8-(Carboxy-methoxy)-quinolinium nitrate monohydrate.

In the title compound, C(11)H(10)NO(3) (+)·NO(3) (-)·H(2)O, the planar 8-carboxy-methoxy-quinolinium cation, the nitrate anion and the water mol-ecule are dimerized by hydrogen bonds into square building-block units, and then further assembled into two-dimensional gently undulating supra-molecular layers.

Related literature

For general background, see Czugler & Kalman (1981 ▶); Das et al. (1987 ▶); Song et al. (2004 ▶); Wang & Lu (2004 ▶).

Experimental

Crystal data

C11H10NO3 +·NO3 −·H2O

M = 284.23

Monoclinic,

a = 5.3577 (5) Å

b = 19.5100 (17) Å

c = 11.8959 (11) Å

β = 94.663 (3)°

V = 1239.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 (2) K

0.25 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.980

6235 measured reflections

2071 independent reflections

1376 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.01

2071 reflections

189 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1998 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808020357/rn2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020357/rn2043Isup2.hkl

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

C11H10NO3+·NO3–·H2O	F000 = 592
Mr = 284.23	Dx = 1.523 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1544 reflections
a = 5.3577 (5) Å	θ = 2.7–22.5º
b = 19.5100 (17) Å	µ = 0.13 mm−1
c = 11.8959 (11) Å	T = 298 (2) K
β = 94.663 (3)º	Block, yellow
V = 1239.3 (2) Å3	0.25 × 0.22 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2071 independent reflections
Radiation source: fine-focus sealed tube	1376 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 298(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.968, Tmax = 0.980	k = −23→22
6235 measured reflections	l = −14→13

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2071 reflections	Δρmax = 0.14 e Å−3
189 parameters	Δρmin = −0.16 e Å−3
3 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: 0.0044 (12)

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	0.3857 (3)	1.04106 (6)	0.31886 (12)	0.0504 (4)
O2	0.7769 (3)	1.08262 (7)	0.45561 (14)	0.0639 (5)
O3	0.6421 (3)	1.19011 (7)	0.44971 (15)	0.0717 (5)
H3	0.7765	1.1975	0.4856	0.107*
O4	0.7649 (4)	0.21455 (8)	0.17156 (19)	0.0945 (7)
O5	0.5562 (3)	0.28962 (8)	0.07269 (16)	0.0761 (6)
O6	0.4361 (4)	0.18475 (9)	0.07206 (17)	0.0943 (7)
O7	0.7613 (3)	0.94258 (8)	0.41435 (15)	0.0697 (5)
H7A	0.766 (4)	0.9861 (5)	0.420 (2)	0.105*
H7B	0.893 (3)	0.9224 (10)	0.439 (2)	0.105*
N1	0.3815 (3)	0.90790 (8)	0.26857 (14)	0.0478 (5)
H1	0.4942	0.9259	0.3150	0.057*
N2	0.5863 (4)	0.22855 (10)	0.10544 (17)	0.0595 (5)
C1	0.3960 (5)	0.84190 (10)	0.24671 (19)	0.0585 (6)
H1A	0.5251	0.8159	0.2820	0.070*
C2	0.2210 (5)	0.81128 (12)	0.1718 (2)	0.0678 (7)
H2	0.2335	0.7649	0.1552	0.081*
C3	0.0298 (5)	0.84926 (12)	0.1222 (2)	0.0633 (7)
H3A	−0.0890	0.8285	0.0719	0.076*
C4	0.0098 (4)	0.91954 (11)	0.14604 (17)	0.0491 (6)
C5	−0.1837 (5)	0.96193 (13)	0.09874 (19)	0.0597 (6)
H5	−0.3112	0.9434	0.0503	0.072*
C6	−0.1842 (5)	1.02966 (12)	0.12375 (19)	0.0592 (6)
H6	−0.3134	1.0571	0.0923	0.071*
C7	0.0059 (4)	1.05930 (11)	0.19611 (18)	0.0503 (6)
H7	0.0039	1.1062	0.2103	0.060*
C8	0.1930 (4)	1.01977 (9)	0.24550 (16)	0.0428 (5)
C9	0.1954 (4)	0.94906 (10)	0.22072 (16)	0.0415 (5)
C10	0.4012 (4)	1.11253 (9)	0.34252 (17)	0.0480 (6)
H10A	0.2518	1.1275	0.3764	0.058*
H10B	0.4137	1.1380	0.2732	0.058*
C11	0.6279 (4)	1.12555 (11)	0.42193 (17)	0.0482 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0499 (10)	0.0361 (7)	0.0612 (9)	0.0015 (7)	−0.0185 (8)	−0.0028 (6)
O2	0.0534 (11)	0.0450 (9)	0.0881 (11)	0.0037 (8)	−0.0256 (9)	−0.0097 (8)
O3	0.0775 (14)	0.0385 (8)	0.0930 (13)	−0.0001 (8)	−0.0295 (10)	−0.0109 (8)
O4	0.0822 (14)	0.0620 (11)	0.1291 (16)	0.0015 (10)	−0.0530 (13)	0.0185 (11)
O5	0.0753 (13)	0.0433 (9)	0.1048 (13)	0.0006 (8)	−0.0219 (10)	0.0184 (9)
O6	0.0987 (16)	0.0594 (10)	0.1156 (15)	−0.0244 (11)	−0.0464 (13)	0.0157 (10)
O7	0.0638 (12)	0.0514 (9)	0.0877 (12)	0.0058 (8)	−0.0320 (10)	−0.0014 (9)
N1	0.0471 (12)	0.0411 (10)	0.0533 (10)	−0.0052 (9)	−0.0074 (9)	0.0001 (8)
N2	0.0587 (14)	0.0471 (12)	0.0697 (13)	0.0000 (11)	−0.0124 (11)	0.0048 (10)
C1	0.0633 (17)	0.0381 (12)	0.0723 (15)	−0.0001 (11)	−0.0047 (14)	0.0011 (11)
C2	0.077 (2)	0.0438 (13)	0.0808 (17)	−0.0116 (13)	−0.0052 (15)	−0.0090 (12)
C3	0.0669 (18)	0.0577 (14)	0.0630 (15)	−0.0201 (13)	−0.0083 (14)	−0.0099 (12)
C4	0.0439 (14)	0.0542 (13)	0.0474 (12)	−0.0082 (11)	−0.0059 (11)	−0.0006 (10)
C5	0.0461 (16)	0.0749 (17)	0.0552 (14)	−0.0107 (13)	−0.0143 (12)	−0.0008 (12)
C6	0.0450 (15)	0.0719 (16)	0.0579 (14)	0.0072 (13)	−0.0120 (12)	0.0073 (12)
C7	0.0455 (15)	0.0474 (12)	0.0562 (13)	0.0041 (11)	−0.0061 (12)	0.0045 (10)
C8	0.0405 (14)	0.0433 (12)	0.0429 (11)	−0.0027 (10)	−0.0068 (11)	0.0010 (9)
C9	0.0361 (13)	0.0434 (11)	0.0437 (11)	−0.0018 (10)	−0.0038 (10)	0.0036 (9)
C10	0.0508 (15)	0.0347 (11)	0.0560 (13)	0.0005 (10)	−0.0102 (11)	0.0011 (9)
C11	0.0506 (15)	0.0400 (12)	0.0528 (13)	−0.0033 (11)	−0.0038 (11)	−0.0008 (10)

O1—C8	1.362 (2)	C2—H2	0.9300
O1—C10	1.424 (2)	C3—C4	1.406 (3)
O2—C11	1.203 (2)	C3—H3A	0.9300
O3—C11	1.303 (2)	C4—C9	1.402 (3)
O3—H3	0.8200	C4—C5	1.407 (3)
O4—N2	1.219 (2)	C5—C6	1.355 (3)
O5—N2	1.260 (2)	C5—H5	0.9300
O6—N2	1.218 (2)	C6—C7	1.403 (3)
O7—H7A	0.852 (9)	C6—H6	0.9300
O7—H7B	0.841 (9)	C7—C8	1.360 (3)
N1—C1	1.317 (2)	C7—H7	0.9300
N1—C9	1.368 (2)	C8—C9	1.411 (3)
N1—H1	0.8600	C10—C11	1.498 (3)
C1—C2	1.377 (3)	C10—H10A	0.9700
C1—H1A	0.9300	C10—H10B	0.9700
C2—C3	1.359 (3)
C8—O1—C10	117.04 (15)	C4—C5—H5	120.0
C11—O3—H3	109.5	C5—C6—C7	121.5 (2)
H7A—O7—H7B	114.9 (13)	C5—C6—H6	119.2
C1—N1—C9	122.98 (19)	C7—C6—H6	119.2
C1—N1—H1	118.5	C8—C7—C6	120.3 (2)
C9—N1—H1	118.5	C8—C7—H7	119.9
O6—N2—O4	121.1 (2)	C6—C7—H7	119.9
O6—N2—O5	119.9 (2)	C7—C8—O1	126.71 (18)
O4—N2—O5	119.1 (2)	C7—C8—C9	118.90 (19)
N1—C1—C2	120.3 (2)	O1—C8—C9	114.39 (17)
N1—C1—H1A	119.9	N1—C9—C4	118.56 (18)
C2—C1—H1A	119.9	N1—C9—C8	120.38 (18)
C3—C2—C1	119.6 (2)	C4—C9—C8	121.06 (19)
C3—C2—H2	120.2	O1—C10—C11	108.78 (16)
C1—C2—H2	120.2	O1—C10—H10A	109.9
C2—C3—C4	120.7 (2)	C11—C10—H10A	109.9
C2—C3—H3A	119.6	O1—C10—H10B	109.9
C4—C3—H3A	119.6	C11—C10—H10B	109.9
C9—C4—C3	117.8 (2)	H10A—C10—H10B	108.3
C9—C4—C5	118.3 (2)	O2—C11—O3	124.4 (2)
C3—C4—C5	123.9 (2)	O2—C11—C10	125.03 (19)
C6—C5—C4	120.0 (2)	O3—C11—C10	110.57 (19)
C6—C5—H5	120.0
C9—N1—C1—C2	0.8 (3)	C1—N1—C9—C4	0.8 (3)
N1—C1—C2—C3	−1.4 (4)	C1—N1—C9—C8	−178.5 (2)
C1—C2—C3—C4	0.4 (4)	C3—C4—C9—N1	−1.7 (3)
C2—C3—C4—C9	1.1 (3)	C5—C4—C9—N1	178.85 (19)
C2—C3—C4—C5	−179.4 (2)	C3—C4—C9—C8	177.63 (19)
C9—C4—C5—C6	1.5 (3)	C5—C4—C9—C8	−1.8 (3)
C3—C4—C5—C6	−177.9 (2)	C7—C8—C9—N1	179.70 (19)
C4—C5—C6—C7	0.3 (4)	O1—C8—C9—N1	−0.3 (3)
C5—C6—C7—C8	−1.8 (3)	C7—C8—C9—C4	0.4 (3)
C6—C7—C8—O1	−178.6 (2)	O1—C8—C9—C4	−179.64 (18)
C6—C7—C8—C9	1.4 (3)	C8—O1—C10—C11	−178.52 (17)
C10—O1—C8—C7	−3.3 (3)	O1—C10—C11—O2	3.0 (3)
C10—O1—C8—C9	176.72 (17)	O1—C10—C11—O3	−177.08 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O7	0.86	1.81	2.652 (2)	166
O7—H7B···O5i	0.841 (9)	2.610 (18)	3.140 (2)	122.3 (19)
O7—H7B···O2ii	0.841 (9)	2.085 (16)	2.852 (2)	152 (2)
O7—H7A···O1	0.852 (9)	2.52 (2)	2.943 (2)	111.6 (18)
O7—H7A···O2	0.852 (9)	1.929 (11)	2.776 (2)	172 (3)
O3—H3···O6iii	0.82	2.63	3.192 (2)	127
O3—H3···N2iii	0.82	2.55	3.301 (3)	154
O3—H3···O5iii	0.82	1.77	2.587 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O7	0.86	1.81	2.652 (2)	166
O7—H7B⋯O5i	0.841 (9)	2.610 (18)	3.140 (2)	122.3 (19)
O7—H7B⋯O2ii	0.841 (9)	2.085 (16)	2.852 (2)	152 (2)
O7—H7A⋯O1	0.852 (9)	2.52 (2)	2.943 (2)	111.6 (18)
O7—H7A⋯O2	0.852 (9)	1.929 (11)	2.776 (2)	172 (3)
O3—H3⋯O6iii	0.82	2.63	3.192 (2)	127
O3—H3⋯N2iii	0.82	2.55	3.301 (3)	154
O3—H3⋯O5iii	0.82	1.77	2.587 (2)	175

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