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

In the title compound, C(15)H(11)N(5)O(3)S, intra-molecular N-H⋯N hydrogen bonding forms an S(5) ring motif, whereas N-H⋯O and C-H⋯S inter-actions type complete S(6) ring motifs. The 2-oxoindoline and 3-methoxy-phenyl rings are almost planar, with r.m.s. deviations of 0.0178 and 0.0149 Å, respectively, and form a dihedral angle of 33.59 (3)°. In the crystal, mol-ecules are inter-linked through the nitro groups in an end-to-end fashion via N-H⋯O and C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C15H11N5O3S

M = 341.35

Orthorhombic,

a = 18.5545 (10) Å

b = 15.3852 (8) Å

c = 5.3367 (4) Å

V = 1523.44 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.24 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.966

7285 measured reflections

2751 independent reflections

1957 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.00

2751 reflections

217 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 992 Friedel pairs

Flack parameter: −0.05 (11)

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/S1600536810017964/bq2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017964/bq2210Isup2.hkl

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

C15H11N5O3S	F(000) = 704
Mr = 341.35	Dx = 1.488 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2751 reflections
a = 18.5545 (10) Å	θ = 2.6–26.5°
b = 15.3852 (8) Å	µ = 0.24 mm−1
c = 5.3367 (4) Å	T = 296 K
V = 1523.44 (16) Å3	Prism, light yellow
Z = 4	0.24 × 0.16 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	1957 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 7.80 pixels mm-1	θmax = 26.5°, θmin = 2.6°
ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→18
Tmin = 0.957, Tmax = 0.966	l = −6→5
7285 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2751 reflections	Δρmax = 0.16 e Å−3
217 parameters	Δρmin = −0.27 e Å−3
1 restraint	Absolute structure: Flack (1983), 992 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.22195 (4)	0.31899 (4)	−0.2161 (2)	0.0691 (3)
O1	0.38865 (11)	0.31688 (13)	0.4271 (5)	0.0693 (6)
O2	0.04767 (14)	0.25693 (14)	−0.7833 (6)	0.0987 (11)
O3	0.01628 (11)	0.14340 (14)	−0.9884 (5)	0.0691 (6)
N1	0.42883 (11)	0.21951 (15)	0.7293 (5)	0.0584 (7)
H1	0.4577	0.2529	0.8109	0.070*
N2	0.29869 (10)	0.15983 (12)	0.2774 (5)	0.0462 (5)
N3	0.28351 (11)	0.23206 (14)	0.1419 (5)	0.0511 (6)
H3	0.3036	0.2806	0.1808	0.061*
N4	0.21013 (11)	0.14865 (14)	−0.0938 (5)	0.0485 (6)
H4A	0.2223	0.1111	0.0179	0.058*
N5	0.04756 (12)	0.17858 (16)	−0.8135 (5)	0.0573 (7)
C1	0.38904 (15)	0.24541 (19)	0.5275 (6)	0.0526 (8)
C2	0.34565 (13)	0.16630 (16)	0.4526 (6)	0.0443 (6)
C3	0.36668 (12)	0.09693 (16)	0.6207 (6)	0.0440 (6)
C4	0.34648 (14)	0.01067 (17)	0.6375 (6)	0.0529 (7)
H4	0.3137	−0.0131	0.5247	0.063*
C5	0.37617 (16)	−0.03939 (19)	0.8262 (7)	0.0627 (9)
H5	0.3632	−0.0975	0.8415	0.075*
C6	0.42479 (16)	−0.0037 (2)	0.9915 (7)	0.0666 (9)
H6	0.4435	−0.0385	1.1182	0.080*
C7	0.44684 (14)	0.0822 (2)	0.9761 (6)	0.0596 (8)
H7	0.4802	0.1054	1.0876	0.072*
C8	0.41680 (12)	0.13180 (17)	0.7871 (7)	0.0483 (6)
C9	0.23686 (13)	0.22885 (16)	−0.0549 (6)	0.0463 (7)
C10	0.16580 (12)	0.11539 (16)	−0.2849 (5)	0.0448 (7)
C11	0.12759 (13)	0.16537 (16)	−0.4543 (6)	0.0475 (7)
H11	0.1294	0.2257	−0.4476	0.057*
C12	0.08673 (13)	0.12370 (18)	−0.6333 (6)	0.0467 (7)
C13	0.08131 (14)	0.03494 (18)	−0.6548 (7)	0.0594 (9)
H13	0.0538	0.0090	−0.7799	0.071*
C14	0.11867 (17)	−0.01353 (19)	−0.4821 (8)	0.0669 (10)
H14	0.1158	−0.0738	−0.4884	0.080*
C15	0.16025 (13)	0.02508 (17)	−0.3002 (7)	0.0564 (8)
H15	0.1850	−0.0094	−0.1859	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.0952 (5)	0.0440 (4)	0.0682 (6)	0.0028 (4)	−0.0217 (6)	0.0061 (4)
O1	0.0843 (14)	0.0538 (12)	0.0697 (17)	−0.0173 (10)	−0.0095 (13)	0.0108 (11)
O2	0.1169 (18)	0.0549 (14)	0.124 (3)	−0.0056 (12)	−0.060 (2)	0.0259 (15)
O3	0.0610 (12)	0.0922 (16)	0.0540 (15)	0.0020 (11)	−0.0169 (12)	0.0025 (12)
N1	0.0572 (13)	0.0627 (15)	0.055 (2)	−0.0116 (10)	−0.0129 (13)	−0.0018 (13)
N2	0.0479 (11)	0.0467 (13)	0.0439 (15)	0.0030 (8)	−0.0014 (13)	−0.0011 (13)
N3	0.0608 (14)	0.0423 (13)	0.0501 (17)	−0.0004 (9)	−0.0107 (13)	0.0009 (11)
N4	0.0552 (12)	0.0424 (12)	0.0478 (16)	0.0017 (10)	−0.0072 (11)	0.0080 (10)
N5	0.0487 (12)	0.0632 (17)	0.060 (2)	−0.0013 (11)	−0.0065 (13)	0.0151 (14)
C1	0.0522 (15)	0.0573 (18)	0.048 (2)	−0.0067 (13)	0.0022 (15)	−0.0028 (15)
C2	0.0422 (13)	0.0482 (16)	0.0425 (18)	−0.0008 (10)	−0.0003 (13)	−0.0025 (12)
C3	0.0435 (13)	0.0491 (16)	0.0396 (18)	0.0049 (11)	0.0015 (13)	−0.0005 (13)
C4	0.0522 (15)	0.0536 (18)	0.053 (2)	0.0024 (12)	0.0011 (14)	0.0009 (14)
C5	0.0688 (17)	0.0548 (17)	0.064 (3)	0.0099 (13)	0.0049 (19)	0.0084 (16)
C6	0.0682 (19)	0.079 (2)	0.053 (2)	0.0252 (16)	0.0012 (17)	0.0140 (17)
C7	0.0555 (16)	0.080 (2)	0.043 (2)	0.0080 (15)	−0.0047 (15)	−0.0012 (15)
C8	0.0467 (12)	0.0569 (17)	0.0414 (18)	0.0025 (11)	0.0002 (16)	−0.0004 (15)
C9	0.0505 (13)	0.0425 (15)	0.0458 (19)	0.0059 (12)	0.0039 (15)	−0.0024 (13)
C10	0.0415 (12)	0.0475 (16)	0.045 (2)	0.0023 (10)	0.0007 (12)	0.0028 (12)
C11	0.0471 (14)	0.0470 (15)	0.0482 (19)	0.0040 (11)	−0.0006 (13)	0.0067 (13)
C12	0.0391 (11)	0.0543 (16)	0.047 (2)	0.0007 (12)	−0.0016 (12)	0.0111 (13)
C13	0.0543 (15)	0.0562 (18)	0.068 (3)	−0.0087 (13)	−0.0116 (17)	0.0010 (15)
C14	0.0692 (18)	0.0454 (16)	0.086 (3)	−0.0022 (14)	−0.0198 (19)	0.0051 (17)
C15	0.0495 (14)	0.0459 (16)	0.074 (2)	−0.0006 (12)	−0.0134 (16)	0.0120 (14)

S1—C9	1.655 (3)	C4—C5	1.382 (4)
O1—C1	1.223 (3)	C4—H4	0.9300
O2—N5	1.216 (3)	C5—C6	1.376 (5)
O3—N5	1.225 (3)	C5—H5	0.9300
N1—C1	1.365 (4)	C6—C7	1.386 (4)
N1—C8	1.402 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.382 (4)
N2—C2	1.282 (4)	C7—H7	0.9300
N2—N3	1.355 (3)	C10—C11	1.382 (4)
N3—C9	1.362 (4)	C10—C15	1.396 (3)
N3—H3	0.8600	C11—C12	1.378 (4)
N4—C9	1.346 (3)	C11—H11	0.9300
N4—C10	1.407 (3)	C12—C13	1.374 (4)
N4—H4A	0.8600	C13—C14	1.373 (4)
N5—C12	1.472 (4)	C13—H13	0.9300
C1—C2	1.513 (4)	C14—C15	1.375 (4)
C2—C3	1.448 (4)	C14—H14	0.9300
C3—C4	1.382 (3)	C15—H15	0.9300
C3—C8	1.393 (4)
C1—N1—C8	111.6 (2)	C5—C6—H6	118.8
C1—N1—H1	124.2	C7—C6—H6	118.8
C8—N1—H1	124.2	C8—C7—C6	116.8 (3)
C2—N2—N3	117.8 (2)	C8—C7—H7	121.6
N2—N3—C9	120.9 (2)	C6—C7—H7	121.6
N2—N3—H3	119.5	C7—C8—C3	121.4 (2)
C9—N3—H3	119.5	C7—C8—N1	128.9 (3)
C9—N4—C10	131.3 (2)	C3—C8—N1	109.7 (3)
C9—N4—H4A	114.3	N4—C9—N3	112.7 (2)
C10—N4—H4A	114.3	N4—C9—S1	128.8 (2)
O2—N5—O3	122.7 (3)	N3—C9—S1	118.5 (2)
O2—N5—C12	118.7 (3)	C11—C10—C15	118.5 (3)
O3—N5—C12	118.6 (2)	C11—C10—N4	124.9 (2)
O1—C1—N1	127.7 (3)	C15—C10—N4	116.6 (2)
O1—C1—C2	127.2 (3)	C12—C11—C10	118.5 (2)
N1—C1—C2	105.2 (2)	C12—C11—H11	120.8
N2—C2—C3	125.3 (2)	C10—C11—H11	120.8
N2—C2—C1	128.1 (2)	C13—C12—C11	124.1 (3)
C3—C2—C1	106.6 (2)	C13—C12—N5	118.6 (3)
C4—C3—C8	120.6 (3)	C11—C12—N5	117.3 (2)
C4—C3—C2	132.5 (3)	C14—C13—C12	116.5 (3)
C8—C3—C2	106.9 (2)	C14—C13—H13	121.7
C3—C4—C5	118.3 (3)	C12—C13—H13	121.7
C3—C4—H4	120.8	C13—C14—C15	121.5 (3)
C5—C4—H4	120.8	C13—C14—H14	119.2
C6—C5—C4	120.4 (3)	C15—C14—H14	119.2
C6—C5—H5	119.8	C14—C15—C10	120.8 (3)
C4—C5—H5	119.8	C14—C15—H15	119.6
C5—C6—C7	122.4 (3)	C10—C15—H15	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.21	3.058 (3)	170
N3—H3···O1	0.86	2.13	2.797 (3)	134
N4—H4A···N2	0.86	2.12	2.580 (3)	113
C7—H7···O2i	0.93	2.55	3.358 (4)	145
C11—H11···S1	0.93	2.56	3.204 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.21	3.058 (3)	170
N3—H3⋯O1	0.86	2.13	2.797 (3)	134
N4—H4A⋯N2	0.86	2.12	2.580 (3)	113
C7—H7⋯O2i	0.93	2.55	3.358 (4)	145
C11—H11⋯S1	0.93	2.56	3.204 (3)	127

Symmetry code: (i) .