Crystal structure of 4-[(E)-(4-hy­droxy­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Joel T Mague; Mehmet Akkurt; Shaaban K Mohamed; Alaa F Mohamed; Mustafa R Albayati

doi:10.1107/S2056989015021325

. 2015 Nov 14;71(Pt 12):o947–o948. doi: 10.1107/S2056989015021325

Crystal structure of 4-[(E)-(4-hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Joel T Mague ^a, Mehmet Akkurt ^b, Shaaban K Mohamed ^c,^d, Alaa F Mohamed ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4719916 PMID: 26870544

Abstract

The asymmetric unit of the title compound, C₁₈H₁₇N₃O₂, comprises three independent molecules (1, 2 and 3). In molecule 1, the dihedral angles between the pyrazolone ring and the pendant phenyl and hydroxybenzene rings are 54.43 (6) and 28.72 (6)°, respectively. The corresponding data for molecule 2 are 86.84 (6) and 25.69 (5)°, respectively, and for molecule 3 are 47.41 (7) and 17.09 (7)°, respectively. The three molecules feature an intramolecular C—H⋯O interaction, which closes an S(6) ring in each case. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, which generate [100] chains incorporating all three asymmetric molecules. Two weak C—H⋯O interactions connect three independent molecules to each other along the c-axis direction.

Keywords: crystal structure, pyrazolones, bio-active motifs, hydrogen bonding

Related literature

For the biological activities of the pyrazolone ring system, see: Nirali & Maulik (2010 ▸); Rahat et al. (2008 ▸); Thakkar & Joshi (2010 ▸); Mahmoud et al. (2011 ▸); Tripathy et al. (2007 ▸); Brune (1997 ▸); Abdel-Aziz et al. (2009 ▸). For industrial applications, see: Karci & Ertan (2002 ▸); Khalil et al. (2005 ▸); Ho (2005 ▸). graphic file with name e-71-0o947-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₇N₃O₂
M _r = 307.35
Triclinic,
a = 8.1214 (7) Å
b = 12.5405 (10) Å
c = 23.1875 (19) Å
α = 91.121 (1)°
β = 90.199 (1)°
γ = 90.748 (1)°
V = 2360.9 (3) Å³
Z = 6
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.30 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T _min = 0.86, T _max = 0.99
22491 measured reflections
11415 independent reflections
7110 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.115
S = 0.97
11415 reflections
628 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015b ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015021325/hb7540sup1.cif

e-71-0o947-sup1.cif^{(688.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021325/hb7540Isup2.hkl

e-71-0o947-Isup2.hkl^{(625KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015021325/hb7540Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015021325/hb7540fig1.tif

The asymmetric unit with labeling scheme and 50% probability ellipsoids. The O—H⋯O hydrogen bonds are shown as dotted lines.

Click here for additional data file.^{(1.4MB, tif)}

a . DOI: 10.1107/S2056989015021325/hb7540fig2.tif

The unit-cell contents viewed down the a axis. Intermolecular O—H⋯O and C—H⋯O hydrogen bonds are shown, respectively, as red and black dotted lines.

CCDC reference: 1436039

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.84	1.86	2.6947 (14)	170
O3—H3A⋯O6ⁱ	0.84	1.86	2.6993 (15)	175
O5—H5A⋯O4	0.84	1.88	2.7218 (15)	179
C7—H7⋯O2	0.95	2.30	3.009 (2)	131
C25—H25⋯O4	0.95	2.46	3.0612 (18)	121
C43—H43⋯O6	0.95	2.36	2.9989 (18)	124
C33—H33⋯O6ⁱⁱ	0.95	2.42	3.168 (2)	135
C35—H35⋯O2ⁱⁱ	0.95	2.31	3.122 (2)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

The pyrazolone ring system is an important structural moiety found in numerous pharmaceutically active compounds. This is mainly due to the ease preparation and the important versatile pharmaceutical and industrial applications. Pyrazolones are mostly useful as anti-inflammatory and analgesic activities (Nirali & Maulik, 2010), but in recent times, they are known to exhibit anti-cancer (Rahat et al., 2008), anti-bacterial (Thakkar & Joshi, 2010) and several other pharmacological actions like anti-fungal (Mahmoud et al., 2011), protein kinase inhibitor (Tripathy et al., 2007), anti-pyretic (Brune, 1997), anti-convulsant (Abdel-Aziz et al., 2009). In addition, they have been used as plant growth regulator, herbicidal and as an azo-dyes (Karci & Ertan, 2002; Khalil et al., 2005; Ho, 2005). Based on such findings and following to our on-going study, we report herein the synthesis and crystal structure of the title compound.

For the title compound there are three independent molecules in the asymmetric unit (Fig. 1) which differ in their conformations. In molecules 1 - 3, respectively, the maximum deviations from the mean planes of the pyrazolone rings are 0.0501 (8) Å (N3), 0.0305 (8) Å (N5) and -0.0367 (8) Å (N8). In molecule 1 the dihedral angles between the mean plane of the pyrazolone ring and those of the phenyl and hydroxyphenyl substituents are, respectively, 54.43 (6)° and 28.72 (6)°. In molecule 2 the corresponding angles are 86.84 (6) and 25.69 (5)° while in molecule 3 they are 47.41 (7) and 17.09 (7)°. In the asymmetric unit, molecules 1 and 3,respectively, form O1—H1···O4 and O5—H5A···O4 hydrogen bonds which tie the unit together (Fig. 1 and Table 1) while O3—H3A···O6ⁱ (i: x - 1, y, z) hydrogen bonds aid in the packing (Fig. 2 and Table 1).