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organic compounds
(Z)-3-[(E)-3-Phenylallylidene]indolin-2-one
aDepartment of Chemistry, Southern Methodist University, Dallas, TX 75275, USA
*Correspondence e-mail: hzhang@smu.edu
The title compound, C17H13NO, synthesized to be tested for neuroprotective activities, consists of an indoline and a phenylallylidene unit with a dihedral angle of 9.0 (1)° between the two ring systems. There are two independent molecules in the which are connected into a dimer by intermolecular 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
|
Refinement
|
|
Data collection: SMART (Bruker 1997); cell 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
).
Supporting information
10.1107/S1600536809002037/bt2843sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809002037/bt2843Isup2.hkl
The title compound was synthesized by the condensation of trans- cinnamaldehyde (1 mmol) with 2-oxindole (1 mmol) in ethanol (10 ml) in the presence of catalytic amount of piperidine (0.1 mmol). After refluxing for 3 h, the reaction mixture was left to stand for overnight. The resulting crude solid was filtered, washed with cold ethanol (10 ml) and dried. Orange colored single crystals of the compound suitable for x-ray
were recrystallized from ethanol.All H atoms were placed in calculated positions and included in the final cycles of
using a riding model, with distances N–H = 0.86 Å and C–H = 0.93 Å, and displacement parameters Uiso(H) = 1.2Ueq(N,C). Friedel pairs have been merged prior to refinement.Data collection: SMART (Bruker 1997); cell
SAINT (Bruker 1997); data reduction: SAINT (Bruker 1997); 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 (Sheldrick, 2008) and publCIF (Westrip, 2009).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 monochromator | 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 |
C17H13NO | V = 1307.35 (16) Å3 |
Mr = 247.28 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.8373 (4) Å | µ = 0.08 mm−1 |
b = 15.3294 (11) Å | T = 296 K |
c = 14.6516 (10) Å | 0.38 × 0.21 × 0.08 mm |
β = 94.312 (1)° |
Bruker SMART APEX diffractometer | 3282 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2386 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.994 | Rint = 0.032 |
12503 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 1 restraint |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.17 e Å−3 |
3282 reflections | Δρmin = −0.15 e Å−3 |
343 parameters |
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 |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H13NO |
Mr | 247.28 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 5.8373 (4), 15.3294 (11), 14.6516 (10) |
β (°) | 94.312 (1) |
V (Å3) | 1307.35 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.38 × 0.21 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.971, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12503, 3282, 2386 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.132, 1.11 |
No. of reflections | 3282 |
No. of parameters | 343 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: SMART (Bruker 1997), SAINT (Bruker 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O2i | 0.86 | 2.03 | 2.852 (3) | 158.6 |
N1—H1···O22ii | 0.86 | 2.07 | 2.893 (3) | 160.7 |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z. |
Acknowledgements
The authors are grateful for the grants from the Welch Foundation (N-118) and the DARPA (HR0011–06–1–0032).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
It is known that some 3-substituted indoline-2-ones compounds exhibit a variety of pharmacologically important properties such as protein kinase inhibitors (Sun et al., 2003), anti-tumor agents (Andreani et al., 2006) and neuroprotecting agents (Johnson et al., 2005). For studying the biological properties, a series of 3-substituted indoline-2-one derivatives have been synthesized in our lab and their neuroprotective activities have been tested (Balderamos et al., 2008). The results are very promising. To expand our research, a few known compounds were made for test purpose. The title compound was first made by Elliott & Rivers (1964), and modified synthetic methods were reported later (Tacconi & Marinone, 1968; Villemin & Martin, 1998). As a part of our studies on the relationship between the biological activities and solid structures a couple of crystal structures of the derivatives have been carried out (Zhang, et al., 2008, 2009). The title compound consists an indoline and a phenylallylidene unit. The two aromatic rings are slightly twisted with a dihedral angle of 9.0 (1)° (Fig 1). In the crystal the molecules are connected by intermolecular H-bonds between the two independent molecules to form a dimer (Table 1, Fig. 2).