Bis{benzyl 3-[(1H-indol-3-yl)methyl­idene]dithio­carbazato-κ2N3,S}palladium(II) pyridine disolvate

Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811001991

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m230

doi:10.1107/S1600536811001991

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Bis{benzyl 3-[(1H-indol-3-yl)methylidene]dithiocarbazato-κ²N³,S}palladium(II) pyridine disolvate

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 10 January 2011; accepted 13 January 2011; online 22 January 2011)

The Pd^II ion in the title compound, [Pd(C₁₇H₁₄N₃S₂)₂]·2C₅H₅N, is located on an inversion center and is four-coordinated by two of the deprotonated N,S-bidentate Schiff base ligands in a square-planar geometry. The dihedral angle between the aromatic ring planes within the ligand is 71.12 (9)°. The indole NH groups are bonded to the pyridine solvent molecules via an N—H⋯N interaction. The crystal structure is consolidated by intermolecular C—H⋯S interactions.

Related literature

For the analogous DMF disolvate Pd^II complex, see: Khaledi & Mohd Ali (2011 ). For a discussion of the coordination chemistry of indole-based S-benzyldithiocarbazones, see: Khaledi et al. (2011 ).

Experimental

Crystal data

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₅H₅N
M_r = 913.46
Triclinic, $[P \overline 1]$
a = 9.9688 (2) Å
b = 10.5041 (2) Å
c = 10.9491 (2) Å
α = 62.534 (2)°
β = 78.494 (2)°
γ = 78.985 (2)°
V = 990.35 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.10 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.931, T_max = 0.965
8128 measured reflections
3879 independent reflections
3045 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.070
S = 0.99
3879 reflections
262 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4	0.86 (2)	1.96 (2)	2.808 (4)	171 (3)
C9—H9⋯S1ⁱ	0.95	2.58	3.267 (3)	130
Symmetry code: (i) -x, -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/S1600536811001991/pv2380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001991/pv2380Isup2.hkl

checkCIF report

Comment top

The crystal of the title compound was obtained from a pyridine solution of the Pd^II complex of indole-3-carbaldehyde S-benzyldithiocarbazone. Upon deprotonation, the Schiff base chelates the Pd^II ion in an N,S-bidentate bonding mode to form a five-membered ring with the metal center. The Pd^II ion, located on an inversion center, is four-coordinated by two of the Schiff base ligands in a square-planar geometry. The pyridine solvent molecules remain uncoordinated to the metal ion and are hydrogen bonded to indole NH groups. This is similar to what was observed in the structure of the analogous DMF solvate Pd^II complex (Khaledi & Mohd Ali, 2011). In contrast, the cadmium(II) complex of the Schiff base ligand in a pyridine solution gave an octahedral complex wherein two trans-pyridine molecules are coordinated to the metal center (Khaledi et al., 2011). In the present structure, the aromatic ring planes within the ligand make a dihedral angle of 71.12 (9)°. The pyridine solvent ring is nearly coplanar with the indole ring, the dihedral angle between them being 11.39 (19)°. The structure is further consolidated by intramolecular interactions of the types C—H···S and C—H···N (Table 1).

Related literature top

For the analogous DMF disolvate Pd^II complex, see: Khaledi & Mohd Ali (2011). For a discussion of the coordination chemistry of indole-based S-benzyldithiocarbazones, see: Khaledi et al. (2011).

Experimental top

The Schiff base ligand was prepared as reported previously (Khaledi et al., 2011). A solution of palladium(II) acetate (0.224 g, 1 mmol) in ethanol (30 ml) was added to an ethanolic solution (30 ml) of the ligand (0.65 g, 2 mmol) containing a few drops of triethylamine. The mixture was refluxed for an hour, then cooled to room temperature. The resulting brown solid was filtered, washed with cold ethanol and dried over siliga-gel. The crystals of the title compound were obtained by slow evaporation of a solution of the solid in pyridine.

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 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabeled atoms are related to the labeled atoms by symmetry operation: -x, -y, -z.

Bis{benzyl 3-[(1H-indol-3-yl)methylidene]dithiocarbazato- κ²N³,S}palladium(II) pyridine disolvate top

Crystal data top

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₅H₅N	Z = 1
M_r = 913.46	F(000) = 468
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9688 (2) Å	Cell parameters from 2496 reflections
b = 10.5041 (2) Å	θ = 2.2–27.4°
c = 10.9491 (2) Å	µ = 0.72 mm⁻¹
α = 62.534 (2)°	T = 100 K
β = 78.494 (2)°	Block, red
γ = 78.985 (2)°	0.10 × 0.07 × 0.05 mm
V = 990.35 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3879 independent reflections
Radiation source: fine-focus sealed tube	3045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.931, T_max = 0.965	k = −12→12
8128 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0263P)²] where P = (F_o² + 2F_c²)/3
3879 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.73 e Å⁻³
1 restraint	Δρ_min = −1.03 e Å⁻³

Crystal data top

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₅H₅N	γ = 78.985 (2)°
M_r = 913.46	V = 990.35 (3) Å³
Triclinic, P1	Z = 1
a = 9.9688 (2) Å	Mo Kα radiation
b = 10.5041 (2) Å	µ = 0.72 mm⁻¹
c = 10.9491 (2) Å	T = 100 K
α = 62.534 (2)°	0.10 × 0.07 × 0.05 mm
β = 78.494 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3879 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3045 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.965	R_int = 0.041
8128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.73 e Å⁻³
3879 reflections	Δρ_min = −1.03 e Å⁻³
262 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
Pd1	0.0000	0.0000	0.0000	0.01415 (11)
S1	0.22662 (8)	−0.07299 (8)	0.03590 (8)	0.01946 (19)
S2	0.39814 (8)	0.01851 (8)	0.15858 (8)	0.01993 (19)
N1	−0.0326 (3)	0.4905 (3)	0.2098 (3)	0.0209 (6)
H1N	0.014 (3)	0.528 (3)	0.240 (3)	0.025*
N2	0.0161 (3)	0.1372 (2)	0.0784 (2)	0.0161 (6)
N3	0.1382 (3)	0.1317 (2)	0.1281 (2)	0.0168 (6)
C1	0.0172 (3)	0.3767 (3)	0.1816 (3)	0.0211 (7)
H1	0.1081	0.3286	0.1913	0.025*
C2	−0.0838 (3)	0.3404 (3)	0.1364 (3)	0.0175 (7)
C3	−0.2052 (3)	0.4404 (3)	0.1403 (3)	0.0175 (7)
C4	−0.3413 (3)	0.4581 (3)	0.1129 (3)	0.0207 (7)
H4	−0.3696	0.3974	0.0822	0.025*
C5	−0.4324 (3)	0.5660 (3)	0.1317 (3)	0.0247 (8)
H5	−0.5249	0.5785	0.1146	0.030*
C6	−0.3925 (4)	0.6577 (3)	0.1754 (3)	0.0257 (8)
H6	−0.4580	0.7315	0.1863	0.031*
C7	−0.2600 (3)	0.6428 (3)	0.2026 (3)	0.0236 (8)
H7	−0.2324	0.7052	0.2317	0.028*
C8	−0.1682 (3)	0.5327 (3)	0.1860 (3)	0.0185 (7)
C9	−0.0809 (3)	0.2353 (3)	0.0870 (3)	0.0161 (7)
H9	−0.1638	0.2379	0.0551	0.019*
C10	0.2357 (3)	0.0394 (3)	0.1092 (3)	0.0155 (7)
C11	0.3916 (3)	0.1657 (3)	0.2031 (3)	0.0192 (7)
H11A	0.4837	0.2004	0.1736	0.023*
H11B	0.3258	0.2461	0.1484	0.023*
C12	0.3507 (3)	0.1328 (3)	0.3543 (3)	0.0180 (7)
C13	0.2418 (3)	0.0539 (3)	0.4334 (3)	0.0243 (7)
H13	0.1898	0.0208	0.3920	0.029*
C14	0.2083 (4)	0.0229 (3)	0.5724 (3)	0.0283 (8)
H14	0.1344	−0.0324	0.6260	0.034*
C15	0.2820 (4)	0.0720 (3)	0.6337 (3)	0.0289 (8)
H15	0.2590	0.0507	0.7291	0.035*
C16	0.3883 (4)	0.1516 (3)	0.5552 (3)	0.0265 (8)
H16	0.4383	0.1868	0.5964	0.032*
C17	0.4238 (3)	0.1814 (3)	0.4174 (3)	0.0209 (7)
H17	0.4988	0.2356	0.3650	0.025*
N4	0.1071 (3)	0.5947 (3)	0.3379 (3)	0.0247 (6)
C18	0.0482 (4)	0.6915 (3)	0.3856 (3)	0.0293 (8)
H18	−0.0442	0.7315	0.3704	0.035*
C19	0.1138 (4)	0.7360 (4)	0.4550 (3)	0.0322 (8)
H19	0.0671	0.8044	0.4875	0.039*
C20	0.2470 (4)	0.6811 (4)	0.4771 (4)	0.0392 (10)
H20	0.2951	0.7107	0.5245	0.047*
C21	0.3098 (4)	0.5814 (4)	0.4286 (4)	0.0435 (10)
H21	0.4026	0.5412	0.4416	0.052*
C22	0.2362 (4)	0.5409 (4)	0.3610 (3)	0.0327 (9)
H22	0.2799	0.4710	0.3293	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0175 (2)	0.01085 (18)	0.0166 (2)	−0.00293 (15)	−0.00176 (15)	−0.00774 (15)
S1	0.0206 (5)	0.0190 (4)	0.0251 (4)	−0.0007 (4)	−0.0042 (4)	−0.0151 (4)
S2	0.0200 (5)	0.0204 (4)	0.0249 (4)	0.0001 (4)	−0.0052 (4)	−0.0147 (4)
N1	0.0240 (17)	0.0187 (14)	0.0272 (15)	−0.0053 (12)	−0.0004 (12)	−0.0160 (12)
N2	0.0220 (15)	0.0108 (12)	0.0192 (13)	−0.0021 (11)	−0.0027 (11)	−0.0094 (10)
N3	0.0201 (15)	0.0144 (13)	0.0184 (13)	−0.0034 (12)	−0.0033 (11)	−0.0084 (11)
C1	0.0260 (19)	0.0155 (15)	0.0219 (17)	−0.0009 (14)	−0.0011 (14)	−0.0096 (13)
C2	0.0228 (18)	0.0120 (14)	0.0159 (15)	−0.0032 (13)	0.0021 (13)	−0.0060 (12)
C3	0.0207 (18)	0.0128 (15)	0.0157 (16)	−0.0033 (14)	0.0030 (13)	−0.0050 (12)
C4	0.026 (2)	0.0179 (16)	0.0185 (16)	−0.0060 (14)	−0.0002 (14)	−0.0081 (13)
C5	0.0251 (19)	0.0237 (17)	0.0209 (17)	0.0025 (15)	−0.0028 (14)	−0.0082 (14)
C6	0.032 (2)	0.0178 (16)	0.0204 (17)	0.0060 (15)	0.0017 (15)	−0.0080 (13)
C7	0.034 (2)	0.0141 (15)	0.0213 (17)	0.0000 (15)	0.0000 (15)	−0.0093 (13)
C8	0.0207 (18)	0.0165 (15)	0.0173 (16)	−0.0043 (14)	0.0028 (13)	−0.0079 (13)
C9	0.0170 (17)	0.0153 (15)	0.0149 (15)	−0.0052 (13)	−0.0009 (13)	−0.0051 (12)
C10	0.0210 (18)	0.0133 (14)	0.0115 (15)	−0.0045 (13)	−0.0006 (13)	−0.0046 (12)
C11	0.0186 (18)	0.0183 (15)	0.0240 (17)	−0.0048 (14)	−0.0022 (14)	−0.0111 (13)
C12	0.0211 (18)	0.0139 (15)	0.0189 (16)	0.0027 (13)	−0.0056 (13)	−0.0077 (13)
C13	0.0253 (19)	0.0274 (17)	0.0255 (18)	−0.0069 (15)	−0.0023 (15)	−0.0149 (15)
C14	0.030 (2)	0.0265 (17)	0.0221 (17)	−0.0056 (16)	0.0026 (14)	−0.0066 (14)
C15	0.039 (2)	0.0242 (17)	0.0201 (18)	0.0099 (17)	−0.0075 (16)	−0.0106 (15)
C16	0.035 (2)	0.0217 (17)	0.0277 (18)	0.0053 (16)	−0.0130 (16)	−0.0149 (15)
C17	0.0237 (19)	0.0162 (15)	0.0246 (17)	−0.0011 (14)	−0.0053 (14)	−0.0102 (13)
N4	0.0237 (16)	0.0202 (14)	0.0313 (16)	−0.0052 (13)	−0.0042 (13)	−0.0110 (12)
C18	0.025 (2)	0.0247 (18)	0.041 (2)	−0.0061 (16)	0.0012 (16)	−0.0175 (16)
C19	0.038 (2)	0.032 (2)	0.033 (2)	−0.0160 (18)	0.0082 (17)	−0.0209 (16)
C20	0.047 (3)	0.051 (2)	0.025 (2)	−0.027 (2)	−0.0019 (18)	−0.0140 (18)
C21	0.030 (2)	0.057 (3)	0.034 (2)	0.001 (2)	−0.0108 (18)	−0.011 (2)
C22	0.034 (2)	0.0276 (19)	0.031 (2)	0.0034 (17)	−0.0009 (17)	−0.0120 (16)

Geometric parameters (Å, º) top

Pd1—N2ⁱ	2.031 (2)	C9—H9	0.9500
Pd1—N2	2.031 (2)	C11—C12	1.510 (4)
Pd1—S1ⁱ	2.2936 (8)	C11—H11A	0.9900
Pd1—S1	2.2936 (8)	C11—H11B	0.9900
S1—C10	1.729 (3)	C12—C13	1.387 (4)
S2—C10	1.751 (3)	C12—C17	1.393 (4)
S2—C11	1.810 (3)	C13—C14	1.384 (4)
N1—C1	1.350 (4)	C13—H13	0.9500
N1—C8	1.377 (4)	C14—C15	1.384 (5)
N1—H1N	0.857 (18)	C14—H14	0.9500
N2—C9	1.296 (3)	C15—C16	1.369 (5)
N2—N3	1.411 (3)	C15—H15	0.9500
N3—C10	1.294 (3)	C16—C17	1.376 (4)
C1—C2	1.387 (4)	C16—H16	0.9500
C1—H1	0.9500	C17—H17	0.9500
C2—C9	1.430 (4)	N4—C22	1.326 (4)
C2—C3	1.450 (4)	N4—C18	1.339 (4)
C3—C8	1.408 (4)	C18—C19	1.365 (5)
C3—C4	1.408 (4)	C18—H18	0.9500
C4—C5	1.378 (4)	C19—C20	1.365 (5)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.400 (4)	C20—C21	1.378 (5)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.376 (5)	C21—C22	1.376 (5)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.390 (4)	C22—H22	0.9500
C7—H7	0.9500

N2ⁱ—Pd1—N2	180.0	N3—C10—S2	120.5 (2)
N2ⁱ—Pd1—S1ⁱ	83.22 (7)	S1—C10—S2	112.65 (16)
N2—Pd1—S1ⁱ	96.78 (7)	C12—C11—S2	116.6 (2)
N2ⁱ—Pd1—S1	96.78 (7)	C12—C11—H11A	108.1
N2—Pd1—S1	83.22 (7)	S2—C11—H11A	108.1
S1ⁱ—Pd1—S1	180.0	C12—C11—H11B	108.1
C10—S1—Pd1	95.95 (11)	S2—C11—H11B	108.1
C10—S2—C11	104.39 (14)	H11A—C11—H11B	107.3
C1—N1—C8	109.9 (3)	C13—C12—C17	118.5 (3)
C1—N1—H1N	124 (2)	C13—C12—C11	121.7 (3)
C8—N1—H1N	126 (2)	C17—C12—C11	119.8 (3)
C9—N2—N3	114.6 (2)	C14—C13—C12	120.4 (3)
C9—N2—Pd1	124.4 (2)	C14—C13—H13	119.8
N3—N2—Pd1	121.06 (17)	C12—C13—H13	119.8
C10—N3—N2	112.8 (2)	C13—C14—C15	120.5 (3)
N1—C1—C2	110.1 (3)	C13—C14—H14	119.8
N1—C1—H1	125.0	C15—C14—H14	119.8
C2—C1—H1	125.0	C16—C15—C14	119.2 (3)
C1—C2—C9	131.8 (3)	C16—C15—H15	120.4
C1—C2—C3	105.7 (3)	C14—C15—H15	120.4
C9—C2—C3	122.4 (3)	C15—C16—C17	120.9 (3)
C8—C3—C4	118.9 (3)	C15—C16—H16	119.5
C8—C3—C2	106.7 (3)	C17—C16—H16	119.5
C4—C3—C2	134.3 (3)	C16—C17—C12	120.5 (3)
C5—C4—C3	118.1 (3)	C16—C17—H17	119.7
C5—C4—H4	121.0	C12—C17—H17	119.7
C3—C4—H4	121.0	C22—N4—C18	116.7 (3)
C4—C5—C6	121.9 (3)	N4—C18—C19	123.6 (3)
C4—C5—H5	119.1	N4—C18—H18	118.2
C6—C5—H5	119.1	C19—C18—H18	118.2
C7—C6—C5	121.1 (3)	C18—C19—C20	119.3 (3)
C7—C6—H6	119.4	C18—C19—H19	120.4
C5—C6—H6	119.4	C20—C19—H19	120.4
C6—C7—C8	117.3 (3)	C19—C20—C21	118.1 (4)
C6—C7—H7	121.4	C19—C20—H20	120.9
C8—C7—H7	121.4	C21—C20—H20	120.9
N1—C8—C7	129.7 (3)	C22—C21—C20	119.1 (4)
N1—C8—C3	107.6 (2)	C22—C21—H21	120.5
C7—C8—C3	122.7 (3)	C20—C21—H21	120.5
N2—C9—C2	130.7 (3)	N4—C22—C21	123.2 (3)
N2—C9—H9	114.7	N4—C22—H22	118.4
C2—C9—H9	114.7	C21—C22—H22	118.4
N3—C10—S1	126.8 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4	0.86 (2)	1.96 (2)	2.808 (4)	171 (3)
C9—H9···S1ⁱ	0.95	2.58	3.267 (3)	130
C1—H1···N3	0.95	2.42	2.889 (4)	110
C11—H11B···N3	0.99	2.50	2.937 (4)	106

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Pd(C₁₇H₁₄N₃S₂)₂]·2C₅H₅N
M_r	913.46
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.9688 (2), 10.5041 (2), 10.9491 (2)
α, β, γ (°)	62.534 (2), 78.494 (2), 78.985 (2)
V (Å³)	990.35 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.10 × 0.07 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8128, 3879, 3045
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.070, 0.99
No. of reflections	3879
No. of parameters	262
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −1.03

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
N1—H1N···N4	0.86 (2)	1.96 (2)	2.808 (4)	171 (3)
C9—H9···S1ⁱ	0.95	2.58	3.267 (3)	130

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors thank 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
Khaledi, H. & Mohd Ali, H. (2011). Acta Cryst. E67, m84. Web of Science CrossRef IUCr Journals Google Scholar
Khaledi, H., Mohd Ali, H. & Olmstead, M. M. (2011). Inorg. Chim. Acta, 366, 233–240. Web of Science CSD 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, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page m230

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