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accessBiphenyl-4-carbaldehyde azine
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The complete molecule of the title compound, C26H20N2, is generated by crystallographic inversion symmetry. The terminal phenyl ring is twisted by 19.2 (1)° with respect to the adjacent phenylene ring.
Related literature
For the synthesis, see: Malkes & Timchenko (1961![[Malkes, L. Ya. & Timchenko, A. I. (1961). Zh. Obshch. Khim. 31, 560-562.]](../../../../../../logos/arrows/e_arr.gif "Malkes, L. Ya. & Timchenko, A. I. (1961). Zh. Obshch. Khim. 31, 560-562.")
). For biological evaluation, see: Cremlyn et al. (1991). The compound is a formylating agent for aromatic compounds; see: Kantlehner et al. (2004). When treated with cerium ammonium nitrate, the aldehyde is regenerated; see Giurg & Mlochowski (1999).
![[Scheme 1]](hb2856scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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, 2008).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808038622/hb2856sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808038622/hb2856Isup2.hkl
4-Phenyl benzaldehyde (0.72 g, 4 mmol) and 80% hydrazine hydrate (0.10 g, 2 mmol) were heated in ethanol (25 ml) for 1 h. The resulting product was filtered and washed with ethanol and then recrystallized from hexane to yield yellow prisms of (I).
The H atoms were placed in calculated positions (C—H = 0.95 Å) and refined as riding with U(H) = 1.2U(C).
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).
![[Figure 1]](./hb2856fig1thm.gif) | Fig. 1. The molecular structure of (I) with atoms shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius. The unlabelled atoms are generated by the symmetry operation (1–x, 1–y, 1–z). |
| C26H20N2 | F(000) = 380 |
| Mr = 360.44 | Dx = 1.291 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1869 reflections |
| a = 20.5417 (6) Å | θ = 2.9–26.2° |
| b = 7.1358 (2) Å | µ = 0.08 mm−1 |
| c = 6.3402 (2) Å | T = 100 K |
| β = 93.632 (2)° | Prism, yellow |
| V = 927.49 (5) Å3 | 0.40 × 0.25 × 0.10 mm |
| Z = 2 |
| Bruker SMART APEX CCD diffractometer | 1607 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.025 |
| Graphite monochromator | θmax = 27.5°, θmin = 1.0° |
| ω scans | h = −25→26 |
| 6044 measured reflections | k = −8→9 |
| 2104 independent reflections | l = −8→8 |
| 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2493P] where P = (Fo2 + 2Fc2)/3 |
| 2104 reflections | (Δ/σ)max = 0.001 |
| 127 parameters | Δρmax = 0.31 e Å−3 |
| 0 restraints | Δρmin = −0.21 e Å−3 |
| C26H20N2 | V = 927.49 (5) Å3 |
| Mr = 360.44 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 20.5417 (6) Å | µ = 0.08 mm−1 |
| b = 7.1358 (2) Å | T = 100 K |
| c = 6.3402 (2) Å | 0.40 × 0.25 × 0.10 mm |
| β = 93.632 (2)° |
| Bruker SMART APEX CCD diffractometer | 1607 reflections with I > 2σ(I) |
| 6044 measured reflections | Rint = 0.025 |
| 2104 independent reflections |
| R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.31 e Å−3 |
