Acta Cryst. (2009). E65, o1457 [ doi:10.1107/S1600536809020212 ]
In the title compound, C22H22ClN3O3, the dihedral angles between the planes of the benzene rings and the pyrazole ring are 16.05 (10) and 84.84 (10)°. The conformation of the six-membered heterocyclic ring is close to a screw-boat. The crystal packing is stabilized by weak intermolecular C-H
O interactions and is also consolidated by C-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions.
A solution containing ethyl-3-(4-chlorophenyl)-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate (146 mg, 0.4 mmol), 2-(3,4-dimethoxyphenyl)ethanamine (724 mg, 4.0 mmol) and potassium iodide (13 mg, 0.08 mmol) in acetonitrile (10 ml) was refluxed under nitrogen for 3 h. Then the mixture was cooled, filtered, and the solvent was removed under reduced pressure. The product was obtained in 57% yield by column chromatography on silica gel using ethyl acetate as eluent. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate at room temperature for 5 days.
The H atoms were located in difference Fourier maps, their positional and isotropic vibrational parameters were refined freely except for the methyl H-atoms which were included in the refinements at geometrically idealized positions in riding mode with C–H = 0.96 Å and Uiso(H) = 1.5 Ueq(C).
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./pv2160fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at 30% probability level. |
| C22H22ClN3O3 | Z = 2 |
| Mr = 411.88 | F(000) = 432 |
| Triclinic, P1 | Dx = 1.386 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.1709 (4) Å | Cell parameters from 2906 reflections |
| b = 10.6982 (5) Å | θ = 3.0–26.1° |
| c = 13.9169 (6) Å | µ = 0.22 mm−1 |
| α = 81.156 (3)° | T = 293 K |
| β = 77.150 (2)° | Block, colorless |
| γ = 72.278 (2)° | 0.40 × 0.20 × 0.10 mm |
| V = 987.25 (8) Å3 |
| Bruker SMART CCD area-detector diffractometer | 3999 independent reflections |
| Radiation source: fine-focus sealed tube | 2969 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| φ and ω scans | θmax = 26.4°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Bruker 2005) | h = −7→8 |
| Tmin = 0.916, Tmax = 0.978 | k = −13→13 |
| 8654 measured reflections | l = −17→17 |
| 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1941P] where P = (Fo2 + 2Fc2)/3 |
| 3999 reflections | (Δ/σ)max < 0.001 |
| 326 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.30 e Å−3 |
| C22H22ClN3O3 | γ = 72.278 (2)° |
| Mr = 411.88 | V = 987.25 (8) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.1709 (4) Å | Mo Kα radiation |
| b = 10.6982 (5) Å | µ = 0.22 mm−1 |
| c = 13.9169 (6) Å | T = 293 K |
| α = 81.156 (3)° | 0.40 × 0.20 × 0.10 mm |
| β = 77.150 (2)° |
| Bruker SMART CCD area-detector diffractometer | 3999 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker 2005) | 2969 reflections with I > 2σ(I) |
| Tmin = 0.916, Tmax = 0.978 | Rint = 0.021 |
| 8654 measured reflections | θmax = 26.4° |
| R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.115 | Δρmax = 0.20 e Å−3 |
| S = 1.03 | Δρmin = −0.30 e Å−3 |
| 3999 reflections | Absolute structure: ? |
| 326 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Cl | 0.20421 (8) | 0.95549 (6) | 0.40014 (4) | 0.06084 (19) | |
| N1 | −0.4397 (2) | 0.70036 (14) | 0.26041 (11) | 0.0390 (4) | |
| N2 | −0.5553 (2) | 0.69103 (14) | 0.19947 (10) | 0.0367 (4) | |
| N3 | −0.7921 (2) | 0.70588 (15) | 0.06451 (11) | 0.0390 (4) | |
| O1 | −0.7274 (2) | 0.89705 (14) | −0.00841 (10) | 0.0575 (4) | |
| O2 | −1.3542 (2) | 0.72159 (14) | −0.37111 (10) | 0.0533 (4) | |
| O3 | −0.9862 (2) | 0.58773 (15) | −0.41075 (10) | 0.0544 (4) | |
| C1 | 0.0314 (3) | 0.91488 (18) | 0.34943 (14) | 0.0406 (4) | |
| C2 | −0.0785 (3) | 0.8341 (2) | 0.40461 (15) | 0.0450 (5) | |
| H2 | −0.065 (3) | 0.8025 (19) | 0.4699 (15) | 0.048 (6)* | |
| C3 | −0.2109 (3) | 0.79940 (19) | 0.36251 (14) | 0.0419 (4) | |
| H3 | −0.289 (3) | 0.744 (2) | 0.3994 (15) | 0.057 (6)* | |
| C4 | −0.2335 (3) | 0.84383 (17) | 0.26496 (12) | 0.0343 (4) | |
| C5 | −0.1236 (3) | 0.92790 (18) | 0.21187 (14) | 0.0390 (4) | |
| H5 | −0.135 (3) | 0.9556 (19) | 0.1468 (15) | 0.046 (5)* | |
| C6 | 0.0084 (3) | 0.96339 (19) | 0.25367 (14) | 0.0411 (4) | |
| H6 | 0.082 (3) | 1.019 (2) | 0.2150 (15) | 0.049 (6)* | |
| C7 | −0.3707 (3) | 0.80384 (17) | 0.21908 (12) | 0.0345 (4) | |
| C8 | −0.4449 (3) | 0.86047 (19) | 0.13250 (13) | 0.0367 (4) | |
| H8 | −0.421 (3) | 0.933 (2) | 0.0897 (15) | 0.047 (6)* | |
| C9 | −0.5643 (3) | 0.78601 (17) | 0.12271 (12) | 0.0344 (4) | |
| C10 | −0.6987 (3) | 0.80106 (19) | 0.05288 (13) | 0.0386 (4) | |
| C11 | −0.7288 (4) | 0.5823 (2) | 0.12678 (16) | 0.0499 (5) | |
| H11B | −0.842 (3) | 0.543 (2) | 0.1422 (16) | 0.058 (6)* | |
| H11A | −0.600 (4) | 0.519 (2) | 0.0875 (17) | 0.066 (7)* | |
| C12 | −0.6833 (4) | 0.6042 (2) | 0.22192 (15) | 0.0462 (5) | |
| H12B | −0.611 (3) | 0.522 (2) | 0.2536 (15) | 0.053 (6)* | |
| H12A | −0.811 (4) | 0.647 (2) | 0.2650 (17) | 0.069 (7)* | |
| C13 | −0.9414 (3) | 0.7191 (2) | 0.00409 (15) | 0.0424 (5) | |
| H13B | −1.051 (3) | 0.684 (2) | 0.0467 (15) | 0.052 (6)* | |
| C14 | −0.8546 (3) | 0.6485 (3) | −0.08922 (16) | 0.0488 (5) | |
| H14B | −0.807 (4) | 0.551 (3) | −0.0693 (18) | 0.073 (7)* | |
| H14A | −0.736 (4) | 0.676 (2) | −0.1225 (17) | 0.066 (7)* | |
| C15 | −0.9982 (3) | 0.67175 (18) | −0.16026 (13) | 0.0383 (4) | |
| C16 | −1.1963 (3) | 0.7426 (2) | −0.13969 (14) | 0.0416 (4) | |
| H16 | −1.255 (3) | 0.777 (2) | −0.0773 (16) | 0.056 (6)* | |
| C17 | −1.3206 (3) | 0.7617 (2) | −0.20844 (15) | 0.0429 (5) | |
| H17 | −1.458 (3) | 0.814 (2) | −0.1909 (14) | 0.047 (6)* | |
| C18 | −1.2466 (3) | 0.70993 (17) | −0.29847 (14) | 0.0392 (4) | |
| C19 | −1.0451 (3) | 0.63712 (18) | −0.32041 (13) | 0.0387 (4) | |
| C20 | −0.9246 (3) | 0.61940 (19) | −0.25182 (14) | 0.0399 (4) | |
| H20 | −0.793 (4) | 0.570 (2) | −0.2684 (15) | 0.056 (6)* | |
| C21 | −1.5441 (3) | 0.8157 (2) | −0.36227 (18) | 0.0613 (6) | |
| H21A | −1.6042 | 0.8145 | −0.4172 | 0.092* | |
| H21B | −1.5293 | 0.9018 | −0.3621 | 0.092* | |
| H21C | −1.6275 | 0.7944 | −0.3016 | 0.092* | |
| C22 | −0.7782 (3) | 0.5470 (2) | −0.45031 (16) | 0.0593 (6) | |
| H22A | −0.7578 | 0.5147 | −0.5136 | 0.089* | |
| H22B | −0.7124 | 0.4782 | −0.4060 | 0.089* | |
| H22C | −0.7243 | 0.6205 | −0.4579 | 0.089* | |
| H13A | −0.998 (3) | 0.813 (2) | −0.0122 (14) | 0.048 (6)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl | 0.0547 (4) | 0.0822 (4) | 0.0621 (4) | −0.0307 (3) | −0.0219 (3) | −0.0163 (3) |
| N1 | 0.0449 (9) | 0.0398 (8) | 0.0395 (8) | −0.0162 (7) | −0.0192 (7) | 0.0006 (7) |
| N2 | 0.0410 (9) | 0.0385 (8) | 0.0365 (8) | −0.0167 (7) | −0.0151 (7) | 0.0016 (6) |
| N3 | 0.0417 (9) | 0.0462 (9) | 0.0368 (8) | −0.0195 (7) | −0.0158 (7) | −0.0003 (7) |
| O1 | 0.0699 (10) | 0.0651 (9) | 0.0521 (8) | −0.0378 (8) | −0.0347 (8) | 0.0235 (7) |
| O2 | 0.0527 (9) | 0.0580 (9) | 0.0527 (8) | −0.0050 (7) | −0.0288 (7) | −0.0097 (7) |
| O3 | 0.0521 (9) | 0.0692 (10) | 0.0418 (8) | −0.0064 (8) | −0.0151 (7) | −0.0174 (7) |
| C1 | 0.0382 (11) | 0.0423 (10) | 0.0462 (11) | −0.0098 (9) | −0.0149 (8) | −0.0116 (8) |
| C2 | 0.0546 (13) | 0.0505 (11) | 0.0368 (10) | −0.0187 (10) | −0.0192 (9) | −0.0009 (9) |
| C3 | 0.0489 (12) | 0.0426 (11) | 0.0398 (10) | −0.0193 (10) | −0.0133 (9) | 0.0003 (8) |
| C4 | 0.0354 (10) | 0.0353 (9) | 0.0345 (9) | −0.0091 (8) | −0.0114 (8) | −0.0043 (7) |
