(Z)-3-[(E)-3-Phenyl-allyl-idene]indolin-2-one.

The title compound, C(17)H(13)NO, synthesized to be tested for neuroprotective activities, consists of an indoline and a phenyl-allyl-idene unit with a dihedral angle of 9.0 (1)° between the two ring systems. There are two independent mol-ecules in the asymmetric unit which are connected into a dimer by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the pharmacological properties of 3-substituted indoline-2-ones, see: Sun et al. (2003 ▶); Andreani et al. (2006 ▶); Johnson et al. (2005 ▶). For the synthesis and neuroprotective activities of a series of 3-substituted indoline-2-one derivatives, see: Balderamos et al. (2008 ▶). For the original synthesis of the title compound, see: Elliott & Rivers (1964 ▶). For modified synthetic methods, see: Tacconi & Marinone (1968 ▶); Villemin & Martin (1998 ▶). For the crystal structures of related compounds, see: Zhang et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C17H13NO

M = 247.28

Monoclinic,

a = 5.8373 (4) Å

b = 15.3294 (11) Å

c = 14.6516 (10) Å

β = 94.312 (1)°

V = 1307.35 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 (2) K

0.38 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.994

12503 measured reflections

3282 independent reflections

2386 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.132

S = 1.11

3282 reflections

343 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker 1997 ▶); cell refinement: SAINT (Bruker 1997 ▶); 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 and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002037/bt2843sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002037/bt2843Isup2.hkl

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

C17H13NO	F(000) = 520
Mr = 247.28	Dx = 1.256 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.8373 (4) Å	Cell parameters from 3505 reflections
b = 15.3294 (11) Å	θ = 2.7–28.1°
c = 14.6516 (10) Å	µ = 0.08 mm−1
β = 94.312 (1)°	T = 296 K
V = 1307.35 (16) Å3	Plates, orange
Z = 4	0.38 × 0.21 × 0.08 mm

Bruker SMART APEX diffractometer	3282 independent reflections
Radiation source: fine-focus sealed tube	2386 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 83.33 pixels mm-1	θmax = 28.3°, θmin = 1.4°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→20
Tmin = 0.971, Tmax = 0.994	l = −19→19
12503 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3
3282 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.15 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
N1	0.4059 (5)	0.95163 (18)	0.38623 (17)	0.0543 (7)
H1	0.2755	0.9773	0.3761	0.065*
C2	0.5085 (5)	0.9366 (2)	0.4708 (2)	0.0489 (8)
O2	0.4320 (4)	0.95989 (17)	0.54301 (15)	0.0629 (7)
C3	0.7271 (5)	0.8900 (2)	0.4579 (2)	0.0472 (8)
C4	0.8935 (6)	0.8445 (2)	0.3042 (2)	0.0570 (9)
H4	1.0253	0.8175	0.3303	0.068*
C5	0.8528 (7)	0.8490 (3)	0.2103 (3)	0.0688 (10)
H5	0.9586	0.8254	0.1729	0.083*
C6	0.6563 (7)	0.8883 (3)	0.1715 (2)	0.0710 (11)
H6	0.6319	0.8903	0.1081	0.085*
C7	0.4945 (6)	0.9250 (2)	0.2242 (2)	0.0616 (9)
H7	0.3628	0.9516	0.1976	0.074*
C8	0.5369 (6)	0.9204 (2)	0.3177 (2)	0.0502 (8)
C9	0.7351 (5)	0.8807 (2)	0.3587 (2)	0.0462 (8)
C10	0.8870 (6)	0.8656 (2)	0.5242 (2)	0.0516 (8)
H10	1.0145	0.8360	0.5057	0.062*
C11	0.8796 (6)	0.8809 (2)	0.6199 (2)	0.0533 (9)
H11	0.7472	0.9045	0.6414	0.064*
C12	1.0558 (6)	0.8623 (2)	0.6795 (2)	0.0561 (9)
H12	1.1814	0.8356	0.6557	0.067*
C13	1.0757 (6)	0.8790 (2)	0.7785 (2)	0.0537 (8)
C14	0.9034 (7)	0.9174 (2)	0.8247 (2)	0.0654 (10)
H14	0.7671	0.9344	0.7927	0.078*
C15	0.9330 (8)	0.9305 (3)	0.9174 (3)	0.0809 (12)
H15	0.8159	0.9563	0.9476	0.097*
C16	1.1324 (10)	0.9062 (3)	0.9662 (3)	0.0879 (14)
H16	1.1517	0.9164	1.0289	0.105*
C17	1.3015 (9)	0.8671 (4)	0.9220 (3)	0.0892 (14)
H17	1.4350	0.8485	0.9549	0.107*
C18	1.2756 (7)	0.8550 (3)	0.8289 (3)	0.0686 (10)
H18	1.3949	0.8302	0.7992	0.082*
N21	1.0612 (5)	0.08155 (18)	0.53233 (18)	0.0536 (7)
H21	1.1927	0.0565	0.5416	0.064*
C22	0.9524 (5)	0.0958 (2)	0.4481 (2)	0.0492 (8)
O22	1.0232 (4)	0.07199 (16)	0.37516 (15)	0.0594 (6)
C23	0.7335 (5)	0.1433 (2)	0.4633 (2)	0.0456 (8)
C24	0.5755 (6)	0.1884 (2)	0.6182 (2)	0.0556 (9)
H24	0.4423	0.2150	0.5930	0.067*
C25	0.6208 (7)	0.1840 (2)	0.7120 (2)	0.0613 (9)
H25	0.5180	0.2084	0.7502	0.074*
C26	0.8194 (7)	0.1435 (3)	0.7497 (2)	0.0622 (10)
H26	0.8460	0.1403	0.8130	0.075*
C27	0.9781 (6)	0.1077 (2)	0.6946 (2)	0.0567 (8)
H27	1.1115	0.0810	0.7197	0.068*
C28	0.9305 (6)	0.1132 (2)	0.6021 (2)	0.0482 (8)
C29	0.7319 (5)	0.1524 (2)	0.5624 (2)	0.0456 (8)
C30	0.5699 (6)	0.1654 (2)	0.3983 (2)	0.0530 (8)
H30	0.4411	0.1931	0.4183	0.064*
C31	0.5698 (6)	0.1515 (2)	0.3022 (2)	0.0528 (8)
H31	0.7001	0.1279	0.2790	0.063*
C32	0.3890 (6)	0.1712 (2)	0.2440 (2)	0.0559 (9)
H32	0.2614	0.1940	0.2699	0.067*
C33	0.3687 (6)	0.1611 (2)	0.1446 (2)	0.0522 (8)
C34	0.5387 (7)	0.1255 (3)	0.0959 (3)	0.0687 (10)
H34	0.6731	0.1050	0.1268	0.082*
C35	0.5111 (8)	0.1201 (3)	0.0017 (3)	0.0817 (12)
H35	0.6266	0.0957	−0.0305	0.098*
C36	0.3149 (9)	0.1503 (3)	−0.0446 (3)	0.0852 (13)
H36	0.2974	0.1468	−0.1081	0.102*
C37	0.1474 (8)	0.1852 (3)	0.0019 (3)	0.0829 (13)
H37	0.0140	0.2058	−0.0297	0.099*
C38	0.1718 (6)	0.1907 (3)	0.0951 (2)	0.0672 (10)
H38	0.0538	0.2148	0.1262	0.081*

	U11	U22	U33	U12	U13	U23
N1	0.0485 (14)	0.0618 (19)	0.0516 (16)	0.0099 (13)	−0.0044 (12)	−0.0011 (13)
C2	0.0476 (17)	0.0503 (19)	0.0489 (19)	−0.0030 (15)	0.0037 (15)	0.0000 (15)
O2	0.0579 (14)	0.0837 (19)	0.0471 (14)	0.0140 (13)	0.0039 (11)	−0.0010 (13)
C3	0.0504 (18)	0.0450 (19)	0.0457 (19)	−0.0058 (14)	0.0016 (15)	−0.0018 (14)
C4	0.0536 (18)	0.062 (2)	0.055 (2)	0.0036 (17)	0.0005 (16)	−0.0079 (17)
C5	0.074 (2)	0.078 (3)	0.056 (2)	0.000 (2)	0.0158 (19)	−0.0088 (19)
C6	0.087 (3)	0.084 (3)	0.042 (2)	−0.002 (2)	0.0042 (19)	−0.0036 (19)
C7	0.072 (2)	0.062 (2)	0.049 (2)	0.0020 (18)	−0.0097 (17)	0.0047 (17)
C8	0.0557 (18)	0.0449 (18)	0.049 (2)	−0.0053 (15)	−0.0015 (15)	−0.0026 (15)
C9	0.0484 (17)	0.0418 (17)	0.0475 (19)	−0.0043 (15)	−0.0019 (14)	0.0002 (15)
C10	0.0512 (18)	0.052 (2)	0.051 (2)	0.0020 (16)	0.0014 (15)	0.0002 (16)
C11	0.0520 (18)	0.055 (2)	0.052 (2)	0.0042 (16)	0.0013 (16)	0.0052 (17)
C12	0.058 (2)	0.061 (2)	0.050 (2)	0.0075 (17)	0.0041 (16)	0.0026 (17)
C13	0.0572 (19)	0.057 (2)	0.0453 (19)	−0.0013 (17)	−0.0037 (15)	0.0055 (16)
C14	0.070 (2)	0.070 (2)	0.056 (2)	0.0124 (19)	0.0078 (18)	0.0073 (19)
C15	0.097 (3)	0.083 (3)	0.066 (3)	0.005 (2)	0.024 (2)	0.000 (2)
C16	0.113 (4)	0.096 (3)	0.053 (2)	−0.009 (3)	−0.002 (3)	−0.011 (2)
C17	0.089 (3)	0.113 (4)	0.062 (3)	−0.005 (3)	−0.017 (2)	−0.002 (3)
C18	0.062 (2)	0.087 (3)	0.055 (2)	0.002 (2)	−0.0039 (17)	−0.006 (2)
N21	0.0479 (15)	0.0640 (19)	0.0480 (16)	0.0086 (13)	−0.0024 (12)	−0.0002 (14)
C22	0.0486 (17)	0.0484 (19)	0.0497 (19)	−0.0011 (14)	−0.0016 (14)	0.0023 (14)
O22	0.0573 (13)	0.0792 (17)	0.0421 (13)	0.0106 (12)	0.0067 (10)	−0.0029 (11)
C23	0.0466 (17)	0.0457 (18)	0.0442 (18)	−0.0005 (14)	0.0008 (14)	0.0038 (14)
C24	0.055 (2)	0.059 (2)	0.054 (2)	0.0009 (16)	0.0071 (16)	−0.0014 (16)
C25	0.065 (2)	0.068 (2)	0.052 (2)	−0.0025 (18)	0.0134 (17)	−0.0099 (18)
C26	0.083 (2)	0.063 (2)	0.0400 (19)	−0.003 (2)	0.0013 (17)	−0.0005 (17)
C27	0.062 (2)	0.060 (2)	0.0467 (19)	0.0022 (17)	−0.0053 (15)	−0.0006 (17)
C28	0.0514 (18)	0.0470 (18)	0.0459 (18)	−0.0026 (16)	0.0016 (15)	−0.0043 (15)
C29	0.0500 (17)	0.0451 (18)	0.0416 (18)	−0.0027 (15)	0.0026 (14)	−0.0012 (15)
C30	0.0478 (17)	0.059 (2)	0.053 (2)	0.0019 (16)	0.0040 (15)	0.0051 (17)
C31	0.0538 (18)	0.058 (2)	0.0463 (19)	0.0003 (17)	−0.0006 (15)	0.0047 (16)
C32	0.0533 (19)	0.063 (2)	0.052 (2)	0.0010 (17)	0.0059 (16)	0.0080 (17)
C33	0.0563 (19)	0.053 (2)	0.0476 (19)	−0.0018 (17)	0.0057 (15)	0.0025 (15)
C34	0.070 (2)	0.076 (3)	0.060 (2)	0.008 (2)	0.0065 (19)	0.008 (2)
C35	0.090 (3)	0.092 (3)	0.066 (2)	0.010 (3)	0.020 (2)	−0.008 (2)
C36	0.105 (3)	0.104 (3)	0.045 (2)	−0.005 (3)	−0.001 (2)	−0.002 (2)
C37	0.085 (3)	0.105 (3)	0.056 (2)	0.010 (3)	−0.013 (2)	−0.001 (2)
C38	0.063 (2)	0.080 (3)	0.057 (2)	0.0100 (19)	−0.0065 (18)	0.000 (2)

N1—C2	1.355 (4)	N21—C22	1.362 (4)
N1—C8	1.392 (4)	N21—C28	1.407 (4)
N1—H1	0.8600	N21—H21	0.8600
C2—O2	1.232 (3)	C22—O22	1.230 (4)
C2—C3	1.487 (4)	C22—C23	1.501 (4)
C3—C10	1.348 (4)	C23—C30	1.341 (4)
C3—C9	1.464 (4)	C23—C29	1.460 (4)
C4—C5	1.380 (5)	C24—C25	1.380 (5)
C4—C9	1.383 (5)	C24—C29	1.386 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.380 (6)	C25—C26	1.392 (5)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.383 (5)	C26—C27	1.386 (5)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.374 (4)	C27—C28	1.366 (4)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.402 (4)	C28—C29	1.394 (4)
C10—C11	1.426 (5)	C30—C31	1.423 (4)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.328 (4)	C31—C32	1.341 (4)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.469 (4)	C32—C33	1.460 (4)
C12—H12	0.9300	C32—H32	0.9300
C13—C18	1.384 (5)	C33—C34	1.377 (5)
C13—C14	1.386 (5)	C33—C38	1.388 (5)
C14—C15	1.370 (5)	C34—C35	1.380 (5)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.371 (6)	C35—C36	1.368 (6)
C15—H15	0.9300	C35—H35	0.9300
C16—C17	1.360 (7)	C36—C37	1.344 (6)
C16—H16	0.9300	C36—H36	0.9300
C17—C18	1.374 (5)	C37—C38	1.365 (5)
C17—H17	0.9300	C37—H37	0.9300
C18—H18	0.9300	C38—H38	0.9300
C2—N1—C8	111.8 (3)	C22—N21—C28	111.2 (3)
C2—N1—H1	124.1	C22—N21—H21	124.4
C8—N1—H1	124.1	C28—N21—H21	124.4
O2—C2—N1	124.9 (3)	O22—C22—N21	125.1 (3)
O2—C2—C3	128.2 (3)	O22—C22—C23	128.1 (3)
N1—C2—C3	106.8 (3)	N21—C22—C23	106.7 (3)
C10—C3—C9	128.0 (3)	C30—C23—C29	128.7 (3)
C10—C3—C2	126.5 (3)	C30—C23—C22	125.9 (3)
C9—C3—C2	105.4 (3)	C29—C23—C22	105.2 (3)
C5—C4—C9	118.9 (3)	C25—C24—C29	118.8 (3)
C5—C4—H4	120.6	C25—C24—H24	120.6
C9—C4—H4	120.6	C29—C24—H24	120.6
C4—C5—C6	120.5 (4)	C24—C25—C26	120.5 (3)
C4—C5—H5	119.7	C24—C25—H25	119.7
C6—C5—H5	119.7	C26—C25—H25	119.7
C5—C6—C7	121.9 (3)	C27—C26—C25	121.2 (3)
C5—C6—H6	119.0	C27—C26—H26	119.4
C7—C6—H6	119.0	C25—C26—H26	119.4
C8—C7—C6	117.1 (3)	C28—C27—C26	117.3 (3)
C8—C7—H7	121.4	C28—C27—H27	121.4
C6—C7—H7	121.4	C26—C27—H27	121.4
C7—C8—N1	129.3 (3)	C27—C28—C29	122.8 (3)
C7—C8—C9	122.0 (3)	C27—C28—N21	128.3 (3)
N1—C8—C9	108.7 (3)	C29—C28—N21	108.9 (3)
C4—C9—C8	119.5 (3)	C24—C29—C28	119.3 (3)
C4—C9—C3	133.2 (3)	C24—C29—C23	132.8 (3)
C8—C9—C3	107.2 (3)	C28—C29—C23	107.9 (3)
C3—C10—C11	126.4 (3)	C23—C30—C31	127.7 (3)
C3—C10—H10	116.8	C23—C30—H30	116.1
C11—C10—H10	116.8	C31—C30—H30	116.1
C12—C11—C10	122.2 (3)	C32—C31—C30	122.5 (3)
C12—C11—H11	118.9	C32—C31—H31	118.7
C10—C11—H11	118.9	C30—C31—H31	118.7
C11—C12—C13	127.7 (3)	C31—C32—C33	127.7 (3)
C11—C12—H12	116.2	C31—C32—H32	116.1
C13—C12—H12	116.2	C33—C32—H32	116.1
C18—C13—C14	117.8 (3)	C34—C33—C38	117.4 (3)
C18—C13—C12	118.8 (3)	C34—C33—C32	123.4 (3)
C14—C13—C12	123.4 (3)	C38—C33—C32	119.2 (3)
C15—C14—C13	120.3 (4)	C33—C34—C35	120.5 (4)
C15—C14—H14	119.8	C33—C34—H34	119.8
C13—C14—H14	119.8	C35—C34—H34	119.8
C14—C15—C16	121.1 (4)	C36—C35—C34	120.4 (4)
C14—C15—H15	119.5	C36—C35—H35	119.8
C16—C15—H15	119.5	C34—C35—H35	119.8
C17—C16—C15	119.3 (4)	C37—C36—C35	119.8 (4)
C17—C16—H16	120.4	C37—C36—H36	120.1
C15—C16—H16	120.4	C35—C36—H36	120.1
C16—C17—C18	120.2 (4)	C36—C37—C38	120.4 (4)
C16—C17—H17	119.9	C36—C37—H37	119.8
C18—C17—H17	119.9	C38—C37—H37	119.8
C17—C18—C13	121.3 (4)	C37—C38—C33	121.5 (4)
C17—C18—H18	119.3	C37—C38—H38	119.3
C13—C18—H18	119.3	C33—C38—H38	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O2i	0.86	2.03	2.852 (3)	159
N1—H1···O22ii	0.86	2.07	2.893 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O2i	0.86	2.03	2.852 (3)	159
N1—H1⋯O22ii	0.86	2.07	2.893 (3)	161

Symmetry codes: (i) ; (ii) .