1-[5-(Anthracen-9-yl)-3-(4-nitro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one

Dong, B.-L.; Wang, M.-L.; Li, Y.-H.

doi:10.1107/S1600536810053365

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o386

doi:10.1107/S1600536810053365

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1-[5-(Anthracen-9-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one

Bao-Li Dong,^a Ming-Liang Wang ^a ^* and Yong-Hua Li ^a

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: wangmlchem@263.net

(Received 29 October 2010; accepted 20 December 2010; online 15 January 2011)

In the title compound, C₂₅H₁₉N₃O₃, steric repulsion between the methine H atom and one of the anthryl H atoms seems to be concomitant with the considerable distortion of the anthryl fragment from planarity. The side rings of the anthryl subtend an angle of 9.57 (8)°, which is an extreme value among the known reliably determined structures. This angle correlates with the length of the bond by which the anthryl is attached to the rest of the molecule. In the anthryl fragment, the maximum deviation of one of the C atoms from the mean plane is 0.126 (3) Å and regards the carrier C atom involved in the repulsion between the anthryl and the methine H atoms. The interplanar angle between the pyrazoline ring and the anthryl fragment is 88.36 (5)° and that between the pyrazoline and 4-nitrophenyl rings is 8.80 (15)°. Weak intermolecular C—H⋯N, C—H⋯π and π–π interactions [centroid–centroid distances of 3.7659 (17), 3.9477 (15) and 3.8972 (15) Å] are pesent in the structure.

Related literature

For the related structure 1′,2′,3′,4′-tetrahydro-1,3-diphenyl-4-p-tolylspiro[2-pyrazoline-5,2′-naphthalen]-1′-one, see: Krishna et al. (1999 ). For examples of the synthetic utility applied in the case of the title compound, see: Akama et al. (1996 ); Fahrni et al. (2003 ); Wei et al. (2007 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₂₅H₁₉N₃O₃
M_r = 409.43
Orthorhombic, P c a 2₁
a = 22.888 (5) Å
b = 9.4031 (19) Å
c = 8.9688 (18) Å
V = 1930.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.962, T_max = 0.982
19272 measured reflections
2352 independent reflections
2131 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.07
2352 reflections
288 parameters
69 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1,N2,C15–C17, C5–C7,C12–C14 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯N1	0.93	2.47	3.047 (3)	120
C8—H8A⋯N2	0.93	2.54	3.391 (3)	152
C8—H8A⋯Cg1	0.93	2.29	2.979 (3)	142
C15—H15A⋯Cg2ⁱ	0.99	2.90 (3)	3.731 (3)	142
C4—H4A⋯Cg3ⁱ	0.976	2.95	3.824 (3)	150
Symmetry code: (i) $[-x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053365/fb2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053365/fb2230Isup2.hkl

checkCIF report

Comment top

Pyrazoline derivatives are widely studied compounds. Some of them are capable of prototropic tautomerism (Akama et al., 1996). Others show elevated fluorescence. Therefore they have been widely used as fluorescence probes in some elaborated chemosensors (Fahrni et al., 2003) as well as hole-transport materials in electrophotography and electroluminescence (Wei et al., 2007). Here we report the structure of the title compound, a new derivative of pyrazoline.

In the pyrazoline ring, all the atoms are coplanar with the maximum deviation of 0.0258 (14)° for atom N1. The bond length of N2═C17 [1.2865 (31) Å] agrees with normal C═N bond (1.28 Å). The bond distance of N1—N2 [1.3796 (25) Å] conforms to the expected value (Krishna et al., 1999), too. The mean plane of pyrazoline ring makes interplanar angles of 8.80 (15)° and 88.36 (5)° with 4-nitrophenyl ring and the anthryl fragment, respectively.

The most interesting feature of the title structure is the distortion of the anthryl from planarity. The side rings of the anthryl fragment, i. e. the benzene rings C1\C2\C3\C4\C5\C14 and C7\C8\C9\C10\C11\C12, contain the angle 9.57 (8)°. In the anthryl fragment, the maximum deviation is 0.126 (3) Å from C4 atom to the mean plane of the ring. It can be related to the repulsion between the methine H15A and the anthryl H4A atoms (Fig. 1). The non-bonding distance between these two hydrogens equals to 1.95 Å. The attached atom H4A is also situated out of the plane of the ring.

Fig. 2 was obtained from the search on the Cambridge Crystallographic Structure Database (Allen, 2002; version CSD 5.31 with the last upgrade from Sept. 1 2010) carried out on the structures with R-factor < 0.05, with no disorder, no errors, with exclusion of the powder diffraction determinations and the polymeric structures or structures containing ions. This plot shows the correlation of the interplanar angle of the side anthryl rings with the C—C distance corresponding to C15—C6 (1.520 Å) in the title structure. It can be seen that the loss of planarity of the anthryl fragment is correlated to the lengthening of the bond by which is the anthryl attached to the the rest of the molecule. The present structure is situated at the extreme of the plot in Fig. 2.

There are present only weak intermolecular interactions in the structure: C—H···N, C—H···π- electron ring interactions (Tab. 1). Moreover, there are also π-electron ring -π-electron ring interactions present in the structure: Between the pyrazoline ring N1\N2\C17\C16\C15 and the benzene C1\C2\C3\C4\C5\C14 ring [symmetry code: -x,1-y,1/2+z] with the centroid-centroid distance equal to 3.7659 (17) Å; between the pyrazoline ring N1\N2\C17\C16\C15 and the benzene C5\C6\C7\C12\C13\C14 ring [symmetry code: x, y, z] with the centroid-centroid distance equal to 3.9477 (15) Å and between the pyrazoline ring N1\N2\C17\C16\C15 and the benzene C5\C6\C7\C12\C13\C14 ring [symmetry code: -x, 1-y, 1/2+z] with the centroid-centroid distance equal to 3.8972 (15) Å.

Related literature top

For the crystal structure of the related compound 1',2',3',4'-tetrahydro-1,3-diphenyl-4-p-tolylspiro[2-pyrazoline-5,2'-naphthalen]-1'-one, see: Krishna et al. (1999). For examples of the synthetic utility applied in the case of the title compound, see: Akama et al. (1996); Fahrni et al. (2003); Wei et al. (2007). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

3-(9-anthryl)-1-(4-nitrophenylprop)-2-en-1-one (3 mmol) and 0.6 g of hydrazine hydrate aqueous solution (1:1 w/w) were dissolved in 10 ml of glacial acetic acid. The mixture was stirred for 8 h at 391 K to give an orange solid. The product was then isolated and recrystallized from acetonitrile. The average size of light yellow single-crystals of the title structure equalled to 2.0 mm×1.0 mm×1.0 mm.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The title molecule, showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Fig. 2. The correlation between the interplanar angles of the side rings in the anthryl fragments retrieved from the Cambridge Crystallographic Database (Allen, 2002; version CSD 5.31 with the last upgrade from Sept. 1 2010) and the length of the bond by which the anthryl is attached to the rest of the molecule. (C_attached and C_anthryl correspond to C15 and C6 atoms of the title molecule, respectively.) The title compound is indicated by a red large circle while the rest of the compounds by small black squares.

1-[5-(Anthracen-9-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol- 1-yl]ethan-1-one top

Crystal data top

C₂₅H₁₉N₃O₃	F(000) = 856
M_r = 409.43	D_x = 1.409 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3824 reflections
a = 22.888 (5) Å	θ = 2.6–25.0°
b = 9.4031 (19) Å	µ = 0.09 mm⁻¹
c = 8.9688 (18) Å	T = 293 K
V = 1930.3 (7) Å³	Prism, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2352 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −29→29
T_min = 0.962, T_max = 0.982	k = −12→12
19272 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0488P)² + 0.2241P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2352 reflections	Δρ_max = 0.17 e Å⁻³
288 parameters	Δρ_min = −0.18 e Å⁻³
69 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: 0.018 (2)

Crystal data top

C₂₅H₁₉N₃O₃	V = 1930.3 (7) Å³
M_r = 409.43	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 22.888 (5) Å	µ = 0.09 mm⁻¹
b = 9.4031 (19) Å	T = 293 K
c = 8.9688 (18) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2352 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2131 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.982	R_int = 0.062
19272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	69 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.17 e Å⁻³
2352 reflections	Δρ_min = −0.18 e Å⁻³
288 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
N1	0.09343 (7)	0.5404 (2)	0.2678 (2)	0.0364 (4)
C5	−0.06548 (9)	0.5860 (2)	0.2243 (2)	0.0319 (5)
C6	−0.00794 (9)	0.6399 (2)	0.2175 (2)	0.0316 (4)
N2	0.14083 (8)	0.6030 (2)	0.3366 (2)	0.0360 (4)
C13	−0.09433 (10)	0.7481 (2)	0.0248 (3)	0.0410 (5)
H13A	−0.1228	0.7832	−0.0394	0.049*
C8	0.06219 (10)	0.8147 (2)	0.1055 (3)	0.0390 (5)
H8A	0.0915	0.7868	0.1711	0.047*
C17	0.12204 (9)	0.6934 (2)	0.4330 (3)	0.0335 (5)
C15	0.03652 (9)	0.5881 (2)	0.3311 (3)	0.0337 (5)
H15A	0.0208 (10)	0.506 (3)	0.387 (3)	0.040*
C7	0.00641 (9)	0.7476 (2)	0.1140 (2)	0.0326 (5)
C25	0.22213 (9)	0.7571 (3)	0.5197 (3)	0.0416 (5)
H25A	0.2374	0.6845	0.4611	0.050*
C12	−0.03748 (10)	0.7977 (2)	0.0123 (3)	0.0355 (5)
C23	0.23569 (10)	0.9475 (2)	0.6891 (3)	0.0405 (5)
C20	0.16176 (9)	0.7811 (2)	0.5216 (3)	0.0344 (5)
C1	−0.16961 (10)	0.6046 (3)	0.1484 (3)	0.0454 (6)
H1A	−0.1985	0.6480	0.0915	0.054*
O3	0.25365 (12)	1.1255 (2)	0.8605 (3)	0.0729 (7)
C14	−0.10970 (9)	0.6478 (2)	0.1304 (3)	0.0368 (5)
O1	0.05499 (8)	0.3576 (2)	0.1437 (3)	0.0563 (5)
C22	0.17679 (11)	0.9742 (3)	0.6936 (3)	0.0453 (6)
H22A	0.1620	1.0473	0.7523	0.054*
C4	−0.08379 (10)	0.4732 (3)	0.3199 (3)	0.0400 (5)
H4A	−0.0558 (12)	0.417 (3)	0.377 (3)	0.048*
C9	0.07371 (11)	0.9182 (3)	0.0041 (3)	0.0467 (6)
H9A	0.1101	0.9621	0.0041	0.056*
C21	0.13977 (10)	0.8900 (3)	0.6090 (3)	0.0421 (6)
H21A	0.0997	0.9068	0.6110	0.051*
C16	0.05649 (9)	0.7025 (3)	0.4436 (3)	0.0371 (5)
H16A	0.0425	0.7960	0.4152	0.045*
H16B	0.0430	0.6808	0.5435	0.045*
C3	−0.14067 (10)	0.4332 (3)	0.3298 (3)	0.0463 (6)
H3A	−0.1510	0.3589	0.3929	0.056*
C11	−0.02261 (12)	0.9016 (3)	−0.0966 (3)	0.0474 (6)
H11A	−0.0506	0.9297	−0.1659	0.057*
N3	0.27495 (10)	1.0378 (2)	0.7773 (3)	0.0515 (6)
C24	0.25901 (10)	0.8402 (3)	0.6037 (3)	0.0449 (6)
H24A	0.2991	0.8241	0.6027	0.054*
O2	0.32753 (9)	1.0208 (2)	0.7630 (3)	0.0698 (7)
C18	0.09882 (10)	0.4194 (2)	0.1846 (3)	0.0397 (5)
C2	−0.18442 (10)	0.5023 (3)	0.2462 (4)	0.0497 (6)
H29A	−0.2234	0.4772	0.2587	0.060*
C19	0.15940 (11)	0.3706 (3)	0.1485 (4)	0.0528 (7)
H19A	0.1576	0.2937	0.0783	0.079*
H19B	0.1784	0.3389	0.2380	0.079*
H19C	0.1811	0.4480	0.1061	0.079*
C10	0.03117 (11)	0.9604 (3)	−0.1016 (3)	0.0515 (7)
H10A	0.0402	1.0280	−0.1737	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0253 (8)	0.0385 (10)	0.0455 (11)	0.0019 (7)	−0.0063 (8)	0.0004 (9)
C5	0.0279 (10)	0.0329 (10)	0.0349 (12)	0.0039 (8)	−0.0028 (9)	−0.0064 (9)
C6	0.0271 (9)	0.0328 (10)	0.0348 (11)	0.0048 (8)	−0.0054 (9)	−0.0017 (9)
N2	0.0266 (9)	0.0383 (10)	0.0430 (10)	−0.0011 (7)	−0.0073 (8)	0.0041 (9)
C13	0.0389 (12)	0.0428 (12)	0.0412 (13)	0.0136 (10)	−0.0119 (11)	−0.0007 (11)
C8	0.0350 (11)	0.0412 (11)	0.0408 (13)	0.0055 (9)	0.0004 (10)	0.0055 (10)
C17	0.0275 (10)	0.0370 (11)	0.0361 (12)	0.0006 (8)	−0.0023 (9)	0.0063 (10)
C15	0.0259 (10)	0.0389 (11)	0.0362 (11)	−0.0015 (9)	−0.0042 (9)	0.0071 (10)
C7	0.0335 (11)	0.0330 (10)	0.0312 (11)	0.0063 (8)	−0.0004 (9)	−0.0024 (9)
C25	0.0313 (11)	0.0448 (13)	0.0486 (14)	0.0004 (9)	−0.0041 (11)	−0.0027 (12)
C12	0.0376 (11)	0.0352 (10)	0.0336 (11)	0.0087 (9)	−0.0035 (10)	−0.0003 (10)
C23	0.0437 (13)	0.0394 (11)	0.0382 (13)	−0.0085 (10)	−0.0099 (11)	0.0081 (10)
C20	0.0305 (10)	0.0387 (11)	0.0340 (11)	−0.0038 (8)	−0.0028 (9)	0.0065 (10)
C1	0.0283 (11)	0.0526 (14)	0.0553 (15)	0.0067 (10)	−0.0114 (11)	−0.0095 (13)
O3	0.0843 (15)	0.0646 (12)	0.0698 (16)	−0.0126 (13)	−0.0163 (12)	−0.0162 (13)
C14	0.0304 (10)	0.0378 (11)	0.0421 (12)	0.0058 (9)	−0.0055 (10)	−0.0091 (10)
O1	0.0478 (10)	0.0497 (10)	0.0713 (13)	−0.0029 (8)	−0.0149 (10)	−0.0094 (10)
C22	0.0483 (14)	0.0478 (13)	0.0399 (13)	0.0014 (11)	−0.0015 (11)	−0.0043 (11)
C4	0.0316 (12)	0.0417 (13)	0.0468 (14)	−0.0006 (9)	−0.0033 (10)	0.0026 (11)
C9	0.0414 (13)	0.0461 (13)	0.0527 (15)	0.0033 (10)	0.0076 (12)	0.0102 (12)
C21	0.0316 (11)	0.0502 (13)	0.0445 (14)	0.0019 (10)	−0.0047 (10)	−0.0013 (11)
C16	0.0287 (10)	0.0493 (13)	0.0333 (12)	0.0008 (9)	−0.0025 (9)	0.0014 (10)
C3	0.0358 (12)	0.0499 (14)	0.0531 (15)	−0.0074 (10)	0.0019 (11)	−0.0012 (12)
C11	0.0510 (14)	0.0498 (13)	0.0413 (13)	0.0145 (11)	−0.0051 (12)	0.0072 (11)
N3	0.0599 (14)	0.0461 (12)	0.0487 (13)	−0.0135 (10)	−0.0163 (12)	0.0074 (11)
C24	0.0304 (11)	0.0498 (13)	0.0546 (16)	−0.0033 (10)	−0.0073 (11)	0.0050 (12)
O2	0.0491 (11)	0.0722 (13)	0.0881 (17)	−0.0182 (10)	−0.0255 (12)	−0.0016 (13)
C18	0.0392 (12)	0.0353 (11)	0.0446 (13)	0.0029 (9)	−0.0087 (10)	0.0026 (11)
C2	0.0269 (10)	0.0579 (15)	0.0642 (17)	−0.0043 (10)	−0.0019 (12)	−0.0107 (14)
C19	0.0482 (14)	0.0493 (14)	0.0609 (17)	0.0122 (11)	−0.0046 (13)	−0.0073 (14)
C10	0.0572 (16)	0.0498 (14)	0.0476 (15)	0.0119 (12)	0.0084 (13)	0.0191 (12)

Geometric parameters (Å, º) top

N1—C18	1.367 (3)	C20—C21	1.384 (3)
N1—N2	1.380 (3)	C1—C2	1.345 (4)
N1—C15	1.490 (3)	C1—C14	1.439 (3)
C5—C6	1.412 (3)	C1—H1A	0.9300
C5—C4	1.427 (3)	O3—N3	1.214 (3)
C5—C14	1.440 (3)	O1—C18	1.216 (3)
C6—C7	1.413 (3)	C22—C21	1.386 (3)
C6—C15	1.520 (3)	C22—H22A	0.9300
N2—C17	1.287 (3)	C4—C3	1.358 (3)
C13—C14	1.382 (4)	C4—H4A	0.97 (3)
C13—C12	1.387 (3)	C9—C10	1.416 (4)
C13—H13A	0.9300	C9—H9A	0.9300
C8—C9	1.358 (3)	C21—H21A	0.9300
C8—C7	1.426 (3)	C16—H16A	0.9700
C8—H8A	0.9300	C16—H16B	0.9700
C17—C20	1.462 (3)	C3—C2	1.409 (4)
C17—C16	1.506 (3)	C3—H3A	0.9300
C15—C16	1.544 (3)	C11—C10	1.350 (4)
C15—H15A	0.99 (3)	C11—H11A	0.9300
C7—C12	1.436 (3)	N3—O2	1.221 (3)
C25—C24	1.375 (3)	C24—H24A	0.9300
C25—C20	1.400 (3)	C18—C19	1.496 (3)
C25—H25A	0.9300	C2—H29A	0.9300
C12—C11	1.423 (4)	C19—H19A	0.9600
C23—C22	1.372 (3)	C19—H19B	0.9600
C23—C24	1.374 (4)	C19—H19C	0.9600
C23—N3	1.468 (3)	C10—H10A	0.9300

C18—N1—N2	121.89 (18)	C23—C22—C21	118.7 (2)
C18—N1—C15	122.51 (18)	C23—C22—H22A	120.6
N2—N1—C15	112.89 (18)	C21—C22—H22A	120.6
C6—C5—C4	124.50 (19)	C3—C4—C5	121.8 (2)
C6—C5—C14	119.1 (2)	C3—C4—H4A	116.5 (16)
C4—C5—C14	116.45 (19)	C5—C4—H4A	121.6 (16)
C5—C6—C7	120.14 (18)	C8—C9—C10	121.0 (2)
C5—C6—C15	118.71 (19)	C8—C9—H9A	119.5
C7—C6—C15	120.98 (18)	C10—C9—H9A	119.5
C17—N2—N1	108.61 (17)	C20—C21—C22	120.7 (2)
C14—C13—C12	121.6 (2)	C20—C21—H21A	119.7
C14—C13—H13A	119.2	C22—C21—H21A	119.7
C12—C13—H13A	119.2	C17—C16—C15	102.38 (18)
C9—C8—C7	121.8 (2)	C17—C16—H16A	111.3
C9—C8—H8A	119.1	C15—C16—H16A	111.3
C7—C8—H8A	119.1	C17—C16—H16B	111.3
N2—C17—C20	122.01 (19)	C15—C16—H16B	111.3
N2—C17—C16	114.39 (19)	H16A—C16—H16B	109.2
C20—C17—C16	123.6 (2)	C4—C3—C2	121.3 (3)
N1—C15—C6	115.24 (19)	C4—C3—H3A	119.4
N1—C15—C16	101.51 (16)	C2—C3—H3A	119.4
C6—C15—C16	114.36 (18)	C10—C11—C12	121.4 (2)
N1—C15—H15A	106.1 (14)	C10—C11—H11A	119.3
C6—C15—H15A	110.3 (15)	C12—C11—H11A	119.3
C16—C15—H15A	108.6 (16)	O3—N3—O2	123.3 (2)
C6—C7—C8	124.09 (19)	O3—N3—C23	118.6 (2)
C6—C7—C12	119.35 (19)	O2—N3—C23	118.1 (2)
C8—C7—C12	116.5 (2)	C23—C24—C25	118.9 (2)
C24—C25—C20	120.5 (2)	C23—C24—H24A	120.5
C24—C25—H25A	119.7	C25—C24—H24A	120.5
C20—C25—H25A	119.7	O1—C18—N1	119.2 (2)
C13—C12—C11	120.7 (2)	O1—C18—C19	123.6 (2)
C13—C12—C7	119.6 (2)	N1—C18—C19	117.2 (2)
C11—C12—C7	119.6 (2)	C1—C2—C3	119.8 (2)
C22—C23—C24	122.2 (2)	C1—C2—H29A	120.1
C22—C23—N3	118.7 (2)	C3—C2—H29A	120.1
C24—C23—N3	119.2 (2)	C18—C19—H19A	109.5
C21—C20—C25	119.0 (2)	C18—C19—H19B	109.5
C21—C20—C17	119.93 (19)	H19A—C19—H19B	109.5
C25—C20—C17	121.1 (2)	C18—C19—H19C	109.5
C2—C1—C14	121.0 (2)	H19A—C19—H19C	109.5
C2—C1—H1A	119.5	H19B—C19—H19C	109.5
C14—C1—H1A	119.5	C11—C10—C9	119.4 (2)
C13—C14—C1	120.8 (2)	C11—C10—H10A	120.3
C13—C14—C5	119.8 (2)	C9—C10—H10A	120.3
C1—C14—C5	119.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1,N2,C15–C17, C5–C7,C12–C14 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1	0.93	2.47	3.047 (3)	120
C8—H8A···N2	0.93	2.54	3.391 (3)	152
C8—H8A···Cg1	0.93	2.29	2.979 (3)	142
C15—H15A···Cg2ⁱ	0.99	2.90 (3)	3.731 (3)	142
C4—H4A···Cg3ⁱ	0.976	2.95	3.824 (3)	150

Symmetry code: (i) −x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉N₃O₃
M_r	409.43
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	22.888 (5), 9.4031 (19), 8.9688 (18)
V (Å³)	1930.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.962, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	19272, 2352, 2131
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.07
No. of reflections	2352
No. of parameters	288
No. of restraints	69
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1,N2,C15–C17, C5–C7,C12–C14 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1	0.93	2.47	3.047 (3)	120.0
C8—H8A···N2	0.93	2.54	3.391 (3)	151.8
C8—H8A···Cg1	0.93	2.29	2.979 (3)	142
C15—H15A···Cg2ⁱ	0.99	2.90 (3)	3.731 (3)	142
C4—H4A···Cg3ⁱ	0.976	2.95	3.824 (3)	150

Symmetry code: (i) −x, −y+1, z+1/2.

References

Akama, Y. & Tong, A. (1996). Microchem. J. 53, 34–41. CrossRef CAS Web of Science Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fahrni, C. J., Yang, L. C. & VanDerveer, D. G. (2003). J. Am. Chem. Soc. 125, 3799–3812. Web of Science CSD CrossRef PubMed CAS Google Scholar
Krishna, R., Velmurugan, D., Murugesan, R., Shanmuga Sundaram, M. & Raghunathan, R. (1999). Acta Cryst. C55, 1676–1677. CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, X., Yang, G., Cheng, J., Lu, Z. & Xie, M. (2007). Opt. Mater. 29, 936–940. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 2| February 2011| Page o386

doi:10.1107/S1600536810053365

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

1-[5-(Anthracen-9-yl)-3-(4-nitro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]ethan-1-one

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Experimental

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organic compounds

1-[5-(Anthracen-9-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one