| C5 | 0.0416 (11) | 0.0415 (10) | 0.0356 (10) | −0.0121 (9) | −0.0123 (8) | −0.0002 (8) |
| C6 | 0.0412 (11) | 0.0422 (11) | 0.0442 (11) | −0.0172 (9) | −0.0086 (9) | −0.0045 (8) |
| C7 | 0.0352 (10) | 0.0355 (9) | 0.0344 (9) | −0.0103 (8) | −0.0088 (8) | −0.0040 (7) |
| C8 | 0.0384 (10) | 0.0402 (10) | 0.0357 (9) | −0.0168 (9) | −0.0116 (8) | 0.0021 (8) |
| C9 | 0.0353 (10) | 0.0379 (9) | 0.0319 (9) | −0.0126 (8) | −0.0093 (7) | 0.0001 (7) |
| C10 | 0.0391 (11) | 0.0468 (11) | 0.0344 (10) | −0.0174 (9) | −0.0104 (8) | −0.0007 (8) |
| C11 | 0.0605 (15) | 0.0477 (12) | 0.0535 (12) | −0.0270 (12) | −0.0243 (11) | 0.0039 (10) |
| C12 | 0.0566 (14) | 0.0456 (12) | 0.0471 (12) | −0.0281 (11) | −0.0209 (11) | 0.0083 (10) |
| C13 | 0.0391 (11) | 0.0545 (13) | 0.0415 (11) | −0.0187 (10) | −0.0145 (9) | −0.0061 (9) |
| C14 | 0.0400 (12) | 0.0676 (15) | 0.0436 (11) | −0.0146 (11) | −0.0127 (9) | −0.0133 (10) |
| C15 | 0.0396 (11) | 0.0434 (10) | 0.0385 (10) | −0.0179 (9) | −0.0109 (8) | −0.0055 (8) |
| C16 | 0.0408 (11) | 0.0498 (11) | 0.0392 (10) | −0.0164 (9) | −0.0083 (9) | −0.0109 (9) |
| C17 | 0.0360 (11) | 0.0456 (11) | 0.0495 (11) | −0.0111 (9) | −0.0101 (9) | −0.0089 (9) |
| C18 | 0.0442 (11) | 0.0368 (10) | 0.0434 (10) | −0.0155 (9) | −0.0189 (9) | 0.0003 (8) |
| C19 | 0.0448 (11) | 0.0401 (10) | 0.0346 (9) | −0.0140 (9) | −0.0116 (8) | −0.0029 (8) |
| C20 | 0.0374 (11) | 0.0433 (11) | 0.0407 (10) | −0.0108 (9) | −0.0102 (9) | −0.0060 (8) |
| C21 | 0.0494 (13) | 0.0657 (15) | 0.0729 (15) | −0.0083 (12) | −0.0315 (12) | −0.0051 (12) |
| C22 | 0.0617 (16) | 0.0631 (14) | 0.0478 (12) | −0.0061 (12) | −0.0090 (11) | −0.0142 (10) |
| Cl—C1 | 1.7416 (18) | C9—C10 | 1.474 (2) |
| N1—N2 | 1.3439 (19) | C11—C12 | 1.499 (3) |
| N1—C7 | 1.346 (2) | C11—H11B | 0.99 (2) |
| N2—C9 | 1.355 (2) | C11—H11A | 1.06 (2) |
| N2—C12 | 1.452 (2) | C12—H12B | 0.97 (2) |
| N3—C10 | 1.352 (2) | C12—H12A | 1.00 (3) |
| N3—C13 | 1.465 (2) | C13—C14 | 1.516 (3) |
| N3—C11 | 1.470 (2) | C13—H13B | 1.01 (2) |
| O1—C10 | 1.227 (2) | C13—H13A | 0.97 (2) |
| O2—C18 | 1.372 (2) | C14—C15 | 1.523 (2) |
| O2—C21 | 1.418 (3) | C14—H14B | 1.01 (3) |
| O3—C19 | 1.368 (2) | C14—H14A | 0.98 (2) |
| O3—C22 | 1.425 (3) | C15—C16 | 1.380 (3) |
| C1—C2 | 1.378 (3) | C15—C20 | 1.399 (3) |
| C1—C6 | 1.380 (3) | C16—C17 | 1.401 (3) |
| C2—C3 | 1.383 (3) | C16—H16 | 0.95 (2) |
| C2—H2 | 0.94 (2) | C17—C18 | 1.377 (3) |
| C3—C4 | 1.396 (2) | C17—H17 | 0.97 (2) |
| C3—H3 | 0.95 (2) | C18—C19 | 1.407 (3) |
| C4—C5 | 1.394 (3) | C19—C20 | 1.380 (2) |
| C4—C7 | 1.476 (2) | C20—H20 | 0.93 (2) |
| C5—C6 | 1.382 (3) | C21—H21A | 0.9600 |
| C5—H5 | 0.92 (2) | C21—H21B | 0.9600 |
| C6—H6 | 0.95 (2) | C21—H21C | 0.9600 |
| C7—C8 | 1.402 (2) | C22—H22A | 0.9600 |
| C8—C9 | 1.374 (2) | C22—H22B | 0.9600 |
| C8—H8 | 0.94 (2) | C22—H22C | 0.9600 |
| N2—N1—C7 | 104.41 (13) | C11—C12—H12B | 110.9 (12) |
| N1—N2—C9 | 112.51 (14) | N2—C12—H12A | 109.6 (14) |
| N1—N2—C12 | 123.74 (14) | C11—C12—H12A | 108.3 (13) |
| C9—N2—C12 | 122.94 (15) | H12B—C12—H12A | 112.2 (19) |
| C10—N3—C13 | 119.09 (15) | N3—C13—C14 | 112.60 (17) |
| C10—N3—C11 | 121.19 (15) | N3—C13—H13B | 107.6 (12) |
| C13—N3—C11 | 119.25 (15) | C14—C13—H13B | 111.3 (12) |
| C18—O2—C21 | 117.38 (16) | N3—C13—H13A | 107.0 (12) |
| C19—O3—C22 | 118.05 (15) | C14—C13—H13A | 110.7 (12) |
| C2—C1—C6 | 120.98 (17) | H13B—C13—H13A | 107.4 (17) |
| C2—C1—Cl | 119.85 (14) | C13—C14—C15 | 114.67 (18) |
| C6—C1—Cl | 119.16 (15) | C13—C14—H14B | 108.3 (14) |
| C1—C2—C3 | 119.31 (18) | C15—C14—H14B | 109.1 (14) |
| C1—C2—H2 | 121.1 (13) | C13—C14—H14A | 108.0 (14) |
| C3—C2—H2 | 119.6 (13) | C15—C14—H14A | 110.3 (13) |
| C2—C3—C4 | 121.06 (19) | H14B—C14—H14A | 106 (2) |
| C2—C3—H3 | 120.8 (13) | C16—C15—C20 | 118.18 (17) |
| C4—C3—H3 | 118.2 (13) | C16—C15—C14 | 123.66 (17) |
| C5—C4—C3 | 118.22 (16) | C20—C15—C14 | 118.15 (17) |
| C5—C4—C7 | 120.68 (15) | C15—C16—C17 | 121.03 (18) |
| C3—C4—C7 | 121.10 (16) | C15—C16—H16 | 121.5 (13) |
| C6—C5—C4 | 120.96 (17) | C17—C16—H16 | 117.4 (13) |
| C6—C5—H5 | 120.4 (12) | C18—C17—C16 | 120.32 (19) |
| C4—C5—H5 | 118.6 (12) | C18—C17—H17 | 122.1 (12) |
| C1—C6—C5 | 119.42 (18) | C16—C17—H17 | 117.5 (12) |
| C1—C6—H6 | 121.9 (12) | O2—C18—C17 | 125.43 (18) |
| C5—C6—H6 | 118.7 (12) | O2—C18—C19 | 115.24 (16) |
| N1—C7—C8 | 111.40 (15) | C17—C18—C19 | 119.32 (17) |
| N1—C7—C4 | 120.36 (15) | O3—C19—C20 | 125.34 (18) |
| C8—C7—C4 | 128.23 (16) | O3—C19—C18 | 115.07 (15) |
| C9—C8—C7 | 104.71 (16) | C20—C19—C18 | 119.59 (17) |
| C9—C8—H8 | 126.3 (12) | C19—C20—C15 | 121.57 (19) |
| C7—C8—H8 | 129.0 (12) | C19—C20—H20 | 117.2 (13) |
| N2—C9—C8 | 106.96 (15) | C15—C20—H20 | 121.2 (13) |
| N2—C9—C10 | 120.98 (15) | O2—C21—H21A | 109.5 |
| C8—C9—C10 | 131.84 (16) | O2—C21—H21B | 109.5 |
| O1—C10—N3 | 123.38 (16) | H21A—C21—H21B | 109.5 |
| O1—C10—C9 | 121.11 (16) | O2—C21—H21C | 109.5 |
| N3—C10—C9 | 115.44 (15) | H21A—C21—H21C | 109.5 |
| N3—C11—C12 | 112.58 (17) | H21B—C21—H21C | 109.5 |
