Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005767/bt6131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005767/bt6131Isup2.hkl |
CCDC reference: 185775
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.084
- Data-to-parameter ratio = 8.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.31 From the CIF: _reflns_number_total 1543 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1653 Completeness (_total/calc) 93.35% Alert C: < 95% complete General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.31 From the CIF: _reflns_number_total 1543 Count of symmetry unique reflns 1653 Completeness (_total/calc) 93.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was prepared by mixing maleic anhydride (dienophile) and anthracene (diene) in xylene in a 1:1 molar ratio. The mixture was refluxed at 403–413 K for 35 min. The resulting solution was allowed to cool to room temperature and was then placed in a water–ice bath. The yellow crystals formed were removed by filtration and washed with ethyl acetate. They were recrystallized from hot ethyl acetate, using activated charcoal to remove impurities. Colourless crystals formed upon cooling the ethyl acetate solution. The IR spectra were recorded from KBr discs, using a PE-1600 FTIR spectrometer with IRDM software. IR (cm-1): ν(δb C—H asymmetric) 3075, ν(═C—H symmetric) 3026, ν(C—H) 2968, ν(C═O asymmetric) 1862, ν(C═O symmetric) 1782, ν(C═C) 1463, ν(C—O asymmetric) 1229, ν(C—O symmetric) 1069. The 1H and 13C NMR spectra were obtained on a Bruker Advance 400 equipment. 1H NMR (400 MHz, CDCl3, M4Si; δH, p.p.m.): 3.55 (2H, s), 4.87 (2H, s), 7.34 (4H, m), 7.41 (4H, m). 13C NMR: (400 MHz, CDCl3, M4Si, δH, p.p.m.): 170.42 (C1, C2), 140.62 (C7, C12), 138.09 (C13, C18), 127.75 (C8, C11), 127.14 (C9,C10), 125.20 (C14,C17), 125.20 (C15,C16), 47.98 (C3, C4), 45.41 (C5, C6).
611 Friedel pairs merged since absolute configuration could not be determined reliably [Flack x parameter = -0.8 (12)]. H atoms were included in geometrically calculated positions and refined using a riding model. Their isotropic displacement parameters were set to 1.2 times the equivalent displacement parameters of their parent C atoms.
Data collection: SMART (Bruker, 1997-1998); cell refinement: SAINT (Bruker, 1997-1998; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
C18H12O3 | F(000) = 576 |
Mr = 276.28 | Dx = 1.381 Mg m−3 |
Monoclinic, Cc | Melting point: 261.3(1)° K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.410 (2) Å | Cell parameters from 1961 reflections |
b = 9.4020 (12) Å | θ = 2.7–28.3° |
c = 11.0939 (15) Å | µ = 0.09 mm−1 |
β = 124.235 (10)° | T = 293 K |
V = 1328.8 (3) Å3 | Prism, colorless |
Z = 4 | 0.6 × 0.4 × 0.32 mm |
Bruker SMART CCD area-detector diffractometer | 1289 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 28.3°, θmin = 2.7° |
Detector resolution: 0.75 pixels mm-1 | h = −19→18 |
ϕ and ω scans | k = −7→12 |
8380 measured reflections | l = −14→14 |
1543 independent 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0507P)2] where P = (Fo2 + 2Fc2)/3 |
1543 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.12 e Å−3 |
2 restraints | Δρmin = −0.16 e Å−3 |
C18H12O3 | V = 1328.8 (3) Å3 |
Mr = 276.28 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 15.410 (2) Å | µ = 0.09 mm−1 |
b = 9.4020 (12) Å | T = 293 K |
c = 11.0939 (15) Å | 0.6 × 0.4 × 0.32 mm |
β = 124.235 (10)° |
Bruker SMART CCD area-detector diffractometer | 1289 reflections with I > 2σ(I) |
8380 measured reflections | Rint = 0.035 |
1543 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 2 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.12 e Å−3 |
1543 reflections | Δρmin = −0.16 e Å−3 |
190 parameters |
Experimental. Siemens SMART CCD diffractometer equipped with a normal focus, 2.4 kW sealed tube X-ray source (Mo Kα radiation, λ = 0.71073 Å) operating at 40 kV and 35 mA. The data collection covered about 1.3 hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 90, 180 °) for the crystal and each exposure of 10 s covered 0.3° in ω to give a total of 1321 frames. The crystal-to-detector distance was 5.029 cm and the detector swing angle was -30°. Coverage of the unique set was over 99% complete. Crystal decay was monitored by repeating fifty frames from the initial set at the end of the data collection. The analysis of the duplicate reflections indicated that crystal decay was negligible. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.39685 (17) | 0.8228 (2) | 0.6917 (2) | 0.0847 (7) | |
O2 | 0.27881 (16) | 0.66074 (19) | 0.5445 (2) | 0.0694 (7) | |
O3 | 0.1388 (2) | 0.5462 (2) | 0.3630 (3) | 0.0962 (9) | |
C1 | 0.3132 (2) | 0.7995 (3) | 0.5837 (3) | 0.0573 (9) | |
C2 | 0.1805 (2) | 0.6570 (3) | 0.4147 (3) | 0.0623 (10) | |
C3 | 0.23194 (17) | 0.9012 (2) | 0.4725 (2) | 0.0436 (6) | |
C4 | 0.14307 (17) | 0.8055 (2) | 0.3580 (2) | 0.0459 (7) | |
C5 | 0.27666 (15) | 0.9919 (2) | 0.4012 (2) | 0.0401 (6) | |
C6 | 0.12639 (15) | 0.8282 (2) | 0.2075 (2) | 0.0431 (6) | |
C7 | 0.31173 (15) | 0.8876 (2) | 0.33241 (19) | 0.0392 (6) | |
C8 | 0.41146 (17) | 0.8754 (3) | 0.3617 (2) | 0.0501 (7) | |
C9 | 0.43059 (19) | 0.7741 (3) | 0.2895 (3) | 0.0590 (8) | |
C10 | 0.3514 (2) | 0.6849 (3) | 0.1888 (3) | 0.0593 (9) | |
C11 | 0.25095 (19) | 0.6967 (3) | 0.1576 (2) | 0.0522 (8) | |
C12 | 0.23125 (15) | 0.7989 (2) | 0.2291 (2) | 0.0402 (6) | |
C13 | 0.10372 (15) | 0.9854 (2) | 0.1736 (2) | 0.0435 (6) | |
C14 | 0.01505 (17) | 1.0439 (3) | 0.0520 (2) | 0.0557 (8) | |
C15 | 0.0080 (2) | 1.1911 (3) | 0.0349 (3) | 0.0650 (9) | |
C16 | 0.0876 (2) | 1.2770 (3) | 0.1383 (3) | 0.0626 (9) | |
C17 | 0.1758 (2) | 1.2195 (2) | 0.2607 (3) | 0.0524 (8) | |
C18 | 0.18434 (15) | 1.0732 (2) | 0.2781 (2) | 0.0417 (6) | |
H3 | 0.20670 | 0.96340 | 0.51750 | 0.0520* | |
H4 | 0.07810 | 0.82590 | 0.35130 | 0.0550* | |
H5 | 0.33360 | 1.05500 | 0.47160 | 0.0480* | |
H6 | 0.07010 | 0.76820 | 0.13130 | 0.0520* | |
H8 | 0.46510 | 0.93500 | 0.42960 | 0.0600* | |
H9 | 0.49740 | 0.76580 | 0.30870 | 0.0710* | |
H10 | 0.36540 | 0.61650 | 0.14140 | 0.0710* | |
H11 | 0.19760 | 0.63670 | 0.08970 | 0.0630* | |
H14 | −0.03910 | 0.98570 | −0.01730 | 0.0670* | |
H15 | −0.05090 | 1.23150 | −0.04700 | 0.0780* | |
H16 | 0.08190 | 1.37520 | 0.12570 | 0.0750* | |
H17 | 0.22890 | 1.27850 | 0.33080 | 0.0630* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0800 (13) | 0.0934 (15) | 0.0498 (10) | 0.0190 (11) | 0.0177 (10) | 0.0147 (10) |
O2 | 0.0925 (14) | 0.0524 (11) | 0.0678 (11) | 0.0178 (9) | 0.0479 (11) | 0.0179 (8) |
O3 | 0.130 (2) | 0.0477 (11) | 0.1142 (17) | −0.0140 (11) | 0.0707 (16) | −0.0004 (11) |
C1 | 0.0703 (16) | 0.0626 (16) | 0.0434 (12) | 0.0130 (12) | 0.0347 (13) | 0.0105 (10) |
C2 | 0.0875 (19) | 0.0466 (14) | 0.0715 (17) | −0.0001 (13) | 0.0560 (16) | 0.0044 (12) |
C3 | 0.0536 (11) | 0.0447 (11) | 0.0366 (9) | 0.0073 (10) | 0.0279 (9) | 0.0003 (9) |
C4 | 0.0526 (12) | 0.0453 (11) | 0.0497 (12) | −0.0003 (9) | 0.0347 (10) | 0.0010 (9) |
C5 | 0.0443 (10) | 0.0359 (10) | 0.0355 (9) | −0.0015 (8) | 0.0196 (8) | −0.0023 (8) |
C6 | 0.0427 (10) | 0.0460 (12) | 0.0397 (10) | −0.0072 (8) | 0.0226 (9) | −0.0069 (8) |
C7 | 0.0445 (10) | 0.0384 (10) | 0.0375 (10) | 0.0033 (8) | 0.0248 (9) | 0.0046 (8) |
C8 | 0.0459 (12) | 0.0535 (13) | 0.0504 (12) | 0.0005 (9) | 0.0268 (10) | 0.0038 (10) |
C9 | 0.0562 (13) | 0.0707 (16) | 0.0650 (14) | 0.0140 (12) | 0.0432 (12) | 0.0104 (13) |
C10 | 0.0754 (17) | 0.0605 (15) | 0.0610 (15) | 0.0125 (12) | 0.0500 (14) | −0.0015 (11) |
C11 | 0.0677 (15) | 0.0497 (13) | 0.0472 (12) | −0.0026 (10) | 0.0372 (12) | −0.0065 (10) |
C12 | 0.0455 (11) | 0.0428 (10) | 0.0371 (10) | −0.0003 (8) | 0.0261 (9) | −0.0004 (8) |
C13 | 0.0442 (10) | 0.0536 (12) | 0.0383 (9) | 0.0042 (9) | 0.0266 (9) | 0.0024 (9) |
C14 | 0.0444 (12) | 0.0843 (18) | 0.0382 (11) | 0.0133 (11) | 0.0231 (10) | 0.0045 (11) |
C15 | 0.0684 (16) | 0.0870 (19) | 0.0488 (13) | 0.0391 (14) | 0.0386 (13) | 0.0258 (13) |
C16 | 0.0810 (18) | 0.0569 (15) | 0.0664 (15) | 0.0268 (13) | 0.0515 (15) | 0.0199 (13) |
C17 | 0.0674 (14) | 0.0434 (12) | 0.0584 (13) | 0.0092 (11) | 0.0427 (12) | 0.0053 (11) |
C18 | 0.0479 (11) | 0.0445 (11) | 0.0405 (10) | 0.0057 (9) | 0.0296 (9) | 0.0036 (9) |
O1—C1 | 1.186 (4) | C13—C14 | 1.384 (3) |
O2—C1 | 1.383 (3) | C13—C18 | 1.396 (3) |
O2—C2 | 1.384 (4) | C14—C15 | 1.393 (4) |
O3—C2 | 1.188 (4) | C15—C16 | 1.375 (4) |
C1—C3 | 1.505 (4) | C16—C17 | 1.381 (4) |
C2—C4 | 1.506 (3) | C17—C18 | 1.385 (3) |
C3—C4 | 1.530 (3) | C3—H3 | 0.9803 |
C3—C5 | 1.562 (3) | C4—H4 | 0.9803 |
C4—C6 | 1.554 (3) | C5—H5 | 0.9802 |
C5—C7 | 1.517 (3) | C6—H6 | 0.9799 |
C5—C18 | 1.512 (3) | C8—H8 | 0.9296 |
C6—C12 | 1.519 (4) | C9—H9 | 0.9299 |
C6—C13 | 1.517 (3) | C10—H10 | 0.9297 |
C7—C8 | 1.385 (4) | C11—H11 | 0.9299 |
C7—C12 | 1.396 (3) | C14—H14 | 0.9300 |
C8—C9 | 1.379 (4) | C15—H15 | 0.9304 |
C9—C10 | 1.381 (4) | C16—H16 | 0.9305 |
C10—C11 | 1.388 (5) | C17—H17 | 0.9306 |
C11—C12 | 1.384 (3) | ||
O1···C8i | 3.344 (3) | C16···O3ix | 3.321 (4) |
O1···C15ii | 3.410 (3) | C8···H6iii | 2.9185 |
O1···C4iii | 3.373 (4) | C13···H3vii | 2.9734 |
O2···C7 | 3.418 (3) | C14···H10x | 3.0563 |
O2···C12 | 3.403 (3) | C15···H4vii | 2.7959 |
O3···C16iv | 3.321 (4) | C16···H9x | 2.9109 |
O1···H4iii | 2.7067 | H3···C13i | 2.9734 |
O1···H15ii | 2.6762 | H4···C15i | 2.7959 |
O2···H10v | 2.8490 | H4···O1vi | 2.7067 |
O3···H16iv | 2.7725 | H5···H8 | 2.5805 |
O3···H11v | 2.7458 | H5···H17 | 2.5735 |
C1···C12 | 3.388 (3) | H6···H11 | 2.5734 |
C2···C7 | 3.421 (4) | H6···H14 | 2.5710 |
C2···C11 | 3.597 (4) | H6···C8vi | 2.9185 |
C2···C16i | 3.547 (5) | H8···H5 | 2.5805 |
C4···C15i | 3.575 (4) | H8···H16xi | 2.5983 |
C4···O1vi | 3.373 (4) | H9···C16xii | 2.9109 |
C7···O2 | 3.418 (3) | H10···O2xiii | 2.8490 |
C7···C2 | 3.421 (4) | H10···C14xii | 3.0563 |
C8···O1vii | 3.344 (3) | H11···H6 | 2.5734 |
C11···C2 | 3.597 (4) | H11···O3xiii | 2.7458 |
C12···C1 | 3.388 (3) | H14···H6 | 2.5710 |
C12···O2 | 3.403 (3) | H15···O1viii | 2.6762 |
C15···C4vii | 3.575 (4) | H16···O3ix | 2.7725 |
C15···O1viii | 3.410 (3) | H16···H8xiv | 2.5983 |
C16···C2vii | 3.547 (5) | H17···H5 | 2.5735 |
C1—O2—C2 | 110.6 (2) | C15—C16—C17 | 120.9 (3) |
O1—C1—O2 | 119.9 (3) | C16—C17—C18 | 119.3 (2) |
O1—C1—C3 | 129.8 (3) | C5—C18—C13 | 113.37 (16) |
O2—C1—C3 | 110.3 (2) | C5—C18—C17 | 126.5 (2) |
O2—C2—O3 | 120.2 (3) | C13—C18—C17 | 120.1 (2) |
O2—C2—C4 | 110.4 (2) | C1—C3—H3 | 110.31 |
O3—C2—C4 | 129.4 (3) | C4—C3—H3 | 110.32 |
C1—C3—C4 | 104.49 (17) | C5—C3—H3 | 110.28 |
C1—C3—C5 | 111.2 (2) | C2—C4—H4 | 110.35 |
C4—C3—C5 | 110.14 (16) | C3—C4—H4 | 110.29 |
C2—C4—C3 | 104.17 (18) | C6—C4—H4 | 110.31 |
C2—C4—C6 | 111.64 (19) | C3—C5—H5 | 112.27 |
C3—C4—C6 | 109.93 (19) | C7—C5—H5 | 112.31 |
C3—C5—C7 | 106.58 (16) | C18—C5—H5 | 112.29 |
C3—C5—C18 | 105.9 (2) | C4—C6—H6 | 112.26 |
C7—C5—C18 | 107.03 (15) | C12—C6—H6 | 112.23 |
C4—C6—C12 | 106.69 (17) | C13—C6—H6 | 112.24 |
C4—C6—C13 | 106.02 (16) | C7—C8—H8 | 120.24 |
C12—C6—C13 | 106.98 (19) | C9—C8—H8 | 120.26 |
C5—C7—C8 | 126.72 (19) | C8—C9—H9 | 119.73 |
C5—C7—C12 | 113.3 (2) | C10—C9—H9 | 119.67 |
C8—C7—C12 | 119.9 (2) | C9—C10—H10 | 119.81 |
C7—C8—C9 | 119.5 (2) | C11—C10—H10 | 119.70 |
C8—C9—C10 | 120.6 (3) | C10—C11—H11 | 120.49 |
C9—C10—C11 | 120.5 (3) | C12—C11—H11 | 120.42 |
C10—C11—C12 | 119.1 (2) | C13—C14—H14 | 120.44 |
C6—C12—C7 | 113.33 (18) | C15—C14—H14 | 120.47 |
C6—C12—C11 | 126.3 (2) | C14—C15—H15 | 119.81 |
C7—C12—C11 | 120.4 (2) | C16—C15—H15 | 119.82 |
C6—C13—C14 | 126.3 (2) | C15—C16—H16 | 119.54 |
C6—C13—C18 | 113.40 (17) | C17—C16—H16 | 119.58 |
C14—C13—C18 | 120.26 (19) | C16—C17—H17 | 120.31 |
C13—C14—C15 | 119.1 (2) | C18—C17—H17 | 120.37 |
C14—C15—C16 | 120.4 (3) | ||
C2—O2—C1—O1 | −179.1 (3) | C7—C5—C18—C17 | −124.1 (3) |
C2—O2—C1—C3 | 0.3 (4) | C4—C6—C12—C7 | −59.4 (2) |
C1—O2—C2—O3 | 179.1 (3) | C4—C6—C12—C11 | 120.6 (2) |
C1—O2—C2—C4 | 0.2 (4) | C13—C6—C12—C7 | 53.7 (2) |
O1—C1—C3—C4 | 178.7 (4) | C13—C6—C12—C11 | −126.3 (2) |
O1—C1—C3—C5 | 59.9 (4) | C4—C6—C13—C14 | −122.3 (3) |
O2—C1—C3—C4 | −0.7 (3) | C4—C6—C13—C18 | 59.1 (3) |
O2—C1—C3—C5 | −119.5 (2) | C12—C6—C13—C14 | 124.1 (3) |
O2—C2—C4—C3 | −0.6 (3) | C12—C6—C13—C18 | −54.4 (2) |
O2—C2—C4—C6 | 117.9 (3) | C5—C7—C8—C9 | 179.8 (2) |
O3—C2—C4—C3 | −179.4 (4) | C12—C7—C8—C9 | −0.8 (3) |
O3—C2—C4—C6 | −60.8 (5) | C5—C7—C12—C6 | 0.8 (2) |
C1—C3—C4—C2 | 0.8 (3) | C5—C7—C12—C11 | −179.30 (18) |
C1—C3—C4—C6 | −119.0 (2) | C8—C7—C12—C6 | −178.68 (18) |
C5—C3—C4—C2 | 120.3 (2) | C8—C7—C12—C11 | 1.3 (3) |
C5—C3—C4—C6 | 0.5 (3) | C7—C8—C9—C10 | −0.1 (4) |
C1—C3—C5—C7 | 58.3 (2) | C8—C9—C10—C11 | 0.6 (4) |
C1—C3—C5—C18 | 172.10 (17) | C9—C10—C11—C12 | −0.2 (4) |
C4—C3—C5—C7 | −57.0 (2) | C10—C11—C12—C6 | 179.2 (2) |
C4—C3—C5—C18 | 56.8 (2) | C10—C11—C12—C7 | −0.8 (3) |
C2—C4—C6—C12 | −58.7 (3) | C6—C13—C14—C15 | −177.8 (3) |
C2—C4—C6—C13 | −172.4 (2) | C18—C13—C14—C15 | 0.6 (4) |
C3—C4—C6—C12 | 56.4 (2) | C6—C13—C18—C5 | 0.4 (3) |
C3—C4—C6—C13 | −57.3 (2) | C6—C13—C18—C17 | 178.8 (2) |
C3—C5—C7—C8 | −122.5 (2) | C14—C13—C18—C5 | −178.2 (2) |
C3—C5—C7—C12 | 58.1 (2) | C14—C13—C18—C17 | 0.2 (4) |
C18—C5—C7—C8 | 124.5 (2) | C13—C14—C15—C16 | −0.7 (5) |
C18—C5—C7—C12 | −54.9 (2) | C14—C15—C16—C17 | 0.0 (5) |
C3—C5—C18—C13 | −59.3 (2) | C15—C16—C17—C18 | 0.8 (5) |
C3—C5—C18—C17 | 122.5 (3) | C16—C17—C18—C5 | 177.3 (3) |
C7—C5—C18—C13 | 54.2 (3) | C16—C17—C18—C13 | −0.9 (4) |
Symmetry codes: (i) x, −y+2, z+1/2; (ii) x+1/2, y−1/2, z+1; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y−1, z; (v) x, −y+1, z+1/2; (vi) x−1/2, −y+3/2, z−1/2; (vii) x, −y+2, z−1/2; (viii) x−1/2, y+1/2, z−1; (ix) x, y+1, z; (x) x−1/2, y+1/2, z; (xi) x+1/2, −y+5/2, z+1/2; (xii) x+1/2, y−1/2, z; (xiii) x, −y+1, z−1/2; (xiv) x−1/2, −y+5/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H12O3 |
Mr | 276.28 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 15.410 (2), 9.4020 (12), 11.0939 (15) |
β (°) | 124.235 (10) |
V (Å3) | 1328.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.6 × 0.4 × 0.32 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8380, 1543, 1289 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.084, 1.03 |
No. of reflections | 1543 |
No. of parameters | 190 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.16 |
Computer programs: SMART (Bruker, 1997-1998), SAINT (Bruker, 1997-1998, SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 1998), SHELXL97 and PLATON (Spek, 1990).
O1—C1 | 1.186 (4) | C7—C8 | 1.385 (4) |
O2—C1 | 1.383 (3) | C7—C12 | 1.396 (3) |
O2—C2 | 1.384 (4) | C8—C9 | 1.379 (4) |
O3—C2 | 1.188 (4) | C9—C10 | 1.381 (4) |
C1—C3 | 1.505 (4) | C10—C11 | 1.388 (5) |
C2—C4 | 1.506 (3) | C11—C12 | 1.384 (3) |
C3—C4 | 1.530 (3) | C13—C14 | 1.384 (3) |
C3—C5 | 1.562 (3) | C13—C18 | 1.396 (3) |
C4—C6 | 1.554 (3) | C14—C15 | 1.393 (4) |
C5—C7 | 1.517 (3) | C15—C16 | 1.375 (4) |
C5—C18 | 1.512 (3) | C16—C17 | 1.381 (4) |
C6—C12 | 1.519 (4) | C17—C18 | 1.385 (3) |
C6—C13 | 1.517 (3) | ||
C1—O2—C2 | 110.6 (2) | C5—C7—C12 | 113.3 (2) |
O1—C1—O2 | 119.9 (3) | C8—C7—C12 | 119.9 (2) |
O1—C1—C3 | 129.8 (3) | C7—C8—C9 | 119.5 (2) |
O2—C1—C3 | 110.3 (2) | C8—C9—C10 | 120.6 (3) |
O2—C2—O3 | 120.2 (3) | C9—C10—C11 | 120.5 (3) |
O2—C2—C4 | 110.4 (2) | C10—C11—C12 | 119.1 (2) |
O3—C2—C4 | 129.4 (3) | C6—C12—C7 | 113.33 (18) |
C1—C3—C4 | 104.49 (17) | C6—C12—C11 | 126.3 (2) |
C1—C3—C5 | 111.2 (2) | C7—C12—C11 | 120.4 (2) |
C4—C3—C5 | 110.14 (16) | C6—C13—C14 | 126.3 (2) |
C2—C4—C3 | 104.17 (18) | C6—C13—C18 | 113.40 (17) |
C2—C4—C6 | 111.64 (19) | C14—C13—C18 | 120.26 (19) |
C3—C4—C6 | 109.93 (19) | C13—C14—C15 | 119.1 (2) |
C3—C5—C7 | 106.58 (16) | C14—C15—C16 | 120.4 (3) |
C3—C5—C18 | 105.9 (2) | C15—C16—C17 | 120.9 (3) |
C7—C5—C18 | 107.03 (15) | C16—C17—C18 | 119.3 (2) |
C4—C6—C12 | 106.69 (17) | C5—C18—C13 | 113.37 (16) |
C4—C6—C13 | 106.02 (16) | C5—C18—C17 | 126.5 (2) |
C12—C6—C13 | 106.98 (19) | C13—C18—C17 | 120.1 (2) |
C5—C7—C8 | 126.72 (19) |
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As part of a project on Diels–Alder reactions in an undergraduate organic chemistry laboratory, 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride, (I), was synthesized. The compound had been previously prepared (Bulgarovskii et al., 1979) and the crystal data and coordinates are reported in the Cambridge Structural Database (refcode BCOCAN; Allen & Kennard, 1993). Bulgarovskii et al. used benzene as the reaction and crystallization solvent, while in the present study, xylene was used for the reaction and the material was recrystallized from ethyl acetate. The reported unit-cell parameters for BCOCAN are a = 11.229 (3), b = 12.874 (3), c = 9.468 (4) Å and γ = 103.51 (2)° (space group P21/b). The cell in (I) and the cell obtained by Bulgarovskii et al., (II), are related, approximately, by the transformation aII = [001/101/010]aI. The frames collected were re-indexed in cell (II) and attempts were made to solve the structure in this cell but without success. Therefore, it was considered appropriate to describe the material under investigation as a new polymorph.
In the structure of BCOCAN, pairs of molecules related by the 21 axis face each other in an antiparallel fashion and have the planes of the anhydride rings parallel to the b axis. The central O atom of these rings points approximately in the +c and -c directions.
In contrast, as shown in Fig. 2, in the Cc polymorph, the molecules pack in chains along the c axis, with the planes of the anhydride rings approximately parallel to the b axis. The central O atoms of the anhydride rings point in the [11] and [110] directions.
In both cases, van der Waals interactions are responsible of the interactions between the molecules.