Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036562/hk2301sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036562/hk2301Isup2.hkl |
CCDC reference: 657885
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.076
- wR factor = 0.187
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.746 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.75 e/A PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C18 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H20 N2 O3
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Menozzi et al. (1990); Brooks et al. (1990); Greenwood et al. (1995). For related literatue, see: Zhu et al. (2004). For bond- length data, see: Allen et al. (1987).
To a solution of sodium (40 mmol) in anhydrous methanol (9 ml) was added ethanolamine (4 ml) and n-butanol (20 ml). The methanol was removed by distillation and ethyl 3-(3,4-dimethoxyphenyl)acrylate (9.4 g) was added. The resulting mixture was refluxed for 1 h at 373 K, then 4-methylphenylhydrazine (4.9 g) was added. The reaction mixture was refluxed for a further 6 h, left to cool to room temperature, acidified with acetic acid (36%), allowed to stand, filtered, and the filter cake was crystallized from ethanol to give the title compound (m.p. 412 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (Zhu et al., 2004).
H atoms were positioned geometrically with N—H = 0.86 Å (for NH), C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H atoms, 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.
Pyrazolidin-3-one derivatives 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). In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···N hydrogen bonds (Table 1) cause to the formation of two five-membered planar rings A (N1/C9/C6/C5/H5A) and B (N2/N1/C12/C17/H17A). The five-membered ring C (N1/N2/C9—C11) is not planar and has an envelope conformation with atom C9 is displaced by -0.470 (3) Å from the plane of the other ring atoms. D (C3—C8) and E (C12—C17) rings are, of course, planar and the dihedral angles between the planar rings are A/B = 83.84 (2)°, A/D = 1.65 (3) and B/E = 2.22 (3)°.
In the crystal structure, intermolecular C—H···O and N—H···.O hydrogen bonds (Table 1) link the molecules to form a three-dimensional network (Fig. 2). The intra- and intermolecular hydrogen bonds seem to be effective in the stabilization of the crystal structure.
For general background, see: Menozzi et al. (1990); Brooks et al. (1990); Greenwood et al. (1995). For related literatue, see: Zhu et al. (2004). For bond- length data, see: Allen et al. (1987).
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C18H20N2O3 | Z = 2 |
Mr = 312.36 | F(000) = 332 |
Triclinic, P1 | Dx = 1.248 Mg m−3 |
Hall symbol: -P 1 | Melting point: 412 K |
a = 9.4290 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.107 (2) Å | Cell parameters from 25 reflections |
c = 10.848 (2) Å | θ = 10–13° |
α = 96.50 (3)° | µ = 0.09 mm−1 |
β = 111.60 (3)° | T = 298 K |
γ = 114.43 (3)° | Block, colorless |
V = 831.0 (5) Å3 | 0.40 × 0.30 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 2256 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω/2θ scans | h = −11→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.965, Tmax = 0.982 | l = 0→13 |
3477 measured reflections | 3 standard reflections every 120 min |
3266 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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.05P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3 |
3266 reflections | (Δ/σ)max < 0.001 |
202 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
C18H20N2O3 | γ = 114.43 (3)° |
Mr = 312.36 | V = 831.0 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4290 (19) Å | Mo Kα radiation |
b = 10.107 (2) Å | µ = 0.09 mm−1 |
c = 10.848 (2) Å | T = 298 K |
α = 96.50 (3)° | 0.40 × 0.30 × 0.20 mm |
β = 111.60 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2256 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.033 |
Tmin = 0.965, Tmax = 0.982 | 3 standard reflections every 120 min |
3477 measured reflections | intensity decay: none |
3266 independent reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.54 e Å−3 |
3266 reflections | Δρmin = −0.75 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 > 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 | 0.9140 (3) | 0.7698 (3) | 1.6030 (3) | 0.0823 (10) | |
O2 | 0.6384 (4) | 0.7591 (3) | 1.4264 (3) | 0.0622 (7) | |
O3 | 0.4293 (3) | 0.1296 (3) | 0.9351 (2) | 0.0507 (6) | |
N1 | 0.3685 (3) | 0.0623 (3) | 1.2249 (3) | 0.0408 (6) | |
N2 | 0.4294 (4) | 0.0539 (3) | 1.1247 (3) | 0.0443 (6) | |
H2A | 0.4875 | 0.0072 | 1.1242 | 0.053* | |
C1 | 1.0718 (7) | 0.7904 (6) | 1.6861 (6) | 0.102 | |
H1A | 1.1489 | 0.8963 | 1.7407 | 0.152* | |
H1B | 1.1188 | 0.7605 | 1.6301 | 0.152* | |
H1C | 1.0613 | 0.7290 | 1.7470 | 0.152* | |
C2 | 0.4899 (6) | 0.7622 (4) | 1.3261 (4) | 0.0689 (11) | |
H2B | 0.5106 | 0.8654 | 1.3433 | 0.103* | |
H2C | 0.3871 | 0.6989 | 1.3344 | 0.103* | |
H2D | 0.4729 | 0.7245 | 1.2337 | 0.103* | |
C3 | 0.7828 (5) | 0.6260 (4) | 1.5139 (4) | 0.0520 (9) | |
C4 | 0.7907 (5) | 0.4925 (4) | 1.5148 (4) | 0.0577 (9) | |
H4A | 0.8916 | 0.4962 | 1.5785 | 0.069* | |
C5 | 0.6475 (4) | 0.3518 (4) | 1.4203 (3) | 0.0471 (8) | |
H5A | 0.6528 | 0.2622 | 1.4227 | 0.057* | |
C6 | 0.4998 (4) | 0.3456 (3) | 1.3244 (3) | 0.0375 (7) | |
C7 | 0.4940 (4) | 0.4819 (3) | 1.3249 (3) | 0.0411 (7) | |
H7A | 0.3935 | 0.4783 | 1.2605 | 0.049* | |
C8 | 0.6322 (4) | 0.6205 (3) | 1.4175 (3) | 0.0431 (7) | |
C9 | 0.3381 (4) | 0.1974 (3) | 1.2193 (3) | 0.0397 (7) | |
H9A | 0.2375 | 0.1803 | 1.2359 | 0.048* | |
C10 | 0.3897 (4) | 0.1241 (3) | 1.0309 (3) | 0.0397 (7) | |
C11 | 0.2950 (4) | 0.1966 (3) | 1.0682 (3) | 0.0427 (7) | |
H11A | 0.1697 | 0.1369 | 1.0074 | 0.051* | |
H11B | 0.3374 | 0.2998 | 1.0623 | 0.051* | |
C12 | 0.2129 (4) | −0.0769 (3) | 1.1967 (3) | 0.0391 (7) | |
C13 | 0.1462 (5) | −0.0834 (4) | 1.2907 (4) | 0.0539 (9) | |
H13A | 0.1990 | 0.0017 | 1.3679 | 0.065* | |
C14 | 0.0013 (5) | −0.2156 (4) | 1.2711 (4) | 0.0594 (10) | |
H14A | −0.0435 | −0.2175 | 1.3347 | 0.071* | |
C15 | −0.0788 (4) | −0.3457 (4) | 1.1586 (4) | 0.0502 (8) | |
C16 | −0.0111 (5) | −0.3373 (4) | 1.0668 (4) | 0.0502 (8) | |
H16A | −0.0639 | −0.4225 | 0.9897 | 0.060* | |
C17 | 0.1349 (4) | −0.2051 (4) | 1.0845 (3) | 0.0441 (8) | |
H17A | 0.1794 | −0.2035 | 1.0208 | 0.053* | |
C18 | −0.2397 (5) | −0.4880 (4) | 1.1361 (5) | 0.0746 (12) | |
H18A | −0.2765 | −0.5661 | 1.0541 | 0.112* | |
H18B | −0.3322 | −0.4651 | 1.1242 | 0.112* | |
H18C | −0.2130 | −0.5235 | 1.2157 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0469 (15) | 0.0648 (18) | 0.084 (2) | 0.0143 (13) | 0.0090 (15) | −0.0226 (15) |
O2 | 0.0804 (18) | 0.0322 (12) | 0.0575 (15) | 0.0212 (12) | 0.0256 (14) | 0.0059 (11) |
O3 | 0.0699 (16) | 0.0443 (13) | 0.0469 (13) | 0.0281 (12) | 0.0347 (12) | 0.0180 (11) |
N1 | 0.0494 (15) | 0.0334 (13) | 0.0480 (15) | 0.0201 (12) | 0.0298 (13) | 0.0165 (12) |
N2 | 0.0559 (16) | 0.0431 (15) | 0.0554 (17) | 0.0305 (13) | 0.0366 (14) | 0.0250 (13) |
C1 | 0.102 | 0.102 | 0.102 | 0.050 | 0.047 | 0.032 |
C2 | 0.100 (3) | 0.051 (2) | 0.055 (2) | 0.041 (2) | 0.030 (2) | 0.0209 (18) |
C3 | 0.048 (2) | 0.0449 (19) | 0.0448 (19) | 0.0137 (16) | 0.0198 (16) | −0.0044 (15) |
C4 | 0.046 (2) | 0.063 (2) | 0.049 (2) | 0.0275 (18) | 0.0114 (17) | 0.0023 (17) |
C5 | 0.0481 (19) | 0.0451 (18) | 0.0462 (19) | 0.0231 (16) | 0.0207 (16) | 0.0104 (15) |
C6 | 0.0419 (17) | 0.0340 (15) | 0.0346 (15) | 0.0146 (13) | 0.0209 (14) | 0.0088 (12) |
C7 | 0.0492 (18) | 0.0366 (16) | 0.0369 (16) | 0.0190 (14) | 0.0218 (14) | 0.0110 (13) |
C8 | 0.0530 (19) | 0.0341 (16) | 0.0409 (17) | 0.0168 (14) | 0.0267 (16) | 0.0080 (13) |
C9 | 0.0411 (17) | 0.0307 (15) | 0.0463 (18) | 0.0153 (13) | 0.0219 (14) | 0.0120 (13) |
C10 | 0.0419 (17) | 0.0282 (15) | 0.0408 (17) | 0.0128 (13) | 0.0168 (14) | 0.0086 (13) |
C11 | 0.0457 (18) | 0.0343 (16) | 0.0412 (17) | 0.0197 (14) | 0.0143 (14) | 0.0078 (13) |
C12 | 0.0431 (17) | 0.0319 (15) | 0.0402 (16) | 0.0164 (13) | 0.0185 (14) | 0.0145 (13) |
C13 | 0.065 (2) | 0.0410 (18) | 0.0421 (18) | 0.0117 (17) | 0.0296 (17) | 0.0066 (15) |
C14 | 0.071 (2) | 0.052 (2) | 0.053 (2) | 0.0188 (19) | 0.038 (2) | 0.0196 (17) |
C15 | 0.0482 (19) | 0.0357 (17) | 0.055 (2) | 0.0140 (15) | 0.0187 (17) | 0.0193 (15) |
C16 | 0.054 (2) | 0.0315 (16) | 0.053 (2) | 0.0182 (15) | 0.0186 (17) | 0.0072 (14) |
C17 | 0.0531 (19) | 0.0394 (17) | 0.0467 (18) | 0.0250 (15) | 0.0279 (16) | 0.0104 (14) |
C18 | 0.062 (3) | 0.049 (2) | 0.088 (3) | 0.0066 (19) | 0.033 (2) | 0.026 (2) |
O1—C1 | 1.336 (6) | C6—C9 | 1.521 (4) |
O1—C3 | 1.376 (4) | C7—C8 | 1.370 (4) |
O2—C8 | 1.369 (4) | C7—H7A | 0.9300 |
O2—C2 | 1.438 (5) | C9—C11 | 1.535 (4) |
O3—C10 | 1.226 (4) | C9—H9A | 0.9800 |
N1—N2 | 1.412 (3) | C10—C11 | 1.496 (4) |
N1—C12 | 1.446 (4) | C11—H11A | 0.9700 |
N1—C9 | 1.511 (4) | C11—H11B | 0.9700 |
N2—C10 | 1.335 (4) | C12—C13 | 1.376 (4) |
N2—H2A | 0.8600 | C12—C17 | 1.377 (4) |
C1—H1A | 0.9600 | C13—C14 | 1.382 (5) |
C1—H1B | 0.9600 | C13—H13A | 0.9300 |
C1—H1C | 0.9600 | C14—C15 | 1.387 (5) |
C2—H2B | 0.9600 | C14—H14A | 0.9300 |
C2—H2C | 0.9600 | C15—C16 | 1.360 (5) |
C2—H2D | 0.9600 | C15—C18 | 1.508 (5) |
C3—C4 | 1.383 (5) | C16—C17 | 1.394 (5) |
C3—C8 | 1.393 (5) | C16—H16A | 0.9300 |
C4—C5 | 1.399 (5) | C17—H17A | 0.9300 |
C4—H4A | 0.9300 | C18—H18A | 0.9600 |
C5—C6 | 1.369 (4) | C18—H18B | 0.9600 |
C5—H5A | 0.9300 | C18—H18C | 0.9600 |
C6—C7 | 1.401 (4) | ||
C1—O1—C3 | 119.4 (4) | N1—C9—C11 | 102.6 (2) |
C8—O2—C2 | 117.6 (3) | C6—C9—C11 | 112.0 (2) |
N2—N1—C12 | 113.3 (2) | N1—C9—H9A | 110.2 |
N2—N1—C9 | 103.1 (2) | C6—C9—H9A | 110.2 |
C12—N1—C9 | 112.8 (2) | C11—C9—H9A | 110.2 |
C10—N2—N1 | 114.9 (2) | O3—C10—N2 | 125.2 (3) |
C10—N2—H2A | 122.6 | O3—C10—C11 | 127.6 (3) |
N1—N2—H2A | 122.6 | N2—C10—C11 | 107.2 (3) |
O1—C1—H1A | 109.5 | C10—C11—C9 | 103.3 (3) |
O1—C1—H1B | 109.5 | C10—C11—H11A | 111.1 |
H1A—C1—H1B | 109.5 | C9—C11—H11A | 111.1 |
O1—C1—H1C | 109.5 | C10—C11—H11B | 111.1 |
H1A—C1—H1C | 109.5 | C9—C11—H11B | 111.1 |
H1B—C1—H1C | 109.5 | H11A—C11—H11B | 109.1 |
O2—C2—H2B | 109.5 | C13—C12—C17 | 118.9 (3) |
O2—C2—H2C | 109.5 | C13—C12—N1 | 118.1 (3) |
H2B—C2—H2C | 109.5 | C17—C12—N1 | 122.9 (3) |
O2—C2—H2D | 109.5 | C12—C13—C14 | 120.4 (3) |
H2B—C2—H2D | 109.5 | C12—C13—H13A | 119.8 |
H2C—C2—H2D | 109.5 | C14—C13—H13A | 119.8 |
O1—C3—C4 | 125.3 (3) | C13—C14—C15 | 121.4 (3) |
O1—C3—C8 | 114.9 (3) | C13—C14—H14A | 119.3 |
C4—C3—C8 | 119.8 (3) | C15—C14—H14A | 119.3 |
C3—C4—C5 | 120.3 (3) | C16—C15—C14 | 117.4 (3) |
C3—C4—H4A | 119.8 | C16—C15—C18 | 121.6 (3) |
C5—C4—H4A | 119.8 | C14—C15—C18 | 121.0 (4) |
C6—C5—C4 | 120.2 (3) | C15—C16—C17 | 122.1 (3) |
C6—C5—H5A | 119.9 | C15—C16—H16A | 118.9 |
C4—C5—H5A | 119.9 | C17—C16—H16A | 118.9 |
C5—C6—C7 | 118.7 (3) | C12—C17—C16 | 119.8 (3) |
C5—C6—C9 | 123.5 (3) | C12—C17—H17A | 120.1 |
C7—C6—C9 | 117.8 (3) | C16—C17—H17A | 120.1 |
C8—C7—C6 | 121.8 (3) | C15—C18—H18A | 109.5 |
C8—C7—H7A | 119.1 | C15—C18—H18B | 109.5 |
C6—C7—H7A | 119.1 | H18A—C18—H18B | 109.5 |
O2—C8—C7 | 126.0 (3) | C15—C18—H18C | 109.5 |
O2—C8—C3 | 114.9 (3) | H18A—C18—H18C | 109.5 |
C7—C8—C3 | 119.1 (3) | H18B—C18—H18C | 109.5 |
N1—C9—C6 | 111.6 (3) | ||
C12—N1—N2—C10 | 102.0 (3) | C7—C6—C9—N1 | 176.2 (2) |
C9—N1—N2—C10 | −20.3 (3) | C5—C6—C9—C11 | −120.1 (3) |
C1—O1—C3—C4 | 9.6 (6) | C7—C6—C9—C11 | 61.8 (3) |
C1—O1—C3—C8 | −170.8 (4) | N1—N2—C10—O3 | −179.6 (3) |
O1—C3—C4—C5 | 178.9 (3) | N1—N2—C10—C11 | 2.1 (4) |
C8—C3—C4—C5 | −0.6 (5) | O3—C10—C11—C9 | −161.6 (3) |
C3—C4—C5—C6 | 1.3 (5) | N2—C10—C11—C9 | 16.7 (3) |
C4—C5—C6—C7 | −1.2 (5) | N1—C9—C11—C10 | −27.6 (3) |
C4—C5—C6—C9 | −179.3 (3) | C6—C9—C11—C10 | 92.2 (3) |
C5—C6—C7—C8 | 0.6 (4) | N2—N1—C12—C13 | 177.5 (3) |
C9—C6—C7—C8 | 178.8 (3) | C9—N1—C12—C13 | −65.8 (4) |
C2—O2—C8—C7 | −2.8 (5) | N2—N1—C12—C17 | 1.2 (4) |
C2—O2—C8—C3 | 177.5 (3) | C9—N1—C12—C17 | 117.8 (3) |
C6—C7—C8—O2 | −179.7 (3) | C17—C12—C13—C14 | −1.2 (5) |
C6—C7—C8—C3 | 0.1 (5) | N1—C12—C13—C14 | −177.7 (3) |
O1—C3—C8—O2 | 0.1 (4) | C12—C13—C14—C15 | 1.2 (6) |
C4—C3—C8—O2 | 179.7 (3) | C13—C14—C15—C16 | −1.2 (6) |
O1—C3—C8—C7 | −179.6 (3) | C13—C14—C15—C18 | −178.3 (4) |
C4—C3—C8—C7 | 0.0 (5) | C14—C15—C16—C17 | 1.1 (5) |
N2—N1—C9—C6 | −91.5 (3) | C18—C15—C16—C17 | 178.3 (3) |
C12—N1—C9—C6 | 146.0 (2) | C13—C12—C17—C16 | 1.2 (5) |
N2—N1—C9—C11 | 28.6 (3) | N1—C12—C17—C16 | 177.5 (3) |
C12—N1—C9—C11 | −93.9 (3) | C15—C16—C17—C12 | −1.2 (5) |
C5—C6—C9—N1 | −5.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.00 | 2.836 (5) | 163 |
C1—H1A···O3ii | 0.96 | 2.57 | 3.472 (6) | 156 |
C13—H13A···O2iii | 0.93 | 2.52 | 3.452 (5) | 176 |
C5—H5A···N1 | 0.93 | 2.49 | 2.846 (5) | 103 |
C17—H17A···N2 | 0.93 | 2.43 | 2.755 (5) | 101 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y+1, z+1; (iii) −x+1, −y+1, −z+3. |
Experimental details
Crystal data | |
Chemical formula | C18H20N2O3 |
Mr | 312.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.4290 (19), 10.107 (2), 10.848 (2) |
α, β, γ (°) | 96.50 (3), 111.60 (3), 114.43 (3) |
V (Å3) | 831.0 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.965, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3477, 3266, 2256 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.187, 1.05 |
No. of reflections | 3266 |
No. of parameters | 202 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.75 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.00 | 2.836 (5) | 163.00 |
C1—H1A···O3ii | 0.96 | 2.57 | 3.472 (6) | 156.00 |
C13—H13A···O2iii | 0.93 | 2.52 | 3.452 (5) | 176.00 |
C5—H5A···N1 | 0.93 | 2.49 | 2.846 (5) | 103.00 |
C17—H17A···N2 | 0.93 | 2.43 | 2.755 (5) | 101.00 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y+1, z+1; (iii) −x+1, −y+1, −z+3. |
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Pyrazolidin-3-one derivatives 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). In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···N hydrogen bonds (Table 1) cause to the formation of two five-membered planar rings A (N1/C9/C6/C5/H5A) and B (N2/N1/C12/C17/H17A). The five-membered ring C (N1/N2/C9—C11) is not planar and has an envelope conformation with atom C9 is displaced by -0.470 (3) Å from the plane of the other ring atoms. D (C3—C8) and E (C12—C17) rings are, of course, planar and the dihedral angles between the planar rings are A/B = 83.84 (2)°, A/D = 1.65 (3) and B/E = 2.22 (3)°.
In the crystal structure, intermolecular C—H···O and N—H···.O hydrogen bonds (Table 1) link the molecules to form a three-dimensional network (Fig. 2). The intra- and intermolecular hydrogen bonds seem to be effective in the stabilization of the crystal structure.