Bis(1,3-dibutylthiourea)dicyanido­mercury(II)

Ahmad, S.; Sadaf, H.; Akkurt, M.; Sharif, S.; Khan, I.U.

doi:10.1107/S1600536809035594

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1191-m1192

doi:10.1107/S1600536809035594

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Bis(1,3-dibutylthiourea)dicyanidomercury(II)

Saeed Ahmad,^a ^* Haseeba Sadaf,^a Mehmet Akkurt,^b ^* Shahzad Sharif ^c and Islam Ullah Khan ^c

^aDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: saeed_a786@hotmail.com, akkurt@erciyes.edu.tr

(Received 2 September 2009; accepted 3 September 2009; online 9 September 2009)

In the title compound, [Hg(CN)₂(C₉H₂₀N₂S)₂], the Hg atom lies on a twofold rotation axis. There is only half a molecule in the asymmetric unit. The Hg atom has a distorted tetrahedral coordination involving the S atoms of two 1-butyl-3-propylthiourea groups and the C atoms of the two CN⁻ anions. In the crystal packing, adjacent molecules are connected by intermolecular N—H⋯N and N—H⋯S hydrogen bonds, forming infinite chains in three dimensions.

Related literature

For the coordination chemistry of thiourea-type ligands, see: Nadeem et al. (2009 , 2008 ); Zoufalá et al. (2007 ); Khan et al. (2007 ); Hanif et al. (2007 ); Fuks et al. (2005 ); Moro et al. (2009 ); Matesanz & Souza (2007 ). For crystallographic reports about mercury(II) complexes containing thioamides, see: Popovic et al. (2000 , 2002 ); Pavlović et al. (2000 ); Jiang et al. (2001 ); Wu et al. (2004 ). For the spectroscopy and structural chemistry of cyanide complexes of silver(I) and gold(I) with thiones, see: Hanif et al. (2007); Wu et al. (2004); Ahmad, Isab & Ashraf (2002 ); Ahmad, Isab & Perzanowski (2002 ); Ashraf et al. (2002 ); Ahmad & Isab (2001 ); Ahmad (2004 ).

Experimental

Crystal data

[Hg(CN)₂(C₉H₂₀N₂S)₂]
M_r = 629.31
Monoclinic, C 2/c
a = 17.4692 (3) Å
b = 9.5928 (2) Å
c = 17.4699 (4) Å
β = 111.540 (1)°
V = 2723.12 (10) Å³
Z = 4
Mo Kα radiation
μ = 5.82 mm⁻¹
T = 296 K
0.14 × 0.15 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: none
15120 measured reflections
3372 independent reflections
2918 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.044
S = 1.02
3372 reflections
134 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1ⁱ	0.86	2.68	3.479 (2)	155
N3—H3⋯N1ⁱⁱ	0.86	2.20	2.991 (3)	153
C7—H7B⋯S1	0.97	2.67	3.070 (3)	105
Symmetry codes: (i) $[-x+2, y, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035594/bt5052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035594/bt5052Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of thiourea type ligands has been the subject of several recent studies because of the relevance of their binding sites to those in living systems (Nadeem et al., 2009; Nadeem et al., 2008; Zoufalá et al., 2007; Khan et al., 2007; Hanif et al., 2007; Fuks et al., 2005; Moro et al., 2009; Matesanz & Souza, 2007). Crystallographic reports about mercury (II) complexes containing thioamides establish that these ligands are coordinated via the sulfur atom(Popovic et al., 2000, 2002; Pavlović, Popović, Soldin et al., 2000; Jiang et al., 2001; Wu et al., 2004). We have been involved in investigating the spectral and structural chemistry of cyanido complexes of silver (I) and gold (I) with thiones with emphasis onligand scrambling reactions (Hanif et al., 2007; Wu et al., 2004; Ahmad, Isab & Ashraf, 2002; Ahmad, Isab & Perzanowski, 2002; Ashraf et al., 2002; Ahmad & Isab, 2001; Ahmad, 2004). As a part ofextension of our work towards complexation of Hg (CN)₂ with thiones, we report here the crystal structures of [(N,N^/-dibutylthiourea)₂Hg(CN)₂], (I).

