2-[2-(2,6-Di-chloro-benz-yloxy)-2-phenyl-eth-yl]-2H-indazole.

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 inter-actions link the mol-ecules into supra-molecular chains running along the b-axis direction.

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

C22H18Cl2N2O

M = 397.28

Monoclinic,

a = 15.2399 (4) Å

b = 5.3814 (3) Å

c = 23.0461 (6) Å

β = 90.871 (3)°

V = 1889.84 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 294 K

0.35 × 0.20 × 0.15 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.918, T max = 0.948

18118 measured reflections

4737 independent reflections

3685 reflections with I > 2σ(I)

R int = 0.038

3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.08

4737 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.90 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004887/xu5774sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004887/xu5774Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004887/xu5774Isup3.cml

CCDC reference: 989513

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .