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[[[aqua­[2-(6-chloro­pyridin-3-yl)acetato-κO]sodium]-di-μ-aqua] monohydrate]

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: sundezhi@lcu.edu.cn

(Received 22 March 2012; accepted 31 March 2012; online 13 April 2012)

The crystal structure of the title compound, {[Na(C7H5ClNO2)(H2O)3]·H2O}n, features polymeric chains along [010]. The Na+ cation is octa­hedrally coordinated by four bridging water mol­ecules, a terminal water mol­ecule and an O atom derived from a monodentate carboxyl­ate ligand. Adjacent polyhedra share two O⋯O edges. The polymeric chains are linked into a three-dimensional network via O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For a related structure, see: Guo et al. (2004[Guo, M.-L. (2004). Acta Cryst. E60, m1684-m1685.]).

[Scheme 1]

Experimental

Crystal data
  • [Na(C7H5ClNO2)(H2O)3]·H2O

  • Mr = 265.62

  • Monoclinic, P 21 /c

  • a = 12.4695 (12) Å

  • b = 5.5377 (5) Å

  • c = 17.0557 (17) Å

  • β = 91.190 (1)°

  • V = 1177.48 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 298 K

  • 0.47 × 0.21 × 0.10 mm

Data collection
  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.844, Tmax = 0.964

  • 5621 measured reflections

  • 2082 independent reflections

  • 1558 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.084

  • S = 1.05

  • 2082 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Selected bond lengths (Å)

Na1—O1 2.3632 (15)
Na1—O5i 2.3872 (16)
Na1—O3ii 2.4032 (16)
Na1—O4 2.4239 (17)
Na1—O3 2.5142 (17)
Na1—O5 2.5187 (16)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3A⋯O4iii 0.85 2.06 2.893 (2) 168
O4—H4A⋯O2iv 0.85 1.91 2.762 (2) 175
O3—H3B⋯O6v 0.85 1.97 2.775 (2) 159
O4—H4B⋯O2v 0.85 1.98 2.824 (2) 169
O5—H5A⋯O6v 0.85 2.08 2.886 (2) 157
O5—H5B⋯O1ii 0.85 2.07 2.9214 (19) 175
O6—H6A⋯N1vi 0.85 2.05 2.900 (2) 173
O6—H6B⋯O2 0.85 1.95 2.796 (2) 176
Symmetry codes: (ii) -x+1, -y+2, -z+1; (iii) x, y+1, z; (iv) x, y-1, z; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In the title compound (Fig. 1), (I), the Na atom has a distorted O6 octahedral environment formed by a terminal water molecule O4, four O atoms derived from µ2-bridging water molecules and one carboxylate (O1) atom of the 6-chloro-3-pyridineacetate ligand (Table 1). Each coordination octahedron shares two O···O edges with two adjacent octahedra, thus producing infinite chains. Similar chains were found in the structure of sodium carboxynitrobenzoate tetrahydrate (Guo, 2004). In (I), the chains are linked into a three-dimensional network via O—H···O and O—H···N hydrogen bonds (Table 2 and Fig. 2).

Related literature top

For a related structure, see: Guo et al. (2004).

Experimental top

To a solution of 6-chloro-3-pyridineacetic acid (1 mmol) in doubly-distilled water (60 ml ), a solution of an equimolar amount of sodium hydroxide in doubly-distilled water (40 ml) was added drop wise at room temperature. After vigorous stirring for 4 h, the resulting mixture was evaporated in vacuo to a volume of about 20 ml and filtered hot. The filtrate was then set aside for crystallization at room temperature. Two weeks later, colourless crystals of the title compound were isolated.

Refinement top

The H atoms were placed in geometrically idealized positions (O—H = 0.85, C—H = 0.93–0.97 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.5Ueq(O) or Uiso(H) = 1.2Ueq(C).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The coordination environment around the Na atom showing numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: i - x + 1, -y + 1, -z + 1; ii - x + 1, -y + 2, -z + 1. The lattice water molecule and hydrogen atoms have been omitted.
[Figure 2] Fig. 2. Packing diagram of (I), showing hydrogen bonds as dashed lines.
catena-Poly[[[aqua[2-(6-chloropyridin-3-yl)acetato-κO]sodium]- di-µ-aqua] monohydrate] top
Crystal data top
[Na(C7H5ClNO2)(H2O)3]·H2OF(000) = 552
Mr = 265.62Dx = 1.498 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5621 reflections
a = 12.4695 (12) Åθ = 2.4–27.1°
b = 5.5377 (5) ŵ = 0.37 mm1
c = 17.0557 (17) ÅT = 298 K
β = 91.190 (1)°Block, colourless
V = 1177.48 (19) Å30.47 × 0.21 × 0.10 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
2082 independent reflections
Radiation source: fine-focus sealed tube1558 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 914
Tmin = 0.844, Tmax = 0.964k = 66
5621 measured reflectionsl = 1920
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0308P)2 + 0.4882P]
where P = (Fo2 + 2Fc2)/3
2082 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
[Na(C7H5ClNO2)(H2O)3]·H2OV = 1177.48 (19) Å3
Mr = 265.62Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4695 (12) ŵ = 0.37 mm1
b = 5.5377 (5) ÅT = 298 K
c = 17.0557 (17) Å0.47 × 0.21 × 0.10 mm
β = 91.190 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
2082 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1558 reflections with I > 2σ(I)
Tmin = 0.844, Tmax = 0.964Rint = 0.027
5621 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å3
2082 reflectionsΔρmin = 0.21 e Å3
145 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
O60.73121 (12)1.2862 (3)0.13436 (9)0.0499 (4)
Na10.55064 (6)0.74749 (14)0.44657 (5)0.0350 (2)
Cl11.11649 (5)0.25311 (12)0.44137 (4)0.0589 (2)
N11.04684 (13)0.6295 (3)0.36393 (11)0.0399 (5)
O10.69179 (11)0.9744 (3)0.39281 (8)0.0363 (4)
O20.64644 (11)1.1400 (3)0.27723 (8)0.0395 (4)
O30.42626 (11)1.0983 (3)0.42246 (8)0.0412 (4)
H3A0.44191.21940.39430.049*
H3B0.36941.03680.40270.049*
O40.51265 (12)0.4951 (3)0.33326 (9)0.0453 (4)
H4A0.55590.39220.31470.054*
H4B0.47140.54310.29610.054*
O50.37654 (11)0.6269 (2)0.50779 (8)0.0381 (4)
H5A0.33540.63600.46750.046*
H5B0.35900.73880.53910.046*
H6A0.79781.25320.13390.046*
H6B0.70821.24130.17860.046*
C10.70075 (15)0.9966 (4)0.32056 (12)0.0311 (5)
C20.78312 (18)0.8466 (4)0.27717 (13)0.0461 (6)
H2A0.74430.73620.24280.055*
H2B0.82300.95520.24400.055*
C30.97016 (17)0.7608 (4)0.32733 (13)0.0398 (5)
H30.99090.90160.30210.048*
C40.86306 (16)0.7010 (4)0.32460 (12)0.0337 (5)
C50.83412 (18)0.4939 (4)0.36460 (13)0.0395 (5)
H50.76230.44900.36620.047*
C60.91043 (18)0.3544 (4)0.40187 (13)0.0428 (6)
H60.89190.21430.42840.051*
C71.01530 (17)0.4294 (4)0.39851 (12)0.0368 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0327 (9)0.0665 (11)0.0504 (10)0.0073 (8)0.0012 (7)0.0212 (8)
Na10.0387 (5)0.0315 (4)0.0349 (5)0.0025 (4)0.0060 (4)0.0001 (4)
Cl10.0542 (4)0.0584 (4)0.0637 (4)0.0218 (3)0.0098 (3)0.0013 (3)
N10.0308 (10)0.0401 (11)0.0491 (11)0.0015 (9)0.0052 (9)0.0046 (9)
O10.0378 (8)0.0405 (8)0.0310 (8)0.0005 (7)0.0078 (6)0.0007 (7)
O20.0328 (8)0.0476 (9)0.0378 (9)0.0095 (7)0.0022 (7)0.0004 (8)
O30.0423 (9)0.0397 (9)0.0413 (9)0.0108 (7)0.0040 (7)0.0033 (7)
O40.0487 (9)0.0488 (9)0.0382 (9)0.0147 (8)0.0060 (7)0.0062 (7)
O50.0420 (9)0.0361 (8)0.0361 (8)0.0018 (7)0.0001 (7)0.0013 (7)
C10.0249 (10)0.0327 (11)0.0357 (12)0.0057 (9)0.0008 (9)0.0015 (10)
C20.0482 (14)0.0550 (14)0.0352 (12)0.0189 (12)0.0073 (10)0.0003 (11)
C30.0409 (13)0.0340 (11)0.0449 (13)0.0021 (10)0.0143 (10)0.0043 (11)
C40.0349 (12)0.0371 (12)0.0294 (11)0.0074 (9)0.0065 (9)0.0050 (9)
C50.0321 (12)0.0382 (12)0.0482 (14)0.0036 (10)0.0032 (10)0.0029 (11)
C60.0455 (14)0.0326 (12)0.0504 (14)0.0013 (11)0.0070 (11)0.0043 (11)
C70.0390 (13)0.0366 (12)0.0347 (12)0.0090 (10)0.0016 (10)0.0067 (10)
Geometric parameters (Å, º) top
O6—H6A0.8500O3—H3B0.8500
O6—H6B0.8502O4—H4A0.8500
Na1—O12.3632 (15)O4—H4B0.8500
Na1—O5i2.3872 (16)O5—Na1i2.3872 (16)
Na1—O3ii2.4032 (16)O5—H5A0.8499
Na1—O42.4239 (17)O5—H5B0.8500
Na1—O32.5142 (17)C1—C21.524 (3)
Na1—O52.5187 (16)C2—C41.505 (3)
Na1—Na1i3.5391 (15)C2—H2A0.9700
Na1—Na1ii3.5823 (15)C2—H2B0.9700
Cl1—C71.744 (2)C3—C41.376 (3)
N1—C71.319 (3)C3—H30.9300
N1—C31.344 (3)C4—C51.386 (3)
O1—C11.246 (2)C5—C61.371 (3)
O2—C11.271 (2)C5—H50.9300
O3—Na1ii2.4032 (16)C6—C71.374 (3)
O3—H3A0.8500C6—H60.9300
H6A—O6—H6B107.0Na1—O3—H3B105.2
O1—Na1—O5i107.88 (6)H3A—O3—H3B106.9
O1—Na1—O3ii95.50 (6)Na1—O4—H4A124.6
O5i—Na1—O3ii88.18 (5)Na1—O4—H4B121.3
O1—Na1—O497.59 (6)H4A—O4—H4B108.1
O5i—Na1—O479.97 (5)Na1i—O5—Na192.30 (5)
O3ii—Na1—O4164.52 (6)Na1i—O5—H5A122.3
O1—Na1—O389.29 (5)Na1—O5—H5A99.2
O5i—Na1—O3162.45 (6)Na1i—O5—H5B122.0
O3ii—Na1—O386.51 (6)Na1—O5—H5B107.6
O4—Na1—O3101.86 (6)H5A—O5—H5B107.8
O1—Na1—O5163.18 (6)O1—C1—O2125.41 (19)
O5i—Na1—O587.70 (5)O1—C1—C2120.11 (19)
O3ii—Na1—O578.27 (5)O2—C1—C2114.48 (18)
O4—Na1—O591.24 (6)C4—C2—C1118.45 (18)
O3—Na1—O574.85 (5)C4—C2—H2A107.7
O1—Na1—Na1i152.66 (6)C1—C2—H2A107.7
O5i—Na1—Na1i45.32 (4)C4—C2—H2B107.7
O3ii—Na1—Na1i80.43 (4)C1—C2—H2B107.7
O4—Na1—Na1i84.15 (5)H2A—C2—H2B107.1
O3—Na1—Na1i117.20 (5)N1—C3—C4124.5 (2)
O5—Na1—Na1i42.37 (4)N1—C3—H3117.8
O1—Na1—Na1ii93.18 (5)C4—C3—H3117.8
O5i—Na1—Na1ii130.38 (5)C3—C4—C5116.4 (2)
O3ii—Na1—Na1ii44.47 (4)C3—C4—C2121.4 (2)
O4—Na1—Na1ii142.25 (6)C5—C4—C2122.1 (2)
O3—Na1—Na1ii42.04 (4)C6—C5—C4120.6 (2)
O5—Na1—Na1ii71.35 (4)C6—C5—H5119.7
Na1i—Na1—Na1ii102.08 (4)C4—C5—H5119.7
C7—N1—C3116.48 (18)C5—C6—C7117.5 (2)
C1—O1—Na1121.26 (13)C5—C6—H6121.2
Na1ii—O3—Na193.49 (6)C7—C6—H6121.2
Na1ii—O3—H3A102.7N1—C7—C6124.4 (2)
Na1—O3—H3A123.6N1—C7—Cl1115.97 (16)
Na1ii—O3—H3B126.5C6—C7—Cl1119.60 (17)
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—H3A···O4iii0.852.062.893 (2)168
O4—H4A···O2iv0.851.912.762 (2)175
O3—H3B···O6v0.851.972.775 (2)159
O4—H4B···O2v0.851.982.824 (2)169
O5—H5A···O6v0.852.082.886 (2)157
O5—H5B···O1ii0.852.072.9214 (19)175
O6—H6A···N1vi0.852.052.900 (2)173
O6—H6B···O20.851.952.796 (2)176
Symmetry codes: (ii) x+1, y+2, z+1; (iii) x, y+1, z; (iv) x, y1, z; (v) x+1, y1/2, z+1/2; (vi) x+2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Na(C7H5ClNO2)(H2O)3]·H2O
Mr265.62
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.4695 (12), 5.5377 (5), 17.0557 (17)
β (°) 91.190 (1)
V3)1177.48 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.47 × 0.21 × 0.10
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.844, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
5621, 2082, 1558
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.084, 1.05
No. of reflections2082
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.21

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

Selected bond lengths (Å) top
Na1—O12.3632 (15)Na1—O42.4239 (17)
Na1—O5i2.3872 (16)Na1—O32.5142 (17)
Na1—O3ii2.4032 (16)Na1—O52.5187 (16)
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—H3A···O4iii0.852.062.893 (2)168
O4—H4A···O2iv0.851.912.762 (2)175
O3—H3B···O6v0.851.972.775 (2)159
O4—H4B···O2v0.851.982.824 (2)169
O5—H5A···O6v0.852.082.886 (2)157
O5—H5B···O1ii0.852.072.9214 (19)175
O6—H6A···N1vi0.852.052.900 (2)173
O6—H6B···O20.851.952.796 (2)176
Symmetry codes: (ii) x+1, y+2, z+1; (iii) x, y+1, z; (iv) x, y1, z; (v) x+1, y1/2, z+1/2; (vi) x+2, y+1/2, z+1/2.
 

Acknowledgements

The authors thank the State Key Laboratory of Crystal Materials (SRT11055HX2), Liaocheng University, China, and the Liaocheng University Foundation (xo9013) for financial support.

References

First citationGuo, M.-L. (2004). Acta Cryst. E60, m1684–m1685.  Web of Science CSD CrossRef IUCr Journals 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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