(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{(ethane-1,2-diyldiimino)­bis­[(2-fur­yl)methyl­idyne]}di-1H-pyrazol-5(4H)-one

Wang, H.-W.

doi:10.1107/S160053681001980X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1534

doi:10.1107/S160053681001980X

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(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{(ethane-1,2-diyldiimino)bis[(2-furyl)methylidyne]}di-1H-pyrazol-5(4H)-one

Hai-Wen Wang ^a ^*

^aEast China University of Science and Technology, Collage of Chemistry and Molecular Engineering, Mei Long Road 130, Shanghai 200237, People's Republic of China
^*Correspondence e-mail: wanghaiwen@ecust.edu.cn

(Received 23 May 2010; accepted 26 May 2010; online 5 June 2010)

The complete molecule of the title compound of the title compound, C₃₂H₂₈N₆O₄, is generated by crystallographic inversion symmetry. The dihedral angles between the pyrazalone ring and the pendant phenyl and furan rings are 15.65 (8) and 65.06 (8)°, respectively. In the crystal, the molecules are linked by N—H⋯O, C—H⋯O and weak C—H⋯π interactions.

Related literature

For general background to pyrazolones, see: Casas et al. (2007 ); Jensen (1959 ); Li et al. (2000 ); Zhang et al. (2007 , 2008 ).

Experimental

Crystal data

C₃₂H₂₈N₆O₄
M_r = 560.60
Monoclinic, P 2₁ /c
a = 10.7438 (6) Å
b = 7.6999 (4) Å
c = 16.8273 (9) Å
β = 93.937 (1)°
V = 1388.77 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
8081 measured reflections
3145 independent reflections
1934 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.133
S = 1.02
3145 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.92 (2)	1.91 (2)	2.693 (2)	142.0 (17)
C16—H16A⋯Cg3ⁱ	0.97	2.70	3.575 (2)	151
C3—H3⋯O1ⁱⁱ	0.93	2.54	3.389 (2)	152
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001980X/zq2042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681001980X/zq2042Isup2.hkl

checkCIF report

Comment top

Pyrazolones form a very important class of heterocycles due to their properties and applications (Casas et al., 2007). Schiffbases derived from 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (PMFP) have found extensive application in coordination chemistry and in antibacterial activation (Zhang et al., 2007, 2008; Li et al., 2000). In order to expand this field, a novel bis-schiff base has been synthesized and its crystal structure is reported herein for the first time.

The molecular structure of the title compound (I) is shown in Fig.1. The molecule adopts a staggered conformation about the C9—C9ⁱbond (symmetry code: (i) -x, y + 1/2, -z + 1/2) due to the centrosymmetry. Atoms O1, C7, C8 and C11 of the PMFP moiety and N3 of the ethylenediamine group are almost coplanar, the largest deviation being 0.063 (11) Å for atom C11. The phenyl and furan rings are slightly twisted with respect to the central pyrazolone ring making dihedral angles of 15.65 (8)° and 65.06 (8)°, respectively, indicating a high degree of conjugation and electron delocalization.

The cohesion of the crystal is assured by a strong intramolecular hydrogen bond N3—H3A···O1 (Table 1). Three weak hydrogen bonds C2—H2···O1, C3—H3···O1 and C16–16 A···Cg(3) (Cg(3) denotes the C1—C6 ring centroid) also contribute to the stabilization of the crystal structure.

Related literature top

For general background to pyrazolones, see: Casas et al. (2007); Jensen (1959); Li et al. (2000); Zhang et al. (2007, 2008).

Experimental top

All reagents were obtained from commercial sources and used without further purification. PMFP was synthesized according to the method proposed by Jensen (Jensen, 1959). Ethylenediamine1.0 mmol (0.067 ml) was added dropwise to a stirred solution of PMFP 2.0 mmol (0.5365 g) in anhydrous ethanol (25 ml) at ambient temperature.After refluxing for 6 h, the solvent was removed and a pure yellowish product was obtained upon recrystallization from EtOH/n-heptane (V/V = 1) in 78% yield. mp: 181–182°C.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) (thermal ellipsoids are shown at the 30% probability level). Symmetry code: (i) -x, y+1/2, -z+1/2.

(E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{(ethane-1,2- diyldiimino)bis[(2-furyl)methylidyne]}di-1H-pyrazol-5(4H)-one top

Crystal data top

C₃₂H₂₈N₆O₄	F(000) = 588
M_r = 560.60	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1740 reflections
a = 10.7438 (6) Å	θ = 2.4–22.9°
b = 7.6999 (4) Å	µ = 0.09 mm⁻¹
c = 16.8273 (9) Å	T = 295 K
β = 93.937 (1)°	Block, yellow
V = 1388.77 (13) Å³	0.22 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
phi and ω scans	h = −12→13
8081 measured reflections	k = −10→6
3145 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0585P)² + 0.2282P] where P = (F_o² + 2F_c²)/3
3145 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₂H₂₈N₆O₄	V = 1388.77 (13) Å³
M_r = 560.60	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7438 (6) Å	µ = 0.09 mm⁻¹
b = 7.6999 (4) Å	T = 295 K
c = 16.8273 (9) Å	0.22 × 0.20 × 0.20 mm
β = 93.937 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1934 reflections with I > 2σ(I)
8081 measured reflections	R_int = 0.026
3145 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
3145 reflections	Δρ_min = −0.21 e Å⁻³
195 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
C1	0.79340 (17)	1.2879 (2)	0.11911 (11)	0.0503 (4)
C2	0.86997 (19)	1.2531 (3)	0.18661 (11)	0.0628 (5)
H2	0.9052	1.1435	0.1942	0.075*
C3	0.8939 (2)	1.3819 (4)	0.24275 (14)	0.0784 (7)
H3	0.9448	1.3584	0.2884	0.094*
C4	0.8430 (2)	1.5442 (4)	0.23149 (16)	0.0832 (8)
H4	0.8600	1.6308	0.2692	0.100*
C5	0.7671 (2)	1.5788 (3)	0.16450 (15)	0.0755 (7)
H5	0.7329	1.6890	0.1570	0.091*
C6	0.74101 (18)	1.4516 (3)	0.10811 (13)	0.0598 (5)
H6	0.6887	1.4753	0.0631	0.072*
C7	0.83098 (17)	1.0057 (2)	0.04804 (11)	0.0494 (4)
C8	0.76317 (16)	0.9266 (2)	−0.01917 (10)	0.0477 (4)
C9	0.66731 (17)	1.0489 (3)	−0.04361 (11)	0.0529 (5)
C10	0.5737 (2)	1.0478 (3)	−0.11395 (13)	0.0757 (7)
H10A	0.5098	0.9640	−0.1054	0.114*
H10B	0.6145	1.0178	−0.1610	0.114*
H10C	0.5369	1.1610	−0.1204	0.114*
C11	0.79841 (15)	0.7652 (2)	−0.04839 (10)	0.0453 (4)
C12	0.71716 (18)	0.6668 (2)	−0.10479 (10)	0.0510 (5)
C13	0.59548 (17)	0.6410 (3)	−0.10780 (11)	0.0566 (5)
H13	0.5408	0.6837	−0.0720	0.068*
C14	0.5636 (2)	0.5375 (3)	−0.17468 (13)	0.0728 (6)
H14	0.4841	0.4988	−0.1915	0.087*
C15	0.6675 (2)	0.5054 (3)	−0.20900 (13)	0.0743 (6)
H15	0.6733	0.4402	−0.2551	0.089*
C16	0.95252 (16)	0.5224 (2)	−0.03384 (11)	0.0498 (5)
H16A	0.9908	0.5153	−0.0843	0.060*
H16B	0.8836	0.4408	−0.0350	0.060*
H3A	0.9502 (18)	0.768 (3)	0.0148 (12)	0.072 (6)*
N1	0.76746 (14)	1.1578 (2)	0.06110 (8)	0.0525 (4)
N2	0.67014 (15)	1.1852 (2)	0.00285 (9)	0.0586 (4)
N3	0.90719 (14)	0.6974 (2)	−0.02175 (10)	0.0523 (4)
O1	0.92691 (12)	0.95452 (17)	0.08686 (8)	0.0615 (4)
O2	0.76644 (13)	0.5832 (2)	−0.16638 (8)	0.0703 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0526 (10)	0.0503 (11)	0.0489 (10)	−0.0084 (9)	0.0096 (8)	−0.0029 (9)
C2	0.0687 (13)	0.0644 (13)	0.0550 (11)	−0.0098 (11)	0.0030 (10)	−0.0045 (10)
C3	0.0795 (15)	0.0934 (19)	0.0622 (14)	−0.0174 (14)	0.0041 (11)	−0.0200 (13)
C4	0.0753 (15)	0.0879 (19)	0.0887 (18)	−0.0172 (14)	0.0219 (14)	−0.0418 (15)
C5	0.0656 (13)	0.0618 (14)	0.1014 (18)	−0.0080 (11)	0.0215 (13)	−0.0244 (13)
C6	0.0572 (11)	0.0562 (12)	0.0673 (12)	−0.0035 (10)	0.0143 (10)	−0.0061 (10)
C7	0.0528 (10)	0.0465 (10)	0.0481 (10)	0.0005 (9)	−0.0017 (8)	0.0039 (8)
C8	0.0505 (10)	0.0465 (10)	0.0452 (9)	0.0000 (8)	−0.0029 (8)	0.0006 (8)
C9	0.0550 (11)	0.0534 (11)	0.0490 (10)	0.0044 (9)	−0.0051 (8)	0.0015 (9)
C10	0.0822 (15)	0.0761 (16)	0.0647 (13)	0.0176 (13)	−0.0249 (11)	−0.0040 (12)
C11	0.0472 (10)	0.0460 (10)	0.0426 (9)	−0.0017 (8)	0.0022 (8)	0.0051 (8)
C12	0.0622 (12)	0.0480 (10)	0.0425 (9)	−0.0011 (9)	0.0002 (8)	−0.0025 (8)
C13	0.0475 (10)	0.0667 (13)	0.0559 (11)	0.0026 (9)	0.0049 (8)	−0.0122 (10)
C14	0.0565 (12)	0.0862 (17)	0.0741 (14)	−0.0062 (12)	−0.0086 (11)	−0.0161 (12)
C15	0.0718 (14)	0.0852 (16)	0.0641 (13)	−0.0018 (13)	−0.0076 (11)	−0.0288 (12)
C16	0.0482 (10)	0.0454 (10)	0.0561 (11)	−0.0007 (8)	0.0052 (8)	−0.0022 (8)
N1	0.0594 (9)	0.0474 (9)	0.0494 (9)	0.0036 (8)	−0.0063 (7)	−0.0026 (7)
N2	0.0625 (10)	0.0552 (10)	0.0564 (9)	0.0090 (8)	−0.0087 (8)	−0.0015 (8)
N3	0.0497 (9)	0.0426 (9)	0.0636 (10)	−0.0014 (7)	−0.0020 (8)	−0.0042 (8)
O1	0.0619 (8)	0.0561 (8)	0.0635 (8)	0.0046 (7)	−0.0177 (7)	−0.0037 (7)
O2	0.0630 (9)	0.0847 (11)	0.0632 (9)	0.0002 (8)	0.0047 (7)	−0.0147 (8)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C10—H10A	0.9600
C1—C6	1.387 (3)	C10—H10B	0.9600
C1—N1	1.413 (2)	C10—H10C	0.9600
C2—C3	1.382 (3)	C11—N3	1.330 (2)
C2—H2	0.9300	C11—C12	1.457 (2)
C3—C4	1.372 (4)	C12—C13	1.320 (2)
C3—H3	0.9300	C12—O2	1.358 (2)
C4—C5	1.371 (4)	C13—C14	1.402 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.379 (3)	C14—C15	1.315 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—O2	1.378 (2)
C7—O1	1.246 (2)	C15—H15	0.9300
C7—N1	1.380 (2)	C16—N3	1.452 (2)
C7—C8	1.438 (2)	C16—C16ⁱ	1.516 (3)
C8—C11	1.398 (3)	C16—H16A	0.9700
C8—C9	1.435 (2)	C16—H16B	0.9700
C9—N2	1.307 (2)	N1—N2	1.399 (2)
C9—C10	1.500 (2)	N3—H3A	0.92 (2)

C2—C1—C6	119.95 (18)	H10A—C10—H10C	109.5
C2—C1—N1	120.52 (18)	H10B—C10—H10C	109.5
C6—C1—N1	119.54 (17)	N3—C11—C8	118.92 (16)
C3—C2—C1	119.7 (2)	N3—C11—C12	119.25 (17)
C3—C2—H2	120.2	C8—C11—C12	121.79 (16)
C1—C2—H2	120.2	C13—C12—O2	109.65 (16)
C4—C3—C2	120.4 (2)	C13—C12—C11	130.61 (17)
C4—C3—H3	119.8	O2—C12—C11	119.74 (16)
C2—C3—H3	119.8	C12—C13—C14	107.65 (18)
C5—C4—C3	119.9 (2)	C12—C13—H13	126.2
C5—C4—H4	120.0	C14—C13—H13	126.2
C3—C4—H4	120.0	C15—C14—C13	106.94 (18)
C4—C5—C6	120.6 (2)	C15—C14—H14	126.5
C4—C5—H5	119.7	C13—C14—H14	126.5
C6—C5—H5	119.7	C14—C15—O2	109.74 (18)
C5—C6—C1	119.5 (2)	C14—C15—H15	125.1
C5—C6—H6	120.3	O2—C15—H15	125.1
C1—C6—H6	120.3	N3—C16—C16ⁱ	108.70 (18)
O1—C7—N1	125.83 (17)	N3—C16—H16A	109.9
O1—C7—C8	129.37 (17)	C16ⁱ—C16—H16A	109.9
N1—C7—C8	104.79 (15)	N3—C16—H16B	109.9
C11—C8—C9	133.55 (16)	C16ⁱ—C16—H16B	109.9
C11—C8—C7	121.23 (16)	H16A—C16—H16B	108.3
C9—C8—C7	105.20 (16)	C7—N1—N2	111.73 (14)
N2—C9—C8	111.62 (16)	C7—N1—C1	129.44 (15)
N2—C9—C10	117.60 (17)	N2—N1—C1	118.64 (15)
C8—C9—C10	130.68 (18)	C9—N2—N1	106.47 (15)
C9—C10—H10A	109.5	C11—N3—C16	127.80 (16)
C9—C10—H10B	109.5	C11—N3—H3A	112.4 (12)
H10A—C10—H10B	109.5	C16—N3—H3A	119.0 (13)
C9—C10—H10C	109.5	C12—O2—C15	106.01 (15)

C6—C1—C2—C3	−0.1 (3)	C8—C11—C12—O2	139.07 (18)
N1—C1—C2—C3	−179.80 (18)	O2—C12—C13—C14	−0.6 (2)
C1—C2—C3—C4	−0.6 (3)	C11—C12—C13—C14	179.5 (2)
C2—C3—C4—C5	0.6 (4)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C13—C14—C15—O2	0.6 (3)
C4—C5—C6—C1	−0.7 (3)	O1—C7—N1—N2	174.61 (17)
C2—C1—C6—C5	0.7 (3)	C8—C7—N1—N2	−4.5 (2)
N1—C1—C6—C5	−179.56 (17)	O1—C7—N1—C1	−0.1 (3)
O1—C7—C8—C11	3.0 (3)	C8—C7—N1—C1	−179.26 (17)
N1—C7—C8—C11	−177.92 (16)	C2—C1—N1—C7	−19.0 (3)
O1—C7—C8—C9	−175.32 (19)	C6—C1—N1—C7	161.30 (18)
N1—C7—C8—C9	3.75 (19)	C2—C1—N1—N2	166.60 (16)
C11—C8—C9—N2	−179.9 (2)	C6—C1—N1—N2	−13.1 (2)
C7—C8—C9—N2	−1.9 (2)	C8—C9—N2—N1	−0.8 (2)
C11—C8—C9—C10	−3.7 (4)	C10—C9—N2—N1	−177.56 (17)
C7—C8—C9—C10	174.3 (2)	C7—N1—N2—C9	3.4 (2)
C9—C8—C11—N3	167.09 (19)	C1—N1—N2—C9	178.82 (16)
C7—C8—C11—N3	−10.7 (3)	C8—C11—N3—C16	169.17 (17)
C9—C8—C11—C12	−15.3 (3)	C12—C11—N3—C16	−8.5 (3)
C7—C8—C11—C12	166.92 (16)	C16ⁱ—C16—N3—C11	−154.74 (19)
N3—C11—C12—C13	136.6 (2)	C13—C12—O2—C15	0.9 (2)
C8—C11—C12—C13	−41.0 (3)	C11—C12—O2—C15	−179.14 (18)
N3—C11—C12—O2	−43.3 (2)	C14—C15—O2—C12	−0.9 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–c6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.92 (2)	1.91 (2)	2.693 (2)	142.0 (17)
C16—H16A···Cg3ⁱⁱ	0.97	2.70	3.575 (2)	151
C3—H3···O1ⁱⁱⁱ	0.93	2.54	3.389 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈N₆O₄
M_r	560.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.7438 (6), 7.6999 (4), 16.8273 (9)
β (°)	93.937 (1)
V (Å³)	1388.77 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8081, 3145, 1934
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 1.02
No. of reflections	3145
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–c6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.92 (2)	1.91 (2)	2.693 (2)	142.0 (17)
C16—H16A···Cg3ⁱ	0.97	2.70	3.575 (2)	151
C3—H3···O1ⁱⁱ	0.93	2.54	3.389 (2)	152

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

Acknowledgements

This work was supported by the College of Chemistry and Molecular Engineering, East China University of Science and Technology.

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Casas, J. S., García-Tasende, M. S., Sanchez, A., Sordo, J. & Touceda, Á. (2007). Coord. Chem. Rev. 251, 1561–1589. Web of Science CrossRef CAS Google Scholar
Jensen, B. S. (1959). Acta Chem. Scand. 13, 1668–1670. CrossRef CAS Web of Science Google Scholar
Li, J.-Z., Li, G. & Yu, W.-J. (2000). J. Rare Earth, 18, 233–236. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, H.-Q., Li, J.-Z., Zhang, Y. & Zhang, D. (2008). Chin. Inorg. Chem. 24, 990–993. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 7| July 2010| Page o1534

doi:10.1107/S160053681001980X

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

(E,E)-3,3′-Di­methyl-1,1′-di­phenyl-4,4′-{(ethane-1,2-diyldi­imino)­bis­­[(2-fur­yl)methyl­­idyne]}di-1H-pyrazol-5(4H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{(ethane-1,2-diyldiimino)bis[(2-furyl)methylidyne]}di-1H-pyrazol-5(4H)-one