organic compounds
(Z)-3-Methyl-1-phenyl-4-[(p-tolyl)(p-tolylamino)methylidene]-1H-pyrazol-5(4H)-one
aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Faculty of Science, The M. S. University of Baroda, Vadodara 390 002, India
*Correspondence e-mail: vivek_gupta2k2@hotmail.com
In the title molecule, C25H23N3O2, the pyrazole ring forms dihedral angles of 28.56 (7), 80.35 (7) and 31.99 (7)° with the phenyl ring, the p-tolyl ring and the p-tolylamino ring, respectively. The N—H group attached to the exocyclic C=C bond is in a syn arrangement with respect to the C=O bond of the pyrazolone group and an intramolecular N—H⋯O hydrogen bond is observed. In the crystal, weak C—H⋯π interactions link molecules along [100].
Related literature
For related structures, see: Vyas et al. (2011); Ma et al. (2006); Sun et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812040330/lh5535sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040330/lh5535Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812040330/lh5535Isup3.cml
Equimolar (10 mmol) ethanolic solution (50 ml) of 5-Methyl-4-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one and p-toluidine was refluxed for 6 h in round bottom flask, whereupon a microcrystalline yellow precipitate appeared. The product was then isolated and recrystallized from ethanol, and then dried in vacuo to give the title compound in 85% yield. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution of the title compound.
The H atom bonded to N was located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.96 Å and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C).
The title compound (I) was prepared as a continuation of our studies of the structures 4-toluoyl pyrazolones (Vyas et al., 2011). The molecular structure of (I) is shown in Fig 1. The bond lengths and angles in (I) are normal and correspond to those observed in related structures (Ma et al., 2006; Sun et al., 2007). The pyrazolone ring forms dihedral angles of 28.56 (7)°, 80.35 (7)° and 31.99 (7)° with the phenyl ring (C7—C12) and two benzene rings (C14—C19 and C22—C27). In The N—H group attached to the exocyclic C═C bond (C4-C13) is in a syn arrangement with respect to the C═O bond of the pyrazolone group and an intramolecular N—H···O hydrogen bond is observed. In the crystal, a weak C—H···π interaction link molecules along [100] (Fig .2).
For related structures, see: Vyas et al. (2011); Ma et al. (2006); Sun et al. (2007).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).C25H23N3O | F(000) = 808 |
Mr = 381.46 | Dx = 1.220 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3374 reflections |
a = 9.2694 (4) Å | θ = 3.5–29.0° |
b = 18.3156 (8) Å | µ = 0.08 mm−1 |
c = 12.6716 (7) Å | T = 293 K |
β = 105.124 (5)° | Block, yellow |
V = 2076.80 (17) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 4077 independent reflections |
Radiation source: fine-focus sealed tube | 2343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −22→19 |
Tmin = 0.914, Tmax = 1.000 | l = −15→12 |
9542 measured reflections |
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)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4077 reflections | Δρmax = 0.17 e Å−3 |
270 parameters | Δρmin = −0.14 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: 0.0018 (5) |
C25H23N3O | V = 2076.80 (17) Å3 |
Mr = 381.46 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2694 (4) Å | µ = 0.08 mm−1 |
b = 18.3156 (8) Å | T = 293 K |
c = 12.6716 (7) Å | 0.30 × 0.30 × 0.20 mm |
β = 105.124 (5)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 4077 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2343 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 1.000 | Rint = 0.039 |
9542 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.17 e Å−3 |
4077 reflections | Δρmin = −0.14 e Å−3 |
270 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | 0.37979 (16) | 0.27791 (8) | 0.08898 (14) | 0.0507 (5) | |
N2 | 0.34012 (18) | 0.35209 (9) | 0.07998 (16) | 0.0566 (5) | |
C3 | 0.1970 (2) | 0.35428 (11) | 0.03270 (17) | 0.0497 (6) | |
C4 | 0.1351 (2) | 0.28261 (10) | 0.01024 (16) | 0.0453 (5) | |
C5 | 0.2589 (2) | 0.23347 (11) | 0.04912 (16) | 0.0466 (5) | |
O5 | 0.26105 (14) | 0.16518 (7) | 0.04952 (12) | 0.0560 (4) | |
C6 | 0.1232 (2) | 0.42734 (11) | 0.0119 (2) | 0.0711 (8) | |
H6A | 0.1927 | 0.4645 | 0.0460 | 0.107* | |
H6B | 0.0380 | 0.4284 | 0.0416 | 0.107* | |
H6C | 0.0914 | 0.4361 | −0.0654 | 0.107* | |
C7 | 0.5268 (2) | 0.25907 (11) | 0.14877 (18) | 0.0489 (5) | |
C8 | 0.5900 (2) | 0.19386 (12) | 0.12908 (19) | 0.0588 (6) | |
H8 | 0.5369 | 0.1621 | 0.0757 | 0.071* | |
C9 | 0.7325 (2) | 0.17612 (13) | 0.1892 (2) | 0.0707 (7) | |
H9 | 0.7753 | 0.1322 | 0.1761 | 0.085* | |
C10 | 0.8117 (3) | 0.22272 (15) | 0.2681 (2) | 0.0741 (8) | |
H10 | 0.9072 | 0.2102 | 0.3089 | 0.089* | |
C11 | 0.7492 (2) | 0.28799 (14) | 0.28674 (19) | 0.0656 (7) | |
H11 | 0.8033 | 0.3198 | 0.3397 | 0.079* | |
C12 | 0.6064 (2) | 0.30674 (12) | 0.22733 (18) | 0.0562 (6) | |
H12 | 0.5644 | 0.3509 | 0.2401 | 0.067* | |
C13 | −0.0104 (2) | 0.25866 (11) | −0.03560 (16) | 0.0447 (5) | |
C14 | −0.1359 (2) | 0.31073 (10) | −0.07300 (16) | 0.0426 (5) | |
C15 | −0.2309 (2) | 0.32528 (11) | −0.00777 (18) | 0.0503 (6) | |
H15 | −0.2187 | 0.3008 | 0.0583 | 0.060* | |
C16 | −0.3446 (2) | 0.37642 (12) | −0.04055 (19) | 0.0574 (6) | |
H16 | −0.4067 | 0.3861 | 0.0047 | 0.069* | |
C17 | −0.3674 (2) | 0.41302 (11) | −0.1384 (2) | 0.0541 (6) | |
C18 | −0.2724 (2) | 0.39762 (12) | −0.20344 (18) | 0.0593 (6) | |
H18 | −0.2858 | 0.4217 | −0.2699 | 0.071* | |
C19 | −0.1579 (2) | 0.34719 (11) | −0.17182 (17) | 0.0555 (6) | |
H19 | −0.0956 | 0.3377 | −0.2170 | 0.067* | |
C20 | −0.4894 (2) | 0.46931 (12) | −0.1720 (2) | 0.0826 (9) | |
H20A | −0.5745 | 0.4544 | −0.1474 | 0.124* | |
H20B | −0.5176 | 0.4739 | −0.2502 | 0.124* | |
H20C | −0.4538 | 0.5155 | −0.1398 | 0.124* | |
N21 | −0.0338 (2) | 0.18632 (9) | −0.04121 (15) | 0.0546 (5) | |
C22 | −0.1653 (2) | 0.14481 (11) | −0.08416 (18) | 0.0503 (6) | |
C23 | −0.1729 (3) | 0.07733 (11) | −0.03820 (19) | 0.0636 (7) | |
H23 | −0.0940 | 0.0612 | 0.0186 | 0.076* | |
C24 | −0.2965 (3) | 0.03342 (13) | −0.0756 (2) | 0.0750 (8) | |
H24 | −0.2995 | −0.0122 | −0.0440 | 0.090* | |
C25 | −0.4156 (3) | 0.05601 (13) | −0.1591 (2) | 0.0666 (7) | |
C26 | −0.4042 (3) | 0.12227 (13) | −0.2062 (2) | 0.0676 (7) | |
H26 | −0.4824 | 0.1379 | −0.2639 | 0.081* | |
C27 | −0.2809 (2) | 0.16660 (12) | −0.17105 (19) | 0.0621 (7) | |
H27 | −0.2756 | 0.2109 | −0.2057 | 0.074* | |
C28 | −0.5540 (3) | 0.00866 (15) | −0.1984 (3) | 0.1072 (11) | |
H28A | −0.5999 | 0.0188 | −0.2741 | 0.161* | |
H28B | −0.6235 | 0.0192 | −0.1560 | 0.161* | |
H28C | −0.5261 | −0.0419 | −0.1900 | 0.161* | |
H21 | 0.060 (2) | 0.1594 (11) | −0.0076 (17) | 0.071 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0428 (9) | 0.0367 (10) | 0.0719 (12) | 0.0019 (8) | 0.0134 (8) | 0.0041 (9) |
N2 | 0.0461 (10) | 0.0386 (10) | 0.0830 (13) | 0.0030 (8) | 0.0129 (9) | 0.0032 (9) |
C3 | 0.0441 (11) | 0.0432 (13) | 0.0617 (14) | 0.0017 (10) | 0.0135 (10) | 0.0022 (11) |
C4 | 0.0409 (10) | 0.0384 (12) | 0.0571 (13) | 0.0009 (9) | 0.0136 (9) | 0.0017 (10) |
C5 | 0.0500 (12) | 0.0393 (13) | 0.0524 (13) | −0.0001 (10) | 0.0167 (10) | 0.0026 (11) |
O5 | 0.0573 (9) | 0.0382 (9) | 0.0702 (10) | 0.0036 (7) | 0.0126 (8) | 0.0043 (8) |
C6 | 0.0557 (13) | 0.0414 (13) | 0.107 (2) | 0.0041 (11) | 0.0059 (13) | 0.0020 (13) |
C7 | 0.0434 (11) | 0.0462 (13) | 0.0589 (14) | 0.0036 (10) | 0.0165 (10) | 0.0100 (11) |
C8 | 0.0518 (13) | 0.0508 (14) | 0.0747 (16) | 0.0046 (11) | 0.0183 (11) | 0.0078 (12) |
C9 | 0.0602 (15) | 0.0585 (16) | 0.093 (2) | 0.0177 (12) | 0.0189 (14) | 0.0180 (15) |
C10 | 0.0546 (14) | 0.0829 (19) | 0.0786 (19) | 0.0143 (14) | 0.0063 (13) | 0.0259 (16) |
C11 | 0.0580 (14) | 0.0756 (18) | 0.0593 (15) | −0.0034 (13) | 0.0084 (12) | 0.0096 (13) |
C12 | 0.0522 (12) | 0.0586 (15) | 0.0606 (14) | 0.0035 (11) | 0.0197 (11) | 0.0062 (12) |
C13 | 0.0487 (11) | 0.0385 (12) | 0.0502 (12) | 0.0021 (10) | 0.0187 (9) | 0.0016 (10) |
C14 | 0.0398 (10) | 0.0402 (12) | 0.0481 (12) | −0.0007 (9) | 0.0119 (9) | −0.0011 (10) |
C15 | 0.0489 (12) | 0.0503 (14) | 0.0540 (13) | −0.0028 (10) | 0.0174 (10) | 0.0030 (11) |
C16 | 0.0471 (12) | 0.0565 (14) | 0.0725 (16) | −0.0016 (11) | 0.0227 (11) | −0.0076 (13) |
