(E)-4-(4-Hydr­oxy-3-nitro­benzyl­idene­amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Zhang, C.-N.; Yang

doi:10.1107/S1600536808030031

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1988

doi:10.1107/S1600536808030031

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(E)-4-(4-Hydroxy-3-nitrobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Chun-Niu Zhang ^a and Ming-Hua Yang ^a ^*

^aDepartment of Chemistry, Lishui University, Lishui 323000, ZheJiang, People's Republic of China
^*Correspondence e-mail: zjlsxyhx@126.com

(Received 15 September 2008; accepted 18 September 2008; online 24 September 2008)

In the title compound, C₁₈H₁₆N₄O₄, the dihedral angles between the central pyrazole ring and the pendant substituted and unsubstituted aromatic rings are 4.73 (12) and 44.24 (14)°, respectively. An intramolecular O—H⋯O hydrogen bond occurs. In the crystal structure, an intermolecular C—H⋯O interaction may help to consolidate the packing and a short intramolecular C—H⋯O contact also occurs.

Related literature

For selected background literature on Schiff bases, see: Alemi & Shaabani (2000 ); Kim & Shin (1999 ); Yan et al. (2006 ); Zheng et al. (2006 ).

Experimental

Crystal data

C₁₈H₁₆N₄O₄
M_r = 352.35
Monoclinic, P 2₁ /c
a = 7.5000 (15) Å
b = 7.8000 (16) Å
c = 28.900 (6) Å
β = 95.00 (3)°
V = 1684.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.29 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.971, T_max = 0.982
12221 measured reflections
3012 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.160
S = 0.83
3012 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.88	2.583 (3)	143
C12—H12⋯O1	0.93	2.45	3.096 (3)	127
C18—H18⋯O4ⁱ	0.93	2.38	3.079 (4)	132
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030031/hb2795sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030031/hb2795Isup2.hkl

checkCIF report

Comment top

There have been of great interest in the synthesis, characterization, and properties of Schiff bases and Schiff base complexes. (Yan et al., 2006; Zheng et al., 2006) Schiff bases that have solvent dependent UV/vis spectra (solvatochromicity) can be suitable NLO (nonlinear optical active) materials (Alemi et al., 2000). They are also useful in asymmetric oxidation of methyl phenyl sulfide and enantioselective reactions (Kim et al., 1999).

In this paper, we report here the synthesis and crystal structure of the title compound (I), (Fig. 1). The dihedral angles betweem the pyrazole ring and the pendant C13 and C1 aromatic rings are 4.73 (12)° and 44.24 (14)°, respectively. The C12—N3 bond length of 1.281 (3) Å in (I) is indicative of a normal C=N double bond.

The intra- and intermolecular hydrogen bonds in (I) are listed in Table 1.

Related literature top

For selected background literature on Schiff bases, see: Alemi & Shaabani (2000); Kim & Shin (1999); Yan et al. (2006); Zheng et al. (2006).

Experimental top

Under nitrogen, a mixture of 4-hydroxy-3-nitrobenzaldehyde (1.67 g, 10 mmol) and 4-amino-1,2-dihydro-1,5-dimethyl-1-phenylpyrazol-3-one (2.03 g, 10 mmol) in absolute ethanol (80 ml) was refluxed for about 20 h to yield a yellow precipitate. The product was collected by vacuum filtration and washed with ethanol. The crude solid was redissolved in CH₂Cl₂ (70 ml) and washed with water (2 × 8 ml) and brine (10 ml). After being dried over Na₂SO₄, the solvent was removed under vacuum, and yellow solid was isolated in a yield of 89% (2.8 g). Colourless blocks of (I) were grown from CH₂Cl₂ and absolute ethanol (4:1 v/v) by slow evaporation of the solvent at room temperature over a period of about two weeks.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I): non-H atoms are shown as 50% probability displacement ellipsoids.
	Fig. 2. The packing of (I), with C—H···O hydrogen bonds indicated by dotted lines.

(E)-4-(4-Hydroxy-3-nitrobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₁₈H₁₆N₄O₄	F(000) = 736
M_r = 352.35	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3012 reflections
a = 7.5000 (15) Å	θ = 3.2–25.2°
b = 7.8000 (16) Å	µ = 0.10 mm⁻¹
c = 28.900 (6) Å	T = 298 K
β = 95.00 (3)°	Block, colourless
V = 1684.2 (6) Å³	0.29 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3012 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ϕ and ω scans	θ_max = 25.2°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.971, T_max = 0.982	k = −9→9
12221 measured reflections	l = −34→34

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.1P)² + 0.3P] where P = (F_o² + 2F_c²)/3
3012 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₁₆N₄O₄	V = 1684.2 (6) Å³
M_r = 352.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5000 (15) Å	µ = 0.10 mm⁻¹
b = 7.8000 (16) Å	T = 298 K
c = 28.900 (6) Å	0.29 × 0.22 × 0.18 mm
β = 95.00 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3012 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1762 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.982	R_int = 0.063
12221 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 0.83	Δρ_max = 0.22 e Å⁻³
3012 reflections	Δρ_min = −0.18 e Å⁻³
238 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
N3	0.1353 (3)	0.2354 (3)	0.45196 (7)	0.0455 (5)
N1	−0.0863 (3)	0.4373 (3)	0.35252 (7)	0.0467 (5)
N2	−0.1349 (3)	0.2664 (3)	0.34216 (7)	0.0476 (5)
O1	−0.0566 (2)	−0.0019 (2)	0.37369 (6)	0.0537 (5)
O2	0.6074 (3)	−0.0082 (3)	0.63167 (6)	0.0704 (6)
H2	0.6225	−0.1096	0.6384	0.106*
O3	0.5569 (3)	−0.3329 (3)	0.61887 (8)	0.0807 (7)
O4	0.3986 (4)	−0.4244 (3)	0.55889 (10)	0.1126 (10)
N4	0.4606 (3)	−0.3063 (3)	0.58221 (9)	0.0648 (7)
C13	0.2714 (3)	0.0531 (3)	0.51068 (8)	0.0399 (6)
C12	0.1594 (3)	0.0821 (3)	0.46713 (8)	0.0429 (6)
H12	0.1064	−0.0099	0.4507	0.052*
C8	0.0330 (3)	0.2717 (3)	0.41051 (8)	0.0416 (6)
C9	0.0055 (3)	0.4366 (3)	0.39532 (8)	0.0459 (6)
C15	0.4212 (3)	−0.1337 (3)	0.56753 (8)	0.0438 (6)
C14	0.3086 (3)	−0.1094 (3)	0.52690 (8)	0.0441 (6)
H14	0.2588	−0.2037	0.5108	0.053*
C16	0.4969 (3)	0.0046 (4)	0.59269 (8)	0.0475 (6)
C1	−0.1830 (3)	0.2178 (3)	0.29503 (8)	0.0452 (6)
C18	0.3488 (3)	0.1923 (3)	0.53588 (8)	0.0469 (6)
H18	0.3255	0.3032	0.5252	0.056*
C17	0.4577 (3)	0.1682 (4)	0.57589 (9)	0.0532 (7)
H17	0.5060	0.2629	0.5920	0.064*
C5	−0.3461 (4)	0.0338 (4)	0.24047 (11)	0.0689 (9)
H5	−0.4215	−0.0597	0.2344	0.083*
C11	−0.2133 (4)	0.5723 (4)	0.33705 (10)	0.0596 (7)
H11A	−0.3240	0.5546	0.3507	0.089*
H11B	−0.2346	0.5690	0.3038	0.089*
H11C	−0.1646	0.6820	0.3465	0.089*
C6	−0.2976 (3)	0.0829 (4)	0.28630 (9)	0.0567 (7)
H6	−0.3430	0.0243	0.3107	0.068*
C7	−0.0519 (3)	0.1560 (3)	0.37629 (8)	0.0426 (6)
C2	−0.1161 (3)	0.3056 (4)	0.25858 (9)	0.0541 (7)
H2A	−0.0362	0.3958	0.2644	0.065*
C10	0.0618 (4)	0.5984 (4)	0.41979 (10)	0.0609 (8)
H10A	0.1012	0.6792	0.3978	0.091*
H10B	0.1580	0.5747	0.4430	0.091*
H10C	−0.0376	0.6456	0.4343	0.091*
C4	−0.2831 (4)	0.1223 (5)	0.20437 (10)	0.0719 (9)
H4A	−0.3176	0.0907	0.1739	0.086*
C3	−0.1694 (4)	0.2575 (4)	0.21333 (10)	0.0647 (8)
H3A	−0.1273	0.3179	0.1888	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0446 (11)	0.0477 (13)	0.0434 (11)	0.0035 (10)	−0.0014 (9)	0.0012 (10)
N1	0.0526 (12)	0.0365 (12)	0.0494 (12)	0.0018 (9)	−0.0047 (10)	0.0019 (10)
N2	0.0552 (12)	0.0400 (12)	0.0460 (12)	0.0004 (10)	−0.0053 (10)	−0.0005 (10)
O1	0.0650 (11)	0.0391 (12)	0.0553 (11)	0.0023 (9)	−0.0039 (9)	−0.0010 (8)
O2	0.0653 (12)	0.0933 (17)	0.0495 (11)	0.0028 (12)	−0.0130 (9)	−0.0004 (11)
O3	0.0720 (13)	0.0872 (17)	0.0802 (15)	0.0107 (12)	−0.0085 (12)	0.0363 (13)
O4	0.156 (3)	0.0433 (14)	0.128 (2)	0.0001 (15)	−0.046 (2)	0.0050 (15)
N4	0.0638 (15)	0.0563 (17)	0.0732 (17)	0.0019 (13)	−0.0001 (13)	0.0142 (14)
C13	0.0383 (12)	0.0411 (15)	0.0407 (13)	−0.0002 (11)	0.0055 (10)	−0.0025 (11)
C12	0.0407 (13)	0.0445 (15)	0.0432 (13)	−0.0011 (11)	0.0014 (11)	−0.0032 (12)
C8	0.0411 (13)	0.0407 (15)	0.0425 (13)	0.0012 (11)	0.0003 (11)	−0.0008 (11)
C9	0.0463 (13)	0.0438 (15)	0.0470 (14)	0.0001 (12)	0.0008 (12)	−0.0019 (12)
C15	0.0439 (13)	0.0415 (15)	0.0462 (14)	0.0022 (11)	0.0057 (11)	0.0083 (11)
C14	0.0429 (13)	0.0420 (15)	0.0474 (14)	−0.0048 (11)	0.0038 (11)	−0.0009 (11)
C16	0.0443 (13)	0.0605 (17)	0.0374 (12)	0.0003 (13)	0.0020 (11)	0.0000 (12)
C1	0.0433 (13)	0.0477 (15)	0.0429 (14)	0.0014 (12)	−0.0057 (11)	−0.0020 (12)
C18	0.0521 (14)	0.0410 (15)	0.0471 (14)	0.0015 (12)	0.0019 (12)	−0.0029 (12)
C17	0.0552 (15)	0.0544 (17)	0.0495 (15)	−0.0047 (13)	0.0017 (12)	−0.0136 (13)
C5	0.0616 (18)	0.072 (2)	0.0689 (19)	−0.0080 (16)	−0.0160 (16)	−0.0100 (17)
C11	0.0629 (17)	0.0473 (17)	0.0666 (18)	0.0118 (14)	−0.0056 (14)	0.0077 (14)
C6	0.0508 (15)	0.0625 (18)	0.0556 (16)	−0.0043 (14)	−0.0018 (13)	0.0015 (14)
C7	0.0412 (13)	0.0418 (16)	0.0446 (14)	0.0027 (11)	0.0031 (11)	0.0029 (11)
C2	0.0522 (15)	0.0580 (18)	0.0510 (15)	−0.0007 (13)	−0.0020 (12)	0.0010 (13)
C10	0.0699 (18)	0.0448 (17)	0.0655 (18)	0.0009 (14)	−0.0083 (15)	−0.0039 (14)
C4	0.078 (2)	0.084 (2)	0.0497 (17)	0.0033 (19)	−0.0156 (16)	−0.0075 (16)
C3	0.0688 (18)	0.078 (2)	0.0468 (16)	0.0034 (17)	−0.0002 (14)	0.0073 (15)

Geometric parameters (Å, º) top

N3—C12	1.281 (3)	C14—H14	0.9300
N3—C8	1.394 (3)	C16—C17	1.388 (4)
N1—C9	1.362 (3)	C1—C6	1.368 (4)
N1—N2	1.407 (3)	C1—C2	1.387 (4)
N1—C11	1.464 (3)	C18—C17	1.369 (3)
N2—C7	1.412 (3)	C18—H18	0.9300
N2—C1	1.429 (3)	C17—H17	0.9300
O1—C7	1.235 (3)	C5—C4	1.369 (4)
O2—C16	1.343 (3)	C5—C6	1.396 (4)
O2—H2	0.8200	C5—H5	0.9300
O3—N4	1.246 (3)	C11—H11A	0.9600
O4—N4	1.210 (3)	C11—H11B	0.9600
N4—C15	1.435 (3)	C11—H11C	0.9600
C13—C14	1.372 (3)	C6—H6	0.9300
C13—C18	1.404 (3)	C2—C3	1.385 (4)
C13—C12	1.469 (3)	C2—H2A	0.9300
C12—H12	0.9300	C10—H10A	0.9600
C8—C9	1.369 (3)	C10—H10B	0.9600
C8—C7	1.445 (3)	C10—H10C	0.9600
C9—C10	1.490 (4)	C4—C3	1.366 (4)
C15—C16	1.394 (4)	C4—H4A	0.9300
C15—C14	1.398 (3)	C3—H3A	0.9300

