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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1810.
Published online 2009 July 11. doi:  10.1107/S1600536809026087
PMCID: PMC2977415

1,2-Diphenyl-2-[4-(4-pyridyl)benzyl­idene­hydrazono]ethan-1-one

Abstract

In the title compound, C26H19N3O, the dimethyl­ene hydrazine (—C=N—N=C—) unit is approximately planar, the torsion angle around the N—N bond being 162.2 (6)°. The phenyl and benzoyl­phenyl rings at one end of the hydrazine unit are aligned at angles of 9.5 (5) and 88.5 (4)°, respectively, with respect to the hydrazine unit, whereas the benzene ring at the other end is twisted by an angle of 14.4 (4)°. In the crystal structure, mol­ecules are linked into centrosymmetric dimers by inter­molecular C—H(...)O hydrogen bonds. The monoclinic crystal under investigation shows pseudo-merohedral twinning with twin fractions of 0.63 and 0.37.

Related literature

For the crystal structures of other carbaldehyde N′-benzoyl-N′-phenyl­hydrazones, see: Abbasi et al. (2007 [triangle]); Chowdhury et al. (2003 [triangle]); Liu et al. (2007 [triangle]); Schweizer et al. (1987 [triangle]).

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Object name is e-65-o1810-scheme1.jpg

Experimental

Crystal data

  • C26H19N3O
  • M r = 389.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1810-efi1.jpg
  • a = 7.1182 (2) Å
  • b = 23.2745 (7) Å
  • c = 11.8040 (4) Å
  • β = 90.278 (2)°
  • V = 1955.6 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 140 K
  • 0.45 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: none
  • 11057 measured reflections
  • 3433 independent reflections
  • 2825 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.093
  • wR(F 2) = 0.252
  • S = 1.08
  • 3433 reflections
  • 260 parameters
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026087/ci2837sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026087/ci2837Isup2.hkl

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

Acknowledgments

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Benzil monohydrazone (0.224 g, 1 mmol) was dissolved in methanol (20 ml) and to this was added 4-pyridylbenzaldehyde (0.183 g, 1 mmol). The resulting yellowish mixture was heated for 6 h. The solvent was evaporated and the solid was recrystallized from methanol in 80% yield; m.p. 461 K.

Refinement

H atoms were placed in calculated positions (C-H = 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The aromatic ring of the benzoyl unit was refined as a rigid hexagon (C—C = 1.39 Å); attempts to refine the ring as two overlapping rings were unsuccessful. The monoclinic unit cell emulates an orthorhombic unit cell; the use of the twin law (-100 010 001) showed twin fractions are in the ratio 0.63:0.37.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C26H19N3O at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

Crystal data

C26H19N3OF(000) = 816
Mr = 389.44Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2404 reflections
a = 7.1182 (2) Åθ = 2.5–23.3°
b = 23.2745 (7) ŵ = 0.08 mm1
c = 11.8040 (4) ÅT = 140 K
β = 90.278 (2)°Prism, brown
V = 1955.6 (1) Å30.45 × 0.15 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX area-detector diffractometer2825 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 25.0°, θmin = 0.9°
ω scansh = −8→8
11057 measured reflectionsk = −27→27
3433 independent reflectionsl = −13→14

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)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.252H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1142P)2 + 4.6222P] where P = (Fo2 + 2Fc2)/3
3433 reflections(Δ/σ)max = 0.001
260 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = −0.38 e Å3

Special details

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.

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

xyzUiso*/Ueq
O10.5484 (6)0.38713 (17)0.8664 (3)0.0404 (10)
N10.2040 (9)0.37367 (17)0.7012 (4)0.0419 (13)
N20.2387 (8)0.43390 (17)0.6961 (3)0.0343 (11)
N30.2956 (9)0.8061 (2)0.3966 (4)0.0487 (15)
C10.2861 (6)0.41267 (14)0.9747 (2)0.0366 (15)
C20.3933 (5)0.4384 (2)1.0593 (3)0.0541 (18)
H20.52660.43741.05540.065*
C30.3056 (6)0.46560 (18)1.1495 (3)0.0542 (18)
H30.37890.48321.20740.065*
C40.1107 (6)0.46707 (17)1.1552 (3)0.0477 (17)
H40.05070.48571.21690.057*
C50.0034 (5)0.4413 (2)1.0705 (4)0.0566 (19)
H5−0.12980.44241.07440.068*
C60.0911 (5)0.41414 (17)0.9803 (3)0.0427 (15)
H60.01780.39660.92240.051*
C70.3789 (9)0.3850 (2)0.8787 (4)0.0323 (13)
C80.2589 (8)0.3512 (2)0.7921 (4)0.0276 (11)
C90.2362 (8)0.2882 (2)0.8099 (4)0.0263 (11)
C100.1549 (8)0.2553 (2)0.7251 (5)0.0346 (13)
H100.10650.27330.65890.041*
C110.1442 (9)0.1956 (2)0.7373 (5)0.0386 (14)
H110.09160.17260.67870.046*
C120.2116 (10)0.1704 (2)0.8361 (5)0.0387 (14)
H120.21020.12980.84350.046*
C130.2799 (9)0.2034 (2)0.9232 (5)0.0379 (14)
H130.31640.18590.99250.045*
C140.2956 (9)0.2619 (2)0.9104 (4)0.0366 (14)
H140.34700.28450.97000.044*
C150.2301 (10)0.4523 (2)0.5948 (4)0.0415 (16)
H150.20820.42520.53600.050*
C160.2517 (9)0.5124 (2)0.5636 (4)0.0350 (13)
C170.2450 (11)0.5271 (2)0.4494 (4)0.0472 (18)
H170.23660.49780.39370.057*
C180.2504 (10)0.5839 (2)0.4160 (4)0.0380 (14)
H180.24820.59310.33770.046*
C190.2593 (8)0.62806 (19)0.4964 (4)0.0250 (11)
C200.2708 (9)0.6123 (2)0.6106 (4)0.0309 (12)
H200.28210.64160.66650.037*
C210.2661 (9)0.5562 (2)0.6441 (4)0.0328 (13)
H210.27270.54690.72240.039*
C220.2679 (8)0.6892 (2)0.4604 (4)0.0268 (11)
C230.2038 (10)0.7331 (2)0.5287 (5)0.0394 (15)
H230.14550.72450.59900.047*
C240.2249 (10)0.7896 (2)0.4943 (6)0.0478 (16)
H240.18520.81880.54510.057*
C250.3562 (10)0.7637 (2)0.3315 (5)0.0415 (15)
H250.41180.77380.26130.050*
C260.3452 (9)0.7060 (2)0.3573 (5)0.0365 (13)
H260.38980.67800.30540.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.043 (3)0.040 (2)0.038 (2)−0.0029 (19)0.004 (2)−0.0039 (18)
N10.079 (4)0.018 (2)0.029 (2)−0.004 (2)0.003 (3)−0.0024 (18)
N20.058 (3)0.0164 (19)0.028 (2)−0.002 (2)−0.005 (2)−0.0011 (16)
N30.071 (4)0.030 (2)0.045 (3)−0.003 (3)−0.005 (3)0.007 (2)
C10.073 (5)0.012 (2)0.024 (2)0.009 (3)−0.003 (3)0.0020 (18)
C20.054 (4)0.074 (5)0.035 (4)0.005 (4)0.000 (3)−0.018 (3)
C30.084 (6)0.053 (4)0.026 (3)−0.004 (4)−0.001 (3)−0.019 (3)
C40.073 (5)0.038 (3)0.033 (3)0.008 (3)0.006 (3)0.000 (3)
C50.058 (5)0.069 (5)0.042 (4)0.000 (4)−0.002 (3)−0.013 (3)
C60.047 (4)0.040 (3)0.041 (3)0.002 (3)0.000 (3)−0.012 (3)
C70.052 (4)0.019 (2)0.026 (3)0.000 (2)0.001 (3)0.008 (2)
C80.040 (3)0.024 (2)0.019 (2)0.006 (2)−0.001 (2)−0.0001 (19)
C90.032 (3)0.022 (2)0.025 (2)0.003 (2)−0.002 (2)−0.0011 (18)
C100.047 (4)0.032 (3)0.026 (3)0.001 (3)−0.001 (3)0.006 (2)
C110.054 (4)0.029 (3)0.032 (3)−0.006 (3)0.000 (3)−0.009 (2)
C120.060 (4)0.018 (2)0.038 (3)−0.009 (3)0.007 (3)0.003 (2)
C130.054 (4)0.032 (3)0.028 (3)−0.004 (3)−0.002 (3)0.000 (2)
C140.048 (4)0.037 (3)0.026 (3)−0.006 (3)0.002 (3)−0.002 (2)
C150.084 (5)0.018 (2)0.022 (3)0.007 (3)0.005 (3)−0.0030 (19)
C160.060 (4)0.023 (2)0.022 (2)0.007 (3)0.004 (3)0.0016 (19)
C170.100 (6)0.022 (3)0.020 (2)0.003 (3)0.006 (3)−0.005 (2)
C180.070 (4)0.023 (2)0.021 (2)0.009 (3)−0.001 (3)−0.0002 (19)
C190.032 (3)0.018 (2)0.026 (2)0.005 (2)0.002 (2)−0.0038 (18)
C200.047 (4)0.022 (2)0.025 (2)−0.004 (2)0.004 (3)−0.0036 (19)
C210.052 (4)0.031 (3)0.015 (2)0.002 (3)−0.005 (3)0.0019 (19)
C220.030 (3)0.025 (2)0.025 (2)0.001 (2)−0.004 (2)0.0019 (18)
C230.058 (4)0.030 (3)0.029 (3)0.008 (3)0.009 (3)0.000 (2)
C240.061 (4)0.031 (3)0.051 (4)0.001 (3)0.002 (4)−0.011 (3)
C250.055 (4)0.033 (3)0.037 (3)0.000 (3)0.011 (3)0.007 (2)
C260.043 (3)0.035 (3)0.031 (3)0.003 (3)0.007 (3)0.005 (2)

Geometric parameters (Å, °)

O1—C71.217 (7)C12—C131.370 (8)
N1—C81.255 (7)C12—H120.95
N1—N21.425 (6)C13—C141.374 (8)
N2—C151.271 (7)C13—H130.95
N3—C241.318 (8)C14—H140.95
N3—C251.325 (8)C15—C161.455 (7)
C1—C21.39C15—H150.95
C1—C61.39C16—C211.397 (7)
C1—C71.463 (6)C16—C171.392 (7)
C2—C31.39C17—C181.378 (7)
C2—H20.95C17—H170.95
C3—C41.39C18—C191.400 (7)
C3—H30.95C18—H180.95
C4—C51.39C19—C201.399 (7)
C4—H40.95C19—C221.487 (6)
C5—C61.39C20—C211.366 (7)
C5—H50.95C20—H200.95
C6—H60.95C21—H210.95
C7—C81.544 (8)C22—C231.379 (7)
C8—C91.490 (7)C22—C261.394 (7)
C9—C101.384 (7)C23—C241.387 (8)
C9—C141.399 (7)C23—H230.95
C10—C111.399 (8)C24—H240.95
C10—H100.95C25—C261.378 (8)
C11—C121.389 (8)C25—H250.95
C11—H110.95C26—H260.95
C8—N1—N2113.1 (4)C14—C13—H13119.9
C15—N2—N1111.3 (4)C13—C14—C9120.1 (5)
C24—N3—C25114.6 (5)C13—C14—H14119.9
C2—C1—C6120.0C9—C14—H14119.9
C2—C1—C7119.8 (4)N2—C15—C16123.8 (5)
C6—C1—C7120.1 (4)N2—C15—H15118.1
C1—C2—C3120.0C16—C15—H15118.1
C1—C2—H2120.0C21—C16—C17118.7 (4)
C3—C2—H2120.0C21—C16—C15122.5 (4)
C4—C3—C2120.0C17—C16—C15118.7 (5)
C4—C3—H3120.0C18—C17—C16120.8 (5)
C2—C3—H3120.0C18—C17—H17119.6
C5—C4—C3120.0C16—C17—H17119.6
C5—C4—H4120.0C17—C18—C19120.8 (5)
C3—C4—H4120.0C17—C18—H18119.6
C4—C5—C6120.0C19—C18—H18119.6
C4—C5—H5120.0C20—C19—C18117.6 (4)
C6—C5—H5120.0C20—C19—C22121.5 (4)
C5—C6—C1120.0C18—C19—C22120.8 (4)
C5—C6—H6120.0C21—C20—C19121.8 (4)
C1—C6—H6120.0C21—C20—H20119.1
O1—C7—C1121.7 (5)C19—C20—H20119.1
O1—C7—C8119.2 (5)C20—C21—C16120.2 (4)
C1—C7—C8119.1 (5)C20—C21—H21119.9
N1—C8—C9119.8 (4)C16—C21—H21119.9
N1—C8—C7121.5 (4)C23—C22—C26115.9 (5)
C9—C8—C7117.9 (4)C23—C22—C19121.8 (4)
C10—C9—C14119.7 (5)C26—C22—C19122.3 (5)
C10—C9—C8119.2 (4)C22—C23—C24119.6 (5)
C14—C9—C8121.1 (5)C22—C23—H23120.2
C11—C10—C9119.8 (5)C24—C23—H23120.2
C11—C10—H10120.1N3—C24—C23125.1 (6)
C9—C10—H10120.1N3—C24—H24117.4
C10—C11—C12119.1 (5)C23—C24—H24117.4
C10—C11—H11120.4N3—C25—C26125.4 (5)
C12—C11—H11120.4N3—C25—H25117.3
C13—C12—C11120.9 (5)C26—C25—H25117.3
C13—C12—H12119.6C25—C26—C22119.2 (5)
C11—C12—H12119.6C25—C26—H26120.4
C12—C13—C14120.1 (5)C22—C26—H26120.4
C12—C13—H13119.9
C8—N1—N2—C15162.2 (6)C12—C13—C14—C92.1 (9)
C6—C1—C2—C30.0C10—C9—C14—C132.5 (9)
C7—C1—C2—C3178.9 (4)C8—C9—C14—C13−177.5 (5)
C1—C2—C3—C40.0N1—N2—C15—C16177.4 (6)
C2—C3—C4—C50.0N2—C15—C16—C21−6.3 (11)
C3—C4—C5—C60.0N2—C15—C16—C17178.1 (7)
C4—C5—C6—C10.0C21—C16—C17—C18−0.7 (11)
C2—C1—C6—C50.0C15—C16—C17—C18175.0 (7)
C7—C1—C6—C5−178.9 (4)C16—C17—C18—C19−1.2 (11)
C2—C1—C7—O1−5.1 (6)C17—C18—C19—C202.8 (10)
C6—C1—C7—O1173.8 (4)C17—C18—C19—C22179.1 (6)
C2—C1—C7—C8173.7 (3)C18—C19—C20—C21−2.6 (9)
C6—C1—C7—C8−7.5 (6)C22—C19—C20—C21−178.9 (5)
N2—N1—C8—C9−178.8 (5)C19—C20—C21—C160.7 (10)
N2—N1—C8—C7−9.0 (8)C17—C16—C21—C200.9 (10)
O1—C7—C8—N1−84.7 (7)C15—C16—C21—C20−174.6 (6)
C1—C7—C8—N196.5 (6)C20—C19—C22—C23−29.9 (9)
O1—C7—C8—C985.3 (6)C18—C19—C22—C23153.9 (6)
C1—C7—C8—C9−93.5 (6)C20—C19—C22—C26148.4 (6)
N1—C8—C9—C100.1 (8)C18—C19—C22—C26−27.8 (9)
C7—C8—C9—C10−170.0 (5)C26—C22—C23—C24−2.2 (9)
N1—C8—C9—C14−179.9 (6)C19—C22—C23—C24176.3 (6)
C7—C8—C9—C1410.0 (8)C25—N3—C24—C23−2.9 (11)
C14—C9—C10—C11−4.3 (9)C22—C23—C24—N33.2 (11)
C8—C9—C10—C11175.7 (5)C24—N3—C25—C261.9 (10)
C9—C10—C11—C121.6 (9)N3—C25—C26—C22−1.2 (10)
C10—C11—C12—C133.0 (10)C23—C22—C26—C251.3 (9)
C11—C12—C13—C14−4.9 (10)C19—C22—C26—C25−177.2 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C26—H26···O1i0.952.573.502 (7)166

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2837).

References

  • Abbasi, A., Mohammadi Ziarani, G. & Tarighi, S. (2007). Acta Cryst. E63, o2579–o2580.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chowdhury, S., Drew, M. G. B. & Datta, D. (2003). Inorg. Chem. Commun.6, 1014–1016.
  • Liu, Q.-K., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2007). Acta Cryst. E63, o2646–o2647.
  • Schweizer, E. E., Hayes, J. E., Lee, K. J. & Rheingold, A. L. (1987). J. Org. Chem.52, 1324–1332.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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