organic compounds
H-indene-1,3-dione
of 2-hydroxy-2-(2-oxocycloheptyl)-2,3-dihydro-1aDepartment of Physics, Dr. Zakir Husain College, Ilayankudi, Sivagangai District 625 009, India, bDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and cSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
*Correspondence e-mail: vasan692000@yahoo.co.in
In the title compound, C16H16O4, the five-membered ring of the indene-1,3-dione unit adopts a twist conformation, whereas the seven-membered ring adopts a twist–chair conformation. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, weak C—H⋯O hydrogen bonds and π–π stacking [centroid-to-centroid distance = 3.7373 (8) Å] into a three-dimensional supramolecular architecture.
Keywords: crystal structure; indene-1,3-dione; hydrogen bonding; π–π stacking.
CCDC reference: 1421141
1. Related literature
For the background and potential applications of the title compound, see: Andreu et al. (2009); Fun et al. (2009); Ghalib et al. (2011); Uk Kim et al. (2004); Penthala et al. (2009); Sundar et al. (2010); Yao et al. (2006a,b).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1421141
10.1107/S2056989015016126/xu5867sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016126/xu5867Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016126/xu5867Isup3.cdx
Supporting information file. DOI: 10.1107/S2056989015016126/xu5867Isup4.cml
A mixture of cycloheptanone (1 mmol) and ninhydrin (1 mmol) was taken in a boiling tube and was subjected to microwave irradiation for 5 minutes. The progress of reaction was monitored by thin layer
after each one minute of irradiation. After completion of reaction as evident from TLC, the residue was purified by by using petroleum ether and ethyl acetate 65:35 v/v mixture as an to afford the product. The product was recrystallized from ethyl acetate.H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. | |
Fig. 2. A view of the molecular aggregation down the a axis. Ring systems and H atoms that are not involved in hydrogen bonding have been omitted for clarity. |
C16H16O4 | Dx = 1.361 Mg m−3 Dm = 1.35 Mg m−3 Dm measured by floatation method |
Mr = 272.29 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 7469 reflections |
a = 7.4131 (5) Å | θ = 2.4–27.8° |
b = 18.8596 (13) Å | µ = 0.10 mm−1 |
c = 19.0166 (13) Å | T = 294 K |
V = 2658.7 (3) Å3 | Needle, colourless |
Z = 8 | 0.30 × 0.23 × 0.18 mm |
F(000) = 1152 |
Bruker SMART APEXII CCD diffractometer | 2849 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
φ and ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.978, Tmax = 0.986 | k = −24→24 |
28734 measured reflections | l = −24→25 |
3191 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.7812P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3191 reflections | Δρmax = 0.33 e Å−3 |
185 parameters | Δρmin = −0.20 e Å−3 |
C16H16O4 | V = 2658.7 (3) Å3 |
Mr = 272.29 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.4131 (5) Å | µ = 0.10 mm−1 |
b = 18.8596 (13) Å | T = 294 K |
c = 19.0166 (13) Å | 0.30 × 0.23 × 0.18 mm |
Bruker SMART APEXII CCD diffractometer | 3191 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2849 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.986 | Rint = 0.020 |
28734 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.33 e Å−3 |
3191 reflections | Δρmin = −0.20 e Å−3 |
185 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.03172 (15) | 0.08184 (7) | 0.44453 (5) | 0.0593 (3) | |
O2 | 0.56285 (14) | 0.19613 (6) | 0.45415 (5) | 0.0525 (3) | |
O3 | 0.60520 (16) | 0.04223 (5) | 0.41294 (5) | 0.0565 (3) | |
O4 | 0.93803 (17) | 0.25552 (5) | 0.41716 (5) | 0.0570 (3) | |
C1 | 0.68387 (16) | 0.09552 (6) | 0.39677 (6) | 0.0357 (3) | |
C2 | 0.73825 (16) | 0.11650 (6) | 0.32474 (6) | 0.0343 (3) | |
C3 | 0.70883 (18) | 0.08049 (8) | 0.26203 (7) | 0.0446 (3) | |
H3 | 0.6582 | 0.0354 | 0.2617 | 0.053* | |
C4 | 0.75714 (19) | 0.11383 (9) | 0.20020 (7) | 0.0509 (4) | |
H4 | 0.7383 | 0.0908 | 0.1576 | 0.061* | |
C5 | 0.83328 (19) | 0.18099 (9) | 0.20053 (6) | 0.0487 (3) | |
H5 | 0.8608 | 0.2028 | 0.1580 | 0.058* | |
C6 | 0.86906 (18) | 0.21611 (7) | 0.26286 (6) | 0.0427 (3) | |
H6 | 0.9238 | 0.2605 | 0.2631 | 0.051* | |
C7 | 0.82010 (16) | 0.18254 (6) | 0.32509 (6) | 0.0335 (2) | |
C8 | 0.84477 (17) | 0.20639 (6) | 0.39815 (6) | 0.0355 (3) | |
C9 | 0.72848 (16) | 0.15854 (6) | 0.44602 (6) | 0.0334 (2) | |
C10 | 0.81939 (16) | 0.14094 (6) | 0.51591 (6) | 0.0343 (2) | |
H10 | 0.8396 | 0.1855 | 0.5412 | 0.041* | |
C11 | 0.70788 (19) | 0.09172 (7) | 0.56410 (7) | 0.0434 (3) | |
H11A | 0.5807 | 0.1009 | 0.5563 | 0.052* | |
H11B | 0.7312 | 0.0429 | 0.5509 | 0.052* | |
C12 | 0.7486 (3) | 0.10069 (9) | 0.64220 (7) | 0.0589 (4) | |
H12A | 0.7260 | 0.1497 | 0.6549 | 0.071* | |
H12B | 0.6645 | 0.0716 | 0.6686 | 0.071* | |
C13 | 0.9388 (3) | 0.08166 (10) | 0.66515 (8) | 0.0679 (5) | |
H13A | 0.9607 | 0.0323 | 0.6534 | 0.081* | |
H13B | 0.9459 | 0.0860 | 0.7159 | 0.081* | |
C14 | 1.0880 (2) | 0.12630 (9) | 0.63284 (8) | 0.0594 (4) | |
H14A | 1.1938 | 0.1232 | 0.6627 | 0.071* | |
H14B | 1.0494 | 0.1754 | 0.6324 | 0.071* | |
C15 | 1.1415 (2) | 0.10527 (8) | 0.55851 (8) | 0.0547 (4) | |
H15A | 1.2401 | 0.1358 | 0.5441 | 0.066* | |
H15B | 1.1886 | 0.0573 | 0.5604 | 0.066* | |
C16 | 1.00134 (17) | 0.10759 (6) | 0.50196 (7) | 0.0380 (3) | |
