organic compounds
Ethyl trans-12-(pyridin-4-yl)-9,10-ethanoanthracene-11-carboxylate
aCentre for Bioinformatics, Pondicherry University, Pondicherry 605 014, India, and bDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India
*Correspondence e-mail: suresh.bic@pondiuni.edu.in
In the title compound, C24H21NO2, the residues at the central ethylene bridge are trans to each other. The dihedral angles between the pyridine and benzene rings are 67.09 (6) and 61.41 (5)°. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C—H⋯O hydrogen bonds.
CCDC reference: 993524
Related literature
For the biological activity of ester derivatives, see: Bi et al. (2012); Bartzatt et al. (2004); Anadu et al. (2006). For conformation studies, see: Nardelli (1983). For a related structure, see: Gnanamani & Ramanathan (2009).
Experimental
Crystal data
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell CrysAlis RED (Oxford Diffraction, 2010); data reduction: CrysAlis RED; 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); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 993524
10.1107/S1600536814006588/bt6931sup1.cif
contains datablocks I, 2R. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006588/bt6931Isup2.hkl
Anthracene (5.34 g, 30 mmol) and 3-(pyridine-4-yl)-acrylic acid ethyl ester (4.4g, 25 mmol) were taken in round bottom flask containing distilled dichloromethane (100 ml). To this mixture anhydrous AlCl3 (6.6 g, 50 mmol) was added and stirred at 0 °C for 48 h followed by stirring the reaction mixture at room temperature for 10 h. The obtained dark black solution was poured into water, the organic layer was separated and the aqueous layer was extracted with ether. The crude material was purified through
using hexane and ethyl acetate in the ratio of 9:1 as Yield: 5.7 g, (65%).All H atoms were positioned geometrically, with C–H = 0.93–0.97 Å and constrained to ride on their parent atom,with Uiso(H) =1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.
Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell
CrysAlis RED (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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); software used to prepare material for publication: PLATON (Spek, 2009).C24H21NO2 | F(000) = 752 |
Mr = 355.42 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9754 reflections |
a = 10.1733 (19) Å | θ = 2.2–26.0° |
b = 11.156 (2) Å | µ = 0.08 mm−1 |
c = 16.361 (3) Å | T = 298 K |
β = 90.877 (3)° | Block, colourless |
V = 1856.6 (6) Å3 | 0.40 × 0.38 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur Eos diffractometer | 3664 independent reflections |
Radiation source: fine-focus sealed tube | 3105 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 15.9821 pixels mm-1 | θmax = 26.1°, θmin = 2.0° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −13→13 |
Tmin = 0.969, Tmax = 0.984 | l = −20→20 |
18677 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0561P)2 + 0.4341P] where P = (Fo2 + 2Fc2)/3 |
3664 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C24H21NO2 | V = 1856.6 (6) Å3 |
Mr = 355.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.1733 (19) Å | µ = 0.08 mm−1 |
b = 11.156 (2) Å | T = 298 K |
c = 16.361 (3) Å | 0.40 × 0.38 × 0.20 mm |
β = 90.877 (3)° |
Oxford Diffraction Xcalibur Eos diffractometer | 3664 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3105 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.984 | Rint = 0.027 |
18677 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.17 e Å−3 |
3664 reflections | Δρmin = −0.25 e Å−3 |
245 parameters |
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 | ||
C1 | 0.59145 (13) | 0.92171 (12) | 0.85231 (8) | 0.0392 (3) | |
C2 | 0.46282 (15) | 0.90612 (15) | 0.82600 (10) | 0.0502 (4) | |
H2 | 0.4091 | 0.8500 | 0.8510 | 0.060* | |
C3 | 0.41498 (17) | 0.97553 (18) | 0.76167 (12) | 0.0649 (5) | |
H3 | 0.3289 | 0.9652 | 0.7430 | 0.078* | |
C4 | 0.49392 (19) | 1.05918 (18) | 0.72543 (11) | 0.0685 (5) | |
H4 | 0.4610 | 1.1050 | 0.6823 | 0.082* | |
C5 | 0.62142 (17) | 1.07578 (16) | 0.75239 (10) | 0.0565 (4) | |
H5 | 0.6739 | 1.1334 | 0.7280 | 0.068* | |
C6 | 0.67128 (14) | 1.00685 (13) | 0.81564 (8) | 0.0407 (3) | |
C7 | 0.80801 (13) | 1.01204 (13) | 0.85311 (9) | 0.0406 (3) | |
H7 | 0.8639 | 1.0697 | 0.8248 | 0.049* | |
C8 | 0.79534 (12) | 1.04310 (11) | 0.94622 (8) | 0.0354 (3) | |
H8 | 0.8826 | 1.0330 | 0.9715 | 0.042* | |
C9 | 0.70331 (12) | 0.95000 (12) | 0.98565 (8) | 0.0341 (3) | |
H9 | 0.6244 | 0.9919 | 1.0039 | 0.041* | |
C10 | 0.66015 (13) | 0.85398 (12) | 0.92048 (8) | 0.0381 (3) | |
H10 | 0.6035 | 0.7923 | 0.9440 | 0.046* | |
C11 | 0.78412 (14) | 0.80130 (13) | 0.88616 (9) | 0.0425 (3) | |
C12 | 0.86419 (14) | 0.88680 (14) | 0.85040 (9) | 0.0442 (3) | |
C13 | 0.98283 (16) | 0.85354 (18) | 0.81716 (11) | 0.0623 (5) | |
H13 | 1.0384 | 0.9106 | 0.7947 | 0.075* | |
C14 | 1.0172 (2) | 0.7333 (2) | 0.81801 (14) | 0.0812 (7) | |
H14 | 1.0962 | 0.7096 | 0.7951 | 0.097* | |
C15 | 0.9370 (2) | 0.6489 (2) | 0.85202 (14) | 0.0788 (7) | |
H15 | 0.9615 | 0.5686 | 0.8511 | 0.095* | |
C16 | 0.82018 (18) | 0.68175 (15) | 0.88763 (11) | 0.0582 (5) | |
H16 | 0.7669 | 0.6247 | 0.9121 | 0.070* | |
C17 | 0.75608 (13) | 1.17233 (12) | 0.95790 (8) | 0.0381 (3) | |
C18 | 0.62967 (14) | 1.21560 (13) | 0.94575 (10) | 0.0475 (4) | |
H18 | 0.5619 | 1.1633 | 0.9316 | 0.057* | |
C19 | 0.60451 (16) | 1.33606 (14) | 0.95456 (11) | 0.0568 (4) | |
H19 | 0.5186 | 1.3623 | 0.9461 | 0.068* | |
C20 | 0.81530 (19) | 1.37470 (16) | 0.98575 (15) | 0.0766 (6) | |
H20 | 0.8812 | 1.4293 | 0.9993 | 0.092* | |
C21 | 0.85033 (16) | 1.25592 (14) | 0.97912 (12) | 0.0578 (4) | |
H21 | 0.9368 | 1.2323 | 0.9889 | 0.069* | |
C22 | 0.76667 (13) | 0.88949 (12) | 1.05943 (8) | 0.0371 (3) | |
C23 | 0.73365 (16) | 0.73634 (15) | 1.15837 (9) | 0.0513 (4) | |
H23A | 0.6605 | 0.7091 | 1.1909 | 0.062* | |
H23B | 0.7918 | 0.7833 | 1.1933 | 0.062* | |
C24 | 0.8059 (2) | 0.63115 (16) | 1.12588 (11) | 0.0657 (5) | |
H24A | 0.7502 | 0.5882 | 1.0881 | 0.099* | |
H24B | 0.8310 | 0.5792 | 1.1702 | 0.099* | |
H24C | 0.8831 | 0.6581 | 1.0983 | 0.099* | |
N1 | 0.69472 (15) | 1.41714 (12) | 0.97428 (11) | 0.0713 (5) | |
O1 | 0.68494 (10) | 0.81027 (9) | 1.09130 (6) | 0.0474 (3) | |
O2 | 0.87508 (11) | 0.90811 (11) | 1.08561 (7) | 0.0628 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0418 (7) | 0.0369 (7) | 0.0388 (7) | 0.0032 (6) | −0.0034 (6) | −0.0068 (6) |
C2 | 0.0442 (8) | 0.0539 (9) | 0.0522 (9) | 0.0000 (7) | −0.0074 (7) | −0.0095 (7) |
C3 | 0.0498 (9) | 0.0783 (13) | 0.0659 (11) | 0.0112 (9) | −0.0219 (8) | −0.0064 (10) |
C4 | 0.0721 (12) | 0.0729 (12) | 0.0598 (11) | 0.0150 (10) | −0.0192 (9) | 0.0128 (9) |
C5 | 0.0622 (10) | 0.0562 (10) | 0.0511 (9) | 0.0068 (8) | −0.0028 (8) | 0.0117 (8) |
C6 | 0.0442 (8) | 0.0404 (7) | 0.0374 (7) | 0.0065 (6) | −0.0001 (6) | −0.0016 (6) |
C7 | 0.0388 (7) | 0.0416 (8) | 0.0416 (7) | 0.0001 (6) | 0.0052 (6) | 0.0039 (6) |
C8 | 0.0302 (6) | 0.0331 (7) | 0.0428 (7) | −0.0015 (5) | −0.0013 (5) | 0.0013 (6) |
C9 | 0.0318 (6) | 0.0324 (7) | 0.0381 (7) | −0.0005 (5) | −0.0001 (5) | −0.0011 (5) |
C10 | 0.0406 (7) | 0.0328 (7) | 0.0408 (7) | −0.0045 (5) | −0.0042 (6) | −0.0010 (6) |
C11 | 0.0484 (8) | 0.0386 (8) | 0.0403 (7) | 0.0069 (6) | −0.0105 (6) | −0.0065 (6) |
C12 | 0.0421 (8) | 0.0510 (9) | 0.0393 (7) | 0.0092 (6) | −0.0030 (6) | −0.0072 (6) |
C13 | 0.0464 (9) | 0.0837 (13) | 0.0567 (10) | 0.0132 (9) | 0.0010 (7) | −0.0188 (9) |
C14 | 0.0606 (11) | 0.1010 (17) | 0.0817 (14) | 0.0389 (12) | −0.0100 (10) | −0.0405 (13) |
C15 | 0.0844 (14) | 0.0631 (12) | 0.0880 (14) | 0.0378 (11) | −0.0288 (12) | −0.0299 (11) |
C16 | 0.0730 (11) | 0.0420 (9) | 0.0589 (10) | 0.0140 (8) | −0.0235 (8) | −0.0121 (7) |
C17 | 0.0380 (7) | 0.0338 (7) | 0.0426 (7) | −0.0026 (6) | 0.0003 (6) | 0.0013 (6) |
C18 | 0.0387 (7) | 0.0370 (8) | 0.0668 (10) | −0.0028 (6) | −0.0044 (7) | −0.0008 (7) |
C19 | 0.0484 (9) | 0.0404 (8) | 0.0813 (12) | 0.0056 (7) | −0.0079 (8) | −0.0006 (8) |
C20 | 0.0603 (11) | 0.0398 (9) | 0.1291 (19) | −0.0094 (8) | −0.0204 (11) | −0.0138 (10) |
C21 | 0.0433 (8) | 0.0423 (9) | 0.0873 (13) | −0.0028 (7) | −0.0129 (8) | −0.0065 (8) |
C22 | 0.0372 (7) | 0.0355 (7) | 0.0385 (7) | −0.0018 (5) | −0.0013 (5) | −0.0025 (6) |
C23 | 0.0600 (9) | 0.0524 (9) | 0.0414 (8) | −0.0006 (7) | −0.0028 (7) | 0.0126 (7) |
C24 | 0.0885 (13) | 0.0532 (10) | 0.0555 (10) | 0.0116 (9) | 0.0022 (9) | 0.0108 (8) |
N1 | 0.0656 (10) | 0.0358 (7) | 0.1119 (14) | 0.0022 (7) | −0.0146 (9) | −0.0070 (8) |
O1 | 0.0444 (6) | 0.0500 (6) | 0.0476 (6) | −0.0064 (5) | −0.0044 (4) | 0.0145 (5) |
O2 | 0.0502 (7) | 0.0725 (8) | 0.0651 (7) | −0.0186 (6) | −0.0210 (5) | 0.0209 (6) |
C1—C2 | 1.382 (2) | C13—C14 | 1.386 (3) |
C1—C6 | 1.392 (2) | C13—H13 | 0.9300 |
C1—C10 | 1.5097 (19) | C14—C15 | 1.370 (3) |
C2—C3 | 1.389 (2) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.381 (3) |
C3—C4 | 1.372 (3) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.376 (3) | C17—C21 | 1.378 (2) |
C4—H4 | 0.9300 | C17—C18 | 1.385 (2) |
C5—C6 | 1.380 (2) | C18—C19 | 1.376 (2) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—C7 | 1.513 (2) | C19—N1 | 1.325 (2) |
C7—C12 | 1.510 (2) | C19—H19 | 0.9300 |
C7—C8 | 1.5695 (19) | C20—N1 | 1.326 (2) |
C7—H7 | 0.9800 | C20—C21 | 1.377 (2) |
C8—C17 | 1.5089 (19) | C20—H20 | 0.9300 |
C8—C9 | 1.5460 (17) | C21—H21 | 0.9300 |
C8—H8 | 0.9800 | C22—O2 | 1.1952 (17) |
C9—C22 | 1.5180 (18) | C22—O1 | 1.3258 (16) |
C9—C10 | 1.5693 (18) | C23—O1 | 1.4538 (17) |
C9—H9 | 0.9800 | C23—C24 | 1.487 (2) |
C10—C11 | 1.508 (2) | C23—H23A | 0.9700 |
C10—H10 | 0.9800 | C23—H23B | 0.9700 |
C11—C16 | 1.383 (2) | C24—H24A | 0.9600 |
C11—C12 | 1.389 (2) | C24—H24B | 0.9600 |
C12—C13 | 1.382 (2) | C24—H24C | 0.9600 |
C2—C1—C6 | 120.50 (14) | C13—C12—C7 | 126.37 (16) |
C2—C1—C10 | 126.33 (13) | C11—C12—C7 | 113.46 (12) |
C6—C1—C10 | 113.17 (12) | C12—C13—C14 | 118.5 (2) |
C1—C2—C3 | 119.01 (16) | C12—C13—H13 | 120.7 |
C1—C2—H2 | 120.5 | C14—C13—H13 | 120.7 |
C3—C2—H2 | 120.5 | C15—C14—C13 | 121.14 (18) |
C4—C3—C2 | 120.41 (16) | C15—C14—H14 | 119.4 |
C4—C3—H3 | 119.8 | C13—C14—H14 | 119.4 |
C2—C3—H3 | 119.8 | C14—C15—C16 | 120.74 (18) |
C3—C4—C5 | 120.54 (16) | C14—C15—H15 | 119.6 |
C3—C4—H4 | 119.7 | C16—C15—H15 | 119.6 |
C5—C4—H4 | 119.7 | C15—C16—C11 | 118.55 (19) |
C4—C5—C6 | 119.96 (17) | C15—C16—H16 | 120.7 |
C4—C5—H5 | 120.0 | C11—C16—H16 | 120.7 |
C6—C5—H5 | 120.0 | C21—C17—C18 | 116.18 (13) |
C5—C6—C1 | 119.57 (14) | C21—C17—C8 | 119.60 (13) |
C5—C6—C7 | 127.44 (14) | C18—C17—C8 | 124.18 (12) |
C1—C6—C7 | 112.98 (12) | C19—C18—C17 | 119.94 (14) |
C12—C7—C6 | 107.38 (12) | C19—C18—H18 | 120.0 |
C12—C7—C8 | 105.63 (11) | C17—C18—H18 | 120.0 |
C6—C7—C8 | 108.25 (11) | N1—C19—C18 | 124.26 (15) |
C12—C7—H7 | 111.8 | N1—C19—H19 | 117.9 |
C6—C7—H7 | 111.8 | C18—C19—H19 | 117.9 |
C8—C7—H7 | 111.8 | N1—C20—C21 | 124.93 (16) |
C17—C8—C9 | 115.20 (11) | N1—C20—H20 | 117.5 |
C17—C8—C7 | 111.08 (11) | C21—C20—H20 | 117.5 |
C9—C8—C7 | 108.42 (10) | C20—C21—C17 | 119.42 (15) |
C17—C8—H8 | 107.3 | C20—C21—H21 | 120.3 |
C9—C8—H8 | 107.3 | C17—C21—H21 | 120.3 |
C7—C8—H8 | 107.3 | O2—C22—O1 | 123.76 (13) |
C22—C9—C8 | 112.21 (10) | O2—C22—C9 | 125.88 (13) |
C22—C9—C10 | 110.35 (11) | O1—C22—C9 | 110.36 (11) |
C8—C9—C10 | 109.87 (11) | O1—C23—C24 | 110.02 (13) |
C22—C9—H9 | 108.1 | O1—C23—H23A | 109.7 |
C8—C9—H9 | 108.1 | C24—C23—H23A | 109.7 |
C10—C9—H9 | 108.1 | O1—C23—H23B | 109.7 |
C11—C10—C1 | 107.48 (11) | C24—C23—H23B | 109.7 |
C11—C10—C9 | 106.99 (11) | H23A—C23—H23B | 108.2 |
C1—C10—C9 | 106.37 (11) | C23—C24—H24A | 109.5 |
C11—C10—H10 | 111.9 | C23—C24—H24B | 109.5 |
C1—C10—H10 | 111.9 | H24A—C24—H24B | 109.5 |
C9—C10—H10 | 111.9 | C23—C24—H24C | 109.5 |
C16—C11—C12 | 120.81 (15) | H24A—C24—H24C | 109.5 |
C16—C11—C10 | 126.33 (15) | H24B—C24—H24C | 109.5 |
C12—C11—C10 | 112.86 (12) | C19—N1—C20 | 115.26 (14) |
C13—C12—C11 | 120.17 (15) | C22—O1—C23 | 117.80 (11) |
C6—C1—C2—C3 | 0.9 (2) | C16—C11—C12—C13 | −1.3 (2) |
C10—C1—C2—C3 | −179.47 (14) | C10—C11—C12—C13 | 178.93 (13) |
C1—C2—C3—C4 | −0.7 (3) | C16—C11—C12—C7 | 178.95 (13) |
C2—C3—C4—C5 | −0.2 (3) | C10—C11—C12—C7 | −0.77 (17) |
C3—C4—C5—C6 | 0.9 (3) | C6—C7—C12—C13 | 126.43 (16) |
C4—C5—C6—C1 | −0.7 (2) | C8—C7—C12—C13 | −118.21 (16) |
C4—C5—C6—C7 | 179.87 (16) | C6—C7—C12—C11 | −53.89 (15) |
C2—C1—C6—C5 | −0.2 (2) | C8—C7—C12—C11 | 61.47 (14) |
C10—C1—C6—C5 | −179.89 (13) | C11—C12—C13—C14 | 2.1 (2) |
C2—C1—C6—C7 | 179.33 (13) | C7—C12—C13—C14 | −178.20 (15) |
C10—C1—C6—C7 | −0.36 (17) | C12—C13—C14—C15 | −1.0 (3) |
C5—C6—C7—C12 | −126.13 (16) | C13—C14—C15—C16 | −1.0 (3) |
C1—C6—C7—C12 | 54.38 (15) | C14—C15—C16—C11 | 1.8 (3) |
C5—C6—C7—C8 | 120.26 (16) | C12—C11—C16—C15 | −0.6 (2) |
C1—C6—C7—C8 | −59.23 (15) | C10—C11—C16—C15 | 179.04 (15) |
C12—C7—C8—C17 | 172.86 (11) | C9—C8—C17—C21 | 135.65 (15) |
C6—C7—C8—C17 | −72.38 (14) | C7—C8—C17—C21 | −100.59 (16) |
C12—C7—C8—C9 | −59.59 (13) | C9—C8—C17—C18 | −46.84 (19) |
C6—C7—C8—C9 | 55.17 (14) | C7—C8—C17—C18 | 76.93 (17) |
C17—C8—C9—C22 | −109.03 (13) | C21—C17—C18—C19 | 0.4 (2) |
C7—C8—C9—C22 | 125.81 (12) | C8—C17—C18—C19 | −177.20 (15) |
C17—C8—C9—C10 | 127.81 (12) | C17—C18—C19—N1 | 0.2 (3) |
C7—C8—C9—C10 | 2.65 (14) | N1—C20—C21—C17 | 1.0 (4) |
C2—C1—C10—C11 | 125.88 (15) | C18—C17—C21—C20 | −0.9 (3) |
C6—C1—C10—C11 | −54.46 (15) | C8—C17—C21—C20 | 176.79 (17) |
C2—C1—C10—C9 | −119.80 (15) | C8—C9—C22—O2 | −0.6 (2) |
C6—C1—C10—C9 | 59.86 (14) | C10—C9—C22—O2 | 122.24 (16) |
C22—C9—C10—C11 | −68.66 (14) | C8—C9—C22—O1 | −179.85 (11) |
C8—C9—C10—C11 | 55.59 (14) | C10—C9—C22—O1 | −56.96 (14) |
C22—C9—C10—C1 | 176.69 (11) | C18—C19—N1—C20 | −0.1 (3) |
C8—C9—C10—C1 | −59.07 (13) | C21—C20—N1—C19 | −0.4 (3) |
C1—C10—C11—C16 | −124.66 (15) | O2—C22—O1—C23 | −4.4 (2) |
C9—C10—C11—C16 | 121.43 (15) | C9—C22—O1—C23 | 174.85 (12) |
C1—C10—C11—C12 | 55.04 (15) | C24—C23—O1—C22 | −83.74 (17) |
C9—C10—C11—C12 | −58.87 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1i | 0.93 | 2.55 | 3.2612 (18) | 134 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1i | 0.93 | 2.55 | 3.2612 (18) | 133.5 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
Acknowledgements
CRR thanks DST–FIST for the single-crystal X-ray facility at the Department of Chemistry, Pondicherry University, Pondicherry.
References
Anadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897–3905. Web of Science CrossRef PubMed CAS Google Scholar
Bartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85–94. PubMed CAS Google Scholar
Bi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832–8841. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gnanamani, E. & Ramanathan, C. R. (2009). Tetrahedron Asymmetry, 20, 2211–2215. Web of Science CSD CrossRef CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO, CrysAlis RED and CrysAlis CCD . Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Ester derivatives of many compounds exhibit a variety of pharmacological properties, for example anticancer, antitumor and antimicrobial activities (Anadu et al., 2006; Bi et al., 2012; Bartzatt et al., 2004). In view of their importance, the title compound was synthesized and we report herein on its crystal structure. In the title molecule (Fig. 1) the fused tricyclic rings [DS (C7) = 0.0051 (1) Å and D2 (C7—C6) = 0.2248 (1) Å], [DS (C7) = 0.0135 (8) Å and D2 (C7—C6) = 0.2358 (6) Å] and [DS (C7) = 0.0126 (9) Å and D2 (C7—C6) = 0.2543 (7) Å] adopt a boat conformation which can be defined by the above asymmetry parameters (Nardelli, 1983). The torsion angles H7—C7—C8—H8 = -65.81 (15)° and H8—C8—C9—H9 = 129.38 (12)°, define the ring fusions involving the fused tricyclic ring system of the ethanoanthracene moeity. The C22—O1 distance [1.326 (2) Å] shows a partial double-bond character and so the C23 maintains planarity with C22, O2 and C9. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by C18—H18···O1 hydrogen bonds (Fig. 2).