3-(2-Ethyl-2-phenyl-hydrazin-1-yl-idene)indolin-2-one.

In the title compound, C16H15N3O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The mol-ecular conformation is supported by an intra-molecular C-H⋯O inter-action, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R2(2)(8) loops.

Related literature

For a related structure, see: Jamal et al. (2011 ▶). For background to Schiff bases, see: Chaluvaraju & Zaranappa (2011 ▶); Khan et al. (2009 ▶).

Experimental

Crystal data

C16H15N3O

M = 265.31

Monoclinic,

a = 9.463 (2) Å

b = 17.303 (4) Å

c = 8.5403 (18) Å

β = 104.427 (5)°

V = 1354.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.35 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.971, T max = 0.995

7875 measured reflections

2448 independent reflections

1783 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 1.08

2448 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047988/hb6996sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047988/hb6996Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047988/hb6996Isup3.cml

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

C16H15N3O	F(000) = 560
Mr = 265.31	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.463 (2) Å	Cell parameters from 1614 reflections
b = 17.303 (4) Å	θ = 2.7–28.2°
c = 8.5403 (18) Å	µ = 0.08 mm−1
β = 104.427 (5)°	T = 273 K
V = 1354.3 (5) Å3	Plate, yellow
Z = 4	0.35 × 0.18 × 0.06 mm

Bruker SMART APEX CCD diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	1783 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.971, Tmax = 0.995	k = −20→20
7875 measured reflections	l = −10→10

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.2688P] where P = (Fo2 + 2Fc2)/3
2448 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 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	0.65674 (17)	0.05361 (9)	−0.36767 (16)	0.0663 (5)
N1	0.52529 (18)	−0.04875 (9)	−0.31253 (18)	0.0506 (5)
H1A	0.4712	−0.0548	−0.4088	0.061*
N2	0.79812 (16)	0.02839 (8)	0.01956 (17)	0.0389 (4)
N3	0.89404 (17)	0.08210 (9)	0.00675 (17)	0.0426 (4)
C1	0.5134 (2)	−0.09387 (10)	−0.1807 (2)	0.0419 (5)
C2	0.4213 (2)	−0.15483 (11)	−0.1754 (2)	0.0508 (5)
H2B	0.3551	−0.1723	−0.2682	0.061*
C3	0.4310 (2)	−0.18901 (12)	−0.0267 (3)	0.0547 (6)
H3A	0.3707	−0.2306	−0.0194	0.066*
C4	0.5286 (2)	−0.16256 (11)	0.1112 (2)	0.0515 (5)
H4A	0.5317	−0.1859	0.2101	0.062*
C5	0.6221 (2)	−0.10171 (11)	0.1042 (2)	0.0446 (5)
H5A	0.6884	−0.0844	0.1971	0.053*
C6	0.6148 (2)	−0.06736 (10)	−0.0437 (2)	0.0392 (4)
C7	0.6978 (2)	−0.00462 (10)	−0.0925 (2)	0.0397 (5)
C8	0.6314 (2)	0.00580 (11)	−0.2721 (2)	0.0473 (5)
C9	0.9830 (2)	0.10795 (10)	0.1577 (2)	0.0408 (5)
C10	1.0982 (2)	0.15798 (12)	0.1632 (2)	0.0526 (5)
H10A	1.1160	0.1764	0.0676	0.063*
C11	1.1871 (2)	0.18077 (13)	0.3106 (3)	0.0639 (6)
H11A	1.2647	0.2141	0.3128	0.077*
C12	1.1626 (3)	0.15511 (13)	0.4522 (3)	0.0685 (7)
H12A	1.2232	0.1703	0.5507	0.082*
C13	1.0470 (3)	0.10645 (13)	0.4474 (3)	0.0661 (7)
H13A	1.0295	0.0888	0.5437	0.079*
C14	0.9564 (2)	0.08325 (11)	0.3022 (2)	0.0524 (5)
H14A	0.8775	0.0510	0.3012	0.063*
C15	0.9259 (2)	0.10639 (11)	−0.1461 (2)	0.0485 (5)
H15A	0.8863	0.0684	−0.2289	0.058*
H15B	1.0308	0.1079	−0.1319	0.058*
C16	0.8632 (2)	0.18441 (12)	−0.2025 (3)	0.0636 (6)
H16A	0.8869	0.1974	−0.3022	0.095*
H16B	0.9037	0.2226	−0.1222	0.095*
H16C	0.7592	0.1831	−0.2190	0.095*

	U11	U22	U33	U12	U13	U23
O1	0.0818 (11)	0.0690 (10)	0.0388 (8)	−0.0259 (9)	−0.0025 (7)	0.0131 (7)
N1	0.0587 (11)	0.0518 (10)	0.0347 (8)	−0.0096 (9)	−0.0008 (7)	−0.0005 (7)
N2	0.0412 (9)	0.0364 (8)	0.0376 (8)	0.0002 (7)	0.0070 (7)	0.0019 (7)
N3	0.0475 (10)	0.0431 (9)	0.0362 (8)	−0.0058 (8)	0.0084 (7)	0.0035 (7)
C1	0.0452 (11)	0.0397 (10)	0.0392 (10)	0.0032 (9)	0.0075 (8)	−0.0009 (8)
C2	0.0502 (13)	0.0467 (12)	0.0536 (12)	−0.0066 (10)	0.0091 (10)	−0.0082 (10)
C3	0.0551 (13)	0.0460 (12)	0.0640 (14)	−0.0083 (10)	0.0167 (11)	0.0001 (10)
C4	0.0528 (13)	0.0500 (12)	0.0532 (12)	0.0005 (10)	0.0158 (10)	0.0110 (10)
C5	0.0427 (11)	0.0486 (11)	0.0405 (11)	0.0037 (9)	0.0068 (8)	0.0036 (9)
C6	0.0381 (10)	0.0375 (10)	0.0406 (10)	0.0039 (8)	0.0073 (8)	0.0005 (8)
C7	0.0434 (11)	0.0384 (10)	0.0354 (9)	0.0015 (9)	0.0063 (8)	0.0015 (8)
C8	0.0552 (13)	0.0466 (11)	0.0362 (10)	−0.0032 (10)	0.0040 (9)	0.0017 (9)
C9	0.0418 (11)	0.0359 (10)	0.0422 (10)	0.0025 (9)	0.0058 (8)	−0.0015 (8)
C10	0.0495 (12)	0.0522 (12)	0.0559 (13)	−0.0055 (10)	0.0124 (10)	−0.0013 (10)
C11	0.0513 (14)	0.0584 (14)	0.0742 (16)	−0.0082 (11)	0.0010 (11)	−0.0089 (12)
C12	0.0771 (17)	0.0580 (14)	0.0557 (14)	−0.0023 (13)	−0.0113 (12)	−0.0086 (11)
C13	0.0910 (18)	0.0603 (14)	0.0404 (12)	−0.0040 (14)	0.0042 (11)	−0.0006 (10)
C14	0.0635 (14)	0.0495 (12)	0.0422 (11)	−0.0071 (11)	0.0095 (10)	−0.0004 (9)
C15	0.0481 (12)	0.0550 (12)	0.0426 (11)	−0.0001 (10)	0.0119 (9)	0.0024 (9)
C16	0.0624 (15)	0.0605 (14)	0.0656 (14)	0.0000 (12)	0.0113 (11)	0.0163 (11)

O1—C8	1.227 (2)	C7—C8	1.517 (2)
N1—C8	1.359 (2)	C9—C10	1.384 (3)
N1—C1	1.398 (2)	C9—C14	1.387 (3)
N1—H1A	0.8600	C10—C11	1.386 (3)
N2—C7	1.300 (2)	C10—H10A	0.9300
N2—N3	1.323 (2)	C11—C12	1.361 (3)
N3—C9	1.425 (2)	C11—H11A	0.9300
N3—C15	1.472 (2)	C12—C13	1.373 (3)
C1—C2	1.376 (3)	C12—H12A	0.9300
C1—C6	1.393 (2)	C13—C14	1.380 (3)
C2—C3	1.383 (3)	C13—H13A	0.9300
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.381 (3)	C15—C16	1.504 (3)
C3—H3A	0.9300	C15—H15A	0.9700
C4—C5	1.386 (3)	C15—H15B	0.9700
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.382 (2)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.460 (3)
C8—N1—C1	112.74 (15)	C10—C9—C14	118.60 (18)
C8—N1—H1A	123.6	C10—C9—N3	120.67 (17)
C1—N1—H1A	123.6	C14—C9—N3	120.73 (17)
C7—N2—N3	129.64 (15)	C9—C10—C11	120.3 (2)
N2—N3—C9	114.13 (14)	C9—C10—H10A	119.9
N2—N3—C15	124.76 (15)	C11—C10—H10A	119.9
C9—N3—C15	120.49 (16)	C12—C11—C10	121.0 (2)
C2—C1—C6	122.30 (17)	C12—C11—H11A	119.5
C2—C1—N1	129.31 (17)	C10—C11—H11A	119.5
C6—C1—N1	108.40 (16)	C11—C12—C13	119.0 (2)
C1—C2—C3	117.40 (18)	C11—C12—H12A	120.5
C1—C2—H2B	121.3	C13—C12—H12A	120.5
C3—C2—H2B	121.3	C12—C13—C14	121.1 (2)
C4—C3—C2	121.2 (2)	C12—C13—H13A	119.4
C4—C3—H3A	119.4	C14—C13—H13A	119.4
C2—C3—H3A	119.4	C13—C14—C9	120.0 (2)
C3—C4—C5	120.91 (19)	C13—C14—H14A	120.0
C3—C4—H4A	119.5	C9—C14—H14A	120.0
C5—C4—H4A	119.5	N3—C15—C16	112.86 (17)
C6—C5—C4	118.62 (18)	N3—C15—H15A	109.0
C6—C5—H5A	120.7	C16—C15—H15A	109.0
C4—C5—H5A	120.7	N3—C15—H15B	109.0
C5—C6—C1	119.53 (18)	C16—C15—H15B	109.0
C5—C6—C7	132.28 (16)	H15A—C15—H15B	107.8
C1—C6—C7	108.18 (15)	C15—C16—H16A	109.5
N2—C7—C6	117.53 (15)	C15—C16—H16B	109.5
N2—C7—C8	137.30 (17)	H16A—C16—H16B	109.5
C6—C7—C8	105.09 (15)	C15—C16—H16C	109.5
O1—C8—N1	123.66 (17)	H16A—C16—H16C	109.5
O1—C8—C7	130.73 (18)	H16B—C16—H16C	109.5
N1—C8—C7	105.54 (16)
C7—N2—N3—C9	176.71 (17)	C1—N1—C8—O1	−177.0 (2)
C7—N2—N3—C15	−12.3 (3)	C1—N1—C8—C7	0.2 (2)
C8—N1—C1—C2	−178.8 (2)	N2—C7—C8—O1	−1.0 (4)
C8—N1—C1—C6	1.2 (2)	C6—C7—C8—O1	175.5 (2)
C6—C1—C2—C3	0.9 (3)	N2—C7—C8—N1	−178.0 (2)
N1—C1—C2—C3	−179.08 (19)	C6—C7—C8—N1	−1.4 (2)
C1—C2—C3—C4	0.5 (3)	N2—N3—C9—C10	173.23 (16)
C2—C3—C4—C5	−1.3 (3)	C15—N3—C9—C10	1.8 (3)
C3—C4—C5—C6	0.6 (3)	N2—N3—C9—C14	−6.5 (3)
C4—C5—C6—C1	0.7 (3)	C15—N3—C9—C14	−177.88 (17)
C4—C5—C6—C7	−178.50 (19)	C14—C9—C10—C11	1.9 (3)
C2—C1—C6—C5	−1.6 (3)	N3—C9—C10—C11	−177.84 (18)
N1—C1—C6—C5	178.46 (17)	C9—C10—C11—C12	−0.5 (3)
C2—C1—C6—C7	177.86 (17)	C10—C11—C12—C13	−0.5 (4)
N1—C1—C6—C7	−2.1 (2)	C11—C12—C13—C14	0.2 (4)
N3—N2—C7—C6	174.94 (17)	C12—C13—C14—C9	1.2 (3)
N3—N2—C7—C8	−8.8 (4)	C10—C9—C14—C13	−2.2 (3)
C5—C6—C7—N2	−1.2 (3)	N3—C9—C14—C13	177.49 (18)
C1—C6—C7—N2	179.53 (16)	N2—N3—C15—C16	106.2 (2)
C5—C6—C7—C8	−178.5 (2)	C9—N3—C15—C16	−83.3 (2)
C1—C6—C7—C8	2.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1	0.97	2.21	2.916 (2)	128
N1—H1A···O1i	0.86	1.99	2.844 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1	0.97	2.21	2.916 (2)	128
N1—H1A⋯O1i	0.86	1.99	2.844 (2)	172

Symmetry code: (i) .