In the title compound (I), (Fig. 1), the Hg anion lies on a twofold rotation axes paralel to the b axis in space group C2/c and one half of the molecule to the other half are connected by this symmetry operation. The Hg atom has a distorted tetrahedral coordination by the S atoms of two N,N^/-dibutylthiourea groups and the C atoms of the two CN groups. The bond distances Hg—S and Hg—C are 2.7424 (7) Å and 2.072 (3) Å, and the bond angles C—Hg—C, S—Hg—S and C—Hg—C are 150.51 (11)°, 95.55 (2)° and 100.45 (8)°. All bond lengths and bond angles in (I) are in the range of expected values.

In the crystal packing, the adjacent molecules are connected by intermolecular N—H···N and N—H···S hydrogen bonds (Table 1). In Fig. 2, the packing and hydrogen bonding of (I) are shown viewed down b axis.

Related literature top

For the coordination chemistry of thiourea-type ligands, see: Nadeem et al. (2009, 2008); Zoufalá et al. (2007); Khan et al. (2007); Hanif et al. (2007); Fuks et al. (2005); Moro et al. (2009); Matesanz & Souza (2007). For crystallographic reports about mercury(II) complexes containing thioamides, see: Popovic et al. (2000, 2002); Pavlović et al. (2000); Jiang et al. (2001); Wu et al. (2004). For the spectral and structural chemistry of cyanide complexes of silver(I) and gold(I) with thiones, see: Hanif et al. (2007); Wu et al. (2004); Ahmad, Isab & Ashraf (2002); Ahmad, Isab & Perzanowski (2002); Ashraf et al. (2002); Ahmad & Isab (2001); Ahmad (2004).

Experimental top

For the preparation of the title complex, Hg (CN)₂ was prepared first by the reaction of 1 mmol HgCl₂ in methanol with 2 mmole of KCN in water. Then 0.253 g (1 mmole) Hg (CN)₂ dissolved in15 ml methanol was mixed with 2 equivalents of N,N^/-dibutylthiourea in 15 methanol. After stirring for 15 minutes, the resulting mixture was filtered and filtrate was kept at room temperature. After 24 h white crystals were obtained.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding of (I) viewed down b axis. Hydrogen atoms not involved in the showed interactions have been omitted for clarity.

Bis(1,3-dibutylthiourea)dicyanidomercury(II) top

Crystal data top

[Hg(CN)₂(C₉H₂₀N₂S)₂]	F(000) = 1256
M_r = 629.31	D_x = 1.535 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6609 reflections
a = 17.4692 (3) Å	θ = 2.5–27.2°
b = 9.5928 (2) Å	µ = 5.82 mm⁻¹
c = 17.4699 (4) Å	T = 296 K
β = 111.540 (1)°	Irregular, white
V = 2723.12 (10) Å³	0.17 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2918 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 2.5°
ϕ and ω scans	h = −23→23
15120 measured reflections	k = −12→12
3372 independent reflections	l = −20→23

