3-Carb-oxy-quinolin-1-ium-2-carboxyl-ate monohydrate.

The title compound, C(11)H(7)NO(4)·H(2)O, contains a 3-carb-oxy-quinolin-1-ium-2-carboxyl-ate (qda) zwitterion and one water mol-ecule. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers, and these dimers are further connected by O-H⋯O hydrogen bonds into a three-dimensional supra-molecular architecture. In addition, π-π inter-actions occur between pyridine and benzene rings from different qda ligands [centroid-centroid distance = 3.749 (1) Å] and the dihedral angles of the -CO(2)H and -CO(2) groups to the quinoline system are 8.47 (3) and 88.16 (6)°, respectively.

Related literature

For background on the use of quinoline carb­oxy­lic acid derivatives in metal organic frameworks, see: Dobrzyńska et al. (2004 ▶, 2005 ▶); Hu et al. (2007 ▶); Li & Liu (2010 ▶). For background on the role of noncovalent inter­molecular inter­actions, see: Wang et al. (2011 ▶). For related structures, see: Dobrzyńska et al. (2004 ▶); Dobrzyńska & Jerzykiewicz (2008 ▶); Odoko et al. (2001 ▶); Zurowska et al. (2007 ▶).

Experimental

Crystal data

C11H7NO4·H2O

M = 235.19

Monoclinic,

a = 7.5424 (15) Å

b = 14.422 (3) Å

c = 9.755 (2) Å

β = 108.17 (3)°

V = 1008.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 153 K

0.15 × 0.13 × 0.11 mm

Data collection

Rigaku CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.981, T max = 1

4586 measured reflections

1817 independent reflections

1547 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.05

1817 reflections

168 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); 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: CrystalClear (Rigaku, 2007 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006988/zj2053sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006988/zj2053Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006988/zj2053Isup3.cml

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

C11H7NO4·H2O	F(000) = 488
Mr = 235.19	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4018 reflections
a = 7.5424 (15) Å	θ = 4.0–28.9°
b = 14.422 (3) Å	µ = 0.13 mm−1
c = 9.755 (2) Å	T = 153 K
β = 108.17 (3)°	Prism, colourless
V = 1008.3 (4) Å3	0.15 × 0.13 × 0.11 mm
Z = 4

