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

Liu, S.-X.; Tian, X.; Zhen, X.-L.; Li, Z.-C.; Han, J.-R.

doi:10.1107/S1600536808035046

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2245

doi:10.1107/S1600536808035046

Open

access

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

Shou-Xin Liu,^a ^* Xia Tian,^b Xiao-Li Zhen,^b Zhen-Chao Li ^b and Jian-Rong Han ^b ‡

^aCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: liu_shouxin@163.com

(Received 27 October 2008; accepted 28 October 2008; online 31 October 2008)

In the title compound, C₂₅H₂₂N₄O₄, the central benzene ring, makes dihedral angles of 74.35 (6), 17.01 (8) and 62.19 (7)°, respectively, with the nitrobenzyl ring, the pyrazolone ring and the terminal phenyl ring. Intermolecular C—H⋯O hydrogen bonds help to consolidate the crystal packing.

Related literature

For the potential applications of Schiff bases, see: Jones et al. (1979 ); Larson & Pecoraro (1991 ); Santos et al. (2001 ). For a related structure, see: Han & Zhen (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₂₂N₄O₄
M_r = 442.47
Triclinic, $[P \overline 1]$
a = 8.003 (2) Å
b = 9.798 (3) Å
c = 14.425 (5) Å
α = 90.844 (5)°
β = 92.310 (6)°
γ = 101.202 (6)°
V = 1108.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.991
5780 measured reflections
3898 independent reflections
2302 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.01
3898 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O4ⁱ	0.97	2.50	3.293 (3)	139
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 1999 ); 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/S1600536808035046/hb2829sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035046/hb2829Isup2.hkl

checkCIF report

Comment top

There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of the compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of them, such as (E)-(4)-(3-ethoxy-4-hydroxybenzylideneamino)- 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Han & Zhen, 2005) have been reported. In present study we report the syntheses and molecular structure of the title compound, (I), (Fig. 1).

The bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The pyrazolone ring (C15—C17/N2—N4/O4) is close to planar, with an r.m.s. deviation for the fitted atoms of 0.0441 Å. It makes a dihedral angle of 49.38 (8)° with the attached phenyl ring (C20—C25). The central benzene ring (C8—C14/O3) is also planar, with an r.m.s. deviation for the fitted atoms of 0.0079 Å, and it makes dihedral angles of 74.35 (6)°, 17.01 (8)° and 62.19 (7)° with the nitrobenzyl ring (C1—C7), the pyrazolone ring (C15—C17/N2—N4/O4) and the terminal phenyl ring (C20—C25), respectively.

Packing is stabilized by weak, non-classical intermolecular C7—H7B···O4ⁱ (symmetry code (i): 2 - x, 1 - y, -z) hydrogen bonds that form inversion related dimers, (Fig. 2, Table 1).

Related literature top

For general background, see: Allen et al. (1987); Han & Zhen (2005) Jones et al. (1979); Larson & Pecoraro, (1991); Santos et al. (2001).

Experimental top

An anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) was added to an anhydrous ethanol solution (100 ml) of 3-(4-nitrobenzyloxy)benzaldehyde (2.57 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile and then dried in a vacuum to give the pure compound in 81% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Computing details top

Data collection: SMART (Bruker, 1999); 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) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines.

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

Crystal data top

C₂₅H₂₂N₄O₄	Z = 2
M_r = 442.47	F(000) = 464
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.003 (2) Å	Cell parameters from 2119 reflections
b = 9.798 (3) Å	θ = 2.4–23.9°
c = 14.425 (5) Å	µ = 0.09 mm⁻¹
α = 90.844 (5)°	T = 294 K
β = 92.310 (6)°	Block, yellow
γ = 101.202 (6)°	0.20 × 0.18 × 0.10 mm
V = 1108.4 (6) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3898 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→9
T_min = 0.956, T_max = 0.991	k = −11→11
5780 measured reflections	l = −16→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0501P)² + 0.1798P] where P = (F_o² + 2F_c²)/3
3898 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₅H₂₂N₄O₄	γ = 101.202 (6)°
M_r = 442.47	V = 1108.4 (6) Å³
Triclinic, P1	Z = 2
a = 8.003 (2) Å	Mo Kα radiation
b = 9.798 (3) Å	µ = 0.09 mm⁻¹
c = 14.425 (5) Å	T = 294 K
α = 90.844 (5)°	0.20 × 0.18 × 0.10 mm
β = 92.310 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3898 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2302 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.991	R_int = 0.026
5780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
3898 reflections	Δρ_min = −0.16 e Å⁻³
300 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 > 2σ(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	1.8078 (5)	0.2593 (4)	0.4869 (2)	0.0967 (10)
N2	0.7686 (2)	0.2222 (2)	0.00080 (12)	0.0422 (5)
N3	0.5534 (2)	−0.05908 (19)	−0.14560 (13)	0.0457 (5)
N4	0.4987 (2)	0.05116 (19)	−0.19115 (13)	0.0456 (5)
O1	1.9568 (4)	0.3106 (3)	0.4734 (2)	0.1346 (12)
O2	1.7631 (4)	0.1619 (4)	0.5360 (2)	0.1486 (14)
O3	1.2066 (2)	0.43844 (16)	0.24686 (11)	0.0527 (5)
O4	0.5147 (2)	0.28509 (17)	−0.15735 (12)	0.0599 (5)
C1	1.3860 (3)	0.3378 (3)	0.42021 (17)	0.0575 (7)
H1	1.2725	0.3070	0.4338	0.069*
C2	1.5095 (4)	0.2734 (3)	0.45952 (17)	0.0656 (8)
H2	1.4805	0.1987	0.4986	0.079*
C3	1.6757 (4)	0.3223 (3)	0.43939 (19)	0.0625 (8)
C4	1.7205 (4)	0.4273 (3)	0.3794 (2)	0.0727 (9)
H4	1.8340	0.4570	0.3654	0.087*
C5	1.5966 (4)	0.4887 (3)	0.3400 (2)	0.0634 (8)
H5	1.6262	0.5597	0.2981	0.076*
C6	1.4285 (3)	0.4471 (2)	0.36121 (16)	0.0458 (6)
C7	1.2964 (3)	0.5206 (3)	0.32183 (17)	0.0554 (7)
H7A	1.2181	0.5341	0.3692	0.066*
H7B	1.3500	0.6111	0.3001	0.066*
C8	1.0789 (3)	0.4895 (2)	0.20062 (15)	0.0409 (6)
C9	0.9887 (3)	0.4033 (2)	0.13208 (15)	0.0402 (6)
H9	1.0185	0.3181	0.1191	0.048*
C10	0.8547 (3)	0.4415 (2)	0.08225 (15)	0.0390 (6)
C11	0.8139 (3)	0.5693 (2)	0.10135 (17)	0.0510 (6)
H11	0.7245	0.5969	0.0682	0.061*
C12	0.9050 (3)	0.6558 (3)	0.16911 (17)	0.0553 (7)
H12	0.8768	0.7419	0.1811	0.066*
C13	1.0377 (3)	0.6174 (2)	0.21982 (16)	0.0480 (6)
H13	1.0982	0.6764	0.2660	0.058*
C14	0.7563 (3)	0.3497 (2)	0.01004 (15)	0.0439 (6)
H14	0.6827	0.3853	−0.0303	0.053*
C15	0.6729 (3)	0.1381 (2)	−0.06885 (15)	0.0394 (6)
C16	0.6681 (3)	−0.0010 (2)	−0.07688 (16)	0.0430 (6)
C17	0.5600 (3)	0.1751 (3)	−0.14076 (16)	0.0441 (6)
C18	0.7646 (3)	−0.0883 (3)	−0.02119 (19)	0.0609 (7)
H18A	0.6885	−0.1712	−0.0035	0.091*
H18B	0.8151	−0.0370	0.0335	0.091*
H18C	0.8526	−0.1131	−0.0575	0.091*
C19	0.5755 (4)	−0.1761 (3)	−0.2039 (2)	0.0815 (10)
H19A	0.6626	−0.1452	−0.2470	0.122*
H19B	0.4702	−0.2136	−0.2374	0.122*
H19C	0.6085	−0.2467	−0.1657	0.122*
C20	0.3426 (3)	0.0258 (2)	−0.24550 (15)	0.0429 (6)
C21	0.2107 (3)	−0.0796 (3)	−0.22521 (17)	0.0546 (7)
H21	0.2218	−0.1376	−0.1758	0.066*
C22	0.0611 (3)	−0.0984 (3)	−0.2790 (2)	0.0678 (8)
H22	−0.0270	−0.1724	−0.2673	0.081*
C23	0.0401 (4)	−0.0105 (3)	−0.34928 (19)	0.0680 (8)
H23	−0.0626	−0.0221	−0.3838	0.082*
C24	0.1725 (4)	0.0950 (3)	−0.36802 (19)	0.0677 (8)
H24	0.1593	0.1557	−0.4155	0.081*
C25	0.3243 (3)	0.1123 (3)	−0.31772 (17)	0.0590 (7)
H25	0.4148	0.1824	−0.3324	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.086 (2)	0.139 (3)	0.079 (2)	0.064 (2)	−0.0193 (19)	−0.031 (2)
N2	0.0413 (11)	0.0414 (12)	0.0430 (12)	0.0069 (9)	−0.0026 (9)	0.0009 (9)
N3	0.0454 (12)	0.0396 (12)	0.0529 (12)	0.0122 (9)	−0.0050 (10)	−0.0050 (10)
N4	0.0458 (12)	0.0429 (12)	0.0461 (12)	0.0060 (9)	−0.0088 (9)	−0.0012 (10)
O1	0.0696 (18)	0.178 (3)	0.167 (3)	0.0610 (19)	−0.0341 (18)	−0.045 (2)
O2	0.151 (3)	0.210 (4)	0.117 (3)	0.116 (3)	−0.005 (2)	0.049 (2)
O3	0.0569 (10)	0.0463 (10)	0.0548 (11)	0.0148 (8)	−0.0200 (8)	−0.0083 (8)
O4	0.0688 (12)	0.0429 (11)	0.0664 (12)	0.0114 (9)	−0.0219 (9)	0.0046 (9)
C1	0.0452 (15)	0.0752 (19)	0.0525 (16)	0.0124 (14)	0.0027 (13)	0.0078 (14)
C2	0.073 (2)	0.090 (2)	0.0424 (16)	0.0360 (17)	0.0040 (14)	0.0140 (14)
C3	0.0520 (18)	0.094 (2)	0.0489 (17)	0.0370 (17)	−0.0127 (14)	−0.0179 (16)
C4	0.0469 (18)	0.086 (2)	0.083 (2)	0.0065 (16)	0.0052 (16)	−0.0171 (19)
C5	0.0579 (19)	0.0587 (18)	0.071 (2)	0.0040 (15)	0.0047 (15)	−0.0012 (14)
C6	0.0453 (15)	0.0501 (15)	0.0398 (14)	0.0061 (12)	−0.0059 (11)	−0.0075 (12)
C7	0.0619 (17)	0.0515 (16)	0.0502 (16)	0.0097 (13)	−0.0169 (13)	−0.0061 (12)
C8	0.0443 (14)	0.0389 (14)	0.0392 (13)	0.0080 (11)	−0.0015 (11)	0.0033 (11)
C9	0.0441 (14)	0.0319 (13)	0.0444 (14)	0.0074 (11)	0.0001 (11)	−0.0016 (11)
C10	0.0412 (14)	0.0371 (14)	0.0385 (13)	0.0066 (11)	0.0011 (11)	0.0039 (11)
C11	0.0568 (16)	0.0473 (15)	0.0524 (16)	0.0207 (13)	−0.0074 (12)	0.0027 (12)
C12	0.0704 (18)	0.0422 (15)	0.0566 (17)	0.0211 (14)	−0.0041 (14)	−0.0063 (13)
C13	0.0572 (16)	0.0411 (15)	0.0457 (15)	0.0117 (12)	−0.0049 (12)	−0.0067 (11)
C14	0.0427 (14)	0.0462 (16)	0.0429 (14)	0.0099 (11)	−0.0038 (11)	0.0055 (11)
C15	0.0392 (13)	0.0386 (14)	0.0390 (13)	0.0055 (11)	−0.0042 (11)	0.0009 (11)
C16	0.0377 (13)	0.0432 (15)	0.0481 (15)	0.0091 (11)	−0.0009 (11)	−0.0016 (11)
C17	0.0427 (14)	0.0426 (15)	0.0451 (15)	0.0041 (12)	−0.0003 (11)	0.0031 (12)
C18	0.0627 (17)	0.0536 (16)	0.0697 (19)	0.0229 (14)	−0.0131 (14)	−0.0031 (14)
C19	0.081 (2)	0.075 (2)	0.094 (2)	0.0380 (17)	−0.0233 (18)	−0.0422 (18)
C20	0.0447 (14)	0.0440 (14)	0.0387 (14)	0.0075 (12)	−0.0061 (11)	−0.0029 (11)
C21	0.0507 (16)	0.0564 (16)	0.0528 (16)	0.0015 (13)	−0.0078 (13)	0.0144 (13)
C22	0.0507 (17)	0.0715 (19)	0.075 (2)	−0.0033 (14)	−0.0114 (15)	0.0185 (16)
C23	0.0587 (18)	0.074 (2)	0.0666 (19)	0.0077 (16)	−0.0233 (14)	0.0060 (16)
C24	0.082 (2)	0.0652 (19)	0.0503 (17)	0.0049 (17)	−0.0183 (15)	0.0127 (14)
C25	0.0632 (18)	0.0593 (17)	0.0465 (16)	−0.0056 (14)	−0.0095 (13)	0.0063 (13)

Geometric parameters (Å, º) top

N1—O2	1.204 (4)	C9—H9	0.9300
N1—O1	1.226 (4)	C10—C11	1.380 (3)
N1—C3	1.474 (4)	C10—C14	1.464 (3)
N2—C14	1.278 (3)	C11—C12	1.372 (3)
N2—C15	1.394 (3)	C11—H11	0.9300
N3—C16	1.362 (3)	C12—C13	1.380 (3)
N3—N4	1.404 (3)	C12—H12	0.9300
N3—C19	1.454 (3)	C13—H13	0.9300
N4—C17	1.399 (3)	C14—H14	0.9300
N4—C20	1.425 (3)	C15—C16	1.360 (3)
O3—C8	1.376 (3)	C15—C17	1.444 (3)
O3—C7	1.422 (3)	C16—C18	1.483 (3)
O4—C17	1.225 (3)	C18—H18A	0.9600
C1—C6	1.377 (3)	C18—H18B	0.9600
C1—C2	1.380 (3)	C18—H18C	0.9600
C1—H1	0.9300	C19—H19A	0.9600
C2—C3	1.368 (4)	C19—H19B	0.9600
C2—H2	0.9300	C19—H19C	0.9600
C3—C4	1.358 (4)	C20—C21	1.370 (3)
C4—C5	1.366 (4)	C20—C25	1.373 (3)
C4—H4	0.9300	C21—C22	1.380 (3)
C5—C6	1.376 (3)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.366 (4)
C6—C7	1.489 (3)	C22—H22	0.9300
C7—H7A	0.9700	C23—C24	1.367 (4)
C7—H7B	0.9700	C23—H23	0.9300
C8—C9	1.375 (3)	C24—C25	1.370 (4)
C8—C13	1.383 (3)	C24—H24	0.9300
C9—C10	1.382 (3)	C25—H25	0.9300

O2—N1—O1	124.4 (4)	C11—C12—H12	119.4
O2—N1—C3	118.4 (4)	C13—C12—H12	119.4
O1—N1—C3	117.2 (4)	C12—C13—C8	118.6 (2)
C14—N2—C15	120.26 (19)	C12—C13—H13	120.7
C16—N3—N4	106.75 (17)	C8—C13—H13	120.7
C16—N3—C19	123.4 (2)	N2—C14—C10	122.0 (2)
N4—N3—C19	116.3 (2)	N2—C14—H14	119.0
C17—N4—N3	109.20 (18)	C10—C14—H14	119.0
C17—N4—C20	123.36 (19)	C16—C15—N2	123.0 (2)
N3—N4—C20	119.91 (18)	C16—C15—C17	107.85 (19)
C8—O3—C7	117.38 (18)	N2—C15—C17	129.1 (2)
C6—C1—C2	121.0 (2)	C15—C16—N3	110.6 (2)
C6—C1—H1	119.5	C15—C16—C18	128.7 (2)
C2—C1—H1	119.5	N3—C16—C18	120.7 (2)
C3—C2—C1	118.2 (3)	O4—C17—N4	123.6 (2)
C3—C2—H2	120.9	O4—C17—C15	131.6 (2)
C1—C2—H2	120.9	N4—C17—C15	104.81 (19)
C4—C3—C2	122.0 (3)	C16—C18—H18A	109.5
C4—C3—N1	120.2 (3)	C16—C18—H18B	109.5
C2—C3—N1	117.8 (3)	H18A—C18—H18B	109.5
C3—C4—C5	119.1 (3)	C16—C18—H18C	109.5
C3—C4—H4	120.4	H18A—C18—H18C	109.5
C5—C4—H4	120.4	H18B—C18—H18C	109.5
C4—C5—C6	121.0 (3)	N3—C19—H19A	109.5
C4—C5—H5	119.5	N3—C19—H19B	109.5
C6—C5—H5	119.5	H19A—C19—H19B	109.5
C5—C6—C1	118.6 (2)	N3—C19—H19C	109.5
C5—C6—C7	120.3 (2)	H19A—C19—H19C	109.5
C1—C6—C7	121.0 (2)	H19B—C19—H19C	109.5
O3—C7—C6	108.51 (19)	C21—C20—C25	120.1 (2)
O3—C7—H7A	110.0	C21—C20—N4	121.3 (2)
C6—C7—H7A	110.0	C25—C20—N4	118.6 (2)
O3—C7—H7B	110.0	C20—C21—C22	119.1 (2)
C6—C7—H7B	110.0	C20—C21—H21	120.5
H7A—C7—H7B	108.4	C22—C21—H21	120.5
C9—C8—O3	115.52 (19)	C23—C22—C21	121.2 (3)
C9—C8—C13	120.2 (2)	C23—C22—H22	119.4
O3—C8—C13	124.3 (2)	C21—C22—H22	119.4
C8—C9—C10	121.0 (2)	C22—C23—C24	118.9 (3)
C8—C9—H9	119.5	C22—C23—H23	120.5
C10—C9—H9	119.5	C24—C23—H23	120.5
C11—C10—C9	118.8 (2)	C23—C24—C25	120.8 (3)
C11—C10—C14	119.8 (2)	C23—C24—H24	119.6
C9—C10—C14	121.4 (2)	C25—C24—H24	119.6
C12—C11—C10	120.2 (2)	C24—C25—C20	119.8 (2)
C12—C11—H11	119.9	C24—C25—H25	120.1
C10—C11—H11	119.9	C20—C25—H25	120.1
C11—C12—C13	121.2 (2)

C16—N3—N4—C17	−9.3 (2)	C15—N2—C14—C10	−180.0 (2)
C19—N3—N4—C17	−151.5 (2)	C11—C10—C14—N2	−167.5 (2)
C16—N3—N4—C20	−160.00 (19)	C9—C10—C14—N2	12.7 (3)
C19—N3—N4—C20	57.8 (3)	C14—N2—C15—C16	−173.7 (2)
C6—C1—C2—C3	1.0 (4)	C14—N2—C15—C17	3.7 (3)
C1—C2—C3—C4	−2.9 (4)	N2—C15—C16—N3	174.59 (19)
C1—C2—C3—N1	175.8 (2)	C17—C15—C16—N3	−3.3 (3)
O2—N1—C3—C4	−176.4 (3)	N2—C15—C16—C18	−3.9 (4)
O1—N1—C3—C4	3.8 (4)	C17—C15—C16—C18	178.2 (2)
O2—N1—C3—C2	4.9 (5)	N4—N3—C16—C15	7.7 (3)
O1—N1—C3—C2	−174.9 (3)	C19—N3—C16—C15	146.6 (2)
C2—C3—C4—C5	1.9 (4)	N4—N3—C16—C18	−173.6 (2)
N1—C3—C4—C5	−176.7 (3)	C19—N3—C16—C18	−34.8 (4)
C3—C4—C5—C6	1.0 (4)	N3—N4—C17—O4	−170.3 (2)
C4—C5—C6—C1	−2.8 (4)	C20—N4—C17—O4	−20.9 (4)
C4—C5—C6—C7	176.5 (2)	N3—N4—C17—C15	7.2 (2)
C2—C1—C6—C5	1.8 (4)	C20—N4—C17—C15	156.7 (2)
C2—C1—C6—C7	−177.4 (2)	C16—C15—C17—O4	174.8 (3)
C8—O3—C7—C6	−179.61 (19)	N2—C15—C17—O4	−2.9 (4)
C5—C6—C7—O3	101.9 (3)	C16—C15—C17—N4	−2.5 (2)
C1—C6—C7—O3	−78.9 (3)	N2—C15—C17—N4	179.8 (2)
C7—O3—C8—C9	−176.4 (2)	C17—N4—C20—C21	−117.6 (3)
C7—O3—C8—C13	2.9 (3)	N3—N4—C20—C21	28.8 (3)
O3—C8—C9—C10	178.4 (2)	C17—N4—C20—C25	60.5 (3)
C13—C8—C9—C10	−0.9 (3)	N3—N4—C20—C25	−153.1 (2)
C8—C9—C10—C11	1.1 (3)	C25—C20—C21—C22	0.9 (4)
C8—C9—C10—C14	−179.1 (2)	N4—C20—C21—C22	179.0 (2)
C9—C10—C11—C12	−0.4 (4)	C20—C21—C22—C23	−2.8 (4)
C14—C10—C11—C12	179.8 (2)	C21—C22—C23—C24	2.2 (5)
C10—C11—C12—C13	−0.4 (4)	C22—C23—C24—C25	0.3 (5)
C11—C12—C13—C8	0.5 (4)	C23—C24—C25—C20	−2.2 (4)
C9—C8—C13—C12	0.2 (3)	C21—C20—C25—C24	1.6 (4)
O3—C8—C13—C12	−179.1 (2)	N4—C20—C25—C24	−176.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O4ⁱ	0.97	2.50	3.293 (3)	139

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₄O₄
M_r	442.47
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.003 (2), 9.798 (3), 14.425 (5)
α, β, γ (°)	90.844 (5), 92.310 (6), 101.202 (6)
V (Å³)	1108.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	5780, 3898, 2302
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.01
No. of reflections	3898
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Bruker, 1999), 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
C7—H7B···O4ⁱ	0.97	2.50	3.293 (3)	139

Symmetry code: (i) −x+2, −y+1, −z.

Footnotes

‡Additional contact author, e-mail: han_jianrong@163.com.

Acknowledgements

The project was supported by the Foundation of the Education Department of Hebei Province (grant No. 606022).

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
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o3815–o3816. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 17, 139–179. CrossRef Web of Science Google Scholar
Larson, E. J. & Pecoraro, V. L. (1991). J. Am. Chem. Soc. 113, 3810–3818. CSD CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef 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

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 64| Part 11| November 2008| Page o2245

doi:10.1107/S1600536808035046

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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