4-(2-Ethyl-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

The title compound, C(17)H(16)N(4)OS, is stabilized in the form of a two-dimensional polymeric network due to inter-molecular N-H⋯S and N-H⋯O hydrogen bonds. An intra-molecular N-H⋯N hydrogen bond forms an S(5) ring, whereas inter-actions of the N-H⋯O and C-H⋯S types complete S(6) ring motifs. π-π inter-actions with a centroid-centroid distance of 3.6514 (10) Å are found between the ethyl-substituted benzene ring and the heterocyclic ring of the isatin derivative.

Related literature

For the preparation of biologically important N 4-aryl­substituted isatin-3-thio­semicarbazones, see: Pervez et al. (2007 ▶). For a related structure, see: Pervez et al. (2010 ▶): For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H16N4OS

M = 324.40

Monoclinic,

a = 25.6769 (7) Å

b = 7.4340 (2) Å

c = 16.6548 (5) Å

β = 96.248 (1)°

V = 3160.22 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.952

11310 measured reflections

2823 independent reflections

2400 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.04

2823 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021264/bq2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021264/bq2219Isup2.hkl

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

C17H16N4OS	F(000) = 1360
Mr = 324.40	Dx = 1.364 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2400 reflections
a = 25.6769 (7) Å	θ = 2.9–25.3°
b = 7.4340 (2) Å	µ = 0.22 mm−1
c = 16.6548 (5) Å	T = 296 K
β = 96.248 (1)°	Prism, yellow
V = 3160.22 (15) Å3	0.32 × 0.24 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2823 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.9°
ω scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→8
Tmin = 0.942, Tmax = 0.952	l = −19→19
11310 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0406P)2 + 2.640P] where P = (Fo2 + 2Fc2)/3
2823 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.23890 (2)	−0.14366 (7)	0.38931 (2)	0.0442 (2)
O1	0.06872 (4)	−0.02675 (19)	0.27866 (7)	0.0479 (4)
N1	0.02670 (5)	0.0792 (2)	0.15804 (8)	0.0442 (5)
N2	0.16415 (5)	0.02887 (19)	0.19012 (8)	0.0349 (4)
N3	0.17539 (5)	−0.03419 (19)	0.26578 (8)	0.0372 (4)
N4	0.26102 (5)	−0.0071 (2)	0.24633 (8)	0.0393 (4)
C1	0.06870 (6)	0.0291 (2)	0.20906 (10)	0.0381 (5)
C2	0.04184 (6)	0.1426 (2)	0.08419 (10)	0.0391 (5)
C3	0.01121 (7)	0.2144 (3)	0.01920 (11)	0.0516 (6)
C4	0.03640 (8)	0.2668 (3)	−0.04645 (11)	0.0547 (7)
C5	0.09005 (8)	0.2485 (3)	−0.04709 (11)	0.0495 (6)
C6	0.12070 (7)	0.1798 (2)	0.01934 (9)	0.0409 (5)
C7	0.09608 (6)	0.1274 (2)	0.08544 (9)	0.0341 (5)
C8	0.11566 (6)	0.0567 (2)	0.16408 (9)	0.0333 (5)
C9	0.22671 (6)	−0.0580 (2)	0.29697 (9)	0.0342 (5)
C10	0.31682 (6)	−0.0090 (2)	0.25921 (10)	0.0365 (5)
C11	0.34405 (6)	−0.0684 (2)	0.19598 (10)	0.0392 (5)
C12	0.39859 (7)	−0.0623 (3)	0.20944 (12)	0.0511 (7)
C13	0.42445 (7)	0.0001 (3)	0.28101 (13)	0.0585 (7)
C14	0.39670 (7)	0.0588 (3)	0.34154 (12)	0.0546 (7)
C15	0.34255 (7)	0.0550 (3)	0.33083 (11)	0.0452 (6)
C16	0.31486 (8)	−0.1327 (3)	0.11775 (11)	0.0495 (6)
C17	0.34737 (10)	−0.2230 (3)	0.05832 (13)	0.0717 (9)
H1	−0.00519	0.07323	0.16915	0.0531*
H3	−0.02481	0.22716	0.01929	0.0619*
H3A	0.15051	−0.05950	0.29454	0.0446*
H4	0.01673	0.31566	−0.09139	0.0656*
H4A	0.24765	0.03177	0.19999	0.0471*
H5	0.10561	0.28267	−0.09261	0.0594*
H6	0.15681	0.16924	0.01957	0.0490*
H12	0.41813	−0.10153	0.16896	0.0613*
H13	0.46088	0.00228	0.28809	0.0702*
H14	0.41418	0.10101	0.38969	0.0655*
H15	0.32347	0.09524	0.37168	0.0543*
H16A	0.29714	−0.03025	0.09104	0.0595*
H16B	0.28807	−0.21671	0.13056	0.0595*
H17A	0.37156	−0.13760	0.04015	0.1076*
H17B	0.32467	−0.26665	0.01289	0.1076*
H17C	0.36643	−0.32188	0.08436	0.1076*

	U11	U22	U33	U12	U13	U23
S1	0.0421 (3)	0.0538 (3)	0.0371 (2)	0.0059 (2)	0.0058 (2)	0.0088 (2)
O1	0.0369 (6)	0.0701 (9)	0.0379 (7)	0.0024 (6)	0.0097 (5)	0.0099 (6)
N1	0.0265 (7)	0.0667 (10)	0.0396 (8)	−0.0015 (7)	0.0045 (6)	0.0036 (7)
N2	0.0306 (7)	0.0406 (8)	0.0334 (7)	0.0011 (6)	0.0036 (5)	0.0002 (6)
N3	0.0290 (7)	0.0488 (9)	0.0345 (7)	0.0018 (6)	0.0061 (5)	0.0052 (6)
N4	0.0294 (7)	0.0548 (9)	0.0339 (7)	0.0038 (6)	0.0043 (5)	0.0074 (6)
C1	0.0321 (8)	0.0449 (10)	0.0379 (9)	−0.0012 (7)	0.0060 (7)	−0.0007 (7)
C2	0.0345 (8)	0.0455 (10)	0.0368 (8)	−0.0021 (7)	0.0013 (7)	−0.0010 (7)
C3	0.0384 (9)	0.0649 (13)	0.0495 (10)	0.0047 (9)	−0.0042 (8)	0.0045 (9)
C4	0.0584 (12)	0.0610 (13)	0.0418 (10)	0.0041 (10)	−0.0071 (9)	0.0092 (9)
C5	0.0600 (12)	0.0511 (12)	0.0378 (9)	−0.0038 (9)	0.0069 (8)	0.0048 (8)
C6	0.0425 (9)	0.0449 (10)	0.0356 (9)	−0.0032 (8)	0.0063 (7)	−0.0013 (7)
C7	0.0331 (8)	0.0358 (9)	0.0329 (8)	−0.0007 (7)	0.0020 (6)	−0.0035 (7)
C8	0.0304 (8)	0.0374 (9)	0.0325 (8)	−0.0002 (7)	0.0049 (6)	−0.0018 (7)
C9	0.0314 (8)	0.0344 (9)	0.0372 (9)	0.0042 (6)	0.0053 (6)	−0.0032 (7)
C10	0.0317 (8)	0.0386 (9)	0.0394 (9)	0.0028 (7)	0.0054 (7)	0.0084 (7)
C11	0.0408 (9)	0.0359 (9)	0.0424 (9)	0.0052 (7)	0.0118 (7)	0.0102 (7)
C12	0.0419 (10)	0.0567 (12)	0.0583 (12)	0.0099 (9)	0.0214 (9)	0.0154 (9)
C13	0.0308 (9)	0.0763 (15)	0.0682 (13)	−0.0005 (9)	0.0051 (9)	0.0178 (11)
C14	0.0410 (10)	0.0684 (14)	0.0523 (11)	−0.0099 (9)	−0.0040 (8)	0.0095 (10)
C15	0.0391 (9)	0.0541 (11)	0.0426 (10)	−0.0009 (8)	0.0048 (7)	0.0029 (8)
C16	0.0587 (11)	0.0465 (11)	0.0448 (10)	0.0051 (9)	0.0119 (8)	0.0032 (8)
C17	0.0976 (17)	0.0655 (15)	0.0572 (13)	−0.0001 (13)	0.0317 (12)	−0.0070 (11)

S1—C9	1.6625 (15)	C10—C15	1.384 (2)
O1—C1	1.231 (2)	C11—C16	1.508 (3)
N1—C1	1.351 (2)	C11—C12	1.395 (2)
N1—C2	1.411 (2)	C12—C13	1.380 (3)
N2—N3	1.3460 (19)	C13—C14	1.368 (3)
N2—C8	1.290 (2)	C14—C15	1.383 (3)
N3—C9	1.374 (2)	C16—C17	1.519 (3)
N4—C9	1.339 (2)	C3—H3	0.9300
N4—C10	1.426 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3A	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C12—H12	0.9300
C1—C8	1.501 (2)	C13—H13	0.9300
C2—C7	1.395 (2)	C14—H14	0.9300
C2—C3	1.375 (2)	C15—H15	0.9300
C3—C4	1.386 (3)	C16—H16A	0.9700
C4—C5	1.386 (3)	C16—H16B	0.9700
C5—C6	1.384 (2)	C17—H17A	0.9600
C6—C7	1.384 (2)	C17—H17B	0.9600
C7—C8	1.450 (2)	C17—H17C	0.9600
C10—C11	1.398 (2)
S1···C15	3.283 (2)	C1···H1iii	2.7600
S1···N4i	3.5220 (15)	C1···H3A	2.4900
S1···H15	2.8500	C5···H17Avii	3.0500
S1···H6ii	3.1900	C9···H15	2.8900
S1···H4Ai	2.8700	C9···H16Biv	2.8500
S1···H16Ai	3.0500	C12···H5vii	2.8400
O1···N2	3.0226 (17)	C12···H17A	2.8800
O1···N3	2.7711 (17)	C12···H17C	2.8900
O1···C5ii	3.331 (2)	C16···H4A	2.6200
O1···N1iii	2.8805 (17)	C17···H12	2.6000
O1···H1iii	2.0700	H1···O1iii	2.0700
O1···H3A	2.1000	H1···C1iii	2.7600
N1···O1iii	2.8805 (17)	H3A···O1	2.1000
N2···O1	3.0226 (17)	H3A···C1	2.4900
N2···N4	2.5745 (18)	H4A···N2	2.1300
N3···O1	2.7711 (17)	H4A···C16	2.6200
N4···C9iv	3.437 (2)	H4A···H16A	2.3700
N4···N2	2.5745 (18)	H4A···H16B	2.4700
N4···S1iv	3.5220 (15)	H4A···S1iv	2.8700
N2···H4A	2.1300	H5···C12vii	2.8400
N4···H16B	2.6300	H6···S1vi	3.1900
N4···H16A	2.8500	H12···C17	2.6000
C1···C13iv	3.509 (3)	H12···H17A	2.3500
C1···C12iv	3.395 (3)	H12···H17C	2.4500
C2···C3v	3.370 (3)	H13···H13viii	2.4900
C2···C13iv	3.526 (3)	H15···S1	2.8500
C3···C3v	3.290 (3)	H15···C9	2.8900
C3···C2v	3.370 (3)	H16A···N4	2.8500
C5···O1vi	3.331 (2)	H16A···H4A	2.3700
C7···C14iv	3.428 (3)	H16A···S1iv	3.0500
C8···C12iv	3.572 (3)	H16B···N4	2.6300
C9···N4i	3.437 (2)	H16B···H4A	2.4700
C12···C8i	3.572 (3)	H16B···C9i	2.8500
C12···C1i	3.395 (3)	H17A···C12	2.8800
C13···C2i	3.526 (3)	H17A···H12	2.3500
C13···C1i	3.509 (3)	H17A···C5vii	3.0500
C14···C7i	3.428 (3)	H17C···C12	2.8900
C15···S1	3.283 (2)	H17C···H12	2.4500
C1—N1—C2	111.33 (13)	C12—C11—C16	123.02 (16)
N3—N2—C8	118.13 (13)	C11—C12—C13	122.01 (17)
N2—N3—C9	119.86 (13)	C12—C13—C14	120.24 (17)
C9—N4—C10	128.46 (14)	C13—C14—C15	119.71 (18)
C2—N1—H1	124.00	C10—C15—C14	119.83 (17)
C1—N1—H1	124.00	C11—C16—C17	116.51 (17)
C9—N3—H3A	120.00	C2—C3—H3	121.00
N2—N3—H3A	120.00	C4—C3—H3	121.00
C9—N4—H4A	116.00	C3—C4—H4	119.00
C10—N4—H4A	116.00	C5—C4—H4	119.00
O1—C1—N1	127.14 (14)	C4—C5—H5	120.00
O1—C1—C8	126.71 (14)	C6—C5—H5	120.00
N1—C1—C8	106.14 (13)	C5—C6—H6	121.00
N1—C2—C7	109.23 (13)	C7—C6—H6	121.00
C3—C2—C7	121.86 (15)	C11—C12—H12	119.00
N1—C2—C3	128.89 (15)	C13—C12—H12	119.00
C2—C3—C4	117.02 (17)	C12—C13—H13	120.00
C3—C4—C5	121.90 (18)	C14—C13—H13	120.00
C4—C5—C6	120.63 (17)	C13—C14—H14	120.00
C5—C6—C7	118.08 (17)	C15—C14—H14	120.00
C2—C7—C6	120.47 (15)	C10—C15—H15	120.00
C2—C7—C8	106.88 (13)	C14—C15—H15	120.00
C6—C7—C8	132.64 (15)	C11—C16—H16A	108.00
N2—C8—C7	126.10 (14)	C11—C16—H16B	108.00
N2—C8—C1	127.49 (14)	C17—C16—H16A	108.00
C1—C8—C7	106.38 (13)	C17—C16—H16B	108.00
S1—C9—N3	118.38 (12)	H16A—C16—H16B	107.00
S1—C9—N4	128.35 (12)	C16—C17—H17A	109.00
N3—C9—N4	113.27 (13)	C16—C17—H17B	109.00
C11—C10—C15	121.82 (15)	C16—C17—H17C	109.00
N4—C10—C15	120.28 (15)	H17A—C17—H17B	109.00
N4—C10—C11	117.83 (14)	H17A—C17—H17C	109.00
C10—C11—C12	116.40 (15)	H17B—C17—H17C	109.00
C10—C11—C16	120.58 (15)
C1—N1—C2—C3	−176.03 (18)	C2—C3—C4—C5	−0.1 (3)
C2—N1—C1—O1	177.74 (16)	C3—C4—C5—C6	−1.3 (3)
C2—N1—C1—C8	−1.78 (17)	C4—C5—C6—C7	1.1 (3)
C1—N1—C2—C7	2.28 (18)	C5—C6—C7—C8	−177.87 (17)
N3—N2—C8—C7	178.61 (14)	C5—C6—C7—C2	0.5 (2)
C8—N2—N3—C9	−177.12 (14)	C2—C7—C8—N2	−177.51 (15)
N3—N2—C8—C1	0.9 (2)	C6—C7—C8—N2	1.1 (3)
N2—N3—C9—S1	−177.65 (12)	C6—C7—C8—C1	179.21 (16)
N2—N3—C9—N4	2.2 (2)	C2—C7—C8—C1	0.65 (16)
C10—N4—C9—S1	−1.7 (3)	N4—C10—C11—C12	177.69 (16)
C9—N4—C10—C15	−45.5 (2)	N4—C10—C11—C16	−1.6 (2)
C10—N4—C9—N3	178.48 (15)	C15—C10—C11—C12	1.0 (2)
C9—N4—C10—C11	137.74 (17)	C15—C10—C11—C16	−178.32 (17)
O1—C1—C8—N2	−0.7 (3)	N4—C10—C15—C14	−177.59 (18)
O1—C1—C8—C7	−178.83 (16)	C11—C10—C15—C14	−0.9 (3)
N1—C1—C8—N2	178.80 (16)	C10—C11—C12—C13	−0.4 (3)
N1—C1—C8—C7	0.68 (16)	C16—C11—C12—C13	178.81 (19)
N1—C2—C3—C4	179.90 (17)	C10—C11—C16—C17	−170.19 (16)
C7—C2—C3—C4	1.8 (3)	C12—C11—C16—C17	10.6 (3)
N1—C2—C7—C6	179.51 (14)	C11—C12—C13—C14	−0.1 (3)
N1—C2—C7—C8	−1.72 (17)	C12—C13—C14—C15	0.2 (3)
C3—C2—C7—C6	−2.0 (2)	C13—C14—C15—C10	0.4 (3)
C3—C2—C7—C8	176.74 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1iii	0.8600	2.0700	2.8805 (17)	157.00
N3—H3A···O1	0.8600	2.1000	2.7711 (17)	134.00
N4—H4A···N2	0.8600	2.1300	2.5745 (18)	111.00
N4—H4A···S1iv	0.8600	2.8700	3.5220 (15)	133.00
C15—H15···S1	0.9300	2.8500	3.283 (2)	110.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.07	2.88 (17)	157
N3—H3A⋯O1	0.86	2.10	2.7711 (17)	134
N4—H4A⋯N2	0.86	2.13	2.5745 (18)	111
N4—H4A⋯S1ii	0.86	2.87	3.5220 (15)	133
C15—H15⋯S1	0.93	2.85	3.283 (2)	110

Symmetry codes: (i) ; (ii) .