4-{Phen-yl[4-(6-phenyl-2,2'-bipyridin-4-yl)phen-yl]amino}-benzaldehyde.

The title mol-ecule, C35H25N3O, is a tri-phenyl-amine derivative with the 4-position substituted by an aldehyde group, and the 4'-position substituted by a 6-phenyl-2,2'-bi-pyridine group. The whole mol-ecule is non-planar and the dihedral angle between the core benzene and pyridine rings is 36.96 (5)°. The dihedral angle between the phenyl and benzaldehyde groups bonded to the amine N atom is 70.86 (5)°.

Related literature

For the application of the title compound and related mol­ecules in OLED devices, see: Neve et al. (2002 ▶); Lu et al. (2004 ▶); Ye et al. (2010 ▶). For a related mol­ecule and its application in synthesis, see: Shen et al. (2012 ▶).

Experimental

Crystal data

C35H25N3O

M = 503.58

Monoclinic,

a = 14.4204 (9) Å

b = 10.0329 (6) Å

c = 18.4597 (11) Å

β = 101.423 (1)°

V = 2617.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

13094 measured reflections

4580 independent reflections

3379 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 0.99

4580 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814013361/bh2499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013361/bh2499Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013361/bh2499Isup3.cml

CCDC reference: 965698

Additional supporting information: crystallographic information; 3D view; checkCIF report

C35H25N3O	F(000) = 1056
Mr = 503.58	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3436 reflections
a = 14.4204 (9) Å	θ = 2.3–27.3°
b = 10.0329 (6) Å	µ = 0.08 mm−1
c = 18.4597 (11) Å	T = 296 K
β = 101.423 (1)°	Needle, yellow
V = 2617.8 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	3379 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
φ and ω scans	h = −16→17
13094 measured reflections	k = −11→11
4580 independent reflections	l = −19→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.5245P] where P = (Fo2 + 2Fc2)/3
4580 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.37069 (18)	0.99664 (19)	0.85338 (11)	0.0791 (6)
H1	0.4274	1.0401	0.8523	0.095*
C2	0.37390 (13)	0.88662 (15)	0.90600 (9)	0.0578 (4)
C3	0.45768 (13)	0.85771 (16)	0.95466 (10)	0.0594 (4)
H3	0.5119	0.9061	0.9519	0.071*
C4	0.46236 (11)	0.75857 (15)	1.00714 (9)	0.0535 (4)
H4	0.5189	0.7428	1.0402	0.064*
C5	0.38289 (11)	0.68211 (14)	1.01074 (8)	0.0464 (4)
C6	0.29420 (12)	0.81128 (16)	0.91074 (9)	0.0574 (4)
H6	0.2372	0.8295	0.8788	0.069*
C7	0.29833 (11)	0.71064 (16)	0.96165 (9)	0.0525 (4)
H7	0.2444	0.6610	0.9635	0.063*
C8	0.45874 (11)	0.58033 (15)	1.12868 (8)	0.0480 (4)
C9	0.46558 (13)	0.68847 (18)	1.17592 (10)	0.0677 (5)
H9	0.4232	0.7590	1.1654	0.081*
C10	0.53571 (16)	0.6910 (2)	1.23866 (11)	0.0862 (6)
H10	0.5412	0.7646	1.2699	0.103*
C11	0.59739 (15)	0.5868 (2)	1.25570 (11)	0.0813 (6)
H11	0.6440	0.5892	1.2984	0.098*
C12	0.59008 (12)	0.4788 (2)	1.20945 (10)	0.0659 (5)
H12	0.6318	0.4077	1.2208	0.079*
C13	0.52092 (11)	0.47552 (16)	1.14605 (9)	0.0532 (4)
H13	0.5162	0.4020	1.1148	0.064*
C14	0.33521 (10)	0.45819 (14)	1.04475 (8)	0.0444 (4)
C15	0.32065 (10)	0.40549 (14)	0.97396 (8)	0.0455 (4)
H15	0.3448	0.4494	0.9373	0.055*
C16	0.30076 (11)	0.38972 (15)	1.09888 (8)	0.0498 (4)
H16	0.3111	0.4228	1.1469	0.060*
C17	0.25108 (11)	0.27239 (15)	1.08197 (8)	0.0496 (4)
H17	0.2285	0.2275	1.1190	0.059*
C18	0.27064 (10)	0.28839 (14)	0.95742 (8)	0.0448 (4)
H18	0.2612	0.2548	0.9096	0.054*
C19	0.23406 (10)	0.21983 (14)	1.01084 (8)	0.0428 (3)
C20	0.17668 (10)	0.09761 (14)	0.99163 (8)	0.0440 (4)
C21	0.11550 (10)	0.08717 (15)	0.92369 (8)	0.0463 (4)
H21	0.1127	0.1554	0.8892	0.056*
C22	0.17932 (11)	−0.00827 (15)	1.04009 (9)	0.0482 (4)
H22	0.2190	−0.0054	1.0864	0.058*
C23	0.12231 (10)	−0.11869 (15)	1.01913 (9)	0.0471 (4)
C24	0.05842 (10)	−0.02439 (15)	0.90672 (8)	0.0458 (4)
C25	−0.01267 (10)	−0.03392 (16)	0.83667 (9)	0.0491 (4)
C26	−0.03301 (12)	0.07457 (17)	0.79072 (9)	0.0605 (5)
H26	0.0004	0.1535	0.8024	0.073*
C27	−0.10196 (14)	0.0679 (2)	0.72791 (10)	0.0768 (6)
H27	−0.1148	0.1421	0.6974	0.092*
C28	−0.15196 (14)	−0.0471 (2)	0.70983 (11)	0.0812 (6)
H28	−0.1993	−0.0507	0.6676	0.097*
C29	−0.13200 (14)	−0.1569 (2)	0.75411 (11)	0.0803 (6)
H29	−0.1651	−0.2358	0.7416	0.096*
C30	−0.06295 (12)	−0.15054 (19)	0.81716 (10)	0.0655 (5)
H30	−0.0498	−0.2255	0.8471	0.079*
C31	0.12354 (12)	−0.23332 (15)	1.07047 (9)	0.0525 (4)
C32	0.05216 (13)	−0.32814 (17)	1.05889 (11)	0.0671 (5)
H32	0.0041	−0.3243	1.0171	0.081*
C33	0.05354 (17)	−0.42849 (19)	1.11039 (14)	0.0840 (6)
H33	0.0061	−0.4927	1.1040	0.101*
C34	0.12583 (18)	−0.4321 (2)	1.17110 (13)	0.0866 (7)
H34	0.1278	−0.4980	1.2068	0.104*
C35	0.19494 (16)	−0.3370 (2)	1.17810 (11)	0.0779 (6)
H35	0.2443	−0.3413	1.2190	0.093*
N1	0.38793 (9)	0.57802 (12)	1.06252 (7)	0.0509 (3)
N2	0.06237 (9)	−0.12729 (12)	0.95393 (7)	0.0495 (3)
N3	0.19577 (11)	−0.23785 (14)	1.12957 (8)	0.0671 (4)
O1	0.30133 (13)	1.03588 (14)	0.81138 (8)	0.1031 (5)

	U11	U22	U33	U12	U13	U23
C1	0.1167 (18)	0.0504 (12)	0.0663 (13)	−0.0151 (11)	0.0088 (12)	−0.0004 (9)
C2	0.0786 (12)	0.0372 (9)	0.0575 (10)	−0.0051 (8)	0.0130 (9)	−0.0056 (8)
C3	0.0693 (11)	0.0409 (9)	0.0693 (11)	−0.0146 (8)	0.0165 (9)	−0.0076 (8)
C4	0.0525 (9)	0.0423 (9)	0.0634 (10)	−0.0052 (7)	0.0057 (8)	−0.0071 (8)
C5	0.0516 (9)	0.0341 (8)	0.0534 (9)	−0.0024 (7)	0.0100 (7)	−0.0070 (7)
C6	0.0640 (11)	0.0464 (10)	0.0584 (10)	0.0044 (8)	0.0040 (8)	−0.0031 (8)
C7	0.0514 (9)	0.0439 (9)	0.0613 (10)	−0.0018 (7)	0.0090 (8)	−0.0019 (8)
C8	0.0517 (9)	0.0446 (9)	0.0463 (9)	−0.0109 (7)	0.0064 (7)	−0.0059 (7)
C9	0.0750 (12)	0.0563 (11)	0.0679 (12)	−0.0007 (9)	0.0044 (10)	−0.0186 (9)
C10	0.0982 (16)	0.0834 (15)	0.0690 (13)	−0.0116 (13)	−0.0029 (12)	−0.0342 (11)
C11	0.0761 (14)	0.0958 (16)	0.0616 (12)	−0.0156 (12)	−0.0117 (10)	−0.0108 (12)
C12	0.0583 (11)	0.0707 (12)	0.0644 (11)	−0.0019 (9)	0.0018 (9)	0.0059 (10)
C13	0.0587 (10)	0.0493 (9)	0.0509 (9)	−0.0054 (8)	0.0094 (8)	−0.0040 (7)
C14	0.0439 (8)	0.0382 (8)	0.0483 (9)	−0.0039 (6)	0.0027 (7)	−0.0028 (7)
C15	0.0477 (9)	0.0428 (9)	0.0448 (9)	−0.0048 (7)	0.0067 (7)	0.0019 (7)
C16	0.0557 (10)	0.0498 (9)	0.0427 (9)	−0.0058 (8)	0.0065 (7)	−0.0052 (7)
C17	0.0529 (9)	0.0497 (9)	0.0456 (9)	−0.0076 (7)	0.0087 (7)	0.0014 (7)
C18	0.0485 (9)	0.0431 (9)	0.0399 (8)	−0.0037 (7)	0.0016 (7)	−0.0024 (7)
C19	0.0402 (8)	0.0389 (8)	0.0461 (8)	−0.0013 (6)	0.0011 (6)	0.0017 (7)
C20	0.0406 (8)	0.0402 (8)	0.0503 (9)	−0.0017 (6)	0.0070 (7)	−0.0021 (7)
C21	0.0452 (9)	0.0412 (8)	0.0507 (9)	−0.0041 (7)	0.0052 (7)	0.0012 (7)
C22	0.0485 (9)	0.0434 (9)	0.0504 (9)	−0.0012 (7)	0.0043 (7)	0.0009 (7)
C23	0.0468 (9)	0.0398 (9)	0.0563 (10)	0.0013 (7)	0.0141 (8)	−0.0008 (7)
C24	0.0395 (8)	0.0447 (9)	0.0530 (9)	−0.0002 (7)	0.0088 (7)	−0.0062 (7)
C25	0.0396 (8)	0.0544 (10)	0.0531 (9)	−0.0021 (7)	0.0087 (7)	−0.0129 (8)
C26	0.0576 (10)	0.0561 (11)	0.0597 (11)	−0.0005 (8)	−0.0078 (8)	−0.0100 (9)
C27	0.0779 (13)	0.0788 (14)	0.0638 (12)	0.0131 (11)	−0.0100 (10)	−0.0118 (10)
C28	0.0628 (12)	0.1089 (18)	0.0632 (13)	−0.0024 (12)	−0.0087 (10)	−0.0298 (13)
C29	0.0735 (13)	0.0929 (16)	0.0706 (13)	−0.0309 (12)	0.0050 (11)	−0.0278 (12)
C30	0.0649 (11)	0.0687 (12)	0.0622 (11)	−0.0189 (9)	0.0105 (9)	−0.0156 (9)
C31	0.0577 (10)	0.0404 (9)	0.0624 (10)	0.0032 (7)	0.0196 (9)	0.0016 (8)
C32	0.0744 (12)	0.0468 (10)	0.0840 (13)	−0.0080 (9)	0.0253 (10)	0.0021 (9)
C33	0.0977 (16)	0.0487 (12)	0.1151 (18)	−0.0098 (11)	0.0440 (15)	0.0100 (12)
C34	0.1124 (18)	0.0597 (13)	0.0973 (17)	0.0124 (13)	0.0443 (15)	0.0286 (12)
C35	0.0916 (15)	0.0655 (13)	0.0790 (14)	0.0144 (11)	0.0229 (11)	0.0226 (11)
N1	0.0563 (8)	0.0399 (7)	0.0519 (8)	−0.0098 (6)	−0.0004 (6)	−0.0030 (6)
N2	0.0468 (7)	0.0425 (7)	0.0593 (8)	−0.0037 (6)	0.0106 (6)	−0.0037 (6)
N3	0.0734 (10)	0.0582 (9)	0.0706 (10)	0.0078 (7)	0.0166 (8)	0.0156 (8)
O1	0.1452 (15)	0.0692 (10)	0.0818 (10)	−0.0054 (9)	−0.0088 (10)	0.0165 (8)

