Aqua­{2-morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3N,N′,N′′}bis­(thio­cyanato-κN)cobalt(II)

Suleiman Gwaram, N.; Ikmal Hisham, N.A.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S160053681100136X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m205

doi:10.1107/S160053681100136X

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Aqua{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N′,N′′}bis(thiocyanato-κN)cobalt(II)

Nura Suleiman Gwaram,^a Nurul Azimah Ikmal Hisham,^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 30 December 2010; accepted 10 January 2011; online 15 January 2011)

In the title complex, [Co(NCS)₂(C₁₃H₁₉N₃O)(H₂O)], the Co^II ion is six-coordinated by the N,N′,N′′-tridentate Schiff base, the N atoms of two thiocyanate ligands and one water molecule in a distorted octahedral geometry. Intramolecular C—H⋯N and C—H⋯O hydrogen bonds occur. In the crystal, intermolecular O—H⋯O, O—H⋯S, C—H⋯S and S⋯S [3.5546 (18) Å] interactions result in an infinite three-dimensional network.

Related literature

For the crystal structure of the analogous Ni^II complex, see: Suleiman Gwaram et al. (2011 ). For a similar Co(II) complex, see: Sun et al. (2007 ).

Experimental

Crystal data

[Co(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]
M_r = 426.42
Monoclinic, P 2₁ /c
a = 7.1554 (3) Å
b = 22.187 (1) Å
c = 12.1297 (5) Å
β = 91.115 (3)°
V = 1925.31 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 100 K
0.18 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.823, T_max = 0.915
13017 measured reflections
3401 independent reflections
2662 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.137
S = 1.08
3401 reflections
233 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.83 (3)	1.88 (3)	2.701 (4)	172 (5)
O2—H2B⋯S1ⁱⁱ	0.83 (3)	2.36 (3)	3.161 (3)	162 (5)
C11—H11A⋯O2	0.99	2.40	3.121 (6)	130
C12—H12B⋯N4	0.99	2.62	3.511 (7)	150
C2—H2⋯S1ⁱ	0.95	2.85	3.774 (6)	165
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, 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: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100136X/pv2377sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100136X/pv2377Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title Co^II complex is isostructural with the previously reported Ni^II complex (Suleiman Gwaram et al., 2011). The Schiff base, prepared in situ, acts as an N,N',N''-tridentate ligand towards the Co^II ion to form two five-membered chelate rings with the metal atom. Two cis-located isothiocyanate and one water molecule complete a distorted octahedral geometry around the Co(II) center. A similar arrangement was observed in a related Co^II complex (Sun et al., 2007). The molecular structure contains intramolecular C—H···N and C—H···O hydrogen bonds. In the crystal, the adjacent molecules are connected via O—H···O, O—H···S, C—H···S hydrogen bonds into infinite layers parallel to the ac plane. The layers are further linked into a three-dimensional polymeric structure through an S···S interaction [3.5546 (18) Å] between S1 and S2 of the symmetry related molecule at –x+1, y - 1/2, -z + 3/2.

Related literature top

For the crystal structure of the analogous Ni^II complex, see: Suleiman Gwaram et al. (2011). For a similar Co(II) complex, see: Sun et al. (2007).

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 for 2 hr followed by addition of a solution of cobalt(II) acetate tetrahydrate (0.41 g, 1.65 mmol) and sodium thiocyanete (0.134 g, 1.65 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then left at room temperature. The crystals of the title complex were obtained in 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. Thermal ellipsoid plot of the title compound at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

Aqua{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N',N''}bis(thiocyanato-κN)cobalt(II) top

