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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 69| Part 12| December 2013| Pages m670-m671
doi:10.1107/S1600536813031255

Poly[bis­­(μ2-1,3-phenyl­enedi­amine-κ2N:N′)di-μ-thio­cyanato-κ2N:S;κ2S:N-cadmium]

Rakia Chemli,a* Slaheddine Kamouna and Thierry Roisnelb

aLaboratoire de Génie des Matériaux et Environnement, École Nationale d'Ingénieurs de Sfax, BP 1173, Sfax, Tunisia, and bCentre de Diffractométrie X, UMR 6226 CNRS Unité des Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
*Correspondence e-mail: rakya.chamli@gmail.com

(Received 1 November 2013; accepted 14 November 2013; online 20 November 2013)

The structure of the title polymeric compound, [Cd(SCN)2(C6H8N2)2]n, exhibits a two-dimensional staircase-like structure parallel to (010) in which the CdII atom lies on a twofold rotation axis and has a distorted octa­hedral CdS2N4 geometry involving four μ-1,3-(SCN) group donors and two N-atom donors from 1,3-phenyl­enedi­amine ligands, which also have twofold symmetry. The major contributions to the cohesion and the stability of this two-dimensional polymeric structure are the covalent Cd—S,N bonds and one weak intra­layer N—H⋯S hydrogen bond.

CCDC reference: 971936

Related literature

For related structures, see: MacGillivary et al. (1994[MacGillivary, L. R., Subramamian, S. & Zaworotko, M. J. (1994). J. Chem. Soc. Chem. Commun. pp. 1325-1326.]); Fujita et al. (1995[Fujita, M., Kwan, Y. J., Sataki, O., Yamaguchi, K. & Ogura, K. (1995). J. Am. Chem. Soc. 117, 7287-7288.]); Blake et al. (1997[Blake, A. J., Champness, N. R., Khlobystov, A., Lemenovskii, D. A., Li, W.-S. & Schroder, M. (1997). Chem. Commun. pp. 2027-2028.]); Withersby et al. (1997[Withersby, M. A., Blake, A. J., Champness, N. R., Hubberstey, P., Li, W.-S. & Schroder, M. (1997). Angew. Chem. Int. Ed. Engl. 36, 2327-2329.]); Tong et al. (1998[Tong, M.-L., Ye, B.-H., Cai, J.-W. & Chen, X.-M. (1998). Inorg. Chem. 37, 2645-2650.]); Yang et al. (2001[Yang, G., Zhu, H.-G., Liang, B.-H. & Chen, X.-M. (2001). J. Chem. Soc. Dalton Trans. pp. 580-585.]); Chemli et al. (2013[Chemli, R., Kamoun, S. & Roisnel, T. (2013). Acta Cryst. E69, m292-m293.]). For the HSCN synthesis, see: Bartlett et al. (1969[Bartlett, H. E., Jurriaanse, A. & De Haas, K. (1969). Can. J. Chem. 47, 16, 2981-2986.]). For the effects of substituents on the inter­nal angles of the phenyl ring, see: Domenicano & Murray-Rust (1979[Domenicano, A. & Murray-Rust, P. (1979). Tetrahedron Lett. 24, 2283-2286.]). For NLO and luminescence of related compounds, see: Chen et al. (2000[Chen, H., Zhang, L., Cai, Z., Guang Yanga, G. & Chen, X. (2000). J. Chem. Soc. Dalton Trans. pp. 2463-2466.]); Bai et al. (2011[Bai, Y., Hu, X., Dang, D., Bi, F. & Niu, J. (2011). Spectrochim. Acta, 78, 70-73.]). For electric and dielectric properties of related compounds, see: Karoui et al. (2013[Karoui, S., Kamoun, S. & Jouini, A. (2013). J. Solid State Chem. 197, 60-68.]).

[Scheme 1]

Experimental

Crystal data

  • [Cd(NCS)2(C6H8N2)2]

  • Mr = 336.7

  • Monoclinic, C 2/c

  • a = 10.8704 (6) Å

  • b = 12.8983 (10) Å

  • c = 8.3362 (5) Å

  • β = 106.503 (3)°

  • V = 1120.67 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.29 mm−1

  • T = 150 K

  • 0.17 × 0.07 × 0.06 mm
Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.825, Tmax = 0.872

  • 4396 measured reflections

  • 1283 independent reflections

  • 1130 reflections with I > 2σ(I)

  • Rint = 0.061
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.064

  • S = 1.03

  • 1283 reflections

  • 70 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Selected bond lengths (Å)

Cd1—N1i 2.306 (3)
Cd1—N2 2.364 (3)
Cd1—S1 2.7143 (10)
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2B⋯S1iii 0.92 2.67 3.589 (3) 173
Symmetry code: (iii) [x, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.] and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 971936

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813031255/vn2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031255/vn2078Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031255/vn2078Isup3.cdx

checkCIF report


Comment top

The crystal engineering of inorganic-organic hybrid coordination polymers is currently one of the most active fields in coordination chemistry, supramolecular and materials chemistry. These compounds attract significant attention for their architectures and topologies (Yang et al., 2001), including a large number of extended assemblies such as helical network (Withersby et al., 1997; Chemli et al. 2013) molecular zippers, diamondoid, honeycomb (Tong et al., 1998), square- grid (MacGillivary et al., 1994), T-shaped and ladder frameworks. (Fujita et al., 1995; Blake et al.,1997). Hybrid inorganic-organic thiocyanate materials exhibit interesting physical properties such electrical conductivity and dielectric relaxation process (Karoui et al., 2013) and may have potential applications in non-linear optics and luminescence (Chen et al., 2000; Bai et al., 2011). Herein we report the structure of a new polymeric hybrid [Cd(SCN)2(C6H8N2)2]n. As shown in Fig. 1, each cadmium atom, which sits on a twofold rotation axis, is coordinated by two cis N-bonded and two cis S-bonded thiocyanato anions. Two trans-coordinated neutral m-phenylenediamine ligands complete the octahedral coordination geometry around cadmium. The crystal structure of the title compound consists of both doubly µ-1,3-SCN and µ-1,3-phenylendiamine –bridged two-dimensional networks (Fig. 2). In the CdN4S2 core, the Cd—N and Cd—S bonds are in the range 2.3061 - 2.364 (3) Å and 2.7143 (10) Å, respectively (Table 1). The bond angles involving the cadmium (II) atom range from 83.89 (11) to 96.91 (10)° and from 174.75 (8) to 178.87 (14)°. These values are in good agreement with those observed in other similar complexes (Chemli et al. 2013). The double SCN bridging mode gives rise to a centrosymmetrical eight-membered Cd(SCN)2Cd rings in a chair conformation because of the almost linear SCN groups (S–C–N angle = 178.8 (3)°). The distance between adjacent Cd atoms in Cd2 (SCN)2 rings is 5.937 Å. Again, these rings built up a staircase-like chain through their corner-sharing action at the two cadmium atoms via the µ-1,3-phenylenediamine moiety and give rise to twenty-membered [Cd4(µ-1,3-SCN)4(µ-1,3-phenylendiamine)2] macrocycles as subunits, as depicted in Fig. 2. The bond angles in the phenyl groups deviate significantly from the idealized value of 120° due to the effect of the substituent. In fact, it was established that the angular deformations of phenyl groups can be described as a sum of the effects of the different substituents (Domenicano & Murray-Rust, 1979). The phenyl rings of 1,3-phenylendiamine ligand are planar with the greatest deviation from the six-atoms least-square plane of 0.0001 Å. They are well ordered with C–C–C angles in agreement with the expected sp2 hybridization. The π-π interactions between neighboring phenyl rings may be neglected (>4 Å). The major contributions of the cohesion and the stability of this polymeric structure is assured by the covalent Cd-(S,N) bonds and the presence of one weak intralayer N–H···S hydrogen bond with the H···S and N···S distances of 2.674 Å and 3.589 (3) Å, respectively (Table 2).

Related literature top

For related structures, see: MacGillivary et al. (1994); Fujita et al. (1995); Blake et al. (1997); Withersby et al. (1997); Tong et al. (1998); Yang et al. (2001); Chemli et al. (2013). For the HSCN synthesis, see Bartlett et al. (1969). For the effects of substituents on the internal angles of the phenyl ring, see: Domenicano & Murray-Rust (1979). For NLO and luminescence of related compounds, see Chen et al. (2000); Bai et al. (2011). For electric and dielectric properties of related compounds, see: Karoui et al. (2013).

Experimental top

To 25 ml of an aqueous solution of thiocyanic acid (0.4 mol.l-1) prepared using the published procedure (Bartlett et al., 1969) an appropriate amount of cadmium carbonate (0.832 g, 5 mmol) was added and refluxed for 2 h. After cooling, 25 ml of methanol and 0.7 ml of a solution of 1,3-phenylenediamine (7.5 mol.l-1) was added. The resulting solution was heated under reflux for 2 h and left at ambient temperature for 2 hours after which well shaped brown crystals were obtained on slow evaporation of the solvent. They were washed with diethyl ether and dried over P2O5.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.98 Å, N—H = 0.92 Å, and with Uiso(H) = 1.2Ueq(C, N).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the coordination around the Cd2+ cations with labelling and displacement ellipsoids drawn at the 50% probability level. The H atoms are omitted for clarity. Symmetry codes: (i):-x + 3/2, -y + 1/2, -z + 1; (ii):x - 1/2, -y + 1/2, z - 1/2;(iii):-x + 1, y, -z + 1/2; (iv):-x + 1, y, -z - 1/2
[Figure 2] Fig. 2. The two-dimensional molecular structure of the title coordination polymer showing the staircase molecular arrangement.
Poly[bis(µ2-1,3-phenylenediamine-κ2N:N')di-µ-thiocyanato-κ2N:S;κ2S:N-cadmium] top
Crystal data top
[Cd(NCS)2(C6H8N2)2]F(000) = 656
Mr = 336.7Dx = 1.996 Mg m−3
Dm = 1.931 Mg m−3
Dm measured by Flotation
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1283 reflections
a = 10.8704 (6) Åθ = 3.2–27.5°
b = 12.8983 (10) ŵ = 2.29 mm−1
c = 8.3362 (5) ÅT = 150 K
β = 106.503 (3)°Prism, brown
V = 1120.67 (13) Å30.17 × 0.07 × 0.06 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		1130 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
CCD rotation images, thin slices scansh = −10→14
Absorption correction: multi-scan
(SADABS; Bruker, 2011)		k = −16→16
Tmin = 0.825, Tmax = 0.872l = −10→9
4396 measured reflections2 standard reflections every 120 min
1283 independent reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0156P)2]
where P = (Fo2 + 2Fc2)/3
1283 reflections(Δ/σ)max < 0.001
70 parametersΔρmax = 0.60 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[Cd(NCS)2(C6H8N2)2]V = 1120.67 (13) Å3
Mr = 336.7Z = 4
Monoclinic, C2/cMo Kα radiation
a = 10.8704 (6) ŵ = 2.29 mm−1
b = 12.8983 (10) ÅT = 150 K
c = 8.3362 (5) Å0.17 × 0.07 × 0.06 mm
β = 106.503 (3)°
Data collection top
Bruker APEXII
diffractometer		1283 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)		1130 reflections with I > 2σ(I)
Tmin = 0.825, Tmax = 0.872Rint = 0.061
4396 measured reflections2 standard reflections every 120 min
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.064H-atom parameters constrained
S = 1.03Δρmax = 0.60 e Å−3
1283 reflectionsΔρmin = −0.58 e Å−3
70 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
Cd10.50.20749 (3)0.250.01462 (12)
S10.65559 (10)0.05195 (8)0.40889 (13)0.0297 (3)
N10.8532 (3)0.1670 (2)0.6240 (4)0.0219 (7)
C10.7707 (3)0.1202 (3)0.5352 (4)0.0163 (8)
N20.6151 (3)0.2057 (2)0.0483 (4)0.0191 (7)
H2A0.69520.2330.09680.023*
