4-[(Z)-(2-Fur-yl)(2-naphthyl-amino)methyl-ene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

The title compound, C(25)H(19)N(3)O(2), crystallizes as discrete mol-ecules which are well ordered through one intra-molecular N-H⋯O hydrogen bond. Structural analysis indicates that the mol-ecules exist as the amine-one form.

Related literature

For 4-heterocyclic acyl­pyrazolones, see: Dong et al. (1983 ▶). For 4-heterocyclic acyl­pyrazolones derivatives as NMR shift-reagents, see: Mehrotra et al. (1978 ▶). For their pharmacological and physiological activity, see: Li et al. (2000 ▶). For related structures, see: Uzoukwu et al.(1993 ▶); Holzer et al. (1999 ▶); Peng et al. (2004 ▶); Chai et al. (2005 ▶); Lü et al. (2006 ▶); Arıcı et al. (1999 ▶). For the synthesis, see: Jensen (1959 ▶).

Experimental

Crystal data

C25H19N3O2

M = 393.43

Monoclinic,

a = 9.8484 (10) Å

b = 17.5071 (18) Å

c = 12.1549 (13) Å

β = 108.836 (2)°

V = 1983.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.44 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T min = 0.959, T max = 0.983

13952 measured reflections

4755 independent reflections

3166 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.05

4755 reflections

276 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025586/hg2530sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025586/hg2530Isup2.hkl

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

C25H19N3O2	F(000) = 824.0
Mr = 393.43	Dx = 1.317 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3130 reflections
a = 9.8484 (10) Å	θ = 2.6–28.0°
b = 17.5071 (18) Å	µ = 0.09 mm−1
c = 12.1549 (13) Å	T = 295 K
β = 108.836 (2)°	Block, yellow
V = 1983.5 (4) Å3	0.44 × 0.30 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4755 independent reflections
Radiation source: fine-focus sealed tube	3166 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	h = −12→12
Tmin = 0.959, Tmax = 0.983	k = −23→21
13952 measured reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.05P)2 + 0.2364P] where P = (Fo2 + 2Fc2)/3
4755 reflections	(Δ/σ)max = 0.001
276 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 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 > 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
O1	0.31096 (12)	0.99855 (6)	0.59990 (9)	0.0549 (3)
N2	0.45802 (13)	0.85606 (7)	0.46997 (10)	0.0432 (3)
N1	0.34379 (12)	0.90162 (7)	0.47756 (10)	0.0399 (3)
N3	0.55828 (15)	1.02258 (7)	0.77544 (11)	0.0465 (3)
O2	0.75042 (12)	0.85524 (6)	0.83717 (10)	0.0592 (3)
C1	0.20702 (15)	0.89273 (8)	0.39232 (12)	0.0390 (3)
C11	0.61359 (16)	0.96190 (8)	0.73800 (12)	0.0397 (3)
C7	0.38634 (16)	0.94942 (8)	0.57273 (12)	0.0406 (3)
C16	0.59012 (16)	1.05724 (9)	0.88701 (13)	0.0449 (4)
C9	0.56923 (16)	0.87256 (8)	0.56016 (12)	0.0409 (3)
C8	0.53422 (15)	0.92941 (8)	0.63218 (12)	0.0394 (3)
C12	0.75221 (16)	0.93050 (8)	0.80752 (12)	0.0418 (3)
C6	0.19138 (17)	0.84437 (9)	0.29868 (13)	0.0457 (4)
H6	0.2712	0.8203	0.2895	0.055*
C25	0.53169 (17)	1.13195 (9)	0.88745 (13)	0.0469 (4)
C17	0.65935 (18)	1.02042 (10)	0.98919 (14)	0.0535 (4)
H17	0.6968	0.9718	0.9881	0.064*
C2	0.08712 (17)	0.92954 (9)	0.40357 (14)	0.0490 (4)
H2	0.0965	0.9628	0.4653	0.059*
C4	−0.06237 (18)	0.86776 (10)	0.23023 (15)	0.0564 (4)
H4	−0.1525	0.8592	0.1763	0.068*
C10	0.71017 (17)	0.83648 (10)	0.57112 (15)	0.0563 (4)
H10A	0.7012	0.8060	0.5035	0.085*
H10B	0.7393	0.8047	0.6391	0.085*
H10C	0.7808	0.8756	0.5778	0.085*
C18	0.67368 (19)	1.05648 (12)	1.09619 (14)	0.0628 (5)
H18	0.7246	1.0322	1.1653	0.075*
C24	0.46253 (18)	1.17379 (10)	0.78515 (15)	0.0546 (4)
H24	0.4562	1.1530	0.7133	0.065*
C5	0.05709 (18)	0.83200 (10)	0.21910 (14)	0.0534 (4)
H5	0.0471	0.7990	0.1570	0.064*
C3	−0.04613 (18)	0.91643 (10)	0.32260 (15)	0.0564 (4)
H3	−0.1262	0.9409	0.3306	0.068*
C19	0.6143 (2)	1.12593 (12)	1.09975 (15)	0.0645 (5)
H19	0.6215	1.1477	1.1712	0.077*
C13	0.88543 (18)	0.95840 (10)	0.85144 (14)	0.0545 (4)
H13	0.9150	1.0081	0.8444	0.065*
C21	0.4782 (2)	1.23835 (12)	0.99697 (19)	0.0748 (6)
H21	0.4819	1.2605	1.0675	0.090*
C20	0.54195 (19)	1.16567 (10)	0.99658 (15)	0.0561 (4)
C15	0.8882 (2)	0.83722 (11)	0.90023 (15)	0.0651 (5)
H15	0.9184	0.7893	0.9315	0.078*
C14	0.97269 (19)	0.89690 (11)	0.91091 (16)	0.0624 (5)
H14	1.0709	0.8985	0.9500	0.075*
C23	0.4050 (2)	1.24393 (11)	0.78978 (18)	0.0689 (5)
H23	0.3609	1.2706	0.7214	0.083*
C22	0.4119 (3)	1.27615 (12)	0.8966 (2)	0.0804 (6)
H22	0.3708	1.3237	0.8988	0.096*
H3A	0.4738 (19)	1.0356 (10)	0.7248 (15)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0514 (7)	0.0583 (7)	0.0513 (7)	0.0136 (5)	0.0115 (5)	−0.0159 (5)
N2	0.0433 (7)	0.0436 (7)	0.0423 (7)	0.0067 (5)	0.0134 (6)	−0.0054 (5)
N1	0.0391 (7)	0.0411 (7)	0.0383 (6)	0.0041 (5)	0.0110 (5)	−0.0056 (5)
N3	0.0498 (8)	0.0483 (8)	0.0369 (7)	0.0048 (6)	0.0076 (6)	−0.0075 (6)
O2	0.0605 (7)	0.0436 (6)	0.0581 (7)	−0.0067 (5)	−0.0022 (6)	0.0069 (5)
C1	0.0409 (8)	0.0386 (8)	0.0364 (7)	0.0015 (6)	0.0110 (6)	0.0031 (6)
C11	0.0443 (8)	0.0376 (8)	0.0382 (8)	−0.0023 (6)	0.0146 (6)	0.0001 (6)
C7	0.0455 (9)	0.0397 (8)	0.0366 (7)	0.0017 (6)	0.0133 (6)	−0.0019 (6)
C16	0.0444 (8)	0.0530 (9)	0.0387 (8)	−0.0093 (7)	0.0152 (6)	−0.0092 (7)
C9	0.0433 (8)	0.0401 (8)	0.0386 (8)	0.0031 (6)	0.0121 (6)	−0.0018 (6)
C8	0.0418 (8)	0.0387 (8)	0.0374 (7)	0.0027 (6)	0.0121 (6)	−0.0009 (6)
C12	0.0489 (9)	0.0360 (8)	0.0382 (8)	−0.0027 (6)	0.0109 (6)	0.0002 (6)
C6	0.0474 (9)	0.0473 (9)	0.0405 (8)	0.0051 (7)	0.0117 (7)	−0.0017 (7)
C25	0.0466 (9)	0.0519 (9)	0.0459 (9)	−0.0101 (7)	0.0203 (7)	−0.0131 (7)
C17	0.0506 (10)	0.0646 (11)	0.0444 (9)	−0.0058 (8)	0.0143 (7)	−0.0030 (8)
C2	0.0461 (9)	0.0552 (9)	0.0449 (9)	0.0058 (7)	0.0135 (7)	−0.0019 (7)
C4	0.0436 (9)	0.0660 (11)	0.0511 (10)	−0.0024 (8)	0.0034 (7)	0.0071 (8)
C10	0.0495 (10)	0.0643 (11)	0.0533 (10)	0.0137 (8)	0.0139 (8)	−0.0075 (8)
C18	0.0556 (11)	0.0919 (15)	0.0382 (9)	−0.0157 (10)	0.0110 (8)	−0.0029 (9)
C24	0.0626 (11)	0.0551 (10)	0.0510 (10)	0.0013 (8)	0.0254 (8)	−0.0096 (8)
C5	0.0580 (10)	0.0540 (10)	0.0406 (8)	−0.0018 (8)	0.0055 (7)	−0.0039 (7)
C3	0.0446 (10)	0.0681 (11)	0.0546 (10)	0.0086 (8)	0.0131 (8)	0.0036 (9)
C19	0.0683 (12)	0.0818 (13)	0.0472 (10)	−0.0234 (10)	0.0239 (9)	−0.0240 (9)
C13	0.0486 (10)	0.0526 (10)	0.0580 (10)	−0.0104 (8)	0.0114 (8)	0.0019 (8)
C21	0.0903 (15)	0.0718 (13)	0.0745 (14)	−0.0120 (11)	0.0437 (12)	−0.0355 (11)
C20	0.0601 (11)	0.0620 (11)	0.0517 (10)	−0.0186 (8)	0.0260 (8)	−0.0205 (8)
C15	0.0667 (12)	0.0540 (10)	0.0559 (10)	0.0097 (9)	−0.0062 (9)	0.0075 (8)
C14	0.0471 (10)	0.0720 (12)	0.0595 (11)	0.0019 (9)	0.0053 (8)	0.0021 (9)
C23	0.0805 (14)	0.0602 (11)	0.0721 (12)	0.0112 (10)	0.0333 (11)	−0.0028 (10)
C22	0.1020 (17)	0.0592 (12)	0.0900 (16)	0.0080 (11)	0.0449 (13)	−0.0201 (11)

O1—C7	1.2483 (17)	C2—H2	0.9300
N2—C9	1.3074 (18)	C4—C3	1.377 (2)
N2—N1	1.4062 (16)	C4—C5	1.377 (2)
N1—C7	1.3787 (18)	C4—H4	0.9300
N1—C1	1.4181 (18)	C10—H10A	0.9600
N3—C11	1.3388 (19)	C10—H10B	0.9600
N3—C16	1.4251 (18)	C10—H10C	0.9600
N3—H3A	0.890 (17)	C18—C19	1.356 (3)
O2—C15	1.363 (2)	C18—H18	0.9300
O2—C12	1.3677 (17)	C24—C23	1.361 (2)
C1—C6	1.387 (2)	C24—H24	0.9300
C1—C2	1.390 (2)	C5—H5	0.9300
C11—C8	1.3928 (19)	C3—H3	0.9300
C11—C12	1.461 (2)	C19—C20	1.410 (3)
C7—C8	1.444 (2)	C19—H19	0.9300
C16—C17	1.370 (2)	C13—C14	1.421 (2)
C16—C25	1.430 (2)	C13—H13	0.9300
C9—C8	1.439 (2)	C21—C22	1.356 (3)
C9—C10	1.491 (2)	C21—C20	1.420 (3)
C12—C13	1.339 (2)	C21—H21	0.9300
C6—C5	1.380 (2)	C15—C14	1.316 (3)
C6—H6	0.9300	C15—H15	0.9300
C25—C24	1.414 (2)	C14—H14	0.9300
C25—C20	1.425 (2)	C23—C22	1.397 (3)
C17—C18	1.411 (2)	C23—H23	0.9300
C17—H17	0.9300	C22—H22	0.9300
C2—C3	1.382 (2)
C9—N2—N1	106.92 (11)	C5—C4—H4	120.6
C7—N1—N2	111.50 (11)	C9—C10—H10A	109.5
C7—N1—C1	129.74 (12)	C9—C10—H10B	109.5
N2—N1—C1	118.76 (11)	H10A—C10—H10B	109.5
C11—N3—C16	132.27 (14)	C9—C10—H10C	109.5
C11—N3—H3A	111.1 (11)	H10A—C10—H10C	109.5
C16—N3—H3A	114.8 (11)	H10B—C10—H10C	109.5
C15—O2—C12	106.02 (13)	C19—C18—C17	120.98 (17)
C6—C1—C2	119.41 (14)	C19—C18—H18	119.5
C6—C1—N1	119.62 (13)	C17—C18—H18	119.5
C2—C1—N1	120.92 (13)	C23—C24—C25	121.31 (16)
N3—C11—C8	117.99 (13)	C23—C24—H24	119.3
N3—C11—C12	120.57 (13)	C25—C24—H24	119.3
C8—C11—C12	121.43 (13)	C4—C5—C6	121.02 (16)
O1—C7—N1	126.48 (13)	C4—C5—H5	119.5
O1—C7—C8	128.64 (13)	C6—C5—H5	119.5
N1—C7—C8	104.88 (12)	C4—C3—C2	121.14 (16)
C17—C16—N3	123.69 (15)	C4—C3—H3	119.4
C17—C16—C25	120.68 (14)	C2—C3—H3	119.4
N3—C16—C25	115.34 (13)	C18—C19—C20	120.90 (16)
N2—C9—C8	111.25 (13)	C18—C19—H19	119.6
N2—C9—C10	119.01 (13)	C20—C19—H19	119.6
C8—C9—C10	129.61 (13)	C12—C13—C14	106.28 (15)
C11—C8—C9	132.15 (13)	C12—C13—H13	126.9
C11—C8—C7	122.51 (13)	C14—C13—H13	126.9
C9—C8—C7	105.33 (12)	C22—C21—C20	121.29 (17)
C13—C12—O2	109.92 (13)	C22—C21—H21	119.4
C13—C12—C11	134.89 (14)	C20—C21—H21	119.4
O2—C12—C11	115.19 (13)	C19—C20—C21	122.45 (16)
C5—C6—C1	119.89 (15)	C19—C20—C25	119.14 (17)
C5—C6—H6	120.1	C21—C20—C25	118.41 (17)
C1—C6—H6	120.1	C14—C15—O2	110.79 (15)
C24—C25—C20	118.23 (15)	C14—C15—H15	124.6
C24—C25—C16	123.42 (14)	O2—C15—H15	124.6
C20—C25—C16	118.34 (15)	C15—C14—C13	106.99 (16)
C16—C17—C18	119.84 (17)	C15—C14—H14	126.5
C16—C17—H17	120.1	C13—C14—H14	126.5
C18—C17—H17	120.1	C24—C23—C22	120.46 (19)
C3—C2—C1	119.63 (15)	C24—C23—H23	119.8
C3—C2—H2	120.2	C22—C23—H23	119.8
C1—C2—H2	120.2	C21—C22—C23	120.26 (19)
C3—C4—C5	118.90 (15)	C21—C22—H22	119.9
C3—C4—H4	120.6	C23—C22—H22	119.9
C9—N2—N1—C7	2.05 (16)	C2—C1—C6—C5	−1.3 (2)
C9—N2—N1—C1	−177.32 (12)	N1—C1—C6—C5	176.20 (14)
C7—N1—C1—C6	175.47 (14)	C17—C16—C25—C24	178.23 (15)
N2—N1—C1—C6	−5.3 (2)	N3—C16—C25—C24	−7.8 (2)
C7—N1—C1—C2	−7.0 (2)	C17—C16—C25—C20	−2.6 (2)
N2—N1—C1—C2	172.21 (13)	N3—C16—C25—C20	171.36 (14)
C16—N3—C11—C8	162.29 (15)	N3—C16—C17—C18	−173.62 (14)
C16—N3—C11—C12	−16.9 (3)	C25—C16—C17—C18	−0.1 (2)
N2—N1—C7—O1	176.89 (14)	C6—C1—C2—C3	1.1 (2)
C1—N1—C7—O1	−3.8 (3)	N1—C1—C2—C3	−176.36 (14)
N2—N1—C7—C8	−3.45 (15)	C16—C17—C18—C19	2.9 (3)
C1—N1—C7—C8	175.84 (13)	C20—C25—C24—C23	−1.0 (3)
C11—N3—C16—C17	−20.6 (3)	C16—C25—C24—C23	178.16 (17)
C11—N3—C16—C25	165.61 (16)	C3—C4—C5—C6	0.0 (3)
N1—N2—C9—C8	0.31 (17)	C1—C6—C5—C4	0.8 (2)
N1—N2—C9—C10	−175.88 (13)	C5—C4—C3—C2	−0.2 (3)
N3—C11—C8—C9	169.80 (15)	C1—C2—C3—C4	−0.4 (3)
C12—C11—C8—C9	−11.0 (3)	C17—C18—C19—C20	−2.8 (3)
N3—C11—C8—C7	−11.4 (2)	O2—C12—C13—C14	0.73 (19)
C12—C11—C8—C7	167.75 (14)	C11—C12—C13—C14	−179.64 (17)
N2—C9—C8—C11	176.57 (15)	C18—C19—C20—C21	179.81 (18)
C10—C9—C8—C11	−7.8 (3)	C18—C19—C20—C25	−0.1 (3)
N2—C9—C8—C7	−2.38 (17)	C22—C21—C20—C19	178.53 (19)
C10—C9—C8—C7	173.29 (16)	C22—C21—C20—C25	−1.6 (3)
O1—C7—C8—C11	4.0 (2)	C24—C25—C20—C19	−178.08 (15)
N1—C7—C8—C11	−175.66 (13)	C16—C25—C20—C19	2.7 (2)
O1—C7—C8—C9	−176.93 (16)	C24—C25—C20—C21	2.0 (2)
N1—C7—C8—C9	3.42 (15)	C16—C25—C20—C21	−177.14 (16)
C15—O2—C12—C13	−0.65 (19)	C12—O2—C15—C14	0.3 (2)
C15—O2—C12—C11	179.64 (14)	O2—C15—C14—C13	0.1 (2)
N3—C11—C12—C13	−57.2 (3)	C12—C13—C14—C15	−0.5 (2)
C8—C11—C12—C13	123.6 (2)	C25—C24—C23—C22	−0.6 (3)
N3—C11—C12—O2	122.37 (15)	C20—C21—C22—C23	0.0 (3)
C8—C11—C12—O2	−56.76 (19)	C24—C23—C22—C21	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.890 (17)	1.930 (17)	2.7030 (17)	144.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.890 (17)	1.930 (17)	2.7030 (17)	144.3 (16)