3-(1-Adamant-yl)-6-methyl-3-(3-methyl-benz-yl)isochroman-1-one.

In the title compound, C(28)H(32)O(2), the oxanone ring adopts distorted half-boat conformation with the following Cremer and Pople puckering parameters: Q = 0.619 (2) Å, θ = 0.75 (19) and ϕ = 172 (13)°. The dihedral angle betwen two benzene rings is 21.32 (7)°. The adamantane unit consists of three fused cyclo-hexane rings in classical chair conformations, with absolute values of C-C-C-C torsion angles in the range 57.5 (2)-60.9 (2)°. Weak inter-actions of the type C-H⋯O link mol-ecules of each enanti-omer into chains parallel to the b axis and lying about inversion centers. The crystal packing is also stabilized by inter-molecular π-π stacking inter-actions [centroid-centroid distance of 3.8566 (11) Å].

Related literature

For related structure and the preparation method, see: Vícha et al. (2006 ▶). For the biological activity of related compounds, see: Buntin et al. (2008 ▶); Bianchi et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H32O2

M = 400.54

Monoclinic,

a = 25.691 (5) Å

b = 6.8474 (14) Å

c = 24.465 (5) Å

β = 95.62 (3)°

V = 4283.1 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.50 × 0.40 × 0.40 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: multi-scan (; Oxford Diffraction, 2006 ▶) T min = 0.928, T max = 0.976

24394 measured reflections

3768 independent reflections

2791 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.151

S = 1.09

3768 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015888/pv2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015888/pv2152Isup2.hkl

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

C28H32O2	F(000) = 1728
Mr = 400.54	Dx = 1.242 Mg m−3
Monoclinic, C2/c	Melting point: 448(1) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.691 (5) Å	Cell parameters from 3768 reflections
b = 6.8474 (14) Å	θ = 3.1–25.0°
c = 24.465 (5) Å	µ = 0.08 mm−1
β = 95.62 (3)°	T = 120 K
V = 4283.1 (15) Å3	Block, colourless
Z = 8	0.50 × 0.40 × 0.40 mm

Kuma KM-4-CCD diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	2791 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 0.06 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −26→30
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −8→8
Tmin = 0.928, Tmax = 0.976	l = −29→29
24394 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0809P)2 + 3.6011P] where P = (Fo2 + 2Fc2)/3
3768 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.30 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	0.12111 (5)	0.58024 (19)	0.42951 (5)	0.0274 (3)
O2	0.10665 (6)	0.8319 (2)	0.48112 (6)	0.0416 (4)
C1	0.12676 (7)	0.3506 (3)	0.35689 (7)	0.0249 (4)
C2	0.07450 (8)	0.4117 (4)	0.32486 (8)	0.0357 (5)
H2A	0.0461	0.3273	0.3359	0.043*
H2B	0.0663	0.5482	0.3342	0.043*
C3	0.07703 (8)	0.3948 (4)	0.26254 (8)	0.0415 (6)
H3A	0.0426	0.4347	0.2431	0.050*
C4	0.08847 (10)	0.1837 (4)	0.24825 (9)	0.0508 (7)
H4A	0.0899	0.1707	0.2081	0.061*
H4B	0.0603	0.0978	0.2592	0.061*
C5	0.14076 (10)	0.1229 (3)	0.27842 (9)	0.0424 (6)
H5A	0.1484	−0.0153	0.2687	0.051*
C6	0.18356 (9)	0.2548 (4)	0.26050 (9)	0.0406 (6)
H6A	0.1852	0.2425	0.2204	0.049*
H6B	0.2178	0.2149	0.2792	0.049*
C7	0.17210 (8)	0.4660 (3)	0.27493 (8)	0.0337 (5)
H7A	0.2005	0.5523	0.2634	0.040*
C8	0.16969 (8)	0.4845 (3)	0.33713 (8)	0.0299 (5)
H8A	0.1623	0.6219	0.3464	0.036*
H8B	0.2040	0.4486	0.3565	0.036*
C9	0.11992 (9)	0.5274 (4)	0.24478 (8)	0.0395 (5)
H9A	0.1123	0.6649	0.2536	0.047*
H9B	0.1215	0.5168	0.2046	0.047*
C10	0.13864 (9)	0.1386 (3)	0.34079 (8)	0.0351 (5)
H10A	0.1726	0.0972	0.3600	0.042*
H10B	0.1111	0.0506	0.3523	0.042*
C11	0.12507 (7)	0.3690 (3)	0.42072 (7)	0.0245 (4)
C12	0.07750 (8)	0.2678 (3)	0.44128 (7)	0.0255 (4)
H12A	0.0463	0.2945	0.4152	0.031*
H12B	0.0834	0.1249	0.4419	0.031*
C13	0.06683 (7)	0.3338 (3)	0.49754 (7)	0.0240 (4)
C14	0.04511 (7)	0.2122 (3)	0.53459 (7)	0.0265 (4)
H14A	0.0368	0.0812	0.5243	0.032*
C15	0.03512 (7)	0.2773 (3)	0.58642 (7)	0.0286 (5)
C16	0.04774 (8)	0.4696 (3)	0.60077 (8)	0.0302 (5)
H16A	0.0414	0.5165	0.6361	0.036*
C17	0.06931 (8)	0.5930 (3)	0.56449 (8)	0.0294 (5)
H17A	0.0778	0.7238	0.5749	0.035*
C18	0.07859 (7)	0.5254 (3)	0.51267 (7)	0.0247 (4)
C19	0.10280 (8)	0.6571 (3)	0.47482 (8)	0.0276 (5)
C20	0.01153 (9)	0.1436 (3)	0.62600 (8)	0.0383 (5)
H20A	0.0237	0.0098	0.6209	0.057*
H20B	−0.0267	0.1480	0.6193	0.057*
H20C	0.0222	0.1858	0.6637	0.057*
C21	0.17657 (8)	0.2921 (3)	0.45125 (8)	0.0326 (5)
H21A	0.1763	0.1479	0.4485	0.039*
H21B	0.2059	0.3397	0.4314	0.039*
C22	0.18831 (8)	0.3455 (3)	0.51107 (8)	0.0298 (5)
C23	0.17789 (8)	0.2147 (3)	0.55169 (8)	0.0313 (5)
H23A	0.1640	0.0900	0.5415	0.038*
C24	0.18731 (8)	0.2613 (3)	0.60726 (8)	0.0353 (5)
C25	0.20832 (8)	0.4433 (4)	0.62145 (8)	0.0389 (5)
H25A	0.2145	0.4785	0.6591	0.047*
C26	0.22031 (8)	0.5736 (4)	0.58156 (9)	0.0392 (5)
H26A	0.2354	0.6965	0.5918	0.047*
C27	0.21027 (8)	0.5250 (3)	0.52660 (8)	0.0353 (5)
H27A	0.2185	0.6153	0.4992	0.042*
C28	0.17439 (10)	0.1205 (4)	0.64983 (10)	0.0515 (7)
H28A	0.1786	−0.0129	0.6365	0.077*
H28B	0.1381	0.1403	0.6578	0.077*
H28C	0.1979	0.1410	0.6834	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0340 (8)	0.0251 (7)	0.0238 (7)	0.0011 (6)	0.0060 (6)	−0.0008 (5)
O2	0.0616 (11)	0.0269 (9)	0.0376 (9)	0.0005 (7)	0.0125 (7)	−0.0030 (6)
C1	0.0240 (10)	0.0316 (11)	0.0193 (9)	0.0020 (8)	0.0032 (7)	−0.0006 (8)
C2	0.0255 (11)	0.0581 (15)	0.0236 (10)	0.0035 (10)	0.0027 (8)	0.0044 (9)
C3	0.0251 (12)	0.0774 (17)	0.0216 (10)	−0.0017 (11)	0.0003 (8)	0.0049 (10)
C4	0.0537 (16)	0.0751 (18)	0.0243 (11)	−0.0294 (14)	0.0074 (10)	−0.0101 (11)
C5	0.0597 (16)	0.0416 (13)	0.0274 (11)	−0.0029 (11)	0.0122 (10)	−0.0102 (9)
C6	0.0399 (13)	0.0588 (15)	0.0246 (10)	0.0040 (11)	0.0101 (9)	−0.0027 (10)
C7	0.0276 (11)	0.0465 (13)	0.0278 (10)	−0.0056 (9)	0.0062 (8)	0.0019 (9)
C8	0.0280 (11)	0.0364 (12)	0.0252 (10)	−0.0040 (9)	0.0020 (8)	0.0001 (8)
C9	0.0425 (14)	0.0534 (14)	0.0225 (10)	0.0030 (11)	0.0033 (9)	0.0047 (9)
C10	0.0432 (13)	0.0369 (12)	0.0259 (10)	−0.0020 (10)	0.0077 (9)	−0.0039 (9)
C11	0.0276 (11)	0.0243 (10)	0.0219 (10)	0.0040 (8)	0.0039 (8)	−0.0024 (7)
C12	0.0315 (11)	0.0231 (10)	0.0222 (9)	0.0002 (8)	0.0039 (8)	−0.0001 (7)
C13	0.0203 (10)	0.0281 (10)	0.0231 (9)	0.0063 (8)	0.0004 (7)	−0.0012 (8)
C14	0.0252 (11)	0.0285 (10)	0.0259 (10)	0.0014 (8)	0.0027 (8)	−0.0001 (8)
C15	0.0227 (11)	0.0398 (12)	0.0234 (10)	0.0039 (8)	0.0035 (8)	0.0025 (8)
C16	0.0266 (11)	0.0427 (12)	0.0218 (9)	0.0082 (9)	0.0053 (8)	−0.0026 (8)
C17	0.0312 (11)	0.0291 (11)	0.0280 (10)	0.0050 (8)	0.0038 (8)	−0.0047 (8)
C18	0.0227 (10)	0.0273 (10)	0.0240 (9)	0.0068 (8)	0.0024 (8)	0.0012 (8)
C19	0.0326 (12)	0.0259 (11)	0.0243 (10)	0.0052 (8)	0.0025 (8)	−0.0028 (8)
C20	0.0385 (13)	0.0475 (14)	0.0303 (11)	0.0021 (10)	0.0101 (9)	0.0037 (9)
C21	0.0308 (12)	0.0465 (13)	0.0202 (10)	0.0108 (9)	0.0009 (8)	−0.0025 (9)
C22	0.0234 (11)	0.0434 (12)	0.0224 (10)	0.0099 (9)	0.0018 (8)	0.0003 (9)
C23	0.0235 (11)	0.0400 (12)	0.0302 (11)	0.0094 (9)	0.0013 (8)	−0.0025 (9)
C24	0.0272 (11)	0.0541 (14)	0.0254 (10)	0.0145 (10)	0.0064 (8)	0.0055 (9)
C25	0.0307 (12)	0.0591 (15)	0.0262 (11)	0.0079 (10)	−0.0007 (9)	−0.0088 (10)
C26	0.0296 (12)	0.0514 (14)	0.0357 (12)	−0.0026 (10)	−0.0019 (9)	−0.0097 (10)
C27	0.0279 (12)	0.0465 (13)	0.0313 (11)	−0.0013 (9)	0.0012 (9)	0.0000 (9)
C28	0.0539 (16)	0.0593 (16)	0.0423 (14)	0.0055 (13)	0.0102 (11)	0.0120 (12)

O1—C19	1.353 (2)	C12—H12A	0.9900
O1—C11	1.467 (2)	C12—H12B	0.9900
O2—C19	1.209 (2)	C13—C14	1.388 (3)
C1—C10	1.542 (3)	C13—C18	1.388 (3)
C1—C2	1.544 (3)	C14—C15	1.391 (3)
C1—C8	1.548 (3)	C14—H14A	0.9500
C1—C11	1.572 (2)	C15—C16	1.393 (3)
C2—C3	1.537 (3)	C15—C20	1.503 (3)
C2—H2A	0.9900	C16—C17	1.381 (3)
C2—H2B	0.9900	C16—H16A	0.9500
C3—C4	1.523 (4)	C17—C18	1.392 (3)
C3—C9	1.524 (3)	C17—H17A	0.9500
C3—H3A	1.0000	C18—C19	1.474 (3)
C4—C5	1.526 (4)	C20—H20A	0.9800
C4—H4A	0.9900	C20—H20B	0.9800
C4—H4B	0.9900	C20—H20C	0.9800
C5—C6	1.520 (3)	C21—C22	1.510 (3)
C5—C10	1.536 (3)	C21—H21A	0.9900
C5—H5A	1.0000	C21—H21B	0.9900
C6—C7	1.525 (3)	C22—C23	1.383 (3)
C6—H6A	0.9900	C22—C27	1.390 (3)
C6—H6B	0.9900	C23—C24	1.394 (3)
C7—C9	1.524 (3)	C23—H23A	0.9500
C7—C8	1.534 (3)	C24—C25	1.389 (3)
C7—H7A	1.0000	C24—C28	1.481 (3)
C8—H8A	0.9900	C25—C26	1.379 (3)
C8—H8B	0.9900	C25—H25A	0.9500
C9—H9A	0.9900	C26—C27	1.385 (3)
C9—H9B	0.9900	C26—H26A	0.9500
C10—H10A	0.9900	C27—H27A	0.9500
C10—H10B	0.9900	C28—H28A	0.9800
C11—C12	1.532 (3)	C28—H28B	0.9800
C11—C21	1.547 (3)	C28—H28C	0.9800
C12—C13	1.500 (2)
C19—O1—C11	122.58 (14)	C12—C11—C1	112.97 (15)
C10—C1—C2	108.02 (16)	C21—C11—C1	110.29 (15)
C10—C1—C8	108.25 (16)	C13—C12—C11	112.85 (15)
C2—C1—C8	106.96 (16)	C13—C12—H12A	109.0
C10—C1—C11	110.79 (15)	C11—C12—H12A	109.0
C2—C1—C11	112.03 (15)	C13—C12—H12B	109.0
C8—C1—C11	110.63 (15)	C11—C12—H12B	109.0
C3—C2—C1	111.34 (17)	H12A—C12—H12B	107.8
C3—C2—H2A	109.4	C14—C13—C18	118.94 (17)
C1—C2—H2A	109.4	C14—C13—C12	122.69 (17)
C3—C2—H2B	109.4	C18—C13—C12	118.37 (17)
C1—C2—H2B	109.4	C13—C14—C15	121.66 (18)
H2A—C2—H2B	108.0	C13—C14—H14A	119.2
C4—C3—C9	109.82 (19)	C15—C14—H14A	119.2
C4—C3—C2	109.08 (19)	C14—C15—C16	118.26 (18)
C9—C3—C2	109.89 (18)	C14—C15—C20	120.94 (19)
C4—C3—H3A	109.3	C16—C15—C20	120.80 (18)
C9—C3—H3A	109.3	C17—C16—C15	120.99 (18)
C2—C3—H3A	109.3	C17—C16—H16A	119.5
C3—C4—C5	109.19 (18)	C15—C16—H16A	119.5
C3—C4—H4A	109.8	C16—C17—C18	119.81 (18)
C5—C4—H4A	109.8	C16—C17—H17A	120.1
C3—C4—H4B	109.8	C18—C17—H17A	120.1
C5—C4—H4B	109.8	C13—C18—C17	120.34 (18)
H4A—C4—H4B	108.3	C13—C18—C19	120.35 (16)
C6—C5—C4	109.0 (2)	C17—C18—C19	119.28 (17)
C6—C5—C10	109.99 (18)	O2—C19—O1	117.32 (18)
C4—C5—C10	110.25 (19)	O2—C19—C18	124.05 (18)
C6—C5—H5A	109.2	O1—C19—C18	118.61 (16)
C4—C5—H5A	109.2	C15—C20—H20A	109.5
C10—C5—H5A	109.2	C15—C20—H20B	109.5
C5—C6—C7	109.59 (18)	H20A—C20—H20B	109.5
C5—C6—H6A	109.8	C15—C20—H20C	109.5
C7—C6—H6A	109.8	H20A—C20—H20C	109.5
C5—C6—H6B	109.8	H20B—C20—H20C	109.5
C7—C6—H6B	109.8	C22—C21—C11	117.76 (16)
H6A—C6—H6B	108.2	C22—C21—H21A	107.9
C9—C7—C6	109.28 (18)	C11—C21—H21A	107.9
C9—C7—C8	109.76 (17)	C22—C21—H21B	107.9
C6—C7—C8	109.59 (17)	C11—C21—H21B	107.9
C9—C7—H7A	109.4	H21A—C21—H21B	107.2
C6—C7—H7A	109.4	C23—C22—C27	118.57 (18)
C8—C7—H7A	109.4	C23—C22—C21	120.35 (19)
C7—C8—C1	111.10 (16)	C27—C22—C21	121.08 (18)
C7—C8—H8A	109.4	C22—C23—C24	121.7 (2)
C1—C8—H8A	109.4	C22—C23—H23A	119.2
C7—C8—H8B	109.4	C24—C23—H23A	119.2
C1—C8—H8B	109.4	C25—C24—C23	118.4 (2)
H8A—C8—H8B	108.0	C25—C24—C28	121.1 (2)
C3—C9—C7	108.92 (18)	C23—C24—C28	120.5 (2)
C3—C9—H9A	109.9	C26—C25—C24	120.80 (19)
C7—C9—H9A	109.9	C26—C25—H25A	119.6
C3—C9—H9B	109.9	C24—C25—H25A	119.6
C7—C9—H9B	109.9	C25—C26—C27	119.9 (2)
H9A—C9—H9B	108.3	C25—C26—H26A	120.1
C5—C10—C1	110.29 (17)	C27—C26—H26A	120.1
C5—C10—H10A	109.6	C26—C27—C22	120.7 (2)
C1—C10—H10A	109.6	C26—C27—H27A	119.7
C5—C10—H10B	109.6	C22—C27—H27A	119.7
C1—C10—H10B	109.6	C24—C28—H28A	109.5
H10A—C10—H10B	108.1	C24—C28—H28B	109.5
O1—C11—C12	109.21 (15)	H28A—C28—H28B	109.5
O1—C11—C21	109.47 (15)	C24—C28—H28C	109.5
C12—C11—C21	111.07 (16)	H28A—C28—H28C	109.5
O1—C11—C1	103.53 (14)	H28B—C28—H28C	109.5
C10—C1—C2—C3	−58.3 (2)	O1—C11—C12—C13	−48.1 (2)
C8—C1—C2—C3	58.0 (2)	C21—C11—C12—C13	72.7 (2)
C11—C1—C2—C3	179.39 (18)	C1—C11—C12—C13	−162.74 (15)
C1—C2—C3—C4	60.2 (2)	C11—C12—C13—C14	−148.46 (17)
C1—C2—C3—C9	−60.2 (3)	C11—C12—C13—C18	32.4 (2)
C9—C3—C4—C5	60.5 (2)	C18—C13—C14—C15	−0.3 (3)
C2—C3—C4—C5	−60.0 (2)	C12—C13—C14—C15	−179.42 (17)
C3—C4—C5—C6	−60.2 (2)	C13—C14—C15—C16	−0.3 (3)
C3—C4—C5—C10	60.6 (2)	C13—C14—C15—C20	179.94 (18)
C4—C5—C6—C7	60.6 (2)	C14—C15—C16—C17	0.4 (3)
C10—C5—C6—C7	−60.4 (2)	C20—C15—C16—C17	−179.86 (18)
C5—C6—C7—C9	−60.8 (2)	C15—C16—C17—C18	0.1 (3)
C5—C6—C7—C8	59.5 (2)	C14—C13—C18—C17	0.8 (3)
C9—C7—C8—C1	60.9 (2)	C12—C13—C18—C17	179.98 (17)
C6—C7—C8—C1	−59.1 (2)	C14—C13—C18—C19	178.59 (16)
C10—C1—C8—C7	57.8 (2)	C12—C13—C18—C19	−2.3 (3)
C2—C1—C8—C7	−58.3 (2)	C16—C17—C18—C13	−0.8 (3)
C11—C1—C8—C7	179.39 (16)	C16—C17—C18—C19	−178.54 (17)
C4—C3—C9—C7	−60.3 (2)	C11—O1—C19—O2	171.77 (17)
C2—C3—C9—C7	59.7 (2)	C11—O1—C19—C18	−9.5 (3)
C6—C7—C9—C3	60.1 (2)	C13—C18—C19—O2	167.88 (19)
C8—C7—C9—C3	−60.1 (2)	C17—C18—C19—O2	−14.3 (3)
C6—C5—C10—C1	60.3 (2)	C13—C18—C19—O1	−10.8 (3)
C4—C5—C10—C1	−60.0 (2)	C17—C18—C19—O1	166.98 (17)
C2—C1—C10—C5	57.5 (2)	O1—C11—C21—C22	50.9 (2)
C8—C1—C10—C5	−57.9 (2)	C12—C11—C21—C22	−69.7 (2)
C11—C1—C10—C5	−179.40 (17)	C1—C11—C21—C22	164.23 (17)
C19—O1—C11—C12	38.5 (2)	C11—C21—C22—C23	98.7 (2)
C19—O1—C11—C21	−83.3 (2)	C11—C21—C22—C27	−82.1 (2)
C19—O1—C11—C1	159.11 (15)	C27—C22—C23—C24	2.1 (3)
C10—C1—C11—O1	172.14 (15)	C21—C22—C23—C24	−178.67 (18)
C2—C1—C11—O1	−67.16 (19)	C22—C23—C24—C25	−0.8 (3)
C8—C1—C11—O1	52.08 (19)	C22—C23—C24—C28	178.27 (19)
C10—C1—C11—C12	−69.8 (2)	C23—C24—C25—C26	−1.0 (3)
C2—C1—C11—C12	50.9 (2)	C28—C24—C25—C26	179.9 (2)
C8—C1—C11—C12	170.09 (15)	C24—C25—C26—C27	1.5 (3)
C10—C1—C11—C21	55.1 (2)	C25—C26—C27—C22	−0.2 (3)
C2—C1—C11—C21	175.81 (17)	C23—C22—C27—C26	−1.5 (3)
C8—C1—C11—C21	−64.9 (2)	C21—C22—C27—C26	179.21 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O2i	0.95	2.65	3.548 (3)	157
C12—H12B···O2i	0.99	2.28	3.206 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23A⋯O2i	0.95	2.65	3.548 (3)	157
C12—H12B⋯O2i	0.99	2.28	3.206 (2)	156

Symmetry code: (i) .