4-[(Anthracen-9-yl-methyl-idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

In the title compound, C(26)H(21)N(3)O, the phenyl ring of the 4-amino-anti-pyrine group and the heterocyclic five-membered ring along with its substituents, except for the N-bound methyl group (r.m.s. deviation = 0.0027 Å), form a dihedral angle of 54.20 (5)°. Two S(6) ring motifs are formed due to intra-molecular C-H⋯N and C-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked into supra-molecular chains along the a-axis direction via C-H⋯O contacts.

Related literature

For background to pyrazol-3-ones, see: Asiri & Khan (2010 ▶); Crane et al. (1985 ▶); Desai et al. (2010 ▶); Rai et al. (2009 ▶); Takagi et al. (1987 ▶); Yao et al. (2007 ▶); Zhang et al. (2005 ▶); For related crystal structures, see: Li & Zhang (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H21N3O

M = 391.46

Monoclinic,

a = 7.6603 (3) Å

b = 16.4549 (6) Å

c = 15.8849 (6) Å

β = 95.243 (1)°

V = 1993.91 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.980

14673 measured reflections

3593 independent reflections

2791 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.06

3593 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029126/tk2768sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029126/tk2768Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029126/tk2768Isup3.cml

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

C26H21N3O	F(000) = 824
Mr = 391.46	Dx = 1.304 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2791 reflections
a = 7.6603 (3) Å	θ = 2.8–25.3°
b = 16.4549 (6) Å	µ = 0.08 mm−1
c = 15.8849 (6) Å	T = 296 K
β = 95.243 (1)°	Prism, yellow
V = 1993.91 (13) Å3	0.32 × 0.24 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3593 independent reflections
Radiation source: fine-focus sealed tube	2791 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→19
Tmin = 0.975, Tmax = 0.980	l = −19→19
14673 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.4551P] where P = (Fo2 + 2Fc2)/3
3593 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.30051 (14)	0.39403 (7)	0.06517 (7)	0.0520 (4)
N1	0.56061 (17)	0.42547 (8)	0.22734 (8)	0.0409 (4)
