4,6-Bis(4-fluoro-phen-yl)-2-phenyl-1H-indazol-3(2H)-one.

In the title compound, C(25)H(16)F(2)N(2)O, the pyrazole ring is almost planar (r.m.s. deviation = 0.028 Å) and makes a dihedral angle of 5.86 (11)° with the indazole benzene ring. The dihedral angle between the pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The dihedral angles between the unsubstituted phenyl and the two fluoro-phenyl groups are 57.69 (10) and 18.01 (10)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯F inter-actions, forming infinite chains along the b axis with graph-set motif R(3) (2)(19). The crystal structure is further consolidated by π-π stacking [centroid-centroid distances = 3.5916 (13) and 3.6890 (13) Å] and C-H⋯π inter-actions.

Related literature

For the pharmacological activity of indazole derivatives, see: Beylin et al. (1991 ▶); George et al. (1998 ▶); Jain et al. (1987 ▶); Palazzo et al. (1966 ▶); Popat et al. (2003 ▶); Roman (1990 ▶). For related structures, see: van der Helm et al. (1979 ▶); Fun et al. (2010 ▶). For hybridization and electron delocalization around N atoms, see: Susindran et al. (2010 ▶); Jin et al. (2004 ▶). For graph-set analysis, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H16F2N2O

M = 398.40

Orthorhombic,

a = 15.2947 (4) Å

b = 11.6259 (2) Å

c = 20.9388 (5) Å

V = 3723.23 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.49 × 0.38 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.895, T max = 0.977

19870 measured reflections

3827 independent reflections

3416 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.135

S = 1.09

3827 reflections

275 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016369/qk2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016369/qk2004Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016369/qk2004Isup3.cml

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

C25H16F2N2O	F(000) = 1648
Mr = 398.40	Dx = 1.421 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 11209 reflections
a = 15.2947 (4) Å	θ = 5.2–37.5°
b = 11.6259 (2) Å	µ = 0.10 mm−1
c = 20.9388 (5) Å	T = 123 K
V = 3723.23 (15) Å3	Prism, colourless
Z = 8	0.49 × 0.38 × 0.23 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3827 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3416 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.5081 pixels mm-1	θmax = 26.5°, θmin = 5.2°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −14→14
Tmin = 0.895, Tmax = 0.977	l = −26→26
19870 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0462P)2 + 4.0317P] where P = (Fo2 + 2Fc2)/3
3827 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.65 e Å−3
1 restraint	Δρmin = −0.35 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F1	0.60370 (13)	−0.57691 (11)	0.22016 (9)	0.0656 (6)
F2	0.48986 (10)	0.29173 (14)	0.53611 (7)	0.0525 (5)
O1	0.73203 (11)	−0.14990 (12)	0.11749 (7)	0.0351 (5)
N1	0.72290 (11)	0.04878 (13)	0.11220 (7)	0.0239 (5)
N2	0.68782 (11)	0.13815 (13)	0.14893 (8)	0.0241 (5)
C1	0.70924 (15)	−0.05733 (16)	0.14107 (9)	0.0269 (6)
C2	0.66455 (14)	−0.03003 (16)	0.20027 (9)	0.0272 (6)
C3	0.63295 (16)	−0.10034 (17)	0.25063 (10)	0.0323 (6)
C4	0.60213 (13)	−0.04532 (16)	0.30476 (9)	0.0246 (5)
C5	0.60116 (12)	0.07752 (16)	0.31012 (9)	0.0230 (5)
C6	0.62766 (13)	0.14448 (16)	0.25935 (9)	0.0248 (6)
C7	0.65858 (13)	0.08914 (16)	0.20431 (9)	0.0241 (5)
C8	0.62753 (14)	−0.22733 (16)	0.24316 (9)	0.0257 (6)
C9	0.58886 (14)	−0.27250 (18)	0.18834 (10)	0.0291 (6)
C10	0.57996 (15)	−0.3901 (2)	0.18045 (11)	0.0355 (7)
C11	0.61074 (16)	−0.46066 (17)	0.22766 (12)	0.0382 (7)
C12	0.64919 (16)	−0.42035 (19)	0.28203 (12)	0.0391 (7)
C13	0.65705 (15)	−0.30264 (18)	0.28970 (10)	0.0315 (6)
C14	0.57027 (12)	0.13239 (17)	0.37010 (9)	0.0246 (6)
C15	0.58997 (14)	0.08541 (18)	0.42973 (10)	0.0302 (6)
C16	0.56348 (15)	0.1384 (2)	0.48586 (10)	0.0365 (7)
C17	0.51680 (14)	0.2389 (2)	0.48129 (10)	0.0355 (7)
C18	0.49559 (14)	0.28874 (19)	0.42389 (11)	0.0338 (6)
C19	0.52226 (13)	0.23481 (18)	0.36821 (10)	0.0280 (6)
C20	0.74707 (13)	0.07083 (15)	0.04813 (9)	0.0216 (5)
C21	0.71378 (14)	0.16740 (16)	0.01763 (9)	0.0257 (6)
C22	0.73814 (15)	0.19020 (17)	−0.04494 (9)	0.0303 (6)
C23	0.79396 (15)	0.11777 (17)	−0.07719 (10)	0.0303 (6)
C24	0.82668 (15)	0.02163 (18)	−0.04644 (10)	0.0320 (6)
C25	0.80400 (13)	−0.00225 (17)	0.01629 (10)	0.0279 (6)
HN2	0.7174 (14)	0.2009 (14)	0.1477 (12)	0.038 (7)*
H4	0.58140	−0.08940	0.33860	0.0300*
H6	0.62510	0.22430	0.26150	0.0300*
H9	0.56880	−0.22300	0.15670	0.0350*
H10	0.55380	−0.42030	0.14400	0.0430*
H12	0.66960	−0.47070	0.31310	0.0470*
H13	0.68250	−0.27360	0.32670	0.0380*
H15	0.62150	0.01710	0.43190	0.0360*
H16	0.57700	0.10670	0.52540	0.0440*
H18	0.46410	0.35710	0.42240	0.0400*
H19	0.50800	0.26720	0.32890	0.0340*
H21	0.67550	0.21630	0.03890	0.0310*
H22	0.71650	0.25530	−0.06540	0.0360*
H23	0.80960	0.13330	−0.11920	0.0360*
H24	0.86430	−0.02760	−0.06810	0.0380*
H25	0.82670	−0.06660	0.03680	0.0330*

	U11	U22	U33	U12	U13	U23
F1	0.0954 (13)	0.0186 (7)	0.0829 (12)	−0.0145 (7)	0.0149 (10)	−0.0064 (7)
F2	0.0579 (9)	0.0652 (10)	0.0345 (7)	0.0125 (8)	0.0096 (7)	−0.0210 (7)
O1	0.0646 (11)	0.0155 (7)	0.0251 (7)	0.0055 (7)	0.0088 (7)	0.0007 (6)
N1	0.0364 (9)	0.0141 (7)	0.0213 (8)	0.0030 (7)	0.0009 (7)	−0.0001 (6)
N2	0.0366 (9)	0.0142 (7)	0.0216 (8)	0.0004 (7)	0.0023 (7)	−0.0007 (6)
C1	0.0440 (12)	0.0172 (9)	0.0195 (9)	0.0009 (8)	0.0002 (8)	0.0024 (7)
C2	0.0421 (11)	0.0179 (9)	0.0216 (9)	0.0008 (8)	0.0008 (8)	−0.0011 (7)
C3	0.0489 (13)	0.0216 (10)	0.0265 (10)	−0.0039 (9)	0.0052 (9)	0.0002 (8)
C4	0.0311 (10)	0.0216 (9)	0.0210 (9)	−0.0026 (8)	0.0005 (8)	0.0014 (7)
C5	0.0253 (9)	0.0225 (9)	0.0213 (9)	0.0023 (7)	−0.0030 (8)	−0.0027 (7)
C6	0.0344 (11)	0.0149 (8)	0.0250 (10)	0.0026 (7)	−0.0019 (8)	−0.0011 (7)
C7	0.0326 (10)	0.0177 (9)	0.0220 (9)	−0.0008 (8)	−0.0024 (8)	0.0011 (7)
C8	0.0365 (11)	0.0184 (9)	0.0222 (9)	−0.0025 (8)	0.0058 (8)	−0.0002 (7)
C9	0.0345 (11)	0.0292 (10)	0.0237 (10)	0.0015 (9)	0.0011 (9)	0.0034 (8)
C10	0.0384 (12)	0.0360 (12)	0.0321 (11)	−0.0130 (10)	0.0035 (9)	−0.0104 (9)
C11	0.0496 (14)	0.0153 (9)	0.0496 (14)	−0.0070 (9)	0.0130 (11)	−0.0019 (9)
C12	0.0503 (14)	0.0262 (11)	0.0407 (13)	0.0018 (10)	0.0019 (11)	0.0134 (10)
C13	0.0417 (12)	0.0291 (11)	0.0238 (10)	−0.0061 (9)	−0.0023 (9)	0.0046 (8)
C14	0.0247 (9)	0.0246 (10)	0.0244 (10)	−0.0009 (7)	−0.0005 (8)	−0.0038 (8)
C15	0.0351 (11)	0.0303 (10)	0.0253 (10)	0.0051 (9)	0.0007 (9)	−0.0019 (8)
C16	0.0419 (13)	0.0449 (13)	0.0228 (10)	0.0039 (10)	0.0002 (9)	−0.0021 (9)
C17	0.0329 (11)	0.0451 (13)	0.0284 (11)	0.0006 (10)	0.0059 (9)	−0.0150 (10)
C18	0.0283 (10)	0.0330 (11)	0.0400 (12)	0.0068 (9)	0.0025 (9)	−0.0083 (10)
C19	0.0261 (10)	0.0292 (10)	0.0287 (10)	0.0027 (8)	−0.0029 (8)	−0.0039 (8)
C20	0.0276 (9)	0.0180 (9)	0.0191 (9)	−0.0041 (7)	−0.0018 (7)	0.0010 (7)
C21	0.0368 (11)	0.0191 (9)	0.0213 (9)	0.0043 (8)	−0.0013 (8)	−0.0022 (7)
C22	0.0479 (13)	0.0206 (9)	0.0223 (10)	0.0003 (9)	−0.0040 (9)	0.0026 (8)
C23	0.0452 (12)	0.0243 (10)	0.0215 (9)	−0.0072 (9)	0.0054 (9)	0.0021 (8)
C24	0.0370 (11)	0.0273 (11)	0.0318 (11)	0.0024 (9)	0.0095 (9)	−0.0007 (9)
C25	0.0317 (10)	0.0221 (9)	0.0298 (10)	0.0028 (8)	0.0011 (8)	0.0037 (8)

F1—C11	1.365 (2)	C15—C16	1.387 (3)
F2—C17	1.366 (3)	C16—C17	1.373 (3)
O1—C1	1.234 (2)	C17—C18	1.373 (3)
N1—N2	1.400 (2)	C18—C19	1.385 (3)
N1—C1	1.390 (2)	C20—C25	1.387 (3)
N1—C20	1.415 (2)	C20—C21	1.388 (3)
N2—C7	1.367 (3)	C21—C22	1.388 (3)
N2—HN2	0.859 (18)	C22—C23	1.376 (3)
C1—C2	1.451 (3)	C23—C24	1.384 (3)
C2—C3	1.419 (3)	C24—C25	1.387 (3)
C2—C7	1.391 (3)	C4—H4	0.9300
C3—C4	1.384 (3)	C6—H6	0.9300
C3—C8	1.487 (3)	C9—H9	0.9300
C4—C5	1.433 (3)	C10—H10	0.9300
C5—C14	1.486 (3)	C12—H12	0.9300
C5—C6	1.379 (3)	C13—H13	0.9300
C6—C7	1.402 (3)	C15—H15	0.9300
C8—C13	1.386 (3)	C16—H16	0.9300
C8—C9	1.394 (3)	C18—H18	0.9300
C9—C10	1.384 (3)	C19—H19	0.9300
C10—C11	1.368 (3)	C21—H21	0.9300
C11—C12	1.364 (3)	C22—H22	0.9300
C12—C13	1.383 (3)	C23—H23	0.9300
C14—C15	1.396 (3)	C24—H24	0.9300
C14—C19	1.400 (3)	C25—H25	0.9300
N2—N1—C1	111.25 (15)	C17—C18—C19	118.4 (2)
N2—N1—C20	119.12 (14)	C14—C19—C18	121.05 (19)
C1—N1—C20	127.78 (15)	N1—C20—C21	119.13 (17)
N1—N2—C7	106.38 (14)	C21—C20—C25	120.29 (18)
C7—N2—HN2	123.5 (17)	N1—C20—C25	120.58 (17)
N1—N2—HN2	114.3 (15)	C20—C21—C22	119.36 (18)
N1—C1—C2	104.38 (15)	C21—C22—C23	120.86 (19)
O1—C1—C2	131.73 (18)	C22—C23—C24	119.36 (19)
O1—C1—N1	123.89 (18)	C23—C24—C25	120.8 (2)
C1—C2—C3	132.02 (18)	C20—C25—C24	119.32 (18)
C1—C2—C7	107.51 (16)	C3—C4—H4	119.00
C3—C2—C7	120.41 (18)	C5—C4—H4	119.00
C2—C3—C4	117.28 (18)	C5—C6—H6	121.00
C4—C3—C8	121.73 (18)	C7—C6—H6	121.00
C2—C3—C8	120.85 (18)	C8—C9—H9	120.00
C3—C4—C5	121.89 (18)	C10—C9—H9	120.00
C4—C5—C6	119.97 (17)	C9—C10—H10	121.00
C4—C5—C14	119.84 (17)	C11—C10—H10	121.00
C6—C5—C14	120.19 (17)	C11—C12—H12	121.00
C5—C6—C7	118.29 (17)	C13—C12—H12	121.00
C2—C7—C6	121.95 (17)	C8—C13—H13	120.00
N2—C7—C6	128.04 (17)	C12—C13—H13	119.00
N2—C7—C2	110.00 (16)	C14—C15—H15	119.00
C3—C8—C13	122.36 (18)	C16—C15—H15	119.00
C9—C8—C13	118.64 (18)	C15—C16—H16	121.00
C3—C8—C9	118.97 (18)	C17—C16—H16	121.00
C8—C9—C10	120.81 (19)	C17—C18—H18	121.00
C9—C10—C11	118.2 (2)	C19—C18—H18	121.00
F1—C11—C10	118.9 (2)	C14—C19—H19	119.00
C10—C11—C12	123.0 (2)	C18—C19—H19	119.00
F1—C11—C12	118.0 (2)	C20—C21—H21	120.00
C11—C12—C13	118.3 (2)	C22—C21—H21	120.00
C8—C13—C12	121.0 (2)	C21—C22—H22	120.00
C15—C14—C19	118.13 (18)	C23—C22—H22	119.00
C5—C14—C15	121.30 (18)	C22—C23—H23	120.00
C5—C14—C19	120.55 (17)	C24—C23—H23	120.00
