organic compounds
2-[2-(2,6-Dichlorobenzyloxy)-2-phenylethyl]-2H-indazole
aDepartment of Chemistry, Bülent Ecevit University, 67100 Zonguldak, Turkey, bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr
In the title compound, C22H18Cl2N2O, the indazole ring system is approximately planar [maximum deviation = 0.031 (2) Å], its mean plane is oriented at 3.17 (4) and 19.34 (4)° with respect to the phenyl and benzene rings. In the crystal, weak C—H⋯π interactions link the molecules into supramolecular chains running along the b-axis direction.
CCDC reference: 989513
Related literature
For clinical uses of azole antifungals possessing an imidazole ring such as micozanole and econazole, see: Godefroi et al. (1969). Some indazole derivatives have been known as antifungal also, see: Lebouvier et al. (2007); Park et al. (2007). For related structures, see: Freer et al. (1986); Özel Güven et al. (2008, 2010, 2013); Peeters et al. (1979).
Experimental
Crystal data
|
|
Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 989513
10.1107/S1600536814004887/xu5774sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004887/xu5774Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004887/xu5774Isup3.cml
The title compound, (I), was synthesized by the reaction of 1-phenyl-2-(2H-indazol-2-yl)ethanol with NaH and appropriate benzyl halide. NaH (0.025 g, 0.63 mmol) was added in small fractions to a solution of alcohol (0.150 g, 0.63 mmol) in DMF (3-4 ml). Then, appropriate benzyl halide (0.151 g, 0.63 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, and the excess hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, small amount of water was added and extracted with methylene chloride. The organic layer was separated, dried over anhydrous sodium sulfate, and then evaporated to dryness. The crude residue was purified by
on a silica-gel column using hexane-ethyl acetate mixture (10:1) as The ether was recrystallized from 2-propanol to obtain colourless crystals suitable for X-ray analysis (yield; 0.178 g, 71%).Atom H9 (for C9) was located in a difference Fourier map and was refined freely. The remaining H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.98 Å for aromatic, methylene and methine H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C).
Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell
CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C22H18Cl2N2O | F(000) = 824 |
Mr = 397.28 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 14300 reflections |
a = 15.2399 (4) Å | θ = 3.2–28.7° |
b = 5.3814 (3) Å | µ = 0.36 mm−1 |
c = 23.0461 (6) Å | T = 294 K |
β = 90.871 (3)° | Block, colorless |
V = 1889.84 (13) Å3 | 0.35 × 0.20 × 0.15 mm |
Z = 4 |
Rigaku Saturn724+ diffractometer | 3685 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 28.7°, θmin = 3.2° |
ω scans | h = −18→20 |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011) | k = −7→5 |
Tmin = 0.918, Tmax = 0.948 | l = −30→30 |
18118 measured reflections | 3 standard reflections every 120 min |
4737 independent reflections | intensity decay: 1% |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0441P)2 + 1.2113P] where P = (Fo2 + 2Fc2)/3 |
4737 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.90 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C22H18Cl2N2O | V = 1889.84 (13) Å3 |
Mr = 397.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.2399 (4) Å | µ = 0.36 mm−1 |
b = 5.3814 (3) Å | T = 294 K |
c = 23.0461 (6) Å | 0.35 × 0.20 × 0.15 mm |
β = 90.871 (3)° |
Rigaku Saturn724+ diffractometer | 3685 reflections with I > 2σ(I) |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011) | Rint = 0.038 |
Tmin = 0.918, Tmax = 0.948 | 3 standard reflections every 120 min |
18118 measured reflections | intensity decay: 1% |
4737 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.90 e Å−3 |
4737 reflections | Δρmin = −0.39 e Å−3 |
248 parameters |
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 > 2sigma(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 | ||
Cl1 | 0.58707 (3) | 0.36179 (10) | 0.038690 (19) | 0.03077 (13) | |
Cl2 | 0.59584 (3) | −0.32700 (10) | 0.21081 (2) | 0.03171 (14) | |
O1 | 0.45045 (7) | 0.0767 (2) | 0.14650 (5) | 0.0203 (3) | |
N1 | 0.37932 (9) | 0.0888 (3) | 0.25917 (6) | 0.0175 (3) | |
N2 | 0.36785 (9) | −0.1165 (3) | 0.29187 (6) | 0.0192 (3) | |
C1 | 0.36816 (10) | −0.0354 (3) | 0.15680 (7) | 0.0180 (3) | |
H1 | 0.3777 | −0.2066 | 0.1699 | 0.022* | |
C2 | 0.30805 (10) | −0.0383 (3) | 0.10389 (7) | 0.0173 (3) | |
C3 | 0.24565 (11) | −0.2256 (4) | 0.09721 (7) | 0.0204 (4) | |
H3 | 0.2419 | −0.3505 | 0.1250 | 0.024* | |
C4 | 0.18898 (11) | −0.2275 (4) | 0.04948 (8) | 0.0226 (4) | |
H4 | 0.1473 | −0.3527 | 0.0454 | 0.027* | |
C5 | 0.19463 (11) | −0.0432 (4) | 0.00800 (7) | 0.0230 (4) | |
H5 | 0.1570 | −0.0448 | −0.0241 | 0.028* | |
C6 | 0.25637 (11) | 0.1439 (4) | 0.01424 (8) | 0.0236 (4) | |
H6 | 0.2600 | 0.2682 | −0.0137 | 0.028* | |
C7 | 0.31302 (11) | 0.1467 (4) | 0.06211 (7) | 0.0214 (4) | |
H7 | 0.3544 | 0.2729 | 0.0661 | 0.026* | |
C8 | 0.32805 (11) | 0.1131 (4) | 0.20580 (7) | 0.0208 (4) | |
H8A | 0.3250 | 0.2869 | 0.1948 | 0.025* | |
H8B | 0.2687 | 0.0551 | 0.2123 | 0.025* | |
C9 | 0.44260 (11) | 0.2432 (4) | 0.27907 (8) | 0.0213 (4) | |
H9 | 0.4532 (13) | 0.394 (4) | 0.2614 (9) | 0.026 (5)* | |
C10 | 0.42719 (10) | −0.0863 (3) | 0.33553 (7) | 0.0172 (3) | |
C11 | 0.44000 (11) | −0.2431 (4) | 0.38429 (7) | 0.0225 (4) | |
H11 | 0.4076 | −0.3881 | 0.3887 | 0.027* | |
C12 | 0.50195 (12) | −0.1731 (4) | 0.42472 (8) | 0.0249 (4) | |
H12 | 0.5111 | −0.2719 | 0.4574 | 0.030* | |
C13 | 0.55255 (11) | 0.0458 (4) | 0.41821 (8) | 0.0248 (4) | |
H13 | 0.5946 | 0.0856 | 0.4464 | 0.030* | |
C14 | 0.54104 (11) | 0.1992 (4) | 0.37171 (8) | 0.0241 (4) | |
H14 | 0.5747 | 0.3422 | 0.3678 | 0.029* | |
C15 | 0.47645 (10) | 0.1351 (3) | 0.32951 (7) | 0.0190 (4) | |
C16 | 0.50628 (10) | −0.0652 (4) | 0.10963 (7) | 0.0220 (4) | |
H16A | 0.4926 | −0.0320 | 0.0691 | 0.026* | |
H16B | 0.4992 | −0.2416 | 0.1168 | 0.026* | |
C17 | 0.59832 (10) | 0.0160 (4) | 0.12443 (7) | 0.0200 (4) | |
C18 | 0.64021 (11) | 0.2102 (4) | 0.09629 (7) | 0.0225 (4) | |
C19 | 0.72309 (12) | 0.2942 (4) | 0.11220 (8) | 0.0256 (4) | |
H19 | 0.7488 | 0.4252 | 0.0924 | 0.031* | |
C20 | 0.76702 (12) | 0.1802 (4) | 0.15798 (8) | 0.0254 (4) | |
H20 | 0.8229 | 0.2340 | 0.1688 | 0.031* | |
C21 | 0.72823 (11) | −0.0131 (4) | 0.18762 (7) | 0.0242 (4) | |
H21 | 0.7577 | −0.0902 | 0.2183 | 0.029* | |
C22 | 0.64479 (11) | −0.0904 (4) | 0.17093 (7) | 0.0223 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0290 (2) | 0.0384 (3) | 0.0247 (2) | 0.0036 (2) | −0.00486 (17) | 0.0070 (2) |
Cl2 | 0.0240 (2) | 0.0412 (3) | 0.0298 (2) | −0.0085 (2) | −0.00291 (17) | 0.0100 (2) |
O1 | 0.0146 (5) | 0.0249 (7) | 0.0213 (6) | −0.0006 (5) | 0.0014 (4) | −0.0040 (5) |
N1 | 0.0169 (6) | 0.0201 (8) | 0.0155 (6) | −0.0005 (6) | 0.0000 (5) | 0.0019 (6) |
N2 | 0.0184 (7) | 0.0199 (8) | 0.0194 (7) | −0.0031 (6) | −0.0007 (5) | 0.0021 (6) |
C1 | 0.0146 (7) | 0.0193 (10) | 0.0199 (8) | −0.0005 (6) | −0.0013 (6) | 0.0025 (7) |
C2 | 0.0137 (7) | 0.0183 (9) | 0.0197 (8) | 0.0026 (6) | −0.0004 (6) | −0.0009 (7) |
C3 | 0.0205 (8) | 0.0187 (10) | 0.0219 (8) | −0.0004 (7) | 0.0004 (6) | 0.0021 (7) |
C4 | 0.0195 (8) | 0.0207 (10) | 0.0275 (9) | −0.0021 (7) | −0.0029 (7) | −0.0043 (7) |
C5 | 0.0192 (8) | 0.0304 (11) | 0.0194 (8) | 0.0035 (7) | −0.0043 (6) | −0.0034 (7) |
C6 | 0.0243 (9) | 0.0246 (11) | 0.0219 (8) | 0.0022 (7) | −0.0023 (7) | 0.0050 (7) |
C7 | 0.0178 (8) | 0.0215 (10) | 0.0248 (8) | −0.0024 (7) | −0.0023 (6) | 0.0031 (7) |
C8 | 0.0160 (8) | 0.0290 (11) | 0.0173 (7) | 0.0038 (7) | −0.0023 (6) | 0.0020 (7) |
C9 | 0.0212 (8) | 0.0183 (10) | 0.0243 (8) | −0.0034 (7) | 0.0013 (7) | 0.0027 (7) |
C10 | 0.0159 (7) | 0.0182 (9) | 0.0175 (7) | 0.0002 (6) | 0.0004 (6) | −0.0014 (6) |
C11 | 0.0251 (9) | 0.0205 (10) | 0.0218 (8) | 0.0013 (7) | 0.0002 (7) | 0.0026 (7) |
C12 | 0.0267 (9) | 0.0268 (11) | 0.0209 (8) | 0.0081 (8) | −0.0027 (7) | 0.0012 (7) |
C13 | 0.0195 (8) | 0.0304 (11) | 0.0243 (8) | 0.0051 (7) | −0.0067 (7) | −0.0070 (8) |
C14 | 0.0189 (8) | 0.0230 (11) | 0.0303 (9) | −0.0029 (7) | −0.0020 (7) | −0.0051 (8) |
C15 | 0.0166 (7) | 0.0195 (10) | 0.0210 (8) | −0.0008 (7) | 0.0023 (6) | −0.0011 (7) |
