(Acetato-κO)(acetato-κO,O′)bis­(1,3-diazinane-2-thione-κS)cadmium(II)

Mahmood, R.; Ghulam Hussain, S.; Fettouhi, M.; Isab, A.A.; Ahmad, S.

doi:10.1107/S1600536812041852

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1352-m1353

doi:10.1107/S1600536812041852

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(Acetato-κO)(acetato-κO,O′)bis(1,3-diazinane-2-thione-κS)cadmium(II)

Rashid Mahmood,^a Saima Ghulam Hussain,^b Mohammed Fettouhi,^c Anvarhusein A. Isab ^c and Saeed Ahmad ^b ^*

^aDivision of Science and Technology, University of Education, Township, Lahore, Pakistan, ^bDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan, and ^cDepartment of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia
^*Correspondence e-mail: saeed_a786@hotmail.com

(Received 29 August 2012; accepted 6 October 2012; online 13 October 2012)

In the title complex, [Cd(CH₃COO)₂(C₄H₈N₂S)₂], the Cd^II cation is coordinated by three acetate O atoms and two S atoms of Diaz [Diaz = 1,3-diazinane-2-thione = 3,4,5,6-tetrahydropyrimidine-2(1H)-thione]. The Cd^II coordination is augmented by one considerably longer Cd—O bond of 2.782 (3) Å to a carboxylate O atom. The resulting coordination polyhedron around the Cd^II cations can be described as a highly distorted octahedron. The Diaz ligand and the acetate anions are linked by N—H⋯O hydrogen-bonding interactions.

Related literature

For crystal structures of Cd^II complexes of thiones, see: Ahmad et al. (2011 , 2012 ); Altaf et al. (2011 ); Beheshti et al. (2007 ); Lobana et al. (2008 ); Nawaz et al. (2010); Moloto et al. (2003 , 2007 ); Wang et al. (2002 ); Wazeer et al. (2007 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

[Cd(C₂H₃O₂)₂(C₄H₈N₂S)₂]
M_r = 462.86
Triclinic, $[P \overline 1]$
a = 8.6930 (17) Å
b = 10.175 (2) Å
c = 12.203 (2) Å
α = 97.452 (4)°
β = 100.683 (4)°
γ = 111.610 (3)°
V = 962.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 294 K
0.19 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.781, T_max = 0.875
13173 measured reflections
4775 independent reflections
3705 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.082
S = 1.02
4775 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	1.94	2.779 (3)	167
N3—H3⋯O4	0.86	2.10	2.897 (4)	154
N2—H2⋯O2ⁱ	0.86	2.01	2.829 (3)	160
N4—H4⋯O1ⁱⁱ	0.86	2.03	2.836 (3)	156
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041852/nc2292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041852/nc2292Isup2.hkl

checkCIF report

Comment top

The structural reports on cadmium(II) complexes of thiones describe that in most of the cases, the cadmium(II) complexes exist as neutral monomeric (Ahmad et al. 2011, 2012; Beheshti et al., 2007; Lobana et al. 2008; Nawaz et al., 2010; Wazeer et al., 2007) or polymeric (Moloto et al., 2007; Wang et al., 2002) with cadmium atom possessing a tetrahedral or distorted octahedral coordination environment respectively. In continuation of our studies on the structural chemistry of cadmium(II) complexes with thione ligands, we report here the crystal structure of the title compound. The crystal structure of the title complex (Figure 1) consists of discrete monomeric species in which the Cd(II) ion is bound to two sulfur Diaz atoms, two oxygen atoms belonging to a chelating acetate and a third oxygen atom of a second acetate anion. The Cd—S bond distances are 2.5787 (8) and 2.529 (1) Å respectively while the Cd—O bond distances are in the range of 2.266 (2)- 2.421 (2) Å. In addition, a secondary bonding interaction takes place with the second oxygen of one acetate anion with a distance of 2.782 (3) Å. The van der Waals radii for cadmium and oxygen are 1.58 and 1.52 Å respectively (Bondi, 1964). Considering the secondary bonding, the geometry could be considered as highly distorted octahedral. The S—Cd—S bond angle is 97.02 (3) °, the O—Cd—O bond angle for the bidentate acetate ligand is 53.86 (7) ° and the S—Cd—O bond angles vary from 92.37 (5) ° to 144.34 (6) °. The Cd—S and Cd—O bond lengths are in agreement with those reported for related compounds. Two intramolecular (N—H···O) hydrogen bonds are found between the Diaz ligands and acetate anions. The discrte complex molecules are also linked by intermolecular N—H···O hydrogen bonding (Table 1).

Related literature top

For crystal structures of Cd^II complexes of thiones, see: Ahmad et al. (2011, 2012); Altaf et al. (2011); Beheshti et al. (2007); Lobana et al. (2008); Nawaz et al. (2010); Moloto et al. (2003, 2007); Wang et al. (2002); Wazeer et al. (2007). For van der Waals radii, see: Bondi (1964).

Experimental top

The title complex was prepared by adding 0.24 g (2.0 mmol) of 1,3-diazinane-2-thione in 15 ml of methanol to an aqueous solution (5 ml) of 0.26 g (1.0 mmol) cadmium sulfate in water followed by addition of 2 equivalents of sodium acetate in 10 ml water and stirring the mixture for 30 minutes. The colorless solution was filtered and the filtrate was kept at room temperature for crystallization. As a result, white crystalline product was obtained, that was washed with methanol and dried.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and dashed lines indicate intramolecular hydrogen bonding and the secondary Cd···O interaction.

(Acetato-κO)(acetato-κO,O')bis(1,3-diazinane-2-thione- κS)cadmium(II) top

Crystal data top

[Cd(C₂H₃O₂)₂(C₄H₈N₂S)₂]	Z = 2
M_r = 462.86	F(000) = 468
Triclinic, P1	D_x = 1.597 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6930 (17) Å	Cell parameters from 13173 reflections
b = 10.175 (2) Å	θ = 1.7–28.3°
c = 12.203 (2) Å	µ = 1.37 mm⁻¹
α = 97.452 (4)°	T = 294 K
β = 100.683 (4)°	Block, colourless
γ = 111.610 (3)°	0.19 × 0.18 × 0.10 mm
V = 962.6 (3) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	4775 independent reflections
Radiation source: normal-focus sealed tube	3705 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.781, T_max = 0.875	k = −13→13
13173 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0408P)² + 0.0579P] where P = (F_o² + 2F_c²)/3
4775 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Cd(C₂H₃O₂)₂(C₄H₈N₂S)₂]	γ = 111.610 (3)°
M_r = 462.86	V = 962.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.6930 (17) Å	Mo Kα radiation
b = 10.175 (2) Å	µ = 1.37 mm⁻¹
c = 12.203 (2) Å	T = 294 K
α = 97.452 (4)°	0.19 × 0.18 × 0.10 mm
β = 100.683 (4)°

Data collection top

Bruker SMART APEX area-detector diffractometer	4775 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3705 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.875	R_int = 0.024
13173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
4775 reflections	Δρ_min = −0.43 e Å⁻³
210 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

	x	y	z	U_iso*/U_eq
Cd1	0.71521 (3)	0.17566 (2)	0.769239 (17)	0.05732 (9)
S1	0.98165 (9)	0.11886 (8)	0.77361 (6)	0.05721 (17)
S2	0.73948 (12)	0.30728 (12)	0.60691 (8)	0.0827 (3)
O1	0.5230 (3)	−0.0768 (2)	0.69890 (17)	0.0679 (5)
O2	0.4199 (3)	0.0743 (2)	0.76067 (19)	0.0713 (6)
O3	0.7698 (3)	0.2558 (2)	0.96021 (19)	0.0753 (6)
O4	0.6916 (4)	0.4146 (3)	0.8923 (2)	0.1107 (10)
N1	1.0593 (3)	0.1951 (2)	1.00174 (18)	0.0515 (5)
H1	0.9615	0.2007	0.9917	0.062*
N2	1.2447 (3)	0.1265 (3)	0.92374 (19)	0.0569 (6)
H2	1.2731	0.0989	0.8638	0.068*
N3	0.4916 (3)	0.3743 (3)	0.6630 (2)	0.0655 (6)
H3	0.5640	0.4152	0.7283	0.079*
N4	0.4398 (3)	0.2662 (3)	0.4764 (2)	0.0677 (7)
H4	0.4757	0.2314	0.4233	0.081*
C1	1.1027 (3)	0.1503 (3)	0.9105 (2)	0.0464 (5)
C2	1.1658 (4)	0.2360 (3)	1.1187 (2)	0.0595 (7)
H2A	1.1236	0.1581	1.1579	0.071*
H2B	1.1597	0.3216	1.1596	0.071*
C3	1.3496 (4)	0.2664 (3)	1.1175 (3)	0.0623 (7)
H3A	1.4004	0.3573	1.0945	0.075*
H3B	1.4150	0.2745	1.1935	0.075*
C4	1.3539 (4)	0.1449 (3)	1.0350 (3)	0.0612 (7)
H4A	1.4702	0.1670	1.0292	0.073*
H4B	1.3143	0.0559	1.0624	0.073*
C5	0.5411 (4)	0.3152 (3)	0.5810 (2)	0.0593 (7)
C6	0.2707 (4)	0.2682 (4)	0.4463 (3)	0.0800 (10)
H6A	0.1956	0.1855	0.3854	0.096*
H6B	0.2784	0.3556	0.4196	0.096*
C7	0.2012 (5)	0.2632 (5)	0.5474 (3)	0.0978 (13)
H7A	0.1735	0.1679	0.5645	0.117*
H7B	0.0962	0.2783	0.5305	0.117*
C8	0.3232 (4)	0.3746 (4)	0.6498 (3)	0.0768 (9)
H8A	0.3282	0.4695	0.6413	0.092*
H8B	0.2835	0.3544	0.7174	0.092*
C9	0.4005 (3)	−0.0511 (3)	0.7195 (2)	0.0561 (6)
C10	0.2272 (4)	−0.1727 (4)	0.6978 (4)	0.0892 (11)
H10A	0.2125	−0.2038	0.7676	0.134*
H10B	0.2183	−0.2523	0.6416	0.134*
H10C	0.1401	−0.1395	0.6704	0.134*
C11	0.7493 (3)	0.3726 (3)	0.9725 (2)	0.0574 (7)
C12	0.7991 (5)	0.4611 (3)	1.0914 (3)	0.0779 (10)
H12A	0.9214	0.5038	1.1188	0.117*
H12B	0.7504	0.4001	1.1406	0.117*
H12C	0.7573	0.5363	1.0911	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.05297 (13)	0.06353 (14)	0.05545 (14)	0.02626 (10)	0.00898 (9)	0.01124 (9)
S1	0.0544 (4)	0.0699 (4)	0.0480 (4)	0.0297 (3)	0.0097 (3)	0.0057 (3)
S2	0.0714 (5)	0.1273 (8)	0.0748 (6)	0.0542 (6)	0.0299 (4)	0.0473 (5)
O1	0.0557 (11)	0.0753 (13)	0.0716 (13)	0.0327 (10)	0.0119 (10)	−0.0007 (10)
O2	0.0577 (12)	0.0688 (13)	0.0832 (15)	0.0238 (10)	0.0231 (11)	−0.0012 (11)
O3	0.0630 (13)	0.0762 (14)	0.0839 (15)	0.0388 (11)	0.0061 (11)	−0.0071 (11)
O4	0.164 (3)	0.0721 (16)	0.0651 (16)	0.0344 (17)	−0.0127 (16)	0.0102 (12)
N1	0.0450 (11)	0.0592 (13)	0.0509 (13)	0.0223 (10)	0.0126 (9)	0.0096 (10)
N2	0.0503 (13)	0.0674 (14)	0.0554 (13)	0.0291 (11)	0.0123 (10)	0.0068 (11)
N3	0.0695 (16)	0.0747 (16)	0.0498 (14)	0.0336 (13)	0.0068 (11)	0.0033 (12)
N4	0.0780 (17)	0.0855 (18)	0.0496 (14)	0.0462 (15)	0.0164 (12)	0.0077 (12)
C1	0.0436 (13)	0.0442 (13)	0.0503 (14)	0.0163 (11)	0.0129 (10)	0.0093 (11)
C2	0.0680 (18)	0.0619 (17)	0.0464 (15)	0.0261 (14)	0.0098 (13)	0.0115 (12)
C3	0.0562 (17)	0.0582 (16)	0.0622 (18)	0.0188 (13)	0.0008 (13)	0.0114 (13)
C4	0.0504 (15)	0.0641 (17)	0.0674 (18)	0.0255 (14)	0.0046 (13)	0.0162 (14)
C5	0.0674 (18)	0.0646 (17)	0.0522 (16)	0.0305 (15)	0.0159 (14)	0.0206 (13)
C6	0.078 (2)	0.100 (3)	0.0587 (19)	0.045 (2)	0.0041 (16)	−0.0017 (17)
C7	0.071 (2)	0.147 (4)	0.068 (2)	0.046 (2)	0.0096 (18)	0.000 (2)
C8	0.078 (2)	0.093 (2)	0.066 (2)	0.0462 (19)	0.0191 (16)	0.0012 (17)
C9	0.0519 (15)	0.0685 (18)	0.0475 (15)	0.0267 (14)	0.0096 (12)	0.0082 (13)
C10	0.066 (2)	0.077 (2)	0.110 (3)	0.0162 (18)	0.0223 (19)	0.004 (2)
C11	0.0501 (15)	0.0525 (16)	0.0573 (17)	0.0102 (12)	0.0139 (12)	0.0025 (13)
C12	0.093 (2)	0.0612 (19)	0.0603 (19)	0.0145 (17)	0.0210 (17)	−0.0023 (15)