Rigaku CCD area-detector diffractometer	1817 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 28.5714 pixels mm-1	θmax = 25.3°, θmin = 4.0°
ω scans	h = −8→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −17→15
Tmin = 0.981, Tmax = 1	l = −8→11
4586 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.0617P] where P = (Fo2 + 2Fc2)/3
1817 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.20 e Å−3
5 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.65319 (19)	0.09213 (9)	1.05483 (14)	0.0216 (3)
C2	0.67451 (18)	0.30200 (9)	1.06906 (15)	0.0216 (3)
C3	0.54746 (17)	0.25508 (9)	0.93895 (14)	0.0195 (3)
C4	0.54008 (17)	0.15740 (9)	0.93584 (14)	0.0194 (3)
C5	0.31108 (17)	0.16028 (10)	0.70347 (14)	0.0199 (3)
C6	0.31153 (18)	0.25796 (9)	0.70374 (14)	0.0192 (3)
C7	0.19098 (18)	0.30475 (10)	0.58263 (14)	0.0231 (3)
H7	0.1883	0.3692	0.5804	0.028*
C8	0.07928 (19)	0.25556 (10)	0.46975 (16)	0.0255 (3)
H8	0.0000	0.2867	0.3909	0.031*
C9	0.08227 (19)	0.15775 (10)	0.47086 (15)	0.0266 (3)
H9	0.0054	0.1253	0.3923	0.032*
C10	0.19651 (19)	0.10985 (10)	0.58570 (15)	0.0254 (3)
H10	0.1983	0.0454	0.5858	0.031*
C11	0.43333 (17)	0.30389 (9)	0.82448 (14)	0.0197 (3)
H11	0.4362	0.3684	0.8265	0.024*
O1	0.80640 (13)	0.06645 (7)	1.04539 (11)	0.0322 (3)
O2	0.57317 (13)	0.06656 (6)	1.14257 (10)	0.0241 (3)
O3	0.75594 (15)	0.25971 (7)	1.17666 (11)	0.0346 (3)
N1	0.42599 (15)	0.11485 (8)	0.82176 (11)	0.0206 (3)
H1A	0.418 (2)	0.0503 (15)	0.8245 (19)	0.046 (5)*
O1W	0.88294 (16)	0.02969 (8)	0.79197 (12)	0.0380 (3)
H1C	0.987 (2)	0.0010 (13)	0.825 (2)	0.057*
H1D	0.853 (3)	0.0434 (14)	0.8685 (19)	0.057*
O4	0.68389 (15)	0.39253 (7)	1.05383 (12)	0.0300 (3)
H4A	0.757 (3)	0.4174 (13)	1.136 (3)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0257 (7)	0.0190 (7)	0.0174 (7)	0.0003 (5)	0.0030 (6)	−0.0014 (5)
C2	0.0206 (7)	0.0246 (7)	0.0197 (8)	−0.0019 (6)	0.0061 (6)	0.0011 (6)
C3	0.0197 (7)	0.0212 (7)	0.0184 (7)	−0.0010 (5)	0.0070 (6)	0.0002 (5)
C4	0.0184 (7)	0.0224 (7)	0.0181 (7)	0.0003 (5)	0.0067 (5)	0.0004 (5)
C5	0.0193 (7)	0.0224 (7)	0.0180 (7)	0.0006 (5)	0.0060 (5)	0.0014 (5)
C6	0.0185 (7)	0.0214 (7)	0.0183 (7)	0.0006 (5)	0.0067 (6)	0.0002 (5)
C7	0.0234 (7)	0.0226 (7)	0.0225 (8)	0.0031 (6)	0.0059 (6)	0.0028 (6)
C8	0.0210 (7)	0.0319 (8)	0.0197 (7)	0.0040 (6)	0.0006 (6)	0.0032 (6)
C9	0.0231 (7)	0.0326 (8)	0.0209 (7)	−0.0040 (6)	0.0022 (6)	−0.0049 (6)
C10	0.0280 (8)	0.0223 (7)	0.0251 (8)	−0.0034 (6)	0.0068 (6)	−0.0021 (6)
C11	0.0224 (7)	0.0183 (7)	0.0199 (8)	0.0001 (5)	0.0087 (6)	0.0007 (5)
O1	0.0256 (5)	0.0411 (6)	0.0285 (6)	0.0120 (5)	0.0063 (4)	0.0085 (5)
O2	0.0345 (6)	0.0186 (5)	0.0198 (5)	0.0016 (4)	0.0092 (4)	0.0012 (4)
O3	0.0391 (6)	0.0319 (6)	0.0220 (6)	−0.0069 (5)	−0.0061 (5)	0.0050 (5)
N1	0.0240 (6)	0.0173 (6)	0.0193 (6)	0.0012 (5)	0.0050 (5)	0.0010 (4)
O1W	0.0426 (7)	0.0441 (7)	0.0249 (6)	0.0210 (5)	0.0073 (5)	0.0095 (5)
O4	0.0367 (6)	0.0217 (5)	0.0243 (6)	−0.0046 (4)	−0.0011 (5)	−0.0029 (4)

C1—O1	1.2439 (17)	C6—C7	1.4170 (18)
C1—O2	1.2470 (17)	C7—C8	1.359 (2)
C1—C4	1.5310 (18)	C7—H7	0.9300
C2—O3	1.2038 (16)	C8—C9	1.411 (2)
C2—O4	1.3184 (17)	C8—H8	0.9300
C2—C3	1.4929 (18)	C9—C10	1.369 (2)
C3—C11	1.3727 (18)	C9—H9	0.9300
C3—C4	1.4098 (19)	C10—H10	0.9300
C4—N1	1.3260 (17)	C11—H11	0.9300
C5—N1	1.3741 (17)	N1—H1A	0.93 (2)
C5—C10	1.4059 (19)	O1W—H1C	0.858 (15)
C5—C6	1.409 (2)	O1W—H1D	0.868 (15)
C6—C11	1.4126 (19)	O4—H4A	0.89 (2)
O1—C1—O2	128.49 (13)	C8—C7—H7	120.0
O1—C1—C4	115.97 (12)	C6—C7—H7	120.0
O2—C1—C4	115.32 (11)	C7—C8—C9	120.75 (13)
O3—C2—O4	124.70 (13)	C7—C8—H8	119.6
O3—C2—C3	121.96 (12)	C9—C8—H8	119.6
O4—C2—C3	113.32 (12)	C10—C9—C8	121.03 (13)
C11—C3—C4	118.97 (12)	C10—C9—H9	119.5
C11—C3—C2	122.18 (12)	C8—C9—H9	119.5
C4—C3—C2	118.81 (11)	C9—C10—C5	118.53 (13)
N1—C4—C3	119.43 (11)	C9—C10—H10	120.7
N1—C4—C1	114.47 (11)	C5—C10—H10	120.7
C3—C4—C1	126.09 (11)	C3—C11—C6	121.18 (13)
N1—C5—C10	120.37 (13)	C3—C11—H11	119.4
N1—C5—C6	118.34 (12)	C6—C11—H11	119.4
C10—C5—C6	121.29 (12)	C4—N1—C5	123.95 (12)
C5—C6—C11	118.10 (12)	C4—N1—H1A	118.0 (11)
C5—C6—C7	118.30 (12)	C5—N1—H1A	118.0 (11)
C11—C6—C7	123.60 (13)	H1C—O1W—H1D	104.2 (18)
C8—C7—C6	120.10 (13)	C2—O4—H4A	109.7 (13)
O3—C2—C3—C11	170.11 (13)	C5—C6—C7—C8	−0.28 (18)
O4—C2—C3—C11	−8.67 (17)	C11—C6—C7—C8	179.25 (13)
O3—C2—C3—C4	−7.72 (19)	C6—C7—C8—C9	−0.4 (2)
O4—C2—C3—C4	173.51 (12)	C7—C8—C9—C10	0.4 (2)
C11—C3—C4—N1	1.20 (18)	C8—C9—C10—C5	0.2 (2)
C2—C3—C4—N1	179.10 (11)	N1—C5—C10—C9	179.13 (12)
C11—C3—C4—C1	−178.47 (11)	C6—C5—C10—C9	−0.88 (19)
C2—C3—C4—C1	−0.57 (18)	C4—C3—C11—C6	−0.89 (18)
O1—C1—C4—N1	89.54 (14)	C2—C3—C11—C6	−178.72 (12)
O2—C1—C4—N1	−85.51 (14)	C5—C6—C11—C3	−0.38 (18)
O1—C1—C4—C3	−90.78 (16)	C7—C6—C11—C3	−179.91 (12)
O2—C1—C4—C3	94.17 (15)	C3—C4—N1—C5	−0.20 (18)
N1—C5—C6—C11	1.36 (18)	C1—C4—N1—C5	179.51 (11)
C10—C5—C6—C11	−178.63 (11)	C10—C5—N1—C4	178.89 (12)
N1—C5—C6—C7	−179.09 (11)	C6—C5—N1—C4	−1.10 (18)
C10—C5—C6—C7	0.92 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.93 (2)	1.71 (2)	2.6392 (16)	170.7 (17)
O1W—H1C···O1ii	0.86 (2)	1.93 (2)	2.7589 (16)	161 (2)
O4—H4A···O1Wiii	0.89 (2)	1.70 (2)	2.5950 (17)	175.6 (19)
O1W—H1D···O1	0.87 (2)	1.90 (2)	2.7597 (16)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.93 (2)	1.71 (2)	2.6392 (16)	170.7 (17)
O1W—H1C⋯O1ii	0.86 (2)	1.93 (2)	2.7589 (16)	161 (2)
O1W—H1D⋯O1	0.87 (2)	1.90 (2)	2.7597 (16)	175 (2)
O4—H4A⋯O1Wiii	0.89 (2)	1.70 (2)	2.5950 (17)	175.6 (19)

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