Crystal structure of quinolinium 2-carboxy-6-nitro-benzoate monohydrate.

In the anion of the title hydrated mol-ecular salt, C9H8N(+)·C8H4NO6 (-)·H2O, the protonated carboxyl and nitro groups makes dihedral angles of 27.56 (5) and 6.86 (8)°, respectively, with the attached benzene ring, whereas the deprotonated carb-oxy group is almost orthogonal to it with a dihedral angle of 80.21 (1)°. In the crystal, the components are linked by O-H⋯O and N-H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by weak C-H⋯N and C-H⋯O inter-actions as well as aromatic π-π stacking [centroid-to-centroid distances: 3.7023 (8) & 3.6590 (9)Å] inter-actions, resulting 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 ▸); Divya Bharathi et al. (2015 ▸).

Experimental

Crystal data

C9H8N+·C8H4NO6 −·H2O

M = 358.30

Monoclinic,

a = 14.7622 (8) Å

b = 14.2461 (8) Å

c = 7.6395 (4) Å

β = 104.434 (2)°

V = 1555.90 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.26 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.969, T max = 0.979

32650 measured reflections

4728 independent reflections

3394 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.04

4728 reflections

248 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; 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/S2056989015006052/hb7390sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006052/hb7390Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006052/hb7390Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006052/hb7390fig1.tif

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

Click here for additional data file.

. DOI: 10.1107/S2056989015006052/hb7390fig2.tif

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

CCDC reference: 1015219

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

C9H8N+·C8H4NO6−·H2O	F(000) = 744
Mr = 358.30	Dx = 1.530 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9970 reflections
a = 14.7622 (8) Å	θ = 2.8–30.4°
b = 14.2461 (8) Å	µ = 0.12 mm−1
c = 7.6395 (4) Å	T = 295 K
β = 104.434 (2)°	Block, colourless
V = 1555.90 (15) Å3	0.26 × 0.24 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4728 independent reflections
Radiation source: fine-focus sealed tube	3394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 30.8°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
Tmin = 0.969, Tmax = 0.979	k = −20→20
32650 measured reflections	l = −10→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.4484P] where P = (Fo2 + 2Fc2)/3
4728 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.29 e Å−3
4 restraints	Δρmin = −0.20 e Å−3

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	0.64273 (8)	0.07483 (8)	−0.05905 (16)	0.0309 (2)
C2	0.57907 (9)	0.14414 (9)	−0.04652 (19)	0.0386 (3)
H2	0.5629	0.1900	−0.1354	0.046*
C3	0.54012 (9)	0.14429 (9)	0.09892 (19)	0.0405 (3)
H3	0.4982	0.1912	0.1106	0.049*
C4	0.56333 (9)	0.07465 (9)	0.22753 (18)	0.0361 (3)
H4	0.5351	0.0735	0.3236	0.043*
C5	0.62851 (8)	0.00608 (8)	0.21529 (16)	0.0295 (2)
C6	0.67125 (8)	0.00565 (8)	0.07151 (15)	0.0276 (2)
C7	0.65254 (8)	−0.06752 (8)	0.35872 (16)	0.0321 (2)
C8	0.74316 (8)	−0.06939 (8)	0.06354 (16)	0.0305 (2)
C9	0.95815 (10)	0.39076 (10)	0.1010 (2)	0.0450 (3)
H9	0.9905	0.4451	0.1463	0.054*
C10	0.87001 (11)	0.39591 (13)	−0.0086 (2)	0.0563 (4)
H10	0.8421	0.4543	−0.0379	0.068*
C11	0.82119 (11)	0.31475 (15)	−0.0772 (2)	0.0617 (5)
H11	0.7610	0.3196	−0.1515	0.074*
C12	0.86022 (10)	0.22927 (13)	−0.0373 (2)	0.0552 (4)
H12	0.8268	0.1759	−0.0848	0.066*
C13	0.95129 (9)	0.22011 (10)	0.07584 (19)	0.0387 (3)
C14	0.99619 (11)	0.13384 (10)	0.1225 (2)	0.0488 (4)
H14	0.9653	0.0784	0.0797	0.059*
C15	1.08465 (11)	0.13063 (10)	0.2302 (2)	0.0497 (4)
H15	1.1152	0.0734	0.2584	0.060*
C16	1.12878 (9)	0.21365 (10)	0.2974 (2)	0.0429 (3)
H16	1.1887	0.2117	0.3734	0.051*
C17	0.99937 (8)	0.30253 (9)	0.14427 (17)	0.0331 (3)
N1	0.67819 (8)	0.07495 (8)	−0.22213 (15)	0.0389 (3)
H2A	1.1177 (11)	0.3480 (9)	0.304 (2)	0.060 (5)*
N2	1.08727 (7)	0.29511 (8)	0.25544 (16)	0.0364 (2)
O1	0.58421 (7)	−0.08353 (8)	0.43610 (14)	0.0457 (2)
H1A	0.6007 (14)	−0.1247 (11)	0.516 (2)	0.069*
O2	0.72664 (7)	−0.10794 (7)	0.39726 (13)	0.0445 (2)
O3	0.82733 (6)	−0.04668 (7)	0.11938 (14)	0.0408 (2)
O4	0.71315 (7)	−0.14892 (6)	0.01135 (13)	0.0386 (2)
O5	0.65803 (10)	0.14023 (9)	−0.32691 (17)	0.0659 (4)
O6	0.72700 (9)	0.01019 (9)	−0.24593 (16)	0.0611 (3)
O7	0.62094 (7)	−0.21451 (7)	−0.32298 (13)	0.0420 (2)
H7A	0.6537 (12)	−0.1934 (13)	−0.2261 (17)	0.063*
H7B	0.6482 (12)	−0.2591 (10)	−0.359 (2)	0.063*

	U11	U22	U33	U12	U13	U23
C1	0.0293 (5)	0.0308 (6)	0.0300 (6)	−0.0029 (4)	0.0026 (4)	0.0001 (4)
C2	0.0368 (6)	0.0332 (6)	0.0406 (7)	0.0043 (5)	0.0001 (5)	0.0069 (5)
C3	0.0350 (6)	0.0363 (7)	0.0469 (8)	0.0107 (5)	0.0042 (5)	−0.0002 (5)
C4	0.0322 (6)	0.0386 (6)	0.0368 (6)	0.0049 (5)	0.0073 (5)	−0.0027 (5)
C5	0.0273 (5)	0.0287 (5)	0.0296 (6)	0.0008 (4)	0.0014 (4)	−0.0015 (4)
C6	0.0245 (5)	0.0256 (5)	0.0300 (6)	−0.0016 (4)	0.0017 (4)	−0.0027 (4)
C7	0.0341 (6)	0.0325 (6)	0.0281 (6)	0.0010 (5)	0.0047 (5)	−0.0021 (5)
C8	0.0328 (6)	0.0293 (5)	0.0290 (6)	0.0023 (4)	0.0068 (4)	−0.0014 (4)
C9	0.0443 (7)	0.0386 (7)	0.0511 (8)	0.0053 (6)	0.0100 (6)	0.0017 (6)
C10	0.0489 (9)	0.0593 (10)	0.0580 (10)	0.0201 (7)	0.0085 (7)	0.0066 (8)
C11	0.0353 (7)	0.0846 (13)	0.0584 (10)	0.0099 (8)	−0.0011 (7)	−0.0028 (9)
C12	0.0359 (7)	0.0647 (10)	0.0604 (10)	−0.0080 (7)	0.0031 (7)	−0.0138 (8)
C13	0.0316 (6)	0.0414 (7)	0.0437 (7)	−0.0041 (5)	0.0105 (5)	−0.0058 (6)
C14	0.0479 (8)	0.0350 (7)	0.0644 (10)	−0.0077 (6)	0.0157 (7)	−0.0050 (6)
C15	0.0469 (8)	0.0350 (7)	0.0684 (10)	0.0049 (6)	0.0166 (7)	0.0093 (7)
C16	0.0311 (6)	0.0444 (7)	0.0519 (8)	0.0019 (5)	0.0080 (6)	0.0107 (6)
C17	0.0282 (5)	0.0364 (6)	0.0355 (6)	−0.0006 (5)	0.0094 (5)	0.0014 (5)
N1	0.0401 (6)	0.0412 (6)	0.0338 (6)	−0.0060 (5)	0.0061 (5)	0.0015 (5)
N2	0.0289 (5)	0.0362 (5)	0.0429 (6)	−0.0049 (4)	0.0068 (4)	0.0021 (5)
O1	0.0425 (5)	0.0521 (6)	0.0446 (6)	0.0056 (4)	0.0148 (4)	0.0143 (4)
O2	0.0439 (5)	0.0486 (6)	0.0404 (5)	0.0147 (4)	0.0095 (4)	0.0113 (4)
O3	0.0286 (4)	0.0385 (5)	0.0539 (6)	0.0020 (4)	0.0078 (4)	−0.0039 (4)
O4	0.0459 (5)	0.0293 (4)	0.0388 (5)	0.0001 (4)	0.0071 (4)	−0.0059 (4)
O5	0.0789 (9)	0.0694 (8)	0.0530 (7)	0.0109 (6)	0.0232 (6)	0.0290 (6)
O6	0.0824 (9)	0.0594 (7)	0.0506 (6)	0.0141 (6)	0.0338 (6)	0.0025 (5)
O7	0.0478 (6)	0.0417 (5)	0.0355 (5)	0.0014 (4)	0.0086 (4)	0.0010 (4)

C1—C2	1.3828 (17)	C10—H10	0.9300
C1—C6	1.3907 (16)	C11—C12	1.349 (3)
C1—N1	1.4666 (16)	C11—H11	0.9300
C2—C3	1.372 (2)	C12—C13	1.4114 (19)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.3780 (19)	C13—C14	1.400 (2)
C3—H3	0.9300	C13—C17	1.4039 (18)
C4—C5	1.3906 (16)	C14—C15	1.360 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.3965 (17)	C15—C16	1.386 (2)
C5—C7	1.4940 (16)	C15—H15	0.9300
C6—C8	1.5184 (16)	C16—N2	1.3141 (17)
C7—O2	1.2060 (15)	C16—H16	0.9300
C7—O1	1.3101 (16)	C17—N2	1.3663 (16)
C8—O4	1.2453 (14)	N1—O6	1.2120 (16)
C8—O3	1.2516 (14)	N1—O5	1.2146 (15)
C9—C10	1.362 (2)	N2—H2A	0.908 (9)
C9—C17	1.3996 (19)	O1—H1A	0.840 (9)
C9—H9	0.9300	O7—H7A	0.833 (9)
C10—C11	1.394 (3)	O7—H7B	0.836 (9)
C2—C1—C6	123.08 (12)	C12—C11—C10	120.79 (14)
C2—C1—N1	116.78 (11)	C12—C11—H11	119.6
C6—C1—N1	120.12 (11)	C10—C11—H11	119.6
C3—C2—C1	119.09 (12)	C11—C12—C13	120.66 (15)
C3—C2—H2	120.5	C11—C12—H12	119.7
C1—C2—H2	120.5	C13—C12—H12	119.7
C2—C3—C4	119.75 (12)	C14—C13—C17	118.44 (12)
C2—C3—H3	120.1	C14—C13—C12	123.75 (13)
C4—C3—H3	120.1	C17—C13—C12	117.82 (13)
C3—C4—C5	120.73 (12)	C15—C14—C13	120.41 (13)
C3—C4—H4	119.6	C15—C14—H14	119.8
C5—C4—H4	119.6	C13—C14—H14	119.8
C4—C5—C6	120.78 (11)	C14—C15—C16	119.16 (13)
C4—C5—C7	119.05 (11)	C14—C15—H15	120.4
C6—C5—C7	120.17 (10)	C16—C15—H15	120.4
C1—C6—C5	116.47 (10)	N2—C16—C15	121.06 (12)
C1—C6—C8	124.05 (11)	N2—C16—H16	119.5
C5—C6—C8	119.47 (10)	C15—C16—H16	119.5
O2—C7—O1	124.07 (12)	N2—C17—C9	120.40 (12)
O2—C7—C5	123.32 (11)	N2—C17—C13	118.71 (11)
O1—C7—C5	112.60 (10)	C9—C17—C13	120.89 (12)
O4—C8—O3	126.02 (11)	O6—N1—O5	122.75 (13)
O4—C8—C6	117.19 (10)	O6—N1—C1	118.55 (11)
O3—C8—C6	116.67 (10)	O5—N1—C1	118.69 (12)
C10—C9—C17	119.08 (14)	C16—N2—C17	122.19 (11)
C10—C9—H9	120.5	C16—N2—H2A	118.7 (12)
C17—C9—H9	120.5	C17—N2—H2A	119.1 (12)
C9—C10—C11	120.77 (15)	C7—O1—H1A	109.7 (14)
C9—C10—H10	119.6	H7A—O7—H7B	110.4 (18)
C11—C10—H10	119.6
C6—C1—C2—C3	−1.47 (19)	C17—C9—C10—C11	−0.1 (3)
N1—C1—C2—C3	176.70 (11)	C9—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	−1.4 (2)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—C5	2.4 (2)	C11—C12—C13—C14	−179.82 (16)
C3—C4—C5—C6	−0.64 (18)	C11—C12—C13—C17	−0.1 (2)
C3—C4—C5—C7	179.28 (12)	C17—C13—C14—C15	−0.7 (2)
C2—C1—C6—C5	3.15 (17)	C12—C13—C14—C15	179.01 (16)
N1—C1—C6—C5	−174.97 (10)	C13—C14—C15—C16	1.9 (2)
C2—C1—C6—C8	−178.10 (11)	C14—C15—C16—N2	−1.5 (2)
N1—C1—C6—C8	3.78 (17)	C10—C9—C17—N2	−179.26 (14)
C4—C5—C6—C1	−2.06 (16)	C10—C9—C17—C13	0.3 (2)
C7—C5—C6—C1	178.02 (10)	C14—C13—C17—N2	−0.92 (19)
C4—C5—C6—C8	179.13 (11)	C12—C13—C17—N2	179.37 (13)
C7—C5—C6—C8	−0.78 (16)	C14—C13—C17—C9	179.54 (14)
C4—C5—C7—O2	−153.38 (13)	C12—C13—C17—C9	−0.2 (2)
C6—C5—C7—O2	26.54 (18)	C2—C1—N1—O6	−173.03 (12)
C4—C5—C7—O1	27.15 (16)	C6—C1—N1—O6	5.20 (17)
C6—C5—C7—O1	−152.93 (11)	C2—C1—N1—O5	7.53 (17)
C1—C6—C8—O4	−100.90 (14)	C6—C1—N1—O5	−174.24 (12)
C5—C6—C8—O4	77.82 (14)	C15—C16—N2—C17	−0.1 (2)
C1—C6—C8—O3	82.81 (15)	C9—C17—N2—C16	−179.12 (13)
C5—C6—C8—O3	−98.48 (13)	C13—C17—N2—C16	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4	0.83 (1)	1.92 (1)	2.7416 (14)	171 (19)
O7—H7B···O4i	0.84 (1)	2.02 (1)	2.8459 (14)	169 (18)
O1—H1A···O7ii	0.84 (1)	1.75 (1)	2.5818 (14)	173 (2)
N2—H2A···O3iii	0.91 (1)	1.74 (1)	2.6425 (14)	176 (18)
C16—H16···O4iii	0.93	2.49	3.1166 (17)	125
C16—H16···O2iv	0.93	2.39	3.1278 (17)	136
C12—H12···N1	0.93	2.61	3.4866 (19)	157

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O7H7AO4	0.83(1)	1.92(1)	2.7416(14)	171(19)
O7H7BO4i	0.84(1)	2.02(1)	2.8459(14)	169(18)
O1H1AO7ii	0.84(1)	1.75(1)	2.5818(14)	173(2)
N2H2AO3iii	0.91(1)	1.74(1)	2.6425(14)	176(18)
C16H16O4iii	0.93	2.49	3.1166(17)	125
C16H16O2iv	0.93	2.39	3.1278(17)	136
C12H12N1	0.93	2.61	3.4866(19)	157

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