1,5-Dimethyl-4-[(E)-3-phenoxy­benzyl­ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Sun, Y.-F.; Zhang, F.-Y.; Liu, Y.; Wang, Z.-Y.; Cheng, X.-L.

doi:10.1107/S1600536808024409

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1679

doi:10.1107/S1600536808024409

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1,5-Dimethyl-4-[(E)-3-phenoxybenzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Yi-Feng Sun,^a ^* Feng-Yu Zhang,^b Yang Liu,^b Zi-Ying Wang ^a and Xue-Li Cheng ^a

^aDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^bLibrary, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: sunyf50@hotmail.com

(Received 30 July 2008; accepted 30 July 2008; online 6 August 2008)

The title Schiff base, C₂₄H₂₁N₃O₂, adopts an E configuration with respect to the central C=N bond. The pyrazole ring and the central benzene ring attached to the imino group are almost coplanar. The phenyl ring attached to the pyrazole unit is twisted by 39.3 (2)° with respect to the pyrazole ring plane. The phenoxy benzene ring makes a dihedral angle of 79.8 (2)° with the central benzene ring.

Related literature

For related crystal structures, see: Sun et al. (2007a ,b ,c ).

Experimental

Crystal data

C₂₄H₂₁N₃O₂
M_r = 383.44
Triclinic, $[P \overline 1]$
a = 7.6640 (12) Å
b = 8.3593 (14) Å
c = 16.731 (3) Å
α = 77.396 (3)°
β = 77.587 (2)°
γ = 76.240 (3)°
V = 1000.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.990
5300 measured reflections
3505 independent reflections
2584 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.04
3505 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 global, I. DOI: 10.1107/S1600536808024409/fj2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024409/fj2143Isup2.hkl

checkCIF report

Comment top

Antipyrine (2,3-dimethyl-1-phenylpyrazol-5-one) and its derivatives have been long known for their wide spectrum of biological activities. As part of our ongoing studies of antipyrine derivatives, the title compound, (I), has been prepared and its crystal structure is reported here (Fig. 1).

The molecule adopts an E configuration with respect to the central C=N double bond (Fig. 1).The pyrazole ring (N1/N2/C7—C9), the C13—C18 phenyl ring and the imino group are almost coplanar which allows conjugation. But the C1—C6 phenyl ring is twisted with respect to the central pyrazole ring plane by 39.3 (2)°. In addition, the mean planes of the C13—C18 and C19—C24 phenyl rings make a dihedral angle of 79.8 (2)°. Therefore the molecule is not planar. The bond distances and angles agree with the corresponding values found in similar compounds (Sun et al., 2007a,b,c).

Related literature top

For related crystal structures, see: Sun et al. (2007a,b,c).

Experimental top

A mixture of 4-aminoantipyrine (1 mmol) and 3-phenoxybenzaldehyde (1 mmol) in anhydrous ethanol (20 ml) was refluxed for 3 hr, and then cooled to room temperature. After cooling, the solvent was removed under reduced pressure and the solid residue was recrystallized from ethanol to yield the pure product(66% yield). m.p. 425–427 K. A single-crystal suitable for an X-ray structural analysis was obtained by slowly evaporating a ethanolic solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.

1,5-Dimethyl-4-[(E)-3-phenoxybenzylideneamino]-2-phenyl-1H- pyrazol-3(2H)-one top

Crystal data top

C₂₄H₂₁N₃O₂	Z = 2
M_r = 383.44	F(000) = 404
Triclinic, P1	D_x = 1.272 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6640 (12) Å	Cell parameters from 1817 reflections
b = 8.3593 (14) Å	θ = 2–25.1°
c = 16.731 (3) Å	µ = 0.08 mm⁻¹
α = 77.396 (3)°	T = 273 K
β = 77.587 (2)°	Block, colorless
γ = 76.240 (3)°	0.18 × 0.16 × 0.12 mm
V = 1000.9 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3505 independent reflections
Radiation source: fine-focus sealed tube	2584 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.985, T_max = 0.990	k = −9→8
5300 measured reflections	l = −19→19

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0553P)² + 0.1379P] where P = (F_o² + 2F_c²)/3
3505 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₁N₃O₂	γ = 76.240 (3)°
M_r = 383.44	V = 1000.9 (3) Å³
Triclinic, P1	Z = 2
a = 7.6640 (12) Å	Mo Kα radiation
b = 8.3593 (14) Å	µ = 0.08 mm⁻¹
c = 16.731 (3) Å	T = 273 K
α = 77.396 (3)°	0.18 × 0.16 × 0.12 mm
β = 77.587 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3505 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2584 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.990	R_int = 0.016
5300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
3505 reflections	Δρ_min = −0.18 e Å⁻³
264 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	−0.09698 (15)	0.55049 (16)	1.14179 (8)	0.0559 (3)
O2	−0.41493 (16)	1.0621 (2)	0.79039 (8)	0.0727 (4)
N1	0.17090 (17)	0.46344 (17)	1.19591 (8)	0.0451 (4)
N2	0.34291 (17)	0.50949 (17)	1.17773 (9)	0.0436 (3)
N3	0.15472 (18)	0.75399 (18)	1.00126 (8)	0.0463 (4)
C1	0.1017 (2)	0.3971 (2)	1.27873 (10)	0.0436 (4)
C2	0.1611 (2)	0.4293 (2)	1.34520 (11)	0.0534 (5)
H2	0.2455	0.4978	1.3359	0.064*
C3	0.0942 (3)	0.3590 (3)	1.42535 (12)	0.0644 (6)
H3	0.1348	0.3798	1.4699	0.077*
C4	−0.0311 (3)	0.2590 (3)	1.43974 (13)	0.0696 (6)
H4	−0.0752	0.2118	1.4938	0.084*
C5	−0.0915 (3)	0.2288 (3)	1.37361 (13)	0.0641 (5)
H5	−0.1778	0.1620	1.3833	0.077*
C6	−0.0253 (2)	0.2967 (2)	1.29318 (11)	0.0507 (4)
H6	−0.0659	0.2749	1.2488	0.061*
C7	0.0644 (2)	0.5536 (2)	1.13636 (10)	0.0430 (4)
C8	0.1860 (2)	0.6450 (2)	1.07513 (10)	0.0412 (4)
C9	0.3485 (2)	0.6120 (2)	1.10112 (10)	0.0431 (4)
C10	0.5167 (2)	0.6735 (3)	1.05804 (11)	0.0573 (5)
H10A	0.6070	0.5828	1.0386	0.086*
H10B	0.5625	0.7175	1.0960	0.086*
H10C	0.4894	0.7600	1.0117	0.086*
C11	0.4972 (2)	0.3701 (2)	1.19262 (13)	0.0607 (5)
H11A	0.5038	0.2889	1.1588	0.091*
H11B	0.4801	0.3187	1.2502	0.091*
H11C	0.6084	0.4116	1.1786	0.091*
C12	0.0019 (2)	0.7838 (2)	0.97743 (10)	0.0477 (4)
H12	−0.0906	0.7318	1.0099	0.057*
C13	−0.0321 (2)	0.8980 (2)	0.90021 (10)	0.0442 (4)
C14	0.1005 (2)	0.9784 (2)	0.84859 (11)	0.0502 (4)
H14	0.2152	0.9607	0.8628	0.060*
C15	0.0622 (2)	1.0844 (2)	0.77623 (12)	0.0548 (5)
H15	0.1519	1.1379	0.7420	0.066*
C16	−0.1063 (2)	1.1126 (2)	0.75369 (11)	0.0493 (4)
H16	−0.1304	1.1832	0.7044	0.059*
C17	−0.2385 (2)	1.0347 (2)	0.80524 (11)	0.0474 (4)
C18	−0.2022 (2)	0.9280 (2)	0.87751 (11)	0.0492 (4)
H18	−0.2927	0.8753	0.9115	0.059*
C19	−0.4469 (2)	1.1295 (2)	0.71019 (11)	0.0482 (4)
C20	−0.3803 (3)	1.0387 (3)	0.64795 (13)	0.0618 (5)
H20	−0.3083	0.9324	0.6586	0.074*
C21	−0.4186 (3)	1.1025 (3)	0.57065 (14)	0.0781 (7)
H21	−0.3719	1.0402	0.5283	0.094*
C22	−0.5239 (3)	1.2556 (4)	0.55469 (15)	0.0885 (8)
H22	−0.5492	1.2985	0.5013	0.106*
C23	−0.5939 (3)	1.3483 (3)	0.61630 (18)	0.0836 (7)
H23	−0.6673	1.4536	0.6049	0.100*
C24	−0.5555 (3)	1.2854 (2)	0.69626 (14)	0.0621 (5)
H24	−0.6020	1.3472	0.7388	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0386 (7)	0.0680 (9)	0.0613 (8)	−0.0141 (6)	−0.0158 (6)	−0.0009 (6)
O2	0.0417 (7)	0.1136 (12)	0.0539 (8)	−0.0163 (7)	−0.0152 (6)	0.0112 (8)
N1	0.0369 (7)	0.0496 (9)	0.0479 (9)	−0.0084 (6)	−0.0113 (6)	−0.0030 (7)
N2	0.0319 (7)	0.0491 (8)	0.0488 (8)	−0.0050 (6)	−0.0119 (6)	−0.0051 (7)
N3	0.0424 (8)	0.0543 (9)	0.0427 (8)	−0.0071 (7)	−0.0114 (6)	−0.0085 (7)
C1	0.0398 (9)	0.0379 (9)	0.0476 (10)	0.0016 (7)	−0.0093 (7)	−0.0046 (7)
C2	0.0522 (10)	0.0498 (11)	0.0575 (12)	−0.0003 (9)	−0.0169 (9)	−0.0114 (9)
C3	0.0641 (12)	0.0728 (14)	0.0502 (12)	0.0075 (11)	−0.0153 (10)	−0.0160 (10)
C4	0.0636 (13)	0.0783 (15)	0.0484 (12)	0.0006 (12)	−0.0003 (10)	0.0024 (10)
C5	0.0561 (11)	0.0622 (13)	0.0640 (14)	−0.0119 (10)	0.0010 (10)	−0.0012 (10)
C6	0.0458 (10)	0.0500 (11)	0.0527 (11)	−0.0052 (8)	−0.0071 (8)	−0.0078 (8)
C7	0.0376 (9)	0.0453 (10)	0.0469 (10)	−0.0037 (7)	−0.0125 (7)	−0.0097 (8)
C8	0.0369 (8)	0.0476 (10)	0.0400 (9)	−0.0061 (7)	−0.0095 (7)	−0.0092 (7)
C9	0.0386 (9)	0.0492 (10)	0.0419 (9)	−0.0071 (7)	−0.0074 (7)	−0.0103 (8)
C10	0.0409 (10)	0.0769 (14)	0.0537 (11)	−0.0155 (9)	−0.0075 (8)	−0.0070 (10)
C11	0.0441 (10)	0.0598 (12)	0.0742 (13)	0.0031 (9)	−0.0205 (9)	−0.0080 (10)
C12	0.0426 (9)	0.0555 (11)	0.0445 (10)	−0.0105 (8)	−0.0102 (8)	−0.0044 (8)
C13	0.0422 (9)	0.0477 (10)	0.0437 (10)	−0.0073 (8)	−0.0109 (7)	−0.0089 (8)
C14	0.0398 (9)	0.0562 (11)	0.0568 (11)	−0.0123 (8)	−0.0131 (8)	−0.0070 (9)
C15	0.0497 (10)	0.0565 (12)	0.0590 (12)	−0.0211 (9)	−0.0095 (9)	−0.0004 (9)
C16	0.0508 (10)	0.0451 (10)	0.0497 (10)	−0.0113 (8)	−0.0128 (8)	0.0020 (8)
C17	0.0378 (9)	0.0568 (11)	0.0470 (10)	−0.0085 (8)	−0.0112 (8)	−0.0050 (8)
C18	0.0429 (9)	0.0589 (11)	0.0449 (10)	−0.0142 (8)	−0.0078 (8)	−0.0024 (8)
C19	0.0363 (9)	0.0573 (11)	0.0488 (11)	−0.0105 (8)	−0.0137 (8)	0.0028 (8)
C20	0.0598 (12)	0.0541 (12)	0.0644 (13)	−0.0029 (9)	−0.0083 (10)	−0.0070 (10)
C21	0.0711 (14)	0.1030 (19)	0.0636 (15)	−0.0168 (14)	−0.0149 (12)	−0.0192 (13)
C22	0.0640 (14)	0.129 (2)	0.0611 (15)	−0.0159 (15)	−0.0246 (12)	0.0161 (15)
C23	0.0583 (13)	0.0630 (14)	0.108 (2)	0.0043 (11)	−0.0239 (13)	0.0230 (14)
C24	0.0521 (11)	0.0516 (12)	0.0806 (15)	−0.0063 (9)	−0.0097 (10)	−0.0134 (10)

Geometric parameters (Å, º) top

O1—C7	1.2264 (19)	C11—H11A	0.9600
O2—C17	1.383 (2)	C11—H11B	0.9600
O2—C19	1.387 (2)	C11—H11C	0.9600
N1—C7	1.399 (2)	C12—C13	1.462 (2)
N1—N2	1.4130 (18)	C12—H12	0.9300
N1—C1	1.413 (2)	C13—C18	1.386 (2)
N2—C9	1.376 (2)	C13—C14	1.387 (2)
N2—C11	1.471 (2)	C14—C15	1.378 (2)
N3—C12	1.269 (2)	C14—H14	0.9300
N3—C8	1.395 (2)	C15—C16	1.376 (2)
C1—C6	1.382 (2)	C15—H15	0.9300
C1—C2	1.386 (2)	C16—C17	1.374 (2)
C2—C3	1.382 (3)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.375 (2)
C3—C4	1.369 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.362 (3)
C4—C5	1.379 (3)	C19—C24	1.371 (3)
C4—H4	0.9300	C20—C21	1.353 (3)
C5—C6	1.379 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.346 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.445 (2)	C22—C23	1.366 (4)
C8—C9	1.354 (2)	C22—H22	0.9300
C9—C10	1.483 (2)	C23—C24	1.393 (3)
C10—H10A	0.9600	C23—H23	0.9300
C10—H10B	0.9600	C24—H24	0.9300
C10—H10C	0.9600

C17—O2—C19	118.13 (13)	H11A—C11—H11B	109.5
C7—N1—N2	110.26 (13)	N2—C11—H11C	109.5
C7—N1—C1	125.01 (13)	H11A—C11—H11C	109.5
N2—N1—C1	119.24 (13)	H11B—C11—H11C	109.5
C9—N2—N1	105.45 (12)	N3—C12—C13	121.58 (17)
C9—N2—C11	119.28 (14)	N3—C12—H12	119.2
N1—N2—C11	114.71 (14)	C13—C12—H12	119.2
C12—N3—C8	121.20 (15)	C18—C13—C14	118.58 (16)
C6—C1—C2	119.78 (17)	C18—C13—C12	119.30 (16)
C6—C1—N1	119.10 (15)	C14—C13—C12	122.11 (15)
C2—C1—N1	121.11 (16)	C15—C14—C13	120.02 (16)
C3—C2—C1	119.65 (19)	C15—C14—H14	120.0
C3—C2—H2	120.2	C13—C14—H14	120.0
C1—C2—H2	120.2	C16—C15—C14	121.13 (17)
C4—C3—C2	120.64 (19)	C16—C15—H15	119.4
C4—C3—H3	119.7	C14—C15—H15	119.4
C2—C3—H3	119.7	C17—C16—C15	118.93 (17)
C3—C4—C5	119.6 (2)	C17—C16—H16	120.5
C3—C4—H4	120.2	C15—C16—H16	120.5
C5—C4—H4	120.2	C16—C17—C18	120.61 (16)
C6—C5—C4	120.6 (2)	C16—C17—O2	123.25 (16)
C6—C5—H5	119.7	C18—C17—O2	116.10 (16)
C4—C5—H5	119.7	C17—C18—C13	120.72 (17)
C5—C6—C1	119.70 (18)	C17—C18—H18	119.6
C5—C6—H6	120.1	C13—C18—H18	119.6
C1—C6—H6	120.1	C20—C19—C24	120.94 (18)
O1—C7—N1	123.73 (16)	C20—C19—O2	120.53 (17)
O1—C7—C8	131.93 (16)	C24—C19—O2	118.42 (17)
N1—C7—C8	104.32 (14)	C21—C20—C19	120.2 (2)
C9—C8—N3	121.71 (15)	C21—C20—H20	119.9
C9—C8—C7	108.38 (15)	C19—C20—H20	119.9
N3—C8—C7	129.89 (14)	C22—C21—C20	120.4 (2)
C8—C9—N2	111.07 (15)	C22—C21—H21	119.8
C8—C9—C10	128.06 (16)	C20—C21—H21	119.8
N2—C9—C10	120.86 (14)	C21—C22—C23	120.5 (2)
C9—C10—H10A	109.5	C21—C22—H22	119.8
C9—C10—H10B	109.5	C23—C22—H22	119.8
H10A—C10—H10B	109.5	C22—C23—C24	120.1 (2)
C9—C10—H10C	109.5	C22—C23—H23	120.0
H10A—C10—H10C	109.5	C24—C23—H23	120.0
H10B—C10—H10C	109.5	C19—C24—C23	117.9 (2)
N2—C11—H11A	109.5	C19—C24—H24	121.1
N2—C11—H11B	109.5	C23—C24—H24	121.1

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁N₃O₂
M_r	383.44
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.6640 (12), 8.3593 (14), 16.731 (3)
α, β, γ (°)	77.396 (3), 77.587 (2), 76.240 (3)
V (Å³)	1000.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	5300, 3505, 2584
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.04
No. of reflections	3505
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Foundation of Taishan University.

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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