H2B0.62630.13770.02230.023*
C20.5594 (3)0.2606 (3)−0.1055 (4)0.0159 (8)
C30.50.2075 (4)−0.250.0149 (10)
H30.50.1339−0.250.018*
C40.5598 (3)0.3684 (3)−0.1044 (4)0.0174 (8)
H40.60070.4054−0.00490.021*
C50.50.4211 (4)−0.250.0237 (13)
H50.50.4947−0.250.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0134 (2)0.0146 (2)0.0142 (2)00.00127 (14)0
S10.0252 (6)0.0127 (5)0.0371 (6)−0.0027 (4)−0.0140 (4)0.0019 (4)
N10.0209 (18)0.0165 (17)0.0248 (18)0.0001 (14)0.0010 (15)0.0012 (14)
C10.0176 (19)0.0127 (19)0.0180 (19)0.0044 (16)0.0041 (15)0.0024 (15)
N20.0182 (16)0.0191 (17)0.0199 (17)0.0006 (14)0.0051 (13)−0.0011 (14)
C20.0117 (18)0.021 (2)0.0168 (19)0.0008 (15)0.0067 (15)0.0013 (15)
C30.013 (2)0.012 (3)0.020 (3)00.006 (2)0
C40.0166 (19)0.018 (2)0.0175 (19)−0.0036 (15)0.0046 (15)−0.0055 (15)
C50.028 (3)0.010 (3)0.036 (3)00.014 (3)0
Geometric parameters (Å, º) top
Cd1—N1i2.306 (3)N2—H2A0.92
Cd1—N1ii2.306 (3)N2—H2B0.92
Cd1—N2iii2.364 (3)C2—C31.376 (4)
Cd1—N22.364 (3)C2—C41.391 (5)
Cd1—S1iii2.7143 (10)C3—C2iv1.376 (4)
Cd1—S12.7143 (10)C3—H30.95
S1—C11.643 (4)C4—C51.382 (4)
N1—C11.157 (4)C4—H40.95
N1—Cd1i2.306 (3)C5—C4iv1.382 (4)
N2—C21.439 (4)C5—H50.95
N1i—Cd1—N1ii90.81 (15)C2—N2—Cd1117.1 (2)
N1i—Cd1—N2iii96.91 (10)C2—N2—H2A108
N1ii—Cd1—N2iii83.89 (11)Cd1—N2—H2A108
N1i—Cd1—N283.89 (11)C2—N2—H2B108
N1ii—Cd1—N296.91 (10)Cd1—N2—H2B108
N2iii—Cd1—N2178.87 (14)H2A—N2—H2B107.3
N1i—Cd1—S1iii174.75 (8)C3—C2—C4120.2 (4)
N1ii—Cd1—S1iii92.41 (8)C3—C2—N2120.6 (3)
N2iii—Cd1—S1iii87.56 (8)C4—C2—N2119.1 (3)
N2—Cd1—S1iii91.60 (8)C2—C3—C2iv120.4 (5)
N1i—Cd1—S192.41 (8)C2—C3—H3119.8
N1ii—Cd1—S1174.75 (8)C2iv—C3—H3119.8
N2iii—Cd1—S191.60 (8)C5—C4—C2119.0 (4)
N2—Cd1—S187.56 (8)C5—C4—H4120.5
S1iii—Cd1—S184.68 (4)C2—C4—H4120.5
C1—S1—Cd199.92 (12)C4iv—C5—C4121.2 (5)
C1—N1—Cd1i165.4 (3)C4iv—C5—H5119.4
N1—C1—S1178.8 (3)C4—C5—H5119.4
N1i—Cd1—S1—C16.69 (14)S1iii—Cd1—N2—C281.6 (2)
N1ii—Cd1—S1—C1−121.1 (9)S1—Cd1—N2—C2166.2 (2)
N2iii—Cd1—S1—C1−90.29 (14)Cd1—N2—C2—C3−103.9 (3)
N2—Cd1—S1—C190.47 (15)Cd1—N2—C2—C472.5 (3)
S1iii—Cd1—S1—C1−177.70 (14)C4—C2—C3—C2iv0.0 (2)
Cd1i—N1—C1—S1122 (17)N2—C2—C3—C2iv176.3 (3)
Cd1—S1—C1—N1−147 (17)C3—C2—C4—C50.0 (4)
N1i—Cd1—N2—C2−101.1 (2)N2—C2—C4—C5−176.4 (3)
N1ii—Cd1—N2—C2−11.0 (3)C2—C4—C5—C4iv0.0 (2)
N2iii—Cd1—N2—C2123.9 (2)
Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, y, −z+1/2; (iv) −x+1, y, −z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···S1v0.922.673.589 (3)173
Symmetry code: (v) x, −y, z−1/2.
Selected bond lengths (Å) top
Cd1—N1i2.306 (3)Cd1—S12.7143 (10)
Cd1—N22.364 (3)
Symmetry code: (i) −x+3/2, −y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···S1ii0.922.673.589 (3)173.1
Symmetry code: (ii) x, −y, z−1/2.
 

Acknowledgements

The authors gratefully acknowledge the support of the Tunisian Ministry of Higher Education and Scientific Research.

References

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ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages m670-m671
doi:10.1107/S1600536813031255
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