4-Amino-13-(1-naphth­yl)-[2,2]paracyclo­phane

Sun, J.; Huo, Y.; Wu, R.; Li, J.; Ma, Y.

doi:10.1107/S1600536808005333

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o650

doi:10.1107/S1600536808005333

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4-Amino-13-(1-naphthyl)-[2,2]paracyclophane

Junshan Sun,^a Yanmin Huo,^b Rentao Wu,^c Jikun Li ^a and Yudao Ma ^d ^*

^aDepartment of Materials and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China, ^bShandong Institute of Supervision & Inspection of Product Quality, 250100 Jinan, Shandong, People's Republic of China, ^cDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^dDepartment of Chemistry, Shandong University, 250100 Jinan, Shandong, People's Republic of China
^*Correspondence e-mail: ydma@sdu.edu.cn

(Received 5 November 2007; accepted 25 February 2008; online 5 March 2008)

The title compound [systematic name: 1²-amino-4²-(1-naphthyl)-1,4(1,4)-dibenzenacyclohexaphane], C₂₆H₂₃N, was synthesized from 4-amino-13-bromo-[2,2]paracyclophane and 1-naphthaleneboronic acid in the presence of 1,4-dioxane. It is a new cyclophane-derived compound which can be regarded as a prospective ligand for asymmetric synthesis and catalysis. The benzene rings of the paracyclophane units are very slightly deformed from planarity as shallow boats.

Related literature

For related literature on paracyclophane chemistry, see: Cipiciani et al. (1997 ); on diphosphanes, see: Pye et al. (1997 ); on oxazoline-phosphanes, see: Wu et al. (2003 ); on oxazoline-imidazolium, see: Bolm et al. (2003 ); on oxazoline-selenides, see: Hou et al. (2000 ); on oxazoline-alcohols, see: Wu et al. (2001 ).

Experimental

Crystal data

C₂₆H₂₃N
M_r = 349.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.5261 (5) Å
b = 12.8123 (8) Å
c = 17.2065 (11) Å
V = 1879.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.990, T_max = 0.993
9879 measured reflections
1901 independent reflections
1690 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.159
S = 1.00
1901 reflections
245 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005333/kj2079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005333/kj2079Isup2.hkl

checkCIF report

Comment top

The chemistry of [2.2]paracyclophanes has attracted the interest of researchers since the middle of the last century. After a standstill period, investigations in this area have received a new impulse (Cipiciani et al., 1997) and recently there has been notable progress especially regarding the synthesis of new derivatives. [2.2]paracyclophane is unique as the strain in the molecule has become so large that the benzene rings have been substantially bent from planarity. The configurationally rigid [2. 2]paracyclophanyl unit makes the design of chiral ligands of different types possible. The [2.2]paracyclophane ligand has previously been included in diphosphanes, (Pye et al., 1997) oxazoline-phosphanes,(Wu et al., 2003) oxazoline-imidazolium,(Bolm et al., 2003) oxazoline-selenides, (Hou et al., 2000) oxazoline-alcohols,(Wu et al., 2001) and Schiff base phenols.

The benzene rings in the [2,2] paracyclophane are not planar. Their conformation can be described as an asymmetric boat conformation. The benzene C atoms which are directly bonded to the ethylene links of the paracyclophane deviate significantly from the least-squares planes running through the other four benzene C atoms. The largest deviations are found for the atoms C3 [0.117 (5) Å] and C12 [0.146 (4) Å], which are the atoms closest to the amino and naphtyl substituents of the benzene rings. The angle between the planes through the benzene rings is 6.0 (2) °. The N1—C1 bond length lies between the expected values for a C—N and a C=N bond, which is probably caused by p–π conjugation.

Related literature top

For related literature on paracyclophane chemistry, see: Cipiciani et al. (1997); on diphosphanes, see: Pye et al. (1997); on oxazoline-phosphanes, see: Wu et al. (2003); on oxazoline-imidazolium, see: Bolm et al. (2003); on oxazoline-selenides, see: Hou et al. (2000); on oxazoline-alcohols, see: Wu et al. (2001).

Experimental top

A solution of 4-amino-13-bromo [2,2]paracyclophane (501.3 mg, 1.66 mmol), 1-naphthaleneboronic acid (428.3 mg, 2.49 mmol), KF (289.7 mg, 4.98 mmol), Pd-DPPF (13.6 mg, 0.0166 mmol) in 1,4-dioxane (5 ml) was stirred at 353–363k for 24 h under a slight overpressure of nitrogen. After this, reagents were added to the mixture at 24 h intervals. 1-naphthaleneboronic acid (0.55 mmol), KF (72.4 mg, 1.245 mmol), Pd-DPPF (13.6 mg, 0.0166 mmol) were added to the flask in the first two times, in the last two times, 1-naphthaleneboronic acid (0.55 mmol), KF (72.4 mg, 1.245 mmol), Pd-DPPF (6.78 mg, 0.0083 mmol) were added. The flask was kept at 353–363 K and stirred the whole time. After completion of the reaction, as indicated by TLC, water (5 ml) was added and the solution was filtered. The solution was extracted by dichloromethane (30 ml) and the solvent was removed on a rotary evaporator. The solid was subjected to chromatography on silica gel (eluent: petroleum ether / ethyl acetate =20:1). Pure product was isolated (yield 84.6%). Analysis, calculated for C₂₆H₂₃N: C, 89.36; H, 6.63; N, 4.01. Found: C, 89.03; H, 6.62; N, 3.93. The elemental analyses were performed with a Perkin Elmer PE2400II.

Computing details top

Data collection: APEX2 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted.

1²-amino-4²-(1-naphthyl)-1,4(1,4)-dibenzenacyclohexaphane top

Crystal data top

C₂₆H₂₃N	D_x = 1.235 Mg m⁻³
M_r = 349.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3936 reflections
a = 8.5261 (5) Å	θ = 2.7–25.1°
b = 12.8123 (8) Å	µ = 0.07 mm⁻¹
c = 17.2065 (11) Å	T = 293 K
V = 1879.6 (2) Å³	Block, colorless
Z = 4	0.15 × 0.12 × 0.10 mm
F(000) = 744

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1901 independent reflections
Radiation source: fine-focus sealed tube	1690 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
T_min = 0.990, T_max = 0.993	k = −14→15
9879 measured reflections	l = −12→20

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0986P)² + 0.8216P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.005
1901 reflections	Δρ_max = 0.37 e Å⁻³
245 parameters	Δρ_min = −0.33 e Å⁻³
6 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: 0.022 (5)

Crystal data top

C₂₆H₂₃N	V = 1879.6 (2) Å³
M_r = 349.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5261 (5) Å	µ = 0.07 mm⁻¹
b = 12.8123 (8) Å	T = 293 K
c = 17.2065 (11) Å	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1901 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1690 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.993	R_int = 0.026
9879 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	6 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
1901 reflections	Δρ_min = −0.33 e Å⁻³
245 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
N1	0.2691 (6)	0.4913 (3)	0.2196 (3)	0.0659 (12)
H1A	0.2007	0.5066	0.2545	0.079*
H1B	0.3499	0.5306	0.2131	0.079*
C1	0.2490 (5)	0.4028 (3)	0.1733 (2)	0.0497 (11)
C2	0.1199 (5)	0.3383 (4)	0.1826 (3)	0.0561 (12)
H2	0.0486	0.3532	0.2219	0.067*
C3	0.0935 (6)	0.2543 (4)	0.1365 (3)	0.0628 (13)
C4	0.1940 (7)	0.2352 (4)	0.0744 (3)	0.0683 (15)
H4	0.1728	0.1820	0.0392	0.082*
C5	0.3267 (7)	0.2972 (4)	0.0662 (3)	0.0628 (14)
H5	0.3937	0.2856	0.0244	0.075*
C6	0.3618 (6)	0.3758 (4)	0.1187 (2)	0.0515 (11)
C7	0.0003 (7)	0.1612 (5)	0.1707 (4)	0.0833 (19)
H7A	−0.0545	0.1263	0.1287	0.100*
H7B	−0.0782	0.1882	0.2063	0.100*
C8	0.1025 (7)	0.0790 (4)	0.2147 (4)	0.0692 (15)
H8A	0.0486	0.0596	0.2622	0.083*
H8B	0.1106	0.0169	0.1827	0.083*
C9	0.2692 (6)	0.1156 (3)	0.2358 (3)	0.0517 (11)
C10	0.3837 (6)	0.1093 (3)	0.1808 (3)	0.0539 (12)
H10	0.3753	0.0595	0.1417	0.065*
C11	0.5102 (6)	0.1742 (3)	0.1817 (3)	0.0515 (11)
H11	0.5909	0.1640	0.1461	0.062*
C12	0.5201 (5)	0.2548 (3)	0.2347 (2)	0.0417 (10)
C13	0.4179 (5)	0.2553 (3)	0.2981 (2)	0.0394 (9)
C14	0.2894 (5)	0.1865 (3)	0.2960 (2)	0.0465 (10)
H14	0.2162	0.1885	0.3361	0.056*
C15	0.6056 (5)	0.3547 (4)	0.2093 (3)	0.0504 (11)
H15A	0.7152	0.3386	0.2001	0.061*
H15B	0.6005	0.4055	0.2510	0.061*
C16	0.5336 (6)	0.4041 (4)	0.1335 (3)	0.0585 (13)
H16A	0.5423	0.4794	0.1370	0.070*
H16B	0.5955	0.3816	0.0892	0.070*
C17	0.4316 (5)	0.3268 (3)	0.3660 (2)	0.0442 (10)
C18	0.3029 (6)	0.3795 (4)	0.3928 (3)	0.0567 (12)
H18	0.2071	0.3686	0.3683	0.068*
C19	0.3088 (8)	0.4494 (5)	0.4558 (3)	0.0711 (16)
H19	0.2190	0.4849	0.4713	0.085*
C20	0.4445 (9)	0.4643 (5)	0.4931 (3)	0.0748 (18)
H20	0.4484	0.5109	0.5345	0.090*
C21	0.5830 (7)	0.4106 (4)	0.4706 (3)	0.0630 (15)
C22	0.5777 (6)	0.3395 (4)	0.4069 (2)	0.0479 (11)
C23	0.7156 (6)	0.2835 (4)	0.3886 (3)	0.0599 (13)
H23	0.7143	0.2352	0.3482	0.072*
C24	0.8502 (7)	0.2994 (5)	0.4293 (4)	0.0771 (18)
H24	0.9397	0.2614	0.4170	0.093*
C25	0.8549 (10)	0.3729 (6)	0.4899 (4)	0.091 (2)
H25	0.9485	0.3850	0.5162	0.109*
C26	0.7244 (9)	0.4258 (5)	0.5102 (3)	0.080 (2)
H26	0.7285	0.4732	0.5512	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.069 (3)	0.048 (2)	0.081 (3)	0.005 (2)	−0.001 (2)	−0.009 (2)
C1	0.055 (3)	0.042 (2)	0.052 (2)	0.007 (2)	−0.010 (2)	0.009 (2)
C2	0.044 (2)	0.055 (3)	0.069 (3)	0.007 (2)	−0.011 (2)	0.005 (2)
C3	0.054 (3)	0.062 (3)	0.073 (3)	−0.001 (3)	−0.022 (3)	0.002 (3)
C4	0.084 (4)	0.060 (3)	0.061 (3)	−0.001 (3)	−0.033 (3)	−0.006 (3)
C5	0.081 (3)	0.072 (3)	0.036 (2)	−0.002 (3)	−0.005 (2)	0.002 (2)
C6	0.063 (3)	0.051 (2)	0.041 (2)	−0.006 (2)	−0.003 (2)	0.012 (2)
C7	0.059 (3)	0.075 (4)	0.116 (5)	−0.024 (3)	−0.026 (4)	0.002 (4)
C8	0.072 (3)	0.052 (3)	0.083 (3)	−0.026 (3)	−0.013 (3)	−0.002 (3)
C9	0.062 (3)	0.035 (2)	0.058 (2)	−0.008 (2)	−0.011 (2)	0.0041 (19)
C10	0.068 (3)	0.034 (2)	0.060 (3)	0.005 (2)	−0.011 (2)	−0.009 (2)
C11	0.055 (3)	0.044 (2)	0.055 (2)	0.011 (2)	0.000 (2)	−0.007 (2)
C12	0.0367 (19)	0.039 (2)	0.049 (2)	0.0018 (18)	−0.0046 (18)	−0.0019 (18)
C13	0.043 (2)	0.0339 (19)	0.042 (2)	0.0011 (17)	−0.0071 (17)	0.0002 (16)
C14	0.052 (2)	0.042 (2)	0.045 (2)	−0.006 (2)	−0.004 (2)	0.0073 (19)
C15	0.042 (2)	0.049 (2)	0.060 (3)	−0.008 (2)	0.010 (2)	−0.003 (2)
C16	0.065 (3)	0.062 (3)	0.049 (2)	−0.016 (3)	0.013 (2)	0.006 (2)
C17	0.054 (2)	0.039 (2)	0.040 (2)	−0.0040 (19)	−0.001 (2)	0.0009 (18)
C18	0.063 (3)	0.055 (3)	0.052 (2)	−0.003 (2)	0.009 (2)	−0.007 (2)
C19	0.087 (4)	0.066 (3)	0.060 (3)	0.004 (3)	0.015 (3)	−0.014 (3)
C20	0.117 (5)	0.060 (3)	0.047 (3)	−0.017 (3)	0.016 (3)	−0.013 (2)
C21	0.096 (4)	0.055 (3)	0.038 (2)	−0.028 (3)	−0.010 (3)	0.009 (2)
C22	0.061 (3)	0.043 (2)	0.040 (2)	−0.013 (2)	−0.009 (2)	0.0080 (18)
C23	0.061 (3)	0.061 (3)	0.057 (3)	−0.004 (2)	−0.017 (2)	0.009 (2)
C24	0.062 (3)	0.085 (4)	0.084 (4)	−0.012 (3)	−0.026 (3)	0.029 (3)
C25	0.101 (5)	0.105 (5)	0.068 (4)	−0.048 (5)	−0.044 (4)	0.026 (4)
C26	0.104 (5)	0.083 (4)	0.054 (3)	−0.035 (4)	−0.028 (3)	0.013 (3)

Geometric parameters (Å, º) top

N1—C1	1.396 (6)	C12—C15	1.537 (6)
N1—H1A	0.8600	C13—C14	1.406 (6)
N1—H1B	0.8600	C13—C17	1.489 (6)
C1—C2	1.386 (7)	C14—H14	0.9300
C1—C6	1.389 (7)	C15—C16	1.574 (7)
C2—C3	1.354 (7)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.391 (8)	C16—H16A	0.9700
C3—C7	1.549 (8)	C16—H16B	0.9700
C4—C5	1.390 (8)	C17—C18	1.369 (6)
C4—H4	0.9300	C17—C22	1.440 (6)
C5—C6	1.385 (7)	C18—C19	1.406 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—C16	1.530 (7)	C19—C20	1.337 (9)
C7—C8	1.563 (8)	C19—H19	0.9300
C7—H7A	0.9700	C20—C21	1.421 (9)
C7—H7B	0.9700	C20—H20	0.9300
C8—C9	1.539 (7)	C21—C26	1.398 (8)
C8—H8A	0.9700	C21—C22	1.426 (7)
C8—H8B	0.9700	C22—C23	1.413 (7)
C9—C10	1.362 (7)	C23—C24	1.360 (7)
C9—C14	1.390 (6)	C23—H23	0.9300
C10—C11	1.362 (7)	C24—C25	1.405 (10)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.381 (6)	C25—C26	1.349 (10)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.395 (6)	C26—H26	0.9300

C1—N1—H1A	120.0	C14—C13—C17	117.8 (4)
C1—N1—H1B	120.0	C9—C14—C13	121.7 (4)
H1A—N1—H1B	120.0	C9—C14—H14	119.2
C2—C1—C6	118.7 (4)	C13—C14—H14	119.2
C2—C1—N1	121.1 (5)	C12—C15—C16	112.7 (4)
C6—C1—N1	120.2 (4)	C12—C15—H15A	109.0
C3—C2—C1	122.6 (5)	C16—C15—H15A	109.0
C3—C2—H2	118.7	C12—C15—H15B	109.0
C1—C2—H2	118.7	C16—C15—H15B	109.0
C2—C3—C4	119.1 (5)	H15A—C15—H15B	107.8
C2—C3—C7	118.3 (5)	C6—C16—C15	114.6 (4)
C4—C3—C7	118.1 (5)	C6—C16—H16A	108.6
C5—C4—C3	118.6 (5)	C15—C16—H16A	108.6
C5—C4—H4	120.7	C6—C16—H16B	108.6
C3—C4—H4	120.7	C15—C16—H16B	108.6
C6—C5—C4	121.7 (5)	H16A—C16—H16B	107.6
C6—C5—H5	119.2	C18—C17—C22	118.2 (4)
C4—C5—H5	119.2	C18—C17—C13	120.4 (4)
C5—C6—C1	118.2 (5)	C22—C17—C13	121.4 (4)
C5—C6—C16	119.2 (5)	C17—C18—C19	123.1 (5)
C1—C6—C16	119.4 (4)	C17—C18—H18	118.5
C3—C7—C8	114.6 (4)	C19—C18—H18	118.5
C3—C7—H7A	108.6	C20—C19—C18	119.4 (6)
C8—C7—H7A	108.6	C20—C19—H19	120.3
C3—C7—H7B	108.6	C18—C19—H19	120.3
C8—C7—H7B	108.6	C19—C20—C21	121.3 (5)
H7A—C7—H7B	107.6	C19—C20—H20	119.3
C9—C8—C7	115.1 (4)	C21—C20—H20	119.3
C9—C8—H8A	108.5	C26—C21—C20	121.1 (5)
C7—C8—H8A	108.5	C26—C21—C22	119.5 (6)
C9—C8—H8B	108.5	C20—C21—C22	119.5 (5)
C7—C8—H8B	108.5	C23—C22—C21	118.0 (4)
H8A—C8—H8B	107.5	C23—C22—C17	123.6 (4)
C10—C9—C14	117.9 (4)	C21—C22—C17	118.4 (5)
C10—C9—C8	118.7 (4)	C24—C23—C22	120.7 (5)
C14—C9—C8	119.3 (5)	C24—C23—H23	119.6
C11—C10—C9	121.6 (4)	C22—C23—H23	119.6
C11—C10—H10	119.2	C23—C24—C25	120.5 (7)
C9—C10—H10	119.2	C23—C24—H24	119.8
C10—C11—C12	120.8 (4)	C25—C24—H24	119.8
C10—C11—H11	119.6	C26—C25—C24	120.3 (6)
C12—C11—H11	119.6	C26—C25—H25	119.8
C11—C12—C13	118.8 (4)	C24—C25—H25	119.8
C11—C12—C15	117.6 (4)	C25—C26—C21	120.9 (6)
C13—C12—C15	121.0 (4)	C25—C26—H26	119.5
C12—C13—C14	117.7 (4)	C21—C26—H26	119.5
C12—C13—C17	124.5 (4)

C6—C1—C2—C3	−5.0 (3)	C11—C12—C15—C16	56.6 (5)
N1—C1—C2—C3	177.2 (4)	C13—C12—C15—C16	−104.9 (5)
C1—C2—C3—C4	−4.0 (3)	C5—C6—C16—C15	−99.3 (5)
C1—C2—C3—C7	152.0 (4)	C1—C6—C16—C15	60.0 (6)
C2—C3—C4—C5	6.0 (5)	C12—C15—C16—C6	24.3 (6)
C7—C3—C4—C5	−150.0 (5)	C12—C13—C17—C18	132.4 (4)
C3—C4—C5—C6	1.0 (6)	C14—C13—C17—C18	−44.7 (5)
C4—C5—C6—C1	−9.9 (6)	C12—C13—C17—C22	−50.0 (6)
C4—C5—C6—C16	149.7 (4)	C14—C13—C17—C22	132.9 (4)
C2—C1—C6—C5	11.8 (5)	C22—C17—C18—C19	3.4 (7)
N1—C1—C6—C5	−170.4 (4)	C13—C17—C18—C19	−178.9 (4)
C2—C1—C6—C16	−147.8 (4)	C17—C18—C19—C20	−1.6 (8)
N1—C1—C6—C16	30.0 (6)	C18—C19—C20—C21	−0.3 (9)
C2—C3—C7—C8	−87.2 (6)	C19—C20—C21—C26	−179.5 (5)
C4—C3—C7—C8	69.0 (7)	C19—C20—C21—C22	0.3 (8)
C3—C7—C8—C9	15.1 (8)	C26—C21—C22—C23	2.8 (7)
C7—C8—C9—C10	−82.7 (6)	C20—C21—C22—C23	−176.9 (5)
C7—C8—C9—C14	74.1 (7)	C26—C21—C22—C17	−178.7 (4)
C14—C9—C10—C11	−3.8 (3)	C20—C21—C22—C17	1.6 (7)
C8—C9—C10—C11	153.4 (4)	C18—C17—C22—C23	175.1 (4)
C9—C10—C11—C12	−5.6 (3)	C13—C17—C22—C23	−2.6 (7)
C10—C11—C12—C13	14.2 (5)	C18—C17—C22—C21	−3.3 (6)
C10—C11—C12—C15	−147.7 (3)	C13—C17—C22—C21	179.0 (4)
C11—C12—C13—C14	−13.1 (5)	C21—C22—C23—C24	−1.8 (7)
C15—C12—C13—C14	148.2 (4)	C17—C22—C23—C24	179.8 (5)
C11—C12—C13—C17	169.7 (4)	C22—C23—C24—C25	−0.7 (8)
C15—C12—C13—C17	−29.0 (6)	C23—C24—C25—C26	2.4 (9)
C10—C9—C14—C13	4.5 (5)	C24—C25—C26—C21	−1.4 (9)
C8—C9—C14—C13	−152.5 (4)	C20—C21—C26—C25	178.5 (5)
C12—C13—C14—C9	4.0 (5)	C22—C21—C26—C25	−1.3 (8)
C17—C13—C14—C9	−178.7 (4)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃N
M_r	349.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.5261 (5), 12.8123 (8), 17.2065 (11)
V (Å³)	1879.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.990, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	9879, 1901, 1690
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.159, 1.00
No. of reflections	1901
No. of parameters	245
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.33

Computer programs: APEX2 (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

N1—C1

1.396 (6)

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant Nos. 20441004, 20671059) and the Department of Science and Technology of Shandong Province is gratefully acknowledged.

References

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