organic compounds
1-(4-Isopropylphenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhj@njut.edu.cn
In the molecule of the title compound, C19H22N2O2, the pyrazolidinone ring has an with the C atom attached to the 4-methoxyphenyl ring displaced by 0.354 (3) Å from the plane of the other ring atoms. The 4-isopropylphenyl ring is oriented with respect to the 4-methoxyphenyl ring at a dihedral angle of 88.94 (3)°. Intramolecular C—H⋯N hydrogen bonds result in the formation of two planar five-membered rings, which are oriented with respect to the adjacent 4-isopropylphenyl and 4-methoxyphenyl rings at dihedral angles of 4.05 (3) and 0.50 (3)°, respectively. In the intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.
Related literature
For general background, see: Menozzi et al. (1990); Brooks et al. (1990); Greenwood et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808009823/hk2451sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009823/hk2451Isup2.hkl
For the preparation of the title compound, ethanolamine (4 ml) and n-butanol (20 ml) were added to a solution of sodium (40 mmol) in anhydrous methanol (9 mol). Then, the methanol was removed by distillation and 3-(4-methylphenyl) acrylate was added. The mixture was refluxed for 1 h at the temperature above 373 K, after which isopropyphenyl hydrazine (4 ml) was added. The reactants were refluxed for a further 10 h, left to cool to room temperature, and then acidified with acetic acid (36%), allowed to stand, filtered, and the filter cake was crystallized from ethyl acetate to give the title compound (m.p. 435-437 K). It was crystallized by the slow evaporation of an ethyl acetate solution.
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C19H22N2O2 | F(000) = 664 |
Mr = 310.39 | Dx = 1.207 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 14.737 (3) Å | θ = 9–13° |
b = 7.1490 (14) Å | µ = 0.08 mm−1 |
c = 17.493 (4) Å | T = 294 K |
β = 112.03 (3)° | Block, colorless |
V = 1708.4 (7) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1835 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω/2θ scans | h = −18→16 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→8 |
Tmin = 0.969, Tmax = 0.984 | l = 0→21 |
3472 measured reflections | 3 standard reflections every 120 min |
3340 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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.008P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3 |
3340 reflections | (Δ/σ)max < 0.001 |
202 parameters | Δρmax = 0.38 e Å−3 |
1 restraint | Δρmin = −0.78 e Å−3 |
C19H22N2O2 | V = 1708.4 (7) Å3 |
Mr = 310.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.737 (3) Å | µ = 0.08 mm−1 |
b = 7.1490 (14) Å | T = 294 K |
c = 17.493 (4) Å | 0.40 × 0.30 × 0.20 mm |
β = 112.03 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1835 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.052 |
Tmin = 0.969, Tmax = 0.984 | 3 standard reflections every 120 min |
3472 measured reflections | intensity decay: none |
3340 independent reflections |
R[F2 > 2σ(F2)] = 0.078 | 1 restraint |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.38 e Å−3 |
3340 reflections | Δρmin = −0.78 e Å−3 |
202 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 > 2sigma(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 | 0.52570 (18) | 0.7545 (4) | 1.04046 (16) | 0.0569 (7) | |
N1 | 0.2835 (2) | 0.9106 (4) | 0.97974 (18) | 0.0486 (8) | |
N2 | 0.3849 (2) | 0.9266 (4) | 0.99532 (18) | 0.0508 (8) | |
H2A | 0.4104 | 1.0278 | 0.9859 | 0.061* | |
C1 | 0.0956 (5) | 1.2768 (9) | 1.2266 (4) | 0.117 (2) | |
H1A | 0.0772 | 1.3608 | 1.2611 | 0.176* | |
H1B | 0.1383 | 1.1821 | 1.2601 | 0.176* | |
H1C | 0.0380 | 1.2191 | 1.1876 | 0.176* | |
O2 | 0.0840 (2) | 0.3384 (4) | 0.67816 (16) | 0.0656 (8) | |
C2 | 0.0897 (4) | 1.5470 (7) | 1.1350 (3) | 0.091 | |
H2B | 0.0705 | 1.6238 | 1.1714 | 0.136* | |
H2C | 0.0323 | 1.5035 | 1.0906 | 0.136* | |
H2D | 0.1294 | 1.6189 | 1.1131 | 0.136* | |
C3 | 0.1471 (4) | 1.3827 (7) | 1.1817 (3) | 0.0881 (16) | |
H3A | 0.2057 | 1.4352 | 1.2244 | 0.106* | |
C4 | 0.1840 (3) | 1.2577 (6) | 1.1290 (3) | 0.0657 (11) | |
C5 | 0.1216 (3) | 1.1481 (7) | 1.0656 (3) | 0.0792 (14) | |
H5A | 0.0549 | 1.1507 | 1.0548 | 0.095* | |
C6 | 0.1557 (3) | 1.0349 (6) | 1.0180 (3) | 0.0684 (12) | |
H6A | 0.1116 | 0.9649 | 0.9754 | 0.082* | |
C7 | 0.2539 (3) | 1.0251 (5) | 1.0332 (2) | 0.0467 (9) | |
C8 | 0.3165 (3) | 1.1359 (5) | 1.0951 (2) | 0.0538 (10) | |
H8A | 0.3831 | 1.1348 | 1.1053 | 0.065* | |
C9 | 0.2817 (3) | 1.2487 (6) | 1.1424 (3) | 0.0626 (11) | |
H9A | 0.3257 | 1.3203 | 1.1843 | 0.075* | |
C10 | 0.2671 (3) | 0.7054 (5) | 0.9853 (2) | 0.0485 (9) | |
H10A | 0.2251 | 0.6878 | 1.0169 | 0.058* | |
C11 | 0.3691 (3) | 0.6265 (5) | 1.0361 (2) | 0.0522 (10) | |
H11A | 0.3780 | 0.6123 | 1.0936 | 0.063* | |
H11B | 0.3792 | 0.5064 | 1.0147 | 0.063* | |
C12 | 0.4378 (3) | 0.7731 (5) | 1.0257 (2) | 0.0473 (9) | |
C13 | 0.2185 (3) | 0.6143 (5) | 0.9026 (2) | 0.0489 (9) | |
C14 | 0.1919 (3) | 0.7046 (6) | 0.8282 (2) | 0.0556 (10) | |
H14A | 0.2044 | 0.8320 | 0.8274 | 0.067* | |
C15 | 0.1471 (3) | 0.6114 (6) | 0.7545 (2) | 0.0583 (11) | |
H15A | 0.1289 | 0.6768 | 0.7050 | 0.070* | |
C16 | 0.1289 (3) | 0.4205 (6) | 0.7537 (2) | 0.0544 (10) | |
C17 | 0.1560 (3) | 0.3291 (6) | 0.8282 (2) | 0.0691 (12) | |
H17A | 0.1439 | 0.2017 | 0.8292 | 0.083* | |
C18 | 0.2002 (3) | 0.4224 (5) | 0.9003 (2) | 0.0636 (12) | |
H18A | 0.2188 | 0.3565 | 0.9497 | 0.076* | |
