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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1887.
Published online 2010 July 3. doi:  10.1107/S160053681002533X
PMCID: PMC3007545

(E)-1-(4-Meth­oxy­benzyl­idene)-2-phenyl­hydrazine

Abstract

In the title compound, C14H14N2O, the dihedral angle between the aromatic rings is 9.30 (6)°. In the crystal, mol­ecules are linked by C—H(...)π and N—H(...)π inter­actions.

Related literature

For related structures, see: Tunç et al. (2003 [triangle]); Harada et al. (2004 [triangle]).

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Object name is e-66-o1887-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O
  • M r = 226.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1887-efi1.jpg
  • a = 5.8021 (2) Å
  • b = 7.5819 (2) Å
  • c = 27.7907 (9) Å
  • β = 95.808 (1)°
  • V = 1216.26 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.30 × 0.16 × 0.14 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.942, T max = 0.959
  • 18675 measured reflections
  • 3004 independent reflections
  • 2257 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.124
  • S = 1.01
  • 3004 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002533X/hb5529sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002533X/hb5529Isup2.hkl

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The crystal structure of (II) i.e., N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine (Tunç et al. 2003) and N-(4-methoxybenzylidene)aniline (Harada et al. 2004) have been published which are related to the title compound (I, Fig. 1).

In (I) the phenyl ring A (C1–C6) of phenylhydrazide and B (C8–C13) of 4-anisaldehyde are planar with r. m. s. deviation of 0.0015 and 0.0096 Å, respectively. The dihedral angle between A/B is 9.30 (6)°. The central group C (N1/N2/C7) is of course planar and the orientation of A/C and B/C is 11.59 (17) and 2.89 (18)°, respectively. The molecules are essentially monomer. Due to the packing and unavailabilty of strong acceptor atom, the H-atom of N—H is not directly involved in H-bonding. The molecules are stabilized through C—H···π and N—H···π interactions (Table 1).

Experimental

Equimolar quantities of phenylhydrazine and 4-methoxybenzaldehyde were refluxed in methanol for 45 min resulting in yellow solution. The solution was kept at room temperature which affoarded yellow needles of (I) after 72 h.

Refinement

Although all H-atoms appear in the difference Fourier map but were positioned geometrically (N–H = 0.86, C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by circles of arbitrary radius.

Crystal data

C14H14N2OF(000) = 480
Mr = 226.27Dx = 1.236 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2257 reflections
a = 5.8021 (2) Åθ = 2.8–28.4°
b = 7.5819 (2) ŵ = 0.08 mm1
c = 27.7907 (9) ÅT = 296 K
β = 95.808 (1)°Cut needle, yellow
V = 1216.26 (7) Å30.30 × 0.16 × 0.14 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer3004 independent reflections
Radiation source: fine-focus sealed tube2257 reflections with I > 2σ(I)
graphiteRint = 0.028
Detector resolution: 8.20 pixels mm-1θmax = 28.4°, θmin = 2.8°
ω scansh = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −9→10
Tmin = 0.942, Tmax = 0.959l = −37→37
18675 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2017P] where P = (Fo2 + 2Fc2)/3
3004 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.

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

xyzUiso*/Ueq
O10.58571 (17)0.12817 (13)0.05523 (3)0.0593 (3)
N11.0199 (2)0.27807 (16)0.32418 (4)0.0576 (4)
N20.99619 (18)0.22429 (14)0.27710 (4)0.0475 (3)
C11.1991 (2)0.21880 (15)0.35653 (4)0.0431 (4)
C21.3896 (2)0.13069 (16)0.34188 (5)0.0486 (4)
C31.5625 (2)0.07433 (18)0.37608 (6)0.0594 (5)
C41.5495 (3)0.1038 (2)0.42465 (6)0.0659 (5)
C51.3613 (3)0.1917 (2)0.43908 (5)0.0616 (5)
C61.1872 (2)0.24896 (17)0.40553 (5)0.0520 (4)
C70.8064 (2)0.26802 (16)0.25267 (4)0.0458 (4)
C80.7500 (2)0.22464 (14)0.20197 (4)0.0404 (3)
C90.9001 (2)0.13387 (15)0.17420 (4)0.0436 (4)
C100.8384 (2)0.10202 (16)0.12601 (4)0.0458 (4)
C110.6270 (2)0.16101 (15)0.10379 (4)0.0438 (4)
C120.4738 (2)0.24744 (16)0.13072 (4)0.0458 (4)
C130.5363 (2)0.27705 (16)0.17934 (4)0.0449 (4)
C140.3755 (3)0.1915 (3)0.03100 (5)0.0771 (6)
H10.920650.350710.333930.0691*
H21.400530.109820.309220.0583*
H31.690100.015380.366200.0713*
H41.666850.064570.447400.0791*
H51.351700.212590.471790.0739*
H61.060520.308340.415700.0624*
H70.698290.331190.268240.0550*
H91.042770.094900.188550.0523*
H100.938760.040440.108070.0550*
H120.330600.285090.116280.0550*
H130.432350.333790.197490.0539*
H14A0.247130.138410.044810.1156*
H14B0.368470.16173−0.002690.1156*
H14C0.368280.317310.034460.1156*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0679 (6)0.0706 (6)0.0389 (5)0.0039 (5)0.0023 (4)−0.0054 (4)
N10.0616 (7)0.0695 (7)0.0400 (6)0.0237 (6)−0.0038 (5)−0.0104 (5)
N20.0537 (6)0.0484 (6)0.0398 (6)0.0048 (4)0.0018 (5)−0.0027 (4)
C10.0458 (6)0.0395 (6)0.0431 (7)0.0005 (5)0.0004 (5)−0.0025 (5)
C20.0480 (7)0.0464 (6)0.0512 (7)−0.0004 (5)0.0045 (5)−0.0080 (5)
C30.0476 (7)0.0518 (7)0.0771 (10)0.0065 (6)−0.0020 (7)−0.0102 (7)
C40.0627 (9)0.0603 (8)0.0690 (10)0.0073 (7)−0.0207 (7)−0.0022 (7)
C50.0714 (9)0.0650 (9)0.0458 (8)0.0017 (7)−0.0066 (7)−0.0033 (6)
C60.0560 (7)0.0546 (8)0.0452 (7)0.0065 (6)0.0035 (6)−0.0055 (5)
C70.0503 (7)0.0449 (6)0.0421 (7)0.0051 (5)0.0038 (5)−0.0012 (5)
C80.0444 (6)0.0370 (5)0.0400 (6)−0.0027 (4)0.0048 (5)0.0016 (4)
C90.0412 (6)0.0434 (6)0.0462 (7)0.0004 (5)0.0044 (5)0.0036 (5)
C100.0465 (6)0.0467 (6)0.0458 (7)0.0008 (5)0.0125 (5)−0.0029 (5)
C110.0509 (7)0.0430 (6)0.0376 (6)−0.0061 (5)0.0050 (5)−0.0006 (5)
C120.0413 (6)0.0495 (7)0.0457 (7)−0.0009 (5)−0.0004 (5)−0.0010 (5)
C130.0435 (6)0.0460 (6)0.0456 (7)0.0027 (5)0.0070 (5)−0.0024 (5)
C140.0929 (12)0.0906 (12)0.0443 (8)0.0169 (10)−0.0095 (8)−0.0024 (8)

Geometric parameters (Å, °)

O1—C111.3694 (14)C10—C111.3902 (16)
O1—C141.416 (2)C11—C121.3836 (16)
N1—N21.3641 (16)C12—C131.3815 (16)
N1—C11.3792 (16)C2—H20.9300
N2—C71.2776 (16)C3—H30.9300
N1—H10.8600C4—H40.9300
C1—C61.3894 (18)C5—H50.9300
C1—C21.3874 (17)C6—H60.9300
C2—C31.3782 (19)C7—H70.9300
C3—C41.378 (2)C9—H90.9300
C4—C51.373 (2)C10—H100.9300
C5—C61.374 (2)C12—H120.9300
C7—C81.4516 (16)C13—H130.9300
C8—C131.3903 (16)C14—H14A0.9600
C8—C91.4013 (16)C14—H14B0.9600
C9—C101.3722 (16)C14—H14C0.9600
C11—O1—C14117.60 (10)C3—C2—H2120.00
N2—N1—C1121.61 (11)C2—C3—H3119.00
N1—N2—C7115.47 (11)C4—C3—H3119.00
N2—N1—H1119.00C3—C4—H4120.00
C1—N1—H1119.00C5—C4—H4120.00
N1—C1—C2122.42 (11)C4—C5—H5120.00
N1—C1—C6118.45 (11)C6—C5—H5120.00
C2—C1—C6119.14 (11)C1—C6—H6120.00
C1—C2—C3119.53 (12)C5—C6—H6120.00
C2—C3—C4121.14 (13)N2—C7—H7118.00
C3—C4—C5119.26 (14)C8—C7—H7118.00
C4—C5—C6120.46 (13)C8—C9—H9120.00
C1—C6—C5120.47 (12)C10—C9—H9120.00
N2—C7—C8123.68 (11)C9—C10—H10120.00
C9—C8—C13117.82 (10)C11—C10—H10120.00
C7—C8—C9123.66 (10)C11—C12—H12120.00
C7—C8—C13118.52 (10)C13—C12—H12120.00
C8—C9—C10120.57 (11)C8—C13—H13119.00
C9—C10—C11120.55 (11)C12—C13—H13119.00
O1—C11—C12124.15 (11)O1—C14—H14A109.00
O1—C11—C10115.96 (10)O1—C14—H14B109.00
C10—C11—C12119.89 (10)O1—C14—H14C109.00
C11—C12—C13119.12 (11)H14A—C14—H14B109.00
C8—C13—C12121.99 (11)H14A—C14—H14C109.00
C1—C2—H2120.00H14B—C14—H14C109.00
C14—O1—C11—C121.90 (19)C4—C5—C6—C10.0 (2)
C14—O1—C11—C10−177.93 (13)N2—C7—C8—C13179.04 (12)
N2—N1—C1—C213.07 (18)N2—C7—C8—C9−1.57 (19)
N2—N1—C1—C6−166.94 (11)C7—C8—C13—C12177.18 (11)
C1—N1—N2—C7170.35 (11)C9—C8—C13—C12−2.24 (17)
N1—N2—C7—C8179.36 (11)C7—C8—C9—C10−177.96 (11)
N1—C1—C6—C5179.76 (12)C13—C8—C9—C101.44 (17)
N1—C1—C2—C3−179.78 (12)C8—C9—C10—C110.73 (18)
C6—C1—C2—C30.24 (18)C9—C10—C11—C12−2.17 (18)
C2—C1—C6—C5−0.26 (19)C9—C10—C11—O1177.67 (11)
C1—C2—C3—C40.1 (2)O1—C11—C12—C13−178.45 (11)
C2—C3—C4—C5−0.3 (2)C10—C11—C12—C131.38 (18)
C3—C4—C5—C60.3 (2)C11—C12—C13—C80.85 (18)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 phenyl ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···Cg1i0.862.693.3484 (13)146
C3—H3···Cg1ii0.932.633.3796 (14)138

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5529).

References

  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Harada, J., Harakawa, M. & Ogawa, K. (2004). Acta Cryst. B60, 578–588. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tunç, T., Sarı, M., Yagbasan, R., Tezcan, H. & Şahin, E. (2003). Acta Cryst. C59, o192–o193. [PubMed]

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