1,5-Dimethyl-4-[(5-methyl-2-furyl)­methyl­ene­amino]-2-phenyl-1H-pyrazol-3(2H)-one

Guo, Y.

doi:10.1107/S1600536808015419

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1170

doi:10.1107/S1600536808015419

Open

access

1,5-Dimethyl-4-[(5-methyl-2-furyl)methyleneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Yaning Guo ^a ^*

^aDepartment of Chemistry, Baoji University of Arts and Science, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: ggyn1997@163.com

(Received 6 May 2008; accepted 22 May 2008; online 30 May 2008)

In the title compound, C₁₇H₁₇N₃O₂, a derivative of 4-aminoantipyrine, the structure displays a trans configuration with respect to the imine C=N double bond. The pyrazoline ring is essentially planar and makes a dihedral angle of 55.80 (1)° with the phenyl ring.

Related literature

For related literature, see: Ali et al. (2002 ); Allen et al. (1987 ); Carlton et al. (1995 ); Coolen et al. (1999 ); Cukurovali et al. (2002 ); Greisen & Andreasen (1976 ); Jiang et al. (2000 ); Liang et al. (2002 ); Tarafder et al. (2002 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₂
M_r = 295.34
Monoclinic, P 2₁ /c
a = 11.811 (7) Å
b = 9.997 (6) Å
c = 14.116 (9) Å
β = 110.963 (9)°
V = 1556.4 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.967, T_max = 0.967
5012 measured reflections
2670 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.154
S = 1.07
2670 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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/S1600536808015419/bq2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015419/bq2080Isup2.hkl

checkCIF report

Comment top

In recent years, the role of antipyrine and antipyridine derivatives in biological processes have become a topic of study (Carlton et al., 1995; Coolen et al., 1999; Jiang et al., 2000). Antipyrine is an antipyretic drug that is still being used to measure the total hepatic oxidase activity. The properties of antipyrine make it a suitable marker for oxidative stress (Greisen & Andereasen, 1976). Schiff base ligands have demonstrated significant biological activities and new examples are being tested for their antitumor, antimicrobial and antiviral activities (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). These properties stimulated our interest in this field. Crystals of the title compound, (I), were obtained as a new antipyrine Schiff base compound.

The perspective view of the structure and a packing diagram of (I) are illustrated in Fig.1 and 2, respectively. All the bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those observed in a similar antipyrine Schiff base (Liang et al., 2002). As seen from Fig. 1, the pyrazoline ring is essentially planar. Atom O2 deviates from the pyrazoline mean plane by -0.117 (5) Å, whereas atoms C10 and C11 by 0.115 (7) and 0.582 (7) Å, on the same side. The dihedral angle between the pyrazoline ring and the C12—C17 phenyl ring is 55.80 (1) °. The furan ring and the pyrazoline ring are approximately coplanar with the dihedral angle between them of 4.79 (2) °. As expected, the molecular structure adopts a trans configuration about the C6═N1 bond.

Related literature top

For related literature, see: Ali et al. (2002); Allen et al. (1987); Carlton et al. (1995); Coolen et al. (1999); Cukurovali et al. (2002); Greisen & Andereasen (1976); Jiang et al. (2000); Liang et al. (2002); Tarafder et al. (2002).

Experimental top

A mixture of 5-methyl-2-furaldehyd (0.1 mmol, 11.0 mg) and 4-aminoantipyrine (0.1 mmol, 20.3 mg) was dissolved in 10 ml methanol, and stirred for about 30 min at room temperature to give a clear yellow solution. After keeping this solution in air for 7 d, yellow block crystals were formed at the bottom of vessel by slowly evaporating the solvent.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 the title compound in 30% probability ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. The molecular packing of (I) viewed along the b-axis.

1,5-Dimethyl-4-[(5-methyl-2-furyl)methyleneamino]-2-phenyl-1H-pyrazol- 3(2H)-one top

Crystal data top

C₁₇H₁₇N₃O₂	F(000) = 624
M_r = 295.34	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3656 reflections
a = 11.811 (7) Å	θ = 2.6–27.1°
b = 9.997 (6) Å	µ = 0.09 mm⁻¹
c = 14.116 (9) Å	T = 296 K
β = 110.963 (9)°	Block, yellow
V = 1556.4 (16) Å³	0.40 × 0.40 × 0.40 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2670 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −4→14
T_min = 0.967, T_max = 0.967	k = −11→9
5012 measured reflections	l = −16→16

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)] = 0.066	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0438P)² + 0.5447P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2670 reflections	Δρ_max = 0.17 e Å⁻³
203 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (4)

Crystal data top

C₁₇H₁₇N₃O₂	V = 1556.4 (16) Å³
M_r = 295.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.811 (7) Å	µ = 0.09 mm⁻¹
b = 9.997 (6) Å	T = 296 K
c = 14.116 (9) Å	0.40 × 0.40 × 0.40 mm
β = 110.963 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2670 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1904 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.967	R_int = 0.097
5012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
2670 reflections	Δρ_min = −0.17 e Å⁻³
203 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
O1	0.46426 (15)	−0.0177 (2)	0.11946 (13)	0.0512 (6)
O2	0.10583 (17)	0.3027 (2)	0.15207 (15)	0.0696 (7)
N1	0.23169 (19)	0.0950 (2)	0.05296 (15)	0.0455 (6)
N2	−0.07371 (19)	0.1894 (2)	−0.08553 (15)	0.0486 (6)
N3	−0.05032 (19)	0.2766 (3)	−0.00250 (16)	0.0519 (7)
C7	0.1172 (2)	0.1547 (3)	0.01786 (18)	0.0433 (7)
C1	0.5813 (2)	−0.0571 (3)	0.1754 (2)	0.0488 (7)
C8	0.0317 (2)	0.1251 (3)	−0.07436 (18)	0.0449 (7)
C10	0.0408 (3)	0.0357 (3)	−0.15564 (19)	0.0576 (8)
H4A	0.0415	0.0887	−0.2121	0.086*
H4B	−0.0275	−0.0238	−0.1773	0.086*
H4C	0.1143	−0.0154	−0.1299	0.086*
C6	0.3099 (2)	0.1276 (3)	0.1398 (2)	0.0547 (8)
H5	0.2884	0.1906	0.1788	0.066*
C9	0.0665 (2)	0.2508 (3)	0.0669 (2)	0.0486 (7)
C2	0.6170 (3)	0.0008 (4)	0.2668 (2)	0.0621 (9)
H7	0.6913	−0.0110	0.3191	0.075*
C12	−0.1484 (3)	0.3267 (3)	0.02341 (19)	0.0511 (8)
C4	0.4294 (2)	0.0702 (3)	0.1788 (2)	0.0525 (8)
C13	−0.2464 (3)	0.2472 (4)	0.0175 (2)	0.0605 (9)
H10	−0.2509	0.1595	−0.0054	0.073*
C3	0.5208 (3)	0.0835 (4)	0.2690 (2)	0.0704 (10)
H11	0.5206	0.1371	0.3227	0.084*
C15	−0.3310 (4)	0.4306 (5)	0.0795 (3)	0.0885 (14)
H12	−0.3929	0.4662	0.0978	0.106*
C17	−0.1411 (3)	0.4580 (4)	0.0576 (2)	0.0673 (9)
H13	−0.0750	0.5113	0.0615	0.081*
C5	0.6407 (3)	−0.1481 (4)	0.1252 (2)	0.0652 (9)
H14A	0.7193	−0.1726	0.1722	0.098*
H14B	0.6492	−0.1038	0.0678	0.098*
H14C	0.5921	−0.2270	0.1029	0.098*
C11	−0.1602 (3)	0.2351 (4)	−0.1828 (2)	0.0852 (13)
H15A	−0.1321	0.3176	−0.2015	0.128*
H15B	−0.2378	0.2492	−0.1769	0.128*
H15C	−0.1675	0.1688	−0.2338	0.128*
C14	−0.3378 (3)	0.2996 (5)	0.0461 (2)	0.0763 (11)
H16	−0.4039	0.2468	0.0429	0.092*
C16	−0.2332 (4)	0.5077 (4)	0.0854 (3)	0.0879 (13)
H17	−0.2288	0.5953	0.1086	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0387 (11)	0.0633 (14)	0.0496 (10)	0.0038 (10)	0.0134 (8)	−0.0004 (10)
O2	0.0511 (13)	0.0848 (17)	0.0624 (13)	0.0078 (12)	0.0077 (10)	−0.0311 (12)
N1	0.0359 (13)	0.0542 (16)	0.0473 (12)	−0.0030 (11)	0.0159 (10)	−0.0022 (11)
N2	0.0441 (14)	0.0550 (16)	0.0423 (12)	0.0061 (12)	0.0099 (10)	−0.0064 (11)
N3	0.0401 (13)	0.0561 (16)	0.0545 (13)	0.0049 (12)	0.0106 (10)	−0.0120 (12)
C7	0.0361 (15)	0.0492 (18)	0.0442 (14)	−0.0031 (13)	0.0139 (11)	−0.0025 (13)
C1	0.0309 (15)	0.057 (2)	0.0583 (16)	0.0012 (13)	0.0153 (12)	0.0114 (14)
C8	0.0445 (16)	0.0485 (18)	0.0441 (14)	−0.0002 (14)	0.0186 (12)	0.0029 (13)
C10	0.0570 (19)	0.067 (2)	0.0473 (15)	0.0056 (17)	0.0167 (13)	−0.0030 (15)
C6	0.0446 (17)	0.065 (2)	0.0531 (16)	0.0048 (15)	0.0158 (13)	−0.0141 (15)
C9	0.0405 (16)	0.0509 (18)	0.0517 (15)	0.0003 (14)	0.0130 (12)	−0.0094 (14)
C2	0.0388 (16)	0.073 (2)	0.0631 (18)	−0.0015 (17)	0.0039 (13)	−0.0026 (17)
C12	0.0445 (17)	0.054 (2)	0.0485 (15)	0.0101 (15)	0.0083 (12)	0.0002 (14)
C4	0.0373 (16)	0.062 (2)	0.0562 (16)	−0.0004 (14)	0.0146 (13)	−0.0091 (15)
C13	0.0462 (18)	0.067 (2)	0.0596 (17)	0.0060 (17)	0.0080 (14)	−0.0076 (16)
C3	0.0514 (19)	0.086 (3)	0.0624 (18)	0.0040 (19)	0.0064 (15)	−0.0222 (18)
C15	0.060 (2)	0.128 (4)	0.076 (2)	0.039 (3)	0.0220 (18)	−0.011 (2)
C17	0.068 (2)	0.055 (2)	0.076 (2)	0.0100 (18)	0.0231 (17)	−0.0030 (17)
C5	0.0510 (18)	0.081 (3)	0.0661 (18)	0.0154 (18)	0.0237 (15)	0.0138 (18)
C11	0.084 (2)	0.101 (3)	0.0503 (17)	0.032 (2)	−0.0009 (17)	−0.0012 (19)
C14	0.0406 (19)	0.113 (4)	0.069 (2)	0.010 (2)	0.0120 (15)	−0.005 (2)
C16	0.097 (3)	0.075 (3)	0.090 (3)	0.035 (3)	0.030 (2)	−0.009 (2)

Geometric parameters (Å, º) top

O1—C4	1.375 (3)	C2—H7	0.9300
O1—C1	1.382 (3)	C12—C13	1.382 (4)
O2—C9	1.237 (3)	C12—C17	1.390 (4)
N1—C6	1.285 (3)	C4—C3	1.349 (4)
N1—C7	1.397 (3)	C13—C14	1.383 (5)
N2—C8	1.359 (3)	C13—H10	0.9300
N2—N3	1.407 (3)	C3—H11	0.9300
N2—C11	1.461 (3)	C15—C16	1.366 (6)
N3—C9	1.401 (3)	C15—C14	1.384 (6)
N3—C12	1.424 (4)	C15—H12	0.9300
C7—C8	1.364 (3)	C17—C16	1.375 (5)
C7—C9	1.435 (4)	C17—H13	0.9300
C1—C2	1.337 (4)	C5—H14A	0.9600
C1—C5	1.475 (4)	C5—H14B	0.9600
C8—C10	1.488 (4)	C5—H14C	0.9600
C10—H4A	0.9600	C11—H15A	0.9600
C10—H4B	0.9600	C11—H15B	0.9600
C10—H4C	0.9600	C11—H15C	0.9600
C6—C4	1.438 (4)	C14—H16	0.9300
C6—H5	0.9300	C16—H17	0.9300
C2—C3	1.414 (4)

C4—O1—C1	106.9 (2)	C17—C12—N3	117.8 (3)
C6—N1—C7	120.3 (2)	C3—C4—O1	109.0 (3)
C8—N2—N3	107.33 (19)	C3—C4—C6	131.8 (3)
C8—N2—C11	124.1 (2)	O1—C4—C6	119.2 (2)
N3—N2—C11	116.8 (2)	C12—C13—C14	119.3 (3)
C9—N3—N2	108.6 (2)	C12—C13—H10	120.4
C9—N3—C12	124.9 (2)	C14—C13—H10	120.4
N2—N3—C12	119.8 (2)	C4—C3—C2	107.5 (3)
C8—C7—N1	122.5 (2)	C4—C3—H11	126.3
C8—C7—C9	108.2 (2)	C2—C3—H11	126.3
N1—C7—C9	129.3 (2)	C16—C15—C14	120.0 (4)
C2—C1—O1	109.5 (3)	C16—C15—H12	120.0
C2—C1—C5	133.7 (3)	C14—C15—H12	120.0
O1—C1—C5	116.8 (2)	C16—C17—C12	118.9 (4)
N2—C8—C7	110.0 (2)	C16—C17—H13	120.5
N2—C8—C10	120.7 (2)	C12—C17—H13	120.5
C7—C8—C10	129.3 (3)	C1—C5—H14A	109.5
C8—C10—H4A	109.5	C1—C5—H14B	109.5
C8—C10—H4B	109.5	H14A—C5—H14B	109.5
H4A—C10—H4B	109.5	C1—C5—H14C	109.5
C8—C10—H4C	109.5	H14A—C5—H14C	109.5
H4A—C10—H4C	109.5	H14B—C5—H14C	109.5
H4B—C10—H4C	109.5	N2—C11—H15A	109.5
N1—C6—C4	122.4 (3)	N2—C11—H15B	109.5
N1—C6—H5	118.8	H15A—C11—H15B	109.5
C4—C6—H5	118.8	N2—C11—H15C	109.5
O2—C9—N3	122.4 (3)	H15A—C11—H15C	109.5
O2—C9—C7	132.3 (2)	H15B—C11—H15C	109.5
N3—C9—C7	105.2 (2)	C13—C14—C15	120.1 (4)
C1—C2—C3	107.2 (3)	C13—C14—H16	120.0
C1—C2—H7	126.4	C15—C14—H16	120.0
C3—C2—H7	126.4	C15—C16—C17	121.1 (4)
C13—C12—C17	120.7 (3)	C15—C16—H17	119.5
C13—C12—N3	121.6 (3)	C17—C16—H17	119.5

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂
M_r	295.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.811 (7), 9.997 (6), 14.116 (9)
β (°)	110.963 (9)
V (Å³)	1556.4 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.967, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5012, 2670, 1904
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.154, 1.07
No. of reflections	2670
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is grateful for the support of a special research grant (No. 05jk136) of the Education Department of Shaanxi Province.

References

Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali, A. M. (2002). J. Inorg. Biochem. 92, 141–148. CSD CrossRef PubMed Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carlton, L. D., Schmith, V. D. & Brouwer, K. L. R. (1995). Prostaglandins, 50, 341–347. CrossRef CAS PubMed Web of Science Google Scholar
Coolen, S. A. J., Everaerts, F. M. & Huf, F. A. (1999). J. Chromatogr. B, 732, 103–113. CrossRef CAS Google Scholar
Cukurovali, A., Yilmaz, I., Özmen, H. & Ahmedzade, M. (2002). Transition Met. Chem. 27, 171–176. Web of Science CrossRef CAS Google Scholar
Greisen, G. & Andreasen, P. B. (1976). Acta Pharmacol. Toxicol. 38, 49–58. CrossRef CAS Google Scholar
Jiang, S. X., Bayón, J. E., Ferre, I., Mao, X. Z. & González-Gallego, J. (2000). Vet. Parasitology, 88, 177–186. Web of Science CrossRef CAS Google Scholar
Liang, H., Yu, Q. & Hu, R.-X. (2002). Transition Met. Chem. 27, 454–457. CAS Google Scholar
Sheldrick, G. M. (2000). 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
Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2547–2554. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.