rac-Methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro-[acenaphthyl-ene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

In the title compound, C(26)H(22)N(2)O(4), the pyrrolidine ring adopts a twisted conformation and the other five-membered rings adopt envelope conformations with the spiro C atoms as the flap atoms. The naphthalene ring system of the dihydro-acenaphthyl-ene group forms dihedral angles of 89.2 (9) and 75.5 (6)° with the pyrrolidine and indole rings, respectively. The pyrrolidine ring makes a dihedral angle of 80.1 (9)° with the indole ring. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains along the b-axis direction.

Related literature

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998 ▶); Wright et al. (2000 ▶); Varma et al. (1994 ▶). For a related structure, see: Wei et al. (2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H22N2O4

M = 426.46

Monoclinic,

a = 15.4839 (4) Å

b = 9.5832 (2) Å

c = 15.6375 (4) Å

β = 115.184 (1)°

V = 2099.81 (9) Å3

Z = 4

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 = 0.977, T max = 0.983

19264 measured reflections

4057 independent reflections

3017 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.03

4057 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 (Bruker, 2008 ▶); 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/S1600536813000470/lx2278sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000470/lx2278Isup2.hkl

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

C26H22N2O4	F(000) = 896
Mr = 426.46	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4057 reflections
a = 15.4839 (4) Å	θ = 1.5–25.8°
b = 9.5832 (2) Å	µ = 0.09 mm−1
c = 15.6375 (4) Å	T = 293 K
β = 115.184 (1)°	Block, colourless
V = 2099.81 (9) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4057 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 25.8°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
Tmin = 0.977, Tmax = 0.983	k = −11→11
19264 measured reflections	l = −19→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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.5222P] where P = (Fo2 + 2Fc2)/3
4057 reflections	(Δ/σ)max < 0.001
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
O1	0.69067 (8)	0.37535 (12)	0.28269 (9)	0.0565 (3)
O2	0.87808 (9)	0.87118 (12)	0.39458 (9)	0.0552 (3)
O3	0.64333 (11)	0.58931 (15)	0.48841 (11)	0.0762 (4)
O4	0.65285 (10)	0.81185 (13)	0.45236 (10)	0.0648 (4)
N1	0.87057 (9)	0.51097 (14)	0.41944 (9)	0.0456 (3)
N2	0.73670 (10)	0.90053 (13)	0.26438 (10)	0.0490 (3)
C1	0.91612 (13)	0.37648 (19)	0.42302 (14)	0.0590 (5)
H1A	0.8683	0.3050	0.3999	0.088*
H1B	0.9596	0.3560	0.4871	0.088*
H1C	0.9505	0.3800	0.3844	0.088*
C2	0.81537 (13)	0.51929 (18)	0.47465 (12)	0.0537 (4)
H2A	0.8562	0.5123	0.5418	0.064*
H2B	0.7673	0.4465	0.4568	0.064*
C3	0.77008 (12)	0.66228 (17)	0.44928 (11)	0.0468 (4)
H3	0.8174	0.7303	0.4890	0.056*
C4	0.75428 (11)	0.68832 (15)	0.34492 (11)	0.0385 (3)
C5	0.81077 (10)	0.56359 (15)	0.32472 (10)	0.0377 (3)
C6	0.74144 (11)	0.44844 (15)	0.25997 (12)	0.0410 (4)
C7	0.75797 (10)	0.43438 (15)	0.17441 (11)	0.0399 (4)
C8	0.71903 (12)	0.34921 (17)	0.09679 (12)	0.0503 (4)
H8	0.6677	0.2913	0.0878	0.060*
C9	0.75897 (13)	0.35191 (18)	0.03135 (12)	0.0566 (5)
H9	0.7321	0.2965	−0.0225	0.068*
C10	0.83614 (14)	0.43324 (18)	0.04395 (12)	0.0544 (4)
H10	0.8613	0.4304	−0.0004	0.065*
C11	0.87793 (12)	0.52114 (16)	0.12320 (11)	0.0437 (4)
C12	0.83529 (10)	0.52056 (15)	0.18635 (10)	0.0375 (3)
C13	0.86999 (10)	0.59774 (15)	0.27095 (11)	0.0377 (3)
C14	0.95079 (11)	0.67546 (17)	0.29344 (12)	0.0470 (4)
H14	0.9769	0.7255	0.3497	0.056*
C15	0.99391 (13)	0.67866 (19)	0.23017 (13)	0.0550 (5)
H15	1.0482	0.7331	0.2454	0.066*
C16	0.95951 (13)	0.60548 (19)	0.14783 (13)	0.0545 (4)
H16	0.9898	0.6111	0.1078	0.065*
C17	0.79970 (12)	0.82915 (16)	0.33990 (12)	0.0430 (4)
C18	0.65287 (11)	0.70826 (15)	0.27105 (11)	0.0394 (4)
C19	0.64718 (11)	0.83487 (16)	0.22577 (11)	0.0429 (4)
C20	0.56296 (13)	0.88569 (19)	0.15782 (13)	0.0555 (5)
H20	0.5609	0.9701	0.1276	0.067*
C21	0.48165 (13)	0.8071 (2)	0.13602 (14)	0.0601 (5)
H21	0.4237	0.8390	0.0902	0.072*
C22	0.48497 (12)	0.6824 (2)	0.18089 (14)	0.0584 (5)
H22	0.4292	0.6317	0.1657	0.070*
C23	0.57069 (11)	0.63162 (17)	0.24860 (12)	0.0489 (4)
H23	0.5727	0.5470	0.2785	0.059*
C24	0.75568 (16)	1.03779 (19)	0.23647 (17)	0.0747 (6)
H24A	0.7189	1.1066	0.2511	0.112*
H24B	0.7383	1.0385	0.1698	0.112*
H24C	0.8224	1.0589	0.2701	0.112*
C25	0.68278 (13)	0.68033 (18)	0.46619 (12)	0.0511 (4)
C26	0.56590 (17)	0.8428 (3)	0.4604 (2)	0.0891 (8)
H26A	0.5144	0.7906	0.4139	0.134*
H26B	0.5525	0.9408	0.4503	0.134*
H26C	0.5727	0.8178	0.5224	0.134*

	U11	U22	U33	U12	U13	U23
O1	0.0570 (7)	0.0447 (7)	0.0803 (9)	−0.0125 (6)	0.0413 (7)	−0.0052 (6)
O2	0.0555 (7)	0.0507 (7)	0.0624 (8)	−0.0152 (6)	0.0281 (6)	−0.0144 (6)
O3	0.0945 (10)	0.0629 (8)	0.1036 (11)	−0.0088 (8)	0.0734 (10)	0.0024 (8)
O4	0.0775 (9)	0.0521 (7)	0.0881 (10)	0.0029 (6)	0.0577 (8)	−0.0005 (7)
N1	0.0475 (8)	0.0464 (8)	0.0437 (8)	0.0061 (6)	0.0202 (6)	0.0065 (6)
N2	0.0579 (9)	0.0333 (7)	0.0603 (9)	−0.0026 (6)	0.0295 (7)	0.0028 (6)
C1	0.0604 (11)	0.0532 (11)	0.0598 (11)	0.0149 (9)	0.0223 (9)	0.0104 (9)
C2	0.0652 (11)	0.0552 (10)	0.0481 (10)	0.0046 (9)	0.0313 (9)	0.0099 (8)
C3	0.0543 (10)	0.0472 (9)	0.0452 (9)	−0.0055 (8)	0.0272 (8)	−0.0025 (7)
C4	0.0422 (8)	0.0358 (8)	0.0422 (8)	−0.0021 (6)	0.0225 (7)	−0.0013 (7)
C5	0.0387 (8)	0.0352 (8)	0.0410 (8)	−0.0005 (6)	0.0188 (7)	0.0005 (6)
C6	0.0364 (8)	0.0335 (8)	0.0546 (10)	0.0022 (6)	0.0207 (7)	0.0012 (7)
C7	0.0392 (8)	0.0320 (8)	0.0448 (9)	0.0037 (6)	0.0144 (7)	0.0016 (7)
C8	0.0502 (10)	0.0387 (9)	0.0521 (10)	−0.0008 (7)	0.0121 (8)	−0.0043 (8)
C9	0.0714 (12)	0.0467 (10)	0.0434 (10)	0.0045 (9)	0.0164 (9)	−0.0074 (8)
C10	0.0735 (12)	0.0481 (10)	0.0468 (10)	0.0071 (9)	0.0308 (9)	0.0015 (8)
C11	0.0523 (10)	0.0399 (8)	0.0421 (9)	0.0067 (7)	0.0231 (8)	0.0047 (7)
C12	0.0379 (8)	0.0331 (7)	0.0397 (8)	0.0048 (6)	0.0148 (7)	0.0037 (6)
C13	0.0362 (8)	0.0369 (8)	0.0411 (8)	0.0011 (6)	0.0176 (7)	0.0010 (7)
C14	0.0439 (9)	0.0511 (9)	0.0485 (9)	−0.0084 (7)	0.0219 (8)	−0.0058 (8)
C15	0.0484 (10)	0.0592 (11)	0.0664 (12)	−0.0132 (8)	0.0332 (9)	−0.0058 (9)
C16	0.0595 (11)	0.0573 (11)	0.0617 (11)	−0.0001 (9)	0.0402 (10)	0.0039 (9)
C17	0.0493 (9)	0.0376 (8)	0.0502 (9)	−0.0058 (7)	0.0290 (8)	−0.0091 (7)
C18	0.0411 (8)	0.0375 (8)	0.0454 (9)	0.0009 (6)	0.0241 (7)	−0.0023 (7)
C19	0.0502 (9)	0.0367 (8)	0.0483 (9)	0.0029 (7)	0.0273 (8)	−0.0026 (7)
C20	0.0653 (12)	0.0455 (10)	0.0572 (11)	0.0148 (9)	0.0274 (10)	0.0066 (8)
C21	0.0496 (10)	0.0622 (12)	0.0623 (12)	0.0147 (9)	0.0177 (9)	−0.0045 (10)
C22	0.0416 (10)	0.0616 (11)	0.0709 (12)	0.0012 (8)	0.0230 (9)	−0.0092 (10)
C23	0.0457 (9)	0.0454 (9)	0.0608 (11)	−0.0004 (7)	0.0277 (8)	−0.0006 (8)
C24	0.0924 (16)	0.0405 (10)	0.0951 (16)	−0.0103 (10)	0.0438 (13)	0.0119 (10)
C25	0.0649 (11)	0.0489 (10)	0.0522 (10)	−0.0087 (8)	0.0371 (9)	−0.0056 (8)
C26	0.0934 (17)	0.0816 (16)	0.127 (2)	0.0184 (13)	0.0803 (17)	0.0055 (14)

O1—C6	1.2135 (18)	C9—C10	1.369 (3)
O2—C17	1.2178 (19)	C9—H9	0.9300
O3—C25	1.198 (2)	C10—C11	1.408 (2)
O4—C25	1.328 (2)	C10—H10	0.9300
O4—C26	1.436 (2)	C11—C12	1.402 (2)
N1—C2	1.453 (2)	C11—C16	1.408 (2)
N1—C1	1.459 (2)	C12—C13	1.407 (2)
N1—C5	1.4622 (19)	C13—C14	1.367 (2)
N2—C17	1.354 (2)	C14—C15	1.410 (2)
N2—C19	1.403 (2)	C14—H14	0.9300
N2—C24	1.455 (2)	C15—C16	1.360 (3)
C1—H1A	0.9600	C15—H15	0.9300
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C18—C23	1.379 (2)
C2—C3	1.513 (2)	C18—C19	1.389 (2)
C2—H2A	0.9700	C19—C20	1.374 (2)
C2—H2B	0.9700	C20—C21	1.379 (3)
C3—C25	1.494 (2)	C20—H20	0.9300
C3—C4	1.564 (2)	C21—C22	1.376 (3)
C3—H3	0.9800	C21—H21	0.9300
C4—C18	1.514 (2)	C22—C23	1.387 (2)
C4—C17	1.539 (2)	C22—H22	0.9300
C4—C5	1.590 (2)	C23—H23	0.9300
C5—C13	1.520 (2)	C24—H24A	0.9600
C5—C6	1.572 (2)	C24—H24B	0.9600
C6—C7	1.471 (2)	C24—H24C	0.9600
C7—C8	1.371 (2)	C26—H26A	0.9600
C7—C12	1.400 (2)	C26—H26B	0.9600
C8—C9	1.403 (2)	C26—H26C	0.9600
C8—H8	0.9300
C25—O4—C26	117.20 (15)	C12—C11—C16	116.49 (15)
C2—N1—C1	115.01 (14)	C10—C11—C16	127.37 (16)
C2—N1—C5	107.70 (12)	C7—C12—C11	122.73 (14)
C1—N1—C5	115.53 (13)	C7—C12—C13	113.46 (13)
C17—N2—C19	111.21 (13)	C11—C12—C13	123.65 (14)
C17—N2—C24	123.77 (15)	C14—C13—C12	118.01 (14)
C19—N2—C24	124.40 (15)	C14—C13—C5	132.55 (14)
N1—C1—H1A	109.5	C12—C13—C5	109.14 (12)
N1—C1—H1B	109.5	C13—C14—C15	119.08 (15)
H1A—C1—H1B	109.5	C13—C14—H14	120.5
N1—C1—H1C	109.5	C15—C14—H14	120.5
H1A—C1—H1C	109.5	C16—C15—C14	122.79 (16)
H1B—C1—H1C	109.5	C16—C15—H15	118.6
N1—C2—C3	102.59 (13)	C14—C15—H15	118.6
N1—C2—H2A	111.2	C15—C16—C11	119.94 (15)
C3—C2—H2A	111.2	C15—C16—H16	120.0
N1—C2—H2B	111.2	C11—C16—H16	120.0
C3—C2—H2B	111.2	O2—C17—N2	125.31 (15)
H2A—C2—H2B	109.2	O2—C17—C4	126.49 (15)
C25—C3—C2	114.31 (14)	N2—C17—C4	108.19 (13)
C25—C3—C4	114.51 (14)	C23—C18—C19	118.95 (15)
C2—C3—C4	105.51 (13)	C23—C18—C4	132.22 (14)
C25—C3—H3	107.4	C19—C18—C4	108.63 (13)
C2—C3—H3	107.4	C20—C19—C18	122.52 (16)
C4—C3—H3	107.4	C20—C19—N2	127.77 (16)
C18—C4—C17	101.45 (12)	C18—C19—N2	109.61 (14)
C18—C4—C3	117.85 (12)	C19—C20—C21	117.63 (17)
C17—C4—C3	108.74 (12)	C19—C20—H20	121.2
C18—C4—C5	115.01 (12)	C21—C20—H20	121.2
C17—C4—C5	110.31 (12)	C22—C21—C20	121.07 (17)
C3—C4—C5	103.43 (12)	C22—C21—H21	119.5
N1—C5—C13	111.32 (12)	C20—C21—H21	119.5
N1—C5—C6	112.02 (12)	C21—C22—C23	120.68 (17)
C13—C5—C6	101.67 (12)	C21—C22—H22	119.7
N1—C5—C4	102.87 (11)	C23—C22—H22	119.7
C13—C5—C4	117.40 (12)	C18—C23—C22	119.14 (16)
C6—C5—C4	111.90 (11)	C18—C23—H23	120.4
O1—C6—C7	126.75 (15)	C22—C23—H23	120.4
O1—C6—C5	124.52 (14)	N2—C24—H24A	109.5
C7—C6—C5	108.34 (12)	N2—C24—H24B	109.5
C8—C7—C12	119.87 (15)	H24A—C24—H24B	109.5
C8—C7—C6	132.72 (15)	N2—C24—H24C	109.5
C12—C7—C6	107.13 (13)	H24A—C24—H24C	109.5
C7—C8—C9	118.06 (16)	H24B—C24—H24C	109.5
C7—C8—H8	121.0	O3—C25—O4	123.53 (17)
C9—C8—H8	121.0	O3—C25—C3	125.34 (17)
C10—C9—C8	122.29 (16)	O4—C25—C3	111.12 (14)
C10—C9—H9	118.9	O4—C26—H26A	109.5
C8—C9—H9	118.9	O4—C26—H26B	109.5
C9—C10—C11	120.90 (16)	H26A—C26—H26B	109.5
C9—C10—H10	119.5	O4—C26—H26C	109.5
C11—C10—H10	119.5	H26A—C26—H26C	109.5
C12—C11—C10	116.09 (15)	H26B—C26—H26C	109.5
C1—N1—C2—C3	−174.54 (14)	C7—C12—C13—C5	−0.36 (17)
C5—N1—C2—C3	−44.14 (16)	C11—C12—C13—C5	−175.79 (13)
N1—C2—C3—C25	158.48 (14)	N1—C5—C13—C14	−50.7 (2)
N1—C2—C3—C4	31.78 (17)	C6—C5—C13—C14	−170.18 (17)
C25—C3—C4—C18	−8.3 (2)	C4—C5—C13—C14	67.4 (2)
C2—C3—C4—C18	118.29 (15)	N1—C5—C13—C12	122.71 (13)
C25—C3—C4—C17	106.29 (16)	C6—C5—C13—C12	3.27 (15)
C2—C3—C4—C17	−127.12 (14)	C4—C5—C13—C12	−119.15 (14)
C25—C3—C4—C5	−136.46 (14)	C12—C13—C14—C15	2.0 (2)
C2—C3—C4—C5	−9.87 (16)	C5—C13—C14—C15	174.98 (16)
C2—N1—C5—C13	163.81 (13)	C13—C14—C15—C16	−1.2 (3)
C1—N1—C5—C13	−66.09 (17)	C14—C15—C16—C11	−0.5 (3)
C2—N1—C5—C6	−83.11 (15)	C12—C11—C16—C15	1.3 (2)
C1—N1—C5—C6	47.00 (18)	C10—C11—C16—C15	−176.25 (17)
C2—N1—C5—C4	37.23 (15)	C19—N2—C17—O2	−169.50 (15)
C1—N1—C5—C4	167.34 (13)	C24—N2—C17—O2	1.8 (3)
C18—C4—C5—N1	−145.28 (12)	C19—N2—C17—C4	9.62 (17)
C17—C4—C5—N1	100.76 (14)	C24—N2—C17—C4	−179.04 (16)
C3—C4—C5—N1	−15.38 (14)	C18—C4—C17—O2	169.98 (15)
C18—C4—C5—C13	92.14 (15)	C3—C4—C17—O2	45.1 (2)
C17—C4—C5—C13	−21.82 (18)	C5—C4—C17—O2	−67.68 (19)
C3—C4—C5—C13	−137.96 (13)	C18—C4—C17—N2	−9.13 (15)
C18—C4—C5—C6	−24.86 (17)	C3—C4—C17—N2	−134.01 (13)
C17—C4—C5—C6	−138.82 (13)	C5—C4—C17—N2	113.21 (14)
C3—C4—C5—C6	105.04 (14)	C17—C4—C18—C23	−169.12 (16)
N1—C5—C6—O1	49.29 (19)	C3—C4—C18—C23	−50.6 (2)
C13—C5—C6—O1	168.23 (14)	C5—C4—C18—C23	71.8 (2)
C4—C5—C6—O1	−65.65 (19)	C17—C4—C18—C19	5.61 (15)
N1—C5—C6—C7	−123.94 (13)	C3—C4—C18—C19	124.14 (14)
C13—C5—C6—C7	−5.00 (15)	C5—C4—C18—C19	−113.43 (14)
C4—C5—C6—C7	121.13 (13)	C23—C18—C19—C20	−1.4 (2)
O1—C6—C7—C8	5.6 (3)	C4—C18—C19—C20	−176.94 (15)
C5—C6—C7—C8	178.65 (16)	C23—C18—C19—N2	175.13 (14)
O1—C6—C7—C12	−168.02 (15)	C4—C18—C19—N2	−0.41 (17)
C5—C6—C7—C12	5.01 (16)	C17—N2—C19—C20	170.31 (16)
C12—C7—C8—C9	0.0 (2)	C24—N2—C19—C20	−1.0 (3)
C6—C7—C8—C9	−172.97 (16)	C17—N2—C19—C18	−5.99 (18)
C7—C8—C9—C10	1.7 (3)	C24—N2—C19—C18	−177.26 (16)
C8—C9—C10—C11	−1.4 (3)	C18—C19—C20—C21	1.0 (2)
C9—C10—C11—C12	−0.6 (2)	N2—C19—C20—C21	−174.81 (16)
C9—C10—C11—C16	176.92 (17)	C19—C20—C21—C22	0.1 (3)
C8—C7—C12—C11	−2.1 (2)	C20—C21—C22—C23	−0.8 (3)
C6—C7—C12—C11	172.48 (13)	C19—C18—C23—C22	0.6 (2)
C8—C7—C12—C13	−177.61 (13)	C4—C18—C23—C22	174.91 (16)
C6—C7—C12—C13	−3.00 (17)	C21—C22—C23—C18	0.4 (3)
C10—C11—C12—C7	2.4 (2)	C26—O4—C25—O3	−3.1 (3)
C16—C11—C12—C7	−175.42 (14)	C26—O4—C25—C3	176.22 (17)
C10—C11—C12—C13	177.41 (14)	C2—C3—C25—O3	−7.5 (3)
C16—C11—C12—C13	−0.4 (2)	C4—C3—C25—O3	114.4 (2)
C7—C12—C13—C14	174.18 (14)	C2—C3—C25—O4	173.17 (15)
C11—C12—C13—C14	−1.3 (2)	C4—C3—C25—O4	−64.93 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.60	3.268 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.60	3.268 (2)	130

Symmetry code: (i) .