| 2104 reflections | Δρmin = −0.21 e Å−3 |
| 127 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.46654 (6) | 0.48506 (18) | 0.47390 (19) | 0.0260 (3) | |
| C1 | 0.45139 (7) | 0.5211 (2) | 0.2795 (2) | 0.0229 (3) | |
| H1 | 0.4847 | 0.5598 | 0.1916 | 0.027* | |
| C2 | 0.38464 (7) | 0.50463 (19) | 0.1880 (2) | 0.0202 (3) | |
| C3 | 0.37032 (7) | 0.5594 (2) | −0.0206 (2) | 0.0218 (3) | |
| H3 | 0.4045 | 0.6006 | −0.1034 | 0.026* | |
| C4 | 0.30685 (7) | 0.5548 (2) | −0.1095 (2) | 0.0205 (3) | |
| H4 | 0.2983 | 0.5927 | −0.2522 | 0.025* | |
| C5 | 0.25534 (6) | 0.49541 (19) | 0.0078 (2) | 0.0169 (3) | |
| C6 | 0.27039 (7) | 0.43846 (19) | 0.2177 (2) | 0.0198 (3) | |
| H6 | 0.2363 | 0.3972 | 0.3008 | 0.024* | |
| C7 | 0.33352 (7) | 0.4412 (2) | 0.3054 (2) | 0.0212 (3) | |
| H7 | 0.3424 | 0.3998 | 0.4467 | 0.025* | |
| C8 | 0.18693 (6) | 0.49529 (18) | −0.08434 (19) | 0.0170 (3) | |
| C9 | 0.16848 (7) | 0.60293 (19) | −0.2631 (2) | 0.0202 (3) | |
| H9 | 0.2005 | 0.6745 | −0.3287 | 0.024* | |
| C10 | 0.10445 (7) | 0.6072 (2) | −0.3461 (2) | 0.0215 (3) | |
| H10 | 0.0932 | 0.6811 | −0.4676 | 0.026* | |
| C11 | 0.05681 (7) | 0.5041 (2) | −0.2529 (2) | 0.0200 (3) | |
| H11 | 0.0128 | 0.5083 | −0.3084 | 0.024* | |
| C12 | 0.07425 (6) | 0.39455 (19) | −0.0772 (2) | 0.0197 (3) | |
| H12 | 0.0420 | 0.3224 | −0.0132 | 0.024* | |
| C13 | 0.13839 (6) | 0.38970 (19) | 0.0054 (2) | 0.0186 (3) | |
| H13 | 0.1496 | 0.3133 | 0.1249 | 0.022* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0154 (6) | 0.0334 (7) | 0.0285 (7) | −0.0007 (5) | −0.0034 (5) | −0.0004 (5) |
| C1 | 0.0174 (7) | 0.0249 (8) | 0.0261 (7) | 0.0009 (5) | −0.0003 (5) | −0.0009 (6) |
| C2 | 0.0171 (7) | 0.0195 (7) | 0.0235 (7) | 0.0013 (5) | −0.0018 (5) | −0.0020 (5) |
| C3 | 0.0181 (7) | 0.0244 (7) | 0.0231 (7) | −0.0002 (5) | 0.0028 (5) | 0.0015 (5) |
| C4 | 0.0205 (7) | 0.0229 (7) | 0.0178 (6) | 0.0009 (5) | 0.0002 (5) | 0.0015 (5) |
| C5 | 0.0168 (7) | 0.0149 (6) | 0.0187 (6) | 0.0012 (5) | −0.0017 (5) | −0.0015 (5) |
| C6 | 0.0188 (7) | 0.0209 (7) | 0.0196 (6) | −0.0007 (5) | 0.0013 (5) | 0.0015 (5) |
| C7 | 0.0221 (7) | 0.0225 (7) | 0.0186 (6) | 0.0005 (5) | −0.0020 (5) | 0.0007 (5) |
| C8 | 0.0185 (7) | 0.0164 (6) | 0.0160 (6) | 0.0012 (5) | −0.0010 (5) | −0.0028 (5) |
| C9 | 0.0203 (7) | 0.0201 (7) | 0.0200 (6) | −0.0024 (5) | 0.0000 (5) | 0.0025 (5) |
| C10 | 0.0245 (7) | 0.0213 (7) | 0.0182 (6) | 0.0011 (5) | −0.0036 (5) | 0.0020 (5) |
| C11 | 0.0170 (7) | 0.0227 (7) | 0.0197 (6) | 0.0018 (5) | −0.0037 (5) | −0.0036 (5) |
| C12 | 0.0185 (7) | 0.0210 (7) | 0.0196 (6) | −0.0016 (5) | 0.0022 (5) | −0.0010 (5) |
| C13 | 0.0195 (7) | 0.0191 (7) | 0.0169 (6) | 0.0008 (5) | −0.0004 (5) | 0.0010 (5) |
| N1—C1 | 1.2784 (19) | C6—H6 | 0.9500 |
| N1—N1i | 1.410 (2) | C7—H7 | 0.9500 |
| C1—C2 | 1.4592 (18) | C8—C13 | 1.3989 (18) |
| C1—H1 | 0.9500 | C8—C9 | 1.4012 (18) |
| C2—C3 | 1.3927 (18) | C9—C10 | 1.3858 (19) |
| C2—C7 | 1.4006 (19) | C9—H9 | 0.9500 |
