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

In the title compound, C(16)H(14)N(4)O(2)S, intra-molecular N-H⋯N hydrogen bonding forms an S(5) ring, whereas N-H⋯O and C-H⋯S inter-actions complete S(6) ring motifs. In the crystal, mol-ecules form inversion dimers due to N-H⋯O inter-actions. The dimers are inter-linked through N-H⋯S hydrogen bonds and π-π inter-actions occur with a centroid-centroid distance of 3.8422 (11) Å between the meth-oxy-containing benzene ring and the five-membered heterocyclic ring.

Related literature

For the preparation and structures of biologically important N 4-aryl-substituted isatin-3-thio­semicarbazones, see: Pervez et al. (2007 ▶, 2008 ▶, 2009 ▶, 2010a ▶). For a related structure, see: Pervez et al. (2010b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14N4O2S

M = 326.37

Monoclinic,

a = 15.1793 (5) Å

b = 7.2473 (2) Å

c = 15.4764 (5) Å

β = 111.179 (2)°

V = 1587.55 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.34 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.946, T max = 0.960

13861 measured reflections

3925 independent reflections

2898 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.04

3925 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.35 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/S1600536810018052/si2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018052/si2262Isup2.hkl

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

C16H14N4O2S	F(000) = 680
Mr = 326.37	Dx = 1.366 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2898 reflections
a = 15.1793 (5) Å	θ = 3.2–28.3°
b = 7.2473 (2) Å	µ = 0.22 mm−1
c = 15.4764 (5) Å	T = 296 K
β = 111.179 (2)°	Prism, yellow
V = 1587.55 (9) Å3	0.34 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3925 independent reflections
Radiation source: fine-focus sealed tube	2898 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 3.2°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.946, Tmax = 0.960	l = −20→19
13861 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.6227P] where P = (Fo2 + 2Fc2)/3
3925 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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
C1	0.19826 (11)	0.3610 (2)	0.45348 (11)	0.0329 (3)
C2	0.26044 (11)	0.3126 (2)	0.54720 (11)	0.0345 (3)
C3	0.35347 (12)	0.2547 (3)	0.58412 (12)	0.0434 (4)
H3	0.3882	0.2332	0.5464	0.052*
C4	0.39313 (14)	0.2298 (3)	0.67919 (13)	0.0515 (5)
H4	0.4555	0.1908	0.7057	0.062*
C5	0.34181 (15)	0.2617 (3)	0.73516 (13)	0.0529 (5)
H5	0.3705	0.2446	0.7988	0.063*
C6	0.24859 (14)	0.3187 (3)	0.69884 (12)	0.0491 (5)
H6	0.2140	0.3403	0.7367	0.059*
C7	0.20928 (11)	0.3419 (2)	0.60448 (11)	0.0382 (4)
C8	0.10524 (11)	0.4125 (2)	0.46058 (11)	0.0359 (4)
C9	0.17432 (11)	0.4498 (2)	0.22293 (11)	0.0360 (4)
C10	0.30202 (12)	0.3962 (2)	0.16100 (12)	0.0388 (4)
C11	0.24941 (12)	0.3445 (2)	0.07119 (12)	0.0407 (4)
H11	0.1865	0.3103	0.0552	0.049*
C12	0.29128 (13)	0.3440 (3)	0.00497 (13)	0.0446 (4)
C13	0.38568 (14)	0.3931 (3)	0.02993 (15)	0.0539 (5)
H13	0.4139	0.3948	−0.0143	0.065*
C14	0.43705 (14)	0.4392 (3)	0.11998 (16)	0.0554 (5)
H14	0.5006	0.4689	0.1366	0.066*
C15	0.39605 (13)	0.4423 (3)	0.18678 (14)	0.0477 (4)
H15	0.4313	0.4748	0.2476	0.057*
C16	0.14733 (15)	0.2526 (3)	−0.11290 (15)	0.0613 (6)
H16A	0.1142	0.3578	−0.1023	0.092*
H16B	0.1387	0.1496	−0.0777	0.092*
H16C	0.1230	0.2222	−0.1776	0.092*
N1	0.11680 (10)	0.3984 (2)	0.55058 (10)	0.0429 (4)
H1	0.0733	0.4210	0.5725	0.051*
N2	0.22156 (9)	0.36975 (19)	0.38155 (9)	0.0351 (3)
N3	0.15482 (9)	0.4293 (2)	0.30214 (9)	0.0374 (3)
H3A	0.0992	0.4548	0.3013	0.045*
N4	0.26118 (10)	0.3955 (2)	0.23067 (10)	0.0416 (4)
H4A	0.2966	0.3552	0.2842	0.050*
O1	0.03312 (8)	0.45962 (19)	0.39631 (8)	0.0452 (3)
O2	0.24526 (10)	0.2944 (2)	−0.08484 (9)	0.0610 (4)
S1	0.09025 (3)	0.53985 (8)	0.13109 (3)	0.04856 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0311 (7)	0.0360 (8)	0.0318 (8)	0.0010 (6)	0.0115 (6)	−0.0041 (6)
C2	0.0357 (8)	0.0370 (9)	0.0304 (8)	0.0024 (6)	0.0115 (6)	−0.0028 (6)
C3	0.0409 (9)	0.0480 (10)	0.0403 (9)	0.0111 (7)	0.0136 (7)	−0.0015 (8)
C4	0.0456 (10)	0.0572 (12)	0.0423 (10)	0.0146 (9)	0.0045 (8)	0.0006 (9)
C5	0.0585 (12)	0.0603 (12)	0.0312 (9)	0.0100 (9)	0.0060 (8)	0.0039 (8)
C6	0.0547 (11)	0.0628 (12)	0.0320 (9)	0.0061 (9)	0.0182 (8)	−0.0004 (8)
C7	0.0370 (8)	0.0444 (9)	0.0329 (8)	0.0019 (7)	0.0123 (7)	−0.0013 (7)
C8	0.0306 (7)	0.0442 (9)	0.0335 (8)	−0.0012 (6)	0.0121 (6)	−0.0050 (7)
C9	0.0361 (8)	0.0396 (9)	0.0331 (8)	−0.0034 (7)	0.0136 (7)	−0.0010 (7)
C10	0.0408 (9)	0.0398 (9)	0.0411 (9)	0.0054 (7)	0.0211 (7)	0.0075 (7)
C11	0.0412 (9)	0.0431 (10)	0.0421 (9)	0.0028 (7)	0.0200 (7)	0.0032 (7)
C12	0.0518 (10)	0.0442 (10)	0.0445 (10)	0.0062 (8)	0.0253 (8)	0.0032 (8)
C13	0.0548 (11)	0.0636 (13)	0.0570 (12)	0.0033 (10)	0.0367 (10)	0.0059 (10)
C14	0.0414 (10)	0.0658 (13)	0.0656 (13)	−0.0035 (9)	0.0272 (10)	0.0046 (10)
C15	0.0415 (9)	0.0565 (12)	0.0465 (10)	0.0005 (8)	0.0174 (8)	0.0036 (9)
C16	0.0634 (13)	0.0705 (15)	0.0487 (12)	−0.0020 (11)	0.0187 (10)	−0.0053 (10)
N1	0.0337 (7)	0.0646 (10)	0.0332 (7)	0.0050 (7)	0.0154 (6)	−0.0018 (7)
N2	0.0345 (7)	0.0396 (8)	0.0317 (7)	0.0018 (6)	0.0124 (6)	−0.0014 (6)
N3	0.0303 (6)	0.0520 (9)	0.0304 (7)	0.0027 (6)	0.0114 (5)	0.0015 (6)
N4	0.0355 (7)	0.0579 (10)	0.0330 (7)	0.0072 (6)	0.0143 (6)	0.0079 (6)
O1	0.0303 (6)	0.0680 (9)	0.0342 (6)	0.0061 (5)	0.0081 (5)	−0.0031 (6)
O2	0.0614 (9)	0.0838 (11)	0.0445 (8)	0.0019 (8)	0.0272 (7)	−0.0089 (7)
S1	0.0377 (2)	0.0708 (4)	0.0363 (2)	0.0074 (2)	0.01228 (18)	0.0104 (2)

C1—N2	1.286 (2)	C10—C11	1.381 (2)
C1—C2	1.459 (2)	C10—N4	1.425 (2)
C1—C8	1.503 (2)	C11—C12	1.387 (2)
C2—C3	1.383 (2)	C11—H11	0.9300
C2—C7	1.390 (2)	C12—O2	1.359 (2)
C3—C4	1.386 (3)	C12—C13	1.389 (3)
C3—H3	0.9300	C13—C14	1.370 (3)
C4—C5	1.378 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.386 (3)
C5—C6	1.384 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.374 (2)	C16—O2	1.422 (3)
C6—H6	0.9300	C16—H16A	0.9600
C7—N1	1.410 (2)	C16—H16B	0.9600
C8—O1	1.2319 (19)	C16—H16C	0.9600
C8—N1	1.343 (2)	N1—H1	0.8600
C9—N4	1.339 (2)	N2—N3	1.3504 (18)
C9—N3	1.369 (2)	N3—H3A	0.8600
C9—S1	1.6624 (17)	N4—H4A	0.8600
C10—C15	1.377 (2)
N2—C1—C2	126.25 (14)	C10—C11—H11	120.3
N2—C1—C8	127.64 (14)	C12—C11—H11	120.3
C2—C1—C8	105.94 (13)	O2—C12—C11	123.55 (17)
C3—C2—C7	120.33 (15)	O2—C12—C13	116.72 (17)
C3—C2—C1	132.91 (15)	C11—C12—C13	119.72 (18)
C7—C2—C1	106.72 (13)	C14—C13—C12	119.75 (18)
C2—C3—C4	117.73 (17)	C14—C13—H13	120.1
C2—C3—H3	121.1	C12—C13—H13	120.1
C4—C3—H3	121.1	C13—C14—C15	121.26 (18)
C5—C4—C3	121.22 (17)	C13—C14—H14	119.4
C5—C4—H4	119.4	C15—C14—H14	119.4
C3—C4—H4	119.4	C10—C15—C14	118.52 (18)
C4—C5—C6	121.48 (17)	C10—C15—H15	120.7
C4—C5—H5	119.3	C14—C15—H15	120.7
C6—C5—H5	119.3	O2—C16—H16A	109.5
C7—C6—C5	117.13 (17)	O2—C16—H16B	109.5
C7—C6—H6	121.4	H16A—C16—H16B	109.5
C5—C6—H6	121.4	O2—C16—H16C	109.5
C6—C7—C2	122.09 (16)	H16A—C16—H16C	109.5
C6—C7—N1	128.44 (16)	H16B—C16—H16C	109.5
C2—C7—N1	109.47 (14)	C8—N1—C7	111.39 (14)
O1—C8—N1	127.11 (15)	C8—N1—H1	124.3
O1—C8—C1	126.47 (15)	C7—N1—H1	124.3
N1—C8—C1	106.42 (13)	C1—N2—N3	116.95 (13)
N4—C9—N3	114.35 (14)	N2—N3—C9	121.05 (13)
N4—C9—S1	128.21 (13)	N2—N3—H3A	119.5
N3—C9—S1	117.43 (12)	C9—N3—H3A	119.5
C15—C10—C11	121.28 (16)	C9—N4—C10	127.93 (14)
C15—C10—N4	118.06 (16)	C9—N4—H4A	116.0
C11—C10—N4	120.61 (15)	C10—N4—H4A	116.0
C10—C11—C12	119.44 (16)	C12—O2—C16	117.57 (15)
N2—C1—C2—C3	−4.6 (3)	C10—C11—C12—C13	0.8 (3)
C8—C1—C2—C3	179.95 (19)	O2—C12—C13—C14	−178.02 (19)
N2—C1—C2—C7	172.98 (16)	C11—C12—C13—C14	0.9 (3)
C8—C1—C2—C7	−2.51 (18)	C12—C13—C14—C15	−1.6 (3)
C7—C2—C3—C4	−0.8 (3)	C11—C10—C15—C14	1.2 (3)
C1—C2—C3—C4	176.49 (19)	N4—C10—C15—C14	178.50 (17)
C2—C3—C4—C5	0.0 (3)	C13—C14—C15—C10	0.6 (3)
C3—C4—C5—C6	0.4 (3)	O1—C8—N1—C7	−179.55 (17)
C4—C5—C6—C7	0.1 (3)	C1—C8—N1—C7	0.0 (2)
C5—C6—C7—C2	−0.9 (3)	C6—C7—N1—C8	177.47 (19)
C5—C6—C7—N1	−179.92 (19)	C2—C7—N1—C8	−1.6 (2)
C3—C2—C7—C6	1.3 (3)	C2—C1—N2—N3	−175.68 (15)
C1—C2—C7—C6	−176.60 (17)	C8—C1—N2—N3	−1.2 (2)
C3—C2—C7—N1	−179.52 (16)	C1—N2—N3—C9	177.49 (15)
C1—C2—C7—N1	2.6 (2)	N4—C9—N3—N2	3.9 (2)
N2—C1—C8—O1	5.7 (3)	S1—C9—N3—N2	−175.20 (12)
C2—C1—C8—O1	−178.91 (17)	N3—C9—N4—C10	178.85 (16)
N2—C1—C8—N1	−173.84 (17)	S1—C9—N4—C10	−2.1 (3)
C2—C1—C8—N1	1.57 (19)	C15—C10—N4—C9	142.08 (19)
C15—C10—C11—C12	−1.8 (3)	C11—C10—N4—C9	−40.6 (3)
N4—C10—C11—C12	−179.12 (16)	C11—C12—O2—C16	4.2 (3)
C10—C11—C12—O2	179.65 (17)	C13—C12—O2—C16	−176.89 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.04	2.875 (2)	164
N3—H3A···O1	0.86	2.06	2.7441 (19)	136
N4—H4A···N2	0.86	2.19	2.620 (2)	110
N4—H4A···S1ii	0.86	2.87	3.5806 (16)	141
C11—H11···S1	0.93	2.74	3.212 (2)	112
C8—O1···Cg3iii	1.2319 (19)	3.6366 (1)	3.7399 (17)	85.16 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.04	2.875 (2)	164
N3—H3A⋯O1	0.86	2.06	2.7441 (19)	136
N4—H4A⋯N2	0.86	2.19	2.620 (2)	110
N4—H4A⋯S1ii	0.86	2.87	3.5806 (16)	141
C11—H11⋯S1	0.93	2.74	3.212 (2)	112

Symmetry codes: (i) ; (ii) .