(E)-3-[4-(Diphenyl­amino)­phen­yl]-1-(pyridin-2-yl)prop-2-en-1-one

Fan, C.-B.; Wang, X.-M.

doi:10.1107/S1600536811055036

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o417

doi:10.1107/S1600536811055036

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(E)-3-[4-(Diphenylamino)phenyl]-1-(pyridin-2-yl)prop-2-en-1-one

Cong-Bin Fan ^a and Xiao-Mei Wang ^a,^b ^*

^aCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China, and ^bJiangsu Key Laboratory for Environment Functional Materials, Suzhou University of Science and Technology, Suzhou 215009, People's Republic of China
^*Correspondence e-mail: wangxiaomeisuda@126.com

(Received 16 December 2011; accepted 21 December 2011; online 14 January 2012)

The title compound, C₂₆H₂₀N₂O, belongs to a new family of organic two-photon absorption materials with triphenylamine and pyridine units. In the molecule, the three benzene rings are arranged in a propeller-like fashion; the dihedral angles between the rings are 80.01 (14), 75.68 (13) and 56.93 (14)°. The pyridine ring is oriented at dihedral angles of 56.24 (14), 48.92 (15) and 22.02 (13)° with respect to the three benzene rings. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of two-photon absorption compounds, see: Fan et al. (2012 ); He et al. (2008 ).

Experimental

Crystal data

C₂₆H₂₀N₂O
M_r = 376.44
Monoclinic, P 2₁ /c
a = 12.0342 (3) Å
b = 17.4069 (4) Å
c = 9.4392 (2) Å
β = 91.757 (2)°
V = 1976.38 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
15074 measured reflections
3488 independent reflections
2210 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.167
S = 1.03
3488 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.55	3.404 (3)	153
C6—H6⋯O1ⁱⁱ	0.93	2.58	3.505 (3)	179
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055036/xu5410sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055036/xu5410Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055036/xu5410Isup3.cml

checkCIF report

Comment top

Organic materials with two-photon absorption (TPA) properties have attracted increasing attention due to their versatile potential applications in two-photon excited fluorescence (Fan et al., 2012), three-dimensional microfabrication, high-density optical data storage, optical limiting, stabilization and reshaping (He et al., 2008). However, the basic structure-function relationships regarding enhanced TPA properties remain unclear. To further understand this important issue, we synthesized the two-photon absorption material with triphenylamine and pyridine units. This compound when dissolved in tetrahydrofuran shows absorption peak 430 nm. It must be noted that there is no linear absorption for the title chromophores beyond 800 nm. The laser pumped wavelength is 850 nm which is matching with absorption peak 430 nm, the linear absorption can be excluded because two-photon excitation via virtual intermediate state can proceed, consistent with the fact that the nonlinear absorption occurs at a frequency in the region of one-photon transparency. The title chromophore shows two-photon absorption fluorescence spectra at 546 nm when excited with 850 nm femtosecond laser pulses.

Related literature top

For applications of two-photon absorption compounds, see: Fan et al. (2012); He et al. (2008).

Experimental top

To a 100 mL methanol solution of 4-(diphenylamino) benzaldehyde (1.37 g, 5.0 mmol) was added 2-acetylpridine (0.61 g, 5.0 mmol) and 2% aqueous NaOH (0.44 g, 22 mL). The mixture was stirred for 2 h at room temperature (Scheme 1). The yellow precipitate formed was collected by filtration, and washed sequentially with water and methanol for three times, respectively.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(E)-3-[4-(Diphenylamino)phenyl]-1-(pyridin-2-yl)prop-2-en-1-one top

Crystal data top

C₂₆H₂₀N₂O	F(000) = 792
M_r = 376.44	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 467 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.0342 (3) Å	Cell parameters from 2266 reflections
b = 17.4069 (4) Å	θ = 2.5–21.1°
c = 9.4392 (2) Å	µ = 0.08 mm⁻¹
β = 91.757 (2)°	T = 296 K
V = 1976.38 (8) Å³	Block, orange
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −14→14
15074 measured reflections	k = −17→20
3488 independent reflections	l = −11→11

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0774P)² + 0.1969P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3488 reflections	Δρ_max = 0.17 e Å⁻³
263 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (18)

Crystal data top

C₂₆H₂₀N₂O	V = 1976.38 (8) Å³
M_r = 376.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0342 (3) Å	µ = 0.08 mm⁻¹
b = 17.4069 (4) Å	T = 296 K
c = 9.4392 (2) Å	0.20 × 0.20 × 0.18 mm
β = 91.757 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2210 reflections with I > 2σ(I)
15074 measured reflections	R_int = 0.046
3488 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
3488 reflections	Δρ_min = −0.16 e Å⁻³
263 parameters

Special details top

Experimental. ¹H NMR (CDCl₃; 400 MHz; TMS): ppm: 7.00-7.03 (m, 2H, Ar-H), 7.09-7.18 (m, 6H, Ar-H), 7.26-7.36 (m, 7H, Ar-H, pyr-H), 7.46-7.49 (m, 1H, Ar-H), 7.57, 7.59 (d, 1H, -CH=), 7.67, 7.69 (d, 1H, -CH=), 7.87-7.92 (m, 1H, pyr-H), 8.13-8.20 (m, 1H, pyr-H), 8.72, 8.74 (d, 1H, pyr-H)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.37944 (18)	0.15352 (15)	0.1848 (2)	0.0604 (6)
C2	0.4306 (2)	0.22083 (15)	0.1472 (3)	0.0724 (7)
H2	0.4013	0.2498	0.0721	0.087*
C3	0.5246 (2)	0.24556 (18)	0.2199 (3)	0.0821 (8)
H3	0.5590	0.2911	0.1939	0.099*
C4	0.5675 (2)	0.2031 (2)	0.3304 (3)	0.0829 (9)
H4	0.6305	0.2204	0.3803	0.099*
C5	0.5181 (2)	0.13502 (18)	0.3686 (3)	0.0794 (8)
H5	0.5484	0.1059	0.4428	0.095*
C6	0.4231 (2)	0.11022 (15)	0.2955 (3)	0.0686 (7)
H6	0.3890	0.0646	0.3210	0.082*
C7	0.28491 (19)	0.11150 (14)	−0.0356 (2)	0.0592 (6)
C8	0.1950 (2)	0.12480 (17)	−0.1262 (3)	0.0757 (8)
H8	0.1298	0.1450	−0.0913	0.091*
C9	0.2017 (3)	0.1082 (2)	−0.2684 (3)	0.0987 (11)
H9	0.1402	0.1166	−0.3285	0.118*
C10	0.2972 (3)	0.0796 (2)	−0.3223 (3)	0.1014 (11)
H10	0.3008	0.0683	−0.4183	0.122*
C11	0.3868 (3)	0.06786 (17)	−0.2342 (3)	0.0889 (9)
H11	0.4526	0.0493	−0.2706	0.107*
C12	0.3814 (2)	0.08311 (15)	−0.0914 (3)	0.0728 (7)
H12	0.4432	0.0742	−0.0321	0.087*
C13	0.18324 (18)	0.11941 (14)	0.1885 (2)	0.0615 (6)
C14	0.1670 (2)	0.16653 (16)	0.3048 (3)	0.0728 (7)
H14	0.2185	0.2047	0.3277	0.087*
C15	0.0747 (2)	0.15704 (16)	0.3865 (3)	0.0735 (7)
H15	0.0651	0.1894	0.4636	0.088*
C16	0.10415 (18)	0.06364 (14)	0.1553 (2)	0.0630 (6)
H16	0.1133	0.0319	0.0773	0.076*
C17	0.01208 (19)	0.05508 (15)	0.2374 (3)	0.0662 (7)
H17	−0.0406	0.0180	0.2125	0.079*
C18	−0.00423 (19)	0.10043 (15)	0.3566 (3)	0.0634 (6)
C19	−0.0996 (2)	0.08741 (15)	0.4450 (3)	0.0703 (7)
H19	−0.1560	0.0565	0.4068	0.084*
C20	−0.1147 (2)	0.11495 (15)	0.5740 (3)	0.0700 (7)
H20	−0.0612	0.1476	0.6138	0.084*
C21	−0.2123 (2)	0.09591 (15)	0.6561 (3)	0.0652 (7)
C22	−0.21265 (18)	0.11975 (13)	0.8081 (3)	0.0593 (6)
C23	−0.2974 (2)	0.09692 (16)	0.8930 (3)	0.0709 (7)
H23	−0.3557	0.0674	0.8556	0.085*
C24	−0.2956 (2)	0.11791 (17)	1.0331 (3)	0.0776 (8)
H24	−0.3519	0.1023	1.0920	0.093*
C25	−0.2104 (2)	0.16171 (17)	1.0843 (3)	0.0808 (8)
H25	−0.2081	0.1782	1.1780	0.097*
C26	−0.1279 (2)	0.18110 (19)	0.9946 (4)	0.0951 (10)
H26	−0.0683	0.2096	1.0312	0.114*
N1	0.28066 (15)	0.12811 (12)	0.1108 (2)	0.0678 (6)
N2	−0.12745 (18)	0.16178 (14)	0.8578 (3)	0.0838 (7)
O1	−0.29203 (14)	0.06052 (12)	0.60544 (19)	0.0871 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0511 (12)	0.0775 (17)	0.0531 (13)	−0.0055 (12)	0.0112 (11)	−0.0105 (12)
C2	0.0659 (15)	0.0799 (19)	0.0721 (16)	−0.0092 (14)	0.0117 (13)	0.0002 (14)
C3	0.0770 (18)	0.088 (2)	0.082 (2)	−0.0209 (16)	0.0153 (16)	−0.0128 (16)
C4	0.0626 (16)	0.113 (2)	0.0733 (18)	−0.0179 (17)	0.0095 (14)	−0.0329 (18)
C5	0.0730 (17)	0.105 (2)	0.0602 (16)	0.0035 (17)	0.0014 (14)	−0.0096 (15)
C6	0.0686 (15)	0.0775 (17)	0.0601 (15)	−0.0093 (13)	0.0092 (13)	−0.0035 (13)
C7	0.0565 (13)	0.0688 (16)	0.0528 (13)	−0.0087 (11)	0.0108 (11)	−0.0030 (11)
C8	0.0592 (15)	0.102 (2)	0.0659 (17)	−0.0043 (14)	0.0051 (13)	0.0095 (15)
C9	0.083 (2)	0.149 (3)	0.0627 (18)	−0.030 (2)	−0.0072 (16)	0.0169 (18)
C10	0.104 (2)	0.141 (3)	0.0603 (17)	−0.049 (2)	0.0226 (18)	−0.0211 (18)
C11	0.085 (2)	0.102 (2)	0.082 (2)	−0.0166 (17)	0.0294 (17)	−0.0265 (17)
C12	0.0631 (15)	0.090 (2)	0.0660 (16)	0.0002 (13)	0.0146 (12)	−0.0121 (14)
C13	0.0496 (13)	0.0759 (17)	0.0596 (14)	−0.0029 (12)	0.0119 (11)	0.0001 (12)
C14	0.0644 (15)	0.0803 (19)	0.0751 (17)	−0.0125 (13)	0.0238 (13)	−0.0141 (14)
C15	0.0672 (16)	0.0824 (18)	0.0719 (16)	−0.0018 (14)	0.0205 (13)	−0.0113 (14)
C16	0.0568 (14)	0.0767 (17)	0.0559 (14)	−0.0016 (12)	0.0077 (11)	−0.0004 (12)
C17	0.0561 (13)	0.0777 (17)	0.0651 (15)	−0.0067 (12)	0.0088 (12)	0.0049 (13)
C18	0.0532 (13)	0.0729 (16)	0.0649 (15)	0.0024 (12)	0.0119 (11)	0.0076 (13)
C19	0.0601 (14)	0.0805 (18)	0.0710 (17)	0.0008 (13)	0.0165 (13)	0.0107 (13)
C20	0.0548 (14)	0.0858 (18)	0.0705 (16)	−0.0019 (12)	0.0173 (12)	0.0074 (14)
C21	0.0528 (14)	0.0754 (17)	0.0680 (16)	0.0014 (12)	0.0106 (12)	0.0091 (13)
C22	0.0477 (12)	0.0608 (15)	0.0699 (15)	0.0034 (11)	0.0119 (11)	0.0023 (12)
C23	0.0572 (14)	0.0858 (19)	0.0705 (16)	−0.0067 (13)	0.0139 (12)	−0.0055 (14)
C24	0.0697 (17)	0.090 (2)	0.0737 (18)	0.0008 (15)	0.0190 (14)	−0.0040 (15)
C25	0.0719 (17)	0.097 (2)	0.0740 (18)	0.0114 (16)	0.0064 (14)	−0.0146 (16)
C26	0.0718 (18)	0.113 (2)	0.101 (2)	−0.0186 (17)	0.0135 (17)	−0.0349 (19)
N1	0.0469 (11)	0.1011 (16)	0.0559 (12)	−0.0106 (10)	0.0117 (9)	−0.0101 (11)
N2	0.0690 (14)	0.0918 (17)	0.0919 (17)	−0.0185 (12)	0.0224 (12)	−0.0184 (14)
O1	0.0638 (11)	0.1250 (16)	0.0731 (12)	−0.0188 (11)	0.0105 (9)	−0.0031 (11)

Geometric parameters (Å, º) top

C1—C2	1.375 (3)	C13—N1	1.410 (3)
C1—C6	1.379 (3)	C14—C15	1.381 (3)
C1—N1	1.430 (3)	C14—H14	0.9300
C2—C3	1.374 (4)	C15—C18	1.392 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.366 (4)	C16—C17	1.380 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.379 (4)	C17—C18	1.394 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.386 (3)	C18—C19	1.457 (3)
C5—H5	0.9300	C19—C20	1.326 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.378 (3)	C20—C21	1.466 (3)
C7—C12	1.382 (3)	C20—H20	0.9300
C7—N1	1.414 (3)	C21—O1	1.225 (3)
C8—C9	1.377 (4)	C21—C22	1.493 (3)
C8—H8	0.9300	C22—N2	1.333 (3)
C9—C10	1.365 (4)	C22—C23	1.375 (3)
C9—H9	0.9300	C23—C24	1.372 (4)
C10—C11	1.357 (4)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.355 (4)
C11—C12	1.377 (4)	C24—H24	0.9300
C11—H11	0.9300	C25—C26	1.366 (4)
C12—H12	0.9300	C25—H25	0.9300
C13—C14	1.389 (3)	C26—N2	1.335 (3)
C13—C16	1.389 (3)	C26—H26	0.9300

C2—C1—C6	119.9 (2)	C13—C14—H14	119.8
C2—C1—N1	120.6 (2)	C14—C15—C18	121.8 (2)
C6—C1—N1	119.5 (2)	C14—C15—H15	119.1
C3—C2—C1	120.4 (3)	C18—C15—H15	119.1
C3—C2—H2	119.8	C17—C16—C13	120.4 (2)
C1—C2—H2	119.8	C17—C16—H16	119.8
C4—C3—C2	119.8 (3)	C13—C16—H16	119.8
C4—C3—H3	120.1	C16—C17—C18	121.9 (2)
C2—C3—H3	120.1	C16—C17—H17	119.1
C3—C4—C5	120.6 (3)	C18—C17—H17	119.1
C3—C4—H4	119.7	C15—C18—C17	116.9 (2)
C5—C4—H4	119.7	C15—C18—C19	122.6 (2)
C4—C5—C6	119.5 (3)	C17—C18—C19	120.5 (2)
C4—C5—H5	120.2	C20—C19—C18	127.0 (3)
C6—C5—H5	120.2	C20—C19—H19	116.5
C1—C6—C5	119.8 (3)	C18—C19—H19	116.5
C1—C6—H6	120.1	C19—C20—C21	122.6 (3)
C5—C6—H6	120.1	C19—C20—H20	118.7
C8—C7—C12	118.5 (2)	C21—C20—H20	118.7
C8—C7—N1	121.4 (2)	O1—C21—C20	122.5 (2)
C12—C7—N1	120.1 (2)	O1—C21—C22	119.3 (2)
C9—C8—C7	120.1 (3)	C20—C21—C22	118.1 (2)
C9—C8—H8	119.9	N2—C22—C23	122.0 (2)
C7—C8—H8	119.9	N2—C22—C21	117.8 (2)
C10—C9—C8	120.9 (3)	C23—C22—C21	120.2 (2)
C10—C9—H9	119.5	C24—C23—C22	119.6 (3)
C8—C9—H9	119.5	C24—C23—H23	120.2
C11—C10—C9	119.3 (3)	C22—C23—H23	120.2
C11—C10—H10	120.4	C25—C24—C23	118.9 (3)
C9—C10—H10	120.4	C25—C24—H24	120.6
C10—C11—C12	120.7 (3)	C23—C24—H24	120.6
C10—C11—H11	119.7	C24—C25—C26	118.3 (3)
C12—C11—H11	119.7	C24—C25—H25	120.8
C11—C12—C7	120.5 (3)	C26—C25—H25	120.8
C11—C12—H12	119.8	N2—C26—C25	124.2 (3)
C7—C12—H12	119.8	N2—C26—H26	117.9
C14—C13—C16	118.6 (2)	C25—C26—H26	117.9
C14—C13—N1	119.2 (2)	C13—N1—C7	122.81 (19)
C16—C13—N1	122.2 (2)	C13—N1—C1	118.08 (18)
C15—C14—C13	120.4 (2)	C7—N1—C1	119.09 (18)
C15—C14—H14	119.8	C22—N2—C26	116.9 (2)

C6—C1—C2—C3	−0.5 (4)	C18—C19—C20—C21	−177.7 (2)
N1—C1—C2—C3	179.1 (2)	C19—C20—C21—O1	−8.4 (4)
C1—C2—C3—C4	−0.1 (4)	C19—C20—C21—C22	170.5 (2)
C2—C3—C4—C5	0.9 (4)	O1—C21—C22—N2	−176.4 (2)
C3—C4—C5—C6	−1.1 (4)	C20—C21—C22—N2	4.6 (3)
C2—C1—C6—C5	0.3 (4)	O1—C21—C22—C23	5.1 (4)
N1—C1—C6—C5	−179.3 (2)	C20—C21—C22—C23	−173.8 (2)
C4—C5—C6—C1	0.5 (4)	N2—C22—C23—C24	0.3 (4)
C12—C7—C8—C9	1.5 (4)	C21—C22—C23—C24	178.7 (2)
N1—C7—C8—C9	179.8 (3)	C22—C23—C24—C25	0.8 (4)
C7—C8—C9—C10	−1.0 (5)	C23—C24—C25—C26	−2.0 (4)
C8—C9—C10—C11	−0.4 (5)	C24—C25—C26—N2	2.3 (5)
C9—C10—C11—C12	1.2 (5)	C14—C13—N1—C7	−150.5 (2)
C10—C11—C12—C7	−0.7 (4)	C16—C13—N1—C7	31.4 (4)
C8—C7—C12—C11	−0.6 (4)	C14—C13—N1—C1	30.6 (3)
N1—C7—C12—C11	−179.0 (2)	C16—C13—N1—C1	−147.4 (2)
C16—C13—C14—C15	1.0 (4)	C8—C7—N1—C13	34.6 (4)
N1—C13—C14—C15	−177.2 (2)	C12—C7—N1—C13	−147.1 (2)
C13—C14—C15—C18	0.4 (4)	C8—C7—N1—C1	−146.6 (2)
C14—C13—C16—C17	−0.6 (4)	C12—C7—N1—C1	31.7 (3)
N1—C13—C16—C17	177.5 (2)	C2—C1—N1—C13	−119.3 (3)
C13—C16—C17—C18	−1.1 (4)	C6—C1—N1—C13	60.2 (3)
C14—C15—C18—C17	−2.0 (4)	C2—C1—N1—C7	61.8 (3)
C14—C15—C18—C19	177.4 (2)	C6—C1—N1—C7	−118.6 (2)
C16—C17—C18—C15	2.4 (4)	C23—C22—N2—C26	−0.1 (4)
C16—C17—C18—C19	−177.0 (2)	C21—C22—N2—C26	−178.5 (2)
C15—C18—C19—C20	−13.4 (4)	C25—C26—N2—C22	−1.2 (5)
C17—C18—C19—C20	165.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.55	3.404 (3)	153
C6—H6···O1ⁱⁱ	0.93	2.58	3.505 (3)	179

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O
M_r	376.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0342 (3), 17.4069 (4), 9.4392 (2)
β (°)	91.757 (2)
V (Å³)	1976.38 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15074, 3488, 2210
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.167, 1.03
No. of reflections	3488
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.55	3.404 (3)	153
C6—H6···O1ⁱⁱ	0.93	2.58	3.505 (3)	179

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

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (50973077), the Natural Science Foundation of Jiangsu Province Education Committee (11KJA430003), the Project of Persons with Ability of Jiangsu Province (2010-xcl-015) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for financial support.

References

Bruker (2007). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, C.-B., Wang, X.-M., Wang, X.-H. & Luo, J.-F. (2012). Opt. Mater. 34, 609–615. Web of Science CrossRef CAS Google Scholar
He, G.-S., Tan, L.-S., Zheng, Q.-D. & Prasad, P.-N. (2008). Chem. Rev. 108, 1245-1330. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar