A new crystal phase of N,N,N',N'-tetra-phenyl-1,1'-biphenyl-4,4'-diamine.

The complete molecule of the title compound, C(36)H(28)N(2), 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

C36H28N2

M = 488.63

Monoclinic,

a = 9.6846 (2) Å

b = 14.2661 (4) Å

c = 9.7946 (2) Å

β = 107.0521 (15)°

V = 1293.75 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.56 mm−1

T = 173 K

0.15 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.885, T max = 0.941

14609 measured reflections

2362 independent reflections

1956 reflections with F 2 > 2σ(F 2)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.119

S = 1.07

2362 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.15 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016389/bq2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016389/bq2132Isup2.hkl

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

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)

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)