(6aS*,6bS*,11R*,11aR*)-6-(2-Furyl­methyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octa­hydro­furo[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carb­oxy­lic acid

Obushak, M.D.; Horak, Y.I.; Zaytsev, V.P.; Motorygina, E.L.; Zubkov, F.I.; Khrustalev, V.N.

doi:10.1107/S160053681104311X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o3031-o3032

doi:10.1107/S160053681104311X

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(6aS,6bS,11R,11aR)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid

Mykola D. Obushak,^a ^* Yuri I. Horak,^a Vladimir P. Zaytsev,^b Ekaterina L. Motorygina,^b Fedor I. Zubkov ^b and Victor N. Khrustalev ^c

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya Street, Lviv 79005, Ukraine, ^bOrganic Chemistry Department, Russian People's Friendship University, Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation, and ^cX-ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: obushak@in.lviv.ua

(Received 13 October 2011; accepted 18 October 2011; online 29 October 2011)

The title compound, C₂₃H₁₈N₂O₆, is the product of an intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline. The molecule comprises a previously unknown fused pentacyclic system containing two five-membered rings (2-pyrrolidinone and furan) and three six-membered rings (benzene, 2,3-dihydro-4-pyrimidinone and dihydrocyclohexane). The central five-membered pyrrolidinone ring has the usual envelope conformation. The six-membered dihydropyrimidinone and dihydrocyclohexane rings adopt a half-boat and a half-chair conformation, respectively. The dihedral angle between the planes of the terminal benzene and furan rings is 45.99 (7)°. In the crystal, O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. Weak C—H⋯O hydrogen bonds consolidate further the crystal packing, which exhibits π–π interactions, with a short distance of 3.556 (3) Å between the centroids of benzene rings of neighbouring molecules.

Related literature

For 2-vinylfurans as dienes, see: Kotsuki et al. (1981 ); Keil et al. (1990 ); Kusurkar & Bhosale (1990 ); Anisimova et al. (2006 ). For the intramolecular Diels–Alder reaction for furan (IMDAF), see: Vogel et al. (1999 ); Zubkov et al. (2005 , 2009 , 2010 ). For related compounds, see: Chou & Tsai (1992 ); Chou et al. (1997 ); Sun & Murray (1999 ); Ohno et al. (2005 ); Patre et al. (2007 ).

Experimental

Crystal data

C₂₃H₁₈N₂O₆
M_r = 418.39
Monoclinic, P 2₁ /n
a = 8.2364 (5) Å
b = 16.9882 (10) Å
c = 13.1568 (8) Å
β = 99.102 (1)°
V = 1817.74 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.967, T_max = 0.980
21001 measured reflections
5293 independent reflections
4139 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.160
S = 1.00
5293 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1ⁱ	0.93	1.75	2.671 (2)	174
C2—H2⋯O3ⁱⁱ	0.95	2.42	3.326 (2)	160
C3—H3⋯O3ⁱⁱⁱ	0.95	2.56	3.384 (2)	146
C7—H7B⋯O4^iv	0.99	2.54	3.455 (2)	155
C11A—H11A⋯O1^v	1.00	2.38	3.325 (2)	157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+2, -y+1, -z; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681104311X/cv5175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104311X/cv5175Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681104311X/cv5175Isup3.cml

checkCIF report

Comment top

Currently, there are only a few reports concerning the [4 + 2] cycloaddition of 2-vinylfurans with dienophiles (Kotsuki et al., 1981; Keil et al., 1990; Kusurkar & Bhosale, 1990; Anisimova et al., 2006). In the present work, within the scope of our investigations on the intramolecular Diels-Alder reaction of furan (IMDAF) (Vogel et al., 1999; Zubkov et al., 2005, 2009, 2010), we demonstrate the possibility of intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline. The latter is an intermediate of a reaction of 2-[(E)-2-(2-furyl)vinyl]-2,3-dihydroquinazolin-4-one with maleic anhydride (Figure 1). The reaction product contains a previously unknown pentacycle bearing four asymmetrical centers. The main structural fragments of the new pentacycle are quinazoline and furo[2,3-f]isoindole (Chou & Tsai, 1992; Chou et al., 1997; Sun & Murray, 1999; Ohno et al., 2005; Patre et al., 2007). The structure of the final product - 6-(2-furylmethyl)-5,12-dioxo-5,6,6a,6 b,7,11,11a,12-octahydrofuro[3',2':5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid, C₂₃H₁₈N₂O₆, (I) was unambiguously established by X-ray diffraction study.

Molecule of (I) comprises a fused pentacyclic system containing two five-membered rings (2-pyrrolidinone and furan) and three six-membered rings (benzene, 2,3-dihydro-4-pyrimidinone and dihydrocyclohexane) (Figure 2). The central five-membered pyrrolidinone ring has usual envelope conformation (the C6B carbon atom is out of the plane through the other atoms of the ring by 0.477 (2) Å)), and the central six-membered dihydropyrimidinone and dihydrocyclohexane rings adopt the nonsymmetrical half-boat (the N6 nitrogen and C6A carbon atoms are out of the plane through the other atoms of the ring by 0.265 (3) and 0.626 (3) Å, respectively) and nonsymmetrical half-chair (the C6B and C11A carbon atoms are out of the plane through the other atoms of the ring by -0.555 (3) and 0.281 (3) Å, respectively) conformations, respectively. The dihedral angle between the planes of the end-cutting benzene and furan rings is 45.99 (7)°.

The furylmethyl ligand and carboxylic acid substituent at the C11 atom arrange from different sides of the main pentacyclic framework. Apparently, such disposition is explained by the fact that, in the crystal, the molecules of (I) form the centrosymmerical dimers through the intermolecular O4—H4O···O1ⁱ hydrogen bonding interactions (Table 1). Furthermore, due to the steric reasons within the dimers, the nitrogen N6 atom adopts a trigonal-pyramidal geometry (sum of the bond angles is 357.5°), while the nitrogen N13 atom has a trigonal-planar geometry (sum of the bond angles is 360.0°). Weak intermolecular C—H···O hydrogen bonds consolidate further the crystal packing, which exhibits π—π interactions with the short distance of 3.556 (3) Å between the centroids of benzene rings from the neighbouring molecules [Cg···Cgⁱ; symmetry code (i) 1 - x, 1 - y, -z].

The molecule of (I) possesses four asymmetric centers at the C6A, C6B, C11 and C11A carbon atoms and can have potentially numerous diastereomers. The crystal of (I) is racemic and consists of enantiomeric pairs with the following relative configuration of the centers: rac-6aS*,6 bS*,11R*,11aR*.

Related literature top

For 2-vinylfurans as dienes, see: Kotsuki et al. (1981); Keil et al. (1990); Kusurkar & Bhosale (1990); Anisimova et al. (2006). For the intramolecular Diels–Alder reaction for furan (IMDAF), see: Vogel et al. (1999); Zubkov et al. (2005, 2009, 2010). For related compounds, see: Chou & Tsai (1992); Chou et al. (1997); Sun & Murray (1999); Ohno et al. (2005); Patre et al. (2007).

