metal-organic compounds
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
The 7H5ClNO2)(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.
of the title compound, {[Na(CExperimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); 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.
Supporting information
10.1107/S1600536812014092/tk5075sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812014092/tk5075Isup2.hkl
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.
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).
Data collection: SMART (Siemens, 1996); cell
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).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. | |
Fig. 2. Packing diagram of (I), showing hydrogen bonds as dashed lines. |
[Na(C7H5ClNO2)(H2O)3]·H2O | F(000) = 552 |
Mr = 265.62 | Dx = 1.498 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5621 reflections |
a = 12.4695 (12) Å | θ = 2.4–27.1° |
b = 5.5377 (5) Å | µ = 0.37 mm−1 |
c = 17.0557 (17) Å | T = 298 K |
β = 91.190 (1)° | Block, colourless |
V = 1177.48 (19) Å3 | 0.47 × 0.21 × 0.10 mm |
Z = 4 |
Siemens SMART CCD area-detector diffractometer | 2082 independent reflections |
Radiation source: fine-focus sealed tube | 1558 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→14 |
Tmin = 0.844, Tmax = 0.964 | k = −6→6 |
5621 measured reflections | l = −19→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
[Na(C7H5ClNO2)(H2O)3]·H2O | V = 1177.48 (19) Å3 |
Mr = 265.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4695 (12) Å | µ = 0.37 mm−1 |
b = 5.5377 (5) Å | T = 298 K |
c = 17.0557 (17) Å | 0.47 × 0.21 × 0.10 mm |
β = 91.190 (1)° |
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 = 0.964 | Rint = 0.027 |
5621 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
2082 reflections | Δρmin = −0.21 e Å−3 |
145 parameters |
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 | ||
O6 | 0.73121 (12) | 1.2862 (3) | 0.13436 (9) | 0.0499 (4) | |
Na1 | 0.55064 (6) | 0.74749 (14) | 0.44657 (5) | 0.0350 (2) | |
Cl1 | 1.11649 (5) | 0.25311 (12) | 0.44137 (4) | 0.0589 (2) | |
N1 | 1.04684 (13) | 0.6295 (3) | 0.36393 (11) | 0.0399 (5) | |
O1 | 0.69179 (11) | 0.9744 (3) | 0.39281 (8) | 0.0363 (4) | |
O2 | 0.64644 (11) | 1.1400 (3) | 0.27723 (8) | 0.0395 (4) | |
O3 | 0.42626 (11) | 1.0983 (3) | 0.42246 (8) | 0.0412 (4) | |
H3A | 0.4419 | 1.2194 | 0.3943 | 0.049* | |
H3B | 0.3694 | 1.0368 | 0.4027 | 0.049* | |
O4 | 0.51265 (12) | 0.4951 (3) | 0.33326 (9) | 0.0453 (4) | |
H4A | 0.5559 | 0.3922 | 0.3147 | 0.054* | |
H4B | 0.4714 | 0.5431 | 0.2961 | 0.054* | |
O5 | 0.37654 (11) | 0.6269 (2) | 0.50779 (8) | 0.0381 (4) | |
H5A | 0.3354 | 0.6360 | 0.4675 | 0.046* | |
H5B | 0.3590 | 0.7388 | 0.5391 | 0.046* | |
H6A | 0.7978 | 1.2532 | 0.1339 | 0.046* | |
H6B | 0.7082 | 1.2413 | 0.1786 | 0.046* | |
C1 | 0.70075 (15) | 0.9966 (4) | 0.32056 (12) | 0.0311 (5) | |
C2 | 0.78312 (18) | 0.8466 (4) | 0.27717 (13) | 0.0461 (6) | |
H2A | 0.7443 | 0.7362 | 0.2428 | 0.055* | |
H2B | 0.8230 | 0.9552 | 0.2440 | 0.055* | |
C3 | 0.97016 (17) | 0.7608 (4) | 0.32733 (13) | 0.0398 (5) | |
H3 | 0.9909 | 0.9016 | 0.3021 | 0.048* | |
C4 | 0.86306 (16) | 0.7010 (4) | 0.32460 (12) | 0.0337 (5) | |
C5 | 0.83412 (18) | 0.4939 (4) | 0.36460 (13) | 0.0395 (5) | |
H5 | 0.7623 | 0.4490 | 0.3662 | 0.047* | |
C6 | 0.91043 (18) | 0.3544 (4) | 0.40187 (13) | 0.0428 (6) | |
H6 | 0.8919 | 0.2143 | 0.4284 | 0.051* | |
C7 | 1.01530 (17) | 0.4294 (4) | 0.39851 (12) | 0.0368 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O6 | 0.0327 (9) | 0.0665 (11) | 0.0504 (10) | 0.0073 (8) | 0.0012 (7) | 0.0212 (8) |
Na1 | 0.0387 (5) | 0.0315 (4) | 0.0349 (5) | −0.0025 (4) | 0.0060 (4) | 0.0001 (4) |
Cl1 | 0.0542 (4) | 0.0584 (4) | 0.0637 (4) | 0.0218 (3) | −0.0098 (3) | −0.0013 (3) |
N1 | 0.0308 (10) | 0.0401 (11) | 0.0491 (11) | 0.0015 (9) | 0.0052 (9) | −0.0046 (9) |
O1 | 0.0378 (8) | 0.0405 (8) | 0.0310 (8) | −0.0005 (7) | 0.0078 (6) | 0.0007 (7) |
O2 | 0.0328 (8) | 0.0476 (9) | 0.0378 (9) | 0.0095 (7) | −0.0022 (7) | −0.0004 (8) |
O3 | 0.0423 (9) | 0.0397 (9) | 0.0413 (9) | −0.0108 (7) | −0.0040 (7) | 0.0033 (7) |
O4 | 0.0487 (9) | 0.0488 (9) | 0.0382 (9) | 0.0147 (8) | −0.0060 (7) | −0.0062 (7) |
O5 | 0.0420 (9) | 0.0361 (8) | 0.0361 (8) | 0.0018 (7) | −0.0001 (7) | −0.0013 (7) |
C1 | 0.0249 (10) | 0.0327 (11) | 0.0357 (12) | −0.0057 (9) | 0.0008 (9) | −0.0015 (10) |
C2 | 0.0482 (14) | 0.0550 (14) | 0.0352 (12) | 0.0189 (12) | 0.0073 (10) | −0.0003 (11) |
C3 | 0.0409 (13) | 0.0340 (11) | 0.0449 (13) | 0.0021 (10) | 0.0143 (10) | 0.0043 (11) |
C4 | 0.0349 (12) | 0.0371 (12) | 0.0294 (11) | 0.0074 (9) | 0.0065 (9) | −0.0050 (9) |
C5 | 0.0321 (12) | 0.0382 (12) | 0.0482 (14) | −0.0036 (10) | 0.0032 (10) | −0.0029 (11) |
C6 | 0.0455 (14) | 0.0326 (12) | 0.0504 (14) | −0.0013 (11) | 0.0070 (11) | 0.0043 (11) |
C7 | 0.0390 (13) | 0.0366 (12) | 0.0347 (12) | 0.0090 (10) | 0.0016 (10) | −0.0067 (10) |
O6—H6A | 0.8500 | O3—H3B | 0.8500 |
O6—H6B | 0.8502 | O4—H4A | 0.8500 |
Na1—O1 | 2.3632 (15) | O4—H4B | 0.8500 |
Na1—O5i | 2.3872 (16) | O5—Na1i | 2.3872 (16) |
Na1—O3ii | 2.4032 (16) | O5—H5A | 0.8499 |
Na1—O4 | 2.4239 (17) | O5—H5B | 0.8500 |
Na1—O3 | 2.5142 (17) | C1—C2 | 1.524 (3) |
Na1—O5 | 2.5187 (16) | C2—C4 | 1.505 (3) |
Na1—Na1i | 3.5391 (15) | C2—H2A | 0.9700 |
Na1—Na1ii | 3.5823 (15) | C2—H2B | 0.9700 |
Cl1—C7 | 1.744 (2) | C3—C4 | 1.376 (3) |
N1—C7 | 1.319 (3) | C3—H3 | 0.9300 |
N1—C3 | 1.344 (3) | C4—C5 | 1.386 (3) |
O1—C1 | 1.246 (2) | C5—C6 | 1.371 (3) |
O2—C1 | 1.271 (2) | C5—H5 | 0.9300 |
O3—Na1ii | 2.4032 (16) | C6—C7 | 1.374 (3) |
O3—H3A | 0.8500 | C6—H6 | 0.9300 |
H6A—O6—H6B | 107.0 | Na1—O3—H3B | 105.2 |
O1—Na1—O5i | 107.88 (6) | H3A—O3—H3B | 106.9 |
