Poly[di­aqua­(μ3-2,3-dioxoindoline-5-sulfonato)­sodium]

Mills-Robles, H.A.; Desikan, V.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2414314617004400

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170440

https://doi.org/10.1107/S2414314617004400

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Poly[diaqua(μ₃-2,3-dioxoindoline-5-sulfonato)sodium]

Heather A. Mills-Robles,^a Vasumathi Desikan,^a James A. Golen ^b and David R. Manke ^b ^*

^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

Edited by M. Weil, Vienna University of Technology, Austria (Received 12 March 2017; accepted 20 March 2017; online 24 March 2017)

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 crystal structure of the title compound. The asymmetric unit comprises a sodium cation, a 2,3-dioxoindoline-5-sulfonate anion and two coordinating water molecules (Fig. 1). 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.

Figure 1
The asymmetric unit of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Figure 2
The coordination environment of the sodium cations in the structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen-bonding interactions are shown as dashed lines.

The 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⋯O7^v hydrogen bond between the isatin amide group and one of the water oxygen atoms. There are also two C—H⋯O interactions, C6—H6⋯O6^vi, between the isatin moiety and a water molecule, and C7—H7⋯O2^vii, 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.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O3ⁱ	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⋯O5ⁱⁱⁱ	0.86 (1)	2.01 (1)	2.854 (2)	169 (2)
O7—H7B⋯O3^iv	0.86 (1)	1.94 (1)	2.780 (2)	168 (3)
N1—H1⋯O7^v	0.87 (1)	1.97 (1)	2.837 (2)	174 (2)
C6—H6⋯O6^vi	0.95	2.63	3.520 (3)	156
C7—H7⋯O2^vii	0.95	2.59	3.453 (3)	152
Symmetry codes: (i) x-1, y, z+1; (ii) x, y, z+1; (iii) -x+2, -y+1, -z+1; (iv) x, y-1, z+1; (v) -x+2, -y+1, -z+2; (vi) x+1, y, z-1; (vii) x+1, y, z.

Figure 3
The crystal packing of the title compound, in a view along the b axis, with hydrogen bonds shown as dashed lines.

The crystal structure of the related sodium 2-oxo-3-semicarbazono-2,3-dihydro-1H-indole-5-sulfonate dihydrate, has been reported previously (Pelosi et al., 2006 ).

Synthesis 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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Na(C₈H₄NO₅S)(H₂O)₂]
M_r	285.20
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	200
a, b, c (Å)	7.4526 (17), 7.9888 (19), 10.692 (2)
α, β, γ (°)	85.916 (10), 80.181 (10), 65.237 (10)
V (Å³)	569.6 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.35
Crystal size (mm)	0.18 × 0.15 × 0.14

Data collection
Diffractometer	Bruker D8 Venture CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.231, 0.259
No. of measured, independent and observed [I > 2σ(I)] reflections	9782, 2142, 1775
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 1.06
No. of reflections	2142
No. of parameters	178
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.41
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1539037

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004400/wm4043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004400/wm4043Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

Poly[diaqua(µ₃-2,3-dioxoindoline-5-sulfonato)sodium] top

Crystal data top

[Na(C₈H₄NO₅S)(H₂O)₂]	Z = 2
M_r = 285.20	F(000) = 292
Triclinic, P1	D_x = 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

Data collection top

Bruker D8 Venture CMOS diffractometer	1775 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 25.7°, θ_min = 3.1°
T_min = 0.231, T_max = 0.259	h = −9→9
9782 measured reflections	k = −9→9
2142 independent reflections	l = −13→13

Refinement top

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(F_o²) + (0.034P)² + 0.4169P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2142 reflections	Δρ_max = 0.37 e Å⁻³
178 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3^iv	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···O5^v	0.86 (1)	2.01 (1)	2.854 (2)	169 (2)
O7—H7B···O3^vi	0.86 (1)	1.94 (1)	2.780 (2)	168 (3)
N1—H1···O7^vii	0.87 (1)	1.97 (1)	2.837 (2)	174 (2)
C6—H6···O6^viii	0.95	2.63	3.520 (3)	156
C7—H7···O2^ix	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 Foundation (award No. CHE-1429086).

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