Experimental top

A mixture of the initial 3-(2-furylmethyl)-2-[(E)-2-(2-furyl)vinyl]-2,3-dihydroquinazolin-4(1H)-one (0.5 g, 1.6 mmol) and maleic anhydride (0.17 g, 1.7 mmol) was refluxed for 8 h in toluene (10 ml). At the end of the reaction the resulting mixture was cooled, and formed brown precipitate was filtered off, washed with benzene(2x10 ml) and ether (2x10 ml). Further crystallization from an ethanol-DMF mixture gives the corresponding acid (0.5 g, 1.2 mmol) as orange prism. Yield is 77%. The single-crystal of the product was obtained by slow crystallization from an ethanol-ethyl acetate mixture. M.p. = 499–500 K. IR (KBr), ν/cm^-1: 1630, 1727 (NCO, CO₂H). ¹H NMR (600 MHz, DMSO-d₆, 293 K): δ = 12.7 (br.s,1H, CO₂H), 8.24 (d, 1H,H4, J_4,3 = 7.8), 7.93 (d, 1H, H1, J_1,2 = 7.8), 7.60 (t, 1H, H2, J_1,2 = J_2,3 = 7.8), 7.57 (dd, 1H, H5', J_4',5'= 1.8, J_3',5' = 0.8), 7.54 (d, 1H, H9, J_9,10 = 0.9), 7.25 (t, 1H, H3, J_2,3 = J_3,4 = 7.8), 6.44 (d, 1H, H10, J_9,10= 0.9), 6.38 (dd, 1H, H4', J_3',4' = 3.2, J_4',5' = 1.8), 6.32 (d, 1H, H3', J_3',4' = 3.2), 5.53 (d, 1H, H6A, J_{6 A,6B} = 8.2), 5.01 (d, 1H, NCH₂, J_H14A,H14B = 16.9), 4.73 (d,1H, NCH₂, J_H14A,H14B = 16.9), 3.83 (d, 1H, H₁₁, J_{11,11 A} = 5.0), 3.29 (m, 1H, H6B), 3.16 (dd, 1H, H7A, J_{7 A,7B} = 15.6, J_{7 A,6B} = 4.6), 3.04 (dd, 1H, H11A, J_{11 A,6B} = 12.4, J_{11,11 A} = 5.0), 2.70 (dd, 1H, H7B, J_{7 A,7B} = 15.6, J_7B,6B = 11.5). Mass spectrum (EI—MS, 70 eV) m/z(I_r, (%)): 418 [M⁺] (100), 374 (22), 322 (18), 276 (41), 236 (13), 227 (16), 185 (12), 147 (13), 119 (14), 91 (37), 81 (75), 53 (12). Anal. Calcd. for C₂₃H₁₈N₂O₆: C, 66.02; H, 4.34; N, 6.70. Found: C, 66.12; H, 4.04; N, 6.83.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction of 2-[(E)-2-(2-furyl)vinyl]-2,3-dihydroquinazolin-4-one with maleic anhydride.
	Fig. 2. Molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level.

(6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12- dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3',2':5,6]isoindolo[2,1- a]quinazoline-11-carboxylic acid top

Crystal data top

C₂₃H₁₈N₂O₆	F(000) = 872
M_r = 418.39	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6904 reflections
a = 8.2364 (5) Å	θ = 2.4–30.0°
b = 16.9882 (10) Å	µ = 0.11 mm⁻¹
c = 13.1568 (8) Å	T = 100 K
β = 99.102 (1)°	Prism, orange
V = 1817.74 (19) Å³	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	5293 independent reflections
Radiation source: fine-focus sealed tube	4139 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
T_min = 0.967, T_max = 0.980	k = −23→23
21001 measured reflections	l = −18→18

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)] = 0.060	Hydrogen site location: difference Fourier map
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.08P)² + 1.9P] where P = (F_o² + 2F_c²)/3
5293 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₃H₁₈N₂O₆	V = 1817.74 (19) Å³
M_r = 418.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2364 (5) Å	µ = 0.11 mm⁻¹
b = 16.9882 (10) Å	T = 100 K
c = 13.1568 (8) Å	0.30 × 0.20 × 0.18 mm
β = 99.102 (1)°

Data collection top

Bruker SMART 1K CCD diffractometer	5293 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	4139 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.980	R_int = 0.027
21001 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	Δρ_max = 0.45 e Å⁻³
5293 reflections	Δρ_min = −0.34 e Å⁻³
280 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 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
O1	0.77116 (15)	0.37826 (7)	0.24161 (9)	0.0235 (3)
O2	0.73217 (17)	0.53678 (7)	0.48118 (10)	0.0286 (3)
O3	0.47571 (15)	0.62107 (7)	−0.02374 (9)	0.0245 (3)
O4	0.31904 (17)	0.72270 (7)	−0.08729 (10)	0.0284 (3)
H4O	0.2827	0.6861	−0.1383	0.043*
O5	0.82503 (15)	0.69632 (7)	0.03174 (9)	0.0237 (3)
C1	1.0826 (2)	0.57749 (10)	0.10046 (13)	0.0221 (3)
H1	1.0901	0.6300	0.0769	0.027*
C2	1.2040 (2)	0.52240 (10)	0.08887 (13)	0.0237 (3)
H2	1.2942	0.5378	0.0565	0.028*
C3	1.1958 (2)	0.44550 (10)	0.12353 (13)	0.0248 (3)
H3	1.2811	0.4092	0.1165	0.030*
C4	1.0627 (2)	0.42198 (10)	0.16832 (13)	0.0231 (3)
H4	1.0557	0.3693	0.1914	0.028*
C4A	0.93842 (19)	0.47584 (9)	0.17967 (12)	0.0197 (3)
C5	0.7966 (2)	0.44955 (9)	0.22637 (12)	0.0203 (3)
N6	0.69629 (17)	0.50537 (8)	0.25528 (10)	0.0198 (3)
C6A	0.72967 (19)	0.59004 (9)	0.24741 (12)	0.0188 (3)
H6A	0.7925	0.6104	0.3135	0.023*
C6B	0.57091 (19)	0.63798 (9)	0.21574 (12)	0.0192 (3)
H6B	0.4918	0.6042	0.1694	0.023*
C7	0.4786 (2)	0.67373 (10)	0.29657 (13)	0.0224 (3)
H7A	0.4284	0.6322	0.3343	0.027*
H7B	0.5529	0.7060	0.3465	0.027*
C7A	0.3497 (2)	0.72356 (9)	0.23479 (13)	0.0220 (3)
O8	0.20912 (15)	0.74143 (7)	0.27305 (10)	0.0246 (3)
C9	0.1130 (2)	0.78350 (10)	0.19758 (14)	0.0257 (3)
H9	0.0071	0.8036	0.2030	0.031*
C10	0.1885 (2)	0.79273 (10)	0.11445 (14)	0.0240 (3)
H10	0.1471	0.8199	0.0526	0.029*
C10A	0.3445 (2)	0.75302 (9)	0.13854 (13)	0.0208 (3)
C11	0.4827 (2)	0.74087 (9)	0.07672 (12)	0.0202 (3)
H11	0.5173	0.7930	0.0522	0.024*
C11A	0.62601 (19)	0.70466 (9)	0.15030 (12)	0.0189 (3)
H11A	0.6735	0.7472	0.1986	0.023*
C12	0.76530 (19)	0.67005 (9)	0.10328 (12)	0.0196 (3)
N13	0.82043 (16)	0.60449 (8)	0.16182 (10)	0.0196 (3)
C13A	0.95024 (19)	0.55390 (9)	0.14728 (12)	0.0193 (3)
C14	0.5826 (2)	0.48033 (9)	0.32540 (13)	0.0220 (3)
H14A	0.5286	0.4304	0.3003	0.026*
H14B	0.4961	0.5207	0.3261	0.026*
C15	0.6729 (2)	0.46908 (10)	0.43133 (13)	0.0220 (3)
C16	0.7223 (2)	0.40551 (10)	0.48999 (13)	0.0244 (3)
H16	0.6980	0.3520	0.4731	0.029*
C17	0.8185 (2)	0.43469 (12)	0.58253 (14)	0.0290 (4)
H17	0.8700	0.4044	0.6393	0.035*
C18	0.8216 (3)	0.51364 (12)	0.57333 (14)	0.0325 (4)
H18	0.8777	0.5484	0.6236	0.039*
C19	0.4283 (2)	0.68777 (10)	−0.01577 (12)	0.0212 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0327 (6)	0.0167 (5)	0.0209 (6)	−0.0006 (4)	0.0031 (5)	0.0008 (4)
O2	0.0387 (7)	0.0233 (6)	0.0229 (6)	−0.0022 (5)	0.0021 (5)	−0.0022 (5)
O3	0.0280 (6)	0.0195 (6)	0.0251 (6)	0.0020 (4)	0.0017 (5)	−0.0018 (4)
O4	0.0352 (7)	0.0225 (6)	0.0241 (6)	0.0061 (5)	−0.0060 (5)	−0.0028 (5)
O5	0.0253 (6)	0.0211 (6)	0.0250 (6)	−0.0016 (4)	0.0055 (5)	0.0028 (4)
C1	0.0214 (7)	0.0221 (7)	0.0222 (7)	−0.0022 (6)	0.0015 (6)	−0.0004 (6)
C2	0.0204 (7)	0.0285 (8)	0.0217 (8)	−0.0005 (6)	0.0017 (6)	−0.0034 (6)
C3	0.0248 (8)	0.0270 (8)	0.0217 (7)	0.0044 (6)	0.0011 (6)	−0.0023 (6)
C4	0.0289 (8)	0.0198 (7)	0.0199 (7)	0.0044 (6)	0.0014 (6)	0.0005 (6)
C4A	0.0232 (7)	0.0184 (7)	0.0169 (7)	0.0007 (5)	0.0017 (5)	−0.0006 (5)
C5	0.0242 (7)	0.0182 (7)	0.0174 (7)	0.0001 (5)	−0.0006 (6)	0.0011 (5)
N6	0.0230 (6)	0.0166 (6)	0.0198 (6)	−0.0007 (5)	0.0032 (5)	0.0011 (5)
C6A	0.0212 (7)	0.0160 (7)	0.0188 (7)	−0.0010 (5)	0.0016 (5)	0.0008 (5)
C6B	0.0203 (7)	0.0182 (7)	0.0188 (7)	0.0005 (5)	0.0017 (5)	0.0022 (5)
C7	0.0239 (7)	0.0225 (7)	0.0212 (7)	0.0011 (6)	0.0044 (6)	0.0011 (6)
C7A	0.0221 (7)	0.0187 (7)	0.0251 (8)	0.0000 (5)	0.0037 (6)	−0.0031 (6)
O8	0.0239 (6)	0.0223 (6)	0.0284 (6)	0.0025 (4)	0.0066 (5)	−0.0004 (5)
C9	0.0243 (8)	0.0202 (7)	0.0321 (9)	0.0026 (6)	0.0030 (6)	−0.0017 (6)
C10	0.0237 (7)	0.0196 (7)	0.0279 (8)	0.0020 (6)	0.0009 (6)	−0.0016 (6)
C10A	0.0225 (7)	0.0159 (7)	0.0235 (8)	−0.0001 (5)	0.0019 (6)	−0.0020 (5)
C11	0.0224 (7)	0.0166 (7)	0.0210 (7)	0.0006 (5)	0.0017 (6)	0.0007 (5)
C11A	0.0201 (7)	0.0165 (6)	0.0195 (7)	−0.0015 (5)	0.0010 (5)	0.0002 (5)
C12	0.0213 (7)	0.0163 (6)	0.0203 (7)	−0.0021 (5)	0.0011 (5)	−0.0009 (5)
N13	0.0200 (6)	0.0172 (6)	0.0216 (6)	0.0008 (5)	0.0034 (5)	0.0019 (5)
C13A	0.0192 (7)	0.0198 (7)	0.0181 (7)	0.0007 (5)	0.0002 (5)	0.0001 (5)
C14	0.0211 (7)	0.0189 (7)	0.0264 (8)	−0.0011 (5)	0.0044 (6)	0.0032 (6)
C15	0.0240 (7)	0.0207 (7)	0.0221 (7)	−0.0005 (6)	0.0056 (6)	−0.0005 (6)
C16	0.0243 (8)	0.0243 (8)	0.0252 (8)	0.0001 (6)	0.0058 (6)	0.0032 (6)
C17	0.0288 (8)	0.0358 (9)	0.0229 (8)	0.0001 (7)	0.0051 (7)	0.0046 (7)
C18	0.0394 (10)	0.0372 (10)	0.0201 (8)	−0.0038 (8)	0.0019 (7)	−0.0021 (7)
C19	0.0218 (7)	0.0207 (7)	0.0209 (7)	0.0002 (6)	0.0026 (6)	0.0008 (6)

Geometric parameters (Å, º) top

O1—C5	1.2507 (19)	C7—C7A	1.494 (2)
O2—C18	1.373 (2)	C7—H7A	0.9900
O2—C15	1.375 (2)	C7—H7B	0.9900
O3—C19	1.209 (2)	C7A—C10A	1.356 (2)
O4—C19	1.334 (2)	C7A—O8	1.368 (2)
O4—H4O	0.9287	O8—C9	1.369 (2)
O5—C12	1.214 (2)	C9—C10	1.350 (3)
C1—C13A	1.393 (2)	C9—H9	0.9500
C1—C2	1.395 (2)	C10—C10A	1.442 (2)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.389 (2)	C10A—C11	1.514 (2)
C2—H2	0.9500	C11—C19	1.524 (2)
C3—C4	1.383 (2)	C11—C11A	1.532 (2)
C3—H3	0.9500	C11—H11	1.0000
C4—C4A	1.398 (2)	C11A—C12	1.506 (2)
C4—H4	0.9500	C11A—H11A	1.0000
C4A—C13A	1.401 (2)	C12—N13	1.389 (2)
C4A—C5	1.473 (2)	N13—C13A	1.408 (2)
C5—N6	1.351 (2)	C14—C15	1.485 (2)
N6—C6A	1.471 (2)	C14—H14A	0.9900
N6—C14	1.477 (2)	C14—H14B	0.9900
C6A—N13	1.467 (2)	C15—C16	1.352 (2)
C6A—C6B	1.541 (2)	C16—C17	1.432 (3)
C6A—H6A	1.0000	C16—H16	0.9500
C6B—C7	1.527 (2)	C17—C18	1.347 (3)
C6B—C11A	1.534 (2)	C17—H17	0.9500
C6B—H6B	1.0000	C18—H18	0.9500

C18—O2—C15	106.38 (14)	C9—C10—C10A	106.03 (15)
C19—O4—H4O	108.4	C9—C10—H10	127.0
C13A—C1—C2	118.66 (15)	C10A—C10—H10	127.0
C13A—C1—H1	120.7	C7A—C10A—C10	105.85 (15)
C2—C1—H1	120.7	C7A—C10A—C11	122.43 (15)
C3—C2—C1	121.48 (16)	C10—C10A—C11	131.71 (15)
C3—C2—H2	119.3	C10A—C11—C19	111.01 (13)
C1—C2—H2	119.3	C10A—C11—C11A	106.54 (13)
C4—C3—C2	119.64 (15)	C19—C11—C11A	111.52 (13)
C4—C3—H3	120.2	C10A—C11—H11	109.2
C2—C3—H3	120.2	C19—C11—H11	109.2
C3—C4—C4A	119.95 (15)	C11A—C11—H11	109.2
C3—C4—H4	120.0	C12—C11A—C11	117.25 (13)
C4A—C4—H4	120.0	C12—C11A—C6B	104.73 (12)
C4—C4A—C13A	119.98 (15)	C11—C11A—C6B	112.60 (13)
C4—C4A—C5	119.23 (14)	C12—C11A—H11A	107.3
C13A—C4A—C5	120.79 (14)	C11—C11A—H11A	107.3
O1—C5—N6	120.60 (15)	C6B—C11A—H11A	107.3
O1—C5—C4A	121.65 (15)	O5—C12—N13	126.00 (15)
N6—C5—C4A	117.73 (14)	O5—C12—C11A	127.11 (14)
C5—N6—C6A	122.48 (14)	N13—C12—C11A	106.78 (13)
C5—N6—C14	116.74 (13)	C12—N13—C13A	127.06 (14)
C6A—N6—C14	118.00 (13)	C12—N13—C6A	113.46 (13)
N13—C6A—N6	109.94 (12)	C13A—N13—C6A	119.47 (13)
N13—C6A—C6B	102.57 (12)	C1—C13A—C4A	120.24 (15)
N6—C6A—C6B	112.07 (13)	C1—C13A—N13	123.27 (14)
N13—C6A—H6A	110.7	C4A—C13A—N13	116.46 (14)
N6—C6A—H6A	110.7	N6—C14—C15	110.51 (13)
C6B—C6A—H6A	110.7	N6—C14—H14A	109.5
C7—C6B—C11A	108.73 (13)	C15—C14—H14A	109.5
C7—C6B—C6A	121.09 (13)	N6—C14—H14B	109.5
C11A—C6B—C6A	103.19 (12)	C15—C14—H14B	109.5
C7—C6B—H6B	107.7	H14A—C14—H14B	108.1
C11A—C6B—H6B	107.7	C16—C15—O2	110.11 (15)
C6A—C6B—H6B	107.7	C16—C15—C14	134.38 (16)
C7A—C7—C6B	103.64 (13)	O2—C15—C14	115.31 (14)
C7A—C7—H7A	111.0	C15—C16—C17	106.55 (16)
C6B—C7—H7A	111.0	C15—C16—H16	126.7
C7A—C7—H7B	111.0	C17—C16—H16	126.7
C6B—C7—H7B	111.0	C18—C17—C16	106.50 (16)
H7A—C7—H7B	109.0	C18—C17—H17	126.8
C10A—C7A—O8	111.01 (15)	C16—C17—H17	126.8
C10A—C7A—C7	129.18 (15)	C17—C18—O2	110.46 (16)
O8—C7A—C7	119.72 (15)	C17—C18—H18	124.8
C7A—O8—C9	105.95 (13)	O2—C18—H18	124.8
C10—C9—O8	111.16 (15)	O3—C19—O4	123.18 (15)
C10—C9—H9	124.4	O3—C19—C11	124.47 (15)
O8—C9—H9	124.4	O4—C19—C11	112.35 (14)

C13A—C1—C2—C3	−0.5 (2)	C19—C11—C11A—C6B	−76.15 (17)
C1—C2—C3—C4	1.6 (3)	C7—C6B—C11A—C12	158.92 (12)
C2—C3—C4—C4A	−0.8 (2)	C6A—C6B—C11A—C12	29.17 (15)
C3—C4—C4A—C13A	−1.1 (2)	C7—C6B—C11A—C11	−72.59 (16)
C3—C4—C4A—C5	179.25 (15)	C6A—C6B—C11A—C11	157.66 (13)
C4—C4A—C5—O1	−11.2 (2)	C11—C11A—C12—O5	39.4 (2)
C13A—C4A—C5—O1	169.16 (15)	C6B—C11A—C12—O5	165.06 (16)
C4—C4A—C5—N6	166.94 (14)	C11—C11A—C12—N13	−144.36 (13)
C13A—C4A—C5—N6	−12.7 (2)	C6B—C11A—C12—N13	−18.74 (16)
O1—C5—N6—C6A	174.40 (14)	O5—C12—N13—C13A	−3.1 (3)
C4A—C5—N6—C6A	−3.8 (2)	C11A—C12—N13—C13A	−179.33 (14)
O1—C5—N6—C14	13.7 (2)	O5—C12—N13—C6A	176.28 (15)
C4A—C5—N6—C14	−164.46 (13)	C11A—C12—N13—C6A	0.03 (17)
C5—N6—C6A—N13	29.51 (19)	N6—C6A—N13—C12	137.81 (13)
C14—N6—C6A—N13	−170.02 (13)	C6B—C6A—N13—C12	18.44 (16)
C5—N6—C6A—C6B	142.89 (15)	N6—C6A—N13—C13A	−42.78 (18)
C14—N6—C6A—C6B	−56.63 (17)	C6B—C6A—N13—C13A	−162.15 (13)
N13—C6A—C6B—C7	−150.21 (14)	C2—C1—C13A—C4A	−1.4 (2)
N6—C6A—C6B—C7	91.92 (17)	C2—C1—C13A—N13	−179.33 (15)
N13—C6A—C6B—C11A	−28.44 (15)	C4—C4A—C13A—C1	2.2 (2)
N6—C6A—C6B—C11A	−146.31 (13)	C5—C4A—C13A—C1	−178.11 (14)
C11A—C6B—C7—C7A	53.19 (16)	C4—C4A—C13A—N13	−179.72 (14)
C6A—C6B—C7—C7A	172.26 (13)	C5—C4A—C13A—N13	−0.1 (2)
C6B—C7—C7A—C10A	−20.2 (2)	C12—N13—C13A—C1	26.6 (2)
C6B—C7—C7A—O8	156.02 (14)	C6A—N13—C13A—C1	−152.68 (15)
C10A—C7A—O8—C9	0.07 (18)	C12—N13—C13A—C4A	−151.33 (15)
C7—C7A—O8—C9	−176.82 (14)	C6A—N13—C13A—C4A	29.3 (2)
C7A—O8—C9—C10	−0.28 (19)	C5—N6—C14—C15	74.64 (18)
O8—C9—C10—C10A	0.37 (19)	C6A—N6—C14—C15	−86.95 (16)
O8—C7A—C10A—C10	0.14 (18)	C18—O2—C15—C16	0.29 (19)
C7—C7A—C10A—C10	176.67 (16)	C18—O2—C15—C14	−175.39 (15)
O8—C7A—C10A—C11	−178.89 (14)	N6—C14—C15—C16	−105.4 (2)
C7—C7A—C10A—C11	−2.4 (3)	N6—C14—C15—O2	68.88 (18)
C9—C10—C10A—C7A	−0.31 (19)	O2—C15—C16—C17	0.04 (19)
C9—C10—C10A—C11	178.60 (16)	C14—C15—C16—C17	174.57 (18)
C7A—C10A—C11—C19	112.13 (17)	C15—C16—C17—C18	−0.4 (2)
C10—C10A—C11—C19	−66.6 (2)	C16—C17—C18—O2	0.6 (2)
C7A—C10A—C11—C11A	−9.5 (2)	C15—O2—C18—C17	−0.5 (2)
C10—C10A—C11—C11A	171.78 (16)	C10A—C11—C19—O3	−109.14 (18)
C10A—C11—C11A—C12	166.74 (13)	C11A—C11—C19—O3	9.5 (2)
C19—C11—C11A—C12	45.47 (18)	C10A—C11—C19—O4	69.78 (18)
C10A—C11—C11A—C6B	45.13 (17)	C11A—C11—C19—O4	−171.58 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1ⁱ	0.93	1.75	2.671 (2)	174
C2—H2···O3ⁱⁱ	0.95	2.42	3.326 (2)	160
C3—H3···O3ⁱⁱⁱ	0.95	2.56	3.384 (2)	146
C7—H7B···O4^iv	0.99	2.54	3.455 (2)	155
C11A—H11A···O1^v	1.00	2.38	3.325 (2)	157

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈N₂O₆
M_r	418.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.2364 (5), 16.9882 (10), 13.1568 (8)
β (°)	99.102 (1)
V (Å³)	1817.74 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.967, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	21001, 5293, 4139
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.160, 1.00
No. of reflections	5293
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.34

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1ⁱ	0.93	1.75	2.671 (2)	174
C2—H2···O3ⁱⁱ	0.95	2.42	3.326 (2)	160
C3—H3···O3ⁱⁱⁱ	0.95	2.56	3.384 (2)	146
C7—H7B···O4^iv	0.99	2.54	3.455 (2)	155
C11A—H11A···O1^v	1.00	2.38	3.325 (2)	157

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Russian Foundation for Basic Research for the financial support of this work (grant No. 11-03-90416-Ukraine).

References

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Volume 67| Part 11| November 2011| Pages o3031-o3032

doi:10.1107/S160053681104311X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(6aS*,6bS*,11R*,11aR*)-6-(2-Furyl­methyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octa­hydro­furo[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carb­­oxy­lic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(6aS,6bS,11R,11aR)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid