2-{[(Biphenyl-2-yl)diazen-yl]methyl-idene}-1,3,3-trimethyl-indoline.

The title mol-ecule, C(24)H(23)N(3), shows some delocalization of charge based on the small [8.0 (2)°] angle between the indolin-2-yl-idene ring system and the link methyl-diazene C(2)N(2) atom plane. A further twist of 17.2 (3)° is subtended between the C(2)N(2) plane and its attached benzene ring. The dihedral angle between the biphenyl rings is 47.96(14)°. In the crystal, the mol-ecules pack via C-H⋯π attractive inter-actions.

Related literature

For applications of azo compounds, see: Möhlmann & van der Vorst (1989 ▶); Zollinger (1987 ▶). For related compounds, see Jones (2004 ▶); Jones & Chrapkowski (2004 ▶); Gainsford et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C24H23N3

M = 353.45

Orthorhombic,

a = 14.2968 (17) Å

b = 8.2407 (10) Å

c = 16.2671 (17) Å

V = 1916.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 116 K

0.70 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan [Blessing (1995 ▶) and SADABS (Bruker, 2005 ▶)] T min = 0.640, T max = 0.746

34258 measured reflections

1783 independent reflections

1764 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.23

1783 reflections

247 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008890/ez2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008890/ez2238Isup2.hkl

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

C24H23N3	F(000) = 752
Mr = 353.45	Dx = 1.225 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9914 reflections
a = 14.2968 (17) Å	θ = 2.5–27.3°
b = 8.2407 (10) Å	µ = 0.07 mm−1
c = 16.2671 (17) Å	T = 116 K
V = 1916.5 (4) Å3	Needle, red
Z = 4	0.70 × 0.20 × 0.10 mm

Bruker APEXII CCD diffractometer	1783 independent reflections
graphite	1764 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm-1	Rint = 0.041
φ and ω scans	θmax = 25.2°, θmin = 2.5°
Absorption correction: multi-scan [Blessing (1995) and SADABS (Bruker, 2005)]	h = −17→17
Tmin = 0.640, Tmax = 0.746	k = −9→9
34258 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.23	w = 1/[σ2(Fo2) + (0.0282P)2 + 0.7948P] where P = (Fo2 + 2Fc2)/3
1783 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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	0.78152 (16)	1.0321 (3)	0.45002 (13)	0.0248 (5)
N2	0.64108 (16)	0.6649 (3)	0.43989 (14)	0.0238 (5)
N3	0.58268 (16)	0.6112 (3)	0.38682 (14)	0.0261 (5)
C1	0.7761 (2)	1.1095 (4)	0.36962 (19)	0.0333 (7)
H1A	0.7164	1.1669	0.3645	0.050*
H1B	0.7806	1.0267	0.3266	0.050*
H1C	0.8277	1.1869	0.3637	0.050*
C2	0.73892 (18)	0.8894 (3)	0.47008 (16)	0.0216 (6)
C3	0.76949 (18)	0.8406 (3)	0.55730 (17)	0.0235 (6)
C4	0.83106 (18)	0.9831 (3)	0.58035 (17)	0.0250 (6)
C5	0.8798 (2)	1.0170 (4)	0.6516 (2)	0.0376 (7)
H5	0.8786	0.9433	0.6965	0.045*
C6	0.9309 (2)	1.1616 (4)	0.6568 (2)	0.0444 (9)
H6	0.9645	1.1863	0.7056	0.053*
C7	0.9329 (2)	1.2686 (4)	0.5914 (2)	0.0421 (8)
H7	0.9679	1.3663	0.5962	0.050*
C8	0.8851 (2)	1.2369 (4)	0.5189 (2)	0.0349 (7)
H8	0.8866	1.3101	0.4738	0.042*
C9	0.83496 (19)	1.0929 (3)	0.51568 (18)	0.0258 (6)
C10	0.6853 (2)	0.8259 (4)	0.61544 (18)	0.0321 (7)
H10A	0.6504	0.9283	0.6157	0.048*
H10B	0.7073	0.8019	0.6712	0.048*
H10C	0.6443	0.7381	0.5965	0.048*
C11	0.8248 (2)	0.6797 (3)	0.55651 (19)	0.0276 (6)
H11A	0.8479	0.6563	0.6120	0.041*
H11B	0.8778	0.6891	0.5187	0.041*
H11C	0.7837	0.5914	0.5384	0.041*
C12	0.67785 (19)	0.8119 (3)	0.41935 (17)	0.0245 (6)
H12	0.6606	0.8612	0.3688	0.029*
C13	0.55193 (18)	0.4505 (3)	0.40219 (17)	0.0240 (6)
C14	0.5934 (2)	0.3493 (4)	0.46096 (19)	0.0312 (7)
H14	0.6403	0.3914	0.4964	0.037*
C15	0.5666 (2)	0.1883 (3)	0.46788 (19)	0.0316 (7)
H15	0.5948	0.1210	0.5083	0.038*
C16	0.4991 (2)	0.1253 (3)	0.4164 (2)	0.0323 (7)
H16	0.4833	0.0135	0.4191	0.039*
C17	0.4546 (2)	0.2260 (3)	0.36077 (18)	0.0282 (6)
H17	0.4065	0.1826	0.3271	0.034*
C18	0.47830 (19)	0.3887 (3)	0.35274 (16)	0.0245 (6)
C19	0.42423 (19)	0.4918 (3)	0.29410 (17)	0.0247 (6)
C20	0.32655 (19)	0.4815 (3)	0.29415 (18)	0.0280 (6)
H20	0.2962	0.4128	0.3327	0.034*
C21	0.2735 (2)	0.5700 (4)	0.23883 (19)	0.0336 (7)
H21	0.2073	0.5609	0.2397	0.040*
C22	0.3156 (2)	0.6708 (4)	0.1826 (2)	0.0371 (7)
H22	0.2789	0.7308	0.1446	0.045*
C23	0.4127 (2)	0.6838 (4)	0.18199 (19)	0.0367 (8)
H23	0.4424	0.7541	0.1438	0.044*
C24	0.4663 (2)	0.5949 (4)	0.23681 (18)	0.0304 (7)
H24	0.5325	0.6041	0.2354	0.036*

	U11	U22	U33	U12	U13	U23
N1	0.0280 (12)	0.0215 (11)	0.0248 (12)	0.0027 (9)	0.0003 (9)	0.0034 (10)
N2	0.0218 (11)	0.0250 (12)	0.0247 (11)	0.0029 (9)	−0.0005 (9)	−0.0013 (10)
N3	0.0282 (12)	0.0252 (12)	0.0248 (12)	0.0016 (10)	−0.0049 (10)	−0.0008 (10)
C1	0.0377 (16)	0.0289 (15)	0.0334 (16)	0.0005 (13)	0.0023 (13)	0.0120 (14)
C2	0.0218 (13)	0.0214 (12)	0.0216 (13)	0.0049 (11)	0.0021 (11)	0.0014 (12)
C3	0.0247 (14)	0.0243 (13)	0.0215 (13)	0.0042 (11)	−0.0006 (11)	0.0012 (12)
C4	0.0201 (13)	0.0302 (15)	0.0249 (13)	0.0072 (11)	0.0024 (11)	−0.0055 (12)
C5	0.0318 (16)	0.0471 (18)	0.0339 (16)	0.0055 (14)	−0.0057 (14)	−0.0054 (16)
C6	0.0334 (17)	0.056 (2)	0.0438 (19)	0.0024 (15)	−0.0076 (15)	−0.0196 (18)
C7	0.0269 (16)	0.0374 (18)	0.062 (2)	−0.0023 (14)	0.0000 (15)	−0.0175 (17)
C8	0.0273 (16)	0.0272 (15)	0.0502 (18)	0.0014 (12)	0.0067 (14)	−0.0066 (15)
C9	0.0210 (13)	0.0241 (14)	0.0324 (14)	0.0034 (11)	0.0036 (12)	−0.0065 (13)
C10	0.0287 (15)	0.0413 (18)	0.0264 (15)	0.0042 (14)	0.0048 (12)	0.0063 (13)
C11	0.0279 (14)	0.0273 (14)	0.0276 (14)	0.0031 (12)	−0.0016 (12)	0.0065 (13)
C12	0.0285 (14)	0.0228 (14)	0.0220 (13)	0.0030 (11)	−0.0004 (11)	0.0031 (11)
C13	0.0248 (14)	0.0238 (13)	0.0234 (13)	0.0049 (11)	0.0057 (11)	−0.0019 (11)
C14	0.0301 (15)	0.0330 (16)	0.0305 (15)	0.0051 (12)	0.0007 (13)	−0.0011 (13)
C15	0.0336 (16)	0.0267 (15)	0.0345 (16)	0.0106 (12)	0.0096 (13)	0.0099 (14)
C16	0.0336 (16)	0.0243 (14)	0.0391 (16)	0.0006 (13)	0.0152 (13)	0.0016 (14)
C17	0.0255 (14)	0.0287 (15)	0.0304 (15)	−0.0037 (12)	0.0087 (12)	−0.0015 (12)
C18	0.0254 (14)	0.0269 (14)	0.0211 (13)	0.0014 (11)	0.0088 (11)	−0.0003 (11)
C19	0.0286 (14)	0.0238 (13)	0.0217 (13)	−0.0018 (11)	0.0002 (12)	−0.0067 (12)
C20	0.0288 (15)	0.0272 (15)	0.0282 (14)	−0.0041 (12)	0.0000 (13)	−0.0076 (13)
C21	0.0303 (16)	0.0348 (16)	0.0356 (16)	0.0009 (13)	−0.0067 (13)	−0.0118 (14)
C22	0.0432 (18)	0.0377 (17)	0.0304 (16)	0.0063 (15)	−0.0137 (14)	−0.0030 (14)
C23	0.0448 (19)	0.0423 (19)	0.0230 (15)	−0.0037 (15)	−0.0044 (14)	0.0070 (14)
C24	0.0287 (15)	0.0367 (17)	0.0258 (14)	−0.0031 (13)	0.0032 (12)	−0.0005 (13)

N1—C2	1.364 (3)	C11—H11A	0.9800
N1—C9	1.405 (4)	C11—H11B	0.9800
N1—C1	1.457 (4)	C11—H11C	0.9800
N2—N3	1.280 (3)	C12—H12	0.9500
N2—C12	1.362 (4)	C13—C14	1.400 (4)
N3—C13	1.418 (4)	C13—C18	1.419 (4)
C1—H1A	0.9800	C14—C15	1.386 (4)
C1—H1B	0.9800	C14—H14	0.9500
C1—H1C	0.9800	C15—C16	1.379 (5)
C2—C12	1.361 (4)	C15—H15	0.9500
C2—C3	1.538 (4)	C16—C17	1.383 (4)
C3—C4	1.515 (4)	C16—H16	0.9500
C3—C10	1.536 (4)	C17—C18	1.389 (4)
C3—C11	1.544 (4)	C17—H17	0.9500
C4—C5	1.381 (4)	C18—C19	1.493 (4)
C4—C9	1.388 (4)	C19—C24	1.397 (4)
C5—C6	1.401 (5)	C19—C20	1.399 (4)
C5—H5	0.9500	C20—C21	1.384 (4)
C6—C7	1.381 (5)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.375 (5)
C7—C8	1.389 (5)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.392 (5)
C8—C9	1.388 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.385 (4)
C10—H10A	0.9800	C23—H23	0.9500
C10—H10B	0.9800	C24—H24	0.9500
C10—H10C	0.9800
C2—N1—C9	111.6 (2)	C3—C11—H11B	109.5
C2—N1—C1	124.6 (2)	H11A—C11—H11B	109.5
C9—N1—C1	123.7 (2)	C3—C11—H11C	109.5
N3—N2—C12	113.2 (2)	H11A—C11—H11C	109.5
N2—N3—C13	114.0 (2)	H11B—C11—H11C	109.5
N1—C1—H1A	109.5	C2—C12—N2	121.1 (2)
N1—C1—H1B	109.5	C2—C12—H12	119.5
H1A—C1—H1B	109.5	N2—C12—H12	119.5
N1—C1—H1C	109.5	C14—C13—N3	123.0 (3)
H1A—C1—H1C	109.5	C14—C13—C18	119.2 (3)
H1B—C1—H1C	109.5	N3—C13—C18	117.7 (2)
C12—C2—N1	123.1 (2)	C15—C14—C13	120.6 (3)
C12—C2—C3	128.3 (2)	C15—C14—H14	119.7
N1—C2—C3	108.6 (2)	C13—C14—H14	119.7
C4—C3—C10	111.4 (2)	C16—C15—C14	120.3 (3)
C4—C3—C2	101.0 (2)	C16—C15—H15	119.8
C10—C3—C2	111.5 (2)	C14—C15—H15	119.8
C4—C3—C11	111.8 (2)	C15—C16—C17	119.6 (3)
C10—C3—C11	109.8 (2)	C15—C16—H16	120.2
C2—C3—C11	111.3 (2)	C17—C16—H16	120.2
C5—C4—C9	119.0 (3)	C16—C17—C18	121.9 (3)
C5—C4—C3	131.1 (3)	C16—C17—H17	119.0
C9—C4—C3	109.9 (2)	C18—C17—H17	119.0
C4—C5—C6	119.0 (3)	C17—C18—C13	118.3 (3)
C4—C5—H5	120.5	C17—C18—C19	118.9 (3)
C6—C5—H5	120.5	C13—C18—C19	122.8 (2)
C7—C6—C5	120.5 (3)	C24—C19—C20	117.8 (3)
C7—C6—H6	119.7	C24—C19—C18	123.3 (2)
C5—C6—H6	119.7	C20—C19—C18	118.8 (3)
C6—C7—C8	121.6 (3)	C21—C20—C19	120.9 (3)
C6—C7—H7	119.2	C21—C20—H20	119.5
C8—C7—H7	119.2	C19—C20—H20	119.5
C9—C8—C7	116.6 (3)	C22—C21—C20	120.8 (3)
C9—C8—H8	121.7	C22—C21—H21	119.6
C7—C8—H8	121.7	C20—C21—H21	119.6
C8—C9—C4	123.3 (3)	C21—C22—C23	119.2 (3)
C8—C9—N1	127.9 (3)	C21—C22—H22	120.4
C4—C9—N1	108.8 (2)	C23—C22—H22	120.4
C3—C10—H10A	109.5	C24—C23—C22	120.4 (3)
C3—C10—H10B	109.5	C24—C23—H23	119.8
H10A—C10—H10B	109.5	C22—C23—H23	119.8
C3—C10—H10C	109.5	C23—C24—C19	120.9 (3)
H10A—C10—H10C	109.5	C23—C24—H24	119.6
H10B—C10—H10C	109.5	C19—C24—H24	119.6
C3—C11—H11A	109.5
C12—N2—N3—C13	173.1 (2)	C2—N1—C9—C4	2.7 (3)
C9—N1—C2—C12	175.1 (2)	C1—N1—C9—C4	−174.8 (2)
C1—N1—C2—C12	−7.4 (4)	N1—C2—C12—N2	176.2 (2)
C9—N1—C2—C3	−3.1 (3)	C3—C2—C12—N2	−6.1 (4)
C1—N1—C2—C3	174.4 (2)	N3—N2—C12—C2	177.9 (2)
C12—C2—C3—C4	−175.8 (3)	N2—N3—C13—C14	−10.7 (4)
N1—C2—C3—C4	2.2 (3)	N2—N3—C13—C18	172.1 (2)
C12—C2—C3—C10	−57.5 (4)	N3—C13—C14—C15	−173.7 (3)
N1—C2—C3—C10	120.6 (3)	C18—C13—C14—C15	3.5 (4)
C12—C2—C3—C11	65.5 (3)	C13—C14—C15—C16	0.5 (4)
N1—C2—C3—C11	−116.5 (2)	C14—C15—C16—C17	−3.5 (4)
C10—C3—C4—C5	60.5 (4)	C15—C16—C17—C18	2.5 (4)
C2—C3—C4—C5	179.0 (3)	C16—C17—C18—C13	1.5 (4)
C11—C3—C4—C5	−62.7 (4)	C16—C17—C18—C19	−177.2 (2)
C10—C3—C4—C9	−119.1 (2)	C14—C13—C18—C17	−4.4 (4)
C2—C3—C4—C9	−0.6 (3)	N3—C13—C18—C17	172.9 (2)
C11—C3—C4—C9	117.7 (3)	C14—C13—C18—C19	174.2 (3)
C9—C4—C5—C6	0.5 (4)	N3—C13—C18—C19	−8.5 (4)
C3—C4—C5—C6	−179.0 (3)	C17—C18—C19—C24	−132.0 (3)
C4—C5—C6—C7	−0.2 (5)	C13—C18—C19—C24	49.4 (4)
C5—C6—C7—C8	−0.2 (5)	C17—C18—C19—C20	45.8 (4)
C6—C7—C8—C9	0.3 (4)	C13—C18—C19—C20	−132.8 (3)
C7—C8—C9—C4	0.1 (4)	C24—C19—C20—C21	0.4 (4)
C7—C8—C9—N1	−179.6 (3)	C18—C19—C20—C21	−177.5 (3)
C5—C4—C9—C8	−0.5 (4)	C19—C20—C21—C22	−0.2 (4)
C3—C4—C9—C8	179.2 (2)	C20—C21—C22—C23	−0.3 (5)
C5—C4—C9—N1	179.3 (2)	C21—C22—C23—C24	0.7 (5)
C3—C4—C9—N1	−1.1 (3)	C22—C23—C24—C19	−0.6 (5)
C2—N1—C9—C8	−177.6 (3)	C20—C19—C24—C23	0.0 (4)
C1—N1—C9—C8	4.9 (4)	C18—C19—C24—C23	177.8 (3)

Cg1, Cg2 and Cg3 are the centroids of the C19–C24, C4–C9 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cg1i	0.98	2.86	3.582 (3)	131
C1—H1A···Cg1ii	0.98	3.02	3.948 (3)	160
C11—H11B···Cg3iii	0.98	2.74	3.721 (3)	179
C22—H22···Cg2iv	0.95	2.76	3.645 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C19–C24, C4–C9 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cg1i	0.98	2.86	3.582 (3)	131
C11—H11B⋯Cg3ii	0.98	2.74	3.721 (3)	179
C22—H22⋯Cg2iii	0.95	2.76	3.645 (3)	155

Symmetry codes: (i) ; (ii) ; (iii) .