Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethyl­idene]ethanamine-κ3N,N′,N′′}copper(II) monohydrate

Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811004892

metal-organic compounds

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Volume 67| Part 3| March 2011| Page m334

doi:10.1107/S1600536811004892

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Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethylidene]ethanamine-κ³N,N′,N′′}copper(II) monohydrate

Nura Suleiman Gwaram,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 7 February 2011; accepted 9 February 2011; online 12 February 2011)

In the title compound, [CuCl₂(C₁₃H₁₉N₃O)]·H₂O, the tridentate Schiff base ligand and the two Cl atoms complete a distorted square-pyramidal coordination geometry around the Cu^II ion in which the three N atoms and one Cl atom are located in the basal plane and the other Cl atom is at the apical position. In the crystal, O—H⋯Cl hydrogen bonds link the complex molecules and the uncoordinated water molecules into infinite chains along the a axis. The chains are further connected into a three-dimensional network via C—H⋯O and C—H⋯Cl interactions.

Related literature

For the structures of CuCl₂ complexes with similar ligands, see: Saleh Salga et al. (2010 ); Wang et al. (2009 ). For the structure of a CdCl₂ complex with the same Schiff base ligand, see: Ikmal Hisham et al. (2010 ). For a description of the geometry of complexes with a five-coordinate metal atom, see: Addison et al. (1984 ).

Experimental

Crystal data

[CuCl₂(C₁₃H₁₉N₃O)]·H₂O
M_r = 385.77
Monoclinic, P 2₁ /n
a = 7.9194 (8) Å
b = 8.5793 (8) Å
c = 22.925 (2) Å
β = 91.981 (1)°
V = 1556.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.75 mm⁻¹
T = 100 K
0.18 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.743, T_max = 0.858
9634 measured reflections
3348 independent reflections
2948 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.060
S = 1.05
3348 reflections
197 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 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
O2—H2A⋯Cl2ⁱ	0.84 (2)	2.35 (2)	3.1829 (16)	173 (2)
O2—H2B⋯Cl1	0.83 (2)	2.48 (2)	3.2841 (18)	164 (2)
C2—H2⋯O2ⁱⁱ	0.95	2.41	3.307 (2)	156
C3—H3⋯Cl2ⁱⁱⁱ	0.95	2.82	3.619 (2)	142
C4—H4⋯O2^iv	0.95	2.50	3.445 (2)	172
C7—H7A⋯Cl1^v	0.98	2.68	3.6179 (19)	161
C8—H8A⋯O1^vi	0.99	2.47	3.336 (2)	146
C10—H10B⋯Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A⋯Cl2	0.99	2.71	3.3566 (19)	123
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) -x+2, -y+2, -z; (iv) -x+1, -y+2, -z; (v) x, y+1, z; (vi) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004892/is2674sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004892/is2674Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound consists of a copper(II) complex and one molecule of water. Like the CdCl₂ complex of the Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine, (Ikmal Hisham et al., 2010) the metal ion in the present structure is five-coordinated by the N,N',N"-tridentate Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry, the τ value (Addison et al.,1984) being 0.15. The Cu—Cl and Cu—N interatomic distances are comparable to the values reported in the literature (Saleh Salga et al., 2010; Wang et al., 2009). In the crystal, the adjacent metal complexes and water molecules are linked into a three-dimensional network via O—H···Cl, C—H···Cl and C—H···O interactions. In addition, intramolecular C—H···Cl hydrogen bonding is observed.

Related literature top

For the structures of CuCl₂ complexes with similar ligands, see: Saleh Salga et al. (2010); Wang et al. (2009). For the structure of a CdCl₂ complex with the same Schiff base ligand, see: Ikmal Hisham et al. (2010). For a description of the geometry of complexes with five-coordinate metal atom, see: Addison et al. (1984).

Experimental top

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in ethanol (20 ml) was refluxed. After 2 hr a solution of copper(II) chloride dihydrate (0.28 g, 1.65 mmol) in a minimum amount of ethanol was added and the resulting solution was refluxed for 30 min, then set aside at room temperature. The crystals of the title complex were obtained after a few days.

Computing details top

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethylidene]ethanamine- κ³N,N',N''}copper(II) monohydrate top

Crystal data top

[CuCl₂(C₁₃H₁₉N₃O)]·H₂O	F(000) = 796
M_r = 385.77	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4229 reflections
a = 7.9194 (8) Å	θ = 2.5–28.2°
b = 8.5793 (8) Å	µ = 1.75 mm⁻¹
c = 22.925 (2) Å	T = 100 K
β = 91.981 (1)°	Block, green
V = 1556.6 (3) Å³	0.18 × 0.16 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.743, T_max = 0.858	k = −10→10
9634 measured reflections	l = −29→28

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0258P)² + 0.893P] where P = (F_o² + 2F_c²)/3
3348 reflections	(Δ/σ)_max = 0.001
197 parameters	Δρ_max = 0.37 e Å⁻³
2 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[CuCl₂(C₁₃H₁₉N₃O)]·H₂O	V = 1556.6 (3) Å³
M_r = 385.77	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9194 (8) Å	µ = 1.75 mm⁻¹
b = 8.5793 (8) Å	T = 100 K
c = 22.925 (2) Å	0.18 × 0.16 × 0.09 mm
β = 91.981 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3348 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2948 reflections with I > 2σ(I)
T_min = 0.743, T_max = 0.858	R_int = 0.023
9634 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	2 restraints
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.37 e Å⁻³
3348 reflections	Δρ_min = −0.34 e Å⁻³
197 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
Cu1	0.60251 (3)	0.86379 (2)	0.122328 (9)	0.01099 (7)
Cl1	0.49087 (6)	0.62132 (5)	0.11931 (2)	0.01873 (11)
Cl2	0.90458 (6)	0.85029 (5)	0.15951 (2)	0.01773 (11)
O1	0.32231 (17)	0.82636 (16)	0.30317 (6)	0.0183 (3)
N1	0.68558 (19)	0.86674 (17)	0.03959 (7)	0.0129 (3)
N2	0.60269 (19)	1.09006 (17)	0.10733 (7)	0.0119 (3)
N3	0.51025 (18)	0.92685 (17)	0.20213 (6)	0.0114 (3)
C1	0.7350 (2)	0.7448 (2)	0.00826 (8)	0.0159 (4)
H1	0.7128	0.6427	0.0221	0.019*
C2	0.8177 (2)	0.7617 (2)	−0.04381 (8)	0.0167 (4)
H2	0.8513	0.6729	−0.0653	0.020*
C3	0.8501 (2)	0.9106 (2)	−0.06373 (8)	0.0156 (4)
H3	0.9077	0.9254	−0.0990	0.019*
C4	0.7975 (2)	1.0386 (2)	−0.03157 (8)	0.0147 (4)
H4	0.8168	1.1417	−0.0449	0.018*
C5	0.7169 (2)	1.0126 (2)	0.01989 (8)	0.0121 (4)
C6	0.6645 (2)	1.1396 (2)	0.05987 (8)	0.0127 (4)
C7	0.6910 (2)	1.3055 (2)	0.04320 (8)	0.0172 (4)
H7A	0.6395	1.3737	0.0719	0.026*
H7B	0.6385	1.3247	0.0045	0.026*
H7C	0.8124	1.3271	0.0422	0.026*
C8	0.5483 (2)	1.1856 (2)	0.15617 (8)	0.0127 (4)
H8A	0.4272	1.2127	0.1510	0.015*
H8B	0.6148	1.2832	0.1587	0.015*
C9	0.5779 (2)	1.0881 (2)	0.21117 (8)	0.0132 (4)
H9A	0.7005	1.0830	0.2210	0.016*
H9B	0.5212	1.1379	0.2442	0.016*
C10	0.5778 (2)	0.8179 (2)	0.24813 (8)	0.0139 (4)
H10A	0.7017	0.8316	0.2522	0.017*
H10B	0.5557	0.7094	0.2353	0.017*
C11	0.5017 (2)	0.8419 (2)	0.30720 (8)	0.0174 (4)
H11A	0.5492	0.7642	0.3352	0.021*
H11B	0.5316	0.9471	0.3221	0.021*
C12	0.2547 (2)	0.9419 (2)	0.26393 (8)	0.0171 (4)
H12A	0.2853	1.0468	0.2789	0.021*
H12B	0.1299	0.9340	0.2620	0.021*
C13	0.3217 (2)	0.9220 (2)	0.20293 (8)	0.0130 (4)
H13A	0.2818	0.8210	0.1867	0.016*
H13B	0.2749	1.0057	0.1774	0.016*
O2	0.0878 (2)	0.59912 (18)	0.08146 (7)	0.0273 (3)
H2A	0.035 (3)	0.659 (3)	0.1032 (10)	0.033*
H2B	0.183 (2)	0.602 (3)	0.0978 (11)	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01348 (12)	0.00927 (11)	0.01044 (12)	0.00023 (8)	0.00364 (8)	0.00007 (8)
Cl1	0.0256 (3)	0.0112 (2)	0.0200 (2)	−0.00334 (17)	0.00966 (19)	−0.00245 (17)
Cl2	0.0123 (2)	0.0245 (2)	0.0165 (2)	0.00191 (17)	0.00273 (17)	0.00437 (18)
O1	0.0157 (7)	0.0231 (7)	0.0165 (7)	−0.0002 (5)	0.0050 (5)	0.0047 (6)
N1	0.0131 (7)	0.0133 (7)	0.0124 (8)	0.0007 (6)	0.0013 (6)	0.0005 (6)
N2	0.0124 (7)	0.0112 (7)	0.0120 (8)	0.0006 (6)	0.0008 (6)	−0.0010 (6)
N3	0.0109 (7)	0.0114 (7)	0.0120 (8)	−0.0005 (6)	0.0013 (6)	−0.0006 (6)
C1	0.0190 (10)	0.0125 (9)	0.0162 (10)	0.0001 (7)	0.0019 (8)	−0.0010 (7)
C2	0.0175 (9)	0.0177 (9)	0.0151 (10)	0.0032 (7)	0.0029 (7)	−0.0031 (7)
C3	0.0142 (9)	0.0215 (10)	0.0113 (9)	0.0014 (7)	0.0017 (7)	0.0002 (7)
C4	0.0145 (9)	0.0155 (9)	0.0142 (9)	0.0001 (7)	0.0004 (7)	0.0017 (7)
C5	0.0127 (9)	0.0130 (8)	0.0107 (9)	0.0010 (7)	0.0003 (7)	−0.0004 (7)
C6	0.0108 (8)	0.0141 (9)	0.0130 (9)	0.0002 (7)	0.0003 (7)	0.0008 (7)
C7	0.0229 (10)	0.0124 (9)	0.0169 (10)	0.0016 (7)	0.0070 (8)	0.0016 (7)
C8	0.0150 (9)	0.0109 (8)	0.0124 (9)	−0.0008 (7)	0.0031 (7)	−0.0010 (7)
C9	0.0145 (9)	0.0126 (9)	0.0126 (9)	−0.0025 (7)	0.0007 (7)	−0.0029 (7)
C10	0.0127 (9)	0.0155 (9)	0.0134 (9)	0.0024 (7)	0.0007 (7)	0.0033 (7)
C11	0.0160 (9)	0.0228 (10)	0.0134 (9)	0.0002 (8)	0.0021 (7)	0.0025 (8)
C12	0.0152 (9)	0.0194 (9)	0.0171 (10)	0.0013 (7)	0.0056 (8)	−0.0004 (8)
C13	0.0099 (8)	0.0144 (9)	0.0148 (9)	−0.0005 (7)	0.0009 (7)	0.0000 (7)
O2	0.0307 (9)	0.0231 (8)	0.0285 (9)	0.0035 (7)	0.0053 (7)	−0.0013 (7)

Geometric parameters (Å, º) top

Cu1—N2	1.9715 (15)	C5—C6	1.491 (2)
Cu1—N1	2.0290 (15)	C6—C7	1.490 (2)
Cu1—N3	2.0654 (15)	C7—H7A	0.9800
Cu1—Cl1	2.2604 (5)	C7—H7B	0.9800
Cu1—Cl2	2.5143 (5)	C7—H7C	0.9800
O1—C11	1.427 (2)	C8—C9	1.524 (2)
O1—C12	1.430 (2)	C8—H8A	0.9900
N1—C1	1.336 (2)	C8—H8B	0.9900
N1—C5	1.356 (2)	C9—H9A	0.9900
N2—C6	1.281 (2)	C9—H9B	0.9900
N2—C8	1.464 (2)	C10—C11	1.515 (3)
N3—C10	1.494 (2)	C10—H10A	0.9900
N3—C13	1.495 (2)	C10—H10B	0.9900
N3—C9	1.495 (2)	C11—H11A	0.9900
C1—C2	1.389 (3)	C11—H11B	0.9900
C1—H1	0.9500	C12—C13	1.522 (3)
C2—C3	1.383 (3)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.395 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.379 (3)	O2—H2A	0.837 (16)
C4—H4	0.9500	O2—H2B	0.831 (16)

N2—Cu1—N1	79.77 (6)	C6—C7—H7B	109.5
N2—Cu1—N3	84.20 (6)	H7A—C7—H7B	109.5
N1—Cu1—N3	163.90 (6)	C6—C7—H7C	109.5
N2—Cu1—Cl1	154.62 (5)	H7A—C7—H7C	109.5
N1—Cu1—Cl1	97.01 (4)	H7B—C7—H7C	109.5
N3—Cu1—Cl1	96.79 (4)	N2—C8—C9	106.53 (14)
N2—Cu1—Cl2	95.63 (5)	N2—C8—H8A	110.4
N1—Cu1—Cl2	88.97 (5)	C9—C8—H8A	110.4
N3—Cu1—Cl2	94.20 (4)	N2—C8—H8B	110.4
Cl1—Cu1—Cl2	109.544 (19)	C9—C8—H8B	110.4
C11—O1—C12	109.02 (14)	H8A—C8—H8B	108.6
C1—N1—C5	118.92 (16)	N3—C9—C8	110.42 (14)
C1—N1—Cu1	127.12 (12)	N3—C9—H9A	109.6
C5—N1—Cu1	113.06 (12)	C8—C9—H9A	109.6
C6—N2—C8	126.51 (15)	N3—C9—H9B	109.6
C6—N2—Cu1	118.51 (13)	C8—C9—H9B	109.6
C8—N2—Cu1	114.57 (11)	H9A—C9—H9B	108.1
C10—N3—C13	107.88 (14)	N3—C10—C11	113.72 (15)
C10—N3—C9	111.29 (14)	N3—C10—H10A	108.8
C13—N3—C9	112.19 (14)	C11—C10—H10A	108.8
C10—N3—Cu1	109.42 (11)	N3—C10—H10B	108.8
C13—N3—Cu1	112.81 (11)	C11—C10—H10B	108.8
C9—N3—Cu1	103.24 (10)	H10A—C10—H10B	107.7
N1—C1—C2	122.40 (17)	O1—C11—C10	110.79 (15)
N1—C1—H1	118.8	O1—C11—H11A	109.5
C2—C1—H1	118.8	C10—C11—H11A	109.5
C3—C2—C1	118.62 (17)	O1—C11—H11B	109.5
C3—C2—H2	120.7	C10—C11—H11B	109.5
C1—C2—H2	120.7	H11A—C11—H11B	108.1
C2—C3—C4	119.35 (17)	O1—C12—C13	111.41 (15)
C2—C3—H3	120.3	O1—C12—H12A	109.3
C4—C3—H3	120.3	C13—C12—H12A	109.3
C5—C4—C3	118.75 (17)	O1—C12—H12B	109.3
C5—C4—H4	120.6	C13—C12—H12B	109.3
C3—C4—H4	120.6	H12A—C12—H12B	108.0
N1—C5—C4	121.95 (16)	N3—C13—C12	112.83 (15)
N1—C5—C6	114.30 (15)	N3—C13—H13A	109.0
C4—C5—C6	123.69 (16)	C12—C13—H13A	109.0
N2—C6—C7	126.57 (17)	N3—C13—H13B	109.0
N2—C6—C5	113.71 (16)	C12—C13—H13B	109.0
C7—C6—C5	119.70 (16)	H13A—C13—H13B	107.8
C6—C7—H7A	109.5	H2A—O2—H2B	101 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···Cl2ⁱ	0.84 (2)	2.35 (2)	3.1829 (16)	173 (2)
O2—H2B···Cl1	0.83 (2)	2.48 (2)	3.2841 (18)	164 (2)
C2—H2···O2ⁱⁱ	0.95	2.41	3.307 (2)	156
C3—H3···Cl2ⁱⁱⁱ	0.95	2.82	3.619 (2)	142
C4—H4···O2^iv	0.95	2.50	3.445 (2)	172
C7—H7A···Cl1^v	0.98	2.68	3.6179 (19)	161
C8—H8A···O1^vi	0.99	2.47	3.336 (2)	146
C10—H10B···Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A···Cl2	0.99	2.71	3.3566 (19)	123

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

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₃H₁₉N₃O)]·H₂O
M_r	385.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.9194 (8), 8.5793 (8), 22.925 (2)
β (°)	91.981 (1)
V (Å³)	1556.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.75
Crystal size (mm)	0.18 × 0.16 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.743, 0.858
No. of measured, independent and observed [I > 2σ(I)] reflections	9634, 3348, 2948
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.060, 1.05
No. of reflections	3348
No. of parameters	197
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···Cl2ⁱ	0.837 (16)	2.351 (17)	3.1829 (16)	173 (2)
O2—H2B···Cl1	0.831 (16)	2.476 (17)	3.2841 (18)	164 (2)
C2—H2···O2ⁱⁱ	0.95	2.41	3.307 (2)	156
C3—H3···Cl2ⁱⁱⁱ	0.95	2.82	3.619 (2)	142
C4—H4···O2^iv	0.95	2.50	3.445 (2)	172
C7—H7A···Cl1^v	0.98	2.68	3.6179 (19)	161
C8—H8A···O1^vi	0.99	2.47	3.336 (2)	146
C10—H10B···Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A···Cl2	0.99	2.71	3.3566 (19)	123

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

Acknowledgements

The authors thank University of Malaya for funding this study (FRGS grant No. FP004/2010B).

References

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