2-Benzyl-6-(benzyl­amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Zhang, Y.; Han, G.-M.; Wu, Q.; Wang, H.-S.

doi:10.1107/S1600536807049975

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2-Benzyl-6-(benzylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Y. Zhang, G.-M. Han, Q. Wu and H.-S. Wang

The title compound, C₂₆H₂₀N₂O₂, is a 1,8-naphthalimide derivative. Molecules are arranged into stacks via π–π interactions between the naphthalimide systems, with interplanar distances of 3.379 (2) and 3.630 (2) Å. In addition, the crystal structure is stabilized by weak intermolecular C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049975/gk2103sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049975/gk2103Isup2.hkl Contains datablock I

CCDC reference: 636030

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
R factor = 0.051
wR factor = 0.136
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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No errors found in this datablock

Comment top

Since that the naphthalimide derivatives have been used as important dyes (Konstantinova et al., 2000), fluorescent taps (Mitchell et al., 1998) and photochemical DNA cleaving reagents (Xu et al., 2004), the synthesis of naphthalimides has attracted a great deal of attention. Here we report the synthesis and crystal structure of a new naphthalimide derivative.

The molecular structure of the title compound is shown in Fig.1. The molecular geometry is comparable with that of 2-benzyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (Sarma et al., 2007). The 1, 8-naphthalimide unit are almost planar.

Weak intermolecular C—H···O hydrogen bonds and π-π stacking interactions stabilize the crystal packing (Fig. 2).

Related literature top

For related literature, see: Konstantinova et al. (2000); Mitchell et al. (1998); Sarma et al. (2007); Xu et al. (2004).

Experimental top

The mixture of 4-bromo-1,8-naphthalic anhydride (0.28 g, 1 mmol), benzylamine (0.25 g, 2.3 mmol) and copper nitrate trihydrate (0.021 g, 0.1 mmol) was refluxed in ethylene glycol monomethyl ether (30 ml) for about 10 h, and cooled to afford the yellow powder of the title compound. Upon recrystallization from ethanol, yellow crystals were obtained (yield 46%, m.p. 428–430 K).

Structure description top

Weak intermolecular C—H···O hydrogen bonds and π-π stacking interactions stabilize the crystal packing (Fig. 2).

For related literature, see: Konstantinova et al. (2000); Mitchell et al. (1998); Sarma et al. (2007); Xu et al. (2004).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom labelling scheme. H atoms are represented by small spheres of arbitrary radius.
	Fig. 2. Packing diagram with H bonds indicated by dashed lines.

2-Benzyl-6-(benzylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione top

Crystal data top

C₂₆H₂₀N₂O₂	Z = 2
M_r = 392.44	F(000) = 412
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.354 (2) Å	Cell parameters from 1545 reflections
b = 10.314 (3) Å	θ = 2.5–26.6°
c = 12.503 (3) Å	µ = 0.08 mm⁻¹
α = 78.068 (4)°	T = 298 K
β = 87.225 (4)°	Prism, yellow
γ = 69.065 (4)°	0.27 × 0.23 × 0.14 mm
V = 984.1 (5) Å³

Data collection top

Rigaku Mercury diffractometer	3602 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (Jacobson, 1998)	h = −6→10
T_min = 0.978, T_max = 0.988	k = −11→12
5185 measured reflections	l = −14→15

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0683P)² + 0.0186P] where P = (F_o² + 2F_c²)/3
3602 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₆H₂₀N₂O₂	γ = 69.065 (4)°
M_r = 392.44	V = 984.1 (5) Å³
Triclinic, P1	Z = 2
a = 8.354 (2) Å	Mo Kα radiation
b = 10.314 (3) Å	µ = 0.08 mm⁻¹
c = 12.503 (3) Å	T = 298 K
α = 78.068 (4)°	0.27 × 0.23 × 0.14 mm
β = 87.225 (4)°

Data collection top

Rigaku Mercury diffractometer	3602 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2545 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.988	R_int = 0.017
5185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
3602 reflections	Δρ_min = −0.15 e Å⁻³
271 parameters

Special details top

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
C1	0.2622 (2)	0.59547 (19)	0.71932 (14)	0.0512 (5)
C2	0.2342 (2)	0.49746 (18)	0.81289 (13)	0.0477 (4)
C3	0.1932 (2)	0.3848 (2)	0.79810 (14)	0.0578 (5)
H3	0.1755	0.3763	0.7274	0.069*
C4	0.1775 (3)	0.2837 (2)	0.88512 (14)	0.0594 (5)
H4	0.1497	0.2087	0.8718	0.071*
C5	0.2025 (2)	0.29171 (18)	0.99235 (13)	0.0491 (4)
C6	0.2351 (2)	0.41232 (17)	1.01200 (13)	0.0444 (4)
C7	0.2521 (2)	0.43494 (19)	1.11711 (13)	0.0517 (5)
H7	0.2387	0.3706	1.1778	0.062*
C8	0.2876 (3)	0.54894 (19)	1.13225 (14)	0.0591 (5)
H8	0.2980	0.5618	1.2027	0.071*
C9	0.3086 (2)	0.64652 (19)	1.04242 (15)	0.0568 (5)
H9	0.3353	0.7231	1.0533	0.068*
C10	0.2900 (2)	0.63026 (17)	0.93806 (13)	0.0470 (4)
C11	0.2517 (2)	0.51367 (17)	0.92052 (13)	0.0433 (4)
C12	0.3131 (2)	0.73448 (19)	0.84477 (15)	0.0525 (5)
C13	0.3202 (2)	0.81558 (18)	0.64637 (14)	0.0573 (5)
H13A	0.2690	0.9099	0.6620	0.069*
H13B	0.2606	0.8130	0.5826	0.069*
C14	0.5053 (2)	0.78830 (18)	0.62048 (13)	0.0507 (5)
C15	0.5796 (3)	0.8849 (2)	0.63119 (16)	0.0697 (6)
H15	0.5142	0.9672	0.6550	0.084*
C16	0.7474 (4)	0.8621 (3)	0.60742 (19)	0.0871 (8)
H16	0.7951	0.9286	0.6149	0.105*
C17	0.8459 (3)	0.7410 (3)	0.57247 (18)	0.0887 (8)
H17	0.9607	0.7247	0.5570	0.106*
C18	0.7732 (3)	0.6437 (3)	0.56048 (18)	0.0822 (7)
H18	0.8387	0.5617	0.5363	0.099*
C19	0.6045 (3)	0.6681 (2)	0.58416 (16)	0.0643 (5)
H19	0.5562	0.6023	0.5756	0.077*
C20	0.1766 (3)	0.0588 (2)	1.06164 (15)	0.0712 (6)
H20A	0.2599	0.0172	1.0101	0.085*
H20B	0.0630	0.0818	1.0309	0.085*
C21	0.2003 (3)	−0.04668 (19)	1.16736 (14)	0.0555 (5)
C22	0.0616 (3)	−0.0690 (2)	1.22008 (15)	0.0632 (5)
H22	−0.0481	−0.0169	1.1904	0.076*
C23	0.0825 (3)	−0.1670 (2)	1.31597 (17)	0.0731 (6)
H23	−0.0128	−0.1805	1.3509	0.088*
C24	0.2425 (4)	−0.2446 (2)	1.36027 (17)	0.0772 (7)
H24	0.2564	−0.3111	1.4252	0.093*
C25	0.3827 (3)	−0.2244 (2)	1.30889 (18)	0.0779 (7)
H25	0.4920	−0.2773	1.3389	0.093*
C26	0.3621 (3)	−0.1256 (2)	1.21254 (16)	0.0684 (6)
H26	0.4577	−0.1122	1.1779	0.082*
N1	0.29555 (19)	0.71192 (14)	0.74032 (11)	0.0503 (4)
N2	0.1971 (2)	0.18745 (15)	1.07740 (11)	0.0610 (5)
H2	0.2061	0.1982	1.1430	0.073*
O1	0.34627 (19)	0.83731 (13)	0.85503 (10)	0.0699 (4)
O2	0.25983 (18)	0.58088 (14)	0.62488 (9)	0.0659 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (11)	0.0597 (11)	0.0461 (10)	−0.0226 (9)	−0.0022 (8)	−0.0061 (8)
C2	0.0472 (11)	0.0534 (10)	0.0436 (9)	−0.0210 (9)	−0.0011 (8)	−0.0061 (8)
C3	0.0690 (14)	0.0725 (12)	0.0411 (10)	−0.0367 (11)	−0.0038 (9)	−0.0097 (9)
C4	0.0766 (14)	0.0662 (12)	0.0499 (11)	−0.0426 (11)	−0.0026 (9)	−0.0107 (9)
C5	0.0501 (11)	0.0532 (10)	0.0458 (10)	−0.0223 (9)	−0.0007 (8)	−0.0061 (8)
C6	0.0402 (10)	0.0487 (9)	0.0432 (9)	−0.0145 (8)	0.0012 (7)	−0.0095 (7)
C7	0.0569 (12)	0.0553 (10)	0.0413 (10)	−0.0190 (10)	0.0049 (8)	−0.0090 (8)
C8	0.0768 (14)	0.0615 (11)	0.0433 (10)	−0.0257 (11)	0.0048 (9)	−0.0188 (9)
C9	0.0698 (14)	0.0476 (10)	0.0556 (11)	−0.0185 (10)	0.0049 (9)	−0.0207 (9)
C10	0.0469 (11)	0.0445 (9)	0.0463 (10)	−0.0115 (8)	0.0029 (8)	−0.0111 (8)
C11	0.0368 (10)	0.0458 (9)	0.0452 (9)	−0.0122 (8)	0.0010 (7)	−0.0087 (7)
C12	0.0526 (12)	0.0448 (10)	0.0555 (11)	−0.0117 (9)	0.0039 (9)	−0.0107 (8)
C13	0.0657 (13)	0.0480 (10)	0.0511 (11)	−0.0179 (10)	0.0007 (9)	0.0015 (8)
C14	0.0622 (13)	0.0512 (10)	0.0387 (9)	−0.0243 (10)	−0.0013 (8)	−0.0010 (8)
C15	0.0874 (17)	0.0710 (13)	0.0614 (13)	−0.0424 (13)	0.0019 (11)	−0.0108 (10)
C16	0.095 (2)	0.120 (2)	0.0694 (15)	−0.0721 (19)	0.0012 (13)	−0.0072 (14)
C17	0.0613 (16)	0.143 (3)	0.0605 (14)	−0.0467 (18)	0.0057 (11)	0.0000 (15)
C18	0.0653 (16)	0.0978 (18)	0.0756 (15)	−0.0195 (15)	0.0112 (12)	−0.0200 (13)
C19	0.0647 (14)	0.0652 (12)	0.0647 (12)	−0.0246 (11)	0.0037 (10)	−0.0145 (10)
C20	0.1121 (19)	0.0646 (12)	0.0507 (11)	−0.0492 (13)	0.0010 (11)	−0.0089 (9)
C21	0.0787 (15)	0.0487 (10)	0.0465 (10)	−0.0296 (11)	0.0021 (10)	−0.0134 (8)
C22	0.0721 (15)	0.0583 (12)	0.0602 (12)	−0.0228 (11)	0.0038 (10)	−0.0151 (10)
C23	0.0967 (19)	0.0731 (14)	0.0591 (13)	−0.0431 (14)	0.0204 (12)	−0.0151 (11)
C24	0.128 (2)	0.0574 (13)	0.0464 (11)	−0.0338 (15)	0.0044 (14)	−0.0089 (9)
C25	0.0922 (18)	0.0687 (14)	0.0629 (13)	−0.0132 (13)	−0.0133 (13)	−0.0161 (11)
C26	0.0743 (15)	0.0782 (14)	0.0596 (12)	−0.0333 (13)	0.0089 (11)	−0.0194 (11)
N1	0.0542 (10)	0.0476 (8)	0.0455 (8)	−0.0172 (8)	0.0004 (7)	−0.0029 (6)
N2	0.0911 (13)	0.0584 (9)	0.0430 (8)	−0.0393 (9)	0.0003 (8)	−0.0078 (7)
O1	0.0988 (12)	0.0489 (7)	0.0684 (9)	−0.0333 (8)	0.0052 (8)	−0.0136 (6)
O2	0.0870 (11)	0.0811 (9)	0.0396 (7)	−0.0448 (9)	−0.0036 (6)	−0.0057 (6)

Geometric parameters (Å, º) top

C1—O2	1.223 (2)	C14—C19	1.376 (3)
C1—N1	1.402 (2)	C14—C15	1.379 (2)
C1—C2	1.449 (2)	C15—C16	1.364 (3)
C2—C3	1.371 (2)	C15—H15	0.9300
C2—C11	1.411 (2)	C16—C17	1.372 (3)
C3—C4	1.380 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.380 (3)
C4—C5	1.390 (2)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.369 (3)
C5—N2	1.359 (2)	C18—H18	0.9300
C5—C6	1.434 (2)	C19—H19	0.9300
C6—C7	1.404 (2)	C20—N2	1.450 (2)
C6—C11	1.419 (2)	C20—C21	1.499 (2)
C7—C8	1.361 (2)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—C9	1.394 (2)	C21—C22	1.372 (3)
C8—H8	0.9300	C21—C26	1.381 (3)
C9—C10	1.372 (2)	C22—C23	1.372 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.410 (2)	C23—C24	1.363 (3)
C10—C12	1.470 (2)	C23—H23	0.9300
C12—O1	1.219 (2)	C24—C25	1.369 (3)
C12—N1	1.396 (2)	C24—H24	0.9300
C13—N1	1.4765 (19)	C25—C26	1.381 (3)
C13—C14	1.501 (3)	C25—H25	0.9300
C13—H13A	0.9700	C26—H26	0.9300
C13—H13B	0.9700	N2—H2	0.8600

O2—C1—N1	119.24 (15)	C16—C15—C14	121.2 (2)
O2—C1—C2	123.69 (17)	C16—C15—H15	119.4
N1—C1—C2	117.07 (15)	C14—C15—H15	119.4
C3—C2—C11	118.65 (15)	C15—C16—C17	120.2 (2)
C3—C2—C1	120.19 (16)	C15—C16—H16	119.9
C11—C2—C1	121.14 (16)	C17—C16—H16	119.9
C2—C3—C4	121.88 (16)	C16—C17—C18	119.4 (2)
C2—C3—H3	119.1	C16—C17—H17	120.3
C4—C3—H3	119.1	C18—C17—H17	120.3
C3—C4—C5	121.24 (17)	C19—C18—C17	119.9 (2)
C3—C4—H4	119.4	C19—C18—H18	120.0
C5—C4—H4	119.4	C17—C18—H18	120.0
N2—C5—C4	121.01 (16)	C18—C19—C14	121.1 (2)
N2—C5—C6	120.23 (15)	C18—C19—H19	119.5
C4—C5—C6	118.76 (15)	C14—C19—H19	119.5
C7—C6—C11	118.34 (16)	N2—C20—C21	111.32 (15)
C7—C6—C5	123.34 (16)	N2—C20—H20A	109.4
C11—C6—C5	118.32 (15)	C21—C20—H20A	109.4
C8—C7—C6	121.49 (16)	N2—C20—H20B	109.4
C8—C7—H7	119.3	C21—C20—H20B	109.4
C6—C7—H7	119.3	H20A—C20—H20B	108.0
C7—C8—C9	120.20 (17)	C22—C21—C26	118.61 (18)
C7—C8—H8	119.9	C22—C21—C20	120.6 (2)
C9—C8—H8	119.9	C26—C21—C20	120.8 (2)
C10—C9—C8	120.39 (17)	C23—C22—C21	120.9 (2)
C10—C9—H9	119.8	C23—C22—H22	119.5
C8—C9—H9	119.8	C21—C22—H22	119.5
C9—C10—C11	120.33 (16)	C24—C23—C22	120.2 (2)
C9—C10—C12	119.31 (16)	C24—C23—H23	119.9
C11—C10—C12	120.35 (16)	C22—C23—H23	119.9
C10—C11—C2	119.83 (15)	C23—C24—C25	119.8 (2)
C10—C11—C6	119.21 (15)	C23—C24—H24	120.1
C2—C11—C6	120.94 (16)	C25—C24—H24	120.1
O1—C12—N1	119.74 (16)	C24—C25—C26	120.1 (2)
O1—C12—C10	123.19 (17)	C24—C25—H25	119.9
N1—C12—C10	117.07 (16)	C26—C25—H25	119.9
N1—C13—C14	113.22 (14)	C25—C26—C21	120.3 (2)
N1—C13—H13A	108.9	C25—C26—H26	119.8
C14—C13—H13A	108.9	C21—C26—H26	119.8
N1—C13—H13B	108.9	C12—N1—C1	124.40 (14)
C14—C13—H13B	108.9	C12—N1—C13	117.28 (14)
H13A—C13—H13B	107.7	C1—N1—C13	118.28 (14)
C19—C14—C15	118.26 (19)	C5—N2—C20	122.42 (15)
C19—C14—C13	121.24 (17)	C5—N2—H2	118.8
C15—C14—C13	120.49 (18)	C20—N2—H2	118.8

O2—C1—C2—C3	−3.7 (3)	C11—C10—C12—N1	−0.1 (3)
N1—C1—C2—C3	177.04 (15)	N1—C13—C14—C19	65.5 (2)
O2—C1—C2—C11	174.97 (17)	N1—C13—C14—C15	−115.45 (18)
N1—C1—C2—C11	−4.3 (3)	C19—C14—C15—C16	−0.5 (3)
C11—C2—C3—C4	−3.4 (3)	C13—C14—C15—C16	−179.64 (18)
C1—C2—C3—C4	175.33 (18)	C14—C15—C16—C17	−0.2 (3)
C2—C3—C4—C5	0.1 (3)	C15—C16—C17—C18	0.7 (3)
C3—C4—C5—N2	−176.01 (18)	C16—C17—C18—C19	−0.5 (3)
C3—C4—C5—C6	3.7 (3)	C17—C18—C19—C14	−0.3 (3)
N2—C5—C6—C7	−4.1 (3)	C15—C14—C19—C18	0.8 (3)
C4—C5—C6—C7	176.14 (17)	C13—C14—C19—C18	179.89 (18)
N2—C5—C6—C11	175.62 (16)	N2—C20—C21—C22	104.6 (2)
C4—C5—C6—C11	−4.1 (3)	N2—C20—C21—C26	−76.8 (2)
C11—C6—C7—C8	−1.6 (3)	C26—C21—C22—C23	0.3 (3)
C5—C6—C7—C8	178.19 (17)	C20—C21—C22—C23	178.92 (17)
C6—C7—C8—C9	−0.2 (3)	C21—C22—C23—C24	−0.3 (3)
C7—C8—C9—C10	1.4 (3)	C22—C23—C24—C25	0.1 (3)
C8—C9—C10—C11	−0.8 (3)	C23—C24—C25—C26	0.1 (3)
C8—C9—C10—C12	−179.88 (17)	C24—C25—C26—C21	0.0 (3)
C9—C10—C11—C2	−179.52 (16)	C22—C21—C26—C25	−0.2 (3)
C12—C10—C11—C2	−0.5 (3)	C20—C21—C26—C25	−178.77 (18)
C9—C10—C11—C6	−1.0 (3)	O1—C12—N1—C1	178.24 (17)
C12—C10—C11—C6	178.12 (16)	C10—C12—N1—C1	−1.8 (3)
C3—C2—C11—C10	−178.62 (16)	O1—C12—N1—C13	0.6 (2)
C1—C2—C11—C10	2.7 (3)	C10—C12—N1—C13	−179.45 (15)
C3—C2—C11—C6	2.8 (3)	O2—C1—N1—C12	−175.40 (16)
C1—C2—C11—C6	−175.87 (16)	C2—C1—N1—C12	3.9 (3)
C7—C6—C11—C10	2.1 (3)	O2—C1—N1—C13	2.3 (2)
C5—C6—C11—C10	−177.67 (15)	C2—C1—N1—C13	−178.47 (15)
C7—C6—C11—C2	−179.35 (15)	C14—C13—N1—C12	82.09 (19)
C5—C6—C11—C2	0.9 (3)	C14—C13—N1—C1	−95.74 (19)
C9—C10—C12—O1	−1.0 (3)	C4—C5—N2—C20	4.1 (3)
C11—C10—C12—O1	179.94 (16)	C6—C5—N2—C20	−175.57 (18)
C9—C10—C12—N1	179.02 (16)	C21—C20—N2—C5	171.73 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2	0.97	2.35	2.709 (2)	101
C17—H17···O2ⁱ	0.93	2.49	3.287 (3)	144
C19—H19···O2	0.93	2.60	3.298 (3)	133
C22—H22···O1ⁱⁱ	0.93	2.52	3.430 (3)	165
C24—H24···O2ⁱⁱⁱ	0.93	2.51	3.407 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₂
M_r	392.44
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.354 (2), 10.314 (3), 12.503 (3)
α, β, γ (°)	78.068 (4), 87.225 (4), 69.065 (4)
V (Å³)	984.1 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.23 × 0.14

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.978, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5185, 3602, 2545
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.136, 1.04
No. of reflections	3602
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2	0.97	2.35	2.709 (2)	101
C17—H17···O2ⁱ	0.93	2.49	3.287 (3)	144
C19—H19···O2	0.93	2.60	3.298 (3)	133
C22—H22···O1ⁱⁱ	0.93	2.52	3.430 (3)	165
C24—H24···O2ⁱⁱⁱ	0.93	2.51	3.407 (3)	162

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

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