N-(Anthracen-9-ylmeth­yl)adamantan-1-amine

Fan, W.-Q.; Chen, F.-X.

doi:10.1107/S1600536812022106

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1831

doi:10.1107/S1600536812022106

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N-(Anthracen-9-ylmethyl)adamantan-1-amine

Wei-Qiang Fan ^a ^* and Fu-Xiao Chen ^b

^aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212023, People's Republic of China, and ^bSchool of the Environment, Jiangsu University, Zhenjiang 212023, People's Republic of China
^*Correspondence e-mail: fwq4993329@ujs.edu.cn

(Received 29 March 2012; accepted 16 May 2012; online 19 May 2012)

In the crystal stucture of the of the title compound, C₂₅H₂₇N, stong π–π interactions are found between adjacent anthracene fragments, with a shortest centroid–centroid distance of 3.5750 (9) Å.

Related literature

Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH sensors, see: Bernhardt et al. (2001 ), Chen & Chen (2004 ); Gunnlaugsson et al. (2003 ); Kim & Yoon (2002 )

Experimental

Crystal data

C₂₅H₂₇N
M_r = 341.26
Orthorhombic, P c c n
a = 9.9546 (4) Å
b = 42.1921 (19) Å
c = 8.6133 (4) Å
V = 3617.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.35 × 0.24 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.975, T_max = 0.998
18689 measured reflections
3594 independent reflections
3089 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.03
3594 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022106/aa2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022106/aa2056Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022106/aa2056Isup3.cml

checkCIF report

Comment top

Anthracene derivatives have been widely used in the field of anion recognition, metal ionfluorescent sensors, as well as pH sensors (Gunnlaugsson et al., 2003; Chen & Chen, 2004; Kim & Yoon, 2002; Bernhardt et al. 2001) because of their excellent photophysical properties and high fluorescence.

In the crystals of the title compound (Fig. 1), there are two π–π interactions between benzene rings of the ajacent anthracene fragments with the distances Cg1···Cg2ⁱ = 3.5750 (9) Å and Cg1···Cg3ⁱ = 4.0043 (10) Å. (Cg1, Cg2 and Cg3 are the centroids of the rings [C1/C5 and C14], [C5/C7 and C12/C14] and [C7/C12], respectively; symmetry code: (i) 1/2 - x, y, z + 1/2) forming one-dimensional supramolecular chains along c axis direction (Fig. 2).

Related literature top

Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH sensors, see: Bernhardt et al. (2001), Chen & Chen (2004); Gunnlaugsson et al. (2003); Kim & Yoon (2002)

Experimental top

9-Anthracenecarboxaldehyde (2.06 g, 10 mmol) was added into a solution of amantadine (1.51 g, 10 mmol) in ethanol. Yellow precipitate was formed atfer string for 1 h. The yellow Schiff base was filtrated and dryed. NaBH₄ (7.56 g, 20 mmol) was added into a solution of the Schiff base in anhydrous methanol (120 ml). After 3 h, the white solid, 9-[(adamantan-1-ylamino)methyl]anthracene, was obtained by reduced pressure distillation, extraction and drying. The colourless block-shaped crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from ethanol.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Thermal displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The one-dimensional supramolecular chains linked by π–π interactions. H atoms are omitted for clarity.

N-(Anthracen-9-ylmethyl)adamantan-1-amine top

Crystal data top

C₂₅H₂₇N	F(000) = 1472
M_r = 341.26	D_x = 1.253 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3594 reflections
a = 9.9546 (4) Å	θ = 1.0–26.0°
b = 42.1921 (19) Å	µ = 0.07 mm⁻¹
c = 8.6133 (4) Å	T = 293 K
V = 3617.6 (3) Å³	Block, colorless
Z = 8	0.35 × 0.24 × 0.20 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	3594 independent reflections
Radiation source: fine-focus sealed tube	3089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 26.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→12
T_min = 0.975, T_max = 0.998	k = −52→50
18689 measured reflections	l = −10→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0431P)² + 1.8749P] where P = (F_o² + 2F_c²)/3
3594 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₅H₂₇N	V = 3617.6 (3) Å³
M_r = 341.26	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 9.9546 (4) Å	µ = 0.07 mm⁻¹
b = 42.1921 (19) Å	T = 293 K
c = 8.6133 (4) Å	0.35 × 0.24 × 0.20 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	3594 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3089 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.998	R_int = 0.037
18689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
3594 reflections	Δρ_min = −0.20 e Å⁻³
238 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.07687 (14)	0.06244 (3)	0.02106 (16)	0.0213 (3)
H1	0.0190	0.0763	0.0720	0.026*
C2	0.02463 (14)	0.03905 (3)	−0.06924 (16)	0.0251 (3)
H2	−0.0681	0.0372	−0.0795	0.030*
C3	0.10948 (15)	0.01740 (3)	−0.14794 (16)	0.0263 (3)
H3	0.0724	0.0015	−0.2089	0.032*
C4	0.24486 (15)	0.01993 (3)	−0.13433 (15)	0.0239 (3)
H4	0.2998	0.0057	−0.1866	0.029*
C5	0.30441 (14)	0.04417 (3)	−0.04106 (15)	0.0189 (3)
C6	0.44299 (14)	0.04664 (3)	−0.02481 (15)	0.0206 (3)
H6	0.4980	0.0321	−0.0753	0.025*
C7	0.50153 (13)	0.07034 (3)	0.06532 (15)	0.0192 (3)
C8	0.64357 (14)	0.07199 (3)	0.08598 (18)	0.0275 (3)
H8	0.6984	0.0572	0.0370	0.033*
C9	0.70002 (15)	0.09479 (3)	0.1760 (2)	0.0320 (4)
H9	0.7925	0.0951	0.1911	0.038*
C10	0.61811 (14)	0.11826 (3)	0.24708 (17)	0.0266 (3)
H10	0.6577	0.1342	0.3061	0.032*
C11	0.48252 (13)	0.11763 (3)	0.22964 (15)	0.0201 (3)
H11	0.4309	0.1334	0.2755	0.024*
C12	0.41699 (13)	0.09318 (3)	0.14216 (14)	0.0165 (3)
C13	0.27606 (13)	0.09040 (3)	0.13158 (14)	0.0164 (3)
C14	0.21886 (13)	0.06624 (3)	0.03960 (14)	0.0177 (3)
C15	0.18568 (13)	0.11250 (3)	0.22289 (14)	0.0173 (3)
H15A	0.1067	0.1010	0.2570	0.021*
H15B	0.2330	0.1199	0.3145	0.021*
C16	0.07339 (12)	0.16531 (3)	0.21643 (14)	0.0148 (3)
C17	−0.03739 (12)	0.15278 (3)	0.32484 (14)	0.0161 (3)
H17A	−0.1027	0.1409	0.2647	0.019*
H17B	0.0018	0.1385	0.4007	0.019*
C18	−0.10802 (12)	0.18021 (3)	0.40888 (15)	0.0178 (3)
H18	−0.1777	0.1717	0.4777	0.021*
C19	−0.17216 (13)	0.20239 (3)	0.28916 (16)	0.0211 (3)
H19A	−0.2167	0.2198	0.3417	0.025*
H19B	−0.2389	0.1909	0.2293	0.025*
C20	−0.06276 (13)	0.21533 (3)	0.18062 (16)	0.0204 (3)
H20	−0.1037	0.2294	0.1034	0.024*
C21	0.04073 (13)	0.23400 (3)	0.27656 (16)	0.0214 (3)
H21A	0.1096	0.2425	0.2087	0.026*
H21B	−0.0030	0.2516	0.3287	0.026*
C22	0.10463 (13)	0.21183 (3)	0.39676 (15)	0.0193 (3)
H22	0.1706	0.2237	0.4581	0.023*
C23	0.17531 (12)	0.18428 (3)	0.31292 (15)	0.0172 (3)
H23A	0.2450	0.1926	0.2454	0.021*
H23B	0.2174	0.1705	0.3887	0.021*
C24	0.00819 (13)	0.18773 (3)	0.09765 (15)	0.0185 (3)
H24A	−0.0565	0.1761	0.0357	0.022*
H24B	0.0766	0.1960	0.0285	0.022*
C25	−0.00415 (13)	0.19856 (3)	0.50496 (15)	0.0191 (3)
H25A	0.0364	0.1846	0.5811	0.023*
H25B	−0.0479	0.2158	0.5598	0.023*
N1	0.14369 (11)	0.14005 (2)	0.12914 (12)	0.0168 (2)
H1N	0.0920 (15)	0.1338 (3)	0.0533 (16)	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0250 (7)	0.0178 (6)	0.0210 (7)	0.0004 (5)	0.0014 (5)	0.0045 (5)
C2	0.0253 (7)	0.0248 (7)	0.0253 (7)	−0.0064 (6)	−0.0025 (6)	0.0061 (6)
C3	0.0386 (8)	0.0200 (7)	0.0204 (7)	−0.0101 (6)	−0.0025 (6)	0.0001 (5)
C4	0.0371 (8)	0.0158 (6)	0.0189 (7)	−0.0018 (6)	0.0031 (6)	−0.0011 (5)
C5	0.0282 (7)	0.0130 (6)	0.0155 (6)	−0.0009 (5)	0.0019 (5)	0.0020 (5)
C6	0.0272 (7)	0.0143 (6)	0.0204 (7)	0.0037 (5)	0.0065 (5)	−0.0012 (5)
C7	0.0231 (7)	0.0146 (6)	0.0199 (7)	0.0013 (5)	0.0042 (5)	0.0016 (5)
C8	0.0223 (7)	0.0218 (7)	0.0384 (9)	0.0026 (5)	0.0077 (6)	−0.0037 (6)
C9	0.0195 (7)	0.0279 (7)	0.0488 (10)	−0.0032 (6)	0.0031 (7)	−0.0058 (7)
C10	0.0268 (7)	0.0208 (7)	0.0323 (8)	−0.0067 (5)	0.0014 (6)	−0.0042 (6)
C11	0.0257 (7)	0.0146 (6)	0.0201 (7)	0.0000 (5)	0.0038 (5)	0.0003 (5)
C12	0.0229 (6)	0.0119 (6)	0.0147 (6)	0.0009 (5)	0.0024 (5)	0.0022 (5)
C13	0.0231 (7)	0.0120 (5)	0.0139 (6)	0.0021 (5)	0.0023 (5)	0.0041 (5)
C14	0.0240 (7)	0.0138 (6)	0.0152 (6)	0.0004 (5)	0.0017 (5)	0.0044 (5)
C15	0.0203 (6)	0.0151 (6)	0.0165 (6)	0.0013 (5)	0.0021 (5)	0.0015 (5)
C16	0.0168 (6)	0.0124 (6)	0.0153 (6)	0.0010 (5)	0.0002 (5)	−0.0002 (5)
C17	0.0173 (6)	0.0141 (6)	0.0170 (6)	−0.0018 (5)	0.0009 (5)	−0.0005 (5)
C18	0.0176 (6)	0.0165 (6)	0.0192 (6)	−0.0003 (5)	0.0038 (5)	−0.0013 (5)
C19	0.0179 (6)	0.0209 (6)	0.0246 (7)	0.0044 (5)	−0.0008 (5)	−0.0036 (5)
C20	0.0249 (7)	0.0156 (6)	0.0207 (7)	0.0052 (5)	−0.0020 (5)	0.0027 (5)
C21	0.0259 (7)	0.0129 (6)	0.0254 (7)	0.0006 (5)	0.0025 (6)	0.0008 (5)
C22	0.0206 (6)	0.0146 (6)	0.0226 (7)	−0.0029 (5)	−0.0024 (5)	−0.0028 (5)
C23	0.0158 (6)	0.0153 (6)	0.0206 (7)	−0.0008 (5)	−0.0005 (5)	0.0016 (5)
C24	0.0215 (6)	0.0180 (6)	0.0160 (6)	0.0020 (5)	−0.0006 (5)	0.0012 (5)
C25	0.0256 (7)	0.0145 (6)	0.0171 (6)	0.0019 (5)	−0.0006 (5)	−0.0022 (5)
N1	0.0212 (6)	0.0145 (5)	0.0147 (5)	0.0037 (4)	−0.0003 (4)	0.0002 (4)

Geometric parameters (Å, º) top

C1—C2	1.3598 (19)	C16—N1	1.4800 (15)
C1—C14	1.4314 (19)	C16—C23	1.5364 (16)
C1—H1	0.9300	C16—C24	1.5373 (16)
C2—C3	1.417 (2)	C16—C17	1.5387 (16)
C2—H2	0.9300	C17—C18	1.5355 (16)
C3—C4	1.357 (2)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.4291 (18)	C18—C19	1.5318 (18)
C4—H4	0.9300	C18—C25	1.5339 (17)
C5—C6	1.3905 (19)	C18—H18	0.9800
C5—C14	1.4407 (18)	C19—C20	1.5357 (18)
C6—C7	1.3937 (18)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C8	1.4268 (19)	C20—C24	1.5378 (17)
C7—C12	1.4403 (17)	C20—C21	1.5379 (18)
C8—C9	1.357 (2)	C20—H20	0.9800
C8—H8	0.9300	C21—C22	1.5335 (18)
C9—C10	1.422 (2)	C21—H21A	0.9700
C9—H9	0.9300	C21—H21B	0.9700
C10—C11	1.3584 (19)	C22—C25	1.5346 (18)
C10—H10	0.9300	C22—C23	1.5389 (17)
C11—C12	1.4346 (17)	C22—H22	0.9800
C11—H11	0.9300	C23—H23A	0.9700
C12—C13	1.4107 (18)	C23—H23B	0.9700
C13—C14	1.4110 (17)	C24—H24A	0.9700
C13—C15	1.5155 (16)	C24—H24B	0.9700
C15—N1	1.4760 (15)	C25—H25A	0.9700
C15—H15A	0.9700	C25—H25B	0.9700
C15—H15B	0.9700	N1—H1N	0.873 (13)

C2—C1—C14	121.52 (13)	C16—C17—H17A	109.5
C2—C1—H1	119.2	C18—C17—H17B	109.5
C14—C1—H1	119.2	C16—C17—H17B	109.5
C1—C2—C3	120.90 (13)	H17A—C17—H17B	108.1
C1—C2—H2	119.6	C19—C18—C25	109.63 (10)
C3—C2—H2	119.5	C19—C18—C17	109.51 (10)
C4—C3—C2	120.00 (12)	C25—C18—C17	109.03 (10)
C4—C3—H3	120.0	C19—C18—H18	109.6
C2—C3—H3	120.0	C25—C18—H18	109.6
C3—C4—C5	121.12 (13)	C17—C18—H18	109.6
C3—C4—H4	119.4	C18—C19—C20	109.35 (10)
C5—C4—H4	119.4	C18—C19—H19A	109.8
C6—C5—C4	121.45 (12)	C20—C19—H19A	109.8
C6—C5—C14	119.30 (12)	C18—C19—H19B	109.8
C4—C5—C14	119.24 (12)	C20—C19—H19B	109.8
C5—C6—C7	121.65 (12)	H19A—C19—H19B	108.3
C5—C6—H6	119.2	C19—C20—C24	109.84 (10)
C7—C6—H6	119.2	C19—C20—C21	109.27 (11)
C6—C7—C8	121.25 (12)	C24—C20—C21	109.26 (10)
C6—C7—C12	119.45 (12)	C19—C20—H20	109.5
C8—C7—C12	119.29 (12)	C24—C20—H20	109.5
C9—C8—C7	121.07 (13)	C21—C20—H20	109.5
C9—C8—H8	119.5	C22—C21—C20	109.15 (10)
C7—C8—H8	119.5	C22—C21—H21A	109.8
C8—C9—C10	120.16 (13)	C20—C21—H21A	109.8
C8—C9—H9	119.9	C22—C21—H21B	109.8
C10—C9—H9	119.9	C20—C21—H21B	109.8
C11—C10—C9	120.58 (13)	H21A—C21—H21B	108.3
C11—C10—H10	119.7	C21—C22—C25	109.87 (11)
C9—C10—H10	119.7	C21—C22—C23	109.49 (10)
C10—C11—C12	121.59 (12)	C25—C22—C23	109.38 (10)
C10—C11—H11	119.2	C21—C22—H22	109.4
C12—C11—H11	119.2	C25—C22—H22	109.4
C13—C12—C11	123.08 (11)	C23—C22—H22	109.4
C13—C12—C7	119.73 (11)	C16—C23—C22	110.21 (10)
C11—C12—C7	117.18 (12)	C16—C23—H23A	109.6
C12—C13—C14	119.83 (11)	C22—C23—H23A	109.6
C12—C13—C15	120.39 (11)	C16—C23—H23B	109.6
C14—C13—C15	119.75 (11)	C22—C23—H23B	109.6
C13—C14—C1	122.83 (12)	H23A—C23—H23B	108.1
C13—C14—C5	119.96 (12)	C16—C24—C20	110.53 (10)
C1—C14—C5	117.21 (12)	C16—C24—H24A	109.5
N1—C15—C13	111.64 (10)	C20—C24—H24A	109.5
N1—C15—H15A	109.3	C16—C24—H24B	109.5
C13—C15—H15A	109.3	C20—C24—H24B	109.5
N1—C15—H15B	109.3	H24A—C24—H24B	108.1
C13—C15—H15B	109.3	C18—C25—C22	109.40 (10)
H15A—C15—H15B	108.0	C18—C25—H25A	109.8
N1—C16—C23	109.73 (10)	C22—C25—H25A	109.8
N1—C16—C24	107.74 (10)	C18—C25—H25B	109.8
C23—C16—C24	108.55 (10)	C22—C25—H25B	109.8
N1—C16—C17	113.57 (9)	H25A—C25—H25B	108.2
C23—C16—C17	108.90 (10)	C15—N1—C16	115.03 (9)
C24—C16—C17	108.22 (10)	C15—N1—H1N	109.8 (10)
C18—C17—C16	110.81 (10)	C16—N1—H1N	108.6 (10)
C18—C17—H17A	109.5

C14—C1—C2—C3	0.3 (2)	C12—C13—C15—N1	94.66 (13)
C1—C2—C3—C4	−0.3 (2)	C14—C13—C15—N1	−87.49 (13)
C2—C3—C4—C5	0.2 (2)	N1—C16—C17—C18	−178.78 (10)
C3—C4—C5—C6	179.09 (13)	C23—C16—C17—C18	58.63 (13)
C3—C4—C5—C14	−0.04 (19)	C24—C16—C17—C18	−59.20 (13)
C4—C5—C6—C7	179.63 (12)	C16—C17—C18—C19	60.18 (13)
C14—C5—C6—C7	−1.24 (19)	C16—C17—C18—C25	−59.77 (13)
C5—C6—C7—C8	177.65 (13)	C25—C18—C19—C20	60.30 (13)
C5—C6—C7—C12	−0.85 (19)	C17—C18—C19—C20	−59.28 (13)
C6—C7—C8—C9	−178.87 (14)	C18—C19—C20—C24	59.26 (13)
C12—C7—C8—C9	−0.4 (2)	C18—C19—C20—C21	−60.59 (13)
C7—C8—C9—C10	−2.3 (2)	C19—C20—C21—C22	60.28 (13)
C8—C9—C10—C11	1.9 (2)	C24—C20—C21—C22	−59.93 (13)
C9—C10—C11—C12	1.2 (2)	C20—C21—C22—C25	−59.94 (13)
C10—C11—C12—C13	174.98 (13)	C20—C21—C22—C23	60.21 (13)
C10—C11—C12—C7	−3.74 (19)	N1—C16—C23—C22	176.69 (10)
C6—C7—C12—C13	3.06 (18)	C24—C16—C23—C22	59.19 (13)
C8—C7—C12—C13	−175.46 (12)	C17—C16—C23—C22	−58.43 (12)
C6—C7—C12—C11	−178.18 (11)	C21—C22—C23—C16	−60.42 (13)
C8—C7—C12—C11	3.30 (18)	C25—C22—C23—C16	60.03 (13)
C11—C12—C13—C14	178.18 (11)	N1—C16—C24—C20	−178.02 (10)
C7—C12—C13—C14	−3.14 (17)	C23—C16—C24—C20	−59.25 (13)
C11—C12—C13—C15	−3.97 (18)	C17—C16—C24—C20	58.80 (13)
C7—C12—C13—C15	174.71 (11)	C19—C20—C24—C16	−59.76 (13)
C12—C13—C14—C1	−178.69 (11)	C21—C20—C24—C16	60.10 (13)
C15—C13—C14—C1	3.44 (17)	C19—C18—C25—C22	−59.63 (13)
C12—C13—C14—C5	1.06 (17)	C17—C18—C25—C22	60.24 (13)
C15—C13—C14—C5	−176.81 (11)	C21—C22—C25—C18	59.59 (13)
C2—C1—C14—C13	179.54 (12)	C23—C22—C25—C18	−60.63 (13)
C2—C1—C14—C5	−0.22 (18)	C13—C15—N1—C16	−170.68 (10)
C6—C5—C14—C13	1.15 (18)	C23—C16—N1—C15	75.36 (12)
C4—C5—C14—C13	−179.70 (11)	C24—C16—N1—C15	−166.62 (10)
C6—C5—C14—C1	−179.09 (11)	C17—C16—N1—C15	−46.77 (14)
C4—C5—C14—C1	0.06 (17)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₇N
M_r	341.26
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	9.9546 (4), 42.1921 (19), 8.6133 (4)
V (Å³)	3617.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.35 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.975, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	18689, 3594, 3089
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.03
No. of reflections	3594
No. of parameters	238
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Acknowledgements

We thank the Start-up Foundation for Advanced Professionals of Jiangsu University (11JDG105) for support.

References

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