| N3—C11—H11B | 106.1 (12) | O3—C22—H22A | 109.5 |
| C12—C11—H11B | 108.8 (12) | O3—C22—H22B | 109.5 |
| N3—C11—H11A | 109.6 (12) | H22A—C22—H22B | 109.5 |
| C12—C11—H11A | 108.6 (12) | O3—C22—H22C | 109.5 |
| H11B—C11—H11A | 111.2 (18) | H22A—C22—H22C | 109.5 |
| N2—C12—C11 | 108.36 (16) | H22B—C22—H22C | 109.5 |
| N2—C12—H12B | 107.4 (13) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O1i | 0.92 (2) | 2.48 (2) | 3.341 (2) | 156.3 (17) |
| C8—H8···O1i | 0.94 (2) | 2.39 (2) | 3.296 (2) | 161.4 (19) |
| C11—H11B···Cg1ii | 0.99 (2) | 2.67 (2) | 3.413 (2) | 132.2 (16) |
| C12—H12A···Cg2iii | 1.00 (3) | 2.77 (2) | 3.640 (2) | 146.2 (17) |
| C21—H21B···Cg2iv | 0.96 | 2.98 | 3.531 (2) | 117 |
| Symmetry codes: (i) −x−1, −y+2, −z; (ii) −x−2, −y+1, −z; (iii) x−1, y, z; (iv) −x−2, −y+2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O1i | 0.92 (2) | 2.48 (2) | 3.341 (2) | 156.3 (17) |
| C8—H8···O1i | 0.94 (2) | 2.39 (2) | 3.296 (2) | 161.4 (19) |
| C11—H11B···Cg1ii | 0.99 (2) | 2.67 (2) | 3.413 (2) | 132.2 (16) |
| C12—H12A···Cg2iii | 1.00 (3) | 2.77 (2) | 3.640 (2) | 146.2 (17) |
| C21—H21B···Cg2iv | 0.96 | 2.98 | 3.531 (2) | 117 |
| Symmetry codes: (i) −x−1, −y+2, −z; (ii) −x−2, −y+1, −z; (iii) x−1, y, z; (iv) −x−2, −y+2, −z. |
This study was supported by the Science and Technology Developmental Project of Shandong Province (2008 GG10002034).
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Many pyrazole derivatives are known to exhibit a wide range of biological properties (Farag et al., 2008; Szabó et al., 2008). As part of our continuing project on the study of the interactions occurring between small molecules and proteins (Pan et al., 2008; Xie et al., 2008; Zhang et al., 2008), we report here the crystal structure of the title compound.
The molecular structure of the title compound is illustrated in Fig. 1. In contrast to our previously reported structure of a related compound (Zhang et al., 2008), the conformation of the six-membered heterocyclic ring (N2/N3/C9—C12) in the title compound is close to a screw-boat, with atoms C11 and N3 out of the plane of the remaining four atoms by 0.681 (2) and 0.214 (2) Å, respectively. In the crystal structure, the dihedral angles of the phenyl rings (C1—C6) and (C15—C20) with the pyrazol ring (N1/N2/C7—C9) are 16.05 (10) and 84.84 (10)°, respectively. The crystal packing is stabilized by intermolecular C—H···O interactions and is further consolidated by C—H···π interactions (Table 1).