5-Bromo-2,3-dihydro-1H-cyclo-penta-[a]naphthalen-1-one.

The title compound, C(13)H(9)BrO, has been synthesized by the intra-molecular Friedel-Crafts reaction of 1-(1-bromo-4-naphth-yl)-3-chloro-propan-1-one. There are two approximately planar [maximum deviations of 0.8 (2) and 0.4 (2) Å in the two mol-ecules] molecules in the asymmetric unit. The dihedral angle between their mean planes is 19.72 (8)°. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

The trimer of the title compound is a potential inter­mediate in the synthesis of fullerenes, see: Boorum et al. (2001 ▶); Scott et al. (1996 ▶). The Aldol cyclo­trimerization of the title compound is widely used in the synthesis of fullerenes and bowl-shaped compounds, see: Amick & Scott (2007 ▶). For a related structure, see: Sil et al. (2004 ▶).

Experimental

Crystal data

C13H9BrO

M = 261.10

Triclinic,

a = 7.369 (2) Å

b = 9.986 (3) Å

c = 14.177 (5) Å

α = 87.763 (6)°

β = 78.991 (6)°

γ = 87.154 (7)°

V = 1022.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.99 mm−1

T = 298 K

0.09 × 0.08 × 0.06 mm

Data collection

Oxford Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.716, T max = 0.796

5159 measured reflections

3524 independent reflections

2663 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 0.97

3524 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031547/xu2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031547/xu2577Isup2.hkl

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

C13H9BrO	Z = 4
Mr = 261.10	F(000) = 520
Triclinic, P1	Dx = 1.696 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.369 (2) Å	Cell parameters from 2244 reflections
b = 9.986 (3) Å	θ = 5.0–51.6°
c = 14.177 (5) Å	µ = 3.99 mm−1
α = 87.763 (6)°	T = 298 K
β = 78.991 (6)°	Block, yellow
γ = 87.154 (7)°	0.09 × 0.08 × 0.06 mm
V = 1022.3 (5) Å3

Oxford Gemini S Ultra diffractometer	3524 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 16.1903 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −11→7
Tmin = 0.716, Tmax = 0.796	l = −16→16
5159 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0728P)2] where P = (Fo2 + 2Fc2)/3
3524 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.40 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
Br1	0.65084 (6)	0.55540 (4)	0.27810 (3)	0.06465 (19)
Br2	0.91872 (7)	0.04342 (5)	0.24015 (3)	0.07118 (19)
C1	0.8141 (5)	0.4593 (4)	−0.1539 (3)	0.0496 (9)
C2	0.8305 (6)	0.3098 (4)	−0.1488 (3)	0.0595 (11)
H2A	0.9522	0.2786	−0.1815	0.071*
H2B	0.7384	0.2722	−0.1794	0.071*
C3	0.8005 (6)	0.2664 (4)	−0.0430 (3)	0.0574 (10)
H3A	0.6953	0.2096	−0.0262	0.069*
H3B	0.9093	0.2181	−0.0279	0.069*
C4	0.7646 (5)	0.3963 (3)	0.0089 (3)	0.0428 (8)
C5	0.7302 (5)	0.4116 (4)	0.1088 (3)	0.0507 (9)
H5A	0.7291	0.3373	0.1505	0.061*
C6	0.6988 (5)	0.5365 (4)	0.1428 (3)	0.0454 (9)
C7	0.7025 (5)	0.6556 (3)	0.0827 (2)	0.0406 (8)
C8	0.6704 (5)	0.7859 (3)	0.1171 (3)	0.0480 (9)
H8A	0.6451	0.7985	0.1830	0.058*
C9	0.6756 (5)	0.8937 (4)	0.0558 (3)	0.0540 (10)
H9A	0.6544	0.9794	0.0801	0.065*
C10	0.7121 (5)	0.8774 (4)	−0.0427 (3)	0.0527 (9)
H10A	0.7146	0.9523	−0.0840	0.063*
C11	0.7444 (5)	0.7531 (3)	−0.0796 (3)	0.0477 (9)
H11A	0.7701	0.7435	−0.1459	0.057*
C12	0.7392 (5)	0.6376 (3)	−0.0175 (2)	0.0397 (8)
C13	0.7711 (5)	0.5055 (4)	−0.0526 (3)	0.0416 (8)
C14	0.6249 (5)	−0.0807 (4)	0.6648 (3)	0.0528 (10)
C15	0.5904 (6)	−0.2280 (4)	0.6573 (3)	0.0656 (12)
H15A	0.6664	−0.2829	0.6938	0.079*
H15B	0.4615	−0.2452	0.6825	0.079*
C16	0.6392 (5)	−0.2604 (4)	0.5528 (3)	0.0551 (10)
H16A	0.5316	−0.2878	0.5296	0.066*
H16B	0.7347	−0.3316	0.5420	0.066*
C17	0.7091 (4)	−0.1300 (3)	0.5032 (3)	0.0435 (9)
C18	0.7752 (5)	−0.1078 (4)	0.4049 (3)	0.0498 (9)
H18A	0.7815	−0.1767	0.3620	0.060*
C19	0.8295 (5)	0.0155 (4)	0.3739 (3)	0.0462 (9)
C20	0.8236 (4)	0.1243 (3)	0.4364 (3)	0.0416 (8)
C21	0.8801 (5)	0.2544 (4)	0.4031 (3)	0.0491 (9)
H21A	0.9247	0.2718	0.3381	0.059*
C22	0.8680 (5)	0.3541 (4)	0.4681 (3)	0.0569 (11)
H22A	0.9033	0.4396	0.4459	0.068*
C23	0.8054 (5)	0.3321 (4)	0.5651 (3)	0.0543 (10)
H23A	0.8014	0.4011	0.6077	0.065*
C24	0.7489 (5)	0.2069 (4)	0.5980 (3)	0.0542 (10)
H24A	0.7043	0.1923	0.6633	0.065*
C25	0.7569 (5)	0.1006 (3)	0.5352 (3)	0.0429 (9)
C26	0.7001 (5)	−0.0297 (3)	0.5667 (3)	0.0414 (8)
O1	0.8324 (5)	0.5286 (3)	−0.2259 (2)	0.0722 (9)
O2	0.5922 (4)	−0.0199 (3)	0.7378 (2)	0.0781 (9)

	U11	U22	U33	U12	U13	U23
Br1	0.0910 (4)	0.0609 (3)	0.0390 (3)	−0.0119 (2)	−0.0041 (2)	0.00645 (18)
Br2	0.0765 (3)	0.0813 (4)	0.0490 (3)	−0.0153 (2)	0.0092 (2)	−0.0078 (2)
C1	0.045 (2)	0.051 (2)	0.054 (2)	0.0024 (17)	−0.0130 (19)	−0.0079 (19)
C2	0.065 (3)	0.057 (3)	0.056 (3)	−0.003 (2)	−0.008 (2)	−0.015 (2)
C3	0.058 (3)	0.041 (2)	0.074 (3)	−0.0061 (18)	−0.011 (2)	−0.0051 (19)
C4	0.0401 (19)	0.037 (2)	0.051 (2)	−0.0083 (15)	−0.0050 (16)	−0.0017 (16)
C5	0.059 (2)	0.042 (2)	0.050 (2)	−0.0074 (18)	−0.0108 (19)	0.0109 (17)
C6	0.050 (2)	0.047 (2)	0.039 (2)	−0.0091 (17)	−0.0047 (17)	0.0022 (16)
C7	0.0395 (19)	0.041 (2)	0.041 (2)	−0.0082 (15)	−0.0069 (16)	0.0048 (15)
C8	0.053 (2)	0.045 (2)	0.045 (2)	−0.0002 (17)	−0.0088 (18)	−0.0033 (17)
C9	0.064 (3)	0.035 (2)	0.063 (3)	−0.0005 (18)	−0.013 (2)	−0.0006 (17)
C10	0.062 (3)	0.043 (2)	0.051 (2)	−0.0005 (18)	−0.0076 (19)	0.0106 (17)
C11	0.058 (2)	0.045 (2)	0.039 (2)	−0.0037 (18)	−0.0066 (18)	0.0081 (16)
C12	0.0379 (19)	0.0370 (19)	0.044 (2)	−0.0035 (15)	−0.0072 (16)	0.0030 (15)
C13	0.039 (2)	0.042 (2)	0.044 (2)	−0.0062 (15)	−0.0080 (16)	−0.0005 (15)
C14	0.045 (2)	0.061 (3)	0.054 (3)	−0.0040 (19)	−0.0141 (19)	0.012 (2)
C15	0.059 (3)	0.061 (3)	0.080 (3)	−0.013 (2)	−0.024 (2)	0.031 (2)
C16	0.046 (2)	0.038 (2)	0.083 (3)	−0.0077 (17)	−0.017 (2)	0.0108 (19)
C17	0.0309 (18)	0.042 (2)	0.059 (2)	−0.0021 (15)	−0.0142 (17)	0.0055 (17)
C18	0.045 (2)	0.041 (2)	0.064 (3)	−0.0022 (17)	−0.0090 (19)	−0.0090 (18)
C19	0.040 (2)	0.055 (2)	0.040 (2)	−0.0015 (17)	−0.0010 (16)	0.0007 (16)
C20	0.0318 (18)	0.041 (2)	0.051 (2)	−0.0002 (15)	−0.0073 (16)	0.0004 (16)
C21	0.043 (2)	0.048 (2)	0.058 (2)	−0.0121 (17)	−0.0121 (18)	0.0083 (18)
C22	0.059 (3)	0.034 (2)	0.081 (3)	−0.0123 (18)	−0.020 (2)	0.004 (2)
C23	0.053 (2)	0.045 (2)	0.067 (3)	−0.0079 (18)	−0.015 (2)	−0.016 (2)
C24	0.056 (2)	0.057 (3)	0.052 (2)	−0.0019 (19)	−0.013 (2)	−0.0053 (19)
C25	0.0360 (19)	0.042 (2)	0.052 (2)	0.0007 (15)	−0.0123 (17)	−0.0037 (16)
C26	0.040 (2)	0.042 (2)	0.044 (2)	−0.0029 (16)	−0.0117 (16)	0.0053 (15)
O1	0.098 (2)	0.079 (2)	0.0383 (17)	0.0139 (17)	−0.0135 (16)	−0.0042 (15)
O2	0.092 (2)	0.089 (2)	0.052 (2)	−0.0133 (18)	−0.0097 (17)	0.0082 (17)

Br1—C6	1.898 (4)	C12—C13	1.421 (5)
Br2—C19	1.899 (4)	C14—O2	1.198 (5)
C1—O1	1.200 (5)	C14—C26	1.476 (5)
C1—C2	1.492 (5)	C14—C15	1.517 (6)
C1—C13	1.496 (5)	C15—C16	1.501 (6)
C2—C3	1.522 (6)	C15—H15A	0.9700
C2—H2A	0.9700	C15—H15B	0.9700
C2—H2B	0.9700	C16—C17	1.521 (5)
C3—C4	1.504 (5)	C16—H16A	0.9700
C3—H3A	0.9700	C16—H16B	0.9700
C3—H3B	0.9700	C17—C26	1.364 (5)
C4—C13	1.366 (5)	C17—C18	1.398 (5)
C4—C5	1.403 (5)	C18—C19	1.345 (5)
C5—C6	1.349 (5)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.423 (5)
C6—C7	1.434 (5)	C20—C25	1.408 (5)
C7—C8	1.400 (5)	C20—C21	1.420 (5)
C7—C12	1.412 (5)	C21—C22	1.371 (5)
C8—C9	1.354 (5)	C21—H21A	0.9300
C8—H8A	0.9300	C22—C23	1.376 (6)
C9—C10	1.386 (5)	C22—H22A	0.9300
C9—H9A	0.9300	C23—C24	1.373 (6)
C10—C11	1.358 (5)	C23—H23A	0.9300
C10—H10A	0.9300	C24—C25	1.404 (5)
C11—C12	1.421 (5)	C24—H24A	0.9300
C11—H11A	0.9300	C25—C26	1.416 (5)
O1—C1—C2	126.2 (4)	O2—C14—C26	128.1 (4)
O1—C1—C13	126.9 (4)	O2—C14—C15	124.9 (4)
C2—C1—C13	106.9 (3)	C26—C14—C15	107.0 (3)
C1—C2—C3	107.6 (3)	C16—C15—C14	107.2 (3)
C1—C2—H2A	110.2	C16—C15—H15A	110.3
C3—C2—H2A	110.2	C14—C15—H15A	110.3
C1—C2—H2B	110.2	C16—C15—H15B	110.3
C3—C2—H2B	110.2	C14—C15—H15B	110.3
H2A—C2—H2B	108.5	H15A—C15—H15B	108.5
C4—C3—C2	103.8 (3)	C15—C16—C17	104.2 (3)
C4—C3—H3A	111.0	C15—C16—H16A	110.9
C2—C3—H3A	111.0	C17—C16—H16A	110.9
C4—C3—H3B	111.0	C15—C16—H16B	110.9
C2—C3—H3B	111.0	C17—C16—H16B	110.9
H3A—C3—H3B	109.0	H16A—C16—H16B	108.9
C13—C4—C5	120.9 (3)	C26—C17—C18	121.2 (3)
C13—C4—C3	112.5 (3)	C26—C17—C16	111.9 (4)
C5—C4—C3	126.6 (3)	C18—C17—C16	127.0 (3)
C6—C5—C4	118.4 (3)	C19—C18—C17	118.5 (3)
C6—C5—H5A	120.8	C19—C18—H18A	120.7
C4—C5—H5A	120.8	C17—C18—H18A	120.7
C5—C6—C7	123.8 (3)	C18—C19—C20	123.1 (4)
C5—C6—Br1	117.9 (3)	C18—C19—Br2	117.8 (3)
C7—C6—Br1	118.3 (3)	C20—C19—Br2	119.1 (3)
C8—C7—C12	119.0 (3)	C25—C20—C21	119.4 (3)
C8—C7—C6	124.4 (3)	C25—C20—C19	117.9 (3)
C12—C7—C6	116.7 (3)	C21—C20—C19	122.8 (4)
C9—C8—C7	121.0 (4)	C22—C21—C20	119.0 (4)
C9—C8—H8A	119.5	C22—C21—H21A	120.5
C7—C8—H8A	119.5	C20—C21—H21A	120.5
C8—C9—C10	120.6 (4)	C21—C22—C23	122.3 (4)
C8—C9—H9A	119.7	C21—C22—H22A	118.8
C10—C9—H9A	119.7	C23—C22—H22A	118.8
C11—C10—C9	120.6 (4)	C24—C23—C22	119.1 (4)
C11—C10—H10A	119.7	C24—C23—H23A	120.4
C9—C10—H10A	119.7	C22—C23—H23A	120.4
C10—C11—C12	120.4 (3)	C23—C24—C25	121.4 (4)
C10—C11—H11A	119.8	C23—C24—H24A	119.3
C12—C11—H11A	119.8	C25—C24—H24A	119.3
C7—C12—C13	119.1 (3)	C24—C25—C20	118.7 (4)
C7—C12—C11	118.4 (3)	C24—C25—C26	122.9 (4)
C13—C12—C11	122.5 (3)	C20—C25—C26	118.3 (3)
C4—C13—C12	121.1 (3)	C17—C26—C25	121.0 (3)
C4—C13—C1	109.1 (3)	C17—C26—C14	109.7 (3)
C12—C13—C1	129.7 (3)	C25—C26—C14	129.3 (3)
O1—C1—C2—C3	178.9 (4)	O1—C1—C2—C3	178.9 (4)
C13—C1—C2—C3	−1.1 (4)	C13—C1—C2—C3	−1.1 (4)
C1—C2—C3—C4	0.8 (4)	C1—C2—C3—C4	0.8 (4)
C2—C3—C4—C13	−0.2 (4)	C2—C3—C4—C13	−0.2 (4)
C2—C3—C4—C5	−179.3 (4)	C2—C3—C4—C5	−179.3 (4)
C13—C4—C5—C6	1.7 (5)	C13—C4—C5—C6	1.7 (5)
C3—C4—C5—C6	−179.3 (3)	C3—C4—C5—C6	−179.3 (3)
C4—C5—C6—C7	−1.4 (6)	C4—C5—C6—C7	−1.4 (6)
C4—C5—C6—Br1	179.6 (3)	C4—C5—C6—Br1	179.6 (3)
C5—C6—C7—C8	−179.9 (3)	C5—C6—C7—C8	−179.9 (3)
Br1—C6—C7—C8	−0.9 (5)	Br1—C6—C7—C8	−0.9 (5)
C5—C6—C7—C12	0.8 (5)	C5—C6—C7—C12	0.8 (5)
Br1—C6—C7—C12	179.8 (2)	Br1—C6—C7—C12	179.8 (2)
C12—C7—C8—C9	−0.5 (5)	C12—C7—C8—C9	−0.5 (5)
C6—C7—C8—C9	−179.8 (4)	C6—C7—C8—C9	−179.8 (4)
C7—C8—C9—C10	0.3 (6)	C7—C8—C9—C10	0.3 (6)
C8—C9—C10—C11	−0.4 (6)	C8—C9—C10—C11	−0.4 (6)
C9—C10—C11—C12	0.7 (6)	C9—C10—C11—C12	0.7 (6)
C8—C7—C12—C13	−179.7 (3)	C8—C7—C12—C13	−179.7 (3)
C6—C7—C12—C13	−0.5 (5)	C6—C7—C12—C13	−0.5 (5)
C8—C7—C12—C11	0.8 (5)	C8—C7—C12—C11	0.8 (5)
C6—C7—C12—C11	−179.9 (3)	C6—C7—C12—C11	−179.9 (3)
C10—C11—C12—C7	−0.9 (5)	C10—C11—C12—C7	−0.9 (5)
C10—C11—C12—C13	179.7 (3)	C10—C11—C12—C13	179.7 (3)
C5—C4—C13—C12	−1.4 (5)	C5—C4—C13—C12	−1.4 (5)
C3—C4—C13—C12	179.4 (3)	C3—C4—C13—C12	179.4 (3)
C5—C4—C13—C1	178.7 (3)	C5—C4—C13—C1	178.7 (3)
C3—C4—C13—C1	−0.5 (4)	C3—C4—C13—C1	−0.5 (4)
C7—C12—C13—C4	0.8 (5)	C7—C12—C13—C4	0.8 (5)
C11—C12—C13—C4	−179.8 (3)	C11—C12—C13—C4	−179.8 (3)
C7—C12—C13—C1	−179.3 (3)	C7—C12—C13—C1	−179.3 (3)
C11—C12—C13—C1	0.0 (6)	C11—C12—C13—C1	0.0 (6)
O1—C1—C13—C4	−179.0 (4)	O1—C1—C13—C4	−179.0 (4)
C2—C1—C13—C4	1.0 (4)	C2—C1—C13—C4	1.0 (4)
O1—C1—C13—C12	1.1 (7)	O1—C1—C13—C12	1.1 (7)
C2—C1—C13—C12	−178.9 (3)	C2—C1—C13—C12	−178.9 (3)
O2—C14—C15—C16	176.4 (4)	O2—C14—C15—C16	176.4 (4)
C26—C14—C15—C16	−2.3 (4)	C26—C14—C15—C16	−2.3 (4)
C14—C15—C16—C17	2.3 (4)	C14—C15—C16—C17	2.3 (4)
C15—C16—C17—C26	−1.6 (4)	C15—C16—C17—C26	−1.6 (4)
C15—C16—C17—C18	178.8 (3)	C15—C16—C17—C18	178.8 (3)
C26—C17—C18—C19	−0.3 (5)	C26—C17—C18—C19	−0.3 (5)
C16—C17—C18—C19	179.3 (3)	C16—C17—C18—C19	179.3 (3)
C17—C18—C19—C20	0.3 (5)	C17—C18—C19—C20	0.3 (5)
C17—C18—C19—Br2	−180.0 (2)	C17—C18—C19—Br2	−180.0 (2)
C18—C19—C20—C25	−0.2 (5)	C18—C19—C20—C25	−0.2 (5)
Br2—C19—C20—C25	−180.0 (2)	Br2—C19—C20—C25	−180.0 (2)
C18—C19—C20—C21	−179.6 (3)	C18—C19—C20—C21	−179.6 (3)
Br2—C19—C20—C21	0.6 (4)	Br2—C19—C20—C21	0.6 (4)
C25—C20—C21—C22	−0.1 (5)	C25—C20—C21—C22	−0.1 (5)
C19—C20—C21—C22	179.3 (3)	C19—C20—C21—C22	179.3 (3)
C20—C21—C22—C23	1.0 (5)	C20—C21—C22—C23	1.0 (5)
C21—C22—C23—C24	−1.5 (6)	C21—C22—C23—C24	−1.5 (6)
C22—C23—C24—C25	1.2 (6)	C22—C23—C24—C25	1.2 (6)
C23—C24—C25—C20	−0.4 (5)	C23—C24—C25—C20	−0.4 (5)
C23—C24—C25—C26	179.9 (3)	C23—C24—C25—C26	179.9 (3)
C21—C20—C25—C24	−0.2 (5)	C21—C20—C25—C24	−0.2 (5)
C19—C20—C25—C24	−179.6 (3)	C19—C20—C25—C24	−179.6 (3)
C21—C20—C25—C26	179.5 (3)	C21—C20—C25—C26	179.5 (3)
C19—C20—C25—C26	0.1 (5)	C19—C20—C25—C26	0.1 (5)
C18—C17—C26—C25	0.2 (5)	C18—C17—C26—C25	0.2 (5)
C16—C17—C26—C25	−179.4 (3)	C16—C17—C26—C25	−179.4 (3)
C18—C17—C26—C14	179.8 (3)	C18—C17—C26—C14	179.8 (3)
C16—C17—C26—C14	0.2 (4)	C16—C17—C26—C14	0.2 (4)
C24—C25—C26—C17	179.6 (3)	C24—C25—C26—C17	179.6 (3)
C20—C25—C26—C17	−0.1 (5)	C20—C25—C26—C17	−0.1 (5)
C24—C25—C26—C14	0.0 (6)	C24—C25—C26—C14	0.0 (6)
C20—C25—C26—C14	−179.7 (3)	C20—C25—C26—C14	−179.7 (3)
O2—C14—C26—C17	−177.3 (4)	O2—C14—C26—C17	−177.3 (4)
C15—C14—C26—C17	1.3 (4)	C15—C14—C26—C17	1.3 (4)
O2—C14—C26—C25	2.2 (6)	O2—C14—C26—C25	2.2 (6)
C15—C14—C26—C25	−179.1 (3)	C15—C14—C26—C25	−179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1i	0.97	2.54	3.495 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1i	0.97	2.54	3.495 (5)	167

Symmetry code: (i) .