organic compounds
A new crystal phase of N,N,N′,N′-tetraphenyl-1,1′-biphenyl-4,4′-diamine
aDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8570, Japan, and bRigaku Co., Akishima, Tokyo 196-8666, Japan
*Correspondence e-mail: toyonari@c.s.osakafu-u.ac.jp
The complete molecule of the title compound, C36H28N2, is generated by a crystallographic centre of inversion. The biphenyl unit is forced by symmetry to be essentially flat (r.m.s. deviation = 0.008 Å); the dihedral angles between it and the two terminal phenyl rings are 69.39 (5) and 59.53 (5)°.
Related literature
For the electronic properties of semiconductors based triarylamines, see, for example: Kennedy et al. (2002); Shirota (2000, 2005); Song et al. (2006). For the preparation of triarylamine, see: Hartwig (1999). For related structures, see: Kennedy et al. (2002); Low et al. (2004); Zhang et al. (2004, 2006).
Experimental
Crystal data
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536809016389/bq2132sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809016389/bq2132Isup2.hkl
A suspension of 4,4'-dibromobiphenyl (3.1 g, 10 mmol), diphenylamine (3.9 g, 21 mmol) and sodium t-butoxide (2.3 g, 24 mmol) in xylene (20 ml) was refluxed in the presence of palladium(II) acetate (4.4 mg, 0.020 mmol) and triphenylphosphine (42 mg, 0.016 mmol) for 5 h under an argon atmosphere. After removing the solvent in vacuum, the residue was separated by
on silica gel using benzene as to afford the title compound in the yield of 71%. The single crystals of (I) suitable for the X-ray crystallographic analysis were obtained by recrystallization from benzene/hexane as colorless blocks.All of the H atoms were positioned geometrically with C–H of 0.95Å and were constrained in a riding motion on their parent carbon atoms with Uiso(H) = 1.2 Ueq(C).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2007).C36H28N2 | F(000) = 516.00 |
Mr = 488.63 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/n | Melting point: 400 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54187 Å |
a = 9.6846 (2) Å | Cell parameters from 9402 reflections |
b = 14.2661 (4) Å | θ = 4.7–68.2° |
c = 9.7946 (2) Å | µ = 0.56 mm−1 |
β = 107.0521 (15)° | T = 173 K |
V = 1293.75 (5) Å3 | Block, colorless |
Z = 2 | 0.15 × 0.14 × 0.11 mm |
Rigaku R-AXIS RAPID diffractometer | 1956 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.045 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.885, Tmax = 0.941 | k = −17→16 |
14609 measured reflections | l = −11→11 |
2362 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0708P)2 + 0.1003P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.22 e Å−3 |
2362 reflections | Δρmin = −0.15 e Å−3 |
174 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008) |
0 restraints | Extinction coefficient: 0.0044 (7) |
C36H28N2 | V = 1293.75 (5) Å3 |
Mr = 488.63 | Z = 2 |
Monoclinic, P21/n | Cu Kα radiation |
a = 9.6846 (2) Å | µ = 0.56 mm−1 |
b = 14.2661 (4) Å | T = 173 K |
c = 9.7946 (2) Å | 0.15 × 0.14 × 0.11 mm |
β = 107.0521 (15)° |
Rigaku R-AXIS RAPID diffractometer | 2362 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1956 reflections with F2 > 2σ(F2) |
Tmin = 0.885, Tmax = 0.941 | Rint = 0.045 |
14609 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.22 e Å−3 |
2362 reflections | Δρmin = −0.15 e Å−3 |
174 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.61552 (11) | 0.35882 (8) | 0.48812 (11) | 0.0350 (3) | |
C1 | 0.75255 (14) | 0.38277 (9) | 0.58558 (13) | 0.0322 (3) | |
C2 | 0.76352 (16) | 0.41058 (10) | 0.72442 (14) | 0.0407 (3) | |
C3 | 0.89748 (16) | 0.43064 (10) | 0.81905 (15) | 0.0460 (4) | |
C4 | 1.02051 (16) | 0.42680 (10) | 0.77599 (16) | 0.0435 (3) | |
C5 | 1.00977 (15) | 0.40187 (10) | 0.63705 (16) | 0.0419 (3) | |
C6 | 0.87666 (15) | 0.37871 (9) | 0.54238 (15) | 0.0375 (3) | |
C7 | 0.52193 (14) | 0.29751 (9) | 0.53277 (13) | 0.0312 (3) | |
C8 | 0.57988 (15) | 0.22955 (9) | 0.63602 (13) | 0.0364 (3) | |
C9 | 0.49026 (15) | 0.17243 (10) | 0.68654 (14) | 0.0408 (3) | |
C10 | 0.34163 (15) | 0.17989 (10) | 0.63263 (14) | 0.0406 (3) | |
C11 | 0.28345 (15) | 0.24546 (10) | 0.52752 (14) | 0.0370 (3) | |
C12 | 0.37225 (14) | 0.30446 (9) | 0.47834 (13) | 0.0329 (3) | |
C13 | 0.57704 (13) | 0.39859 (9) | 0.34918 (13) | 0.0303 (3) | |
C14 | 0.61838 (14) | 0.48974 (9) | 0.33017 (13) | 0.0333 (3) | |
C15 | 0.58792 (14) | 0.52884 (9) | 0.19522 (13) | 0.0322 (3) | |
C16 | 0.51417 (12) | 0.47929 (9) | 0.07275 (12) | 0.0286 (3) | |
C17 | 0.46985 (14) | 0.38858 (9) | 0.09424 (13) | 0.0338 (3) | |
C18 | 0.50099 (14) | 0.34835 (9) | 0.22831 (13) | 0.0344 (3) | |
H2 | 0.6790 | 0.4158 | 0.7544 | 0.049* | |
H3 | 0.9045 | 0.4473 | 0.9148 | 0.055* | |
H4 | 1.1119 | 0.4412 | 0.8413 | 0.052* | |
H5 | 1.0939 | 0.4006 | 0.6060 | 0.050* | |
H6 | 0.8706 | 0.3600 | 0.4477 | 0.045* | |
H8 | 0.6817 | 0.2224 | 0.6719 | 0.044* | |
H9 | 0.5311 | 0.1277 | 0.7589 | 0.049* | |
H10 | 0.2804 | 0.1405 | 0.6674 | 0.049* | |
H11 | 0.1816 | 0.2501 | 0.4886 | 0.044* | |
H12 | 0.3308 | 0.3498 | 0.4072 | 0.039* | |
H14 | 0.6684 | 0.5258 | 0.4111 | 0.040* | |
H15 | 0.6181 | 0.5912 | 0.1857 | 0.039* | |
H17 | 0.4164 | 0.3533 | 0.0138 | 0.041* | |
