4-[(Z)-(2-Fur­yl)(2-naphthyl­amino)methyl­ene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Li, J.; Li, J.-Z.; Li, J.-Q.; Zhang, H.-Q.; Li, J.-M.

doi:10.1107/S1600536809025586

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1824

doi:10.1107/S1600536809025586

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ADDENDA AND ERRATA

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4-[(Z)-(2-Furyl)(2-naphthylamino)methylene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Jing Li,^a ^* Jin-Zhou Li,^a Jing-Qi Li,^a Heng-Qiang Zhang ^a and Jia-Min Li ^a

^aCollege of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025, People's Republic of China
^*Correspondence e-mail: lijinzhou20@163.com

(Received 26 June 2009; accepted 1 July 2009; online 11 July 2009)

The title compound, C₂₅H₁₉N₃O₂, crystallizes as discrete molecules which are well ordered through one intramolecular N—H⋯O hydrogen bond. Structural analysis indicates that the molecules 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_r = 393.43
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.120
S = 1.05
4755 reflections
276 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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)

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.

Supporting information

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

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

checkCIF report

Comment top

1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (HPMαFP), is a member of a family of 4-heterocyclic acylpyrazolones, first synthesized in 1983 (Dong et al., 1983). Such 4-heterocyclic acylpyrazolones derivatives was found to be useful as NMR shift-reagents (Mehrotra et al., 1978), and it is also important in understanding the behaviour of these compounds with respect to the mechanisms of pharmacological activities and physiological activities (Li et al., 2000). As part of this work, we synthesized the title compound (I) derived from HPMαFP, and its structure is reported here.

The molecular structure of (I) is shown in Fig. 1. The C(7)–O(1) distance is 1.248 (3)Å which is shorter than that for C–OH in some pyrazolone compounds 1.319 (5)Å (Uzoukwu et al., 1993) and 1.313 (2)Å (Holzer et al., 1999), whereas it is close to the distances for C=O in similar compounds: 1.256 (3)Å (Uzoukwu et al.,1993) and 1.254 (2) Å (Peng et al., 2004). The C(8)–C(11)(1.392 (8)Å) is shorter than the C–C (1.53 Å), but close to C–C in some correlative compounds,1.400 (4) Å (Chai et al., 2005). The C(11)–N(3) distances is 1.338 (8) Å, which is longer than the values of 1.292 Å (Peng et al., 2004) and 1.318 (3) Å (Lü et al., 2006) for C=N inpyrazolone compounds, but similar to that for C–N (1.339 Å) (Arıcı et al., 1999). So we conclude that the title compound exist in the keto-form in solid state. The N–H proton is strongly hydrogen bonded with the O(1) atom, the N(3)···O(1) distances is 2.7030 (2)Å and the angle of N(3)–H(3)···O(1) is 144.3 (16)°. Therefore, the crystal structure study shows that the compound exists in the amine-one form.

Related literature top

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 strectures, 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 top

All reagents were obtained from commercial sources and used without further purification. HPMαFP was synthesized according to the method proposed by Jensen (1959). A mixture of a 10 ml HPMαFP (1 mmol, 0.2683 g) anhydrous ethanol solution and 10 mlα-naphthylamine (1 mmol, 0.1432 g) ethanol solution was refluxed for 4–5 h at 75–80°C, a deep-yellow product which was precipitated, filtered off and washed with anhydrous ethanol for several times, dried in air. The deep-yellow powder was recrystallized from ethanol and the single crystals were obtained at room temperature after 3 days.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) (thermal ellipsoids are shown at 30% probability levels).

4-[(Z)-(2-furyl)(2-naphthylamino)methylene)]-3-methyl-1-phenyl- 1H-pyrazol-5(4H)-one top

Crystal data top

C₂₅H₁₉N₃O₂	F(000) = 824.0
M_r = 393.43	D_x = 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

Data collection top

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

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)] = 0.045	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(F_o²) + (0.05P)² + 0.2364P] where P = (F_o² + 2F_c²)/3
4755 reflections	(Δ/σ)_max = 0.001
276 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₁₉N₃O₂	V = 1983.5 (4) Å³
M_r = 393.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8484 (10) Å	µ = 0.09 mm⁻¹
b = 17.5071 (18) Å	T = 295 K
c = 12.1549 (13) Å	0.44 × 0.30 × 0.20 mm
β = 108.836 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4755 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	3166 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.983	R_int = 0.026
13952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.16 e Å⁻³
4755 reflections	Δρ_min = −0.18 e Å⁻³
276 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉N₃O₂
M_r	393.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.8484 (10), 17.5071 (18), 12.1549 (13)
β (°)	108.836 (2)
V (Å³)	1983.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.44 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2005)
T_min, T_max	0.959, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	13952, 4755, 3166
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.05
No. of reflections	4755
No. of parameters	276
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

The authors gratefully acknowledge financial support from the Scientific Research Foundation of the Education Department of Heilongjiang Province (grant No. 11521061), the Special Foundation of Creative Talents in Science and Technology of Harbin City (No. 2006RFXXG019) and the Foundation for Scientific and Technical Development of Harbin Normal University (No. 08XYG-12).

References

Arıcı, C., Tahir, M. N., Ülkü, D. & Atakol, O. (1999). Acta Cryst. C55, 1691–1692. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Dong, X.-C., Liu, F.-C. & Zhao, Y.-L. (1983). Acta Chim. Sin. 41, 848–852. CAS Google Scholar
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Peng, B., Liu, G., Liu, L., Jia, D. & Yu, K. (2004). J. Mol. Struct. 692, 217–222. Web of Science CSD CrossRef CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[(Z)-(2-Fur­yl)(2-naphthyl­amino)methyl­ene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(Z)-(2-Furyl)(2-naphthylamino)methylene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one