5bα,6,7,13bα,14,15-Hexahydro­acridino[4,3-c]acridine

Ashmore, J.; Bishop, R.; Craig, D.C.; Scudder, M.L.

doi:10.1107/S1600536808014803

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1136

doi:10.1107/S1600536808014803

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5bα,6,7,13bα,14,15-Hexahydroacridino[4,3-c]acridine

Jason Ashmore,^a Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 3 May 2008; accepted 16 May 2008; online 21 May 2008)

The racemic title compound, C₂₄H₂₀N₂, gives spontaneous resolution with the formation of conglomerate crystals in the space group P2₁2₁2₁ when crystallized from ethyl acetate. The twisted molecules pack in parallel regions (ab plane) which then form a herringbone pattern along c.

Related literature

Condensation of two equivalents of 2-aminobenzaldehyde with one of cis-bicyclo[4.4.0]decane-2,7-dione affords the title compound by means of Friedländer condensation (Cheng & Yan, 1982 ). Substituted derivatives of molecules of this general V-shaped type frequently show inclusion properties (Bishop, 2006 ). For related literature, see: Collet et al. (1980 ); Jacques et al. (1981 ); Marjo et al. (1997 ); Peet & Cargill (1973 ); Smith & Opie (1955 ).

Experimental

Crystal data

C₂₄H₂₀N₂
M_r = 336.4
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.863 (3) Å
b = 9.759 (4) Å
c = 20.071 (8) Å
V = 1736 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 K
0.29 × 0.27 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1100 measured reflections
1100 independent reflections
737 reflections with I > 2σ(I)
θ_max = 21°
1 standard reflection frequency: 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.059
S = 1.64
1100 reflections
94 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: CAD-4 Manual (Schagen et al., 1989 ); cell refinement: CAD-4 Manual; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: RAELS (Rae, 2000 ); molecular graphics: ORTEPII (Johnson, 1976 ) and CrystalMaker (CrystalMaker, 2005 ); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014803/bq2079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014803/bq2079Isup2.hkl

checkCIF report

Comment top

The title compound was prepared as racemic material by Friedländer condensation (Cheng & Yan, 1982), but the crystallization process resulted in self-resolution and formation of a conglomerate (Collet et al., 1980; Jacques et al., 1981) (Fig 1). The two aromatic extremities of the molecule are essentially planar but are not coplanar, instead they exhibit a relative twist with the angle between the normals to the planes of 29.5 (2)°. These awkwardly shaped molecules pack in parallel regions in the ab plane. These regions then interact in herringbone fashion along c (Fig 2). Within the ab plane, molecules take part in edge-face aromatic interactions with H···π distance of about 3.4 Å. Because of the twisted nature of the molecule, it is not possible for them to take part in edge-edge C—H···N interactions that we have previously observed (Marjo et al., 1997). The crystals do not exhibit solvent inclusion, in contrast to other derivatives, which are V-shaped (Bishop, 2006).

Related literature top

Condensation of two equivalents of 2-aminobenzaldehyde with one of cis-bicyclo[4.4.0]decane-2,7-dione affords the title compound by means of Friedländer condensation (Cheng & Yan, 1982). Substituted derivatives of molecules of this general V-shaped type frequently show inclusion properties (Bishop, 2006). For related literature, see: Collet et al. (1980); Jacques et al. (1981); Marjo et al. (1997); Peet & Cargill (1973); Smith & Opie (1955).

Experimental top

Racemic cis-bicyclo[4.4.0]decane-2,7-dione (Peet & Cargill, 1973) (0.54 g, 3.25 mmol) and 2-aminobenzaldehyde (Smith & Opie, 1955) (0.88 g, 7.26 mmol) were dissolved in methanol (15 mL) with heating. To the cooled solution was added sodium hydroxide solution (2M; 2.5 mL) and the mixture stirred at rt for 2 days. The solid precipitate was filtered, and then recrystallised from ethyl acetate to yield the title compound (0.63 g, 58%) as pale yellow plates. ¹³C NMR (75.5 MHz, CDCl₃) δ: 27.9 (CH₂), 29.5 (CH₂), 42.7 (CH), 126.2 (CH), 127.3 (CH), 127.6 (C), 128.7 (CH), 128.9 (CH), 130.4 (C), 135.6 (CH), 147.5 (C), 161.4 (C); ¹H NMR (300 MHz, CDCl₃) δ: 2.09-2.23 (m, 2H), 2.45-2.50 (m, 2H), 3.07-3.16 (m, 2H), 3.23-3.34 (m, 2H), 3.70 (d, J = 9.6 Hz, 2H), 7.44-7.49 (m, 2H), 7.61-7.65 (m, 2H), 7.74 (d, J = 8.3 Hz, 2H), 7.86-7.90 (m, 2H), 8.05 (d, J = 8.7 Hz, 2H). X-ray quality crystals were obtained from ethyl acetate solution. The identical product is obtained if trans-bicyclo[4.4.0]decane-2,7-dione is used but the reaction takes longer.

Computing details top

Data collection: CAD-4 Manual (Schagen et al., 1989); cell refinement: CAD-4 Manual (Schagen et al., 1989); data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker, 2005); software used to prepare material for publication: local programs.

Figures top

	Fig. 1. Molecular structure of the compound, with ellipsoids drawn at 30% probability level.
	Fig. 2. Cell diagram showing the parallel regions (in the ab plane) which pack in a herringbone pattern.

5bα,6,7,13bα,14,15-Hexahydroacridino[4,3-c]acridine top

Crystal data top

C₂₄H₂₀N₂	D_x = 1.29 Mg m⁻³
M_r = 336.4	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 11 reflections
a = 8.863 (3) Å	θ = 10–11°
b = 9.759 (4) Å	µ = 0.08 mm⁻¹
c = 20.071 (8) Å	T = 294 K
V = 1736 (1) Å³	Plate, colourless
Z = 4	0.29 × 0.27 × 0.03 mm
F(000) = 712.0

Data collection top

Enraf–Nonius CAD-4 diffractometer	h = 0→8
ω–2θ scans	k = 0→9
1100 measured reflections	l = 0→20
1100 independent reflections	1 standard reflections every 30 min
737 reflections with I > 2σ(I)	intensity decay: none
θ_max = 21°

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F) + 0.0004F²]
S = 1.64	(Δ/σ)_max = 0.001
1100 reflections	Δρ_max = 0.26 e Å⁻³
94 parameters	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₄H₂₀N₂	V = 1736 (1) Å³
M_r = 336.4	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.863 (3) Å	µ = 0.08 mm⁻¹
b = 9.759 (4) Å	T = 294 K
c = 20.071 (8) Å	0.29 × 0.27 × 0.03 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 21°
1100 measured reflections	1 standard reflections every 30 min
1100 independent reflections	intensity decay: none
737 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.64	Δρ_max = 0.26 e Å⁻³
1100 reflections	Δρ_min = −0.42 e Å⁻³
94 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	−0.2254 (5)	0.4393 (4)	0.4278 (2)	0.0464 (9)
N2	0.2369 (5)	0.5930 (4)	0.2179 (2)	0.0470 (7)
C1	−0.0205 (6)	0.4796 (5)	0.3538 (3)	0.0427 (9)
C2	−0.1687 (6)	0.5253 (6)	0.3840 (3)	0.0442 (8)
C3	−0.2383 (6)	0.6509 (6)	0.3667 (3)	0.0517 (6)
C4	−0.1694 (6)	0.7391 (5)	0.3130 (3)	0.060 (1)
C5	0.0008 (6)	0.7137 (5)	0.3058 (3)	0.0535 (6)
C6	0.0323 (6)	0.5681 (5)	0.2944 (3)	0.0438 (8)
C7	0.1968 (6)	0.5402 (5)	0.2756 (3)	0.0435 (8)
C8	0.2927 (6)	0.4617 (6)	0.3160 (3)	0.0478 (8)
C9	0.2386 (7)	0.3999 (6)	0.3811 (3)	0.055 (1)
C10	0.0995 (6)	0.4728 (6)	0.4075 (2)	0.0500 (9)
C11	−0.3538 (6)	0.4784 (6)	0.4617 (3)	0.0491 (9)
C12	−0.4120 (7)	0.3867 (6)	0.5090 (3)	0.055 (1)
C13	−0.5368 (6)	0.4207 (6)	0.5461 (3)	0.059 (1)
C14	−0.6080 (7)	0.5469 (6)	0.5353 (3)	0.061 (1)
C15	−0.5551 (7)	0.6374 (6)	0.4883 (3)	0.062 (1)
C16	−0.4254 (7)	0.6036 (5)	0.4505 (3)	0.0541 (7)
C17	−0.3670 (7)	0.6883 (6)	0.4001 (3)	0.0587 (9)
C18	0.3795 (6)	0.5649 (5)	0.1950 (3)	0.0481 (7)
C19	0.4207 (7)	0.6142 (6)	0.1309 (3)	0.0553 (9)
C20	0.5578 (7)	0.5824 (6)	0.1045 (3)	0.058 (1)
C21	0.6593 (6)	0.4985 (6)	0.1403 (3)	0.057 (1)
C22	0.6250 (7)	0.4515 (6)	0.2028 (3)	0.057 (1)
C23	0.4821 (6)	0.4854 (6)	0.2310 (3)	0.0502 (8)
C24	0.4353 (6)	0.4356 (6)	0.2941 (3)	0.053 (1)
HC1	−0.0355	0.3843	0.3367	0.045
H1C4	−0.1862	0.8376	0.3246	0.074
H2C4	−0.2198	0.7180	0.2696	0.065
H1C5	0.0530	0.7439	0.3474	0.057
H2C5	0.0397	0.7679	0.2671	0.061
HC6	−0.0302	0.5398	0.2553	0.047
H1C9	0.3212	0.4072	0.4149	0.066
H2C9	0.2136	0.3011	0.3736	0.060
H1C10	0.1275	0.5679	0.4214	0.054
H2C10	0.0591	0.4215	0.4468	0.056
HC12	−0.3622	0.2958	0.5159	0.062
HC13	−0.5765	0.3559	0.5804	0.066
HC14	−0.6987	0.5716	0.5624	0.067
HC15	−0.6080	0.7266	0.4808	0.073
HC17	−0.4193	0.7760	0.3886	0.072
HC19	0.3487	0.6726	0.1051	0.064
HC20	0.5867	0.6184	0.0596	0.065
HC21	0.7581	0.4731	0.1197	0.062
HC22	0.6988	0.3943	0.2282	0.066
HC24	0.5066	0.3815	0.3224	0.065

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0488 (6)	0.048 (1)	0.0427 (8)	0.0013 (6)	0.0019 (6)	0.0061 (6)
N2	0.0502 (7)	0.047 (1)	0.0444 (9)	0.0024 (6)	0.0029 (7)	0.0088 (7)
C1	0.0464 (7)	0.041 (1)	0.0409 (9)	0.0038 (7)	0.0000 (6)	0.0070 (8)
C2	0.0470 (7)	0.043 (1)	0.0429 (9)	0.0032 (6)	0.0012 (7)	0.0052 (7)
C3	0.0523 (7)	0.0458 (8)	0.057 (1)	0.0085 (8)	0.0076 (7)	0.0085 (9)
C4	0.061 (1)	0.049 (1)	0.072 (2)	0.015 (1)	0.015 (1)	0.019 (2)
C5	0.058 (1)	0.0405 (9)	0.062 (1)	0.0067 (8)	0.0120 (9)	0.0108 (9)
C6	0.0476 (7)	0.041 (1)	0.0431 (9)	0.0047 (7)	0.0011 (7)	0.0084 (8)
C7	0.0470 (7)	0.042 (1)	0.0418 (9)	0.0028 (6)	0.0007 (7)	0.0061 (7)
C8	0.0464 (7)	0.053 (1)	0.0440 (8)	0.0058 (6)	0.0002 (6)	0.0085 (7)
C9	0.0490 (7)	0.068 (2)	0.0476 (9)	0.0108 (8)	0.0007 (7)	0.0178 (8)
C10	0.0475 (7)	0.061 (2)	0.041 (1)	0.0037 (7)	−0.0006 (7)	0.0095 (7)
C11	0.0493 (7)	0.054 (1)	0.0445 (9)	−0.0010 (6)	0.0033 (6)	0.0019 (6)
C12	0.0547 (9)	0.064 (2)	0.047 (1)	−0.0039 (9)	0.0065 (9)	0.0055 (8)
C13	0.055 (1)	0.074 (2)	0.049 (1)	−0.008 (1)	0.008 (1)	−0.001 (1)
C14	0.053 (1)	0.073 (2)	0.056 (2)	−0.006 (1)	0.010 (1)	−0.010 (1)
C15	0.055 (1)	0.065 (2)	0.067 (2)	0.002 (1)	0.014 (1)	−0.005 (1)
C16	0.0513 (8)	0.0549 (9)	0.056 (1)	0.0030 (8)	0.0080 (8)	−0.0006 (9)
C17	0.0559 (9)	0.0520 (9)	0.068 (2)	0.011 (1)	0.013 (1)	0.007 (1)
C18	0.0497 (7)	0.050 (1)	0.0442 (9)	−0.0004 (6)	0.0032 (7)	0.0044 (6)
C19	0.055 (1)	0.064 (2)	0.047 (1)	−0.0023 (9)	0.006 (1)	0.009 (1)
C20	0.055 (1)	0.070 (2)	0.048 (1)	−0.007 (1)	0.007 (1)	0.001 (1)
C21	0.0507 (8)	0.068 (2)	0.052 (1)	−0.0038 (8)	0.0070 (9)	−0.005 (1)
C22	0.0484 (7)	0.068 (2)	0.054 (1)	0.0035 (7)	0.0051 (7)	0.001 (1)
C23	0.0473 (7)	0.056 (1)	0.0470 (8)	0.0025 (6)	0.0025 (6)	0.0027 (7)
C24	0.0471 (7)	0.064 (2)	0.0490 (8)	0.0082 (6)	0.0015 (6)	0.0097 (7)

Geometric parameters (Å, º) top

N1—C2	1.316 (6)	C10—H2C10	1.000
N1—C11	1.378 (6)	C11—C12	1.404 (7)
N2—C7	1.316 (6)	C11—C16	1.395 (7)
N2—C18	1.373 (6)	C12—C13	1.373 (7)
C1—C2	1.514 (7)	C12—HC12	1.000
C1—C6	1.544 (7)	C13—C14	1.400 (8)
C1—C10	1.516 (6)	C13—HC13	1.000
C1—HC1	1.000	C14—C15	1.376 (7)
C2—C3	1.415 (7)	C14—HC14	1.000
C3—C4	1.508 (7)	C15—C16	1.417 (7)
C3—C17	1.373 (7)	C15—HC15	1.000
C4—C5	1.536 (7)	C16—C17	1.405 (7)
C4—H1C4	1.000	C17—HC17	1.000
C4—H2C4	1.000	C18—C19	1.422 (7)
C5—C6	1.466 (7)	C18—C23	1.397 (7)
C5—H1C5	1.000	C19—C20	1.362 (7)
C5—H2C5	1.000	C19—HC19	1.000
C6—C7	1.531 (7)	C20—C21	1.413 (7)
C6—HC6	1.000	C20—HC20	1.000
C7—C8	1.403 (6)	C21—C22	1.370 (7)
C8—C9	1.517 (7)	C21—HC21	1.000
C8—C24	1.362 (7)	C22—C23	1.426 (7)
C9—C10	1.519 (8)	C22—HC22	1.000
C9—H1C9	1.000	C23—C24	1.418 (7)
C9—H2C9	1.000	C24—HC24	1.000
C10—H1C10	1.000

C2—N1—C11	117.9 (5)	C1—C10—H2C10	109.3
C7—N2—C18	117.7 (5)	C9—C10—H1C10	109.3
C2—C1—C6	114.0 (4)	C9—C10—H2C10	109.3
C2—C1—C10	109.7 (4)	H1C10—C10—H2C10	109.5
C2—C1—HC1	107.2	N1—C11—C12	117.4 (5)
C6—C1—C10	111.1 (4)	N1—C11—C16	122.5 (5)
C6—C1—HC1	107.2	C12—C11—C16	120.0 (5)
C10—C1—HC1	107.2	C11—C12—C13	120.5 (6)
N1—C2—C1	114.3 (5)	C11—C12—HC12	119.7
N1—C2—C3	123.3 (5)	C13—C12—HC12	119.7
C1—C2—C3	122.3 (5)	C12—C13—C14	119.5 (6)
C2—C3—C4	119.6 (5)	C12—C13—HC13	120.2
C2—C3—C17	118.2 (5)	C14—C13—HC13	120.2
C4—C3—C17	122.2 (5)	C13—C14—C15	121.1 (5)
C3—C4—C5	111.9 (5)	C13—C14—HC14	119.4
C3—C4—H1C4	108.8	C15—C14—HC14	119.4
C3—C4—H2C4	108.8	C14—C15—C16	119.6 (6)
C5—C4—H1C4	108.8	C14—C15—HC15	120.2
C5—C4—H2C4	108.8	C16—C15—HC15	120.2
H1C4—C4—H2C4	109.5	C11—C16—C15	119.1 (5)
C4—C5—C6	110.9 (5)	C11—C16—C17	117.7 (5)
C4—C5—H1C5	109.1	C15—C16—C17	123.2 (5)
C4—C5—H2C5	109.1	C3—C17—C16	120.1 (5)
C6—C5—H1C5	109.1	C3—C17—HC17	120.0
C6—C5—H2C5	109.1	C16—C17—HC17	120.0
H1C5—C5—H2C5	109.5	N2—C18—C19	118.1 (5)
C1—C6—C5	111.4 (5)	N2—C18—C23	122.5 (5)
C1—C6—C7	112.3 (4)	C19—C18—C23	119.3 (6)
C1—C6—HC6	106.5	C18—C19—C20	120.3 (6)
C5—C6—C7	113.0 (5)	C18—C19—HC19	119.8
C5—C6—HC6	106.5	C20—C19—HC19	119.8
C7—C6—HC6	106.5	C19—C20—C21	120.1 (5)
N2—C7—C6	113.9 (5)	C19—C20—HC20	119.9
N2—C7—C8	124.0 (5)	C21—C20—HC20	119.9
C6—C7—C8	122.1 (5)	C20—C21—C22	121.2 (6)
C7—C8—C9	121.6 (5)	C20—C21—HC21	119.4
C7—C8—C24	118.6 (5)	C22—C21—HC21	119.4
C9—C8—C24	119.8 (5)	C21—C22—C23	118.9 (6)
C8—C9—C10	111.8 (5)	C21—C22—HC22	120.5
C8—C9—H1C9	108.9	C23—C22—HC22	120.5
C8—C9—H2C9	108.9	C18—C23—C22	120.1 (5)
C10—C9—H1C9	108.9	C18—C23—C24	117.5 (5)
C10—C9—H2C9	108.9	C22—C23—C24	122.4 (5)
H1C9—C9—H2C9	109.5	C8—C24—C23	119.7 (5)
C1—C10—C9	110.0 (4)	C8—C24—HC24	120.2
C1—C10—H1C10	109.3	C23—C24—HC24	120.2

C11—N1—C2—C1	174.9 (4)	C7—C8—C9—H1C9	−141.1
C11—N1—C2—C3	−4.6 (7)	C7—C8—C9—H2C9	99.6
C2—N1—C11—C12	−179.0 (5)	C24—C8—C9—C10	162.6 (5)
C2—N1—C11—C16	0.9 (7)	C24—C8—C9—H1C9	42.3
C18—N2—C7—C6	−175.6 (4)	C24—C8—C9—H2C9	−77.1
C18—N2—C7—C8	2.6 (7)	C7—C8—C24—C23	−1.2 (8)
C7—N2—C18—C19	176.1 (5)	C7—C8—C24—HC24	178.8
C7—N2—C18—C23	−1.1 (7)	C9—C8—C24—C23	175.6 (5)
C6—C1—C2—N1	170.4 (4)	C9—C8—C24—HC24	−4.4
C6—C1—C2—C3	−10.1 (7)	C8—C9—C10—C1	52.2 (6)
C10—C1—C2—N1	−64.2 (6)	C8—C9—C10—H1C10	−67.9
C10—C1—C2—C3	115.2 (6)	C8—C9—C10—H2C10	172.3
HC1—C1—C2—N1	51.9	H1C9—C9—C10—C1	172.6
HC1—C1—C2—C3	−128.6	H1C9—C9—C10—H1C10	52.5
C2—C1—C6—C5	38.9 (6)	H1C9—C9—C10—H2C10	−67.4
C2—C1—C6—C7	166.9 (4)	H2C9—C9—C10—C1	−68.1
C2—C1—C6—HC6	−76.8	H2C9—C9—C10—H1C10	171.8
C10—C1—C6—C5	−85.6 (6)	H2C9—C9—C10—H2C10	52.0
C10—C1—C6—C7	42.4 (6)	N1—C11—C12—C13	178.0 (5)
C10—C1—C6—HC6	158.6	N1—C11—C12—HC12	−2.0
HC1—C1—C6—C5	157.5	C16—C11—C12—C13	−1.9 (8)
HC1—C1—C6—C7	−74.5	C16—C11—C12—HC12	178.1
HC1—C1—C6—HC6	41.7	N1—C11—C16—C15	−178.7 (5)
C2—C1—C10—C9	168.5 (5)	N1—C11—C16—C17	3.4 (8)
C2—C1—C10—H1C10	−71.5	C12—C11—C16—C15	1.2 (8)
C2—C1—C10—H2C10	48.4	C12—C11—C16—C17	−176.7 (5)
C6—C1—C10—C9	−64.6 (6)	C11—C12—C13—C14	1.3 (8)
C6—C1—C10—H1C10	55.5	C11—C12—C13—HC13	−178.7
C6—C1—C10—H2C10	175.3	HC12—C12—C13—C14	−178.7
HC1—C1—C10—C9	52.3	HC12—C12—C13—HC13	1.3
HC1—C1—C10—H1C10	172.4	C12—C13—C14—C15	0.1 (9)
HC1—C1—C10—H2C10	−67.7	C12—C13—C14—HC14	−179.9
N1—C2—C3—C4	−176.5 (5)	HC13—C13—C14—C15	−179.9
N1—C2—C3—C17	3.9 (8)	HC13—C13—C14—HC14	0.1
C1—C2—C3—C4	4.1 (8)	C13—C14—C15—C16	−0.8 (9)
C1—C2—C3—C17	−175.5 (5)	C13—C14—C15—HC15	179.2
C2—C3—C4—C5	−25.4 (7)	HC14—C14—C15—C16	179.2
C2—C3—C4—H1C4	−145.7	HC14—C14—C15—HC15	−0.8
C2—C3—C4—H2C4	95.0	C14—C15—C16—C11	0.2 (8)
C17—C3—C4—C5	154.2 (6)	C14—C15—C16—C17	178.0 (5)
C17—C3—C4—H1C4	33.8	HC15—C15—C16—C11	−179.8
C17—C3—C4—H2C4	−85.5	HC15—C15—C16—C17	−2.0
C2—C3—C17—C16	0.6 (8)	C11—C16—C17—C3	−4.0 (8)
C2—C3—C17—HC17	−179.4	C11—C16—C17—HC17	176.0
C4—C3—C17—C16	−179.0 (5)	C15—C16—C17—C3	178.2 (6)
C4—C3—C17—HC17	1.0	C15—C16—C17—HC17	−1.8
C3—C4—C5—C6	54.8 (7)	N2—C18—C19—C20	−176.2 (5)
C3—C4—C5—H1C5	−65.5	N2—C18—C19—HC19	3.8
C3—C4—C5—H2C5	175.0	C23—C18—C19—C20	1.0 (9)
H1C4—C4—C5—C6	175.1	C23—C18—C19—HC19	−179.0
H1C4—C4—C5—H1C5	54.9	N2—C18—C23—C22	175.6 (5)
H1C4—C4—C5—H2C5	−64.6	N2—C18—C23—C24	−1.4 (8)
H2C4—C4—C5—C6	−65.6	C19—C18—C23—C22	−1.6 (8)
H2C4—C4—C5—H1C5	174.2	C19—C18—C23—C24	−178.5 (5)
H2C4—C4—C5—H2C5	54.6	C18—C19—C20—C21	0.8 (9)
C4—C5—C6—C1	−61.8 (6)	C18—C19—C20—HC20	−179.2
C4—C5—C6—C7	170.6 (5)	HC19—C19—C20—C21	−179.2
C4—C5—C6—HC6	54.0	HC19—C19—C20—HC20	0.8
H1C5—C5—C6—C1	58.5	C19—C20—C21—C22	−2.2 (9)
H1C5—C5—C6—C7	−69.2	C19—C20—C21—HC21	177.8
H1C5—C5—C6—HC6	174.2	HC20—C20—C21—C22	177.8
H2C5—C5—C6—C1	178.0	HC20—C20—C21—HC21	−2.2
H2C5—C5—C6—C7	50.4	C20—C21—C22—C23	1.6 (9)
H2C5—C5—C6—HC6	−66.2	C20—C21—C22—HC22	−178.4
C1—C6—C7—N2	167.5 (4)	HC21—C21—C22—C23	−178.4
C1—C6—C7—C8	−10.7 (7)	HC21—C21—C22—HC22	1.6
C5—C6—C7—N2	−65.3 (6)	C21—C22—C23—C18	0.3 (8)
C5—C6—C7—C8	116.4 (6)	C21—C22—C23—C24	177.0 (5)
HC6—C6—C7—N2	51.3	HC22—C22—C23—C18	−179.7
HC6—C6—C7—C8	−127.0	HC22—C22—C23—C24	−3.0
N2—C7—C8—C9	−178.1 (5)	C18—C23—C24—C8	2.5 (8)
N2—C7—C8—C24	−1.4 (8)	C18—C23—C24—HC24	−177.5
C6—C7—C8—C9	−0.1 (8)	C22—C23—C24—C8	−174.4 (5)
C6—C7—C8—C24	176.6 (5)	C22—C23—C24—HC24	5.6
C7—C8—C9—C10	−20.7 (7)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂
M_r	336.4
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	8.863 (3), 9.759 (4), 20.071 (8)
V (Å³)	1736 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.27 × 0.03

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1100, 1100, 737
R_int	?
θ_max (°)	21
(sin θ/λ)_max (Å⁻¹)	0.504

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.059, 1.64
No. of reflections	1100
No. of parameters	94
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.42

Computer programs: CAD-4 Manual (Schagen et al., 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker, 2005), local programs.

Acknowledgements

This research was supported by the UNSW Faculty Research Grants Program.

References

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