(6aS*,6bS*,11R*,11aR*)-6-(2-Furyl-methyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octa-hydro-furo[3',2':5,6]isoindolo[2,1-a]quinazoline-11-carb-oxy-lic acid.

The title compound, C(23)H(18)N(2)O(6), is the product of an intra-molecular thermal cyclo-addition within 1-malein-2-[(E)-2-(2-fur-yl)vin-yl]-4-oxo-3,4-dihydro-quinazoline. The mol-ecule comprises a previously unknown fused penta-cyclic system containing two five-membered rings (2-pyrrolidinone and furan) and three six-membered rings (benzene, 2,3-dihydro-4-pyrimidinone and dihydro-cyclo-hexa-ne). The central five-membered pyrrolidinone ring has the usual envelope conformation. The six-membered dihydro-pyrimidinone and dihydro-cyclo-hexane 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 mol-ecules into centrosymmetric dimers. Weak C-H⋯O hydrogen bonds consolidate further the crystal packing, which exhibits π-π inter-actions, with a short distance of 3.556 (3) Å between the centroids of benzene rings of neighbouring mol-ecules.

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 = 418.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.160

S = 1.00

5293 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.34 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104311X/cv5175sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681104311X/cv5175Isup3.cml

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

C23H18N2O6	F(000) = 872
Mr = 418.39	Dx = 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

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

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(Fo2) + (0.08P)2 + 1.9P] where P = (Fo2 + 2Fc2)/3
5293 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O4iv	0.99	2.54	3.455 (2)	155
C11A—H11A···O1v	1.00	2.38	3.325 (2)	157

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⋯O4iv	0.99	2.54	3.455 (2)	155
C11A—H11A⋯O1v	1.00	2.38	3.325 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .