Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043796/hb2534sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043796/hb2534Isup2.hkl |
CCDC reference: 663749
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.004 Å
- R factor = 0.044
- wR factor = 0.120
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For general background, see: Hu (2006); Kahwa et al. (1986); Klayman et al. (1979); Santos et al. (2001). For reference structural data, see: Allen et al. (1987).
An anhydrous ethanol solution (50 ml) of 4-formylphenyl 4-chlorobenzoate (2.61 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N2, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 87% yield. Yellow blocks of (I) were obtained by slow evaporation of an acetonitrile solution.
The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H and N—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene C—H; 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl C—H.
The synthesis and structure of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al., 1986 and Klayman et al., 1979). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Hu, 2006) has been reported. Such structural information is useful when investigating the potential coordination properties of Schiff bases functioning as ligands. We new report the synthesis and molecular structure of the title Schiff base, (I), (Fig. 1)
In the title molecule (Fig. 1), the pyrazolone ring (C15—C17/N1/N2/N3/O3) is nearly planar, with an r.m.s. deviation for the fitted atoms of 0.038 Å. It makes a dihedral angle of 55.54 (7)° with its attached phenyl ring (C20—C25). The central benzene ring (C8—C14/O1) is almost planar, with an r.m.s. deviation for fitted atoms of 0.017 Å. This group makes dihedral angles of 7.56 (10)°, 39.46 (7)° and 63.03 (7)°, respectively, with the the pyrazolone ring (C15—C17/N1/N2/N3/O3), the terminal C1—C6 benzene ring and the terminal C20—C25 phenyl ring. Otherwise, all bond lengths and angles are within their normal ranges (Allen et al., 1987).
The packing for (I) is stabilized by weak, non-classical intermolecular C—H···O hydrogen bonds that links molecules into one-dimensional extended chains running along the b axis (Fig. 2, Table 1).
For general background, see: Hu (2006); Kahwa et al. (1986); Klayman et al. (1979); Santos et al. (2001). For reference structural data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. The structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level. | |
Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines. |
C25H20ClN3O3 | F(000) = 1856 |
Mr = 445.89 | Dx = 1.344 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2545 reflections |
a = 31.764 (7) Å | θ = 3.2–24.2° |
b = 6.7113 (16) Å | µ = 0.21 mm−1 |
c = 25.605 (6) Å | T = 294 K |
β = 126.165 (3)° | Block, yellow |
V = 4406.7 (18) Å3 | 0.26 × 0.24 × 0.20 mm |
Z = 8 |
