2,3,10,11-Tetra­meth­oxy-6,7,14,15-tetra­hydro-6,14-methano­cyclo­octa­[1,2-b;5,6-b′]diquinoline

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

doi:10.1107/S1600536807061235

organic compounds

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2,3,10,11-Tetramethoxy-6,7,14,15-tetrahydro-6,14-methanocycloocta[1,2-b;5,6-b′]diquinoline

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

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

(Received 18 November 2007; accepted 20 November 2007; online 6 December 2007)

The racemic title compound, C₂₇H₂₆N₂O₄, crystallizes with its central carbon bridge on a twofold axis. It forms parallel chains of molecules utilizing aryl offset face–face interactions with an interplanar distance of about 3.5 Å. These chains associate further by means of pairs of O—CH₂—H⋯π (with H–ring distances ranging from 2.69 to 2.95 Å) and O—CH₂—H⋯N motifs. The methoxy groups in this structure are coplanar with the aromatic rings to which they are attached. This is recognized as being common behaviour amongst aromatic methoxy compounds.

Related literature

Condensation of two equivalents of a 2-aminobenzaldehyde derivative with one of bicyclo[3.3.1]nonane-2,6-dione provides a V-shaped diquinoline adduct by means of the Friedländer condensation (Cheng & Yan, 1982 ). Substituted molecules of this general structural type frequently act as lattice inclusion hosts (Bishop, 2006 ). For related literature, see: Allen (2002 ); Desiraju & Gavezzotti (1989 ); Marjo et al. (1997 ); Pendrak et al. (1995 ); Schaefer & Honig (1968 ).

Experimental

Crystal data

C₂₇H₂₆N₂O₄
M_r = 442.5
Monoclinic, C 2/c
a = 14.137 (7) Å
b = 9.533 (6) Å
c = 16.551 (7) Å
β = 100.79 (3)°
V = 2191 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.12 mm (radius)

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1999 measured reflections
1926 independent reflections
803 reflections with I > 2σ(I)
R_int = 0.062
1 standard reflection frequency: 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.053
S = 1.41
803 reflections
150 parameters
H-atom parameters not refined
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H3C14⋯N1ⁱ	1.00	2.88	3.723 (5)	142
C14—H3C14⋯N1ⁱⁱ	1.00	2.96	3.348 (5)	104
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Schagen et al., 1989 ); cell refinement: CAD-4 Software; 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: https://doi.org/10.1107/S1600536807061235/ln2008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061235/ln2008Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, (1), contains half a molecule, with the central bridging carbon atom located on a twofold axis (Fig. 1).

Molecules of (1) form parallel chains along the ac diagonal (Fig. 2), associating by means of exo,exo-facial aryl offset face-face (OFF) interactions (Desiraju & Gavezzotti, 1989). The distance between the aromatic planes is about 3.5 Å. Complementary to the π···π interaction are a pair of associations between a methoxy group and a quinoline N atom (O—CH₂—H···N; d = 2.88 Å), and a pair between an aliphatic methylene and a methoxy group (C—H···O—CH₃, d = 2.84 Å). Adjacent chains interact in two ways: by means of a double centrosymmetric O—CH₂—H···π interaction (utilizing the 3-methoxy group, with shortest C···C contacts of 3.57 and 3.82 Å) and an O—CH₂—H···N interaction (utilizing the 10-methoxy group with C···N of 3.35 Å).

It is noteworthy that the methoxy groups in this structure are co-planar with the aromatic rings to which they are attached. The Cambridge Structural Database (Allen et al., 2002) reveals that this situation is commonplace amongst related compounds. The steric effects resulting from this co-planarity would be sufficient cause for the absence of centrosymmetric dimers utilizing the edge-edge aryl C—H···N supramolecular synthon which are found in the parent the non-methoxy diquinoline adduct (Marjo et al., 1997).

Related literature top

Condensation of two equivalents of a 2-aminobenzaldehyde derivative with one of bicyclo[3.3.1]nonane-2,6-dione provides a V-shaped diquinoline adduct by means of the Friedländer condensation (Cheng & Yan, 1982). Substituted molecules of this general structural type frequently act as lattice inclusion hosts (Bishop, 2006). For related literature, see: Allen (2002); Desiraju & Gavezzotti (1989); Marjo et al. (1997); Pendrak et al. (1995); Schaefer & Honig (1968).

Experimental top

2-Amino-4,5-dimethoxybenzaldehyde (Pendrak et al., 1995) (1.20 g, 6.62 mmol) and bicyclo[3.3.1]nonane-2,6-dione (Schaefer & Honig, 1968) (0.38 g, 2.50 mol) were dissolved in hot ethanol (20 ml) and a solution of sodium hydroxide (0.49 g, 12.25 mmol) in ethanol (10 ml) was added. The mixture was refluxed for 5 h, allowed to cool, then kept at 273 K for 5 h. Filtration gave the product 1 (0.51 g, 46%) of m.p. 548–549 K. ¹³C NMR (75.5 MHz, CDCl₃) δ: 29.5 (CH₂), 36.6 (CH), 38.2 (CH₂), 56.2 (CH₃), 56.4 (CH₃), 104.6 (CH), 107.4 (CH), 123.3 (C), 126.8 (C), 134.7 (CH), 144.3 (C), 149.7 (C), 152.3 (C), 159.2 (C); ¹H NMR (300 MHz, CDCl₃) δ: 2.49 (br s, 2H), 3.25 & 3.32 (d, 2H, J_AB 16.6 Hz), 3.42 & 3.49 (dd, 2H, J_AB 16.6, J_BX 5.3 Hz), 3.70 (d, 2H, J 2.6 Hz), 3.91 (s, 6H), 3.99 (s, 6H), 6.79 (s, 2H), 7.32 (s, 2H), 7.50 (s, 2H). X-ray quality crystals were obtained from ethyl acetate solution.

Structure description top

The asymmetric unit of the title compound, (1), contains half a molecule, with the central bridging carbon atom located on a twofold axis (Fig. 1).

Condensation of two equivalents of a 2-aminobenzaldehyde derivative with one of bicyclo[3.3.1]nonane-2,6-dione provides a V-shaped diquinoline adduct by means of the Friedländer condensation (Cheng & Yan, 1982). Substituted molecules of this general structural type frequently act as lattice inclusion hosts (Bishop, 2006). For related literature, see: Allen (2002); Desiraju & Gavezzotti (1989); Marjo et al. (1997); Pendrak et al. (1995); Schaefer & Honig (1968).

Computing details top

Data collection: CAD-4 Software (Schagen et al., 1989); cell refinement: CAD-4 Software (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 (1), with ellipsoids drawn at 30% probability level. Symmetry code: (i) 1 - x, y, 3/2 - z.
	Fig. 2. The chain of molecules of (1) with centrosymmetric OFF interactions between exo-surfaces of the aromatic wings. Adjacent molecules are of the opposite chirality.
	Fig. 3. The chain (top) interacts with adjacent chains in two ways: a double CH₃···π interaction (pair of arrows at the bottom of the figure) and a CH₃···N interaction (at the left of the figure).

2,3,10,11-Tetramethoxy-6,7,14,15-tetrahydro-6,14- methanocycloocta[1,2 - b;5,6-b']diquinoline top

Crystal data top

C₂₇H₂₆N₂O₄	F(000) = 936.0
M_r = 442.5	D_x = 1.34 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.137 (7) Å	Cell parameters from 11 reflections
b = 9.533 (6) Å	θ = 10–11°
c = 16.551 (7) Å	µ = 0.09 mm⁻¹
β = 100.79 (3)°	T = 294 K
V = 2191 (2) Å³	Irregular, colourless
Z = 4	0.12 mm (radius)

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 25°
ω–2θ scans	h = −16→16
1999 measured reflections	k = 0→11
1926 independent reflections	l = 0→19
803 reflections with I > 2σ(I)	1 standard reflections every 30 min
R_int = 0.062	intensity decay: none

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.050	H-atom parameters not refined
wR(F²) = 0.053	w = 1/[σ²(F) + 0.0004F²]
S = 1.41	(Δ/σ)_max = 0.001
803 reflections	Δρ_max = 0.56 e Å⁻³
150 parameters	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₂₇H₂₆N₂O₄	V = 2191 (2) Å³
M_r = 442.5	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.137 (7) Å	µ = 0.09 mm⁻¹
b = 9.533 (6) Å	T = 294 K
c = 16.551 (7) Å	0.12 mm (radius)
β = 100.79 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.062
1999 measured reflections	1 standard reflections every 30 min
1926 independent reflections	intensity decay: none
803 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.053	H-atom parameters not refined
S = 1.41	Δρ_max = 0.56 e Å⁻³
803 reflections	Δρ_min = −0.48 e Å⁻³
150 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.3447 (2)	−0.0160 (3)	0.3564 (2)	0.059 (1)
O2	0.2109 (2)	−0.1040 (3)	0.4273 (2)	0.0559 (9)
N1	0.4643 (2)	0.2977 (4)	0.5789 (2)	0.047 (1)
C1	0.5320 (4)	0.4581 (5)	0.6853 (3)	0.055 (1)
C2	0.4554 (3)	0.3525 (4)	0.6509 (3)	0.043 (1)
C3	0.3824 (3)	0.3145 (5)	0.6937 (3)	0.045 (1)
C4	0.3736 (3)	0.3841 (5)	0.7746 (3)	0.054 (1)
C5	0.5000	0.5529 (7)	0.7500	0.062 (2)
C6	0.3986 (3)	0.1982 (4)	0.5451 (3)	0.041 (1)
C7	0.4076 (3)	0.1425 (5)	0.4682 (2)	0.042 (1)
C8	0.3440 (3)	0.0430 (5)	0.4314 (3)	0.043 (1)
C9	0.2697 (3)	−0.0039 (5)	0.4705 (3)	0.042 (1)
C10	0.2596 (3)	0.0469 (4)	0.5446 (3)	0.044 (1)
C11	0.3242 (3)	0.1518 (5)	0.5843 (2)	0.042 (1)
C12	0.3174 (3)	0.2147 (5)	0.6597 (3)	0.045 (1)
C13	0.4183 (4)	0.0306 (6)	0.3148 (3)	0.076 (2)
C14	0.1350 (3)	−0.1571 (5)	0.4654 (3)	0.061 (1)
HC1	0.5453	0.5182	0.6392	0.055
H1C4	0.3577	0.3110	0.8132	0.054
H2C4	0.3207	0.4552	0.7640	0.054
H1C5	0.4451	0.6135	0.7235	0.062	0.5
H2C5	0.5549	0.6135	0.7765	0.062	0.5
HC7	0.4605	0.1755	0.4404	0.042
HC10	0.2068	0.0110	0.5717	0.044
HC12	0.2646	0.1863	0.6889	0.045
H1C13	0.4120	−0.0191	0.2609	0.076
H2C13	0.4118	0.1340	0.3051	0.076
H3C13	0.4827	0.0098	0.3492	0.076
H1C14	0.0972	−0.2287	0.4287	0.061
H2C14	0.1634	−0.2014	0.5193	0.061
H3C14	0.0917	−0.0783	0.4748	0.061

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.058 (2)	0.066 (2)	0.055 (2)	−0.016 (2)	0.018 (2)	−0.021 (2)
O2	0.050 (2)	0.057 (2)	0.060 (2)	−0.014 (2)	0.007 (2)	0.003 (2)
N1	0.049 (2)	0.050 (3)	0.040 (2)	−0.007 (2)	0.000 (2)	0.002 (2)
C1	0.067 (3)	0.050 (3)	0.044 (3)	−0.007 (3)	0.000 (3)	0.004 (3)
C2	0.049 (3)	0.039 (3)	0.040 (3)	0.005 (2)	0.001 (2)	0.004 (3)
C3	0.046 (3)	0.047 (3)	0.039 (3)	0.009 (2)	0.001 (2)	0.007 (2)
C4	0.060 (3)	0.060 (3)	0.039 (3)	0.020 (3)	−0.001 (2)	−0.006 (3)
C5	0.089 (6)	0.045 (5)	0.048 (4)	0.0000	−0.002 (4)	0.0000
C6	0.039 (3)	0.044 (3)	0.038 (3)	0.006 (2)	0.002 (2)	0.007 (2)
C7	0.036 (3)	0.054 (3)	0.039 (3)	−0.006 (2)	0.010 (2)	−0.003 (3)
C8	0.042 (3)	0.045 (3)	0.040 (3)	0.006 (2)	0.007 (2)	0.002 (3)
C9	0.036 (3)	0.041 (3)	0.047 (3)	−0.006 (2)	0.001 (2)	0.001 (3)
C10	0.038 (3)	0.043 (3)	0.051 (3)	−0.003 (2)	0.006 (2)	0.006 (2)
C11	0.042 (3)	0.044 (3)	0.040 (3)	0.006 (3)	0.007 (2)	0.013 (3)
C12	0.043 (3)	0.054 (3)	0.038 (3)	0.006 (3)	0.007 (2)	0.012 (2)
C13	0.074 (4)	0.106 (5)	0.056 (3)	−0.032 (3)	0.029 (3)	−0.029 (3)
C14	0.050 (3)	0.060 (3)	0.072 (3)	−0.017 (3)	0.004 (3)	0.008 (3)

Geometric parameters (Å, º) top

O1—C8	1.365 (4)	C6—C7	1.406 (5)
O1—C13	1.421 (5)	C6—C11	1.407 (5)
O2—C9	1.375 (5)	C7—C8	1.369 (5)
O2—C14	1.434 (4)	C7—HC7	1.000
N1—C2	1.328 (5)	C8—C9	1.406 (5)
N1—C6	1.371 (5)	C9—C10	1.352 (5)
C1—C2	1.510 (6)	C10—C11	1.428 (5)
C1—C4ⁱ	1.545 (6)	C10—HC10	1.000
C1—C5	1.532 (5)	C11—C12	1.405 (5)
C1—HC1	1.000	C12—HC12	1.000
C2—C3	1.405 (5)	C13—H1C13	1.000
C3—C4	1.520 (5)	C13—H2C13	1.000
C3—C12	1.368 (5)	C13—H3C13	1.000
C4—H1C4	1.000	C14—H1C14	1.000
C4—H2C4	1.000	C14—H2C14	1.000
C5—H1C5	1.000	C14—H3C14	1.000
C5—H2C5	1.000

C8—O1—C13	116.3 (4)	C6—C7—C8	120.1 (4)
C9—O2—C14	116.5 (3)	C6—C7—HC7	119.9
C2—N1—C6	117.9 (4)	C8—C7—HC7	119.9
C2—C1—C4ⁱ	111.0 (4)	O1—C8—C7	125.1 (4)
C2—C1—C5	111.9 (4)	O1—C8—C9	114.9 (4)
C2—C1—HC1	108.6	C7—C8—C9	120.0 (4)
C4ⁱ—C1—C5	108.3 (3)	O2—C9—C8	114.4 (4)
C4ⁱ—C1—HC1	108.6	O2—C9—C10	124.3 (4)
C5—C1—HC1	108.6	C8—C9—C10	121.3 (4)
N1—C2—C1	114.8 (4)	C9—C10—C11	120.0 (4)
N1—C2—C3	123.6 (4)	C9—C10—HC10	120.0
C1—C2—C3	121.6 (4)	C11—C10—HC10	120.0
C2—C3—C4	121.3 (4)	C6—C11—C10	118.5 (4)
C2—C3—C12	118.2 (4)	C6—C11—C12	117.2 (4)
C4—C3—C12	120.5 (4)	C10—C11—C12	124.3 (4)
C1ⁱ—C4—C3	111.8 (4)	C3—C12—C11	120.7 (4)
C1ⁱ—C4—H1C4	108.9	C3—C12—HC12	119.7
C1ⁱ—C4—H2C4	108.9	C11—C12—HC12	119.7
C3—C4—H1C4	108.9	O1—C13—H1C13	109.5
C3—C4—H2C4	108.9	O1—C13—H2C13	109.5
H1C4—C4—H2C4	109.5	O1—C13—H3C13	109.5
C1—C5—C1ⁱ	107.7 (5)	H1C13—C13—H2C13	109.5
C1—C5—H1C5	109.9	H1C13—C13—H3C13	109.5
C1—C5—H2C5	109.9	H2C13—C13—H3C13	109.5
C1ⁱ—C5—H1C5	109.9	O2—C14—H1C14	109.5
C1ⁱ—C5—H2C5	109.9	O2—C14—H2C14	109.5
H1C5—C5—H2C5	109.5	O2—C14—H3C14	109.5
N1—C6—C7	117.5 (4)	H1C14—C14—H2C14	109.5
N1—C6—C11	122.5 (4)	H1C14—C14—H3C14	109.5
C7—C6—C11	120.0 (4)	H2C14—C14—H3C14	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H3C14···N1ⁱⁱ	1.00	2.882	3.723 (5)	142
C14—H3C14···N1ⁱⁱⁱ	1.00	2.958	3.348 (5)	104

Symmetry codes: (ii) −x+1/2, −y+1/2, −z+1; (iii) x−1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆N₂O₄
M_r	442.5
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	14.137 (7), 9.533 (6), 16.551 (7)
β (°)	100.79 (3)
V (Å³)	2191 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 (radius)

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1999, 1926, 803
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.053, 1.41
No. of reflections	803
No. of parameters	150
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.48

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H3C14···N1ⁱ	1.00	2.882	3.723 (5)	142
C14—H3C14···N1ⁱⁱ	1.00	2.958	3.348 (5)	104

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) x−1/2, y−1/2, z.

Acknowledgements

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

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bishop, R. (2006). Crystal Engineering of Halogenated Heteroaromatic Clathrate Systems. In Frontiers in Crystal Engineering, ch. 5, pp. 91–116, edited by E. R. T. Tiekink & J. J. Vittal. Chichester: Wiley. Google Scholar
Cheng, C.-C. & Yan, S.-J. (1982). Org. React. 28, 37–201. CAS Google Scholar
CrystalMaker (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. http://www.crystalmaker.co.uk. Google Scholar
Desiraju, G. R. & Gavezzotti, A. (1989). Acta Cryst. B45, 473–482. CrossRef CAS Web of Science IUCr Journals Google Scholar
Johnson, C. K. (1976). ORTEPII, Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Marjo, C. E., Scudder, M. L., Craig, D. C. & Bishop, R. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 2099–2104. CrossRef Google Scholar
Pendrak, I., Wittrock, R. & Kingsbury, W. D. (1995). J. Org. Chem. 60, 2912–2915. CrossRef CAS Web of Science Google Scholar
Rae, A. D. (2000). RAELS. Australian National University, Canberra. Google Scholar
Schaefer, J. P. & Honig, L. M. (1968). J. Org. Chem. 33, 2655–2659. CrossRef CAS Web of Science Google Scholar
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands. Google Scholar

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2,3,10,11-Tetra­meth­­oxy-6,7,14,15-tetra­hydro-6,14-methano­cyclo­octa­[1,2-b;5,6-b′]di­quinoline

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,3,10,11-Tetramethoxy-6,7,14,15-tetrahydro-6,14-methanocycloocta[1,2-b;5,6-b′]diquinoline