PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1136.
Published online 2008 May 21. doi:  10.1107/S1600536808014803
PMCID: PMC2961454

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

Abstract

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 [triangle]). Substituted derivatives of mol­ecules of this general V-shaped type frequently show inclusion properties (Bishop, 2006 [triangle]). For related literature, see: Collet et al. (1980 [triangle]); Jacques et al. (1981 [triangle]); Marjo et al. (1997 [triangle]); Peet & Cargill (1973 [triangle]); Smith & Opie (1955 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1136-scheme1.jpg

Experimental

Crystal data

  • C24H20N2
  • M r = 336.4
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1136-efi1.jpg
  • 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)
  • θmax = 21°
  • 1 standard reflection frequency: 30 min intensity decay: none

Refinement

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

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

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Hydrogen atoms attached to C were included at calculated positions (C—H = 1.0 Å) and were refined with isotropic thermal parameters equivalent to those of the atom to which they were bonded.

Figures

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.

Crystal data

C24H20N2Dx = 1.29 Mg m3
Mr = 336.4Mo Kα radiation λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 11 reflections
a = 8.863 (3) Åθ = 10–11º
b = 9.759 (4) ŵ = 0.08 mm1
c = 20.071 (8) ÅT = 294 K
V = 1736 (1) Å3Plate, colourless
Z = 40.29 × 0.27 × 0.03 mm
F000 = 712.0

Data collection

Enraf–Nonius CAD-4 diffractometerh = 0→8
ω–2θ scansk = 0→9
Absorption correction: nonel = 0→20
1100 measured reflections1 standard reflections
1100 independent reflections every 30 min
737 reflections with I > 2σ(I) intensity decay: none
θmax = 21º

Refinement

Refinement on FH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048  w = 1/[σ2(F) + 0.0004F2]
wR(F2) = 0.059(Δ/σ)max = 0.001
S = 1.64Δρmax = 0.26 e Å3
1100 reflectionsΔρmin = −0.42 e Å3
94 parametersExtinction correction: none

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

xyzUiso*/Ueq
N1−0.2254 (5)0.4393 (4)0.4278 (2)0.0464 (9)
N20.2369 (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)
C50.0008 (6)0.7137 (5)0.3058 (3)0.0535 (6)
C60.0323 (6)0.5681 (5)0.2944 (3)0.0438 (8)
C70.1968 (6)0.5402 (5)0.2756 (3)0.0435 (8)
C80.2927 (6)0.4617 (6)0.3160 (3)0.0478 (8)
C90.2386 (7)0.3999 (6)0.3811 (3)0.055 (1)
C100.0995 (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)
C180.3795 (6)0.5649 (5)0.1950 (3)0.0481 (7)
C190.4207 (7)0.6142 (6)0.1309 (3)0.0553 (9)
C200.5578 (7)0.5824 (6)0.1045 (3)0.058 (1)
C210.6593 (6)0.4985 (6)0.1403 (3)0.057 (1)
C220.6250 (7)0.4515 (6)0.2028 (3)0.057 (1)
C230.4821 (6)0.4854 (6)0.2310 (3)0.0502 (8)
C240.4353 (6)0.4356 (6)0.2941 (3)0.053 (1)
HC1−0.03550.38430.33670.045
H1C4−0.18620.83760.32460.074
H2C4−0.21980.71800.26960.065
H1C50.05300.74390.34740.057
H2C50.03970.76790.26710.061
HC6−0.03020.53980.25530.047
H1C90.32120.40720.41490.066
H2C90.21360.30110.37360.060
H1C100.12750.56790.42140.054
H2C100.05910.42150.44680.056
HC12−0.36220.29580.51590.062
HC13−0.57650.35590.58040.066
HC14−0.69870.57160.56240.067
HC15−0.60800.72660.48080.073
HC17−0.41930.77600.38860.072
HC190.34870.67260.10510.064
HC200.58670.61840.05960.065
HC210.75810.47310.11970.062
HC220.69880.39430.22820.066
HC240.50660.38150.32240.065

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0488 (6)0.048 (1)0.0427 (8)0.0013 (6)0.0019 (6)0.0061 (6)
N20.0502 (7)0.047 (1)0.0444 (9)0.0024 (6)0.0029 (7)0.0088 (7)
C10.0464 (7)0.041 (1)0.0409 (9)0.0038 (7)0.0000 (6)0.0070 (8)
C20.0470 (7)0.043 (1)0.0429 (9)0.0032 (6)0.0012 (7)0.0052 (7)
C30.0523 (7)0.0458 (8)0.057 (1)0.0085 (8)0.0076 (7)0.0085 (9)
C40.061 (1)0.049 (1)0.072 (2)0.015 (1)0.015 (1)0.019 (2)
C50.058 (1)0.0405 (9)0.062 (1)0.0067 (8)0.0120 (9)0.0108 (9)
C60.0476 (7)0.041 (1)0.0431 (9)0.0047 (7)0.0011 (7)0.0084 (8)
C70.0470 (7)0.042 (1)0.0418 (9)0.0028 (6)0.0007 (7)0.0061 (7)
C80.0464 (7)0.053 (1)0.0440 (8)0.0058 (6)0.0002 (6)0.0085 (7)
C90.0490 (7)0.068 (2)0.0476 (9)0.0108 (8)0.0007 (7)0.0178 (8)
C100.0475 (7)0.061 (2)0.041 (1)0.0037 (7)−0.0006 (7)0.0095 (7)
C110.0493 (7)0.054 (1)0.0445 (9)−0.0010 (6)0.0033 (6)0.0019 (6)
C120.0547 (9)0.064 (2)0.047 (1)−0.0039 (9)0.0065 (9)0.0055 (8)
C130.055 (1)0.074 (2)0.049 (1)−0.008 (1)0.008 (1)−0.001 (1)
C140.053 (1)0.073 (2)0.056 (2)−0.006 (1)0.010 (1)−0.010 (1)
C150.055 (1)0.065 (2)0.067 (2)0.002 (1)0.014 (1)−0.005 (1)
C160.0513 (8)0.0549 (9)0.056 (1)0.0030 (8)0.0080 (8)−0.0006 (9)
C170.0559 (9)0.0520 (9)0.068 (2)0.011 (1)0.013 (1)0.007 (1)
C180.0497 (7)0.050 (1)0.0442 (9)−0.0004 (6)0.0032 (7)0.0044 (6)
C190.055 (1)0.064 (2)0.047 (1)−0.0023 (9)0.006 (1)0.009 (1)
C200.055 (1)0.070 (2)0.048 (1)−0.007 (1)0.007 (1)0.001 (1)
C210.0507 (8)0.068 (2)0.052 (1)−0.0038 (8)0.0070 (9)−0.005 (1)
C220.0484 (7)0.068 (2)0.054 (1)0.0035 (7)0.0051 (7)0.001 (1)
C230.0473 (7)0.056 (1)0.0470 (8)0.0025 (6)0.0025 (6)0.0027 (7)
C240.0471 (7)0.064 (2)0.0490 (8)0.0082 (6)0.0015 (6)0.0097 (7)

Geometric parameters (Å, °)

N1—C21.316 (6)C10—H2C101.000
N1—C111.378 (6)C11—C121.404 (7)
N2—C71.316 (6)C11—C161.395 (7)
N2—C181.373 (6)C12—C131.373 (7)
C1—C21.514 (7)C12—HC121.000
C1—C61.544 (7)C13—C141.400 (8)
C1—C101.516 (6)C13—HC131.000
C1—HC11.000C14—C151.376 (7)
C2—C31.415 (7)C14—HC141.000
C3—C41.508 (7)C15—C161.417 (7)
C3—C171.373 (7)C15—HC151.000
C4—C51.536 (7)C16—C171.405 (7)
C4—H1C41.000C17—HC171.000
C4—H2C41.000C18—C191.422 (7)
C5—C61.466 (7)C18—C231.397 (7)
C5—H1C51.000C19—C201.362 (7)
C5—H2C51.000C19—HC191.000
C6—C71.531 (7)C20—C211.413 (7)
C6—HC61.000C20—HC201.000
C7—C81.403 (6)C21—C221.370 (7)
C8—C91.517 (7)C21—HC211.000
C8—C241.362 (7)C22—C231.426 (7)
C9—C101.519 (8)C22—HC221.000
C9—H1C91.000C23—C241.418 (7)
C9—H2C91.000C24—HC241.000
C10—H1C101.000
C2—N1—C11117.9 (5)C1—C10—H2C10109.3
C7—N2—C18117.7 (5)C9—C10—H1C10109.3
C2—C1—C6114.0 (4)C9—C10—H2C10109.3
C2—C1—C10109.7 (4)H1C10—C10—H2C10109.5
C2—C1—HC1107.2N1—C11—C12117.4 (5)
C6—C1—C10111.1 (4)N1—C11—C16122.5 (5)
C6—C1—HC1107.2C12—C11—C16120.0 (5)
C10—C1—HC1107.2C11—C12—C13120.5 (6)
N1—C2—C1114.3 (5)C11—C12—HC12119.7
N1—C2—C3123.3 (5)C13—C12—HC12119.7
C1—C2—C3122.3 (5)C12—C13—C14119.5 (6)
C2—C3—C4119.6 (5)C12—C13—HC13120.2
C2—C3—C17118.2 (5)C14—C13—HC13120.2
C4—C3—C17122.2 (5)C13—C14—C15121.1 (5)
C3—C4—C5111.9 (5)C13—C14—HC14119.4
C3—C4—H1C4108.8C15—C14—HC14119.4
C3—C4—H2C4108.8C14—C15—C16119.6 (6)
C5—C4—H1C4108.8C14—C15—HC15120.2
C5—C4—H2C4108.8C16—C15—HC15120.2
H1C4—C4—H2C4109.5C11—C16—C15119.1 (5)
C4—C5—C6110.9 (5)C11—C16—C17117.7 (5)
C4—C5—H1C5109.1C15—C16—C17123.2 (5)
C4—C5—H2C5109.1C3—C17—C16120.1 (5)
C6—C5—H1C5109.1C3—C17—HC17120.0
C6—C5—H2C5109.1C16—C17—HC17120.0
H1C5—C5—H2C5109.5N2—C18—C19118.1 (5)
C1—C6—C5111.4 (5)N2—C18—C23122.5 (5)
C1—C6—C7112.3 (4)C19—C18—C23119.3 (6)
C1—C6—HC6106.5C18—C19—C20120.3 (6)
C5—C6—C7113.0 (5)C18—C19—HC19119.8
C5—C6—HC6106.5C20—C19—HC19119.8
C7—C6—HC6106.5C19—C20—C21120.1 (5)
N2—C7—C6113.9 (5)C19—C20—HC20119.9
N2—C7—C8124.0 (5)C21—C20—HC20119.9
C6—C7—C8122.1 (5)C20—C21—C22121.2 (6)
C7—C8—C9121.6 (5)C20—C21—HC21119.4
C7—C8—C24118.6 (5)C22—C21—HC21119.4
C9—C8—C24119.8 (5)C21—C22—C23118.9 (6)
C8—C9—C10111.8 (5)C21—C22—HC22120.5
C8—C9—H1C9108.9C23—C22—HC22120.5
C8—C9—H2C9108.9C18—C23—C22120.1 (5)
C10—C9—H1C9108.9C18—C23—C24117.5 (5)
C10—C9—H2C9108.9C22—C23—C24122.4 (5)
H1C9—C9—H2C9109.5C8—C24—C23119.7 (5)
C1—C10—C9110.0 (4)C8—C24—HC24120.2
C1—C10—H1C10109.3C23—C24—HC24120.2
C11—N1—C2—C1174.9 (4)C7—C8—C9—H1C9−141.1
C11—N1—C2—C3−4.6 (7)C7—C8—C9—H2C999.6
C2—N1—C11—C12−179.0 (5)C24—C8—C9—C10162.6 (5)
C2—N1—C11—C160.9 (7)C24—C8—C9—H1C942.3
C18—N2—C7—C6−175.6 (4)C24—C8—C9—H2C9−77.1
C18—N2—C7—C82.6 (7)C7—C8—C24—C23−1.2 (8)
C7—N2—C18—C19176.1 (5)C7—C8—C24—HC24178.8
C7—N2—C18—C23−1.1 (7)C9—C8—C24—C23175.6 (5)
C6—C1—C2—N1170.4 (4)C9—C8—C24—HC24−4.4
C6—C1—C2—C3−10.1 (7)C8—C9—C10—C152.2 (6)
C10—C1—C2—N1−64.2 (6)C8—C9—C10—H1C10−67.9
C10—C1—C2—C3115.2 (6)C8—C9—C10—H2C10172.3
HC1—C1—C2—N151.9H1C9—C9—C10—C1172.6
HC1—C1—C2—C3−128.6H1C9—C9—C10—H1C1052.5
C2—C1—C6—C538.9 (6)H1C9—C9—C10—H2C10−67.4
C2—C1—C6—C7166.9 (4)H2C9—C9—C10—C1−68.1
C2—C1—C6—HC6−76.8H2C9—C9—C10—H1C10171.8
C10—C1—C6—C5−85.6 (6)H2C9—C9—C10—H2C1052.0
C10—C1—C6—C742.4 (6)N1—C11—C12—C13178.0 (5)
C10—C1—C6—HC6158.6N1—C11—C12—HC12−2.0
HC1—C1—C6—C5157.5C16—C11—C12—C13−1.9 (8)
HC1—C1—C6—C7−74.5C16—C11—C12—HC12178.1
HC1—C1—C6—HC641.7N1—C11—C16—C15−178.7 (5)
C2—C1—C10—C9168.5 (5)N1—C11—C16—C173.4 (8)
C2—C1—C10—H1C10−71.5C12—C11—C16—C151.2 (8)
C2—C1—C10—H2C1048.4C12—C11—C16—C17−176.7 (5)
C6—C1—C10—C9−64.6 (6)C11—C12—C13—C141.3 (8)
C6—C1—C10—H1C1055.5C11—C12—C13—HC13−178.7
C6—C1—C10—H2C10175.3HC12—C12—C13—C14−178.7
HC1—C1—C10—C952.3HC12—C12—C13—HC131.3
HC1—C1—C10—H1C10172.4C12—C13—C14—C150.1 (9)
HC1—C1—C10—H2C10−67.7C12—C13—C14—HC14−179.9
N1—C2—C3—C4−176.5 (5)HC13—C13—C14—C15−179.9
N1—C2—C3—C173.9 (8)HC13—C13—C14—HC140.1
C1—C2—C3—C44.1 (8)C13—C14—C15—C16−0.8 (9)
C1—C2—C3—C17−175.5 (5)C13—C14—C15—HC15179.2
C2—C3—C4—C5−25.4 (7)HC14—C14—C15—C16179.2
C2—C3—C4—H1C4−145.7HC14—C14—C15—HC15−0.8
C2—C3—C4—H2C495.0C14—C15—C16—C110.2 (8)
C17—C3—C4—C5154.2 (6)C14—C15—C16—C17178.0 (5)
C17—C3—C4—H1C433.8HC15—C15—C16—C11−179.8
C17—C3—C4—H2C4−85.5HC15—C15—C16—C17−2.0
C2—C3—C17—C160.6 (8)C11—C16—C17—C3−4.0 (8)
C2—C3—C17—HC17−179.4C11—C16—C17—HC17176.0
C4—C3—C17—C16−179.0 (5)C15—C16—C17—C3178.2 (6)
C4—C3—C17—HC171.0C15—C16—C17—HC17−1.8
C3—C4—C5—C654.8 (7)N2—C18—C19—C20−176.2 (5)
C3—C4—C5—H1C5−65.5N2—C18—C19—HC193.8
C3—C4—C5—H2C5175.0C23—C18—C19—C201.0 (9)
