(E)-N-[2-(Benzyl-iminometh-yl)phen-yl]-2,6-diisopropyl-aniline.

The mol-ecular conformation of the title compound, C(26)H(30)N(2), is reinforced by an intra-molecular N-H⋯N hydrogen bond, resulting in an almost planar [mean deviation of 0.023 (2) Å] S(6) ring. The dihedral angles between the central benzene ring and the terminal unsubstituted and substituted aromatic rings are 64.45 (9) and 89.40 (8)°, respectively.

Related literature

For background information on anilido-aldimine ligands, see: Lee et al. (2005 ▶); Yao et al. (2008 ▶). For related structures: see: Gao et al. (2008 ▶); Tsai et al. (2009 ▶).

Experimental

Crystal data

C26H30N2

M = 370.52

Triclinic,

a = 8.0583 (3) Å

b = 10.9186 (4) Å

c = 13.5974 (5) Å

α = 75.823 (2)°

β = 77.933 (2)°

γ = 82.709 (2)°

V = 1130.68 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.06 mm−1

T = 296 K

0.53 × 0.46 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.965, T max = 0.979

24959 measured reflections

5557 independent reflections

3150 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.178

S = 1.00

5557 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536809042202/hb5139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042202/hb5139Isup2.hkl

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

C26H30N2	Z = 2
Mr = 370.52	F(000) = 400
Triclinic, P1	Dx = 1.088 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0583 (3) Å	Cell parameters from 9972 reflections
b = 10.9186 (4) Å	θ = 2.2–28.2°
c = 13.5974 (5) Å	µ = 0.06 mm−1
α = 75.823 (2)°	T = 296 K
β = 77.933 (2)°	Block, colourless
γ = 82.709 (2)°	0.53 × 0.46 × 0.32 mm
V = 1130.68 (7) Å3

