supplementary materials
5-Bromo-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-one
The title compound, C13H9BrO, has been synthesized by the intramolecular Friedel-Crafts reaction of 1-(1-bromo-4-naphthyl)-3-chloropropan-1-one. There are two approximately planar [maximum deviations of 0.8 (2) and 0.4 (2) Å in the two molecules] molecules in the asymmetric unit. The dihedral angle between their mean planes is 19.72 (8)°. Weak intermolecular C-H
O hydrogen bonding is present in the crystal structure.
All reagents and solvents were used as obtained commercially without further
purification. The title compound was synthesized by adding
1-(1-bromonaphthalen-4-yl)-3-chloropropan-1-one (1.4 mL) to concentrated
H2SO4 (11 ml) at room temperature. The resulting mixture was stirred at
383 K for 3 h, after cooling to room temperature, the mixture was
poured into water-ice slowly. The aqueous layer was extracted with cyclohexane
(3 × 60 mL). The organic layers were combined and washed with
saturated NaHCO3 solution (120 mL), saturated brine (3 × 60 ml), and
dried over MgSO4, and concentrated under reduced pressure to provide the
title compound. The compound was dissolved in CH2Cl2 and kept in darkness
for several days, yellow block-shaped single crystals were obtained.
H atoms were generated geometrically with C—H 0.93 or 0.97 Å and were
allowed to ride on their parent atoms in the riding model approximations, with
Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2009).
5-Bromo-2,3-dihydro-1
H-cyclopenta[
a]naphthalen-1-one
top
Crystal data top
| 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 | |
Data collection top
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 top
| 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 |
Crystal data top
| C13H9BrO | γ = 87.154 (7)° |
| Mr = 261.10 | V = 1022.3 (5) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 7.369 (2) Å | Mo Kα radiation |
| b = 9.986 (3) Å | µ = 3.99 mm−1 |
| c = 14.177 (5) Å | T = 298 K |
| α = 87.763 (6)° | 0.09 × 0.08 × 0.06 mm |
| β = 78.991 (6)° | |
Data collection top
Oxford Gemini S Ultra
diffractometer | 3524 independent reflections |
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008) | 2663 reflections with I > 2σ(I) |
| Tmin = 0.716, Tmax = 0.796 | Rint = 0.023 |
| 5159 measured reflections | θmax = 25.0° |
Refinement top
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.119 | Δρmax = 0.52 e Å−3 |
| S = 0.97 | Δρmin = −0.40 e Å−3 |
| 3524 reflections | Absolute structure: ? |
| 271 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | 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) | |
Atomic displacement parameters (Å2) top| | 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) |
Geometric parameters (Å, °) top
| 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) |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15A···O1i | 0.97 | 2.54 | 3.495 (5) | 167 |
| Symmetry codes: (i) x, y−1, z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15A···O1i | 0.97 | 2.54 | 3.495 (5) | 167 |
| Symmetry codes: (i) x, y−1, z+1. |
Amick, A. W. & Scott, L. T. (2007). J. Org. Chem. 72, 3412–3418.
Boorum, M. M., Vasil'ev, Y. V., Drewello, T. & Scott, L. T. (2001). Science, 294, 828–831.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Scott, L. T., Bratcher, M. S. & Hagen, S. (1996). J. Am. Chem. Soc. 118, 8743–8744.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sil, D., Sharon, A., Maulik, P. R. & Ram, V. J. (2004). Tetrahedron Lett. 45, 6619–6621.
Westrip, S. (2009). publCIF. In preparation.
![[Figure 1]](./xu2577fig1thm.gif)
The title compound is the medial compound for the synthesis of its trimmer molecule. In the acid conditions, the trimmer molecule can be obtained by the Aldol cyclotrimerization of 5-bromo-2,3-dihydrocyclopenta[a]naphthalen-1-one. These kinds of the trimmers are the potential intermediate in the synthesis of fullerenes (Boorum et al., 2001; Scott et al., 1996). So this method was widely used in the organic synthesis of fullerenes and bowl-shaped compounds (Amick & Scott, 2007).
The molecular structure is depicted in Fig. 1. Bond lengths and angles are in good agreement with previous reported for similar compounds (Sil et al., 2004). The molecule assumes a co-planar structure, except methylene H atoms. The asymmetric unit of the crystal structure contains two independent molecules, the two molecular planes make a dihedral angle of 19.72 (8)° with respect to each other. Weak intermolecular C—H···O hydrogen bonding (Table 1) is present in the crystal structure(Fig. 2).