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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1641
doi:10.1107/S1600536808020357

8-(Carb­oxy­meth­oxy)­quinolinium nitrate monohydrate

Feng Sun,a Li Chen,a Hua-Cai Fang,a Xiao-Ming Lina and Yue-Peng Caia*

aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China
*Correspondence e-mail: ypcai8@yahoo.com

(Received 8 May 2008; accepted 2 July 2008; online 31 July 2008)

In the title compound, C11H10NO3+·NO3−·H2O, the planar 8-carboxy­methoxy­quinolinium cation, the nitrate anion and the water mol­ecule are dimerized by hydrogen bonds into square building-block units, and then further assembled into two-dimensional gently undulating supra­molecular layers.

Related literature

For general background, see Czugler & Kalman (1981[Czugler, M. & Kalman, A. (1981). J. Mol. Struct. 75, 29-37.]); Das et al. (1987[Das, V. G. K., Wei, C., Ng, S. W. & Mak, T. C. W. (1987). J. Organomet. Chem. 322, 33-47.]); Song et al. (2004[Song, R.-F., Wang, Y.-H. & Jiang, F. (2004). Acta Cryst. E60, m1695-m1696.]); Wang & Lu (2004[Wang, Y.-H. & Lu, F. (2004). Acta Cryst. C60, m557-m559.]).

[Scheme 1]

Experimental

Crystal data

  • C11H10NO3+·NO3−·H2O

  • Mr = 284.23

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.968, Tmax = 0.980

  • 6235 measured reflections

  • 2071 independent reflections

  • 1376 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 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

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) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y+2, -z+1; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020357/rn2043sup1.cif

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

checkCIF report


Comment top

There are no reports of the title compound but there are several reports on metal compounds involving the ligand 2-(quinolin-8-yloxy)acetate and its derivatives (Czugler & Kalman, 1981; Das et al., 1987; Wang & Lu, 2004; Song et al., 2004). The title compound (Scheme I) contains one cation, one nitrate anion and one water molecule (Fig.1).

Fig. 2 shows that the cation, the nitrate anion and water molecule are dimerized by the hydrogen bonds (Table 1) into stable square building block units, and then further assembled into 2D supramolecular layers which are gently undulating.

Related literature top

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

Experimental top

A solution of Cu(NO3)2 (363 mg, 1.00 mmol) in CH3OH (20 ml) was slowly added to a solution of 2-(quinolin-8-yloxy)acetic acid (410 mg, 1.95 mmol) in CH3OH (10 ml). The resultant blue solution was stirred for 2 h at room temperature and then filtered. Colorless crystals suitable for X-ray diffraction were obtained in two day by slow diffusion of diethyl ether into a dilute solution of the title complex in methanol. The assigned structure was substantiated by elemental analysis; calculated for C11H12N2O7: C 46.44, H 4.22, N 9.85%; found: C 46.36, H 4.28, N 9.82%.

Refinement top

The structure was solved using direct methods followed by Fourier synthesis. Non-H atoms were refined anisotropically. All of H atoms except water molecule were placed in idealized positions (C—H = 0.93 or 0.97 Å, O—H = 0.82 Å, N—H = 0.86 Å), forced to ride on the atom to which they are bonded, and were included in the refinement in the riding-model approximation. Uiso values were set equal to 1.5Ueq(parent atom) for methyl H atoms and to 1.2Ueq(parent atom)for all other H atoms. The water H atoms were located in a difference Fourier map, and were refined with distance restraints of O—H = 0.84 (1) and H···H 1.43 (2) Å, but their Uiso values were set equal to 1.5 Ueq(parent atom O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound (I). The atom-numbering scheme is shown and ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the dimerized supramolecular sheet constructed by hydrogen bonding interactions. Symmetry codes i: 1.5-x, 0.5+y, 0.5-z; ii: 2-x, 2-y, 1-z; iii: 0.5+x, 1.5-y, 0.5+z.
8-(Carboxymethoxy)quinolinium nitrate monohydrate top
Crystal data top
C11H10NO3+·NO3−·H2OF(000) = 592
Mr = 284.23Dx = 1.523 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 1544 reflections
a = 5.3577 (5) Åθ = 2.7–22.5°
b = 19.5100 (17) ŵ = 0.13 mm−1
c = 11.8959 (11) ÅT = 298 K
β = 94.663 (3)°Block, yellow
V = 1239.3 (2) Å30.25 × 0.22 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2071 independent reflections
Radiation source: fine-focus sealed tube1376 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −6→6
Tmin = 0.968, Tmax = 0.980k = −23→22
6235 measured reflectionsl = −14→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H 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 reflectionsΔρmax = 0.14 e Å−3
189 parametersΔρmin = −0.16 e Å−3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0044 (12)
Crystal data top
C11H10NO3+·NO3−·H2OV = 1239.3 (2) Å3
Mr = 284.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.3577 (5) ŵ = 0.13 mm−1
b = 19.5100 (17) ÅT = 298 K
c = 11.8959 (11) Å0.25 × 0.22 × 0.16 mm
β = 94.663 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2071 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1376 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.980Rint = 0.026
6235 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0403 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.14 e Å−3
2071 reflectionsΔρmin = −0.16 e Å−3
189 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3857 (3)1.04106 (6)0.31886 (12)0.0504 (4)
O20.7769 (3)1.08262 (7)0.45561 (14)0.0639 (5)
O30.6421 (3)1.19011 (7)0.44971 (15)0.0717 (5)
H30.77651.19750.48560.107*
O40.7649 (4)0.21455 (8)0.17156 (19)0.0945 (7)
O50.5562 (3)0.28962 (8)0.07269 (16)0.0761 (6)
O60.4361 (4)0.18475 (9)0.07206 (17)0.0943 (7)
O70.7613 (3)0.94258 (8)0.41435 (15)0.0697 (5)
H7A0.766 (4)0.9861 (5)0.420 (2)0.105*
H7B0.893 (3)0.9224 (10)0.439 (2)0.105*
N10.3815 (3)0.90790 (8)0.26857 (14)0.0478 (5)
H10.49420.92590.31500.057*
N20.5863 (4)0.22855 (10)0.10544 (17)0.0595 (5)
C10.3960 (5)0.84190 (10)0.24671 (19)0.0585 (6)
H1A0.52510.81590.28200.070*
C20.2210 (5)0.81128 (12)0.1718 (2)0.0678 (7)
H20.23350.76490.15520.081*
C30.0298 (5)0.84926 (12)0.1222 (2)0.0633 (7)
H3A−0.08900.82850.07190.076*
C40.0098 (4)0.91954 (11)0.14604 (17)0.0491 (6)
C5−0.1837 (5)0.96193 (13)0.09874 (19)0.0597 (6)
H5−0.31120.94340.05030.072*
C6−0.1842 (5)1.02966 (12)0.12375 (19)0.0592 (6)
H6−0.31341.05710.09230.071*
C70.0059 (4)1.05930 (11)0.19611 (18)0.0503 (6)
H70.00391.10620.21030.060*
C80.1930 (4)1.01977 (9)0.24550 (16)0.0428 (5)
C90.1954 (4)0.94906 (10)0.22072 (16)0.0415 (5)
C100.4012 (4)1.11253 (9)0.34252 (17)0.0480 (6)
H10A0.25181.12750.37640.058*
H10B0.41371.13800.27320.058*
C110.6279 (4)1.12555 (11)0.42193 (17)0.0482 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0499 (10)0.0361 (7)0.0612 (9)0.0015 (7)−0.0185 (8)−0.0028 (6)
O20.0534 (11)0.0450 (9)0.0881 (11)0.0037 (8)−0.0256 (9)−0.0097 (8)
O30.0775 (14)0.0385 (8)0.0930 (13)−0.0001 (8)−0.0295 (10)−0.0109 (8)
O40.0822 (14)0.0620 (11)0.1291 (16)0.0015 (10)−0.0530 (13)0.0185 (11)
O50.0753 (13)0.0433 (9)0.1048 (13)0.0006 (8)−0.0219 (10)0.0184 (9)
O60.0987 (16)0.0594 (10)0.1156 (15)−0.0244 (11)−0.0464 (13)0.0157 (10)
O70.0638 (12)0.0514 (9)0.0877 (12)0.0058 (8)−0.0320 (10)−0.0014 (9)
N10.0471 (12)0.0411 (10)0.0533 (10)−0.0052 (9)−0.0074 (9)0.0001 (8)
N20.0587 (14)0.0471 (12)0.0697 (13)0.0000 (11)−0.0124 (11)0.0048 (10)
C10.0633 (17)0.0381 (12)0.0723 (15)−0.0001 (11)−0.0047 (14)0.0011 (11)
C20.077 (2)0.0438 (13)0.0808 (17)−0.0116 (13)−0.0052 (15)−0.0090 (12)
C30.0669 (18)0.0577 (14)0.0630 (15)−0.0201 (13)−0.0083 (14)−0.0099 (12)
C40.0439 (14)0.0542 (13)0.0474 (12)−0.0082 (11)−0.0059 (11)−0.0006 (10)
C50.0461 (16)0.0749 (17)0.0552 (14)−0.0107 (13)−0.0143 (12)−0.0008 (12)
C60.0450 (15)0.0719 (16)0.0579 (14)0.0072 (13)−0.0120 (12)0.0073 (12)
C70.0455 (15)0.0474 (12)0.0562 (13)0.0041 (11)−0.0061 (12)0.0045 (10)
C80.0405 (14)0.0433 (12)0.0429 (11)−0.0027 (10)−0.0068 (11)0.0010 (9)
C90.0361 (13)0.0434 (11)0.0437 (11)−0.0018 (10)−0.0038 (10)0.0036 (9)
C100.0508 (15)0.0347 (11)0.0560 (13)0.0005 (10)−0.0102 (11)0.0011 (9)
C110.0506 (15)0.0400 (12)0.0528 (13)−0.0033 (11)−0.0038 (11)−0.0008 (10)
Geometric parameters (Å, º) top
O1—C81.362 (2)C2—H20.9300
O1—C101.424 (2)C3—C41.406 (3)
O2—C111.203 (2)C3—H3A0.9300
O3—C111.303 (2)C4—C91.402 (3)
O3—H30.8200C4—C51.407 (3)
O4—N21.219 (2)C5—C61.355 (3)
O5—N21.260 (2)C5—H50.9300
O6—N21.218 (2)C6—C71.403 (3)
O7—H7A0.852 (9)C6—H60.9300
O7—H7B0.841 (9)C7—C81.360 (3)
N1—C11.317 (2)C7—H70.9300
N1—C91.368 (2)C8—C91.411 (3)
N1—H10.8600C10—C111.498 (3)
C1—C21.377 (3)C10—H10A0.9700
C1—H1A0.9300C10—H10B0.9700
C2—C31.359 (3)
C8—O1—C10117.04 (15)C4—C5—H5120.0
C11—O3—H3109.5C5—C6—C7121.5 (2)
H7A—O7—H7B114.9 (13)C5—C6—H6119.2
C1—N1—C9122.98 (19)C7—C6—H6119.2
C1—N1—H1118.5C8—C7—C6120.3 (2)
C9—N1—H1118.5C8—C7—H7119.9
O6—N2—O4121.1 (2)C6—C7—H7119.9
O6—N2—O5119.9 (2)C7—C8—O1126.71 (18)
O4—N2—O5119.1 (2)C7—C8—C9118.90 (19)
N1—C1—C2120.3 (2)O1—C8—C9114.39 (17)
N1—C1—H1A119.9N1—C9—C4118.56 (18)
C2—C1—H1A119.9N1—C9—C8120.38 (18)
C3—C2—C1119.6 (2)C4—C9—C8121.06 (19)
C3—C2—H2120.2O1—C10—C11108.78 (16)
C1—C2—H2120.2O1—C10—H10A109.9
C2—C3—C4120.7 (2)C11—C10—H10A109.9
C2—C3—H3A119.6O1—C10—H10B109.9
C4—C3—H3A119.6C11—C10—H10B109.9
C9—C4—C3117.8 (2)H10A—C10—H10B108.3
C9—C4—C5118.3 (2)O2—C11—O3124.4 (2)
C3—C4—C5123.9 (2)O2—C11—C10125.03 (19)
C6—C5—C4120.0 (2)O3—C11—C10110.57 (19)
C6—C5—H5120.0
C9—N1—C1—C20.8 (3)C1—N1—C9—C40.8 (3)
N1—C1—C2—C3−1.4 (4)C1—N1—C9—C8−178.5 (2)
C1—C2—C3—C40.4 (4)C3—C4—C9—N1−1.7 (3)
C2—C3—C4—C91.1 (3)C5—C4—C9—N1178.85 (19)
C2—C3—C4—C5−179.4 (2)C3—C4—C9—C8177.63 (19)
C9—C4—C5—C61.5 (3)C5—C4—C9—C8−1.8 (3)
C3—C4—C5—C6−177.9 (2)C7—C8—C9—N1179.70 (19)
C4—C5—C6—C70.3 (4)O1—C8—C9—N1−0.3 (3)
C5—C6—C7—C8−1.8 (3)C7—C8—C9—C40.4 (3)
C6—C7—C8—O1−178.6 (2)O1—C8—C9—C4−179.64 (18)
C6—C7—C8—C91.4 (3)C8—O1—C10—C11−178.52 (17)
C10—O1—C8—C7−3.3 (3)O1—C10—C11—O23.0 (3)
C10—O1—C8—C9176.72 (17)O1—C10—C11—O3−177.08 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O70.861.812.652 (2)166
O7—H7B···O5i0.84 (1)2.61 (2)3.140 (2)122 (2)
O7—H7B···O2ii0.84 (1)2.09 (2)2.852 (2)152 (2)
O7—H7A···O10.85 (1)2.52 (2)2.943 (2)112 (2)
O7—H7A···O20.85 (1)1.93 (1)2.776 (2)172 (3)
O3—H3···O6iii0.822.633.192 (2)127
O3—H3···N2iii0.822.553.301 (3)154
O3—H3···O5iii0.821.772.587 (2)175
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z+1; (iii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H10NO3+·NO3−·H2O
Mr284.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)5.3577 (5), 19.5100 (17), 11.8959 (11)
β (°) 94.663 (3)
V (Å3)1239.3 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.25 × 0.22 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.968, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		6235, 2071, 1376
Rint0.026
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.107, 1.02
No. of reflections2071
No. of parameters189
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.14, −0.16

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O70.861.812.652 (2)165.9
O7—H7B···O5i0.841 (9)2.610 (18)3.140 (2)122.3 (19)
O7—H7B···O2ii0.841 (9)2.085 (16)2.852 (2)152 (2)
O7—H7A···O10.852 (9)2.52 (2)2.943 (2)111.6 (18)
O7—H7A···O20.852 (9)1.929 (11)2.776 (2)172 (3)
O3—H3···O6iii0.822.633.192 (2)127.0
O3—H3···N2iii0.822.553.301 (3)153.7
O3—H3···O5iii0.821.772.587 (2)175.4
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z+1; (iii) x+1/2, −y+3/2, z+1/2.
 

Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant No. 20772037)and the NSF of Guangdong Province, China (grant No. 06025033).

References

First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1641
doi:10.1107/S1600536808020357
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