Methyl 11,2,3,3a-5a-hydr­oxy-1-methyl-10-oxo-4-phenyl 10H-indeno[1,2-b]furo[3,4-b]pyrrole-3a-carboxyl­ate

In the title compound, C₂₂H₂₁NO₅, the pyrrolidine ring and the five-membered ring in the indene group have envelope conformations, while the furan ring adopts a twist conformation. Weak inter­molecular C—H...O inter­actions link the mol­ecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.131
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Highly substituted pyrrolidines have attracted much interest in the past few years, since they constitute the main structural element of many alkaloids and pharmacologically active compounds (Subramaniyan & Raghunathan, 2001). Pyrrolidine derivatives inhibit α-mannosidase activity and growth of human glioblastoma and melanoma cells (Fiaux et al., 2005). These derivatives also exhibit anti-influenza virus activity (Stylianakis et al., 2003). Furan derivatives can promote immune activity, inhibit immune activity and blood platelet aggregation (Li et al., 2005). In view of its medicinal importance, the crystal structure determination of the title compound, (I), was carried out by X-ray diffraction.

A displacement ellipsoid plot of (I) is shown in Fig. 1. It consists of four fused rings, viz. pyrrolidine (A), furan (B), indene (rings C and D) and phenyl (E), and a methoxycarbonyl group. The bond lengths in the pyrrolidine ring are comparable with those observed in related structures (Abdul Ajees et al., 2002; Selvanayagam et al., 2004). The sum of the angles around atom N1 [344.3 (2)°] is in accordance with sp³-hybridization.

The methoxy carbonyl group (C15/O4/O5/C16) is planar, with a maximum deviation of 0.006 (1) Å for atom O5. The C—O bond of the ester group is in a syn orientation. The torsion angle C16—O5—C15—O4 is 2.8 (2)°. The methoxy carbonyl group and phenyl ring E make a dihedral angle of 76.8 (1)°.

Ring A adopts an envelope conformation, with puckering parameters q₂ = 0.362 (2) Å and ϕ = −59.6 (2)° (Cremer & Pople, 1975). Atom C3 deviates by −0.521 (1) Å from the least-squares plane N1/C1/C2/C4. Ring B adopts a twist conformation, with puckering parameters q₂ = 0.517 (2) Å and ϕ = −121.2 (2)°, and displacement asymmetry parameters Δ_S(C13) = 0.086 (1) and Δ₂(C14) = 0.032 (1) (Nardelli, 1983).

The five-membered ring of the indene moiety adopts an envelope conformation, with puckering parameters q₂ = 0.196 (2) Å and ϕ = 170.0 (3)°. Atom C6 deviates by −0.118 (1) Å from the least-squares plane C1/C7/C12/C14. The dihedral angle between the fused six- and five-membered rings (C and D) of the indene moiety is 4.6 (1)°.

An intramolecular O—H···N hydrogen bond is observed in (I) (Table 2). Weak intermolecular C—H···O interactions (Table 2) link the molecules into centrosymmetric dimers. The crystal packing (Fig. 2) is further stabilized by van der Waals forces.

S2. Experimental

To a refluxing solution of ninhydrin (1 mmol) and sarcosine (1 mmol) in methanol was added methyl 3-hydroxy-α-methylene-3-phenylpropanate (1 mmol). The completion of the reaction was monitored by thin-layer chromatography and the solvent was evaporated under reduced pressure. The crude products were purified by column chromatography and eluted with a hexane–ethyl acetate (9:1) mixture to afford the title compound. The compound was recrystallized from a hexane–ethyl acetate (1:1) mixture as diffraction quality crystals.

S3. Refinement

The H atoms were positioned geometrically and treated as riding on their parent C atoms, with C—H = 0.93–0.98 Å, O—H = 0.82 Å and U_iso(H) = 1.5U_eq(C) for methyl H and 1.2U_eq(C or O) for the other H atoms.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular packing of (I), viewed approximately down the a axis. Dashed lines denote O—H···N and C—H···O hydrogen bonds.

Methyl 11,2,3,3a-5a-hydroxy-1-methyl-10-oxo-4-phenyl 10H-indeno[1,2-b]furo[3,4-b]pyrrole-3a-carboxylate

Crystal data

C22H21NO5	Z = 2
Mr = 379.40	F(000) = 400
Triclinic, P1	Dx = 1.324 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6216 (5) Å	Cell parameters from 5288 reflections
b = 10.3055 (6) Å	θ = 2.5–26.5°
c = 11.7758 (6) Å	µ = 0.09 mm^−1
α = 79.462 (1)°	T = 293 K
β = 79.377 (1)°	Block, colourless
γ = 68.876 (1)°	0.24 × 0.22 × 0.19 mm
V = 951.48 (9) Å^3

Data collection

CCD Area Detector diffractometer	3820 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −11→11
10895 measured reflections	k = −13→13
4331 independent reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.077P)^2 + 0.1473P] where P = (Fo^2 + 2Fc^2)/3
4331 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.33283 (14)	0.84122 (12)	0.44108 (9)	0.0475 (3)
O1	−0.01217 (10)	0.93957 (8)	0.31743 (7)	0.0426 (2)
O2	0.02620 (12)	0.83333 (10)	0.50233 (8)	0.0505 (2)
H2	0.0818	0.8709	0.5253	0.076*
O3	0.50446 (12)	0.58998 (10)	0.30407 (10)	0.0593 (3)
O4	0.53542 (14)	0.89342 (14)	0.13066 (11)	0.0728 (3)
O5	0.37918 (12)	0.78388 (10)	0.08512 (8)	0.0528 (2)
C1	0.27034 (14)	0.80094 (12)	0.35086 (10)	0.0378 (2)
C2	0.26760 (13)	0.91560 (11)	0.24361 (9)	0.0354 (2)
C3	0.28825 (16)	1.03305 (13)	0.29631 (11)	0.0446 (3)
H3A	0.3437	1.0875	0.2385	0.054*
H3B	0.1803	1.0952	0.3274	0.054*
C4	0.39500 (19)	0.95659 (16)	0.39218 (13)	0.0559 (3)
H4A	0.5128	0.9219	0.3613	0.067*
H4B	0.3802	1.0171	0.4503	0.067*
C5	0.4357 (2)	0.73189 (18)	0.52009 (13)	0.0632 (4)
H5A	0.3808	0.6646	0.5519	0.095*
H5B	0.4512	0.7730	0.5821	0.095*
H5C	0.5428	0.6861	0.4783	0.095*
C6	0.35457 (15)	0.64900 (12)	0.32243 (11)	0.0433 (3)
C7	0.22171 (16)	0.59118 (12)	0.32277 (11)	0.0448 (3)
C8	0.2363 (2)	0.46259 (14)	0.29157 (13)	0.0579 (4)
H8	0.3407	0.3993	0.2677	0.070*
C9	0.0926 (2)	0.43207 (16)	0.29708 (16)	0.0685 (4)
H9	0.0996	0.3470	0.2765	0.082*
C10	−0.0630 (2)	0.52626 (18)	0.33287 (16)	0.0679 (4)
H10	−0.1587	0.5030	0.3366	0.081*
C11	−0.07835 (19)	0.65410 (16)	0.36308 (13)	0.0555 (3)
H11	−0.1831	0.7175	0.3861	0.067*
C12	0.06611 (15)	0.68548 (12)	0.35822 (10)	0.0423 (3)
C13	0.08061 (14)	0.81680 (12)	0.38647 (10)	0.0392 (3)
C14	0.09009 (13)	0.95232 (11)	0.20878 (10)	0.0364 (2)
H14	0.0918	0.8826	0.1616	0.044*
C15	0.41024 (15)	0.86508 (13)	0.14744 (11)	0.0426 (3)
C16	0.5120 (2)	0.7237 (2)	−0.00405 (17)	0.0811 (5)
H16A	0.4775	0.6674	−0.0439	0.122*
H16B	0.6106	0.6663	0.0311	0.122*
H16C	0.5363	0.7975	−0.0587	0.122*
C17	0.02073 (14)	1.09719 (12)	0.14414 (10)	0.0393 (3)
C18	−0.11627 (18)	1.19970 (14)	0.19292 (12)	0.0524 (3)
H18	−0.1690	1.1794	0.2669	0.063*
C19	−0.1755 (2)	1.33300 (16)	0.13187 (15)	0.0648 (4)
H19	−0.2678	1.4015	0.1650	0.078*
C20	−0.0979 (2)	1.36381 (16)	0.02252 (15)	0.0645 (4)
H20	−0.1372	1.4532	−0.0180	0.077*
C21	0.0376 (2)	1.26252 (17)	−0.02670 (14)	0.0643 (4)
H21	0.0901	1.2834	−0.1006	0.077*
C22	0.09664 (18)	1.12907 (15)	0.03351 (12)	0.0531 (3)
H22	0.1878	1.0606	−0.0007	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0484 (6)	0.0509 (6)	0.0427 (5)	−0.0151 (5)	−0.0139 (4)	−0.0001 (4)
O1	0.0324 (4)	0.0374 (4)	0.0490 (5)	−0.0078 (3)	0.0007 (3)	0.0022 (3)
O2	0.0524 (5)	0.0540 (5)	0.0412 (5)	−0.0189 (4)	0.0075 (4)	−0.0077 (4)
O3	0.0404 (5)	0.0477 (5)	0.0735 (7)	−0.0013 (4)	−0.0008 (4)	−0.0022 (5)
O4	0.0491 (6)	0.0902 (8)	0.0844 (8)	−0.0360 (6)	0.0190 (5)	−0.0261 (6)
O5	0.0493 (5)	0.0563 (6)	0.0494 (5)	−0.0144 (4)	0.0053 (4)	−0.0172 (4)
C1	0.0345 (5)	0.0359 (5)	0.0385 (5)	−0.0098 (4)	−0.0029 (4)	−0.0001 (4)
C2	0.0329 (5)	0.0339 (5)	0.0372 (5)	−0.0110 (4)	−0.0027 (4)	−0.0010 (4)
C3	0.0474 (6)	0.0411 (6)	0.0486 (6)	−0.0191 (5)	−0.0073 (5)	−0.0041 (5)
C4	0.0586 (8)	0.0582 (8)	0.0599 (8)	−0.0264 (7)	−0.0200 (6)	−0.0038 (6)
C5	0.0577 (8)	0.0726 (10)	0.0520 (8)	−0.0145 (7)	−0.0198 (6)	0.0078 (7)
C6	0.0415 (6)	0.0366 (6)	0.0418 (6)	−0.0060 (5)	−0.0020 (5)	0.0017 (4)
C7	0.0510 (7)	0.0344 (6)	0.0437 (6)	−0.0117 (5)	−0.0055 (5)	0.0021 (5)
C8	0.0692 (9)	0.0370 (6)	0.0614 (8)	−0.0111 (6)	−0.0115 (7)	−0.0020 (6)
C9	0.0902 (12)	0.0430 (7)	0.0800 (11)	−0.0299 (8)	−0.0222 (9)	−0.0002 (7)
C10	0.0745 (10)	0.0596 (9)	0.0819 (11)	−0.0411 (8)	−0.0164 (9)	0.0054 (8)
C11	0.0511 (7)	0.0535 (8)	0.0622 (8)	−0.0248 (6)	−0.0023 (6)	0.0018 (6)
C12	0.0452 (6)	0.0376 (6)	0.0409 (6)	−0.0160 (5)	−0.0026 (5)	0.0040 (4)
C13	0.0362 (5)	0.0361 (5)	0.0399 (6)	−0.0106 (4)	0.0006 (4)	−0.0004 (4)
C14	0.0329 (5)	0.0350 (5)	0.0401 (6)	−0.0112 (4)	−0.0040 (4)	−0.0028 (4)
C15	0.0366 (6)	0.0426 (6)	0.0432 (6)	−0.0120 (5)	0.0005 (5)	−0.0011 (5)
C16	0.0754 (11)	0.0878 (13)	0.0702 (11)	−0.0177 (10)	0.0216 (9)	−0.0375 (10)
C17	0.0386 (6)	0.0370 (6)	0.0430 (6)	−0.0121 (4)	−0.0119 (4)	−0.0014 (4)
C18	0.0515 (7)	0.0455 (7)	0.0490 (7)	−0.0035 (5)	−0.0094 (6)	−0.0022 (5)
C19	0.0657 (9)	0.0436 (7)	0.0721 (10)	0.0013 (6)	−0.0198 (8)	−0.0052 (7)
C20	0.0737 (10)	0.0431 (7)	0.0726 (10)	−0.0148 (7)	−0.0293 (8)	0.0128 (7)
C21	0.0702 (10)	0.0620 (9)	0.0556 (8)	−0.0253 (8)	−0.0133 (7)	0.0162 (7)
C22	0.0519 (7)	0.0499 (7)	0.0493 (7)	−0.0129 (6)	−0.0050 (6)	0.0033 (6)

Geometric parameters (Å, º)

N1—C5	1.457 (2)	C7—C8	1.3956 (19)
N1—C1	1.458 (2)	C8—C9	1.372 (2)
N1—C4	1.459 (2)	C8—H8	0.9300
O1—C13	1.4268 (13)	C9—C10	1.386 (3)
O1—C14	1.4275 (13)	C9—H9	0.9300
O2—C13	1.3791 (14)	C10—C11	1.381 (2)
O2—H2	0.8200	C10—H10	0.9300
O3—C6	1.2105 (15)	C11—C12	1.3843 (19)
O4—C15	1.1902 (16)	C11—H11	0.9300
O5—C15	1.3300 (16)	C12—C13	1.5032 (17)
O5—C16	1.4428 (17)	C14—C17	1.5081 (15)
C1—C6	1.5407 (16)	C14—H14	0.9800
C1—C2	1.561 (2)	C16—H16A	0.9600
C1—C13	1.5678 (16)	C16—H16B	0.9600
C2—C15	1.5188 (16)	C16—H16C	0.9600
C2—C3	1.534 (2)	C17—C18	1.3833 (18)
C2—C14	1.5528 (15)	C17—C22	1.3847 (18)
C3—C4	1.509 (2)	C18—C19	1.3904 (19)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—C20	1.376 (2)
C4—H4A	0.9700	C19—H19	0.9300
C4—H4B	0.9700	C20—C21	1.372 (3)
C5—H5A	0.9600	C20—H20	0.9300
C5—H5B	0.9600	C21—C22	1.3874 (19)
C5—H5C	0.9600	C21—H21	0.9300
C6—C7	1.4685 (19)	C22—H22	0.9300
C7—C12	1.3859 (18)
C5—N1—C1	119.0 (1)	C11—C10—C9	121.10 (15)
C5—N1—C4	115.6 (1)	C11—C10—H10	119.4
C1—N1—C4	109.7 (1)	C9—C10—H10	119.4
C13—O1—C14	107.32 (8)	C10—C11—C12	118.33 (14)
C13—O2—H2	109.5	C10—C11—H11	120.8
C15—O5—C16	115.89 (12)	C12—C11—H11	120.8
N1—C1—C6	117.31 (10)	C11—C12—C7	120.58 (12)
N1—C1—C2	106.19 (9)	C11—C12—C13	127.85 (12)
C6—C1—C2	114.57 (9)	C7—C12—C13	111.56 (11)
N1—C1—C13	110.39 (9)	O2—C13—O1	108.43 (9)
C6—C1—C13	104.17 (9)	O2—C13—C12	111.36 (9)
C2—C1—C13	103.32 (8)	O1—C13—C12	112.38 (10)
C15—C2—C3	110.54 (9)	O2—C13—C1	113.02 (10)
C15—C2—C14	114.35 (9)	O1—C13—C1	106.56 (8)
C3—C2—C14	113.47 (9)	C12—C13—C1	105.03 (9)
C15—C2—C1	112.53 (9)	O1—C14—C17	110.06 (9)
C3—C2—C1	102.50 (9)	O1—C14—C2	103.86 (8)
C14—C2—C1	102.59 (8)	C17—C14—C2	114.81 (9)
C4—C3—C2	104.12 (10)	O1—C14—H14	109.3
C4—C3—H3A	110.9	C17—C14—H14	109.3
C2—C3—H3A	110.9	C2—C14—H14	109.3
C4—C3—H3B	110.9	O4—C15—O5	124.09 (12)
C2—C3—H3B	110.9	O4—C15—C2	124.12 (12)
H3A—C3—H3B	109.0	O5—C15—C2	111.78 (10)
N1—C4—C3	103.37 (10)	O5—C16—H16A	109.5
N1—C4—H4A	111.1	O5—C16—H16B	109.5
C3—C4—H4A	111.1	H16A—C16—H16B	109.5
N1—C4—H4B	111.1	O5—C16—H16C	109.5
C3—C4—H4B	111.1	H16A—C16—H16C	109.5
H4A—C4—H4B	109.1	H16B—C16—H16C	109.5
N1—C5—H5A	109.5	C18—C17—C22	119.02 (12)
N1—C5—H5B	109.5	C18—C17—C14	121.67 (11)
H5A—C5—H5B	109.5	C22—C17—C14	119.31 (11)
N1—C5—H5C	109.5	C17—C18—C19	120.30 (14)
H5A—C5—H5C	109.5	C17—C18—H18	119.8
H5B—C5—H5C	109.5	C19—C18—H18	119.8
O3—C6—C7	127.23 (12)	C20—C19—C18	120.13 (15)
O3—C6—C1	124.83 (12)	C20—C19—H19	119.9
C7—C6—C1	107.94 (10)	C18—C19—H19	119.9
C12—C7—C8	120.84 (13)	C21—C20—C19	119.93 (13)
C12—C7—C6	110.49 (11)	C21—C20—H20	120.0
C8—C7—C6	128.66 (13)	C19—C20—H20	120.0
C9—C8—C7	118.20 (15)	C20—C21—C22	120.19 (14)
C9—C8—H8	120.9	C20—C21—H21	119.9
C7—C8—H8	120.9	C22—C21—H21	119.9
C8—C9—C10	120.94 (14)	C17—C22—C21	120.43 (14)
C8—C9—H9	119.5	C17—C22—H22	119.8
C10—C9—H9	119.5	C21—C22—H22	119.8
C5—N1—C1—C6	−16.33 (16)	C14—O1—C13—C1	31.46 (11)
C4—N1—C1—C6	120.05 (12)	C11—C12—C13—O2	64.01 (16)
C5—N1—C1—C2	−145.93 (11)	C7—C12—C13—O2	−116.71 (11)
C4—N1—C1—C2	−9.54 (13)	C11—C12—C13—O1	−57.86 (16)
C5—N1—C1—C13	102.74 (13)	C7—C12—C13—O1	121.41 (11)
C4—N1—C1—C13	−120.88 (11)	C11—C12—C13—C1	−173.31 (12)
N1—C1—C2—C15	104.64 (11)	C7—C12—C13—C1	5.96 (13)
C6—C1—C2—C15	−26.52 (14)	N1—C1—C13—O2	−13.78 (13)
C13—C1—C2—C15	−139.16 (10)	C6—C1—C13—O2	113.00 (10)
N1—C1—C2—C3	−14.12 (11)	C2—C1—C13—O2	−126.96 (10)
C6—C1—C2—C3	−145.27 (10)	N1—C1—C13—O1	105.21 (10)
C13—C1—C2—C3	102.08 (10)	C6—C1—C13—O1	−128.01 (9)
N1—C1—C2—C14	−131.99 (9)	C2—C1—C13—O1	−7.97 (11)
C6—C1—C2—C14	96.85 (11)	N1—C1—C13—C12	−135.37 (10)
C13—C1—C2—C14	−15.79 (11)	C6—C1—C13—C12	−8.59 (11)
C15—C2—C3—C4	−88.43 (12)	C2—C1—C13—C12	111.45 (10)
C14—C2—C3—C4	141.57 (11)	C13—O1—C14—C17	−165.37 (9)
C1—C2—C3—C4	31.71 (12)	C13—O1—C14—C2	−41.98 (11)
C5—N1—C4—C3	167.76 (12)	C15—C2—C14—O1	156.91 (9)
C1—N1—C4—C3	29.75 (14)	C3—C2—C14—O1	−75.04 (11)
C2—C3—C4—N1	−38.00 (13)	C1—C2—C14—O1	34.76 (10)
N1—C1—C6—O3	−48.73 (17)	C15—C2—C14—C17	−82.87 (12)
C2—C1—C6—O3	76.80 (15)	C3—C2—C14—C17	45.19 (13)
C13—C1—C6—O3	−171.07 (12)	C1—C2—C14—C17	154.99 (9)
N1—C1—C6—C7	130.88 (11)	C16—O5—C15—O4	2.8 (2)
C2—C1—C6—C7	−103.59 (11)	C16—O5—C15—C2	−176.40 (13)
C13—C1—C6—C7	8.55 (12)	C3—C2—C15—O4	13.12 (18)
O3—C6—C7—C12	174.30 (13)	C14—C2—C15—O4	142.65 (13)
C1—C6—C7—C12	−5.30 (14)	C1—C2—C15—O4	−100.81 (15)
O3—C6—C7—C8	−6.8 (2)	C3—C2—C15—O5	−167.65 (10)
C1—C6—C7—C8	173.60 (13)	C14—C2—C15—O5	−38.12 (13)
C12—C7—C8—C9	−0.1 (2)	C1—C2—C15—O5	78.42 (12)
C6—C7—C8—C9	−178.86 (13)	O1—C14—C17—C18	3.95 (16)
C7—C8—C9—C10	−0.1 (2)	C2—C14—C17—C18	−112.79 (13)
C8—C9—C10—C11	0.6 (3)	O1—C14—C17—C22	−176.57 (11)
C9—C10—C11—C12	−0.8 (2)	C2—C14—C17—C22	66.69 (14)
C10—C11—C12—C7	0.6 (2)	C22—C17—C18—C19	−0.6 (2)
C10—C11—C12—C13	179.86 (13)	C14—C17—C18—C19	178.91 (13)
C8—C7—C12—C11	−0.2 (2)	C17—C18—C19—C20	−0.1 (2)
C6—C7—C12—C11	178.80 (11)	C18—C19—C20—C21	0.4 (3)
C8—C7—C12—C13	−179.53 (12)	C19—C20—C21—C22	0.0 (3)
C6—C7—C12—C13	−0.54 (14)	C18—C17—C22—C21	1.0 (2)
C14—O1—C13—O2	153.40 (9)	C14—C17—C22—C21	−178.51 (13)
C14—O1—C13—C12	−83.06 (11)	C20—C21—C22—C17	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2^i	0.97	2.45	3.317 (2)	148
O2—H2···N1	0.82	2.15	2.636 (2)	118

Symmetry code: (i) −x, −y+2, −z+1.