1-(3-Mesityl-3-methyl-cyclo-butyl)-2-phenoxy-ethanone.

In the title compound, C(22)H(26)O(2), the cyclo-butane ring is puckered, with a dihedral angle of 24.97 (9)° between the two C(3) planes. In the crystal, inter-molecular non-classical C-H⋯O inter-actions between the methyl-cyclo-butyl CH group and the O atom of the phen-oxy group are found.

Related literature

For related cyclo­butanes, see: Çukurovali et al. (2005 ▶); Dinçer et al. (2004 ▶); Kirilmiş et al. (2005a ▶,b ▶); Sari et al. (2002 ▶, 2004 ▶). For the anti-inflammatory and anti-depressant activity of three-substituted cyclo­butane acid derivatives, see: Roger et al. (1977 ▶); Gerard (1979 ▶); Sawhney et al. (1978 ▶); Brown et al. (1974 ▶); for anti-microbial activity, see: Suziki et al. (1979 ▶); for anti-parasitic activity, see: Slip et al. (1974 ▶), for herbicidal activity, see: Foerster et al. (1979 ▶) and for their liquid-crystal properties, see: Dehmlow & Schmidt (1990 ▶).

Experimental

Crystal data

C22H26O2

M = 322.43

Triclinic,

a = 8.5884 (12) Å

b = 10.1725 (11) Å

c = 11.1018 (12) Å

α = 82.364 (4)°

β = 68.170 (3)°

γ = 86.235 (2)°

V = 892.24 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.42 × 0.33 × 0.24 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker–Nonius, 2002 ▶) T min = 0.969, T max = 0.982

23641 measured reflections

3921 independent reflections

2968 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.07

3921 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Bruker–Nonius, 2002 ▶); cell refinement: EVALCCD (Bruker–Nonius, 2002 ▶); data reduction: EVALCCD program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003910/rk2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003910/rk2189Isup2.hkl

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

C22H26O2	Z = 2
Mr = 322.43	F(000) = 348
Triclinic, P1	Dx = 1.200 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5884 (12) Å	Cell parameters from 149 reflections
b = 10.1725 (11) Å	θ = 6.0–20.0°
c = 11.1018 (12) Å	µ = 0.08 mm−1
α = 82.364 (4)°	T = 100 K
β = 68.170 (3)°	Block, colourless
γ = 86.235 (2)°	0.42 × 0.33 × 0.24 mm
V = 892.24 (19) Å3

Nonius KappaCCD diffractometer	3921 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 9 pixels mm-1	θmax = 27.1°, θmin = 3.0°
ω–scans with 2.00° and 40 sec per frame	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker–Nonius, 2002)	k = −13→12
Tmin = 0.969, Tmax = 0.982	l = −14→14
23641 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.2801P] where P = (Fo2 + 2Fc2)/3
3921 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.66157 (19)	0.63782 (15)	0.69324 (15)	0.0191 (3)
C2	0.6658 (2)	0.62422 (15)	0.81884 (15)	0.0212 (3)
H2	0.5724	0.5864	0.8899	0.025*
C3	0.8017 (2)	0.66400 (15)	0.84382 (15)	0.0216 (3)
C4	0.9374 (2)	0.71600 (15)	0.73790 (15)	0.0202 (3)
H4	1.0328	0.7416	0.7525	0.024*
C5	0.93938 (19)	0.73229 (15)	0.61020 (15)	0.0181 (3)
C6	0.79712 (19)	0.69657 (14)	0.58680 (15)	0.0168 (3)
C7	0.79622 (18)	0.71572 (15)	0.44807 (15)	0.0175 (3)
C8	0.8730 (2)	0.59338 (16)	0.37804 (16)	0.0238 (4)
H8A	0.8710	0.6069	0.2895	0.036*
H8B	0.8079	0.5150	0.4267	0.036*
H8C	0.9892	0.5802	0.3731	0.036*
C9	0.86927 (19)	0.84742 (16)	0.36088 (15)	0.0190 (3)
H9A	0.8701	0.9204	0.4114	0.023*
H9B	0.9806	0.8360	0.2918	0.023*
C10	0.62618 (19)	0.75748 (15)	0.42989 (15)	0.0189 (3)
H10B	0.5741	0.6854	0.4069	0.023*
H10A	0.5440	0.7998	0.5038	0.023*
C11	0.72371 (19)	0.85766 (15)	0.31115 (15)	0.0181 (3)
H11	0.7558	0.8179	0.2273	0.022*
C12	0.5091 (2)	0.58448 (17)	0.67897 (17)	0.0255 (4)
H12A	0.5442	0.5430	0.5980	0.038*
H12B	0.4298	0.6575	0.6761	0.038*
H12C	0.4549	0.5185	0.7536	0.038*
C13	0.8009 (2)	0.64947 (18)	0.98136 (16)	0.0283 (4)
H13A	0.7400	0.5695	1.0308	0.042*
H13B	0.7456	0.7273	1.0240	0.042*
H13C	0.9166	0.6421	0.9784	0.042*
C14	1.09987 (19)	0.78228 (18)	0.50263 (16)	0.0233 (4)
H14A	1.1277	0.7295	0.4294	0.035*
H14B	1.1912	0.7741	0.5361	0.035*
H14C	1.0846	0.8756	0.4727	0.035*
C15	0.63834 (19)	0.98988 (16)	0.30363 (15)	0.0196 (3)
C16	0.4891 (2)	1.00148 (15)	0.26088 (16)	0.0217 (3)
H16A	0.3888	1.0322	0.3314	0.026*
H16B	0.5121	1.0673	0.1824	0.026*
C17	0.35862 (19)	0.87125 (16)	0.16126 (15)	0.0193 (3)
C18	0.2842 (2)	0.98135 (16)	0.11452 (16)	0.0231 (4)
H18	0.2968	1.0674	0.1337	0.028*
C19	0.1910 (2)	0.96324 (19)	0.03910 (18)	0.0302 (4)
H19	0.1404	1.0381	0.0062	0.036*
C20	0.1703 (2)	0.8385 (2)	0.01108 (17)	0.0304 (4)
H20	0.1088	0.8280	−0.0425	0.036*
C21	0.2405 (2)	0.72904 (18)	0.06224 (18)	0.0290 (4)
H21	0.2240	0.6427	0.0459	0.035*
C22	0.3340 (2)	0.74507 (17)	0.13673 (17)	0.0253 (4)
H22	0.3819	0.6697	0.1714	0.030*
O1	0.68046 (15)	1.08915 (12)	0.33319 (12)	0.0270 (3)
O2	0.45853 (14)	0.87559 (11)	0.23207 (11)	0.0235 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (8)	0.0117 (7)	0.0253 (8)	−0.0002 (6)	−0.0076 (6)	−0.0015 (6)
C2	0.0221 (8)	0.0149 (8)	0.0224 (8)	−0.0030 (6)	−0.0038 (7)	0.0004 (6)
C3	0.0289 (9)	0.0143 (7)	0.0217 (8)	−0.0001 (6)	−0.0088 (7)	−0.0040 (6)
C4	0.0214 (8)	0.0183 (8)	0.0239 (8)	−0.0011 (6)	−0.0104 (7)	−0.0058 (6)
C5	0.0179 (7)	0.0156 (7)	0.0211 (8)	0.0010 (6)	−0.0066 (6)	−0.0056 (6)
C6	0.0179 (7)	0.0129 (7)	0.0203 (7)	0.0013 (6)	−0.0069 (6)	−0.0047 (6)
C7	0.0159 (7)	0.0175 (8)	0.0198 (7)	−0.0008 (6)	−0.0066 (6)	−0.0043 (6)
C8	0.0258 (8)	0.0229 (8)	0.0263 (8)	0.0048 (7)	−0.0122 (7)	−0.0099 (7)
C9	0.0168 (7)	0.0216 (8)	0.0177 (7)	−0.0018 (6)	−0.0047 (6)	−0.0035 (6)
C10	0.0174 (7)	0.0177 (8)	0.0237 (8)	−0.0006 (6)	−0.0094 (6)	−0.0039 (6)
C11	0.0187 (7)	0.0190 (8)	0.0182 (7)	−0.0002 (6)	−0.0078 (6)	−0.0048 (6)
C12	0.0228 (8)	0.0225 (9)	0.0302 (9)	−0.0085 (7)	−0.0104 (7)	0.0061 (7)
C13	0.0371 (10)	0.0267 (9)	0.0210 (8)	−0.0066 (8)	−0.0103 (7)	−0.0013 (7)
C14	0.0171 (8)	0.0321 (9)	0.0218 (8)	−0.0037 (7)	−0.0072 (7)	−0.0049 (7)
C15	0.0203 (8)	0.0197 (8)	0.0174 (7)	−0.0029 (6)	−0.0048 (6)	−0.0026 (6)
C16	0.0219 (8)	0.0167 (8)	0.0282 (8)	0.0012 (6)	−0.0099 (7)	−0.0070 (7)
C17	0.0148 (7)	0.0211 (8)	0.0218 (8)	0.0001 (6)	−0.0062 (6)	−0.0036 (6)
C18	0.0218 (8)	0.0190 (8)	0.0277 (8)	−0.0038 (6)	−0.0093 (7)	0.0018 (7)
C19	0.0283 (9)	0.0314 (10)	0.0328 (9)	−0.0060 (7)	−0.0169 (8)	0.0095 (8)
C20	0.0268 (9)	0.0434 (11)	0.0240 (9)	−0.0084 (8)	−0.0121 (7)	−0.0023 (8)
C21	0.0248 (9)	0.0301 (9)	0.0351 (10)	0.0000 (7)	−0.0106 (8)	−0.0154 (8)
C22	0.0215 (8)	0.0204 (8)	0.0365 (9)	0.0040 (7)	−0.0124 (7)	−0.0081 (7)
O1	0.0317 (7)	0.0214 (6)	0.0334 (7)	−0.0009 (5)	−0.0166 (6)	−0.0082 (5)
O2	0.0276 (6)	0.0151 (6)	0.0350 (6)	0.0000 (5)	−0.0196 (5)	−0.0036 (5)

C1—C2	1.397 (2)	C12—H12A	0.9800
C1—C6	1.410 (2)	C12—H12B	0.9800
C1—C12	1.518 (2)	C12—H12C	0.9800
C2—C3	1.392 (2)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.385 (2)	C13—H13C	0.9800
C3—C13	1.512 (2)	C14—H14A	0.9800
C4—C5	1.399 (2)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.418 (2)	C15—O1	1.2177 (19)
C5—C14	1.514 (2)	C15—C16	1.516 (2)
C6—C7	1.529 (2)	C16—O2	1.4237 (18)
C7—C8	1.535 (2)	C16—H16A	0.9900
C7—C9	1.562 (2)	C16—H16B	0.9900
C7—C10	1.571 (2)	C17—O2	1.3682 (18)
C8—H8A	0.9800	C17—C18	1.389 (2)
C8—H8B	0.9800	C17—C22	1.392 (2)
C8—H8C	0.9800	C18—C19	1.391 (2)
C9—C11	1.536 (2)	C18—H18	0.9500
C9—H9A	0.9900	C19—C20	1.383 (3)
C9—H9B	0.9900	C19—H19	0.9500
C10—C11	1.553 (2)	C20—C21	1.387 (3)
C10—H10B	0.9900	C20—H20	0.9500
C10—H10A	0.9900	C21—C22	1.380 (2)
C11—C15	1.497 (2)	C21—H21	0.9500
C11—H11	1.0000	C22—H22	0.9500
C2—C1—C6	119.74 (14)	C10—C11—H11	111.2
C2—C1—C12	116.96 (14)	C1—C12—H12A	109.5
C6—C1—C12	123.28 (14)	C1—C12—H12B	109.5
C3—C2—C1	122.43 (15)	H12A—C12—H12B	109.5
C3—C2—H2	118.8	C1—C12—H12C	109.5
C1—C2—H2	118.8	H12A—C12—H12C	109.5
C4—C3—C2	117.38 (14)	H12B—C12—H12C	109.5
C4—C3—C13	121.65 (15)	C3—C13—H13A	109.5
C2—C3—C13	120.97 (15)	C3—C13—H13B	109.5
C3—C4—C5	122.47 (15)	H13A—C13—H13B	109.5
C3—C4—H4	118.8	C3—C13—H13C	109.5
C5—C4—H4	118.8	H13A—C13—H13C	109.5
C4—C5—C6	119.57 (14)	H13B—C13—H13C	109.5
C4—C5—C14	116.94 (14)	C5—C14—H14A	109.5
C6—C5—C14	123.43 (13)	C5—C14—H14B	109.5
C1—C6—C5	118.27 (14)	H14A—C14—H14B	109.5
C1—C6—C7	121.45 (13)	C5—C14—H14C	109.5
C5—C6—C7	120.21 (13)	H14A—C14—H14C	109.5
C6—C7—C8	110.39 (12)	H14B—C14—H14C	109.5
C6—C7—C9	117.38 (12)	O1—C15—C11	123.12 (14)
C8—C7—C9	111.83 (13)	O1—C15—C16	117.80 (14)
C6—C7—C10	118.07 (12)	C11—C15—C16	119.06 (13)
C8—C7—C10	110.26 (12)	O2—C16—C15	109.41 (13)
C9—C7—C10	87.08 (11)	O2—C16—H16A	109.8
C7—C8—H8A	109.5	C15—C16—H16A	109.8
C7—C8—H8B	109.5	O2—C16—H16B	109.8
H8A—C8—H8B	109.5	C15—C16—H16B	109.8
C7—C8—H8C	109.5	H16A—C16—H16B	108.2
H8A—C8—H8C	109.5	O2—C17—C18	124.76 (14)
H8B—C8—H8C	109.5	O2—C17—C22	115.14 (14)
C11—C9—C7	89.84 (11)	C18—C17—C22	120.10 (15)
C11—C9—H9A	113.7	C17—C18—C19	118.77 (16)
C7—C9—H9A	113.7	C17—C18—H18	120.6
C11—C9—H9B	113.7	C19—C18—H18	120.6
C7—C9—H9B	113.7	C20—C19—C18	121.37 (17)
H9A—C9—H9B	110.9	C20—C19—H19	119.3
C11—C10—C7	88.89 (11)	C18—C19—H19	119.3
C11—C10—H10B	113.8	C19—C20—C21	119.17 (16)
C7—C10—H10B	113.8	C19—C20—H20	120.4
C11—C10—H10A	113.8	C21—C20—H20	120.4
C7—C10—H10A	113.8	C22—C21—C20	120.27 (16)
H10B—C10—H10A	111.1	C22—C21—H21	119.9
C15—C11—C9	117.93 (13)	C20—C21—H21	119.9
C15—C11—C10	114.89 (13)	C21—C22—C17	120.25 (16)
C9—C11—C10	88.64 (11)	C21—C22—H22	119.9
C15—C11—H11	111.2	C17—C22—H22	119.9
C9—C11—H11	111.2	C17—O2—C16	118.20 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.99	2.44	3.419 (3)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.99	2.44	3.419 (3)	172 (2)

Symmetry code: (i) .