4-(4-Nitro-styr-yl)-N,N-diphenyl-aniline.

In the triaryl-amine group of the title compound, C(26)H(20)N(2)O(2), the N atom adopts an approximately trigonal-planar geometry, lying 0.046 (5) Å from the plane P defined by its three neighbouring C atoms; the benzene and two terminal phenyl rings are twisted by 37.4 (1), 31.4 (1) and 47.8 (1)°, respectively from plane P. In the trans-stilbene fragment, the two benzene rings form a dihedral angle of 31.3 (1)°. In the crystal, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into ribbons in [100].

Related literature

For a related structure, see: Yang et al. (2003 ▶). For background to push–pull chromophores, see: Marder et al. (1991 ▶); Reinhardt et al. (1998 ▶).

Experimental

Crystal data

C26H20N2O2

M = 392.44

Monoclinic,

a = 8.4884 (3) Å

b = 8.9834 (3) Å

c = 27.0880 (8) Å

β = 96.500 (2)°

V = 2052.31 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.984

7675 measured reflections

3606 independent reflections

2213 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.185

S = 1.04

3606 reflections

272 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.20 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/S1600536812023719/cv5302sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023719/cv5302Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023719/cv5302Isup3.cml

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

C26H20N2O2	F(000) = 824
Mr = 392.44	Dx = 1.270 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1419 reflections
a = 8.4884 (3) Å	θ = 2.4–21.1°
b = 8.9834 (3) Å	µ = 0.08 mm−1
c = 27.0880 (8) Å	T = 298 K
β = 96.500 (2)°	Red, block
V = 2052.31 (12) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2213 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
phi and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.976, Tmax = 0.984	k = −10→7
7675 measured reflections	l = −32→32

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.185	w = 1/[σ2(Fo2) + (0.0857P)2 + 0.4264P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3606 reflections	Δρmax = 0.44 e Å−3
272 parameters	Δρmin = −0.20 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (17)

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.

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 > σ(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
O1	0.1022 (4)	0.1217 (4)	1.06736 (14)	0.1466 (14)
O2	0.2236 (5)	−0.0213 (4)	1.02338 (11)	0.1424 (13)
N1	0.4781 (2)	1.2271 (2)	0.81947 (8)	0.0608 (6)
N2	0.1826 (4)	0.1004 (4)	1.03580 (13)	0.0983 (10)
C1	0.3616 (3)	1.3187 (3)	0.78910 (9)	0.0553 (7)
C2	0.3483 (3)	1.4677 (3)	0.79922 (10)	0.0654 (7)
H2	0.4128	1.5106	0.8254	0.078*
C3	0.2364 (4)	1.5551 (4)	0.76972 (13)	0.0805 (9)
H3	0.2289	1.6559	0.7770	0.097*
C4	0.1355 (4)	1.4960 (5)	0.72958 (14)	0.0883 (10)
H4	0.0631	1.5566	0.7107	0.106*
C5	0.1463 (4)	1.3478 (4)	0.71906 (13)	0.0938 (11)
H5	0.0806	1.3053	0.6930	0.113*
C6	0.2598 (4)	1.2596 (3)	0.74862 (11)	0.0808 (9)
H6	0.2677	1.1590	0.7411	0.097*
C7	0.6385 (3)	1.2784 (3)	0.83323 (9)	0.0520 (6)
C8	0.7061 (3)	1.3620 (3)	0.80040 (11)	0.0685 (8)
H8	0.6519	1.3862	0.7697	0.082*
C9	0.8628 (4)	1.4119 (3)	0.81420 (15)	0.0855 (10)
H9	0.9097	1.4701	0.7915	0.103*
C10	0.9527 (4)	1.3801 (3)	0.85959 (15)	0.0848 (10)
H10	1.0551	1.4169	0.8667	0.102*
C11	0.8878 (4)	1.2964 (3)	0.89204 (12)	0.0769 (8)
H11	0.9441	1.2712	0.9224	0.092*
C12	0.7319 (3)	1.2467 (3)	0.87945 (10)	0.0638 (7)
H12	0.6861	1.1894	0.9026	0.077*
C13	0.4293 (3)	1.0942 (3)	0.83959 (9)	0.0550 (7)
C14	0.2812 (3)	1.0854 (3)	0.85408 (10)	0.0634 (7)
H14	0.2101	1.1638	0.8479	0.076*
C15	0.2386 (4)	0.9612 (3)	0.87764 (11)	0.0701 (8)
H15	0.1375	0.9567	0.8877	0.084*
C16	0.3393 (3)	0.8402 (3)	0.88742 (10)	0.0664 (7)
C17	0.4834 (3)	0.8447 (3)	0.87023 (11)	0.0679 (7)
H17	0.5512	0.7634	0.8746	0.081*
C18	0.5286 (3)	0.9702 (3)	0.84636 (11)	0.0667 (7)
H18	0.6272	0.9725	0.8345	0.080*
C19	0.2936 (4)	0.7155 (3)	0.91720 (11)	0.0761 (8)
H19	0.1950	0.7239	0.9288	0.091*
C20	0.3702 (4)	0.5964 (3)	0.92954 (11)	0.0729 (8)
H20	0.4687	0.5873	0.9180	0.088*
C21	0.3225 (3)	0.4725 (3)	0.95959 (10)	0.0640 (7)
C22	0.2273 (3)	0.4916 (3)	0.99516 (12)	0.0730 (8)
H22	0.1908	0.5861	1.0021	0.088*
C23	0.1839 (3)	0.3702 (4)	1.02138 (12)	0.0793 (9)
H23	0.1189	0.3830	1.0465	0.095*
C24	0.2349 (3)	0.2320 (3)	1.01095 (11)	0.0691 (8)
C25	0.3328 (4)	0.2112 (3)	0.97748 (11)	0.0768 (9)
H25	0.3709	0.1169	0.9711	0.092*
C26	0.3760 (4)	0.3325 (3)	0.95259 (11)	0.0752 (8)
H26	0.4469	0.3190	0.9292	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.102 (2)	0.178 (3)	0.165 (3)	−0.0168 (19)	0.041 (2)	0.086 (2)
O2	0.225 (4)	0.0826 (19)	0.114 (2)	−0.039 (2)	−0.005 (2)	0.0338 (17)
N1	0.0531 (13)	0.0507 (13)	0.0774 (15)	−0.0088 (10)	0.0022 (11)	0.0142 (11)
N2	0.093 (2)	0.103 (3)	0.093 (2)	−0.029 (2)	−0.0151 (18)	0.038 (2)
C1	0.0514 (15)	0.0541 (16)	0.0602 (15)	−0.0067 (12)	0.0048 (12)	0.0089 (12)
C2	0.0701 (18)	0.0632 (19)	0.0639 (17)	0.0010 (14)	0.0119 (14)	0.0016 (14)
C3	0.077 (2)	0.076 (2)	0.093 (2)	0.0177 (17)	0.0258 (19)	0.0167 (18)
C4	0.0605 (19)	0.107 (3)	0.098 (3)	0.0091 (18)	0.0143 (18)	0.046 (2)
C5	0.079 (2)	0.110 (3)	0.086 (2)	−0.025 (2)	−0.0210 (18)	0.025 (2)
C6	0.089 (2)	0.0646 (19)	0.084 (2)	−0.0166 (16)	−0.0122 (18)	0.0074 (16)
C7	0.0505 (14)	0.0440 (14)	0.0622 (15)	−0.0018 (11)	0.0101 (12)	0.0037 (12)
C8	0.0616 (17)	0.0667 (18)	0.0794 (19)	0.0054 (14)	0.0177 (15)	0.0196 (15)
C9	0.0581 (18)	0.072 (2)	0.131 (3)	−0.0009 (15)	0.031 (2)	0.0299 (19)
C10	0.0476 (17)	0.069 (2)	0.136 (3)	−0.0007 (15)	0.0042 (19)	0.010 (2)
C11	0.0645 (19)	0.076 (2)	0.086 (2)	−0.0012 (16)	−0.0068 (16)	0.0027 (17)
C12	0.0594 (16)	0.0646 (17)	0.0673 (17)	−0.0032 (13)	0.0075 (13)	0.0034 (13)
C13	0.0568 (16)	0.0473 (15)	0.0599 (15)	−0.0101 (12)	0.0029 (12)	0.0041 (11)
C14	0.0604 (17)	0.0576 (17)	0.0724 (18)	−0.0102 (13)	0.0086 (14)	0.0010 (13)
C15	0.0655 (18)	0.0692 (19)	0.0760 (19)	−0.0166 (15)	0.0093 (15)	0.0024 (15)
C16	0.0727 (16)	0.0654 (16)	0.0598 (16)	−0.0262 (15)	0.0022 (13)	0.0002 (12)
C17	0.0739 (17)	0.0495 (16)	0.0790 (19)	−0.0023 (13)	0.0024 (14)	0.0040 (13)
C18	0.0679 (18)	0.0557 (17)	0.0778 (18)	−0.0030 (14)	0.0136 (14)	0.0061 (14)
C19	0.078 (2)	0.0675 (16)	0.080 (2)	−0.0169 (13)	−0.0011 (15)	0.0085 (14)
C20	0.081 (2)	0.0664 (16)	0.0682 (18)	−0.0164 (13)	−0.0052 (15)	0.0025 (13)
C21	0.0659 (17)	0.0672 (17)	0.0566 (16)	−0.0140 (14)	−0.0033 (14)	0.0054 (12)
C22	0.0665 (18)	0.0613 (18)	0.089 (2)	0.0021 (14)	−0.0002 (16)	0.0082 (16)
C23	0.0585 (18)	0.094 (3)	0.085 (2)	−0.0007 (17)	0.0104 (16)	0.0212 (19)
C24	0.0645 (18)	0.072 (2)	0.0670 (18)	−0.0163 (16)	−0.0075 (15)	0.0249 (15)
C25	0.103 (2)	0.0576 (18)	0.0674 (18)	−0.0071 (16)	−0.0012 (18)	0.0044 (15)
C26	0.095 (2)	0.068 (2)	0.0633 (17)	−0.0131 (17)	0.0124 (16)	−0.0006 (15)

O1—N2	1.168 (4)	C12—H12	0.9300
O2—N2	1.207 (4)	C13—C14	1.361 (4)
N1—C13	1.395 (3)	C13—C18	1.397 (4)
N1—C7	1.445 (3)	C14—C15	1.355 (4)
N1—C1	1.465 (3)	C14—H14	0.9300
N2—C24	1.454 (4)	C15—C16	1.390 (4)
C1—C2	1.373 (4)	C15—H15	0.9300
C1—C6	1.420 (4)	C16—C17	1.358 (4)
C2—C3	1.409 (4)	C16—C19	1.458 (4)
C2—H2	0.9300	C17—C18	1.375 (4)
C3—C4	1.410 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.367 (5)	C19—C20	1.276 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.422 (4)	C20—C21	1.463 (4)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.337 (4)
C7—C8	1.342 (3)	C21—C26	1.358 (4)
C7—C12	1.433 (4)	C22—C23	1.374 (4)
C8—C9	1.413 (4)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.356 (4)
C9—C10	1.401 (5)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.310 (4)
C10—C11	1.323 (4)	C25—C26	1.354 (4)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.402 (4)	C26—H26	0.9300
C11—H11	0.9300
C13—N1—C7	119.0 (2)	C14—C13—N1	119.2 (2)
C13—N1—C1	119.2 (2)	C14—C13—C18	118.6 (2)
C7—N1—C1	121.44 (19)	N1—C13—C18	122.2 (2)
O1—N2—O2	124.3 (4)	C15—C14—C13	119.2 (3)
O1—N2—C24	116.1 (4)	C15—C14—H14	120.4
O2—N2—C24	119.6 (4)	C13—C14—H14	120.4
C2—C1—C6	117.5 (3)	C14—C15—C16	122.9 (3)
C2—C1—N1	120.0 (2)	C14—C15—H15	118.6
C6—C1—N1	122.5 (2)	C16—C15—H15	118.6
C1—C2—C3	119.7 (3)	C17—C16—C15	118.0 (3)
C1—C2—H2	120.1	C17—C16—C19	121.3 (3)
C3—C2—H2	120.1	C15—C16—C19	120.6 (3)
C2—C3—C4	122.6 (3)	C16—C17—C18	119.7 (3)
C2—C3—H3	118.7	C16—C17—H17	120.1
C4—C3—H3	118.7	C18—C17—H17	120.1
C5—C4—C3	118.6 (3)	C17—C18—C13	121.3 (3)
C5—C4—H4	120.7	C17—C18—H18	119.4
C3—C4—H4	120.7	C13—C18—H18	119.4
C4—C5—C6	118.8 (3)	C20—C19—C16	129.0 (3)
C4—C5—H5	120.6	C20—C19—H19	115.5
C6—C5—H5	120.6	C16—C19—H19	115.5
C1—C6—C5	122.7 (3)	C19—C20—C21	128.2 (3)
C1—C6—H6	118.6	C19—C20—H20	115.9
C5—C6—H6	118.6	C21—C20—H20	115.9
C8—C7—C12	117.0 (2)	C22—C21—C26	117.3 (3)
C8—C7—N1	118.0 (2)	C22—C21—C20	122.1 (3)
C12—C7—N1	125.0 (2)	C26—C21—C20	120.6 (3)
C7—C8—C9	117.6 (3)	C21—C22—C23	119.4 (3)
C7—C8—H8	121.2	C21—C22—H22	120.3
C9—C8—H8	121.2	C23—C22—H22	120.3
C10—C9—C8	124.7 (3)	C24—C23—C22	120.6 (3)
C10—C9—H9	117.6	C24—C23—H23	119.7
C8—C9—H9	117.6	C22—C23—H23	119.7
C11—C10—C9	118.2 (3)	C25—C24—C23	121.2 (3)
C11—C10—H10	120.9	C25—C24—N2	117.1 (3)
C9—C10—H10	120.9	C23—C24—N2	121.8 (3)
C10—C11—C12	118.2 (3)	C24—C25—C26	117.3 (3)
C10—C11—H11	120.9	C24—C25—H25	121.4
C12—C11—H11	120.9	C26—C25—H25	121.4
C11—C12—C7	124.3 (3)	C25—C26—C21	124.2 (3)
C11—C12—H12	117.9	C25—C26—H26	117.9
C7—C12—H12	117.9	C21—C26—H26	117.9
C13—N1—C1—C2	129.1 (3)	C18—C13—C14—C15	4.5 (4)
C7—N1—C1—C2	−44.5 (3)	C13—C14—C15—C16	−0.7 (4)
C13—N1—C1—C6	−51.1 (3)	C14—C15—C16—C17	−3.4 (4)
C7—N1—C1—C6	135.3 (3)	C14—C15—C16—C19	173.8 (3)
C6—C1—C2—C3	0.0 (4)	C15—C16—C17—C18	3.5 (4)
N1—C1—C2—C3	179.7 (2)	C19—C16—C17—C18	−173.8 (3)
C1—C2—C3—C4	0.1 (4)	C16—C17—C18—C13	0.4 (4)
C2—C3—C4—C5	0.3 (5)	C14—C13—C18—C17	−4.5 (4)
C3—C4—C5—C6	−0.6 (5)	N1—C13—C18—C17	174.2 (2)
C2—C1—C6—C5	−0.4 (4)	C17—C16—C19—C20	−3.1 (5)
N1—C1—C6—C5	179.9 (3)	C15—C16—C19—C20	179.7 (3)
C4—C5—C6—C1	0.7 (5)	C16—C19—C20—C21	179.8 (3)
C13—N1—C7—C8	151.6 (2)	C19—C20—C21—C22	−29.6 (5)
C1—N1—C7—C8	−34.8 (3)	C19—C20—C21—C26	151.3 (3)
C13—N1—C7—C12	−28.3 (4)	C26—C21—C22—C23	−2.3 (4)
C1—N1—C7—C12	145.3 (2)	C20—C21—C22—C23	178.6 (3)
C12—C7—C8—C9	−0.2 (4)	C21—C22—C23—C24	−0.9 (4)
N1—C7—C8—C9	179.9 (2)	C22—C23—C24—C25	3.4 (5)
C7—C8—C9—C10	0.2 (5)	C22—C23—C24—N2	−175.9 (3)
C8—C9—C10—C11	0.6 (5)	O1—N2—C24—C25	176.1 (3)
C9—C10—C11—C12	−1.2 (5)	O2—N2—C24—C25	−3.6 (5)
C10—C11—C12—C7	1.1 (4)	O1—N2—C24—C23	−4.6 (5)
C8—C7—C12—C11	−0.4 (4)	O2—N2—C24—C23	175.7 (3)
N1—C7—C12—C11	179.5 (2)	C23—C24—C25—C26	−2.3 (5)
C7—N1—C13—C14	139.6 (3)	N2—C24—C25—C26	177.0 (3)
C1—N1—C13—C14	−34.2 (3)	C24—C25—C26—C21	−1.2 (5)
C7—N1—C13—C18	−39.1 (4)	C22—C21—C26—C25	3.5 (4)
C1—N1—C13—C18	147.1 (3)	C20—C21—C26—C25	−177.4 (3)
N1—C13—C14—C15	−174.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.58	3.481 (4)	162
C12—H12···O2ii	0.93	2.56	3.308 (4)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.58	3.481 (4)	162
C12—H12⋯O2ii	0.93	2.56	3.308 (4)	138

Symmetry codes: (i) ; (ii) .