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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Jan 14;65(Pt 2):o307. doi: 10.1107/S1600536809000804

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

Saeed Dehghanpour a,*, Farzaneh Afshariazar a, Shan Gao b, Seik Weng Ng c
PMCID: PMC2968126  PMID: 21581916

Abstract

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

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 ▶). graphic file with name e-65-0o307-scheme1.jpg

Experimental

Crystal data

  • C30H24N2

  • M r = 412.51

  • Orthorhombic, Inline graphic

  • a = 15.4354 (12) Å

  • b = 31.783 (2) Å

  • c = 9.6188 (8) Å

  • V = 4718.8 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 295 (2) K

  • 0.27 × 0.21 × 0.16 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.982, T max = 0.989

  • 11331 measured reflections

  • 1427 independent reflections

  • 1021 reflections with I > 2σ(I)

  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034

  • wR(F 2) = 0.110

  • S = 1.07

  • 1427 reflections

  • 145 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000804/bt2848sup1.cif

e-65-0o307-sup1.cif (15.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000804/bt2848Isup2.hkl

e-65-0o307-Isup2.hkl (70.7KB, 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 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

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

Figures

Fig. 1.

Fig. 1.

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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).

Crystal data

C30H24N2 F(000) = 1744
Mr = 412.51 Dx = 1.161 Mg m−3
Orthorhombic, Fdd2 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d Cell parameters from 7049 reflections
a = 15.4354 (12) Å θ = 3.2–27.5°
b = 31.783 (2) Å µ = 0.07 mm−1
c = 9.6188 (8) Å T = 295 K
V = 4718.8 (6) Å3 Cuboid, light yellow
Z = 8 0.27 × 0.21 × 0.16 mm
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Data collection

Rigaku R-AXIS RAPID diffractometer 1427 independent reflections
Radiation source: fine-focus sealed tube 1021 reflections with I > 2σ(I)
graphite Rint = 0.029
Detector resolution: 10.000 pixels mm-1 θmax = 27.5°, θmin = 3.2°
ω scans h = −20→19
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) k = −41→41
Tmin = 0.982, Tmax = 0.989 l = −12→12
11331 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110 H-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 parameters Δρmax = 0.11 e Å−3
1 restraint Δρmin = −0.15 e Å−3
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Special details

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

x y z Uiso*/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 −0.0859 0.0097 0.2831 0.077*
C4 −0.11943 (16) 0.06833 (8) 0.3424 (3) 0.0724 (7)
H4A −0.1561 0.0739 0.2679 0.087*
C5 −0.10622 (16) 0.09796 (7) 0.4433 (3) 0.0695 (7)
H5A −0.1333 0.1240 0.4363 0.083*
C6 −0.05334 (14) 0.08962 (6) 0.5546 (3) 0.0609 (6)
H6A −0.0449 0.1101 0.6223 0.073*
C7 0.03355 (16) 0.05664 (7) 0.7976 (3) 0.0598 (6)
H7A −0.0185 0.0702 0.8165 0.072*
C8 0.09664 (17) 0.05217 (7) 0.9066 (3) 0.0629 (6)
H8A 0.1467 0.0370 0.8870 0.075*
C9 0.08822 (15) 0.06818 (7) 1.0333 (3) 0.0637 (6)
H9A 0.0374 0.0829 1.0516 0.076*
C10 0.15066 (15) 0.06500 (7) 1.1471 (3) 0.0588 (6)
C11 0.22801 (16) 0.04272 (7) 1.1346 (3) 0.0669 (6)
H11A 0.2417 0.0301 1.0502 0.080*
C12 0.28461 (18) 0.03901 (9) 1.2443 (3) 0.0771 (8)
H12A 0.3361 0.0241 1.2337 0.093*
C13 0.2651 (2) 0.05718 (9) 1.3688 (3) 0.0822 (8)
H13A 0.3033 0.0547 1.4431 0.099*
C14 0.18916 (19) 0.07916 (10) 1.3845 (3) 0.0829 (8)
H14A 0.1758 0.0913 1.4697 0.099*
C15 0.13291 (17) 0.08318 (8) 1.2745 (3) 0.0703 (7)
H15A 0.0820 0.0984 1.2860 0.084*
N1 0.04738 (12) 0.04246 (5) 0.6758 (2) 0.0584 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0562 (11) 0.0430 (9) 0.0576 (14) 0.0011 (8) 0.0025 (11) 0.0017 (9)
C2 0.0626 (11) 0.0412 (10) 0.0584 (14) 0.0000 (9) 0.0012 (11) 0.0017 (9)
C3 0.0792 (15) 0.0510 (11) 0.0622 (15) 0.0019 (11) −0.0095 (13) −0.0006 (11)
C4 0.0809 (15) 0.0638 (13) 0.0725 (16) 0.0109 (12) −0.0124 (14) 0.0089 (12)
C5 0.0807 (15) 0.0509 (11) 0.0770 (18) 0.0140 (11) 0.0009 (15) 0.0072 (12)
C6 0.0714 (13) 0.0432 (9) 0.0681 (15) 0.0043 (9) 0.0024 (13) −0.0018 (10)
C7 0.0649 (13) 0.0496 (11) 0.0648 (16) −0.0036 (10) −0.0008 (13) 0.0007 (11)
C8 0.0707 (14) 0.0538 (11) 0.0641 (16) 0.0005 (10) −0.0006 (12) −0.0019 (12)
C9 0.0645 (13) 0.0638 (13) 0.0627 (16) 0.0013 (11) 0.0043 (13) −0.0040 (12)
C10 0.0632 (13) 0.0539 (11) 0.0593 (14) −0.0054 (10) 0.0053 (12) −0.0010 (10)
C11 0.0663 (14) 0.0743 (14) 0.0600 (16) 0.0005 (11) 0.0086 (12) 0.0008 (12)
C12 0.0688 (15) 0.0864 (18) 0.076 (2) 0.0019 (13) 0.0035 (14) 0.0137 (15)
C13 0.0814 (17) 0.0908 (19) 0.074 (2) −0.0112 (15) −0.0109 (17) 0.0062 (16)
C14 0.100 (2) 0.0861 (17) 0.0621 (18) −0.0064 (16) −0.0005 (17) −0.0145 (15)
C15 0.0763 (15) 0.0673 (13) 0.0673 (17) 0.0006 (12) 0.0044 (14) −0.0112 (13)
N1 0.0707 (11) 0.0445 (8) 0.0599 (13) 0.0019 (8) −0.0044 (10) −0.0029 (9)
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Geometric parameters (Å, °)

C1—C2 1.399 (3) C8—C9 1.327 (4)
C1—C6 1.400 (3) C8—H8A 0.9300
C1—N1 1.410 (3) C9—C10 1.461 (3)
C2—C3 1.389 (3) C9—H9A 0.9300
C2—C2i 1.485 (4) C10—C15 1.383 (4)
C3—C4 1.390 (3) C10—C11 1.393 (3)
C3—H3A 0.9300 C11—C12 1.375 (4)
C4—C5 1.368 (4) C11—H11A 0.9300
C4—H4A 0.9300 C12—C13 1.362 (4)
C5—C6 1.373 (4) C12—H12A 0.9300
C5—H5A 0.9300 C13—C14 1.373 (4)
C6—H6A 0.9300 C13—H13A 0.9300
C7—N1 1.273 (3) C14—C15 1.375 (4)
C7—C8 1.438 (4) C14—H14A 0.9300
C7—H7A 0.9300 C15—H15A 0.9300
C2—C1—C6 119.1 (2) C7—C8—H8A 117.8
C2—C1—N1 118.93 (17) C8—C9—C10 126.6 (2)
C6—C1—N1 121.7 (2) C8—C9—H9A 116.7
C3—C2—C1 118.76 (18) C10—C9—H9A 116.7
C3—C2—C2i 118.52 (15) C15—C10—C11 117.3 (2)
C1—C2—C2i 122.67 (16) C15—C10—C9 120.3 (2)
C2—C3—C4 121.4 (2) C11—C10—C9 122.4 (2)
C2—C3—H3A 119.3 C12—C11—C10 121.5 (3)
C4—C3—H3A 119.3 C12—C11—H11A 119.3
C5—C4—C3 119.3 (3) C10—C11—H11A 119.3
C5—C4—H4A 120.4 C13—C12—C11 119.8 (3)
C3—C4—H4A 120.4 C13—C12—H12A 120.1
C4—C5—C6 120.6 (2) C11—C12—H12A 120.1
C4—C5—H5A 119.7 C12—C13—C14 120.1 (3)
C6—C5—H5A 119.7 C12—C13—H13A 120.0
C5—C6—C1 120.8 (2) C14—C13—H13A 120.0
C5—C6—H6A 119.6 C13—C14—C15 120.1 (3)
C1—C6—H6A 119.6 C13—C14—H14A 119.9
N1—C7—C8 121.5 (2) C15—C14—H14A 119.9
N1—C7—H7A 119.3 C14—C15—C10 121.2 (2)
C8—C7—H7A 119.3 C14—C15—H15A 119.4
C9—C8—C7 124.4 (2) C10—C15—H15A 119.4
C9—C8—H8A 117.8 C7—N1—C1 120.32 (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—C2i 175.3 (2) C15—C10—C11—C12 −0.2 (4)
N1—C1—C2—C2i 1.4 (3) C9—C10—C11—C12 −177.9 (2)
C1—C2—C3—C4 0.7 (3) C10—C11—C12—C13 0.4 (4)
C2i—C2—C3—C4 −176.6 (2) C11—C12—C13—C14 0.0 (5)
C2—C3—C4—C5 0.8 (4) C12—C13—C14—C15 −0.5 (5)
C3—C4—C5—C6 −1.1 (4) C13—C14—C15—C10 0.7 (5)
C4—C5—C6—C1 −0.1 (4) C11—C10—C15—C14 −0.4 (4)
C2—C1—C6—C5 1.7 (3) C9—C10—C15—C14 177.4 (2)
N1—C1—C6—C5 175.4 (2) C8—C7—N1—C1 −174.1 (2)
N1—C7—C8—C9 176.2 (2) C2—C1—N1—C7 −147.5 (2)
C7—C8—C9—C10 −179.2 (2) C6—C1—N1—C7 38.7 (3)
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Symmetry codes: (i) −x, −y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2848).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Dehghanpour, S., Asadizadeh, S., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, o306. [DOI] [PMC free article] [PubMed]
  3. Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  4. Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  5. Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000804/bt2848sup1.cif

e-65-0o307-sup1.cif (15.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000804/bt2848Isup2.hkl

e-65-0o307-Isup2.hkl (70.7KB, hkl)

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

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

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