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 ▶); Coxall et al. (2003 ▶); Cunningham et al. (2004 ▶); Finder et al. (1973 ▶); Pruszynski et al. (1992 ▶).
Experimental
Crystal data
C26H18Br2N2
M r = 518.24
Orthorhombic,
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 ▶) 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 ▶), 1209 Friedel pairs
Flack parameter: −0.013 (15)
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/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
| C26H18Br2N2 | F(000) = 1032 |
| Mr = 518.24 | Dx = 1.539 Mg m−3 |
| Orthorhombic, Aba2 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: A 2 -2ac | Cell parameters from 5898 reflections |
| a = 15.9691 (10) Å | θ = 3.0–27.4° |
| b = 8.3482 (5) Å | µ = 3.64 mm−1 |
| c = 16.7767 (11) Å | T = 295 K |
| V = 2236.6 (2) Å3 | Cuboid, light yellow |
| Z = 4 | 0.28 × 0.25 × 0.19 mm |
Data collection
| Rigaku R-AXIS RAPID diffractometer | 2542 independent reflections |
| Radiation source: fine-focus sealed tube | 1333 reflections with I > 2σ(I) |
| graphite | Rint = 0.040 |
| Detector resolution: 10.000 pixels mm-1 | θmax = 27.4°, θmin = 3.0° |
| ω scans | h = −18→20 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→10 |
| Tmin = 0.429, Tmax = 0.545 | l = −21→21 |
| 10424 measured reflections |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.034 | H-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 reflections | Δρmax = 0.28 e Å−3 |
| 136 parameters | Δρmin = −0.36 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 1209 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: −0.013 (15) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.89090 (4) | 0.63217 (6) | 0.50003 (6) | 0.1058 (3) | |
| N1 | 0.8979 (2) | 1.3119 (4) | 0.7320 (3) | 0.0604 (9) | |
| C1 | 0.8877 (2) | 1.4642 (5) | 0.7689 (3) | 0.0555 (10) | |
| C2 | 0.9576 (2) | 1.5394 (4) | 0.8036 (2) | 0.0537 (9) | |
| C3 | 0.9461 (3) | 1.6846 (5) | 0.8415 (3) | 0.0650 (11) | |
| H3 | 0.9920 | 1.7371 | 0.8636 | 0.078* | |
| C4 | 0.8672 (3) | 1.7534 (6) | 0.8471 (4) | 0.0676 (13) | |
| H4 | 0.8605 | 1.8514 | 0.8727 | 0.081* | |
| C5 | 0.7989 (3) | 1.6768 (5) | 0.8150 (3) | 0.0685 (12) | |
| H5 | 0.7459 | 1.7214 | 0.8205 | 0.082* | |
| C6 | 0.8087 (2) | 1.5347 (5) | 0.7748 (3) | 0.0656 (12) | |
| H6 | 0.7626 | 1.4854 | 0.7514 | 0.079* | |
| C7 | 0.8654 (3) | 1.2832 (7) | 0.6649 (3) | 0.0633 (12) | |
| H7 | 0.8381 | 1.3663 | 0.6387 | 0.076* | |
| C8 | 0.8685 (3) | 1.1275 (5) | 0.6264 (3) | 0.0597 (11) | |
| C9 | 0.8443 (3) | 1.1094 (5) | 0.5480 (3) | 0.0818 (14) | |
| H9 | 0.8236 | 1.1973 | 0.5202 | 0.098* | |
| C10 | 0.8505 (3) | 0.9629 (6) | 0.5101 (4) | 0.0891 (14) | |
| H10 | 0.8346 | 0.9518 | 0.4570 | 0.107* | |
| C11 | 0.8805 (3) | 0.8339 (6) | 0.5523 (3) | 0.0714 (13) | |
| C12 | 0.9015 (3) | 0.8464 (5) | 0.6305 (3) | 0.0703 (13) | |
| H12 | 0.9195 | 0.7566 | 0.6585 | 0.084* | |
| C13 | 0.8961 (2) | 0.9926 (5) | 0.6683 (3) | 0.0646 (11) | |
| H13 | 0.9108 | 1.0016 | 0.7217 | 0.078* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.1445 (6) | 0.0704 (3) | 0.1026 (5) | −0.0098 (2) | 0.0284 (5) | −0.0131 (4) |
| N1 | 0.058 (2) | 0.0512 (18) | 0.072 (3) | −0.0048 (15) | 0.0000 (19) | −0.0029 (19) |
| C1 | 0.050 (3) | 0.058 (2) | 0.058 (3) | 0.0000 (18) | 0.0025 (18) | 0.009 (2) |
| C2 | 0.054 (2) | 0.052 (2) | 0.056 (2) | −0.0007 (16) | 0.0007 (19) | 0.0069 (19) |
| C3 | 0.063 (3) | 0.064 (2) | 0.067 (3) | −0.001 (2) | −0.005 (2) | −0.004 (2) |
| C4 | 0.081 (4) | 0.057 (3) | 0.065 (3) | 0.004 (2) | −0.002 (3) | −0.002 (2) |
| C5 | 0.059 (3) | 0.064 (2) | 0.082 (3) | 0.017 (2) | 0.008 (2) | 0.008 (2) |
| C6 | 0.052 (3) | 0.065 (3) | 0.080 (3) | −0.0025 (19) | 0.000 (2) | 0.014 (2) |
| C7 | 0.066 (3) | 0.066 (3) | 0.058 (3) | 0.000 (2) | −0.007 (2) | 0.010 (2) |
| C8 | 0.062 (2) | 0.065 (3) | 0.052 (3) | −0.0084 (18) | −0.002 (2) | 0.001 (2) |
| C9 | 0.111 (4) | 0.068 (3) | 0.066 (3) | 0.004 (3) | −0.020 (3) | 0.002 (2) |
| C10 | 0.127 (4) | 0.075 (3) | 0.066 (3) | −0.001 (3) | −0.024 (4) | 0.010 (3) |
| C11 | 0.065 (3) | 0.084 (3) | 0.065 (3) | −0.006 (2) | 0.008 (2) | 0.004 (3) |
| C12 | 0.070 (3) | 0.058 (2) | 0.083 (4) | −0.0047 (19) | −0.004 (3) | 0.015 (2) |
| C13 | 0.074 (3) | 0.060 (3) | 0.059 (3) | 0.001 (2) | −0.008 (2) | 0.006 (2) |
Geometric parameters (Å, °)
| Br1—C11 | 1.906 (5) | C6—H6 | 0.9300 |
| N1—C7 | 1.262 (6) | C7—C8 | 1.452 (7) |
| N1—C1 | 1.424 (6) | C7—H7 | 0.9300 |
| C1—C6 | 1.395 (5) | C8—C9 | 1.378 (7) |
| C1—C2 | 1.407 (6) | C8—C13 | 1.399 (6) |
| C2—C3 | 1.381 (6) | C9—C10 | 1.383 (6) |
| C2—C2i | 1.506 (7) | C9—H9 | 0.9300 |
| C3—C4 | 1.389 (6) | C10—C11 | 1.376 (7) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.373 (7) | C11—C12 | 1.358 (8) |
| C4—H4 | 0.9300 | C12—C13 | 1.378 (6) |
| C5—C6 | 1.374 (6) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | C13—H13 | 0.9300 |
| C7—N1—C1 | 120.7 (4) | N1—C7—H7 | 118.2 |
| C6—C1—C2 | 120.0 (4) | C8—C7—H7 | 118.2 |
| C6—C1—N1 | 120.8 (4) | C9—C8—C13 | 118.6 (4) |
| C2—C1—N1 | 119.2 (3) | C9—C8—C7 | 120.9 (4) |
| C3—C2—C1 | 118.5 (4) | C13—C8—C7 | 120.5 (5) |
| C3—C2—C2i | 120.2 (4) | C8—C9—C10 | 121.1 (4) |
| C1—C2—C2i | 121.2 (4) | C8—C9—H9 | 119.5 |
| C2—C3—C4 | 121.0 (4) | C10—C9—H9 | 119.5 |
| C2—C3—H3 | 119.5 | C9—C10—C11 | 118.7 (5) |
| C4—C3—H3 | 119.5 | C9—C10—H10 | 120.7 |
| C5—C4—C3 | 120.1 (4) | C11—C10—H10 | 120.7 |
| C5—C4—H4 | 120.0 | C12—C11—C10 | 121.6 (5) |
| C3—C4—H4 | 120.0 | C12—C11—Br1 | 119.4 (4) |
| C6—C5—C4 | 120.3 (4) | C10—C11—Br1 | 119.0 (4) |
| C6—C5—H5 | 119.8 | C11—C12—C13 | 119.8 (5) |
| C4—C5—H5 | 119.8 | C11—C12—H12 | 120.1 |
| C5—C6—C1 | 120.1 (4) | C13—C12—H12 | 120.1 |
| C5—C6—H6 | 119.9 | C12—C13—C8 | 120.1 (5) |
| C1—C6—H6 | 119.9 | C12—C13—H13 | 119.9 |
| N1—C7—C8 | 123.6 (5) | C8—C13—H13 | 119.9 |
| C7—N1—C1—C6 | 48.5 (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—C13 | 10.8 (7) |
| N1—C1—C2—C3 | −177.9 (4) | C13—C8—C9—C10 | −2.8 (8) |
| C6—C1—C2—C2i | 175.4 (3) | C7—C8—C9—C10 | 177.2 (5) |
| N1—C1—C2—C2i | −1.1 (5) | C8—C9—C10—C11 | 0.6 (8) |
| C1—C2—C3—C4 | 1.6 (6) | C9—C10—C11—C12 | 2.1 (7) |
| C2i—C2—C3—C4 | −175.3 (4) | C9—C10—C11—Br1 | −179.0 (4) |
| C2—C3—C4—C5 | 0.2 (8) | C10—C11—C12—C13 | −2.7 (7) |
| C3—C4—C5—C6 | −2.2 (8) | Br1—C11—C12—C13 | 178.5 (3) |
| C4—C5—C6—C1 | 2.4 (7) | C11—C12—C13—C8 | 0.4 (7) |
| C2—C1—C6—C5 | −0.6 (7) | C9—C8—C13—C12 | 2.2 (7) |
| N1—C1—C6—C5 | 175.9 (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. [DOI] [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. [DOI] [PubMed]
- 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/S1600536809000993/tk2356sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000993/tk2356Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report