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

In the title compound, C(16)H(14)N(4)OS, the dihedral angle between the nine-membered 5-methyl-indolin-2-one ring system and the benzene ring is 10.21 (7)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present within the N-N-C-N chain between the ring systems. In the crystal, mol-ecules form centrosymmetric cyclic dimers through pairs of N-H⋯O hydrogen bonds [graph set R(2) (2)(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 n class="Chemical">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

C16H14N4n class="Chemical">OS

M = 310.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.123

S = 1.06

4645 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

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/S1600536811049154/zs2160sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049154/zs2160Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049154/zs2160Isup3.cml

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

C16H14N4OS	F(000) = 648
Mr = 310.37	Dx = 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

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

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(Fo2) + (0.044P)2 + 0.9076P] where P = (Fo2 + 2Fc2)/3
4645 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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	0.07706 (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)*

	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)

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)

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

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) .