A diastereomer of methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro-[ace-naphthyl-ene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

In the title compound, C26H22N2O4, the central pyrrolidine ring adopts a twist conformation and the cyclo-pentane ring of the dihydro-acenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydro-acenaphthyl-ene group forms dihedral angles of 83.4 (9) and 61.3 (7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds. The title compound is a diastereomer of a previously reported structure.

Related literature

For background literature and the previously reported diastereomer, see: Ganesh et al. (2013 ▶). For a related structure, see: Wei et al. (2012 ▶). For information on ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H22N2O4

M = 426.46

Orthorhombic,

a = 27.2997 (15) Å

b = 9.7923 (6) Å

c = 15.8557 (10) Å

V = 4238.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.978, T max = 0.983

23813 measured reflections

5039 independent reflections

3022 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.02

5039 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004868/bt6885sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004868/bt6885Isup2.hkl

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

C26H22N2O4	F(000) = 1792
Mr = 426.46	Dx = 1.337 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5039 reflections
a = 27.2997 (15) Å	θ = 1.5–27.9°
b = 9.7923 (6) Å	µ = 0.09 mm−1
c = 15.8557 (10) Å	T = 293 K
V = 4238.7 (4) Å3	Block, colourless
Z = 8	0.25 × 0.22 × 0.19 mm

Bruker APEXII CCD area-detector diffractometer	5039 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −35→31
Tmin = 0.978, Tmax = 0.983	k = −12→11
23813 measured reflections	l = −18→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0531P)2 + 1.3523P] where P = (Fo2 + 2Fc2)/3
5039 reflections	(Δ/σ)max = 0.002
292 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.55248 (7)	−0.08437 (18)	0.02663 (15)	0.0583 (6)
H1A	0.5740	−0.1607	0.0354	0.087*
H1B	0.5527	−0.0596	−0.0320	0.087*
H1C	0.5198	−0.1088	0.0432	0.087*
C2	0.57113 (7)	0.0054 (2)	0.16787 (14)	0.0543 (5)
H2A	0.5784	−0.0897	0.1794	0.065*
H2B	0.5402	0.0285	0.1943	0.065*
C3	0.61210 (7)	0.09760 (19)	0.20075 (12)	0.0463 (5)
H3	0.6412	0.0409	0.2098	0.056*
C4	0.62250 (6)	0.19357 (17)	0.12618 (11)	0.0380 (4)
C5	0.61516 (6)	0.09285 (16)	0.05178 (12)	0.0380 (4)
C6	0.65873 (6)	−0.01367 (18)	0.04464 (13)	0.0454 (5)
C7	0.68374 (6)	0.0100 (2)	−0.03587 (13)	0.0492 (5)
C8	0.72342 (7)	−0.0500 (2)	−0.07337 (16)	0.0672 (6)
H8	0.7404	−0.1202	−0.0469	0.081*
C9	0.73756 (9)	−0.0022 (3)	−0.15287 (18)	0.0842 (8)
H9	0.7652	−0.0399	−0.1781	0.101*
C10	0.71257 (9)	0.0973 (3)	−0.19492 (16)	0.0778 (7)
H10	0.7234	0.1258	−0.2477	0.093*
C11	0.67050 (8)	0.1574 (2)	−0.15918 (14)	0.0573 (5)
C12	0.65758 (7)	0.11197 (19)	−0.07840 (12)	0.0444 (4)
C13	0.61607 (6)	0.15884 (17)	−0.03457 (12)	0.0401 (4)
C14	0.58614 (7)	0.24994 (19)	−0.07357 (13)	0.0500 (5)
H14	0.5581	0.2818	−0.0467	0.060*
C15	0.59812 (9)	0.2955 (2)	−0.15527 (14)	0.0617 (6)
H15	0.5773	0.3571	−0.1819	0.074*
C16	0.63878 (9)	0.2529 (2)	−0.19651 (14)	0.0661 (6)
H16	0.6458	0.2872	−0.2499	0.079*
C17	0.67325 (6)	0.26047 (19)	0.12476 (12)	0.0413 (4)
C18	0.61710 (6)	0.43187 (17)	0.11591 (11)	0.0368 (4)
C19	0.58897 (6)	0.31498 (16)	0.12240 (11)	0.0359 (4)
C20	0.53874 (6)	0.32524 (19)	0.12696 (13)	0.0479 (5)
H20	0.5193	0.2477	0.1322	0.058*
C21	0.51788 (7)	0.4538 (2)	0.12360 (16)	0.0627 (6)
H21	0.4840	0.4627	0.1268	0.075*
C22	0.54625 (8)	0.5680 (2)	0.11568 (16)	0.0644 (6)
H22	0.5313	0.6532	0.1132	0.077*
C23	0.59676 (7)	0.55977 (19)	0.11128 (13)	0.0501 (5)
H23	0.6161	0.6374	0.1054	0.060*
C24	0.70630 (7)	0.4956 (2)	0.11344 (14)	0.0560 (5)
H24A	0.7370	0.4487	0.1084	0.084*
H24B	0.7060	0.5481	0.1646	0.084*
H24C	0.7020	0.5554	0.0660	0.084*
C25	0.60097 (8)	0.1700 (2)	0.28144 (14)	0.0548 (5)
C26	0.63246 (11)	0.3314 (3)	0.37857 (16)	0.0865 (8)
H26A	0.5988	0.3558	0.3876	0.130*
H26B	0.6520	0.4127	0.3756	0.130*
H26C	0.6436	0.2755	0.4245	0.130*
N1	0.56904 (5)	0.03024 (14)	0.07673 (10)	0.0434 (4)
N2	0.66700 (5)	0.39740 (15)	0.11545 (9)	0.0403 (4)
O1	0.66576 (5)	−0.10603 (14)	0.09387 (10)	0.0617 (4)
O2	0.71209 (5)	0.20188 (14)	0.12955 (10)	0.0625 (4)
O3	0.56571 (6)	0.1529 (2)	0.32417 (11)	0.0878 (6)
O4	0.63683 (6)	0.25647 (16)	0.30058 (10)	0.0693 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0490 (11)	0.0381 (10)	0.0879 (17)	−0.0046 (9)	−0.0040 (11)	0.0022 (10)
C2	0.0531 (12)	0.0480 (11)	0.0617 (14)	−0.0003 (10)	0.0105 (10)	0.0145 (10)
C3	0.0414 (10)	0.0462 (10)	0.0512 (12)	0.0086 (8)	0.0057 (9)	0.0108 (9)
C4	0.0278 (8)	0.0392 (9)	0.0470 (11)	0.0050 (7)	0.0022 (7)	0.0035 (8)
C5	0.0293 (8)	0.0356 (8)	0.0491 (11)	0.0030 (7)	0.0016 (8)	0.0035 (8)
C6	0.0369 (9)	0.0405 (10)	0.0588 (12)	0.0054 (8)	−0.0038 (9)	−0.0033 (9)
C7	0.0354 (9)	0.0547 (11)	0.0576 (13)	0.0022 (9)	−0.0015 (9)	−0.0152 (10)
C8	0.0456 (12)	0.0851 (16)	0.0708 (16)	0.0130 (11)	0.0014 (11)	−0.0249 (13)
C9	0.0501 (14)	0.130 (2)	0.0731 (18)	0.0053 (16)	0.0132 (13)	−0.0356 (18)
C10	0.0615 (15)	0.118 (2)	0.0535 (15)	−0.0135 (15)	0.0146 (12)	−0.0166 (15)
C11	0.0541 (12)	0.0691 (14)	0.0487 (13)	−0.0160 (11)	0.0033 (10)	−0.0122 (11)
C12	0.0383 (10)	0.0490 (10)	0.0460 (11)	−0.0077 (8)	−0.0008 (8)	−0.0098 (9)
C13	0.0346 (9)	0.0391 (9)	0.0465 (11)	−0.0042 (7)	−0.0007 (8)	−0.0018 (8)
C14	0.0522 (11)	0.0468 (10)	0.0510 (12)	0.0023 (9)	−0.0042 (9)	0.0033 (9)
C15	0.0739 (15)	0.0565 (12)	0.0546 (14)	−0.0030 (11)	−0.0114 (12)	0.0076 (10)
C16	0.0824 (16)	0.0717 (15)	0.0443 (13)	−0.0195 (14)	−0.0002 (12)	0.0046 (11)
C17	0.0298 (9)	0.0503 (10)	0.0439 (11)	0.0042 (8)	0.0005 (8)	−0.0039 (8)
C18	0.0312 (9)	0.0406 (9)	0.0388 (10)	0.0001 (7)	−0.0009 (7)	0.0022 (7)
C19	0.0302 (8)	0.0364 (9)	0.0410 (10)	0.0028 (7)	0.0035 (7)	0.0027 (7)
C20	0.0287 (9)	0.0435 (10)	0.0716 (14)	0.0002 (8)	0.0057 (9)	0.0043 (9)
C21	0.0327 (10)	0.0522 (12)	0.1033 (19)	0.0103 (9)	0.0043 (11)	0.0031 (12)
C22	0.0507 (12)	0.0411 (11)	0.1013 (19)	0.0123 (10)	−0.0040 (12)	0.0057 (11)
C23	0.0472 (11)	0.0385 (10)	0.0646 (14)	−0.0027 (8)	−0.0034 (10)	0.0049 (9)
C24	0.0359 (10)	0.0637 (12)	0.0684 (15)	−0.0142 (9)	0.0005 (10)	−0.0036 (11)
C25	0.0512 (12)	0.0612 (13)	0.0522 (13)	0.0139 (10)	0.0039 (10)	0.0137 (10)
C26	0.113 (2)	0.0783 (17)	0.0680 (17)	0.0095 (16)	0.0000 (16)	−0.0145 (14)
N1	0.0343 (8)	0.0364 (8)	0.0595 (10)	−0.0005 (6)	0.0051 (7)	0.0061 (7)
N2	0.0283 (7)	0.0451 (8)	0.0474 (9)	−0.0041 (6)	−0.0004 (6)	0.0007 (7)
O1	0.0559 (9)	0.0494 (8)	0.0797 (11)	0.0188 (7)	0.0000 (8)	0.0083 (8)
O2	0.0301 (7)	0.0664 (9)	0.0908 (12)	0.0120 (6)	−0.0030 (7)	−0.0080 (8)
O3	0.0700 (11)	0.1265 (15)	0.0668 (11)	0.0017 (10)	0.0238 (9)	−0.0047 (11)
O4	0.0766 (11)	0.0749 (10)	0.0566 (10)	−0.0028 (9)	0.0069 (8)	−0.0051 (8)

C1—N1	1.447 (2)	C13—C14	1.359 (2)
C1—H1A	0.9600	C14—C15	1.408 (3)
C1—H1B	0.9600	C14—H14	0.9300
C1—H1C	0.9600	C15—C16	1.354 (3)
C2—N1	1.467 (3)	C15—H15	0.9300
C2—C3	1.529 (3)	C16—H16	0.9300
C2—H2A	0.9700	C17—O2	1.208 (2)
C2—H2B	0.9700	C17—N2	1.360 (2)
C3—C25	1.494 (3)	C18—C23	1.372 (2)
C3—C4	1.537 (2)	C18—C19	1.382 (2)
C3—H3	0.9800	C18—N2	1.403 (2)
C4—C19	1.502 (2)	C19—C20	1.377 (2)
C4—C17	1.533 (2)	C20—C21	1.383 (3)
C4—C5	1.551 (2)	C20—H20	0.9300
C5—N1	1.455 (2)	C21—C22	1.366 (3)
C5—C13	1.514 (2)	C21—H21	0.9300
C5—C6	1.586 (2)	C22—C23	1.383 (3)
C6—O1	1.210 (2)	C22—H22	0.9300
C6—C7	1.466 (3)	C23—H23	0.9300
C7—C8	1.368 (3)	C24—N2	1.441 (2)
C7—C12	1.401 (3)	C24—H24A	0.9600
C8—C9	1.399 (4)	C24—H24B	0.9600
C8—H8	0.9300	C24—H24C	0.9600
C9—C10	1.364 (4)	C25—O3	1.189 (2)
C9—H9	0.9300	C25—O4	1.330 (3)
C10—C11	1.410 (3)	C26—O4	1.443 (3)
C10—H10	0.9300	C26—H26A	0.9600
C11—C12	1.401 (3)	C26—H26B	0.9600
C11—C16	1.406 (3)	C26—H26C	0.9600
C12—C13	1.406 (2)
N1—C1—H1A	109.5	C12—C13—C5	108.70 (15)
N1—C1—H1B	109.5	C13—C14—C15	119.1 (2)
H1A—C1—H1B	109.5	C13—C14—H14	120.4
N1—C1—H1C	109.5	C15—C14—H14	120.4
H1A—C1—H1C	109.5	C16—C15—C14	122.5 (2)
H1B—C1—H1C	109.5	C16—C15—H15	118.8
N1—C2—C3	105.47 (15)	C14—C15—H15	118.8
N1—C2—H2A	110.6	C15—C16—C11	120.4 (2)
C3—C2—H2A	110.6	C15—C16—H16	119.8
N1—C2—H2B	110.6	C11—C16—H16	119.8
C3—C2—H2B	110.6	O2—C17—N2	125.81 (17)
H2A—C2—H2B	108.8	O2—C17—C4	126.13 (17)
C25—C3—C2	115.06 (17)	N2—C17—C4	108.05 (14)
C25—C3—C4	113.98 (16)	C23—C18—C19	122.33 (16)
C2—C3—C4	103.53 (15)	C23—C18—N2	127.75 (16)
C25—C3—H3	108.0	C19—C18—N2	109.91 (14)
C2—C3—H3	108.0	C20—C19—C18	119.80 (15)
C4—C3—H3	108.0	C20—C19—C4	131.52 (15)
C19—C4—C17	102.25 (13)	C18—C19—C4	108.64 (14)
C19—C4—C3	113.70 (14)	C19—C20—C21	118.33 (17)
C17—C4—C3	116.09 (15)	C19—C20—H20	120.8
C19—C4—C5	113.23 (14)	C21—C20—H20	120.8
C17—C4—C5	112.19 (14)	C22—C21—C20	121.03 (18)
C3—C4—C5	99.93 (13)	C22—C21—H21	119.5
N1—C5—C13	116.08 (14)	C20—C21—H21	119.5
N1—C5—C4	99.96 (13)	C21—C22—C23	121.47 (18)
C13—C5—C4	114.48 (13)	C21—C22—H22	119.3
N1—C5—C6	113.03 (13)	C23—C22—H22	119.3
C13—C5—C6	101.76 (14)	C18—C23—C22	117.02 (18)
C4—C5—C6	112.06 (14)	C18—C23—H23	121.5
O1—C6—C7	127.30 (17)	C22—C23—H23	121.5
O1—C6—C5	124.36 (17)	N2—C24—H24A	109.5
C7—C6—C5	107.91 (15)	N2—C24—H24B	109.5
C8—C7—C12	120.0 (2)	H24A—C24—H24B	109.5
C8—C7—C6	132.8 (2)	N2—C24—H24C	109.5
C12—C7—C6	107.11 (16)	H24A—C24—H24C	109.5
C7—C8—C9	117.8 (2)	H24B—C24—H24C	109.5
C7—C8—H8	121.1	O3—C25—O4	123.7 (2)
C9—C8—H8	121.1	O3—C25—C3	125.9 (2)
C10—C9—C8	122.8 (2)	O4—C25—C3	110.38 (17)
C10—C9—H9	118.6	O4—C26—H26A	109.5
C8—C9—H9	118.6	O4—C26—H26B	109.5
C9—C10—C11	120.6 (2)	H26A—C26—H26B	109.5
C9—C10—H10	119.7	O4—C26—H26C	109.5
C11—C10—H10	119.7	H26A—C26—H26C	109.5
C12—C11—C16	116.18 (19)	H26B—C26—H26C	109.5
C12—C11—C10	116.1 (2)	C1—N1—C5	116.59 (15)
C16—C11—C10	127.6 (2)	C1—N1—C2	115.12 (15)
C7—C12—C11	122.55 (18)	C5—N1—C2	107.69 (14)
C7—C12—C13	113.93 (18)	C17—N2—C18	111.00 (14)
C11—C12—C13	123.44 (19)	C17—N2—C24	124.54 (15)
C14—C13—C12	118.29 (18)	C18—N2—C24	124.22 (15)
C14—C13—C5	133.00 (17)	C25—O4—C26	117.31 (19)
N1—C2—C3—C25	137.57 (16)	C12—C13—C14—C15	−1.0 (3)
N1—C2—C3—C4	12.55 (18)	C5—C13—C14—C15	178.08 (18)
C25—C3—C4—C19	−41.3 (2)	C13—C14—C15—C16	−0.7 (3)
C2—C3—C4—C19	84.45 (18)	C14—C15—C16—C11	1.5 (3)
C25—C3—C4—C17	77.0 (2)	C12—C11—C16—C15	−0.6 (3)
C2—C3—C4—C17	−157.33 (15)	C10—C11—C16—C15	176.3 (2)
C25—C3—C4—C5	−162.21 (15)	C19—C4—C17—O2	177.45 (19)
C2—C3—C4—C5	−36.50 (16)	C3—C4—C17—O2	53.1 (3)
C19—C4—C5—N1	−73.87 (16)	C5—C4—C17—O2	−60.9 (2)
C17—C4—C5—N1	171.02 (13)	C19—C4—C17—N2	−3.77 (19)
C3—C4—C5—N1	47.41 (14)	C3—C4—C17—N2	−128.12 (16)
C19—C4—C5—C13	50.91 (19)	C5—C4—C17—N2	117.86 (16)
C17—C4—C5—C13	−64.20 (18)	C23—C18—C19—C20	−2.0 (3)
C3—C4—C5—C13	172.20 (14)	N2—C18—C19—C20	177.74 (17)
C19—C4—C5—C6	166.14 (14)	C23—C18—C19—C4	−179.96 (17)
C17—C4—C5—C6	51.03 (19)	N2—C18—C19—C4	−0.3 (2)
C3—C4—C5—C6	−72.58 (16)	C17—C4—C19—C20	−175.3 (2)
N1—C5—C6—O1	−40.9 (3)	C3—C4—C19—C20	−49.4 (3)
C13—C5—C6—O1	−166.14 (18)	C5—C4—C19—C20	63.8 (3)
C4—C5—C6—O1	71.1 (2)	C17—C4—C19—C18	2.39 (18)
N1—C5—C6—C7	131.98 (16)	C3—C4—C19—C18	128.31 (16)
C13—C5—C6—C7	6.77 (17)	C5—C4—C19—C18	−118.52 (16)
C4—C5—C6—C7	−115.98 (16)	C18—C19—C20—C21	0.9 (3)
O1—C6—C7—C8	−8.3 (4)	C4—C19—C20—C21	178.4 (2)
C5—C6—C7—C8	179.0 (2)	C19—C20—C21—C22	0.2 (3)
O1—C6—C7—C12	168.86 (19)	C20—C21—C22—C23	−0.4 (4)
C5—C6—C7—C12	−3.79 (19)	C19—C18—C23—C22	1.7 (3)
C12—C7—C8—C9	2.4 (3)	N2—C18—C23—C22	−177.93 (19)
C6—C7—C8—C9	179.3 (2)	C21—C22—C23—C18	−0.5 (3)
C7—C8—C9—C10	−2.3 (4)	C2—C3—C25—O3	6.7 (3)
C8—C9—C10—C11	0.0 (4)	C4—C3—C25—O3	126.1 (2)
C9—C10—C11—C12	2.0 (3)	C2—C3—C25—O4	−174.36 (16)
C9—C10—C11—C16	−174.9 (2)	C4—C3—C25—O4	−55.0 (2)
C8—C7—C12—C11	−0.4 (3)	C13—C5—N1—C1	63.6 (2)
C6—C7—C12—C11	−178.03 (17)	C4—C5—N1—C1	−172.74 (14)
C8—C7—C12—C13	176.48 (17)	C6—C5—N1—C1	−53.5 (2)
C6—C7—C12—C13	−1.1 (2)	C13—C5—N1—C2	−165.25 (15)
C16—C11—C12—C7	175.42 (18)	C4—C5—N1—C2	−41.59 (16)
C10—C11—C12—C7	−1.8 (3)	C6—C5—N1—C2	77.70 (18)
C16—C11—C12—C13	−1.2 (3)	C3—C2—N1—C1	150.60 (15)
C10—C11—C12—C13	−178.42 (18)	C3—C2—N1—C5	18.64 (18)
C7—C12—C13—C14	−174.87 (16)	O2—C17—N2—C18	−177.33 (18)
C11—C12—C13—C14	2.0 (3)	C4—C17—N2—C18	3.9 (2)
C7—C12—C13—C5	5.8 (2)	O2—C17—N2—C24	−2.8 (3)
C11—C12—C13—C5	−177.31 (16)	C4—C17—N2—C24	178.40 (16)
N1—C5—C13—C14	50.3 (3)	C23—C18—N2—C17	177.32 (19)
C4—C5—C13—C14	−65.5 (2)	C19—C18—N2—C17	−2.4 (2)
C6—C5—C13—C14	173.43 (19)	C23—C18—N2—C24	2.8 (3)
N1—C5—C13—C12	−130.55 (15)	C19—C18—N2—C24	−176.90 (17)
C4—C5—C13—C12	113.69 (15)	O3—C25—O4—C26	1.0 (3)
C6—C5—C13—C12	−7.40 (17)	C3—C25—O4—C26	−177.94 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O3i	0.96	2.48	3.299 (3)	143
C20—H20···O3ii	0.93	2.59	3.403 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O3i	0.96	2.48	3.299 (3)	143
C20—H20⋯O3ii	0.93	2.59	3.403 (3)	146

Symmetry codes: (i) ; (ii) .