catena-Poly[ammonium (cadmium-tri-μ-thio­cyanato-κ4S:N;κ2N:S)–1,4,10,13,16-hexa­oxa­cyclo­octa­decane (1/1)]

Ramesh, V.; Rajarajan, K.; Kumar, K.S.; Subashini, A.; NizamMohideen, M.

doi:10.1107/S1600536812004898

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m335-m336

doi:10.1107/S1600536812004898

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catena-Poly[ammonium (cadmium-tri-μ-thiocyanato-κ⁴S:N;κ²N:S)–1,4,10,13,16-hexaoxacyclooctadecane (1/1)]

V. Ramesh,^a K. Rajarajan,^b K. Sendil Kumar,^a A. Subashini ^a and M. NizamMohideen ^c ^*

^aResearch and Development Centre, Bharathiyar University, Coimbatore 641 046, India, ^bDepartment of Physics, Rajeswari Vedachalam Government Arts College, Chengalpet 603 001, India, and ^cDepartment of Physics, The New College (Autonomous), Chennai 600 014, India
^*Correspondence e-mail: mnizam_new@yahoo.in

(Received 20 September 2011; accepted 4 February 2012; online 24 February 2012)

In the title compound, {(NH₄)[Cd(NCS)₃]·C₁₂H₂₄O₆}_n, the Cd²⁺ ion, the ammonium cation, one of the SCN⁻ ligands and the macrocycle are located on mirror planes. The thiocyanate anions act as bridging ligands between the Cd^II ions, leading to a polymeric chain arrangement extending along [001] around a twofold screw axis. The ammonium ions are contained within the bowl of the macrocycle via extensive N—H⋯O hydrogen bonding.

Related literature

For a singly bridged cadmium thiocyanate complex, see: Bose et al. (2004 ). For a triply bridged cadmium thiocyanate complex, see: Chen et al. (2002 ). For an S-bound terminal thiocyanate cadmium complex, see: Nfor et al. (2006 ). For polymeric structures of complexes, see: Lobana et al. (2008 ). For the structures and properties of cadmium compounds, see: Gu et al. (2011 ); Zheng et al. (2004 ); Rajesh et al. (2004 ). For bond lengths and angles of related compounds, see: Nawaz et al. (2010 ).

Experimental

Crystal data

(NH₄)[Cd(NCS)₃]·C₁₂H₂₄O₆
M_r = 568.99
Orthorhombic, C m c 2₁
a = 14.7568 (6) Å
b = 15.4378 (6) Å
c = 10.6383 (5) Å
V = 2423.54 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.716, T_max = 0.796
11323 measured reflections
2483 independent reflections
2445 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.013
wR(F²) = 0.034
S = 1.09
2483 reflections
154 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 7607 Friedel pairs
Flack parameter: 0.005 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3E⋯O2	0.89 (1)	2.03 (1)	2.9130 (19)	174 (3)
N3—H3D⋯O4	0.90 (1)	2.05 (3)	2.892 (3)	155 (5)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004898/zb2021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004898/zb2021Isup2.hkl

checkCIF report

Comment top

Thiocyanate anion is known to bind the cadmium ion in different modes: terminal N-bound, terminal S-bound (Nfor et al. 2006) or N:S-bridging ligand. As a bridging ligand, it may give rise to a singly bridged (Bose et al. 2004), doubly bridged or triply bridged (Chen et al. 2002) cadmium complex. Cadmium(II) complexes with thiones possess a variety of structures ranging from four- to six-coordinate species with tetrahedral and octahedral environments for the CdII atom, respectively. In some cases, these units further aggregate to form polymeric structures (Lobana et al., 2008). The interest in cadmium compounds was provoked by their luminescent properties (Zheng et al., 2004), magnetic and catalytic properties (Gu et al., 2011) and non-linear optical properties (Rajesh et al., 2004). Herein, we report the synthesis and crystal structure of cadmium complex, the title compound, (I), coordinated by nitrogen and sulfur.

A perspective view of compound (I) with the atom-numbering scheme is shown in Fig. 1. The Cd^II ions are bridged by a pair of thiocyanate N:S-bridging ligands around a twofold screw axis. Two trans-N:S-bridging thiocyanates complete the N3S3 donor set around the Cd atom. The thiocyanate anions function as bridging ligands between the Cd^II centres, leading to a chain-like arrangement expanding along [001]. The thiocyanate ligands are almost linear.

The Cd—S bond lengths are 2.747 (4) and 2.728 (4) Å. These are in agreement with those reported for related compounds (Nawaz et al., 2010). The bond distances of N-bonded NCS groups [Cd—N(NCS) 2.347 (4) and 2.375 (4) Å]. These values agree well with those observed in [Cd(NCS)₂(1-vinylimidazole)₄] (Gu et al., 2011). The values of the bond angles around cadmium are close to those expected for a regular octahedral geometry, the largest angular deviation being observed for the N2 –Cd1- N1 angle [93.34 (5)°].

The parameters of hydrogen bonds are given in the Table 1. The thiocyanate anions function as bridging ligands between the CdII centres, leading to a chain-like arrangement are parallel to one another and expanding along [001]. The ammonium molecules also participate in extensive N—H···O hydrogen bonding, as shown in Fig. 2.

Related literature top

For a singly bridged cadmium thiocyanate complex, see: Bose et al. (2004). For a triply bridged cadmium thiocyanate complex, see: Chen et al. (2002). For an S-bound terminal thiocyanate cadmium complex, see: Nfor et al. (2006). For polymeric structures of complexes, see: Lobana et al. (2008). For the structures and properties of cadmium compounds, see: Gu et al. (2011); Zheng et al. (2004); Rajesh et al. (2004). For bond distances and angles, see: Nawaz et al. (2010).

Experimental top

The mixture of 18-crown-6 (C₁₂H₂₄O₆), CdCl₂ and NH₄SCN (molar ratio 1:1:3) were thoroughly dissolved in double distilled water and stirred for 5 h to obtain a homogeneous mixture. The colorless single crystals were obtained after the filtrate had been allowed to stand at room temperature for three weeks.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and publCIF (Westrip, 2010)..

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme and 50% probability displacement ellipsoids. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Molecular packing, viewed down c axis.

catena-Poly[ammonium (cadmium-tri-µ-thiocyanato-κ⁴S:N;κ²N:S)– 1,4,10,13,16-hexaoxacyclooctadecane (1/1)] top

Crystal data top

(NH₄)[Cd(NCS)₃]·C₁₂H₂₄O₆	F(000) = 1160
M_r = 568.99	D_x = 1.559 Mg m⁻³
Orthorhombic, Cmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 5280 reflections
a = 14.7568 (6) Å	θ = 2.6–26.7°
b = 15.4378 (6) Å	µ = 1.20 mm⁻¹
c = 10.6383 (5) Å	T = 293 K
V = 2423.54 (18) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2483 independent reflections
Radiation source: fine-focus sealed tube	2445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω and ϕ scan	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −18→18
T_min = 0.716, T_max = 0.796	k = −19→19
11323 measured reflections	l = −13→13

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.013	w = 1/[σ²(F_o²) + (0.020P)² + 0.1189P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.034	(Δ/σ)_max = 0.003
S = 1.09	Δρ_max = 0.20 e Å⁻³
2483 reflections	Δρ_min = −0.36 e Å⁻³
154 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.0058 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 7607 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.005 (15)

Crystal data top

(NH₄)[Cd(NCS)₃]·C₁₂H₂₄O₆	V = 2423.54 (18) Å³
M_r = 568.99	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 14.7568 (6) Å	µ = 1.20 mm⁻¹
b = 15.4378 (6) Å	T = 293 K
c = 10.6383 (5) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2483 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2445 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.796	R_int = 0.019
11323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.013	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.034	Δρ_max = 0.20 e Å⁻³
S = 1.09	Δρ_min = −0.36 e Å⁻³
2483 reflections	Absolute structure: Flack (1983), 7607 Friedel pairs
154 parameters	Absolute structure parameter: 0.005 (15)
5 restraints

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.

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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.61632 (10)	1.06679 (10)	0.72484 (14)	0.0337 (3)
C2	0.5000	0.87710 (13)	0.7689 (2)	0.0339 (4)
C3	0.9203 (2)	0.92459 (19)	1.0905 (3)	0.0905 (9)
H3A	0.9205	0.9648	1.1606	0.109*
H3B	0.9177	0.8662	1.1240	0.109*
C4	0.83962 (17)	0.94095 (17)	1.0097 (4)	0.0885 (10)
H4A	0.7851	0.9382	1.0604	0.106*
H4B	0.8436	0.9985	0.9736	0.106*
C5	0.76317 (15)	0.89705 (16)	0.8297 (3)	0.0811 (8)
H5A	0.7709	0.9545	0.7945	0.097*
H5B	0.7062	0.8959	0.8751	0.097*
C6	0.76078 (16)	0.83248 (19)	0.7272 (3)	0.0845 (9)
H6A	0.7596	0.7745	0.7621	0.101*
H6B	0.7065	0.8405	0.6770	0.101*
C7	0.8399 (2)	0.78484 (18)	0.5498 (3)	0.0923 (10)
H7A	0.7847	0.7908	0.5010	0.111*
H7B	0.8430	0.7259	0.5811	0.111*
C8	0.9199 (2)	0.80317 (17)	0.4690 (2)	0.0921 (10)
H8A	0.9185	0.7664	0.3952	0.110*
H8B	0.9186	0.8631	0.4415	0.110*
N1	0.60575 (11)	1.03455 (9)	0.62874 (16)	0.0496 (4)
N2	0.5000	0.91401 (12)	0.86273 (19)	0.0454 (5)
O1	1.0000	0.93509 (16)	1.0190 (3)	0.0776 (8)
O2	0.83461 (10)	0.87912 (10)	0.91271 (18)	0.0692 (4)
O3	0.83851 (11)	0.84297 (10)	0.65100 (18)	0.0703 (4)
O4	1.0000	0.78737 (15)	0.5382 (2)	0.0742 (7)
N3	1.0000	0.80499 (15)	0.8089 (2)	0.0476 (5)
Cd1	0.5000	0.971763 (8)	0.494929 (17)	0.03587 (6)
S1	0.63319 (3)	1.11267 (3)	0.86256 (4)	0.04216 (10)
S2	0.5000	0.82400 (4)	0.63561 (5)	0.04418 (14)
H3E	0.9497 (12)	0.8303 (18)	0.836 (3)	0.096 (10)*
H3C	1.0000	0.7522 (12)	0.844 (3)	0.076 (11)*
H3D	1.0000	0.817 (4)	0.7264 (16)	0.13 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0298 (7)	0.0389 (8)	0.0324 (7)	−0.0048 (6)	0.0026 (5)	0.0036 (6)
C2	0.0389 (11)	0.0289 (9)	0.0339 (12)	0.000	0.000	0.0067 (9)
C3	0.094 (2)	0.0801 (18)	0.097 (2)	0.0021 (14)	0.0308 (17)	−0.0239 (16)
C4	0.0702 (14)	0.0716 (13)	0.124 (3)	0.0100 (11)	0.035 (2)	−0.025 (2)
C5	0.0397 (11)	0.0731 (14)	0.130 (3)	0.0164 (10)	0.0147 (13)	0.0227 (16)
C6	0.0411 (11)	0.0820 (16)	0.130 (3)	−0.0007 (11)	−0.0205 (13)	0.0190 (17)
C7	0.097 (2)	0.0739 (16)	0.106 (2)	0.0214 (15)	−0.0549 (19)	−0.0204 (15)
C8	0.149 (3)	0.0678 (14)	0.0592 (19)	0.0343 (17)	−0.0297 (17)	−0.0138 (11)
N1	0.0539 (9)	0.0612 (9)	0.0337 (8)	−0.0148 (6)	0.0025 (7)	−0.0026 (7)
N2	0.0682 (13)	0.0370 (9)	0.0309 (9)	0.000	0.000	0.0015 (9)
O1	0.0683 (13)	0.0780 (14)	0.086 (2)	0.000	0.000	−0.0160 (14)
O2	0.0498 (8)	0.0570 (8)	0.1009 (13)	0.0127 (6)	0.0144 (8)	0.0011 (8)
O3	0.0628 (9)	0.0609 (8)	0.0872 (12)	0.0032 (7)	−0.0184 (8)	0.0017 (8)
O4	0.0963 (18)	0.0630 (13)	0.0632 (14)	0.000	0.000	−0.0012 (10)
N3	0.0385 (12)	0.0456 (12)	0.0587 (15)	0.000	0.000	0.0006 (10)
Cd1	0.04531 (9)	0.03708 (8)	0.02522 (8)	0.000	0.000	−0.00054 (7)
S1	0.0465 (2)	0.0454 (2)	0.0346 (2)	−0.00946 (16)	0.00023 (17)	−0.00481 (17)
S2	0.0649 (4)	0.0355 (3)	0.0322 (3)	0.000	0.000	−0.0024 (2)

Geometric parameters (Å, º) top

C1—N1	1.148 (2)	C7—C8	1.488 (4)
C1—S1	1.6463 (15)	C7—H7A	0.9700
C2—N2	1.149 (3)	C7—H7B	0.9700
C2—S2	1.638 (2)	C8—O4	1.413 (3)
C3—O1	1.410 (3)	C8—H8A	0.9700
C3—C4	1.490 (5)	C8—H8B	0.9700
C3—H3A	0.9700	N1—Cd1	2.3241 (16)
C3—H3B	0.9700	N2—Cd1ⁱ	2.256 (2)
C4—O2	1.408 (4)	O1—C3ⁱⁱ	1.410 (3)
C4—H4A	0.9700	O4—C8ⁱⁱ	1.413 (3)
C4—H4B	0.9700	N3—H3E	0.888 (10)
C5—O2	1.403 (3)	N3—H3C	0.897 (10)
C5—C6	1.478 (4)	N3—H3D	0.898 (10)
C5—H5A	0.9700	Cd1—N2ⁱⁱⁱ	2.256 (2)
C5—H5B	0.9700	Cd1—N1^iv	2.3241 (16)
C6—O3	1.414 (3)	Cd1—S2	2.7283 (6)
C6—H6A	0.9700	Cd1—S1ⁱⁱⁱ	2.7468 (4)
C6—H6B	0.9700	Cd1—S1^v	2.7468 (4)
C7—O3	1.402 (3)	S1—Cd1ⁱ	2.7468 (4)

N1—C1—S1	179.10 (16)	O4—C8—C7	109.28 (19)
N2—C2—S2	179.69 (19)	O4—C8—H8A	109.8
O1—C3—C4	109.6 (3)	C7—C8—H8A	109.8
O1—C3—H3A	109.7	O4—C8—H8B	109.8
C4—C3—H3A	109.7	C7—C8—H8B	109.8
O1—C3—H3B	109.7	H8A—C8—H8B	108.3
C4—C3—H3B	109.7	C1—N1—Cd1	144.86 (14)
H3A—C3—H3B	108.2	C2—N2—Cd1ⁱ	158.30 (17)
O2—C4—C3	110.48 (19)	C3ⁱⁱ—O1—C3	113.1 (4)
O2—C4—H4A	109.6	C5—O2—C4	111.54 (19)
C3—C4—H4A	109.6	C7—O3—C6	112.2 (2)
O2—C4—H4B	109.6	C8—O4—C8ⁱⁱ	113.4 (3)
C3—C4—H4B	109.6	H3E—N3—H3C	105 (2)
H4A—C4—H4B	108.1	H3E—N3—H3D	103 (3)
O2—C5—C6	110.46 (18)	H3C—N3—H3D	127 (5)
O2—C5—H5A	109.6	N2ⁱⁱⁱ—Cd1—N1	93.20 (5)
C6—C5—H5A	109.6	N2ⁱⁱⁱ—Cd1—N1^iv	93.20 (5)
O2—C5—H5B	109.6	N1—Cd1—N1^iv	84.36 (8)
C6—C5—H5B	109.6	N2ⁱⁱⁱ—Cd1—S2	174.69 (5)
H5A—C5—H5B	108.1	N1—Cd1—S2	90.73 (4)
O3—C6—C5	109.0 (2)	N1^iv—Cd1—S2	90.73 (4)
O3—C6—H6A	109.9	N2ⁱⁱⁱ—Cd1—S1ⁱⁱⁱ	92.94 (4)
C5—C6—H6A	109.9	N1—Cd1—S1ⁱⁱⁱ	172.93 (4)
O3—C6—H6B	109.9	N1^iv—Cd1—S1ⁱⁱⁱ	91.80 (4)
C5—C6—H6B	109.9	S2—Cd1—S1ⁱⁱⁱ	83.363 (12)
H6A—C6—H6B	108.3	N2ⁱⁱⁱ—Cd1—S1^v	92.94 (4)
O3—C7—C8	109.5 (2)	N1—Cd1—S1^v	91.80 (4)
O3—C7—H7A	109.8	N1^iv—Cd1—S1^v	172.93 (4)
C8—C7—H7A	109.8	S2—Cd1—S1^v	83.363 (12)
O3—C7—H7B	109.8	S1ⁱⁱⁱ—Cd1—S1^v	91.373 (19)
C8—C7—H7B	109.8	C1—S1—Cd1ⁱ	98.27 (5)
H7A—C7—H7B	108.2	C2—S2—Cd1	93.24 (7)

O1—C3—C4—O2	63.7 (3)	C1—N1—Cd1—N2ⁱⁱⁱ	107.3 (2)
O2—C5—C6—O3	−67.4 (2)	C1—N1—Cd1—N1^iv	14.4 (2)
O3—C7—C8—O4	64.2 (3)	C1—N1—Cd1—S2	−76.3 (2)
C4—C3—O1—C3ⁱⁱ	177.23 (15)	C1—N1—Cd1—S1^v	−159.7 (2)
C6—C5—O2—C4	178.6 (2)	N1—Cd1—S2—C2	42.19 (4)
C3—C4—O2—C5	−175.5 (2)	N1^iv—Cd1—S2—C2	−42.19 (4)
C8—C7—O3—C6	176.27 (19)	S1ⁱⁱⁱ—Cd1—S2—C2	−133.916 (9)
C5—C6—O3—C7	−178.75 (19)	S1^v—Cd1—S2—C2	133.916 (9)
C7—C8—O4—C8ⁱⁱ	−179.93 (16)

Symmetry codes: (i) −x+1, −y+2, z+1/2; (ii) −x+2, y, z; (iii) −x+1, −y+2, z−1/2; (iv) −x+1, y, z; (v) x, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3E···O2	0.89 (1)	2.03 (1)	2.9130 (19)	174 (3)
N3—H3D···O4	0.90 (1)	2.05 (3)	2.892 (3)	155 (5)

Experimental details

Crystal data
Chemical formula	(NH₄)[Cd(NCS)₃]·C₁₂H₂₄O₆
M_r	568.99
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	293
a, b, c (Å)	14.7568 (6), 15.4378 (6), 10.6383 (5)
V (Å³)	2423.54 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.716, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	11323, 2483, 2445
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.013, 0.034, 1.09
No. of reflections	2483
No. of parameters	154
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)	0.20, −0.36
Absolute structure	Flack (1983), 7607 Friedel pairs
Absolute structure parameter	0.005 (15)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and publCIF (Westrip, 2010)..

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3E···O2	0.888 (10)	2.029 (10)	2.9130 (19)	174 (3)
N3—H3D···O4	0.898 (10)	2.05 (3)	2.892 (3)	155 (5)

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help in collecting the X-ray intensity data.

References

Bose, D., Banerjee, J., Rahaman, S. H., Mostafa, G., Fun, H.-K., Walsh, R. D. B., Zaworotko, M. J. & Ghosh, B. K. (2004). Polyhedron, 23, 2045–2053. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, W., Liu, F. & You, X. (2002). J. Solid State Chem. 167, 119–125. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gu, J. Z., Lv, D. Y., Gao, Z. Q., Liu, J. Z., Dou, W. & Tang, Y. (2011). J. Solid State Chem. 184, 675–683. Web of Science CSD CrossRef CAS Google Scholar
Lobana, T. S., Sharma, R., Sharma, R., Sultana, R. & Butcher, R. J. (2008). Z. Anorg. Allg. Chem. 634, 718–723. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nawaz, S., Sadaf, S., Fettouhi, M., Fazal, A. & Ahmad, S. (2010). Acta Cryst. E66, m950. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nfor, E. N., Liu, W., Zuo, J.-L. & You, X.-Z. (2006). Transition Met. Chem. 31, 837–841. Web of Science CSD CrossRef CAS Google Scholar
Rajesh, N. P., Kannan, V., Ashok, M., Sivaji, K., Raghavan, P. S. & Ramasamy, P. (2004). J. Cryst. Growth, 262, 561–566. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, S.-L., Yang, J.-H., Yu, X.-L., Chen, X.-M. & Wong, W.-T. (2004). Inorg. Chem. 43, 830–838. Web of Science CSD CrossRef PubMed CAS Google Scholar

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