(E,E)-N-[3-(Biphenyl-2-ylimino)butan-2-yl-idene]-2-phenyl-aniline.

The two C=N double bonds in the structure of the title compound, C(28)H(24)N(2), lie in the same plane with a bond length of 1.269 (2) Å. The mol-ecule is positioned on a centre of symmetry.

Related literature

For related literature, see: Bao et al. (2005 ▶); Bao, Lü et al. (2006 ▶); Bao, Ma et al. (2006 ▶); Zou et al. (2005 ▶).

Experimental

Crystal data

C28H24N2

M = 388.49

Monoclinic,

a = 9.603 (3) Å

b = 8.017 (3) Å

c = 14.332 (5) Å

β = 94.740 (6)°

V = 1099.7 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 273 (2) K

0.50 × 0.50 × 0.45 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.973, T max = 0.976

6608 measured reflections

2373 independent reflections

1776 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.178

S = 1.03

2373 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Bergerhoff, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003632/er2044sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003632/er2044Isup2.hkl

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

C28H24N2	F000 = 412
Mr = 388.49	Dx = 1.173 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 775 reflections
a = 9.603 (3) Å	θ = 2.7–26.1º
b = 8.017 (3) Å	µ = 0.07 mm−1
c = 14.332 (5) Å	T = 273 (2) K
β = 94.740 (6)º	Block, yellow
V = 1099.7 (7) Å3	0.50 × 0.50 × 0.45 mm
Z = 2

Bruker SMART 1K CCD diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 10 pixels mm-1	θmax = 27.0º
T = 273(2) K	θmin = 2.5º
ω scans	h = −12→12
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	k = −10→8
Tmin = 0.973, Tmax = 0.976	l = −15→18
6608 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.1119P)2 + 0.1177P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.27 e Å−3
2373 reflections	Δρmin = −0.19 e Å−3
137 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.126 (15)
Secondary atom site location: difference Fourier map

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
N1	0.41183 (12)	0.12272 (16)	0.07641 (9)	0.0549 (4)
C1	0.28095 (15)	0.14069 (18)	0.11538 (11)	0.0522 (4)
C2	0.26218 (19)	0.0733 (2)	0.20274 (12)	0.0678 (5)
H2A	0.3336	0.0117	0.2340	0.081*
C3	0.1387 (2)	0.0970 (2)	0.24353 (14)	0.0766 (6)
H3A	0.1269	0.0505	0.3018	0.092*
C4	0.03264 (19)	0.1895 (2)	0.19818 (14)	0.0728 (5)
H4A	−0.0501	0.2073	0.2261	0.087*
C5	0.05000 (16)	0.2551 (2)	0.11148 (13)	0.0626 (5)
H5A	−0.0224	0.3163	0.0810	0.075*
C6	0.17315 (14)	0.23261 (18)	0.06781 (10)	0.0513 (4)
C7	0.18618 (15)	0.30173 (19)	−0.02718 (10)	0.0540 (4)
C8	0.29127 (18)	0.4124 (2)	−0.04477 (12)	0.0638 (5)
H8A	0.3572	0.4420	0.0036	0.077*
C9	0.3002 (2)	0.4798 (3)	−0.13270 (13)	0.0799 (6)
H9A	0.3708	0.5554	−0.1429	0.096*
C10	0.2048 (3)	0.4352 (3)	−0.20518 (14)	0.0936 (8)
H10A	0.2104	0.4808	−0.2644	0.112*
C11	0.1018 (3)	0.3236 (3)	−0.18970 (15)	0.0941 (8)
H11A	0.0383	0.2920	−0.2391	0.113*
C12	0.09052 (19)	0.2568 (3)	−0.10133 (13)	0.0731 (5)
H12A	0.0191	0.1820	−0.0916	0.088*
C13	0.43020 (13)	0.00418 (18)	0.02004 (10)	0.0503 (4)
C14	0.32384 (18)	−0.1253 (3)	−0.00980 (15)	0.0783 (6)
H14C	0.3624	−0.2013	−0.0526	0.117*
H14B	0.2426	−0.0724	−0.0401	0.117*
H14A	0.2982	−0.1855	0.0441	0.117*

