(Z)-2-(5-Methyl-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide

Qasem Ali, A.; Eltayeb, N.E.; Teoh, S.G.; Salhin, A.; Fun, H.-K.

doi:10.1107/S1600536811049154

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3476-o3477

https://doi.org/10.1107/S1600536811049154

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(Z)-2-(5-Methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide

Amna Qasem Ali,^a,^b Naser Eltaher Eltayeb,^a,^c ‡ Siang Guan Teoh,^a ^* Abdussalam Salhin ^a and Hoong-Kun Fun ^d §

^aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, ^bFaculty of Science, Sabha University, Libya, ^cDepartment of Chemistry, International University of Africa, Khartoum, Sudan, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 29 October 2011; accepted 18 November 2011; online 30 November 2011)

In the title compound, C₁₆H₁₄N₄OS, the dihedral angle between the nine-membered 5-methylindolin-2-one ring system and the benzene ring is 10.21 (7)°. Intramolecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding interactions [graph set S(6)] are present within the N—N—C—N chain between the ring systems. In the crystal, molecules form centrosymmetric cyclic dimers through pairs of N—H⋯O hydrogen bonds [graph set R₂²(8)].

Related literature

For related structures, see: Qasem Ali et al. (2011 ); Ferrari et al. (2002 ); Pervez et al. (2010 ); Ramzan et al. (2010 ). For the biological activity of Schiff bases, see: Bhandari et al. (2008 ); Bhardwaj et al. (2010 ); Pandeya et al. (1999 ); Sridhar et al. (2002 ); Suryavanshi & Pai (2006 ). For the cytotoxic and anticancer activiy of isatin and its derivatives, see: Vine et al. (2009 ). For bond-length data, see; Allen et al. (1987 ). For graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₄N₄OS
M_r = 310.37
Monoclinic, P 2₁ /c
a = 5.6875 (3) Å
b = 17.9405 (8) Å
c = 14.5658 (6) Å
β = 91.105 (3)°
V = 1485.97 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.37 × 0.14 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.921, T_max = 0.980
25266 measured reflections
4645 independent reflections
3565 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.123
S = 1.06
4645 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.89 (2)	1.96 (2)	2.848 (2)	173 (2)
N3—H1N3⋯O1	0.91 (2)	2.04 (2)	2.7595 (17)	135.8 (19)
C11—H11A⋯S1	0.95	2.63	3.2712 (18)	125
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049154/zs2160sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049154/zs2160Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049154/zs2160Isup3.cml

checkCIF report

Comment top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. Biological properties of isatin and its derivatives include a range of actions in the brain and offer protection against certain types of infections, such as antibacterial (Suryavanshi & Pai, 2006) antifungal, anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-2-(5-chloro-2- oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011). In the present paper we describe the single-crystal X-ray diffraction study of title compound, C₁₆H₁₄N₄OS.

In this compound (Fig. 1), the dihedral angle between the nine-membered 5-methylindolin-2-one ring system and the benzene ring is 10.21 (7)°. The atoms C8 in the 5-methylindolin-2-one ring and C10 in the benzene ring are connected by a chain of four atoms (N2/N3/C9/N4)) giving a torsion angle of 7.3 (2)°, while the torsion angles (C8/N2/N3/C9) and (C10/N4/C9/N3) are 173.20 (15)° and -177.56 (16)°, respectively. These values are very close to those in the previously mentioned analogous structure (Qasem Ali et al., 2011). The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H···O1 and C11—H···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1) together with an S(5) N4—H···N2 interaction.

In the crystal the molecules form centrosymmetric cyclic dimers through intermolecular N1—H···O1ⁱ hydrogen bonds [graph set R²₂(8)] (Table 1) (Fig. 2). Weak C—H···π interactions are also present: C5—H5A···Cg3ⁱⁱ = 3.6506 (19) Å; C12—H12A···Cg2ⁱⁱⁱ = 3.6600 (19) Å. [Cg3ⁱⁱ is the centroid of the C10—C15 ring; Cg2ⁱⁱⁱ is the centroid of the C1—C6 ring: symmetry code: (ii) = -x + 1, y + 1/2, -z + 1/2; (iii) = -x, y - 1/2, -z + 1/2].

Related literature top

For related structures, see: Qasem Ali et al. (2011); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For the biological activity of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activiy of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The title compound was synthesized by refluxing the reaction mixture of 4-phenyl-3-thiosemicarbazide (0.01 mol) and 5-methylisatin (0.01 mol) in 60 ml of ethanol for 2 hrs. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH: yield 80%. The orange crystals (m.p. 511.8–512.3 K) were grown in acetone-DMF (3:1) by slow evaporation at room temperature.

Structure description top

For related structures, see: Qasem Ali et al. (2011); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For the biological activity of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activiy of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).

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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular conformation of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed down the a axis of the unit cell. Hydrogen bonds are shown as dashed lines.

(Z)-2-(5-Methyl-2-oxoindolin-3-ylidene)-N- phenylhydrazinecarbothioamide top

Crystal data top

C₁₆H₁₄N₄OS	F(000) = 648
M_r = 310.37	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 511.8–512.3 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.6875 (3) Å	Cell parameters from 4470 reflections
b = 17.9405 (8) Å	θ = 3.0–30.2°
c = 14.5658 (6) Å	µ = 0.23 mm⁻¹
β = 91.105 (3)°	T = 100 K
V = 1485.97 (12) Å³	Block, orange
Z = 4	0.37 × 0.14 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	4645 independent reflections
Radiation source: fine-focus sealed tube	3565 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ and ω scans	θ_max = 30.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.921, T_max = 0.980	k = −25→22
25266 measured reflections	l = −20→20

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.044P)² + 0.9076P] where P = (F_o² + 2F_c²)/3
4645 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₄N₄OS	V = 1485.97 (12) Å³
M_r = 310.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6875 (3) Å	µ = 0.23 mm⁻¹
b = 17.9405 (8) Å	T = 100 K
c = 14.5658 (6) Å	0.37 × 0.14 × 0.09 mm
β = 91.105 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4645 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3565 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.980	R_int = 0.080
25266 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.40 e Å⁻³
4645 reflections	Δρ_min = −0.30 e Å⁻³
212 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	0.07706 (8)	0.29276 (3)	0.01263 (3)	0.02056 (12)
O1	0.7096 (2)	0.44974 (7)	0.01110 (8)	0.0187 (3)
N1	0.9164 (3)	0.52631 (8)	0.11276 (10)	0.0179 (3)
N2	0.3961 (2)	0.43175 (8)	0.17539 (10)	0.0150 (3)
N3	0.3233 (2)	0.39394 (8)	0.09997 (10)	0.0162 (3)
N4	0.0280 (2)	0.34699 (8)	0.18614 (10)	0.0159 (3)
C1	0.6987 (3)	0.51350 (9)	0.24304 (12)	0.0165 (3)
C2	0.6453 (3)	0.52430 (10)	0.33500 (12)	0.0184 (3)
H2A	0.5077	0.5027	0.3598	0.022*
C3	0.7961 (3)	0.56718 (10)	0.39045 (12)	0.0193 (3)
C4	0.9965 (3)	0.59863 (10)	0.35161 (13)	0.0206 (4)
H4A	1.0989	0.6276	0.3895	0.025*
C5	1.0518 (3)	0.58900 (10)	0.25912 (13)	0.0208 (4)
H5A	1.1879	0.6110	0.2338	0.025*
C6	0.8998 (3)	0.54610 (10)	0.20639 (12)	0.0169 (3)
C7	0.7392 (3)	0.47997 (9)	0.08672 (12)	0.0161 (3)
C8	0.5860 (3)	0.47119 (9)	0.16929 (11)	0.0155 (3)
C9	0.1363 (3)	0.34475 (9)	0.10484 (11)	0.0149 (3)
C10	−0.1620 (3)	0.30520 (9)	0.22098 (11)	0.0153 (3)
C11	−0.3260 (3)	0.26716 (9)	0.16670 (12)	0.0173 (3)
H11A	−0.3118	0.2663	0.1018	0.021*
C12	−0.5113 (3)	0.23029 (10)	0.20818 (13)	0.0200 (3)
H12A	−0.6224	0.2039	0.1711	0.024*
C13	−0.5366 (3)	0.23132 (10)	0.30262 (13)	0.0230 (4)
H13A	−0.6641	0.2060	0.3301	0.028*
C14	−0.3733 (3)	0.26977 (12)	0.35662 (13)	0.0250 (4)
H14A	−0.3896	0.2711	0.4214	0.030*
C15	−0.1861 (3)	0.30627 (11)	0.31617 (12)	0.0218 (4)
H15A	−0.0740	0.3321	0.3535	0.026*
C16	0.7427 (4)	0.58122 (12)	0.48997 (13)	0.0275 (4)
H16A	0.5743	0.5738	0.4998	0.041*
H16B	0.7858	0.6325	0.5061	0.041*
H16C	0.8332	0.5465	0.5287	0.041*
H1N4	0.095 (4)	0.3741 (12)	0.2252 (15)	0.021 (5)*
H1N1	1.034 (4)	0.5376 (13)	0.0759 (16)	0.033 (6)*
H1N3	0.410 (4)	0.3965 (12)	0.0486 (15)	0.026 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0242 (2)	0.0211 (2)	0.0166 (2)	−0.00282 (16)	0.00367 (15)	−0.00340 (17)
O1	0.0170 (6)	0.0209 (6)	0.0183 (6)	0.0005 (5)	0.0041 (4)	0.0018 (5)
N1	0.0150 (6)	0.0184 (7)	0.0205 (7)	−0.0013 (5)	0.0072 (5)	0.0019 (6)
N2	0.0152 (6)	0.0132 (7)	0.0166 (7)	0.0008 (5)	0.0025 (5)	0.0017 (5)
N3	0.0167 (6)	0.0164 (7)	0.0156 (7)	−0.0017 (5)	0.0048 (5)	−0.0001 (5)
N4	0.0166 (6)	0.0164 (7)	0.0146 (7)	−0.0041 (5)	0.0029 (5)	−0.0003 (6)
C1	0.0147 (7)	0.0148 (8)	0.0199 (8)	−0.0004 (6)	0.0020 (6)	0.0027 (6)
C2	0.0191 (8)	0.0172 (8)	0.0191 (8)	−0.0015 (6)	0.0044 (6)	0.0026 (7)
C3	0.0223 (8)	0.0152 (8)	0.0206 (8)	−0.0003 (6)	0.0015 (6)	0.0008 (7)
C4	0.0206 (8)	0.0162 (8)	0.0250 (9)	−0.0029 (6)	−0.0011 (7)	0.0012 (7)
C5	0.0161 (7)	0.0178 (9)	0.0287 (9)	−0.0025 (6)	0.0042 (6)	0.0014 (7)
C6	0.0148 (7)	0.0148 (8)	0.0212 (8)	0.0015 (6)	0.0040 (6)	0.0026 (6)
C7	0.0148 (7)	0.0135 (8)	0.0204 (8)	0.0028 (5)	0.0041 (6)	0.0055 (6)
C8	0.0136 (7)	0.0156 (8)	0.0174 (8)	0.0007 (6)	0.0038 (6)	0.0038 (6)
C9	0.0154 (7)	0.0137 (8)	0.0157 (8)	0.0001 (6)	0.0014 (6)	0.0025 (6)
C10	0.0137 (7)	0.0137 (8)	0.0186 (8)	−0.0008 (5)	0.0031 (6)	0.0028 (6)
C11	0.0172 (7)	0.0160 (8)	0.0187 (8)	0.0011 (6)	0.0007 (6)	0.0001 (6)
C12	0.0158 (7)	0.0162 (8)	0.0279 (9)	−0.0010 (6)	0.0002 (6)	−0.0001 (7)
C13	0.0166 (8)	0.0206 (9)	0.0319 (10)	−0.0006 (6)	0.0053 (7)	0.0069 (7)
C14	0.0205 (8)	0.0364 (11)	0.0184 (8)	−0.0023 (7)	0.0046 (7)	0.0057 (8)
C15	0.0182 (8)	0.0296 (10)	0.0175 (8)	−0.0038 (7)	0.0011 (6)	0.0013 (7)
C16	0.0351 (10)	0.0269 (10)	0.0205 (9)	−0.0088 (8)	0.0030 (7)	−0.0025 (8)

Geometric parameters (Å, º) top

S1—C9	1.6643 (17)	C4—C5	1.400 (3)
O1—C7	1.236 (2)	C4—H4A	0.9500
N1—C7	1.355 (2)	C5—C6	1.380 (2)
N1—C6	1.414 (2)	C5—H5A	0.9500
N1—H1N1	0.89 (3)	C7—C8	1.507 (2)
N2—C8	1.296 (2)	C10—C11	1.390 (2)
N2—N3	1.349 (2)	C10—C15	1.396 (2)
N3—C9	1.385 (2)	C11—C12	1.392 (2)
N3—H1N3	0.91 (2)	C11—H11A	0.9500
N4—C9	1.346 (2)	C12—C13	1.386 (3)
N4—C10	1.417 (2)	C12—H12A	0.9500
N4—H1N4	0.84 (2)	C13—C14	1.389 (3)
C1—C2	1.393 (2)	C13—H13A	0.9500
C1—C6	1.400 (2)	C14—C15	1.391 (2)
C1—C8	1.454 (2)	C14—H14A	0.9500
C2—C3	1.397 (2)	C15—H15A	0.9500
C2—H2A	0.9500	C16—H16A	0.9800
C3—C4	1.401 (2)	C16—H16B	0.9800
C3—C16	1.508 (3)	C16—H16C	0.9800

C7—N1—C6	111.17 (14)	N2—C8—C1	126.19 (15)
C7—N1—H1N1	122.3 (15)	N2—C8—C7	127.40 (16)
C6—N1—H1N1	126.2 (15)	C1—C8—C7	106.37 (13)
C8—N2—N3	117.49 (14)	N4—C9—N3	113.02 (15)
N2—N3—C9	120.16 (14)	N4—C9—S1	129.63 (13)
N2—N3—H1N3	119.0 (14)	N3—C9—S1	117.35 (12)
C9—N3—H1N3	120.3 (14)	C11—C10—C15	119.59 (15)
C9—N4—C10	131.63 (15)	C11—C10—N4	124.33 (15)
C9—N4—H1N4	113.8 (15)	C15—C10—N4	116.02 (15)
C10—N4—H1N4	114.0 (15)	C10—C11—C12	119.45 (16)
C2—C1—C6	120.24 (16)	C10—C11—H11A	120.3
C2—C1—C8	133.01 (15)	C12—C11—H11A	120.3
C6—C1—C8	106.74 (15)	C13—C12—C11	121.24 (17)
C1—C2—C3	119.32 (16)	C13—C12—H12A	119.4
C1—C2—H2A	120.3	C11—C12—H12A	119.4
C3—C2—H2A	120.3	C12—C13—C14	119.17 (17)
C2—C3—C4	118.91 (17)	C12—C13—H13A	120.4
C2—C3—C16	120.98 (16)	C14—C13—H13A	120.4
C4—C3—C16	120.09 (16)	C13—C14—C15	120.20 (17)
C5—C4—C3	122.58 (17)	C13—C14—H14A	119.9
C5—C4—H4A	118.7	C15—C14—H14A	119.9
C3—C4—H4A	118.7	C14—C15—C10	120.33 (17)
C6—C5—C4	117.04 (16)	C14—C15—H15A	119.8
C6—C5—H5A	121.5	C10—C15—H15A	119.8
C4—C5—H5A	121.5	C3—C16—H16A	109.5
C5—C6—C1	121.91 (16)	C3—C16—H16B	109.5
C5—C6—N1	128.63 (15)	H16A—C16—H16B	109.5
C1—C6—N1	109.45 (15)	C3—C16—H16C	109.5
O1—C7—N1	127.33 (15)	H16A—C16—H16C	109.5
O1—C7—C8	126.46 (15)	H16B—C16—H16C	109.5
N1—C7—C8	106.20 (15)

C8—N2—N3—C9	173.20 (15)	C6—C1—C8—N2	178.90 (16)
C6—C1—C2—C3	−0.8 (3)	C2—C1—C8—C7	−177.55 (18)
C8—C1—C2—C3	177.80 (17)	C6—C1—C8—C7	1.20 (18)
C1—C2—C3—C4	0.5 (3)	O1—C7—C8—N2	−1.1 (3)
C1—C2—C3—C16	179.03 (17)	N1—C7—C8—N2	179.90 (16)
C2—C3—C4—C5	0.2 (3)	O1—C7—C8—C1	176.55 (16)
C16—C3—C4—C5	−178.40 (18)	N1—C7—C8—C1	−2.43 (18)
C3—C4—C5—C6	−0.5 (3)	C10—N4—C9—N3	−177.56 (16)
C4—C5—C6—C1	0.1 (3)	C10—N4—C9—S1	2.6 (3)
C4—C5—C6—N1	−178.48 (17)	N2—N3—C9—N4	7.3 (2)
C2—C1—C6—C5	0.5 (3)	N2—N3—C9—S1	−172.89 (12)
C8—C1—C6—C5	−178.41 (16)	C9—N4—C10—C11	−21.0 (3)
C2—C1—C6—N1	179.35 (15)	C9—N4—C10—C15	161.84 (18)
C8—C1—C6—N1	0.42 (19)	C15—C10—C11—C12	−0.4 (3)
C7—N1—C6—C5	176.62 (17)	N4—C10—C11—C12	−177.43 (16)
C7—N1—C6—C1	−2.1 (2)	C10—C11—C12—C13	0.6 (3)
C6—N1—C7—O1	−176.20 (16)	C11—C12—C13—C14	−0.2 (3)
C6—N1—C7—C8	2.77 (18)	C12—C13—C14—C15	−0.4 (3)
N3—N2—C8—C1	−177.47 (15)	C13—C14—C15—C10	0.6 (3)
N3—N2—C8—C7	−0.2 (2)	C11—C10—C15—C14	−0.2 (3)
C2—C1—C8—N2	0.2 (3)	N4—C10—C15—C14	177.06 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N2	0.84 (2)	2.14 (2)	2.5947 (18)	114.1 (18)
N1—H1N1···O1ⁱ	0.89 (2)	1.96 (2)	2.848 (2)	173 (2)
N3—H1N3···O1	0.91 (2)	2.04 (2)	2.7595 (17)	135.8 (19)
C11—H11A···S1	0.95	2.63	3.2712 (18)	125

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄OS
M_r	310.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.6875 (3), 17.9405 (8), 14.5658 (6)
β (°)	91.105 (3)
V (Å³)	1485.97 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.37 × 0.14 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.921, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	25266, 4645, 3565
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.722

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.123, 1.06
No. of reflections	4645
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.89 (2)	1.96 (2)	2.848 (2)	173 (2)
N3—H1N3···O1	0.91 (2)	2.04 (2)	2.7595 (17)	135.8 (19)
C11—H11A···S1	0.95	2.63	3.2712 (18)	125

Symmetry code: (i) −x+2, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: E-9395-2011.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing research leave. AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

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