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

In the title compound, C(24)H(26)N(4)O(2), the complete mol-ecule 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 mol-ecule about the central C-C bond [1.566 (3) Å] is also evident [C-C-C-C torsion angle = 44.30 (14)°]. Supra-molecular layers in the bc plane are formed in the crystal packing via C-H⋯O and C-H⋯π inter-actions.

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 = 402.50

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.136

S = 0.83

2384 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009208/hg5185sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812009208/hg5185Isup3.cml

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

C24H26N4O2	F(000) = 856
Mr = 402.50	Dx = 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

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

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(Fo2) + (0.104P)2 + 1.4411P] where P = (Fo2 + 2Fc2)/3
2384 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .