2-[(2,6-Diethyl­phen­yl)imino­meth­yl]-N-(2-methoxy­phen­yl)aniline

Su, Q.; Wu, Q.-L.; Ye, L.; Mu, Y.

doi:10.1107/S1600536809037969

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2537

doi:10.1107/S1600536809037969

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2-[(2,6-Diethylphenyl)iminomethyl]-N-(2-methoxyphenyl)aniline

Qing Su,^a ^* Qiao-Lin Wu,^a Ling Ye ^b and Ying Mu ^b ^*

^aSchool of Chemistry, Jilin University, Changchun 130012, People's Republic of China, and ^bState Key Laboratory of Supramolecular Structure and Materials, School of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: suqing@jlu.edu.cn, ymu@jlu.edu.cn

(Received 4 August 2009; accepted 19 September 2009; online 26 September 2009)

The title anilide–imine compound, C₂₄H₂₆N₂O, features an intramolecular N—H⋯N hydrogen bond involving the imine and anilide groups to generate an S(6) ring motif. The molecule 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 interactions.

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 hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₆N₂O
M_r = 358.47
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.06
4670 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[-x+1, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y-1, -z; (iii) $[-x, y+{\script{5\over 2}}, -z+{\script{1\over 2}}]$ . Cg1, Cg2 and Cg3 are the centroids the C8–C13, C18–C23 and C1–C6 rings, respectively.

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.

Supporting information

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

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

checkCIF report

Comment top

A chelating anilide-imine compound has recently attracted increasing attention because it has a similar framwork and combination of steric and electronic characterics found in β-diketiminate and salicyaldiminato ligands which have been extensively researched in coordination chemistry and catalysis. (Wang et al., 2006) We have recently reported the luminescent properties of a series of zinc(II) (Su et al., 2007), aluminium(III) (Liu et al., 2005; 2006) and boron(III) (Ren et al., 2007) complexes with chelating anilido-imine ligands and catalytical properties of aluminium(III) (Yao et al., 2008) for the polymerization of ε-caprolactone. Good results have been obtained. As a part of our study, the preparation and crystal structure of the new anilido-imine title compound (I) (Fig. 1), is reported.

The bond lengths and angles are within normal ranges. The C7=N2 [1.2730 (15) Å] bond length is comparable to those found in similar anilido-imine compounds, such as {2-[(2,6-diethyl-phenylimino)-methyl]-phenyl}- (2,4-dimethyl-quinolin-7-yl)-amine [1.267 (4), 1.275 (4) Å] (Su et al., 2007) and {2-[(2,6-methyl-phenylimino)-methyl]-phenyl}- (2,4-dimethyl-quinolin-7-yl)-amine [1.271 (2) Å] (Su et al., 2007). The molecule adopts an E configuration about the central C=N bond. The dihedral angles between the central benzene ring (C1—C6) and the two outer benzene rings of the anilido-imine compound are 86.5° (C8—C13) and 54.2° (C18—C23). The dihedral angle between the C8—C13 and C18—C23 phenyl rings is 113.4°. An intramolecular N1—H1···N2 hydrogen bond forms a six-membered ring, generating an S(6) motif (Bernstein et al., 1995).

In the packing of the crystal, there exists three different types of C—H···π interactions (Fig.2 and Table1). The C—H···π interactions involving H10 form chains (Fig.2a). The additional C—H···π interactions through H5 and H16a interlink these chains (Fig.2b, and Fig.2c).

Related literature top

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 hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Preligand (2,6-Diethyl-phenyl)-(2-fluoro-benzylidene)-amine [ortho-C₆H₄(CH=NC₆H₃Et₂-2,6)] was synthesized according to a literature method (Su et al., 2007). A solution of nBuLi (1.60 mol/L, 9.2 mmol) in n-hexane was added to a solution of 4-methoxy-phenylamine (1.14 g, 9.2 mmol) in THF (20 ml) at -78 °C. The mixture was allowed to warm to room temperature and stirred for additional 4 h. The resulting solution was transferred into a solution of ortho-C₆H₄(CH=NC₆H₃Et₂-2,6) (2.36 g, 9.2 mmol) in THF at 25 °C. After stirring for two days, the reaction was quenched with H₂O (20 ml). The organic phase was evaporated to dryness to give the crude product as a brown oil that was purified by column chromatography on silica gel with ethyl acetate/ petroleum ether (1:34 in volume) as eluent. The pure product as yellow crystals (1.72 g, 52%) suitable for data collection were obtained after concentrating the solution. Anal. Calcd. for C₂₄H₂₆N₂O (358.48): C 80.41, H 7.36, N 7.81; Found: C 80.26, H 7.25, N 7.90%. ¹H NMR (500 MHz, CDCl₃, 298 K) δ (p.p.m.): 1.20 (t, 2 x 3H, J = 7.5 Hz, CH₃CH₂), 2.60 (q, 2 x 2H, J = 7.5 Hz, CH₃CH₂), 3.86 (s, 3H, O—CH₃), 6.80 (t, 1H, J = 6.5 Hz), 6.95 (d, 2H, J = 7.5 Hz), 7.10 (d, 1H, J = 6.0 Hz), 7.16 (br, 2H), 7.20 (d, 1H, J = 9.0 Hz), 7.28 (d, 3H, J = 3.5 Hz), 7.37 (d, 1H, J = 7.0 Hz), 8.76 (s, 1H, CH=N), 10.99 (br, 1H, NH).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates an intramolecular hydrogen bond.

Fig. 2. Packing of the molecule of (I) showing the different C—H···π interactions. Cg1: the centroid of the benzene ring (C8—C13); Cg2: the centroid of the benzene ring (C18—C23); Cg3: the centroid of the benzene ring (C1—C6). C10···Cg1 = 3.7651 (6) Å, C5···Cg2 = 3.5296 (8) Å, and C16···Cg3 = 3.6614 (7) Å. Only the hydrogen atoms involved in supramolecular interactions are shown for clarity. The green dots are the centers of the aromatic rings.

2-[(2,6-Diethylphenyl)iminomethyl]-N-(2-methoxyphenyl)aniline top

Crystal data top

C₂₄H₂₆N₂O	F(000) = 768
M_r = 358.47	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0487P)² + 0.2475P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4670 reflections	Δρ_max = 0.19 e Å⁻³
252 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₆N₂O	V = 2039.7 (7) Å³
M_r = 358.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.930 (3) Å	µ = 0.07 mm⁻¹
b = 7.4757 (15) Å	T = 295 K
c = 21.303 (4) Å	0.44 × 0.40 × 0.19 mm
β = 97.88 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4670 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3515 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.986	R_int = 0.035
19406 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.19 e Å⁻³
4670 reflections	Δρ_min = −0.17 e Å⁻³
252 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+3/2, −z+1/2; (ii) −x, −y−1, −z; (iii) −x, y+5/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₂O
M_r	358.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.930 (3), 7.4757 (15), 21.303 (4)
β (°)	97.88 (3)
V (Å³)	2039.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.44 × 0.40 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.969, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	19406, 4670, 3515
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.06
No. of reflections	4670
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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	2.793	3.5296 (8)	136.856
C10—H10···Cg1ⁱⁱ	0.93	2.837	3.7651 (6)	175.652
C16—H16A···Cg3ⁱⁱⁱ	0.97	2.816	3.6614 (7)	146.117

Symmetry codes: (i) −x+1, y+3/2, −z+1/2; (ii) −x, −y−1, −z; (iii) −x, y+5/2, −z+1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant Nos. 20772044 and 20674024). One of the authors (QS) is grateful for support from Jilin University.

References

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