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Acta Cryst. (2007). E63, m2269-m2270    [ doi:10.1107/S160053680703718X ]

{2-[(2-Aminophenyl)iminomethyl]-4-bromophenolato-[kappa]3N,N',O}chloridobis(dimethyl sulfoxide-[kappa]S)ruthenium(II)

N. E. Eltayeb, S. G. Teoh, S. Chantrapromma, H.-K. Fun and K. Ibrahim

Abstract top

The title compound, [Ru(C13H10BrN2O)Cl(C2H6OS)2], shows a distorted octahedral RuII coordination with the N2O tridentate Schiff base ligand and one dimethyl sulfoxide (DMSO) molecule bonded in the equatorial plane, and the Cl and another DMSO ligand occupying the axial positions. In the crystal structure, molecules are linked by N-H...Cl and N-H...O hydrogen bonds into one-dimensional chains along the [100] direction. The crystal structure is further stabilized by weak C-H...O and C-H...Cl interactions. C-H...[pi] interactions are also observed in the crystal structure.

Comment top

Ruthenium chemistry is an interesting branch of chemistry due to the diverse properties of ruthenium and its photophysics and redox chemistry. Ruthenium complexes can be used as catalysts (Liu et al., 2007), luminescence materials (Kovacs et al., 2007), light emitting diodes (Lyons et al., 1998) and against Chagas' disease (Otero et al., 2003). Our current interest in the chemistry of ruthenium complexes is because of its properties as light emitting diodes. As a continuation of our research on Schiff base complexes (Eltayeb et al., 2007a; 2007b), we extend our studies to the ruthenium complexes with Schiff base ligands and herein the crystal structure of the title compound was reported.

The title complex molecule is characterized by a distort octahedral RuII coordination, with the N2O tridentate Schiff-base ligand and one S-DMSO in the basal plane and another S-DMSO and Cl occupied in the axial positions (Fig. 1). The Ru(II) is in the same plane with the N1/N2/O1/S1 basal plane. The cyclic skeleton of the tridentate Schiff-base ligand is not planar as indicated by the dihedral angle between the two benzene rings of 14.5 (2)°. Bond lengths and angles observed in the structure are in normal ranges (Allen et al., 1987). The bond lengths and angles of the Schiff base ligand are comparable with the related structures (Eltayeb et al., 2007a; 2007b). The Ru—S bond distances [Ru1—S1 = 2.2511 (9)Å and Ru1—S2 = 2.2206 (9) Å] are typical for the complexes of ruthenium with S-coordinated DMSO in the coordination sphere (Calligaris, 2004; Otero et al., 2003). The Cl atom is pushed toward the Schiff-base ligand side of the complex with a S2—Ru1—Cl1 bond angle of 172.75 (3)° for steric reason. The endocyclic N1—Ru1—N2 and N2—Ru1—O1 bond angles are 81.38 (12)° and 93.33 (11)° because of the chelate nature of the ligand.

In the crystal structure of the title compound (Fig. 2), the molecules are connected by N—H···Cl and N—H···O hydrogen bonds into 1-D chains along the [1 0 0] direction. The crystal is stabilized by intermolecular N—H···Cl and N—H···O hydrogen bonds together with weak C—H···O and C—H···Cl interactions (Table 1). C—H···π interactions are also observed (Table 1); Cg1 and Cg2 are the centroids of C1–C6 and C8–C13 benzene rings, respectively.

Related literature top

For related structures, see, for example: Calligaris (2004); Otero et al. (2003); Rusanova et al. (2006). For related literature on Schiff base coordination complexes and applications of RuII complexes, see: Eltayeb et al. (2007a,b); Kovacs et al. (2007 or 2006?); Liu et al. (2007); Lyons et al. (1998); Otero et al. (2003). Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

For bond length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by adding 5-bromo-2-hydroxybenzaldehyde (0.402 g, 2 mmol) into a solution of o-phenylenediamine (0.108 g, 1 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. Dichlorotetrakis(dimethylsulfoxide)ruthenium(II) (0.484 g, 1 mmol) in ethanol (20 ml) was then added. The mixture was refluxed with heating and stirring for two hours. A dark brown-red solution was obtained, wherein brown single crystals suitable for x-ray structure determination were formed after one week of slow evaporation of the solvent.

