(E)-1,5-Dimethyl-4-[3-(4-nitro-benz-yloxy)benzyl-ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one.

In the title compound, C(25)H(22)N(4)O(4), the central benzene ring, makes dihedral angles of 74.35 (6), 17.01 (8) and 62.19 (7)°, respectively, with the nitro-benzyl ring, the pyrazolone ring and the terminal phenyl ring. Inter-molecular 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 = 442.47

Triclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.01

3898 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035046/hb2829sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H22N4O4	Z = 2
Mr = 442.47	F(000) = 464
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0501P)2 + 0.1798P] where P = (Fo2 + 2Fc2)/3
3898 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .