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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2316.
Published online 2010 August 18. doi:  10.1107/S1600536810032034
PMCID: PMC3007987

Ortho­rhom­bic modification of bis­[4-(3-pyridyl­methyl­idene­amino)­phen­yl]methane

Abstract

The title compound, C25H20N4, is a disubstituted methane derivative having two pyridyl­methyl­ene­amino­phenyl arms, one of which is essentially rigid as all atoms lie on a plane (r.m.s. deviation = 0.074 Å), whereas the other is twisted [dihedral angle between the phenyl­ene and pyridyl rings = 51.1 (4)°]. The angle at the methyl­ene C atom is 113.2 (2)°.

Related literature

For the monoclinic modification, see: Wang et al. (2005 [triangle]).

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Object name is e-66-o2316-scheme1.jpg

Experimental

Crystal data

  • C25H20N4
  • M r = 376.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2316-efi1.jpg
  • a = 11.4213 (4) Å
  • b = 4.6181 (2) Å
  • c = 37.3048 (15) Å
  • V = 1967.63 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • 9233 measured reflections
  • 1761 independent reflections
  • 1450 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.109
  • S = 0.92
  • 1761 reflections
  • 262 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.11 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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032034/nk2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032034/nk2051Isup2.hkl

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

Acknowledgments

We thank the Higher Education Commission of Pakistan, GC University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have synthesized bis[4-(3-pyridylmethyleneamino)phenyl]methane (Scheme I) for use in cocrystallization studies. The compound has previously been reported to belong to the non-centric Pc space group [a = 18.751 (5), b = 4.641 (2), c = 11.387 (1) Å, β = 98.39 (2) °] (Wang et al., 2005). The atoms of one of the two pyridylmethyleneaminophenylarms of the approximately V-shaped molecule all lie on a plane; for the other arm, the two aromatic rings are aligned at 53.9 (2) °]. The present orthorhombic modification (Fig. 1) has one axis that is doubled [c = 37.3048 (15), b = 4.6181 (2), a = 11.4213 (4) Å]. The principal features are similar to those of the reported structure.

Experimental

The compound was synthesized from the condensation of 4,4'-diaminodiphenylmethane and 3-pyridinecarboxaldehyde in ethanol (Wang et al., 2005), and crystals were obtained upon recrystallization from ethyl acetate.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). Friedel pairs (1535) were merged.

Figures

Fig. 1.
Displacement ellipsoid plot of C25H20N4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C25H20N4F(000) = 792
Mr = 376.45Dx = 1.271 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1793 reflections
a = 11.4213 (4) Åθ = 3.3–20.6°
b = 4.6181 (2) ŵ = 0.08 mm1
c = 37.3048 (15) ÅT = 293 K
V = 1967.63 (14) Å3Prism, yellow
Z = 40.35 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer1450 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 25.0°, θmin = 3.3°
[var phi] and ω scansh = −13→12
9233 measured reflectionsk = −5→5
1761 independent reflectionsl = −43→44

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.081P)2] where P = (Fo2 + 2Fc2)/3
1761 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.11 e Å3
1 restraintΔρmin = −0.11 e Å3

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

xyzUiso*/Ueq
N1−0.0359 (3)1.7957 (7)0.50015 (10)0.0616 (8)
N20.1337 (2)1.1963 (5)0.43344 (7)0.0397 (6)
N30.4326 (3)0.9705 (6)0.20004 (8)0.0532 (7)
N40.7055 (3)1.3287 (10)0.11332 (10)0.0816 (11)
C10.1358 (3)1.5338 (6)0.48188 (8)0.0375 (7)
C20.1996 (3)1.6715 (8)0.50825 (9)0.0522 (9)
H20.27891.63160.51100.063*
C30.1457 (4)1.8681 (8)0.53055 (9)0.0576 (10)
H30.18741.96150.54860.069*
C40.0294 (4)1.9221 (8)0.52547 (10)0.0577 (10)
H4−0.00672.05510.54060.069*
C50.0193 (3)1.6096 (8)0.47908 (10)0.0529 (9)
H5−0.02401.52290.46090.063*
C60.1904 (3)1.3248 (7)0.45776 (9)0.0429 (8)
H60.26981.28490.46040.052*
C70.1904 (3)0.9962 (6)0.41026 (8)0.0357 (7)
C80.3029 (3)0.8895 (6)0.41450 (8)0.0409 (7)
H80.34790.94970.43390.049*
C90.3488 (3)0.6942 (6)0.39020 (9)0.0415 (8)
H90.42410.62310.39370.050*
C100.2848 (3)0.6020 (6)0.36067 (8)0.0370 (7)
C110.1720 (3)0.7078 (7)0.35684 (9)0.0440 (8)
H110.12700.64910.33740.053*
C120.1252 (3)0.8988 (7)0.38142 (9)0.0416 (7)
H120.04860.96300.37860.050*
C130.3353 (3)0.3988 (7)0.33309 (9)0.0459 (8)
H13A0.27980.24390.32870.055*
H13B0.40620.31250.34260.055*
C140.3636 (3)0.5460 (6)0.29792 (9)0.0419 (7)
C150.4547 (3)0.7423 (7)0.29520 (9)0.0452 (8)
H150.49980.78260.31530.054*
C160.4800 (3)0.8798 (7)0.26323 (9)0.0469 (8)
H160.54221.00920.26210.056*
C170.4139 (3)0.8275 (7)0.23287 (9)0.0480 (8)
C180.3207 (3)0.6355 (9)0.23547 (10)0.0614 (10)
H180.27380.60040.21560.074*
C190.2972 (3)0.4961 (8)0.26751 (10)0.0572 (9)
H190.23530.36560.26860.069*
C200.5355 (4)1.0079 (8)0.18865 (9)0.0565 (10)
H200.59730.92750.20150.068*
C210.5619 (3)1.1718 (8)0.15619 (9)0.0517 (9)
C220.6740 (3)1.1852 (9)0.14284 (10)0.0683 (11)
H220.73221.08700.15530.082*
C230.6200 (4)1.4715 (11)0.09659 (12)0.0764 (13)
H230.63911.57370.07590.092*
C240.5058 (4)1.4774 (9)0.10794 (11)0.0704 (11)
H240.44961.58250.09540.084*
C250.4766 (3)1.3259 (9)0.13793 (11)0.0607 (10)
H250.39971.32570.14610.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0476 (17)0.0680 (19)0.069 (2)0.0030 (15)0.0021 (16)−0.0211 (17)
N20.0379 (14)0.0420 (14)0.0392 (15)0.0028 (11)0.0002 (13)−0.0020 (12)
N30.0526 (19)0.0636 (18)0.0434 (16)0.0009 (15)0.0023 (14)0.0059 (14)
N40.059 (2)0.125 (3)0.061 (2)−0.008 (2)0.0122 (18)0.011 (2)
C10.0387 (17)0.0362 (15)0.0375 (16)−0.0039 (13)0.0007 (14)0.0037 (13)
C20.048 (2)0.060 (2)0.049 (2)0.0018 (16)−0.0086 (16)−0.0053 (17)
C30.068 (3)0.061 (2)0.044 (2)−0.0018 (19)−0.0119 (19)−0.0096 (17)
C40.066 (3)0.054 (2)0.053 (2)0.0022 (19)0.012 (2)−0.0063 (17)
C50.041 (2)0.059 (2)0.058 (2)−0.0039 (17)−0.0033 (17)−0.0148 (18)
C60.0354 (17)0.0451 (16)0.0483 (19)0.0002 (14)−0.0001 (15)0.0008 (15)
C70.0358 (16)0.0334 (13)0.0379 (16)−0.0009 (13)0.0035 (13)0.0041 (13)
C80.0374 (17)0.0462 (16)0.0390 (17)−0.0015 (14)−0.0040 (14)0.0016 (15)
C90.0315 (16)0.0404 (16)0.053 (2)0.0017 (13)0.0014 (15)0.0081 (15)
C100.0391 (17)0.0310 (14)0.0410 (18)−0.0004 (12)0.0051 (14)0.0085 (13)
C110.0397 (17)0.0465 (17)0.0457 (19)−0.0002 (14)−0.0029 (15)−0.0093 (15)
C120.0320 (16)0.0445 (16)0.0481 (19)0.0041 (13)−0.0017 (15)−0.0021 (15)
C130.0472 (19)0.0360 (15)0.055 (2)0.0048 (14)0.0089 (16)0.0036 (15)
C140.0427 (18)0.0372 (15)0.0459 (19)0.0064 (14)0.0083 (16)−0.0029 (15)
C150.0485 (19)0.0443 (16)0.0427 (18)0.0014 (14)−0.0003 (15)−0.0013 (15)
C160.046 (2)0.0480 (17)0.0469 (19)−0.0036 (15)0.0033 (17)−0.0009 (15)
C170.046 (2)0.052 (2)0.0457 (19)0.0036 (16)0.0028 (17)0.0021 (15)
C180.057 (2)0.081 (3)0.046 (2)−0.008 (2)−0.0074 (18)0.002 (2)
C190.050 (2)0.059 (2)0.062 (2)−0.0119 (17)0.0007 (17)0.0002 (18)
C200.058 (2)0.065 (2)0.047 (2)0.0088 (19)0.0000 (17)0.0021 (18)
C210.051 (2)0.062 (2)0.042 (2)0.0009 (17)−0.0007 (17)−0.0020 (17)
C220.054 (2)0.100 (3)0.050 (2)0.003 (2)0.0016 (19)0.005 (2)
C230.086 (3)0.096 (3)0.047 (2)−0.015 (3)0.009 (2)0.010 (2)
C240.074 (3)0.082 (3)0.055 (2)0.003 (2)0.002 (2)0.016 (2)
C250.053 (2)0.080 (2)0.048 (2)−0.0018 (19)0.0048 (19)0.0078 (18)

Geometric parameters (Å, °)

N1—C51.325 (5)C11—C121.380 (4)
N1—C41.338 (5)C11—H110.9300
N2—C61.263 (4)C12—H120.9300
N2—C71.422 (4)C13—C141.513 (4)
N3—C201.262 (5)C13—H13A0.9700
N3—C171.408 (4)C13—H13B0.9700
N4—C231.334 (6)C14—C151.384 (4)
N4—C221.335 (5)C14—C191.384 (5)
C1—C51.380 (5)C15—C161.382 (5)
C1—C21.379 (5)C15—H150.9300
C1—C61.459 (4)C16—C171.382 (5)
C2—C31.377 (5)C16—H160.9300
C2—H20.9300C17—C181.388 (5)
C3—C41.364 (5)C18—C191.384 (5)
C3—H30.9300C18—H180.9300
C4—H40.9300C19—H190.9300
C5—H50.9300C20—C211.459 (5)
C6—H60.9300C20—H200.9300
C7—C81.385 (4)C21—C221.375 (5)
C7—C121.384 (4)C21—C251.386 (5)
C8—C91.382 (4)C22—H220.9300
C8—H80.9300C23—C241.372 (6)
C9—C101.389 (4)C23—H230.9300
C9—H90.9300C24—C251.361 (5)
C10—C111.386 (4)C24—H240.9300
C10—C131.507 (4)C25—H250.9300
C5—N1—C4115.9 (3)C10—C13—H13A108.9
C6—N2—C7120.6 (3)C14—C13—H13A108.9
C20—N3—C17119.9 (3)C10—C13—H13B108.9
C23—N4—C22115.7 (4)C14—C13—H13B108.9
C5—C1—C2116.5 (3)H13A—C13—H13B107.8
C5—C1—C6122.2 (3)C15—C14—C19117.4 (3)
C2—C1—C6121.3 (3)C15—C14—C13121.2 (3)
C3—C2—C1120.0 (3)C19—C14—C13121.3 (3)
C3—C2—H2120.0C16—C15—C14121.4 (3)
C1—C2—H2120.0C16—C15—H15119.3
C4—C3—C2118.1 (3)C14—C15—H15119.3
C4—C3—H3120.9C15—C16—C17120.9 (3)
C2—C3—H3120.9C15—C16—H16119.6
N1—C4—C3124.2 (3)C17—C16—H16119.6
N1—C4—H4117.9C16—C17—C18118.2 (3)
C3—C4—H4117.9C16—C17—N3123.2 (3)
N1—C5—C1125.4 (3)C18—C17—N3118.5 (3)
N1—C5—H5117.3C19—C18—C17120.4 (3)
C1—C5—H5117.3C19—C18—H18119.8
N2—C6—C1122.3 (3)C17—C18—H18119.8
N2—C6—H6118.8C18—C19—C14121.6 (3)
C1—C6—H6118.8C18—C19—H19119.2
C8—C7—C12118.2 (3)C14—C19—H19119.2
C8—C7—N2125.7 (3)N3—C20—C21122.9 (3)
C12—C7—N2116.1 (3)N3—C20—H20118.6
C9—C8—C7120.6 (3)C21—C20—H20118.6
C9—C8—H8119.7C22—C21—C25117.0 (3)
C7—C8—H8119.7C22—C21—C20121.1 (4)
C8—C9—C10121.4 (3)C25—C21—C20121.9 (3)
C8—C9—H9119.3N4—C22—C21124.9 (4)
C10—C9—H9119.3N4—C22—H22117.5
C11—C10—C9117.6 (3)C21—C22—H22117.5
C11—C10—C13120.3 (3)N4—C23—C24124.2 (4)
C9—C10—C13122.1 (3)N4—C23—H23117.9
C12—C11—C10121.1 (3)C24—C23—H23117.9
C12—C11—H11119.4C25—C24—C23118.4 (4)
C10—C11—H11119.4C25—C24—H24120.8
C11—C12—C7121.1 (3)C23—C24—H24120.8
C11—C12—H12119.5C24—C25—C21119.7 (4)
C7—C12—H12119.5C24—C25—H25120.1
C10—C13—C14113.2 (2)C21—C25—H25120.1
C5—C1—C2—C31.4 (5)C10—C13—C14—C1569.5 (4)
C6—C1—C2—C3179.9 (3)C10—C13—C14—C19−108.5 (3)
C1—C2—C3—C4−0.5 (5)C19—C14—C15—C16−1.1 (5)
C5—N1—C4—C3−0.5 (6)C13—C14—C15—C16−179.2 (3)
C2—C3—C4—N10.1 (6)C14—C15—C16—C170.7 (5)
C4—N1—C5—C11.6 (6)C15—C16—C17—C180.6 (5)
C2—C1—C5—N1−2.0 (5)C15—C16—C17—N3177.2 (3)
C6—C1—C5—N1179.5 (3)C20—N3—C17—C1643.1 (5)
C7—N2—C6—C1179.4 (3)C20—N3—C17—C18−140.4 (4)
C5—C1—C6—N2−1.6 (5)C16—C17—C18—C19−1.5 (5)
C2—C1—C6—N2180.0 (3)N3—C17—C18—C19−178.3 (3)
C6—N2—C7—C810.1 (4)C17—C18—C19—C141.1 (6)
C6—N2—C7—C12−171.1 (3)C15—C14—C19—C180.2 (5)
C12—C7—C8—C90.9 (4)C13—C14—C19—C18178.3 (3)
N2—C7—C8—C9179.8 (3)C17—N3—C20—C21−175.5 (3)
C7—C8—C9—C100.8 (4)N3—C20—C21—C22−173.9 (4)
C8—C9—C10—C11−1.4 (4)N3—C20—C21—C257.6 (6)
C8—C9—C10—C13177.4 (3)C23—N4—C22—C211.3 (7)
C9—C10—C11—C120.3 (4)C25—C21—C22—N4−1.8 (6)
C13—C10—C11—C12−178.6 (3)C20—C21—C22—N4179.7 (4)
C10—C11—C12—C71.5 (5)C22—N4—C23—C240.0 (7)
C8—C7—C12—C11−2.1 (4)N4—C23—C24—C25−0.8 (7)
N2—C7—C12—C11178.9 (3)C23—C24—C25—C210.2 (6)
C11—C10—C13—C1471.8 (4)C22—C21—C25—C240.9 (5)
C9—C10—C13—C14−107.1 (3)C20—C21—C25—C24179.4 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2051).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Q., Pi, X.-D. & Su, C.-Y. (2005). Acta Cryst. C61, o73–o74. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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