4-({4-[1-(Methoxy-imino)eth-yl]anilino}(phen-yl)methyl-ene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one.

In the title compound, C(26)H(24)N(4)O(2), 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 intra-molecular N-H⋯O hydrogen bond forms a six-membered ring with an S(6) motif. In the crystal structure, a weak inter-molecular C-H⋯N inter-action with graph-set motif R(2) (2)(8) and C-H⋯O hydrogen bonds link each mol-ecule to three others, forming an infinite two-dimensional supra-molecular 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 = 424.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.246

S = 1.03

3781 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048326/fl2280sup1.cif

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

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

C26H24N4O2	Z = 2
Mr = 424.49	F(000) = 448
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1078P)2 + 0.3814P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3781 reflections	Δρmax = 0.24 e Å−3
290 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .