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 o955-o956

(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl­­idene)hydrazinecarbo­thio­amide

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 January 2012; accepted 7 February 2012; online 3 March 2012)

In the title compound, C11H12N4OS, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol­ecules form a helical chain along the a axis through an N—H⋯O hydrogen bond. These chains are extended by an N—H⋯S hydrogen bond and a C—H⋯π inter­action into a three-dimensional network.

Related literature

For related 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. (2012[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o953-o954.], 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.]). 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 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
  • C11H12N4OS

  • Mr = 248.31

  • Orthorhombic, P 21 21 21

  • a = 6.2826 (2) Å

  • b = 10.0341 (3) Å

  • c = 19.1315 (5) Å

  • V = 1206.05 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 100 K

  • 0.51 × 0.18 × 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 = 0.879, Tmax = 0.967

  • 13743 measured reflections

  • 3780 independent reflections

  • 3463 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.07

  • 3780 reflections

  • 168 parameters

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

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.24 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1584 Friedel pairs

  • Flack parameter: −0.08 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O1i 0.81 (2) 2.03 (2) 2.8319 (17) 171 (2)
N3—H1N3⋯O1 0.84 (2) 2.079 (19) 2.7525 (17) 136.9 (17)
N4—H1N4⋯S1ii 0.80 (2) 2.85 (2) 3.5538 (13) 148.5 (19)
C3—H3ACg2iii 0.95 2.62 3.4165 (16) 142
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

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. 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), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (Ali et al., 2012). In the present paper we describe the single-crystal X-ray diffraction study of title compound.

In this compound (Fig. 1), the chain N2/N3/C9/S1/N4/C10 connects to the nine-membered 5-methylindolin-2-one ring system at C7. In this chain, C7/N2/N3/C9 and C10/N4/C9/S1 have torsion angles -176.69 (13) and -1.4 (2)°, respectively. The essentially planar conformation of the molecule is maintained by the cyclic intramolecular N3—H1N3···O1 hydrogen-bond (Table 1) [graph set S(6); Bernstein et al., 1995)]. In the crystal, the molecules form a helical chain through an intermolecular N1—H1N1···O1 hydrogen bond and are extended by an N4—H1N4···S1 hydrogen bond and a weak C3—H3A···Cg2 interaction into a three-dimensional network (Table 1, Fig. 2). Cg2 is the centroid of the C1–C6 ring.

Related literature top

For related structures, see: Ali et al. (2012); Qasem Ali et al. (2012, 2011a,b). 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 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 hot ethanolic solution (30 ml) of 5-methyl-3-thiosemicarbazide (0.01 mol) and hot ethanolic solution (30 ml) of 5-methylisatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH (yield 94%, m.p. 551.7–552.2 K). The yellow crystals were grown in acetone–DMF (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. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic ring and C—H = 0.98 Å for methyl group, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C) for aromatic ring and methyl group, respectively. The highest residual electron density peak is located at 0.76 Å from C9 and the deepest hole is located at 0.16 Å from H11C.

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. 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), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (Ali et al., 2012). In the present paper we describe the single-crystal X-ray diffraction study of title compound.

In this compound (Fig. 1), the chain N2/N3/C9/S1/N4/C10 connects to the nine-membered 5-methylindolin-2-one ring system at C7. In this chain, C7/N2/N3/C9 and C10/N4/C9/S1 have torsion angles -176.69 (13) and -1.4 (2)°, respectively. The essentially planar conformation of the molecule is maintained by the cyclic intramolecular N3—H1N3···O1 hydrogen-bond (Table 1) [graph set S(6); Bernstein et al., 1995)]. In the crystal, the molecules form a helical chain through an intermolecular N1—H1N1···O1 hydrogen bond and are extended by an N4—H1N4···S1 hydrogen bond and a weak C3—H3A···Cg2 interaction into a three-dimensional network (Table 1, Fig. 2). Cg2 is the centroid of the C1–C6 ring.

For related structures, see: Ali et al. (2012); Qasem Ali et al. (2012, 2011a,b). 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 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 and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.
(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3- ylidene)hydrazinecarbothioamide top
Crystal data top
C11H12N4OSDx = 1.368 Mg m3
Mr = 248.31Melting point = 551.7–552.2 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5511 reflections
a = 6.2826 (2) Åθ = 2.3–30.7°
b = 10.0341 (3) ŵ = 0.26 mm1
c = 19.1315 (5) ÅT = 100 K
V = 1206.05 (6) Å3Block, orange
Z = 40.51 × 0.18 × 0.13 mm
F(000) = 520
Data collection top
Bruker APEXII CCD
diffractometer
3780 independent reflections
Radiation source: fine-focus sealed tube3463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 31.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 89
Tmin = 0.879, Tmax = 0.967k = 1413
13743 measured reflectionsl = 2627
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2287P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3780 reflectionsΔρmax = 0.32 e Å3
168 parametersΔρmin = 0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1584 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.08 (7)
Crystal data top
C11H12N4OSV = 1206.05 (6) Å3
Mr = 248.31Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.2826 (2) ŵ = 0.26 mm1
b = 10.0341 (3) ÅT = 100 K
c = 19.1315 (5) Å0.51 × 0.18 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
3780 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3463 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.967Rint = 0.050
13743 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097Δρmax = 0.32 e Å3
S = 1.07Δρmin = 0.24 e Å3
3780 reflectionsAbsolute structure: Flack (1983), with 1584 Friedel pairs
168 parametersAbsolute structure parameter: 0.08 (7)
0 restraints
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
S10.25429 (6)0.29169 (3)0.213725 (19)0.02077 (10)
O10.31886 (18)0.26735 (11)0.06564 (6)0.0214 (2)
N10.6103 (2)0.39581 (13)0.03384 (7)0.0191 (3)
N20.2245 (2)0.50945 (11)0.15475 (6)0.0159 (2)
N30.0861 (2)0.40757 (13)0.16284 (7)0.0171 (2)
N40.1126 (2)0.54025 (13)0.23530 (7)0.0181 (2)
C10.6888 (2)0.52394 (15)0.05069 (8)0.0170 (3)
C20.8718 (2)0.58576 (17)0.02731 (8)0.0206 (3)
H2A0.96610.54270.00420.025*
C30.9124 (2)0.71447 (17)0.05206 (8)0.0217 (3)
H3A1.03860.75860.03740.026*
C40.7740 (2)0.78049 (15)0.09758 (7)0.0202 (3)
C50.5903 (2)0.71534 (15)0.12059 (7)0.0175 (3)
H5A0.49450.75850.15160.021*
C60.5498 (2)0.58673 (15)0.09747 (7)0.0157 (3)
C70.3812 (2)0.49169 (14)0.11202 (7)0.0158 (3)
C80.4287 (2)0.37009 (15)0.06883 (8)0.0175 (3)
C90.0900 (2)0.42245 (14)0.20479 (7)0.0163 (3)
C100.2903 (2)0.57322 (17)0.28065 (9)0.0246 (3)
H10A0.30090.67020.28530.037*
H10B0.26750.53330.32680.037*
H10C0.42230.53830.26040.037*
C110.8227 (3)0.92103 (18)0.12193 (9)0.0288 (4)
H11A0.97670.93610.12040.043*
H11B0.77160.93270.16990.043*
H11C0.75110.98510.09120.043*
H1N10.675 (4)0.345 (2)0.0091 (12)0.030 (6)*
H1N30.105 (3)0.337 (2)0.1401 (10)0.022 (5)*
H1N40.027 (4)0.598 (2)0.2289 (11)0.028 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01781 (16)0.01833 (15)0.02616 (18)0.00367 (14)0.00191 (16)0.00281 (13)
O10.0245 (5)0.0189 (5)0.0207 (5)0.0035 (4)0.0012 (4)0.0036 (4)
N10.0210 (6)0.0189 (6)0.0173 (6)0.0018 (5)0.0025 (5)0.0022 (5)
N20.0162 (6)0.0145 (5)0.0171 (5)0.0021 (4)0.0010 (5)0.0021 (4)
N30.0167 (6)0.0147 (5)0.0200 (6)0.0019 (5)0.0022 (5)0.0016 (4)
N40.0145 (5)0.0195 (6)0.0204 (6)0.0004 (5)0.0015 (5)0.0009 (5)
C10.0175 (6)0.0185 (6)0.0149 (6)0.0012 (5)0.0009 (5)0.0020 (5)
C20.0171 (7)0.0255 (7)0.0191 (7)0.0031 (6)0.0023 (5)0.0038 (6)
C30.0162 (6)0.0277 (7)0.0213 (7)0.0036 (6)0.0010 (5)0.0069 (6)
C40.0211 (7)0.0220 (6)0.0174 (6)0.0062 (6)0.0035 (5)0.0031 (5)
C50.0180 (6)0.0185 (6)0.0161 (6)0.0013 (6)0.0002 (5)0.0003 (5)
C60.0148 (6)0.0184 (6)0.0140 (6)0.0005 (5)0.0001 (5)0.0013 (5)
C70.0167 (6)0.0164 (6)0.0143 (6)0.0005 (5)0.0021 (5)0.0008 (5)
C80.0197 (7)0.0175 (6)0.0154 (6)0.0015 (5)0.0018 (5)0.0015 (5)
C90.0151 (6)0.0170 (6)0.0169 (6)0.0004 (5)0.0026 (5)0.0019 (5)
C100.0195 (7)0.0294 (7)0.0251 (7)0.0036 (6)0.0031 (6)0.0041 (6)
C110.0322 (8)0.0273 (8)0.0271 (8)0.0129 (7)0.0012 (7)0.0017 (7)
Geometric parameters (Å, º) top
S1—C91.6781 (15)C2—H2A0.9500
O1—C81.2419 (18)C3—C41.398 (2)
N1—C81.348 (2)C3—H3A0.9500
N1—C11.414 (2)C4—C51.398 (2)
N1—H1N10.81 (2)C4—C111.516 (2)
N2—C71.2920 (19)C5—C61.388 (2)
N2—N31.3510 (17)C5—H5A0.9500
N3—C91.3749 (19)C6—C71.452 (2)
N3—H1N30.84 (2)C7—C81.503 (2)
N4—C91.3259 (19)C10—H10A0.9800
N4—C101.4520 (19)C10—H10B0.9800
N4—H1N40.80 (2)C10—H10C0.9800
C1—C21.381 (2)C11—H11A0.9800
C1—C61.400 (2)C11—H11B0.9800
C2—C31.399 (2)C11—H11C0.9800
C8—N1—C1110.85 (13)C5—C6—C1120.52 (14)
C8—N1—H1N1127.0 (16)C5—C6—C7133.10 (14)
C1—N1—H1N1122.0 (16)C1—C6—C7106.37 (13)
C7—N2—N3117.30 (12)N2—C7—C6125.90 (13)
N2—N3—C9120.18 (12)N2—C7—C8127.65 (13)
N2—N3—H1N3119.1 (15)C6—C7—C8106.44 (12)
C9—N3—H1N3120.6 (15)O1—C8—N1127.21 (14)
C9—N4—C10123.25 (13)O1—C8—C7126.20 (13)
C9—N4—H1N4120.3 (16)N1—C8—C7106.59 (13)
C10—N4—H1N4116.4 (16)N4—C9—N3116.09 (13)
C2—C1—C6121.61 (15)N4—C9—S1125.91 (11)
C2—C1—N1128.67 (15)N3—C9—S1118.00 (11)
C6—C1—N1109.72 (13)N4—C10—H10A109.5
C1—C2—C3117.20 (15)N4—C10—H10B109.5
C1—C2—H2A121.4H10A—C10—H10B109.5
C3—C2—H2A121.4N4—C10—H10C109.5
C4—C3—C2122.33 (14)H10A—C10—H10C109.5
C4—C3—H3A118.8H10B—C10—H10C109.5
C2—C3—H3A118.8C4—C11—H11A109.5
C3—C4—C5119.23 (14)C4—C11—H11B109.5
C3—C4—C11120.45 (14)H11A—C11—H11B109.5
C5—C4—C11120.31 (15)C4—C11—H11C109.5
C6—C5—C4119.07 (14)H11A—C11—H11C109.5
C6—C5—H5A120.5H11B—C11—H11C109.5
C4—C5—H5A120.5
C7—N2—N3—C9176.69 (13)N3—N2—C7—C6178.16 (13)
C8—N1—C1—C2178.42 (15)N3—N2—C7—C80.6 (2)
C8—N1—C1—C61.59 (17)C5—C6—C7—N22.0 (3)
C6—C1—C2—C30.3 (2)C1—C6—C7—N2177.54 (14)
N1—C1—C2—C3179.68 (14)C5—C6—C7—C8178.97 (15)
C1—C2—C3—C41.1 (2)C1—C6—C7—C81.48 (15)
C2—C3—C4—C51.3 (2)C1—N1—C8—O1179.56 (15)
C2—C3—C4—C11178.82 (15)C1—N1—C8—C70.58 (16)
C3—C4—C5—C60.1 (2)N2—C7—C8—O12.6 (2)
C11—C4—C5—C6179.99 (14)C6—C7—C8—O1178.43 (14)
C4—C5—C6—C11.2 (2)N2—C7—C8—N1178.43 (14)
C4—C5—C6—C7178.28 (15)C6—C7—C8—N10.57 (16)
C2—C1—C6—C51.5 (2)C10—N4—C9—N3179.39 (14)
N1—C1—C6—C5178.51 (13)C10—N4—C9—S11.4 (2)
C2—C1—C6—C7178.14 (13)N2—N3—C9—N40.19 (19)
N1—C1—C6—C71.87 (16)N2—N3—C9—S1179.14 (10)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.81 (2)2.03 (2)2.8319 (17)171 (2)
N3—H1N3···O10.84 (2)2.079 (19)2.7525 (17)136.9 (17)
N4—H1N4···S1ii0.80 (2)2.85 (2)3.5538 (13)148.5 (19)
C3—H3A···Cg2iii0.952.623.4165 (16)142
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1/2, z+1/2; (iii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC11H12N4OS
Mr248.31
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)6.2826 (2), 10.0341 (3), 19.1315 (5)
V3)1206.05 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.51 × 0.18 × 0.13
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.879, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
13743, 3780, 3463
Rint0.050
(sin θ/λ)max1)0.724
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.097, 1.07
No. of reflections3780
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.24
Absolute structureFlack (1983), with 1584 Friedel pairs
Absolute structure parameter0.08 (7)

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.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.81 (2)2.03 (2)2.8319 (17)171 (2)
N3—H1N3···O10.84 (2)2.079 (19)2.7525 (17)136.9 (17)
N4—H1N4···S1ii0.80 (2)2.85 (2)3.5538 (13)148.5 (19)
C3—H3A···Cg2iii0.952.623.4165 (16)142
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1/2, z+1/2; (iii) x+1/2, y+3/2, 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 an RU research 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 o955-o956
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