4-[3,4-Dimethyl-1-(4-methyl­phen­yl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-5-one

Wardell, S.M.S.V.; Howie, A.H.; Tiekink, E.R.T.; Wardell, J.L.

doi:10.1107/S1600536812009208

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o992-o993

doi:10.1107/S1600536812009208

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4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one

Solange M. S. V. Wardell,^a Alan H. Howie,^b Edward R. T. Tiekink ^c ^* and James L. Wardell ^d ‡

^aCHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 1 March 2012; accepted 1 March 2012; online 10 March 2012)

In the title compound, C₂₄H₂₆N₄O₂, the complete molecule is generated by the application of twofold symmetry. The pyrazole ring is approximately planar [r.m.s. deviation = 0.026 Å] and the benzene ring is twisted out of this plane [dihedral angle = 21.94 (7)°]. A twist in the molecule about the central C—C bond [1.566 (3) Å] is also evident [C—C—C—C torsion angle = 44.30 (14)°]. Supramolecular layers in the bc plane are formed in the crystal packing via C—H⋯O and C—H⋯π interactions.

Related literature

For the therapeutic importance of pyrazole compounds, see: Sil et al. (2005 ); Haddad et al. (2004 ). For the diverse pharmacological activities of pyrazole compounds, see: Bekhit et al. (2010 , 2012 ); Higashi et al. (2006 ). For synthetic background, see: Nef (1891 ): Veibel & Westöö (1953 ); Katritzky et al. (1997 ); Wardell et al. (2007 ); de Lima et al. (2010 ). For the synthesis of the title compound, see: Bernstein et al. (1947 ); Gryazeva & Golomolzin (2003 ).

Experimental

Crystal data

C₂₄H₂₆N₄O₂
M_r = 402.50
Monoclinic, C 2/c
a = 23.0007 (8) Å
b = 6.6712 (2) Å
c = 13.5967 (5) Å
β = 92.566 (2)°
V = 2084.22 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.48 × 0.36 × 0.18 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ) T_min = 0.668, T_max = 0.746
11383 measured reflections
2384 independent reflections
1856 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.136
S = 0.83
2384 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O1ⁱ	0.98	2.60	3.5676 (16)	169
C4—H4A⋯Cg1ⁱⁱ	0.98	2.82	3.6644 (15)	145
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009208/hg5185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009208/hg5185Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009208/hg5185Isup3.cml

checkCIF report

Comment top

Pyrazoles are key structures in numerous compounds of therapeutic importance (Sil et al., 2005, Haddad et al., 2004). Compounds containing this ring system are known to display diverse pharmacological activities, for example as anti-malarial agents (Bekhit et al., 2012), anti-inflammatory agents (Bekhit et al., 2010), and against cardiovascular disease (Higashi et al., 2006). A general route to pyrazole derivatives involves reaction of an arylhydrazine, ArNHNH₂, with a β-dicarbonyl compound, R'COCH₂COY. This reaction provides initially a hydrazone derivative, RNHN=CR'CH₂COY, which can be isolated but which readily undergoes cyclization to a pyrazone derivative (Nef, 1891; Katritzky et al., 1997; Wardell et al., 2007; de Lima et al., 2010). However, in some cases (Veibel & Westöö, 1953), a dimeric oxidation product is isolated, as found in the reaction between 4-MeC₆H₄NHNH₂ and MeCOCH₂CO₂Et. The structure of this product, 4-[3,4-dimethyl-1-(4-methylphenyl)-5-oxopyrazol-4- yl]-4,5-dimethyl-2-(4-methylphenyl)pyrazol-3-one (I), is now reported.

The molecule of (I), Fig. 1, has crystallographically imposed twofold symmetry. The pyrazole ring is planar with a r.m.s. deviation for the fitted atoms of 0.026 Å; the maximum deviations from this plane are 0.019 (1) Å (for the N1 and C2 atoms) and -0.023 (1) Å (C3). The benzene ring is inclined to this plane forming a dihedral angle of 21.94 (7)°. There is a twist in the molecule about the central C—C bond [1.566 (3) Å] with the C1—C2—C2ⁱ—C1ⁱ torsion angle being 44.30 (14)°; symmetry operation i: -x, y, 3/2 - z. The dihedral angle between the pyrazole rings is 61.78 (4)°.

In the crystal packing, supramolecular layers in the bc plane are formed by C—H···O and C—H···π interactions, Fig. 2 and Table 1. These stack along the a axis with no specific intermolecular interactions between them, Fig. 3.

