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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages m1346-m1347
https://doi.org/10.1107/S1600536811035525
ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

Poly[[μ7-L-cysteato(2−)]disodium]

Fu-Hong Liua*

aBasis Department, Jilin Business and Technology College, Hao Yue Road No. 1606, Changchun, Jilin, People's Republic of China
*Correspondence e-mail: liufuhong123@gmail.com

(Received 25 August 2011; accepted 31 August 2011; online 14 September 2011)

The title compound {systematic name: poly[[μ7-(2R)-2-amino-3-sulfonato­propano­ato]disodium]}, [Na2(C3H5NO5S)]n, was obtained through solvent-thermal reaction of L-cysteic acid and aqueous sodium hydroxide. The monomer consists of two Na+ cations that are coordinated to the deprotonated amino acid. The latter acts as donor utilizing all available coordination sites, viz. the amino, the carboxyl­ate and the sulfonate residues, so producing a monomeric framework in which the two coordinated Na+ ions have different coordination spheres and geometries. One of the Na+ ions has an O5 coordination sphere with a typical geometric arrangement, inter­mediate between trigonal–bipyramidal and square–pyramidal; all the O atoms from the amino acid (three from the sulfonate and two from the caboxylate residues) act as donors. The second Na+ ion is tetracoordinated within an NO3 coordination sphere. The Na+ ion binds to the amino N atom, to one of the O atom of the carb­oxy­lic residue and to two O atoms of the sulfonate group in a distorted tetra­hedral arrangement. As the sulfonate O atoms bind to both Na+ ions, a three-dimensional polymeric framework is obtained.

Related literature

For L-cysteic acid in coordination compounds, see: Hendrickson & Karle (1971[Hendrickson, W. A. & Karle, J. (1971). Acta Cryst. B27, 427-431.]); Ramanadham et al. (1973[Ramanadham, M., Sikka, S. K. & Chidambaram, R. (1973). Acta Cryst. B29, 1167-1170.]). For metal-organic frameworks of L-Cysteic acid, see: Bharadwaj et al. (1985[Bharadwaj, P. K., Cohen, B., Zhang, D., Potenza, J. A. & Schugar, H. J. (1985). Acta Cryst. C41, 1033-1035.]); Riley et al. (2002[Riley, P. J., Reid, J. L., Cote, A. P. & Shimizu, G. K. H. (2002). Can. J. Chem. 80, 1584-1591.]); Huang et al. (2009[Huang, F. P., Li, H. Y., Tian, J. L., Gu, W., Jiang, Y. M., Yan, S. P. & Liao, D. Z. (2009). Cryst. Growth Des. 7, 3191-3196.]).

[Scheme 1]

Experimental

Crystal data

  • [Na2(C3H5NO5S)]

  • Mr = 213.13

  • Monoclinic, P 21 /c

  • a = 5.7574 (12) Å

  • b = 11.875 (2) Å

  • c = 11.691 (3) Å

  • β = 109.15 (3)°

  • V = 755.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.52 mm−1

  • T = 298 K

  • 0.24 × 0.22 × 0.20 mm
Data collection

  • Rigaku SCX-MINI diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.885, Tmax = 0.903

  • 7845 measured reflections

  • 1740 independent reflections

  • 1463 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.159

  • S = 1.06

  • 1740 reflections

  • 109 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.94 e Å−3

Table 1
Selected bond lengths (Å)

Na1—O1 2.478 (3)
Na1—O2i 2.427 (3)
Na1—O3 2.415 (4)
Na1—O4ii 2.351 (4)
Na1—O5iii 2.364 (3)
Na2—N1 2.976 (5)
Na2—O3iv 2.905 (5)
Na2—O4 3.028 (5)
Na2—O5iii 2.922 (5)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035525/go2024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035525/go2024Isup2.hkl

checkCIF report


Comment top

Amino acids are of interest in coordination chemistry because they have a large number of highly flexible derivatives capable of forming a wide range of metal compexes. Recently, L-Cysteic acid, (Hendrickson et al., 1971), (Ramanadham et al. 1973) has become an important ligand in the coordination and construction of metal-organic frameworks (MOFs), as a result, some of these frameworks with unusual topologies have been reported by (Bharadwaj et al., 1985, Riley et al., 2002, and Huang et al. 2009). As a part of our work in amino acid coordination research we chose L-Cysteic acid as our ligand. The title compound has recently been prepared in our laboratory and its structure is reported here.

The molecular structure of [C3H5NNa2O5S]n is presented in Fig.1a-c. Fig.1a shows that two Na+ cations are coordinated to one L-Cysteic acid while Fig.1b shows the µ7 connectivity of each L-Cysteic acid. Each L-Cysteic acid chelates one Na+ cation with its O-donor of sulfonate group and of the carboxylate one, and chelates the other Na+ cation with another O-donor from the same sulfonate group and the amine N-donor. Fig.1c shows the coordination environment of the two Na+ cations: for Na1 it is five coordinated while for Na2 forms a 4 coordinated Na node. Moreover, Na1 and Na2 are bridged by one O atom from sulfonyl group. In conclusion, the Na cation and the L-Cysteic acid ligand construct a three-dimensional frameword with space group P21/c, Fig.2.

Related literature top

For L-cysteic acid in coordination compounds, see: Hendrickson & Karle (1971); Ramanadham et al. (1973). For metal-organic frameworks of L-Cysteic acid, see: Bharadwaj et al. (1985); Riley et al. (2002); Huang et al. (2009).

Experimental top

The title complex was synthesized through solvent-thermal reaction by L-Cysteic acid with NaOH aqueous as following method: 84.58 mg (0.5 mmol) of L-Cysteic acid, 10 mL 0.5% NaOH aqueous, were added to a 20 ml Teflon vessel. The vessel was sealed and placed inside a stainless steel autoclave, which was kept at 140°C for 72 h. Then the crystal suiting for X-ray single-crystal analysis was obtained.

Refinement top

H atoms bonded to N atom were located in a difference map and refined with distance restraints of N—H = 0.899–0.900 Å, and with Uiso(H) = 1.2Ueq(N). Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.970–0.981 Å and with Uiso(H) = 1.2 times Ueq(C).

Structure description top

Amino acids are of interest in coordination chemistry because they have a large number of highly flexible derivatives capable of forming a wide range of metal compexes. Recently, L-Cysteic acid, (Hendrickson et al., 1971), (Ramanadham et al. 1973) has become an important ligand in the coordination and construction of metal-organic frameworks (MOFs), as a result, some of these frameworks with unusual topologies have been reported by (Bharadwaj et al., 1985, Riley et al., 2002, and Huang et al. 2009). As a part of our work in amino acid coordination research we chose L-Cysteic acid as our ligand. The title compound has recently been prepared in our laboratory and its structure is reported here.

The molecular structure of [C3H5NNa2O5S]n is presented in Fig.1a-c. Fig.1a shows that two Na+ cations are coordinated to one L-Cysteic acid while Fig.1b shows the µ7 connectivity of each L-Cysteic acid. Each L-Cysteic acid chelates one Na+ cation with its O-donor of sulfonate group and of the carboxylate one, and chelates the other Na+ cation with another O-donor from the same sulfonate group and the amine N-donor. Fig.1c shows the coordination environment of the two Na+ cations: for Na1 it is five coordinated while for Na2 forms a 4 coordinated Na node. Moreover, Na1 and Na2 are bridged by one O atom from sulfonyl group. In conclusion, the Na cation and the L-Cysteic acid ligand construct a three-dimensional frameword with space group P21/c, Fig.2.

For L-cysteic acid in coordination compounds, see: Hendrickson & Karle (1971); Ramanadham et al. (1973). For metal-organic frameworks of L-Cysteic acid, see: Bharadwaj et al. (1985); Riley et al. (2002); Huang et al. (2009).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The ORTEP-3 view of the title complex with atom labels and 50% probability displacement ellipsoids for non-H atoms. a. The asymmetric unit of the title complex. b. The µ7 connectivity of each L-Cysteic acid. Other Na+ cations are hidden for breifness. c. The coordination mode for Na1 and Na2. The other L-Cysteic acid is hidden for breifness.
[Figure 2] Fig. 2. The 2x2x2 packing view of the title complex, viewed down the a axis for non-H atoms.
poly[[µ7-(2R)-2-amino-3-sulfonatopropanoato]disodium] top
Crystal data top
[Na2(C3H5NO5S)]F(000) = 432
Mr = 213.13Dx = 1.875 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7309 reflections
a = 5.7574 (12) Åθ = 3.4–27.5°
b = 11.875 (2) ŵ = 0.52 mm−1
c = 11.691 (3) ÅT = 298 K
β = 109.15 (3)°Prism, colourless
V = 755.1 (3) Å30.24 × 0.22 × 0.20 mm
Z = 4
Data collection top
Rigaku SCX-MINI
diffractometer		1740 independent reflections
Radiation source: fine-focus sealed tube, Rigaku SCX-MINI1463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −7→7
Tmin = 0.885, Tmax = 0.903k = −15→15
7845 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0698P)2 + 2.942P]
where P = (Fo2 + 2Fc2)/3
1740 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.82 e Å−3
0 restraintsΔρmin = −0.94 e Å−3
Crystal data top
[Na2(C3H5NO5S)]V = 755.1 (3) Å3
Mr = 213.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.7574 (12) ŵ = 0.52 mm−1
b = 11.875 (2) ÅT = 298 K
c = 11.691 (3) Å0.24 × 0.22 × 0.20 mm
β = 109.15 (3)°
Data collection top
Rigaku SCX-MINI
diffractometer		1740 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1463 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.903Rint = 0.044
7845 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.06Δρmax = 0.82 e Å−3
1740 reflectionsΔρmin = −0.94 e Å−3
109 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Na20.8052 (6)0.7652 (3)0.4635 (3)0.0831 (9)
Na10.0476 (3)0.74867 (13)0.32535 (13)0.0217 (4)
C10.2111 (7)1.0060 (3)0.3139 (3)0.0182 (7)
C20.4308 (6)1.0333 (3)0.2716 (3)0.0172 (7)
H20.44041.11560.26800.021*
C30.3963 (7)0.9894 (3)0.1434 (3)0.0193 (7)
H3A0.52021.02420.11540.023*
H3B0.23721.01470.09040.023*
N10.6663 (6)0.9944 (3)0.3610 (3)0.0220 (7)
H1A0.78271.01340.32870.026*
H1B0.69041.03960.42570.026*
O10.2379 (5)0.9342 (2)0.3959 (2)0.0237 (6)
O20.0199 (5)1.0610 (2)0.2616 (3)0.0286 (7)
O30.2320 (6)0.7884 (3)0.1716 (3)0.0304 (7)
O40.6639 (5)0.8093 (2)0.1942 (3)0.0293 (7)
O50.3581 (5)0.8235 (2)−0.0035 (2)0.0246 (6)
S10.41314 (16)0.84073 (7)0.12588 (8)0.0166 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na20.081 (2)0.097 (2)0.0771 (19)0.0052 (17)0.0339 (16)0.0134 (17)
Na10.0211 (8)0.0228 (8)0.0202 (8)0.0001 (6)0.0056 (6)0.0015 (6)
C10.0185 (17)0.0158 (17)0.0214 (18)−0.0033 (14)0.0080 (14)−0.0051 (14)
C20.0168 (16)0.0161 (17)0.0210 (17)0.0001 (13)0.0095 (14)0.0002 (13)
C30.0240 (18)0.0179 (17)0.0187 (17)0.0005 (14)0.0104 (15)0.0002 (14)
N10.0144 (14)0.0333 (18)0.0184 (15)−0.0015 (13)0.0054 (12)−0.0058 (13)
O10.0263 (14)0.0257 (14)0.0208 (13)−0.0038 (11)0.0102 (11)0.0012 (11)
O20.0187 (13)0.0296 (15)0.0399 (17)0.0049 (11)0.0128 (12)0.0082 (13)
O30.0358 (17)0.0297 (16)0.0319 (16)−0.0108 (13)0.0195 (14)−0.0023 (13)
O40.0251 (15)0.0282 (15)0.0276 (15)0.0067 (12)−0.0010 (12)−0.0012 (12)
O50.0268 (14)0.0298 (15)0.0180 (13)−0.0052 (11)0.0084 (11)−0.0049 (11)
S10.0180 (4)0.0170 (4)0.0151 (4)−0.0012 (3)0.0059 (3)−0.0006 (3)
Geometric parameters (Å, º) top
Na1—O12.478 (3)C2—N11.488 (5)
Na1—O2i2.427 (3)C2—C31.538 (5)
Na1—O32.415 (4)C2—H20.9800
Na1—O4ii2.351 (4)C3—S11.783 (4)
Na1—O5iii2.364 (3)C3—H3A0.9700
Na2—N12.976 (5)C3—H3B0.9700
Na2—O3iv2.905 (5)N1—H1A0.9000
Na2—O43.028 (5)N1—H1B0.9000
Na2—O5iii2.922 (5)O3—S11.457 (3)
C1—O21.253 (5)O4—S11.451 (3)
C1—O11.254 (5)O5—S11.455 (3)
C1—C21.537 (5)
O1—Na1—O5iii84.93 (10)C1—C2—H2106.7
O1—Na1—O379.62 (12)C3—C2—H2106.7
O3—Na1—O4ii90.18 (13)C2—C3—S1117.0 (3)
O4ii—Na1—O5iii162.00 (13)C2—C3—H3A108.1
O3iv—Na2—N1125.41 (16)S1—C3—H3A108.1
O3iv—Na2—O4140.68 (16)C2—C3—H3B108.1
O3iv—Na2—O5iii110.50 (14)S1—C3—H3B108.1
O4—Na2—N158.54 (11)H3A—C3—H3B107.3
O4—Na2—O5iii104.59 (13)C2—N1—H1A105.0
O5iii—Na2—N1104.53 (14)C2—N1—H1B105.0
O2—C1—O1126.6 (3)H1A—N1—H1B105.9
O2—C1—C2114.6 (3)O4—S1—O5111.96 (17)
O1—C1—C2118.8 (3)O4—S1—O3113.02 (19)
N1—C2—C1111.4 (3)O5—S1—O3112.53 (17)
N1—C2—C3112.1 (3)O4—S1—C3105.86 (18)
C1—C2—C3112.7 (3)O5—S1—C3104.89 (17)
N1—C2—H2106.7O3—S1—C3107.93 (17)
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2; (iv) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Na2(C3H5NO5S)]
Mr213.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.7574 (12), 11.875 (2), 11.691 (3)
β (°) 109.15 (3)
V (Å3)755.1 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.52
Crystal size (mm)0.24 × 0.22 × 0.20
Data collection
DiffractometerRigaku SCX-MINI
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.885, 0.903
No. of measured, independent and
observed [I > 2σ(I)] reflections		7845, 1740, 1463
Rint0.044
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.159, 1.06
No. of reflections1740
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.82, −0.94

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Na1—O12.478 (3)Na2—N12.976 (5)
Na1—O2i2.427 (3)Na2—O3iv2.905 (5)
Na1—O32.415 (4)Na2—O43.028 (5)
Na1—O4ii2.351 (4)Na2—O5iii2.922 (5)
Na1—O5iii2.364 (3)
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2; (iv) x+1, −y+3/2, z+1/2.
 

Acknowledgements

The author thanks Jilin Business and Technology College for financial support.

References

First citationBharadwaj, P. K., Cohen, B., Zhang, D., Potenza, J. A. & Schugar, H. J. (1985). Acta Cryst. C41, 1033–1035.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationHendrickson, W. A. & Karle, J. (1971). Acta Cryst. B27, 427–431.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationHuang, F. P., Li, H. Y., Tian, J. L., Gu, W., Jiang, Y. M., Yan, S. P. & Liao, D. Z. (2009). Cryst. Growth Des. 7, 3191–3196.  Web of Science CSD CrossRef Google Scholar
 First citationRamanadham, M., Sikka, S. K. & Chidambaram, R. (1973). Acta Cryst. B29, 1167–1170.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationRiley, P. J., Reid, J. L., Cote, A. P. & Shimizu, G. K. H. (2002). Can. J. Chem. 80, 1584–1591.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages m1346-m1347
https://doi.org/10.1107/S1600536811035525
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