N1—C5—C4	119.7 (2)	C15—C16—C20	122.0 (2)
N1—C5—H5A	120.1	C18—C17—C16	120.3 (2)
C4—C5—H5A	120.1	C18—C17—H17	119.8
N2—C6—O6	113.3 (2)	C16—C17—H17	119.8
N2—C6—C3	127.5 (2)	C19—C18—C17	120.8 (3)
O6—C6—C3	119.1 (2)	C19—C18—H18	119.6
N3—C7—O6	112.1 (2)	C17—C18—H18	119.6
N3—C7—C8	127.9 (2)	C18—C19—C14	120.2 (2)
O6—C7—C8	120.0 (2)	C18—C19—H19	119.9
C12—C8—C9	118.4 (2)	C14—C19—H19	119.9
C12—C8—C7	122.7 (2)	O4—C20—O3	123.4 (2)
C9—C8—C7	118.8 (2)	O4—C20—C16	123.4 (2)
C10—C9—C8	119.0 (2)	O3—C20—C16	113.2 (2)
C10—C9—H9	120.5	O5—N1—C5	120.9 (2)
C8—C9—H9	120.5	O5—N1—C1	118.2 (2)
N4—C10—C9	123.4 (2)	C5—N1—C1	120.9 (2)
N4—C10—H10	118.3	C6—N2—N3	105.6 (2)
C9—C10—H10	118.3	C7—N3—N2	106.81 (19)
N4—C11—C12	123.7 (2)	C11—N4—C10	117.1 (2)
N4—C11—H11	118.2	C6—O6—C7	102.14 (18)
C12—C11—H11	118.2
N1—C1—C2—C3	0.2 (4)	C14—C15—C16—C20	179.5 (2)
C1—C2—C3—C4	−0.2 (4)	C15—C16—C17—C18	−0.7 (4)
C1—C2—C3—C6	179.4 (2)	C20—C16—C17—C18	179.9 (2)
C2—C3—C4—C5	0.1 (4)	C16—C17—C18—C19	0.4 (4)
C6—C3—C4—C5	−179.5 (2)	C17—C18—C19—C14	0.6 (4)
C3—C4—C5—N1	0.0 (4)	C15—C14—C19—C18	−1.2 (4)
C4—C3—C6—N2	178.5 (3)	C13—C14—C19—C18	178.7 (2)
C2—C3—C6—N2	−1.1 (4)	C17—C16—C20—O4	3.7 (4)
C4—C3—C6—O6	−2.0 (4)	C15—C16—C20—O4	−175.7 (3)
C2—C3—C6—O6	178.4 (2)	C17—C16—C20—O3	−176.5 (2)
N3—C7—C8—C12	174.8 (2)	C15—C16—C20—O3	4.1 (4)
O6—C7—C8—C12	−4.2 (4)	C4—C5—N1—O5	178.7 (2)
N3—C7—C8—C9	−4.2 (4)	C4—C5—N1—C1	0.0 (4)
O6—C7—C8—C9	176.9 (2)	C2—C1—N1—O5	−178.8 (2)
C12—C8—C9—C10	−1.1 (4)	C2—C1—N1—C5	0.0 (4)
C7—C8—C9—C10	177.9 (2)	O6—C6—N2—N3	0.5 (3)
C8—C9—C10—N4	2.0 (4)	C3—C6—N2—N3	−179.9 (2)
C9—C8—C12—C11	−0.3 (4)	O6—C7—N3—N2	0.4 (3)
C7—C8—C12—C11	−179.3 (2)	C8—C7—N3—N2	−178.6 (2)
N4—C11—C12—C8	1.2 (4)	C6—N2—N3—C7	−0.5 (3)
O2—C13—C14—C19	6.8 (4)	C12—C11—N4—C10	−0.5 (4)
O1—C13—C14—C19	−173.4 (2)	C9—C10—N4—C11	−1.1 (4)
O2—C13—C14—C15	−173.3 (3)	N2—C6—O6—C7	−0.3 (3)
O1—C13—C14—C15	6.5 (4)	C3—C6—O6—C7	−179.9 (2)
C19—C14—C15—C16	0.9 (4)	N3—C7—O6—C6	0.0 (3)
C13—C14—C15—C16	−179.0 (2)	C8—C7—O6—C6	179.0 (2)
C14—C15—C16—C17	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4	0.82	1.82	2.640 (2)	171
O3—H3···O5i	0.82	1.72	2.521 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4	0.82	1.82	2.640 (2)	171
O3—H3⋯O5i	0.82	1.72	2.521 (3)	163

Symmetry code: (i) .