4-Methyl-N'-(2-oxoindolin-3-yl-idene)benzene-1-sulfono-hydrazide.

In the title compound, C(15)H(13)N(3)O(3)S, the C-S-N(H)-N linkage is non-planar, the torsion angle being -65.12 (13)° and the S atom showing a tetra-hedral environment. The compound has two almost planar fragments linked to the S atom: the isatin-derivative fragment [(C(8)H(5)NO)N-N(H)-] and the tolyl fragment [C(7)H(7)-] have maximum deviations from the mean plane through the non-H atoms of 0.0813 (13) and 0.0094 (16) Å, respectively, and make an inter-planar angle of 80.48 (3)°. In the crystal, mol-ecules are connected into inversion dimers via pairs of N-H⋯O hydrogen bonds. Additionally, the mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond.

Related literature

For the synthesis of isatin-3-tosyl­hydrazone, see: Cava et al. (1958 ▶). For the anti­fungal and anti­bacterial properties of isatin derivatives, including the title compound, see: Chohan et al. (2004 ▶).

Experimental

Crystal data

C15H13N3O3S

M = 315.35

Monoclinic,

a = 14.9050 (3) Å

b = 5.7849 (1) Å

c = 17.8112 (3) Å

β = 110.427 (1)°

V = 1439.18 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.56 × 0.16 × 0.10 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.877, T max = 0.976

15630 measured reflections

4204 independent reflections

3146 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.05

4204 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.44 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046605/nc2252sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046605/nc2252Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046605/nc2252Isup3.cml

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

C15H13N3O3S	F(000) = 656
Mr = 315.35	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Melting point: 476 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.9050 (3) Å	Cell parameters from 4508 reflections
b = 5.7849 (1) Å	θ = 2.9–26.0°
c = 17.8112 (3) Å	µ = 0.24 mm−1
β = 110.427 (1)°	T = 293 K
V = 1439.18 (5) Å3	Block, yellow
Z = 4	0.56 × 0.16 × 0.10 mm

Bruker X8 APEXII CCD area-detector diffractometer	4204 independent reflections
Radiation source: fine-focus sealed tube, Bruker X8 APEXII	3146 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→21
Tmin = 0.877, Tmax = 0.976	k = −8→5
15630 measured reflections	l = −25→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.4436P] where P = (Fo2 + 2Fc2)/3
4204 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.44 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
C3	0.11277 (11)	1.0172 (3)	0.32467 (9)	0.0394 (4)
H3	0.1057	1.1188	0.3627	0.047*
C11	0.53807 (13)	0.3670 (4)	0.17689 (12)	0.0566 (5)
H8	0.5908	0.3119	0.2187	0.068*
C12	0.54616 (13)	0.5683 (4)	0.13898 (12)	0.0527 (5)
C10	0.45279 (12)	0.2441 (3)	0.15401 (11)	0.0490 (4)
H7	0.4482	0.1086	0.1805	0.059*
C13	0.46719 (15)	0.6454 (4)	0.07640 (14)	0.0606 (5)
H9	0.4717	0.7815	0.0501	0.073*
C14	0.38184 (13)	0.5253 (3)	0.05197 (12)	0.0540 (5)
H10	0.3296	0.5786	0.0094	0.065*
C15	0.63816 (15)	0.7038 (5)	0.16498 (16)	0.0760 (7)
H11	0.6298	0.8449	0.1901	0.114*
H12	0.6553	0.7391	0.1191	0.114*
H13	0.6881	0.6138	0.2023	0.114*
H6	0.1551 (15)	0.431 (4)	0.0260 (12)	0.059 (6)*
H1	0.0168 (14)	1.043 (4)	0.0776 (12)	0.055 (6)*
S1	0.26748 (3)	0.16782 (7)	0.06008 (2)	0.03535 (12)
N3	0.18364 (9)	0.3472 (2)	0.06478 (8)	0.0352 (3)
N2	0.19062 (8)	0.4241 (2)	0.13897 (7)	0.0320 (3)
C8	0.08200 (10)	0.7533 (3)	0.07301 (8)	0.0305 (3)
O1	0.06596 (8)	0.71841 (19)	0.00121 (6)	0.0382 (3)
C9	0.37519 (11)	0.3244 (3)	0.09182 (9)	0.0347 (3)
N1	0.05136 (9)	0.9330 (2)	0.10573 (7)	0.0329 (3)
C7	0.14177 (10)	0.6049 (2)	0.14176 (8)	0.0292 (3)
C1	0.08633 (10)	0.9203 (2)	0.19011 (8)	0.0295 (3)
O3	0.23997 (9)	0.1214 (2)	−0.02344 (7)	0.0511 (3)
C5	0.17706 (11)	0.6607 (3)	0.29508 (9)	0.0353 (3)
H5	0.2115	0.5247	0.3121	0.042*
C2	0.07358 (11)	1.0743 (3)	0.24401 (9)	0.0351 (3)
H2	0.0400	1.2115	0.2272	0.042*
C6	0.13941 (10)	0.7169 (2)	0.21428 (8)	0.0298 (3)
C4	0.16212 (11)	0.8120 (3)	0.34970 (9)	0.0398 (4)
H4	0.1855	0.7755	0.4040	0.048*
O2	0.27543 (8)	−0.0145 (2)	0.11553 (8)	0.0481 (3)

	U11	U22	U33	U12	U13	U23
C3	0.0415 (8)	0.0398 (9)	0.0366 (8)	0.0005 (7)	0.0132 (7)	−0.0057 (7)
C11	0.0392 (9)	0.0670 (13)	0.0552 (11)	−0.0021 (9)	0.0060 (8)	−0.0073 (10)
C12	0.0403 (9)	0.0587 (12)	0.0630 (12)	−0.0114 (8)	0.0231 (8)	−0.0226 (10)
C10	0.0454 (9)	0.0506 (10)	0.0469 (10)	−0.0021 (8)	0.0109 (8)	0.0040 (8)
C13	0.0556 (12)	0.0479 (11)	0.0792 (15)	−0.0130 (9)	0.0247 (10)	0.0044 (10)
C14	0.0423 (9)	0.0485 (10)	0.0646 (12)	−0.0034 (8)	0.0105 (8)	0.0089 (9)
C15	0.0501 (12)	0.0853 (17)	0.0963 (18)	−0.0272 (12)	0.0300 (12)	−0.0305 (14)
S1	0.0344 (2)	0.0308 (2)	0.0424 (2)	−0.00097 (15)	0.01533 (16)	−0.00615 (15)
N3	0.0354 (7)	0.0364 (7)	0.0338 (7)	0.0062 (5)	0.0122 (5)	0.0009 (6)
N2	0.0333 (6)	0.0304 (6)	0.0335 (6)	0.0027 (5)	0.0133 (5)	0.0016 (5)
C8	0.0282 (6)	0.0315 (7)	0.0314 (7)	0.0007 (6)	0.0101 (5)	0.0068 (6)
O1	0.0424 (6)	0.0417 (6)	0.0294 (5)	0.0047 (5)	0.0111 (4)	0.0051 (5)
C9	0.0322 (7)	0.0333 (8)	0.0411 (8)	−0.0007 (6)	0.0158 (6)	−0.0063 (6)
N1	0.0360 (6)	0.0308 (6)	0.0313 (6)	0.0080 (5)	0.0109 (5)	0.0087 (5)
C7	0.0283 (6)	0.0292 (7)	0.0303 (7)	0.0008 (5)	0.0103 (5)	0.0059 (6)
C1	0.0287 (6)	0.0283 (7)	0.0317 (7)	0.0007 (5)	0.0107 (5)	0.0053 (6)
O3	0.0516 (7)	0.0557 (8)	0.0466 (7)	−0.0074 (6)	0.0177 (6)	−0.0220 (6)
C5	0.0342 (7)	0.0371 (8)	0.0319 (7)	0.0068 (6)	0.0081 (6)	0.0063 (6)
C2	0.0364 (7)	0.0288 (7)	0.0400 (8)	0.0040 (6)	0.0134 (6)	0.0024 (6)
C6	0.0288 (6)	0.0295 (7)	0.0315 (7)	0.0033 (5)	0.0109 (5)	0.0036 (6)
C4	0.0397 (8)	0.0460 (9)	0.0293 (7)	0.0023 (7)	0.0066 (6)	0.0014 (7)
O2	0.0449 (6)	0.0336 (6)	0.0689 (8)	0.0029 (5)	0.0239 (6)	0.0083 (6)

C3—C4	1.385 (2)	S1—N3	1.6488 (13)
C3—C2	1.389 (2)	S1—C9	1.7560 (15)
C3—H3	0.9300	N3—N2	1.3636 (17)
C11—C12	1.372 (3)	N3—H6	0.83 (2)
C11—C10	1.388 (3)	N2—C7	1.2853 (18)
C11—H8	0.9300	C8—O1	1.2329 (17)
C12—C13	1.383 (3)	C8—O1	1.2329 (17)
C12—C15	1.505 (3)	C8—N1	1.3471 (19)
C10—C9	1.373 (2)	C8—C7	1.5060 (19)
C10—H7	0.9300	N1—C1	1.4103 (18)
C13—C14	1.380 (3)	N1—H1	0.86 (2)
C13—H9	0.9300	C7—C6	1.456 (2)
C14—C9	1.383 (2)	C1—C2	1.371 (2)
C14—H10	0.9300	C1—C6	1.3991 (19)
C15—H11	0.9600	C5—C4	1.383 (2)
C15—H12	0.9600	C5—C6	1.3886 (19)
C15—H13	0.9600	C5—H5	0.9300
S1—O2	1.4212 (12)	C2—H2	0.9300
S1—O3	1.4239 (12)	C4—H4	0.9300
C4—C3—C2	121.40 (15)	S1—N3—H6	120.1 (14)
C4—C3—H3	119.3	C7—N2—N3	116.77 (12)
C2—C3—H3	119.3	O1—C8—N1	127.08 (13)
C12—C11—C10	121.27 (18)	O1—C8—N1	127.08 (13)
C12—C11—H8	119.4	O1—C8—C7	126.55 (14)
C10—C11—H8	119.4	O1—C8—C7	126.55 (14)
C11—C12—C13	118.32 (17)	N1—C8—C7	106.37 (12)
C11—C12—C15	121.2 (2)	C10—C9—C14	120.46 (16)
C13—C12—C15	120.5 (2)	C10—C9—S1	120.21 (13)
C9—C10—C11	119.39 (18)	C14—C9—S1	119.30 (13)
C9—C10—H7	120.3	C8—N1—C1	111.45 (12)
C11—C10—H7	120.3	C8—N1—H1	122.9 (13)
C14—C13—C12	121.56 (19)	C1—N1—H1	125.6 (13)
C14—C13—H9	119.2	N2—C7—C6	125.84 (13)
C12—C13—H9	119.2	N2—C7—C8	127.94 (13)
C13—C14—C9	118.99 (18)	C6—C7—C8	106.08 (12)
C13—C14—H10	120.5	C2—C1—C6	122.19 (13)
C9—C14—H10	120.5	C2—C1—N1	128.49 (13)
C12—C15—H11	109.5	C6—C1—N1	109.32 (12)
C12—C15—H12	109.5	C4—C5—C6	118.32 (14)
H11—C15—H12	109.5	C4—C5—H5	120.8
C12—C15—H13	109.5	C6—C5—H5	120.8
H11—C15—H13	109.5	C1—C2—C3	117.32 (14)
H12—C15—H13	109.5	C1—C2—H2	121.3
O2—S1—O3	120.64 (8)	C3—C2—H2	121.3
O2—S1—N3	108.22 (7)	C5—C6—C1	119.77 (13)
O3—S1—N3	102.99 (7)	C5—C6—C7	133.54 (13)
O2—S1—C9	108.30 (7)	C1—C6—C7	106.69 (12)
O3—S1—C9	109.34 (8)	C5—C4—C3	120.90 (14)
N3—S1—C9	106.44 (7)	C5—C4—H4	119.5
N2—N3—S1	116.86 (10)	C3—C4—H4	119.5
N2—N3—H6	117.5 (14)
C10—C11—C12—C13	−0.7 (3)	N3—N2—C7—C6	−179.42 (13)
C10—C11—C12—C15	178.77 (19)	N3—N2—C7—C8	−4.3 (2)
C12—C11—C10—C9	0.5 (3)	O1—C8—C7—N2	4.0 (2)
C11—C12—C13—C14	0.1 (3)	O1—C8—C7—N2	4.0 (2)
C15—C12—C13—C14	−179.4 (2)	N1—C8—C7—N2	−174.84 (14)
C12—C13—C14—C9	0.7 (3)	O1—C8—C7—C6	179.91 (14)
O2—S1—N3—N2	51.10 (13)	O1—C8—C7—C6	179.91 (14)
O3—S1—N3—N2	179.90 (11)	N1—C8—C7—C6	1.06 (15)
C9—S1—N3—N2	−65.12 (13)	C8—N1—C1—C2	177.47 (14)
S1—N3—N2—C7	162.65 (11)	C8—N1—C1—C6	−2.60 (16)
N1—C8—O1—O1	0.00 (10)	C6—C1—C2—C3	−2.3 (2)
C7—C8—O1—O1	0.00 (14)	N1—C1—C2—C3	177.61 (14)
C11—C10—C9—C14	0.3 (3)	C4—C3—C2—C1	−0.5 (2)
C11—C10—C9—S1	178.32 (14)	C4—C5—C6—C1	−1.2 (2)
C13—C14—C9—C10	−0.9 (3)	C4—C5—C6—C7	178.95 (15)
C13—C14—C9—S1	−178.95 (16)	C2—C1—C6—C5	3.2 (2)
O2—S1—C9—C10	8.34 (16)	N1—C1—C6—C5	−176.70 (13)
O3—S1—C9—C10	−124.90 (15)	C2—C1—C6—C7	−176.92 (13)
N3—S1—C9—C10	124.50 (14)	N1—C1—C6—C7	3.15 (15)
O2—S1—C9—C14	−173.62 (14)	N2—C7—C6—C5	−6.7 (3)
O3—S1—C9—C14	53.14 (16)	C8—C7—C6—C5	177.26 (16)
N3—S1—C9—C14	−57.46 (15)	N2—C7—C6—C1	173.44 (14)
O1—C8—N1—C1	−177.97 (14)	C8—C7—C6—C1	−2.56 (15)
O1—C8—N1—C1	−177.97 (14)	C6—C5—C4—C3	−1.5 (2)
C7—C8—N1—C1	0.88 (16)	C2—C3—C4—C5	2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H6···O1	0.83 (2)	2.08 (2)	2.7539 (17)	138.3 (19)
N1—H1···O1i	0.86 (2)	2.04 (2)	2.9029 (16)	172.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H6⋯O1	0.83 (2)	2.08 (2)	2.7539 (17)	138.3 (19)
N1—H1⋯O1i	0.86 (2)	2.04 (2)	2.9029 (16)	172.9 (18)

Symmetry code: (i) .