N-(Diphenyl­vinyl­idene)-2,6-diisopropyl­aniline

Imhof, W.

doi:10.1107/S1600536808040397

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o25

doi:10.1107/S1600536808040397

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N-(Diphenylvinylidene)-2,6-diisopropylaniline

Wolfgang Imhof ^a ^*

^aInstitute of Inorganic and Analytical Chemistry, Friedrich Schiller University, August-Bebel-Strasse 2, 07743 Jena, Germany
^*Correspondence e-mail: wolfgang.imhof@uni-jena.de

(Received 19 November 2008; accepted 1 December 2008; online 6 December 2008)

The title compound, C₂₆H₂₇N, was prepared by the elimination of water from N-(2,6-diisopropylphenyl)-2,2-diphenylacetamide. The angle at the central C atom of the cumulene measures 172.5 (4)°. Molecules are connected into infinite chains by intermolecular C—H⋯N interactions.

Related literature

For the synthetic procedure, see: Stevens & Singhal (1964 ). For related structures, see: Naqvi & Wheatley (1970 ); Jochims et al. (1984 ); Kuipers et al. (1989 ). For general background, see: Imhof (1997a ,b ). For properties of weak hydrogen bonds, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

C₂₆H₂₇N
M_r = 353.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.082 (4) Å
b = 14.308 (4) Å
c = 17.790 (2) Å
V = 2057 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 (2) K
0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3554 measured reflections
1853 independent reflections
1531 reflections with I > 2σ(I)
R_int = 0.065
θ_max = 24.0°
3 standard reflections frequency: 120 min intensity decay: <0.1%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 0.82
1853 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.15 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
C5—H5⋯N1ⁱ	0.95	2.72	3.554 (4)	146
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: SET4 (de Boer & Duisenberg, 1984 ); data reduction: MolEN (Enraf–Nonius, 1990 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040397/nc2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040397/nc2125Isup2.hkl

checkCIF report

Comment top

In the course of a study on the organometallic and catalytic chemistry of aromatic imines (Imhof, 1997a,b) we became interested in the reactivity of the vinylogous keteneimines. The latter are prepared by the elimination of water from the corresponding acetamides by P₂O₅ in anhydrous pyridine (Stevens & Singhal, 1964).

As expected the molecular structure of the title compound shows an almost linear cumulene system with an angle of 172.5 (4)° at the central C atom. The bonds C1—C2 and C2—N1 show bond lengths of 1.332 (5) and 1.213 (4) Å, respectively. The dihedral angle between the C1—C8—C14 plane and the aromatic substituent at the imine N atom measures to 52.4 (7)° which means that the substituents at the cumulene system do not show the expected orthogonal arrangement. This is most probably caused by the high steric requirements of the two isopropyl groups in ortho-position. A comparison with related aromatic diphenylvinylidene amines from the literature shows that the corresponding dihedral angle is close to 90° if there is no or just one ortho-substituent present in the aromatic group at nitrogen (p-Br-C₆H₄: 85.6°, Naqvi & Wheatley, 1970; o-Me-C₆H₄: 88.1°, Jochims et al., 1984; p-(N═C═CPh₂)-C₆H₄: 88.4°, Kuipers et al., 1989; p-Me-C₆H₄: 83.9°, Naqvi & Wheatley, 1970). If both ortho-positions are substituted the conformation is no longer orthogonal (o-Me₂-C₆H₃: 51.7°, Jochims et al., 1984) as it is also observed for the title compound. The lone pair at nitrogen is involved in a weak intramolecular hydrogen bond (Desiraju & Steiner, 1999) interaction towards H5 leading to the formation of infinite chains.

Related literature top

For the synthetic procedure, see: Stevens & Singhal (1964). For related structures, see: Naqvi & Wheatley (1970); Jochims et al. (1984); Kuipers et al. (1989). For general background, see: Imhof (1997a,b). For properties of weak hydrogen bonds, see: Desiraju & Steiner (1999).

Experimental top

The title compound was prepared following a literature method (Stevens & Singhal, 1964). A sample of 2 g (5.4 mmol) N-(2,6-Diisopropyl-phenyl)-2,2-diphenyl-acetamide was dissolved in 50 ml of anhydrous pyridine. To this solution 5 g P₂O₅ were added and the mixture was refluxed for 7 h. After cooling the solution was filtered and pyridine was evaporated resulting in a red oily residue. The oil was transferred to a short chromatography column and light petroleum (b.p. 40–60°C) was used to elute a yellow solution of the title compound. Concentration of the solution and cooling to 4°C led to the formation of crystalline material from which the crystal for the structure analysis described herein was collected (yield: 1.56 g, 82%). MS (EI) [m/z, %]: 353 (M⁺, 80), 338 (C₂₅H₂₄N⁺, 22), 186 (C₁₃H₁₆N⁺, 100), 165 (C₁₃H₉⁺, 50), 115 (C₉H₇⁺, 19), 91 (C₇H₇⁺, 37), 77 (C₆H₅⁺, 17), 55 (C₄H₇⁺, 11), 41 (C₃H₅⁺, 35). ¹H NMR (CDCl₃, 298 K) [p.p.m.]: 1.11 (12 H, d, ³J_HH = 6.8 Hz, CH₃), 3.24 (2 H, h, ³J_HH = 6.8 Hz, CH), 7.05–7.34 (15 H, m, CH_ar). ¹³C NMR (CDCl₃, 298 K) [p.p.m.]: 22.4 (CH₃), 28.5 (CH), 72.0 (═C), 123.4 (C_arH), 125.9 (C_arH), 126.3 (C_arH), 127.8 (C_arH), 128.7 (C_arH), 134.8 (C_ar), 136.2 (C_ar), 140.8 (C_ar), 183.4 (═C═).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (Boer et al., 1984); data reduction: MolEN (Enraf–Nonius, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, presenting the labelling scheme and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Infinite chains of the title compound realized by C—H···O hydrogen bonds.

N-(Diphenylvinylidene)-2,6-diisopropylaniline top

Crystal data top

C₂₆H₂₇N	F(000) = 760
M_r = 353.49	D_x = 1.141 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 8.082 (4) Å	θ = 20.9–35.5°
b = 14.308 (4) Å	µ = 0.07 mm⁻¹
c = 17.790 (2) Å	T = 173 K
V = 2057 (1) Å³	Cube, pale yellow
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.065
Radiation source: fine-focus sealed tube	θ_max = 24.0°, θ_min = 1.8°
Graphite monochromator	h = −9→0
ω/2θ scans	k = −16→16
3554 measured reflections	l = 0→20
1853 independent reflections	3 standard reflections every 120 min
1531 reflections with I > 2σ(I)	intensity decay: <0.1%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.1319P)² + 0.5946P] where P = (F_o² + 2F_c²)/3
1853 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₆H₂₇N	V = 2057 (1) Å³
M_r = 353.49	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.082 (4) Å	µ = 0.07 mm⁻¹
b = 14.308 (4) Å	T = 173 K
c = 17.790 (2) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.065
3554 measured reflections	θ_max = 24.0°
1853 independent reflections	3 standard reflections every 120 min
1531 reflections with I > 2σ(I)	intensity decay: <0.1%

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 0.82	Δρ_max = 0.15 e Å⁻³
1853 reflections	Δρ_min = −0.17 e Å⁻³
248 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 on F² for ALL reflections except for 9 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.1809 (3)	0.90928 (16)	0.93459 (13)	0.0304 (6)
C1	0.2195 (4)	1.06100 (19)	1.00668 (17)	0.0303 (7)
C2	0.1892 (4)	0.98254 (19)	0.96930 (15)	0.0306 (7)
C3	0.1148 (4)	0.9958 (2)	1.12860 (17)	0.0363 (7)
H3	0.0626	0.9470	1.1012	0.044*
C4	0.1008 (4)	0.9981 (2)	1.20605 (18)	0.0421 (8)
H4	0.0401	0.9508	1.2314	0.051*
C5	0.1749 (4)	1.0691 (2)	1.24668 (18)	0.0414 (8)
H5	0.1636	1.0717	1.2998	0.050*
C6	0.2652 (4)	1.1358 (2)	1.20919 (18)	0.0408 (8)
H6	0.3178	1.1841	1.2370	0.049*
C7	0.2810 (4)	1.1341 (2)	1.13188 (16)	0.0339 (7)
H7	0.3444	1.1807	1.1071	0.041*
C8	0.2041 (4)	1.06391 (18)	1.09007 (17)	0.0289 (6)
C9	0.1828 (5)	1.2310 (2)	0.97473 (17)	0.0404 (8)
H9	0.1050	1.2370	1.0144	0.049*
C10	0.2210 (5)	1.3071 (2)	0.9299 (2)	0.0494 (9)
H10	0.1695	1.3656	0.9395	0.059*
C11	0.3325 (6)	1.2993 (3)	0.87148 (19)	0.0569 (11)
H11	0.3577	1.3521	0.8411	0.068*
C12	0.4071 (5)	1.2144 (3)	0.85749 (19)	0.0544 (10)
H12	0.4830	1.2085	0.8170	0.065*
C13	0.3720 (4)	1.1378 (2)	0.90200 (17)	0.0408 (8)
H13	0.4248	1.0797	0.8923	0.049*
C14	0.2595 (4)	1.1454 (2)	0.96113 (15)	0.0314 (6)
C15	0.0304 (4)	0.7690 (2)	0.90761 (15)	0.0300 (7)
C16	−0.1020 (4)	0.7236 (2)	0.87388 (17)	0.0374 (7)
H16	−0.1141	0.6580	0.8796	0.045*
C17	−0.2159 (4)	0.7728 (2)	0.83219 (19)	0.0432 (8)
H17	−0.3071	0.7409	0.8103	0.052*
C18	−0.1993 (4)	0.8682 (2)	0.82167 (17)	0.0406 (7)
H18	−0.2781	0.9007	0.7918	0.049*
C19	−0.0683 (4)	0.9176 (2)	0.85429 (16)	0.0335 (7)
C20	0.0419 (4)	0.8665 (2)	0.89897 (14)	0.0282 (6)
C21	0.1642 (4)	0.7162 (2)	0.95050 (17)	0.0364 (7)
H21	0.1917	0.7540	0.9961	0.044*
C22	0.3218 (5)	0.7091 (2)	0.9033 (2)	0.0461 (8)
H22A	0.3554	0.7716	0.8869	0.055*
H22B	0.3008	0.6698	0.8592	0.055*
H22C	0.4103	0.6812	0.9336	0.055*
C23	0.1115 (6)	0.6197 (2)	0.9776 (2)	0.0545 (10)
H23A	0.1997	0.5926	1.0085	0.065*
H23B	0.0906	0.5793	0.9342	0.065*
H23C	0.0103	0.6252	1.0076	0.065*
C24	−0.0519 (4)	1.0221 (2)	0.84131 (18)	0.0396 (8)
H24	0.0658	1.0392	0.8521	0.048*
C25	−0.1593 (5)	1.0765 (2)	0.8963 (3)	0.0586 (10)
H25A	−0.1315	1.0581	0.9478	0.070*
H25B	−0.2761	1.0628	0.8865	0.070*
H25C	−0.1394	1.1436	0.8899	0.070*
C26	−0.0872 (5)	1.0502 (3)	0.7602 (2)	0.0623 (11)
H26A	−0.2043	1.0392	0.7488	0.075*
H26B	−0.0183	1.0129	0.7262	0.075*
H26C	−0.0618	1.1167	0.7534	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0354 (14)	0.0255 (12)	0.0303 (12)	0.0015 (11)	−0.0040 (11)	−0.0019 (10)
C1	0.0340 (16)	0.0248 (14)	0.0322 (14)	−0.0013 (14)	−0.0016 (13)	−0.0040 (12)
C2	0.0334 (15)	0.0293 (15)	0.0291 (13)	0.0027 (13)	−0.0018 (13)	0.0026 (13)
C3	0.0431 (17)	0.0271 (13)	0.0387 (15)	−0.0057 (15)	−0.0027 (15)	−0.0019 (13)
C4	0.0489 (18)	0.0383 (16)	0.0391 (16)	−0.0007 (17)	0.0021 (16)	0.0087 (14)
C5	0.0473 (19)	0.0491 (18)	0.0279 (14)	0.0042 (17)	−0.0023 (15)	0.0052 (14)
C6	0.0512 (18)	0.0367 (16)	0.0347 (15)	−0.0019 (17)	−0.0147 (15)	−0.0037 (13)
C7	0.0391 (16)	0.0298 (14)	0.0329 (15)	−0.0042 (15)	−0.0033 (13)	0.0013 (12)
C8	0.0297 (14)	0.0254 (13)	0.0315 (14)	0.0021 (13)	−0.0019 (13)	−0.0005 (11)
C9	0.0502 (19)	0.0352 (16)	0.0358 (16)	−0.0024 (16)	−0.0036 (16)	0.0020 (13)
C10	0.065 (2)	0.0340 (16)	0.0491 (19)	−0.0055 (18)	−0.0197 (19)	0.0057 (15)
C11	0.079 (3)	0.059 (2)	0.0328 (17)	−0.040 (2)	−0.0121 (19)	0.0129 (17)
C12	0.067 (2)	0.063 (2)	0.0333 (17)	−0.031 (2)	−0.0003 (18)	−0.0005 (16)
C13	0.0444 (18)	0.0420 (16)	0.0360 (15)	−0.0120 (16)	0.0041 (14)	−0.0062 (15)
C14	0.0365 (15)	0.0316 (14)	0.0260 (13)	−0.0075 (15)	−0.0038 (12)	−0.0018 (12)
C15	0.0369 (16)	0.0290 (14)	0.0242 (13)	0.0021 (13)	−0.0013 (14)	−0.0039 (12)
C16	0.0438 (18)	0.0333 (15)	0.0351 (15)	−0.0013 (15)	−0.0010 (15)	−0.0049 (14)
C17	0.0385 (18)	0.0483 (18)	0.0427 (17)	−0.0083 (16)	−0.0062 (16)	−0.0083 (16)
C18	0.0399 (17)	0.0486 (18)	0.0334 (15)	0.0025 (17)	−0.0105 (14)	−0.0015 (14)
C19	0.0338 (16)	0.0365 (16)	0.0303 (14)	0.0024 (14)	0.0029 (13)	−0.0040 (13)
C20	0.0319 (14)	0.0284 (13)	0.0242 (13)	0.0035 (13)	0.0007 (12)	−0.0048 (11)
C21	0.0454 (18)	0.0283 (14)	0.0354 (15)	0.0048 (14)	−0.0075 (15)	−0.0029 (13)
C22	0.0431 (18)	0.0409 (17)	0.054 (2)	0.0099 (16)	−0.0056 (17)	−0.0066 (16)
C23	0.065 (2)	0.0357 (17)	0.063 (2)	0.0021 (19)	−0.015 (2)	0.0084 (17)
C24	0.0386 (17)	0.0363 (16)	0.0438 (17)	0.0075 (15)	−0.0028 (15)	0.0061 (14)
C25	0.055 (2)	0.0350 (17)	0.086 (3)	0.0103 (18)	0.011 (2)	−0.0023 (19)
C26	0.060 (2)	0.064 (2)	0.064 (2)	0.000 (2)	−0.010 (2)	0.030 (2)

Geometric parameters (Å, º) top

N1—C2	1.218 (4)	C15—C20	1.406 (4)
N1—C20	1.428 (4)	C15—C21	1.523 (4)
C1—C2	1.328 (4)	C16—C17	1.376 (5)
C1—C14	1.490 (4)	C16—H16	0.9500
C1—C8	1.489 (4)	C17—C18	1.385 (5)
C3—C8	1.393 (4)	C17—H17	0.9500
C3—C4	1.383 (4)	C18—C19	1.399 (5)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.384 (5)	C19—C20	1.400 (4)
C4—H4	0.9500	C19—C24	1.519 (4)
C5—C6	1.374 (5)	C21—C23	1.523 (5)
C5—H5	0.9500	C21—C22	1.529 (5)
C6—C7	1.381 (4)	C21—H21	1.0000
C6—H6	0.9500	C22—H22A	0.9800
C7—C8	1.395 (4)	C22—H22B	0.9800
C7—H7	0.9500	C22—H22C	0.9800
C9—C10	1.385 (5)	C23—H23A	0.9800
C9—C14	1.393 (5)	C23—H23B	0.9800
C9—H9	0.9500	C23—H23C	0.9800
C10—C11	1.380 (6)	C24—C26	1.525 (5)
C10—H10	0.9500	C24—C25	1.521 (5)
C11—C12	1.379 (6)	C24—H24	1.0000
C11—H11	0.9500	C25—H25A	0.9800
C12—C13	1.381 (5)	C25—H25B	0.9800
C12—H12	0.9500	C25—H25C	0.9800
C13—C14	1.395 (4)	C26—H26A	0.9800
C13—H13	0.9500	C26—H26B	0.9800
C15—C16	1.388 (5)	C26—H26C	0.9800

C2—N1—C20	129.6 (3)	C16—C17—H17	119.6
C2—C1—C14	116.9 (3)	C18—C17—H17	119.6
C2—C1—C8	120.5 (3)	C17—C18—C19	121.0 (3)
C14—C1—C8	122.5 (2)	C17—C18—H18	119.5
N1—C2—C1	172.5 (3)	C19—C18—H18	119.5
C8—C3—C4	121.1 (3)	C18—C19—C20	117.0 (3)
C8—C3—H3	119.5	C18—C19—C24	120.0 (3)
C4—C3—H3	119.5	C20—C19—C24	123.0 (3)
C5—C4—C3	120.2 (3)	C15—C20—C19	122.6 (3)
C5—C4—H4	119.9	C15—C20—N1	115.4 (2)
C3—C4—H4	119.9	C19—C20—N1	121.9 (3)
C6—C5—C4	119.1 (3)	C23—C21—C15	114.2 (3)
C6—C5—H5	120.4	C23—C21—C22	110.3 (3)
C4—C5—H5	120.4	C15—C21—C22	110.4 (3)
C5—C6—C7	121.3 (3)	C23—C21—H21	107.2
C5—C6—H6	119.4	C15—C21—H21	107.2
C7—C6—H6	119.4	C22—C21—H21	107.2
C6—C7—C8	120.2 (3)	C21—C22—H22A	109.5
C6—C7—H7	119.9	C21—C22—H22B	109.5
C8—C7—H7	119.9	H22A—C22—H22B	109.5
C3—C8—C7	118.1 (3)	C21—C22—H22C	109.5
C3—C8—C1	120.9 (3)	H22A—C22—H22C	109.5
C7—C8—C1	120.9 (3)	H22B—C22—H22C	109.5
C10—C9—C14	119.5 (3)	C21—C23—H23A	109.5
C10—C9—H9	120.3	C21—C23—H23B	109.5
C14—C9—H9	120.3	H23A—C23—H23B	109.5
C11—C10—C9	121.0 (3)	C21—C23—H23C	109.5
C11—C10—H10	119.5	H23A—C23—H23C	109.5
C9—C10—H10	119.5	H23B—C23—H23C	109.5
C12—C11—C10	119.5 (3)	C19—C24—C26	112.8 (3)
C12—C11—H11	120.2	C19—C24—C25	110.8 (3)
C10—C11—H11	120.2	C26—C24—C25	111.5 (3)
C13—C12—C11	120.4 (3)	C19—C24—H24	107.1
C13—C12—H12	119.8	C26—C24—H24	107.1
C11—C12—H12	119.8	C25—C24—H24	107.1
C12—C13—C14	120.3 (3)	C24—C25—H25A	109.5
C12—C13—H13	119.9	C24—C25—H25B	109.5
C14—C13—H13	119.9	H25A—C25—H25B	109.5
C9—C14—C13	119.3 (3)	C24—C25—H25C	109.5
C9—C14—C1	121.4 (3)	H25A—C25—H25C	109.5
C13—C14—C1	119.2 (3)	H25B—C25—H25C	109.5
C16—C15—C20	117.8 (3)	C24—C26—H26A	109.5
C16—C15—C21	122.1 (3)	C24—C26—H26B	109.5
C20—C15—C21	120.0 (3)	H26A—C26—H26B	109.5
C17—C16—C15	120.7 (3)	C24—C26—H26C	109.5
C17—C16—H16	119.7	H26A—C26—H26C	109.5
C15—C16—H16	119.7	H26B—C26—H26C	109.5
C16—C17—C18	120.8 (3)

C20—N1—C2—C1	−169 (2)	C8—C1—C14—C13	137.9 (3)
C14—C1—C2—N1	82 (2)	C20—C15—C16—C17	1.3 (4)
C8—C1—C2—N1	−101 (2)	C21—C15—C16—C17	−176.5 (3)
C8—C3—C4—C5	0.5 (5)	C15—C16—C17—C18	1.3 (5)
C3—C4—C5—C6	−1.4 (5)	C16—C17—C18—C19	−1.3 (5)
C4—C5—C6—C7	1.0 (5)	C17—C18—C19—C20	−1.3 (5)
C5—C6—C7—C8	0.3 (5)	C17—C18—C19—C24	179.4 (3)
C4—C3—C8—C7	0.8 (5)	C16—C15—C20—C19	−4.1 (4)
C4—C3—C8—C1	179.7 (3)	C21—C15—C20—C19	173.8 (3)
C6—C7—C8—C3	−1.2 (4)	C16—C15—C20—N1	−179.8 (2)
C6—C7—C8—C1	179.9 (3)	C21—C15—C20—N1	−1.9 (4)
C2—C1—C8—C3	−18.4 (5)	C18—C19—C20—C15	4.0 (4)
C14—C1—C8—C3	158.0 (3)	C24—C19—C20—C15	−176.7 (3)
C2—C1—C8—C7	160.5 (3)	C18—C19—C20—N1	179.5 (3)
C14—C1—C8—C7	−23.1 (4)	C24—C19—C20—N1	−1.3 (4)
C14—C9—C10—C11	0.7 (5)	C2—N1—C20—C15	−139.4 (3)
C9—C10—C11—C12	0.1 (5)	C2—N1—C20—C19	44.9 (4)
C10—C11—C12—C13	−0.7 (6)	C16—C15—C21—C23	−21.2 (4)
C11—C12—C13—C14	0.6 (5)	C20—C15—C21—C23	161.0 (3)
C10—C9—C14—C13	−0.7 (5)	C16—C15—C21—C22	103.7 (3)
C10—C9—C14—C1	−178.5 (3)	C20—C15—C21—C22	−74.0 (3)
C12—C13—C14—C9	0.1 (5)	C18—C19—C24—C26	−41.8 (4)
C12—C13—C14—C1	178.0 (3)	C20—C19—C24—C26	139.0 (3)
C2—C1—C14—C9	132.2 (3)	C18—C19—C24—C25	84.0 (4)
C8—C1—C14—C9	−44.3 (4)	C20—C19—C24—C25	−95.2 (4)
C2—C1—C14—C13	−45.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱ	0.95	2.72	3.554 (4)	146

Symmetry code: (i) −x+1/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₇N
M_r	353.49
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	8.082 (4), 14.308 (4), 17.790 (2)
V (Å³)	2057 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3554, 1853, 1531
R_int	0.065
θ_max (°)	24.0
(sin θ/λ)_max (Å⁻¹)	0.572

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 0.82
No. of reflections	1853
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), SET4 (Boer et al., 1984), MolEN (Enraf–Nonius, 1990), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1990).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱ	0.95	2.72	3.554 (4)	146

Symmetry code: (i) −x+1/2, −y+2, z+1/2.

References

Boer, J. L. de & Duisenberg, A. J. M. (1984). Acta Cryst. A40, C410. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond, pp. 29–121. Oxford University Press. Google Scholar
Enraf–Nonius (1990). MolEN. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Imhof, W. (1997a). J. Organomet. Chem. 533, 31–43. CSD CrossRef CAS Web of Science Google Scholar
Imhof, W. (1997b). J. Organomet. Chem. 541, 109–116. CSD CrossRef CAS Web of Science Google Scholar
Jochims, J. C., Lambrecht, J., Burkert, U., Zsolnai, L. & Huttner, G. (1984). Tetrahedron, 40, 893–903. CSD CrossRef CAS Web of Science Google Scholar
Kuipers, W., Kanters, J. A. & Schouten, A. (1989). Acta Cryst. C45, 482–485. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Naqvi, R. R. & Wheatley, P. J. (1970). J. Chem. Soc. A, pp. 2053–2058. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1990). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Stevens, C. L. & Singhal, G. H. (1964). J. Org. Chem. 29, 34–37. CrossRef CAS Web of Science Google Scholar

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