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.044	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0211P)²], where P = (F_o² + 2F_c²)/3
3372 reflections	(Δ/σ)_max = 0.001
134 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Hg(CN)₂(C₉H₂₀N₂S)₂]	V = 2723.12 (10) Å³
M_r = 629.31	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.4692 (3) Å	µ = 5.82 mm⁻¹
b = 9.5928 (2) Å	T = 296 K
c = 17.4699 (4) Å	0.17 × 0.15 × 0.14 mm
β = 111.540 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2918 reflections with I > 2σ(I)
15120 measured reflections	R_int = 0.032
3372 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.044	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
3372 reflections	Δρ_min = −0.72 e Å⁻³
134 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Hg1	1.00000	0.20478 (1)	0.75000	0.0405 (1)
S1	1.08516 (3)	0.39691 (7)	0.86634 (4)	0.0414 (2)
N1	0.86048 (15)	0.1224 (3)	0.81955 (17)	0.0718 (10)
N2	1.11488 (12)	0.5094 (2)	0.74219 (12)	0.0422 (7)
N3	1.22801 (11)	0.4758 (2)	0.85840 (12)	0.0411 (7)
C1	0.91098 (16)	0.1498 (3)	0.79668 (17)	0.0475 (9)
C2	1.14750 (13)	0.4655 (2)	0.81878 (15)	0.0341 (7)
C3	1.16093 (17)	0.5591 (3)	0.69240 (17)	0.0548 (10)
C4	1.10347 (17)	0.6051 (3)	0.60900 (17)	0.0534 (10)
C5	1.0548 (2)	0.7334 (4)	0.6094 (2)	0.0633 (12)
C6	0.9979 (3)	0.7767 (4)	0.5243 (3)	0.0875 (17)
C7	1.27223 (15)	0.4387 (3)	0.94375 (16)	0.0441 (8)
C8	1.27906 (17)	0.5571 (3)	1.00242 (16)	0.0473 (9)
C9	1.3311 (2)	0.5232 (3)	1.09034 (17)	0.0586 (11)
C10	1.3434 (3)	0.6466 (4)	1.1477 (2)	0.0795 (14)
H2	1.06210	0.50880	0.71950	0.0510*
H3	1.25650	0.50710	0.83120	0.0490*
H3A	1.19600	0.48500	0.68630	0.0660*
H3B	1.19580	0.63660	0.72020	0.0660*
H4A	1.13530	0.62230	0.57470	0.0640*
H4B	1.06550	0.52970	0.58410	0.0640*
H5A	1.09240	0.80930	0.63420	0.0760*
H5B	1.02240	0.71650	0.64330	0.0760*
H6A	1.02880	0.78550	0.48910	0.1310*
H6B	0.97300	0.86460	0.52750	0.1310*
H6C	0.95580	0.70750	0.50240	0.1310*
H7A	1.32710	0.40780	0.95010	0.0530*
H7B	1.24430	0.36120	0.95810	0.0530*
H8A	1.22430	0.58250	0.99950	0.0570*
H8B	1.30250	0.63730	0.98510	0.0570*
H9A	1.38450	0.49040	1.09270	0.0700*
H9B	1.30520	0.44820	1.10920	0.0700*
H10A	1.36760	0.72220	1.12850	0.1190*
H10B	1.37910	0.62040	1.20210	0.1190*
H10C	1.29110	0.67540	1.14870	0.1190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0323 (1)	0.0459 (1)	0.0478 (1)	0.0000	0.0199 (1)	0.0000
S1	0.0359 (3)	0.0566 (4)	0.0340 (3)	−0.0115 (3)	0.0154 (3)	−0.0005 (3)
N1	0.0516 (14)	0.104 (2)	0.0668 (17)	−0.0297 (15)	0.0300 (13)	−0.0046 (17)
N2	0.0326 (10)	0.0594 (14)	0.0352 (12)	−0.0068 (9)	0.0133 (9)	0.0057 (11)
N3	0.0313 (10)	0.0545 (13)	0.0383 (12)	−0.0043 (9)	0.0136 (9)	0.0051 (10)
C1	0.0385 (13)	0.0553 (16)	0.0463 (16)	−0.0125 (12)	0.0126 (12)	−0.0037 (14)
C2	0.0330 (11)	0.0369 (13)	0.0340 (14)	−0.0030 (9)	0.0142 (10)	−0.0015 (11)
C3	0.0473 (15)	0.076 (2)	0.0491 (17)	−0.0018 (14)	0.0270 (14)	0.0144 (15)
C4	0.0563 (16)	0.069 (2)	0.0396 (16)	−0.0019 (14)	0.0232 (13)	0.0039 (15)
C5	0.076 (2)	0.066 (2)	0.052 (2)	0.0065 (17)	0.0285 (17)	0.0103 (16)
C6	0.084 (3)	0.101 (3)	0.074 (3)	0.026 (2)	0.025 (2)	0.020 (2)
C7	0.0353 (12)	0.0476 (15)	0.0446 (16)	0.0040 (11)	0.0089 (11)	0.0054 (13)
C8	0.0477 (14)	0.0466 (15)	0.0427 (16)	0.0038 (12)	0.0110 (12)	0.0064 (13)
C9	0.0665 (19)	0.0565 (19)	0.0433 (17)	0.0044 (15)	0.0090 (15)	0.0050 (15)
C10	0.107 (3)	0.066 (2)	0.051 (2)	−0.005 (2)	0.012 (2)	−0.0008 (19)