H2 | 0.549 (3) | 0.2103 (10) | 0.4936 (11) | 0.070 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0519 (6) | 0.0860 (8) | 0.0399 (5) | 0.0216 (5) | 0.0051 (4) | −0.0029 (5) |
O2 | 0.0512 (6) | 0.0737 (7) | 0.0326 (5) | 0.0284 (5) | 0.0016 (4) | −0.0022 (4) |
O3 | 0.0654 (7) | 0.0510 (6) | 0.0530 (6) | −0.0195 (5) | −0.0038 (5) | 0.0066 (4) |
O4 | 0.0843 (8) | 0.0484 (5) | 0.0381 (5) | −0.0224 (5) | −0.0097 (5) | −0.0021 (4) |
C1 | 0.0347 (6) | 0.0388 (6) | 0.0335 (6) | 0.0007 (4) | −0.0020 (4) | −0.0002 (4) |
C2 | 0.0325 (5) | 0.0405 (6) | 0.0298 (5) | 0.0033 (4) | −0.0018 (4) | −0.0050 (4) |
C3 | 0.0420 (7) | 0.0523 (7) | 0.0394 (7) | 0.0029 (5) | −0.0053 (5) | −0.0148 (5) |
C4 | 0.0451 (7) | 0.0768 (10) | 0.0308 (6) | 0.0108 (7) | −0.0049 (5) | −0.0160 (6) |
C5 | 0.0429 (7) | 0.0771 (9) | 0.0261 (6) | 0.0113 (6) | 0.0019 (5) | 0.0035 (6) |
C6 | 0.0418 (6) | 0.0535 (7) | 0.0327 (6) | 0.0011 (5) | 0.0009 (5) | 0.0058 (5) |
C7 | 0.0340 (5) | 0.0403 (6) | 0.0261 (5) | 0.0030 (4) | −0.0009 (4) | −0.0013 (4) |
C8 | 0.0452 (6) | 0.0337 (5) | 0.0277 (5) | 0.0015 (5) | −0.0028 (4) | −0.0005 (4) |
C9 | 0.0367 (6) | 0.0376 (5) | 0.0258 (5) | 0.0057 (4) | 0.0017 (4) | −0.0003 (4) |
C10 | 0.0399 (6) | 0.0372 (6) | 0.0257 (5) | 0.0024 (5) | 0.0003 (4) | 0.0015 (4) |
C11 | 0.0440 (7) | 0.0514 (7) | 0.0348 (6) | −0.0021 (5) | 0.0044 (5) | 0.0083 (5) |
C12 | 0.0780 (11) | 0.0668 (9) | 0.0319 (6) | −0.0066 (8) | 0.0087 (7) | 0.0102 (6) |
C13 | 0.0937 (13) | 0.0668 (10) | 0.0431 (8) | −0.0138 (9) | −0.0193 (8) | 0.0195 (7) |
C14 | 0.0743 (10) | 0.0544 (8) | 0.0494 (8) | −0.0069 (7) | −0.0244 (7) | 0.0063 (6) |
C15 | 0.0475 (8) | 0.0568 (8) | 0.0597 (9) | 0.0069 (6) | −0.0157 (7) | −0.0008 (7) |
C16 | 0.0379 (6) | 0.0400 (6) | 0.0360 (6) | 0.0004 (5) | 0.0017 (5) | 0.0066 (5) |
O1—C16 | 1.2163 (16) | C9—C10 | 1.5267 (15) |
O2—C9 | 1.4262 (14) | C10—C16 | 1.5118 (17) |
O2—H2 | 0.80 (2) | C10—C11 | 1.5442 (16) |
O3—C1 | 1.2018 (15) | C10—H10 | 0.9800 |
O4—C8 | 1.2113 (15) | C11—C12 | 1.5249 (18) |
C1—C2 | 1.4818 (16) | C11—H11A | 0.9700 |
C1—C9 | 1.5489 (16) | C11—H11B | 0.9700 |
C2—C7 | 1.3856 (17) | C12—C13 | 1.519 (3) |
C2—C3 | 1.3894 (16) | C12—H12A | 0.9700 |
C3—C4 | 1.381 (2) | C12—H12B | 0.9700 |
C3—H3 | 0.9300 | C13—C14 | 1.520 (3) |
C4—C5 | 1.387 (2) | C13—H13A | 0.9700 |
C4—H4 | 0.9300 | C13—H13B | 0.9700 |
C5—C6 | 1.3833 (18) | C14—C15 | 1.521 (2) |
C5—H5 | 0.9300 | C14—H14A | 0.9700 |
C6—C7 | 1.3904 (16) | C14—H14B | 0.9700 |
C6—H6 | 0.9300 | C15—C16 | 1.4961 (19) |
C7—C8 | 1.4718 (15) | C15—H15A | 0.9700 |
C8—C9 | 1.5448 (16) | C15—H15B | 0.9700 |
C9—O2—H2 | 112.0 (14) | C9—C10—H10 | 107.9 |
O3—C1—C2 | 126.28 (11) | C11—C10—H10 | 107.9 |
O3—C1—C9 | 126.20 (11) | C12—C11—C10 | 113.91 (12) |
C2—C1—C9 | 107.22 (9) | C12—C11—H11A | 108.8 |
C7—C2—C3 | 120.82 (11) | C10—C11—H11A | 108.8 |
C7—C2—C1 | 110.77 (9) | C12—C11—H11B | 108.8 |
C3—C2—C1 | 128.33 (12) | C10—C11—H11B | 108.8 |
C4—C3—C2 | 117.88 (13) | H11A—C11—H11B | 107.7 |
C4—C3—H3 | 121.1 | C13—C12—C11 | 115.93 (14) |
C2—C3—H3 | 121.1 | C13—C12—H12A | 108.3 |
C3—C4—C5 | 121.17 (12) | C11—C12—H12A | 108.3 |
C3—C4—H4 | 119.4 | C13—C12—H12B | 108.3 |
C5—C4—H4 | 119.4 | C11—C12—H12B | 108.3 |
C6—C5—C4 | 121.29 (12) | H12A—C12—H12B | 107.4 |
C6—C5—H5 | 119.4 | C12—C13—C14 | 115.37 (13) |
C4—C5—H5 | 119.4 | C12—C13—H13A | 108.4 |
C5—C6—C7 | 117.47 (13) | C14—C13—H13A | 108.4 |
C5—C6—H6 | 121.3 | C12—C13—H13B | 108.4 |
C7—C6—H6 | 121.3 | C14—C13—H13B | 108.4 |
C2—C7—C6 | 121.30 (11) | H13A—C13—H13B | 107.5 |
C2—C7—C8 | 109.50 (10) | C13—C14—C15 | 114.90 (14) |
C6—C7—C8 | 129.20 (11) | C13—C14—H14A | 108.5 |
O4—C8—C7 | 125.90 (11) | C15—C14—H14A | 108.5 |
O4—C8—C9 | 126.13 (10) | C13—C14—H14B | 108.5 |
C7—C8—C9 | 107.96 (9) | C15—C14—H14B | 108.5 |
O2—C9—C10 | 113.19 (9) | H14A—C14—H14B | 107.5 |
O2—C9—C8 | 104.70 (9) | C16—C15—C14 | 118.64 (13) |
C10—C9—C8 | 113.18 (10) | C16—C15—H15A | 107.7 |
O2—C9—C1 | 105.26 (10) | C14—C15—H15A | 107.7 |
C10—C9—C1 | 116.99 (9) | C16—C15—H15B | 107.7 |
C8—C9—C1 | 102.19 (9) | C14—C15—H15B | 107.7 |
C16—C10—C9 | 109.36 (9) | H15A—C15—H15B | 107.1 |
C16—C10—C11 | 109.37 (9) | O1—C16—C15 | 120.34 (12) |
C9—C10—C11 | 114.26 (10) | O1—C16—C10 | 119.27 (11) |
C16—C10—H10 | 107.9 | C15—C16—C10 | 120.38 (11) |
O3—C1—C2—C7 | 177.60 (13) | O3—C1—C9—O2 | −76.24 (15) |
C9—C1—C2—C7 | 3.64 (13) | C2—C1—C9—O2 | 97.72 (11) |
O3—C1—C2—C3 | 0.9 (2) | O3—C1—C9—C10 | 50.41 (17) |
C9—C1—C2—C3 | −173.10 (12) | C2—C1—C9—C10 | −135.63 (10) |
C7—C2—C3—C4 | −2.52 (19) | O3—C1—C9—C8 | 174.60 (13) |
C1—C2—C3—C4 | 173.93 (12) | C2—C1—C9—C8 | −11.44 (12) |
C2—C3—C4—C5 | 0.3 (2) | O2—C9—C10—C16 | −174.64 (10) |
C3—C4—C5—C6 | 2.1 (2) | C8—C9—C10—C16 | −55.70 (12) |
C4—C5—C6—C7 | −2.2 (2) | C1—C9—C10—C16 | 62.72 (13) |
C3—C2—C7—C6 | 2.51 (18) | O2—C9—C10—C11 | 62.41 (14) |
C1—C2—C7—C6 | −174.52 (11) | C8—C9—C10—C11 | −178.65 (10) |
C3—C2—C7—C8 | −176.47 (11) | C1—C9—C10—C11 | −60.24 (13) |
C1—C2—C7—C8 | 6.50 (14) | C16—C10—C11—C12 | 83.76 (14) |
C5—C6—C7—C2 | −0.13 (18) | C9—C10—C11—C12 | −153.30 (12) |
C5—C6—C7—C8 | 178.63 (12) | C10—C11—C12—C13 | −63.91 (18) |
C2—C7—C8—O4 | 166.80 (13) | C11—C12—C13—C14 | 62.5 (2) |
C6—C7—C8—O4 | −12.1 (2) | C12—C13—C14—C15 | −79.9 (2) |
C2—C7—C8—C9 | −14.11 (13) | C13—C14—C15—C16 | 59.78 (19) |
C6—C7—C8—C9 | 167.02 (12) | C14—C15—C16—O1 | −169.58 (14) |
O4—C8—C9—O2 | 84.79 (15) | C14—C15—C16—C10 | 9.5 (2) |
C7—C8—C9—O2 | −94.30 (11) | C9—C10—C16—O1 | −19.61 (16) |
O4—C8—C9—C10 | −38.94 (17) | C11—C10—C16—O1 | 106.21 (14) |
C7—C8—C9—C10 | 141.98 (10) | C9—C10—C16—C15 | 161.33 (12) |
O4—C8—C9—C1 | −165.63 (13) | C11—C10—C16—C15 | −72.85 (15) |
C7—C8—C9—C1 | 15.28 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.80 (2) | 1.99 (2) | 2.7707 (13) | 163 (2) |
C4—H4···O1ii | 0.93 | 2.48 | 3.2758 (17) | 144 |
C15—H15B···O3iii | 0.97 | 2.47 | 3.3998 (19) | 160 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1/2, y, −z+1/2; (iii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.80 (2) | 1.99 (2) | 2.7707 (13) | 163 (2) |
C4—H4···O1ii | 0.93 | 2.48 | 3.2758 (17) | 143.9 |
C15—H15B···O3iii | 0.97 | 2.47 | 3.3998 (19) | 159.6 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1/2, y, −z+1/2; (iii) −x+2, −y, −z+1. |
Acknowledgements
The authors thank the Sophisticated Analytical Instrumentation Facility (SAIF), Indian Institute of Technology, Chennai, for the
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In the continuation of studies of ninhydrin reactions viz. 2-acetonyl-2-hydroxyindan-1,3-dione (Fun et al., 2009), rac-2-(2-amino-4-pxp-4,5-dihydro-1,3-thiazol-5-yl)-2- hydroxyindane-1,3-dione (Penthala et al., 2009), rac-2-hydroxy-2-(2-oxocyclopentyl)-1H-indene- 1,3(2H)-dione (Sundar et al., 2010), 2-hydroxy-2- (3-oxobutan-2-yl)indan-1,3-dione, we have undertaken the structural analysis of the title compound, the indene-1,3(2H)-dione moiety belongs to an important class of luminescent materials which is used as a strong electron acceptor in organic light-emitting diodes (Yao et al., 2006a,b; Andreu et al., 2009; Kim et al., 2004). The derivatives of indandione is a promising materials in the field of photonics. It is also used in the first stage of forensic identification of latent fingerprints.
The measure of angle strain is 5.65° which is comparable with calculated crystal structure data value of 6.5°.
The title compound 2-hydroxy-2-(2-oxocycloheptyl)-2,3-dihydro-1H-indene-1,3-dione crystallizes in orthorhombic space group Pbca. The five-membered ring adopts twist conformation on C8—C9 with Q = 0.1502 Å and φ = 302.24°. In the crystal structure, molecules are linked by intermolecular O—H···O and C—H···O hydrogen bonds. The symmetry related six-membered spiro rings show π-π interactions with distance of 3.7373 (8) Å (Fig. 2).
The O—H···O hydrogen bonding form a infinite linear hydrogen bonding chain C(11) extending along a axis.
The mean plane of oxocycloheptyl and fused ring of indene make an angle of 61.945 °. The substituent oxygen O1 deviates from the mean plane of oxocycloheptyl ring by -0.9121 Å