Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029624/jh6017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029624/jh6017Isup2.hkl |
CCDC reference: 287615
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.094
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
An anhydrous ethanol solution of 2,4-dichlorobenzaldehyde (1.75 g, 10 mmol) was added to an anhydrous ethanol solution of 4-amino-1,5-dimethyl-2-phenylpyrazolidin-3-one (2.03 g, 10 mmol), and the mixture was stirred at 350 K for 5 h under nitrogen. A yellow precipitate appeared. The product was isolated, recrystallized from ethanol and then dried in vacuo to give pure compound (I) in 78% yield. Bright-yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution of (I).
H atoms were included in calculated positions and refined using a riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH; C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl CH3].
Data collection: SMART (Bruker, 1999); cell refinement: SMART; 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.
C18H15Cl2N3O | F(000) = 744 |
Mr = 360.23 | Dx = 1.426 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4236 (7) Å | Cell parameters from 3316 reflections |
b = 7.3711 (5) Å | θ = 2.9–25.3° |
c = 24.5011 (18) Å | µ = 0.40 mm−1 |
β = 99.693 (1)° | T = 294 K |
V = 1677.6 (2) Å3 | Block, yellow |
Z = 4 | 0.44 × 0.32 × 0.24 mm |
Bruker SMART CCD area-detector diffractometer | 2935 independent reflections |
Radiation source: fine-focus sealed tube | 2235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −11→11 |
Tmin = 0.802, Tmax = 0.909 | k = −8→8 |
8814 measured reflections | l = −26→29 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.3505P] where P = (Fo2 + 2Fc2)/3 |
2935 reflections | (Δ/σ)max = 0.001 |
219 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C18H15Cl2N3O | V = 1677.6 (2) Å3 |
Mr = 360.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.4236 (7) Å | µ = 0.40 mm−1 |
b = 7.3711 (5) Å | T = 294 K |
c = 24.5011 (18) Å | 0.44 × 0.32 × 0.24 mm |
β = 99.693 (1)° |
Bruker SMART CCD area-detector diffractometer | 2935 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2235 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 0.909 | Rint = 0.022 |
8814 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.19 e Å−3 |
2935 reflections | Δρmin = −0.29 e Å−3 |
219 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 | ||
Cl1 | 0.44691 (6) | −0.05518 (7) | 1.06469 (2) | 0.06103 (19) | |
Cl2 | 0.81732 (6) | 0.27063 (10) | 1.22497 (2) | 0.0750 (2) | |
C11 | 0.0882 (2) | 0.8016 (3) | 0.98549 (9) | 0.0506 (5) | |
H11A | 0.1237 | 0.8969 | 0.9648 | 0.076* | |
H11B | 0.1485 | 0.7912 | 1.0211 | 0.076* | |
H11C | −0.0085 | 0.8290 | 0.9903 | 0.076* | |
N1 | 0.03425 (16) | 0.4330 (2) | 0.88548 (6) | 0.0409 (4) | |
N2 | −0.00620 (16) | 0.5959 (2) | 0.90848 (6) | 0.0401 (4) | |
N3 | 0.28447 (15) | 0.4723 (2) | 1.01440 (6) | 0.0382 (4) | |
C1 | 0.46740 (19) | 0.3109 (2) | 1.07464 (7) | 0.0373 (4) | |
C2 | 0.5203 (2) | 0.1435 (3) | 1.09530 (8) | 0.0423 (5) | |
C3 | 0.6284 (2) | 0.1288 (3) | 1.14104 (8) | 0.0506 (5) | |
H3 | 0.6636 | 0.0160 | 1.1538 | 0.061* | |
C4 | 0.6822 (2) | 0.2856 (3) | 1.16710 (8) | 0.0483 (5) | |
C5 | 0.6326 (2) | 0.4533 (3) | 1.14840 (8) | 0.0476 (5) | |
H5 | 0.6698 | 0.5579 | 1.1667 | 0.057* | |
C6 | 0.5271 (2) | 0.4646 (3) | 1.10224 (8) | 0.0432 (5) | |
H6 | 0.4950 | 0.5783 | 1.0892 | 0.052* | |
C7 | 0.35588 (19) | 0.3251 (2) | 1.02526 (7) | 0.0391 (4) | |
H7 | 0.3368 | 0.2262 | 1.0016 | 0.047* | |
C8 | 0.18082 (18) | 0.4828 (2) | 0.96690 (7) | 0.0354 (4) | |
C9 | 0.08972 (19) | 0.6280 (2) | 0.95513 (7) | 0.0370 (4) | |
C10 | 0.14472 (19) | 0.3513 (2) | 0.92327 (7) | 0.0385 (4) | |
O1 | 0.19010 (15) | 0.19821 (18) | 0.91639 (6) | 0.0526 (4) | |
C12 | −0.0797 (2) | 0.7352 (3) | 0.87217 (9) | 0.0567 (6) | |
H12A | −0.1233 | 0.8212 | 0.8937 | 0.085* | |
H12B | −0.1528 | 0.6801 | 0.8453 | 0.085* | |
H12C | −0.0115 | 0.7963 | 0.8536 | 0.085* | |
C13 | −0.0674 (2) | 0.3308 (2) | 0.84841 (7) | 0.0401 (4) | |
C14 | −0.0177 (2) | 0.2350 (3) | 0.80691 (8) | 0.0522 (5) | |
H14 | 0.0783 | 0.2434 | 0.8027 | 0.063* | |
C15 | −0.1117 (3) | 0.1268 (3) | 0.77185 (9) | 0.0634 (6) | |
H15 | −0.0788 | 0.0615 | 0.7440 | 0.076* | |
C16 | −0.2532 (3) | 0.1153 (3) | 0.77790 (9) | 0.0634 (6) | |
H16 | −0.3160 | 0.0411 | 0.7544 | 0.076* | |
C17 | −0.3025 (2) | 0.2133 (3) | 0.81859 (9) | 0.0609 (6) | |
H17 | −0.3992 | 0.2074 | 0.8219 | 0.073* | |
C18 | −0.2097 (2) | 0.3205 (3) | 0.85452 (8) | 0.0502 (5) | |
H18 | −0.2429 | 0.3849 | 0.8825 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0749 (4) | 0.0349 (3) | 0.0688 (4) | 0.0005 (2) | −0.0010 (3) | 0.0033 (2) |
Cl2 | 0.0586 (4) | 0.1057 (5) | 0.0524 (3) | 0.0053 (3) | −0.0145 (3) | 0.0102 (3) |
C11 | 0.0579 (13) | 0.0362 (11) | 0.0545 (12) | 0.0072 (9) | 0.0000 (10) | −0.0071 (9) |
N1 | 0.0411 (9) | 0.0369 (8) | 0.0417 (9) | 0.0088 (7) | −0.0021 (7) | −0.0070 (7) |
N2 | 0.0436 (9) | 0.0316 (8) | 0.0421 (9) | 0.0093 (7) | −0.0016 (7) | −0.0014 (7) |