C19 | 0.0726 (3) | 0.1427 (6) | 0.6765 (3) | 0.0721 (13) | |
H19A | 0.0399 | 0.1019 | 0.6206 | 0.108* | |
H19B | 0.0344 | 0.1084 | 0.7083 | 0.108* | |
H19C | 0.1358 | 0.0845 | 0.6996 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0495 (16) | 0.0490 (16) | 0.0681 (17) | 0.0004 (13) | 0.0174 (13) | 0.0023 (13) |
N1 | 0.0495 (18) | 0.0428 (17) | 0.0569 (19) | −0.0016 (15) | 0.0238 (15) | 0.0036 (15) |
N2 | 0.0493 (18) | 0.0411 (17) | 0.068 (2) | −0.0024 (15) | 0.0287 (16) | 0.0015 (16) |
C1 | 0.158 (6) | 0.112 (5) | 0.131 (5) | 0.002 (4) | 0.110 (5) | −0.012 (4) |
O2 | 0.0709 (19) | 0.0627 (19) | 0.0500 (16) | −0.0031 (15) | 0.0077 (14) | −0.0046 (14) |
C2 | 0.091 | 0.091 | 0.091 | 0.000 | 0.034 | 0.000 |
C3 | 0.098 (4) | 0.083 (4) | 0.105 (4) | 0.008 (3) | 0.064 (3) | −0.003 (3) |
C4 | 0.071 (3) | 0.059 (3) | 0.078 (3) | −0.003 (2) | 0.042 (2) | −0.006 (2) |
C5 | 0.051 (2) | 0.092 (4) | 0.105 (4) | 0.001 (3) | 0.040 (3) | −0.009 (3) |
C6 | 0.054 (2) | 0.068 (3) | 0.089 (3) | −0.016 (2) | 0.034 (2) | −0.020 (3) |
C7 | 0.047 (2) | 0.042 (2) | 0.053 (2) | −0.0051 (17) | 0.0211 (18) | −0.0005 (18) |
C8 | 0.051 (2) | 0.055 (2) | 0.055 (2) | −0.0008 (19) | 0.0204 (19) | 0.011 (2) |
C9 | 0.074 (3) | 0.057 (3) | 0.061 (3) | −0.007 (2) | 0.029 (2) | −0.008 (2) |
C10 | 0.051 (2) | 0.044 (2) | 0.055 (2) | −0.0040 (18) | 0.0254 (18) | −0.0009 (18) |
C11 | 0.063 (2) | 0.041 (2) | 0.046 (2) | −0.0069 (19) | 0.0129 (18) | −0.0012 (17) |
C12 | 0.056 (2) | 0.044 (2) | 0.042 (2) | −0.0043 (19) | 0.0191 (17) | −0.0029 (17) |
C13 | 0.047 (2) | 0.045 (2) | 0.050 (2) | −0.0016 (18) | 0.0125 (17) | 0.0050 (18) |
C14 | 0.057 (2) | 0.045 (2) | 0.058 (2) | −0.0012 (19) | 0.014 (2) | 0.0083 (19) |
C15 | 0.065 (3) | 0.056 (3) | 0.046 (2) | 0.001 (2) | 0.0116 (19) | 0.008 (2) |
C16 | 0.045 (2) | 0.061 (3) | 0.049 (2) | −0.0008 (19) | 0.0084 (17) | 0.000 (2) |
C17 | 0.089 (3) | 0.046 (2) | 0.057 (3) | −0.012 (2) | 0.010 (2) | 0.001 (2) |
C18 | 0.090 (3) | 0.042 (2) | 0.049 (2) | −0.008 (2) | 0.014 (2) | 0.0026 (19) |
C19 | 0.075 (3) | 0.069 (3) | 0.067 (3) | −0.017 (3) | 0.020 (2) | −0.017 (2) |
O1—C12 | 1.229 (4) | C7—C8 | 1.379 (5) |
N1—N2 | 1.418 (4) | C8—C9 | 1.383 (5) |
N1—C7 | 1.429 (4) | C8—H8A | 0.9300 |
N1—C10 | 1.496 (4) | C9—H9A | 0.9300 |
N2—C12 | 1.336 (4) | C10—C13 | 1.501 (5) |
N2—H2A | 0.8600 | C10—C11 | 1.538 (5) |
C1—C3 | 1.488 (6) | C10—H10A | 0.9800 |
C1—H1A | 0.9600 | C11—C12 | 1.515 (5) |
C1—H1B | 0.9600 | C11—H11A | 0.9700 |
C1—H1C | 0.9600 | C11—H11B | 0.9700 |
O2—C16 | 1.368 (4) | C13—C14 | 1.372 (5) |
O2—C19 | 1.407 (5) | C13—C18 | 1.396 (5) |
C2—C3 | 1.498 (6) | C14—C15 | 1.380 (5) |
C2—H2B | 0.9600 | C14—H14A | 0.9300 |
C2—H2C | 0.9600 | C15—C16 | 1.390 (5) |
C2—H2D | 0.9600 | C15—H15A | 0.9300 |
C3—C4 | 1.524 (6) | C16—C17 | 1.378 (5) |
C3—H3A | 0.9800 | C17—C18 | 1.358 (5) |
C4—C9 | 1.370 (5) | C17—H17A | 0.9300 |
C4—C5 | 1.386 (6) | C18—H18A | 0.9300 |
C5—C6 | 1.384 (6) | C19—H19A | 0.9600 |
C5—H5A | 0.9300 | C19—H19B | 0.9600 |
C6—C7 | 1.372 (5) | C19—H19C | 0.9600 |
C6—H6A | 0.9300 | ||
N2—N1—C7 | 112.7 (3) | C4—C9—H9A | 119.1 |
N2—N1—C10 | 104.5 (3) | C8—C9—H9A | 119.1 |
C7—N1—C10 | 115.0 (3) | N1—C10—C13 | 113.1 (3) |
C12—N2—N1 | 115.2 (3) | N1—C10—C11 | 104.5 (3) |
C12—N2—H2A | 122.4 | C13—C10—C11 | 114.0 (3) |
N1—N2—H2A | 122.4 | N1—C10—H10A | 108.3 |
C3—C1—H1A | 109.5 | C13—C10—H10A | 108.3 |
C3—C1—H1B | 109.5 | C11—C10—H10A | 108.3 |
H1A—C1—H1B | 109.5 | C12—C11—C10 | 103.3 (3) |
C3—C1—H1C | 109.5 | C12—C11—H11A | 111.1 |
H1A—C1—H1C | 109.5 | C10—C11—H11A | 111.1 |
H1B—C1—H1C | 109.5 | C12—C11—H11B | 111.1 |
C16—O2—C19 | 117.2 (3) | C10—C11—H11B | 111.1 |
C3—C2—H2B | 109.5 | H11A—C11—H11B | 109.1 |
C3—C2—H2C | 109.5 | O1—C12—N2 | 125.8 (3) |
H2B—C2—H2C | 109.5 | O1—C12—C11 | 126.8 (3) |
C3—C2—H2D | 109.5 | N2—C12—C11 | 107.4 (3) |
H2B—C2—H2D | 109.5 | C14—C13—C18 | 116.9 (4) |
H2C—C2—H2D | 109.5 | C14—C13—C10 | 125.0 (3) |
C1—C3—C2 | 113.1 (4) | C18—C13—C10 | 118.1 (3) |
C1—C3—C4 | 112.9 (4) | C13—C14—C15 | 121.7 (4) |
C2—C3—C4 | 112.7 (4) | C13—C14—H14A | 119.1 |
C1—C3—H3A | 105.8 | C15—C14—H14A | 119.1 |
C2—C3—H3A | 105.8 | C14—C15—C16 | 120.4 (4) |
C4—C3—H3A | 105.8 | C14—C15—H15A | 119.8 |
C9—C4—C5 | 116.7 (4) | C16—C15—H15A | 119.8 |
C9—C4—C3 | 121.0 (4) | O2—C16—C17 | 125.1 (4) |
C5—C4—C3 | 122.4 (4) | O2—C16—C15 | 116.9 (4) |
C6—C5—C4 | 122.0 (4) | C17—C16—C15 | 118.0 (4) |
C6—C5—H5A | 119.0 | C18—C17—C16 | 121.0 (4) |
C4—C5—H5A | 119.0 | C18—C17—H17A | 119.5 |
C7—C6—C5 | 120.5 (4) | C16—C17—H17A | 119.5 |
C7—C6—H6A | 119.8 | C17—C18—C13 | 122.0 (4) |
C5—C6—H6A | 119.8 | C17—C18—H18A | 119.0 |
C6—C7—C8 | 118.0 (4) | C13—C18—H18A | 119.0 |
C6—C7—N1 | 117.5 (3) | O2—C19—H19A | 109.5 |
C8—C7—N1 | 124.4 (3) | O2—C19—H19B | 109.5 |
C7—C8—C9 | 121.0 (4) | H19A—C19—H19B | 109.5 |
C7—C8—H8A | 119.5 | O2—C19—H19C | 109.5 |
C9—C8—H8A | 119.5 | H19A—C19—H19C | 109.5 |
C4—C9—C8 | 121.7 (4) | H19B—C19—H19C | 109.5 |
C7—N1—N2—C12 | 112.7 (3) | C7—N1—C10—C11 | −103.1 (3) |
C10—N1—N2—C12 | −12.9 (4) | N1—C10—C11—C12 | −21.7 (4) |
C1—C3—C4—C9 | −120.1 (5) | C13—C10—C11—C12 | 102.3 (3) |
C2—C3—C4—C9 | 110.2 (5) | N1—N2—C12—O1 | 176.9 (3) |
C1—C3—C4—C5 | 59.8 (7) | N1—N2—C12—C11 | −1.5 (4) |
C2—C3—C4—C5 | −69.8 (6) | C10—C11—C12—O1 | −163.7 (4) |
C9—C4—C5—C6 | 0.0 (7) | C10—C11—C12—N2 | 14.7 (4) |
C3—C4—C5—C6 | −180.0 (4) | N1—C10—C13—C14 | 0.7 (5) |
C4—C5—C6—C7 | 1.2 (8) | C11—C10—C13—C14 | −118.5 (4) |
C5—C6—C7—C8 | −2.2 (6) | N1—C10—C13—C18 | 179.5 (4) |
C5—C6—C7—N1 | −177.8 (4) | C11—C10—C13—C18 | 60.3 (5) |
N2—N1—C7—C6 | 173.6 (3) | C18—C13—C14—C15 | 1.4 (6) |
C10—N1—C7—C6 | −66.8 (5) | C10—C13—C14—C15 | −179.8 (4) |
N2—N1—C7—C8 | −1.8 (5) | C13—C14—C15—C16 | −1.0 (6) |
C10—N1—C7—C8 | 117.9 (4) | C19—O2—C16—C17 | −5.9 (6) |
C6—C7—C8—C9 | 2.1 (6) | C19—O2—C16—C15 | 174.9 (4) |
N1—C7—C8—C9 | 177.4 (4) | C14—C15—C16—O2 | 179.8 (3) |
C5—C4—C9—C8 | 0.0 (7) | C14—C15—C16—C17 | 0.6 (6) |
C3—C4—C9—C8 | 179.9 (4) | O2—C16—C17—C18 | −179.9 (4) |
C7—C8—C9—C4 | −1.1 (6) | C15—C16—C17—C18 | −0.7 (7) |
N2—N1—C10—C13 | −103.6 (3) | C16—C17—C18—C13 | 1.2 (7) |
C7—N1—C10—C13 | 132.3 (3) | C14—C13—C18—C17 | −1.5 (7) |
N2—N1—C10—C11 | 21.0 (4) | C10—C13—C18—C17 | 179.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 1.96 | 2.819 (4) | 175 |
C8—H8A···N2 | 0.93 | 2.44 | 2.761 (5) | 100 |
C14—H14A···N1 | 0.93 | 2.54 | 2.887 (5) | 102 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C19H22N2O2 |
Mr | 310.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 14.737 (3), 7.1490 (14), 17.493 (4) |
β (°) | 112.03 (3) |
V (Å3) | 1708.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.969, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3472, 3340, 1835 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.163, 1.06 |
No. of reflections | 3340 |
No. of parameters | 202 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.78 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 1.96 | 2.819 (4) | 175.0 |
C8—H8A···N2 | 0.93 | 2.44 | 2.761 (5) | 100.0 |
C14—H14A···N1 | 0.93 | 2.54 | 2.887 (5) | 102.0 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
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Pyrazolidin-3-one derivatives are important chemical materials of effective medicines used for treatment of inflammation. They are of great interest because of their biological properties, such as antipyretic activity (Menozzi et al., 1990), liphoxygenase enzyme inhibition (Brooks et al., 1990) and cholecystokinin (CCK) receptor antagonist activity (Greenwood et al., 1995). We report herein the crystal structure of the title compound, (I).
In the molecule of (I), (Fig. 1), rings A (C4-C9) and C (C13-C18) are, of course, planar. The dihedral angle between them is A/C = 88.94 (3)°. Ring B (N1/N2/C10-C12) has envelope conformation with atom C10 displaced by 0.354 (3) Å from the plane of the other ring atoms. The intramolecular C-H···N hydrogen bonds (Table 1) result in the formation of two planar five-membered rings D (N1/N2/C7/C8/H8A) and E (N1/C10/C13/C14/H14A). They are oriented with respect to the adjacent rings at dihedral angles of A/D = 4.05 (3)° and C/E = 0.50 (3)°. So, they are also nearly coplanar.
In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.