Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037993/hb2502sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037993/hb2502Isup2.hkl |
CCDC reference: 660223
A mixture of 1-phenyl-3-methyl-4-benzoyl-pyrazolone-5 (1 mmol) and 4-trifluoromethylaniline (1 mmol) in anhydrous ethanol (30 ml) was refluxed for 3 hr, and then cooled to room temperature. The precipitate was filtered and dried. The crude product was recrystallized from ethanol. Yellow crystals were thus obtained in 83% yield. A single-crystal of (I) suitable for an X-ray structural analysis was obtained by slowly evaporating a ethanolic solution at room temperature.
All H atoms were initially located in a difference map then relocated to idealized locations (C—H = 0.93–0.96 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The highest difference peak is 1.33 Å from F2.
The title compound, (I), was synthesized as part of a continuing project involving the structures of pyrazolone derivatives. Pyrazolone derivatives are well known for their potential applications in the areas of pharmaceuticals, agrochemicals, dyes, and pigments, and also as chelating agents and extracting agents. Moreover, they are capable of prototropic tautomerism (Akama & Tong, 1996; Eller & Holzer, 2004).
The molecule of (I) exists in enamine-keto tautomeric form in the crystal instead of the imine form (Fig. 1), as in 4-[(Z)-(benzylamino) phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one (Jiang et al., 2004). The central pyrazolone (C1–C3/N1/N2) ring is essentially planar, with an r.m.s. deviation of 0.0116 Å for the fitted atoms. This ring makes dihedral angles of 31.8 (2), 45.4 (2) and 71.2 (2)° with the C5–C10, C12–C17 and C19–C24 phenyl rings, respectively. Similar tautomerism has also been observed in related pyrazolone analogues reported by us previously (Sun et al., 2006, 2007). In addition, the present compound also features an intramolecular hydrogen bond between the N3 and O1 atoms (Table 1), leading to the fact that atoms O1 and N3 are on the same side of the C2–C11 bond, which will be the potential bidentate N,O-chelate positions after deprotonation to form functional complexes as candidates with catalytic applications (Lu et al., 2006).
For related structures, see: Sun et al. (2006, 2007). For background literature, see: Akama & Tong (1996); Eller & Holzer (2004); Jiang et al. (2004); Lu et al.(2006).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. View of the molecular structure of (I) showing displacement ellipsoids at the 50% probability level. H atoms are shown as spheres of arbitrary radius. The dashed line indicates hydrogen bond. |
C24H18F3N3O | Z = 2 |
Mr = 421.41 | F(000) = 436 |
Triclinic, P1 | Dx = 1.382 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6059 (9) Å | Cell parameters from 3675 reflections |
b = 10.9913 (12) Å | θ = 2.1–28.2° |
c = 13.8057 (15) Å | µ = 0.11 mm−1 |
α = 108.448 (2)° | T = 273 K |
β = 100.227 (2)° | Block, yellow |
γ = 105.178 (2)° | 0.35 × 0.26 × 0.18 mm |
V = 1013.0 (2) Å3 |
Bruker SMART CCD diffractometer | 3527 independent reflections |
Radiation source: fine-focus sealed tube | 3079 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.964, Tmax = 0.981 | k = −12→13 |
5150 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.088P)2 + 0.5882P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3527 reflections | Δρmax = 0.71 e Å−3 |
282 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (5) |
C24H18F3N3O | γ = 105.178 (2)° |
Mr = 421.41 | V = 1013.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6059 (9) Å | Mo Kα radiation |
b = 10.9913 (12) Å | µ = 0.11 mm−1 |
c = 13.8057 (15) Å | T = 273 K |
α = 108.448 (2)° | 0.35 × 0.26 × 0.18 mm |
β = 100.227 (2)° |
Bruker SMART CCD diffractometer | 3527 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3079 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.981 | Rint = 0.011 |
5150 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.71 e Å−3 |
3527 reflections | Δρmin = −0.40 e Å−3 |
282 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 | ||
F1 | 1.2873 (3) | 0.7703 (4) | 0.52098 (18) | 0.1651 (15) | |
F2 | 1.1537 (3) | 0.7329 (3) | 0.6340 (3) | 0.1570 (13) | |
F3 | 1.2712 (3) | 0.9287 (2) | 0.64567 (18) | 0.1190 (8) | |
O1 | 0.2518 (2) | 0.89023 (15) | 0.26159 (13) | 0.0553 (4) | |
N1 | −0.0459 (2) | 0.74140 (17) | 0.14646 (14) | 0.0452 (4) | |
N2 | −0.1474 (3) | 0.60170 (17) | 0.10526 (14) | 0.0481 (5) | |
N3 | 0.4577 (2) | 0.74680 (18) | 0.32255 (14) | 0.0489 (5) | |
H3 | 0.4386 | 0.8219 | 0.3269 | 0.059* | |
C1 | 0.1347 (3) | 0.7735 (2) | 0.20940 (17) | 0.0433 (5) | |
C2 | 0.1515 (3) | 0.6428 (2) | 0.20245 (16) | 0.0418 (5) | |
C3 | −0.0321 (3) | 0.5436 (2) | 0.13746 (17) | 0.0445 (5) | |
C4 | −0.1047 (4) | 0.3929 (2) | 0.1069 (2) | 0.0617 (7) | |
H4A | −0.2385 | 0.3579 | 0.0713 | 0.093* | |
H4B | −0.0832 | 0.3724 | 0.1697 | 0.093* | |
H4C | −0.0393 | 0.3514 | 0.0599 | 0.093* | |
C5 | −0.1398 (3) | 0.8326 (2) | 0.13113 (16) | 0.0446 (5) | |
C6 | −0.3329 (3) | 0.7998 (3) | 0.11965 (19) | 0.0545 (6) | |
H6 | −0.4027 | 0.7169 | 0.1203 | 0.065* | |
C7 | −0.4214 (4) | 0.8914 (3) | 0.1072 (2) | 0.0634 (7) | |
H7 | −0.5509 | 0.8701 | 0.0998 | 0.076* | |
C8 | −0.3185 (4) | 1.0139 (3) | 0.1055 (2) | 0.0668 (7) | |
H8 | −0.3780 | 1.0756 | 0.0978 | 0.080* | |
C9 | −0.1283 (4) | 1.0441 (3) | 0.1152 (2) | 0.0692 (7) | |
H9 | −0.0592 | 1.1263 | 0.1133 | 0.083* | |
C10 | −0.0376 (4) | 0.9544 (2) | 0.1279 (2) | 0.0583 (6) | |
H10 | 0.0917 | 0.9759 | 0.1342 | 0.070* | |
C11 | 0.3135 (3) | 0.6321 (2) | 0.25890 (16) | 0.0418 (5) | |
C12 | 0.6381 (3) | 0.7604 (2) | 0.38376 (17) | 0.0454 (5) | |
C13 | 0.7166 (3) | 0.8622 (2) | 0.48522 (18) | 0.0504 (5) | |
H13 | 0.6512 | 0.9199 | 0.5115 | 0.061* | |
C14 | 0.8908 (3) | 0.8778 (2) | 0.54689 (18) | 0.0551 (6) | |
H14 | 0.9428 | 0.9462 | 0.6147 | 0.066* | |
C15 | 0.9884 (3) | 0.7923 (3) | 0.50833 (18) | 0.0523 (6) | |
C16 | 0.9117 (3) | 0.6922 (3) | 0.40642 (18) | 0.0566 (6) | |
H16 | 0.9775 | 0.6347 | 0.3802 | 0.068* | |
C17 | 0.7391 (3) | 0.6772 (3) | 0.34380 (18) | 0.0552 (6) | |
H17 | 0.6902 | 0.6115 | 0.2748 | 0.066* | |
C18 | 1.1727 (4) | 0.8038 (3) | 0.5758 (2) | 0.0710 (8) | |
C19 | 0.3297 (3) | 0.4991 (2) | 0.25615 (16) | 0.0433 (5) | |
C20 | 0.3411 (3) | 0.4054 (2) | 0.16447 (18) | 0.0525 (6) | |
H20 | 0.3318 | 0.4228 | 0.1024 | 0.063* | |
C21 | 0.3666 (4) | 0.2856 (2) | 0.1664 (2) | 0.0650 (7) | |
H21 | 0.3753 | 0.2228 | 0.1054 | 0.078* | |
C22 | 0.3792 (4) | 0.2590 (3) | 0.2577 (2) | 0.0694 (8) | |
H22 | 0.3982 | 0.1791 | 0.2586 | 0.083* | |
C23 | 0.3637 (4) | 0.3507 (3) | 0.3479 (2) | 0.0670 (7) | |
H23 | 0.3692 | 0.3317 | 0.4091 | 0.080* | |
C24 | 0.3399 (3) | 0.4708 (2) | 0.34747 (19) | 0.0540 (6) | |
H24 | 0.3307 | 0.5329 | 0.4086 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0721 (13) | 0.299 (4) | 0.0878 (15) | 0.0989 (19) | 0.0070 (11) | 0.0061 (19) |
F2 | 0.0921 (16) | 0.199 (3) | 0.202 (3) | 0.0332 (17) | −0.0128 (16) | 0.148 (3) |
F3 | 0.0832 (13) | 0.1226 (17) | 0.0949 (14) | 0.0156 (12) | −0.0288 (11) | 0.0146 (13) |
O1 | 0.0488 (9) | 0.0386 (8) | 0.0681 (10) | 0.0136 (7) | 0.0022 (7) | 0.0158 (7) |
N1 | 0.0427 (9) | 0.0382 (9) | 0.0524 (10) | 0.0155 (7) | 0.0047 (8) | 0.0179 (8) |
N2 | 0.0468 (10) | 0.0396 (9) | 0.0520 (10) | 0.0136 (8) | 0.0049 (8) | 0.0159 (8) |
N3 | 0.0460 (10) | 0.0439 (10) | 0.0538 (11) | 0.0185 (8) | 0.0044 (8) | 0.0175 (8) |
C1 | 0.0419 (11) | 0.0416 (11) | 0.0464 (11) | 0.0161 (9) | 0.0095 (9) | 0.0170 (9) |
C2 | 0.0450 (11) | 0.0394 (10) | 0.0426 (10) | 0.0177 (9) | 0.0102 (9) | 0.0161 (8) |
C3 | 0.0460 (11) | 0.0412 (11) | 0.0455 (11) | 0.0162 (9) | 0.0088 (9) | 0.0167 (9) |
C4 | 0.0560 (14) | 0.0396 (12) | 0.0779 (17) | 0.0128 (10) | 0.0039 (12) | 0.0184 (11) |
C5 | 0.0494 (12) | 0.0447 (11) | 0.0410 (11) | 0.0221 (9) | 0.0074 (9) | 0.0163 (9) |
C6 | 0.0501 (13) | 0.0626 (14) | 0.0567 (13) | 0.0241 (11) | 0.0124 (10) | 0.0277 (11) |
C7 | 0.0550 (14) | 0.0838 (18) | 0.0582 (14) | 0.0401 (14) | 0.0110 (11) | 0.0251 (13) |
C8 | 0.0799 (18) | 0.0612 (15) | 0.0594 (15) | 0.0437 (14) | 0.0031 (13) | 0.0162 (12) |
C9 | 0.0738 (17) | 0.0480 (13) | 0.0828 (18) | 0.0259 (12) | 0.0036 (14) | 0.0273 (13) |
