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Acta Cryst. (2009). E65, o307    [ doi:10.1107/S1600536809000804 ]

N,N'-Bis(3-phenylallylidene)biphenyl-2,2'-diamine

S. Dehghanpour, F. Afshariazar, S. Gao and S. W. Ng

Abstract top

In the title Schiff base, C30H24N2, the complete molecule is generated by a crystallographic twofold axis; the aromatic rings of the biphenyl unit are twisted by 60.78 (1)°. The imine double bond has a trans configuration.

Related literature top

For a list of the crystal structures of Schiff bases formed by condensing biphenyl-2,2'-diamine with aldehydes or ketones, see: Dehghanpour et al. (2009).

Experimental top

Biphenyl-2,2'-diamine (5 mmol) and cinnamaldehyde (10 mmol) were dissolved in diethyl ether (50 ml). The mixture was stirred for 30 min. Evaporation of the solvent gave a solid that was recrystallized from ethanol twice. Yield: 80%. CH&N elemental analysis. Calculated for C30H24N2: C 87.35, H 5.86, N 6.79%; found: C 87.30, H 5.81, N 9.82%.

Refinement top

H atoms were placed in calculated positions [C—H 0.93 Å and Uiso(H) 1.2Ueq(C)], and were included in the refinement in the riding-model approximation. Friedel pairs were merged

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. Anisotropic displacement ellipsoid plot (Barbour, 2001); displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. (Symmetry code i: -x, -y, z).
N,N'-Bis(3-phenylallylidene)biphenyl-2,2'-diamine top
Crystal data top
C30H24N2F(000) = 1744
Mr = 412.51Dx = 1.161 Mg m−3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 7049 reflections
a = 15.4354 (12) Åθ = 3.2–27.5°
b = 31.783 (2) ŵ = 0.07 mm−1
c = 9.6188 (8) ÅT = 295 K
V = 4718.8 (6) Å3Cuboid, light yellow
Z = 80.27 × 0.21 × 0.16 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1427 independent reflections
Radiation source: fine-focus sealed tube1021 reflections with I > 2σ(I)
graphiteRint = 0.029
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −20→19
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −41→41
Tmin = 0.982, Tmax = 0.989l = −12→12
11331 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0608P)2 + 0.8672P]
where P = (Fo2 + 2Fc2)/3
1427 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.11 e Å−3
1 restraintΔρmin = −0.15 e Å−3
Crystal data top
C30H24N2V = 4718.8 (6) Å3
Mr = 412.51Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 15.4354 (12) ŵ = 0.07 mm−1
b = 31.783 (2) ÅT = 295 K
c = 9.6188 (8) Å0.27 × 0.21 × 0.16 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1427 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1021 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.989Rint = 0.029
11331 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.11 e Å−3
S = 1.07Δρmin = −0.15 e Å−3
1427 reflectionsAbsolute structure: ?
145 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
C1−0.01193 (13)0.05064 (6)0.5676 (2)0.0523 (5)
C2−0.02328 (13)0.02045 (6)0.4634 (2)0.0541 (5)
C3−0.07746 (15)0.02974 (7)0.3523 (3)0.0641 (6)
H3A−0.08590.00970.28310.077*
C4−0.11943 (16)0.06833 (8)0.3424 (3)0.0724 (7)
H4A−0.15610.07390.26790.087*
C5−0.10622 (16)0.09796 (7)0.4433 (3)0.0695 (7)
H5A−0.13330.12400.43630.083*
C6−0.05334 (14)0.08962 (6)0.5546 (3)0.0609 (6)
H6A−0.04490.11010.62230.073*
C70.03355 (16)0.05664 (7)0.7976 (3)0.0598 (6)
H7A−0.01850.07020.81650.072*
C80.09664 (17)0.05217 (7)0.9066 (3)0.0629 (6)
H8A0.14670.03700.88700.075*
C90.08822 (15)0.06818 (7)1.0333 (3)0.0637 (6)
H9A0.03740.08291.05160.076*
C100.15066 (15)0.06500 (7)1.1471 (3)0.0588 (6)
C110.22801 (16)0.04272 (7)1.1346 (3)0.0669 (6)
H11A0.24170.03011.05020.080*
C120.28461 (18)0.03901 (9)1.2443 (3)0.0771 (8)
H12A0.33610.02411.23370.093*
C130.2651 (2)0.05718 (9)1.3688 (3)0.0822 (8)
H13A0.30330.05471.44310.099*
C140.18916 (19)0.07916 (10)1.3845 (3)0.0829 (8)
H14A0.17580.09131.46970.099*
C150.13291 (17)0.08318 (8)1.2745 (3)0.0703 (7)
H15A0.08200.09841.28600.084*
N10.04738 (12)0.04246 (5)0.6758 (2)0.0584 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0562 (11)0.0430 (9)0.0576 (14)0.0011 (8)0.0025 (11)0.0017 (9)
C20.0626 (11)0.0412 (10)0.0584 (14)0.0000 (9)0.0012 (11)0.0017 (9)
C30.0792 (15)0.0510 (11)0.0622 (15)0.0019 (11)−0.0095 (13)−0.0006 (11)
C40.0809 (15)0.0638 (13)0.0725 (16)0.0109 (12)−0.0124 (14)0.0089 (12)
C50.0807 (15)0.0509 (11)0.0770 (18)0.0140 (11)0.0009 (15)0.0072 (12)
C60.0714 (13)0.0432 (9)0.0681 (15)0.0043 (9)0.0024 (13)−0.0018 (10)
C70.0649 (13)0.0496 (11)0.0648 (16)−0.0036 (10)−0.0008 (13)0.0007 (11)
C80.0707 (14)0.0538 (11)0.0641 (16)0.0005 (10)−0.0006 (12)−0.0019 (12)
C90.0645 (13)0.0638 (13)0.0627 (16)0.0013 (11)0.0043 (13)−0.0040 (12)
C100.0632 (13)0.0539 (11)0.0593 (14)−0.0054 (10)0.0053 (12)−0.0010 (10)
C110.0663 (14)0.0743 (14)0.0600 (16)0.0005 (11)0.0086 (12)0.0008 (12)
C120.0688 (15)0.0864 (18)0.076 (2)0.0019 (13)0.0035 (14)0.0137 (15)
C130.0814 (17)0.0908 (19)0.074 (2)−0.0112 (15)−0.0109 (17)0.0062 (16)
C140.100 (2)0.0861 (17)0.0621 (18)−0.0064 (16)−0.0005 (17)−0.0145 (15)
C150.0763 (15)0.0673 (13)0.0673 (17)0.0006 (12)0.0044 (14)−0.0112 (13)
N10.0707 (11)0.0445 (8)0.0599 (13)0.0019 (8)−0.0044 (10)−0.0029 (9)
Geometric parameters (Å, °) top
C1—C21.399 (3)C8—C91.327 (4)
C1—C61.400 (3)C8—H8A0.9300
C1—N11.410 (3)C9—C101.461 (3)
C2—C31.389 (3)C9—H9A0.9300
C2—C2i1.485 (4)C10—C151.383 (4)
C3—C41.390 (3)C10—C111.393 (3)
C3—H3A0.9300C11—C121.375 (4)
C4—C51.368 (4)C11—H11A0.9300
C4—H4A0.9300C12—C131.362 (4)
C5—C61.373 (4)C12—H12A0.9300
C5—H5A0.9300C13—C141.373 (4)
C6—H6A0.9300C13—H13A0.9300
C7—N11.273 (3)C14—C151.375 (4)
C7—C81.438 (4)C14—H14A0.9300
C7—H7A0.9300C15—H15A0.9300
C2—C1—C6119.1 (2)C7—C8—H8A117.8
C2—C1—N1118.93 (17)C8—C9—C10126.6 (2)
C6—C1—N1121.7 (2)C8—C9—H9A116.7
C3—C2—C1118.76 (18)C10—C9—H9A116.7
C3—C2—C2i118.52 (15)C15—C10—C11117.3 (2)
C1—C2—C2i122.67 (16)C15—C10—C9120.3 (2)
C2—C3—C4121.4 (2)C11—C10—C9122.4 (2)
C2—C3—H3A119.3C12—C11—C10121.5 (3)
C4—C3—H3A119.3C12—C11—H11A119.3
C5—C4—C3119.3 (3)C10—C11—H11A119.3
C5—C4—H4A120.4C13—C12—C11119.8 (3)
C3—C4—H4A120.4C13—C12—H12A120.1
C4—C5—C6120.6 (2)C11—C12—H12A120.1
C4—C5—H5A119.7C12—C13—C14120.1 (3)
C6—C5—H5A119.7C12—C13—H13A120.0
C5—C6—C1120.8 (2)C14—C13—H13A120.0
C5—C6—H6A119.6C13—C14—C15120.1 (3)
C1—C6—H6A119.6C13—C14—H14A119.9
N1—C7—C8121.5 (2)C15—C14—H14A119.9
N1—C7—H7A119.3C14—C15—C10121.2 (2)
C8—C7—H7A119.3C14—C15—H15A119.4
C9—C8—C7124.4 (2)C10—C15—H15A119.4
C9—C8—H8A117.8C7—N1—C1120.32 (19)
C6—C1—C2—C3−1.9 (3)C8—C9—C10—C15−179.7 (2)
N1—C1—C2—C3−175.9 (2)C8—C9—C10—C11−2.0 (4)
C6—C1—C2—C2i175.3 (2)C15—C10—C11—C12−0.2 (4)
N1—C1—C2—C2i1.4 (3)C9—C10—C11—C12−177.9 (2)
C1—C2—C3—C40.7 (3)C10—C11—C12—C130.4 (4)
C2i—C2—C3—C4−176.6 (2)C11—C12—C13—C140.0 (5)
C2—C3—C4—C50.8 (4)C12—C13—C14—C15−0.5 (5)
C3—C4—C5—C6−1.1 (4)C13—C14—C15—C100.7 (5)
C4—C5—C6—C1−0.1 (4)C11—C10—C15—C14−0.4 (4)
C2—C1—C6—C51.7 (3)C9—C10—C15—C14177.4 (2)
N1—C1—C6—C5175.4 (2)C8—C7—N1—C1−174.1 (2)
N1—C7—C8—C9176.2 (2)C2—C1—N1—C7−147.5 (2)
C7—C8—C9—C10−179.2 (2)C6—C1—N1—C738.7 (3)
Symmetry codes: (i) −x, −y, 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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Dehghanpour, S., Asadizadeh, S., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65. Submitted. [Please provide paper code]

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

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.

Westrip, S. P. (2009). publCIF. In preparation.