Related literature top

For the therapeutic importance of pyrazole compounds, see: Sil et al. (2005); Haddad et al. (2004). For the diverse pharmacological activities of pyrazole compounds, see: Bekhit et al. (2010, 2012); Higashi et al. (2006). For synthetic background, see: Nef (1891): Veibel & Westöö (1953); Katritzky et al. (1997); Wardell et al. (2007); de Lima et al. (2010). For the synthesis of the title compound, see: Bernstein et al. (1947); Gryazeva & Golomolzin (2003).

Experimental top

A solution of 4-MeC₆H₄NHNH₂.HCl (2 mmol) and MeCOCH₂CO₂Et (2 mmol) in EtOH (2 0 ml) was refluxed for 2 h. The reaction was left to slowly evaporate in air. Crystals were collected after a week, M.pt: > 573 K; lit. M.pt: >573 K (Bernstein et al., 1947; Gryazeva & Golomolzin, 2003). IR ν: 3391, 3084, 3041, 3012, 2974, 2920, 2858, 1706, 1663, 1614, 1511, 1441, 1390, 1363, 1288, 1140, 1083, 1004, 912, 816, 776, 654, 590, 507, 485 cm^-1.

Structure description top

For the therapeutic importance of pyrazole compounds, see: Sil et al. (2005); Haddad et al. (2004). For the diverse pharmacological activities of pyrazole compounds, see: Bekhit et al. (2010, 2012); Higashi et al. (2006). For synthetic background, see: Nef (1891): Veibel & Westöö (1953); Katritzky et al. (1997); Wardell et al. (2007); de Lima et al. (2010). For the synthesis of the title compound, see: Bernstein et al. (1947); Gryazeva & Golomolzin (2003).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Unlabelled atoms are related by the symmetry operation -x, y, 3/2 - z.
	Fig. 2. A view of the supramolecular layer in the bc plane of (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively. Hydrogen atoms not involved in intermolecular interactions have been omitted for reasons of clarity.
	Fig. 3. A view in projection down the b axis of the stacking of supramolecular layers along the a direction in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.

4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]- 3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one top

Crystal data top

C₂₄H₂₆N₄O₂	F(000) = 856
M_r = 402.50	D_x = 1.283 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6506 reflections
a = 23.0007 (8) Å	θ = 2.9–27.5°
b = 6.6712 (2) Å	µ = 0.08 mm⁻¹
c = 13.5967 (5) Å	T = 120 K
β = 92.566 (2)°	Block, light-yellow
V = 2084.22 (12) Å³	0.48 × 0.36 × 0.18 mm
Z = 4

Data collection top

Rigaku Saturn724+ diffractometer	2384 independent reflections
Radiation source: Rotating Anode	1856 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.042
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
profile data from ω–scans	h = −29→29
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −8→8
T_min = 0.668, T_max = 0.746	l = −17→17
11383 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.104P)² + 1.4411P] where P = (F_o² + 2F_c²)/3
2384 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₆N₄O₂	V = 2084.22 (12) Å³
M_r = 402.50	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.0007 (8) Å	µ = 0.08 mm⁻¹
b = 6.6712 (2) Å	T = 120 K
c = 13.5967 (5) Å	0.48 × 0.36 × 0.18 mm
β = 92.566 (2)°