Refinement top

H atoms of the NH2 group were located from the difference map and isotropically refined. The remainning H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual peak is located 0.82 Å from S1 and the deepest hole is located 0.77 Å from Ru1.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the c axis. Hydrogen bond were drawn as dash lines.
{2-[(2-Aminophenyl)iminomethyl]-4-bromophenolato- κ3N,N',O}chloridobis(dimethyl sulfoxide-κS)ruthenium(II) top
Crystal data top
[Ru(C13H10BrN2O)Cl(C2H6OS)2]Z = 2
Mr = 582.92F000 = 580
Triclinic, P1Dx = 1.889 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.1302 (3) ÅCell parameters from 5964 reflections
b = 12.0908 (4) Åθ = 2.7–30.0º
c = 12.2445 (6) ŵ = 3.07 mm−1
α = 115.774 (3)ºT = 100.0 (1) K
β = 101.712 (3)ºBlock, black
γ = 98.135 (2)º0.13 × 0.11 × 0.10 mm
V = 1024.67 (8) Å3
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		5964 independent reflections
Radiation source: fine-focus sealed tube4532 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
Detector resolution: 8.33 pixels mm-1θmax = 30.0º
T = 100.0(1) Kθmin = 2.7º
ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −16→16
Tmin = 0.686, Tmax = 0.755l = −17→17
19338 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.105  w = 1/[σ2(Fo2) + (0.048P)2 + 0.8835P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5964 reflectionsΔρmax = 1.25 e Å−3
256 parametersΔρmin = −0.96 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ru(C13H10BrN2O)Cl(C2H6OS)2]γ = 98.135 (2)º
Mr = 582.92V = 1024.67 (8) Å3
Triclinic, P1Z = 2
a = 8.1302 (3) ÅMo Kα
b = 12.0908 (4) ŵ = 3.07 mm−1
c = 12.2445 (6) ÅT = 100.0 (1) K
α = 115.774 (3)º0.13 × 0.11 × 0.10 mm
β = 101.712 (3)º
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		5964 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4532 reflections with I > 2σ(I)
Tmin = 0.686, Tmax = 0.755Rint = 0.039
19338 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041256 parameters
wR(F2) = 0.105H atoms treated by a mixture of
independent and constrained refinement
S = 1.07Δρmax = 1.25 e Å−3
5964 reflectionsΔρmin = −0.96 e Å−3
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
Ru10.79226 (3)0.36415 (3)0.12373 (3)0.01612 (9)
Br11.39210 (5)0.12129 (4)0.45490 (4)0.03040 (12)
Cl11.03365 (11)0.35010 (9)0.03345 (9)0.02261 (19)
S10.59540 (11)0.26471 (9)−0.06999 (9)0.0213 (2)
S20.59443 (11)0.37706 (9)0.22689 (9)0.02027 (19)
O10.8085 (3)0.1943 (2)0.1222 (2)0.0208 (5)
O20.4362 (3)0.3112 (3)−0.0816 (3)0.0273 (6)
O30.6586 (3)0.4040 (3)0.3597 (3)0.0292 (6)
N10.8072 (4)0.5441 (3)0.1349 (3)0.0183 (6)
N20.9799 (4)0.4710 (3)0.2943 (3)0.0175 (6)
C10.9182 (4)0.6432 (4)0.2601 (4)0.0203 (7)
C20.9370 (5)0.7702 (4)0.2943 (4)0.0230 (8)
H2A0.87330.79400.23980.028*
C31.0502 (5)0.8609 (4)0.4092 (4)0.0278 (9)
H3A1.06550.94660.43200.033*
C41.1415 (5)0.8257 (4)0.4911 (4)0.0277 (9)
H4A1.21660.88820.56940.033*
C51.1232 (5)0.6986 (4)0.4588 (4)0.0223 (8)
H5A1.18570.67580.51470.027*
C61.0095 (4)0.6048 (3)0.3406 (3)0.0199 (7)
C71.0733 (5)0.4251 (4)0.3538 (4)0.0211 (8)
H7A1.15490.48280.43130.025*
C81.0621 (5)0.2923 (4)0.3104 (3)0.0216 (8)
C91.1924 (5)0.2684 (4)0.3865 (4)0.0213 (8)
H9A1.27080.33620.45990.026*
C101.2053 (5)0.1465 (4)0.3538 (4)0.0251 (8)
C111.0886 (5)0.0434 (4)0.2437 (4)0.0264 (8)
H11A1.0990−0.03880.22080.032*
C120.9588 (5)0.0641 (4)0.1699 (4)0.0241 (8)
H12A0.8812−0.00550.09760.029*
C130.9381 (4)0.1883 (4)0.1995 (3)0.0210 (8)
C140.4181 (5)0.2370 (4)0.1500 (4)0.0286 (9)
H14A0.34300.24440.20270.043*
H14B0.46300.16420.13620.043*
H14C0.35360.22700.07000.043*
C150.4777 (5)0.4921 (4)0.2296 (4)0.0278 (9)
H15A0.38810.48740.26900.042*
H15B0.42600.47510.14420.042*
H15C0.55620.57560.27690.042*
C160.6823 (5)0.2727 (4)−0.1903 (4)0.0294 (9)
H16A0.59050.2366−0.26870.044*
H16B0.76910.2260−0.20170.044*
H16C0.73390.3600−0.16490.044*
C170.5297 (5)0.0960 (4)−0.1386 (4)0.0340 (10)
H17A0.46200.0601−0.22580.051*
H17B0.46080.0732−0.09290.051*
H17C0.63080.0638−0.13420.051*
H1N10.861 (5)0.552 (4)0.076 (4)0.023 (11)*
H2N10.701 (6)0.560 (4)0.125 (4)0.039 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01129 (13)0.02104 (16)0.01781 (15)0.00654 (11)0.00418 (10)0.01019 (12)
Br10.0246 (2)0.0381 (2)0.0317 (2)0.01639 (18)0.00366 (17)0.0190 (2)
Cl10.0189 (4)0.0307 (5)0.0251 (5)0.0111 (4)0.0107 (3)0.0160 (4)
S10.0160 (4)0.0264 (5)0.0195 (5)0.0088 (4)0.0024 (3)0.0095 (4)
S20.0150 (4)0.0280 (5)0.0217 (5)0.0085 (4)0.0067 (3)0.0138 (4)
O10.0145 (11)0.0244 (14)0.0230 (14)0.0068 (10)0.0028 (10)0.0115 (11)
