(Z)-4-[(3-Aminona­phthalen-2-yl­amino)(phen­yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zhang, Z.; Lü, X.; Zhao, S.; Liu, X.

doi:10.1107/S1600536812034770

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2777

doi:10.1107/S1600536812034770

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(Z)-4-[(3-Aminonaphthalen-2-ylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zhao Zhang,^a Xingqiang Lü,^a Shunsheng Zhao ^b and Xiangrong Liu ^b ^*

^aCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shannxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xian University of Science and Technology, Xi'an 710054, Shannxi, People's Republic of China
^*Correspondence e-mail: lvxq@nwu.edu.cn

(Received 1 August 2012; accepted 6 August 2012; online 25 August 2012)

The molecule of the title compound, C₂₇H₂₂N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 12.73 (11), 65.17 (6) and 49.82 (6)°, respectively, with the two benzene rings and the naphthalene ring system. In the crystal, pairs of molecules are linked by intermolecular N—H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intramolecular N—H⋯O hydrogen bond.

Related literature

For a related structure, see: Lu et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For the synthesis, see: Hennig & Mann (1988 ).

Experimental

Crystal data

C₂₇H₂₂N₄O
M_r = 418.49
Monoclinic, P 2₁ /n
a = 9.8052 (14) Å
b = 18.041 (3) Å
c = 13.2193 (18) Å
β = 110.797 (2)°
V = 2186.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.31 × 0.25 × 0.24 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.976, T_max = 0.981
10878 measured reflections
3886 independent reflections
2629 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.123
S = 1.07
3886 reflections
290 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.06	2.7196 (19)	133
N4—H4A⋯N2ⁱ	0.92 (2)	2.21 (2)	3.121 (2)	169.8 (18)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536812034770/ff2079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034770/ff2079Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034770/ff2079Isup3.cml

checkCIF report

Comment top

Asymmetric Schiff bases attract the interest of researchers because they can form complexes with most of transition metal ions. These Schiff base complexes show excellent catalytic activity and selectivity in various reactions. Here we report the crystal structure of a novel asymmetrical Schiff base ligand (I) (Fig. 1). Bond lengths are in the range of normal values (Allen et al., 1987) and are comparable to those observed in similar compounds (Lu et al., 2011). The molecules of the title compound are linked by N—H···N hydrogen to form molecular pairs (Fig. 2). An intramolecular N3—H3a···O1 hydrogen bond forms an S6 ring motif.

Related literature top

For a related structure, see: Lu et al. (2011). For bond-length data, see: Allen et al. (1987). For the synthesis, see: Hennig & Mann (1988).

Experimental top

The title compound was obtained according to the synthetic procedure of Hennig & Mann (1988) with some modification. 2,3-diaminonaphthalene and 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one were refluxed for 2 h in a molar ratio of 1:1 in absolute ethanol to give the product. The single-crystal of suitable for X-ray diffraction was obtained by slow evaporation of its ethanolic solution of the title compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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

The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

The packing of (I), showing molecules connected by N—H···N hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.

(Z)-4-[(3-Aminonaphthalen-2-ylamino)(phenyl)methylidene]- 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₇H₂₂N₄O	F(000) = 880
M_r = 418.49	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4488 reflections
a = 9.8052 (14) Å	θ = 1.9–25.1°
b = 18.041 (3) Å	µ = 0.08 mm⁻¹
c = 13.2193 (18) Å	T = 296 K
β = 110.797 (2)°	Block, red
V = 2186.0 (5) Å³	0.31 × 0.25 × 0.24 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3886 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
thin–slice ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
T_min = 0.976, T_max = 0.981	k = −21→15
10878 measured reflections	l = −15→14

Refinement top

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0572P)² + 0.1136P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3886 reflections	Δρ_max = 0.19 e Å⁻³
290 parameters	Δρ_min = −0.13 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: 0.0046 (10)

Crystal data top

C₂₇H₂₂N₄O	V = 2186.0 (5) Å³
M_r = 418.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8052 (14) Å	µ = 0.08 mm⁻¹
b = 18.041 (3) Å	T = 296 K
c = 13.2193 (18) Å	0.31 × 0.25 × 0.24 mm
β = 110.797 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3886 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2629 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.027
10878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.19 e Å⁻³
3886 reflections	Δρ_min = −0.13 e Å⁻³
290 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	0.27552 (14)	1.00646 (7)	0.55789 (10)	0.0609 (4)
N2	0.43043 (16)	0.85291 (8)	0.47774 (12)	0.0549 (4)
N1	0.31277 (16)	0.89991 (8)	0.46993 (11)	0.0516 (4)
N3	0.51820 (16)	1.03547 (8)	0.73333 (11)	0.0540 (4)
H3A	0.4486	1.0534	0.6789	0.065*
C18	0.55379 (19)	1.07787 (9)	0.82950 (14)	0.0490 (4)
C26	0.5429 (2)	1.19826 (10)	0.90501 (15)	0.0556 (5)
H26A	0.5190	1.2483	0.8961	0.067*
C27	0.52031 (19)	1.15528 (10)	0.81475 (14)	0.0500 (4)
C25	0.60116 (19)	1.16913 (10)	1.01105 (15)	0.0523 (5)
C12	0.71102 (19)	0.94103 (9)	0.79235 (13)	0.0476 (4)
C11	0.57512 (19)	0.97179 (9)	0.71287 (14)	0.0482 (4)
C8	0.50078 (19)	0.93546 (9)	0.61583 (13)	0.0481 (4)
C5	0.1637 (2)	0.83859 (9)	0.30338 (14)	0.0541 (5)
H5A	0.2457	0.8137	0.3014	0.065*
C6	0.1758 (2)	0.88711 (9)	0.38791 (14)	0.0488 (4)
C7	0.3538 (2)	0.95422 (10)	0.54880 (13)	0.0495 (4)
N4	0.4582 (2)	1.18265 (11)	0.71068 (14)	0.0656 (5)
C19	0.60730 (19)	1.04834 (10)	0.93090 (14)	0.0532 (5)
H19A	0.6266	0.9978	0.9389	0.064*
C20	0.63419 (19)	1.09256 (10)	1.02421 (14)	0.0504 (5)
C21	0.6924 (2)	1.06300 (11)	1.12955 (15)	0.0616 (5)
H21A	0.7117	1.0125	1.1385	0.074*
C3	−0.0920 (2)	0.86374 (11)	0.22376 (17)	0.0646 (5)
H3B	−0.1812	0.8567	0.1681	0.078*
C9	0.5400 (2)	0.87347 (9)	0.56375 (14)	0.0507 (5)
C13	0.7088 (2)	0.87261 (10)	0.83947 (15)	0.0612 (5)
H13A	0.6213	0.8469	0.8229	0.073*
C1	0.0515 (2)	0.92247 (10)	0.38980 (15)	0.0606 (5)
H1A	0.0572	0.9545	0.4463	0.073*
C23	0.6896 (2)	1.18263 (13)	1.20526 (17)	0.0721 (6)
H23A	0.7097	1.2127	1.2659	0.087*
C4	0.0309 (2)	0.82743 (10)	0.22284 (15)	0.0610 (5)
H4C	0.0239	0.7948	0.1668	0.073*
C24	0.6299 (2)	1.21312 (11)	1.10469 (16)	0.0646 (5)
H24A	0.6079	1.2634	1.0977	0.077*
C17	0.8418 (2)	0.97844 (11)	0.81943 (16)	0.0638 (5)
H17A	0.8446	1.0250	0.7900	0.077*
C10	0.6841 (2)	0.83662 (11)	0.58793 (16)	0.0651 (6)
H10A	0.6744	0.7966	0.5379	0.098*
H10B	0.7172	0.8175	0.6604	0.098*
H10C	0.7535	0.8720	0.5810	0.098*
C22	0.7211 (2)	1.10693 (12)	1.21862 (16)	0.0671 (6)
H22A	0.7613	1.0867	1.2876	0.081*
C2	−0.0809 (2)	0.91046 (11)	0.30816 (17)	0.0660 (6)
H2B	−0.1638	0.9344	0.3104	0.079*
C14	0.8356 (3)	0.84252 (11)	0.91075 (16)	0.0726 (6)
H14A	0.8332	0.7969	0.9430	0.087*
C16	0.9680 (2)	0.94749 (14)	0.88954 (18)	0.0805 (6)
H16A	1.0559	0.9729	0.9067	0.097*
C15	0.9647 (3)	0.87940 (14)	0.93425 (18)	0.0787 (6)
H15A	1.0506	0.8582	0.9807	0.094*
H4A	0.497 (2)	1.1671 (11)	0.6603 (17)	0.083 (7)*
H4B	0.436 (3)	1.2320 (14)	0.7045 (17)	0.098 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0635 (9)	0.0555 (8)	0.0600 (8)	0.0159 (6)	0.0173 (7)	−0.0065 (6)
N2	0.0542 (10)	0.0522 (9)	0.0562 (10)	0.0090 (7)	0.0168 (8)	−0.0072 (7)
N1	0.0522 (10)	0.0506 (9)	0.0494 (9)	0.0094 (7)	0.0147 (8)	−0.0073 (7)
N3	0.0600 (10)	0.0483 (9)	0.0482 (9)	0.0088 (7)	0.0124 (8)	−0.0048 (7)
C18	0.0474 (11)	0.0483 (10)	0.0510 (11)	−0.0011 (8)	0.0171 (9)	−0.0080 (8)
C26	0.0581 (12)	0.0463 (10)	0.0633 (12)	0.0025 (8)	0.0227 (10)	−0.0054 (9)
C27	0.0468 (11)	0.0509 (11)	0.0529 (11)	0.0013 (8)	0.0183 (9)	−0.0017 (9)
C25	0.0474 (11)	0.0527 (11)	0.0585 (12)	−0.0064 (8)	0.0211 (9)	−0.0085 (9)
C12	0.0521 (11)	0.0445 (10)	0.0469 (10)	0.0020 (8)	0.0183 (9)	−0.0022 (8)
C11	0.0522 (11)	0.0445 (10)	0.0504 (11)	0.0006 (8)	0.0213 (9)	0.0009 (8)
C8	0.0530 (11)	0.0444 (10)	0.0453 (10)	0.0053 (8)	0.0156 (9)	−0.0016 (8)
C5	0.0588 (13)	0.0497 (11)	0.0527 (11)	0.0026 (9)	0.0183 (10)	−0.0022 (9)
C6	0.0525 (11)	0.0461 (10)	0.0467 (10)	0.0015 (8)	0.0160 (9)	0.0030 (8)
C7	0.0591 (12)	0.0476 (10)	0.0438 (10)	0.0048 (9)	0.0208 (9)	−0.0003 (8)
N4	0.0803 (13)	0.0607 (12)	0.0561 (11)	0.0229 (9)	0.0246 (10)	0.0045 (9)
C19	0.0566 (12)	0.0461 (10)	0.0570 (12)	0.0013 (8)	0.0205 (10)	−0.0016 (9)
C20	0.0452 (11)	0.0538 (11)	0.0527 (11)	−0.0046 (8)	0.0180 (9)	−0.0050 (9)
C21	0.0644 (13)	0.0646 (13)	0.0579 (12)	−0.0017 (10)	0.0245 (10)	−0.0017 (10)
C3	0.0579 (13)	0.0642 (13)	0.0609 (13)	−0.0016 (10)	0.0078 (10)	0.0031 (10)
C9	0.0551 (12)	0.0476 (10)	0.0488 (11)	0.0056 (8)	0.0175 (10)	0.0000 (8)
C13	0.0642 (13)	0.0487 (11)	0.0619 (13)	−0.0055 (9)	0.0115 (10)	0.0026 (10)
C1	0.0603 (13)	0.0642 (12)	0.0562 (12)	0.0064 (10)	0.0192 (11)	−0.0059 (10)
C23	0.0765 (16)	0.0817 (16)	0.0611 (14)	−0.0114 (12)	0.0280 (12)	−0.0202 (12)
C4	0.0683 (14)	0.0551 (12)	0.0541 (12)	−0.0011 (10)	0.0150 (11)	−0.0044 (9)
C24	0.0716 (14)	0.0604 (12)	0.0640 (14)	−0.0069 (10)	0.0269 (11)	−0.0162 (10)
C17	0.0571 (13)	0.0641 (12)	0.0697 (14)	−0.0029 (10)	0.0219 (11)	0.0122 (10)
C10	0.0588 (13)	0.0683 (13)	0.0659 (13)	0.0173 (10)	0.0191 (11)	−0.0072 (10)
C22	0.0686 (14)	0.0826 (16)	0.0513 (12)	−0.0031 (11)	0.0226 (11)	−0.0023 (11)
C2	0.0564 (13)	0.0692 (13)	0.0690 (14)	0.0094 (10)	0.0183 (11)	0.0023 (11)
C14	0.0867 (18)	0.0538 (12)	0.0636 (14)	0.0054 (11)	0.0098 (12)	0.0096 (10)
C16	0.0520 (14)	0.0979 (18)	0.0852 (16)	−0.0040 (12)	0.0167 (12)	0.0146 (14)
C15	0.0643 (15)	0.0876 (17)	0.0703 (15)	0.0164 (12)	0.0065 (12)	0.0072 (13)

Geometric parameters (Å, º) top

O1—C7	1.2480 (19)	C19—H19A	0.9300
N2—C9	1.310 (2)	C20—C21	1.409 (2)
N2—N1	1.4056 (19)	C21—C22	1.363 (3)
N1—C7	1.382 (2)	C21—H21A	0.9300
N1—C6	1.414 (2)	C3—C2	1.371 (3)
N3—C11	1.346 (2)	C3—C4	1.376 (3)
N3—C18	1.417 (2)	C3—H3B	0.9300
N3—H3A	0.8600	C9—C10	1.490 (2)
C18—C19	1.362 (2)	C13—C14	1.377 (3)
C18—C27	1.432 (2)	C13—H13A	0.9300
C26—C27	1.373 (2)	C1—C2	1.379 (3)
C26—C25	1.414 (2)	C1—H1A	0.9300
C26—H26A	0.9300	C23—C24	1.364 (3)
C27—N4	1.383 (2)	C23—C22	1.398 (3)
C25—C24	1.412 (2)	C23—H23A	0.9300
C25—C20	1.415 (2)	C4—H4C	0.9300
C12—C17	1.379 (3)	C24—H24A	0.9300
C12—C13	1.386 (2)	C17—C16	1.374 (3)
C12—C11	1.481 (2)	C17—H17A	0.9300
C11—C8	1.394 (2)	C10—H10A	0.9600
C8—C9	1.436 (2)	C10—H10B	0.9600
C8—C7	1.439 (2)	C10—H10C	0.9600
C5—C4	1.373 (3)	C22—H22A	0.9300
C5—C6	1.391 (2)	C2—H2B	0.9300
C5—H5A	0.9300	C14—C15	1.365 (3)
C6—C1	1.384 (2)	C14—H14A	0.9300
N4—H4A	0.92 (2)	C16—C15	1.368 (3)
N4—H4B	0.91 (2)	C16—H16A	0.9300
C19—C20	1.413 (2)	C15—H15A	0.9300

