2-Amino-5-(4-carboxyl-atophen-yl)-pyridinium monohydrate.

The title compound, C(12)H(10)N(2)O(2)·H(2)O, crystallizes as a zwitterion in which the pyridine N atom is protonated and the carb-oxy -OH group is deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 6.63 (5)° between them. In the crystal, inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions link adjacent mol-ecules into a two-dimensional double layered supra-molecular network.

Related literature

For the use of pyridine­n class="Chemical">carboxyl­ate acid in coordination chemistry and for related structures, see: Jia et al. (2007 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

C12H10N2O2·n class="Chemical">H2O

M = 232.24

Monoclinic,

a = 7.796 (2) Å

b = 7.808 (2) Å

c = 18.480 (5) Å

β = 95.165 (14)°

V = 1120.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.23 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.985

11449 measured reflections

2554 independent reflections

1505 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.208

S = 1.01

2554 reflections

160 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812035854/jj2150sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035854/jj2150Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035854/jj2150Isup3.cml

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

C12H10N2O2·H2O	F(000) = 488
Mr = 232.24	Dx = 1.377 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yn	Cell parameters from 1672 reflections
a = 7.796 (2) Å	θ = 2.8–27.5°
b = 7.808 (2) Å	µ = 0.10 mm−1
c = 18.480 (5) Å	T = 296 K
β = 95.165 (14)°	Prism, colorless
V = 1120.4 (6) Å3	0.23 × 0.16 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	2554 independent reflections
Radiation source: fine-focus sealed tube	1505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
phi and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.977, Tmax = 0.985	k = −10→10
11449 measured reflections	l = −23→24

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0766P)2 + 0.595P] where P = (Fo2 + 2Fc2)/3
2554 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.17 e Å−3
3 restraints	Δρmin = −0.16 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
C1	0.5962 (4)	0.7159 (4)	0.15326 (17)	0.0568 (8)
C2	0.6222 (4)	0.7885 (4)	0.08526 (18)	0.0669 (9)
H2C	0.6003	0.9042	0.0767	0.080*
C3	0.6796 (4)	0.6884 (4)	0.03225 (17)	0.0647 (9)
H3A	0.6927	0.7373	−0.0128	0.078*
C4	0.7203 (4)	0.5123 (4)	0.04277 (15)	0.0522 (7)
C5	0.6949 (4)	0.4505 (4)	0.11010 (16)	0.0600 (8)
H5A	0.7200	0.3362	0.1205	0.072*
C6	0.7823 (4)	0.4004 (4)	−0.01377 (15)	0.0528 (7)
C7	0.8241 (4)	0.4649 (4)	−0.08022 (16)	0.0642 (9)
H7B	0.8121	0.5815	−0.0895	0.077*
C8	0.8830 (4)	0.3594 (4)	−0.13264 (16)	0.0648 (9)
H8C	0.9119	0.4067	−0.1761	0.078*
C9	0.8999 (4)	0.1853 (4)	−0.12169 (15)	0.0555 (7)
C10	0.8584 (5)	0.1196 (4)	−0.05641 (17)	0.0728 (10)
H10A	0.8683	0.0025	−0.0478	0.087*
C11	0.8022 (5)	0.2251 (4)	−0.00347 (18)	0.0770 (11)
H11A	0.7770	0.1774	0.0404	0.092*
C12	0.9664 (4)	0.0670 (4)	−0.17777 (17)	0.0634 (8)
N1	0.6345 (3)	0.5496 (3)	0.16235 (13)	0.0606 (7)
H1A	0.6200	0.5033	0.2036	0.073*
N2	0.5351 (3)	0.8023 (4)	0.20782 (15)	0.0693 (8)
H2A	0.5210	0.7511	0.2481	0.083*
H2B	0.5100	0.9091	0.2027	0.083*
O1	1.0359 (3)	0.1364 (3)	−0.22902 (12)	0.0757 (7)
O2	0.9515 (4)	−0.0921 (3)	−0.17007 (13)	0.0853 (8)
O3	0.4085 (4)	1.1412 (3)	0.16247 (15)	0.0866 (8)
H3C	0.300 (3)	1.128 (6)	0.165 (2)	0.130*
H3D	0.447 (5)	1.207 (5)	0.1977 (19)	0.130*

	U11	U22	U33	U12	U13	U23
C1	0.0564 (17)	0.0549 (18)	0.0606 (19)	−0.0067 (14)	0.0137 (14)	−0.0057 (14)
C2	0.085 (2)	0.0504 (17)	0.068 (2)	−0.0074 (16)	0.0206 (17)	0.0030 (16)
C3	0.082 (2)	0.0570 (18)	0.0581 (19)	−0.0106 (16)	0.0216 (16)	0.0042 (15)
C4	0.0583 (17)	0.0535 (17)	0.0454 (16)	−0.0112 (14)	0.0088 (13)	0.0015 (12)
C5	0.075 (2)	0.0542 (17)	0.0516 (17)	0.0010 (16)	0.0116 (15)	0.0009 (14)
C6	0.0579 (17)	0.0570 (17)	0.0441 (16)	−0.0110 (14)	0.0079 (13)	−0.0008 (13)
C7	0.091 (2)	0.0542 (17)	0.0480 (17)	−0.0022 (17)	0.0119 (16)	0.0042 (14)
C8	0.091 (2)	0.065 (2)	0.0397 (16)	−0.0048 (18)	0.0144 (15)	0.0046 (14)
C9	0.0617 (17)	0.0595 (18)	0.0452 (16)	−0.0059 (14)	0.0042 (13)	−0.0028 (13)
C10	0.109 (3)	0.058 (2)	0.0543 (19)	0.0010 (19)	0.0242 (18)	0.0045 (15)
C11	0.124 (3)	0.058 (2)	0.0527 (18)	−0.003 (2)	0.0330 (19)	0.0092 (15)
C12	0.072 (2)	0.069 (2)	0.0497 (18)	−0.0034 (17)	0.0087 (15)	−0.0035 (16)
N1	0.0786 (17)	0.0604 (16)	0.0444 (14)	−0.0014 (13)	0.0153 (12)	0.0001 (12)
N2	0.0809 (18)	0.0634 (16)	0.0668 (17)	−0.0017 (14)	0.0254 (15)	−0.0080 (13)
O1	0.1006 (18)	0.0747 (15)	0.0557 (13)	−0.0044 (13)	0.0287 (13)	−0.0042 (11)
O2	0.130 (2)	0.0615 (15)	0.0686 (16)	−0.0009 (15)	0.0326 (15)	−0.0012 (12)
O3	0.117 (2)	0.0677 (16)	0.0786 (18)	−0.0107 (16)	0.0272 (16)	−0.0095 (13)

C1—N2	1.336 (4)	C8—C9	1.379 (4)
C1—N1	1.339 (4)	C8—H8C	0.9300
C1—C2	1.410 (4)	C9—C10	1.376 (4)
C2—C3	1.360 (4)	C9—C12	1.514 (4)
C2—H2C	0.9300	C10—C11	1.380 (4)
C3—C4	1.421 (4)	C10—H10A	0.9300
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.365 (4)	C12—O1	1.256 (4)
C4—C6	1.477 (4)	C12—O2	1.257 (4)
C5—N1	1.355 (4)	N1—H1A	0.8600
C5—H5A	0.9300	N2—H2A	0.8600
C6—C11	1.389 (4)	N2—H2B	0.8600
C6—C7	1.393 (4)	O3—H3C	0.860 (18)
C7—C8	1.381 (4)	O3—H3D	0.861 (18)
C7—H7B	0.9300
N2—C1—N1	119.0 (3)	C9—C8—H8C	119.4
N2—C1—C2	124.0 (3)	C7—C8—H8C	119.4
N1—C1—C2	117.0 (3)	C10—C9—C8	118.0 (3)
C3—C2—C1	119.6 (3)	C10—C9—C12	119.6 (3)
C3—C2—H2C	120.2	C8—C9—C12	122.3 (3)
C1—C2—H2C	120.2	C9—C10—C11	120.9 (3)
C2—C3—C4	122.8 (3)	C9—C10—H10A	119.6
C2—C3—H3A	118.6	C11—C10—H10A	119.6
C4—C3—H3A	118.6	C10—C11—C6	122.0 (3)
C5—C4—C3	114.7 (3)	C10—C11—H11A	119.0
C5—C4—C6	121.3 (3)	C6—C11—H11A	119.0
C3—C4—C6	124.0 (3)	O1—C12—O2	124.3 (3)
N1—C5—C4	122.4 (3)	O1—C12—C9	116.8 (3)
N1—C5—H5A	118.8	O2—C12—C9	119.0 (3)
C4—C5—H5A	118.8	C1—N1—C5	123.5 (3)
C11—C6—C7	116.4 (3)	C1—N1—H1A	118.2
C11—C6—C4	121.7 (3)	C5—N1—H1A	118.2
C7—C6—C4	121.8 (3)	C1—N2—H2A	120.0
C8—C7—C6	121.4 (3)	C1—N2—H2B	120.0
C8—C7—H7B	119.3	H2A—N2—H2B	120.0
C6—C7—H7B	119.3	H3C—O3—H3D	108 (3)
C9—C8—C7	121.2 (3)
N2—C1—C2—C3	−177.8 (3)	C7—C8—C9—C10	−0.8 (5)
N1—C1—C2—C3	1.7 (5)	C7—C8—C9—C12	−179.2 (3)
C1—C2—C3—C4	−2.0 (5)	C8—C9—C10—C11	−0.3 (5)
C2—C3—C4—C5	0.9 (5)	C12—C9—C10—C11	178.1 (3)
C2—C3—C4—C6	179.8 (3)	C9—C10—C11—C6	1.1 (6)
C3—C4—C5—N1	0.4 (4)	C7—C6—C11—C10	−0.8 (5)
C6—C4—C5—N1	−178.5 (3)	C4—C6—C11—C10	179.3 (3)
C5—C4—C6—C11	6.1 (5)	C10—C9—C12—O1	−165.4 (3)
C3—C4—C6—C11	−172.8 (3)	C8—C9—C12—O1	12.9 (5)
C5—C4—C6—C7	−173.9 (3)	C10—C9—C12—O2	13.6 (5)
C3—C4—C6—C7	7.3 (5)	C8—C9—C12—O2	−168.1 (3)
C11—C6—C7—C8	−0.3 (5)	N2—C1—N1—C5	179.1 (3)
C4—C6—C7—C8	179.6 (3)	C2—C1—N1—C5	−0.4 (5)
C6—C7—C8—C9	1.2 (5)	C4—C5—N1—C1	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	1.82	2.648 (3)	160
N2—H2A···O2i	0.86	2.07	2.911 (4)	167
N2—H2B···O3	0.86	2.09	2.921 (4)	163
O3—H3C···O2ii	0.86 (2)	1.99 (2)	2.849 (4)	178 (4)
O3—H3D···O1iii	0.86 (2)	1.91 (2)	2.768 (4)	176 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	1.82	2.648 (3)	160
N2—H2A⋯O2i	0.86	2.07	2.911 (4)	167
N2—H2B⋯O3	0.86	2.09	2.921 (4)	163
O3—H3C⋯O2ii	0.86 (2)	1.99 (2)	2.849 (4)	178 (4)
O3—H3D⋯O1iii	0.86 (2)	1.91 (2)	2.768 (4)	176 (5)

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