Geometric parameters (Å, º) top

Cd1—O3	2.266 (2)	C2—C3	1.515 (4)
Cd1—O2	2.364 (2)	C2—H2A	0.9700
Cd1—O1	2.421 (2)	C2—H2B	0.9700
Cd1—S2	2.5291 (10)	C3—C4	1.507 (4)
Cd1—S1	2.5787 (8)	C3—H3A	0.9700
Cd1—O4	2.782 (3)	C3—H3B	0.9700
S1—C1	1.721 (3)	C4—H4A	0.9700
S2—C5	1.728 (3)	C4—H4B	0.9700
O1—C9	1.245 (3)	C6—C7	1.470 (5)
O2—C9	1.247 (3)	C6—H6A	0.9700
O3—C11	1.259 (4)	C6—H6B	0.9700
O4—C11	1.215 (4)	C7—C8	1.492 (5)
N1—C1	1.319 (3)	C7—H7A	0.9700
N1—C2	1.462 (3)	C7—H7B	0.9700
N1—H1	0.8600	C8—H8A	0.9700
N2—C1	1.329 (3)	C8—H8B	0.9700
N2—C4	1.451 (3)	C9—C10	1.505 (4)
N2—H2	0.8600	C10—H10A	0.9600
N3—C5	1.320 (4)	C10—H10B	0.9600
N3—C8	1.444 (4)	C10—H10C	0.9600
N3—H3	0.8600	C11—C12	1.499 (4)
N4—C5	1.322 (4)	C12—H12A	0.9600
N4—C6	1.456 (4)	C12—H12B	0.9600
N4—H4	0.8600	C12—H12C	0.9600

O3—Cd1—O2	89.05 (8)	H3A—C3—H3B	108.3
O3—Cd1—O1	114.48 (8)	N2—C4—C3	109.3 (2)
O2—Cd1—O1	53.86 (7)	N2—C4—H4A	109.8
O3—Cd1—S2	132.00 (7)	C3—C4—H4A	109.8
O2—Cd1—S2	105.07 (6)	N2—C4—H4B	109.8
O1—Cd1—S2	110.65 (6)	C3—C4—H4B	109.8
O3—Cd1—S1	96.66 (5)	H4A—C4—H4B	108.3
O2—Cd1—S1	144.34 (6)	N3—C5—N4	119.3 (3)
O1—Cd1—S1	92.37 (5)	N3—C5—S2	121.1 (2)
S2—Cd1—S1	97.02 (3)	N4—C5—S2	119.5 (2)
O3—Cd1—O4	49.63 (8)	N4—C6—C7	109.1 (3)
O2—Cd1—O4	81.01 (8)	N4—C6—H6A	109.9
O1—Cd1—O4	134.07 (8)	C7—C6—H6A	109.9
S2—Cd1—O4	86.90 (6)	N4—C6—H6B	109.9
S1—Cd1—O4	128.48 (7)	C7—C6—H6B	109.9
C1—S1—Cd1	112.35 (9)	H6A—C6—H6B	108.3
C5—S2—Cd1	98.79 (10)	C6—C7—C8	112.5 (3)
C9—O1—Cd1	91.30 (17)	C6—C7—H7A	109.1
C9—O2—Cd1	93.95 (17)	C8—C7—H7A	109.1
C11—O3—Cd1	105.62 (19)	C6—C7—H7B	109.1
C11—O4—Cd1	81.81 (19)	C8—C7—H7B	109.1
C1—N1—C2	124.6 (2)	H7A—C7—H7B	107.8
C1—N1—H1	117.7	N3—C8—C7	110.3 (3)
C2—N1—H1	117.7	N3—C8—H8A	109.6
C1—N2—C4	122.8 (2)	C7—C8—H8A	109.6
C1—N2—H2	118.6	N3—C8—H8B	109.6
C4—N2—H2	118.6	C7—C8—H8B	109.6
C5—N3—C8	124.0 (2)	H8A—C8—H8B	108.1
C5—N3—H3	118.0	O1—C9—O2	120.9 (3)
C8—N3—H3	118.0	O1—C9—C10	120.2 (3)
C5—N4—C6	123.5 (2)	O2—C9—C10	118.9 (3)
C5—N4—H4	118.3	C9—C10—H10A	109.5
C6—N4—H4	118.3	C9—C10—H10B	109.5
N1—C1—N2	119.2 (2)	H10A—C10—H10B	109.5
N1—C1—S1	122.82 (19)	C9—C10—H10C	109.5
N2—C1—S1	117.95 (19)	H10A—C10—H10C	109.5
N1—C2—C3	110.1 (2)	H10B—C10—H10C	109.5
N1—C2—H2A	109.6	O4—C11—O3	122.5 (3)
C3—C2—H2A	109.6	O4—C11—C12	119.9 (3)
N1—C2—H2B	109.6	O3—C11—C12	117.6 (3)
C3—C2—H2B	109.6	C11—C12—H12A	109.5
H2A—C2—H2B	108.2	C11—C12—H12B	109.5
C4—C3—C2	109.2 (2)	H12A—C12—H12B	109.5
C4—C3—H3A	109.8	C11—C12—H12C	109.5
C2—C3—H3A	109.8	H12A—C12—H12C	109.5
C4—C3—H3B	109.8	H12B—C12—H12C	109.5
C2—C3—H3B	109.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.94	2.779 (3)	167
N3—H3···O4	0.86	2.10	2.897 (4)	154
N2—H2···O2ⁱ	0.86	2.01	2.829 (3)	160
N4—H4···O1ⁱⁱ	0.86	2.03	2.836 (3)	156