Bruker SMART APEX CCD diffractometer | 3962 independent reflections |
Radiation source: fine-focus sealed tube | 2422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 25.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −38→37 |
Tmin = 0.921, Tmax = 0.960 | k = −8→5 |
10804 measured reflections | l = −30→29 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0549P)2 + 0.4018P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3962 reflections | Δρmax = 0.23 e Å−3 |
292 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0009 (2) |
C25H20ClN3O3 | V = 4406.7 (18) Å3 |
Mr = 445.89 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 31.764 (7) Å | µ = 0.21 mm−1 |
b = 6.7113 (16) Å | T = 294 K |
c = 25.605 (6) Å | 0.26 × 0.24 × 0.20 mm |
β = 126.165 (3)° |
Bruker SMART APEX CCD diffractometer | 3962 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2422 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.960 | Rint = 0.051 |
10804 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.23 e Å−3 |
3962 reflections | Δρmin = −0.21 e Å−3 |
292 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 > 2σ(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 | ||
Cl1 | 0.02921 (3) | 0.85943 (14) | 0.32838 (3) | 0.0868 (3) | |
O1 | 0.06375 (6) | 0.6862 (2) | 0.60622 (7) | 0.0559 (5) | |
O2 | 0.10080 (8) | 0.9908 (3) | 0.62984 (8) | 0.0897 (7) | |
O3 | 0.14117 (6) | 0.6064 (2) | 0.98425 (7) | 0.0527 (4) | |
N1 | 0.14862 (7) | 0.3501 (3) | 0.88646 (8) | 0.0454 (5) | |
N2 | 0.20831 (7) | 0.1617 (3) | 1.04555 (8) | 0.0450 (5) | |
N3 | 0.18559 (7) | 0.3329 (3) | 1.05031 (8) | 0.0423 (5) | |
C1 | 0.07274 (9) | 1.0228 (4) | 0.50268 (11) | 0.0637 (7) | |
H1 | 0.0863 | 1.1358 | 0.5286 | 0.076* | |
C2 | 0.06193 (9) | 1.0265 (5) | 0.44201 (12) | 0.0655 (7) | |
H2 | 0.0678 | 1.1410 | 0.4267 | 0.079* | |
C3 | 0.04222 (8) | 0.8573 (4) | 0.40467 (10) | 0.0548 (7) | |
C4 | 0.03306 (9) | 0.6874 (4) | 0.42588 (11) | 0.0567 (7) | |
H4 | 0.0200 | 0.5742 | 0.4000 | 0.068* | |
C5 | 0.04351 (8) | 0.6865 (4) | 0.48666 (10) | 0.0526 (6) | |
H5 | 0.0369 | 0.5725 | 0.5013 | 0.063* | |
C6 | 0.06368 (8) | 0.8535 (4) | 0.52553 (10) | 0.0475 (6) | |
C7 | 0.07797 (9) | 0.8564 (4) | 0.59202 (11) | 0.0547 (7) | |
C8 | 0.07828 (8) | 0.6511 (4) | 0.66906 (10) | 0.0477 (6) | |
C9 | 0.09811 (9) | 0.4660 (4) | 0.69396 (10) | 0.0545 (6) | |
H9 | 0.1023 | 0.3739 | 0.6702 | 0.065* | |
C10 | 0.11186 (9) | 0.4166 (4) | 0.75437 (11) | 0.0541 (6) | |
H10 | 0.1253 | 0.2907 | 0.7712 | 0.065* | |
C11 | 0.10592 (8) | 0.5522 (4) | 0.79049 (10) | 0.0470 (6) | |
C12 | 0.08446 (9) | 0.7354 (4) | 0.76314 (11) | 0.0601 (7) | |
H12 | 0.0790 | 0.8263 | 0.7860 | 0.072* | |
C13 | 0.07073 (9) | 0.7882 (4) | 0.70247 (11) | 0.0602 (7) | |
H13 | 0.0568 | 0.9131 | 0.6850 | 0.072* | |
C14 | 0.12225 (8) | 0.5065 (4) | 0.85623 (10) | 0.0507 (6) | |
H14 | 0.1132 | 0.5936 | 0.8763 | 0.061* | |
