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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jan 11;68(Pt 2):o352. doi: 10.1107/S1600536812000402

N′-[(Z)-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyl­idene]-2-hy­droxy­benzohydrazide

Muhammad Aslam a,b,*, Itrat Anis b, Nighat Afza a, Ejaz c, Islam Ullah Khan c, Muhammad Nadeem Arshad d,*
PMCID: PMC3275035  PMID: 22346980

Abstract

In the title compound, C19H18N4O3, the pyrazole ring is oriented at dihedral angles of 41.12 (7) and 12.25 (10)°, respectively, with respect to the planes of the phenyl and benzene rings. Intra­molecular N—H⋯O and O—H⋯O hydrogen bonds generate seven- and six-membered S(7) and S(6) ring motifs, respectively.

Related literature

For the biological activity of Schiff bases, see: Lau et al. (1999 ▶); More et al. (2002 ▶); Safwat et al. (1988 ▶); Sharma et al. (1998 ▶); Pandeya et al. (1999 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).graphic file with name e-68-0o352-scheme1.jpg

Experimental

Crystal data

  • C19H18N4O3

  • M r = 350.37

  • Monoclinic, Inline graphic

  • a = 25.2357 (6) Å

  • b = 8.5624 (2) Å

  • c = 16.0329 (4) Å

  • β = 104.048 (1)°

  • V = 3360.75 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.22 × 0.06 × 0.05 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.980, T max = 0.995

  • 16063 measured reflections

  • 4174 independent reflections

  • 2653 reflections with I > 2σ(I)

  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.119

  • S = 1.02

  • 4174 reflections

  • 243 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000402/is5039sup1.cif

e-68-0o352-sup1.cif (27.2KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000402/is5039Isup2.hkl

e-68-0o352-Isup2.hkl (204.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812000402/is5039Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3O⋯O2 0.95 (2) 1.62 (2) 2.5076 (17) 155 (2)
N4—H4N⋯O1 0.978 (18) 1.763 (18) 2.7140 (16) 163.3 (16)
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Acknowledgments

MA expresses his gratitude to the Pakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi, the Department of Chemistry, University of Karachi, and the Department of Chemistry, Govt. College University Lahore, for providing financial support, research facilities and X-ray diffraction facilities, respectively.

supplementary crystallographic information

Comment

The Schiff base ligands have importance for elucidating the mechanism of racemization and transamination reactions in biological systems (Lau et al., 1999) and exhibit remarkable biological activities such as antibacterial (More et al., 2002), antifungal (Safwat et al., 1988), anticancer (Sharma et al., 1998) and anti HIV activities (Pandeya et al., 1999). Such applications lead us to report the synthesis and characterization of Schiff base ligand, N'-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) methylene)-2-hydroxybenzohydrazide.

In the crystal structure of title compound, two nitrogen and three carbon atoms of pyrazole ring are sp2 hybridized, whose ring shows an r.m.s. deviation of about 0.1 Å with the maximum deviation of from N1 [0.1256 (12) Å] and C8 [0.1237 (10) Å]. The molecule contains N—H and O—H groups but no classical intermolecular hydrogen bonding has been observed. Only intramolecular hydrogen bonding produces six-membered S(6) and seven-membered S(7) (Bernstein et al., 1995) ring motifs through O—H···O and N—H···O interactions (Table 1 and Fig. 1). The two ring motifs O1/C7/C8/C10/N3/N4/H4N and O2/C11/C12/C13/O3/H3O are inclined at a dihedral angle of 3.46 (4)°. The phenyl ring (C1–C6) is twisted at 41.12 (7) and 41.64 (7)°, respectively, with the pyrazole ring and o-hydroxy benzoyl ring (C12–C17).

Experimental

1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde (1 mol) and 2-hydroxybenzohydrazide (1 mol) were added in 50 ml ethanol and add 3–4 drops of conc. H2SO4. The mixture was refluxed with stirring for 5 h at 70 °C on water bath. The reaction mixture was kept at room temperature overnight and white crystals were obtained. These were filtered, washed with cooled methanol, dried and recrystallized from methanol.

Refinement

C-bound H atoms were positioned with idealized geometry with C—H = 0.93 Å for aromatic and C—H = 0.96 Å for methyl group, and were refined using a riding model with Uiso(H) = 1.2Ueq(C) for aromatic or 1.5Ueq(C) for methyl carbon atoms. The N and O-bound H atoms were located in a difference Fourier map and the positional parameters were refined with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O); the refined distances are N—H = 0.978 (18) Å and O—H = 0.95 (2) Å

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, with 50% displacement ellipsoids. The hydrogen bonds are shown with dashed lines.

Crystal data

C19H18N4O3 F(000) = 1472
Mr = 350.37 Dx = 1.385 Mg m−3
Monoclinic, C2/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc Cell parameters from 3642 reflections
a = 25.2357 (6) Å θ = 2.5–25.1°
b = 8.5624 (2) Å µ = 0.10 mm−1
c = 16.0329 (4) Å T = 296 K
β = 104.048 (1)° Needle, colorless
V = 3360.75 (14) Å3 0.22 × 0.06 × 0.05 mm
Z = 8
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Data collection

Bruker Kappa APEXII CCD diffractometer 4174 independent reflections
Radiation source: fine-focus sealed tube 2653 reflections with I > 2σ(I)
graphite Rint = 0.029
φ and ω scans θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007) h = −33→32
Tmin = 0.980, Tmax = 0.995 k = −11→11
16063 measured reflections l = −21→21
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Refinement

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)] = 0.043 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119 H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.9211P] where P = (Fo2 + 2Fc2)/3
4174 reflections (Δ/σ)max < 0.001
243 parameters Δρmax = 0.16 e Å−3
0 restraints Δρmin = −0.19 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.46453 (5) 0.76202 (15) 0.40473 (7) 0.0576 (3)
O2 0.64520 (4) 0.88611 (14) 0.58892 (7) 0.0528 (3)
O3 0.69778 (5) 1.07722 (17) 0.52182 (8) 0.0604 (4)
N1 0.38948 (5) 0.63069 (15) 0.42694 (7) 0.0411 (3)
N2 0.37762 (5) 0.53986 (16) 0.49225 (8) 0.0418 (3)
N3 0.55797 (5) 0.72973 (16) 0.59800 (8) 0.0461 (3)
N4 0.55879 (5) 0.81534 (15) 0.52518 (8) 0.0400 (3)
C1 0.35469 (6) 0.63351 (18) 0.34260 (9) 0.0371 (3)
C2 0.32860 (6) 0.49921 (19) 0.30573 (10) 0.0431 (4)
H2 0.3357 0.4037 0.3339 0.052*
C3 0.29185 (6) 0.5090 (2) 0.22647 (11) 0.0490 (4)
H3 0.2730 0.4203 0.2022 0.059*
C4 0.28296 (6) 0.6486 (2) 0.18339 (10) 0.0504 (4)
H4 0.2579 0.6546 0.1303 0.060*
C5 0.31115 (7) 0.7800 (2) 0.21888 (11) 0.0497 (4)
H5 0.3061 0.8736 0.1886 0.060*
C6 0.34670 (6) 0.77364 (19) 0.29874 (10) 0.0440 (4)
H6 0.3652 0.8629 0.3230 0.053*
C7 0.44219 (6) 0.68619 (19) 0.45316 (9) 0.0405 (4)
C8 0.46208 (6) 0.63199 (18) 0.53974 (9) 0.0379 (3)
C9 0.42086 (6) 0.54514 (18) 0.56011 (9) 0.0391 (4)
C10 0.51460 (6) 0.6533 (2) 0.59932 (9) 0.0455 (4)
H10 0.5176 0.5990 0.6505 0.055*
C11 0.60540 (6) 0.89180 (17) 0.52552 (9) 0.0381 (3)
C12 0.60884 (6) 0.98077 (18) 0.44780 (9) 0.0384 (4)
C13 0.65628 (6) 1.06824 (19) 0.45021 (10) 0.0423 (4)
C14 0.66193 (7) 1.1489 (2) 0.37797 (11) 0.0520 (4)
H14 0.6933 1.2075 0.3802 0.062*
C15 0.62176 (8) 1.1429 (2) 0.30318 (11) 0.0545 (4)
H15 0.6261 1.1964 0.2548 0.065*
C16 0.57499 (8) 1.0581 (2) 0.29950 (11) 0.0567 (5)
H16 0.5478 1.0541 0.2487 0.068*
C17 0.56846 (7) 0.9792 (2) 0.37078 (10) 0.0495 (4)
H17 0.5364 0.9235 0.3678 0.059*
C18 0.32105 (7) 0.5084 (2) 0.49384 (11) 0.0549 (5)
H18A 0.3183 0.5003 0.5524 0.082*
H18B 0.3094 0.4122 0.4644 0.082*
H18C 0.2982 0.5921 0.4658 0.082*
C19 0.42026 (7) 0.4633 (2) 0.64200 (10) 0.0536 (4)
H19A 0.3935 0.3815 0.6307 0.080*
H19B 0.4113 0.5365 0.6818 0.080*
H19C 0.4556 0.4193 0.6662 0.080*
H4N 0.5272 (7) 0.812 (2) 0.4759 (11) 0.064*
H3O 0.6855 (9) 1.012 (2) 0.5610 (13) 0.080*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0432 (6) 0.0856 (9) 0.0391 (6) −0.0239 (6) 0.0004 (5) 0.0156 (6)
O2 0.0401 (6) 0.0670 (8) 0.0431 (6) −0.0113 (6) −0.0058 (5) 0.0095 (5)
O3 0.0418 (7) 0.0787 (9) 0.0547 (8) −0.0157 (6) 0.0001 (6) 0.0107 (6)
N1 0.0359 (7) 0.0532 (8) 0.0339 (7) −0.0077 (6) 0.0080 (5) 0.0031 (6)
N2 0.0380 (7) 0.0511 (8) 0.0388 (7) −0.0065 (6) 0.0141 (6) 0.0016 (6)
N3 0.0427 (8) 0.0572 (9) 0.0342 (7) −0.0076 (7) 0.0010 (6) 0.0060 (6)
N4 0.0358 (7) 0.0470 (8) 0.0331 (7) −0.0045 (6) 0.0001 (5) 0.0042 (6)
C1 0.0298 (7) 0.0484 (9) 0.0334 (7) −0.0019 (6) 0.0083 (6) −0.0051 (7)
C2 0.0414 (9) 0.0445 (9) 0.0440 (9) −0.0030 (7) 0.0117 (7) −0.0051 (7)
C3 0.0409 (9) 0.0573 (11) 0.0488 (10) −0.0091 (8) 0.0111 (8) −0.0149 (8)
C4 0.0360 (9) 0.0707 (13) 0.0406 (9) 0.0002 (8) 0.0021 (7) −0.0055 (8)
C5 0.0464 (10) 0.0539 (11) 0.0466 (9) 0.0041 (8) 0.0073 (8) 0.0046 (8)
C6 0.0422 (9) 0.0451 (10) 0.0439 (9) −0.0052 (7) 0.0088 (7) −0.0046 (7)
C7 0.0368 (8) 0.0485 (9) 0.0346 (8) −0.0068 (7) 0.0058 (6) −0.0012 (7)
C8 0.0376 (8) 0.0437 (9) 0.0325 (8) −0.0018 (7) 0.0084 (6) −0.0025 (6)
C9 0.0407 (8) 0.0431 (9) 0.0354 (8) −0.0003 (7) 0.0130 (7) −0.0025 (6)
C10 0.0451 (9) 0.0570 (11) 0.0322 (8) −0.0048 (8) 0.0053 (7) 0.0058 (7)
C11 0.0341 (8) 0.0388 (8) 0.0377 (8) −0.0008 (6) 0.0014 (6) −0.0019 (6)
C12 0.0361 (8) 0.0382 (9) 0.0387 (8) 0.0016 (6) 0.0046 (7) 0.0006 (6)
C13 0.0382 (8) 0.0425 (9) 0.0439 (9) −0.0007 (7) 0.0058 (7) −0.0001 (7)
C14 0.0512 (10) 0.0506 (11) 0.0555 (10) −0.0083 (8) 0.0157 (8) 0.0043 (8)
C15 0.0652 (12) 0.0527 (11) 0.0464 (10) −0.0001 (9) 0.0155 (9) 0.0086 (8)
C16 0.0574 (11) 0.0642 (12) 0.0414 (10) −0.0053 (9) −0.0017 (8) 0.0081 (8)
C17 0.0448 (9) 0.0551 (11) 0.0436 (9) −0.0078 (8) 0.0011 (7) 0.0065 (8)
C18 0.0400 (9) 0.0760 (13) 0.0515 (10) −0.0125 (9) 0.0167 (8) 0.0009 (9)
C19 0.0559 (11) 0.0632 (12) 0.0440 (9) −0.0041 (9) 0.0165 (8) 0.0081 (8)
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Geometric parameters (Å, °)

O1—C7 1.2469 (18) C6—H6 0.9300
O2—C11 1.2445 (17) C7—C8 1.434 (2)
O3—C13 1.3553 (18) C8—C9 1.381 (2)
O3—H3O 0.95 (2) C8—C10 1.445 (2)
N1—C7 1.3785 (19) C9—C19 1.492 (2)
N1—N2 1.3940 (17) C10—H10 0.9300
N1—C1 1.4225 (18) C11—C12 1.481 (2)
N2—C9 1.3417 (19) C12—C17 1.397 (2)
N2—C18 1.4588 (19) C12—C13 1.405 (2)
N3—C10 1.280 (2) C13—C14 1.385 (2)
N3—N4 1.3830 (17) C14—C15 1.370 (2)
N4—C11 1.3450 (19) C14—H14 0.9300
N4—H4N 0.978 (18) C15—C16 1.375 (2)
C1—C6 1.381 (2) C15—H15 0.9300
C1—C2 1.384 (2) C16—C17 1.371 (2)
C2—C3 1.382 (2) C16—H16 0.9300
C2—H2 0.9300 C17—H17 0.9300
C3—C4 1.372 (2) C18—H18A 0.9600
C3—H3 0.9300 C18—H18B 0.9600
C4—C5 1.378 (2) C18—H18C 0.9600
C4—H4 0.9300 C19—H19A 0.9600
C5—C6 1.375 (2) C19—H19B 0.9600
C5—H5 0.9300 C19—H19C 0.9600
C13—O3—H3O 102.6 (13) C8—C9—C19 129.08 (14)
C7—N1—N2 109.30 (12) N3—C10—C8 134.81 (14)
C7—N1—C1 127.67 (12) N3—C10—H10 112.6
N2—N1—C1 121.87 (12) C8—C10—H10 112.6
C9—N2—N1 108.03 (12) O2—C11—N4 121.06 (14)
C9—N2—C18 126.78 (13) O2—C11—C12 120.45 (13)
N1—N2—C18 120.37 (13) N4—C11—C12 118.47 (13)
C10—N3—N4 118.23 (13) C17—C12—C13 117.59 (14)
C11—N4—N3 116.54 (12) C17—C12—C11 124.04 (14)
C11—N4—H4N 124.0 (11) C13—C12—C11 118.34 (13)
N3—N4—H4N 119.4 (11) O3—C13—C14 117.70 (14)
C6—C1—C2 120.59 (14) O3—C13—C12 122.12 (14)
C6—C1—N1 118.62 (13) C14—C13—C12 120.18 (15)
C2—C1—N1 120.77 (14) C15—C14—C13 120.58 (16)
C3—C2—C1 119.07 (15) C15—C14—H14 119.7
C3—C2—H2 120.5 C13—C14—H14 119.7
C1—C2—H2 120.5 C14—C15—C16 120.14 (16)
C4—C3—C2 120.46 (15) C14—C15—H15 119.9
C4—C3—H3 119.8 C16—C15—H15 119.9
C2—C3—H3 119.8 C17—C16—C15 119.99 (16)
C3—C4—C5 119.91 (15) C17—C16—H16 120.0
C3—C4—H4 120.0 C15—C16—H16 120.0
C5—C4—H4 120.0 C16—C17—C12 121.51 (16)
C6—C5—C4 120.50 (16) C16—C17—H17 119.2
C6—C5—H5 119.8 C12—C17—H17 119.2
C4—C5—H5 119.8 N2—C18—H18A 109.5
C5—C6—C1 119.35 (15) N2—C18—H18B 109.5
C5—C6—H6 120.3 H18A—C18—H18B 109.5
C1—C6—H6 120.3 N2—C18—H18C 109.5
O1—C7—N1 122.57 (13) H18A—C18—H18C 109.5
O1—C7—C8 131.79 (14) H18B—C18—H18C 109.5
N1—C7—C8 105.59 (13) C9—C19—H19A 109.5
C9—C8—C7 107.25 (13) C9—C19—H19B 109.5
C9—C8—C10 122.31 (14) H19A—C19—H19B 109.5
C7—C8—C10 130.42 (14) C9—C19—H19C 109.5
N2—C9—C8 109.73 (13) H19A—C19—H19C 109.5
N2—C9—C19 121.19 (14) H19B—C19—H19C 109.5
C7—N1—N2—C9 3.35 (17) N1—N2—C9—C19 178.01 (14)
C1—N1—N2—C9 171.97 (13) C18—N2—C9—C19 22.9 (2)
C7—N1—N2—C18 160.36 (14) C7—C8—C9—N2 1.00 (18)
C1—N1—N2—C18 −31.0 (2) C10—C8—C9—N2 −177.66 (14)
C10—N3—N4—C11 −178.83 (15) C7—C8—C9—C19 −179.73 (16)
C7—N1—C1—C6 −52.2 (2) C10—C8—C9—C19 1.6 (3)
N2—N1—C1—C6 141.46 (14) N4—N3—C10—C8 −0.2 (3)
C7—N1—C1—C2 128.96 (17) C9—C8—C10—N3 −177.33 (18)
N2—N1—C1—C2 −37.4 (2) C7—C8—C10—N3 4.4 (3)
C6—C1—C2—C3 −3.9 (2) N3—N4—C11—O2 −0.7 (2)
N1—C1—C2—C3 175.00 (13) N3—N4—C11—C12 178.00 (13)
C1—C2—C3—C4 2.6 (2) O2—C11—C12—C17 172.71 (15)
C2—C3—C4—C5 0.5 (2) N4—C11—C12—C17 −6.0 (2)
C3—C4—C5—C6 −2.4 (2) O2—C11—C12—C13 −5.1 (2)
C4—C5—C6—C1 1.1 (2) N4—C11—C12—C13 176.17 (14)
C2—C1—C6—C5 2.0 (2) C17—C12—C13—O3 179.98 (15)
N1—C1—C6—C5 −176.85 (14) C11—C12—C13—O3 −2.1 (2)
N2—N1—C7—O1 175.00 (15) C17—C12—C13—C14 −0.1 (2)
C1—N1—C7—O1 7.2 (3) C11—C12—C13—C14 177.82 (15)
N2—N1—C7—C8 −2.66 (17) O3—C13—C14—C15 179.16 (16)
C1—N1—C7—C8 −170.43 (14) C12—C13—C14—C15 −0.8 (3)
O1—C7—C8—C9 −176.30 (18) C13—C14—C15—C16 0.8 (3)
N1—C7—C8—C9 1.05 (17) C14—C15—C16—C17 0.1 (3)
O1—C7—C8—C10 2.2 (3) C15—C16—C17—C12 −1.0 (3)
N1—C7—C8—C10 179.56 (16) C13—C12—C17—C16 1.0 (3)
N1—N2—C9—C8 −2.65 (17) C11—C12—C17—C16 −176.83 (16)
C18—N2—C9—C8 −157.76 (16)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O3—H3O···O2 0.95 (2) 1.62 (2) 2.5076 (17) 155 (2)
N4—H4N···O1 0.978 (18) 1.763 (18) 2.7140 (16) 163.3 (16)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5039).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000402/is5039sup1.cif

e-68-0o352-sup1.cif (27.2KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000402/is5039Isup2.hkl

e-68-0o352-Isup2.hkl (204.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812000402/is5039Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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