C16 | 0.0166 (8) | 0.0303 (11) | 0.0192 (8) | 0.0020 (7) | −0.0005 (6) | −0.0058 (7) |
C17 | 0.0164 (8) | 0.0269 (11) | 0.0167 (7) | 0.0030 (7) | 0.0011 (6) | −0.0063 (7) |
C18 | 0.0212 (8) | 0.0300 (11) | 0.0162 (7) | 0.0047 (7) | −0.0002 (6) | −0.0012 (7) |
C19 | 0.0241 (9) | 0.0298 (12) | 0.0230 (8) | −0.0021 (8) | 0.0028 (7) | 0.0028 (8) |
C20 | 0.0194 (8) | 0.0341 (12) | 0.0226 (8) | −0.0024 (8) | −0.0020 (7) | −0.0010 (8) |
C21 | 0.0194 (8) | 0.0336 (12) | 0.0195 (8) | 0.0005 (7) | −0.0035 (6) | 0.0011 (8) |
C22 | 0.0186 (8) | 0.0297 (11) | 0.0188 (8) | 0.0005 (7) | 0.0007 (6) | −0.0009 (7) |
Cl1—C18 | 1.7467 (18) | C9—H9 | 0.92 (2) |
Cl2—C22 | 1.7446 (19) | C10—C11 | 1.417 (2) |
O1—C1 | 1.4150 (19) | C11—C12 | 1.369 (2) |
O1—C16 | 1.432 (2) | C11—H11 | 0.9300 |
N1—N2 | 1.350 (2) | C12—H12 | 0.9300 |
N1—C8 | 1.453 (2) | C13—C12 | 1.417 (3) |
N1—C9 | 1.348 (2) | C13—C14 | 1.362 (3) |
N2—C10 | 1.352 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.514 (2) | C14—H14 | 0.9300 |
C1—C8 | 1.519 (2) | C15—C9 | 1.392 (2) |
C1—H1 | 0.9800 | C15—C10 | 1.416 (2) |
C2—C7 | 1.388 (2) | C15—C14 | 1.416 (2) |
C3—C2 | 1.393 (2) | C16—H16A | 0.9700 |
C3—C4 | 1.388 (2) | C16—H16B | 0.9700 |
C3—H3 | 0.9300 | C17—C16 | 1.503 (2) |
C4—H4 | 0.9300 | C17—C18 | 1.390 (3) |
C5—C4 | 1.381 (3) | C17—C22 | 1.398 (2) |
C5—C6 | 1.384 (3) | C18—C19 | 1.386 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.391 (2) | C20—C19 | 1.384 (3) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—H7 | 0.9300 | C21—C20 | 1.382 (3) |
C8—H8A | 0.9700 | C21—C22 | 1.387 (2) |
C8—H8B | 0.9700 | C21—H21 | 0.9300 |
C1—O1—C16 | 114.10 (14) | C15—C10—C11 | 120.81 (16) |
N2—N1—C8 | 118.27 (14) | C10—C11—H11 | 121.3 |
C9—N1—N2 | 114.35 (14) | C12—C11—C10 | 117.45 (18) |
C9—N1—C8 | 127.25 (15) | C12—C11—H11 | 121.3 |
N1—N2—C10 | 103.07 (14) | C11—C12—C13 | 121.84 (17) |
O1—C1—C2 | 113.34 (13) | C11—C12—H12 | 119.1 |
O1—C1—C8 | 105.53 (14) | C13—C12—H12 | 119.1 |
O1—C1—H1 | 108.9 | C12—C13—H13 | 119.2 |
C2—C1—C8 | 111.02 (13) | C14—C13—C12 | 121.56 (17) |
C2—C1—H1 | 108.9 | C14—C13—H13 | 119.2 |
C8—C1—H1 | 108.9 | C13—C14—C15 | 118.20 (18) |
C3—C2—C1 | 120.00 (15) | C13—C14—H14 | 120.9 |
C7—C2—C1 | 120.84 (15) | C15—C14—H14 | 120.9 |
C7—C2—C3 | 119.15 (15) | C9—C15—C10 | 104.07 (15) |
C2—C3—H3 | 119.7 | C9—C15—C14 | 135.79 (18) |
C4—C3—C2 | 120.55 (17) | C14—C15—C10 | 120.12 (16) |
C4—C3—H3 | 119.7 | O1—C16—C17 | 105.74 (14) |
C3—C4—H4 | 120.0 | O1—C16—H16A | 110.6 |
C5—C4—C3 | 119.91 (17) | O1—C16—H16B | 110.6 |
C5—C4—H4 | 120.0 | C17—C16—H16A | 110.6 |
C4—C5—C6 | 120.00 (16) | C17—C16—H16B | 110.6 |
C4—C5—H5 | 120.0 | H16A—C16—H16B | 108.7 |
C6—C5—H5 | 120.0 | C18—C17—C16 | 123.10 (16) |
C5—C6—C7 | 120.22 (17) | C18—C17—C22 | 115.75 (15) |
C5—C6—H6 | 119.9 | C22—C17—C16 | 120.99 (17) |
C7—C6—H6 | 119.9 | C17—C18—Cl1 | 119.65 (13) |
C2—C7—C6 | 120.18 (17) | C19—C18—Cl1 | 117.32 (15) |
C2—C7—H7 | 119.9 | C19—C18—C17 | 123.03 (16) |
C6—C7—H7 | 119.9 | C18—C19—H19 | 120.5 |
N1—C8—C1 | 111.38 (13) | C20—C19—C18 | 119.05 (18) |
N1—C8—H8A | 109.4 | C20—C19—H19 | 120.5 |
N1—C8—H8B | 109.4 | C19—C20—H20 | 119.8 |
C1—C8—H8A | 109.4 | C21—C20—C19 | 120.30 (17) |
C1—C8—H8B | 109.4 | C21—C20—H20 | 119.8 |
H8A—C8—H8B | 108.0 | C20—C21—C22 | 119.08 (17) |
N1—C9—C15 | 106.30 (16) | C20—C21—H21 | 120.5 |
N1—C9—H9 | 121.4 (13) | C22—C21—H21 | 120.5 |
C15—C9—H9 | 132.1 (13) | C17—C22—Cl2 | 119.14 (13) |
N2—C10—C11 | 126.94 (17) | C21—C22—Cl2 | 118.07 (14) |
N2—C10—C15 | 112.20 (15) | C21—C22—C17 | 122.78 (18) |
C16—O1—C1—C2 | −69.95 (19) | C10—C11—C12—C13 | −0.8 (3) |
C16—O1—C1—C8 | 168.36 (13) | C14—C13—C12—C11 | 1.0 (3) |
C1—O1—C16—C17 | −155.79 (14) | C12—C13—C14—C15 | 0.2 (3) |
C8—N1—N2—C10 | 177.04 (14) | C10—C15—C9—N1 | −0.20 (18) |
C9—N1—N2—C10 | 0.86 (18) | C14—C15—C9—N1 | −178.25 (19) |
N2—N1—C8—C1 | −80.77 (18) | C9—C15—C10—N2 | 0.76 (19) |
C9—N1—C8—C1 | 94.9 (2) | C9—C15—C10—C11 | −176.80 (16) |
N2—N1—C9—C15 | −0.4 (2) | C14—C15—C10—N2 | 179.19 (15) |
C8—N1—C9—C15 | −176.19 (15) | C14—C15—C10—C11 | 1.6 (2) |
N1—N2—C10—C11 | 176.40 (16) | C9—C15—C14—C13 | 176.39 (19) |
N1—N2—C10—C15 | −0.98 (18) | C10—C15—C14—C13 | −1.4 (3) |
O1—C1—C2—C3 | 151.29 (16) | C18—C17—C16—O1 | −90.65 (19) |
O1—C1—C2—C7 | −29.9 (2) | C22—C17—C16—O1 | 84.6 (2) |
C8—C1—C2—C3 | −90.1 (2) | C16—C17—C18—Cl1 | −3.0 (2) |
C8—C1—C2—C7 | 88.65 (19) | C16—C17—C18—C19 | 176.14 (17) |
O1—C1—C8—N1 | −64.67 (18) | C22—C17—C18—Cl1 | −178.45 (13) |
C2—C1—C8—N1 | 172.15 (15) | C22—C17—C18—C19 | 0.7 (3) |
C1—C2—C7—C6 | −178.90 (16) | C16—C17—C22—Cl2 | 1.9 (2) |
C3—C2—C7—C6 | −0.1 (3) | C16—C17—C22—C21 | −177.02 (17) |
C4—C3—C2—C1 | 178.70 (15) | C18—C17—C22—Cl2 | 177.45 (13) |
C4—C3—C2—C7 | −0.1 (3) | C18—C17—C22—C21 | −1.4 (3) |
C2—C3—C4—C5 | 0.4 (3) | Cl1—C18—C19—C20 | 179.44 (15) |
C6—C5—C4—C3 | −0.4 (3) | C17—C18—C19—C20 | 0.3 (3) |
C4—C5—C6—C7 | 0.2 (3) | C21—C20—C19—C18 | −0.6 (3) |
C5—C6—C7—C2 | 0.1 (3) | C22—C21—C20—C19 | −0.2 (3) |
N2—C10—C11—C12 | −177.68 (17) | C20—C21—C22—Cl2 | −177.68 (15) |
C15—C10—C11—C12 | −0.5 (2) | C20—C21—C22—C17 | 1.2 (3) |
Cg2 and Cg3 are the centroids of the C2–C7 and C10–C15 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg3i | 0.93 | 2.91 | 3.591 (2) | 131 |
C11—H11···Cg2i | 0.93 | 2.87 | 3.616 (2) | 138 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Cg2 and Cg3 are the centroids of the C2–C7 and C10–C15 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg3i | 0.93 | 2.91 | 3.591 (2) | 131 |
C11—H11···Cg2i | 0.93 | 2.87 | 3.616 (2) | 138 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2012-10-03-12).
References
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350–1352. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Godefroi, E. F., Heeres, J., van Custem, J. & Janssen, P. A. (1969). J. Med. Chem. 12, 784–791. CrossRef CAS PubMed Web of Science Google Scholar
Lebouvier, N., Pagniez, F., Duflos, M., Le Pape, P., Na, Y. M., Le Baut, G. & Le Borgne, M. (2007). Bioorg. & Med. Chem. Lett. 17, 3686–3689. Web of Science CrossRef CAS Google Scholar
Özel Güven, Ö., Erdoğan, T., Coles, S. J. & Hökelek, T. (2008). Acta Cryst. E64, o1437. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özel Güven, Ö., Tahtacı, H., Coles, S. J. & Hökelek, T. (2010). Acta Cryst. E66, o107–o108. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özel Güven, Ö., Türk, G., Adler, P. D. F., Coles, S. J. & Hökelek, T. (2013). Acta Cryst. E69, o184. CSD CrossRef IUCr Journals Google Scholar
Park, J. S., Yu, K. A., Kang, T. H., Kim, S. & Suh, Y. G. (2007). Bioorg. & Med. Chem. Lett. 17, 3486–3490. Web of Science CrossRef CAS Google Scholar
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979). Acta Cryst. B35, 2461–2464. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Rigaku (2011). 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
The azole antifungals possesing an imidazole ring such as miconazole and econazole have been developed for clinical uses (Godefroi et al., 1969). Some indazole derivatives have been known as antifungal also (Lebouvier et al., 2007; Park et al., 2007). The crystal structure of indazole group containing ketone has been reported recently (Özel Güven et al., 2013). The crystal structures of imidazole ring containg ethers like miconazole (Peeters et al., 1979) and econazole (Freer et al., 1986) have been reported before. The crystal structures of benzimidazole ring containing ether (Özel Güven et al., 2008) and 1,2,4-triazole ring containg ether have been reported previously (Özel Güven et al., 2010). Now, we report herein the crystal structure of the title indazole derivative, (I).
In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The indazole [B (N1/N2/(C9—C15)] ring system is approximately planar with a maximum deviation of -0.031 (2)Å (for atom C12). Its mean plane is oriented with respect to the phenyl [A (C2—C7)] and benzene [ C (C17—C22)] rings at dihedral angles of A/B = 3.17 (4) and B/C = 19.34 (4) °. The dihedral angle between phenyl and benzene rings is A/C = 17.20 (5)°. Atom C8 is 0.016 (2) Å away from the indazole ring plane, while atoms C1 and O1 are -0.026 (2) and 0.599 (1) Å away from the phenyl ring plane. On the other hand, atoms Cl1, Cl2 and C16 are at distances of -0.0258 (5), -0.0693 (5) and -0.074 (2) Å to the benzene ring plane.
In the crystal structure, weak C—H···π interactions (Table 1) may be effective in the stabilization of the structure.