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

Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810051780

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m84

https://doi.org/10.1107/S1600536810051780

Open

access

Bis{benzyl 3-[(1H-indol-3-yl)methylidene]dithiocarbazato-κ²N³,S}palladium(II) N,N-dimethylformamide 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 8 December 2010; accepted 10 December 2010; online 15 December 2010)

In the title compound, [Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO, the deprotonated Schiff base ligand acts as an N,S-bidentate chelate, forming a five-membered ring with the metal atom. The Pd^II ion, located on an inversion center, is four-coordinated by two of the Schiff base ligands in a square-planar geometry. In the crystal, the indolic NH groups are bonded to the dimethylformamide (DMF) solvent molecules via an N—H⋯O interaction. In addition, C—H⋯S interactions are observed.

Related literature

For the crystal structure of the ligand, see: Khaledi et al. (2008 ). For the isotypic Cu(II) analog, see: Khaledi et al. (2009 ). For the Pd^II complex of the acetone Schiff base of S-methyldithiocarbazate, see: Ali et al. (2002 ).

Experimental

Crystal data

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO
M_r = 901.46
Monoclinic, P 2₁ /c
a = 10.509 (4) Å
b = 20.320 (7) Å
c = 10.925 (4) Å
β = 117.577 (5)°
V = 2067.8 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 296 K
0.30 × 0.15 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.818, T_max = 0.979
11353 measured reflections
4486 independent reflections
3411 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.074
S = 1.02
4486 reflections
255 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.84 (2)	1.91 (2)	2.749 (3)	174 (3)
C9—H9⋯S1ⁱ	0.93	2.60	3.279 (2)	130
Symmetry code: (i) -x+1, -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: https://doi.org/10.1107/S1600536810051780/pv2368sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051780/pv2368Isup2.hkl

checkCIF report

Comment top

The title compound is isostructural with the Cu^II complex of the Schiff base ligand (Khaledi et al., 2009). The palladium(II) ion is four-coordinated by two azomethine nitrogen and two thioamide sulfur atoms in a trans-square planar geometry. It has been suggested that the square planar geometry of the Schiff bases of S-alkyldithiocarbazate is trans when they are derived from aldehydes, whereas the ketone derivatives show cis geometry (Ali et al., 2002). Similar to the analogous Cu^II complex, the indole amino groups in the present structure are hydrogen bonded to the co-crystallized DMF molecules. Moreover, non-classical hydrogen bonds, C—H···N, C—H···O and C—H···S, are observed in the structure.

Related literature top

For the crystal structure of the ligand, see: Khaledi et al. (2008). For the isostructural copper analog, see: Khaledi et al. (2009). For the Pd^II complex of the acetone Shiff base of S-methyldithiocarbazate, see: Ali et al. (2002).

Experimental top

The Schiff base ligand was prepared as reported previously (Khaledi et al., 2008). 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 title crystals were obtained by slow evaporation of a solution of the solid in DMF.

Structure description top

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 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 radius.

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

Crystal data top

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO	F(000) = 928
M_r = 901.46	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3977 reflections
a = 10.509 (4) Å	θ = 2.3–29.4°
b = 20.320 (7) Å	µ = 0.70 mm⁻¹
c = 10.925 (4) Å	T = 296 K
β = 117.577 (5)°	Plate, red
V = 2067.8 (12) Å³	0.30 × 0.15 × 0.03 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.818, T_max = 0.979	k = −25→25
11353 measured reflections	l = −11→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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0332P)² + 0.5126P] where P = (F_o² + 2F_c²)/3
4486 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO	V = 2067.8 (12) Å³
M_r = 901.46	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.509 (4) Å	µ = 0.70 mm⁻¹
b = 20.320 (7) Å	T = 296 K
c = 10.925 (4) Å	0.30 × 0.15 × 0.03 mm
β = 117.577 (5)°

Data collection top

Bruker APEXII CCD diffractometer	4486 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3411 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.979	R_int = 0.024
11353 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.27 e Å⁻³
4486 reflections	Δρ_min = −0.31 e Å⁻³
255 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	0.5000	0.5000	1.0000	0.03881 (8)
S1	0.50770 (7)	0.38703 (3)	1.00654 (7)	0.05372 (16)
S2	0.60819 (8)	0.29517 (3)	0.86690 (7)	0.05937 (18)
N1	0.7185 (2)	0.50542 (10)	0.5369 (2)	0.0550 (5)
H1N	0.753 (3)	0.4818 (12)	0.496 (3)	0.066*
N2	0.56951 (19)	0.48716 (8)	0.85694 (19)	0.0422 (4)
N3	0.60342 (19)	0.42432 (8)	0.82622 (19)	0.0438 (4)
C1	0.6788 (3)	0.48235 (11)	0.6292 (3)	0.0517 (6)
H1	0.6771	0.4381	0.6505	0.062*
C2	0.6405 (2)	0.53413 (10)	0.6881 (2)	0.0438 (5)
C3	0.6598 (2)	0.59335 (10)	0.6243 (2)	0.0434 (5)
C4	0.6429 (3)	0.66054 (11)	0.6388 (3)	0.0547 (6)
H4	0.6111	0.6755	0.7005	0.066*
C5	0.6739 (3)	0.70436 (13)	0.5604 (3)	0.0667 (7)
H5	0.6642	0.7493	0.5703	0.080*
C6	0.7198 (3)	0.68253 (13)	0.4660 (3)	0.0692 (8)
H6	0.7388	0.7132	0.4134	0.083*
C7	0.7374 (3)	0.61730 (13)	0.4495 (3)	0.0595 (6)
H7	0.7678	0.6029	0.3865	0.071*
C8	0.7080 (2)	0.57292 (11)	0.5304 (2)	0.0479 (5)
C9	0.5902 (2)	0.53485 (11)	0.7881 (2)	0.0449 (5)
H9	0.5681	0.5765	0.8081	0.054*
C10	0.5759 (2)	0.37785 (10)	0.8902 (2)	0.0424 (5)
C11	0.6598 (3)	0.29661 (12)	0.7301 (3)	0.0587 (6)
H11A	0.6411	0.2533	0.6880	0.070*
H11B	0.5969	0.3273	0.6602	0.070*
C12	0.8120 (3)	0.31475 (10)	0.7668 (3)	0.0514 (6)
C13	0.8432 (3)	0.32943 (13)	0.6598 (3)	0.0641 (7)
H13	0.7699	0.3284	0.5694	0.077*
C14	0.9801 (3)	0.34555 (15)	0.6844 (4)	0.0792 (9)
H14	0.9987	0.3548	0.6108	0.095*
C15	1.0875 (3)	0.34793 (16)	0.8149 (4)	0.0858 (10)
H15	1.1798	0.3595	0.8316	0.103*
C16	1.0600 (3)	0.33329 (16)	0.9226 (4)	0.0884 (10)
H16	1.1340	0.3348	1.0126	0.106*
C17	0.9222 (3)	0.31618 (14)	0.8987 (3)	0.0706 (7)
H17	0.9050	0.3057	0.9726	0.085*
O1	0.8241 (4)	0.43495 (13)	0.3888 (3)	0.1248 (10)
N4	0.9096 (2)	0.42640 (11)	0.2347 (2)	0.0634 (6)
C18	0.8601 (4)	0.45922 (17)	0.3077 (4)	0.0946 (11)
H18	0.8520	0.5046	0.2964	0.113*
C19	0.9457 (3)	0.45852 (16)	0.1364 (3)	0.0827 (9)
H19A	0.9369	0.5053	0.1420	0.124*
H19B	0.8815	0.4438	0.0448	0.124*
H19C	1.0426	0.4477	0.1574	0.124*
C20	0.9206 (3)	0.35570 (14)	0.2455 (3)	0.0785 (8)
H20A	0.9153	0.3418	0.3269	0.118*
H20B	1.0106	0.3420	0.2511	0.118*
H20C	0.8432	0.3363	0.1656	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.04047 (13)	0.04106 (13)	0.04411 (14)	0.00056 (10)	0.02740 (11)	0.00044 (11)
S1	0.0737 (4)	0.0436 (3)	0.0685 (4)	−0.0004 (3)	0.0537 (4)	0.0015 (3)
S2	0.0807 (4)	0.0410 (3)	0.0797 (5)	−0.0021 (3)	0.0569 (4)	−0.0023 (3)
N1	0.0705 (13)	0.0540 (12)	0.0608 (13)	−0.0030 (10)	0.0477 (11)	−0.0044 (10)
N2	0.0469 (10)	0.0428 (10)	0.0467 (10)	0.0017 (7)	0.0301 (9)	−0.0002 (8)
N3	0.0503 (10)	0.0407 (9)	0.0511 (11)	0.0002 (8)	0.0325 (9)	−0.0031 (8)
C1	0.0656 (15)	0.0462 (12)	0.0603 (15)	−0.0024 (11)	0.0434 (13)	0.0003 (11)
C2	0.0495 (12)	0.0444 (12)	0.0480 (13)	0.0014 (10)	0.0314 (11)	0.0026 (10)
C3	0.0426 (11)	0.0470 (12)	0.0466 (12)	0.0015 (10)	0.0257 (10)	0.0046 (10)
C4	0.0573 (14)	0.0507 (13)	0.0664 (16)	0.0053 (11)	0.0374 (13)	0.0056 (12)
C5	0.0681 (17)	0.0505 (14)	0.089 (2)	0.0026 (12)	0.0431 (16)	0.0135 (14)
C6	0.0660 (17)	0.0691 (17)	0.082 (2)	−0.0025 (13)	0.0426 (16)	0.0267 (15)
C7	0.0599 (15)	0.0741 (17)	0.0586 (16)	−0.0024 (13)	0.0394 (13)	0.0115 (13)
C8	0.0475 (12)	0.0546 (13)	0.0490 (13)	−0.0030 (10)	0.0287 (11)	0.0032 (11)
C9	0.0513 (13)	0.0404 (11)	0.0528 (14)	0.0030 (10)	0.0323 (12)	0.0018 (10)
C10	0.0432 (11)	0.0430 (11)	0.0487 (13)	−0.0026 (9)	0.0278 (11)	−0.0040 (10)
C11	0.0702 (16)	0.0537 (14)	0.0667 (16)	−0.0089 (12)	0.0440 (14)	−0.0186 (12)
C12	0.0610 (15)	0.0404 (11)	0.0645 (16)	0.0026 (10)	0.0389 (14)	−0.0099 (11)
C13	0.0680 (17)	0.0654 (16)	0.0694 (17)	0.0005 (13)	0.0409 (15)	−0.0041 (14)
C14	0.076 (2)	0.082 (2)	0.101 (3)	0.0005 (17)	0.059 (2)	0.0081 (19)
C15	0.0625 (19)	0.082 (2)	0.122 (3)	0.0053 (16)	0.050 (2)	0.009 (2)
C16	0.0637 (19)	0.095 (2)	0.089 (2)	0.0093 (17)	0.0210 (18)	−0.0057 (19)
C17	0.0734 (19)	0.0774 (18)	0.0687 (19)	0.0053 (15)	0.0393 (17)	−0.0040 (15)
O1	0.202 (3)	0.120 (2)	0.1058 (19)	0.0498 (19)	0.116 (2)	0.0098 (16)
N4	0.0643 (13)	0.0729 (14)	0.0570 (13)	0.0028 (11)	0.0315 (12)	−0.0111 (11)
C18	0.136 (3)	0.080 (2)	0.086 (2)	0.026 (2)	0.067 (2)	−0.0029 (19)
C19	0.079 (2)	0.095 (2)	0.083 (2)	−0.0068 (17)	0.0451 (19)	−0.0070 (18)
C20	0.090 (2)	0.0727 (19)	0.073 (2)	0.0108 (16)	0.0386 (18)	−0.0092 (16)

Geometric parameters (Å, º) top

Pd1—N2ⁱ	2.0252 (18)	C9—H9	0.9300
Pd1—N2	2.0252 (18)	C11—C12	1.505 (3)
Pd1—S1	2.2969 (10)	C11—H11A	0.9700
Pd1—S1ⁱ	2.2969 (10)	C11—H11B	0.9700
S1—C10	1.735 (2)	C12—C17	1.369 (4)
S2—C10	1.755 (2)	C12—C13	1.384 (3)
S2—C11	1.810 (2)	C13—C14	1.376 (4)
N1—C1	1.342 (3)	C13—H13	0.9300
N1—C8	1.375 (3)	C14—C15	1.349 (4)
N1—H1N	0.840 (16)	C14—H14	0.9300
N2—C9	1.305 (3)	C15—C16	1.368 (4)
N2—N3	1.407 (2)	C15—H15	0.9300
N3—C10	1.285 (3)	C16—C17	1.391 (4)
C1—C2	1.387 (3)	C16—H16	0.9300
C1—H1	0.9300	C17—H17	0.9300
C2—C9	1.417 (3)	O1—C18	1.218 (4)
C2—C3	1.451 (3)	N4—C18	1.317 (4)
C3—C4	1.395 (3)	N4—C20	1.442 (3)
C3—C8	1.401 (3)	N4—C19	1.449 (4)
C4—C5	1.375 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.398 (4)	C19—H19B	0.9600
C5—H5	0.9300	C19—H19C	0.9600
C6—C7	1.362 (4)	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—C8	1.394 (3)	C20—H20C	0.9600
C7—H7	0.9300

N2ⁱ—Pd1—N2	179.999 (1)	S1—C10—S2	112.47 (12)
N2ⁱ—Pd1—S1	97.17 (5)	C12—C11—S2	118.18 (19)
N2—Pd1—S1	82.83 (5)	C12—C11—H11A	107.8
N2ⁱ—Pd1—S1ⁱ	82.83 (5)	S2—C11—H11A	107.8
N2—Pd1—S1ⁱ	97.17 (5)	C12—C11—H11B	107.8
S1—Pd1—S1ⁱ	180.0	S2—C11—H11B	107.8
C10—S1—Pd1	96.04 (7)	H11A—C11—H11B	107.1
C10—S2—C11	104.82 (11)	C17—C12—C13	118.0 (2)
C1—N1—C8	109.95 (19)	C17—C12—C11	124.2 (2)
C1—N1—H1N	123.9 (19)	C13—C12—C11	117.8 (2)
C8—N1—H1N	125.9 (19)	C14—C13—C12	121.4 (3)
C9—N2—N3	114.08 (17)	C14—C13—H13	119.3
C9—N2—Pd1	124.40 (15)	C12—C13—H13	119.3
N3—N2—Pd1	121.50 (12)	C15—C14—C13	120.2 (3)
C10—N3—N2	113.06 (17)	C15—C14—H14	119.9
N1—C1—C2	110.0 (2)	C13—C14—H14	119.9
N1—C1—H1	125.0	C14—C15—C16	119.6 (3)
C2—C1—H1	125.0	C14—C15—H15	120.2
C1—C2—C9	131.1 (2)	C16—C15—H15	120.2
C1—C2—C3	105.77 (19)	C15—C16—C17	120.6 (3)
C9—C2—C3	123.12 (19)	C15—C16—H16	119.7
C4—C3—C8	118.8 (2)	C17—C16—H16	119.7
C4—C3—C2	134.7 (2)	C12—C17—C16	120.2 (3)
C8—C3—C2	106.49 (18)	C12—C17—H17	119.9
C5—C4—C3	118.9 (2)	C16—C17—H17	119.9
C5—C4—H4	120.5	C18—N4—C20	119.6 (3)
C3—C4—H4	120.5	C18—N4—C19	122.2 (3)
C4—C5—C6	121.1 (2)	C20—N4—C19	118.1 (2)
C4—C5—H5	119.5	O1—C18—N4	125.4 (3)
C6—C5—H5	119.5	O1—C18—H18	117.3
C7—C6—C5	121.4 (2)	N4—C18—H18	117.3
C7—C6—H6	119.3	N4—C19—H19A	109.5
C5—C6—H6	119.3	N4—C19—H19B	109.5
C6—C7—C8	117.5 (2)	H19A—C19—H19B	109.5
C6—C7—H7	121.2	N4—C19—H19C	109.5
C8—C7—H7	121.2	H19A—C19—H19C	109.5
N1—C8—C7	129.9 (2)	H19B—C19—H19C	109.5
N1—C8—C3	107.81 (18)	N4—C20—H20A	109.5
C7—C8—C3	122.3 (2)	N4—C20—H20B	109.5
N2—C9—C2	131.1 (2)	H20A—C20—H20B	109.5
N2—C9—H9	114.4	N4—C20—H20C	109.5
C2—C9—H9	114.4	H20A—C20—H20C	109.5
N3—C10—S1	126.36 (16)	H20B—C20—H20C	109.5
N3—C10—S2	121.17 (16)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (2)	1.91 (2)	2.749 (3)	174 (3)
C1—H1···N3	0.93	2.40	2.869 (3)	111
C17—H17···S2	0.93	2.79	3.183 (3)	107
C20—H20A···O1	0.96	2.36	2.747 (3)	104
C9—H9···S1ⁱ	0.93	2.60	3.279 (2)	130

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO
M_r	901.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.509 (4), 20.320 (7), 10.925 (4)
β (°)	117.577 (5)
V (Å³)	2067.8 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.30 × 0.15 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.818, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	11353, 4486, 3411
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 1.02
No. of reflections	4486
No. of parameters	255
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)	0.27, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.840 (16)	1.912 (17)	2.749 (3)	174 (3)
C1—H1···N3	0.93	2.40	2.869 (3)	111.4
C17—H17···S2	0.93	2.79	3.183 (3)	106.8
C20—H20A···O1	0.96	2.36	2.747 (3)	103.6
C9—H9···S1ⁱ	0.93	2.60	3.279 (2)	129.9

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The authors thank University of Malaya for funding this study (UMRG grant RG024/09BIO).

References

Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali, A. M. (2002). J. Inorg. Biochem. 92, 141–148. CSD CrossRef PubMed Google Scholar
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. & Ng, S. W. (2008). Acta Cryst. E64, o2107. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m139. Web of Science CSD CrossRef IUCr Journals 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

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m84

https://doi.org/10.1107/S1600536810051780

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)