H18 | 0.4704 | 0.2861 | 0.2382 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0320 (6) | 0.0420 (6) | 0.0280 (5) | −0.0078 (4) | 0.0041 (4) | 0.0056 (4) |
C1 | 0.0307 (7) | 0.0328 (7) | 0.0304 (6) | −0.0044 (5) | 0.0049 (5) | 0.0059 (4) |
C2 | 0.0374 (7) | 0.0514 (8) | 0.0347 (7) | −0.0094 (6) | 0.0125 (6) | −0.0006 (6) |
C3 | 0.0506 (9) | 0.0517 (9) | 0.0323 (7) | −0.0171 (7) | 0.0066 (6) | −0.0038 (6) |
C4 | 0.0349 (7) | 0.0412 (8) | 0.0461 (8) | −0.0087 (6) | −0.0010 (6) | 0.0025 (6) |
C5 | 0.0311 (7) | 0.0400 (7) | 0.0550 (9) | 0.0004 (5) | 0.0132 (6) | 0.0030 (6) |
C6 | 0.0370 (8) | 0.0406 (7) | 0.0343 (7) | 0.0005 (5) | 0.0097 (5) | 0.0019 (5) |
C7 | 0.0328 (7) | 0.0333 (7) | 0.0272 (6) | −0.0060 (5) | 0.0083 (5) | −0.0003 (4) |
C8 | 0.0328 (7) | 0.0389 (7) | 0.0342 (7) | −0.0043 (5) | 0.0047 (5) | 0.0034 (5) |
C9 | 0.0468 (8) | 0.0386 (7) | 0.0339 (7) | −0.0088 (6) | 0.0069 (6) | 0.0057 (5) |
C10 | 0.0450 (8) | 0.0430 (8) | 0.0365 (7) | −0.0138 (6) | 0.0162 (6) | −0.0024 (5) |
C11 | 0.0315 (7) | 0.0451 (8) | 0.0354 (7) | −0.0055 (5) | 0.0112 (5) | −0.0064 (5) |
C12 | 0.0342 (7) | 0.0346 (7) | 0.0295 (6) | −0.0010 (5) | 0.0086 (5) | −0.0015 (5) |
C13 | 0.0280 (6) | 0.0353 (7) | 0.0273 (6) | 0.0001 (5) | 0.0078 (5) | 0.0038 (4) |
C14 | 0.0353 (7) | 0.0330 (7) | 0.0290 (6) | −0.0020 (5) | 0.0052 (5) | −0.0014 (5) |
C15 | 0.0345 (7) | 0.0287 (6) | 0.0323 (6) | −0.0013 (5) | 0.0081 (5) | 0.0014 (4) |
C16 | 0.0231 (6) | 0.0322 (6) | 0.0307 (6) | 0.0034 (4) | 0.0081 (5) | 0.0015 (4) |
C17 | 0.0346 (7) | 0.0367 (7) | 0.0284 (6) | −0.0051 (5) | 0.0064 (5) | −0.0012 (5) |
C18 | 0.0375 (7) | 0.0324 (7) | 0.0328 (6) | −0.0060 (5) | 0.0096 (5) | 0.0021 (5) |
N1—C1 | 1.4304 (14) | C15—C16 | 1.3951 (16) |
N1—C7 | 1.4178 (18) | C16—C16i | 1.4920 (16) |
N1—C13 | 1.4196 (16) | C16—C17 | 1.3986 (18) |
C1—C2 | 1.3904 (19) | C17—C18 | 1.3829 (17) |
C1—C6 | 1.388 (2) | C2—H2 | 0.950 |
C2—C3 | 1.3852 (18) | C3—H3 | 0.950 |
C3—C4 | 1.377 (2) | C4—H4 | 0.950 |
C4—C5 | 1.381 (2) | C5—H5 | 0.950 |
C5—C6 | 1.3892 (17) | C6—H6 | 0.950 |
C7—C8 | 1.3946 (17) | C8—H8 | 0.950 |
C7—C12 | 1.3936 (17) | C9—H9 | 0.950 |
C8—C9 | 1.384 (2) | C10—H10 | 0.950 |
C9—C10 | 1.3843 (19) | C11—H11 | 0.950 |
C10—C11 | 1.3828 (18) | C12—H12 | 0.950 |
C11—C12 | 1.387 (2) | C14—H14 | 0.950 |
C13—C14 | 1.3891 (18) | C15—H15 | 0.950 |
C13—C18 | 1.3951 (16) | C17—H17 | 0.950 |
C14—C15 | 1.3844 (17) | C18—H18 | 0.950 |
C4···C9ii | 3.528 (2) | C14···H5vi | 3.095 |
C12···C14iii | 3.4707 (18) | C14···H10viii | 3.150 |
N1···H14iii | 3.582 | C14···H12iii | 3.370 |
C1···H18iv | 3.262 | C15···H2iii | 2.881 |
C2···H18iv | 3.427 | C15···H4vi | 3.061 |
C3···H3v | 3.252 | C15···H5vi | 3.283 |
C3···H9ii | 3.045 | C15···H10viii | 3.111 |
C3···H18iv | 3.319 | C16···H2iii | 3.235 |
C4···H3v | 3.412 | C16···H10viii | 3.004 |
C4···H9ii | 2.912 | C17···H8ix | 3.482 |
C4···H10ii | 3.562 | C17···H10viii | 2.910 |
C4···H15vi | 3.418 | C17···H11viii | 3.230 |
C4···H18iv | 3.081 | C18···H8ix | 3.144 |
C5···H9ii | 3.436 | C18···H10viii | 2.941 |
C5···H11vii | 3.315 | C18···H11viii | 3.599 |
C5···H14vi | 3.445 | H2···H11iv | 3.291 |
C5···H15vi | 3.513 | H2···H14iii | 3.382 |
C5···H18iv | 2.922 | H2···H15iii | 3.102 |
C6···H5vi | 3.515 | H3···H3v | 2.581 |
C6···H9viii | 3.520 | H3···H4v | 2.914 |
C6···H10viii | 3.525 | H3···H9ii | 3.245 |
C6···H17iv | 3.353 | H3···H9iv | 3.404 |
C6···H18iv | 3.001 | H3···H10iv | 3.298 |
C7···H14iii | 3.263 | H4···H9ii | 3.027 |
C8···H3ix | 3.433 | H4···H10ii | 3.038 |
C8···H11iv | 3.314 | H4···H15vi | 2.743 |
C8···H12iv | 3.234 | H4···H17xiii | 3.194 |
C9···H3x | 3.597 | H4···H18iv | 3.549 |
C9···H3ix | 3.065 | H5···H6vi | 3.488 |
C9···H4x | 3.432 | H5···H9viii | 3.298 |
C9···H6xi | 3.137 | H5···H11vii | 2.687 |
C9···H11iv | 3.192 | H5···H12vii | 3.493 |
C9···H12iv | 3.387 | H5···H14vi | 2.580 |
C10···H3ix | 2.996 | H5···H15vi | 2.935 |
C10···H4x | 3.435 | H5···H18iv | 3.332 |
C10···H6xi | 3.069 | H6···H9viii | 2.748 |
C11···H2ix | 3.447 | H6···H10viii | 2.626 |
C11···H3ix | 3.303 | H6···H11vii | 3.314 |
C11···H5xii | 3.112 | H6···H17iv | 3.116 |
C11···H8ix | 3.361 | H6···H18iv | 3.429 |
C11···H9ix | 3.521 | H8···H11iv | 3.127 |
C11···H14iii | 3.326 | H8···H12iv | 2.551 |
C11···H15iii | 3.557 | H8···H17iv | 3.286 |
C12···H5xii | 3.562 | H8···H18iv | 2.682 |
C12···H8ix | 3.052 | H9···H11iv | 2.881 |
C12···H9ix | 3.508 | H9···H12iv | 2.857 |
C12···H14iii | 2.728 | H10···H17xi | 3.404 |
C12···H15iii | 3.587 | H10···H18xi | 3.437 |
C13···H2iii | 3.566 | H11···H14iii | 3.529 |
C13···H10viii | 3.068 | H11···H17xi | 3.034 |
C14···H2iii | 3.066 | H12···H14iii | 2.511 |
C1—N1—C7 | 119.56 (10) | C1—C2—H2 | 120.0 |
C1—N1—C13 | 118.40 (10) | C3—C2—H2 | 120.0 |
C7—N1—C13 | 122.03 (9) | C2—C3—H3 | 119.6 |
N1—C1—C2 | 120.71 (13) | C4—C3—H3 | 119.6 |
N1—C1—C6 | 120.24 (11) | C3—C4—H4 | 120.3 |
C2—C1—C6 | 119.05 (11) | C5—C4—H4 | 120.3 |
C1—C2—C3 | 120.09 (14) | C4—C5—H5 | 119.8 |
C2—C3—C4 | 120.78 (13) | C6—C5—H5 | 119.8 |
C3—C4—C5 | 119.37 (12) | C1—C6—H6 | 119.9 |
C4—C5—C6 | 120.41 (15) | C5—C6—H6 | 119.9 |
C1—C6—C5 | 120.25 (13) | C7—C8—H8 | 119.7 |
N1—C7—C8 | 119.66 (11) | C9—C8—H8 | 119.8 |
N1—C7—C12 | 121.70 (10) | C8—C9—H9 | 119.7 |
C8—C7—C12 | 118.63 (12) | C10—C9—H9 | 119.7 |
C7—C8—C9 | 120.50 (12) | C9—C10—H10 | 120.4 |
C8—C9—C10 | 120.63 (12) | C11—C10—H10 | 120.4 |
C9—C10—C11 | 119.15 (14) | C10—C11—H11 | 119.7 |
C10—C11—C12 | 120.69 (12) | C12—C11—H11 | 119.7 |
C7—C12—C11 | 120.36 (11) | C7—C12—H12 | 119.8 |
N1—C13—C14 | 119.85 (10) | C11—C12—H12 | 119.8 |
N1—C13—C18 | 122.21 (11) | C13—C14—H14 | 119.5 |
C14—C13—C18 | 117.93 (11) | C15—C14—H14 | 119.5 |
C13—C14—C15 | 121.07 (10) | C14—C15—H15 | 119.0 |
C14—C15—C16 | 121.92 (11) | C16—C15—H15 | 119.0 |
C15—C16—C16i | 121.67 (11) | C16—C17—H17 | 118.8 |
C15—C16—C17 | 116.22 (10) | C18—C17—H17 | 118.8 |
C16i—C16—C17 | 122.11 (10) | C13—C18—H18 | 119.8 |
C16—C17—C18 | 122.40 (10) | C17—C18—H18 | 119.8 |
C13—C18—C17 | 120.43 (11) | ||
C(1)—N(1)—C(7)—C(8) | −29.27 (18) | N(1)—C(7)—C(8)—C(9) | 176.51 (12) |
C(1)—N(1)—C(7)—C(12) | 149.31 (12) | N(1)—C(7)—C(12)—C(11) | −177.89 (12) |
C(7)—N(1)—C(1)—C(2) | −47.50 (17) | C(8)—C(7)—C(12)—C(11) | 0.71 (19) |
C(7)—N(1)—C(1)—C(6) | 132.65 (13) | C(12)—C(7)—C(8)—C(9) | −2.12 (19) |
C(1)—N(1)—C(13)—C(14) | −35.87 (18) | C(7)—C(8)—C(9)—C(10) | 1.9 (2) |
C(1)—N(1)—C(13)—C(18) | 142.58 (13) | C(8)—C(9)—C(10)—C(11) | −0.1 (2) |
C(13)—N(1)—C(1)—C(2) | 131.78 (13) | C(9)—C(10)—C(11)—C(12) | −1.3 (2) |
C(13)—N(1)—C(1)—C(6) | −48.07 (17) | C(10)—C(11)—C(12)—C(7) | 1.0 (2) |
C(7)—N(1)—C(13)—C(14) | 143.40 (13) | N(1)—C(13)—C(14)—C(15) | 177.10 (12) |
C(7)—N(1)—C(13)—C(18) | −38.16 (19) | N(1)—C(13)—C(18)—C(17) | −177.79 (12) |
C(13)—N(1)—C(7)—C(8) | 151.47 (12) | C(14)—C(13)—C(18)—C(17) | 0.7 (2) |
C(13)—N(1)—C(7)—C(12) | −29.94 (18) | C(18)—C(13)—C(14)—C(15) | −1.4 (2) |
N(1)—C(1)—C(2)—C(3) | 177.90 (12) | C(13)—C(14)—C(15)—C(16) | 0.4 (2) |
N(1)—C(1)—C(6)—C(5) | −179.93 (12) | C(14)—C(15)—C(16)—C(17) | 1.39 (19) |
C(2)—C(1)—C(6)—C(5) | 0.21 (19) | C(14)—C(15)—C(16)—C(16)i | −178.00 (12) |
C(6)—C(1)—C(2)—C(3) | −2.2 (2) | C(15)—C(16)—C(16)i—C(17)i | −0.65 (19) |
C(1)—C(2)—C(3)—C(4) | 2.4 (2) | C(15)—C(16)—C(17)—C(18) | −2.1 (2) |
C(2)—C(3)—C(4)—C(5) | −0.5 (2) | C(16)i—C(16)—C(17)—C(18) | 177.25 (12) |
C(3)—C(4)—C(5)—C(6) | −1.5 (2) | C(17)—C(16)—C(16)i—C(15)i | 0.65 (19) |
C(4)—C(5)—C(6)—C(1) | 1.7 (2) | C(16)—C(17)—C(18)—C(13) | 1.1 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) −x+2, −y+1, −z+2; (vi) −x+2, −y+1, −z+1; (vii) x+1, y, z; (viii) x+1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z−1/2; (x) −x+3/2, y−1/2, −z+3/2; (xi) x−1/2, −y+1/2, z+1/2; (xii) x−1, y, z; (xiii) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C36H28N2 |
Mr | 488.63 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.6846 (2), 14.2661 (4), 9.7946 (2) |
