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

Aslam, M.; Anis, I.; Afza, N.; Ejaz; Khan, I.U.; Arshad, M.N.

doi:10.1107/S1600536812000402

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o352

doi:10.1107/S1600536812000402

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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 and Muhammad Nadeem Arshad ^d ^*

^aPakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi 75280, Pakistan, ^bDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, ^cMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^dDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan
^*Correspondence e-mail: maslamchemist@hotmail.com, mnachemist@hotmail.com

(Received 23 December 2011; accepted 5 January 2012; online 11 January 2012)

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 ).

Experimental

Crystal data

C₁₉H₁₈N₄O₃
M_r = 350.37
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 1.02
4174 reflections
243 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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)

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000402/is5039sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812000402/is5039Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with 50% displacement ellipsoids. The hydrogen bonds are shown with dashed lines.

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

Crystal data top

C₁₉H₁₈N₄O₃	F(000) = 1472
M_r = 350.37	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	4174 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −33→32
T_min = 0.980, T_max = 0.995	k = −11→11
16063 measured reflections	l = −21→21

Refinement top

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(F_o²) + (0.0527P)² + 0.9211P] where P = (F_o² + 2F_c²)/3
4174 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₈N₄O₃	V = 3360.75 (14) Å³
M_r = 350.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.2357 (6) Å	µ = 0.10 mm⁻¹
b = 8.5624 (2) Å	T = 296 K
c = 16.0329 (4) Å	0.22 × 0.06 × 0.05 mm
β = 104.048 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4174 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2653 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.995	R_int = 0.029
16063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
4174 reflections	Δρ_min = −0.19 e Å⁻³
243 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₃
M_r	350.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	25.2357 (6), 8.5624 (2), 16.0329 (4)
β (°)	104.048 (1)
V (Å³)	3360.75 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.06 × 0.05

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.980, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	16063, 4174, 2653
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.02
No. of reflections	4174
No. of parameters	243
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

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.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lau, K. Y., Mayr, A. & Cheung, K. K. (1999). Inorg. Chim. Acta, 285, 223–332. Web of Science CSD CrossRef CAS Google Scholar
More, S. V., Dongarkhadekar, D. V., Chavan, R. N., Jadhav, W. N., Bhusare, S. R. & Pawar, R. P. (2002). J. Indian Chem. Soc. 79, 768–769. CAS Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & de Clercq, E. (1999). Pharm. Acta Helv. 74, 11–17. CrossRef PubMed CAS Google Scholar
Safwat, H. M., Ragab, F. A., Eid, N. M. & Abdel, G. M. (1988). Egypt. J. Pharm. Sci. 29, 99–110. CAS Google Scholar
Sharma, K. P., Jolly, V. S. & Phatak, P. (1998). J. Ultrascientist Phys. Sci. 10, 263–266. CAS 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

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Volume 68| Part 2| February 2012| Page o352

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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