(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(12)N(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules 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 inter-action into a three-dimensional network.

Related literature

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

Crystal data

C11H12N4OS

M = 248.31

Orthorhombic,

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 ▶) T min = 0.879, T max = 0.967

13743 measured reflections

3780 independent reflections

3463 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 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 ▶), with 1584 Friedel pairs

Flack parameter: −0.08 (7)

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005417/is5066sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005417/is5066Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005417/is5066Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H12N4OS	Dx = 1.368 Mg m−3
Mr = 248.31	Melting point = 551.7–552.2 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5511 reflections
a = 6.2826 (2) Å	θ = 2.3–30.7°
b = 10.0341 (3) Å	µ = 0.26 mm−1
c = 19.1315 (5) Å	T = 100 K
V = 1206.05 (6) Å3	Block, orange
Z = 4	0.51 × 0.18 × 0.13 mm
F(000) = 520

Bruker APEXII CCD diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 31.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
Tmin = 0.879, Tmax = 0.967	k = −14→13
13743 measured reflections	l = −26→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H 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 reflections	Δρmax = 0.32 e Å−3
168 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), with 1584 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.08 (7)

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.

	x	y	z	Uiso*/Ueq
S1	−0.25429 (6)	0.29169 (3)	0.213725 (19)	0.02077 (10)
O1	0.31886 (18)	0.26735 (11)	0.06564 (6)	0.0214 (2)
N1	0.6103 (2)	0.39581 (13)	0.03384 (7)	0.0191 (3)
N2	0.2245 (2)	0.50945 (11)	0.15475 (6)	0.0159 (2)
N3	0.0861 (2)	0.40757 (13)	0.16284 (7)	0.0171 (2)
N4	−0.1126 (2)	0.54025 (13)	0.23530 (7)	0.0181 (2)
C1	0.6888 (2)	0.52394 (15)	0.05069 (8)	0.0170 (3)
C2	0.8718 (2)	0.58576 (17)	0.02731 (8)	0.0206 (3)
H2A	0.9661	0.5427	−0.0042	0.025*
C3	0.9124 (2)	0.71447 (17)	0.05206 (8)	0.0217 (3)
H3A	1.0386	0.7586	0.0374	0.026*
C4	0.7740 (2)	0.78049 (15)	0.09758 (7)	0.0202 (3)
C5	0.5903 (2)	0.71534 (15)	0.12059 (7)	0.0175 (3)
H5A	0.4945	0.7585	0.1516	0.021*
C6	0.5498 (2)	0.58673 (15)	0.09747 (7)	0.0157 (3)
C7	0.3812 (2)	0.49169 (14)	0.11202 (7)	0.0158 (3)
C8	0.4287 (2)	0.37009 (15)	0.06883 (8)	0.0175 (3)
C9	−0.0900 (2)	0.42245 (14)	0.20479 (7)	0.0163 (3)
C10	−0.2903 (2)	0.57322 (17)	0.28065 (9)	0.0246 (3)
H10A	−0.3009	0.6702	0.2853	0.037*
H10B	−0.2675	0.5333	0.3268	0.037*
H10C	−0.4223	0.5383	0.2604	0.037*
C11	0.8227 (3)	0.92103 (18)	0.12193 (9)	0.0288 (4)
H11A	0.9767	0.9361	0.1204	0.043*
H11B	0.7716	0.9327	0.1699	0.043*
H11C	0.7511	0.9851	0.0912	0.043*
H1N1	0.675 (4)	0.345 (2)	0.0091 (12)	0.030 (6)*
H1N3	0.105 (3)	0.337 (2)	0.1401 (10)	0.022 (5)*
H1N4	−0.027 (4)	0.598 (2)	0.2289 (11)	0.028 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01781 (16)	0.01833 (15)	0.02616 (18)	−0.00367 (14)	0.00191 (16)	0.00281 (13)
O1	0.0245 (5)	0.0189 (5)	0.0207 (5)	−0.0035 (4)	−0.0012 (4)	−0.0036 (4)
N1	0.0210 (6)	0.0189 (6)	0.0173 (6)	0.0018 (5)	0.0025 (5)	−0.0022 (5)
N2	0.0162 (6)	0.0145 (5)	0.0171 (5)	−0.0021 (4)	−0.0010 (5)	0.0021 (4)
N3	0.0167 (6)	0.0147 (5)	0.0200 (6)	−0.0019 (5)	0.0022 (5)	−0.0016 (4)
N4	0.0145 (5)	0.0195 (6)	0.0204 (6)	−0.0004 (5)	0.0015 (5)	−0.0009 (5)
C1	0.0175 (6)	0.0185 (6)	0.0149 (6)	0.0012 (5)	−0.0009 (5)	0.0020 (5)
C2	0.0171 (7)	0.0255 (7)	0.0191 (7)	0.0031 (6)	0.0023 (5)	0.0038 (6)
C3	0.0162 (6)	0.0277 (7)	0.0213 (7)	−0.0036 (6)	−0.0010 (5)	0.0069 (6)
C4	0.0211 (7)	0.0220 (6)	0.0174 (6)	−0.0062 (6)	−0.0035 (5)	0.0031 (5)
C5	0.0180 (6)	0.0185 (6)	0.0161 (6)	−0.0013 (6)	−0.0002 (5)	0.0003 (5)
C6	0.0148 (6)	0.0184 (6)	0.0140 (6)	0.0005 (5)	−0.0001 (5)	0.0013 (5)
C7	0.0167 (6)	0.0164 (6)	0.0143 (6)	−0.0005 (5)	−0.0021 (5)	−0.0008 (5)
C8	0.0197 (7)	0.0175 (6)	0.0154 (6)	0.0015 (5)	−0.0018 (5)	−0.0015 (5)
C9	0.0151 (6)	0.0170 (6)	0.0169 (6)	0.0004 (5)	−0.0026 (5)	0.0019 (5)
C10	0.0195 (7)	0.0294 (7)	0.0251 (7)	0.0036 (6)	0.0031 (6)	−0.0041 (6)
C11	0.0322 (8)	0.0273 (8)	0.0271 (8)	−0.0129 (7)	−0.0012 (7)	−0.0017 (7)

S1—C9	1.6781 (15)	C2—H2A	0.9500
O1—C8	1.2419 (18)	C3—C4	1.398 (2)
N1—C8	1.348 (2)	C3—H3A	0.9500
N1—C1	1.414 (2)	C4—C5	1.398 (2)
N1—H1N1	0.81 (2)	C4—C11	1.516 (2)
N2—C7	1.2920 (19)	C5—C6	1.388 (2)
N2—N3	1.3510 (17)	C5—H5A	0.9500
N3—C9	1.3749 (19)	C6—C7	1.452 (2)
N3—H1N3	0.84 (2)	C7—C8	1.503 (2)
N4—C9	1.3259 (19)	C10—H10A	0.9800
N4—C10	1.4520 (19)	C10—H10B	0.9800
N4—H1N4	0.80 (2)	C10—H10C	0.9800
C1—C2	1.381 (2)	C11—H11A	0.9800
C1—C6	1.400 (2)	C11—H11B	0.9800
C2—C3	1.399 (2)	C11—H11C	0.9800
C8—N1—C1	110.85 (13)	C5—C6—C1	120.52 (14)
C8—N1—H1N1	127.0 (16)	C5—C6—C7	133.10 (14)
C1—N1—H1N1	122.0 (16)	C1—C6—C7	106.37 (13)
C7—N2—N3	117.30 (12)	N2—C7—C6	125.90 (13)
N2—N3—C9	120.18 (12)	N2—C7—C8	127.65 (13)
N2—N3—H1N3	119.1 (15)	C6—C7—C8	106.44 (12)
C9—N3—H1N3	120.6 (15)	O1—C8—N1	127.21 (14)
C9—N4—C10	123.25 (13)	O1—C8—C7	126.20 (13)
C9—N4—H1N4	120.3 (16)	N1—C8—C7	106.59 (13)
C10—N4—H1N4	116.4 (16)	N4—C9—N3	116.09 (13)
C2—C1—C6	121.61 (15)	N4—C9—S1	125.91 (11)
C2—C1—N1	128.67 (15)	N3—C9—S1	118.00 (11)
C6—C1—N1	109.72 (13)	N4—C10—H10A	109.5
C1—C2—C3	117.20 (15)	N4—C10—H10B	109.5
C1—C2—H2A	121.4	H10A—C10—H10B	109.5
C3—C2—H2A	121.4	N4—C10—H10C	109.5
C4—C3—C2	122.33 (14)	H10A—C10—H10C	109.5
C4—C3—H3A	118.8	H10B—C10—H10C	109.5
C2—C3—H3A	118.8	C4—C11—H11A	109.5
C3—C4—C5	119.23 (14)	C4—C11—H11B	109.5
C3—C4—C11	120.45 (14)	H11A—C11—H11B	109.5
C5—C4—C11	120.31 (15)	C4—C11—H11C	109.5
C6—C5—C4	119.07 (14)	H11A—C11—H11C	109.5
C6—C5—H5A	120.5	H11B—C11—H11C	109.5
C4—C5—H5A	120.5
C7—N2—N3—C9	−176.69 (13)	N3—N2—C7—C6	−178.16 (13)
C8—N1—C1—C2	178.42 (15)	N3—N2—C7—C8	0.6 (2)
C8—N1—C1—C6	−1.59 (17)	C5—C6—C7—N2	−2.0 (3)
C6—C1—C2—C3	−0.3 (2)	C1—C6—C7—N2	177.54 (14)
N1—C1—C2—C3	179.68 (14)	C5—C6—C7—C8	178.97 (15)
C1—C2—C3—C4	−1.1 (2)	C1—C6—C7—C8	−1.48 (15)
C2—C3—C4—C5	1.3 (2)	C1—N1—C8—O1	179.56 (15)
C2—C3—C4—C11	−178.82 (15)	C1—N1—C8—C7	0.58 (16)
C3—C4—C5—C6	−0.1 (2)	N2—C7—C8—O1	2.6 (2)
C11—C4—C5—C6	−179.99 (14)	C6—C7—C8—O1	−178.43 (14)
C4—C5—C6—C1	−1.2 (2)	N2—C7—C8—N1	−178.43 (14)
C4—C5—C6—C7	178.28 (15)	C6—C7—C8—N1	0.57 (16)
C2—C1—C6—C5	1.5 (2)	C10—N4—C9—N3	179.39 (14)
N1—C1—C6—C5	−178.51 (13)	C10—N4—C9—S1	−1.4 (2)
C2—C1—C6—C7	−178.14 (13)	N2—N3—C9—N4	0.19 (19)
N1—C1—C6—C7	1.87 (16)	N2—N3—C9—S1	−179.14 (10)

D—H···A	D—H	H···A	D···A	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—H3A···Cg2iii	0.95	2.62	3.4165 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	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—H3A⋯Cg2iii	0.95	2.62	3.4165 (16)	142

Symmetry codes: (i) ; (ii) ; (iii) .