4-({4-[1-(Methoxy­imino)eth­yl]anilino}(phen­yl)methyl­ene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one

Yao, J.; Gao, S.-X.; Dong, W.-K.; Tong, J.-F.; Gong, S.-S.

doi:10.1107/S1600536809048326

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3122-o3123

doi:10.1107/S1600536809048326

Open

access

4-({4-[1-(Methoxyimino)ethyl]anilino}(phenyl)methylene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one

Jian Yao,^a Su-Xia Gao,^b Wen-Kui Dong,^a ^* Jun-Feng Tong ^a and Shang-Sheng Gong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bSchool of Environmental Science and Municipal Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@126.com

(Received 9 October 2009; accepted 14 November 2009; online 21 November 2009)

In the title compound, C₂₆H₂₄N₄O₂, the dihedral angles between the central pyrazole ring and the other three benzene rings are 40.02 (3), 77.51 (5) and 55.72 (3)°. A strong intramolecular N—H⋯O hydrogen bond forms a six-membered ring with an S(6) motif. In the crystal structure, a weak intermolecular C—H⋯N interaction with graph-set motif R₂²(8) and C—H⋯O hydrogen bonds link each molecule to three others, forming an infinite two-dimensional supramolecular structure.

Related literature

For background to 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, see: Lahiri et al. (2003 ). For related structures, see: Bomfim et al. (2005 ); Wang et al. (2008 ). For bond-length data, see: Allen et al. (1987 ). For graph-set notation, see: Bernstein et al. (1995 ). For the synthesis, see: Rafiq et al. (2008 ); Zhao et al. (2009 ); Dong et al. (2008 ).

Experimental

Crystal data

C₂₆H₂₄N₄O₂
M_r = 424.49
Triclinic, $[P \overline 1]$
a = 7.3550 (6) Å
b = 11.1609 (13) Å
c = 14.9700 (12) Å
α = 68.536 (1)°
β = 76.654 (2)°
γ = 76.182 (2)°
V = 1096.46 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.49 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.992
5654 measured reflections
3781 independent reflections
1861 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.246
S = 1.03
3781 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.86	1.95	2.683 (4)	142
C26—H26C⋯N4ⁱ	0.96	2.72	3.643 (9)	163
C9—H9⋯O1ⁱⁱ	0.93	2.67	3.398 (6)	135
Symmetry codes: (i) -x-1, -y, -z+1; (ii) x+1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536809048326/fl2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048326/fl2280Isup2.hkl

checkCIF report

Comment top

1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) is an efficient extractant of metal ions, and has the potential to form different types of compounds (Lahiri et al., 2003). Some structures of oxime compounds, similar to the title compound (Fig. 1), formed by Schiff base reactions have been reported (Bomfim et al., 2005; Wang et al., 2008).

The title compound is a potential tridentate mono-oxime ligand. The bond lengths and angles in the molecule are within normal ranges (Allen et al., 1987). In the molecule, the dihedral angles between the central pyrazole ring and the other three benzene rings (C5—C10), (C12—C17) and (C18—C23) are 40.02 (3)°, 77.51 (5)° and 55.72 (3)°, respectively.

In the crystal, a strong intramolecular N3—H3···O1 hydrogen bond forms a six-membered ring, producing a S(6) ring motif (Table 1, Fig. 1). A weak intermolecular C26—H26C···N4 interacation with the graph-set motif of R₂²(8) (Bernstein et al., 1995) and C9—H9···O1 hydrogen bonds, link each molecule to three others, forming an infinite two-dimensional supramolecular structure along the diagonal of the unit cell (Table 1, Fig. 2).

Related literature top

For background to 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, see: Lahiri et al. (2003). For related structures, see: Bomfim et al. (2005); Wang et al. (2008). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For the synthesis, see: Rafiq et al. (2008); Zhao et al. (2009); Dong et al. (2008).

Experimental top

1-(4-Aminophenyl)ethanone O-methyl oxime (I) was prepared using 1-(4-aminophenyl)ethanone and methoxyamine (Rafiq et al., 2008; Zhao et al., 2009). The title compound was prepared according to a previously reported procedure (Dong et al., 2008). To an ethanol solution (7 ml) of (I) (164.1 mg, 1.00 mmol) was added dropwise an ethanol solution (7 ml) of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (278.3 mg,1.00 mmol). The mixture was stirred at 333–338 K for 24 h. The solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound. Yield, 68.9%. m. p. 454–456 K. Anal. Calcd. for C₂₆H₂₄N₄O₂: C, 73.56; H, 5.70; N, 13.20. Found: C,73.63; H,5.81; N,13.07.

Pale-yellow block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of dichloromethane at room temperature over a period of approximately one month.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level. Intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. Part of two-dimensional supramolecular structure showing intermolecular hydrogen bonds interactions (dashed lines).

4-({4-[1-(Methoxyimino)ethyl]anilino}(phenyl)methylene)-3-methyl- 2-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₆H₂₄N₄O₂	Z = 2
M_r = 424.49	F(000) = 448
Triclinic, P1	D_x = 1.286 Mg m⁻³
Hall symbol: -P 1	Melting point = 454–456 K
a = 7.3550 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1609 (13) Å	Cell parameters from 1018 reflections
c = 14.9700 (12) Å	θ = 2.9–22.3°
α = 68.536 (1)°	µ = 0.08 mm⁻¹
β = 76.654 (2)°	T = 298 K
γ = 76.182 (2)°	Block-like, yellow
V = 1096.46 (18) Å³	0.50 × 0.49 × 0.10 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3781 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.960, T_max = 0.992	k = −13→13
5654 measured reflections	l = −12→17

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)] = 0.077	H-atom parameters constrained
wR(F²) = 0.246	w = 1/[σ²(F_o²) + (0.1078P)² + 0.3814P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3781 reflections	Δρ_max = 0.24 e Å⁻³
290 parameters	Δρ_min = −0.26 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: 0.014 (5)

Crystal data top

C₂₆H₂₄N₄O₂	γ = 76.182 (2)°
M_r = 424.49	V = 1096.46 (18) Å³
Triclinic, P1	Z = 2
a = 7.3550 (6) Å	Mo Kα radiation
b = 11.1609 (13) Å	µ = 0.08 mm⁻¹
c = 14.9700 (12) Å	T = 298 K
α = 68.536 (1)°	0.50 × 0.49 × 0.10 mm
β = 76.654 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3781 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1861 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.992	R_int = 0.037
5654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.246	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3781 reflections	Δρ_min = −0.26 e Å⁻³
290 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
N1	0.5909 (5)	0.6071 (3)	0.1299 (3)	0.0443 (10)
N2	0.6863 (5)	0.5101 (4)	0.0891 (3)	0.0476 (10)
N3	0.1377 (5)	0.4355 (4)	0.2977 (3)	0.0498 (11)
H3	0.1605	0.5047	0.3025	0.060*
N4	−0.5909 (6)	0.1833 (5)	0.5239 (3)	0.0646 (13)
O1	0.3193 (4)	0.6395 (3)	0.2404 (2)	0.0505 (9)
O2	−0.7474 (6)	0.1375 (4)	0.5927 (3)	0.0817 (13)
C1	0.4246 (6)	0.5767 (4)	0.1894 (3)	0.0403 (11)
C2	0.4103 (6)	0.4552 (4)	0.1810 (3)	0.0384 (11)
C3	0.5784 (7)	0.4221 (4)	0.1177 (3)	0.0449 (12)
C4	0.6428 (7)	0.3052 (5)	0.0868 (4)	0.0602 (15)
H4A	0.7660	0.3094	0.0477	0.090*
H4B	0.5548	0.3022	0.0495	0.090*
H4C	0.6494	0.2281	0.1431	0.090*
C5	0.6829 (6)	0.7119 (4)	0.1179 (3)	0.0406 (11)
C6	0.5761 (7)	0.8342 (5)	0.1089 (4)	0.0532 (13)
H6	0.4470	0.8489	0.1069	0.064*
C7	0.6606 (8)	0.9334 (5)	0.1030 (4)	0.0600 (15)
H7	0.5880	1.0155	0.0983	0.072*
C8	0.8494 (8)	0.9141 (6)	0.1040 (4)	0.0665 (16)
H8	0.9060	0.9825	0.0998	0.080*
C9	0.9571 (7)	0.7925 (6)	0.1112 (4)	0.0654 (16)
H9	1.0869	0.7792	0.1111	0.078*
C10	0.8737 (7)	0.6911 (5)	0.1184 (4)	0.0533 (14)
H10	0.9461	0.6089	0.1237	0.064*
C11	0.2609 (6)	0.3874 (4)	0.2346 (3)	0.0401 (11)
C12	0.2423 (6)	0.2628 (4)	0.2279 (3)	0.0422 (12)
C13	0.2792 (7)	0.1492 (5)	0.3045 (4)	0.0532 (13)
H13	0.3171	0.1517	0.3588	0.064*
C14	0.2592 (7)	0.0319 (5)	0.2996 (4)	0.0610 (15)
H14	0.2862	−0.0447	0.3506	0.073*
C15	0.2010 (7)	0.0263 (5)	0.2221 (4)	0.0613 (15)
H15	0.1853	−0.0529	0.2202	0.074*
C16	0.1653 (7)	0.1410 (5)	0.1456 (4)	0.0598 (15)
H16	0.1251	0.1385	0.0919	0.072*
C17	0.1881 (6)	0.2558 (5)	0.1483 (4)	0.0500 (13)
H17	0.1668	0.3313	0.0955	0.060*
C18	−0.0273 (6)	0.3889 (4)	0.3586 (3)	0.0408 (11)
C19	−0.0580 (7)	0.3782 (5)	0.4543 (4)	0.0500 (13)
H19	0.0328	0.3967	0.4792	0.060*
C20	−0.2214 (6)	0.3404 (4)	0.5147 (4)	0.0488 (13)
H20	−0.2408	0.3350	0.5796	0.059*
C21	−0.3560 (6)	0.3105 (4)	0.4794 (3)	0.0426 (12)
C22	−0.3236 (6)	0.3217 (4)	0.3821 (3)	0.0448 (12)
H22	−0.4128	0.3012	0.3574	0.054*
C23	−0.1635 (6)	0.3622 (4)	0.3211 (4)	0.0467 (12)
H23	−0.1463	0.3717	0.2555	0.056*
C24	−0.5294 (6)	0.2642 (4)	0.5452 (4)	0.0460 (12)
C25	−0.6082 (7)	0.3043 (6)	0.6314 (4)	0.0646 (15)
H25A	−0.7391	0.2944	0.6510	0.097*
H25B	−0.5983	0.3941	0.6161	0.097*
H25C	−0.5387	0.2506	0.6833	0.097*
C26	−0.7905 (10)	0.0306 (7)	0.5759 (6)	0.111 (3)
H26A	−0.8927	0.0611	0.5388	0.166*
H26B	−0.8271	−0.0336	0.6370	0.166*
H26C	−0.6806	−0.0079	0.5404	0.166*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.051 (2)	0.042 (2)	0.044 (2)	−0.0190 (19)	0.000 (2)	−0.0154 (19)
N2	0.050 (2)	0.053 (2)	0.041 (3)	−0.017 (2)	0.002 (2)	−0.017 (2)
N3	0.051 (2)	0.051 (2)	0.054 (3)	−0.027 (2)	0.005 (2)	−0.021 (2)
N4	0.053 (3)	0.090 (3)	0.056 (3)	−0.038 (2)	0.022 (2)	−0.031 (3)
O1	0.048 (2)	0.055 (2)	0.054 (2)	−0.0193 (16)	0.0039 (17)	−0.0249 (18)
O2	0.076 (3)	0.091 (3)	0.077 (3)	−0.041 (2)	0.017 (2)	−0.028 (2)
C1	0.043 (3)	0.051 (3)	0.032 (3)	−0.019 (2)	−0.005 (2)	−0.014 (2)
C2	0.043 (3)	0.043 (3)	0.031 (3)	−0.017 (2)	−0.002 (2)	−0.011 (2)
C3	0.051 (3)	0.050 (3)	0.039 (3)	−0.018 (2)	−0.005 (2)	−0.015 (2)
C4	0.060 (3)	0.059 (3)	0.067 (4)	−0.020 (3)	0.004 (3)	−0.029 (3)
C5	0.042 (3)	0.044 (3)	0.035 (3)	−0.017 (2)	0.000 (2)	−0.008 (2)
C6	0.046 (3)	0.056 (3)	0.056 (3)	−0.019 (3)	0.001 (3)	−0.015 (3)
C7	0.064 (4)	0.056 (3)	0.061 (4)	−0.024 (3)	0.012 (3)	−0.025 (3)
C8	0.077 (4)	0.074 (4)	0.062 (4)	−0.045 (3)	0.002 (3)	−0.025 (3)
C9	0.047 (3)	0.078 (4)	0.071 (4)	−0.029 (3)	−0.007 (3)	−0.014 (3)
C10	0.045 (3)	0.050 (3)	0.060 (4)	−0.014 (2)	−0.011 (3)	−0.006 (3)
C11	0.048 (3)	0.041 (3)	0.035 (3)	−0.007 (2)	−0.012 (2)	−0.014 (2)
C12	0.043 (3)	0.047 (3)	0.039 (3)	−0.018 (2)	−0.004 (2)	−0.011 (2)
C13	0.057 (3)	0.053 (3)	0.048 (3)	−0.009 (2)	−0.019 (3)	−0.009 (3)
C14	0.072 (4)	0.038 (3)	0.064 (4)	−0.010 (3)	−0.017 (3)	−0.004 (3)
C15	0.064 (3)	0.057 (3)	0.067 (4)	−0.026 (3)	0.010 (3)	−0.028 (3)
C16	0.072 (4)	0.072 (4)	0.053 (4)	−0.036 (3)	0.001 (3)	−0.033 (3)
C17	0.057 (3)	0.057 (3)	0.039 (3)	−0.021 (2)	−0.005 (2)	−0.013 (2)
C18	0.048 (3)	0.037 (2)	0.041 (3)	−0.018 (2)	−0.002 (2)	−0.013 (2)
C19	0.054 (3)	0.062 (3)	0.045 (3)	−0.022 (3)	−0.007 (3)	−0.024 (3)
C20	0.054 (3)	0.058 (3)	0.038 (3)	−0.018 (2)	−0.002 (2)	−0.018 (2)
C21	0.049 (3)	0.036 (2)	0.039 (3)	−0.010 (2)	−0.006 (2)	−0.008 (2)
C22	0.049 (3)	0.051 (3)	0.039 (3)	−0.020 (2)	−0.007 (2)	−0.013 (2)
C23	0.055 (3)	0.056 (3)	0.033 (3)	−0.018 (2)	−0.008 (2)	−0.013 (2)
C24	0.051 (3)	0.045 (3)	0.039 (3)	−0.012 (2)	−0.005 (2)	−0.009 (2)
C25	0.065 (4)	0.077 (4)	0.047 (4)	−0.016 (3)	0.001 (3)	−0.018 (3)
C26	0.113 (6)	0.106 (5)	0.127 (7)	−0.073 (5)	0.034 (5)	−0.052 (5)

Geometric parameters (Å, º) top

N1—C1	1.371 (5)	C12—C17	1.374 (6)
N1—N2	1.401 (5)	C12—C13	1.383 (6)
N1—C5	1.424 (5)	C13—C14	1.381 (7)
N2—C3	1.298 (5)	C13—H13	0.9300
N3—C11	1.321 (6)	C14—C15	1.352 (8)
N3—C18	1.421 (5)	C14—H14	0.9300
N3—H3	0.8600	C15—C16	1.387 (7)
N4—C24	1.263 (6)	C15—H15	0.9300
N4—O2	1.412 (5)	C16—C17	1.348 (6)
O1—C1	1.239 (5)	C16—H16	0.9300
O2—C26	1.423 (7)	C17—H17	0.9300
C1—C2	1.436 (6)	C18—C19	1.361 (6)
C2—C11	1.403 (6)	C18—C23	1.390 (6)
C2—C3	1.435 (6)	C19—C20	1.379 (6)
C3—C4	1.479 (7)	C19—H19	0.9300
C4—H4A	0.9600	C20—C21	1.378 (6)
C4—H4B	0.9600	C20—H20	0.9300
C4—H4C	0.9600	C21—C22	1.383 (6)
C5—C10	1.368 (6)	C21—C24	1.492 (6)
C5—C6	1.379 (6)	C22—C23	1.371 (6)
C6—C7	1.360 (6)	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.356 (7)	C24—C25	1.467 (7)
C7—H7	0.9300	C25—H25A	0.9600
C8—C9	1.378 (8)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C10	1.371 (7)	C26—H26A	0.9600
C9—H9	0.9300	C26—H26B	0.9600
C10—H10	0.9300	C26—H26C	0.9600
C11—C12	1.470 (6)

C1—N1—N2	112.5 (3)	C14—C13—C12	119.4 (5)
C1—N1—C5	127.5 (4)	C14—C13—H13	120.3
N2—N1—C5	119.3 (4)	C12—C13—H13	120.3
C3—N2—N1	106.5 (4)	C15—C14—C13	121.3 (5)
C11—N3—C18	129.1 (4)	C15—C14—H14	119.4
C11—N3—H3	115.4	C13—C14—H14	119.4
C18—N3—H3	115.4	C14—C15—C16	118.7 (5)
C24—N4—O2	111.5 (4)	C14—C15—H15	120.6
N4—O2—C26	109.4 (5)	C16—C15—H15	120.6
O1—C1—N1	126.3 (4)	C17—C16—C15	120.8 (5)
O1—C1—C2	129.8 (4)	C17—C16—H16	119.6
N1—C1—C2	103.8 (4)	C15—C16—H16	119.6
C11—C2—C3	131.8 (4)	C16—C17—C12	120.8 (5)
C11—C2—C1	121.9 (4)	C16—C17—H17	119.6
C3—C2—C1	106.1 (4)	C12—C17—H17	119.6
N2—C3—C2	111.0 (4)	C19—C18—C23	119.5 (4)
N2—C3—C4	119.2 (4)	C19—C18—N3	119.2 (4)
C2—C3—C4	129.8 (4)	C23—C18—N3	121.2 (4)
C3—C4—H4A	109.5	C18—C19—C20	121.1 (4)
C3—C4—H4B	109.5	C18—C19—H19	119.5
H4A—C4—H4B	109.5	C20—C19—H19	119.5
C3—C4—H4C	109.5	C21—C20—C19	120.3 (5)
H4A—C4—H4C	109.5	C21—C20—H20	119.9
H4B—C4—H4C	109.5	C19—C20—H20	119.9
C10—C5—C6	120.2 (4)	C20—C21—C22	118.2 (4)
C10—C5—N1	120.6 (4)	C20—C21—C24	120.6 (4)
C6—C5—N1	119.1 (4)	C22—C21—C24	121.1 (4)
C7—C6—C5	119.7 (5)	C23—C22—C21	121.8 (4)
C7—C6—H6	120.2	C23—C22—H22	119.1
C5—C6—H6	120.2	C21—C22—H22	119.1
C8—C7—C6	120.8 (5)	C22—C23—C18	119.1 (4)
C8—C7—H7	119.6	C22—C23—H23	120.4
C6—C7—H7	119.6	C18—C23—H23	120.4
C7—C8—C9	119.6 (5)	N4—C24—C25	124.5 (4)
C7—C8—H8	120.2	N4—C24—C21	114.6 (4)
C9—C8—H8	120.2	C25—C24—C21	120.7 (4)
C10—C9—C8	120.3 (5)	C24—C25—H25A	109.5
C10—C9—H9	119.9	C24—C25—H25B	109.5
C8—C9—H9	119.9	H25A—C25—H25B	109.5
C5—C10—C9	119.4 (5)	C24—C25—H25C	109.5
C5—C10—H10	120.3	H25A—C25—H25C	109.5
C9—C10—H10	120.3	H25B—C25—H25C	109.5
N3—C11—C2	117.6 (4)	O2—C26—H26A	109.5
N3—C11—C12	119.0 (4)	O2—C26—H26B	109.5
C2—C11—C12	123.3 (4)	H26A—C26—H26B	109.5
C17—C12—C13	119.0 (4)	O2—C26—H26C	109.5
C17—C12—C11	122.1 (4)	H26A—C26—H26C	109.5
C13—C12—C11	118.9 (4)	H26B—C26—H26C	109.5

C1—N1—N2—C3	3.3 (5)	C3—C2—C11—C12	−5.7 (7)
C5—N1—N2—C3	174.7 (4)	C1—C2—C11—C12	−179.8 (4)
C24—N4—O2—C26	−169.8 (5)	N3—C11—C12—C17	110.5 (5)
N2—N1—C1—O1	174.2 (4)	C2—C11—C12—C17	−73.3 (6)
C5—N1—C1—O1	3.7 (7)	N3—C11—C12—C13	−69.0 (6)
N2—N1—C1—C2	−3.2 (5)	C2—C11—C12—C13	107.2 (5)
C5—N1—C1—C2	−173.8 (4)	C17—C12—C13—C14	−0.6 (7)
O1—C1—C2—C11	0.1 (7)	C11—C12—C13—C14	179.0 (4)
N1—C1—C2—C11	177.4 (4)	C12—C13—C14—C15	−1.2 (8)
O1—C1—C2—C3	−175.3 (5)	C13—C14—C15—C16	1.4 (8)
N1—C1—C2—C3	1.9 (5)	C14—C15—C16—C17	0.0 (8)
N1—N2—C3—C2	−1.8 (5)	C15—C16—C17—C12	−1.8 (8)
N1—N2—C3—C4	−179.4 (4)	C13—C12—C17—C16	2.0 (7)
C11—C2—C3—N2	−174.9 (4)	C11—C12—C17—C16	−177.5 (4)
C1—C2—C3—N2	−0.1 (5)	C11—N3—C18—C19	132.8 (5)
C11—C2—C3—C4	2.3 (8)	C11—N3—C18—C23	−51.4 (7)
C1—C2—C3—C4	177.1 (5)	C23—C18—C19—C20	0.5 (7)
C1—N1—C5—C10	133.8 (5)	N3—C18—C19—C20	176.3 (4)
N2—N1—C5—C10	−36.2 (6)	C18—C19—C20—C21	1.1 (7)
C1—N1—C5—C6	−44.1 (7)	C19—C20—C21—C22	−1.1 (7)
N2—N1—C5—C6	145.9 (4)	C19—C20—C21—C24	177.4 (4)
C10—C5—C6—C7	−1.6 (8)	C20—C21—C22—C23	−0.5 (7)
N1—C5—C6—C7	176.2 (5)	C24—C21—C22—C23	−179.0 (4)
C5—C6—C7—C8	1.3 (8)	C21—C22—C23—C18	2.0 (7)
C6—C7—C8—C9	−0.1 (9)	C19—C18—C23—C22	−2.0 (7)
C7—C8—C9—C10	−0.7 (9)	N3—C18—C23—C22	−177.8 (4)
C6—C5—C10—C9	0.8 (8)	O2—N4—C24—C25	0.9 (7)
N1—C5—C10—C9	−177.0 (5)	O2—N4—C24—C21	176.2 (4)
C8—C9—C10—C5	0.4 (9)	C20—C21—C24—N4	−146.8 (5)
C18—N3—C11—C2	178.2 (4)	C22—C21—C24—N4	31.6 (7)
C18—N3—C11—C12	−5.4 (7)	C20—C21—C24—C25	28.7 (7)
C3—C2—C11—N3	170.6 (5)	C22—C21—C24—C25	−152.9 (5)
C1—C2—C11—N3	−3.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.95	2.683 (4)	142
C26—H26C···N4ⁱ	0.96	2.72	3.643 (9)	163
C9—H9···O1ⁱⁱ	0.93	2.67	3.398 (6)	135

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₄O₂
M_r	424.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3550 (6), 11.1609 (13), 14.9700 (12)
α, β, γ (°)	68.536 (1), 76.654 (2), 76.182 (2)
V (Å³)	1096.46 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.49 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5654, 3781, 1861
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.246, 1.03
No. of reflections	3781
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N3—H3···O1	0.86	1.95	2.683 (4)	142.3
C26—H26C···N4ⁱ	0.96	2.72	3.643 (9)	162.8
C9—H9···O1ⁱⁱ	0.93	2.67	3.398 (6)	135.3

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

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (0904–11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

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
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573. CrossRef CAS Web of Science Google Scholar
Bomfim, J. A. S., Wardell, J. L., Low, J. N., Skakle, J. M. S. & Glidewell, C. (2005). Acta Cryst. C61, o53–o56. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Dong, W.-K., He, X.-N., Sun, Y.-X., Xu, L. & Guan, Y.-H. (2008). Acta Cryst. E64, o1917. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lahiri, S., Wu, X. L., Yang, W. F., Xu, Y. B. & Yuan, S. G. (2003). J. Radioanal. Nucl. Chem. 257, 431–432. Web of Science CrossRef CAS Google Scholar
Rafiq, M., Hanif, M., Qadeer, G., Vuoti, S. & Autio, J. (2008). Acta Cryst. E64, o2173. Web of Science CSD CrossRef IUCr Journals 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wang, J.-S., Jiang, Y.-L., Dong, W.-K., Xu, L. & Kong, A.-P. (2008). Acta Cryst. E64, o1794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, L., Dong, W.-K., Wu, J.-C., Sun, Y.-X. & Xu, L. (2009). Acta Cryst. E65, o2462. Web of Science CSD CrossRef IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3122-o3123

doi:10.1107/S1600536809048326

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-({4-[1-(Meth­oxy­imino)eth­yl]anilino}(phen­yl)methyl­ene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-({4-[1-(Methoxyimino)ethyl]anilino}(phenyl)methylene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one