Crystal data top

[Co(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]	F(000) = 884
M_r = 426.42	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2128 reflections
a = 7.1554 (3) Å	θ = 2.5–23.4°
b = 22.187 (1) Å	µ = 1.13 mm⁻¹
c = 12.1297 (5) Å	T = 100 K
β = 91.115 (3)°	Rod, red
V = 1925.31 (14) Å³	0.18 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	2662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.823, T_max = 0.915	k = −26→26
13017 measured reflections	l = −14→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0626P)² + 2.7605P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.79 e Å⁻³
3 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Co(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]	V = 1925.31 (14) Å³
M_r = 426.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1554 (3) Å	µ = 1.13 mm⁻¹
b = 22.187 (1) Å	T = 100 K
c = 12.1297 (5) Å	0.18 × 0.10 × 0.08 mm
β = 91.115 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3401 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2662 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.915	R_int = 0.062
13017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	3 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.79 e Å⁻³
3401 reflections	Δρ_min = −0.54 e Å⁻³
233 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
Co1	0.14436 (7)	0.37659 (2)	0.77043 (5)	0.01682 (19)
S1	0.62351 (16)	0.22817 (6)	0.78138 (16)	0.0511 (5)
S2	0.40771 (17)	0.56976 (6)	0.67930 (12)	0.0357 (3)
O1	0.1265 (5)	0.29112 (14)	0.4482 (3)	0.0315 (8)
O2	0.0220 (4)	0.28962 (14)	0.7921 (3)	0.0248 (7)
H2A	0.063 (7)	0.2640 (18)	0.836 (3)	0.030*
H2B	−0.091 (4)	0.282 (2)	0.788 (4)	0.030*
N1	0.1427 (5)	0.38088 (16)	0.9493 (3)	0.0240 (8)
N2	−0.1063 (4)	0.41983 (16)	0.8045 (3)	0.0195 (8)
N3	0.0131 (5)	0.38505 (15)	0.5984 (3)	0.0180 (8)
N4	0.3878 (5)	0.32766 (17)	0.7616 (3)	0.0273 (9)
N5	0.2780 (5)	0.45788 (16)	0.7493 (3)	0.0227 (8)
C1	0.2665 (7)	0.3574 (2)	1.0199 (4)	0.0345 (12)
H1	0.3780	0.3403	0.9924	0.041*
C2	0.2382 (10)	0.3571 (3)	1.1326 (5)	0.0522 (17)
H2	0.3300	0.3407	1.1817	0.063*
C3	0.0743 (11)	0.3811 (3)	1.1727 (5)	0.064 (2)
H3	0.0506	0.3807	1.2495	0.076*
C4	−0.0533 (9)	0.4055 (3)	1.0995 (4)	0.0449 (14)
H4	−0.1662	0.4224	1.1255	0.054*
C5	−0.0178 (6)	0.4054 (2)	0.9889 (4)	0.0271 (11)
C6	−0.1499 (6)	0.4296 (2)	0.9038 (4)	0.0269 (11)
C7	−0.3223 (7)	0.4624 (3)	0.9403 (5)	0.0456 (15)
H7A	−0.3986	0.4735	0.8755	0.068*
H7B	−0.2855	0.4989	0.9808	0.068*
H7C	−0.3949	0.4361	0.9883	0.068*
C8	−0.2204 (6)	0.4400 (2)	0.7098 (4)	0.0246 (10)
H8A	−0.2712	0.4807	0.7241	0.030*
H8B	−0.3265	0.4120	0.6974	0.030*
C9	−0.0980 (6)	0.4413 (2)	0.6091 (4)	0.0223 (10)
H9A	−0.1778	0.4466	0.5423	0.027*
H9B	−0.0121	0.4762	0.6145	0.027*
C10	−0.1111 (6)	0.33506 (19)	0.5629 (4)	0.0232 (10)
H10A	−0.1853	0.3478	0.4973	0.028*
H10B	−0.1992	0.3259	0.6226	0.028*
C11	−0.0029 (7)	0.2791 (2)	0.5357 (4)	0.0279 (11)
H11A	0.0669	0.2650	0.6021	0.033*
H11B	−0.0905	0.2468	0.5124	0.033*
C12	0.2525 (7)	0.3375 (2)	0.4824 (4)	0.0296 (11)
H12A	0.3422	0.3452	0.4229	0.036*
H12B	0.3243	0.3238	0.5483	0.036*
C13	0.1525 (7)	0.3950 (2)	0.5091 (4)	0.0255 (10)
H13A	0.0872	0.4103	0.4420	0.031*
H13B	0.2446	0.4258	0.5334	0.031*
C14	0.4866 (6)	0.2874 (2)	0.7706 (4)	0.0297 (11)
C15	0.3316 (5)	0.5040 (2)	0.7189 (4)	0.0192 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0109 (3)	0.0182 (3)	0.0215 (3)	0.0007 (2)	0.0026 (2)	0.0016 (2)
S1	0.0148 (6)	0.0235 (7)	0.1153 (15)	0.0026 (5)	0.0068 (7)	0.0148 (8)
S2	0.0273 (6)	0.0273 (7)	0.0523 (9)	−0.0060 (5)	−0.0027 (6)	0.0136 (6)
O1	0.0404 (19)	0.0304 (18)	0.0242 (18)	−0.0125 (15)	0.0143 (15)	−0.0108 (14)
O2	0.0200 (15)	0.0262 (18)	0.0281 (19)	−0.0045 (14)	−0.0035 (14)	0.0116 (14)
N1	0.0224 (19)	0.0220 (19)	0.028 (2)	−0.0062 (16)	−0.0038 (16)	0.0029 (17)
N2	0.0141 (17)	0.026 (2)	0.018 (2)	0.0001 (15)	0.0031 (15)	−0.0023 (16)
N3	0.0214 (18)	0.0158 (18)	0.0170 (19)	−0.0014 (14)	0.0049 (15)	0.0010 (15)
N4	0.0164 (18)	0.027 (2)	0.039 (3)	0.0032 (17)	0.0019 (17)	0.0030 (18)
N5	0.0175 (18)	0.020 (2)	0.030 (2)	−0.0011 (16)	0.0022 (16)	0.0015 (17)
C1	0.043 (3)	0.027 (3)	0.033 (3)	−0.004 (2)	−0.016 (2)	0.000 (2)
C2	0.088 (5)	0.035 (3)	0.033 (3)	−0.003 (3)	−0.034 (3)	0.003 (3)
C3	0.108 (6)	0.065 (4)	0.018 (3)	0.005 (4)	0.001 (3)	−0.010 (3)
C4	0.065 (4)	0.053 (3)	0.017 (3)	−0.001 (3)	0.007 (3)	−0.007 (2)
C5	0.028 (2)	0.033 (3)	0.020 (3)	−0.009 (2)	0.003 (2)	−0.006 (2)
C6	0.017 (2)	0.035 (3)	0.028 (3)	−0.005 (2)	0.0004 (19)	−0.006 (2)
C7	0.021 (2)	0.071 (4)	0.045 (4)	0.004 (3)	0.011 (2)	−0.021 (3)
C8	0.018 (2)	0.026 (2)	0.030 (3)	0.0068 (18)	−0.0023 (19)	−0.003 (2)
C9	0.024 (2)	0.025 (2)	0.018 (2)	0.0018 (19)	−0.0060 (18)	0.0027 (19)
C10	0.027 (2)	0.022 (2)	0.020 (2)	−0.0041 (19)	−0.0013 (19)	0.0022 (19)
C11	0.035 (3)	0.028 (3)	0.022 (3)	−0.009 (2)	0.008 (2)	−0.002 (2)
C12	0.033 (3)	0.029 (3)	0.028 (3)	−0.011 (2)	0.017 (2)	−0.009 (2)
C13	0.035 (3)	0.026 (2)	0.016 (2)	−0.008 (2)	0.008 (2)	−0.0005 (19)
C14	0.016 (2)	0.025 (3)	0.049 (3)	−0.007 (2)	0.002 (2)	0.004 (2)
C15	0.0111 (19)	0.025 (2)	0.021 (2)	0.0056 (18)	−0.0041 (17)	−0.0041 (19)

Geometric parameters (Å, º) top

Co1—N4	2.057 (4)	C3—C4	1.372 (9)
Co1—N5	2.060 (4)	C3—H3	0.9500
Co1—N2	2.083 (3)	C4—C5	1.371 (7)
Co1—O2	2.137 (3)	C4—H4	0.9500
Co1—N1	2.171 (4)	C5—C6	1.486 (7)
Co1—N3	2.279 (4)	C6—C7	1.507 (6)
S1—C14	1.642 (5)	C7—H7A	0.9800
S2—C15	1.633 (5)	C7—H7B	0.9800
O1—C12	1.424 (5)	C7—H7C	0.9800
O1—C11	1.446 (5)	C8—C9	1.517 (6)
O2—H2A	0.83 (3)	C8—H8A	0.9900
O2—H2B	0.83 (3)	C8—H8B	0.9900
N1—C1	1.327 (6)	C9—H9A	0.9900
N1—C5	1.366 (6)	C9—H9B	0.9900
N2—C6	1.269 (6)	C10—C11	1.504 (6)
N2—C8	1.465 (6)	C10—H10A	0.9900
N3—C10	1.480 (5)	C10—H10B	0.9900
N3—C9	1.487 (5)	C11—H11A	0.9900
N3—C13	1.503 (5)	C11—H11B	0.9900
N4—C14	1.144 (6)	C12—C13	1.501 (6)
N5—C15	1.155 (5)	C12—H12A	0.9900
C1—C2	1.386 (8)	C12—H12B	0.9900
C1—H1	0.9500	C13—H13A	0.9900
C2—C3	1.385 (9)	C13—H13B	0.9900
C2—H2	0.9500

N4—Co1—N5	93.44 (14)	N2—C6—C5	115.7 (4)
N4—Co1—N2	170.73 (15)	N2—C6—C7	125.4 (5)
N5—Co1—N2	91.43 (14)	C5—C6—C7	118.9 (4)
N4—Co1—O2	83.07 (14)	C6—C7—H7A	109.5
N5—Co1—O2	176.51 (13)	C6—C7—H7B	109.5
N2—Co1—O2	92.01 (13)	H7A—C7—H7B	109.5
N4—Co1—N1	95.53 (15)	C6—C7—H7C	109.5
N5—Co1—N1	95.59 (14)	H7A—C7—H7C	109.5
N2—Co1—N1	76.14 (14)	H7B—C7—H7C	109.5
O2—Co1—N1	84.63 (13)	N2—C8—C9	108.4 (3)
N4—Co1—N3	109.26 (15)	N2—C8—H8A	110.0
N5—Co1—N3	89.88 (13)	C9—C8—H8A	110.0
N2—Co1—N3	78.61 (13)	N2—C8—H8B	110.0
O2—Co1—N3	91.41 (12)	C9—C8—H8B	110.0
N1—Co1—N3	154.27 (13)	H8A—C8—H8B	108.4
C12—O1—C11	109.3 (3)	N3—C9—C8	111.9 (3)
Co1—O2—H2A	124 (4)	N3—C9—H9A	109.2
Co1—O2—H2B	126 (3)	C8—C9—H9A	109.2
H2A—O2—H2B	103 (5)	N3—C9—H9B	109.2
C1—N1—C5	118.9 (4)	C8—C9—H9B	109.2
C1—N1—Co1	127.7 (3)	H9A—C9—H9B	107.9
C5—N1—Co1	112.9 (3)	N3—C10—C11	112.0 (4)
C6—N2—C8	123.3 (4)	N3—C10—H10A	109.2
C6—N2—Co1	119.7 (3)	C11—C10—H10A	109.2
C8—N2—Co1	117.0 (3)	N3—C10—H10B	109.2
C10—N3—C9	109.6 (3)	C11—C10—H10B	109.2
C10—N3—C13	107.7 (3)	H10A—C10—H10B	107.9
C9—N3—C13	107.7 (3)	O1—C11—C10	110.4 (4)
C10—N3—Co1	116.0 (3)	O1—C11—H11A	109.6
C9—N3—Co1	101.6 (2)	C10—C11—H11A	109.6
C13—N3—Co1	113.9 (3)	O1—C11—H11B	109.6
C14—N4—Co1	158.4 (4)	C10—C11—H11B	109.6
C15—N5—Co1	166.6 (4)	H11A—C11—H11B	108.1
N1—C1—C2	122.1 (5)	O1—C12—C13	112.0 (4)
N1—C1—H1	119.0	O1—C12—H12A	109.2
C2—C1—H1	119.0	C13—C12—H12A	109.2
C3—C2—C1	119.1 (5)	O1—C12—H12B	109.2
C3—C2—H2	120.5	C13—C12—H12B	109.2
C1—C2—H2	120.5	H12A—C12—H12B	107.9
C4—C3—C2	118.8 (5)	C12—C13—N3	110.8 (3)
C4—C3—H3	120.6	C12—C13—H13A	109.5
C2—C3—H3	120.6	N3—C13—H13A	109.5
C5—C4—C3	120.0 (6)	C12—C13—H13B	109.5
C5—C4—H4	120.0	N3—C13—H13B	109.5
C3—C4—H4	120.0	H13A—C13—H13B	108.1
N1—C5—C4	121.2 (5)	N4—C14—S1	178.1 (5)
N1—C5—C6	115.3 (4)	N5—C15—S2	178.5 (4)
C4—C5—C6	123.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.83 (3)	1.88 (3)	2.701 (4)	172 (5)
O2—H2B···S1ⁱⁱ	0.83 (3)	2.36 (3)	3.161 (3)	162 (5)
C11—H11A···O2	0.99	2.40	3.121 (6)	130
C12—H12B···N4	0.99	2.62	3.511 (7)	150
C2—H2···S1ⁱ	0.95	2.85	3.774 (6)	165

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

Experimental details

Crystal data
Chemical formula	[Co(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]
M_r	426.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.1554 (3), 22.187 (1), 12.1297 (5)
β (°)	91.115 (3)
V (Å³)	1925.31 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.18 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.823, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	13017, 3401, 2662
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.137, 1.08
No. of reflections	3401
No. of parameters	233
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.54

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···O1ⁱ	0.83 (3)	1.88 (3)	2.701 (4)	172 (5)
O2—H2B···S1ⁱⁱ	0.83 (3)	2.36 (3)	3.161 (3)	162 (5)
C11—H11A···O2	0.99	2.40	3.121 (6)	130
C12—H12B···N4	0.99	2.62	3.511 (7)	150
C2—H2···S1ⁱ	0.95	2.85	3.774 (6)	165

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

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant FP004/2010B).

References

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