Aqua{2-(morpholin-4-yl)-N-[1-(2-pyri­dyl)ethyl­idene]ethanamine-κ3N,N′,N′′}bis­(thio­cyanato-κN)manganese(II)

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

doi:10.1107/S1600536811022124

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m928

doi:10.1107/S1600536811022124

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Aqua{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N′,N′′}bis(thiocyanato-κN)manganese(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 31 May 2011; accepted 7 June 2011; online 18 June 2011)

In the title compound, [Mn(NCS)₂(C₁₃H₁₉N₃O)(H₂O)], the Schiff base acts as an N,N′,N"-tridentate ligand, forming two five-membered chelating rings with the Mn^II atom. The distorted octahedral geometry around the metal atom is completed by two cis-positioned N-bound thiocyanate ligands and one water molecule. In the crystal, adjacent molecules are linked through O—H⋯O, O—H⋯S and C—H⋯S hydrogen bonds into a three-dimensional supra-molecular structure. An intramolecular C—H⋯O hydrogen bond also occurs.

Related literature

For the isostructural Co(II) complex, see: Suleiman Gwaram et al. (2011 ).

Experimental

Crystal data

[Mn(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]
M_r = 422.43
Monoclinic, P 2₁ /c
a = 7.1837 (13) Å
b = 22.408 (4) Å
c = 12.112 (2) Å
β = 91.149 (3)°
V = 1949.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 100 K
0.19 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.846, T_max = 0.931
11816 measured reflections
4235 independent reflections
3197 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.082
S = 1.01
4235 reflections
233 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N1	2.2835 (19)
Mn1—N2	2.2115 (18)
Mn1—N3	2.3891 (19)
Mn1—N4	2.137 (2)
Mn1—N5	2.145 (2)
Mn1—O2	2.2117 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯S1ⁱ	0.82 (2)	2.38 (2)	3.1910 (18)	169 (2)
O2—H2B⋯O1ⁱⁱ	0.82 (2)	1.89 (2)	2.693 (2)	164 (3)
C11—H11A⋯O2	0.99	2.41	3.179 (3)	134
C12—H12A⋯S2ⁱⁱⁱ	0.99	2.82	3.674 (2)	145
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+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/S1600536811022124/xu5237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022124/xu5237Isup2.hkl

checkCIF report

Comment top

The crystal of the title compound is isostructural with the previously reported Co^II complex (Suleiman Gwaram et al., 2011). The metal center is coordinated by the N,N',N"-tridentate Schiff base, two N-donor thiocyanates and one water O atom in a distorted octahedral geometry. In the crystal, the molecules are linked through O—H···O and O—H···S hydrogen bonds into layers parallel to the ac plane and theses are connected into a three-dimensional network via C—H···S interactions. Moreover, intramolecular C—H···O hydrogen bonding is observed.

Related literature top

For the isostructural Co(II) complex, see: Suleiman Gwaram et al. (2011).

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 manganese(II) acetate tetrahydrate (0.41 g, 1.65 mmol) and ammonium thiocyanate (0.13 g, 1.65 mmol) in a minimum amount of ethanol. The resulting solution was refluxed for 30 min, and then left at room temperature. The crystals of the title complex were obtained in a week.

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. Molecular structure of the title compound with thermal ellipsoids at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Aqua{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine- κ³N,N',N''}bis(thiocyanato-κN)manganese(II) top

Crystal data top

[Mn(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]	F(000) = 876
M_r = 422.43	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2405 reflections
a = 7.1837 (13) Å	θ = 2.5–27.0°
b = 22.408 (4) Å	µ = 0.91 mm⁻¹
c = 12.112 (2) Å	T = 100 K
β = 91.149 (3)°	Prismatic, brown
V = 1949.3 (6) Å³	0.19 × 0.16 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	3197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.846, T_max = 0.931	k = −28→15
11816 measured reflections	l = −13→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0302P)² + 0.8463P] where P = (F_o² + 2F_c²)/3
4235 reflections	(Δ/σ)_max = 0.010
233 parameters	Δρ_max = 0.33 e Å⁻³
3 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Mn(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]	V = 1949.3 (6) Å³
M_r = 422.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1837 (13) Å	µ = 0.91 mm⁻¹
b = 22.408 (4) Å	T = 100 K
c = 12.112 (2) Å	0.19 × 0.16 × 0.08 mm
β = 91.149 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4235 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3197 reflections with I > 2σ(I)
T_min = 0.846, T_max = 0.931	R_int = 0.040
11816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	3 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.33 e Å⁻³
4235 reflections	Δρ_min = −0.46 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
Mn1	0.32353 (4)	0.376455 (15)	0.71236 (3)	0.01469 (10)
S1	−0.15046 (9)	0.22409 (3)	0.71859 (8)	0.0455 (2)
S2	0.08739 (9)	0.56599 (3)	0.84034 (6)	0.03342 (18)
O1	0.3684 (2)	0.29611 (7)	1.04053 (13)	0.0274 (4)
O2	0.4538 (2)	0.28777 (8)	0.69253 (14)	0.0240 (4)
H2A	0.562 (3)	0.2763 (11)	0.701 (2)	0.029*
H2B	0.406 (3)	0.2628 (10)	0.6508 (19)	0.029*
N1	0.3511 (2)	0.38231 (8)	0.52518 (15)	0.0193 (4)
N2	0.5890 (2)	0.42204 (8)	0.67754 (15)	0.0167 (4)
N3	0.4725 (2)	0.38883 (8)	0.88902 (15)	0.0159 (4)
N4	0.0713 (3)	0.32585 (10)	0.71154 (18)	0.0291 (5)
N5	0.1827 (3)	0.45968 (9)	0.73672 (16)	0.0216 (4)
C1	0.2350 (3)	0.35789 (11)	0.4504 (2)	0.0263 (6)
H1	0.1197	0.3424	0.4745	0.032*
C2	0.2752 (4)	0.35409 (12)	0.3394 (2)	0.0341 (6)
H2	0.1883	0.3371	0.2883	0.041*
C3	0.4436 (4)	0.37543 (13)	0.3045 (2)	0.0375 (7)
H3	0.4762	0.3724	0.2291	0.045*
C4	0.5648 (4)	0.40130 (12)	0.3805 (2)	0.0305 (6)
H4	0.6811	0.4167	0.3578	0.037*
C5	0.5147 (3)	0.40447 (10)	0.49019 (19)	0.0199 (5)
C6	0.6389 (3)	0.43017 (11)	0.57811 (19)	0.0206 (5)
C7	0.8112 (3)	0.46256 (13)	0.5449 (2)	0.0345 (7)
H7A	0.8537	0.4885	0.6054	0.052*
H7B	0.7838	0.4868	0.4791	0.052*
H7C	0.9089	0.4336	0.5283	0.052*
C8	0.6995 (3)	0.44329 (11)	0.77211 (19)	0.0217 (5)
H8A	0.7483	0.4837	0.7568	0.026*
H8B	0.8065	0.4163	0.7858	0.026*
C9	0.5774 (3)	0.44504 (10)	0.87324 (19)	0.0197 (5)
H9A	0.6566	0.4526	0.9396	0.024*
H9B	0.4882	0.4785	0.8656	0.024*
C10	0.6016 (3)	0.34062 (10)	0.92493 (19)	0.0209 (5)
H10A	0.6755	0.3543	0.9900	0.025*
H10B	0.6889	0.3319	0.8649	0.025*
C11	0.4980 (3)	0.28452 (11)	0.95414 (19)	0.0250 (6)
H11A	0.4299	0.2694	0.8880	0.030*
H11B	0.5877	0.2535	0.9788	0.030*
C12	0.2375 (3)	0.34069 (11)	1.0051 (2)	0.0245 (5)
H12A	0.1470	0.3480	1.0642	0.029*
H12B	0.1681	0.3265	0.9388	0.029*
C13	0.3372 (3)	0.39803 (10)	0.97860 (19)	0.0209 (5)
H13A	0.2450	0.4286	0.9555	0.025*
H13B	0.4037	0.4128	1.0456	0.025*
C14	−0.0226 (3)	0.28415 (11)	0.7138 (2)	0.0227 (5)
C15	0.1420 (3)	0.50395 (10)	0.78071 (18)	0.0158 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01428 (16)	0.01413 (18)	0.01570 (18)	−0.00171 (13)	0.00136 (12)	−0.00224 (14)
S1	0.0221 (3)	0.0171 (3)	0.0974 (7)	−0.0034 (3)	0.0035 (4)	−0.0039 (4)
S2	0.0328 (3)	0.0233 (4)	0.0442 (4)	0.0049 (3)	0.0016 (3)	−0.0134 (3)
O1	0.0381 (10)	0.0239 (10)	0.0206 (9)	0.0099 (8)	0.0089 (7)	0.0075 (7)
O2	0.0243 (9)	0.0218 (10)	0.0255 (10)	0.0047 (7)	−0.0053 (7)	−0.0081 (7)
N1	0.0207 (9)	0.0191 (11)	0.0179 (10)	0.0029 (8)	−0.0024 (8)	−0.0006 (8)
N2	0.0151 (8)	0.0190 (11)	0.0159 (10)	−0.0024 (7)	−0.0013 (7)	0.0015 (8)
N3	0.0214 (9)	0.0126 (10)	0.0137 (10)	0.0024 (7)	0.0012 (7)	−0.0006 (8)
N4	0.0211 (10)	0.0268 (13)	0.0394 (13)	−0.0052 (9)	0.0034 (9)	−0.0048 (10)
N5	0.0197 (9)	0.0214 (11)	0.0238 (11)	0.0021 (8)	−0.0002 (8)	−0.0008 (9)
C1	0.0291 (13)	0.0203 (14)	0.0291 (15)	0.0032 (10)	−0.0088 (11)	−0.0027 (11)
C2	0.0542 (17)	0.0258 (15)	0.0216 (15)	0.0046 (13)	−0.0162 (13)	−0.0041 (11)
C3	0.0604 (19)	0.0378 (17)	0.0142 (13)	0.0062 (14)	0.0003 (12)	0.0011 (12)
C4	0.0399 (15)	0.0308 (15)	0.0211 (14)	0.0036 (12)	0.0053 (11)	0.0064 (11)
C5	0.0235 (11)	0.0179 (13)	0.0182 (12)	0.0043 (9)	0.0006 (9)	0.0035 (10)
C6	0.0180 (10)	0.0217 (13)	0.0224 (13)	0.0016 (9)	0.0011 (9)	0.0076 (10)
C7	0.0211 (12)	0.0511 (19)	0.0314 (16)	−0.0071 (12)	0.0020 (11)	0.0174 (13)
C8	0.0202 (11)	0.0221 (13)	0.0225 (13)	−0.0067 (9)	−0.0040 (9)	0.0006 (10)
C9	0.0249 (11)	0.0155 (12)	0.0185 (13)	−0.0034 (9)	−0.0067 (9)	−0.0020 (9)
C10	0.0238 (11)	0.0203 (13)	0.0187 (13)	0.0043 (10)	−0.0001 (9)	−0.0017 (10)
C11	0.0370 (13)	0.0202 (14)	0.0181 (13)	0.0080 (11)	0.0065 (11)	0.0040 (10)
C12	0.0318 (13)	0.0247 (14)	0.0175 (13)	0.0078 (10)	0.0075 (10)	0.0062 (10)
C13	0.0302 (12)	0.0186 (13)	0.0140 (12)	0.0069 (10)	0.0038 (10)	0.0008 (9)
C14	0.0154 (10)	0.0222 (14)	0.0306 (14)	0.0023 (10)	0.0007 (10)	−0.0049 (11)
C15	0.0137 (10)	0.0179 (10)	0.0158 (12)	0.0012 (8)	−0.0006 (8)	0.0028 (8)

Geometric parameters (Å, º) top

Mn1—N1	2.2835 (19)	C3—C4	1.382 (4)
Mn1—N2	2.2115 (18)	C3—H3	0.9500
Mn1—N3	2.3891 (19)	C4—C5	1.386 (3)
Mn1—N4	2.137 (2)	C4—H4	0.9500
Mn1—N5	2.145 (2)	C5—C6	1.491 (3)
Mn1—O2	2.2117 (17)	C6—C7	1.497 (3)
S1—C14	1.631 (2)	C7—H7A	0.9800
S2—C15	1.618 (2)	C7—H7B	0.9800
O1—C12	1.432 (3)	C7—H7C	0.9800
O1—C11	1.438 (3)	C8—C9	1.521 (3)
O2—H2A	0.820 (16)	C8—H8A	0.9900
O2—H2B	0.824 (16)	C8—H8B	0.9900
N1—C1	1.336 (3)	C9—H9A	0.9900
N1—C5	1.352 (3)	C9—H9B	0.9900
N2—C6	1.276 (3)	C10—C11	1.507 (3)
N2—C8	1.460 (3)	C10—H10A	0.9900
N3—C9	1.482 (3)	C10—H10B	0.9900
N3—C10	1.483 (3)	C11—H11A	0.9900
N3—C13	1.486 (3)	C11—H11B	0.9900
N4—C14	1.153 (3)	C12—C13	1.509 (3)
N5—C15	1.166 (3)	C12—H12A	0.9900
C1—C2	1.384 (4)	C12—H12B	0.9900
C1—H1	0.9500	C13—H13A	0.9900
C2—C3	1.375 (4)	C13—H13B	0.9900
C2—H2	0.9500

N4—Mn1—N5	93.43 (8)	N2—C6—C5	116.3 (2)
N4—Mn1—N2	168.07 (8)	N2—C6—C7	124.9 (2)
N5—Mn1—N2	92.03 (7)	C5—C6—C7	118.8 (2)
N4—Mn1—O2	83.30 (7)	C6—C7—H7A	109.5
N5—Mn1—O2	176.33 (7)	C6—C7—H7B	109.5
N2—Mn1—O2	91.49 (7)	H7A—C7—H7B	109.5
N4—Mn1—N1	96.67 (8)	C6—C7—H7C	109.5
N5—Mn1—N1	97.88 (7)	H7A—C7—H7C	109.5
N2—Mn1—N1	72.05 (7)	H7B—C7—H7C	109.5
O2—Mn1—N1	84.17 (7)	N2—C8—C9	109.09 (17)
N4—Mn1—N3	115.48 (7)	N2—C8—H8A	109.9
N5—Mn1—N3	88.85 (7)	C9—C8—H8A	109.9
N2—Mn1—N3	75.21 (6)	N2—C8—H8B	109.9
O2—Mn1—N3	91.07 (6)	C9—C8—H8B	109.9
N1—Mn1—N3	146.75 (7)	H8A—C8—H8B	108.3
C12—O1—C11	109.80 (17)	N3—C9—C8	112.62 (18)
Mn1—O2—H2A	132.0 (19)	N3—C9—H9A	109.1
Mn1—O2—H2B	120.5 (19)	C8—C9—H9A	109.1
H2A—O2—H2B	104 (3)	N3—C9—H9B	109.1
C1—N1—C5	118.2 (2)	C8—C9—H9B	109.1
C1—N1—Mn1	125.76 (16)	H9A—C9—H9B	107.8
C5—N1—Mn1	115.18 (14)	N3—C10—C11	111.58 (19)
C6—N2—C8	122.36 (19)	N3—C10—H10A	109.3
C6—N2—Mn1	120.36 (15)	C11—C10—H10A	109.3
C8—N2—Mn1	117.27 (13)	N3—C10—H10B	109.3
C9—N3—C10	109.89 (17)	C11—C10—H10B	109.3
C9—N3—C13	108.54 (17)	H10A—C10—H10B	108.0
C10—N3—C13	107.53 (17)	O1—C11—C10	110.50 (19)
C9—N3—Mn1	101.71 (12)	O1—C11—H11A	109.6
C10—N3—Mn1	116.38 (13)	C10—C11—H11A	109.6
C13—N3—Mn1	112.49 (14)	O1—C11—H11B	109.6
C14—N4—Mn1	157.83 (19)	C10—C11—H11B	109.6
C15—N5—Mn1	157.80 (18)	H11A—C11—H11B	108.1
N1—C1—C2	123.0 (2)	O1—C12—C13	110.3 (2)
N1—C1—H1	118.5	O1—C12—H12A	109.6
C2—C1—H1	118.5	C13—C12—H12A	109.6
C3—C2—C1	118.6 (2)	O1—C12—H12B	109.6
C3—C2—H2	120.7	C13—C12—H12B	109.6
C1—C2—H2	120.7	H12A—C12—H12B	108.1
C2—C3—C4	119.2 (2)	N3—C13—C12	110.95 (18)
C2—C3—H3	120.4	N3—C13—H13A	109.4
C4—C3—H3	120.4	C12—C13—H13A	109.4
C3—C4—C5	119.2 (2)	N3—C13—H13B	109.4
C3—C4—H4	120.4	C12—C13—H13B	109.4
C5—C4—H4	120.4	H13A—C13—H13B	108.0
N1—C5—C4	121.8 (2)	N4—C14—S1	178.4 (2)
N1—C5—C6	115.45 (19)	N5—C15—S2	179.1 (2)
C4—C5—C6	122.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···S1ⁱ	0.82 (2)	2.38 (2)	3.1910 (18)	169 (2)
O2—H2B···O1ⁱⁱ	0.82 (2)	1.89 (2)	2.693 (2)	164 (3)
C11—H11A···O2	0.99	2.41	3.179 (3)	134
C12—H12A···S2ⁱⁱⁱ	0.99	2.82	3.674 (2)	145

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

Experimental details

Crystal data
Chemical formula	[Mn(NCS)₂(C₁₃H₁₉N₃O)(H₂O)]
M_r	422.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.1837 (13), 22.408 (4), 12.112 (2)
β (°)	91.149 (3)
V (Å³)	1949.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.19 × 0.16 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.846, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	11816, 4235, 3197
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.082, 1.01
No. of reflections	4235
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)	0.33, −0.46

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

Selected bond lengths (Å) top

Mn1—N1	2.2835 (19)	Mn1—N4	2.137 (2)
Mn1—N2	2.2115 (18)	Mn1—N5	2.145 (2)
Mn1—N3	2.3891 (19)	Mn1—O2	2.2117 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···S1ⁱ	0.820 (16)	2.382 (17)	3.1910 (18)	169 (2)
O2—H2B···O1ⁱⁱ	0.824 (16)	1.893 (18)	2.693 (2)	164 (3)
C11—H11A···O2	0.99	2.41	3.179 (3)	134
C12—H12A···S2ⁱⁱⁱ	0.99	2.82	3.674 (2)	145

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

Acknowledgements

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

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
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
Suleiman Gwaram, N., Ikmal Hisham, N. A., Khaledi, H. & Mohd Ali, H. (2011). Acta Cryst. E67, m108. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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