O1—Na1—O3ii | 95.50 (6) | Na1—O4—H4A | 124.6 |
O5i—Na1—O3ii | 88.18 (5) | Na1—O4—H4B | 121.3 |
O1—Na1—O4 | 97.59 (6) | H4A—O4—H4B | 108.1 |
O5i—Na1—O4 | 79.97 (5) | Na1i—O5—Na1 | 92.30 (5) |
O3ii—Na1—O4 | 164.52 (6) | Na1i—O5—H5A | 122.3 |
O1—Na1—O3 | 89.29 (5) | Na1—O5—H5A | 99.2 |
O5i—Na1—O3 | 162.45 (6) | Na1i—O5—H5B | 122.0 |
O3ii—Na1—O3 | 86.51 (6) | Na1—O5—H5B | 107.6 |
O4—Na1—O3 | 101.86 (6) | H5A—O5—H5B | 107.8 |
O1—Na1—O5 | 163.18 (6) | O1—C1—O2 | 125.41 (19) |
O5i—Na1—O5 | 87.70 (5) | O1—C1—C2 | 120.11 (19) |
O3ii—Na1—O5 | 78.27 (5) | O2—C1—C2 | 114.48 (18) |
O4—Na1—O5 | 91.24 (6) | C4—C2—C1 | 118.45 (18) |
O3—Na1—O5 | 74.85 (5) | C4—C2—H2A | 107.7 |
O1—Na1—Na1i | 152.66 (6) | C1—C2—H2A | 107.7 |
O5i—Na1—Na1i | 45.32 (4) | C4—C2—H2B | 107.7 |
O3ii—Na1—Na1i | 80.43 (4) | C1—C2—H2B | 107.7 |
O4—Na1—Na1i | 84.15 (5) | H2A—C2—H2B | 107.1 |
O3—Na1—Na1i | 117.20 (5) | N1—C3—C4 | 124.5 (2) |
O5—Na1—Na1i | 42.37 (4) | N1—C3—H3 | 117.8 |
O1—Na1—Na1ii | 93.18 (5) | C4—C3—H3 | 117.8 |
O5i—Na1—Na1ii | 130.38 (5) | C3—C4—C5 | 116.4 (2) |
O3ii—Na1—Na1ii | 44.47 (4) | C3—C4—C2 | 121.4 (2) |
O4—Na1—Na1ii | 142.25 (6) | C5—C4—C2 | 122.1 (2) |
O3—Na1—Na1ii | 42.04 (4) | C6—C5—C4 | 120.6 (2) |
O5—Na1—Na1ii | 71.35 (4) | C6—C5—H5 | 119.7 |
Na1i—Na1—Na1ii | 102.08 (4) | C4—C5—H5 | 119.7 |
C7—N1—C3 | 116.48 (18) | C5—C6—C7 | 117.5 (2) |
C1—O1—Na1 | 121.26 (13) | C5—C6—H6 | 121.2 |
Na1ii—O3—Na1 | 93.49 (6) | C7—C6—H6 | 121.2 |
Na1ii—O3—H3A | 102.7 | N1—C7—C6 | 124.4 (2) |
Na1—O3—H3A | 123.6 | N1—C7—Cl1 | 115.97 (16) |
Na1ii—O3—H3B | 126.5 | C6—C7—Cl1 | 119.60 (17) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | 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−1/2, −z+1/2; (vi) −x+2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Na(C7H5ClNO2)(H2O)3]·H2O |
Mr | 265.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.4695 (12), 5.5377 (5), 17.0557 (17) |
β (°) | 91.190 (1) |
V (Å3) | 1177.48 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.47 × 0.21 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.844, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5621, 2082, 1558 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.084, 1.05 |
No. of reflections | 2082 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.21 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Na1—O1 | 2.3632 (15) | Na1—O4 | 2.4239 (17) |
Na1—O5i | 2.3872 (16) | Na1—O3 | 2.5142 (17) |
Na1—O3ii | 2.4032 (16) | Na1—O5 | 2.5187 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | 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−1/2, −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
Guo, M.-L. (2004). Acta Cryst. E60, m1684–m1685. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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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).