Crystal structure of 8-hy-droxy-quinolin-ium 2-carboxy-6-nitro-benzoate mono-hydrate.

In the title hydrated salt, C9H8NO(+)·C8H4NO6 (-)·H2O, the deprotonated carboxyl-ate group is almost normal to its attached benzene ring [dihedral angle = 83.56 (8)°], whereas the protonated carboxyl-ate group is close to parallel [dihedral angle = 24.56 (9)°]. In the crystal, the components are linked by N-H⋯O and O-H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by C-H⋯O and π-π [centroid-to-centroid distances = 3.6408 (9) and 3.6507 (9) Å] inter-actions, which result in a three-dimensional network.

Related literature

For the biological activity of quinoline derivatives, see: Font et al. (1997 ▸); Sloboda et al. (1991 ▸). For similar structures, see: Castañeda et al. (2014 ▸); Kafka et al. (2012 ▸); Li & Chai (2007 ▸).

Experimental

Crystal data

C9H8NO+·C8H4n class="Chemical">NO6 −·H2O

M = 374.30

Monoclinic,

a = 14.4283 (5) Å

b = 13.8196 (5) Å

c = 8.0483 (3) Å

β = 101.441 (2)°

V = 1572.89 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 295 K

0.26 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.968, T max = 0.977

58922 measured reflections

7431 independent reflections

4272 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.176

S = 1.02

7431 reflections

260 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500571X/hb7385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500571X/hb7385Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500571X/hb7385Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500571X/hb7385fig1.tif

The mol­ecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

c . DOI: 10.1107/S205698901500571X/hb7385fig2.tif

The packing of (I), viewed down c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

CCDC reference: 1055171

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H8NO+·C8H4NO6−·H2O	F(000) = 776
Mr = 374.30	Dx = 1.581 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9900 reflections
a = 14.4283 (5) Å	θ = 2.8–33.4°
b = 13.8196 (5) Å	µ = 0.13 mm−1
c = 8.0483 (3) Å	T = 295 K
β = 101.441 (2)°	Block, colourless
V = 1572.89 (10) Å3	0.26 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	7431 independent reflections
Radiation source: fine-focus sealed tube	4272 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 36.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.968, Tmax = 0.977	k = −19→22
58922 measured reflections	l = −13→12

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.9848P] where P = (Fo2 + 2Fc2)/3
7431 reflections	(Δ/σ)max < 0.001
260 parameters	Δρmax = 0.50 e Å−3
5 restraints	Δρmin = −0.38 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	0.17265 (9)	0.48978 (9)	0.55989 (18)	0.0237 (2)
C2	0.13410 (10)	0.48988 (10)	0.70682 (19)	0.0262 (3)
C3	0.06506 (11)	0.42272 (12)	0.7270 (2)	0.0331 (3)
H3	0.0403	0.4238	0.8252	0.040*
C4	0.03290 (11)	0.35481 (12)	0.6037 (2)	0.0370 (4)
H4	−0.0117	0.3091	0.6203	0.044*
C5	0.06716 (11)	0.35508 (12)	0.4557 (2)	0.0339 (3)
H5	0.0449	0.3108	0.3702	0.041*
C6	0.13531 (10)	0.42230 (10)	0.43632 (19)	0.0267 (3)
C7	0.24827 (10)	0.56315 (10)	0.53939 (18)	0.0249 (3)
C8	0.16432 (11)	0.56359 (11)	0.84160 (19)	0.0294 (3)
C9	0.46422 (11)	0.34368 (10)	0.87844 (19)	0.0288 (3)
C10	0.53122 (13)	0.40133 (12)	0.8201 (2)	0.0377 (4)
H10	0.5225	0.4680	0.8125	0.045*
C11	0.60883 (13)	0.36137 (14)	0.7744 (2)	0.0424 (4)
H11	0.6521	0.4002	0.7341	0.051*
C12	0.62252 (11)	0.26245 (14)	0.7886 (2)	0.0390 (4)
H12	0.6752	0.2346	0.7575	0.047*
C13	0.48139 (9)	0.24333 (10)	0.89029 (18)	0.0247 (3)
C14	0.41699 (10)	0.18003 (10)	0.94525 (19)	0.0284 (3)
C15	0.33963 (11)	0.21885 (13)	0.9934 (2)	0.0364 (3)
H15	0.2978	0.1785	1.0346	0.044*
C16	0.32192 (13)	0.31850 (15)	0.9818 (2)	0.0432 (4)
H16	0.2680	0.3428	1.0140	0.052*
C17	0.38181 (13)	0.38061 (12)	0.9246 (2)	0.0390 (4)
H17	0.3685	0.4465	0.9160	0.047*
N1	0.16655 (10)	0.42040 (10)	0.27386 (18)	0.0337 (3)
N2	0.56126 (9)	0.20732 (9)	0.84612 (17)	0.0305 (3)
H2	0.5741 (15)	0.1450 (8)	0.866 (3)	0.047 (6)*
O1	0.22455 (12)	0.47889 (11)	0.24810 (18)	0.0545 (4)
O2	0.13344 (13)	0.35960 (13)	0.1701 (2)	0.0684 (5)
O3	0.33312 (7)	0.53639 (8)	0.57868 (15)	0.0318 (2)
O4	0.22067 (8)	0.64521 (8)	0.49029 (15)	0.0326 (2)
O5	0.09894 (10)	0.57856 (11)	0.93152 (18)	0.0465 (3)
H5A	0.1152 (18)	0.6216 (15)	1.002 (3)	0.070*
O6	0.23875 (9)	0.60562 (10)	0.86357 (17)	0.0435 (3)
O7	0.43930 (9)	0.08565 (8)	0.94455 (17)	0.0378 (3)
H7	0.3990 (13)	0.0519 (15)	0.981 (3)	0.057*
O8	0.13275 (9)	0.78915 (10)	0.66412 (16)	0.0392 (3)
H8A	0.1644 (15)	0.8061 (18)	0.7569 (18)	0.059*
H8B	0.1616 (16)	0.7423 (13)	0.635 (3)	0.059*

	U11	U22	U33	U12	U13	U23
C1	0.0214 (5)	0.0215 (5)	0.0289 (6)	0.0023 (4)	0.0070 (5)	0.0021 (5)
C2	0.0244 (6)	0.0266 (6)	0.0286 (7)	0.0001 (5)	0.0074 (5)	0.0023 (5)
C3	0.0308 (7)	0.0365 (8)	0.0344 (8)	−0.0042 (6)	0.0123 (6)	0.0047 (6)
C4	0.0300 (7)	0.0364 (8)	0.0457 (9)	−0.0096 (6)	0.0101 (7)	0.0028 (7)
C5	0.0298 (7)	0.0321 (7)	0.0395 (8)	−0.0067 (6)	0.0064 (6)	−0.0041 (6)
C6	0.0244 (6)	0.0262 (6)	0.0304 (7)	0.0012 (5)	0.0076 (5)	−0.0007 (5)
C7	0.0269 (6)	0.0238 (6)	0.0262 (6)	−0.0013 (5)	0.0109 (5)	−0.0016 (5)
C8	0.0323 (7)	0.0301 (7)	0.0269 (7)	0.0003 (5)	0.0084 (5)	0.0024 (5)
C9	0.0337 (7)	0.0212 (6)	0.0294 (7)	0.0003 (5)	0.0014 (5)	0.0015 (5)
C10	0.0465 (9)	0.0239 (7)	0.0395 (8)	−0.0065 (6)	0.0006 (7)	0.0066 (6)
C11	0.0365 (8)	0.0441 (9)	0.0449 (10)	−0.0124 (7)	0.0041 (7)	0.0152 (8)
C12	0.0267 (7)	0.0467 (9)	0.0441 (9)	−0.0008 (6)	0.0088 (6)	0.0120 (7)
C13	0.0249 (6)	0.0221 (6)	0.0264 (6)	−0.0004 (4)	0.0034 (5)	0.0023 (5)
C14	0.0289 (7)	0.0256 (6)	0.0303 (7)	−0.0042 (5)	0.0052 (5)	0.0017 (5)
C15	0.0316 (7)	0.0420 (9)	0.0371 (8)	−0.0043 (6)	0.0103 (6)	0.0004 (7)
C16	0.0377 (8)	0.0510 (10)	0.0427 (9)	0.0119 (7)	0.0126 (7)	−0.0041 (8)
C17	0.0446 (9)	0.0305 (7)	0.0415 (9)	0.0111 (7)	0.0072 (7)	−0.0023 (7)
N1	0.0339 (7)	0.0353 (7)	0.0334 (7)	−0.0031 (5)	0.0103 (5)	−0.0067 (5)
N2	0.0281 (6)	0.0267 (6)	0.0368 (7)	0.0031 (4)	0.0069 (5)	0.0071 (5)
O1	0.0734 (10)	0.0545 (8)	0.0431 (7)	−0.0271 (7)	0.0301 (7)	−0.0107 (6)
O2	0.0782 (11)	0.0794 (12)	0.0555 (9)	−0.0402 (9)	0.0328 (8)	−0.0384 (8)
O3	0.0249 (5)	0.0287 (5)	0.0439 (6)	0.0004 (4)	0.0122 (4)	−0.0032 (4)
O4	0.0375 (6)	0.0241 (5)	0.0365 (6)	0.0007 (4)	0.0084 (5)	0.0031 (4)
O5	0.0434 (7)	0.0575 (8)	0.0442 (7)	−0.0089 (6)	0.0222 (6)	−0.0169 (6)
O6	0.0428 (7)	0.0496 (7)	0.0410 (7)	−0.0147 (6)	0.0153 (5)	−0.0122 (6)
O7	0.0393 (6)	0.0232 (5)	0.0537 (7)	−0.0050 (4)	0.0161 (5)	0.0044 (5)
O8	0.0429 (7)	0.0397 (7)	0.0361 (6)	0.0043 (5)	0.0104 (5)	0.0014 (5)

C1—C6	1.392 (2)	C11—C12	1.383 (3)
C1—C2	1.4030 (19)	C11—H11	0.9300
C1—C7	1.5222 (18)	C12—N2	1.318 (2)
C2—C3	1.394 (2)	C12—H12	0.9300
C2—C8	1.489 (2)	C13—N2	1.3655 (18)
C3—C4	1.378 (2)	C13—C14	1.4097 (19)
C3—H3	0.9300	C14—O7	1.3437 (18)
C4—C5	1.377 (2)	C14—C15	1.362 (2)
C4—H4	0.9300	C15—C16	1.400 (3)
C5—C6	1.384 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.362 (3)
C6—N1	1.4654 (19)	C16—H16	0.9300
C7—O4	1.2404 (17)	C17—H17	0.9300
C7—O3	1.2577 (17)	N1—O1	1.2106 (18)
C8—O6	1.2028 (19)	N1—O2	1.2137 (19)
C8—O5	1.3142 (19)	N2—H2	0.889 (9)
C9—C10	1.403 (2)	O5—H5A	0.823 (10)
C9—C13	1.4085 (19)	O7—H7	0.841 (9)
C9—C17	1.410 (2)	O8—H8A	0.828 (10)
C10—C11	1.363 (3)	O8—H8B	0.829 (10)
C10—H10	0.9300
C6—C1—C2	116.16 (12)	C10—C11—C12	119.32 (15)
C6—C1—C7	123.58 (12)	C10—C11—H11	120.3
C2—C1—C7	120.21 (12)	C12—C11—H11	120.3
C3—C2—C1	120.61 (14)	N2—C12—C11	120.37 (16)
C3—C2—C8	118.90 (13)	N2—C12—H12	119.8
C1—C2—C8	120.46 (12)	C11—C12—H12	119.8
C4—C3—C2	121.06 (14)	N2—C13—C9	119.16 (13)
C4—C3—H3	119.5	N2—C13—C14	119.89 (13)
C2—C3—H3	119.5	C9—C13—C14	120.94 (13)
C5—C4—C3	119.59 (14)	O7—C14—C15	126.44 (14)
C5—C4—H4	120.2	O7—C14—C13	115.32 (13)
C3—C4—H4	120.2	C15—C14—C13	118.23 (14)
C4—C5—C6	118.98 (15)	C14—C15—C16	121.17 (15)
C4—C5—H5	120.5	C14—C15—H15	119.4
C6—C5—H5	120.5	C16—C15—H15	119.4
C5—C6—C1	123.52 (14)	C17—C16—C15	121.51 (16)
C5—C6—N1	116.10 (13)	C17—C16—H16	119.2
C1—C6—N1	120.38 (12)	C15—C16—H16	119.2
O4—C7—O3	125.72 (13)	C16—C17—C9	119.08 (15)
O4—C7—C1	116.86 (12)	C16—C17—H17	120.5
O3—C7—C1	117.37 (12)	C9—C17—H17	120.5
O6—C8—O5	124.10 (15)	O1—N1—O2	122.38 (15)
O6—C8—C2	124.14 (14)	O1—N1—C6	119.10 (13)
O5—C8—C2	111.75 (13)	O2—N1—C6	118.52 (14)
C10—C9—C13	117.26 (14)	C12—N2—C13	122.68 (14)
C10—C9—C17	123.74 (14)	C12—N2—H2	119.6 (14)
C13—C9—C17	119.00 (14)	C13—N2—H2	117.5 (14)
C11—C10—C9	121.17 (15)	C8—O5—H5A	110.8 (19)
C11—C10—H10	119.4	C14—O7—H7	110.7 (17)
C9—C10—H10	119.4	H8A—O8—H8B	105 (2)
C6—C1—C2—C3	2.4 (2)	C9—C10—C11—C12	−1.1 (3)
C7—C1—C2—C3	−179.76 (13)	C10—C11—C12—N2	−0.1 (3)
C6—C1—C2—C8	−175.78 (13)	C10—C9—C13—N2	0.3 (2)
C7—C1—C2—C8	2.0 (2)	C17—C9—C13—N2	−179.84 (14)
C1—C2—C3—C4	0.0 (2)	C10—C9—C13—C14	−179.04 (14)
C8—C2—C3—C4	178.20 (15)	C17—C9—C13—C14	0.8 (2)
C2—C3—C4—C5	−2.1 (3)	N2—C13—C14—O7	−2.0 (2)
C3—C4—C5—C6	1.7 (3)	C9—C13—C14—O7	177.38 (14)
C4—C5—C6—C1	0.8 (2)	N2—C13—C14—C15	177.96 (14)
C4—C5—C6—N1	−178.24 (15)	C9—C13—C14—C15	−2.7 (2)
C2—C1—C6—C5	−2.9 (2)	O7—C14—C15—C16	−177.32 (17)
C7—C1—C6—C5	179.40 (14)	C13—C14—C15—C16	2.8 (2)
C2—C1—C6—N1	176.16 (13)	C14—C15—C16—C17	−1.0 (3)
C7—C1—C6—N1	−1.6 (2)	C15—C16—C17—C9	−1.0 (3)
C6—C1—C7—O4	96.24 (16)	C10—C9—C17—C16	−179.12 (17)
C2—C1—C7—O4	−81.38 (17)	C13—C9—C17—C16	1.0 (2)
C6—C1—C7—O3	−85.96 (18)	C5—C6—N1—O1	178.42 (16)
C2—C1—C7—O3	96.42 (16)	C1—C6—N1—O1	−0.7 (2)
C3—C2—C8—O6	157.79 (16)	C5—C6—N1—O2	−2.0 (2)
C1—C2—C8—O6	−24.0 (2)	C1—C6—N1—O2	178.93 (17)
C3—C2—C8—O5	−23.5 (2)	C11—C12—N2—C13	1.5 (3)
C1—C2—C8—O5	154.77 (14)	C9—C13—N2—C12	−1.6 (2)
C13—C9—C10—C11	1.0 (2)	C14—C13—N2—C12	177.75 (15)
C17—C9—C10—C11	−178.83 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.89 (1)	2.00 (1)	2.8112 (16)	151 (2)
O5—H5A···O8ii	0.82 (1)	1.78 (1)	2.5928 (18)	171 (3)
O7—H7···O3iii	0.84 (1)	1.82 (1)	2.6482 (15)	168 (2)
O8—H8B···O4	0.83 (1)	2.07 (1)	2.8683 (17)	163 (2)
O8—H8A···O4ii	0.83 (1)	2.01 (1)	2.8288 (18)	170 (2)
C11—H11···O1iv	0.93	2.42	3.295 (2)	156
C12—H12···O6i	0.93	2.48	3.343 (2)	155
C16—H16···O2v	0.93	2.52	3.413 (2)	160

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2O3i	0.89(1)	2.00(1)	2.8112(16)	151(2)
O5H5AO8ii	0.82(1)	1.78(1)	2.5928(18)	171(3)
O7H7O3iii	0.84(1)	1.82(1)	2.6482(15)	168(2)
O8H8BO4	0.83(1)	2.07(1)	2.8683(17)	163(2)
O8H8AO4ii	0.83(1)	2.01(1)	2.8288(18)	170(2)
C11H11O1iv	0.93	2.42	3.295(2)	156
C12H12O6i	0.93	2.48	3.343(2)	155
C16H16O2v	0.93	2.52	3.413(2)	160

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