organic compounds
4-({4-[1-(Methoxyimino)ethyl]anilino}(phenyl)methylene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one
aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and bSchool of Environmental Science and Municipal Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: dongwk@126.com
In the title compound, C26H24N4O2, the dihedral angles between the central pyrazole ring and the other three benzene rings are 40.02 (3), 77.51 (5) and 55.72 (3)°. A strong intramolecular N—H⋯O hydrogen bond forms a six-membered ring with an S(6) motif. In the a weak intermolecular C—H⋯N interaction with graph-set motif R22(8) and C—H⋯O hydrogen bonds link each molecule to three others, forming an infinite two-dimensional supramolecular structure.
Related literature
For background to 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, see: Lahiri et al. (2003). For related structures, see: Bomfim et al. (2005); Wang et al. (2008). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For the synthesis, see: Rafiq et al. (2008); Zhao et al. (2009); Dong et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809048326/fl2280sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809048326/fl2280Isup2.hkl
1-(4-Aminophenyl)ethanone O-methyl oxime (I) was prepared using 1-(4-aminophenyl)ethanone and methoxyamine (Rafiq et al., 2008; Zhao et al., 2009). The title compound was prepared according to a previously reported procedure (Dong et al., 2008). To an ethanol solution (7 ml) of (I) (164.1 mg, 1.00 mmol) was added dropwise an ethanol solution (7 ml) of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (278.3 mg,1.00 mmol). The mixture was stirred at 333–338 K for 24 h. The solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound. Yield, 68.9%. m. p. 454–456 K. Anal. Calcd. for C26H24N4O2: C, 73.56; H, 5.70; N, 13.20. Found: C,73.63; H,5.81; N,13.07.
Pale-yellow block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of dichloromethane at room temperature over a period of approximately one month.
H atoms were placed in calculated positions and non-H atoms were refined anisotropically. The remaining H atoms were treated as riding atoms with distances C—H=0.96 Å (CH3), 0.93 Å (CH), 0.86 Å (NH), while Uiso(H)=1.20 Ueq(C) for methylidyne and 1.20 Ueq(N) for imino, 1.50 Ueq(C) for methyl. The H atom attached to N atom was located in a different density map and the atomic coordinates allowed to refine freely.
Data collection: SMART (Siemens, 1996); cell
SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C26H24N4O2 | Z = 2 |
Mr = 424.49 | F(000) = 448 |
Triclinic, P1 | Dx = 1.286 Mg m−3 |
Hall symbol: -P 1 | Melting point = 454–456 K |
a = 7.3550 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1609 (13) Å | Cell parameters from 1018 reflections |
c = 14.9700 (12) Å | θ = 2.9–22.3° |
α = 68.536 (1)° | µ = 0.08 mm−1 |
β = 76.654 (2)° | T = 298 K |
γ = 76.182 (2)° | Block-like, yellow |
V = 1096.46 (18) Å3 | 0.50 × 0.49 × 0.10 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 3781 independent reflections |
Radiation source: fine-focus sealed tube | 1861 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
phi and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.960, Tmax = 0.992 | k = −13→13 |
5654 measured reflections | l = −12→17 |
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)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.246 | w = 1/[σ2(Fo2) + (0.1078P)2 + 0.3814P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3781 reflections | Δρmax = 0.24 e Å−3 |
290 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (5) |
C26H24N4O2 | γ = 76.182 (2)° |
Mr = 424.49 | V = 1096.46 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3550 (6) Å | Mo Kα radiation |
b = 11.1609 (13) Å | µ = 0.08 mm−1 |
c = 14.9700 (12) Å | T = 298 K |
α = 68.536 (1)° | 0.50 × 0.49 × 0.10 mm |
β = 76.654 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3781 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1861 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.992 | Rint = 0.037 |
5654 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.246 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
3781 reflections | Δρmin = −0.26 e Å−3 |
290 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 | ||
N1 | 0.5909 (5) | 0.6071 (3) | 0.1299 (3) | 0.0443 (10) | |
N2 | 0.6863 (5) | 0.5101 (4) | 0.0891 (3) | 0.0476 (10) | |
N3 | 0.1377 (5) | 0.4355 (4) | 0.2977 (3) | 0.0498 (11) | |
H3 | 0.1605 | 0.5047 | 0.3025 | 0.060* | |
N4 | −0.5909 (6) | 0.1833 (5) | 0.5239 (3) | 0.0646 (13) | |
O1 | 0.3193 (4) | 0.6395 (3) | 0.2404 (2) | 0.0505 (9) | |
O2 | −0.7474 (6) | 0.1375 (4) | 0.5927 (3) | 0.0817 (13) | |
C1 | 0.4246 (6) | 0.5767 (4) | 0.1894 (3) | 0.0403 (11) | |
C2 | 0.4103 (6) | 0.4552 (4) | 0.1810 (3) | 0.0384 (11) | |
C3 | 0.5784 (7) | 0.4221 (4) | 0.1177 (3) | 0.0449 (12) | |
C4 | 0.6428 (7) | 0.3052 (5) | 0.0868 (4) | 0.0602 (15) | |
H4A | 0.7660 | 0.3094 | 0.0477 | 0.090* | |
H4B | 0.5548 | 0.3022 | 0.0495 | 0.090* | |
H4C | 0.6494 | 0.2281 | 0.1431 | 0.090* | |
C5 | 0.6829 (6) | 0.7119 (4) | 0.1179 (3) | 0.0406 (11) | |
C6 | 0.5761 (7) | 0.8342 (5) | 0.1089 (4) | 0.0532 (13) | |
H6 | 0.4470 | 0.8489 | 0.1069 | 0.064* | |
C7 | 0.6606 (8) | 0.9334 (5) | 0.1030 (4) | 0.0600 (15) | |
H7 | 0.5880 | 1.0155 | 0.0983 | 0.072* | |
C8 | 0.8494 (8) | 0.9141 (6) | 0.1040 (4) | 0.0665 (16) | |
H8 | 0.9060 | 0.9825 | 0.0998 | 0.080* | |
C9 | 0.9571 (7) | 0.7925 (6) | 0.1112 (4) | 0.0654 (16) | |
H9 | 1.0869 | 0.7792 | 0.1111 | 0.078* | |
C10 | 0.8737 (7) | 0.6911 (5) | 0.1184 (4) | 0.0533 (14) | |
H10 | 0.9461 | 0.6089 | 0.1237 | 0.064* | |
C11 | 0.2609 (6) | 0.3874 (4) | 0.2346 (3) | 0.0401 (11) | |
C12 | 0.2423 (6) | 0.2628 (4) | 0.2279 (3) | 0.0422 (12) | |
C13 | 0.2792 (7) | 0.1492 (5) | 0.3045 (4) | 0.0532 (13) | |
H13 | 0.3171 | 0.1517 | 0.3588 | 0.064* | |
C14 | 0.2592 (7) | 0.0319 (5) | 0.2996 (4) | 0.0610 (15) | |
H14 | 0.2862 | −0.0447 | 0.3506 | 0.073* | |
C15 | 0.2010 (7) | 0.0263 (5) | 0.2221 (4) | 0.0613 (15) | |
H15 | 0.1853 | −0.0529 | 0.2202 | 0.074* | |
C16 | 0.1653 (7) | 0.1410 (5) | 0.1456 (4) | 0.0598 (15) | |
H16 | 0.1251 | 0.1385 | 0.0919 | 0.072* | |
C17 | 0.1881 (6) | 0.2558 (5) | 0.1483 (4) | 0.0500 (13) | |
H17 | 0.1668 | 0.3313 | 0.0955 | 0.060* | |
C18 | −0.0273 (6) | 0.3889 (4) | 0.3586 (3) | 0.0408 (11) | |
C19 | −0.0580 (7) | 0.3782 (5) | 0.4543 (4) | 0.0500 (13) | |
H19 | 0.0328 | 0.3967 | 0.4792 | 0.060* | |
C20 | −0.2214 (6) | 0.3404 (4) | 0.5147 (4) | 0.0488 (13) | |
H20 | −0.2408 | 0.3350 | 0.5796 | 0.059* | |
C21 | −0.3560 (6) | 0.3105 (4) | 0.4794 (3) | 0.0426 (12) | |
C22 | −0.3236 (6) | 0.3217 (4) | 0.3821 (3) | 0.0448 (12) | |
H22 | −0.4128 | 0.3012 | 0.3574 | 0.054* | |
C23 | −0.1635 (6) | 0.3622 (4) | 0.3211 (4) | 0.0467 (12) | |
H23 | −0.1463 | 0.3717 | 0.2555 | 0.056* | |
C24 | −0.5294 (6) | 0.2642 (4) | 0.5452 (4) | 0.0460 (12) | |
C25 | −0.6082 (7) | 0.3043 (6) | 0.6314 (4) | 0.0646 (15) | |
H25A | −0.7391 | 0.2944 | 0.6510 | 0.097* | |
H25B | −0.5983 | 0.3941 | 0.6161 | 0.097* | |
H25C | −0.5387 | 0.2506 | 0.6833 | 0.097* | |
C26 | −0.7905 (10) | 0.0306 (7) | 0.5759 (6) | 0.111 (3) | |
H26A | −0.8927 | 0.0611 | 0.5388 | 0.166* | |
H26B | −0.8271 | −0.0336 | 0.6370 | 0.166* | |
H26C | −0.6806 | −0.0079 | 0.5404 | 0.166* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.051 (2) | 0.042 (2) | 0.044 (2) | −0.0190 (19) | 0.000 (2) | −0.0154 (19) |
N2 | 0.050 (2) | 0.053 (2) | 0.041 (3) | −0.017 (2) | 0.002 (2) | −0.017 (2) |
N3 | 0.051 (2) | 0.051 (2) | 0.054 (3) | −0.027 (2) | 0.005 (2) | −0.021 (2) |
N4 | 0.053 (3) | 0.090 (3) | 0.056 (3) | −0.038 (2) | 0.022 (2) | −0.031 (3) |
O1 | 0.048 (2) | 0.055 (2) | 0.054 (2) | −0.0193 (16) | 0.0039 (17) | −0.0249 (18) |
O2 | 0.076 (3) | 0.091 (3) | 0.077 (3) | −0.041 (2) | 0.017 (2) | −0.028 (2) |
C1 | 0.043 (3) | 0.051 (3) | 0.032 (3) | −0.019 (2) | −0.005 (2) | −0.014 (2) |
C2 | 0.043 (3) | 0.043 (3) | 0.031 (3) | −0.017 (2) | −0.002 (2) | −0.011 (2) |
C3 | 0.051 (3) | 0.050 (3) | 0.039 (3) | −0.018 (2) | −0.005 (2) | −0.015 (2) |
C4 | 0.060 (3) | 0.059 (3) | 0.067 (4) | −0.020 (3) | 0.004 (3) | −0.029 (3) |
C5 | 0.042 (3) | 0.044 (3) | 0.035 (3) | −0.017 (2) | 0.000 (2) | −0.008 (2) |
C6 | 0.046 (3) | 0.056 (3) | 0.056 (3) | −0.019 (3) | 0.001 (3) | −0.015 (3) |
C7 | 0.064 (4) | 0.056 (3) | 0.061 (4) | −0.024 (3) | 0.012 (3) | −0.025 (3) |
C8 | 0.077 (4) | 0.074 (4) | 0.062 (4) | −0.045 (3) | 0.002 (3) | −0.025 (3) |
C9 | 0.047 (3) | 0.078 (4) | 0.071 (4) | −0.029 (3) | −0.007 (3) | −0.014 (3) |
C10 | 0.045 (3) | 0.050 (3) | 0.060 (4) | −0.014 (2) | −0.011 (3) | −0.006 (3) |
C11 | 0.048 (3) | 0.041 (3) | 0.035 (3) | −0.007 (2) | −0.012 (2) | −0.014 (2) |
C12 | 0.043 (3) | 0.047 (3) | 0.039 (3) | −0.018 (2) | −0.004 (2) | −0.011 (2) |
C13 | 0.057 (3) | 0.053 (3) | 0.048 (3) | −0.009 (2) | −0.019 (3) | −0.009 (3) |
C14 | 0.072 (4) | 0.038 (3) | 0.064 (4) | −0.010 (3) | −0.017 (3) | −0.004 (3) |
C15 | 0.064 (3) | 0.057 (3) | 0.067 (4) | −0.026 (3) | 0.010 (3) | −0.028 (3) |
C16 | 0.072 (4) | 0.072 (4) | 0.053 (4) | −0.036 (3) | 0.001 (3) | −0.033 (3) |
C17 | 0.057 (3) | 0.057 (3) | 0.039 (3) | −0.021 (2) | −0.005 (2) | −0.013 (2) |
C18 | 0.048 (3) | 0.037 (2) | 0.041 (3) | −0.018 (2) | −0.002 (2) | −0.013 (2) |
C19 | 0.054 (3) | 0.062 (3) | 0.045 (3) | −0.022 (3) | −0.007 (3) | −0.024 (3) |
C20 | 0.054 (3) | 0.058 (3) | 0.038 (3) | −0.018 (2) | −0.002 (2) | −0.018 (2) |
C21 | 0.049 (3) | 0.036 (2) | 0.039 (3) | −0.010 (2) | −0.006 (2) | −0.008 (2) |
C22 | 0.049 (3) | 0.051 (3) | 0.039 (3) | −0.020 (2) | −0.007 (2) | −0.013 (2) |
C23 | 0.055 (3) | 0.056 (3) | 0.033 (3) | −0.018 (2) | −0.008 (2) | −0.013 (2) |
C24 | 0.051 (3) | 0.045 (3) | 0.039 (3) | −0.012 (2) | −0.005 (2) | −0.009 (2) |
C25 | 0.065 (4) | 0.077 (4) | 0.047 (4) | −0.016 (3) | 0.001 (3) | −0.018 (3) |
C26 | 0.113 (6) | 0.106 (5) | 0.127 (7) | −0.073 (5) | 0.034 (5) | −0.052 (5) |
N1—C1 | 1.371 (5) | C12—C17 | 1.374 (6) |
N1—N2 | 1.401 (5) | C12—C13 | 1.383 (6) |
N1—C5 | 1.424 (5) | C13—C14 | 1.381 (7) |
N2—C3 | 1.298 (5) | C13—H13 | 0.9300 |
N3—C11 | 1.321 (6) | C14—C15 | 1.352 (8) |
N3—C18 | 1.421 (5) | C14—H14 | 0.9300 |
N3—H3 | 0.8600 | C15—C16 | 1.387 (7) |
N4—C24 | 1.263 (6) | C15—H15 | 0.9300 |
N4—O2 | 1.412 (5) | C16—C17 | 1.348 (6) |
O1—C1 | 1.239 (5) | C16—H16 | 0.9300 |
O2—C26 | 1.423 (7) | C17—H17 | 0.9300 |
C1—C2 | 1.436 (6) | C18—C19 | 1.361 (6) |
C2—C11 | 1.403 (6) | C18—C23 | 1.390 (6) |
C2—C3 | 1.435 (6) | C19—C20 | 1.379 (6) |
C3—C4 | 1.479 (7) | C19—H19 | 0.9300 |
C4—H4A | 0.9600 | C20—C21 | 1.378 (6) |
C4—H4B | 0.9600 | C20—H20 | 0.9300 |
C4—H4C | 0.9600 | C21—C22 | 1.383 (6) |
C5—C10 | 1.368 (6) | C21—C24 | 1.492 (6) |
C5—C6 | 1.379 (6) | C22—C23 | 1.371 (6) |
C6—C7 | 1.360 (6) | C22—H22 | 0.9300 |
C6—H6 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.356 (7) | C24—C25 | 1.467 (7) |
C7—H7 | 0.9300 | C25—H25A | 0.9600 |
C8—C9 | 1.378 (8) | C25—H25B | 0.9600 |
C8—H8 | 0.9300 | C25—H25C | 0.9600 |
C9—C10 | 1.371 (7) | C26—H26A | 0.9600 |
C9—H9 | 0.9300 | C26—H26B | 0.9600 |
C10—H10 | 0.9300 | C26—H26C | 0.9600 |
C11—C12 | 1.470 (6) | ||
C1—N1—N2 | 112.5 (3) | C14—C13—C12 | 119.4 (5) |
C1—N1—C5 | 127.5 (4) | C14—C13—H13 | 120.3 |
N2—N1—C5 | 119.3 (4) | C12—C13—H13 | 120.3 |
C3—N2—N1 | 106.5 (4) | C15—C14—C13 | 121.3 (5) |
C11—N3—C18 | 129.1 (4) | C15—C14—H14 | 119.4 |
C11—N3—H3 | 115.4 | C13—C14—H14 | 119.4 |
C18—N3—H3 | 115.4 | C14—C15—C16 | 118.7 (5) |
C24—N4—O2 | 111.5 (4) | C14—C15—H15 | 120.6 |
N4—O2—C26 | 109.4 (5) | C16—C15—H15 | 120.6 |
O1—C1—N1 | 126.3 (4) | C17—C16—C15 | 120.8 (5) |
O1—C1—C2 | 129.8 (4) | C17—C16—H16 | 119.6 |
N1—C1—C2 | 103.8 (4) | C15—C16—H16 | 119.6 |
C11—C2—C3 | 131.8 (4) | C16—C17—C12 | 120.8 (5) |
C11—C2—C1 | 121.9 (4) | C16—C17—H17 | 119.6 |
C3—C2—C1 | 106.1 (4) | C12—C17—H17 | 119.6 |
N2—C3—C2 | 111.0 (4) | C19—C18—C23 | 119.5 (4) |
N2—C3—C4 | 119.2 (4) | C19—C18—N3 | 119.2 (4) |
C2—C3—C4 | 129.8 (4) | C23—C18—N3 | 121.2 (4) |
C3—C4—H4A | 109.5 | C18—C19—C20 | 121.1 (4) |
C3—C4—H4B | 109.5 | C18—C19—H19 | 119.5 |
H4A—C4—H4B | 109.5 | C20—C19—H19 | 119.5 |
C3—C4—H4C | 109.5 | C21—C20—C19 | 120.3 (5) |
H4A—C4—H4C | 109.5 | C21—C20—H20 | 119.9 |
H4B—C4—H4C | 109.5 | C19—C20—H20 | 119.9 |
C10—C5—C6 | 120.2 (4) | C20—C21—C22 | 118.2 (4) |
C10—C5—N1 | 120.6 (4) | C20—C21—C24 | 120.6 (4) |
C6—C5—N1 | 119.1 (4) | C22—C21—C24 | 121.1 (4) |
C7—C6—C5 | 119.7 (5) | C23—C22—C21 | 121.8 (4) |
C7—C6—H6 | 120.2 | C23—C22—H22 | 119.1 |
C5—C6—H6 | 120.2 | C21—C22—H22 | 119.1 |
C8—C7—C6 | 120.8 (5) | C22—C23—C18 | 119.1 (4) |
C8—C7—H7 | 119.6 | C22—C23—H23 | 120.4 |
C6—C7—H7 | 119.6 | C18—C23—H23 | 120.4 |
C7—C8—C9 | 119.6 (5) | N4—C24—C25 | 124.5 (4) |
C7—C8—H8 | 120.2 | N4—C24—C21 | 114.6 (4) |
C9—C8—H8 | 120.2 | C25—C24—C21 | 120.7 (4) |
C10—C9—C8 | 120.3 (5) | C24—C25—H25A | 109.5 |
C10—C9—H9 | 119.9 | C24—C25—H25B | 109.5 |
C8—C9—H9 | 119.9 | H25A—C25—H25B | 109.5 |
C5—C10—C9 | 119.4 (5) | C24—C25—H25C | 109.5 |
C5—C10—H10 | 120.3 | H25A—C25—H25C | 109.5 |
C9—C10—H10 | 120.3 | H25B—C25—H25C | 109.5 |
N3—C11—C2 | 117.6 (4) | O2—C26—H26A | 109.5 |
N3—C11—C12 | 119.0 (4) | O2—C26—H26B | 109.5 |
C2—C11—C12 | 123.3 (4) | H26A—C26—H26B | 109.5 |
C17—C12—C13 | 119.0 (4) | O2—C26—H26C | 109.5 |
C17—C12—C11 | 122.1 (4) | H26A—C26—H26C | 109.5 |
C13—C12—C11 | 118.9 (4) | H26B—C26—H26C | 109.5 |
C1—N1—N2—C3 | 3.3 (5) | C3—C2—C11—C12 | −5.7 (7) |
C5—N1—N2—C3 | 174.7 (4) | C1—C2—C11—C12 | −179.8 (4) |
C24—N4—O2—C26 | −169.8 (5) | N3—C11—C12—C17 | 110.5 (5) |
N2—N1—C1—O1 | 174.2 (4) | C2—C11—C12—C17 | −73.3 (6) |
C5—N1—C1—O1 | 3.7 (7) | N3—C11—C12—C13 | −69.0 (6) |
N2—N1—C1—C2 | −3.2 (5) | C2—C11—C12—C13 | 107.2 (5) |
C5—N1—C1—C2 | −173.8 (4) | C17—C12—C13—C14 | −0.6 (7) |
O1—C1—C2—C11 | 0.1 (7) | C11—C12—C13—C14 | 179.0 (4) |
N1—C1—C2—C11 | 177.4 (4) | C12—C13—C14—C15 | −1.2 (8) |
O1—C1—C2—C3 | −175.3 (5) | C13—C14—C15—C16 | 1.4 (8) |
N1—C1—C2—C3 | 1.9 (5) | C14—C15—C16—C17 | 0.0 (8) |
N1—N2—C3—C2 | −1.8 (5) | C15—C16—C17—C12 | −1.8 (8) |
N1—N2—C3—C4 | −179.4 (4) | C13—C12—C17—C16 | 2.0 (7) |
C11—C2—C3—N2 | −174.9 (4) | C11—C12—C17—C16 | −177.5 (4) |
C1—C2—C3—N2 | −0.1 (5) | C11—N3—C18—C19 | 132.8 (5) |
C11—C2—C3—C4 | 2.3 (8) | C11—N3—C18—C23 | −51.4 (7) |
C1—C2—C3—C4 | 177.1 (5) | C23—C18—C19—C20 | 0.5 (7) |
C1—N1—C5—C10 | 133.8 (5) | N3—C18—C19—C20 | 176.3 (4) |
N2—N1—C5—C10 | −36.2 (6) | C18—C19—C20—C21 | 1.1 (7) |
C1—N1—C5—C6 | −44.1 (7) | C19—C20—C21—C22 | −1.1 (7) |
N2—N1—C5—C6 | 145.9 (4) | C19—C20—C21—C24 | 177.4 (4) |
C10—C5—C6—C7 | −1.6 (8) | C20—C21—C22—C23 | −0.5 (7) |
N1—C5—C6—C7 | 176.2 (5) | C24—C21—C22—C23 | −179.0 (4) |
C5—C6—C7—C8 | 1.3 (8) | C21—C22—C23—C18 | 2.0 (7) |
C6—C7—C8—C9 | −0.1 (9) | C19—C18—C23—C22 | −2.0 (7) |
C7—C8—C9—C10 | −0.7 (9) | N3—C18—C23—C22 | −177.8 (4) |
C6—C5—C10—C9 | 0.8 (8) | O2—N4—C24—C25 | 0.9 (7) |
N1—C5—C10—C9 | −177.0 (5) | O2—N4—C24—C21 | 176.2 (4) |
C8—C9—C10—C5 | 0.4 (9) | C20—C21—C24—N4 | −146.8 (5) |
C18—N3—C11—C2 | 178.2 (4) | C22—C21—C24—N4 | 31.6 (7) |
C18—N3—C11—C12 | −5.4 (7) | C20—C21—C24—C25 | 28.7 (7) |
C3—C2—C11—N3 | 170.6 (5) | C22—C21—C24—C25 | −152.9 (5) |
C1—C2—C11—N3 | −3.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1 | 0.86 | 1.95 | 2.683 (4) | 142 |
C26—H26C···N4i | 0.96 | 2.72 | 3.643 (9) | 163 |
C9—H9···O1ii | 0.93 | 2.67 | 3.398 (6) | 135 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C26H24N4O2 |
Mr | 424.49 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.3550 (6), 11.1609 (13), 14.9700 (12) |
α, β, γ (°) | 68.536 (1), 76.654 (2), 76.182 (2) |
V (Å3) | 1096.46 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.49 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.960, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5654, 3781, 1861 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.246, 1.03 |
No. of reflections | 3781 |
No. of parameters | 290 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.26 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1 | 0.86 | 1.95 | 2.683 (4) | 142.3 |
C26—H26C···N4i | 0.96 | 2.72 | 3.643 (9) | 162.8 |
C9—H9···O1ii | 0.93 | 2.67 | 3.398 (6) | 135.3 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) x+1, y, z. |
Acknowledgements
This work was supported by the Foundation of the Education Department of Gansu Province (0904–11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) is an efficient extractant of metal ions, and has the potential to form different types of compounds (Lahiri et al., 2003). Some structures of oxime compounds, similar to the title compound (Fig. 1), formed by Schiff base reactions have been reported (Bomfim et al., 2005; Wang et al., 2008).
The title compound is a potential tridentate mono-oxime ligand. The bond lengths and angles in the molecule are within normal ranges (Allen et al., 1987). In the molecule, the dihedral angles between the central pyrazole ring and the other three benzene rings (C5—C10), (C12—C17) and (C18—C23) are 40.02 (3)°, 77.51 (5)° and 55.72 (3)°, respectively.
In the crystal, a strong intramolecular N3—H3···O1 hydrogen bond forms a six-membered ring, producing a S(6) ring motif (Table 1, Fig. 1). A weak intermolecular C26—H26C···N4 interacation with the graph-set motif of R22(8) (Bernstein et al., 1995) and C9—H9···O1 hydrogen bonds, link each molecule to three others, forming an infinite two-dimensional supramolecular structure along the diagonal of the unit cell (Table 1, Fig. 2).