C9—N2—N1	106.96 (14)	C22—C21—H21A	119.3
C7—N1—N2	111.14 (15)	C20—C21—H21A	119.3
C7—N1—C6	129.56 (14)	C2—C3—C4	118.88 (19)
N2—N1—C6	119.30 (14)	C2—C3—H3B	120.6
C11—N3—C18	130.80 (15)	C4—C3—H3B	120.6
C11—N3—H3A	114.6	N2—C9—C8	111.09 (16)
C18—N3—H3A	114.6	N2—C9—C10	118.87 (16)
C19—C18—N3	123.89 (15)	C8—C9—C10	129.78 (17)
C19—C18—C27	120.33 (16)	C14—C13—C12	120.25 (19)
N3—C18—C27	115.64 (15)	C14—C13—H13A	119.9
C27—C26—C25	122.37 (16)	C12—C13—H13A	119.9
C27—C26—H26A	118.8	C2—C1—C6	120.25 (18)
C25—C26—H26A	118.8	C2—C1—H1A	119.9
C26—C27—N4	122.76 (17)	C6—C1—H1A	119.9
C26—C27—C18	118.27 (16)	C24—C23—C22	121.09 (19)
N4—C27—C18	118.84 (16)	C24—C23—H23A	119.5
C24—C25—C26	123.02 (17)	C22—C23—H23A	119.5
C24—C25—C20	118.36 (17)	C5—C4—C3	121.06 (18)
C26—C25—C20	118.61 (16)	C5—C4—H4C	119.5
C17—C12—C13	118.74 (18)	C3—C4—H4C	119.5
C17—C12—C11	121.35 (16)	C23—C24—C25	120.72 (19)
C13—C12—C11	119.90 (16)	C23—C24—H24A	119.6
N3—C11—C8	117.88 (16)	C25—C24—H24A	119.6
N3—C11—C12	120.67 (15)	C16—C17—C12	120.53 (19)
C8—C11—C12	121.44 (15)	C16—C17—H17A	119.7
C11—C8—C9	131.77 (17)	C12—C17—H17A	119.7
C11—C8—C7	122.58 (15)	C9—C10—H10A	109.5
C9—C8—C7	105.55 (15)	C9—C10—H10B	109.5
C4—C5—C6	120.14 (17)	H10A—C10—H10B	109.5
C4—C5—H5A	119.9	C9—C10—H10C	109.5
C6—C5—H5A	119.9	H10A—C10—H10C	109.5
C1—C6—C5	118.70 (18)	H10B—C10—H10C	109.5
C1—C6—N1	120.94 (16)	C21—C22—C23	119.4 (2)
C5—C6—N1	120.37 (15)	C21—C22—H22A	120.3
O1—C7—N1	125.71 (17)	C23—C22—H22A	120.3
O1—C7—C8	129.36 (16)	C3—C2—C1	120.95 (19)
N1—C7—C8	104.92 (14)	C3—C2—H2B	119.5
C27—N4—H4A	117.6 (13)	C1—C2—H2B	119.5
C27—N4—H4B	116.4 (14)	C15—C14—C13	120.2 (2)
H4A—N4—H4B	112.3 (19)	C15—C14—H14A	119.9
C18—C19—C20	121.69 (16)	C13—C14—H14A	119.9
C18—C19—H19A	119.2	C15—C16—C17	120.2 (2)
C20—C19—H19A	119.2	C15—C16—H16A	119.9
C21—C20—C19	122.25 (17)	C17—C16—H16A	119.9
C21—C20—C25	119.06 (16)	C14—C15—C16	120.1 (2)
C19—C20—C25	118.69 (16)	C14—C15—H15A	120.0
C22—C21—C20	121.36 (19)	C16—C15—H15A	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.06	2.7196 (19)	133
N4—H4A···N2ⁱ	0.92 (2)	2.21 (2)	3.121 (2)	169.8 (18)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₂N₄O
M_r	418.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.8052 (14), 18.041 (3), 13.2193 (18)
β (°)	110.797 (2)
V (Å³)	2186.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.25 × 0.24

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	10878, 3886, 2629
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.123, 1.07
No. of reflections	3886
No. of parameters	290
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
N3—H3A···O1	0.86	2.06	2.7196 (19)	133.3
N4—H4A···N2ⁱ	0.92 (2)	2.21 (2)	3.121 (2)	169.8 (18)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

The project was supported by the National Natural Science Foundation of China (program Nos. 21103135, 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011) and the Scientific Research Program Funded by Shaanxi Provincial Education Department (program No.12 J K0622).

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 (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hennig, L. & Mann, G. (1988). Z. Chem. 28, 364-365. CrossRef CAS Google Scholar
Lu, R., Xia, H., Lü, X. & Zhao, S. (2011). Acta Cryst. E67, o2701. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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

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Volume 68| Part 9| September 2012| Page o2777

doi:10.1107/S1600536812034770

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

(Z)-4-[(3-Aminona­phthalen-2-yl­amino)(phen­yl)methyl­­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

(Z)-4-[(3-Aminonaphthalen-2-ylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one