16-Oxa-penta-cyclo-[6.6.5.0(1,18).0(2,7).0(9,14)]nona-deca-2,4,6,9,11,13,18-heptaen-15-one.

In the title compound, C18H12O2, the benzene rings are inclined to one another by 66.79 (7)°. The five-membered ring is almost planar with a maximum deviation of 0.014 (1) Å. In the crystal, the mol-ecules are linked by pairs of weak C-H⋯O interactions into centrosymmetric dimers. These dimers are linked by C-H⋯π interactions, forming a three-dimensional structure.

Related literature

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010 ▶); Cox et al. (2013 ▶). For the synthesis of related compounds, see: Ciganek (1980 ▶); De Luca et al. (2001 ▶). For a related structure, see: Mathew et al. (2013 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H12O2

M = 260.28

Monoclinic,

a = 9.351 (1) Å

b = 13.8153 (16) Å

c = 10.1514 (9) Å

β = 105.295 (4)°

V = 1265.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.966, T max = 0.974

9570 measured reflections

3123 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.03

3123 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814000026/yk2102sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000026/yk2102Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000026/yk2102Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H12O2	F(000) = 544
Mr = 260.28	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2538 reflections
a = 9.351 (1) Å	θ = 2.7–27.2°
b = 13.8153 (16) Å	µ = 0.09 mm−1
c = 10.1514 (9) Å	T = 296 K
β = 105.295 (4)°	Block, colourless
V = 1265.0 (2) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	3123 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.33 pixels mm-1	θmax = 28.3°, θmin = 2.7°
ω and φ scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −18→18
Tmin = 0.966, Tmax = 0.974	l = −9→13
9570 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.0884P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3123 reflections	Δρmax = 0.22 e Å−3
182 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

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	0.80024 (14)	−0.01503 (9)	0.22190 (12)	0.0570 (4)
O2	0.81229 (15)	−0.05665 (8)	0.43556 (13)	0.0590 (4)
C1	0.35542 (16)	0.23405 (12)	0.28342 (15)	0.0410 (4)
H1	0.3188	0.2869	0.3209	0.049*
C2	0.27224 (16)	0.19194 (12)	0.16350 (15)	0.0454 (4)
H2	0.1799	0.2175	0.1198	0.054*
C3	0.32484 (18)	0.11291 (12)	0.10856 (15)	0.0440 (4)
H3	0.2663	0.0840	0.0300	0.053*
C4	0.46477 (17)	0.07589 (11)	0.16959 (13)	0.0368 (3)
H4	0.5010	0.0230	0.1318	0.044*
C5	0.54912 (15)	0.11890 (10)	0.28707 (13)	0.0294 (3)
C6	0.49305 (15)	0.19640 (10)	0.34614 (13)	0.0323 (3)
C7	0.59990 (16)	0.23295 (11)	0.47731 (13)	0.0372 (4)
H7	0.5584	0.2858	0.5201	0.045*
C8	0.73588 (15)	0.26293 (10)	0.43345 (13)	0.0329 (3)
C9	0.79945 (18)	0.35413 (11)	0.44610 (15)	0.0426 (4)
H9	0.7627	0.4033	0.4905	0.051*
C10	0.91836 (18)	0.37120 (12)	0.39195 (16)	0.0472 (4)
H10	0.9615	0.4323	0.4001	0.057*
C11	0.97316 (17)	0.29906 (12)	0.32652 (16)	0.0462 (4)
H11	1.0519	0.3120	0.2893	0.055*
C12	0.91213 (15)	0.20649 (11)	0.31525 (14)	0.0373 (3)
H12	0.9503	0.1573	0.2720	0.045*
C13	0.79444 (14)	0.18928 (10)	0.36931 (12)	0.0297 (3)
C14	0.70748 (15)	0.09493 (10)	0.36761 (13)	0.0298 (3)
C15	0.77607 (17)	0.00483 (11)	0.32910 (16)	0.0408 (4)
C16	0.7720 (2)	−0.01959 (13)	0.55478 (17)	0.0566 (5)
H16A	0.8592	−0.0126	0.6311	0.068*
H16B	0.7028	−0.0629	0.5813	0.068*
C17	0.70234 (16)	0.07596 (12)	0.51340 (14)	0.0375 (3)
C18	0.64493 (17)	0.14591 (12)	0.57090 (14)	0.0419 (4)
H18	0.6331	0.1426	0.6589	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0749 (9)	0.0426 (7)	0.0586 (7)	0.0140 (6)	0.0266 (6)	−0.0097 (6)
O2	0.0767 (9)	0.0353 (7)	0.0645 (8)	0.0168 (6)	0.0177 (6)	0.0126 (6)
C1	0.0341 (8)	0.0432 (9)	0.0454 (8)	0.0049 (6)	0.0097 (6)	−0.0012 (7)
C2	0.0322 (8)	0.0528 (10)	0.0457 (8)	−0.0005 (7)	0.0005 (7)	0.0072 (7)
C3	0.0429 (8)	0.0487 (10)	0.0339 (7)	−0.0133 (7)	−0.0015 (6)	0.0007 (7)
C4	0.0452 (8)	0.0319 (7)	0.0332 (7)	−0.0058 (6)	0.0099 (6)	−0.0028 (6)
C5	0.0327 (7)	0.0288 (7)	0.0268 (6)	−0.0021 (5)	0.0079 (5)	0.0025 (5)
C6	0.0311 (7)	0.0355 (8)	0.0304 (6)	−0.0006 (5)	0.0085 (5)	0.0000 (6)
C7	0.0383 (8)	0.0412 (8)	0.0311 (7)	0.0048 (6)	0.0076 (6)	−0.0096 (6)
C8	0.0330 (7)	0.0337 (7)	0.0276 (6)	0.0023 (6)	0.0003 (5)	−0.0045 (5)
C9	0.0451 (9)	0.0339 (8)	0.0396 (8)	0.0026 (6)	−0.0049 (7)	−0.0080 (6)
C10	0.0407 (9)	0.0386 (9)	0.0532 (9)	−0.0103 (7)	−0.0035 (7)	0.0001 (7)
C11	0.0296 (7)	0.0513 (10)	0.0542 (9)	−0.0062 (6)	0.0051 (7)	0.0080 (8)
C12	0.0292 (7)	0.0400 (8)	0.0417 (7)	0.0033 (6)	0.0073 (6)	0.0026 (6)
C13	0.0295 (7)	0.0289 (7)	0.0279 (6)	0.0029 (5)	0.0026 (5)	0.0007 (5)
C14	0.0337 (7)	0.0271 (7)	0.0286 (6)	0.0017 (5)	0.0080 (5)	0.0002 (5)
C15	0.0437 (8)	0.0306 (8)	0.0477 (8)	0.0037 (6)	0.0111 (7)	−0.0007 (7)
C16	0.0646 (11)	0.0535 (11)	0.0507 (9)	0.0097 (9)	0.0136 (9)	0.0200 (8)
C17	0.0371 (8)	0.0429 (8)	0.0307 (7)	0.0001 (6)	0.0056 (6)	0.0074 (6)
C18	0.0426 (8)	0.0582 (10)	0.0251 (6)	−0.0012 (7)	0.0092 (6)	0.0013 (6)

O1—C15	1.2001 (19)	C8—C9	1.385 (2)
O2—C15	1.3457 (19)	C8—C13	1.3955 (19)
O2—C16	1.452 (2)	C9—C10	1.384 (2)
C1—C6	1.3783 (19)	C9—H9	0.9300
C1—C2	1.388 (2)	C10—C11	1.370 (2)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.375 (2)	C11—C12	1.393 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (2)	C12—C13	1.374 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.3788 (19)	C13—C14	1.5339 (19)
C4—H4	0.9300	C14—C15	1.499 (2)
C5—C6	1.395 (2)	C14—C17	1.5163 (18)
C5—C14	1.5272 (18)	C16—C17	1.483 (2)
C6—C7	1.5246 (18)	C16—H16A	0.9700
C7—C8	1.512 (2)	C16—H16B	0.9700
C7—C18	1.521 (2)	C17—C18	1.315 (2)
C7—H7	0.9800	C18—H18	0.9300
C15—O2—C16	112.40 (12)	C11—C10—H10	119.6
C6—C1—C2	119.08 (15)	C9—C10—H10	119.6
C6—C1—H1	120.5	C10—C11—C12	120.68 (15)
C2—C1—H1	120.5	C10—C11—H11	119.7
C3—C2—C1	120.74 (14)	C12—C11—H11	119.7
C3—C2—H2	119.6	C13—C12—C11	118.69 (14)
C1—C2—H2	119.6	C13—C12—H12	120.7
C2—C3—C4	120.47 (13)	C11—C12—H12	120.7
C2—C3—H3	119.8	C12—C13—C8	120.96 (13)
C4—C3—H3	119.8	C12—C13—C14	128.37 (12)
C5—C4—C3	118.93 (14)	C8—C13—C14	110.66 (12)
C5—C4—H4	120.5	C15—C14—C17	103.71 (12)
C3—C4—H4	120.5	C15—C14—C5	117.50 (11)
C4—C5—C6	120.55 (13)	C17—C14—C5	106.50 (11)
C4—C5—C14	128.48 (13)	C15—C14—C13	116.53 (12)
C6—C5—C14	110.95 (11)	C17—C14—C13	106.81 (11)
C1—C6—C5	120.13 (13)	C5—C14—C13	104.96 (10)
C1—C6—C7	126.55 (14)	O1—C15—O2	121.07 (14)
C5—C6—C7	113.29 (11)	O1—C15—C14	128.49 (14)
C8—C7—C18	106.55 (12)	O2—C15—C14	110.44 (13)
C8—C7—C6	104.00 (11)	O2—C16—C17	105.60 (12)
C18—C7—C6	107.06 (12)	O2—C16—H16A	110.6
C8—C7—H7	112.9	C17—C16—H16A	110.6
C18—C7—H7	112.9	O2—C16—H16B	110.6
C6—C7—H7	112.9	C17—C16—H16B	110.6
C9—C8—C13	119.68 (14)	H16A—C16—H16B	108.8
C9—C8—C7	126.58 (14)	C18—C17—C16	136.81 (14)
C13—C8—C7	113.68 (12)	C18—C17—C14	115.35 (13)
C10—C9—C8	119.23 (14)	C16—C17—C14	107.80 (13)
C10—C9—H9	120.4	C17—C18—C7	112.45 (12)
C8—C9—H9	120.4	C17—C18—H18	123.8
C11—C10—C9	120.73 (15)	C7—C18—H18	123.8
C6—C1—C2—C3	0.9 (2)	C4—C5—C14—C17	−125.40 (15)
C1—C2—C3—C4	−2.3 (2)	C6—C5—C14—C17	56.01 (15)
C2—C3—C4—C5	0.8 (2)	C4—C5—C14—C13	121.57 (15)
C3—C4—C5—C6	2.0 (2)	C6—C5—C14—C13	−57.03 (14)
C3—C4—C5—C14	−176.46 (13)	C12—C13—C14—C15	13.99 (19)
C2—C1—C6—C5	1.9 (2)	C8—C13—C14—C15	−167.52 (11)
C2—C1—C6—C7	179.78 (14)	C12—C13—C14—C17	129.29 (14)
C4—C5—C6—C1	−3.4 (2)	C8—C13—C14—C17	−52.22 (14)
C14—C5—C6—C1	175.29 (12)	C12—C13—C14—C5	−117.89 (14)
C4—C5—C6—C7	178.45 (12)	C8—C13—C14—C5	60.60 (13)
C14—C5—C6—C7	−2.83 (17)	C16—O2—C15—O1	−179.23 (15)
C1—C6—C7—C8	−118.49 (16)	C16—O2—C15—C14	1.30 (19)
C5—C6—C7—C8	59.48 (15)	C17—C14—C15—O1	178.30 (16)
C1—C6—C7—C18	128.95 (16)	C5—C14—C15—O1	61.1 (2)
C5—C6—C7—C18	−53.07 (16)	C13—C14—C15—O1	−64.7 (2)
C18—C7—C8—C9	−125.80 (15)	C17—C14—C15—O2	−2.28 (16)
C6—C7—C8—C9	121.28 (15)	C5—C14—C15—O2	−119.45 (14)
C18—C7—C8—C13	57.06 (14)	C13—C14—C15—O2	114.75 (14)
C6—C7—C8—C13	−55.86 (15)	C15—O2—C16—C17	0.30 (19)
C13—C8—C9—C10	1.4 (2)	O2—C16—C17—C18	−178.90 (18)
C7—C8—C9—C10	−175.55 (13)	O2—C16—C17—C14	−1.73 (17)
C8—C9—C10—C11	0.0 (2)	C15—C14—C17—C18	−179.75 (13)
C9—C10—C11—C12	−1.2 (2)	C5—C14—C17—C18	−55.14 (16)
C10—C11—C12—C13	0.9 (2)	C13—C14—C17—C18	56.61 (16)
C11—C12—C13—C8	0.5 (2)	C15—C14—C17—C16	2.39 (16)
C11—C12—C13—C14	178.84 (12)	C5—C14—C17—C16	127.00 (13)
C9—C8—C13—C12	−1.7 (2)	C13—C14—C17—C16	−121.24 (13)
C7—C8—C13—C12	175.68 (11)	C16—C17—C18—C7	175.33 (18)
C9—C8—C13—C14	179.70 (11)	C14—C17—C18—C7	−1.69 (19)
C7—C8—C13—C14	−2.94 (15)	C8—C7—C18—C17	−54.71 (16)
C4—C5—C14—C15	−9.8 (2)	C6—C7—C18—C17	56.09 (17)
C6—C5—C14—C15	171.65 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1i	0.98	2.92	3.7835 (16)	148
C16—H16B···Cg1ii	0.97	2.76	3.650 (2)	153
C18—H18···Cg2i	0.93	2.84	3.3942 (16)	120
C3—H3···O1iii	0.93	2.64	3.519 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.98	2.92	3.7835 (16)	148
C16—H16B⋯Cg1ii	0.97	2.76	3.650 (2)	153
C18—H18⋯Cg2i	0.93	2.84	3.3942 (16)	120
C3—H3⋯O1iii	0.93	2.64	3.519 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) .