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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit    -P 2yab
PLAT774_ALERT_1_C Suspect X-Y Bond in CIF:   NA1    --  NA1     ..       3.54 Ang.
PLAT774_ALERT_1_C Suspect X-Y Bond in CIF:   NA1    --  NA1     ..       3.58 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          6
PLAT927_ALERT_1_C Reported and Calculated  wR2 Differ by .........    -0.0021

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          8
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.24 Ratio
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          50 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.5U_eq(O) or U_iso(H) = 1.2U_eq(C).

Computing details

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

	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.

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

Crystal data

[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) Å^3	0.47 × 0.21 × 0.10 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0308P)^2 + 0.4882P] where P = (Fo^2 + 2Fc^2)/3
2082 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—O5^i	2.3872 (16)	O5—Na1^i	2.3872 (16)
Na1—O3^ii	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—Na1^i	3.5391 (15)	C2—H2A	0.9700
Na1—Na1^ii	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—Na1^ii	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—O5^i	107.88 (6)	H3A—O3—H3B	106.9
O1—Na1—O3^ii	95.50 (6)	Na1—O4—H4A	124.6
O5^i—Na1—O3^ii	88.18 (5)	Na1—O4—H4B	121.3
O1—Na1—O4	97.59 (6)	H4A—O4—H4B	108.1
O5^i—Na1—O4	79.97 (5)	Na1^i—O5—Na1	92.30 (5)
O3^ii—Na1—O4	164.52 (6)	Na1^i—O5—H5A	122.3
O1—Na1—O3	89.29 (5)	Na1—O5—H5A	99.2
O5^i—Na1—O3	162.45 (6)	Na1^i—O5—H5B	122.0
O3^ii—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)
O5^i—Na1—O5	87.70 (5)	O1—C1—C2	120.11 (19)
O3^ii—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—Na1^i	152.66 (6)	C1—C2—H2A	107.7
O5^i—Na1—Na1^i	45.32 (4)	C4—C2—H2B	107.7
O3^ii—Na1—Na1^i	80.43 (4)	C1—C2—H2B	107.7
O4—Na1—Na1^i	84.15 (5)	H2A—C2—H2B	107.1
O3—Na1—Na1^i	117.20 (5)	N1—C3—C4	124.5 (2)
O5—Na1—Na1^i	42.37 (4)	N1—C3—H3	117.8
O1—Na1—Na1^ii	93.18 (5)	C4—C3—H3	117.8
O5^i—Na1—Na1^ii	130.38 (5)	C3—C4—C5	116.4 (2)
O3^ii—Na1—Na1^ii	44.47 (4)	C3—C4—C2	121.4 (2)
O4—Na1—Na1^ii	142.25 (6)	C5—C4—C2	122.1 (2)
O3—Na1—Na1^ii	42.04 (4)	C6—C5—C4	120.6 (2)
O5—Na1—Na1^ii	71.35 (4)	C6—C5—H5	119.7
Na1^i—Na1—Na1^ii	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
Na1^ii—O3—Na1	93.49 (6)	C7—C6—H6	121.2
Na1^ii—O3—H3A	102.7	N1—C7—C6	124.4 (2)
Na1—O3—H3A	123.6	N1—C7—Cl1	115.97 (16)
Na1^ii—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.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4^iii	0.85	2.06	2.893 (2)	168
O4—H4A···O2^iv	0.85	1.91	2.762 (2)	175
O3—H3B···O6^v	0.85	1.97	2.775 (2)	159
O4—H4B···O2^v	0.85	1.98	2.824 (2)	169
O5—H5A···O6^v	0.85	2.08	2.886 (2)	157
O5—H5B···O1^ii	0.85	2.07	2.9214 (19)	175
O6—H6A···N1^vi	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.