organic compounds
2,10-Dihydroxy-13-methyl-13-azatetracyclo[9.3.1.02,10.03,8]pentadeca-3(8),4,6-triene-9,15-dione
aDepartment of Physics, The Madura College, Madurai 625 011, India, bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: nilanthalakshman@yahoo.co.uk
In the title compound, C15H15NO4, the n-methylpiperidone ring adopts a chair conformation and both five-membered rings adopt a twist conformation. An intramolecular O—H⋯O hydrogen bond is observed. Inversion-related molecules are linked into R22(10) dimers by pairs of O—H⋯O hydrogen bonds. The is further stabilized by C—H⋯O hydrogen bonds.
Related literature
For the biological activity of piperidine compounds, see: Watson et al. (2000). For ring conformation details, see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809015785/ci2789sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809015785/ci2789Isup2.hkl
A mixture of 1-methyl-4-piperidinone (0.2 g, 0.002 mol), ninhydrin (0.315 g, 0.002 mol) and sarcosine (0.156 g, 0.002 mol) in methanol (30 ml) was refluxed in a water bath for 10 h. After completion of the reaction as monitored by TLC, the excess solvent was removed under vacuum and the residue was subjected to flash
using petroleum ether-ethyl acetate mixture (8:2 v/v) as to obtain crystals of title compound in 8% yield along with a other product (yield 13%, m.p. 447–448 K).The H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C-H = 0.93–0.98 Å, O-H = 0.82 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl,O).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C15H15NO4 | Z = 2 |
Mr = 273.28 | F(000) = 288 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5616 (7) Å | Cell parameters from 25 reflections |
b = 8.9033 (8) Å | θ = 2–25° |
c = 10.8091 (11) Å | µ = 0.10 mm−1 |
α = 72.764 (11)° | T = 293 K |
β = 80.486 (12)° | Block, colourless |
γ = 72.369 (11)° | 0.18 × 0.15 × 0.11 mm |
V = 660.09 (11) Å3 |
Nonius MACH-3 diffractometer | 2025 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.010 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ω–2θ scans | h = −1→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.982, Tmax = 0.989 | l = −12→12 |
2890 measured reflections | 2 standard reflections every 60 min |
2316 independent reflections | intensity decay: none |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.1839P] where P = (Fo2 + 2Fc2)/3 |
2316 reflections | (Δ/σ)max = 0.001 |
184 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C15H15NO4 | γ = 72.369 (11)° |
Mr = 273.28 | V = 660.09 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5616 (7) Å | Mo Kα radiation |
b = 8.9033 (8) Å | µ = 0.10 mm−1 |
c = 10.8091 (11) Å | T = 293 K |
α = 72.764 (11)° | 0.18 × 0.15 × 0.11 mm |
β = 80.486 (12)° |
Nonius MACH-3 diffractometer | 2025 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.010 |
Tmin = 0.982, Tmax = 0.989 | 2 standard reflections every 60 min |
2890 measured reflections | intensity decay: none |
2316 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.22 e Å−3 |
2316 reflections | Δρmin = −0.23 e Å−3 |
184 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 | ||
O1 | 0.29809 (15) | 0.41843 (13) | 0.00498 (10) | 0.0446 (3) | |
O2 | −0.04087 (14) | 0.29519 (13) | 0.08496 (10) | 0.0421 (3) | |
H2 | −0.1139 | 0.3846 | 0.0581 | 0.063* | |
O3 | −0.02584 (16) | 0.06248 (14) | 0.30007 (11) | 0.0499 (3) | |
H3 | −0.0724 | 0.0852 | 0.2313 | 0.075* | |
N1 | 0.29935 (17) | 0.38335 (15) | 0.28995 (12) | 0.0388 (3) | |
O4 | −0.19177 (16) | 0.40313 (16) | 0.45054 (11) | 0.0538 (3) | |
C8 | 0.2679 (2) | 0.30815 (17) | 0.09849 (13) | 0.0353 (3) | |
C4 | 0.2670 (2) | 0.26334 (19) | 0.41090 (14) | 0.0403 (3) | |
H4A | 0.2445 | 0.3121 | 0.4832 | 0.048* | |
H4B | 0.3768 | 0.1712 | 0.4252 | 0.048* | |
C10 | 0.3067 (2) | 0.04870 (17) | 0.24458 (14) | 0.0372 (3) | |
C7 | 0.07412 (19) | 0.30768 (16) | 0.17048 (13) | 0.0322 (3) | |
C5 | 0.0984 (2) | 0.20371 (18) | 0.40485 (13) | 0.0375 (3) | |
H5 | 0.0730 | 0.1229 | 0.4847 | 0.045* | |
C6 | 0.1144 (2) | 0.14491 (16) | 0.28236 (13) | 0.0348 (3) | |
C9 | 0.3957 (2) | 0.14516 (17) | 0.14346 (14) | 0.0372 (3) | |
C1 | −0.0622 (2) | 0.35556 (19) | 0.37706 (14) | 0.0383 (3) | |
C3 | 0.1375 (2) | 0.52059 (18) | 0.25385 (15) | 0.0406 (3) | |
H3A | 0.1661 | 0.5959 | 0.1728 | 0.049* | |
H3B | 0.0969 | 0.5788 | 0.3209 | 0.049* | |
C2 | −0.0144 (2) | 0.44610 (17) | 0.23864 (13) | 0.0362 (3) | |
H2A | −0.1220 | 0.5275 | 0.1970 | 0.043* | |
C14 | 0.5784 (2) | 0.0851 (2) | 0.09741 (16) | 0.0486 (4) | |
H14 | 0.6375 | 0.1503 | 0.0301 | 0.058* | |
C11 | 0.3986 (2) | −0.11196 (19) | 0.30063 (17) | 0.0496 (4) | |
H11 | 0.3394 | −0.1777 | 0.3674 | 0.059* | |
C12 | 0.5804 (3) | −0.1720 (2) | 0.25488 (18) | 0.0565 (5) | |
H12 | 0.6442 | −0.2794 | 0.2917 | 0.068* | |
C13 | 0.6699 (2) | −0.0751 (2) | 0.15496 (19) | 0.0572 (5) | |
H13 | 0.7927 | −0.1183 | 0.1263 | 0.069* | |
C18 | 0.4702 (3) | 0.4293 (3) | 0.2839 (2) | 0.0624 (5) | |
H18A | 0.4881 | 0.5036 | 0.2010 | 0.094* | |
H18B | 0.5737 | 0.3334 | 0.2949 | 0.094* | |
H18C | 0.4615 | 0.4811 | 0.3517 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0438 (6) | 0.0456 (6) | 0.0332 (5) | −0.0098 (5) | 0.0005 (4) | 0.0021 (5) |
O2 | 0.0419 (6) | 0.0433 (6) | 0.0416 (6) | −0.0060 (5) | −0.0146 (5) | −0.0116 (5) |
O3 | 0.0522 (7) | 0.0488 (6) | 0.0518 (7) | −0.0269 (5) | −0.0081 (5) | −0.0022 (5) |
N1 | 0.0360 (7) | 0.0438 (7) | 0.0393 (7) | −0.0155 (5) | 0.0001 (5) | −0.0116 (5) |
O4 | 0.0413 (6) | 0.0706 (8) | 0.0475 (7) | −0.0118 (6) | 0.0104 (5) | −0.0234 (6) |
C8 | 0.0365 (8) | 0.0379 (7) | 0.0285 (7) | −0.0084 (6) | −0.0037 (6) | −0.0053 (6) |
C4 | 0.0413 (8) | 0.0455 (8) | 0.0329 (7) | −0.0085 (6) | −0.0075 (6) | −0.0095 (6) |
C10 | 0.0422 (8) | 0.0343 (7) | 0.0341 (7) | −0.0068 (6) | −0.0073 (6) | −0.0090 (6) |
C7 | 0.0320 (7) | 0.0335 (7) | 0.0289 (7) | −0.0067 (6) | −0.0057 (5) | −0.0053 (6) |
C5 | 0.0396 (8) | 0.0413 (8) | 0.0268 (7) | −0.0130 (6) | 0.0003 (6) | −0.0013 (6) |
C6 | 0.0369 (8) | 0.0322 (7) | 0.0338 (7) | −0.0120 (6) | −0.0039 (6) | −0.0030 (6) |
C9 | 0.0378 (8) | 0.0387 (8) | 0.0326 (7) | −0.0050 (6) | −0.0052 (6) | −0.0101 (6) |
C1 | 0.0350 (8) | 0.0468 (8) | 0.0360 (8) | −0.0141 (6) | 0.0002 (6) | −0.0135 (6) |
C3 | 0.0491 (9) | 0.0361 (8) | 0.0370 (8) | −0.0128 (7) | −0.0008 (6) | −0.0100 (6) |
C2 | 0.0349 (7) | 0.0354 (7) | 0.0339 (7) | −0.0028 (6) | −0.0053 (6) | −0.0080 (6) |
C14 | 0.0396 (8) | 0.0557 (10) | 0.0453 (9) | −0.0037 (7) | −0.0015 (7) | −0.0160 (8) |
C11 | 0.0600 (10) | 0.0342 (8) | 0.0482 (9) | −0.0044 (7) | −0.0111 (8) | −0.0064 (7) |
C12 | 0.0617 (11) | 0.0404 (9) | 0.0592 (11) | 0.0085 (8) | −0.0191 (9) | −0.0161 (8) |
C13 | 0.0442 (9) | 0.0592 (11) | 0.0625 (11) | 0.0096 (8) | −0.0102 (8) | −0.0286 (9) |
C18 | 0.0456 (10) | 0.0723 (12) | 0.0787 (13) | −0.0281 (9) | 0.0013 (9) | −0.0244 (10) |
O1—C8 | 1.2285 (17) | C5—C1 | 1.509 (2) |
O2—C7 | 1.4171 (16) | C5—C6 | 1.537 (2) |
O2—H2 | 0.82 | C5—H5 | 0.98 |
O3—C6 | 1.4219 (17) | C9—C14 | 1.387 (2) |
O3—H3 | 0.82 | C1—C2 | 1.517 (2) |
N1—C3 | 1.453 (2) | C3—C2 | 1.541 (2) |
N1—C18 | 1.455 (2) | C3—H3A | 0.97 |
N1—C4 | 1.4613 (19) | C3—H3B | 0.97 |
O4—C1 | 1.2088 (18) | C2—H2A | 0.98 |
C8—C9 | 1.471 (2) | C14—C13 | 1.385 (3) |
C8—C7 | 1.5419 (19) | C14—H14 | 0.93 |
C4—C5 | 1.539 (2) | C11—C12 | 1.381 (3) |
C4—H4A | 0.97 | C11—H11 | 0.93 |
C4—H4B | 0.97 | C12—C13 | 1.388 (3) |
C10—C11 | 1.386 (2) | C12—H12 | 0.93 |
C10—C9 | 1.391 (2) | C13—H13 | 0.93 |
C10—C6 | 1.507 (2) | C18—H18A | 0.96 |
C7—C2 | 1.5443 (19) | C18—H18B | 0.96 |
C7—C6 | 1.5720 (18) | C18—H18C | 0.96 |
C7—O2—H2 | 109.5 | C14—C9—C8 | 128.62 (14) |
C6—O3—H3 | 109.5 | C10—C9—C8 | 109.95 (13) |
C3—N1—C18 | 114.32 (13) | O4—C1—C5 | 128.54 (14) |
C3—N1—C4 | 113.97 (12) | O4—C1—C2 | 126.94 (14) |
C18—N1—C4 | 112.86 (13) | C5—C1—C2 | 104.23 (11) |
O1—C8—C9 | 126.53 (13) | N1—C3—C2 | 105.67 (11) |
O1—C8—C7 | 124.00 (12) | N1—C3—H3A | 110.6 |
C9—C8—C7 | 108.44 (12) | C2—C3—H3A | 110.6 |
N1—C4—C5 | 110.50 (11) | N1—C3—H3B | 110.6 |
N1—C4—H4A | 109.6 | C2—C3—H3B | 110.6 |
C5—C4—H4A | 109.6 | H3A—C3—H3B | 108.7 |
N1—C4—H4B | 109.6 | C1—C2—C3 | 103.05 (11) |
C5—C4—H4B | 109.6 | C1—C2—C7 | 103.33 (11) |
H4A—C4—H4B | 108.1 | C3—C2—C7 | 109.41 (11) |
C11—C10—C9 | 120.35 (15) | C1—C2—H2A | 113.4 |
C11—C10—C6 | 128.39 (14) | C3—C2—H2A | 113.4 |
C9—C10—C6 | 111.20 (12) | C7—C2—H2A | 113.4 |
O2—C7—C8 | 108.50 (11) | C13—C14—C9 | 117.82 (16) |
O2—C7—C2 | 114.39 (11) | C13—C14—H14 | 121.1 |
C8—C7—C2 | 115.40 (12) | C9—C14—H14 | 121.1 |
O2—C7—C6 | 108.69 (11) | C12—C11—C10 | 118.30 (16) |
C8—C7—C6 | 103.21 (11) | C12—C11—H11 | 120.8 |
C2—C7—C6 | 105.84 (11) | C10—C11—H11 | 120.8 |
C1—C5—C6 | 100.91 (11) | C11—C12—C13 | 121.32 (15) |
C1—C5—C4 | 105.49 (12) | C11—C12—H12 | 119.3 |
C6—C5—C4 | 112.08 (11) | C13—C12—H12 | 119.3 |
C1—C5—H5 | 112.5 | C14—C13—C12 | 120.77 (16) |
C6—C5—H5 | 112.5 | C14—C13—H13 | 119.6 |
C4—C5—H5 | 112.5 | C12—C13—H13 | 119.6 |
O3—C6—C10 | 114.30 (12) | N1—C18—H18A | 109.5 |
O3—C6—C5 | 106.98 (11) | N1—C18—H18B | 109.5 |
C10—C6—C5 | 114.94 (12) | H18A—C18—H18B | 109.5 |
O3—C6—C7 | 111.58 (11) | N1—C18—H18C | 109.5 |
C10—C6—C7 | 104.97 (11) | H18A—C18—H18C | 109.5 |
C5—C6—C7 | 103.62 (11) | H18B—C18—H18C | 109.5 |
C14—C9—C10 | 121.43 (14) | ||
C3—N1—C4—C5 | 54.45 (16) | C6—C10—C9—C14 | 176.26 (14) |
C18—N1—C4—C5 | −172.98 (13) | C11—C10—C9—C8 | 178.38 (14) |
O1—C8—C7—O2 | 66.57 (17) | C6—C10—C9—C8 | −4.31 (17) |
C9—C8—C7—O2 | −102.49 (12) | O1—C8—C9—C14 | 4.9 (3) |
O1—C8—C7—C2 | −63.28 (18) | C7—C8—C9—C14 | 173.60 (15) |
C9—C8—C7—C2 | 127.66 (12) | O1—C8—C9—C10 | −174.49 (14) |
O1—C8—C7—C6 | −178.24 (13) | C7—C8—C9—C10 | −5.78 (16) |
C9—C8—C7—C6 | 12.70 (14) | C6—C5—C1—O4 | 138.05 (16) |
N1—C4—C5—C1 | −56.97 (15) | C4—C5—C1—O4 | −105.16 (17) |
N1—C4—C5—C6 | 51.96 (16) | C6—C5—C1—C2 | −47.81 (13) |
C11—C10—C6—O3 | −48.1 (2) | C4—C5—C1—C2 | 68.98 (13) |
C9—C10—C6—O3 | 134.84 (13) | C18—N1—C3—C2 | 168.31 (13) |
C11—C10—C6—C5 | 76.15 (19) | C4—N1—C3—C2 | −59.82 (15) |
C9—C10—C6—C5 | −100.88 (14) | O4—C1—C2—C3 | 98.33 (17) |
C11—C10—C6—C7 | −170.70 (15) | C5—C1—C2—C3 | −75.95 (13) |
C9—C10—C6—C7 | 12.27 (15) | O4—C1—C2—C7 | −147.76 (15) |
C1—C5—C6—O3 | −80.03 (13) | C5—C1—C2—C7 | 37.97 (14) |
C4—C5—C6—O3 | 168.14 (11) | N1—C3—C2—C1 | 69.03 (14) |
C1—C5—C6—C10 | 151.91 (12) | N1—C3—C2—C7 | −40.39 (14) |
C4—C5—C6—C10 | 40.09 (16) | O2—C7—C2—C1 | 106.41 (13) |
C1—C5—C6—C7 | 37.97 (13) | C8—C7—C2—C1 | −126.65 (12) |
C4—C5—C6—C7 | −73.85 (14) | C6—C7—C2—C1 | −13.22 (14) |
O2—C7—C6—O3 | −23.90 (15) | O2—C7—C2—C3 | −144.35 (12) |
C8—C7—C6—O3 | −138.96 (12) | C8—C7—C2—C3 | −17.42 (15) |
C2—C7—C6—O3 | 99.41 (13) | C6—C7—C2—C3 | 96.02 (13) |
O2—C7—C6—C10 | 100.42 (12) | C10—C9—C14—C13 | 0.3 (2) |
C8—C7—C6—C10 | −14.64 (14) | C8—C9—C14—C13 | −178.97 (15) |
C2—C7—C6—C10 | −136.28 (11) | C9—C10—C11—C12 | 1.0 (2) |
O2—C7—C6—C5 | −138.66 (11) | C6—C10—C11—C12 | −175.81 (15) |
C8—C7—C6—C5 | 106.28 (12) | C10—C11—C12—C13 | −0.3 (3) |
C2—C7—C6—C5 | −15.36 (14) | C9—C14—C13—C12 | 0.4 (3) |
C11—C10—C9—C14 | −1.1 (2) | C11—C12—C13—C14 | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 2.11 | 2.6080 (15) | 119 |
O2—H2···O1i | 0.82 | 1.90 | 2.7168 (15) | 175 |
C2—H2A···O1i | 0.98 | 2.59 | 3.3778 (18) | 137 |
C18—H18A···O1ii | 0.96 | 2.57 | 3.432 (2) | 149 |
C5—H5···O3iii | 0.98 | 2.46 | 3.4381 (18) | 173 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO4 |
Mr | 273.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5616 (7), 8.9033 (8), 10.8091 (11) |
α, β, γ (°) | 72.764 (11), 80.486 (12), 72.369 (11) |
V (Å3) | 660.09 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.18 × 0.15 × 0.11 |
Data collection | |
Diffractometer | Nonius MACH-3 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.982, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2890, 2316, 2025 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.097, 1.11 |
No. of reflections | 2316 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.23 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 2.11 | 2.6080 (15) | 119 |
O2—H2···O1i | 0.82 | 1.90 | 2.7168 (15) | 175 |
C2—H2A···O1i | 0.98 | 2.59 | 3.3778 (18) | 137 |
C18—H18A···O1ii | 0.96 | 2.57 | 3.432 (2) | 149 |
C5—H5···O3iii | 0.98 | 2.46 | 3.4381 (18) | 173 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1. |
Acknowledgements
JS and UCN thank the Management of the Madura College, Madurai, for their constant support.
References
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science 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
Watson, P. S., Jiang, B. & Scott, B. (2000). Org. Lett. 2, 3679–3681. Web of Science CrossRef PubMed CAS Google Scholar
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The piperidine ring is a distinct structural feature of a variety of alkaloid natural products and drug candidates. Watson et al. (2000) observed that during the past decade there were thousands of piperidine compounds mentioned in clinical and preclinical studies. Piperidinones, though relatively less prominent, have also been regarded as precursors of a host of biologically active compounds and natural alkaloids, prior to their conversion to piperidines. Ninhydrin is a chemical used to detect ammonia or primary and secondary amines.
In the molecule of the title compound, (Fig. 1), the six-membered ring A (N1/C4/C5/C1/C2/C3), and the five membered rings B (C1/C2/C7/C6/C5) and C(C6-C10) are not planar. Rings B and C both adopt twist conformations, as indicated by Cremer & Pople (1975) puckering parameters Q = 0.455 (2) Å and Φ = 160.4 (2)° for ring B, and Q = 0.149 (2) Å and Φ = 21.6 (6)° for ring C. Ring A adopts a chair conformation.
In the crystal structure, the molecules are linked to form dimers by intermolecular O—H···O hydrogen bonds (Table 1), generating a graph set motif of R22(10) (Fig.2). In addition, the structure is stabilized by C—H···O and van der Waals interactions.