organic compounds
Propan-2-yl r-4-(4-fluorophenyl)-3-hydroxy-c-6-methyl-2-phenyl-4,5-dihydro-2H-indazole-t-5-carboxylate
aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India, and cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
*Correspondence e-mail: raghema2000@yahoo.co.in
In the title compound, C24H23FN2O3, the cyclohexene ring adopts a screw-boat conformation. The fluorobenzene ring attached to the cyclohexene ring and the phenyl ring attached to the indazole moiety are inclined to one another by 57.77 (13)°. In the crystal, molecules 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 interactions 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 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
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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).
Supporting information
https://doi.org/10.1107/S1600536812039955/su2500sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039955/su2500Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039955/su2500Isup3.cml
A mixture of isopropyl acetoacetate(14.4 g, 100 mmol), 4-fluorobenzaldehyde(6.2 g, 50 mmol) and methylamine(1.55 g, 50 mmol) in ethanol(50 ml) was heated to boiling. The reaction mixture was kept overnight and the solid that seperated out was filtered off and purified by recrystallization from ethanol. 9.5 g (25 mmmol) of this product, r(2),c(4)-bis(isopropoxycarbonyl)-c(5)-hydroxy-t(5)- methyl-t(3)-(4'-fluorophenyl)cyclohexanone (yeild 14.8 g, 78%, M.p. 452 K), was dissolved in acetic acid and after the addition of phenylhydrazine (4.3 g, 40 mmol) in the presence of sodium acetate (2.9 g, 50 mmol), the reaction mixture was refluxed for 4 h. The solution was cooled and then poured into crushed ice. The precipitated solid was filtered off by suction (yield 70%, M.p. 493 K) and recrystallized from ethanol giving block-like colourless crystals.
The isopropycarboxylate group undergoes considerable thermal motion. Atom O52 was refined as disordered over two positions (O52/O52') and had a final refined occupancy ratio of 0.724 (15):0.276 (15). The C-bound H-atoms were included in calculated positions and treated as riding atoms: O-H = 0.82 Å, C-H = 0.93, 0.98 and 0.96 Å for CH(aromatic), CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for OH and CH3 H-atoms and = 1.2 for other H-atoms. Reflection 1 0 0 was partially obscured by the beam stop and was omitted.
Indazole derivatives possess a wide spectrum of pharmacological activities, such as analgestic, anti-inflammatory, anti-depressant, anti-hypertensive, anti-viral and anti-cancer (Jain et al., 1987; Palazzo et al., 1966; Popat et al., 2003; Beylin et al., 1991; George et al., 1998; Roman, 1990). In the view of these important attributes, the title compound was synthesized and its
is described herein.In the title molecule, Fig. 1, the cyclohexene ring adopts a scew-boat conformation with puckering parameters: Q = 0.391 (2) Å,θ = 61.7 (3)° and φ = 28.7 (3)° (Cremer & Pople, 1975). The methyl group attached at C6 is substituted in the β equitorial position [C8—C7—C6—C61 = 176.7 (2)°]. The pyrazole ring (N1/N2/C3/C8/C9) is almost planar with a maximum deviation of 0.010 (2) Å for atom N2. This five membered ring and the attached phenyl (C21-C26) ring make a dihedral angle of 37.51 (12)°. The same phenyl ring makes a dihedral angle of 57.77 (13)° with the fluorophenyl ring (C41-C46). This is similar to the situation in a related structure, 4,6-Bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one (Butcher et al., 2011), where the same angle is 57.69 (10)°.
In the crystal, molecules are linked by O—H···N and weak C— H···O hydrogen bonds, forming chains with C(5) and C(10) graph-set motifs (Bernstein et al., 1995) [Table 1 and Fig. 2]. There are also C-H···π interactions present (Table 1).
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
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).Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).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 |
C24H23FN2O3 | V = 2185.9 (2) Å3 |
Mr = 406.44 | Z = 4 |
Monoclinic, P2/c | Mo Kα radiation |
a = 17.640 (1) Å | µ = 0.09 mm−1 |
b = 11.0295 (6) Å | T = 293 K |
c = 11.3791 (6) Å | 0.35 × 0.25 × 0.25 mm |
β = 99.133 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 2970 reflections with I > 2σ(I) |
20548 measured reflections | Rint = 0.034 |
3843 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.34 e Å−3 |
3843 reflections | Δρmin = −0.22 e Å−3 |
279 parameters |
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) |
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) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H23FN2O3 |
Mr | 406.44 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.640 (1), 11.0295 (6), 11.3791 (6) |
β (°) | 99.133 (1) |
V (Å3) | 2185.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20548, 3843, 2970 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.135, 1.03 |
No. of reflections | 3843 |
No. of parameters | 279 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.22 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SIR92 (Altomare et al., 1994), ORTEP-3 (Farrugia, 1999) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
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) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z−1/2. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Indazole derivatives possess a wide spectrum of pharmacological activities, such as analgestic, anti-inflammatory, anti-depressant, anti-hypertensive, anti-viral and anti-cancer (Jain et al., 1987; Palazzo et al., 1966; Popat et al., 2003; Beylin et al., 1991; George et al., 1998; Roman, 1990). In the view of these important attributes, the title compound was synthesized and its crystal structure is described herein.
In the title molecule, Fig. 1, the cyclohexene ring adopts a scew-boat conformation with puckering parameters: Q = 0.391 (2) Å,θ = 61.7 (3)° and φ = 28.7 (3)° (Cremer & Pople, 1975). The methyl group attached at C6 is substituted in the β equitorial position [C8—C7—C6—C61 = 176.7 (2)°]. The pyrazole ring (N1/N2/C3/C8/C9) is almost planar with a maximum deviation of 0.010 (2) Å for atom N2. This five membered ring and the attached phenyl (C21-C26) ring make a dihedral angle of 37.51 (12)°. The same phenyl ring makes a dihedral angle of 57.77 (13)° with the fluorophenyl ring (C41-C46). This is similar to the situation in a related structure, 4,6-Bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one (Butcher et al., 2011), where the same angle is 57.69 (10)°.
In the crystal, molecules are linked by O—H···N and weak C— H···O hydrogen bonds, forming chains with C(5) and C(10) graph-set motifs (Bernstein et al., 1995) [Table 1 and Fig. 2]. There are also C-H···π interactions present (Table 1).