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₂H₃O₂)₂(C₄H₈N₂S)₂]
M_r	462.86
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.6930 (17), 10.175 (2), 12.203 (2)
α, β, γ (°)	97.452 (4), 100.683 (4), 111.610 (3)
V (Å³)	962.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.37
Crystal size (mm)	0.19 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.781, 0.875
No. of measured, independent and observed [I > 2σ(I)] reflections	13173, 4775, 3705
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.082, 1.02
No. of reflections	4775
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.43

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.94	2.779 (3)	166.6
N3—H3···O4	0.86	2.10	2.897 (4)	153.5
N2—H2···O2ⁱ	0.86	2.01	2.829 (3)	160.0
N4—H4···O1ⁱⁱ	0.86	2.03	2.836 (3)	156.3

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Acknowledgements

The authors gratefully acknowledge King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, for providing X-ray facilities.

References

Ahmad, S., Altaf, M., Stoeckli-Evans, H., Isab, A. A., Malik, M. R., Ali, S. & Shuja, S. (2011). J. Chem. Crystallogr. 41, 1099–1104. Web of Science CSD CrossRef CAS Google Scholar
Ahmad, S., Amir, Q., Naz, G., Fettouhi, M., Isab, A. A., Rüffer, T. & Lang, H. (2012). J. Chem. Crystallogr. 42, 615–620. Web of Science CSD CrossRef CAS Google Scholar
Altaf, M., Stoeckli Evans, H., Murtaza, G., Isab, A. A., Ahmad, S. & Shaheen, M. A. (2011). J. Struct. Chem. 52, 625–630. CrossRef CAS Google Scholar
Beheshti, A., Clegg, W., Dale, S. H. & Hyvadi, R. (2007). Inorg. Chim. Acta, 360, 2967–2972. Web of Science CSD CrossRef CAS Google Scholar
Bondi, A. (1964). J. Phys. Chem. 68, 441–451. CrossRef CAS Web of Science Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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
Moloto, M. J., Malik, M. A., O'Brien, P., Motevalli, M. & Kolawole, G. A. (2003). Polyhedron, 22, 595–603. Web of Science CSD CrossRef CAS Google Scholar
Moloto, N., Revaprasadu, N., Moloto, M. J., O'Brien, P. & Helliwell, M. (2007). Polyhedron, 26, 3947–3955. Web of Science CSD CrossRef CAS 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
Sheldrick, G. M. (1996). 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
Wang, X. Q., Yu, W. T., Xu, D., Lu, M. K. & Yuan, D. R. (2002). Acta Cryst. C58, m336–m337. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wazeer, M. I. M., Isab, A. A. & Fettouhi, M. (2007). Polyhedron, 26, 1725–1730. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar