PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o453.
Published online 2010 January 27. doi:  10.1107/S160053681000259X
PMCID: PMC2979714

3-(Phenyl­imino)indolin-2-one

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0o453-scheme1.jpg

Experimental

Crystal data

  • C14H10N2O
  • M r = 222.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o453-efi1.jpg
  • a = 20.1647 (4) Å
  • b = 5.0223 (1) Å
  • c = 21.8791 (5) Å
  • V = 2215.77 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.3 × 0.3 × 0.3 mm

Data collection

  • Bruker APEXII diffractometer
  • 15055 measured reflections
  • 2619 independent reflections
  • 2042 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.118
  • S = 1.10
  • 2619 reflections
  • 315 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000259X/bt5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000259X/bt5177Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

C14H10N2OF(000) = 928
Mr = 222.24Dx = 1.332 Mg m3
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 mm1
c = 21.8791 (5) ÅT = 293 K
V = 2215.77 (8) Å3Block, orange
Z = 80.3 × 0.3 × 0.3 mm

Data collection

Bruker APEXII diffractometer2042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 27.5°, θmin = 1.9°
[var phi] and ω scansh = −24→26
15055 measured reflectionsk = −3→6
2619 independent reflectionsl = −28→28

Refinement

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 = 1.10w = 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 Å3
3 restraintsΔρmin = −0.20 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5177).

References

  • Akkurt, M., Öztürk, S., Erçağ, A., Özgür, M. Ü. & Heinemann, F. W. (2003). Acta Cryst. E59, o780–o782.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • 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. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography