Pyridinium-2-carboxyl-ate-benzene-1,2-diol (1/1).

The title compound, C(6)H(5)NO(2)·C(6)H(6)O(2), crystallizes with one pyridinium-2-carboxyl-ate zwitterion and one mol-ecule of benzene-1,2-diol in the asymmetric unit. The crystal structure is characterized by alternating mol-ecules forming zigzag chains running along the a axis: the mol-ecules are connected by O-H⋯O and N-H⋯(O,O) hydrogen bonds.

Related literature

For co-crystallization experiments, see: Ton & Bolte (2005 ▶); Tutughamiarso et al. (2009 ▶).

Experimental

Crystal data

C6H5NO2·C6H6O2

M = 233.22

Orthorhombic,

a = 6.9710 (14) Å

b = 6.9855 (14) Å

c = 21.806 (4) Å

V = 1061.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.21 × 0.18 × 0.16 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

11928 measured reflections

1196 independent reflections

1105 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.096

wR(F 2) = 0.197

S = 1.23

1196 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.34 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: PLATON (Spek, 2009 ▶) and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043207/ng2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043207/ng2670Isup2.hkl

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

C6H5NO2·C6H6O2	F(000) = 488
Mr = 233.22	Dx = 1.459 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6345 reflections
a = 6.9710 (14) Å	θ = 3.5–24.3°
b = 6.9855 (14) Å	µ = 0.11 mm−1
c = 21.806 (4) Å	T = 173 K
V = 1061.9 (4) Å3	Block, colourless
Z = 4	0.21 × 0.18 × 0.16 mm

Stoe IPDSII two-circle diffractometer	1105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
graphite	θmax = 25.8°, θmin = 3.1°
ω scans	h = −8→8
11928 measured reflections	k = −8→8
1196 independent reflections	l = −26→25

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)] = 0.096	H-atom parameters constrained
wR(F2) = 0.197	w = 1/[σ2(Fo2) + (0.0513P)2 + 3.5668P] where P = (Fo2 + 2Fc2)/3
S = 1.23	(Δ/σ)max = 0.001
1196 reflections	Δρmax = 0.44 e Å−3
155 parameters	Δρmin = −0.34 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: 0.036 (6)

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	1.1064 (7)	0.3802 (7)	0.0845 (2)	0.0257 (11)
H1	1.2093	0.4153	0.0679	0.039*
O2	0.8174 (6)	0.1866 (8)	0.1466 (2)	0.0295 (12)
H2	0.7994	0.2756	0.1214	0.044*
C1	1.1455 (9)	0.3029 (9)	0.1410 (3)	0.0200 (13)
C2	0.9985 (9)	0.2048 (10)	0.1716 (3)	0.0220 (13)
C3	1.0330 (10)	0.1145 (11)	0.2274 (3)	0.0259 (14)
H3	0.9332	0.0460	0.2473	0.031*
C4	1.2160 (10)	0.1249 (11)	0.2542 (3)	0.0303 (16)
H4	1.2399	0.0649	0.2925	0.036*
C5	1.3612 (9)	0.2231 (10)	0.2244 (3)	0.0280 (15)
H5	1.4850	0.2302	0.2424	0.034*
C6	1.3273 (9)	0.3110 (10)	0.1686 (3)	0.0254 (14)
H6	1.4284	0.3777	0.1487	0.031*
O11	0.3875 (7)	0.5038 (7)	0.0125 (2)	0.0307 (12)
O12	0.6497 (8)	0.4131 (10)	0.0643 (3)	0.0516 (18)
N1	0.8827 (8)	0.5092 (8)	−0.0246 (2)	0.0222 (12)
H31	0.9086	0.4912	0.0160	0.027*
C11	1.0169 (10)	0.5516 (10)	−0.0666 (3)	0.0260 (15)
H11	1.1479	0.5226	−0.0591	0.031*
C13	0.6922 (9)	0.5494 (9)	−0.0326 (3)	0.0208 (13)
C14	0.6360 (10)	0.6404 (9)	−0.0853 (3)	0.0237 (14)
H14	0.5049	0.6725	−0.0914	0.028*
C15	0.7722 (10)	0.6856 (10)	−0.1299 (3)	0.0275 (15)
H15	0.7347	0.7491	−0.1665	0.033*
C16	0.9629 (10)	0.6368 (11)	−0.1202 (3)	0.0301 (17)
H16	1.0559	0.6628	−0.1510	0.036*
C131	0.5649 (10)	0.4815 (11)	0.0200 (3)	0.0283 (15)

	U11	U22	U33	U12	U13	U23
O1	0.015 (2)	0.032 (2)	0.030 (2)	−0.002 (2)	0.0002 (18)	0.006 (2)
O2	0.015 (2)	0.033 (3)	0.041 (3)	−0.005 (2)	−0.003 (2)	0.007 (2)
C1	0.017 (3)	0.015 (3)	0.028 (3)	−0.007 (3)	0.002 (3)	−0.001 (3)
C2	0.017 (3)	0.020 (3)	0.029 (3)	−0.004 (3)	0.000 (3)	−0.003 (3)
C3	0.025 (3)	0.026 (3)	0.027 (3)	−0.002 (3)	0.006 (3)	−0.002 (3)
C4	0.032 (4)	0.034 (4)	0.026 (3)	0.001 (3)	−0.004 (3)	0.006 (3)
C5	0.019 (3)	0.035 (4)	0.030 (3)	0.000 (3)	−0.004 (3)	−0.003 (3)
C6	0.019 (3)	0.029 (3)	0.028 (3)	−0.005 (3)	0.003 (3)	−0.003 (3)
O11	0.016 (2)	0.043 (3)	0.033 (2)	−0.002 (2)	0.002 (2)	0.002 (3)
O12	0.024 (3)	0.086 (5)	0.044 (3)	0.015 (3)	0.007 (2)	0.033 (3)
N1	0.019 (3)	0.025 (3)	0.023 (2)	0.004 (3)	0.001 (2)	0.000 (2)
C11	0.022 (3)	0.022 (3)	0.034 (3)	0.000 (3)	0.005 (3)	−0.002 (3)
C13	0.015 (3)	0.015 (3)	0.033 (3)	−0.001 (2)	0.002 (3)	0.000 (3)
C14	0.019 (3)	0.025 (3)	0.027 (3)	0.000 (3)	−0.002 (3)	0.002 (3)
C15	0.038 (4)	0.021 (3)	0.024 (3)	−0.001 (3)	−0.002 (3)	−0.002 (3)
C16	0.028 (4)	0.034 (4)	0.028 (3)	−0.001 (3)	0.004 (3)	0.002 (3)
C131	0.028 (4)	0.028 (3)	0.029 (3)	0.004 (3)	0.003 (3)	0.005 (3)

O1—C1	1.374 (8)	O11—C131	1.257 (8)
O1—H1	0.8397	O12—C131	1.229 (9)
O2—C2	1.381 (7)	N1—C11	1.342 (9)
O2—H2	0.8392	N1—C13	1.368 (8)
C1—C2	1.401 (9)	N1—H31	0.9123
C1—C6	1.404 (9)	C11—C16	1.365 (10)
C2—C3	1.391 (9)	C11—H11	0.9500
C3—C4	1.405 (9)	C13—C14	1.370 (9)
C3—H3	0.9500	C13—C131	1.526 (9)
C4—C5	1.384 (10)	C14—C15	1.396 (10)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.383 (9)	C15—C16	1.389 (10)
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500	C16—H16	0.9500
C1—O1—H1	109.4	C11—N1—H31	123.7
C2—O2—H2	109.1	C13—N1—H31	110.1
O1—C1—C2	118.3 (5)	N1—C11—C16	119.3 (7)
O1—C1—C6	123.2 (5)	N1—C11—H11	120.4
C2—C1—C6	118.5 (6)	C16—C11—H11	120.4
O2—C2—C3	117.5 (6)	N1—C13—C14	118.6 (6)
O2—C2—C1	121.7 (6)	N1—C13—C131	113.9 (6)
C3—C2—C1	120.7 (6)	C14—C13—C131	127.4 (6)
C2—C3—C4	119.8 (6)	C13—C14—C15	119.7 (6)
C2—C3—H3	120.1	C13—C14—H14	120.2
C4—C3—H3	120.1	C15—C14—H14	120.2
C5—C4—C3	119.6 (6)	C16—C15—C14	119.4 (6)
C5—C4—H4	120.2	C16—C15—H15	120.3
C3—C4—H4	120.2	C14—C15—H15	120.3
C6—C5—C4	120.5 (6)	C11—C16—C15	120.0 (7)
C6—C5—H5	119.8	C11—C16—H16	120.0
C4—C5—H5	119.8	C15—C16—H16	120.0
C5—C6—C1	120.9 (6)	O12—C131—O11	128.6 (7)
C5—C6—H6	119.6	O12—C131—C13	115.6 (6)
C1—C6—H6	119.6	O11—C131—C13	115.8 (6)
C11—N1—C13	123.0 (6)
O1—C1—C2—O2	−0.7 (10)	C11—N1—C13—C14	−1.3 (10)
C6—C1—C2—O2	−178.3 (6)	C11—N1—C13—C131	177.8 (6)
O1—C1—C2—C3	176.4 (6)	N1—C13—C14—C15	1.5 (9)
C6—C1—C2—C3	−1.2 (10)	C131—C13—C14—C15	−177.4 (6)
O2—C2—C3—C4	178.6 (6)	C13—C14—C15—C16	0.2 (10)
C1—C2—C3—C4	1.4 (10)	N1—C11—C16—C15	2.5 (11)
C2—C3—C4—C5	−0.8 (11)	C14—C15—C16—C11	−2.3 (11)
C3—C4—C5—C6	0.1 (11)	N1—C13—C131—O12	5.1 (9)
C4—C5—C6—C1	0.1 (11)	C14—C13—C131—O12	−176.0 (7)
O1—C1—C6—C5	−177.0 (6)	N1—C13—C131—O11	−175.2 (6)
C2—C1—C6—C5	0.5 (10)	C14—C13—C131—O11	3.7 (10)
C13—N1—C11—C16	−0.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O11i	0.84	1.84	2.655 (6)	163
O2—H2···O12	0.84	1.89	2.662 (7)	153
N1—H31···O12	0.91	2.16	2.617 (7)	110
N1—H31···O1	0.91	2.18	2.984 (7)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O11i	0.84	1.84	2.655 (6)	163
O2—H2⋯O12	0.84	1.89	2.662 (7)	153
N1—H31⋯O12	0.91	2.16	2.617 (7)	110
N1—H31⋯O1	0.91	2.18	2.984 (7)	147

Symmetry code: (i) .