N3 | 0.0379 (8) | 0.0362 (9) | 0.0382 (8) | 0.0043 (7) | 0.0002 (7) | −0.0002 (7) |
C1 | 0.0360 (10) | 0.0365 (10) | 0.0390 (10) | 0.0048 (8) | 0.0053 (8) | 0.0031 (8) |
C2 | 0.0441 (11) | 0.0368 (11) | 0.0453 (11) | 0.0026 (8) | 0.0057 (9) | 0.0035 (8) |
C3 | 0.0493 (12) | 0.0500 (12) | 0.0504 (12) | 0.0101 (10) | 0.0020 (10) | 0.0131 (10) |
C4 | 0.0374 (11) | 0.0660 (14) | 0.0395 (11) | 0.0035 (10) | 0.0009 (9) | 0.0073 (10) |
C5 | 0.0431 (11) | 0.0498 (12) | 0.0481 (12) | −0.0034 (9) | 0.0020 (9) | −0.0044 (10) |
C6 | 0.0432 (11) | 0.0365 (11) | 0.0483 (11) | 0.0039 (8) | 0.0029 (9) | 0.0014 (9) |
C7 | 0.0399 (10) | 0.0358 (10) | 0.0396 (10) | 0.0026 (8) | 0.0005 (8) | −0.0016 (8) |
C8 | 0.0366 (10) | 0.0320 (9) | 0.0363 (10) | 0.0034 (8) | 0.0029 (8) | −0.0003 (7) |
C9 | 0.0394 (10) | 0.0306 (9) | 0.0396 (10) | 0.0012 (8) | 0.0028 (8) | 0.0003 (8) |
C10 | 0.0371 (10) | 0.0357 (10) | 0.0407 (10) | 0.0055 (8) | 0.0014 (8) | 0.0004 (8) |
O1 | 0.0561 (9) | 0.0393 (8) | 0.0568 (9) | 0.0165 (7) | −0.0064 (7) | −0.0112 (6) |
C12 | 0.0669 (14) | 0.0482 (13) | 0.0505 (13) | 0.0213 (11) | −0.0036 (11) | 0.0082 (10) |
C13 | 0.0437 (11) | 0.0380 (10) | 0.0350 (10) | 0.0044 (8) | −0.0039 (8) | −0.0001 (8) |
C14 | 0.0519 (12) | 0.0560 (13) | 0.0465 (12) | 0.0063 (10) | 0.0020 (10) | −0.0098 (10) |
C15 | 0.0748 (17) | 0.0605 (15) | 0.0508 (13) | 0.0085 (12) | −0.0014 (12) | −0.0173 (11) |
C16 | 0.0762 (17) | 0.0577 (14) | 0.0479 (13) | −0.0105 (12) | −0.0138 (12) | −0.0039 (11) |
C17 | 0.0474 (12) | 0.0814 (17) | 0.0491 (13) | −0.0108 (12) | −0.0056 (10) | 0.0055 (12) |
C18 | 0.0468 (12) | 0.0630 (14) | 0.0387 (11) | 0.0011 (10) | 0.0015 (9) | −0.0008 (10) |
Cl1—C2 | 1.735 (2) | C5—H5 | 0.9300 |
Cl2—C4 | 1.742 (2) | C6—H6 | 0.9300 |
C11—C9 | 1.481 (3) | C7—H7 | 0.9300 |
C11—H11A | 0.9600 | C8—C9 | 1.372 (2) |
C11—H11B | 0.9600 | C8—C10 | 1.440 (2) |
C11—H11C | 0.9600 | C10—O1 | 1.229 (2) |
N1—N2 | 1.406 (2) | C12—H12A | 0.9600 |
N1—C10 | 1.407 (2) | C12—H12B | 0.9600 |
N1—C13 | 1.420 (2) | C12—H12C | 0.9600 |
N2—C9 | 1.353 (2) | C13—C18 | 1.377 (3) |
N2—C12 | 1.456 (2) | C13—C14 | 1.383 (3) |
N3—C7 | 1.281 (2) | C14—C15 | 1.379 (3) |
N3—C8 | 1.390 (2) | C14—H14 | 0.9300 |
C1—C6 | 1.389 (3) | C15—C16 | 1.369 (3) |
C1—C2 | 1.394 (3) | C15—H15 | 0.9300 |
C1—C7 | 1.467 (2) | C16—C17 | 1.374 (3) |
C2—C3 | 1.386 (3) | C16—H16 | 0.9300 |
C3—C4 | 1.375 (3) | C17—C18 | 1.380 (3) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.373 (3) | C18—H18 | 0.9300 |
C5—C6 | 1.377 (3) | ||
C9—C11—H11A | 109.5 | C9—C8—N3 | 123.10 (16) |
C9—C11—H11B | 109.5 | C9—C8—C10 | 107.91 (15) |
H11A—C11—H11B | 109.5 | N3—C8—C10 | 128.97 (16) |
C9—C11—H11C | 109.5 | N2—C9—C8 | 110.28 (15) |
H11A—C11—H11C | 109.5 | N2—C9—C11 | 120.91 (16) |
H11B—C11—H11C | 109.5 | C8—C9—C11 | 128.81 (17) |
N2—N1—C10 | 108.80 (14) | O1—C10—N1 | 122.62 (16) |
N2—N1—C13 | 120.67 (14) | O1—C10—C8 | 132.50 (17) |
C10—N1—C13 | 122.58 (15) | N1—C10—C8 | 104.87 (15) |
C9—N2—N1 | 107.46 (13) | N2—C12—H12A | 109.5 |
C9—N2—C12 | 125.05 (16) | N2—C12—H12B | 109.5 |
N1—N2—C12 | 119.41 (15) | H12A—C12—H12B | 109.5 |
C7—N3—C8 | 119.45 (15) | N2—C12—H12C | 109.5 |
C6—C1—C2 | 117.03 (17) | H12A—C12—H12C | 109.5 |
C6—C1—C7 | 121.27 (16) | H12B—C12—H12C | 109.5 |
C2—C1—C7 | 121.69 (17) | C18—C13—C14 | 120.56 (18) |
C3—C2—C1 | 122.12 (18) | C18—C13—N1 | 121.62 (16) |
C3—C2—Cl1 | 117.99 (15) | C14—C13—N1 | 117.77 (17) |
C1—C2—Cl1 | 119.87 (15) | C15—C14—C13 | 119.5 (2) |
C4—C3—C2 | 118.27 (19) | C15—C14—H14 | 120.3 |
C4—C3—H3 | 120.9 | C13—C14—H14 | 120.3 |
C2—C3—H3 | 120.9 | C16—C15—C14 | 120.2 (2) |
C5—C4—C3 | 121.57 (18) | C16—C15—H15 | 119.9 |
C5—C4—Cl2 | 119.31 (17) | C14—C15—H15 | 119.9 |
C3—C4—Cl2 | 119.12 (16) | C15—C16—C17 | 120.0 (2) |
C4—C5—C6 | 119.14 (19) | C15—C16—H16 | 120.0 |
C4—C5—H5 | 120.4 | C17—C16—H16 | 120.0 |
C6—C5—H5 | 120.4 | C16—C17—C18 | 120.6 (2) |
C5—C6—C1 | 121.87 (18) | C16—C17—H17 | 119.7 |
C5—C6—H6 | 119.1 | C18—C17—H17 | 119.7 |
C1—C6—H6 | 119.1 | C13—C18—C17 | 119.10 (19) |
N3—C7—C1 | 120.66 (17) | C13—C18—H18 | 120.4 |
N3—C7—H7 | 119.7 | C17—C18—H18 | 120.4 |
C1—C7—H7 | 119.7 | ||
C10—N1—N2—C9 | 8.62 (19) | C12—N2—C9—C11 | 24.1 (3) |
C13—N1—N2—C9 | 158.31 (16) | N3—C8—C9—N2 | −175.64 (16) |
C10—N1—N2—C12 | 158.89 (17) | C10—C8—C9—N2 | 2.7 (2) |
C13—N1—N2—C12 | −51.4 (2) | N3—C8—C9—C11 | 5.3 (3) |
C6—C1—C2—C3 | −0.4 (3) | C10—C8—C9—C11 | −176.38 (19) |
C7—C1—C2—C3 | 178.23 (17) | N2—N1—C10—O1 | 172.16 (17) |
C6—C1—C2—Cl1 | 177.69 (14) | C13—N1—C10—O1 | 23.2 (3) |
C7—C1—C2—Cl1 | −3.6 (2) | N2—N1—C10—C8 | −6.80 (19) |
C1—C2—C3—C4 | 1.2 (3) | C13—N1—C10—C8 | −155.80 (16) |
Cl1—C2—C3—C4 | −176.92 (15) | C9—C8—C10—O1 | −176.2 (2) |
C2—C3—C4—C5 | −0.8 (3) | N3—C8—C10—O1 | 2.0 (3) |
C2—C3—C4—Cl2 | 179.59 (14) | C9—C8—C10—N1 | 2.63 (19) |
C3—C4—C5—C6 | −0.4 (3) | N3—C8—C10—N1 | −179.17 (17) |
Cl2—C4—C5—C6 | 179.18 (15) | N2—N1—C13—C18 | −35.2 (3) |
C4—C5—C6—C1 | 1.3 (3) | C10—N1—C13—C18 | 110.3 (2) |
C2—C1—C6—C5 | −0.8 (3) | N2—N1—C13—C14 | 147.44 (18) |
C7—C1—C6—C5 | −179.52 (17) | C10—N1—C13—C14 | −67.1 (2) |
C8—N3—C7—C1 | 179.09 (15) | C18—C13—C14—C15 | −0.7 (3) |
C6—C1—C7—N3 | −18.1 (3) | N1—C13—C14—C15 | 176.71 (19) |
C2—C1—C7—N3 | 163.25 (17) | C13—C14—C15—C16 | 0.4 (4) |
C7—N3—C8—C9 | 173.14 (17) | C14—C15—C16—C17 | 0.7 (4) |
C7—N3—C8—C10 | −4.8 (3) | C15—C16—C17—C18 | −1.6 (4) |
N1—N2—C9—C8 | −7.0 (2) | C14—C13—C18—C17 | −0.1 (3) |
C12—N2—C9—C8 | −155.10 (18) | N1—C13—C18—C17 | −177.43 (19) |
N1—N2—C9—C11 | 172.20 (17) | C16—C17—C18—C13 | 1.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.93 | 2.31 | 3.005 (2) | 131 |
C6—H6···Cl1i | 0.93 | 2.79 | 3.703 (2) | 168 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H15Cl2N3O |
Mr | 360.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 9.4236 (7), 7.3711 (5), 24.5011 (18) |
β (°) | 99.693 (1) |
V (Å3) | 1677.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.44 × 0.32 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.802, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8814, 2935, 2235 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.094, 1.08 |
No. of reflections | 2935 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.29 |
Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Cl1—C2 | 1.735 (2) | N3—C7 | 1.281 (2) |
Cl2—C4 | 1.742 (2) | N3—C8 | 1.390 (2) |
N1—N2 | 1.406 (2) | ||
N2—N1—C10 | 108.80 (14) | C9—N2—C12 | 125.05 (16) |
N2—N1—C13 | 120.67 (14) | N1—N2—C12 | 119.41 (15) |
C10—N1—C13 | 122.58 (15) | C7—N3—C8 | 119.45 (15) |
C9—N2—N1 | 107.46 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.93 | 2.31 | 3.005 (2) | 131.0 |
C6—H6···Cl1i | 0.93 | 2.79 | 3.703 (2) | 168.4 |
Symmetry code: (i) x, y+1, z. |
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Schiff base ligands derived from 4-aminoantipyrine, such as thenoyltrifluoroacetone and 4-hydroxy-3-methoxybenzaldehyde, have been reported (Yu et al., 2002; Diao et al., 2005), which show the synthesis and crystal structure. In the present study, we report the synthesis and structure of the title compound, (I).
In (I) (Fig. 1), the central system (C7–C10/N1–N3/O1) is planar, with an r.m.s. deviation of fitted atoms of 0.0776 Å, and the dihedral angle with the phenyl ring (C13–C18) is 55.98 (6)°. The 2,4-dichlorobenzene group (C1–C7/Cl1/Cl2) is planar, with an r.m.s. deviation of fitted atoms of 0.0192 Å, and the dihedral angle to the central system is 24.25 (5)°. The Cl atoms participate in C—H···Cl interactions (Table 2).