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Acta Crystallogr Sect E Struct Rep Online. Oct 1, 2012; 68(Pt 10): o3030.
Published online Sep 29, 2012. doi:  10.1107/S1600536812040354
PMCID: PMC3470384
(E)-N-(3,3-Diphenyl­allyl­idene)-3-nitro­aniline
Joo Hwan Cha,a Yong Koo Kang,b Yong Seo Cho,b Jae Kyun Lee,b* and Jae Choon Wooc
aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
cDrug Discovery Platform Technology Team, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea
Correspondence e-mail: j9601/at/kist.re.kr
Received September 17, 2012; Accepted September 24, 2012.
Abstract
In the title compound, C21H16N2O2, the 3-nitro­phenyl and two phenyl rings are twisted from the mean plane of the enimino fragment by 44.4 (1), 37.2 (1) and 74.1 (1)°, respectively. The crystal packing exhibits no classical inter­molecular contacts.
Related literature  
For the structure of (E)-N-(3,3-diphenylallylidene)-4-nitroaniline, see: Kang et al. (2012 [triangle]). For the crystal structures of other closely related compounds, see: Khalaji et al. (2008a [triangle],b [triangle]).
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Object name is e-68-o3030-scheme1.jpg Object name is e-68-o3030-scheme1.jpg
Crystal data  
  • C21H16N2O2
  • M r = 328.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o3030-efi1.jpg
  • a = 5.8625 (7) Å
  • b = 22.825 (3) Å
  • c = 12.6370 (17) Å
  • β = 94.772 (4)°
  • V = 1685.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.40 × 0.20 × 0.20 mm
Data collection  
  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 [triangle]) T min = 0.967, T max = 0.983
  • 16270 measured reflections
  • 3866 independent reflections
  • 2663 reflections with I > 2σ(I)
  • R int = 0.030
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.136
  • S = 1.12
  • 3866 reflections
  • 226 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.25 e Å−3
Data collection: RAPID-AUTO (Rigaku, 2006 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: CrystalStructure (Rigaku, 2010 [triangle]); software used to prepare material for publication: CrystalStructure.
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040354/cv5343sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040354/cv5343Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812040354/cv5343Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.
supplementary crystallographic information
Comment
In the title molecule (Fig. 1), the dihedral angles between the mean planes of the central 3-nitrophenyl ring and phenyl rings C7–C12 and C1–C6 are 86.76 (8)° and 8.23 (3)°, respectively. The bond lengths and angles are unexceptional and correspond to those observed in the related compounds Khalaji et al. (2008a,b). The imine group displays a torsion angle C21–C16–N1–C15 of -45.19 (18)°. The nitro group is twisted at 1.1 (2)° from the attached benzene ring. The crystal packing exhibits no classical intermolecular contacts.
Experimental
To a solution of 3-nitroaniline (4.0 mmol) in ethanol (10 mL) was treated with equimolar quantities of substituted 2-phenylcinnamaldehydes. The mixture was refluxed for 5 h, and the progress of the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography to afford the title compound in 60% yield. Recrystallization from ethanol gave crystals suitable for X-ray analysis.
Refinement
All hydrogen atoms were positioned geometrically (C—H = 0.93 Å), and refined using a riding model, with Uiso(H) = 1.2 Ueq(C).
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoid.
Crystal data
C21H16N2O2F(000) = 688
Mr = 328.36Dx = 1.294 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 8104 reflections
a = 5.8625 (7) Åθ = 3.1–27.5°
b = 22.825 (3) ŵ = 0.08 mm1
c = 12.6370 (17) ÅT = 296 K
β = 94.772 (4)°Block, colourless
V = 1685.1 (4) Å30.40 × 0.20 × 0.20 mm
Z = 4
Data collection
Rigaku R-AXIS RAPID diffractometer3866 independent reflections
Radiation source: fine-focus sealed tube2663 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −7→7
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)k = −29→29
Tmin = 0.967, Tmax = 0.983l = −16→16
16270 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
3866 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.25 e Å3
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
O11.2806 (3)0.79532 (9)0.84554 (13)0.1205 (6)
O21.5869 (3)0.74640 (6)0.83527 (11)0.0942 (5)
N11.14274 (19)0.90554 (5)0.51096 (9)0.0464 (3)
N21.4414 (3)0.78014 (6)0.79813 (11)0.0690 (4)
C10.5605 (3)1.01496 (6)0.15119 (11)0.0525 (4)
H10.65621.00340.09990.063*
C20.3920 (3)1.05589 (7)0.12595 (13)0.0613 (4)
H20.37761.07240.05840.074*
C30.2448 (3)1.07259 (7)0.19989 (13)0.0573 (4)
H30.12921.09960.18200.069*
C40.2700 (2)1.04891 (6)0.30091 (12)0.0506 (3)
H40.17171.06020.35130.061*
C50.4406 (2)1.00859 (6)0.32705 (11)0.0452 (3)
H50.45670.99310.39530.054*
C60.5893 (2)0.99065 (5)0.25294 (10)0.0405 (3)
C71.0213 (2)0.90953 (7)0.14288 (12)0.0557 (4)
H71.13020.93760.16450.067*
C81.0584 (3)0.87204 (8)0.05913 (13)0.0639 (4)
H81.19130.87560.02430.077*
C90.9005 (3)0.82994 (7)0.02771 (12)0.0604 (4)
H90.92650.8050−0.02820.072*
C100.7044 (3)0.82455 (6)0.07869 (13)0.0594 (4)
H100.59790.79570.05800.071*
C110.6648 (2)0.86225 (6)0.16137 (11)0.0510 (3)
H110.53060.85870.19530.061*
C120.8224 (2)0.90501 (6)0.19400 (10)0.0410 (3)
C130.7721 (2)0.94683 (5)0.28026 (10)0.0398 (3)
C140.8838 (2)0.94559 (6)0.37731 (10)0.0442 (3)
H140.84890.97490.42450.053*
C151.0533 (2)0.90295 (6)0.41509 (10)0.0443 (3)
H151.09750.87370.36990.053*
C161.3099 (2)0.86430 (5)0.54794 (10)0.0410 (3)
C171.2973 (2)0.84251 (6)0.65043 (10)0.0463 (3)
H171.17830.85360.69040.056*
C181.4632 (2)0.80448 (6)0.69138 (11)0.0482 (3)
C191.6476 (2)0.78813 (6)0.63736 (13)0.0539 (4)
H191.75940.76300.66780.065*
C201.6606 (2)0.81029 (6)0.53643 (13)0.0554 (4)
H201.78350.80020.49810.067*
C211.4928 (2)0.84741 (6)0.49177 (11)0.0495 (3)
H211.50260.86130.42310.059*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.1312 (13)0.1592 (16)0.0769 (10)0.0438 (12)0.0438 (10)0.0502 (10)
O20.1215 (11)0.0826 (9)0.0741 (9)0.0176 (8)−0.0187 (8)0.0249 (7)
N10.0500 (6)0.0493 (6)0.0393 (6)0.0027 (5)0.0002 (5)0.0003 (5)
N20.0866 (10)0.0658 (9)0.0528 (8)0.0040 (7)−0.0050 (8)0.0130 (7)
C10.0609 (8)0.0564 (8)0.0408 (7)0.0120 (7)0.0083 (6)0.0034 (6)
C20.0769 (10)0.0594 (9)0.0473 (8)0.0162 (8)0.0031 (7)0.0086 (7)
C30.0589 (8)0.0508 (8)0.0614 (9)0.0128 (7)0.0000 (7)−0.0032 (7)
C40.0492 (7)0.0508 (8)0.0528 (8)0.0019 (6)0.0092 (6)−0.0097 (6)
C50.0489 (7)0.0467 (7)0.0402 (7)−0.0042 (6)0.0051 (6)−0.0033 (6)
C60.0439 (6)0.0399 (6)0.0375 (6)−0.0028 (5)0.0025 (5)−0.0023 (5)
C70.0442 (7)0.0690 (9)0.0536 (8)−0.0002 (7)0.0027 (6)−0.0100 (7)
C80.0522 (8)0.0849 (11)0.0549 (9)0.0185 (8)0.0053 (7)−0.0081 (8)
C90.0762 (10)0.0566 (9)0.0464 (8)0.0275 (8)−0.0068 (8)−0.0081 (7)
C100.0752 (10)0.0443 (8)0.0564 (9)0.0008 (7)−0.0073 (8)−0.0059 (6)
C110.0552 (8)0.0493 (8)0.0483 (8)−0.0040 (6)0.0020 (6)−0.0015 (6)
C120.0420 (6)0.0421 (7)0.0380 (7)0.0047 (5)−0.0019 (5)0.0020 (5)
C130.0409 (6)0.0403 (6)0.0386 (6)−0.0033 (5)0.0051 (5)0.0012 (5)
C140.0474 (7)0.0443 (7)0.0405 (7)−0.0004 (6)0.0010 (6)−0.0019 (5)
C150.0479 (7)0.0448 (7)0.0400 (7)−0.0032 (6)0.0020 (6)−0.0004 (5)
C160.0439 (6)0.0415 (6)0.0370 (6)−0.0037 (5)−0.0001 (5)−0.0026 (5)
C170.0477 (7)0.0519 (7)0.0395 (7)0.0006 (6)0.0053 (6)−0.0013 (6)
C180.0559 (7)0.0451 (7)0.0425 (7)−0.0035 (6)−0.0034 (6)0.0011 (6)
C190.0528 (8)0.0434 (7)0.0637 (9)0.0046 (6)−0.0056 (7)−0.0020 (6)
C200.0485 (7)0.0523 (8)0.0667 (10)0.0017 (7)0.0123 (7)−0.0082 (7)
C210.0544 (7)0.0502 (7)0.0450 (7)−0.0032 (6)0.0094 (6)−0.0004 (6)
Geometric parameters (Å, º)
O1—N21.209 (2)C9—C101.369 (2)
O2—N21.2144 (18)C9—H90.9300
N1—C151.2808 (16)C10—C111.388 (2)
N1—C161.4101 (16)C10—H100.9300
N2—C181.4742 (19)C11—C121.3831 (19)
C1—C21.378 (2)C11—H110.9300
C1—C61.3977 (18)C12—C131.4965 (18)
C1—H10.9300C13—C141.3419 (18)
C2—C31.378 (2)C14—C151.4435 (18)
C2—H20.9300C14—H140.9300
C3—C41.383 (2)C15—H150.9300
C3—H30.9300C16—C211.3890 (19)
C4—C51.3792 (19)C16—C171.3950 (18)
C4—H40.9300C17—C181.3722 (19)
C5—C61.3930 (18)C17—H170.9300
C5—H50.9300C18—C191.377 (2)
C6—C131.4852 (17)C19—C201.380 (2)
C7—C121.383 (2)C19—H190.9300
C7—C81.392 (2)C20—C211.383 (2)
C7—H70.9300C20—H200.9300
C8—C91.370 (2)C21—H210.9300
C8—H80.9300
C15—N1—C16120.07 (12)C12—C11—C10120.85 (14)
O1—N2—O2122.82 (15)C12—C11—H11119.6
O1—N2—C18118.43 (14)C10—C11—H11119.6
O2—N2—C18118.75 (16)C7—C12—C11118.79 (12)
C2—C1—C6120.77 (13)C7—C12—C13121.17 (12)
C2—C1—H1119.6C11—C12—C13119.99 (11)
C6—C1—H1119.6C14—C13—C6120.97 (12)
C3—C2—C1120.55 (14)C14—C13—C12122.78 (11)
C3—C2—H2119.7C6—C13—C12116.25 (10)
C1—C2—H2119.7C13—C14—C15125.94 (12)
C2—C3—C4119.55 (13)C13—C14—H14117.0
C2—C3—H3120.2C15—C14—H14117.0
C4—C3—H3120.2N1—C15—C14119.87 (13)
C5—C4—C3120.11 (13)N1—C15—H15120.1
C5—C4—H4119.9C14—C15—H15120.1
C3—C4—H4119.9C21—C16—C17118.56 (12)
C4—C5—C6121.14 (13)C21—C16—N1124.11 (12)
C4—C5—H5119.4C17—C16—N1117.18 (12)
C6—C5—H5119.4C18—C17—C16119.03 (13)
C5—C6—C1117.87 (12)C18—C17—H17120.5
C5—C6—C13121.42 (12)C16—C17—H17120.5
C1—C6—C13120.71 (12)C17—C18—C19123.04 (13)
C12—C7—C8120.03 (14)C17—C18—N2118.09 (14)
C12—C7—H7120.0C19—C18—N2118.87 (13)
C8—C7—H7120.0C18—C19—C20117.71 (13)
C9—C8—C7120.46 (15)C18—C19—H19121.1
C9—C8—H8119.8C20—C19—H19121.1
C7—C8—H8119.8C21—C20—C19120.63 (14)
C10—C9—C8120.01 (14)C21—C20—H20119.7
C10—C9—H9120.0C19—C20—H20119.7
C8—C9—H9120.0C20—C21—C16120.99 (13)
C9—C10—C11119.85 (14)C20—C21—H21119.5
C9—C10—H10120.1C16—C21—H21119.5
C11—C10—H10120.1
C6—C1—C2—C3−1.6 (2)C7—C12—C13—C6107.60 (13)
C1—C2—C3—C41.4 (2)C11—C12—C13—C6−69.96 (15)
C2—C3—C4—C5−0.4 (2)C6—C13—C14—C15175.77 (12)
C3—C4—C5—C6−0.4 (2)C12—C13—C14—C15−4.3 (2)
C4—C5—C6—C10.18 (18)C16—N1—C15—C14−179.44 (11)
C4—C5—C6—C13−179.42 (11)C13—C14—C15—N1−177.81 (13)
C2—C1—C6—C50.8 (2)C15—N1—C16—C2145.24 (18)
C2—C1—C6—C13−179.58 (13)C15—N1—C16—C17−139.32 (13)
C12—C7—C8—C9−1.0 (2)C21—C16—C17—C18−1.14 (18)
C7—C8—C9—C100.1 (2)N1—C16—C17—C18−176.83 (11)
C8—C9—C10—C110.7 (2)C16—C17—C18—C192.3 (2)
C9—C10—C11—C12−0.7 (2)C16—C17—C18—N2−177.55 (12)
C8—C7—C12—C111.0 (2)O1—N2—C18—C17−1.1 (2)
C8—C7—C12—C13−176.60 (13)O2—N2—C18—C17179.95 (14)
C10—C11—C12—C7−0.2 (2)O1—N2—C18—C19179.04 (17)
C10—C11—C12—C13177.46 (12)O2—N2—C18—C190.1 (2)
C5—C6—C13—C14−36.10 (17)C17—C18—C19—C20−1.6 (2)
C1—C6—C13—C14144.31 (14)N2—C18—C19—C20178.26 (12)
C5—C6—C13—C12143.96 (12)C18—C19—C20—C21−0.3 (2)
C1—C6—C13—C12−35.63 (16)C19—C20—C21—C161.4 (2)
C7—C12—C13—C14−72.33 (17)C17—C16—C21—C20−0.66 (19)
C11—C12—C13—C14110.11 (14)N1—C16—C21—C20174.72 (11)
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5343).
References
  • Kang, Y. K., Cho, Y. S., Lee, J. K., Yu, B.-Y. & Cha, J. H. (2012). Acta Cryst. E68, o3031. [PMC free article] [PubMed]
  • Khalaji, A. D. & Harrison, W. T. A. (2008a). Anal. Sci. X-Ray Struct. Anal. Online, 24, x3–x4.
  • Khalaji, A. D., Welter, R., Amirnasr, M. & Barry, A. H. (2008b). Anal. Sci. X-Ray Struct. Anal. Online, 24, x139–x140.
  • Rigaku (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2006). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2010). CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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