β (°) | 107.0521 (15) |
V (Å3) | 1293.75 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.15 × 0.14 × 0.11 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.885, 0.941 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 14609, 2362, 1956 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.119, 1.07 |
No. of reflections | 2362 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.15 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).
Acknowledgements
This work was supported by a Grant-in-Aid for Scientific Research (grant No. 19350073) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
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Triarylamine-based organic semiconductors have been intensively investigated as hole transport materials for electro-optic devices (Kennedy et al., 2002; Shirota, 2000; Shirota, 2005). Recently, the organic field-effect transistor (OFET) based on a cyclic triphenylamine has been reported, which shows the relatively good mobility and high on/off ratio (Song et al., 2006). The title compound, N,N,N',N'-tetraphenyl-1,1'-biphenyl-4,4'-diamine (I), has been synthesized by coupling of two triphenylamine molecules using a copper catalyst (Ullman coupling) and also using methanesulfonic acid as catalyst in the yield of 10% (Zhang et al., 2006). We have synthesized compound (I) from the coupling of 4,4'-dibromobiphenyl and diphenylamine using a palladium catalyst in the yield of 71% (Hartwig, 1999). The crystal structure of compound (I) has been reported (Zhang et al., 2006), where the biphenyl part of the molecule is highly twisted with a dihedral angle of 32.9 (4)°. Herein, we report another crystal phase of compound (I).
The molecule (I) possesses a inversion center, thus the biphenyl moiety of the molecule shows a completely flat conformation with an average deviation of 0.0079Å (Fig. 1). The other fused rings make 69.39 (5)° and 59.53 (5)° dihedral angles with this flat biphenyl moiety. The N atom displays an almost trigonal geometry with slight distortion of the N—C bond lengths and C—N—C bond angles. The angle sums around the N atom is ca 360°. The molecular geometry of (I) is quite different from the previously reported one (Zhang et al., 2006), and also different from those of the related biphenyl-diamine compounds (Kennedy et al., 2002, Low et al., 2004; Zhang et al., 2004). The molecular packing pattern in the present crystal is also different from the reported one (Zhang et al., 2006), and a herringbone-like packing motif governed by the van der Waals interactions is observed (Fig. 2).