3-[(E)-Benzyl-idene]indolin-2-one.

In the title indolin-2-one derivative, C(15)H(11)NO, the phenyl ring and the oxoindoline fused-ring system (r.m.s. deviation = 0.011 Å) are aligned at 48.52 (6)°. In the crystal, inversion-related mol-ecules form an N-H⋯O hydrogen-bonded dimer via an eight-membered {⋯HNCO}(2) synthon. The dimeric aggregates are linked into a three-dimensional architecture via C-H⋯O and π-π inter-actions between the five- and six-membered rings of the fused ring system, with an inter-centroid distance of 3.4538 (8) Å.

Related literature

For the structure of the Z-isomer of the title compound, see: Milanesio et al. (2000 ▶). For background to related thia­zoles, see: Badahdaha et al. (2009 ▶).

Experimental

Crystal data

C15H11NO

M = 221.25

Monoclinic,

a = 3.9796 (3) Å

b = 22.2266 (19) Å

c = 12.2484 (10) Å

β = 95.027 (1)°

V = 1079.24 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

6831 measured reflections

2460 independent reflections

2153 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.03

2460 reflections

158 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024762/mw2072sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024762/mw2072Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024762/mw2072Isup3.cml

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

C15H11NO	F(000) = 464
Mr = 221.25	Dx = 1.362 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3166 reflections
a = 3.9796 (3) Å	θ = 2.5–28.3°
b = 22.2266 (19) Å	µ = 0.09 mm−1
c = 12.2484 (10) Å	T = 100 K
β = 95.027 (1)°	Prism, orange
V = 1079.24 (15) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	2153 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
ω scans	h = −3→5
6831 measured reflections	k = −28→28
2460 independent reflections	l = −15→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2809P] where P = (Fo2 + 2Fc2)/3
2460 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.5372 (2)	0.58258 (4)	0.53379 (7)	0.0236 (2)
N1	0.7366 (3)	0.52725 (4)	0.39388 (8)	0.0183 (2)
H1N	0.668 (4)	0.4920 (5)	0.4133 (12)	0.032 (4)*
C1	0.8893 (3)	0.53924 (5)	0.29780 (9)	0.0167 (2)
C2	0.9905 (3)	0.49792 (5)	0.22291 (10)	0.0194 (3)
H2	0.9556	0.4560	0.2321	0.023*
C3	1.1456 (3)	0.52014 (6)	0.13341 (10)	0.0211 (3)
H3	1.2194	0.4929	0.0808	0.025*
C4	1.1938 (3)	0.58149 (6)	0.11990 (10)	0.0207 (3)
H4	1.2987	0.5956	0.0580	0.025*
C5	1.0897 (3)	0.62256 (5)	0.19619 (9)	0.0184 (2)
H5	1.1241	0.6645	0.1866	0.022*
C6	0.9350 (3)	0.60162 (5)	0.28646 (9)	0.0159 (2)
C7	0.8052 (3)	0.62991 (5)	0.38267 (9)	0.0167 (2)
C8	0.6761 (3)	0.57888 (5)	0.44818 (9)	0.0180 (3)
C9	0.7925 (3)	0.68631 (5)	0.42166 (9)	0.0176 (2)
H9	0.7175	0.6901	0.4929	0.021*
C10	0.8793 (3)	0.74284 (5)	0.36866 (9)	0.0167 (2)
C11	0.7759 (3)	0.75418 (5)	0.25856 (9)	0.0179 (2)
H11	0.6540	0.7243	0.2161	0.021*
C12	0.8496 (3)	0.80862 (5)	0.21070 (10)	0.0194 (3)
H12	0.7756	0.8160	0.1360	0.023*
C13	1.0311 (3)	0.85235 (5)	0.27155 (10)	0.0199 (3)
H13	1.0862	0.8892	0.2382	0.024*
C14	1.1317 (3)	0.84202 (5)	0.38124 (10)	0.0203 (3)
H14	1.2557	0.8719	0.4231	0.024*
C15	1.0516 (3)	0.78813 (5)	0.43000 (9)	0.0191 (3)
H15	1.1145	0.7819	0.5058	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0347 (5)	0.0183 (4)	0.0189 (4)	−0.0028 (4)	0.0088 (4)	0.0011 (3)
N1	0.0234 (5)	0.0130 (5)	0.0186 (5)	−0.0015 (4)	0.0024 (4)	0.0020 (4)
C1	0.0150 (5)	0.0178 (6)	0.0167 (5)	0.0001 (4)	−0.0015 (4)	0.0013 (4)
C2	0.0178 (5)	0.0177 (6)	0.0222 (6)	0.0018 (4)	−0.0010 (4)	−0.0010 (4)
C3	0.0191 (5)	0.0246 (6)	0.0193 (6)	0.0039 (5)	0.0001 (4)	−0.0044 (5)
C4	0.0179 (5)	0.0265 (6)	0.0179 (6)	0.0008 (5)	0.0019 (4)	0.0008 (5)
C5	0.0164 (5)	0.0190 (6)	0.0196 (6)	−0.0018 (4)	0.0008 (4)	0.0016 (4)
C6	0.0146 (5)	0.0163 (5)	0.0163 (5)	−0.0004 (4)	−0.0017 (4)	−0.0002 (4)
C7	0.0177 (5)	0.0170 (6)	0.0153 (5)	−0.0017 (4)	0.0004 (4)	0.0025 (4)
C8	0.0209 (6)	0.0157 (6)	0.0171 (5)	−0.0015 (4)	−0.0006 (4)	0.0016 (4)
C9	0.0200 (5)	0.0180 (6)	0.0148 (5)	−0.0005 (4)	0.0020 (4)	0.0006 (4)
C10	0.0172 (5)	0.0146 (5)	0.0188 (5)	0.0008 (4)	0.0046 (4)	−0.0005 (4)
C11	0.0183 (5)	0.0164 (5)	0.0189 (6)	−0.0009 (4)	0.0018 (4)	−0.0009 (4)
C12	0.0200 (6)	0.0202 (6)	0.0181 (5)	0.0015 (4)	0.0032 (4)	0.0022 (4)
C13	0.0196 (6)	0.0151 (5)	0.0255 (6)	−0.0002 (4)	0.0058 (4)	0.0028 (4)
C14	0.0214 (6)	0.0152 (5)	0.0244 (6)	−0.0020 (4)	0.0025 (4)	−0.0038 (4)
C15	0.0224 (6)	0.0182 (6)	0.0167 (5)	0.0015 (4)	0.0018 (4)	−0.0013 (4)

O1—C8	1.2302 (14)	C7—C9	1.3439 (16)
N1—C8	1.3585 (15)	C7—C8	1.5054 (15)
N1—C1	1.3968 (14)	C9—C10	1.4693 (15)
N1—H1N	0.87 (1)	C9—H9	0.9500
C1—C2	1.3825 (16)	C10—C11	1.3978 (16)
C1—C6	1.4068 (16)	C10—C15	1.3993 (16)
C2—C3	1.3946 (17)	C11—C12	1.3871 (16)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.3890 (18)	C12—C13	1.3884 (17)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.3950 (16)	C13—C14	1.3871 (17)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3919 (15)	C14—C15	1.3881 (16)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.4689 (15)	C15—H15	0.9500
C8—N1—C1	111.10 (9)	O1—C8—N1	125.86 (10)
C8—N1—H1N	123.7 (11)	O1—C8—C7	127.13 (10)
C1—N1—H1N	124.9 (11)	N1—C8—C7	106.99 (10)
C2—C1—N1	127.28 (11)	C7—C9—C10	128.54 (10)
C2—C1—C6	122.79 (11)	C7—C9—H9	115.7
N1—C1—C6	109.93 (10)	C10—C9—H9	115.7
C1—C2—C3	117.44 (11)	C11—C10—C15	118.50 (10)
C1—C2—H2	121.3	C11—C10—C9	121.32 (10)
C3—C2—H2	121.3	C15—C10—C9	120.08 (10)
C4—C3—C2	121.10 (11)	C12—C11—C10	120.65 (11)
C4—C3—H3	119.4	C12—C11—H11	119.7
C2—C3—H3	119.4	C10—C11—H11	119.7
C3—C4—C5	120.69 (11)	C13—C12—C11	120.20 (11)
C3—C4—H4	119.7	C13—C12—H12	119.9
C5—C4—H4	119.7	C11—C12—H12	119.9
C4—C5—C6	119.42 (11)	C14—C13—C12	119.78 (11)
C4—C5—H5	120.3	C14—C13—H13	120.1
C6—C5—H5	120.3	C12—C13—H13	120.1
C5—C6—C1	118.55 (10)	C13—C14—C15	120.12 (11)
C5—C6—C7	134.85 (11)	C13—C14—H14	119.9
C1—C6—C7	106.56 (10)	C15—C14—H14	119.9
C9—C7—C6	135.33 (11)	C14—C15—C10	120.67 (11)
C9—C7—C8	119.22 (10)	C14—C15—H15	119.7
C6—C7—C8	105.40 (9)	C10—C15—H15	119.7
C8—N1—C1—C2	179.20 (11)	C1—N1—C8—C7	−0.80 (13)
C8—N1—C1—C6	0.09 (13)	C9—C7—C8—O1	4.54 (18)
N1—C1—C2—C3	−178.59 (11)	C6—C7—C8—O1	−177.79 (11)
C6—C1—C2—C3	0.41 (16)	C9—C7—C8—N1	−176.49 (10)
C1—C2—C3—C4	−0.48 (17)	C6—C7—C8—N1	1.18 (12)
C2—C3—C4—C5	0.40 (17)	C6—C7—C9—C10	8.2 (2)
C3—C4—C5—C6	−0.23 (17)	C8—C7—C9—C10	−175.00 (11)
C4—C5—C6—C1	0.15 (16)	C7—C9—C10—C11	43.93 (18)
C4—C5—C6—C7	177.75 (11)	C7—C9—C10—C15	−139.89 (13)
C2—C1—C6—C5	−0.25 (16)	C15—C10—C11—C12	1.47 (17)
N1—C1—C6—C5	178.91 (10)	C9—C10—C11—C12	177.71 (10)
C2—C1—C6—C7	−178.47 (10)	C10—C11—C12—C13	0.77 (17)
N1—C1—C6—C7	0.68 (12)	C11—C12—C13—C14	−1.57 (17)
C5—C6—C7—C9	−1.8 (2)	C12—C13—C14—C15	0.09 (18)
C1—C6—C7—C9	175.99 (13)	C13—C14—C15—C10	2.20 (18)
C5—C6—C7—C8	−178.91 (12)	C11—C10—C15—C14	−2.95 (17)
C1—C6—C7—C8	−1.11 (11)	C9—C10—C15—C14	−179.24 (10)
C1—N1—C8—O1	178.19 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (1)	1.98 (1)	2.846 (1)	172 (2)
C13—H13···O1ii	0.95	2.57	3.2535 (15)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (1)	1.98 (1)	2.846 (1)	172 (2)
C13—H13⋯O1ii	0.95	2.57	3.2535 (15)	129

Symmetry codes: (i) ; (ii) .