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Acta Cryst. (2010). E66, o453    [ doi:10.1107/S160053681000259X ]

3-(Phenylimino)indolin-2-one

A. Al Subari, R. Bouhfid, H. Zouihri, E. M. Essassi and S. W. Ng

Abstract top

The imino C=N double bond in the title compound, C14H10N2O, exists in an E conformation, with the phenyl ring being twisted by 80.7 (1)° in one independent molecule and by 81.4 (1)° in the other with respect to the plane of the indoline fused-ring system. The two independent molecules are linked by N-H...O hydrogen bonds, forming a zigzag chain running along the a axis.

Related literature top

For the synthesis, see: Grimshaw & Begley (1974). For the crystal structures of other phenyl-substituted derivatives, see: Akkurt et al. (2003); Hökelek et al. (2006); Öztürk et al. (2003).

Experimental top

The compound was synthesized from the reaction of isatin and aniline in ethanol according to a literature method (Grimshaw & Begley, 1974), and crystals were obtained by recrystallization from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N–H 0.86±0.01 Å. Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C14H10N2O at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.
3-(Phenylimino)indolin-2-one top
Crystal data top
C14H10N2OF(000) = 928
Mr = 222.24Dx = 1.332 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3521 reflections
a = 20.1647 (4) Åθ = 2.7–25.7°
b = 5.0223 (1) ŵ = 0.09 mm−1
c = 21.8791 (5) ÅT = 293 K
V = 2215.77 (8) Å3Block, orange
Z = 80.3 × 0.3 × 0.3 mm
Data collection top
Bruker APEXII
diffractometer		2042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 27.5°, θmin = 1.9°
φ and ω scansh = −24→26
15055 measured reflectionsk = −3→6
2619 independent reflectionsl = −28→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0745P)2 + 0.0171P]
where P = (Fo2 + 2Fc2)/3
2619 reflections(Δ/σ)max = 0.001
315 parametersΔρmax = 0.19 e Å−3
3 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C14H10N2OV = 2215.77 (8) Å3
Mr = 222.24Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 20.1647 (4) ŵ = 0.09 mm−1
b = 5.0223 (1) ÅT = 293 K
c = 21.8791 (5) Å0.3 × 0.3 × 0.3 mm
Data collection top
Bruker APEXII
diffractometer		Rint = 0.030
15055 measured reflectionsθmax = 27.5°
2619 independent reflectionsStandard reflections: 0
2042 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118Δρmax = 0.19 e Å−3
S = 1.10Δρmin = −0.20 e Å−3
2619 reflectionsAbsolute structure: ?
315 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.36628 (12)0.9072 (6)0.49888 (10)0.0769 (7)
O20.11993 (12)0.6636 (6)0.52675 (12)0.0816 (8)
N10.44843 (11)0.6264 (6)0.53285 (11)0.0543 (6)
N20.28865 (11)0.6607 (5)0.59271 (10)0.0505 (6)
N30.20427 (11)0.9352 (5)0.49173 (10)0.0535 (6)
N40.04413 (11)0.9133 (5)0.43186 (11)0.0525 (6)
C10.38742 (14)0.7371 (6)0.53269 (13)0.0535 (7)
C20.34907 (12)0.5996 (5)0.58405 (11)0.0462 (6)
C30.39537 (12)0.4079 (5)0.61115 (11)0.0446 (6)
C40.39058 (14)0.2185 (6)0.65685 (13)0.0519 (7)
H40.35170.20140.67940.062*
C50.44415 (16)0.0553 (6)0.66857 (15)0.0605 (7)
H50.4414−0.07240.69930.073*
C60.50158 (16)0.0802 (7)0.63515 (17)0.0663 (8)
H60.5370−0.03270.64360.080*
C70.50835 (15)0.2678 (7)0.58932 (15)0.0609 (8)
H70.54750.28400.56720.073*
C80.45450 (13)0.4302 (6)0.57769 (12)0.0481 (6)
C90.25376 (12)0.5309 (5)0.64115 (12)0.0454 (6)
C100.20928 (13)0.3331 (7)0.62764 (14)0.0565 (7)
H100.20170.28500.58720.068*
C110.17563 (15)0.2051 (7)0.67433 (17)0.0619 (8)
H110.14640.06730.66530.074*
C120.18528 (14)0.2810 (7)0.73385 (15)0.0594 (8)
H120.16280.19380.76510.071*
C130.22774 (15)0.4843 (6)0.74728 (13)0.0565 (7)
H130.23340.53810.78760.068*
C140.26251 (16)0.6108 (6)0.70102 (13)0.0536 (7)
H140.29160.74880.71020.064*
C150.14226 (13)0.8292 (7)0.49218 (13)0.0539 (7)
C160.10494 (12)0.9666 (5)0.44047 (11)0.0455 (6)
C170.15210 (13)1.1524 (5)0.41286 (11)0.0437 (6)
C180.14711 (14)1.3414 (6)0.36677 (13)0.0528 (7)
H180.10801.35960.34470.063*
C190.20099 (16)1.5019 (6)0.35414 (15)0.0609 (7)
H190.19831.62950.32350.073*
C200.25942 (17)1.4720 (7)0.38751 (17)0.0661 (8)
H200.29551.58030.37850.079*
C210.26500 (16)1.2858 (7)0.43355 (16)0.0620 (8)
H210.30421.26790.45550.074*
C220.21093 (13)1.1269 (5)0.44624 (12)0.0472 (6)
C230.00927 (12)1.0342 (6)0.38269 (12)0.0461 (6)
C240.01763 (15)0.9423 (6)0.32334 (14)0.0576 (7)
H240.04780.80650.31540.069*
C25−0.01848 (16)1.0510 (7)0.27619 (16)0.0610 (8)
H25−0.01260.98870.23650.073*
C26−0.06293 (15)1.2504 (7)0.28746 (16)0.0630 (8)
H26−0.08691.32550.25550.076*
C27−0.07213 (15)1.3401 (7)0.34652 (17)0.0687 (9)
H27−0.10251.47550.35410.082*
C28−0.03689 (14)1.2315 (7)0.39430 (14)0.0586 (7)
H28−0.04411.29030.43410.070*
H10.4791 (10)0.653 (6)0.5061 (10)0.052 (8)*
H30.2338 (12)0.883 (7)0.5172 (12)0.064 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0687 (14)0.0941 (18)0.0678 (15)0.0084 (12)0.0068 (11)0.0340 (13)
O20.0684 (14)0.104 (2)0.0721 (14)−0.0040 (13)−0.0001 (12)0.0422 (15)
N10.0457 (13)0.0711 (16)0.0461 (12)−0.0002 (11)0.0104 (10)0.0017 (12)
N20.0423 (12)0.0625 (15)0.0468 (12)0.0047 (10)0.0007 (9)0.0070 (11)
N30.0483 (12)0.0653 (15)0.0470 (12)0.0081 (11)−0.0064 (10)0.0028 (11)
N40.0419 (12)0.0659 (15)0.0498 (12)0.0040 (11)0.0037 (9)0.0097 (11)
C10.0477 (15)0.0673 (19)0.0454 (15)−0.0002 (13)0.0020 (12)0.0021 (14)
C20.0440 (13)0.0533 (15)0.0414 (12)−0.0015 (11)−0.0017 (10)−0.0023 (12)
C30.0424 (13)0.0466 (14)0.0447 (13)0.0000 (11)−0.0018 (10)−0.0070 (11)
C40.0528 (15)0.0507 (15)0.0523 (16)−0.0015 (12)−0.0007 (12)−0.0013 (13)
C50.0673 (18)0.0514 (16)0.0628 (17)0.0045 (14)−0.0089 (15)0.0015 (14)
C60.0586 (17)0.0610 (18)0.079 (2)0.0137 (15)−0.0129 (15)−0.0068 (17)
C70.0498 (16)0.0683 (19)0.0645 (19)0.0081 (13)0.0051 (14)−0.0094 (16)
C80.0452 (14)0.0521 (15)0.0471 (13)0.0008 (11)0.0006 (11)−0.0098 (12)
C90.0355 (12)0.0527 (15)0.0479 (13)0.0082 (11)0.0022 (10)0.0033 (12)
C100.0534 (16)0.0620 (18)0.0541 (16)−0.0013 (14)−0.0060 (14)−0.0022 (14)
C110.0501 (16)0.0592 (17)0.076 (2)−0.0087 (14)−0.0041 (15)0.0083 (16)
C120.0505 (17)0.0612 (18)0.067 (2)0.0046 (14)0.0100 (14)0.0159 (15)
C130.0664 (17)0.0566 (16)0.0465 (14)0.0090 (14)0.0075 (13)−0.0021 (13)
C140.0539 (16)0.0525 (16)0.0544 (16)−0.0026 (13)0.0024 (12)−0.0016 (12)
C150.0486 (15)0.0687 (19)0.0444 (15)0.0099 (14)0.0045 (12)0.0066 (13)
C160.0411 (13)0.0532 (15)0.0422 (13)0.0076 (11)0.0045 (10)0.0025 (11)
C170.0444 (14)0.0452 (14)0.0414 (13)0.0083 (11)0.0055 (10)−0.0025 (10)
C180.0525 (16)0.0513 (15)0.0545 (17)0.0073 (12)0.0051 (13)0.0036 (13)
C190.0660 (18)0.0527 (16)0.0640 (17)0.0002 (14)0.0109 (15)0.0083 (15)
C200.0609 (17)0.0572 (18)0.080 (2)−0.0122 (15)0.0092 (17)−0.0001 (17)
C210.0492 (16)0.0621 (18)0.075 (2)−0.0016 (13)−0.0026 (15)−0.0090 (17)
C220.0468 (14)0.0480 (14)0.0467 (13)0.0062 (11)0.0026 (11)−0.0062 (12)
C230.0355 (12)0.0510 (15)0.0519 (14)0.0011 (11)0.0023 (10)0.0069 (12)
C240.0606 (17)0.0549 (17)0.0572 (16)0.0146 (13)0.0025 (14)0.0000 (14)
C250.0688 (19)0.0606 (18)0.0536 (15)0.0011 (15)−0.0094 (14)−0.0036 (15)
C260.0542 (18)0.0700 (19)0.065 (2)0.0061 (15)−0.0105 (14)0.0155 (16)
C270.0550 (18)0.069 (2)0.082 (2)0.0236 (15)0.0052 (16)0.0144 (18)
C280.0542 (16)0.0647 (19)0.0569 (17)0.0108 (14)0.0077 (14)0.0011 (14)
Geometric parameters (Å, °) top
O1—C11.208 (4)C11—H110.9300
O2—C151.211 (4)C12—C131.364 (5)
N1—C11.350 (4)C12—H120.9300
N1—C81.396 (4)C13—C141.386 (4)
N1—H10.86 (1)C13—H130.9300
N2—C21.271 (3)C14—H140.9300
N2—C91.429 (3)C15—C161.524 (4)
N3—C151.359 (4)C16—C171.463 (4)
N3—C221.391 (4)C17—C181.389 (4)
N3—H30.86 (1)C17—C221.399 (4)
N4—C161.269 (3)C18—C191.381 (4)
N4—C231.421 (3)C18—H180.9300
C1—C21.529 (4)C19—C201.394 (5)
C2—C31.466 (4)C19—H190.9300
C3—C41.383 (4)C20—C211.379 (5)
C3—C81.404 (4)C20—H200.9300
C4—C51.380 (4)C21—C221.380 (4)
C4—H40.9300C21—H210.9300
C5—C61.375 (5)C23—C281.383 (4)
C5—H50.9300C23—C241.389 (4)
C6—C71.383 (5)C24—C251.376 (4)
C6—H60.9300C24—H240.9300
C7—C81.382 (4)C25—C261.366 (4)
C7—H70.9300C25—H250.9300
C9—C101.371 (4)C26—C271.381 (5)
C9—C141.381 (4)C26—H260.9300
C10—C111.385 (4)C27—C281.377 (4)
C10—H100.9300C27—H270.9300
C11—C121.371 (5)C28—H280.9300
C1—N1—C8111.9 (2)C14—C13—H13119.9
C1—N1—H1126 (2)C9—C14—C13119.7 (3)
C8—N1—H1121 (2)C9—C14—H14120.2
C2—N2—C9118.2 (2)C13—C14—H14120.2
C15—N3—C22111.4 (2)O2—C15—N3128.0 (3)
C15—N3—H3121 (2)O2—C15—C16126.2 (3)
C22—N3—H3128 (2)N3—C15—C16105.7 (2)
C16—N4—C23120.0 (2)N4—C16—C17134.5 (2)
O1—C1—N1127.9 (3)N4—C16—C15119.4 (2)
O1—C1—C2126.2 (3)C17—C16—C15105.9 (2)
N1—C1—C2105.8 (2)C18—C17—C22120.2 (3)
N2—C2—C3135.1 (3)C18—C17—C16133.5 (3)
N2—C2—C1119.0 (2)C22—C17—C16106.1 (2)
C3—C2—C1105.8 (2)C19—C18—C17119.2 (3)
C4—C3—C8119.4 (3)C19—C18—H18120.4
C4—C3—C2134.4 (2)C17—C18—H18120.4
C8—C3—C2106.1 (2)C18—C19—C20119.8 (3)
C5—C4—C3119.2 (3)C18—C19—H19120.1
C5—C4—H4120.4C20—C19—H19120.1
C3—C4—H4120.4C21—C20—C19121.6 (3)
C6—C5—C4120.4 (3)C21—C20—H20119.2
C6—C5—H5119.8C19—C20—H20119.2
C4—C5—H5119.8C20—C21—C22118.3 (3)
C5—C6—C7122.0 (3)C20—C21—H21120.8
C5—C6—H6119.0C22—C21—H21120.8
C7—C6—H6119.0C21—C22—N3128.4 (3)
C8—C7—C6117.3 (3)C21—C22—C17120.8 (3)
C8—C7—H7121.4N3—C22—C17110.8 (2)
C6—C7—H7121.4C28—C23—C24119.5 (3)
C7—C8—N1128.0 (3)C28—C23—N4120.0 (3)
C7—C8—C3121.6 (3)C24—C23—N4120.4 (3)
N1—C8—C3110.4 (2)C25—C24—C23120.3 (3)
C10—C9—C14119.9 (3)C25—C24—H24119.8
C10—C9—N2119.5 (3)C23—C24—H24119.8
C14—C9—N2120.5 (3)C26—C25—C24120.2 (3)
C9—C10—C11119.9 (3)C26—C25—H25119.9
C9—C10—H10120.1C24—C25—H25119.9
C11—C10—H10120.1C25—C26—C27119.7 (3)
C12—C11—C10120.1 (3)C25—C26—H26120.1
C12—C11—H11119.9C27—C26—H26120.1
C10—C11—H11119.9C28—C27—C26120.8 (3)
C13—C12—C11120.1 (3)C28—C27—H27119.6
C13—C12—H12119.9C26—C27—H27119.6
C11—C12—H12119.9C27—C28—C23119.5 (3)
C12—C13—C14120.2 (3)C27—C28—H28120.3
C12—C13—H13119.9C23—C28—H28120.3
C8—N1—C1—O1−178.4 (3)C22—N3—C15—O2−178.1 (3)
C8—N1—C1—C20.7 (3)C22—N3—C15—C160.7 (3)
C9—N2—C2—C33.4 (5)C23—N4—C16—C175.7 (5)
C9—N2—C2—C1−179.7 (2)C23—N4—C16—C15−178.2 (2)
O1—C1—C2—N21.5 (5)O2—C15—C16—N41.7 (5)
N1—C1—C2—N2−177.6 (3)N3—C15—C16—N4−177.1 (3)
O1—C1—C2—C3179.3 (3)O2—C15—C16—C17178.9 (3)
N1—C1—C2—C30.1 (3)N3—C15—C16—C170.1 (3)
N2—C2—C3—C40.2 (6)N4—C16—C17—C180.4 (5)
C1—C2—C3—C4−177.1 (3)C15—C16—C17—C18−176.1 (3)
N2—C2—C3—C8176.3 (3)N4—C16—C17—C22175.8 (3)
C1—C2—C3—C8−0.9 (3)C15—C16—C17—C22−0.8 (3)
C8—C3—C4—C50.0 (4)C22—C17—C18—C190.4 (4)
C2—C3—C4—C5175.7 (3)C16—C17—C18—C19175.2 (3)
C3—C4—C5—C6−0.1 (4)C17—C18—C19—C200.1 (4)
C4—C5—C6—C70.4 (5)C18—C19—C20—C21−0.4 (5)
C5—C6—C7—C8−0.6 (5)C19—C20—C21—C220.0 (5)
C6—C7—C8—N1−177.6 (3)C20—C21—C22—N3−177.2 (3)
C6—C7—C8—C30.4 (4)C20—C21—C22—C170.6 (4)
C1—N1—C8—C7176.8 (3)C15—N3—C22—C21176.7 (3)
C1—N1—C8—C3−1.4 (3)C15—N3—C22—C17−1.2 (3)
C4—C3—C8—C7−0.1 (4)C18—C17—C22—C21−0.8 (4)
C2—C3—C8—C7−177.0 (3)C16—C17—C22—C21−176.9 (2)
C4—C3—C8—N1178.2 (2)C18—C17—C22—N3177.3 (2)
C2—C3—C8—N11.4 (3)C16—C17—C22—N31.2 (3)
C2—N2—C9—C10−104.2 (3)C16—N4—C23—C28−107.2 (3)
C2—N2—C9—C1478.5 (4)C16—N4—C23—C2477.5 (4)
C14—C9—C10—C11−3.1 (4)C28—C23—C24—C251.6 (5)
N2—C9—C10—C11179.5 (2)N4—C23—C24—C25176.9 (3)
C9—C10—C11—C121.9 (4)C23—C24—C25—C26−0.1 (5)
C10—C11—C12—C130.5 (5)C24—C25—C26—C27−0.9 (5)
C11—C12—C13—C14−1.5 (5)C25—C26—C27—C280.2 (5)
C10—C9—C14—C132.1 (4)C26—C27—C28—C231.4 (5)
N2—C9—C14—C13179.4 (2)C24—C23—C28—C27−2.3 (5)
C12—C13—C14—C90.3 (4)N4—C23—C28—C27−177.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.86 (3)2.11 (2)2.940 (3)161 (3)
N3—H3···N20.86 (3)2.28 (3)3.111 (3)164 (3)
Symmetry codes: (i) x+1/2, −y+3/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.86 (3)2.11 (2)2.940 (3)161 (3)
N3—H3···N20.86 (3)2.28 (3)3.111 (3)164 (3)
Symmetry codes: (i) x+1/2, −y+3/2, z.
Acknowledgements top

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

references
References top

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Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Grimshaw, J. & Begley, W. J. (1974). Synthesis, pp. 496–498.

Hökelek, T., Erçag, A., Çoruh, U., Vazquez-Lopez, E. M. & Özgür, M. Ü. (2006). Anal. Sci. X-Ray Struct. Anal. Online, 21, x129–x130.

Öztürk, S., Akkurt, M., Özgür, M. Ü., Erçağ, A. & Heinemann, F. W. (2003). Acta Cryst. E59, o569–o571.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). publCIF. In preparation.