3-(Diphenyl-methyl-idene)indolin-2-one.

The title mol-ecule, C(21)H(15)NO, has an indoline-2-one and two benzene substituent groups which are arranged in a propeller-like fashion around the central C atom. The dihedral angle between the two benzene rings is 73.32 (16)° and those between the benzene rings and the indoline-2-one group are 76.54 (14) and 67.69 (14)°. In the crystal, there is an inter-molecular N-H⋯O hydrogen-bonding inter-action, which links the mol-ecules into chains extending along c.

Related literature

For general background to indoline-2-one and its derivatives, see: Colgan et al. (1996 ▶). For the use of n class="Chemical">indoline-2-one as a precursor for the synthesis of organic luminescent mol­ecules, see: Ji et al. (2010 ▶). For a related structure, see: Spencer et al. (2010 ▶).

Experimental

Crystal data

C21H15NO

M = 297.34

Orthorhombic,

a = 11.0679 (11) Å

b = 17.6465 (16) Å

c = 7.8835 (6) Å

V = 1539.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.46 × 0.40 × 0.38 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.971

9094 measured reflections

2072 independent reflections

1105 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.06

2072 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028467/zs2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028467/zs2123Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028467/zs2123Isup3.cml

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

C21H15NO	F(000) = 624
Mr = 297.34	Dx = 1.283 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1702 reflections
a = 11.0679 (11) Å	θ = 2.8–21.0°
b = 17.6465 (16) Å	µ = 0.08 mm−1
c = 7.8835 (6) Å	T = 298 K
V = 1539.7 (2) Å3	Block, yellow
Z = 4	0.46 × 0.40 × 0.38 mm

Bruker SMART CCD area-detector diffractometer	2072 independent reflections
Radiation source: fine-focus sealed tube	1105 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.965, Tmax = 0.971	k = −23→15
9094 measured reflections	l = −9→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3
2072 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.15 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 > 2sigma(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
N1	0.4749 (2)	0.42487 (13)	0.0945 (4)	0.0564 (7)
H1	0.4439	0.4611	0.0361	0.068*
O1	0.5893 (2)	0.49677 (11)	0.2730 (3)	0.0631 (6)
C1	0.5549 (3)	0.43506 (16)	0.2223 (4)	0.0481 (8)
C2	0.5846 (3)	0.35719 (15)	0.2880 (4)	0.0415 (7)
C3	0.5159 (2)	0.30486 (15)	0.1807 (4)	0.0424 (7)
C4	0.4489 (3)	0.34850 (16)	0.0692 (4)	0.0500 (8)
C5	0.3681 (3)	0.3183 (2)	−0.0444 (5)	0.0695 (10)
H5	0.3233	0.3490	−0.1167	0.083*
C6	0.3564 (3)	0.2406 (2)	−0.0468 (5)	0.0728 (11)
H6	0.3012	0.2184	−0.1206	0.087*
C7	0.4244 (3)	0.19516 (18)	0.0577 (5)	0.0612 (9)
H7	0.4163	0.1428	0.0513	0.073*
C8	0.5051 (3)	0.22649 (16)	0.1725 (5)	0.0523 (8)
H8	0.5511	0.1956	0.2428	0.063*
C9	0.6510 (2)	0.34259 (15)	0.4264 (4)	0.0432 (7)
C10	0.6611 (2)	0.26418 (15)	0.4946 (4)	0.0413 (7)
C11	0.7606 (3)	0.22020 (16)	0.4565 (4)	0.0549 (9)
H11	0.8228	0.2403	0.3912	0.066*
C12	0.7683 (3)	0.14681 (17)	0.5144 (5)	0.0624 (10)
H12	0.8355	0.1176	0.4873	0.075*
C13	0.6788 (3)	0.11674 (17)	0.6108 (5)	0.0607 (9)
H13	0.6844	0.0671	0.6496	0.073*
C14	0.5802 (3)	0.15989 (18)	0.6504 (5)	0.0643 (10)
H14	0.5187	0.1393	0.7162	0.077*
C15	0.5712 (3)	0.23353 (16)	0.5939 (4)	0.0553 (8)
H15	0.5042	0.2626	0.6230	0.066*
C16	0.7198 (3)	0.40090 (16)	0.5234 (4)	0.0458 (8)
C17	0.6978 (3)	0.41196 (17)	0.6938 (4)	0.0562 (9)
H17	0.6395	0.3828	0.7480	0.067*
C18	0.7609 (4)	0.46540 (19)	0.7850 (5)	0.0704 (10)
H18	0.7447	0.4725	0.8997	0.085*
C19	0.8472 (3)	0.50795 (19)	0.7065 (6)	0.0702 (11)
H19	0.8891	0.5445	0.7677	0.084*
C20	0.8726 (3)	0.49722 (19)	0.5391 (6)	0.0711 (11)
H20	0.9326	0.5258	0.4868	0.085*
C21	0.8093 (3)	0.44404 (17)	0.4473 (5)	0.0611 (9)
H21	0.8267	0.4370	0.3330	0.073*

	U11	U22	U33	U12	U13	U23
N1	0.0730 (17)	0.0451 (15)	0.0510 (16)	0.0083 (12)	−0.0133 (16)	0.0055 (14)
O1	0.0791 (14)	0.0400 (12)	0.0703 (16)	−0.0001 (10)	−0.0080 (14)	−0.0016 (12)
C1	0.0563 (18)	0.0438 (17)	0.044 (2)	0.0028 (15)	0.0026 (16)	−0.0005 (16)
C2	0.0490 (15)	0.0380 (15)	0.0377 (16)	0.0044 (13)	0.0007 (14)	0.0011 (14)
C3	0.0458 (16)	0.0428 (16)	0.0385 (16)	0.0023 (13)	0.0028 (14)	−0.0016 (15)
C4	0.0557 (17)	0.0495 (18)	0.0448 (19)	0.0039 (15)	−0.0030 (15)	−0.0006 (16)
C5	0.083 (2)	0.072 (2)	0.054 (2)	0.005 (2)	−0.024 (2)	−0.002 (2)
C6	0.081 (2)	0.079 (3)	0.059 (2)	−0.006 (2)	−0.020 (2)	−0.018 (2)
C7	0.073 (2)	0.0549 (19)	0.056 (2)	−0.0049 (18)	−0.0027 (19)	−0.0126 (19)
C8	0.0607 (18)	0.0460 (17)	0.0503 (19)	0.0034 (15)	−0.0020 (17)	−0.0053 (16)
C9	0.0449 (16)	0.0387 (16)	0.0459 (18)	0.0038 (12)	0.0034 (15)	−0.0024 (14)
C10	0.0434 (15)	0.0387 (15)	0.0418 (18)	−0.0022 (13)	−0.0061 (15)	−0.0008 (14)
C11	0.0485 (17)	0.0464 (17)	0.070 (2)	−0.0011 (14)	0.0129 (18)	0.0042 (18)
C12	0.0601 (19)	0.0455 (19)	0.082 (3)	0.0089 (16)	−0.003 (2)	−0.0042 (18)
C13	0.084 (2)	0.0418 (18)	0.057 (2)	−0.0001 (18)	−0.009 (2)	0.0046 (18)
C14	0.075 (2)	0.056 (2)	0.062 (2)	−0.0100 (18)	0.012 (2)	0.0052 (18)
C15	0.0547 (17)	0.0511 (18)	0.060 (2)	0.0013 (15)	0.0083 (18)	0.0024 (18)
C16	0.0508 (16)	0.0371 (17)	0.050 (2)	0.0042 (14)	−0.0058 (16)	−0.0019 (14)
C17	0.072 (2)	0.0472 (19)	0.049 (2)	0.0000 (16)	−0.0001 (18)	0.0011 (16)
C18	0.101 (3)	0.053 (2)	0.057 (2)	0.001 (2)	−0.014 (2)	−0.0124 (19)
C19	0.078 (2)	0.050 (2)	0.083 (3)	−0.0047 (18)	−0.027 (2)	−0.015 (2)
C20	0.067 (2)	0.060 (2)	0.086 (3)	−0.0166 (18)	−0.004 (2)	−0.010 (2)
C21	0.065 (2)	0.060 (2)	0.058 (2)	−0.0122 (17)	0.0040 (19)	−0.0051 (18)

N1—C1	1.353 (4)	C11—C12	1.376 (4)
N1—C4	1.392 (4)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.356 (4)
O1—C1	1.221 (3)	C12—H12	0.9300
C1—C2	1.505 (4)	C13—C14	1.366 (4)
C2—C9	1.341 (4)	C13—H13	0.9300
C2—C3	1.465 (4)	C14—C15	1.377 (4)
C3—C4	1.384 (4)	C14—H14	0.9300
C3—C8	1.390 (4)	C15—H15	0.9300
C4—C5	1.374 (4)	C16—C17	1.379 (4)
C5—C6	1.377 (5)	C16—C21	1.386 (4)
C5—H5	0.9300	C17—C18	1.376 (4)
C6—C7	1.374 (5)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.364 (5)
C7—C8	1.386 (4)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.363 (6)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.489 (4)	C20—C21	1.377 (5)
C9—C16	1.491 (4)	C20—H20	0.9300
C10—C15	1.377 (4)	C21—H21	0.9300
C10—C11	1.380 (4)
C1—N1—C4	111.7 (2)	C12—C11—C10	120.4 (3)
C1—N1—H1	124.1	C12—C11—H11	119.8
C4—N1—H1	124.1	C10—C11—H11	119.8
O1—C1—N1	124.5 (3)	C13—C12—C11	120.6 (3)
O1—C1—C2	129.3 (3)	C13—C12—H12	119.7
N1—C1—C2	106.1 (3)	C11—C12—H12	119.7
C9—C2—C3	129.3 (2)	C12—C13—C14	119.5 (3)
C9—C2—C1	125.1 (3)	C12—C13—H13	120.2
C3—C2—C1	105.3 (2)	C14—C13—H13	120.2
C4—C3—C8	118.6 (3)	C13—C14—C15	120.7 (3)
C4—C3—C2	107.1 (2)	C13—C14—H14	119.7
C8—C3—C2	134.4 (3)	C15—C14—H14	119.7
C5—C4—C3	123.2 (3)	C10—C15—C14	120.1 (3)
C5—C4—N1	127.1 (3)	C10—C15—H15	119.9
C3—C4—N1	109.7 (3)	C14—C15—H15	119.9
C4—C5—C6	117.2 (3)	C17—C16—C21	118.0 (3)
C4—C5—H5	121.4	C17—C16—C9	120.5 (3)
C6—C5—H5	121.4	C21—C16—C9	121.5 (3)
C7—C6—C5	121.4 (3)	C18—C17—C16	121.1 (3)
C7—C6—H6	119.3	C18—C17—H17	119.4
C5—C6—H6	119.3	C16—C17—H17	119.4
C6—C7—C8	120.8 (3)	C19—C18—C17	119.7 (4)
C6—C7—H7	119.6	C19—C18—H18	120.1
C8—C7—H7	119.6	C17—C18—H18	120.1
C7—C8—C3	118.9 (3)	C20—C19—C18	120.5 (4)
C7—C8—H8	120.6	C20—C19—H19	119.8
C3—C8—H8	120.6	C18—C19—H19	119.8
C2—C9—C10	120.9 (3)	C19—C20—C21	119.9 (4)
C2—C9—C16	124.4 (3)	C19—C20—H20	120.0
C10—C9—C16	114.7 (3)	C21—C20—H20	120.0
C15—C10—C11	118.7 (3)	C20—C21—C16	120.7 (4)
C15—C10—C9	121.1 (2)	C20—C21—H21	119.6
C11—C10—C9	120.3 (3)	C16—C21—H21	119.6
C4—N1—C1—O1	−177.5 (3)	C1—C2—C9—C16	−8.8 (4)
C4—N1—C1—C2	−0.1 (3)	C2—C9—C10—C15	−80.4 (4)
O1—C1—C2—C9	4.6 (5)	C16—C9—C10—C15	99.8 (3)
N1—C1—C2—C9	−172.6 (3)	C2—C9—C10—C11	98.5 (3)
O1—C1—C2—C3	178.8 (3)	C16—C9—C10—C11	−81.3 (3)
N1—C1—C2—C3	1.6 (3)	C15—C10—C11—C12	1.1 (4)
C9—C2—C3—C4	171.4 (3)	C9—C10—C11—C12	−177.8 (3)
C1—C2—C3—C4	−2.5 (3)	C10—C11—C12—C13	−0.5 (5)
C9—C2—C3—C8	−7.5 (6)	C11—C12—C13—C14	0.0 (5)
C1—C2—C3—C8	178.6 (3)	C12—C13—C14—C15	−0.2 (5)
C8—C3—C4—C5	2.9 (5)	C11—C10—C15—C14	−1.3 (4)
C2—C3—C4—C5	−176.2 (3)	C9—C10—C15—C14	177.5 (3)
C8—C3—C4—N1	−178.4 (3)	C13—C14—C15—C10	0.9 (5)
C2—C3—C4—N1	2.5 (3)	C2—C9—C16—C17	122.6 (3)
C1—N1—C4—C5	177.1 (3)	C10—C9—C16—C17	−57.6 (4)
C1—N1—C4—C3	−1.6 (4)	C2—C9—C16—C21	−59.1 (4)
C3—C4—C5—C6	−1.1 (5)	C10—C9—C16—C21	120.6 (3)
N1—C4—C5—C6	−179.5 (3)	C21—C16—C17—C18	1.5 (5)
C4—C5—C6—C7	−1.3 (6)	C9—C16—C17—C18	179.8 (3)
C5—C6—C7—C8	1.8 (6)	C16—C17—C18—C19	−0.5 (5)
C6—C7—C8—C3	0.1 (5)	C17—C18—C19—C20	−0.8 (6)
C4—C3—C8—C7	−2.4 (5)	C18—C19—C20—C21	1.2 (6)
C2—C3—C8—C7	176.4 (3)	C19—C20—C21—C16	−0.1 (5)
C3—C2—C9—C10	−1.3 (5)	C17—C16—C21—C20	−1.2 (5)
C1—C2—C9—C10	171.5 (3)	C9—C16—C21—C20	−179.5 (3)
C3—C2—C9—C16	178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.23	2.974 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.23	2.974 (3)	144

Symmetry code: (i) .