2-[(2,6-Diethyl-phen-yl)imino-meth-yl]-N-(2-methoxy-phen-yl)aniline.

The title anilide-imine compound, C(24)H(26)N(2)O, features an intra-molecular N-H⋯N hydrogen bond involving the imine and anilide groups to generate an S(6) ring motif. The mol-ecule displays an E configuration about the imine C=N double bond, with the dihedral angle between the two benzene rings being 86.5°. The packing is stabilized by three different C-H⋯π inter-actions.

Related literature

For related background on anilido–imine complexes, see: Liu et al. (2005 ▶, 2006 ▶); Ren et al. (2007 ▶); Su et al. (2007 ▶); Yao et al. (2008 ▶); Wang et al. (2006 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H26N2O

M = 358.47

Monoclinic,

a = 12.930 (3) Å

b = 7.4757 (15) Å

c = 21.303 (4) Å

β = 97.88 (3)°

V = 2039.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.44 × 0.40 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.969, T max = 0.986

19406 measured reflections

4670 independent reflections

3515 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.06

4670 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037969/fl2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037969/fl2258Isup2.hkl

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

C24H26N2O	F(000) = 768
Mr = 358.47	Dx = 1.167 Mg m−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.930 (3) Å	Cell parameters from 14731 reflections
b = 7.4757 (15) Å	θ = 3.2–27.5°
c = 21.303 (4) Å	µ = 0.07 mm−1
β = 97.88 (3)°	T = 295 K
V = 2039.7 (7) Å3	Block, yellow
Z = 4	0.44 × 0.40 × 0.19 mm

Rigaku R-AXIS RAPID diffractometer	4670 independent reflections
Radiation source: fine-focus sealed tube	3515 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.969, Tmax = 0.986	k = −9→9
19406 measured reflections	l = −27→27

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2475P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4670 reflections	Δρmax = 0.19 e Å−3
252 parameters	Δρmin = −0.17 e Å−3
0 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: 0.0251 (17)

Experimental. (See detailed section in the paper)

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	0.52847 (8)	1.56960 (13)	0.17089 (5)	0.0608 (3)
N1	0.28321 (8)	0.98441 (15)	0.08469 (5)	0.0460 (3)
N2	0.12969 (8)	0.75355 (13)	0.10555 (5)	0.0405 (2)
C1	0.28918 (8)	0.88995 (15)	0.03007 (5)	0.0363 (3)
C2	0.22193 (8)	0.74272 (15)	0.01420 (5)	0.0367 (3)
C3	0.22900 (9)	0.64858 (17)	−0.04164 (6)	0.0436 (3)
H3	0.1840	0.5530	−0.0523	0.052*
C4	0.30038 (10)	0.69250 (19)	−0.08147 (6)	0.0507 (3)
H4	0.3037	0.6282	−0.1185	0.061*
C5	0.36708 (10)	0.83456 (19)	−0.06505 (6)	0.0500 (3)
H5	0.4164	0.8647	−0.0912	0.060*
C6	0.36198 (9)	0.93198 (17)	−0.01092 (6)	0.0443 (3)
H6	0.4075	1.0274	−0.0012	0.053*
C7	0.14318 (9)	0.68530 (16)	0.05253 (5)	0.0390 (3)
H7	0.0994	0.5918	0.0372	0.047*
C8	0.04576 (9)	0.68824 (16)	0.13614 (5)	0.0392 (3)
C9	0.06378 (10)	0.54991 (16)	0.18027 (6)	0.0455 (3)
C10	−0.01957 (12)	0.49231 (18)	0.21017 (7)	0.0554 (4)
H10	−0.0096	0.3997	0.2395	0.067*
C11	−0.11638 (12)	0.5703 (2)	0.19697 (7)	0.0582 (4)
H11	−0.1714	0.5293	0.2170	0.070*
C12	−0.13204 (10)	0.7088 (2)	0.15432 (7)	0.0535 (4)
H12	−0.1978	0.7610	0.1461	0.064*
C13	−0.05162 (9)	0.77272 (17)	0.12316 (6)	0.0439 (3)
C14	0.17116 (13)	0.4706 (2)	0.19727 (7)	0.0612 (4)
H14A	0.2026	0.4539	0.1589	0.073*
H14B	0.1649	0.3540	0.2164	0.073*
C15	0.24158 (13)	0.5868 (3)	0.24255 (9)	0.0841 (5)
H15A	0.2506	0.7006	0.2231	0.126*
H15B	0.3082	0.5296	0.2528	0.126*
H15C	0.2107	0.6041	0.2806	0.126*
C16	−0.06704 (11)	0.9317 (2)	0.07983 (7)	0.0566 (4)
H16A	−0.1412	0.9560	0.0700	0.068*
H16B	−0.0408	0.9033	0.0405	0.068*
C17	−0.01226 (13)	1.0986 (2)	0.10827 (9)	0.0700 (4)
H17A	−0.0415	1.1328	0.1455	0.105*
H17B	−0.0215	1.1940	0.0779	0.105*
H17C	0.0609	1.0744	0.1194	0.105*
C18	0.34258 (9)	1.13770 (16)	0.10489 (6)	0.0398 (3)
C19	0.39696 (10)	1.14282 (17)	0.16584 (6)	0.0452 (3)
H19	0.3931	1.0463	0.1929	0.054*
C20	0.45650 (10)	1.28936 (18)	0.18645 (6)	0.0487 (3)
H20	0.4920	1.2915	0.2275	0.058*
C21	0.46397 (9)	1.43359 (17)	0.14663 (6)	0.0434 (3)
C22	0.40796 (10)	1.43273 (17)	0.08638 (6)	0.0455 (3)
H22	0.4112	1.5299	0.0595	0.055*
C23	0.34714 (9)	1.28581 (17)	0.06663 (6)	0.0445 (3)
H23	0.3083	1.2867	0.0265	0.053*
C24	0.54257 (13)	1.7158 (2)	0.13088 (9)	0.0701 (5)
H24A	0.5698	1.6736	0.0938	0.105*
H24B	0.5908	1.7992	0.1531	0.105*
H24C	0.4767	1.7739	0.1185	0.105*
H1	0.2406 (11)	0.937 (2)	0.1104 (7)	0.056 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0714 (6)	0.0509 (6)	0.0578 (6)	−0.0154 (5)	0.0004 (5)	−0.0115 (5)
N1	0.0485 (6)	0.0493 (6)	0.0423 (6)	−0.0118 (5)	0.0134 (5)	−0.0073 (5)
N2	0.0442 (5)	0.0395 (5)	0.0387 (5)	−0.0029 (4)	0.0090 (4)	0.0020 (4)
C1	0.0339 (5)	0.0391 (6)	0.0354 (6)	0.0038 (4)	0.0026 (4)	0.0005 (5)
C2	0.0359 (5)	0.0382 (6)	0.0355 (6)	0.0032 (5)	0.0035 (5)	0.0024 (5)
C3	0.0442 (6)	0.0432 (7)	0.0432 (6)	0.0000 (5)	0.0051 (5)	−0.0054 (5)
C4	0.0533 (7)	0.0565 (8)	0.0442 (7)	0.0027 (6)	0.0135 (6)	−0.0108 (6)
C5	0.0448 (7)	0.0593 (8)	0.0491 (7)	0.0014 (6)	0.0179 (6)	−0.0019 (6)
C6	0.0372 (6)	0.0471 (7)	0.0498 (7)	−0.0025 (5)	0.0100 (5)	−0.0018 (6)
C7	0.0407 (6)	0.0356 (6)	0.0403 (6)	−0.0022 (5)	0.0040 (5)	0.0010 (5)
C8	0.0452 (6)	0.0371 (6)	0.0364 (6)	−0.0069 (5)	0.0096 (5)	−0.0048 (5)
C9	0.0601 (7)	0.0365 (6)	0.0422 (7)	−0.0020 (5)	0.0155 (6)	−0.0023 (5)
C10	0.0805 (10)	0.0415 (7)	0.0488 (7)	−0.0124 (7)	0.0252 (7)	−0.0025 (6)
C11	0.0649 (9)	0.0601 (9)	0.0549 (8)	−0.0248 (7)	0.0274 (7)	−0.0164 (7)
C12	0.0436 (7)	0.0638 (9)	0.0543 (8)	−0.0100 (6)	0.0105 (6)	−0.0166 (7)
C13	0.0430 (6)	0.0475 (7)	0.0403 (6)	−0.0063 (5)	0.0027 (5)	−0.0077 (5)
C14	0.0806 (10)	0.0491 (8)	0.0576 (9)	0.0180 (7)	0.0223 (8)	0.0147 (7)
C15	0.0681 (10)	0.0977 (14)	0.0828 (12)	0.0204 (10)	−0.0036 (9)	0.0036 (11)
C16	0.0490 (7)	0.0647 (9)	0.0534 (8)	0.0063 (6)	−0.0028 (6)	0.0061 (7)
C17	0.0731 (10)	0.0509 (9)	0.0823 (11)	0.0074 (7)	−0.0021 (8)	0.0104 (8)
C18	0.0384 (6)	0.0414 (6)	0.0404 (6)	−0.0009 (5)	0.0078 (5)	−0.0056 (5)
C19	0.0549 (7)	0.0443 (7)	0.0369 (6)	−0.0011 (6)	0.0081 (5)	0.0005 (5)
C20	0.0579 (8)	0.0530 (8)	0.0338 (6)	−0.0018 (6)	0.0009 (5)	−0.0055 (5)
C21	0.0444 (6)	0.0408 (7)	0.0447 (7)	−0.0008 (5)	0.0057 (5)	−0.0096 (5)
C22	0.0494 (7)	0.0398 (7)	0.0467 (7)	0.0027 (5)	0.0043 (5)	0.0024 (5)
C23	0.0440 (6)	0.0467 (7)	0.0404 (6)	0.0017 (5)	−0.0026 (5)	0.0000 (5)
C24	0.0739 (10)	0.0446 (8)	0.0899 (12)	−0.0133 (7)	0.0053 (9)	−0.0044 (8)

