catena-Poly[[[aqua­(1,10-phenanthroline-κ2N,N′)zinc]-μ-acetyl­ene­dicarboxyl­ato-κ2O1:O2] monohydrate]

Fettouhi, M.

doi:10.1107/S1600536812025068

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m895

https://doi.org/10.1107/S1600536812025068

Open

access

catena-Poly[[[aqua(1,10-phenanthroline-κ²N,N′)zinc]-μ-acetylenedicarboxylato-κ²O¹:O²] monohydrate]

Mohammed Fettouhi ^a ^*

^aDepartment of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia
^*Correspondence e-mail: fettouhi@kfupm.edu.sa

(Received 24 May 2012; accepted 1 June 2012; online 13 June 2012)

In the title complex, {[Zn(C₄O₄)(C₁₂H₈N₂)(H₂O)]·H₂O}_n, the pentacoordinated Zn^II ion is bound to two N atoms of the 1,10-phenanthroline ligand, two O atoms from two bridging acetylenedicarboxylate anions and a water O atom in a distorted trigonal–bipyramidal geometry. The crystal structure is characterized by polymeric zigzag chains running parallel to [2-10] and is stabilized by O—H⋯O hydrogen bonds.

Related literature

For background to polymetallic complexes, see: Winpenny (2001 ); Swiegers & Malefetse (2000 ). For polymeric complexes based on acetylenedicarboxylate, see: Hermann et al. (2011 ); Lin et al. (2011 ); Zheng et al. (2010 ). For a related six-coordinate octahedral Zn^II–pyridine complex with similar hydrogen-bonding interactions, see: Stein & Ruschewitz (2009 ).

Experimental

Crystal data

[Zn(C₄O₄)(C₁₂H₈N₂)(H₂O)]·H₂O
M_r = 393.65
Triclinic, $[P \overline 1]$
a = 7.9592 (8) Å
b = 7.9598 (8) Å
c = 13.3712 (13) Å
α = 105.062 (2)°
β = 101.287 (2)°
γ = 99.131 (2)°
V = 782.30 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 296 K
0.37 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.588, T_max = 0.896
6649 measured reflections
3398 independent reflections
3069 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.111
S = 1.14
3398 reflections
242 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1W⋯O3ⁱ	0.83 (2)	1.91 (2)	2.741 (4)	176 (4)
O5—H2W⋯O6ⁱⁱ	0.83 (2)	1.93 (2)	2.746 (4)	167 (5)
O6—H3W⋯O2ⁱⁱⁱ	0.83 (2)	2.04 (3)	2.847 (5)	164 (6)
O6—H4W⋯O4^iv	0.85 (2)	1.97 (2)	2.806 (4)	168 (5)
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y+1, z; (iii) x, y-1, z; (iv) x+1, y, z.

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: https://doi.org/10.1107/S1600536812025068/bt5933sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025068/bt5933Isup2.hkl

checkCIF report

Comment top

The design and structural control of polymetallic complexes is an area of interest owing to wide potential applications (Winpenny, 2001; Swiegers et al., 2000). In this context, acetylenedicarboxylate is a particularly attracting ligand as a building block of polymeric metal complexes (Hermann et al., 2011; Lin et al., 2011; Zheng et al., 2010). I report herein on a polymeric zinc complex based on 1,10-phenanthroline and the acetylenedicarboxylate anion. The Zn(II) ion is bound to two nitrogen atoms of the 1,10-phenanthroline ligand, two oxygen atoms each belonging to an acetylenedicarboxylate anion and an oxygen atom of a water molecule (Figure 1). The geometry is distorted trigonal bipyramidal where the equatorial positions are occupied by the two carboxylate oxygen atoms and one nitrogen atom. The two acetylenedicarboxylate anions are each located on an inversion center and bridging Zn(II) ions to generate a zigzag chain structure parallel to [2 1 0] (Figure 2). The coordinated water molecule belonging to one chain interacts with a carbonyl oxygen of an adjacent chain, giving rise to eight-membered [Zn—(O···H—O)₂—Zn] inter-chain rings with a chair configuration. One crystallization water molecule in the lattice has hydrogen bonding interactions connecting three adjacent chains by interacting with two carbonyl oxygen atoms of the first and second chain respectively in addition to a hydrogen atom of the coordinated water molecule of the third chain. A six-coordinate octahedral pyridine complex with similar hydrogen bonding interactions has been reported (Stein et al., 2009).

Related literature top

For background to polymetallic complexes, see: Winpenny (2001); Swiegers & Malefetse (2000). For polymeric complexes based on acetylenedicarboxylate, see: Hermann et al. (2011); Lin et al. (2011); Zheng et al. (2010). For a related six-coordinate octahedral Zn^II–pyridine complex with similar hydrogen-bonding interactions, see: Stein & Ruschewitz (2009).

Experimental top

Acetylenedicarboxylic acid (0.2 mmol, 0.0228 g) and 1,10-phenanthroline (0.2 mmol, 0.0397 g) were mixed in 2 ml e thanol. A clear solution was obtained upon addition of an aqueous solution (2 ml) of Zn(NO₃)₂.6H₂O (0.2 mmol, 0.0595 g). The pH was then adjusted to 4.4 using NaOH (0.010 M) and the solution was filtered. Colorless crystals suitable for X-ray diffraction were obtained after few days by slow evaporation of the filtrate.

Structure description top

For background to polymetallic complexes, see: Winpenny (2001); Swiegers & Malefetse (2000). For polymeric complexes based on acetylenedicarboxylate, see: Hermann et al. (2011); Lin et al. (2011); Zheng et al. (2010). For a related six-coordinate octahedral Zn^II–pyridine complex with similar hydrogen-bonding interactions, see: Stein & Ruschewitz (2009).

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 a fragment of the title compound showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level (Symmetry codes: i = -x + 1,-y + 2,-z; ii = -x,-y,-z).
	Fig. 2. Packing diagram of the title complex showing the H-bonding interactions.

catena-Poly[[[aqua(1,10-phenanthroline-κ²N,N')zinc]- µ-acetylenedicarboxylato-κ²O¹:O²] monohydrate] top

Crystal data top

[Zn(C₄O₄)(C₁₂H₈N₂)(H₂O)]·H₂O	Z = 2
M_r = 393.65	F(000) = 400
Triclinic, P1	D_x = 1.671 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9592 (8) Å	Cell parameters from 6941 reflections
b = 7.9598 (8) Å	θ = 1.6–28.3°
c = 13.3712 (13) Å	µ = 1.61 mm⁻¹
α = 105.062 (2)°	T = 296 K
β = 101.287 (2)°	Parallelepiped, yellow
γ = 99.131 (2)°	0.37 × 0.14 × 0.07 mm
V = 782.30 (13) Å³

Data collection top

Bruker Smart Apex area detector diffractometer	3398 independent reflections
Radiation source: normal-focus sealed tube	3069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.1°, θ_min = 1.6°
Absorption correction: multi-scan SADABS; Sheldrick, 1996	h = −10→10
T_min = 0.588, T_max = 0.896	k = −10→10
6649 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0449P)² + 1.0051P] where P = (F_o² + 2F_c²)/3
3398 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.71 e Å⁻³
4 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Zn(C₄O₄)(C₁₂H₈N₂)(H₂O)]·H₂O	γ = 99.131 (2)°
M_r = 393.65	V = 782.30 (13) Å³
Triclinic, P1	Z = 2
a = 7.9592 (8) Å	Mo Kα radiation
b = 7.9598 (8) Å	µ = 1.61 mm⁻¹
c = 13.3712 (13) Å	T = 296 K
α = 105.062 (2)°	0.37 × 0.14 × 0.07 mm
β = 101.287 (2)°

Data collection top

Bruker Smart Apex area detector diffractometer	3398 independent reflections
Absorption correction: multi-scan SADABS; Sheldrick, 1996	3069 reflections with I > 2σ(I)
T_min = 0.588, T_max = 0.896	R_int = 0.018
6649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.71 e Å⁻³
3398 reflections	Δρ_min = −0.34 e Å⁻³
242 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
Zn1	0.23205 (5)	0.62227 (5)	0.17319 (3)	0.02899 (13)
N1	0.4701 (4)	0.5448 (4)	0.2254 (2)	0.0364 (6)
N2	0.2790 (4)	0.7239 (4)	0.3405 (2)	0.0339 (6)
O1	0.3084 (3)	0.7402 (4)	0.0701 (2)	0.0472 (7)
O2	0.5273 (5)	0.9248 (5)	0.1989 (2)	0.0753 (11)
O3	0.1288 (3)	0.3764 (3)	0.06832 (19)	0.0386 (5)
O4	0.0871 (4)	0.2719 (3)	0.2021 (2)	0.0481 (6)
O5	−0.0117 (4)	0.6855 (4)	0.1476 (2)	0.0440 (6)
O6	0.9009 (5)	−0.0096 (5)	0.2544 (3)	0.0570 (8)
C1	0.4810 (5)	0.9623 (5)	0.0304 (3)	0.0432 (8)
C2	0.4356 (5)	0.8714 (5)	0.1069 (3)	0.0417 (8)
C3	0.1800 (6)	0.8060 (5)	0.3967 (3)	0.0439 (8)
H3	0.0747	0.8234	0.3609	0.053*
C4	0.2293 (7)	0.8677 (6)	0.5091 (3)	0.0588 (12)
H4	0.1567	0.9244	0.5464	0.071*
C5	0.3816 (7)	0.8450 (6)	0.5629 (3)	0.0622 (13)
H5	0.4151	0.8868	0.6371	0.075*
C6	0.4893 (6)	0.7575 (5)	0.5058 (3)	0.0488 (10)
C7	0.6539 (7)	0.7268 (7)	0.5552 (4)	0.0673 (15)
H7	0.6943	0.7677	0.6293	0.081*
C8	0.7501 (6)	0.6408 (7)	0.4972 (4)	0.0674 (14)
H8	0.8569	0.6246	0.5319	0.081*
C9	0.6940 (5)	0.5727 (6)	0.3829 (4)	0.0519 (10)
C10	0.7835 (6)	0.4750 (6)	0.3164 (5)	0.0639 (13)
H10	0.8896	0.4513	0.3461	0.077*
C11	0.7161 (6)	0.4151 (6)	0.2092 (5)	0.0620 (12)
H11	0.7741	0.3486	0.1650	0.074*
C12	0.5598 (5)	0.4544 (5)	0.1665 (3)	0.0469 (9)
H12	0.5159	0.4152	0.0926	0.056*
C13	0.5344 (4)	0.6041 (5)	0.3325 (3)	0.0366 (7)
C14	0.4315 (5)	0.6990 (4)	0.3941 (3)	0.0366 (8)
C15	0.0839 (4)	0.2526 (4)	0.1076 (3)	0.0341 (7)
C16	0.0234 (5)	0.0720 (4)	0.0302 (3)	0.0356 (7)
H1W	−0.051 (5)	0.662 (6)	0.0818 (16)	0.045 (12)*
H2W	−0.029 (6)	0.775 (4)	0.188 (3)	0.066 (15)*
H3W	0.795 (3)	−0.030 (8)	0.226 (4)	0.079 (19)*
H4W	0.946 (6)	0.084 (4)	0.242 (4)	0.067 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0351 (2)	0.0266 (2)	0.02205 (19)	0.00242 (14)	0.00536 (14)	0.00573 (13)
N1	0.0358 (15)	0.0368 (15)	0.0382 (15)	0.0069 (12)	0.0095 (12)	0.0146 (12)
N2	0.0412 (15)	0.0308 (14)	0.0261 (13)	0.0017 (12)	0.0073 (11)	0.0071 (11)
O1	0.0449 (15)	0.0527 (16)	0.0448 (15)	−0.0046 (12)	0.0066 (12)	0.0288 (13)
O2	0.108 (3)	0.063 (2)	0.0341 (16)	−0.0223 (19)	0.0131 (16)	0.0070 (14)
O3	0.0461 (14)	0.0252 (11)	0.0342 (12)	−0.0001 (10)	−0.0009 (10)	0.0041 (9)
O4	0.0627 (17)	0.0410 (14)	0.0359 (14)	0.0072 (12)	0.0133 (12)	0.0057 (11)
O5	0.0486 (15)	0.0492 (16)	0.0330 (14)	0.0156 (12)	0.0073 (12)	0.0096 (12)
O6	0.068 (2)	0.057 (2)	0.0536 (18)	0.0196 (17)	0.0231 (17)	0.0201 (15)
C1	0.048 (2)	0.0378 (19)	0.040 (2)	−0.0027 (16)	0.0129 (16)	0.0109 (15)
C2	0.057 (2)	0.0356 (19)	0.0361 (19)	0.0063 (16)	0.0198 (17)	0.0130 (15)
C3	0.057 (2)	0.0379 (19)	0.0354 (19)	0.0064 (16)	0.0171 (17)	0.0071 (15)
C4	0.089 (3)	0.050 (2)	0.037 (2)	0.007 (2)	0.029 (2)	0.0050 (18)
C5	0.104 (4)	0.046 (2)	0.0228 (18)	−0.006 (2)	0.006 (2)	0.0065 (16)
C6	0.068 (3)	0.0359 (19)	0.0285 (18)	−0.0112 (18)	−0.0038 (17)	0.0108 (15)
C7	0.081 (3)	0.056 (3)	0.042 (2)	−0.015 (2)	−0.022 (2)	0.021 (2)
C8	0.053 (3)	0.066 (3)	0.068 (3)	−0.003 (2)	−0.022 (2)	0.032 (3)
C9	0.037 (2)	0.049 (2)	0.066 (3)	−0.0021 (17)	−0.0050 (18)	0.031 (2)
C10	0.037 (2)	0.061 (3)	0.100 (4)	0.015 (2)	0.006 (2)	0.040 (3)
C11	0.046 (2)	0.060 (3)	0.091 (4)	0.021 (2)	0.026 (2)	0.030 (3)
C12	0.048 (2)	0.049 (2)	0.049 (2)	0.0166 (18)	0.0177 (18)	0.0167 (18)
C13	0.0350 (17)	0.0340 (17)	0.0381 (18)	−0.0008 (14)	0.0018 (14)	0.0166 (14)
C14	0.0439 (19)	0.0299 (16)	0.0289 (16)	−0.0066 (14)	0.0013 (14)	0.0115 (13)
C15	0.0310 (16)	0.0267 (16)	0.0371 (18)	0.0055 (13)	0.0023 (13)	0.0017 (13)
C16	0.0385 (18)	0.0290 (15)	0.0378 (18)	0.0061 (13)	0.0084 (14)	0.0091 (13)

Geometric parameters (Å, º) top

Zn1—O1	1.992 (2)	C4—C5	1.347 (7)
Zn1—O3	2.021 (2)	C4—H4	0.9300
Zn1—O5	2.067 (3)	C5—C6	1.404 (7)
Zn1—N2	2.106 (3)	C5—H5	0.9300
Zn1—N1	2.129 (3)	C6—C14	1.400 (5)
N1—C12	1.318 (5)	C6—C7	1.435 (7)
N1—C13	1.349 (4)	C7—C8	1.335 (8)
N2—C3	1.324 (5)	C7—H7	0.9300
N2—C14	1.354 (4)	C8—C9	1.433 (7)
O1—C2	1.249 (4)	C8—H8	0.9300
O2—C2	1.227 (5)	C9—C10	1.403 (7)
O3—C15	1.267 (4)	C9—C13	1.408 (5)
O4—C15	1.227 (4)	C10—C11	1.353 (7)
O5—H1W	0.834 (19)	C10—H10	0.9300
O5—H2W	0.829 (19)	C11—C12	1.382 (6)
O6—H3W	0.826 (19)	C11—H11	0.9300
O6—H4W	0.849 (19)	C12—H12	0.9300
C1—C1ⁱ	1.185 (7)	C13—C14	1.435 (5)
C1—C2	1.465 (5)	C15—C16	1.477 (4)
C3—C4	1.406 (5)	C16—C16ⁱⁱ	1.171 (7)
C3—H3	0.9300

O1—Zn1—O3	97.23 (11)	C4—C5—H5	120.3
O1—Zn1—O5	92.99 (11)	C6—C5—H5	120.3
O3—Zn1—O5	90.36 (11)	C14—C6—C5	117.3 (4)
O1—Zn1—N2	129.20 (11)	C14—C6—C7	118.9 (4)
O3—Zn1—N2	133.15 (10)	C5—C6—C7	123.8 (4)
O5—Zn1—N2	92.75 (11)	C8—C7—C6	121.4 (4)
O1—Zn1—N1	97.80 (11)	C8—C7—H7	119.3
O3—Zn1—N1	90.77 (11)	C6—C7—H7	119.3
O5—Zn1—N1	168.92 (11)	C7—C8—C9	122.0 (4)
N2—Zn1—N1	78.48 (11)	C7—C8—H8	119.0
C12—N1—C13	118.7 (3)	C9—C8—H8	119.0
C12—N1—Zn1	128.1 (3)	C10—C9—C13	116.8 (4)
C13—N1—Zn1	113.2 (2)	C10—C9—C8	125.6 (4)
C3—N2—C14	118.2 (3)	C13—C9—C8	117.6 (4)
C3—N2—Zn1	128.4 (3)	C11—C10—C9	120.3 (4)
C14—N2—Zn1	113.4 (2)	C11—C10—H10	119.9
C2—O1—Zn1	117.2 (2)	C9—C10—H10	119.9
C15—O3—Zn1	116.4 (2)	C10—C11—C12	119.0 (4)
Zn1—O5—H1W	108 (3)	C10—C11—H11	120.5
Zn1—O5—H2W	120 (4)	C12—C11—H11	120.5
H1W—O5—H2W	119 (5)	N1—C12—C11	123.1 (4)
H3W—O6—H4W	105 (5)	N1—C12—H12	118.4
C1ⁱ—C1—C2	179.1 (5)	C11—C12—H12	118.4
O2—C2—O1	125.8 (3)	N1—C13—C9	122.1 (4)
O2—C2—C1	118.4 (3)	N1—C13—C14	117.1 (3)
O1—C2—C1	115.8 (3)	C9—C13—C14	120.8 (4)
N2—C3—C4	121.9 (4)	N2—C14—C6	123.0 (4)
N2—C3—H3	119.0	N2—C14—C13	117.8 (3)
C4—C3—H3	119.0	C6—C14—C13	119.3 (3)
C5—C4—C3	120.1 (4)	O4—C15—O3	125.6 (3)
C5—C4—H4	119.9	O4—C15—C16	119.3 (3)
C3—C4—H4	119.9	O3—C15—C16	115.2 (3)
C4—C5—C6	119.4 (4)	C16ⁱⁱ—C16—C15	179.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O3ⁱⁱⁱ	0.83 (2)	1.91 (2)	2.741 (4)	176 (4)
O5—H2W···O6^iv	0.83 (2)	1.93 (2)	2.746 (4)	167 (5)
O6—H3W···O2^v	0.83 (2)	2.04 (3)	2.847 (5)	164 (6)
O6—H4W···O4^vi	0.85 (2)	1.97 (2)	2.806 (4)	168 (5)

Symmetry codes: (iii) −x, −y+1, −z; (iv) x−1, y+1, z; (v) x, y−1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₄O₄)(C₁₂H₈N₂)(H₂O)]·H₂O
M_r	393.65
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9592 (8), 7.9598 (8), 13.3712 (13)
α, β, γ (°)	105.062 (2), 101.287 (2), 99.131 (2)
V (Å³)	782.30 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.37 × 0.14 × 0.07

Data collection
Diffractometer	Bruker Smart Apex area detector
Absorption correction	Multi-scan SADABS; Sheldrick, 1996
T_min, T_max	0.588, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	6649, 3398, 3069
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.14
No. of reflections	3398
No. of parameters	242
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.34

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
O5—H1W···O3ⁱ	0.834 (19)	1.91 (2)	2.741 (4)	176 (4)
O5—H2W···O6ⁱⁱ	0.829 (19)	1.93 (2)	2.746 (4)	167 (5)
O6—H3W···O2ⁱⁱⁱ	0.826 (19)	2.04 (3)	2.847 (5)	164 (6)
O6—H4W···O4^iv	0.849 (19)	1.97 (2)	2.806 (4)	168 (5)

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

Acknowledgements

We gratefully acknowledge King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia for financial support.

References

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
Hermann, D., Näther, C. & Ruschewitz, U. (2011). Solid State Sci. 13, 1096–1101. Web of Science CSD CrossRef CAS Google Scholar
Lin, J.-L., Zhu, H.-L., Zhang, J., Zhao, J.-M. & Zheng, Y.-Q. (2011). J. Mol. Struct. 995, 91–96. Web of Science CSD CrossRef CAS 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
Stein, I. & Ruschewitz, U. (2009). Z. Naturforsch. Teil B, 64, 1093–1097. CAS Google Scholar
Swiegers, G. F. & Malefetse, T. J. (2000). Chem. Rev. 100, 3483–3537. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Winpenny, R. E. P. (2001). Adv. Inorg. Chem. 52, 1–111. Web of Science CrossRef CAS Google Scholar
Zheng, Y.-Q., Zhang, J. & Liu, J.-Y. (2010). CrystEngComm, 12, 2740–2748. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.