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

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ISSN: 2056-9890

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

aCollege of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China, and bSchool of Chemistry & Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China
*Correspondence e-mail: yxhphd@163.com

(Received 11 November 2009; accepted 15 December 2009; online 9 January 2010)

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[Bass, Y., Morgan, R. J., Donovan, R. J. & Baker, A. D. (1997). Synth. Commun. 27, 2165-2169.]); Convers et al. (2004[Convers, E., Tye, H. & Whittaker, M. (2004). Tetrahedron, 60, 8729-8738.]). For the structures of 2-(2-pyrid­yl)-4-methyl­carboxy­quinoline and its Ru complex, see: Farah et al. (2003[Farah, A. A., Stynes, D. V. & Pietro, W. J. (2003). Inorg. Chim. Acta, 343, 295-306.]).

[Scheme 1]

Experimental

Crystal data
  • [Na(H2O)4](C15H9N2O2)

  • Mr = 344.30

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.944, Tmax = 0.962

  • 14472 measured reflections

  • 3647 independent reflections

  • 2902 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H50⋯N2 0.85 2.02 2.8657 (14) 172
O3—H51⋯O2i 0.85 1.92 2.7722 (14) 174
O4—H4A⋯O5i 0.85 1.98 2.8222 (14) 172
O4—H4B⋯O1ii 0.85 1.91 2.7494 (14) 171
O5—H5A⋯O2 0.82 2.04 2.8093 (14) 156
O5—H5B⋯O2ii 0.85 1.97 2.8243 (13) 178
O6—H6A⋯O1iii 0.85 2.10 2.8914 (14) 156
O6—H6B⋯O3iv 0.85 2.00 2.8321 (14) 168
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]; (iv) x, y+1, z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Structure description top

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).

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

Computing details top

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

Figures top
[Figure 1] 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.]
[Figure 2] 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.]
[Figure 3] Fig. 3. Crystal packing of the title compound viewed along the b axis. Dashed lines indicate hydrongen bonds.
catena-Poly[[[diaquasodium]-di-µ-aqua] 2-(2-pyridyl)quinoline-4-carboxylate] top
Crystal data top
[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 top
Siemens SMART 1000 CCD
diffractometer
3647 independent reflections
Radiation source: fine-focus sealed tube2902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 27.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.944, Tmax = 0.962k = 66
14472 measured reflectionsl = 2121
Refinement top
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 = 1.05 w = 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
Crystal data top
[Na(H2O)4](C15H9N2O2)V = 1653.8 (3) Å3
Mr = 344.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.0409 (17) ŵ = 0.13 mm1
b = 5.2987 (5) ÅT = 296 K
c = 16.8305 (16) Å0.43 × 0.35 × 0.30 mm
β = 103.107 (5)°
Data collection top
Siemens SMART 1000 CCD
diffractometer
3647 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2902 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.962Rint = 0.028
14472 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.05Δρmax = 0.30 e Å3
3647 reflectionsΔρmin = 0.19 e Å3
218 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—Na1i101.20 (4)C11—C9—C13—C22177.58 (12)
O5—Na1—O4—Na1i158.93 (4)C11—C12—C14—O1120.27 (15)
O4i—Na1—O4—Na1i0.0C7—C12—C14—O156.85 (18)
O6ii—Na1—O4—Na1i76.64 (4)C11—C12—C14—O259.32 (18)
Na1ii—Na1—O4—Na1i73.68 (4)C7—C12—C14—O2123.56 (14)
O3—Na1—O6—Na1ii176.58 (4)C9—N1—C15—C16177.42 (12)
O4—Na1—O6—Na1ii15.43 (16)C9—N1—C15—C72.51 (18)
O5—Na1—O6—Na1ii82.92 (4)C17—C7—C15—N1178.81 (12)
O4i—Na1—O6—Na1ii76.58 (3)C12—C7—C15—N11.38 (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—C110.61 (19)N1—C15—C16—C23178.51 (12)
C15—N1—C9—C13179.35 (10)C7—C15—C16—C231.4 (2)
N1—C9—C11—C122.4 (2)C15—C7—C17—C200.1 (2)
C13—C9—C11—C12176.26 (12)C12—C7—C17—C20177.32 (13)
C9—C11—C12—C73.49 (19)C13—N2—C18—C210.6 (2)
C9—C11—C12—C14173.65 (12)C7—C17—C20—C230.7 (2)
C15—C7—C12—C111.68 (18)C22—C19—C21—C180.3 (2)
C17—C7—C12—C11175.61 (12)N2—C18—C21—C190.7 (2)
C15—C7—C12—C14175.49 (11)C21—C19—C22—C131.3 (2)
C17—C7—C12—C147.22 (19)N2—C13—C22—C191.5 (2)
C18—N2—C13—C220.5 (2)C9—C13—C22—C19177.24 (12)
C18—N2—C13—C9178.27 (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, º) top
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, y1, z; (iv) x+1, y1/2, z+1/2; (v) x, y+5/2, z+1/2; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Na(H2O)4](C15H9N2O2)
Mr344.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)19.0409 (17), 5.2987 (5), 16.8305 (16)
β (°) 103.107 (5)
V3)1653.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.43 × 0.35 × 0.30
Data collection
DiffractometerSiemens SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.944, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
14472, 3647, 2902
Rint0.028
(sin θ/λ)max1)0.643
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.103, 1.05
No. of reflections3647
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H50···N20.852.022.8657 (14)172
O3—H51···O2i0.851.922.7722 (14)174
O4—H4A···O5i0.851.982.8222 (14)172
O4—H4B···O1ii0.851.912.7494 (14)171
O5—H5A···O20.822.042.8093 (14)156
O5—H5B···O2ii0.851.972.8243 (13)178
O6—H6A···O1iii0.852.102.8914 (14)156
O6—H6B···O3iv0.852.002.8321 (14)168
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1/2; (iii) x, y+5/2, z+1/2; (iv) x, y+1, z.
 

Acknowledgements

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

References

First citationBass, Y., Morgan, R. J., Donovan, R. J. & Baker, A. D. (1997). Synth. Commun. 27, 2165–2169.  CrossRef CAS Web of Science Google Scholar
First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationConvers, E., Tye, H. & Whittaker, M. (2004). Tetrahedron, 60, 8729–8738.  Web of Science CrossRef CAS Google Scholar
First citationFarah, A. A., Stynes, D. V. & Pietro, W. J. (2003). Inorg. Chim. Acta, 343, 295–306.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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