C15 | 0.16474 (8) | 0.3141 (3) | 0.94963 (10) | 0.0391 (5) | |
C16 | 0.19226 (8) | 0.1468 (3) | 0.98340 (10) | 0.0422 (5) | |
C17 | 0.16029 (8) | 0.4388 (3) | 0.99142 (10) | 0.0398 (5) | |
C18 | 0.20356 (9) | −0.0335 (4) | 0.96011 (11) | 0.0579 (7) | |
H18A | 0.2406 | −0.0542 | 0.9857 | 0.087* | |
H18B | 0.1902 | −0.0158 | 0.9156 | 0.087* | |
H18C | 0.1872 | −0.1472 | 0.9640 | 0.087* | |
C19 | 0.21951 (10) | −0.0063 (4) | 1.08845 (11) | 0.0638 (7) | |
H19A | 0.1937 | −0.1081 | 1.0646 | 0.096* | |
H19B | 0.2189 | 0.0382 | 1.1236 | 0.096* | |
H19C | 0.2534 | −0.0593 | 1.1053 | 0.096* | |
C20 | 0.21162 (8) | 0.4321 (3) | 1.11138 (9) | 0.0407 (5) | |
C21 | 0.26530 (9) | 0.4262 (4) | 1.15526 (10) | 0.0491 (6) | |
H21 | 0.2851 | 0.3512 | 1.1466 | 0.059* | |
C22 | 0.28909 (10) | 0.5325 (4) | 1.21193 (11) | 0.0603 (7) | |
H22 | 0.3252 | 0.5284 | 1.2418 | 0.072* | |
C23 | 0.26000 (11) | 0.6446 (4) | 1.22477 (11) | 0.0618 (7) | |
H23 | 0.2764 | 0.7173 | 1.2630 | 0.074* | |
C24 | 0.20683 (11) | 0.6495 (4) | 1.18132 (12) | 0.0603 (7) | |
H24 | 0.1873 | 0.7256 | 1.1902 | 0.072* | |
C25 | 0.18209 (9) | 0.5423 (3) | 1.12451 (11) | 0.0493 (6) | |
H25 | 0.1459 | 0.5441 | 1.0953 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0819 (5) | 0.1383 (8) | 0.0487 (4) | 0.0290 (5) | 0.0433 (4) | 0.0191 (4) |
O1 | 0.0649 (11) | 0.0630 (12) | 0.0327 (8) | −0.0080 (9) | 0.0249 (8) | 0.0011 (8) |
O2 | 0.1223 (16) | 0.0849 (15) | 0.0484 (10) | −0.0433 (13) | 0.0429 (11) | −0.0191 (11) |
O3 | 0.0628 (10) | 0.0451 (10) | 0.0453 (9) | 0.0098 (8) | 0.0292 (8) | 0.0067 (8) |
N1 | 0.0438 (11) | 0.0510 (13) | 0.0350 (10) | −0.0041 (9) | 0.0196 (9) | 0.0035 (9) |
N2 | 0.0558 (12) | 0.0353 (11) | 0.0403 (11) | 0.0024 (9) | 0.0264 (9) | 0.0060 (9) |
N3 | 0.0486 (11) | 0.0378 (11) | 0.0362 (10) | 0.0034 (9) | 0.0227 (9) | 0.0037 (9) |
C1 | 0.0691 (17) | 0.0617 (18) | 0.0473 (15) | −0.0138 (14) | 0.0271 (13) | −0.0019 (13) |
C2 | 0.0658 (17) | 0.076 (2) | 0.0518 (15) | −0.0055 (15) | 0.0329 (14) | 0.0155 (15) |
C3 | 0.0397 (14) | 0.085 (2) | 0.0363 (13) | 0.0086 (13) | 0.0207 (11) | 0.0081 (14) |
C4 | 0.0487 (14) | 0.0705 (19) | 0.0429 (14) | −0.0070 (13) | 0.0226 (12) | −0.0091 (13) |
C5 | 0.0493 (14) | 0.0601 (17) | 0.0431 (14) | −0.0091 (12) | 0.0243 (12) | −0.0016 (12) |
C6 | 0.0403 (13) | 0.0580 (16) | 0.0341 (12) | −0.0036 (12) | 0.0164 (11) | 0.0032 (12) |
C7 | 0.0552 (15) | 0.0600 (17) | 0.0389 (14) | −0.0072 (13) | 0.0223 (13) | 0.0001 (13) |
C8 | 0.0448 (13) | 0.0616 (17) | 0.0300 (11) | 0.0011 (12) | 0.0184 (11) | 0.0051 (12) |
C9 | 0.0619 (15) | 0.0588 (17) | 0.0437 (14) | 0.0055 (13) | 0.0317 (12) | −0.0005 (12) |
C10 | 0.0571 (15) | 0.0557 (16) | 0.0432 (13) | 0.0141 (12) | 0.0260 (12) | 0.0096 (12) |
C11 | 0.0446 (13) | 0.0555 (16) | 0.0337 (12) | 0.0056 (12) | 0.0191 (11) | 0.0051 (11) |
C12 | 0.0730 (17) | 0.0668 (18) | 0.0444 (14) | 0.0189 (14) | 0.0368 (13) | 0.0076 (13) |
C13 | 0.0661 (17) | 0.0648 (18) | 0.0433 (14) | 0.0217 (14) | 0.0288 (13) | 0.0147 (13) |
C14 | 0.0527 (14) | 0.0588 (16) | 0.0394 (13) | 0.0003 (13) | 0.0265 (11) | 0.0000 (12) |
C15 | 0.0404 (12) | 0.0387 (13) | 0.0355 (12) | −0.0043 (10) | 0.0209 (10) | 0.0016 (10) |
C16 | 0.0432 (13) | 0.0396 (14) | 0.0432 (13) | −0.0050 (11) | 0.0253 (11) | 0.0005 (11) |
C17 | 0.0391 (12) | 0.0371 (14) | 0.0380 (12) | −0.0029 (11) | 0.0199 (10) | 0.0040 (11) |
C18 | 0.0743 (17) | 0.0459 (16) | 0.0612 (15) | −0.0013 (13) | 0.0442 (14) | 0.0006 (12) |
C19 | 0.0869 (19) | 0.0444 (16) | 0.0569 (15) | 0.0035 (14) | 0.0406 (14) | 0.0147 (13) |
C20 | 0.0519 (14) | 0.0370 (13) | 0.0339 (12) | −0.0030 (11) | 0.0256 (11) | 0.0046 (10) |
C21 | 0.0502 (14) | 0.0572 (16) | 0.0397 (13) | 0.0006 (12) | 0.0264 (12) | 0.0057 (12) |
C22 | 0.0559 (15) | 0.0743 (19) | 0.0383 (13) | −0.0053 (14) | 0.0209 (12) | 0.0025 (13) |
C23 | 0.079 (2) | 0.0604 (18) | 0.0393 (14) | −0.0069 (15) | 0.0313 (15) | −0.0047 (12) |
C24 | 0.082 (2) | 0.0554 (17) | 0.0581 (16) | 0.0026 (14) | 0.0494 (16) | −0.0023 (14) |
C25 | 0.0543 (14) | 0.0489 (15) | 0.0480 (13) | −0.0005 (12) | 0.0320 (12) | 0.0043 (12) |
Cl1—C3 | 1.742 (2) | C10—H10 | 0.9300 |
O1—C7 | 1.355 (3) | C11—C12 | 1.380 (3) |
O1—C8 | 1.408 (2) | C11—C14 | 1.472 (3) |
O2—C7 | 1.204 (3) | C12—C13 | 1.389 (3) |
O3—C17 | 1.239 (3) | C12—H12 | 0.9300 |
N1—C14 | 1.280 (3) | C13—H13 | 0.9300 |
N1—C15 | 1.400 (3) | C14—H14 | 0.9300 |
N2—C16 | 1.358 (3) | C15—C16 | 1.371 (3) |
N2—N3 | 1.400 (2) | C15—C17 | 1.430 (3) |
N2—C19 | 1.464 (3) | C16—C18 | 1.484 (3) |
N3—C17 | 1.412 (3) | C18—H18A | 0.9600 |
N3—C20 | 1.431 (3) | C18—H18B | 0.9600 |
C1—C2 | 1.379 (3) | C18—H18C | 0.9600 |
C1—C6 | 1.384 (3) | C19—H19A | 0.9600 |
C1—H1 | 0.9300 | C19—H19B | 0.9600 |
C2—C3 | 1.375 (4) | C19—H19C | 0.9600 |
C2—H2 | 0.9300 | C20—C21 | 1.382 (3) |
C3—C4 | 1.366 (3) | C20—C25 | 1.383 (3) |
C4—C5 | 1.386 (3) | C21—C22 | 1.375 (3) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.380 (3) | C22—C23 | 1.374 (3) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—C7 | 1.481 (3) | C23—C24 | 1.369 (3) |
C8—C9 | 1.368 (3) | C23—H23 | 0.9300 |
C8—C13 | 1.371 (3) | C24—C25 | 1.379 (3) |
C9—C10 | 1.377 (3) | C24—H24 | 0.9300 |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.387 (3) | ||
C7—O1—C8 | 120.77 (18) | C8—C13—H13 | 120.9 |
C14—N1—C15 | 120.2 (2) | C12—C13—H13 | 120.9 |
C16—N2—N3 | 107.82 (16) | N1—C14—C11 | 121.7 (2) |
C16—N2—C19 | 125.42 (19) | N1—C14—H14 | 119.1 |
N3—N2—C19 | 118.44 (18) | C11—C14—H14 | 119.1 |
N2—N3—C17 | 108.53 (17) | C16—C15—N1 | 122.2 (2) |
N2—N3—C20 | 118.83 (16) | C16—C15—C17 | 108.37 (19) |
C17—N3—C20 | 122.04 (18) | N1—C15—C17 | 129.3 (2) |
C2—C1—C6 | 121.0 (2) | N2—C16—C15 | 109.73 (19) |
C2—C1—H1 | 119.5 | N2—C16—C18 | 121.21 (19) |
C6—C1—H1 | 119.5 | C15—C16—C18 | 129.0 (2) |
C3—C2—C1 | 118.5 (2) | O3—C17—N3 | 122.4 (2) |
C3—C2—H2 | 120.8 | O3—C17—C15 | 132.6 (2) |
C1—C2—H2 | 120.8 | N3—C17—C15 | 105.01 (19) |
C4—C3—C2 | 122.0 (2) | C16—C18—H18A | 109.5 |
C4—C3—Cl1 | 119.2 (2) | C16—C18—H18B | 109.5 |
C2—C3—Cl1 | 118.9 (2) | H18A—C18—H18B | 109.5 |
C3—C4—C5 | 118.9 (2) | C16—C18—H18C | 109.5 |
C3—C4—H4 | 120.5 | H18A—C18—H18C | 109.5 |
C5—C4—H4 | 120.5 | H18B—C18—H18C | 109.5 |
C6—C5—C4 | 120.5 (2) | N2—C19—H19A | 109.5 |
C6—C5—H5 | 119.7 | N2—C19—H19B | 109.5 |
C4—C5—H5 | 119.7 | H19A—C19—H19B | 109.5 |
C5—C6—C1 | 119.1 (2) | N2—C19—H19C | 109.5 |
C5—C6—C7 | 122.5 (2) | H19A—C19—H19C | 109.5 |
C1—C6—C7 | 118.4 (2) | H19B—C19—H19C | 109.5 |
O2—C7—O1 | 123.7 (2) | C21—C20—C25 | 120.4 (2) |
O2—C7—C6 | 124.4 (2) | C21—C20—N3 | 121.0 (2) |
O1—C7—C6 | 111.9 (2) | C25—C20—N3 | 118.50 (19) |
C9—C8—C13 | 121.4 (2) | C22—C21—C20 | 119.3 (2) |
C9—C8—O1 | 115.8 (2) | C22—C21—H21 | 120.4 |
C13—C8—O1 | 122.7 (2) | C20—C21—H21 | 120.4 |
C8—C9—C10 | 119.7 (2) | C23—C22—C21 | 120.6 (2) |
C8—C9—H9 | 120.1 | C23—C22—H22 | 119.7 |
C10—C9—H9 | 120.1 | C21—C22—H22 | 119.7 |
C9—C10—C11 | 120.9 (2) | C24—C23—C22 | 120.0 (2) |
C9—C10—H10 | 119.6 | C24—C23—H23 | 120.0 |
C11—C10—H10 | 119.6 | C22—C23—H23 | 120.0 |
C12—C11—C10 | 117.8 (2) | C23—C24—C25 | 120.4 (2) |
C12—C11—C14 | 120.1 (2) | C23—C24—H24 | 119.8 |
C10—C11—C14 | 122.1 (2) | C25—C24—H24 | 119.8 |
C11—C12—C13 | 122.0 (2) | C24—C25—C20 | 119.3 (2) |
C11—C12—H12 | 119.0 | C24—C25—H25 | 120.4 |
C13—C12—H12 | 119.0 | C20—C25—H25 | 120.4 |
C8—C13—C12 | 118.1 (2) | ||
C16—N2—N3—C17 | −7.5 (2) | C12—C11—C14—N1 | −170.3 (2) |
C19—N2—N3—C17 | −157.56 (18) | C10—C11—C14—N1 | 9.0 (3) |
C16—N2—N3—C20 | −152.92 (18) | C14—N1—C15—C16 | 178.8 (2) |
C19—N2—N3—C20 | 57.0 (3) | C14—N1—C15—C17 | −6.2 (3) |
C6—C1—C2—C3 | −0.5 (4) | N3—N2—C16—C15 | 6.8 (2) |
C1—C2—C3—C4 | 0.1 (4) | C19—N2—C16—C15 | 154.1 (2) |
C1—C2—C3—Cl1 | −179.20 (19) | N3—N2—C16—C18 | −171.50 (19) |
C2—C3—C4—C5 | 0.6 (4) | C19—N2—C16—C18 | −24.1 (3) |
Cl1—C3—C4—C5 | 179.97 (17) | N1—C15—C16—N2 | 172.45 (18) |
C3—C4—C5—C6 | −1.1 (3) | C17—C15—C16—N2 | −3.4 (2) |
C4—C5—C6—C1 | 0.8 (3) | N1—C15—C16—C18 | −9.5 (4) |
C4—C5—C6—C7 | −176.8 (2) | C17—C15—C16—C18 | 174.7 (2) |
C2—C1—C6—C5 | 0.0 (4) | N2—N3—C17—O3 | −172.80 (18) |
C2—C1—C6—C7 | 177.7 (2) | C20—N3—C17—O3 | −28.7 (3) |
C8—O1—C7—O2 | −4.2 (4) | N2—N3—C17—C15 | 5.3 (2) |
C8—O1—C7—C6 | 173.80 (18) | C20—N3—C17—C15 | 149.38 (19) |
C5—C6—C7—O2 | 171.5 (3) | C16—C15—C17—O3 | 176.6 (2) |
C1—C6—C7—O2 | −6.1 (4) | N1—C15—C17—O3 | 1.1 (4) |
C5—C6—C7—O1 | −6.5 (3) | C16—C15—C17—N3 | −1.3 (2) |
C1—C6—C7—O1 | 175.9 (2) | N1—C15—C17—N3 | −176.73 (19) |
C7—O1—C8—C9 | −133.6 (2) | N2—N3—C20—C21 | 29.5 (3) |
C7—O1—C8—C13 | 49.8 (3) | C17—N3—C20—C21 | −111.0 (2) |
C13—C8—C9—C10 | −1.3 (4) | N2—N3—C20—C25 | −153.43 (19) |
O1—C8—C9—C10 | −178.0 (2) | C17—N3—C20—C25 | 66.0 (3) |
C8—C9—C10—C11 | 0.0 (4) | C25—C20—C21—C22 | −0.5 (3) |
C9—C10—C11—C12 | 1.8 (4) | N3—C20—C21—C22 | 176.4 (2) |
C9—C10—C11—C14 | −177.5 (2) | C20—C21—C22—C23 | −0.5 (4) |
C10—C11—C12—C13 | −2.3 (4) | C21—C22—C23—C24 | 0.7 (4) |
C14—C11—C12—C13 | 177.0 (2) | C22—C23—C24—C25 | 0.0 (4) |
C9—C8—C13—C12 | 0.9 (4) | C23—C24—C25—C20 | −1.0 (4) |
O1—C8—C13—C12 | 177.3 (2) | C21—C20—C25—C24 | 1.3 (3) |
C11—C12—C13—C8 | 1.0 (4) | N3—C20—C25—C24 | −175.8 (2) |
C15—N1—C14—C11 | 178.23 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18C···O3i | 0.96 | 2.46 | 3.405 (3) | 169 |
C19—H19A···O3i | 0.96 | 2.58 | 3.497 (3) | 161 |
C2—H2···O3ii | 0.93 | 2.53 | 3.219 (3) | 131 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H20ClN3O3 |
Mr | 445.89 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 31.764 (7), 6.7113 (16), 25.605 (6) |
β (°) | 126.165 (3) |
V (Å3) | 4406.7 (18) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.26 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.921, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10804, 3962, 2422 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.120, 1.03 |
No. of reflections | 3962 |
No. of parameters | 292 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.21 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18C···O3i | 0.96 | 2.46 | 3.405 (3) | 169 |
C19—H19A···O3i | 0.96 | 2.58 | 3.497 (3) | 161 |
C2—H2···O3ii | 0.93 | 2.53 | 3.219 (3) | 131 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2. |
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The synthesis and structure of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al., 1986 and Klayman et al., 1979). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Hu, 2006) has been reported. Such structural information is useful when investigating the potential coordination properties of Schiff bases functioning as ligands. We new report the synthesis and molecular structure of the title Schiff base, (I), (Fig. 1)
In the title molecule (Fig. 1), the pyrazolone ring (C15—C17/N1/N2/N3/O3) is nearly planar, with an r.m.s. deviation for the fitted atoms of 0.038 Å. It makes a dihedral angle of 55.54 (7)° with its attached phenyl ring (C20—C25). The central benzene ring (C8—C14/O1) is almost planar, with an r.m.s. deviation for fitted atoms of 0.017 Å. This group makes dihedral angles of 7.56 (10)°, 39.46 (7)° and 63.03 (7)°, respectively, with the the pyrazolone ring (C15—C17/N1/N2/N3/O3), the terminal C1—C6 benzene ring and the terminal C20—C25 phenyl ring. Otherwise, all bond lengths and angles are within their normal ranges (Allen et al., 1987).
The packing for (I) is stabilized by weak, non-classical intermolecular C—H···O hydrogen bonds that links molecules into one-dimensional extended chains running along the b axis (Fig. 2, Table 1).