	U11	U22	U33	U12	U13	U23
N1	0.0449 (7)	0.0577 (7)	0.0620 (8)	0.0032 (5)	0.0036 (5)	−0.0031 (6)
C1	0.0450 (7)	0.0529 (8)	0.0590 (8)	−0.0012 (6)	0.0060 (6)	−0.0063 (6)
C2	0.0647 (10)	0.0702 (10)	0.0682 (10)	0.0027 (8)	0.0049 (8)	0.0078 (8)
C3	0.0831 (13)	0.0817 (12)	0.0680 (11)	−0.0117 (10)	0.0237 (9)	0.0057 (9)
C4	0.0608 (10)	0.0759 (11)	0.0854 (12)	−0.0047 (9)	0.0285 (9)	−0.0047 (9)
C5	0.0489 (9)	0.0618 (9)	0.0783 (11)	0.0025 (7)	0.0126 (7)	−0.0076 (7)
C6	0.0464 (8)	0.0481 (8)	0.0594 (8)	−0.0015 (6)	0.0056 (6)	−0.0090 (6)
C7	0.0503 (8)	0.0545 (8)	0.0570 (8)	0.0132 (6)	0.0045 (6)	−0.0080 (6)
C8	0.0706 (10)	0.0619 (10)	0.0605 (10)	0.0030 (8)	0.0155 (7)	−0.0056 (7)
C9	0.1029 (15)	0.0716 (11)	0.0695 (11)	0.0155 (10)	0.0331 (10)	0.0031 (9)
C10	0.128 (2)	0.0970 (16)	0.0586 (11)	0.0514 (15)	0.0237 (12)	0.0052 (10)
C11	0.1005 (16)	0.1150 (18)	0.0631 (12)	0.0464 (15)	−0.0156 (11)	−0.0194 (12)
C12	0.0634 (10)	0.0816 (12)	0.0721 (11)	0.0155 (9)	−0.0080 (8)	−0.0144 (9)
C13	0.0435 (8)	0.0497 (8)	0.0573 (8)	0.0037 (6)	0.0018 (6)	0.0011 (6)
C14	0.0592 (10)	0.0759 (12)	0.1026 (14)	−0.0153 (9)	0.0236 (9)	−0.0272 (10)

N1—C13	1.2691 (19)	C8—C9	1.380 (3)
N1—C1	1.424 (2)	C8—H8A	0.9300
C1—C2	1.389 (2)	C9—C10	1.374 (3)
C1—C6	1.401 (2)	C9—H9A	0.9300
C2—C3	1.378 (3)	C10—C11	1.365 (3)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.378 (3)	C11—C12	1.388 (3)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.372 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.494 (2)
C5—C6	1.395 (2)	C13—C13i	1.503 (3)
C5—H5A	0.9300	C14—H14C	0.9600
C6—C7	1.485 (2)	C14—H14B	0.9600
C7—C8	1.383 (2)	C14—H14A	0.9600
C7—C12	1.393 (2)
C13—N1—C1	119.94 (12)	C9—C8—H8A	119.4
C2—C1—C6	119.83 (14)	C7—C8—H8A	119.4
C2—C1—N1	119.91 (14)	C10—C9—C8	120.0 (2)
C6—C1—N1	120.19 (14)	C10—C9—H9A	120.0
C3—C2—C1	120.61 (16)	C8—C9—H9A	120.0
C3—C2—H2A	119.7	C11—C10—C9	119.61 (19)
C1—C2—H2A	119.7	C11—C10—H10A	120.2
C2—C3—C4	120.15 (17)	C9—C10—H10A	120.2
C2—C3—H3A	119.9	C10—C11—C12	120.9 (2)
C4—C3—H3A	119.9	C10—C11—H11A	119.5
C5—C4—C3	119.54 (16)	C12—C11—H11A	119.5
C5—C4—H4A	120.2	C11—C12—C7	120.0 (2)
C3—C4—H4A	120.2	C11—C12—H12A	120.0
C4—C5—C6	121.86 (16)	C7—C12—H12A	120.0
C4—C5—H5A	119.1	N1—C13—C14	125.10 (14)
C6—C5—H5A	119.1	N1—C13—C13i	116.87 (15)
C5—C6—C1	118.00 (15)	C14—C13—C13i	118.03 (16)
C5—C6—C7	120.13 (14)	C13—C14—H14C	109.5
C1—C6—C7	121.85 (13)	C13—C14—H14B	109.5
C8—C7—C12	118.16 (16)	H14C—C14—H14B	109.5
C8—C7—C6	121.66 (14)	C13—C14—H14A	109.5
C12—C7—C6	120.18 (16)	H14C—C14—H14A	109.5
C9—C8—C7	121.27 (18)	H14B—C14—H14A	109.5