O20.0223 (13)0.0395 (16)0.0247 (15)0.0195 (12)0.0052 (11)0.0167 (13)
O30.0235 (13)0.0435 (17)0.0223 (14)0.0120 (13)0.0074 (11)0.0160 (13)
N10.0155 (14)0.0196 (16)0.0239 (17)0.0072 (12)0.0053 (12)0.0134 (14)
N20.0149 (13)0.0234 (16)0.0170 (15)0.0071 (12)0.0069 (11)0.0104 (13)
C10.0129 (15)0.0246 (19)0.0223 (19)0.0083 (14)0.0071 (13)0.0086 (16)
C20.0205 (17)0.025 (2)0.032 (2)0.0090 (15)0.0131 (16)0.0182 (17)
C30.0250 (19)0.031 (2)0.026 (2)0.0098 (17)0.0118 (16)0.0094 (18)
C40.0216 (18)0.029 (2)0.023 (2)0.0048 (16)0.0078 (15)0.0044 (17)
C50.0187 (17)0.026 (2)0.0219 (19)0.0072 (15)0.0067 (14)0.0108 (16)
C60.0155 (16)0.0236 (19)0.0204 (19)0.0093 (14)0.0080 (14)0.0080 (16)
C70.0177 (16)0.026 (2)0.0218 (19)0.0079 (15)0.0065 (14)0.0128 (16)
C80.0190 (17)0.033 (2)0.0187 (18)0.0114 (15)0.0083 (14)0.0143 (17)
C90.0190 (17)0.027 (2)0.0199 (19)0.0098 (15)0.0054 (14)0.0119 (16)
C100.0187 (17)0.037 (2)0.026 (2)0.0132 (17)0.0067 (15)0.0187 (19)
C110.0230 (18)0.027 (2)0.032 (2)0.0107 (16)0.0084 (16)0.0154 (18)
C120.0201 (17)0.026 (2)0.028 (2)0.0056 (15)0.0051 (15)0.0149 (17)
C130.0148 (16)0.031 (2)0.0200 (19)0.0082 (15)0.0063 (14)0.0135 (17)
C140.0239 (19)0.030 (2)0.031 (2)0.0014 (16)0.0107 (17)0.0144 (18)
C150.0231 (19)0.035 (2)0.030 (2)0.0150 (17)0.0124 (16)0.0156 (19)
C160.029 (2)0.042 (2)0.024 (2)0.0126 (18)0.0112 (17)0.0184 (19)
C170.029 (2)0.034 (2)0.028 (2)0.0077 (18)0.0037 (18)0.0073 (19)
Geometric parameters (Å, °) top
Ru1—N22.040 (3)C4—H4A0.9300
Ru1—O12.069 (2)C5—C61.402 (5)
Ru1—N12.104 (3)C5—H5A0.9300
Ru1—S22.2206 (9)C7—C81.437 (5)
Ru1—S12.2511 (9)C7—H7A0.9300
Ru1—Cl12.4319 (9)C8—C91.412 (5)
Br1—C101.905 (3)C8—C131.429 (5)
S1—O21.488 (3)C9—C101.375 (5)
S1—C171.781 (4)C9—H9A0.9300
S1—C161.790 (4)C10—C111.398 (5)
S2—O31.474 (3)C11—C121.370 (5)
S2—C151.784 (4)C11—H11A0.9300
S2—C141.786 (4)C12—C131.428 (5)
O1—C131.298 (4)C12—H12A0.9300
N1—C11.461 (5)C14—H14A0.9600
N1—H1N10.95 (4)C14—H14B0.9600
N1—H2N10.90 (5)C14—H14C0.9600
N2—C71.289 (4)C15—H15A0.9600
N2—C61.426 (5)C15—H15B0.9600
C1—C21.381 (5)C15—H15C0.9600
C1—C61.392 (5)C16—H16A0.9600
C2—C31.370 (5)C16—H16B0.9600
C2—H2A0.9300C16—H16C0.9600
C3—C41.377 (6)C17—H17A0.9600
C3—H3A0.9300C17—H17B0.9600
C4—C51.387 (5)C17—H17C0.9600
N2—Ru1—O193.33 (11)C4—C5—H5A120.4
N2—Ru1—N181.38 (12)C6—C5—H5A120.4
O1—Ru1—N1173.35 (10)C1—C6—C5118.5 (3)
N2—Ru1—S288.91 (8)C1—C6—N2116.3 (3)
O1—Ru1—S289.22 (7)C5—C6—N2125.2 (3)
N1—Ru1—S294.67 (9)N2—C7—C8125.5 (3)
N2—Ru1—S1173.20 (9)N2—C7—H7A117.2
O1—Ru1—S192.61 (7)C8—C7—H7A117.2
N1—Ru1—S192.46 (9)C9—C8—C13119.7 (3)
S2—Ru1—S194.48 (3)C9—C8—C7114.0 (3)
N2—Ru1—Cl185.04 (8)C13—C8—C7126.3 (3)
O1—Ru1—Cl187.14 (7)C10—C9—C8121.1 (4)
N1—Ru1—Cl188.38 (9)C10—C9—H9A119.5
S2—Ru1—Cl1172.75 (3)C8—C9—H9A119.5
S1—Ru1—Cl191.95 (3)C9—C10—C11120.2 (3)
O2—S1—C17108.13 (18)C9—C10—Br1119.0 (3)
O2—S1—C16105.03 (18)C11—C10—Br1120.6 (3)
C17—S1—C1697.9 (2)C12—C11—C10119.7 (4)
O2—S1—Ru1116.15 (12)C12—C11—H11A120.1
C17—S1—Ru1114.69 (15)C10—C11—H11A120.1
C16—S1—Ru1113.08 (14)C11—C12—C13122.6 (4)
O3—S2—C15106.04 (18)C11—C12—H12A118.7
O3—S2—C14106.19 (18)C13—C12—H12A118.7
C15—S2—C1499.9 (2)O1—C13—C12116.3 (3)
O3—S2—Ru1116.07 (11)O1—C13—C8127.1 (3)
C15—S2—Ru1113.99 (14)C12—C13—C8116.6 (3)
C14—S2—Ru1113.06 (14)S2—C14—H14A109.5
C13—O1—Ru1121.4 (2)S2—C14—H14B109.5
C1—N1—Ru1109.8 (2)H14A—C14—H14B109.5
C1—N1—H1N1106 (2)S2—C14—H14C109.5
Ru1—N1—H1N1111 (2)H14A—C14—H14C109.5
C1—N1—H2N1107 (3)H14B—C14—H14C109.5
Ru1—N1—H2N1111 (3)S2—C15—H15A109.5
H1N1—N1—H2N1112 (4)S2—C15—H15B109.5
C7—N2—C6121.3 (3)H15A—C15—H15B109.5
C7—N2—Ru1124.5 (3)S2—C15—H15C109.5
C6—N2—Ru1114.0 (2)H15A—C15—H15C109.5
C2—C1—C6121.6 (3)H15B—C15—H15C109.5
C2—C1—N1120.7 (3)S1—C16—H16A109.5
C6—C1—N1117.7 (3)S1—C16—H16B109.5
C3—C2—C1119.4 (4)H16A—C16—H16B109.5
C3—C2—H2A120.3S1—C16—H16C109.5
C1—C2—H2A120.3H16A—C16—H16C109.5
C2—C3—C4120.2 (4)H16B—C16—H16C109.5
C2—C3—H3A119.9S1—C17—H17A109.5
C4—C3—H3A119.9S1—C17—H17B109.5
C3—C4—C5121.1 (4)H17A—C17—H17B109.5
C3—C4—H4A119.4S1—C17—H17C109.5
C5—C4—H4A119.4H17A—C17—H17C109.5
C4—C5—C6119.2 (4)H17B—C17—H17C109.5
O1—Ru1—S1—O2129.94 (15)S2—Ru1—N2—C6−87.7 (2)
N1—Ru1—S1—O2−54.37 (16)Cl1—Ru1—N2—C696.3 (2)
S2—Ru1—S1—O240.52 (14)Ru1—N1—C1—C2−174.7 (3)
Cl1—Ru1—S1—O2−142.83 (14)Ru1—N1—C1—C68.1 (4)
O1—Ru1—S1—C172.55 (18)C6—C1—C2—C31.1 (6)
N1—Ru1—S1—C17178.24 (19)N1—C1—C2—C3−176.0 (3)
S2—Ru1—S1—C17−86.87 (17)C1—C2—C3—C4−1.5 (6)
Cl1—Ru1—S1—C1789.78 (17)C2—C3—C4—C51.0 (6)
O1—Ru1—S1—C16−108.52 (17)C3—C4—C5—C6−0.1 (6)
N1—Ru1—S1—C1667.17 (18)C2—C1—C6—C5−0.3 (5)
S2—Ru1—S1—C16162.06 (16)N1—C1—C6—C5176.9 (3)
Cl1—Ru1—S1—C16−21.29 (16)C2—C1—C6—N2−179.6 (3)