C10 | 0.0531 (13) | 0.0477 (13) | 0.0747 (16) | 0.0195 (10) | 0.0091 (11) | 0.0273 (12) |
C11 | 0.0463 (11) | 0.0435 (11) | 0.0386 (10) | 0.0189 (9) | 0.0130 (9) | 0.0162 (8) |
C12 | 0.0420 (11) | 0.0480 (11) | 0.0476 (11) | 0.0156 (9) | 0.0101 (9) | 0.0215 (9) |
C13 | 0.0486 (12) | 0.0439 (11) | 0.0547 (13) | 0.0155 (9) | 0.0128 (10) | 0.0147 (10) |
C14 | 0.0493 (12) | 0.0561 (13) | 0.0465 (12) | 0.0113 (10) | 0.0078 (10) | 0.0111 (10) |
C15 | 0.0418 (11) | 0.0667 (14) | 0.0468 (12) | 0.0154 (10) | 0.0123 (9) | 0.0220 (11) |
C16 | 0.0479 (12) | 0.0717 (16) | 0.0513 (13) | 0.0291 (11) | 0.0153 (10) | 0.0172 (11) |
C17 | 0.0477 (12) | 0.0669 (15) | 0.0427 (11) | 0.0225 (11) | 0.0092 (9) | 0.0099 (10) |
C18 | 0.0534 (15) | 0.095 (2) | 0.0564 (15) | 0.0266 (14) | 0.0080 (12) | 0.0216 (15) |
C19 | 0.0410 (11) | 0.0446 (11) | 0.0462 (11) | 0.0188 (9) | 0.0080 (8) | 0.0188 (9) |
C20 | 0.0580 (13) | 0.0514 (13) | 0.0474 (12) | 0.0253 (11) | 0.0082 (10) | 0.0162 (10) |
C21 | 0.0654 (15) | 0.0501 (13) | 0.0686 (16) | 0.0292 (12) | 0.0031 (12) | 0.0096 (12) |
C22 | 0.0652 (16) | 0.0463 (13) | 0.087 (2) | 0.0205 (12) | −0.0063 (14) | 0.0266 (13) |
C23 | 0.0690 (16) | 0.0641 (16) | 0.0682 (16) | 0.0160 (13) | 0.0025 (13) | 0.0403 (14) |
C24 | 0.0594 (14) | 0.0561 (13) | 0.0494 (12) | 0.0209 (11) | 0.0129 (10) | 0.0243 (10) |
F1—C18 | 1.301 (3) | C9—C10 | 1.379 (3) |
F2—C18 | 1.286 (4) | C9—H9 | 0.9300 |
F3—C18 | 1.321 (4) | C10—H10 | 0.9300 |
O1—C1 | 1.244 (3) | C11—C19 | 1.488 (3) |
N1—C1 | 1.377 (3) | C12—C17 | 1.389 (3) |
N1—N2 | 1.396 (2) | C12—C13 | 1.390 (3) |
N1—C5 | 1.419 (3) | C13—C14 | 1.378 (3) |
N2—C3 | 1.307 (3) | C13—H13 | 0.9300 |
N3—C11 | 1.340 (3) | C14—C15 | 1.381 (3) |
N3—C12 | 1.421 (3) | C14—H14 | 0.9300 |
N3—H3 | 0.8600 | C15—C16 | 1.387 (3) |
C1—C2 | 1.451 (3) | C15—C18 | 1.489 (3) |
C2—C11 | 1.390 (3) | C16—C17 | 1.375 (3) |
C2—C3 | 1.442 (3) | C16—H16 | 0.9300 |
C3—C4 | 1.491 (3) | C17—H17 | 0.9300 |
C4—H4A | 0.9600 | C19—C24 | 1.385 (3) |
C4—H4B | 0.9600 | C19—C20 | 1.390 (3) |
C4—H4C | 0.9600 | C20—C21 | 1.388 (3) |
C5—C10 | 1.380 (3) | C20—H20 | 0.9300 |
C5—C6 | 1.385 (3) | C21—C22 | 1.375 (4) |
C6—C7 | 1.385 (3) | C21—H21 | 0.9300 |
C6—H6 | 0.9300 | C22—C23 | 1.379 (4) |
C7—C8 | 1.379 (4) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | C23—C24 | 1.380 (3) |
C8—C9 | 1.368 (4) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C1—N1—N2 | 112.32 (16) | C17—C12—C13 | 119.5 (2) |
C1—N1—C5 | 127.73 (17) | C17—C12—N3 | 121.8 (2) |
N2—N1—C5 | 119.51 (17) | C13—C12—N3 | 118.66 (19) |
C3—N2—N1 | 106.70 (17) | C14—C13—C12 | 120.2 (2) |
C11—N3—C12 | 128.37 (18) | C14—C13—H13 | 119.9 |
C11—N3—H3 | 115.8 | C12—C13—H13 | 119.9 |
C12—N3—H3 | 115.8 | C13—C14—C15 | 120.2 (2) |
O1—C1—N1 | 126.24 (19) | C13—C14—H14 | 119.9 |
O1—C1—C2 | 129.26 (19) | C15—C14—H14 | 119.9 |
N1—C1—C2 | 104.48 (17) | C14—C15—C16 | 119.7 (2) |
C11—C2—C3 | 132.65 (19) | C14—C15—C18 | 120.9 (2) |
C11—C2—C1 | 122.13 (19) | C16—C15—C18 | 119.4 (2) |
C3—C2—C1 | 104.96 (17) | C17—C16—C15 | 120.5 (2) |
N2—C3—C2 | 111.44 (18) | C17—C16—H16 | 119.8 |
N2—C3—C4 | 118.50 (19) | C15—C16—H16 | 119.8 |
C2—C3—C4 | 130.03 (19) | C16—C17—C12 | 119.9 (2) |
C3—C4—H4A | 109.5 | C16—C17—H17 | 120.1 |
C3—C4—H4B | 109.5 | C12—C17—H17 | 120.1 |
H4A—C4—H4B | 109.5 | F2—C18—F1 | 108.1 (3) |
C3—C4—H4C | 109.5 | F2—C18—F3 | 103.3 (3) |
H4A—C4—H4C | 109.5 | F1—C18—F3 | 104.5 (3) |
H4B—C4—H4C | 109.5 | F2—C18—C15 | 113.4 (2) |
C10—C5—C6 | 120.1 (2) | F1—C18—C15 | 113.1 (2) |
C10—C5—N1 | 119.7 (2) | F3—C18—C15 | 113.5 (3) |
C6—C5—N1 | 120.2 (2) | C24—C19—C20 | 119.8 (2) |
C5—C6—C7 | 119.4 (2) | C24—C19—C11 | 119.31 (19) |
C5—C6—H6 | 120.3 | C20—C19—C11 | 120.87 (19) |
C7—C6—H6 | 120.3 | C21—C20—C19 | 119.4 (2) |
C8—C7—C6 | 120.4 (2) | C21—C20—H20 | 120.3 |
C8—C7—H7 | 119.8 | C19—C20—H20 | 120.3 |
C6—C7—H7 | 119.8 | C22—C21—C20 | 120.5 (2) |
C9—C8—C7 | 119.5 (2) | C22—C21—H21 | 119.8 |
C9—C8—H8 | 120.3 | C20—C21—H21 | 119.8 |
C7—C8—H8 | 120.3 | C21—C22—C23 | 120.0 (2) |
C8—C9—C10 | 121.0 (3) | C21—C22—H22 | 120.0 |
C8—C9—H9 | 119.5 | C23—C22—H22 | 120.0 |
C10—C9—H9 | 119.5 | C22—C23—C24 | 120.1 (2) |
C9—C10—C5 | 119.6 (2) | C22—C23—H23 | 119.9 |
C9—C10—H10 | 120.2 | C24—C23—H23 | 119.9 |
C5—C10—H10 | 120.2 | C23—C24—C19 | 120.2 (2) |
N3—C11—C2 | 118.67 (18) | C23—C24—H24 | 119.9 |
N3—C11—C19 | 118.50 (18) | C19—C24—H24 | 119.9 |
C2—C11—C19 | 122.75 (18) | ||
C1—N1—N2—C3 | −2.4 (2) | C3—C2—C11—C19 | 4.0 (4) |
C5—N1—N2—C3 | −175.31 (18) | C1—C2—C11—C19 | 177.36 (19) |
N2—N1—C1—O1 | −175.1 (2) | C11—N3—C12—C17 | 41.3 (3) |
C5—N1—C1—O1 | −3.0 (4) | C11—N3—C12—C13 | −140.4 (2) |
N2—N1—C1—C2 | 3.3 (2) | C17—C12—C13—C14 | −1.9 (3) |
C5—N1—C1—C2 | 175.43 (19) | N3—C12—C13—C14 | 179.7 (2) |
O1—C1—C2—C11 | 0.6 (4) | C12—C13—C14—C15 | −0.1 (4) |
N1—C1—C2—C11 | −177.68 (19) | C13—C14—C15—C16 | 1.2 (4) |
O1—C1—C2—C3 | 175.5 (2) | C13—C14—C15—C18 | −177.2 (2) |
N1—C1—C2—C3 | −2.8 (2) | C14—C15—C16—C17 | −0.2 (4) |
N1—N2—C3—C2 | 0.5 (2) | C18—C15—C16—C17 | 178.2 (2) |
N1—N2—C3—C4 | 178.7 (2) | C15—C16—C17—C12 | −1.8 (4) |
C11—C2—C3—N2 | 175.6 (2) | C13—C12—C17—C16 | 2.9 (4) |
C1—C2—C3—N2 | 1.5 (2) | N3—C12—C17—C16 | −178.8 (2) |
C11—C2—C3—C4 | −2.4 (4) | C14—C15—C18—F2 | 87.5 (4) |
C1—C2—C3—C4 | −176.5 (2) | C16—C15—C18—F2 | −90.9 (3) |
C1—N1—C5—C10 | 36.3 (3) | C14—C15—C18—F1 | −148.9 (3) |
N2—N1—C5—C10 | −152.0 (2) | C16—C15—C18—F1 | 32.7 (4) |
C1—N1—C5—C6 | −143.6 (2) | C14—C15—C18—F3 | −30.0 (4) |
N2—N1—C5—C6 | 28.1 (3) | C16—C15—C18—F3 | 151.6 (3) |
C10—C5—C6—C7 | −1.3 (3) | N3—C11—C19—C24 | 64.0 (3) |
N1—C5—C6—C7 | 178.6 (2) | C2—C11—C19—C24 | −112.7 (2) |
C5—C6—C7—C8 | 0.4 (4) | N3—C11—C19—C20 | −113.8 (2) |
C6—C7—C8—C9 | 0.6 (4) | C2—C11—C19—C20 | 69.5 (3) |
C7—C8—C9—C10 | −0.7 (4) | C24—C19—C20—C21 | −1.3 (3) |
C8—C9—C10—C5 | −0.2 (4) | C11—C19—C20—C21 | 176.5 (2) |
C6—C5—C10—C9 | 1.2 (4) | C19—C20—C21—C22 | 0.5 (4) |
N1—C5—C10—C9 | −178.6 (2) | C20—C21—C22—C23 | 1.0 (4) |
C12—N3—C11—C2 | −177.2 (2) | C21—C22—C23—C24 | −1.5 (4) |
C12—N3—C11—C19 | 6.0 (3) | C22—C23—C24—C19 | 0.6 (4) |
C3—C2—C11—N3 | −172.6 (2) | C20—C19—C24—C23 | 0.8 (4) |
C1—C2—C11—N3 | 0.7 (3) | C11—C19—C24—C23 | −177.0 (2) |
Experimental details
Crystal data | |
Chemical formula | C24H18F3N3O |
Mr | 421.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 7.6059 (9), 10.9913 (12), 13.8057 (15) |
α, β, γ (°) | 108.448 (2), 100.227 (2), 105.178 (2) |
V (Å3) | 1013.0 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.35 × 0.26 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.964, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5150, 3527, 3079 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.163, 1.00 |
No. of reflections | 3527 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.71, −0.40 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
The title compound, (I), was synthesized as part of a continuing project involving the structures of pyrazolone derivatives. Pyrazolone derivatives are well known for their potential applications in the areas of pharmaceuticals, agrochemicals, dyes, and pigments, and also as chelating agents and extracting agents. Moreover, they are capable of prototropic tautomerism (Akama & Tong, 1996; Eller & Holzer, 2004).
The molecule of (I) exists in enamine-keto tautomeric form in the crystal instead of the imine form (Fig. 1), as in 4-[(Z)-(benzylamino) phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one (Jiang et al., 2004). The central pyrazolone (C1–C3/N1/N2) ring is essentially planar, with an r.m.s. deviation of 0.0116 Å for the fitted atoms. This ring makes dihedral angles of 31.8 (2), 45.4 (2) and 71.2 (2)° with the C5–C10, C12–C17 and C19–C24 phenyl rings, respectively. Similar tautomerism has also been observed in related pyrazolone analogues reported by us previously (Sun et al., 2006, 2007). In addition, the present compound also features an intramolecular hydrogen bond between the N3 and O1 atoms (Table 1), leading to the fact that atoms O1 and N3 are on the same side of the C2–C11 bond, which will be the potential bidentate N,O-chelate positions after deprotonation to form functional complexes as candidates with catalytic applications (Lu et al., 2006).