Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012892/ci6048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012892/ci6048Isup2.hkl |
CCDC reference: 172201
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.066
- wR factor = 0.165
- Data-to-parameter ratio = 16.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
To a solution of 2-bromo-6-hydroxy-5-methoxybenz[a]anthracene in methanol was added an equimolar amount of phenyliodonium acetate. The mixture was stirred for 3 h at room temperature. After stirring, the solvent was removed in vacuo, and the residue was isolated by column chromatography. The residue afforded a brown–red solid and was recrystallized from a mixture of ethyl acetate and petroleum ether (25/75).
After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on their attached atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C20H13BrO5 | F(000) = 416 |
Mr = 413.21 | Dx = 1.670 Mg m−3 |
Triclinic, P1 | Melting point: 478 K |
a = 7.7414 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3084 (1) Å | Cell parameters from 3602 reflections |
c = 10.9583 (2) Å | θ = 2.0–28.3° |
α = 74.415 (1)° | µ = 2.53 mm−1 |
β = 78.835 (1)° | T = 293 K |
γ = 81.192 (1)° | Slab, brown-red |
V = 821.65 (2) Å3 | 0.36 × 0.26 × 0.10 mm |
Z = 2 |
Siemens SMART CCD diffractometer | 3910 independent reflections |
Radiation source: fine-focus sealed tube | 2584 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
ω scans | h = −10→10 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→13 |
Tmin = 0.463, Tmax = 0.786 | l = −14→10 |
5992 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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0817P)2] where P = (Fo2 + 2Fc2)/3 |
3910 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −1.79 e Å−3 |
C20H13BrO5 | γ = 81.192 (1)° |
Mr = 413.21 | V = 821.65 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7414 (1) Å | Mo Kα radiation |
b = 10.3084 (1) Å | µ = 2.53 mm−1 |
c = 10.9583 (2) Å | T = 293 K |
α = 74.415 (1)° | 0.36 × 0.26 × 0.10 mm |
β = 78.835 (1)° |
Siemens SMART CCD diffractometer | 3910 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2584 reflections with I > 2σ(I) |
Tmin = 0.463, Tmax = 0.786 | Rint = 0.055 |
5992 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.97 e Å−3 |
3910 reflections | Δρmin = −1.79 e Å−3 |
237 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | 0.57346 (6) | 0.92224 (5) | −0.32252 (4) | 0.0438 (2) | |
O1 | −0.1343 (5) | 0.9058 (4) | 0.4296 (3) | 0.0588 (11) | |
O2 | −0.0609 (4) | 0.6827 (3) | 0.3091 (4) | 0.0496 (9) | |
O3 | 0.3380 (4) | 0.7206 (3) | 0.3304 (3) | 0.0339 (7) | |
O4 | 0.2715 (4) | 0.5406 (3) | 0.2601 (3) | 0.0414 (8) | |
O5 | 0.1826 (5) | 1.1749 (3) | −0.0261 (3) | 0.0566 (10) | |
C1 | 0.3510 (5) | 0.9315 (4) | −0.0835 (4) | 0.0307 (9) | |
H1A | 0.3196 | 1.0213 | −0.1240 | 0.037* | |
C2 | 0.4709 (6) | 0.8504 (4) | −0.1502 (4) | 0.0326 (9) | |
C3 | 0.5201 (6) | 0.7159 (5) | −0.0940 (5) | 0.0417 (11) | |
H3A | 0.5992 | 0.6623 | −0.1402 | 0.050* | |
C4 | 0.4490 (7) | 0.6634 (4) | 0.0322 (5) | 0.0417 (11) | |
H4A | 0.4819 | 0.5734 | 0.0711 | 0.050* | |
C4A | 0.3284 (6) | 0.7424 (4) | 0.1031 (4) | 0.0297 (9) | |
C5 | 0.2551 (6) | 0.6801 (4) | 0.2428 (4) | 0.0303 (9) | |
C6 | 0.0648 (5) | 0.7460 (4) | 0.2697 (4) | 0.0293 (9) | |
C6A | 0.0531 (5) | 0.8976 (4) | 0.2343 (4) | 0.0266 (8) | |
C7 | −0.0620 (6) | 0.9695 (4) | 0.3271 (4) | 0.0330 (10) | |
C7A | −0.0786 (5) | 1.1200 (4) | 0.2898 (4) | 0.0307 (9) | |
C8 | −0.1782 (7) | 1.1923 (5) | 0.3753 (5) | 0.0447 (12) | |
H8A | −0.2306 | 1.1470 | 0.4562 | 0.054* | |
C9 | −0.1978 (7) | 1.3321 (5) | 0.3380 (5) | 0.0516 (13) | |
H9A | −0.2652 | 1.3814 | 0.3936 | 0.062* | |
C10 | −0.1183 (7) | 1.3987 (5) | 0.2190 (5) | 0.0549 (14) | |
H10A | −0.1335 | 1.4928 | 0.1951 | 0.066* | |
C11 | −0.0158 (7) | 1.3286 (5) | 0.1338 (5) | 0.0451 (12) | |
H11A | 0.0387 | 1.3748 | 0.0540 | 0.054* | |
C11A | 0.0040 (6) | 1.1872 (4) | 0.1703 (4) | 0.0308 (9) | |
C12 | 0.1186 (6) | 1.1131 (4) | 0.0790 (4) | 0.0313 (9) | |
C12A | 0.1479 (5) | 0.9610 (4) | 0.1228 (4) | 0.0237 (8) | |
C12B | 0.2766 (5) | 0.8792 (4) | 0.0443 (4) | 0.0253 (8) | |
C13 | 0.5292 (6) | 0.6987 (5) | 0.3130 (5) | 0.0452 (12) | |
H13A | 0.5712 | 0.7343 | 0.3730 | 0.068* | |
H13B | 0.5768 | 0.7439 | 0.2271 | 0.068* | |
H13C | 0.5666 | 0.6034 | 0.3273 | 0.068* | |
C14 | 0.2312 (7) | 0.4594 (5) | 0.3894 (5) | 0.0490 (13) | |
H14A | 0.1726 | 0.3840 | 0.3890 | 0.073* | |
H14B | 0.1553 | 0.5135 | 0.4414 | 0.073* | |
H14C | 0.3390 | 0.4267 | 0.4240 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0543 (3) | 0.0447 (3) | 0.0270 (3) | −0.0122 (2) | 0.00523 (19) | −0.00406 (18) |
O1 | 0.078 (3) | 0.040 (2) | 0.038 (2) | 0.0023 (19) | 0.0183 (18) | 0.0004 (15) |
O2 | 0.0394 (19) | 0.0369 (19) | 0.065 (2) | −0.0104 (16) | −0.0005 (16) | −0.0015 (16) |
O3 | 0.0350 (16) | 0.0343 (16) | 0.0302 (16) | 0.0025 (13) | −0.0087 (13) | −0.0055 (12) |
O4 | 0.066 (2) | 0.0194 (15) | 0.0302 (17) | −0.0032 (14) | 0.0054 (15) | −0.0016 (11) |
O5 | 0.084 (3) | 0.0258 (17) | 0.042 (2) | 0.0013 (17) | 0.0177 (18) | −0.0001 (14) |
C1 | 0.037 (2) | 0.026 (2) | 0.027 (2) | −0.0027 (18) | −0.0069 (17) | −0.0024 (15) |
C2 | 0.042 (2) | 0.032 (2) | 0.022 (2) | −0.0103 (19) | 0.0008 (17) | −0.0042 (16) |
C3 | 0.047 (3) | 0.035 (3) | 0.038 (3) | 0.000 (2) | 0.005 (2) | −0.0111 (19) |
C4 | 0.060 (3) | 0.020 (2) | 0.038 (3) | 0.002 (2) | 0.001 (2) | −0.0072 (17) |
C4A | 0.037 (2) | 0.022 (2) | 0.029 (2) | −0.0037 (17) | −0.0034 (17) | −0.0045 (15) |
C5 | 0.039 (2) | 0.0185 (19) | 0.030 (2) | 0.0013 (17) | −0.0037 (18) | −0.0032 (15) |
C6 | 0.034 (2) | 0.025 (2) | 0.026 (2) | −0.0025 (18) | −0.0063 (17) | −0.0013 (15) |
C6A | 0.027 (2) | 0.0213 (19) | 0.031 (2) | 0.0026 (16) | −0.0085 (16) | −0.0057 (15) |
C7 | 0.034 (2) | 0.031 (2) | 0.029 (2) | 0.0045 (18) | −0.0025 (18) | −0.0042 (17) |
C7A | 0.031 (2) | 0.029 (2) | 0.033 (2) | 0.0051 (17) | −0.0096 (18) | −0.0105 (16) |
C8 | 0.048 (3) | 0.043 (3) | 0.039 (3) | 0.004 (2) | −0.001 (2) | −0.014 (2) |
C9 | 0.066 (3) | 0.036 (3) | 0.054 (3) | 0.006 (3) | −0.003 (3) | −0.024 (2) |
C10 | 0.073 (4) | 0.028 (3) | 0.061 (4) | 0.004 (2) | 0.002 (3) | −0.019 (2) |
C11 | 0.061 (3) | 0.024 (2) | 0.046 (3) | 0.000 (2) | −0.001 (2) | −0.0092 (19) |
C11A | 0.033 (2) | 0.026 (2) | 0.033 (2) | 0.0024 (17) | −0.0081 (17) | −0.0079 (16) |
C12 | 0.033 (2) | 0.023 (2) | 0.034 (2) | 0.0016 (17) | −0.0074 (18) | −0.0018 (16) |
C12A | 0.0253 (19) | 0.0203 (19) | 0.026 (2) | 0.0008 (15) | −0.0088 (15) | −0.0058 (14) |
C12B | 0.028 (2) | 0.0212 (19) | 0.025 (2) | 0.0003 (16) | −0.0031 (16) | −0.0060 (14) |
C13 | 0.040 (3) | 0.047 (3) | 0.043 (3) | 0.004 (2) | −0.012 (2) | −0.004 (2) |
C14 | 0.071 (3) | 0.028 (2) | 0.035 (3) | −0.005 (2) | −0.001 (2) | 0.0083 (18) |
Br1—C2 | 1.896 (4) | C7A—C11A | 1.388 (6) |
O1—C7 | 1.216 (5) | C8—C9 | 1.381 (7) |
O2—C6 | 1.200 (5) | C9—C10 | 1.374 (7) |
O3—C5 | 1.430 (5) | C10—C11 | 1.387 (7) |
O4—C5 | 1.388 (5) | C11—C11A | 1.396 (6) |
O3—C13 | 1.446 (5) | C11A—C12 | 1.494 (6) |
O4—C14 | 1.441 (5) | C12—C12A | 1.506 (5) |
O5—C12 | 1.208 (5) | C12A—C12B | 1.498 (5) |
C1—C2 | 1.386 (6) | C1—H1A | 0.9300 |
C2—C3 | 1.385 (6) | C3—H3A | 0.9300 |
C3—C4 | 1.379 (6) | C4—H4A | 0.9300 |
C4—C4A | 1.402 (6) | C8—H8A | 0.9300 |
C1—C12B | 1.400 (6) | C9—H9A | 0.9300 |
C4A—C12B | 1.416 (5) | C10—H10A | 0.9300 |
C4A—C5 | 1.525 (5) | C11—H11A | 0.9300 |
C5—C6 | 1.534 (6) | C13—H13A | 0.9600 |
C6—C6A | 1.499 (5) | C13—H13B | 0.9600 |
C6A—C12A | 1.353 (6) | C13—H13C | 0.9600 |
C6A—C7 | 1.493 (6) | C14—H14A | 0.9600 |
C7—C7A | 1.487 (6) | C14—H14B | 0.9600 |
C7A—C8 | 1.395 (6) | C14—H14C | 0.9600 |
C5—O3—C13 | 116.3 (3) | O5—C12—C11A | 120.1 (4) |
C5—O4—C14 | 117.3 (3) | O5—C12—C12A | 122.3 (4) |
C2—C1—C12B | 120.5 (4) | C11A—C12—C12A | 117.6 (4) |
C1—C2—C3 | 121.7 (4) | C6A—C12A—C12B | 119.7 (3) |
C1—C2—Br1 | 120.4 (3) | C6A—C12A—C12 | 118.8 (3) |
C3—C2—Br1 | 118.0 (3) | C12B—C12A—C12 | 121.4 (3) |
C4—C3—C2 | 118.4 (4) | C1—C12B—C4A | 118.2 (4) |
C3—C4—C4A | 121.6 (4) | C1—C12B—C12A | 123.5 (4) |
C4—C4A—C12B | 119.6 (4) | C4A—C12B—C12A | 118.3 (3) |
C4—C4A—C5 | 119.6 (4) | C2—C1—H1A | 119.7 |
C12B—C4A—C5 | 120.8 (3) | C12B—C1—H1A | 119.7 |
O3—C5—O4 | 112.9 (3) | C4—C3—H3A | 120.8 |
O4—C5—C4A | 107.8 (3) | C2—C3—H3A | 120.8 |
O3—C5—C4A | 112.4 (3) | C3—C4—H4A | 119.2 |
O4—C5—C6 | 114.9 (3) | C4A—C4—H4A | 119.2 |
O3—C5—C6 | 101.4 (3) | C9—C8—H8A | 120.5 |
C4A—C5—C6 | 107.3 (3) | C7A—C8—H8A | 120.5 |
O2—C6—C5 | 123.4 (4) | C10—C9—H9A | 119.8 |
O2—C6—C6A | 124.1 (4) | C8—C9—H9A | 119.8 |
C5—C6—C6A | 112.5 (3) | C9—C10—H10A | 119.3 |
C12A—C6A—C7 | 124.0 (4) | C11—C10—H10A | 119.3 |
C12A—C6A—C6 | 118.9 (4) | C10—C11—H11A | 120.7 |
C7—C6A—C6 | 117.1 (4) | C11A—C11—H11A | 120.7 |
O1—C7—C7A | 122.5 (4) | H13A—C13—H13B | 109.5 |
O1—C7—C6A | 120.5 (4) | O3—C13—H13A | 109.5 |
C7A—C7—C6A | 117.1 (4) | O3—C13—H13B | 109.5 |
C11A—C7A—C8 | 120.7 (4) | O3—C13—H13C | 109.5 |
C11A—C7A—C7 | 119.8 (4) | H13A—C13—H13C | 109.5 |
C8—C7A—C7 | 119.5 (4) | H13B—C13—H13C | 109.5 |
C9—C8—C7A | 119.0 (5) | O4—C14—H14A | 109.5 |
C10—C9—C8 | 120.3 (4) | O4—C14—H14B | 109.5 |
C9—C10—C11 | 121.5 (5) | H14A—C14—H14B | 109.5 |
C10—C11—C11A | 118.6 (5) | O4—C14—H14C | 109.5 |
C7A—C11A—C11 | 119.8 (4) | H14A—C14—H14C | 109.5 |
C7A—C11A—C12 | 122.1 (4) | H14B—C14—H14C | 109.5 |
C11—C11A—C12 | 118.1 (4) | ||
C12B—C1—C2—C3 | 0.6 (7) | O1—C7—C7A—C8 | 1.0 (7) |
C12B—C1—C2—Br1 | −179.2 (3) | C6A—C7—C7A—C8 | −177.2 (4) |
C1—C2—C3—C4 | −1.1 (7) | C11A—C7A—C8—C9 | 1.8 (7) |
Br1—C2—C3—C4 | 178.7 (4) | C7—C7A—C8—C9 | −177.8 (5) |
C2—C3—C4—C4A | 0.6 (8) | C7A—C8—C9—C10 | −0.9 (8) |
C3—C4—C4A—C12B | 0.5 (7) | C8—C9—C10—C11 | −0.5 (9) |
C3—C4—C4A—C5 | −179.3 (4) | C9—C10—C11—C11A | 0.9 (9) |
C14—O4—C5—O3 | 47.5 (5) | C8—C7A—C11A—C11 | −1.4 (7) |
C14—O4—C5—C4A | 172.2 (4) | C7—C7A—C11A—C11 | 178.2 (4) |
C14—O4—C5—C6 | −68.2 (5) | C8—C7A—C11A—C12 | 177.0 (4) |
C13—O3—C5—O4 | 68.6 (5) | C7—C7A—C11A—C12 | −3.3 (6) |
C13—O3—C5—C4A | −53.6 (5) | C10—C11—C11A—C7A | 0.1 (7) |
C13—O3—C5—C6 | −167.9 (3) | C10—C11—C11A—C12 | −178.4 (5) |
C4—C4A—C5—O4 | −22.5 (5) | C7A—C11A—C12—O5 | 177.1 (5) |
C12B—C4A—C5—O4 | 157.8 (4) | C11—C11A—C12—O5 | −4.4 (7) |
C4—C4A—C5—O3 | 102.6 (5) | C7A—C11A—C12—C12A | −2.2 (6) |
C12B—C4A—C5—O3 | −77.2 (5) | C11—C11A—C12—C12A | 176.3 (4) |
C4—C4A—C5—C6 | −146.8 (4) | C7—C6A—C12A—C12B | 172.4 (4) |
C12B—C4A—C5—C6 | 33.5 (5) | C6—C6A—C12A—C12B | −6.5 (6) |
O3—C5—C6—O2 | −118.4 (4) | C7—C6A—C12A—C12 | −8.8 (6) |
O4—C5—C6—O2 | 3.7 (6) | C6—C6A—C12A—C12 | 172.3 (3) |
C4A—C5—C6—O2 | 123.5 (4) | O5—C12—C12A—C6A | −171.1 (5) |
O4—C5—C6—C6A | −173.1 (3) | C11A—C12—C12A—C6A | 8.2 (6) |
O3—C5—C6—C6A | 64.8 (4) | O5—C12—C12A—C12B | 7.7 (7) |
C4A—C5—C6—C6A | −53.2 (4) | C11A—C12—C12A—C12B | −173.0 (4) |
O2—C6—C6A—C12A | −134.0 (5) | C2—C1—C12B—C4A | 0.5 (6) |
C5—C6—C6A—C12A | 42.7 (5) | C2—C1—C12B—C12A | 179.3 (4) |
O2—C6—C6A—C7 | 47.0 (6) | C4—C4A—C12B—C1 | −1.0 (6) |
C5—C6—C6A—C7 | −136.3 (4) | C5—C4A—C12B—C1 | 178.8 (4) |
C12A—C6A—C7—O1 | −175.0 (5) | C4—C4A—C12B—C12A | −179.8 (4) |
C6—C6A—C7—O1 | 3.9 (6) | C5—C4A—C12B—C12A | −0.1 (6) |
C12A—C6A—C7—C7A | 3.2 (6) | C6A—C12A—C12B—C1 | 165.6 (4) |
C6—C6A—C7—C7A | −177.9 (4) | C12—C12A—C12B—C1 | −13.3 (6) |
O1—C7—C7A—C11A | −178.7 (5) | C6A—C12A—C12B—C4A | −15.6 (6) |
C6A—C7—C7A—C11A | 3.1 (6) | C12—C12A—C12B—C4A | 165.5 (4) |
Experimental details
Crystal data | |
Chemical formula | C20H13BrO5 |
Mr | 413.21 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.7414 (1), 10.3084 (1), 10.9583 (2) |
α, β, γ (°) | 74.415 (1), 78.835 (1), 81.192 (1) |
V (Å3) | 821.65 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.53 |
Crystal size (mm) | 0.36 × 0.26 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.463, 0.786 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5992, 3910, 2584 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.165, 0.94 |
No. of reflections | 3910 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −1.79 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Br1—C2 | 1.896 (4) | C4—C4A | 1.402 (6) |
O1—C7 | 1.216 (5) | C1—C12B | 1.400 (6) |
O2—C6 | 1.200 (5) | C4A—C12B | 1.416 (5) |
O3—C5 | 1.430 (5) | C4A—C5 | 1.525 (5) |
O4—C5 | 1.388 (5) | C5—C6 | 1.534 (6) |
O5—C12 | 1.208 (5) | C6—C6A | 1.499 (5) |
C1—C2 | 1.386 (6) | C6A—C12A | 1.353 (6) |
C2—C3 | 1.385 (6) | C7A—C11A | 1.388 (6) |
C3—C4 | 1.379 (6) | C12A—C12B | 1.498 (5) |
C5—O3—C13 | 116.3 (3) | O3—C5—O4 | 112.9 (3) |
C5—O4—C14 | 117.3 (3) | O2—C6—C5 | 123.4 (4) |
C1—C2—C3 | 121.7 (4) | O2—C6—C6A | 124.1 (4) |
C1—C2—Br1 | 120.4 (3) | C5—C6—C6A | 112.5 (3) |
C3—C2—Br1 | 118.0 (3) | ||
C12B—C4A—C5—C6 | 33.5 (5) | C11—C11A—C12—O5 | −4.4 (7) |
O4—C5—C6—O2 | 3.7 (6) | C11A—C12—C12A—C12B | −173.0 (4) |
O2—C6—C6A—C7 | 47.0 (6) | C12—C12A—C12B—C1 | −13.3 (6) |
The analogues of angucyclines have been intensively investigated due to their biological properties (Krohn & Rohr, 1997). In order to generate a new analogue, we have prepared the title compound, (I). We have undertaken an X-ray structural determination of compound (I) to define the conformation of this system especially the conformation of the bromophenyl with respect to the substituted anthracene moiety.
In (I), the bond lengths and angles have normal values. In the aromatic rings A and D, the average C—C bond distances are 1.387 and 1.395 Å, respectively. In comparison, the C—C bond distances within the cyclohexanedione (ring B) and that of C6A—C12A are slightly shorter than in the related structure, benz[a]anthracene-7,12-dione, (II), previously studied (Kuroda et al., 1982), while the observed intramolecular interaction between C1A—H1A and O5 in (I) is a slightly longer than in (II) (2.058 Å).
The aromatic rings A and D are essentially planar, and atom Br1 deviates slightly (by 0.035 Å) from the least-square plane through ring D. The angle between these two aromatic rings is 15.1 (2)° and is much larger than in (II) benz[a]anthracene-7,12-dione (Kuroda et al., 1982), because in (I), ring C bridging between rings A and D is non-planar. The close interaction between O5 and H1A, and the non-bonded lone-pair–lone-pair repulsions of the O atoms [the non-bonded distance between O1 and O2 is 2.880 (5) Å] are two reasons for the distortions from planarity. Atom O1 lies on, while atom O5 deviates slightly by -0.121 (4) Å from the least-squares plane through ring B having a maximum deviation of 0.052 (4) Å (C12A). Atom O2 attached to ring C at C6 significantly deviates by -1.087 (4) Å, while atom C6 deviates by -0.317 (4) Å from the least-squares plane through ring C. The puckering parameters of ring C (Cremer & Pople, 1975), which adopt a half-chair conformation, are QT = 0.478 (5) Å, θ = 115.5 (6)° and ϕ2 = 275.5 (6)°.