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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o306.
Published online 2009 January 14. doi:  10.1107/S1600536809000993
PMCID: PMC2968300

N,N′-Bis(4-bromo­benzyl­idene)biphenyl-2,2′-diamine

Abstract

The complete molecule of the title Schiff base, C26H18Br2N2, is generated by crystallographic twofold symmetry. The aromatic rings of the biphenyl­ene portion of the mol­ecule are twisted, as shown by the dihedral of 61.8 (1)° formed between them.

Related literature

There are relatively few crystallographic reports of Schiff bases formed by condensing biphenyl-2,2′-diamine with aldehydes or ketones. See: Alajarín et al. (2007 [triangle]); Coxall et al. (2003 [triangle]); Cunningham et al. (2004 [triangle]); Finder et al. (1973 [triangle]); Pruszynski et al. (1992 [triangle]).

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Object name is e-65-0o306-scheme1.jpg

Experimental

Crystal data

  • C26H18Br2N2
  • M r = 518.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o306-efi1.jpg
  • a = 15.9691 (10) Å
  • b = 8.3482 (5) Å
  • c = 16.7767 (11) Å
  • V = 2236.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.64 mm−1
  • T = 295 (2) K
  • 0.28 × 0.25 × 0.19 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.429, T max = 0.545 (expected range = 0.394–0.501)
  • 10424 measured reflections
  • 2542 independent reflections
  • 1333 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.116
  • S = 0.98
  • 2542 reflections
  • 136 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.36 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1209 Friedel pairs
  • Flack parameter: −0.013 (15)

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); 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]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000993/tk2356sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000993/tk2356Isup2.hkl

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

Acknowledgments

We thank the Alzahra University Research Council and Natural Resources, and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Biphenyl-2,2'-diamine (5 mmol) and 4-bromobenzaldehyde (10 mmol) were dissolved in ethanol (50 ml). The solution was heated for 5 h; the solid that separated from the cooled solution was collected and recrystallized from chloroform; a second recrystallization was effected with ethanol. The yield as 90%. Analysis found: C 60.20, H 3.54, N 5.43; C26H18Br2N2 requires: C 60.26, H 3.50, N 5.41.

Refinement

Carbon-bound H atoms were placed in calculated positions [C—H 0.93 Å and Uiso(H) 1.2–1.5Ueq(C)] and were included in the refinement in the riding-model approximation.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001); displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. (Symmetry code: i = 2 - x, 3 - y, z).

Crystal data

C26H18Br2N2F(000) = 1032
Mr = 518.24Dx = 1.539 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 5898 reflections
a = 15.9691 (10) Åθ = 3.0–27.4°
b = 8.3482 (5) ŵ = 3.64 mm1
c = 16.7767 (11) ÅT = 295 K
V = 2236.6 (2) Å3Cuboid, light yellow
Z = 40.28 × 0.25 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer2542 independent reflections
Radiation source: fine-focus sealed tube1333 reflections with I > 2σ(I)
graphiteRint = 0.040
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = −18→20
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −10→10
Tmin = 0.429, Tmax = 0.545l = −21→21
10424 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.116w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
2542 reflectionsΔρmax = 0.28 e Å3
136 parametersΔρmin = −0.36 e Å3
1 restraintAbsolute structure: Flack (1983), 1209 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.013 (15)

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

xyzUiso*/Ueq
Br10.89090 (4)0.63217 (6)0.50003 (6)0.1058 (3)
N10.8979 (2)1.3119 (4)0.7320 (3)0.0604 (9)
C10.8877 (2)1.4642 (5)0.7689 (3)0.0555 (10)
C20.9576 (2)1.5394 (4)0.8036 (2)0.0537 (9)
C30.9461 (3)1.6846 (5)0.8415 (3)0.0650 (11)
H30.99201.73710.86360.078*
C40.8672 (3)1.7534 (6)0.8471 (4)0.0676 (13)
H40.86051.85140.87270.081*
C50.7989 (3)1.6768 (5)0.8150 (3)0.0685 (12)
H50.74591.72140.82050.082*
C60.8087 (2)1.5347 (5)0.7748 (3)0.0656 (12)
H60.76261.48540.75140.079*
C70.8654 (3)1.2832 (7)0.6649 (3)0.0633 (12)
H70.83811.36630.63870.076*
C80.8685 (3)1.1275 (5)0.6264 (3)0.0597 (11)
C90.8443 (3)1.1094 (5)0.5480 (3)0.0818 (14)
H90.82361.19730.52020.098*
C100.8505 (3)0.9629 (6)0.5101 (4)0.0891 (14)
H100.83460.95180.45700.107*
C110.8805 (3)0.8339 (6)0.5523 (3)0.0714 (13)
C120.9015 (3)0.8464 (5)0.6305 (3)0.0703 (13)
H120.91950.75660.65850.084*
C130.8961 (2)0.9926 (5)0.6683 (3)0.0646 (11)
H130.91081.00160.72170.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1445 (6)0.0704 (3)0.1026 (5)−0.0098 (2)0.0284 (5)−0.0131 (4)
N10.058 (2)0.0512 (18)0.072 (3)−0.0048 (15)0.0000 (19)−0.0029 (19)
C10.050 (3)0.058 (2)0.058 (3)0.0000 (18)0.0025 (18)0.009 (2)
C20.054 (2)0.052 (2)0.056 (2)−0.0007 (16)0.0007 (19)0.0069 (19)
C30.063 (3)0.064 (2)0.067 (3)−0.001 (2)−0.005 (2)−0.004 (2)
C40.081 (4)0.057 (3)0.065 (3)0.004 (2)−0.002 (3)−0.002 (2)
C50.059 (3)0.064 (2)0.082 (3)0.017 (2)0.008 (2)0.008 (2)
C60.052 (3)0.065 (3)0.080 (3)−0.0025 (19)0.000 (2)0.014 (2)
C70.066 (3)0.066 (3)0.058 (3)0.000 (2)−0.007 (2)0.010 (2)
C80.062 (2)0.065 (3)0.052 (3)−0.0084 (18)−0.002 (2)0.001 (2)
C90.111 (4)0.068 (3)0.066 (3)0.004 (3)−0.020 (3)0.002 (2)
C100.127 (4)0.075 (3)0.066 (3)−0.001 (3)−0.024 (4)0.010 (3)
C110.065 (3)0.084 (3)0.065 (3)−0.006 (2)0.008 (2)0.004 (3)
C120.070 (3)0.058 (2)0.083 (4)−0.0047 (19)−0.004 (3)0.015 (2)
C130.074 (3)0.060 (3)0.059 (3)0.001 (2)−0.008 (2)0.006 (2)

Geometric parameters (Å, °)

Br1—C111.906 (5)C6—H60.9300
N1—C71.262 (6)C7—C81.452 (7)
N1—C11.424 (6)C7—H70.9300
C1—C61.395 (5)C8—C91.378 (7)
C1—C21.407 (6)C8—C131.399 (6)
C2—C31.381 (6)C9—C101.383 (6)
C2—C2i1.506 (7)C9—H90.9300
C3—C41.389 (6)C10—C111.376 (7)
C3—H30.9300C10—H100.9300
C4—C51.373 (7)C11—C121.358 (8)
C4—H40.9300C12—C131.378 (6)
C5—C61.374 (6)C12—H120.9300
C5—H50.9300C13—H130.9300
C7—N1—C1120.7 (4)N1—C7—H7118.2
C6—C1—C2120.0 (4)C8—C7—H7118.2
C6—C1—N1120.8 (4)C9—C8—C13118.6 (4)
C2—C1—N1119.2 (3)C9—C8—C7120.9 (4)
C3—C2—C1118.5 (4)C13—C8—C7120.5 (5)
C3—C2—C2i120.2 (4)C8—C9—C10121.1 (4)
C1—C2—C2i121.2 (4)C8—C9—H9119.5
C2—C3—C4121.0 (4)C10—C9—H9119.5
C2—C3—H3119.5C9—C10—C11118.7 (5)
C4—C3—H3119.5C9—C10—H10120.7
C5—C4—C3120.1 (4)C11—C10—H10120.7
C5—C4—H4120.0C12—C11—C10121.6 (5)
C3—C4—H4120.0C12—C11—Br1119.4 (4)
C6—C5—C4120.3 (4)C10—C11—Br1119.0 (4)
C6—C5—H5119.8C11—C12—C13119.8 (5)
C4—C5—H5119.8C11—C12—H12120.1
C5—C6—C1120.1 (4)C13—C12—H12120.1
C5—C6—H6119.9C12—C13—C8120.1 (5)
C1—C6—H6119.9C12—C13—H13119.9
N1—C7—C8123.6 (5)C8—C13—H13119.9
C7—N1—C1—C648.5 (6)C1—N1—C7—C8−175.6 (4)
C7—N1—C1—C2−135.0 (5)N1—C7—C8—C9−169.2 (5)
C6—C1—C2—C3−1.4 (6)N1—C7—C8—C1310.8 (7)
N1—C1—C2—C3−177.9 (4)C13—C8—C9—C10−2.8 (8)
C6—C1—C2—C2i175.4 (3)C7—C8—C9—C10177.2 (5)
N1—C1—C2—C2i−1.1 (5)C8—C9—C10—C110.6 (8)
C1—C2—C3—C41.6 (6)C9—C10—C11—C122.1 (7)
C2i—C2—C3—C4−175.3 (4)C9—C10—C11—Br1−179.0 (4)
C2—C3—C4—C50.2 (8)C10—C11—C12—C13−2.7 (7)
C3—C4—C5—C6−2.2 (8)Br1—C11—C12—C13178.5 (3)
C4—C5—C6—C12.4 (7)C11—C12—C13—C80.4 (7)
C2—C1—C6—C5−0.6 (7)C9—C8—C13—C122.2 (7)
N1—C1—C6—C5175.9 (4)C7—C8—C13—C12−177.8 (4)

Symmetry codes: (i) −x+2, −y+3, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2356).

References

  • Alajarín, M., Bonillo, B., Sánchez-Andrada, P., Vidal, Á. & Bautista, D. (2007). J. Org. Chem.72, 5863–5866. [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Coxall, R. A., Lindoy, L. F., Miller, H. A., Parkin, A., Parsons, S., Tasker, P. A. & White, D. J. (2003). Dalton Trans. pp. 55–64.
  • Cunningham, D., Gilligan, K., Hannon, M., Kelly, K., McArdle, P. & O’Malley, A. (2004). Organometallics, 23, 984–994.
  • Finder, C. J., Newton, M. G. & Allinger, N. L. (1973). J. Chem. Soc. Perkin Trans. 2, pp. 1929–1932.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Pruszynski, P., Leffek, K. T., Borecka, B. & Cameron, T. S. (1992). Acta Cryst. C48, 1638–1641.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • 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