Bruker APEXII CCD diffractometer	5557 independent reflections
Radiation source: fine-focus sealed tube	3150 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 8.3333 pixels mm-1	θmax = 28.4°, θmin = 1.6°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −14→14
Tmin = 0.965, Tmax = 0.979	l = −18→18
24959 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/3
5557 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 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	0.46771 (17)	0.32146 (10)	0.01875 (8)	0.0622 (3)
N2	0.45207 (13)	0.23379 (11)	0.22480 (8)	0.0585 (3)
H2A	0.4023	0.2482	0.1725	0.070*
C1	0.62287 (15)	0.24628 (12)	0.20617 (10)	0.0514 (3)
C2	0.70993 (16)	0.28903 (12)	0.10401 (10)	0.0551 (3)
C3	0.8843 (2)	0.29836 (17)	0.08793 (13)	0.0797 (5)
H3A	0.9424	0.3256	0.0208	0.096*
C4	0.9738 (2)	0.26921 (19)	0.16647 (15)	0.0924 (6)
H4A	1.0904	0.2768	0.1532	0.111*
C5	0.8877 (2)	0.22822 (18)	0.26596 (15)	0.0870 (5)
H5A	0.9469	0.2089	0.3204	0.104*
C6	0.71649 (18)	0.21556 (15)	0.28577 (12)	0.0686 (4)
H6A	0.6615	0.1860	0.3533	0.082*
C7	0.6255 (2)	0.32311 (13)	0.01581 (11)	0.0642 (4)
H7A	0.6933	0.3485	−0.0488	0.077*
C8	0.4047 (2)	0.35949 (15)	−0.07799 (12)	0.0796 (5)
H8A	0.5003	0.3780	−0.1345	0.096*
H8B	0.3306	0.4368	−0.0778	0.096*
C9	0.30892 (18)	0.26118 (13)	−0.09649 (10)	0.0607 (4)
C10	0.2035 (2)	0.29393 (18)	−0.16839 (13)	0.0834 (5)
H10A	0.1899	0.3779	−0.2039	0.100*
C11	0.1182 (3)	0.2036 (2)	−0.18815 (17)	0.1083 (7)
H11A	0.0475	0.2272	−0.2368	0.130*
C12	0.1365 (3)	0.0791 (2)	−0.13670 (17)	0.1025 (6)
H12A	0.0798	0.0180	−0.1507	0.123*
C13	0.2379 (2)	0.04685 (17)	−0.06566 (15)	0.0885 (5)
H13A	0.2496	−0.0370	−0.0297	0.106*
C14	0.3242 (2)	0.13565 (14)	−0.04556 (11)	0.0695 (4)
H14A	0.3944	0.1108	0.0033	0.083*
C15	0.35020 (15)	0.19827 (12)	0.32539 (9)	0.0511 (3)
C16	0.32423 (16)	0.07005 (13)	0.36722 (10)	0.0559 (3)
C17	0.22163 (19)	0.03899 (15)	0.46347 (11)	0.0703 (4)
H17A	0.2019	−0.0454	0.4928	0.084*
C18	0.1483 (2)	0.13004 (18)	0.51657 (12)	0.0802 (5)
H18A	0.0799	0.1068	0.5813	0.096*
C19	0.1753 (2)	0.25461 (17)	0.47477 (12)	0.0782 (5)
H19A	0.1247	0.3155	0.5114	0.094*
C20	0.27753 (18)	0.29204 (14)	0.37815 (11)	0.0625 (4)
C21	0.3092 (3)	0.43053 (15)	0.33367 (15)	0.0877 (5)
H21A	0.3848	0.4336	0.2667	0.105*
C22	0.1524 (4)	0.5088 (2)	0.3115 (3)	0.1691 (13)
H22A	0.1784	0.5951	0.2822	0.254*
H22B	0.0705	0.5047	0.3744	0.254*
H22C	0.1064	0.4775	0.2636	0.254*
C23	0.4053 (6)	0.4786 (3)	0.3972 (3)	0.1996 (18)
H23A	0.4256	0.5657	0.3664	0.299*
H23B	0.5122	0.4291	0.4003	0.299*
H23C	0.3401	0.4719	0.4657	0.299*
C24	0.40181 (19)	−0.03072 (14)	0.30860 (13)	0.0717 (4)
H24A	0.5049	0.0004	0.2614	0.086*
C25	0.4532 (3)	−0.15552 (19)	0.3797 (2)	0.1265 (8)
H25A	0.5297	−0.1403	0.4201	0.190*
H25B	0.5087	−0.2145	0.3388	0.190*
H25C	0.3535	−0.1901	0.4247	0.190*
C26	0.2816 (3)	−0.0540 (2)	0.24438 (15)	0.1028 (6)
H26A	0.2491	0.0247	0.2003	0.154*
H26B	0.1820	−0.0891	0.2891	0.154*
H26C	0.3375	−0.1123	0.2030	0.154*

