Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051021/hb2589sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051021/hb2589Isup2.hkl |
CCDC reference: 667416
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.133
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C28
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 19
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
An anhydrous ethanol solution (50 ml) of 4-chloro-2-formyl-6-methoxyphenyl 4-methylbenzenesulfonate (3.41 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 85% yield. Yellow blocks of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.
The H atoms were included in calculated positions (C—H = 0.93–0.96 Å) and refined as riding Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986) in areas such as 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-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-ylimino)methyl]-phenyl 4-chlorobenzoate (Han et al., 2007) and (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Hu, 2006) have been reported. We now report the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)
The bond lengths and angles of (I) are within normal ranges (Allen et al., 1987). The pyrazolone ring (C16—C18/N1/N2/N3/O5) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.030 Å. It makes a dihedral angle of 54.45 (9)° with the attached phenyl ring (C21—C26). The o-vanillin group (C8—C13/C15/O3/O4) is almost planar, with an r.m.s. deviation for fitted atoms of 0.020 Å. This group makes dihedral angles of 25.87 (4)°, 11.93 (3)° and 72.05 (7)°, with the the pyrazolone ring (C16—C18/N1/N2/N3/O5), the terminal C1—C6 benzene ring and the terminal C21—C26 phenyl ring, respectively.
The crystal packing is stabilized by weak intermolecular C10—H10···O2═S1 interaction (Table 1, Fig. 2) that form inversion dimers.
For related structures, see: Han et al. (2007); Hu (2006). For general background, see: Kahwa et al. (1986); 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. A packing diagram for (I), with hydrogen bonds drawn as dashed lines. |
C26H24ClN3O5S·C2H3N | Z = 2 |
Mr = 567.06 | F(000) = 592 |
Triclinic, P1 | Dx = 1.349 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3242 (9) Å | Cell parameters from 4430 reflections |
b = 13.2452 (17) Å | θ = 2.8–26.4° |
c = 15.3145 (19) Å | µ = 0.26 mm−1 |
α = 108.731 (2)° | T = 294 K |
β = 93.303 (2)° | Block, yellow |
γ = 94.910 (2)° | 0.24 × 0.22 × 0.18 mm |
V = 1396.1 (3) Å3 |
Bruker SMART APEX CCD diffractometer | 4893 independent reflections |
Radiation source: fine-focus sealed tube | 4057 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.923, Tmax = 0.955 | k = −15→13 |
7152 measured reflections | l = −18→14 |
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) = 0.133 | w = 1/[σ2(Fo2) + (0.0722P)2 + 0.7683P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4893 reflections | Δρmax = 0.72 e Å−3 |
358 parameters | Δρmin = −0.47 e Å−3 |
19 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0160 (19) |
C26H24ClN3O5S·C2H3N | γ = 94.910 (2)° |
Mr = 567.06 | V = 1396.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3242 (9) Å | Mo Kα radiation |
b = 13.2452 (17) Å | µ = 0.26 mm−1 |
c = 15.3145 (19) Å | T = 294 K |
α = 108.731 (2)° | 0.24 × 0.22 × 0.18 mm |
β = 93.303 (2)° |
Bruker SMART APEX CCD diffractometer | 4893 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4057 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.955 | Rint = 0.016 |
7152 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 19 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.72 e Å−3 |
4893 reflections | Δρmin = −0.47 e Å−3 |
358 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 | ||
S1 | 0.62434 (8) | 0.24085 (4) | 0.38970 (4) | 0.03804 (18) | |
Cl1 | 0.72326 (14) | −0.28513 (6) | 0.33595 (5) | 0.0783 (3) | |
O1 | 0.6098 (2) | 0.25614 (14) | 0.30172 (11) | 0.0514 (4) | |
O2 | 0.4724 (2) | 0.18514 (14) | 0.41509 (12) | 0.0509 (4) | |
O3 | 0.8015 (2) | 0.17747 (11) | 0.39394 (10) | 0.0372 (4) | |
O4 | 0.7707 (2) | 0.11000 (14) | 0.53785 (10) | 0.0505 (4) | |
O5 | 0.9284 (2) | 0.18328 (12) | 0.11286 (10) | 0.0453 (4) | |
N1 | 0.7377 (2) | −0.03192 (14) | 0.12557 (11) | 0.0326 (4) | |
N2 | 0.8337 (2) | 0.09923 (14) | −0.04314 (11) | 0.0352 (4) | |
N3 | 0.7241 (2) | 0.00446 (14) | −0.09482 (11) | 0.0346 (4) | |
C1 | 0.6988 (3) | 0.36377 (18) | 0.47552 (15) | 0.0405 (5) | |
C2 | 0.7231 (5) | 0.3682 (2) | 0.56658 (18) | 0.0637 (8) | |
H2 | 0.7062 | 0.3062 | 0.5827 | 0.076* | |
C3 | 0.7733 (5) | 0.4671 (2) | 0.63347 (19) | 0.0702 (8) | |
H3 | 0.7900 | 0.4711 | 0.6952 | 0.084* | |
C4 | 0.7994 (3) | 0.5602 (2) | 0.61129 (19) | 0.0533 (6) | |
C5 | 0.7738 (4) | 0.5527 (2) | 0.52022 (19) | 0.0559 (7) | |
H5 | 0.7901 | 0.6147 | 0.5042 | 0.067* | |
C6 | 0.7242 (4) | 0.45531 (19) | 0.45123 (17) | 0.0494 (6) | |
H6 | 0.7082 | 0.4516 | 0.3896 | 0.059* | |
C7 | 0.8544 (4) | 0.6671 (2) | 0.6855 (2) | 0.0747 (9) | |
H7A | 0.9848 | 0.6758 | 0.7013 | 0.112* | |
H7B | 0.7915 | 0.6699 | 0.7394 | 0.112* | |
H7C | 0.8218 | 0.7236 | 0.6631 | 0.112* | |
C8 | 0.7729 (3) | 0.06603 (17) | 0.37770 (14) | 0.0342 (5) | |
C9 | 0.7623 (3) | 0.03145 (18) | 0.45460 (14) | 0.0386 (5) | |
C10 | 0.7456 (3) | −0.07720 (19) | 0.44131 (15) | 0.0438 (5) | |
H10 | 0.7382 | −0.1023 | 0.4913 | 0.053* | |
C11 | 0.7400 (3) | −0.14827 (18) | 0.35172 (16) | 0.0445 (5) | |
C12 | 0.7497 (3) | −0.11512 (18) | 0.27572 (15) | 0.0392 (5) | |
H12 | 0.7457 | −0.1652 | 0.2168 | 0.047* | |
C13 | 0.7657 (3) | −0.00529 (17) | 0.28775 (14) | 0.0338 (5) | |
C14 | 0.7599 (4) | 0.0782 (2) | 0.61864 (16) | 0.0544 (6) | |
H14A | 0.6451 | 0.0352 | 0.6139 | 0.082* | |
H14B | 0.7678 | 0.1408 | 0.6727 | 0.082* | |
H14C | 0.8597 | 0.0372 | 0.6234 | 0.082* | |
C15 | 0.7817 (3) | 0.03317 (17) | 0.20836 (13) | 0.0332 (4) | |
H15 | 0.8235 | 0.1045 | 0.2179 | 0.040* | |
C16 | 0.7603 (3) | 0.00425 (16) | 0.05086 (13) | 0.0306 (4) | |
C17 | 0.8511 (3) | 0.10494 (17) | 0.04996 (13) | 0.0329 (4) | |
C18 | 0.6926 (3) | −0.05439 (16) | −0.03873 (13) | 0.0318 (4) | |
C19 | 0.6029 (3) | −0.16592 (17) | −0.07583 (15) | 0.0410 (5) | |
H19A | 0.4963 | −0.1690 | −0.1165 | 0.062* | |
H19B | 0.5665 | −0.1893 | −0.0256 | 0.062* | |
H19C | 0.6877 | −0.2119 | −0.1095 | 0.062* | |
C20 | 0.7379 (3) | −0.0387 (2) | −0.19409 (14) | 0.0458 (6) | |
H20A | 0.8540 | −0.0670 | −0.2052 | 0.069* | |
H20B | 0.7292 | 0.0173 | −0.2208 | 0.069* | |
H20C | 0.6398 | −0.0950 | −0.2217 | 0.069* | |
C21 | 0.8404 (3) | 0.19099 (17) | −0.07269 (14) | 0.0365 (5) | |
C22 | 0.6866 (3) | 0.2147 (2) | −0.11566 (17) | 0.0474 (6) | |
H22 | 0.5772 | 0.1695 | −0.1279 | 0.057* | |
C23 | 0.6975 (4) | 0.3068 (2) | −0.1402 (2) | 0.0638 (8) | |
H23 | 0.5953 | 0.3229 | −0.1701 | 0.077* | |
C24 | 0.8578 (5) | 0.3746 (2) | −0.1208 (2) | 0.0693 (8) | |
H24 | 0.8634 | 0.4370 | −0.1365 | 0.083* | |
C25 | 1.0115 (4) | 0.3500 (2) | −0.0779 (2) | 0.0651 (8) | |
H25 | 1.1201 | 0.3961 | −0.0648 | 0.078* | |
C26 | 1.0043 (3) | 0.2575 (2) | −0.05454 (18) | 0.0499 (6) | |
H26 | 1.1081 | 0.2401 | −0.0270 | 0.060* | |
C27 | 0.7594 (6) | 0.4169 (3) | 0.1580 (3) | 0.1074 (14) | |
H27A | 0.8269 | 0.4824 | 0.1979 | 0.161* | |
H27B | 0.8110 | 0.3952 | 0.0995 | 0.161* | |
H27C | 0.7666 | 0.3619 | 0.1861 | 0.161* | |
C28 | 0.5735 (7) | 0.4333 (3) | 0.1443 (4) | 0.128 (2) | |
N4 | 0.4221 (10) | 0.4429 (5) | 0.1437 (5) | 0.186 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0442 (3) | 0.0362 (3) | 0.0308 (3) | −0.0002 (2) | −0.0012 (2) | 0.0088 (2) |
Cl1 | 0.1364 (8) | 0.0419 (4) | 0.0635 (5) | 0.0086 (4) | 0.0092 (4) | 0.0272 (3) |
O1 | 0.0684 (11) | 0.0506 (10) | 0.0334 (9) | 0.0052 (8) | −0.0071 (7) | 0.0135 (7) |
O2 | 0.0449 (9) | 0.0478 (10) | 0.0571 (10) | −0.0033 (7) | 0.0066 (8) | 0.0148 (8) |
O3 | 0.0424 (8) | 0.0357 (8) | 0.0318 (8) | −0.0017 (6) | 0.0012 (6) | 0.0105 (6) |
O4 | 0.0740 (12) | 0.0533 (10) | 0.0236 (8) | 0.0054 (8) | 0.0044 (7) | 0.0124 (7) |
O5 | 0.0603 (10) | 0.0392 (9) | 0.0311 (8) | −0.0092 (7) | −0.0047 (7) | 0.0095 (7) |
N1 | 0.0352 (9) | 0.0366 (9) | 0.0270 (9) | 0.0047 (7) | 0.0025 (7) | 0.0117 (7) |
N2 | 0.0425 (10) | 0.0353 (9) | 0.0273 (9) | −0.0016 (7) | −0.0020 (7) | 0.0120 (7) |
N3 | 0.0436 (10) | 0.0360 (9) | 0.0228 (8) | 0.0016 (8) | −0.0008 (7) | 0.0089 (7) |
C1 | 0.0443 (12) | 0.0382 (12) | 0.0340 (11) | 0.0014 (9) | 0.0008 (9) | 0.0063 (9) |
C2 | 0.102 (2) | 0.0456 (15) | 0.0395 (14) | −0.0013 (14) | −0.0023 (14) | 0.0125 (12) |
C3 | 0.103 (2) | 0.0603 (18) | 0.0353 (14) | 0.0017 (16) | −0.0083 (14) | 0.0029 (12) |
C4 | 0.0465 (14) | 0.0434 (14) | 0.0578 (16) | 0.0052 (11) | 0.0011 (11) | 0.0004 (12) |
C5 | 0.0641 (17) | 0.0380 (13) | 0.0615 (17) | 0.0027 (11) | 0.0072 (13) | 0.0111 (12) |
C6 | 0.0612 (15) | 0.0435 (13) | 0.0434 (13) | 0.0041 (11) | 0.0049 (11) | 0.0143 (11) |
C7 | 0.074 (2) | 0.0527 (17) | 0.073 (2) | 0.0020 (14) | −0.0036 (16) | −0.0105 (15) |
C8 | 0.0371 (11) | 0.0353 (11) | 0.0302 (11) | 0.0017 (9) | 0.0008 (8) | 0.0120 (9) |
C9 | 0.0413 (12) | 0.0490 (13) | 0.0263 (11) | 0.0025 (10) | 0.0012 (9) | 0.0143 (9) |
C10 | 0.0525 (14) | 0.0520 (14) | 0.0342 (12) | 0.0054 (11) | 0.0042 (10) | 0.0241 (10) |
C11 | 0.0557 (14) | 0.0384 (12) | 0.0433 (13) | 0.0037 (10) | 0.0033 (10) | 0.0194 (10) |
C12 | 0.0489 (13) | 0.0366 (11) | 0.0314 (11) | 0.0047 (9) | 0.0015 (9) | 0.0105 (9) |
C13 | 0.0341 (10) | 0.0404 (11) | 0.0272 (10) | 0.0011 (9) | 0.0011 (8) | 0.0125 (9) |
C14 | 0.0636 (16) | 0.0758 (18) | 0.0277 (12) | 0.0086 (13) | 0.0048 (10) | 0.0221 (12) |
C15 | 0.0365 (11) | 0.0351 (11) | 0.0287 (10) | 0.0033 (8) | 0.0033 (8) | 0.0115 (9) |
C16 | 0.0350 (10) | 0.0319 (10) | 0.0252 (10) | 0.0048 (8) | 0.0025 (8) | 0.0095 (8) |
C17 | 0.0360 (11) | 0.0367 (11) | 0.0261 (10) | 0.0040 (9) | 0.0024 (8) | 0.0105 (9) |
C18 | 0.0333 (10) | 0.0340 (11) | 0.0282 (10) | 0.0062 (8) | 0.0041 (8) | 0.0096 (8) |
C19 | 0.0499 (13) | 0.0365 (12) | 0.0325 (11) | −0.0012 (10) | −0.0010 (9) | 0.0079 (9) |
C20 | 0.0576 (14) | 0.0519 (14) | 0.0235 (11) | −0.0006 (11) | 0.0042 (9) | 0.0080 (10) |
C21 | 0.0460 (12) | 0.0376 (11) | 0.0284 (10) | 0.0045 (9) | 0.0054 (9) | 0.0137 (9) |
C22 | 0.0497 (13) | 0.0488 (14) | 0.0466 (14) | 0.0025 (11) | −0.0028 (10) | 0.0214 (11) |
C23 | 0.0738 (19) | 0.0610 (17) | 0.0662 (18) | 0.0118 (14) | −0.0092 (14) | 0.0357 (15) |
C24 | 0.088 (2) | 0.0541 (17) | 0.080 (2) | 0.0037 (15) | 0.0027 (17) | 0.0433 (16) |
C25 | 0.0662 (18) | 0.0571 (17) | 0.080 (2) | −0.0095 (14) | 0.0029 (15) | 0.0378 (15) |
C26 | 0.0478 (14) | 0.0514 (14) | 0.0552 (15) | −0.0004 (11) | 0.0029 (11) | 0.0256 (12) |
C27 | 0.116 (4) | 0.075 (3) | 0.134 (4) | 0.009 (2) | 0.029 (3) | 0.036 (3) |
C28 | 0.123 (4) | 0.046 (2) | 0.217 (6) | 0.015 (2) | 0.049 (4) | 0.038 (3) |
N4 | 0.185 (3) | 0.183 (3) | 0.190 (3) | 0.0223 (11) | 0.0167 (10) | 0.0609 (12) |
S1—O2 | 1.4240 (17) | C10—H10 | 0.9300 |
S1—O1 | 1.4247 (17) | C11—C12 | 1.373 (3) |
S1—O3 | 1.6139 (16) | C12—C13 | 1.400 (3) |
S1—C1 | 1.751 (2) | C12—H12 | 0.9300 |
Cl1—C11 | 1.743 (2) | C13—C15 | 1.468 (3) |
O3—C8 | 1.411 (2) | C14—H14A | 0.9600 |
O4—C9 | 1.356 (3) | C14—H14B | 0.9600 |
O4—C14 | 1.434 (3) | C14—H14C | 0.9600 |
O5—C17 | 1.233 (2) | C15—H15 | 0.9300 |
N1—C15 | 1.288 (3) | C16—C18 | 1.380 (3) |
N1—C16 | 1.388 (3) | C16—C17 | 1.443 (3) |
N2—C17 | 1.401 (3) | C18—C19 | 1.479 (3) |
N2—N3 | 1.401 (2) | C19—H19A | 0.9600 |
N2—C21 | 1.425 (3) | C19—H19B | 0.9600 |
N3—C18 | 1.349 (3) | C19—H19C | 0.9600 |
N3—C20 | 1.455 (3) | C20—H20A | 0.9600 |
C1—C2 | 1.377 (3) | C20—H20B | 0.9600 |
C1—C6 | 1.379 (3) | C20—H20C | 0.9600 |
C2—C3 | 1.384 (4) | C21—C22 | 1.381 (3) |
C2—H2 | 0.9300 | C21—C26 | 1.385 (3) |
C3—C4 | 1.381 (4) | C22—C23 | 1.385 (4) |
C3—H3 | 0.9300 | C22—H22 | 0.9300 |
C4—C5 | 1.367 (4) | C23—C24 | 1.372 (4) |
C4—C7 | 1.509 (4) | C23—H23 | 0.9300 |
C5—C6 | 1.383 (3) | C24—C25 | 1.386 (4) |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C26 | 1.380 (4) |
C7—H7A | 0.9600 | C25—H25 | 0.9300 |
C7—H7B | 0.9600 | C26—H26 | 0.9300 |
C7—H7C | 0.9600 | C27—C28 | 1.411 (6) |
C8—C13 | 1.393 (3) | C27—H27A | 0.9600 |
C8—C9 | 1.398 (3) | C27—H27B | 0.9600 |
C9—C10 | 1.381 (3) | C27—H27C | 0.9600 |
C10—C11 | 1.388 (3) | C28—N4 | 1.126 (7) |
O2—S1—O1 | 118.58 (11) | C12—C13—C15 | 120.92 (19) |
O2—S1—O3 | 107.79 (9) | O4—C14—H14A | 109.5 |
O1—S1—O3 | 107.52 (9) | O4—C14—H14B | 109.5 |
O2—S1—C1 | 111.84 (11) | H14A—C14—H14B | 109.5 |
O1—S1—C1 | 109.30 (11) | O4—C14—H14C | 109.5 |
O3—S1—C1 | 100.09 (9) | H14A—C14—H14C | 109.5 |
C8—O3—S1 | 118.42 (12) | H14B—C14—H14C | 109.5 |
C9—O4—C14 | 117.70 (19) | N1—C15—C13 | 119.96 (19) |
C15—N1—C16 | 119.45 (18) | N1—C15—H15 | 120.0 |
C17—N2—N3 | 109.06 (16) | C13—C15—H15 | 120.0 |
C17—N2—C21 | 123.68 (17) | C18—C16—N1 | 123.36 (18) |
N3—N2—C21 | 120.39 (16) | C18—C16—C17 | 107.84 (17) |
C18—N3—N2 | 107.95 (15) | N1—C16—C17 | 128.80 (17) |
C18—N3—C20 | 125.35 (18) | O5—C17—N2 | 123.64 (19) |
N2—N3—C20 | 118.97 (17) | O5—C17—C16 | 131.51 (19) |
C2—C1—C6 | 121.1 (2) | N2—C17—C16 | 104.84 (16) |
C2—C1—S1 | 119.46 (19) | N3—C18—C16 | 109.78 (18) |
C6—C1—S1 | 119.36 (18) | N3—C18—C19 | 121.14 (18) |
C1—C2—C3 | 118.3 (3) | C16—C18—C19 | 129.05 (19) |
C1—C2—H2 | 120.9 | C18—C19—H19A | 109.5 |
C3—C2—H2 | 120.9 | C18—C19—H19B | 109.5 |
C4—C3—C2 | 122.0 (3) | H19A—C19—H19B | 109.5 |
C4—C3—H3 | 119.0 | C18—C19—H19C | 109.5 |
C2—C3—H3 | 119.0 | H19A—C19—H19C | 109.5 |
C5—C4—C3 | 118.1 (2) | H19B—C19—H19C | 109.5 |
C5—C4—C7 | 121.0 (3) | N3—C20—H20A | 109.5 |
C3—C4—C7 | 120.9 (3) | N3—C20—H20B | 109.5 |
C4—C5—C6 | 121.7 (3) | H20A—C20—H20B | 109.5 |
C4—C5—H5 | 119.1 | N3—C20—H20C | 109.5 |
C6—C5—H5 | 119.1 | H20A—C20—H20C | 109.5 |
C1—C6—C5 | 118.8 (2) | H20B—C20—H20C | 109.5 |
C1—C6—H6 | 120.6 | C22—C21—C26 | 120.9 (2) |
C5—C6—H6 | 120.6 | C22—C21—N2 | 121.1 (2) |
C4—C7—H7A | 109.5 | C26—C21—N2 | 117.9 (2) |
C4—C7—H7B | 109.5 | C21—C22—C23 | 119.1 (2) |
H7A—C7—H7B | 109.5 | C21—C22—H22 | 120.4 |
C4—C7—H7C | 109.5 | C23—C22—H22 | 120.4 |
H7A—C7—H7C | 109.5 | C24—C23—C22 | 120.5 (3) |
H7B—C7—H7C | 109.5 | C24—C23—H23 | 119.7 |
C13—C8—C9 | 122.4 (2) | C22—C23—H23 | 119.7 |
C13—C8—O3 | 119.87 (18) | C23—C24—C25 | 119.9 (3) |
C9—C8—O3 | 117.69 (18) | C23—C24—H24 | 120.0 |
O4—C9—C10 | 125.18 (19) | C25—C24—H24 | 120.0 |
O4—C9—C8 | 115.8 (2) | C26—C25—C24 | 120.3 (3) |
C10—C9—C8 | 119.0 (2) | C26—C25—H25 | 119.8 |
C9—C10—C11 | 118.6 (2) | C24—C25—H25 | 119.8 |
C9—C10—H10 | 120.7 | C25—C26—C21 | 119.1 (2) |
C11—C10—H10 | 120.7 | C25—C26—H26 | 120.5 |
C12—C11—C10 | 122.8 (2) | C21—C26—H26 | 120.5 |
C12—C11—Cl1 | 118.97 (18) | C28—C27—H27A | 109.5 |
C10—C11—Cl1 | 118.23 (18) | C28—C27—H27B | 109.5 |
C11—C12—C13 | 119.4 (2) | H27A—C27—H27B | 109.5 |
C11—C12—H12 | 120.3 | C28—C27—H27C | 109.5 |
C13—C12—H12 | 120.3 | H27A—C27—H27C | 109.5 |
C8—C13—C12 | 117.77 (19) | H27B—C27—H27C | 109.5 |
C8—C13—C15 | 121.27 (19) | N4—C28—C27 | 170.8 (7) |
O2—S1—O3—C8 | 28.54 (16) | O3—C8—C13—C12 | 175.72 (18) |
O1—S1—O3—C8 | −100.38 (15) | C9—C8—C13—C15 | −178.51 (19) |
C1—S1—O3—C8 | 145.53 (15) | O3—C8—C13—C15 | −1.9 (3) |
C17—N2—N3—C18 | −7.5 (2) | C11—C12—C13—C8 | 0.6 (3) |
C21—N2—N3—C18 | −159.44 (18) | C11—C12—C13—C15 | 178.3 (2) |
C17—N2—N3—C20 | −158.46 (19) | C16—N1—C15—C13 | −177.41 (17) |
C21—N2—N3—C20 | 49.6 (3) | C8—C13—C15—N1 | −165.84 (19) |
O2—S1—C1—C2 | 46.8 (2) | C12—C13—C15—N1 | 16.6 (3) |
O1—S1—C1—C2 | −179.9 (2) | C15—N1—C16—C18 | −170.18 (19) |
O3—S1—C1—C2 | −67.1 (2) | C15—N1—C16—C17 | 8.9 (3) |
O2—S1—C1—C6 | −130.3 (2) | N3—N2—C17—O5 | −174.35 (19) |
O1—S1—C1—C6 | 3.0 (2) | C21—N2—C17—O5 | −23.5 (3) |
O3—S1—C1—C6 | 115.8 (2) | N3—N2—C17—C16 | 5.0 (2) |
C6—C1—C2—C3 | 0.2 (4) | C21—N2—C17—C16 | 155.87 (19) |
S1—C1—C2—C3 | −176.9 (2) | C18—C16—C17—O5 | 178.4 (2) |
C1—C2—C3—C4 | −0.1 (5) | N1—C16—C17—O5 | −0.8 (4) |
C2—C3—C4—C5 | 0.2 (5) | C18—C16—C17—N2 | −0.9 (2) |
C2—C3—C4—C7 | −179.9 (3) | N1—C16—C17—N2 | 179.94 (19) |
C3—C4—C5—C6 | −0.4 (4) | N2—N3—C18—C16 | 6.9 (2) |
C7—C4—C5—C6 | 179.7 (3) | C20—N3—C18—C16 | 155.5 (2) |
C2—C1—C6—C5 | −0.4 (4) | N2—N3—C18—C19 | −171.31 (18) |
S1—C1—C6—C5 | 176.7 (2) | C20—N3—C18—C19 | −22.7 (3) |
C4—C5—C6—C1 | 0.5 (4) | N1—C16—C18—N3 | 175.48 (18) |
S1—O3—C8—C13 | 88.5 (2) | C17—C16—C18—N3 | −3.7 (2) |
S1—O3—C8—C9 | −94.75 (19) | N1—C16—C18—C19 | −6.5 (3) |
C14—O4—C9—C10 | −0.6 (3) | C17—C16—C18—C19 | 174.3 (2) |
C14—O4—C9—C8 | 179.9 (2) | C17—N2—C21—C22 | −112.6 (2) |
C13—C8—C9—O4 | −179.84 (19) | N3—N2—C21—C22 | 35.1 (3) |
O3—C8—C9—O4 | 3.5 (3) | C17—N2—C21—C26 | 65.5 (3) |
C13—C8—C9—C10 | 0.6 (3) | N3—N2—C21—C26 | −146.8 (2) |
O3—C8—C9—C10 | −176.11 (19) | C26—C21—C22—C23 | −0.4 (4) |
O4—C9—C10—C11 | −179.5 (2) | N2—C21—C22—C23 | 177.7 (2) |
C8—C9—C10—C11 | 0.0 (3) | C21—C22—C23—C24 | −1.1 (4) |
C9—C10—C11—C12 | −0.3 (4) | C22—C23—C24—C25 | 1.2 (5) |
C9—C10—C11—Cl1 | 178.83 (18) | C23—C24—C25—C26 | 0.0 (5) |
C10—C11—C12—C13 | −0.1 (4) | C24—C25—C26—C21 | −1.4 (5) |
Cl1—C11—C12—C13 | −179.15 (17) | C22—C21—C26—C25 | 1.6 (4) |
C9—C8—C13—C12 | −0.9 (3) | N2—C21—C26—C25 | −176.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2i | 0.93 | 2.57 | 3.386 (3) | 146 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H24ClN3O5S·C2H3N |
Mr | 567.06 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 7.3242 (9), 13.2452 (17), 15.3145 (19) |
α, β, γ (°) | 108.731 (2), 93.303 (2), 94.910 (2) |
V (Å3) | 1396.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.923, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7152, 4893, 4057 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.133, 1.02 |
No. of reflections | 4893 |
No. of parameters | 358 |
No. of restraints | 19 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.47 |
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 |
C10—H10···O2i | 0.93 | 2.57 | 3.386 (3) | 146 |
Symmetry code: (i) −x+1, −y, −z+1. |
Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986) in areas such as 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-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-ylimino)methyl]-phenyl 4-chlorobenzoate (Han et al., 2007) and (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Hu, 2006) have been reported. We now report the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)
The bond lengths and angles of (I) are within normal ranges (Allen et al., 1987). The pyrazolone ring (C16—C18/N1/N2/N3/O5) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.030 Å. It makes a dihedral angle of 54.45 (9)° with the attached phenyl ring (C21—C26). The o-vanillin group (C8—C13/C15/O3/O4) is almost planar, with an r.m.s. deviation for fitted atoms of 0.020 Å. This group makes dihedral angles of 25.87 (4)°, 11.93 (3)° and 72.05 (7)°, with the the pyrazolone ring (C16—C18/N1/N2/N3/O5), the terminal C1—C6 benzene ring and the terminal C21—C26 phenyl ring, respectively.
The crystal packing is stabilized by weak intermolecular C10—H10···O2═S1 interaction (Table 1, Fig. 2) that form inversion dimers.