Data collection top

Rigaku Saturn724+ diffractometer	2384 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	1856 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.746	R_int = 0.042
11383 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.83	Δρ_max = 0.26 e Å⁻³
2384 reflections	Δρ_min = −0.18 e Å⁻³
139 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.06343 (4)	0.52970 (14)	0.91141 (7)	0.0292 (3)
N1	0.10162 (5)	0.23866 (16)	0.84739 (8)	0.0202 (3)
N2	0.09381 (5)	0.12079 (17)	0.76120 (8)	0.0217 (3)
C1	0.05610 (5)	0.2093 (2)	0.70361 (9)	0.0194 (3)
C2	0.03383 (5)	0.40353 (18)	0.74559 (9)	0.0197 (3)
C3	0.06614 (6)	0.40447 (19)	0.84662 (9)	0.0205 (3)
C4	0.03921 (6)	0.1236 (2)	0.60511 (9)	0.0253 (3)
H4A	0.0658	0.0144	0.5900	0.038*
H4B	0.0413	0.2284	0.5549	0.038*
H4C	−0.0006	0.0718	0.6057	0.038*
C5	0.05690 (7)	0.5851 (2)	0.68862 (11)	0.0310 (3)
H5A	0.0993	0.5753	0.6856	0.046*
H5B	0.0468	0.7092	0.7224	0.046*
H5C	0.0392	0.5861	0.6217	0.046*
C6	0.13732 (5)	0.1626 (2)	0.92676 (9)	0.0198 (3)
C7	0.15049 (6)	−0.0403 (2)	0.93131 (10)	0.0245 (3)
H7	0.1366	−0.1285	0.8807	0.029*
C8	0.18434 (6)	−0.1132 (2)	1.01097 (10)	0.0271 (3)
H8	0.1931	−0.2523	1.0140	0.033*
C9	0.20565 (6)	0.0114 (2)	1.08617 (9)	0.0258 (3)
C10	0.19226 (6)	0.2144 (2)	1.07910 (10)	0.0282 (3)
H10	0.2065	0.3028	1.1294	0.034*
C11	0.15862 (6)	0.2913 (2)	1.00071 (10)	0.0253 (3)
H11	0.1502	0.4306	0.9974	0.030*
C12	0.24118 (7)	−0.0698 (3)	1.17294 (10)	0.0350 (4)
H12A	0.2499	−0.2116	1.1618	0.052*
H12B	0.2191	−0.0564	1.2326	0.052*
H12C	0.2776	0.0057	1.1809	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0374 (6)	0.0238 (5)	0.0256 (5)	0.0034 (4)	−0.0081 (4)	−0.0085 (4)
N1	0.0224 (6)	0.0217 (5)	0.0161 (5)	0.0010 (4)	−0.0031 (4)	−0.0038 (4)
N2	0.0221 (6)	0.0267 (6)	0.0163 (5)	0.0006 (4)	−0.0001 (4)	−0.0047 (4)
C1	0.0198 (6)	0.0233 (6)	0.0153 (6)	−0.0011 (5)	0.0025 (5)	−0.0007 (5)
C2	0.0227 (7)	0.0197 (6)	0.0163 (6)	−0.0015 (5)	−0.0021 (5)	0.0008 (5)
C3	0.0217 (6)	0.0210 (6)	0.0184 (6)	−0.0028 (5)	−0.0010 (5)	−0.0002 (5)
C4	0.0276 (7)	0.0312 (7)	0.0170 (6)	0.0030 (6)	0.0002 (5)	−0.0037 (5)
C5	0.0361 (8)	0.0295 (8)	0.0269 (7)	−0.0107 (6)	−0.0036 (6)	0.0081 (6)
C6	0.0166 (6)	0.0260 (7)	0.0167 (6)	−0.0003 (5)	0.0004 (5)	0.0003 (5)
C7	0.0237 (7)	0.0250 (7)	0.0242 (7)	−0.0012 (5)	−0.0036 (5)	−0.0025 (5)
C8	0.0257 (7)	0.0262 (7)	0.0290 (7)	0.0027 (6)	−0.0025 (6)	0.0026 (5)
C9	0.0220 (7)	0.0363 (8)	0.0191 (6)	0.0025 (6)	0.0005 (5)	0.0023 (5)
C10	0.0266 (7)	0.0350 (8)	0.0224 (7)	0.0018 (6)	−0.0051 (6)	−0.0068 (6)
C11	0.0270 (7)	0.0254 (7)	0.0232 (7)	0.0002 (6)	−0.0037 (5)	−0.0033 (5)
C12	0.0338 (8)	0.0464 (9)	0.0242 (7)	0.0091 (7)	−0.0054 (6)	0.0028 (6)

Geometric parameters (Å, º) top

O1—C3	1.2177 (15)	C5—H5C	0.9800
N1—C3	1.3743 (17)	C6—C7	1.3882 (19)
N1—N2	1.4160 (14)	C6—C11	1.3943 (18)
N1—C6	1.4202 (16)	C7—C8	1.3928 (18)
N2—C1	1.2859 (17)	C7—H7	0.9500
C1—C4	1.4917 (17)	C8—C9	1.390 (2)
C1—C2	1.5142 (17)	C8—H8	0.9500
C2—C3	1.5323 (17)	C9—C10	1.391 (2)
C2—C5	1.5446 (18)	C9—C12	1.5057 (19)
C2—C2ⁱ	1.566 (3)	C10—C11	1.3873 (19)
C4—H4A	0.9800	C10—H10	0.9500
C4—H4B	0.9800	C11—H11	0.9500
C4—H4C	0.9800	C12—H12A	0.9800
C5—H5A	0.9800	C12—H12B	0.9800
C5—H5B	0.9800	C12—H12C	0.9800