	U11	U22	U33	U12	U13	U23
N1	0.0752 (8)	0.0591 (7)	0.0527 (7)	−0.0122 (6)	−0.0189 (6)	−0.0042 (5)
N2	0.0467 (6)	0.0823 (8)	0.0450 (6)	−0.0171 (5)	−0.0106 (5)	−0.0034 (5)
C1	0.0459 (7)	0.0537 (7)	0.0546 (8)	−0.0083 (5)	−0.0080 (6)	−0.0113 (6)
C2	0.0547 (8)	0.0551 (7)	0.0545 (8)	−0.0105 (6)	−0.0037 (6)	−0.0124 (6)
C3	0.0557 (9)	0.1029 (12)	0.0750 (10)	−0.0197 (8)	0.0063 (8)	−0.0185 (9)
C4	0.0484 (9)	0.1297 (15)	0.0985 (14)	−0.0193 (9)	−0.0079 (9)	−0.0231 (12)
C5	0.0588 (10)	0.1167 (14)	0.0885 (12)	−0.0088 (9)	−0.0277 (9)	−0.0160 (10)
C6	0.0541 (9)	0.0904 (10)	0.0607 (9)	−0.0129 (7)	−0.0157 (7)	−0.0078 (7)
C7	0.0755 (10)	0.0643 (8)	0.0498 (8)	−0.0217 (7)	−0.0010 (7)	−0.0079 (6)
C8	0.1094 (13)	0.0708 (9)	0.0597 (9)	−0.0189 (9)	−0.0332 (9)	0.0041 (7)
C9	0.0649 (9)	0.0695 (9)	0.0463 (7)	0.0001 (6)	−0.0108 (6)	−0.0130 (6)
C10	0.0935 (12)	0.0892 (11)	0.0719 (10)	0.0053 (9)	−0.0353 (9)	−0.0155 (9)
C11	0.1071 (16)	0.1313 (19)	0.1084 (16)	0.0040 (13)	−0.0600 (13)	−0.0408 (14)
C12	0.0989 (15)	0.1114 (16)	0.1186 (17)	−0.0122 (12)	−0.0366 (13)	−0.0503 (13)
C13	0.0992 (13)	0.0763 (11)	0.0974 (13)	−0.0104 (9)	−0.0261 (11)	−0.0250 (10)
C14	0.0754 (10)	0.0696 (9)	0.0664 (9)	−0.0040 (7)	−0.0203 (8)	−0.0155 (7)
C15	0.0411 (6)	0.0669 (8)	0.0459 (7)	−0.0101 (5)	−0.0108 (5)	−0.0083 (6)
C16	0.0439 (7)	0.0666 (8)	0.0578 (8)	−0.0123 (6)	−0.0102 (6)	−0.0102 (6)
C17	0.0667 (9)	0.0768 (10)	0.0618 (9)	−0.0243 (7)	−0.0055 (7)	−0.0009 (7)
C18	0.0742 (10)	0.1087 (14)	0.0527 (9)	−0.0260 (9)	0.0057 (7)	−0.0138 (9)
C19	0.0754 (10)	0.0944 (12)	0.0675 (10)	−0.0056 (8)	−0.0022 (8)	−0.0332 (9)
C20	0.0596 (8)	0.0686 (8)	0.0609 (8)	−0.0075 (6)	−0.0127 (7)	−0.0148 (7)
C21	0.1018 (13)	0.0631 (9)	0.0948 (12)	−0.0060 (9)	−0.0115 (10)	−0.0175 (9)
C22	0.152 (2)	0.0931 (16)	0.229 (3)	0.0249 (16)	−0.043 (2)	0.0145 (19)
C23	0.305 (5)	0.0993 (17)	0.238 (4)	−0.079 (2)	−0.137 (4)	−0.013 (2)
C24	0.0598 (9)	0.0696 (9)	0.0848 (11)	−0.0114 (7)	−0.0024 (8)	−0.0220 (8)
C25	0.147 (2)	0.0824 (13)	0.158 (2)	0.0248 (12)	−0.0558 (17)	−0.0354 (14)
C26	0.0970 (13)	0.1335 (17)	0.0957 (13)	−0.0102 (11)	−0.0151 (11)	−0.0607 (12)

N1—C7	1.2659 (18)	C14—H14A	0.9300
N1—C8	1.4557 (17)	C15—C20	1.3921 (19)
N2—C1	1.3646 (16)	C15—C16	1.4006 (18)
N2—C15	1.4307 (16)	C16—C17	1.3831 (19)
N2—H2A	0.8600	C16—C24	1.511 (2)
C1—C6	1.3973 (18)	C17—C18	1.372 (2)
C1—C2	1.4134 (18)	C17—H17A	0.9300
C2—C3	1.389 (2)	C18—C19	1.366 (2)
C2—C7	1.449 (2)	C18—H18A	0.9300
C3—C4	1.364 (2)	C19—C20	1.393 (2)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.379 (2)	C20—C21	1.517 (2)
C4—H4A	0.9300	C21—C22	1.475 (3)
C5—C6	1.367 (2)	C21—C23	1.492 (3)
C5—H5A	0.9300	C21—H21A	0.9800
C6—H6A	0.9300	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C9	1.495 (2)	C22—H22C	0.9600
C8—H8A	0.9700	C23—H23A	0.9600
C8—H8B	0.9700	C23—H23B	0.9600
C9—C14	1.379 (2)	C23—H23C	0.9600
C9—C10	1.380 (2)	C24—C26	1.513 (2)
C10—C11	1.377 (3)	C24—C25	1.530 (3)
C10—H10A	0.9300	C24—H24A	0.9800
C11—C12	1.374 (3)	C25—H25A	0.9600
C11—H11A	0.9300	C25—H25B	0.9600
C12—C13	1.348 (3)	C25—H25C	0.9600
C12—H12A	0.9300	C26—H26A	0.9600
C13—C14	1.371 (2)	C26—H26B	0.9600
C13—H13A	0.9300	C26—H26C	0.9600
C7—N1—C8	118.36 (13)	C17—C16—C15	117.56 (13)
C1—N2—C15	124.45 (11)	C17—C16—C24	120.99 (13)
C1—N2—H2A	117.8	C15—C16—C24	121.43 (12)
C15—N2—H2A	117.8	C18—C17—C16	121.44 (14)
N2—C1—C6	121.68 (12)	C18—C17—H17A	119.3
N2—C1—C2	119.94 (12)	C16—C17—H17A	119.3
C6—C1—C2	118.37 (12)	C19—C18—C17	120.24 (14)
C3—C2—C1	118.26 (13)	C19—C18—H18A	119.9
C3—C2—C7	118.80 (13)	C17—C18—H18A	119.9
C1—C2—C7	122.93 (12)	C18—C19—C20	121.11 (15)
C4—C3—C2	122.75 (15)	C18—C19—H19A	119.4
C4—C3—H3A	118.6	C20—C19—H19A	119.4
C2—C3—H3A	118.6	C15—C20—C19	117.74 (14)
C3—C4—C5	118.60 (15)	C15—C20—C21	121.76 (13)
C3—C4—H4A	120.7	C19—C20—C21	120.49 (14)
C5—C4—H4A	120.7	C22—C21—C23	114.9 (2)
C6—C5—C4	120.95 (16)	C22—C21—C20	112.11 (18)
C6—C5—H5A	119.5	C23—C21—C20	111.35 (17)
C4—C5—H5A	119.5	C22—C21—H21A	105.9
C5—C6—C1	121.06 (14)	C23—C21—H21A	105.9
C5—C6—H6A	119.5	C20—C21—H21A	105.9
C1—C6—H6A	119.5	C21—C22—H22A	109.5
N1—C7—C2	125.85 (13)	C21—C22—H22B	109.5
N1—C7—H7A	117.1	H22A—C22—H22B	109.5
C2—C7—H7A	117.1	C21—C22—H22C	109.5
N1—C8—C9	113.42 (12)	H22A—C22—H22C	109.5
N1—C8—H8A	108.9	H22B—C22—H22C	109.5
C9—C8—H8A	108.9	C21—C23—H23A	109.5
N1—C8—H8B	108.9	C21—C23—H23B	109.5
C9—C8—H8B	108.9	H23A—C23—H23B	109.5
H8A—C8—H8B	107.7	C21—C23—H23C	109.5
C14—C9—C10	117.49 (14)	H23A—C23—H23C	109.5
C14—C9—C8	122.37 (13)	H23B—C23—H23C	109.5
C10—C9—C8	120.13 (13)	C16—C24—C26	110.94 (13)
C11—C10—C9	120.70 (17)	C16—C24—C25	112.51 (15)
C11—C10—H10A	119.7	C26—C24—C25	109.81 (16)
C9—C10—H10A	119.7	C16—C24—H24A	107.8
C12—C11—C10	120.62 (18)	C26—C24—H24A	107.8
C12—C11—H11A	119.7	C25—C24—H24A	107.8
C10—C11—H11A	119.7	C24—C25—H25A	109.5
C13—C12—C11	118.89 (18)	C24—C25—H25B	109.5
C13—C12—H12A	120.6	H25A—C25—H25B	109.5
C11—C12—H12A	120.6	C24—C25—H25C	109.5
C12—C13—C14	121.10 (18)	H25A—C25—H25C	109.5
C12—C13—H13A	119.5	H25B—C25—H25C	109.5
C14—C13—H13A	119.5	C24—C26—H26A	109.5
C13—C14—C9	121.20 (15)	C24—C26—H26B	109.5
C13—C14—H14A	119.4	H26A—C26—H26B	109.5
C9—C14—H14A	119.4	C24—C26—H26C	109.5
C20—C15—C16	121.90 (12)	H26A—C26—H26C	109.5
C20—C15—N2	119.19 (12)	H26B—C26—H26C	109.5
C16—C15—N2	118.90 (12)
C15—N2—C1—C6	4.9 (2)	C8—C9—C14—C13	−178.51 (16)
C15—N2—C1—C2	−176.32 (12)	C1—N2—C15—C20	88.21 (16)
N2—C1—C2—C3	−178.86 (12)	C1—N2—C15—C16	−92.83 (15)
C6—C1—C2—C3	−0.01 (19)	C20—C15—C16—C17	0.5 (2)
N2—C1—C2—C7	1.0 (2)	N2—C15—C16—C17	−178.38 (11)
C6—C1—C2—C7	179.87 (12)	C20—C15—C16—C24	179.15 (13)
C1—C2—C3—C4	−0.6 (2)	N2—C15—C16—C24	0.22 (18)
C7—C2—C3—C4	179.48 (16)	C15—C16—C17—C18	−0.3 (2)
C2—C3—C4—C5	0.3 (3)	C24—C16—C17—C18	−178.90 (14)
C3—C4—C5—C6	0.7 (3)	C16—C17—C18—C19	0.1 (3)
C4—C5—C6—C1	−1.4 (3)	C17—C18—C19—C20	−0.2 (3)
N2—C1—C6—C5	179.82 (14)	C16—C15—C20—C19	−0.6 (2)
C2—C1—C6—C5	1.0 (2)	N2—C15—C20—C19	178.32 (12)
C8—N1—C7—C2	179.73 (13)	C16—C15—C20—C21	178.58 (13)
C3—C2—C7—N1	−178.73 (13)	N2—C15—C20—C21	−2.5 (2)
C1—C2—C7—N1	1.4 (2)	C18—C19—C20—C15	0.4 (2)
C7—N1—C8—C9	124.20 (15)	C18—C19—C20—C21	−178.78 (15)
N1—C8—C9—C14	−19.0 (2)	C15—C20—C21—C22	115.1 (2)
N1—C8—C9—C10	162.48 (14)	C19—C20—C21—C22	−65.7 (3)
C14—C9—C10—C11	−0.3 (2)	C15—C20—C21—C23	−114.7 (3)
C8—C9—C10—C11	178.24 (18)	C19—C20—C21—C23	64.5 (3)
C9—C10—C11—C12	−0.1 (3)	C17—C16—C24—C26	87.45 (18)
C10—C11—C12—C13	0.7 (3)	C15—C16—C24—C26	−91.11 (17)
C11—C12—C13—C14	−1.0 (3)	C17—C16—C24—C25	−36.0 (2)
C12—C13—C14—C9	0.7 (3)	C15—C16—C24—C25	145.44 (16)
C10—C9—C14—C13	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.03	2.7113 (15)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.86	2.03	2.7113 (15)	136