Benzene-1,2-dicarb-oxy-lic acid-pyridinium-2-olate (1/1).

The asymmetric unit of the title compound, C(5)H(5)NO·C(8)H(6)O(4), contains one o-phthalate acid mol-ecule and one pyridin-2-ol mol-ecule, which exists in a zwitterionic form. In the o-phthalate acid mol-ecule, the carboxyl-ate groups are twisted from the benzene ring by dihedral angles of 13.6 (1)° and 73.1 (1)°; the hy-droxy H atom in the latter group is disordered over two positons in a 1:1 ratio. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains in [-101].

Related literature

For background to molecular ferroelectrics, see: Zhang et al. (2009 ▶, 2010 ▶, 2012 ▶). For a related structure, see: Zhu & Yu (2011 ▶).

Experimental

Crystal data

C5H5NO·C8H6O4

M = 261.23

Triclinic,

a = 7.4529 (15) Å

b = 7.7925 (16) Å

c = 11.489 (2) Å

α = 84.42 (3)°

β = 84.29 (3)°

γ = 70.30 (3)°

V = 623.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.34 × 0.30 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.964, T max = 0.970

6555 measured reflections

2864 independent reflections

1687 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.174

S = 1.06

2864 reflections

184 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.21 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: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023914/cv5304sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023914/cv5304Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023914/cv5304Isup3.cml

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

C5H5NO·C8H6O4	Z = 2
Mr = 261.23	F(000) = 272
Triclinic, P1	Dx = 1.391 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4529 (15) Å	Cell parameters from 2864 reflections
b = 7.7925 (16) Å	θ = 3.2–27.5°
c = 11.489 (2) Å	µ = 0.11 mm−1
α = 84.42 (3)°	T = 293 K
β = 84.29 (3)°	Block, colourless
γ = 70.30 (3)°	0.34 × 0.30 × 0.28 mm
V = 623.6 (2) Å3

Rigaku, SCXmini diffractometer	1687 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	k = −10→10
Tmin = 0.964, Tmax = 0.970	l = −14→14
6555 measured reflections	3 standard reflections every 180 reflections
2864 independent reflections	intensity decay: none

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0891P)2] where P = (Fo2 + 2Fc2)/3
2864 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.20 e Å−3
6 restraints	Δρmin = −0.21 e Å−3

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	Occ. (<1)
C1	0.3559 (3)	0.3156 (3)	0.68465 (17)	0.0443 (5)
C2	0.5446 (3)	0.2808 (3)	0.6408 (2)	0.0567 (6)
H2	0.5713	0.3150	0.5629	0.068*
C3	0.6907 (3)	0.1969 (3)	0.7113 (2)	0.0662 (7)
H3	0.8165	0.1738	0.6811	0.079*
C4	0.6532 (3)	0.1465 (3)	0.8262 (2)	0.0633 (6)
H4	0.7537	0.0872	0.8732	0.076*
C5	0.4692 (3)	0.1827 (3)	0.87225 (18)	0.0532 (6)
H5	0.4452	0.1500	0.9508	0.064*
C6	0.3168 (3)	0.2685 (3)	0.80241 (17)	0.0433 (5)
C7	0.1172 (3)	0.3228 (3)	0.85256 (18)	0.0508 (5)
C8	0.2024 (3)	0.3968 (3)	0.60303 (16)	0.0456 (5)
C9	0.3260 (3)	0.6814 (3)	0.87731 (18)	0.0491 (5)
C10	0.2091 (3)	0.8029 (3)	0.7956 (2)	0.0623 (6)
H10	0.0770	0.8389	0.8093	0.075*
C11	0.2866 (4)	0.8680 (3)	0.6973 (2)	0.0665 (7)
H11	0.2069	0.9480	0.6440	0.080*
C12	0.4816 (4)	0.8177 (3)	0.6746 (2)	0.0632 (6)
H12	0.5342	0.8633	0.6068	0.076*
C13	0.5943 (3)	0.7015 (3)	0.7522 (2)	0.0611 (6)
H13	0.7264	0.6659	0.7385	0.073*
H3A	0.063 (5)	0.612 (8)	0.532 (5)	0.11 (2)*	0.50
H3A'	0.038 (5)	0.352 (5)	0.521 (3)	0.11 (2)*	0.50
H1B	−0.026 (3)	0.294 (4)	0.983 (2)	0.092 (10)*
N1	0.5161 (3)	0.6359 (2)	0.85064 (15)	0.0547 (5)
H1A	0.5917	0.5613	0.8987	0.066*
O1	0.0910 (3)	0.2509 (2)	0.95711 (14)	0.0729 (5)
O2	−0.0108 (2)	0.4285 (3)	0.79990 (16)	0.0876 (6)
O3	0.1680 (3)	0.5598 (2)	0.56473 (16)	0.0723 (5)
O4	0.1233 (3)	0.2930 (2)	0.56793 (15)	0.0696 (5)
O5	0.2656 (2)	0.6139 (2)	0.97148 (13)	0.0663 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0418 (11)	0.0481 (11)	0.0449 (11)	−0.0178 (9)	−0.0053 (9)	0.0001 (9)
C2	0.0510 (13)	0.0692 (15)	0.0519 (12)	−0.0261 (11)	0.0056 (11)	−0.0011 (11)
C3	0.0394 (12)	0.0793 (17)	0.0794 (17)	−0.0192 (12)	−0.0011 (12)	−0.0083 (13)
C4	0.0457 (14)	0.0684 (15)	0.0716 (16)	−0.0089 (11)	−0.0185 (12)	−0.0064 (12)
C5	0.0539 (13)	0.0566 (13)	0.0462 (12)	−0.0129 (10)	−0.0119 (10)	−0.0016 (10)
C6	0.0418 (11)	0.0464 (11)	0.0414 (11)	−0.0142 (9)	−0.0052 (9)	0.0000 (8)
C7	0.0486 (13)	0.0613 (13)	0.0412 (11)	−0.0177 (11)	−0.0029 (10)	0.0010 (10)
C8	0.0490 (12)	0.0524 (13)	0.0377 (10)	−0.0221 (10)	−0.0026 (9)	0.0045 (9)
C9	0.0498 (12)	0.0537 (12)	0.0409 (11)	−0.0147 (10)	0.0057 (9)	−0.0065 (9)
C10	0.0552 (14)	0.0587 (14)	0.0626 (14)	−0.0072 (11)	−0.0008 (11)	−0.0015 (11)
C11	0.0803 (18)	0.0523 (14)	0.0582 (15)	−0.0121 (12)	−0.0107 (13)	0.0073 (11)
C12	0.0769 (17)	0.0550 (13)	0.0524 (13)	−0.0210 (12)	0.0078 (12)	0.0058 (11)
C13	0.0585 (14)	0.0608 (14)	0.0580 (14)	−0.0169 (11)	0.0108 (11)	0.0000 (11)
N1	0.0523 (11)	0.0583 (11)	0.0472 (10)	−0.0121 (9)	−0.0012 (9)	0.0028 (8)
O1	0.0565 (11)	0.0911 (13)	0.0538 (10)	−0.0116 (9)	0.0091 (8)	0.0177 (9)
O2	0.0456 (10)	0.1286 (16)	0.0627 (11)	−0.0037 (10)	−0.0012 (8)	0.0241 (10)
O3	0.0820 (13)	0.0609 (11)	0.0843 (12)	−0.0359 (9)	−0.0379 (10)	0.0231 (9)
O4	0.0824 (12)	0.0601 (10)	0.0769 (12)	−0.0331 (9)	−0.0393 (10)	0.0142 (9)
O5	0.0584 (10)	0.0838 (11)	0.0494 (9)	−0.0192 (8)	0.0075 (8)	0.0033 (8)

C1—C2	1.391 (3)	C9—O5	1.266 (2)
C1—C6	1.396 (3)	C9—N1	1.351 (3)
C1—C8	1.483 (3)	C9—C10	1.404 (3)
C2—C3	1.365 (3)	C10—C11	1.350 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.370 (4)	C11—C12	1.377 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.365 (3)	C12—C13	1.342 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.395 (3)	C13—N1	1.355 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.475 (3)	N1—H1A	0.8600
C7—O2	1.201 (3)	O1—H1B	0.85 (2)
C7—O1	1.300 (2)	O3—H3A	0.855 (15)
C8—O3	1.252 (2)	O4—H3A'	0.85 (3)
C8—O4	1.263 (2)
C2—C1—C6	119.45 (19)	O4—C8—C1	117.90 (18)
C2—C1—C8	118.47 (18)	O5—C9—N1	119.3 (2)
C6—C1—C8	122.05 (17)	O5—C9—C10	124.9 (2)
C3—C2—C1	120.4 (2)	N1—C9—C10	115.89 (19)
C3—C2—H2	119.8	C11—C10—C9	120.7 (2)
C1—C2—H2	119.8	C11—C10—H10	119.7
C2—C3—C4	120.4 (2)	C9—C10—H10	119.7
C2—C3—H3	119.8	C10—C11—C12	121.1 (2)
C4—C3—H3	119.8	C10—C11—H11	119.5
C5—C4—C3	120.4 (2)	C12—C11—H11	119.5
C5—C4—H4	119.8	C13—C12—C11	118.6 (2)
C3—C4—H4	119.8	C13—C12—H12	120.7
C4—C5—C6	120.5 (2)	C11—C12—H12	120.7
C4—C5—H5	119.7	C12—C13—N1	120.2 (2)
C6—C5—H5	119.7	C12—C13—H13	119.9
C5—C6—C1	118.79 (19)	N1—C13—H13	119.9
C5—C6—C7	121.36 (18)	C9—N1—C13	123.6 (2)
C1—C6—C7	119.67 (18)	C9—N1—H1A	118.2
O2—C7—O1	122.9 (2)	C13—N1—H1A	118.2
O2—C7—C6	121.49 (18)	C7—O1—H1B	110 (2)
O1—C7—C6	115.58 (19)	C8—O3—H3A	117 (4)
O3—C8—O4	122.96 (19)	C8—O4—H3A'	111 (3)
O3—C8—C1	118.87 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4i	0.86 (2)	1.80 (2)	2.644 (3)	167 (7)
O4—H3A′···O3i	0.85 (3)	1.81 (3)	2.644 (3)	167 (4)
O1—H1B···O5ii	0.85 (2)	1.74 (2)	2.587 (2)	178 (3)
N1—H1A···O5iii	0.86	2.04	2.892 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4i	0.86 (2)	1.80 (2)	2.644 (3)	167 (7)
O4—H3A′⋯O3i	0.85 (3)	1.81 (3)	2.644 (3)	167 (4)
O1—H1B⋯O5ii	0.85 (2)	1.74 (2)	2.587 (2)	178 (3)
N1—H1A⋯O5iii	0.86	2.04	2.892 (3)	171

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