N2	0.74133 (15)	0.37942 (7)	0.03382 (7)	0.0359 (4)
N3	0.56279 (15)	0.38171 (8)	0.00463 (8)	0.0383 (4)
C1	0.46213 (19)	0.39626 (9)	0.07155 (9)	0.0367 (5)
C2	0.58906 (19)	0.41001 (9)	0.14336 (9)	0.0359 (5)
C3	0.75240 (19)	0.40245 (8)	0.11629 (9)	0.0348 (5)
C4	0.9234 (2)	0.42095 (10)	0.16435 (10)	0.0465 (6)
C5	0.8631 (2)	0.40778 (10)	−0.02533 (10)	0.0441 (5)
C6	0.50243 (18)	0.34201 (9)	−0.07195 (9)	0.0352 (5)
C7	0.5734 (2)	0.26909 (10)	−0.09414 (10)	0.0460 (5)
C8	0.5114 (3)	0.23253 (12)	−0.16899 (12)	0.0600 (7)
C9	0.3794 (3)	0.26782 (13)	−0.22057 (12)	0.0624 (7)
C10	0.3093 (3)	0.34023 (12)	−0.19815 (11)	0.0574 (6)
C11	0.3707 (2)	0.37817 (10)	−0.12373 (10)	0.0457 (5)
C12	0.4106 (2)	0.44921 (10)	0.24467 (10)	0.0442 (5)
C13	0.36155 (19)	0.46454 (9)	0.33093 (9)	0.0396 (5)
C14	0.40579 (19)	0.41027 (9)	0.39838 (9)	0.0391 (5)
C15	0.5113 (2)	0.33949 (10)	0.39171 (11)	0.0461 (6)
C16	0.5522 (2)	0.29004 (11)	0.45886 (11)	0.0527 (6)
C17	0.4888 (2)	0.30582 (12)	0.53761 (11)	0.0551 (7)
C18	0.3861 (2)	0.37129 (11)	0.54708 (10)	0.0511 (6)
C19	0.3405 (2)	0.42567 (10)	0.47887 (10)	0.0427 (5)
C20	0.2374 (2)	0.49383 (10)	0.48880 (11)	0.0477 (5)
C21	0.1963 (2)	0.54873 (10)	0.42364 (11)	0.0455 (5)
C22	0.0966 (2)	0.62024 (11)	0.43539 (13)	0.0570 (7)
C23	0.0667 (3)	0.67545 (12)	0.37312 (15)	0.0661 (7)
C24	0.1354 (3)	0.66362 (12)	0.29507 (14)	0.0648 (7)
C25	0.2282 (2)	0.59577 (11)	0.28014 (12)	0.0542 (6)
C26	0.2605 (2)	0.53462 (10)	0.34333 (10)	0.0423 (5)
H4A	1.00701	0.37971	0.15337	0.0698*
H4B	0.90884	0.42224	0.22373	0.0698*
H4C	0.96475	0.47284	0.14700	0.0698*
H5A	0.83578	0.46297	−0.04108	0.0661*
H5B	0.85281	0.37406	−0.07485	0.0661*
H5C	0.98079	0.40495	0.00106	0.0661*
H7	0.66211	0.24477	−0.05898	0.0552*
H8	0.55952	0.18352	−0.18466	0.0720*
H9	0.33756	0.24253	−0.27077	0.0749*
H10	0.21973	0.36406	−0.23322	0.0689*
H11	0.32363	0.42763	−0.10874	0.0548*
H12	0.32552	0.45754	0.19988	0.0530*
H15	0.55291	0.32700	0.34006	0.0554*
H16	0.62332	0.24500	0.45278	0.0632*
H17	0.51757	0.27122	0.58306	0.0661*
H18	0.34431	0.38108	0.59928	0.0614*
H20	0.19451	0.50300	0.54088	0.0572*
H22	0.05130	0.62897	0.48699	0.0683*
H23	0.00031	0.72151	0.38185	0.0793*
H24	0.11711	0.70285	0.25306	0.0778*
H25	0.27146	0.58896	0.22778	0.0650*

	U11	U22	U33	U12	U13	U23
O1	0.0282 (6)	0.0734 (8)	0.0544 (7)	0.0007 (5)	0.0042 (5)	−0.0123 (6)
N1	0.0352 (7)	0.0483 (8)	0.0397 (7)	−0.0023 (6)	0.0060 (5)	−0.0023 (6)
N2	0.0254 (6)	0.0435 (7)	0.0390 (7)	−0.0014 (5)	0.0037 (5)	−0.0011 (5)
N3	0.0274 (7)	0.0475 (8)	0.0399 (7)	−0.0002 (5)	0.0020 (5)	−0.0062 (5)
C1	0.0292 (8)	0.0389 (9)	0.0425 (8)	−0.0003 (6)	0.0054 (6)	−0.0030 (6)
C2	0.0323 (8)	0.0381 (8)	0.0376 (8)	−0.0003 (6)	0.0050 (6)	−0.0008 (6)
C3	0.0317 (8)	0.0339 (8)	0.0386 (8)	−0.0001 (6)	0.0024 (6)	0.0032 (6)
C4	0.0322 (9)	0.0613 (11)	0.0454 (9)	−0.0030 (7)	−0.0004 (7)	0.0024 (8)
C5	0.0355 (9)	0.0536 (10)	0.0442 (9)	−0.0064 (7)	0.0099 (7)	0.0016 (7)
C6	0.0308 (8)	0.0383 (8)	0.0368 (8)	−0.0049 (6)	0.0042 (6)	0.0000 (6)
C7	0.0417 (9)	0.0468 (9)	0.0483 (9)	0.0043 (7)	−0.0025 (7)	−0.0027 (7)
C8	0.0597 (12)	0.0573 (11)	0.0612 (11)	0.0043 (9)	−0.0037 (9)	−0.0193 (9)
C9	0.0607 (12)	0.0750 (14)	0.0493 (11)	−0.0072 (10)	−0.0068 (9)	−0.0173 (9)
C10	0.0524 (11)	0.0669 (12)	0.0500 (10)	0.0003 (9)	−0.0115 (8)	0.0050 (9)
C11	0.0429 (9)	0.0444 (9)	0.0488 (10)	0.0022 (7)	−0.0009 (7)	0.0019 (7)
C12	0.0365 (9)	0.0544 (10)	0.0413 (9)	0.0018 (7)	0.0014 (7)	−0.0063 (7)
C13	0.0305 (8)	0.0477 (9)	0.0410 (8)	−0.0048 (7)	0.0049 (6)	−0.0077 (7)
C14	0.0310 (8)	0.0445 (9)	0.0420 (8)	−0.0087 (7)	0.0043 (6)	−0.0078 (7)
C15	0.0422 (10)	0.0484 (10)	0.0481 (9)	−0.0030 (7)	0.0056 (7)	−0.0069 (7)
C16	0.0457 (10)	0.0494 (10)	0.0623 (11)	−0.0039 (8)	0.0010 (8)	0.0002 (8)
C17	0.0486 (11)	0.0597 (12)	0.0555 (11)	−0.0140 (9)	−0.0029 (8)	0.0105 (9)
C18	0.0471 (10)	0.0657 (12)	0.0410 (9)	−0.0189 (9)	0.0064 (7)	−0.0024 (8)
C19	0.0352 (9)	0.0499 (10)	0.0436 (9)	−0.0138 (7)	0.0063 (7)	−0.0070 (7)
C20	0.0398 (9)	0.0580 (10)	0.0477 (9)	−0.0128 (8)	0.0173 (7)	−0.0150 (8)
C21	0.0317 (8)	0.0487 (10)	0.0572 (10)	−0.0086 (7)	0.0109 (7)	−0.0131 (8)
C22	0.0396 (10)	0.0558 (11)	0.0774 (13)	−0.0030 (8)	0.0159 (9)	−0.0201 (10)
C23	0.0450 (11)	0.0522 (11)	0.1008 (16)	0.0055 (9)	0.0058 (10)	−0.0150 (11)
C24	0.0511 (12)	0.0590 (12)	0.0829 (14)	0.0060 (9)	−0.0016 (10)	0.0047 (10)
C25	0.0443 (10)	0.0623 (11)	0.0554 (10)	0.0036 (8)	0.0015 (8)	−0.0019 (9)
C26	0.0295 (8)	0.0487 (9)	0.0489 (9)	−0.0042 (7)	0.0041 (7)	−0.0081 (7)

O1—C1	1.2335 (18)	C21—C22	1.424 (2)
N1—C2	1.3946 (19)	C21—C26	1.428 (2)
N1—C12	1.268 (2)	C22—C23	1.347 (3)
N2—N3	1.4039 (16)	C23—C24	1.404 (3)
N2—C3	1.3589 (18)	C24—C25	1.356 (3)
N2—C5	1.4598 (19)	C25—C26	1.427 (2)
N3—C1	1.3899 (19)	C4—H4A	0.9600
N3—C6	1.4204 (19)	C4—H4B	0.9600
C1—C2	1.447 (2)	C4—H4C	0.9600
C2—C3	1.365 (2)	C5—H5A	0.9600
C3—C4	1.486 (2)	C5—H5B	0.9600
C6—C7	1.376 (2)	C5—H5C	0.9600
C6—C11	1.377 (2)	C7—H7	0.9300
C7—C8	1.378 (3)	C8—H8	0.9300
C8—C9	1.371 (3)	C9—H9	0.9300
C9—C10	1.367 (3)	C10—H10	0.9300
C10—C11	1.381 (2)	C11—H11	0.9300
C12—C13	1.475 (2)	C12—H12	0.9300
C13—C14	1.412 (2)	C15—H15	0.9300
C13—C26	1.413 (2)	C16—H16	0.9300
C14—C15	1.427 (2)	C17—H17	0.9300
C14—C19	1.437 (2)	C18—H18	0.9300
C15—C16	1.355 (2)	C20—H20	0.9300
C16—C17	1.407 (2)	C22—H22	0.9300
C17—C18	1.351 (3)	C23—H23	0.9300
C18—C19	1.424 (2)	C24—H24	0.9300
C19—C20	1.389 (2)	C25—H25	0.9300
C20—C21	1.388 (2)
C2—N1—C12	119.21 (13)	C13—C26—C21	119.69 (14)
N3—N2—C3	106.50 (11)	C13—C26—C25	122.66 (14)
N3—N2—C5	116.06 (11)	C21—C26—C25	117.53 (15)
C3—N2—C5	122.96 (12)	C3—C4—H4A	109.00
N2—N3—C1	110.11 (11)	C3—C4—H4B	109.00
N2—N3—C6	120.10 (11)	C3—C4—H4C	109.00
C1—N3—C6	125.05 (12)	H4A—C4—H4B	109.00
O1—C1—N3	123.70 (13)	H4A—C4—H4C	109.00
O1—C1—C2	131.78 (14)	H4B—C4—H4C	109.00
N3—C1—C2	104.48 (12)	N2—C5—H5A	109.00
N1—C2—C1	129.04 (13)	N2—C5—H5B	109.00
N1—C2—C3	123.07 (13)	N2—C5—H5C	109.00
C1—C2—C3	107.85 (13)	H5A—C5—H5B	109.00
N2—C3—C2	110.53 (13)	H5A—C5—H5C	109.00
N2—C3—C4	121.79 (13)	H5B—C5—H5C	109.00
C2—C3—C4	127.56 (13)	C6—C7—H7	120.00
N3—C6—C7	121.00 (13)	C8—C7—H7	120.00
N3—C6—C11	118.43 (13)	C7—C8—H8	120.00
C7—C6—C11	120.57 (14)	C9—C8—H8	120.00
C6—C7—C8	119.25 (15)	C8—C9—H9	120.00
C7—C8—C9	120.54 (18)	C10—C9—H9	120.00
C8—C9—C10	119.95 (18)	C9—C10—H10	120.00
C9—C10—C11	120.38 (18)	C11—C10—H10	120.00
C6—C11—C10	119.31 (16)	C6—C11—H11	120.00
N1—C12—C13	124.56 (14)	C10—C11—H11	120.00
C12—C13—C14	122.19 (13)	N1—C12—H12	118.00
C12—C13—C26	117.28 (13)	C13—C12—H12	118.00
C14—C13—C26	120.47 (13)	C14—C15—H15	119.00
C13—C14—C15	123.92 (14)	C16—C15—H15	119.00
C13—C14—C19	118.98 (13)	C15—C16—H16	119.00
C15—C14—C19	117.09 (14)	C17—C16—H16	120.00
C14—C15—C16	121.55 (15)	C16—C17—H17	120.00
C15—C16—C17	121.01 (16)	C18—C17—H17	120.00
C16—C17—C18	119.88 (16)	C17—C18—H18	119.00
C17—C18—C19	121.43 (15)	C19—C18—H18	119.00
C14—C19—C18	119.01 (14)	C19—C20—H20	119.00
C14—C19—C20	119.41 (15)	C21—C20—H20	119.00
C18—C19—C20	121.57 (15)	C21—C22—H22	119.00
C19—C20—C21	122.23 (15)	C23—C22—H22	119.00
C20—C21—C22	121.85 (16)	C22—C23—H23	120.00
C20—C21—C26	119.16 (15)	C24—C23—H23	120.00
C22—C21—C26	118.95 (16)	C23—C24—H24	120.00
C21—C22—C23	121.21 (18)	C25—C24—H24	120.00
C22—C23—C24	120.17 (19)	C24—C25—H25	119.00
C23—C24—C25	120.89 (19)	C26—C25—H25	119.00
C24—C25—C26	121.17 (17)
C12—N1—C2—C1	−17.9 (2)	N1—C12—C13—C26	137.66 (17)
C12—N1—C2—C3	164.62 (15)	C12—C13—C14—C15	4.7 (2)
C2—N1—C12—C13	177.51 (14)	C12—C13—C14—C19	−174.64 (14)
C3—N2—N3—C1	−7.39 (15)	C26—C13—C14—C15	−178.17 (15)
C3—N2—N3—C6	−164.20 (12)	C26—C13—C14—C19	2.5 (2)
C5—N2—N3—C1	−148.34 (13)	C12—C13—C26—C21	174.53 (14)
C5—N2—N3—C6	54.85 (17)	C12—C13—C26—C25	−9.7 (2)
N3—N2—C3—C2	7.04 (15)	C14—C13—C26—C21	−2.8 (2)
N3—N2—C3—C4	−169.32 (13)	C14—C13—C26—C25	173.05 (15)
C5—N2—C3—C2	144.62 (13)	C13—C14—C15—C16	178.95 (15)
C5—N2—C3—C4	−31.7 (2)	C19—C14—C15—C16	−1.7 (2)
N2—N3—C1—O1	−173.21 (14)	C13—C14—C19—C18	−179.55 (14)
N2—N3—C1—C2	4.81 (16)	C13—C14—C19—C20	−0.7 (2)
C6—N3—C1—O1	−17.8 (2)	C15—C14—C19—C18	1.1 (2)
C6—N3—C1—C2	160.23 (13)	C15—C14—C19—C20	179.89 (15)
N2—N3—C6—C7	36.9 (2)	C14—C15—C16—C17	1.3 (2)
N2—N3—C6—C11	−143.11 (14)	C15—C16—C17—C18	−0.3 (3)
C1—N3—C6—C7	−116.22 (17)	C16—C17—C18—C19	−0.4 (3)
C1—N3—C6—C11	63.7 (2)	C17—C18—C19—C14	−0.1 (2)
O1—C1—C2—N1	−0.5 (3)	C17—C18—C19—C20	−178.87 (16)
O1—C1—C2—C3	177.30 (16)	C14—C19—C20—C21	−0.8 (2)
N3—C1—C2—N1	−178.28 (15)	C18—C19—C20—C21	177.99 (15)
N3—C1—C2—C3	−0.50 (16)	C19—C20—C21—C22	−177.33 (15)
N1—C2—C3—N2	173.80 (13)	C19—C20—C21—C26	0.6 (2)
N1—C2—C3—C4	−10.1 (2)	C20—C21—C22—C23	175.93 (18)
C1—C2—C3—N2	−4.15 (16)	C26—C21—C22—C23	−2.0 (3)
C1—C2—C3—C4	171.95 (14)	C20—C21—C26—C13	1.2 (2)
N3—C6—C7—C8	−179.94 (16)	C20—C21—C26—C25	−174.80 (15)
C11—C6—C7—C8	0.1 (2)	C22—C21—C26—C13	179.17 (15)
N3—C6—C11—C10	−179.52 (15)	C22—C21—C26—C25	3.2 (2)
C7—C6—C11—C10	0.4 (2)	C21—C22—C23—C24	−0.6 (3)
C6—C7—C8—C9	−0.6 (3)	C22—C23—C24—C25	1.9 (3)
C7—C8—C9—C10	0.6 (3)	C23—C24—C25—C26	−0.6 (3)
C8—C9—C10—C11	0.0 (3)	C24—C25—C26—C13	−177.82 (17)
C9—C10—C11—C6	−0.5 (3)	C24—C25—C26—C21	−1.9 (2)
N1—C12—C13—C14	−45.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5a···O1i	0.96	2.59	3.530 (2)	167
C5—H5c···O1ii	0.96	2.57	3.5305 (19)	177
C12—H12···O1	0.93	2.37	3.0375 (19)	128
C15—H15···N1	0.93	2.42	3.024 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5a⋯O1i	0.96	2.59	3.530 (2)	167
C5—H5c⋯O1ii	0.96	2.57	3.5305 (19)	177
C12—H12⋯O1	0.93	2.37	3.0375 (19)	128
C15—H15⋯N1	0.93	2.42	3.024 (2)	123

Symmetry codes: (i) ; (ii) .