(Z)-4-[(Ethyl­amino)(furan-2-yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Li, L.-N.; Zhang, W.-G.; Huang, S.-S.; Li, C.-X.; Wang, S.-Y.

doi:10.1107/S1600536812013712

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1277

doi:10.1107/S1600536812013712

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(Z)-4-[(Ethylamino)(furan-2-yl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Li-Nan Li,^a Wei-Guo Zhang,^a Shan-Shan Huang,^b Chuan-Xun Li ^b and Shou-Yu Wang ^a ^*

^aDepartment of Orthopaedics, The First Affiliated Hospital of Dalian Medical University, Dalian 116011, People's Republic of China, and ^bCollege of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
^*Correspondence e-mail: wangshouyu88@126.com

(Received 26 March 2012; accepted 29 March 2012; online 4 April 2012)

In the crystal of the title compound, C₁₇H₁₇N₃O₂, the molecules exist in the keto–enamine form. The pyrazole ring is oriented at 10.59 (4) and 57.98 (5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30 (11)°. An intramolecular N—H⋯O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into supramolecular chains along the b axis.

Related literature

For general background to acylpyrazolones, see: Dong et al. (1983 ); Casas et al. (2007 ). For related structures, see: Zhang et al. (2007 ); Li et al. (2009 ); Wang (2010 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₂
M_r = 295.34
Orthorhombic, P b c a
a = 8.5729 (13) Å
b = 17.555 (3) Å
c = 20.427 (3) Å
V = 3074.2 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer
14892 measured reflections
3552 independent reflections
2271 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.153
S = 1.02
3552 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.98	1.87	2.702 (2)	140
C15—H15⋯O1ⁱ	0.93	2.39	3.279 (3)	161
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013712/xu5499sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013712/xu5499Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013712/xu5499Isup3.cml

checkCIF report

Comment top

1-Phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (PMFP), is a member of a family of acylpyrazolones, first synthesized in 1983 (Dong et al., 1983). Such acylpyrazolones derivatives form a very important class of heterocycles due to their properties and applications (Casas et al., 2007). We now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecular structure of (I) is shown in Fig.1. Atoms O1, C7, C8 and C11 of the PMFP moiety and atom N3 of ethylamine group are coplanar, the largest deviation being 0.0517 (11) Å for atom C8. The dihedral angle between this mean plane and pyrazole ring of PMFP is 2.73 (3)°. The bond length of C8—C11 (1.400 (2) Å) between the usual C—C and C=C bonds indicates the delocalization of the electrons because of the addition of a proton to N3 is more favorable than to O2. The atom O2 of PMFP moiety and the N3 atom of ethylamine group are on the same side of C8—C11 bond, which are available for coordination with metal cations. A strong intramolecular hydrogen bond N3—H3A···O1 (Table 1) is also indicative of the enamine-keto form. All bond lengths and angles are normal and comparable with those found in the related compounds (Zhang et al., 2007; Li et al., 2009; Wang, 2010).

Related literature top

For general background to acylpyrazolones, see: Dong et al. (1983); Casas et al. (2007). For related structures, see: Zhang et al. (2007); Li et al. (2009); Wang (2010).

Experimental top

A mixture of a 10 ml 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (2 mmol, 0.5366 g) anhydrous ethanol solution, and a 0.25 ml ethylamine (2 mmol, 0.1306 g) solution was refluxed for ca 7 h, with addition of a few drops of glacial acetic acid as a catalyst. The ethanol was removed by evaporation and the resulting green precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Yellow block single crystals suitable for analysis were obtained by slow evaporation of a solution in anhydrous ethanol at room temperature for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) (thermal ellipsoids are shown at 30% probability levels).

(Z)-4-[(Ethylamino)(furan-2-yl)methylidene]-3-methyl-1-phenyl- 1H-pyrazol-5(4H)-one top

Crystal data top

C₁₇H₁₇N₃O₂	F(000) = 1248
M_r = 295.34	D_x = 1.276 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3420 reflections
a = 8.5729 (13) Å	θ = 2.5–24.5°
b = 17.555 (3) Å	µ = 0.09 mm⁻¹
c = 20.427 (3) Å	T = 296 K
V = 3074.2 (8) Å³	Block, yellow
Z = 8	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.6°, θ_min = 2.5°
ω scans	h = −11→11
14892 measured reflections	k = −22→14
3552 independent reflections	l = −26→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.073P)² + 0.6048P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3552 reflections	Δρ_max = 0.29 e Å⁻³
202 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (11)

Crystal data top

C₁₇H₁₇N₃O₂	V = 3074.2 (8) Å³
M_r = 295.34	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.5729 (13) Å	µ = 0.09 mm⁻¹
b = 17.555 (3) Å	T = 296 K
c = 20.427 (3) Å	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2271 reflections with I > 2σ(I)
14892 measured reflections	R_int = 0.034
3552 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
3552 reflections	Δρ_min = −0.24 e Å⁻³
202 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	0.3274 (2)	0.36448 (10)	0.37402 (8)	0.0470 (4)
C2	0.4490 (2)	0.31933 (11)	0.35231 (9)	0.0568 (5)
H2	0.4819	0.3221	0.3090	0.068*
C3	0.5211 (2)	0.27020 (12)	0.39536 (10)	0.0673 (6)
H3	0.6030	0.2399	0.3807	0.081*
C4	0.4740 (3)	0.26520 (13)	0.45952 (11)	0.0719 (6)
H4	0.5234	0.2317	0.4881	0.086*
C5	0.3540 (2)	0.30984 (13)	0.48091 (10)	0.0676 (6)
H5	0.3219	0.3067	0.5243	0.081*
C6	0.2797 (2)	0.35970 (12)	0.43881 (9)	0.0561 (5)
H6	0.1981	0.3899	0.4538	0.067*
C7	0.2554 (2)	0.42127 (10)	0.26479 (8)	0.0500 (4)
C8	0.1713 (2)	0.48955 (10)	0.24974 (8)	0.0479 (4)
C9	0.1213 (2)	0.51919 (11)	0.31153 (9)	0.0502 (4)
C10	0.0283 (3)	0.58819 (12)	0.32686 (10)	0.0672 (6)
H10A	−0.0075	0.5856	0.3713	0.101*
H10B	−0.0597	0.5909	0.2979	0.101*
H10C	0.0921	0.6327	0.3213	0.101*
C11	0.1465 (2)	0.51345 (10)	0.18519 (9)	0.0506 (4)
C12	0.0770 (2)	0.58668 (10)	0.16927 (9)	0.0526 (5)
C13	−0.0461 (2)	0.60530 (12)	0.13197 (9)	0.0561 (5)
H13	−0.1068	0.5722	0.1072	0.067*
C14	−0.0655 (3)	0.68398 (15)	0.13746 (12)	0.0791 (7)
H14	−0.1426	0.7132	0.1175	0.095*
C15	0.0474 (3)	0.70936 (13)	0.17668 (12)	0.0834 (7)
H15	0.0622	0.7600	0.1884	0.100*
C16	0.1841 (3)	0.48181 (15)	0.06678 (10)	0.0774 (7)
H16A	0.2017	0.5355	0.0585	0.093*
H16B	0.0818	0.4686	0.0500	0.093*
C17	0.3046 (3)	0.43617 (17)	0.03265 (11)	0.0931 (8)
H17A	0.4054	0.4478	0.0506	0.140*
H17B	0.3036	0.4482	−0.0132	0.140*
H17C	0.2829	0.3829	0.0385	0.140*
N1	0.25453 (19)	0.41740 (8)	0.33228 (6)	0.0506 (4)
N2	0.16849 (17)	0.47679 (9)	0.36000 (7)	0.0530 (4)
N3	0.1892 (2)	0.46750 (9)	0.13692 (7)	0.0637 (5)
H3A	0.2364	0.4192	0.1514	0.076*
O1	0.31504 (18)	0.37337 (8)	0.22731 (6)	0.0658 (4)
O2	0.13911 (19)	0.64946 (9)	0.19731 (8)	0.0768 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0528 (9)	0.0412 (9)	0.0472 (9)	−0.0088 (8)	−0.0069 (7)	0.0016 (7)
C2	0.0628 (11)	0.0525 (11)	0.0552 (10)	−0.0007 (9)	−0.0040 (9)	−0.0025 (8)
C3	0.0633 (12)	0.0594 (13)	0.0793 (14)	0.0061 (10)	−0.0146 (11)	−0.0005 (11)
C4	0.0719 (13)	0.0688 (14)	0.0752 (14)	−0.0025 (12)	−0.0224 (11)	0.0189 (11)
C5	0.0685 (13)	0.0798 (15)	0.0546 (11)	−0.0114 (12)	−0.0103 (9)	0.0163 (11)
C6	0.0566 (10)	0.0607 (12)	0.0511 (10)	−0.0051 (9)	−0.0034 (8)	0.0052 (9)
C7	0.0609 (10)	0.0444 (10)	0.0446 (9)	−0.0025 (9)	−0.0018 (8)	−0.0005 (7)
C8	0.0544 (10)	0.0414 (9)	0.0477 (9)	−0.0033 (8)	−0.0040 (7)	0.0015 (8)
C9	0.0505 (9)	0.0460 (10)	0.0543 (10)	−0.0028 (8)	−0.0012 (8)	0.0005 (8)
C10	0.0674 (12)	0.0613 (13)	0.0728 (13)	0.0131 (11)	0.0052 (10)	−0.0014 (10)
C11	0.0555 (10)	0.0440 (10)	0.0523 (10)	−0.0102 (8)	−0.0052 (8)	0.0043 (8)
C12	0.0509 (10)	0.0480 (11)	0.0589 (11)	−0.0072 (8)	−0.0006 (8)	0.0074 (8)
C13	0.0508 (10)	0.0590 (12)	0.0583 (10)	−0.0014 (9)	−0.0078 (8)	0.0080 (9)
C14	0.0757 (14)	0.0754 (16)	0.0862 (16)	0.0254 (13)	0.0148 (13)	0.0283 (13)
C15	0.108 (2)	0.0462 (13)	0.0959 (17)	−0.0016 (13)	0.0296 (16)	0.0002 (12)
C16	0.1008 (17)	0.0840 (17)	0.0474 (11)	0.0017 (14)	−0.0064 (11)	0.0079 (11)
C17	0.119 (2)	0.101 (2)	0.0587 (13)	0.0073 (17)	0.0081 (13)	−0.0057 (13)
N1	0.0654 (9)	0.0447 (9)	0.0416 (7)	0.0042 (7)	−0.0013 (7)	0.0002 (6)
N2	0.0606 (9)	0.0494 (9)	0.0490 (8)	0.0035 (7)	0.0022 (7)	−0.0035 (7)
N3	0.0953 (13)	0.0510 (10)	0.0447 (8)	0.0010 (9)	−0.0074 (8)	0.0033 (7)
O1	0.0989 (11)	0.0512 (8)	0.0471 (7)	0.0146 (7)	−0.0001 (7)	−0.0042 (6)
O2	0.0834 (10)	0.0573 (9)	0.0896 (11)	−0.0112 (8)	−0.0091 (8)	0.0004 (8)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C10—H10C	0.9600
C1—C6	1.388 (3)	C11—N3	1.325 (2)
C1—N1	1.407 (2)	C11—C12	1.454 (3)
C2—C3	1.378 (3)	C12—C13	1.342 (2)
C2—H2	0.9300	C12—O2	1.352 (2)
C3—C4	1.374 (3)	C13—C14	1.396 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.365 (3)	C14—C15	1.333 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.382 (3)	C15—O2	1.379 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—N3	1.455 (2)
C7—O1	1.247 (2)	C16—C17	1.482 (3)
C7—N1	1.380 (2)	C16—H16A	0.9700
C7—C8	1.432 (3)	C16—H16B	0.9700
C8—C11	1.400 (2)	C17—H17A	0.9600
C8—C9	1.431 (2)	C17—H17B	0.9600
C9—N2	1.303 (2)	C17—H17C	0.9600
C9—C10	1.483 (3)	N1—N2	1.397 (2)
C10—H10A	0.9600	N3—H3A	0.9845
C10—H10B	0.9600

C2—C1—C6	119.58 (17)	N3—C11—C12	119.01 (16)
C2—C1—N1	121.26 (16)	C8—C11—C12	122.55 (17)
C6—C1—N1	119.12 (16)	C13—C12—O2	110.60 (17)
C3—C2—C1	119.48 (18)	C13—C12—C11	131.66 (18)
C3—C2—H2	120.3	O2—C12—C11	117.69 (16)
C1—C2—H2	120.3	C12—C13—C14	106.80 (19)
C4—C3—C2	121.1 (2)	C12—C13—H13	126.6
C4—C3—H3	119.4	C14—C13—H13	126.6
C2—C3—H3	119.4	C15—C14—C13	107.0 (2)
C5—C4—C3	119.3 (2)	C15—C14—H14	126.5
C5—C4—H4	120.3	C13—C14—H14	126.5
C3—C4—H4	120.3	C14—C15—O2	110.0 (2)
C4—C5—C6	120.8 (2)	C14—C15—H15	125.0
C4—C5—H5	119.6	O2—C15—H15	125.0
C6—C5—H5	119.6	N3—C16—C17	110.42 (19)
C5—C6—C1	119.7 (2)	N3—C16—H16A	109.6
C5—C6—H6	120.2	C17—C16—H16A	109.6
C1—C6—H6	120.2	N3—C16—H16B	109.6
O1—C7—N1	125.63 (17)	C17—C16—H16B	109.6
O1—C7—C8	129.72 (16)	H16A—C16—H16B	108.1
N1—C7—C8	104.63 (15)	C16—C17—H17A	109.5
C11—C8—C9	132.56 (17)	C16—C17—H17B	109.5
C11—C8—C7	121.97 (16)	H17A—C17—H17B	109.5
C9—C8—C7	105.42 (15)	C16—C17—H17C	109.5
N2—C9—C8	111.69 (16)	H17A—C17—H17C	109.5
N2—C9—C10	118.21 (16)	H17B—C17—H17C	109.5
C8—C9—C10	130.09 (17)	C7—N1—N2	111.78 (14)
C9—C10—H10A	109.5	C7—N1—C1	129.42 (15)
C9—C10—H10B	109.5	N2—N1—C1	118.80 (13)
H10A—C10—H10B	109.5	C9—N2—N1	106.40 (14)
C9—C10—H10C	109.5	C11—N3—C16	128.24 (18)
H10A—C10—H10C	109.5	C11—N3—H3A	114.4
H10B—C10—H10C	109.5	C16—N3—H3A	117.2
N3—C11—C8	118.44 (17)	C12—O2—C15	105.52 (17)

C6—C1—C2—C3	0.0 (3)	C8—C11—C12—O2	51.5 (2)
N1—C1—C2—C3	177.63 (17)	O2—C12—C13—C14	−1.2 (2)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C14	176.4 (2)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—C15	1.0 (2)
C3—C4—C5—C6	0.1 (3)	C13—C14—C15—O2	−0.5 (3)
C4—C5—C6—C1	0.0 (3)	O1—C7—N1—N2	−175.51 (18)
C2—C1—C6—C5	−0.1 (3)	C8—C7—N1—N2	3.0 (2)
N1—C1—C6—C5	−177.75 (17)	O1—C7—N1—C1	5.4 (3)
O1—C7—C8—C11	−1.4 (3)	C8—C7—N1—C1	−176.05 (17)
N1—C7—C8—C11	−179.86 (16)	C2—C1—N1—C7	18.6 (3)
O1—C7—C8—C9	176.14 (19)	C6—C1—N1—C7	−163.80 (18)
N1—C7—C8—C9	−2.32 (19)	C2—C1—N1—N2	−160.46 (16)
C11—C8—C9—N2	178.07 (19)	C6—C1—N1—N2	17.2 (2)
C7—C8—C9—N2	0.9 (2)	C8—C9—N2—N1	0.9 (2)
C11—C8—C9—C10	−2.1 (3)	C10—C9—N2—N1	−178.91 (15)
C7—C8—C9—C10	−179.30 (19)	C7—N1—N2—C9	−2.5 (2)
C9—C8—C11—N3	−170.12 (19)	C1—N1—N2—C9	176.65 (15)
C7—C8—C11—N3	6.7 (3)	C8—C11—N3—C16	−175.9 (2)
C9—C8—C11—C12	10.3 (3)	C12—C11—N3—C16	3.7 (3)
C7—C8—C11—C12	−172.87 (17)	C17—C16—N3—C11	153.0 (2)
N3—C11—C12—C13	54.5 (3)	C13—C12—O2—C15	0.9 (2)
C8—C11—C12—C13	−125.9 (2)	C11—C12—O2—C15	−177.06 (17)
N3—C11—C12—O2	−128.04 (19)	C14—C15—O2—C12	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.98	1.87	2.702 (2)	140
C15—H15···O1ⁱ	0.93	2.39	3.279 (3)	161

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂
M_r	295.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	8.5729 (13), 17.555 (3), 20.427 (3)
V (Å³)	3074.2 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14892, 3552, 2271
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.02
No. of reflections	3552
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.98	1.87	2.702 (2)	140
C15—H15···O1ⁱ	0.93	2.39	3.279 (3)	161

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

This work was supported by a project of the Dalian Science and Technology Bureau (No. 2009E12SF152) and the National Natural Science Foundation of China (No. 30901950).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., García-Tasende, M. S., Sánchez, A., Sordo, J. & Touceda, Á. (2007). Coord. Chem. Rev. 251, 1561–1589. CrossRef CAS Google Scholar
Dong, X.-C., Liu, F.-C. & Zhao, Y.-L. (1983). Acta Chim. Sin. 41, 848–852. CAS Google Scholar
Li, J., Li, J.-Z., Li, J.-Q., Zhang, H.-Q. & Li, J.-M. (2009). Acta Cryst. E65, o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-W. (2010). Acta Cryst. E66, o1534. Web of Science CSD CrossRef 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

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Volume 68| Part 5| May 2012| Page o1277

doi:10.1107/S1600536812013712

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

(Z)-4-[(Ethyl­amino)(furan-2-yl)methyl­­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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Experimental

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organic compounds

(Z)-4-[(Ethylamino)(furan-2-yl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one