H1C4—C4—C5—C6175.1C23—C18—C19—HC19−179.0
H1C4—C4—C5—H1C554.9N2—C18—C23—C22175.6 (5)
H1C4—C4—C5—H2C5−64.6N2—C18—C23—C24−1.4 (8)
H2C4—C4—C5—C6−65.6C19—C18—C23—C22−1.6 (8)
H2C4—C4—C5—H1C5174.2C19—C18—C23—C24−178.5 (5)
H2C4—C4—C5—H2C554.6C18—C19—C20—C210.8 (9)
C4—C5—C6—C1−61.8 (6)C18—C19—C20—HC20−179.2
C4—C5—C6—C7170.6 (5)HC19—C19—C20—C21−179.2
C4—C5—C6—HC654.0HC19—C19—C20—HC200.8
H1C5—C5—C6—C158.5C19—C20—C21—C22−2.2 (9)
H1C5—C5—C6—C7−69.2C19—C20—C21—HC21177.8
H1C5—C5—C6—HC6174.2HC20—C20—C21—C22177.8
H2C5—C5—C6—C1178.0HC20—C20—C21—HC21−2.2
H2C5—C5—C6—C750.4C20—C21—C22—C231.6 (9)
H2C5—C5—C6—HC6−66.2C20—C21—C22—HC22−178.4
C1—C6—C7—N2167.5 (4)HC21—C21—C22—C23−178.4
C1—C6—C7—C8−10.7 (7)HC21—C21—C22—HC221.6
C5—C6—C7—N2−65.3 (6)C21—C22—C23—C180.3 (8)
C5—C6—C7—C8116.4 (6)C21—C22—C23—C24177.0 (5)
HC6—C6—C7—N251.3HC22—C22—C23—C18−179.7
HC6—C6—C7—C8−127.0HC22—C22—C23—C24−3.0
N2—C7—C8—C9−178.1 (5)C18—C23—C24—C82.5 (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—C24176.6 (5)C22—C23—C24—HC245.6
C7—C8—C9—C10−20.7 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2079).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Bishop, R. (2006). Crystal Engineering of Halogenated Heteroaromatic Clathrate Systems, in Frontiers in Crystal Engineering, edited by E. R. T. Tiekink & J. J. Vittal, ch. 5, pp. 91–116. Chichester: Wiley.
  • Cheng, C.-C. & Yan, S.-J. (1982). Org. React.28, 37–201.
  • Collet, A., Brienne, M.-J. & Jacques, J. (1980). Chem. Rev.80, 215–230.
  • CrystalMaker (2005). CrystalMaker CrystalMaker Software Ltd, Yarnton, Oxfordshire, England. www.CrystalMaker.co.uk.
  • Jacques, J., Collet, A. & Wilen, S. H. (1981). Enantiomers, Racemates, and Resolutions New York: Wiley.
  • Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Marjo, C. E., Scudder, M. L., Craig, D. C. & Bishop, R. (1997). J. Chem. Soc., Perkin Trans. 2, pp. 2099–2104.
  • Peet, N. P. & Cargill, R. G. (1973). J. Org. Chem.38, 4281–4285.
  • Rae, A. D. (2000). RAELS Australian National University.
  • Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual Enraf–Nonius, Delft, The Netherlands.
  • Smith, L. I. & Opie, J. W. (1955). Org. Synth. Coll.3, 56–58.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography