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Acta Cryst. (2009). E65, o306    [ doi:10.1107/S1600536809000993 ]

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

S. Dehghanpour, S. Asadizadeh, S. Gao and S. W. Ng

Abstract top

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 top

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); Coxall et al. (2003); Cunningham et al. (2004); Finder et al. (1973); Pruszynski et al. (1992).

Experimental top

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 top

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.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] 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).
N,N'-Bis(4-bromobenzylidene)biphenyl-2,2'-diamine top
Crystal data top
C26H18Br2N2F(000) = 1032
Mr = 518.24Dx = 1.539 Mg m−3
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 mm−1
c = 16.7767 (11) ÅT = 295 K
V = 2236.6 (2) Å3Cuboid, light yellow
Z = 40.28 × 0.25 × 0.19 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2542 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 top
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) = 0.116 w = 1/[σ2(Fo2) + (0.0547P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
2542 reflectionsΔρmax = 0.28 e Å−3
136 parametersΔρmin = −0.36 e Å−3
1 restraintAbsolute structure: Flack (1983), 1209 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.013 (15)
Crystal data top
C26H18Br2N2V = 2236.6 (2) Å3
Mr = 518.24Z = 4
Orthorhombic, Aba2Mo Kα radiation
a = 15.9691 (10) ŵ = 3.64 mm−1
b = 8.3482 (5) ÅT = 295 K
c = 16.7767 (11) Å0.28 × 0.25 × 0.19 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2542 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1333 reflections with I > 2σ(I)
Tmin = 0.429, Tmax = 0.545Rint = 0.040
10424 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.116Δρmax = 0.28 e Å−3
S = 0.98Δρmin = −0.36 e Å−3
2542 reflectionsAbsolute structure: Flack (1983), 1209 Friedel pairs
136 parametersFlack parameter: −0.013 (15)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Acknowledgements top

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

references
References top

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