C12—N3—C8	122.3 (2)	C17—C18—H18	119.3
C9—N1—N2	106.88 (19)	C13—C18—H18	119.3
C9—N1—C11	123.0 (2)	C18—C17—C16	121.0 (2)
N2—N1—C11	117.86 (19)	C18—C17—H17	119.5
N1—N2—C7	109.80 (19)	C16—C17—H17	119.5
N1—N2—C1	119.56 (19)	C4—C5—C6	120.4 (3)
C7—N2—C1	124.3 (2)	C4—C5—H5	119.8
C16—O2—H2	109.5	C6—C5—H5	119.8
O4—N4—O3	120.8 (3)	N1—C11—H11A	109.5
O4—N4—C15	119.4 (2)	N1—C11—H11B	109.5
O3—N4—C15	119.8 (3)	H11A—C11—H11B	109.5
C14—C13—C18	118.4 (2)	N1—C11—H11C	109.5
C14—C13—C12	121.3 (2)	H11A—C11—H11C	109.5
C18—C13—C12	120.3 (2)	H11B—C11—H11C	109.5
N3—C12—C13	119.4 (2)	C1—C6—C5	119.6 (3)
N3—C12—H12	120.3	C1—C6—H6	120.2
C13—C12—H12	120.3	C5—C6—H6	120.2
C9—C8—N3	121.5 (2)	O1—C7—N2	123.9 (2)
C9—C8—C7	108.8 (2)	O1—C7—C8	132.3 (2)
N3—C8—C7	129.6 (2)	N2—C7—C8	103.8 (2)
N1—C9—C8	110.2 (2)	C3—C2—C1	119.3 (3)
N1—C9—C10	121.8 (2)	C3—C2—H2A	120.3
C8—C9—C10	128.0 (2)	C1—C2—H2A	120.3
C16—C15—C14	121.5 (2)	C9—C10—H10A	109.5
C16—C15—N4	120.5 (2)	C9—C10—H10B	109.5
C14—C15—N4	118.0 (2)	H10A—C10—H10B	109.5
C13—C14—C15	120.1 (2)	C9—C10—H10C	109.5
C13—C14—H14	119.9	H10A—C10—H10C	109.5
C15—C14—H14	119.9	H10B—C10—H10C	109.5
O2—C16—C17	117.3 (2)	C3—C4—C5	119.7 (3)
O2—C16—C15	125.0 (2)	C3—C4—H4A	120.1
C17—C16—C15	117.7 (2)	C5—C4—H4A	120.1
C6—C1—C2	120.2 (2)	C4—C3—C2	120.8 (3)
C6—C1—N2	118.8 (2)	C4—C3—H3A	119.6
C2—C1—N2	121.0 (2)	C2—C3—H3A	119.6
C17—C18—C13	121.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.88	2.583 (3)	143
C12—H12···O1	0.93	2.45	3.096 (3)	127
C18—H18···O4ⁱ	0.93	2.38	3.079 (4)	132

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₄O₄
M_r	352.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.5000 (15), 7.8000 (16), 28.900 (6)
β (°)	95.00 (3)
V (Å³)	1684.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.29 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.971, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12221, 3012, 1762
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.160, 0.83
No. of reflections	3012
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.88	2.583 (3)	143
C12—H12···O1	0.93	2.45	3.096 (3)	127
C18—H18···O4ⁱ	0.93	2.38	3.079 (4)	132

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors are grateful to the Natural Science Foundation of Zhejiang Province (No. Y407081) for financial support.

References

Alemi, A. A. & Shaabani, B. (2000). Acta Chim. Slov. 47, 363–369. CAS Google Scholar
Bruker (1998). SMART. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Kim, G. J. & Shin, J. H. (1999). Catal. Lett. 63, 83–89. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yan, G.-B., Yang, M.-H. & Zheng, Y.-F. (2006). Acta Cryst. E62, m3481–m3482. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Y.-F., Yan, G.-B. & Gu, Y.-B. (2006). Acta Cryst. E62, o5134–o5135. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1988

doi:10.1107/S1600536808030031

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

(E)-4-(4-Hydr­­oxy-3-nitro­benzyl­­idene­amino)-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-4-(4-Hydroxy-3-nitrobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one