| C3—C4 | 1.3874 (18) | C10—C11 | 1.3863 (19) |
| C3—H3 | 0.9500 | C10—H10 | 0.9500 |
| C4—C5 | 1.3969 (19) | C11—C12 | 1.3888 (19) |
| C4—H4 | 0.9500 | C11—H11 | 0.9500 |
| C5—C6 | 1.4073 (18) | C12—C13 | 1.3870 (18) |
| C5—C8 | 1.4873 (17) | C12—H12 | 0.9500 |
| C6—C7 | 1.3784 (18) | C13—H13 | 0.9500 |
| C1—N1—N1i | 111.73 (15) | C6—C7—H7 | 119.7 |
| N1—C1—C2 | 122.17 (13) | C2—C7—H7 | 119.7 |
| N1—C1—H1 | 118.9 | C13—C8—C9 | 117.44 (12) |
| C2—C1—H1 | 118.9 | C13—C8—C5 | 121.38 (11) |
| C3—C2—C7 | 118.38 (12) | C9—C8—C5 | 121.17 (12) |
| C3—C2—C1 | 119.45 (13) | C10—C9—C8 | 121.38 (12) |
| C7—C2—C1 | 122.14 (12) | C10—C9—H9 | 119.3 |
| C4—C3—C2 | 121.03 (12) | C8—C9—H9 | 119.3 |
| C4—C3—H3 | 119.5 | C9—C10—C11 | 120.34 (12) |
| C2—C3—H3 | 119.5 | C9—C10—H10 | 119.8 |
| C3—C4—C5 | 121.01 (12) | C11—C10—H10 | 119.8 |
| C3—C4—H4 | 119.5 | C10—C11—C12 | 119.17 (12) |
| C5—C4—H4 | 119.5 | C10—C11—H11 | 120.4 |
| C4—C5—C6 | 117.55 (12) | C12—C11—H11 | 120.4 |
| C4—C5—C8 | 121.34 (11) | C13—C12—C11 | 120.49 (13) |
| C6—C5—C8 | 121.11 (12) | C13—C12—H12 | 119.8 |
| C7—C6—C5 | 121.48 (12) | C11—C12—H12 | 119.8 |
| C7—C6—H6 | 119.3 | C12—C13—C8 | 121.16 (12) |
| C5—C6—H6 | 119.3 | C12—C13—H13 | 119.4 |
| C6—C7—C2 | 120.53 (12) | C8—C13—H13 | 119.4 |
| N1i—N1—C1—C2 | −178.70 (14) | C4—C5—C8—C13 | 161.70 (13) |
| N1—C1—C2—C3 | 175.14 (14) | C6—C5—C8—C13 | −19.36 (19) |
| N1—C1—C2—C7 | −2.6 (2) | C4—C5—C8—C9 | −19.07 (19) |
| C7—C2—C3—C4 | 1.2 (2) | C6—C5—C8—C9 | 159.86 (13) |
| C1—C2—C3—C4 | −176.66 (13) | C13—C8—C9—C10 | 0.99 (19) |
| C2—C3—C4—C5 | 0.1 (2) | C5—C8—C9—C10 | −178.27 (12) |
| C3—C4—C5—C6 | −0.8 (2) | C8—C9—C10—C11 | 0.1 (2) |
| C3—C4—C5—C8 | 178.21 (13) | C9—C10—C11—C12 | −0.9 (2) |
| C4—C5—C6—C7 | 0.1 (2) | C10—C11—C12—C13 | 0.7 (2) |
| C8—C5—C6—C7 | −178.86 (12) | C11—C12—C13—C8 | 0.5 (2) |
| C5—C6—C7—C2 | 1.2 (2) | C9—C8—C13—C12 | −1.26 (19) |
| C3—C2—C7—C6 | −1.8 (2) | C5—C8—C13—C12 | 177.99 (12) |
| C1—C2—C7—C6 | 175.96 (13) |
| Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | C26H20N2 |
| Mr | 360.44 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 20.5417 (6), 7.1358 (2), 6.3402 (2) |
| β (°) | 93.632 (2) |
| V (Å3) | 927.49 (5) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.08 |
| Crystal size (mm) | 0.40 × 0.25 × 0.10 |
| Data collection | |
| Diffractometer | Bruker SMART APEX CCD diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 6044, 2104, 1607 |
| Rint | 0.025 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.127, 1.06 |
| No. of reflections | 2104 |
| No. of parameters | 127 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.31, −0.21 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Acknowledgements
We thank the University of Malaya for supporting this study.
References
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The complete molecule of the title compound, (I) is generated by crystallographic inversion symmetry (Fig. 1). The terminal phenyl ring is twisted by 19.2 (1) ° with respect to the phenylene ring.