O1—C21	1.3704 (15)	C12—H12	0.9300
O1—C24	1.4130 (18)	C13—C16	1.5011 (19)
N1—C1	1.3723 (15)	C14—C15	1.508 (2)
N1—C18	1.4131 (16)	C14—H14A	0.9700
N1—H1	0.902 (14)	C14—H14B	0.9700
N2—C7	1.2730 (15)	C15—H15A	0.9600
N2—C8	1.4265 (15)	C15—H15B	0.9600
C1—C6	1.4045 (16)	C15—H15C	0.9600
C1—C2	1.4147 (16)	C16—C17	1.519 (2)
C2—C3	1.3959 (16)	C16—H16A	0.9700
C2—C7	1.4545 (16)	C16—H16B	0.9700
C3—C4	1.3765 (17)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.3824 (19)	C17—H17C	0.9600
C4—H4	0.9300	C18—C23	1.3809 (18)
C5—C6	1.3731 (18)	C18—C19	1.3898 (18)
C5—H5	0.9300	C19—C20	1.3758 (18)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.3833 (19)
C8—C9	1.3955 (17)	C20—H20	0.9300
C8—C13	1.4019 (17)	C21—C22	1.3846 (19)
C9—C10	1.3932 (18)	C22—C23	1.3824 (18)
C9—C14	1.507 (2)	C22—H22	0.9300
C10—C11	1.375 (2)	C23—H23	0.9300
C10—H10	0.9300	C24—H24A	0.9600
C11—C12	1.374 (2)	C24—H24B	0.9600
C11—H11	0.9300	C24—H24C	0.9600
C12—C13	1.3925 (18)
C21—O1—C24	117.94 (11)	C15—C14—H14A	109.1
C1—N1—C18	125.73 (10)	C9—C14—H14B	109.1
C1—N1—H1	115.0 (9)	C15—C14—H14B	109.1
C18—N1—H1	119.1 (9)	H14A—C14—H14B	107.8
C7—N2—C8	118.26 (10)	C14—C15—H15A	109.5
N1—C1—C6	122.17 (11)	C14—C15—H15B	109.5
N1—C1—C2	119.91 (10)	H15A—C15—H15B	109.5
C6—C1—C2	117.90 (10)	C14—C15—H15C	109.5
C3—C2—C1	119.07 (10)	H15A—C15—H15C	109.5
C3—C2—C7	117.53 (11)	H15B—C15—H15C	109.5
C1—C2—C7	123.38 (10)	C13—C16—C17	112.94 (12)
C4—C3—C2	122.20 (12)	C13—C16—H16A	109.0
C4—C3—H3	118.9	C17—C16—H16A	109.0
C2—C3—H3	118.9	C13—C16—H16B	109.0
C3—C4—C5	118.36 (12)	C17—C16—H16B	109.0
C3—C4—H4	120.8	H16A—C16—H16B	107.8
C5—C4—H4	120.8	C16—C17—H17A	109.5
C6—C5—C4	121.32 (11)	C16—C17—H17B	109.5
C6—C5—H5	119.3	H17A—C17—H17B	109.5
C4—C5—H5	119.3	C16—C17—H17C	109.5
C5—C6—C1	121.12 (12)	H17A—C17—H17C	109.5
C5—C6—H6	119.4	H17B—C17—H17C	109.5
C1—C6—H6	119.4	C23—C18—C19	118.18 (11)
N2—C7—C2	124.84 (11)	C23—C18—N1	122.41 (11)
N2—C7—H7	117.6	C19—C18—N1	119.40 (11)
C2—C7—H7	117.6	C20—C19—C18	120.62 (12)
C9—C8—C13	121.95 (11)	C20—C19—H19	119.7
C9—C8—N2	119.61 (11)	C18—C19—H19	119.7
C13—C8—N2	118.34 (11)	C19—C20—C21	120.54 (12)
C10—C9—C8	117.96 (12)	C19—C20—H20	119.7
C10—C9—C14	120.89 (12)	C21—C20—H20	119.7
C8—C9—C14	121.10 (11)	O1—C21—C20	115.93 (11)
C11—C10—C9	121.01 (13)	O1—C21—C22	124.53 (12)
C11—C10—H10	119.5	C20—C21—C22	119.54 (12)
C9—C10—H10	119.5	C23—C22—C21	119.29 (12)
C12—C11—C10	120.16 (12)	C23—C22—H22	120.4
C12—C11—H11	119.9	C21—C22—H22	120.4
C10—C11—H11	119.9	C18—C23—C22	121.73 (12)
C11—C12—C13	121.45 (13)	C18—C23—H23	119.1
C11—C12—H12	119.3	C22—C23—H23	119.1
C13—C12—H12	119.3	O1—C24—H24A	109.5
C12—C13—C8	117.43 (13)	O1—C24—H24B	109.5
C12—C13—C16	121.32 (12)	H24A—C24—H24B	109.5
C8—C13—C16	121.18 (11)	O1—C24—H24C	109.5
C9—C14—C15	112.50 (13)	H24A—C24—H24C	109.5
C9—C14—H14A	109.1	H24B—C24—H24C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2	0.902 (14)	1.976 (15)	2.7126 (15)	137.8 (12)
C5—H5···Cg2i	0.93	2.79	3.5296 (8)	137
C10—H10···Cg1ii	0.93	2.84	3.7651 (6)	176
C16—H16A···Cg3iii	0.97	2.82	3.6614 (7)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2	0.902 (14)	1.976 (15)	2.7126 (15)	137.8 (12)
C5—H5⋯Cg2i	0.93	2.79	3.5296 (8)	137
C10—H10⋯Cg1ii	0.93	2.84	3.7651 (6)	176
C16—H16A⋯Cg3iii	0.97	2.82	3.6614 (7)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids the C8–C13, C18–C23 and C1–C6 rings, respectively.