6-[4-(Diphenyl-amino)-phen-yl]quinoline 1-oxide.

In the title mol-ecule, C(27)H(20)N(2)O, a triphenyl-amine derivative of quinoline, the three benzene rings linked through an N atom form a propeller shape, with dihedral angles between the mean planes of pairs of rings of 75.57 (9), 55.68 (9) and 83.66 (9)°. The quinoline ring is essentially planar, with an r.m.s. deviation of the fitted atoms of 0.0155 Å, and forms a dihedral angle of 33.52 (8)° with the benzene ring to which it is bonded. Weak C-H⋯π inter-actions are also observed in the crystal structure.

Related literature

For background to triphenyl­amine derivatives, see: Lin et al. (2010 ▶). For preparation, see: Liu et al. (2011 ▶). For the crystal structure of a related compound, see: Xie et al. (2011 ▶).

Experimental

Crystal data

C27H20N2O

M = 388.45

Monoclinic,

a = 16.774 (3) Å

b = 9.6130 (19) Å

c = 13.253 (3) Å

β = 107.05 (3)°

V = 2043.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.977, T max = 0.992

3881 measured reflections

3747 independent reflections

2263 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.156

S = 1.00

3747 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031662/pv2553sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031662/pv2553Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031662/pv2553Isup3.cml

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

C27H20N2O	F(000) = 816
Mr = 388.45	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.774 (3) Å	θ = 9–13°
b = 9.6130 (19) Å	µ = 0.08 mm−1
c = 13.253 (3) Å	T = 293 K
β = 107.05 (3)°	Block, colourless
V = 2043.1 (7) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2263 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
Graphite monochromator	θmax = 25.4°, θmin = 1.3°
ω/2θ scans	h = −20→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.977, Tmax = 0.992	l = −15→15
3881 measured reflections	3 standard reflections every 200 reflections
3747 independent reflections	intensity decay: 1%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3
3747 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O	0.46148 (12)	−0.0633 (2)	−0.26382 (13)	0.0624 (5)
N1	0.17381 (14)	0.1024 (2)	0.34131 (16)	0.0563 (6)
C1	0.22097 (18)	0.0401 (3)	0.5285 (2)	0.0637 (8)
H1A	0.2412	0.1298	0.5452	0.076*
N2	0.47292 (13)	−0.1387 (2)	−0.17945 (15)	0.0471 (5)
C2	0.2295 (2)	−0.0578 (4)	0.6077 (2)	0.0727 (9)
H2A	0.2556	−0.0333	0.6775	0.087*
C3	0.1999 (2)	−0.1898 (3)	0.5843 (3)	0.0747 (9)
H3A	0.2055	−0.2551	0.6378	0.090*
C4	0.1622 (2)	−0.2248 (3)	0.4821 (3)	0.0796 (9)
H4A	0.1420	−0.3146	0.4657	0.096*
C5	0.1536 (2)	−0.1290 (3)	0.4029 (2)	0.0670 (8)
H5A	0.1279	−0.1549	0.3333	0.080*
C6	0.18249 (16)	0.0043 (3)	0.42509 (19)	0.0497 (7)
C7	0.12495 (15)	0.2234 (3)	0.33659 (18)	0.0471 (6)
C8	0.13847 (16)	0.3420 (3)	0.2849 (2)	0.0538 (7)
H8A	0.1800	0.3422	0.2514	0.065*
C9	0.09116 (19)	0.4601 (3)	0.2823 (2)	0.0653 (8)
H9A	0.1002	0.5384	0.2459	0.078*
C10	0.0310 (2)	0.4622 (3)	0.3332 (2)	0.0721 (9)
H10A	−0.0001	0.5426	0.3325	0.086*
C11	0.01655 (17)	0.3467 (3)	0.3850 (2)	0.0667 (8)
H11A	−0.0246	0.3487	0.4191	0.080*
C12	0.06248 (16)	0.2266 (3)	0.3871 (2)	0.0572 (7)
H12A	0.0519	0.1481	0.4221	0.069*
C13	0.21718 (15)	0.0743 (3)	0.26611 (19)	0.0475 (6)
C14	0.29592 (17)	0.0150 (3)	0.29892 (19)	0.0558 (7)
H14A	0.3203	−0.0034	0.3702	0.067*
C15	0.33867 (16)	−0.0169 (3)	0.22768 (19)	0.0539 (7)
H15A	0.3917	−0.0554	0.2519	0.065*
C16	0.30402 (15)	0.0074 (3)	0.12001 (18)	0.0429 (6)
C17	0.22541 (15)	0.0677 (2)	0.08783 (19)	0.0452 (6)
H17A	0.2012	0.0869	0.0166	0.054*
C18	0.18226 (15)	0.0998 (3)	0.15911 (19)	0.0485 (6)
H18A	0.1293	0.1389	0.1351	0.058*
C19	0.34862 (14)	−0.0321 (2)	0.04275 (18)	0.0426 (6)
C20	0.39816 (15)	−0.1491 (2)	0.05721 (18)	0.0454 (6)
H20A	0.4031	−0.2046	0.1162	0.054*
C21	0.44174 (14)	−0.1874 (2)	−0.01543 (18)	0.0420 (6)
C22	0.43129 (14)	−0.1041 (2)	−0.10499 (17)	0.0411 (6)
C23	0.38061 (15)	0.0147 (3)	−0.12111 (18)	0.0463 (6)
H23A	0.3742	0.0696	−0.1807	0.056*
C24	0.34094 (15)	0.0486 (3)	−0.04859 (18)	0.0464 (6)
H24A	0.3076	0.1277	−0.0595	0.056*
C25	0.49522 (16)	−0.3042 (2)	0.0002 (2)	0.0498 (6)
H25A	0.5029	−0.3606	0.0593	0.060*
C26	0.53503 (16)	−0.3321 (3)	−0.0729 (2)	0.0521 (7)
H26A	0.5707	−0.4082	−0.0634	0.062*
C27	0.52346 (16)	−0.2490 (3)	−0.1614 (2)	0.0522 (7)
H27A	0.5519	−0.2708	−0.2100	0.063*

	U11	U22	U33	U12	U13	U23
O	0.0795 (13)	0.0698 (13)	0.0483 (11)	0.0007 (11)	0.0350 (10)	0.0082 (9)
N1	0.0731 (15)	0.0497 (13)	0.0605 (14)	0.0173 (11)	0.0418 (12)	0.0101 (11)
C1	0.076 (2)	0.0584 (18)	0.0597 (18)	−0.0005 (15)	0.0241 (16)	−0.0076 (14)
N2	0.0530 (13)	0.0484 (13)	0.0458 (12)	−0.0104 (11)	0.0237 (10)	−0.0059 (10)
C2	0.089 (2)	0.080 (2)	0.0463 (16)	0.0161 (19)	0.0160 (16)	0.0009 (16)
C3	0.094 (2)	0.068 (2)	0.070 (2)	0.0229 (19)	0.0360 (19)	0.0199 (17)
C4	0.109 (3)	0.0521 (18)	0.076 (2)	−0.0056 (18)	0.024 (2)	0.0076 (16)
C5	0.088 (2)	0.0549 (19)	0.0540 (17)	−0.0036 (16)	0.0154 (16)	−0.0014 (14)
C6	0.0578 (16)	0.0510 (16)	0.0478 (15)	0.0084 (13)	0.0272 (13)	0.0023 (13)
C7	0.0494 (15)	0.0502 (15)	0.0437 (14)	0.0035 (13)	0.0169 (12)	−0.0062 (12)
C8	0.0576 (17)	0.0519 (16)	0.0567 (16)	0.0043 (13)	0.0243 (13)	−0.0005 (13)
C9	0.075 (2)	0.0537 (18)	0.0669 (19)	0.0112 (16)	0.0198 (16)	0.0018 (14)
C10	0.068 (2)	0.070 (2)	0.077 (2)	0.0271 (17)	0.0189 (17)	−0.0024 (17)
C11	0.0471 (16)	0.086 (2)	0.073 (2)	0.0103 (16)	0.0255 (15)	−0.0120 (17)
C12	0.0529 (16)	0.0635 (18)	0.0618 (17)	−0.0021 (14)	0.0272 (14)	−0.0056 (14)
C13	0.0518 (15)	0.0479 (15)	0.0495 (15)	0.0058 (13)	0.0250 (12)	0.0010 (12)
C14	0.0594 (17)	0.0701 (18)	0.0408 (14)	0.0126 (15)	0.0190 (13)	0.0014 (13)
C15	0.0465 (15)	0.0670 (18)	0.0503 (15)	0.0106 (13)	0.0174 (12)	0.0012 (13)
C16	0.0466 (14)	0.0422 (13)	0.0429 (13)	−0.0006 (12)	0.0178 (11)	−0.0025 (11)
C17	0.0473 (14)	0.0470 (14)	0.0427 (13)	0.0035 (12)	0.0154 (11)	0.0027 (11)
C18	0.0459 (14)	0.0528 (15)	0.0522 (15)	0.0081 (12)	0.0227 (12)	0.0028 (12)
C19	0.0398 (13)	0.0449 (14)	0.0448 (14)	−0.0029 (11)	0.0151 (11)	−0.0030 (11)
C20	0.0495 (14)	0.0486 (15)	0.0407 (13)	−0.0009 (13)	0.0175 (11)	0.0047 (11)
C21	0.0432 (13)	0.0398 (14)	0.0459 (14)	−0.0055 (11)	0.0175 (11)	−0.0028 (11)
C22	0.0441 (13)	0.0425 (14)	0.0394 (13)	−0.0085 (11)	0.0168 (11)	−0.0066 (11)
C23	0.0470 (14)	0.0505 (15)	0.0427 (13)	−0.0033 (12)	0.0153 (11)	0.0069 (11)
C24	0.0446 (14)	0.0460 (15)	0.0513 (14)	0.0036 (12)	0.0181 (12)	0.0026 (12)
C25	0.0589 (16)	0.0408 (14)	0.0541 (15)	−0.0003 (13)	0.0232 (13)	−0.0004 (12)
C26	0.0572 (16)	0.0432 (15)	0.0604 (17)	0.0019 (13)	0.0246 (14)	−0.0075 (13)
C27	0.0579 (16)	0.0487 (16)	0.0585 (16)	−0.0062 (14)	0.0305 (13)	−0.0136 (13)