C3—N1—N2	112.79 (10)	H5A—C5—H5C	109.5
C3—N1—C6	128.04 (11)	H5B—C5—H5C	109.5
N2—N1—C6	118.56 (10)	C7—C6—C11	119.98 (12)
C1—N2—N1	107.82 (10)	C7—C6—N1	119.99 (12)
N2—C1—C4	120.81 (12)	C11—C6—N1	120.03 (12)
N2—C1—C2	113.19 (11)	C6—C7—C8	119.23 (13)
C4—C1—C2	125.98 (11)	C6—C7—H7	120.4
C1—C2—C3	100.53 (10)	C8—C7—H7	120.4
C1—C2—C5	110.64 (10)	C9—C8—C7	121.98 (13)
C3—C2—C5	106.41 (10)	C9—C8—H8	119.0
C1—C2—C2ⁱ	112.51 (8)	C7—C8—H8	119.0
C3—C2—C2ⁱ	112.02 (12)	C8—C9—C10	117.50 (13)
C5—C2—C2ⁱ	113.78 (9)	C8—C9—C12	121.48 (14)
O1—C3—N1	126.61 (12)	C10—C9—C12	121.02 (13)
O1—C3—C2	127.80 (12)	C11—C10—C9	121.84 (13)
N1—C3—C2	105.52 (10)	C11—C10—H10	119.1
C1—C4—H4A	109.5	C9—C10—H10	119.1
C1—C4—H4B	109.5	C10—C11—C6	119.47 (13)
H4A—C4—H4B	109.5	C10—C11—H11	120.3
C1—C4—H4C	109.5	C6—C11—H11	120.3
H4A—C4—H4C	109.5	C9—C12—H12A	109.5
H4B—C4—H4C	109.5	C9—C12—H12B	109.5
C2—C5—H5A	109.5	H12A—C12—H12B	109.5
C2—C5—H5B	109.5	C9—C12—H12C	109.5
H5A—C5—H5B	109.5	H12A—C12—H12C	109.5
C2—C5—H5C	109.5	H12B—C12—H12C	109.5

C3—N1—N2—C1	2.35 (15)	C1—C2—C3—N1	3.64 (12)
C6—N1—N2—C1	174.14 (10)	C5—C2—C3—N1	−111.74 (12)
N1—N2—C1—C4	178.79 (11)	C2ⁱ—C2—C3—N1	123.33 (8)
N1—N2—C1—C2	0.36 (14)	C3—N1—C6—C7	152.61 (13)
N2—C1—C2—C3	−2.51 (13)	N2—N1—C6—C7	−17.78 (17)
C4—C1—C2—C3	179.15 (12)	C3—N1—C6—C11	−26.66 (19)
N2—C1—C2—C5	109.65 (13)	N2—N1—C6—C11	162.95 (11)
C4—C1—C2—C5	−68.69 (16)	C11—C6—C7—C8	0.90 (19)
N2—C1—C2—C2ⁱ	−121.85 (13)	N1—C6—C7—C8	−178.37 (11)
C4—C1—C2—C2ⁱ	59.82 (17)	C6—C7—C8—C9	−0.3 (2)
N2—N1—C3—O1	179.21 (12)	C7—C8—C9—C10	−0.4 (2)
C6—N1—C3—O1	8.4 (2)	C7—C8—C9—C12	178.74 (12)
N2—N1—C3—C2	−3.87 (13)	C8—C9—C10—C11	0.4 (2)
C6—N1—C3—C2	−174.71 (11)	C12—C9—C10—C11	−178.70 (13)
C1—C2—C3—O1	−179.48 (13)	C9—C10—C11—C6	0.2 (2)
C5—C2—C3—O1	65.14 (17)	C7—C6—C11—C10	−0.9 (2)
C2ⁱ—C2—C3—O1	−59.80 (14)	N1—C6—C11—C10	178.41 (11)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1ⁱⁱ	0.98	2.60	3.5676 (16)	169
C4—H4A···Cg1ⁱⁱⁱ	0.98	2.82	3.6644 (15)	145

Symmetry codes: (ii) x, −y+1, z−1/2; (iii) −x+1/2, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₄O₂
M_r	402.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	23.0007 (8), 6.6712 (2), 13.5967 (5)
β (°)	92.566 (2)
V (Å³)	2084.22 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.36 × 0.18

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2011)
T_min, T_max	0.668, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11383, 2384, 1856
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 0.83
No. of reflections	2384
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.18

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1ⁱ	0.98	2.60	3.5676 (16)	169
C4—H4A···Cg1ⁱⁱ	0.98	2.82	3.6644 (15)	145

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1/2, y+1/2, −z−1/2.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

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Volume 68| Part 4| April 2012| Pages o992-o993

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

4-[3,4-Di­methyl-1-(4-methyl­phen­yl)-5-oxo-4,5-di­hydro-1H-pyrazol-4-yl]-3,4-di­methyl-1-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-5-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one