4-Chloro-N-[N-(6-methyl-2-pyrid­yl)car­bamo­thio­yl]benzamide

Binzet, G.; Emen, F.M.; Flörke, U.; Yeşilkaynak, T.; Külcü, N.; Arslan, H.

doi:10.1107/S1600536808041123

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o81-o82

doi:10.1107/S1600536808041123

Open

access

4-Chloro-N-[N-(6-methyl-2-pyridyl)carbamothioyl]benzamide

Gün Binzet,^a Fatih Mehmet Emen,^a Ulrich Flörke,^b Tuncay Yeşilkaynak,^a Nevzat Külcü ^a and Hakan Arslan ^c,^d ^*

^aDepartment of Chemistry, Faculty of Arts and Science, Mersin University, 33343 Mersin, Turkey, ^bDepartment of Chemistry, University of Paderborn, 33098 Paderborn, Germany, ^cDepartment of Natural Sciences, Fayetteville State University, Fayetteville, NC, 28301, USA, and ^dDepartment of Chemistry, Faculty of Pharmacy, Mersin University, 33169 Mersin, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 10 November 2008; accepted 5 December 2008; online 10 December 2008)

In the title compound, C₁₄H₁₂ClN₃OS, the short exocyclic N—C bond lengths indicate resonance in the thiourea part of the molecule. The title compound is stabilized by an intramolecular N—H⋯N hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thiocarbonyl group and the pyridine group. Intermolecular N—H⋯S and C—H⋯O interactions are also present.

Related literature

For the synthesis, see: Mansuroğlu et al. (2008 ); Arslan et al. (2003a ,b ); Binzet et al. (2006 ). For general background, see: Arslan et al. (2006a ,b , 2007 ); Kemp et al. (1997 ); Koch et al. (1995 ); Nencki (1873 ); Özpozan et al. (2000 ). For related compounds, see: Arslan et al. (2003a, 2006b, 2007); Dong et al. (2008 ); Duque et al. (2008 ); Tutughamiarso & Bolte (2007 ); Yue et al. (2008 ); Yusof et al. (2008a ,b ); Xian (2008 ); Thiam et al. (2008 ); Binzet et al. (2006); Uğur et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₂ClN₃OS
M_r = 305.78
Triclinic, $[P \overline 1]$
a = 8.255 (3) Å
b = 9.030 (3) Å
c = 9.957 (3) Å
α = 80.810 (7)°
β = 66.552 (7)°
γ = 87.269 (7)°
V = 672.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 120 (2) K
0.20 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.918, T_max = 0.958
3651 measured reflections
2609 independent reflections
1492 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.266
S = 0.98
2609 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.95	2.42	3.303 (7)	154
N2—H2B⋯S1ⁱⁱ	0.88	2.61	3.464 (5)	165
N1—H1B⋯N3	0.88	1.90	2.651 (7)	142
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041123/hg2444sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041123/hg2444Isup2.hkl

checkCIF report

Comment top

Thiourea derivatives, first synthesized by Nencki, 1873, are very flexible ligands and able to coordinate to a range of metal centers as neutral ligands, monoanions or dianions (Mansuroğlu et al., 2008; Arslan et al., 2003b, 2006a; Binzet et al., 2006; Kemp et al., 1997; Koch et al., 1995). In addition, the oxygen, nitrogen and sulfur donors provide a multitude of bonding possibilities. The coordination chemistry of substituted thioureas has led to some interesting practical applications such as liquid–liquid extraction, pre-concentration and highly efficient chromatographic separation (Kemp et al., 1997; Koch et al., 1995).

Our team focused on the synthesis, characterization, crystal structure, thermal behavior and antimicrobial activity of new thiourea derivatives (Mansuroğlu et al., 2008; Arslan et al., 2003a, 2003b, 2006a, 2006b, 2007; Uğur et al., 2006; Özpozan et al., 2000). In this article, we report the preparation and characterization of a novel thiourea compound, 4-chloro-N-(6-methylpyridin-2-yl-carbamothioyl)benzamide (I), and its crystal structure. The title compound was purified by re-crystallization from ethanol:dichloromethane mixture (1:2) and characterized by elemental analysis. The analytical data is consistent with the proposed structure given in Scheme 1.

The molecular structure and packing diagram are depicted in Figure 1 and 2, respectively. The bond lengths and angles in the thiourea moiety are typical for thiourea derivatives; the C8—S1 and C7—O1 bonds both show a typical double-bond character with 1.655 (5) and 1.203 (6) Å, respectively. The short bond lengths of the N1—C7, 1.395 (7); N1—C8, 1.376 (6) and N2—C8, 1.364 (6) Å bonds indicate partial double bond character. These results can be explained by the existence of resonance in this part of the molecule. The other C—N bond length is within the expected range.

A lot of substitute benzoylthiourea derivatives have cis-trans configurations (Yusof, et al., 2008a, 2008b; Thiam, et al., 2008; Xian, 2008; Dong, et al., 2008; Duque, et al., 2008). However, the title compound shows an intramolecular N—H···N hydrogen bond (Table 1) which results in the formation of a six membered ring (N3—C9—N2—C8—N1—H1) and leads to a syn-periplanar conformation between the thiocarbonyl group carbon atom and the pyridine group nitrogen atom (Tutughamiarso & Bolte, 2007; Yue et al., 2008). The torsion angles in this region, C8—N2—C9—N3, 14.9 (9)° and C9—N2—C8—N1, -7.2 (8)° confirm this conformation. This formation forces the two amide hydrogen atoms to the opposite direction.

The carbonyl and thiocarbonyl part is essentially planar, as reflected by the torsional angles O1—C7—N1—C8, C7—N1—C8—S1 and C7—N1—C8—N2 of 1.7 (9), 0.3 (8) and 179.3 (5) °, respectively. O1, C7, N1, C8 and S1 fragment is also planar (maximum and mean deviations are 0.010 and 0.005 Å, respectively).

The crystal packing is shown in Fig. 2. There are two intermolecular, N—H···S and C—H···O, hydrogen bonds which connect molecules in chains parallel to [100].

Related literature top

For the synthesis, see: Mansuroğlu et al. (2008); Arslan et al. (2003a,b); Binzet et al. (2006). For general background, see: Arslan et al. (2006a,b, 2007); Kemp et al. (1997); Koch et al. (1995); Nencki (1873); Özpozan et al. (2000). For related compounds, see: Arslan et al. (2003a, 2006b, 2007); Dong et al. (2008); Duque et al. (2008); Tutughamiarso & Bolte (2007); Yue et al. (2008); Yusof et al. (2008a,b); Xian (2008); Thiam et al. (2008); Binzet et al. (2006); Uğur et al. (2006).

Experimental top

The compound was prepared with a procedure similar to that reported in the literature (Arslan et al., 2003b, 2006a). A solution of 4-chloro-benzoyl chloride (0.01 mol) in acetone (50 cm³) was added dropwise to a suspension of potassium thiocyanate (0.01 mol) in acetone (30 cm³). The reaction mixture was heated under reflux for 30 min, and then cooled to room temperature. A solution of 6-methylpyridin-2-amine (0.01 mol) in acetone (10 cm³) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 cm³) was added to the solution, which was then filtered. The solid product was washed with water and purifed by recrystalization from an ethanol:dichloromethane mixture (1:2). Anal. Calcd. for C₁₄H₁₂ClN₃OS: C, 55.0; H, 4.0; N, 13.7. Found: C, 55.1; H, 3.9; N, 13.7%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram for (I) viewed along a-direction. Hydrogen bonds shown as dotted lines.

4-Chloro-N-[N-(6-methyl-2-pyridyl)carbamothioyl]benzamide top

Crystal data top

C₁₄H₁₂ClN₃OS	Z = 2
M_r = 305.78	F(000) = 316
Triclinic, P1	D_x = 1.511 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.255 (3) Å	Cell parameters from 716 reflections
b = 9.030 (3) Å	θ = 2.3–26.3°
c = 9.957 (3) Å	µ = 0.44 mm⁻¹
α = 80.810 (7)°	T = 120 K
β = 66.552 (7)°	Prism, yellow
γ = 87.269 (7)°	0.20 × 0.14 × 0.10 mm
V = 672.1 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Radiation source: sealed tube	1492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.918, T_max = 0.958	k = −11→5
3651 measured reflections	l = −12→10

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.266	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.1601P)²] where P = (F_o² + 2F_c²)/3
2609 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₄H₁₂ClN₃OS	γ = 87.269 (7)°
M_r = 305.78	V = 672.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.255 (3) Å	Mo Kα radiation
b = 9.030 (3) Å	µ = 0.44 mm⁻¹
c = 9.957 (3) Å	T = 120 K
α = 80.810 (7)°	0.20 × 0.14 × 0.10 mm
β = 66.552 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1492 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.958	R_int = 0.100
3651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.266	H-atom parameters constrained
S = 0.98	Δρ_max = 0.81 e Å⁻³
2609 reflections	Δρ_min = −0.50 e Å⁻³
182 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
Cl1	−0.0760 (2)	−0.08311 (16)	0.24521 (19)	0.0469 (5)
S1	0.4068 (2)	0.83271 (15)	0.20068 (15)	0.0316 (5)
O1	0.2334 (6)	0.5331 (4)	0.3623 (4)	0.0370 (10)
N1	0.2869 (6)	0.6040 (5)	0.1158 (5)	0.0296 (11)
H1B	0.2730	0.5725	0.0418	0.036*
N2	0.4090 (6)	0.8104 (5)	−0.0583 (5)	0.0282 (11)
H2B	0.4462	0.9040	−0.0760	0.034*
N3	0.3162 (6)	0.6306 (5)	−0.1620 (5)	0.0253 (10)
C1	0.0432 (8)	0.2777 (6)	0.3757 (6)	0.0347 (14)
H1A	0.0183	0.3141	0.4662	0.042*
C2	−0.0314 (8)	0.1427 (6)	0.3760 (7)	0.0394 (15)
H2A	−0.1122	0.0888	0.4661	0.047*
C3	0.0122 (8)	0.0878 (6)	0.2450 (6)	0.0322 (13)
C4	0.1259 (8)	0.1664 (6)	0.1110 (6)	0.0365 (15)
H4A	0.1537	0.1280	0.0211	0.044*
C5	0.1987 (7)	0.3030 (6)	0.1107 (6)	0.0264 (12)
H5A	0.2783	0.3572	0.0201	0.032*
C6	0.1558 (7)	0.3597 (5)	0.2407 (6)	0.0258 (12)
C7	0.2278 (7)	0.5061 (6)	0.2497 (6)	0.0272 (12)
C8	0.3644 (6)	0.7438 (5)	0.0850 (6)	0.0208 (11)
C9	0.4067 (7)	0.7576 (6)	−0.1828 (6)	0.0261 (12)
C10	0.5010 (7)	0.8375 (6)	−0.3213 (6)	0.0291 (13)
H10A	0.5701	0.9232	−0.3321	0.035*
C11	0.4925 (8)	0.7902 (6)	−0.4435 (6)	0.0316 (13)
H11A	0.5503	0.8463	−0.5394	0.038*
C12	0.3987 (7)	0.6598 (6)	−0.4245 (6)	0.0287 (13)
H12A	0.3913	0.6251	−0.5071	0.034*
C13	0.3156 (7)	0.5806 (6)	−0.2823 (6)	0.0229 (12)
C14	0.2159 (8)	0.4360 (6)	−0.2553 (7)	0.0322 (13)
H14A	0.2846	0.3515	−0.2327	0.048*
H14B	0.1965	0.4249	−0.3441	0.048*
H14C	0.1018	0.4375	−0.1715	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0577 (11)	0.0250 (8)	0.0548 (11)	−0.0248 (7)	−0.0183 (9)	−0.0001 (7)
S1	0.0473 (10)	0.0223 (7)	0.0274 (8)	−0.0173 (6)	−0.0164 (7)	−0.0004 (6)
O1	0.053 (3)	0.030 (2)	0.029 (2)	−0.0182 (19)	−0.017 (2)	−0.0027 (17)
N1	0.043 (3)	0.023 (2)	0.022 (2)	−0.019 (2)	−0.009 (2)	−0.0055 (19)
N2	0.038 (3)	0.020 (2)	0.027 (2)	−0.0162 (19)	−0.013 (2)	−0.0017 (18)
N3	0.024 (2)	0.022 (2)	0.034 (3)	−0.0071 (18)	−0.015 (2)	−0.0014 (19)
C1	0.059 (4)	0.022 (3)	0.019 (3)	−0.015 (3)	−0.012 (3)	0.004 (2)
C2	0.045 (4)	0.027 (3)	0.034 (3)	−0.022 (3)	−0.003 (3)	0.003 (3)
C3	0.040 (3)	0.022 (3)	0.029 (3)	−0.019 (2)	−0.009 (3)	0.005 (2)
C4	0.064 (4)	0.021 (3)	0.024 (3)	−0.014 (3)	−0.017 (3)	0.001 (2)
C5	0.033 (3)	0.020 (3)	0.026 (3)	−0.013 (2)	−0.015 (2)	0.007 (2)
C6	0.030 (3)	0.017 (3)	0.030 (3)	−0.008 (2)	−0.013 (3)	0.004 (2)
C7	0.035 (3)	0.020 (3)	0.027 (3)	−0.009 (2)	−0.015 (3)	0.002 (2)
C8	0.020 (3)	0.017 (2)	0.029 (3)	0.000 (2)	−0.016 (2)	0.004 (2)
C9	0.043 (3)	0.017 (3)	0.020 (3)	−0.009 (2)	−0.016 (3)	0.004 (2)
C10	0.036 (3)	0.020 (3)	0.032 (3)	−0.013 (2)	−0.015 (3)	0.003 (2)
C11	0.047 (4)	0.020 (3)	0.024 (3)	−0.013 (2)	−0.011 (3)	0.001 (2)
C12	0.036 (3)	0.025 (3)	0.024 (3)	−0.014 (2)	−0.010 (2)	−0.004 (2)
C13	0.027 (3)	0.021 (3)	0.026 (3)	−0.004 (2)	−0.016 (2)	0.001 (2)
C14	0.042 (3)	0.024 (3)	0.038 (3)	−0.011 (2)	−0.022 (3)	−0.006 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.737 (5)	C4—C5	1.396 (7)
S1—C8	1.655 (5)	C4—H4A	0.9500
O1—C7	1.203 (6)	C5—C6	1.376 (7)
N1—C8	1.376 (6)	C5—H5A	0.9500
N1—C7	1.395 (7)	C6—C7	1.504 (7)
N1—H1B	0.8800	C9—C10	1.382 (7)
N2—C8	1.364 (6)	C10—C11	1.379 (7)
N2—C9	1.405 (6)	C10—H10A	0.9500
N2—H2B	0.8800	C11—C12	1.386 (7)
N3—C9	1.341 (6)	C11—H11A	0.9500
N3—C13	1.347 (7)	C12—C13	1.392 (7)
C1—C2	1.391 (7)	C12—H12A	0.9500
C1—C6	1.405 (7)	C13—C14	1.506 (7)
C1—H1A	0.9500	C14—H14A	0.9800
C2—C3	1.375 (8)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C3—C4	1.390 (8)

C8—N1—C7	128.0 (4)	O1—C7—C6	122.3 (5)
C8—N1—H1B	116.0	N1—C7—C6	113.2 (4)
C7—N1—H1B	116.0	N2—C8—N1	113.5 (4)
C8—N2—C9	132.1 (4)	N2—C8—S1	119.5 (4)
C8—N2—H2B	113.9	N1—C8—S1	127.1 (4)
C9—N2—H2B	113.9	N3—C9—C10	123.1 (5)
C9—N3—C13	118.0 (5)	N3—C9—N2	118.5 (5)
C2—C1—C6	119.5 (5)	C10—C9—N2	118.3 (5)
C2—C1—H1A	120.2	C11—C10—C9	118.6 (5)
C6—C1—H1A	120.2	C11—C10—H10A	120.7
C3—C2—C1	119.7 (5)	C9—C10—H10A	120.7
C3—C2—H2A	120.2	C10—C11—C12	119.2 (5)
C1—C2—H2A	120.2	C10—C11—H11A	120.4
C2—C3—C4	121.4 (5)	C12—C11—H11A	120.4
C2—C3—Cl1	119.9 (4)	C11—C12—C13	118.8 (5)
C4—C3—Cl1	118.7 (4)	C11—C12—H12A	120.6
C3—C4—C5	118.8 (5)	C13—C12—H12A	120.6
C3—C4—H4A	120.6	N3—C13—C12	122.1 (5)
C5—C4—H4A	120.6	N3—C13—C14	116.7 (5)
C6—C5—C4	120.5 (5)	C12—C13—C14	121.2 (5)
C6—C5—H5A	119.8	C13—C14—H14A	109.5
C4—C5—H5A	119.8	C13—C14—H14B	109.5
C5—C6—C1	120.1 (5)	H14A—C14—H14B	109.5
C5—C6—C7	123.7 (5)	C13—C14—H14C	109.5
C1—C6—C7	116.2 (5)	H14A—C14—H14C	109.5
O1—C7—N1	124.4 (5)	H14B—C14—H14C	109.5

C6—C1—C2—C3	3.0 (10)	C9—N2—C8—N1	−7.2 (8)
C1—C2—C3—C4	−1.9 (10)	C9—N2—C8—S1	172.4 (5)
C1—C2—C3—Cl1	178.3 (5)	C7—N1—C8—N2	179.3 (5)
C2—C3—C4—C5	0.9 (10)	C7—N1—C8—S1	−0.3 (8)
Cl1—C3—C4—C5	−179.3 (4)	C13—N3—C9—C10	−1.1 (8)
C3—C4—C5—C6	−1.2 (9)	C13—N3—C9—N2	−179.7 (4)
C4—C5—C6—C1	2.3 (9)	C8—N2—C9—N3	14.9 (9)
C4—C5—C6—C7	−179.8 (5)	C8—N2—C9—C10	−163.8 (5)
C2—C1—C6—C5	−3.3 (9)	N3—C9—C10—C11	4.4 (9)
C2—C1—C6—C7	178.7 (5)	N2—C9—C10—C11	−177.0 (5)
C8—N1—C7—O1	1.7 (9)	C9—C10—C11—C12	−3.7 (8)
C8—N1—C7—C6	−177.9 (5)	C10—C11—C12—C13	0.1 (9)
C5—C6—C7—O1	−157.3 (6)	C9—N3—C13—C12	−2.8 (8)
C1—C6—C7—O1	20.7 (8)	C9—N3—C13—C14	178.7 (5)
C5—C6—C7—N1	22.3 (8)	C11—C12—C13—N3	3.3 (8)
C1—C6—C7—N1	−159.7 (5)	C11—C12—C13—C14	−178.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.42	3.303 (7)	154
N2—H2B···S1ⁱⁱ	0.88	2.61	3.464 (5)	165
N1—H1B···N3	0.88	1.90	2.651 (7)	142

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClN₃OS
M_r	305.78
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.255 (3), 9.030 (3), 9.957 (3)
α, β, γ (°)	80.810 (7), 66.552 (7), 87.269 (7)
V (Å³)	672.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.918, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	3651, 2609, 1492
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.266, 0.98
No. of reflections	2609
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.50

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.42	3.303 (7)	154
N2—H2B···S1ⁱⁱ	0.88	2.61	3.464 (5)	165
N1—H1B···N3	0.88	1.90	2.651 (7)	142

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

Acknowledgements

This work was supported by Mersin University Research Fund (Project Nos. BAP-ECZ-F-TBB-(HA) 2004–3 and BAP-FEF-KB-(NK) 2006–3).

References

Arslan, H., Flörke, U. & Külcü, N. (2003a). J. Chem. Crystallogr. 33, 919–924. Web of Science CSD CrossRef CAS Google Scholar
Arslan, H., Flörke, U. & Külcü, N. (2007). Spectrochim. Acta A, 67, 936–943. CSD CrossRef Google Scholar
Arslan, H., Flörke, U., Külcü, N. & Emen, M. F. (2006a). J. Coord. Chem. 59, 223–228. Web of Science CSD CrossRef CAS Google Scholar
Arslan, H., Külcü, N. & Flörke, U. (2003b). Transition Met. Chem. 28, 816–819. Web of Science CSD CrossRef CAS Google Scholar
Arslan, H., Külcü, N. & Flörke, U. (2006b). Spectrochim. Acta A, 64, 1065–1071. CrossRef Google Scholar
Binzet, G., Arslan, H., Flörke, U., Külcü, N. & Duran, N. (2006). J. Coord. Chem. 59, 1395–1406. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dong, W.-K., Yan, H.-B., Chai, L.-Q., Lv, Z.-W. & Zhao, C.-Y. (2008). Acta Cryst. E64, o1097. Web of Science CSD CrossRef IUCr Journals Google Scholar
Duque, J., Estevez-Hernandez, O., Reguera, E., Corrêa, R. S. & Gutierrez Maria, P. (2008). Acta Cryst. E64, o1068. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kemp, G., Roodt, A., Purcell, W. & Koch, K. R. (1997). J. Chem. Soc. Dalton Trans. 23, 4481–4483. Web of Science CSD CrossRef Google Scholar
Koch, K. R., Sacht, C., Grimmbacher, T. & Bourne, S. (1995). S. Afr. J. Chem. 48, 71–77. CAS Google Scholar
Mansuroğlu, D. S., Arslan, H., Flörke, U. & Külcü, N. (2008). J. Coord. Chem. 61, 3134–3146. Google Scholar
Nencki, M. (1873). Ber. Dtsch. Chem. Ges. 6, 598–600. CrossRef Google Scholar
Özpozan, N., Arslan, H., Ozpozan, T., Ozdes, N. & Külcü, N. (2000). Thermochim. Acta, 343, 127–133. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tutughamiarso, M. & Bolte, M. (2007). Acta Cryst. E63, o4682. Web of Science CSD CrossRef IUCr Journals Google Scholar
Uğur, D., Arslan, H. & Külcü, N. (2006). Russ. J. Coord. Chem. 32, 669–675. Google Scholar
Xian, L. (2008). Acta Cryst. E64, o1969. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yue, H., Wang, Y., Xia, A., Luo, S. & Xu, D. (2008). Acta Cryst. E64, o858. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yusof, M. S. M., Ayob, N. A. C., Kadir, M. A. & Yamin, B. M. (2008a). Acta Cryst. E64, o937. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yusof, M. S. M., Muharam, S. H., Kassim, M. B. & Yamin, B. M. (2008b). Acta Cryst. E64, o1137. Web of Science CSD CrossRef IUCr Journals Google Scholar