Geometric parameters (Å, º) top

Hg1—S1	2.7424 (7)	C3—H3A	0.9700
Hg1—C1	2.072 (3)	C3—H3B	0.9700
Hg1—S1ⁱ	2.7424 (7)	C4—H4A	0.9700
Hg1—C1ⁱ	2.072 (3)	C4—H4B	0.9700
S1—C2	1.724 (2)	C5—H5A	0.9700
N1—C1	1.125 (4)	C5—H5B	0.9700
N2—C2	1.316 (3)	C6—H6A	0.9600
N2—C3	1.465 (4)	C6—H6B	0.9600
N3—C2	1.324 (3)	C6—H6C	0.9600
N3—C7	1.449 (3)	C7—H7A	0.9700
N2—H2	0.8600	C7—H7B	0.9700
N3—H3	0.8600	C8—H8A	0.9700
C3—C4	1.500 (4)	C8—H8B	0.9700
C4—C5	1.497 (5)	C9—H9A	0.9700
C5—C6	1.512 (6)	C9—H9B	0.9700
C7—C8	1.505 (4)	C10—H10A	0.9600
C8—C9	1.505 (4)	C10—H10B	0.9600
C9—C10	1.514 (5)	C10—H10C	0.9600

S1···C1	3.693 (3)	H3A···N3	2.8500
S1···C8	3.684 (3)	H3A···H3	2.3700
S1···N2ⁱ	3.479 (2)	H3A···H10C^vi	2.5200
S1···H7B	2.6700	H3B···N3	2.7400
S1···H2ⁱ	2.6800	H3B···H3	2.2200
S1···H6Aⁱⁱ	3.1900	H3B···H5A	2.5000
N1···N3ⁱⁱⁱ	2.991 (3)	H3B···N1^iv	2.7600
N1···C3ⁱⁱⁱ	3.431 (4)	H4A···H6A	2.4700
N2···S1ⁱ	3.479 (2)	H4B···H2	2.4000
N3···N1^iv	2.991 (3)	H4B···H6C	2.5700
N1···H3Bⁱⁱⁱ	2.7600	H5A···H3B	2.5000
N1···H3ⁱⁱⁱ	2.2000	H5A···H7A^vii	2.5600
N2···H5B	2.7400	H5B···N2	2.7400
N3···H3A	2.8500	H5B···H2	2.3500
N3···H3B	2.7400	H6A···H4A	2.4700
C1···S1	3.693 (3)	H6A···S1^vi	3.1900
C1···C2ⁱ	3.574 (4)	H6C···H4B	2.5700
C3···N1^iv	3.431 (4)	H7A···H9A	2.4500
C8···S1	3.684 (3)	H7A···H5A^viii	2.5600
C1···H10B^v	3.0100	H7B···S1	2.6700
C3···H3	2.4400	H7B···H9B	2.6000
C5···H2	2.8600	H7B···H7B^ix	2.5500
H2···C5	2.8600	H8A···H10C	2.5900
H2···H4B	2.4000	H8B···H10A	2.4800
H2···H5B	2.3500	H9A···H7A	2.4500
H2···S1ⁱ	2.6800	H9B···H7B	2.6000
H3···C3	2.4400	H10A···H8B	2.4800
H3···H3A	2.3700	H10B···C1^x	3.0100
H3···H3B	2.2200	H10C···H8A	2.5900
H3···N1^iv	2.2000	H10C···H3Aⁱⁱ	2.5200

S1—Hg1—C1	99.25 (8)	C4—C5—H5A	109.00
S1—Hg1—S1ⁱ	95.55 (2)	C4—C5—H5B	109.00
S1—Hg1—C1ⁱ	100.45 (8)	C6—C5—H5A	109.00
S1ⁱ—Hg1—C1	100.45 (8)	C6—C5—H5B	109.00
C1—Hg1—C1ⁱ	150.51 (11)	H5A—C5—H5B	108.00
S1ⁱ—Hg1—C1ⁱ	99.25 (8)	C5—C6—H6A	109.00
Hg1—S1—C2	99.56 (8)	C5—C6—H6B	109.00
C2—N2—C3	125.5 (2)	C5—C6—H6C	109.00
C2—N3—C7	125.6 (2)	H6A—C6—H6B	109.00
C2—N2—H2	117.00	H6A—C6—H6C	110.00
C3—N2—H2	117.00	H6B—C6—H6C	109.00
C2—N3—H3	117.00	N3—C7—H7A	109.00
C7—N3—H3	117.00	N3—C7—H7B	109.00
Hg1—C1—N1	177.4 (3)	C8—C7—H7A	109.00
S1—C2—N2	119.84 (19)	C8—C7—H7B	109.00
S1—C2—N3	120.95 (18)	H7A—C7—H7B	108.00
N2—C2—N3	119.2 (2)	C7—C8—H8A	109.00
N2—C3—C4	110.8 (2)	C7—C8—H8B	109.00
C3—C4—C5	114.6 (2)	C9—C8—H8A	109.00
C4—C5—C6	113.0 (3)	C9—C8—H8B	109.00
N3—C7—C8	113.2 (2)	H8A—C8—H8B	108.00
C7—C8—C9	113.5 (2)	C8—C9—H9A	109.00
C8—C9—C10	113.1 (3)	C8—C9—H9B	109.00
N2—C3—H3A	109.00	C10—C9—H9A	109.00
N2—C3—H3B	109.00	C10—C9—H9B	109.00
C4—C3—H3A	109.00	H9A—C9—H9B	108.00
C4—C3—H3B	109.00	C9—C10—H10A	109.00
H3A—C3—H3B	108.00	C9—C10—H10B	109.00
C3—C4—H4A	109.00	C9—C10—H10C	109.00
C3—C4—H4B	109.00	H10A—C10—H10B	110.00
C5—C4—H4A	109.00	H10A—C10—H10C	109.00
C5—C4—H4B	109.00	H10B—C10—H10C	110.00
H4A—C4—H4B	108.00

C1—Hg1—S1—C2	−169.87 (11)	C7—N3—C2—S1	−2.8 (3)
S1ⁱ—Hg1—S1—C2	−68.30 (8)	C7—N3—C2—N2	176.7 (2)
C1ⁱ—Hg1—S1—C2	32.19 (11)	C2—N3—C7—C8	−88.9 (3)
Hg1—S1—C2—N2	51.24 (18)	N2—C3—C4—C5	67.9 (3)
Hg1—S1—C2—N3	−129.28 (17)	C3—C4—C5—C6	179.8 (3)
C3—N2—C2—S1	−174.74 (19)	N3—C7—C8—C9	−175.0 (2)
C3—N2—C2—N3	5.8 (3)	C7—C8—C9—C10	175.2 (3)
C2—N2—C3—C4	−178.1 (2)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) x, −y+1, z+1/2; (iii) x−1/2, y−1/2, z; (iv) x+1/2, y+1/2, z; (v) x−1/2, −y+1/2, z−1/2; (vi) x, −y+1, z−1/2; (vii) −x+5/2, y+1/2, −z+3/2; (viii) −x+5/2, y−1/2, −z+3/2; (ix) −x+5/2, −y+1/2, −z+2; (x) x+1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.86	2.68	3.479 (2)	155
N3—H3···N1^iv	0.86	2.20	2.991 (3)	153
C7—H7B···S1	0.97	2.67	3.070 (3)	105

Symmetry codes: (i) −x+2, y, −z+3/2; (iv) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Hg(CN)₂(C₉H₂₀N₂S)₂]
M_r	629.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.4692 (3), 9.5928 (2), 17.4699 (4)
β (°)	111.540 (1)
V (Å³)	2723.12 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.82
Crystal size (mm)	0.17 × 0.15 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15120, 3372, 2918
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.044, 1.02
No. of reflections	3372
No. of parameters	134
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.72

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.8600	2.6800	3.479 (2)	155.00
N3—H3···N1ⁱⁱ	0.8600	2.2000	2.991 (3)	153.00
C7—H7B···S1	0.9700	2.6700	3.070 (3)	105.00

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) x+1/2, y+1/2, z.

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Volume 65| Part 10| October 2009| Pages m1191-m1192

doi:10.1107/S1600536809035594

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