4-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridinium benzoate.

In the title compound, C(12)H(9)N(4)O(+)·C(7)H(5)O(2) (-), π-π stacking inter-actions [centroid-centroid distance = 3.6275 (14)  Å] stabilize the crystal structure. The dihedral angles between the central ring and the terminal rings are 3.27 (12) and 10.30 (13)°.

Related literature

For background to the development of ferroelectric compounds, see: Haertling et al. (1999 ▶); Homes et al. (2001 ▶). For the synthesis of a variety of compounds with potential piezoelectric and ferroelectric properties, see: Ye et al. (2006 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C12H9N4O+·C7H5O2 −

M = 346.34

Monoclinic,

a = 20.459 (4) Å

b = 7.1958 (14) Å

c = 11.249 (2) Å

β = 90.53 (3)°

V = 1656.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.854, T max = 1.000

16725 measured reflections

3808 independent reflections

2248 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.171

S = 1.02

3808 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536811001358/jh2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001358/jh2244Isup2.hkl

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

C12H9N4O+·C7H5O2−	F(000) = 720
Mr = 346.34	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3808 reflections
a = 20.459 (4) Å	θ = 2.6–27.5°
b = 7.1958 (14) Å	µ = 0.10 mm−1
c = 11.249 (2) Å	T = 293 K
β = 90.53 (3)°	Prism, colourless
V = 1656.0 (5) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	3808 independent reflections
Radiation source: fine-focus sealed tube	2248 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −26→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.854, Tmax = 1.000	l = −14→14
16725 measured 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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.079P)2 + 0.2253P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3808 reflections	Δρmax = 0.27 e Å−3
236 parameters	Δρmin = −0.28 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: 0.0130 (18)

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
C1	0.11341 (11)	0.8827 (3)	0.1577 (2)	0.0468 (5)
C2	0.18546 (10)	0.8838 (3)	0.13768 (18)	0.0406 (5)
C3	0.22890 (10)	0.9438 (3)	0.22500 (19)	0.0453 (5)
H3	0.2133	0.9853	0.2977	0.054*
C4	0.29500 (11)	0.9420 (3)	0.2041 (2)	0.0529 (6)
H4	0.3240	0.9831	0.2626	0.064*
C5	0.31834 (12)	0.8796 (3)	0.0974 (2)	0.0602 (7)
H5	0.3631	0.8780	0.0839	0.072*
C6	0.27599 (13)	0.8197 (3)	0.0105 (2)	0.0625 (7)
H6	0.2921	0.7771	−0.0615	0.075*
C7	0.20926 (12)	0.8224 (3)	0.02954 (19)	0.0510 (6)
H7	0.1805	0.7831	−0.0299	0.061*
C8	0.04872 (11)	0.3443 (3)	0.0797 (2)	0.0566 (6)
H8	0.0171	0.3137	0.0231	0.068*
C9	0.11320 (10)	0.3396 (3)	0.0482 (2)	0.0494 (6)
H9	0.1251	0.3092	−0.0290	0.059*
C10	0.16028 (10)	0.3805 (3)	0.13262 (18)	0.0398 (5)
C11	0.14062 (10)	0.4269 (3)	0.2463 (2)	0.0471 (6)
H11	0.1712	0.4538	0.3054	0.057*
C12	0.07469 (11)	0.4324 (3)	0.2698 (2)	0.0545 (6)
H12	0.0612	0.4662	0.3455	0.065*
C13	0.22928 (10)	0.3753 (3)	0.10114 (18)	0.0391 (5)
C14	0.33195 (10)	0.3951 (3)	0.12671 (18)	0.0401 (5)
C15	0.50844 (12)	0.4366 (4)	0.2044 (3)	0.0739 (8)
H15	0.5481	0.4410	0.1649	0.089*
C16	0.45215 (11)	0.4228 (4)	0.1364 (2)	0.0634 (7)
H16	0.4541	0.4184	0.0539	0.076*
C17	0.39284 (10)	0.4158 (3)	0.19378 (19)	0.0430 (5)
C18	0.39322 (11)	0.4232 (3)	0.3154 (2)	0.0572 (7)
H18	0.3542	0.4195	0.3572	0.069*
C19	0.45201 (13)	0.4362 (4)	0.3748 (2)	0.0721 (8)
H19	0.4513	0.4400	0.4575	0.086*
N1	0.02979 (9)	0.3912 (3)	0.1885 (2)	0.0577 (6)
H1A	−0.0111	0.3947	0.2058	0.069*
N2	0.25515 (9)	0.3426 (3)	−0.00105 (16)	0.0489 (5)
N3	0.32318 (9)	0.3568 (3)	0.01599 (16)	0.0493 (5)
N4	0.50991 (10)	0.4439 (3)	0.3221 (2)	0.0726 (7)
O1	0.07395 (8)	0.8483 (3)	0.08005 (16)	0.0711 (5)
O2	0.09672 (7)	0.9211 (2)	0.26772 (15)	0.0629 (5)
O3	0.27482 (6)	0.40949 (19)	0.18688 (12)	0.0406 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (13)	0.0411 (12)	0.0553 (15)	−0.0043 (10)	−0.0113 (11)	−0.0002 (10)
C2	0.0444 (12)	0.0344 (11)	0.0429 (12)	−0.0029 (9)	−0.0044 (9)	0.0034 (9)
C3	0.0413 (12)	0.0522 (13)	0.0422 (12)	−0.0002 (10)	−0.0042 (9)	0.0024 (10)
C4	0.0401 (13)	0.0595 (15)	0.0591 (15)	−0.0068 (11)	−0.0098 (11)	0.0076 (11)
C5	0.0448 (14)	0.0601 (16)	0.0758 (18)	−0.0034 (12)	0.0100 (13)	0.0098 (13)
C6	0.0682 (18)	0.0578 (16)	0.0618 (16)	−0.0058 (13)	0.0178 (13)	−0.0026 (12)
C7	0.0615 (15)	0.0460 (13)	0.0456 (13)	−0.0091 (11)	−0.0039 (11)	0.0015 (10)
C8	0.0395 (13)	0.0617 (15)	0.0682 (17)	−0.0021 (11)	−0.0132 (12)	−0.0008 (12)
C9	0.0428 (13)	0.0561 (14)	0.0492 (13)	0.0003 (10)	−0.0092 (10)	−0.0042 (11)
C10	0.0370 (11)	0.0373 (11)	0.0451 (12)	−0.0022 (9)	−0.0050 (9)	0.0046 (9)
C11	0.0388 (12)	0.0560 (14)	0.0464 (13)	−0.0034 (10)	−0.0063 (10)	0.0027 (10)
C12	0.0451 (13)	0.0617 (16)	0.0569 (15)	0.0032 (11)	0.0027 (11)	0.0064 (11)
C13	0.0407 (11)	0.0394 (12)	0.0372 (11)	−0.0030 (9)	−0.0074 (9)	−0.0002 (9)
C14	0.0353 (11)	0.0432 (12)	0.0419 (12)	−0.0020 (9)	0.0049 (9)	0.0026 (9)
C15	0.0372 (14)	0.103 (2)	0.081 (2)	−0.0078 (14)	0.0073 (13)	−0.0025 (16)
C16	0.0410 (13)	0.092 (2)	0.0574 (15)	−0.0070 (13)	0.0037 (11)	0.0018 (13)
C17	0.0362 (11)	0.0467 (13)	0.0460 (13)	−0.0023 (9)	0.0008 (9)	0.0057 (9)
C18	0.0394 (13)	0.0816 (18)	0.0506 (14)	−0.0053 (12)	−0.0014 (11)	0.0011 (12)
C19	0.0539 (16)	0.104 (2)	0.0579 (16)	−0.0041 (15)	−0.0127 (13)	0.0004 (15)
N1	0.0328 (10)	0.0649 (13)	0.0754 (15)	0.0006 (9)	0.0003 (10)	0.0121 (11)
N2	0.0457 (11)	0.0590 (12)	0.0419 (11)	0.0019 (9)	−0.0016 (8)	−0.0020 (8)
N3	0.0417 (11)	0.0635 (12)	0.0427 (11)	0.0022 (9)	−0.0006 (8)	−0.0010 (9)
N4	0.0459 (13)	0.0927 (17)	0.0788 (17)	−0.0042 (11)	−0.0120 (11)	0.0011 (13)
O1	0.0483 (10)	0.0923 (14)	0.0722 (12)	−0.0078 (9)	−0.0216 (9)	−0.0066 (10)
O2	0.0431 (9)	0.0843 (13)	0.0613 (11)	−0.0048 (8)	0.0007 (8)	−0.0140 (9)
O3	0.0325 (8)	0.0515 (9)	0.0379 (8)	−0.0036 (6)	−0.0017 (6)	0.0002 (6)

C1—O1	1.210 (2)	C11—C12	1.377 (3)
C1—O2	1.316 (3)	C11—H11	0.9300
C1—C2	1.493 (3)	C12—N1	1.323 (3)
C2—C7	1.387 (3)	C12—H12	0.9300
C2—C3	1.387 (3)	C13—N2	1.292 (3)
C3—C4	1.375 (3)	C13—O3	1.357 (2)
C3—H3	0.9300	C14—N3	1.287 (3)
C4—C5	1.372 (3)	C14—O3	1.360 (2)
C4—H4	0.9300	C14—C17	1.458 (3)
C5—C6	1.370 (3)	C15—N4	1.324 (3)
C5—H5	0.9300	C15—C16	1.380 (3)
C6—C7	1.384 (3)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.381 (3)
C7—H7	0.9300	C16—H16	0.9300
C8—N1	1.332 (3)	C17—C18	1.369 (3)
C8—C9	1.369 (3)	C18—C19	1.374 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.378 (3)	C19—N4	1.331 (3)
C9—H9	0.9300	C19—H19	0.9300
C10—C11	1.385 (3)	N1—H1A	0.8600
C10—C13	1.459 (3)	N2—N3	1.407 (2)
O1—C1—O2	123.0 (2)	C10—C11—H11	120.7
O1—C1—C2	123.0 (2)	N1—C12—C11	122.4 (2)
O2—C1—C2	113.95 (18)	N1—C12—H12	118.8
C7—C2—C3	119.5 (2)	C11—C12—H12	118.8
C7—C2—C1	119.06 (19)	N2—C13—O3	112.41 (18)
C3—C2—C1	121.43 (19)	N2—C13—C10	128.76 (19)
C4—C3—C2	120.0 (2)	O3—C13—C10	118.84 (17)
C4—C3—H3	120.0	N3—C14—O3	112.67 (18)
C2—C3—H3	120.0	N3—C14—C17	129.31 (19)
C5—C4—C3	120.2 (2)	O3—C14—C17	117.96 (18)
C5—C4—H4	119.9	N4—C15—C16	124.6 (2)
C3—C4—H4	119.9	N4—C15—H15	117.7
C6—C5—C4	120.3 (2)	C16—C15—H15	117.7
C6—C5—H5	119.9	C15—C16—C17	118.4 (2)
C4—C5—H5	119.9	C15—C16—H16	120.8
C5—C6—C7	120.2 (2)	C17—C16—H16	120.8
C5—C6—H6	119.9	C18—C17—C16	118.0 (2)
C7—C6—H6	119.9	C18—C17—C14	121.20 (19)
C6—C7—C2	119.7 (2)	C16—C17—C14	120.8 (2)
C6—C7—H7	120.2	C17—C18—C19	119.1 (2)
C2—C7—H7	120.2	C17—C18—H18	120.5
N1—C8—C9	122.2 (2)	C19—C18—H18	120.5
N1—C8—H8	118.9	N4—C19—C18	124.4 (3)
C9—C8—H8	118.9	N4—C19—H19	117.8
C8—C9—C10	119.1 (2)	C18—C19—H19	117.8
C8—C9—H9	120.5	C12—N1—C8	119.1 (2)
C10—C9—H9	120.5	C12—N1—H1A	120.5
C9—C10—C11	118.7 (2)	C8—N1—H1A	120.5
C9—C10—C13	119.94 (19)	C13—N2—N3	106.18 (17)
C11—C10—C13	121.35 (18)	C14—N3—N2	106.04 (17)
C12—C11—C10	118.5 (2)	C15—N4—C19	115.6 (2)
C12—C11—H11	120.7	C13—O3—C14	102.71 (15)
O1—C1—C2—C7	−7.7 (3)	C15—C16—C17—C18	0.1 (4)
O2—C1—C2—C7	171.85 (19)	C15—C16—C17—C14	−178.0 (2)
O1—C1—C2—C3	172.7 (2)	N3—C14—C17—C18	−167.8 (2)
O2—C1—C2—C3	−7.7 (3)	O3—C14—C17—C18	9.0 (3)
C7—C2—C3—C4	0.0 (3)	N3—C14—C17—C16	10.2 (4)
C1—C2—C3—C4	179.54 (19)	O3—C14—C17—C16	−172.9 (2)
C2—C3—C4—C5	−0.5 (3)	C16—C17—C18—C19	−0.3 (4)
C3—C4—C5—C6	0.4 (4)	C14—C17—C18—C19	177.8 (2)
C4—C5—C6—C7	0.3 (4)	C17—C18—C19—N4	0.6 (4)
C5—C6—C7—C2	−0.8 (4)	C11—C12—N1—C8	−0.6 (3)
C3—C2—C7—C6	0.7 (3)	C9—C8—N1—C12	−0.9 (4)
C1—C2—C7—C6	−178.9 (2)	O3—C13—N2—N3	−0.5 (2)
N1—C8—C9—C10	1.5 (4)	C10—C13—N2—N3	179.14 (19)
C8—C9—C10—C11	−0.6 (3)	O3—C14—N3—N2	−0.4 (2)
C8—C9—C10—C13	179.7 (2)	C17—C14—N3—N2	176.6 (2)
C9—C10—C11—C12	−0.8 (3)	C13—N2—N3—C14	0.5 (2)
C13—C10—C11—C12	178.89 (19)	C16—C15—N4—C19	0.3 (4)
C10—C11—C12—N1	1.4 (3)	C18—C19—N4—C15	−0.5 (4)
C9—C10—C13—N2	2.8 (3)	N2—C13—O3—C14	0.2 (2)
C11—C10—C13—N2	−176.8 (2)	C10—C13—O3—C14	−179.42 (17)
C9—C10—C13—O3	−177.63 (18)	N3—C14—O3—C13	0.1 (2)
C11—C10—C13—O3	2.7 (3)	C17—C14—O3—C13	−177.24 (18)
N4—C15—C16—C17	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	1.79	2.648 (2)	174
C8—H8···O1ii	0.93	2.48	3.371 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	1.79	2.648 (2)	174
C8—H8⋯O1ii	0.93	2.48	3.371 (3)	161

Symmetry codes: (i) ; (ii) .