(3Z)-3-[(Z)-2-(2-Oxoindolin-3-yl-idene)hydrazin-1-yl-idene]indolin-2-one 0.17-hydrate.

In the title compound, C16H10N4O2·0.17H2O, prepared by the one-step condensation reaction of isatin with hydrazine hydrate under microwave irradiation, the complete organic mol-ecule is generated by crystallographic inversion symmetry and therefore exists in an S-trans conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating a three-dimensional framework with [001] channels, which are occupied by the disordered water mol-ecules.

Related literature

For background to microwave synthesis, see: Hoz et al. (2004 ▶); Jagani et al. (2012 ▶). For our previous work in this area, see: Liu et al. (2008 ▶); Wang et al. (2010 ▶). For the coventional synthesis of the title compound, see: Ali & Alam (1994 ▶).

Experimental

Crystal data

C16H10N4O2·0.17H2O

M = 308.30

Trigonal,

a = 24.8699 (18) Å

c = 5.6603 (8) Å

V = 3031.9 (5) Å3

Z = 9

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.38 × 0.16 × 0.14 mm

Data collection

Bruker SMART1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.963, T max = 0.986

8691 measured reflections

1547 independent reflections

1290 reflections with I > 2σigma(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.01

1547 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814011805/hb7227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011805/hb7227Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011805/hb7227Isup3.cml

CCDC reference: 1004532

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H10N4O2·0.17H2O	F(000) = 1369
Mr = 308.30	Dx = 1.450 Mg m−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	θ = 2.8–27.2°
a = 24.8699 (18) Å	µ = 0.10 mm−1
c = 5.6603 (8) Å	T = 296 K
V = 3031.9 (5) Å3	Block, brown
Z = 9	0.38 × 0.16 × 0.14 mm

Bruker SMART1000 CCD diffractometer	1547 independent reflections
Radiation source: fine-focus sealed tube	1290 reflections with I > 2σigma(I)
Graphite monochromator	Rint = 0.025
thin–slice ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −32→32
Tmin = 0.963, Tmax = 0.986	k = −29→32
8691 measured reflections	l = −7→7

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0545P)2 + 2.5765P] where P = (Fo2 + 2Fc2)/3
1547 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. The title compound was synthesized under microwave irradiation.

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	Occ. (<1)
C1	0.25001 (6)	0.06795 (6)	0.2063 (2)	0.0345 (3)
C2	0.20279 (7)	0.05119 (7)	0.3672 (3)	0.0429 (3)
H2	0.1975	0.0250	0.4934	0.051*
C3	0.16336 (8)	0.07495 (8)	0.3331 (3)	0.0515 (4)
H3	0.1310	0.0644	0.4390	0.062*
C4	0.17099 (8)	0.11403 (8)	0.1452 (3)	0.0521 (4)
H4	0.1434	0.1286	0.1257	0.063*
C5	0.21929 (7)	0.13147 (7)	−0.0134 (3)	0.0439 (3)
H5	0.2247	0.1581	−0.1379	0.053*
C6	0.25943 (6)	0.10844 (6)	0.0170 (2)	0.0341 (3)
C7	0.31363 (6)	0.11575 (6)	−0.1095 (2)	0.0336 (3)
C8	0.33439 (6)	0.07495 (6)	0.0163 (2)	0.0349 (3)
N1	0.29469 (5)	0.04931 (5)	0.20131 (19)	0.0386 (3)
H1	0.2967	0.0246	0.3026	0.046*
N2	0.34522 (6)	0.14844 (5)	−0.2881 (2)	0.0406 (3)
O1	0.37735 (5)	0.06693 (5)	−0.03535 (18)	0.0459 (3)
O1W	0.0000	0.0000	0.248 (4)	0.177 (8)	0.25

	U11	U22	U33	U12	U13	U23
C1	0.0402 (7)	0.0309 (6)	0.0306 (6)	0.0163 (5)	0.0026 (5)	0.0005 (5)
C2	0.0495 (8)	0.0409 (7)	0.0372 (7)	0.0217 (6)	0.0112 (6)	0.0069 (6)
C3	0.0532 (9)	0.0532 (9)	0.0516 (9)	0.0291 (8)	0.0181 (7)	0.0037 (7)
C4	0.0582 (9)	0.0549 (9)	0.0574 (10)	0.0388 (8)	0.0097 (7)	0.0033 (7)
C5	0.0547 (9)	0.0410 (7)	0.0422 (8)	0.0287 (7)	0.0055 (6)	0.0060 (6)
C6	0.0412 (7)	0.0297 (6)	0.0297 (6)	0.0165 (5)	0.0034 (5)	0.0017 (5)
C7	0.0385 (7)	0.0309 (6)	0.0281 (6)	0.0149 (5)	0.0011 (5)	0.0005 (5)
C8	0.0394 (7)	0.0345 (6)	0.0292 (6)	0.0173 (5)	0.0018 (5)	0.0003 (5)
N1	0.0461 (6)	0.0415 (6)	0.0327 (6)	0.0252 (5)	0.0067 (5)	0.0103 (5)
N2	0.0460 (7)	0.0416 (6)	0.0335 (6)	0.0214 (5)	0.0066 (5)	0.0095 (5)
O1	0.0479 (6)	0.0568 (6)	0.0415 (6)	0.0325 (5)	0.0074 (4)	0.0050 (5)
O1W	0.093 (6)	0.093 (6)	0.34 (3)	0.047 (3)	0.000	0.000

C1—C2	1.3756 (19)	C5—C6	1.388 (2)
C1—N1	1.4022 (17)	C5—H5	0.9300
C1—C6	1.4073 (17)	C6—C7	1.4554 (18)
C2—C3	1.389 (2)	C7—N2	1.2891 (17)
C2—H2	0.9300	C7—C8	1.5254 (18)
C3—C4	1.388 (2)	C8—O1	1.2165 (17)
C3—H3	0.9300	C8—N1	1.3594 (17)
C4—C5	1.384 (2)	N1—H1	0.8593
C4—H4	0.9300	N2—N2i	1.404 (2)
C2—C1—N1	127.63 (12)	C6—C5—H5	120.6
C2—C1—C6	122.16 (13)	C5—C6—C1	119.53 (12)
N1—C1—C6	110.21 (11)	C5—C6—C7	134.43 (12)
C1—C2—C3	117.17 (13)	C1—C6—C7	106.04 (11)
C1—C2—H2	121.4	N2—C7—C6	134.34 (12)
C3—C2—H2	121.4	N2—C7—C8	118.92 (12)
C4—C3—C2	121.72 (14)	C6—C7—C8	106.71 (10)
C4—C3—H3	119.1	O1—C8—N1	126.85 (12)
C2—C3—H3	119.1	O1—C8—C7	127.86 (12)
C5—C4—C3	120.64 (14)	N1—C8—C7	105.29 (11)
C5—C4—H4	119.7	C8—N1—C1	111.72 (10)
C3—C4—H4	119.7	C8—N1—H1	124.1
C4—C5—C6	118.75 (13)	C1—N1—H1	124.2
C4—C5—H5	120.6	C7—N2—N2i	111.89 (14)
N1—C1—C2—C3	−178.92 (14)	C5—C6—C7—C8	−177.99 (15)
C6—C1—C2—C3	1.3 (2)	C1—C6—C7—C8	1.50 (14)
C1—C2—C3—C4	0.0 (2)	N2—C7—C8—O1	−2.8 (2)
C2—C3—C4—C5	−1.1 (3)	C6—C7—C8—O1	178.67 (13)
C3—C4—C5—C6	0.9 (2)	N2—C7—C8—N1	176.85 (12)
C4—C5—C6—C1	0.3 (2)	C6—C7—C8—N1	−1.65 (14)
C4—C5—C6—C7	179.71 (15)	O1—C8—N1—C1	−179.13 (13)
C2—C1—C6—C5	−1.4 (2)	C7—C8—N1—C1	1.18 (14)
N1—C1—C6—C5	178.74 (12)	C2—C1—N1—C8	179.94 (13)
C2—C1—C6—C7	178.98 (12)	C6—C1—N1—C8	−0.26 (15)
N1—C1—C6—C7	−0.83 (14)	C6—C7—N2—N2i	0.1 (2)
C5—C6—C7—N2	3.8 (3)	C8—C7—N2—N2i	−177.92 (13)
C1—C6—C7—N2	−176.67 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.86	2.13	2.8951 (17)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.13	2.8951 (17)	148

Symmetry code: (i) .