[(1S,2S)-2-(1-{[2-(2-Oxidobenzyl­idene­amino)­cyclo­hex­yl]imino}­eth­yl)phenolato-κ4O,N,N′,O′]copper(II)

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

doi:10.1107/S1600536810022889

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m813

doi:10.1107/S1600536810022889

Open

access

[(1S,2S)-2-(1-{[2-(2-Oxidobenzylideneamino)cyclohexyl]imino}ethyl)phenolato-κ⁴O,N,N′,O′]copper(II)

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 29 May 2010; accepted 14 June 2010; online 18 June 2010)

In the title compound, [Cu(C₂₁H₂₂N₂O₂)], the cyclohexyl ring adopts a chair conformation with the two imine groups linked at equatorial positions. The Cu^II ion is coordinated by two N atoms and two O atoms from the bis-Schiff base ligand in a slightly distorted square-planar geometry. The dihedral angle between the two benzene rings is 45.89 (9)°. The crystal structure is devoid of any classical hydrogen bonds. However, intermolecular C—H⋯O interactions are present and stabilize the structure.

Related literature

For the crystal structures of a similar symmetrical compound see: Yao et al. (1997 ). For metal complexes of unsymmetrical bis-Schiff bases, see: Lashanizadegan & Boghaei (2002 ); Rabie et al. (2008 ).

Experimental

Crystal data

[Cu(C₂₁H₂₂N₂O₂)]
M_r = 397.95
Monoclinic, P 2₁
a = 9.6699 (3) Å
b = 7.7324 (2) Å
c = 12.1847 (4) Å
β = 111.649 (2)°
V = 846.80 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.780, T_max = 0.962
9232 measured reflections
4573 independent reflections
3542 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.091
S = 0.97
4573 reflections
236 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 2036 Friedel pairs
Flack parameter: 0.050 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	1.00	2.47	3.403 (6)	155
C10—H10B⋯O2ⁱⁱ	0.99	2.45	3.366 (4)	154
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z]$ .

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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022889/pv2290sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022889/pv2290Isup2.hkl

checkCIF report

Comment top

The structure of the title complex is shown in Fig. 1. The crystal structures of a similar symmetrical compound (Yao et al., 1997) as well as metal complexes of unsymmetrical bis-schiff bases (Lashanizadegan et al., 2002; Rabie et al., 2008) have been reported.

There are no classical hydrogen bonds observed in this structure. However, there are two C—H···O type inter-molecular interactions, C9–H9..O1 and C10–H10B..O2, observed (Tab. 1) which stabilize the crystal structure.

Related literature top

For the crystal structures of a similar symmetrical compound see: Yao et al. (1997). For metal complexes of unsymmetrical bis-Schiff bases see: Lashanizadegan & Boghaei (2002); Rabie et al. (2008).

Experimental top

To an ethanolic solution (10 ml) of 1,2-diaminohexane (0.224 g, 2 mmol) was added a solution of 2-hydroxyacetophenone (0.28 g, 2 mmol) in the same solvent (10 ml). The mixture was stirred at room temperature for 15 minutes, followed by addition of 2-hydroxybenzaldehyde (0.252 g, 2 mmol) in ethanol (10 ml). The resulting yellow solution was stirred for 3 h. Then a solution of copper (II) acetate monohydrate (0.4 g, 2 mmol) in a minimum amount of ethanol was added and the solution was set aside for one day whereupon the green crystals of the title compound were obtained.

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: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level.

[(1S,2S)-2-(1-{[2-(2- Oxidobenzylideneamino)cyclohexyl]imino}ethyl)phenolato- κ⁴O,N,N',O']copper(II) top

Crystal data top

[Cu(C₂₁H₂₂N₂O₂)]	F(000) = 414
M_r = 397.95	D_x = 1.561 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1422 reflections
a = 9.6699 (3) Å	θ = 3.2–23.5°
b = 7.7324 (2) Å	µ = 1.31 mm⁻¹
c = 12.1847 (4) Å	T = 100 K
β = 111.649 (2)°	Block, green
V = 846.80 (4) Å³	0.20 × 0.10 × 0.03 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	4573 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 29.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.780, T_max = 0.962	k = −10→10
9232 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0281P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
4573 reflections	Δρ_max = 0.39 e Å⁻³
236 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.050 (15)

Crystal data top

[Cu(C₂₁H₂₂N₂O₂)]	V = 846.80 (4) Å³
M_r = 397.95	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.6699 (3) Å	µ = 1.31 mm⁻¹
b = 7.7324 (2) Å	T = 100 K
c = 12.1847 (4) Å	0.20 × 0.10 × 0.03 mm
β = 111.649 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4573 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3542 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.962	R_int = 0.053
9232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.39 e Å⁻³
S = 0.97	Δρ_min = −0.37 e Å⁻³
4573 reflections	Absolute structure: Flack (1983), 2036 Friedel pairs
236 parameters	Absolute structure parameter: 0.050 (15)
1 restraint

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	0.09681 (4)	0.25280 (6)	0.05446 (3)	0.01389 (10)
O1	0.1603 (3)	0.2029 (3)	−0.0696 (2)	0.0199 (7)
O2	0.2941 (3)	0.3130 (3)	0.1540 (2)	0.0179 (6)
N1	−0.1155 (3)	0.2570 (8)	−0.0484 (2)	0.0158 (5)
N2	0.0262 (3)	0.2546 (7)	0.1826 (2)	0.0148 (5)
C1	0.0826 (4)	0.2231 (4)	−0.1822 (3)	0.0146 (8)
C2	0.1533 (4)	0.1917 (5)	−0.2626 (4)	0.0210 (9)
H2	0.2528	0.1501	−0.2330	0.025*
C3	0.0850 (4)	0.2184 (5)	−0.3815 (3)	0.0239 (10)
H3	0.1355	0.1914	−0.4331	0.029*
C4	−0.0588 (4)	0.2855 (5)	−0.4267 (3)	0.0250 (11)
H4	−0.1056	0.3099	−0.5085	0.030*
C5	−0.1319 (4)	0.3158 (5)	−0.3509 (3)	0.0206 (8)
H5	−0.2306	0.3595	−0.3825	0.025*
C6	−0.0671 (4)	0.2850 (4)	−0.2290 (3)	0.0142 (9)
C7	−0.1594 (4)	0.3112 (4)	−0.1567 (3)	0.0143 (7)
C8	−0.3037 (4)	0.4067 (5)	−0.2152 (4)	0.0250 (10)
H8A	−0.3788	0.3272	−0.2664	0.038*
H8B	−0.2886	0.5021	−0.2625	0.038*
H8C	−0.3378	0.4531	−0.1546	0.038*
C9	−0.2129 (3)	0.2699 (6)	0.0225 (3)	0.0135 (7)
H9	−0.2298	0.3943	0.0363	0.016*
C10	−0.3627 (4)	0.1763 (5)	−0.0305 (3)	0.0185 (8)
H10A	−0.4222	0.2286	−0.1078	0.022*
H10B	−0.3457	0.0531	−0.0438	0.022*
C11	−0.4481 (4)	0.1894 (5)	0.0520 (3)	0.0198 (8)
H11A	−0.4679	0.3125	0.0631	0.024*
H11B	−0.5450	0.1296	0.0162	0.024*
C12	−0.3605 (4)	0.1086 (5)	0.1712 (4)	0.0223 (9)
H12A	−0.3504	−0.0172	0.1611	0.027*
H12B	−0.4156	0.1250	0.2247	0.027*
C13	−0.2067 (4)	0.1891 (5)	0.2264 (3)	0.0189 (8)
H13A	−0.1487	0.1261	0.2998	0.023*
H13B	−0.2163	0.3110	0.2474	0.023*
C14	−0.1252 (4)	0.1816 (5)	0.1409 (3)	0.0164 (8)
H14	−0.1162	0.0566	0.1234	0.020*
C15	0.0955 (4)	0.3110 (4)	0.2870 (3)	0.0174 (8)
H15	0.0441	0.3094	0.3401	0.021*
C16	0.2456 (4)	0.3770 (4)	0.3309 (3)	0.0155 (8)
C17	0.3008 (4)	0.4505 (5)	0.4447 (3)	0.0206 (9)
H17	0.2403	0.4492	0.4908	0.025*
C18	0.4390 (4)	0.5235 (5)	0.4905 (4)	0.0221 (9)
H18	0.4736	0.5739	0.5670	0.026*
C19	0.5288 (4)	0.5227 (5)	0.4230 (4)	0.0222 (9)
H19	0.6250	0.5734	0.4539	0.027*
C20	0.4793 (4)	0.4495 (5)	0.3123 (3)	0.0187 (8)
H20	0.5437	0.4474	0.2694	0.022*
C21	0.3353 (4)	0.3770 (5)	0.2605 (3)	0.0174 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01095 (17)	0.01506 (18)	0.0154 (2)	0.0002 (3)	0.00449 (14)	0.0004 (3)
O1	0.0160 (13)	0.0234 (17)	0.0211 (15)	0.0011 (10)	0.0077 (12)	−0.0015 (10)
O2	0.0134 (12)	0.0244 (14)	0.0159 (14)	−0.0023 (11)	0.0054 (11)	−0.0004 (10)
N1	0.0127 (13)	0.0195 (13)	0.0160 (13)	0.000 (2)	0.0061 (11)	−0.002 (2)
N2	0.0099 (12)	0.0176 (12)	0.0156 (13)	0.002 (2)	0.0033 (10)	0.000 (2)
C1	0.0217 (17)	0.004 (2)	0.0186 (18)	−0.0023 (14)	0.0084 (15)	−0.0016 (13)
C2	0.0205 (19)	0.0154 (18)	0.030 (2)	0.0004 (15)	0.0132 (18)	−0.0034 (16)
C3	0.033 (2)	0.020 (3)	0.025 (2)	−0.0004 (17)	0.0173 (18)	−0.0067 (16)
C4	0.033 (2)	0.024 (3)	0.0184 (19)	−0.0016 (18)	0.0100 (17)	−0.0004 (16)
C5	0.0200 (19)	0.0220 (18)	0.019 (2)	−0.0013 (16)	0.0060 (16)	0.0010 (15)
C6	0.0173 (17)	0.007 (2)	0.0190 (18)	−0.0004 (14)	0.0078 (14)	−0.0013 (13)
C7	0.0124 (17)	0.0111 (16)	0.0185 (19)	−0.0032 (13)	0.0045 (15)	−0.0039 (14)
C8	0.019 (2)	0.028 (2)	0.024 (2)	−0.0011 (18)	0.0031 (18)	−0.0012 (17)
C9	0.0119 (14)	0.0145 (19)	0.0157 (16)	0.0038 (18)	0.0071 (12)	0.0025 (18)
C10	0.0129 (18)	0.0211 (19)	0.021 (2)	−0.0027 (16)	0.0060 (16)	−0.0062 (16)
C11	0.0145 (18)	0.0249 (19)	0.021 (2)	−0.0025 (15)	0.0072 (17)	−0.0032 (15)
C12	0.017 (2)	0.021 (2)	0.032 (3)	−0.0038 (17)	0.0125 (19)	0.0007 (17)
C13	0.0188 (19)	0.0209 (18)	0.019 (2)	0.0016 (15)	0.0094 (16)	0.0028 (15)
C14	0.0138 (18)	0.0137 (17)	0.022 (2)	0.0013 (15)	0.0071 (16)	0.0000 (15)
C15	0.0136 (18)	0.0157 (18)	0.023 (2)	0.0034 (14)	0.0070 (16)	0.0025 (15)
C16	0.0151 (19)	0.0120 (17)	0.016 (2)	−0.0011 (15)	0.0023 (15)	0.0047 (14)
C17	0.019 (2)	0.0207 (19)	0.018 (2)	0.0039 (16)	0.0023 (17)	0.0016 (16)
C18	0.021 (2)	0.021 (2)	0.019 (2)	−0.0014 (17)	0.0010 (17)	−0.0038 (17)
C19	0.013 (2)	0.017 (2)	0.028 (2)	−0.0020 (16)	−0.0015 (17)	0.0030 (17)
C20	0.0131 (19)	0.0179 (19)	0.024 (2)	0.0001 (15)	0.0049 (17)	0.0045 (16)
C21	0.0160 (19)	0.0141 (18)	0.020 (2)	−0.0014 (15)	0.0049 (16)	0.0050 (15)

Geometric parameters (Å, º) top

Cu1—O1	1.870 (2)	C9—H9	1.0000
Cu1—O2	1.903 (2)	C10—C11	1.522 (5)
Cu1—N2	1.921 (2)	C10—H10A	0.9900
Cu1—N1	1.972 (3)	C10—H10B	0.9900
O1—C1	1.307 (4)	C11—C12	1.519 (5)
O2—C21	1.306 (4)	C11—H11A	0.9900
N1—C7	1.298 (5)	C11—H11B	0.9900
N1—C9	1.498 (4)	C12—C13	1.521 (5)
N2—C15	1.277 (4)	C12—H12A	0.9900
N2—C14	1.474 (4)	C12—H12B	0.9900
C1—C2	1.407 (5)	C13—C14	1.522 (5)
C1—C6	1.429 (5)	C13—H13A	0.9900
C2—C3	1.368 (5)	C13—H13B	0.9900
C2—H2	0.9500	C14—H14	1.0000
C3—C4	1.394 (5)	C15—C16	1.443 (5)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.374 (5)	C16—C17	1.409 (5)
C4—H4	0.9500	C16—C21	1.427 (5)
C5—C6	1.403 (5)	C17—C18	1.366 (5)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.481 (5)	C18—C19	1.400 (6)
C7—C8	1.506 (5)	C18—H18	0.9500
C8—H8A	0.9800	C19—C20	1.376 (5)
C8—H8B	0.9800	C19—H19	0.9500
C8—H8C	0.9800	C20—C21	1.415 (5)
C9—C10	1.533 (5)	C20—H20	0.9500
C9—C14	1.538 (5)

O1—Cu1—O2	90.86 (11)	C9—C10—H10A	109.6
O1—Cu1—N2	168.46 (17)	C11—C10—H10B	109.6
O2—Cu1—N2	93.06 (11)	C9—C10—H10B	109.6
O1—Cu1—N1	93.73 (11)	H10A—C10—H10B	108.1
O2—Cu1—N1	164.81 (18)	C12—C11—C10	111.0 (3)
N2—Cu1—N1	85.27 (10)	C12—C11—H11A	109.4
C1—O1—Cu1	126.2 (2)	C10—C11—H11A	109.4
C21—O2—Cu1	126.4 (2)	C12—C11—H11B	109.4
C7—N1—C9	121.7 (3)	C10—C11—H11B	109.4
C7—N1—Cu1	121.6 (2)	H11A—C11—H11B	108.0
C9—N1—Cu1	111.31 (19)	C11—C12—C13	111.4 (3)
C15—N2—C14	124.3 (3)	C11—C12—H12A	109.4
C15—N2—Cu1	126.9 (3)	C13—C12—H12A	109.4
C14—N2—Cu1	108.9 (2)	C11—C12—H12B	109.4
O1—C1—C2	118.1 (3)	C13—C12—H12B	109.4
O1—C1—C6	124.3 (3)	H12A—C12—H12B	108.0
C2—C1—C6	117.4 (3)	C12—C13—C14	110.5 (3)
C3—C2—C1	122.9 (4)	C12—C13—H13A	109.6
C3—C2—H2	118.6	C14—C13—H13A	109.6
C1—C2—H2	118.6	C12—C13—H13B	109.6
C2—C3—C4	119.7 (3)	C14—C13—H13B	109.6
C2—C3—H3	120.1	H13A—C13—H13B	108.1
C4—C3—H3	120.1	N2—C14—C13	116.7 (3)
C5—C4—C3	118.9 (4)	N2—C14—C9	106.7 (3)
C5—C4—H4	120.5	C13—C14—C9	112.3 (3)
C3—C4—H4	120.5	N2—C14—H14	106.9
C4—C5—C6	122.9 (4)	C13—C14—H14	106.9
C4—C5—H5	118.5	C9—C14—H14	106.9
C6—C5—H5	118.5	N2—C15—C16	125.2 (3)
C5—C6—C1	118.0 (3)	N2—C15—H15	117.4
C5—C6—C7	118.4 (3)	C16—C15—H15	117.4
C1—C6—C7	123.5 (3)	C17—C16—C21	119.9 (3)
N1—C7—C6	121.2 (3)	C17—C16—C15	118.1 (4)
N1—C7—C8	122.5 (3)	C21—C16—C15	122.0 (3)
C6—C7—C8	116.3 (3)	C18—C17—C16	121.9 (4)
C7—C8—H8A	109.5	C18—C17—H17	119.1
C7—C8—H8B	109.5	C16—C17—H17	119.1
H8A—C8—H8B	109.5	C17—C18—C19	118.9 (4)
C7—C8—H8C	109.5	C17—C18—H18	120.6
H8A—C8—H8C	109.5	C19—C18—H18	120.6
H8B—C8—H8C	109.5	C20—C19—C18	120.7 (4)
N1—C9—C10	115.0 (3)	C20—C19—H19	119.6
N1—C9—C14	105.4 (3)	C18—C19—H19	119.6
C10—C9—C14	107.1 (3)	C19—C20—C21	122.0 (4)
N1—C9—H9	109.7	C19—C20—H20	119.0
C10—C9—H9	109.7	C21—C20—H20	119.0
C14—C9—H9	109.7	O2—C21—C20	118.9 (4)
C11—C10—C9	110.4 (3)	O2—C21—C16	124.5 (3)
C11—C10—H10A	109.6	C20—C21—C16	116.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	1.00	2.47	3.403 (6)	155
C10—H10B···O2ⁱⁱ	0.99	2.45	3.366 (4)	154

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂₁H₂₂N₂O₂)]
M_r	397.95
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	9.6699 (3), 7.7324 (2), 12.1847 (4)
β (°)	111.649 (2)
V (Å³)	846.80 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.20 × 0.10 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.780, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	9232, 4573, 3542
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.091, 0.97
No. of reflections	4573
No. of parameters	236
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37
Absolute structure	Flack (1983), 2036 Friedel pairs
Absolute structure parameter	0.050 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	1.00	2.47	3.403 (6)	155
C10—H10B···O2ⁱⁱ	0.99	2.45	3.366 (4)	154

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

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lashanizadegan, M. & Boghaei, D. M. (2002). Synth. React. Inorg. Met. Org. Chem. 32, 345–355. Web of Science CSD CrossRef CAS Google Scholar
Rabie, U. M., Assran, A. S. A. & Abou-El-Wafa, M. H. M. (2008). J. Mol. Struct. 872, 113–122. Web of Science 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
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar
Yao, H. H., Huang, W. T., Lo, J. M., Liao, F. L. & Wang, S. L. (1997). Eur. J. Solid State Inorg. Chem. 34, 355–366. 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.