metal-organic compounds
Poly[diaqua(μ3-2,3-dioxoindoline-5-sulfonato)sodium]
aDepartment of Science & Math, Massasoit Community College, 1 Massasoit Boulevard, Brockton, MA 02302, USA, and bDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA
*Correspondence e-mail: dmanke@umassd.edu
The title compound, [Na(C8H4NO5S)(H2O)2]n, is a one-dimensional coordination polymer extending along the c axis. It consist of isatin sulfonate molecules linking pairs of sodium cations with Na—O bonds to both carbonyl and sulfonate oxygen atoms whereby two oxygen atoms of symmetry-related carbonyl groups bridge two sodium cations. The sodium cation possesses an octahedral coordination environment, including one sulfonate and three carbonyl oxygen atoms bound in the equatorial plane, and two water molecules bound axially. The isatin moiety of the organic ligand is nearly planar, with a mean deviation from planarity of 0.038 Å. The chains of the coordination polymer are further linked into a three-dimensional network with eight distinct interactions, including one N—H⋯O and four O—H⋯O hydrogen bonds, two C—H⋯O interactions and one π–π interaction.
Keywords: crystal structure; coordination polymer; isatin; hydrogen bonding; π–π interactions.
CCDC reference: 1539037
Structure description
As part of our standing project to study the crystal structures of N-H isatins, we report the ). The isatin moiety of the anion is nearly planar. The sodium cation possesses an octahedral configuration, and is coordinated by three carbonyl oxygen atoms, two water molecules, and one sulfonate oxygen atom. Two symmetry-related O1 carbonyl oxygen atoms bridge two sodium cations, with the O2 carbonyl oxygen binding to only a single sodium cation. The O5 sulfonate oxygen atom and the two water oxygen atoms (O6, O7) complete the sodium coordination environment (Fig. 2). Despite the coordination of the carbonyl oxygen atoms to the sodium cations, the C=O bonds and other metric parameters are consistent with those in neutral 5-substituted isatins (Gurung et al., 2016). Pairs of sodium cations are linked by the isatin molecules to form a one-dimensional coordination polymer along the c axis.
of the title compound. The comprises a sodium cation, a 2,3-dioxoindoline-5-sulfonate anion and two coordinating water molecules (Fig. 1The sodium–isatin chains are interconnected by a series of hydrogen bonds and π–π interactions to combine into a three-dimensional network. There is an N1—H1⋯O7v hydrogen bond between the isatin amide group and one of the water oxygen atoms. There are also two C—H⋯O interactions, C6—H6⋯O6vi, between the isatin moiety and a water molecule, and C7—H7⋯O2vii, between the isatin moiety and the carbonyl oxygen atom of another isatin moiety (see Table 1 for symmetry codes). Both of the water molecules are involved in two O—H⋯O interactions to sulfonate oxygen atoms of the same chain and neighboring chains (Fig. 2). The chains are further linked between the aromatic six-membered rings in the isatin moieties, with parallel slipped π–π interactions [intercentroid distance = 3.8314 (19) Å, interplanar distance = 3.619 (2) Å and slippage = 1.259 (4) Å]. The molecular packing of the title compound with hydrogen bonding is shown in Fig. 3.
The H-indole-5-sulfonate dihydrate, has been reported previously (Pelosi et al., 2006).
of the related sodium 2-oxo-3-semicarbazono-2,3-dihydro-1Synthesis and crystallization
A commercial sample (Combi-Blocks) of sodium 2,3-dioxoindole-5-sulfonate dihydrate was recrystallized by slow evaporation of an ethanol–water solution to yield orange blocks suitable for single-crystal X-ray diffraction analysis.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1539037
https://doi.org/10.1107/S2414314617004400/wm4043sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004400/wm4043Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).[Na(C8H4NO5S)(H2O)2] | Z = 2 |
Mr = 285.20 | F(000) = 292 |
Triclinic, P1 | Dx = 1.663 Mg m−3 |
a = 7.4526 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9888 (19) Å | Cell parameters from 4084 reflections |
c = 10.692 (2) Å | θ = 3.2–25.7° |
α = 85.916 (10)° | µ = 0.35 mm−1 |
β = 80.181 (10)° | T = 200 K |
γ = 65.237 (10)° | BLOCK, orange |
V = 569.6 (2) Å3 | 0.18 × 0.15 × 0.14 mm |
Bruker D8 Venture CMOS diffractometer | 1775 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.043 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 25.7°, θmin = 3.1° |
Tmin = 0.231, Tmax = 0.259 | h = −9→9 |
9782 measured reflections | k = −9→9 |
2142 independent reflections | l = −13→13 |
Refinement on F2 | 5 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.4169P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2142 reflections | Δρmax = 0.37 e Å−3 |
178 parameters | Δρmin = −0.41 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Na1 | 0.62093 (12) | 0.56376 (12) | 1.11207 (8) | 0.0228 (2) | |
S1 | 0.77858 (8) | 0.88556 (7) | 0.21370 (5) | 0.01699 (15) | |
O1 | 0.6277 (2) | 0.5579 (2) | 0.89024 (14) | 0.0258 (4) | |
O2 | 0.4366 (2) | 0.5933 (2) | 0.66757 (14) | 0.0280 (4) | |
O3 | 0.9274 (2) | 0.9597 (2) | 0.17078 (14) | 0.0247 (4) | |
O4 | 0.5735 (2) | 1.0224 (2) | 0.21817 (14) | 0.0242 (4) | |
O5 | 0.8185 (2) | 0.7209 (2) | 0.14265 (13) | 0.0214 (3) | |
O6 | 0.3464 (3) | 0.8278 (3) | 1.1862 (2) | 0.0443 (5) | |
H6A | 0.231 (2) | 0.873 (4) | 1.162 (3) | 0.066* | |
H6B | 0.384 (5) | 0.916 (3) | 1.186 (3) | 0.066* | |
O7 | 0.9207 (2) | 0.3007 (2) | 1.09034 (14) | 0.0229 (4) | |
H7A | 0.990 (3) | 0.288 (4) | 1.0162 (11) | 0.034* | |
H7B | 0.911 (4) | 0.1986 (19) | 1.108 (2) | 0.034* | |
N1 | 0.8411 (3) | 0.6490 (3) | 0.74783 (17) | 0.0210 (4) | |
H1 | 0.918 (3) | 0.656 (3) | 0.7979 (17) | 0.025* | |
C1 | 0.6827 (3) | 0.6067 (3) | 0.78595 (19) | 0.0191 (5) | |
C2 | 0.5776 (3) | 0.6315 (3) | 0.6672 (2) | 0.0203 (5) | |
C3 | 0.6918 (3) | 0.7000 (3) | 0.56743 (19) | 0.0186 (5) | |
C4 | 0.6678 (3) | 0.7541 (3) | 0.44351 (19) | 0.0190 (4) | |
H4 | 0.5608 | 0.7514 | 0.4077 | 0.023* | |
C5 | 0.8064 (3) | 0.8129 (3) | 0.37292 (19) | 0.0177 (4) | |
C6 | 0.9651 (3) | 0.8131 (3) | 0.4255 (2) | 0.0234 (5) | |
H6 | 1.0593 | 0.8509 | 0.3747 | 0.028* | |
C7 | 0.9891 (3) | 0.7594 (3) | 0.5508 (2) | 0.0239 (5) | |
H7 | 1.0972 | 0.7601 | 0.5863 | 0.029* | |
C8 | 0.8495 (3) | 0.7053 (3) | 0.62055 (19) | 0.0188 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0220 (5) | 0.0256 (5) | 0.0235 (5) | −0.0123 (4) | −0.0040 (3) | −0.0007 (4) |
S1 | 0.0172 (3) | 0.0175 (3) | 0.0177 (3) | −0.0089 (2) | −0.0020 (2) | 0.0010 (2) |
O1 | 0.0319 (9) | 0.0317 (9) | 0.0193 (8) | −0.0188 (8) | −0.0061 (7) | 0.0062 (7) |
O2 | 0.0298 (9) | 0.0396 (10) | 0.0264 (8) | −0.0258 (8) | −0.0063 (7) | 0.0036 (7) |
O3 | 0.0255 (9) | 0.0275 (9) | 0.0275 (8) | −0.0182 (8) | −0.0033 (7) | 0.0057 (7) |
O4 | 0.0201 (8) | 0.0217 (8) | 0.0281 (8) | −0.0056 (7) | −0.0046 (6) | 0.0003 (7) |
O5 | 0.0243 (8) | 0.0212 (8) | 0.0197 (8) | −0.0110 (7) | −0.0006 (6) | −0.0038 (6) |
O6 | 0.0222 (10) | 0.0353 (11) | 0.0768 (14) | −0.0125 (9) | −0.0070 (9) | −0.0070 (10) |
O7 | 0.0275 (9) | 0.0235 (9) | 0.0204 (8) | −0.0140 (8) | −0.0016 (6) | −0.0003 (7) |
N1 | 0.0203 (10) | 0.0278 (10) | 0.0191 (9) | −0.0126 (9) | −0.0077 (7) | 0.0027 (8) |
C1 | 0.0211 (12) | 0.0171 (11) | 0.0198 (11) | −0.0078 (10) | −0.0045 (9) | −0.0009 (9) |
C2 | 0.0214 (12) | 0.0201 (11) | 0.0205 (11) | −0.0097 (10) | −0.0035 (9) | −0.0002 (9) |
C3 | 0.0180 (11) | 0.0197 (11) | 0.0202 (11) | −0.0097 (9) | −0.0028 (8) | −0.0001 (9) |
C4 | 0.0178 (11) | 0.0218 (11) | 0.0208 (11) | −0.0108 (10) | −0.0045 (8) | −0.0012 (9) |
C5 | 0.0189 (11) | 0.0166 (11) | 0.0180 (10) | −0.0083 (9) | −0.0009 (8) | −0.0016 (8) |
C6 | 0.0216 (12) | 0.0277 (13) | 0.0252 (12) | −0.0155 (11) | −0.0017 (9) | 0.0014 (9) |
C7 | 0.0190 (12) | 0.0328 (13) | 0.0252 (12) | −0.0151 (11) | −0.0057 (9) | 0.0006 (10) |
C8 | 0.0173 (11) | 0.0188 (11) | 0.0196 (11) | −0.0060 (9) | −0.0046 (8) | −0.0008 (8) |
Na1—Na1i | 3.6590 (17) | O6—H6B | 0.860 (5) |
Na1—O1 | 2.3669 (17) | O7—H7A | 0.857 (5) |
Na1—O1i | 2.4309 (18) | O7—H7B | 0.856 (5) |
Na1—O2i | 2.6444 (18) | N1—H1 | 0.867 (5) |
Na1—O5ii | 2.3706 (17) | N1—C1 | 1.351 (3) |
Na1—O6 | 2.309 (2) | N1—C8 | 1.402 (3) |
Na1—O7 | 2.3283 (19) | C1—Na1i | 3.113 (2) |
Na1—C1i | 3.113 (2) | C1—C2 | 1.561 (3) |
S1—O3 | 1.4596 (15) | C2—C3 | 1.470 (3) |
S1—O4 | 1.4547 (16) | C3—C4 | 1.382 (3) |
S1—O5 | 1.4609 (15) | C3—C8 | 1.406 (3) |
S1—C5 | 1.777 (2) | C4—H4 | 0.9500 |
O1—Na1i | 2.4309 (18) | C4—C5 | 1.395 (3) |
O1—C1 | 1.216 (2) | C5—C6 | 1.395 (3) |
O2—Na1i | 2.6444 (18) | C6—H6 | 0.9500 |
O2—C2 | 1.210 (3) | C6—C7 | 1.394 (3) |
O5—Na1iii | 2.3707 (17) | C7—H7 | 0.9500 |
O6—H6A | 0.858 (5) | C7—C8 | 1.376 (3) |
O1i—Na1—Na1i | 39.66 (4) | S1—O5—Na1iii | 133.64 (9) |
O1—Na1—Na1i | 40.95 (4) | Na1—O6—H6A | 127 (2) |
O1—Na1—O1i | 80.61 (6) | Na1—O6—H6B | 109 (2) |
O1—Na1—O2i | 145.72 (6) | H6A—O6—H6B | 107 (3) |
O1i—Na1—O2i | 69.98 (5) | Na1—O7—H7A | 113.6 (18) |
O1—Na1—O5ii | 106.21 (6) | Na1—O7—H7B | 115.7 (18) |
O1i—Na1—C1i | 21.08 (5) | H7A—O7—H7B | 107 (3) |
O1—Na1—C1i | 101.52 (6) | C1—N1—H1 | 124.4 (15) |
O2i—Na1—Na1i | 107.88 (5) | C1—N1—C8 | 111.27 (17) |
O2i—Na1—C1i | 49.33 (5) | C8—N1—H1 | 123.8 (16) |
O5ii—Na1—Na1i | 146.48 (5) | O1—C1—Na1i | 45.97 (11) |
O5ii—Na1—O1i | 169.43 (6) | O1—C1—N1 | 128.8 (2) |
O5ii—Na1—O2i | 105.59 (6) | O1—C1—C2 | 124.92 (19) |
O5ii—Na1—C1i | 151.73 (6) | N1—C1—Na1i | 168.95 (15) |
O6—Na1—Na1i | 96.15 (6) | N1—C1—C2 | 106.28 (17) |
O6—Na1—O1i | 83.70 (7) | C2—C1—Na1i | 79.79 (11) |
O6—Na1—O1 | 106.17 (8) | O2—C2—C1 | 122.89 (19) |
O6—Na1—O2i | 88.14 (7) | O2—C2—C3 | 132.4 (2) |
O6—Na1—O5ii | 86.60 (7) | C3—C2—C1 | 104.67 (17) |
O6—Na1—O7 | 164.59 (8) | C4—C3—C2 | 132.34 (19) |
O6—Na1—C1i | 80.47 (7) | C4—C3—C8 | 121.11 (19) |
O7—Na1—Na1i | 97.83 (5) | C8—C3—C2 | 106.56 (18) |
O7—Na1—O1i | 103.12 (6) | C3—C4—H4 | 121.2 |
O7—Na1—O1 | 88.71 (6) | C3—C4—C5 | 117.57 (19) |
O7—Na1—O2i | 81.43 (6) | C5—C4—H4 | 121.2 |
O7—Na1—O5ii | 85.33 (6) | C4—C5—S1 | 118.75 (16) |
O7—Na1—C1i | 100.84 (6) | C6—C5—S1 | 120.41 (16) |
C1i—Na1—Na1i | 60.61 (5) | C6—C5—C4 | 120.84 (19) |
O3—S1—O5 | 111.89 (9) | C5—C6—H6 | 119.2 |
O3—S1—C5 | 106.05 (9) | C7—C6—C5 | 121.68 (19) |
O4—S1—O3 | 113.46 (9) | C7—C6—H6 | 119.2 |
O4—S1—O5 | 112.52 (9) | C6—C7—H7 | 121.4 |
O4—S1—C5 | 106.06 (9) | C8—C7—C6 | 117.12 (19) |
O5—S1—C5 | 106.17 (9) | C8—C7—H7 | 121.4 |
Na1—O1—Na1i | 99.39 (6) | N1—C8—C3 | 111.14 (18) |
C1—O1—Na1 | 146.85 (15) | C7—C8—N1 | 127.21 (19) |
C1—O1—Na1i | 112.95 (14) | C7—C8—C3 | 121.65 (19) |
C2—O2—Na1i | 107.73 (14) | ||
Na1—O1—C1—Na1i | −166.5 (3) | N1—C1—C2—O2 | 175.3 (2) |
Na1—O1—C1—N1 | 26.5 (4) | N1—C1—C2—C3 | −3.0 (2) |
Na1i—O1—C1—N1 | −166.99 (19) | C1—N1—C8—C3 | −0.7 (3) |
Na1i—O1—C1—C2 | 12.7 (3) | C1—N1—C8—C7 | 179.6 (2) |
Na1—O1—C1—C2 | −153.79 (19) | C1—C2—C3—C4 | −177.2 (2) |
Na1i—O2—C2—C1 | −5.9 (2) | C1—C2—C3—C8 | 2.5 (2) |
Na1i—O2—C2—C3 | 171.9 (2) | C2—C3—C4—C5 | −179.8 (2) |
Na1i—C1—C2—O2 | 4.8 (2) | C2—C3—C8—N1 | −1.3 (2) |
Na1i—C1—C2—C3 | −173.49 (15) | C2—C3—C8—C7 | 178.4 (2) |
S1—C5—C6—C7 | 179.05 (17) | C3—C4—C5—S1 | −179.40 (16) |
O1—C1—C2—O2 | −4.4 (3) | C3—C4—C5—C6 | 1.2 (3) |
O1—C1—C2—C3 | 177.3 (2) | C4—C3—C8—N1 | 178.46 (19) |
O2—C2—C3—C4 | 4.7 (4) | C4—C3—C8—C7 | −1.8 (3) |
O2—C2—C3—C8 | −175.5 (2) | C4—C5—C6—C7 | −1.6 (3) |
O3—S1—O5—Na1iii | −161.56 (11) | C5—S1—O5—Na1iii | 83.17 (13) |
O3—S1—C5—C4 | 173.02 (16) | C5—C6—C7—C8 | 0.2 (3) |
O3—S1—C5—C6 | −7.6 (2) | C6—C7—C8—N1 | −178.9 (2) |
O4—S1—O5—Na1iii | −32.43 (14) | C6—C7—C8—C3 | 1.5 (3) |
O4—S1—C5—C4 | 52.08 (19) | C8—N1—C1—Na1i | 124.4 (7) |
O4—S1—C5—C6 | −128.54 (18) | C8—N1—C1—O1 | −178.0 (2) |
O5—S1—C5—C4 | −67.82 (19) | C8—N1—C1—C2 | 2.3 (2) |
O5—S1—C5—C6 | 111.56 (18) | C8—C3—C4—C5 | 0.4 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y, z+1; (iii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O3iv | 0.86 (1) | 2.06 (1) | 2.878 (2) | 159 (3) |
O6—H6B···O4ii | 0.86 (1) | 2.01 (2) | 2.807 (2) | 153 (3) |
O7—H7A···O5v | 0.86 (1) | 2.01 (1) | 2.854 (2) | 169 (2) |
O7—H7B···O3vi | 0.86 (1) | 1.94 (1) | 2.780 (2) | 168 (3) |
N1—H1···O7vii | 0.87 (1) | 1.97 (1) | 2.837 (2) | 174 (2) |
C6—H6···O6viii | 0.95 | 2.63 | 3.520 (3) | 156 |
C7—H7···O2ix | 0.95 | 2.59 | 3.453 (3) | 152 |
Symmetry codes: (ii) x, y, z+1; (iv) x−1, y, z+1; (v) −x+2, −y+1, −z+1; (vi) x, y−1, z+1; (vii) −x+2, −y+1, −z+2; (viii) x+1, y, z−1; (ix) x+1, y, z. |
Funding information
Funding for this research was provided by: Massachusetts Clean Energy Center; National Science Foundationhttps://doi.org/10.13039/100000001 (award No. CHE-1429086).
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