(Z)-4-[(3-Aminona-phthalen-2-yl-amino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

The mol-ecule of the title compound, C(27)H(22)N(4)O, 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 mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intra-molecular 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 = 418.49

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.07

3886 reflections

290 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034770/ff2079sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812034770/ff2079Isup3.cml

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

C27H22N4O	F(000) = 880
Mr = 418.49	Dx = 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

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

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(Fo2) + (0.0572P)2 + 0.1136P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3886 reflections	Δρmax = 0.19 e Å−3
290 parameters	Δρmin = −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)

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	0.27552 (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)*

	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)

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

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)

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) .