C17 | 0.0439 (12) | 0.0397 (13) | 0.0700 (16) | −0.0004 (10) | −0.0006 (11) | −0.0071 (12) |
C18 | 0.0719 (15) | 0.0464 (14) | 0.0547 (14) | 0.0044 (12) | 0.0077 (12) | 0.0075 (12) |
C19 | 0.0662 (14) | 0.0516 (14) | 0.0529 (14) | 0.0054 (11) | 0.0228 (11) | 0.0029 (11) |
C20 | 0.0592 (15) | 0.0561 (15) | 0.116 (2) | 0.0091 (12) | −0.0072 (15) | −0.0108 (15) |
N21 | 0.0467 (10) | 0.0416 (11) | 0.0733 (13) | −0.0009 (9) | 0.0117 (9) | 0.0031 (10) |
C22 | 0.0532 (12) | 0.0380 (12) | 0.0631 (14) | −0.0033 (10) | 0.0211 (11) | −0.0037 (11) |
C23 | 0.0741 (15) | 0.0430 (14) | 0.0709 (16) | −0.0051 (12) | 0.0139 (13) | −0.0025 (12) |
C24 | 0.1014 (19) | 0.0424 (14) | 0.0863 (18) | −0.0170 (14) | 0.0338 (16) | −0.0045 (14) |
C25 | 0.0684 (15) | 0.0524 (15) | 0.0857 (18) | −0.0165 (13) | 0.0324 (14) | −0.0247 (14) |
C26 | 0.0591 (14) | 0.0579 (16) | 0.0823 (17) | −0.0048 (12) | 0.0120 (12) | −0.0122 (14) |
C27 | 0.0601 (14) | 0.0498 (14) | 0.0724 (16) | −0.0072 (11) | 0.0102 (12) | −0.0001 (12) |
C28 | 0.099 (2) | 0.089 (2) | 0.140 (3) | −0.0458 (17) | 0.0429 (19) | −0.038 (2) |
N1—C5 | 1.370 (2) | C15—H15 | 0.9300 |
N1—N2 | 1.404 (2) | C16—C17 | 1.377 (3) |
N1—C7 | 1.418 (2) | C16—H16 | 0.9300 |
N2—C3 | 1.306 (2) | C17—C18 | 1.383 (3) |
C3—C4 | 1.431 (3) | C17—C20 | 1.507 (3) |
C3—C6 | 1.495 (3) | C18—C19 | 1.385 (3) |
C4—C13 | 1.392 (2) | C18—H18 | 0.9300 |
C4—C5 | 1.440 (2) | C19—H19 | 0.9300 |
C5—O5 | 1.251 (2) | C20—H20A | 0.9600 |
C6—H6A | 0.9600 | C20—H20B | 0.9600 |
C6—H6B | 0.9600 | C20—H20C | 0.9600 |
C6—H6C | 0.9600 | N21—C22 | 1.419 (2) |
C7—C8 | 1.381 (3) | N21—H21 | 0.99 (2) |
C7—C12 | 1.384 (3) | C22—C23 | 1.376 (3) |
C8—C9 | 1.381 (3) | C22—C27 | 1.380 (3) |
C8—H8 | 0.9300 | C23—C24 | 1.378 (3) |
C9—C10 | 1.372 (3) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—C25 | 1.378 (3) |
C10—C11 | 1.375 (3) | C24—H24 | 0.9300 |
C10—H10 | 0.9300 | C25—C26 | 1.369 (3) |
C11—C12 | 1.384 (3) | C25—C28 | 1.521 (3) |
C11—H11 | 0.9300 | C26—C27 | 1.378 (3) |
C12—H12 | 0.9300 | C26—H26 | 0.9300 |
C13—N21 | 1.342 (2) | C27—H27 | 0.9300 |
C13—C14 | 1.483 (2) | C28—H28A | 0.9600 |
C14—C15 | 1.382 (3) | C28—H28B | 0.9600 |
C14—C19 | 1.386 (3) | C28—H28C | 0.9600 |
C15—C16 | 1.390 (3) | ||
C5—N1—N2 | 111.90 (14) | C17—C16—C15 | 121.6 (2) |
C5—N1—C7 | 129.18 (16) | C17—C16—H16 | 119.2 |
N2—N1—C7 | 118.26 (15) | C15—C16—H16 | 119.2 |
C3—N2—N1 | 106.27 (15) | C16—C17—C18 | 117.72 (19) |
N2—C3—C4 | 111.68 (17) | C16—C17—C20 | 121.0 (2) |
N2—C3—C6 | 118.15 (18) | C18—C17—C20 | 121.2 (2) |
C4—C3—C6 | 130.17 (17) | C17—C18—C19 | 121.5 (2) |
C13—C4—C3 | 131.76 (18) | C17—C18—H18 | 119.2 |
C13—C4—C5 | 122.98 (18) | C19—C18—H18 | 119.2 |
C3—C4—C5 | 105.24 (15) | C18—C19—C14 | 120.2 (2) |
O5—C5—N1 | 125.57 (16) | C18—C19—H19 | 119.9 |
O5—C5—C4 | 129.53 (17) | C14—C19—H19 | 119.9 |
N1—C5—C4 | 104.89 (16) | C17—C20—H20A | 109.5 |
C3—C6—H6A | 109.5 | C17—C20—H20B | 109.5 |
C3—C6—H6B | 109.5 | H20A—C20—H20B | 109.5 |
H6A—C6—H6B | 109.5 | C17—C20—H20C | 109.5 |
C3—C6—H6C | 109.5 | H20A—C20—H20C | 109.5 |
H6A—C6—H6C | 109.5 | H20B—C20—H20C | 109.5 |
H6B—C6—H6C | 109.5 | C13—N21—C22 | 131.33 (18) |
C8—C7—C12 | 120.25 (18) | C13—N21—H21 | 110.9 (11) |
C8—C7—N1 | 120.50 (19) | C22—N21—H21 | 117.8 (11) |
C12—C7—N1 | 119.25 (18) | C23—C22—C27 | 118.87 (19) |
C9—C8—C7 | 119.6 (2) | C23—C22—N21 | 116.91 (18) |
C9—C8—H8 | 120.2 | C27—C22—N21 | 124.16 (19) |
C7—C8—H8 | 120.2 | C22—C23—C24 | 120.5 (2) |
C10—C9—C8 | 120.5 (2) | C22—C23—H23 | 119.7 |
C10—C9—H9 | 119.7 | C24—C23—H23 | 119.7 |
C8—C9—H9 | 119.7 | C25—C24—C23 | 121.1 (2) |
C9—C10—C11 | 119.8 (2) | C25—C24—H24 | 119.5 |
C9—C10—H10 | 120.1 | C23—C24—H24 | 119.5 |
C11—C10—H10 | 120.1 | C26—C25—C24 | 117.6 (2) |
C10—C11—C12 | 120.5 (2) | C26—C25—C28 | 121.1 (2) |
C10—C11—H11 | 119.7 | C24—C25—C28 | 121.2 (2) |
C12—C11—H11 | 119.7 | C25—C26—C27 | 122.2 (2) |
C7—C12—C11 | 119.3 (2) | C25—C26—H26 | 118.9 |
C7—C12—H12 | 120.3 | C27—C26—H26 | 118.9 |
C11—C12—H12 | 120.3 | C26—C27—C22 | 119.6 (2) |
N21—C13—C4 | 117.32 (17) | C26—C27—H27 | 120.2 |
N21—C13—C14 | 121.02 (17) | C22—C27—H27 | 120.2 |
C4—C13—C14 | 121.62 (17) | C25—C28—H28A | 109.5 |
C15—C14—C19 | 118.75 (19) | C25—C28—H28B | 109.5 |
C15—C14—C13 | 120.14 (18) | H28A—C28—H28B | 109.5 |
C19—C14—C13 | 121.09 (19) | C25—C28—H28C | 109.5 |
C14—C15—C16 | 120.2 (2) | H28A—C28—H28C | 109.5 |
C14—C15—H15 | 119.9 | H28B—C28—H28C | 109.5 |
C16—C15—H15 | 119.9 | ||
C5—N1—N2—C3 | −1.5 (2) | C3—C4—C13—C14 | 0.8 (3) |
C7—N1—N2—C3 | −173.05 (18) | C5—C4—C13—C14 | 178.85 (19) |
N1—N2—C3—C4 | 1.1 (2) | N21—C13—C14—C15 | 77.8 (3) |
N1—N2—C3—C6 | −179.7 (2) | C4—C13—C14—C15 | −99.8 (2) |
N2—C3—C4—C13 | 178.0 (2) | N21—C13—C14—C19 | −104.0 (2) |
C6—C3—C4—C13 | −1.1 (4) | C4—C13—C14—C19 | 78.3 (3) |
N2—C3—C4—C5 | −0.4 (2) | C19—C14—C15—C16 | −1.0 (3) |
C6—C3—C4—C5 | −179.4 (2) | C13—C14—C15—C16 | 177.19 (17) |
N2—N1—C5—O5 | −178.0 (2) | C14—C15—C16—C17 | 0.9 (3) |
C7—N1—C5—O5 | −7.6 (4) | C15—C16—C17—C18 | −0.4 (3) |
N2—N1—C5—C4 | 1.2 (2) | C15—C16—C17—C20 | −178.89 (18) |
C7—N1—C5—C4 | 171.6 (2) | C16—C17—C18—C19 | 0.0 (3) |
C13—C4—C5—O5 | 0.1 (4) | C20—C17—C18—C19 | 178.46 (18) |
C3—C4—C5—O5 | 178.6 (2) | C17—C18—C19—C14 | −0.1 (3) |
C13—C4—C5—N1 | −179.07 (19) | C15—C14—C19—C18 | 0.6 (3) |
C3—C4—C5—N1 | −0.5 (2) | C13—C14—C19—C18 | −177.60 (18) |
C5—N1—C7—C8 | 33.6 (3) | C4—C13—N21—C22 | −178.6 (2) |
N2—N1—C7—C8 | −156.5 (2) | C14—C13—N21—C22 | 3.6 (4) |
C5—N1—C7—C12 | −146.3 (2) | C13—N21—C22—C23 | −152.0 (2) |
N2—N1—C7—C12 | 23.6 (3) | C13—N21—C22—C27 | 30.9 (4) |
C12—C7—C8—C9 | 0.8 (3) | C27—C22—C23—C24 | −2.4 (4) |
N1—C7—C8—C9 | −179.15 (19) | N21—C22—C23—C24 | −179.6 (2) |
C7—C8—C9—C10 | 0.0 (4) | C22—C23—C24—C25 | −0.5 (4) |
C8—C9—C10—C11 | −0.7 (4) | C23—C24—C25—C26 | 2.5 (4) |
C9—C10—C11—C12 | 0.7 (4) | C23—C24—C25—C28 | −178.2 (2) |
C8—C7—C12—C11 | −0.7 (3) | C24—C25—C26—C27 | −1.6 (4) |
N1—C7—C12—C11 | 179.17 (19) | C28—C25—C26—C27 | 179.1 (2) |
C10—C11—C12—C7 | 0.0 (3) | C25—C26—C27—C22 | −1.3 (4) |
C3—C4—C13—N21 | −176.9 (2) | C23—C22—C27—C26 | 3.3 (4) |
C5—C4—C13—N21 | 1.2 (3) | N21—C22—C27—C26 | −179.7 (2) |
Cg is the centroid of the C7–C12 ring |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O5 | 0.99 (2) | 1.82 (2) | 2.702 (2) | 146.4 (17) |
C15—H15···Cgi | 0.93 | 2.63 | 3.470 (2) | 152 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C25H23N3O |
Mr | 381.46 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 9.2694 (4), 18.3156 (8), 12.6716 (7) |
β (°) | 105.124 (5) |
V (Å3) | 2076.80 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.914, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9542, 4077, 2343 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.132, 1.01 |
No. of reflections | 4077 |
No. of parameters | 270 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.14 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
Cg is the centroid of the C7–C12 ring |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O5 | 0.99 (2) | 1.82 (2) | 2.702 (2) | 146.4 (17) |
C15—H15···Cgi | 0.93 | 2.63 | 3.470 (2) | 152 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. VKG is thankful to the University of Jammu, Jammu, for financial support.
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ma, R.-M., Sun, S.-F. & Ng, S. W. (2006). Acta Cryst. E62, o4679–o4680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-F., Li, J.-K., Wu, R.-T. & Zheng, Z.-B. (2007). Acta Cryst. E63, o2176–o2177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vyas, K. M., Jadeja, R. N., Gupta, V. K. & Surati, K. R. (2011). J. Mol. Struct. 990, 110–120. Web of Science CSD CrossRef CAS Google Scholar
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The title compound (I) was prepared as a continuation of our studies of the structures 4-toluoyl pyrazolones (Vyas et al., 2011). The molecular structure of (I) is shown in Fig 1. The bond lengths and angles in (I) are normal and correspond to those observed in related structures (Ma et al., 2006; Sun et al., 2007). The pyrazolone ring forms dihedral angles of 28.56 (7)°, 80.35 (7)° and 31.99 (7)° with the phenyl ring (C7—C12) and two benzene rings (C14—C19 and C22—C27). In The N—H group attached to the exocyclic C═C bond (C4-C13) is in a syn arrangement with respect to the C═O bond of the pyrazolone group and an intramolecular N—H···O hydrogen bond is observed. In the crystal, a weak C—H···π interaction link molecules along [100] (Fig .2).