PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m113.
Published online 2010 January 9. doi:  10.1107/S1600536809053999
PMCID: PMC2979834

catena-Poly[[[diaqua­sodium]-di-μ-aqua] 2-(2-pyrid­yl)quinoline-4-carboxyl­ate]

Abstract

In the title compound, [Na(H2O)4](C15H9N2O2), the Na+ ion is coordinated by six water mol­ecules in an octa­hedral geometry. The NaO6 octa­hedra are connected by sharing edges, forming a cationic chain along the b-axis direction. O—H(...)O and O—H(...)N hydrogen bonds link the chains and the 2-(2-pyrid­yl)quinoline-4-carboxyl­ate anions into a two-dimensional network parallel to (100).

Related literature

For the syntheses of sodium 2-(2-pyrid­yl)quinoline-4-carboxyl­ate and 2-(2-pyrid­yl)quinoline-4-carboxylic acid, see: Bass et al. (1997 [triangle]); Convers et al. (2004 [triangle]). For the structures of 2-(2-pyrid­yl)-4-methyl­carboxy­quinoline and its Ru complex, see: Farah et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m113-scheme1.jpg

Experimental

Crystal data

  • [Na(H2O)4](C15H9N2O2)
  • M r = 344.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m113-efi1.jpg
  • a = 19.0409 (17) Å
  • b = 5.2987 (5) Å
  • c = 16.8305 (16) Å
  • β = 103.107 (5)°
  • V = 1653.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 296 K
  • 0.43 × 0.35 × 0.30 mm

Data collection

  • Siemens SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.944, T max = 0.962
  • 14472 measured reflections
  • 3647 independent reflections
  • 2902 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.103
  • S = 1.05
  • 3647 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053999/hy2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053999/hy2255Isup2.hkl

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

Acknowledgments

This work was supported by the Innovation Project (gxun-chx2009080) of Guangxi University for Nationalities.

supplementary crystallographic information

Comment

2-(2-pyridyl)quinoline-4-carboxylic acid is a 2,2'-bipyridyl-like ligand containing a carboxylate substituent, which represents a simple route to some important functionalities. The syntheses of sodium 2-(2-pyridyl)quinoline-4-carboxylate and 2-(2-pyridyl)quinoline-4-carboxylic acid have been reported (Bass et al., 1997; Convers et al., 2004). The structures of 2-(2-pyridyl)-4-methylcarboxyquinoline and its Ru complex have been reported by Farah et al. (2003). Here we present the structure of a sodium salt of 2-(2-pyridyl)quinoline-4-carboxylate in a tetrahydrate form.

The molecular structure of the title compound is shown in Fig. 1. The NaI ion is coordinated by six water molecules in an octahedral geometry. Each coordination octahedron is connected with two adjacent ones by sharing edges, forming a cationic [Na(H2O)4]n chain along the b direction (Fig. 2).

In the crystal structure, the cationic chains and the organic anions are linked through O–H···O and O–H···N hydrogen bonds into a layer structure (Table 1 and Fig. 3).

Experimental

Sodium 2-(2-pyridyl)quinoline-4-carboxylate was prepared by a literature method (Bass et al.,1997). Colourless crystals were obtained by slow evaporation of an aqueous solution of this compound at room temperature.

Refinement

H atoms bonded C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C). H atoms of water molecules were found from difference Fourier maps and refined as riding atoms, with O—H = 0.85 Å and with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 2 - y, 1 - z.]
Fig. 2.
The chain of NaO6 octahedra along the b axis. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 2 - y, 1 - z.]
Fig. 3.
Crystal packing of the title compound viewed along the b axis. Dashed lines indicate hydrongen bonds.

Crystal data

[Na(H2O)4](C15H9N2O2)F(000) = 720
Mr = 344.30Dx = 1.383 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1202 reflections
a = 19.0409 (17) Åθ = 2.2–27.2°
b = 5.2987 (5) ŵ = 0.13 mm1
c = 16.8305 (16) ÅT = 296 K
β = 103.107 (5)°Block, colourless
V = 1653.8 (3) Å30.43 × 0.35 × 0.30 mm
Z = 4

Data collection

Siemens SMART 1000 CCD diffractometer3647 independent reflections
Radiation source: fine-focus sealed tube2902 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 27.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −24→24
Tmin = 0.944, Tmax = 0.962k = −6→6
14472 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0509P)2 + 0.3055P] where P = (Fo2 + 2Fc2)/3
3647 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.19 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Na10.46104 (3)0.74129 (10)0.43759 (3)0.03736 (16)
O40.53878 (5)0.39638 (18)0.42708 (6)0.0400 (2)
H4A0.52710.27410.39400.060*
H4B0.57670.46220.41750.060*
N10.12262 (5)1.0815 (2)0.20495 (6)0.0327 (3)
N20.21437 (6)0.6022 (2)0.34054 (7)0.0374 (3)
O60.40941 (6)1.10971 (19)0.47560 (6)0.0480 (3)
H6A0.38351.13460.50990.072*
H6B0.39011.21700.43970.072*
O50.49772 (5)0.96277 (19)0.33032 (6)0.0414 (2)
H5A0.46201.00100.29500.062*
H5B0.53150.89530.31230.062*
O30.36524 (5)0.5014 (2)0.36062 (6)0.0427 (3)
H500.32150.54700.35410.064*
H510.37050.42820.31740.064*
C70.20528 (7)1.3150 (2)0.14024 (7)0.0304 (3)
O20.38821 (5)1.2386 (2)0.22633 (6)0.0442 (3)
C90.17739 (6)0.9467 (2)0.24487 (7)0.0301 (3)
O10.34259 (5)1.1583 (2)0.09542 (6)0.0528 (3)
C110.24896 (7)0.9854 (3)0.23664 (8)0.0326 (3)
H110.28650.89040.26750.039*
C120.26262 (6)1.1624 (3)0.18334 (7)0.0305 (3)
C130.15995 (7)0.7438 (2)0.29892 (7)0.0314 (3)
C140.33714 (7)1.1890 (3)0.16692 (8)0.0341 (3)
C150.13590 (7)1.2676 (2)0.15413 (8)0.0314 (3)
C160.07768 (7)1.4199 (3)0.11366 (9)0.0402 (3)
H160.03161.38880.12120.048*
C170.21427 (8)1.5153 (3)0.08769 (8)0.0389 (3)
H170.25961.54820.07820.047*
C180.19828 (8)0.4159 (3)0.38732 (9)0.0439 (3)
H180.23600.31860.41670.053*
C190.07401 (8)0.5048 (3)0.35213 (9)0.0415 (3)
H190.02680.47180.35540.050*
C200.15707 (8)1.6597 (3)0.05106 (9)0.0449 (4)
H200.16371.79190.01720.054*
C210.12967 (8)0.3599 (3)0.39460 (9)0.0426 (3)
H210.12120.22730.42740.051*
C220.08920 (7)0.7007 (3)0.30439 (8)0.0387 (3)
H220.05220.80310.27610.046*
C230.08833 (8)1.6110 (3)0.06398 (9)0.0446 (4)
H230.04961.71040.03830.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na10.0418 (3)0.0330 (3)0.0387 (3)0.0028 (2)0.0121 (2)0.0002 (2)
O40.0428 (6)0.0361 (6)0.0460 (6)−0.0033 (4)0.0199 (4)−0.0019 (4)
N10.0270 (5)0.0375 (7)0.0341 (6)0.0005 (5)0.0081 (4)−0.0017 (5)
N20.0330 (6)0.0410 (7)0.0399 (6)0.0035 (5)0.0116 (5)0.0036 (5)
O60.0596 (7)0.0408 (6)0.0493 (6)0.0129 (5)0.0244 (5)0.0061 (5)
O50.0392 (5)0.0473 (6)0.0385 (5)0.0090 (5)0.0105 (4)0.0020 (4)
O30.0328 (5)0.0516 (6)0.0431 (5)0.0054 (4)0.0073 (4)−0.0010 (5)
C70.0299 (6)0.0330 (7)0.0283 (6)−0.0004 (5)0.0065 (5)−0.0040 (5)
O20.0270 (5)0.0637 (7)0.0421 (5)−0.0008 (4)0.0082 (4)0.0001 (5)
C90.0277 (6)0.0346 (7)0.0286 (6)0.0009 (5)0.0081 (5)−0.0035 (5)
O10.0405 (6)0.0841 (8)0.0389 (5)0.0043 (5)0.0197 (4)−0.0019 (5)
C110.0270 (6)0.0392 (8)0.0321 (6)0.0048 (5)0.0075 (5)0.0020 (5)
C120.0266 (6)0.0372 (7)0.0285 (6)−0.0002 (5)0.0078 (5)−0.0042 (5)
C130.0300 (6)0.0352 (7)0.0301 (6)0.0004 (5)0.0092 (5)−0.0036 (5)
C140.0297 (7)0.0376 (8)0.0373 (7)0.0033 (5)0.0126 (5)0.0033 (5)
C150.0281 (6)0.0340 (7)0.0313 (6)0.0001 (5)0.0054 (5)−0.0053 (5)
C160.0304 (7)0.0451 (9)0.0428 (8)0.0047 (6)0.0035 (6)0.0002 (6)
C170.0395 (7)0.0412 (8)0.0368 (7)−0.0029 (6)0.0101 (6)0.0007 (6)
C180.0430 (8)0.0426 (9)0.0472 (8)0.0074 (6)0.0126 (6)0.0087 (6)
C190.0361 (7)0.0478 (9)0.0432 (7)−0.0082 (6)0.0146 (6)−0.0019 (6)
C200.0521 (9)0.0400 (8)0.0407 (8)0.0014 (7)0.0068 (6)0.0063 (6)
C210.0513 (9)0.0369 (8)0.0430 (8)−0.0032 (7)0.0177 (6)0.0025 (6)
C220.0297 (7)0.0473 (9)0.0399 (7)0.0009 (6)0.0100 (5)0.0034 (6)
C230.0426 (8)0.0423 (9)0.0440 (8)0.0096 (6)−0.0008 (6)0.0023 (6)

Geometric parameters (Å, °)

Na1—O62.3393 (11)O2—C141.2544 (16)
Na1—O32.3559 (11)C9—C111.4157 (17)
Na1—O42.3834 (11)C9—C131.4935 (18)
Na1—O52.3867 (11)O1—C141.2419 (16)
Na1—O4i2.3909 (11)C11—C121.3632 (18)
Na1—O6ii2.6848 (13)C11—H110.9300
Na1—Na1i3.4262 (11)C12—C141.5124 (17)
Na1—Na1ii3.5661 (11)C13—C221.3897 (18)
O4—H4A0.85C15—C161.4148 (18)
O4—H4B0.85C16—C231.357 (2)
N1—C91.3159 (17)C16—H160.9300
N1—C151.3660 (17)C17—C201.359 (2)
N2—C181.3408 (18)C17—H170.9300
N2—C131.3409 (17)C18—C211.372 (2)
O6—H6A0.85C18—H180.9300
O6—H6B0.85C19—C211.371 (2)
O5—H5A0.82C19—C221.383 (2)
O5—H5B0.85C19—H190.9300
O3—H500.85C20—C231.399 (2)
O3—H510.85C20—H200.9300
C7—C151.4152 (17)C21—H210.9300
C7—C171.4167 (19)C22—H220.9300
C7—C121.4187 (18)C23—H230.9300
O6—Na1—O3106.24 (4)H50—O3—H51108.7
O6—Na1—O4165.19 (4)C15—C7—C17119.05 (12)
O3—Na1—O487.81 (4)C15—C7—C12116.97 (11)
O6—Na1—O590.56 (4)C17—C7—C12123.93 (12)
O3—Na1—O599.92 (4)N1—C9—C11122.72 (12)
O4—Na1—O591.59 (4)N1—C9—C13116.22 (11)
O6—Na1—O4i84.49 (4)C11—C9—C13121.04 (11)
O3—Na1—O4i101.12 (4)C12—C11—C9119.71 (12)
O4—Na1—O4i88.28 (4)C12—C11—H11120.1
O5—Na1—O4i158.94 (4)C9—C11—H11120.1
O6—Na1—O6ii89.83 (4)C11—C12—C7119.27 (11)
O3—Na1—O6ii163.58 (4)C11—C12—C14120.75 (12)
O4—Na1—O6ii75.91 (4)C7—C12—C14119.91 (11)
O5—Na1—O6ii82.92 (4)N2—C13—C22121.29 (12)
O4i—Na1—O6ii76.62 (4)N2—C13—C9117.95 (11)
O6—Na1—Na1i127.27 (4)C22—C13—C9120.76 (12)
O3—Na1—Na1i96.20 (3)O1—C14—O2125.45 (12)
O4—Na1—Na1i44.23 (3)O1—C14—C12116.92 (12)
O5—Na1—Na1i132.11 (4)O2—C14—C12117.63 (11)
O4i—Na1—Na1i44.05 (3)N1—C15—C16118.50 (11)
O6ii—Na1—Na1i70.68 (3)N1—C15—C7122.94 (12)
O6—Na1—Na1ii48.84 (3)C16—C15—C7118.57 (12)
O3—Na1—Na1ii154.91 (4)C23—C16—C15120.79 (13)
O4—Na1—Na1ii116.80 (3)C23—C16—H16119.6
O5—Na1—Na1ii85.04 (3)C15—C16—H16119.6
O4i—Na1—Na1ii76.28 (3)C20—C17—C7120.47 (13)
O6ii—Na1—Na1ii40.99 (2)C20—C17—H17119.8
Na1—O4—Na1i91.72 (4)C7—C17—H17119.8
Na1—O4—H4A123.9N2—C18—C21124.12 (14)
Na1i—O4—H4A109.5N2—C18—H18117.9
Na1—O4—H4B105.6C21—C18—H18117.9
Na1i—O4—H4B119.2C21—C19—C22118.97 (13)
H4A—O4—H4B107.2C21—C19—H19120.5
C9—N1—C15118.28 (11)C22—C19—H19120.5
C18—N2—C13117.78 (12)C17—C20—C23120.49 (14)
Na1—O6—Na1ii90.17 (4)C17—C20—H20119.8
Na1—O6—H6A131.3C23—C20—H20119.8
Na1ii—O6—H6A100.8C19—C21—C18118.11 (14)
Na1—O6—H6B120.3C19—C21—H21120.9
Na1ii—O6—H6B112.7C18—C21—H21120.9
H6A—O6—H6B98.9C19—C22—C13119.71 (13)
Na1—O5—H5A109.5C19—C22—H22120.1
Na1—O5—H5B116.0C13—C22—H22120.1
H5A—O5—H5B114.6C16—C23—C20120.62 (13)
Na1—O3—H50122.1C16—C23—H23119.7
Na1—O3—H51119.3C20—C23—H23119.7
O6—Na1—O4—Na1i60.71 (16)N1—C9—C13—C221.18 (18)
O3—Na1—O4—Na1i−101.20 (4)C11—C9—C13—C22−177.58 (12)
O5—Na1—O4—Na1i158.93 (4)C11—C12—C14—O1120.27 (15)
O4i—Na1—O4—Na1i0.0C7—C12—C14—O1−56.85 (18)
O6ii—Na1—O4—Na1i76.64 (4)C11—C12—C14—O2−59.32 (18)
Na1ii—Na1—O4—Na1i73.68 (4)C7—C12—C14—O2123.56 (14)
O3—Na1—O6—Na1ii176.58 (4)C9—N1—C15—C16−177.42 (12)
O4—Na1—O6—Na1ii15.43 (16)C9—N1—C15—C72.51 (18)
O5—Na1—O6—Na1ii−82.92 (4)C17—C7—C15—N1−178.81 (12)
O4i—Na1—O6—Na1ii76.58 (3)C12—C7—C15—N1−1.38 (18)
O6ii—Na1—O6—Na1ii0.0C17—C7—C15—C161.13 (18)
Na1i—Na1—O6—Na1ii65.29 (5)C12—C7—C15—C16178.56 (12)
C15—N1—C9—C11−0.61 (19)N1—C15—C16—C23178.51 (12)
C15—N1—C9—C13−179.35 (10)C7—C15—C16—C23−1.4 (2)
N1—C9—C11—C12−2.4 (2)C15—C7—C17—C20−0.1 (2)
C13—C9—C11—C12176.26 (12)C12—C7—C17—C20−177.32 (13)
C9—C11—C12—C73.49 (19)C13—N2—C18—C210.6 (2)
C9—C11—C12—C14−173.65 (12)C7—C17—C20—C23−0.7 (2)
C15—C7—C12—C11−1.68 (18)C22—C19—C21—C18−0.3 (2)
C17—C7—C12—C11175.61 (12)N2—C18—C21—C19−0.7 (2)
C15—C7—C12—C14175.49 (11)C21—C19—C22—C131.3 (2)
C17—C7—C12—C14−7.22 (19)N2—C13—C22—C19−1.5 (2)
C18—N2—C13—C220.5 (2)C9—C13—C22—C19177.24 (12)
C18—N2—C13—C9−178.27 (12)C15—C16—C23—C200.7 (2)
N1—C9—C13—N2179.93 (11)C17—C20—C23—C160.4 (2)
C11—C9—C13—N21.16 (18)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H50···N20.852.022.8657 (14)172
O3—H51···O2iii0.851.922.7722 (14)174
O4—H4A···O5iii0.851.982.8222 (14)172
O4—H4B···O1iv0.851.912.7494 (14)171
O5—H5A···O20.822.042.8093 (14)156
O5—H5B···O2iv0.851.972.8243 (13)178
O6—H6A···O1v0.852.102.8914 (14)156
O6—H6B···O3vi0.852.002.8321 (14)168

Symmetry codes: (iii) x, y−1, z; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+5/2, z+1/2; (vi) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2255).

References

  • Bass, Y., Morgan, R. J., Donovan, R. J. & Baker, A. D. (1997). Synth. Commun.27, 2165–2169.
  • Brandenburg, K. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Convers, E., Tye, H. & Whittaker, M. (2004). Tetrahedron, 60, 8729–8738.
  • Farah, A. A., Stynes, D. V. & Pietro, W. J. (2003). Inorg. Chim. Acta, 343, 295–306.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography