3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetra­hydro-2-naphthoic acid (AHTN–COOH)

Kuhlich, P.; Göstl, R.; Metzinger, R.; Piechotta, C.; Nehls, I.

doi:10.1107/S1600536810038572

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2687

doi:10.1107/S1600536810038572

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3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthoic acid (AHTN–COOH)

Paul Kuhlich,^a ^* Robert Göstl,^b Ramona Metzinger,^b Christian Piechotta ^a and Irene Nehls ^a

^aBAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany, and ^bHumboldt-Universität zu Berlin, Department of Chemistry, Brook-Taylor-Strasse 2, D-12489 Berlin, Germany
^*Correspondence e-mail: paul.kuhlich@bam.de

(Received 23 August 2010; accepted 27 September 2010; online 30 September 2010)

The title compound, C₁₇H₂₄O₂, is the product of a haloform reaction of 6-acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN). The compound is a racemic mixture with a disorder in its aliphatic ring [occupany ratio 0.683 (4):0.317 (4)] due to two possible half-chair forms. The carboxylic acid unit is slightly twisted out of coplanarity with the aromatic system [dihedral angle = 29.26 (6)°]. In the crystal, pairs of short classical intermolecular O—H⋯O hydrogen bonds link pairs of molecules around a center of symmetry.

Related literature

For a similar synthesis of AHTN-COOH and the mechanism of the haloform reaction, see: Valdersnes et al. (2006 ); Fuson & Bull (1934 ). For the crystal structure of AHTN, see: De Ridder et al. (1990 ). For environmental occurrence and estrogenic activity of AHTN, see: Heberer (2003 ); Bitsch et al. (2002 ). For industrial synthesis of AHTN and annual production amounts, see: Sell (2006 ); Kupper et al. (2004 ).

Experimental

Crystal data

C₁₇H₂₄O₂
M_r = 260.36
Monoclinic, P 2₁ /c
a = 8.9718 (2) Å
b = 10.1447 (3) Å
c = 17.7058 (5) Å
β = 112.3100 (19)°
V = 1490.88 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.44 × 0.44 × 0.28 mm

Data collection

Stoe IPDS-2t diffractometer
5695 measured reflections
2933 independent reflections
2525 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.130
S = 1.04
2933 reflections
206 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.91	1.72	2.6305 (16)	178
Symmetry code: (i) -x-1, -y, -z.

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 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: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038572/fl2316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038572/fl2316Isup2.hkl

checkCIF report

Comment top

The title compound is the carboxylic acid AHTN-COOH 2 of 6-acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN) obtained by a Haloform reaction (Fuson & Bull, 1934) of AHTN 1 with sodium hypochlorite solution (NaOCl). The reaction mechanism is shown in Figure 1. A similar synthesis was given by Valdersnes et al. (2006). AHTN-COOH 2 might be a disinfection by-product of AHTN 1.

AHTN itself is a widely used fragrance in cosmetics and cleaning products. Its commonest trade name is Tonalide. The crystal structure of AHTN was shown by De Ridder (De Ridder et al., 1990). AHTN is produced in the ton-scale, in 2000, approx. 343,000 kg (Kupper et al., 2004) and introduced into the environment mainly by sewage treatment plants supplied by municipal wastewater. It can be found in surface water at low µg/L concentration (Heberer, 2003). Due to the low estrogenic potential of AHTN (Bitsch et al., 2002) this might induce a health concern.

The industrial synthesis of AHTN 1 is shown in Figure 2. Both starting chemicals are inexpensive and readily available: para-cymene and neo-hexene, the later results from an olefin metathesis of di-iso-butylene with ethylene (Sell, 2006). AHTN 1 is obtained as racemic mixture in industrial-scale. Hence, the title compound AHTN-COOH 2 is obtained as racemic mixture, too.

The compound (Fig. 3) is crystallizing in the monoclinic space group P21/c. It shows disorder (68:32) within the cyclohexane moiety: the two possible half-chair forms are present.

The compound exhibits a short classical intermolecular H bond which links the molecules into pairs around a center of symmetry (Fig. 4). A summary of these interactions is compiled in Table 1.

Related literature top

For a similar synthesis of AHTN-COOH and the mechanism of the haloform reaction, see: Valdersnes et al. (2006); Fuson & Bull (1934). For the crystal structure of AHTN, see: De Ridder et al. (1990). For environmental occurrence and estrogenic activity of AHTN, see: Heberer (2003); Bitsch et al. (2002). For industrial synthesis of AHTN and annual production amounts, see: Sell (2006); Kupper et al. (2004).

Experimental top

NaOCl was added to a solution of racemic AHTN in acetonitrile. The mixture was stirred for 72 h at room temperature. Afterwards water was added to dissolve precipitated salt, sodium sulfite to quench free chlorine and 6 M hydrochloric acid to adjust the pH to one. The organic layer was extracted with diethyl ether. The extracts were combined, dried over anhydrous sodium sulfate and filtered. Evaporation of the solvent in vacuo gave a white crystalline residue that was washed with cyclohexane. Recrystallization from diethyl ether resulted in colorless crystals [m.p. 497 K]. IR (ν, cm^-1): 1675(s), 1609(s), 1550(s), 1498(s), 1364(s), 1305(s), 1262(s), 1247(s), 1111(s), 912(s), 885(s), 850(s); ¹H-NMR (500 MHz; CD₃OD; TMS): δ [ppm] = 7.88 (1H, s), 7.24 (1H, s), 2.52 (3H, s), 1.89 (1H, m), 1.64 (1H, dd, ²J=13.3Hz, ³J=13.3Hz), 1.41 (1H, dd, ²J=13.5Hz, ³J=2.6Hz), 1.33 (3H, s), 1.30 (3H, s), 1.25 (3H, s), 1.07 (3H, s), 1.01 (3H, d, J=6.9Hz); ¹³C-NMR (125 MHz, CD₃OD, TMS): δ [ppm] = 171.5, 151.6, 143.4, 137.8, 131.3, 130.5, 128.5, 44.7, 38.9, 35.8, 35.0, 32.8, 32.4, 28.9, 25.1, 21.9, 17.3; (+)-ESI/MS: 261.5 (40) [M+H⁺], 283.5 (100) [M+Na⁺].

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. Haloform reaction of AHTN 1 to result in AHTN-COOH 2.
	Fig. 2. Industrial production of AHTN 1.
	Fig. 3. Displacement parameter plots of the two half-chair conformations in the crystal structure. Displacement ellipsoids are set to 30% probability, H atoms were excluded for clarity.
	Fig. 4. Packing diagram of the unit-cell content, view direction [0 1 0]. All H atoms are excluded except for the one involved in H bond formation. Only one conformer is shown.

3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthoic acid top

Crystal data top

C₁₇H₂₄O₂	F(000) = 568
M_r = 260.36	D_x = 1.160 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 30064 reflections
a = 8.9718 (2) Å	θ = 2.3–30.9°
b = 10.1447 (3) Å	µ = 0.07 mm⁻¹
c = 17.7058 (5) Å	T = 100 K
β = 112.3100 (19)°	Fragment, colourless
V = 1490.88 (7) Å³	0.44 × 0.44 × 0.28 mm
Z = 4

Data collection top

Stoe IPDS-2t diffractometer	2525 reflections with I > 2σ(I)
Radiation source: long fine focus sealed X-ray tube	R_int = 0.016
Planar graphite monochromator	θ_max = 26.0°, θ_min = 2.8°
Detector resolution: 6.67 pixels mm^-1	h = −11→10
ω–rotation,ω–incr.=1°,319 exposures scans	k = −12→12
5695 measured reflections	l = −21→10
2933 independent 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) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0771P)² + 0.4377P] where P = (F_o² + 2F_c²)/3
2933 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.29 e Å⁻³
30 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₇H₂₄O₂	V = 1490.88 (7) Å³
M_r = 260.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9718 (2) Å	µ = 0.07 mm⁻¹
b = 10.1447 (3) Å	T = 100 K
c = 17.7058 (5) Å	0.44 × 0.44 × 0.28 mm
β = 112.3100 (19)°

Data collection top

Stoe IPDS-2t diffractometer	2525 reflections with I > 2σ(I)
5695 measured reflections	R_int = 0.016
2933 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	30 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
2933 reflections	Δρ_min = −0.34 e Å⁻³
206 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.40903 (12)	0.07719 (11)	−0.05516 (6)	0.0301 (3)
O2	−0.31528 (12)	0.04014 (11)	0.07904 (6)	0.0274 (3)
H2	−0.4096	−0.0008	0.0723	0.099 (10)*
C1	−0.30126 (16)	0.08804 (13)	0.01415 (8)	0.0198 (3)
C2	−0.14885 (15)	0.15904 (13)	0.02749 (8)	0.0191 (3)
C3	−0.07123 (16)	0.22058 (13)	0.10232 (8)	0.0192 (3)
H3	−0.1154	0.2127	0.1419	0.029*
C4	0.06989 (16)	0.29353 (13)	0.12086 (8)	0.0192 (3)
C5	0.13789 (16)	0.30168 (13)	0.06178 (8)	0.0196 (3)
C6	0.05971 (16)	0.23646 (14)	−0.01268 (8)	0.0230 (3)
H6	0.1069	0.2400	−0.0512	0.034*
C7	−0.08302 (16)	0.16713 (14)	−0.03275 (8)	0.0219 (3)
C8	−0.15681 (19)	0.10224 (17)	−0.11538 (9)	0.0316 (4)
H8A	−0.2521	0.1494	−0.1483	0.047*
H8B	−0.1846	0.0128	−0.1088	0.047*
H8C	−0.0807	0.1032	−0.1416	0.047*
C9	0.29440 (16)	0.37676 (14)	0.07460 (8)	0.0231 (3)
C10A	0.3364 (4)	0.4704 (4)	0.1476 (2)	0.0292 (7)	0.683 (4)
H10A	0.2582	0.5428	0.1321	0.044*	0.683 (4)
C11A	0.3210 (3)	0.3998 (3)	0.21971 (13)	0.0272 (7)	0.683 (4)
H11A	0.3627	0.4560	0.2675	0.041*	0.683 (4)
H11B	0.3858	0.3202	0.2310	0.041*	0.683 (4)
C15A	0.5059 (12)	0.5308 (12)	0.1732 (6)	0.0497 (14)	0.683 (4)
H15A	0.5265	0.5866	0.2198	0.075*	0.683 (4)
H15B	0.5123	0.5819	0.1288	0.075*	0.683 (4)
H15C	0.5847	0.4615	0.1867	0.075*	0.683 (4)
C10B	0.3736 (8)	0.4188 (8)	0.1699 (4)	0.0292 (15)	0.317 (4)
H10B	0.4204	0.3404	0.2026	0.044*	0.317 (4)
C11B	0.2488 (7)	0.4758 (5)	0.1983 (3)	0.0297 (14)	0.317 (4)
H11C	0.1851	0.5417	0.1600	0.045*	0.317 (4)
H11D	0.3005	0.5171	0.2513	0.045*	0.317 (4)
C15B	0.507 (3)	0.524 (3)	0.1870 (15)	0.0497 (14)	0.317 (4)
H15D	0.4578	0.6093	0.1706	0.075*	0.317 (4)
H15E	0.5725	0.5038	0.1568	0.075*	0.317 (4)
H15F	0.5720	0.5256	0.2443	0.075*	0.317 (4)
C14A	0.0479 (4)	0.4785 (3)	0.20837 (16)	0.0297 (6)	0.683 (4)
H14A	−0.0611	0.4526	0.1978	0.045*	0.683 (4)
H14B	0.0488	0.5422	0.1684	0.045*	0.683 (4)
H14C	0.0947	0.5166	0.2619	0.045*	0.683 (4)
C14B	−0.0085 (8)	0.4464 (7)	0.2128 (4)	0.0297 (6)	0.317 (4)
H14D	0.0298	0.4937	0.2635	0.045*	0.317 (4)
H14E	−0.0922	0.3865	0.2118	0.045*	0.317 (4)
H14F	−0.0504	0.5075	0.1683	0.045*	0.317 (4)
C12	0.14176 (18)	0.36242 (15)	0.20370 (8)	0.0261 (3)
C13	0.1649 (2)	0.26665 (17)	0.27301 (9)	0.0393 (4)
H13A	0.2261	0.3084	0.3241	0.059*
H13B	0.2217	0.1902	0.2663	0.059*
H13C	0.0617	0.2407	0.2725	0.059*
C16	0.42374 (19)	0.27774 (17)	0.07668 (13)	0.0408 (4)
H16A	0.5219	0.3237	0.0843	0.061*
H16B	0.3887	0.2300	0.0261	0.061*
H16C	0.4420	0.2172	0.1210	0.061*
C17	0.2657 (2)	0.4705 (2)	0.00255 (13)	0.0492 (5)
H17A	0.1800	0.5304	−0.0016	0.074*
H17B	0.2367	0.4204	−0.0470	0.074*
H17C	0.3623	0.5195	0.0111	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0218 (5)	0.0408 (6)	0.0227 (5)	−0.0104 (4)	0.0028 (4)	−0.0008 (4)
O2	0.0213 (5)	0.0348 (6)	0.0255 (5)	−0.0064 (4)	0.0081 (4)	0.0061 (4)
C1	0.0183 (6)	0.0202 (6)	0.0202 (6)	−0.0005 (5)	0.0066 (5)	0.0002 (5)
C2	0.0172 (6)	0.0191 (7)	0.0203 (6)	−0.0001 (5)	0.0063 (5)	0.0007 (5)
C3	0.0206 (6)	0.0198 (7)	0.0187 (6)	0.0008 (5)	0.0092 (5)	0.0012 (5)
C4	0.0200 (6)	0.0170 (6)	0.0185 (6)	−0.0001 (5)	0.0050 (5)	−0.0002 (5)
C5	0.0177 (6)	0.0175 (6)	0.0227 (6)	−0.0001 (5)	0.0067 (5)	0.0012 (5)
C6	0.0238 (7)	0.0266 (7)	0.0223 (7)	−0.0025 (5)	0.0130 (6)	−0.0021 (5)
C7	0.0228 (7)	0.0233 (7)	0.0197 (6)	−0.0024 (5)	0.0081 (5)	−0.0024 (5)
C8	0.0328 (8)	0.0414 (9)	0.0230 (7)	−0.0119 (7)	0.0135 (6)	−0.0100 (6)
C9	0.0188 (7)	0.0235 (7)	0.0271 (7)	−0.0041 (5)	0.0088 (5)	−0.0006 (6)
C10A	0.0318 (16)	0.0283 (16)	0.0270 (15)	−0.0133 (12)	0.0106 (12)	−0.0039 (12)
C11A	0.0238 (12)	0.0336 (15)	0.0201 (10)	−0.0111 (11)	0.0038 (9)	−0.0039 (10)
C15A	0.0487 (12)	0.068 (2)	0.036 (4)	−0.0383 (13)	0.019 (2)	−0.016 (2)
C10B	0.026 (3)	0.026 (3)	0.028 (3)	−0.006 (2)	0.001 (2)	0.004 (2)
C11B	0.038 (3)	0.023 (3)	0.024 (2)	−0.006 (2)	0.006 (2)	−0.000 (2)
C15B	0.0487 (12)	0.068 (2)	0.036 (4)	−0.0383 (13)	0.019 (2)	−0.016 (2)
C14A	0.0400 (18)	0.0209 (14)	0.0221 (9)	−0.0016 (11)	0.0048 (11)	−0.0056 (9)
C14B	0.0400 (18)	0.0209 (14)	0.0221 (9)	−0.0016 (11)	0.0048 (11)	−0.0056 (9)
C12	0.0300 (7)	0.0291 (8)	0.0189 (6)	−0.0107 (6)	0.0087 (5)	−0.0050 (6)
C13	0.0526 (10)	0.0349 (9)	0.0199 (7)	0.0117 (8)	0.0020 (7)	0.0004 (6)
C16	0.0247 (8)	0.0343 (9)	0.0677 (12)	−0.0011 (7)	0.0224 (8)	0.0013 (8)
C17	0.0290 (9)	0.0488 (11)	0.0625 (12)	−0.0103 (8)	0.0092 (8)	0.0271 (9)

Geometric parameters (Å, º) top

O1—C1	1.2458 (17)	C15A—H15B	0.9600
O2—C1	1.2969 (16)	C15A—H15C	0.9600
O2—H2	0.9088	C10B—C11B	1.505 (9)
C1—C2	1.4830 (18)	C10B—C15B	1.546 (12)
C2—C3	1.3892 (18)	C10B—H10B	0.9800
C2—C7	1.4040 (18)	C11B—C12	1.524 (5)
C3—C4	1.3939 (19)	C11B—H11C	0.9700
C3—H3	0.9300	C11B—H11D	0.9700
C4—C5	1.3992 (19)	C15B—H15D	0.9600
C4—C12	1.5289 (18)	C15B—H15E	0.9600
C5—C6	1.4020 (19)	C15B—H15F	0.9600
C5—C9	1.5366 (18)	C14A—C12	1.468 (3)
C6—C7	1.3839 (19)	C14A—H14A	0.9600
C6—H6	0.9300	C14A—H14B	0.9600
C7—C8	1.5089 (18)	C14A—H14C	0.9600
C8—H8A	0.9600	C14B—C12	1.653 (7)
C8—H8B	0.9600	C14B—H14D	0.9600
C8—H8C	0.9600	C14B—H14E	0.9600
C9—C16	1.525 (2)	C14B—H14F	0.9600
C9—C10A	1.532 (3)	C12—C13	1.516 (2)
C9—C17	1.533 (2)	C13—H13A	0.9600
C9—C10B	1.620 (6)	C13—H13B	0.9600
C10A—C11A	1.515 (4)	C13—H13C	0.9600
C10A—C15A	1.540 (7)	C16—H16A	0.9600
C10A—H10A	0.9800	C16—H16B	0.9600
C11A—C12	1.570 (3)	C16—H16C	0.9600
C11A—H11A	0.9700	C17—H17A	0.9600
C11A—H11B	0.9700	C17—H17B	0.9600
C15A—H15A	0.9600	C17—H17C	0.9600

C1—O2—H2	117.0	C15B—C10B—C9	112.8 (11)
O1—C1—O2	122.65 (12)	C11B—C10B—H10B	108.7
O1—C1—C2	121.59 (12)	C15B—C10B—H10B	108.7
O2—C1—C2	115.76 (11)	C9—C10B—H10B	108.7
C3—C2—C7	119.68 (12)	C10B—C11B—C12	107.3 (4)
C3—C2—C1	117.92 (11)	C10B—C11B—H11C	110.3
C7—C2—C1	122.39 (12)	C12—C11B—H11C	110.3
C2—C3—C4	123.01 (12)	C10B—C11B—H11D	110.3
C2—C3—H3	118.5	C12—C11B—H11D	110.3
C4—C3—H3	118.5	H11C—C11B—H11D	108.5
C3—C4—C5	118.05 (12)	C10B—C15B—H15D	109.5
C3—C4—C12	118.89 (12)	C10B—C15B—H15E	109.5
C5—C4—C12	123.05 (12)	H15D—C15B—H15E	109.5
C4—C5—C6	118.07 (12)	C10B—C15B—H15F	109.5
C4—C5—C9	123.51 (12)	H15D—C15B—H15F	109.5
C6—C5—C9	118.41 (11)	H15E—C15B—H15F	109.5
C7—C6—C5	124.41 (12)	C12—C14A—H14A	109.5
C7—C6—H6	117.8	C12—C14A—H14B	109.5
C5—C6—H6	117.8	C12—C14A—H14C	109.5
C6—C7—C2	116.73 (12)	C12—C14B—H14D	109.5
C6—C7—C8	119.56 (12)	C12—C14B—H14E	109.5
C2—C7—C8	123.70 (12)	C12—C14B—H14F	109.5
C7—C8—H8A	109.5	C14A—C12—C13	111.94 (16)
C7—C8—H8B	109.5	C13—C12—C11B	129.6 (2)
H8A—C8—H8B	109.5	C14A—C12—C4	112.25 (15)
C7—C8—H8C	109.5	C13—C12—C4	111.21 (12)
H8A—C8—H8C	109.5	C11B—C12—C4	109.3 (2)
H8B—C8—H8C	109.5	C14A—C12—C11A	111.49 (18)
C16—C9—C10A	116.56 (19)	C13—C12—C11A	101.08 (15)
C16—C9—C17	108.36 (14)	C4—C12—C11A	108.28 (12)
C10A—C9—C17	103.15 (19)	C13—C12—C14B	96.8 (3)
C16—C9—C5	108.75 (12)	C11B—C12—C14B	100.0 (3)
C10A—C9—C5	110.50 (14)	C4—C12—C14B	105.4 (2)
C17—C9—C5	109.21 (12)	C12—C13—H13A	109.5
C16—C9—C10B	96.9 (3)	C12—C13—H13B	109.5
C17—C9—C10B	124.9 (3)	H13A—C13—H13B	109.5
C5—C9—C10B	107.4 (2)	C12—C13—H13C	109.5
C11A—C10A—C9	110.2 (2)	H13A—C13—H13C	109.5
C11A—C10A—C15A	109.7 (4)	H13B—C13—H13C	109.5
C9—C10A—C15A	113.2 (5)	C9—C16—H16A	109.5
C11A—C10A—H10A	107.9	C9—C16—H16B	109.5
C9—C10A—H10A	107.9	H16A—C16—H16B	109.5
C15A—C10A—H10A	107.9	C9—C16—H16C	109.5
C10A—C11A—C12	112.1 (2)	H16A—C16—H16C	109.5
C10A—C11A—H11A	109.2	H16B—C16—H16C	109.5
C12—C11A—H11A	109.2	C9—C17—H17A	109.5
C10A—C11A—H11B	109.2	C9—C17—H17B	109.5
C12—C11A—H11B	109.2	H17A—C17—H17B	109.5
H11A—C11A—H11B	107.9	C9—C17—H17C	109.5
C11B—C10B—C15B	106.6 (14)	H17A—C17—H17C	109.5
C11B—C10B—C9	111.2 (5)	H17B—C17—H17C	109.5

O1—C1—C2—C3	150.42 (13)	C5—C9—C10A—C15A	170.1 (5)
O2—C1—C2—C3	−28.69 (18)	C10B—C9—C10A—C15A	83.1 (9)
O1—C1—C2—C7	−28.8 (2)	C9—C10A—C11A—C12	−67.0 (3)
O2—C1—C2—C7	152.14 (13)	C15A—C10A—C11A—C12	167.7 (6)
C7—C2—C3—C4	1.2 (2)	C16—C9—C10B—C11B	−157.8 (5)
C1—C2—C3—C4	−177.96 (12)	C10A—C9—C10B—C11B	55.8 (7)
C2—C3—C4—C5	−1.7 (2)	C17—C9—C10B—C11B	84.1 (5)
C2—C3—C4—C12	177.34 (12)	C5—C9—C10B—C11B	−45.6 (6)
C3—C4—C5—C6	0.27 (19)	C16—C9—C10B—C15B	82.6 (15)
C12—C4—C5—C6	−178.78 (13)	C10A—C9—C10B—C15B	−63.9 (16)
C3—C4—C5—C9	−178.97 (12)	C17—C9—C10B—C15B	−35.5 (15)
C12—C4—C5—C9	2.0 (2)	C5—C9—C10B—C15B	−165.3 (14)
C4—C5—C6—C7	1.8 (2)	C15B—C10B—C11B—C12	−164.9 (11)
C9—C5—C6—C7	−178.93 (13)	C9—C10B—C11B—C12	71.8 (6)
C5—C6—C7—C2	−2.3 (2)	C10B—C11B—C12—C14A	−166.0 (4)
C5—C6—C7—C8	179.27 (14)	C10B—C11B—C12—C13	85.6 (4)
C3—C2—C7—C6	0.74 (19)	C10B—C11B—C12—C4	−56.4 (5)
C1—C2—C7—C6	179.90 (12)	C10B—C11B—C12—C11A	38.6 (4)
C3—C2—C7—C8	179.11 (13)	C10B—C11B—C12—C14B	−166.8 (5)
C1—C2—C7—C8	−1.7 (2)	C3—C4—C12—C14A	−73.3 (2)
C4—C5—C9—C16	113.07 (15)	C5—C4—C12—C14A	105.7 (2)
C6—C5—C9—C16	−66.16 (17)	C3—C4—C12—C13	52.99 (17)
C4—C5—C9—C10A	−16.1 (2)	C5—C4—C12—C13	−127.97 (15)
C6—C5—C9—C10A	164.7 (2)	C3—C4—C12—C11B	−157.5 (3)
C4—C5—C9—C17	−128.86 (16)	C5—C4—C12—C11B	21.5 (3)
C6—C5—C9—C17	51.91 (18)	C3—C4—C12—C11A	163.19 (15)
C4—C5—C9—C10B	9.2 (3)	C5—C4—C12—C11A	−17.8 (2)
C6—C5—C9—C10B	−170.0 (3)	C3—C4—C12—C14B	−50.8 (3)
C16—C9—C10A—C11A	−78.0 (3)	C5—C4—C12—C14B	128.2 (3)
C17—C9—C10A—C11A	163.4 (2)	C10A—C11A—C12—C14A	−74.4 (3)
C5—C9—C10A—C11A	46.8 (3)	C10A—C11A—C12—C13	166.5 (2)
C10B—C9—C10A—C11A	−40.1 (6)	C10A—C11A—C12—C11B	−48.5 (3)
C16—C9—C10A—C15A	45.3 (6)	C10A—C11A—C12—C4	49.6 (3)
C17—C9—C10A—C15A	−73.3 (6)	C10A—C11A—C12—C14B	−83.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.91	1.72	2.6305 (16)	178

Symmetry code: (i) −x−1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₄O₂
M_r	260.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.9718 (2), 10.1447 (3), 17.7058 (5)
β (°)	112.3100 (19)
V (Å³)	1490.88 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.44 × 0.44 × 0.28

Data collection
Diffractometer	Stoe IPDS2t diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5695, 2933, 2525
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.130, 1.04
No. of reflections	2933
No. of parameters	206
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 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
O2—H2···O1ⁱ	0.91	1.72	2.6305 (16)	178

Symmetry code: (i) −x−1, −y, −z.

Acknowledgements

The authors wish to thank Dr Beatrice Braun (Humboldt University, Berlin, Institute of Chemistry) for providing diffractometer time and helping with the interpretation of the data.

References

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