(3Z)-3-Hydrazinylideneindolin-2-one.

The title mol-ecule, C(8)H(7)N(3)O, is almost planar, with a maximum deviation of 0.0232 (2) Å from the least-squares plane. The Z conformation of the C=N double bond is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, adjacent mol-ecules are linked by inter-molecular N-H⋯N and N-H⋯O hydrogen bonds, forming zigzag sheets parallel to the c axis; the sheets are further stabilized by π-π inter-actions [centroid-centroid distance = 3.7390 (10) Å].

Related literature

For the biological activity of related compounds, see: Sarangapani et al. (1994 ▶). For related structures, see: Ali et al. (2005a ▶,b ▶); Pelosi et al. (2005 ▶).

Experimental

Crystal data

C8H7N3O

M = 161.17

Orthorhombic,

a = 4.7211 (5) Å

b = 11.4263 (13) Å

c = 13.3693 (15) Å

V = 721.20 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.50 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.950, T max = 0.991

4234 measured reflections

811 independent reflections

776 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.08

811 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035367/ng5222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035367/ng5222Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035367/ng5222Isup3.cml

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

C8H7N3O	Dx = 1.484 Mg m−3
Mr = 161.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2104 reflections
a = 4.7211 (5) Å	θ = 3.1–27.5°
b = 11.4263 (13) Å	µ = 0.10 mm−1
c = 13.3693 (15) Å	T = 273 K
V = 721.20 (14) Å3	Plate, colorles
Z = 4	0.50 × 0.10 × 0.09 mm
F(000) = 336

Bruker SMART APEX CCD area-detector diffractometer	811 independent reflections
Radiation source: fine-focus sealed tube	776 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→5
Tmin = 0.950, Tmax = 0.991	k = −13→13
4234 measured reflections	l = −16→15

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0832P] where P = (Fo2 + 2Fc2)/3
811 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.1159 (3)	0.11147 (11)	0.46693 (10)	0.0443 (4)
N2	0.2067 (3)	−0.13322 (13)	0.54465 (10)	0.0345 (4)
N3	0.0172 (4)	−0.12868 (16)	0.47156 (13)	0.0429 (4)
C8	0.5392 (4)	−0.02667 (15)	0.65275 (13)	0.0331 (4)
C6	0.2809 (4)	0.08289 (15)	0.53444 (14)	0.0343 (4)
C7	0.3271 (4)	−0.03705 (14)	0.57432 (13)	0.0317 (4)
N1	0.4577 (4)	0.15444 (13)	0.58597 (13)	0.0405 (4)
C1	0.6635 (5)	−0.10479 (17)	0.71866 (14)	0.0408 (5)
H1A	0.6159	−0.1837	0.7167	0.049*
C4	0.8090 (5)	0.13277 (19)	0.72546 (15)	0.0460 (5)
H4A	0.8570	0.2117	0.7277	0.055*
C2	0.8591 (5)	−0.06419 (19)	0.78751 (15)	0.0469 (5)
H2B	0.9425	−0.1160	0.8323	0.056*
C5	0.6139 (4)	0.09186 (16)	0.65757 (14)	0.0357 (5)
C3	0.9315 (5)	0.0535 (2)	0.79003 (16)	0.0491 (6)
H3A	1.0651	0.0794	0.8361	0.059*
H2N3	−0.028 (5)	−0.060 (2)	0.4466 (16)	0.048 (6)*
H1N3	−0.064 (6)	−0.199 (2)	0.4587 (17)	0.066 (8)*
H1N1	0.481 (6)	0.231 (2)	0.5712 (16)	0.060 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0552 (9)	0.0305 (7)	0.0471 (7)	0.0065 (6)	−0.0067 (7)	0.0062 (6)
N2	0.0372 (8)	0.0285 (8)	0.0379 (8)	−0.0002 (7)	0.0034 (7)	0.0003 (6)
N3	0.0488 (10)	0.0313 (9)	0.0485 (9)	−0.0036 (8)	−0.0060 (9)	0.0006 (8)
C8	0.0338 (10)	0.0300 (9)	0.0356 (9)	0.0003 (9)	0.0061 (8)	0.0005 (7)
C6	0.0382 (10)	0.0273 (9)	0.0374 (9)	0.0020 (8)	0.0044 (9)	0.0014 (7)
C7	0.0342 (9)	0.0237 (8)	0.0371 (8)	0.0007 (8)	0.0047 (8)	0.0004 (7)
N1	0.0488 (10)	0.0234 (8)	0.0494 (9)	−0.0043 (7)	0.0025 (9)	0.0039 (7)
C1	0.0448 (11)	0.0346 (10)	0.0430 (10)	0.0047 (10)	0.0000 (10)	0.0022 (8)
C4	0.0437 (12)	0.0425 (11)	0.0517 (11)	−0.0096 (11)	0.0048 (10)	−0.0088 (9)
C2	0.0454 (12)	0.0545 (12)	0.0407 (10)	0.0126 (11)	−0.0036 (10)	−0.0016 (9)
C5	0.0365 (11)	0.0313 (9)	0.0393 (9)	−0.0031 (8)	0.0062 (8)	−0.0005 (7)
C3	0.0402 (12)	0.0627 (14)	0.0443 (10)	0.0001 (11)	−0.0030 (10)	−0.0113 (10)

O1—C6	1.236 (2)	N1—C5	1.404 (3)
N2—C7	1.299 (2)	N1—H1N1	0.90 (2)
N2—N3	1.326 (2)	C1—C2	1.384 (3)
N3—H2N3	0.88 (2)	C1—H1A	0.9300
N3—H1N3	0.91 (3)	C4—C5	1.375 (3)
C8—C1	1.385 (3)	C4—C3	1.378 (3)
C8—C5	1.401 (3)	C4—H4A	0.9300
C8—C7	1.455 (3)	C2—C3	1.388 (3)
C6—N1	1.356 (3)	C2—H2B	0.9300
C6—C7	1.487 (2)	C3—H3A	0.9300
C7—N2—N3	119.15 (15)	C2—C1—C8	119.33 (19)
N2—N3—H2N3	118.5 (15)	C2—C1—H1A	120.3
N2—N3—H1N3	112.9 (15)	C8—C1—H1A	120.3
H2N3—N3—H1N3	128 (2)	C5—C4—C3	118.1 (2)
C1—C8—C5	119.17 (19)	C5—C4—H4A	120.9
C1—C8—C7	134.24 (18)	C3—C4—H4A	120.9
C5—C8—C7	106.57 (15)	C1—C2—C3	120.3 (2)
O1—C6—N1	126.82 (17)	C1—C2—H2B	119.8
O1—C6—C7	126.73 (17)	C3—C2—H2B	119.8
N1—C6—C7	106.45 (16)	C4—C5—C8	121.84 (18)
N2—C7—C8	126.17 (16)	C4—C5—N1	128.95 (18)
N2—C7—C6	127.29 (17)	C8—C5—N1	109.21 (17)
C8—C7—C6	106.52 (15)	C4—C3—C2	121.2 (2)
C6—N1—C5	111.25 (15)	C4—C3—H3A	119.4
C6—N1—H1N1	123.2 (16)	C2—C3—H3A	119.4
C5—N1—H1N1	125.3 (17)
N3—N2—C7—C8	−179.67 (18)	C7—C8—C1—C2	−178.4 (2)
N3—N2—C7—C6	−0.8 (3)	C8—C1—C2—C3	−0.4 (3)
C1—C8—C7—N2	−3.2 (4)	C3—C4—C5—C8	−0.2 (3)
C5—C8—C7—N2	178.52 (18)	C3—C4—C5—N1	178.8 (2)
C1—C8—C7—C6	177.8 (2)	C1—C8—C5—C4	0.6 (3)
C5—C8—C7—C6	−0.5 (2)	C7—C8—C5—C4	179.15 (17)
O1—C6—C7—N2	1.1 (3)	C1—C8—C5—N1	−178.57 (17)
N1—C6—C7—N2	−178.18 (18)	C7—C8—C5—N1	0.0 (2)
O1—C6—C7—C8	−179.83 (17)	C6—N1—C5—C4	−178.5 (2)
N1—C6—C7—C8	0.8 (2)	C6—N1—C5—C8	0.6 (2)
O1—C6—N1—C5	179.82 (17)	C5—C4—C3—C2	−0.5 (3)
C7—C6—N1—C5	−0.9 (2)	C1—C2—C3—C4	0.8 (3)
C5—C8—C1—C2	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N3···O1	0.88 (2)	2.09 (2)	2.784 (2)	135 (2)
N3—H1N3···N2i	0.91 (2)	2.20 (3)	3.098 (2)	169 (2)
N1—H1N1···O1ii	0.90 (2)	1.98 (2)	2.866 (2)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H2N3⋯O1	0.88 (2)	2.09 (2)	2.784 (2)	135 (2)
N3—H1N3⋯N2i	0.91 (2)	2.20 (3)	3.098 (2)	169 (2)
N1—H1N1⋯O1ii	0.90 (2)	1.98 (2)	2.866 (2)	168 (3)

Symmetry codes: (i) ; (ii) .