1-(3-Mesityl-3-methyl­cyclo­butyl)-2-phenoxy­ethanone

Koca, M.; Kirilmiş, C.; Arici, C.

doi:10.1107/S1600536810003910

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o523

doi:10.1107/S1600536810003910

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1-(3-Mesityl-3-methylcyclobutyl)-2-phenoxyethanone

Murat Koca,^a Cumhur Kirilmiş ^a and Cengiz Arici ^b ^*

^aDepartment of Chemistry, Faculty of Arts and Science, Adiyaman University, 02040 Adıyaman, Turkey, and ^bDepartment of Engineering Physics, Hacettepe University, Beytepe 06800, Ankara, Turkey
^*Correspondence e-mail: carici.xray@gmail.com

(Received 6 January 2010; accepted 1 February 2010; online 6 February 2010)

In the title compound, C₂₂H₂₆O₂, the cyclobutane ring is puckered, with a dihedral angle of 24.97 (9)° between the two C₃ planes. In the crystal, intermolecular non-classical C—H⋯O interactions between the methylcyclobutyl CH group and the O atom of the phenoxy 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_r = 322.43
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.129
S = 1.07
3921 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) -x+1, -y+2, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

It is well known that three-substituted cyclobutane acid derivatives exhibit anti-inflammatory and anti-depressant activities (Roger et al., 1977; Gerard, 1979) and liquid-crystal properties (Dehmlow & Schmidt, 1990), moreover their of various thiazoles derivatives showed herbicidal (Foerster et al., 1979), anti-inflammatory (Sawhney et al., 1978; Brown et al., 1974), anti-microbial (Suziki et al., 1979) or anti-parasitic activity (Slip et al., 1974). Substituted cyclobutane contained similar structures, have been reported in the recent years (Kirilmiş et al., 2005a, 2005b; Sari et al., 2002, 2004;Çukurovali et al., 2005; Dinçer et al., 2004).

The four-atom bridge O2/C16/C15/C11 linking the cyclobutane and phenoxy rings is planar (Fig. 1). The torsion angle of O2—C16—C15—C11 is -1.0 (1)°. It corresponds to the (-) synclinical configuration. The cyclobutane ring is similar puckered as in a related compounds; the C9/C7/C10 plane forms a dihedaral angle of 24.97 (9)° with the C10/C11/C9 plane in the title compound. The same dihedral angles are presented in the literature: 25.74 (6)° - Çukurovali et al., (2005) and 19.8 (3)° - Dinçer et al., (2004). The mesityl and phenoxy rings are planar. The dihedral angle between these ring is 73.90 (5)°. The maximum deviation from mean plane of the atoms for mesityl and phenoxy rings are -0.046 (6)Å for C5 and 0.016 (3)Å for C17, respectively.

There is one intermolcular non-classical C—H···O hydrogen-bonding interactions in the crystal structure. This interactions lead to close packing between the neighbouring molecules. And the structure is stabilized by van der Waals interactions and symmetry-related molecules are linked to form dimerization chains via C—H···O intermolecular non-classical hydrogen bond. Intermolecular van der Waals interactions between the methylcyclobutyl CH group and the O atom of the phenoxy group (Fig. 2, Table 1).

In the IR spectra of 1-(3-mesityl-3-methylcyclobutyl)-2-phenoxy-1-ethanone very important bonds were observed as (ν, cm^-1); 1711 (sharp C═O stretching) respectively and between 3063–2852 (broad aliphatic and aromatic C—H stretching) and 1070 (ether C–O–C stretching). The ¹H-NMR spectra were reported in p.p.m. (δ) relative to tetramethylsilane (SiMe₄) as the internal standard and referenced to deuterochloroform (CDCl₃). In the ¹H-NMR spectra were H signals obtained as (p.p.m.) 1.7 (s, 3H, cyclobutane-CH₃), 2.2 (s, 9H, CH₃-mesitylene), 2.5–2.9 (m, 4H, cyclobutane CH₂), 3.9 (p,1H, cyclobutane CH), 4.2 (s, 2H, O—CH₂) and aromatic protons observed at 6.7–7.3 (m, 7H, ArH). Elemental Analysis Calc. for C₂₂H₂₆O₂ (322.44 g mol^-1): C, 81.95; H, 8.13 Found: C, 81.88; H, 8.05.

Related literature top

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 top

Elemental analysis were determined on a LECO CHNS–932 auto elemental analysis apparatus. Infrared spectra were obtained by using a Mattson 1000 F T–IR Spectrometer, from 4000–400 cm^-1 in KBr pellet. ¹H-NMR spectra were recorded on a Jeol FX–90Q Spectrometer 90 MHz.

Synthesis of 1-(3-mesityl-3-methylcyclobutyl)-2-phenoxy-1-ethanone: a mixture of 1-mesityl-1-methyl-3-(2-chloro-1-oxoethyl)cyclobutane (2.64 g, 10 mmol), phenol (1.035 g, 11 mmol) and K₂CO₃ (1.51 g, 11 mmol) in 200 ml dry acetone was refluxed for 8 h. The reaction mixture was poured into water (500 ml), the insoluble portion was filtered off, washed with water and crystallized from ethanol (yield 85%).

Computing details top

Data collection: COLLECT (Bruker–Nonius, 2002); cell refinement: EVALCCD (Bruker–Nonius, 2002); data reduction: EVALCCD (Bruker–Nonius, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as a small circles of arbitrary radii.
	Fig. 2. A packing diagram of title compound with the intermolecular H bonds (dashed lines). Symmetry code: (i) -x+1, -y+2, -z+1.

1-(3-Mesityl-3-methylcyclobutyl)-2-phenoxyethanone top

Crystal data top

C₂₂H₂₆O₂	Z = 2
M_r = 322.43	F(000) = 348
Triclinic, P1	D_x = 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

Data collection top

Nonius KappaCCD diffractometer	3921 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 9 pixels mm^-1	θ_max = 27.1°, θ_min = 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
T_min = 0.969, T_max = 0.982	l = −14→14
23641 measured reflections

Refinement top

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(F_o²) + (0.0644P)² + 0.2801P] where P = (F_o² + 2F_c²)/3
3921 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₂₆O₂	γ = 86.235 (2)°
M_r = 322.43	V = 892.24 (19) Å³
Triclinic, P1	Z = 2
a = 8.5884 (12) Å	Mo Kα radiation
b = 10.1725 (11) Å	µ = 0.08 mm⁻¹
c = 11.1018 (12) Å	T = 100 K
α = 82.364 (4)°	0.42 × 0.33 × 0.24 mm
β = 68.170 (3)°

Data collection top

Nonius KappaCCD diffractometer	3921 independent reflections
Absorption correction: multi-scan (SADABS; Bruker–Nonius, 2002)	2968 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.982	R_int = 0.054
23641 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.07	Δρ_max = 0.32 e Å⁻³
3921 reflections	Δρ_min = −0.25 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆O₂
M_r	322.43
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.5884 (12), 10.1725 (11), 11.1018 (12)
α, β, γ (°)	82.364 (4), 68.170 (3), 86.235 (2)
V (Å³)	892.24 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.33 × 0.24

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker–Nonius, 2002)
T_min, T_max	0.969, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	23641, 3921, 2968
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.07
No. of reflections	3921
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: COLLECT (Bruker–Nonius, 2002), EVALCCD (Bruker–Nonius, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Acknowledgements

This study was supported financially by grant DPT/2003 K 120440-1 from the Scientific and Technical Research Council of Turkey (Project Manager Yıldırım Aydogdu). The authors extend special thanks to Frank W. Heinemann for the data collection.

References

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