organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o962-o963

(Z)-2-(2-Oxoindolin-3-yl­­idene)-N-phenylhydrazinecarbo­thio­amide

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

(Received 11 January 2012; accepted 30 January 2012; online 7 March 2012)

In the title compound, C15H12N4OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. Intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present, as are weak N—H⋯N inter­actions [graph set S(5)]. In the crystal, mol­ecules form centrosymmetric cyclic dimers through pairs of N—H⋯O hydrogen bonds [graph set R22(8)] and these are extended by C—H⋯S inter­actions. The crystal structure also features weak C—H⋯π inter­actions.

Related literature

For related crystal structures, see: Ali et al. (2012[Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o285-o286.]); Qasem Ali et al. (2011a[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011a). Acta Cryst. E67, o3141-o3142.],b[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011b). Acta Cryst. E67, o3476-o3477.]); Ferrari et al. (2002[Ferrari, M. B., Pelizzi, C., Pelosi, G. & Rodriguez-Argüelles, M. C. (2002). Polyhedron, 21, 2593-2599.]); Pervez et al. (2010[Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010). Acta Cryst. E66, o1609.]); Ramzan et al. (2010[Ramzan, M., Pervez, H., Yaqub, M. & Tahir, M. N. (2010). Acta Cryst. E66, o2387.]). For various biological activities of Schiff bases, see: Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]); Bhardwaj et al. (2010[Bhardwaj, S., Kumar, L., Verma, R. & Sing, U. K. (2010). J. Pharm. Res. 3, 2983-2985.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Indian J. Pharm. Sci. 61, 358-361.]); Sridhar et al. (2002[Sridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129-132.]); Suryavanshi & Pai (2006[Suryavanshi, J. P. & Pai, N. R. (2006). Indian J. Chem. Sect. B, 45, 1227-1230.]). For the cytotoxic and anti­cancer activities of isatin and its derivatives, see: Vine et al. (2009[Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anticancer Agents Med. Chem. 9, 397-414.]). For graph-set analysis, see Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N4OS

  • Mr = 296.35

  • Monoclinic, P 21/c

  • a = 6.3674 (1) Å

  • b = 15.4594 (3) Å

  • c = 14.2199 (3) Å

  • β = 93.383 (1)°

  • V = 1397.31 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 100 K

  • 0.47 × 0.13 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.897, Tmax = 0.971

  • 15557 measured reflections

  • 4159 independent reflections

  • 2985 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.113

  • S = 1.02

  • 4159 reflections

  • 202 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O1i 0.88 (2) 2.00 (2) 2.8737 (18) 173.9 (18)
N3—H1N3⋯O1 0.87 (2) 2.07 (2) 2.7646 (18) 136 (2)
N4—H1N4⋯N2 0.88 (2) 2.05 (2) 2.5781 (19) 117.4 (17)
C11—H11A⋯S1ii 0.95 2.83 3.6017 (19) 139
C15—H15A⋯S1 0.95 2.60 3.2735 (19) 128
C2—H2ACg3iii 0.95 2.80 3.510 (2) 132
C13—H13ACg2iv 0.95 2.82 3.5201 (19) 131
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. The biological properties of isatin and its derivatives include a range of actions in the brain, offer protection against bacterial (Suryavanshi & Pai, 2006) and fungal infections and possess anticonvulsant, anti-HIV (Pandeya et al., 1999), antidepressant 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., 2011a). In the present paper we describe the single-crystal X-ray diffraction study of the title compound (Fig. 1).

In the title compound, C15H12N4OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. These two ring systems are connected by a chain of four atoms N2—N3—C9—N4; this torsion angle is 4.1 (2)°. The torsion angles C7—N2—N3—C9 and C10—N4—C9—N3 are 173.69 (15)° and 174.00 (16)°, respectively. These values are very close to those in a similar structure (Qasem Ali et al., 2011a).

The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H1N3···O1 and C15—H15A···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1), together with a weak S(5) N4—H1N4···N2 interaction.

In the crystal structure, the molecules form centrosymmetric cyclic dimers through intermolecular N1—H1N1···O1 hydrogen bonds [graph set R22(8)] and are extended by C11—H11A···S1 hydrogen bond interactions.

The crystal structure (Fig. 2) is stabilized by weak C—H···π interactions (Table 1) involving the C10–C15 ring (centroid Cg3) and C1–C6 ring (centroid Cg2).

Related literature top

For related crystal structures, see: Ali et al. (2012); Qasem Ali et al. (2011a,b); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For various biological activities 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 activities of isatin and its derivatives, see: Vine et al. (2009). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The Schiff base has been synthesized by refluxing the reaction mixture of a hot ethanolic solution (30 ml) of 4-phenyl-3-thiosemicarbazide (0.01 mol) and a hot ethanolic solution (30 ml) of isatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH. Yield (m.p.): 90% (510.2–511.6 K). The yellow crystals were grown in acetone–dimethylformamide (3:1) by slow evaporation at room temperature.

Refinement top

N-bound H atoms were located in a difference Fourier map and were refined freely; N—H = 0.87 (2) Å and 0.88 (2) Å. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. The biological properties of isatin and its derivatives include a range of actions in the brain, offer protection against bacterial (Suryavanshi & Pai, 2006) and fungal infections and possess anticonvulsant, anti-HIV (Pandeya et al., 1999), antidepressant 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., 2011a). In the present paper we describe the single-crystal X-ray diffraction study of the title compound (Fig. 1).

In the title compound, C15H12N4OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. These two ring systems are connected by a chain of four atoms N2—N3—C9—N4; this torsion angle is 4.1 (2)°. The torsion angles C7—N2—N3—C9 and C10—N4—C9—N3 are 173.69 (15)° and 174.00 (16)°, respectively. These values are very close to those in a similar structure (Qasem Ali et al., 2011a).

The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H1N3···O1 and C15—H15A···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1), together with a weak S(5) N4—H1N4···N2 interaction.

In the crystal structure, the molecules form centrosymmetric cyclic dimers through intermolecular N1—H1N1···O1 hydrogen bonds [graph set R22(8)] and are extended by C11—H11A···S1 hydrogen bond interactions.

The crystal structure (Fig. 2) is stabilized by weak C—H···π interactions (Table 1) involving the C10–C15 ring (centroid Cg3) and C1–C6 ring (centroid Cg2).

For related crystal structures, see: Ali et al. (2012); Qasem Ali et al. (2011a,b); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For various biological activities 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 activities of isatin and its derivatives, see: Vine et al. (2009). 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
[Figure 1] Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
(Z)-2-(2-Oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide top
Crystal data top
C15H12N4OSF(000) = 616
Mr = 296.35Dx = 1.409 Mg m3
Monoclinic, P21/cMelting point = 510.2–511.6 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.3674 (1) ÅCell parameters from 4743 reflections
b = 15.4594 (3) Åθ = 3.0–30.1°
c = 14.2199 (3) ŵ = 0.24 mm1
β = 93.383 (1)°T = 100 K
V = 1397.31 (5) Å3Needle, yellow
Z = 40.47 × 0.13 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
4159 independent reflections
Radiation source: fine-focus sealed tube2985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 30.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 98
Tmin = 0.897, Tmax = 0.971k = 2118
15557 measured reflectionsl = 1720
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.038P)2 + 0.7736P]
where P = (Fo2 + 2Fc2)/3
4159 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C15H12N4OSV = 1397.31 (5) Å3
Mr = 296.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.3674 (1) ŵ = 0.24 mm1
b = 15.4594 (3) ÅT = 100 K
c = 14.2199 (3) Å0.47 × 0.13 × 0.13 mm
β = 93.383 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
4159 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2985 reflections with I > 2σ(I)
Tmin = 0.897, Tmax = 0.971Rint = 0.040
15557 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.34 e Å3
4159 reflectionsΔρmin = 0.49 e Å3
202 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
xyzUiso*/Ueq
S10.15701 (8)0.72368 (4)1.06040 (3)0.03145 (15)
O10.73491 (19)0.55698 (8)1.00760 (8)0.0228 (3)
N10.9075 (2)0.50533 (10)0.87950 (10)0.0208 (3)
N20.4169 (2)0.61290 (9)0.85318 (10)0.0177 (3)
N30.3689 (2)0.63773 (9)0.94027 (10)0.0191 (3)
N40.0843 (2)0.70518 (9)0.87089 (10)0.0181 (3)
C10.8690 (3)0.50379 (11)0.78102 (12)0.0195 (4)
C20.9950 (3)0.47108 (12)0.71370 (13)0.0241 (4)
H2A1.12640.44450.73060.029*
C30.9210 (3)0.47880 (12)0.61995 (13)0.0253 (4)
H3A1.00270.45600.57190.030*
C40.7296 (3)0.51916 (12)0.59478 (13)0.0231 (4)
H4A0.68460.52430.53010.028*
C50.6042 (3)0.55185 (11)0.66319 (12)0.0206 (4)
H5A0.47410.57940.64620.025*
C60.6740 (3)0.54324 (11)0.75712 (12)0.0184 (4)
C70.5904 (3)0.57114 (11)0.84497 (12)0.0176 (3)
C80.7491 (3)0.54476 (11)0.92218 (12)0.0188 (4)
C90.1964 (3)0.68962 (11)0.95214 (12)0.0185 (4)
C100.1096 (3)0.74787 (11)0.85012 (12)0.0168 (3)
C110.1753 (3)0.74938 (11)0.75467 (12)0.0190 (4)
H11A0.08920.72450.70950.023*
C120.3656 (3)0.78705 (11)0.72568 (13)0.0237 (4)
H12A0.40980.78780.66070.028*
C130.4917 (3)0.82369 (11)0.79112 (13)0.0247 (4)
H13A0.62280.84920.77140.030*
C140.4248 (3)0.82279 (11)0.88559 (13)0.0229 (4)
H14A0.51060.84860.93030.027*
C150.2349 (3)0.78504 (11)0.91642 (12)0.0196 (4)
H15A0.19120.78460.98150.024*
H1N11.018 (3)0.4836 (14)0.9106 (15)0.037 (6)*
H1N30.457 (4)0.6258 (14)0.9879 (16)0.039 (6)*
H1N40.144 (3)0.6806 (14)0.8234 (15)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0267 (2)0.0507 (3)0.0168 (2)0.0076 (2)0.00014 (18)0.0045 (2)
O10.0242 (6)0.0248 (7)0.0189 (6)0.0016 (5)0.0032 (5)0.0026 (5)
N10.0191 (7)0.0199 (8)0.0228 (8)0.0043 (6)0.0032 (6)0.0020 (6)
N20.0189 (7)0.0153 (7)0.0187 (7)0.0008 (6)0.0001 (5)0.0008 (6)
N30.0184 (7)0.0216 (8)0.0171 (7)0.0022 (6)0.0011 (6)0.0020 (6)
N40.0184 (7)0.0193 (8)0.0166 (7)0.0032 (6)0.0014 (6)0.0000 (6)
C10.0195 (8)0.0131 (8)0.0254 (9)0.0000 (7)0.0025 (7)0.0014 (7)
C20.0211 (9)0.0197 (9)0.0315 (10)0.0045 (7)0.0006 (8)0.0030 (8)
C30.0265 (9)0.0231 (9)0.0268 (9)0.0049 (8)0.0064 (8)0.0016 (8)
C40.0248 (9)0.0220 (9)0.0225 (9)0.0017 (7)0.0004 (7)0.0018 (7)
C50.0187 (8)0.0181 (9)0.0248 (9)0.0010 (7)0.0016 (7)0.0016 (7)
C60.0190 (8)0.0140 (8)0.0220 (8)0.0005 (7)0.0007 (7)0.0009 (7)
C70.0183 (8)0.0127 (8)0.0213 (8)0.0015 (6)0.0020 (7)0.0023 (6)
C80.0187 (8)0.0120 (8)0.0254 (9)0.0013 (7)0.0021 (7)0.0031 (7)
C90.0173 (8)0.0186 (8)0.0195 (8)0.0036 (7)0.0016 (6)0.0035 (7)
C100.0164 (8)0.0136 (8)0.0205 (8)0.0016 (6)0.0017 (6)0.0014 (6)
C110.0198 (8)0.0179 (8)0.0194 (8)0.0002 (7)0.0023 (7)0.0013 (7)
C120.0243 (9)0.0204 (9)0.0257 (9)0.0013 (7)0.0043 (7)0.0044 (7)
C130.0187 (8)0.0167 (9)0.0383 (11)0.0006 (7)0.0014 (8)0.0044 (8)
C140.0201 (8)0.0153 (8)0.0339 (10)0.0008 (7)0.0066 (7)0.0026 (8)
C150.0214 (8)0.0165 (8)0.0211 (8)0.0007 (7)0.0024 (7)0.0021 (7)
Geometric parameters (Å, º) top
S1—C91.6600 (18)C4—C51.389 (3)
O1—C81.238 (2)C4—H4A0.9500
N1—C81.352 (2)C5—C61.389 (2)
N1—C11.408 (2)C5—H5A0.9500
N1—H1N10.88 (2)C6—C71.452 (2)
N2—C71.291 (2)C7—C81.504 (2)
N2—N31.349 (2)C10—C151.394 (2)
N3—C91.378 (2)C10—C111.397 (2)
N3—H1N30.87 (2)C11—C121.385 (2)
N4—C91.343 (2)C11—H11A0.9500
N4—C101.416 (2)C12—C131.386 (3)
N4—H1N40.88 (2)C12—H12A0.9500
C1—C21.381 (3)C13—C141.385 (3)
C1—C61.407 (2)C13—H13A0.9500
C2—C31.393 (3)C14—C151.390 (2)
C2—H2A0.9500C14—H14A0.9500
C3—C41.397 (2)C15—H15A0.9500
C3—H3A0.9500
C8—N1—C1111.31 (14)N2—C7—C6125.83 (15)
C8—N1—H1N1123.0 (14)N2—C7—C8127.70 (16)
C1—N1—H1N1125.7 (14)C6—C7—C8106.43 (14)
C7—N2—N3117.83 (14)O1—C8—N1127.51 (15)
N2—N3—C9120.23 (14)O1—C8—C7126.16 (16)
N2—N3—H1N3118.7 (15)N1—C8—C7106.34 (15)
C9—N3—H1N3120.6 (15)N4—C9—N3112.68 (15)
C9—N4—C10132.49 (16)N4—C9—S1129.71 (14)
C9—N4—H1N4110.5 (13)N3—C9—S1117.61 (12)
C10—N4—H1N4116.9 (13)C15—C10—C11119.98 (15)
C2—C1—C6122.14 (16)C15—C10—N4125.29 (15)
C2—C1—N1128.43 (15)C11—C10—N4114.71 (15)
C6—C1—N1109.42 (15)C12—C11—C10120.19 (17)
C1—C2—C3117.03 (16)C12—C11—H11A119.9
C1—C2—H2A121.5C10—C11—H11A119.9
C3—C2—H2A121.5C11—C12—C13120.24 (16)
C2—C3—C4121.63 (18)C11—C12—H12A119.9
C2—C3—H3A119.2C13—C12—H12A119.9
C4—C3—H3A119.2C14—C13—C12119.32 (16)
C5—C4—C3120.78 (16)C14—C13—H13A120.3
C5—C4—H4A119.6C12—C13—H13A120.3
C3—C4—H4A119.6C13—C14—C15121.48 (17)
C6—C5—C4118.29 (16)C13—C14—H14A119.3
C6—C5—H5A120.9C15—C14—H14A119.3
C4—C5—H5A120.9C14—C15—C10118.79 (16)
C5—C6—C1120.11 (17)C14—C15—H15A120.6
C5—C6—C7133.33 (16)C10—C15—H15A120.6
C1—C6—C7106.50 (14)
C7—N2—N3—C9173.69 (15)C1—N1—C8—O1179.73 (17)
C8—N1—C1—C2178.50 (18)C1—N1—C8—C70.46 (18)
C8—N1—C1—C60.7 (2)N2—C7—C8—O12.3 (3)
C6—C1—C2—C30.1 (3)C6—C7—C8—O1179.84 (16)
N1—C1—C2—C3179.09 (17)N2—C7—C8—N1177.88 (17)
C1—C2—C3—C41.1 (3)C6—C7—C8—N10.03 (18)
C2—C3—C4—C51.1 (3)C10—N4—C9—N3174.00 (16)
C3—C4—C5—C60.1 (3)C10—N4—C9—S16.4 (3)
C4—C5—C6—C11.2 (3)N2—N3—C9—N44.1 (2)
C4—C5—C6—C7177.76 (18)N2—N3—C9—S1175.54 (12)
C2—C1—C6—C51.3 (3)C9—N4—C10—C150.6 (3)
N1—C1—C6—C5178.05 (15)C9—N4—C10—C11179.21 (17)
C2—C1—C6—C7178.61 (16)C15—C10—C11—C120.6 (3)
N1—C1—C6—C70.69 (19)N4—C10—C11—C12178.11 (15)
N3—N2—C7—C6176.52 (15)C10—C11—C12—C130.2 (3)
N3—N2—C7—C80.9 (3)C11—C12—C13—C140.5 (3)
C5—C6—C7—N20.6 (3)C12—C13—C14—C150.8 (3)
C1—C6—C7—N2177.50 (16)C13—C14—C15—C100.4 (3)
C5—C6—C7—C8177.26 (19)C11—C10—C15—C140.3 (2)
C1—C6—C7—C80.40 (18)N4—C10—C15—C14178.24 (16)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.88 (2)2.00 (2)2.8737 (18)173.9 (18)
N3—H1N3···O10.87 (2)2.07 (2)2.7646 (18)136 (2)
N4—H1N4···N20.88 (2)2.05 (2)2.5781 (19)117.4 (17)
C11—H11A···S1ii0.952.833.6017 (19)139
C15—H15A···S10.952.603.2735 (19)128
C2—H2A···Cg3iii0.952.803.510 (2)132
C13—H13A···Cg2iv0.952.823.5201 (19)131
Symmetry codes: (i) x+2, y+1, z+2; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+3/2; (iv) x, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC15H12N4OS
Mr296.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)6.3674 (1), 15.4594 (3), 14.2199 (3)
β (°) 93.383 (1)
V3)1397.31 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.47 × 0.13 × 0.13
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.897, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
15557, 4159, 2985
Rint0.040
(sin θ/λ)max1)0.709
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.113, 1.02
No. of reflections4159
No. of parameters202
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.49

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
Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.88 (2)2.00 (2)2.8737 (18)173.9 (18)
N3—H1N3···O10.87 (2)2.07 (2)2.7646 (18)136 (2)
N4—H1N4···N20.88 (2)2.05 (2)2.5781 (19)117.4 (17)
C11—H11A···S1ii0.95002.83003.6017 (19)139.00
C15—H15A···S10.95002.60003.2735 (19)128.00
C2—H2A···Cg3iii0.95002.80003.510 (2)132.00
C13—H13A···Cg2iv0.95002.82003.5201 (19)131.00
Symmetry codes: (i) x+2, y+1, z+2; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+3/2; (iv) x, y+1/2, z+3/2.
 

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 a Research University grant (No. 1001/PKIMIA/815067). AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholar­ship.

References

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Volume 68| Part 4| April 2012| Pages o962-o963
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