O—N2	1.299 (2)	C12—H12A	0.9300
N1—C7	1.414 (3)	C13—C14	1.386 (3)
N1—C13	1.421 (3)	C13—C18	1.388 (3)
N1—C6	1.431 (3)	C14—C15	1.377 (3)
C1—C6	1.377 (4)	C14—H14A	0.9300
C1—C2	1.385 (4)	C15—C16	1.394 (3)
C1—H1A	0.9300	C15—H15A	0.9300
N2—C27	1.334 (3)	C16—C17	1.388 (3)
N2—C22	1.406 (3)	C16—C19	1.484 (3)
C2—C3	1.365 (4)	C17—C18	1.383 (3)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.359 (4)	C18—H18A	0.9300
C3—H3A	0.9300	C19—C20	1.379 (3)
C4—C5	1.371 (4)	C19—C24	1.411 (3)
C4—H4A	0.9300	C20—C21	1.417 (3)
C5—C6	1.371 (4)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.399 (3)
C7—C8	1.383 (3)	C21—C25	1.414 (3)
C7—C12	1.400 (3)	C22—C23	1.402 (3)
C8—C9	1.380 (4)	C23—C24	1.359 (3)
C8—H8A	0.9300	C23—H23A	0.9300
C9—C10	1.369 (4)	C24—H24A	0.9300
C9—H9A	0.9300	C25—C26	1.355 (3)
C10—C11	1.363 (4)	C25—H25A	0.9300
C10—H10A	0.9300	C26—C27	1.386 (4)
C11—C12	1.384 (4)	C26—H26A	0.9300
C11—H11A	0.9300	C27—H27A	0.9300
C7—N1—C13	122.3 (2)	C18—C13—N1	122.2 (2)
C7—N1—C6	120.13 (19)	C15—C14—C13	121.1 (2)
C13—N1—C6	117.5 (2)	C15—C14—H14A	119.5
C6—C1—C2	119.9 (3)	C13—C14—H14A	119.5
C6—C1—H1A	120.0	C14—C15—C16	121.3 (2)
C2—C1—H1A	120.0	C14—C15—H15A	119.3
O—N2—C27	121.6 (2)	C16—C15—H15A	119.3
O—N2—C22	119.6 (2)	C17—C16—C15	117.3 (2)
C27—N2—C22	118.9 (2)	C17—C16—C19	121.4 (2)
C3—C2—C1	120.7 (3)	C15—C16—C19	121.4 (2)
C3—C2—H2A	119.7	C18—C17—C16	121.6 (2)
C1—C2—H2A	119.7	C18—C17—H17A	119.2
C4—C3—C2	119.2 (3)	C16—C17—H17A	119.2
C4—C3—H3A	120.4	C17—C18—C13	120.6 (2)
C2—C3—H3A	120.4	C17—C18—H18A	119.7
C3—C4—C5	120.7 (3)	C13—C18—H18A	119.7
C3—C4—H4A	119.6	C20—C19—C24	117.9 (2)
C5—C4—H4A	119.6	C20—C19—C16	121.2 (2)
C4—C5—C6	120.8 (3)	C24—C19—C16	120.9 (2)
C4—C5—H5A	119.6	C19—C20—C21	121.8 (2)
C6—C5—H5A	119.6	C19—C20—H20A	119.1
C5—C6—C1	118.7 (3)	C21—C20—H20A	119.1
C5—C6—N1	120.0 (2)	C22—C21—C25	119.7 (2)
C1—C6—N1	121.3 (3)	C22—C21—C20	117.8 (2)
C8—C7—C12	118.3 (2)	C25—C21—C20	122.5 (2)
C8—C7—N1	121.5 (2)	C21—C22—C23	121.0 (2)
C12—C7—N1	120.2 (2)	C21—C22—N2	119.7 (2)
C9—C8—C7	120.9 (2)	C23—C22—N2	119.3 (2)
C9—C8—H8A	119.5	C24—C23—C22	119.2 (2)
C7—C8—H8A	119.5	C24—C23—H23A	120.4
C10—C9—C8	120.1 (3)	C22—C23—H23A	120.4
C10—C9—H9A	119.9	C23—C24—C19	122.3 (2)
C8—C9—H9A	119.9	C23—C24—H24A	118.9
C11—C10—C9	120.1 (3)	C19—C24—H24A	118.9
C11—C10—H10A	120.0	C26—C25—C21	118.5 (2)
C9—C10—H10A	120.0	C26—C25—H25A	120.8
C10—C11—C12	120.7 (3)	C21—C25—H25A	120.8
C10—C11—H11A	119.7	C25—C26—C27	121.0 (2)
C12—C11—H11A	119.7	C25—C26—H26A	119.5
C11—C12—C7	119.9 (3)	C27—C26—H26A	119.5
C11—C12—H12A	120.0	N2—C27—C26	122.2 (2)
C7—C12—H12A	120.0	N2—C27—H27A	118.9
C14—C13—C18	118.1 (2)	C26—C27—H27A	118.9
C14—C13—N1	119.6 (2)
C6—C1—C2—C3	−0.1 (4)	C15—C16—C17—C18	−1.3 (4)
C1—C2—C3—C4	0.3 (5)	C19—C16—C17—C18	177.5 (2)
C2—C3—C4—C5	−0.1 (5)	C16—C17—C18—C13	0.9 (4)
C3—C4—C5—C6	−0.4 (5)	C14—C13—C18—C17	−0.4 (4)
C4—C5—C6—C1	0.5 (4)	N1—C13—C18—C17	−178.2 (2)
C4—C5—C6—N1	179.3 (3)	C17—C16—C19—C20	−144.3 (2)
C2—C1—C6—C5	−0.3 (4)	C15—C16—C19—C20	34.5 (4)
C2—C1—C6—N1	−179.1 (2)	C17—C16—C19—C24	35.0 (3)
C7—N1—C6—C5	117.4 (3)	C15—C16—C19—C24	−146.2 (2)
C13—N1—C6—C5	−63.9 (3)	C24—C19—C20—C21	1.2 (3)
C7—N1—C6—C1	−63.8 (3)	C16—C19—C20—C21	−179.4 (2)
C13—N1—C6—C1	114.9 (3)	C19—C20—C21—C22	−1.7 (3)
C13—N1—C7—C8	−23.1 (4)	C19—C20—C21—C25	177.6 (2)
C6—N1—C7—C8	155.5 (2)	C25—C21—C22—C23	−178.1 (2)
C13—N1—C7—C12	158.5 (2)	C20—C21—C22—C23	1.2 (3)
C6—N1—C7—C12	−22.9 (4)	C25—C21—C22—N2	1.1 (3)
C12—C7—C8—C9	−0.6 (4)	C20—C21—C22—N2	−179.6 (2)
N1—C7—C8—C9	−179.0 (2)	O—N2—C22—C21	178.3 (2)
C7—C8—C9—C10	1.4 (4)	C27—N2—C22—C21	−1.7 (3)
C8—C9—C10—C11	−1.2 (5)	O—N2—C22—C23	−2.5 (3)
C9—C10—C11—C12	0.3 (5)	C27—N2—C22—C23	177.5 (2)
C10—C11—C12—C7	0.5 (4)	C21—C22—C23—C24	−0.3 (4)
C8—C7—C12—C11	−0.4 (4)	N2—C22—C23—C24	−179.5 (2)
N1—C7—C12—C11	178.0 (2)	C22—C23—C24—C19	−0.3 (4)
C7—N1—C13—C14	141.4 (3)	C20—C19—C24—C23	−0.2 (3)
C6—N1—C13—C14	−37.3 (4)	C16—C19—C24—C23	−179.6 (2)
C7—N1—C13—C18	−40.8 (4)	C22—C21—C25—C26	0.0 (3)
C6—N1—C13—C18	140.5 (3)	C20—C21—C25—C26	−179.3 (2)
C18—C13—C14—C15	0.4 (4)	C21—C25—C26—C27	−0.4 (4)
N1—C13—C14—C15	178.3 (2)	O—N2—C27—C26	−178.7 (2)
C13—C14—C15—C16	−0.8 (4)	C22—N2—C27—C26	1.3 (4)
C14—C15—C16—C17	1.3 (4)	C25—C26—C27—N2	−0.2 (4)
C14—C15—C16—C19	−177.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cg3i	0.93	2.76	3.640 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg3i	0.93	2.76	3.640 (3)	158

Symmetry code: (i) .