1-Cyclo­hexyl-3-{(E)-[1-(pyridin-2-yl)ethyl­idene]amino}­thio­urea

Salam, M.A.; Affan, M.A.; Ahmad, F.B.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811009317

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o955

doi:10.1107/S1600536811009317

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1-Cyclohexyl-3-{(E)-[1-(pyridin-2-yl)ethylidene]amino}thiourea

Md. Abdus Salam,^a Md. Abu Affan,^a ‡ Fasihuddin B. Ahmad,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 March 2011; accepted 11 March 2011; online 23 March 2011)

In the title thiourea derivative, C₁₄H₂₀N₄S, the non-ring non-H atoms are approximately planar, with an r.m.s. deviation of 0.0720 Å. The pyridine ring is twisted out of this plane and makes a dihedral angle of 16.85 (13)° with it. The mean plane passing through the cyclohexyl ring is almost normal to the central plane [dihedral angle = 69.23 (8)°]. An intramolecular N—H⋯N(imine) hydrogen bond occurs. Centrosymmetric dimers are formed in the crystal structure via pairs of N—H⋯S hydrogen bonds, and these are connected into a supramolecular chain along the a axis via C—H⋯π(pyridyl) interactions.

Related literature

For related thiourea structures, see: Tiekink (1989 ); Lai & Tiekink (2002 ); Muramulla et al. (2009 ).

Experimental

Crystal data

C₁₄H₂₀N₄S
M_r = 276.40
Triclinic, $[P \overline 1]$
a = 5.8824 (6) Å
b = 10.2410 (9) Å
c = 12.3902 (14) Å
α = 94.718 (8)°
β = 90.427 (9)°
γ = 90.979 (8)°
V = 743.74 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ) T_min = 0.842, T_max = 1.000
5817 measured reflections
3292 independent reflections
2355 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.151
S = 1.04
3292 reflections
181 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.87 (2)	2.16 (2)	2.592 (3)	111 (2)
N2—H2⋯S1ⁱ	0.88 (2)	2.73 (2)	3.610 (2)	174 (2)
C9—H9b⋯Cg1ⁱⁱ	0.96	2.89	3.776 (3)	155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009317/hg5008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009317/hg5008Isup2.hkl

checkCIF report

Comment top

In continuation of long-term structural investigations of thiourea derivatives (Tiekink, 1989; Lai & Tiekink, 2002; Muramulla et al., 2009), the title compound, (I), was investigated. The atoms comprising the thiosemicarbazone backbone of the molecules, i.e. S1,N1—N3,C1,C7—C10 are co-planar (r.m.s. = 0.0720 Å). While the pyridine residue is twisted out of this plane as seen in the value of the N3—C8—C10—N4 torsion angle of 164.7 (2) °, the cyclohexyl group is almost normal to the plane; C2—C1—N1—C7 is 87.7 (3) °. The amine-N—H1 and imine-N3 atoms are directed to the same side of the molecule enabling the formation of an intramolecular N—H···N hydrogen bond, Table 1. The pyridine-N atom is directed away from the rest of the molecule and is proximate to the methyl substituent which results in the formation of a C—H···N contact, Table 1.

The crystal packing is dominated by N—H···S hydrogen bonds that lead to centrosymmetric dimers, Table 1. Dimers aligned along the a axis are connected into a supramolecular chain via C—H···π interactions involving methyl-H and the pyridyl ring. There are no specific intermolecular interactions occurring between chains, Fig. 3.

Related literature top

For related thiourea structures, see: Tiekink (1989); Lai & Tiekink (2002); Muramulla et al. (2009).

Experimental top

Cyclohexyl isothiocyanate (0.706 g, 5 mmol) and hydrazine hydrate (0.250 g, 5 mmol), each dissolved in 10 ml ethanol, were mixed with constant stirring. The stirring was continued for 30 min and the white product, N(4)-cyclohexylthiosemicarbazide formed was washed with ethanol and dried. A solution of the N(4)-cyclohexylthiosemicarbazide (0.51 g, 3 mmol) in 10 ml methanol was refluxed with a methanolic solution of 2-acetylpyridine (0.363 g, 3 mmol) for 5 h after adding 1–2 drops of acetic acid. A white powder separated on cooling the solution which was filtered and washed with methanol. This was recrystallized from methanol and dried in vacuo over silica gel. (M.pt. 453–455 K; Yield 0.682 g, 76%). Elemental analysis: Calc.: C, 60.83; H, 7.29; N, 11.60%. Found: C, 60.72; H, 7.25; N, 11.57%. FT—IR (KBr, cm^-1) ν_max: 3329 (s, NH), 2931, 2851 (s, cyclohexyl), 1580 (w, C═N—N═C), 980 (m, N—N), 1358, 835 (w, C═ S), 657 (m, pyridine in plane).

Computing details top

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO (Agilent Technologies, 2010); data reduction: CrysAlis PRO (Agilent Technologies, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the supramolecular chain aligned along the a axis in (I). The N—H···S hydrogen bonds and C—H···π contacts are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the crystal packing in (I). The N—H···S hydrogen bonds and C—H···π contacts are shown as orange and purple dashed lines, respectively.

1-Cyclohexyl-3-{(E)-[1-(pyridin-2-yl)ethylidene]amino}thiourea top

Crystal data top

C₁₄H₂₀N₄S	Z = 2
M_r = 276.40	F(000) = 296
Triclinic, P1	D_x = 1.234 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8824 (6) Å	Cell parameters from 2234 reflections
b = 10.2410 (9) Å	θ = 2.5–29.3°
c = 12.3902 (14) Å	µ = 0.21 mm⁻¹
α = 94.718 (8)°	T = 295 K
β = 90.427 (9)°	Block, colourless
γ = 90.979 (8)°	0.25 × 0.20 × 0.15 mm
V = 743.74 (13) Å³

Data collection top

Agilent Supernova Dual diffractometer with an Atlas detector	3292 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2355 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −12→11
T_min = 0.842, T_max = 1.000	l = −16→15
5817 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0595P)² + 0.2389P] where P = (F_o² + 2F_c²)/3
3292 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₂₀N₄S	γ = 90.979 (8)°
M_r = 276.40	V = 743.74 (13) Å³
Triclinic, P1	Z = 2
a = 5.8824 (6) Å	Mo Kα radiation
b = 10.2410 (9) Å	µ = 0.21 mm⁻¹
c = 12.3902 (14) Å	T = 295 K
α = 94.718 (8)°	0.25 × 0.20 × 0.15 mm
β = 90.427 (9)°

Data collection top

Agilent Supernova Dual diffractometer with an Atlas detector	3292 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	2355 reflections with I > 2σ(I)
T_min = 0.842, T_max = 1.000	R_int = 0.027
5817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	2 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
3292 reflections	Δρ_min = −0.20 e Å⁻³
181 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
S1	0.98373 (10)	0.38035 (6)	0.62998 (5)	0.0566 (2)
N1	0.6028 (3)	0.4301 (2)	0.73985 (16)	0.0516 (5)
N2	0.6780 (3)	0.56047 (19)	0.60354 (16)	0.0473 (5)
N3	0.4954 (3)	0.63316 (18)	0.63973 (15)	0.0443 (4)
N4	0.2260 (4)	0.9312 (2)	0.61127 (19)	0.0655 (6)
C1	0.6423 (4)	0.3310 (2)	0.81548 (18)	0.0509 (6)
H1A	0.7317	0.2612	0.7785	0.061*
C2	0.7750 (5)	0.3871 (3)	0.9131 (2)	0.0774 (9)
H2A	0.6945	0.4610	0.9476	0.093*
H2B	0.9219	0.4189	0.8903	0.093*
C3	0.8102 (6)	0.2857 (4)	0.9947 (3)	0.1056 (13)
H3A	0.9038	0.2159	0.9627	0.127*
H3B	0.8898	0.3264	1.0579	0.127*
C4	0.5863 (6)	0.2288 (4)	1.0287 (2)	0.0850 (10)
H4A	0.6135	0.1614	1.0776	0.102*
H4B	0.4981	0.2969	1.0668	0.102*
C5	0.4558 (5)	0.1713 (3)	0.9314 (3)	0.0797 (9)
H5A	0.3094	0.1388	0.9542	0.096*
H5B	0.5380	0.0976	0.8977	0.096*
C6	0.4189 (5)	0.2718 (3)	0.8486 (2)	0.0746 (8)
H6A	0.3421	0.2296	0.7851	0.090*
H6B	0.3222	0.3407	0.8796	0.090*
C7	0.7428 (4)	0.4599 (2)	0.66113 (17)	0.0436 (5)
C8	0.4457 (4)	0.7360 (2)	0.59286 (18)	0.0433 (5)
C9	0.5690 (4)	0.7871 (2)	0.4999 (2)	0.0575 (6)
H9A	0.5857	0.7177	0.4437	0.086*
H9B	0.7165	0.8197	0.5238	0.086*
H9C	0.4842	0.8567	0.4725	0.086*
C10	0.2493 (4)	0.8097 (2)	0.64002 (17)	0.0438 (5)
C11	0.1000 (4)	0.7543 (2)	0.70977 (19)	0.0516 (6)
H11	0.1192	0.6689	0.7279	0.062*
C12	−0.0774 (4)	0.8277 (3)	0.7519 (2)	0.0627 (7)
H12	−0.1794	0.7929	0.7993	0.075*
C13	−0.1011 (5)	0.9530 (3)	0.7227 (2)	0.0702 (8)
H13	−0.2191	1.0048	0.7500	0.084*
C14	0.0518 (5)	1.0001 (3)	0.6527 (3)	0.0768 (9)
H14	0.0339	1.0850	0.6327	0.092*
H1	0.478 (3)	0.474 (2)	0.743 (2)	0.065 (8)*
H2	0.768 (4)	0.579 (3)	0.5503 (14)	0.065 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0544 (4)	0.0507 (4)	0.0685 (4)	0.0198 (3)	0.0197 (3)	0.0228 (3)
N1	0.0532 (11)	0.0492 (12)	0.0560 (11)	0.0178 (9)	0.0174 (9)	0.0209 (9)
N2	0.0480 (10)	0.0408 (11)	0.0557 (11)	0.0121 (8)	0.0150 (9)	0.0165 (9)
N3	0.0448 (9)	0.0368 (10)	0.0527 (11)	0.0086 (7)	0.0091 (8)	0.0101 (8)
N4	0.0693 (13)	0.0387 (12)	0.0918 (16)	0.0159 (10)	0.0248 (12)	0.0197 (11)
C1	0.0587 (13)	0.0454 (13)	0.0517 (13)	0.0179 (10)	0.0168 (11)	0.0172 (11)
C2	0.0801 (19)	0.084 (2)	0.0717 (18)	−0.0111 (16)	0.0005 (15)	0.0302 (16)
C3	0.101 (3)	0.137 (3)	0.087 (2)	−0.018 (2)	−0.0175 (19)	0.062 (2)
C4	0.103 (2)	0.090 (2)	0.0679 (19)	0.0107 (19)	0.0187 (17)	0.0400 (17)
C5	0.088 (2)	0.067 (2)	0.089 (2)	−0.0019 (16)	0.0221 (17)	0.0356 (17)
C6	0.0723 (18)	0.078 (2)	0.0778 (19)	−0.0094 (15)	0.0030 (15)	0.0351 (16)
C7	0.0480 (12)	0.0358 (12)	0.0479 (12)	0.0066 (9)	0.0061 (10)	0.0085 (9)
C8	0.0479 (12)	0.0338 (11)	0.0495 (12)	0.0041 (9)	0.0055 (9)	0.0101 (9)
C9	0.0650 (15)	0.0477 (14)	0.0633 (15)	0.0124 (11)	0.0193 (12)	0.0206 (12)
C10	0.0480 (11)	0.0365 (12)	0.0479 (12)	0.0061 (9)	0.0031 (10)	0.0080 (10)
C11	0.0543 (13)	0.0455 (14)	0.0568 (14)	0.0105 (10)	0.0090 (11)	0.0120 (11)
C12	0.0603 (15)	0.0694 (19)	0.0594 (15)	0.0102 (13)	0.0161 (12)	0.0079 (13)
C13	0.0689 (17)	0.0608 (18)	0.0806 (19)	0.0243 (14)	0.0174 (15)	−0.0027 (15)
C14	0.0823 (19)	0.0418 (15)	0.109 (2)	0.0219 (13)	0.0256 (18)	0.0138 (15)

Geometric parameters (Å, º) top

S1—C7	1.678 (2)	C4—H4A	0.9700
N1—C7	1.332 (3)	C4—H4B	0.9700
N1—C1	1.457 (3)	C5—C6	1.529 (4)
N1—H1	0.870 (10)	C5—H5A	0.9700
N2—C7	1.359 (3)	C5—H5B	0.9700
N2—N3	1.374 (2)	C6—H6A	0.9700
N2—H2	0.878 (10)	C6—H6B	0.9700
N3—C8	1.281 (3)	C8—C10	1.488 (3)
N4—C10	1.331 (3)	C8—C9	1.491 (3)
N4—C14	1.336 (3)	C9—H9A	0.9600
C1—C2	1.503 (4)	C9—H9B	0.9600
C1—C6	1.512 (3)	C9—H9C	0.9600
C1—H1A	0.9800	C10—C11	1.384 (3)
C2—C3	1.523 (4)	C11—C12	1.377 (3)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C13	1.370 (4)
C3—C4	1.508 (5)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.364 (4)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.498 (5)	C14—H14	0.9300

C7—N1—C1	125.56 (19)	C6—C5—H5B	109.2
C7—N1—H1	114.1 (18)	H5A—C5—H5B	107.9
C1—N1—H1	120.3 (18)	C1—C6—C5	111.2 (2)
C7—N2—N3	118.18 (18)	C1—C6—H6A	109.4
C7—N2—H2	115.9 (18)	C5—C6—H6A	109.4
N3—N2—H2	125.6 (18)	C1—C6—H6B	109.4
C8—N3—N2	119.02 (18)	C5—C6—H6B	109.4
C10—N4—C14	117.7 (2)	H6A—C6—H6B	108.0
N1—C1—C2	111.2 (2)	N1—C7—N2	115.73 (19)
N1—C1—C6	110.3 (2)	N1—C7—S1	124.18 (17)
C2—C1—C6	110.8 (2)	N2—C7—S1	120.08 (16)
N1—C1—H1A	108.1	N3—C8—C10	114.81 (19)
C2—C1—H1A	108.1	N3—C8—C9	126.0 (2)
C6—C1—H1A	108.1	C10—C8—C9	119.19 (19)
C1—C2—C3	111.7 (3)	C8—C9—H9A	109.5
C1—C2—H2A	109.3	C8—C9—H9B	109.5
C3—C2—H2A	109.3	H9A—C9—H9B	109.5
C1—C2—H2B	109.3	C8—C9—H9C	109.5
C3—C2—H2B	109.3	H9A—C9—H9C	109.5
H2A—C2—H2B	107.9	H9B—C9—H9C	109.5
C4—C3—C2	111.2 (3)	N4—C10—C11	122.2 (2)
C4—C3—H3A	109.4	N4—C10—C8	116.23 (19)
C2—C3—H3A	109.4	C11—C10—C8	121.5 (2)
C4—C3—H3B	109.4	C12—C11—C10	119.0 (2)
C2—C3—H3B	109.4	C12—C11—H11	120.5
H3A—C3—H3B	108.0	C10—C11—H11	120.5
C5—C4—C3	110.2 (3)	C13—C12—C11	118.8 (2)
C5—C4—H4A	109.6	C13—C12—H12	120.6
C3—C4—H4A	109.6	C11—C12—H12	120.6
C5—C4—H4B	109.6	C12—C13—C14	118.7 (3)
C3—C4—H4B	109.6	C12—C13—H13	120.7
H4A—C4—H4B	108.1	C14—C13—H13	120.7
C4—C5—C6	111.9 (3)	N4—C14—C13	123.6 (3)
C4—C5—H5A	109.2	N4—C14—H14	118.2
C6—C5—H5A	109.2	C13—C14—H14	118.2
C4—C5—H5B	109.2

C7—N2—N3—C8	173.2 (2)	N2—N3—C8—C10	−178.40 (18)
C7—N1—C1—C2	87.7 (3)	N2—N3—C8—C9	0.0 (3)
C7—N1—C1—C6	−149.0 (2)	C14—N4—C10—C11	0.3 (4)
N1—C1—C2—C3	178.0 (3)	C14—N4—C10—C8	−179.7 (2)
C6—C1—C2—C3	54.9 (3)	N3—C8—C10—N4	164.7 (2)
C1—C2—C3—C4	−56.3 (4)	C9—C8—C10—N4	−13.9 (3)
C2—C3—C4—C5	56.3 (4)	N3—C8—C10—C11	−15.3 (3)
C3—C4—C5—C6	−56.3 (4)	C9—C8—C10—C11	166.1 (2)
N1—C1—C6—C5	−177.8 (2)	N4—C10—C11—C12	−0.7 (4)
C2—C1—C6—C5	−54.2 (3)	C8—C10—C11—C12	179.3 (2)
C4—C5—C6—C1	55.7 (4)	C10—C11—C12—C13	0.4 (4)
C1—N1—C7—N2	−176.6 (2)	C11—C12—C13—C14	0.2 (4)
C1—N1—C7—S1	4.3 (3)	C10—N4—C14—C13	0.3 (5)
N3—N2—C7—N1	8.8 (3)	C12—C13—C14—N4	−0.6 (5)
N3—N2—C7—S1	−172.17 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyridyl ring [ok as edited?]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.87 (2)	2.16 (2)	2.592 (3)	111 (2)
C9—H9C···N4	0.96	2.39	2.822 (3)	107
N2—H2···S1ⁱ	0.88 (2)	2.73 (2)	3.610 (2)	174 (2)
C9—H9B···Cg1ⁱⁱ	0.96	2.89	3.776 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₄S
M_r	276.40
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.8824 (6), 10.2410 (9), 12.3902 (14)
α, β, γ (°)	94.718 (8), 90.427 (9), 90.979 (8)
V (Å³)	743.74 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent Supernova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent Technologies, 2010)
T_min, T_max	0.842, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5817, 3292, 2355
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.151, 1.04
No. of reflections	3292
No. of parameters	181
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: CrysAlis PRO (Agilent Technologies, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyridyl ring [ok as edited?]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.867 (19)	2.16 (2)	2.592 (3)	110.8 (17)
C9—H9C···N4	0.96	2.39	2.822 (3)	107
N2—H2···S1ⁱ	0.88 (2)	2.73 (2)	3.610 (2)	174 (2)
C9—H9B···Cg1ⁱⁱ	0.96	2.89	3.776 (3)	155

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

Footnotes

‡Additional correspondence author, e-mail: maaffan@frst.unimas.my.

Acknowledgements

This work was supported financially by the Ministry of Science, Technology and Innovation (MOSTI) under research grant No. 06-01-09-SF0046. The authors thank Universiti Malaysia Sarawak (UNIMAS) for the facilities to carry out the research work. The authors also thank the University of Malaya for support of the crystallographic facility.

References

Agilent Technologies (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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