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Acta Cryst. (2009). E65, m1059    [ doi:10.1107/S1600536809029262 ]

cis-Bis[1-allyl-3-(2-pyridyl-[kappa]N)thioureato-[kappa]S]palladium(II)

S. Orysyk, V. Bon and V. Pekhnyo

Abstract top

Yellow plate-like shaped crystals of the title compound, [Pd(C9H10N3S)2], were obtained by ligand-exchange reaction between palladium(II) acetylacetonate and the corresponding organic reagent at room temperature. The PdII atom shows a slightly distorted square-planar coordination geometry consisting of two ligand molecules in a cis conformation that bind in their thiolic tautomeric form. Weak intermolecular Pd...H interactions with Pd-H distances of 3.328 (2) Å were observed in the crystal structure. The three-dimensional network of the crystal structure is realized by weak intermolecular C-H...N, N-H...N and C-H...S hydrogen bonds.

Comment top

Palladium complexes with carbothioamide derivatives as organic ligands attract ongoing scientific interest due to their cytotoxic, antitumoral, antifungal and antimicrobial activities (Upadhayaya et al. 2009; Hernández et al. 2008)

The asymmetric unit of the title compound contains one molecule of the complex (Fig. 1). Palladium shows a slightly distorted square-planar coordination geometry with a mean deviation from the plane of 0.0679 (2) Å. Two molecules of the organic ligand chelate the palladium in cis-conformation via carbothioamide sulfur and pyridine nitrogen atoms. The observed bond lengths of the carbothioamide fragment [C(6)—S(1) 1.752 (2), C(15)—S(2) 1.753 (2), C(6)—N(2) 1.301 (3) and C(15)—N(5) 1.302 (3) Å] indicate the thiolic tautomeric form of the thiourea derivative. The six-membered metallacycle exhibits a non-planar geometry with torsion angles Pd(1)—S(1)—C(6)—N(2) 142.8 (2) and Pd(1)—S(2)—C(15)—N(5) 134.1 (2)°. The allyl substituents of both coordinated ligand molecules are disordered over two positions with occupancies of 0.7 and 0.3, respectively. The crystal structure of the title compound shows weak intermolecular Pd···H interactions with d(Pd—H) = 3.328 Å. The 3-D network is realized by weak C—H···N, N—H···N and C—H···S intermolecular hydrogen bonds (Fig.2, Table 1).

Related literature top

For a related structure, see: Bon et al. (2007). For the antitumoral properties of Pd compounds, see: Upadhayaya et al. (2009), Hernández et al. (2008).

Experimental top

Single crystals of title compound were synthesized by a ligand exchange reaction between 5 ml (5x10-3 M) of a solution of palladium(II) acetylacetonate in chloroform and 5 ml (10-2 M) of an ethanolic solution of the organic ligand. After staying one month in a dark place the layered mixture becomes homogeneous and yellow plate-like shaped crystals were grown.

Refinement top

Disorder of both allyl fragments has been observed in the molecular structure of the title compound. Disordered allyl substituents C8, C9 and C17, C18 were treated with occupancies 0.71/0.29 and 0.70/0.30, respectively, and refined with equal ADP for both parts. H atoms bonded to N were located in a difference map and refined freely. Other H atoms were positioned geometrically and refined using a riding model with C—H = 0.99 Å for CH2 [Uiso(H) = 1.2Ueq(C)] and C—H = 0.95 Å for CH [Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. The title compound showing 50% probability displacement ellipsoids for the non-hydrogen atoms. Only one position is shown for disordered allyl fragments
[Figure 2] Fig. 2. Crystal packing of title compound, projection down the a axis. Dashed lines indicate hydrogen bonds.
cis-Bis[1-allyl-3-(2-pyridyl-κN)thioureato- κS]palladium(II) top
Crystal data top
[Pd(C9H10N3S)2]F(000) = 992
Mr = 490.96Dx = 1.670 Mg m−3
Monoclinic, P21/cMelting point: 343 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.8976 (6) ÅCell parameters from 8451 reflections
b = 8.9730 (5) Åθ = 3.0–26.4°
c = 21.798 (1) ŵ = 1.18 mm−1
β = 113.624 (2)°T = 173 K
V = 1952.9 (2) Å3Plate, yellow
Z = 40.51 × 0.21 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer		4010 independent reflections
Radiation source: fine-focus sealed tube3522 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 8.26 pixels mm-1θmax = 26.4°, θmin = 2.0°
φ and ω scansh = −13→13
Absorption correction: numerical
(SADABS; Bruker, 2005)		k = −11→11
Tmin = 0.583, Tmax = 0.941l = −26→27
17417 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.02P)2 + 1.8761P]
where P = (Fo2 + 2Fc2)/3
4010 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.58 e Å−3
3 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Pd(C9H10N3S)2]V = 1952.9 (2) Å3
Mr = 490.96Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.8976 (6) ŵ = 1.18 mm−1
b = 8.9730 (5) ÅT = 173 K
c = 21.798 (1) Å0.51 × 0.21 × 0.05 mm
β = 113.624 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		4010 independent reflections
Absorption correction: numerical
(SADABS; Bruker, 2005)		3522 reflections with I > 2σ(I)
Tmin = 0.583, Tmax = 0.941Rint = 0.026
17417 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055Δρmax = 0.58 e Å−3
S = 1.03Δρmin = −0.37 e Å−3
4010 reflectionsAbsolute structure: ?
272 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Pd10.504182 (15)0.273165 (18)0.331038 (7)0.02144 (6)
S10.48920 (6)0.26120 (8)0.43136 (3)0.03554 (15)
S20.72854 (5)0.24180 (7)0.38621 (3)0.02877 (13)
N10.30161 (17)0.3217 (2)0.28592 (8)0.0226 (4)
N20.22927 (17)0.1688 (2)0.35666 (9)0.0246 (4)
N30.3409 (2)0.0682 (3)0.45961 (10)0.0356 (5)
N40.52967 (17)0.26693 (19)0.24180 (8)0.0216 (4)
N50.73705 (17)0.4037 (2)0.27993 (8)0.0238 (4)
N60.88430 (19)0.4612 (2)0.38499 (10)0.0330 (5)
C10.2066 (2)0.2704 (2)0.30613 (10)0.0231 (4)
C20.0738 (2)0.3203 (3)0.27361 (11)0.0282 (5)
H2A0.00670.28030.28620.034*
C30.0396 (2)0.4252 (3)0.22420 (11)0.0303 (5)
H3A−0.05000.46000.20330.036*
C40.1382 (2)0.4802 (3)0.20512 (11)0.0299 (5)
H4A0.11770.55360.17100.036*
C50.2656 (2)0.4259 (2)0.23664 (11)0.0268 (5)
H5A0.33270.46330.22330.032*
C60.3393 (2)0.1622 (3)0.41056 (10)0.0262 (5)
C70.2192 (3)0.0080 (3)0.46317 (13)0.0396 (6)
H7A0.2445−0.06450.50050.048*
H7B0.1673−0.04610.42110.048*
C8A0.1310 (4)0.1276 (5)0.4737 (2)0.0501 (10)0.711 (5)
H8AA0.08850.19630.43830.060*0.711 (5)
C9A0.1099 (12)0.1423 (10)0.5274 (5)0.0819 (19)0.711 (5)
H9AA0.15070.07550.56380.098*0.711 (5)
H9AB0.05340.21980.53070.098*0.711 (5)
C8B0.1993 (11)0.0863 (13)0.5186 (6)0.0501 (10)0.289 (5)
H8BA0.26300.06960.56300.060*0.289 (5)
C9B0.103 (3)0.173 (3)0.5105 (16)0.0819 (19)0.289 (5)
H9BA0.03770.19240.46680.098*0.289 (5)
H9BB0.09620.21990.54810.098*0.289 (5)
C100.6369 (2)0.3219 (2)0.23255 (10)0.0230 (4)
C110.6465 (2)0.3015 (3)0.17078 (11)0.0332 (5)
H11A0.71890.34520.16350.040*
C120.5531 (3)0.2197 (3)0.12094 (12)0.0377 (6)
H12A0.56130.20410.07970.045*
C130.4457 (2)0.1597 (3)0.13180 (11)0.0350 (5)
H13A0.37980.10130.09840.042*
C140.4373 (2)0.1868 (3)0.19154 (11)0.0289 (5)
H14A0.36280.14760.19840.035*
C150.7807 (2)0.3775 (2)0.34392 (10)0.0240 (4)
C160.9495 (2)0.5766 (3)0.36190 (13)0.0380 (6)
H16A0.90160.67150.35980.046*
H16B0.93750.55150.31560.046*
C17A1.0931 (6)0.6027 (8)0.4014 (4)0.0486 (15)0.700 (9)
H17A1.12960.69140.39180.058*0.700 (9)
C18A1.1731 (5)0.5195 (7)0.4466 (3)0.0540 (13)0.700 (9)
H18A1.14190.42940.45810.065*0.700 (9)
H18B1.26450.54730.46910.065*0.700 (9)
C17B1.0811 (14)0.6032 (17)0.4263 (6)0.037 (3)0.300 (9)
H17B1.07450.64690.46450.044*0.300 (9)
C18B1.2000 (13)0.5671 (16)0.4290 (7)0.0540 (13)0.300 (9)
H18C1.20850.52330.39120.065*0.300 (9)
H18D1.27750.58470.46870.065*0.300 (9)
H6N0.904 (2)0.452 (3)0.4237 (13)0.027 (7)*
H3N0.404 (3)0.072 (3)0.4936 (13)0.038 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01747 (9)0.02785 (10)0.01790 (9)−0.00036 (7)0.00594 (6)0.00161 (6)
S10.0235 (3)0.0626 (4)0.0191 (3)−0.0085 (3)0.0070 (2)−0.0001 (3)
S20.0197 (3)0.0401 (3)0.0239 (3)0.0029 (2)0.0061 (2)0.0081 (2)
N10.0208 (9)0.0246 (9)0.0209 (9)0.0000 (7)0.0067 (7)0.0016 (7)
N20.0226 (9)0.0260 (9)0.0244 (9)−0.0010 (8)0.0086 (7)0.0030 (7)
N30.0307 (11)0.0493 (13)0.0246 (10)0.0025 (10)0.0089 (9)0.0118 (9)
N40.0207 (9)0.0228 (9)0.0203 (9)−0.0008 (7)0.0071 (7)0.0007 (7)
N50.0204 (9)0.0259 (10)0.0247 (9)−0.0012 (7)0.0084 (7)0.0003 (7)
N60.0257 (11)0.0419 (12)0.0250 (11)−0.0068 (9)0.0035 (9)−0.0041 (9)
C10.0230 (11)0.0212 (10)0.0240 (10)−0.0029 (9)0.0082 (9)−0.0029 (8)
C20.0198 (11)0.0314 (12)0.0317 (12)−0.0025 (9)0.0086 (9)0.0007 (9)
C30.0205 (11)0.0319 (13)0.0320 (12)0.0035 (9)0.0038 (9)0.0020 (10)
C40.0302 (12)0.0273 (12)0.0272 (11)0.0008 (10)0.0064 (9)0.0053 (9)
C50.0253 (11)0.0292 (12)0.0253 (11)−0.0022 (9)0.0093 (9)0.0022 (9)
C60.0241 (11)0.0323 (12)0.0244 (11)0.0032 (9)0.0120 (9)0.0011 (9)
C70.0474 (16)0.0395 (14)0.0343 (13)−0.0108 (12)0.0188 (12)0.0048 (11)
C8A0.042 (2)0.068 (3)0.049 (2)0.0008 (19)0.0275 (18)0.005 (2)
C9A0.133 (4)0.060 (5)0.081 (7)0.006 (4)0.072 (5)0.018 (3)
C8B0.042 (2)0.068 (3)0.049 (2)0.0008 (19)0.0275 (18)0.005 (2)
C9B0.133 (4)0.060 (5)0.081 (7)0.006 (4)0.072 (5)0.018 (3)
C100.0230 (11)0.0209 (10)0.0247 (10)0.0013 (8)0.0091 (9)0.0024 (8)
C110.0315 (13)0.0446 (15)0.0269 (12)−0.0040 (11)0.0153 (10)0.0024 (10)
C120.0433 (15)0.0479 (15)0.0233 (12)−0.0028 (12)0.0148 (11)−0.0041 (10)
C130.0388 (14)0.0365 (14)0.0238 (11)−0.0081 (11)0.0064 (10)−0.0074 (10)
C140.0263 (12)0.0299 (12)0.0275 (11)−0.0055 (10)0.0077 (9)−0.0019 (9)
C150.0191 (10)0.0245 (11)0.0281 (11)0.0034 (9)0.0094 (9)−0.0023 (9)
C160.0321 (13)0.0382 (14)0.0427 (14)−0.0109 (11)0.0139 (11)−0.0101 (11)
C17A0.033 (3)0.045 (3)0.063 (4)−0.013 (2)0.014 (3)−0.002 (3)
C18A0.038 (3)0.059 (4)0.054 (3)−0.009 (2)0.0074 (19)0.005 (2)
C17B0.039 (6)0.035 (5)0.045 (7)−0.015 (4)0.026 (6)−0.011 (5)
C18B0.038 (3)0.059 (4)0.054 (3)−0.009 (2)0.0074 (19)0.005 (2)
Geometric parameters (Å, °) top
Pd1—N12.0713 (17)C7—H7A0.9900
Pd1—N42.0730 (17)C7—H7B0.9900
Pd1—S12.2598 (6)C8A—C9A1.288 (7)
Pd1—S22.2686 (6)C8A—H8AA0.9500
S1—C61.752 (2)C9A—H9AA0.9500
S2—C151.753 (2)C9A—H9AB0.9500
N1—C11.358 (3)C8B—C9B1.261 (17)
N1—C51.358 (3)C8B—H8BA0.9500
N2—C61.301 (3)C9B—H9BA0.9500
N2—C11.374 (3)C9B—H9BB0.9500
N3—C61.357 (3)C10—C111.404 (3)
N3—C71.463 (3)C11—C121.367 (3)
N3—H3N0.78 (3)C11—H11A0.9500
N4—C101.355 (3)C12—C131.392 (4)
N4—C141.359 (3)C12—H12A0.9500
N5—C151.302 (3)C13—C141.363 (3)
N5—C101.376 (3)C13—H13A0.9500
N6—C151.353 (3)C14—H14A0.9500
N6—C161.455 (3)C16—C17A1.471 (7)
N6—H6N0.79 (2)C16—C17B1.572 (13)
C1—C21.405 (3)C16—H16A0.9900
C2—C31.365 (3)C16—H16B0.9900
C2—H2A0.9500C17A—C18A1.265 (9)
C3—C41.389 (3)C17A—H17A0.9500
C3—H3A0.9500C18A—H18A0.9500
C4—C51.368 (3)C18A—H18B0.9500
C4—H4A0.9500C17B—C18B1.31 (2)
C5—H5A0.9500C17B—H17B0.9500
C7—C8B1.487 (11)C18B—H18C0.9500
C7—C8A1.519 (5)C18B—H18D0.9500
N1—Pd1—N494.48 (7)C9A—C8A—H8AA117.8
N1—Pd1—S189.59 (5)C7—C8A—H8AA117.8
N4—Pd1—S1174.63 (5)C8A—C9A—H9AA120.0
N1—Pd1—S2174.24 (5)C8A—C9A—H9AB120.0
N4—Pd1—S288.44 (5)H9AA—C9A—H9AB120.0
S1—Pd1—S287.80 (2)C9B—C8B—C7124.2 (18)
C6—S1—Pd1101.25 (7)C9B—C8B—H8BA117.9
C15—S2—Pd198.20 (7)C7—C8B—H8BA117.9
C1—N1—C5118.27 (18)C8B—C9B—H9BA120.0
C1—N1—Pd1125.52 (14)C8B—C9B—H9BB120.0
C5—N1—Pd1115.82 (14)H9BA—C9B—H9BB120.0
C6—N2—C1123.98 (19)N4—C10—N5123.65 (18)
C6—N3—C7123.1 (2)N4—C10—C11119.71 (19)
C6—N3—H3N116 (2)N5—C10—C11116.58 (19)
C7—N3—H3N116 (2)C12—C11—C10120.9 (2)
C10—N4—C14118.47 (18)C12—C11—H11A119.5
C10—N4—Pd1125.27 (14)C10—C11—H11A119.5
C14—N4—Pd1115.87 (14)C11—C12—C13118.8 (2)
C15—N5—C10123.16 (18)C11—C12—H12A120.6
C15—N6—C16124.1 (2)C13—C12—H12A120.6
C15—N6—H6N116.6 (18)C14—C13—C12118.5 (2)
C16—N6—H6N118.9 (18)C14—C13—H13A120.8
N1—C1—N2124.70 (19)C12—C13—H13A120.8
N1—C1—C2119.55 (19)N4—C14—C13123.6 (2)
N2—C1—C2115.73 (19)N4—C14—H14A118.2
C3—C2—C1121.2 (2)C13—C14—H14A118.2
C3—C2—H2A119.4N5—C15—N6117.3 (2)
C1—C2—H2A119.4N5—C15—S2129.22 (17)
C2—C3—C4118.8 (2)N6—C15—S2113.46 (16)
C2—C3—H3A120.6N6—C16—C17A117.6 (3)
C4—C3—H3A120.6N6—C16—C17B101.3 (5)
C5—C4—C3118.3 (2)N6—C16—H16A107.9
C5—C4—H4A120.8C17A—C16—H16A107.9
C3—C4—H4A120.8C17B—C16—H16A100.7
N1—C5—C4123.8 (2)N6—C16—H16B107.9
N1—C5—H5A118.1C17A—C16—H16B107.9
C4—C5—H5A118.1C17B—C16—H16B130.2
N2—C6—N3117.1 (2)H16A—C16—H16B107.2
N2—C6—S1129.58 (17)C18A—C17A—C16127.0 (6)
N3—C6—S1113.29 (17)C18A—C17A—H17A116.5
N3—C7—C8B107.4 (4)C16—C17A—H17A116.5
N3—C7—C8A112.9 (2)C17A—C18A—H18A120.0
N3—C7—H7A109.0C17A—C18A—H18B120.0
C8B—C7—H7A74.1H18A—C18A—H18B120.0
C8A—C7—H7A109.0C18B—C17B—C16122.2 (12)
N3—C7—H7B109.0C18B—C17B—H17B118.9
C8B—C7—H7B140.3C16—C17B—H17B118.9
C8A—C7—H7B109.0C17B—C18B—H18C120.0
H7A—C7—H7B107.8C17B—C18B—H18D120.0
C9A—C8A—C7124.3 (5)H18C—C18B—H18D120.0
N1—Pd1—S1—C642.71 (9)C6—N3—C7—C8B−106.2 (5)
S2—Pd1—S1—C6−142.43 (8)C6—N3—C7—C8A−63.7 (3)
N4—Pd1—S2—C1547.84 (9)N3—C7—C8A—C9A−112.2 (8)
S1—Pd1—S2—C15−136.00 (7)C8B—C7—C8A—C9A−22.0 (10)
N4—Pd1—N1—C1143.98 (17)N3—C7—C8B—C9B113.5 (19)
S1—Pd1—N1—C1−32.53 (17)C8A—C7—C8B—C9B8.4 (18)
N4—Pd1—N1—C5−43.35 (16)C14—N4—C10—N5−179.6 (2)
S1—Pd1—N1—C5140.15 (15)Pd1—N4—C10—N5−7.2 (3)
N1—Pd1—N4—C10140.26 (17)C14—N4—C10—C113.2 (3)
S2—Pd1—N4—C10−34.78 (16)Pd1—N4—C10—C11175.61 (16)
N1—Pd1—N4—C14−47.14 (16)C15—N5—C10—N436.3 (3)
S2—Pd1—N4—C14137.82 (15)C15—N5—C10—C11−146.4 (2)
C5—N1—C1—N2−177.9 (2)N4—C10—C11—C12−3.8 (4)
Pd1—N1—C1—N2−5.4 (3)N5—C10—C11—C12178.9 (2)
C5—N1—C1—C23.2 (3)C10—C11—C12—C131.7 (4)
Pd1—N1—C1—C2175.69 (15)C11—C12—C13—C140.8 (4)
C6—N2—C1—N135.3 (3)C10—N4—C14—C13−0.7 (3)
C6—N2—C1—C2−145.8 (2)Pd1—N4—C14—C13−173.80 (19)
N1—C1—C2—C3−3.3 (3)C12—C13—C14—N4−1.4 (4)
N2—C1—C2—C3177.6 (2)C10—N5—C15—N6176.7 (2)
C1—C2—C3—C41.5 (3)C10—N5—C15—S2−0.6 (3)
C2—C3—C4—C50.3 (3)C16—N6—C15—N5−0.5 (3)
C1—N1—C5—C4−1.4 (3)C16—N6—C15—S2177.21 (18)
Pd1—N1—C5—C4−174.65 (18)Pd1—S2—C15—N5−45.9 (2)
C3—C4—C5—N1−0.4 (4)Pd1—S2—C15—N6136.77 (15)
C1—N2—C6—N3172.1 (2)C15—N6—C16—C17A−148.5 (4)
C1—N2—C6—S1−6.3 (3)C15—N6—C16—C17B−165.4 (6)
C7—N3—C6—N2−17.4 (3)N6—C16—C17A—C18A13.5 (10)
C7—N3—C6—S1161.29 (19)C17B—C16—C17A—C18A61.2 (18)
Pd1—S1—C6—N2−37.2 (2)N6—C16—C17B—C18B112.2 (14)
Pd1—S1—C6—N3144.37 (16)C17A—C16—C17B—C18B−25.9 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···N2i0.952.643.511 (3)152
C14—H14A···N5ii0.952.573.376 (3)143
N3—H3N···N3iii0.78 (3)2.84 (3)3.425 (4)133 (2)
C4—H4A···S2iv0.952.983.728 (2)136
C12—H12A···S1v0.953.023.910 (2)156
C18B—H18D···S1vi0.952.953.85 (1)160
C7—H7A···S2iii0.992.853.825 (3)167
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+2, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···N2i0.952.643.511 (3)152
C14—H14A···N5ii0.952.573.376 (3)143
N3—H3N···N3iii0.78 (3)2.84 (3)3.425 (4)133 (2)
C4—H4A···S2iv0.952.983.728 (2)136
C12—H12A···S1v0.953.023.910 (2)156
C18B—H18D···S1vi0.952.953.85 (1)160
C7—H7A···S2iii0.992.853.825 (3)167
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+2, −y+1, −z+1.
references
References top

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Hernández, W., Paz, J., Vaisberg, A., Spodine, E., Richter, R. & Beyer, L. (2008). Bioinorg. Chem. Appl. pp. 1–10

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Upadhayaya, R. S., Kulkarni, G. M., Vasireddy, N. R., Vandavasi, J. K., Dixit, S. S., Sharma, V. & Chattopadhyaya, J. (2009). Bioorg. Med. Chem. 17, 4681–4692.

Westrip, S. P. (2009). publCIF. In preparation.