Sodium 2-nitro-cinnamate dihydrate: a one-dimensional hydrogen-bonded coordination polymer.

The title compound catena-poly[aqua-sodium-μ(2)-aqua-μ(3)-2-nitro-cinnamato], [Na(C(9)H(6)NO(4))(H(2)O)(2)](n), the sodium salt of trans-2-nitro-cinnamic acid, is a one-dimensional coordination polymer based on six-coordinate octa-hedral NaO(6) centres, comprising three facially related monodentate carboxyl-ate O-atom donors from separate ligands (all bridging) [Na-O = 2.4370 (13)-2.5046 (13) Å], and three water mol-ecules (two bridging and one monodentate) [Na-O = 2.3782 (13)-2.4404 (17) Å]. The structure is also stabilized by intra-chain water-carboxyl-ate and water-nitro O-H⋯O hydrogen bonds.

Related literature

For literature on similar compounds, see: Crowther et al. (2008 ▶); Kariuki et al. (1995 ▶); Kula et al. (2007 ▶); Schmidt (1964 ▶); Smith et al. (2006 ▶); Trividi et al. (2005 ▶).

Experimental

Crystal data

[Na(C9H6NO4)(H2O)2]

M = 251.17

Monoclinic,

a = 19.4179 (7) Å

b = 3.6899 (2) Å

c = 14.8738 (7) Å

β = 92.239 (4)°

V = 1064.90 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 297 K

0.40 × 0.30 × 0.13 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.93, T max = 0.98

6531 measured reflections

2100 independent reflections

1626 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.09

2100 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030402/su2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030402/su2131Isup2.hkl

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

[Na(C9H6NO4)(H2O)2]	F(000) = 520
Mr = 251.17	Dx = 1.567 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2943 reflections
a = 19.4179 (7) Å	θ = 3.0–28.7°
b = 3.6899 (2) Å	µ = 0.17 mm−1
c = 14.8738 (7) Å	T = 297 K
β = 92.239 (4)°	Plate, colourless
V = 1064.90 (9) Å3	0.40 × 0.30 × 0.13 mm
Z = 4

Oxford Diffraction Gemini-S CCD-detector diffractometer	2100 independent reflections
Radiation source: Enhance (Mo) X-ray source	1626 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→21
Tmin = 0.93, Tmax = 0.98	k = −4→4
6531 measured reflections	l = −18→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0708P)2] where P = (Fo2 + 2Fc2)/3
2100 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Na1	0.05494 (3)	0.73072 (17)	−0.06704 (4)	0.0272 (2)
O1W	0.02635 (6)	0.2374 (3)	−0.16440 (8)	0.0319 (4)
O2W	0.16105 (8)	0.6812 (5)	−0.14886 (12)	0.0691 (7)
O21	0.29871 (7)	0.4625 (6)	0.31366 (9)	0.0637 (6)
O22	0.39979 (7)	0.2280 (5)	0.32066 (10)	0.0541 (6)
O31	0.06940 (6)	0.2430 (3)	0.04255 (8)	0.0282 (4)
O32	0.10417 (6)	0.0743 (4)	0.18086 (8)	0.0336 (4)
N21	0.35246 (7)	0.3769 (4)	0.27927 (10)	0.0339 (5)
C1	0.30837 (8)	0.4562 (5)	0.12070 (11)	0.0267 (5)
C2	0.36252 (8)	0.4742 (4)	0.18535 (11)	0.0261 (5)
C3	0.42813 (9)	0.5880 (5)	0.16617 (12)	0.0327 (6)
C4	0.44154 (10)	0.6987 (5)	0.08063 (14)	0.0384 (6)
C5	0.38972 (10)	0.6860 (5)	0.01494 (13)	0.0368 (6)
C6	0.32514 (9)	0.5634 (5)	0.03431 (12)	0.0346 (6)
C11	0.23935 (9)	0.3141 (5)	0.13955 (12)	0.0297 (5)
C21	0.18383 (9)	0.3638 (5)	0.08772 (13)	0.0345 (6)
C31	0.11421 (8)	0.2155 (4)	0.10637 (11)	0.0256 (5)
H3	0.46290	0.58950	0.21090	0.0390*
H4	0.48520	0.78150	0.06720	0.0460*
H5	0.39850	0.76120	−0.04320	0.0440*
H6	0.29140	0.55150	−0.01180	0.0420*
H11	0.23490	0.17970	0.19190	0.0360*
H11W	0.0460 (11)	0.241 (6)	−0.209 (2)	0.055 (8)*
H12W	−0.0168 (12)	0.157 (7)	−0.1733 (17)	0.044 (8)*
H21	0.18810	0.50100	0.03580	0.0410*
H21W	0.1828 (16)	0.851 (9)	−0.138 (2)	0.093 (13)*
H22W	0.1500 (18)	0.666 (12)	−0.209 (2)	0.101 (14)*

	U11	U22	U33	U12	U13	U23
Na1	0.0279 (4)	0.0275 (4)	0.0260 (4)	−0.0019 (3)	−0.0005 (3)	0.0007 (3)
O1W	0.0363 (7)	0.0350 (7)	0.0244 (7)	−0.0082 (5)	0.0026 (5)	−0.0002 (5)
O2W	0.0399 (9)	0.1143 (15)	0.0532 (10)	−0.0214 (9)	0.0046 (7)	0.0098 (9)
O21	0.0357 (8)	0.1222 (15)	0.0337 (8)	0.0081 (9)	0.0067 (6)	−0.0065 (9)
O22	0.0475 (9)	0.0775 (12)	0.0364 (9)	0.0164 (7)	−0.0096 (7)	0.0112 (7)
O31	0.0220 (6)	0.0370 (7)	0.0253 (6)	−0.0013 (5)	−0.0039 (5)	0.0011 (5)
O32	0.0290 (7)	0.0461 (8)	0.0255 (7)	0.0007 (5)	0.0005 (5)	0.0056 (6)
N21	0.0266 (8)	0.0471 (9)	0.0276 (8)	−0.0020 (7)	−0.0027 (6)	−0.0022 (7)
C1	0.0235 (8)	0.0281 (9)	0.0283 (9)	0.0035 (7)	0.0004 (7)	−0.0017 (7)
C2	0.0264 (8)	0.0257 (8)	0.0260 (9)	0.0040 (7)	0.0003 (7)	−0.0020 (7)
C3	0.0255 (9)	0.0331 (10)	0.0393 (11)	−0.0010 (8)	−0.0021 (7)	−0.0033 (8)
C4	0.0299 (10)	0.0362 (10)	0.0499 (13)	−0.0071 (8)	0.0106 (9)	−0.0017 (9)
C5	0.0405 (11)	0.0374 (10)	0.0331 (11)	−0.0045 (8)	0.0097 (8)	0.0035 (8)
C6	0.0340 (10)	0.0415 (11)	0.0281 (9)	0.0024 (8)	−0.0026 (7)	0.0020 (8)
C11	0.0261 (9)	0.0353 (10)	0.0276 (9)	−0.0015 (7)	0.0001 (7)	−0.0008 (7)
C21	0.0266 (9)	0.0435 (11)	0.0334 (10)	−0.0035 (8)	−0.0004 (7)	0.0093 (8)
C31	0.0231 (8)	0.0288 (9)	0.0248 (9)	0.0039 (7)	0.0008 (7)	−0.0028 (7)

Na1—O1W	2.3782 (13)	C1—C2	1.399 (2)
Na1—O2W	2.4404 (17)	C1—C6	1.395 (2)
Na1—O31	2.4370 (13)	C1—C11	1.476 (2)
Na1—O1Wi	2.4162 (13)	C2—C3	1.382 (2)
Na1—O31i	2.5046 (13)	C3—C4	1.371 (3)
Na1—O31ii	2.4577 (13)	C4—C5	1.376 (3)
O21—N21	1.222 (2)	C5—C6	1.374 (3)
O22—N21	1.217 (2)	C11—C21	1.314 (3)
O31—C31	1.267 (2)	C21—C31	1.494 (2)
O32—C31	1.247 (2)	C3—H3	0.9300
O1W—H11W	0.78 (3)	C4—H4	0.9300
O1W—H12W	0.89 (2)	C5—H5	0.9300
O2W—H21W	0.77 (3)	C6—H6	0.9300
O2W—H22W	0.91 (4)	C11—H11	0.9300
N21—C2	1.463 (2)	C21—H21	0.9300
O1W—Na1—O2W	79.67 (5)	C2—C1—C6	115.06 (15)
O1W—Na1—O31	81.96 (4)	C2—C1—C11	123.37 (15)
O1W—Na1—O1Wi	100.64 (4)	C6—C1—C11	121.46 (15)
O1W—Na1—O31i	172.53 (5)	N21—C2—C1	121.34 (14)
O1W—Na1—O31ii	85.02 (4)	N21—C2—C3	115.49 (14)
O2W—Na1—O31	101.58 (6)	C1—C2—C3	123.16 (15)
O1Wi—Na1—O2W	86.43 (5)	C2—C3—C4	119.49 (17)
O2W—Na1—O31i	107.80 (5)	C3—C4—C5	119.26 (18)
O2W—Na1—O31ii	158.48 (6)	C4—C5—C6	120.69 (18)
O1Wi—Na1—O31	171.93 (5)	C1—C6—C5	122.29 (16)
O31—Na1—O31i	96.60 (4)	C1—C11—C21	124.71 (17)
O31—Na1—O31ii	91.04 (4)	C11—C21—C31	124.59 (17)
O1Wi—Na1—O31i	79.83 (4)	O31—C31—C21	115.57 (14)
O1Wi—Na1—O31ii	81.62 (4)	O32—C31—C21	119.48 (15)
O31i—Na1—O31ii	87.68 (4)	O31—C31—O32	124.96 (15)
Na1—O1W—Na1iii	100.64 (5)	C2—C3—H3	120.00
Na1—O31—C31	128.20 (10)	C4—C3—H3	120.00
Na1—O31—Na1iii	96.60 (5)	C3—C4—H4	120.00
Na1—O31—Na1ii	88.96 (4)	C5—C4—H4	120.00
Na1iii—O31—C31	118.92 (10)	C4—C5—H5	120.00
Na1ii—O31—C31	122.84 (10)	C6—C5—H5	120.00
Na1iii—O31—Na1ii	92.32 (4)	C1—C6—H6	119.00
H11W—O1W—H12W	112 (2)	C5—C6—H6	119.00
H21W—O2W—H22W	111 (4)	C1—C11—H11	118.00
O21—N21—C2	118.98 (14)	C21—C11—H11	118.00
O22—N21—C2	117.87 (14)	C11—C21—H21	118.00
O21—N21—O22	123.06 (16)	C31—C21—H21	118.00
O2W—Na1—O1W—Na1iii	95.66 (6)	O31—Na1—O31ii—C31ii	−136.41 (11)
O31—Na1—O1W—Na1iii	−7.75 (5)	Na1—O31—C31—O32	145.52 (13)
O1Wi—Na1—O1W—Na1iii	180.00 (6)	Na1—O31—C31—C21	−35.11 (19)
O31ii—Na1—O1W—Na1iii	−99.51 (5)	Na1iii—O31—C31—O32	−87.48 (18)
O1W—Na1—O31—C31	142.67 (13)	Na1iii—O31—C31—C21	91.89 (14)
O1W—Na1—O31—Na1iii	7.39 (4)	Na1ii—O31—C31—O32	26.8 (2)
O1W—Na1—O31—Na1ii	−84.82 (4)	Na1ii—O31—C31—C21	−153.81 (11)
O2W—Na1—O31—C31	65.02 (14)	O21—N21—C2—C1	−38.6 (2)
O2W—Na1—O31—Na1iii	−70.26 (6)	O21—N21—C2—C3	140.47 (18)
O2W—Na1—O31—Na1ii	−162.47 (5)	O22—N21—C2—C1	144.65 (17)
O31i—Na1—O31—C31	−44.72 (13)	O22—N21—C2—C3	−36.2 (2)
O31i—Na1—O31—Na1iii	180.00 (4)	C6—C1—C2—N21	178.85 (15)
O31i—Na1—O31—Na1ii	87.79 (4)	C6—C1—C2—C3	−0.2 (3)
O31ii—Na1—O31—C31	−132.51 (13)	C11—C1—C2—N21	−4.8 (3)
O31ii—Na1—O31—Na1iii	92.21 (5)	C11—C1—C2—C3	176.18 (17)
O31ii—Na1—O31—Na1ii	0.00 (3)	C2—C1—C6—C5	−1.5 (3)
O1W—Na1—O1Wi—Na1i	−180.00 (6)	C11—C1—C6—C5	−177.99 (17)
O2W—Na1—O1Wi—Na1i	−101.22 (6)	C2—C1—C11—C21	164.51 (18)
O2W—Na1—O31i—Na1i	75.56 (6)	C6—C1—C11—C21	−19.4 (3)
O2W—Na1—O31i—C31i	−65.26 (12)	N21—C2—C3—C4	−177.36 (16)
O31—Na1—O31i—Na1i	180.00 (3)	C1—C2—C3—C4	1.7 (3)
O31—Na1—O31i—C31i	39.19 (12)	C2—C3—C4—C5	−1.6 (3)
O1W—Na1—O31ii—Na1ii	81.83 (4)	C3—C4—C5—C6	−0.1 (3)
O1W—Na1—O31ii—C31ii	−54.58 (11)	C4—C5—C6—C1	1.7 (3)
O2W—Na1—O31ii—Na1ii	126.42 (15)	C1—C11—C21—C31	179.16 (16)
O2W—Na1—O31ii—C31ii	−10.0 (2)	C11—C21—C31—O31	−169.51 (17)
O31—Na1—O31ii—Na1ii	0.00 (5)	C11—C21—C31—O32	9.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O32iv	0.78 (3)	2.14 (3)	2.8871 (17)	162 (2)
O1W—H12W···O32v	0.89 (2)	1.90 (2)	2.7852 (17)	171 (2)
O2W—H21W···O21vi	0.77 (3)	2.49 (3)	3.050 (2)	131 (3)
O2W—H22W···O32iv	0.91 (4)	2.04 (5)	2.882 (2)	153 (4)
C11—H11···O21	0.93	2.39	2.846 (2)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O32i	0.78 (3)	2.14 (3)	2.8871 (17)	162 (2)
O1W—H12W⋯O32ii	0.89 (2)	1.90 (2)	2.7852 (17)	171 (2)
O2W—H21W⋯O21iii	0.77 (3)	2.49 (3)	3.050 (2)	131 (3)
O2W—H22W⋯O32i	0.91 (4)	2.04 (5)	2.882 (2)	153 (4)

Symmetry codes: (i) ; (ii) ; (iii) .