C1—O1	1.204 (2)	C18—C19	1.389 (2)
C1—C2	1.465 (2)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.4826 (19)
C2—C3	1.386 (2)	C20—C22	1.384 (2)
C2—C6	1.393 (2)	C20—C21	1.3870 (19)
C3—C4	1.381 (2)	C21—C24	1.388 (2)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.391 (2)	C22—C23	1.388 (2)
C4—H4	0.9300	C22—H22	0.9300
C5—C7	1.397 (2)	C23—N2	1.3384 (19)
C5—N1	1.4079 (19)	C23—C31	1.488 (2)
C6—C7	1.373 (2)	C24—N2	1.3449 (19)
C6—H6	0.9300	C24—C25	1.486 (2)
C7—H7	0.9300	C25—C26	1.375 (2)
C8—C13	1.378 (2)	C25—C30	1.386 (2)
C8—C9	1.383 (2)	C26—C27	1.371 (2)
C8—N1	1.4285 (18)	C26—H26	0.9300
C9—C10	1.379 (3)	C27—C28	1.367 (3)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.368 (3)	C28—C29	1.368 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.370 (3)	C29—C30	1.375 (2)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.379 (2)	C30—H30	0.9300
C12—H12	0.9300	C31—N3	1.352 (2)
C13—H13	0.9300	C31—C32	1.387 (2)
C14—C15	1.387 (2)	C32—C33	1.382 (3)
C14—C16	1.383 (2)	C32—H32	0.9300
C14—N1	1.4256 (18)	C33—C34	1.371 (3)
C15—C18	1.381 (2)	C33—H33	0.9300
C15—H15	0.9300	C34—C35	1.368 (3)
C16—C17	1.381 (2)	C34—H34	0.9300
C16—H16	0.9300	C35—N3	1.340 (2)
C17—C19	1.391 (2)	C35—H35	0.9300
C17—H17	0.9300
O1—C1—C2	125.9 (2)	C18—C19—C20	120.80 (13)
O1—C1—H1	117.0	C17—C19—C20	121.68 (13)
C2—C1—H1	117.0	C22—C20—C21	117.23 (14)
C3—C2—C6	118.04 (16)	C22—C20—C19	122.51 (13)
C3—C2—C1	119.76 (17)	C21—C20—C19	120.25 (13)
C6—C2—C1	122.17 (18)	C20—C21—C24	120.50 (14)
C2—C3—C4	121.38 (16)	C20—C21—H21	119.7
C2—C3—H3	119.3	C24—C21—H21	119.7
C4—C3—H3	119.3	C20—C22—C23	119.56 (14)
C3—C4—C5	120.28 (15)	C20—C22—H22	120.2
C3—C4—H4	119.9	C23—C22—H22	120.2
C5—C4—H4	119.9	N2—C23—C22	122.92 (14)
C4—C5—C7	118.52 (15)	N2—C23—C31	116.55 (14)
C4—C5—N1	120.60 (14)	C22—C23—C31	120.50 (14)
C7—C5—N1	120.88 (14)	N2—C24—C21	121.71 (14)
C7—C6—C2	121.19 (16)	N2—C24—C25	116.61 (13)
C7—C6—H6	119.4	C21—C24—C25	121.64 (14)
C2—C6—H6	119.4	C26—C25—C30	118.11 (16)
C6—C7—C5	120.57 (15)	C26—C25—C24	120.79 (14)
C6—C7—H7	119.7	C30—C25—C24	121.05 (16)
C5—C7—H7	119.7	C25—C26—C27	120.87 (17)
C13—C8—C9	119.34 (15)	C25—C26—H26	119.6
C13—C8—N1	120.57 (14)	C27—C26—H26	119.6
C9—C8—N1	120.09 (15)	C26—C27—C28	120.4 (2)
C10—C9—C8	119.52 (18)	C26—C27—H27	119.8
C10—C9—H9	120.2	C28—C27—H27	119.8
C8—C9—H9	120.2	C29—C28—C27	119.71 (18)
C11—C10—C9	120.97 (18)	C29—C28—H28	120.1
C11—C10—H10	119.5	C27—C28—H28	120.1
C9—C10—H10	119.5	C28—C29—C30	119.99 (19)
C10—C11—C12	119.63 (18)	C28—C29—H29	120.0
C10—C11—H11	120.2	C30—C29—H29	120.0
C12—C11—H11	120.2	C29—C30—C25	120.86 (19)
C11—C12—C13	120.07 (18)	C29—C30—H30	119.6
C11—C12—H12	120.0	C25—C30—H30	119.6
C13—C12—H12	120.0	N3—C31—C32	122.08 (16)
C8—C13—C12	120.46 (16)	N3—C31—C23	116.75 (14)
C8—C13—H13	119.8	C32—C31—C23	121.14 (16)
C12—C13—H13	119.8	C33—C32—C31	118.99 (19)
C15—C14—C16	118.84 (13)	C33—C32—H32	120.5
C15—C14—N1	120.85 (13)	C31—C32—H32	120.5
C16—C14—N1	120.26 (13)	C34—C33—C32	119.1 (2)
C14—C15—C18	120.52 (14)	C34—C33—H33	120.4
C14—C15—H15	119.7	C32—C33—H33	120.4
C18—C15—H15	119.7	C35—C34—C33	118.71 (19)
C17—C16—C14	120.29 (14)	C35—C34—H34	120.6
C17—C16—H16	119.9	C33—C34—H34	120.6
C14—C16—H16	119.9	N3—C35—C34	123.9 (2)
C16—C17—C19	121.53 (14)	N3—C35—H35	118.1
C16—C17—H17	119.2	C34—C35—H35	118.1
C19—C17—H17	119.2	C5—N1—C14	121.05 (12)
C15—C18—C19	121.30 (14)	C5—N1—C8	120.03 (12)
C15—C18—H18	119.4	C14—N1—C8	117.96 (12)
C19—C18—H18	119.4	C23—N2—C24	118.04 (13)
C18—C19—C17	117.49 (13)	C35—N3—C31	117.20 (17)