C14—C15—C16	121.40 (19)	C23—C24—H24	120.00
C15—C16—C17	118.1 (2)	C25—C24—H24	120.00
F2—C17—C18	118.3 (2)	C20—C25—H25	120.00
C16—C17—C18	122.9 (2)	C24—C25—H25	120.00
F2—C17—C16	118.77 (19)
C1—N1—N2—C7	5.3 (2)	C6—C5—C14—C19	35.8 (3)
C20—N1—N2—C7	171.01 (17)	C4—C5—C14—C19	−143.24 (19)
N2—N1—C1—O1	178.1 (2)	C4—C5—C6—C7	−2.7 (3)
C20—N1—C1—O1	14.0 (3)	C4—C5—C14—C15	38.4 (3)
N2—N1—C1—C2	−1.4 (2)	C5—C6—C7—N2	179.9 (2)
C20—N1—C1—C2	−165.57 (19)	C5—C6—C7—C2	−1.2 (3)
C1—N1—C20—C25	−35.8 (3)	C3—C8—C9—C10	−177.9 (2)
N2—N1—C20—C21	−18.2 (3)	C3—C8—C13—C12	178.4 (2)
C1—N1—C20—C21	144.9 (2)	C9—C8—C13—C12	0.5 (3)
N2—N1—C20—C25	161.15 (18)	C13—C8—C9—C10	0.1 (3)
N1—N2—C7—C6	171.78 (19)	C8—C9—C10—C11	−0.5 (3)
N1—N2—C7—C2	−7.2 (2)	C9—C10—C11—F1	−179.0 (2)
N1—C1—C2—C3	−180.0 (2)	C9—C10—C11—C12	0.4 (4)
N1—C1—C2—C7	−3.0 (2)	C10—C11—C12—C13	0.2 (4)
O1—C1—C2—C3	0.5 (4)	F1—C11—C12—C13	179.6 (2)
O1—C1—C2—C7	177.5 (2)	C11—C12—C13—C8	−0.7 (4)
C1—C2—C7—C6	−172.62 (19)	C19—C14—C15—C16	−0.4 (3)
C1—C2—C7—N2	6.4 (2)	C5—C14—C19—C18	−177.86 (19)
C1—C2—C3—C4	172.4 (2)	C5—C14—C15—C16	178.00 (19)
C3—C2—C7—N2	−176.14 (19)	C15—C14—C19—C18	0.5 (3)
C3—C2—C7—C6	4.8 (3)	C14—C15—C16—C17	0.2 (3)
C7—C2—C3—C8	171.4 (2)	C15—C16—C17—F2	179.7 (2)
C1—C2—C3—C8	−11.9 (4)	C15—C16—C17—C18	−0.1 (3)
C7—C2—C3—C4	−4.3 (3)	C16—C17—C18—C19	0.3 (3)
C4—C3—C8—C9	127.1 (2)	F2—C17—C18—C19	−179.50 (19)
C2—C3—C4—C5	0.5 (3)	C17—C18—C19—C14	−0.5 (3)
C4—C3—C8—C13	−50.8 (3)	N1—C20—C21—C22	179.20 (18)
C2—C3—C8—C13	133.7 (2)	C25—C20—C21—C22	−0.1 (3)
C2—C3—C8—C9	−48.4 (3)	N1—C20—C25—C24	−179.86 (18)
C8—C3—C4—C5	−175.18 (19)	C21—C20—C25—C24	−0.6 (3)
C3—C4—C5—C6	3.0 (3)	C20—C21—C22—C23	0.7 (3)
C3—C4—C5—C14	−177.90 (19)	C21—C22—C23—C24	−0.6 (3)
C6—C5—C14—C15	−142.5 (2)	C22—C23—C24—C25	−0.1 (3)
C14—C5—C6—C7	178.28 (17)	C23—C24—C25—C20	0.7 (3)

Cg5 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O1i	0.86 (2)	2.00 (2)	2.830 (2)	162 (2)
C6—H6···F1ii	0.93	2.49	3.362 (2)	156
C21—H21···N2	0.93	2.48	2.799 (3)	100
C25—H25···O1	0.93	2.43	2.941 (3)	115
C15—H15···Cg5iii	0.93	2.85	3.656 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C20–C25 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯O1i	0.86 (2)	2.00 (2)	2.830 (2)	162 (2)
C6—H6⋯F1ii	0.93	2.49	3.362 (2)	156
C15—H15⋯Cg5iii	0.93	2.85	3.656 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) .