Propan-2-yl r-4-(4-fluoro-phen-yl)-3-hy-droxy-c-6-methyl-2-phenyl-4,5-dihydro-2H-indazole-t-5-carboxyl-ate.

In the title compound, C(24)H(23)FN(2)O(3), the cyclo-hexene ring adopts a screw-boat conformation. The fluorobenzene ring attached to the cyclo-hexene ring and the phenyl ring attached to the indazole moiety are inclined to one another by 57.77 (13)°. In the crystal, mol-ecules are linked by O-H⋯N and C-H⋯O hydrogen bonds, forming chains with C(5) and C(10) graph-set motifs. There are also C-H⋯π inter-actions present. The isopropoxycarbonyl group undergoes considerable thermal motion.

Related literature

For examples of the biological activities of indazole derivatatives, see: Jain et al. (1987 ▶); Palazzo et al. (1966 ▶); Popat et al. (2003 ▶); Beylin et al. (1991 ▶); George et al. (1998 ▶); Roman (1990 ▶). For the crystal structure of a similar compound, namely 4,6-bis­(4-fluoro­phen­yl)-2-phenyl-1H-indazol-3(2H)-one, see: Butcher et al. (2011 ▶). For information on graph-set motifs, see: Bernstein et al. (1995 ▶). For information on ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H23FN2O3

M = 406.44

Monoclinic,

a = 17.640 (1) Å

b = 11.0295 (6) Å

c = 11.3791 (6) Å

β = 99.133 (1)°

V = 2185.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

20548 measured reflections

3843 independent reflections

2970 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.135

S = 1.03

3843 reflections

279 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039955/su2500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039955/su2500Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039955/su2500Isup3.cml

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

C24H23FN2O3	F(000) = 856
Mr = 406.44	Dx = 1.235 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3844 reflections
a = 17.640 (1) Å	θ = 2–25°
b = 11.0295 (6) Å	µ = 0.09 mm−1
c = 11.3791 (6) Å	T = 293 K
β = 99.133 (1)°	Block, colourless
V = 2185.9 (2) Å3	0.35 × 0.25 × 0.25 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω scan	h = −20→20
20548 measured reflections	k = −13→13
3843 independent reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.9373P] where P = (Fo2 + 2Fc2)/3
3843 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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	Occ. (<1)
F	0.55203 (11)	0.4061 (2)	0.2222 (2)	0.1378 (9)
O1	0.14456 (9)	0.32293 (13)	0.05959 (11)	0.0505 (4)
H1	0.1609	0.2941	0.1252	0.076*
O51	0.26507 (13)	−0.19468 (16)	−0.01810 (17)	0.0885 (6)
O52	0.2223 (4)	−0.1001 (5)	0.1280 (9)	0.116 (2)	0.724 (15)
O52'	0.1999 (12)	−0.0778 (13)	0.0673 (18)	0.116 (2)	0.276 (15)
N2	0.14598 (9)	0.28868 (14)	−0.13981 (12)	0.0369 (4)
N1	0.18599 (9)	0.22532 (14)	−0.21440 (12)	0.0386 (4)
C3	0.17400 (10)	0.26286 (16)	−0.02333 (14)	0.0356 (4)
C4	0.28913 (11)	0.12354 (17)	0.07402 (16)	0.0376 (4)
H4	0.2638	0.1076	0.1431	0.045*
C5	0.31565 (12)	0.00027 (17)	0.02803 (17)	0.0430 (5)
H5	0.3642	−0.0202	0.0788	0.052*
C6	0.33235 (12)	0.00401 (18)	−0.09910 (18)	0.0453 (5)
C7	0.29229 (12)	0.07767 (18)	−0.17831 (17)	0.0443 (5)
H7	0.3004	0.0767	−0.2571	0.053*
C8	0.23623 (10)	0.15914 (16)	−0.14217 (15)	0.0362 (4)
C9	0.23134 (10)	0.17912 (16)	−0.02211 (15)	0.0351 (4)
C21	0.08425 (11)	0.36638 (17)	−0.18736 (16)	0.0396 (4)
C22	0.09024 (13)	0.4340 (2)	−0.28730 (18)	0.0538 (6)
H22	0.1342	0.4292	−0.3226	0.065*
C23	0.03079 (16)	0.5085 (2)	−0.3344 (2)	0.0722 (7)
H23	0.0347	0.5539	−0.4021	0.087*
C24	−0.03366 (17)	0.5169 (3)	−0.2835 (3)	0.0826 (9)
H24	−0.0738	0.5671	−0.3165	0.099*
C25	−0.03905 (15)	0.4505 (3)	−0.1829 (3)	0.0794 (8)
H25	−0.0828	0.4571	−0.1472	0.095*
C26	0.01950 (13)	0.3744 (2)	−0.1345 (2)	0.0589 (6)
H26	0.0154	0.3289	−0.0669	0.071*
C41	0.35810 (11)	0.20446 (17)	0.11368 (17)	0.0424 (5)
C42	0.40331 (13)	0.1842 (2)	0.2224 (2)	0.0575 (6)
H42	0.3898	0.1232	0.2715	0.069*
C43	0.46809 (15)	0.2525 (3)	0.2599 (3)	0.0768 (8)
H43	0.4980	0.2382	0.3335	0.092*
C44	0.48710 (16)	0.3400 (3)	0.1879 (3)	0.0832 (9)
C45	0.44411 (19)	0.3651 (3)	0.0811 (3)	0.0933 (10)
H45	0.4582	0.4270	0.0335	0.112*
C46	0.37878 (15)	0.2966 (2)	0.0444 (2)	0.0690 (7)
H46	0.3485	0.3134	−0.0284	0.083*
C51	0.25938 (15)	−0.0996 (2)	0.0456 (2)	0.0570 (6)
C52	0.2159 (2)	−0.3005 (3)	−0.0069 (3)	0.0973 (11)
H52	0.2039	−0.3045	0.0742	0.117*
C53	0.1431 (3)	−0.2891 (4)	−0.0942 (4)	0.1460 (17)
H53A	0.1171	−0.2157	−0.0786	0.219*
H53B	0.1105	−0.3574	−0.0861	0.219*
H53C	0.1550	−0.2868	−0.1736	0.219*
C54	0.2622 (3)	−0.4083 (3)	−0.0300 (5)	0.176 (2)
H54A	0.2719	−0.4060	−0.1106	0.264*
H54B	0.2344	−0.4809	−0.0177	0.264*
H54C	0.3101	−0.4076	0.0235	0.264*
C61	0.39422 (15)	−0.0780 (2)	−0.1293 (2)	0.0732 (8)
H61A	0.3978	−0.0699	−0.2122	0.110*
H61B	0.3821	−0.1605	−0.1127	0.110*
H61C	0.4424	−0.0562	−0.0823	0.110*

	U11	U22	U33	U12	U13	U23
F	0.0942 (13)	0.1364 (18)	0.175 (2)	−0.0579 (13)	−0.0032 (13)	−0.0562 (16)
O1	0.0724 (10)	0.0546 (9)	0.0250 (7)	0.0222 (7)	0.0091 (6)	0.0010 (6)
O51	0.1363 (17)	0.0548 (11)	0.0841 (13)	−0.0338 (11)	0.0475 (12)	−0.0155 (9)
O52	0.190 (5)	0.060 (2)	0.130 (5)	−0.038 (2)	0.120 (5)	−0.015 (3)
O52'	0.190 (5)	0.060 (2)	0.130 (5)	−0.038 (2)	0.120 (5)	−0.015 (3)
N2	0.0446 (9)	0.0414 (9)	0.0246 (7)	0.0058 (7)	0.0059 (6)	0.0001 (6)
N1	0.0469 (9)	0.0430 (9)	0.0267 (8)	0.0047 (7)	0.0086 (7)	−0.0009 (7)
C3	0.0464 (11)	0.0372 (10)	0.0232 (9)	−0.0012 (8)	0.0061 (8)	−0.0001 (7)
C4	0.0446 (11)	0.0376 (10)	0.0310 (9)	0.0030 (8)	0.0069 (8)	0.0035 (8)
C5	0.0473 (11)	0.0386 (11)	0.0419 (11)	0.0041 (9)	0.0038 (9)	0.0050 (8)
C6	0.0508 (12)	0.0374 (11)	0.0502 (12)	0.0023 (9)	0.0156 (10)	−0.0006 (9)
C7	0.0554 (12)	0.0447 (11)	0.0358 (10)	0.0026 (10)	0.0167 (9)	−0.0001 (9)
C8	0.0424 (10)	0.0357 (10)	0.0308 (9)	−0.0002 (8)	0.0069 (8)	0.0005 (8)
C9	0.0421 (10)	0.0347 (10)	0.0278 (9)	0.0000 (8)	0.0039 (8)	0.0007 (7)
C21	0.0466 (11)	0.0391 (10)	0.0318 (9)	0.0043 (9)	0.0020 (8)	−0.0020 (8)
C22	0.0616 (14)	0.0564 (13)	0.0436 (12)	0.0109 (11)	0.0086 (10)	0.0102 (10)
C23	0.0874 (19)	0.0681 (17)	0.0581 (15)	0.0247 (15)	0.0020 (14)	0.0201 (12)
C24	0.0769 (19)	0.0825 (19)	0.084 (2)	0.0399 (16)	−0.0019 (15)	0.0140 (16)
C25	0.0602 (16)	0.097 (2)	0.0829 (19)	0.0294 (15)	0.0176 (14)	0.0055 (17)
C26	0.0548 (13)	0.0712 (16)	0.0519 (13)	0.0120 (12)	0.0126 (11)	0.0084 (11)
C41	0.0474 (11)	0.0405 (11)	0.0393 (10)	0.0046 (9)	0.0064 (9)	−0.0047 (9)
C42	0.0580 (14)	0.0562 (14)	0.0531 (13)	0.0080 (11)	−0.0070 (11)	−0.0061 (11)
C43	0.0652 (17)	0.0789 (19)	0.0766 (18)	0.0082 (15)	−0.0182 (14)	−0.0249 (16)
C44	0.0624 (17)	0.084 (2)	0.100 (2)	−0.0204 (15)	0.0017 (16)	−0.0396 (19)
C45	0.106 (2)	0.086 (2)	0.089 (2)	−0.0484 (19)	0.0201 (19)	−0.0070 (17)
C46	0.0818 (17)	0.0691 (16)	0.0535 (14)	−0.0267 (14)	0.0024 (12)	0.0025 (12)
C51	0.0759 (16)	0.0414 (12)	0.0585 (14)	0.0012 (11)	0.0251 (12)	0.0012 (10)
C52	0.142 (3)	0.0652 (19)	0.088 (2)	−0.047 (2)	0.029 (2)	−0.0090 (16)
C53	0.155 (4)	0.104 (3)	0.172 (4)	−0.040 (3)	0.003 (3)	−0.014 (3)
C54	0.198 (5)	0.054 (2)	0.274 (7)	−0.019 (3)	0.033 (5)	−0.004 (3)
C61	0.0776 (17)	0.0674 (16)	0.0804 (18)	0.0276 (14)	0.0305 (14)	0.0079 (14)

F—C44	1.361 (3)	C23—H23	0.9300
O1—C3	1.325 (2)	C24—C25	1.375 (4)
O1—H1	0.8200	C24—H24	0.9300
O51—C51	1.288 (3)	C25—C26	1.376 (3)
O51—C52	1.472 (3)	C25—H25	0.9300
O52—C51	1.225 (7)	C26—H26	0.9300
O52'—C51	1.142 (18)	C41—C46	1.371 (3)
N2—C3	1.369 (2)	C41—C42	1.380 (3)
N2—N1	1.377 (2)	C42—C43	1.378 (4)
N2—C21	1.423 (2)	C42—H42	0.9300
N1—C8	1.328 (2)	C43—C44	1.343 (4)
C3—C9	1.368 (3)	C43—H43	0.9300
C4—C9	1.502 (2)	C44—C45	1.354 (4)
C4—C41	1.519 (3)	C45—C46	1.386 (4)
C4—C5	1.555 (3)	C45—H45	0.9300
C4—H4	0.9800	C46—H46	0.9300
C5—C51	1.517 (3)	C52—C54	1.489 (6)
C5—C6	1.522 (3)	C52—C53	1.499 (5)
C5—H5	0.9800	C52—H52	0.9800
C6—C7	1.330 (3)	C53—H53A	0.9600
C6—C61	1.499 (3)	C53—H53B	0.9600
C7—C8	1.444 (3)	C53—H53C	0.9600
C7—H7	0.9300	C54—H54A	0.9600
C8—C9	1.400 (2)	C54—H54B	0.9600
C21—C26	1.376 (3)	C54—H54C	0.9600
C21—C22	1.378 (3)	C61—H61A	0.9600
C22—C23	1.372 (3)	C61—H61B	0.9600
C22—H22	0.9300	C61—H61C	0.9600
C23—C24	1.358 (4)
C3—O1—H1	109.5	C25—C26—H26	120.5
C51—O51—C52	119.8 (2)	C46—C41—C42	117.8 (2)
C3—N2—N1	110.45 (14)	C46—C41—C4	122.59 (18)
C3—N2—C21	129.06 (15)	C42—C41—C4	119.56 (19)
N1—N2—C21	120.48 (14)	C43—C42—C41	121.5 (2)
C8—N1—N2	104.75 (13)	C43—C42—H42	119.3
O1—C3—C9	134.69 (16)	C41—C42—H42	119.3
O1—C3—N2	117.61 (16)	C44—C43—C42	118.6 (3)
C9—C3—N2	107.64 (15)	C44—C43—H43	120.7
C9—C4—C41	113.30 (15)	C42—C43—H43	120.7
C9—C4—C5	108.49 (15)	C43—C44—C45	122.4 (3)
C41—C4—C5	110.14 (15)	C43—C44—F	119.3 (3)
C9—C4—H4	108.3	C45—C44—F	118.3 (3)
C41—C4—H4	108.3	C44—C45—C46	118.7 (3)
C5—C4—H4	108.3	C44—C45—H45	120.7
C51—C5—C6	111.98 (17)	C46—C45—H45	120.7
C51—C5—C4	110.64 (16)	C41—C46—C45	121.0 (3)
C6—C5—C4	114.21 (15)	C41—C46—H46	119.5
C51—C5—H5	106.5	C45—C46—H46	119.5
C6—C5—H5	106.5	O52'—C51—O52	38.2 (9)
C4—C5—H5	106.5	O52'—C51—O51	116.8 (8)
C7—C6—C61	122.76 (19)	O52—C51—O51	121.7 (3)
C7—C6—C5	119.90 (17)	O52'—C51—C5	121.2 (7)
C61—C6—C5	117.34 (18)	O52—C51—C5	123.0 (3)
C6—C7—C8	120.09 (17)	O51—C51—C5	114.0 (2)
C6—C7—H7	120.0	O51—C52—C54	105.7 (3)
C8—C7—H7	120.0	O51—C52—C53	109.3 (3)
N1—C8—C9	112.28 (16)	C54—C52—C53	112.7 (3)
N1—C8—C7	125.88 (16)	O51—C52—H52	109.7
C9—C8—C7	121.81 (17)	C54—C52—H52	109.7
C3—C9—C8	104.85 (15)	C53—C52—H52	109.7
C3—C9—C4	134.26 (16)	C52—C53—H53A	109.5
C8—C9—C4	120.43 (16)	C52—C53—H53B	109.5
C26—C21—C22	120.27 (19)	H53A—C53—H53B	109.5
C26—C21—N2	120.68 (18)	C52—C53—H53C	109.5
C22—C21—N2	119.04 (18)	H53A—C53—H53C	109.5
C23—C22—C21	119.5 (2)	H53B—C53—H53C	109.5
C23—C22—H22	120.2	C52—C54—H54A	109.5
C21—C22—H22	120.2	C52—C54—H54B	109.5
C24—C23—C22	120.9 (2)	H54A—C54—H54B	109.5
C24—C23—H23	119.5	C52—C54—H54C	109.5
C22—C23—H23	119.5	H54A—C54—H54C	109.5
C23—C24—C25	119.5 (2)	H54B—C54—H54C	109.5
C23—C24—H24	120.3	C6—C61—H61A	109.5
C25—C24—H24	120.3	C6—C61—H61B	109.5
C24—C25—C26	120.8 (2)	H61A—C61—H61B	109.5
C24—C25—H25	119.6	C6—C61—H61C	109.5
C26—C25—H25	119.6	H61A—C61—H61C	109.5
C21—C26—C25	119.1 (2)	H61B—C61—H61C	109.5
C21—C26—H26	120.5
C3—N2—N1—C8	1.81 (19)	N1—N2—C21—C22	−38.0 (3)
C21—N2—N1—C8	−177.34 (16)	C26—C21—C22—C23	−0.7 (3)
N1—N2—C3—O1	175.77 (16)	N2—C21—C22—C23	179.5 (2)
C21—N2—C3—O1	−5.2 (3)	C21—C22—C23—C24	0.3 (4)
N1—N2—C3—C9	−1.8 (2)	C22—C23—C24—C25	0.5 (5)
C21—N2—C3—C9	177.29 (17)	C23—C24—C25—C26	−1.1 (5)
C9—C4—C5—C51	−83.40 (19)	C22—C21—C26—C25	0.1 (4)
C41—C4—C5—C51	152.07 (17)	N2—C21—C26—C25	180.0 (2)
C9—C4—C5—C6	44.0 (2)	C24—C25—C26—C21	0.7 (4)
C41—C4—C5—C6	−80.5 (2)	C9—C4—C41—C46	−21.0 (3)
C51—C5—C6—C7	94.1 (2)	C5—C4—C41—C46	100.8 (2)
C4—C5—C6—C7	−32.6 (3)	C9—C4—C41—C42	160.39 (18)
C51—C5—C6—C61	−85.5 (2)	C5—C4—C41—C42	−77.9 (2)
C4—C5—C6—C61	147.7 (2)	C46—C41—C42—C43	−1.2 (3)
C61—C6—C7—C8	−176.7 (2)	C4—C41—C42—C43	177.5 (2)
C5—C6—C7—C8	3.7 (3)	C41—C42—C43—C44	−0.2 (4)
N2—N1—C8—C9	−1.2 (2)	C42—C43—C44—C45	1.4 (5)
N2—N1—C8—C7	−179.28 (17)	C42—C43—C44—F	−178.3 (2)
C6—C7—C8—N1	−170.79 (19)	C43—C44—C45—C46	−0.9 (5)
C6—C7—C8—C9	11.3 (3)	F—C44—C45—C46	178.7 (3)
O1—C3—C9—C8	−176.0 (2)	C42—C41—C46—C45	1.6 (4)
N2—C3—C9—C8	1.0 (2)	C4—C41—C46—C45	−177.0 (2)
O1—C3—C9—C4	−4.1 (4)	C44—C45—C46—C41	−0.6 (5)
N2—C3—C9—C4	172.85 (19)	C52—O51—C51—O52'	−33.0 (12)
N1—C8—C9—C3	0.2 (2)	C52—O51—C51—O52	10.8 (7)
C7—C8—C9—C3	178.33 (17)	C52—O51—C51—C5	177.8 (2)
N1—C8—C9—C4	−173.10 (16)	C6—C5—C51—O52'	−114.5 (13)
C7—C8—C9—C4	5.1 (3)	C4—C5—C51—O52'	14.1 (13)
C41—C4—C9—C3	−80.1 (3)	C6—C5—C51—O52	−160.0 (6)
C5—C4—C9—C3	157.3 (2)	C4—C5—C51—O52	−31.3 (7)
C41—C4—C9—C8	90.8 (2)	C6—C5—C51—O51	33.2 (3)
C5—C4—C9—C8	−31.8 (2)	C4—C5—C51—O51	161.8 (2)
C3—N2—C21—C26	−36.8 (3)	C51—O51—C52—C54	−148.1 (3)
N1—N2—C21—C26	142.2 (2)	C51—O51—C52—C53	90.4 (4)
C3—N2—C21—C22	143.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.82	2.6143 (18)	162
C22—H22···O52ii	0.93	2.56	3.229 (6)	129
C24—H24···Cg1iii	0.93	2.77	3.694 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C3/C8/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.82	2.6143 (18)	162
C22—H22⋯O52ii	0.93	2.56	3.229 (6)	129
C24—H24⋯Cg1iii	0.93	2.77	3.694 (3)	174

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