N2—Ru1—S2—O3−22.80 (16)N1—C1—C6—N2−2.4 (5)
O1—Ru1—S2—O370.55 (15)C4—C5—C6—C1−0.2 (5)
N1—Ru1—S2—O3−104.06 (16)C4—C5—C6—N2179.0 (3)
S1—Ru1—S2—O3163.10 (14)C7—N2—C6—C1171.1 (3)
N2—Ru1—S2—C15100.87 (17)Ru1—N2—C6—C1−4.9 (4)
O1—Ru1—S2—C15−165.78 (17)C7—N2—C6—C5−8.2 (5)
N1—Ru1—S2—C1519.61 (17)Ru1—N2—C6—C5175.8 (3)
S1—Ru1—S2—C15−73.23 (15)C6—N2—C7—C8−175.3 (3)
N2—Ru1—S2—C14−145.87 (17)Ru1—N2—C7—C80.3 (5)
O1—Ru1—S2—C14−52.52 (17)N2—C7—C8—C9173.2 (3)
N1—Ru1—S2—C14132.87 (17)N2—C7—C8—C13−4.9 (6)
S1—Ru1—S2—C1440.03 (16)C13—C8—C9—C101.8 (6)
N2—Ru1—O1—C13−14.2 (3)C7—C8—C9—C10−176.4 (3)
S2—Ru1—O1—C13−103.1 (3)C8—C9—C10—C110.0 (6)
S1—Ru1—O1—C13162.5 (3)C8—C9—C10—Br1176.4 (3)
Cl1—Ru1—O1—C1370.6 (3)C9—C10—C11—C12−1.4 (6)
N2—Ru1—N1—C1−8.0 (2)Br1—C10—C11—C12−177.7 (3)
S2—Ru1—N1—C180.1 (2)C10—C11—C12—C130.9 (6)
S1—Ru1—N1—C1174.9 (2)Ru1—O1—C13—C12−165.0 (2)
Cl1—Ru1—N1—C1−93.3 (2)Ru1—O1—C13—C814.8 (5)
O1—Ru1—N2—C77.3 (3)C11—C12—C13—O1−179.3 (4)
N1—Ru1—N2—C7−168.7 (3)C11—C12—C13—C80.9 (6)
S2—Ru1—N2—C796.4 (3)C9—C8—C13—O1178.0 (3)
Cl1—Ru1—N2—C7−79.6 (3)C7—C8—C13—O1−4.0 (6)
O1—Ru1—N2—C6−176.8 (2)C9—C8—C13—C12−2.2 (5)
N1—Ru1—N2—C67.2 (2)C7—C8—C13—C12175.8 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···Cl1i0.95 (5)2.34 (5)3.235 (4)157 (4)
N1—H2N1···O2ii0.91 (5)2.22 (5)2.975 (5)141 (4)
C2—H2A···O2ii0.932.583.267 (5)131
C5—H5A···O3iii0.932.403.323 (6)174
C7—H7A···O3iii0.932.353.263 (5)168
C16—H16B···Cl10.962.833.222 (4)106
C14—H14A···Cg2iv0.962.733.634 (5)157
C16—H16B···Cg1i0.963.093.561 (5)112
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1; (iv) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···Cl1i0.95 (5)2.34 (5)3.235 (4)157 (4)
N1—H2N1···O2ii0.91 (5)2.22 (5)2.975 (5)141 (4)
C2—H2A···O2ii0.932.583.267 (5)131
C5—H5A···O3iii0.932.403.323 (6)174
C7—H7A···O3iii0.932.353.263 (5)168
C16—H16B···Cl10.962.833.222 (4)106
C14—H14A···Cg2iv0.962.733.634 (5)157
C16—H16B···Cg1i0.963.093.561 (5)112
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1; (iv) x−1, y, z.
Acknowledgements top

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation, Malaysia (MOSTI), and Universiti Sains Malaysia for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

references
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