1-[5-(Anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(25)H(20)N(2)O, the pyrazoline ring is nearly planar [maximum atomic deviation = 0.0254 (17) Å]; but the anthracene ring system is distorted from a coplanar structure [maximum atomic deviation = 0.181 (3) Å], the dihedral angle between the outer benzene rings being 10.68 (13)°. The pyrazoline ring is almost perpendicular to the mean plane of the anthracene ring system [dihedral angle = 76.94 (8)°], but nearly coplanar with the phenyl ring [dihedral angle = 1.63 (7)°]. π-π stacking is observed between parallel benzene rings of adjacent anthracene units, the face-to-face distance being 3.27 (3) Å. Weak intra-molecular C-H⋯N hydrogen bonding also occurs.

Related literature

For applications of pyrazoline derivatives, see: Christoph et al. (2003 ▶); Parmar et al. (1974 ▶); Soni et al. (1978 ▶); Wei et al. (2007 ▶). For a related structure, see: Krishna et al. (1999 ▶).

Experimental

Crystal data

C25H20N2O

M = 364.43

Monoclinic,

a = 8.7102 (17) Å

b = 16.251 (3) Å

c = 13.309 (3) Å

β = 91.49 (3)°

V = 1883.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.24 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

16656 measured reflections

3538 independent reflections

2021 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.142

S = 1.04

3538 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005018X/xu5095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005018X/xu5095Isup2.hkl

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

C25H20N2O	F(000) = 768
Mr = 364.43	Dx = 1.285 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3850 reflections
a = 8.7102 (17) Å	θ = 2.6–25.0°
b = 16.251 (3) Å	µ = 0.08 mm−1
c = 13.309 (3) Å	T = 293 K
β = 91.49 (3)°	Block, yellow
V = 1883.2 (7) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2021 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.090
graphite	θmax = 25.6°, θmin = 3.0°
Detector resolution: 13.6 pixels mm-1	h = −10→10
φ and ω scans	k = −19→19
16656 measured reflections	l = −16→16
3538 independent reflections

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.2473P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3538 reflections	Δρmax = 0.14 e Å−3
255 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0174 (17)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.4492 (2)	0.69151 (12)	0.36622 (16)	0.0460 (6)
N2	0.4001 (2)	0.61021 (12)	0.36062 (16)	0.0462 (6)
O1	0.5886 (2)	0.79431 (13)	0.30449 (17)	0.0783 (7)
C1	0.1365 (3)	0.76484 (17)	0.35515 (19)	0.0487 (7)
H1A	0.1765	0.7119	0.3520	0.058*
C2	0.0037 (3)	0.78223 (18)	0.30343 (19)	0.0529 (7)
H2B	−0.0474	0.7406	0.2682	0.063*
C3	−0.0573 (3)	0.86234 (18)	0.3024 (2)	0.0527 (7)
H3A	−0.1465	0.8740	0.2653	0.063*
C4	0.0144 (3)	0.92193 (17)	0.35558 (19)	0.0504 (7)
H4A	−0.0245	0.9752	0.3528	0.061*
C5	0.1481 (3)	0.90571 (15)	0.41604 (19)	0.0430 (7)
C6	0.2101 (3)	0.96556 (16)	0.47959 (19)	0.0463 (7)
H6A	0.1674	1.0180	0.4788	0.056*
C7	0.3337 (3)	0.94940 (15)	0.54413 (19)	0.0441 (7)
C8	0.3868 (3)	1.00942 (16)	0.6146 (2)	0.0521 (7)
H8A	0.3380	1.0603	0.6168	0.063*
C9	0.5058 (4)	0.99439 (18)	0.6782 (2)	0.0581 (8)
H9A	0.5372	1.0339	0.7249	0.070*
C10	0.5831 (3)	0.91788 (18)	0.67331 (19)	0.0579 (8)
H10A	0.6663	0.9076	0.7167	0.069*
C11	0.5375 (3)	0.85926 (17)	0.60629 (19)	0.0521 (7)
H11A	0.5917	0.8100	0.6041	0.063*
C12	0.4088 (3)	0.87087 (15)	0.53899 (18)	0.0402 (6)
C13	0.3515 (3)	0.81000 (15)	0.47169 (18)	0.0416 (6)
C14	0.2165 (3)	0.82539 (15)	0.41421 (18)	0.0404 (6)
C15	0.4337 (3)	0.72775 (15)	0.46727 (19)	0.0485 (7)
H15A	0.5368	0.7347	0.4972	0.058*
C16	0.3539 (3)	0.65722 (15)	0.52291 (19)	0.0553 (8)
H16A	0.4134	0.6405	0.5821	0.066*
H16B	0.2518	0.6733	0.5429	0.066*
C17	0.3464 (3)	0.58952 (15)	0.4462 (2)	0.0447 (7)
C18	0.5338 (3)	0.72582 (18)	0.2927 (2)	0.0547 (8)
C19	0.5526 (4)	0.67627 (19)	0.1987 (2)	0.0841 (11)
H19A	0.5996	0.7097	0.1486	0.126*
H19B	0.4538	0.6580	0.1742	0.126*
H19C	0.6166	0.6294	0.2132	0.126*
C20	0.2820 (3)	0.50776 (15)	0.4632 (2)	0.0456 (7)
C21	0.2784 (3)	0.44894 (17)	0.3877 (2)	0.0548 (8)
H21A	0.3193	0.4612	0.3256	0.066*
C22	0.2152 (3)	0.37274 (17)	0.4034 (2)	0.0654 (9)
H22A	0.2129	0.3343	0.3517	0.078*
C23	0.1557 (4)	0.3528 (2)	0.4944 (3)	0.0726 (10)
H23A	0.1140	0.3010	0.5048	0.087*
C24	0.1582 (4)	0.4102 (2)	0.5699 (3)	0.0811 (10)
H24A	0.1183	0.3971	0.6321	0.097*
C25	0.2195 (4)	0.48683 (19)	0.5542 (2)	0.0690 (9)
H25A	0.2190	0.5254	0.6057	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.0528 (14)	0.0359 (13)	0.0500 (14)	−0.0003 (10)	0.0125 (11)	−0.0049 (10)
N2	0.0511 (14)	0.0351 (14)	0.0529 (15)	−0.0004 (10)	0.0099 (11)	−0.0014 (10)
O1	0.0781 (16)	0.0536 (14)	0.1048 (18)	−0.0203 (11)	0.0346 (13)	−0.0108 (12)
C1	0.0473 (18)	0.0493 (17)	0.0500 (17)	−0.0010 (13)	0.0088 (14)	−0.0074 (13)
C2	0.0492 (18)	0.064 (2)	0.0454 (17)	−0.0042 (14)	0.0061 (14)	−0.0068 (14)
C3	0.0457 (18)	0.065 (2)	0.0478 (17)	0.0071 (15)	0.0057 (13)	−0.0004 (14)
C4	0.0485 (18)	0.0535 (19)	0.0497 (17)	0.0095 (14)	0.0098 (14)	0.0053 (14)
C5	0.0421 (17)	0.0445 (17)	0.0430 (15)	0.0008 (12)	0.0136 (12)	0.0029 (12)
C6	0.0496 (18)	0.0370 (16)	0.0531 (18)	0.0044 (12)	0.0148 (14)	0.0007 (13)
C7	0.0500 (18)	0.0393 (16)	0.0438 (16)	−0.0041 (12)	0.0178 (13)	−0.0030 (12)
C8	0.059 (2)	0.0425 (17)	0.0554 (18)	−0.0078 (13)	0.0183 (16)	−0.0112 (13)
C9	0.073 (2)	0.055 (2)	0.0469 (18)	−0.0178 (16)	0.0110 (16)	−0.0100 (14)
C10	0.070 (2)	0.059 (2)	0.0444 (17)	−0.0115 (16)	−0.0028 (14)	0.0003 (14)
C11	0.061 (2)	0.0496 (18)	0.0457 (17)	−0.0015 (14)	0.0003 (14)	0.0004 (13)
C12	0.0431 (16)	0.0384 (16)	0.0394 (15)	−0.0048 (12)	0.0087 (12)	0.0042 (11)
C13	0.0469 (17)	0.0353 (15)	0.0433 (15)	−0.0005 (12)	0.0114 (13)	−0.0006 (11)
C14	0.0406 (16)	0.0378 (16)	0.0430 (15)	0.0002 (11)	0.0091 (12)	−0.0017 (11)
C15	0.0525 (17)	0.0430 (17)	0.0499 (17)	0.0043 (13)	−0.0007 (13)	−0.0057 (13)
C16	0.080 (2)	0.0434 (17)	0.0427 (16)	0.0065 (14)	0.0023 (14)	0.0010 (13)
C17	0.0510 (17)	0.0388 (17)	0.0443 (17)	0.0086 (12)	0.0014 (13)	0.0009 (12)
C18	0.0534 (18)	0.0440 (19)	0.068 (2)	−0.0033 (14)	0.0189 (15)	−0.0008 (15)
C19	0.112 (3)	0.068 (2)	0.075 (2)	−0.0151 (19)	0.053 (2)	−0.0067 (18)
C20	0.0470 (17)	0.0408 (17)	0.0494 (17)	0.0076 (12)	0.0051 (13)	0.0030 (13)
C21	0.0619 (19)	0.0480 (19)	0.0550 (19)	0.0023 (14)	0.0136 (14)	0.0019 (14)
C22	0.082 (2)	0.0430 (19)	0.072 (2)	−0.0049 (16)	0.0147 (17)	−0.0024 (15)
C23	0.080 (2)	0.053 (2)	0.086 (3)	−0.0091 (17)	0.0176 (19)	0.0107 (19)
C24	0.109 (3)	0.063 (2)	0.073 (2)	−0.009 (2)	0.032 (2)	0.0091 (19)
C25	0.098 (3)	0.055 (2)	0.055 (2)	−0.0081 (17)	0.0166 (17)	0.0012 (15)

N1—C18	1.360 (3)	C11—C12	1.430 (3)
N1—N2	1.390 (3)	C11—H11A	0.9300
N1—C15	1.478 (3)	C12—C13	1.416 (3)
N2—C17	1.287 (3)	C13—C14	1.408 (3)
O1—C18	1.220 (3)	C13—C15	1.518 (3)
C1—C2	1.360 (4)	C15—C16	1.540 (4)
C1—C14	1.429 (3)	C15—H15A	0.9800
C1—H1A	0.9300	C16—C17	1.501 (3)
C2—C3	1.406 (4)	C16—H16A	0.9700
C2—H2B	0.9300	C16—H16B	0.9700
C3—C4	1.343 (4)	C17—C20	1.462 (3)
C3—H3A	0.9300	C18—C19	1.500 (4)
C4—C5	1.423 (4)	C19—H19A	0.9600
C4—H4A	0.9300	C19—H19B	0.9600
C5—C6	1.389 (3)	C19—H19C	0.9600
C5—C14	1.435 (3)	C20—C25	1.383 (4)
C6—C7	1.385 (3)	C20—C21	1.387 (3)
C6—H6A	0.9300	C21—C22	1.373 (4)
C7—C8	1.423 (3)	C21—H21A	0.9300
C7—C12	1.436 (3)	C22—C23	1.368 (4)
C8—C9	1.343 (4)	C22—H22A	0.9300
C8—H8A	0.9300	C23—C24	1.371 (4)
C9—C10	1.416 (4)	C23—H23A	0.9300
C9—H9A	0.9300	C24—C25	1.374 (4)
C10—C11	1.357 (4)	C24—H24A	0.9300
C10—H10A	0.9300	C25—H25A	0.9300
C18—N1—N2	121.5 (2)	C13—C14—C5	119.6 (2)
C18—N1—C15	123.8 (2)	C1—C14—C5	116.0 (2)
N2—N1—C15	113.1 (2)	N1—C15—C13	116.1 (2)
C17—N2—N1	108.6 (2)	N1—C15—C16	101.2 (2)
C2—C1—C14	122.1 (3)	C13—C15—C16	114.7 (2)
C2—C1—H1A	118.9	N1—C15—H15A	108.1
C14—C1—H1A	118.9	C13—C15—H15A	108.1
C1—C2—C3	120.9 (3)	C16—C15—H15A	108.1
C1—C2—H2B	119.6	C17—C16—C15	103.3 (2)
C3—C2—H2B	119.6	C17—C16—H16A	111.1
C4—C3—C2	119.5 (3)	C15—C16—H16A	111.1
C4—C3—H3A	120.2	C17—C16—H16B	111.1
C2—C3—H3A	120.2	C15—C16—H16B	111.1
C3—C4—C5	121.8 (3)	H16A—C16—H16B	109.1
C3—C4—H4A	119.1	N2—C17—C20	121.6 (2)
C5—C4—H4A	119.1	N2—C17—C16	113.6 (2)
C6—C5—C4	121.0 (2)	C20—C17—C16	124.8 (2)
C6—C5—C14	119.5 (2)	O1—C18—N1	120.0 (3)
C4—C5—C14	119.5 (2)	O1—C18—C19	123.1 (3)
C7—C6—C5	121.9 (2)	N1—C18—C19	116.9 (2)
C7—C6—H6A	119.0	C18—C19—H19A	109.5
C5—C6—H6A	119.0	C18—C19—H19B	109.5
C6—C7—C8	120.9 (2)	H19A—C19—H19B	109.5
C6—C7—C12	119.1 (2)	C18—C19—H19C	109.5
C8—C7—C12	120.0 (3)	H19A—C19—H19C	109.5
C9—C8—C7	121.5 (3)	H19B—C19—H19C	109.5
C9—C8—H8A	119.2	C25—C20—C21	117.6 (3)
C7—C8—H8A	119.2	C25—C20—C17	121.3 (2)
C8—C9—C10	119.4 (3)	C21—C20—C17	121.1 (2)
C8—C9—H9A	120.3	C22—C21—C20	120.8 (3)
C10—C9—H9A	120.3	C22—C21—H21A	119.6
C11—C10—C9	121.0 (3)	C20—C21—H21A	119.6
C11—C10—H10A	119.5	C23—C22—C21	120.7 (3)
C9—C10—H10A	119.5	C23—C22—H22A	119.6
C10—C11—C12	122.0 (3)	C21—C22—H22A	119.6
C10—C11—H11A	119.0	C22—C23—C24	119.3 (3)
C12—C11—H11A	119.0	C22—C23—H23A	120.3
C13—C12—C11	124.2 (2)	C24—C23—H23A	120.3
C13—C12—C7	119.8 (2)	C23—C24—C25	120.2 (3)
C11—C12—C7	116.0 (2)	C23—C24—H24A	119.9
C14—C13—C12	119.7 (2)	C25—C24—H24A	119.9
C14—C13—C15	121.5 (2)	C24—C25—C20	121.3 (3)
C12—C13—C15	118.7 (2)	C24—C25—H25A	119.3
C13—C14—C1	124.4 (2)	C20—C25—H25A	119.3

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N2	0.93	2.55	3.404 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N2	0.93	2.55	3.404 (3)	152